Desvenlafaxinium chloranilate ethyl acetate solvate.

In the cation of the title compound, C16H26NO2 (+)·C6HCl2O4 (-)·C4H8O2, the 1-hy-droxy-cyclo-hexyl ring adopts a slightly distorted chair conformation. The dihedral angle between the mean planes of the 1-hy-droxy-cyclo-hexyl and 4-hy-droxy-phenyl rings is 84.0 (8)°. In the anion, the hydroxyl H atom is twisted slightly out of the ring plane with a C-C-O-H torsion angle of -171.9°. Disorder was modeled for the methyl group of the acetate group in the solvate with an occupancy ratio of 0.583 (15): 0.417 (15). In the crystal, O-H⋯O hydrogen bonds are observed between cations and between cations and anions, while bifuricated N-H⋯(O,O) cation-anion hydrogen bonds are also present, forming chains along [010] and [100]. In addition weak cation-anion and cation-solvate C-H⋯O inter-actions occur.

Related literature

For the pharmacological importance of Desvenlafaxine {systematic name: 4-[2-di­methyl­amino-1-(1-hy­droxy­cyclo­hex­yl)eth­yl]phenol}, see: Deecher et al. (2006 ▶). For related structures, see: Dayananda et al. (2012 ▶); Duggirala et al. (2009 ▶); Hadfield et al. (2004 ▶); Mungkornasawakul et al. (2009 ▶); Sivalakshmidevi et al. (2002 ▶); Sun et al. (2006 ▶); Tessler & Goldberg (2004 ▶); Vega et al. (2000 ▶); Venu et al. (2008 ▶); Zhang et al. (2006 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H26NO2 +·C6HCl2O4 −·C4H8O2

M = 560.45

Monoclinic,

a = 11.1738 (2) Å

b = 9.39846 (16) Å

c = 13.6046 (2) Å

β = 105.109 (2)°

V = 1379.33 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 123 K

0.44 × 0.29 × 0.12 mm

Data collection

Agilent Xcalibur, Ruby, Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.991, T max = 1.000

16094 measured reflections

8667 independent reflections

7926 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.158

S = 1.05

8667 reflections

351 parameters

16 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.16 e Å−3

Δρmin = −0.75 e Å−3

Absolute structure: Flack (1983 ▶), 3959 Friedel pairs

Absolute structure parameter: 0.01 (5)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); 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 datablock(s) I. DOI: 10.1107/S1600536813025312/hg5346sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025312/hg5346Isup2.hkl

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

C16H26NO2+·C6HCl2O4−·C4H8O2	F(000) = 592
Mr = 560.45	Dx = 1.349 Mg m−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P -2yac	Cell parameters from 8855 reflections
a = 11.1738 (2) Å	θ = 3.1–32.6°
b = 9.39846 (16) Å	µ = 0.28 mm−1
c = 13.6046 (2) Å	T = 123 K
β = 105.109 (2)°	Prism, black
V = 1379.33 (4) Å3	0.44 × 0.29 × 0.12 mm
Z = 2

Agilent Xcalibur, Ruby, Gemini diffractometer	8667 independent reflections
Radiation source: Enhance (Mo) X-ray Source	7926 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 10.5081 pixels mm-1	θmax = 32.7°, θmin = 3.1°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −12→13
Tmin = 0.991, Tmax = 1.000	l = −19→20
16094 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)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.158	w = 1/[σ2(Fo2) + (0.0965P)2 + 0.5142P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.006
8667 reflections	Δρmax = 1.16 e Å−3
351 parameters	Δρmin = −0.75 e Å−3
16 restraints	Absolute structure: Flack (1983), ???? Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (5)

