Chiral one-dimensional hydrogen-bonded architectures constructed from single-enantiomer phosphoric triamides

Article abstract of DOI:10.1107/S2053229618004734

The two single-enantiomer phosphoric triamides N-(2,6-difluorobenzoyl)-N′,N′′-bis[(S)-(?)-α-methylbenzyl]phosphoric triamide, [2,6-F₂-C₆H₃C(O)NH][(S)-(?)-(C₆H₅)CH(CH₃)NH]₂P(O), denoted L-1, and N-(2,6-difluorobenzoyl)-N′,N′′-bis[(R)-(+)-α-methylbenzyl]phosphoric triamide, [2,6-F₂-C₆H₃C(O)NH][(R)-(+)-(C₆H₅)CH(CH₃)NH]₂P(O), denoted D-1, both C₂₃H₂₄F₂N₃O₂P, have been investigated. In their structures, chiral one-dimensional hydrogen-bonded architectures are formed along [100], mediated by relatively strong N—H…O(P) and N—H…O(C) hydrogen bonds. Both assemblies include the noncentrosymmetric graph-set motifs R₂ ²(10), R₂ ¹(6) and C₂ ²(8), and the compounds crystallize in the chiral space group P1. Due to the data collection of L-1 at 120 K and of D-1 at 95 K, the unit-cell dimensions and volume show a slight difference; the contraction in the volume of D-1 with respect to that in L-1 is about 0.3%. The asymmetric units of both structures consist of two independent phosphoric triamide molecules, with the main difference being seen in one of the torsion angles in the OPNHCH(CH₃)(C₆H₅) part. The Hirshfeld surface maps of these levo and dextro isomers are very similar; however, they are near mirror images of each other. For both structures, the full fingerprint plot of each symmetry-independent molecule shows an almost asymmetric shape as a result of its different environment in the crystal packing. It is notable that NMR spectroscopy could distinguish between compounds L-1 and D-1 that have different relative stereocentres; however, the differences in chemical shifts between them were found to be about 0.02 to 0.001 ppm under calibrated temperature conditions. In each molecule, the two chiral parts are also different in NMR media, in which chemical shifts and P–H and P–C couplings have been studied.

Full text of DOI:10.1107/S2053229618004734

research papers
Chiral one-dimensional hydrogen-bonded
architectures constructed from single-enantiomer
phosphoric triamides
ISSN 2053-2296
a
a
b
b
Mahsa Eghbali Toularoud, Mehrdad Pourayoubi, * Michal Du sˇ ek, V a´ clav Eigner
c
and Krishnan Damodaran
Received 27 November 2017
Accepted 22 March 2018
a
b
Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran, Institute of Physics of the
c
Czech Academy of Sciences, Na Slovance 2, 182 21 Prague 8, Czech Republic, and Department of Chemistry,
University of Pittsburgh, Pittsburgh, PA 15260, USA. *Correspondence e-mail: pourayoubi@um.ac.ir
Edited by B. D. Santarsiero, University of Illinois
at Chicago, USA
The two single-enantiomer phosphoric triamides N-(2,6-difluorobenzoyl)-
0
00
Keywords: phosphoric triamide; dextrorotation;
levorotation; crystal structure; NMR spectro-
scopy; Hirshfeld surface analysis; circular
dichroism.
N ,N -bis[(S)-(ꢀ)-ꢀ-methylbenzyl]phosphoric triamide, [2,6-F -C H C(O)NH]-
2 6 3
[(S)-(ꢀ)-(C H )CH(CH )NH] P(O), denoted L-1, and N-(2,6-difluorobenzoyl)-
6
5
3
2
0
00
N ,N -bis[(R)-(+)-ꢀ-methylbenzyl]phosphoric triamide, [2,6-F -C H C(O)NH]-
2
6
3
[(R)-(+)-(C H )CH(CH )NH] P(O), denoted D-1, both C H F N O P, have
6 5 3 2 23 24 2 3 2
been investigated. In their structures, chiral one-dimensional hydrogen-bonded
architectures are formed along [100], mediated by relatively strong N—
Hꢁ ꢁ ꢁO(P) and N—Hꢁ ꢁ ꢁO(C) hydrogen bonds. Both assemblies include the
CCDC references: 1831741; 1831740
Supporting information: this article has
2
1
2
supporting information at journals.iucr.org/c
noncentrosymmetric graph-set motifs R (10), R (6) and C (8), and the
2 2 2
compounds crystallize in the chiral space group P1. Due to the data collection
of L-1 at 120 K and of D-1 at 95 K, the unit-cell dimensions and volume show a
slight difference; the contraction in the volume of D-1 with respect to that in L-1
is about 0.3%. The asymmetric units of both structures consist of two
independent phosphoric triamide molecules, with the main difference being
seen in one of the torsion angles in the OPNHCH(CH )(C H ) part. The
3
6
5
Hirshfeld surface maps of these levo and dextro isomers are very similar;
however, they are near mirror images of each other. For both structures, the full
fingerprint plot of each symmetry-independent molecule shows an almost
asymmetric shape as a result of its different environment in the crystal packing.
It is notable that NMR spectroscopy could distinguish between compounds L-1
and D-1 that have different relative stereocentres; however, the differences in
chemical shifts between them were found to be about 0.02 to 0.001 ppm under
calibrated temperature conditions. In each molecule, the two chiral parts are
also different in NMR media, in which chemical shifts and P–H and P–C
couplings have been studied.
1
. Introduction
Chiral compounds are of great importance, not only because
of their numerous potential applications in different domains
of chemistry-based sciences or their predominance in biolo-
gical systems, but also due to their attractive structural
features and topologies (Prins et al., 1999). Many research
teams have devoted their efforts to the design and discovery of
various chiral compounds with different functional groups,
and the alteration of structural requirements to achieve
desired properties, most typically in nonlinear optics (Gu et al.,
2016), circularly polarized light-emitting devices (Zinna et al.,
2015), enantioselective catalysts (Headley & Marsden, 2007;
Hua et al., 1987) or medicine (De Luca et al., 2017).
Phosphoric triamides have found widespread use in organic
synthesis (Li et al., 2012), coordination chemistry (Saneei et al.,
2016) and biochemistry (Manunza et al., 1999). Chiral
#
2018 International Union of Crystallography
Acta Cryst. (2018). C74
https://doi.org/10.1107/S2053229618004734 1 of 10

research papers
Table 1
Experimental details.
L-1
D-1
Crystal data
Chemical formula
C
443.4
Triclinic, P1
120
9.7608 (3), 10.6134 (3), 11.2721 (3)
77.398 (2), 75.589 (2), 87.635 (2)
1103.64 (6)
2
Cu Kꢀ
1.47
0.53 ꢄ 0.19 ꢄ 0.08
23
H
24
F
2
N
3
O
2
P
23 24 2 3 2
C H F N O P
443.4
Triclinic, P1
95
9.7524 (2), 10.6117 (2), 11.2510 (2)
77.3381 (15), 75.6221 (16), 87.7313 (16)
1100.33 (4)
M
r
Crystal system, space group
Temperature (K)
˚
a, b, c (A)
ꢃ
ꢀ
, ꢁ, ꢂ ( )
˚
3
V (A )
Z
Radiation type
2
Cu Kꢀ
1.46
0.29 ꢄ 0.09 ꢄ 0.07
ꢀ
1
ꢃ (mm
Crystal size (mm)
)
Data collection
Diffractometer
Agilent Xcalibur/Gemini ultra diffractometer
with an AtlasS2 detector
Agilent SuperNova Dual Source diffractometer
with an AtlasS2 detector
Absorption correction
Analytical (CrysAlis PRO; Rigaku OD, 2015)
0.562, 0.896
21163, 7492, 6976
Analytical (CrysAlis PRO; Rigaku OD, 2015)
0.774, 0.917
16006, 7660, 7383
Tmin, Tmax
No. of measured, independent and observed
I > 3ꢄ(I)] reflections
[
R
int
0.051
0.598
0.034
0.607
˚
ꢀ1
)
(sin ꢅ/ꢆ)max (A
Refinement
2
2
2
R[F > 3ꢄ(F )], wR(F ), S
No. of reflections
0.047, 0.121, 1.71
7492
0.039, 0.098, 1.50
7660
No. of parameters
No. of restraints
H-atom treatment
578
6
578
6
H atoms treated by a mixture of independent
and constrained refinement
0.30, ꢀ0.31
H atoms treated by a mixture of independent
and constrained refinement
0.17, ꢀ0.22
˚
ꢀ3
)
ꢀꢇ
max, ꢀꢇmin (e A
Absolute structure 3604 Friedel pairs used in the refinement
Absolute structure parameter ꢀ0.014 (14)
Computer programs: CrysAlis PRO (Rigaku OD, 2015), CrystalExplorer (Wolff et al., 2013), JANA2006 (Version 24/09/2015; Pet rˇ ı´ cˇ ek et al., 2014), SUPERFLIP (Palatinus & Chapuis,
3546 Friedel pairs used in the refinement
0.014 (17)
2
007) and MCE2005 (Rohl ı´ cek & Hus a´ k, 2007).
phosphoric triamides have been used as strong Lewis bases in
asymmetric catalysis processes (Denmark & Stavenger, 2000;
Buono et al., 1999), as herbicides, plant-growth regulators
(Diel & Maier, 1984) and insecticides (Reid & Marmor, 1978),
and as moieties of nucleotides (Hah et al., 1999).
efforts included the study of both the molecular and crystal
structure geometry (Pourayoubi et al., 2012), and the patterns
of intermolecular interactions (Pourayoubi et al., 2014).
The crystal structures of chiral phosphoric triamides are
absent in the CSD; therefore, we were interested in the
synthesis and X-ray crystal structure analysis of chiral phos-
phoric triamide molecules in order to study the influence of
chirality on the hydrogen-bond pattern. In a previous article,
we reported the X-ray crystal structure of the first chiral
1
2
[
RC(O)NH](R R N) P(O) phosphoric triamide, namely [CCl -
2 3
C(O)NH][R-(+)(C H )CH(CH )NH] P(O)ꢁ0.25H O (Ariani
6
5
3
2
2
et al., 2017); however, an attempt to analyse its enantiomer by
X-ray diffraction was unsuccessful.
It is noteworthy that single-enantiomer compounds with
potential applications as ligands in coordination chemistry,
such as phosphoric triamides, could be useful, since it would
then be possible to design different metal-containing mol-
ecular assemblies. We report here the first pair of single-
enantiomer phosphoric triamide structures, as levo- and
dextrorotatory isomers, namely [2,6-F -C H C(O)NH]-
In a series of recently published papers, crystal-engineering
approaches have been used for the generating of ‘empirical
rules’ for predicting the pattern of hydrogen bonding based on
molecular structures (Pourayoubi et al., 2014; Sabbaghi et al.,
2
6
3
[(S)-(ꢀ)(C H )CH(CH )NH] P(O), denoted L-1, and [2,6-F -
6
5
3
2
2
C H C(O)NH][R-(+)(C H )CH(CH )NH] P(O), denoted D-1
6
3
6
5
3
2
2017). The structures of several new derivatives, determined
by X-ray diffraction and archived in the Cambridge Structural
Database (CSD; Groom et al., 2016), were examined. These
(see Scheme). The study is complemented by an investigation
of the intermolecular interactions, incorporating a Hirshfeld
surface-based analysis (Spackman & Jayatilaka, 2009). The
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results of IR, MS, NMR and UV spectroscopic analyses, and
circular dichroism (CD) are discussed.
solution of [2,6-F -C H C(O)NH]Cl P(O) (2.1 mmol) in the
2
6
3
2
same solvent (20 ml). After stirring at 273 K for 4 h, the
solvent was evaporated in a vacuum and the solid obtained
was washed with distilled water. Single crystals of L-1, suitable
for X-ray crystallography, were obtained from a solution of the
2
. Experimental
.1. Synthesis and crystallization
.1.1. Preparation of [2,6-F -C H C(O)NH]Cl P(O). The
2
product in a mixture of CH OH and CHCl (1:1 v/v) by slow
3 3
evaporation at room temperature (yield > 60%).
ꢀ1
2
2
6
3
2
Analytical data: m.p. 504 K. IR (KBr, ꢈ, cm ): 3247, 3081,
029, 1745, 1671, 1626, 1588, 1471, 1423, 1287, 1238, 1199, 1116,
1
phosphorus–chlorine reagent [2,6-F -C H C(O)NH]Cl P(O)
2
6
3
2
3
was synthesized according to a literature method (Tarahhomi
et al., 2013) from the reaction between phosphorus penta-
chloride (9.5 mmol) and 2,6-F -C H C(O)NH (9.5 mmol) in
1
079, 1044, 1011, 974, 892, 857, 820, 787, 744, 698. H NMR
(
601 MHz, DMSO-d ): ꢉ 9.80 (s, 1H), 7.50 (tt, J = 8.5, 6.6 Hz,
6
2
6
3
2
1
4
1
6
H), 7.39–7.31 (m, 4H), 7.31–7.24 (m, 4H), 7.22–7.11 (m, 4H),
.97 (t, J = 10.5 Hz, 1H), 4.88 (t, J = 10.0 Hz, 1H), 4.45–4.37 (m,
H), 4.37–4.29 (m, 1H), 1.40 (d, J = 6.9 Hz, 3H), 1.38 (d, J =
dry CCl (20 ml) at 348 K (about 3 h), followed by treatment
4
with formic acid (85%, 9.5 mmol) at ice-bath temperature.
2.1.2. Preparation of L-1. For the preparation of L-1, a
13
.8 Hz, 3H); C NMR (151 MHz, DMSO-d ): ꢉ 161.65, 158.77
6
solution of (S)-(ꢀ)-ꢀ-methylbenzylamine (4.2 mmol) and tri-
(
dd, J = 249.1, 7.8 Hz), 146.24 (d, J = 5.5 Hz), 145.89 (d, J =
ethylamine (4.2 mmol) in CHCl (10 ml) was added to a
3
5
1
2
4
.6 Hz), 131.84 (t, J = 19.2 Hz), 127.98, 127.97, 126.34, 126.31,
26.06, 125.96, 115.35 (td, J = 22.5, 8.4 Hz), 111.84 (d, J =
3.7 Hz), 50.03, 49.68, 25.48 (d, J = 5.3 Hz), 24.92 (d, J =
31
1
19
.9 Hz); P{ H} NMR (243 MHz, DMSO-d ): ꢉ 3.75; F NMR
6
(
565 MHz, DMSO-d ): ꢉ ꢀ113.50 (t, J = 7.2 Hz). MS (70 eV,
6
+
+
EI): 443 (6) [M] , 338 (20) [M ꢀ C H ] , 323 (5) [M ꢀ
8
9
+
+
+
C H NH] , 302 (3) [M ꢀ C H F O] , 167 (6) [C H NOP] ,
8
9
7
3
2
8
10
+
+
56 (10) [C H F NO] , 141 (38) [C H F O] , 120 (100)
1
7 4 2 7 3 2
+
+
+
[
C H N] , 105 (55) [C H ] , 77 (17) [C H ] . UV (CHCl ):
8 10 8 9 6 5 3
25
ꢆmax = 258 nm. [ꢀ] = ꢀ43.0 (c 0.004, MeOH). CD band:
D
ꢀ
"max = ꢀ21 (272 nm).
2.1.3. Preparation of D-1. Compound D-1 was synthesized
by a similar method to that used for the preparation of L-1,
but using (R)-(+)-ꢀ-methylbenzylamine instead of (S)-(ꢀ)-ꢀ-
methylbenzylamine (yield > 60%).
ꢀ
1
Analytical data: m.p. 504 K. IR (KBr, ꢈ, cm ): 3248, 3082,
029, 2970, 2919, 1744, 1672, 1626, 1591, 1470, 1432, 1286, 1235,
199, 1116, 1079, 1044, 1011, 975, 892, 860, 820, 786, 748, 697.
3
1
+
+
MS (70 eV, EI): 443 (6) [M] , 338 (21) [M ꢀ C H ] , 323 (5)
8
9
+
+
+
[
M ꢀ C H NH] , 167 (7) [C H NOP] , 141 (39) [C H F O] ,
8
9
8
10
7
3 2
+
20 (100) [C H N] , 105 (56) [C H ] , 77 (16) [C H ] . UV
+
+
1
8
10
8
9
6
5
25
(
CHCl ): ꢆ
= 259 nm. [ꢀ] = 44.5 (c 0.004, MeOH). CD
max D
3
band: ꢀ"max = +20 (270 nm). Details of the NMR experiments
are given in the supporting information.
2.2. Refinement
Crystal data, data collection and structure refinement
details are summarized in Table 1. For L-1 and D-1, all H
atoms were discernible in difference Fourier maps and could
be refined with reasonable geometries. According to common
practice, H atoms bonded to C atoms were kept in ideal
˚
positions, with C—H = 0.96 A, while the positions of H atoms
on N atoms were refined freely. In both cases, U (H) values
iso
were set at 1.2U (C,N). All non-H atoms were refined using
eq
harmonic refinement.
3
. Results and discussion
Figure 1
Displacement ellipsoid plots (50% probability) of the components of the
asymmetric units of L-1 and D-1, showing the atom-numbering schemes
for non-H and non-C atoms. H atoms are drawn as spheres of arbitrary
radii.
3.1. Description of the crystal structures
Both L-1 and D-1 crystallize in the chiral space group P1.
The observed chirality can be understood in terms of chirality
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Eghbali Toularoud et al.
Two single-enantiomer phosphoric triamides 3 of 10

