Orphenadrinium picrate.

In the title molecular salt {systematic name: N,N-dimethyl-2-[(2-methyl-phen-yl)(phen-yl)meth-oxy]ethanaminium 2,4,6-tri-nitro-phenolate}, C(18)H(24)NO(+)·C(6)H(2)N(3)O(7) (-), the phenyl rings of the orphenadrinum cation are disordered [occupancies = 0.662 (4) and 0.338 (4)]. The N atom in the orphenadrinum cation is protonated. The picrate anion inter-acts with the protonated N atom through a bifurcated N-H⋯O hydrogen bond, forming an R(1) (2)(6) ring motif with an adjacent cation. The mean planes of the two o-NO(2) and single p-NO(2) groups in the picrate anion are twisted by 23.0 (6), 31.3 (3) and 6.3 (2)° with respect to the mean planes of the six-membered ring. Weak inter-molecular C-H⋯O hydrogen bonds, C-H⋯π inter-molecular inter-actions and weak π-π stacking inter-actions [centroid-centroid distances = 3.677 (2) and 3.515 (3) Å} stabilize the crystal packing, creating a three-dimensional network.

Related literature

For the pharmacological activity of the title compound, see: Hunskaar & Donnel (1991 ▶). For related structures, see: Fun et al. (2010 ▶); Glaser et al. (1992 ▶).

Experimental

Crystal data

C18H24NO+·C6H2N3O7 −

M = 498.49

Triclinic,

a = 9.9434 (10) Å

b = 11.2216 (8) Å

c = 11.3523 (12) Å

α = 78.658 (7)°

β = 76.342 (9)°

γ = 87.660 (7)°

V = 1206.82 (19) Å3

Z = 2

Cu Kα radiation

μ = 0.88 mm−1

T = 123 K

0.52 × 0.43 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.635, T max = 1.000

7402 measured reflections

4677 independent reflections

3760 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.188

S = 1.09

4677 reflections

407 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810049937/bt5424sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049937/bt5424Isup2.hkl

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

C18H24NO+·C6H2N3O7−	Z = 2
Mr = 498.49	F(000) = 524
Triclinic, P1	Dx = 1.372 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.9434 (10) Å	Cell parameters from 3744 reflections
b = 11.2216 (8) Å	θ = 4.6–74.4°
c = 11.3523 (12) Å	µ = 0.88 mm−1
α = 78.658 (7)°	T = 123 K
β = 76.342 (9)°	Triangular plate, yellow
γ = 87.660 (7)°	0.52 × 0.43 × 0.16 mm
V = 1206.82 (19) Å3

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4677 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3760 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 10.5081 pixels mm-1	θmax = 74.6°, θmin = 4.6°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −13→13
Tmin = 0.635, Tmax = 1.000	l = −8→14
7402 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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.188	w = 1/[σ2(Fo2) + (0.093P)2 + 0.5659P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
4677 reflections	Δρmax = 0.45 e Å−3
407 parameters	Δρmin = −0.40 e Å−3
0 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: 0.0038 (11)

