(Z)-1,2-Diphenyl-2-(phenyl­hydrazono)ethanone

The title compound, C₂₀H₁₆N₂O, obtained from the reaction of benzil with phenyl­hydrazine, crystallizes with two crystallographically independent and conformationally different mol­ecules in the asymmetric unit. The dihedral angle between the two phenyl rings of the benzil unit is 15.04 (6)° in one mol­ecule and 68.81 (5)° in the other. The crystal structure is stabilized by N—H...O and C—H...O inter­molecular hydrogen bonds and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.107
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) .        200 Ang.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.54 Ratio
PLAT420_ALERT_2_C D-H Without Acceptor       N4B    -   H4B    ...          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: Bouacida and Benard-Rocherulle: Structure determination and preparation of paper.

 Bendaas, Yahiaoui and  Bouchama:Organic synthesis.

 Djedouani:crystallization and preparation of paper.


   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia,1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

(Z)-1,2-Diphenyl-2-(phenylhydrazono)ethanone

Crystal data

C20H16N2O	Z = 4
Mr = 300.35	F(000) = 632
Triclinic, P1	Dx = 1.254 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.739 (2) Å	Cell parameters from 9755 reflections
b = 12.107 (2) Å	θ = 2.3–25.8°
c = 12.521 (2) Å	µ = 0.08 mm^−1
α = 107.199 (7)°	T = 295 K
β = 94.809 (8)°	Needle, yellow
γ = 107.535 (7)°	0.26 × 0.22 × 0.15 mm
V = 1591.5 (5) Å^3

Data collection

Bruker SMART APEX II CCD area-detector diffractometer	5015 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Detector resolution: 8.33 pixels mm^-1	θmax = 27.6°, θmin = 1.7°
ω scans	h = −15→15
30595 measured reflections	k = −14→15
7219 independent reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0293P)^2 + 1.3984P] where P = (Fo^2 + 2Fc^2)/3
7219 reflections	(Δ/σ)max = 0.003
421 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix·B The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1A	0.32833 (8)	0.63820 (8)	0.72129 (10)	0.0699 (4)
N3A	0.14680 (9)	0.34306 (9)	0.68771 (9)	0.0416 (3)
N4A	0.14611 (10)	0.22852 (9)	0.66417 (10)	0.0467 (3)
C1A	0.23573 (11)	0.55069 (11)	0.70723 (11)	0.0469 (4)
C2A	0.23765 (11)	0.42405 (11)	0.66883 (10)	0.0428 (4)
C5A	0.06019 (10)	0.14437 (10)	0.69874 (10)	0.0393 (4)
C6A	−0.01919 (11)	0.17833 (12)	0.76641 (11)	0.0467 (4)
