(2Z)-2-Anilino-2-[oxido(phen-yl)iminio]-N-(2-pyrid-yl)acetamide methanol 0.425-solvate.

The title compound, C(19)H(16)N(4)O(2)·0.425CH(4)O, crystallizes with two formula units per asymmetric unit. Researching its crystal structure constitutes part of a study of the nature of inter-actions between the N(+)-O(-) group and the vicinal NH group. The nitrone group and methanol solvent mol-ecules are linked via four N-H⋯O and one O-H⋯O hydrogen bonds, with donor-acceptor distances of 2.603 (3)-2.730 (3) and 2.770 (3) Å, respectively. The crystal structure also involves two intermolecular N-H⋯N hydrogen bonds.

Related literature

For literature related to the synthesis of the title compound, see: Branco et al. (1992 ▶); Aurich (1968 ▶); Guimanini et al. (1999 ▶); Szantay et al. (1965 ▶); Southan et al. (1998 ▶); Warshaw et al. (1989 ▶). For literature on nitro­nes as an active equivalent of the C=O group, see: Boruah et al. (2003 ▶); Freisleben et al. (2002 ▶); Saito et al. (2001 ▶); Gravestock et al. (2000 ▶); Torssell (1988 ▶). For examples of nitro­nes with a vicinal NH group, see: Janzen et al. (1997 ▶); Clement et al. (1987 ▶); Baranowska et al. (1977 ▶); Aurich et al. (1976 ▶); Rosenberg et al. (1972 ▶). For literature on the medical use of these compounds, see: Floyd (2006 ▶). For related literature, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H16N4O2·0.425CH4O

M = 345.98

Monoclinic,

a = 18.7604 (3) Å

b = 9.4701 (2) Å

c = 21.2839 (5) Å

β = 104.375 (1)°

V = 3662.97 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.11 × 0.09 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.991, T max = 0.998

12501 measured reflections

6668 independent reflections

3520 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.156

S = 1.03

6668 reflections

474 parameters

548 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.14 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003346/er2043sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003346/er2043Isup2.hkl

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

C19H16N4O2·0.425CH4O	F(000) = 1453
Mr = 345.98	Dx = 1.255 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.7604 (3) Å	Cell parameters from 6743 reflections
b = 9.4701 (2) Å	θ = 1.0–25.4°
c = 21.2839 (5) Å	µ = 0.09 mm−1
β = 104.375 (1)°	T = 293 K
V = 3662.97 (13) Å3	Plate, colourless
Z = 8	0.11 × 0.09 × 0.02 mm

