cis-N-(2-Hydroxy-cyclo-hexyl)-p-toluene-sulfonamide.

There are two symmetry-independent mol-ecules in the asymmetric unit of the title compound, C(13)H(19)NO(3)S. The cyclo-hexane rings in the two mol-ecules adopt chair configurations. The hydr-oxy and amino groups on the cyclo-hexane ring assume axial and equatorial orientations, respectively, with respect to the plane of the ring. The crystal structure is stabilized by two inter-molecular N-H⋯O and O-H⋯O hydrogen bonds from the two symmetry-independent mol-ecules.

Related literature

For related structures of β-amino alcohols, see: Bergmeier (2000 ▶); Krzemiński & Wojtczak (2005 ▶). For related structures of tosyl­amino compounds, see: Coote et al. (2008 ▶); Liu et al. (2005 ▶); Chinnakali et al. (2007 ▶); Nan & Xing (2006 ▶). For the synthesis of the title compound, see: Naiker et al. (2008 ▶).

Experimental

Crystal data

C13H19NO3S

M = 269.35

Triclinic,

a = 6.3031 (1) Å

b = 12.8355 (2) Å

c = 17.5367 (3) Å

α = 106.645 (1)°

β = 93.971 (1)°

γ = 100.047 (1)°

V = 1327.75 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 173 K

0.51 × 0.31 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

18458 measured reflections

6423 independent reflections

4837 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.111

S = 1.07

6423 reflections

343 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002151/lx2131sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002151/lx2131Isup2.hkl

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

C13H19NO3S	Z = 4
Mr = 269.35	F(000) = 576
Triclinic, P1	Dx = 1.347 Mg m−3
Hall symbol: -P 1	Melting point = 414–416 K
a = 6.3031 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.8355 (2) Å	Cell parameters from 6946 reflections
c = 17.5367 (3) Å	θ = 2.4–28.3°
α = 106.645 (1)°	µ = 0.24 mm−1
β = 93.971 (1)°	T = 173 K
γ = 100.047 (1)°	Block, colourless
V = 1327.75 (4) Å3	0.51 × 0.31 × 0.25 mm

Bruker APEXII CCD diffractometer	4837 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 28.0°, θmin = 1.2°
φ and ω scans	h = −8→8
18458 measured reflections	k = −16→16
6423 independent reflections	l = −23→23

