4-[(4-Methyl-benzene-sulfonamido)-meth-yl]cyclo-hexa-necarb-oxy-lic acid.

The title compound, C(15)H(21)NO(4)S, crystallized with two independent mol-ecules in the asymmetric unit in which the dihedral angles between the mean planes of the benzene and cyclo-hexane rings are 78.3 (2) and 67.6 (2)°. The substituents of the cyclo-hexyl rings are in equatorial orientations. In the crystal, both mol-ecules form R(2) (2)(6) carb-oxy-lic acid inversion dimers via pairs of O-H⋯O hydrogen bonds. Further N-H⋯O and C-H⋯O inter-actions generate a three-dimensional network.

Related literature

For background to tranexamic acid, see: Boylan et al. (1996 ▶); Nilsson (1980 ▶); Khan et al. (2002 ▶); Shah et al. (2010 ▶); Shahzadi et al. (2007 ▶); Svahn et al. (1986 ▶); Vávrová et al. (2005 ▶).

Experimental

Crystal data

C15H21NO4S

M = 311.40

Triclinic,

a = 6.0655 (5) Å

b = 10.3999 (9) Å

c = 26.468 (2) Å

α = 98.947 (3)°

β = 90.001 (4)°

γ = 104.880 (3)°

V = 1592.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.24 × 0.18 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

18232 measured reflections

7641 independent reflections

3536 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.227

S = 1.02

7641 reflections

394 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020083/hb5893sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020083/hb5893Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020083/hb5893Isup3.cml

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

C15H21NO4S	Z = 4
Mr = 311.40	F(000) = 664
Triclinic, P1	Dx = 1.299 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0655 (5) Å	Cell parameters from 2057 reflections
b = 10.3999 (9) Å	θ = 2.8–21.5°
c = 26.468 (2) Å	µ = 0.22 mm−1
α = 98.947 (3)°	T = 296 K
β = 90.001 (4)°	Plate, colourless
γ = 104.880 (3)°	0.24 × 0.18 × 0.07 mm
V = 1592.6 (2) Å3

Bruker APEXII CCD diffractometer	3536 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.059
graphite	θmax = 28.3°, θmin = 2.3°
φ and ω scans	h = −5→8
18232 measured reflections	k = −13→13
7641 independent reflections	l = −33→35

