Chlorimipraminium picrate.

The title compound {systematic name: 3-chloro-5-[3-(dimethyl-amino)prop-yl]-10,11-dihydro-5H-dibenz[b,f]azepinium picrate}, C(19)H(24)ClN(2) (+)·C(6)H(2)N(3)O(7) (-), crystallizes with two independent cation-anion pairs in the asymmetric unit. The chlorimipraminium cation contains two benzene rings (one with a chloro substituent) fused to a V-shaped seven-membered azepine ring whose mean planes are separated by 61.1 (0) and 66.5 (8)° with a 3-(dimethyl-amino)propyl group extending away from the apex of this ring. In the picrate anion, the mean planes of the two o-NO(2) groups in each anion are twisted by 3.7 (2)/31.9 (3) and 31.3 (1)/11.4 (0)°, respectively, with respect to the mean plane of the six-membered benzene ring. The phenolate O atoms are bent slightly away from the mean plane of the benzene ring. The mean planes of the p-NO(2) groups are twisted by 6.6 (1) and 2.88°, respectively, from the mean plane of the benzene ring. The crystal packing features bifurcated N-H⋯(O,O) inter-molecular hydrogen-bond inter-action, which connects each cation-anion pair. Additional π-π ring and C-H⋯π weak inter-molecular inter-actions are also observed.

Related literature

For related structures, see: Bindya et al. (2007 ▶); Hallberg et al. (1984 ▶); Harrison, Bindya et al. (2007 ▶); Hallberg et al. (1984 ▶); Harrison, Sreevidya et al. (2007 ▶); Post et al. (1975 ▶); Post & Horn (1977 ▶); Swamy et al. (2007 ▶); Yathirajan et al. (2007 ▶). For obessive-compulsive disorder treatment, see: Albert et al. (2002 ▶). For pain disorder treatment, see: Cassano et al. (1988 ▶). For non-toxic cancer-therapeutic activity, see: Daley et al. (2005 ▶). For experimental anxiety in humans, see: Guimaraes et al. (1987 ▶). For quantum mechanical calculations, see: Becke (1988 ▶); Schmidt & Polik (2007 ▶); Frisch et al. (2004 ▶); Lee et al. (1988 ▶).

Experimental

Crystal data

C19H24ClN2 +·C6H2N3O7 −

M = 543.96

Triclinic,

a = 11.2252 (3) Å

b = 13.1514 (3) Å

c = 17.2787 (4) Å

α = 90.9414 (19)°

β = 91.1253 (19)°

γ = 100.4446 (19)°

V = 2507.55 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 110 K

0.47 × 0.41 × 0.15 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.918, T max = 0.969

32779 measured reflections

16481 independent reflections

10873 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.115

S = 0.98

16481 reflections

689 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.48 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶), enCIFer (Allen et al., 2004 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810000905/bt5128sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000905/bt5128Isup2.hkl

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

C19H24ClN2+·C6H2N3O7−	Z = 4
Mr = 543.96	F(000) = 1136
Triclinic, P1	Dx = 1.441 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.2252 (3) Å	Cell parameters from 14780 reflections
b = 13.1514 (3) Å	θ = 4.7–32.7°
c = 17.2787 (4) Å	µ = 0.21 mm−1
α = 90.9414 (19)°	T = 110 K
β = 91.1253 (19)°	Plate, yellow
γ = 100.4446 (19)°	0.47 × 0.41 × 0.15 mm
V = 2507.55 (10) Å3

Oxford Diffraction Gemini R CCD diffractometer	16481 independent reflections
Radiation source: Enhance (Mo) X-ray Source	10873 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 10.5081 pixels mm-1	θmax = 32.8°, θmin = 4.7°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −19→16
Tmin = 0.918, Tmax = 0.969	l = −23→26
32779 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0635P)2] where P = (Fo2 + 2Fc2)/3
16481 reflections	(Δ/σ)max < 0.001
689 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

