2-Methyl-N-(4-methyl-benzo-yl)benzene-sulfonamide.

The asymmetric unit of the title compound, C(15)H(15)NO(3)S, contains two independent mol-ecules. The conformations of the N-C bonds in the C-SO(2)-NH-C(O) segments have gauche torsions with respect to the SO bonds. Further, the mol-ecules are twisted at the S atoms with torsion angles of -53.1 (2) and 61.2 (2)° in the two mol-ecules. The dihedral angles between the sulfonyl benzene rings and the -SO(2)-NH-C-O segments are 86.0 (1) and 87.9 (1)°. Furthermore, the dihedral angles between the sulfonyl and the benzoyl benzene rings are 88.1 (1) and 83.5 (1)° in the two mol-ecules. In the crystal, mol-ecules are linked by N-H⋯O(S) hydrogen bonds.

Related literature

For background to our study of the effect of ring and the side-chain substituents on the crystal structures of N-aromatic sulfonamides and for similar structures, see: Gowda et al. (2009 ▶; 2010 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C15H15NO3S

M = 289.34

Triclinic,

a = 10.9085 (8) Å

b = 12.1392 (9) Å

c = 12.3140 (9) Å

α = 118.846 (8)°

β = 95.965 (6)°

γ = 90.136 (6)°

V = 1417.98 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 299 K

0.48 × 0.44 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD Detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.896, T max = 0.972

9669 measured reflections

5139 independent reflections

4302 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.105

S = 1.05

5139 reflections

371 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.34 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/S1600536810007440/bq2199sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007440/bq2199Isup2.hkl

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

C15H15NO3S	Z = 4
Mr = 289.34	F(000) = 608
Triclinic, P1	Dx = 1.355 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.9085 (8) Å	Cell parameters from 5092 reflections
b = 12.1392 (9) Å	θ = 2.5–27.9°
c = 12.3140 (9) Å	µ = 0.23 mm−1
α = 118.846 (8)°	T = 299 K
β = 95.965 (6)°	Plate, colourless
γ = 90.136 (6)°	0.48 × 0.44 × 0.12 mm
V = 1417.98 (18) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD Detector	5139 independent reflections
Radiation source: fine-focus sealed tube	4302 reflections with I > 2σ(I)
graphite	Rint = 0.013
Rotation method data acquisition using ω and phi scans	θmax = 25.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→13
Tmin = 0.896, Tmax = 0.972	k = −14→14
9669 measured reflections	l = −14→14