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.227	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.1014P)2] where P = (Fo2 + 2Fc2)/3
7641 reflections	(Δ/σ)max = 0.001
394 parameters	Δρmax = 0.53 e Å−3
5 restraints	Δρmin = −0.35 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.59294 (16)	0.36920 (10)	0.78560 (4)	0.0462 (3)
O1	0.4029 (4)	0.2571 (3)	0.78800 (10)	0.0609 (10)
O2	0.5563 (5)	0.4991 (3)	0.78533 (10)	0.0647 (11)
O3	1.2671 (7)	−0.0636 (4)	0.53183 (13)	0.1013 (17)
O4	1.4863 (7)	0.1415 (4)	0.54321 (14)	0.1083 (17)
N1	0.7227 (5)	0.3365 (3)	0.73371 (11)	0.0450 (11)
C1	1.2352 (11)	0.4191 (6)	0.96605 (19)	0.114 (3)
C2	1.0735 (9)	0.4061 (5)	0.92107 (17)	0.0733 (19)
C3	1.1413 (8)	0.4766 (6)	0.88168 (19)	0.093 (2)
C4	0.9963 (8)	0.4656 (5)	0.84050 (17)	0.0814 (19)
C5	0.7805 (6)	0.3824 (4)	0.83802 (13)	0.0442 (12)
C6	0.7115 (8)	0.3108 (4)	0.87682 (15)	0.0656 (17)
C7	0.8597 (10)	0.3241 (5)	0.91804 (17)	0.082 (2)
C8	0.7808 (7)	0.2069 (4)	0.72344 (14)	0.0562 (16)
C9	0.8747 (8)	0.1807 (4)	0.67113 (16)	0.0592 (17)
C10	1.0961 (9)	0.2721 (5)	0.6634 (2)	0.092 (2)
C11	1.1912 (10)	0.2368 (4)	0.61059 (19)	0.093 (2)
C12	1.2054 (9)	0.0906 (4)	0.60319 (17)	0.0717 (19)
C13	0.9806 (9)	−0.0001 (5)	0.60706 (19)	0.084 (2)
C14	0.8840 (10)	0.0355 (4)	0.65955 (18)	0.086 (2)
C15	1.3243 (9)	0.0523 (5)	0.55579 (17)	0.0653 (17)
S2	0.25305 (15)	0.71011 (9)	0.71862 (3)	0.0417 (3)
O5	0.1844 (5)	0.8290 (3)	0.71441 (10)	0.0600 (10)
O6	0.0813 (4)	0.5889 (3)	0.72280 (9)	0.0562 (9)
O7	1.3989 (6)	1.0912 (4)	0.95942 (13)	0.0918 (17)
O8	1.2587 (6)	0.8845 (3)	0.97377 (12)	0.0874 (12)
N2	0.4188 (5)	0.7396 (3)	0.76897 (10)	0.0416 (10)
C16	0.7982 (10)	0.5973 (6)	0.53281 (18)	0.110 (3)
C17	0.6599 (8)	0.6246 (5)	0.57895 (16)	0.0673 (17)
C18	0.6913 (8)	0.5789 (5)	0.62363 (18)	0.0771 (19)
C19	0.5698 (8)	0.6030 (5)	0.66593 (16)	0.0675 (17)
C20	0.4129 (6)	0.6759 (4)	0.66451 (13)	0.0429 (11)
C21	0.3779 (8)	0.7221 (4)	0.61988 (15)	0.0649 (17)
C22	0.4988 (10)	0.6941 (5)	0.57743 (17)	0.084 (2)