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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.0739P] where P = (Fo2 + 2Fc2)/3
6423 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.41 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
C1	0.3149 (2)	0.39725 (12)	0.35318 (8)	0.0230 (3)
H1	0.4155	0.4675	0.3860	0.028*
C2	0.4327 (2)	0.30139 (12)	0.34741 (9)	0.0227 (3)
H2	0.5706	0.3156	0.3236	0.027*
C3	0.4842 (3)	0.28788 (14)	0.42986 (9)	0.0303 (4)
H3A	0.5896	0.3543	0.4639	0.036*
H3B	0.5522	0.2225	0.4240	0.036*
C4	0.2795 (3)	0.27272 (15)	0.47095 (10)	0.0344 (4)
H4A	0.1800	0.2022	0.4399	0.041*
H4B	0.3195	0.2684	0.5254	0.041*
C5	0.1644 (3)	0.36911 (14)	0.47692 (9)	0.0337 (4)
H5A	0.2583	0.4384	0.5127	0.040*
H5B	0.0285	0.3557	0.5009	0.040*
C6	0.1107 (3)	0.38351 (13)	0.39456 (9)	0.0266 (3)
H6A	0.0034	0.3178	0.3607	0.032*
H6B	0.0449	0.4497	0.4010	0.032*
C7	0.3445 (2)	0.63056 (12)	0.29981 (8)	0.0212 (3)
C8	0.5061 (2)	0.72537 (12)	0.31511 (9)	0.0238 (3)
H8	0.6421	0.7204	0.2956	0.029*
C9	0.4672 (3)	0.82718 (12)	0.35906 (9)	0.0282 (3)
H9	0.5775	0.8920	0.3693	0.034*
C10	0.2692 (3)	0.83612 (13)	0.38840 (9)	0.0290 (4)
C11	0.1103 (3)	0.74045 (14)	0.37164 (10)	0.0310 (4)
H11	−0.0257	0.7454	0.3911	0.037*
C12	0.1439 (3)	0.63787 (13)	0.32735 (9)	0.0284 (3)
H12	0.0320	0.5735	0.3159	0.034*
C13	0.2270 (4)	0.94682 (16)	0.43611 (11)	0.0459 (5)
H13A	0.0900	0.9582	0.4130	0.069*
H13B	0.3460	1.0061	0.4345	0.069*
H13C	0.2173	0.9480	0.4919	0.069*
N1	0.2596 (2)	0.40722 (10)	0.27298 (8)	0.0243 (3)
O1	0.30664 (19)	0.48034 (9)	0.15979 (6)	0.0319 (3)
O2	0.62179 (17)	0.50634 (9)	0.26023 (7)	0.0322 (3)
O3	0.29042 (18)	0.20373 (9)	0.29512 (6)	0.0262 (2)
S1	0.39239 (6)	0.50145 (3)	0.24179 (2)	0.02302 (10)
H1N	0.134 (3)	0.3817 (15)	0.2496 (11)	0.039 (5)*
H3O	0.364 (3)	0.1556 (18)	0.2813 (12)	0.050 (6)*
C14	0.7984 (3)	1.13220 (12)	0.14293 (9)	0.0260 (3)
H14	0.6960	1.0621	0.1109	0.031*
C15	0.6821 (2)	1.22875 (12)	0.14932 (8)	0.0221 (3)
H15	0.5435	1.2142	0.1726	0.026*
C16	0.6321 (3)	1.24306 (13)	0.06696 (9)	0.0275 (3)
H16A	0.5649	1.3087	0.0729	0.033*
H16B	0.5267	1.1769	0.0325	0.033*
C17	0.8384 (3)	1.25814 (14)	0.02681 (9)	0.0311 (4)
H17A	0.8013	1.2657	−0.0269	0.037*
H17B	0.9405	1.3268	0.0594	0.037*
C18	0.9460 (3)	1.15881 (15)	0.01851 (10)	0.0382 (4)
H18A	1.0803	1.1699	−0.0068	0.046*
H18B	0.8468	1.0909	−0.0167	0.046*
C19	1.0017 (3)	1.14389 (14)	0.10043 (10)	0.0322 (4)
H19A	1.1115	1.2088	0.1339	0.039*
H19B	1.0647	1.0768	0.0934	0.039*
C20	0.7614 (2)	0.89890 (11)	0.20252 (8)	0.0214 (3)
C21	0.5911 (3)	0.82342 (12)	0.15054 (9)	0.0253 (3)
H21	0.4570	0.8445	0.1409	0.030*
C22	0.6186 (3)	0.71642 (13)	0.11252 (9)	0.0290 (3)
H22	0.5021	0.6643	0.0769	0.035*
C23	0.8145 (3)	0.68457 (12)	0.12593 (9)	0.0276 (3)
C24	0.9834 (3)	0.76236 (13)	0.17751 (9)	0.0276 (3)
H24	1.1182	0.7418	0.1867	0.033*
C25	0.9594 (3)	0.86956 (13)	0.21587 (9)	0.0260 (3)
H25	1.0767	0.9221	0.2508	0.031*
C26	0.8384 (3)	0.56743 (14)	0.08535 (11)	0.0414 (4)
H26A	0.7230	0.5151	0.0976	0.062*