research papers
transfer from the chiral phosphoric triamide molecule to the
whole crystal packing. In the two structures, the unit-cell
dimensions and volumes are slightly different, due to the fact
that data collection was at different temperatures, i.e. 120 K
for L-1 and 95 K for D-1. We observed a contraction of about
0.3% in the volume of the unit cell measured at the lower
temperature, as well as a contraction of the unit-cell dimen-
sions a, b and c, with the most significant contraction (of about
Table 2
Selected geometric parameters (A, ) for L-1.
˚
ꢃ
Molecule L-1a
Molecule L-1b
P1—O1
P1—N1
P1—N2
P1—N3
N1—C1
N2—C8
N3—C16
1.481 (2)
1.703 (2)
1.621 (2)
1.624 (2)
1.351 (4)
1.461 (3)
1.459 (4)
1.477 (2)
1.699 (3)
1.619 (3)
1.620 (2)
1.358 (4)
1.447 (3)
1.458 (4)
0
.19%) being in the c direction, (cD-1 – cL-1)/cL-1 ꢄ 100, where
the weaker intermolecular contacts were observed. The Flack
O1—P1—N1
O1—P1—N2
O1—P1—N3
N1—P1—N2
N1—P1—N3
N2—P1—N3
P1—N1—C1
P1—N2—C8
P1—N3—C16
103.50 (12)
115.22 (11)
115.23 (13)
109.74 (13)
109.45 (11)
103.69 (12)
124.0 (2)
103.20 (12)
116.02 (11)
116.30 (13)
109.56 (14)
109.49 (12)
102.25 (12)
126.2 (2)
(
1983) parameters of 0.014 (17) and ꢀ0.014 (14) for L-1 and
D-1, respectively, show that the absolute configurations, as
assigned, are correct.
The asymmetric units of both structures consist of two
symmetry-independent phosphoric triamide molecules (de-
noted with suffixes a and b hereafter). Fig. 1 shows the
components of the asymmetric units of the two structures, with
the atom-numbering schemes for the non-H and non-C atoms.
The arrangement of the two molecules in the structure of L-1
shows a near mirror-image relationship with respect to the
molecules in the structure of D-1. The a and b molecules in
each structure adopt similar conformations, which is apparent
from the small differences in the torsion angles (see Tables 2
and 3). The most pronounced differences were observed in the
pairs of torsion angles O1—P1—N3—C16, P1—N2—C8—C9
and P1—N2—C8—C10. On the other hand, the L-1a and D-1a
molecules are very similar with regard to their bond lengths,
angles and torsion angles; however, the torsion angles appear
with opposite signs. For example, the P1a—N2a—C8a—C9a
123.39 (19)
123.52 (19)
125.02 (19)
123.6 (2)
P1—N2—C8—C9
P1—N3—C16—C17
O1—P1—N1—C1
O1—P1—N2—C8
O1—P1—N3—C16
P1—N1—C1—O2
P1—N2—C8—C10
P1—N3—C16—C18
88.4 (3)
117.7 (2)
100.4 (3)
121.6 (3)
ꢀ178.4 (2)
55.9 (3)
ꢀ176.68 (19)
51.6 (3)
ꢀ25.2 (3)
ꢀ2.2 (3)
ꢀ41.6 (3)
1.0 (3)
ꢀ134.6 (2)
ꢀ115.4 (2)
ꢀ147.5 (2)
ꢀ117.2 (2)
the spacefilling representation of two symmetry-independent
molecules in the two structures is given, which shows that
molecules specified with the same colours in two crystals are in
a near mirror-image relationship with respect to each other
(Fig. 3).
ꢃ
torsion angles in L-1a and D-1a are 88.4 (3) and ꢀ88.5 (2) ,
respectively. In order to present the full-numbering scheme,
molecule D-1a is shown as an example (Fig. 2). Furthermore,
Selected geometric parameters and hydrogen-bond geom-
etries for L-1 and D-1 are given in Tables 2–5. The P O, P—N
Table 3
Selected geometric parameters (A, ) for D-1.
˚
ꢃ
Molecule D-1a
Molecule D-1b
P1—O1
P1—N1
P1—N2
P1—N3
N1—C1
N2—C8
N3—C16
1.4808 (17)
1.7081 (18)
1.6219 (19)
1.6199 (17)
1.355 (3)
1.4784 (17)
1.6986 (19)
1.618 (2)
1.6181 (17)
1.367 (3)
1.459 (3)
1.469 (2)
1.463 (3)
1.460 (3)
O1—P1—N1
O1—P1—N2
O1—P1—N3
N1—P1—N2
N1—P1—N3
N2—P1—N3
P1—N1—C1
P1—N2—C8
P1—N3—C16
103.29 (9)
115.49 (8)
115.08 (10)
109.87 (10)
109.77 (8)
103.37 (9)
123.03 (15)
122.96 (14)
123.75 (16)
102.89 (9)
116.28 (8)
116.30 (10)
109.74 (10)
109.71 (9)
101.94 (10)
125.57 (16)
124.36 (15)
123.82 (16)
P1—N2—C8—C9
P1—N3—C16—C17
O1—P1—N1—C1
O1—P1—N2—C8
O1—P1—N3—C16
P1—N1—C1—O2
P1—N2—C8—C10
P1—N3—C16—C18
ꢀ88.5 (2)
ꢀ117.68 (19)
177.16 (16)
ꢀ51.78 (19)
25.1 (2)
1.4 (3)
147.93 (15)
116.90 (18)
ꢀ101.0 (2)
ꢀ121.47 (19)
178.46 (17)
ꢀ55.44 (19)
42.1 (2)
Figure 2
ꢀ1.2 (3)
Displacement ellipsoid plot (50% probability) for one of the independent
molecules (molecule a) of D-1, showing the atom-numbering scheme. H
atoms are drawn as spheres of arbitrary radii.
134.66 (16)
115.40 (19)
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Table 4
Hydrogen-bond geometry (A, ) for L-1.
˚
ꢃ
D—Hꢁ ꢁ ꢁA
D—H
Hꢁ ꢁ ꢁA
Dꢁ ꢁ ꢁA
D—Hꢁ ꢁ ꢁA
N1a—H1n1aꢁ ꢁ ꢁO2b
N2a—H1n2aꢁ ꢁ ꢁO1b
N3a—H1n3aꢁ ꢁ ꢁO1b
0.86 (2)
0.860 (9)
0.86 (2)
0.860 (17)
0.860 (14)
0.86 (2)
0.96
2.019 (18)
2.111 (11)
2.12 (3)
1.967 (15)
2.036 (13)
2.06 (3)
2.874 (3)
2.919 (3)
2.942 (3)
2.822 (3)
2.868 (3)
2.888 (3)
3.278 (4)
172 (3)
156 (3)
160 (3)
173 (3)
163 (3)
163 (3)
162.01
i
i
ii
N1b—H1n1bꢁ ꢁ ꢁO2a
N2b—H1n2bꢁ ꢁ ꢁO1a
N3b—H1n3bꢁ ꢁ ꢁO1a
iii
C5a—H1c5aꢁ ꢁ ꢁO1a
2.35
Symmetry codes: (i) x ꢀ 1; y; z; (ii) x þ 1; y; z; (iii) x; y ꢀ 1; z.
Table 5
Hydrogen-bond geometry (A, ) for D-1.
˚
ꢃ
D—Hꢁ ꢁ ꢁA
D—H
Hꢁ ꢁ ꢁA
Dꢁ ꢁ ꢁA
D—Hꢁ ꢁ ꢁA
i
C5a—H1c5aꢁ ꢁ ꢁO1a
0.96
2.34
3.271 (3)
2.863 (2)
2.907 (2)
2.938 (3)
2.812 (2)
2.858 (2)
2.887 (3)
162.23
173 (3)
154 (3)
155 (2)
173 (2)
158 (3)
157 (2)
N1a—H1n1aꢁ ꢁ ꢁO2b
N2a—H1n2aꢁ ꢁ ꢁO1b
N3a—H1n3aꢁ ꢁ ꢁO1b
0.862 (18)
0.859 (12)
0.861 (19)
0.865 (16)
0.856 (10)
0.861 (17)
2.006 (16)
2.110 (12)
2.13 (2)
1.951 (14)
2.046 (13)
2.07 (2)
ii
ii
iii
N1b—H1n1bꢁ ꢁ ꢁO2a
N2b—H1n2bꢁ ꢁ ꢁO1a
N3b—H1n3bꢁ ꢁ ꢁO1a
Figure 3
A spacefilling representation of the two symmetry-independent mol-
ecules in the structures of L-1 and D-1.
Symmetry codes: (i) x; y þ 1; z; (ii) x þ 1; y; z; (iii) x ꢀ 1; y; z.
ꢃ
115.23 (13) (O1a—P1a—N3a) for L-1a, from 102.25 (12)
(N2b—P1b—N3b) to 116.30 (13) (O1b—P1b—N3b) for
ꢃ
and C O bond lengths are all within the ranges observed in
analogous structures (Keikha et al., 2016; Vahdani Alviri et al.,
ꢃ
L-1b, from 103.29 (9) (O1a—P1a—N1a) to 115.49 (8) (O1a—
P1a—N2a) for D-1a and from 101.94 (10) (N2b—P1b—N3b)
2018). The P—N bond of the C(O)NHP(O) segment is longer
ꢃ
than the other two P—N bonds. This is related to the inter-
action of the corresponding N atom with the C O ꢊ system,
which leads to a smaller C—N bond length in the
C(O)NHP(O) segment with respect to the other two C—N
bonds in each molecule. The P—N—C angles in isomers L-1
to 116.30 (10) (O1b—P1b—N3b) for D-1b. This means that
in all four molecules, the largest angle is O1—P1—N2/N3,
while the smallest angle in the a molecules is O1—P1—N1 and
in the b molecules is N2—P1—N3.
In each molecule, the mean plane defined by atoms C1/O2/
N1 is not coplanar with the mean plane defined by the atoms
ꢃ
and D-1 [123.39 (19)–126.2 (2) and 122.96 (14)–125.57 (16) ,
2
respectively] show less p character with respect to sp hybri-
of the 2,6-F
-C
H
segment (see Table 6) and, typically, as in
2
6
3
ꢃ
dization; however, the sums of the surrounding angles at the N
atoms (C—N—P + P—N—H + H—N—C) are near or equal to
L-1b, the angle between the mean planes is 53.4 (3) .
The O atom of the C O group in the b molecules in both
structures shows a close contact with an adjacent F atom in the
2
the bond-angle sum for ideal sp hybridization (360 ).
ꢃ
˚
In both structures, the P atoms are within a distorted
tetrahedral (N)(N) P(O) environment, with the angles at the
P atom ranging from 103.50 (12) (O1a—P1a—N1a) to
other independent molecule [Oꢁ ꢁ ꢁF = 2.976 (3) A in L-1 and
˚
2.964 (2) A in D-1]. In the C(O)NHP(O) segment, the inter-
planar angle between the mean planes defined by atoms C1/
2
Figure 4
Aview of the one-dimensional array of L-1 and D-1 built from N—Hꢁ ꢁ ꢁO(P) and N—Hꢁ ꢁ ꢁO(C) hydrogen bonds (dotted lines). H atoms not involved in
hydrogen bonding have been omitted for clarity. Molecules with the same coloured C atoms are related by symmetry.
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Table 6
Interplanar angles ( ) for L-1 and D-1.
dimensional maps, as well as two-dimensional fingerprint plots
(Spackman & Jayatilaka, 2009), is very useful.
The HS mapped with dnorm (Spackman & McKinnon, 2002)
ꢃ
Structure Atoms defining plane 1 Atoms defining plane 2
Angle
and two-dimensional fingerprint plots were generated using
CrystalExplorer (Wolff et al., 2013). Each point on the HS is
associated with the nearest distance from the point to nuclei
inside (d ) and outside (d ) the surface. Moreover, the
L-1
L-1
D-1
D-1
C1a, O2a, N1a
C1b, O2b, N1b
C1a, O2a, N1a
C1b, O2b, N1b
C2a, C3a, C4a, C5a, C6a,
C7a, F1a, F2a, H1c4a,
H1c5a, H1c6a
C2b, C3b, C4b, C5b, C6b, 53.4 (3)
C7b, F1b, F2b, H1c4b,
H1c5b, H1c6b
C2a, C3a, C4a, C5a, C6a,
C7a, F1a, F2a, H1c4a,
H1c5a, H1c6a
C2b, C3b, C4b, C5b, C6b, 53.3 (2)
C7b, F1b, F2b,
H1c4b, H1c5b, H1c6b
51.3 (3)
i
e
normalized contact distance (dnorm), based on the d , d and
i
e
51.1 (2)
the van der Waals (vdW) radii of the corresponding atoms,
assigns a particular intermolecular interaction via a colour-
coded system. In the HS mapped with dnorm, red and blue
colours are associated with distances shorter and longer than
the vdW radii of neighbouring atoms, respectively, while white
is used for contacts near the vdW separations (McKinnon et
al., 2007).
L-1
L-1
D-1
D-1
C1a, O2a, N1a, H1n1a
C1b, O2b, N1b, H1n1b
C1a, O2a, N1a, H1n1a
C1b, O2b, N1b, H1n1b
P1a, O1a, N1a, H1n1a
P1b, O1b, N1b, H1n1b
P1a, O1a, N1a, H1n1a
P1b, O1b, N1b, H1n1b
2.7 (12)
1.5 (13)
2.2 (12)
1.5 (13)
For L-1 and D-1, the HSs are plotted separately for the two
symmetry-independent phosphoric triamide molecules (Fig. 6).
In these structures, the intermolecular contacts are similar,
with the most important interactions being four N—Hꢁ ꢁ ꢁO(P)
O2/N1/H1n1 and P1/O1/N1/H1n1 shows an anti conformation
of the C1—O2 and P1—O1 groups (see Table 6). As the syn
and anti notations are usually applied to the conformation on
a single bond, we derive the torsion angle O1—P1ꢁ ꢁ ꢁC1—O2,
(labels 1, 2, 4 and 5) and two N—Hꢁ ꢁ ꢁO(C) (labels 3 and 6)
hydrogen bonds, appearing as large red areas in the corre-
sponding HS maps. In both structures, the C—Hꢁ ꢁ ꢁOP
hydrogen bond between two adjacent symmetry-related a
molecules is visible as a moderate red area in the HS (Fig. 6a
for L-1 and Fig. 6b for D-1, label 7). Moreover, pale-red spots
in Figs. 6(c) and 6(d) correspond to C—Hꢁ ꢁ ꢁC (label 8), C—
Hꢁ ꢁ ꢁOP (label 9) and C—Hꢁ ꢁ ꢁH—C (label 10) contacts
between two adjacent symmetry-related b molecules in both
structures.
ꢃ
with a hypothetical bond between P1ꢁ ꢁ ꢁC1, as ꢀ177.2 (2) in
D-1b. The N—H unit of the C(O)NHP(O) part adopts a syn
conformation with respect to the P O group, while the two
other N—H units adopt an anti conformation with respect to
the P O group.
In both crystal structures, the two symmetry-independent
molecules are linked through N—Hꢁ ꢁ ꢁO hydrogen bonds in a
tape arrangement along the a axis. This arrangement is shown
in Fig. 4(a) for L-1, and a similar assembly, but nearly in a
mirror-image position with respect to this arrangement, is seen
for D-1, as shown in Fig. 4(b). These patterns include
noncentrosymmetric hydrogen-bonded graph-set motifs
The fingerprint plots (FPs) of the close contacts are very
similar for the molecules with the same suffix in each structure,
2
2
1
2
R (10) and R (6) (for graph-set notation, see Etter et al.,
1990), with the O atom of phosphoryl group taking part in a
three-centred (N Hꢁ ꢁ ꢁ)(N Hꢁ ꢁ ꢁ)O grouping, while the O
P
P
atom of the carbonyl group co-operates in an N Hꢁ ꢁ ꢁO
CP
hydrogen bond [N is the N atom of the C(O)NHP(O)
CP
segment and N are the other two N atoms]. In this assembly,
P
molecules a and b are arranged in the sequence ababab . . . in
2
both structures, leading to a chain C (8) motif. It should be
2
noted that the phosphoric triamide molecules include two
dissymmetry centres, and in the crystal with two symmetry-
independent molecules, we can consider four such dissym-
metry centres, which are responsible for the chiral architecture
formed. For both structures, the one-dimensional tape
arrangement is extended through C—Hꢁ ꢁ ꢁO hydrogen bonds
into a two-dimensional architecture which includes a high-
5
6
order hydrogen-bonded cyclic R (28) motif. An example of
this type of assembly is shown for compound L-1 in Fig. 5.
3.2. Hirshfeld surface analysis and fingerprint plots
Figure 5
For a better understanding of the packing map, it was
Part of the crystal packing of compound L-1, showing the two-
dimensional arrangement along the ab plane, mediated by N—Hꢁ ꢁ ꢁO
and C—Hꢁ ꢁ ꢁO hydrogen bonds. H atoms not involved in hydrogen
bonding have been omitted for clarity.
decided to use a graphical tool for identification of the inter-
molecular interactions within the crystal structure. In this
respect, the Hirshfeld surface (HS) analysis, which uses three-
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and examples of the plots for molecule L-1a are given in Fig. 7;
the contribution of each type of contact, relative to the
corresponding structure, is given in Table S1 of the supporting
information. In each structure, the FPs of the independent
molecules are not identical because there are different mol-
ecular environments of the symmetry-independent molecules,
as well as slightly different molecular conformations, as has
been shown for structures with more than one component in
the crystal (Fabbiani et al., 2007). In both structures, the
Hꢁ ꢁ ꢁH, Cꢁ ꢁ ꢁH/Hꢁ ꢁ ꢁC, Oꢁ ꢁ ꢁH/Hꢁ ꢁ ꢁO and Fꢁ ꢁ ꢁH/Hꢁ ꢁ ꢁF
contacts have considerable contributions, while the Cꢁ ꢁ ꢁC,
Nꢁ ꢁ ꢁH/Hꢁ ꢁ ꢁN, Oꢁ ꢁ ꢁC/Cꢁ ꢁ ꢁO, Fꢁ ꢁ ꢁC/Cꢁ ꢁ ꢁF and Fꢁ ꢁ ꢁO/Oꢁ ꢁ ꢁF
contacts contribute negligibly. The Hꢁ ꢁ ꢁH contacts represent
the largest relative interaction in the four molecules of the two
structures, typically amounting to 51.8% for L-1a and 53.9%
for L-1b, with one distinct spike for the shortest distance of de
˚
= d ’ 1.2 A. For molecule L-1a, the proportions of the Cꢁ ꢁ ꢁH/
i
Hꢁ ꢁ ꢁC, Fꢁ ꢁ ꢁH/Hꢁ ꢁ ꢁF and Oꢁ ꢁ ꢁH/Hꢁ ꢁ ꢁO contacts with respect
to the total surface are 21.8, 11.3 and 9.2%, respectively, and
similar contacts in molecule L-1b show 20.5, 11.5 and 9.2%
proportions. In the FPs, the Cꢁ ꢁ ꢁH/Hꢁ ꢁ ꢁC contacts appear as
two short spikes, while the Oꢁ ꢁ ꢁH/Hꢁ ꢁ ꢁO interactions reveal
two sharp spikes. It should be noted that the shortest d + d in
i
e
˚
spikes of Oꢁ ꢁ ꢁH/Hꢁ ꢁ ꢁO interactions is near 1.8 A. Indeed,
Figure 6
Front and back views of the Hirshfeld surfaces for molecules L-1a, D-1a, L-1b and D-1b. For guidance, the ‘ball-and-stick’ representations of the
phosphoric triamide molecules are shown on the left, with the orientations according to the middle figure. The interactions are numbered and defined
here. For molecules L-1a, D-1a, L-1b and D-1b: N3a—H1n3aꢁ ꢁ ꢁO1b—P1b (1), N2a—H1n2aꢁ ꢁ ꢁO1b—P1b (2), C1a—O2aꢁ ꢁ ꢁH1n1b—N1b (3), P1a—
O1aꢁ ꢁ ꢁH1n2b—N2b (4), P1a—O1aꢁ ꢁ ꢁH1n3b—N3b (5) and N1a—H1n1aꢁ ꢁ ꢁO2b—C1b (6); for molecules L-1a and D-1a only: P1a—O1aꢁ ꢁ ꢁH1c5a—C5a
(7); for molecules L-1b and D-1b only: C6b—H1c6bꢁ ꢁ ꢁC15b (8), C5b—H1c5bꢁ ꢁ ꢁO1b—P1b (9) and C9b—H1c9bꢁ ꢁ ꢁH1c19b—C19b (10).
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is nh tae r rpa c st pi oi kn es .s in this region arise from the strong N—Hꢁ ꢁ ꢁO
0.001 ppm, we need to show that the reproducibility is at least
ten times better than that. So, we ran each of the samples three
times with excellent reproducibility. The details of the
experiments are given in Table S2 of the supporting infor-
mation. Under the equilibrated conditions, the main differ-
ences between the signals of L-1 and D-1 are related to the
3.3. Spectroscopy
In the IR spectra, the N—H stretching frequencies occur at
ꢀ ꢀ1
1
3
247 and 3081 cm for L-1, and at 3248 and 3082 cm for
D-1. In both structures, the lower N—H stretching frequencies
are assigned to the N—H unit of the C(O)NHP(O) segment,
which is involved in a stronger hydrogen bond, as shown by
the X-ray crystallographic analysis.
The NMR spectra of L-1 and D-1 are identical, except for
very small shifts of values for similar signals. As temperature is
important for absolute chemical shifts, the experiments for
both samples were run under calibrated and equilibrated
temperature conditions (303 K). Since the difference in
chemical shifts between L-1 and D-1 are only about 0.02 to
appearance of signals assigned to the N H protons, where a
CP
broad signal centred at 9.76 ppm for L-1 and a doublet signal
(J = 6.0 Hz) at 9.77 ppm for D-1 are seen (see Fig. S1 in the
supporting information); however, the widths at half-maxima
for both these signals are almost the same, i.e. 18.0 Hz for L-1
and 18.2 Hz for D-1.
31
19
It is quite interesting to see that even P and F show a
difference in the chemical shifts between the two samples, and
it is notable that NMR could distinguish compounds that have
3
1
different relative stereocentres. For L-1 and D-1, the
P
Figure 7
Schematic illustration of the fingerprint plots of molecule L-1a. Different colours have been used for different atom pair contacts.
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signals appear at 3.78 and 3.80 ppm, respectively. The values
19
given are the averages of different runs. The F chemical
shifts are at ꢀ113.49 and ꢀ113.48 ppm, respectively. As the
1 13
spectra are very similar, the details of the H and C NMR
analyses are only discussed for one of the samples.
1
In the H NMR spectrum of L-1, besides the N H proton
CP
already discussed above, the two other N—H protons appear
as two triplets at 4.97 (J = 10.5 Hz) and 4.88 ppm (J = 10.0 Hz),
because of the coupling on one hand with the C—H unit and
on the other hand with phosphorus. The ten protons of the
phenyl rings appear as three separate multiplet signals at 7.31–
7.39, 7.24–7.31 and 7.11–7.22 ppm, which belong to the H
atoms bonded to C11/C15/C19/C23, C12/C14/C20/C22 and
C13/C21, respectively, with the integration areas confirming
four protons for the first two signals and two protons for the
third signal (the numbering used is according to the X-ray
crystal structure). Moreover, the protons bonded to C4 and C6
Figure 8
3
CD spectra of L-1 and D-1 in CHCl solution.
ꢀ
1
length (dm), c is concentration (g ml ), and levorotation and
dextrorotation are designated by (ꢀ) and (+), respectively.
2
D
5
(
for the 2,6-F -C H ring) are mixed with the peaks at 7.11–
2
The specific rotations are measured as [ꢀ] = ꢀ43.0 (c 0.004,
6
3
2
D
5
7.22 ppm. The ‘tt’ signal at 7.50 ppm corresponds to the para-H
atom of the 2,6-F -C H segment (the proton bonded to atom
MeOH) for L-1 and [ꢀ] = 44.5 (c 0.004, MeOH) for D-1.
To examine the chiroptical properties of both enantiopure
compounds in solution, the circular dichroism (CD) spectra
were investigated for a 2.3 mM solution in chloroform (Fig. 8).
The CD spectra exhibit opposing signals, with the maximum
intensity of the negative peak at 272 nm for L-1 and a similar
positive peak at 270 nm for D-1. The strong Cotton effect up
to 272/270 nm is according to the spectral region characteristic
of the n!ꢊ* transition bands of the phosphoric triamide
molecule. For L-1, the CD sign is negative at wavelengths
below 208 nm, while it is positive between 208 and 251 nm. For
D-1, opposite signs are observed below 211 nm and from 211
to 246 nm. The CD patterns of L-1 and D-1 are nearly mirror
images in the range 200–400 nm.
2
6
3
C5). A comparison of this signal at 400 and 600 MHz is given
in Fig. S2 (see supporting information), to show the couplings
resolved at a lower field. The doublet signals at 1.38 (J =
6.8 Hz) and 1.40 ppm (J = 6.9 Hz) belong to the protons of two
CH groups. Two multiplets, in the range 4.29–4.45 ppm,
appear for the two C—H protons of the chiral segments.
3
1
In the C NMR spectrum of L-1, the ‘dd’ signal of C3/C7,
3
1
3
i.e. the C atom bonded to fluorine, arises from J and J
couplings between the C and two Fatoms. The ipso-C atoms of
two (C H )CH(CH )(NH) groups are revealed at 146.24
6
5
3
3
3
(
atom of the 2,6-F -C H part appears as a triplet at
JC–P = 5.5 Hz) and 145.89 ppm ( J
= 5.6 Hz). The para-C
C–P
2
6
3
3
31.84 ppm, with JC–F = 19.2 Hz. The ipso-C atom of the 2,6-
1
F -C H part shows a ‘td’ pattern due to J
2
= 22.5 Hz from
the two F atoms and J = 8.4 Hz. The C4/C6 signal appears
2
6
3
C–F
Acknowledgements
3
C–P
Support of this investigation by Ferdowsi University of
Mashhad is gratefully acknowledged.
2
as a ‘dd’ pattern arising from J and J couplings with F atoms;
4
4
however, the J coupling is too weak and is not well resolved.
In the aliphatic region, the signals of the C—H units appear as
singlets, while the signals of the methyl groups appear as
Funding information
3
doublets (at 25.48 and 24.92 ppm, with J
respectively).
= 5.3 and 4.9 Hz,
Funding for this research was provided by: Ferdowsi Univer-
sity of Mashhad (award No. 3/42356); Czech Science Foun-
dation (grant No. 14-03276-S).
C–P
The mass spectra of both compounds reveal the presence of
the molecular ion peak at m/z = 443 in a 70 eV experiment.
The ion peaks at m/z 338, 141, 120 (base peak), and 105 belong
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McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem.
Commun. pp. 3814–3816.
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790.
Pet rˇ ı´ cˇ ek, V., Du sˇ ek, M. & Palatinus, L. (2014). Z. Kristallogr. 229,
Tarahhomi, A., Pourayoubi, M., Golen, J. A., Zargaran, P., Elahi, B.,
Rheingold, A. L., Leyva Ram ı´ rez, M. A. & Mancilla Percino, T.
(2013). Acta Cryst. B69, 260–270.
Vahdani Alviri, B., Pourayoubi, M., Saneei, A., Keikha, M., van der
Lee, A., Crochet, A., Ajees, A. A., Ne cˇ as, M., Fromm, K. M.,
Damodaran, K. & Jenny, T. A. (2018). Tetrahedron, 74, 28–41.
Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J.,
Jayatilaka, D. & Spackman, M. A. (2013). CrystalExplorer.
University of Western Australia.
345–352.
Pourayoubi, M., Ne cˇ as, M. & Negari, M. (2012). Acta Cryst. C68, o51–
o56.
Pourayoubi, M., Toghraee, M., Zhu, J., Du sˇ ek, M., Bereciartua, P. J. &
Eigner, V. (2014). CrystEngComm, 16, 10870–10887.
Zinna, F., Giovanella, U. & Di Bari, L. (2015). Adv. Mater. 27, 1791–
1795.
ꢂ
1
0 of 10 Eghbali Toularoud et al.
Two single-enantiomer phosphoric triamides
Acta Cryst. (2018). C74

supporting information
supporting information
Acta Cryst. (2018). C74 [https://doi.org/10.1107/S2053229618004734]
Chiral one-dimensional hydrogen-bonded architectures constructed from
single-enantiomer phosphoric triamides
Mahsa Eghbali Toularoud, Mehrdad Pourayoubi, Michal Dušek, Václav Eigner and Krishnan
Damodaran
Computing details
For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD,
2
2
2
015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: JANA2006 (Version
4/09/2015; Petříček et al., 2014); program(s) used to refine structure: JANA2006 (Version 24/09/2015; Petříček et al.,
014); molecular graphics: CrystalExplorer (Wolff et al., 2013); software used to prepare material for publication:
JANA2006 (Version 24/09/2015; Petříček et al., 2014), SUPERFLIP (Palatinus & Chapuis, 2007) and MCE2005
Rohlícek & Husák, 2007).
(
N-(2,6-Difluorobenzoyl)-N′,N′′-bis[(S)-(-)-α-methylbenzyl]phosphoric triamide (I)
Crystal data
C
23 24
H F
2 3 2
N O P
Z = 2
M
r
= 443.4
F(000) = 464
D = 1.334 Mg m
x
−3
Triclinic, P1
Hall symbol: P 1
a = 9.7608 (3) Å
b = 10.6134 (3) Å
c = 11.2721 (3) Å
α = 77.398 (2)°
β = 75.589 (2)°
γ = 87.635 (2)°
Cu Kα radiation, λ = 1.54184 Å
Cell parameters from 14044 reflections
θ = 4.1–67.2°
µ = 1.47 mm
T = 120 K
−1
Prism, colourless
0.53 × 0.19 × 0.08 mm
3
V = 1103.64 (6) Å
Data collection
Agilent Xcalibur/Gemini ultra
diffractometer with an AtlasS2 detector
Radiation source: X-ray tube
Mirror monochromator
Detector resolution: 5.1783 pixels mm
ω scans
21163 measured reflections
7492 independent reflections
6976 reflections with I > 3σ(I)
R
int = 0.051
-1
θmax = 67.2°, θmin = 4.2°
h = −11→11
k = −12→12
l = −13→13
Absorption correction: analytical
(CrysAlis PRO; Rigaku OD, 2015)
T
min = 0.562, Tmax = 0.896
Acta Cryst. (2018). C74
sup-1

supporting information
Refinement
2
Refinement on F
H atoms treated by a mixture of independent
R[F > 3σ(F)] = 0.047
wR(F) = 0.121
S = 1.71
and constrained refinement
Weighting scheme based on measured s.u.'s w =
2
2
1/(σ (I) + 0.0016I )
(Δ/σ)max = 0.038
7
5
6
1
492 reflections
78 parameters
restraints
−3
Δρmax = 0.30 e Å
Δρmin = −0.31 e Å
−3
77 constraints
Absolute structure: 3546 of Friedel pairs used in
the refinement
Absolute structure parameter: 0.014 (17)
2
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å )
x
y
z
Uiso*/Ueq
P1a
P1b
F1a
F2a
F1b
F2b
0.42969 (8)
0.93005 (8)
0.5086 (2)
0.3523 (2)
1.0313 (2)
0.8561 (3)
0.56352 (19)
0.2576 (2)
1.0676 (2)
0.7535 (2)
0.4696 (2)
0.3729 (2)
0.2950 (2)
0.9696 (3)
0.8565 (2)
0.8044 (2)
0.3791 (3)
0.4316 (3)
0.4958 (3)
0.5419 (4)
0.5248 (4)
0.4603 (4)
0.4152 (4)
0.4603 (3)
0.4546 (4)
0.4202 (3)
0.5229 (3)
0.4906 (4)
0.3523 (4)
0.2513 (4)
0.2839 (3)
0.3078 (3)
0.2456 (3)
0.2412 (3)
0.70347 (7)
0.70016 (7)
0.30564 (19)
0.3273 (2)
0.32193 (17)
0.2938 (2)
0.76047 (18)
0.4860 (2)
0.75981 (18)
0.4649 (2)
0.5453 (2)
0.7653 (2)
0.7135 (2)
0.5418 (2)
0.7539 (2)
0.7135 (2)
0.4570 (3)
0.3239 (3)
0.2516 (3)
0.1282 (3)
0.0723 (4)
0.1387 (4)
0.2616 (3)
0.7797 (3)
0.6600 (3)
0.8990 (3)
0.9569 (3)
1.0599 (4)
1.1058 (3)
1.0499 (3)
0.9467 (3)
0.7245 (3)
0.8532 (3)
0.6102 (3)
0.88573 (6)
0.87843 (6)
1.06091 (18)
0.69523 (18)
1.06766 (15)
0.7220 (2)
0.89095 (16)
0.8713 (2)
0.86840 (17)
0.8922 (2)
0.8883 (2)
0.7623 (2)
1.0014 (2)
0.8846 (2)
0.7637 (2)
0.9995 (2)
0.8789 (2)
0.8761 (3)
0.9652 (3)
0.9637 (4)
0.8694 (4)
0.7779 (4)
0.7837 (3)
0.6343 (2)
0.5804 (3)
0.5472 (2)
0.4419 (3)
0.3554 (3)
0.3731 (3)
0.4773 (3)
0.5650 (3)
1.1250 (2)
1.1517 (3)
1.2291 (2)
0.01478 (19)
0.0155 (2)
0.0402 (7)
0.0480 (8)
0.0316 (6)
0.0472 (8)
0.0186 (6)
0.0267 (7)
0.0199 (6)
0.0270 (7)
0.0193 (7)
0.0182 (7)
0.0191 (7)
0.0215 (8)
0.0195 (7)
0.0215 (8)
0.0192 (8)
0.0237 (9)
0.0323 (10)
0.0504 (15)
0.0557 (16)
0.0511 (15)
0.0342 (11)
0.0205 (9)
0.0327 (11)
0.0213 (9)
0.0322 (10)
0.0416 (12)
0.0396 (12)
0.0360 (11)
0.0282 (10)
0.0203 (9)
0.0293 (10)
0.0203 (9)
O1a
O2a
O1b
O2b
N1a
N2a
N3a
N1b
N2b
N3b
C1a
C2a
C3a
C4a
C5a
C6a
C7a
C8a
C9a
C10a
C11a
C12a
C13a
C14a
C15a
C16a
C17a
C18a
Acta Cryst. (2018). C74
sup-2

supporting information
C19a
C20a
C21a
C22a
C23a
C1b
C2b
C3b
C4b
C5b
C6b
C7b
C8b
C9b
C10b
C11b
C12b
C13b
C14b
C15b
C16b
C17b
C18b
C19b
C20b
C21b
C22b
C23b
H1n1a
H1n2a
H1n3a
H1n1b
H1n2b
H1n3b
H1c4a
H1c5a
H1c6a
H1c8a
H1c9a
H2c9a
H3c9a
H1c11a
H1c12a
H1c13a
H1c14a
H1c15a
H1c16a
H1c17a
0.1802 (3)
0.1256 (4)
0.1295 (4)
0.1914 (4)
0.2457 (3)
0.8781 (3)
0.9415 (3)
1.0192 (3)
1.0823 (3)
1.0669 (4)
0.9891 (4)
0.9289 (3)
0.9219 (3)
0.8700 (3)
0.8997 (3)
0.9569 (3)
0.9377 (3)
0.8602 (4)
0.8035 (4)
0.8221 (3)
0.8251 (3)
0.7811 (5)
0.7456 (3)
0.7849 (4)
0.7097 (4)
0.5930 (4)
0.5550 (4)
0.6310 (3)
0.5517 (16)
0.2832 (7)
0.2156 (17)
1.0552 (13)
0.7657 (3)
0.7227 (16)
0.585472
0.557726
0.447712
0.555862
0.509728
0.492292
0.358272
0.617653
0.562681
0.328311
0.5051 (3)
0.4021 (3)
0.4001 (3)
0.5041 (3)
0.6075 (3)
0.4461 (3)
0.3151 (3)
0.2573 (3)
0.1402 (3)
0.0719 (3)
0.1230 (3)
0.2418 (3)
0.7565 (3)
0.6444 (3)
0.8862 (3)
0.9079 (3)
1.0240 (3)
1.1209 (3)
1.1001 (3)
0.9846 (3)
0.6982 (3)
0.8217 (3)
0.5832 (3)
0.5382 (3)
0.4404 (3)
0.3847 (3)
0.4259 (3)
0.5237 (3)
0.519 (3)
0.754 (3)
0.725 (3)
0.521 (3)
0.752 (3)
0.727 (3)
0.081706
−0.013751
0.099488
0.790094
0.67571
1.2045 (3)
1.3009 (3)
1.4229 (3)
1.4479 (3)
1.3525 (3)
0.8914 (2)
0.8940 (3)
0.9789 (2)
0.9798 (3)
0.8914 (3)
0.8053 (3)
0.8085 (3)
0.6330 (2)
0.5896 (3)
0.5501 (2)
0.4211 (3)
0.3432 (3)
0.3922 (3)
0.5201 (3)
0.5983 (2)
1.1256 (2)
1.1726 (3)
1.2179 (2)
1.3303 (3)
1.4222 (3)
1.4044 (3)
1.2908 (3)
1.1992 (3)
0.897 (3)
0.775 (3)
0.981 (3)
0.887 (3)
0.788 (3)
0.984 (3)
1.027517
0.866686
0.712181
0.639283
0.49513
0.0271 (10)
0.0343 (11)
0.0341 (11)
0.0347 (11)
0.0300 (10)
0.0197 (9)
0.0217 (9)
0.0225 (9)
0.0304 (10)
0.0356 (11)
0.0419 (13)
0.0299 (10)
0.0216 (9)
0.0299 (10)
0.0210 (9)
0.0327 (10)
0.0342 (11)
0.0339 (11)
0.0326 (11)
0.0272 (9)
0.0254 (10)
0.0446 (13)
0.0233 (9)
0.0341 (11)
0.0421 (13)
0.0406 (12)
0.0370 (11)
0.0281 (10)
0.0232*
0.0219*
0.0229*
0.0258*
0.0234*
0.0258*
0.0605*
0.0668*
0.0613*
0.0246*
0.0392*
0.0392*
0.0392*
0.0387*
0.05*
0.0475*
0.0432*
0.58757
0.629251
0.583119
0.429132
0.283514
0.312557
0.489927
0.637905
1.1241
0.641667
0.924764
1.099817
1.176165
1.082278
0.908615
0.72268
0.156687
0.212086
0.406511
0.0338*
0.0243*
0.0352*
0.255892
0.862125
1.231992
Acta Cryst. (2018). C74
sup-3

supporting information
H2c17a
H3c17a
H1c19a
H1c20a
H1c21a
H1c22a
H1c23a
H1c4b
H1c5b
H1c6b
H1c8b
H1c9b
0.294717
0.147048
0.176156
0.083993
0.090281
0.196098
0.287364
1.136127
1.11031
0.977386
1.021704
0.922789
0.883182
0.771347
1.010646
0.978358
0.846
0.750284
0.781179
0.923797
0.791586
0.839945
0.684089
0.865845
0.738611
0.538781
0.475878
0.604158
0.922963
0.855228
0.504521
0.33035
0.328179
0.503706
0.67901
1.087811
1.152057
1.120374
1.282784
1.489352
1.532064
1.371072
1.039828
0.890171
0.744438
0.624882
0.505619
0.644478
0.591375
0.385657
0.254574
0.338293
0.555186
0.686835
1.120119
1.256696
1.119104
1.171712
1.344067
1.498953
1.469283
1.276321
1.121233
0.0352*
0.0352*
0.0326*
0.0412*
0.0409*
0.0416*
0.036*
0.0365*
0.0427*
0.0503*
0.0259*
0.0358*
0.0358*
0.0358*
0.0392*
0.0411*
0.0407*
0.0392*
0.0326*
0.0304*
0.0535*
0.0535*
0.0535*
0.041*
0.105687
−0.010774
0.076233
0.746021
0.643642
0.564432
0.654769
0.841365
1.037267
1.201279
1.167145
0.971916
0.682112
0.811117
0.892379
0.839455
0.575859
0.410967
0.318605
0.386164
0.550906
H2c9b
H3c9b
H1c11b
H1c12b
H1c13b
H1c14b
H1c15b
H1c16b
H1c17b
H2c17b
H3c17b
H1c19b
H1c20b
H1c21b
H1c22b
H1c23b
0.0505*
0.0488*
0.0444*
0.0337*
2
Atomic displacement parameters (Å )
11
22
33
12
13
23
U
U
U
U
U
U
P1a
P1b
F1a
F2a
F1b
F2b
O1a
O2a
O1b
O2b
N1a
N2a
N3a
N1b
N2b
N3b
0.0129 (3)
0.0137 (3)
0.0465 (11)
0.0647 (14)
0.0435 (11)
0.0636 (14)
0.0158 (9)
0.0179 (10)
0.0160 (9)
0.0183 (10)
0.0166 (11)
0.0146 (11)
0.0116 (10)
0.0160 (11)
0.0165 (11)
0.0158 (11)
0.0149 (3)
0.0164 (3)
0.0335 (11)
0.0466 (13)
0.0275 (9)
0.0430 (12)
0.0164 (9)
0.0259 (11)
0.0195 (10)
0.0243 (11)
0.0168 (12)
0.0214 (12)
0.0260 (13)
0.0188 (12)
0.0225 (12)
0.0308 (13)
0.0189 (3)
0.0016 (2)
0.0015 (2)
0.0007 (9)
−0.0048 (11)
0.0067 (8)
0.0098 (11)
0.0022 (7)
0.0039 (8)
0.0010 (8)
0.0014 (9)
0.0010 (9)
0.0017 (9)
0.0045 (9)
0.0001 (10)
0.0035 (10)
0.0050 (10)
−0.0083 (2)
−0.0091 (2)
−0.0264 (9)
−0.0213 (10)
−0.0226 (8)
−0.0432 (11)
−0.0101 (7)
−0.0150 (8)
−0.0112 (7)
−0.0143 (8)
−0.0120 (9)
−0.0102 (9)
−0.0097 (8)
−0.0135 (10)
−0.0117 (9)
−0.0109 (9)
−0.0036 (2)
−0.0035 (2)
0.0017 (8)
0.0191 (3)
0.0442 (10)
0.0428 (11)
0.0320 (8)
0.0550 (12)
0.0261 (9)
0.0418 (11)
0.0274 (9)
0.0417 (11)
0.0275 (11)
0.0214 (10)
0.0230 (11)
0.0326 (11)
0.0229 (11)
0.0210 (11)
−0.0211 (9)
−0.0098 (7)
−0.0212 (9)
−0.0045 (7)
−0.0109 (9)
−0.0051 (7)
−0.0064 (8)
−0.0037 (9)
−0.0040 (9)
−0.0069 (9)
−0.0034 (9)
−0.0048 (9)
−0.0060 (9)
Acta Cryst. (2018). C74
sup-4

supporting information
C1a
C2a
C3a
C4a
C5a
C6a
C7a
C8a
0.0167 (13)
0.0191 (13)
0.0245 (15)
0.039 (2)
0.041 (2)
0.051 (2)
0.0332 (17)
0.0207 (14)
0.054 (2)
0.0232 (14)
0.0301 (16)
0.041 (2)
0.0175 (14)
0.0165 (14)
0.0210 (15)
0.0206 (18)
0.0179 (18)
0.031 (2)
0.0282 (17)
0.0213 (14)
0.0222 (16)
0.0221 (14)
0.0335 (17)
0.040 (2)
0.0245 (12)
0.0345 (14)
0.0460 (17)
0.081 (3)
0.090 (3)
0.068 (3)
0.0 (11)
−0.0072 (10)
−0.0039 (11)
−0.0072 (13)
−0.0086 (19)
0.013 (2)
−0.0046 (10)
−0.0066 (11)
0.0025 (12)
0.0048 (17)
−0.0085 (19)
−0.0286 (18)
−0.0144 (13)
−0.0051 (10)
−0.0086 (11)
−0.0072 (10)
−0.0029 (12)
0.0085 (14)
0.0077 (13)
0.0043 (13)
0.0027 (11)
−0.0052 (10)
−0.0063 (11)
−0.0038 (10)
−0.0064 (11)
−0.0056 (12)
0.0056 (12)
−0.0020 (12)
−0.0059 (11)
−0.0040 (10)
−0.0061 (11)
−0.0055 (10)
−0.0005 (12)
−0.0102 (13)
−0.0208 (15)
−0.0117 (12)
−0.0092 (11)
−0.0103 (11)
−0.0053 (11)
−0.0074 (12)
0.0014 (12)
0.0052 (12)
−0.0059 (12)
−0.0054 (11)
−0.0088 (11)
−0.0126 (13)
−0.0084 (11)
−0.0099 (12)
−0.0063 (13)
0.0021 (12)
−0.0014 (14)
−0.0021 (12)
−0.0002 (11)
0.0011 (13)
0.0037 (16)
0.0035 (16)
−0.0104 (18)
−0.0043 (14)
0.0034 (11)
0.0086 (14)
0.0010 (12)
0.0011 (13)
−0.0029 (16)
0.0028 (16)
0.0025 (14)
−0.0011 (12)
0.0003 (11)
0.0002 (13)
0.0063 (11)
−0.0003 (13)
−0.0031 (14)
0.0005 (14)
0.0029 (15)
0.0010 (13)
0.0005 (11)
−0.0005 (12)
−0.0009 (11)
0.0032 (13)
0.0050 (14)
0.0010 (16)
0.0013 (13)
0.0048 (11)
0.0045 (13)
−0.0012 (11)
0.0023 (14)
−0.0049 (15)
−0.0074 (14)
0.0020 (14)
−0.0006 (13)
−0.0012 (13)
−0.0144 (18)
0.0080 (12)
0.0092 (15)
0.0147 (18)
0.0093 (16)
0.0007 (15)
0.0043 (13)
0.0102 (19)
0.0001 (14)
0.0401 (17)
0.0221 (12)
0.0268 (13)
0.0225 (12)
0.0317 (14)
0.0334 (16)
0.0431 (17)
0.0485 (18)
0.0330 (14)
0.0186 (12)
0.0245 (13)
0.0233 (12)
0.0290 (14)
0.0377 (16)
0.0314 (15)
0.0239 (14)
0.0251 (13)
0.0242 (12)
0.0280 (13)
0.0248 (12)
0.0364 (15)
0.0459 (17)
0.0495 (19)
0.0372 (15)
0.0233 (12)
0.0302 (14)
0.0218 (12)
0.0248 (13)
0.0222 (13)
0.0328 (15)
0.0328 (15)
0.0220 (13)
0.0186 (12)
0.0310 (16)
0.0217 (12)
0.0271 (14)
0.0264 (15)
0.0296 (15)
0.0418 (16)
0.0286 (14)
−0.0103 (11)
−0.0164 (13)
−0.0106 (11)
−0.0088 (12)
−0.0046 (14)
−0.0236 (15)
−0.0182 (14)
−0.0118 (12)
−0.0104 (10)
−0.0032 (12)
−0.0086 (10)
−0.0143 (12)
−0.0128 (14)
−0.0084 (13)
−0.0115 (12)
−0.0140 (12)
−0.0089 (10)
−0.0094 (11)
−0.0075 (11)
−0.0108 (13)
−0.0052 (15)
−0.0182 (17)
−0.0187 (13)
−0.0117 (11)
−0.0166 (12)
−0.0106 (10)
−0.0052 (12)
−0.0067 (12)
−0.0192 (13)
−0.0135 (13)
−0.0094 (11)
−0.0109 (11)
−0.0050 (16)
−0.0088 (11)
−0.0220 (14)
−0.0222 (16)
−0.0053 (15)
−0.0097 (14)
−0.0135 (12)
C9a
C10a
C11a
C12a
C13a
C14a
C15a
C16a
C17a
C18a
C19a
C20a
C21a
C22a
C23a
C1b
C2b
C3b
C4b
C5b
C6b
C7b
C8b
C9b
C10b
C11b
C12b
C13b
C14b
C15b
C16b
C17b
C18b
C19b
C20b
C21b
C22b
C23b
0.047 (2)
0.0285 (19)
0.0281 (18)
0.0250 (16)
0.0244 (15)
0.0236 (15)
0.0216 (15)
0.0251 (15)
0.0276 (17)
0.0285 (17)
0.0393 (19)
0.0324 (17)
0.0190 (14)
0.0197 (15)
0.0209 (14)
0.0226 (16)
0.0195 (16)
0.0312 (19)
0.0259 (16)
0.0253 (15)
0.0260 (16)
0.0271 (15)
0.0410 (18)
0.0410 (19)
0.0302 (17)
0.0256 (16)
0.0294 (16)
0.0383 (18)
0.0351 (19)
0.0268 (16)
0.0337 (18)
0.0321 (19)
0.0265 (17)
0.0312 (18)
0.0307 (17)
0.0298 (17)
0.0249 (15)
0.0211 (13)
0.0379 (17)
0.0171 (13)
0.0315 (16)
0.0391 (18)
0.0367 (17)
0.0404 (18)
0.0357 (16)
0.0175 (14)
0.0200 (13)
0.0229 (14)
0.0306 (16)
0.0396 (19)
0.054 (2)
0.0342 (17)
0.0210 (13)
0.0394 (17)
0.0174 (13)
0.0314 (16)
0.0359 (17)
0.0395 (18)
0.0416 (18)
0.0317 (15)
0.0237 (14)
0.068 (3)
0.0238 (14)
0.049 (2)
0.072 (3)
0.058 (2)
0.0350 (17)
0.0264 (15)
Acta Cryst. (2018). C74
sup-5

supporting information
Geometric parameters (Å, º)
P1a—O1a
P1a—N1a
P1a—N2a
P1a—N3a
P1b—O1b
P1b—N1b
P1b—N2b
P1b—N3b
F1a—C3a
1.481 (2)
1.703 (2)
1.621 (2)
1.624 (2)
1.477 (2)
1.699 (3)
1.619 (3)
1.620 (2)
1.361 (5)
1.351 (4)
1.359 (4)
1.355 (4)
1.232 (3)
1.223 (3)
1.351 (4)
0.86 (2)
1.461 (3)
0.860 (9)
1.459 (4)
0.86 (2)
1.358 (4)
0.860 (17)
1.447 (3)
0.860 (14)
1.458 (4)
0.86 (2)
1.487 (4)
1.389 (5)
1.392 (5)
1.369 (5)
1.372 (7)
0.96
C17a—H2c17a
C17a—H3c17a
C18a—C19a
C18a—C23a
C19a—C20a
C19a—H1c19a
C20a—C21a
C20a—H1c20a
C21a—C22a
C21a—H1c21a
C22a—C23a
C22a—H1c22a
C23a—H1c23a
C1b—C2b
C2b—C3b
C2b—C7b
C3b—C4b
C4b—C5b
C4b—H1c4b
C5b—C6b
C5b—H1c5b
C6b—C7b
C6b—H1c6b
C8b—C9b
C8b—C10b
C8b—H1c8b
C9b—H1c9b
C9b—H2c9b
C9b—H3c9b
C10b—C11b
C10b—C15b
C11b—C12b
C11b—H1c11b
C12b—C13b
C12b—H1c12b
C13b—C14b
C13b—H1c13b
C14b—C15b
C14b—H1c14b
C15b—H1c15b
C16b—C17b
C16b—C18b
C16b—H1c16b
C17b—H1c17b
C17b—H2c17b
C17b—H3c17b
0.96
0.96
1.396 (5)
1.397 (4)
1.378 (4)
0.96
1.381 (5)
0.9599
1.393 (5)
0.96
F2a—C7a
F1b—C3b
F2b—C7b
1.375 (4)
0.96
O2a—C1a
O2b—C1b
N1a—C1a
N1a—H1n1a
N2a—C8a
N2a—H1n2a
N3a—C16a
N3a—H1n3a
N1b—C1b
N1b—H1n1b
N2b—C8b
N2b—H1n2b
N3b—C16b
N3b—H1n3b
C1a—C2a
C2a—C3a
C2a—C7a
C3a—C4a
C4a—C5a
C4a—H1c4a
C5a—C6a
C5a—H1c5a
C6a—C7a
C6a—H1c6a
C8a—C9a
0.9601
1.495 (4)
1.391 (4)
1.395 (5)
1.363 (4)
1.393 (5)
0.96
1.385 (6)
0.96
1.373 (5)
0.96
1.529 (5)
1.526 (4)
0.96
0.96
0.96
0.96
1.393 (4)
1.392 (4)
1.384 (4)
0.96
1.383 (5)
0.96
1.381 (4)
0.96
1.380 (4)
0.96
1.387 (7)
0.96
1.369 (5)
0.96
1.531 (5)
1.526 (4)
0.9601
0.96
0.96
0.9599
C8a—C10a
C8a—H1c8a
C9a—H1c9a
C9a—H2c9a
C9a—H3c9a
C10a—C11a
C10a—C15a
C11a—C12a
C11a—H1c11a
0.96
1.526 (5)
1.516 (4)
0.96
0.96
0.96
1.390 (4)
1.387 (4)
1.380 (5)
0.96
0.96
Acta Cryst. (2018). C74
sup-6

supporting information
C12a—C13a
C12a—H1c12a
C13a—C14a
C13a—H1c13a
C14a—C15a
C14a—H1c14a
C15a—H1c15a
C16a—C17a
1.398 (5)
0.96
1.367 (4)
0.96
1.391 (4)
0.96
0.96
1.532 (4)
1.528 (3)
0.9601
0.96
C18b—C19b
C18b—C23b
C19b—C20b
C19b—H1c19b
C20b—C21b
C20b—H1c20b
C21b—C22b
C21b—H1c21b
C22b—C23b
C22b—H1c22b
C23b—H1c23b
1.394 (4)
1.389 (5)
1.380 (4)
0.9601
1.382 (6)
0.96
1.395 (5)
0.96
1.381 (4)
0.9599
0.96
C16a—C18a
C16a—H1c16a
C17a—H1c17a
O1a—P1a—N1a
O1a—P1a—N2a
O1a—P1a—N3a
N1a—P1a—N2a
N1a—P1a—N3a
N2a—P1a—N3a
O1b—P1b—N1b
O1b—P1b—N2b
O1b—P1b—N3b
N1b—P1b—N2b
N1b—P1b—N3b
N2b—P1b—N3b
P1a—N1a—C1a
P1a—N1a—H1n1a
C1a—N1a—H1n1a
P1a—N2a—C8a
P1a—N2a—H1n2a
C8a—N2a—H1n2a
P1a—N3a—C16a
P1a—N3a—H1n3a
C16a—N3a—H1n3a
P1b—N1b—C1b
P1b—N1b—H1n1b
C1b—N1b—H1n1b
P1b—N2b—C8b
P1b—N2b—H1n2b
C8b—N2b—H1n2b
P1b—N3b—C16b
P1b—N3b—H1n3b
C16b—N3b—H1n3b
O2a—C1a—N1a
O2a—C1a—C2a
N1a—C1a—C2a
C1a—C2a—C3a
C1a—C2a—C7a
C3a—C2a—C7a
103.50 (12)
115.22 (11)
115.23 (13)
109.74 (13)
109.45 (11)
103.69 (12)
103.20 (12)
116.02 (11)
116.30 (13)
109.56 (14)
109.49 (12)
102.25 (12)
124.0 (2)
119 (2)
117 (2)
123.39 (19)
113 (2)
118 (2)
123.52 (19)
114 (2)
122 (2)
126.2 (2)
116 (2)
118 (2)
125.02 (19)
113 (2)
118 (2)
123.6 (2)
114 (2)
C18a—C19a—C20a
120.1 (3)
119.96
119.97
121.4 (3)
119.3
119.3
118.8 (3)
120.59
120.59
120.2 (3)
119.88
C18a—C19a—H1c19a
C20a—C19a—H1c19a
C19a—C20a—C21a
C19a—C20a—H1c20a
C21a—C20a—H1c20a
C20a—C21a—C22a
C20a—C21a—H1c21a
C22a—C21a—H1c21a
C21a—C22a—C23a
C21a—C22a—H1c22a
C23a—C22a—H1c22a
C18a—C23a—C22a
C18a—C23a—H1c23a
C22a—C23a—H1c23a
O2b—C1b—N1b
O2b—C1b—C2b
N1b—C1b—C2b
C1b—C2b—C3b
C1b—C2b—C7b
C3b—C2b—C7b
F1b—C3b—C2b
F1b—C3b—C4b
C2b—C3b—C4b
119.87
121.1 (3)
119.46
119.46
123.0 (3)
121.8 (3)
115.1 (2)
123.6 (3)
121.8 (3)
114.5 (3)
117.4 (3)
118.2 (3)
124.4 (3)
118.4 (3)
120.78
120.78
120.1 (3)
119.93
119.94
118.8 (4)
120.62
C3b—C4b—C5b
C3b—C4b—H1c4b
C5b—C4b—H1c4b
C4b—C5b—C6b
C4b—C5b—H1c5b
C6b—C5b—H1c5b
C5b—C6b—C7b
C5b—C6b—H1c6b
C7b—C6b—H1c6b
F2b—C7b—C2b
123 (2)
121.2 (3)
120.9 (3)
117.9 (2)
123.4 (3)
121.3 (3)
115.2 (3)
120.62
117.4 (3)
118.9 (3)
123.7 (3)
F2b—C7b—C6b
C2b—C7b—C6b
Acta Cryst. (2018). C74
sup-7

