(3S,4S)-3-Ethyl-4-hydr-oxy-3-(3-methoxy-phen-yl)-1-methyl-azepan-1-ium d-tartrate dihydrate.

In the title compound, C(16)H(26)NO(2) (+)·C(4)H(5)O(6) (-)·2H(2)O, a meptaz-inol derivative, three C atoms of the azepane ring are disordered over two positions, with site-occupancy factors of 0.80 and 0.20; the major disorder component adopts a twist-chair conformation, while the minor component has a chair conformation. The benzene ring is axially substituted on the heterocyclic ring, resulting in a folded conformation of the cation. The absolute configuration was determined with reference to d-tartaric acid. The crystal structure is stabilized by an extensive network of intra- and inter-molecular O-H⋯O hydrogen bonds.

Related literature

For the synthesis of the racemate of the title compound, see: Hao et al. (2005 ▶). For conformational studies of seven-membered rings, see: Eliel et al. (1994 ▶); Entrena et al. (2005 ▶). For the analgesic activity and clinical use of meptazinol, see: Holmes (1985 ▶). For related literature, see: Bill et al. (1983 ▶).

Experimental

Crystal data

C16H26NO2 +·C4H5O6 −·2H2O

M = 449.49

Orthorhombic,

a = 7.146 (3) Å

b = 10.812 (4) Å

c = 29.338 (11) Å

V = 2266.7 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.20 × 0.15 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.988

11334 measured reflections

2855 independent reflections

2173 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.163

S = 1.04

2855 reflections

319 parameters

19 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005898/wn2243sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005898/wn2243Isup2.hkl

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

C16H26NO2+·C4H5O6–·2H2O	F000 = 968
Mr = 449.49	Dx = 1.317 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1000 reflections
a = 7.146 (3) Å	θ = 2.8–22.5º
b = 10.812 (4) Å	µ = 0.11 mm−1
c = 29.338 (11) Å	T = 293 (2) K
V = 2266.7 (15) Å3	Prismatic, colorless
Z = 4	0.20 × 0.15 × 0.12 mm

Bruker SMART APEX CCD area-detector diffractometer	2855 independent reflections
Radiation source: fine-focus sealed tube	2173 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.076
T = 293(2) K	θmax = 27.1º
φ and ω scans	θmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→4
Tmin = 0.979, Tmax = 0.988	k = −13→13
11334 measured reflections	l = −37→37

