(E)-1-(2,4-Di-nitro-benzyl-idene)-2,2-di-phenyl-hydrazine.

In the crystal of the title compound, C19H14N4O4, the asymmetric unit consists of two discrete mol-ecules. The C=N bonds in both mol-ecules show an E conformation. The dihedral angles between the C atoms of the 2,4-dinitrobenzene rings and the C=N-N planes are 13.52 (9) and 13.82 (9)° for the two mol-ecules. In the crystal, C-H⋯O hydrogen bonds, mainly between the phenyl ring and the nitro group along the b axis.

Related literature

For the synthesis and related structures, see: Vicini et al. (2002 ▶); Rollas et al. (2002 ▶); Mendoza et al. (2012 ▶). For applications of hydrazones, see: Angell et al. (2006 ▶); Clulow et al. (2008 ▶); Motherwell & Ramsay (2007 ▶).

Experimental

Crystal data

C19H14N4O4

M = 362.34

Triclinic,

a = 7.0288 (6) Å

b = 13.5001 (7) Å

c = 17.9271 (11) Å

α = 91.878 (5)°

β = 93.431 (6)°

γ = 91.548 (6)°

V = 1696.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.59 × 0.38 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.955, T max = 0.988

13303 measured reflections

6694 independent reflections

3465 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.079

S = 1.01

6694 reflections

487 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014360/bt6909sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014360/bt6909Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014360/bt6909Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H14N4O4	Z = 4
Mr = 362.34	F(000) = 752
Triclinic, P1	Dx = 1.419 Mg m−3
a = 7.0288 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.5001 (7) Å	Cell parameters from 4321 reflections
c = 17.9271 (11) Å	θ = 3.4–26.0°
α = 91.878 (5)°	µ = 0.10 mm−1
β = 93.431 (6)°	T = 298 K
γ = 91.548 (6)°	Prism, red
V = 1696.4 (2) Å3	0.59 × 0.38 × 0.12 mm

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	6694 independent reflections
Graphite monochromator	3465 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.028
ω scans	θmax = 26.1°, θmin = 3.4°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −8→7
Tmin = 0.955, Tmax = 0.988	k = −13→16
13303 measured reflections	l = −21→22

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0255P)2] where P = (Fo2 + 2Fc2)/3
6694 reflections	(Δ/σ)max = 0.001
487 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.2 e Å−3

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

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 > 2σ(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.

