The relationship between Hirshfeld potential and cytotoxic activity: A study along a series of flavonoid and chromanone derivatives

Article abstract of DOI:10.1107/S205322962000813X

The present study examines a series of six biologically-active flavonoid and chromanone derivatives by X-ray crystal structure analysis: (E)-3-benzyl-idene-2-phenyl-chroman-4-one, C 22 H 16 O 2, I, (E)-3-(4-methyl-benzyl-idene)-2-phenyl-chroman-4-one, C 23 H 18 O 2, II, (E)-3-(3-methyl-benzyl-idene)-2-phenyl-chroman-4-one, C 23 H 18 O 2, III, (E)-3-(4-meth-oxy-benzyl-idene)-2-phenyl-chroman-4-one, C 23 H 18 O 3, IV, (E)-3-benzyl-idenechroman-4-one, C 16 H 12 O 2, V, and (E)-3-(4-meth-oxy-benzyl-idene)chroman-4-one, C 17 H 14 O 3, VI. The cytotoxic activities of the presented crystal structures have been determined, together with their inter-molecular inter-action preferences and Hirshfeld surface characteristics. An inverse relationship was found between the contribution of C?C close contacts to the Hirshfeld surface and cytotoxic activity against the WM-115 cancer line. Dependence was also observed between the logP value and the percentage contribution of C?H contacts to the Hirshfeld surface.

Full text of DOI:10.1107/S205322962000813X

research papers
The relationship between Hirshfeld potential and
cytotoxic activity: a study along a series of
flavonoid and chromanone derivatives
ISSN 2053-2296
Magdalena Małecka,a* Joachim Kusz,b Lars Eriksson,c Angelika Adamus-Grabickad
.
and Elzbieta Budzisze
Received 13 May 2020
Accepted 18 June 2020
a
´
´
´
´
Department of Physical Chemistry, Faculty of Chemistry, University of Łodz, Pomorska 163/165, 90-236 Łodz, Poland,
bInstitute of Physics, University of Silesia, Uniwersytecka 4, 40-007 Katowice, Poland, cDepartment of Materials and
Environmental Chemistry, Stockholm University, SE-10691 Stockholm, Sweden, dFood Science Department, Faculty of
Pharmacy, Medical University of Łodz, Muszynskiego 1, 90-151 Łodz, Poland, and eDepartment of Cosmetic Raw
Edited by D. S. Yufit, University of Durham,
United Kingdom
´
´
´
´
´
´
´
´
Materials Chemistry, Faculty of Pharmacy, Medical University of Łodz, Muszynskiego 1, 90-151 Łodz, Poland.
*Correspondence e-mail: magdalena.malecka@chemia.uni.lodz.pl
Keywords: chromanone; flavanoid; cytotoxic
activity; Hirshfeld analysis; crystal structure;
QSAR.
The present study examines a series of six biologically-active flavonoid and
chromanone derivatives by X-ray crystal structure analysis: (E)-3-benzylidene-
2-phenylchroman-4-one, C22H16O2, I, (E)-3-(4-methylbenzylidene)-2-phenyl-
chroman-4-one, C23H18O2, II, (E)-3-(3-methylbenzylidene)-2-phenylchroman-4-
one, C23H18O2, III, (E)-3-(4-methoxybenzylidene)-2-phenylchroman-4-one,
C23H18O3, IV, (E)-3-benzylidenechroman-4-one, C16H12O2, V, and (E)-3-(4-
methoxybenzylidene)chroman-4-one, C17H14O3, VI. The cytotoxic activities of
the presented crystal structures have been determined, together with their
intermolecular interaction preferences and Hirshfeld surface characteristics. An
inverse relationship was found between the contribution of CÁ Á ÁC close contacts
to the Hirshfeld surface and cytotoxic activity against the WM-115 cancer line.
Dependence was also observed between the logP value and the percentage
contribution of CÁ Á ÁH contacts to the Hirshfeld surface.
CCDC references: 2010679; 2010678;
2010677; 2010676; 2010675; 2010674
Supporting information: this article has
supporting information at journals.iucr.org/c
1. Introduction
A number of our previous studies have focused on the
synthesis and biological activity of chromone derivatives and
flavonoids (Budzisz et al., 2017; Kupcewicz et al., 2016). These
heterocyclic compounds include a number of plant secondary
metabolites that are widely distributed in nature (Panche et al.,
2016). Although flavonoid compounds can be extracted from
the fruits, roots and leaves of plants, they are also commonly
found in beverages such as wine and tea (Landrault et al.,
2001). Flavonoid compounds, and their derivatives, demon-
strate a wide spectrum of biological activity on plants and
human health (Harborne & Williams, 2000). They protect
plants against biotic stress, act as UV filters and fulfill signaling
and defense functions (Panche et al., 2016); in addition, agly-
cones, glycosides and methylated derivatives are known to
possess a range of antioxidant (Soobrattee et al., 2005), anti-
inflammatory (Serafini et al., 2010), anticancer (Ravishankar et
al., 2013) and antimutagenic properties, and are believed to be
capable of modulating the function of cellular enzymes (Es-
Safi et al., 2007). The present study presents a series of new
flavonoids or chromanones which exhibit promising cytotoxic
activity. The compounds are (E)-3-benzylidene-2-phenylchro-
man-4-one, I, (E)-3-(4-methylbenzylidene)-2-phenylchroman-
4-one, II, (E)-3-(3-methylbenzylidene)-2-phenylchroman-4-one,
III, (E)-3-(4-methoxybenzylidene)-2-phenylchroman-4-one, IV,
# 2020 International Union of Crystallography
Acta Cryst. (2020). C76
https://doi.org/10.1107/S205322962000813X 1 of 11

research papers
Table 1
Experimental details.
Experiments were carried out at 100 K. Absorption was corrected for by multi-scan methods, using CrysAlis PRO (Rigaku OD, 2015) for compounds I–V and
CrysAlis PRO (Rigaku OD, 2019) for compound VI. H-atom parameters were constrained.
I
II
III
Crystal data
Chemical formula
Mr
Crystal system, space group
C22H16O2
312.35
C23H18O2
326.37
Monoclinic, P21/c
16.6799 (5), 7.9102 (2), 13.1511 (3)
C23H18O2
326.37
Triclinic, P1
8.9094 (3), 9.6578 (3), 10.9044 (4)
Monoclinic, C2/c
10.2487 (3), 16.3033 (4),
19.7539 (7)
90, 100.420 (3), 90
3246.20 (17)
8
Mo Kꢀ
0.08
0.28 Â 0.26 Â 0.08
˚
a, b, c (A)
ꢀ, ꢁ, ꢂ (ꢁ)
90, 98.558 (3), 90
1715.85 (8)
4
Mo Kꢀ
0.08
104.378 (3), 109.425 (3), 91.902 (3)
850.24 (5)
2
Mo Kꢀ
0.08
0.28 Â 0.1 Â 0.08
3
˚
V (A )
Z
Radiation type
ꢃ (mmÀ1
Crystal size (mm)
)
0.28 Â 0.1 Â 0.1
Data collection
Diffractometer
Rigaku OD SuperNova Dual
source diffractometer with an
Atlas detector
Rigaku OD SuperNova Dual
source diffractometer with an
Atlas detector
Rigaku OD SuperNova Dual
source diffractometer with an
Atlas detector
Tmin, Tmax
0.744, 1.000
13340, 13340, 11168
0.833, 1.000
13962, 3550, 2927
0.736, 1.000
7284, 3509, 2999
No. of measured, independent and
observed [I > 2ꢄ(I)] reflections
Rint
0.042
0.628
0.031
0.628
0.021
0.628
À1
˚
(sin ꢅ/ꢆ)max (A
)
Refinement
R[F2 > 2ꢄ(F2)], wR(F2), S
No. of reflections
No. of parameters
0.060, 0.153, 1.02
13340
205
0.49, À0.38
0.040, 0.107, 1.05
3550
227
0.19, À0.23
0.037, 0.098, 1.04
3509
227
0.24, À0.21
À3
˚
Áꢇmax, Áꢇmin (e A
)
IV
V
VI
Crystal data
Chemical formula
Mr
C23H18O3
342.37
C16H12O2
236.26
C17H14O3
266.28
Crystal system, space group
˚
Monoclinic, P21/n
23.4111 (3), 8.0027 (1), 28.1094 (5)
90, 97.156 (1), 90
5225.33 (13)
12
Cu Kꢀ
0.69
0.28 Â 0.1 Â 0.08
Triclinic, P1
7.7718 (3), 8.6069 (3), 9.0857 (3)
89.744 (3), 84.862 (3), 74.199 (3)
582.31 (4)
Triclinic, P1
7.5570 (3), 12.3558 (4), 14.4044 (6)
82.748 (3), 87.126 (3), 75.768 (3)
1293.02 (9)
a, b, c (A)
ꢀ, ꢁ, ꢂ (ꢁ)
3
˚
V (A )
Z
Radiation type
2
4
Mo Kꢀ
0.09
0.18 Â 0.08 Â 0.08
Cu Kꢀ
0.76
0.3 Â 0.08 Â 0.06
ꢃ (mmÀ1
Crystal size (mm)
)
Data collection
Diffractometer
Rigaku OD SuperNova Dual
source diffractometer with an
Atlas detector
Rigaku OD SuperNova Dual
source diffractometer with an
Atlas detector
XtaLAB Synergy Dualflex HyPix
Tmin, Tmax
0.997, 1.000
15971, 9323, 7742
0.865, 1.000
4947, 2425, 2120
0.671, 1.000
5118, 5118, 4669
No. of measured, independent and
observed [I > 2ꢄ(I)] reflections
Rint
0.022
0.599
0.023
0.628
0.020
0.595
À1
˚
(sin ꢅ/ꢆ)max (A
)
Refinement
R[F2 > 2ꢄ(F2)], wR(F2), S
No. of reflections
No. of parameters
0.038, 0.104, 1.01
9323
706
0.20, À0.21
0.040, 0.115, 1.06
2425
163
0.29, À0.22
0.070, 0.200, 1.09
5118
364
À3
˚
Áꢇmax, Áꢇmin (e A
)
0.63, À0.33
Computer programs: CrysAlis PRO (Rigaku OD, 2015, 2019), SHELXT (Sheldrick, 2015a), DIAMOND (Brandenburg & Putz, 1999), SHELXL2014 (Sheldrick, 2015b) and publCIF
(Westrip, 2010).
(E)-3-benzylidenechroman-4-one, V, and (E)-3-(4-methoxy-
benzylidene)chroman-4-one, VI (see Scheme 1).
Quantitative structure–activity relationships (QSAR),
being mathematical representations of biological activity, are
widely used to predict the pharmaceutical properties of
potential drug candidates, in particular their cytotoxicity (Roy
et al., 2015). In many cases, the pharmacological effects of
drugs are determined by their interactions between the com-
ꢀ
2 of 11 Małecka et al. A series of flavonoid and chromanone derivatives
Acta Cryst. (2020). C76