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)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.0771P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2855 reflections	Δρmax = 0.43 e Å−3
319 parameters	Δρmin = −0.26 e Å−3
19 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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)
O1	−1.0175 (7)	0.3641 (4)	0.46124 (12)	0.0684 (12)
H1X	−1.114 (7)	0.405 (6)	0.457 (2)	0.14 (4)*
O2	−0.7001 (6)	0.4436 (3)	0.25255 (10)	0.0628 (11)
O3	−0.6276 (4)	0.1543 (3)	0.13391 (10)	0.0425 (7)
H3	−0.7400	0.1418	0.1307	0.064*
O4	−0.6399 (5)	0.2140 (4)	0.06130 (12)	0.0626 (10)
O5	−0.2757 (4)	0.2069 (3)	0.05050 (10)	0.0487 (8)
H5	−0.3605	0.2365	0.0352	0.073*
O6	−0.3086 (4)	0.3996 (3)	0.11490 (10)	0.0430 (7)
H6	−0.3766	0.4310	0.1342	0.065*
O7	0.0443 (4)	0.3653 (3)	0.13158 (11)	0.0480 (8)
O8	0.0205 (4)	0.1619 (3)	0.13574 (10)	0.0391 (7)
O9	−0.6223 (5)	0.4527 (3)	0.15827 (12)	0.0473 (8)
H9X	−0.651 (9)	0.457 (5)	0.1855 (9)	0.066 (17)*
H9Y	−0.721 (6)	0.424 (7)	0.147 (2)	0.11 (3)*
O10	0.0604 (5)	0.1148 (3)	0.01603 (11)	0.0472 (8)
H10X	−0.033 (5)	0.142 (5)	0.0284 (18)	0.067 (18)*
H10Y	0.121 (8)	0.135 (6)	0.0387 (14)	0.08 (2)*
N1	−0.9584 (7)	0.0649 (3)	0.42832 (11)	0.0451 (10)
H1	−0.925 (6)	0.018 (3)	0.4048 (10)	0.029 (11)*
C2	−1.0991 (6)	0.1554 (4)	0.41055 (14)	0.0381 (9)
H2A	−1.1746	0.1816	0.4363	0.046*
H2B	−1.1814	0.1103	0.3902	0.046*
C3	−1.0364 (6)	0.2740 (4)	0.38507 (13)	0.0340 (9)
C4	−0.9242 (8)	0.3610 (4)	0.41797 (14)	0.0480 (12)
H4	−0.9289	0.4447	0.4052	0.058*
C5A	−0.7183 (8)	0.3276 (5)	0.42468 (16)	0.0575 (13)	0.80
H5A	−0.6738	0.3677	0.4522	0.069*	0.80
H5B	−0.6473	0.3609	0.3993	0.069*	0.80
C6A	−0.6754 (8)	0.1822 (6)	0.42849 (18)	0.0489 (15)	0.80
H6A	−0.6734	0.1480	0.3979	0.059*	0.80
H6B	−0.5509	0.1721	0.4412	0.059*	0.80
C7A	−0.8041 (9)	0.1098 (5)	0.4556 (2)	0.0691 (15)	0.80
H7A	−0.8522	0.1602	0.4803	0.083*	0.80
H7B	−0.7382	0.0401	0.4689	0.083*	0.80
C5B	−0.7183 (8)	0.3276 (5)	0.42468 (16)	0.0575 (13)	0.20
H5B1	−0.6630	0.2960	0.3968	0.069*	0.20
H5B2	−0.6463	0.3980	0.4353	0.069*	0.20
C6B	−0.730 (4)	0.2392 (14)	0.4568 (5)	0.049 (6)	0.20
H6B1	−0.7994	0.2782	0.4814	0.058*	0.20
H6B2	−0.6033	0.2304	0.4680	0.058*	0.20
C7B	−0.8041 (9)	0.1098 (5)	0.4556 (2)	0.0691 (15)	0.20
H7B1	−0.6980	0.0580	0.4477	0.083*	0.20
H7B2	−0.8358	0.0895	0.4869	0.083*	0.20
C8	−1.0659 (12)	−0.0250 (5)	0.45936 (18)	0.082 (2)
H8A	−0.9931	−0.0986	0.4638	0.123*
H8B	−1.1831	−0.0462	0.4454	0.123*
H8C	−1.0888	0.0136	0.4883	0.123*
C9	−1.2199 (7)	0.3436 (5)	0.37375 (18)	0.0567 (13)
H9A	−1.2956	0.3471	0.4012	0.068*
H9B	−1.1882	0.4280	0.3656	0.068*
C10	−1.3354 (9)	0.2906 (7)	0.3367 (2)	0.0770 (18)
H10A	−1.2604	0.2814	0.3097	0.116*
H10B	−1.4386	0.3448	0.3303	0.116*
H10C	−1.3821	0.2112	0.3459	0.116*
C11	−0.9309 (6)	0.2535 (4)	0.34049 (13)	0.0338 (9)
C12	−0.8603 (6)	0.3570 (4)	0.31824 (13)	0.0388 (10)
H12	−0.8704	0.4346	0.3317	0.047*
C13	−0.7751 (7)	0.3450 (5)	0.27617 (14)	0.0442 (10)
C14	−0.7607 (8)	0.2313 (5)	0.25529 (15)	0.0528 (13)
H14	−0.7037	0.2241	0.2269	0.063*
C15	−0.8316 (8)	0.1289 (5)	0.27677 (14)	0.0523 (13)
H15	−0.8234	0.0519	0.2628	0.063*
C16	−0.9167 (6)	0.1400 (4)	0.31989 (13)	0.0412 (10)
H16	−0.9634	0.0701	0.3344	0.049*
C17	−0.6939 (10)	0.5617 (5)	0.27368 (17)	0.0643 (15)
H17A	−0.8170	0.5840	0.2839	0.096*
H17B	−0.6501	0.6220	0.2521	0.096*
H17C	−0.6104	0.5590	0.2993	0.096*
C18	−0.5553 (6)	0.1854 (4)	0.09532 (14)	0.0357 (9)
C19	−0.3405 (5)	0.1845 (4)	0.09492 (14)	0.0348 (9)
H19	−0.2979	0.1022	0.1042	0.042*
C20	−0.2607 (5)	0.2792 (4)	0.12837 (13)	0.0311 (8)
H20	−0.3144	0.2636	0.1586	0.037*
C21	−0.0461 (6)	0.2685 (3)	0.13173 (12)	0.0304 (8)