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
Cl1	0.59334 (3)	0.87280 (3)	0.92251 (2)	0.03074 (9)
N1A	0.37421 (9)	0.86170 (8)	0.65507 (6)	0.0172 (2)
N2A	0.64917 (9)	0.73998 (8)	0.53424 (6)	0.0175 (2)
H2AB	0.6526	0.7035	0.5796	0.021*
C1A	0.39922 (10)	0.81199 (9)	0.72519 (7)	0.0166 (2)
C2A	0.47865 (10)	0.86207 (10)	0.78235 (7)	0.0183 (2)
H2AA	0.5199	0.9309	0.7755	0.022*
C3A	0.49670 (11)	0.81002 (10)	0.84951 (7)	0.0198 (3)
C4A	0.43734 (11)	0.71005 (10)	0.86195 (7)	0.0200 (3)
H4AA	0.4498	0.6760	0.9087	0.024*
C5A	0.35871 (11)	0.66092 (10)	0.80371 (8)	0.0210 (3)
H5AA	0.3167	0.5925	0.8114	0.025*
C6A	0.34025 (11)	0.70941 (10)	0.73483 (7)	0.0184 (2)
C7A	0.25976 (12)	0.65622 (10)	0.67027 (8)	0.0240 (3)
H7AA	0.2404	0.5812	0.6802	0.029*
H7AB	0.3038	0.6655	0.6211	0.029*
C8A	0.14237 (12)	0.69788 (11)	0.66183 (9)	0.0288 (3)
H8AA	0.0972	0.6631	0.6160	0.035*
H8AB	0.0931	0.6765	0.7077	0.035*
C9A	0.14981 (11)	0.81328 (10)	0.65337 (7)	0.0212 (3)
C10A	0.03832 (12)	0.84621 (11)	0.64822 (8)	0.0265 (3)
H10A	−0.0339	0.7961	0.6512	0.032*
C11A	0.02888 (12)	0.94905 (12)	0.63898 (8)	0.0273 (3)
H11A	−0.0484	0.9685	0.6342	0.033*
C12A	0.13302 (12)	1.02253 (11)	0.63690 (8)	0.0246 (3)
H12A	0.1281	1.0934	0.6314	0.030*
C13A	0.24533 (11)	0.99277 (10)	0.64291 (7)	0.0201 (3)
H13A	0.3168	1.0440	0.6420	0.024*
C14A	0.25533 (11)	0.88889 (10)	0.65020 (7)	0.0171 (2)
C15A	0.47414 (11)	0.93650 (10)	0.62436 (8)	0.0192 (2)
H15A	0.4982	0.9939	0.6625	0.023*
H15B	0.4462	0.9658	0.5763	0.023*
C16A	0.58398 (11)	0.88708 (10)	0.60687 (7)	0.0189 (2)
H16A	0.6517	0.9410	0.5906	0.023*
H16B	0.6103	0.8554	0.6543	0.023*
C17A	0.55383 (11)	0.80490 (10)	0.54323 (7)	0.0191 (2)
H17A	0.4761	0.7595	0.5548	0.023*
H17B	0.5429	0.8390	0.4936	0.023*
C18A	0.77140 (11)	0.80309 (11)	0.52275 (8)	0.0268 (3)
H18A	0.7975	0.8448	0.5696	0.040*
H18B	0.7680	0.8488	0.4788	0.040*
H18C	0.8292	0.7572	0.5122	0.040*
C19A	0.61616 (13)	0.66325 (11)	0.46961 (7)	0.0249 (3)
H19A	0.5368	0.6208	0.4790	0.037*
H19B	0.6772	0.6188	0.4664	0.037*
H19C	0.6127	0.6996	0.4208	0.037*
Cl2	0.19710 (4)	0.83645 (3)	0.44656 (2)	0.03975 (10)
N1B	−0.00504 (8)	0.84031 (8)	0.17770 (6)	0.0164 (2)
N2B	0.16727 (9)	0.76659 (8)	0.02222 (6)	0.0194 (2)
H2BB	0.1600	0.7376	0.0710	0.023*
C1B	−0.00482 (11)	0.79100 (9)	0.25044 (7)	0.0179 (2)
C2B	0.08559 (11)	0.82856 (10)	0.30604 (7)	0.0196 (2)
H2BA	0.1479	0.8848	0.2941	0.024*
C3B	0.08492 (13)	0.78428 (11)	0.37833 (8)	0.0257 (3)
C4B	−0.00406 (14)	0.70222 (12)	0.39755 (9)	0.0322 (3)
H4BA	−0.0046	0.6725	0.4473	0.039*
C5B	−0.09206 (13)	0.66473 (11)	0.34232 (9)	0.0307 (3)
H5BA	−0.1533	0.6081	0.3552	0.037*
C6B	−0.09587 (11)	0.70576 (10)	0.26812 (9)	0.0242 (3)
C7B	−0.19630 (13)	0.65203 (12)	0.21395 (10)	0.0354 (4)
H7BA	−0.2743	0.6529	0.2395	0.043*
H7BB	−0.1874	0.5787	0.2086	0.043*
C8B	−0.20590 (12)	0.69393 (11)	0.13257 (9)	0.0299 (3)
H8BA	−0.1331	0.6859	0.1033	0.036*
H8BB	−0.2777	0.6536	0.1050	0.036*
C9B	−0.21672 (11)	0.80566 (10)	0.13599 (8)	0.0224 (3)
C10B	−0.32578 (12)	0.83958 (12)	0.12103 (8)	0.0283 (3)
H10B	−0.3956	0.7910	0.1050	0.034*
C11B	−0.33334 (12)	0.94331 (12)	0.12930 (8)	0.0286 (3)
H11B	−0.4079	0.9655	0.1188	0.034*
C12B	−0.23241 (12)	1.01431 (11)	0.15281 (7)	0.0236 (3)
H12B	−0.2380	1.0852	0.1587	0.028*
C13B	−0.12244 (11)	0.98269 (10)	0.16791 (7)	0.0181 (2)
H13B	−0.0529	1.0319	0.1833	0.022*
C14B	−0.11529 (10)	0.87815 (10)	0.16026 (7)	0.0176 (2)
C15B	0.10829 (10)	0.90796 (9)	0.15678 (7)	0.0160 (2)
H15C	0.1776	0.8734	0.1689	0.019*
H15D	0.1187	0.9729	0.1880	0.019*
C16B	0.10798 (11)	0.93317 (10)	0.07102 (7)	0.0191 (2)
H16C	0.0473	0.9779	0.0615	0.023*
H16D	0.1884	0.9735	0.0586	0.023*
C17B	0.08041 (11)	0.84068 (10)	0.01625 (7)	0.0201 (3)
H17C	−0.0022	0.8027	0.0263	0.024*
H17D	0.0804	0.8658	−0.0375	0.024*
C18B	0.29610 (11)	0.81780 (11)	0.01351 (8)	0.0245 (3)
H18D	0.3482	0.7655	0.0146	0.037*
H18E	0.3199	0.8679	0.0561	0.037*
H18F	0.3049	0.8536	−0.0359	0.037*
C19B	0.13262 (14)	0.68120 (11)	−0.03663 (8)	0.0293 (3)
H19D	0.0488	0.6468	−0.0287	0.044*
H19E	0.1868	0.6310	−0.0311	0.044*
H19F	0.1396	0.7098	−0.0887	0.044*
O1C	0.26076 (8)	0.70245 (7)	0.15382 (5)	0.0229 (2)
O21C	0.38889 (9)	0.86117 (7)	0.24018 (6)	0.0298 (2)
O22C	0.50236 (9)	0.79895 (8)	0.32264 (7)	0.0370 (3)
O41C	0.27695 (10)	0.55178 (8)	0.49309 (5)	0.0319 (2)
O42C	0.12957 (9)	0.43593 (8)	0.44634 (6)	0.0346 (3)
O61C	−0.00593 (11)	0.44920 (9)	0.18672 (7)	0.0511 (4)
O62C	0.04994 (9)	0.58148 (9)	0.11703 (6)	0.0384 (3)
N2C	0.41012 (9)	0.79142 (8)	0.28158 (7)	0.0214 (2)
N4C	0.20810 (10)	0.51373 (9)	0.43944 (6)	0.0229 (2)
N6C	0.05988 (10)	0.53218 (9)	0.17559 (6)	0.0225 (2)
C1C	0.24304 (10)	0.66219 (9)	0.21843 (7)	0.0156 (2)
C2C	0.31920 (10)	0.69712 (9)	0.28621 (7)	0.0161 (2)
C3C	0.31107 (11)	0.64889 (9)	0.35594 (7)	0.0174 (2)
H3CA	0.3660	0.6739	0.3974	0.021*
C4C	0.22078 (11)	0.56251 (9)	0.36500 (7)	0.0171 (2)
C5C	0.14014 (10)	0.52518 (10)	0.30518 (7)	0.0175 (2)
H5CA	0.0786	0.4665	0.3126	0.021*
C6C	0.14961 (10)	0.57354 (9)	0.23489 (7)	0.0168 (2)
O1D	0.71604 (8)	0.69222 (7)	0.67815 (5)	0.0226 (2)
O21D	0.52660 (10)	0.56347 (9)	0.61786 (6)	0.0393 (3)
O22D	0.43317 (9)	0.44269 (9)	0.68675 (6)	0.0362 (3)
O41D	0.53373 (9)	0.39608 (8)	0.94767 (6)	0.0316 (2)
O42D	0.68754 (10)	0.49588 (8)	1.00391 (6)	0.0322 (2)
O61D	0.91601 (11)	0.78149 (10)	0.86413 (8)	0.0555 (4)
O62D	0.81134 (9)	0.84577 (8)	0.77794 (6)	0.0337 (2)
N2D	0.51250 (9)	0.51864 (8)	0.67940 (6)	0.0176 (2)
N4D	0.61854 (10)	0.47077 (9)	0.94774 (6)	0.0232 (2)
N6D	0.83039 (10)	0.77441 (9)	0.81814 (7)	0.0266 (3)
C1D	0.68478 (10)	0.64639 (9)	0.73884 (7)	0.0149 (2)
C2D	0.59071 (10)	0.55516 (9)	0.74548 (7)	0.0152 (2)
C3D	0.56982 (10)	0.49945 (9)	0.81231 (7)	0.0167 (2)
H3DA	0.5083	0.4395	0.8129	0.020*
C4D	0.63868 (11)	0.53121 (10)	0.87829 (7)	0.0176 (2)
C5D	0.72585 (11)	0.62116 (10)	0.87969 (7)	0.0198 (3)
H5DA	0.7717	0.6434	0.9256	0.024*
C6D	0.74406 (11)	0.67694 (9)	0.81332 (7)	0.0175 (2)

