N-{4-[(3,4-Dimethyl-phen-yl)sulfamo-yl]phen-yl}acetamide.

Two independent mol-ecules comprise the asymmetric unit of the title compound, C(16)H(18)N(2)O(3)S. Small but significant twists about the (S)N-C and S-C bonds differentiate the mol-ecules but the most obvious difference is found in the relative orientation of the meta-methyl groups, which lie on opposite sides of the mol-ecules. Overall, both mol-ecules adopt a U shape but with significant twisting evident, particularly in the second independent mol-ecule [dihedral angles between benzene rings = 63.90 (13) and 35.78 (11)°]. In the crystal, N-H⋯O hydrogen bonds lead to supra-molecular chains with a tubular topology propagating in [100] and C-H⋯O contacts cross-link the chains.

Related literature

For background to the anti­microbial activity of sulfonamides, see: Korolkovas, (1988 ▶); Mandell & Sande (1992 ▶). For related structures, see: John et al. (2010a ▶,b ▶).

Experimental

Crystal data

C16H18N2O3S

M = 318.40

Triclinic,

a = 8.4317 (3) Å

b = 13.6142 (5) Å

c = 15.1796 (5) Å

α = 71.340 (1)°

β = 77.136 (1)°

γ = 81.089 (1)°

V = 1602.83 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.27 × 0.11 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.817, T max = 0.940

27476 measured reflections

7319 independent reflections

5632 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.152

S = 1.06

7319 reflections

415 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.39 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: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶) and Qmol (Gans & Shalloway, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536810029405/hb5572sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029405/hb5572Isup2.hkl

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

C16H18N2O3S	Z = 4
Mr = 318.40	F(000) = 672
Triclinic, P1	Dx = 1.319 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4317 (3) Å	Cell parameters from 9916 reflections
b = 13.6142 (5) Å	θ = 2.5–28.2°
c = 15.1796 (5) Å	µ = 0.22 mm−1
α = 71.340 (1)°	T = 293 K
β = 77.136 (1)°	Prism, light-orange
γ = 81.089 (1)°	0.27 × 0.11 × 0.08 mm
V = 1602.83 (10) Å3

Bruker APEXII CCD diffractometer	7319 independent reflections
Radiation source: fine-focus sealed tube	5632 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.817, Tmax = 0.940	k = −17→17
27476 measured reflections	l = −19→19