	x	y	z	Uiso*/Ueq
C1A	0.3668 (2)	−0.02195 (12)	0.81399 (8)	0.0351 (4)
C2A	0.3795 (2)	−0.12554 (12)	0.81250 (8)	0.0351 (4)
C3A	0.3529 (2)	−0.18098 (12)	0.87481 (8)	0.0410 (4)
H3A	0.3639	−0.2495	0.8725	0.049*
C4A	0.3103 (2)	−0.13346 (13)	0.93960 (8)	0.0412 (4)
C5A	0.2958 (2)	−0.03170 (13)	0.94464 (9)	0.0475 (5)
H5A	0.2669	−0.0001	0.9893	0.057*
C6A	0.3250 (2)	0.02177 (13)	0.88257 (8)	0.0448 (4)
H6A	0.3166	0.0904	0.8862	0.054*
C7A	0.3967 (2)	0.04206 (13)	0.75145 (9)	0.0416 (4)
H7A	0.4005	0.0166	0.7027	0.05*
C8A	0.4850 (2)	0.29930 (12)	0.73592 (9)	0.0380 (4)
C9A	0.5557 (2)	0.32258 (13)	0.80812 (9)	0.0443 (4)
H9A	0.5802	0.2725	0.8414	0.053*
C10A	0.5895 (2)	0.42039 (15)	0.83049 (10)	0.0528 (5)
H10A	0.6363	0.4358	0.8792	0.063*
C11A	0.5552 (3)	0.49555 (14)	0.78203 (12)	0.0597 (5)
H11A	0.5781	0.5614	0.7977	0.072*
C12A	0.4870 (3)	0.47210 (14)	0.71041 (11)	0.0573 (5)
H12A	0.4641	0.5225	0.6772	0.069*
C13A	0.4517 (2)	0.37495 (13)	0.68692 (10)	0.0493 (5)
H13A	0.4054	0.3601	0.638	0.059*
C14A	0.4312 (3)	0.17046 (12)	0.63452 (9)	0.0436 (4)
C15A	0.5912 (3)	0.17379 (13)	0.59397 (10)	0.0556 (5)
H15A	0.7088	0.1936	0.6169	0.067*
C16A	0.5746 (3)	0.14724 (15)	0.51853 (11)	0.0667 (6)
H16A	0.6818	0.15	0.4905	0.08*
C17A	0.4022 (4)	0.11692 (15)	0.48480 (11)	0.0685 (6)
H17A	0.3926	0.0983	0.4343	0.082*
C18A	0.2445 (3)	0.11405 (15)	0.52541 (10)	0.0679 (6)
H18A	0.1273	0.0933	0.5025	0.082*
C19A	0.2574 (3)	0.14172 (14)	0.60044 (10)	0.0563 (5)
H19A	0.1489	0.1409	0.6277	0.068*
N1A	0.41773 (19)	0.13568 (10)	0.76728 (7)	0.0412 (4)
N2A	0.4450 (2)	0.19996 (10)	0.71228 (7)	0.0460 (4)
N3A	0.4219 (2)	−0.18328 (11)	0.74490 (8)	0.0446 (4)
N4A	0.2742 (2)	−0.19203 (14)	1.00492 (9)	0.0588 (4)
O1A	0.4180 (2)	−0.14424 (10)	0.68499 (7)	0.0713 (4)
O2A	0.4573 (2)	−0.27067 (10)	0.75110 (7)	0.0690 (4)
O3A	0.2800 (2)	−0.28198 (11)	0.99918 (7)	0.0854 (5)
O4A	0.2412 (2)	−0.14791 (11)	1.06275 (7)	0.0868 (5)
C1B	1.0722 (2)	0.48446 (12)	0.81436 (8)	0.0360 (4)
C2B	1.0599 (2)	0.38024 (12)	0.81056 (8)	0.0362 (4)
C3B	1.1091 (2)	0.32368 (13)	0.87149 (9)	0.0437 (4)
H3B	1.0986	0.2549	0.8675	0.052*
C4B	1.1730 (2)	0.36977 (13)	0.93732 (9)	0.0431 (4)
C5B	1.1862 (2)	0.47202 (13)	0.94478 (9)	0.0472 (5)
H5B	1.2284	0.5031	0.9901	0.057*
C6B	1.1357 (2)	0.52650 (13)	0.88409 (9)	0.0462 (5)
H6B	1.1441	0.5953	0.8895	0.055*
C7B	1.0249 (2)	0.54984 (13)	0.75336 (9)	0.0418 (4)
H7B	1.006	0.5257	0.7042	0.05*
C8B	0.9320 (2)	0.80531 (12)	0.73992 (9)	0.0388 (4)
C9B	0.8888 (2)	0.82648 (13)	0.81281 (9)	0.0457 (5)
H9B	0.8825	0.776	0.8467	0.055*
C10B	0.8550 (2)	0.92275 (14)	0.83500 (10)	0.0538 (5)
H10B	0.8278	0.937	0.8843	0.065*
C11B	0.8608 (2)	0.99803 (14)	0.78533 (11)	0.0578 (5)
H11B	0.838	1.0628	0.8009	0.069*
C12B	0.9002 (3)	0.97709 (14)	0.71319 (11)	0.0549 (5)
H12B	0.903	1.0278	0.6794	0.066*
C13B	0.9361 (2)	0.88092 (13)	0.68955 (10)	0.0482 (5)
H13B	0.9628	0.8672	0.6401	0.058*
C14B	0.9507 (3)	0.67717 (12)	0.63857 (9)	0.0427 (4)
C15B	1.1080 (3)	0.66776 (14)	0.59758 (10)	0.0567 (5)
H15B	1.2294	0.6803	0.62	0.068*
C16B	1.0852 (3)	0.63946 (15)	0.52263 (11)	0.0677 (6)
H16B	1.1914	0.6339	0.4944	0.081*
C17B	0.9074 (4)	0.61979 (15)	0.49027 (11)	0.0685 (6)
H17B	0.8927	0.6	0.44	0.082*
C18B	0.7515 (3)	0.62890 (16)	0.53095 (11)	0.0694 (6)
H18B	0.6305	0.6152	0.5085	0.083*
C19B	0.7723 (3)	0.65841 (14)	0.60565 (10)	0.0562 (5)
H19B	0.6654	0.6655	0.6334	0.067*
N1B	1.01036 (19)	0.64297 (11)	0.77055 (7)	0.0423 (4)
N2B	0.9722 (2)	0.70762 (10)	0.71597 (7)	0.0464 (4)
N3B	0.99175 (19)	0.32343 (12)	0.74256 (8)	0.0462 (4)
N4B	1.2312 (2)	0.31012 (14)	1.00096 (9)	0.0610 (5)
O1B	0.9506 (2)	0.36593 (10)	0.68571 (7)	0.0697 (4)
O2B	0.9778 (2)	0.23333 (10)	0.74548 (7)	0.0749 (4)
O3B	1.2219 (2)	0.22001 (11)	0.99330 (8)	0.0905 (5)
O4B	1.2854 (2)	0.35333 (11)	1.05901 (7)	0.0901 (5)