C7A	−0.10031 (13)	0.09146 (14)	0.79912 (13)	0.0590 (5)
C8A	−0.10347 (13)	−0.02845 (14)	0.76588 (15)	0.0658 (6)
C9A	−0.02471 (13)	−0.06176 (13)	0.69811 (14)	0.0640 (5)
C10A	0.05674 (12)	0.02373 (12)	0.66414 (12)	0.0530 (5)
C11A	0.34123 (11)	0.39704 (12)	0.61948 (11)	0.0475 (4)
C12A	0.32123 (16)	0.32144 (17)	0.50763 (14)	0.0744 (6)
C13A	0.4157 (2)	0.2931 (2)	0.46119 (18)	0.0999 (10)
C14A	0.5302 (2)	0.3395 (2)	0.5259 (2)	0.0996 (10)
C15A	0.55088 (15)	0.41319 (18)	0.6373 (2)	0.0842 (8)
C16A	0.45700 (12)	0.44237 (13)	0.68421 (14)	0.0604 (5)
C17A	0.11971 (12)	0.57326 (11)	0.72892 (11)	0.0461 (4)
C18A	0.01264 (12)	0.50894 (12)	0.64947 (12)	0.0530 (5)
C19A	−0.08982 (14)	0.54074 (15)	0.66338 (17)	0.0738 (6)
C20A	−0.08813 (18)	0.63377 (17)	0.7576 (2)	0.0889 (9)
C21A	0.0164 (2)	0.69663 (16)	0.83897 (17)	0.0877 (8)
C22A	0.12097 (16)	0.66773 (13)	0.82452 (13)	0.0664 (5)
O1B	0.61556 (8)	0.77022 (8)	0.21147 (9)	0.0600 (3)
N3B	0.46500 (9)	0.95645 (9)	0.16164 (9)	0.0439 (3)
N4B	0.47072 (10)	1.07244 (10)	0.18073 (10)	0.0496 (3)
C1N	0.52827 (11)	0.79916 (11)	0.18786 (11)	0.0438 (4)
C2B	0.53815 (11)	0.93040 (11)	0.22604 (10)	0.0420 (4)
C5B	0.38925 (10)	1.09862 (11)	0.11195 (10)	0.0398 (4)
C6B	0.30667 (12)	1.00735 (12)	0.01913 (11)	0.0511 (4)
C7B	0.22605 (13)	1.03739 (15)	−0.04356 (12)	0.0636 (5)
C8B	0.22631 (13)	1.15643 (16)	−0.01547 (13)	0.0623 (6)
C9B	0.30973 (12)	1.24681 (13)	0.07571 (13)	0.0546 (5)
C10B	0.39126 (11)	1.21874 (11)	0.13969 (11)	0.0471 (4)
C11B	0.63040 (11)	1.01736 (11)	0.32850 (10)	0.0419 (4)
C12B	0.63178 (13)	0.98978 (13)	0.42888 (12)	0.0559 (5)
C13B	0.71440 (15)	1.06908 (15)	0.52632 (13)	0.0679 (6)
C14B	0.79653 (14)	1.17724 (14)	0.52546 (13)	0.0655 (5)
C15B	0.79727 (12)	1.20531 (12)	0.42735 (12)	0.0562 (5)
C16B	0.71517 (11)	1.12575 (11)	0.32879 (11)	0.0461 (4)
C17B	0.41068 (11)	0.70165 (10)	0.12072 (10)	0.0419 (4)
C18B	0.41346 (13)	0.60251 (12)	0.03179 (11)	0.0511 (4)
C19B	0.30829 (14)	0.50480 (13)	−0.02457 (12)	0.0581 (5)
C20B	0.20017 (14)	0.50375 (13)	0.00921 (14)	0.0654 (5)
C21B	0.19603 (13)	0.60068 (14)	0.09782 (15)	0.0688 (6)
C22B	0.30056 (12)	0.70066 (12)	0.15260 (12)	0.0559 (5)
H4A	0.2082 (12)	0.2093 (12)	0.6461 (11)	0.0500*
H6A	−0.01781	0.25921	0.78965	0.0560*
H7A	−0.15383	0.11431	0.84445	0.0707*
H8A	−0.15814	−0.08628	0.78891	0.0789*
H9A	−0.02643	−0.14276	0.67500	0.0768*
H10A	0.10935	0.00027	0.61796	0.0636*
H12A	0.24353	0.28946	0.46333	0.0893*
