Orphenadrinium picrate picric acid.

The asymmetric unit of the title compound N,N-dimethyl-2-[(2-methyl-phen-yl)phenyl-meth-oxy]ethanaminium picrate picric acid, C(18)H(24)NO(+)·C(6)H(2)N(3)O(7) (-)·C(6)H(3)N(3)O(7), contains one orphenadrinium cation, one picrate anion and one picric acid mol-ecule. In the orphenadrine cation, the two aromatic rings form a dihedral angle of 70.30 (7)°. There is an intra-molecular O-H⋯O hydrogen bond in the picric acid mol-ecule, which generates an S(6) ring motif. In the crystal structure, the orphenadrine cations, picrate anions and picric acid mol-ecules are connected by strong inter-molecular N-H⋯O hydrogen bonds, π⋯π inter-actions between the benzene rings of cations and anions [centroid-centroid distance = 3.5603 (9) Å] and weak C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the efficiency of the anti­cholinergic drug orphenadrine (systematic name N,N-dimethyl-2-[(2-methyl­phen­yl)phenyl­meth­oxy]ethanamine), see: Hunskaar & Donnel (1991 ▶). For related structures, see: Glaser et al. (1992 ▶); Yathirajan et al. (2007 ▶). For details of hydrogen bonding, see: Jeffrey & Saenger (1991 ▶); Jeffrey (1997 ▶); Scheiner (1997 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H24NO+·C6H2N3O7 −·C6H3N3O7

M = 727.60

Monoclinic,

a = 11.1914 (9) Å

b = 12.4481 (10) Å

c = 22.6127 (19) Å

β = 93.601 (1)°

V = 3144.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.34 × 0.25 × 0.18 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.959, T max = 0.978

34841 measured reflections

9224 independent reflections

6851 reflections with I > 2s(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.127

S = 1.02

9224 reflections

480 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006379/ci5037sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006379/ci5037Isup2.hkl

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

C18H24NO+·C6H2N3O7−·C6H3N3O7	F(000) = 1512
Mr = 727.60	Dx = 1.537 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8774 reflections
a = 11.1914 (9) Å	θ = 2.4–30.0°
b = 12.4481 (10) Å	µ = 0.13 mm−1
c = 22.6127 (19) Å	T = 100 K
β = 93.601 (1)°	Block, yellow
V = 3144.0 (4) Å3	0.34 × 0.25 × 0.18 mm
Z = 4

Bruker APEX DUO CCD area-detector diffractometer	9224 independent reflections
Radiation source: fine-focus sealed tube	6851 reflections with I > 2s(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 30.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.959, Tmax = 0.978	k = −17→16
34841 measured reflections	l = −30→31