C23	0.6137 (6)	0.8615 (4)	0.77586 (13)	0.0464 (12)
C24	0.7819 (6)	0.8593 (4)	0.81700 (13)	0.0487 (12)
C25	0.6862 (7)	0.8384 (5)	0.86771 (15)	0.0705 (18)
C26	0.8735 (7)	0.8386 (5)	0.90713 (15)	0.0674 (16)
C27	1.0635 (7)	0.9679 (4)	0.91159 (15)	0.0641 (17)
C28	1.1607 (7)	0.9884 (5)	0.86120 (15)	0.0728 (19)
C29	0.9747 (7)	0.9873 (4)	0.82208 (14)	0.0597 (14)
C30	1.2480 (7)	0.9766 (5)	0.95100 (15)	0.0604 (16)
H1A	1.27680	0.51080	0.98320	0.1720*
H1B	1.36980	0.39360	0.95410	0.1720*
H1C	1.16170	0.36110	0.98940	0.1720*
H1N	0.831 (6)	0.408 (3)	0.7338 (16)	0.0790*
H3	1.28830	0.53290	0.88290	0.1110*
H4	1.04500	0.51480	0.81430	0.0980*
H4O	1.555 (6)	0.119 (3)	0.5172 (13)	0.0980*
H6	0.56550	0.25330	0.87550	0.0790*
H7	0.81110	0.27530	0.94440	0.0990*
H8A	0.64520	0.13520	0.72630	0.0670*
H8B	0.89300	0.20490	0.74920	0.0670*
H9	0.76490	0.19270	0.64630	0.0710*
H10A	1.20500	0.26930	0.68980	0.1100*
H10B	1.07990	0.36340	0.66720	0.1100*
H11A	1.09210	0.24870	0.58390	0.1120*
H11B	1.34170	0.29630	0.60840	0.1120*
H12	1.29950	0.08310	0.63210	0.0860*
H13A	0.99250	−0.09240	0.60260	0.1010*
H13B	0.87800	0.00720	0.58020	0.1010*
H14A	0.73120	−0.02250	0.66060	0.1030*
H14B	0.97800	0.01770	0.68590	0.1030*
H2N	0.442 (7)	0.666 (3)	0.7742 (15)	0.0720*
H7O	1.502 (6)	1.085 (5)	0.9778 (16)	0.0900*
H16A	0.71020	0.59260	0.50210	0.1650*
H16B	0.83640	0.51320	0.53270	0.1650*
H16C	0.93570	0.66870	0.53430	0.1650*
H18	0.79890	0.52980	0.62520	0.0930*
H19	0.59380	0.56980	0.69550	0.0810*
H21	0.27220	0.77250	0.61850	0.0780*
H22	0.46980	0.72310	0.54720	0.1010*
H23A	0.55680	0.94080	0.78460	0.0560*
H23B	0.69050	0.86770	0.74380	0.0560*
H24	0.84850	0.78400	0.80520	0.0580*
H25A	0.57100	0.75300	0.86400	0.0840*
H25B	0.61330	0.90940	0.88010	0.0840*
H26A	0.80760	0.83020	0.94020	0.0810*
H26B	0.93570	0.76190	0.89670	0.0810*
H27	0.99440	1.04250	0.92290	0.0770*
H28A	1.23410	0.91740	0.84910	0.0880*
H28B	1.27560	1.07390	0.86490	0.0880*
H29A	0.91360	1.06450	0.83240	0.0720*
H29B	1.04130	0.99550	0.78900	0.0720*