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	Occ. (<1)
O1	0.47746 (18)	1.43604 (18)	0.31751 (16)	0.0265 (4)
H1	0.5338	1.4903	0.3093	0.040*
O2	0.62810 (17)	0.62374 (17)	0.26371 (15)	0.0223 (3)
H2	0.7043	0.6213	0.2928	0.033*
N1	0.73387 (19)	0.7670 (2)	0.52239 (15)	0.0185 (3)
H1N	0.792 (3)	0.737 (3)	0.493 (2)	0.012 (6)*
C1	0.5942 (2)	1.0116 (2)	0.33682 (17)	0.0178 (4)
C2	0.4800 (2)	1.0512 (2)	0.35322 (18)	0.0197 (4)
H2A	0.4279	0.9801	0.3696	0.024*
C3	0.4413 (2)	1.1925 (2)	0.34606 (19)	0.0214 (4)
H3A	0.3633	1.2171	0.3570	0.026*
C4	0.5178 (2)	1.2981 (2)	0.32262 (17)	0.0192 (4)
C5	0.6322 (2)	1.2609 (2)	0.3069 (2)	0.0235 (4)
H5A	0.6847	1.3320	0.2911	0.028*
C6	0.6692 (2)	1.1186 (2)	0.31463 (19)	0.0216 (4)
H6A	0.7476	1.0942	0.3045	0.026*
C7	0.6381 (2)	0.8573 (2)	0.34508 (17)	0.0171 (3)
H7A	0.7302	0.8614	0.3567	0.020*
C8	0.6151 (2)	0.7795 (2)	0.43892 (17)	0.0194 (4)
H8A	0.5530	0.8329	0.4646	0.023*
H8B	0.5815	0.6834	0.4187	0.023*
C9	0.7782 (3)	0.9077 (3)	0.5675 (2)	0.0312 (5)
H9A	0.8571	0.8957	0.6191	0.047*
H9B	0.7166	0.9485	0.5993	0.047*
H9C	0.7899	0.9717	0.5139	0.047*
C10	0.7170 (3)	0.6668 (3)	0.6020 (2)	0.0311 (5)
H10A	0.7952	0.6574	0.6548	0.047*
H10B	0.6919	0.5735	0.5713	0.047*
H10C	0.6527	0.7033	0.6325	0.047*
C11	0.5888 (2)	0.7699 (2)	0.24491 (18)	0.0195 (4)
C12	0.4476 (2)	0.7658 (3)	0.20590 (19)	0.0229 (4)
H12A	0.4154	0.8644	0.1965	0.027*
H12B	0.4125	0.7193	0.2574	0.027*
C13	0.4050 (3)	0.6854 (3)	0.1051 (2)	0.0345 (6)
H13A	0.4278	0.5838	0.1163	0.041*
H13B	0.3136	0.6914	0.0802	0.041*
C14	0.4635 (3)	0.7462 (4)	0.0246 (2)	0.0412 (7)
H14A	0.4379	0.6884	−0.0382	0.049*
H14B	0.4336	0.8446	0.0079	0.049*