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0505P)2 + 0.5865P] where P = (Fo2 + 2Fc2)/3
5139 reflections	(Δ/σ)max = 0.020
371 parameters	Δρmax = 0.32 e Å−3
2 restraints	Δρmin = −0.34 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
S1	0.26147 (4)	0.15226 (4)	0.32500 (4)	0.03838 (13)
O1	0.18593 (13)	0.11786 (14)	0.39241 (14)	0.0545 (4)
O2	0.29413 (13)	0.05502 (12)	0.20811 (12)	0.0494 (4)
O3	0.19313 (14)	0.40481 (14)	0.48858 (12)	0.0534 (4)
N1	0.19457 (15)	0.25319 (14)	0.28899 (14)	0.0391 (4)
H1N	0.1743 (19)	0.2237 (19)	0.2135 (15)	0.047*
C1	0.39707 (17)	0.23373 (17)	0.42492 (17)	0.0390 (4)
C2	0.49086 (19)	0.2806 (2)	0.38683 (19)	0.0498 (5)
C3	0.5950 (2)	0.3360 (2)	0.4727 (2)	0.0669 (7)
H3	0.6600	0.3679	0.4507	0.080*
C4	0.6055 (2)	0.3455 (3)	0.5890 (2)	0.0717 (7)
H4	0.6770	0.3829	0.6439	0.086*
C5	0.5115 (2)	0.3006 (2)	0.6245 (2)	0.0653 (6)
H5	0.5187	0.3074	0.7035	0.078*
C6	0.4062 (2)	0.2453 (2)	0.54305 (18)	0.0487 (5)
H6	0.3412	0.2157	0.5671	0.058*
C7	0.16838 (17)	0.37305 (17)	0.37906 (16)	0.0381 (4)
C8	0.11559 (17)	0.45739 (16)	0.33317 (16)	0.0374 (4)
C9	0.07548 (18)	0.57174 (18)	0.42108 (19)	0.0453 (5)
H9	0.0799	0.5910	0.5043	0.054*
C10	0.0294 (2)	0.65630 (18)	0.3854 (2)	0.0524 (5)
H10	0.0013	0.7314	0.4448	0.063*
C11	0.0240 (2)	0.63239 (19)	0.2635 (2)	0.0528 (5)
C12	0.0645 (2)	0.5187 (2)	0.1765 (2)	0.0560 (6)
H12	0.0623	0.5010	0.0939	0.067*
C13	0.1078 (2)	0.43154 (18)	0.20990 (18)	0.0468 (5)
H13	0.1321	0.3548	0.1494	0.056*
C14	0.4853 (3)	0.2737 (3)	0.2615 (2)	0.0750 (8)
H14A	0.4184	0.3208	0.2521	0.090*
H14B	0.4724	0.1874	0.1971	0.090*
H14C	0.5616	0.3086	0.2552	0.090*
C15	−0.0234 (3)	0.7268 (2)	0.2253 (3)	0.0799 (8)