	U11	U22	U33	U12	U13	U23
C1A	0.0376 (10)	0.0321 (10)	0.0351 (9)	−0.0016 (8)	−0.0020 (7)	0.0028 (8)
C2A	0.0374 (10)	0.0326 (10)	0.0348 (9)	−0.0022 (8)	0.0020 (7)	−0.0018 (8)
C3A	0.0477 (11)	0.0318 (10)	0.0430 (10)	−0.0044 (8)	−0.0008 (8)	0.0051 (9)
C4A	0.0549 (12)	0.0377 (11)	0.0304 (9)	−0.0075 (9)	−0.0021 (8)	0.0077 (8)
C5A	0.0645 (13)	0.0428 (12)	0.0344 (10)	−0.0035 (9)	0.0010 (8)	−0.0039 (9)
C6A	0.0660 (13)	0.0305 (10)	0.0377 (10)	0.0005 (9)	0.0036 (8)	0.0008 (8)
C7A	0.0545 (12)	0.0338 (11)	0.0365 (10)	−0.0010 (8)	0.0022 (8)	0.0034 (8)
C8A	0.0429 (11)	0.0321 (10)	0.0395 (10)	0.0000 (8)	0.0043 (8)	0.0072 (9)
C9A	0.0516 (12)	0.0378 (12)	0.0439 (11)	0.0003 (9)	0.0039 (8)	0.0046 (9)
C10A	0.0499 (13)	0.0520 (13)	0.0559 (12)	−0.0037 (10)	0.0062 (9)	−0.0088 (11)
C11A	0.0595 (14)	0.0357 (12)	0.0846 (15)	−0.0021 (10)	0.0140 (11)	−0.0042 (12)
C12A	0.0649 (14)	0.0379 (13)	0.0707 (14)	0.0035 (10)	0.0090 (10)	0.0150 (11)
C13A	0.0572 (13)	0.0409 (12)	0.0499 (11)	−0.0004 (9)	0.0013 (9)	0.0089 (10)
C14A	0.0618 (13)	0.0313 (10)	0.0375 (10)	−0.0030 (9)	0.0005 (9)	0.0074 (8)
C15A	0.0662 (14)	0.0489 (13)	0.0523 (12)	−0.0005 (10)	0.0063 (10)	0.0056 (10)
C16A	0.0890 (18)	0.0579 (14)	0.0563 (14)	0.0077 (12)	0.0275 (12)	0.0038 (11)
C17A	0.111 (2)	0.0536 (14)	0.0410 (12)	−0.0023 (13)	0.0057 (13)	−0.0003 (10)
C18A	0.0920 (18)	0.0619 (15)	0.0474 (13)	−0.0137 (12)	−0.0101 (11)	0.0053 (11)
C19A	0.0671 (14)	0.0579 (14)	0.0437 (11)	−0.0080 (10)	0.0036 (9)	0.0064 (10)
N1A	0.0517 (9)	0.0342 (9)	0.0375 (8)	−0.0021 (7)	−0.0003 (6)	0.0072 (7)
N2A	0.0691 (11)	0.0348 (9)	0.0336 (8)	−0.0071 (7)	0.0006 (7)	0.0058 (7)
N3A	0.0510 (10)	0.0381 (10)	0.0448 (9)	−0.0026 (7)	0.0079 (7)	−0.0020 (8)
N4A	0.0820 (13)	0.0540 (12)	0.0399 (10)	−0.0132 (9)	0.0016 (8)	0.0081 (9)
O1A	0.1278 (13)	0.0501 (9)	0.0383 (7)	0.0053 (8)	0.0231 (7)	0.0027 (7)
O2A	0.1049 (12)	0.0346 (9)	0.0691 (9)	0.0124 (7)	0.0155 (7)	−0.0033 (7)
O3A	0.1557 (16)	0.0426 (9)	0.0587 (9)	−0.0129 (9)	0.0137 (9)	0.0140 (8)
O4A	0.1535 (15)	0.0685 (11)	0.0396 (8)	−0.0074 (10)	0.0179 (8)	0.0064 (8)