H13A	0.40154	0.24235	0.38581	0.1199*
H14A	0.59399	0.32105	0.49436	0.1195*
H15A	0.62852	0.44369	0.68148	0.1010*
H16A	0.47176	0.49279	0.75977	0.0725*
H18A	0.00985	0.44364	0.58609	0.0636*
H19A	−0.16041	0.49852	0.60823	0.0885*
H20A	−0.15756	0.65472	0.76683	0.1067*
H21A	0.01686	0.75885	0.90404	0.1053*
H22A	0.19192	0.71174	0.87897	0.0797*
H4B	0.5240 (12)	1.1349 (13)	0.2341 (11)	0.0500*
H6B	0.30569	0.92669	−0.00064	0.0613*
H7B	0.17046	0.97628	−0.10592	0.0764*
H8B	0.17063	1.17540	−0.05777	0.0747*
H9B	0.31122	1.32758	0.09443	0.0656*
H10B	0.44745	1.28037	0.20132	0.0565*
H12B	0.57631	0.91701	0.43016	0.0671*
H13B	0.71465	1.04948	0.59275	0.0815*
H14B	0.85151	1.23123	0.59155	0.0786*
H15B	0.85320	1.27820	0.42683	0.0674*
H16B	0.71691	1.14518	0.26228	0.0553*
H18B	0.48709	0.60186	0.00988	0.0613*
H19B	0.31083	0.43975	−0.08543	0.0697*
H20B	0.12943	0.43726	−0.02792	0.0784*
H21B	0.12258	0.59914	0.12117	0.0825*
H22B	0.29672	0.76727	0.21093	0.0671*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0466 (5)	0.0405 (5)	0.1117 (9)	0.0026 (4)	−0.0001 (5)	0.0269 (5)
N3A	0.0404 (5)	0.0335 (5)	0.0503 (6)	0.0116 (4)	0.0036 (4)	0.0156 (4)
N4A	0.0410 (6)	0.0371 (5)	0.0695 (7)	0.0174 (4)	0.0176 (5)	0.0226 (5)
C1A	0.0446 (7)	0.0377 (6)	0.0535 (7)	0.0071 (5)	−0.0011 (6)	0.0183 (5)
C2A	0.0388 (6)	0.0386 (6)	0.0492 (7)	0.0092 (5)	0.0024 (5)	0.0182 (5)
C5A	0.0332 (6)	0.0376 (6)	0.0487 (7)	0.0113 (5)	0.0035 (5)	0.0188 (5)
C6A	0.0460 (7)	0.0461 (7)	0.0514 (7)	0.0186 (5)	0.0082 (6)	0.0187 (6)
C7A	0.0500 (8)	0.0719 (10)	0.0680 (9)	0.0238 (7)	0.0214 (7)	0.0364 (8)
C8A	0.0514 (8)	0.0634 (10)	0.0913 (11)	0.0104 (7)	0.0174 (8)	0.0470 (9)
C9A	0.0590 (9)	0.0417 (8)	0.0951 (11)	0.0143 (6)	0.0143 (8)	0.0316 (8)
C10A	0.0498 (8)	0.0422 (7)	0.0731 (9)	0.0190 (6)	0.0166 (7)	0.0236 (6)
C11A	0.0463 (7)	0.0448 (7)	0.0586 (8)	0.0135 (5)	0.0144 (6)	0.0288 (6)
C12A	0.0761 (11)	0.0914 (12)	0.0606 (10)	0.0333 (9)	0.0189 (8)	0.0262 (9)
C13A	0.1184 (18)	0.1229 (18)	0.0829 (14)	0.0609 (15)	0.0552 (14)	0.0398 (12)
C14A	0.0893 (15)	0.1164 (17)	0.139 (2)	0.0567 (13)	0.0745 (15)	0.0723 (16)
C15A	0.0495 (9)	0.0882 (13)	0.1340 (18)	0.0234 (9)	0.0320 (10)	0.0610 (13)
C16A	0.0448 (8)	0.0565 (8)	0.0828 (10)	0.0121 (6)	0.0134 (7)	0.0325 (8)
C17A	0.0529 (8)	0.0328 (6)	0.0535 (7)	0.0116 (5)	0.0117 (6)	0.0188 (5)
C18A	0.0469 (8)	0.0450 (7)	0.0664 (9)	0.0154 (6)	0.0111 (6)	0.0179 (6)