H26B	0.9802	0.5569	0.1048	0.062*
H26C	0.8275	0.5541	0.0272	0.062*
N2	0.8567 (2)	1.12308 (11)	0.22299 (8)	0.0285 (3)
O4	0.81390 (19)	1.05591 (9)	0.33850 (6)	0.0326 (3)
O5	0.49416 (18)	1.02921 (9)	0.23866 (7)	0.0345 (3)
O6	0.82296 (18)	1.32622 (9)	0.20231 (6)	0.0246 (2)
S2	0.72262 (6)	1.03181 (3)	0.25663 (2)	0.02444 (11)
H2N	0.981 (3)	1.1520 (16)	0.2453 (11)	0.040 (6)*
H6O	0.751 (4)	1.3754 (19)	0.2141 (13)	0.061 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0245 (8)	0.0189 (7)	0.0237 (7)	0.0036 (6)	−0.0012 (6)	0.0050 (6)
C2	0.0177 (7)	0.0233 (7)	0.0270 (8)	0.0037 (6)	0.0014 (6)	0.0080 (6)
C3	0.0286 (9)	0.0345 (9)	0.0307 (8)	0.0111 (7)	−0.0005 (7)	0.0128 (7)
C4	0.0389 (10)	0.0442 (10)	0.0277 (8)	0.0158 (8)	0.0068 (7)	0.0177 (7)
C5	0.0375 (10)	0.0382 (9)	0.0257 (8)	0.0127 (8)	0.0057 (7)	0.0068 (7)
C6	0.0293 (9)	0.0256 (8)	0.0260 (8)	0.0117 (7)	0.0049 (6)	0.0054 (6)
C7	0.0221 (8)	0.0212 (7)	0.0237 (7)	0.0071 (6)	0.0046 (6)	0.0099 (6)
C8	0.0237 (8)	0.0256 (8)	0.0240 (7)	0.0051 (6)	0.0049 (6)	0.0099 (6)
C9	0.0337 (9)	0.0227 (8)	0.0275 (8)	0.0039 (7)	0.0026 (7)	0.0080 (6)
C10	0.0394 (10)	0.0282 (8)	0.0226 (8)	0.0152 (7)	0.0027 (7)	0.0080 (6)
C11	0.0286 (9)	0.0383 (9)	0.0344 (9)	0.0170 (7)	0.0114 (7)	0.0164 (7)
C12	0.0235 (8)	0.0280 (8)	0.0382 (9)	0.0074 (6)	0.0069 (7)	0.0153 (7)
C13	0.0564 (13)	0.0389 (10)	0.0413 (11)	0.0240 (9)	0.0051 (9)	0.0021 (8)
N1	0.0210 (7)	0.0224 (6)	0.0285 (7)	−0.0005 (5)	−0.0031 (5)	0.0106 (5)
O1	0.0401 (7)	0.0300 (6)	0.0254 (6)	0.0060 (5)	0.0061 (5)	0.0087 (5)
O2	0.0210 (6)	0.0244 (6)	0.0502 (7)	0.0075 (5)	0.0079 (5)	0.0073 (5)
O3	0.0234 (6)	0.0204 (5)	0.0322 (6)	0.0070 (5)	0.0023 (5)	0.0026 (4)
S1	0.0216 (2)	0.01999 (19)	0.0284 (2)	0.00532 (14)	0.00508 (15)	0.00776 (15)
C14	0.0291 (8)	0.0184 (7)	0.0274 (8)	0.0021 (6)	−0.0020 (6)	0.0051 (6)
C15	0.0173 (7)	0.0232 (7)	0.0245 (7)	0.0023 (6)	0.0009 (6)	0.0069 (6)
C16	0.0258 (8)	0.0306 (8)	0.0256 (8)	0.0063 (7)	−0.0013 (6)	0.0084 (6)
C17	0.0329 (9)	0.0383 (9)	0.0236 (8)	0.0084 (7)	0.0055 (6)	0.0106 (7)
C18	0.0422 (11)	0.0415 (10)	0.0282 (9)	0.0140 (8)	0.0095 (8)	0.0022 (7)
C19	0.0356 (10)	0.0278 (8)	0.0343 (9)	0.0167 (7)	0.0075 (7)	0.0045 (7)
C20	0.0232 (8)	0.0187 (7)	0.0243 (7)	0.0055 (6)	0.0056 (6)	0.0085 (6)
C21	0.0230 (8)	0.0252 (8)	0.0289 (8)	0.0071 (6)	0.0026 (6)	0.0090 (6)
C22	0.0328 (9)	0.0240 (8)	0.0274 (8)	0.0046 (7)	0.0011 (7)	0.0048 (6)
C23	0.0380 (9)	0.0250 (8)	0.0261 (8)	0.0130 (7)	0.0150 (7)	0.0112 (6)
C24	0.0256 (8)	0.0324 (8)	0.0333 (8)	0.0140 (7)	0.0107 (6)	0.0167 (7)
C25	0.0219 (8)	0.0279 (8)	0.0302 (8)	0.0050 (6)	0.0033 (6)	0.0119 (6)
C26	0.0559 (13)	0.0276 (9)	0.0450 (11)	0.0177 (8)	0.0194 (9)	0.0092 (8)
N2	0.0258 (8)	0.0223 (7)	0.0366 (8)	−0.0015 (6)	−0.0052 (6)	0.0133 (6)
O4	0.0412 (7)	0.0254 (6)	0.0288 (6)	0.0038 (5)	0.0057 (5)	0.0059 (5)
O5	0.0235 (6)	0.0230 (6)	0.0539 (8)	0.0081 (5)	0.0060 (5)	0.0047 (5)
O6	0.0234 (6)	0.0209 (5)	0.0268 (6)	0.0066 (5)	0.0010 (4)	0.0023 (4)
S2	0.0242 (2)	0.01775 (18)	0.0308 (2)	0.00465 (15)	0.00403 (15)	0.00618 (15)

