Propiverinium picrate.

THE TITLE COMPOUND [SYSTEMATIC NAME: 4-(2,2-diphenyl-2-prop-oxyacet-oxy)-1-methyl-piperidin-1-ium picrate], C(23)H(30)NO(3) (+)·C(6)H(2)N(3)O(7) (-), crystallizes as a salt with one cation-anion (propiverinium picrate) pair in the asymmetric unit. A significant number of conformational changes are observed between the crystalline environment of this cation-anion salt and that of a density functional theory (DFT) calculation of the geometry-optimized structure. The angle between the dihedral planes of the two benzyl rings in the propiverinium cation increases by 14.4 (0)° from that of the crystalline environment. The dihedral angles between the mean planes of each of the benzyl rings and the mean plane of the piperidine increase by 2.0 (8) and 12.3 (5)°. The angles between the mean plane of the acetate group and the mean planes of the inter-connected piperidine group and the two benzyl rings decrease by 0.2 (1), 7.4 (6) and 3.2 (2)°, respectively. The mean plane of the phenolate group in the anion changes by +22.6 (9), +22.1 (1) and -2.8 (6)° from the mean planes of the piperidine and benzyl rings in the cation, respectively. In the crystal, a bifurcated N-H⋯(O,O) hydrogen bond and a weak C-H⋯π ring inter-action help to establish the packing. The two O atoms of the p-NO(2) group are disordered with occupancies 0.825 (10):0.175 (10).

Related literature

For related structures, see: Bindya et al. (2007 ▶); Harrison, Bindya et al. (2007 ▶); Harrison, Sreevidya et al. (2007 ▶); Swamy et al. (2007 ▶) Yathirajan et al. (2007 ▶). For background, see: Chapple et al. (2008 ▶); Jünemann et al. (2006 ▶); Madersbacher & Gramatté, (2006 ▶); Matsushima et al. (1997 ▶); Noguchi & Masuda, (1998 ▶); Okada & Sengodu, (1998 ▶); Rong et al. (1999 ▶). For density functional theory (DFT), see: Becke (1988 ▶, 1993 ▶); Frisch et al. (2004 ▶); Hehre et al. (1986 ▶); Lee et al. (1988 ▶); Schmidt & Polik (2007 ▶); Szumma et al. (2000 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C23H30NO3 +·C6H2N3O7 −

M = 596.59

Triclinic,

a = 8.9379 (4) Å

b = 9.2885 (4) Å

c = 18.0750 (7) Å

α = 97.652 (3)°

β = 97.630 (3)°

γ = 104.301 (4)°

V = 1419.54 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 110 K

0.55 × 0.35 × 0.27 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.910, T max = 0.972

18429 measured reflections

9328 independent reflections

6353 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.126

S = 1.03

9328 reflections

397 parameters

24 restraints

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlisPro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlisPro (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/S1600536809022995/at2814sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022995/at2814Isup2.hkl

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

C23H30NO3+·C6H2N3O7−	Z = 2
Mr = 596.59	F(000) = 628
Triclinic, P1	Dx = 1.396 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9379 (4) Å	Cell parameters from 8020 reflections
b = 9.2885 (4) Å	θ = 4.7–32.6°
c = 18.0750 (7) Å	µ = 0.11 mm−1
α = 97.652 (3)°	T = 110 K
β = 97.630 (3)°	Prism, pale yellow
γ = 104.301 (4)°	0.55 × 0.35 × 0.27 mm
V = 1419.54 (10) Å3

