2-Benzene-sulfonamido-3-methyl-butyric acid.

In the crystal structure of the title compound, C(11)H(15)NO(4)S, two independent mol-ecules are present per asymmetric unit; they are dimerized through O-H⋯O hydrogen bonds between their carb-oxy groups to generate R(2) (2)(8) loops. An intra-molecular N-H⋯O link in one of the mol-ecules closes an S(5) ring. The dimers are linked by N-H⋯O and C-H⋯O hydrogen bonds to form a three-dimensional network. The C atoms of the isopropyl group of one of the mol-ecules are disordered over two orientations in a 3:1 ratio.

Related literature

For biological studies of sulfonamides, see: Nalam et al. (2007 ▶). For related structures, see: Khan et al. (2011 ▶); Arshad et al. (2012 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H15NO4S

M = 257.30

Monoclinic,

a = 5.4954 (3) Å

b = 15.5097 (10) Å

c = 15.5106 (9) Å

β = 94.043 (3)°

V = 1318.71 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.37 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.914, T max = 0.957

9573 measured reflections

4203 independent reflections

3803 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.093

S = 1.05

4203 reflections

335 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1785 Friedel pairs

Flack parameter: 0.00 (6)

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 X-SEED (Barbour, 2001 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812034393/hb6922sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034393/hb6922Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034393/hb6922Isup3.cml

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

C11H15NO4S	F(000) = 544
Mr = 257.30	Dx = 1.296 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4554 reflections
a = 5.4954 (3) Å	θ = 2.6–24.4°
b = 15.5097 (10) Å	µ = 0.25 mm−1
c = 15.5106 (9) Å	T = 296 K
β = 94.043 (3)°	Prismatic, colorless
V = 1318.71 (14) Å3	0.37 × 0.22 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4203 independent reflections
Radiation source: fine-focus sealed tube	3803 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −5→6
Tmin = 0.914, Tmax = 0.957	k = −15→18
9573 measured reflections	l = −18→18

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.036	w = 1/[σ2(Fo2) + (0.0543P)2 + 0.0931P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.093	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.18 e Å−3
4203 reflections	Δρmin = −0.18 e Å−3
335 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
7 restraints	Extinction coefficient: 0.0039 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1785 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.00 (6)