C19A	0.0507 (9)	0.0662 (10)	0.1116 (14)	0.0227 (7)	0.0224 (9)	0.0356 (10)
C20A	0.0825 (13)	0.0660 (11)	0.1444 (19)	0.0383 (10)	0.0644 (14)	0.0479 (12)
C21A	0.1249 (17)	0.0498 (10)	0.1001 (14)	0.0361 (10)	0.0658 (14)	0.0234 (9)
C22A	0.0889 (11)	0.0407 (8)	0.0626 (9)	0.0149 (7)	0.0190 (8)	0.0137 (6)
O1B	0.0471 (5)	0.0495 (5)	0.0870 (7)	0.0214 (4)	0.0042 (5)	0.0254 (5)
N3B	0.0458 (6)	0.0353 (5)	0.0500 (6)	0.0139 (4)	0.0042 (5)	0.0150 (4)
N4B	0.0509 (6)	0.0333 (5)	0.0572 (7)	0.0127 (4)	−0.0087 (5)	0.0118 (5)
C1N	0.0424 (7)	0.0409 (7)	0.0528 (7)	0.0159 (5)	0.0093 (6)	0.0210 (5)
C2B	0.0397 (6)	0.0373 (6)	0.0491 (7)	0.0122 (5)	0.0055 (5)	0.0167 (5)
C5B	0.0357 (6)	0.0420 (6)	0.0448 (7)	0.0122 (5)	0.0069 (5)	0.0204 (5)
C6B	0.0542 (8)	0.0480 (7)	0.0463 (7)	0.0153 (6)	0.0023 (6)	0.0133 (6)
C7B	0.0586 (9)	0.0758 (10)	0.0484 (8)	0.0190 (7)	−0.0059 (7)	0.0179 (7)
C8B	0.0564 (9)	0.0872 (11)	0.0609 (9)	0.0345 (8)	0.0074 (7)	0.0411 (8)
C9B	0.0541 (8)	0.0566 (8)	0.0701 (9)	0.0264 (7)	0.0170 (7)	0.0365 (7)
C10B	0.0414 (7)	0.0418 (7)	0.0580 (8)	0.0107 (5)	0.0057 (6)	0.0215 (6)
C11B	0.0411 (7)	0.0396 (6)	0.0471 (7)	0.0167 (5)B	0.0054 (5)	0.0156 (5)
C12B	0.0571 (8)	0.0553 (8)	0.0563 (8)	0.0144 (6)	0.0098 (7)	0.0256 (7)
C13B	0.0827 (11)	0.0753 (11)	0.0462 (8)	0.0267 (9)	0.0037 (7)	0.0238 (7)
C14B	0.0730 (10)	0.0541 (9)	0.0555 (9)	0.0197 (7)	−0.0120 (7)	0.0075 (7)
C15B	0.0544 (8)	0.0388 (7)	0.0661 (9)	0.0118 (6)	−0.0062 (7)	0.0136 (6)
C16B	0.0482 (7)	0.0393 (7)	0.0513 (7)	0.0154 (5)	0.0033 (6)	0.0174 (5)
C17B	0.0451 (7)	0.0350 (6)	0.0488 (7)	0.0156 (5)	0.0069 (5)	0.0175 (5)
C18B	0.0586 (8)	0.0451 (7)	0.0542 (8)	0.0208 (6)	0.0161 (6)	0.0189 (6)
C19B	0.0756 (10)	0.0430 (7)	0.0495 (8)	0.0194 (7)	0.0026 (7)	0.0103 (6)
C20B	0.0569 (9)	0.0466 (8)	0.0761 (10)	0.0080 (6)	−0.0115 (8)	0.0138 (7)
C21B	0.0444 (8)	0.0579 (9)	0.0963 (12)	0.0167 (7)	0.0096 (8)	0.0169 (8)
C22B	0.0494 (8)	0.0453 (7)	0.0677 (9)	0.0191 (6)	0.0095 (7)	0.0090 (6)

Geometric parameters (Å, º)

O1A—C1A	1.2242 (17)	C18A—H18A	0.93
O1B—C1N	1.2194 (17)	C19A—H19A	0.93
N3A—N4A	1.3271 (16)	C20A—H20A	0.93
N3A—C2A	1.3054 (18)	C21A—H21A	0.93
N4A—C5A	1.3991 (17)	C22A—H22A	0.93
N4A—H4A	0.858 (15)	C1N—C17B	1.4975 (19)
N3B—C2B	1.2979 (17)	C1N—C2B	1.4823 (19)
N3B—N4B	1.3325 (17)	C2B—C11B	1.4860 (18)
N4B—C5B	1.4010 (18)	C5B—C10B	1.3840 (19)
N4B—H4B	0.869 (14)	C5B—C6B	1.3848 (18)
C1A—C2A	1.4728 (19)	C6B—C7B	1.377 (2)
C1A—C17A	1.499 (2)	C7B—C8B	1.378 (3)