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) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0621P)2 + 1.1401P] where P = (Fo2 + 2Fc2)/3
9224 reflections	(Δ/σ)max = 0.001
480 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1A	0.29799 (8)	0.35411 (8)	0.45233 (4)	0.0182 (2)
O2A	0.26460 (9)	0.14380 (9)	0.43358 (6)	0.0318 (3)
O3A	0.08488 (11)	0.09425 (10)	0.41005 (8)	0.0455 (4)
O4A	−0.19368 (9)	0.32322 (10)	0.30733 (6)	0.0324 (3)
O5A	−0.16667 (10)	0.49561 (10)	0.30775 (6)	0.0312 (3)
O6A	0.19194 (10)	0.64682 (9)	0.40080 (5)	0.0255 (2)
O7A	0.34962 (9)	0.54552 (9)	0.40303 (5)	0.0236 (2)
N1A	0.16227 (10)	0.16434 (10)	0.41499 (6)	0.0193 (2)
N2A	−0.13373 (10)	0.40319 (11)	0.31998 (6)	0.0229 (3)
N3A	0.24039 (10)	0.55773 (10)	0.40000 (5)	0.0177 (2)
C1A	0.20748 (11)	0.36151 (11)	0.41721 (6)	0.0149 (3)
C2A	0.12853 (11)	0.27347 (11)	0.39928 (6)	0.0156 (3)
C3A	0.01861 (11)	0.28696 (12)	0.36858 (6)	0.0179 (3)
H3AA	−0.0302	0.2280	0.3596	0.021*
C4A	−0.01768 (11)	0.38852 (12)	0.35144 (6)	0.0180 (3)
C5A	0.05516 (12)	0.47732 (12)	0.36265 (6)	0.0177 (3)
H5AA	0.0303	0.5453	0.3500	0.021*
C6A	0.16441 (11)	0.46326 (11)	0.39269 (6)	0.0156 (3)
O1B	0.97430 (9)	0.90711 (9)	0.97661 (5)	0.0211 (2)
O2B	0.77967 (10)	0.99530 (9)	0.93846 (5)	0.0260 (2)
O3B	0.63236 (9)	0.90050 (9)	0.90035 (6)	0.0278 (3)
O4B	0.65060 (9)	0.52065 (9)	0.89499 (5)	0.0262 (2)
O5B	0.82135 (10)	0.43835 (9)	0.90729 (5)	0.0248 (2)
O6B	1.17444 (9)	0.64338 (9)	0.97116 (5)	0.0243 (2)
O7B	1.14073 (9)	0.78048 (9)	1.02692 (5)	0.0217 (2)
N1B	0.73404 (10)	0.90814 (10)	0.92275 (6)	0.0201 (2)
N2B	0.75924 (10)	0.51912 (10)	0.90699 (5)	0.0181 (2)
N3B	1.10999 (10)	0.71454 (10)	0.98881 (5)	0.0174 (2)
C1B	0.92362 (11)	0.81618 (11)	0.95787 (6)	0.0153 (3)
C2B	0.80552 (11)	0.81061 (11)	0.93132 (6)	0.0164 (3)
C3B	0.75193 (11)	0.71467 (12)	0.91434 (6)	0.0168 (3)
H3BA	0.6737	0.7129	0.8979	0.020*
C4B	0.81729 (11)	0.62166 (11)	0.92236 (6)	0.0159 (3)
C5B	0.93580 (11)	0.62156 (11)	0.94473 (6)	0.0161 (3)