C1—N1	1.472 (2)	C14—N2	1.4690 (19)
C1—C2	1.528 (2)	C14—C15	1.528 (2)
C1—C6	1.529 (2)	C14—C19	1.532 (2)
C1—H1	1.0000	C14—H14	1.0000
C2—O3	1.4325 (17)	C15—O6	1.4316 (17)
C2—C3	1.525 (2)	C15—C16	1.526 (2)
C2—H2	1.0000	C15—H15	1.0000
C3—C4	1.531 (2)	C16—C17	1.530 (2)
C3—H3A	0.9900	C16—H16A	0.9900
C3—H3B	0.9900	C16—H16B	0.9900
C4—C5	1.522 (2)	C17—C18	1.522 (2)
C4—H4A	0.9900	C17—H17A	0.9900
C4—H4B	0.9900	C17—H17B	0.9900
C5—C6	1.530 (2)	C18—C19	1.528 (2)
C5—H5A	0.9900	C18—H18A	0.9900
C5—H5B	0.9900	C18—H18B	0.9900
C6—H6A	0.9900	C19—H19A	0.9900
C6—H6B	0.9900	C19—H19B	0.9900
C7—C8	1.390 (2)	C20—C21	1.385 (2)
C7—C12	1.393 (2)	C20—C25	1.389 (2)
C7—S1	1.7674 (14)	C20—S2	1.7665 (14)
C8—C9	1.387 (2)	C21—C22	1.391 (2)
C8—H8	0.9500	C21—H21	0.9500
C9—C10	1.393 (2)	C22—C23	1.392 (2)
C9—H9	0.9500	C22—H22	0.9500
C10—C11	1.386 (2)	C23—C24	1.388 (2)
C10—C13	1.507 (2)	C23—C26	1.507 (2)
C11—C12	1.384 (2)	C24—C25	1.387 (2)
C11—H11	0.9500	C24—H24	0.9500
C12—H12	0.9500	C25—H25	0.9500
C13—H13A	0.9800	C26—H26A	0.9800
C13—H13B	0.9800	C26—H26B	0.9800
C13—H13C	0.9800	C26—H26C	0.9800
N1—S1	1.5975 (13)	N2—S2	1.5982 (13)
N1—H1N	0.83 (2)	N2—H2N	0.82 (2)
O1—S1	1.4322 (11)	O4—S2	1.4343 (12)
O2—S1	1.4461 (11)	O5—S2	1.4452 (12)
O3—H3O	0.83 (2)	O6—H6O	0.83 (2)
N1—C1—C2	110.49 (11)	N2—C14—C15	110.28 (12)
N1—C1—C6	110.35 (12)	N2—C14—C19	109.93 (13)
C2—C1—C6	111.65 (12)	C15—C14—C19	112.15 (12)
N1—C1—H1	108.1	N2—C14—H14	108.1
C2—C1—H1	108.1	C15—C14—H14	108.1
C6—C1—H1	108.1	C19—C14—H14	108.1
O3—C2—C3	110.68 (12)	O6—C15—C16	110.75 (12)
O3—C2—C1	106.45 (11)	O6—C15—C14	107.06 (11)
C3—C2—C1	110.94 (12)	C16—C15—C14	110.71 (12)
O3—C2—H2	109.6	O6—C15—H15	109.4
C3—C2—H2	109.6	C16—C15—H15	109.4
C1—C2—H2	109.6	C14—C15—H15	109.4
C2—C3—C4	111.59 (13)	C15—C16—C17	111.19 (13)
C2—C3—H3A	109.3	C15—C16—H16A	109.4
C4—C3—H3A	109.3	C17—C16—H16A	109.4
C2—C3—H3B	109.3	C15—C16—H16B	109.4
C4—C3—H3B	109.3	C17—C16—H16B	109.4
H3A—C3—H3B	108.0	H16A—C16—H16B	108.0
C5—C4—C3	110.62 (14)	C18—C17—C16	110.11 (14)
C5—C4—H4A	109.5	C18—C17—H17A	109.6
C3—C4—H4A	109.5	C16—C17—H17A	109.6