C2A—C11A	1.4877 (19)	C8B—C9B	1.374 (2)
C5A—C6A	1.3829 (18)	C9B—C10B	1.379 (2)
C5A—C10A	1.3820 (19)	C11B—C12B	1.3927 (19)
C6A—C7A	1.377 (2)	C11B—C16B	1.3864 (19)
C7A—C8A	1.375 (2)	C12B—C13B	1.378 (2)
C8A—C9A	1.375 (2)	C13B—C14B	1.376 (3)
C9A—C10A	1.378 (2)	C14B—C15B	1.368 (2)
C11A—C12A	1.383 (2)	C15B—C16B	1.385 (2)
C11A—C16A	1.381 (2)	C17B—C22B	1.382 (2)
C12A—C13A	1.380 (3)	C17B—C18B	1.3860 (19)
C13A—C14A	1.368 (3)	C18B—C19B	1.379 (2)
C14A—C15A	1.370 (3)	C19B—C20B	1.369 (2)
C15A—C16A	1.380 (3)	C20B—C21B	1.373 (2)
C17A—C18A	1.385 (2)	C21B—C22B	1.384 (2)
C17A—C22A	1.385 (2)	C6B—H6B	0.93
C18A—C19A	1.378 (2)	C7B—H7B	0.93
C19A—C20A	1.363 (3)	C8B—H8B	0.93
C20A—C21A	1.376 (3)	C9B—H9B	0.93
C21A—C22A	1.386 (3)	C10B—H10B	0.93
C6A—H6A	0.93	C12B—H12B	0.93
C7A—H7A	0.93	C13B—H13B	0.93
C8A—H8A	0.93	C14B—H14B	0.93
C9A—H9A	0.93	C15B—H15B	0.93
C10A—H10A	0.93	C16B—H16B	0.93
C12A—H12A	0.93	C18B—H18B	0.93
C13A—H13A	0.93	C19B—H19B	0.93
C14A—H14A	0.93	C20B—H20B	0.93
C15A—H15A	0.93	C21B—H21B	0.93
C16A—H16A	0.93	C22B—H22B	0.93
O1A···C16A	3.1214 (19)	C19B···H9B^xii	2.9600
O1A···C16B^i	3.2721 (18)	C20A···H9A^x	3.0800
O1A···C10B^i	3.2690 (18)	C22A···H16B^i	3.0200
O1B···C12B	3.1371 (19)	H4A···C12A	2.702 (14)
O1B···C16A^ii	3.148 (2)	H4A···H10A	2.3500
O1B···N4A^ii	3.0793 (17)	H4A···C11A	2.472 (15)
O1B···C8B^iii	3.364 (2)	H4A···O1B^ii	2.517 (14)
O1A···H22A	2.7600	H4B···C16B	2.497 (15)
O1A···H4B^i	2.631 (16)	H4B···H10B	2.3200
O1A···H10B^i	2.5100	H4B···C11B	2.608 (15)
O1A···H16A	2.8800	H4B···O1A^i	2.631 (16)
O1A···H16B^i	2.7800	H4B···H16B	2.2200
O1B···H4A^ii	2.517 (14)	H6A···H21B^viii	2.4600
O1B···H18B	2.7000	H6A···N3A	2.5300
N3A···C18A	3.0151 (19)	H6B···H22A^xiii	2.4700
N3B···C22B	3.0795 (19)	H6B···N3B	2.5100
N4A···C12A	3.150 (2)	H7A···C6B^viii	2.9500
N4A···O1B^ii	3.0793 (17)	H7B···C9A^xiv	3.0400
N4B···C16B	3.0614 (19)	H8A···C10B^viii	3.0800
N3A···H6A	2.5300	H8A···C5B^viii	3.0600
N3A···H18A	2.7300	H8B···C6A^xiv	3.0100
N3B···H6B	2.5100	H8B···C5A^xiv	3.0800
N3B···H22B	2.8000	H9A···C20A^xii	3.0800
N4B···H16B	2.7600	H9B···C19B^x	2.9600
C6A···C14B^iv	3.556 (2)	H10A···H4A	2.3500
C8B···O1B^iii	3.364 (2)	H10A···C13B^ii	3.0000
C10B···O1A^i	3.2690 (18)	H10A···C14B^ii	2.9200
C12A···N4A	3.150 (2)	H10A···C15B^ii	2.9400
C12B···O1B	3.1371 (19)	H10A···C16B^ii	3.0500
C14B···C6A^v	3.556 (2)	H10B···H16A^i	2.5000
C16A···O1B^ii	3.148 (2)	H10B···H13A^x	2.5500
C16A···O1A	3.1214 (19)	H10B···O1A^i	2.5100
C16B···O1A^i	3.2721 (18)	H10B···H4B	2.3200