	U11	U22	U33	U12	U13	U23
O1	0.102 (3)	0.054 (2)	0.0493 (19)	−0.015 (2)	0.036 (2)	−0.0117 (16)
O2	0.093 (3)	0.062 (2)	0.0337 (16)	−0.020 (2)	0.0192 (19)	−0.0047 (14)
O3	0.0267 (13)	0.0508 (18)	0.0499 (17)	−0.0006 (14)	−0.0032 (13)	0.0072 (15)
O4	0.0358 (17)	0.102 (3)	0.0504 (19)	−0.001 (2)	−0.0073 (16)	0.0149 (19)
O5	0.0355 (16)	0.071 (2)	0.0396 (16)	0.0106 (16)	0.0018 (14)	−0.0067 (15)
O6	0.0343 (16)	0.0337 (15)	0.0612 (19)	0.0056 (13)	0.0115 (15)	0.0052 (13)
O7	0.0328 (15)	0.0357 (16)	0.076 (2)	−0.0038 (14)	−0.0019 (17)	0.0016 (15)
O8	0.0268 (14)	0.0354 (15)	0.0550 (17)	0.0019 (12)	−0.0009 (13)	0.0041 (13)
O9	0.0393 (18)	0.059 (2)	0.0433 (19)	−0.0009 (16)	0.0073 (16)	−0.0042 (16)
O10	0.0456 (19)	0.0567 (19)	0.0392 (17)	0.0046 (18)	0.0032 (17)	−0.0048 (15)
N1	0.070 (3)	0.0334 (18)	0.0320 (18)	0.006 (2)	−0.007 (2)	−0.0040 (14)
C2	0.042 (2)	0.032 (2)	0.040 (2)	−0.0049 (19)	0.0031 (19)	0.0004 (17)
C3	0.034 (2)	0.0302 (19)	0.038 (2)	0.0035 (18)	0.0068 (19)	0.0033 (16)
C4	0.077 (3)	0.033 (2)	0.034 (2)	−0.005 (2)	0.024 (2)	−0.0071 (17)
C5A	0.055 (3)	0.078 (4)	0.039 (2)	−0.020 (3)	−0.007 (2)	−0.008 (2)
C6A	0.039 (3)	0.079 (4)	0.029 (3)	0.018 (3)	−0.008 (2)	0.004 (3)
C7A	0.074 (4)	0.061 (3)	0.073 (3)	0.007 (3)	−0.020 (3)	−0.002 (3)
C5B	0.055 (3)	0.078 (4)	0.039 (2)	−0.020 (3)	−0.007 (2)	−0.008 (2)
C6B	0.086 (18)	0.046 (9)	0.014 (8)	0.022 (10)	−0.020 (11)	−0.001 (8)
C7B	0.074 (4)	0.061 (3)	0.073 (3)	0.007 (3)	−0.020 (3)	−0.002 (3)
C8	0.147 (7)	0.049 (3)	0.050 (3)	0.009 (4)	0.039 (4)	0.014 (2)
C9	0.048 (3)	0.061 (3)	0.062 (3)	0.016 (3)	0.009 (3)	0.011 (2)
C10	0.050 (3)	0.104 (5)	0.077 (4)	0.020 (4)	−0.010 (3)	0.003 (4)
C11	0.030 (2)	0.042 (2)	0.0300 (18)	0.0037 (18)	−0.0032 (17)	0.0003 (16)
C12	0.046 (2)	0.043 (2)	0.0281 (19)	−0.003 (2)	−0.0044 (18)	−0.0038 (17)
C13	0.043 (2)	0.056 (3)	0.033 (2)	−0.005 (2)	−0.0041 (19)	0.0015 (19)
C14	0.059 (3)	0.068 (3)	0.032 (2)	0.000 (3)	0.006 (2)	−0.009 (2)
C15	0.068 (3)	0.051 (3)	0.038 (2)	0.000 (3)	0.002 (2)	−0.011 (2)
C16	0.048 (3)	0.039 (2)	0.036 (2)	0.006 (2)	0.0024 (19)	0.0006 (17)
C17	0.083 (4)	0.060 (3)	0.050 (3)	−0.017 (3)	0.003 (3)	0.004 (2)
C18	0.0300 (19)	0.037 (2)	0.040 (2)	0.0026 (18)	−0.004 (2)	−0.0023 (17)
C19	0.028 (2)	0.036 (2)	0.040 (2)	0.0058 (17)	−0.0012 (18)	0.0007 (17)
C20	0.0279 (19)	0.0302 (19)	0.0351 (19)	0.0021 (16)	0.0045 (17)	0.0018 (16)
C21	0.0273 (18)	0.033 (2)	0.0313 (18)	−0.0011 (17)	0.0036 (17)	0.0027 (15)