C1B	0.0402 (11)	0.0340 (11)	0.0345 (9)	0.0021 (8)	0.0068 (7)	0.0026 (8)
C2B	0.0395 (10)	0.0354 (10)	0.0339 (9)	0.0030 (8)	0.0038 (7)	−0.0022 (8)
C3B	0.0516 (12)	0.0352 (11)	0.0452 (11)	0.0066 (9)	0.0070 (8)	0.0042 (9)
C4B	0.0538 (12)	0.0420 (12)	0.0351 (10)	0.0103 (9)	0.0069 (8)	0.0083 (9)
C5B	0.0643 (13)	0.0458 (12)	0.0317 (10)	0.0033 (9)	0.0039 (8)	−0.0017 (9)
C6B	0.0635 (13)	0.0340 (11)	0.0409 (10)	0.0002 (9)	0.0032 (8)	0.0002 (9)
C7B	0.0538 (12)	0.0366 (11)	0.0349 (9)	0.0008 (8)	0.0020 (8)	0.0031 (9)
C8B	0.0406 (11)	0.0339 (11)	0.0414 (10)	0.0024 (8)	−0.0027 (7)	0.0046 (9)
C9B	0.0490 (12)	0.0419 (12)	0.0460 (11)	0.0007 (9)	0.0008 (8)	0.0024 (9)
C10B	0.0548 (13)	0.0503 (13)	0.0556 (12)	0.0033 (10)	0.0030 (9)	−0.0098 (10)
C11B	0.0521 (13)	0.0383 (12)	0.0818 (15)	0.0026 (9)	−0.0021 (10)	−0.0079 (11)
C12B	0.0593 (13)	0.0368 (12)	0.0689 (14)	0.0008 (9)	−0.0005 (10)	0.0126 (11)
C13B	0.0557 (12)	0.0423 (12)	0.0466 (11)	0.0039 (9)	0.0006 (8)	0.0067 (10)
C14B	0.0629 (13)	0.0317 (10)	0.0343 (10)	0.0052 (9)	0.0050 (9)	0.0068 (8)
C15B	0.0675 (14)	0.0511 (13)	0.0512 (12)	0.0017 (10)	0.0044 (10)	−0.0021 (10)
C16B	0.0894 (18)	0.0611 (15)	0.0548 (14)	0.0069 (12)	0.0220 (12)	−0.0021 (11)
C17B	0.109 (2)	0.0566 (14)	0.0399 (12)	0.0101 (13)	0.0019 (13)	−0.0022 (10)
C18B	0.0815 (17)	0.0714 (16)	0.0530 (13)	0.0022 (12)	−0.0137 (11)	−0.0016 (12)
C19B	0.0649 (14)	0.0565 (13)	0.0473 (12)	0.0032 (10)	0.0021 (10)	0.0032 (10)
N1B	0.0517 (9)	0.0372 (9)	0.0382 (8)	0.0025 (7)	0.0024 (6)	0.0059 (7)
N2B	0.0725 (11)	0.0360 (9)	0.0311 (8)	0.0110 (8)	0.0003 (7)	0.0069 (7)
N3B	0.0502 (10)	0.0421 (11)	0.0461 (9)	0.0024 (8)	0.0040 (7)	−0.0042 (8)
N4B	0.0870 (13)	0.0562 (12)	0.0406 (10)	0.0167 (10)	0.0008 (8)	0.0087 (9)
O1B	0.1135 (12)	0.0541 (9)	0.0390 (7)	−0.0086 (8)	−0.0118 (7)	0.0014 (7)
O2B	0.1153 (13)	0.0330 (9)	0.0734 (10)	0.0007 (8)	−0.0151 (8)	−0.0063 (7)
O3B	0.1567 (16)	0.0456 (10)	0.0692 (10)	0.0218 (10)	−0.0085 (9)	0.0147 (9)
O4B	0.1533 (16)	0.0728 (11)	0.0427 (9)	0.0195 (10)	−0.0149 (9)	0.0048 (8)