	U11	U22	U33	U12	U13	U23
Cl1	0.02852 (17)	0.0392 (2)	0.02166 (16)	−0.00019 (14)	−0.00720 (13)	−0.00441 (14)
N1A	0.0177 (5)	0.0158 (5)	0.0173 (5)	0.0004 (4)	0.0016 (4)	0.0029 (4)
N2A	0.0208 (5)	0.0189 (5)	0.0131 (5)	0.0044 (4)	−0.0010 (4)	0.0026 (4)
C1A	0.0173 (5)	0.0164 (6)	0.0162 (6)	0.0032 (4)	0.0016 (4)	0.0000 (5)
C2A	0.0183 (5)	0.0164 (6)	0.0195 (6)	0.0013 (4)	0.0029 (5)	0.0007 (5)
C3A	0.0162 (5)	0.0272 (7)	0.0160 (6)	0.0042 (5)	−0.0005 (5)	−0.0044 (5)
C4A	0.0223 (6)	0.0225 (7)	0.0167 (6)	0.0069 (5)	0.0033 (5)	0.0039 (5)
C5A	0.0236 (6)	0.0162 (6)	0.0234 (6)	0.0039 (5)	0.0032 (5)	0.0030 (5)
C6A	0.0195 (6)	0.0156 (6)	0.0200 (6)	0.0030 (4)	−0.0003 (5)	−0.0010 (5)
C7A	0.0299 (7)	0.0157 (6)	0.0237 (7)	−0.0018 (5)	−0.0039 (5)	−0.0019 (5)
C8A	0.0281 (7)	0.0219 (7)	0.0329 (8)	−0.0043 (5)	−0.0065 (6)	0.0024 (6)
C9A	0.0229 (6)	0.0211 (7)	0.0180 (6)	0.0006 (5)	−0.0047 (5)	0.0009 (5)
C10A	0.0201 (6)	0.0334 (8)	0.0243 (7)	0.0004 (5)	−0.0031 (5)	0.0007 (6)
C11A	0.0204 (6)	0.0353 (8)	0.0268 (7)	0.0071 (5)	−0.0003 (5)	−0.0043 (6)
C12A	0.0311 (7)	0.0250 (7)	0.0198 (6)	0.0099 (5)	0.0036 (5)	0.0014 (5)
C13A	0.0229 (6)	0.0200 (7)	0.0170 (6)	0.0023 (5)	0.0043 (5)	0.0011 (5)
C14A	0.0200 (6)	0.0190 (6)	0.0115 (5)	0.0017 (4)	−0.0003 (4)	0.0007 (4)
C15A	0.0216 (6)	0.0156 (6)	0.0197 (6)	0.0008 (5)	0.0048 (5)	0.0028 (5)
C16A	0.0187 (6)	0.0174 (6)	0.0196 (6)	0.0006 (4)	0.0024 (5)	0.0009 (5)
C17A	0.0186 (6)	0.0208 (6)	0.0188 (6)	0.0058 (5)	0.0007 (5)	0.0010 (5)
C18A	0.0209 (6)	0.0325 (8)	0.0274 (7)	0.0048 (5)	0.0054 (5)	0.0055 (6)
C19A	0.0344 (7)	0.0273 (7)	0.0156 (6)	0.0134 (6)	−0.0047 (5)	−0.0041 (5)
Cl2	0.0620 (3)	0.0449 (2)	0.01714 (16)	0.02406 (19)	−0.00841 (16)	−0.00375 (15)
N1B	0.0146 (4)	0.0161 (5)	0.0179 (5)	0.0004 (4)	0.0016 (4)	0.0033 (4)
N2B	0.0232 (5)	0.0235 (6)	0.0120 (5)	0.0056 (4)	−0.0003 (4)	0.0028 (4)
C1B	0.0195 (6)	0.0161 (6)	0.0194 (6)	0.0061 (4)	0.0060 (5)	0.0030 (5)
C2B	0.0233 (6)	0.0197 (6)	0.0180 (6)	0.0090 (5)	0.0051 (5)	0.0027 (5)
C3B	0.0352 (7)	0.0300 (8)	0.0170 (6)	0.0187 (6)	0.0037 (5)	0.0016 (5)
C4B	0.0474 (9)	0.0335 (8)	0.0230 (7)	0.0240 (7)	0.0169 (7)	0.0138 (6)
C5B	0.0317 (7)	0.0229 (7)	0.0403 (9)	0.0096 (6)	0.0197 (7)	0.0139 (6)
C6B	0.0230 (6)	0.0173 (7)	0.0336 (8)	0.0052 (5)	0.0100 (6)	0.0055 (6)
C7B	0.0254 (7)	0.0231 (8)	0.0546 (10)	−0.0053 (6)	0.0054 (7)	0.0073 (7)
C8B	0.0202 (6)	0.0238 (8)	0.0424 (9)	−0.0036 (5)	0.0005 (6)	−0.0068 (6)
C9B	0.0183 (6)	0.0244 (7)	0.0235 (7)	0.0012 (5)	0.0000 (5)	−0.0034 (5)
C10B	0.0185 (6)	0.0394 (9)	0.0258 (7)	0.0027 (5)	−0.0026 (5)	−0.0026 (6)
C11B	0.0208 (6)	0.0433 (9)	0.0234 (7)	0.0107 (6)	−0.0020 (5)	0.0014 (6)
C12B	0.0300 (7)	0.0271 (7)	0.0161 (6)	0.0115 (5)	0.0018 (5)	0.0034 (5)
C13B	0.0199 (6)	0.0218 (7)	0.0127 (5)	0.0037 (5)	0.0005 (4)	0.0022 (5)
