N-(2,3-Dimethyl-phen-yl)-2,4-dimethyl-benzene-sulfonamide.

The asymmetric unit of the title compound, C(16)H(19)NO(2)S, contains two independent mol-ecules: the dihedral angles between the sulfonyl and anilino benzene rings in the two mol-ecules are 41.5 (1) and 43.8 (1)°. The independent mol-ecules are linked into a dimer by a pair of inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For our studies of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2009 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C16H19NO2S

M = 289.38

Triclinic,

a = 8.3643 (7) Å

b = 10.975 (1) Å

c = 16.996 (2) Å

α = 83.034 (9)°

β = 80.100 (7)°

γ = 81.796 (9)°

V = 1513.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 299 K

0.34 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.931, T max = 0.958

11164 measured reflections

6136 independent reflections

4196 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.161

S = 1.03

6136 reflections

375 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011669/ci5070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011669/ci5070Isup2.hkl

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

C16H19NO2S	Z = 4
Mr = 289.38	F(000) = 616
Triclinic, P1	Dx = 1.270 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3643 (7) Å	Cell parameters from 3007 reflections
b = 10.975 (1) Å	θ = 2.5–28.0°
c = 16.996 (2) Å	µ = 0.22 mm−1
α = 83.034 (9)°	T = 299 K
β = 80.100 (7)°	Prism, yellow
γ = 81.796 (9)°	0.34 × 0.30 × 0.20 mm
V = 1513.7 (3) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	6136 independent reflections
Radiation source: fine-focus sealed tube	4196 reflections with I > 2σ(I)
graphite	Rint = 0.016
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→10
Tmin = 0.931, Tmax = 0.958	k = −13→13
11164 measured reflections	l = −21→21

