The synergistic co-operation of N—H...O=P hydrogen bonds and C—H...OX weak inter­molecular inter­actions (X is =P or —C) in the (CH₃O)₂P(O)(NH–NHC₆F₅) amido­phospho­ester: a combined X-ray crystallographic and theoretical study

The asymmetric unit of O,O′-dimethyl [(2,3,4,5,6-penta­fluoro­phenyl)­hydrazin­yl]phospho­nate, C₈H₈F₅N₂O₃P, is composed of two symmetry-independent mol­ecules with significant differences in the orientations of the C₆F₅ and OMe groups. In the crystal structure, a one-dimensional assembly is mediated from classical N—H...O hydrogen bonds, which includes R₂²(8), D(2) and some higher-order graph-set motifs. By also considering weak C—H...O=P and C—H...O—C inter­molecular inter­actions, a two-dimensional network extends along the ab plane. The strengths of the hydrogen bonds were evaluated using quantum chemical calculations with the GAUSSIAN09 software package at the B3LYP/6-311G(d,p) level of theory. The LP(O) to σ*(NH) and σ*(CH) charge-transfer inter­actions were examined according to second-order perturbation theory in natural bond orbital (NBO) methodology. The hydrogen-bonded clusters of mol­ecules, including N—H...O and C—H...O inter­actions, were constructed as input files for the calculations and the strengths of the hydrogen bonds are as follows: N—H...O [R₂²(8)] > N—H...O [D(2)] > C—H...O. The decomposed fingerprint plots show that the contribution portions of the F...H/H...F contacts in both mol­ecules are the largest.

Computing details

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: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009).

O,O'-Dimethyl [(2,3,4,5,6-pentafluorophenylhydrazinyl]phosphonate

Crystal data

C8H8F5N2O3P	F(000) = 1232
Mr = 306.13	Dx = 1.773 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.5273 (2) Å	Cell parameters from 4434 reflections
b = 10.3266 (3) Å	θ = 3.4–32.6°
c = 21.1193 (5) Å	µ = 0.31 mm^−1
β = 92.647 (2)°	T = 173 K
V = 2293.46 (10) Å^3	Prism, light yellow
Z = 8	0.34 × 0.14 × 0.12 mm

Data collection

Rigaku Oxford diffraction diffractometer	7628 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	5724 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 16.0416 pixels mm^-1	θmax = 32.8°, θmin = 3.3°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −15→13
Tmin = 0.790, Tmax = 1.000	l = −31→31
18096 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0522P)^2 + 0.6442P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
7628 reflections	Δρmax = 0.50 e Å^−3
363 parameters	Δρmin = −0.49 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The crystal structure of (I) was determined by mounting a single crystal of the compound on a polymer loop and data were measured with a Rigaku-Oxford Diffraction Eos Gemini CCD X-ray diffractometer using CrysalisPro software (Rigaku, Oxford Diffraction, 2015) and equipped with graphite-monochromated Mo-Kα (λ = 0.71073 Å) radiation at 173 (2) K. The structure was solved by direct methods and refined using full-matrix least-squares based on F² using ShelXL-2018 (Sheldrick, 2015). In this structure, all non-hydrogen atoms were refined anisotropically.

An absorption correction was performed using CrysAlisRED (Rigaku, Oxford Diffraction, 2014) and all calculations were performed using SHELXTL2018 (Sheldrick, 2015). The structure was checked using PLATON (Spek, 2009). The crystal data and the details of the X-ray analysis are given in Table 1.