C14B	0.0165 (5)	0.0216 (6)	0.0146 (5)	0.0028 (4)	0.0003 (4)	0.0002 (5)
C15B	0.0146 (5)	0.0160 (6)	0.0163 (6)	−0.0003 (4)	−0.0001 (4)	0.0005 (4)
C16B	0.0192 (6)	0.0208 (7)	0.0179 (6)	0.0043 (5)	0.0026 (5)	0.0052 (5)
C17B	0.0185 (6)	0.0280 (7)	0.0147 (6)	0.0067 (5)	−0.0012 (5)	0.0026 (5)
C18B	0.0202 (6)	0.0338 (8)	0.0209 (6)	0.0079 (5)	0.0033 (5)	0.0085 (6)
C19B	0.0419 (8)	0.0279 (8)	0.0187 (6)	0.0086 (6)	−0.0052 (6)	−0.0038 (5)
O1C	0.0265 (5)	0.0232 (5)	0.0175 (4)	0.0002 (4)	−0.0041 (4)	0.0073 (4)
O21C	0.0333 (5)	0.0177 (5)	0.0361 (6)	−0.0010 (4)	−0.0094 (4)	0.0087 (4)
O22C	0.0277 (5)	0.0283 (6)	0.0505 (7)	−0.0049 (4)	−0.0219 (5)	0.0079 (5)
O41C	0.0491 (6)	0.0320 (6)	0.0153 (5)	0.0098 (5)	−0.0084 (4)	0.0002 (4)
O42C	0.0370 (6)	0.0373 (6)	0.0268 (5)	−0.0023 (5)	0.0037 (4)	0.0141 (5)
O61C	0.0588 (7)	0.0406 (7)	0.0383 (7)	−0.0310 (6)	−0.0217 (6)	0.0118 (6)
O62C	0.0384 (6)	0.0463 (7)	0.0242 (5)	−0.0086 (5)	−0.0122 (5)	0.0095 (5)
N2C	0.0214 (5)	0.0155 (5)	0.0260 (6)	0.0004 (4)	−0.0055 (4)	0.0011 (4)
N4C	0.0302 (6)	0.0240 (6)	0.0162 (5)	0.0088 (5)	0.0026 (4)	0.0034 (4)
N6C	0.0234 (5)	0.0232 (6)	0.0186 (5)	−0.0008 (4)	−0.0040 (4)	−0.0011 (4)
C1C	0.0176 (5)	0.0139 (6)	0.0155 (6)	0.0035 (4)	−0.0023 (4)	0.0005 (4)
C2C	0.0165 (5)	0.0124 (6)	0.0191 (6)	0.0019 (4)	−0.0026 (4)	0.0002 (4)
C3C	0.0199 (6)	0.0164 (6)	0.0168 (6)	0.0070 (4)	−0.0050 (5)	−0.0025 (5)
C4C	0.0219 (6)	0.0176 (6)	0.0129 (5)	0.0066 (5)	0.0006 (4)	0.0023 (4)
C5C	0.0174 (5)	0.0161 (6)	0.0186 (6)	0.0019 (4)	0.0009 (5)	0.0006 (5)
C6C	0.0177 (5)	0.0166 (6)	0.0158 (6)	0.0026 (4)	−0.0039 (4)	−0.0011 (4)
O1D	0.0234 (4)	0.0242 (5)	0.0174 (4)	−0.0037 (4)	−0.0030 (4)	0.0060 (4)
O21D	0.0484 (6)	0.0392 (7)	0.0202 (5)	−0.0180 (5)	−0.0144 (5)	0.0097 (5)
O22D	0.0331 (5)	0.0403 (6)	0.0244 (5)	−0.0216 (4)	−0.0022 (4)	−0.0009 (5)
O41D	0.0382 (6)	0.0271 (6)	0.0280 (5)	0.0007 (4)	0.0044 (4)	0.0116 (4)
O42D	0.0480 (6)	0.0337 (6)	0.0167 (5)	0.0121 (5)	−0.0057 (4)	0.0041 (4)
O61D	0.0492 (7)	0.0487 (8)	0.0557 (8)	−0.0222 (6)	−0.0348 (6)	0.0102 (6)
O62D	0.0456 (6)	0.0176 (5)	0.0339 (6)	−0.0047 (4)	−0.0033 (5)	0.0010 (4)
N2D	0.0169 (5)	0.0190 (5)	0.0158 (5)	0.0004 (4)	−0.0005 (4)	−0.0022 (4)
N4D	0.0316 (6)	0.0240 (6)	0.0163 (5)	0.0104 (5)	0.0027 (5)	0.0046 (4)
N6D	0.0288 (6)	0.0232 (6)	0.0230 (6)	−0.0071 (5)	−0.0044 (5)	−0.0022 (5)
C1D	0.0153 (5)	0.0146 (6)	0.0150 (5)	0.0034 (4)	−0.0020 (4)	0.0001 (4)
C2D	0.0167 (5)	0.0147 (6)	0.0139 (5)	0.0022 (4)	−0.0019 (4)	−0.0020 (4)
C3D	0.0185 (5)	0.0131 (6)	0.0183 (6)	0.0022 (4)	0.0026 (5)	0.0007 (5)
C4D	0.0229 (6)	0.0170 (6)	0.0140 (5)	0.0061 (5)	0.0010 (5)	0.0036 (5)
C5D	0.0221 (6)	0.0217 (7)	0.0160 (6)	0.0055 (5)	−0.0047 (5)	−0.0023 (5)
C6D	0.0188 (5)	0.0149 (6)	0.0174 (6)	−0.0005 (4)	−0.0025 (5)	−0.0006 (5)

