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

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 R₂²(10), R₂¹(6) and C₂²(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.

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: JANA2006 (Version 24/09/2015; Petříček et al., 2014); program(s) used to refine structure: JANA2006 (Version 24/09/2015; Petříček et al., 2014); 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

C23H24F2N3O2P	Z = 2
Mr = 443.4	F(000) = 464
Triclinic, P1	Dx = 1.334 Mg m^−3
Hall symbol: P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.7608 (3) Å	Cell parameters from 14044 reflections
b = 10.6134 (3) Å	θ = 4.1–67.2°
c = 11.2721 (3) Å	µ = 1.47 mm^−1
α = 77.398 (2)°	T = 120 K
β = 75.589 (2)°	Prism, colourless
γ = 87.635 (2)°	0.53 × 0.19 × 0.08 mm
V = 1103.64 (6) Å^3

Data collection

Agilent Xcalibur/Gemini ultra diffractometer with an AtlasS2 detector	7492 independent reflections
Radiation source: X-ray tube	6976 reflections with I > 3σ(I)
Mirror monochromator	Rint = 0.051
Detector resolution: 5.1783 pixels mm^-1	θmax = 67.2°, θmin = 4.2°
ω scans	h = −11→11
Absorption correction: analytical (CrysAlis PRO; Rigaku OD, 2015)	k = −12→12
Tmin = 0.562, Tmax = 0.896	l = −13→13
21163 measured reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F > 3σ(F)] = 0.047	Weighting scheme based on measured s.u.'s w = 1/(σ^2(I) + 0.0016I^2)
wR(F) = 0.121	(Δ/σ)max = 0.038
S = 1.71	Δρmax = 0.30 e Å^−3
7492 reflections	Δρmin = −0.31 e Å^−3
578 parameters	Absolute structure: 3546 of Friedel pairs used in the refinement
6 restraints	Absolute structure parameter: 0.014 (17)
177 constraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1a	0.42969 (8)	0.70347 (7)	0.88573 (6)	0.01478 (19)
P1b	0.93005 (8)	0.70016 (7)	0.87843 (6)	0.0155 (2)
F1a	0.5086 (2)	0.30564 (19)	1.06091 (18)	0.0402 (7)
F2a	0.3523 (2)	0.3273 (2)	0.69523 (18)	0.0480 (8)
F1b	1.0313 (2)	0.32193 (17)	1.06766 (15)	0.0316 (6)
F2b	0.8561 (3)	0.2938 (2)	0.7220 (2)	0.0472 (8)
O1a	0.56352 (19)	0.76047 (18)	0.89095 (16)	0.0186 (6)
O2a	0.2576 (2)	0.4860 (2)	0.8713 (2)	0.0267 (7)
O1b	1.0676 (2)	0.75981 (18)	0.86840 (17)	0.0199 (6)
O2b	0.7535 (2)	0.4649 (2)	0.8922 (2)	0.0270 (7)
N1a	0.4696 (2)	0.5453 (2)	0.8883 (2)	0.0193 (7)
N2a	0.3729 (2)	0.7653 (2)	0.7623 (2)	0.0182 (7)
N3a	0.2950 (2)	0.7135 (2)	1.0014 (2)	0.0191 (7)
N1b	0.9696 (3)	0.5418 (2)	0.8846 (2)	0.0215 (8)
N2b	0.8565 (2)	0.7539 (2)	0.7637 (2)	0.0195 (7)
N3b	0.8044 (2)	0.7135 (2)	0.9995 (2)	0.0215 (8)
C1a	0.3791 (3)	0.4570 (3)	0.8789 (2)	0.0192 (8)
C2a	0.4316 (3)	0.3239 (3)	0.8761 (3)	0.0237 (9)
C3a	0.4958 (3)	0.2516 (3)	0.9652 (3)	0.0323 (10)
C4a	0.5419 (4)	0.1282 (3)	0.9637 (4)	0.0504 (15)
C5a	0.5248 (4)	0.0723 (4)	0.8694 (4)	0.0557 (16)
C6a	0.4603 (4)	0.1387 (4)	0.7779 (4)	0.0511 (15)
C7a	0.4152 (4)	0.2616 (3)	0.7837 (3)	0.0342 (11)
C8a	0.4603 (3)	0.7797 (3)	0.6343 (2)	0.0205 (9)
C9a	0.4546 (4)	0.6600 (3)	0.5804 (3)	0.0327 (11)
C10a	0.4202 (3)	0.8990 (3)	0.5472 (2)	0.0213 (9)
C11a	0.5229 (3)	0.9569 (3)	0.4419 (3)	0.0322 (10)
C12a	0.4906 (4)	1.0599 (4)	0.3554 (3)	0.0416 (12)
C13a	0.3523 (4)	1.1058 (3)	0.3731 (3)	0.0396 (12)
C14a	0.2513 (4)	1.0499 (3)	0.4773 (3)	0.0360 (11)
C15a	0.2839 (3)	0.9467 (3)	0.5650 (3)	0.0282 (10)
C16a	0.3078 (3)	0.7245 (3)	1.1250 (2)	0.0203 (9)
C17a	0.2456 (3)	0.8532 (3)	1.1517 (3)	0.0293 (10)
C18a	0.2412 (3)	0.6102 (3)	1.2291 (2)	0.0203 (9)
C19a	0.1802 (3)	0.5051 (3)	1.2045 (3)	0.0271 (10)
C20a	0.1256 (4)	0.4021 (3)	1.3009 (3)	0.0343 (11)
C21a	0.1295 (4)	0.4001 (3)	1.4229 (3)	0.0341 (11)
C22a	0.1914 (4)	0.5041 (3)	1.4479 (3)	0.0347 (11)
C23a	0.2457 (3)	0.6075 (3)	1.3525 (3)	0.0300 (10)
C1b	0.8781 (3)	0.4461 (3)	0.8914 (2)	0.0197 (9)
C2b	0.9415 (3)	0.3151 (3)	0.8940 (3)	0.0217 (9)
C3b	1.0192 (3)	0.2573 (3)	0.9789 (2)	0.0225 (9)
C4b	1.0823 (3)	0.1402 (3)	0.9798 (3)	0.0304 (10)
C5b	1.0669 (4)	0.0719 (3)	0.8914 (3)	0.0356 (11)
C6b	0.9891 (4)	0.1230 (3)	0.8053 (3)	0.0419 (13)
C7b	0.9289 (3)	0.2418 (3)	0.8085 (3)	0.0299 (10)
C8b	0.9219 (3)	0.7565 (3)	0.6330 (2)	0.0216 (9)
C9b	0.8700 (3)	0.6444 (3)	0.5896 (3)	0.0299 (10)
C10b	0.8997 (3)	0.8862 (3)	0.5501 (2)	0.0210 (9)
C11b	0.9569 (3)	0.9079 (3)	0.4211 (3)	0.0327 (10)
C12b	0.9377 (3)	1.0240 (3)	0.3432 (3)	0.0342 (11)
C13b	0.8602 (4)	1.1209 (3)	0.3922 (3)	0.0339 (11)
C14b	0.8035 (4)	1.1001 (3)	0.5201 (3)	0.0326 (11)
C15b	0.8221 (3)	0.9846 (3)	0.5983 (2)	0.0272 (9)
C16b	0.8251 (3)	0.6982 (3)	1.1256 (2)	0.0254 (10)
C17b	0.7811 (5)	0.8217 (3)	1.1726 (3)	0.0446 (13)
C18b	0.7456 (3)	0.5832 (3)	1.2179 (2)	0.0233 (9)
C19b	0.7849 (4)	0.5382 (3)	1.3303 (3)	0.0341 (11)
C20b	0.7097 (4)	0.4404 (3)	1.4222 (3)	0.0421 (13)
C21b	0.5930 (4)	0.3847 (3)	1.4044 (3)	0.0406 (12)
C22b	0.5550 (4)	0.4259 (3)	1.2908 (3)	0.0370 (11)
C23b	0.6310 (3)	0.5237 (3)	1.1992 (3)	0.0281 (10)