	U11	U22	U33	U12	U13	U23
S1	0.0430 (5)	0.0572 (6)	0.0446 (6)	0.0194 (5)	0.0095 (4)	0.0158 (4)
O1	0.0422 (15)	0.080 (2)	0.0572 (17)	0.0050 (14)	0.0078 (13)	0.0194 (14)
O2	0.079 (2)	0.0739 (19)	0.0602 (18)	0.0466 (17)	0.0198 (15)	0.0231 (15)
O3	0.116 (3)	0.082 (3)	0.093 (3)	0.018 (2)	0.046 (2)	−0.012 (2)
O4	0.123 (3)	0.091 (3)	0.099 (3)	0.019 (2)	0.064 (3)	−0.006 (2)
N1	0.0477 (19)	0.051 (2)	0.0425 (17)	0.0195 (15)	0.0098 (15)	0.0149 (15)
C1	0.113 (5)	0.165 (6)	0.072 (4)	0.063 (4)	−0.031 (3)	−0.006 (3)
C2	0.074 (3)	0.095 (4)	0.054 (3)	0.039 (3)	−0.010 (2)	−0.007 (3)
C3	0.051 (3)	0.151 (5)	0.067 (3)	0.010 (3)	−0.007 (2)	0.018 (3)
C4	0.053 (3)	0.123 (4)	0.064 (3)	0.002 (3)	0.004 (2)	0.038 (3)
C5	0.045 (2)	0.049 (2)	0.041 (2)	0.0157 (18)	0.0083 (17)	0.0083 (17)
C6	0.071 (3)	0.064 (3)	0.056 (3)	−0.001 (2)	0.000 (2)	0.023 (2)
C7	0.105 (4)	0.089 (4)	0.053 (3)	0.018 (3)	−0.006 (3)	0.025 (3)
C8	0.073 (3)	0.057 (3)	0.047 (2)	0.025 (2)	0.012 (2)	0.0202 (19)
C9	0.068 (3)	0.058 (3)	0.060 (3)	0.027 (2)	0.023 (2)	0.017 (2)
C10	0.071 (3)	0.086 (4)	0.105 (4)	0.014 (3)	0.026 (3)	−0.016 (3)
C11	0.111 (4)	0.061 (3)	0.098 (4)	0.014 (3)	0.064 (4)	0.004 (3)
C12	0.082 (4)	0.073 (3)	0.065 (3)	0.033 (3)	0.022 (3)	0.004 (2)
C13	0.090 (4)	0.067 (3)	0.093 (4)	0.027 (3)	0.030 (3)	−0.002 (3)
C14	0.119 (5)	0.059 (3)	0.086 (4)	0.032 (3)	0.050 (3)	0.017 (3)
C15	0.075 (3)	0.069 (3)	0.058 (3)	0.029 (3)	0.020 (3)	0.011 (3)
S2	0.0352 (5)	0.0511 (6)	0.0402 (5)	0.0129 (4)	0.0003 (4)	0.0085 (4)
O5	0.0653 (18)	0.0715 (19)	0.0554 (17)	0.0386 (15)	−0.0008 (14)	0.0119 (14)
O6	0.0385 (14)	0.0642 (18)	0.0570 (16)	−0.0050 (13)	−0.0009 (12)	0.0134 (13)
O7	0.080 (3)	0.092 (3)	0.093 (3)	0.000 (2)	−0.045 (2)	0.0209 (19)
O8	0.077 (2)	0.094 (2)	0.085 (2)	−0.0004 (19)	−0.0317 (18)	0.0339 (19)
N2	0.0432 (17)	0.0455 (19)	0.0356 (16)	0.0095 (15)	−0.0033 (13)	0.0088 (14)
C16	0.086 (4)	0.163 (6)	0.064 (3)	0.018 (4)	0.027 (3)	−0.007 (3)
C17	0.053 (3)	0.086 (3)	0.050 (3)	0.003 (2)	0.005 (2)	−0.003 (2)
C18	0.062 (3)	0.105 (4)	0.071 (3)	0.038 (3)	0.010 (3)	0.007 (3)
C19	0.072 (3)	0.094 (3)	0.053 (3)	0.046 (3)	0.017 (2)	0.021 (2)
C20	0.0376 (19)	0.048 (2)	0.040 (2)	0.0055 (17)	−0.0024 (16)	0.0070 (17)
C21	0.077 (3)	0.080 (3)	0.049 (3)	0.035 (3)	0.007 (2)	0.020 (2)
C22	0.102 (4)	0.114 (4)	0.044 (3)	0.036 (3)	0.012 (3)	0.022 (3)
C23	0.047 (2)	0.053 (2)	0.037 (2)	0.0067 (18)	−0.0012 (16)	0.0109 (17)
C24	0.043 (2)	0.056 (2)	0.045 (2)	0.0076 (18)	−0.0065 (17)	0.0111 (18)
C25	0.047 (2)	0.103 (4)	0.054 (3)	0.003 (2)	0.000 (2)	0.018 (2)
C26	0.054 (3)	0.094 (3)	0.046 (2)	−0.004 (2)	−0.009 (2)	0.026 (2)
C27	0.057 (3)	0.076 (3)	0.051 (3)	0.003 (2)	−0.015 (2)	0.009 (2)
C28	0.052 (3)	0.098 (4)	0.057 (3)	−0.007 (2)	−0.003 (2)	0.023 (2)
C29	0.048 (2)	0.072 (3)	0.052 (2)	−0.003 (2)	−0.0085 (19)	0.020 (2)
C30	0.054 (3)	0.073 (3)	0.046 (2)	0.005 (2)	−0.005 (2)	0.004 (2)