Cl1—C3A	1.7427 (13)	C7B—C8B	1.528 (2)
N1A—C1A	1.4329 (15)	C7B—H7BA	0.9900
N1A—C14A	1.4441 (15)	C7B—H7BB	0.9900
N1A—C15A	1.4656 (15)	C8B—C9B	1.496 (2)
N2A—C19A	1.4879 (16)	C8B—H8BA	0.9900
N2A—C18A	1.4879 (16)	C8B—H8BB	0.9900
N2A—C17A	1.4940 (15)	C9B—C10B	1.3979 (18)
N2A—H2AB	0.9300	C9B—C14B	1.3985 (17)
C1A—C2A	1.3912 (17)	C10B—C11B	1.387 (2)
C1A—C6A	1.4050 (17)	C10B—H10B	0.9500
C2A—C3A	1.3870 (17)	C11B—C12B	1.381 (2)
C2A—H2AA	0.9500	C11B—H11B	0.9500
C3A—C4A	1.3841 (18)	C12B—C13B	1.3935 (17)
C4A—C5A	1.3950 (18)	C12B—H12B	0.9500
C4A—H4AA	0.9500	C13B—C14B	1.3959 (18)
C5A—C6A	1.3890 (17)	C13B—H13B	0.9500
C5A—H5AA	0.9500	C15B—C16B	1.5238 (17)
C6A—C7A	1.5019 (17)	C15B—H15C	0.9900
C7A—C8A	1.5214 (19)	C15B—H15D	0.9900
C7A—H7AA	0.9900	C16B—C17B	1.5117 (19)
C7A—H7AB	0.9900	C16B—H16C	0.9900
C8A—C9A	1.5145 (19)	C16B—H16D	0.9900
C8A—H8AA	0.9900	C17B—H17C	0.9900
C8A—H8AB	0.9900	C17B—H17D	0.9900
C9A—C10A	1.3983 (19)	C18B—H18D	0.9800
C9A—C14A	1.4043 (17)	C18B—H18E	0.9800
C10A—C11A	1.387 (2)	C18B—H18F	0.9800
C10A—H10A	0.9500	C19B—H19D	0.9800
C11A—C12A	1.3765 (19)	C19B—H19E	0.9800
C11A—H11A	0.9500	C19B—H19F	0.9800
C12A—C13A	1.3887 (18)	O1C—C1C	1.2474 (14)
C12A—H12A	0.9500	O21C—N2C	1.2265 (13)
C13A—C14A	1.3984 (18)	O22C—N2C	1.2316 (13)
C13A—H13A	0.9500	O41C—N4C	1.2343 (14)
C15A—C16A	1.5273 (17)	O42C—N4C	1.2326 (14)
C15A—H15A	0.9900	O61C—N6C	1.2221 (14)
C15A—H15B	0.9900	O62C—N6C	1.2248 (14)
C16A—C17A	1.5182 (18)	N2C—C2C	1.4606 (15)
C16A—H16A	0.9900	N4C—C4C	1.4447 (15)
C16A—H16B	0.9900	N6C—C6C	1.4501 (15)
C17A—H17A	0.9900	C1C—C2C	1.4540 (16)
C17A—H17B	0.9900	C1C—C6C	1.4558 (16)
C18A—H18A	0.9800	C2C—C3C	1.3678 (17)
C18A—H18B	0.9800	C3C—C4C	1.3917 (17)
C18A—H18C	0.9800	C3C—H3CA	0.9500
C19A—H19A	0.9800	C4C—C5C	1.3836 (16)
C19A—H19B	0.9800	C5C—C6C	1.3773 (16)
C19A—H19C	0.9800	C5C—H5CA	0.9500
Cl2—C3B	1.7459 (15)	O1D—C1D	1.2429 (14)
N1B—C1B	1.4240 (15)	O21D—N2D	1.2234 (13)
N1B—C14B	1.4435 (15)	O22D—N2D	1.2218 (13)
N1B—C15B	1.4692 (14)	O41D—N4D	1.2377 (14)
N2B—C18B	1.4920 (16)	O42D—N4D	1.2323 (14)
N2B—C19B	1.4950 (17)	O61D—N6D	1.2244 (14)
N2B—C17B	1.5016 (16)	O62D—N6D	1.2236 (15)
N2B—H2BB	0.9300	N2D—C2D	1.4474 (14)
C1B—C2B	1.4004 (17)	N4D—C4D	1.4491 (15)
C1B—C6B	1.4150 (17)	N6D—C6D	1.4602 (16)
C2B—C3B	1.3864 (17)	C1D—C6D	1.4534 (16)
C2B—H2BA	0.9500	C1D—C2D	1.4552 (16)
C3B—C4B	1.381 (2)	C2D—C3D	1.3789 (16)
C4B—C5B	1.379 (2)	C3D—C4D	1.3800 (17)
C4B—H4BA	0.9500	C3D—H3DA	0.9500
C5B—C6B	1.402 (2)	C4D—C5D	1.3913 (18)
C5B—H5BA	0.9500	C5D—C6D	1.3703 (17)
C6B—C7B	1.515 (2)	C5D—H5DA	0.9500
C1A—N1A—C14A	114.64 (10)	C6B—C7B—C8B	118.55 (11)
C1A—N1A—C15A	116.51 (10)	C6B—C7B—H7BA	107.7
C14A—N1A—C15A	116.45 (10)	C8B—C7B—H7BA	107.7
C19A—N2A—C18A	110.55 (10)	C6B—C7B—H7BB	107.7
C19A—N2A—C17A	110.57 (9)	C8B—C7B—H7BB	107.7
C18A—N2A—C17A	112.47 (10)	H7BA—C7B—H7BB	107.1
C19A—N2A—H2AB	107.7	C9B—C8B—C7B	110.77 (13)
C18A—N2A—H2AB	107.7	C9B—C8B—H8BA	109.5
C17A—N2A—H2AB	107.7	C7B—C8B—H8BA	109.5
C2A—C1A—C6A	120.33 (11)	C9B—C8B—H8BB	109.5
C2A—C1A—N1A	122.10 (11)	C7B—C8B—H8BB	109.5
C6A—C1A—N1A	117.57 (11)	H8BA—C8B—H8BB	108.1
C3A—C2A—C1A	119.05 (11)	C10B—C9B—C14B	118.76 (13)
C3A—C2A—H2AA	120.5	C10B—C9B—C8B	122.75 (12)