C16B···N4B	3.0614 (19)	H10B···C16A^i	3.0300
C18A···N3A	3.0151 (19)	H12B···C1N	2.8700
C22B···N3B	3.0795 (19)	H13A···C10B^xii	3.0000
C1N···H12B	2.8700	H13A···H10B^xii	2.5500
C2A···H18A	2.8900	H13B···C7A^v	3.0400
C2A···H19B^vi	3.0600	H14B···C6A^v	2.8900
C2B···H22B	2.8800	H15B···C18A^i	3.0500
C5A···H8B^vii	3.0800	H15B···H18A^v	2.4800
C5B···H8A^viii	3.0600	H15B···C17A^i	3.0000
C6A···H14B^iv	2.8900	H16A···O1A	2.8800
C6A···H8B^vii	3.0100	H16A···H10B^i	2.5000
C6B···H7A^viii	2.9500	H16B···O1A^i	2.7800
C7A···H13B^iv	3.0400	H16B···H4B	2.2200
C9A···H7B^vii	3.0400	H16B···C22A^i	3.0200
C9B···H20A^ix	3.0000	H16B···N4B	2.7600
C9B···H18B^iii	3.0300	H18A···H15B^iv	2.4800
C10B···H13A^x	3.0000	H18A···C2A	2.8900
C10B···H8A^viii	3.0800	H18A···N3A	2.7300
C11A···H4A	2.472 (15)	H18B···C9B^iii	3.0300
C11B···H4B	2.608 (15)	H18B···O1B	2.7000
C12A···H4A	2.702 (14)	H18B···C18B^xi	2.9700
C13B···H10A^ii	3.0000	H18B···C19B^xi	3.0700
C14B···H10A^ii	2.9200	H18B···H18B^xi	2.5200
C15B···H10A^ii	2.9400	H19B···C2A^xiii	3.0600
C16A···H10B^i	3.0300	H20A···C9B^ix	3.0000
C16B···H10A^ii	3.0500	H21B···H6A^viii	2.4600
C16B···H4B	2.497 (15)	H22A···H6B^vi	2.4700
C17A···H15B^i	3.0000	H22A···O1A	2.7600
C18A···H15B^i	3.0500	H22B···N3B	2.8000
C18B···H18B^xi	2.9700	H22B···C2B	2.8800
C19B···H18B^xi	3.0700
N4A—N3A—C2A	118.86 (11)	C22A—C21A—H21A	120.00
N3A—N4A—C5A	120.19 (11)	C20A—C21A—H21A	120.00
C5A—N4A—H4A	116.1 (10)	C17A—C22A—H22A	120.00
N3A—N4A—H4A	121.4 (10)	C21A—C22A—H22A	120.00
N4B—N3B—C2B	120.73 (11)	C2B—C1N—C17B	120.02 (11)
N3B—N4B—C5B	119.97 (11)	O1B—C1N—C2B	120.16 (12)
N3B—N4B—H4B	123.3 (10)	O1B—C1N—C17B	119.82 (12)
C5B—N4B—H4B	116.7 (10)	N3B—C2B—C11B	127.19 (12)
O1A—C1A—C2A	120.52 (12)	N3B—C2B—C1N	114.33 (11)
O1A—C1A—C17A	119.45 (12)	C1N—C2B—C11B	118.44 (11)
C2A—C1A—C17A	120.03 (12)	N4B—C5B—C10B	118.44 (11)
N3A—C2A—C11A	124.63 (12)	N4B—C5B—C6B	121.59 (12)
C1A—C2A—C11A	120.54 (12)	C6B—C5B—C10B	119.96 (12)
N3A—C2A—C1A	114.72 (12)	C5B—C6B—C7B	119.24 (14)
N4A—C5A—C10A	117.96 (12)	C6B—C7B—C8B	121.13 (14)
N4A—C5A—C6A	122.33 (12)	C7B—C8B—C9B	119.28 (15)
C6A—C5A—C10A	119.71 (12)	C8B—C9B—C10B	120.54 (15)
C5A—C6A—C7A	119.50 (13)	C5B—C10B—C9B	119.83 (13)
C6A—C7A—C8A	121.09 (15)	C2B—C11B—C12B	118.95 (12)
C7A—C8A—C9A	119.12 (16)	C12B—C11B—C16B	118.32 (12)
C8A—C9A—C10A	120.63 (15)	C2B—C11B—C16B	122.73 (11)
C5A—C10A—C9A	119.95 (13)	C11B—C12B—C13B	120.75 (15)
C2A—C11A—C12A	119.71 (13)	C12B—C13B—C14B	120.09 (15)
