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

The asymmetric unit of the crystal of the title compound, C(15)H(17)NO(2)S, contains two independent mol-ecules, which are twisted at the S-N bonds with C-SO(2)-NH-C torsion angles of 48.3 (2) (mol-ecule 1) and -75.7 (3)° (mol-ecule 2). The dihedral angles between the benzene rings are 72.0 (1) (mol-ecule 1) and 78.3 (1)° (mol-ecule 2). The crystal structure features inversion dimers linked by pairs of 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 ▶); Nirmala et al. (2009 ▶, 2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C15H17NO2S

M = 275.36

Monoclinic,

a = 10.623 (1) Å

b = 10.770 (1) Å

c = 25.513 (2) Å

β = 97.927 (6)°

V = 2891.0 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 299 K

0.40 × 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 = 0.917, T max = 0.957

10876 measured reflections

5282 independent reflections

3743 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.116

S = 1.03

5282 reflections

355 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.23 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/S1600536810049627/bq2257sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049627/bq2257Isup2.hkl

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

C15H17NO2S	F(000) = 1168
Mr = 275.36	Dx = 1.265 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2957 reflections
a = 10.623 (1) Å	θ = 2.7–27.9°
b = 10.770 (1) Å	µ = 0.22 mm−1
c = 25.513 (2) Å	T = 299 K
β = 97.927 (6)°	Prism, colourless
V = 2891.0 (4) Å3	0.40 × 0.30 × 0.20 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5282 independent reflections
Radiation source: fine-focus sealed tube	3743 reflections with I > 2σ(I)
graphite	Rint = 0.017
Rotation method data acquisition using ω and phi scans	θmax = 25.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −12→10
Tmin = 0.917, Tmax = 0.957	k = −12→11
10876 measured reflections	l = −26→30