O1—C4	1.434 (5)	C6A—H6A	0.9700
O1—H1X	0.83 (2)	C6A—H6B	0.9700
O2—C13	1.380 (6)	C7A—H7A	0.9700
O2—C17	1.420 (6)	C7A—H7B	0.9700
O3—C18	1.289 (5)	C6B—H6B1	0.9700
O3—H3	0.8200	C6B—H6B2	0.9700
O4—C18	1.207 (5)	C8—H8A	0.9599
O5—C19	1.404 (5)	C8—H8B	0.9599
O5—H5	0.8200	C8—H8C	0.9599
O6—C20	1.403 (5)	C9—C10	1.482 (8)
O6—H6	0.8200	C9—H9A	0.9700
O7—C21	1.230 (5)	C9—H9B	0.9700
O8—C21	1.252 (5)	C10—H10A	0.9599
O9—H9X	0.83 (2)	C10—H10B	0.9599
O9—H9Y	0.83 (2)	C10—H10C	0.9599
O10—H10X	0.82 (2)	C11—C16	1.371 (6)
O10—H10Y	0.82 (2)	C11—C12	1.391 (6)
N1—C7A	1.447 (7)	C12—C13	1.383 (6)
N1—C2	1.496 (6)	C12—H12	0.9300
N1—C8	1.538 (7)	C13—C14	1.377 (7)
N1—H1	0.890 (19)	C14—C15	1.371 (7)
C2—C3	1.551 (5)	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.409 (6)
C2—H2B	0.9700	C15—H15	0.9300
C3—C11	1.526 (5)	C16—H16	0.9300
C3—C9	1.548 (7)	C17—H17A	0.9599
C3—C4	1.568 (6)	C17—H17B	0.9599
C4—C5A	1.528 (8)	C17—H17C	0.9599
C4—H4	0.9800	C18—C19	1.536 (6)
C5A—C6A	1.606 (8)	C19—C20	1.528 (6)
C5A—H5A	0.9700	C19—H19	0.9800
C5A—H5B	0.9700	C20—C21	1.541 (6)
C6A—C7A	1.446 (8)	C20—H20	0.9800
C4—O1—H1X	106 (6)	H8B—C8—H8C	109.5
C13—O2—C17	119.2 (4)	C10—C9—C3	116.2 (5)
C18—O3—H3	109.5	C10—C9—H9A	108.2
C19—O5—H5	109.5	C3—C9—H9A	108.2
C20—O6—H6	109.5	C10—C9—H9B	108.2
H9X—O9—H9Y	101 (6)	C3—C9—H9B	108.2
H10X—O10—H10Y	89 (5)	H9A—C9—H9B	107.4
C7A—N1—C2	119.1 (4)	C9—C10—H10A	109.5
C7A—N1—C8	105.4 (4)	C9—C10—H10B	109.5
C2—N1—C8	106.5 (4)	H10A—C10—H10B	109.5
C7A—N1—H1	115 (3)	C9—C10—H10C	109.5
C2—N1—H1	107 (3)	H10A—C10—H10C	109.5
C8—N1—H1	103 (3)	H10B—C10—H10C	109.5
N1—C2—C3	121.0 (4)	C16—C11—C12	119.1 (4)
N1—C2—H2A	107.1	C16—C11—C3	123.0 (4)
C3—C2—H2A	107.1	C12—C11—C3	117.7 (3)
N1—C2—H2B	107.1	C13—C12—C11	120.2 (4)
C3—C2—H2B	107.1	C13—C12—H12	119.9
H2A—C2—H2B	106.8	C11—C12—H12	119.9
C11—C3—C9	107.8 (3)	C14—C13—O2	115.9 (4)
C11—C3—C2	115.8 (3)	C14—C13—C12	121.0 (4)
C9—C3—C2	105.1 (4)	O2—C13—C12	123.1 (4)
C11—C3—C4	111.2 (3)	C15—C14—C13	119.3 (4)
C9—C3—C4	105.9 (4)	C15—C14—H14	120.4
C2—C3—C4	110.3 (3)	C13—C14—H14	120.4
O1—C4—C5A	109.8 (4)	C14—C15—C16	120.2 (4)
O1—C4—C3	108.7 (4)	C14—C15—H15	119.9
C5A—C4—C3	115.5 (4)	C16—C15—H15	119.9
O1—C4—H4	107.5	C11—C16—C15	120.3 (4)
C5A—C4—H4	107.5	C11—C16—H16	119.9
C3—C4—H4	107.5	C15—C16—H16	119.9
C4—C5A—C6A	115.1 (4)	O2—C17—H17A	109.5
C4—C5A—H5A	108.5	O2—C17—H17B	109.5
C6A—C5A—H5A	108.5	H17A—C17—H17B	109.5
C4—C5A—H5B	108.5	O2—C17—H17C	109.5
C6A—C5A—H5B	108.5	H17A—C17—H17C	109.5
H5A—C5A—H5B	107.5	H17B—C17—H17C	109.5
C7A—C6A—C5A	116.5 (5)	O4—C18—O3	126.3 (4)
C7A—C6A—H6A	108.2	O4—C18—C19	119.7 (4)
C5A—C6A—H6A	108.2	O3—C18—C19	114.0 (4)
C7A—C6A—H6B	108.2	O5—C19—C20	111.0 (3)
C5A—C6A—H6B	108.2	O5—C19—C18	109.6 (3)
H6A—C6A—H6B	107.3	C20—C19—C18	111.4 (3)
C6A—C7A—N1	111.2 (5)	O5—C19—H19	108.3
C6A—C7A—H7A	109.4	C20—C19—H19	108.3
N1—C7A—H7A	109.4	C18—C19—H19	108.3
C6A—C7A—H7B	109.4	O6—C20—C19	110.5 (3)
N1—C7A—H7B	109.4	O6—C20—C21	109.3 (3)
H7A—C7A—H7B	108.0	C19—C20—C21	111.2 (3)
H6B1—C6B—H6B2	105.5	O6—C20—H20	108.6
N1—C8—H8A	109.5	C19—C20—H20	108.6
N1—C8—H8B	109.5	C21—C20—H20	108.6
H8A—C8—H8B	109.5	O7—C21—O8	125.7 (4)
N1—C8—H8C	109.5	O7—C21—C20	117.3 (4)
H8A—C8—H8C	109.5	O8—C21—C20	117.0 (3)
C7A—N1—C2—C3	50.1 (6)	C4—C3—C11—C12	−48.4 (5)
C8—N1—C2—C3	168.8 (4)	C16—C11—C12—C13	−0.8 (6)
N1—C2—C3—C11	62.8 (5)	C3—C11—C12—C13	−175.4 (4)
N1—C2—C3—C9	−178.4 (4)	C17—O2—C13—C14	−174.2 (5)
N1—C2—C3—C4	−64.6 (5)	C17—O2—C13—C12	5.9 (8)
C11—C3—C4—O1	−172.6 (4)	C11—C12—C13—C14	0.9 (7)
C9—C3—C4—O1	70.6 (5)	C11—C12—C13—O2	−179.2 (4)
C2—C3—C4—O1	−42.7 (5)	O2—C13—C14—C15	179.8 (5)
C11—C3—C4—C5A	−48.7 (5)	C12—C13—C14—C15	−0.3 (7)
C9—C3—C4—C5A	−165.5 (4)	C13—C14—C15—C16	−0.5 (8)
C2—C3—C4—C5A	81.2 (4)	C12—C11—C16—C15	0.0 (7)