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0699P)2 + 0.9151P] where P = (Fo2 + 2Fc2)/3
6136 reflections	(Δ/σ)max = 0.002
375 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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 > 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	0.7579 (3)	0.1917 (2)	0.30498 (15)	0.0439 (6)
C2	0.8079 (3)	0.0826 (2)	0.35144 (17)	0.0487 (6)
C3	0.6896 (4)	0.0046 (3)	0.38031 (18)	0.0559 (7)
H3	0.7200	−0.0685	0.4110	0.067*
C4	0.5295 (4)	0.0283 (3)	0.36652 (18)	0.0548 (7)
C5	0.4848 (4)	0.1366 (3)	0.32071 (19)	0.0582 (8)
H5	0.3781	0.1550	0.3101	0.070*
C6	0.5965 (3)	0.2167 (3)	0.29087 (18)	0.0532 (7)
H6	0.5642	0.2895	0.2605	0.064*
C7	0.9403 (3)	0.3704 (2)	0.40309 (15)	0.0405 (6)
C8	1.1020 (3)	0.3881 (2)	0.40397 (16)	0.0431 (6)
C9	1.1659 (4)	0.3549 (3)	0.47568 (18)	0.0532 (7)
C10	1.0649 (5)	0.3099 (3)	0.54282 (18)	0.0649 (9)
H10	1.1067	0.2888	0.5906	0.078*
C11	0.9048 (5)	0.2950 (3)	0.54161 (19)	0.0664 (9)
H11	0.8397	0.2652	0.5880	0.080*
C12	0.8422 (4)	0.3247 (3)	0.47111 (18)	0.0545 (7)
H12	0.7346	0.3142	0.4692	0.065*
C13	0.9783 (4)	0.0452 (3)	0.3710 (2)	0.0703 (9)
H13A	1.0148	0.1136	0.3902	0.084*
H13B	1.0510	0.0220	0.3235	0.084*
H13C	0.9778	−0.0236	0.4116	0.084*
C14	0.4087 (4)	−0.0607 (3)	0.4010 (2)	0.0770 (10)
H14A	0.4628	−0.1313	0.4293	0.092*
H14B	0.3640	−0.0869	0.3584	0.092*
H14C	0.3221	−0.0206	0.4374	0.092*
C15	1.2017 (4)	0.4467 (3)	0.33078 (19)	0.0594 (8)
H15A	1.1299	0.4970	0.2980	0.071*
H15B	1.2662	0.3833	0.3007	0.071*
H15C	1.2725	0.4973	0.3469	0.071*
C16	1.3387 (4)	0.3701 (4)	0.4809 (2)	0.0815 (11)
H16A	1.3584	0.4534	0.4616	0.098*
H16B	1.4123	0.3136	0.4486	0.098*
H16C	1.3563	0.3531	0.5357	0.098*
N1	0.8735 (3)	0.4042 (2)	0.32974 (14)	0.0487 (6)
H1N	0.783 (4)	0.447 (3)	0.3348 (18)	0.058*
O1	0.8196 (3)	0.37379 (19)	0.19753 (12)	0.0638 (6)
O2	1.0524 (2)	0.24770 (19)	0.25134 (12)	0.0596 (5)
S1	0.88758 (9)	0.30509 (6)	0.26408 (4)	0.0484 (2)
C17	0.6666 (3)	0.7822 (2)	0.21219 (16)	0.0459 (6)
C18	0.6232 (3)	0.8894 (2)	0.16309 (18)	0.0503 (7)
C19	0.7455 (4)	0.9638 (3)	0.1334 (2)	0.0621 (8)
H19	0.7199	1.0352	0.1002	0.075*
C20	0.9028 (4)	0.9375 (3)	0.1505 (2)	0.0621 (8)
C21	0.9409 (4)	0.8305 (3)	0.1997 (2)	0.0644 (9)
H21	1.0461	0.8107	0.2122	0.077*