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0588P)2 + 0.5667P] where P = (Fo2 + 2Fc2)/3
5282 reflections	(Δ/σ)max = 0.009
355 parameters	Δρmax = 0.20 e Å−3
3 restraints	Δρmin = −0.23 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S1	0.16582 (5)	0.91378 (5)	0.253220 (19)	0.04951 (16)
O1	0.16198 (14)	1.03883 (14)	0.23457 (6)	0.0619 (4)
O2	0.09258 (13)	0.88329 (15)	0.29500 (5)	0.0625 (4)
N1	0.31153 (16)	0.87937 (18)	0.27751 (6)	0.0543 (5)
H1N	0.311 (2)	0.8300 (18)	0.3034 (7)	0.065*
C1	0.12183 (16)	0.81649 (19)	0.19825 (7)	0.0437 (5)
C2	0.12013 (18)	0.6871 (2)	0.20238 (8)	0.0520 (5)
C3	0.0833 (2)	0.6212 (2)	0.15577 (9)	0.0616 (6)
H3	0.0810	0.5350	0.1576	0.074*
C4	0.0500 (2)	0.6771 (2)	0.10694 (9)	0.0615 (6)
C5	0.0507 (2)	0.8053 (3)	0.10508 (8)	0.0639 (6)
H5	0.0264	0.8452	0.0729	0.077*
C6	0.08644 (19)	0.8752 (2)	0.14974 (8)	0.0538 (5)
H6	0.0870	0.9614	0.1476	0.065*
C7	0.41385 (18)	0.8671 (2)	0.24720 (7)	0.0472 (5)
C8	0.5031 (2)	0.7771 (2)	0.26186 (9)	0.0666 (6)
H8	0.4941	0.7249	0.2901	0.080*
C9	0.6063 (2)	0.7634 (3)	0.23492 (11)	0.0761 (7)
H9	0.6663	0.7025	0.2458	0.091*
C10	0.6230 (2)	0.8373 (2)	0.19238 (9)	0.0612 (6)
C11	0.5324 (2)	0.9270 (2)	0.17813 (9)	0.0611 (6)
H11	0.5413	0.9788	0.1497	0.073*
C12	0.4286 (2)	0.9428 (2)	0.20474 (9)	0.0582 (6)
H12	0.3689	1.0041	0.1941	0.070*
C13	0.1564 (3)	0.6158 (2)	0.25302 (10)	0.0769 (7)
H13A	0.1038	0.6417	0.2787	0.092*
H13B	0.2439	0.6316	0.2663	0.092*
H13C	0.1446	0.5286	0.2463	0.092*
C14	0.0177 (3)	0.5997 (3)	0.05741 (10)	0.0884 (9)
H14A	0.0130	0.5138	0.0669	0.106*
H14B	0.0824	0.6104	0.0350	0.106*
H14C	−0.0627	0.6258	0.0389	0.106*
C15	0.7355 (3)	0.8194 (3)	0.16271 (12)	0.0923 (9)
H15A	0.7062	0.7916	0.1274	0.111*
H15B	0.7919	0.7585	0.1806	0.111*
H15C	0.7798	0.8968	0.1613	0.111*
S2	0.75114 (5)	0.19437 (7)	0.08416 (2)	0.0658 (2)
O3	0.67144 (15)	0.23202 (19)	0.12238 (6)	0.0836 (6)
O4	0.75504 (17)	0.06565 (18)	0.07007 (6)	0.0795 (5)
N2	0.89188 (18)	0.2396 (2)	0.10928 (7)	0.0728 (6)
H2N	0.892 (2)	0.284 (2)	0.1371 (7)	0.087*
C16	0.70689 (18)	0.2795 (2)	0.02500 (8)	0.0569 (6)
C17	0.6886 (2)	0.4078 (3)	0.02402 (10)	0.0677 (7)
C18	0.6524 (2)	0.4629 (3)	−0.02539 (12)	0.0800 (8)
H18	0.6401	0.5484	−0.0268	0.096*
C19	0.6339 (2)	0.3966 (3)	−0.07224 (11)	0.0761 (7)
C20	0.6518 (2)	0.2702 (3)	−0.06978 (9)	0.0737 (7)
H20	0.6392	0.2236	−0.1007	0.088*
C21	0.6883 (2)	0.2111 (3)	−0.02178 (8)	0.0647 (6)
H21	0.7003	0.1256	−0.0208	0.078*
C22	1.00993 (19)	0.2099 (2)	0.09259 (8)	0.0547 (5)
C23	1.0219 (2)	0.1542 (3)	0.04490 (8)	0.0709 (7)
H23	0.9497	0.1309	0.0222	0.085*
C24	1.1411 (2)	0.1330 (3)	0.03075 (9)	0.0716 (7)
H24	1.1473	0.0951	−0.0016	0.086*
C25	1.2500 (2)	0.1658 (2)	0.06267 (11)	0.0655 (6)
C26	1.2360 (2)	0.2188 (2)	0.11096 (11)	0.0740 (7)
H26	1.3085	0.2403	0.1339	0.089*
C27	1.1183 (2)	0.2407 (2)	0.12624 (9)	0.0626 (6)
H27	1.1121	0.2761	0.1590	0.075*
C28	0.5989 (3)	0.4606 (4)	−0.12494 (13)	0.1115 (11)
H28A	0.6747	0.4790	−0.1400	0.134*
H28B	0.5545	0.5363	−0.1199	0.134*
H28C	0.5452	0.4071	−0.1484	0.134*
C29	0.7054 (3)	0.4885 (3)	0.07303 (12)	0.0962 (9)
H29A	0.7878	0.4738	0.0927	0.115*
H29B	0.6410	0.4686	0.0946	0.115*
H29C	0.6982	0.5743	0.0629	0.115*
C30	1.3795 (2)	0.1458 (3)	0.04557 (14)	0.0971 (10)
H30A	1.3696	0.1275	0.0084	0.117*
H30B	1.4212	0.0776	0.0650	0.117*
H30C	1.4297	0.2196	0.0525	0.117*