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

	x	y	z	Uiso*/Ueq
P1A	0.29657 (4)	0.48507 (4)	0.52274 (2)	0.02069 (9)
F1A	0.48805 (11)	0.85269 (10)	0.67135 (5)	0.0340 (2)
F2A	0.56022 (12)	0.84382 (12)	0.79508 (5)	0.0403 (3)
F3A	0.49519 (12)	0.63884 (13)	0.86735 (5)	0.0414 (3)
F4A	0.35451 (12)	0.44170 (12)	0.81350 (5)	0.0416 (3)
F5A	0.28185 (11)	0.44920 (11)	0.69095 (5)	0.0363 (3)
O1A	0.36850 (11)	0.39164 (12)	0.48608 (6)	0.0269 (3)
O2A	0.22388 (11)	0.59143 (13)	0.48207 (5)	0.0264 (3)
O3A	0.18808 (12)	0.41813 (13)	0.55819 (6)	0.0329 (3)
N1A	0.39446 (13)	0.55359 (14)	0.57569 (6)	0.0219 (3)
N2A	0.34352 (13)	0.65722 (14)	0.61198 (6)	0.0214 (3)
C1A	0.38299 (15)	0.65152 (16)	0.67655 (7)	0.0213 (3)
C2A	0.45274 (16)	0.75067 (16)	0.70596 (8)	0.0236 (3)
C3A	0.48964 (17)	0.74787 (17)	0.76964 (8)	0.0267 (3)
C4A	0.45659 (17)	0.64409 (19)	0.80618 (8)	0.0290 (4)
C5A	0.38668 (17)	0.54401 (18)	0.77878 (8)	0.0280 (3)
C6A	0.35049 (16)	0.54848 (17)	0.71505 (8)	0.0252 (3)
C7A	0.07731 (17)	0.4811 (2)	0.58031 (10)	0.0393 (5)
H7AA	0.049379	0.548366	0.550049	0.059*
H7AB	0.097577	0.520613	0.621741	0.059*
H7AC	0.009168	0.417343	0.584290	0.059*
C8A	0.2887 (2)	0.65158 (19)	0.43065 (8)	0.0331 (4)
H8AA	0.305475	0.586405	0.398354	0.050*
H8AB	0.369424	0.688628	0.447046	0.050*
H8AC	0.235210	0.720377	0.411789	0.050*
P1B	0.29165 (4)	−0.01756 (4)	0.51345 (2)	0.01901 (9)
F1B	0.28927 (11)	−0.05031 (10)	0.33505 (5)	0.0363 (3)
F2B	0.18421 (11)	−0.02633 (11)	0.21976 (5)	0.0366 (3)
F3B	0.04720 (11)	0.18652 (12)	0.18421 (5)	0.0395 (3)
F4B	0.02299 (12)	0.38349 (11)	0.26905 (6)	0.0416 (3)
F5B	0.13675 (11)	0.36714 (10)	0.38549 (5)	0.0340 (2)
O1B	0.38949 (11)	−0.11079 (12)	0.53644 (6)	0.0250 (2)
O2B	0.25057 (11)	0.08045 (13)	0.56556 (6)	0.0280 (3)
O3B	0.16148 (10)	−0.07478 (12)	0.48915 (5)	0.0250 (2)
N1B	0.34036 (13)	0.05876 (14)	0.45123 (6)	0.0227 (3)
N2B	0.26314 (14)	0.16082 (14)	0.42822 (6)	0.0232 (3)
C1B	0.21704 (14)	0.15938 (15)	0.36578 (7)	0.0193 (3)
C2B	0.22656 (15)	0.05979 (16)	0.32162 (8)	0.0231 (3)
C3B	0.17144 (16)	0.07106 (17)	0.26100 (8)	0.0247 (3)
C4B	0.10291 (16)	0.17953 (18)	0.24254 (8)	0.0264 (3)
C5B	0.09053 (16)	0.27815 (17)	0.28519 (8)	0.0261 (3)
C6B	0.14768 (15)	0.26777 (16)	0.34484 (8)	0.0228 (3)
C7B	0.07676 (16)	−0.13699 (18)	0.53186 (9)	0.0307 (4)
H7BA	0.005488	−0.176333	0.507328	0.046*
H7BB	0.044257	−0.072490	0.561052	0.046*
H7BC	0.123174	−0.204269	0.556096	0.046*
C8B	0.34889 (19)	0.1448 (2)	0.60413 (9)	0.0347 (4)
H8BA	0.411273	0.183151	0.576647	0.052*
H8BB	0.391296	0.081675	0.632588	0.052*
H8BC	0.310620	0.213042	0.629252	0.052*
H2A	0.3656 (19)	0.731 (2)	0.5941 (10)	0.028 (5)*
H1A	0.463 (2)	0.565 (2)	0.5635 (10)	0.029 (5)*
H1B	0.418 (2)	0.072 (2)	0.4499 (10)	0.033 (6)*