C5—C4—H4B	109.5	C18—C17—H17B	109.6
C3—C4—H4B	109.5	C16—C17—H17B	109.6
H4A—C4—H4B	108.1	H17A—C17—H17B	108.2
C4—C5—C6	111.54 (13)	C17—C18—C19	110.83 (13)
C4—C5—H5A	109.3	C17—C18—H18A	109.5
C6—C5—H5A	109.3	C19—C18—H18A	109.5
C4—C5—H5B	109.3	C17—C18—H18B	109.5
C6—C5—H5B	109.3	C19—C18—H18B	109.5
H5A—C5—H5B	108.0	H18A—C18—H18B	108.1
C1—C6—C5	110.98 (13)	C18—C19—C14	110.71 (14)
C1—C6—H6A	109.4	C18—C19—H19A	109.5
C5—C6—H6A	109.4	C14—C19—H19A	109.5
C1—C6—H6B	109.4	C18—C19—H19B	109.5
C5—C6—H6B	109.4	C14—C19—H19B	109.5
H6A—C6—H6B	108.0	H19A—C19—H19B	108.1
C8—C7—C12	120.34 (14)	C21—C20—C25	120.81 (14)
C8—C7—S1	119.33 (11)	C21—C20—S2	119.75 (11)
C12—C7—S1	120.29 (11)	C25—C20—S2	119.36 (11)
C9—C8—C7	119.46 (14)	C20—C21—C22	119.29 (14)
C9—C8—H8	120.3	C20—C21—H21	120.4
C7—C8—H8	120.3	C22—C21—H21	120.4
C8—C9—C10	121.16 (15)	C21—C22—C23	120.93 (15)
C8—C9—H9	119.4	C21—C22—H22	119.5
C10—C9—H9	119.4	C23—C22—H22	119.5
C11—C10—C9	118.17 (14)	C24—C23—C22	118.55 (14)
C11—C10—C13	120.69 (16)	C24—C23—C26	121.60 (15)
C9—C10—C13	121.13 (16)	C22—C23—C26	119.84 (16)
C12—C11—C10	121.93 (15)	C25—C24—C23	121.41 (14)
C12—C11—H11	119.0	C25—C24—H24	119.3
C10—C11—H11	119.0	C23—C24—H24	119.3
C11—C12—C7	118.92 (15)	C24—C25—C20	119.00 (14)
C11—C12—H12	120.5	C24—C25—H25	120.5
C7—C12—H12	120.5	C20—C25—H25	120.5
C10—C13—H13A	109.5	C23—C26—H26A	109.5
C10—C13—H13B	109.5	C23—C26—H26B	109.5
H13A—C13—H13B	109.5	H26A—C26—H26B	109.5
C10—C13—H13C	109.5	C23—C26—H26C	109.5
H13A—C13—H13C	109.5	H26A—C26—H26C	109.5
H13B—C13—H13C	109.5	H26B—C26—H26C	109.5
C1—N1—S1	122.50 (10)	C14—N2—S2	122.76 (11)
C1—N1—H1N	119.7 (13)	C14—N2—H2N	117.8 (13)
S1—N1—H1N	113.8 (13)	S2—N2—H2N	116.7 (13)
C2—O3—H3O	107.3 (15)	C15—O6—H6O	107.3 (16)
O1—S1—O2	118.31 (7)	O4—S2—O5	119.25 (7)
O1—S1—N1	107.26 (7)	O4—S2—N2	106.51 (7)
O2—S1—N1	108.38 (7)	O5—S2—N2	107.95 (7)
O1—S1—C7	109.32 (7)	O4—S2—C20	108.22 (7)
O2—S1—C7	105.55 (7)	O5—S2—C20	105.34 (7)
N1—S1—C7	107.60 (7)	N2—S2—C20	109.34 (7)
N1—C1—C2—O3	−57.65 (14)	N2—C14—C15—O6	56.00 (15)
C6—C1—C2—O3	65.57 (15)	C19—C14—C15—O6	−66.87 (15)