research papers
Table 2
Hydrogen-bond geometry (A, ) for compounds I–VI.
pound and the active site of other molecules; such interactions
may be hydrogen bonds, electrostatic forces or van der Waals
interactions (Zheng et al., 2014; Deschamps, 2010). A vast
number of molecular descriptors have their origin in X-ray
crystallography (Cachau & Podjarny, 2005; Deschamps &
George, 2003; Williams et al., 2005). Most of these, such as
hardness (ꢈ) and softness (ꢄ), chemical potential (ꢃ) and
electrophilicity index (!) are available from molecular
modelling. However, the key role in pharmacology and
structure-based drug design is arguably played by information
about molecular structure and intermolecular interactions.
ꢁ
˚
For I, Cg2 is the centroid of the C5–C10 ring and Cg4 of the C18–C23 ring; for
III, Cg4 is the centroid of the C21–C26 ring; for IV, Cg3 is the centroid of the
C11–C16 ring, Cg4 of the C18–C23 ring, Cg8 of the C41–C46 ring, Cg9 of the
C48–C53 ring and Cg13 of the C71–C76 ring.
D—HÁ Á ÁA
D—H
HÁ Á ÁA
DÁ Á ÁA
D—HÁ Á ÁA
Compound I
C11—H11Á Á ÁO4i
C17—H17Á Á ÁO4i
C21—H21Á Á ÁO4ii
C6—H6Á Á ÁCg4iii
C15—H15Á Á ÁCg4iv
C16—H16Á Á ÁCg2iv
0.95
0.95
0.95
0.95
0.95
0.95
2.47
2.64
2.68
2.83
2.89
2.84
3.353 (3)
3.353 (2)
3.267 (3)
3.736 (2)
3.730 (2)
3.539 (2)
154
132
120
160
148
131
Compound II
C2—H2Á Á ÁO4v
C5—H5Á Á ÁO1vi
C24—H24Á Á ÁO4vii
1.00
0.95
0.95
2.27
2.54
2.71
3.174 (2)
3.408 (2)
3.487 (2)
149
152
140
Compound III
C11—H11Á Á ÁO4viii
C17—H17Á Á ÁO4viii
C24—H24Á Á ÁO4ix
C6—H6Á Á ÁCg4x
0.95
0.95
0.95
0.95
2.54
2.69
2.60
2.52
3.3635 (14)
3.5025 (15)
3.2731 (15)
3.4654 (15)
145
144
128
174
Compound IV
C2—H2Á Á ÁO34xi
1.00
0.95
0.95
1.00
0.95
0.95
1.00
0.95
0.95
0.95
0.98
0.98
0.95
0.95
0.98
0.95
0.98
0.98
2.45
2.40
2.46
2.37
2.42
2.42
2.48
2.48
2.49
2.97
2.71
2.91
2.99
2.98
2.75
2.72
2.99
2.90
3.3434 (15)
3.2676 (16)
3.3750 (15)
3.2348 (15)
3.2733 (15)
3.3399 (16)
3.3629 (15)
3.3725 (15)
3.4018 (15)
3.7215915)
3.6762 (15)
3.6005 (17)
3.6985 (14)
3.7434 (15)
3.6774 (15)
3.5324 (15)
3.6203 (16)
3.8631 (15)
148
151
161
144
150
162
146
157
161
136
169
128
133
138
158
144
123
167
C6—H6Á Á ÁO61xii
C14—H14Á Á ÁO1xiii
C32—H32Á Á ÁO64xiv
C36—H36Á Á ÁO1xv
C44—H44Á Á ÁO31xiii
C62—H62Á Á ÁO4xvi
C66—H66Á Á ÁO31xvii
C74—H74Á Á ÁO61xiii
C7—H7Á Á ÁCg8xviii
C211—H21BÁ Á ÁCg4xviii
C211—H21CÁ Á ÁCg3xix
C23—H23Á Á ÁCg9xx
C37—H37Á Á ÁCg3xxi
C511—H51BÁ Á ÁCg13xvi
C53—H53Á Á ÁCg4xxii
C811—H81AÁ Á ÁCg9xii
C811—H81BÁ Á ÁCg8xvi
Flavonoid and chromanone derivatives I–VI were synthe-
sized (Scheme 2) and their cytotoxic activities and crystal
structures determined. The aim of the present study was to
find the relationship between the cytotoxicity of the tested
compounds and the geometric parameters of their crystal
structures, as well as obtaining information by Hirshfeld
surface analysis, as encouraged by previous research (Kupce-
wicz et al., 2016).
Compound V
C7—H7Á Á ÁO4xxiii
C11—H11Á Á ÁO4xxiv
C17—H17Á Á ÁO4 xxiv
0.95
0.95
0.95
2.69
2.56
2.56
3.6131 (16)
3.4153 (15)
3.4050 (16)
166
150
148
Compound VI
C2—H2AÁ Á ÁO22
0.99
0.99
0.95
0.95
0.95
0.95
0.95
0.95
0.95
0.95
2.51
2.58
2.55
2.54
2.45
2.55
2.45
2.46
2.79
2.74
3.430 (3)
3.215 (3)
3.319 (3)
3.196 (3)
3.349 (3)
3.275 (3)
3.381 (3)
3.330 (3)
3.632 (3)
3.573(30
154
122
138
127
157
133
166
153
149
147
C2—H2BÁ Á ÁO1xxv
C5—H5Á Á ÁO2xxvi
2. Experimental
C14—H14Á Á ÁO24xxvii
C17—H17Á Á ÁO1xxviii
C25—H25Á Á ÁO22xxvi
C33—H33Á Á ÁO4xxix
C37—H37Á Á ÁO21xxviii
C8—H8Á Á ÁCg3xxix
C28—H28Á Á ÁCg7xxx
2.1. Synthesis and crystallization
The general method for the synthesis of (E)-3-benzylidene-
4-chromanone and the flavanone derivatives consists of the
condensation of 4-chromanone or flavanone with the appro-
priate aromatic aldehyde in the presence of piperidine as a
catalyst (Scheme 2). The use of excess catalyst may result in
the transition of an exo–endo double bond between the C3
and C4 atoms in the flavanone ring, resulting in the production
of 3-benzyl-2-phenylchromen-4-one derivatives (Levai, 2004).
Compounds I–IV were synthesized according to Pijewska et al.
(1993), and compounds V and VI according to Levai & Schag
(1979). Both syntheses were slightly modified by Adamus-
Grabicka et al. (2020). Analytical data for compounds I–VI are
given in the supporting information. Single crystals suitable
Symmetry codes: (i) Àx, y, Àz + 21; (ii) Àx + 21, y À , Àz + 12; (iii) x À , y À , z; (iv) x + 1, y,
1
2
1
1
2
2
1
1
z; (v) x, Ày + 32, z À ; (vi) x, Ày + 32, z + 12; (vii) x, Ày + 12, z À ; (viii) Àx + 1, Ày, Àz + 1; (ix)
2
2
Àx + 1, Ày, Àz; (x) x À 1, y, z; (xi) Àx + 12, y + 21, Àz + 23; (xii) Àx + 12, y + 21, Àz + 12; (xiii) x,
y + 1, z; (xiv) x + 12, Ày + 21, z + 21; (xv) Àx + 12, y À , Àz + 32; (xvi) Àx + 21, y À , Àz + 12; (xvii)
1
1
2
2
1
1
1
2
1
1
2
x À , Ày + 12, z À , (xviii) Àx À , Ày + 32, z À ; (xix) Àx + 21, y À , Àz + 32; (xx) x, y, z; (xxi)
2
2
2
x + 12, Ày + 32, z + 21; (xxii) x, y À 1, z; (xxiii) x, y + 1, z; (xxiv) Àx + 1, Ày + 1, Àz + 2; (xxv)
Àx + 1, Ày + 3, Àz + 1; (xxvi) x, y À 1, z; (xxvii) x, y + 1, z; (xxviii) x + 1, y, z; (xxix) x À 1,
y, z; (xxix) Àx + 1, Ày + 3, Àz + 1; (xxx) Àx, Ày + 2, Àz + 2.
for X-ray diffraction studies were obtained from ethanol or
methanol solution by slow evaporation at room temperature.
ꢀ
Acta Cryst. (2020). C76
Małecka et al.
A series of flavonoid and chromanone derivatives 3 of 11

research papers
2.2. Refinement
0.00 1.00. The twin law to convert hkl from the first to this
domain (SHELXL TWIN matrix) was À1.0003 0.0011
À0.0003 À0.0024 À0.9995 À0.0002 À0.0728 À0.2831 1.0003.
Crystal data, data collection and structure refinement
details are summarized in Table 1. All H atoms were fixed at
calculated positions and refined in riding mode, with C—H =
˚
0.95, 0.98, 0.99 and 1.00 A for aromatic, methyl, methylene and
3. Results and discussion
methine H atoms, and with Uiso(H) = 1.2Ueq(C) for aromatic,
methylene and methane H atoms, and Uiso(H) = 1.5Ueq(C) for
methyl H atoms.
The structure of IV has three independent molecules in the
asymmetric unit, and that of VI has two molecules in the
asymmetric unit. The structure of VI was refined as a rota-
tional twin rotated from the first domain by À179.9192ꢁ about
the reciprocal axis [À0.04 À0.14 0.99] and the real axis 0.00
3.1. Molecular structures of compounds I–VI
The molecular structures of compounds I–VI are shown in
Fig. 1. Compound IV crystalizes with three molecules in the
asymmetric unit, while compound VI crystallizes with two
molecules in the asymmetric unit. The main body of the
presented structures consists of a chroman-4-one skeleton, i.e.
an arene ring fused with a tetrahydropyran-4-one ring. Posi-
Figure 1
Views of the molecular structures of compounds I–VI with the atom-numbering schemes. Displacement ellipsoids are drawn at the 50% probability level.
ꢀ
4 of 11 Małecka et al. A series of flavonoid and chromanone derivatives
Acta Cryst. (2020). C76

research papers
Figure 2
(a) Packing of compound I showing the C11—H11Á Á ÁO4i and C17—H17Á Á ÁO4i hydrogen-bonded dimers. (b) A fragment of the molecular structure with
two chains forming a hydrogen bond via C21—H21Á Á ÁO4ii (violet) hydrogen bonds, with the C11—H11Á Á ÁO4i and C17—H17Á Á ÁO4i hydrogen bonds
drawn in blue. Generic atom labels without symmetry codes have been used.
tion 3 of the chroman moiety is connected to a benzylidene (in
I), 4-methylbenzylidene (in II), 3-methylbenzylidene (in III),
4-methoxybenzylidene (in IV), benzylidene (in V) or
4-methoxybenzylidene (in VI) substituent. For all six struc-
tures, these substituents are rotated with respect to the
chroman moiety, as reflected in their corresponding dihedral
angles of 46.8 (2), 37.7 (2), 67.4 (2), 33.8 (2)–36.4 (2) (three
molecules in the asymmetric unit), 54.9 (2) and 56.4 (2)–
58.6 (2)ꢁ (two molecules in the asymmetric unit), respectively.
In structures I–IV, the chroman moiety is substituted at
position 2 by a phenyl ring, which is nearly perpendicular to
plane of the main chroman skeleton, with the dihedral angles
of 85.6 (2), 89.4 (2), 89.3 (2) and 86.9 (2)–88.2 (2)ꢁ, respec-
tively. Compounds whose substituents at position C2 are more
perpendicular with respect to the chroman moiety also have
benzylidene substituents at position 3 that are more parallel
(Table S1 in the supporting information). The pyran rings
adopt mainly envelope (E) or screw-boat (S) conformations,
with asymmetry parameters in the range ÁCs(C2) = 1.6 (2)–
10.5 (3)ꢁ (Duax & Norton, 1975) for IVA, V and VIB, and
ÁC2(O1—C2) = 7.9 (2)–13.0 (2)ꢁ (Duax & Norton, 1975) for
II, IVB, IVC and VIA (suffixes A–C denotes molecules A–C).
These conformations are confirmed by the respective puck-
ering parameters (Cremer & Pople, 1975), i.e. Q = 0.337 (2)–
ꢁ
ꢁ
˚
0.446 (2) A, ꢅ = 59.4 (2)–120.9 (2) and ’ = 43.6 (2)–233.7 (4) .
Details of the puckering parameters are given in Table S2 of
the supporting information.
3.2. Crystal structure analysis
The solid-state structures of compounds I–VI display a
combination of C—HÁ Á ÁO, C—HÁ Á Áꢉ and very weak ꢉ–ꢉ
interactions (see Table 2 for geometric parameters and
symmetry codes). In I, atoms C11 and C17 act as donors in C—
HÁ Á ÁO hydrogen bonds with atom O4i as acceptor, forming a
dimer. The C21 atom acts as a donor to O21ii as acceptor
Figure 4
The crystal structure of compound II, showing C2—H2Á Á ÁO4v, C5—
H5Á Á ÁO1vi and C24—H24Á Á ÁO4vii hydrogen bonds. Generic atom labels
without symmetry codes have been used.
Figure 5
Figure 3
Fragment of the crystal structure of compound III showing the double
chains formed by two dimers. One dimer is created by C11—H11Á Á ÁO4viii
and C17—H17Á Á ÁO4 viii hydrogen bonds, while the second is produced by
the C24—H24Á Á ÁO4ix hydrogen bond. Generic atom labels without
symmetry codes have been used.
Fragment of the crystal packing of compound I, showing C6—H6Á Á ÁCg4iii,
C15—H15Á Á ÁCg4iv and C16—H16Á Á ÁCg2iv interactions. Cg4 is a centroid
of the C18–C23 ring (red dot) and Cg2 is the centroid of the C5–C10 ring
(yellow dot). See Table 2 for symmetry codes.
ꢀ
Acta Cryst. (2020). C76
Małecka et al.
A series of flavonoid and chromanone derivatives 5 of 11

research papers
Figure 6
Fragment of the crystal packing of compound III, showing (a) C6—H6Á Á ÁCg4x and (b) ꢉ–ꢉ interactions between rings 3 (atoms C12–C17). Cg4 is the
centroid of the C21–C26 ring (red dot) and the centroid of ring 3 is shown as a green dot.
(Fig. 2). This interaction generates a double chain along the
[001] direction. C—HÁ Á Áꢉ interactions are also observed in the
crystal packing. They are formed by C6—H6Á Á ÁCg4iii, C15—
H15Á Á ÁCg4iv and C16—H16Á Á ÁCg2iv (Fig. 3).
between arene rings substituted at the C3 atom of the
chroman moiety, the distance between the centroids
˚
(Cg3Á Á ÁCg3) being 3.854 (2) A. Another weak interaction is
C6—H6Á Á ÁCg4x (Fig. 6).
In the case of the crystal packing of compound II, molecules
are linked via two hydrogen bonds, i.e. C2—H2Á Á ÁO4v and
C5—H5Á Á ÁO1vi, forming chains along the [010] direction. In
addition, these chains are connected via C24—H24Á Á ÁO4vii
hydrogen bonds (Fig. 4).
Compound IV crystallizes in the space group P21/n with an
asymmetric unit comprising three independent molecules;
these are self-assembled into chains along the [101] direction,
and are always connected by two hydrogen bonds from each
molecule, i.e. C2—H2Á Á ÁO34xi and C6—H6Á Á ÁO61xii in mol-
ecule A, C32—H32Á Á ÁO64xiv and C36-H36Á Á ÁO1xv in molecule
B, and C62—H62Á Á ÁO4xvi and C66—H66Á Á ÁO31xvii in mol-
ecule C. Each chain combines with another similarly formed
chain via C14—H14Á Á ÁO1xiii, C44—H44Á Á ÁO31xiii and C74—
H74Á Á ÁO61xiii hydrogen bonds shifted by a b translation. C—
HÁ Á Áꢉ interactions are also evident in the crystal structure of
IV (Table 2). The shortest centroid–centroid distance
The crystal packing of III seems to be stabilized by a
combination of intermolecular C—HÁ Á ÁO and C—HÁ Á Áꢉ
hydrogen bonds and ꢉ–ꢉ stacking interactions. The C11 and
C17 atoms act as donors to the O4viii atom, forming dimers.
The other dimer is formed by the C24—H24Á Á ÁO4ix hydrogen
bond. However, the three hydrogen bonds given above form
double chains propagating along the [100] direction (Fig. 5).
The crystal lattice also demonstrates a weak ꢉ–ꢉ interaction
˚
(Cg2Á Á ÁCg7) of 3.9671 (8) A was found between parallel arene
Figure 7
Fragment of the crystal structure of compound IV, showing two chains formed between three independent molecules via C2—H2Á Á ÁO34xi and C6—
H6Á Á ÁO61xii hydrogen bonds for molecule A, C32—H32Á Á ÁO64xiv and C36—H36Á Á ÁO1xv for molecule B, and C62—H62Á Á ÁO4xii and C66—H66Á Á ÁO31xvi
for molecule C, linked by C14—H14Á Á ÁO1xiii, C44—H44Á Á ÁO31xiii and C74—H74Á Á ÁO61xiii hydrogen bonds. Generic atom labels without symmetry codes
have been used.
ꢀ
6 of 11 Małecka et al. A series of flavonoid and chromanone derivatives
Acta Cryst. (2020). C76