H1n1a	0.5517 (16)	0.519 (3)	0.897 (3)	0.0232*
H1n2a	0.2832 (7)	0.754 (3)	0.775 (3)	0.0219*
H1n3a	0.2156 (17)	0.725 (3)	0.981 (3)	0.0229*
H1n1b	1.0552 (13)	0.521 (3)	0.887 (3)	0.0258*
H1n2b	0.7657 (3)	0.752 (3)	0.788 (3)	0.0234*
H1n3b	0.7227 (16)	0.727 (3)	0.984 (3)	0.0258*
H1c4a	0.585472	0.081706	1.027517	0.0605*
H1c5a	0.557726	−0.013751	0.866686	0.0668*
H1c6a	0.447712	0.099488	0.712181	0.0613*
H1c8a	0.555862	0.790094	0.639283	0.0246*
H1c9a	0.509728	0.67571	0.49513	0.0392*
H2c9a	0.492292	0.58757	0.629251	0.0392*
H3c9a	0.358272	0.641667	0.583119	0.0392*
H1c11a	0.617653	0.924764	0.429132	0.0387*
H1c12a	0.562681	1.099817	0.283514	0.05*
H1c13a	0.328311	1.176165	0.312557	0.0475*
H1c14a	0.156687	1.082278	0.489927	0.0432*
H1c15a	0.212086	0.908615	0.637905	0.0338*
H1c16a	0.406511	0.72268	1.1241	0.0243*
H1c17a	0.255892	0.862125	1.231992	0.0352*
H2c17a	0.294717	0.922963	1.087811	0.0352*
H3c17a	0.147048	0.855228	1.152057	0.0352*
H1c19a	0.176156	0.504521	1.120374	0.0326*
H1c20a	0.083993	0.33035	1.282784	0.0412*
H1c21a	0.090281	0.328179	1.489352	0.0409*
H1c22a	0.196098	0.503706	1.532064	0.0416*
H1c23a	0.287364	0.67901	1.371072	0.036*
H1c4b	1.136127	0.105687	1.039828	0.0365*
H1c5b	1.11031	−0.010774	0.890171	0.0427*
H1c6b	0.977386	0.076233	0.744438	0.0503*
H1c8b	1.021704	0.746021	0.624882	0.0259*
H1c9b	0.922789	0.643642	0.505619	0.0358*
H2c9b	0.883182	0.564432	0.644478	0.0358*
H3c9b	0.771347	0.654769	0.591375	0.0358*
H1c11b	1.010646	0.841365	0.385657	0.0392*
H1c12b	0.978358	1.037267	0.254574	0.0411*
H1c13b	0.846	1.201279	0.338293	0.0407*
H1c14b	0.750284	1.167145	0.555186	0.0392*
H1c15b	0.781179	0.971916	0.686835	0.0326*
H1c16b	0.923797	0.682112	1.120119	0.0304*
H1c17b	0.791586	0.811117	1.256696	0.0535*
H2c17b	0.839945	0.892379	1.119104	0.0535*
H3c17b	0.684089	0.839455	1.171712	0.0535*
H1c19b	0.865845	0.575859	1.344067	0.041*
H1c20b	0.738611	0.410967	1.498953	0.0505*
H1c21b	0.538781	0.318605	1.469283	0.0488*
H1c22b	0.475878	0.386164	1.276321	0.0444*
H1c23b	0.604158	0.550906	1.121233	0.0337*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1a	0.0129 (3)	0.0149 (3)	0.0189 (3)	0.0016 (2)	−0.0083 (2)	−0.0036 (2)
P1b	0.0137 (3)	0.0164 (3)	0.0191 (3)	0.0015 (2)	−0.0091 (2)	−0.0035 (2)
F1a	0.0465 (11)	0.0335 (11)	0.0442 (10)	0.0007 (9)	−0.0264 (9)	0.0017 (8)
F2a	0.0647 (14)	0.0466 (13)	0.0428 (11)	−0.0048 (11)	−0.0213 (10)	−0.0211 (9)
F1b	0.0435 (11)	0.0275 (9)	0.0320 (8)	0.0067 (8)	−0.0226 (8)	−0.0098 (7)
F2b	0.0636 (14)	0.0430 (12)	0.0550 (12)	0.0098 (11)	−0.0432 (11)	−0.0212 (9)
O1a	0.0158 (9)	0.0164 (9)	0.0261 (9)	0.0022 (7)	−0.0101 (7)	−0.0045 (7)
O2a	0.0179 (10)	0.0259 (11)	0.0418 (11)	0.0039 (8)	−0.0150 (8)	−0.0109 (9)
O1b	0.0160 (9)	0.0195 (10)	0.0274 (9)	0.0010 (8)	−0.0112 (7)	−0.0051 (7)
O2b	0.0183 (10)	0.0243 (11)	0.0417 (11)	0.0014 (9)	−0.0143 (8)	−0.0064 (8)
N1a	0.0166 (11)	0.0168 (12)	0.0275 (11)	0.0010 (9)	−0.0120 (9)	−0.0037 (9)
N2a	0.0146 (11)	0.0214 (12)	0.0214 (10)	0.0017 (9)	−0.0102 (9)	−0.0040 (9)
N3a	0.0116 (10)	0.0260 (13)	0.0230 (11)	0.0045 (9)	−0.0097 (8)	−0.0069 (9)
N1b	0.0160 (11)	0.0188 (12)	0.0326 (11)	0.0001 (10)	−0.0135 (10)	−0.0034 (9)
N2b	0.0165 (11)	0.0225 (12)	0.0229 (11)	0.0035 (10)	−0.0117 (9)	−0.0048 (9)
N3b	0.0158 (11)	0.0308 (13)	0.0210 (11)	0.0050 (10)	−0.0109 (9)	−0.0060 (9)
C1a	0.0167 (13)	0.0175 (14)	0.0245 (12)	0.0 (11)	−0.0072 (10)	−0.0046 (10)
C2a	0.0191 (13)	0.0165 (14)	0.0345 (14)	−0.0002 (11)	−0.0039 (11)	−0.0066 (11)
C3a	0.0245 (15)	0.0210 (15)	0.0460 (17)	0.0011 (13)	−0.0072 (13)	0.0025 (12)
C4a	0.039 (2)	0.0206 (18)	0.081 (3)	0.0037 (16)	−0.0086 (19)	0.0048 (17)
C5a	0.041 (2)	0.0179 (18)	0.090 (3)	0.0035 (16)	0.013 (2)	−0.0085 (19)
C6a	0.051 (2)	0.031 (2)	0.068 (3)	−0.0104 (18)	0.0102 (19)	−0.0286 (18)
C7a	0.0332 (17)	0.0282 (17)	0.0401 (17)	−0.0043 (14)	0.0001 (14)	−0.0144 (13)
C8a	0.0207 (14)	0.0213 (14)	0.0221 (12)	0.0034 (11)	−0.0103 (11)	−0.0051 (10)
C9a	0.054 (2)	0.0222 (16)	0.0268 (13)	0.0086 (14)	−0.0164 (13)	−0.0086 (11)
C10a	0.0232 (14)	0.0221 (14)	0.0225 (12)	0.0010 (12)	−0.0106 (11)	−0.0072 (10)
C11a	0.0301 (16)	0.0335 (17)	0.0317 (14)	0.0011 (13)	−0.0088 (12)	−0.0029 (12)
C12a	0.041 (2)	0.040 (2)	0.0334 (16)	−0.0029 (16)	−0.0046 (14)	0.0085 (14)
C13a	0.047 (2)	0.0285 (19)	0.0431 (17)	0.0028 (16)	−0.0236 (15)	0.0077 (13)
C14a	0.0298 (17)	0.0281 (18)	0.0485 (18)	0.0025 (14)	−0.0182 (14)	0.0043 (13)
C15a	0.0249 (15)	0.0250 (16)	0.0330 (14)	−0.0011 (12)	−0.0118 (12)	0.0027 (11)
C16a	0.0211 (13)	0.0244 (15)	0.0186 (12)	0.0003 (11)	−0.0104 (10)	−0.0052 (10)
C17a	0.0379 (17)	0.0236 (15)	0.0245 (13)	0.0002 (13)	−0.0032 (12)	−0.0063 (11)
C18a	0.0171 (13)	0.0216 (15)	0.0233 (12)	0.0063 (11)	−0.0086 (10)	−0.0038 (10)
C19a	0.0315 (16)	0.0251 (15)	0.0290 (14)	−0.0003 (13)	−0.0143 (12)	−0.0064 (11)
C20a	0.0391 (18)	0.0276 (17)	0.0377 (16)	−0.0031 (14)	−0.0128 (14)	−0.0056 (12)
C21a	0.0367 (17)	0.0285 (17)	0.0314 (15)	0.0005 (14)	−0.0084 (13)	0.0056 (12)
C22a	0.0404 (18)	0.0393 (19)	0.0239 (14)	0.0029 (15)	−0.0115 (12)	−0.0020 (12)
C23a	0.0357 (16)	0.0324 (17)	0.0251 (13)	0.0010 (13)	−0.0140 (12)	−0.0059 (11)
C1b	0.0175 (14)	0.0190 (14)	0.0242 (12)	0.0005 (11)	−0.0089 (10)	−0.0040 (10)
C2b	0.0200 (13)	0.0197 (15)	0.0280 (13)	−0.0005 (12)	−0.0094 (11)	−0.0061 (11)
C3b	0.0229 (14)	0.0209 (14)	0.0248 (12)	−0.0009 (11)	−0.0075 (11)	−0.0055 (10)
C4b	0.0306 (16)	0.0226 (16)	0.0364 (15)	0.0032 (13)	−0.0108 (13)	−0.0005 (12)
C5b	0.0396 (19)	0.0195 (16)	0.0459 (17)	0.0050 (14)	−0.0052 (15)	−0.0102 (13)
C6b	0.054 (2)	0.0312 (19)	0.0495 (19)	0.0010 (16)	−0.0182 (17)	−0.0208 (15)
C7b	0.0342 (17)	0.0259 (16)	0.0372 (15)	0.0013 (13)	−0.0187 (13)	−0.0117 (12)
C8b	0.0210 (13)	0.0253 (15)	0.0233 (12)	0.0048 (11)	−0.0117 (11)	−0.0092 (11)
C9b	0.0394 (17)	0.0260 (16)	0.0302 (14)	0.0045 (13)	−0.0166 (12)	−0.0103 (11)
C10b	0.0174 (13)	0.0271 (15)	0.0218 (12)	−0.0012 (11)	−0.0106 (10)	−0.0053 (11)
C11b	0.0314 (16)	0.0410 (18)	0.0248 (13)	0.0023 (14)	−0.0052 (12)	−0.0074 (12)
C12b	0.0359 (17)	0.0410 (19)	0.0222 (13)	−0.0049 (15)	−0.0067 (12)	0.0014 (12)
C13b	0.0395 (18)	0.0302 (17)	0.0328 (15)	−0.0074 (14)	−0.0192 (13)	0.0052 (12)
C14b	0.0416 (18)	0.0256 (16)	0.0328 (15)	0.0020 (14)	−0.0135 (13)	−0.0059 (12)
C15b	0.0317 (15)	0.0294 (16)	0.0220 (13)	−0.0006 (13)	−0.0094 (11)	−0.0054 (11)
C16b	0.0237 (14)	0.0383 (18)	0.0186 (12)	−0.0012 (13)	−0.0109 (11)	−0.0088 (11)
C17b	0.068 (3)	0.0351 (19)	0.0310 (16)	−0.0144 (18)	−0.0050 (16)	−0.0126 (13)
C18b	0.0238 (14)	0.0268 (16)	0.0217 (12)	0.0080 (12)	−0.0088 (11)	−0.0084 (11)
C19b	0.049 (2)	0.0337 (18)	0.0271 (14)	0.0092 (15)	−0.0220 (14)	−0.0099 (12)
C20b	0.072 (3)	0.0321 (19)	0.0264 (15)	0.0147 (18)	−0.0222 (16)	−0.0063 (13)
C21b	0.058 (2)	0.0265 (17)	0.0296 (15)	0.0093 (16)	−0.0053 (15)	0.0021 (12)
C22b	0.0350 (17)	0.0312 (18)	0.0418 (16)	0.0007 (15)	−0.0097 (14)	−0.0014 (14)
C23b	0.0264 (15)	0.0307 (17)	0.0286 (14)	0.0043 (13)	−0.0135 (12)	−0.0021 (12)

Geometric parameters (Å, º)

P1a—O1a	1.481 (2)	C17a—H2c17a	0.96
P1a—N1a	1.703 (2)	C17a—H3c17a	0.96
P1a—N2a	1.621 (2)	C18a—C19a	1.396 (5)
P1a—N3a	1.624 (2)	C18a—C23a	1.397 (4)
P1b—O1b	1.477 (2)	C19a—C20a	1.378 (4)
P1b—N1b	1.699 (3)	C19a—H1c19a	0.96
P1b—N2b	1.619 (3)	C20a—C21a	1.381 (5)
P1b—N3b	1.620 (2)	C20a—H1c20a	0.9599
F1a—C3a	1.361 (5)	C21a—C22a	1.393 (5)
F2a—C7a	1.351 (4)	C21a—H1c21a	0.96
F1b—C3b	1.359 (4)	C22a—C23a	1.375 (4)
F2b—C7b	1.355 (4)	C22a—H1c22a	0.96
O2a—C1a	1.232 (3)	C23a—H1c23a	0.9601
O2b—C1b	1.223 (3)	C1b—C2b	1.495 (4)
N1a—C1a	1.351 (4)	C2b—C3b	1.391 (4)
N1a—H1n1a	0.86 (2)	C2b—C7b	1.395 (5)
N2a—C8a	1.461 (3)	C3b—C4b	1.363 (4)
N2a—H1n2a	0.860 (9)	C4b—C5b	1.393 (5)
N3a—C16a	1.459 (4)	C4b—H1c4b	0.96
N3a—H1n3a	0.86 (2)	C5b—C6b	1.385 (6)
N1b—C1b	1.358 (4)	C5b—H1c5b	0.96
N1b—H1n1b	0.860 (17)	C6b—C7b	1.373 (5)
N2b—C8b	1.447 (3)	C6b—H1c6b	0.96
N2b—H1n2b	0.860 (14)	C8b—C9b	1.529 (5)
N3b—C16b	1.458 (4)	C8b—C10b	1.526 (4)
N3b—H1n3b	0.86 (2)	C8b—H1c8b	0.96
C1a—C2a	1.487 (4)	C9b—H1c9b	0.96
C2a—C3a	1.389 (5)	C9b—H2c9b	0.96
C2a—C7a	1.392 (5)	C9b—H3c9b	0.96
C3a—C4a	1.369 (5)	C10b—C11b	1.393 (4)
C4a—C5a	1.372 (7)	C10b—C15b	1.392 (4)
C4a—H1c4a	0.96	C11b—C12b	1.384 (4)
C5a—C6a	1.387 (7)	C11b—H1c11b	0.96
C5a—H1c5a	0.96	C12b—C13b	1.383 (5)
C6a—C7a	1.369 (5)	C12b—H1c12b	0.96
C6a—H1c6a	0.96	C13b—C14b	1.381 (4)
C8a—C9a	1.531 (5)	C13b—H1c13b	0.96
C8a—C10a	1.526 (4)	C14b—C15b	1.380 (4)
C8a—H1c8a	0.9601	C14b—H1c14b	0.96
C9a—H1c9a	0.96	C15b—H1c15b	0.96
C9a—H2c9a	0.96	C16b—C17b	1.526 (5)
C9a—H3c9a	0.9599	C16b—C18b	1.516 (4)
C10a—C11a	1.390 (4)	C16b—H1c16b	0.96
C10a—C15a	1.387 (4)	C17b—H1c17b	0.96
C11a—C12a	1.380 (5)	C17b—H2c17b	0.96
C11a—H1c11a	0.96	C17b—H3c17b	0.96
C12a—C13a	1.398 (5)	C18b—C19b	1.394 (4)
C12a—H1c12a	0.96	C18b—C23b	1.389 (5)
C13a—C14a	1.367 (4)	C19b—C20b	1.380 (4)
C13a—H1c13a	0.96	C19b—H1c19b	0.9601
C14a—C15a	1.391 (4)	C20b—C21b	1.382 (6)
C14a—H1c14a	0.96	C20b—H1c20b	0.96
C15a—H1c15a	0.96	C21b—C22b	1.395 (5)
C16a—C17a	1.532 (4)	C21b—H1c21b	0.96
C16a—C18a	1.528 (3)	C22b—C23b	1.381 (4)
C16a—H1c16a	0.9601	C22b—H1c22b	0.9599
C17a—H1c17a	0.96	C23b—H1c23b	0.96
O1a—P1a—N1a	103.50 (12)	C18a—C19a—C20a	120.1 (3)
O1a—P1a—N2a	115.22 (11)	C18a—C19a—H1c19a	119.96
O1a—P1a—N3a	115.23 (13)	C20a—C19a—H1c19a	119.97
N1a—P1a—N2a	109.74 (13)	C19a—C20a—C21a	121.4 (3)
N1a—P1a—N3a	109.45 (11)	C19a—C20a—H1c20a	119.3
N2a—P1a—N3a	103.69 (12)	C21a—C20a—H1c20a	119.3
O1b—P1b—N1b	103.20 (12)	C20a—C21a—C22a	118.8 (3)
O1b—P1b—N2b	116.02 (11)	C20a—C21a—H1c21a	120.59
O1b—P1b—N3b	116.30 (13)	C22a—C21a—H1c21a	120.59
N1b—P1b—N2b	109.56 (14)	C21a—C22a—C23a	120.2 (3)
N1b—P1b—N3b	109.49 (12)	C21a—C22a—H1c22a	119.88
N2b—P1b—N3b	102.25 (12)	C23a—C22a—H1c22a	119.87
P1a—N1a—C1a	124.0 (2)	C18a—C23a—C22a	121.1 (3)
P1a—N1a—H1n1a	119 (2)	C18a—C23a—H1c23a	119.46
C1a—N1a—H1n1a	117 (2)	C22a—C23a—H1c23a	119.46
P1a—N2a—C8a	123.39 (19)	O2b—C1b—N1b	123.0 (3)
P1a—N2a—H1n2a	113 (2)	O2b—C1b—C2b	121.8 (3)
C8a—N2a—H1n2a	118 (2)	N1b—C1b—C2b	115.1 (2)
P1a—N3a—C16a	123.52 (19)	C1b—C2b—C3b	123.6 (3)
P1a—N3a—H1n3a	114 (2)	C1b—C2b—C7b	121.8 (3)
C16a—N3a—H1n3a	122 (2)	C3b—C2b—C7b	114.5 (3)
P1b—N1b—C1b	126.2 (2)	F1b—C3b—C2b	117.4 (3)
P1b—N1b—H1n1b	116 (2)	F1b—C3b—C4b	118.2 (3)
C1b—N1b—H1n1b	118 (2)	C2b—C3b—C4b	124.4 (3)
P1b—N2b—C8b	125.02 (19)	C3b—C4b—C5b	118.4 (3)
P1b—N2b—H1n2b	113 (2)	C3b—C4b—H1c4b	120.78
C8b—N2b—H1n2b	118 (2)	C5b—C4b—H1c4b	120.78
P1b—N3b—C16b	123.6 (2)	C4b—C5b—C6b	120.1 (3)
P1b—N3b—H1n3b	114 (2)	C4b—C5b—H1c5b	119.93
C16b—N3b—H1n3b	123 (2)	C6b—C5b—H1c5b	119.94
O2a—C1a—N1a	121.2 (3)	C5b—C6b—C7b	118.8 (4)
O2a—C1a—C2a	120.9 (3)	C5b—C6b—H1c6b	120.62
N1a—C1a—C2a	117.9 (2)	C7b—C6b—H1c6b	120.62
C1a—C2a—C3a	123.4 (3)	F2b—C7b—C2b	117.4 (3)
C1a—C2a—C7a	121.3 (3)	F2b—C7b—C6b	118.9 (3)
C3a—C2a—C7a	115.2 (3)	C2b—C7b—C6b	123.7 (3)
F1a—C3a—C2a	117.7 (3)	N2b—C8b—C9b	111.8 (2)
F1a—C3a—C4a	118.9 (3)	N2b—C8b—C10b	111.1 (2)
C2a—C3a—C4a	123.4 (4)	N2b—C8b—H1c8b	107.37
C3a—C4a—C5a	118.8 (4)	C9b—C8b—C10b	111.3 (2)
C3a—C4a—H1c4a	120.59	C9b—C8b—H1c8b	107.17
C5a—C4a—H1c4a	120.6	C10b—C8b—H1c8b	107.86
C4a—C5a—C6a	120.7 (4)	C8b—C9b—H1c9b	109.47
C4a—C5a—H1c5a	119.62	C8b—C9b—H2c9b	109.47
C6a—C5a—H1c5a	119.63	C8b—C9b—H3c9b	109.47
C5a—C6a—C7a	118.3 (4)	H1c9b—C9b—H2c9b	109.47
C5a—C6a—H1c6a	120.84	H1c9b—C9b—H3c9b	109.47
C7a—C6a—H1c6a	120.84	H2c9b—C9b—H3c9b	109.48
F2a—C7a—C2a	117.6 (3)	C8b—C10b—C11b	119.6 (3)
F2a—C7a—C6a	118.9 (4)	C8b—C10b—C15b	122.4 (2)
C2a—C7a—C6a	123.5 (3)	C11b—C10b—C15b	118.0 (3)
N2a—C8a—C9a	112.6 (2)	C10b—C11b—C12b	121.0 (3)
N2a—C8a—C10a	111.5 (2)	C10b—C11b—H1c11b	119.49
N2a—C8a—H1c8a	105.99	C12b—C11b—H1c11b	119.49
C9a—C8a—C10a	109.9 (2)	C11b—C12b—C13b	120.4 (3)
C9a—C8a—H1c8a	107.72	C11b—C12b—H1c12b	119.78
C10a—C8a—H1c8a	108.89	C13b—C12b—H1c12b	119.78
C8a—C9a—H1c9a	109.47	C12b—C13b—C14b	118.8 (3)
C8a—C9a—H2c9a	109.47	C12b—C13b—H1c13b	120.59
C8a—C9a—H3c9a	109.47	C14b—C13b—H1c13b	120.59
H1c9a—C9a—H2c9a	109.47	C13b—C14b—C15b	121.0 (3)
H1c9a—C9a—H3c9a	109.48	C13b—C14b—H1c14b	119.48
H2c9a—C9a—H3c9a	109.48	C15b—C14b—H1c14b	119.49
C8a—C10a—C11a	118.3 (2)	C10b—C15b—C14b	120.7 (2)
C8a—C10a—C15a	122.6 (2)	C10b—C15b—H1c15b	119.66
C11a—C10a—C15a	119.0 (3)	C14b—C15b—H1c15b	119.66
C10a—C11a—C12a	121.0 (3)	N3b—C16b—C17b	109.1 (2)
C10a—C11a—H1c11a	119.53	N3b—C16b—C18b	113.4 (3)
C12a—C11a—H1c11a	119.52	N3b—C16b—H1c16b	107.21
C11a—C12a—C13a	119.5 (3)	C17b—C16b—C18b	110.0 (2)
C11a—C12a—H1c12a	120.22	C17b—C16b—H1c16b	110.75
C13a—C12a—H1c12a	120.23	C18b—C16b—H1c16b	106.25
C12a—C13a—C14a	119.6 (3)	C16b—C17b—H1c17b	109.47
C12a—C13a—H1c13a	120.18	C16b—C17b—H2c17b	109.47
C14a—C13a—H1c13a	120.18	C16b—C17b—H3c17b	109.47
C13a—C14a—C15a	120.9 (3)	H1c17b—C17b—H2c17b	109.47
C13a—C14a—H1c14a	119.55	H1c17b—C17b—H3c17b	109.47
C15a—C14a—H1c14a	119.56	H2c17b—C17b—H3c17b	109.47
C10a—C15a—C14a	119.9 (2)	C16b—C18b—C19b	118.5 (3)
C10a—C15a—H1c15a	120.03	C16b—C18b—C23b	123.4 (3)
C14a—C15a—H1c15a	120.03	C19b—C18b—C23b	118.0 (3)
N3a—C16a—C17a	109.0 (2)	C18b—C19b—C20b	121.2 (4)
N3a—C16a—C18a	113.1 (2)	C18b—C19b—H1c19b	119.39
N3a—C16a—H1c16a	108.16	C20b—C19b—H1c19b	119.39
C17a—C16a—C18a	111.8 (2)	C19b—C20b—C21b	120.4 (3)
C17a—C16a—H1c16a	109.5	C19b—C20b—H1c20b	119.82
C18a—C16a—H1c16a	105.08	C21b—C20b—H1c20b	119.83
C16a—C17a—H1c17a	109.47	C20b—C21b—C22b	119.1 (3)
C16a—C17a—H2c17a	109.47	C20b—C21b—H1c21b	120.45
C16a—C17a—H3c17a	109.47	C22b—C21b—H1c21b	120.46
H1c17a—C17a—H2c17a	109.47	C21b—C22b—C23b	120.2 (4)
H1c17a—C17a—H3c17a	109.47	C21b—C22b—H1c22b	119.9
H2c17a—C17a—H3c17a	109.47	C23b—C22b—H1c22b	119.9
C16a—C18a—C19a	122.1 (3)	C18b—C23b—C22b	121.1 (3)
C16a—C18a—C23a	119.5 (3)	C18b—C23b—H1c23b	119.45
C19a—C18a—C23a	118.4 (2)	C22b—C23b—H1c23b	119.46
P1a—N2a—C8a—C9a	88.4 (3)	O1a—P1a—N3a—C16a	−25.2 (3)
P1b—N2b—C8b—C9b	100.4 (3)	O1b—P1b—N3b—C16b	−41.6 (3)
P1a—N3a—C16a—C17a	117.7 (2)	P1a—N1a—C1a—O2a	−2.2 (3)
P1b—N3b—C16b—C17b	121.6 (3)	P1b—N1b—C1b—O2b	1.0 (3)
O1a—P1a—N1a—C1a	−176.68 (19)	P1a—N2a—C8a—C10a	−147.5 (2)
O1b—P1b—N1b—C1b	−178.4 (2)	P1b—N2b—C8b—C10b	−134.6 (2)
O1a—P1a—N2a—C8a	51.6 (3)	P1a—N3a—C16a—C18a	−117.2 (2)
O1b—P1b—N2b—C8b	55.9 (3)	P1b—N3b—C16b—C18b	−115.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1a—H1n1a···O2b	0.86 (2)	2.019 (18)	2.874 (3)	172 (3)
N2a—H1n2a···O1b^i	0.860 (9)	2.111 (11)	2.919 (3)	156 (3)
N3a—H1n3a···O1b^i	0.86 (2)	2.12 (3)	2.942 (3)	160 (3)
N1b—H1n1b···O2a^ii	0.860 (17)	1.967 (15)	2.822 (3)	173 (3)
N2b—H1n2b···O1a	0.860 (14)	2.036 (13)	2.868 (3)	163 (3)
N3b—H1n3b···O1a	0.86 (2)	2.06 (3)	2.888 (3)	163 (3)
C5a—H1c5a···O1a^iii	0.96	2.35	3.278 (4)	162.01

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

C23H24F2N3O2P	Z = 2
Mr = 443.4	F(000) = 464
Triclinic, P1	Dx = 1.338 Mg m^−3
Hall symbol: P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.7524 (2) Å	Cell parameters from 12269 reflections
b = 10.6117 (2) Å	θ = 4.1–69.2°
c = 11.2510 (2) Å	µ = 1.46 mm^−1
α = 77.3381 (15)°	T = 95 K
β = 75.6221 (16)°	Prism, colourless
γ = 87.7313 (16)°	0.29 × 0.09 × 0.07 mm
V = 1100.33 (4) Å^3

Data collection

Agilent SuperNova Dual Source diffractometer with an AtlasS2 detector	7660 independent reflections
Radiation source: X-ray tube	7383 reflections with I > 3σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 5.2027 pixels mm^-1	θmax = 69.4°, θmin = 4.2°
ω scans	h = −10→11
Absorption correction: analytical (CrysAlis PRO; Rigaku OD, 2015)	k = −12→12
Tmin = 0.774, Tmax = 0.917	l = −13→13
16006 measured reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F > 3σ(F)] = 0.039	Weighting scheme based on measured s.u.'s w = 1/(σ^2(I) + 0.0016I^2)
wR(F) = 0.098	(Δ/σ)max = 0.030
S = 1.50	Δρmax = 0.17 e Å^−3
7660 reflections	Δρmin = −0.22 e Å^−3
578 parameters	Absolute structure: 3604 of Friedel pairs used in the refinement
6 restraints	Absolute structure parameter: −0.014 (14)
177 constraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1a	0.56995 (6)	0.29619 (5)	0.11407 (5)	0.01258 (15)
P1b	0.06956 (6)	0.29985 (5)	0.12175 (5)	0.01314 (15)
F1a	0.49063 (16)	0.69491 (13)	−0.06133 (13)	0.0322 (5)
F2a	0.64829 (18)	0.67228 (15)	0.30505 (13)	0.0384 (6)
F1b	−0.03241 (15)	0.67855 (12)	−0.06760 (12)	0.0244 (4)
F2b	0.14485 (18)	0.70701 (14)	0.27756 (15)	0.0376 (6)
O1a	0.43627 (16)	0.23908 (13)	0.10831 (13)	0.0161 (5)
O2a	0.74221 (16)	0.51377 (14)	0.12918 (15)	0.0215 (5)
O1b	−0.06848 (16)	0.23999 (13)	0.13222 (13)	0.0171 (5)
O2b	0.24662 (16)	0.53595 (14)	0.10757 (15)	0.0220 (5)
N1a	0.52918 (19)	0.45461 (16)	0.11171 (16)	0.0156 (5)
N2a	0.62725 (19)	0.23425 (16)	0.23755 (15)	0.0151 (5)
N3a	0.70464 (19)	0.28615 (17)	−0.00128 (16)	0.0161 (5)
N1b	0.02925 (19)	0.45795 (17)	0.11576 (17)	0.0170 (6)
N2b	0.14445 (19)	0.24619 (16)	0.23590 (16)	0.0156 (5)
N3b	0.1948 (2)	0.28665 (18)	0.00034 (16)	0.0175 (6)
C1a	0.6214 (2)	0.5421 (2)	0.12087 (19)	0.0164 (6)
C2a	0.5677 (2)	0.6759 (2)	0.1237 (2)	0.0201 (7)
C3a	0.5037 (3)	0.7481 (2)	0.0341 (2)	0.0263 (8)
C4a	0.4576 (3)	0.8722 (2)	0.0364 (3)	0.0398 (10)
C5a	0.4753 (3)	0.9279 (2)	0.1307 (3)	0.0465 (11)
C6a	0.5401 (3)	0.8611 (2)	0.2227 (3)	0.0404 (10)
C7a	0.5858 (3)	0.7377 (2)	0.2164 (2)	0.0283 (8)
C8a	0.5386 (2)	0.21972 (19)	0.36624 (18)	0.0171 (7)
C9a	0.5444 (3)	0.3396 (2)	0.4199 (2)	0.0258 (8)
C10a	0.5794 (2)	0.10097 (19)	0.45365 (18)	0.0173 (7)
C11a	0.4765 (3)	0.0426 (2)	0.5600 (2)	0.0256 (7)
C12a	0.5104 (3)	−0.0605 (2)	0.6464 (2)	0.0330 (8)
C13a	0.6473 (3)	−0.1063 (2)	0.6292 (2)	0.0312 (8)
C14a	0.7496 (3)	−0.0495 (2)	0.5234 (2)	0.0285 (8)
C15a	0.7155 (2)	0.0531 (2)	0.4358 (2)	0.0224 (7)
C16a	0.6926 (2)	0.27494 (19)	−0.12562 (18)	0.0167 (6)
C17a	0.7548 (3)	0.1462 (2)	−0.1518 (2)	0.0234 (7)
C18a	0.7592 (2)	0.38947 (19)	−0.22965 (19)	0.0176 (7)
C19a	0.8193 (2)	0.4951 (2)	−0.2049 (2)	0.0212 (7)
C20a	0.8750 (3)	0.5991 (2)	−0.3023 (2)	0.0275 (8)
C21a	0.8718 (3)	0.6005 (2)	−0.4246 (2)	0.0275 (8)
C22a	0.8103 (3)	0.4961 (2)	−0.4499 (2)	0.0272 (8)
C23a	0.7555 (2)	0.3923 (2)	−0.3536 (2)	0.0235 (7)
C1b	0.1223 (2)	0.5539 (2)	0.10859 (18)	0.0166 (7)
C2b	0.0578 (2)	0.68541 (19)	0.1059 (2)	0.0177 (7)
C3b	−0.0204 (2)	0.7421 (2)	0.02101 (19)	0.0187 (7)
C4b	−0.0835 (3)	0.8603 (2)	0.0210 (2)	0.0246 (7)
C5b	−0.0678 (3)	0.9280 (2)	0.1089 (2)	0.0281 (8)
C6b	0.0107 (3)	0.8774 (2)	0.1950 (2)	0.0327 (9)
C7b	0.0715 (3)	0.7579 (2)	0.1917 (2)	0.0246 (8)
C8b	0.0778 (2)	0.24297 (19)	0.36791 (18)	0.0178 (7)
C9b	0.1309 (3)	0.3555 (2)	0.4108 (2)	0.0253 (7)
C10b	0.1009 (2)	0.1136 (2)	0.45054 (19)	0.0178 (7)
C11b	0.0436 (3)	0.0910 (2)	0.5800 (2)	0.0260 (7)
C12b	0.0627 (3)	−0.0255 (2)	0.6578 (2)	0.0277 (8)
C13b	0.1401 (3)	−0.1223 (2)	0.6088 (2)	0.0270 (8)
C14b	0.1980 (3)	−0.1008 (2)	0.4801 (2)	0.0267 (8)
C15b	0.1790 (2)	0.0156 (2)	0.40209 (19)	0.0218 (7)
C16b	0.1742 (2)	0.3030 (2)	−0.12632 (19)	0.0214 (7)
C17b	0.2172 (3)	0.1792 (2)	−0.1735 (2)	0.0365 (9)
C18b	0.2550 (2)	0.4184 (2)	−0.21891 (19)	0.0196 (7)
C19b	0.2153 (3)	0.4637 (2)	−0.3311 (2)	0.0269 (8)
C20b	0.2915 (3)	0.5613 (2)	−0.4233 (2)	0.0337 (9)
C21b	0.4089 (3)	0.6167 (2)	−0.4052 (2)	0.0334 (9)
C22b	0.4476 (3)	0.5742 (2)	−0.2924 (2)	0.0298 (8)
C23b	0.3701 (3)	0.4758 (2)	−0.1995 (2)	0.0238 (7)
H1c4a	0.413696	0.919017	−0.027196	0.0478*
H1c5a	0.44259	1.013983	0.133401	0.0559*
H1c6a	0.552669	0.900101	0.288714	0.0484*
H1c8a	0.443119	0.208923	0.361198	0.0205*
H1c9a	0.487622	0.324487	0.504835	0.0309*
H2c9a	0.640552	0.357035	0.418827	0.0309*
H3c9a	0.508482	0.412272	0.36983	0.0309*
H1c11a	0.381568	0.074289	0.573319	0.0308*
H1c12a	0.438556	−0.100546	0.718595	0.0396*
H1c13a	0.671006	−0.17667	0.690061	0.0375*
H1c14a	0.844563	−0.081291	0.510522	0.0342*
H1c15a	0.786928	0.091158	0.362345	0.0269*
H1c16a	0.594075	0.276444	−0.12536	0.02*
H1c17a	0.742329	0.13601	−0.231136	0.028*
H2c17a	0.853919	0.145249	−0.154167	0.028*
H3c17a	0.707144	0.076649	−0.086357	0.028*
H1c19a	0.822149	0.496072	−0.12043	0.0254*
H1c20a	0.916377	0.671138	−0.284225	0.033*
H1c21a	0.911381	0.672317	−0.49121	0.033*
H1c22a	0.806024	0.496343	−0.53433	0.0327*
H1c23a	0.714082	0.320584	−0.372205	0.0282*
H1c4b	−0.13747	0.895182	−0.038952	0.0295*
H1c5b	−0.111496	1.010522	0.110254	0.0338*
H1c6b	0.022672	0.924411	0.255697	0.0392*
H1c8b	−0.022252	0.252785	0.37658	0.0214*
H1c9b	0.07756	0.357345	0.494463	0.0303*
H2c9b	0.229297	0.344342	0.409801	0.0303*
H3c9b	0.119049	0.435372	0.354842	0.0303*
H1c11b	−0.010042	0.157325	0.61581	0.0312*
H1c12b	0.021655	−0.039111	0.746554	0.0333*
H1c13b	0.153655	−0.202887	0.662869	0.0325*
H1c14b	0.251796	−0.167404	0.444865	0.0321*
H1c15b	0.220237	0.028844	0.31336	0.0262*
H1c16b	0.07572	0.319982	−0.121146	0.0257*
H1c17b	0.206173	0.190041	−0.257602	0.0438*
H2c17b	0.314294	0.16119	−0.172967	0.0438*
H3c17b	0.158091	0.108701	−0.119636	0.0438*
H1c19b	0.133719	0.426594	−0.344647	0.0323*
H1c20b	0.262897	0.590967	−0.500341	0.0404*
H1c21b	0.462776	0.683548	−0.469753	0.0401*
H1c22b	0.528053	0.612603	−0.278421	0.0358*
H1c23b	0.396857	0.447694	−0.121396	0.0286*
H1n1a	0.4466 (15)	0.481 (2)	0.103 (3)	0.0187*
H1n2a	0.7166 (11)	0.244 (3)	0.228 (2)	0.0182*
H1n3a	0.7867 (15)	0.281 (3)	0.015 (2)	0.0193*
H1n1b	−0.0566 (14)	0.481 (3)	0.115 (3)	0.0204*
H1n2b	0.2351 (10)	0.246 (3)	0.217 (2)	0.0187*
H1n3b	0.2793 (15)	0.274 (3)	0.011 (3)	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1a	0.0123 (2)	0.0121 (2)	0.0137 (2)	0.00083 (16)	−0.00338 (18)	−0.00343 (17)
P1b	0.0126 (2)	0.0130 (2)	0.0142 (2)	0.00084 (17)	−0.00369 (18)	−0.00329 (17)
F1a	0.0372 (8)	0.0269 (7)	0.0317 (7)	−0.0001 (6)	−0.0154 (6)	0.0032 (6)
F2a	0.0520 (10)	0.0373 (8)	0.0316 (8)	−0.0070 (7)	−0.0123 (7)	−0.0156 (6)
F1b	0.0331 (8)	0.0215 (6)	0.0225 (6)	0.0036 (5)	−0.0126 (5)	−0.0070 (5)
F2b	0.0508 (10)	0.0352 (8)	0.0397 (8)	0.0061 (7)	−0.0294 (7)	−0.0157 (6)
O1a	0.0147 (7)	0.0156 (7)	0.0189 (7)	0.0006 (5)	−0.0045 (6)	−0.0053 (5)
O2a	0.0150 (8)	0.0206 (7)	0.0311 (8)	0.0015 (6)	−0.0076 (6)	−0.0082 (6)
O1b	0.0155 (7)	0.0160 (7)	0.0205 (7)	0.0007 (5)	−0.0050 (6)	−0.0047 (5)
O2b	0.0155 (8)	0.0214 (8)	0.0301 (8)	−0.0001 (6)	−0.0071 (6)	−0.0060 (6)
N1a	0.0123 (9)	0.0147 (8)	0.0208 (8)	0.0016 (6)	−0.0055 (7)	−0.0047 (6)
N2a	0.0124 (9)	0.0176 (8)	0.0146 (8)	0.0003 (6)	−0.0027 (7)	−0.0026 (6)
N3a	0.0134 (9)	0.0203 (8)	0.0157 (8)	0.0024 (7)	−0.0048 (7)	−0.0055 (6)
N1b	0.0115 (9)	0.0162 (8)	0.0242 (8)	0.0008 (7)	−0.0062 (7)	−0.0047 (7)
N2b	0.0122 (9)	0.0200 (8)	0.0145 (8)	0.0018 (7)	−0.0027 (7)	−0.0045 (6)
N3b	0.0139 (9)	0.0251 (9)	0.0144 (8)	0.0017 (7)	−0.0049 (7)	−0.0047 (7)
C1a	0.0167 (11)	0.0160 (9)	0.0157 (9)	0.0005 (8)	−0.0032 (8)	−0.0022 (7)
C2a	0.0172 (11)	0.0145 (10)	0.0261 (11)	−0.0016 (8)	0.0008 (8)	−0.0059 (8)
C3a	0.0219 (12)	0.0180 (10)	0.0337 (12)	−0.0011 (9)	−0.0025 (10)	0.0009 (9)
C4a	0.0305 (15)	0.0163 (12)	0.0611 (18)	0.0017 (10)	−0.0012 (13)	0.0042 (11)
C5a	0.0372 (16)	0.0127 (11)	0.073 (2)	0.0004 (10)	0.0163 (14)	−0.0083 (12)
C6a	0.0393 (16)	0.0259 (13)	0.0505 (17)	−0.0107 (11)	0.0131 (13)	−0.0226 (12)
C7a	0.0271 (13)	0.0231 (11)	0.0310 (12)	−0.0069 (9)	0.0041 (10)	−0.0096 (9)
C8a	0.0160 (11)	0.0189 (10)	0.0162 (10)	0.0015 (8)	−0.0036 (8)	−0.0042 (8)
C9a	0.0404 (14)	0.0202 (11)	0.0187 (10)	0.0051 (9)	−0.0088 (9)	−0.0074 (8)
C10a	0.0206 (11)	0.0170 (10)	0.0159 (9)	−0.0007 (8)	−0.0064 (8)	−0.0046 (8)
C11a	0.0238 (12)	0.0271 (11)	0.0221 (10)	−0.0008 (9)	−0.0016 (9)	−0.0016 (8)
C12a	0.0342 (15)	0.0308 (13)	0.0250 (12)	−0.0021 (10)	−0.0008 (10)	0.0059 (9)
C13a	0.0369 (14)	0.0241 (12)	0.0300 (12)	−0.0001 (10)	−0.0133 (11)	0.0056 (9)
C14a	0.0257 (13)	0.0235 (11)	0.0340 (12)	0.0001 (9)	−0.0103 (10)	0.0020 (9)
C15a	0.0205 (11)	0.0205 (10)	0.0239 (11)	0.0001 (8)	−0.0054 (9)	0.0001 (8)
C16a	0.0163 (11)	0.0197 (10)	0.0154 (9)	0.0004 (8)	−0.0052 (8)	−0.0053 (8)
C17a	0.0303 (13)	0.0169 (10)	0.0200 (10)	−0.0007 (9)	0.0003 (9)	−0.0051 (8)
C18a	0.0173 (11)	0.0169 (10)	0.0178 (10)	0.0039 (8)	−0.0045 (8)	−0.0030 (8)
C19a	0.0221 (11)	0.0216 (10)	0.0199 (10)	−0.0005 (8)	−0.0055 (9)	−0.0043 (8)
C20a	0.0306 (13)	0.0225 (11)	0.0284 (12)	−0.0042 (9)	−0.0055 (10)	−0.0045 (9)
C21a	0.0296 (13)	0.0227 (11)	0.0244 (11)	0.0003 (9)	−0.0035 (9)	0.0034 (9)
C22a	0.0339 (13)	0.0281 (11)	0.0182 (10)	0.0015 (9)	−0.0072 (9)	−0.0011 (9)
C23a	0.0279 (12)	0.0229 (11)	0.0208 (10)	−0.0008 (9)	−0.0085 (9)	−0.0036 (8)
C1b	0.0162 (11)	0.0170 (10)	0.0169 (9)	0.0003 (8)	−0.0044 (8)	−0.0037 (8)
C2b	0.0165 (11)	0.0153 (10)	0.0210 (10)	−0.0016 (8)	−0.0034 (8)	−0.0040 (8)
C3b	0.0205 (11)	0.0163 (10)	0.0187 (10)	−0.0025 (8)	−0.0033 (8)	−0.0035 (8)
C4b	0.0262 (13)	0.0167 (10)	0.0277 (11)	0.0014 (8)	−0.0058 (9)	0.0006 (8)
C5b	0.0312 (14)	0.0148 (10)	0.0355 (12)	0.0013 (9)	−0.0024 (10)	−0.0060 (9)
C6b	0.0413 (15)	0.0239 (12)	0.0362 (13)	−0.0004 (10)	−0.0082 (11)	−0.0150 (10)
C7b	0.0291 (13)	0.0215 (11)	0.0266 (11)	−0.0016 (9)	−0.0108 (10)	−0.0076 (9)
C8b	0.0174 (11)	0.0214 (10)	0.0152 (9)	0.0030 (8)	−0.0028 (8)	−0.0068 (8)
C9b	0.0348 (14)	0.0224 (11)	0.0218 (10)	0.0042 (9)	−0.0100 (9)	−0.0086 (8)
C10b	0.0147 (10)	0.0232 (11)	0.0168 (10)	−0.0027 (8)	−0.0060 (8)	−0.0041 (8)
C11b	0.0257 (12)	0.0324 (12)	0.0180 (10)	0.0021 (9)	−0.0011 (9)	−0.0065 (9)
C12b	0.0297 (13)	0.0342 (12)	0.0160 (10)	−0.0052 (10)	−0.0030 (9)	−0.0004 (9)
C13b	0.0306 (13)	0.0245 (11)	0.0251 (11)	−0.0062 (9)	−0.0110 (10)	0.0025 (9)
C14b	0.0350 (14)	0.0210 (11)	0.0238 (11)	0.0007 (9)	−0.0062 (10)	−0.0053 (8)
C15b	0.0263 (12)	0.0216 (10)	0.0173 (10)	−0.0013 (8)	−0.0037 (8)	−0.0052 (8)
C16b	0.0211 (11)	0.0300 (12)	0.0155 (10)	−0.0014 (9)	−0.0064 (8)	−0.0071 (8)
C17b	0.0572 (18)	0.0270 (12)	0.0246 (12)	−0.0130 (11)	−0.0025 (11)	−0.0104 (9)
C18b	0.0225 (12)	0.0200 (10)	0.0174 (10)	0.0066 (8)	−0.0055 (8)	−0.0070 (8)
C19b	0.0393 (15)	0.0257 (11)	0.0202 (10)	0.0065 (10)	−0.0127 (10)	−0.0094 (9)
C20b	0.0564 (18)	0.0265 (12)	0.0196 (11)	0.0109 (11)	−0.0132 (11)	−0.0054 (9)
C21b	0.0483 (17)	0.0204 (11)	0.0224 (11)	0.0043 (10)	0.0021 (11)	0.0017 (9)
C22b	0.0282 (13)	0.0240 (11)	0.0323 (12)	0.0013 (10)	−0.0036 (10)	−0.0002 (9)
C23b	0.0249 (12)	0.0247 (11)	0.0194 (10)	0.0021 (9)	−0.0067 (9)	0.0017 (8)

Geometric parameters (Å, º)

P1a—O1a	1.4808 (17)	C17a—H2c17a	0.9599
P1a—N1a	1.7081 (18)	C17a—H3c17a	0.96
P1a—N2a	1.6219 (19)	C18a—C19a	1.396 (3)
P1a—N3a	1.6199 (17)	C18a—C23a	1.398 (3)
P1b—O1b	1.4784 (17)	C19a—C20a	1.391 (3)
P1b—N1b	1.6986 (19)	C19a—H1c19a	0.9599
P1b—N2b	1.618 (2)	C20a—C21a	1.380 (4)
P1b—N3b	1.6181 (17)	C20a—H1c20a	0.9599
F1a—C3a	1.352 (3)	C21a—C22a	1.395 (4)
F2a—C7a	1.346 (3)	C21a—H1c21a	0.96
F1b—C3b	1.349 (3)	C22a—C23a	1.382 (3)
F2b—C7b	1.349 (3)	C22a—H1c22a	0.9601
O2a—C1a	1.225 (3)	C23a—H1c23a	0.9601
O2b—C1b	1.218 (3)	C1b—C2b	1.505 (3)
N1a—C1a	1.355 (3)	C2b—C3b	1.390 (3)
N1a—H1n1a	0.862 (18)	C2b—C7b	1.392 (4)
N2a—C8a	1.469 (2)	C3b—C4b	1.375 (3)
N2a—H1n2a	0.859 (12)	C4b—C5b	1.383 (4)
N3a—C16a	1.463 (3)	C4b—H1c4b	0.9601
N3a—H1n3a	0.861 (19)	C5b—C6b	1.386 (4)
N1b—C1b	1.367 (3)	C5b—H1c5b	0.96
N1b—H1n1b	0.865 (16)	C6b—C7b	1.383 (3)
N2b—C8b	1.459 (3)	C6b—H1c6b	0.9599
N2b—H1n2b	0.856 (10)	C8b—C9b	1.534 (3)
N3b—C16b	1.460 (3)	C8b—C10b	1.523 (3)
N3b—H1n3b	0.861 (17)	C8b—H1c8b	0.9601
C1a—C2a	1.498 (3)	C9b—H1c9b	0.96
C2a—C3a	1.389 (3)	C9b—H2c9b	0.9599
C2a—C7a	1.396 (4)	C9b—H3c9b	0.96
C3a—C4a	1.378 (3)	C10b—C11b	1.395 (3)
C4a—C5a	1.370 (5)	C10b—C15b	1.393 (3)
C4a—H1c4a	0.9601	C11b—C12b	1.384 (3)
C5a—C6a	1.393 (5)	C11b—H1c11b	0.96
C5a—H1c5a	0.96	C12b—C13b	1.382 (4)
C6a—C7a	1.377 (4)	C12b—H1c12b	0.96
C6a—H1c6a	0.9599	C13b—C14b	1.388 (3)
C8a—C9a	1.531 (3)	C13b—H1c13b	0.96
C8a—C10a	1.525 (3)	C14b—C15b	1.385 (3)
C8a—H1c8a	0.9601	C14b—H1c14b	0.96
C9a—H1c9a	0.96	C15b—H1c15b	0.96
C9a—H2c9a	0.9599	C16b—C17b	1.528 (4)
C9a—H3c9a	0.96	C16b—C18b	1.521 (3)
C10a—C11a	1.397 (3)	C16b—H1c16b	0.9601
C10a—C15a	1.385 (3)	C17b—H1c17b	0.9601
C11a—C12a	1.384 (3)	C17b—H2c17b	0.9599
C11a—H1c11a	0.9601	C17b—H3c17b	0.9601
C12a—C13a	1.384 (4)	C18b—C19b	1.392 (3)
C12a—H1c12a	0.9601	C18b—C23b	1.383 (4)
C13a—C14a	1.385 (3)	C19b—C20b	1.381 (3)
C13a—H1c13a	0.96	C19b—H1c19b	0.9601
C14a—C15a	1.390 (3)	C20b—C21b	1.385 (4)
C14a—H1c14a	0.9599	C20b—H1c20b	0.9601
C15a—H1c15a	0.9599	C21b—C22b	1.389 (4)
C16a—C17a	1.530 (3)	C21b—H1c21b	0.96
C16a—C18a	1.526 (2)	C22b—C23b	1.395 (3)
C16a—H1c16a	0.9601	C22b—H1c22b	0.9599
C17a—H1c17a	0.9601	C23b—H1c23b	0.9599
O1a—P1a—N1a	103.29 (9)	C18a—C19a—C20a	120.2 (2)
O1a—P1a—N2a	115.49 (8)	C18a—C19a—H1c19a	119.9
O1a—P1a—N3a	115.08 (10)	C20a—C19a—H1c19a	119.91
N1a—P1a—N2a	109.87 (10)	C19a—C20a—C21a	121.1 (2)
N1a—P1a—N3a	109.77 (8)	C19a—C20a—H1c20a	119.45
N2a—P1a—N3a	103.37 (9)	C21a—C20a—H1c20a	119.45
O1b—P1b—N1b	102.89 (9)	C20a—C21a—C22a	119.1 (2)
O1b—P1b—N2b	116.28 (8)	C20a—C21a—H1c21a	120.44
O1b—P1b—N3b	116.30 (10)	C22a—C21a—H1c21a	120.43
N1b—P1b—N2b	109.74 (10)	C21a—C22a—C23a	120.0 (2)
N1b—P1b—N3b	109.71 (9)	C21a—C22a—H1c22a	120.01
N2b—P1b—N3b	101.94 (10)	C23a—C22a—H1c22a	120
P1a—N1a—C1a	123.03 (15)	C18a—C23a—C22a	121.4 (2)
P1a—N1a—H1n1a	118.7 (18)	C18a—C23a—H1c23a	119.33
C1a—N1a—H1n1a	118.3 (18)	C22a—C23a—H1c23a	119.32
P1a—N2a—C8a	122.96 (14)	O2b—C1b—N1b	123.66 (19)
P1a—N2a—H1n2a	114.9 (17)	O2b—C1b—C2b	121.8 (2)
C8a—N2a—H1n2a	116.2 (18)	N1b—C1b—C2b	114.51 (19)
P1a—N3a—C16a	123.75 (16)	C1b—C2b—C3b	123.3 (2)
P1a—N3a—H1n3a	116.7 (17)	C1b—C2b—C7b	121.3 (2)
C16a—N3a—H1n3a	119.4 (18)	C3b—C2b—C7b	115.4 (2)
P1b—N1b—C1b	125.57 (16)	F1b—C3b—C2b	118.00 (19)
P1b—N1b—H1n1b	118.1 (18)	F1b—C3b—C4b	118.5 (2)
C1b—N1b—H1n1b	116.3 (18)	C2b—C3b—C4b	123.5 (2)
P1b—N2b—C8b	124.36 (15)	C3b—C4b—C5b	118.9 (2)
P1b—N2b—H1n2b	116.7 (17)	C3b—C4b—H1c4b	120.55
C8b—N2b—H1n2b	115.1 (18)	C5b—C4b—H1c4b	120.55
P1b—N3b—C16b	123.82 (16)	C4b—C5b—C6b	120.3 (2)
P1b—N3b—H1n3b	117.7 (19)	C4b—C5b—H1c5b	119.82
C16b—N3b—H1n3b	118.4 (18)	C6b—C5b—H1c5b	119.83
O2a—C1a—N1a	122.3 (2)	C5b—C6b—C7b	118.6 (3)
O2a—C1a—C2a	120.9 (2)	C5b—C6b—H1c6b	120.69
N1a—C1a—C2a	116.76 (19)	C7b—C6b—H1c6b	120.7
C1a—C2a—C3a	123.5 (2)	F2b—C7b—C2b	118.1 (2)
C1a—C2a—C7a	120.6 (2)	F2b—C7b—C6b	118.7 (2)
C3a—C2a—C7a	115.8 (2)	C2b—C7b—C6b	123.2 (2)
F1a—C3a—C2a	118.0 (2)	N2b—C8b—C9b	111.10 (16)
F1a—C3a—C4a	119.0 (2)	N2b—C8b—C10b	110.97 (17)
C2a—C3a—C4a	122.9 (3)	N2b—C8b—H1c8b	107.94
C3a—C4a—C5a	119.1 (3)	C9b—C8b—C10b	111.28 (19)
C3a—C4a—H1c4a	120.45	C9b—C8b—H1c8b	107.62
C5a—C4a—H1c4a	120.46	C10b—C8b—H1c8b	107.75
C4a—C5a—C6a	120.8 (2)	C8b—C9b—H1c9b	109.47
C4a—C5a—H1c5a	119.58	C8b—C9b—H2c9b	109.47
C6a—C5a—H1c5a	119.59	C8b—C9b—H3c9b	109.47
C5a—C6a—C7a	118.2 (3)	H1c9b—C9b—H2c9b	109.48
C5a—C6a—H1c6a	120.88	H1c9b—C9b—H3c9b	109.47
C7a—C6a—H1c6a	120.88	H2c9b—C9b—H3c9b	109.48
F2a—C7a—C2a	118.2 (2)	C8b—C10b—C11b	119.68 (19)
F2a—C7a—C6a	118.7 (3)	C8b—C10b—C15b	122.50 (17)
C2a—C7a—C6a	123.1 (3)	C11b—C10b—C15b	117.82 (19)
N2a—C8a—C9a	112.49 (16)	C10b—C11b—C12b	121.1 (2)
N2a—C8a—C10a	111.31 (16)	C10b—C11b—H1c11b	119.44
N2a—C8a—H1c8a	106.17	C12b—C11b—H1c11b	119.44
C9a—C8a—C10a	109.74 (18)	C11b—C12b—C13b	120.6 (2)
C9a—C8a—H1c8a	107.86	C11b—C12b—H1c12b	119.67
C10a—C8a—H1c8a	109.12	C13b—C12b—H1c12b	119.68
C8a—C9a—H1c9a	109.47	C12b—C13b—C14b	118.8 (2)
C8a—C9a—H2c9a	109.47	C12b—C13b—H1c13b	120.61
C8a—C9a—H3c9a	109.47	C14b—C13b—H1c13b	120.61
H1c9a—C9a—H2c9a	109.48	C13b—C14b—C15b	120.7 (2)
H1c9a—C9a—H3c9a	109.47	C13b—C14b—H1c14b	119.66
H2c9a—C9a—H3c9a	109.48	C15b—C14b—H1c14b	119.66
C8a—C10a—C11a	118.23 (19)	C10b—C15b—C14b	120.92 (19)
C8a—C10a—C15a	122.90 (16)	C10b—C15b—H1c15b	119.54
C11a—C10a—C15a	118.77 (19)	C14b—C15b—H1c15b	119.54
C10a—C11a—C12a	120.5 (2)	N3b—C16b—C17b	108.99 (18)
C10a—C11a—H1c11a	119.75	N3b—C16b—C18b	113.5 (2)
C12a—C11a—H1c11a	119.75	N3b—C16b—H1c16b	107.25
C11a—C12a—C13a	120.4 (2)	C17b—C16b—C18b	110.12 (17)
C11a—C12a—H1c12a	119.79	C17b—C16b—H1c16b	110.84
C13a—C12a—H1c12a	119.8	C18b—C16b—H1c16b	106.06
C12a—C13a—C14a	119.4 (2)	C16b—C17b—H1c17b	109.47
C12a—C13a—H1c13a	120.29	C16b—C17b—H2c17b	109.47
C14a—C13a—H1c13a	120.3	C16b—C17b—H3c17b	109.47
C13a—C14a—C15a	120.3 (2)	H1c17b—C17b—H2c17b	109.48
C13a—C14a—H1c14a	119.85	H1c17b—C17b—H3c17b	109.46
C15a—C14a—H1c14a	119.85	H2c17b—C17b—H3c17b	109.47
C10a—C15a—C14a	120.59 (18)	C16b—C18b—C19b	118.2 (2)
C10a—C15a—H1c15a	119.7	C16b—C18b—C23b	123.1 (2)
C14a—C15a—H1c15a	119.71	C19b—C18b—C23b	118.69 (19)
N3a—C16a—C17a	109.06 (17)	C18b—C19b—C20b	120.9 (3)
N3a—C16a—C18a	113.06 (18)	C18b—C19b—H1c19b	119.53
N3a—C16a—H1c16a	108.25	C20b—C19b—H1c19b	119.53
C17a—C16a—C18a	112.13 (16)	C19b—C20b—C21b	120.4 (2)
C17a—C16a—H1c16a	109.25	C19b—C20b—H1c20b	119.8
C18a—C16a—H1c16a	104.91	C21b—C20b—H1c20b	119.81
C16a—C17a—H1c17a	109.47	C20b—C21b—C22b	119.2 (2)
C16a—C17a—H2c17a	109.47	C20b—C21b—H1c21b	120.42
C16a—C17a—H3c17a	109.47	C22b—C21b—H1c21b	120.43
H1c17a—C17a—H2c17a	109.47	C21b—C22b—C23b	120.2 (3)
H1c17a—C17a—H3c17a	109.46	C21b—C22b—H1c22b	119.88
H2c17a—C17a—H3c17a	109.48	C23b—C22b—H1c22b	119.88
C16a—C18a—C19a	122.2 (2)	C18b—C23b—C22b	120.5 (2)
C16a—C18a—C23a	119.5 (2)	C18b—C23b—H1c23b	119.72
C19a—C18a—C23a	118.25 (18)	C22b—C23b—H1c23b	119.74
P1a—N2a—C8a—C9a	−88.5 (2)	O1a—P1a—N3a—C16a	25.1 (2)
P1b—N2b—C8b—C9b	−101.0 (2)	O1b—P1b—N3b—C16b	42.1 (2)
P1a—N3a—C16a—C17a	−117.68 (19)	P1a—N1a—C1a—O2a	1.4 (3)
P1b—N3b—C16b—C17b	−121.47 (19)	P1b—N1b—C1b—O2b	−1.2 (3)
O1a—P1a—N1a—C1a	177.16 (16)	P1a—N2a—C8a—C10a	147.93 (15)
O1b—P1b—N1b—C1b	178.46 (17)	P1b—N2b—C8b—C10b	134.66 (16)
O1a—P1a—N2a—C8a	−51.78 (19)	P1a—N3a—C16a—C18a	116.90 (18)
O1b—P1b—N2b—C8b	−55.44 (19)	P1b—N3b—C16b—C18b	115.40 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5a—H1c5a···O1a^i	0.96	2.34	3.271 (3)	162.23
N1a—H1n1a···O2b	0.862 (18)	2.006 (16)	2.863 (2)	173 (3)
N2a—H1n2a···O1b^ii	0.859 (12)	2.110 (12)	2.907 (2)	154 (3)
N3a—H1n3a···O1b^ii	0.861 (19)	2.13 (2)	2.938 (3)	155 (2)
N1b—H1n1b···O2a^iii	0.865 (16)	1.951 (14)	2.812 (2)	173 (2)
N2b—H1n2b···O1a	0.856 (10)	2.046 (13)	2.858 (2)	158 (3)
N3b—H1n3b···O1a	0.861 (17)	2.07 (2)	2.887 (3)	157 (2)

Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x−1, y, z.