Nonius KappaCCD diffractometer	6668 independent reflections
Radiation source: fine-focus sealed tube	3520 reflections with I > 2σ(I)
horizontally mounted graphite crystal	Rint = 0.065
Detector resolution: 9 pixels mm-1	θmax = 25.4°, θmin = 3.4°
φ and ω scans to fill asymmetric unit	h = 0→22
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)	k = −10→11
Tmin = 0.991, Tmax = 0.998	l = −25→24
12501 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.0657P)2 + 0.3423P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
6668 reflections	Δρmax = 0.28 e Å−3
474 parameters	Δρmin = −0.14 e Å−3
548 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0055 (7)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.11545 (13)	0.6719 (2)	0.19762 (11)	0.0661 (6)
C2A	0.09371 (14)	0.8040 (3)	0.18252 (11)	0.0483 (6)
C3A	0.02414 (14)	0.8515 (3)	0.17983 (13)	0.0616 (7)
H3A	0.0107	0.9443	0.1682	0.074*
C4A	−0.02552 (16)	0.7579 (4)	0.19488 (15)	0.0771 (9)
H4A	−0.0732	0.7871	0.1935	0.092*
C5A	−0.00442 (19)	0.6229 (4)	0.21166 (16)	0.0817 (9)
H5A	−0.0368	0.5585	0.2226	0.098*
C6A	0.06588 (19)	0.5847 (3)	0.21201 (16)	0.0828 (10)
H6A	0.0801	0.4920	0.2230	0.099*
N7A	0.14984 (11)	0.8889 (2)	0.16925 (9)	0.0501 (6)
H7A	0.1889	0.8460	0.1652	0.060*
C8A	0.14887 (14)	1.0299 (3)	0.16219 (12)	0.0502 (7)
O9A	0.09855 (10)	1.10851 (19)	0.16598 (9)	0.0668 (5)
C10A	0.21768 (14)	1.0904 (3)	0.14793 (13)	0.0471 (6)
N11A	0.23810 (11)	1.0608 (2)	0.09302 (10)	0.0524 (6)
H11A	0.2816	1.0874	0.0919	0.063*
N12A	0.25797 (11)	1.1807 (2)	0.18870 (10)	0.0499 (5)
O13A	0.31518 (9)	1.24341 (18)	0.17334 (8)	0.0604 (5)
C14A	0.25051 (13)	1.2046 (3)	0.25341 (12)	0.0504 (7)
C15A	0.24581 (15)	1.3418 (3)	0.27317 (14)	0.0670 (8)
H15A	0.2466	1.4164	0.2449	0.080*
C16A	0.23996 (17)	1.3673 (4)	0.33547 (17)	0.0835 (9)
H16A	0.2365	1.4596	0.3494	0.100*
C17A	0.23921 (18)	1.2574 (5)	0.37671 (17)	0.0926 (11)
H17A	0.2343	1.2749	0.4184	0.111*
C18A	0.24558 (19)	1.1217 (4)	0.35712 (16)	0.0885 (10)
H18A	0.2458	1.0474	0.3858	0.106*
C19A	0.25170 (16)	1.0944 (3)	0.29510 (14)	0.0693 (8)
H19A	0.2566	1.0022	0.2818	0.083*
C20A	0.19658 (15)	0.9913 (3)	0.03686 (12)	0.0496 (7)
C21A	0.12171 (17)	1.0074 (3)	0.01520 (14)	0.0697 (8)
H21A	0.0962	1.0617	0.0388	0.084*
C22A	0.0844 (2)	0.9430 (4)	−0.04161 (17)	0.0858 (10)
H22A	0.0335	0.9522	−0.0554	0.103*
C23A	0.1207 (2)	0.8662 (4)	−0.07771 (16)	0.0854 (10)
H23A	0.0951	0.8253	−0.1165	0.102*
C24A	0.1954 (2)	0.8495 (3)	−0.05644 (16)	0.0801 (9)
H24A	0.2208	0.7974	−0.0810	0.096*
C25A	0.23329 (16)	0.9101 (3)	0.00149 (14)	0.0619 (7)