H5BA	0.9799	0.5582	0.9475	0.019*
C6B	0.98593 (11)	0.71820 (11)	0.96275 (6)	0.0153 (3)
O8	0.41316 (8)	0.30752 (8)	0.32088 (4)	0.0186 (2)
N4	0.50481 (10)	0.24548 (10)	0.44887 (5)	0.0170 (2)
C7	0.49369 (13)	0.30347 (13)	0.19733 (7)	0.0230 (3)
H7A	0.4506	0.2408	0.2031	0.028*
C8	0.58017 (14)	0.30557 (16)	0.15569 (7)	0.0300 (4)
H8A	0.5954	0.2441	0.1340	0.036*
C9	0.64370 (14)	0.39915 (17)	0.14640 (7)	0.0341 (4)
H9A	0.7009	0.4006	0.1183	0.041*
C10	0.62187 (14)	0.48991 (17)	0.17894 (8)	0.0325 (4)
H10A	0.6643	0.5527	0.1727	0.039*
C11	0.53631 (13)	0.48776 (14)	0.22113 (7)	0.0247 (3)
H11A	0.5225	0.5490	0.2432	0.030*
C12	0.47145 (12)	0.39479 (12)	0.23045 (6)	0.0186 (3)
C13	0.38138 (11)	0.39039 (12)	0.27850 (6)	0.0174 (3)
H13A	0.3829	0.4596	0.2992	0.021*
C14	0.25466 (12)	0.37030 (12)	0.25284 (6)	0.0187 (3)
C15	0.18191 (13)	0.45666 (13)	0.23244 (6)	0.0217 (3)
C16	0.06643 (13)	0.43435 (15)	0.20804 (7)	0.0263 (3)
H16A	0.0179	0.4909	0.1944	0.032*
C17	0.02249 (13)	0.33060 (16)	0.20362 (7)	0.0286 (4)
H17A	−0.0545	0.3178	0.1873	0.034*
C18	0.09432 (13)	0.24604 (15)	0.22372 (7)	0.0262 (3)
H18A	0.0657	0.1760	0.2209	0.031*
C19	0.20997 (13)	0.26597 (13)	0.24823 (7)	0.0224 (3)
H19A	0.2578	0.2088	0.2617	0.027*
C20	0.52997 (12)	0.32655 (13)	0.34831 (7)	0.0230 (3)
H20A	0.5310	0.3945	0.3694	0.028*
H20B	0.5881	0.3304	0.3183	0.028*
C21	0.56231 (12)	0.23669 (12)	0.39088 (6)	0.0195 (3)
H21A	0.5389	0.1690	0.3723	0.023*
H21B	0.6486	0.2355	0.3985	0.023*
C22	0.51695 (13)	0.14244 (14)	0.48196 (7)	0.0270 (3)
H22A	0.4817	0.0855	0.4582	0.040*
H22B	0.4768	0.1480	0.5181	0.040*
H22C	0.6002	0.1273	0.4910	0.040*
C23	0.55619 (13)	0.33515 (14)	0.48613 (8)	0.0274 (3)
H23A	0.5169	0.3381	0.5226	0.041*
H23B	0.5445	0.4018	0.4653	0.041*
H23C	0.6403	0.3232	0.4945	0.041*
C24	0.22435 (15)	0.57185 (14)	0.23662 (8)	0.0297 (4)
H24A	0.1601	0.6189	0.2235	0.045*
H24B	0.2904	0.5815	0.2121	0.045*
H24C	0.2495	0.5882	0.2770	0.045*
H1N4	0.4270 (16)	0.2605 (15)	0.4420 (8)	0.022 (4)*
H1OB	0.914 (3)	0.964 (2)	0.9690 (13)	0.077 (9)*