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.079P)2 + 0.545P] where P = (Fo2 + 2Fc2)/3
7319 reflections	(Δ/σ)max = 0.001
415 parameters	Δρmax = 0.34 e Å−3
4 restraints	Δρmin = −0.39 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.98322 (6)	0.29377 (4)	0.73537 (4)	0.04718 (16)
O1	1.1132 (2)	0.28964 (14)	0.65701 (12)	0.0646 (5)
O2	0.9185 (2)	0.20011 (12)	0.79683 (13)	0.0621 (4)
O3	0.2213 (2)	0.51502 (15)	0.64850 (14)	0.0716 (5)
N1	1.0577 (2)	0.34788 (15)	0.79690 (13)	0.0490 (4)
H1N	1.105 (3)	0.4029 (13)	0.7617 (15)	0.059*
N2	0.4537 (2)	0.59093 (14)	0.57736 (14)	0.0516 (5)
H2N	0.488 (3)	0.6506 (12)	0.5403 (15)	0.062*
C1	0.9606 (3)	0.36318 (18)	0.88249 (15)	0.0479 (5)
C2	0.9398 (4)	0.2785 (2)	0.96293 (18)	0.0641 (6)
H2	0.9835	0.2122	0.9603	0.077*
C3	0.8541 (4)	0.2932 (2)	1.04648 (19)	0.0732 (8)
H3	0.8399	0.2361	1.1003	0.088*
C4	0.7889 (3)	0.3900 (2)	1.05273 (18)	0.0638 (6)
C5	0.8081 (3)	0.4762 (2)	0.97240 (19)	0.0595 (6)
C6	0.8955 (3)	0.46140 (19)	0.88680 (17)	0.0540 (5)
H6	0.9097	0.5181	0.8326	0.065*
C7	0.6971 (5)	0.4053 (3)	1.1468 (2)	0.0939 (10)
H7A	0.6751	0.3387	1.1917	0.141*
H7B	0.5959	0.4470	1.1376	0.141*
H7C	0.7625	0.4397	1.1700	0.141*
C8	0.7413 (4)	0.5840 (2)	0.9746 (2)	0.0844 (9)
H8A	0.6241	0.5881	0.9881	0.127*
H8B	0.7773	0.6328	0.9143	0.127*
H8C	0.7796	0.6003	1.0228	0.127*
C9	0.8222 (2)	0.37923 (16)	0.69024 (14)	0.0417 (4)
C10	0.8574 (3)	0.47298 (17)	0.62245 (17)	0.0524 (5)
H10	0.9649	0.4899	0.6015	0.063*
C11	0.7335 (3)	0.54057 (17)	0.58647 (17)	0.0522 (5)
H11	0.7574	0.6033	0.5407	0.063*
C12	0.5724 (2)	0.51646 (16)	0.61760 (15)	0.0433 (4)
C13	0.5385 (3)	0.42172 (19)	0.68438 (18)	0.0591 (6)
H13	0.4314	0.4040	0.7048	0.071*
C14	0.6637 (3)	0.35388 (18)	0.72046 (17)	0.0546 (6)
H14	0.6407	0.2905	0.7656	0.065*
C15	0.2910 (2)	0.58790 (17)	0.59298 (15)	0.0462 (5)
C16	0.2010 (3)	0.6818 (2)	0.53545 (18)	0.0591 (6)
H16A	0.1901	0.6702	0.4780	0.089*
H16B	0.2607	0.7415	0.5204	0.089*
H16C	0.0945	0.6939	0.5712	0.089*
S2	0.43431 (5)	0.11151 (4)	0.58705 (3)	0.03881 (14)
O4	0.42248 (18)	0.20348 (12)	0.50888 (10)	0.0522 (4)
O5	0.57822 (16)	0.04038 (12)	0.58419 (10)	0.0478 (3)
O6	−0.0669 (2)	−0.28130 (14)	0.73484 (17)	0.0821 (6)
N3	0.4199 (2)	0.15276 (13)	0.67873 (12)	0.0430 (4)
H3N	0.3329 (19)	0.1964 (15)	0.6800 (16)	0.052*
N4	−0.1488 (2)	−0.11535 (14)	0.65969 (13)	0.0449 (4)
H4N	−0.2356 (19)	−0.0768 (16)	0.6428 (16)	0.054*
C17	0.4346 (2)	0.07454 (16)	0.76766 (14)	0.0419 (4)
C18	0.5893 (3)	0.03908 (17)	0.78749 (14)	0.0467 (5)
H18	0.6796	0.0685	0.7452	0.056*
C19	0.6119 (3)	−0.03979 (19)	0.86957 (16)	0.0563 (6)
C20	0.4745 (4)	−0.08221 (18)	0.93320 (16)	0.0610 (6)
C21	0.3204 (4)	−0.0419 (2)	0.91310 (17)	0.0626 (6)
H21	0.2288	−0.0678	0.9566	0.075*
C22	0.2991 (3)	0.03525 (19)	0.83092 (16)	0.0540 (5)
H22	0.1948	0.0603	0.8185	0.065*
C23	0.7826 (4)	−0.0759 (3)	0.8881 (2)	0.0831 (10)
H23A	0.7900	−0.0700	0.9484	0.125*
H23B	0.8586	−0.0334	0.8393	0.125*
H23C	0.8081	−0.1472	0.8883	0.125*
C24	0.4914 (5)	−0.1688 (2)	1.02311 (19)	0.0908 (11)
H24A	0.3848	−0.1860	1.0587	0.136*
H24B	0.5491	−0.1466	1.0602	0.136*
H24C	0.5509	−0.2290	1.0076	0.136*
C25	0.2646 (2)	0.04302 (15)	0.60532 (13)	0.0374 (4)
C26	0.1210 (2)	0.09493 (15)	0.57695 (14)	0.0401 (4)
H26	0.1155	0.1660	0.5456	0.048*
C27	−0.0130 (2)	0.04060 (15)	0.59549 (14)	0.0414 (4)
H27	−0.1093	0.0752	0.5763	0.050*
C28	−0.0064 (2)	−0.06551 (15)	0.64266 (13)	0.0375 (4)
C29	0.1378 (3)	−0.11701 (17)	0.67113 (16)	0.0481 (5)
H29	0.1436	−0.1880	0.7027	0.058*
C30	0.2719 (2)	−0.06227 (16)	0.65223 (16)	0.0479 (5)
H30	0.3684	−0.0966	0.6713	0.058*
C31	−0.1732 (3)	−0.21692 (17)	0.70512 (16)	0.0500 (5)
C32	−0.3442 (3)	−0.2432 (2)	0.7171 (2)	0.0676 (7)
H32A	−0.3471	−0.3174	0.7390	0.101*
H32B	−0.3802	−0.2160	0.6575	0.101*
H32C	−0.4150	−0.2130	0.7624	0.101*