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)
O1A	0.7336 (3)	0.61869 (16)	0.6143 (2)	0.0829 (7)
N1A	0.7148 (2)	0.35671 (16)	0.72631 (17)	0.0460 (5)
H1AB	0.7569	0.4148	0.7541	0.055*
C1A	0.6397 (4)	0.7080 (3)	0.6259 (3)	0.0453 (9)	0.662 (4)
H1AA	0.5486	0.6683	0.6695	0.054*	0.662 (4)
C2A	0.6208 (5)	0.7849 (4)	0.5018 (4)	0.051 (2)	0.662 (4)
C3A	0.7346 (4)	0.8060 (4)	0.4020 (6)	0.0592 (16)	0.662 (4)
H3AA	0.8210	0.7696	0.4090	0.071*	0.662 (4)
C4A	0.7220 (4)	0.8805 (3)	0.2918 (4)	0.0681 (13)	0.662 (4)
H4AA	0.7998	0.8949	0.2236	0.082*	0.662 (4)
C5A	0.5956 (6)	0.9339 (3)	0.2815 (3)	0.0590 (14)	0.662 (4)
H5AA	0.5870	0.9848	0.2062	0.071*	0.662 (4)
C6A	0.4818 (4)	0.9128 (4)	0.3813 (5)	0.0531 (17)	0.662 (4)
H6AA	0.3954	0.9493	0.3743	0.064*	0.662 (4)
C7A	0.4944 (4)	0.8383 (3)	0.4915 (4)	0.0464 (11)	0.662 (4)
C8A	0.3672 (4)	0.8167 (3)	0.5954 (4)	0.0581 (11)	0.662 (4)
H8AA	0.2909	0.8607	0.5698	0.087*	0.662 (4)
H8AB	0.3454	0.7315	0.6177	0.087*	0.662 (4)
H8AC	0.3842	0.8445	0.6654	0.087*	0.662 (4)
C9A	0.6762 (5)	0.7860 (3)	0.7096 (4)	0.0536 (11)	0.662 (4)
C10A	0.5891 (5)	0.7873 (3)	0.8248 (4)	0.0708 (15)	0.662 (4)
H10A	0.5069	0.7396	0.8512	0.085*	0.662 (4)
C11A	0.6224 (6)	0.8585 (4)	0.9013 (3)	0.087 (2)	0.662 (4)
H11A	0.5629	0.8594	0.9801	0.104*	0.662 (4)
C12A	0.7428 (6)	0.9283 (4)	0.8627 (4)	0.075 (3)	0.662 (4)
H12A	0.7656	0.9769	0.9150	0.091*	0.662 (4)
C13A	0.8299 (5)	0.9269 (4)	0.7475 (5)	0.081 (2)	0.662 (4)
H13A	0.9121	0.9747	0.7210	0.097*	0.662 (4)
C14A	0.7966 (4)	0.8558 (4)	0.6709 (4)	0.0721 (18)	0.662 (4)
H14A	0.8561	0.8549	0.5922	0.087*	0.662 (4)
C15A	0.7104 (3)	0.5276 (2)	0.5497 (2)	0.0519 (6)
H15A	0.8002	0.4997	0.5049	0.062*
H15B	0.6562	0.5621	0.4884	0.062*
C16A	0.6334 (3)	0.4220 (2)	0.6388 (2)	0.0473 (5)
H16A	0.5464	0.4517	0.6867	0.057*
H16B	0.6085	0.3642	0.5917	0.057*
C17A	0.6223 (3)	0.2806 (2)	0.8360 (2)	0.0589 (7)
H17A	0.5585	0.3332	0.8822	0.088*
H17B	0.6785	0.2345	0.8895	0.088*
H17C	0.5694	0.2241	0.8084	0.088*
C18A	0.8262 (3)	0.2799 (2)	0.6658 (2)	0.0598 (7)
H18A	0.8846	0.3300	0.5925	0.090*
H18B	0.7841	0.2140	0.6414	0.090*
H18C	0.8828	0.2454	0.7240	0.090*
C1C	0.7475 (7)	0.7270 (6)	0.5766 (6)	0.0435 (16)	0.338 (4)