H15A	0.0410	0.7900	0.2455	0.096*
H15B	−0.0925	0.7657	0.2690	0.096*
H15C	−0.0489	0.6846	0.1369	0.096*
S2	0.86754 (5)	−0.02893 (4)	0.09718 (4)	0.03994 (14)
O4	0.82660 (15)	−0.14503 (12)	−0.01285 (12)	0.0534 (4)
O5	0.99533 (14)	−0.00545 (16)	0.13898 (14)	0.0603 (4)
O6	0.87360 (17)	0.24170 (13)	0.25506 (13)	0.0618 (4)
N2	0.81576 (16)	0.07925 (14)	0.06276 (14)	0.0394 (4)
H2N	0.7862 (19)	0.0503 (19)	−0.0110 (15)	0.047*
C16	0.78770 (19)	−0.01250 (16)	0.22121 (16)	0.0394 (4)
C17	0.6610 (2)	−0.04204 (19)	0.2040 (2)	0.0492 (5)
C18	0.6095 (3)	−0.0268 (2)	0.3090 (3)	0.0672 (7)
H18	0.5252	−0.0448	0.3021	0.081*
C19	0.6791 (3)	0.0136 (2)	0.4219 (2)	0.0740 (8)
H19	0.6416	0.0225	0.4899	0.089*
C20	0.8024 (3)	0.0410 (2)	0.4359 (2)	0.0670 (7)
H20	0.8491	0.0672	0.5128	0.080*
C21	0.8582 (2)	0.02962 (18)	0.33558 (18)	0.0504 (5)
H21	0.9422	0.0501	0.3448	0.060*
C22	0.82979 (18)	0.20707 (17)	0.14844 (17)	0.0410 (4)
C23	0.78477 (18)	0.29425 (17)	0.10290 (17)	0.0398 (4)
C24	0.7648 (2)	0.41595 (19)	0.1922 (2)	0.0531 (5)
H24	0.7803	0.4398	0.2766	0.064*
C25	0.7219 (2)	0.5015 (2)	0.1563 (2)	0.0610 (6)
H25	0.7076	0.5823	0.2173	0.073*
C26	0.6995 (2)	0.4704 (2)	0.0320 (2)	0.0567 (6)
C27	0.7227 (2)	0.3500 (2)	−0.0563 (2)	0.0609 (6)
H27	0.7106	0.3276	−0.1404	0.073*
C28	0.7637 (2)	0.26236 (19)	−0.02221 (19)	0.0513 (5)
H28	0.7772	0.1814	−0.0834	0.062*
C29	0.5796 (2)	−0.0874 (3)	0.0826 (2)	0.0685 (7)
H29A	0.5912	−0.0308	0.0502	0.082*
H29B	0.4949	−0.0901	0.0962	0.082*
H29C	0.6008	−0.1702	0.0238	0.082*
C30	0.6541 (3)	0.5661 (3)	−0.0056 (3)	0.0815 (8)
H30A	0.5804	0.5998	0.0317	0.098*
H30B	0.6365	0.5262	−0.0949	0.098*
H30C	0.7166	0.6331	0.0225	0.098*