C1A—C6A	1.397 (2)	C1B—C6B	1.399 (2)
C1A—C2A	1.403 (2)	C1B—C2B	1.406 (2)
C1A—C7A	1.459 (2)	C1B—C7B	1.456 (2)
C2A—C3A	1.3839 (19)	C2B—C3B	1.386 (2)
C2A—N3A	1.469 (2)	C2B—N3B	1.467 (2)
C3A—C4A	1.361 (2)	C3B—C4B	1.362 (2)
C3A—H3A	0.93	C3B—H3B	0.93
C4A—C5A	1.381 (2)	C4B—C5B	1.383 (2)
C4A—N4A	1.4650 (19)	C4B—N4B	1.463 (2)
C5A—C6A	1.369 (2)	C5B—C6B	1.368 (2)
C5A—H5A	0.93	C5B—H5B	0.93
C6A—H6A	0.93	C6B—H6B	0.93
C7A—N1A	1.2888 (19)	C7B—N1B	1.293 (2)
C7A—H7A	0.93	C7B—H7B	0.93
C8A—C9A	1.381 (2)	C8B—C9B	1.382 (2)
C8A—C13A	1.384 (2)	C8B—C13B	1.386 (2)
C8A—N2A	1.409 (2)	C8B—N2B	1.414 (2)
C9A—C10A	1.378 (2)	C9B—C10B	1.378 (2)
C9A—H9A	0.93	C9B—H9B	0.93
C10A—C11A	1.374 (2)	C10B—C11B	1.374 (2)
C10A—H10A	0.93	C10B—H10B	0.93
C11A—C12A	1.368 (2)	C11B—C12B	1.361 (2)
C11A—H11A	0.93	C11B—H11B	0.93
C12A—C13A	1.376 (2)	C12B—C13B	1.387 (2)
C12A—H12A	0.93	C12B—H12B	0.93
C13A—H13A	0.93	C13B—H13B	0.93
C14A—C19A	1.373 (2)	C14B—C19B	1.367 (2)
C14A—C15A	1.376 (2)	C14B—C15B	1.370 (2)
C14A—N2A	1.434 (2)	C14B—N2B	1.432 (2)
C15A—C16A	1.385 (2)	C15B—C16B	1.384 (2)
C15A—H15A	0.93	C15B—H15B	0.93
C16A—C17A	1.368 (3)	C16B—C17B	1.362 (3)
C16A—H16A	0.93	C16B—H16B	0.93
C17A—C18A	1.362 (3)	C17B—C18B	1.359 (3)
C17A—H17A	0.93	C17B—H17B	0.93
C18A—C19A	1.381 (2)	C18B—C19B	1.383 (2)
C18A—H18A	0.93	C18B—H18B	0.93
C19A—H19A	0.93	C19B—H19B	0.93
N1A—N2A	1.3534 (16)	N1B—N2B	1.3521 (16)
N3A—O1A	1.2110 (15)	N3B—O1B	1.2097 (16)
N3A—O2A	1.2195 (16)	N3B—O2B	1.2207 (17)
N4A—O4A	1.2162 (19)	N4B—O4B	1.2121 (19)
N4A—O3A	1.2173 (19)	N4B—O3B	1.2193 (19)
C6A—C1A—C2A	115.60 (14)	C6B—C1B—C2B	115.16 (15)
C6A—C1A—C7A	118.58 (15)	C6B—C1B—C7B	118.81 (16)
C2A—C1A—C7A	125.81 (15)	C2B—C1B—C7B	126.02 (15)
C3A—C2A—C1A	122.35 (15)	C3B—C2B—C1B	122.16 (15)
C3A—C2A—N3A	114.98 (14)	C3B—C2B—N3B	115.05 (15)
C1A—C2A—N3A	122.67 (14)	C1B—C2B—N3B	122.78 (14)
C4A—C3A—C2A	118.84 (15)	C4B—C3B—C2B	119.39 (17)
C4A—C3A—H3A	120.6	C4B—C3B—H3B	120.3
C2A—C3A—H3A	120.6	C2B—C3B—H3B	120.3
C3A—C4A—C5A	121.56 (15)	C3B—C4B—C5B	121.14 (16)
C3A—C4A—N4A	119.13 (16)	C3B—C4B—N4B	119.48 (17)
C5A—C4A—N4A	119.29 (16)	C5B—C4B—N4B	119.38 (17)
C6A—C5A—C4A	118.61 (16)	C6B—C5B—C4B	118.54 (17)
C6A—C5A—H5A	120.7	C6B—C5B—H5B	120.7
C4A—C5A—H5A	120.7	C4B—C5B—H5B	120.7
C5A—C6A—C1A	123.03 (16)	C5B—C6B—C1B	123.59 (17)
C5A—C6A—H6A	118.5	C5B—C6B—H6B	118.2
C1A—C6A—H6A	118.5	C1B—C6B—H6B	118.2
N1A—C7A—C1A	116.49 (15)	N1B—C7B—C1B	117.04 (15)
N1A—C7A—H7A	121.8	N1B—C7B—H7B	121.5
C1A—C7A—H7A	121.8	C1B—C7B—H7B	121.5
C9A—C8A—C13A	119.23 (17)	C9B—C8B—C13B	119.49 (17)
C9A—C8A—N2A	120.69 (15)	C9B—C8B—N2B	120.98 (15)
C13A—C8A—N2A	120.08 (15)	C13B—C8B—N2B	119.52 (15)
C10A—C9A—C8A	119.67 (16)	C10B—C9B—C8B	119.67 (17)
C10A—C9A—H9A	120.2	C10B—C9B—H9B	120.2
C8A—C9A—H9A	120.2	C8B—C9B—H9B	120.2
C11A—C10A—C9A	121.12 (18)	C11B—C10B—C9B	120.93 (18)
C11A—C10A—H10A	119.4	C11B—C10B—H10B	119.5
C9A—C10A—H10A	119.4	C9B—C10B—H10B	119.5
C12A—C11A—C10A	119.00 (19)	C12B—C11B—C10B	119.50 (19)
C12A—C11A—H11A	120.5	C12B—C11B—H11B	120.3
C10A—C11A—H11A	120.5	C10B—C11B—H11B	120.3
C11A—C12A—C13A	120.86 (18)	C11B—C12B—C13B	120.72 (18)
C11A—C12A—H12A	119.6	C11B—C12B—H12B	119.6
C13A—C12A—H12A	119.6	C13B—C12B—H12B	119.6
C12A—C13A—C8A	120.11 (18)	C8B—C13B—C12B	119.66 (17)
C12A—C13A—H13A	119.9	C8B—C13B—H13B	120.2
C8A—C13A—H13A	119.9	C12B—C13B—H13B	120.2
C19A—C14A—C15A	120.34 (17)	C19B—C14B—C15B	120.19 (18)
C19A—C14A—N2A	119.85 (16)	C19B—C14B—N2B	119.65 (17)
C15A—C14A—N2A	119.78 (16)	C15B—C14B—N2B	120.16 (17)
C14A—C15A—C16A	119.11 (18)	C14B—C15B—C16B	119.62 (19)
C14A—C15A—H15A	120.4	C14B—C15B—H15B	120.2
C16A—C15A—H15A	120.4	C16B—C15B—H15B	120.2
C17A—C16A—C15A	120.6 (2)	C17B—C16B—C15B	120.0 (2)
C17A—C16A—H16A	119.7	C17B—C16B—H16B	120
C15A—C16A—H16A	119.7	C15B—C16B—H16B	120
C18A—C17A—C16A	119.8 (2)	C18B—C17B—C16B	120.4 (2)
C18A—C17A—H17A	120.1	C18B—C17B—H17B	119.8
C16A—C17A—H17A	120.1	C16B—C17B—H17B	119.8
C17A—C18A—C19A	120.44 (19)	C17B—C18B—C19B	120.2 (2)
C17A—C18A—H18A	119.8	C17B—C18B—H18B	119.9
C19A—C18A—H18A	119.8	C19B—C18B—H18B	119.9
C14A—C19A—C18A	119.64 (18)	C14B—C19B—C18B	119.65 (19)
C14A—C19A—H19A	120.2	C14B—C19B—H19B	120.2
C18A—C19A—H19A	120.2	C18B—C19B—H19B	120.2
C7A—N1A—N2A	120.05 (14)	C7B—N1B—N2B	119.66 (14)
N1A—N2A—C8A	115.78 (13)	N1B—N2B—C8B	116.16 (13)
N1A—N2A—C14A	122.80 (14)	N1B—N2B—C14B	122.32 (14)
C8A—N2A—C14A	121.41 (13)	C8B—N2B—C14B	121.11 (13)
O1A—N3A—O2A	121.87 (15)	O1B—N3B—O2B	121.78 (16)
O1A—N3A—C2A	119.95 (14)	O1B—N3B—C2B	120.07 (15)
O2A—N3A—C2A	118.17 (14)	O2B—N3B—C2B	118.16 (15)
O4A—N4A—O3A	123.09 (16)	O4B—N4B—O3B	123.35 (17)
O4A—N4A—C4A	118.02 (17)	O4B—N4B—C4B	117.89 (18)
O3A—N4A—C4A	118.88 (17)	O3B—N4B—C4B	118.76 (18)
C6A—C1A—C2A—C3A	−0.1 (2)	C6B—C1B—C2B—C3B	−0.6 (2)
C7A—C1A—C2A—C3A	178.63 (15)	C7B—C1B—C2B—C3B	179.58 (15)
C6A—C1A—C2A—N3A	179.84 (14)	C6B—C1B—C2B—N3B	178.50 (14)
C7A—C1A—C2A—N3A	−1.4 (2)	C7B—C1B—C2B—N3B	−1.3 (2)
C1A—C2A—C3A—C4A	0.9 (2)	C1B—C2B—C3B—C4B	−0.5 (2)
N3A—C2A—C3A—C4A	−179.06 (14)	N3B—C2B—C3B—C4B	−179.67 (15)
C2A—C3A—C4A—C5A	−0.9 (2)	C2B—C3B—C4B—C5B	1.3 (3)
C2A—C3A—C4A—N4A	177.51 (14)	C2B—C3B—C4B—N4B	−177.95 (14)
C3A—C4A—C5A—C6A	0.1 (3)	C3B—C4B—C5B—C6B	−0.8 (3)
N4A—C4A—C5A—C6A	−178.28 (15)	N4B—C4B—C5B—C6B	178.37 (14)
C4A—C5A—C6A—C1A	0.7 (3)	C4B—C5B—C6B—C1B	−0.4 (3)
C2A—C1A—C6A—C5A	−0.7 (2)	C2B—C1B—C6B—C5B	1.1 (2)
C7A—C1A—C6A—C5A	−179.55 (15)	C7B—C1B—C6B—C5B	−179.12 (15)
C6A—C1A—C7A—N1A	12.6 (2)	C6B—C1B—C7B—N1B	−12.5 (2)
C2A—C1A—C7A—N1A	−166.14 (15)	C2B—C1B—C7B—N1B	167.26 (16)
C13A—C8A—C9A—C10A	0.8 (2)	C13B—C8B—C9B—C10B	−1.6 (2)
N2A—C8A—C9A—C10A	−178.48 (16)	N2B—C8B—C9B—C10B	178.39 (15)
C8A—C9A—C10A—C11A	−0.4 (3)	C8B—C9B—C10B—C11B	1.0 (3)
C9A—C10A—C11A—C12A	−0.2 (3)	C9B—C10B—C11B—C12B	0.1 (3)
C10A—C11A—C12A—C13A	0.4 (3)	C10B—C11B—C12B—C13B	−0.6 (3)
C11A—C12A—C13A—C8A	0.0 (3)	C9B—C8B—C13B—C12B	1.2 (2)
C9A—C8A—C13A—C12A	−0.6 (2)	N2B—C8B—C13B—C12B	−178.84 (15)
N2A—C8A—C13A—C12A	178.65 (16)	C11B—C12B—C13B—C8B	0.0 (3)
C19A—C14A—C15A—C16A	−0.4 (3)	C19B—C14B—C15B—C16B	0.2 (3)
N2A—C14A—C15A—C16A	−178.53 (16)	N2B—C14B—C15B—C16B	−179.22 (16)
C14A—C15A—C16A—C17A	−0.8 (3)	C14B—C15B—C16B—C17B	−0.9 (3)
C15A—C16A—C17A—C18A	0.9 (3)	C15B—C16B—C17B—C18B	0.8 (3)
C16A—C17A—C18A—C19A	0.1 (3)	C16B—C17B—C18B—C19B	0.1 (3)
C15A—C14A—C19A—C18A	1.4 (3)	C15B—C14B—C19B—C18B	0.7 (3)
N2A—C14A—C19A—C18A	179.54 (17)	N2B—C14B—C19B—C18B	−179.92 (17)
C17A—C18A—C19A—C14A	−1.3 (3)	C17B—C18B—C19B—C14B	−0.8 (3)
C1A—C7A—N1A—N2A	−179.63 (13)	C1B—C7B—N1B—N2B	178.10 (13)
C7A—N1A—N2A—C8A	−174.03 (15)	C7B—N1B—N2B—C8B	171.41 (15)
C7A—N1A—N2A—C14A	7.1 (2)	C7B—N1B—N2B—C14B	−1.3 (2)
C9A—C8A—N2A—N1A	21.3 (2)	C9B—C8B—N2B—N1B	−15.2 (2)
C13A—C8A—N2A—N1A	−157.96 (14)	C13B—C8B—N2B—N1B	164.80 (14)
C9A—C8A—N2A—C14A	−159.80 (16)	C9B—C8B—N2B—C14B	157.63 (15)
C13A—C8A—N2A—C14A	20.9 (2)	C13B—C8B—N2B—C14B	−22.4 (2)
C19A—C14A—N2A—N1A	68.4 (2)	C19B—C14B—N2B—N1B	96.7 (2)
C15A—C14A—N2A—N1A	−113.47 (18)	C15B—C14B—N2B—N1B	−83.9 (2)
C19A—C14A—N2A—C8A	−110.43 (18)	C19B—C14B—N2B—C8B	−75.7 (2)
C15A—C14A—N2A—C8A	67.7 (2)	C15B—C14B—N2B—C8B	103.7 (2)
C3A—C2A—N3A—O1A	168.42 (15)	C3B—C2B—N3B—O1B	−177.83 (14)
C1A—C2A—N3A—O1A	−11.5 (2)	C1B—C2B—N3B—O1B	3.0 (2)
C3A—C2A—N3A—O2A	−10.4 (2)	C3B—C2B—N3B—O2B	2.4 (2)
C1A—C2A—N3A—O2A	169.66 (15)	C1B—C2B—N3B—O2B	−176.76 (15)
C3A—C4A—N4A—O4A	178.13 (17)	C3B—C4B—N4B—O4B	−179.18 (17)
C5A—C4A—N4A—O4A	−3.4 (2)	C5B—C4B—N4B—O4B	1.6 (2)
C3A—C4A—N4A—O3A	−1.2 (2)	C3B—C4B—N4B—O3B	0.4 (3)
C5A—C4A—N4A—O3A	177.22 (17)	C5B—C4B—N4B—O3B	−178.81 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C11A—H11A···O2Ai	0.93	2.59	3.306 (2)	134
C11B—H11B···O2Bi	0.93	2.72	3.370 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11A—H11A⋯O2A i	0.93	2.59	3.306 (2)	134
C11B—H11B⋯O2B i	0.93	2.72	3.370 (2)	128

Symmetry code: (i) .