H2B	0.282 (2)	0.232 (2)	0.4424 (11)	0.038 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1A	0.01861 (17)	0.0234 (2)	0.02021 (18)	−0.00111 (15)	0.00272 (14)	−0.00122 (15)
F1A	0.0461 (6)	0.0287 (5)	0.0269 (5)	−0.0106 (5)	−0.0019 (5)	0.0053 (4)
F2A	0.0526 (7)	0.0401 (6)	0.0275 (5)	−0.0127 (6)	−0.0043 (5)	−0.0068 (5)
F3A	0.0534 (7)	0.0541 (8)	0.0164 (4)	−0.0055 (6)	−0.0030 (5)	0.0025 (5)
F4A	0.0614 (8)	0.0378 (6)	0.0258 (5)	−0.0077 (6)	0.0045 (5)	0.0114 (5)
F5A	0.0484 (6)	0.0313 (6)	0.0288 (5)	−0.0143 (5)	−0.0021 (5)	0.0027 (5)
O1A	0.0266 (6)	0.0257 (6)	0.0287 (6)	−0.0015 (5)	0.0036 (5)	−0.0061 (5)
O2A	0.0245 (5)	0.0335 (7)	0.0211 (5)	0.0041 (5)	0.0000 (4)	0.0008 (5)
O3A	0.0267 (6)	0.0333 (7)	0.0395 (7)	−0.0016 (5)	0.0105 (5)	0.0034 (6)
N1A	0.0193 (6)	0.0259 (7)	0.0206 (6)	0.0007 (5)	0.0025 (5)	−0.0018 (5)
N2A	0.0260 (6)	0.0212 (6)	0.0168 (6)	0.0022 (5)	0.0005 (5)	0.0011 (5)
C1A	0.0224 (7)	0.0225 (7)	0.0190 (6)	0.0024 (6)	0.0017 (6)	0.0002 (6)
C2A	0.0267 (7)	0.0236 (8)	0.0207 (7)	0.0005 (6)	0.0022 (6)	0.0015 (6)
C3A	0.0302 (8)	0.0285 (8)	0.0214 (7)	−0.0015 (7)	0.0000 (6)	−0.0037 (6)
C4A	0.0334 (8)	0.0365 (10)	0.0172 (7)	0.0040 (7)	0.0015 (6)	0.0009 (7)
C5A	0.0344 (9)	0.0291 (9)	0.0207 (7)	−0.0001 (7)	0.0046 (7)	0.0055 (7)
C6A	0.0306 (8)	0.0240 (8)	0.0212 (7)	−0.0017 (7)	0.0020 (6)	−0.0002 (6)
C7A	0.0248 (8)	0.0548 (13)	0.0390 (10)	0.0008 (9)	0.0087 (8)	0.0026 (10)
C8A	0.0444 (10)	0.0303 (9)	0.0246 (8)	0.0011 (8)	0.0026 (7)	0.0042 (7)
P1B	0.01821 (17)	0.01989 (19)	0.01877 (17)	0.00132 (14)	−0.00110 (14)	0.00191 (15)
F1B	0.0501 (7)	0.0230 (5)	0.0350 (6)	0.0149 (5)	−0.0044 (5)	−0.0020 (4)
F2B	0.0459 (6)	0.0337 (6)	0.0298 (5)	0.0048 (5)	−0.0009 (5)	−0.0123 (5)
F3B	0.0472 (6)	0.0488 (7)	0.0211 (5)	0.0075 (6)	−0.0113 (5)	−0.0007 (5)
F4B	0.0527 (7)	0.0335 (6)	0.0373 (6)	0.0189 (5)	−0.0123 (5)	0.0040 (5)
F5B	0.0453 (6)	0.0246 (5)	0.0312 (5)	0.0129 (5)	−0.0075 (5)	−0.0066 (4)
O1B	0.0232 (5)	0.0242 (6)	0.0272 (6)	0.0017 (5)	−0.0024 (4)	0.0063 (5)
O2B	0.0273 (6)	0.0310 (6)	0.0256 (6)	0.0014 (5)	0.0010 (5)	−0.0048 (5)
O3B	0.0195 (5)	0.0287 (6)	0.0267 (6)	−0.0026 (5)	−0.0010 (4)	0.0014 (5)
N1B	0.0181 (6)	0.0257 (7)	0.0240 (6)	0.0035 (5)	−0.0015 (5)	0.0072 (5)
N2B	0.0294 (7)	0.0189 (6)	0.0207 (6)	0.0028 (5)	−0.0054 (5)	0.0009 (5)
C1B	0.0184 (6)	0.0189 (7)	0.0207 (7)	−0.0009 (5)	0.0008 (5)	0.0032 (6)
C2B	0.0250 (7)	0.0185 (7)	0.0259 (7)	0.0022 (6)	0.0004 (6)	0.0010 (6)
C3B	0.0275 (7)	0.0241 (8)	0.0228 (7)	−0.0005 (6)	0.0023 (6)	−0.0042 (6)
C4B	0.0284 (8)	0.0307 (9)	0.0197 (7)	−0.0004 (7)	−0.0019 (6)	0.0023 (6)
C5B	0.0284 (8)	0.0225 (8)	0.0269 (8)	0.0051 (6)	−0.0032 (6)	0.0058 (6)
C6B	0.0262 (7)	0.0186 (7)	0.0235 (7)	0.0016 (6)	−0.0002 (6)	−0.0013 (6)
C7B	0.0237 (8)	0.0287 (9)	0.0402 (10)	−0.0012 (7)	0.0059 (7)	0.0052 (8)
C8B	0.0423 (10)	0.0317 (9)	0.0292 (9)	−0.0027 (8)	−0.0069 (8)	−0.0063 (8)