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)
S1	0.01018 (13)	0.47881 (5)	0.94705 (4)	0.0526 (2)
S2	0.63466 (11)	0.90716 (5)	0.55510 (4)	0.04379 (18)
O1	−0.2265 (4)	0.50382 (18)	0.97036 (13)	0.0746 (7)
O2	0.1285 (5)	0.40489 (17)	0.98428 (14)	0.0812 (7)
O3	0.3451 (4)	0.64351 (16)	0.82551 (15)	0.0762 (7)
O4	0.0009 (5)	0.7191 (2)	0.82050 (16)	0.0896 (9)
O5	0.4720 (4)	0.94893 (15)	0.49394 (12)	0.0615 (6)
O6	0.8908 (3)	0.91930 (15)	0.55236 (12)	0.0583 (5)
O7	0.0874 (3)	0.74580 (16)	0.65554 (14)	0.0683 (6)
O8	0.4671 (4)	0.69767 (18)	0.67244 (14)	0.0713 (7)
N1	0.1901 (4)	0.55941 (18)	0.97225 (14)	0.0519 (6)
N2	0.5961 (4)	0.80431 (17)	0.54293 (14)	0.0470 (6)
C1	−0.0023 (4)	0.4673 (2)	0.83346 (15)	0.0478 (7)
C2	−0.1899 (5)	0.5045 (2)	0.78370 (19)	0.0642 (9)
H2	−0.3146	0.5332	0.8094	0.077*
C3	−0.1909 (7)	0.4988 (3)	0.6954 (2)	0.0783 (11)
H3	−0.3168	0.5243	0.6611	0.094*
C4	−0.0131 (7)	0.4572 (3)	0.6580 (2)	0.0799 (11)
H4	−0.0170	0.4533	0.5980	0.096*
C5	0.1747 (7)	0.4201 (3)	0.7076 (2)	0.0877 (13)
H5	0.2987	0.3916	0.6814	0.105*
C6	0.1802 (6)	0.4251 (3)	0.7962 (2)	0.0721 (10)
H6	0.3070	0.4000	0.8303	0.087*
C7	0.1146 (7)	0.6464 (2)	0.95050 (19)	0.0640 (8)
H7	−0.0636	0.6460	0.9511	0.077*
C8	0.1658 (6)	0.6696 (2)	0.8590 (2)	0.0598 (8)
C9A	0.2016 (11)	0.7179 (4)	1.0149 (3)	0.0846 (16)	0.75
H9A	0.1325	0.7736	0.9960	0.102*	0.75
C9B	0.336 (5)	0.6908 (11)	1.0186 (10)	0.0846 (16)	0.25
H9B	0.4889	0.6580	1.0183	0.102*	0.25
C10A	0.1194 (16)	0.6948 (6)	1.1039 (4)	0.1206 (18)	0.75
H10A	0.1968	0.6422	1.1235	0.181*	0.75
H10B	−0.0544	0.6874	1.1004	0.181*	0.75
H10C	0.1642	0.7403	1.1439	0.181*	0.75
C10B	0.252 (4)	0.699 (2)	1.1091 (11)	0.132 (8)	0.25
H10D	0.3754	0.7273	1.1455	0.198*	0.25
H10E	0.2248	0.6420	1.1317	0.198*	0.25
H10F	0.1035	0.7311	1.1075	0.198*	0.25
C11A	0.4800 (14)	0.7213 (6)	1.0175 (5)	0.1206 (18)	0.75
H11A	0.5307	0.7257	0.9597	0.181*	0.75
H11B	0.5466	0.6698	1.0441	0.181*	0.75
H11C	0.5375	0.7706	1.0504	0.181*	0.75
C11B	0.366 (4)	0.7811 (13)	0.9824 (12)	0.132 (8)	0.25
H11D	0.4428	0.8176	1.0264	0.198*	0.25
H11E	0.2083	0.8041	0.9643	0.198*	0.25
H11F	0.4648	0.7787	0.9339	0.198*	0.25
C12	0.5515 (5)	0.93452 (19)	0.65875 (17)	0.0517 (7)
C13	0.6936 (7)	0.9040 (3)	0.72930 (18)	0.0840 (11)
H13	0.8328	0.8715	0.7219	0.101*
C14	0.6242 (12)	0.9230 (4)	0.8109 (2)	0.1203 (18)
H14	0.7154	0.9018	0.8591	0.144*
C15	0.4279 (12)	0.9714 (5)	0.8216 (3)	0.135 (2)
H15	0.3843	0.9836	0.8771	0.162*
C16	0.2912 (8)	1.0028 (4)	0.7526 (4)	0.130 (2)
H16	0.1549	1.0364	0.7613	0.156*
C17	0.3527 (6)	0.9852 (3)	0.6681 (3)	0.0889 (12)
H17	0.2615	1.0073	0.6203	0.107*
C18	0.3522 (4)	0.76567 (19)	0.53994 (17)	0.0444 (6)
H18	0.2335	0.8099	0.5203	0.053*
C19	0.2898 (5)	0.7353 (2)	0.62866 (19)	0.0515 (7)
C20	0.3346 (5)	0.6908 (2)	0.4741 (2)	0.0617 (8)
H20	0.4612	0.6485	0.4915	0.074*
C21	0.3830 (8)	0.7240 (3)	0.3847 (2)	0.0929 (13)
H21A	0.3896	0.6763	0.3455	0.139*
H21B	0.5357	0.7543	0.3875	0.139*
H21C	0.2542	0.7624	0.3646	0.139*
C22	0.0909 (7)	0.6464 (3)	0.4729 (3)	0.1032 (15)
H22A	−0.0359	0.6867	0.4557	0.155*
H22B	0.0657	0.6249	0.5296	0.155*
H22C	0.0873	0.5993	0.4327	0.155*
H1N	0.329 (8)	0.544 (4)	0.967 (3)	0.124*
H2N	0.701 (8)	0.775 (4)	0.569 (3)	0.124*
H4O	0.016 (10)	0.736 (4)	0.7683 (15)	0.155*
H8O	0.423 (9)	0.676 (4)	0.719 (2)	0.155*

