A triclinic polymorph of N-[4-(4-methyl-benzene-sulfonamido)-phenyl-sulfon-yl]acetamide.

In the asymmetric unit of the title compound, C(15)H(16)N(2)O(5)S(2), there are two symmetry-independent mol-ecules which adopt similar conformations, with dihedral angles between the aromatic rings of 59.30 (8) and 61.81 (8)°, and dihedral angles between acetamide group and the benzene ring of 77.08 (10) and 78.40 (10)°. Each type of mol-ecule forms similar one-dimensional polymeric structures extending along the b axis via N-H⋯O hydrogen bonds. These hydrogen bonds generate two types of centrosymmetric motifs, R(2) (2)(8) and R(2) (2)(20). Moreover C-H⋯O inter-actions assemble the mol-ecules into a three-dimensional framework. The crystal structure was determined from a non-merohedral twin [ratio of the twin components = 0.322 (4):0.678 (4)].

Related literature

For a monoclinic polymorph of the title compound, see: Ashfaq et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H16N2O5S2

M = 368.42

Triclinic,

a = 9.6722 (3) Å

b = 11.9968 (4) Å

c = 15.4784 (6) Å

α = 82.802 (2)°

β = 79.232 (1)°

γ = 89.653 (2)°

V = 1750.24 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.35 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.915, T max = 0.938

31011 measured reflections

8382 independent reflections

5598 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.153

S = 1.02

8382 reflections

438 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008616/gk2456sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008616/gk2456Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008616/gk2456Isup3.cml

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

C15H16N2O5S2	Z = 4
Mr = 368.42	F(000) = 768
Triclinic, P1	Dx = 1.398 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6722 (3) Å	Cell parameters from 4587 reflections
b = 11.9968 (4) Å	θ = 1.7–25.0°
c = 15.4784 (6) Å	µ = 0.33 mm−1
α = 82.802 (2)°	T = 296 K
β = 79.232 (1)°	Prism, colorless
γ = 89.653 (2)°	0.35 × 0.25 × 0.22 mm
V = 1750.24 (11) Å3

Bruker Kappa APEXII CCD diffractometer	8382 independent reflections
Radiation source: fine-focus sealed tube	5598 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 7.60 pixels mm-1	θmax = 28.3°, θmin = 1.7°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.915, Tmax = 0.938	l = −20→20
31011 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0652P)2 + 0.7795P] where P = (Fo2 + 2Fc2)/3
8382 reflections	(Δ/σ)max = 0.001
438 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	1.18463 (8)	0.05657 (7)	0.15628 (5)	0.0535 (3)
S2	0.84421 (7)	0.35232 (5)	0.49521 (5)	0.0415 (2)
O1	1.2489 (3)	−0.0454 (2)	0.13292 (16)	0.0730 (9)
O2	1.2545 (2)	0.1621 (2)	0.12469 (15)	0.0698 (8)
O3	0.70702 (19)	0.30834 (16)	0.53244 (14)	0.0515 (7)
O4	0.8603 (2)	0.46483 (15)	0.44956 (14)	0.0523 (7)
O5	0.8812 (2)	0.18161 (16)	0.64458 (14)	0.0585 (7)
N1	1.1577 (3)	0.0404 (2)	0.26522 (15)	0.0494 (8)
N2	0.9331 (2)	0.35691 (18)	0.57571 (15)	0.0441 (7)
C1	1.0166 (3)	0.0638 (3)	0.12810 (18)	0.0500 (9)
C2	0.9520 (4)	0.1664 (3)	0.1181 (2)	0.0687 (12)
C3	0.8155 (4)	0.1685 (4)	0.1015 (3)	0.0785 (16)
C4	0.7443 (4)	0.0727 (4)	0.0942 (2)	0.0710 (14)
C5	0.8117 (4)	−0.0286 (4)	0.1023 (2)	0.0747 (14)
C6	0.9484 (4)	−0.0339 (3)	0.1193 (2)	0.0650 (12)
C7	0.5962 (4)	0.0779 (5)	0.0770 (3)	0.107 (2)
C8	1.0824 (3)	0.1175 (2)	0.31772 (17)	0.0423 (8)
C9	0.9745 (3)	0.0768 (2)	0.38598 (18)	0.0464 (9)
C10	0.9013 (3)	0.1481 (2)	0.44060 (19)	0.0450 (8)
C11	0.9352 (3)	0.2614 (2)	0.42570 (17)	0.0380 (8)
C12	1.0441 (3)	0.3032 (2)	0.35796 (19)	0.0516 (10)
C13	1.1186 (3)	0.2313 (2)	0.3047 (2)	0.0562 (10)
C14	0.9428 (3)	0.2699 (2)	0.64153 (18)	0.0447 (9)
C15	1.0310 (4)	0.2954 (3)	0.7061 (2)	0.0662 (12)
S3	0.69039 (8)	0.54642 (6)	0.15666 (5)	0.0506 (2)
S4	0.34505 (7)	0.15067 (5)	0.49579 (5)	0.0415 (2)
O6	0.7593 (2)	0.4488 (2)	0.12796 (15)	0.0663 (8)
O7	0.7553 (2)	0.65458 (19)	0.12984 (16)	0.0685 (8)
O8	0.3612 (2)	0.05275 (15)	0.45035 (14)	0.0517 (7)
O9	0.20777 (19)	0.18511 (16)	0.53232 (14)	0.0522 (7)
O10	0.3820 (2)	0.27238 (17)	0.64627 (14)	0.0581 (7)
N3	0.6647 (3)	0.53153 (19)	0.26533 (15)	0.0473 (8)
N4	0.4330 (2)	0.11853 (18)	0.57696 (15)	0.0435 (7)
C16	0.5211 (3)	0.5480 (3)	0.13051 (18)	0.0494 (9)
C17	0.4500 (4)	0.6488 (3)	0.1236 (2)	0.0664 (12)
C18	0.3142 (4)	0.6490 (4)	0.1090 (3)	0.0805 (16)
C19	0.2471 (4)	0.5512 (4)	0.1003 (2)	0.0774 (16)
C20	0.3210 (4)	0.4524 (4)	0.1049 (2)	0.0762 (14)
C21	0.4574 (4)	0.4491 (3)	0.1199 (2)	0.0630 (11)
C22	0.0974 (4)	0.5515 (6)	0.0856 (3)	0.121 (3)
C23	0.5887 (3)	0.4391 (2)	0.31887 (17)	0.0412 (8)
C24	0.6247 (3)	0.3287 (2)	0.3074 (2)	0.0533 (10)
C25	0.5486 (3)	0.2412 (2)	0.36048 (19)	0.0506 (9)
C26	0.4380 (3)	0.2630 (2)	0.42648 (17)	0.0389 (8)
C27	0.4030 (3)	0.3724 (2)	0.43997 (19)	0.0457 (8)
C28	0.4781 (3)	0.4596 (2)	0.38568 (18)	0.0452 (8)
C29	0.4428 (3)	0.1842 (2)	0.64282 (18)	0.0450 (9)
C30	0.5321 (4)	0.1372 (3)	0.7070 (2)	0.0655 (11)
H1	1.19113	−0.01807	0.29175	0.0592*
H2	0.99857	0.23250	0.12244	0.0824*
H2A	0.97704	0.41865	0.57684	0.0530*
H3	0.77109	0.23718	0.09504	0.0937*
H5	0.76554	−0.09420	0.09641	0.0899*
H6	0.99324	−0.10250	0.12462	0.0780*
H7A	0.58829	0.14113	0.03363	0.1594*
H7B	0.53193	0.08598	0.13109	0.1594*
H7C	0.57375	0.01005	0.05524	0.1594*
H9	0.95104	0.00057	0.39512	0.0557*
H10	0.82975	0.12018	0.48707	0.0540*
H12	1.06666	0.37953	0.34857	0.0619*
H13	1.19302	0.25870	0.26004	0.0675*
H15A	1.08342	0.23020	0.72170	0.0989*
H15B	0.97142	0.31599	0.75833	0.0989*
H15C	1.09487	0.35648	0.67974	0.0989*
H3A	0.69879	0.58185	0.29084	0.0568*
H4	0.47630	0.05569	0.57835	0.0522*
H17	0.49406	0.71564	0.12870	0.0796*
H18	0.26661	0.71646	0.10498	0.0965*
H20	0.27760	0.38609	0.09762	0.0914*
H21	0.50538	0.38172	0.12281	0.0753*
H22A	0.09375	0.52163	0.03134	0.1804*
H22B	0.06371	0.62703	0.08201	0.1804*
H22C	0.03928	0.50590	0.13413	0.1804*
H24	0.70038	0.31417	0.26384	0.0640*
H25	0.57139	0.16744	0.35203	0.0608*
H27	0.32961	0.38673	0.48515	0.0548*
H28	0.45444	0.53331	0.39387	0.0542*
H30A	0.47464	0.09206	0.75606	0.0981*
H30B	0.57526	0.19760	0.72820	0.0981*
H30C	0.60386	0.09164	0.67805	0.0981*

	U11	U22	U33	U12	U13	U23
S1	0.0472 (4)	0.0611 (5)	0.0493 (4)	0.0080 (3)	−0.0011 (3)	−0.0085 (3)
S2	0.0363 (3)	0.0328 (3)	0.0565 (4)	0.0002 (3)	−0.0108 (3)	−0.0063 (3)
O1	0.0676 (15)	0.0839 (17)	0.0679 (15)	0.0294 (13)	−0.0038 (12)	−0.0259 (12)
O2	0.0589 (14)	0.0778 (16)	0.0642 (14)	−0.0104 (12)	0.0028 (11)	0.0026 (12)
O3	0.0348 (10)	0.0470 (11)	0.0718 (13)	−0.0029 (8)	−0.0058 (9)	−0.0101 (9)
O4	0.0540 (12)	0.0328 (10)	0.0723 (13)	0.0028 (8)	−0.0208 (10)	−0.0016 (9)
O5	0.0577 (13)	0.0408 (11)	0.0734 (14)	−0.0052 (10)	−0.0097 (10)	0.0028 (10)
N1	0.0536 (14)	0.0459 (13)	0.0485 (13)	0.0113 (11)	−0.0110 (11)	−0.0038 (10)
N2	0.0470 (13)	0.0358 (11)	0.0512 (13)	−0.0061 (10)	−0.0130 (10)	−0.0056 (10)
C1	0.0504 (16)	0.0572 (18)	0.0418 (15)	0.0054 (14)	−0.0056 (12)	−0.0088 (13)
C2	0.073 (2)	0.063 (2)	0.078 (2)	0.0111 (18)	−0.0283 (19)	−0.0188 (17)
C3	0.075 (2)	0.085 (3)	0.086 (3)	0.030 (2)	−0.033 (2)	−0.026 (2)
C4	0.057 (2)	0.105 (3)	0.0506 (19)	0.001 (2)	−0.0073 (15)	−0.0122 (19)
C5	0.073 (2)	0.085 (3)	0.065 (2)	−0.024 (2)	−0.0119 (18)	−0.0052 (19)
C6	0.074 (2)	0.061 (2)	0.058 (2)	0.0000 (18)	−0.0095 (17)	−0.0041 (15)
C7	0.064 (3)	0.174 (5)	0.083 (3)	−0.001 (3)	−0.019 (2)	−0.014 (3)
C8	0.0442 (14)	0.0397 (14)	0.0443 (14)	0.0046 (11)	−0.0120 (11)	−0.0054 (11)
C9	0.0491 (16)	0.0327 (13)	0.0562 (17)	−0.0046 (12)	−0.0066 (13)	−0.0058 (12)
C10	0.0404 (14)	0.0388 (14)	0.0536 (16)	−0.0057 (11)	−0.0042 (12)	−0.0036 (12)
C11	0.0360 (13)	0.0313 (12)	0.0484 (15)	−0.0019 (10)	−0.0116 (11)	−0.0057 (10)
C12	0.0583 (18)	0.0345 (14)	0.0574 (18)	−0.0089 (13)	−0.0008 (14)	−0.0027 (12)
C13	0.0577 (18)	0.0446 (16)	0.0587 (18)	−0.0117 (14)	0.0060 (14)	−0.0016 (13)
C14	0.0380 (14)	0.0435 (15)	0.0500 (16)	0.0057 (12)	−0.0003 (12)	−0.0076 (12)
C15	0.067 (2)	0.075 (2)	0.059 (2)	−0.0006 (18)	−0.0183 (16)	−0.0083 (16)
S3	0.0428 (4)	0.0556 (4)	0.0502 (4)	−0.0075 (3)	−0.0006 (3)	−0.0061 (3)
S4	0.0370 (3)	0.0335 (3)	0.0558 (4)	0.0017 (3)	−0.0102 (3)	−0.0105 (3)
O6	0.0583 (13)	0.0745 (15)	0.0614 (14)	0.0071 (11)	0.0061 (10)	−0.0172 (11)
O7	0.0567 (13)	0.0655 (14)	0.0760 (15)	−0.0230 (11)	−0.0049 (11)	0.0085 (11)
O8	0.0558 (12)	0.0375 (10)	0.0670 (13)	0.0009 (9)	−0.0179 (10)	−0.0167 (9)
O9	0.0357 (10)	0.0473 (11)	0.0733 (14)	0.0022 (8)	−0.0071 (9)	−0.0108 (9)
O10	0.0561 (12)	0.0486 (12)	0.0730 (14)	0.0048 (10)	−0.0105 (10)	−0.0238 (10)
N3	0.0508 (14)	0.0434 (12)	0.0499 (13)	−0.0085 (10)	−0.0123 (10)	−0.0094 (10)
N4	0.0463 (12)	0.0333 (11)	0.0522 (13)	0.0067 (10)	−0.0115 (10)	−0.0075 (9)
C16	0.0480 (16)	0.0589 (18)	0.0405 (15)	−0.0075 (14)	−0.0046 (12)	−0.0086 (12)
C17	0.065 (2)	0.067 (2)	0.073 (2)	0.0022 (18)	−0.0188 (17)	−0.0230 (17)
C18	0.064 (2)	0.106 (3)	0.080 (3)	0.019 (2)	−0.0204 (19)	−0.035 (2)
C19	0.0507 (19)	0.136 (4)	0.0482 (19)	−0.011 (2)	−0.0060 (15)	−0.026 (2)
C20	0.074 (2)	0.098 (3)	0.056 (2)	−0.042 (2)	−0.0102 (18)	−0.0086 (19)
C21	0.069 (2)	0.065 (2)	0.0556 (19)	−0.0159 (17)	−0.0133 (16)	−0.0063 (15)
C22	0.057 (2)	0.232 (7)	0.084 (3)	−0.010 (3)	−0.017 (2)	−0.058 (4)
C23	0.0421 (14)	0.0379 (13)	0.0457 (15)	0.0003 (11)	−0.0125 (11)	−0.0075 (11)
C24	0.0525 (17)	0.0449 (16)	0.0581 (18)	0.0098 (13)	0.0056 (14)	−0.0136 (13)
C25	0.0606 (18)	0.0347 (14)	0.0553 (17)	0.0108 (13)	−0.0033 (14)	−0.0128 (12)
C26	0.0360 (13)	0.0343 (13)	0.0486 (15)	0.0025 (10)	−0.0110 (11)	−0.0093 (11)
C27	0.0389 (14)	0.0419 (14)	0.0550 (16)	0.0079 (12)	−0.0007 (12)	−0.0139 (12)
C28	0.0471 (15)	0.0337 (13)	0.0550 (16)	0.0065 (11)	−0.0063 (12)	−0.0121 (11)
C29	0.0403 (14)	0.0422 (15)	0.0499 (16)	−0.0041 (12)	−0.0003 (12)	−0.0084 (12)
C30	0.067 (2)	0.078 (2)	0.0555 (19)	0.0052 (18)	−0.0188 (16)	−0.0127 (16)

S1—O1	1.425 (3)	C3—H3	0.9300
S1—O2	1.425 (2)	C5—H5	0.9300
S1—N1	1.644 (2)	C6—H6	0.9300
S1—C1	1.759 (3)	C7—H7A	0.9600
S2—O3	1.421 (2)	C7—H7B	0.9600
S2—O4	1.438 (2)	C7—H7C	0.9600
S2—N2	1.647 (2)	C9—H9	0.9300
S2—C11	1.747 (3)	C10—H10	0.9300
S3—O7	1.424 (2)	C12—H12	0.9300
S3—N3	1.641 (2)	C13—H13	0.9300
S3—O6	1.423 (2)	C15—H15C	0.9600
S3—C16	1.758 (3)	C15—H15B	0.9600
S4—O9	1.423 (2)	C15—H15A	0.9600
S4—N4	1.651 (2)	C16—C17	1.390 (5)
S4—O8	1.436 (2)	C16—C21	1.382 (5)
S4—C26	1.751 (3)	C17—C18	1.374 (6)
O5—C14	1.210 (3)	C18—C19	1.378 (7)
O10—C29	1.209 (3)	C19—C20	1.382 (6)
N1—C8	1.416 (4)	C19—C22	1.507 (6)
N2—C14	1.380 (3)	C20—C21	1.381 (6)
N1—H1	0.8600	C23—C28	1.386 (4)
N2—H2A	0.8600	C23—C24	1.392 (3)
N3—C23	1.417 (4)	C24—C25	1.373 (4)
N4—C29	1.381 (3)	C25—C26	1.383 (4)
N3—H3A	0.8600	C26—C27	1.385 (3)
N4—H4	0.8600	C27—C28	1.374 (4)
C1—C6	1.382 (5)	C29—C30	1.492 (5)
C1—C2	1.382 (5)	C17—H17	0.9300
C2—C3	1.391 (6)	C18—H18	0.9300
C3—C4	1.371 (6)	C20—H20	0.9300
C4—C5	1.379 (7)	C21—H21	0.9300
C4—C7	1.505 (6)	C22—H22A	0.9600
C5—C6	1.395 (5)	C22—H22B	0.9600
C8—C13	1.392 (3)	C22—H22C	0.9600
C8—C9	1.382 (4)	C24—H24	0.9300
C9—C10	1.378 (4)	C25—H25	0.9300
C10—C11	1.381 (3)	C27—H27	0.9300
C11—C12	1.387 (4)	C28—H28	0.9300
C12—C13	1.375 (4)	C30—H30A	0.9600
C14—C15	1.490 (5)	C30—H30B	0.9600
C2—H2	0.9300	C30—H30C	0.9600
O1—S1—O2	120.70 (15)	C4—C7—H7B	110.00
O1—S1—N1	104.06 (14)	C4—C7—H7C	110.00
O1—S1—C1	109.20 (17)	C4—C7—H7A	109.00
O2—S1—N1	108.23 (14)	H7B—C7—H7C	109.00
O2—S1—C1	107.86 (15)	C8—C9—H9	120.00
N1—S1—C1	105.84 (14)	C10—C9—H9	120.00
O3—S2—O4	119.35 (12)	C11—C10—H10	120.00
O3—S2—N2	108.69 (12)	C9—C10—H10	120.00
O3—S2—C11	110.10 (13)	C13—C12—H12	120.00
O4—S2—N2	103.10 (12)	C11—C12—H12	120.00
O4—S2—C11	108.62 (12)	C8—C13—H13	120.00
N2—S2—C11	106.04 (12)	C12—C13—H13	120.00
N3—S3—C16	105.24 (14)	C14—C15—H15C	109.00
O7—S3—C16	109.50 (15)	H15B—C15—H15C	110.00
O6—S3—N3	107.70 (13)	C14—C15—H15A	109.00
O6—S3—C16	108.13 (15)	H15A—C15—H15B	110.00
O6—S3—O7	120.60 (14)	H15A—C15—H15C	110.00
O7—S3—N3	104.61 (14)	C14—C15—H15B	109.00
O8—S4—C26	108.63 (12)	S3—C16—C17	119.5 (3)
O9—S4—N4	108.81 (12)	S3—C16—C21	120.2 (3)
O8—S4—N4	102.93 (12)	C17—C16—C21	120.3 (3)
O8—S4—O9	119.59 (12)	C16—C17—C18	119.6 (4)
O9—S4—C26	109.97 (13)	C17—C18—C19	121.3 (4)
N4—S4—C26	105.93 (12)	C18—C19—C22	121.2 (5)
S1—N1—C8	123.5 (2)	C20—C19—C22	120.6 (5)
S2—N2—C14	125.40 (18)	C18—C19—C20	118.2 (4)
C8—N1—H1	118.00	C19—C20—C21	122.0 (4)
S1—N1—H1	118.00	C16—C21—C20	118.6 (4)
S2—N2—H2A	117.00	C24—C23—C28	119.4 (2)
C14—N2—H2A	117.00	N3—C23—C24	121.6 (2)
S3—N3—C23	122.68 (19)	N3—C23—C28	119.0 (2)
S4—N4—C29	125.40 (18)	C23—C24—C25	120.0 (3)
C23—N3—H3A	119.00	C24—C25—C26	119.9 (2)
S3—N3—H3A	119.00	S4—C26—C25	119.41 (19)
C29—N4—H4	117.00	S4—C26—C27	119.8 (2)
S4—N4—H4	117.00	C25—C26—C27	120.7 (2)
C2—C1—C6	120.6 (3)	C26—C27—C28	119.1 (3)
S1—C1—C6	119.6 (3)	C23—C28—C27	120.8 (2)
S1—C1—C2	119.8 (3)	O10—C29—C30	124.3 (3)
C1—C2—C3	118.4 (4)	N4—C29—C30	114.7 (2)
C2—C3—C4	122.2 (4)	O10—C29—N4	121.0 (3)
C3—C4—C5	118.6 (4)	C16—C17—H17	120.00
C5—C4—C7	120.6 (4)	C18—C17—H17	120.00
C3—C4—C7	120.8 (4)	C17—C18—H18	119.00
C4—C5—C6	120.8 (4)	C19—C18—H18	119.00
C1—C6—C5	119.4 (4)	C19—C20—H20	119.00
C9—C8—C13	119.7 (2)	C21—C20—H20	119.00
N1—C8—C13	121.7 (3)	C16—C21—H21	121.00
N1—C8—C9	118.5 (2)	C20—C21—H21	121.00
C8—C9—C10	120.6 (2)	C19—C22—H22A	109.00
C9—C10—C11	119.4 (3)	C19—C22—H22B	110.00
S2—C11—C12	119.58 (19)	C19—C22—H22C	109.00
S2—C11—C10	119.7 (2)	H22A—C22—H22B	109.00
C10—C11—C12	120.6 (2)	H22A—C22—H22C	109.00
C11—C12—C13	119.7 (2)	H22B—C22—H22C	109.00
C8—C13—C12	119.9 (3)	C23—C24—H24	120.00
N2—C14—C15	114.8 (2)	C25—C24—H24	120.00
O5—C14—C15	124.7 (3)	C24—C25—H25	120.00
O5—C14—N2	120.5 (3)	C26—C25—H25	120.00
C1—C2—H2	121.00	C26—C27—H27	120.00
C3—C2—H2	121.00	C28—C27—H27	120.00
C4—C3—H3	119.00	C23—C28—H28	120.00
C2—C3—H3	119.00	C27—C28—H28	120.00
C4—C5—H5	120.00	C29—C30—H30A	109.00
C6—C5—H5	120.00	C29—C30—H30B	109.00
C1—C6—H6	120.00	C29—C30—H30C	109.00
C5—C6—H6	120.00	H30A—C30—H30B	109.00
H7A—C7—H7C	109.00	H30A—C30—H30C	109.00
H7A—C7—H7B	109.00	H30B—C30—H30C	109.00
O1—S1—N1—C8	−173.5 (3)	S4—N4—C29—O10	1.7 (4)
O2—S1—N1—C8	57.0 (3)	S4—N4—C29—C30	−178.4 (2)
C1—S1—N1—C8	−58.4 (3)	C2—C1—C6—C5	−1.6 (4)
O1—S1—C1—C2	−159.9 (2)	S1—C1—C2—C3	−175.9 (3)
O1—S1—C1—C6	22.5 (3)	C6—C1—C2—C3	1.8 (5)
O2—S1—C1—C2	−27.0 (3)	S1—C1—C6—C5	176.1 (2)
O2—S1—C1—C6	155.3 (2)	C1—C2—C3—C4	−0.5 (6)
N1—S1—C1—C2	88.7 (3)	C2—C3—C4—C5	−1.0 (6)
N1—S1—C1—C6	−89.0 (3)	C2—C3—C4—C7	179.5 (4)