C15	0.6038 (3)	0.7465 (3)	0.0623 (2)	0.0356 (6)
H15A	0.6397	0.7905	0.0103	0.043*
H15B	0.6344	0.6474	0.0732	0.043*
C16	0.6452 (3)	0.8295 (3)	0.1618 (2)	0.0271 (5)
H16A	0.6205	0.9303	0.1491	0.033*
H16B	0.7368	0.8260	0.1862	0.033*
Cl1	0.92007 (8)	0.40363 (7)	0.25545 (6)	0.02721 (13)
Cl2	1.28410 (9)	0.82486 (7)	0.55657 (6)	0.03231 (14)
O1A	1.19739 (19)	0.4153 (2)	0.31197 (16)	0.0300 (4)
O2A	1.34999 (18)	0.5944 (2)	0.42885 (16)	0.0284 (4)
H2A1	1.3584	0.5362	0.3842	0.043*
O3A	1.0108 (2)	0.7925 (3)	0.52380 (19)	0.0397 (5)
O4A	0.85246 (17)	0.6185 (2)	0.39869 (15)	0.0254 (3)
C1A	1.0159 (2)	0.5140 (2)	0.34403 (17)	0.0197 (4)
C2A	1.1458 (2)	0.5020 (3)	0.35560 (18)	0.0205 (4)
C3A	1.2306 (2)	0.6058 (2)	0.42625 (18)	0.0212 (4)
C4A	1.1866 (2)	0.7035 (2)	0.48058 (19)	0.0221 (4)
C5A	1.0544 (2)	0.7100 (3)	0.47477 (19)	0.0233 (4)
C6A	0.9653 (2)	0.6072 (2)	0.40123 (17)	0.0186 (4)
O1S	0.5308 (4)	0.9814 (5)	0.6374 (3)	0.0818 (12)
O2S	0.4947 (3)	1.1593 (3)	0.7334 (2)	0.0530 (7)
C1S	0.5324 (4)	1.0314 (5)	0.7221 (4)	0.0620 (11)
C2SA	0.5724 (11)	0.9564 (8)	0.8264 (4)	0.0518 (16)	0.583 (15)
H2S1	0.5631	0.8533	0.8167	0.078*	0.583 (15)
H2S2	0.5202	0.9892	0.8697	0.078*	0.583 (15)
H2S3	0.6593	0.9791	0.8591	0.078*	0.583 (15)
C2SB	0.6165 (11)	0.9595 (13)	0.8173 (7)	0.0518 (16)	0.417 (15)
H2S4	0.6065	0.8560	0.8112	0.078*	0.417 (15)
H2S5	0.5932	0.9922	0.8781	0.078*	0.417 (15)
H2S6	0.7031	0.9845	0.8229	0.078*	0.417 (15)
C3S	0.4586 (5)	1.2355 (5)	0.6368 (3)	0.0573 (10)
H3SA	0.4192	1.1665	0.5831	0.069*
H3SB	0.3946	1.3063	0.6412	0.069*
C4S	0.5560 (5)	1.3091 (5)	0.6040 (3)	0.0588 (11)
H4SA	0.5193	1.3843	0.5556	0.088*
H4SB	0.5997	1.2412	0.5710	0.088*
H4SC	0.6147	1.3512	0.6632	0.088*