	U11	U22	U33	U12	U13	U23
S1	0.0641 (4)	0.0565 (5)	0.0374 (3)	−0.0096 (3)	0.0055 (3)	0.0090 (3)
S2	0.0456 (3)	0.0506 (4)	0.0350 (3)	−0.0056 (3)	0.0010 (2)	0.0099 (3)
O1	0.0674 (13)	0.110 (2)	0.0498 (11)	−0.0205 (12)	0.0258 (10)	−0.0023 (12)
O2	0.1254 (19)	0.0546 (14)	0.0609 (12)	−0.0055 (15)	−0.0131 (12)	0.0208 (12)
O3	0.0810 (14)	0.0791 (18)	0.0719 (14)	0.0184 (13)	0.0298 (12)	0.0299 (13)
O4	0.0912 (17)	0.104 (2)	0.0765 (16)	0.0295 (15)	0.0289 (14)	0.0358 (16)
O5	0.0675 (12)	0.0630 (14)	0.0517 (11)	−0.0038 (10)	−0.0127 (9)	0.0186 (9)
O6	0.0503 (10)	0.0710 (16)	0.0540 (10)	−0.0132 (10)	0.0062 (8)	0.0129 (10)
O7	0.0496 (11)	0.0854 (17)	0.0726 (14)	0.0144 (10)	0.0227 (10)	0.0315 (12)
O8	0.0566 (12)	0.0935 (19)	0.0656 (14)	0.0184 (12)	0.0166 (10)	0.0356 (13)
N1	0.0609 (13)	0.0558 (17)	0.0387 (11)	−0.0016 (12)	0.0024 (10)	0.0051 (11)
N2	0.0405 (11)	0.0574 (17)	0.0440 (12)	−0.0009 (10)	0.0088 (9)	0.0049 (11)
C1	0.0488 (14)	0.0562 (19)	0.0386 (13)	−0.0048 (13)	0.0049 (11)	−0.0002 (13)
C2	0.0537 (16)	0.091 (3)	0.0480 (15)	0.0123 (15)	0.0015 (13)	−0.0100 (15)
C3	0.082 (2)	0.105 (3)	0.0460 (16)	0.012 (2)	−0.0087 (15)	−0.0079 (18)
C4	0.091 (2)	0.104 (3)	0.0449 (16)	−0.009 (2)	0.0090 (17)	−0.0220 (18)
C5	0.083 (2)	0.111 (4)	0.071 (2)	0.014 (2)	0.0245 (19)	−0.028 (2)
C6	0.0671 (18)	0.084 (3)	0.0648 (19)	0.0208 (18)	0.0004 (15)	−0.0091 (17)
C7	0.084 (2)	0.055 (2)	0.0549 (17)	−0.0038 (16)	0.0198 (15)	0.0013 (15)
C8	0.0667 (19)	0.056 (2)	0.0592 (17)	0.0038 (15)	0.0203 (15)	0.0137 (15)
C9A	0.118 (5)	0.060 (4)	0.076 (3)	0.017 (3)	0.008 (3)	−0.017 (3)
C9B	0.118 (5)	0.060 (4)	0.076 (3)	0.017 (3)	0.008 (3)	−0.017 (3)
C10A	0.145 (5)	0.124 (5)	0.092 (3)	−0.026 (4)	0.001 (3)	−0.035 (3)
C10B	0.138 (15)	0.163 (17)	0.094 (9)	−0.098 (14)	0.000 (9)	−0.032 (10)
C11A	0.145 (5)	0.124 (5)	0.092 (3)	−0.026 (4)	0.001 (3)	−0.035 (3)
C11B	0.138 (15)	0.163 (17)	0.094 (9)	−0.098 (14)	0.000 (9)	−0.032 (10)
C12	0.0509 (15)	0.059 (2)	0.0456 (15)	−0.0092 (13)	0.0033 (12)	−0.0048 (13)
C13	0.111 (3)	0.100 (3)	0.0396 (15)	0.019 (3)	−0.0019 (16)	0.0004 (19)
C14	0.175 (5)	0.148 (5)	0.0382 (19)	−0.020 (4)	0.007 (2)	−0.016 (3)
C15	0.140 (4)	0.196 (7)	0.074 (3)	−0.052 (5)	0.044 (3)	−0.075 (4)
C16	0.076 (3)	0.196 (7)	0.122 (4)	−0.007 (3)	0.031 (3)	−0.090 (4)
C17	0.0591 (19)	0.120 (4)	0.086 (2)	0.007 (2)	−0.0036 (17)	−0.041 (3)
C18	0.0423 (13)	0.0456 (17)	0.0457 (14)	−0.0035 (12)	0.0057 (11)	0.0087 (12)
C19	0.0486 (15)	0.0491 (18)	0.0579 (17)	0.0040 (13)	0.0118 (13)	0.0099 (13)
C20	0.0570 (17)	0.055 (2)	0.072 (2)	0.0017 (15)	0.0021 (14)	−0.0047 (16)
C21	0.121 (3)	0.101 (4)	0.055 (2)	−0.006 (3)	−0.002 (2)	−0.023 (2)
C22	0.086 (3)	0.076 (3)	0.147 (4)	−0.022 (2)	0.004 (3)	−0.030 (3)