Geometric parameters (Å, º)

P1A—O1A	1.4690 (12)	P1B—O1B	1.4756 (12)
P1A—O2A	1.5712 (13)	P1B—O2B	1.5706 (12)
P1A—O3A	1.5562 (13)	P1B—O3B	1.5573 (12)
P1A—N1A	1.6452 (15)	P1B—N1B	1.6349 (14)
F1A—C2A	1.3444 (19)	F1B—C2B	1.3386 (19)
F2A—C3A	1.336 (2)	F2B—C3B	1.3413 (19)
F3A—C4A	1.3375 (19)	F3B—C4B	1.3415 (19)
F4A—C5A	1.338 (2)	F4B—C5B	1.3352 (19)
F5A—C6A	1.341 (2)	F5B—C6B	1.3462 (18)
O2A—C8A	1.449 (2)	O2B—C8B	1.449 (2)
O3A—C7A	1.432 (2)	O3B—C7B	1.448 (2)
N1A—N2A	1.4346 (19)	N1B—N2B	1.4040 (19)
N1A—H1A	0.79 (2)	N1B—H1B	0.83 (2)
N2A—C1A	1.408 (2)	N2B—C1B	1.384 (2)
N2A—H2A	0.88 (2)	N2B—H2B	0.82 (2)
C1A—C2A	1.390 (2)	C1B—C2B	1.395 (2)
C1A—C6A	1.392 (2)	C1B—C6B	1.397 (2)
C2A—C3A	1.383 (2)	C2B—C3B	1.386 (2)
C3A—C4A	1.375 (3)	C3B—C4B	1.379 (2)
C4A—C5A	1.380 (3)	C4B—C5B	1.370 (2)
C5A—C6A	1.382 (2)	C5B—C6B	1.375 (2)
C7A—H7AA	0.9800	C7B—H7BA	0.9800
C7A—H7AB	0.9800	C7B—H7BB	0.9800
C7A—H7AC	0.9800	C7B—H7BC	0.9800
C8A—H8AA	0.9800	C8B—H8BA	0.9800
C8A—H8AB	0.9800	C8B—H8BB	0.9800
C8A—H8AC	0.9800	C8B—H8BC	0.9800
O1A—P1A—O2A	114.89 (7)	O1B—P1B—O2B	113.61 (7)
O1A—P1A—O3A	111.68 (8)	O1B—P1B—O3B	116.81 (7)
O1A—P1A—N1A	108.59 (7)	O1B—P1B—N1B	109.81 (7)
O2A—P1A—N1A	110.17 (7)	O2B—P1B—N1B	111.06 (7)
O3A—P1A—O2A	102.93 (7)	O3B—P1B—O2B	102.05 (6)
O3A—P1A—N1A	108.34 (7)	O3B—P1B—N1B	102.82 (7)
C8A—O2A—P1A	118.35 (11)	C8B—O2B—P1B	118.48 (11)
C7A—O3A—P1A	125.59 (13)	C7B—O3B—P1B	121.41 (11)
P1A—N1A—H1A	113.5 (15)	P1B—N1B—H1B	116.8 (15)
N2A—N1A—P1A	116.49 (10)	N2B—N1B—P1B	116.23 (11)
N2A—N1A—H1A	115.7 (16)	N2B—N1B—H1B	115.0 (16)
N1A—N2A—H2A	107.5 (13)	N1B—N2B—H2B	114.7 (17)
C1A—N2A—N1A	112.66 (12)	C1B—N2B—N1B	119.57 (13)
C1A—N2A—H2A	112.2 (14)	C1B—N2B—H2B	115.5 (17)
C2A—C1A—N2A	121.89 (14)	N2B—C1B—C2B	127.74 (14)
C2A—C1A—C6A	116.19 (14)	N2B—C1B—C6B	116.62 (14)
C6A—C1A—N2A	121.89 (15)	C2B—C1B—C6B	115.57 (14)
F1A—C2A—C1A	119.20 (14)	F1B—C2B—C1B	122.31 (14)