H1CA	0.8407	0.7363	0.5182	0.052*	0.338 (4)
C2C	0.7572 (7)	0.8018 (5)	0.6752 (4)	0.0309 (14)	0.338 (4)
C3C	0.6651 (6)	0.7736 (5)	0.7898 (6)	0.0416 (17)	0.338 (4)
H3CA	0.5985	0.7106	0.8053	0.050*	0.338 (4)
C4C	0.6704 (8)	0.8374 (8)	0.8819 (5)	0.053 (2)	0.338 (4)
H4CA	0.6074	0.8181	0.9603	0.064*	0.338 (4)
C5C	0.7678 (11)	0.9295 (8)	0.8593 (7)	0.075 (5)	0.338 (4)
H5CA	0.7714	0.9731	0.9223	0.090*	0.338 (4)
C6C	0.8599 (9)	0.9577 (7)	0.7447 (8)	0.057 (3)	0.338 (4)
H6CA	0.9265	1.0207	0.7293	0.068*	0.338 (4)
C7C	0.8547 (6)	0.8939 (6)	0.6526 (5)	0.0482 (19)	0.338 (4)
C8C	0.9529 (9)	0.9303 (7)	0.5317 (9)	0.067 (2)	0.338 (4)
H8CA	1.0122	0.9947	0.5342	0.101*	0.338 (4)
H8CB	1.0081	0.8620	0.5104	0.101*	0.338 (4)
H8CC	0.9002	0.9581	0.4708	0.101*	0.338 (4)
C9C	0.6485 (10)	0.7893 (8)	0.4994 (8)	0.045 (3)	0.338 (4)
C10C	0.7073 (8)	0.8359 (8)	0.3758 (8)	0.057 (3)	0.338 (4)
H10B	0.8034	0.8260	0.3434	0.069*	0.338 (4)
C11C	0.6255 (12)	0.8969 (7)	0.2996 (7)	0.081 (5)	0.338 (4)
H11B	0.6656	0.9287	0.2152	0.097*	0.338 (4)
C12C	0.4848 (11)	0.9113 (8)	0.3471 (10)	0.064 (4)	0.338 (4)
H12B	0.4289	0.9530	0.2950	0.077*	0.338 (4)
C13C	0.4260 (8)	0.8648 (8)	0.4707 (10)	0.074 (3)	0.338 (4)
H13B	0.3299	0.8746	0.5031	0.089*	0.338 (4)
C14C	0.5079 (11)	0.8038 (7)	0.5468 (7)	0.069 (3)	0.338 (4)
H14B	0.4677	0.7720	0.6313	0.083*	0.338 (4)
O1B	0.78560 (18)	0.46162 (16)	0.89387 (15)	0.0545 (4)
O2B	0.6057 (2)	0.4845 (2)	1.10418 (19)	0.0708 (6)
O3B	0.71427 (19)	0.50961 (19)	1.23996 (16)	0.0624 (5)
O4B	1.0321 (2)	0.85253 (18)	1.1050 (2)	0.0723 (6)
O5B	1.1774 (2)	0.8672 (2)	0.9274 (2)	0.0818 (7)
O6B	1.0764 (2)	0.6666 (2)	0.62610 (18)	0.0766 (6)
O7B	0.98789 (19)	0.4863 (2)	0.68726 (18)	0.0680 (6)
N1B	0.70630 (19)	0.52022 (17)	1.13249 (17)	0.0461 (5)
N2B	1.0733 (3)	0.8227 (2)	1.0032 (2)	0.0606 (6)
N3B	1.0114 (2)	0.5869 (2)	0.70603 (19)	0.0574 (6)
C1B	0.8494 (2)	0.5445 (2)	0.9157 (2)	0.0429 (5)
C2B	0.8186 (2)	0.58148 (19)	1.03509 (19)	0.0406 (5)
C3B	0.8897 (2)	0.6690 (2)	1.0645 (2)	0.0434 (5)
H3BA	0.8658	0.6876	1.1449	0.052*
C4B	0.9972 (2)	0.7300 (2)	0.9748 (2)	0.0474 (5)
C5B	1.0340 (2)	0.7033 (2)	0.8576 (2)	0.0491 (6)
H5BA	1.1069	0.7469	0.7967	0.059*
C6B	0.9642 (2)	0.6133 (2)	0.8304 (2)	0.0466 (5)