	U11	U22	U33	U12	U13	U23
O1	0.0254 (8)	0.0144 (7)	0.0431 (10)	0.0010 (6)	0.0148 (8)	0.0025 (7)
O2	0.0191 (7)	0.0141 (7)	0.0317 (8)	0.0010 (5)	0.0029 (6)	0.0004 (6)
N1	0.0200 (8)	0.0184 (8)	0.0176 (7)	0.0013 (6)	0.0055 (7)	−0.0005 (6)
C1	0.0201 (9)	0.0148 (8)	0.0189 (9)	0.0006 (7)	0.0057 (7)	0.0016 (7)
C2	0.0202 (9)	0.0156 (9)	0.0251 (10)	−0.0014 (7)	0.0089 (8)	0.0022 (8)
C3	0.0198 (9)	0.0175 (9)	0.0283 (11)	−0.0009 (7)	0.0087 (9)	−0.0017 (8)
C4	0.0223 (9)	0.0150 (9)	0.0203 (9)	−0.0010 (7)	0.0058 (8)	0.0008 (7)
C5	0.0232 (10)	0.0151 (9)	0.0345 (12)	−0.0018 (7)	0.0117 (9)	0.0029 (8)
C6	0.0192 (9)	0.0165 (9)	0.0309 (11)	0.0012 (7)	0.0098 (8)	0.0030 (8)
C7	0.0173 (8)	0.0147 (8)	0.0199 (9)	−0.0005 (6)	0.0061 (7)	0.0018 (7)
C8	0.0180 (9)	0.0186 (9)	0.0216 (9)	−0.0002 (7)	0.0052 (8)	0.0042 (7)
C9	0.0332 (12)	0.0308 (12)	0.0292 (12)	−0.0045 (10)	0.0076 (10)	−0.0100 (10)
C10	0.0335 (12)	0.0331 (13)	0.0258 (11)	0.0007 (10)	0.0063 (10)	0.0117 (10)
C11	0.0211 (9)	0.0138 (8)	0.0235 (10)	0.0017 (7)	0.0056 (8)	0.0011 (7)
C12	0.0200 (9)	0.0204 (10)	0.0263 (10)	0.0043 (8)	0.0026 (8)	0.0004 (8)
C13	0.0324 (13)	0.0308 (13)	0.0324 (13)	0.0056 (10)	−0.0056 (11)	−0.0094 (10)
C14	0.0528 (18)	0.0419 (16)	0.0235 (12)	0.0184 (14)	0.0002 (12)	−0.0048 (11)
C15	0.0486 (17)	0.0328 (14)	0.0275 (12)	0.0094 (11)	0.0135 (12)	−0.0048 (10)
C16	0.0362 (13)	0.0239 (11)	0.0250 (10)	−0.0016 (9)	0.0149 (10)	−0.0010 (9)
Cl1	0.0233 (2)	0.0315 (3)	0.0264 (2)	−0.0068 (2)	0.0058 (2)	−0.0084 (2)
Cl2	0.0268 (3)	0.0285 (3)	0.0361 (3)	−0.0017 (2)	−0.0016 (2)	−0.0107 (3)
O1A	0.0235 (8)	0.0338 (10)	0.0336 (10)	0.0004 (7)	0.0091 (8)	−0.0118 (8)
O2A	0.0199 (8)	0.0311 (9)	0.0350 (10)	−0.0031 (6)	0.0087 (7)	−0.0084 (8)
O3A	0.0288 (10)	0.0425 (12)	0.0469 (13)	0.0034 (8)	0.0086 (9)	−0.0233 (10)
O4A	0.0179 (7)	0.0300 (9)	0.0278 (8)	0.0035 (6)	0.0050 (6)	−0.0038 (7)
C1A	0.0184 (9)	0.0204 (9)	0.0202 (9)	0.0000 (7)	0.0046 (8)	−0.0005 (7)
C2A	0.0186 (9)	0.0215 (10)	0.0219 (10)	−0.0022 (7)	0.0061 (8)	−0.0007 (8)
C3A	0.0199 (10)	0.0214 (10)	0.0225 (10)	0.0001 (7)	0.0059 (8)	0.0010 (8)
C4A	0.0224 (10)	0.0192 (9)	0.0221 (10)	−0.0005 (8)	0.0013 (8)	−0.0037 (8)
C5A	0.0204 (10)	0.0240 (10)	0.0234 (10)	0.0037 (8)	0.0019 (8)	−0.0023 (8)
C6A	0.0178 (9)	0.0191 (9)	0.0185 (9)	0.0029 (7)	0.0039 (7)	0.0015 (7)
O1S	0.064 (2)	0.100 (3)	0.090 (2)	−0.025 (2)	0.0364 (19)	−0.057 (2)
O2S	0.0581 (16)	0.0435 (14)	0.0621 (17)	−0.0014 (12)	0.0242 (13)	−0.0122 (13)
C1S	0.0401 (19)	0.049 (2)	0.091 (3)	0.0023 (16)	0.007 (2)	−0.009 (2)
C2SA	0.090 (5)	0.040 (2)	0.036 (2)	−0.024 (3)	0.036 (3)	−0.0036 (17)
C2SB	0.090 (5)	0.040 (2)	0.036 (2)	−0.024 (3)	0.036 (3)	−0.0036 (17)
C3S	0.061 (2)	0.067 (3)	0.0426 (19)	−0.022 (2)	0.0122 (18)	−0.0046 (18)
C4S	0.081 (3)	0.047 (2)	0.047 (2)	−0.021 (2)	0.014 (2)	−0.0082 (16)