	U11	U22	U33	U12	U13	U23
S1	0.0455 (3)	0.0374 (3)	0.0539 (3)	0.0065 (2)	−0.0116 (2)	−0.0101 (2)
O1	0.0577 (9)	0.0618 (11)	0.0668 (11)	0.0172 (8)	−0.0044 (8)	−0.0239 (9)
O2	0.0679 (10)	0.0357 (8)	0.0770 (11)	−0.0009 (7)	−0.0216 (9)	−0.0051 (8)
O3	0.0444 (8)	0.0658 (11)	0.0858 (13)	−0.0150 (8)	−0.0131 (8)	0.0089 (10)
N1	0.0439 (9)	0.0468 (10)	0.0514 (10)	−0.0044 (7)	−0.0128 (8)	−0.0049 (8)
N2	0.0404 (9)	0.0415 (10)	0.0610 (11)	−0.0075 (7)	−0.0141 (8)	0.0059 (8)
C1	0.0462 (11)	0.0495 (12)	0.0479 (11)	−0.0076 (9)	−0.0156 (9)	−0.0079 (9)
C2	0.0833 (18)	0.0505 (14)	0.0547 (14)	−0.0087 (12)	−0.0202 (12)	−0.0041 (11)
C3	0.102 (2)	0.0596 (17)	0.0513 (14)	−0.0204 (15)	−0.0161 (14)	0.0007 (12)
C4	0.0640 (15)	0.0708 (17)	0.0557 (14)	−0.0198 (12)	−0.0127 (11)	−0.0101 (12)
C5	0.0582 (13)	0.0540 (14)	0.0721 (16)	−0.0057 (11)	−0.0218 (12)	−0.0196 (12)
C6	0.0547 (12)	0.0493 (13)	0.0562 (13)	−0.0065 (10)	−0.0187 (10)	−0.0065 (10)
C7	0.104 (3)	0.111 (3)	0.0642 (18)	−0.030 (2)	0.0025 (17)	−0.0253 (18)
C8	0.101 (2)	0.0665 (19)	0.088 (2)	0.0055 (16)	−0.0203 (18)	−0.0299 (16)
C9	0.0418 (10)	0.0380 (10)	0.0428 (10)	0.0009 (8)	−0.0108 (8)	−0.0085 (8)
C10	0.0392 (10)	0.0464 (12)	0.0626 (14)	−0.0084 (9)	−0.0101 (9)	−0.0015 (10)
C11	0.0431 (11)	0.0416 (12)	0.0596 (13)	−0.0102 (9)	−0.0114 (9)	0.0061 (10)
C12	0.0384 (9)	0.0402 (11)	0.0469 (11)	−0.0039 (8)	−0.0107 (8)	−0.0047 (9)
C13	0.0392 (10)	0.0521 (13)	0.0684 (15)	−0.0094 (9)	−0.0076 (10)	0.0073 (11)
C14	0.0486 (11)	0.0432 (12)	0.0557 (13)	−0.0061 (9)	−0.0064 (10)	0.0063 (10)
C15	0.0397 (10)	0.0475 (12)	0.0509 (12)	−0.0060 (8)	−0.0108 (8)	−0.0111 (10)
C16	0.0473 (12)	0.0582 (14)	0.0693 (15)	0.0021 (10)	−0.0215 (11)	−0.0114 (12)
S2	0.0337 (2)	0.0399 (3)	0.0370 (3)	−0.00307 (18)	−0.00693 (17)	−0.0032 (2)
O4	0.0509 (8)	0.0477 (9)	0.0472 (8)	−0.0108 (6)	−0.0123 (6)	0.0059 (7)
O5	0.0347 (7)	0.0563 (9)	0.0480 (8)	0.0032 (6)	−0.0056 (6)	−0.0141 (7)
O6	0.0568 (10)	0.0438 (10)	0.1222 (17)	−0.0065 (8)	−0.0184 (10)	0.0100 (10)
N3	0.0425 (9)	0.0375 (9)	0.0483 (9)	0.0003 (7)	−0.0121 (7)	−0.0109 (7)
N4	0.0395 (8)	0.0405 (10)	0.0530 (10)	−0.0030 (7)	−0.0140 (7)	−0.0083 (8)
C17	0.0471 (10)	0.0400 (11)	0.0396 (10)	−0.0025 (8)	−0.0088 (8)	−0.0134 (8)
C18	0.0494 (11)	0.0511 (12)	0.0402 (10)	0.0029 (9)	−0.0105 (8)	−0.0165 (9)
C19	0.0755 (15)	0.0512 (13)	0.0453 (12)	0.0171 (11)	−0.0212 (11)	−0.0224 (10)
C20	0.102 (2)	0.0404 (12)	0.0401 (11)	−0.0001 (12)	−0.0145 (12)	−0.0133 (10)
C21	0.0804 (17)	0.0556 (14)	0.0489 (13)	−0.0188 (13)	−0.0002 (12)	−0.0134 (11)
C22	0.0533 (12)	0.0550 (13)	0.0534 (13)	−0.0089 (10)	−0.0069 (10)	−0.0157 (11)
C23	0.089 (2)	0.100 (2)	0.0619 (16)	0.0414 (18)	−0.0383 (15)	−0.0322 (16)
C24	0.160 (3)	0.0508 (16)	0.0530 (15)	0.0002 (18)	−0.0255 (18)	−0.0038 (13)
C25	0.0364 (9)	0.0375 (10)	0.0358 (9)	−0.0003 (7)	−0.0069 (7)	−0.0085 (8)
C26	0.0414 (9)	0.0333 (10)	0.0414 (10)	0.0004 (7)	−0.0111 (8)	−0.0048 (8)
C27	0.0369 (9)	0.0387 (10)	0.0462 (11)	0.0024 (7)	−0.0134 (8)	−0.0081 (8)
C28	0.0389 (9)	0.0382 (10)	0.0348 (9)	−0.0016 (7)	−0.0074 (7)	−0.0103 (8)
C29	0.0466 (11)	0.0351 (10)	0.0569 (12)	−0.0011 (8)	−0.0154 (9)	−0.0032 (9)
C30	0.0388 (10)	0.0400 (11)	0.0587 (13)	0.0042 (8)	−0.0162 (9)	−0.0048 (9)
C31	0.0481 (11)	0.0446 (12)	0.0527 (12)	−0.0085 (9)	−0.0062 (9)	−0.0081 (10)
C32	0.0576 (14)	0.0593 (15)	0.0813 (18)	−0.0187 (12)	−0.0171 (12)	−0.0057 (13)

S1—O2	1.4219 (17)	S2—O4	1.4315 (14)
S1—O1	1.4363 (17)	S2—O5	1.4322 (14)
S1—N1	1.629 (2)	S2—N3	1.6342 (18)
S1—C9	1.755 (2)	S2—C25	1.7510 (19)
O3—C15	1.210 (3)	O6—C31	1.208 (3)
N1—C1	1.431 (3)	N3—C17	1.444 (3)
N1—H1N	0.866 (10)	N3—H3N	0.870 (10)
N2—C15	1.344 (3)	N4—C31	1.358 (3)
N2—C12	1.402 (3)	N4—C28	1.404 (2)
N2—H2N	0.876 (10)	N4—H4N	0.870 (10)
C1—C6	1.381 (3)	C17—C22	1.374 (3)
C1—C2	1.385 (3)	C17—C18	1.382 (3)
C2—C3	1.371 (4)	C18—C19	1.388 (3)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.371 (4)	C19—C20	1.400 (4)
C3—H3	0.9300	C19—C23	1.505 (4)
C4—C5	1.394 (4)	C20—C21	1.390 (4)
C4—C7	1.525 (4)	C20—C24	1.509 (3)
C5—C6	1.402 (4)	C21—C22	1.376 (3)
C5—C8	1.497 (4)	C21—H21	0.9300
C6—H6	0.9300	C22—H22	0.9300
C7—H7A	0.9600	C23—H23A	0.9600
C7—H7B	0.9600	C23—H23B	0.9600
C7—H7C	0.9600	C23—H23C	0.9600
C8—H8A	0.9600	C24—H24A	0.9600
C8—H8B	0.9600	C24—H24B	0.9600
C8—H8C	0.9600	C24—H24C	0.9600
C9—C14	1.372 (3)	C25—C30	1.380 (3)
C9—C10	1.385 (3)	C25—C26	1.386 (3)
C10—C11	1.368 (3)	C26—C27	1.374 (3)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.389 (3)	C27—C28	1.391 (3)
C11—H11	0.9300	C27—H27	0.9300
C12—C13	1.386 (3)	C28—C29	1.390 (3)
C13—C14	1.378 (3)	C29—C30	1.377 (3)
C13—H13	0.9300	C29—H29	0.9300
C14—H14	0.9300	C30—H30	0.9300
C15—C16	1.501 (3)	C31—C32	1.497 (3)
C16—H16A	0.9600	C32—H32A	0.9600
C16—H16B	0.9600	C32—H32B	0.9600
C16—H16C	0.9600	C32—H32C	0.9600
O2—S1—O1	119.55 (11)	O4—S2—O5	119.22 (9)
O2—S1—N1	108.66 (10)	O4—S2—N3	105.44 (10)
O1—S1—N1	104.34 (11)	O5—S2—N3	107.14 (9)
O2—S1—C9	108.30 (10)	O4—S2—C25	108.13 (9)
O1—S1—C9	107.73 (10)	O5—S2—C25	108.38 (9)
N1—S1—C9	107.70 (10)	N3—S2—C25	108.06 (9)
C1—N1—S1	119.80 (14)	C17—N3—S2	116.87 (13)
C1—N1—H1N	111.8 (17)	C17—N3—H3N	115.2 (15)
S1—N1—H1N	112.1 (17)	S2—N3—H3N	107.0 (16)
C15—N2—C12	129.42 (18)	C31—N4—C28	128.34 (17)
C15—N2—H2N	114.2 (18)	C31—N4—H4N	114.1 (16)
C12—N2—H2N	116.2 (18)	C28—N4—H4N	117.4 (16)
C6—C1—C2	120.1 (2)	C22—C17—C18	120.5 (2)
C6—C1—N1	120.9 (2)	C22—C17—N3	121.19 (19)
C2—C1—N1	118.9 (2)	C18—C17—N3	118.32 (18)
C3—C2—C1	119.4 (3)	C17—C18—C19	121.0 (2)
C3—C2—H2	120.3	C17—C18—H18	119.5
C1—C2—H2	120.3	C19—C18—H18	119.5
C4—C3—C2	121.7 (2)	C18—C19—C20	118.8 (2)
C4—C3—H3	119.2	C18—C19—C23	119.1 (2)
C2—C3—H3	119.2	C20—C19—C23	122.1 (2)
C3—C4—C5	119.7 (2)	C21—C20—C19	118.8 (2)
C3—C4—C7	120.9 (3)	C21—C20—C24	120.0 (3)
C5—C4—C7	119.3 (3)	C19—C20—C24	121.2 (3)
C4—C5—C6	118.7 (2)	C22—C21—C20	122.1 (2)
C4—C5—C8	122.4 (3)	C22—C21—H21	119.0
C6—C5—C8	118.8 (2)	C20—C21—H21	119.0
C1—C6—C5	120.4 (2)	C17—C22—C21	118.8 (2)
C1—C6—H6	119.8	C17—C22—H22	120.6
C5—C6—H6	119.8	C21—C22—H22	120.6
C4—C7—H7A	109.5	C19—C23—H23A	109.5
C4—C7—H7B	109.5	C19—C23—H23B	109.5
H7A—C7—H7B	109.5	H23A—C23—H23B	109.5
C4—C7—H7C	109.5	C19—C23—H23C	109.5
H7A—C7—H7C	109.5	H23A—C23—H23C	109.5
H7B—C7—H7C	109.5	H23B—C23—H23C	109.5
C5—C8—H8A	109.5	C20—C24—H24A	109.5
C5—C8—H8B	109.5	C20—C24—H24B	109.5
H8A—C8—H8B	109.5	H24A—C24—H24B	109.5
C5—C8—H8C	109.5	C20—C24—H24C	109.5
H8A—C8—H8C	109.5	H24A—C24—H24C	109.5
H8B—C8—H8C	109.5	H24B—C24—H24C	109.5
C14—C9—C10	120.07 (18)	C30—C25—C26	120.04 (18)
C14—C9—S1	121.03 (16)	C30—C25—S2	119.56 (14)
C10—C9—S1	118.90 (15)	C26—C25—S2	120.33 (15)
C11—C10—C9	119.73 (19)	C27—C26—C25	119.47 (18)
C11—C10—H10	120.1	C27—C26—H26	120.3
C9—C10—H10	120.1	C25—C26—H26	120.3
C10—C11—C12	120.71 (19)	C26—C27—C28	120.75 (17)
C10—C11—H11	119.6	C26—C27—H27	119.6
C12—C11—H11	119.6	C28—C27—H27	119.6
C13—C12—C11	119.18 (19)	C29—C28—C27	119.49 (18)
C13—C12—N2	124.18 (18)	C29—C28—N4	123.14 (18)
C11—C12—N2	116.63 (18)	C27—C28—N4	117.37 (16)
C14—C13—C12	119.9 (2)	C30—C29—C28	119.55 (19)
C14—C13—H13	120.1	C30—C29—H29	120.2
C12—C13—H13	120.1	C28—C29—H29	120.2
C9—C14—C13	120.4 (2)	C29—C30—C25	120.70 (18)
C9—C14—H14	119.8	C29—C30—H30	119.6
C13—C14—H14	119.8	C25—C30—H30	119.6
O3—C15—N2	123.0 (2)	O6—C31—N4	123.2 (2)
O3—C15—C16	122.0 (2)	O6—C31—C32	122.2 (2)
N2—C15—C16	114.91 (19)	N4—C31—C32	114.7 (2)
C15—C16—H16A	109.5	C31—C32—H32A	109.5
C15—C16—H16B	109.5	C31—C32—H32B	109.5
H16A—C16—H16B	109.5	H32A—C32—H32B	109.5
C15—C16—H16C	109.5	C31—C32—H32C	109.5
H16A—C16—H16C	109.5	H32A—C32—H32C	109.5
H16B—C16—H16C	109.5	H32B—C32—H32C	109.5
O2—S1—N1—C1	−50.44 (18)	O4—S2—N3—C17	−177.69 (14)
O1—S1—N1—C1	−179.04 (16)	O5—S2—N3—C17	−49.72 (16)
C9—S1—N1—C1	66.66 (18)	C25—S2—N3—C17	66.87 (16)
S1—N1—C1—C6	−107.5 (2)	S2—N3—C17—C22	−93.8 (2)
S1—N1—C1—C2	75.9 (2)	S2—N3—C17—C18	85.6 (2)
C6—C1—C2—C3	0.1 (4)	C22—C17—C18—C19	2.7 (3)
N1—C1—C2—C3	176.6 (2)	N3—C17—C18—C19	−176.69 (19)
C1—C2—C3—C4	−0.4 (4)	C17—C18—C19—C20	−0.9 (3)
C2—C3—C4—C5	0.6 (4)	C17—C18—C19—C23	180.0 (2)
C2—C3—C4—C7	−178.7 (3)	C18—C19—C20—C21	−1.7 (3)
C3—C4—C5—C6	−0.5 (4)	C23—C19—C20—C21	177.3 (2)
C7—C4—C5—C6	178.8 (3)	C18—C19—C20—C24	179.4 (2)
C3—C4—C5—C8	−179.4 (3)	C23—C19—C20—C24	−1.6 (4)
C7—C4—C5—C8	−0.2 (4)	C19—C20—C21—C22	2.8 (4)
C2—C1—C6—C5	0.0 (3)	C24—C20—C21—C22	−178.3 (2)
N1—C1—C6—C5	−176.5 (2)	C18—C17—C22—C21	−1.7 (3)
C4—C5—C6—C1	0.2 (3)	N3—C17—C22—C21	177.7 (2)
C8—C5—C6—C1	179.2 (2)	C20—C21—C22—C17	−1.1 (4)
O2—S1—C9—C14	4.5 (2)	O4—S2—C25—C30	157.72 (17)
O1—S1—C9—C14	135.1 (2)	O5—S2—C25—C30	27.17 (19)
N1—S1—C9—C14	−112.9 (2)	N3—S2—C25—C30	−88.61 (18)
O2—S1—C9—C10	−174.89 (18)	O4—S2—C25—C26	−25.36 (19)
O1—S1—C9—C10	−44.3 (2)	O5—S2—C25—C26	−155.90 (16)
N1—S1—C9—C10	67.8 (2)	N3—S2—C25—C26	88.32 (17)
C14—C9—C10—C11	0.6 (4)	C30—C25—C26—C27	−0.3 (3)
S1—C9—C10—C11	−179.98 (19)	S2—C25—C26—C27	−177.26 (15)
C9—C10—C11—C12	0.4 (4)	C25—C26—C27—C28	0.3 (3)
C10—C11—C12—C13	−1.4 (4)	C26—C27—C28—C29	−0.1 (3)
C10—C11—C12—N2	179.4 (2)	C26—C27—C28—N4	179.47 (18)
C15—N2—C12—C13	−0.1 (4)	C31—N4—C28—C29	0.6 (3)
C15—N2—C12—C11	179.1 (2)	C31—N4—C28—C27	−178.9 (2)
C11—C12—C13—C14	1.4 (4)	C27—C28—C29—C30	0.0 (3)
N2—C12—C13—C14	−179.4 (2)	N4—C28—C29—C30	−179.6 (2)
C10—C9—C14—C13	−0.6 (4)	C28—C29—C30—C25	0.0 (3)
S1—C9—C14—C13	−180.0 (2)	C26—C25—C30—C29	0.2 (3)
C12—C13—C14—C9	−0.4 (4)	S2—C25—C30—C29	177.16 (17)
C12—N2—C15—O3	0.5 (4)	C28—N4—C31—O6	−3.2 (4)
C12—N2—C15—C16	−179.0 (2)	C28—N4—C31—C32	175.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O3i	0.86 (2)	2.07 (2)	2.909 (3)	164 (2)
N2—H2n···O4ii	0.88 (2)	2.08 (2)	2.931 (3)	162.6 (19)
N3—H3n···O1iii	0.870 (19)	2.107 (19)	2.960 (3)	166 (2)
N4—H4n···O5iii	0.869 (19)	2.18 (2)	3.036 (2)	169.5 (19)
C8—H8b···O6iv	0.96	2.71	3.640 (3)	163
C6—H6···O6iv	0.93	2.67	3.541 (3)	156
C16—H16c···O6v	0.96	2.65	3.477 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O3i	0.86 (2)	2.07 (2)	2.909 (3)	164 (2)
N2—H2n⋯O4ii	0.88 (2)	2.08 (2)	2.931 (3)	163 (2)
N3—H3n⋯O1iii	0.87 (2)	2.11 (2)	2.960 (3)	166 (2)
N4—H4n⋯O5iii	0.87 (2)	2.18 (2)	3.036 (2)	170 (2)
C8—H8b⋯O6iv	0.96	2.71	3.640 (3)	163
C6—H6⋯O6iv	0.93	2.67	3.541 (3)	156
C16—H16c⋯O6v	0.96	2.65	3.477 (3)	145

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