	U11	U22	U33	U12	U13	U23
O1A	0.140 (2)	0.0331 (9)	0.1071 (17)	0.0224 (10)	−0.0862 (16)	−0.0234 (10)
N1A	0.0622 (12)	0.0382 (9)	0.0454 (10)	0.0079 (8)	−0.0212 (9)	−0.0178 (8)
C1A	0.057 (2)	0.0313 (15)	0.0513 (19)	−0.0021 (14)	−0.0189 (17)	−0.0076 (14)
C2A	0.062 (4)	0.031 (3)	0.071 (5)	0.005 (2)	−0.030 (3)	−0.016 (3)
C3A	0.058 (3)	0.041 (3)	0.079 (4)	0.008 (2)	−0.026 (3)	−0.004 (3)
C4A	0.080 (3)	0.049 (3)	0.070 (3)	−0.006 (2)	−0.008 (3)	−0.008 (2)
C5A	0.091 (4)	0.035 (3)	0.054 (3)	−0.005 (2)	−0.029 (3)	−0.0009 (19)
C6A	0.073 (4)	0.032 (3)	0.072 (4)	0.004 (2)	−0.044 (3)	−0.020 (3)
C7A	0.055 (3)	0.036 (2)	0.056 (3)	−0.0089 (19)	−0.018 (2)	−0.019 (2)
C8A	0.057 (2)	0.046 (2)	0.077 (3)	0.0000 (16)	−0.018 (2)	−0.0214 (19)
C9A	0.082 (4)	0.0247 (16)	0.065 (3)	−0.0023 (19)	−0.044 (3)	−0.0008 (18)
C10A	0.111 (5)	0.043 (2)	0.064 (3)	−0.020 (3)	−0.033 (3)	−0.005 (2)
C11A	0.160 (7)	0.047 (3)	0.064 (3)	−0.026 (4)	−0.050 (4)	−0.003 (2)
C12A	0.140 (6)	0.035 (4)	0.073 (5)	0.000 (4)	−0.073 (4)	−0.003 (3)
C13A	0.093 (4)	0.031 (3)	0.145 (7)	0.011 (3)	−0.079 (4)	−0.021 (3)
C14A	0.074 (4)	0.041 (3)	0.121 (5)	0.001 (2)	−0.054 (4)	−0.025 (3)
C15A	0.0719 (16)	0.0363 (11)	0.0548 (13)	0.0091 (10)	−0.0261 (12)	−0.0140 (10)
C16A	0.0583 (13)	0.0382 (11)	0.0546 (13)	0.0084 (9)	−0.0244 (11)	−0.0189 (10)
C17A	0.0827 (18)	0.0481 (13)	0.0508 (14)	−0.0061 (12)	−0.0209 (13)	−0.0134 (11)
C18A	0.0833 (18)	0.0522 (14)	0.0529 (14)	0.0280 (13)	−0.0283 (13)	−0.0222 (11)
C1C	0.048 (4)	0.041 (3)	0.041 (3)	0.000 (3)	−0.010 (3)	−0.008 (3)
C2C	0.030 (3)	0.027 (4)	0.036 (3)	−0.005 (3)	−0.011 (3)	−0.001 (3)
C3C	0.049 (4)	0.040 (4)	0.037 (4)	0.006 (3)	−0.019 (4)	0.001 (3)
C4C	0.067 (5)	0.049 (5)	0.048 (4)	0.021 (4)	−0.021 (4)	−0.017 (4)
C5C	0.076 (7)	0.036 (8)	0.133 (16)	0.004 (5)	−0.057 (9)	−0.029 (9)
C6C	0.097 (7)	0.021 (4)	0.067 (6)	0.004 (4)	−0.045 (5)	−0.014 (3)
C7C	0.058 (5)	0.029 (4)	0.063 (5)	−0.001 (3)	−0.027 (4)	−0.007 (3)
C8C	0.066 (5)	0.050 (4)	0.080 (6)	−0.009 (4)	−0.006 (4)	−0.010 (4)
C9C	0.070 (7)	0.029 (5)	0.047 (7)	0.001 (4)	−0.032 (6)	−0.012 (4)
C10C	0.072 (6)	0.043 (6)	0.066 (7)	0.005 (4)	−0.045 (6)	0.001 (5)
C11C	0.138 (14)	0.036 (6)	0.092 (9)	−0.004 (7)	−0.079 (10)	−0.001 (5)
C12C	0.102 (11)	0.029 (5)	0.083 (8)	0.002 (5)	−0.056 (8)	−0.019 (5)
C13C	0.096 (8)	0.050 (5)	0.100 (10)	−0.004 (6)	−0.047 (8)	−0.038 (6)
C14C	0.110 (10)	0.048 (6)	0.075 (7)	0.018 (5)	−0.054 (7)	−0.039 (5)
O1B	0.0585 (10)	0.0651 (11)	0.0472 (9)	−0.0057 (8)	−0.0170 (7)	−0.0212 (8)
O2B	0.0593 (11)	0.0916 (15)	0.0678 (12)	−0.0224 (10)	−0.0065 (9)	−0.0355 (11)
O3B	0.0582 (10)	0.0834 (13)	0.0450 (9)	−0.0066 (9)	−0.0144 (8)	−0.0062 (9)
O4B	0.0985 (15)	0.0594 (11)	0.0697 (13)	−0.0230 (10)	−0.0421 (11)	−0.0059 (10)
O5B	0.0861 (15)	0.0765 (14)	0.0795 (14)	−0.0389 (12)	−0.0260 (12)	0.0090 (11)
O6B	0.0816 (14)	0.0921 (16)	0.0471 (11)	0.0039 (12)	−0.0065 (10)	−0.0027 (10)
O7B	0.0557 (11)	0.0980 (16)	0.0585 (11)	0.0003 (10)	−0.0114 (8)	−0.0363 (11)
N1B	0.0460 (10)	0.0497 (11)	0.0460 (10)	−0.0003 (8)	−0.0126 (8)	−0.0148 (8)
N2B	0.0753 (15)	0.0520 (12)	0.0589 (13)	−0.0151 (11)	−0.0351 (12)	0.0054 (10)
N3B	0.0517 (11)	0.0799 (16)	0.0392 (11)	0.0083 (10)	−0.0123 (9)	−0.0079 (11)
C1B	0.0445 (11)	0.0504 (12)	0.0400 (11)	0.0042 (9)	−0.0205 (9)	−0.0115 (9)
C2B	0.0436 (11)	0.0416 (11)	0.0403 (11)	0.0020 (8)	−0.0177 (9)	−0.0069 (9)
C3B	0.0520 (12)	0.0425 (11)	0.0412 (11)	0.0013 (9)	−0.0236 (10)	−0.0056 (9)
C4B	0.0529 (13)	0.0437 (11)	0.0501 (13)	−0.0050 (9)	−0.0282 (10)	0.0009 (10)
C5B	0.0473 (12)	0.0542 (13)	0.0440 (12)	−0.0009 (10)	−0.0195 (10)	0.0059 (10)
C6B	0.0460 (12)	0.0581 (13)	0.0390 (11)	0.0088 (10)	−0.0190 (9)	−0.0078 (10)