O1—C4	1.368 (3)	C14—C15	1.517 (5)
O1—H1	0.8400	C14—H14A	0.9900
O2—C11	1.444 (3)	C14—H14B	0.9900
O2—H2	0.8400	C15—C16	1.526 (4)
N1—C10	1.484 (3)	C15—H15A	0.9900
N1—C9	1.487 (3)	C15—H15B	0.9900
N1—C8	1.510 (3)	C16—H16A	0.9900
N1—H1N	0.89 (3)	C16—H16B	0.9900
C1—C6	1.392 (3)	Cl1—C1A	1.733 (2)
C1—C2	1.402 (3)	Cl2—C4A	1.723 (2)
C1—C7	1.526 (3)	O1A—C2A	1.236 (3)
C2—C3	1.392 (3)	O2A—C3A	1.330 (3)
C2—H2A	0.9500	O2A—H2A1	0.8400
C3—C4	1.401 (3)	O3A—C5A	1.205 (3)
C3—H3A	0.9500	O4A—C6A	1.256 (3)
C4—C5	1.395 (3)	C1A—C6A	1.386 (3)
C5—C6	1.395 (3)	C1A—C2A	1.423 (3)
C5—H5A	0.9500	C2A—C3A	1.516 (3)
C6—H6A	0.9500	C3A—C4A	1.348 (3)
C7—C8	1.550 (3)	C4A—C5A	1.460 (3)
C7—C11	1.563 (3)	C5A—C6A	1.551 (3)
C7—H7A	1.0000	O1S—C1S	1.240 (6)
C8—H8A	0.9900	O2S—C1S	1.295 (5)
C8—H8B	0.9900	O2S—C3S	1.459 (6)
C9—H9A	0.9800	C1S—C2SA	1.543 (7)
C9—H9B	0.9800	C1S—C2SB	1.544 (7)
C9—H9C	0.9800	C2SA—H2S1	0.9800
C10—H10A	0.9800	C2SA—H2S2	0.9800
C10—H10B	0.9800	C2SA—H2S3	0.9800
C10—H10C	0.9800	C2SB—H2S4	0.9800
C11—C12	1.528 (3)	C2SB—H2S5	0.9800
C11—C16	1.536 (3)	C2SB—H2S6	0.9800
C12—C13	1.530 (4)	C3S—C4S	1.455 (6)
C12—H12A	0.9900	C3S—H3SA	0.9900
C12—H12B	0.9900	C3S—H3SB	0.9900
C13—C14	1.525 (5)	C4S—H4SA	0.9800
C13—H13A	0.9900	C4S—H4SB	0.9800
C13—H13B	0.9900	C4S—H4SC	0.9800
C4—O1—H1	109.5	H13A—C13—H13B	108.0
C11—O2—H2	109.5	C15—C14—C13	110.9 (2)
C10—N1—C9	110.8 (2)	C15—C14—H14A	109.5
C10—N1—C8	110.14 (19)	C13—C14—H14A	109.5
C9—N1—C8	112.0 (2)	C15—C14—H14B	109.5
C10—N1—H1N	111.7 (19)	C13—C14—H14B	109.5
C9—N1—H1N	105.4 (19)	H14A—C14—H14B	108.0
C8—N1—H1N	107 (2)	C14—C15—C16	110.4 (2)
C6—C1—C2	117.82 (19)	C14—C15—H15A	109.6
C6—C1—C7	120.20 (18)	C16—C15—H15A	109.6
C2—C1—C7	121.96 (18)	C14—C15—H15B	109.6
C3—C2—C1	121.46 (19)	C16—C15—H15B	109.6
C3—C2—H2A	119.3	H15A—C15—H15B	108.1
C1—C2—H2A	119.3	C15—C16—C11	112.3 (2)
C2—C3—C4	119.7 (2)	C15—C16—H16A	109.1
C2—C3—H3A	120.2	C11—C16—H16A	109.1
C4—C3—H3A	120.2	C15—C16—H16B	109.1
O1—C4—C5	122.22 (19)	C11—C16—H16B	109.1
O1—C4—C3	118.08 (19)	H16A—C16—H16B	107.9
C5—C4—C3	119.7 (2)	C3A—O2A—H2A1	109.5