S1—O1	1.423 (3)	C10—H10B	0.9700
S1—O2	1.425 (3)	C10—H10A	0.9700
S1—N1	1.617 (3)	C11—H11A	0.9700
S1—C5	1.760 (4)	C11—H11B	0.9700
S2—N2	1.611 (3)	C12—H12	0.9800
S2—O5	1.422 (3)	C13—H13A	0.9700
S2—O6	1.434 (3)	C13—H13B	0.9700
S2—C20	1.771 (4)	C14—H14B	0.9700
O3—C15	1.234 (6)	C14—H14A	0.9700
O4—C15	1.251 (7)	C16—C17	1.513 (7)
O4—H4O	0.84 (4)	C17—C18	1.372 (7)
O7—C30	1.290 (6)	C17—C22	1.360 (8)
O8—C30	1.223 (6)	C18—C19	1.366 (7)
O7—H7O	0.81 (4)	C19—C20	1.364 (6)
N1—C8	1.465 (5)	C20—C21	1.379 (5)
N1—H1N	0.86 (3)	C21—C22	1.376 (7)
N2—C23	1.482 (5)	C23—C24	1.499 (5)
N2—H2N	0.84 (3)	C24—C29	1.517 (6)
C1—C2	1.510 (8)	C24—C25	1.487 (5)
C2—C3	1.370 (7)	C25—C26	1.542 (6)
C2—C7	1.351 (8)	C26—C27	1.518 (6)
C3—C4	1.373 (7)	C27—C28	1.482 (6)
C4—C5	1.366 (6)	C27—C30	1.506 (6)
C5—C6	1.365 (5)	C28—C29	1.528 (6)
C6—C7	1.381 (7)	C16—H16A	0.9600
C8—C9	1.509 (6)	C16—H16B	0.9600
C9—C14	1.509 (6)	C16—H16C	0.9600
C9—C10	1.468 (7)	C18—H18	0.9300
C10—C11	1.540 (7)	C19—H19	0.9300
C11—C12	1.527 (6)	C21—H21	0.9300
C12—C15	1.498 (7)	C22—H22	0.9300
C12—C13	1.459 (7)	C23—H23A	0.9700
C13—C14	1.537 (7)	C23—H23B	0.9700
C1—H1A	0.9600	C24—H24	0.9800
C1—H1B	0.9600	C25—H25A	0.9700
C1—H1C	0.9600	C25—H25B	0.9700
C3—H3	0.9300	C26—H26A	0.9700
C4—H4	0.9300	C26—H26B	0.9700
C6—H6	0.9300	C27—H27	0.9800
C7—H7	0.9300	C28—H28A	0.9700
C8—H8B	0.9700	C28—H28B	0.9700
C8—H8A	0.9700	C29—H29A	0.9700
C9—H9	0.9800	C29—H29B	0.9700
O1—S1—O2	119.56 (18)	C14—C13—H13A	110.00
O1—S1—N1	107.94 (16)	C12—C13—H13A	110.00
O1—S1—C5	107.47 (18)	C12—C13—H13B	110.00
O2—S1—N1	105.84 (17)	C14—C13—H13B	110.00
O2—S1—C5	107.52 (18)	H13A—C13—H13B	108.00
N1—S1—C5	108.07 (17)	C13—C14—H14B	109.00
N2—S2—C20	108.08 (17)	H14A—C14—H14B	108.00
O5—S2—N2	108.46 (16)	C9—C14—H14B	109.00
O5—S2—C20	107.58 (18)	C13—C14—H14A	109.00
O5—S2—O6	118.87 (18)	C9—C14—H14A	109.00
O6—S2—C20	107.80 (17)	C16—C17—C18	121.1 (5)
O6—S2—N2	105.65 (15)	C16—C17—C22	121.2 (4)
C15—O4—H4O	117 (2)	C18—C17—C22	117.7 (4)
C30—O7—H7O	109 (4)	C17—C18—C19	122.2 (5)
S1—N1—C8	118.0 (2)	C18—C19—C20	119.7 (4)
S1—N1—H1N	104 (3)	S2—C20—C19	121.1 (3)
C8—N1—H1N	118 (2)	S2—C20—C21	119.9 (3)
S2—N2—C23	118.2 (2)	C19—C20—C21	119.0 (4)
S2—N2—H2N	108 (3)	C20—C21—C22	120.3 (4)
C23—N2—H2N	119 (3)	C17—C22—C21	121.1 (4)
C3—C2—C7	118.0 (5)	N2—C23—C24	112.1 (3)
C1—C2—C3	120.6 (5)	C25—C24—C29	110.7 (3)