O1A—C1C	1.208 (7)	C1C—C2C	1.548 (8)
O1A—C1A	1.346 (4)	C1C—H1CA	1.0000
O1A—C15A	1.425 (3)	C2C—C3C	1.3900
N1A—C16A	1.491 (3)	C2C—C7C	1.3900
N1A—C17A	1.494 (3)	C3C—C4C	1.3900
N1A—C18A	1.495 (3)	C3C—H3CA	0.9500
N1A—H1AB	0.9300	C4C—C5C	1.3900
C1A—C9A	1.522 (4)	C4C—H4CA	0.9500
C1A—C2A	1.549 (5)	C5C—C6C	1.3900
C1A—H1AA	1.0000	C5C—H5CA	0.9500
C2A—C3A	1.3900	C6C—C7C	1.3900
C2A—C7A	1.3900	C6C—H6CA	0.9500
C3A—C4A	1.3900	C7C—C8C	1.478 (10)
C3A—H3AA	0.9500	C8C—C8Ci	1.789 (15)
C4A—C5A	1.3900	C8C—H8CA	0.9600
C4A—H4AA	0.9500	C8C—H8CB	0.9600
C5A—C6A	1.3900	C8C—H8CC	0.9601
C5A—H5AA	0.9500	C9C—C10C	1.3900
C6A—C7A	1.3900	C9C—C14C	1.3900
C6A—H6AA	0.9500	C10C—C11C	1.3900
C7A—C8A	1.503 (6)	C10C—H10B	0.9500
C8A—H8AA	0.9600	C11C—C12C	1.3900
C8A—H8AB	0.9600	C11C—H11B	0.9500
C8A—H8AC	0.9601	C12C—C13C	1.3900
C9A—C10A	1.3900	C12C—H12B	0.9500
C9A—C14A	1.3900	C13C—C14C	1.3900
C10A—C11A	1.3900	C13C—H8AA	1.5316
C10A—H10A	0.9500	C13C—H13B	0.9500
C11A—C12A	1.3900	C14C—H14B	0.9500
C11A—H11A	0.9500	O1B—C1B	1.242 (3)
C12A—C13A	1.3900	O2B—N1B	1.225 (3)
C12A—H12A	0.9500	O3B—N1B	1.223 (3)
C13A—C14A	1.3900	O4B—N2B	1.238 (3)
C13A—H13A	0.9500	O5B—N2B	1.231 (3)
C14A—H14A	0.9500	O6B—N3B	1.221 (3)
C15A—C16A	1.501 (3)	O7B—N3B	1.230 (3)
C15A—H15A	0.9900	N1B—C2B	1.457 (3)
C15A—H15B	0.9900	N2B—C4B	1.438 (3)
C16A—H16A	0.9900	N3B—C6B	1.463 (3)
C16A—H16B	0.9900	C1B—C6B	1.447 (3)
C17A—H17A	0.9800	C1B—C2B	1.455 (3)
C17A—H17B	0.9800	C2B—C3B	1.369 (3)
C17A—H17C	0.9800	C3B—C4B	1.385 (3)
C18A—H18A	0.9800	C3B—H3BA	0.9500
C18A—H18B	0.9800	C4B—C5B	1.383 (3)
C18A—H18C	0.9800	C5B—C6B	1.371 (3)
C1C—C9C	1.528 (8)	C5B—H5BA	0.9500
C1C—O1A—C1A	50.3 (4)	O1A—C1C—C9C	117.4 (6)
C1C—O1A—C15A	128.2 (4)	O1A—C1C—C2C	114.9 (5)
C1A—O1A—C15A	117.7 (2)	C9C—C1C—C2C	109.5 (6)
C16A—N1A—C17A	110.9 (2)	O1A—C1C—H1CA	104.5
C16A—N1A—C18A	112.23 (17)	C9C—C1C—H1CA	104.5
C17A—N1A—C18A	110.01 (19)	C2C—C1C—H1CA	104.5
C16A—N1A—H1AB	107.9	C3C—C2C—C7C	120.0
C17A—N1A—H1AB	107.9	C3C—C2C—C1C	117.8 (5)
C18A—N1A—H1AB	107.9	C7C—C2C—C1C	122.2 (5)
O1A—C1A—C9A	108.7 (3)	C2C—C3C—C4C	120.0
O1A—C1A—C2A	114.5 (3)	C2C—C3C—H3CA	120.0
C9A—C1A—C2A	112.2 (3)	C4C—C3C—H3CA	120.0
O1A—C1A—H1AA	107.0	C3C—C4C—C5C	120.0
C9A—C1A—H1AA	107.0	C3C—C4C—H4CA	120.0
C2A—C1A—H1AA	107.0	C5C—C4C—H4CA	120.0
C3A—C2A—C7A	120.0	C4C—C5C—C6C	120.0
C3A—C2A—C1A	118.9 (4)	C4C—C5C—H5CA	120.0
C7A—C2A—C1A	121.0 (4)	C6C—C5C—H5CA	120.0
C4A—C3A—C2A	120.0	C5C—C6C—C7C	120.0
C4A—C3A—H3AA	120.0	C5C—C6C—H6CA	120.0
C2A—C3A—H3AA	120.0	C7C—C6C—H6CA	120.0
