(9S,13R,14S)-7,8-Didehydro-4-(4-fluoro-benz-yloxy)-3,7-dimeth-oxy-17-methyl-morphinan-6-one sesquihydrate.

In the title sinomenine derivative, C(26)H(28)FNO(4)·1.5H(2)O, the dihedral angle between the two aromatic rings is 55.32 (6)°. The N-containing ring has an approximate chair conformation, while other two rings have approximate envelope and half-chair conformations. One water mol-ecule is located on a twofold symmetry axis. In the crystal, the water mol-ecules form O-H⋯O and O-H⋯N hydrogen bonds, bridging symmetry-related main mol-ecules.

Related literature

For background to the biological activity of sinomenine derivatives and other related compounds, see: Liu et al. (1994 ▶, 1996 ▶, 1997 ▶); Mark et al. (2003 ▶); Ye et al. (2004 ▶). For the synthesis of the title compound, see: Mitsunobu (1981 ▶). For related structures, see: Li et al. (2009 ▶); Batterham et al. (1965 ▶); Zheng & Jiang (2010 ▶); Zheng et al. (2011 ▶).

Experimental

Crystal data

C26H28FNO4·1.5H2O

M = 464.52

Monoclinic,

a = 18.0155 (3) Å

b = 7.6776 (1) Å

c = 18.1506 (4) Å

β = 109.324 (1)°

V = 2369.08 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.79 mm−1

T = 133 K

0.25 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.826, T max = 0.925

7232 measured reflections

3415 independent reflections

3402 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.081

S = 1.04

3415 reflections

312 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1359 Friedel pairs

Flack parameter: 0.05 (12)

Data collection: APEX2 (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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 (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026183/bh2361sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026183/bh2361Isup2.hkl

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

C26H28FNO4·1.5H2O	F(000) = 988
Mr = 464.52	Dx = 1.302 Mg m−3
Monoclinic, C2	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: C 2y	Cell parameters from 6582 reflections
a = 18.0155 (3) Å	θ = 2.6–64.7°
b = 7.6776 (1) Å	µ = 0.79 mm−1
c = 18.1506 (4) Å	T = 133 K
β = 109.324 (1)°	Block, colourless
V = 2369.08 (7) Å3	0.25 × 0.15 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	3415 independent reflections
Radiation source: fine-focus sealed tube	3402 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 65.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −20→21
Tmin = 0.826, Tmax = 0.925	k = −9→9
7232 measured reflections	l = −18→20

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.6114P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3415 reflections	Δρmax = 0.20 e Å−3
312 parameters	Δρmin = −0.18 e Å−3
1 restraint	Absolute structure: Flack (1983), 1359 Friedel pairs
0 constraints	Flack parameter: 0.05 (12)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
F1	0.49485 (7)	−0.26627 (16)	0.40332 (8)	0.0571 (3)
N1	−0.03356 (8)	0.4513 (2)	0.15607 (8)	0.0314 (3)
O1	0.26142 (6)	0.36402 (13)	0.34083 (6)	0.0237 (2)
O2	0.29280 (6)	0.57951 (14)	0.46321 (6)	0.0268 (2)
O3	0.32140 (7)	0.48228 (18)	0.15878 (7)	0.0392 (3)
O4	0.24651 (6)	0.74481 (15)	0.07306 (7)	0.0307 (3)
C1	0.21885 (8)	0.51681 (19)	0.33202 (9)	0.0217 (3)
C2	0.23288 (8)	0.6279 (2)	0.39717 (9)	0.0233 (3)
C3	0.18682 (9)	0.7742 (2)	0.39246 (9)	0.0265 (3)
H3	0.1968	0.8511	0.4357	0.032*
C4	0.12611 (8)	0.80691 (19)	0.32395 (9)	0.0253 (3)
H4	0.0943	0.9072	0.3209	0.030*
C5	0.10990 (8)	0.6993 (2)	0.25971 (9)	0.0239 (3)
C6	0.15775 (8)	0.55115 (19)	0.26184 (9)	0.0220 (3)
C7	0.13574 (8)	0.4223 (2)	0.19297 (9)	0.0254 (3)
C8	0.08177 (8)	0.5102 (2)	0.11800 (9)	0.0264 (3)
H8	0.0620	0.4171	0.0777	0.032*
C9	0.01057 (9)	0.5906 (2)	0.13270 (9)	0.0285 (3)
H9	−0.0244	0.6395	0.0820	0.034*
C10	0.03877 (8)	0.7424 (2)	0.18927 (9)	0.0279 (3)
H10A	0.0520	0.8416	0.1610	0.033*
H10B	−0.0048	0.7799	0.2075	0.033*
C11	0.20578 (9)	0.3494 (2)	0.17160 (9)	0.0275 (3)
H11A	0.2421	0.2888	0.2176	0.033*
H11B	0.1861	0.2628	0.1292	0.033*
C12	0.25034 (9)	0.4894 (2)	0.14564 (9)	0.0281 (3)
C13	0.20238 (9)	0.6325 (2)	0.09902 (9)	0.0266 (3)
C14	0.12457 (9)	0.6423 (2)	0.08562 (9)	0.0259 (3)
H14	0.0957	0.7353	0.0548	0.031*
C15	0.08761 (10)	0.2737 (2)	0.21185 (10)	0.0316 (4)
H15A	0.0736	0.1877	0.1688	0.038*
H15B	0.1198	0.2137	0.2601	0.038*
C16	0.01249 (10)	0.3444 (2)	0.22285 (10)	0.0330 (4)
H16A	−0.0202	0.2457	0.2293	0.040*
H16B	0.0267	0.4156	0.2710	0.040*
C17	0.31222 (10)	0.6993 (2)	0.52708 (9)	0.0332 (4)
H17A	0.3228	0.8142	0.5092	0.050*
H17B	0.3590	0.6580	0.5686	0.050*
H17C	0.2681	0.7079	0.5471	0.050*
C18	0.20598 (10)	0.8932 (2)	0.03173 (10)	0.0355 (4)
H18A	0.1646	0.8552	−0.0158	0.053*
H18B	0.2431	0.9685	0.0177	0.053*
H18C	0.1823	0.9579	0.0649	0.053*
C19	−0.10438 (10)	0.5180 (3)	0.16953 (12)	0.0392 (4)
H19A	−0.1362	0.4201	0.1767	0.059*
H19B	−0.1352	0.5874	0.1245	0.059*
H19C	−0.0890	0.5911	0.2164	0.059*
C20	0.34415 (9)	0.3842 (2)	0.35220 (9)	0.0273 (3)
H20A	0.3687	0.4621	0.3971	0.033*
H20B	0.3512	0.4367	0.3051	0.033*
C21	0.38241 (9)	0.2075 (2)	0.36728 (9)	0.0262 (3)
C22	0.46433 (10)	0.1988 (2)	0.39458 (10)	0.0323 (4)
H22	0.4942	0.3033	0.4049	0.039*
C23	0.50269 (10)	0.0401 (3)	0.40683 (11)	0.0394 (4)
H23	0.5585	0.0343	0.4250	0.047*
C24	0.45800 (11)	−0.1091 (3)	0.39200 (12)	0.0398 (4)
C25	0.37742 (11)	−0.1056 (2)	0.36530 (12)	0.0397 (4)
H25	0.3480	−0.2107	0.3556	0.048*
C26	0.33978 (10)	0.0545 (2)	0.35278 (11)	0.0335 (4)
H26	0.2839	0.0590	0.3340	0.040*
O2S	0.39668 (7)	0.7129 (2)	0.03873 (8)	0.0485 (4)
H21S	0.4268	0.7898	0.0802	0.043 (6)*
H22S	0.3668	0.6573	0.0628	0.131 (15)*
O1S	0.5000	0.4796 (3)	0.0000	0.0471 (5)
H11S	0.4712 (14)	0.555 (4)	0.0168 (15)	0.059 (7)*

	U11	U22	U33	U12	U13	U23
F1	0.0562 (6)	0.0372 (6)	0.0885 (9)	0.0217 (5)	0.0383 (6)	0.0200 (6)
N1	0.0288 (6)	0.0374 (8)	0.0294 (8)	−0.0071 (6)	0.0115 (5)	−0.0058 (6)
O1	0.0254 (5)	0.0206 (5)	0.0261 (6)	0.0017 (4)	0.0101 (4)	0.0017 (4)
O2	0.0308 (5)	0.0273 (5)	0.0195 (6)	0.0014 (4)	0.0045 (4)	−0.0017 (4)
O3	0.0355 (6)	0.0483 (8)	0.0397 (7)	0.0102 (5)	0.0205 (5)	0.0108 (6)
O4	0.0313 (5)	0.0316 (6)	0.0331 (6)	−0.0011 (5)	0.0158 (4)	0.0059 (5)
C1	0.0241 (6)	0.0198 (7)	0.0241 (8)	−0.0004 (5)	0.0117 (5)	0.0022 (6)
C2	0.0244 (7)	0.0244 (7)	0.0219 (8)	−0.0044 (6)	0.0088 (6)	0.0001 (6)
C3	0.0298 (7)	0.0260 (8)	0.0253 (8)	−0.0044 (6)	0.0113 (6)	−0.0051 (6)
C4	0.0258 (7)	0.0220 (7)	0.0299 (9)	0.0000 (6)	0.0117 (6)	−0.0004 (6)
C5	0.0223 (6)	0.0252 (8)	0.0251 (8)	−0.0033 (6)	0.0091 (6)	0.0035 (6)
C6	0.0248 (7)	0.0221 (7)	0.0215 (8)	−0.0046 (6)	0.0110 (6)	0.0005 (6)
C7	0.0310 (7)	0.0261 (8)	0.0194 (8)	−0.0040 (6)	0.0086 (6)	−0.0019 (6)
C8	0.0290 (7)	0.0287 (8)	0.0208 (8)	−0.0043 (6)	0.0072 (6)	−0.0022 (6)
C9	0.0263 (7)	0.0342 (9)	0.0230 (9)	−0.0044 (7)	0.0056 (6)	−0.0004 (7)
C10	0.0259 (7)	0.0294 (8)	0.0271 (9)	0.0014 (6)	0.0070 (6)	0.0018 (6)
C11	0.0398 (8)	0.0236 (8)	0.0207 (8)	0.0012 (6)	0.0120 (6)	−0.0038 (6)
C12	0.0346 (8)	0.0314 (9)	0.0214 (8)	0.0022 (7)	0.0138 (6)	−0.0038 (6)
C13	0.0330 (7)	0.0301 (8)	0.0188 (8)	−0.0025 (6)	0.0113 (6)	−0.0019 (6)
C14	0.0311 (7)	0.0286 (8)	0.0165 (8)	−0.0042 (6)	0.0060 (6)	−0.0013 (6)
C15	0.0391 (8)	0.0270 (8)	0.0289 (9)	−0.0083 (7)	0.0115 (7)	−0.0035 (7)
C16	0.0371 (8)	0.0350 (9)	0.0296 (9)	−0.0130 (7)	0.0145 (6)	−0.0028 (7)
C17	0.0426 (9)	0.0300 (8)	0.0216 (9)	−0.0040 (7)	0.0034 (6)	−0.0033 (6)
C18	0.0374 (8)	0.0350 (9)	0.0336 (10)	−0.0049 (8)	0.0109 (7)	0.0074 (7)
C19	0.0319 (8)	0.0491 (11)	0.0393 (10)	−0.0082 (8)	0.0154 (7)	−0.0081 (8)
C20	0.0284 (7)	0.0261 (8)	0.0310 (9)	−0.0007 (6)	0.0146 (6)	0.0020 (7)
C21	0.0332 (7)	0.0289 (8)	0.0215 (8)	0.0050 (6)	0.0156 (6)	0.0034 (6)
C22	0.0334 (8)	0.0355 (9)	0.0283 (9)	−0.0011 (7)	0.0104 (6)	−0.0009 (7)
C23	0.0343 (9)	0.0478 (11)	0.0369 (10)	0.0089 (8)	0.0128 (7)	0.0037 (8)
C24	0.0459 (9)	0.0355 (9)	0.0466 (11)	0.0143 (8)	0.0267 (8)	0.0149 (8)
C25	0.0448 (9)	0.0258 (8)	0.0596 (12)	0.0024 (8)	0.0322 (9)	0.0078 (8)
C26	0.0318 (8)	0.0301 (9)	0.0446 (10)	0.0029 (7)	0.0208 (7)	0.0054 (7)
O2S	0.0406 (6)	0.0605 (9)	0.0520 (8)	−0.0194 (7)	0.0256 (6)	−0.0300 (7)
O1S	0.0402 (10)	0.0401 (11)	0.0665 (14)	0.000	0.0251 (10)	0.000

F1—C24	1.360 (2)	C12—C13	1.479 (2)
N1—C19	1.469 (2)	C13—C14	1.343 (2)
N1—C16	1.471 (2)	C14—H14	0.9500
N1—C9	1.476 (2)	C15—C16	1.531 (2)
O1—C1	1.3815 (18)	C15—H15A	0.9900
O1—C20	1.4438 (17)	C15—H15B	0.9900
O2—C2	1.3725 (18)	C16—H16A	0.9900
O2—C17	1.430 (2)	C16—H16B	0.9900
O3—C12	1.2233 (19)	C17—H17A	0.9800
O4—C13	1.3585 (19)	C17—H17B	0.9800
O4—C18	1.425 (2)	C17—H17C	0.9800
C1—C6	1.406 (2)	C18—H18A	0.9800
C1—C2	1.411 (2)	C18—H18B	0.9800
C2—C3	1.383 (2)	C18—H18C	0.9800
C3—C4	1.380 (2)	C19—H19A	0.9800
C3—H3	0.9500	C19—H19B	0.9800
C4—C5	1.379 (2)	C19—H19C	0.9800
C4—H4	0.9500	C20—C21	1.505 (2)
C5—C6	1.420 (2)	C20—H20A	0.9900
C5—C10	1.517 (2)	C20—H20B	0.9900
C6—C7	1.540 (2)	C21—C26	1.381 (2)
C7—C15	1.539 (2)	C21—C22	1.394 (2)
C7—C8	1.542 (2)	C22—C23	1.381 (3)
C7—C11	1.543 (2)	C22—H22	0.9500
C8—C14	1.506 (2)	C23—C24	1.375 (3)
C8—C9	1.525 (2)	C23—H23	0.9500
C8—H8	1.0000	C24—C25	1.370 (3)
C9—C10	1.525 (2)	C25—C26	1.386 (3)
C9—H9	1.0000	C25—H25	0.9500
C10—H10A	0.9900	C26—H26	0.9500
C10—H10B	0.9900	O2S—H21S	0.9694
C11—C12	1.507 (2)	O2S—H22S	0.9051
C11—H11A	0.9900	O1S—H11S	0.90 (3)
C11—H11B	0.9900
C19—N1—C16	109.97 (14)	O4—C13—C12	111.83 (13)
C19—N1—C9	112.02 (14)	C13—C14—C8	122.02 (15)
C16—N1—C9	115.49 (12)	C13—C14—H14	119.0
C1—O1—C20	115.64 (11)	C8—C14—H14	119.0
C2—O2—C17	116.41 (12)	C16—C15—C7	110.70 (13)
C13—O4—C18	115.67 (12)	C16—C15—H15A	109.5
O1—C1—C6	120.15 (13)	C7—C15—H15A	109.5
O1—C1—C2	118.52 (12)	C16—C15—H15B	109.5
C6—C1—C2	121.03 (14)	C7—C15—H15B	109.5
O2—C2—C3	123.80 (14)	H15A—C15—H15B	108.1
O2—C2—C1	116.07 (13)	N1—C16—C15	111.84 (13)
C3—C2—C1	120.13 (13)	N1—C16—H16A	109.2
C4—C3—C2	118.93 (14)	C15—C16—H16A	109.2
C4—C3—H3	120.5	N1—C16—H16B	109.2
C2—C3—H3	120.5	C15—C16—H16B	109.2
C5—C4—C3	122.39 (14)	H16A—C16—H16B	107.9
C5—C4—H4	118.8	O2—C17—H17A	109.5
C3—C4—H4	118.8	O2—C17—H17B	109.5
C4—C5—C6	120.01 (13)	H17A—C17—H17B	109.5
C4—C5—C10	117.71 (14)	O2—C17—H17C	109.5
C6—C5—C10	122.25 (14)	H17A—C17—H17C	109.5
C1—C6—C5	117.47 (13)	H17B—C17—H17C	109.5
C1—C6—C7	121.96 (13)	O4—C18—H18A	109.5
C5—C6—C7	120.11 (13)	O4—C18—H18B	109.5
C15—C7—C6	107.95 (12)	H18A—C18—H18B	109.5
C15—C7—C8	106.49 (12)	O4—C18—H18C	109.5
C6—C7—C8	110.68 (13)	H18A—C18—H18C	109.5
C15—C7—C11	110.81 (13)	H18B—C18—H18C	109.5
C6—C7—C11	115.14 (12)	N1—C19—H19A	109.5
C8—C7—C11	105.44 (12)	N1—C19—H19B	109.5
C14—C8—C9	111.39 (13)	H19A—C19—H19B	109.5
C14—C8—C7	112.60 (12)	N1—C19—H19C	109.5
C9—C8—C7	110.14 (12)	H19A—C19—H19C	109.5
C14—C8—H8	107.5	H19B—C19—H19C	109.5
C9—C8—H8	107.5	O1—C20—C21	108.57 (12)
C7—C8—H8	107.5	O1—C20—H20A	110.0
N1—C9—C8	108.72 (13)	C21—C20—H20A	110.0
N1—C9—C10	116.85 (14)	O1—C20—H20B	110.0
C8—C9—C10	108.37 (12)	C21—C20—H20B	110.0
N1—C9—H9	107.5	H20A—C20—H20B	108.4
C8—C9—H9	107.5	C26—C21—C22	118.90 (15)
C10—C9—H9	107.5	C26—C21—C20	122.68 (13)
C5—C10—C9	113.63 (14)	C22—C21—C20	118.39 (15)
C5—C10—H10A	108.8	C23—C22—C21	120.94 (16)
C9—C10—H10A	108.8	C23—C22—H22	119.5
C5—C10—H10B	108.8	C21—C22—H22	119.5
C9—C10—H10B	108.8	C24—C23—C22	118.28 (15)
H10A—C10—H10B	107.7	C24—C23—H23	120.9
C12—C11—C7	112.63 (13)	C22—C23—H23	120.9
C12—C11—H11A	109.1	F1—C24—C25	118.55 (17)
C7—C11—H11A	109.1	F1—C24—C23	119.01 (15)
C12—C11—H11B	109.1	C25—C24—C23	122.44 (17)
C7—C11—H11B	109.1	C24—C25—C26	118.62 (17)
H11A—C11—H11B	107.8	C24—C25—H25	120.7
O3—C12—C13	121.36 (15)	C26—C25—H25	120.7
O3—C12—C11	122.58 (15)	C21—C26—C25	120.83 (15)
C13—C12—C11	115.97 (13)	C21—C26—H26	119.6
C14—C13—O4	126.68 (15)	C25—C26—H26	119.6
C14—C13—C12	121.49 (14)	H21S—O2S—H22S	100.4
C20—O1—C1—C6	117.00 (14)	C7—C8—C9—C10	67.54 (17)
C20—O1—C1—C2	−69.19 (16)	C4—C5—C10—C9	−161.88 (13)
C17—O2—C2—C3	−6.5 (2)	C6—C5—C10—C9	16.3 (2)
C17—O2—C2—C1	174.39 (13)	N1—C9—C10—C5	76.09 (17)
O1—C1—C2—O2	4.70 (18)	C8—C9—C10—C5	−47.08 (17)
C6—C1—C2—O2	178.46 (12)	C15—C7—C11—C12	174.84 (13)
O1—C1—C2—C3	−174.47 (12)	C6—C7—C11—C12	−62.30 (18)
C6—C1—C2—C3	−0.7 (2)	C8—C7—C11—C12	59.99 (16)
O2—C2—C3—C4	−177.53 (14)	C7—C11—C12—O3	146.72 (15)
C1—C2—C3—C4	1.6 (2)	C7—C11—C12—C13	−36.64 (19)
C2—C3—C4—C5	−0.4 (2)	C18—O4—C13—C14	4.3 (2)
C3—C4—C5—C6	−1.7 (2)	C18—O4—C13—C12	−176.15 (14)
C3—C4—C5—C10	176.50 (14)	O3—C12—C13—C14	−178.85 (14)
O1—C1—C6—C5	172.34 (12)	C11—C12—C13—C14	4.5 (2)
C2—C1—C6—C5	−1.31 (19)	O3—C12—C13—O4	1.6 (2)
O1—C1—C6—C7	0.16 (19)	C11—C12—C13—O4	−175.12 (12)
C2—C1—C6—C7	−173.49 (13)	O4—C13—C14—C8	−179.60 (15)
C4—C5—C6—C1	2.50 (19)	C12—C13—C14—C8	0.9 (2)
C10—C5—C6—C1	−175.63 (13)	C9—C8—C14—C13	150.28 (14)
C4—C5—C6—C7	174.83 (13)	C7—C8—C14—C13	26.0 (2)
C10—C5—C6—C7	−3.3 (2)	C6—C7—C15—C16	60.26 (16)
C1—C6—C7—C15	77.55 (16)	C8—C7—C15—C16	−58.62 (17)
C5—C6—C7—C15	−94.43 (16)	C11—C7—C15—C16	−172.80 (13)
C1—C6—C7—C8	−166.27 (12)	C19—N1—C16—C15	−179.28 (13)
C5—C6—C7—C8	21.76 (18)	C9—N1—C16—C15	−51.32 (19)
C1—C6—C7—C11	−46.83 (19)	C7—C15—C16—N1	52.98 (18)
C5—C6—C7—C11	141.20 (14)	C1—O1—C20—C21	175.38 (12)
C15—C7—C8—C14	−171.75 (13)	O1—C20—C21—C26	14.3 (2)
C6—C7—C8—C14	71.16 (16)	O1—C20—C21—C22	−167.91 (13)
C11—C7—C8—C14	−53.97 (17)	C26—C21—C22—C23	0.2 (2)
C15—C7—C8—C9	63.25 (16)	C20—C21—C22—C23	−177.70 (16)
C6—C7—C8—C9	−53.84 (16)	C21—C22—C23—C24	−0.5 (3)
C11—C7—C8—C9	−178.96 (12)	C22—C23—C24—F1	179.61 (18)
C19—N1—C9—C8	−178.64 (13)	C22—C23—C24—C25	0.4 (3)
C16—N1—C9—C8	54.42 (18)	F1—C24—C25—C26	−179.18 (17)
C19—N1—C9—C10	58.37 (18)	C23—C24—C25—C26	0.0 (3)
C16—N1—C9—C10	−68.57 (18)	C22—C21—C26—C25	0.2 (3)
C14—C8—C9—N1	173.90 (13)	C20—C21—C26—C25	178.05 (17)
C7—C8—C9—N1	−60.41 (17)	C24—C25—C26—C21	−0.4 (3)
C14—C8—C9—C10	−58.15 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O2S—H22S···O4	0.91	2.33	2.9805 (16)	128
O2S—H22S···O3	0.91	2.54	3.417 (2)	164
O1S—H11S···O2S	0.90 (3)	1.94 (3)	2.8342 (19)	172 (2)
O2S—H21S···N1i	0.97	1.81	2.7736 (19)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2S—H22S⋯O4	0.91	2.33	2.9805 (16)	128
O2S—H22S⋯O3	0.91	2.54	3.417 (2)	164
O1S—H11S⋯O2S	0.90 (3)	1.94 (3)	2.8342 (19)	172 (2)
O2S—H21S⋯N1i	0.97	1.81	2.7736 (19)	170

Symmetry code: (i) .