N1—C1—C2—C3	−178.14 (12)	N2—C14—C15—C16	176.81 (12)
C6—C1—C2—C3	−54.92 (16)	C19—C14—C15—C16	53.94 (16)
O3—C2—C3—C4	−62.41 (17)	O6—C15—C16—C17	62.91 (16)
C1—C2—C3—C4	55.53 (17)	C14—C15—C16—C17	−55.68 (16)
C2—C3—C4—C5	−56.05 (19)	C15—C16—C17—C18	58.13 (18)
C3—C4—C5—C6	55.88 (19)	C16—C17—C18—C19	−58.33 (19)
N1—C1—C6—C5	178.09 (12)	C17—C18—C19—C14	56.40 (19)
C2—C1—C6—C5	54.80 (16)	N2—C14—C19—C18	−177.42 (13)
C4—C5—C6—C1	−55.44 (18)	C15—C14—C19—C18	−54.35 (17)
C12—C7—C8—C9	0.9 (2)	C25—C20—C21—C22	1.2 (2)
S1—C7—C8—C9	178.53 (11)	S2—C20—C21—C22	−175.50 (11)
C7—C8—C9—C10	0.2 (2)	C20—C21—C22—C23	−0.1 (2)
C8—C9—C10—C11	−0.8 (2)	C21—C22—C23—C24	−0.7 (2)
C8—C9—C10—C13	−179.95 (15)	C21—C22—C23—C26	178.69 (14)
C9—C10—C11—C12	0.2 (2)	C22—C23—C24—C25	0.6 (2)
C13—C10—C11—C12	179.39 (15)	C26—C23—C24—C25	−178.82 (14)
C10—C11—C12—C7	0.9 (2)	C23—C24—C25—C20	0.4 (2)
C8—C7—C12—C11	−1.5 (2)	C21—C20—C25—C24	−1.3 (2)
S1—C7—C12—C11	−179.05 (12)	S2—C20—C25—C24	175.38 (11)
C2—C1—N1—S1	−103.58 (13)	C15—C14—N2—S2	102.29 (14)
C6—C1—N1—S1	132.45 (12)	C19—C14—N2—S2	−133.55 (12)
C1—N1—S1—O1	175.08 (11)	C14—N2—S2—O4	−174.30 (12)
C1—N1—S1—O2	46.28 (13)	C14—N2—S2—O5	−45.13 (14)
C1—N1—S1—C7	−67.40 (13)	C14—N2—S2—C20	68.98 (14)
C8—C7—S1—O1	−95.15 (13)	C21—C20—S2—O4	134.13 (12)
C12—C7—S1—O1	82.45 (13)	C25—C20—S2—O4	−42.57 (13)
C8—C7—S1—O2	33.11 (14)	C21—C20—S2—O5	5.55 (14)
C12—C7—S1—O2	−149.29 (12)	C25—C20—S2—O5	−171.15 (11)
C8—C7—S1—N1	148.68 (12)	C21—C20—S2—N2	−110.23 (12)
C12—C7—S1—N1	−33.72 (14)	C25—C20—S2—N2	73.07 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6i	0.83 (2)	2.00 (2)	2.8255 (17)	175.0 (18)
N2—H2N···O3ii	0.82 (2)	2.00 (2)	2.8155 (18)	173.1 (19)
O3—H3O···O5iii	0.83 (2)	1.93 (2)	2.7489 (15)	171 (2)
O6—H6O···O2iv	0.83 (2)	1.98 (2)	2.8001 (15)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O6i	0.83 (2)	2.00 (2)	2.8255 (17)	175.0 (18)
N2—H2N⋯O3ii	0.82 (2)	2.00 (2)	2.8155 (18)	173.1 (19)
O3—H3O⋯O5iii	0.83 (2)	1.93 (2)	2.7489 (15)	171 (2)
O6—H6O⋯O2iv	0.83 (2)	1.98 (2)	2.8001 (15)	169 (2)

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