Tramadolium picrate.

In the title salt {systematic name: [2-hy-droxy-3-(3-meth-oxy-phen-yl)cyclo-hexyl-meth-yl]dimethyl-aza-nium 2,4,6-trinitro-phenol-ate}, C(16)H(26)NO(2) (+)·C(6)H(2)N(3)O(7) (-), the cation is protonated at the N atom. The cyclo-hexane ring adopts a chair conformation with the hy-droxy substituent in an axial position. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link the cations and anions into supra-molecular chains along [100].

Related literature

For general background to tramadol, see: Scott & Perry (2000 ▶). For related tramadolium crystal structures, see: Bica et al. (2010 ▶); Siddaraju et al. (2011 ▶). For asymmetry parameters, see: Duax & Norton (1975 ▶). For the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C16H26NO2 +·C6H2N3O7 −

M = 492.48

Triclinic,

a = 8.5674 (10) Å

b = 12.3664 (12) Å

c = 13.2276 (13) Å

α = 113.003 (9)°

β = 107.686 (10)°

γ = 95.541 (9)°

V = 1191.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 295 K

0.35 × 0.2 × 0.15 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.974, T max = 1.000

8566 measured reflections

4838 independent reflections

3621 reflections with I > 2s(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.151

S = 1.02

4838 reflections

417 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004138/tk5053sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004138/tk5053Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004138/tk5053Isup3.cml

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

C16H26NO2+·C6H2N3O7−	Z = 2
Mr = 492.48	F(000) = 520
Triclinic, P1	Dx = 1.373 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 8.5674 (10) Å	Cell parameters from 3082 reflections
b = 12.3664 (12) Å	θ = 3.0–28.1°
c = 13.2276 (13) Å	µ = 0.11 mm−1
α = 113.003 (9)°	T = 295 K
β = 107.686 (10)°	Block, colourless
γ = 95.541 (9)°	0.35 × 0.2 × 0.15 mm
V = 1191.4 (2) Å3

Agilent Xcalibur Eos diffractometer	4838 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3621 reflections with I > 2s(I)
Graphite monochromator	Rint = 0.011
Detector resolution: 16.1544 pixels mm-1	θmax = 28.2°, θmin = 3.0°
ω–scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −15→11
Tmin = 0.974, Tmax = 1.000	l = −16→17
8566 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0712P)2 + 0.4321P] where P = (Fo2 + 2Fc2)/3
4838 reflections	(Δ/σ)max = 0.005
417 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.27 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
C1A	0.9734 (3)	0.89229 (17)	0.68387 (17)	0.0403 (4)
O1A	0.9951 (2)	1.00270 (12)	0.71283 (15)	0.0588 (4)
C2A	1.1124 (3)	0.83738 (17)	0.71022 (17)	0.0403 (4)
N2A	1.2837 (2)	0.91273 (16)	0.76034 (16)	0.0498 (4)
O21A	1.3924 (2)	0.8969 (2)	0.8330 (2)	0.0913 (7)
O22A	1.3123 (2)	0.98591 (15)	0.72350 (16)	0.0697 (5)
C3A	1.0940 (3)	0.71953 (19)	0.6920 (2)	0.0479 (5)
H3A1	1.190 (3)	0.691 (2)	0.713 (2)	0.068 (7)*
C4A	0.9333 (3)	0.64419 (18)	0.6403 (2)	0.0486 (5)
N4A	0.9126 (3)	0.51879 (18)	0.6183 (2)	0.0681 (6)
O41A	1.0393 (3)	0.48393 (19)	0.6489 (3)	0.1242 (11)
O42A	0.7713 (3)	0.45180 (16)	0.5689 (2)	0.0864 (6)
C5A	0.7912 (3)	0.68683 (19)	0.60864 (19)	0.0454 (5)
H5A1	0.685 (3)	0.638 (2)	0.5742 (19)	0.048 (6)*
C6A	0.8118 (3)	0.80560 (17)	0.62821 (17)	0.0414 (4)
N6A	0.6574 (3)	0.84536 (17)	0.59322 (17)	0.0565 (5)
O61A	0.6625 (2)	0.92878 (17)	0.56641 (18)	0.0814 (6)
O62A	0.5283 (3)	0.7920 (2)	0.5906 (2)	0.0943 (7)
C1	0.5866 (2)	0.31738 (17)	0.83219 (18)	0.0398 (4)
O1	0.43718 (17)	0.22657 (14)	0.74367 (15)	0.0520 (4)
H1	0.431 (4)	0.158 (3)	0.755 (3)	0.101 (11)*
C11	0.5844 (2)	0.42921 (17)	0.80911 (17)	0.0387 (4)
C12	0.7099 (3)	0.53512 (19)	0.8845 (2)	0.0461 (5)
H12	0.793 (3)	0.539 (2)	0.947 (2)	0.057 (7)*
C13	0.7053 (3)	0.64088 (18)	0.86989 (19)	0.0460 (5)
O13	0.8299 (2)	0.74161 (15)	0.95557 (17)	0.0739 (5)
C131	0.8202 (4)	0.8534 (2)	0.9519 (3)	0.0740 (8)
H13A	0.8344	0.8507	0.8818	0.089*
H13B	0.9077	0.9173	1.0205	0.089*
H13C	0.7119	0.8681	0.9510	0.089*
C14	0.5779 (3)	0.6393 (2)	0.77609 (19)	0.0469 (5)
H14	0.576 (3)	0.709 (2)	0.764 (2)	0.053 (6)*
C15	0.4555 (3)	0.5330 (2)	0.7000 (2)	0.0553 (6)
H15	0.363 (3)	0.528 (2)	0.632 (2)	0.065 (7)*
C16	0.4568 (3)	0.4293 (2)	0.7159 (2)	0.0507 (5)
H16	0.370 (3)	0.353 (2)	0.661 (2)	0.061 (7)*
C2	0.7448 (2)	0.26816 (17)	0.82194 (16)	0.0339 (4)
H2	0.838 (3)	0.3376 (19)	0.8804 (18)	0.041 (5)*
C21	0.7437 (2)	0.23599 (18)	0.69854 (17)	0.0390 (4)
H21A	0.746 (2)	0.3074 (19)	0.6776 (17)	0.042 (5)*
H21B	0.637 (3)	0.169 (2)	0.6343 (19)	0.047 (6)*
N22	0.8910 (2)	0.18804 (15)	0.67745 (15)	0.0403 (4)
H22	0.886 (3)	0.124 (2)	0.6850 (19)	0.050 (6)*
C23	1.0577 (3)	0.2729 (3)	0.7626 (3)	0.0607 (6)
H23A	1.056 (3)	0.349 (3)	0.759 (2)	0.080 (8)*
H23B	1.146 (4)	0.233 (3)	0.731 (3)	0.092 (9)*
H23C	1.071 (3)	0.284 (2)	0.846 (3)	0.073 (8)*
C24	0.8724 (5)	0.1546 (3)	0.5527 (3)	0.0727 (9)
H24A	0.876 (3)	0.227 (3)	0.536 (2)	0.079 (8)*
H24B	0.964 (4)	0.114 (3)	0.537 (3)	0.092 (9)*
H24C	0.755 (5)	0.097 (4)	0.500 (3)	0.129 (15)*
C3	0.7531 (3)	0.16293 (19)	0.8552 (2)	0.0431 (5)
H3A	0.663 (3)	0.095 (2)	0.796 (2)	0.052 (6)*
H3B	0.856 (3)	0.1377 (18)	0.8509 (17)	0.041 (5)*
C4	0.7468 (4)	0.1960 (3)	0.9774 (2)	0.0612 (7)
H4A	0.743 (3)	0.129 (2)	0.992 (2)	0.066 (7)*
H4B	0.852 (4)	0.265 (3)	1.044 (3)	0.081 (9)*
C5	0.5934 (4)	0.2432 (2)	0.9878 (3)	0.0597 (6)
H5A	0.599 (3)	0.270 (2)	1.071 (2)	0.066 (7)*
H5B	0.493 (4)	0.174 (3)	0.940 (2)	0.073 (8)*
C6	0.5841 (3)	0.3481 (2)	0.9559 (2)	0.0517 (5)
H6A	0.678 (3)	0.417 (2)	1.014 (2)	0.050 (6)*
H6B	0.481 (3)	0.378 (2)	0.961 (2)	0.059 (6)*

	U11	U22	U33	U12	U13	U23
C1A	0.0555 (12)	0.0352 (10)	0.0390 (10)	0.0203 (9)	0.0207 (9)	0.0206 (8)
O1A	0.0644 (10)	0.0318 (7)	0.0767 (11)	0.0196 (7)	0.0179 (8)	0.0252 (7)
C2A	0.0506 (11)	0.0348 (10)	0.0425 (10)	0.0151 (8)	0.0187 (9)	0.0218 (8)
N2A	0.0537 (11)	0.0411 (9)	0.0550 (10)	0.0141 (8)	0.0171 (9)	0.0236 (8)
O21A	0.0596 (11)	0.1014 (16)	0.1193 (17)	0.0151 (10)	0.0047 (11)	0.0776 (14)
O22A	0.0708 (11)	0.0561 (10)	0.0815 (12)	0.0009 (8)	0.0201 (9)	0.0393 (9)
C3A	0.0574 (13)	0.0408 (11)	0.0575 (13)	0.0232 (10)	0.0229 (11)	0.0299 (10)
C4A	0.0641 (13)	0.0336 (10)	0.0583 (13)	0.0171 (10)	0.0252 (11)	0.0273 (9)
N4A	0.0760 (15)	0.0414 (11)	0.0956 (16)	0.0172 (11)	0.0282 (13)	0.0409 (11)
O41A	0.0873 (15)	0.0650 (13)	0.233 (3)	0.0327 (12)	0.0346 (17)	0.0937 (17)
O42A	0.0896 (14)	0.0465 (10)	0.1185 (17)	0.0069 (10)	0.0238 (13)	0.0457 (11)
C5A	0.0544 (13)	0.0384 (11)	0.0448 (11)	0.0110 (10)	0.0186 (10)	0.0197 (9)
C6A	0.0509 (11)	0.0377 (10)	0.0404 (10)	0.0198 (9)	0.0180 (9)	0.0192 (8)
N6A	0.0557 (12)	0.0469 (10)	0.0601 (12)	0.0193 (9)	0.0122 (9)	0.0226 (9)
O61A	0.0756 (12)	0.0635 (11)	0.1009 (15)	0.0264 (10)	0.0071 (11)	0.0496 (11)
O62A	0.0577 (11)	0.1019 (16)	0.144 (2)	0.0319 (11)	0.0339 (12)	0.0747 (15)
C1	0.0372 (10)	0.0368 (10)	0.0487 (11)	0.0127 (8)	0.0204 (9)	0.0179 (9)
O1	0.0380 (7)	0.0442 (8)	0.0727 (10)	0.0099 (6)	0.0196 (7)	0.0256 (8)
C11	0.0431 (10)	0.0360 (9)	0.0471 (11)	0.0189 (8)	0.0276 (9)	0.0182 (8)
C12	0.0443 (11)	0.0494 (12)	0.0495 (12)	0.0198 (10)	0.0158 (10)	0.0261 (10)
C13	0.0446 (11)	0.0407 (11)	0.0565 (12)	0.0148 (9)	0.0210 (10)	0.0226 (10)
O13	0.0629 (10)	0.0461 (9)	0.0921 (13)	0.0018 (8)	0.0017 (10)	0.0336 (9)
C131	0.0787 (18)	0.0458 (13)	0.0875 (19)	0.0036 (12)	0.0190 (15)	0.0316 (13)
C14	0.0574 (13)	0.0442 (11)	0.0535 (12)	0.0249 (10)	0.0270 (11)	0.0281 (10)
C15	0.0611 (14)	0.0552 (13)	0.0488 (12)	0.0265 (11)	0.0150 (11)	0.0236 (11)
C16	0.0511 (12)	0.0459 (12)	0.0516 (12)	0.0181 (10)	0.0176 (10)	0.0178 (10)
C2	0.0339 (9)	0.0338 (9)	0.0391 (10)	0.0126 (8)	0.0170 (8)	0.0175 (8)
C21	0.0421 (10)	0.0413 (10)	0.0445 (11)	0.0213 (9)	0.0208 (9)	0.0237 (9)
N22	0.0523 (10)	0.0386 (9)	0.0508 (10)	0.0260 (8)	0.0314 (8)	0.0277 (8)
C23	0.0472 (13)	0.0650 (16)	0.090 (2)	0.0226 (12)	0.0360 (13)	0.0444 (15)
C24	0.122 (3)	0.0782 (19)	0.0646 (16)	0.062 (2)	0.0652 (19)	0.0459 (16)
C3	0.0503 (12)	0.0438 (11)	0.0523 (12)	0.0235 (10)	0.0287 (11)	0.0280 (10)
C4	0.0846 (18)	0.0710 (16)	0.0669 (16)	0.0406 (15)	0.0463 (15)	0.0500 (15)
C5	0.0804 (17)	0.0624 (15)	0.0678 (16)	0.0305 (14)	0.0517 (15)	0.0385 (13)
C6	0.0665 (15)	0.0490 (12)	0.0621 (14)	0.0274 (12)	0.0439 (13)	0.0284 (11)

C1A—O1A	1.243 (2)	C131—H13C	0.9600
C1A—C6A	1.444 (3)	C14—C15	1.378 (3)
C1A—C2A	1.446 (3)	C14—H14	0.94 (2)
C2A—C3A	1.365 (3)	C15—C16	1.379 (3)
C2A—N2A	1.457 (3)	C15—H15	0.98 (3)
N2A—O21A	1.211 (2)	C16—H16	0.99 (2)
N2A—O22A	1.221 (2)	C2—C21	1.518 (3)
C3A—C4A	1.383 (3)	C2—C3	1.529 (3)
C3A—H3A1	0.93 (3)	C2—H2	0.97 (2)
C4A—C5A	1.386 (3)	C21—N22	1.500 (2)
C4A—N4A	1.443 (3)	C21—H21A	1.02 (2)
N4A—O42A	1.216 (3)	C21—H21B	1.04 (2)
N4A—O41A	1.220 (3)	N22—C24	1.488 (3)
C5A—C6A	1.371 (3)	N22—C23	1.490 (3)
C5A—H5A1	0.91 (2)	N22—H22	0.84 (2)
C6A—N6A	1.462 (3)	C23—H23A	0.97 (3)
N6A—O61A	1.216 (3)	C23—H23B	1.04 (3)
N6A—O62A	1.216 (3)	C23—H23C	1.03 (3)
C1—O1	1.434 (2)	C24—H24A	1.01 (3)
C1—C11	1.529 (3)	C24—H24B	1.01 (3)
C1—C6	1.536 (3)	C24—H24C	1.02 (4)
C1—C2	1.559 (2)	C3—C4	1.524 (3)
O1—H1	0.92 (4)	C3—H3A	0.96 (2)
C11—C16	1.378 (3)	C3—H3B	0.97 (2)
C11—C12	1.386 (3)	C4—C5	1.510 (3)
C12—C13	1.397 (3)	C4—H4A	0.92 (3)
C12—H12	0.89 (2)	C4—H4B	1.05 (3)
C13—O13	1.371 (3)	C5—C6	1.515 (3)
C13—C14	1.373 (3)	C5—H5A	1.01 (3)
O13—C131	1.411 (3)	C5—H5B	0.99 (3)
C131—H13A	0.9600	C6—H6A	0.97 (2)
C131—H13B	0.9600	C6—H6B	1.00 (3)
O1A—C1A—C6A	125.64 (18)	C11—C16—H16	117.3 (14)
O1A—C1A—C2A	122.28 (19)	C15—C16—H16	122.6 (14)
C6A—C1A—C2A	111.98 (16)	C21—C2—C3	113.46 (15)
C3A—C2A—C1A	124.3 (2)	C21—C2—C1	108.86 (15)
C3A—C2A—N2A	117.66 (18)	C3—C2—C1	111.17 (15)
C1A—C2A—N2A	118.00 (16)	C21—C2—H2	110.4 (12)
O21A—N2A—O22A	122.9 (2)	C3—C2—H2	109.8 (12)
O21A—N2A—C2A	118.80 (18)	C1—C2—H2	102.6 (12)
O22A—N2A—C2A	118.19 (17)	N22—C21—C2	114.14 (15)
C2A—C3A—C4A	119.19 (19)	N22—C21—H21A	104.9 (11)
C2A—C3A—H3A1	119.3 (16)	C2—C21—H21A	113.9 (11)
C4A—C3A—H3A1	121.5 (16)	N22—C21—H21B	105.2 (12)
C3A—C4A—C5A	121.13 (19)	C2—C21—H21B	111.3 (12)
C3A—C4A—N4A	119.63 (19)	H21A—C21—H21B	106.7 (16)
C5A—C4A—N4A	119.2 (2)	C24—N22—C23	111.6 (2)
O42A—N4A—O41A	122.6 (2)	C24—N22—C21	109.29 (18)
O42A—N4A—C4A	119.4 (2)	C23—N22—C21	113.29 (17)
O41A—N4A—C4A	118.0 (2)	C24—N22—H22	106.7 (16)
C6A—C5A—C4A	119.0 (2)	C23—N22—H22	108.3 (16)
C6A—C5A—H5A1	119.3 (14)	C21—N22—H22	107.3 (16)
C4A—C5A—H5A1	121.8 (14)	N22—C23—H23A	106.9 (17)
C5A—C6A—C1A	124.27 (18)	N22—C23—H23B	104.6 (17)
C5A—C6A—N6A	116.47 (19)	H23A—C23—H23B	112 (2)
C1A—C6A—N6A	119.22 (17)	N22—C23—H23C	108.7 (15)
O61A—N6A—O62A	122.7 (2)	H23A—C23—H23C	110 (2)
O61A—N6A—C6A	119.0 (2)	H23B—C23—H23C	114 (2)
O62A—N6A—C6A	118.2 (2)	N22—C24—H24A	111.9 (16)
O1—C1—C11	106.66 (16)	N22—C24—H24B	108.4 (18)
O1—C1—C6	109.89 (17)	H24A—C24—H24B	111 (2)
C11—C1—C6	109.94 (16)	N22—C24—H24C	107 (2)
O1—C1—C2	109.06 (15)	H24A—C24—H24C	107 (3)
C11—C1—C2	111.76 (15)	H24B—C24—H24C	111 (3)
C6—C1—C2	109.49 (16)	C4—C3—C2	112.42 (18)
C1—O1—H1	110 (2)	C4—C3—H3A	111.1 (14)
C16—C11—C12	118.14 (19)	C2—C3—H3A	108.7 (14)
C16—C11—C1	121.59 (18)	C4—C3—H3B	111.0 (12)
C12—C11—C1	120.25 (18)	C2—C3—H3B	108.2 (12)
C11—C12—C13	121.5 (2)	H3A—C3—H3B	105.2 (18)
C11—C12—H12	121.1 (16)	C5—C4—C3	111.5 (2)
C13—C12—H12	117.4 (16)	C5—C4—H4A	108.5 (16)
O13—C13—C14	124.68 (19)	C3—C4—H4A	110.2 (16)
O13—C13—C12	115.64 (19)	C5—C4—H4B	106.0 (16)
C14—C13—C12	119.6 (2)	C3—C4—H4B	111.9 (16)
C13—O13—C131	117.77 (19)	H4A—C4—H4B	109 (2)
O13—C131—H13A	109.5	C4—C5—C6	111.4 (2)
O13—C131—H13B	109.5	C4—C5—H5A	108.8 (14)
H13A—C131—H13B	109.5	C6—C5—H5A	110.1 (15)
O13—C131—H13C	109.5	C4—C5—H5B	107.8 (16)
H13A—C131—H13C	109.5	C6—C5—H5B	114.4 (16)
H13B—C131—H13C	109.5	H5A—C5—H5B	104 (2)
C13—C14—C15	118.5 (2)	C5—C6—C1	113.27 (18)
C13—C14—H14	120.5 (14)	C5—C6—H6A	109.7 (14)
C15—C14—H14	121.0 (14)	C1—C6—H6A	108.8 (13)
C14—C15—C16	122.0 (2)	C5—C6—H6B	111.5 (14)
C14—C15—H15	121.1 (15)	C1—C6—H6B	108.6 (13)
C16—C15—H15	116.8 (15)	H6A—C6—H6B	104.6 (19)
C11—C16—C15	120.1 (2)
O1A—C1A—C2A—C3A	172.5 (2)	C6—C1—C11—C12	57.8 (2)
C6A—C1A—C2A—C3A	−4.0 (3)	C2—C1—C11—C12	−64.0 (2)
O1A—C1A—C2A—N2A	−7.1 (3)	C16—C11—C12—C13	2.3 (3)
C6A—C1A—C2A—N2A	176.48 (16)	C1—C11—C12—C13	−175.95 (17)
C3A—C2A—N2A—O21A	−35.3 (3)	C11—C12—C13—O13	175.22 (19)
C1A—C2A—N2A—O21A	144.2 (2)	C11—C12—C13—C14	−2.8 (3)
C3A—C2A—N2A—O22A	141.8 (2)	C14—C13—O13—C131	4.6 (3)
C1A—C2A—N2A—O22A	−38.6 (3)	C12—C13—O13—C131	−173.3 (2)
C1A—C2A—C3A—C4A	2.9 (3)	O13—C13—C14—C15	−176.5 (2)
N2A—C2A—C3A—C4A	−177.54 (18)	C12—C13—C14—C15	1.3 (3)
C2A—C3A—C4A—C5A	−1.0 (3)	C13—C14—C15—C16	0.5 (3)
C2A—C3A—C4A—N4A	178.7 (2)	C12—C11—C16—C15	−0.5 (3)
C3A—C4A—N4A—O42A	−177.3 (2)	C1—C11—C16—C15	177.77 (19)
C5A—C4A—N4A—O42A	2.3 (4)	C14—C15—C16—C11	−0.9 (3)
C3A—C4A—N4A—O41A	1.6 (4)	O1—C1—C2—C21	58.7 (2)
C5A—C4A—N4A—O41A	−178.7 (3)	C11—C1—C2—C21	−59.0 (2)
C3A—C4A—C5A—C6A	0.6 (3)	C6—C1—C2—C21	178.94 (17)
N4A—C4A—C5A—C6A	−179.1 (2)	O1—C1—C2—C3	−67.0 (2)
C4A—C5A—C6A—C1A	−2.1 (3)	C11—C1—C2—C3	175.30 (16)
C4A—C5A—C6A—N6A	−179.87 (18)	C6—C1—C2—C3	53.2 (2)
O1A—C1A—C6A—C5A	−172.8 (2)	C3—C2—C21—N22	−56.1 (2)
C2A—C1A—C6A—C5A	3.5 (3)	C1—C2—C21—N22	179.59 (16)
O1A—C1A—C6A—N6A	5.0 (3)	C2—C21—N22—C24	177.5 (2)
C2A—C1A—C6A—N6A	−178.72 (17)	C2—C21—N22—C23	−57.4 (2)
C5A—C6A—N6A—O61A	−152.9 (2)	C21—C2—C3—C4	−177.70 (19)
C1A—C6A—N6A—O61A	29.2 (3)	C1—C2—C3—C4	−54.6 (2)
C5A—C6A—N6A—O62A	26.1 (3)	C2—C3—C4—C5	54.9 (3)
C1A—C6A—N6A—O62A	−151.8 (2)	C3—C4—C5—C6	−54.4 (3)
O1—C1—C11—C16	−1.3 (2)	C4—C5—C6—C1	55.6 (3)
C6—C1—C11—C16	−120.4 (2)	O1—C1—C6—C5	65.3 (2)
C2—C1—C11—C16	117.8 (2)	C11—C1—C6—C5	−177.6 (2)
O1—C1—C11—C12	176.91 (16)	C2—C1—C6—C5	−54.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O22Ai	0.92 (4)	2.09 (4)	2.944 (2)	155 (3)
N22—H22···O1Aii	0.84 (2)	1.94 (2)	2.692 (2)	150 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O22Ai	0.92 (4)	2.09 (4)	2.944 (2)	155 (3)
N22—H22⋯O1Aii	0.84 (2)	1.94 (2)	2.692 (2)	150 (2)

Symmetry codes: (i) ; (ii) .