S1—O2	1.420 (3)	C9B—C11B	1.522 (10)
S1—O1	1.428 (2)	C9B—H9B	0.9800
S1—N1	1.624 (3)	C10A—H10A	0.9600
S1—C1	1.767 (2)	C10A—H10B	0.9600
S2—O5	1.414 (2)	C10A—H10C	0.9600
S2—O6	1.4239 (19)	C10B—H10D	0.9600
S2—N2	1.619 (3)	C10B—H10E	0.9600
S2—C12	1.754 (3)	C10B—H10F	0.9600
O3—C8	1.215 (4)	C11A—H11A	0.9600
O4—C8	1.300 (4)	C11A—H11B	0.9600
O4—H4O	0.859 (10)	C11A—H11C	0.9600
O7—C19	1.226 (3)	C11B—H11D	0.9600
O8—C19	1.288 (3)	C11B—H11E	0.9600
O8—H8O	0.849 (10)	C11B—H11F	0.9600
N1—C7	1.445 (4)	C12—C17	1.362 (5)
N1—H1N	0.81 (5)	C12—C13	1.382 (4)
N2—C18	1.466 (3)	C13—C14	1.379 (6)
N2—H2N	0.82 (5)	C13—H13	0.9300
C1—C6	1.359 (4)	C14—C15	1.334 (8)
C1—C2	1.371 (4)	C14—H14	0.9300
C2—C3	1.373 (4)	C15—C16	1.354 (8)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.338 (5)	C16—C17	1.403 (6)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.370 (5)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.516 (4)
C5—C6	1.375 (5)	C18—C20	1.545 (4)
C5—H5	0.9300	C18—H18	0.9800
C6—H6	0.9300	C20—C22	1.505 (5)
C7—C8	1.510 (4)	C20—C21	1.521 (5)
C7—C9A	1.545 (6)	C20—H20	0.9800
C7—C9B	1.70 (2)	C21—H21A	0.9600
C7—H7	0.9800	C21—H21B	0.9600
C9A—C10A	1.526 (7)	C21—H21C	0.9600
C9A—C11A	1.528 (7)	C22—H22A	0.9600
C9A—H9A	0.9800	C22—H22B	0.9600
C9B—C10B	1.513 (10)	C22—H22C	0.9600
O2—S1—O1	121.01 (16)	C10B—C9B—H9B	111.3
O2—S1—N1	105.66 (14)	C11B—C9B—H9B	111.3
O1—S1—N1	106.25 (15)	C7—C9B—H9B	111.3
O2—S1—C1	107.95 (15)	C9B—C10B—H10D	109.5
O1—S1—C1	107.93 (13)	C9B—C10B—H10E	109.5
N1—S1—C1	107.33 (12)	H10D—C10B—H10E	109.5
O5—S2—O6	119.94 (12)	C9B—C10B—H10F	109.5
O5—S2—N2	107.56 (13)	H10D—C10B—H10F	109.5
O6—S2—N2	104.39 (12)	H10E—C10B—H10F	109.5
O5—S2—C12	108.11 (14)	C9B—C11B—H11D	109.5
O6—S2—C12	108.50 (12)	C9B—C11B—H11E	109.5
N2—S2—C12	107.75 (13)	H11D—C11B—H11E	109.5
C8—O4—H4O	120 (4)	C9B—C11B—H11F	109.5
C19—O8—H8O	112 (4)	H11D—C11B—H11F	109.5
C7—N1—S1	120.2 (2)	H11E—C11B—H11F	109.5
C7—N1—H1N	121 (4)	C17—C12—C13	121.8 (3)
S1—N1—H1N	108 (4)	C17—C12—S2	120.0 (2)
C18—N2—S2	121.25 (18)	C13—C12—S2	118.3 (2)
C18—N2—H2N	114 (4)	C14—C13—C12	118.4 (4)
S2—N2—H2N	114 (4)	C14—C13—H13	120.8
C6—C1—C2	120.7 (3)	C12—C13—H13	120.8
C6—C1—S1	119.6 (2)	C15—C14—C13	120.8 (5)
C2—C1—S1	119.6 (2)	C15—C14—H14	119.6
C1—C2—C3	119.0 (3)	C13—C14—H14	119.6
C1—C2—H2	120.5	C14—C15—C16	120.8 (4)
C3—C2—H2	120.5	C14—C15—H15	119.6
C4—C3—C2	120.8 (3)	C16—C15—H15	119.6
C4—C3—H3	119.6	C15—C16—C17	120.8 (5)
C2—C3—H3	119.6	C15—C16—H16	119.6
C3—C4—C5	120.2 (3)	C17—C16—H16	119.6
C3—C4—H4	119.9	C12—C17—C16	117.3 (4)
C5—C4—H4	119.9	C12—C17—H17	121.3
C4—C5—C6	120.1 (3)	C16—C17—H17	121.3
C4—C5—H5	120.0	N2—C18—C19	111.3 (2)
C6—C5—H5	120.0	N2—C18—C20	110.1 (2)
C1—C6—C5	119.2 (3)	C19—C18—C20	111.0 (3)
C1—C6—H6	120.4	N2—C18—H18	108.1
C5—C6—H6	120.4	C19—C18—H18	108.1
N1—C7—C8	111.9 (3)	C20—C18—H18	108.1
N1—C7—C9A	116.7 (3)	O7—C19—O8	123.5 (3)
C8—C7—C9A	111.5 (3)	O7—C19—C18	122.4 (2)
N1—C7—C9B	93.0 (6)	O8—C19—C18	114.1 (2)
C8—C7—C9B	108.3 (6)	C22—C20—C21	110.9 (3)
C9A—C7—C9B	29.9 (6)	C22—C20—C18	111.5 (3)
N1—C7—H7	105.2	C21—C20—C18	109.9 (3)
C8—C7—H7	105.2	C22—C20—H20	108.1
C9A—C7—H7	105.2	C21—C20—H20	108.1
C9B—C7—H7	132.1	C18—C20—H20	108.1
O3—C8—O4	124.1 (3)	C20—C21—H21A	109.5
O3—C8—C7	122.2 (3)	C20—C21—H21B	109.5
O4—C8—C7	113.7 (3)	H21A—C21—H21B	109.5
C10A—C9A—C11A	110.1 (6)	C20—C21—H21C	109.5
C10A—C9A—C7	108.6 (5)	H21A—C21—H21C	109.5
C11A—C9A—C7	107.8 (5)	H21B—C21—H21C	109.5
C10A—C9A—H9A	110.1	C20—C22—H22A	109.5
C11A—C9A—H9A	110.1	C20—C22—H22B	109.5
C7—C9A—H9A	110.1	H22A—C22—H22B	109.5
C10B—C9B—C11B	108.4 (17)	C20—C22—H22C	109.5
C10B—C9B—C7	110.8 (17)	H22A—C22—H22C	109.5
C11B—C9B—C7	103.5 (14)	H22B—C22—H22C	109.5
O2—S1—N1—C7	−174.7 (2)	C8—C7—C9A—C11A	−66.9 (6)
O1—S1—N1—C7	−45.0 (2)	C9B—C7—C9A—C11A	22.7 (11)
C1—S1—N1—C7	70.3 (2)	N1—C7—C9B—C10B	−86.3 (18)
O5—S2—N2—C18	−50.0 (2)	C8—C7—C9B—C10B	159.4 (17)
O6—S2—N2—C18	−178.45 (19)	C9A—C7—C9B—C10B	58 (2)
C12—S2—N2—C18	66.3 (2)	N1—C7—C9B—C11B	157.6 (14)
O2—S1—C1—C6	−32.5 (3)	C8—C7—C9B—C11B	43.4 (15)
O1—S1—C1—C6	−164.8 (3)	C9A—C7—C9B—C11B	−58.1 (13)
N1—S1—C1—C6	81.0 (3)	O5—S2—C12—C17	2.4 (3)
O2—S1—C1—C2	150.6 (3)	O6—S2—C12—C17	134.0 (3)