C1—C2—C7	121.4 (5)	C23—C24—C29	109.0 (3)
C2—C3—C4	121.2 (5)	C23—C24—C25	115.8 (3)
C3—C4—C5	120.1 (4)	C24—C25—C26	111.5 (4)
S1—C5—C6	120.5 (3)	C25—C26—C27	110.6 (4)
C4—C5—C6	119.3 (4)	C26—C27—C28	111.3 (3)
S1—C5—C4	120.3 (3)	C26—C27—C30	113.2 (4)
C5—C6—C7	119.7 (4)	C28—C27—C30	111.1 (4)
C2—C7—C6	121.8 (4)	C27—C28—C29	110.9 (4)
N1—C8—C9	113.0 (3)	C24—C29—C28	112.0 (3)
C10—C9—C14	111.0 (4)	O7—C30—O8	121.4 (4)
C8—C9—C14	109.4 (4)	O7—C30—C27	114.5 (4)
C8—C9—C10	115.1 (4)	O8—C30—C27	124.2 (4)
C9—C10—C11	113.3 (4)	C17—C16—H16A	110.00
C10—C11—C12	109.2 (4)	C17—C16—H16B	110.00
C13—C12—C15	113.7 (4)	C17—C16—H16C	109.00
C11—C12—C15	113.0 (4)	H16A—C16—H16B	109.00
C11—C12—C13	110.5 (5)	H16A—C16—H16C	109.00
C12—C13—C14	110.3 (4)	H16B—C16—H16C	109.00
C9—C14—C13	113.0 (4)	C17—C18—H18	119.00
O4—C15—C12	116.8 (4)	C19—C18—H18	119.00
O3—C15—O4	122.6 (5)	C18—C19—H19	120.00
O3—C15—C12	120.5 (5)	C20—C19—H19	120.00
C2—C1—H1C	109.00	C20—C21—H21	120.00
H1A—C1—H1B	110.00	C22—C21—H21	120.00
H1A—C1—H1C	110.00	C17—C22—H22	119.00
H1B—C1—H1C	109.00	C21—C22—H22	119.00
C2—C1—H1B	109.00	N2—C23—H23A	109.00
C2—C1—H1A	109.00	N2—C23—H23B	109.00
C4—C3—H3	119.00	C24—C23—H23A	109.00
C2—C3—H3	119.00	C24—C23—H23B	109.00
C3—C4—H4	120.00	H23A—C23—H23B	108.00
C5—C4—H4	120.00	C23—C24—H24	107.00
C7—C6—H6	120.00	C25—C24—H24	107.00
C5—C6—H6	120.00	C29—C24—H24	107.00
C2—C7—H7	119.00	C24—C25—H25A	109.00
C6—C7—H7	119.00	C24—C25—H25B	109.00
H8A—C8—H8B	108.00	C26—C25—H25A	109.00
N1—C8—H8B	109.00	C26—C25—H25B	109.00
C9—C8—H8B	109.00	H25A—C25—H25B	108.00
N1—C8—H8A	109.00	C25—C26—H26A	109.00
C9—C8—H8A	109.00	C25—C26—H26B	110.00
C10—C9—H9	107.00	C27—C26—H26A	110.00
C14—C9—H9	107.00	C27—C26—H26B	110.00
C8—C9—H9	107.00	H26A—C26—H26B	108.00
C9—C10—H10A	109.00	C26—C27—H27	107.00
C9—C10—H10B	109.00	C28—C27—H27	107.00
C11—C10—H10A	109.00	C30—C27—H27	107.00
C11—C10—H10B	109.00	C27—C28—H28A	109.00
H10A—C10—H10B	108.00	C27—C28—H28B	109.00
C10—C11—H11B	110.00	C29—C28—H28A	109.00
C12—C11—H11B	110.00	C29—C28—H28B	110.00
C12—C11—H11A	110.00	H28A—C28—H28B	108.00
C10—C11—H11A	110.00	C24—C29—H29A	109.00
H11A—C11—H11B	108.00	C24—C29—H29B	109.00
C13—C12—H12	106.00	C28—C29—H29A	109.00
C15—C12—H12	106.00	C28—C29—H29B	109.00
C11—C12—H12	106.00	H29A—C29—H29B	108.00
O1—S1—N1—C8	−50.3 (3)	C9—C10—C11—C12	−55.7 (6)
O2—S1—N1—C8	−179.4 (3)	C10—C11—C12—C13	58.8 (5)