	U11	U22	U33	U12	U13	U23
O1A	0.0146 (4)	0.0210 (5)	0.0186 (5)	0.0008 (4)	−0.0020 (4)	−0.0019 (4)
O2A	0.0215 (5)	0.0204 (6)	0.0521 (8)	0.0028 (4)	−0.0079 (5)	0.0023 (5)
O3A	0.0318 (6)	0.0223 (7)	0.0799 (11)	−0.0109 (5)	−0.0165 (7)	0.0081 (7)
O4A	0.0176 (5)	0.0352 (7)	0.0434 (7)	−0.0039 (5)	−0.0069 (5)	−0.0041 (6)
O5A	0.0226 (5)	0.0316 (7)	0.0383 (7)	0.0064 (5)	−0.0072 (5)	0.0054 (5)
O6A	0.0285 (5)	0.0156 (5)	0.0331 (6)	0.0009 (4)	0.0071 (5)	−0.0015 (4)
O7A	0.0166 (4)	0.0241 (6)	0.0300 (6)	−0.0042 (4)	0.0002 (4)	−0.0033 (5)
N1A	0.0167 (5)	0.0174 (6)	0.0238 (6)	−0.0011 (4)	0.0005 (4)	0.0002 (5)
N2A	0.0144 (5)	0.0309 (7)	0.0231 (6)	0.0014 (5)	−0.0012 (4)	−0.0009 (5)
N3A	0.0196 (5)	0.0179 (6)	0.0157 (6)	−0.0017 (4)	0.0026 (4)	−0.0022 (5)
C1A	0.0130 (5)	0.0173 (7)	0.0147 (6)	0.0000 (5)	0.0034 (4)	−0.0022 (5)
C2A	0.0144 (5)	0.0154 (7)	0.0171 (6)	0.0007 (5)	0.0021 (5)	−0.0002 (5)
C3A	0.0137 (5)	0.0208 (7)	0.0194 (7)	−0.0023 (5)	0.0028 (5)	−0.0026 (5)
C4A	0.0116 (5)	0.0240 (7)	0.0182 (7)	0.0005 (5)	−0.0012 (5)	−0.0004 (5)
C5A	0.0171 (6)	0.0193 (7)	0.0169 (6)	0.0033 (5)	0.0024 (5)	0.0010 (5)
C6A	0.0157 (5)	0.0157 (6)	0.0158 (6)	−0.0019 (5)	0.0033 (5)	−0.0019 (5)
O1B	0.0189 (4)	0.0162 (5)	0.0282 (6)	−0.0028 (4)	0.0020 (4)	−0.0043 (4)
O2B	0.0260 (5)	0.0148 (5)	0.0375 (7)	−0.0002 (4)	0.0045 (5)	−0.0014 (5)
O3B	0.0183 (5)	0.0240 (6)	0.0407 (7)	0.0041 (4)	−0.0022 (4)	0.0031 (5)
O4B	0.0192 (5)	0.0237 (6)	0.0346 (6)	−0.0067 (4)	−0.0071 (4)	0.0016 (5)
O5B	0.0277 (5)	0.0157 (5)	0.0304 (6)	0.0002 (4)	−0.0020 (4)	−0.0001 (4)
O6B	0.0175 (4)	0.0266 (6)	0.0289 (6)	0.0042 (4)	0.0022 (4)	−0.0047 (5)
O7B	0.0193 (4)	0.0233 (6)	0.0221 (5)	−0.0036 (4)	−0.0025 (4)	−0.0050 (4)
N1B	0.0188 (5)	0.0164 (6)	0.0254 (6)	0.0012 (4)	0.0046 (5)	0.0016 (5)
N2B	0.0203 (5)	0.0157 (6)	0.0179 (6)	−0.0031 (4)	−0.0013 (4)	0.0007 (5)
N3B	0.0149 (5)	0.0198 (6)	0.0174 (6)	−0.0019 (4)	0.0011 (4)	0.0002 (5)
C1B	0.0155 (5)	0.0156 (6)	0.0153 (6)	−0.0026 (5)	0.0043 (5)	−0.0011 (5)
C2B	0.0159 (5)	0.0153 (6)	0.0183 (6)	0.0015 (5)	0.0034 (5)	0.0005 (5)
C3B	0.0147 (5)	0.0190 (7)	0.0168 (6)	−0.0020 (5)	0.0015 (5)	0.0010 (5)
C4B	0.0181 (6)	0.0146 (6)	0.0149 (6)	−0.0033 (5)	0.0010 (5)	−0.0005 (5)
C5B	0.0171 (6)	0.0161 (6)	0.0151 (6)	0.0001 (5)	0.0014 (5)	0.0003 (5)
C6B	0.0126 (5)	0.0172 (6)	0.0160 (6)	−0.0015 (5)	0.0010 (4)	−0.0002 (5)
O8	0.0160 (4)	0.0225 (5)	0.0170 (5)	0.0011 (4)	−0.0023 (4)	0.0033 (4)
N4	0.0119 (5)	0.0211 (6)	0.0175 (6)	0.0006 (4)	−0.0019 (4)	−0.0009 (5)
C7	0.0231 (6)	0.0270 (8)	0.0187 (7)	0.0070 (6)	−0.0006 (5)	−0.0007 (6)
C8	0.0263 (7)	0.0432 (10)	0.0202 (7)	0.0137 (7)	−0.0004 (6)	−0.0055 (7)
C9	0.0198 (6)	0.0622 (13)	0.0205 (8)	0.0027 (7)	0.0033 (6)	−0.0003 (8)
C10	0.0247 (7)	0.0484 (11)	0.0242 (8)	−0.0097 (7)	0.0017 (6)	0.0040 (8)
C11	0.0236 (6)	0.0303 (8)	0.0200 (7)	−0.0031 (6)	0.0009 (6)	−0.0009 (6)
C12	0.0161 (5)	0.0246 (7)	0.0149 (6)	0.0044 (5)	−0.0009 (5)	0.0012 (5)
C13	0.0177 (6)	0.0191 (7)	0.0152 (6)	0.0031 (5)	0.0007 (5)	0.0008 (5)
C14	0.0170 (6)	0.0251 (7)	0.0140 (6)	0.0042 (5)	0.0024 (5)	−0.0003 (5)
C15	0.0211 (6)	0.0290 (8)	0.0151 (6)	0.0075 (6)	0.0031 (5)	0.0019 (6)
C16	0.0199 (6)	0.0407 (10)	0.0184 (7)	0.0111 (6)	0.0018 (5)	0.0033 (6)
C17	0.0172 (6)	0.0504 (11)	0.0180 (7)	0.0016 (6)	0.0001 (5)	−0.0016 (7)
C18	0.0230 (7)	0.0350 (9)	0.0207 (7)	−0.0049 (6)	0.0019 (6)	−0.0037 (7)
C19	0.0217 (6)	0.0259 (8)	0.0195 (7)	0.0027 (6)	0.0006 (5)	−0.0008 (6)
C20	0.0170 (6)	0.0291 (8)	0.0224 (7)	−0.0016 (6)	−0.0038 (5)	0.0061 (6)
C21	0.0173 (6)	0.0238 (7)	0.0172 (7)	0.0054 (5)	−0.0001 (5)	0.0000 (6)
C22	0.0224 (7)	0.0326 (9)	0.0259 (8)	0.0047 (6)	0.0007 (6)	0.0110 (7)
C23	0.0172 (6)	0.0350 (9)	0.0294 (8)	−0.0003 (6)	−0.0026 (6)	−0.0137 (7)
C24	0.0345 (8)	0.0284 (9)	0.0261 (8)	0.0094 (7)	0.0003 (6)	0.0032 (7)

O1A—C1A	1.2507 (16)	N4—C21	1.5004 (18)
O2A—N1A	1.2219 (15)	N4—H1N4	0.894 (18)
O3A—N1A	1.2296 (16)	C7—C12	1.392 (2)
O4A—N2A	1.2243 (18)	C7—C8	1.392 (2)
O5A—N2A	1.2342 (18)	C7—H7A	0.93
O6A—N3A	1.2351 (16)	C8—C9	1.388 (3)
O7A—N3A	1.2295 (15)	C8—H8A	0.93
N1A—C2A	1.4482 (18)	C9—C10	1.378 (3)
N2A—C4A	1.4527 (17)	C9—H9A	0.93
N3A—C6A	1.4545 (18)	C10—C11	1.394 (2)
C1A—C2A	1.4495 (19)	C10—H10A	0.93
C1A—C6A	1.4528 (19)	C11—C12	1.389 (2)
C2A—C3A	1.3842 (18)	C11—H11A	0.93
C3A—C4A	1.376 (2)	C12—C13	1.5288 (19)
C3A—H3AA	0.93	C13—C14	1.5188 (19)
C4A—C5A	1.387 (2)	C13—H13A	0.98
C5A—C6A	1.3720 (19)	C14—C19	1.393 (2)
C5A—H5AA	0.93	C14—C15	1.409 (2)
O1B—C1B	1.3237 (17)	C15—C16	1.401 (2)
O1B—H1OB	0.99 (3)	C15—C24	1.512 (2)
O2B—N1B	1.2416 (17)	C16—C17	1.383 (3)
O3B—N1B	1.2200 (16)	C16—H16A	0.93
O4B—N2B	1.2290 (15)	C17—C18	1.384 (2)
O5B—N2B	1.2222 (16)	C17—H17A	0.93
O6B—N3B	1.2249 (15)	C18—C19	1.398 (2)
O7B—N3B	1.2238 (16)	C18—H18A	0.93
N1B—C2B	1.4601 (18)	C19—H19A	0.93
N2B—C4B	1.4642 (18)	C20—C21	1.505 (2)
N3B—C6B	1.4745 (16)	C20—H20A	0.97
C1B—C6B	1.4059 (19)	C20—H20B	0.97
C1B—C2B	1.4186 (18)	C21—H21A	0.97
C2B—C3B	1.380 (2)	C21—H21B	0.97
C3B—C4B	1.3754 (19)	C22—H22A	0.96
C3B—H3BA	0.93	C22—H22B	0.96
C4B—C5B	1.3895 (18)	C22—H22C	0.96
C5B—C6B	1.3782 (19)	C23—H23A	0.96
C5B—H5BA	0.93	C23—H23B	0.96
O8—C20	1.4311 (16)	C23—H23C	0.96
O8—C13	1.4375 (17)	C24—H24A	0.96
N4—C22	1.487 (2)	C24—H24B	0.96
N4—C23	1.4919 (19)	C24—H24C	0.96
O2A—N1A—O3A	121.49 (13)	C7—C8—H8A	119.9
O2A—N1A—C2A	120.33 (12)	C10—C9—C8	119.84 (15)
O3A—N1A—C2A	118.17 (12)	C10—C9—H9A	120.1
O4A—N2A—O5A	123.64 (12)	C8—C9—H9A	120.1
O4A—N2A—C4A	118.18 (13)	C9—C10—C11	120.14 (17)
O5A—N2A—C4A	118.18 (13)	C9—C10—H10A	119.9
O7A—N3A—O6A	123.09 (12)	C11—C10—H10A	119.9
O7A—N3A—C6A	118.59 (12)	C12—C11—C10	120.51 (16)
O6A—N3A—C6A	118.27 (11)	C12—C11—H11A	119.7
O1A—C1A—C2A	125.25 (13)	C10—C11—H11A	119.7
O1A—C1A—C6A	122.86 (12)	C11—C12—C7	119.07 (13)
C2A—C1A—C6A	111.75 (11)	C11—C12—C13	120.78 (13)
C3A—C2A—N1A	116.53 (12)	C7—C12—C13	120.08 (13)
C3A—C2A—C1A	123.74 (13)	O8—C13—C14	108.81 (11)
N1A—C2A—C1A	119.71 (11)	O8—C13—C12	110.66 (11)
C4A—C3A—C2A	119.34 (13)	C14—C13—C12	112.08 (11)
C4A—C3A—H3AA	120.3	O8—C13—H13A	108.4
C2A—C3A—H3AA	120.3	C14—C13—H13A	108.4
C3A—C4A—C5A	121.39 (12)	C12—C13—H13A	108.4
C3A—C4A—N2A	119.50 (13)	C19—C14—C15	119.31 (13)
C5A—C4A—N2A	119.10 (13)	C19—C14—C13	120.28 (13)
C6A—C5A—C4A	118.94 (13)	C15—C14—C13	120.40 (13)
C6A—C5A—H5AA	120.5	C16—C15—C14	118.53 (15)
C4A—C5A—H5AA	120.5	C16—C15—C24	119.42 (14)