C3A—C4A—C5A	120.0	C6C—C7C—C2C	120.0
C3A—C4A—H4AA	120.0	C6C—C7C—C8C	117.5 (6)
C5A—C4A—H4AA	120.0	C2C—C7C—C8C	122.5 (6)
C4A—C5A—C6A	120.0	C7C—C8C—C8Ci	129.1 (9)
C4A—C5A—H5AA	120.0	C7C—C8C—H8CA	110.3
C6A—C5A—H5AA	120.0	C7C—C8C—H8CB	110.1
C7A—C6A—C5A	120.0	C8Ci—C8C—H8CB	111.1
C7A—C6A—H6AA	120.0	H8CA—C8C—H8CB	109.5
C5A—C6A—H6AA	120.0	C7C—C8C—H8CC	108.0
C6A—C7A—C2A	120.0	C8Ci—C8C—H8CC	84.9
C6A—C7A—C8A	117.6 (4)	H8CA—C8C—H8CC	109.5
C2A—C7A—C8A	122.3 (4)	H8CB—C8C—H8CC	109.5
C7A—C8A—H8AA	109.6	C10C—C9C—C14C	120.0
C7A—C8A—H8AB	109.7	C10C—C9C—C1C	116.2 (7)
H8AA—C8A—H8AB	109.5	C14C—C9C—C1C	123.8 (7)
C7A—C8A—H8AC	109.2	C11C—C10C—C9C	120.0
H8AA—C8A—H8AC	109.5	C11C—C10C—H10B	120.0
H8AB—C8A—H8AC	109.5	C9C—C10C—H10B	120.0
C10A—C9A—C14A	120.0	C10C—C11C—C12C	120.0
C10A—C9A—C1A	120.0 (3)	C10C—C11C—H11B	120.0
C14A—C9A—C1A	120.0 (3)	C12C—C11C—H11B	120.0
C9A—C10A—C11A	120.0	C11C—C12C—C13C	120.0
C9A—C10A—H10A	120.0	C11C—C12C—H12B	120.0
C11A—C10A—H10A	120.0	C13C—C12C—H12B	120.0
C12A—C11A—C10A	120.0	C14C—C13C—C12C	120.0
C12A—C11A—H11A	120.0	C14C—C13C—H8AA	97.3
C10A—C11A—H11A	120.0	C12C—C13C—H8AA	142.5
C11A—C12A—C13A	120.0	C14C—C13C—H13B	120.0
C11A—C12A—H12A	120.0	C12C—C13C—H13B	120.0
C13A—C12A—H12A	120.0	C13C—C14C—C9C	120.0
C14A—C13A—C12A	120.0	C13C—C14C—H14B	120.0
C14A—C13A—H13A	120.0	C9C—C14C—H14B	120.0
C12A—C13A—H13A	120.0	O3B—N1B—O2B	122.4 (2)
C13A—C14A—C9A	120.0	O3B—N1B—C2B	118.62 (18)
C13A—C14A—H14A	120.0	O2B—N1B—C2B	118.94 (19)
C9A—C14A—H14A	120.0	O5B—N2B—O4B	122.7 (2)
O1A—C15A—C16A	110.1 (2)	O5B—N2B—C4B	119.3 (2)
O1A—C15A—H15A	109.6	O4B—N2B—C4B	118.0 (2)
C16A—C15A—H15A	109.6	O6B—N3B—O7B	123.2 (2)
O1A—C15A—H15B	109.6	O6B—N3B—C6B	117.2 (2)
C16A—C15A—H15B	109.6	O7B—N3B—C6B	119.5 (2)
H15A—C15A—H15B	108.2	O1B—C1B—C6B	125.6 (2)
N1A—C16A—C15A	113.0 (2)	O1B—C1B—C2B	122.9 (2)
N1A—C16A—H16A	109.0	C6B—C1B—C2B	111.48 (19)
C15A—C16A—H16A	109.0	C3B—C2B—C1B	124.7 (2)
N1A—C16A—H16B	109.0	C3B—C2B—N1B	116.68 (19)
C15A—C16A—H16B	109.0	C1B—C2B—N1B	118.60 (18)
H16A—C16A—H16B	107.8	C2B—C3B—C4B	118.8 (2)
N1A—C17A—H17A	109.5	C2B—C3B—H3BA	120.6
N1A—C17A—H17B	109.5	C4B—C3B—H3BA	120.6
H17A—C17A—H17B	109.5	C5B—C4B—C3B	121.3 (2)
N1A—C17A—H17C	109.5	C5B—C4B—N2B	118.8 (2)
H17A—C17A—H17C	109.5	C3B—C4B—N2B	119.9 (2)
H17B—C17A—H17C	109.5	C6B—C5B—C4B	119.3 (2)
N1A—C18A—H18A	109.5	C6B—C5B—H5BA	120.4
N1A—C18A—H18B	109.5	C4B—C5B—H5BA	120.4
H18A—C18A—H18B	109.5	C5B—C6B—C1B	124.4 (2)
N1A—C18A—H18C	109.5	C5B—C6B—N3B	116.5 (2)
H18A—C18A—H18C	109.5	C1B—C6B—N3B	119.1 (2)
H18B—C18A—H18C	109.5