research papers
Figure 8
Fragment of the crystal packing of structure V, with C7—H7Á Á ÁO4xxiii hydrogen bonds (blue line) forming chains, and C11—H11Á Á ÁO4xxiv and C17—
H17Á Á ÁO4xxiv hydrogen bonds (violet line) forming dimers. Generic atom labels without symmetry codes have been used.
3.3. Determination of lipophilicity
rings (fused with the pyran ring) of molecules A and B;
however, it seems that ꢉ–ꢉ interactions do not play a signifi-
cant role in the crystal packing (Fig. 7).
One of the key determinants influencing the bioavailability,
permeability and toxicity of a potential drug is its lipophilicity
In the packing structure of V, the molecules are connected
via a C7—H7Á Á ÁO4xxiii hydrogen bond, forming chains along
the [010] direction, while each molecule is also engaged in
creating a dimer by a combination of C17—H17Á Á ÁO4xxiv and
C11—H11Á Á ÁO4xxiv hydrogen bonds (Fig. 8). These inter-
actions are also enhanced by ꢉ–ꢉ interactions between arene
rings (ring 2) fused with pyran rings, with the Cg2Á Á ÁCg2
´ ´
(Jozwiak et al., 2001). Lipophilicity is affected by the structure
of the molecule, as well as the presence of functional groups,
unsaturated bonds and the molecular weight. It is usually
defined as the partition coefficient between the organic and
aqueous phases (n-octanol/water) and is designated as logP
(Gao & Cao, 2008; Kujawski et al., 2012). The logP factor is an
important variable used in computer-based drug design, and a
number of computational logP prediction tools have been
designed, such as the Molinspiration Cheminformatics soft-
ware package (https://www.molinspiration.com/). Unfortu-
nately, theoretical methods do not always give results
consistent with the experimental results, because they do not
take into account the intermolecular interactions taking place
in the reaction environment.
Therefore, in the present study, the theoretical lipophilicity
values obtained using the Molinspiration Cheminformatics
program (miLogP) were compared with experimental values,
determined using reversed-phase thin-layer chromatography
(RP-TLC) (Table 3). The experimental method for deter-
mining lipophilicity is described in the supporting information.
The logP results indicate that the tested compounds have a
lipophilic character. As the logP parameters for compounds I
and IV–VI are given in a previous work (Adamus-Grabicka et
al., 2020), the present article only discusses the results for
compounds II and III. Briefly, it was found that compound II is
characterized by greater lipophilicity than compound III,
probably due to the presence of a methyl group in the para
˚
distance equal to 3.770 (2) A (Fig. 9).
Compound VI crystallizes in the triclinic space group P1
with two independent molecules in the asymmetric unit. In the
crystal structure, two independent molecules are linked by a
C2—H2AÁ Á ÁO22 hydrogen bond. The remaining seven
hydrogen bonds (Table 2) create a three-dimensional (3D) net
of hydrogen bonds (Fig. 10). In the crystal lattice of VI,
aromatic ꢉ–ꢉ interactions are also observed between the
arene ring (ring 2) fused with the pyran rings and another
arene ring incorporating methoxyphenyl substituents (Fig. 11).
Table 3
The experimental (exp) and theoretical (theor) values of lipophilicity.
Compound
logP(exp )
milogP(theor)
I
II
III
IV
V
4.90
4.45
3.05
4.79
4.23
4.08
5.20
5.65
5.63
5.26
3.62
3.68
Figure 9
Fragment of the crystal packing of compound V, showing ꢉ–ꢉ interactions
between rings 2 (atoms C5–C10).
VI
ꢀ
Acta Cryst. (2020). C76
Małecka et al.
A series of flavonoid and chromanone derivatives 7 of 11

research papers
Figure 10
Fragment of the crystal packing of VI, demonstrating the hydrogen bond (i.e. C2—H2AÁ Á ÁO22) present between two independent molecules and the 3D
net of other hydrogen bonds. Generic atom labels without symmetry codes have been used.
position on the arene ring. Usually, the location of the methyl
group in the meta position causes a decrease in the logP value
(Fujita et al., 1964).
All the tested compounds show high lipophilicity and high
bioaccumulation potential. They also satisfy the ‘rule of five’
for drug-like molecules described by Lipinski et al. (2001).
Therefore, based on the results of the lipophilicity test and
Lipinski’s rule, it can be assumed that the tested compounds
may be good candidates for further research as potential
drugs.
(2020). Compound III exhibits similar cytotoxic activity
towards all tested cell lines, although the best cytotoxic activity
was observed against COLO-205 (32.64 mM). It demonstrates
slightly lower activity (48.81 mM) against HL-60 than com-
pound II, where the methyl group is in the para position.
Compound III also shows better antiproliferative character
towards the other three cell lines.
Comparing the tested compounds, the best cytotoxic
activity was demonstrated by compound V, i.e. an unsub-
stituted 3-arylidenechromanone, especially towards the leuk-
emia cell lines (HL-60 and NALM-6) (Fig. 12). All tested
compounds show different levels of cytotoxic activity ranging
from high (5.4 Æ 0.6 mM) to virtually no activity (>250 mM);
however, compound Vappeared to be the best cytotoxic agent
against all four cancer cell lines, as well as towards reference
compounds. In addition, all compounds demonstrated a
3.4. Biological assay
The title compounds were tested for cytotoxicity by the
MTTassay against four cell lines: HL-60 (human leukemia cell
line), NALM-6 (human peripheral blood leukemia cell line),
WM-115 (melanoma cell line, ECACC, Salisbury, UK) and
COLO-205 (human colon adenocarcinoma cells). The proce-
dure is given in the supporting information. The results are
presented as a logarithmic function in Fig. 12 and as the
inhibitory concentration (IC50) in ꢃM in Table S3 in the
supporting information.
1
logarithmic dependence of IC towards leukemia cell lines. It is
50
worth mentioning that the compounds demonstrating greater
toxicity to the HL-60 line also demonstrated greater toxicity to
the NALM-6 line (Fig. S1 in the supporting information).
The effect of the synthesized and reference compounds on
erythrocyte hemolysis was also investigated. Neither com-
pound II nor III was found to have any unfavourable effect on
the erythrocyte membrane over the whole tested concentra-
tion range. In addition, erythrocyte morphology was also
The biological activity of benzylidene flavanone/chroma-
none derivatives and the cytotoxic activities of compounds I,
IV, Vand VI are discussed in detail by Adamus-Grabicka et al.
Figure 11
Fragment of the crystal packing lattice of VI, showing ꢉ–ꢉ interactions. The yellow dots indicate the centroids of the C5–C10 (molecule A) and C25–C30
(molecule B) rings, while the green dots indicate the centroids of the C12–C17 (molecule A) and C32–C37 (molecule B) rings.
ꢀ
8 of 11 Małecka et al. A series of flavonoid and chromanone derivatives
Acta Cryst. (2020). C76

research papers
In addition, 2D fingerprint plots are given, and these are
decomposed into fractions to provide quantitative information
regarding individual interactions (Fig. S2 in the supporting
information). These figures also include the percentage
contribution of the particular contact in the overall Hirshfeld
surface (Fig. 13). Although the 2D fingerprint plots differ
between compounds I–VI, distinctive common features can be
identified. The C—HÁ Á Áꢉ interactions observed in the crystal
structures of I, III, IV and VI occur as ‘chicken-wing’ shapes
on two sides of the fingerprint plots. Additionally, the parti-
cipation of ꢉ–ꢉ interactions in the crystal structures of III, V
and VI shows up as a light-blue region near the centre of the
plot.
The relative contribution of the different interactions to the
Hirshfeld surface is presented as a histogram in Fig. 13. From
this comparison, it can be clearly seen that hydrogen-bonding
interactions (C—HÁ Á ÁO and C—HÁ Á Áꢉ) cover nearly 50% of
the surface area, where CÁ Á ÁH contacts dominate. Less than
10% of the surface can be associated with CÁ Á ÁC contacts,
often referred to as ꢉ–ꢉ interactions. The dominant inter-
action in all the derivatives is the HÁ Á ÁH interaction, consti-
tuting 43–54% of all interactions.
3.5.1. CÁ Á ÁC contacts contribution versus cytotoxic activity
and lipophilicity. Simple correlations were found between the
results of the Hirshfeld surface analysis and the cytotoxicity
values for these compounds. The cytotoxic activity of all the
compounds against WM-115 (melanoma cell line) is inversely
proportional to the percentage contribution of CÁ Á ÁC contacts
to the Hirshfeld surface (Fig. 14). This indicates that the
activity of these compounds is strongly influenced by inter-
molecular interactions.
A comparison of the logP value (theoretical) with the con-
tribution of various contacts to the Hirshfeld surface found
that theoretical lipophilicity (logP) is also inversely propor-
tional to the percentage contribution of the CÁ Á ÁC contacts to
the Hirshfeld surface. This analysis has been extended by
similar flavonoid compounds and benzylidenochromanone
derivatives available from our previous research (Kupcewicz
et al., 2013; Adamus-Grabicka et al., 2018; Suchojad et al.,
Figure 12
The cytotoxic activity (expressed as logIC ) against the HL-60, NALM-6,
1
50
WM-115 and COLO-205 cancer cell lines.
examined as a complement to the erythrotoxicity studies; the
methodology and results of the RBC lysis and morphology
tests are described in Adamus-Grabicka et al. (2020). None of
the tested compounds was found to be toxic towards red blood
cells at cytotoxic concentrations, and none contributed to
RBC hemolysis.
3.5. Hirshfeld surface
The Hirshfeld surfaces (Hirshfeld, 1977; Spackman &
Jayatilaka, 2009) of the crystal structures of compounds I–VI
were determined using the CrystalExplorer program (Turner
et al., 2017). Hirshfeld surface analysis is an efficient method
for identifying intermolecular interactions in the solid state
and mapping their properties in useful modes, such as
normalized contact distance (dnorm) surface, curvedness
surface, shape index and two-dimensional (2D) fingerprints
(McKinnon et al., 2007). The Hirshfeld surfaces mapped over
dnorm are presented in Fig. S2 in the supporting information;
this figure presents the similarities and differences in the
crystal structures between compounds I–VI. The vivid red
spots present contacts which correspond to the interactions
described above (Fig. S2 in the supporting information, and
Table 2).
Figure 14
The relationship between cytotoxic activity (given as logIC ) and the
1
Figure 13
The percentage contributions to the Hirshfeld surface area of different
close intermolecular contacts for molecules I–VI.
percentage contribution to the Hirshfeld surface covered50 by CÁ Á ÁC
contacts against cell line WM115.
ꢀ
Acta Cryst. (2020). C76
Małecka et al.
A series of flavonoid and chromanone derivatives 9 of 11

research papers
Figure 15
The relationship between the logP value (theoretical) and the fraction of CÁ Á ÁC (red triangles) and CÁ Á ÁH (green dots are flavonoids and blue squares are
chromanones) interactions with respect to the Hirshfeld surface.
2019) or from the Cambridge Structural Database [Version
5.41, last update November 2019; Groom et al., 2016; FAVVIH
(Katrusiak et al., 1987), NAMXIK, NAMXOQ, NAMXUW,-
NAMYEH, NAMYOR, NAMYUX, NAMZEI, NAMZOS,
NAMZUY and NANBAH (Cheng et al., 2011), NANDOB
(Valkonen et al., 2012), SECBAF (Gopaul et al., 2012a),
YAWLEP (Gopaul et al., 2012b) and YEJPIO (Gopaul &
Koorbanally, 2012)]. The scheme used for the search is pre-
sented in Fig. S2 in the supporting information. Disordered
structures were omitted. The total number of analyzed com-
pounds is 7 flavonoids and 19 benzylidenechromanones. For
all compounds, the complete Hirshfeld surface analysis were
carried out with fingerprint plots and contacts contribution to
the Hirshfeld surface (Fig. S3 in the supporting information).
These findings provide a better correlation between the
contributions of CÁ Á ÁC contacts and logP than that reported
previously (Małecka & Budzisz, 2014). However, it can be
seen that the percentage contribution of CÁ Á ÁH contacts in the
Hirshfeld surface also shows an acceptable relationship with
logP separately for flavonoids and for benzylidenechroman-
one derivatives (Fig. 15). These findings clearly indicate that
intermolecular interactions have a strong influence on the
activity of the tested compounds. Therefore, the cytotoxic
activity of a potential drug, and some of its other descriptors,
such as logP, can be successfully predicted based on the
fraction of contacts contributing to the Hirshfeld surface.
These findings support our latest QSAR model (Kupcewicz et
al., 2016) and could help future efforts towards structure-
based drug design.
possible to predict the lipophilicity of a compound on the basis
of X-ray crystallographic data and vice versa. Although these
results were derived from a limited data set, they nevertheless
indicate that quantitative data obtained by Hirshfeld surface
analysis may be valuable in QSAR studies. QSAR models
built on such descriptors become interpretable.
Acknowledgements
The authors would like to thank Dr Jakub Wojciechowski for
technical support during the measurement and integration of
data for compound VI. The authors would like to thank Dr
Magdalena Markowicz-Piasecka for help in the biological
study of the erythrotoxicity of the tested compounds.
Funding information
Funding for this research was provided by: University of Lodz
(grant No. B1811100000050.01 to MM); Medical University of
Lodz (grant No. 502-03/3-066-02/502-34-118 to AAG);
Medical University of Lodz (grant No. 503/3-066-02/503-31-
001 to EB).
References
´
Adamus-Grabicka, A. A., Markowicz-Piasecka, M., Cieslak, M.,
Krolewska-Golinska, K., Hikisz, P., Kusz, J., Małecka, M. &
´
´
Budzisz, E. (2020). Molecules, 25, 1613–1638.
Adamus-Grabicka, A. A., Markowicz-Piasecka, M., Ponczek, M. B.,
Kusz, J., Małecka, M., Krajewska, U. & Budzisz, E. (2018).
Molecules, 23, 3172–3187.
Brandenburg, K. & Putz, H. (1999). DIAMOND. Crystal Impact
GbR, Bonn, Germany.
Budzisz, E., Paneth, P., Geromino, I., Muzioł, T., Rozalski, M.,
Krajewska, U., Pipiak, P., Ponczek, M. B., Małecka, M. &
Kupcewicz, B. (2017). J. Mol. Struct. 1137, 267–276.
Cachau, R. E. & Podjarny, A. D. (2005). J. Mol. Recognit. 18, 196–202.
Cheng, X.-M., Huang, Z.-T. & Zheng, Q.-Y. (2011). Tetrahedron, 67,
9093–9098.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
Deschamps, J. R. (2010). Life Sci. 86, 585–589.
Deschamps, J. R. & George, C. (2003). TrAC Trends Anal. Chem. 22,
561–564.
4. Conclusion
The present study examines the relationship between the
structures of a group of flavonoid and chromanone derivatives
and their cytotoxic activity. An inverse relationship was found
between the percentage contribution of CÁ Á ÁC contacts to the
Hirshfeld surface and cytotoxic activity against the WM-115
cancer line. It was also revealed that the logP value is
dependent upon the percentage contributions of the CÁ Á ÁC
and CÁ Á ÁH contacts to the Hirshfeld surface. In this case, it is
Duax, W. L. & Norton, D. A. (1975). In Atlas of Steroid Structure,
Vol. 1. New York: Plenum Press.
ꢀ
10 of 11 Małecka et al. A series of flavonoid and chromanone derivatives
Acta Cryst. (2020). C76