C5A—C6A—C1A	124.35 (12)	C14—C15—C24	122.04 (13)
C5A—C6A—N3A	116.71 (12)	C17—C16—C15	121.91 (15)
C1A—C6A—N3A	118.94 (11)	C17—C16—H16A	119.0
C1B—O1B—H1OB	106.4 (17)	C15—C16—H16A	119.0
O3B—N1B—O2B	122.90 (12)	C16—C17—C18	119.33 (14)
O3B—N1B—C2B	118.64 (12)	C16—C17—H17A	120.3
O2B—N1B—C2B	118.47 (12)	C18—C17—H17A	120.3
O5B—N2B—O4B	124.64 (12)	C17—C18—C19	119.97 (16)
O5B—N2B—C4B	118.17 (11)	C17—C18—H18A	120.0
O4B—N2B—C4B	117.19 (12)	C19—C18—H18A	120.0
O7B—N3B—O6B	124.70 (12)	C14—C19—C18	120.94 (15)
O7B—N3B—C6B	118.47 (11)	C14—C19—H19A	119.5
O6B—N3B—C6B	116.81 (12)	C18—C19—H19A	119.5
O1B—C1B—C6B	121.08 (12)	O8—C20—C21	109.30 (12)
O1B—C1B—C2B	123.12 (12)	O8—C20—H20A	109.8
C6B—C1B—C2B	115.80 (12)	C21—C20—H20A	109.8
C3B—C2B—C1B	122.49 (13)	O8—C20—H20B	109.8
C3B—C2B—N1B	117.24 (12)	C21—C20—H20B	109.8
C1B—C2B—N1B	120.24 (12)	H20A—C20—H20B	108.3
C4B—C3B—C2B	118.26 (12)	N4—C21—C20	113.93 (12)
C4B—C3B—H3BA	120.9	N4—C21—H21A	108.8
C2B—C3B—H3BA	120.9	C20—C21—H21A	108.8
C3B—C4B—C5B	122.44 (13)	N4—C21—H21B	108.8
C3B—C4B—N2B	118.56 (12)	C20—C21—H21B	108.8
C5B—C4B—N2B	119.00 (12)	H21A—C21—H21B	107.7
C6B—C5B—C4B	117.94 (13)	N4—C22—H22A	109.5
C6B—C5B—H5BA	121.0	N4—C22—H22B	109.5
C4B—C5B—H5BA	121.0	H22A—C22—H22B	109.5
C5B—C6B—C1B	122.91 (12)	N4—C22—H22C	109.5
C5B—C6B—N3B	116.54 (12)	H22A—C22—H22C	109.5
C1B—C6B—N3B	120.54 (12)	H22B—C22—H22C	109.5
C20—O8—C13	110.56 (11)	N4—C23—H23A	109.5
C22—N4—C23	109.96 (12)	N4—C23—H23B	109.5
C22—N4—C21	110.26 (12)	H23A—C23—H23B	109.5
C23—N4—C21	112.14 (12)	N4—C23—H23C	109.5
C22—N4—H1N4	108.9 (12)	H23A—C23—H23C	109.5
C23—N4—H1N4	106.1 (12)	H23B—C23—H23C	109.5
C21—N4—H1N4	109.3 (12)	C15—C24—H24A	109.5
C12—C7—C8	120.25 (16)	C15—C24—H24B	109.5
C12—C7—H7A	119.9	H24A—C24—H24B	109.5
C8—C7—H7A	119.9	C15—C24—H24C	109.5
C9—C8—C7	120.18 (16)	H24A—C24—H24C	109.5
C9—C8—H8A	119.9	H24B—C24—H24C	109.5
O2A—N1A—C2A—C3A	168.43 (13)	N2B—C4B—C5B—C6B	−175.54 (12)
O3A—N1A—C2A—C3A	−12.8 (2)	C4B—C5B—C6B—C1B	−1.9 (2)
O2A—N1A—C2A—C1A	−13.2 (2)	C4B—C5B—C6B—N3B	177.26 (12)
O3A—N1A—C2A—C1A	165.56 (14)	O1B—C1B—C6B—C5B	178.87 (13)
O1A—C1A—C2A—C3A	168.56 (13)	C2B—C1B—C6B—C5B	−1.84 (19)
C6A—C1A—C2A—C3A	−7.27 (18)	O1B—C1B—C6B—N3B	−0.22 (19)
O1A—C1A—C2A—N1A	−9.7 (2)	C2B—C1B—C6B—N3B	179.08 (11)
C6A—C1A—C2A—N1A	174.46 (11)	O7B—N3B—C6B—C5B	−148.70 (13)
N1A—C2A—C3A—C4A	−178.86 (12)	O6B—N3B—C6B—C5B	29.92 (17)
C1A—C2A—C3A—C4A	2.8 (2)	O7B—N3B—C6B—C1B	30.44 (18)
C2A—C3A—C4A—C5A	2.0 (2)	O6B—N3B—C6B—C1B	−150.94 (13)
C2A—C3A—C4A—N2A	−179.11 (12)	C12—C7—C8—C9	−0.8 (2)