C22	0.8243 (4)	0.7539 (3)	0.22987 (18)	0.0552 (7)
H22	0.8512	0.6821	0.2625	0.066*
C23	0.4896 (3)	0.6176 (2)	0.10779 (15)	0.0403 (6)
C24	0.6025 (3)	0.6394 (2)	0.03794 (16)	0.0427 (6)
C25	0.5393 (4)	0.6793 (2)	−0.03382 (17)	0.0523 (7)
C26	0.3736 (4)	0.6952 (3)	−0.0335 (2)	0.0615 (8)
H26	0.3337	0.7213	−0.0813	0.074*
C27	0.2650 (4)	0.6736 (3)	0.0354 (2)	0.0628 (8)
H27	0.1531	0.6862	0.0342	0.075*
C28	0.3231 (3)	0.6332 (3)	0.10660 (18)	0.0526 (7)
H28	0.2506	0.6166	0.1534	0.063*
C29	0.4565 (4)	0.9307 (3)	0.1406 (2)	0.0710 (10)
H29A	0.3803	0.9503	0.1878	0.085*
H29B	0.4219	0.8656	0.1172	0.085*
H29C	0.4609	1.0028	0.1026	0.085*
C30	1.0290 (5)	1.0232 (4)	0.1153 (3)	0.0918 (12)
H30A	1.0768	1.0470	0.1577	0.110*
H30B	0.9775	1.0955	0.0875	0.110*
H30C	1.1128	0.9813	0.0784	0.110*
C31	0.7824 (3)	0.6221 (3)	0.03934 (18)	0.0588 (8)
H31A	0.8049	0.5729	0.0878	0.071*
H31B	0.8197	0.7014	0.0373	0.071*
H31C	0.8382	0.5810	−0.0062	0.071*
C32	0.6546 (5)	0.7030 (3)	−0.11119 (19)	0.0778 (10)
H32A	0.7213	0.6273	−0.1243	0.093*
H32B	0.7232	0.7631	−0.1049	0.093*
H32C	0.5925	0.7337	−0.1536	0.093*
N2	0.5434 (3)	0.5754 (2)	0.18338 (14)	0.0469 (5)
H2N	0.627 (4)	0.532 (3)	0.1814 (18)	0.056*
O3	0.5930 (3)	0.59831 (19)	0.31781 (12)	0.0651 (6)
O4	0.3674 (2)	0.73252 (18)	0.26308 (12)	0.0575 (5)
S2	0.53042 (9)	0.67152 (6)	0.25099 (4)	0.0487 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0468 (15)	0.0455 (14)	0.0409 (15)	0.0010 (11)	−0.0121 (11)	−0.0104 (12)
C2	0.0506 (16)	0.0447 (14)	0.0516 (16)	0.0046 (12)	−0.0169 (13)	−0.0076 (12)
C3	0.0653 (19)	0.0428 (15)	0.0594 (19)	−0.0036 (13)	−0.0149 (15)	−0.0011 (13)
C4	0.0581 (18)	0.0546 (16)	0.0546 (18)	−0.0077 (14)	−0.0093 (14)	−0.0154 (14)
C5	0.0461 (16)	0.0651 (18)	0.066 (2)	−0.0035 (14)	−0.0159 (14)	−0.0128 (16)
C6	0.0520 (16)	0.0534 (16)	0.0555 (18)	0.0040 (13)	−0.0212 (13)	−0.0045 (13)
C7	0.0483 (15)	0.0314 (12)	0.0427 (14)	−0.0057 (10)	−0.0086 (11)	−0.0037 (10)
C8	0.0499 (15)	0.0370 (13)	0.0423 (15)	−0.0060 (11)	−0.0057 (11)	−0.0051 (11)
C9	0.0568 (17)	0.0502 (15)	0.0555 (18)	0.0025 (13)	−0.0174 (14)	−0.0156 (14)
C10	0.100 (3)	0.0516 (17)	0.0416 (17)	0.0086 (17)	−0.0207 (17)	−0.0049 (14)
C11	0.096 (3)	0.0519 (17)	0.0432 (18)	−0.0120 (17)	0.0093 (16)	0.0029 (14)