research papers
Es-Safi, N.-E., Kollmann, A., Khlifi, S. & Ducrot, P.-H. (2007). Food
Sci. Technol. 40, 1246–1252.
Panche, A. N., Diwan, A. D. & Chandra, S. R. (2016). J. Nutrit. Sci.
5(47), 1–15.
Fujita, T., Iwasa, J. & Hansch, C. J. (1964). J. Am. Chem. Soc. 86,
5175–5180.
Pijewska, L., Kamecki, J. & Perka-Karolczak, W. (1993). Pharmazie,
48, 254–257.
Gao, S. & Cao, Ch. (2008). Int. J. Mol. Sci. 6, 962–977.
Gopaul, K. & Koorbanally, N. A. (2012). Private communication
(refcode YEJPIO). CCDC, Cambridge, England.
Gopaul, K., Koorbanally, N. A., Shaikh, M. M., Su, H. &
Ramjugernath, D. (2012a). Acta Cryst. E68, o3062.
Gopaul, K., Shaikh, M., Ramjugernath, D., Koorbanally, N. A. &
Omondi, B. (2012b). Acta Cryst. E68, o1006.
Ravishankar, D., Rajora, A. K., Greco, F. & Osborn, H. M. I. (2013).
Int. J. Biochem. Cell. Biol. 45, 2821–2831.
Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction Ltd,
Yarnton, Oxfordshire, England.
Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction Ltd,
Yarnton, Oxfordshire, England.
Roy, K., Kar, S. & Narayan Das, R. (2015). In Understanding the
Basics of QSAR for Application in Pharmaceutical Sciences and
Risk Assessment. Amsterdam: Elsevier.
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta
Cryst. B72, 171–179.
Harborne, J. B. & Williams, Ch. A. (2000). Phytochemistry, 55, 481–504.
Hirshfeld, F. L. (1977). Theor. Chim. Acta, 44, 129–138.
Serafini, M., Peluso, I. & Raguzzini, A. (2010). Proc. Nutr. Soc. 69,
273–278.
´ ´
´
Jozwiak, K., Szumiło, H. & Soczewinski, E. (2001). Wiad. Chem. 55,
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
Soobrattee, M. A., Neergheen, V. S., Luximon-Ramma, A., Aruoma,
O. I. & Bahorun, T. (2005). Mutat. Res./Fundam. Mol. Mech.
Mutagen. 579, 200–213.
1047–1074.
Katrusiak, A., Ratajczak-Sitarz, M., Kałuski, Z. & Orlov, V. D. (1987).
Acta Cryst. C43, 103–105.
´
Kujawski, J., Popielarska, H., Myka, A., Drabinska, B. & Bernard,
M. K. (2012). Comput. Methods Sci. Technol. 18, 81–88.
Kupcewicz, B., Balcerowska-Czerniak, G., Małecka, M., Paneth, P.,
Krajewska, U. & Rozalski, M. (2013). Bioorg. Med. Chem. Lett. 23,
4102–4106.
Kupcewicz, B., Małecka, M., Zapadka, M., Krajewska, U., Rozalski,
M. & Budzisz, E. (2016). Bioorg. Med. Chem. Lett. 26, 3336–3341.
Landrault, N., Poucheret, P., Ravel, P., Gasc, F., Cros, G. & Teissedre,
P.-L. (2001). J. Agric. Food Chem. 49, 3341–3348.
Levai, A. (2004). Arkivoc, 7, 15–33.
Levai, A. & Schag, J. (1979). Pharmazie, 34, 747–749.
Lipinski, C. A., Lombardo, F. M., Dominy, B. W. & Feeney, P. J.
(2001). Adv. Drug Deliv. Rev. 46, 3–26.
Małecka, M. & Budzisz, E. (2014). CrystEngComm, 16, 6654–6663.
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem.
Commun. pp. 3814–3816.
Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–
32.
Suchojad, K., Dołe˛ga, A., Adamus-Grabicka, A., Budzisz, E. &
Małecka, M. (2019). Acta Cryst. E75, 1907–1913.
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J.,
Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017).
CrystalExplorer17. The University of Western Australia. http://
crystalexplorer.scb.uwa.edu.au/.
´
Valkonen, A., Laihia, K., Kolehmainen, E., Kauppinen, R. & Perjesi,
P. (2012). Struct. Chem. 23, 209–217.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
Williams, S. P., Kuyper, L. F. & Pearce, K. H. (2005). Curr. Opin.
Chem. Biol. 9, 371–380.
Zheng, H., Hou, J., Zimmerman, M. D., Wlodawer, A. & Minor, W.
(2014). Exp. Opin. Drug. Discov. 9, 125–137.
ꢀ
Acta Cryst. (2020). C76
Małecka et al.
A series of flavonoid and chromanone derivatives 11 of 11

supporting information
supporting information
Acta Cryst. (2020). C76 [https://doi.org/10.1107/S205322962000813X]
The relationship between Hirshfeld potential and cytotoxic activity: a study
along a series of flavonoid and chromanone derivatives
Magdalena Małecka, Joachim Kusz, Lars Eriksson, Angelika Adamus-Grabicka and Elżbieta
Budzisz
Computing details
Data collection: CrysAlis PRO (Rigaku OD, 2015) for compound_I_AAG10, compound_II_AAG9,
compound_III_AAG1, compound_V_AAG5; CrysAlis PRO (Agilent, 2013) for compound_IV_AAG2; CrysAlis PRO
(Rigaku OD, 2019) for AAG4. Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for compound_I_AAG10,
compound_II_AAG9, compound_III_AAG1, compound_V_AAG5; CrysAlis PRO (Agilent, 2013) for
compound_IV_AAG2; CrysAlis PRO (Rigaku OD, 2019) for AAG4. Data reduction: CrysAlis PRO (Rigaku OD, 2015)
for compound_I_AAG10, compound_II_AAG9, compound_III_AAG1, compound_V_AAG5; CrysAlis PRO (Agilent,
2013) for compound_IV_AAG2; CrysAlis PRO (Rigaku OD, 2019) for AAG4. For all structures, program(s) used to
solve structure: SHELXS (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b);
molecular graphics: DIAMOND (Brandenburg & Putz, 1999); software used to prepare material for publication:
SHELXL2014 (Sheldrick, 2015b) and publCIF (Westrip, 2010).
(E)-3-Benzylidene-2-phenylchroman-4-one (compound_I_AAG10)
Crystal data
C22H16O2
Mr = 312.35
F(000) = 1312
Dx = 1.278 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 7518 reflections
θ = 3.4–35.7°
Monoclinic, C2/c
a = 10.2487 (3) Å
b = 16.3033 (4) Å
c = 19.7539 (7) Å
β = 100.420 (3)°
V = 3246.20 (17) Å3
Z = 8
µ = 0.08 mm−1
T = 100 K
Plate, colorless
0.28 × 0.26 × 0.08 mm
Data collection
Rigaku OD SuperNova Dual source
diffractometer with an Atlas detector
Radiation source: micro-focus sealed X-ray
tube, SuperNova (Mo) X-ray Source
Mirror monochromator
Tmin = 0.744, Tmax = 1.000
13340 measured reflections
13340 independent reflections
11168 reflections with I > 2σ(I)
R
int = 0.042
Detector resolution: 10.4498 pixels mm-1
ω scans
θmax = 26.5°, θmin = 3.3°
h = −12→9
k = −20→20
l = −24→24
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
Acta Cryst. (2020). C76
sup-1

supporting information
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.060
wR(F2) = 0.153
S = 1.02
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
2
w = 1/[σ2(Fo ) + (0.060P)2 + 1.5246P]
2
where P = (Fo + 2Fc2)/3
13340 reflections
205 parameters
0 restraints
(Δ/σ)max < 0.001
Δρmax = 0.49 e Å−3
Δρmin = −0.38 e Å−3
Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance
matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles;
correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate
(isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refined as a 2-component perfect twin.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
O1
O4
C2
H2
0.32317 (14)
0.17916 (15)
0.2187 (2)
0.1530
0.18634 (9)
0.30418 (10)
0.14416 (13)
0.1238
0.46640 (7)
0.28534 (9)
0.41919 (11)
0.4471
0.0255 (4)
0.0375 (4)
0.0226 (4)
0.027*
C3
C4
C5
H5
0.14523 (19)
0.2246 (2)
0.4459 (2)
0.4200
0.20038 (12)
0.26304 (13)
0.33109 (14)
0.3550
0.36501 (11)
0.33592 (11)
0.34907 (13)
0.3048
0.0220 (4)
0.0248 (5)
0.0320 (5)
0.038*
C6
H6
0.5669 (2)
0.6254
0.35083 (15)
0.3871
0.38841 (14)
0.3709
0.0377 (6)
0.045*
C7
H7
0.6030 (2)
0.6850
0.31731 (14)
0.3325
0.45384 (14)
0.4816
0.0350 (6)
0.042*
C8
H8
0.5213 (2)
0.5471
0.26219 (13)
0.2394
0.47898 (12)
0.5237
0.0288 (5)
0.035*
C9
0.40053 (19)
0.36040 (19)
0.01360 (19)
−0.0155
−0.09296 (11)
−0.07390 (11)
0.0124
−0.18105 (15)
−0.1680
−0.30727 (12)
−0.3805
0.24013 (12)
0.27579 (13)
0.19908 (13)
0.2393
0.14678 (8)
0.06755 (9)
0.0441
0.02267 (8)
−0.0315
0.05701 (10)
0.0263
0.43838 (11)
0.37392 (11)
0.34047 (11)
0.3063
0.35704 (8)
0.38294 (8)
0.3909
0.39717 (9)
0.4149
0.38550 (9)
0.3952
0.0225 (4)
0.0241 (5)
0.0249 (5)
0.030*
0.0276 (5)
0.0342 (6)
0.041*
0.0425 (6)
0.051*
0.0448 (7)
0.054*
C10
C11
H11
C12
C13
H13
C14
H14
C15
H15
C16
H16
C17
H17
−0.32633 (10)
−0.4126
−0.21918 (13)
−0.2322
0.13624 (10)
0.1597
0.18112 (8)
0.2353
0.35960 (8)
0.3516
0.34537 (8)
0.3277
0.0412 (6)
0.049*
0.0334 (5)
0.040*
Acta Cryst. (2020). C76
sup-2

supporting information
C18
C19
H19
C20
H20
C21
H21
C22
H22
C23
H23
0.27922 (18)
0.34181 (19)
0.3452
0.3992 (2)
0.4422
0.3943 (2)
0.4342
0.3308 (2)
0.3261
0.06873 (12)
0.01096 (13)
0.0193
−0.05840 (13)
−0.0970
−0.07174 (13)
−0.1192
−0.01541 (15)
−0.0244
0.39076 (11)
0.43743 (12)
0.4853
0.41512 (13)
0.4477
0.34587 (13)
0.3305
0.29893 (13)
0.2510
0.0213 (4)
0.0265 (5)
0.032*
0.0311 (5)
0.037*
0.0327 (5)
0.039*
0.0362 (6)
0.043*
0.2737 (2)
0.2304
0.05466 (14)
0.0931
0.32169 (12)
0.2890
0.0302 (5)
0.036*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
O1
O4
C2
C3
C4
C5
C6
C7
0.0270 (8)
0.0286 (8)
0.0262 (8)
0.0346 (9)
0.0250 (11)
0.0196 (10)
0.0221 (10)
0.0291 (12)
0.0318 (13)
0.0277 (12)
0.0240 (11)
0.0193 (10)
0.0232 (10)
0.0246 (11)
0.0351 (12)
0.0421 (14)
0.0438 (15)
0.075 (2)
0.0681 (19)
0.0497 (15)
0.0191 (10)
0.0285 (11)
0.0219 (11)
0.0193 (11)
0.0321 (13)
0.0238 (11)
0.0219 (8)
−0.0036 (6)
−0.0068 (7)
−0.0053 (8)
0.0000 (8)
0.0005 (6)
−0.0099 (7)
0.0021 (8)
0.0032 (8)
−0.0003 (8)
0.0006 (10)
0.0013 (11)
−0.0066 (10)
−0.0038 (9)
0.0029 (8)
0.0008 (8)
0.0037 (9)
0.0044 (9)
0.0092 (10)
0.0143 (12)
0.0111 (11)
0.0056 (10)
0.0049 (9)
0.0014 (8)
−0.0012 (8)
−0.0073 (9)
−0.0011 (10)
0.0016 (11)
0.0000 (9)
−0.0032 (6)
0.0148 (8)
−0.0006 (8)
−0.0022 (8)
0.0019 (9)
0.0432 (10)
0.0225 (10)
0.0278 (11)
0.0310 (12)
0.0409 (14)
0.0575 (17)
0.0512 (15)
0.0307 (12)
0.0279 (11)
0.0317 (12)
0.0296 (11)
0.0263 (11)
0.0351 (13)
0.0362 (14)
0.0351 (14)
0.0325 (14)
0.0279 (12)
0.0276 (11)
0.0286 (12)
0.0470 (14)
0.0528 (16)
0.0307 (13)
0.0291 (12)
0.0199 (10)
0.0184 (10)
0.0195 (10)
0.0240 (11)
0.0216 (11)
0.0211 (11)
0.0283 (11)
0.0198 (10)
0.0161 (10)
0.0202 (10)
0.0215 (11)
0.0268 (12)
0.0501 (16)
0.0267 (13)
0.0232 (12)
0.0228 (11)
0.0162 (9)
0.0009 (8)
−0.0027 (9)
−0.0062 (10)
−0.0014 (9)
0.0019 (9)
0.0023 (8)
0.0005 (8)
0.0078 (10)
0.0059 (11)
−0.0053 (10)
−0.0056 (9)
−0.0040 (8)
0.0000 (8)
−0.0057 (8)
−0.0101 (9)
−0.0098 (10)
−0.0061 (11)
−0.0146 (13)
−0.0099 (12)
−0.0109 (10)
0.0025 (8)
C8
C9
C10
C11
C12
C13
C14
C15
C16
C17
C18
C19
C20
C21
C22
C23
0.0000 (8)
−0.0077 (9)
−0.0108 (10)
−0.0207 (12)
−0.0264 (13)
−0.0093 (11)
−0.0037 (10)
−0.0041 (8)
−0.0037 (8)
−0.0029 (9)
−0.0017 (9)
0.0033 (11)
0.0059 (9)
0.0202 (10)
0.0194 (10)
0.0231 (11)
0.0438 (14)
0.0354 (12)
0.0054 (9)
0.0093 (10)
−0.0071 (10)
−0.0072 (10)
0.0036 (9)
Geometric parameters (Å, º)
O1—C9
O1—C2
O4—C4
C2—C3
C2—C18
C2—H2
1.365 (2)
C12—C17
1.3900
1.459 (2)
1.223 (3)
1.504 (3)
1.529 (3)
1.0000
C13—C14
C13—H13
C14—C15
C14—H14
C15—C16
1.3900
0.9500
1.3900
0.9500
1.3900
Acta Cryst. (2020). C76
sup-3