Oxford Diffraction Gemini R CCD diffractometer	9328 independent reflections
Radiation source: fine-focus sealed tube	6353 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 10.5081 pixels mm-1	θmax = 32.7°, θmin = 4.8°
φ and ω scans	h = −10→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −12→14
Tmin = 0.910, Tmax = 0.972	l = −25→26
18429 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0682P)2] where P = (Fo2 + 2Fc2)/3
9328 reflections	(Δ/σ)max = 0.001
397 parameters	Δρmax = 0.39 e Å−3
24 restraints	Δρmin = −0.31 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	Occ. (<1)
O1A	0.10752 (10)	0.23733 (10)	0.53343 (5)	0.02465 (19)
O2A	0.12422 (13)	0.08237 (12)	0.64704 (6)	0.0414 (3)
O3A	0.14903 (16)	−0.14166 (12)	0.61794 (7)	0.0549 (3)
O4AA	0.4251 (3)	−0.2570 (3)	0.4160 (2)	0.0556 (8)	0.825 (10)
O5AA	0.4834 (4)	−0.0983 (5)	0.33859 (12)	0.0463 (8)	0.825 (10)
O4AB	0.4136 (17)	−0.2763 (15)	0.4447 (10)	0.0556 (8)	0.175 (10)
O5AB	0.4388 (16)	−0.1576 (18)	0.3475 (7)	0.0463 (8)	0.175 (10)
O6A	0.19712 (11)	0.28535 (11)	0.33215 (5)	0.0302 (2)
O7A	0.24781 (13)	0.42205 (10)	0.44357 (5)	0.0365 (2)
N1A	0.15738 (14)	−0.01478 (13)	0.60401 (7)	0.0341 (3)
N2A	0.41627 (16)	−0.14450 (15)	0.39320 (9)	0.0470 (4)
N3A	0.22611 (12)	0.30132 (12)	0.40164 (6)	0.0234 (2)
C1A	0.18060 (13)	0.15168 (13)	0.50522 (6)	0.0197 (2)
C2A	0.20815 (15)	0.02039 (13)	0.53354 (7)	0.0251 (3)
C3A	0.27856 (16)	−0.07744 (14)	0.49621 (8)	0.0318 (3)
H3AA	0.2900	−0.1645	0.5161	0.038*
C4A	0.33233 (15)	−0.04861 (14)	0.42997 (8)	0.0301 (3)
C5A	0.31226 (14)	0.07552 (14)	0.39838 (7)	0.0245 (3)
H5AA	0.3472	0.0938	0.3522	0.029*
C6A	0.24091 (14)	0.17030 (13)	0.43558 (6)	0.0193 (2)
O1B	0.60822 (9)	0.83673 (9)	0.95805 (4)	0.01743 (16)
O2B	0.65404 (10)	0.61445 (9)	0.85595 (5)	0.02139 (18)
O3B	0.49768 (9)	0.66911 (8)	0.76153 (4)	0.01681 (16)
N1B	0.14290 (11)	0.41809 (11)	0.66309 (5)	0.0195 (2)
H1BD	0.1429	0.3307	0.6313	0.023*
C1B	0.7672 (2)	0.65985 (16)	1.04798 (8)	0.0374 (3)
H1BA	0.6537	0.6194	1.0317	0.056*
H1BB	0.7985	0.6305	1.0966	0.056*
H1BC	0.8215	0.6193	1.0099	0.056*