	U11	U22	U33	U12	U13	U23
S1	0.0446 (3)	0.0605 (4)	0.0442 (3)	0.0057 (2)	0.0088 (2)	0.0021 (2)
O1	0.0653 (9)	0.0528 (10)	0.0674 (9)	0.0038 (7)	0.0093 (7)	0.0006 (8)
O2	0.0517 (8)	0.0895 (12)	0.0494 (8)	0.0140 (8)	0.0179 (7)	0.0080 (8)
N1	0.0448 (9)	0.0755 (13)	0.0429 (9)	0.0036 (9)	0.0073 (8)	0.0052 (9)
C1	0.0367 (10)	0.0514 (13)	0.0438 (10)	0.0015 (8)	0.0084 (8)	0.0062 (9)
C2	0.0432 (11)	0.0571 (14)	0.0561 (12)	−0.0066 (9)	0.0086 (9)	0.0082 (11)
C3	0.0567 (13)	0.0556 (14)	0.0742 (15)	−0.0129 (10)	0.0148 (11)	−0.0024 (12)
C4	0.0527 (13)	0.0767 (18)	0.0567 (13)	−0.0161 (12)	0.0129 (10)	−0.0102 (12)
C5	0.0650 (14)	0.0832 (19)	0.0432 (12)	−0.0065 (12)	0.0069 (10)	0.0070 (12)
C6	0.0560 (12)	0.0585 (14)	0.0472 (11)	0.0020 (10)	0.0088 (9)	0.0088 (10)
C7	0.0419 (10)	0.0580 (13)	0.0412 (10)	−0.0027 (9)	0.0037 (8)	−0.0031 (9)
C8	0.0546 (13)	0.0815 (17)	0.0654 (14)	0.0116 (12)	0.0146 (11)	0.0223 (13)
C9	0.0589 (15)	0.0785 (18)	0.0937 (19)	0.0209 (12)	0.0208 (13)	0.0210 (15)
C10	0.0551 (13)	0.0620 (15)	0.0700 (14)	−0.0017 (11)	0.0209 (11)	−0.0031 (12)
C11	0.0640 (14)	0.0621 (15)	0.0606 (13)	−0.0046 (12)	0.0203 (11)	0.0076 (12)
C12	0.0543 (13)	0.0565 (14)	0.0655 (14)	0.0045 (10)	0.0137 (10)	0.0054 (11)
C13	0.0869 (18)	0.0626 (17)	0.0778 (17)	−0.0075 (13)	−0.0017 (14)	0.0199 (13)
C14	0.0858 (19)	0.109 (2)	0.0728 (17)	−0.0318 (16)	0.0184 (14)	−0.0272 (16)
C15	0.0802 (18)	0.095 (2)	0.112 (2)	0.0100 (16)	0.0499 (17)	0.0032 (18)
S2	0.0534 (3)	0.1010 (5)	0.0443 (3)	−0.0202 (3)	0.0115 (2)	−0.0084 (3)
O3	0.0596 (10)	0.1410 (17)	0.0543 (9)	−0.0271 (10)	0.0221 (7)	−0.0182 (10)
O4	0.0850 (11)	0.0914 (9)	0.0616 (10)	−0.0235 (9)	0.0085 (8)	0.0003 (9)
N2	0.0517 (11)	0.1221 (19)	0.0448 (10)	−0.0140 (11)	0.0076 (8)	−0.0212 (11)
C16	0.0397 (11)	0.0814 (18)	0.0505 (12)	−0.0113 (10)	0.0089 (9)	−0.0098 (11)
C17	0.0463 (12)	0.088 (2)	0.0709 (16)	−0.0035 (12)	0.0175 (11)	−0.0183 (14)
C18	0.0618 (15)	0.086 (2)	0.094 (2)	0.0098 (13)	0.0173 (14)	0.0046 (17)
C19	0.0522 (14)	0.106 (2)	0.0698 (16)	0.0003 (14)	0.0069 (12)	0.0066 (17)
C20	0.0617 (15)	0.107 (2)	0.0510 (13)	−0.0126 (14)	0.0024 (11)	−0.0092 (14)
C21	0.0571 (13)	0.0837 (18)	0.0520 (12)	−0.0119 (12)	0.0031 (10)	−0.0120 (12)
C22	0.0502 (12)	0.0702 (15)	0.0426 (11)	−0.0049 (10)	0.0026 (9)	0.0059 (10)
C23	0.0472 (13)	0.121 (2)	0.0422 (11)	−0.0032 (13)	−0.0024 (9)	−0.0094 (13)
C24	0.0551 (14)	0.103 (2)	0.0562 (13)	0.0078 (13)	0.0047 (11)	−0.0046 (13)
C25	0.0454 (12)	0.0638 (16)	0.0845 (17)	0.0013 (11)	−0.0013 (11)	0.0055 (13)
C26	0.0532 (14)	0.0749 (18)	0.0866 (18)	−0.0057 (12)	−0.0158 (12)	−0.0094 (15)
C27	0.0624 (14)	0.0667 (16)	0.0550 (13)	−0.0067 (11)	−0.0054 (11)	−0.0054 (11)
C28	0.086 (2)	0.155 (3)	0.093 (2)	0.019 (2)	0.0118 (17)	0.037 (2)
C29	0.087 (2)	0.102 (2)	0.104 (2)	−0.0038 (16)	0.0286 (16)	−0.0380 (19)
C30	0.0531 (15)	0.098 (2)	0.139 (3)	0.0041 (14)	0.0099 (16)	−0.015 (2)