H25A	0.2837	0.8958	0.0165	0.074*
N1B	0.36559 (12)	0.1853 (2)	0.04201 (11)	0.0607 (6)
C2B	0.37519 (14)	0.3237 (3)	0.03646 (13)	0.0536 (7)
C3B	0.41689 (16)	0.3812 (3)	−0.00164 (15)	0.0749 (9)
H3B	0.4225	0.4785	−0.0042	0.090*
C4B	0.45036 (19)	0.2895 (4)	−0.03606 (17)	0.0926 (11)
H4B	0.4791	0.3245	−0.0624	0.111*
C5B	0.44097 (18)	0.1478 (4)	−0.03111 (17)	0.0851 (10)
H5B	0.4628	0.0846	−0.0541	0.102*
C6B	0.39919 (17)	0.1009 (3)	0.00806 (16)	0.0772 (9)
H6B	0.3935	0.0038	0.0116	0.093*
N7B	0.33914 (11)	0.4052 (2)	0.07475 (10)	0.0536 (6)
H7B	0.3210	0.3604	0.1023	0.064*
C8B	0.33054 (14)	0.5460 (3)	0.07221 (13)	0.0532 (7)
O9B	0.35086 (11)	0.62721 (19)	0.03605 (9)	0.0702 (6)
C10B	0.28999 (14)	0.6032 (3)	0.12011 (12)	0.0485 (7)
N11B	0.22196 (12)	0.5613 (2)	0.12126 (11)	0.0564 (6)
H11B	0.2086	0.5778	0.1564	0.068*
N12B	0.32199 (11)	0.7001 (2)	0.16157 (10)	0.0517 (6)
O13B	0.28421 (9)	0.76002 (18)	0.20063 (8)	0.0605 (5)
C14B	0.39782 (14)	0.7415 (3)	0.17218 (12)	0.0517 (7)
C15B	0.41339 (16)	0.8830 (3)	0.16710 (13)	0.0647 (8)
H15B	0.3756	0.9489	0.1561	0.078*
C16B	0.48549 (18)	0.9248 (4)	0.17850 (14)	0.0761 (9)
H16B	0.4965	1.0195	0.1743	0.091*
C17B	0.54132 (18)	0.8285 (5)	0.19598 (16)	0.0879 (10)
H17B	0.5901	0.8578	0.2038	0.105*
C18B	0.52519 (17)	0.6890 (4)	0.20198 (16)	0.0870 (10)
H18B	0.5632	0.6238	0.2143	0.104*
C19B	0.45248 (16)	0.6438 (3)	0.18974 (14)	0.0700 (8)
H19B	0.4414	0.5489	0.1935	0.084*
C25B	0.11891 (15)	0.4058 (3)	0.08793 (15)	0.0664 (8)
H25B	0.1223	0.3862	0.1314	0.080*
C24B	0.06318 (18)	0.3478 (3)	0.0403 (2)	0.0829 (10)
H24B	0.0276	0.2922	0.0518	0.099*
C23B	0.05954 (19)	0.3712 (3)	−0.0239 (2)	0.0888 (10)
H23B	0.0224	0.3300	−0.0559	0.107*
C22B	0.1108 (2)	0.4551 (4)	−0.04032 (18)	0.0916 (10)
H22B	0.1086	0.4700	−0.0839	0.110*
C21B	0.16563 (10)	0.51847 (18)	0.00578 (9)	0.0730 (8)
H21B	0.1996	0.5776	−0.0062	0.088*
C20B	0.16951 (10)	0.49270 (18)	0.07069 (9)	0.0549 (7)
O51	0.30526 (10)	0.73186 (18)	0.33354 (9)	0.119 (2)	0.586 (7)
H51	0.2985	0.7400	0.2941	0.178*	0.586 (7)
C51	0.38176 (10)	0.76316 (18)	0.36484 (9)	0.133 (4)	0.586 (7)
H51A	0.3863	0.8606	0.3777	0.200*	0.586 (7)
H51B	0.4117	0.7453	0.3351	0.200*	0.586 (7)
H51C	0.3978	0.7043	0.4024	0.200*	0.586 (7)
O52	0.35159 (10)	0.68397 (18)	0.34082 (9)	0.143 (7)	0.264 (7)
H52	0.3218	0.6949	0.3058	0.215*	0.264 (7)
C52	0.40649 (10)	0.80407 (18)	0.35212 (9)	0.171 (11)	0.264 (7)
H52A	0.3823	0.8894	0.3339	0.257*	0.264 (7)
H52B	0.4455	0.7825	0.3318	0.257*	0.264 (7)
H52C	0.4265	0.8165	0.3979	0.257*	0.264 (7)