	U11	U22	U33	U12	U13	U23
S1	0.0424 (3)	0.0321 (2)	0.0363 (2)	−0.00049 (18)	−0.00347 (19)	0.01476 (19)
O1	0.0526 (9)	0.0604 (9)	0.0576 (9)	−0.0133 (7)	−0.0069 (7)	0.0368 (8)
O2	0.0572 (9)	0.0328 (7)	0.0423 (7)	0.0068 (6)	−0.0058 (6)	0.0078 (6)
O3	0.0694 (10)	0.0543 (9)	0.0313 (7)	0.0173 (7)	0.0115 (6)	0.0156 (6)
N1	0.0493 (9)	0.0338 (8)	0.0276 (8)	0.0066 (7)	−0.0003 (7)	0.0106 (7)
C1	0.0397 (10)	0.0329 (9)	0.0374 (10)	0.0011 (7)	−0.0001 (8)	0.0123 (8)
C2	0.0490 (12)	0.0469 (11)	0.0472 (11)	−0.0026 (9)	0.0048 (9)	0.0182 (9)
C3	0.0514 (13)	0.0710 (16)	0.0677 (16)	−0.0165 (12)	−0.0002 (11)	0.0269 (13)
C4	0.0541 (14)	0.0795 (17)	0.0605 (15)	−0.0170 (12)	−0.0168 (12)	0.0221 (13)
C5	0.0617 (15)	0.0782 (17)	0.0444 (12)	−0.0048 (12)	−0.0100 (11)	0.0238 (12)
C6	0.0490 (12)	0.0526 (12)	0.0400 (11)	−0.0006 (9)	−0.0003 (9)	0.0201 (9)
C7	0.0394 (10)	0.0374 (10)	0.0324 (10)	0.0041 (8)	0.0083 (8)	0.0121 (8)
C8	0.0383 (10)	0.0315 (9)	0.0358 (9)	0.0022 (7)	0.0060 (7)	0.0108 (8)
C9	0.0480 (11)	0.0370 (10)	0.0410 (10)	0.0031 (8)	0.0119 (9)	0.0099 (8)
C10	0.0547 (12)	0.0299 (10)	0.0612 (14)	0.0085 (9)	0.0158 (10)	0.0113 (9)
C11	0.0576 (13)	0.0351 (10)	0.0616 (14)	0.0066 (9)	0.0018 (10)	0.0213 (10)
C12	0.0790 (16)	0.0432 (11)	0.0425 (11)	0.0102 (11)	0.0011 (11)	0.0192 (9)
C13	0.0642 (13)	0.0321 (10)	0.0360 (10)	0.0107 (9)	0.0056 (9)	0.0100 (8)
C14	0.0736 (17)	0.093 (2)	0.0635 (16)	−0.0173 (15)	0.0087 (13)	0.0424 (15)
C15	0.099 (2)	0.0528 (14)	0.089 (2)	0.0193 (14)	0.0012 (16)	0.0377 (14)
S2	0.0519 (3)	0.0363 (2)	0.0295 (2)	0.0112 (2)	0.00847 (19)	0.01357 (19)
O4	0.0870 (11)	0.0333 (7)	0.0325 (7)	0.0155 (7)	0.0102 (7)	0.0095 (6)
O5	0.0500 (9)	0.0811 (11)	0.0515 (9)	0.0161 (8)	0.0107 (7)	0.0325 (8)
O6	0.1017 (13)	0.0407 (8)	0.0329 (8)	−0.0081 (8)	−0.0062 (8)	0.0127 (6)
N2	0.0574 (10)	0.0313 (8)	0.0256 (7)	0.0011 (7)	0.0023 (7)	0.0112 (6)
C16	0.0574 (12)	0.0287 (9)	0.0347 (9)	0.0100 (8)	0.0114 (8)	0.0164 (8)
C17	0.0594 (13)	0.0407 (11)	0.0552 (12)	0.0117 (9)	0.0148 (10)	0.0277 (10)
C18	0.0759 (17)	0.0620 (15)	0.0802 (18)	0.0143 (12)	0.0339 (14)	0.0427 (14)
C19	0.117 (2)	0.0593 (15)	0.0607 (16)	0.0138 (15)	0.0431 (16)	0.0346 (13)
C20	0.113 (2)	0.0522 (13)	0.0367 (12)	0.0010 (14)	0.0115 (13)	0.0217 (10)
C21	0.0743 (15)	0.0393 (10)	0.0363 (10)	0.0023 (10)	0.0055 (10)	0.0176 (9)
C22	0.0527 (11)	0.0329 (9)	0.0318 (10)	−0.0041 (8)	0.0071 (8)	0.0110 (8)
C23	0.0464 (11)	0.0326 (9)	0.0383 (10)	−0.0030 (8)	0.0080 (8)	0.0151 (8)
C24	0.0708 (14)	0.0391 (11)	0.0442 (11)	0.0037 (10)	0.0172 (10)	0.0141 (9)
C25	0.0727 (16)	0.0378 (11)	0.0713 (16)	0.0128 (10)	0.0285 (13)	0.0216 (11)
C26	0.0493 (12)	0.0495 (12)	0.0794 (16)	0.0028 (10)	0.0068 (11)	0.0377 (12)
C27	0.0815 (17)	0.0501 (13)	0.0525 (13)	−0.0046 (11)	−0.0090 (12)	0.0293 (11)
C28	0.0741 (15)	0.0347 (10)	0.0398 (11)	−0.0019 (10)	−0.0001 (10)	0.0153 (9)
C29	0.0557 (14)	0.0772 (17)	0.0816 (18)	0.0049 (12)	0.0001 (12)	0.0473 (15)
C30	0.0750 (18)	0.0709 (17)	0.119 (2)	0.0144 (14)	0.0097 (16)	0.0620 (18)