C1A—C2A—H2AA	120.5	C14B—C9B—C8B	118.35 (11)
C4A—C3A—C2A	122.16 (11)	C11B—C10B—C9B	120.80 (13)
C4A—C3A—Cl1	118.28 (10)	C11B—C10B—H10B	119.6
C2A—C3A—Cl1	119.53 (10)	C9B—C10B—H10B	119.6
C3A—C4A—C5A	117.92 (11)	C12B—C11B—C10B	119.94 (12)
C3A—C4A—H4AA	121.0	C12B—C11B—H11B	120.0
C5A—C4A—H4AA	121.0	C10B—C11B—H11B	120.0
C6A—C5A—C4A	121.75 (12)	C11B—C12B—C13B	120.47 (13)
C6A—C5A—H5AA	119.1	C11B—C12B—H12B	119.8
C4A—C5A—H5AA	119.1	C13B—C12B—H12B	119.8
C5A—C6A—C1A	118.74 (11)	C12B—C13B—C14B	119.50 (12)
C5A—C6A—C7A	122.46 (11)	C12B—C13B—H13B	120.2
C1A—C6A—C7A	118.80 (11)	C14B—C13B—H13B	120.2
C6A—C7A—C8A	112.37 (12)	C13B—C14B—C9B	120.51 (11)
C6A—C7A—H7AA	109.1	C13B—C14B—N1B	122.00 (11)
C8A—C7A—H7AA	109.1	C9B—C14B—N1B	117.48 (11)
C6A—C7A—H7AB	109.1	N1B—C15B—C16B	111.24 (9)
C8A—C7A—H7AB	109.1	N1B—C15B—H15C	109.4
H7AA—C7A—H7AB	107.9	C16B—C15B—H15C	109.4
C9A—C8A—C7A	118.47 (11)	N1B—C15B—H15D	109.4
C9A—C8A—H8AA	107.7	C16B—C15B—H15D	109.4
C7A—C8A—H8AA	107.7	H15C—C15B—H15D	108.0
C9A—C8A—H8AB	107.7	C17B—C16B—C15B	115.30 (10)
C7A—C8A—H8AB	107.7	C17B—C16B—H16C	108.4
H8AA—C8A—H8AB	107.1	C15B—C16B—H16C	108.5
C10A—C9A—C14A	117.66 (12)	C17B—C16B—H16D	108.5
C10A—C9A—C8A	115.25 (12)	C15B—C16B—H16D	108.4
C14A—C9A—C8A	127.09 (12)	H16C—C16B—H16D	107.5
C11A—C10A—C9A	122.66 (13)	N2B—C17B—C16B	114.80 (10)
C11A—C10A—H10A	118.7	N2B—C17B—H17C	108.6
C9A—C10A—H10A	118.7	C16B—C17B—H17C	108.6
C12A—C11A—C10A	119.06 (12)	N2B—C17B—H17D	108.6
C12A—C11A—H11A	120.5	C16B—C17B—H17D	108.6
C10A—C11A—H11A	120.5	H17C—C17B—H17D	107.5
C11A—C12A—C13A	119.82 (13)	N2B—C18B—H18D	109.5
C11A—C12A—H12A	120.1	N2B—C18B—H18E	109.5
C13A—C12A—H12A	120.1	H18D—C18B—H18E	109.5
C12A—C13A—C14A	121.31 (12)	N2B—C18B—H18F	109.5
C12A—C13A—H13A	119.3	H18D—C18B—H18F	109.5
C14A—C13A—H13A	119.3	H18E—C18B—H18F	109.5
C13A—C14A—C9A	119.45 (11)	N2B—C19B—H19D	109.5
C13A—C14A—N1A	119.22 (11)	N2B—C19B—H19E	109.5
C9A—C14A—N1A	121.33 (11)	H19D—C19B—H19E	109.5
N1A—C15A—C16A	111.90 (10)	N2B—C19B—H19F	109.5
N1A—C15A—H15A	109.2	H19D—C19B—H19F	109.5
C16A—C15A—H15A	109.2	H19E—C19B—H19F	109.5
N1A—C15A—H15B	109.2	O21C—N2C—O22C	123.02 (10)
C16A—C15A—H15B	109.2	O21C—N2C—C2C	118.88 (10)
H15A—C15A—H15B	107.9	O22C—N2C—C2C	118.01 (10)
C17A—C16A—C15A	110.88 (10)	O42C—N4C—O41C	123.09 (11)
C17A—C16A—H16A	109.5	O42C—N4C—C4C	118.58 (11)
C15A—C16A—H16A	109.5	O41C—N4C—C4C	118.33 (11)
C17A—C16A—H16B	109.5	O61C—N6C—O62C	121.82 (11)
C15A—C16A—H16B	109.5	O61C—N6C—C6C	118.33 (11)
H16A—C16A—H16B	108.1	O62C—N6C—C6C	119.83 (10)
N2A—C17A—C16A	113.17 (10)	O1C—C1C—C2C	122.71 (10)
N2A—C17A—H17A	108.9	O1C—C1C—C6C	125.28 (11)
C16A—C17A—H17A	108.9	C2C—C1C—C6C	111.96 (10)
N2A—C17A—H17B	108.9	C3C—C2C—C1C	124.71 (11)
C16A—C17A—H17B	108.9	C3C—C2C—N2C	116.39 (10)
H17A—C17A—H17B	107.8	C1C—C2C—N2C	118.89 (10)
N2A—C18A—H18A	109.5	C2C—C3C—C4C	118.73 (11)
N2A—C18A—H18B	109.5	C2C—C3C—H3CA	120.6
H18A—C18A—H18B	109.5	C4C—C3C—H3CA	120.6
N2A—C18A—H18C	109.5	C5C—C4C—C3C	121.31 (11)
H18A—C18A—H18C	109.5	C5C—C4C—N4C	119.49 (11)
H18B—C18A—H18C	109.5	C3C—C4C—N4C	119.14 (11)
N2A—C19A—H19A	109.5	C6C—C5C—C4C	119.64 (11)
N2A—C19A—H19B	109.5	C6C—C5C—H5CA	120.2
H19A—C19A—H19B	109.5	C4C—C5C—H5CA	120.2
N2A—C19A—H19C	109.5	C5C—C6C—N6C	116.65 (10)