supporting information
F1a—C3a—C2a
F1a—C3a—C4a
C2a—C3a—C4a
C3a—C4a—C5a
C3a—C4a—H1c4a
C5a—C4a—H1c4a
C4a—C5a—C6a
C4a—C5a—H1c5a
C6a—C5a—H1c5a
C5a—C6a—C7a
C5a—C6a—H1c6a
C7a—C6a—H1c6a
F2a—C7a—C2a
117.7 (3)
118.9 (3)
123.4 (4)
118.8 (4)
120.59
120.6
120.7 (4)
119.62
N2b—C8b—C9b
111.8 (2)
111.1 (2)
107.37
111.3 (2)
107.17
107.86
109.47
109.47
109.47
109.47
109.47
109.48
119.6 (3)
122.4 (2)
118.0 (3)
121.0 (3)
119.49
119.49
120.4 (3)
119.78
119.78
118.8 (3)
120.59
120.59
121.0 (3)
119.48
119.49
120.7 (2)
119.66
119.66
109.1 (2)
113.4 (3)
107.21
110.0 (2)
110.75
106.25
109.47
109.47
109.47
N2b—C8b—C10b
N2b—C8b—H1c8b
C9b—C8b—C10b
C9b—C8b—H1c8b
C10b—C8b—H1c8b
C8b—C9b—H1c9b
C8b—C9b—H2c9b
C8b—C9b—H3c9b
H1c9b—C9b—H2c9b
H1c9b—C9b—H3c9b
H2c9b—C9b—H3c9b
C8b—C10b—C11b
C8b—C10b—C15b
C11b—C10b—C15b
C10b—C11b—C12b
C10b—C11b—H1c11b
C12b—C11b—H1c11b
C11b—C12b—C13b
C11b—C12b—H1c12b
C13b—C12b—H1c12b
C12b—C13b—C14b
C12b—C13b—H1c13b
C14b—C13b—H1c13b
C13b—C14b—C15b
C13b—C14b—H1c14b
C15b—C14b—H1c14b
C10b—C15b—C14b
C10b—C15b—H1c15b
C14b—C15b—H1c15b
N3b—C16b—C17b
119.63
118.3 (4)
120.84
120.84
117.6 (3)
118.9 (4)
123.5 (3)
112.6 (2)
111.5 (2)
105.99
109.9 (2)
107.72
108.89
109.47
109.47
109.47
109.47
F2a—C7a—C6a
C2a—C7a—C6a
N2a—C8a—C9a
N2a—C8a—C10a
N2a—C8a—H1c8a
C9a—C8a—C10a
C9a—C8a—H1c8a
C10a—C8a—H1c8a
C8a—C9a—H1c9a
C8a—C9a—H2c9a
C8a—C9a—H3c9a
H1c9a—C9a—H2c9a
H1c9a—C9a—H3c9a
H2c9a—C9a—H3c9a
C8a—C10a—C11a
C8a—C10a—C15a
C11a—C10a—C15a
C10a—C11a—C12a
C10a—C11a—H1c11a
C12a—C11a—H1c11a
C11a—C12a—C13a
C11a—C12a—H1c12a
C13a—C12a—H1c12a
C12a—C13a—C14a
C12a—C13a—H1c13a
C14a—C13a—H1c13a
C13a—C14a—C15a
C13a—C14a—H1c14a
C15a—C14a—H1c14a
C10a—C15a—C14a
C10a—C15a—H1c15a
C14a—C15a—H1c15a
N3a—C16a—C17a
N3a—C16a—C18a
N3a—C16a—H1c16a
109.48
109.48
118.3 (2)
122.6 (2)
119.0 (3)
121.0 (3)
119.53
119.52
119.5 (3)
120.22
120.23
119.6 (3)
120.18
120.18
120.9 (3)
119.55
N3b—C16b—C18b
N3b—C16b—H1c16b
C17b—C16b—C18b
C17b—C16b—H1c16b
C18b—C16b—H1c16b
C16b—C17b—H1c17b
C16b—C17b—H2c17b
C16b—C17b—H3c17b
H1c17b—C17b—H2c17b
H1c17b—C17b—H3c17b
H2c17b—C17b—H3c17b
C16b—C18b—C19b
C16b—C18b—C23b
C19b—C18b—C23b
C18b—C19b—C20b
C18b—C19b—H1c19b
C20b—C19b—H1c19b
109.47
109.47
109.47
118.5 (3)
123.4 (3)
118.0 (3)
121.2 (4)
119.39
119.56
119.9 (2)
120.03
120.03
109.0 (2)
113.1 (2)
108.16
119.39
Acta Cryst. (2018). C74
sup-8

supporting information
C17a—C16a—C18a
111.8 (2)
109.5
C19b—C20b—C21b
120.4 (3)
C17a—C16a—H1c16a
C18a—C16a—H1c16a
C16a—C17a—H1c17a
C16a—C17a—H2c17a
C16a—C17a—H3c17a
H1c17a—C17a—H2c17a
H1c17a—C17a—H3c17a
H2c17a—C17a—H3c17a
C16a—C18a—C19a
C19b—C20b—H1c20b
C21b—C20b—H1c20b
C20b—C21b—C22b
C20b—C21b—H1c21b
C22b—C21b—H1c21b
C21b—C22b—C23b
C21b—C22b—H1c22b
C23b—C22b—H1c22b
C18b—C23b—C22b
C18b—C23b—H1c23b
C22b—C23b—H1c23b
119.82
119.83
119.1 (3)
120.45
120.46
120.2 (4)
119.9
105.08
109.47
109.47
109.47
109.47
109.47
109.47
122.1 (3)
119.5 (3)
118.4 (2)
119.9
121.1 (3)
119.45
119.46
C16a—C18a—C23a
C19a—C18a—C23a
P1a—N2a—C8a—C9a
P1b—N2b—C8b—C9b
P1a—N3a—C16a—C17a
P1b—N3b—C16b—C17b
O1a—P1a—N1a—C1a
O1b—P1b—N1b—C1b
O1a—P1a—N2a—C8a
O1b—P1b—N2b—C8b
88.4 (3)
O1a—P1a—N3a—C16a
O1b—P1b—N3b—C16b
P1a—N1a—C1a—O2a
P1b—N1b—C1b—O2b
P1a—N2a—C8a—C10a
P1b—N2b—C8b—C10b
P1a—N3a—C16a—C18a
P1b—N3b—C16b—C18b
−25.2 (3)
−41.6 (3)
−2.2 (3)
100.4 (3)
117.7 (2)
121.6 (3)
−176.68 (19)
−178.4 (2)
51.6 (3)
1.0 (3)
−147.5 (2)
−134.6 (2)
−117.2 (2)
−115.4 (2)
55.9 (3)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
N1a—H1n1a···O2b
N2a—H1n2a···O1b
0.86 (2)
0.860 (9)
0.86 (2)
0.860 (17)
0.860 (14)
0.86 (2)
0.96
2.019 (18)
2.111 (11)
2.12 (3)
1.967 (15)
2.036 (13)
2.06 (3)
2.874 (3)
2.919 (3)
2.942 (3)
2.822 (3)
2.868 (3)
2.888 (3)
3.278 (4)
172 (3)
156 (3)
160 (3)
173 (3)
163 (3)
163 (3)
162.01
i
i
N3a—H1n3a···O1b
N1b—H1n1b···O2a
ii
N2b—H1n2b···O1a
N3b—H1n3b···O1a
iii
C5a—H1c5a···O1a
2.35
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x, y−1, z.
N-(2,6-Difluorobenzoyl)-N′,N′′-bis[(R)-(+)-α-methylbenzyl]phosphoric triamide (II)
Crystal data
C
23 24
H F
2 3 2
N O P
Z = 2
M
r
= 443.4
F(000) = 464
D = 1.338 Mg m
x
−3
Triclinic, P1
Hall symbol: P 1
a = 9.7524 (2) Å
b = 10.6117 (2) Å
c = 11.2510 (2) Å
α = 77.3381 (15)°
β = 75.6221 (16)°
γ = 87.7313 (16)°
V = 1100.33 (4) Å
Cu Kα radiation, λ = 1.54184 Å
Cell parameters from 12269 reflections
θ = 4.1–69.2°
µ = 1.46 mm
T = 95 K
−1
Prism, colourless
0.29 × 0.09 × 0.07 mm
3
Acta Cryst. (2018). C74
sup-9

supporting information
Data collection
Agilent SuperNova Dual Source
diffractometer with an AtlasS2 detector
Radiation source: X-ray tube
Mirror monochromator
Detector resolution: 5.2027 pixels mm
ω scans
16006 measured reflections
7660 independent reflections
7383 reflections with I > 3σ(I)
R
int = 0.034
-1
θmax = 69.4°, θmin = 4.2°
h = −10→11
k = −12→12
l = −13→13
Absorption correction: analytical
(CrysAlis PRO; Rigaku OD, 2015)
T
min = 0.774, Tmax = 0.917
Refinement
2
Refinement on F
H atoms treated by a mixture of independent
and constrained refinement
Weighting scheme based on measured s.u.'s w =
R[F > 3σ(F)] = 0.039
wR(F) = 0.098
S = 1.50
2
2
1/(σ (I) + 0.0016I )
(Δ/σ)max = 0.030
7
5
6
1
660 reflections
78 parameters
restraints
−3
Δρmax = 0.17 e Å
Δρmin = −0.22 e Å
−3
77 constraints
Absolute structure: 3604 of Friedel pairs used in
the refinement
Absolute structure parameter: −0.014 (14)
2
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å )
x
y
z
Uiso*/Ueq
P1a
P1b
F1a
F2a
F1b
F2b
O1a
O2a
O1b
O2b
N1a
N2a
N3a
N1b
N2b
N3b
C1a
C2a
C3a
C4a
C5a
C6a
C7a
C8a
C9a
0.56995 (6)
0.06956 (6)
0.49063 (16)
0.64829 (18)
−0.03241 (15)
0.14485 (18)
0.43627 (16)
0.74221 (16)
−0.06848 (16)
0.24662 (16)
0.52918 (19)
0.62725 (19)
0.70464 (19)
0.02925 (19)
0.14445 (19)
0.1948 (2)
0.6214 (2)
0.5677 (2)
0.5037 (3)
0.4576 (3)
0.4753 (3)
0.5401 (3)
0.5858 (3)
0.5386 (2)
0.29619 (5)
0.29985 (5)
0.69491 (13)
0.67228 (15)
0.67855 (12)
0.70701 (14)
0.23908 (13)
0.51377 (14)
0.23999 (13)
0.53595 (14)
0.45461 (16)
0.23425 (16)
0.28615 (17)
0.45795 (17)
0.24619 (16)
0.28665 (18)
0.5421 (2)
0.6759 (2)
0.7481 (2)
0.8722 (2)
0.9279 (2)
0.8611 (2)
0.7377 (2)
0.21972 (19)
0.3396 (2)
0.11407 (5)
0.12175 (5)
−0.06133 (13)
0.30505 (13)
−0.06760 (12)
0.27756 (15)
0.10831 (13)
0.12918 (15)
0.13222 (13)
0.10757 (15)
0.11171 (16)
0.23755 (15)
−0.00128 (16)
0.11576 (17)
0.23590 (16)
0.00034 (16)
0.12087 (19)
0.1237 (2)
0.01258 (15)
0.01314 (15)
0.0322 (5)
0.0384 (6)
0.0244 (4)
0.0376 (6)
0.0161 (5)
0.0215 (5)
0.0171 (5)
0.0220 (5)
0.0156 (5)
0.0151 (5)
0.0161 (5)
0.0170 (6)
0.0156 (5)
0.0175 (6)
0.0164 (6)
0.0201 (7)
0.0263 (8)
0.0398 (10)
0.0465 (11)
0.0404 (10)
0.0283 (8)
0.0171 (7)
0.0258 (8)
0.0341 (2)
0.0364 (3)
0.1307 (3)
0.2227 (3)
0.2164 (2)
0.36624 (18)
0.4199 (2)
0.5444 (3)
Acta Cryst. (2018). C74
sup-10

supporting information
C10a
C11a
C12a
C13a
C14a
C15a
C16a
C17a
C18a
C19a
C20a
C21a
C22a
C23a
C1b
C2b
C3b
C4b
C5b
C6b
C7b
C8b
C9b
C10b
C11b
C12b
C13b
C14b
C15b
C16b
C17b
C18b
C19b
C20b
C21b
C22b
C23b
H1c4a
H1c5a
H1c6a
H1c8a
H1c9a
H2c9a
H3c9a
H1c11a
H1c12a
H1c13a
H1c14a
0.5794 (2)
0.4765 (3)
0.5104 (3)
0.6473 (3)
0.7496 (3)
0.7155 (2)
0.6926 (2)
0.7548 (3)
0.7592 (2)
0.8193 (2)
0.8750 (3)
0.8718 (3)
0.8103 (3)
0.7555 (2)
0.1223 (2)
0.0578 (2)
−0.0204 (2)
−0.0835 (3)
−0.0678 (3)
0.0107 (3)
0.0715 (3)
0.0778 (2)
0.1309 (3)
0.1009 (2)
0.0436 (3)
0.0627 (3)
0.1401 (3)
0.1980 (3)
0.1790 (2)
0.1742 (2)
0.2172 (3)
0.2550 (2)
0.2153 (3)
0.2915 (3)
0.4089 (3)
0.4476 (3)
0.3701 (3)
0.413696
0.44259
0.10097 (19)
0.0426 (2)
−0.0605 (2)
−0.1063 (2)
−0.0495 (2)
0.0531 (2)
0.27494 (19)
0.1462 (2)
0.38947 (19)
0.4951 (2)
0.5991 (2)
0.6005 (2)
0.4961 (2)
0.3923 (2)
0.5539 (2)
0.68541 (19)
0.7421 (2)
0.8603 (2)
0.9280 (2)
0.8774 (2)
0.7579 (2)
0.24297 (19)
0.3555 (2)
0.1136 (2)
0.0910 (2)
−0.0255 (2)
−0.1223 (2)
−0.1008 (2)
0.0156 (2)
0.3030 (2)
0.1792 (2)
0.4184 (2)
0.4637 (2)
0.5613 (2)
0.6167 (2)
0.5742 (2)
0.4758 (2)
0.919017
0.45365 (18)
0.5600 (2)
0.6464 (2)
0.6292 (2)
0.5234 (2)
0.4358 (2)
−0.12562 (18)
−0.1518 (2)
−0.22965 (19)
−0.2049 (2)
−0.3023 (2)
−0.4246 (2)
−0.4499 (2)
−0.3536 (2)
0.10859 (18)
0.1059 (2)
0.02101 (19)
0.0210 (2)
0.1089 (2)
0.1950 (2)
0.1917 (2)
0.36791 (18)
0.4108 (2)
0.45054 (19)
0.5800 (2)
0.6578 (2)
0.6088 (2)
0.4801 (2)
0.40209 (19)
−0.12632 (19)
−0.1735 (2)
−0.21891 (19)
−0.3311 (2)
−0.4233 (2)
−0.4052 (2)
−0.2924 (2)
−0.1995 (2)
−0.027196
0.133401
0.0173 (7)
0.0256 (7)
0.0330 (8)
0.0312 (8)
0.0285 (8)
0.0224 (7)
0.0167 (6)
0.0234 (7)
0.0176 (7)
0.0212 (7)
0.0275 (8)
0.0275 (8)
0.0272 (8)
0.0235 (7)
0.0166 (7)
0.0177 (7)
0.0187 (7)
0.0246 (7)
0.0281 (8)
0.0327 (9)
0.0246 (8)
0.0178 (7)
0.0253 (7)
0.0178 (7)
0.0260 (7)
0.0277 (8)
0.0270 (8)
0.0267 (8)
0.0218 (7)
0.0214 (7)
0.0365 (9)
0.0196 (7)
0.0269 (8)
0.0337 (9)
0.0334 (9)
0.0298 (8)
0.0238 (7)
0.0478*
1.013983
0.900101
0.208923
0.324487
0.357035
0.412272
0.074289
−0.100546
−0.17667
0.0559*
0.0484*
0.0205*
0.0309*
0.0309*
0.0309*
0.0308*
0.0396*
0.552669
0.443119
0.288714
0.361198
0.504835
0.418827
0.36983
0.573319
0.718595
0.690061
0.487622
0.640552
0.508482
0.381568
0.438556
0.671006
0.844563
0.0375*
0.0342*
−0.081291
0.510522
Acta Cryst. (2018). C74
sup-11

supporting information
H1c15a
H1c16a
H1c17a
H2c17a
H3c17a
H1c19a
H1c20a
H1c21a
H1c22a
H1c23a
H1c4b
H1c5b
H1c6b
H1c8b
H1c9b
H2c9b
H3c9b
H1c11b
H1c12b
H1c13b
H1c14b
H1c15b
H1c16b
H1c17b
H2c17b
H3c17b
H1c19b
H1c20b
H1c21b
H1c22b
H1c23b
H1n1a
0.786928
0.594075
0.742329
0.853919
0.707144
0.822149
0.916377
0.911381
0.806024
0.714082
−0.13747
−0.111496
0.022672
−0.022252
0.07756
0.229297
0.119049
−0.010042
0.021655
0.153655
0.251796
0.220237
0.07572
0.206173
0.314294
0.158091
0.133719
0.262897
0.462776
0.528053
0.396857
0.4466 (15)
0.7166 (11)
0.7867 (15)
−0.0566 (14)
0.2351 (10)
0.2793 (15)
0.091158
0.276444
0.13601
0.362345
−0.12536
−0.231136
−0.154167
−0.086357
−0.12043
−0.284225
−0.49121
−0.53433
−0.372205
−0.038952
0.110254
0.255697
0.37658
0.494463
0.409801
0.354842
0.61581
0.746554
0.662869
0.444865
0.31336
−0.121146
−0.257602
−0.172967
−0.119636
−0.344647
−0.500341
−0.469753
−0.278421
−0.121396
0.103 (3)
0.228 (2)
0.015 (2)
0.115 (3)
0.217 (2)
0.011 (3)
0.0269*
0.02*
0.028*
0.028*
0.028*
0.0254*
0.033*
0.033*
0.145249
0.076649
0.496072
0.671138
0.672317
0.496343
0.320584
0.895182
1.010522
0.924411
0.252785
0.357345
0.344342
0.435372
0.157325
−0.039111
−0.202887
−0.167404
0.028844
0.319982
0.190041
0.16119
0.108701
0.426594
0.590967
0.683548
0.612603
0.447694
0.481 (2)
0.244 (3)
0.281 (3)
0.481 (3)
0.246 (3)
0.274 (3)
0.0327*
0.0282*
0.0295*
0.0338*
0.0392*
0.0214*
0.0303*
0.0303*
0.0303*
0.0312*
0.0333*
0.0325*
0.0321*
0.0262*
0.0257*
0.0438*
0.0438*
0.0438*
0.0323*
0.0404*
0.0401*
0.0358*
0.0286*
0.0187*
0.0182*
0.0193*
0.0204*
0.0187*
0.021*
H1n2a
H1n3a
H1n1b
H1n2b
H1n3b
2
Atomic displacement parameters (Å )
11
22
33
12
13
23
U
U
U
U
U
U
P1a
P1b
F1a
F2a
F1b
F2b
O1a
0.0123 (2)
0.0126 (2)
0.0372 (8)
0.0520 (10)
0.0331 (8)
0.0508 (10)
0.0147 (7)
0.0121 (2)
0.0130 (2)
0.0269 (7)
0.0373 (8)
0.0215 (6)
0.0352 (8)
0.0156 (7)
0.0137 (2)
0.00083 (16)
0.00084 (17)
−0.0001 (6)
−0.0070 (7)
0.0036 (5)
−0.00338 (18)
−0.00369 (18)
−0.0154 (6)
−0.0123 (7)
−0.0126 (5)
−0.0294 (7)
−0.0045 (6)
−0.00343 (17)
−0.00329 (17)
0.0032 (6)
−0.0156 (6)
−0.0070 (5)
−0.0157 (6)
−0.0053 (5)
0.0142 (2)
0.0317 (7)
0.0316 (8)
0.0225 (6)
0.0397 (8)
0.0189 (7)
0.0061 (7)
0.0006 (5)
Acta Cryst. (2018). C74
sup-12

supporting information
O2a
0.0150 (8)
0.0155 (7)
0.0155 (8)
0.0123 (9)
0.0124 (9)
0.0134 (9)
0.0115 (9)
0.0206 (7)
0.0160 (7)
0.0214 (8)
0.0147 (8)
0.0176 (8)
0.0203 (8)
0.0162 (8)
0.0200 (8)
0.0251 (9)
0.0160 (9)
0.0145 (10)
0.0180 (10)
0.0163 (12)
0.0127 (11)
0.0259 (13)
0.0231 (11)
0.0189 (10)
0.0202 (11)
0.0170 (10)
0.0271 (11)
0.0308 (13)
0.0241 (12)
0.0235 (11)
0.0205 (10)
0.0197 (10)
0.0169 (10)
0.0169 (10)
0.0216 (10)
0.0225 (11)
0.0227 (11)
0.0281 (11)
0.0229 (11)
0.0170 (10)
0.0153 (10)
0.0163 (10)
0.0167 (10)
0.0148 (10)
0.0239 (12)
0.0215 (11)
0.0214 (10)
0.0224 (11)
0.0232 (11)
0.0324 (12)
0.0342 (12)
0.0245 (11)
0.0210 (11)
0.0216 (10)
0.0300 (12)
0.0311 (8)
0.0205 (7)
0.0301 (8)
0.0208 (8)
0.0146 (8)
0.0157 (8)
0.0242 (8)
0.0145 (8)
0.0144 (8)
0.0157 (9)
0.0261 (11)
0.0337 (12)
0.0611 (18)
0.073 (2)
0.0505 (17)
0.0310 (12)
0.0162 (10)
0.0187 (10)
0.0159 (9)
0.0221 (10)
0.0250 (12)
0.0300 (12)
0.0340 (12)
0.0239 (11)
0.0154 (9)
0.0200 (10)
0.0178 (10)
0.0199 (10)
0.0284 (12)
0.0244 (11)
0.0182 (10)
0.0208 (10)
0.0169 (9)
0.0210 (10)
0.0187 (10)
0.0277 (11)
0.0355 (12)
0.0362 (13)
0.0266 (11)
0.0152 (9)
0.0218 (10)
0.0168 (10)
0.0180 (10)
0.0160 (10)
0.0251 (11)
0.0238 (11)
0.0173 (10)
0.0155 (10)
0.0015 (6)
0.0007 (5)
−0.0001 (6)
0.0016 (6)
0.0003 (6)
0.0024 (7)
0.0008 (7)
0.0018 (7)
0.0017 (7)
0.0005 (8)
−0.0016 (8)
−0.0011 (9)
0.0017 (10)
0.0004 (10)
−0.0107 (11)
−0.0069 (9)
0.0015 (8)
0.0051 (9)
−0.0007 (8)
−0.0008 (9)
−0.0021 (10)
−0.0001 (10)
0.0001 (9)
0.0001 (8)
0.0004 (8)
−0.0007 (9)
0.0039 (8)
−0.0005 (8)
−0.0042 (9)
0.0003 (9)
0.0015 (9)
−0.0008 (9)
0.0003 (8)
−0.0016 (8)
−0.0025 (8)
0.0014 (8)
0.0013 (9)
−0.0004 (10)
−0.0016 (9)
0.0030 (8)
0.0042 (9)
−0.0027 (8)
0.0021 (9)
−0.0052 (10)
−0.0062 (9)
0.0007 (9)
−0.0013 (8)
−0.0014 (9)
−0.0076 (6)
−0.0050 (6)
−0.0071 (6)
−0.0055 (7)
−0.0027 (7)
−0.0048 (7)
−0.0062 (7)
−0.0027 (7)
−0.0049 (7)
−0.0032 (8)
0.0008 (8)
−0.0025 (10)
−0.0012 (13)
0.0163 (14)
0.0131 (13)
0.0041 (10)
−0.0036 (8)
−0.0088 (9)
−0.0064 (8)
−0.0016 (9)
−0.0008 (10)
−0.0133 (11)
−0.0103 (10)
−0.0054 (9)
−0.0052 (8)
0.0003 (9)
−0.0045 (8)
−0.0055 (9)
−0.0055 (10)
−0.0035 (9)
−0.0072 (9)
−0.0085 (9)
−0.0044 (8)
−0.0034 (8)
−0.0033 (8)
−0.0058 (9)
−0.0024 (10)
−0.0082 (11)
−0.0108 (10)
−0.0028 (8)
−0.0100 (9)
−0.0060 (8)
−0.0011 (9)
−0.0030 (9)
−0.0110 (10)
−0.0062 (10)
−0.0037 (8)
−0.0064 (8)
−0.0082 (6)
−0.0047 (5)
−0.0060 (6)
−0.0047 (6)
−0.0026 (6)
−0.0055 (6)
−0.0047 (7)
−0.0045 (6)
−0.0047 (7)
−0.0022 (7)
−0.0059 (8)
0.0009 (9)
0.0042 (11)
−0.0083 (12)
−0.0226 (12)
−0.0096 (9)
−0.0042 (8)
−0.0074 (8)
−0.0046 (8)
−0.0016 (8)
0.0059 (9)
O1b
O2b
N1a
N2a
N3a
N1b
N2b
N3b
C1a
C2a
C3a
C4a
C5a
C6a
C7a
C8a
C9a
C10a
C11a
C12a
C13a
C14a
C15a
C16a
C17a
C18a
C19a
C20a
C21a
C22a
C23a
C1b
C2b
C3b
C4b
C5b
C6b
C7b
C8b
C9b
0.0122 (9)
0.0139 (9)
0.0167 (11)
0.0172 (11)
0.0219 (12)
0.0305 (15)
0.0372 (16)
0.0393 (16)
0.0271 (13)
0.0160 (11)
0.0404 (14)
0.0206 (11)
0.0238 (12)
0.0342 (15)
0.0369 (14)
0.0257 (13)
0.0205 (11)
0.0163 (11)
0.0303 (13)
0.0173 (11)
0.0221 (11)
0.0306 (13)
0.0296 (13)
0.0339 (13)
0.0279 (12)
0.0162 (11)
0.0165 (11)
0.0205 (11)
0.0262 (13)
0.0312 (14)
0.0413 (15)
0.0291 (13)
0.0174 (11)
0.0348 (14)
0.0147 (10)
0.0257 (12)
0.0297 (13)
0.0306 (13)
0.0350 (14)
0.0263 (12)
0.0211 (11)
0.0056 (9)
0.0020 (9)
0.0001 (8)
−0.0053 (8)
−0.0051 (8)
−0.0030 (8)
−0.0043 (8)
−0.0045 (9)
0.0034 (9)
−0.0011 (9)
−0.0036 (8)
−0.0037 (8)
−0.0040 (8)
−0.0035 (8)
0.0006 (8)
−0.0060 (9)
−0.0150 (10)
−0.0076 (9)
−0.0068 (8)
−0.0086 (8)
−0.0041 (8)
−0.0065 (9)
−0.0004 (9)
0.0025 (9)
C10b
C11b
C12b
C13b
C14b
C15b
C16b
−0.0053 (8)
−0.0052 (8)
−0.0071 (8)
Acta Cryst. (2018). C74
sup-13