C2B	0.81046 (16)	0.83003 (14)	1.05690 (7)	0.0266 (3)
H2BA	0.9237	0.8703	1.0776	0.032*
H2BB	0.7522	0.8696	1.0941	0.032*
C3B	0.77559 (13)	0.88685 (13)	0.98354 (6)	0.0199 (2)
H3BA	0.8118	0.9984	0.9919	0.024*
H3BB	0.8303	0.8461	0.9450	0.024*
C4B	0.55382 (13)	0.83591 (12)	0.88023 (6)	0.0144 (2)
C5B	0.37558 (13)	0.80952 (12)	0.87150 (6)	0.0161 (2)
C6B	0.29341 (14)	0.72390 (13)	0.91802 (6)	0.0210 (2)
H6BA	0.3488	0.6901	0.9578	0.025*
C7B	0.13033 (15)	0.68740 (15)	0.90661 (7)	0.0270 (3)
H7BA	0.0751	0.6295	0.9389	0.032*
C8B	0.04823 (15)	0.73485 (14)	0.84858 (7)	0.0273 (3)
H8BA	−0.0630	0.7092	0.8408	0.033*
C9B	0.12932 (14)	0.82027 (14)	0.80174 (7)	0.0252 (3)
H9BA	0.0734	0.8531	0.7618	0.030*
C10B	0.29213 (14)	0.85778 (13)	0.81321 (6)	0.0195 (2)
H10A	0.3470	0.9167	0.7812	0.023*
C11B	0.63706 (13)	0.98164 (12)	0.85584 (6)	0.0154 (2)
C12B	0.60946 (14)	1.11664 (13)	0.88757 (6)	0.0211 (2)
H12A	0.5343	1.1146	0.9202	0.025*
C13B	0.69100 (16)	1.25303 (13)	0.87166 (7)	0.0256 (3)
H13A	0.6711	1.3440	0.8932	0.031*
C14B	0.80181 (16)	1.25757 (14)	0.82429 (7)	0.0272 (3)
H14A	0.8573	1.3513	0.8133	0.033*
C15B	0.83122 (15)	1.12444 (14)	0.79297 (7)	0.0239 (2)
H15A	0.9075	1.1270	0.7609	0.029*
C16B	0.74833 (13)	0.98724 (12)	0.80886 (6)	0.0178 (2)
H16A	0.7683	0.8964	0.7872	0.021*
C17B	0.57857 (12)	0.69440 (12)	0.83240 (6)	0.0154 (2)
C18B	0.48344 (13)	0.52459 (12)	0.71359 (6)	0.0174 (2)
H18A	0.5894	0.5082	0.7114	0.021*
C19B	0.38094 (14)	0.39610 (12)	0.74338 (7)	0.0199 (2)
H19A	0.3784	0.2990	0.7124	0.024*
H19B	0.4277	0.3959	0.7962	0.024*
C20B	0.21450 (14)	0.40916 (13)	0.74143 (6)	0.0208 (2)
H20A	0.1506	0.3204	0.7583	0.025*
H20B	0.2153	0.5006	0.7767	0.025*
C21B	−0.02218 (15)	0.42444 (16)	0.65909 (8)	0.0303 (3)
H21A	−0.0258	0.5157	0.6921	0.045*
H21B	−0.0833	0.3353	0.6758	0.045*
H21C	−0.0665	0.4264	0.6068	0.045*
C22B	0.23950 (15)	0.54977 (13)	0.63493 (7)	0.0216 (2)
H22A	0.2411	0.6449	0.6675	0.026*
H22B	0.1915	0.5522	0.5827	0.026*
C23B	0.40595 (14)	0.53774 (13)	0.63573 (6)	0.0208 (2)
H23A	0.4686	0.6280	0.6195	0.025*
H23B	0.4045	0.4482	0.5989	0.025*