F1A—C2A—C3A	118.22 (15)	F1B—C2B—C3B	116.64 (15)
C3A—C2A—C1A	122.56 (15)	C3B—C2B—C1B	121.05 (15)
F2A—C3A—C2A	120.10 (15)	F2B—C3B—C2B	119.13 (15)
F2A—C3A—C4A	120.19 (15)	F2B—C3B—C4B	119.49 (15)
C4A—C3A—C2A	119.68 (16)	C4B—C3B—C2B	121.38 (15)
F3A—C4A—C3A	120.02 (17)	F3B—C4B—C3B	120.27 (16)
F3A—C4A—C5A	120.46 (16)	F3B—C4B—C5B	120.87 (16)
C3A—C4A—C5A	119.49 (15)	C5B—C4B—C3B	118.84 (15)
F4A—C5A—C4A	120.32 (15)	F4B—C5B—C4B	120.23 (15)
F4A—C5A—C6A	119.63 (16)	F4B—C5B—C6B	120.18 (16)
C4A—C5A—C6A	120.05 (16)	C4B—C5B—C6B	119.59 (15)
F5A—C6A—C1A	120.37 (14)	F5B—C6B—C1B	117.88 (14)
F5A—C6A—C5A	117.61 (15)	F5B—C6B—C5B	118.57 (14)
C5A—C6A—C1A	122.03 (16)	C5B—C6B—C1B	123.55 (15)
O3A—C7A—H7AA	109.5	O3B—C7B—H7BA	109.5
O3A—C7A—H7AB	109.5	O3B—C7B—H7BB	109.5
O3A—C7A—H7AC	109.5	O3B—C7B—H7BC	109.5
H7AA—C7A—H7AB	109.5	H7BA—C7B—H7BB	109.5
H7AA—C7A—H7AC	109.5	H7BA—C7B—H7BC	109.5
H7AB—C7A—H7AC	109.5	H7BB—C7B—H7BC	109.5
O2A—C8A—H8AA	109.5	O2B—C8B—H8BA	109.5
O2A—C8A—H8AB	109.5	O2B—C8B—H8BB	109.5
O2A—C8A—H8AC	109.5	O2B—C8B—H8BC	109.5
H8AA—C8A—H8AB	109.5	H8BA—C8B—H8BB	109.5
H8AA—C8A—H8AC	109.5	H8BA—C8B—H8BC	109.5
H8AB—C8A—H8AC	109.5	H8BB—C8B—H8BC	109.5
P1A—N1A—N2A—C1A	138.22 (12)	P1B—N1B—N2B—C1B	−123.74 (14)
F1A—C2A—C3A—F2A	−1.1 (2)	F1B—C2B—C3B—F2B	−0.4 (2)
F1A—C2A—C3A—C4A	−179.12 (15)	F1B—C2B—C3B—C4B	178.92 (15)
F2A—C3A—C4A—F3A	−0.1 (3)	F2B—C3B—C4B—F3B	1.4 (2)
F2A—C3A—C4A—C5A	−178.18 (16)	F2B—C3B—C4B—C5B	179.91 (15)
F3A—C4A—C5A—F4A	1.4 (3)	F3B—C4B—C5B—F4B	−0.4 (3)
F3A—C4A—C5A—C6A	−178.03 (16)	F3B—C4B—C5B—C6B	179.38 (16)
F4A—C5A—C6A—F5A	1.1 (2)	F4B—C5B—C6B—F5B	−1.8 (2)
F4A—C5A—C6A—C1A	−179.01 (15)	F4B—C5B—C6B—C1B	178.31 (15)
O1A—P1A—O2A—C8A	−42.82 (15)	O1B—P1B—O2B—C8B	47.26 (15)
O1A—P1A—O3A—C7A	−158.36 (15)	O1B—P1B—O3B—C7B	67.71 (14)
O1A—P1A—N1A—N2A	174.10 (11)	O1B—P1B—N1B—N2B	−173.23 (11)
O2A—P1A—O3A—C7A	−34.58 (17)	O2B—P1B—O3B—C7B	−56.81 (14)
O2A—P1A—N1A—N2A	47.47 (12)	O2B—P1B—N1B—N2B	−46.73 (14)
O3A—P1A—O2A—C8A	−164.45 (13)	O3B—P1B—O2B—C8B	173.90 (13)
O3A—P1A—N1A—N2A	−64.43 (13)	O3B—P1B—N1B—N2B	61.76 (13)
N1A—P1A—O2A—C8A	80.19 (13)	N1B—P1B—O2B—C8B	−77.12 (14)
N1A—P1A—O3A—C7A	82.10 (17)	N1B—P1B—O3B—C7B	−171.99 (13)
N1A—N2A—C1A—C2A	119.18 (16)	N1B—N2B—C1B—C2B	7.1 (2)
N1A—N2A—C1A—C6A	−63.17 (19)	N1B—N2B—C1B—C6B	−176.00 (14)
N2A—C1A—C2A—F1A	−2.7 (2)	N2B—C1B—C2B—F1B	−2.6 (3)
N2A—C1A—C2A—C3A	178.46 (15)	N2B—C1B—C2B—C3B	177.79 (15)
N2A—C1A—C6A—F5A	1.4 (2)	N2B—C1B—C6B—F5B	3.4 (2)
N2A—C1A—C6A—C5A	−178.52 (15)	N2B—C1B—C6B—C5B	−176.71 (15)
C1A—C2A—C3A—F2A	177.80 (15)	C1B—C2B—C3B—F2B	179.18 (14)
C1A—C2A—C3A—C4A	−0.3 (3)	C1B—C2B—C3B—C4B	−1.5 (2)
C2A—C1A—C6A—F5A	179.15 (15)	C2B—C1B—C6B—F5B	−179.36 (14)
C2A—C1A—C6A—C5A	−0.7 (2)	C2B—C1B—C6B—C5B	0.5 (2)
C2A—C3A—C4A—F3A	177.98 (16)	C2B—C3B—C4B—F3B	−177.98 (15)
C2A—C3A—C4A—C5A	−0.1 (3)	C2B—C3B—C4B—C5B	0.6 (3)
C3A—C4A—C5A—F4A	179.46 (16)	C3B—C4B—C5B—F4B	−178.90 (15)
C3A—C4A—C5A—C6A	0.1 (3)	C3B—C4B—C5B—C6B	0.8 (3)
C4A—C5A—C6A—F5A	−179.50 (16)	C4B—C5B—C6B—F5B	178.47 (15)
C4A—C5A—C6A—C1A	0.4 (3)	C4B—C5B—C6B—C1B	−1.4 (3)
C6A—C1A—C2A—F1A	179.51 (14)	C6B—C1B—C2B—F1B	−179.53 (14)
C6A—C1A—C2A—C3A	0.7 (2)	C6B—C1B—C2B—C3B	0.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7AB···F5A	0.98	2.49	3.121 (2)	122
C7A—H7AC···O2A^i	0.98	2.77	3.459 (2)	128
C8A—H8AB···O1B^ii	0.98	2.80	3.452 (2)	124
C7B—H7BB···F4A^iii	0.98	2.81	3.411 (2)	120
N2A—H2A···O1B^ii	0.88 (2)	2.06 (2)	2.9308 (18)	167.3 (19)
N1A—H1A···O1A^iv	0.79 (2)	2.14 (2)	2.9238 (18)	169 (2)
N1B—H1B···O1B^v	0.83 (2)	2.07 (2)	2.8942 (18)	170 (2)
N2B—H2B···O1A	0.82 (2)	2.08 (2)	2.8774 (19)	167 (2)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+1/2, y−1/2, −z+3/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y, −z+1.