C12	0.0590 (18)	0.0488 (15)	0.0526 (18)	−0.0138 (13)	0.0055 (13)	−0.0047 (13)
C13	0.061 (2)	0.0565 (18)	0.094 (3)	0.0012 (15)	−0.0319 (18)	0.0124 (17)
C14	0.073 (2)	0.077 (2)	0.086 (3)	−0.0253 (18)	−0.0081 (19)	−0.010 (2)
C15	0.0515 (17)	0.0656 (18)	0.0616 (19)	−0.0195 (14)	−0.0001 (14)	−0.0060 (15)
C16	0.065 (2)	0.099 (3)	0.089 (3)	0.0086 (19)	−0.0332 (19)	−0.036 (2)
N1	0.0485 (13)	0.0439 (12)	0.0538 (14)	0.0008 (10)	−0.0144 (11)	−0.0041 (11)
O1	0.0778 (14)	0.0661 (13)	0.0476 (12)	−0.0039 (11)	−0.0223 (10)	0.0064 (10)
O2	0.0529 (12)	0.0671 (13)	0.0570 (13)	−0.0047 (10)	−0.0030 (9)	−0.0103 (10)
S1	0.0531 (4)	0.0499 (4)	0.0421 (4)	−0.0027 (3)	−0.0118 (3)	−0.0021 (3)
C17	0.0507 (16)	0.0436 (14)	0.0448 (15)	−0.0017 (12)	−0.0113 (12)	−0.0093 (12)
C18	0.0495 (16)	0.0418 (14)	0.0612 (18)	−0.0015 (12)	−0.0141 (13)	−0.0090 (13)
C19	0.064 (2)	0.0461 (16)	0.078 (2)	−0.0048 (14)	−0.0169 (16)	−0.0052 (15)
C20	0.0514 (18)	0.0637 (19)	0.075 (2)	−0.0111 (14)	−0.0056 (15)	−0.0245 (17)
C21	0.0495 (17)	0.074 (2)	0.075 (2)	0.0061 (15)	−0.0213 (16)	−0.0271 (18)
C22	0.0545 (17)	0.0564 (17)	0.0567 (18)	0.0027 (14)	−0.0185 (14)	−0.0110 (14)
C23	0.0491 (15)	0.0332 (12)	0.0379 (14)	−0.0036 (10)	−0.0058 (11)	−0.0042 (10)
C24	0.0499 (15)	0.0365 (12)	0.0429 (15)	−0.0088 (11)	−0.0066 (11)	−0.0058 (11)
C25	0.073 (2)	0.0433 (14)	0.0434 (16)	−0.0117 (13)	−0.0124 (14)	−0.0041 (12)
C26	0.080 (2)	0.0523 (17)	0.058 (2)	−0.0022 (15)	−0.0328 (17)	−0.0041 (14)
C27	0.0535 (18)	0.0624 (19)	0.079 (2)	−0.0035 (14)	−0.0242 (17)	−0.0161 (17)
C28	0.0459 (16)	0.0538 (16)	0.0580 (18)	−0.0101 (12)	−0.0029 (13)	−0.0086 (14)
C29	0.0588 (19)	0.0538 (18)	0.100 (3)	−0.0028 (15)	−0.0298 (18)	0.0126 (18)
C30	0.067 (2)	0.090 (3)	0.124 (4)	−0.025 (2)	−0.008 (2)	−0.024 (2)
C31	0.0499 (17)	0.0703 (19)	0.0556 (18)	−0.0144 (14)	0.0005 (13)	−0.0076 (15)
C32	0.109 (3)	0.077 (2)	0.0454 (19)	−0.022 (2)	−0.0035 (18)	0.0044 (17)
N2	0.0525 (14)	0.0437 (12)	0.0413 (13)	−0.0003 (10)	−0.0061 (11)	−0.0001 (10)
O3	0.0854 (15)	0.0675 (13)	0.0381 (11)	0.0013 (11)	−0.0128 (10)	0.0030 (10)
O4	0.0536 (12)	0.0617 (12)	0.0523 (12)	−0.0006 (9)	0.0027 (9)	−0.0089 (10)
S2	0.0574 (4)	0.0501 (4)	0.0362 (4)	−0.0020 (3)	−0.0062 (3)	−0.0025 (3)