	U11	U22	U33	U12	U13	U23
O1A	0.0261 (5)	0.0273 (5)	0.0207 (4)	0.0103 (4)	0.0027 (3)	0.0001 (3)
O2A	0.0526 (7)	0.0354 (6)	0.0290 (5)	−0.0030 (5)	0.0071 (5)	0.0090 (4)
O3A	0.0755 (9)	0.0329 (6)	0.0510 (7)	0.0041 (6)	−0.0062 (6)	0.0252 (5)
O4AA	0.0423 (8)	0.0202 (8)	0.102 (2)	0.0160 (7)	0.0016 (12)	−0.0015 (11)
O5AA	0.0380 (12)	0.0642 (18)	0.0363 (8)	0.0307 (12)	−0.0025 (7)	−0.0156 (9)
O4AB	0.0423 (8)	0.0202 (8)	0.102 (2)	0.0160 (7)	0.0016 (12)	−0.0015 (11)
O5AB	0.0380 (12)	0.0642 (18)	0.0363 (8)	0.0307 (12)	−0.0025 (7)	−0.0156 (9)
O6A	0.0272 (5)	0.0441 (6)	0.0212 (4)	0.0108 (4)	0.0046 (3)	0.0097 (4)
O7A	0.0551 (7)	0.0220 (5)	0.0306 (5)	0.0106 (4)	0.0009 (4)	0.0038 (4)
N1A	0.0361 (7)	0.0246 (6)	0.0310 (6)	−0.0054 (5)	−0.0104 (5)	0.0102 (5)
N2A	0.0293 (7)	0.0380 (8)	0.0613 (10)	0.0194 (6)	−0.0196 (6)	−0.0268 (7)
N3A	0.0211 (5)	0.0263 (5)	0.0227 (5)	0.0065 (4)	0.0027 (4)	0.0047 (4)
C1A	0.0157 (6)	0.0188 (5)	0.0193 (5)	0.0003 (4)	−0.0028 (4)	−0.0005 (4)
C2A	0.0237 (6)	0.0188 (6)	0.0262 (6)	−0.0017 (5)	−0.0060 (5)	0.0046 (5)
C3A	0.0273 (7)	0.0151 (6)	0.0443 (8)	0.0029 (5)	−0.0157 (6)	0.0011 (5)
C4A	0.0218 (7)	0.0225 (6)	0.0391 (7)	0.0102 (5)	−0.0103 (5)	−0.0119 (5)
C5A	0.0166 (6)	0.0296 (6)	0.0233 (6)	0.0075 (5)	−0.0028 (4)	−0.0060 (5)
C6A	0.0167 (6)	0.0183 (5)	0.0206 (5)	0.0051 (4)	−0.0018 (4)	−0.0003 (4)
O1B	0.0139 (4)	0.0227 (4)	0.0145 (4)	0.0038 (3)	0.0002 (3)	0.0038 (3)
O2B	0.0182 (4)	0.0180 (4)	0.0274 (4)	0.0073 (3)	−0.0006 (3)	0.0019 (3)
O3B	0.0179 (4)	0.0145 (4)	0.0164 (4)	0.0042 (3)	0.0014 (3)	−0.0011 (3)
N1B	0.0163 (5)	0.0198 (5)	0.0207 (5)	0.0043 (4)	0.0015 (4)	−0.0001 (4)
C1B	0.0476 (10)	0.0365 (8)	0.0302 (7)	0.0140 (7)	0.0002 (6)	0.0141 (6)
C2B	0.0267 (7)	0.0324 (7)	0.0197 (6)	0.0106 (5)	−0.0027 (5)	0.0024 (5)
C3B	0.0154 (6)	0.0198 (5)	0.0214 (5)	0.0028 (4)	−0.0035 (4)	0.0023 (4)
C4B	0.0133 (5)	0.0153 (5)	0.0140 (5)	0.0038 (4)	0.0010 (4)	0.0018 (4)
C5B	0.0141 (5)	0.0168 (5)	0.0159 (5)	0.0040 (4)	0.0022 (4)	−0.0019 (4)
C6B	0.0179 (6)	0.0241 (6)	0.0201 (5)	0.0043 (4)	0.0050 (4)	0.0020 (4)
C7B	0.0189 (6)	0.0306 (7)	0.0296 (6)	0.0020 (5)	0.0104 (5)	0.0018 (5)
C8B	0.0128 (6)	0.0315 (7)	0.0341 (7)	0.0058 (5)	0.0040 (5)	−0.0059 (5)
C9B	0.0180 (6)	0.0293 (6)	0.0271 (6)	0.0110 (5)	−0.0017 (4)	−0.0027 (5)
C10B	0.0170 (6)	0.0208 (5)	0.0206 (5)	0.0067 (4)	0.0025 (4)	0.0015 (4)
C11B	0.0133 (5)	0.0157 (5)	0.0155 (5)	0.0028 (4)	−0.0005 (4)	0.0022 (4)
C12B	0.0230 (6)	0.0185 (5)	0.0219 (6)	0.0068 (4)	0.0037 (4)	0.0012 (4)
C13B	0.0323 (7)	0.0151 (5)	0.0268 (6)	0.0055 (5)	0.0003 (5)	0.0006 (4)
C14B	0.0324 (7)	0.0186 (6)	0.0248 (6)	−0.0027 (5)	−0.0005 (5)	0.0069 (5)
C15B	0.0230 (6)	0.0254 (6)	0.0203 (6)	0.0000 (5)	0.0043 (4)	0.0051 (4)
C16B	0.0175 (6)	0.0170 (5)	0.0173 (5)	0.0029 (4)	0.0018 (4)	0.0017 (4)
C17B	0.0112 (5)	0.0142 (5)	0.0192 (5)	0.0008 (4)	0.0034 (4)	0.0018 (4)
C18B	0.0156 (5)	0.0144 (5)	0.0202 (5)	0.0036 (4)	0.0031 (4)	−0.0030 (4)
C19B	0.0185 (6)	0.0148 (5)	0.0239 (6)	0.0025 (4)	0.0002 (4)	0.0023 (4)
C20B	0.0184 (6)	0.0209 (6)	0.0208 (5)	0.0011 (4)	0.0035 (4)	0.0039 (4)
C21B	0.0181 (6)	0.0378 (7)	0.0335 (7)	0.0093 (5)	0.0012 (5)	0.0008 (6)
C22B	0.0249 (6)	0.0194 (5)	0.0194 (5)	0.0055 (5)	0.0010 (4)	0.0030 (4)
C23B	0.0228 (6)	0.0193 (5)	0.0175 (5)	0.0006 (4)	0.0062 (4)	−0.0002 (4)