S1—O1	1.4271 (15)	S2—O4	1.434 (2)
S1—O2	1.4415 (14)	S2—O3	1.4352 (16)
S1—N1	1.6287 (17)	S2—N2	1.6184 (19)
S1—C1	1.761 (2)	S2—C16	1.773 (2)
N1—C7	1.424 (2)	N2—C22	1.416 (3)
N1—H1N	0.849 (9)	N2—H2N	0.852 (10)
C1—C6	1.394 (3)	C16—C21	1.393 (3)
C1—C2	1.398 (3)	C16—C17	1.395 (3)
C2—C3	1.394 (3)	C17—C18	1.398 (4)
C2—C13	1.507 (3)	C17—C29	1.513 (3)
C3—C4	1.384 (3)	C18—C19	1.383 (4)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.382 (3)	C19—C20	1.375 (4)
C4—C14	1.513 (3)	C19—C28	1.511 (4)
C5—C6	1.374 (3)	C20—C21	1.387 (3)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.372 (3)	C22—C27	1.378 (3)
C7—C12	1.382 (3)	C22—C23	1.378 (3)
C8—C9	1.379 (3)	C23—C24	1.382 (3)
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.377 (3)	C24—C25	1.366 (3)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.377 (3)	C25—C26	1.384 (4)
C10—C15	1.513 (3)	C25—C30	1.514 (3)
C11—C12	1.383 (3)	C26—C27	1.381 (3)
C11—H11	0.9300	C26—H26	0.9300
C12—H12	0.9300	C27—H27	0.9300
C13—H13A	0.9600	C28—H28A	0.9600
C13—H13B	0.9600	C28—H28B	0.9600
C13—H13C	0.9600	C28—H28C	0.9600
C14—H14A	0.9600	C29—H29A	0.9600
C14—H14B	0.9600	C29—H29B	0.9600
C14—H14C	0.9600	C29—H29C	0.9600
C15—H15A	0.9600	C30—H30A	0.9600
C15—H15B	0.9600	C30—H30B	0.9600
C15—H15C	0.9600	C30—H30C	0.9600
O1—S1—O2	117.90 (9)	O4—S2—O3	118.92 (11)
O1—S1—N1	108.88 (10)	O4—S2—N2	109.47 (12)
O2—S1—N1	104.38 (9)	O3—S2—N2	104.20 (10)
O1—S1—C1	107.68 (9)	O4—S2—C16	107.45 (11)
O2—S1—C1	110.01 (9)	O3—S2—C16	108.68 (11)
N1—S1—C1	107.55 (9)	N2—S2—C16	107.65 (10)
C7—N1—S1	124.81 (13)	C22—N2—S2	128.39 (16)
C7—N1—H1N	116.7 (16)	C22—N2—H2N	118.2 (18)
S1—N1—H1N	109.5 (15)	S2—N2—H2N	113.3 (18)
C6—C1—C2	120.94 (19)	C21—C16—C17	120.3 (2)
C6—C1—S1	116.52 (16)	C21—C16—S2	116.5 (2)
C2—C1—S1	122.53 (15)	C17—C16—S2	123.18 (18)
C3—C2—C1	116.63 (19)	C16—C17—C18	117.1 (2)
C3—C2—C13	118.7 (2)	C16—C17—C29	123.6 (3)
C1—C2—C13	124.6 (2)	C18—C17—C29	119.2 (3)
C4—C3—C2	123.6 (2)	C19—C18—C17	123.3 (3)
C4—C3—H3	118.2	C19—C18—H18	118.4
C2—C3—H3	118.2	C17—C18—H18	118.4
C5—C4—C3	117.6 (2)	C20—C19—C18	118.0 (3)
C5—C4—C14	121.6 (2)	C20—C19—C28	120.5 (3)
C3—C4—C14	120.8 (2)	C18—C19—C28	121.4 (3)
C6—C5—C4	121.4 (2)	C19—C20—C21	121.0 (2)
C6—C5—H5	119.3	C19—C20—H20	119.5
C4—C5—H5	119.3	C21—C20—H20	119.5
C5—C6—C1	119.8 (2)	C20—C21—C16	120.2 (3)
C5—C6—H6	120.1	C20—C21—H21	119.9
C1—C6—H6	120.1	C16—C21—H21	119.9
C8—C7—C12	118.81 (19)	C27—C22—C23	118.9 (2)
C8—C7—N1	117.91 (18)	C27—C22—N2	117.2 (2)
C12—C7—N1	123.26 (19)	C23—C22—N2	123.90 (19)
C7—C8—C9	120.4 (2)	C22—C23—C24	120.1 (2)
C7—C8—H8	119.8	C22—C23—H23	119.9
C9—C8—H8	119.8	C24—C23—H23	119.9
C10—C9—C8	121.9 (2)	C25—C24—C23	122.2 (2)
C10—C9—H9	119.0	C25—C24—H24	118.9
C8—C9—H9	119.0	C23—C24—H24	118.9
C11—C10—C9	116.9 (2)	C24—C25—C26	116.8 (2)
C11—C10—C15	121.9 (2)	C24—C25—C30	121.3 (2)
C9—C10—C15	121.1 (2)	C26—C25—C30	121.9 (2)
C10—C11—C12	122.2 (2)	C27—C26—C25	122.3 (2)
C10—C11—H11	118.9	C27—C26—H26	118.9
C12—C11—H11	118.9	C25—C26—H26	118.9
C7—C12—C11	119.8 (2)	C22—C27—C26	119.6 (2)
C7—C12—H12	120.1	C22—C27—H27	120.2
C11—C12—H12	120.1	C26—C27—H27	120.2
C2—C13—H13A	109.5	C19—C28—H28A	109.5
C2—C13—H13B	109.5	C19—C28—H28B	109.5
H13A—C13—H13B	109.5	H28A—C28—H28B	109.5
C2—C13—H13C	109.5	C19—C28—H28C	109.5
H13A—C13—H13C	109.5	H28A—C28—H28C	109.5
H13B—C13—H13C	109.5	H28B—C28—H28C	109.5
C4—C14—H14A	109.5	C17—C29—H29A	109.5
C4—C14—H14B	109.5	C17—C29—H29B	109.5
H14A—C14—H14B	109.5	H29A—C29—H29B	109.5
C4—C14—H14C	109.5	C17—C29—H29C	109.5
H14A—C14—H14C	109.5	H29A—C29—H29C	109.5
H14B—C14—H14C	109.5	H29B—C29—H29C	109.5
C10—C15—H15A	109.5	C25—C30—H30A	109.5
C10—C15—H15B	109.5	C25—C30—H30B	109.5
H15A—C15—H15B	109.5	H30A—C30—H30B	109.5
C10—C15—H15C	109.5	C25—C30—H30C	109.5
H15A—C15—H15C	109.5	H30A—C30—H30C	109.5
H15B—C15—H15C	109.5	H30B—C30—H30C	109.5
O1—S1—N1—C7	−68.1 (2)	O4—S2—N2—C22	40.9 (2)
O2—S1—N1—C7	165.14 (18)	O3—S2—N2—C22	169.1 (2)
C1—S1—N1—C7	48.3 (2)	C16—S2—N2—C22	−75.6 (2)
O1—S1—C1—C6	−3.23 (17)	O4—S2—C16—C21	−1.54 (19)
O2—S1—C1—C6	126.48 (15)	O3—S2—C16—C21	−131.43 (17)
N1—S1—C1—C6	−120.42 (15)	N2—S2—C16—C21	116.28 (17)
O1—S1—C1—C2	177.66 (15)	O4—S2—C16—C17	177.29 (17)
O2—S1—C1—C2	−52.64 (18)	O3—S2—C16—C17	47.4 (2)
N1—S1—C1—C2	60.47 (18)	N2—S2—C16—C17	−64.9 (2)
C6—C1—C2—C3	0.9 (3)	C21—C16—C17—C18	−0.5 (3)
S1—C1—C2—C3	179.96 (14)	S2—C16—C17—C18	−179.28 (16)
C6—C1—C2—C13	−179.9 (2)	C21—C16—C17—C29	179.3 (2)
S1—C1—C2—C13	−0.8 (3)	S2—C16—C17—C29	0.5 (3)
C1—C2—C3—C4	0.3 (3)	C16—C17—C18—C19	0.3 (4)
C13—C2—C3—C4	−179.0 (2)	C29—C17—C18—C19	−179.5 (2)
C2—C3—C4—C5	−1.7 (3)	C17—C18—C19—C20	0.2 (4)
C2—C3—C4—C14	176.7 (2)	C17—C18—C19—C28	−178.0 (2)
C3—C4—C5—C6	1.8 (3)	C18—C19—C20—C21	−0.5 (4)
C14—C4—C5—C6	−176.6 (2)	C28—C19—C20—C21	177.7 (2)
C4—C5—C6—C1	−0.6 (3)	C19—C20—C21—C16	0.3 (3)
C2—C1—C6—C5	−0.8 (3)	C17—C16—C21—C20	0.2 (3)
S1—C1—C6—C5	−179.88 (16)	S2—C16—C21—C20	179.10 (17)
S1—N1—C7—C8	−143.38 (19)	S2—N2—C22—C27	−168.06 (19)
S1—N1—C7—C12	38.0 (3)	S2—N2—C22—C23	12.9 (4)
C12—C7—C8—C9	0.6 (3)	C27—C22—C23—C24	−1.7 (4)
N1—C7—C8—C9	−178.1 (2)	N2—C22—C23—C24	177.3 (2)
C7—C8—C9—C10	−0.9 (4)	C22—C23—C24—C25	−0.1 (4)
C8—C9—C10—C11	0.7 (4)	C23—C24—C25—C26	1.7 (4)
C8—C9—C10—C15	−178.9 (3)	C23—C24—C25—C30	−177.8 (3)
C9—C10—C11—C12	−0.4 (4)	C24—C25—C26—C27	−1.5 (4)
C15—C10—C11—C12	179.2 (2)	C30—C25—C26—C27	178.0 (2)
C8—C7—C12—C11	−0.3 (3)	C23—C22—C27—C26	1.9 (4)
N1—C7—C12—C11	178.3 (2)	N2—C22—C27—C26	−177.2 (2)
C10—C11—C12—C7	0.2 (3)	C25—C26—C27—C22	−0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.85 (1)	2.15 (1)	2.991 (2)	169 (2)
N2—H2N···O2ii	0.85 (1)	2.03 (1)	2.877 (2)	175 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.85 (1)	2.15 (1)	2.991 (2)	169 (2)
N2—H2N⋯O2ii	0.85 (1)	2.03 (1)	2.877 (2)	175 (3)

Symmetry codes: (i) ; (ii) .