1-(4-Methoxy-phenyl-sulfon-yl)-5-methyl-5-phenyl-imidazolidine-2,4-dione.

The title compound, C(17)H(16)N(2)O(5)S, crystallized in the chiral monoclinic space group P2(1), with two enanti-omeric mol-ecules (A and B) in the asymmetric unit. It is composed of a methyl-imidazolidine-2,4-dione unit substituted with a phenyl group and a 4-methoxy-phenyl-sulfonyl group. The benzene ring mean planes are inclined to one another by 22.20 (14)° in mol-ecule A and by 15.82 (13)° in mol-ecule B. In the crystal structure, the A and B mol-ecules are linked by N-H⋯O hydrogen bonds, forming centrosymmetric dimers. A number of C-H⋯O inter-actions are also present in the crystal structure, leading to the formation of a three-dimensinoal network.

Related literature

For the applications of immidazolidine-2,4-diones, see: Thenmozhiyal et al. (2004 ▶); Zhang et al. (2004 ▶). For the activity of sulfonyl­immidazolidine-2,4-diones, see: Kashif, Ahmad & Hameed (2008 ▶); Ahmad et al. (2000 ▶, 2002 ▶); Murakami et al. (1997 ▶). For related crystal structures, see: Hussain et al. (2009 ▶); Kashif, Hussain et al. (2008 ▶).

Experimental

Crystal data

C17H16N2O5S

M = 360.38

Monoclinic,

a = 6.2314 (6) Å

b = 17.5694 (12) Å

c = 15.5892 (16) Å

β = 99.373 (12)°

V = 1683.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.38 × 0.30 × 0.19 mm

Data collection

Stoe IPDS diffractometer

Absorption correction: none

13521 measured reflections

6394 independent reflections

4309 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.058

S = 0.81

6394 reflections

465 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 2987 Friedel pairs

Flack parameter: 0.06 (5)

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000 ▶); cell refinement: CELL in IPDS-I; data reduction: INTEGRATE in IPDS-I; 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/S1600536809016092/bt2941sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016092/bt2941Isup2.hkl

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

C17H16N2O5S	F(000) = 752
Mr = 360.38	Dx = 1.421 Mg m−3
Monoclinic, P21	Melting point = 471–473 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 6.2314 (6) Å	Cell parameters from 8000 reflections
b = 17.5694 (12) Å	θ = 2.6–26.0°
c = 15.5892 (16) Å	µ = 0.22 mm−1
β = 99.373 (12)°	T = 173 K
V = 1683.9 (3) Å3	Rod, colourless
Z = 4	0.38 × 0.30 × 0.19 mm

Stoe IPDS diffractometer	4309 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 26.1°, θmin = 2.7°
φ rotation scans	h = −7→7
13521 measured reflections	k = −20→21
6394 independent reflections	l = −19→19

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.029	w = 1/[σ2(Fo2) + (0.024P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.058	(Δ/σ)max = 0.001
S = 0.81	Δρmax = 0.17 e Å−3
6394 reflections	Δρmin = −0.20 e Å−3
465 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraints	Extinction coefficient: 0.0042 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2987 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.06 (5)

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	0.49288 (9)	0.27479 (4)	0.41621 (4)	0.0322 (2)
O1	0.5317 (3)	0.19861 (10)	0.39102 (11)	0.0374 (6)
O2	0.6619 (3)	0.33014 (11)	0.42511 (11)	0.0414 (6)
O3	0.0791 (3)	0.20334 (11)	0.32063 (11)	0.0388 (6)
O4	−0.0034 (3)	0.43832 (11)	0.19756 (12)	0.0497 (7)
O5	0.0979 (3)	0.26824 (12)	0.73090 (12)	0.0622 (8)
N1	0.3022 (3)	0.30995 (11)	0.33861 (12)	0.0273 (7)
N2	−0.0122 (3)	0.31655 (12)	0.24927 (13)	0.0340 (8)
C1	0.1190 (4)	0.26883 (16)	0.30444 (15)	0.0299 (8)
C2	0.0728 (4)	0.38756 (16)	0.24475 (17)	0.0330 (9)
C3	0.2862 (4)	0.39125 (14)	0.30845 (15)	0.0285 (8)
C4	0.2584 (4)	0.44517 (15)	0.38246 (15)	0.0289 (8)
C5	0.0795 (4)	0.43753 (17)	0.42345 (17)	0.0409 (10)
C6	0.0477 (5)	0.48556 (18)	0.49017 (19)	0.0480 (10)
C7	0.1927 (5)	0.54235 (18)	0.51559 (19)	0.0519 (11)
C8	0.3705 (6)	0.55014 (19)	0.4763 (2)	0.0616 (11)
C9	0.4043 (5)	0.50230 (18)	0.40945 (18)	0.0483 (10)
C10	0.4663 (4)	0.41178 (16)	0.25751 (18)	0.0419 (10)
C11	0.3765 (4)	0.27369 (15)	0.51029 (15)	0.0303 (8)
C12	0.4167 (4)	0.33274 (15)	0.56842 (16)	0.0395 (9)
C13	0.3248 (5)	0.33334 (16)	0.64261 (17)	0.0447 (10)
C14	0.1936 (4)	0.27364 (18)	0.65885 (16)	0.0438 (10)
C15	0.1345 (7)	0.32823 (19)	0.7938 (2)	0.0826 (16)
C16	0.1511 (4)	0.21413 (17)	0.60013 (18)	0.0453 (10)
C17	0.2418 (4)	0.21460 (15)	0.52550 (16)	0.0360 (9)
S2	0.17941 (9)	0.16666 (4)	0.07688 (4)	0.0343 (2)
O6	0.1557 (3)	0.24522 (10)	0.09316 (11)	0.0443 (7)
O7	0.0040 (3)	0.11541 (11)	0.07948 (12)	0.0434 (6)
O8	0.5996 (3)	0.24274 (10)	0.16846 (11)	0.0382 (6)
O9	0.7248 (3)	0.00425 (10)	0.27716 (11)	0.0390 (6)
O10	0.5175 (3)	0.11964 (11)	−0.24698 (12)	0.0523 (7)
N3	0.3788 (3)	0.13476 (12)	0.15370 (13)	0.0285 (7)
N4	0.7059 (3)	0.12965 (12)	0.23550 (12)	0.0295 (7)
C18	0.5652 (4)	0.17648 (16)	0.18420 (15)	0.0290 (8)
C19	0.6295 (4)	0.05719 (16)	0.23806 (15)	0.0300 (8)
C20	0.4033 (4)	0.05427 (15)	0.18445 (15)	0.0286 (8)