O1A—C1A	1.2477 (14)	C4B—C17B	1.5543 (14)
O2A—N1A	1.2302 (16)	C5B—C6B	1.3901 (16)
O3A—N1A	1.2241 (15)	C5B—C10B	1.3962 (15)
O4AA—N2A	1.190 (4)	C6B—C7B	1.3927 (17)
O5AA—N2A	1.289 (4)	C6B—H6BA	0.9500
O4AB—N2A	1.632 (16)	C7B—C8B	1.3825 (19)
O5AB—N2A	0.876 (12)	C7B—H7BA	0.9500
O6A—N3A	1.2295 (12)	C8B—C9B	1.3891 (19)
O7A—N3A	1.2235 (13)	C8B—H8BA	0.9500
N1A—C2A	1.4580 (18)	C9B—C10B	1.3900 (17)
N2A—C4A	1.4501 (18)	C9B—H9BA	0.9500
N3A—C6A	1.4601 (15)	C10B—H10A	0.9500
C1A—C2A	1.4461 (17)	C11B—C16B	1.3869 (16)
C1A—C6A	1.4481 (16)	C11B—C12B	1.4004 (15)
C2A—C3A	1.3817 (19)	C12B—C13B	1.3840 (17)
C3A—C4A	1.382 (2)	C12B—H12A	0.9500
C3A—H3AA	0.9500	C13B—C14B	1.3892 (19)
C4A—C5A	1.3921 (19)	C13B—H13A	0.9500
C5A—C6A	1.3665 (16)	C14B—C15B	1.3901 (18)
C5A—H5AA	0.9500	C14B—H14A	0.9500
O1B—C4B	1.4243 (12)	C15B—C16B	1.3939 (16)
O1B—C3B	1.4431 (14)	C15B—H15A	0.9500
O2B—C17B	1.2013 (13)	C16B—H16A	0.9500
O3B—C17B	1.3450 (12)	C18B—C23B	1.5180 (16)
O3B—C18B	1.4647 (12)	C18B—C19B	1.5217 (16)
N1B—C21B	1.4838 (16)	C18B—H18A	1.0000
N1B—C20B	1.4961 (14)	C19B—C20B	1.5183 (17)
N1B—C22B	1.5039 (15)	C19B—H19A	0.9900
N1B—H1BD	0.9300	C19B—H19B	0.9900
C1B—C2B	1.5126 (19)	C20B—H20A	0.9900
C1B—H1BA	0.9800	C20B—H20B	0.9900
C1B—H1BB	0.9800	C21B—H21A	0.9800
C1B—H1BC	0.9800	C21B—H21B	0.9800
C2B—C3B	1.5140 (16)	C21B—H21C	0.9800
C2B—H2BA	0.9900	C22B—C23B	1.5175 (17)
C2B—H2BB	0.9900	C22B—H22A	0.9900
C3B—H3BA	0.9900	C22B—H22B	0.9900
C3B—H3BB	0.9900	C23B—H23A	0.9900
C4B—C11B	1.5259 (15)	C23B—H23B	0.9900
C4B—C5B	1.5339 (15)
O3A—N1A—O2A	122.35 (13)	C7B—C6B—H6BA	119.8
O3A—N1A—C2A	118.08 (13)	C8B—C7B—C6B	120.44 (12)
O2A—N1A—C2A	119.58 (11)	C8B—C7B—H7BA	119.8
O5AB—N2A—O4AA	104.2 (9)	C6B—C7B—H7BA	119.8
O5AB—N2A—O5AA	27.2 (10)	C7B—C8B—C9B	119.64 (11)
O4AA—N2A—O5AA	123.4 (2)	C7B—C8B—H8BA	120.2
O5AB—N2A—C4A	133.0 (8)	C9B—C8B—H8BA	120.2
O4AA—N2A—C4A	119.5 (3)	C8B—C9B—C10B	120.12 (11)