O1—C4—C5A—C6A	83.7 (5)	C3—C11—C16—C15	174.4 (4)
C3—C4—C5A—C6A	−39.7 (5)	C14—C15—C16—C11	0.6 (7)
C4—C5A—C6A—C7A	−41.9 (6)	O4—C18—C19—O5	−6.3 (6)
C5A—C6A—C7A—N1	88.8 (6)	O3—C18—C19—O5	174.0 (3)
C2—N1—C7A—C6A	−68.9 (6)	O4—C18—C19—C20	116.9 (5)
C8—N1—C7A—C6A	171.8 (5)	O3—C18—C19—C20	−62.9 (5)
C11—C3—C9—C10	50.3 (6)	O5—C19—C20—O6	57.8 (4)
C2—C3—C9—C10	−73.7 (5)	C18—C19—C20—O6	−64.6 (4)
C4—C3—C9—C10	169.4 (5)	O5—C19—C20—C21	−63.7 (4)
C9—C3—C11—C16	−107.3 (5)	C18—C19—C20—C21	173.9 (3)
C2—C3—C11—C16	10.1 (6)	O6—C20—C21—O7	13.9 (5)
C4—C3—C11—C16	137.1 (4)	C19—C20—C21—O7	136.2 (4)
C9—C3—C11—C12	67.2 (5)	O6—C20—C21—O8	−168.1 (3)
C2—C3—C11—C12	−175.4 (4)	C19—C20—C21—O8	−45.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4	0.82	2.15	2.623 (5)	116
O6—H6···O9	0.82	1.91	2.641 (5)	149
O9—H9X···O2	0.83 (2)	2.00 (2)	2.823 (5)	171 (6)
O10—H10X···O5	0.82 (2)	1.98 (2)	2.790 (5)	173 (6)
C7A—H7A···O1	0.97	2.56	3.149 (8)	119
C6B—H6B1···O1	0.97	1.91	2.46 (3)	113
O9—H9Y···O7i	0.83 (2)	1.85 (2)	2.680 (5)	171 (7)
O3—H3···O8i	0.82	1.73	2.516 (4)	160
O5—H5···O10ii	0.82	2.27	2.983 (5)	145
O10—H10Y···O4iii	0.82 (2)	2.02 (4)	2.739 (5)	145 (6)
C16—H16···O7iv	0.93	2.50	3.417 (6)	171
C7B—H7B1···O6iv	0.97	2.51	3.176 (7)	126
C6B—H6B2···O1v	0.97	2.39	3.056 (17)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O4	0.82	2.15	2.623 (5)	116
O6—H6⋯O9	0.82	1.91	2.641 (5)	149
O9—H9X⋯O2	0.83 (2)	2.00 (2)	2.823 (5)	171 (6)
O10—H10X⋯O5	0.82 (2)	1.98 (2)	2.790 (5)	173 (6)
C7A—H7A⋯O1	0.97	2.56	3.149 (8)	119
C6B—H6B1⋯O1	0.97	1.91	2.46 (3)	113
O9—H9Y⋯O7i	0.83 (2)	1.85 (2)	2.680 (5)	171 (7)
O3—H3⋯O8i	0.82	1.73	2.516 (4)	160
O5—H5⋯O10ii	0.82	2.27	2.983 (5)	145
O10—H10Y⋯O4iii	0.82 (2)	2.02 (4)	2.739 (5)	145 (6)
C16—H16⋯O7iv	0.93	2.50	3.417 (6)	171
C7B—H7B1⋯O6iv	0.97	2.51	3.176 (7)	126
C6B—H6B2⋯O1v	0.97	2.39	3.056 (17)	125

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