C1C—O1A—C1A—C9A	−68.1 (5)	C5C—C6C—C7C—C2C	0.0
C15A—O1A—C1A—C9A	173.7 (3)	C5C—C6C—C7C—C8C	178.4 (6)
C1C—O1A—C1A—C2A	58.2 (5)	C3C—C2C—C7C—C6C	0.0
C15A—O1A—C1A—C2A	−60.0 (4)	C1C—C2C—C7C—C6C	−179.4 (6)
O1A—C1A—C2A—C3A	−33.7 (4)	C3C—C2C—C7C—C8C	−178.4 (6)
C9A—C1A—C2A—C3A	90.8 (4)	C1C—C2C—C7C—C8C	2.2 (8)
O1A—C1A—C2A—C7A	150.0 (3)	C6C—C7C—C8C—C8Ci	−19.3 (14)
C9A—C1A—C2A—C7A	−85.5 (4)	C2C—C7C—C8C—C8Ci	159.1 (10)
C7A—C2A—C3A—C4A	0.0	O1A—C1C—C9C—C10C	−113.0 (6)
C1A—C2A—C3A—C4A	−176.3 (4)	C2C—C1C—C9C—C10C	113.7 (6)
C2A—C3A—C4A—C5A	0.0	O1A—C1C—C9C—C14C	68.7 (9)
C3A—C4A—C5A—C6A	0.0	C2C—C1C—C9C—C14C	−64.6 (8)
C4A—C5A—C6A—C7A	0.0	C14C—C9C—C10C—C11C	0.0
C5A—C6A—C7A—C2A	0.0	C1C—C9C—C10C—C11C	−178.3 (8)
C5A—C6A—C7A—C8A	−178.8 (3)	C9C—C10C—C11C—C12C	0.0
C3A—C2A—C7A—C6A	0.0	C10C—C11C—C12C—C13C	0.0
C1A—C2A—C7A—C6A	176.2 (4)	C11C—C12C—C13C—C14C	0.0
C3A—C2A—C7A—C8A	178.7 (3)	C12C—C13C—C14C—C9C	0.0
C1A—C2A—C7A—C8A	−5.0 (4)	C10C—C9C—C14C—C13C	0.0
O1A—C1A—C9A—C10A	−113.1 (3)	C1C—C9C—C14C—C13C	178.2 (9)
C2A—C1A—C9A—C10A	119.2 (4)	O1B—C1B—C2B—C3B	177.3 (2)
O1A—C1A—C9A—C14A	66.9 (4)	C6B—C1B—C2B—C3B	−0.8 (3)
C2A—C1A—C9A—C14A	−60.8 (4)	O1B—C1B—C2B—N1B	−1.3 (3)
C14A—C9A—C10A—C11A	0.0	C6B—C1B—C2B—N1B	−179.36 (19)
C1A—C9A—C10A—C11A	180.0 (3)	O3B—N1B—C2B—C3B	−29.4 (3)
C9A—C10A—C11A—C12A	0.0	O2B—N1B—C2B—C3B	148.4 (2)
C10A—C11A—C12A—C13A	0.0	O3B—N1B—C2B—C1B	149.3 (2)
C11A—C12A—C13A—C14A	0.0	O2B—N1B—C2B—C1B	−32.9 (3)
C12A—C13A—C14A—C9A	0.0	C1B—C2B—C3B—C4B	1.5 (3)
C10A—C9A—C14A—C13A	0.0	N1B—C2B—C3B—C4B	−179.84 (19)
C1A—C9A—C14A—C13A	−180.0 (3)	C2B—C3B—C4B—C5B	−0.6 (3)
C1C—O1A—C15A—C16A	−152.5 (5)	C2B—C3B—C4B—N2B	179.8 (2)
C1A—O1A—C15A—C16A	−92.8 (3)	O5B—N2B—C4B—C5B	−7.2 (4)
C17A—N1A—C16A—C15A	161.73 (19)	O4B—N2B—C4B—C5B	174.2 (2)
C18A—N1A—C16A—C15A	−74.8 (2)	O5B—N2B—C4B—C3B	172.5 (2)
O1A—C15A—C16A—N1A	−65.3 (3)	O4B—N2B—C4B—C3B	−6.2 (3)
C1A—O1A—C1C—C9C	−53.1 (6)	C3B—C4B—C5B—C6B	−1.1 (3)
C15A—O1A—C1C—C9C	43.5 (9)	N2B—C4B—C5B—C6B	178.5 (2)
C1A—O1A—C1C—C2C	77.7 (6)	C4B—C5B—C6B—C1B	1.9 (4)
C15A—O1A—C1C—C2C	174.4 (4)	C4B—C5B—C6B—N3B	−178.1 (2)
O1A—C1C—C2C—C3C	−43.8 (7)	O1B—C1B—C6B—C5B	−179.0 (2)
C9C—C1C—C2C—C3C	90.7 (6)	C2B—C1B—C6B—C5B	−1.0 (3)
O1A—C1C—C2C—C7C	135.6 (5)	O1B—C1B—C6B—N3B	0.9 (3)
C9C—C1C—C2C—C7C	−89.8 (7)	C2B—C1B—C6B—N3B	178.98 (19)
C7C—C2C—C3C—C4C	0.0	O6B—N3B—C6B—C5B	−21.7 (3)
C1C—C2C—C3C—C4C	179.5 (6)	O7B—N3B—C6B—C5B	156.2 (2)
C2C—C3C—C4C—C5C	0.0	O6B—N3B—C6B—C1B	158.3 (2)
C3C—C4C—C5C—C6C	0.0	O7B—N3B—C6B—C1B	−23.8 (3)
C4C—C5C—C6C—C7C	0.0