S1—O1	1.4204 (15)	S2—O5	1.4131 (16)
S1—O2	1.4357 (14)	S2—O4	1.4318 (14)
S1—N1	1.6407 (16)	S2—N2	1.6474 (16)
S1—C1	1.7665 (18)	S2—C16	1.7648 (18)
O3—C7	1.209 (2)	O6—C22	1.210 (2)
N1—C7	1.393 (2)	N2—C22	1.389 (2)
N1—H1N	0.823 (15)	N2—H2N	0.826 (15)
C1—C6	1.385 (3)	C16—C21	1.384 (3)
C1—C2	1.394 (3)	C16—C17	1.395 (3)
C2—C3	1.386 (3)	C17—C18	1.395 (3)
C2—C14	1.500 (3)	C17—C29	1.501 (3)
C3—C4	1.372 (4)	C18—C19	1.368 (4)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.364 (4)	C19—C20	1.358 (4)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.372 (3)	C20—C21	1.381 (3)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.481 (3)	C22—C23	1.481 (3)
C8—C13	1.387 (3)	C23—C24	1.387 (3)
C8—C9	1.393 (2)	C23—C28	1.388 (3)
C9—C10	1.375 (3)	C24—C25	1.376 (3)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.379 (3)	C25—C26	1.382 (3)
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.386 (3)	C26—C27	1.381 (3)
C11—C15	1.508 (3)	C26—C30	1.511 (3)
C12—C13	1.376 (3)	C27—C28	1.379 (3)
C12—H12	0.9300	C27—H27	0.9300
C13—H13	0.9300	C28—H28	0.9300
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	118.37 (9)	O5—S2—O4	118.33 (9)
O1—S1—N1	110.91 (9)	O5—S2—N2	110.40 (9)
O2—S1—N1	103.89 (8)	O4—S2—N2	103.58 (8)
O1—S1—C1	108.05 (9)	O5—S2—C16	108.84 (9)
O2—S1—C1	109.46 (9)	O4—S2—C16	109.58 (9)
N1—S1—C1	105.41 (8)	N2—S2—C16	105.28 (8)
C7—N1—S1	122.55 (13)	C22—N2—S2	122.31 (13)
C7—N1—H1N	124.3 (15)	C22—N2—H2N	124.1 (15)
S1—N1—H1N	113.0 (15)	S2—N2—H2N	113.5 (15)
C6—C1—C2	121.80 (18)	C21—C16—C17	122.16 (19)
C6—C1—S1	115.72 (15)	C21—C16—S2	116.18 (16)
C2—C1—S1	122.45 (15)	C17—C16—S2	121.65 (15)
C3—C2—C1	116.1 (2)	C18—C17—C16	116.0 (2)
C3—C2—C14	119.5 (2)	C18—C17—C29	119.4 (2)
C1—C2—C14	124.38 (19)	C16—C17—C29	124.64 (19)
C4—C3—C2	122.3 (2)	C19—C18—C17	122.0 (3)
C4—C3—H3	118.9	C19—C18—H18	119.0
C2—C3—H3	118.9	C17—C18—H18	119.0
C5—C4—C3	120.4 (2)	C20—C19—C18	120.8 (2)
C5—C4—H4	119.8	C20—C19—H19	119.6
C3—C4—H4	119.8	C18—C19—H19	119.6
C4—C5—C6	119.6 (2)	C19—C20—C21	119.8 (2)
C4—C5—H5	120.2	C19—C20—H20	120.1
C6—C5—H5	120.2	C21—C20—H20	120.1
C5—C6—C1	119.8 (2)	C20—C21—C16	119.3 (2)
C5—C6—H6	120.1	C20—C21—H21	120.4
C1—C6—H6	120.1	C16—C21—H21	120.4
O3—C7—N1	119.72 (17)	O6—C22—N2	119.92 (17)
O3—C7—C8	123.46 (16)	O6—C22—C23	123.46 (17)
N1—C7—C8	116.76 (15)	N2—C22—C23	116.58 (16)
C13—C8—C9	118.46 (18)	C24—C23—C28	118.56 (19)
C13—C8—C7	124.17 (16)	C24—C23—C22	117.17 (17)
C9—C8—C7	117.33 (17)	C28—C23—C22	124.26 (17)
C10—C9—C8	120.27 (19)	C25—C24—C23	120.2 (2)
C10—C9—H9	119.9	C25—C24—H24	119.9
C8—C9—H9	119.9	C23—C24—H24	119.9
C9—C10—C11	121.55 (18)	C24—C25—C26	121.7 (2)
C9—C10—H10	119.2	C24—C25—H25	119.1
C11—C10—H10	119.2	C26—C25—H25	119.1
C10—C11—C12	117.92 (19)	C27—C26—C25	117.7 (2)