C21	0.4028 (4)	−0.00248 (14)	0.10977 (15)	0.0284 (8)
C22	0.5752 (4)	−0.00181 (16)	0.06382 (15)	0.0354 (9)
C23	0.5797 (4)	−0.05236 (18)	−0.00387 (17)	0.0442 (10)
C24	0.4127 (5)	−0.10347 (16)	−0.02589 (17)	0.0466 (10)
C25	0.2398 (5)	−0.10367 (18)	0.01867 (19)	0.0488 (11)
C26	0.2350 (4)	−0.05315 (16)	0.08642 (17)	0.0390 (9)
C27	0.2452 (5)	0.03531 (17)	0.24687 (19)	0.0424 (10)
C28	0.2780 (4)	0.15486 (15)	−0.02036 (16)	0.0318 (8)
C29	0.1934 (4)	0.09875 (15)	−0.07862 (16)	0.0338 (8)
C30	0.2755 (4)	0.08912 (15)	−0.15410 (16)	0.0366 (9)
C31	0.4463 (4)	0.13473 (15)	−0.17102 (16)	0.0375 (9)
C32	0.6969 (5)	0.1640 (2)	−0.26728 (19)	0.0633 (13)
C33	0.5329 (4)	0.18981 (17)	−0.11248 (17)	0.0487 (10)
C34	0.4462 (4)	0.19955 (17)	−0.03783 (17)	0.0453 (10)
H2N	−0.143 (3)	0.2979 (16)	0.2234 (17)	0.057 (9)*
H5	−0.02360	0.39850	0.40540	0.0490*
H6	−0.07520	0.47900	0.51840	0.0580*
H7	0.16960	0.57630	0.56060	0.0620*
H8	0.47330	0.58910	0.49500	0.0740*
H9	0.52860	0.50890	0.38210	0.0580*
H10A	0.47220	0.37370	0.21200	0.0630*
H10B	0.60600	0.41290	0.29690	0.0630*
H10C	0.43690	0.46200	0.23070	0.0630*
H12	0.50880	0.37340	0.55720	0.0470*
H13	0.35120	0.37450	0.68240	0.0540*
H15A	0.29050	0.33220	0.81610	0.1240*
H15B	0.08230	0.37640	0.76630	0.1240*
H15C	0.05580	0.31710	0.84180	0.1240*
H16	0.05990	0.17330	0.61140	0.0540*
H17	0.21190	0.17440	0.48450	0.0430*
H4N	0.835 (3)	0.1490 (15)	0.2635 (16)	0.053 (9)*
H22	0.69070	0.03350	0.07890	0.0420*
H23	0.69830	−0.05180	−0.03520	0.0530*
H24	0.41700	−0.13860	−0.07190	0.0560*
H25	0.12350	−0.13850	0.00300	0.0590*
H26	0.11500	−0.05340	0.11700	0.0470*
H27A	0.09600	0.03590	0.21510	0.0640*
H27B	0.25970	0.07320	0.29360	0.0640*
H27C	0.27880	−0.01530	0.27190	0.0640*
H29	0.07880	0.06710	−0.06620	0.0410*
H30	0.21600	0.05140	−0.19480	0.0440*
H32A	0.82400	0.15630	−0.22210	0.0950*
H32B	0.65720	0.21800	−0.27000	0.0950*
H32C	0.73170	0.14780	−0.32360	0.0950*
H33	0.65070	0.22050	−0.12370	0.0580*
H34	0.50350	0.23790	0.00250	0.0540*