O4A—N2A—C4A—C3A	−3.2 (2)	C7—C8—C9—C10	0.6 (2)
O5A—N2A—C4A—C3A	176.42 (13)	C8—C9—C10—C11	0.1 (3)
O4A—N2A—C4A—C5A	175.66 (13)	C9—C10—C11—C12	−0.6 (2)
O5A—N2A—C4A—C5A	−4.7 (2)	C10—C11—C12—C7	0.4 (2)
C3A—C4A—C5A—C6A	−1.5 (2)	C10—C11—C12—C13	177.33 (14)
N2A—C4A—C5A—C6A	179.62 (12)	C8—C7—C12—C11	0.3 (2)
C4A—C5A—C6A—C1A	−3.9 (2)	C8—C7—C12—C13	−176.63 (13)
C4A—C5A—C6A—N3A	176.24 (12)	C20—O8—C13—C14	−177.11 (11)
O1A—C1A—C6A—C5A	−168.09 (13)	C20—O8—C13—C12	59.33 (15)
C2A—C1A—C6A—C5A	7.87 (18)	C11—C12—C13—O8	−120.56 (14)
O1A—C1A—C6A—N3A	11.76 (19)	C7—C12—C13—O8	56.29 (17)
C2A—C1A—C6A—N3A	−172.28 (11)	C11—C12—C13—C14	117.78 (15)
O7A—N3A—C6A—C5A	−150.15 (13)	C7—C12—C13—C14	−65.37 (17)
O6A—N3A—C6A—C5A	27.39 (18)	O8—C13—C14—C19	−29.84 (17)
O7A—N3A—C6A—C1A	29.99 (18)	C12—C13—C14—C19	92.88 (16)
O6A—N3A—C6A—C1A	−152.48 (12)	O8—C13—C14—C15	151.37 (13)
O1B—C1B—C2B—C3B	−177.10 (13)	C12—C13—C14—C15	−85.91 (16)
C6B—C1B—C2B—C3B	3.62 (19)	C19—C14—C15—C16	0.0 (2)
O1B—C1B—C2B—N1B	0.8 (2)	C13—C14—C15—C16	178.78 (12)
C6B—C1B—C2B—N1B	−178.46 (12)	C19—C14—C15—C24	179.42 (14)
O3B—N1B—C2B—C3B	−1.22 (19)	C13—C14—C15—C24	−1.8 (2)
O2B—N1B—C2B—C3B	178.99 (13)	C14—C15—C16—C17	0.1 (2)
O3B—N1B—C2B—C1B	−179.25 (13)	C24—C15—C16—C17	−179.37 (14)
O2B—N1B—C2B—C1B	0.97 (19)	C15—C16—C17—C18	−0.1 (2)
C1B—C2B—C3B—C4B	−1.6 (2)	C16—C17—C18—C19	0.1 (2)
N1B—C2B—C3B—C4B	−179.57 (12)	C15—C14—C19—C18	0.0 (2)
C2B—C3B—C4B—C5B	−2.4 (2)	C13—C14—C19—C18	−178.82 (13)
C2B—C3B—C4B—N2B	177.23 (12)	C17—C18—C19—C14	0.0 (2)
O5B—N2B—C4B—C3B	171.21 (13)	C13—O8—C20—C21	−178.14 (12)
O4B—N2B—C4B—C3B	−9.23 (19)	C22—N4—C21—C20	166.36 (12)
O5B—N2B—C4B—C5B	−9.11 (19)	C23—N4—C21—C20	−70.75 (15)
O4B—N2B—C4B—C5B	170.45 (12)	O8—C20—C21—N4	−78.40 (16)
C3B—C4B—C5B—C6B	4.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···O1A	0.90 (2)	1.88 (2)	2.6860 (15)	149 (2)
N4—H1N4···O2A	0.90 (2)	2.32 (2)	2.9718 (16)	129 (2)
O1B—H1OB···O2B	0.99 (3)	1.66 (3)	2.5412 (15)	146 (3)
C5B—H5BA···O3Ai	0.93	2.41	3.2833 (19)	156
C9—H9A···O6Bii	0.93	2.59	3.4884 (19)	163
C20—H20B···O4Aiii	0.97	2.47	3.2841 (17)	141
C23—H23C···O7Biv	0.96	2.58	3.4901 (18)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1N4⋯O1A	0.90 (2)	1.88 (2)	2.6860 (15)	149 (2)
N4—H1N4⋯O2A	0.90 (2)	2.32 (2)	2.9718 (16)	129 (2)
O1B—H1OB⋯O2B	0.99 (3)	1.66 (3)	2.5412 (15)	146 (3)
C5B—H5BA⋯O3Ai	0.93	2.41	3.2833 (19)	156
C9—H9A⋯O6Bii	0.93	2.59	3.4884 (19)	163
C20—H20B⋯O4Aiii	0.97	2.47	3.2841 (17)	141
C23—H23C⋯O7Biv	0.96	2.58	3.4901 (18)	158

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