O5AA—N2A—C4A	117.02 (17)	C8B—C9B—H9BA	119.9
O5AB—N2A—O4AB	119.9 (9)	C10B—C9B—H9BA	119.9
O4AA—N2A—O4AB	15.8 (6)	C9B—C10B—C5B	120.47 (11)
O5AA—N2A—O4AB	138.1 (5)	C9B—C10B—H10A	119.8
C4A—N2A—O4AB	104.3 (6)	C5B—C10B—H10A	119.8
O7A—N3A—O6A	123.43 (10)	C16B—C11B—C12B	118.87 (10)
O7A—N3A—C6A	118.42 (10)	C16B—C11B—C4B	122.62 (9)
O6A—N3A—C6A	118.10 (10)	C12B—C11B—C4B	118.27 (10)
O1A—C1A—C2A	125.93 (11)	C13B—C12B—C11B	120.43 (11)
O1A—C1A—C6A	122.04 (10)	C13B—C12B—H12A	119.8
C2A—C1A—C6A	111.94 (10)	C11B—C12B—H12A	119.8
C3A—C2A—C1A	123.20 (12)	C12B—C13B—C14B	120.32 (11)
C3A—C2A—N1A	117.22 (11)	C12B—C13B—H13A	119.8
C1A—C2A—N1A	119.56 (12)	C14B—C13B—H13A	119.8
C2A—C3A—C4A	120.02 (12)	C13B—C14B—C15B	119.78 (11)
C2A—C3A—H3AA	120.0	C13B—C14B—H14A	120.1
C4A—C3A—H3AA	120.0	C15B—C14B—H14A	120.1
C3A—C4A—C5A	121.07 (12)	C14B—C15B—C16B	119.72 (11)
C3A—C4A—N2A	120.50 (13)	C14B—C15B—H15A	120.1
C5A—C4A—N2A	118.39 (14)	C16B—C15B—H15A	120.1
C6A—C5A—C4A	118.15 (12)	C11B—C16B—C15B	120.87 (10)
C6A—C5A—H5AA	120.9	C11B—C16B—H16A	119.6
C4A—C5A—H5AA	120.9	C15B—C16B—H16A	119.6
C5A—C6A—C1A	125.55 (11)	O2B—C17B—O3B	124.27 (10)
C5A—C6A—N3A	116.38 (11)	O2B—C17B—C4B	125.00 (10)
C1A—C6A—N3A	118.07 (10)	O3B—C17B—C4B	110.66 (8)
C4B—O1B—C3B	116.70 (8)	O3B—C18B—C23B	105.04 (8)
C17B—O3B—C18B	117.48 (8)	O3B—C18B—C19B	110.30 (9)
C21B—N1B—C20B	111.66 (9)	C23B—C18B—C19B	110.25 (9)
C21B—N1B—C22B	111.21 (9)	O3B—C18B—H18A	110.4
C20B—N1B—C22B	110.85 (9)	C23B—C18B—H18A	110.4
C21B—N1B—H1BD	107.6	C19B—C18B—H18A	110.4
C20B—N1B—H1BD	107.6	C20B—C19B—C18B	112.27 (9)
C22B—N1B—H1BD	107.6	C20B—C19B—H19A	109.1
C2B—C1B—H1BA	109.5	C18B—C19B—H19A	109.1
C2B—C1B—H1BB	109.5	C20B—C19B—H19B	109.1
H1BA—C1B—H1BB	109.5	C18B—C19B—H19B	109.1
C2B—C1B—H1BC	109.5	H19A—C19B—H19B	107.9
H1BA—C1B—H1BC	109.5	N1B—C20B—C19B	110.68 (9)
H1BB—C1B—H1BC	109.5	N1B—C20B—H20A	109.5
C1B—C2B—C3B	113.52 (10)	C19B—C20B—H20A	109.5