Cg2 and Cg3 are the centroids of the C9A–C7A and C2C–C7C rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AB···O1B	0.93	1.85	2.661 (2)	144.
N1A—H1AB···O7B	0.93	2.36	3.031 (3)	129.
C4A—H4AA···O4Bii	0.95	2.46	3.346 (4)	155.
C16A—H16A···O3Biii	0.99	2.57	3.519 (3)	160.
C17A—H17A···O2Biii	0.98	2.57	3.470 (4)	153.
C18A—H18A···O6Biv	0.98	2.41	3.167 (3)	133.
C18A—H18C···O4Bv	0.98	2.36	3.317 (3)	166.
C8C—H8CB···O6B	0.96	2.48	3.239 (9)	136.
C6A—H6AA···Cg2vi	0.93	2.88	3.643 (2)	138.
C6A—H6AA···Cg3vi	0.93	3.00	3.836 (4)	148.
C12C—H12B···Cg2vi	0.93	2.62	3.492 (4)	153.
C12C—H12B···Cg3vi	0.93	2.83	3.704 (4)	153.

	CgI···CgJ (Å)	CgI···Perp (Å)	CgJ···Perp (Å)
Cg2···Cg5i	3.677 (2)	-3.616 (2)	-3.6243 (9)
Cg3···Cg5i	3.515 (3)	-3.374 (3)	3.3844 (9)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C9A–C7A and C2C–C7C rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1AB⋯O1B	0.93	1.85	2.661 (2)	144
N1A—H1AB⋯O7B	0.93	2.36	3.031 (3)	129
C4A—H4AA⋯O4Bi	0.95	2.46	3.346 (4)	155
C16A—H16A⋯O3Bii	0.99	2.57	3.519 (3)	160
C17A—H17A⋯O2Bii	0.98	2.57	3.470 (4)	153
C18A—H18A⋯O6Biii	0.98	2.41	3.167 (3)	133
C18A—H18C⋯O4Biv	0.98	2.36	3.317 (3)	166
C8C—H8CB⋯O6B	0.96	2.48	3.239 (9)	136
C6A—H6AA⋯Cg2v	0.93	2.88	3.643 (2)	138
C6A—H6AA⋯Cg3v	0.93	3.00	3.836 (4)	148
C12C—H12B⋯Cg2v	0.93	2.62	3.492 (4)	153
C12C—H12B⋯Cg3v	0.93	2.83	3.704 (4)	153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .