2-(N-Cyclo-hexyl-carbamo-yl)benzene-sulfonamide.

The asymmetric unit of the title compound, C(13)H(18)N(2)O(3)S, contains two mol-ecules with similar conformations. In both mol-ecules, the cyclo-hexyl rings adopt chair conformations, with the attached N atom in an equatorial orientation and an intra-molecular N-H⋯O hydrogen bond generates an S(7) ring. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules and a C-H⋯O hydrogen bond is also observed. The crystal studied was a racemic twin.

Related literature

For the biological activity of benzene­sulfonamide derivatives, see: Petrov et al. (2006 ▶); Eatedal et al. (2002 ▶); Ahmad et al. (2010 ▶). For related structures, see: Siddiqui et al. (2007 ▶, 2008 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C13H18N2O3S

M = 282.35

Orthorhombic,

a = 16.1869 (5) Å

b = 10.8467 (3) Å

c = 15.9353 (4) Å

V = 2797.83 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 173 K

0.20 × 0.14 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.954, T max = 0.981

5929 measured reflections

5929 independent reflections

5451 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.110

S = 1.14

5929 reflections

362 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶)

Flack parameter: 0.52 (8)

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000633/hb6585sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000633/hb6585Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000633/hb6585Isup3.cml

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

C13H18N2O3S	F(000) = 1200
Mr = 282.35	Dx = 1.341 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3423 reflections
a = 16.1869 (5) Å	θ = 1.0–27.5°
b = 10.8467 (3) Å	µ = 0.24 mm−1
c = 15.9353 (4) Å	T = 173 K
V = 2797.83 (13) Å3	Prism, pale-yellow
Z = 8	0.20 × 0.14 × 0.08 mm

Nonius KappaCCD diffractometer	5929 independent reflections
Radiation source: fine-focus sealed tube	5451 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω and φ scans	θmax = 27.4°, θmin = 2.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −20→20
Tmin = 0.954, Tmax = 0.981	k = −14→14
5929 measured reflections	l = −20→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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.009P)2 + 3.8318P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
5929 reflections	Δρmax = 0.31 e Å−3
362 parameters	Δρmin = −0.28 e Å−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.52 (8)

Experimental. IR (KBr, max, cm-1) NH2 & NH 3318, 3275; CO 1680; SO2 1320 and 1155; 1H-NMR (300 MHz, Methanol -d4) δ: 1.30–1.75 (m, 10H, cyclohexyl), 3.35 (m, 1H, cyclohexyl-CH), 5.55 (s, 2H, NH2), 7.73–8.13 (m, 4H, C6H4); 13C-NMR δ: 167.5, 137.5, 133.4, 131.9, 131.5, 127.7, 127.3, 45.7, 34.5, 27.3, 22.7

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
S1	0.34082 (5)	0.60650 (7)	0.55872 (6)	0.02820 (16)
S2	0.25588 (6)	−0.07073 (7)	0.31713 (6)	0.03103 (18)
O1	0.40724 (14)	0.5355 (2)	0.59198 (15)	0.0357 (6)
O2	0.31913 (17)	0.7220 (2)	0.59666 (17)	0.0440 (7)
O3	0.36076 (14)	0.3676 (2)	0.43341 (13)	0.0287 (5)
O4	0.27815 (17)	−0.1884 (2)	0.35130 (19)	0.0493 (7)
O5	0.20767 (16)	0.0130 (2)	0.36603 (16)	0.0394 (6)
O6	0.21853 (14)	0.1570 (2)	0.19541 (13)	0.0276 (5)
N1	0.3621 (2)	0.6352 (3)	0.46194 (19)	0.0330 (7)
H11N	0.327 (3)	0.690 (4)	0.437 (2)	0.040*
H12N	0.369 (3)	0.568 (4)	0.434 (3)	0.040*
N2	0.35953 (18)	0.2310 (2)	0.54146 (17)	0.0294 (6)
H2N	0.335 (2)	0.212 (4)	0.591 (3)	0.035*
N3	0.2057 (2)	−0.0976 (3)	0.2323 (2)	0.0355 (7)
H31N	0.201 (3)	−0.034 (4)	0.202 (3)	0.043*
H32N	0.222 (3)	−0.163 (4)	0.205 (3)	0.043*
N4	0.25528 (18)	0.3051 (2)	0.28838 (17)	0.0260 (6)
H4N	0.290 (2)	0.325 (3)	0.326 (2)	0.031*
C1	0.25169 (19)	0.5111 (3)	0.5624 (2)	0.0257 (6)
C2	0.1783 (2)	0.5611 (3)	0.5923 (2)	0.0353 (8)
H2	0.1768	0.6444	0.6106	0.042*
C3	0.1075 (2)	0.4899 (4)	0.5954 (3)	0.0407 (9)
H3	0.0571	0.5248	0.6146	0.049*
C4	0.1101 (2)	0.3689 (3)	0.5706 (3)	0.0392 (8)
H4	0.0613	0.3203	0.5722	0.047*
C5	0.1834 (2)	0.3174 (3)	0.5434 (2)	0.0339 (8)
H5	0.1846	0.2328	0.5280	0.041*
C6	0.2557 (2)	0.3867 (3)	0.53812 (19)	0.0269 (7)
C7	0.3311 (2)	0.3281 (3)	0.5007 (2)	0.0262 (7)
C8	0.4304 (2)	0.1578 (3)	0.5131 (2)	0.0295 (7)
H8	0.4268	0.1483	0.4508	0.035*
C9	0.4254 (2)	0.0303 (3)	0.5529 (3)	0.0418 (9)
H9A	0.3743	−0.0114	0.5340	0.050*
H9B	0.4227	0.0388	0.6147	0.050*
C10	0.5003 (3)	−0.0486 (4)	0.5294 (3)	0.0558 (12)
H10A	0.4980	−0.1273	0.5608	0.067*
H10B	0.4979	−0.0681	0.4688	0.067*
C11	0.5804 (3)	0.0149 (4)	0.5482 (3)	0.0551 (11)
H11A	0.6267	−0.0367	0.5279	0.066*
H11B	0.5864	0.0244	0.6097	0.066*
C12	0.5848 (3)	0.1414 (4)	0.5067 (3)	0.0455 (9)
H12A	0.5843	0.1317	0.4449	0.055*
H12B	0.6369	0.1828	0.5227	0.055*
C13	0.5111 (2)	0.2206 (3)	0.5341 (2)	0.0361 (8)
H13A	0.5140	0.2353	0.5953	0.043*
H13B	0.5136	0.3015	0.5054	0.043*
C14	0.34848 (19)	0.0091 (3)	0.2919 (2)	0.0239 (6)
C15	0.4234 (2)	−0.0517 (3)	0.3024 (2)	0.0346 (8)
H15	0.4241	−0.1355	0.3196	0.042*
C16	0.4974 (2)	0.0098 (3)	0.2877 (2)	0.0351 (8)
H16	0.5486	−0.0319	0.2942	0.042*
C17	0.4956 (2)	0.1325 (3)	0.2636 (2)	0.0327 (8)
H17	0.5459	0.1750	0.2532	0.039*
C18	0.4208 (2)	0.1936 (3)	0.2545 (2)	0.0296 (7)
H18	0.4206	0.2782	0.2392	0.035*
C19	0.34610 (19)	0.1327 (3)	0.26748 (18)	0.0227 (6)
C20	0.26705 (18)	0.1994 (3)	0.24848 (18)	0.0221 (6)
C21	0.1806 (2)	0.3805 (3)	0.2773 (2)	0.0264 (7)
H21	0.1713	0.3936	0.2159	0.032*
C22	0.1946 (2)	0.5054 (3)	0.3188 (2)	0.0324 (7)
H22A	0.2100	0.4929	0.3783	0.039*
H22B	0.2410	0.5479	0.2905	0.039*
C23	0.1177 (2)	0.5864 (3)	0.3142 (2)	0.0354 (8)
H23A	0.1275	0.6635	0.3460	0.042*
H23B	0.1069	0.6088	0.2550	0.042*
C24	0.0428 (2)	0.5213 (4)	0.3498 (3)	0.0426 (9)
H24A	−0.0066	0.5740	0.3426	0.051*
H24B	0.0509	0.5070	0.4106	0.051*
C25	0.0290 (2)	0.3983 (4)	0.3057 (3)	0.0459 (10)
H25A	−0.0192	0.3559	0.3309	0.055*
H25B	0.0170	0.4128	0.2456	0.055*
C26	0.1052 (2)	0.3169 (3)	0.3139 (3)	0.0346 (7)
H26A	0.1151	0.2982	0.3739	0.042*
H26B	0.0956	0.2381	0.2841	0.042*

	U11	U22	U33	U12	U13	U23
S1	0.0271 (4)	0.0283 (3)	0.0292 (4)	−0.0026 (3)	−0.0003 (3)	−0.0022 (3)
S2	0.0288 (4)	0.0271 (4)	0.0372 (4)	−0.0029 (4)	−0.0010 (4)	0.0083 (4)
O1	0.0255 (12)	0.0457 (14)	0.0359 (13)	−0.0016 (10)	−0.0031 (10)	0.0036 (11)
O2	0.0453 (15)	0.0363 (14)	0.0504 (16)	−0.0056 (12)	0.0067 (13)	−0.0126 (12)
O3	0.0335 (12)	0.0273 (11)	0.0253 (12)	0.0013 (9)	0.0015 (9)	0.0036 (9)
O4	0.0457 (16)	0.0363 (14)	0.0660 (19)	−0.0054 (12)	−0.0088 (14)	0.0238 (13)
O5	0.0355 (13)	0.0477 (15)	0.0351 (14)	−0.0036 (12)	0.0101 (11)	0.0036 (11)
O6	0.0307 (12)	0.0239 (11)	0.0282 (12)	0.0004 (9)	−0.0059 (9)	−0.0009 (9)
N1	0.0382 (17)	0.0278 (15)	0.0330 (16)	−0.0030 (13)	0.0030 (13)	0.0038 (12)
N2	0.0365 (16)	0.0249 (13)	0.0270 (15)	0.0062 (12)	0.0058 (12)	0.0034 (11)
N3	0.0340 (17)	0.0258 (15)	0.0467 (19)	−0.0033 (13)	−0.0067 (14)	0.0005 (13)
N4	0.0262 (13)	0.0235 (13)	0.0283 (14)	0.0039 (11)	−0.0071 (11)	−0.0022 (10)
C1	0.0236 (13)	0.0287 (14)	0.0247 (14)	−0.0002 (12)	0.0000 (13)	0.0030 (15)
C2	0.0307 (17)	0.0348 (18)	0.040 (2)	0.0048 (15)	0.0029 (15)	0.0011 (15)
C3	0.0252 (17)	0.052 (2)	0.045 (2)	0.0103 (16)	0.0064 (15)	0.0092 (17)
C4	0.0281 (17)	0.045 (2)	0.045 (2)	−0.0094 (15)	0.0008 (16)	0.0169 (18)
C5	0.0335 (18)	0.0302 (16)	0.038 (2)	−0.0062 (14)	−0.0009 (14)	0.0058 (14)
C6	0.0265 (15)	0.0297 (15)	0.0244 (16)	0.0004 (13)	−0.0024 (12)	0.0059 (12)
C7	0.0296 (17)	0.0225 (15)	0.0265 (16)	−0.0018 (13)	−0.0023 (13)	−0.0020 (12)
C8	0.0380 (19)	0.0266 (16)	0.0240 (16)	0.0057 (14)	0.0051 (13)	0.0027 (13)
C9	0.051 (2)	0.0281 (17)	0.046 (2)	0.0075 (15)	0.0052 (19)	0.0097 (17)
C10	0.075 (3)	0.035 (2)	0.057 (3)	0.024 (2)	0.013 (2)	0.0082 (19)
C11	0.054 (3)	0.060 (3)	0.051 (3)	0.033 (2)	0.009 (2)	0.007 (2)
C12	0.039 (2)	0.049 (2)	0.048 (2)	0.0136 (18)	0.0046 (18)	−0.0036 (19)
C13	0.0355 (19)	0.0340 (18)	0.0390 (19)	0.0084 (15)	0.0028 (15)	−0.0044 (15)
C14	0.0219 (14)	0.0214 (14)	0.0285 (16)	−0.0033 (12)	−0.0027 (12)	−0.0006 (11)
C15	0.0361 (19)	0.0261 (16)	0.042 (2)	0.0023 (14)	−0.0063 (15)	0.0001 (14)
C16	0.0244 (15)	0.0324 (17)	0.049 (2)	0.0046 (13)	−0.0031 (15)	−0.0066 (16)
C17	0.0232 (16)	0.0336 (17)	0.041 (2)	−0.0069 (14)	−0.0008 (14)	−0.0046 (15)
C18	0.0326 (17)	0.0268 (16)	0.0293 (17)	−0.0031 (14)	−0.0014 (14)	−0.0017 (13)
C19	0.0263 (15)	0.0217 (14)	0.0201 (14)	0.0024 (12)	−0.0011 (12)	−0.0033 (11)
C20	0.0233 (15)	0.0210 (14)	0.0221 (15)	−0.0002 (11)	0.0021 (12)	0.0014 (11)
C21	0.0276 (16)	0.0235 (15)	0.0282 (16)	0.0030 (12)	0.0007 (13)	−0.0014 (13)
C22	0.0349 (17)	0.0251 (16)	0.0372 (18)	0.0009 (13)	−0.0013 (15)	0.0000 (15)
C23	0.049 (2)	0.0245 (16)	0.0329 (18)	0.0110 (15)	0.0021 (17)	−0.0016 (15)
C24	0.045 (2)	0.039 (2)	0.043 (2)	0.0157 (17)	0.0108 (17)	0.0005 (17)
C25	0.0315 (19)	0.044 (2)	0.062 (3)	0.0031 (16)	0.0074 (18)	−0.0036 (19)
C26	0.0362 (19)	0.0271 (16)	0.0406 (19)	0.0022 (14)	0.0025 (16)	−0.0006 (15)

S1—O1	1.425 (2)	C10—H10A	0.9900
S1—O2	1.434 (3)	C10—H10B	0.9900
S1—N1	1.610 (3)	C11—C12	1.525 (6)
S1—C1	1.777 (3)	C11—H11A	0.9900
S2—O5	1.428 (3)	C11—H11B	0.9900
S2—O4	1.434 (3)	C12—C13	1.534 (5)
S2—N3	1.604 (3)	C12—H12A	0.9900
S2—C14	1.777 (3)	C12—H12B	0.9900
O3—C7	1.252 (4)	C13—H13A	0.9900
O6—C20	1.242 (4)	C13—H13B	0.9900
N1—H11N	0.92 (4)	C14—C15	1.390 (4)
N1—H12N	0.86 (4)	C14—C19	1.397 (4)
N2—C7	1.320 (4)	C15—C16	1.390 (5)
N2—C8	1.467 (4)	C15—H15	0.9500
N2—H2N	0.91 (4)	C16—C17	1.385 (5)
N3—H31N	0.85 (4)	C16—H16	0.9500
N3—H32N	0.88 (4)	C17—C18	1.387 (5)
N4—C20	1.325 (4)	C17—H17	0.9500
N4—C21	1.470 (4)	C18—C19	1.393 (4)
N4—H4N	0.85 (4)	C18—H18	0.9500
C1—C2	1.390 (4)	C19—C20	1.501 (4)
C1—C6	1.405 (4)	C21—C26	1.518 (5)
C2—C3	1.382 (5)	C21—C22	1.525 (4)
C2—H2	0.9500	C21—H21	1.0000
C3—C4	1.371 (6)	C22—C23	1.525 (4)
C3—H3	0.9500	C22—H22A	0.9900
C4—C5	1.381 (5)	C22—H22B	0.9900
C4—H4	0.9500	C23—C24	1.513 (5)
C5—C6	1.393 (4)	C23—H23A	0.9900
C5—H5	0.9500	C23—H23B	0.9900
C6—C7	1.500 (4)	C24—C25	1.524 (5)
C8—C13	1.510 (5)	C24—H24A	0.9900
C8—C9	1.524 (4)	C24—H24B	0.9900
C8—H8	1.0000	C25—C26	1.521 (5)
C9—C10	1.531 (5)	C25—H25A	0.9900
C9—H9A	0.9900	C25—H25B	0.9900
C9—H9B	0.9900	C26—H26A	0.9900
C10—C11	1.498 (7)	C26—H26B	0.9900
O1—S1—O2	120.00 (16)	C11—C12—C13	110.1 (3)
O1—S1—N1	107.43 (16)	C11—C12—H12A	109.6
O2—S1—N1	106.70 (17)	C13—C12—H12A	109.6
O1—S1—C1	106.58 (14)	C11—C12—H12B	109.6
O2—S1—C1	107.23 (15)	C13—C12—H12B	109.6
N1—S1—C1	108.50 (16)	H12A—C12—H12B	108.1
O5—S2—O4	119.74 (18)	C8—C13—C12	110.9 (3)
O5—S2—N3	107.38 (17)	C8—C13—H13A	109.5
O4—S2—N3	106.62 (17)	C12—C13—H13A	109.5
O5—S2—C14	105.93 (15)	C8—C13—H13B	109.5
O4—S2—C14	107.90 (16)	C12—C13—H13B	109.5
N3—S2—C14	108.96 (17)	H13A—C13—H13B	108.0
S1—N1—H11N	114 (2)	C15—C14—C19	120.8 (3)
S1—N1—H12N	112 (3)	C15—C14—S2	118.6 (3)
H11N—N1—H12N	113 (4)	C19—C14—S2	120.5 (2)
C7—N2—C8	123.6 (3)	C16—C15—C14	120.3 (3)
C7—N2—H2N	117 (2)	C16—C15—H15	119.9
C8—N2—H2N	119 (2)	C14—C15—H15	119.9
S2—N3—H31N	112 (3)	C17—C16—C15	119.3 (3)
S2—N3—H32N	114 (3)	C17—C16—H16	120.4
H31N—N3—H32N	114 (4)	C15—C16—H16	120.4
C20—N4—C21	122.8 (3)	C16—C17—C18	120.4 (3)
C20—N4—H4N	118 (2)	C16—C17—H17	119.8
C21—N4—H4N	119 (2)	C18—C17—H17	119.8
C2—C1—C6	120.5 (3)	C17—C18—C19	121.0 (3)
C2—C1—S1	118.5 (2)	C17—C18—H18	119.5
C6—C1—S1	120.9 (2)	C19—C18—H18	119.5
C3—C2—C1	120.2 (3)	C18—C19—C14	118.2 (3)
C3—C2—H2	119.9	C18—C19—C20	118.8 (3)
C1—C2—H2	119.9	C14—C19—C20	122.8 (3)
C4—C3—C2	119.9 (3)	O6—C20—N4	123.8 (3)
C4—C3—H3	120.1	O6—C20—C19	119.9 (3)
C2—C3—H3	120.1	N4—C20—C19	116.3 (3)
C3—C4—C5	120.3 (3)	N4—C21—C26	111.3 (3)
C3—C4—H4	119.9	N4—C21—C22	108.6 (3)
C5—C4—H4	119.9	C26—C21—C22	110.9 (3)
C4—C5—C6	121.5 (3)	N4—C21—H21	108.6
C4—C5—H5	119.3	C26—C21—H21	108.6
C6—C5—H5	119.3	C22—C21—H21	108.6
C5—C6—C1	117.6 (3)	C23—C22—C21	111.7 (3)
C5—C6—C7	118.6 (3)	C23—C22—H22A	109.3
C1—C6—C7	123.6 (3)	C21—C22—H22A	109.3
O3—C7—N2	124.1 (3)	C23—C22—H22B	109.3
O3—C7—C6	120.5 (3)	C21—C22—H22B	109.3
N2—C7—C6	115.3 (3)	H22A—C22—H22B	107.9
N2—C8—C13	111.3 (3)	C24—C23—C22	111.5 (3)
N2—C8—C9	108.7 (3)	C24—C23—H23A	109.3
C13—C8—C9	111.3 (3)	C22—C23—H23A	109.3
N2—C8—H8	108.5	C24—C23—H23B	109.3
C13—C8—H8	108.5	C22—C23—H23B	109.3
C9—C8—H8	108.5	H23A—C23—H23B	108.0
C8—C9—C10	111.3 (3)	C23—C24—C25	110.7 (3)
C8—C9—H9A	109.4	C23—C24—H24A	109.5
C10—C9—H9A	109.4	C25—C24—H24A	109.5
C8—C9—H9B	109.4	C23—C24—H24B	109.5
C10—C9—H9B	109.4	C25—C24—H24B	109.5
H9A—C9—H9B	108.0	H24A—C24—H24B	108.1
C11—C10—C9	112.3 (3)	C26—C25—C24	110.5 (3)
C11—C10—H10A	109.1	C26—C25—H25A	109.6
C9—C10—H10A	109.1	C24—C25—H25A	109.6
C11—C10—H10B	109.1	C26—C25—H25B	109.6
C9—C10—H10B	109.1	C24—C25—H25B	109.6
H10A—C10—H10B	107.9	H25A—C25—H25B	108.1
C10—C11—C12	111.5 (3)	C21—C26—C25	110.8 (3)
C10—C11—H11A	109.3	C21—C26—H26A	109.5
C12—C11—H11A	109.3	C25—C26—H26A	109.5
C10—C11—H11B	109.3	C21—C26—H26B	109.5
C12—C11—H11B	109.3	C25—C26—H26B	109.5
H11A—C11—H11B	108.0	H26A—C26—H26B	108.1
O1—S1—C1—C2	134.7 (3)	O5—S2—C14—C15	133.5 (3)
O2—S1—C1—C2	5.0 (3)	O4—S2—C14—C15	4.1 (3)
N1—S1—C1—C2	−109.9 (3)	N3—S2—C14—C15	−111.3 (3)
O1—S1—C1—C6	−43.4 (3)	O5—S2—C14—C19	−42.3 (3)
O2—S1—C1—C6	−173.1 (3)	O4—S2—C14—C19	−171.7 (3)
N1—S1—C1—C6	72.0 (3)	N3—S2—C14—C19	72.9 (3)
C6—C1—C2—C3	−2.5 (6)	C19—C14—C15—C16	−0.7 (5)
S1—C1—C2—C3	179.4 (3)	S2—C14—C15—C16	−176.5 (3)
C1—C2—C3—C4	1.5 (6)	C14—C15—C16—C17	0.8 (5)
C2—C3—C4—C5	0.6 (6)	C15—C16—C17—C18	0.3 (5)
C3—C4—C5—C6	−1.7 (6)	C16—C17—C18—C19	−1.4 (5)
C4—C5—C6—C1	0.7 (5)	C17—C18—C19—C14	1.5 (5)
C4—C5—C6—C7	−174.5 (3)	C17—C18—C19—C20	−173.9 (3)
C2—C1—C6—C5	1.4 (5)	C15—C14—C19—C18	−0.5 (4)
S1—C1—C6—C5	179.4 (2)	S2—C14—C19—C18	175.3 (2)
C2—C1—C6—C7	176.4 (3)	C15—C14—C19—C20	174.8 (3)
S1—C1—C6—C7	−5.6 (5)	S2—C14—C19—C20	−9.5 (4)
C8—N2—C7—O3	0.7 (5)	C21—N4—C20—O6	3.6 (5)
C8—N2—C7—C6	177.3 (3)	C21—N4—C20—C19	−179.2 (3)
C5—C6—C7—O3	114.7 (3)	C18—C19—C20—O6	120.3 (3)
C1—C6—C7—O3	−60.2 (4)	C14—C19—C20—O6	−55.0 (4)
C5—C6—C7—N2	−62.1 (4)	C18—C19—C20—N4	−57.0 (4)
C1—C6—C7—N2	123.0 (3)	C14—C19—C20—N4	127.7 (3)
C7—N2—C8—C13	78.8 (4)	C20—N4—C21—C26	68.3 (4)
C7—N2—C8—C9	−158.2 (3)	C20—N4—C21—C22	−169.3 (3)
N2—C8—C9—C10	−177.0 (3)	N4—C21—C22—C23	−176.7 (3)
C13—C8—C9—C10	−54.0 (4)	C26—C21—C22—C23	−54.1 (4)
C8—C9—C10—C11	53.1 (5)	C21—C22—C23—C24	54.0 (4)
C9—C10—C11—C12	−54.6 (5)	C22—C23—C24—C25	−55.5 (4)
C10—C11—C12—C13	56.3 (5)	C23—C24—C25—C26	57.6 (4)
N2—C8—C13—C12	178.2 (3)	N4—C21—C26—C25	177.4 (3)
C9—C8—C13—C12	56.7 (4)	C22—C21—C26—C25	56.3 (4)
C11—C12—C13—C8	−57.4 (4)	C24—C25—C26—C21	−58.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11N···O4i	0.92 (4)	2.05 (4)	2.935 (4)	161 (4)
N2—H2N···O6ii	0.91 (4)	1.96 (4)	2.874 (4)	175 (4)
N3—H32N···O2iii	0.88 (4)	2.23 (4)	2.943 (4)	138 (4)
C3—H3···O1iv	0.95	2.54	3.254 (4)	132.
N1—H12N···O3	0.86 (4)	2.18 (4)	2.938 (4)	146 (4)
N3—H31N···O6	0.85 (4)	2.09 (4)	2.831 (4)	145 (4)
N4—H4N···O3	0.85 (4)	2.11 (4)	2.952 (4)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11N⋯O4i	0.92 (4)	2.05 (4)	2.935 (4)	161 (4)
N2—H2N⋯O6ii	0.91 (4)	1.96 (4)	2.874 (4)	175 (4)
N3—H32N⋯O2iii	0.88 (4)	2.23 (4)	2.943 (4)	138 (4)
C3—H3⋯O1iv	0.95	2.54	3.254 (4)	132
N1—H12N⋯O3	0.86 (4)	2.18 (4)	2.938 (4)	146 (4)
N3—H31N⋯O6	0.85 (4)	2.09 (4)	2.831 (4)	145 (4)
N4—H4N⋯O3	0.85 (4)	2.11 (4)	2.952 (4)	171 (3)

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