H19A—C19A—H19C	109.5	C5C—C6C—C1C	123.51 (11)
H19B—C19A—H19C	109.5	N6C—C6C—C1C	119.84 (10)
C1B—N1B—C14B	113.91 (9)	O22D—N2D—O21D	121.40 (10)
C1B—N1B—C15B	116.48 (9)	O22D—N2D—C2D	118.52 (10)
C14B—N1B—C15B	116.06 (9)	O21D—N2D—C2D	120.08 (10)
C18B—N2B—C19B	110.68 (11)	O42D—N4D—O41D	123.15 (11)
C18B—N2B—C17B	112.88 (10)	O42D—N4D—C4D	118.23 (11)
C19B—N2B—C17B	109.41 (10)	O41D—N4D—C4D	118.62 (11)
C18B—N2B—H2BB	107.9	O62D—N6D—O61D	123.40 (12)
C19B—N2B—H2BB	107.9	O62D—N6D—C6D	118.39 (11)
C17B—N2B—H2BB	107.9	O61D—N6D—C6D	118.16 (11)
C2B—C1B—C6B	119.35 (11)	O1D—C1D—C6D	122.60 (11)
C2B—C1B—N1B	119.55 (10)	O1D—C1D—C2D	126.13 (11)
C6B—C1B—N1B	121.08 (11)	C6D—C1D—C2D	111.22 (10)
C3B—C2B—C1B	120.54 (12)	C3D—C2D—N2D	116.41 (10)
C3B—C2B—H2BA	119.7	C3D—C2D—C1D	123.81 (10)
C1B—C2B—H2BA	119.7	N2D—C2D—C1D	119.79 (10)
C4B—C3B—C2B	121.28 (13)	C2D—C3D—C4D	119.71 (11)
C4B—C3B—Cl2	119.96 (11)	C2D—C3D—H3DA	120.1
C2B—C3B—Cl2	118.74 (11)	C4D—C3D—H3DA	120.1
C5B—C4B—C3B	117.97 (13)	C3D—C4D—C5D	121.16 (11)
C5B—C4B—H4BA	121.0	C3D—C4D—N4D	119.45 (11)
C3B—C4B—H4BA	121.0	C5D—C4D—N4D	119.37 (11)
C4B—C5B—C6B	123.43 (13)	C6D—C5D—C4D	118.51 (11)
C4B—C5B—H5BA	118.3	C6D—C5D—H5DA	120.7
C6B—C5B—H5BA	118.3	C4D—C5D—H5DA	120.7
C5B—C6B—C1B	117.41 (13)	C5D—C6D—C1D	125.15 (11)
C5B—C6B—C7B	116.14 (12)	C5D—C6D—N6D	117.09 (11)
C1B—C6B—C7B	126.43 (12)	C1D—C6D—N6D	117.76 (10)
C14A—N1A—C1A—C2A	−107.63 (13)	C12B—C13B—C14B—N1B	−177.79 (11)
C15A—N1A—C1A—C2A	33.30 (16)	C10B—C9B—C14B—C13B	−1.22 (19)
C14A—N1A—C1A—C6A	72.36 (14)	C8B—C9B—C14B—C13B	−176.97 (12)
C15A—N1A—C1A—C6A	−146.71 (11)	C10B—C9B—C14B—N1B	178.02 (11)
C6A—C1A—C2A—C3A	−1.34 (18)	C8B—C9B—C14B—N1B	2.26 (18)
N1A—C1A—C2A—C3A	178.65 (11)	C1B—N1B—C14B—C13B	102.50 (13)
C1A—C2A—C3A—C4A	−0.64 (19)	C15B—N1B—C14B—C13B	−36.93 (16)
C1A—C2A—C3A—Cl1	−178.58 (9)	C1B—N1B—C14B—C9B	−76.72 (14)
C2A—C3A—C4A—C5A	1.07 (18)	C15B—N1B—C14B—C9B	143.84 (12)
Cl1—C3A—C4A—C5A	179.03 (9)	C1B—N1B—C15B—C16B	165.18 (10)
C3A—C4A—C5A—C6A	0.48 (19)	C14B—N1B—C15B—C16B	−56.43 (14)
C4A—C5A—C6A—C1A	−2.38 (19)	N1B—C15B—C16B—C17B	−53.28 (14)
C4A—C5A—C6A—C7A	177.53 (12)	C18B—N2B—C17B—C16B	−54.25 (14)
C2A—C1A—C6A—C5A	2.80 (18)	C19B—N2B—C17B—C16B	−177.97 (11)
N1A—C1A—C6A—C5A	−177.19 (11)	C15B—C16B—C17B—N2B	−59.81 (14)
C2A—C1A—C6A—C7A	−177.11 (11)	O1C—C1C—C2C—C3C	−172.94 (12)
N1A—C1A—C6A—C7A	2.90 (17)	C6C—C1C—C2C—C3C	4.51 (17)
C5A—C6A—C7A—C8A	108.32 (14)	O1C—C1C—C2C—N2C	8.32 (18)
C1A—C6A—C7A—C8A	−71.77 (15)	C6C—C1C—C2C—N2C	−174.22 (10)
C6A—C7A—C8A—C9A	53.41 (17)	O21C—N2C—C2C—C3C	−146.36 (12)
C7A—C8A—C9A—C10A	−178.17 (13)	O22C—N2C—C2C—C3C	30.17 (17)
C7A—C8A—C9A—C14A	1.9 (2)	O21C—N2C—C2C—C1C	32.47 (17)
C14A—C9A—C10A—C11A	1.1 (2)	O22C—N2C—C2C—C1C	−151.00 (12)
C8A—C9A—C10A—C11A	−178.89 (13)	C1C—C2C—C3C—C4C	−2.84 (19)
C9A—C10A—C11A—C12A	−1.9 (2)	N2C—C2C—C3C—C4C	175.92 (11)
C10A—C11A—C12A—C13A	0.9 (2)	C2C—C3C—C4C—C5C	0.02 (18)
C11A—C12A—C13A—C14A	0.7 (2)	C2C—C3C—C4C—N4C	−177.33 (11)
C12A—C13A—C14A—C9A	−1.53 (19)	O42C—N4C—C4C—C5C	4.18 (18)
C12A—C13A—C14A—N1A	179.06 (11)	O41C—N4C—C4C—C5C	−176.14 (11)
C10A—C9A—C14A—C13A	0.63 (18)	O42C—N4C—C4C—C3C	−178.43 (11)
C8A—C9A—C14A—C13A	−179.43 (13)	O41C—N4C—C4C—C3C	1.26 (17)