	U11	U22	U33	U12	U13	U23
N1A	0.0653 (16)	0.0595 (15)	0.0838 (17)	−0.0015 (12)	0.0379 (13)	0.0106 (13)
C2A	0.0439 (16)	0.0569 (17)	0.0461 (15)	−0.0054 (13)	0.0151 (13)	−0.0046 (13)
C3A	0.0460 (17)	0.0653 (18)	0.074 (2)	−0.0036 (14)	0.0162 (15)	−0.0060 (15)
C4A	0.0511 (19)	0.093 (2)	0.092 (2)	−0.0105 (17)	0.0272 (17)	−0.0084 (19)
C5A	0.079 (2)	0.087 (2)	0.092 (2)	−0.0212 (19)	0.046 (2)	0.0020 (19)
C6A	0.084 (2)	0.073 (2)	0.106 (3)	−0.0031 (18)	0.051 (2)	0.0174 (18)
N7A	0.0426 (12)	0.0511 (14)	0.0604 (14)	0.0030 (10)	0.0201 (11)	−0.0014 (10)
C8A	0.0447 (17)	0.0561 (19)	0.0515 (16)	0.0012 (14)	0.0154 (13)	−0.0050 (13)
O9A	0.0513 (12)	0.0618 (12)	0.0934 (15)	0.0078 (10)	0.0297 (11)	0.0021 (10)
C10A	0.0442 (15)	0.0483 (15)	0.0520 (17)	0.0052 (13)	0.0180 (14)	0.0013 (13)
N11A	0.0459 (13)	0.0593 (13)	0.0557 (14)	−0.0028 (11)	0.0192 (12)	−0.0051 (11)
N12A	0.0442 (13)	0.0550 (13)	0.0519 (14)	−0.0028 (11)	0.0150 (11)	−0.0001 (11)
O13A	0.0474 (11)	0.0753 (12)	0.0620 (12)	−0.0126 (9)	0.0201 (9)	−0.0008 (9)
C14A	0.0388 (15)	0.0658 (18)	0.0468 (16)	−0.0034 (13)	0.0109 (12)	−0.0041 (14)
C15A	0.067 (2)	0.071 (2)	0.064 (2)	−0.0014 (15)	0.0177 (16)	−0.0080 (15)
C16A	0.077 (2)	0.100 (2)	0.074 (2)	−0.0006 (19)	0.0199 (19)	−0.026 (2)
C17A	0.078 (2)	0.148 (3)	0.053 (2)	−0.011 (2)	0.0190 (18)	−0.020 (2)
C18A	0.095 (3)	0.112 (3)	0.057 (2)	−0.012 (2)	0.0167 (19)	0.0110 (19)
C19A	0.079 (2)	0.0738 (19)	0.0555 (19)	−0.0043 (16)	0.0164 (16)	0.0039 (16)
C20A	0.0537 (17)	0.0462 (15)	0.0496 (16)	−0.0016 (13)	0.0142 (14)	0.0028 (13)
C21A	0.062 (2)	0.079 (2)	0.0645 (19)	0.0074 (16)	0.0091 (16)	−0.0059 (16)
C22A	0.073 (2)	0.104 (3)	0.071 (2)	−0.006 (2)	0.0009 (18)	0.0038 (19)
C23A	0.104 (3)	0.085 (2)	0.062 (2)	−0.023 (2)	0.009 (2)	−0.0073 (17)
C24A	0.111 (3)	0.070 (2)	0.067 (2)	−0.009 (2)	0.036 (2)	−0.0120 (16)
C25A	0.0666 (18)	0.0615 (17)	0.0625 (18)	−0.0035 (15)	0.0256 (15)	−0.0065 (15)
N1B	0.0583 (14)	0.0602 (15)	0.0723 (16)	0.0033 (11)	0.0325 (12)	−0.0032 (12)
C2B	0.0468 (16)	0.0611 (18)	0.0580 (17)	0.0001 (13)	0.0226 (14)	−0.0036 (14)
C3B	0.083 (2)	0.0724 (19)	0.088 (2)	−0.0073 (17)	0.0549 (19)	−0.0055 (17)
C4B	0.101 (3)	0.098 (3)	0.104 (3)	−0.008 (2)	0.072 (2)	−0.008 (2)
C5B	0.085 (2)	0.084 (2)	0.102 (3)	0.0070 (19)	0.054 (2)	−0.016 (2)
C6B	0.077 (2)	0.0695 (19)	0.101 (2)	0.0023 (17)	0.053 (2)	−0.0116 (18)
N7B	0.0574 (14)	0.0529 (15)	0.0600 (14)	−0.0003 (11)	0.0322 (12)	−0.0002 (11)
C8B	0.0508 (17)	0.0536 (19)	0.0573 (18)	−0.0028 (13)	0.0174 (14)	0.0028 (14)
O9B	0.0851 (14)	0.0621 (12)	0.0752 (14)	0.0014 (10)	0.0421 (12)	0.0134 (11)
C10B	0.0479 (17)	0.0466 (15)	0.0554 (17)	0.0021 (13)	0.0210 (14)	0.0038 (13)
N11B	0.0542 (15)	0.0570 (13)	0.0637 (15)	−0.0060 (11)	0.0257 (12)	−0.0043 (11)
N12B	0.0452 (14)	0.0566 (13)	0.0564 (14)	0.0059 (11)	0.0184 (12)	−0.0021 (11)
O13B	0.0508 (11)	0.0736 (12)	0.0607 (12)	0.0089 (9)	0.0205 (9)	−0.0089 (9)
C14B	0.0406 (16)	0.0643 (18)	0.0499 (16)	0.0023 (13)	0.0106 (13)	0.0018 (13)
C15B	0.0551 (18)	0.0648 (19)	0.070 (2)	−0.0006 (15)	0.0077 (15)	−0.0024 (15)
C16B	0.061 (2)	0.088 (2)	0.077 (2)	−0.0195 (18)	0.0125 (17)	−0.0088 (17)
C17B	0.050 (2)	0.130 (3)	0.081 (2)	−0.012 (2)	0.0120 (17)	0.002 (2)
C18B	0.049 (2)	0.117 (3)	0.089 (2)	0.0193 (19)	0.0043 (17)	0.013 (2)
C19B	0.0535 (19)	0.080 (2)	0.074 (2)	0.0140 (16)	0.0120 (16)	0.0121 (16)
C25B	0.0588 (19)	0.0571 (17)	0.086 (2)	−0.0057 (15)	0.0222 (17)	−0.0033 (16)
C24B	0.065 (2)	0.063 (2)	0.123 (3)	−0.0111 (16)	0.026 (2)	−0.012 (2)
C23B	0.069 (2)	0.081 (2)	0.105 (3)	−0.0058 (18)	0.002 (2)	−0.026 (2)
C22B	0.080 (2)	0.109 (3)	0.079 (2)	−0.009 (2)	0.009 (2)	−0.010 (2)
C21B	0.065 (2)	0.081 (2)	0.074 (2)	−0.0087 (16)	0.0184 (17)	0.0061 (17)
C20B	0.0456 (16)	0.0458 (15)	0.076 (2)	0.0007 (13)	0.0191 (15)	−0.0031 (14)
O51	0.155 (5)	0.139 (4)	0.066 (3)	−0.005 (4)	0.036 (3)	0.012 (3)
C51	0.128 (7)	0.143 (8)	0.117 (8)	−0.016 (7)	0.010 (6)	0.012 (6)
O52	0.099 (11)	0.143 (11)	0.180 (14)	−0.009 (8)	0.020 (9)	0.078 (10)
C52	0.24 (2)	0.134 (16)	0.15 (2)	−0.043 (14)	0.055 (17)	−0.091 (15)

N1A—C2A	1.331 (3)	C3B—H3B	0.9300
N1A—C6A	1.335 (4)	C4B—C5B	1.361 (4)
C2A—C3A	1.368 (3)	C4B—H4B	0.9300
C2A—N7A	1.408 (3)	C5B—C6B	1.353 (4)
C3A—C4A	1.380 (4)	C5B—H5B	0.9300
C3A—H3A	0.9300	C6B—H6B	0.9300
C4A—C5A	1.360 (4)	N7B—C8B	1.343 (3)
C4A—H4A	0.9300	N7B—H7B	0.8600
C5A—C6A	1.366 (4)	C8B—O9B	1.214 (3)
C5A—H5A	0.9300	C8B—C10B	1.516 (4)
C6A—H6A	0.9300	C10B—N12B	1.311 (3)
N7A—C8A	1.343 (3)	C10B—N11B	1.342 (3)
N7A—H7A	0.8600	N11B—C20B	1.422 (3)
C8A—O9A	1.221 (3)	N11B—H11B	0.8600
C8A—C10A	1.511 (3)	N12B—O13B	1.344 (2)
C10A—N12A	1.315 (3)	N12B—C14B	1.438 (3)
C10A—N11A	1.347 (3)	C14B—C19B	1.363 (4)
N11A—C20A	1.417 (3)	C14B—C15B	1.381 (4)
N11A—H11A	0.8600	C15B—C16B	1.372 (4)
N12A—O13A	1.336 (2)	C15B—H15B	0.9300
N12A—C14A	1.436 (3)	C16B—C17B	1.369 (4)
C14A—C19A	1.366 (4)	C16B—H16B	0.9300
C14A—C15A	1.376 (4)	C17B—C18B	1.369 (5)
C15A—C16A	1.379 (4)	C17B—H17B	0.9300
C15A—H15A	0.9300	C18B—C19B	1.391 (4)
C16A—C17A	1.364 (5)	C18B—H18B	0.9300
C16A—H16A	0.9300	C19B—H19B	0.9300
C17A—C18A	1.365 (5)	C25B—C20B	1.374 (3)
C17A—H17A	0.9300	C25B—C24B	1.377 (4)
C18A—C19A	1.378 (4)	C25B—H25B	0.9300
C18A—H18A	0.9300	C24B—C23B	1.368 (5)
C19A—H19A	0.9300	C24B—H24B	0.9300
C20A—C21A	1.374 (4)	C23B—C22B	1.358 (5)
C20A—C25A	1.375 (4)	C23B—H23B	0.9300
C21A—C22A	1.380 (4)	C22B—C21B	1.371 (4)
C21A—H21A	0.9300	C22B—H22B	0.9300
C22A—C23A	1.358 (4)	C21B—C20B	1.3870
C22A—H22A	0.9300	C21B—H21B	0.9300
C23A—C24A	1.372 (5)	O51—C51	1.4549
C23A—H23A	0.9300	O51—H51	0.8200
C24A—C25A	1.385 (4)	C51—H51A	0.9600
C24A—H24A	0.9300	C51—H51B	0.9600
C25A—H25A	0.9300	C51—H51C	0.9600
N1B—C2B	1.332 (3)	O52—C52	1.5130
N1B—C6B	1.336 (3)	O52—H52	0.8200
C2B—C3B	1.372 (4)	C52—H52A	0.9600
C2B—N7B	1.410 (3)	C52—H52B	0.9600
C3B—C4B	1.384 (4)	C52—H52C	0.9600
C2A—N1A—C6A	116.6 (2)	C5B—C4B—C3B	119.6 (3)
N1A—C2A—C3A	123.5 (2)	C5B—C4B—H4B	120.2
N1A—C2A—N7A	112.7 (2)	C3B—C4B—H4B	120.2
C3A—C2A—N7A	123.8 (2)	C6B—C5B—C4B	118.5 (3)
C2A—C3A—C4A	118.1 (3)	C6B—C5B—H5B	120.8
C2A—C3A—H3A	121.0	C4B—C5B—H5B	120.8
C4A—C3A—H3A	121.0	N1B—C6B—C5B	124.0 (3)
C5A—C4A—C3A	119.7 (3)	N1B—C6B—H6B	118.0
C5A—C4A—H4A	120.1	C5B—C6B—H6B	118.0
C3A—C4A—H4A	120.1	C8B—N7B—C2B	126.1 (2)
C4A—C5A—C6A	117.9 (3)	C8B—N7B—H7B	116.9
C4A—C5A—H5A	121.0	C2B—N7B—H7B	116.9
C6A—C5A—H5A	121.0	O9B—C8B—N7B	126.9 (2)
N1A—C6A—C5A	124.2 (3)	O9B—C8B—C10B	119.3 (2)
N1A—C6A—H6A	117.9	N7B—C8B—C10B	113.8 (2)
C5A—C6A—H6A	117.9	N12B—C10B—N11B	118.2 (2)
C8A—N7A—C2A	126.9 (2)	N12B—C10B—C8B	118.7 (2)
C8A—N7A—H7A	116.6	N11B—C10B—C8B	123.0 (2)
C2A—N7A—H7A	116.6	C10B—N11B—C20B	127.1 (2)
O9A—C8A—N7A	126.0 (2)	C10B—N11B—H11B	116.4
O9A—C8A—C10A	119.7 (2)	C20B—N11B—H11B	116.4
N7A—C8A—C10A	114.3 (2)	C10B—N12B—O13B	119.2 (2)
N12A—C10A—N11A	117.8 (2)	C10B—N12B—C14B	124.5 (2)
N12A—C10A—C8A	119.6 (2)	O13B—N12B—C14B	116.1 (2)
N11A—C10A—C8A	122.5 (2)	C19B—C14B—C15B	121.4 (3)
C10A—N11A—C20A	127.8 (2)	C19B—C14B—N12B	120.4 (2)
C10A—N11A—H11A	116.1	C15B—C14B—N12B	118.2 (2)
C20A—N11A—H11A	116.1	C16B—C15B—C14B	119.0 (3)
C10A—N12A—O13A	119.5 (2)	C16B—C15B—H15B	120.5
C10A—N12A—C14A	123.9 (2)	C14B—C15B—H15B	120.5
O13A—N12A—C14A	116.11 (19)	C17B—C16B—C15B	120.7 (3)
C19A—C14A—C15A	121.0 (3)	C17B—C16B—H16B	119.7
C19A—C14A—N12A	120.8 (2)	C15B—C16B—H16B	119.7
C15A—C14A—N12A	118.1 (2)	C18B—C17B—C16B	119.8 (3)
C14A—C15A—C16A	119.1 (3)	C18B—C17B—H17B	120.1
C14A—C15A—H15A	120.5	C16B—C17B—H17B	120.1
C16A—C15A—H15A	120.5	C17B—C18B—C19B	120.6 (3)
C17A—C16A—C15A	120.1 (3)	C17B—C18B—H18B	119.7
C17A—C16A—H16A	120.0	C19B—C18B—H18B	119.7
C15A—C16A—H16A	120.0	C14B—C19B—C18B	118.6 (3)
C16A—C17A—C18A	120.4 (3)	C14B—C19B—H19B	120.7
C16A—C17A—H17A	119.8	C18B—C19B—H19B	120.7
C18A—C17A—H17A	119.8	C20B—C25B—C24B	119.4 (3)
C17A—C18A—C19A	120.2 (3)	C20B—C25B—H25B	120.3
C17A—C18A—H18A	119.9	C24B—C25B—H25B	120.3
C19A—C18A—H18A	119.9	C23B—C24B—C25B	120.8 (3)
C14A—C19A—C18A	119.2 (3)	C23B—C24B—H24B	119.6
C14A—C19A—H19A	120.4	C25B—C24B—H24B	119.6
C18A—C19A—H19A	120.4	C22B—C23B—C24B	119.2 (3)
C21A—C20A—C25A	119.2 (3)	C22B—C23B—H23B	120.4
C21A—C20A—N11A	122.3 (2)	C24B—C23B—H23B	120.4
C25A—C20A—N11A	118.5 (2)	C23B—C22B—C21B	121.7 (3)
C20A—C21A—C22A	120.0 (3)	C23B—C22B—H22B	119.2
C20A—C21A—H21A	120.0	C21B—C22B—H22B	119.2
C22A—C21A—H21A	120.0	C22B—C21B—C20B	118.70 (19)
C23A—C22A—C21A	121.0 (3)	C22B—C21B—H21B	120.7
C23A—C22A—H22A	119.5	C20B—C21B—H21B	120.7
C21A—C22A—H22A	119.5	C25B—C20B—C21B	120.18 (15)
C22A—C23A—C24A	119.4 (3)	C25B—C20B—N11B	117.8 (2)
C22A—C23A—H23A	120.3	C21B—C20B—N11B	121.92 (11)
C24A—C23A—H23A	120.3	C51—O51—H51	109.5
C23A—C24A—C25A	120.1 (3)	O51—C51—H51A	109.5
C23A—C24A—H24A	119.9	O51—C51—H51B	109.5
C25A—C24A—H24A	119.9	H51A—C51—H51B	109.5
C20A—C25A—C24A	120.2 (3)	O51—C51—H51C	109.5
C20A—C25A—H25A	119.9	H51A—C51—H51C	109.5
C24A—C25A—H25A	119.9	H51B—C51—H51C	109.5
C2B—N1B—C6B	116.7 (2)	C52—O52—H52	109.5
N1B—C2B—C3B	123.5 (2)	O52—C52—H52A	109.5
N1B—C2B—N7B	113.1 (2)	O52—C52—H52B	109.5
C3B—C2B—N7B	123.4 (3)	H52A—C52—H52B	109.5
C2B—C3B—C4B	117.7 (3)	O52—C52—H52C	109.5
C2B—C3B—H3B	121.2	H52A—C52—H52C	109.5
C4B—C3B—H3B	121.2	H52B—C52—H52C	109.5
C6A—N1A—C2A—C3A	−1.5 (4)	C6B—N1B—C2B—C3B	0.1 (4)
C6A—N1A—C2A—N7A	178.9 (2)	C6B—N1B—C2B—N7B	−178.8 (2)
N1A—C2A—C3A—C4A	1.4 (4)	N1B—C2B—C3B—C4B	0.2 (4)
N7A—C2A—C3A—C4A	−179.1 (2)	N7B—C2B—C3B—C4B	179.0 (3)
C2A—C3A—C4A—C5A	−0.1 (4)	C2B—C3B—C4B—C5B	0.0 (5)
C3A—C4A—C5A—C6A	−0.9 (5)	C3B—C4B—C5B—C6B	−0.4 (5)
C2A—N1A—C6A—C5A	0.4 (5)	C2B—N1B—C6B—C5B	−0.5 (5)
C4A—C5A—C6A—N1A	0.8 (5)	C4B—C5B—C6B—N1B	0.7 (5)
N1A—C2A—N7A—C8A	−169.3 (2)	N1B—C2B—N7B—C8B	−170.1 (2)