supporting information
C17b
C18b
C19b
C20b
C21b
C22b
C23b
0.0572 (18)
0.0225 (12)
0.0393 (15)
0.0564 (18)
0.0483 (17)
0.0282 (13)
0.0249 (12)
0.0270 (12)
0.0200 (10)
0.0257 (11)
0.0265 (12)
0.0204 (11)
0.0240 (11)
0.0247 (11)
0.0246 (12)
0.0174 (10)
0.0202 (10)
0.0196 (11)
0.0224 (11)
0.0323 (12)
0.0194 (10)
−0.0130 (11)
0.0066 (8)
−0.0025 (11)
−0.0055 (8)
−0.0127 (10)
−0.0132 (11)
0.0021 (11)
−0.0036 (10)
−0.0067 (9)
−0.0104 (9)
−0.0070 (8)
−0.0094 (9)
−0.0054 (9)
0.0017 (9)
−0.0002 (9)
0.0017 (8)
0.0065 (10)
0.0109 (11)
0.0043 (10)
0.0013 (10)
0.0021 (9)
Geometric parameters (Å, º)
P1a—O1a
P1a—N1a
P1a—N2a
P1a—N3a
P1b—O1b
P1b—N1b
P1b—N2b
P1b—N3b
F1a—C3a
1.4808 (17)
C17a—H2c17a
C17a—H3c17a
C18a—C19a
C18a—C23a
C19a—C20a
C19a—H1c19a
C20a—C21a
C20a—H1c20a
C21a—C22a
C21a—H1c21a
C22a—C23a
C22a—H1c22a
C23a—H1c23a
C1b—C2b
C2b—C3b
C2b—C7b
C3b—C4b
C4b—C5b
C4b—H1c4b
C5b—C6b
C5b—H1c5b
C6b—C7b
C6b—H1c6b
C8b—C9b
C8b—C10b
C8b—H1c8b
C9b—H1c9b
C9b—H2c9b
C9b—H3c9b
C10b—C11b
C10b—C15b
C11b—C12b
C11b—H1c11b
C12b—C13b
C12b—H1c12b
C13b—C14b
C13b—H1c13b
C14b—C15b
0.9599
0.96
1.7081 (18)
1.6219 (19)
1.6199 (17)
1.4784 (17)
1.6986 (19)
1.618 (2)
1.6181 (17)
1.352 (3)
1.346 (3)
1.349 (3)
1.349 (3)
1.225 (3)
1.218 (3)
1.355 (3)
0.862 (18)
1.469 (2)
0.859 (12)
1.463 (3)
0.861 (19)
1.367 (3)
0.865 (16)
1.459 (3)
0.856 (10)
1.460 (3)
0.861 (17)
1.498 (3)
1.389 (3)
1.396 (4)
1.378 (3)
1.370 (5)
0.9601
1.396 (3)
1.398 (3)
1.391 (3)
0.9599
1.380 (4)
0.9599
1.395 (4)
0.96
1.382 (3)
0.9601
F2a—C7a
F1b—C3b
F2b—C7b
O2a—C1a
O2b—C1b
N1a—C1a
N1a—H1n1a
N2a—C8a
N2a—H1n2a
N3a—C16a
N3a—H1n3a
N1b—C1b
N1b—H1n1b
N2b—C8b
N2b—H1n2b
N3b—C16b
N3b—H1n3b
C1a—C2a
C2a—C3a
C2a—C7a
C3a—C4a
C4a—C5a
C4a—H1c4a
C5a—C6a
C5a—H1c5a
C6a—C7a
C6a—H1c6a
C8a—C9a
C8a—C10a
0.9601
1.505 (3)
1.390 (3)
1.392 (4)
1.375 (3)
1.383 (4)
0.9601
1.386 (4)
0.96
1.383 (3)
0.9599
1.534 (3)
1.523 (3)
0.9601
0.96
0.9599
0.96
1.395 (3)
1.393 (3)
1.384 (3)
0.96
1.382 (4)
0.96
1.388 (3)
0.96
1.385 (3)
1.393 (5)
0.96
1.377 (4)
0.9599
1.531 (3)
1.525 (3)
Acta Cryst. (2018). C74
sup-14

supporting information
C8a—H1c8a
C9a—H1c9a
C9a—H2c9a
C9a—H3c9a
C10a—C11a
C10a—C15a
C11a—C12a
C11a—H1c11a
C12a—C13a
C12a—H1c12a
C13a—C14a
C13a—H1c13a
C14a—C15a
C14a—H1c14a
C15a—H1c15a
C16a—C17a
C16a—C18a
C16a—H1c16a
C17a—H1c17a
0.9601
0.96
0.9599
0.96
C14b—H1c14b
C15b—H1c15b
C16b—C17b
0.96
0.96
1.528 (4)
1.521 (3)
0.9601
0.9601
0.9599
0.9601
1.392 (3)
1.383 (4)
1.381 (3)
0.9601
1.385 (4)
0.9601
1.389 (4)
0.96
C16b—C18b
1.397 (3)
1.385 (3)
1.384 (3)
0.9601
1.384 (4)
0.9601
1.385 (3)
0.96
1.390 (3)
0.9599
0.9599
1.530 (3)
1.526 (2)
0.9601
0.9601
C16b—H1c16b
C17b—H1c17b
C17b—H2c17b
C17b—H3c17b
C18b—C19b
C18b—C23b
C19b—C20b
C19b—H1c19b
C20b—C21b
C20b—H1c20b
C21b—C22b
C21b—H1c21b
C22b—C23b
C22b—H1c22b
C23b—H1c23b
1.395 (3)
0.9599
0.9599
O1a—P1a—N1a
O1a—P1a—N2a
O1a—P1a—N3a
N1a—P1a—N2a
N1a—P1a—N3a
N2a—P1a—N3a
O1b—P1b—N1b
O1b—P1b—N2b
O1b—P1b—N3b
N1b—P1b—N2b
N1b—P1b—N3b
N2b—P1b—N3b
P1a—N1a—C1a
P1a—N1a—H1n1a
C1a—N1a—H1n1a
P1a—N2a—C8a
P1a—N2a—H1n2a
C8a—N2a—H1n2a
P1a—N3a—C16a
P1a—N3a—H1n3a
C16a—N3a—H1n3a
P1b—N1b—C1b
P1b—N1b—H1n1b
C1b—N1b—H1n1b
P1b—N2b—C8b
P1b—N2b—H1n2b
C8b—N2b—H1n2b
P1b—N3b—C16b
103.29 (9)
115.49 (8)
115.08 (10)
109.87 (10)
109.77 (8)
103.37 (9)
102.89 (9)
116.28 (8)
116.30 (10)
109.74 (10)
109.71 (9)
101.94 (10)
123.03 (15)
118.7 (18)
118.3 (18)
122.96 (14)
114.9 (17)
116.2 (18)
123.75 (16)
116.7 (17)
119.4 (18)
125.57 (16)
118.1 (18)
116.3 (18)
124.36 (15)
116.7 (17)
115.1 (18)
123.82 (16)
C18a—C19a—C20a
120.2 (2)
119.9
119.91
121.1 (2)
119.45
119.45
119.1 (2)
120.44
120.43
120.0 (2)
120.01
C18a—C19a—H1c19a
C20a—C19a—H1c19a
C19a—C20a—C21a
C19a—C20a—H1c20a
C21a—C20a—H1c20a
C20a—C21a—C22a
C20a—C21a—H1c21a
C22a—C21a—H1c21a
C21a—C22a—C23a
C21a—C22a—H1c22a
C23a—C22a—H1c22a
C18a—C23a—C22a
C18a—C23a—H1c23a
C22a—C23a—H1c23a
O2b—C1b—N1b
O2b—C1b—C2b
N1b—C1b—C2b
C1b—C2b—C3b
C1b—C2b—C7b
C3b—C2b—C7b
F1b—C3b—C2b
F1b—C3b—C4b
C2b—C3b—C4b
120
121.4 (2)
119.33
119.32
123.66 (19)
121.8 (2)
114.51 (19)
123.3 (2)
121.3 (2)
115.4 (2)
118.00 (19)
118.5 (2)
123.5 (2)
118.9 (2)
120.55
C3b—C4b—C5b
C3b—C4b—H1c4b
C5b—C4b—H1c4b
C4b—C5b—C6b
120.55
120.3 (2)
Acta Cryst. (2018). C74
sup-15

supporting information
P1b—N3b—H1n3b
C16b—N3b—H1n3b
O2a—C1a—N1a
O2a—C1a—C2a
N1a—C1a—C2a
C1a—C2a—C3a
C1a—C2a—C7a
C3a—C2a—C7a
F1a—C3a—C2a
117.7 (19)
118.4 (18)
122.3 (2)
120.9 (2)
116.76 (19)
123.5 (2)
120.6 (2)
115.8 (2)
118.0 (2)
119.0 (2)
122.9 (3)
119.1 (3)
120.45
120.46
120.8 (2)
119.58
119.59
118.2 (3)
120.88
C4b—C5b—H1c5b
C6b—C5b—H1c5b
C5b—C6b—C7b
C5b—C6b—H1c6b
C7b—C6b—H1c6b
F2b—C7b—C2b
F2b—C7b—C6b
C2b—C7b—C6b
N2b—C8b—C9b
119.82
119.83
118.6 (3)
120.69
120.7
118.1 (2)
118.7 (2)
123.2 (2)
111.10 (16)
110.97 (17)
107.94
111.28 (19)
107.62
107.75
109.47
109.47
109.47
109.48
109.47
109.48
119.68 (19)
122.50 (17)
117.82 (19)
121.1 (2)
119.44
119.44
120.6 (2)
119.67
119.68
118.8 (2)
120.61
120.61
120.7 (2)
119.66
119.66
120.92 (19)
119.54
119.54
108.99 (18)
113.5 (2)
107.25
110.12 (17)
110.84
106.06
109.47
109.47
109.47
F1a—C3a—C4a
C2a—C3a—C4a
C3a—C4a—C5a
N2b—C8b—C10b
N2b—C8b—H1c8b
C9b—C8b—C10b
C9b—C8b—H1c8b
C10b—C8b—H1c8b
C8b—C9b—H1c9b
C8b—C9b—H2c9b
C8b—C9b—H3c9b
H1c9b—C9b—H2c9b
H1c9b—C9b—H3c9b
H2c9b—C9b—H3c9b
C8b—C10b—C11b
C8b—C10b—C15b
C11b—C10b—C15b
C10b—C11b—C12b
C10b—C11b—H1c11b
C12b—C11b—H1c11b
C11b—C12b—C13b
C11b—C12b—H1c12b
C13b—C12b—H1c12b
C12b—C13b—C14b
C12b—C13b—H1c13b
C14b—C13b—H1c13b
C13b—C14b—C15b
C13b—C14b—H1c14b
C15b—C14b—H1c14b
C10b—C15b—C14b
C10b—C15b—H1c15b
C14b—C15b—H1c15b
N3b—C16b—C17b
C3a—C4a—H1c4a
C5a—C4a—H1c4a
C4a—C5a—C6a
C4a—C5a—H1c5a
C6a—C5a—H1c5a
C5a—C6a—C7a
C5a—C6a—H1c6a
C7a—C6a—H1c6a
F2a—C7a—C2a
120.88
118.2 (2)
118.7 (3)
123.1 (3)
112.49 (16)
111.31 (16)
106.17
109.74 (18)
107.86
109.12
109.47
109.47
109.47
109.48
F2a—C7a—C6a
C2a—C7a—C6a
N2a—C8a—C9a
N2a—C8a—C10a
N2a—C8a—H1c8a
C9a—C8a—C10a
C9a—C8a—H1c8a
C10a—C8a—H1c8a
C8a—C9a—H1c9a
C8a—C9a—H2c9a
C8a—C9a—H3c9a
H1c9a—C9a—H2c9a
H1c9a—C9a—H3c9a
H2c9a—C9a—H3c9a
C8a—C10a—C11a
C8a—C10a—C15a
C11a—C10a—C15a
C10a—C11a—C12a
C10a—C11a—H1c11a
C12a—C11a—H1c11a
C11a—C12a—C13a
C11a—C12a—H1c12a
C13a—C12a—H1c12a
C12a—C13a—C14a
C12a—C13a—H1c13a
C14a—C13a—H1c13a
C13a—C14a—C15a
109.47
109.48
118.23 (19)
122.90 (16)
118.77 (19)
120.5 (2)
119.75
119.75
120.4 (2)
119.79
119.8
119.4 (2)
120.29
120.3
120.3 (2)
N3b—C16b—C18b
N3b—C16b—H1c16b
C17b—C16b—C18b
C17b—C16b—H1c16b
C18b—C16b—H1c16b
C16b—C17b—H1c17b
C16b—C17b—H2c17b
C16b—C17b—H3c17b
H1c17b—C17b—H2c17b
109.48
Acta Cryst. (2018). C74
sup-16

supporting information
C13a—C14a—H1c14a
C15a—C14a—H1c14a
C10a—C15a—C14a
C10a—C15a—H1c15a
C14a—C15a—H1c15a
N3a—C16a—C17a
119.85
119.85
120.59 (18)
119.7
119.71
109.06 (17)
113.06 (18)
108.25
112.13 (16)
109.25
104.91
109.47
109.47
109.47
109.47
109.46
109.48
H1c17b—C17b—H3c17b
109.46
109.47
H2c17b—C17b—H3c17b
C16b—C18b—C19b
C16b—C18b—C23b
C19b—C18b—C23b
C18b—C19b—C20b
C18b—C19b—H1c19b
C20b—C19b—H1c19b
C19b—C20b—C21b
C19b—C20b—H1c20b
C21b—C20b—H1c20b
C20b—C21b—C22b
C20b—C21b—H1c21b
C22b—C21b—H1c21b
C21b—C22b—C23b
C21b—C22b—H1c22b
C23b—C22b—H1c22b
C18b—C23b—C22b
C18b—C23b—H1c23b
C22b—C23b—H1c23b
118.2 (2)
123.1 (2)
118.69 (19)
120.9 (3)
119.53
119.53
120.4 (2)
119.8
119.81
119.2 (2)
120.42
120.43
120.2 (3)
119.88
N3a—C16a—C18a
N3a—C16a—H1c16a
C17a—C16a—C18a
C17a—C16a—H1c16a
C18a—C16a—H1c16a
C16a—C17a—H1c17a
C16a—C17a—H2c17a
C16a—C17a—H3c17a
H1c17a—C17a—H2c17a
H1c17a—C17a—H3c17a
H2c17a—C17a—H3c17a
C16a—C18a—C19a
C16a—C18a—C23a
C19a—C18a—C23a
119.88
120.5 (2)
119.72
122.2 (2)
119.5 (2)
118.25 (18)
119.74
P1a—N2a—C8a—C9a
P1b—N2b—C8b—C9b
P1a—N3a—C16a—C17a
P1b—N3b—C16b—C17b
O1a—P1a—N1a—C1a
O1b—P1b—N1b—C1b
O1a—P1a—N2a—C8a
O1b—P1b—N2b—C8b
−88.5 (2)
O1a—P1a—N3a—C16a
O1b—P1b—N3b—C16b
P1a—N1a—C1a—O2a
P1b—N1b—C1b—O2b
P1a—N2a—C8a—C10a
P1b—N2b—C8b—C10b
P1a—N3a—C16a—C18a
P1b—N3b—C16b—C18b
25.1 (2)
42.1 (2)
1.4 (3)
−1.2 (3)
147.93 (15)
134.66 (16)
116.90 (18)
115.40 (19)
−101.0 (2)
−117.68 (19)
−121.47 (19)
177.16 (16)
178.46 (17)
−51.78 (19)
−55.44 (19)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
i
C5a—H1c5a···O1a
0.96
2.34
3.271 (3)
2.863 (2)
2.907 (2)
2.938 (3)
2.812 (2)
2.858 (2)
2.887 (3)
162.23
173 (3)
154 (3)
155 (2)
173 (2)
158 (3)
157 (2)
N1a—H1n1a···O2b
N2a—H1n2a···O1b
0.862 (18)
0.859 (12)
0.861 (19)
0.865 (16)
0.856 (10)
0.861 (17)
2.006 (16)
2.110 (12)
2.13 (2)
1.951 (14)
2.046 (13)
2.07 (2)
ii
ii
N3a—H1n3a···O1b
N1b—H1n1b···O2a
iii
N2b—H1n2b···O1a
N3b—H1n3b···O1a
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x−1, y, z.
Acta Cryst. (2018). C74
sup-17