C1—C6	1.395 (4)	C17—C22	1.386 (4)
C1—C2	1.405 (4)	C17—C18	1.399 (4)
C1—S1	1.768 (3)	C17—S2	1.775 (3)
C2—C3	1.387 (4)	C18—C19	1.389 (4)
C2—C13	1.508 (4)	C18—C29	1.501 (4)
C3—C4	1.382 (4)	C19—C20	1.379 (4)
C3—H3	0.93	C19—H19	0.93
C4—C5	1.381 (4)	C20—C21	1.388 (4)
C4—C14	1.502 (4)	C20—C30	1.512 (5)
C5—C6	1.366 (4)	C21—C22	1.371 (4)
C5—H5	0.93	C21—H21	0.93
C6—H6	0.93	C22—H22	0.93
C7—C12	1.383 (4)	C23—C28	1.382 (4)
C7—C8	1.397 (3)	C23—C24	1.403 (4)
C7—N1	1.440 (3)	C23—N2	1.437 (3)
C8—C9	1.402 (4)	C24—C25	1.409 (4)
C8—C15	1.503 (4)	C24—C31	1.493 (4)
C9—C10	1.382 (4)	C25—C26	1.372 (4)
C9—C16	1.497 (4)	C25—C32	1.509 (4)
C10—C11	1.376 (5)	C26—C27	1.371 (5)
C10—H10	0.93	C26—H26	0.93
C11—C12	1.374 (4)	C27—C28	1.381 (4)
C11—H11	0.93	C27—H27	0.93
C12—H12	0.93	C28—H28	0.93
C13—H13A	0.96	C29—H29A	0.96
C13—H13B	0.96	C29—H29B	0.96
C13—H13C	0.96	C29—H29C	0.96
C14—H14A	0.96	C30—H30A	0.96
C14—H14B	0.96	C30—H30B	0.96
C14—H14C	0.96	C30—H30C	0.96
C15—H15A	0.96	C31—H31A	0.96
C15—H15B	0.96	C31—H31B	0.96
C15—H15C	0.96	C31—H31C	0.96
C16—H16A	0.96	C32—H32A	0.96
C16—H16B	0.96	C32—H32B	0.96
C16—H16C	0.96	C32—H32C	0.96
N1—S1	1.630 (2)	N2—S2	1.632 (2)
N1—H1N	0.83 (3)	N2—H2N	0.79 (3)
O1—S1	1.436 (2)	O3—S2	1.439 (2)
O2—S1	1.424 (2)	O4—S2	1.423 (2)
C6—C1—C2	119.8 (3)	C22—C17—C18	120.8 (3)
C6—C1—S1	116.4 (2)	C22—C17—S2	116.1 (2)
C2—C1—S1	123.8 (2)	C18—C17—S2	123.0 (2)
C3—C2—C1	116.4 (2)	C19—C18—C17	116.6 (3)
C3—C2—C13	118.8 (3)	C19—C18—C29	117.8 (3)
C1—C2—C13	124.8 (3)	C17—C18—C29	125.7 (3)
C4—C3—C2	124.3 (3)	C20—C19—C18	123.6 (3)
C4—C3—H3	117.9	C20—C19—H19	118.2
C2—C3—H3	117.9	C18—C19—H19	118.2
C5—C4—C3	117.7 (3)	C19—C20—C21	118.1 (3)
C5—C4—C14	121.5 (3)	C19—C20—C30	120.2 (3)
C3—C4—C14	120.8 (3)	C21—C20—C30	121.7 (3)
C6—C5—C4	120.3 (3)	C22—C21—C20	120.3 (3)
C6—C5—H5	119.8	C22—C21—H21	119.8
C4—C5—H5	119.8	C20—C21—H21	119.8
C5—C6—C1	121.5 (3)	C21—C22—C17	120.7 (3)
C5—C6—H6	119.3	C21—C22—H22	119.7
C1—C6—H6	119.3	C17—C22—H22	119.7
C12—C7—C8	121.8 (3)	C28—C23—C24	121.7 (2)
C12—C7—N1	119.5 (2)	C28—C23—N2	117.3 (2)
C8—C7—N1	118.7 (2)	C24—C23—N2	120.9 (2)
C7—C8—C9	118.3 (2)	C23—C24—C25	117.3 (2)
C7—C8—C15	120.5 (2)	C23—C24—C31	121.6 (2)
C9—C8—C15	121.1 (3)	C25—C24—C31	121.1 (3)
C10—C9—C8	118.7 (3)	C26—C25—C24	120.0 (3)
C10—C9—C16	120.1 (3)	C26—C25—C32	120.1 (3)
C8—C9—C16	121.2 (3)	C24—C25—C32	119.8 (3)
C11—C10—C9	122.5 (3)	C25—C26—C27	121.9 (3)
C11—C10—H10	118.8	C25—C26—H26	119.1
C9—C10—H10	118.8	C27—C26—H26	119.1
C12—C11—C10	119.2 (3)	C26—C27—C28	119.5 (3)
C12—C11—H11	120.4	C26—C27—H27	120.2
C10—C11—H11	120.4	C28—C27—H27	120.2
C11—C12—C7	119.5 (3)	C27—C28—C23	119.6 (3)
C11—C12—H12	120.2	C27—C28—H28	120.2
C7—C12—H12	120.2	C23—C28—H28	120.2
C2—C13—H13A	109.5	C18—C29—H29A	109.5
C2—C13—H13B	109.5	C18—C29—H29B	109.5
H13A—C13—H13B	109.5	H29A—C29—H29B	109.5
C2—C13—H13C	109.5	C18—C29—H29C	109.5
H13A—C13—H13C	109.5	H29A—C29—H29C	109.5
H13B—C13—H13C	109.5	H29B—C29—H29C	109.5
C4—C14—H14A	109.5	C20—C30—H30A	109.5
C4—C14—H14B	109.5	C20—C30—H30B	109.5
H14A—C14—H14B	109.5	H30A—C30—H30B	109.5
C4—C14—H14C	109.5	C20—C30—H30C	109.5
H14A—C14—H14C	109.5	H30A—C30—H30C	109.5
H14B—C14—H14C	109.5	H30B—C30—H30C	109.5
C8—C15—H15A	109.5	C24—C31—H31A	109.5
C8—C15—H15B	109.5	C24—C31—H31B	109.5
H15A—C15—H15B	109.5	H31A—C31—H31B	109.5
C8—C15—H15C	109.5	C24—C31—H31C	109.5
H15A—C15—H15C	109.5	H31A—C31—H31C	109.5
H15B—C15—H15C	109.5	H31B—C31—H31C	109.5
C9—C16—H16A	109.5	C25—C32—H32A	109.5
C9—C16—H16B	109.5	C25—C32—H32B	109.5
H16A—C16—H16B	109.5	H32A—C32—H32B	109.5
C9—C16—H16C	109.5	C25—C32—H32C	109.5
H16A—C16—H16C	109.5	H32A—C32—H32C	109.5
H16B—C16—H16C	109.5	H32B—C32—H32C	109.5
C7—N1—S1	121.05 (17)	C23—N2—S2	120.16 (17)
C7—N1—H1N	115 (2)	C23—N2—H2N	116 (2)
S1—N1—H1N	112 (2)	S2—N2—H2N	110 (2)
O2—S1—O1	119.10 (13)	O4—S2—O3	118.80 (13)
O2—S1—N1	107.81 (12)	O4—S2—N2	108.11 (12)
O1—S1—N1	105.08 (12)	O3—S2—N2	104.97 (12)
O2—S1—C1	109.11 (12)	O4—S2—C17	109.21 (12)
O1—S1—C1	107.12 (13)	O3—S2—C17	107.64 (13)
N1—S1—C1	108.16 (12)	N2—S2—C17	107.58 (12)
C6—C1—C2—C3	0.5 (4)	C22—C17—C18—C19	0.3 (4)
S1—C1—C2—C3	178.7 (2)	S2—C17—C18—C19	−176.3 (2)
C6—C1—C2—C13	−179.9 (3)	C22—C17—C18—C29	−179.1 (3)
S1—C1—C2—C13	−1.8 (4)	S2—C17—C18—C29	4.2 (4)
C1—C2—C3—C4	−0.4 (4)	C17—C18—C19—C20	−0.6 (5)
C13—C2—C3—C4	−180.0 (3)	C29—C18—C19—C20	178.9 (3)
C2—C3—C4—C5	0.3 (4)	C18—C19—C20—C21	0.3 (5)
C2—C3—C4—C14	−179.2 (3)	C18—C19—C20—C30	179.7 (3)
C3—C4—C5—C6	−0.3 (4)	C19—C20—C21—C22	0.1 (5)
C14—C4—C5—C6	179.2 (3)	C30—C20—C21—C22	−179.2 (3)
C4—C5—C6—C1	0.5 (4)	C20—C21—C22—C17	−0.4 (5)
C2—C1—C6—C5	−0.6 (4)	C18—C17—C22—C21	0.1 (4)
S1—C1—C6—C5	−178.9 (2)	S2—C17—C22—C21	177.0 (2)
C12—C7—C8—C9	1.9 (4)	C28—C23—C24—C25	0.6 (4)
N1—C7—C8—C9	180.0 (2)	N2—C23—C24—C25	179.3 (2)
C12—C7—C8—C15	−175.4 (2)	C28—C23—C24—C31	−179.8 (2)
N1—C7—C8—C15	2.7 (4)	N2—C23—C24—C31	−1.2 (4)
C7—C8—C9—C10	−2.0 (4)	C23—C24—C25—C26	−0.1 (4)
C15—C8—C9—C10	175.2 (3)	C31—C24—C25—C26	−179.6 (3)
C7—C8—C9—C16	179.4 (3)	C23—C24—C25—C32	−179.3 (3)
C15—C8—C9—C16	−3.4 (4)	C31—C24—C25—C32	1.1 (4)
C8—C9—C10—C11	0.9 (4)	C24—C25—C26—C27	0.2 (4)
C16—C9—C10—C11	179.4 (3)	C32—C25—C26—C27	179.5 (3)
C9—C10—C11—C12	0.6 (5)	C25—C26—C27—C28	−0.9 (5)
C10—C11—C12—C7	−0.8 (4)	C26—C27—C28—C23	1.4 (4)
C8—C7—C12—C11	−0.4 (4)	C24—C23—C28—C27	−1.3 (4)
N1—C7—C12—C11	−178.5 (2)	N2—C23—C28—C27	180.0 (2)
C12—C7—N1—S1	−91.8 (3)	C28—C23—N2—S2	−77.9 (3)
C8—C7—N1—S1	90.0 (3)	C24—C23—N2—S2	103.4 (2)
C7—N1—S1—O2	−47.8 (2)	C23—N2—S2—O4	51.8 (2)
C7—N1—S1—O1	−175.8 (2)	C23—N2—S2—O3	179.5 (2)
C7—N1—S1—C1	70.1 (2)	C23—N2—S2—C17	−66.0 (2)
C6—C1—S1—O2	−154.2 (2)	C22—C17—S2—O4	152.1 (2)
C2—C1—S1—O2	27.5 (3)	C18—C17—S2—O4	−31.1 (3)
C6—C1—S1—O1	−24.0 (2)	C22—C17—S2—O3	21.9 (2)
C2—C1—S1—O1	157.7 (2)	C18—C17—S2—O3	−161.3 (2)
C6—C1—S1—N1	88.8 (2)	C22—C17—S2—N2	−90.8 (2)
C2—C1—S1—N1	−89.5 (2)	C18—C17—S2—N2	86.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.83 (3)	2.15 (3)	2.952 (3)	161 (3)
N2—H2N···O1	0.79 (3)	2.22 (3)	2.982 (3)	164 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.83 (3)	2.15 (3)	2.952 (3)	161 (3)
N2—H2N⋯O1	0.79 (3)	2.22 (3)	2.982 (3)	164 (3)