C4—C5—C6	119.63 (19)	C6A—C1A—C2A	122.8 (2)
C4—C5—H5A	120.2	C6A—C1A—Cl1	120.00 (16)
C6—C5—H5A	120.2	C2A—C1A—Cl1	117.20 (17)
C1—C6—C5	121.7 (2)	O1A—C2A—C1A	126.1 (2)
C1—C6—H6A	119.1	O1A—C2A—C3A	115.9 (2)
C5—C6—H6A	119.1	C1A—C2A—C3A	118.0 (2)
C1—C7—C8	112.93 (17)	O2A—C3A—C4A	123.1 (2)
C1—C7—C11	113.69 (18)	O2A—C3A—C2A	114.93 (19)
C8—C7—C11	111.97 (17)	C4A—C3A—C2A	121.9 (2)
C1—C7—H7A	105.8	C3A—C4A—C5A	120.5 (2)
C8—C7—H7A	105.8	C3A—C4A—Cl2	121.06 (18)
C11—C7—H7A	105.8	C5A—C4A—Cl2	118.47 (17)
N1—C8—C7	110.75 (17)	O3A—C5A—C4A	123.1 (2)
N1—C8—H8A	109.5	O3A—C5A—C6A	118.3 (2)
C7—C8—H8A	109.5	C4A—C5A—C6A	118.60 (19)
N1—C8—H8B	109.5	O4A—C6A—C1A	126.2 (2)
C7—C8—H8B	109.5	O4A—C6A—C5A	115.83 (19)
H8A—C8—H8B	108.1	C1A—C6A—C5A	117.92 (19)
N1—C9—H9A	109.5	C1S—O2S—C3S	111.7 (4)
N1—C9—H9B	109.5	O1S—C1S—O2S	122.4 (5)
H9A—C9—H9B	109.5	O1S—C1S—C2SA	127.7 (5)
N1—C9—H9C	109.5	O2S—C1S—C2SA	109.8 (5)
H9A—C9—H9C	109.5	O1S—C1S—C2SB	118.1 (6)
H9B—C9—H9C	109.5	O2S—C1S—C2SB	116.9 (6)
N1—C10—H10A	109.5	C2SA—C1S—C2SB	20.1 (4)
N1—C10—H10B	109.5	C1S—C2SA—H2S1	109.5
H10A—C10—H10B	109.5	C1S—C2SA—H2S2	109.5
N1—C10—H10C	109.5	C1S—C2SA—H2S3	109.5
H10A—C10—H10C	109.5	C1S—C2SB—H2S4	109.5
H10B—C10—H10C	109.5	C1S—C2SB—H2S5	109.5
O2—C11—C12	106.03 (18)	H2S4—C2SB—H2S5	109.5
O2—C11—C16	108.25 (18)	C1S—C2SB—H2S6	109.5
C12—C11—C16	109.8 (2)	H2S4—C2SB—H2S6	109.5
O2—C11—C7	108.88 (18)	H2S5—C2SB—H2S6	109.5
C12—C11—C7	114.40 (17)	C4S—C3S—O2S	117.2 (4)
C16—C11—C7	109.33 (18)	C4S—C3S—H3SA	108.0
C11—C12—C13	112.1 (2)	O2S—C3S—H3SA	108.0
C11—C12—H12A	109.2	C4S—C3S—H3SB	108.0
C13—C12—H12A	109.2	O2S—C3S—H3SB	108.0
C11—C12—H12B	109.2	H3SA—C3S—H3SB	107.2
C13—C12—H12B	109.2	C3S—C4S—H4SA	109.5
H12A—C12—H12B	107.9	C3S—C4S—H4SB	109.5
C14—C13—C12	111.5 (2)	H4SA—C4S—H4SB	109.5
C14—C13—H13A	109.3	C3S—C4S—H4SC	109.5
C12—C13—H13A	109.3	H4SA—C4S—H4SC	109.5
C14—C13—H13B	109.3	H4SB—C4S—H4SC	109.5
C12—C13—H13B	109.3
C6—C1—C2—C3	1.0 (3)	O2—C11—C16—C15	60.0 (3)
C7—C1—C2—C3	179.6 (2)	C12—C11—C16—C15	−55.3 (3)
C1—C2—C3—C4	−0.4 (4)	C7—C11—C16—C15	178.5 (2)
C2—C3—C4—O1	−179.2 (2)	C6A—C1A—C2A—O1A	175.1 (2)
C2—C3—C4—C5	−0.2 (3)	Cl1—C1A—C2A—O1A	−3.8 (3)
O1—C4—C5—C6	179.0 (2)	C6A—C1A—C2A—C3A	−6.0 (3)
C3—C4—C5—C6	0.1 (4)	Cl1—C1A—C2A—C3A	175.06 (16)
C2—C1—C6—C5	−1.1 (4)	O1A—C2A—C3A—O2A	2.9 (3)
C7—C1—C6—C5	−179.7 (2)	C1A—C2A—C3A—O2A	−176.1 (2)
C4—C5—C6—C1	0.6 (4)	O1A—C2A—C3A—C4A	−178.2 (2)
C6—C1—C7—C8	134.9 (2)	C1A—C2A—C3A—C4A	2.8 (3)
C2—C1—C7—C8	−43.6 (3)	O2A—C3A—C4A—C5A	−179.7 (2)
C6—C1—C7—C11	−96.1 (2)	C2A—C3A—C4A—C5A	1.5 (4)
C2—C1—C7—C11	85.4 (2)	O2A—C3A—C4A—Cl2	1.4 (3)
C10—N1—C8—C7	−167.94 (19)	C2A—C3A—C4A—Cl2	−177.43 (18)
C9—N1—C8—C7	68.3 (2)	C3A—C4A—C5A—O3A	177.9 (3)
C1—C7—C8—N1	−103.0 (2)	Cl2—C4A—C5A—O3A	−3.1 (4)
C11—C7—C8—N1	127.10 (19)	C3A—C4A—C5A—C6A	−2.8 (3)
C1—C7—C11—O2	−175.68 (16)	Cl2—C4A—C5A—C6A	176.18 (17)
C8—C7—C11—O2	−46.2 (2)	C2A—C1A—C6A—O4A	−176.3 (2)
C1—C7—C11—C12	−57.3 (2)	Cl1—C1A—C6A—O4A	2.6 (3)
C8—C7—C11—C12	72.2 (2)	C2A—C1A—C6A—C5A	4.7 (3)
C1—C7—C11—C16	66.2 (2)	Cl1—C1A—C6A—C5A	−176.40 (16)
C8—C7—C11—C16	−164.28 (18)	O3A—C5A—C6A—O4A	0.0 (4)
O2—C11—C12—C13	−62.9 (3)	C4A—C5A—C6A—O4A	−179.4 (2)
C16—C11—C12—C13	53.8 (3)	O3A—C5A—C6A—C1A	179.1 (2)
C7—C11—C12—C13	177.1 (2)	C4A—C5A—C6A—C1A	−0.3 (3)
C11—C12—C13—C14	−54.9 (3)	C3S—O2S—C1S—O1S	−3.2 (6)
C12—C13—C14—C15	55.8 (3)	C3S—O2S—C1S—C2SA	178.6 (5)
C13—C14—C15—C16	−56.6 (3)	C3S—O2S—C1S—C2SB	158.1 (7)
C14—C15—C16—C11	57.2 (3)	C1S—O2S—C3S—C4S	−86.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	1.85	2.669 (2)	166
O2—H2···O4A	0.84	1.89	2.694 (3)	160
N1—H1N···O4A	0.89 (3)	1.95 (3)	2.775 (3)	153 (3)
N1—H1N···O3A	0.89 (3)	2.43 (3)	3.099 (3)	132 (2)
O2A—H2A1···O1ii	0.84	2.03	2.768 (3)	147
C3—H3A···O1Aiii	0.95	2.59	3.371 (3)	140
C9—H9B···O1S	0.98	2.29	3.224 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.84	1.85	2.669 (2)	166
O2—H2⋯O4A	0.84	1.89	2.694 (3)	160
N1—H1N⋯O4A	0.89 (3)	1.95 (3)	2.775 (3)	153 (3)
N1—H1N⋯O3A	0.89 (3)	2.43 (3)	3.099 (3)	132 (2)
O2A—H2A1⋯O1ii	0.84	2.03	2.768 (3)	147
C3—H3A⋯O1A iii	0.95	2.59	3.371 (3)	140
C9—H9B⋯O1S	0.98	2.29	3.224 (4)	159

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