C10A—C9A—C14A—N1A	−179.98 (12)	C3C—C4C—C5C—C6C	0.60 (18)
C8A—C9A—C14A—N1A	0.0 (2)	N4C—C4C—C5C—C6C	177.94 (11)
C1A—N1A—C14A—C13A	119.29 (12)	C4C—C5C—C6C—N6C	−178.20 (11)
C15A—N1A—C14A—C13A	−21.67 (16)	C4C—C5C—C6C—C1C	1.51 (19)
C1A—N1A—C14A—C9A	−60.10 (15)	O61C—N6C—C6C—C5C	−10.99 (18)
C15A—N1A—C14A—C9A	158.94 (11)	O62C—N6C—C6C—C5C	167.41 (12)
C1A—N1A—C15A—C16A	59.19 (14)	O61C—N6C—C6C—C1C	169.29 (13)
C14A—N1A—C15A—C16A	−160.59 (10)	O62C—N6C—C6C—C1C	−12.31 (18)
N1A—C15A—C16A—C17A	63.99 (13)	O1C—C1C—C6C—C5C	173.58 (12)
C19A—N2A—C17A—C16A	−178.29 (10)	C2C—C1C—C6C—C5C	−3.79 (17)
C18A—N2A—C17A—C16A	−54.17 (13)	O1C—C1C—C6C—N6C	−6.71 (19)
C15A—C16A—C17A—N2A	−168.79 (10)	C2C—C1C—C6C—N6C	175.92 (10)
C14B—N1B—C1B—C2B	−122.02 (12)	O22D—N2D—C2D—C3D	0.77 (16)
C15B—N1B—C1B—C2B	17.24 (16)	O21D—N2D—C2D—C3D	−179.14 (12)
C14B—N1B—C1B—C6B	56.77 (16)	O22D—N2D—C2D—C1D	−179.04 (11)
C15B—N1B—C1B—C6B	−163.97 (11)	O21D—N2D—C2D—C1D	1.04 (17)
C6B—C1B—C2B—C3B	−1.29 (18)	O1D—C1D—C2D—C3D	171.41 (12)
N1B—C1B—C2B—C3B	177.51 (11)	C6D—C1D—C2D—C3D	−6.16 (16)
C1B—C2B—C3B—C4B	0.2 (2)	O1D—C1D—C2D—N2D	−8.79 (18)
C1B—C2B—C3B—Cl2	−178.11 (9)	C6D—C1D—C2D—N2D	173.63 (10)
C2B—C3B—C4B—C5B	0.6 (2)	N2D—C2D—C3D—C4D	−178.30 (11)
Cl2—C3B—C4B—C5B	178.84 (10)	C1D—C2D—C3D—C4D	1.50 (18)
C3B—C4B—C5B—C6B	−0.2 (2)	C2D—C3D—C4D—C5D	2.70 (18)
C4B—C5B—C6B—C1B	−0.9 (2)	C2D—C3D—C4D—N4D	−178.33 (11)
C4B—C5B—C6B—C7B	177.65 (13)	O42D—N4D—C4D—C3D	174.21 (11)
C2B—C1B—C6B—C5B	1.62 (18)	O41D—N4D—C4D—C3D	−5.20 (17)
N1B—C1B—C6B—C5B	−177.17 (11)	O42D—N4D—C4D—C5D	−6.80 (17)
C2B—C1B—C6B—C7B	−176.77 (13)	O41D—N4D—C4D—C5D	173.79 (12)
N1B—C1B—C6B—C7B	4.4 (2)	C3D—C4D—C5D—C6D	−1.40 (19)
C5B—C6B—C7B—C8B	179.37 (13)	N4D—C4D—C5D—C6D	179.63 (11)
C1B—C6B—C7B—C8B	−2.2 (2)	C4D—C5D—C6D—C1D	−4.27 (19)
C6B—C7B—C8B—C9B	−56.27 (17)	C4D—C5D—C6D—N6D	176.05 (11)
C7B—C8B—C9B—C10B	−105.22 (15)	O1D—C1D—C6D—C5D	−170.03 (12)
C7B—C8B—C9B—C14B	70.35 (16)	C2D—C1D—C6D—C5D	7.64 (17)
C14B—C9B—C10B—C11B	0.6 (2)	O1D—C1D—C6D—N6D	9.64 (18)
C8B—C9B—C10B—C11B	176.18 (14)	C2D—C1D—C6D—N6D	−172.68 (10)
C9B—C10B—C11B—C12B	−0.2 (2)	O62D—N6D—C6D—C5D	−146.57 (13)
C10B—C11B—C12B—C13B	0.4 (2)	O61D—N6D—C6D—C5D	31.08 (19)
C11B—C12B—C13B—C14B	−0.99 (19)	O62D—N6D—C6D—C1D	33.73 (18)
C12B—C13B—C14B—C9B	1.41 (19)	O61D—N6D—C6D—C1D	−148.62 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2AB···O1D	0.93	1.85	2.7000 (13)	151
N2A—H2AB···O21D	0.93	2.23	2.8982 (14)	128
N2B—H2BB···O1C	0.93	1.92	2.6970 (13)	140
N2B—H2BB···O62C	0.93	2.36	3.0657 (15)	133
C12A—H12A···Cg7i	0.95	2.83	3.656 (4)	145

Cg···Cg	D···A
Cg1···Cg14i	3.838 (8)
Cg7···Cg13ii	3.473 (5)
Cg13···Cg14i	3.590 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2AB⋯O1D	0.93	1.85	2.7000 (13)	151
N2A—H2AB⋯O21D	0.93	2.23	2.8982 (14)	128
N2B—H2BB⋯O1C	0.93	1.92	2.6970 (13)	140
N2B—H2BB⋯O62C	0.93	2.36	3.0657 (15)	133
C12A—H12A⋯Cg7i	0.95	2.83	3.656 (4)	145

Symmetry code: (i) . Cg7 is the centroid of the C1B–C6B ring.

Table 2

π-π hydrogen-bond geometry (Å)

Cg⋯Cg	D⋯A
Cg1⋯Cg14i	3.838 (8)
Cg7⋯Cg13ii	3.473 (5)
Cg13⋯Cg14i	3.590 (5)

Symmetry codes: (i) x, y, z; (ii) 1 − x, y, z; Cg1, Cg7, Cg13 and Cg14 are the centroids of the C1A–C6A, C1B–C6B, C1C–C6C and C1D–C6D rings.