C2A—C11A—C16A	121.43 (12)	C13B—C14B—C15B	119.97 (15)
C12A—C11A—C16A	118.83 (14)	C14B—C15B—C16B	120.35 (14)
C11A—C12A—C13A	120.51 (17)	C11B—C16B—C15B	120.51 (12)
C12A—C13A—C14A	120.1 (2)	C1N—C17B—C18B	119.02 (12)
C13A—C14A—C15A	120.0 (2)	C18B—C17B—C22B	118.83 (13)
C14A—C15A—C16A	120.28 (19)	C1N—C17B—C22B	121.77 (11)
C11A—C16A—C15A	120.32 (16)	C17B—C18B—C19B	120.75 (14)
C1A—C17A—C18A	121.06 (12)	C18B—C19B—C20B	119.88 (14)
C18A—C17A—C22A	118.80 (14)	C19B—C20B—C21B	120.09 (15)
C1A—C17A—C22A	119.86 (13)	C20B—C21B—C22B	120.34 (15)
C17A—C18A—C19A	120.67 (14)	C17B—C22B—C21B	120.07 (13)
C18A—C19A—C20A	120.29 (18)	C5B—C6B—H6B	120.00
C19A—C20A—C21A	119.9 (2)	C7B—C6B—H6B	120.00
C20A—C21A—C22A	120.36 (19)	C6B—C7B—H7B	119.00
C17A—C22A—C21A	119.94 (16)	C8B—C7B—H7B	119.00
C5A—C6A—H6A	120.00	C7B—C8B—H8B	120.00
C7A—C6A—H6A	120.00	C9B—C8B—H8B	120.00
C6A—C7A—H7A	119.00	C8B—C9B—H9B	120.00
C8A—C7A—H7A	119.00	C10B—C9B—H9B	120.00
C9A—C8A—H8A	120.00	C5B—C10B—H10B	120.00
C7A—C8A—H8A	120.00	C9B—C10B—H10B	120.00
C8A—C9A—H9A	120.00	C11B—C12B—H12B	120.00
C10A—C9A—H9A	120.00	C13B—C12B—H12B	120.00
C5A—C10A—H10A	120.00	C12B—C13B—H13B	120.00
C9A—C10A—H10A	120.00	C14B—C13B—H13B	120.00
C11A—C12A—H12A	120.00	C13B—C14B—H14B	120.00
C13A—C12A—H12A	120.00	C15B—C14B—H14B	120.00
C14A—C13A—H13A	120.00	C14B—C15B—H15B	120.00
C12A—C13A—H13A	120.00	C16B—C15B—H15B	120.00
C13A—C14A—H14A	120.00	C11B—C16B—H16B	120.00
C15A—C14A—H14A	120.00	C15B—C16B—H16B	120.00
C16A—C15A—H15A	120.00	C17B—C18B—H18B	120.00
C14A—C15A—H15A	120.00	C19B—C18B—H18B	120.00
C11A—C16A—H16A	120.00	C18B—C19B—H19B	120.00
C15A—C16A—H16A	120.00	C20B—C19B—H19B	120.00
C19A—C18A—H18A	120.00	C19B—C20B—H20B	120.00
C17A—C18A—H18A	120.00	C21B—C20B—H20B	120.00
C18A—C19A—H19A	120.00	C20B—C21B—H21B	120.00
C20A—C19A—H19A	120.00	C22B—C21B—H21B	120.00
C19A—C20A—H20A	120.00	C17B—C22B—H22B	120.00
C21A—C20A—H20A	120.00	C21B—C22B—H22B	120.00
C2A—N3A—N4A—C5A	170.55 (11)	C22A—C17A—C18A—C19A	2.0 (2)
N4A—N3A—C2A—C1A	−174.73 (11)	C17A—C18A—C19A—C20A	−2.0 (3)
N4A—N3A—C2A—C11A	1.53 (19)	C18A—C19A—C20A—C21A	0.3 (3)
N3A—N4A—C5A—C6A	−5.89 (19)	C19A—C20A—C21A—C22A	1.4 (3)
N3A—N4A—C5A—C10A	174.77 (12)	C20A—C21A—C22A—C17A	−1.4 (3)
N4B—N3B—C2B—C11B	3.1 (2)	O1B—C1N—C2B—N3B	152.88 (13)
C2B—N3B—N4B—C5B	−178.57 (12)	O1B—C1N—C2B—C11B	−25.17 (19)
N4B—N3B—C2B—C1N	−174.73 (11)	C17B—C1N—C2B—N3B	−27.49 (17)
N3B—N4B—C5B—C6B	−4.06 (19)	C17B—C1N—C2B—C11B	154.46 (12)