C10—C11—C15	121.4 (2)	C27—C26—C30	121.3 (2)
C12—C11—C15	120.6 (2)	C25—C26—C30	121.0 (2)
C13—C12—C11	121.3 (2)	C28—C27—C26	121.4 (2)
C13—C12—H12	119.3	C28—C27—H27	119.3
C11—C12—H12	119.3	C26—C27—H27	119.3
C12—C13—C8	120.41 (18)	C27—C28—C23	120.39 (19)
C12—C13—H13	119.8	C27—C28—H28	119.8
C8—C13—H13	119.8	C23—C28—H28	119.8
C2—C14—H14A	109.5	C17—C29—H29A	109.5
C2—C14—H14B	109.5	C17—C29—H29B	109.5
H14A—C14—H14B	109.5	H29A—C29—H29B	109.5
C2—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
C11—C15—H15A	109.5	C26—C30—H30A	109.5
C11—C15—H15B	109.5	C26—C30—H30B	109.5
H15A—C15—H15B	109.5	H30A—C30—H30B	109.5
C11—C15—H15C	109.5	C26—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	63.65 (17)	O5—S2—N2—C22	−56.08 (17)
O2—S1—N1—C7	−168.15 (15)	O4—S2—N2—C22	176.27 (15)
C1—S1—N1—C7	−53.06 (17)	C16—S2—N2—C22	61.22 (17)
O1—S1—C1—C6	1.77 (18)	O5—S2—C16—C21	5.46 (17)
O2—S1—C1—C6	−128.41 (15)	O4—S2—C16—C21	136.28 (15)
N1—S1—C1—C6	120.41 (15)	N2—S2—C16—C21	−112.89 (15)
O1—S1—C1—C2	−179.98 (16)	O5—S2—C16—C17	−173.72 (15)
O2—S1—C1—C2	49.84 (19)	O4—S2—C16—C17	−42.90 (17)
N1—S1—C1—C2	−61.34 (18)	N2—S2—C16—C17	67.92 (17)
C6—C1—C2—C3	1.8 (3)	C21—C16—C17—C18	−0.1 (3)
S1—C1—C2—C3	−176.38 (17)	S2—C16—C17—C18	178.99 (15)
C6—C1—C2—C14	−178.5 (2)	C21—C16—C17—C29	179.6 (2)
S1—C1—C2—C14	3.4 (3)	S2—C16—C17—C29	−1.2 (3)
C1—C2—C3—C4	−0.5 (4)	C16—C17—C18—C19	−0.5 (3)
C14—C2—C3—C4	179.7 (3)	C29—C17—C18—C19	179.7 (2)
C2—C3—C4—C5	−0.5 (4)	C17—C18—C19—C20	0.1 (4)
C3—C4—C5—C6	0.2 (4)	C18—C19—C20—C21	0.9 (4)
C4—C5—C6—C1	1.1 (4)	C19—C20—C21—C16	−1.5 (3)
C2—C1—C6—C5	−2.1 (3)	C17—C16—C21—C20	1.2 (3)
S1—C1—C6—C5	176.18 (18)	S2—C16—C21—C20	−178.02 (16)
S1—N1—C7—O3	−1.4 (3)	S2—N2—C22—O6	−5.3 (3)
S1—N1—C7—C8	175.96 (13)	S2—N2—C22—C23	176.83 (13)
O3—C7—C8—C13	167.5 (2)	O6—C22—C23—C24	−15.9 (3)
N1—C7—C8—C13	−9.7 (3)	N2—C22—C23—C24	161.89 (18)
O3—C7—C8—C9	−10.1 (3)	O6—C22—C23—C28	163.0 (2)
N1—C7—C8—C9	172.63 (17)	N2—C22—C23—C28	−19.2 (3)
C13—C8—C9—C10	0.0 (3)	C28—C23—C24—C25	1.6 (3)
C7—C8—C9—C10	177.76 (17)	C22—C23—C24—C25	−179.42 (19)
C8—C9—C10—C11	−1.5 (3)	C23—C24—C25—C26	−1.1 (4)
C9—C10—C11—C12	1.2 (3)	C24—C25—C26—C27	−0.6 (4)
C9—C10—C11—C15	−178.4 (2)	C24—C25—C26—C30	−179.1 (2)
C10—C11—C12—C13	0.6 (4)	C25—C26—C27—C28	1.8 (4)
C15—C11—C12—C13	−179.9 (2)	C30—C26—C27—C28	−179.7 (2)
C11—C12—C13—C8	−2.0 (3)	C26—C27—C28—C23	−1.2 (4)
C9—C8—C13—C12	1.7 (3)	C24—C23—C28—C27	−0.5 (3)
C7—C8—C13—C12	−175.89 (19)	C22—C23—C28—C27	−179.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4i	0.82 (2)	2.17 (2)	2.978 (2)	165 (2)
N2—H2N···O2i	0.83 (2)	2.20 (2)	3.022 (2)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4i	0.82 (2)	2.18 (2)	2.978 (2)	165 (2)
N2—H2N⋯O2i	0.83 (2)	2.20 (2)	3.022 (2)	171 (2)

Symmetry code: (i) .