O3—S2—N2—C14	48.6 (2)	C7—C4—C5—C6	−179.2 (3)
O4—S2—N2—C14	176.2 (2)	C3—C4—C5—C6	1.3 (5)
C11—S2—N2—C14	−69.7 (2)	C4—C5—C6—C1	0.0 (5)
O3—S2—C11—C10	−27.0 (3)	N1—C8—C13—C12	−179.1 (3)
O3—S2—C11—C12	155.3 (2)	C13—C8—C9—C10	0.8 (4)
O4—S2—C11—C10	−159.3 (2)	N1—C8—C9—C10	177.9 (3)
O4—S2—C11—C12	22.9 (3)	C9—C8—C13—C12	−2.0 (4)
N2—S2—C11—C10	90.4 (3)	C8—C9—C10—C11	1.0 (4)
N2—S2—C11—C12	−87.3 (2)	C9—C10—C11—S2	−179.4 (2)
N3—S3—C16—C17	86.6 (3)	C9—C10—C11—C12	−1.6 (4)
N3—S3—C16—C21	−91.3 (3)	S2—C11—C12—C13	178.2 (2)
O6—S3—N3—C23	−57.2 (3)	C10—C11—C12—C13	0.4 (4)
O7—S3—N3—C23	173.4 (2)	C11—C12—C13—C8	1.4 (4)
C16—S3—N3—C23	58.0 (3)	S3—C16—C17—C18	−175.7 (3)
O6—S3—C16—C17	−158.6 (2)	C21—C16—C17—C18	2.1 (5)
O6—S3—C16—C21	23.6 (3)	S3—C16—C21—C20	176.0 (2)
O7—S3—C16—C17	−25.4 (3)	C17—C16—C21—C20	−1.8 (4)
O7—S3—C16—C21	156.8 (2)	C16—C17—C18—C19	−0.5 (6)
O8—S4—N4—C29	−176.4 (2)	C17—C18—C19—C20	−1.3 (6)
O9—S4—N4—C29	−48.6 (2)	C17—C18—C19—C22	179.1 (4)
C26—S4—N4—C29	69.6 (2)	C18—C19—C20—C21	1.6 (5)
O8—S4—C26—C25	−23.8 (3)	C22—C19—C20—C21	−178.8 (3)
O8—S4—C26—C27	158.2 (2)	C19—C20—C21—C16	0.0 (5)
O9—S4—C26—C25	−156.4 (2)	N3—C23—C24—C25	−180.0 (3)
O9—S4—C26—C27	25.6 (3)	C28—C23—C24—C25	1.7 (4)
N4—S4—C26—C25	86.2 (2)	N3—C23—C28—C27	−179.0 (3)
N4—S4—C26—C27	−91.9 (2)	C24—C23—C28—C27	−0.6 (4)
S1—N1—C8—C9	128.8 (3)	C23—C24—C25—C26	−1.3 (4)
S1—N1—C8—C13	−54.2 (4)	C24—C25—C26—S4	−178.2 (2)
S2—N2—C14—C15	179.5 (2)	C24—C25—C26—C27	−0.2 (4)
S2—N2—C14—O5	−1.4 (4)	S4—C26—C27—C28	179.2 (2)
S3—N3—C23—C28	−127.2 (3)	C25—C26—C27—C28	1.2 (4)
S3—N3—C23—C24	54.5 (4)	C26—C27—C28—C23	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5i	0.86	2.14	2.841 (3)	138
N2—H2A···O4ii	0.86	2.06	2.876 (3)	158
N3—H3A···O10iii	0.86	2.18	2.859 (3)	136
N4—H4···O8iv	0.86	2.05	2.867 (3)	157
C13—H13···O2	0.93	2.49	3.062 (4)	120
C22—H22A···O6v	0.96	2.59	3.338 (5)	135
C24—H24···O6	0.93	2.46	3.026 (4)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5i	0.86	2.14	2.841 (3)	138
N2—H2A⋯O4ii	0.86	2.06	2.876 (3)	158
N3—H3A⋯O10iii	0.86	2.18	2.859 (3)	136
N4—H4⋯O8iv	0.86	2.05	2.867 (3)	157
C13—H13⋯O2	0.93	2.49	3.062 (4)	120
C22—H22A⋯O6v	0.96	2.59	3.338 (5)	135
C24—H24⋯O6	0.93	2.46	3.026 (4)	119

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