C3A—C2A—N7A—C8A	11.1 (4)	C3B—C2B—N7B—C8B	11.0 (4)
C2A—N7A—C8A—O9A	−0.2 (4)	C2B—N7B—C8B—O9B	1.5 (4)
C2A—N7A—C8A—C10A	−179.8 (2)	C2B—N7B—C8B—C10B	−179.3 (2)
O9A—C8A—C10A—N12A	61.7 (3)	O9B—C8B—C10B—N12B	−57.1 (3)
N7A—C8A—C10A—N12A	−118.6 (2)	N7B—C8B—C10B—N12B	123.6 (2)
O9A—C8A—C10A—N11A	−115.0 (3)	O9B—C8B—C10B—N11B	121.4 (3)
N7A—C8A—C10A—N11A	64.7 (3)	N7B—C8B—C10B—N11B	−57.8 (3)
N12A—C10A—N11A—C20A	−166.1 (2)	N12B—C10B—N11B—C20B	159.7 (2)
C8A—C10A—N11A—C20A	10.6 (4)	C8B—C10B—N11B—C20B	−18.9 (4)
N11A—C10A—N12A—O13A	2.6 (3)	N11B—C10B—N12B—O13B	−4.1 (3)
C8A—C10A—N12A—O13A	−174.2 (2)	C8B—C10B—N12B—O13B	174.5 (2)
N11A—C10A—N12A—C14A	−169.2 (2)	N11B—C10B—N12B—C14B	171.1 (2)
C8A—C10A—N12A—C14A	13.9 (3)	C8B—C10B—N12B—C14B	−10.3 (4)
C10A—N12A—C14A—C19A	51.8 (3)	C10B—N12B—C14B—C19B	−56.8 (4)
O13A—N12A—C14A—C19A	−120.2 (3)	O13B—N12B—C14B—C19B	118.6 (3)
C10A—N12A—C14A—C15A	−131.3 (3)	C10B—N12B—C14B—C15B	126.2 (3)
O13A—N12A—C14A—C15A	56.6 (3)	O13B—N12B—C14B—C15B	−58.4 (3)
C19A—C14A—C15A—C16A	−2.0 (4)	C19B—C14B—C15B—C16B	1.6 (4)
N12A—C14A—C15A—C16A	−178.8 (2)	N12B—C14B—C15B—C16B	178.6 (2)
C14A—C15A—C16A—C17A	0.3 (4)	C14B—C15B—C16B—C17B	−1.4 (4)
C15A—C16A—C17A—C18A	1.2 (5)	C15B—C16B—C17B—C18B	0.2 (5)
C16A—C17A—C18A—C19A	−1.0 (5)	C16B—C17B—C18B—C19B	0.7 (5)
C15A—C14A—C19A—C18A	2.2 (4)	C15B—C14B—C19B—C18B	−0.7 (4)
N12A—C14A—C19A—C18A	179.0 (3)	N12B—C14B—C19B—C18B	−177.6 (3)
C17A—C18A—C19A—C14A	−0.7 (5)	C17B—C18B—C19B—C14B	−0.5 (5)
C10A—N11A—C20A—C21A	35.0 (4)	C20B—C25B—C24B—C23B	2.7 (4)
C10A—N11A—C20A—C25A	−147.9 (2)	C25B—C24B—C23B—C22B	−1.4 (5)
C25A—C20A—C21A—C22A	−0.3 (4)	C24B—C23B—C22B—C21B	−0.8 (5)
N11A—C20A—C21A—C22A	176.7 (2)	C23B—C22B—C21B—C20B	1.6 (4)
C20A—C21A—C22A—C23A	−1.7 (5)	C24B—C25B—C20B—C21B	−1.8 (3)
C21A—C22A—C23A—C24A	1.7 (5)	C24B—C25B—C20B—N11B	174.1 (2)
C22A—C23A—C24A—C25A	0.2 (5)	C22B—C21B—C20B—C25B	−0.3 (2)
C21A—C20A—C25A—C24A	2.3 (4)	C22B—C21B—C20B—N11B	−176.0 (3)
N11A—C20A—C25A—C24A	−174.9 (2)	C10B—N11B—C20B—C25B	152.2 (2)
C23A—C24A—C25A—C20A	−2.3 (4)	C10B—N11B—C20B—C21B	−32.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N7A—H7A···O13B	0.86	1.94	2.730 (3)	152
N11A—H11A···N1Bi	0.86	2.30	3.095 (3)	153
N11A—H11A···O13A	0.86	2.25	2.603 (3)	105
N7B—H7B···O13Aii	0.86	1.90	2.724 (3)	160
N11B—H11B···N1A	0.86	2.32	3.056 (3)	144
N11B—H11B···O13B	0.86	2.28	2.604 (3)	102
O51—H51···O13B	0.82	1.95	2.770 (3)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7A—H7A⋯O13B	0.86	1.94	2.730 (3)	152
N11A—H11A⋯N1Bi	0.86	2.30	3.095 (3)	153
N11A—H11A⋯O13A	0.86	2.25	2.603 (3)	105
N7B—H7B⋯O13Aii	0.86	1.90	2.724 (3)	160
N11B—H11B⋯N1A	0.86	2.32	3.056 (3)	144
N11B—H11B⋯O13B	0.86	2.28	2.604 (3)	102
O51—H51⋯O13B	0.82	1.95	2.770 (3)	179

Symmetry codes: (i) ; (ii) .