Hydrogen-bonded dimers in 3-amino-4-anilino-1H-isochromen-1-one and a hydrogen-bonded sheet in 3-amino-4-[methyl(phenyl)amino]-1H-isochromen-1-one

Article abstract of DOI:10.1107/S0108270113014777

The molecules of 3-amino-4-anilino-1H-isochromen-1-one, C ₁₅H₁₂N₂O₂, (I), and 3-amino-4-[methyl(phenyl)amino]-1H-isochromen-1-one, C₁₆H ₁₄N₂O₂, (II), adopt very similar conformations, with the substituted amino group PhNR, where R = H in (I) and R = Me in (II), almost orthogonal to the adjacent heterocyclic ring. The molecules of (I) are linked into cyclic centrosymmetric dimers by pairs of N - H...O hydrogen bonds, while those of (II) are linked into complex sheets by a combination of one three-centre N - H...(O)₂ hydrogen bond, one two-centre C - H...O hydrogen bond and two C - H...π(arene) hydrogen bonds.

Full text of DOI:10.1107/S0108270113014777

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
group accommodates equal numbers of the two conforma-
tional enantiomers in each case. The conformational similarity
of the two compounds is also shown by the dihedral angles
between the planes of their two aryl rings, viz. 79.2 (2)ꢁ in (I)
and 79.3 (2)ꢁ in (II). In both compounds, the fused aryl rings
show evidence of some bond fixation, with the C5—C6 and
C7—C8 bonds being significantly shorter than the other bonds
in these rings (Tables 1 and 3). The rotation of the substituted
amino group by almost 90ꢁ from the plane of the adjacent
heterocyclic ring, presumably for steric reasons, effectively
prevents the development of any electronic polarization
involving significant transfer of electron density from atom
N1, via atoms C4, C4a, C8 and C1, to atom O11.
ISSN 0108-2701
Hydrogen-bonded dimers in
3-amino-4-anilino-1H-isochromen-1-
one and a hydrogen-bonded sheet in
3-amino-4-[methyl(phenyl)amino]-
1H-isochromen-1-one
a
a
b
´
Daniel E. Vicentes, Ricaurte Rodrıguez, Justo Cobo and
Christopher Glidewellc*
a
´
Department of Chemistry, Universidad Nacional de Colombia, Bogota AA 14490,
b
´
´
´
´
Colombia, Departamento de Quımica Inorganica y Organica, Universidad de Jaen,
23071 Jaen, Spain, and cSchool of Chemistry, University of St Andrews, Fife
´
KY16 9ST, Scotland
Correspondence e-mail: cg@st-andrews.ac.uk
Received 9 May 2013
Accepted 29 May 2013
In both compounds, there is a short intramolecular N—
Hꢀ ꢀ ꢀN contact but, in each case, the N—Hꢀ ꢀ ꢀN angle is small
(Tables 2 and 4). Atom N41 is only slightly pyramidalized, with
the sums of the bond angles being 353.3ꢁ in (I) and 356.5 (3)ꢁ
in (II) (cf. 328.4ꢁ for an idealized pyramidal geometry). Hence,
atom N41 is likely to be of low basicity in each compound, so
these contacts must be regarded as adventitious rather than
significant.
The molecules of 3-amino-4-anilino-1H-isochromen-1-one,
C15H12N2O2, (I), and 3-amino-4-[methyl(phenyl)amino]-1H-
isochromen-1-one, C16H14N2O2, (II), adopt very similar
conformations, with the substituted amino group PhNR, where
R = H in (I) and R = Me in (II), almost orthogonal to the
adjacent heterocyclic ring. The molecules of (I) are linked into
cyclic centrosymmetric dimers by pairs of N—Hꢀ ꢀ ꢀO
hydrogen bonds, while those of (II) are linked into complex
sheets by a combination of one three-centre N—Hꢀ ꢀ ꢀ(O)2
hydrogen bond, one two-centre C—Hꢀ ꢀ ꢀO hydrogen bond
and two C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bonds.
Comment
Isochromen-1-ones are a class of compounds which exhibit a
wide range of biological activities, including fungicidal
(Findlay & Buthelezi, 1995), herbicidal and insecticidal
(Qadeer, Rama et al., 2007), antibacterial (Zhang et al., 2008),
anti-inflammatory (Qadeer, Rama & Gardun˜o, 2007) and
antitumour (Lam et al., 1989) activities. As part of a
programme aimed at the production of new heterocyclic
compounds containing an isochromene fragment, we have
synthesized several 3,4-diamino derivatives using the method-
ology of Opatz & Ferenc (2005), and we report here the
molecular and supramolecular structures of 3-amino-4-
anilino-1H-isochromen-1-one, (I) (Fig. 1), and 3-amino-4-
[methyl(phenyl)amino]-1H-isochromen-1-one, (II) (Fig. 2).
The molecular conformations of (I) and (II) are very
similar, as shown by the key torsion angles (Tables 1 and 3).
These values also show that the molecules of (I) and (II)
exhibit no internal symmetry and hence that they are
conformationally chiral, although the centrosymmetric space
Figure 1
The molecular structure of (I), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level.
770 # 2013 International Union of Crystallography
doi:10.1107/S0108270113014777
Acta Cryst. (2013). C69, 770–773

organic compounds
structure of (I), two short C—Hꢀ ꢀ ꢀꢀ(arene) contacts are
present, although in each of these the C—Hꢀ ꢀ ꢀCg (where Cg is
the ring centroid) angle is less than 140ꢁ and thus they are not
regarded as structurally significant (cf. Wood et al., 2009). The
only short intermolecular contacts to potential hydrogen-bond
acceptors are made by atom H41, bonded to N41. Both have
Hꢀ ꢀ ꢀO distances (Table 2) greater than the sum of the van der
Waals radii (Bondi, 1964) and hence these contacts cannot be
regarded as either hydrogen bonds or having structural
significance.
Compound (II) has fewer N—H bonds in its molecular
constitution than (I), despite the fact that the overall supra-
molecular assembly for (II) is more complex than that for (I),
as N—Hꢀ ꢀ ꢀO, C—Hꢀ ꢀ ꢀO and C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen
bonds are all present (Table 4). Together, these interactions
link the molecules into complex sheets, and a cyclic centro-
symmetric dimer can be regarded as the basic building block
for the formation of this sheet. The dimer in (II) differs from
that in (I) in that it contains three-centre N—Hꢀ ꢀ ꢀ(O)2
hydrogen bonds, as opposed to the simple two-centre N—
Hꢀ ꢀ ꢀO hydrogen bonds in the dimer of (I). Inversion-related
pairs of three-centre hydrogen bonds generate a dimer in
which an outer R22(12) ring is divided into one R22(8) segment
and two R21(4) segments (Fig. 4). The reference dimer is
Figure 2
The molecular structure of (II), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level.
1
1
Although there are three independent N—H bonds in the
molecule of (I), only one of these participates in the supra-
molecular assembly. Pairs of inversion-related N—Hꢀ ꢀ ꢀO
hydrogen bonds (Table 2) link pairs of molecules into cyclic
centrosymmetric R22(12) (Bernstein et al., 1995) dimers (Fig. 3).
While C—Hꢀ ꢀ ꢀO hydrogen bonds are absent from the crystal
centred at (12, , ) and the single C—Hꢀ ꢀ ꢀO hydrogen bond
2
2
suffices to link dimers of this type into a sheet. In the reference
dimer, atoms C46 at (x, y, z) and (ꢂx + 1, ꢂy + 1, ꢂz + 1) act
as hydrogen-bond donors to, respectively, atoms O11 at
1
2
1
2
(ꢂx + 1, y ꢂ , ꢂz + 32) and (x, ꢂy + 32, z ꢂ ), which form parts
Figure 3
Figure 4
Part of the crystal structure of (I), showing the formation of the
hydrogen-bonded dimer. For the sake of clarity, H atoms bonded to C
atoms and the unit-cell outline have been omitted. Atoms marked with an
asterisk (*) are at the symmetry position (ꢂx + 1, ꢂy, ꢂz + 1). Dashed
lines indicate hydrogen bonds.
Part of the crystal structure of (II), showing the formation of the
hydrogen-bonded dimer. For the sake of clarity, H atoms bonded to C
atoms and the unit-cell outline have been omitted. Atoms marked with an
asterisk (*) are at the symmetry position (ꢂx + 1, ꢂy + 1, ꢂz + 1). Dashed
lines indicate hydrogen bonds.
ꢃ
Acta Cryst. (2013). C69, 770–773
Vicentes et al. C15H12N2O2 and C16H14N2O2 771

organic compounds
Table 2
Hydrogen-bond geometry (A, ) for (I).
ꢁ
˚
Cg2 represents the centroid of the C4a/C5–C8/C8a ring and Cg3 represents the
centroid of the C61–C66 ring.
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
N31—H31Aꢀ ꢀ ꢀO11i
N31—H31Bꢀ ꢀ ꢀN41
N41—H41ꢀ ꢀ ꢀO2ii
N41—H41ꢀ ꢀ ꢀO11iii
C6—H6ꢀ ꢀ ꢀCg2iv
0.86
0.86
0.88
0.88
0.95
0.95
2.09
2.55
2.79
2.82
2.88
2.98
2.941 (2)
2.852 (2)
3.503 (2)
3.465 (2)
3.579 (2)
3.719 (2)
169
102
140
131
131
135
C7—H7ꢀ ꢀ ꢀCg3v
Symmetry codes: (i) ꢂx þ 1; ꢂy; ꢂz þ 1; (ii) x; y þ 1; z; (iii) ꢂx þ 1; ꢂy þ 1; ꢂz þ 1;
1
2
3
2
1
2
3
2
(iv) ꢂx þ 1; y þ ; ꢂz þ ; (v) ꢂx þ 1; y ꢂ ; ꢂz þ .
Table 3
Selected geometric parameters (A, ) for (II).
Figure 5
ꢁ
˚
A stereoview of part of the crystal structure of (II), showing the
formation of the hydrogen-bonded sheet parallel to (100). For the sake of
clarity, H atoms not involved in the motifs shown have been omitted.
Dashed lines indicate hydrogen bonds.
C4a—C5
C5—C6
C6—C7
1.411 (2)
1.374 (3)
1.400 (3)
C7—C8
C8—C8a
C8a—C4a
1.374 (3)
1.402 (3)
1.413 (2)
of the cyclic dimers centred at (12, 0, 1) and (21, 1, 0), respec-
tively. Atoms O11 at (x, y, z) and (ꢂx + 1, ꢂy + 1, ꢂz + 1)
accept hydrogen bonds from, respectively, atoms C46 at
C3—C4—N41—C41
C3—C4—N41—C47
108.4 (2)
ꢂ92.6 (2)
C4—N41—C41—C42
165.59 (17)
1
(ꢂx + 1, y + 12, ꢂz + 23) and (x, ꢂy + 12, z ꢂ ), which form parts
2
m.p. 448–450 K; MS (EI, 70 eV) m/z (%): 252 (100), 235 (16), 223 (26),
196 (52), 195 (71), 180 (66), 179 (81), 178 (68), 152 (26), 151 (24),
130 (40), 77 (85). Analysis for (II): yield 92%, m.p. 476–478 K; MS
(EI, 70 eV) m/z (%): 266 (100), 249 (53), 238 (62), 223 (52), 210 (38),
194 (74), 180 (25), 179 (25), 165 (28), 152 (23), 130 (23), 77 (56).
of the dimers centred at (21, 1, 1) and (12, 0, 0), respectively. In
this manner, the cyclic dimers are linked into a sheet lying
parallel to (100) (Fig. 5). There are also two structurally
significant C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bonds present
(Table 4), but these both lie within the sheet and hence do not
affect the dimensionality of the hydrogen-bonded structure,
but simply add to its complexity.
Compound (I)
Thus, the notional change from the constitution of (I) to
that of (II) by the introduction of a single methyl group brings
about a significant change in the pattern of supramolecular
assembly, even though neither the methyl group in (II), nor
the corresponding N—H bond in (I), plays any direct role in
the assembly.
Crystal data
3
˚
C15H12N2O2
Mr = 252.27
Monoclinic, P21=c
a = 10.157 (2) A
b = 5.7147 (5) A
V = 1188.8 (3) A
Z = 4
Mo Kꢂ radiation
ꢃ = 0.10 mmꢂ1
T = 120 K
0.28 ꢄ 0.19 ꢄ 0.16 mm
˚
˚
˚
c = 21.208 (3) A
ꢁ = 105.048 (15)ꢁ
Experimental
Data collection
Bruker–Nonius KappaCCD area-
detector diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.974, Tmax = 0.985
20238 measured reflections
2735 independent reflections
1921 reflections with I > 2ꢄ(I)
Rint = 0.061
For the synthesis of (I) and (II), acetic acid (1.14 ml, 20 mmol), either
aniline [for (I)] or N-methylaniline [for (II)] (20 mmol) and potas-
sium cyanide (0.78 g, 12 mmol) were added to a stirred solution of
2-formylbenzoic acid (10 mmol) in methanol (25 ml). The resulting
mixture was heated under reflux for 3 h. After cooling the mixture to
ambient temperature, the resulting crystalline product was collected
by filtration, washed successively with water and cold methanol, and
then dried in air. Yellow crystals suitable for single-crystal X-ray
diffraction were grown by slow evaporation, at ambient temperature
and in air, from solutions in methanol. Analysis for (I): yield 86%,
Refinement
R[F2 > 2ꢄ(F2)] = 0.047
wR(F2) = 0.113
S = 1.10
172 parameters
H-atom parameteꢂrs3 constrained
˚
Áꢅmax = 0.20 e A
Áꢅmin = ꢂ0.32 e A
ꢂ3
˚
2735 reflections
Compound (II)
Table 1
Selected geometric parameters (A, ) for (I).
ꢁ
˚
Crystal data
3
˚
V = 1303.1 (3) A
Z = 4
C16H14N2O2
Mr = 266.29
C4a—C5
C5—C6
C6—C7
1.410 (2)
1.379 (3)
1.400 (3)
C7—C8
C8—C8a
C8a—C4a
1.378 (3)
1.403 (2)
1.413 (2)
Monoclinic, P21=c
Mo Kꢂ radiation
ꢃ = 0.09 mmꢂ1
T = 120 K
0.32 ꢄ 0.30 ꢄ 0.17 mm
˚
a = 14.5018 (15) A
˚
b = 7.7796 (8) A
˚
c = 11.608 (2) A
C3—C4—N41—C41
112.61 (18)
C4—N41—C41—C42
160.47 (15)
ꢁ = 95.728 (13)ꢁ
ꢃ
772 Vicentes et al.
C15H12N2O2 and C16H14N2O2
Acta Cryst. (2013). C69, 770–773

organic compounds
Table 4
Hydrogen-bond geometry (A, ) for (II).
structure: SIR2004 (Burla et al., 2005); program(s) used to refine
structure: SHELXL97 (Sheldrick, 2008); molecular graphics:
PLATON (Spek, 2009); software used to prepare material for
publication: SHELXL97 and PLATON.
ꢁ
˚
Cg2 represents the centroid of the C4a/C5–C8/C8a ring and Cg3 represents the
centroid of the C61–C66 ring.
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
´
´
The authors thank the Centro de Instrumentacion Cientı-
N31—H31Aꢀ ꢀ ꢀO2i
N31—H31Aꢀ ꢀ ꢀO11i
N31—H31Bꢀ ꢀ ꢀN41
C46—H46ꢀ ꢀ ꢀO11ii
C6—H6ꢀ ꢀ ꢀCg3iii
0.88
0.88
0.88
0.95
0.95
0.95
2.58
2.20
2.51
2.48
2.62
2.69
3.395 (2)
3.011 (2)
2.841 (2)
3.404 (2)
3.449 (2)
3.571 (2)
154
152
103
164
146
155
fico-Tecnica of the Universidad de Jaen and the staff for the
data collection. DV and RR thank the Universidad Nacional
´
´
´
´
de Colombia for financial support. JC thanks the Consejerıa
´
de Innovacion, Ciencia y Empresa (Junta de Andalucıa,
Spain) and the Universidad de Jaen for financial support.
C45—H45ꢀ ꢀ ꢀCg2iv
´
1
2
3
2
1
2
Symmetry codes: (i) ꢂx þ 1; ꢂy þ 1; ꢂz þ 1; (ii) ꢂx þ 1; y ꢂ ; ꢂz þ ; (iii) x; ꢂy þ ,
1
2
z þ ; (iv) x; y ꢂ 1; z.
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: YF3035). Services for accessing these data are
described at the back of the journal.
Data collection
Bruker–Nonius KappaCCD area-
detector diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.971, Tmax = 0.985
21810 measured reflections
2987 independent reflections
1958 reflections with I > 2ꢄ(I)
Rint = 0.061
References
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.
Int. Ed. Engl. 34, 1555–1573.
Bondi, A. (1964). J. Phys. Chem. 68, 441–451.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De
Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38,
381–388.
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000).
J. Appl. Cryst. 33, 893–898.
Refinement
R[F2 > 2ꢄ(F2)] = 0.050
wR(F2) = 0.125
S = 1.07
182 parameters
H-atom parameteꢂrs3 constrained
˚
Áꢅmax = 0.22 e A
ꢂ3
˚
2987 reflections
Áꢅmin = ꢂ0.29 e A
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003).
J. Appl. Cryst. 36, 220–229.
Findlay, J. & Buthelezi, S. (1995). J. Nat. Prod. 58, 1759–1766.
Lam, K., Veitch, J., Forenza, S., Combs, C. & Colson, K. (1989). J. Nat. Prod.
52, 1015–1021.
All H atoms were located in difference maps. C-bound H atoms
were treated as riding in geometrically idealized positions, with
˚
C—H = 0.95 (aromatic) or 0.98 A (methyl) and with Uiso(H) =
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Opatz, T. & Ferenc, D. (2005). Eur. J. Org. Chem. 5, 817–821.
Qadeer, G., Rama, N., Fan, Z., Liu, B. & Liu, X. (2007). J. Braz. Chem. Soc. 18,
1176–1182.
kUeq(C), where k = 1.5 for the methyl group, which was permitted to
rotate but not to tilt, and 1.2 for all other C-bound H atoms. N-bound
H atoms were permitted to ride at the positions located in difference
maps, with Uiso(H) = 1.2Ueq(N), giving the N—H distances shown in
Tables 2 and 4.
Qadeer, G., Rama, N. & Gardun˜o, M. (2007). J. Fluorine Chem. 128, 641–646.
¨
Sheldrick, G. M. (2003). SADABS. University of Gottingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Wood, P. A., Allen, F. H. & Pidcock, E. (2009). CrystEngComm, 11, 1563–1571.
Zhang, W., Krohn, K., Draeger, S. & Schulz, B. (2008). J. Nat. Prod. 71, 1078–
1081.
For both compounds, data collection: COLLECT (Nonius, 1998);
cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduc-
tion: EVALCCD (Duisenberg et al., 2003); program(s) used to solve
ꢃ
Acta Cryst. (2013). C69, 770–773
Vicentes et al. C15H12N2O2 and C16H14N2O2 773

supplementary materials
supplementary materials
Acta Cryst. (2013). C69, 770-773 [doi:10.1107/S0108270113014777]
Hydrogen-bonded dimers in 3-amino-4-anilino-1H-isochromen-1-one and a
hydrogen-bonded sheet in 3-amino-4-[methyl(phenyl)amino]-1H-isochromen-1-
one
Daniel E. Vicentes, Ricaurte Rodríguez, Justo Cobo and Christopher Glidewell
Computing details
For both compounds, data collection: COLLECT (Nonius, 1998); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000);
data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR2004 (Burla et al., 2005);
program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software
used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
(I) 3-Amino-4-anilino-1H-isochromen-1-one
Crystal data
C15H12N2O2
Mr = 252.27
F(000) = 528
Dx = 1.410 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 2735 reflections
θ = 3.2–27.5°
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 10.157 (2) Å
b = 5.7147 (5) Å
c = 21.208 (3) Å
β = 105.048 (15)°
V = 1188.8 (3) Å3
Z = 4
µ = 0.10 mm−1
T = 120 K
Block, yellow
0.28 × 0.19 × 0.16 mm
Data collection
Bruker Nonius KappaCCD area-detector
diffractometer
Radiation source: Bruker Nonius FR591
rotating anode
Graphite monochromator
Detector resolution: 9.091 pixels mm-1
φ and ω scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.974, Tmax = 0.985
20238 measured reflections
2735 independent reflections
1921 reflections with I > 2σ(I)
Rint = 0.061
θ
max = 27.5°, θmin = 3.2°
h = −13→13
k = −7→7
l = −27→27
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.047
wR(F2) = 0.113
0 restraints
Primary atom site location: structure-invariant
direct methods
Secondary atom site location: difference Fourier
map
S = 1.10
2735 reflections
172 parameters
Hydrogen site location: inferred from
neighbouring sites
Acta Cryst. (2013). C69, 770-773
sup-1

supplementary materials
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0424P)2 + 0.5724P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.20 e Å−3
Δρmin = −0.32 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
C1
0.59062 (17)
0.47584 (12)
0.37270 (17)
0.37494 (17)
0.48515 (17)
0.49359 (18)
0.4248
0.2369 (3)
0.2154 (2)
0.3787 (3)
0.5680 (3)
0.5944 (3)
0.7811 (3)
0.8981
0.59534 (8)
0.54346 (5)
0.53060 (8)
0.56922 (8)
0.62705 (8)
0.67141 (8)
0.6632
0.0221 (4)
0.0236 (3)
0.0217 (4)
0.0212 (4)
0.0211 (4)
0.0233 (4)
0.028*
O2
C3
C4
C4a
C5
H5
C6
0.60091 (19)
0.6051
0.7951 (3)
0.9222
0.72655 (9)
0.7559
0.0271 (4)
0.033*
H6
C7
0.70381 (18)
0.7764
0.6254 (3)
0.6363
0.74013 (9)
0.7787
0.0267 (4)
0.032*
H7
C8
0.69917 (18)
0.7693
0.4423 (3)
0.3277
0.69730 (9)
0.7059
0.0247 (4)
0.030*
H8
C8a
O11
N31
H31A
H31B
N41
H41
C41
C42
H42
C43
H43
C44
H44
C45
H45
C46
H46
0.59052 (17)
0.67983 (13)
0.27422 (16)
0.2944
0.4258 (3)
0.0941 (2)
0.3171 (3)
0.2093
0.64102 (8)
0.59781 (6)
0.47708 (7)
0.4528
0.0213 (4)
0.0289 (3)
0.0291 (4)
0.035*
0.2076
0.4131
0.4636
0.035*
0.26697 (15)
0.2832
0.7334 (3)
0.8578
0.55028 (7)
0.5290
0.0230 (3)
0.028*
0.17127 (17)
0.09466 (18)
0.1104
0.7663 (3)
0.9726 (3)
1.0919
0.58681 (8)
0.57911 (8)
0.5507
0.0205 (4)
0.0234 (4)
0.028*
−0.00440 (18)
−0.0569
1.0034 (3)
1.1430
0.61281 (9)
0.6067
0.0259 (4)
0.031*
−0.02781 (18)
−0.0954
0.8330 (3)
0.8553
0.65530 (9)
0.6784
0.0270 (4)
0.032*
0.04934 (18)
0.0346
0.6292 (3)
0.5118
0.66342 (9)
0.6926
0.0263 (4)
0.032*
0.14788 (18)
0.1994
0.5946 (3)
0.4539
0.62942 (8)
0.6352
0.0240 (4)
0.029*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C1
O2
C3
C4
C4a
C5
C6
C7
0.0210 (8)
0.0244 (6)
0.0215 (8)
0.0222 (9)
0.0232 (9)
0.0271 (9)
0.0304 (10)
0.0244 (9)
0.0235 (9)
0.0238 (6)
0.0250 (9)
0.0212 (8)
0.0215 (8)
0.0203 (9)
0.0267 (10)
0.0324 (10)
0.0237 (9)
−0.0036 (7)
0.0012 (5)
0.0091 (7)
0.0069 (5)
0.0089 (7)
0.0089 (7)
0.0099 (7)
0.0105 (7)
0.0103 (8)
0.0047 (7)
−0.0004 (7)
−0.0050 (5)
0.0017 (7)
0.0006 (7)
0.0009 (7)
−0.0018 (7)
−0.0059 (8)
−0.0028 (8)
0.0231 (6)
0.0206 (8)
0.0218 (8)
0.0208 (8)
0.0247 (9)
0.0259 (9)
0.0226 (9)
−0.0001 (7)
−0.0005 (7)
−0.0025 (7)
−0.0005 (7)
−0.0055 (8)
−0.0055 (8)
Acta Cryst. (2013). C69, 770-773
sup-2

supplementary materials
C8
0.0210 (9)
0.0219 (8)
0.0250 (7)
0.0296 (8)
0.0273 (8)
0.0212 (8)
0.0233 (9)
0.0215 (9)
0.0206 (9)
0.0246 (9)
0.0244 (9)
0.0269 (9)
0.0217 (8)
0.0286 (7)
0.0317 (8)
0.0212 (7)
0.0216 (8)
0.0213 (9)
0.0235 (9)
0.0334 (10)
0.0306 (10)
0.0223 (9)
0.0275 (9)
0.0230 (8)
0.0343 (7)
0.0243 (8)
0.0221 (7)
0.0175 (8)
0.0233 (9)
0.0303 (9)
0.0262 (9)
0.0231 (9)
0.0244 (9)
−0.0016 (7)
−0.0023 (7)
0.0049 (6)
0.0036 (7)
0.0036 (6)
−0.0019 (7)
−0.0003 (7)
0.0025 (7)
−0.0015 (8)
−0.0023 (8)
0.0025 (7)
0.0084 (7)
0.0107 (7)
0.0098 (6)
0.0039 (7)
0.0093 (6)
0.0027 (7)
0.0018 (7)
0.0024 (7)
0.0046 (7)
0.0054 (7)
0.0049 (7)
0.0001 (7)
−0.0004 (7)
−0.0056 (6)
−0.0071 (7)
0.0043 (6)
−0.0027 (7)
0.0014 (7)
−0.0023 (8)
−0.0043 (8)
0.0027 (7)
0.0022 (7)
C8a
O11
N31
N41
C41
C42
C43
C44
C45
C46
Geometric parameters (Å, º)
C1—O11
C1—O2
C1—C8a
O2—C3
C3—N31
C3—C4
C4—N41
C4—C4a
C4a—C5
C5—C6
C5—H5
C6—C7
C6—H6
C7—C8
C7—H7
C8—C8a
C8—H8
1.210 (2)
C8a—C4a
1.413 (2)
1.385 (2)
1.450 (2)
1.377 (2)
1.350 (2)
1.354 (2)
1.424 (2)
1.438 (2)
1.410 (2)
1.379 (3)
0.9500
N31—H31A
N31—H31B
N41—C41
N41—H41
C41—C46
C41—C42
C42—C43
C42—H42
C43—C44
C43—H43
C44—C45
C44—H44
C45—C46
C45—H45
C46—H46
0.8604
0.8602
1.404 (2)
0.8800
1.395 (2)
1.399 (2)
1.388 (3)
0.9500
1.389 (3)
0.9500
1.400 (3)
0.9500
1.389 (3)
0.9500
1.378 (3)
0.9500
1.391 (3)
0.9500
1.403 (2)
0.9500
0.9500
O11—C1—O2
O11—C1—C8a
O2—C1—C8a
C3—O2—C1
N31—C3—C4
N31—C3—O2
C4—C3—O2
C3—C4—N41
C3—C4—C4a
N41—C4—C4a
C5—C4a—C8a
C5—C4a—C4
C8a—C4a—C4
C6—C5—C4a
C6—C5—H5
C4a—C5—H5
C5—C6—C7
C5—C6—H6
116.15 (15)
127.09 (16)
116.76 (15)
122.51 (13)
127.56 (16)
110.44 (15)
121.99 (15)
117.98 (15)
119.15 (16)
122.88 (15)
117.67 (16)
123.19 (16)
119.13 (15)
120.50 (17)
119.7
C8—C8a—C1
118.80 (16)
119.94 (15)
116.7
C4a—C8a—C1
C3—N31—H31A
C3—N31—H31B
H31A—N31—H31B
C41—N41—C4
C41—N41—H41
C4—N41—H41
C46—C41—C42
C46—C41—N41
C42—C41—N41
C43—C42—C41
C43—C42—H42
C41—C42—H42
C42—C43—C44
C42—C43—H43
C44—C43—H43
C43—C44—C45
117.4
123.2
121.72 (14)
115.0
116.6
119.03 (16)
121.47 (15)
119.48 (15)
120.15 (16)
119.9
119.9
120.95 (17)
119.5
119.7
121.20 (17)
119.4
119.5
118.84 (17)
Acta Cryst. (2013). C69, 770-773
sup-3

supplementary materials
C7—C6—H6
C8—C7—C6
C8—C7—H7
C6—C7—H7
C7—C8—C8a
C7—C8—H8
C8a—C8—H8
C8—C8a—C4a
119.4
C43—C44—H44
C45—C44—H44
C44—C45—C46
C44—C45—H45
C46—C45—H45
C45—C46—C41
C45—C46—H46
C41—C46—H46
120.6
119.62 (17)
120.2
120.6
120.88 (17)
119.6
120.2
119.79 (17)
120.1
119.6
120.16 (16)
119.9
120.1
121.20 (16)
119.9
O11—C1—O2—C3
C8a—C1—O2—C3
C1—O2—C3—N31
C1—O2—C3—C4
N31—C3—C4—N41
O2—C3—C4—N41
N31—C3—C4—C4a
O2—C3—C4—C4a
C3—C4—C4a—C5
N41—C4—C4a—C5
C3—C4—C4a—C8a
N41—C4—C4a—C8a
C8a—C4a—C5—C6
C4—C4a—C5—C6
C4a—C5—C6—C7
C5—C6—C7—C8
C6—C7—C8—C8a
C7—C8—C8a—C4a
C7—C8—C8a—C1
C5—C4a—C8a—C8
−173.13 (15)
7.4 (2)
C4—C4a—C8a—C8
C5—C4a—C8a—C1
C4—C4a—C8a—C1
O11—C1—C8a—C8
O2—C1—C8a—C8
−179.12 (16)
−176.80 (15)
3.6 (2)
179.26 (14)
−2.1 (2)
−4.8 (3)
−4.6 (3)
174.57 (15)
172.58 (17)
−8.1 (2)
177.02 (14)
175.57 (17)
−2.8 (2)
O11—C1—C8a—C4a
O2—C1—C8a—C4a
C3—C4—N41—C41
C4a—C4—N41—C41
C4—N41—C41—C46
C4—N41—C41—C42
C46—C41—C42—C43
N41—C41—C42—C43
C41—C42—C43—C44
C42—C43—C44—C45
C43—C44—C45—C46
C44—C45—C46—C41
C42—C41—C46—C45
N41—C41—C46—C45
112.61 (18)
−67.5 (2)
−21.4 (2)
160.47 (15)
−0.9 (2)
−177.66 (16)
2.5 (3)
1.9 (2)
−177.92 (15)
−0.5 (2)
177.27 (15)
1.0 (3)
179.06 (17)
−0.1 (3)
−0.3 (3)
0.9 (3)
−0.4 (3)
−0.9 (3)
0.5 (3)
0.2 (3)
0.2 (2)
177.56 (16)
0.5 (2)
−177.97 (16)
Hydrogen-bond geometry (Å, º)
Cg2 represents the centroid of the ring C4a/C5–C8/C8a and Cg3 represents the centroid of the ring C61–C66.
D—H···A
D—H
H···A
D···A
D—H···A
N31—H31A···O11i
N31—H31B···N41
N41—H41···O2ii
N41—H41···O11iii
C6—H6···Cg2iv
0.86
0.86
0.88
0.88
0.95
0.95
2.09
2.55
2.79
2.82
2.88
2.98
2.941 (2)
2.852 (2)
3.503 (2)
3.465 (2)
3.579 (2)
3.719 (2)
169
102
140
131
131
135
C7—H7···Cg3v
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, y+1/2, −z+3/2; (v) −x+1, y−1/2, −z+3/2.
(II) 3-Amino-4-[methyl(phenyl)amino]-1H-isochromen-1-one
Crystal data
C16H14N2O2
Mr = 266.29
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 14.5018 (15) Å
b = 7.7796 (8) Å
c = 11.608 (2) Å
β = 95.728 (13)°
V = 1303.1 (3) Å3
Z = 4
Acta Cryst. (2013). C69, 770-773
sup-4

supplementary materials
F(000) = 560
Dx = 1.357 Mg m−3
µ = 0.09 mm−1
T = 120 K
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 2987 reflections
θ = 3.0–27.5°
Plate, yellow
0.32 × 0.30 × 0.17 mm
Data collection
Bruker Nonius KappaCCD area-detector
diffractometer
Radiation source: Bruker Nonius FR591
rotating anode
Graphite monochromator
Detector resolution: 9.091 pixels mm-1
φ and ω scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.971, Tmax = 0.985
21810 measured reflections
2987 independent reflections
1958 reflections with I > 2σ(I)
Rint = 0.061
θ
max = 27.5°, θmin = 3.0°
h = −18→18
k = −10→10
l = −15→14
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.050
wR(F2) = 0.125
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.07
2987 reflections
182 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0472P)2 + 0.7064P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.22 e Å−3
Δρmin = −0.29 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
C1
0.45967 (12)
0.44055 (8)
0.35632 (12)
0.28499 (12)
0.29941 (12)
0.22963 (12)
0.1698
0.5724 (3)
0.49766 (17)
0.4253 (2)
0.4302 (2)
0.5001 (2)
0.5044 (2)
0.4602
0.71944 (16)
0.61128 (10)
0.57538 (15)
0.64227 (15)
0.75664 (15)
0.83301 (15)
0.8084
0.0265 (4)
0.0252 (3)
0.0232 (4)
0.0224 (4)
0.0223 (4)
0.0242 (4)
0.029*
O2
C3
C4
C4a
C5
H5
C6
0.24700 (13)
0.1990
0.5716 (3)
0.5739
0.94249 (16)
0.9924
0.0273 (4)
0.033*
H6
C7
0.33457 (13)
0.3460
0.6368 (3)
0.6813
0.98137 (17)
1.0577
0.0305 (5)
0.037*
H7
C8
0.40397 (13)
0.4634
0.6362 (3)
0.6812
0.90892 (16)
0.9348
0.0295 (4)
0.035*
H8
C8a
O11
N31
H31A
H31B
N41
C41
C42
0.38688 (12)
0.53605 (9)
0.35618 (11)
0.4020
0.5691 (2)
0.6362 (2)
0.3520 (2)
0.3706
0.79676 (15)
0.73776 (12)
0.47081 (13)
0.4281
0.0234 (4)
0.0381 (4)
0.0314 (4)
0.038*
0.3037
0.3047
0.4423
0.038*
0.19777 (10)
0.16719 (11)
0.07511 (12)
0.3608 (2)
0.2065 (3)
0.1515 (3)
0.59630 (12)
0.64021 (14)
0.61804 (16)
0.0241 (4)
0.0235 (4)
0.0288 (4)
Acta Cryst. (2013). C69, 770-773
sup-5

supplementary materials
H42
C43
0.0310
0.2226
0.5749
0.035*
0.04817 (13)
−0.0144
−0.0068 (3)
−0.0427
−0.1132 (3)
−0.2213
−0.0585 (3)
−0.1295
0.0975 (3)
0.1318
0.65898 (17)
0.6428
0.0336 (5)
0.040*
H43
C44
0.11008 (14)
0.0908
0.72260 (17)
0.7499
0.0330 (5)
0.040*
H44
C45
0.20166 (13)
0.2450
0.74587 (16)
0.7903
0.0293 (4)
0.035*
H45
C46
0.23007 (12)
0.2929
0.70515 (15)
0.7212
0.0254 (4)
0.030*
H46
C47
0.13092 (13)
0.0996
0.4791 (3)
0.4224
0.53655 (17)
0.4681
0.0335 (5)
0.050*
H47A
H47B
H47C
0.1633
0.5817
0.5126
0.050*
0.0850
0.5126
0.5888
0.050*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C1
0.0225 (9)
0.0203 (6)
0.0214 (9)
0.0200 (8)
0.0214 (9)
0.0215 (9)
0.0290 (10)
0.0380 (11)
0.0289 (10)
0.0210 (9)
0.0229 (7)
0.0259 (8)
0.0185 (7)
0.0203 (9)
0.0210 (9)
0.0236 (10)
0.0386 (11)
0.0330 (10)
0.0215 (9)
0.0254 (10)
0.0323 (11)
0.0324 (8)
0.0246 (9)
−0.0012 (8)
−0.0018 (5)
−0.0005 (7)
0.0004 (7)
0.0009 (7)
−0.0010 (7)
0.0000 (8)
−0.0048 (9)
−0.0070 (9)
−0.0013 (7)
−0.0115 (7)
−0.0070 (8)
−0.0008 (6)
0.0003 (8)
0.0001 (8)
−0.0078 (9)
−0.0081 (9)
−0.0018 (9)
−0.0021 (8)
0.0011 (9)
0.0016 (7)
0.0042 (5)
0.0010 (7)
0.0013 (7)
0.0030 (7)
0.0040 (7)
0.0095 (7)
0.0048 (8)
0.0016 (8)
0.0024 (7)
0.0053 (6)
0.0079 (6)
−0.0003 (6)
0.0042 (7)
0.0037 (7)
0.0076 (8)
0.0105 (8)
0.0040 (8)
0.0017 (7)
−0.0045 (8)
−0.0005 (8)
0.0000 (6)
0.0031 (8)
0.0013 (8)
0.0037 (8)
0.0029 (8)
0.0032 (8)
−0.0036 (9)
−0.0008 (9)
0.0021 (8)
−0.0062 (7)
−0.0050 (8)
0.0029 (7)
−0.0036 (8)
−0.0047 (9)
−0.0082 (10)
−0.0032 (9)
−0.0001 (8)
−0.0031 (8)
0.0060 (10)
O2
0.0233 (6)
0.0232 (9)
0.0223 (9)
0.0237 (9)
0.0259 (9)
0.0267 (10)
0.0245 (9)
0.0275 (10)
0.0242 (9)
0.0350 (8)
0.0239 (8)
0.0242 (8)
0.0185 (8)
0.0290 (10)
0.0369 (11)
0.0303 (10)
0.0237 (10)
0.0216 (9)
0.0348 (11)
C3
0.0249 (10)
0.0248 (10)
0.0217 (10)
0.0257 (10)
0.0275 (11)
0.0293 (11)
0.0318 (11)
0.0250 (10)
0.0567 (10)
0.0455 (11)
0.0291 (9)
C4
C4a
C5
C6
C7
C8
C8a
O11
N31
N41
C41
C42
C43
C44
C45
C46
C47
0.0321 (11)
0.0365 (12)
0.0413 (13)
0.0315 (12)
0.0314 (11)
0.0330 (11)
0.0388 (12)
Geometric parameters (Å, º)
C1—O11
C1—O2
C1—C8a
O2—C3
C3—N31
C3—C4
C4—N41
C4—C4a
C4a—C5
C5—C6
1.213 (2)
N31—H31A
0.8799
1.386 (2)
1.452 (3)
1.371 (2)
1.341 (2)
1.354 (2)
1.429 (2)
1.431 (2)
1.411 (2)
1.374 (3)
N31—H31B
N41—C41
N41—C47
C41—C42
C41—C46
C42—C43
C42—H42
C43—C44
C43—H43
0.8800
1.394 (2)
1.461 (2)
1.401 (2)
1.408 (3)
1.390 (3)
0.9500
1.380 (3)
0.9500
Acta Cryst. (2013). C69, 770-773
sup-6

supplementary materials
C5—H5
C6—C7
C6—H6
C7—C8
C7—H7
C8—C8a
C8—H8
C8a—C4a
0.9500
C44—C45
C44—H44
C45—C46
C45—H45
C46—H46
C47—H47A
C47—H47B
C47—H47C
1.395 (3)
0.9500
1.380 (3)
0.9500
0.9500
0.9800
0.9800
0.9800
1.400 (3)
0.9500
1.374 (3)
0.9500
1.402 (3)
0.9500
1.413 (2)
O11—C1—O2
O11—C1—C8a
O2—C1—C8a
C3—O2—C1
N31—C3—C4
N31—C3—O2
C4—C3—O2
C3—C4—N41
C3—C4—C4a
N41—C4—C4a
C5—C4a—C8a
C5—C4a—C4
C8a—C4a—C4
C6—C5—C4a
C6—C5—H5
C4a—C5—H5
C5—C6—C7
C5—C6—H6
C7—C6—H6
C8—C7—C6
C8—C7—H7
C6—C7—H7
C7—C8—C8a
C7—C8—H8
C8a—C8—H8
C8—C8a—C4a
C8—C8a—C1
C4a—C8a—C1
C3—N31—H31A
115.27 (16)
127.31 (17)
117.40 (15)
122.61 (14)
126.76 (17)
111.75 (15)
121.49 (16)
118.27 (16)
119.56 (16)
122.15 (15)
117.42 (16)
123.00 (16)
119.58 (16)
120.89 (17)
119.6
C3—N31—H31B
116.2
H31A—N31—H31B
C41—N41—C4
122.1
119.40 (14)
119.74 (15)
117.40 (16)
121.85 (16)
120.13 (16)
117.97 (18)
120.18 (18)
119.9
C41—N41—C47
C4—N41—C47
N41—C41—C42
N41—C41—C46
C42—C41—C46
C43—C42—C41
C43—C42—H42
C41—C42—H42
C44—C43—C42
C44—C43—H43
C42—C43—H43
C43—C44—C45
C43—C44—H44
C45—C44—H44
C46—C45—C44
C46—C45—H45
C44—C45—H45
C45—C46—C41
C45—C46—H46
C41—C46—H46
N41—C47—H47A
N41—C47—H47B
H47A—C47—H47B
N41—C47—H47C
H47A—C47—H47C
H47B—C47—H47C
119.9
121.63 (18)
119.2
119.2
118.4 (2)
120.8
119.6
120.85 (17)
119.6
120.8
120.87 (19)
119.6
119.6
119.86 (18)
120.1
119.6
120.90 (17)
119.6
120.1
119.81 (17)
120.1
119.6
109.5
120.1
109.5
121.16 (16)
119.70 (16)
119.14 (16)
120.4
109.5
109.5
109.5
109.5
O11—C1—O2—C3
C8a—C1—O2—C3
C1—O2—C3—N31
C1—O2—C3—C4
N31—C3—C4—N41
O2—C3—C4—N41
N31—C3—C4—C4a
O2—C3—C4—C4a
C3—C4—C4a—C5
N41—C4—C4a—C5
−177.68 (17)
1.2 (3)
C4—C4a—C8a—C1
O11—C1—C8a—C8
O2—C1—C8a—C8
O11—C1—C8a—C4a
O2—C1—C8a—C4a
C3—C4—N41—C41
C4a—C4—N41—C41
C3—C4—N41—C47
C4a—C4—N41—C47
C4—N41—C41—C42
1.9 (3)
−4.0 (3)
−176.13 (16)
3.2 (3)
177.23 (17)
175.1 (2)
−3.6 (3)
−4.3 (3)
176.46 (16)
174.21 (18)
−5.0 (3)
108.4 (2)
−70.1 (2)
−92.6 (2)
88.9 (2)
−177.78 (18)
0.7 (3)
165.59 (17)
Acta Cryst. (2013). C69, 770-773
sup-7

supplementary materials
C3—C4—C4a—C8a
N41—C4—C4a—C8a
C8a—C4a—C5—C6
C4—C4a—C5—C6
C4a—C5—C6—C7
C5—C6—C7—C8
C6—C7—C8—C8a
C7—C8—C8a—C4a
C7—C8—C8a—C1
C5—C4a—C8a—C8
C4—C4a—C8a—C8
C5—C4a—C8a—C1
2.4 (3)
C47—N41—C41—C42
7.1 (3)
−179.09 (17)
−0.7 (3)
C4—N41—C41—C46
C47—N41—C41—C46
N41—C41—C42—C43
C46—C41—C42—C43
C41—C42—C43—C44
C42—C43—C44—C45
C43—C44—C45—C46
C44—C45—C46—C41
N41—C41—C46—C45
C42—C41—C46—C45
−16.9 (2)
−175.39 (17)
177.10 (17)
−0.4 (3)
179.47 (18)
−0.3 (3)
1.0 (3)
0.4 (3)
−0.5 (3)
0.2 (3)
−0.6 (3)
−0.8 (3)
178.55 (19)
1.2 (3)
0.8 (3)
−177.74 (16)
−0.1 (3)
−178.99 (17)
−177.96 (17)
Hydrogen-bond geometry (Å, º)
Cg2 represents the centroid of the ring C4a/C5–C8/C8a and Cg3 represents the centroid of the ring C61–C66.
D—H···A
D—H
H···A
D···A
D—H···A
N31—H31A···O2i
N31—H31A···O11i
N31—H31B···N41
C46—H46···O11ii
C6—H6···Cg3iii
0.88
0.88
0.88
0.95
0.95
0.95
2.58
2.20
2.51
2.48
2.62
2.69
3.395 (2)
3.011 (2)
2.841 (2)
3.404 (2)
3.449 (2)
3.571 (2)
154
152
103
164
146
155
C45—H45···Cg2iv
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+3/2; (iii) x, −y+1/2, z+1/2; (iv) x, y−1, z.
Acta Cryst. (2013). C69, 770-773
sup-8

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