N3B—N4B—C5B—C10B	174.91 (12)	O1B—C1N—C17B—C18B	−39.39 (18)
O1A—C1A—C17A—C18A	130.34 (15)	O1B—C1N—C17B—C22B	133.37 (14)
C17A—C1A—C2A—C11A	164.58 (12)	C2B—C1N—C17B—C18B	140.98 (13)
O1A—C1A—C2A—N3A	161.29 (13)	C2B—C1N—C17B—C22B	−46.26 (18)
O1A—C1A—C2A—C11A	−15.14 (19)	N3B—C2B—C11B—C12B	129.24 (15)
C17A—C1A—C2A—N3A	−18.99 (17)	N3B—C2B—C11B—C16B	−50.4 (2)
C2A—C1A—C17A—C22A	136.87 (14)	C1N—C2B—C11B—C12B	−52.99 (18)
O1A—C1A—C17A—C22A	−43.40 (19)	C1N—C2B—C11B—C16B	127.42 (14)
C2A—C1A—C17A—C18A	−49.38 (18)	N4B—C5B—C6B—C7B	177.99 (13)
C1A—C2A—C11A—C12A	−116.71 (16)	C10B—C5B—C6B—C7B	−1.0 (2)
C1A—C2A—C11A—C16A	65.64 (18)	N4B—C5B—C10B—C9B	−178.04 (13)
N3A—C2A—C11A—C16A	−110.42 (17)	C6B—C5B—C10B—C9B	1.0 (2)
N3A—C2A—C11A—C12A	67.2 (2)	C5B—C6B—C7B—C8B	0.0 (2)
C10A—C5A—C6A—C7A	0.4 (2)	C6B—C7B—C8B—C9B	1.0 (2)
N4A—C5A—C6A—C7A	−178.91 (13)	C7B—C8B—C9B—C10B	−1.0 (2)
C6A—C5A—C10A—C9A	−0.7 (2)	C8B—C9B—C10B—C5B	0.0 (2)
N4A—C5A—C10A—C9A	178.67 (13)	C2B—C11B—C12B—C13B	−178.81 (14)
C5A—C6A—C7A—C8A	0.2 (2)	C16B—C11B—C12B—C13B	0.8 (2)
C6A—C7A—C8A—C9A	−0.5 (2)	C2B—C11B—C16B—C15B	178.32 (13)
C7A—C8A—C9A—C10A	0.2 (2)	C12B—C11B—C16B—C15B	−1.3 (2)
C8A—C9A—C10A—C5A	0.4 (2)	C11B—C12B—C13B—C14B	0.3 (3)
C2A—C11A—C12A—C13A	−178.51 (18)	C12B—C13B—C14B—C15B	−0.9 (3)
C16A—C11A—C12A—C13A	−0.8 (3)	C13B—C14B—C15B—C16B	0.4 (2)
C2A—C11A—C16A—C15A	178.20 (16)	C14B—C15B—C16B—C11B	0.7 (2)
C12A—C11A—C16A—C15A	0.5 (3)	C1N—C17B—C18B—C19B	173.38 (13)
C11A—C12A—C13A—C14A	0.2 (3)	C22B—C17B—C18B—C19B	0.4 (2)
C12A—C13A—C14A—C15A	0.7 (4)	C1N—C17B—C22B—C21B	−171.30 (14)
C13A—C14A—C15A—C16A	−0.9 (4)	C18B—C17B—C22B—C21B	1.5 (2)
C14A—C15A—C16A—C11A	0.3 (3)	C17B—C18B—C19B—C20B	−1.7 (2)
C1A—C17A—C18A—C19A	−171.81 (14)	C18B—C19B—C20B—C21B	1.1 (2)
C1A—C17A—C22A—C21A	173.61 (15)	C19B—C20B—C21B—C22B	0.8 (3)
C18A—C17A—C22A—C21A	−0.3 (2)	C20B—C21B—C22B—C17B	−2.1 (2)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) x−1, y−1, z; (v) x+1, y+1, z; (vi) x, y, z+1; (vii) x, y−1, z+1; (viii) −x, −y+1, −z+1; (ix) −x, −y+2, −z+1; (x) x, y+1, z; (xi) −x+1, −y+1, −z; (xii) x, y−1, z; (xiii) x, y, z−1; (xiv) x, y+1, z−1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H4A···O1B^ii	0.86 (2)	2.52 (1)	3.0793 (17)	124 (1)
C10B—H10B···O1A^i	0.93	2.51	3.2690 (18)	139
C10A—H10A···Cg1^ii	0.93	2.70	3.5487 (17)	152
C8A—H8A···Cg2^viii	0.93	2.86	3.6754 (19)	146

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (viii) −x, −y+1, −z+1.