supporting information
C3—C11
C3—C4
C4—C10
C5—C6
C5—C10
C5—H5
C6—C7
C6—H6
C7—C8
C7—H7
C8—C9
C8—H8
C9—C10
C11—C12
C11—H11
C12—C13
1.349 (3)
1.485 (3)
1.472 (3)
1.378 (3)
1.406 (3)
0.9500
1.390 (4)
0.9500
1.381 (3)
0.9500
1.395 (3)
0.9500
1.392 (3)
1.468 (2)
0.9500
C15—H15
C16—C17
C16—H16
C17—H17
C18—C23
C18—C19
C19—C20
C19—H19
C20—C21
C20—H20
C21—C22
C21—H21
C22—C23
C22—H22
C23—H23
0.9500
1.3900
0.9500
0.9500
1.375 (3)
1.391 (3)
1.383 (3)
0.9500
1.377 (3)
0.9500
1.381 (3)
0.9500
1.395 (3)
0.9500
0.9500
1.3900
C9—O1—C2
O1—C2—C3
O1—C2—C18
C3—C2—C18
O1—C2—H2
C3—C2—H2
C18—C2—H2
C11—C3—C4
C11—C3—C2
C4—C3—C2
O4—C4—C10
O4—C4—C3
C10—C4—C3
C6—C5—C10
C6—C5—H5
C10—C5—H5
C5—C6—C7
C5—C6—H6
C7—C6—H6
C8—C7—C6
C8—C7—H7
C6—C7—H7
C7—C8—C9
C7—C8—H8
C9—C8—H8
O1—C9—C10
O1—C9—C8
C10—C9—C8
C9—C10—C5
C9—C10—C4
C5—C10—C4
117.18 (16)
112.51 (16)
108.33 (15)
114.39 (17)
107.1
C13—C12—C11
C17—C12—C11
C14—C13—C12
C14—C13—H13
C12—C13—H13
C13—C14—C15
C13—C14—H14
C15—C14—H14
C14—C15—C16
C14—C15—H15
C16—C15—H15
C17—C16—C15
C17—C16—H16
C15—C16—H16
C16—C17—C12
C16—C17—H17
C12—C17—H17
C23—C18—C19
C23—C18—C2
C19—C18—C2
C20—C19—C18
C20—C19—H19
C18—C19—H19
C21—C20—C19
C21—C20—H20
C19—C20—H20
C20—C21—C22
C20—C21—H21
C22—C21—H21
C21—C22—C23
C21—C22—H22
124.12 (12)
115.88 (12)
120.0
120.0
120.0
120.0
120.0
120.0
120.0
120.0
120.0
120.0
120.0
120.0
120.0
120.0
120.0
118.4 (2)
123.52 (18)
118.04 (19)
120.9 (2)
119.5
119.5
120.3 (2)
119.8
119.8
119.3 (2)
120.3
120.3
120.2 (2)
119.9
107.1
107.1
117.01 (19)
125.86 (19)
117.13 (17)
121.6 (2)
122.62 (19)
115.69 (18)
120.5 (2)
119.8
119.8
119.6 (2)
120.2
120.2
120.9 (2)
119.6
119.6
119.6 (2)
120.2
120.2
122.82 (18)
116.91 (19)
120.2 (2)
119.17 (19)
120.21 (19)
120.3 (2)
Acta Cryst. (2020). C76
sup-4

supporting information
C3—C11—C12
C3—C11—H11
C12—C11—H11
C13—C12—C17
131.7 (2)
114.2
114.2
C23—C22—H22
C18—C23—C22
C18—C23—H23
C22—C23—H23
119.9
120.8 (2)
119.6
120.0
119.6
C9—O1—C2—C3
C9—O1—C2—C18
O1—C2—C3—C11
C18—C2—C3—C11
O1—C2—C3—C4
C18—C2—C3—C4
C11—C3—C4—O4
C2—C3—C4—O4
C11—C3—C4—C10
C2—C3—C4—C10
C10—C5—C6—C7
C5—C6—C7—C8
C6—C7—C8—C9
C2—O1—C9—C10
C2—O1—C9—C8
C7—C8—C9—O1
C7—C8—C9—C10
O1—C9—C10—C5
C8—C9—C10—C5
O1—C9—C10—C4
C8—C9—C10—C4
C6—C5—C10—C9
C6—C5—C10—C4
O4—C4—C10—C9
C3—C4—C10—C9
O4—C4—C10—C5
−42.9 (2)
84.6 (2)
−141.2 (2)
94.6 (2)
C3—C4—C10—C5
C4—C3—C11—C12
C2—C3—C11—C12
177.17 (19)
−179.93 (19)
0.0 (4)
−26.0 (3)
153.9 (2)
0.0
179.93 (16)
0.0
0.0
C3—C11—C12—C13
C3—C11—C12—C17
C17—C12—C13—C14
C11—C12—C13—C14
C12—C13—C14—C15
C13—C14—C15—C16
C14—C15—C16—C17
C15—C16—C17—C12
C13—C12—C17—C16
C11—C12—C17—C16
O1—C2—C18—C23
C3—C2—C18—C23
O1—C2—C18—C19
C3—C2—C18—C19
C23—C18—C19—C20
C2—C18—C19—C20
C18—C19—C20—C21
C19—C20—C21—C22
C20—C21—C22—C23
C19—C18—C23—C22
C2—C18—C23—C22
C21—C22—C23—C18
38.7 (2)
−85.5 (2)
−10.5 (3)
169.6 (2)
166.58 (19)
−13.4 (3)
−1.7 (4)
2.4 (4)
−0.3 (3)
21.3 (3)
−162.10 (17)
−179.08 (19)
−2.4 (3)
179.55 (18)
3.1 (3)
6.5 (3)
−170.01 (19)
−1.0 (3)
0.0
0.0
0.0
−179.93 (15)
−123.2 (2)
3.2 (3)
57.6 (2)
−176.08 (17)
1.1 (3)
−179.64 (17)
−0.5 (3)
−0.4 (3)
0.7 (3)
−0.7 (3)
−180.0 (2)
−0.2 (4)
172.0 (2)
167.2 (2)
−9.8 (3)
−5.8 (3)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
C11—H11···O4i
C17—H17···O4i
C21—H21···O4ii
0.95
0.95
0.95
2.47
2.64
2.68
3.353 (3)
3.353 (2)
3.267 (3)
154
132
120
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2.
(E)-3-(4-Methylbenzylidene)-2-phenylchroman-4-one (compound_II_AAG9)
Crystal data
C23H18O2
Mr = 326.37
Monoclinic, P21/c
a = 16.6799 (5) Å
b = 7.9102 (2) Å
c = 13.1511 (3) Å
β = 98.558 (3)°
V = 1715.85 (8) Å3
Z = 4
F(000) = 688
Dx = 1.263 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Acta Cryst. (2020). C76
sup-5

supporting information
Cell parameters from 4576 reflections
θ = 3.2–35.6°
µ = 0.08 mm−1
T = 100 K
Needle, colorless
0.28 × 0.1 × 0.1 mm
Data collection
Rigaku OD SuperNova Dual source
diffractometer with an Atlas detector
Radiation source: micro-focus sealed X-ray
tube, SuperNova (Mo) X-ray Source
Mirror monochromator
Tmin = 0.833, Tmax = 1.000
13962 measured reflections
3550 independent reflections
2927 reflections with I > 2σ(I)
R
int = 0.031
Detector resolution: 10.4498 pixels mm-1
ω scans
θmax = 26.5°, θmin = 3.1°
h = −20→20
k = −9→9
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
l = −11→16
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.040
wR(F2) = 0.107
S = 1.05
3550 reflections
227 parameters
0 restraints
Primary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
2
w = 1/[σ2(Fo ) + (0.0551P)2 + 0.3869P]
2
where P = (Fo + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.19 e Å−3
Δρmin = −0.23 e Å−3
Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance
matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles;
correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate
(isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
O1
O4
C2
H2
C3
C4
C5
H5
C6
H6
C7
H7
C8
H8
C9
C10
0.13016 (5)
0.24076 (6)
0.21464 (7)
0.2425
0.25695 (7)
0.20880 (8)
0.07131 (8)
0.0945
−0.01103 (8)
−0.0445
−0.04520 (8)
−0.1021
0.69823 (11)
0.72695 (14)
0.64404 (15)
0.6974
0.70595 (14)
0.70299 (15)
0.65060 (17)
0.6518
0.62868 (19)
0.6141
0.6279 (2)
0.6131
0.61728 (6)
0.91481 (7)
0.63602 (9)
0.5818
0.73857 (9)
0.82561 (9)
0.87504 (10)
0.9455
0.84830 (11)
0.9001
0.74468 (11)
0.7265
0.0197 (2)
0.0330 (3)
0.0167 (2)
0.020*
0.0169 (2)
0.0199 (3)
0.0249 (3)
0.030*
0.0304 (3)
0.036*
0.0325 (3)
0.039*
0.00253 (8)
−0.0212
0.08575 (8)
0.12126 (7)
0.64841 (18)
0.6477
0.67000 (15)
0.67117 (15)
0.66811 (10)
0.5978
0.69525 (9)
0.79869 (9)
0.0273 (3)
0.033*
0.0195 (3)
0.0196 (3)
Acta Cryst. (2020). C76
sup-6

supporting information
C11
H11
C12
C13
H13
C14
H14
C15
C16
H16
C17
H17
C18
H18A
H18B
H18C
C21
C22
H22
C23
H23
C24
H24
C25
H25
C26
H26
0.33397 (7)
0.3504
0.39695 (7)
0.39774 (7)
0.3545
0.46100 (8)
0.4597
0.52641 (8)
0.52603 (8)
0.5699
0.46310 (8)
0.4646
0.59644 (9)
0.6390
0.6182
0.5776
0.21801 (7)
0.18813 (7)
0.1658
0.19088 (8)
0.1705
0.22339 (8)
0.2254
0.25287 (8)
0.2749
0.76156 (15)
0.7991
0.77435 (15)
0.68092 (16)
0.6054
0.69780 (17)
0.6347
0.80485 (17)
0.89659 (18)
0.9705
0.88198 (17)
0.9462
0.8178 (2)
0.7379
0.9331
0.7908
0.45373 (15)
0.38872 (16)
0.4631
0.21637 (17)
0.1731
0.10705 (17)
−0.0109
0.17031 (17)
0.0955
0.75777 (9)
0.8263
0.69160 (9)
0.60070 (9)
0.5780
0.54379 (9)
0.4821
0.57477 (10)
0.66538 (11)
0.6884
0.72228 (10)
0.7836
0.51466 (12)
0.5426
0.5200
0.4423
0.62104 (9)
0.52380 (9)
0.4702
0.50521 (10)
0.4390
0.58321 (11)
0.5704
0.67978 (11)
0.7332
0.0185 (3)
0.022*
0.0192 (3)
0.0210 (3)
0.025*
0.0225 (3)
0.027*
0.0254 (3)
0.0295 (3)
0.035*
0.0253 (3)
0.030*
0.0346 (3)
0.052*
0.052*
0.052*
0.0177 (3)
0.0220 (3)
0.026*
0.0267 (3)
0.032*
0.0284 (3)
0.034*
0.0285 (3)
0.034*
0.25024 (8)
0.2706
0.34321 (16)
0.3860
0.69859 (10)
0.7649
0.0227 (3)
0.027*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
O1
O4
C2
C3
C4
C5
C6
C7
0.0176 (4)
0.0259 (5)
0.0152 (6)
0.0197 (6)
0.0219 (6)
0.0258 (7)
0.0251 (7)
0.0180 (7)
0.0211 (7)
0.0202 (6)
0.0207 (6)
0.0220 (6)
0.0174 (6)
0.0184 (6)
0.0214 (6)
0.0210 (6)
0.0214 (7)
0.0237 (5)
0.0560 (7)
0.0182 (6)
0.0134 (6)
0.0207 (6)
0.0278 (7)
0.0378 (8)
0.0430 (9)
0.0343 (8)
0.0177 (6)
0.0180 (6)
0.0168 (6)
0.0197 (6)
0.0213 (6)
0.0264 (7)
0.0269 (7)
0.0298 (7)
0.0177 (4)
0.0045 (3)
−0.0066 (5)
0.0011 (4)
0.0020 (4)
0.0009 (5)
0.0013 (5)
−0.0009 (6)
0.0000 (6)
0.0034 (6)
0.0029 (5)
0.0016 (5)
0.0010 (5)
0.0023 (5)
0.0005 (5)
0.0046 (5)
0.0024 (5)
−0.0074 (5)
0.0022 (3)
0.0030 (4)
0.0023 (4)
0.0022 (5)
0.0029 (5)
0.0062 (5)
0.0126 (6)
0.0055 (6)
0.0004 (5)
0.0047 (5)
0.0039 (5)
0.0011 (5)
0.0011 (5)
0.0004 (5)
0.0015 (5)
0.0062 (5)
0.0051 (6)
0.0018 (3)
−0.0072 (4)
0.0012 (4)
0.0006 (4)
−0.0007 (5)
−0.0014 (5)
−0.0028 (6)
−0.0056 (6)
−0.0019 (6)
−0.0003 (5)
−0.0017 (5)
−0.0011 (4)
0.0018 (5)
−0.0010 (5)
−0.0006 (5)
0.0031 (5)
−0.0058 (6)
0.0170 (4)
0.0167 (5)
0.0174 (6)
0.0173 (6)
0.0219 (6)
0.0308 (7)
0.0371 (8)
0.0254 (6)
0.0211 (6)
0.0203 (6)
0.0162 (5)
0.0199 (6)
0.0224 (6)
0.0194 (6)
0.0291 (7)
0.0376 (8)
C8
C9
C10
C11
C12
C13
C14
C15
C16
Acta Cryst. (2020). C76
sup-7

supporting information
C17
C18
C21
C22
C23
C24
C25
C26
0.0235 (7)
0.0244 (7)
0.0146 (6)
0.0201 (6)
0.0233 (7)
0.0249 (7)
0.0272 (7)
0.0222 (6)
0.0270 (7)
0.0407 (9)
0.0182 (6)
0.0230 (7)
0.0261 (7)
0.0166 (6)
0.0211 (7)
0.0215 (6)
0.0251 (6)
0.0413 (8)
0.0212 (6)
0.0229 (6)
0.0320 (7)
0.0459 (8)
0.0376 (8)
0.0243 (6)
−0.0031 (5)
−0.0007 (6)
−0.0013 (4)
−0.0012 (5)
−0.0058 (5)
−0.0014 (5)
0.0036 (5)
0.0024 (5)
0.0132 (6)
0.0055 (5)
0.0030 (5)
0.0080 (5)
0.0132 (6)
0.0066 (6)
0.0038 (5)
−0.0068 (5)
0.0009 (7)
−0.0009 (5)
−0.0015 (5)
−0.0094 (5)
−0.0038 (6)
0.0062 (6)
0.0020 (5)
0.0012 (5)
Geometric parameters (Å, º)
O1—C9
O1—C2
O4—C4
C2—C3
C2—C21
C2—H2
C3—C11
C3—C4
C4—C10
C5—C6
C5—C10
C5—H5
C6—C7
C6—H6
C7—C8
C7—H7
C8—C9
C8—H8
C9—C10
C11—C12
C11—H11
C12—C17
C12—C13
1.3696 (14)
C13—C14
1.3879 (17)
0.9500
1.4582 (14)
1.2288 (15)
1.5078 (16)
1.5204 (16)
1.0000
1.3458 (17)
1.4932 (16)
1.4720 (17)
1.3770 (19)
1.4064 (17)
0.9500
1.397 (2)
0.9500
1.3830 (19)
0.9500
1.3915 (18)
0.9500
C13—H13
C14—C15
C14—H14
C15—C16
C15—C18
C16—C17
C16—H16
C17—H17
C18—H18A
C18—H18B
C18—H18C
C21—C26
C21—C22
C22—C23
C22—H22
C23—C24
C23—H23
C24—C25
C24—H24
C25—C26
C25—H25
C26—H26
1.3933 (19)
0.9500
1.3960 (19)
1.5082 (18)
1.3817 (19)
0.9500
0.9500
0.9800
0.9800
0.9800
1.3893 (17)
1.3995 (17)
1.3870 (18)
0.9500
1.389 (2)
0.9500
1.385 (2)
0.9500
1.3917 (19)
0.9500
1.4006 (17)
1.4637 (17)
0.9500
1.4046 (17)
1.4072 (17)
0.9500
C9—O1—C2
O1—C2—C3
O1—C2—C21
C3—C2—C21
O1—C2—H2
C3—C2—H2
C21—C2—H2
C11—C3—C4
C11—C3—C2
C4—C3—C2
O4—C4—C10
O4—C4—C3
C10—C4—C3
116.24 (9)
111.57 (9)
108.82 (9)
114.59 (10)
107.2
C14—C13—H13
C12—C13—H13
C13—C14—C15
C13—C14—H14
C15—C14—H14
C14—C15—C16
C14—C15—C18
C16—C15—C18
C17—C16—C15
C17—C16—H16
C15—C16—H16
C16—C17—C12
C16—C17—H17
119.6
119.6
121.73 (12)
119.1
119.1
117.56 (12)
121.46 (12)
120.96 (13)
121.27 (12)
119.4
119.4
121.52 (12)
119.2
107.2
107.2
117.95 (10)
125.50 (11)
116.55 (10)
122.00 (11)
121.53 (11)
116.47 (10)
Acta Cryst. (2020). C76
sup-8