C5—S1—N1—C8	65.7 (3)	C10—C11—C12—C15	−172.5 (4)
O1—S1—C5—C4	168.2 (3)	C11—C12—C15—O3	−147.3 (5)
O1—S1—C5—C6	−12.5 (4)	C11—C12—C15—O4	35.0 (7)
O2—S1—C5—C4	−61.9 (4)	C13—C12—C15—O4	162.0 (5)
O2—S1—C5—C6	117.5 (4)	C15—C12—C13—C14	172.9 (4)
N1—S1—C5—C4	51.9 (4)	C13—C12—C15—O3	−20.3 (7)
N1—S1—C5—C6	−128.7 (3)	C11—C12—C13—C14	−58.8 (5)
O5—S2—C20—C21	−25.3 (4)	C12—C13—C14—C9	55.4 (6)
O6—S2—C20—C19	−75.4 (4)	C16—C17—C18—C19	179.5 (5)
O6—S2—C20—C21	104.0 (4)	C22—C17—C18—C19	−1.1 (8)
N2—S2—C20—C19	38.4 (4)	C16—C17—C22—C21	−178.1 (5)
N2—S2—C20—C21	−142.3 (3)	C18—C17—C22—C21	2.5 (8)
O5—S2—N2—C23	−50.6 (3)	C17—C18—C19—C20	−0.7 (8)
O6—S2—N2—C23	−179.1 (3)	C18—C19—C20—S2	−179.7 (4)
C20—S2—N2—C23	65.7 (3)	C18—C19—C20—C21	1.0 (7)
O5—S2—C20—C19	155.3 (4)	S2—C20—C21—C22	−179.0 (4)
S1—N1—C8—C9	172.9 (3)	C19—C20—C21—C22	0.4 (7)
S2—N2—C23—C24	−166.7 (2)	C20—C21—C22—C17	−2.2 (7)
C1—C2—C3—C4	179.9 (5)	N2—C23—C24—C25	−54.0 (5)
C7—C2—C3—C4	0.6 (8)	N2—C23—C24—C29	−179.6 (3)
C3—C2—C7—C6	−0.2 (8)	C23—C24—C25—C26	−179.7 (4)
C1—C2—C7—C6	−179.4 (5)	C29—C24—C25—C26	−55.0 (5)
C2—C3—C4—C5	−0.5 (8)	C23—C24—C29—C28	−176.6 (3)
C3—C4—C5—S1	179.4 (4)	C25—C24—C29—C28	55.0 (4)
C3—C4—C5—C6	0.0 (7)	C24—C25—C26—C27	55.8 (5)
S1—C5—C6—C7	−178.9 (4)	C25—C26—C27—C28	−56.1 (5)
C4—C5—C6—C7	0.4 (7)	C25—C26—C27—C30	177.9 (3)
C5—C6—C7—C2	−0.4 (8)	C26—C27—C28—C29	56.0 (5)
N1—C8—C9—C10	65.8 (5)	C30—C27—C28—C29	−176.9 (4)
N1—C8—C9—C14	−168.5 (4)	C26—C27—C30—O7	−173.0 (4)
C14—C9—C10—C11	52.0 (5)	C26—C27—C30—O8	7.0 (6)
C8—C9—C14—C13	−179.3 (4)	C28—C27—C30—O7	60.9 (5)
C8—C9—C10—C11	176.9 (4)	C28—C27—C30—O8	−119.1 (5)
C10—C9—C14—C13	−51.3 (6)	C27—C28—C29—C24	−55.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O3i	0.84 (4)	1.81 (4)	2.638 (6)	171 (4)
O7—H7O···O8ii	0.81 (4)	1.87 (4)	2.664 (5)	166 (5)
N1—H1N···O6iii	0.86 (3)	2.15 (3)	3.001 (4)	171 (4)
N2—H2N···O2	0.84 (3)	2.09 (4)	2.924 (4)	171 (4)
C10—H10B···O6iii	0.97	2.57	3.446 (6)	151
C19—H19···O2	0.93	2.59	3.490 (5)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O3i	0.84 (4)	1.81 (4)	2.638 (6)	171 (4)
O7—H7O⋯O8ii	0.81 (4)	1.87 (4)	2.664 (5)	166 (5)
N1—H1N⋯O6iii	0.86 (3)	2.15 (3)	3.001 (4)	171 (4)
N2—H2N⋯O2	0.84 (3)	2.09 (4)	2.924 (4)	171 (4)
C10—H10B⋯O6iii	0.97	2.57	3.446 (6)	151
C19—H19⋯O2	0.93	2.59	3.490 (5)	164

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