C1B—C2B—H2BA	108.9	N1B—C20B—H20B	109.5
C3B—C2B—H2BA	108.9	C19B—C20B—H20B	109.5
C1B—C2B—H2BB	108.9	H20A—C20B—H20B	108.1
C3B—C2B—H2BB	108.9	N1B—C21B—H21A	109.5
H2BA—C2B—H2BB	107.7	N1B—C21B—H21B	109.5
O1B—C3B—C2B	107.54 (10)	H21A—C21B—H21B	109.5
O1B—C3B—H3BA	110.2	N1B—C21B—H21C	109.5
C2B—C3B—H3BA	110.2	H21A—C21B—H21C	109.5
O1B—C3B—H3BB	110.2	H21B—C21B—H21C	109.5
C2B—C3B—H3BB	110.2	N1B—C22B—C23B	110.62 (9)
H3BA—C3B—H3BB	108.5	N1B—C22B—H22A	109.5
O1B—C4B—C11B	110.90 (8)	C23B—C22B—H22A	109.5
O1B—C4B—C5B	106.28 (8)	N1B—C22B—H22B	109.5
C11B—C4B—C5B	113.50 (8)	C23B—C22B—H22B	109.5
O1B—C4B—C17B	108.42 (8)	H22A—C22B—H22B	108.1
C11B—C4B—C17B	112.01 (9)	C22B—C23B—C18B	112.20 (9)
C5B—C4B—C17B	105.37 (8)	C22B—C23B—H23A	109.2
C6B—C5B—C10B	119.00 (10)	C18B—C23B—H23A	109.2
C6B—C5B—C4B	119.43 (10)	C22B—C23B—H23B	109.2
C10B—C5B—C4B	121.29 (10)	C18B—C23B—H23B	109.2
C5B—C6B—C7B	120.33 (11)	H23A—C23B—H23B	107.9
C5B—C6B—H6BA	119.8
O1A—C1A—C2A—C3A	174.36 (11)	C10B—C5B—C6B—C7B	−0.18 (16)
C6A—C1A—C2A—C3A	−2.28 (16)	C4B—C5B—C6B—C7B	−174.30 (10)
O1A—C1A—C2A—N1A	−4.32 (18)	C5B—C6B—C7B—C8B	0.50 (18)
C6A—C1A—C2A—N1A	179.04 (10)	C6B—C7B—C8B—C9B	−0.40 (18)
O3A—N1A—C2A—C3A	−15.05 (17)	C7B—C8B—C9B—C10B	−0.01 (18)
O2A—N1A—C2A—C3A	165.15 (12)	C8B—C9B—C10B—C5B	0.32 (17)
O3A—N1A—C2A—C1A	163.71 (12)	C6B—C5B—C10B—C9B	−0.22 (16)
O2A—N1A—C2A—C1A	−16.09 (17)	C4B—C5B—C10B—C9B	173.79 (10)
C1A—C2A—C3A—C4A	2.68 (19)	O1B—C4B—C11B—C16B	107.93 (11)
N1A—C2A—C3A—C4A	−178.61 (11)	C5B—C4B—C11B—C16B	−132.52 (10)
C2A—C3A—C4A—C5A	−2.15 (19)	C17B—C4B—C11B—C16B	−13.34 (13)
C2A—C3A—C4A—N2A	175.61 (11)	O1B—C4B—C11B—C12B	−66.41 (12)
O5AB—N2A—C4A—C3A	163.1 (14)	C5B—C4B—C11B—C12B	53.14 (12)
O4AA—N2A—C4A—C3A	7.5 (2)	C17B—C4B—C11B—C12B	172.32 (9)
O5AA—N2A—C4A—C3A	−169.72 (17)	C16B—C11B—C12B—C13B	0.58 (16)
O4AB—N2A—C4A—C3A	3.0 (6)	C4B—C11B—C12B—C13B	175.13 (10)
O5AB—N2A—C4A—C5A	−19.1 (15)	C11B—C12B—C13B—C14B	−0.33 (18)
O4AA—N2A—C4A—C5A	−174.66 (18)	C12B—C13B—C14B—C15B	−0.23 (18)
O5AA—N2A—C4A—C5A	8.1 (2)	C13B—C14B—C15B—C16B	0.52 (18)
O4AB—N2A—C4A—C5A	−179.2 (5)	C12B—C11B—C16B—C15B	−0.28 (16)
C3A—C4A—C5A—C6A	1.44 (18)	C4B—C11B—C16B—C15B	−174.59 (10)
N2A—C4A—C5A—C6A	−176.37 (11)	C14B—C15B—C16B—C11B	−0.26 (17)
C4A—C5A—C6A—C1A	−1.26 (18)	C18B—O3B—C17B—O2B	8.72 (16)
C4A—C5A—C6A—N3A	178.35 (11)	C18B—O3B—C17B—C4B	−168.41 (9)
O1A—C1A—C6A—C5A	−175.18 (11)	O1B—C4B—C17B—O2B	−11.26 (15)
C2A—C1A—C6A—C5A	1.61 (16)	C11B—C4B—C17B—O2B	111.44 (12)
O1A—C1A—C6A—N3A	5.21 (16)	C5B—C4B—C17B—O2B	−124.70 (11)
C2A—C1A—C6A—N3A	−178.00 (10)	O1B—C4B—C17B—O3B	165.86 (8)
O7A—N3A—C6A—C5A	−140.18 (12)	C11B—C4B—C17B—O3B	−71.45 (11)
O6A—N3A—C6A—C5A	37.65 (15)	C5B—C4B—C17B—O3B	52.41 (11)
O7A—N3A—C6A—C1A	39.47 (16)	C17B—O3B—C18B—C23B	−172.99 (9)
O6A—N3A—C6A—C1A	−142.70 (11)	C17B—O3B—C18B—C19B	68.22 (12)
C4B—O1B—C3B—C2B	−161.04 (9)	O3B—C18B—C19B—C20B	62.58 (12)
C1B—C2B—C3B—O1B	63.23 (14)	C23B—C18B—C19B—C20B	−52.98 (12)
C3B—O1B—C4B—C11B	−45.26 (11)	C21B—N1B—C20B—C19B	177.60 (9)
C3B—O1B—C4B—C5B	−169.05 (8)	C22B—N1B—C20B—C19B	−57.80 (12)
C3B—O1B—C4B—C17B	78.11 (11)	C18B—C19B—C20B—N1B	55.83 (12)
O1B—C4B—C5B—C6B	−30.91 (13)	C21B—N1B—C22B—C23B	−177.23 (9)
C11B—C4B—C5B—C6B	−153.07 (10)	C20B—N1B—C22B—C23B	57.92 (12)
C17B—C4B—C5B—C6B	84.02 (11)	N1B—C22B—C23B—C18B	−55.98 (12)
O1B—C4B—C5B—C10B	155.10 (9)	O3B—C18B—C23B—C22B	−65.73 (11)
C11B—C4B—C5B—C10B	32.95 (13)	C19B—C18B—C23B—C22B	53.09 (12)
C17B—C4B—C5B—C10B	−89.96 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1BD···O1A	0.93	1.81	2.6276 (12)	145
N1B—H1BD···O2A	0.93	2.33	3.0537 (15)	135
C20B—H20B···Cg2	0.99	2.77	3.7553 (13)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H1BD⋯O1A	0.93	1.81	2.6276 (12)	145
N1B—H1BD⋯O2A	0.93	2.33	3.0537 (15)	135
C20B—H20B⋯Cg2	0.99	2.77	3.7553 (13)	173

Cg2 is the centroid of the C5B–C10B ring.