supporting information
C6—C5—C10
C6—C5—H5
C10—C5—H5
C5—C6—C7
C5—C6—H6
C7—C6—H6
C8—C7—C6
C8—C7—H7
C6—C7—H7
C7—C8—C9
C7—C8—H8
C9—C8—H8
O1—C9—C8
O1—C9—C10
C8—C9—C10
C9—C10—C5
C9—C10—C4
C5—C10—C4
C3—C11—C12
C3—C11—H11
C12—C11—H11
C17—C12—C13
C17—C12—C11
C13—C12—C11
C14—C13—C12
120.44 (12)
119.8
119.8
119.76 (12)
120.1
120.1
120.96 (13)
119.5
119.5
119.21 (12)
120.4
120.4
117.26 (11)
121.89 (11)
120.77 (11)
118.87 (12)
119.72 (11)
121.33 (11)
131.34 (11)
114.3
C12—C17—H17
C15—C18—H18A
C15—C18—H18B
H18A—C18—H18B
C15—C18—H18C
H18A—C18—H18C
H18B—C18—H18C
C26—C21—C22
C26—C21—C2
119.2
109.5
109.5
109.5
109.5
109.5
109.5
119.07 (12)
123.07 (11)
117.85 (11)
120.37 (12)
119.8
119.8
120.09 (12)
120.0
120.0
119.90 (12)
120.0
120.0
120.11 (13)
119.9
C22—C21—C2
C23—C22—C21
C23—C22—H22
C21—C22—H22
C22—C23—C24
C22—C23—H23
C24—C23—H23
C25—C24—C23
C25—C24—H24
C23—C24—H24
C24—C25—C26
C24—C25—H25
C26—C25—H25
C21—C26—C25
C21—C26—H26
C25—C26—H26
114.3
117.13 (11)
118.27 (11)
124.55 (11)
120.78 (12)
119.9
120.45 (12)
119.8
119.8
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
C2—H2···O4i
C5—H5···O1ii
C24—H24···O4iii
1.00
0.95
0.95
2.27
2.54
2.71
3.1737 (14)
3.4076 (15)
3.4871 (17)
149
152
140
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+1/2, z−1/2.
(E)-3-(3-Methylbenzylidene)-2-phenylchroman-4-one (compound_III_AAG1)
Crystal data
C23H18O2
Z = 2
Mr = 326.37
Triclinic, P1
F(000) = 344
Dx = 1.275 Mg m−3
a = 8.9094 (3) Å
b = 9.6578 (3) Å
c = 10.9044 (4) Å
α = 104.378 (3)°
β = 109.425 (3)°
γ = 91.902 (3)°
V = 850.24 (5) Å3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 3948 reflections
θ = 3.5–36.1°
µ = 0.08 mm−1
T = 100 K
Needle, colorless
0.28 × 0.1 × 0.08 mm
Acta Cryst. (2020). C76
sup-9

supporting information
Data collection
Rigaku OD SuperNova Dual source
diffractometer with an Atlas detector
Radiation source: micro-focus sealed X-ray
tube, SuperNova (Mo) X-ray Source
Detector resolution: 10.4498 pixels mm-1
ω scans
7284 measured reflections
3509 independent reflections
2999 reflections with I > 2σ(I)
R
int = 0.021
θ
max = 26.5°, θmin = 3.1°
h = −11→11
k = −12→12
l = −13→10
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
T
min = 0.736, Tmax = 1.000
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.037
wR(F2) = 0.098
S = 1.04
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
2
w = 1/[σ2(Fo ) + (0.0439P)2 + 0.2079P]
2
where P = (Fo + 2Fc2)/3
3509 reflections
227 parameters
0 restraints
(Δ/σ)max = 0.001
Δρmax = 0.24 e Å−3
Δρmin = −0.21 e Å−3
Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance
matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles;
correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate
(isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
O1
O4
C21
C12
C2
0.57118 (10)
0.38766 (10)
0.66313 (13)
0.89045 (14)
0.66990 (14)
0.7834
0.44640 (9)
0.03505 (9)
0.29543 (13)
0.16807 (12)
0.33222 (12)
0.3701
0.37188 (8)
0.32719 (8)
0.20350 (11)
0.54388 (12)
0.35024 (11)
0.4101
0.0200 (2)
0.0229 (2)
0.0170 (2)
0.0192 (3)
0.0172 (2)
0.021*
H2
C3
0.61964 (14)
0.71562 (14)
0.6638
0.40917 (14)
0.44417 (14)
0.66779 (14)
0.6718
0.34138 (14)
0.99590 (15)
0.9549
0.95460 (15)
0.8844
0.20436 (12)
0.13781 (13)
0.0611
0.40489 (13)
0.15501 (13)
0.15547 (13)
0.0796
0.26263 (13)
0.20421 (13)
0.2119
0.15826 (13)
0.1306
0.39022 (11)
0.47467 (11)
0.4920
0.31451 (11)
0.33244 (11)
0.13257 (12)
0.1744
0.28726 (11)
0.48267 (12)
0.3926
0.67717 (12)
0.7185
0.0176 (2)
0.0188 (3)
0.023*
0.0188 (3)
0.0179 (2)
0.0204 (3)
0.024*
0.0188 (3)
0.0221 (3)
0.026*
0.0203 (3)
0.024*
C11
H11
C9
C4
C26
H26
C10
C13
H13
C17
H17
C16
C5
1.11883 (15)
0.17385 (15)
0.1266
0.18806 (13)
0.22886 (14)
0.1325
0.75045 (12)
0.22882 (12)
0.2086
0.0215 (3)
0.0228 (3)
0.027*
H5
Acta Cryst. (2020). C76
sup-10

supporting information
C22
H22
C25
H25
C24
H24
C14
H14
C15
H15
C23
H23
C8
0.65751 (14)
0.6544
0.66659 (15)
0.6695
0.66114 (14)
0.6607
1.16003 (15)
1.2311
1.22082 (15)
1.3335
0.65634 (15)
0.6522
0.31165 (16)
0.3579
0.40519 (13)
0.5013
0.12572 (14)
0.0297
0.23528 (14)
0.2149
0.22879 (14)
0.2514
0.22054 (13)
0.2373
0.37523 (14)
0.4508
0.51168 (14)
0.6084
0.14018 (12)
0.1876
0.00015 (12)
−0.0476
−0.06185 (12)
−0.1518
0.55301 (13)
0.5103
0.68555 (12)
0.7327
0.00852 (12)
−0.0336
0.28802 (12)
0.3085
0.0208 (3)
0.025*
0.0230 (3)
0.028*
0.0221 (3)
0.027*
0.0249 (3)
0.030*
0.0234 (3)
0.028*
0.0232 (3)
0.028*
0.0243 (3)
0.029*
H8
C6
H6
0.07720 (15)
−0.0359
0.33358 (16)
0.3095
0.20038 (13)
0.1599
0.0274 (3)
0.033*
C7
H7
0.14682 (16)
0.0801
0.47552 (15)
0.5482
0.23157 (13)
0.2138
0.0279 (3)
0.033*
C18
H18A
H18B
H18C
1.18325 (16)
1.1300
1.1624
0.18957 (15)
0.1062
0.2785
0.89766 (12)
0.9099
0.9527
0.0283 (3)
0.042*
0.042*
1.2991
0.1850
0.9259
0.042*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
O1
O4
C21
C12
C2
C3
C11
C9
0.0226 (4)
0.0240 (4)
0.0138 (5)
0.0228 (6)
0.0176 (5)
0.0212 (6)
0.0230 (6)
0.0222 (6)
0.0225 (6)
0.0240 (6)
0.0214 (6)
0.0244 (6)
0.0252 (6)
0.0286 (7)
0.0224 (6)
0.0219 (6)
0.0268 (6)
0.0212 (6)
0.0251 (6)
0.0204 (6)
0.0243 (6)
0.0328 (7)
0.0158 (4)
0.0210 (5)
0.0185 (6)
0.0134 (6)
0.0157 (6)
0.0166 (6)
0.0162 (6)
0.0217 (6)
0.0191 (6)
0.0176 (6)
0.0221 (6)
0.0227 (7)
0.0155 (6)
0.0141 (6)
0.0290 (7)
0.0169 (6)
0.0195 (6)
0.0289 (7)
0.0256 (7)
0.0200 (6)
0.0247 (7)
0.0217 (7)
0.0191 (4)
0.0016 (3)
−0.0023 (3)
0.0001 (4)
0.0031 (4)
0.0013 (4)
0.0012 (4)
0.0001 (5)
0.0032 (5)
0.0004 (5)
0.0009 (5)
0.0032 (5)
0.0027 (5)
0.0038 (5)
0.0043 (5)
0.0013 (5)
0.0032 (5)
0.0015 (5)
0.0035 (5)
0.0016 (5)
0.0017 (5)
0.0052 (5)
0.0075 (5)
0.0072 (3)
0.0066 (4)
0.0045 (4)
0.0056 (5)
0.0051 (4)
0.0071 (4)
0.0083 (5)
0.0072 (4)
0.0078 (4)
0.0068 (5)
0.0079 (4)
0.0068 (5)
0.0088 (5)
0.0050 (5)
0.0086 (5)
0.0091 (5)
0.0076 (5)
0.0062 (5)
0.0105 (5)
0.0037 (5)
0.0099 (5)
0.0111 (5)
0.0009 (3)
0.0069 (4)
0.0046 (5)
0.0028 (4)
0.0031 (4)
0.0014 (4)
0.0022 (4)
0.0025 (5)
0.0027 (4)
0.0056 (5)
0.0043 (5)
0.0048 (5)
0.0055 (5)
0.0026 (5)
0.0067 (5)
0.0057 (5)
0.0019 (5)
0.0075 (5)
0.0044 (5)
0.0019 (5)
0.0127 (5)
0.0043 (5)
0.0226 (4)
0.0176 (5)
0.0191 (6)
0.0168 (5)
0.0141 (5)
0.0167 (5)
0.0121 (5)
0.0123 (5)
0.0191 (6)
0.0138 (5)
0.0180 (6)
0.0211 (6)
0.0181 (6)
0.0182 (6)
0.0245 (6)
0.0200 (6)
0.0167 (5)
0.0241 (6)
0.0242 (6)
0.0250 (6)
0.0194 (6)
C4
C26
C10
C13
C17
C16
C5
C22
C25
C24
C14
C15
C23
C8
Acta Cryst. (2020). C76
sup-11

supporting information
C6
C7
C18
0.0206 (6)
0.0301 (7)
0.0315 (7)
0.0400 (8)
0.0331 (8)
0.0295 (7)
0.0231 (6)
0.0238 (6)
0.0205 (6)
0.0072 (5)
0.0156 (6)
0.0051 (5)
0.0085 (5)
0.0115 (5)
0.0045 (5)
0.0098 (6)
0.0096 (6)
0.0073 (5)
Geometric parameters (Å, º)
O1—C9
1.3682 (14)
C17—H17
0.9500
O1—C2
O4—C4
1.4555 (14)
1.2281 (14)
1.3903 (17)
1.3953 (17)
1.5305 (15)
1.4004 (17)
1.4027 (16)
1.4695 (16)
1.5086 (16)
1.0000
1.3413 (17)
1.4881 (15)
0.9500
1.3938 (17)
1.4012 (17)
1.4762 (17)
1.3969 (16)
0.9500
C16—C15
C16—C18
C5—C6
1.3942 (18)
1.5105 (16)
1.3771 (19)
0.9500
1.3887 (17)
0.9500
1.3841 (18)
0.9500
1.3885 (18)
0.9500
1.3885 (18)
0.9500
0.9500
0.9500
1.3839 (18)
0.9500
C21—C26
C21—C22
C21—C2
C12—C13
C12—C17
C12—C11
C2—C3
C2—H2
C3—C11
C3—C4
C5—H5
C22—C23
C22—H22
C25—C24
C25—H25
C24—C23
C24—H24
C14—C15
C14—H14
C15—H15
C23—H23
C8—C7
C8—H8
C6—C7
C6—H6
C7—H7
C18—H18A
C18—H18B
C18—H18C
C11—H11
C9—C8
C9—C10
C4—C10
C26—C25
C26—H26
C10—C5
C13—C14
C13—H13
C17—C16
1.397 (2)
0.9500
0.9500
0.9800
0.9800
1.4043 (16)
1.3868 (17)
0.9500
1.3937 (17)
0.9800
C9—O1—C2
115.14 (9)
118.86 (11)
121.58 (10)
119.53 (11)
118.55 (11)
123.22 (10)
118.22 (11)
110.50 (9)
109.10 (9)
113.52 (9)
107.8
C17—C16—C18
C15—C16—C18
C6—C5—C10
C6—C5—H5
C10—C5—H5
120.52 (11)
121.13 (11)
120.87 (12)
119.6
119.6
120.62 (12)
119.7
119.7
120.39 (12)
119.8
119.8
119.46 (11)
120.3
C26—C21—C22
C26—C21—C2
C22—C21—C2
C13—C12—C17
C13—C12—C11
C17—C12—C11
O1—C2—C3
O1—C2—C21
C3—C2—C21
O1—C2—H2
C23—C22—C21
C23—C22—H22
C21—C22—H22
C24—C25—C26
C24—C25—H25
C26—C25—H25
C25—C24—C23
C25—C24—H24
C23—C24—H24
C13—C14—C15
C13—C14—H14
C15—C14—H14
C14—C15—C16
C3—C2—H2
107.8
107.8
C21—C2—H2
C11—C3—C4
C11—C3—C2
C4—C3—C2
C3—C11—C12
C3—C11—H11
118.88 (10)
126.48 (11)
114.58 (10)
128.46 (11)
115.8
120.3
120.26 (12)
119.9
119.9
120.92 (11)
Acta Cryst. (2020). C76
sup-12

supporting information
C12—C11—H11
O1—C9—C8
O1—C9—C10
C8—C9—C10
O4—C4—C10
O4—C4—C3
C10—C4—C3
C21—C26—C25
C21—C26—H26
C25—C26—H26
C9—C10—C5
C9—C10—C4
C5—C10—C4
C14—C13—C12
C14—C13—H13
C12—C13—H13
C16—C17—C12
C16—C17—H17
C12—C17—H17
C17—C16—C15
115.8
C14—C15—H15
C16—C15—H15
C24—C23—C22
C24—C23—H23
C22—C23—H23
C7—C8—C9
C7—C8—H8
C9—C8—H8
C5—C6—C7
C5—C6—H6
C7—C6—H6
C8—C7—C6
C8—C7—H7
C6—C7—H7
C16—C18—H18A
C16—C18—H18B
H18A—C18—H18B
C16—C18—H18C
H18A—C18—H18C
H18B—C18—H18C
119.5
119.5
120.31 (11)
119.8
119.8
119.42 (12)
120.3
120.3
119.48 (12)
120.3
120.3
120.90 (12)
119.5
119.5
109.5
109.5
109.5
109.5
109.5
109.5
117.18 (11)
122.27 (11)
120.51 (11)
121.96 (11)
122.58 (11)
115.40 (10)
120.37 (11)
119.8
119.8
118.78 (11)
119.87 (11)
121.05 (11)
120.24 (11)
119.9
119.9
121.63 (11)
119.2
119.2
118.32 (11)
C9—O1—C2—C3
C9—O1—C2—C21
C26—C21—C2—O1
C22—C21—C2—O1
C26—C21—C2—C3
C22—C21—C2—C3
O1—C2—C3—C11
C21—C2—C3—C11
O1—C2—C3—C4
C21—C2—C3—C4
C4—C3—C11—C12
C2—C3—C11—C12
C13—C12—C11—C3
C17—C12—C11—C3
C2—O1—C9—C8
C2—O1—C9—C10
C11—C3—C4—O4
C2—C3—C4—O4
C11—C3—C4—C10
C2—C3—C4—C10
C22—C21—C26—C25
C2—C21—C26—C25
O1—C9—C10—C5
C8—C9—C10—C5
O1—C9—C10—C4
C8—C9—C10—C4
O4—C4—C10—C9
−51.97 (12)
73.51 (11)
C3—C4—C10—C9
O4—C4—C10—C5
C3—C4—C10—C5
C17—C12—C13—C14
C11—C12—C13—C14
C13—C12—C17—C16
C11—C12—C17—C16
C12—C17—C16—C15
C12—C17—C16—C18
C9—C10—C5—C6
−7.36 (15)
−3.72 (17)
178.94 (10)
0.34 (18)
−178.77 (12)
2.12 (18)
−178.73 (11)
−3.55 (18)
174.54 (12)
−0.92 (17)
172.84 (11)
0.09 (17)
177.99 (11)
0.16 (18)
−0.21 (18)
−1.3 (2)
−0.2 (2)
2.57 (19)
−175.51 (12)
0.20 (18)
−0.15 (18)
−179.21 (10)
−1.43 (17)
−0.74 (18)
−0.26 (18)
1.35 (19)
−145.49 (10)
36.67 (14)
−21.79 (15)
160.38 (10)
−127.71 (12)
109.35 (13)
49.49 (12)
−73.45 (13)
−179.62 (11)
−2.5 (2)
−39.46 (19)
141.43 (13)
−157.01 (10)
25.25 (14)
−20.52 (17)
162.05 (11)
156.80 (11)
−20.63 (14)
−0.10 (17)
−177.95 (11)
179.68 (10)
2.01 (17)
C4—C10—C5—C6
C26—C21—C22—C23
C2—C21—C22—C23
C21—C26—C25—C24
C26—C25—C24—C23
C12—C13—C14—C15
C13—C14—C15—C16
C17—C16—C15—C14
C18—C16—C15—C14
C25—C24—C23—C22
C21—C22—C23—C24
O1—C9—C8—C7
C10—C9—C8—C7
C10—C5—C6—C7
C9—C8—C7—C6
C5—C6—C7—C8
5.84 (16)
−171.83 (10)
169.98 (10)
Acta Cryst. (2020). C76
sup-13

supporting information
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
C11—H11···O4i
C17—H17···O4i
C24—H24···O4ii
0.95
0.95
0.95
2.54
2.69
2.60
3.3635 (14)
3.5025 (15)
3.2731 (15)
145
144
128
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z.
(E)-3-(4-Methoxybenzylidene)-2-phenylchroman-4-one (compound_IV_AAG2)
Crystal data
C23H18O3
Mr = 342.37
F(000) = 2160
Dx = 1.306 Mg m−3
Monoclinic, P21/n
a = 23.4111 (3) Å
b = 8.0027 (1) Å
c = 28.1094 (5) Å
β = 97.156 (1)°
V = 5225.33 (13) Å3
Z = 12
Cu Kα radiation, λ = 1.54184 Å
Cell parameters from 7810 reflections
θ = 2.6–74.1°
µ = 0.69 mm−1
T = 100 K
Needle, colorless
0.28 × 0.1 × 0.08 mm
Data collection
Rigaku OD SuperNova Dual source
diffractometer with an Atlas detector
ω scans
9323 independent reflections
7742 reflections with I > 2σ(I)
R
int = 0.022
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
θmax = 67.5°, θmin = 2.3°
h = −26→28
k = −9→7
T
min = 0.997, Tmax = 1.000
15971 measured reflections
l = −33→30
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.038
wR(F2) = 0.104
S = 1.01
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
2
w = 1/[σ2(Fo ) + (0.0515P)2 + 0.9818P]
2
where P = (Fo + 2Fc2)/3
9323 reflections
706 parameters
0 restraints
(Δ/σ)max = 0.001
Δρmax = 0.20 e Å−3
Δρmin = −0.21 e Å−3
Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance
matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles;
correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate
(isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
O1
O4
O3
0.10459 (3)
0.26145 (4)
0.31526 (4)
0.83638 (11)
0.77397 (13)
0.78657 (13)
0.53474 (3)
0.48650 (3)
0.78489 (3)
0.01769 (18)
0.0270 (2)
0.0293 (2)
Acta Cryst. (2020). C76
sup-14

supporting information
C5
C4
C6
H6
0.16094 (5)
0.21516 (5)
0.16063 (6)
0.1960
0.81050 (15)
0.80412 (15)
0.79075 (18)
0.7805
0.46836 (4)
0.50102 (4)
0.41871 (5)
0.4057
0.0195 (3)
0.0190 (3)
0.0248 (3)
0.030*
C3
0.21023 (5)
0.25594 (5)
0.2877
0.29676 (6)
0.05653 (6)
0.0210
0.83055 (14)
0.78916 (15)
0.7476
0.79508 (16)
0.82182 (18)
0.8326
0.55297 (4)
0.58462 (5)
0.5702
0.73726 (5)
0.45664 (5)
0.4694
0.0171 (2)
0.0186 (2)
0.022*
0.0221 (3)
0.0253 (3)
0.030*
C17
H17
C21
C9
H9
C19
H19
C23
H23
C18
C16
H16
C2
0.23508 (5)
0.2033
0.31335 (5)
0.3355
0.26619 (5)
0.10377 (5)
0.0767
0.15441 (5)
0.1505
0.88924 (15)
0.9545
0.70289 (17)
0.6391
0.79578 (15)
1.16182 (16)
1.0927
0.89981 (15)
0.8617
0.66704 (4)
0.6534
0.65885 (5)
0.6393
0.63689 (5)
0.58418 (5)
0.5973
0.56591 (4)
0.5992
0.0187 (2)
0.022*
0.0229 (3)
0.028*
0.0192 (3)
0.0214 (3)
0.026*
0.0162 (2)
0.019*
H2
C14
H14
C15
H15
C10
C11
C12
H12
C20
H20
C13
H13
C8
0.13611 (6)
0.1310
0.09655 (6)
0.0646
0.10837 (5)
0.15050 (5)
0.19031 (5)
0.2224
0.24966 (5)
0.2276
1.43522 (16)
1.5530
1.33437 (17)
1.3830
0.82584 (15)
1.08964 (15)
1.19147 (16)
1.1431
0.88868 (16)
0.9519
0.56434 (5)
0.5636
0.58351 (5)
0.5961
0.48687 (4)
0.56562 (4)
0.54688 (4)
0.5345
0.71658 (5)
0.7363
0.0252 (3)
0.030*
0.0251 (3)
0.030*
0.0184 (2)
0.0173 (2)
0.0194 (3)
0.023*
0.0202 (3)
0.024*
0.18315 (6)
0.2104
0.05741 (6)
0.0222
1.36457 (17)
1.4341
0.8019 (2)
0.7989
0.54629 (5)
0.5336
0.40788 (5)
0.3871
0.0236 (3)
0.028*
0.0317 (3)
0.038*
H8
C22
H22
C7
0.32840 (6)
0.3603
0.10937 (6)
0.1094
0.70158 (17)
0.6370
0.7862 (2)
0.7724
0.70782 (5)
0.7215
0.38870 (5)
0.3551
0.0251 (3)
0.030*
0.0307 (3)
0.037*
H7
C211
H21A
H21B
H21C
O31
O34
C40
O33
C41
C42
H42
0.28785 (6)
0.2464
0.2946
0.8935 (2)
0.8712
1.0105
0.81596 (5)
0.8119
0.8080
0.0321 (3)
0.048*
0.048*
0.3038
0.8721
0.8493
0.048*
0.56062 (3)
0.40526 (4)
0.55790 (5)
0.34425 (4)
0.51536 (5)
0.47572 (6)
0.4431
0.27594 (11)
0.20680 (13)
0.26249 (15)
0.32326 (14)
0.53223 (15)
0.63647 (16)
0.5901
0.79683 (3)
0.84703 (3)
0.84483 (4)
0.55019 (3)
0.76805 (4)
0.78610 (4)
0.7983
0.01768 (18)
0.0264 (2)
0.0185 (2)
0.0311 (2)
0.0174 (2)
0.0209 (3)
0.025*
Acta Cryst. (2020). C76
sup-15

supporting information
C33
C46
H46
C48
C36
H36
C47
H47
C52
H52
C35
C43
H43
C34
C45
H45
C37
H37
C51
C50
H50
C44
H44
C49
H49
C39
H39
C32
H32
C53
H53
C38
H38
C511
H51A
H51B
H51C
O61
O64
O63
C63
C70
C62
H62
C76
H76
C77
H77
0.45460 (5)
0.56266 (6)
0.5895
0.39692 (5)
0.50724 (6)
0.4722
0.40779 (5)
0.3763
0.33472 (6)
0.3035
0.50597 (5)
0.48379 (6)
0.4567
0.45110 (5)
0.57070 (6)
0.6031
0.55895 (6)
0.5596
0.36454 (6)
0.41129 (5)
0.4324
0.53120 (7)
0.5368
0.42686 (5)
0.4586
0.61035 (6)
0.6456
0.51044 (5)
0.5133
0.35057 (6)
0.3295
0.61048 (6)
0.6461
0.36840 (6)
0.4095
0.3636
0.27542 (15)
0.60212 (17)
0.5315
0.26975 (16)
0.22330 (17)
0.2119
0.24452 (15)
0.1982
0.19928 (18)
0.1363
0.24518 (15)
0.80906 (17)
0.8801
0.24053 (15)
0.77351 (18)
0.8203
0.2183 (2)
0.2035
0.31041 (17)
0.39894 (16)
0.4729
0.87706 (17)
0.9947
0.37853 (16)
0.4400
0.25690 (18)
0.2681
0.34316 (15)
0.3069
0.18097 (17)
0.1059
0.2350 (2)
0.2311
0.4486 (2)
0.4262
0.5585
0.78040 (4)
0.74971 (5)
0.7369
0.69692 (5)
0.91374 (5)
0.9272
0.74877 (5)
0.7625
0.62375 (5)
0.6081
0.86402 (5)
0.78637 (5)
0.7987
0.83209 (5)
0.75011 (5)
0.7377
0.94308 (5)
0.9767
0.59743 (5)
0.62069 (5)
0.6031
0.76868 (5)
0.7692
0.66989 (4)
0.6854
0.87438 (5)
0.8611
0.76700 (4)
0.7333
0.67222 (5)
0.6896
0.92305 (5)
0.9433
0.52261 (5)
0.5222
0.5370
0.0175 (2)
0.0228 (3)
0.027*
0.0194 (3)
0.0244 (3)
0.029*
0.0192 (3)
0.023*
0.0274 (3)
0.033*
0.0196 (3)
0.0267 (3)
0.032*
0.0191 (3)
0.0279 (3)
0.034*
0.0305 (3)
0.037*
0.0223 (3)
0.0200 (3)
0.024*
0.0292 (3)
0.035*
0.0195 (3)
0.023*
0.0252 (3)
0.030*
0.0166 (2)
0.020*
0.0248 (3)
0.030*
0.0310 (3)
0.037*
0.0298 (3)
0.045*
0.045*
0.3487
0.4473
0.4897
0.045*
0.22635 (4)
0.07332 (4)
0.01585 (4)
0.12093 (5)
0.22422 (5)
0.17574 (5)
0.1788
0.13695 (5)
0.1035
0.07469 (5)
0.0438
0.40047 (11)
0.32928 (14)
0.29424 (13)
0.39015 (15)
0.40593 (15)
0.46126 (15)
0.4219
0.75279 (16)
0.7045
0.34220 (15)
0.3011
0.13133 (3)
0.18334 (3)
−0.11462 (3)
0.11531 (4)
0.17964 (5)
0.10066 (4)
0.0673
0.11604 (5)
0.1263
0.08504 (5)
0.1006
0.01906 (19)
0.0316 (2)
0.0294 (2)
0.0186 (3)
0.0193 (3)
0.0175 (2)
0.021*
0.0208 (3)
0.025*
0.0199 (3)
0.024*
Acta Cryst. (2020). C76
sup-16

supporting information
C64
C66
H66
C75
H75
C65
C74
H74
C73
H73
C78
C71
C69
H69
C83
H83
C79
H79
C72
H72
C82
H82
C80
H80
C68
H68
C811
H81A
H81B
H81C
C67
H67
C81
0.11821 (5)
0.17394 (6)
0.1391
0.14402 (6)
0.1153
0.17270 (5)
0.19253 (6)
0.1972
0.23435 (6)
0.2676
0.06315 (5)
0.17897 (5)
0.27641 (6)
0.3115
0.01889 (6)
−0.0016
0.09117 (6)
0.1207
0.22748 (5)
0.2560
0.00403 (6)
−0.0259
0.07665 (6)
0.0964
0.27653 (6)
0.3120
0.04246 (6)
0.0339
0.0275
0.0842
0.22546 (6)
0.2262
0.03315 (6)
0.36726 (16)
0.38554 (17)
0.3727
0.92594 (17)
0.9953
0.38931 (15)
0.99728 (16)
1.1152
0.89628 (17)
0.9450
0.34154 (16)
0.65101 (15)
0.41947 (19)
0.4303
0.23595 (17)
0.1715
0.43776 (16)
0.5129
0.72430 (16)
0.6555
0.22232 (18)
0.1487
0.42563 (17)
0.4915
0.4169 (2)
0.4266
0.3967 (2)
0.5144
0.3661
0.3794
0.4003 (2)
0.3993
0.31704 (17)
0.16759 (5)
0.24932 (5)
0.2631
0.11667 (5)
0.1275
0.19937 (5)
0.10159 (5)
0.1023
0.08536 (5)
0.0748
0.03287 (5)
0.10037 (4)
0.20914 (5)
0.1956
0.01259 (5)
0.0333
0.00123 (5)
0.0137
0.08461 (5)
0.0733
−0.03621 (5)
−0.0488
−0.04811 (5)
−0.0689
0.25813 (5)
0.2784
−0.14750 (5)
−0.1420
−0.1805
−0.1425
0.27861 (5)
0.3125
−0.06707 (5)
0.0207 (3)
0.0242 (3)
0.029*
0.0242 (3)
0.029*
0.0196 (3)
0.0245 (3)
0.029*
0.0237 (3)
0.028*
0.0201 (3)
0.0179 (2)
0.0278 (3)
0.033*
0.0243 (3)
0.029*
0.0226 (3)
0.027*
0.0208 (3)
0.025*
0.0261 (3)
0.031*
0.0239 (3)
0.029*
0.0343 (3)
0.041*
0.0337 (3)
0.051*
0.051*
0.051*
0.0314 (3)
0.038*
0.0228 (3)
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
O1
O4
O3
C5
C4
C6
0.0148 (4)
0.0196 (5)
0.0321 (5)
0.0205 (6)
0.0195 (6)
0.0235 (7)
0.0180 (6)
0.0172 (6)
0.0230 (6)
0.0177 (6)
0.0160 (6)
0.0201 (4)
0.0398 (6)
0.0350 (5)
0.0170 (6)
0.0168 (6)
0.0295 (7)
0.0133 (5)
0.0157 (6)
0.0228 (6)
0.0333 (7)
0.0176 (6)
0.0181 (4)
0.0227 (5)
0.0194 (5)
0.0211 (6)
0.0212 (6)
0.0221 (7)
0.0202 (6)
0.0233 (6)
0.0194 (6)
0.0248 (7)
0.0220 (6)
−0.0028 (3)
0.0045 (4)
0.0056 (4)
−0.0014 (5)
−0.0001 (5)
−0.0030 (5)
−0.0011 (5)
0.0006 (5)
−0.0039 (5)
−0.0030 (5)
−0.0002 (5)
0.0019 (3)
0.0063 (4)
−0.0023 (4)
0.0033 (5)
0.0048 (5)
0.0051 (5)
0.0034 (5)
0.0044 (5)
−0.0017 (5)
0.0024 (5)
0.0005 (5)
−0.0018 (3)
0.0012 (4)
0.0010 (4)
0.0018 (5)
0.0024 (5)
0.0015 (5)
0.0006 (5)
−0.0010 (5)
0.0007 (5)
0.0004 (6)
0.0008 (5)
C3
C17
C21
C9
C19
Acta Cryst. (2020). C76
sup-17

supporting information
C23
C18
C16
C2
C14
C15
C10
C11
C12
C20
C13
C8
0.0195 (6)
0.0165 (6)
0.0197 (6)
0.0148 (6)
0.0316 (7)
0.0235 (7)
0.0217 (6)
0.0176 (6)
0.0201 (6)
0.0193 (6)
0.0285 (7)
0.0233 (7)
0.0219 (6)
0.0299 (7)
0.0318 (7)
0.0153 (4)
0.0194 (5)
0.0219 (6)
0.0304 (5)
0.0184 (6)
0.0234 (6)
0.0181 (6)
0.0210 (6)
0.0162 (6)
0.0236 (7)
0.0180 (6)
0.0226 (6)
0.0201 (6)
0.0361 (8)
0.0195 (6)
0.0283 (7)
0.0293 (7)
0.0211 (6)
0.0183 (6)
0.0411 (8)
0.0163 (6)
0.0175 (6)
0.0152 (6)
0.0209 (6)
0.0218 (7)
0.0240 (7)
0.0178 (4)
0.0210 (5)
0.0277 (5)
0.0205 (6)
0.0220 (6)
0.0179 (6)
0.0209 (6)
0.0241 (6)
0.0175 (6)
0.0207 (6)
0.0172 (6)
0.0158 (6)
0.0224 (7)
0.0161 (6)
0.0180 (6)
0.0197 (6)
0.0198 (6)
0.0195 (6)
0.0474 (9)
0.0256 (7)
0.0441 (8)
0.0444 (9)
0.0193 (4)
0.0377 (5)
0.0154 (6)
0.0389 (6)
0.0182 (6)
0.0201 (6)
0.0141 (5)
0.0219 (6)
0.0197 (6)
0.0304 (7)
0.0168 (6)
0.0297 (7)
0.0176 (6)
0.0201 (6)
0.0165 (6)
0.0238 (7)
0.0443 (9)
0.0243 (6)
0.0192 (6)
0.0171 (6)
0.0193 (6)
0.0325 (7)
0.0178 (6)
0.0265 (7)
0.0453 (9)
0.0426 (8)
0.0199 (4)
0.0501 (6)
0.0389 (6)
0.0139 (5)
0.0153 (6)
0.0175 (6)
0.0213 (6)
0.0246 (7)
0.0232 (6)
0.0238 (6)
0.0160 (6)
0.0265 (7)
0.0290 (7)
0.0178 (6)
0.0153 (6)
0.0180 (6)
0.0217 (6)
0.0221 (6)
0.0232 (7)
0.0266 (7)
0.0177 (6)
0.0197 (7)
0.0186 (4)
0.0231 (5)
0.0185 (6)
0.0217 (5)
0.0147 (5)
0.0184 (6)
0.0206 (6)
0.0251 (6)
0.0222 (6)
0.0201 (6)
0.0235 (6)
0.0283 (7)
0.0214 (6)
0.0227 (7)
0.0219 (6)
0.0303 (7)
0.0177 (6)
0.0206 (6)
0.0227 (6)
0.0266 (7)
0.0222 (6)
0.0258 (7)
0.0167 (6)
0.0264 (7)
0.0245 (7)
0.0220 (7)
0.0201 (4)
0.0242 (5)
0.0208 (5)
0.0219 (6)
0.0210 (6)
0.0173 (6)
0.0202 (6)
0.0034 (5)
−0.0020 (5)
−0.0002 (5)
−0.0009 (5)
0.0016 (5)
0.0047 (5)
−0.0021 (5)
0.0010 (5)
−0.0013 (5)
−0.0024 (5)
−0.0040 (5)
−0.0053 (6)
0.0052 (5)
−0.0063 (6)
0.0020 (7)
0.0028 (3)
−0.0037 (4)
0.0019 (5)
−0.0076 (4)
−0.0008 (5)
0.0018 (5)
0.0010 (5)
−0.0016 (5)
0.0006 (5)
0.0027 (5)
−0.0008 (5)
−0.0068 (6)
0.0006 (5)
0.0062 (6)
0.0004 (5)
−0.0072 (6)
0.0058 (6)
0.0031 (5)
0.0018 (5)
−0.0035 (6)
0.0001 (5)
0.0033 (5)
0.0011 (5)
−0.0045 (5)
0.0047 (6)
−0.0002 (6)
0.0030 (3)
−0.0092 (4)
−0.0022 (4)
0.0001 (5)
0.0019 (5)
0.0008 (5)
−0.0002 (5)
0.0005 (5)
0.0008 (5)
0.0029 (5)
−0.0002 (4)
−0.0029 (5)
0.0012 (5)
0.0035 (5)
−0.0016 (4)
0.0009 (5)
0.0032 (5)
0.0005 (5)
−0.0024 (5)
−0.0023 (5)
0.0013 (5)
0.0012 (5)
0.0028 (3)
0.0069 (4)
0.0035 (5)
−0.0052 (4)
−0.0018 (4)
−0.0002 (5)
0.0043 (5)
0.0013 (5)
0.0020 (5)
0.0059 (5)
0.0050 (5)
−0.0029 (5)
0.0038 (5)
−0.0013 (5)
0.0049 (5)
−0.0014 (5)
0.0022 (5)
−0.0010 (5)
0.0034 (5)
−0.0065 (6)
0.0003 (5)
0.0033 (5)
0.0015 (4)
0.0001 (5)
−0.0023 (5)
0.0003 (5)
0.0051 (3)
0.0054 (4)
−0.0005 (4)
0.0044 (5)
0.0041 (5)
0.0028 (4)
0.0027 (5)
−0.0023 (5)
0.0004 (5)
−0.0011 (5)
−0.0001 (4)
−0.0006 (5)
−0.0035 (5)
0.0015 (5)
0.0001 (5)
−0.0004 (5)
−0.0008 (5)
0.0023 (5)
0.0018 (6)
0.0013 (5)
0.0012 (6)
−0.0018 (6)
0.0012 (3)
0.0002 (4)
−0.0017 (5)
0.0028 (4)
−0.0005 (5)
−0.0004 (5)
−0.0014 (5)
0.0010 (5)
−0.0019 (5)
−0.0010 (5)
−0.0006 (5)
−0.0007 (6)
−0.0014 (5)
−0.0021 (5)
−0.0029 (5)
0.0051 (6)
−0.0009 (6)
−0.0014 (5)
0.0006 (5)
0.0005 (5)
−0.0021 (5)
−0.0013 (6)
−0.0003 (5)
0.0027 (5)
−0.0015 (6)
0.0053 (6)
0.0015 (3)
0.0043 (5)
−0.0014 (4)
0.0010 (5)
0.0010 (5)
0.0006 (5)
0.0004 (5)
C22
C7
C211
O31
O34
C40
O33
C41
C42
C33
C46
C48
C36
C47
C52
C35
C43
C34
C45
C37
C51
C50
C44
C49
C39
C32
C53
C38
C511
O61
O64
O63
C63
C70
C62
C76
Acta Cryst. (2020). C76
sup-18

supporting information
C77
C64
C66
C75
C65
C74
C73
C78
C71
C69
C83
C79
C72
C82
C80
C68
C811
C67
C81
0.0193 (6)
0.0211 (6)
0.0224 (6)
0.0281 (7)
0.0203 (6)
0.0316 (7)
0.0230 (6)
0.0186 (6)
0.0200 (6)
0.0188 (6)
0.0206 (6)
0.0235 (6)
0.0202 (6)
0.0215 (6)
0.0247 (7)
0.0210 (7)
0.0291 (7)
0.0279 (7)
0.0220 (6)
0.0175 (6)
0.0191 (6)
0.0279 (7)
0.0203 (6)
0.0160 (6)
0.0157 (6)
0.0218 (6)
0.0176 (6)
0.0179 (6)
0.0368 (8)
0.0253 (7)
0.0193 (6)
0.0207 (6)
0.0286 (7)
0.0233 (6)
0.0527 (10)
0.0505 (9)
0.0454 (8)
0.0243 (6)
0.0235 (6)
0.0224 (6)
0.0233 (7)
0.0237 (6)
0.0228 (6)
0.0243 (6)
0.0255 (7)
0.0239 (6)
0.0151 (6)
0.0280 (7)
0.0267 (7)
0.0243 (6)
0.0215 (6)
0.0269 (7)
0.0237 (7)
0.0277 (7)
0.0214 (7)
0.0208 (7)
0.0215 (6)
−0.0004 (5)
−0.0015 (5)
−0.0007 (5)
0.0050 (5)
0.0004 (5)
−0.0016 (5)
−0.0058 (5)
0.0016 (5)
−0.0019 (5)
0.0006 (6)
−0.0034 (5)
−0.0030 (5)
−0.0003 (5)
−0.0043 (5)
−0.0010 (5)
−0.0027 (6)
−0.0002 (7)
−0.0024 (6)
0.0043 (5)
0.0051 (5)
0.0049 (5)
0.0061 (5)
0.0015 (5)
0.0040 (5)
−0.0041 (5)
−0.0009 (5)
0.0025 (5)
0.0001 (4)
0.0038 (5)
0.0020 (5)
0.0008 (5)
0.0022 (5)
−0.0021 (5)
0.0033 (5)
−0.0026 (5)
0.0030 (5)
0.0020 (5)
0.0000 (5)
0.0012 (5)
0.0011 (5)
0.0029 (5)
−0.0017 (5)
0.0013 (5)
0.0006 (5)
0.0038 (5)
−0.0003 (5)
0.0003 (5)
0.0043 (6)
0.0033 (5)
0.0006 (5)
0.0007 (5)
−0.0007 (6)
0.0027 (5)
0.0051 (7)
0.0030 (6)
0.0048 (6)
−0.0004 (5)
Geometric parameters (Å, º)
O1—C10
O1—C2
O4—C4
O3—C21
O3—C211
C5—C10
C5—C6
C5—C4
C4—C3
C6—C7
C6—H6
1.3623 (15)
C52—C53
1.374 (2)
1.398 (2)
0.9500
1.4730 (17)
1.383 (2)
0.9500
1.391 (2)
0.9500
1.400 (2)
0.9500
1.3959 (18)
1.3952 (18)
0.9500
0.9500
0.9500
1.379 (2)
0.9500
1.0000
0.9500
0.9500
0.9800
0.9800
1.4600 (14)
1.2287 (16)
1.3565 (16)
1.4308 (18)
1.4000 (18)
1.4038 (19)
1.4717 (17)
1.4941 (17)
1.3786 (19)
0.9500
1.3451 (18)
1.5052 (16)
1.4597 (18)
0.9500
1.395 (2)
1.3983 (18)
1.383 (2)
1.3923 (18)
0.9500
1.3919 (18)
1.4007 (18)
0.9500
1.3778 (19)
1.4082 (18)
0.9500
C52—C51
C52—H52
C35—C34
C43—C44
C43—H43
C45—C44
C45—H45
C37—C38
C37—H37
C51—C50
C50—C49
C50—H50
C44—H44
C49—H49
C39—C38
C39—H39
C32—H32
C53—H53
C38—H38
C511—H51A
C511—H51B
C511—H51C
O61—C70
O61—C62
O64—C64
C3—C17
C3—C2
C17—C18
C17—H17
C21—C22
C21—C20
C9—C8
C9—C10
C9—H9
C19—C20
C19—C18
C19—H19
C23—C22
C23—C18
C23—H23
0.9800
1.3656 (16)
1.4592 (14)
1.2284 (16)
Acta Cryst. (2020). C76
sup-19