O1—S1—C1—C2	18.3 (3)	N2—S2—C12—C17	−113.6 (3)
N1—S1—C1—C2	−95.9 (3)	O5—S2—C12—C13	−177.0 (3)
C6—C1—C2—C3	−0.2 (6)	O6—S2—C12—C13	−45.4 (3)
S1—C1—C2—C3	176.7 (3)	N2—S2—C12—C13	67.0 (3)
C1—C2—C3—C4	0.5 (6)	C17—C12—C13—C14	2.7 (7)
C2—C3—C4—C5	−0.7 (7)	S2—C12—C13—C14	−177.9 (4)
C3—C4—C5—C6	0.5 (7)	C12—C13—C14—C15	−1.6 (8)
C2—C1—C6—C5	0.0 (6)	C13—C14—C15—C16	0.3 (10)
S1—C1—C6—C5	−176.9 (3)	C14—C15—C16—C17	0.0 (10)
C4—C5—C6—C1	−0.2 (7)	C13—C12—C17—C16	−2.5 (6)
S1—N1—C7—C8	−84.3 (3)	S2—C12—C17—C16	178.1 (4)
S1—N1—C7—C9A	145.6 (3)	C15—C16—C17—C12	1.1 (8)
S1—N1—C7—C9B	164.6 (6)	S2—N2—C18—C19	−93.4 (2)
N1—C7—C8—O3	−35.6 (5)	S2—N2—C18—C20	143.0 (2)
C9A—C7—C8—O3	97.1 (5)	N2—C18—C19—O7	138.6 (3)
C9B—C7—C8—O3	65.4 (8)	C20—C18—C19—O7	−98.4 (3)
N1—C7—C8—O4	144.1 (3)	N2—C18—C19—O8	−41.7 (4)
C9A—C7—C8—O4	−83.3 (4)	C20—C18—C19—O8	81.3 (3)
C9B—C7—C8—O4	−114.9 (7)	N2—C18—C20—C22	176.9 (3)
N1—C7—C9A—C10A	−55.9 (7)	C19—C18—C20—C22	53.2 (4)
C8—C7—C9A—C10A	173.9 (5)	N2—C18—C20—C21	−59.7 (3)
C9B—C7—C9A—C10A	−96.6 (14)	C19—C18—C20—C21	176.6 (3)
N1—C7—C9A—C11A	63.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8O···O3	0.85 (1)	1.81 (1)	2.649 (3)	171 (6)
O4—H4O···O7	0.86 (1)	1.83 (2)	2.668 (3)	166 (6)
N1—H1N···O1i	0.81 (5)	2.52 (5)	3.322 (3)	172 (5)
N2—H2N···O7i	0.82 (5)	2.47 (5)	3.240 (3)	157 (5)
N2—H2N···O8	0.82 (5)	2.45 (5)	2.734 (3)	102 (4)
C2—H2···O3ii	0.93	2.56	3.440 (4)	158
C4—H4···O6iii	0.93	2.54	3.427 (4)	161
C14—H14···O2iv	0.93	2.52	3.378 (5)	154
C15—H15···O1v	0.93	2.60	3.521 (5)	173
C9A—H9A···O2v	0.98	2.52	3.421 (7)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8O⋯O3	0.85 (1)	1.81 (1)	2.649 (3)	171 (6)
O4—H4O⋯O7	0.86 (1)	1.83 (2)	2.668 (3)	166 (6)
N1—H1N⋯O1i	0.81 (5)	2.52 (5)	3.322 (3)	172 (5)
N2—H2N⋯O7i	0.82 (5)	2.47 (5)	3.240 (3)	157 (5)
N2—H2N⋯O8	0.82 (5)	2.45 (5)	2.734 (3)	102 (4)
C2—H2⋯O3ii	0.93	2.56	3.440 (4)	158
C4—H4⋯O6iii	0.93	2.54	3.427 (4)	161
C14—H14⋯O2iv	0.93	2.52	3.378 (5)	154
C15—H15⋯O1v	0.93	2.60	3.521 (5)	173
C9A—H9A⋯O2v	0.98	2.52	3.421 (7)	153

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