	U11	U22	U33	U12	U13	U23
S1	0.0318 (3)	0.0308 (4)	0.0350 (3)	0.0037 (3)	0.0081 (3)	0.0046 (3)
O1	0.0456 (10)	0.0279 (11)	0.0406 (10)	0.0154 (8)	0.0127 (8)	0.0030 (8)
O2	0.0309 (9)	0.0458 (13)	0.0475 (11)	−0.0090 (9)	0.0062 (8)	0.0103 (10)
O3	0.0469 (10)	0.0229 (12)	0.0444 (11)	−0.0020 (8)	0.0006 (8)	−0.0035 (9)
O4	0.0650 (12)	0.0332 (12)	0.0448 (11)	0.0118 (10)	−0.0093 (9)	0.0037 (10)
O5	0.0954 (15)	0.0495 (14)	0.0531 (12)	0.0007 (12)	0.0464 (11)	−0.0022 (11)
N1	0.0297 (10)	0.0221 (13)	0.0300 (11)	0.0007 (8)	0.0046 (9)	−0.0009 (9)
N2	0.0392 (13)	0.0240 (14)	0.0355 (12)	0.0028 (10)	−0.0037 (10)	−0.0047 (10)
C1	0.0356 (13)	0.0231 (16)	0.0305 (13)	0.0035 (13)	0.0038 (10)	−0.0040 (12)
C2	0.0422 (15)	0.0260 (17)	0.0308 (15)	0.0074 (12)	0.0060 (12)	−0.0041 (12)
C3	0.0352 (13)	0.0192 (15)	0.0315 (14)	0.0022 (10)	0.0068 (11)	0.0020 (11)
C4	0.0350 (13)	0.0224 (15)	0.0289 (13)	0.0001 (11)	0.0043 (11)	0.0009 (11)
C5	0.0381 (15)	0.0392 (19)	0.0462 (17)	−0.0060 (13)	0.0092 (13)	−0.0137 (14)
C6	0.0500 (17)	0.055 (2)	0.0410 (16)	0.0091 (15)	0.0136 (13)	−0.0104 (14)
C7	0.083 (2)	0.035 (2)	0.0374 (16)	0.0077 (16)	0.0091 (16)	−0.0062 (14)
C8	0.091 (2)	0.046 (2)	0.0474 (19)	−0.0311 (18)	0.0097 (18)	−0.0166 (16)
C9	0.0581 (17)	0.041 (2)	0.0479 (17)	−0.0172 (15)	0.0152 (14)	−0.0016 (15)
C10	0.0473 (16)	0.0388 (19)	0.0435 (16)	0.0055 (13)	0.0187 (13)	0.0089 (13)
C11	0.0329 (12)	0.0241 (15)	0.0346 (13)	−0.0004 (12)	0.0078 (10)	0.0022 (12)
C12	0.0529 (16)	0.0253 (17)	0.0408 (15)	−0.0063 (12)	0.0091 (13)	0.0031 (13)
C13	0.0721 (19)	0.0257 (17)	0.0390 (15)	−0.0021 (14)	0.0175 (14)	−0.0040 (12)
C14	0.0571 (17)	0.0390 (18)	0.0404 (15)	0.0067 (15)	0.0234 (13)	0.0032 (14)
C15	0.154 (4)	0.048 (2)	0.060 (2)	0.012 (2)	0.060 (2)	−0.0070 (18)
C16	0.0553 (17)	0.0359 (19)	0.0496 (17)	−0.0069 (13)	0.0235 (13)	−0.0008 (14)
C17	0.0407 (14)	0.0306 (17)	0.0384 (14)	−0.0018 (12)	0.0117 (11)	−0.0037 (12)
S2	0.0317 (3)	0.0336 (4)	0.0382 (4)	0.0030 (3)	0.0073 (3)	−0.0010 (3)
O6	0.0518 (11)	0.0318 (13)	0.0487 (11)	0.0145 (9)	0.0062 (9)	−0.0040 (9)
O7	0.0269 (9)	0.0545 (13)	0.0501 (11)	−0.0038 (9)	0.0101 (8)	0.0012 (10)
O8	0.0482 (10)	0.0232 (12)	0.0417 (11)	−0.0054 (8)	0.0026 (8)	−0.0007 (8)
O9	0.0500 (10)	0.0287 (12)	0.0367 (10)	0.0005 (9)	0.0024 (8)	0.0032 (9)
O10	0.0612 (12)	0.0570 (15)	0.0427 (11)	−0.0077 (10)	0.0202 (9)	−0.0060 (10)
N3	0.0325 (10)	0.0199 (13)	0.0335 (11)	−0.0013 (8)	0.0064 (9)	−0.0012 (9)
N4	0.0337 (12)	0.0226 (13)	0.0320 (12)	−0.0019 (10)	0.0050 (9)	−0.0015 (9)
C18	0.0330 (13)	0.0269 (17)	0.0284 (13)	0.0023 (12)	0.0085 (10)	−0.0048 (12)
C19	0.0430 (15)	0.0258 (16)	0.0231 (13)	−0.0004 (12)	0.0109 (11)	−0.0014 (11)
C20	0.0325 (13)	0.0228 (15)	0.0325 (14)	−0.0023 (10)	0.0114 (11)	−0.0041 (11)
C21	0.0323 (13)	0.0204 (15)	0.0324 (14)	−0.0014 (11)	0.0050 (11)	−0.0017 (11)
C22	0.0345 (13)	0.0394 (18)	0.0334 (14)	−0.0009 (12)	0.0090 (11)	−0.0068 (12)
C23	0.0547 (17)	0.0437 (19)	0.0353 (15)	0.0077 (15)	0.0105 (13)	−0.0057 (14)
C24	0.077 (2)	0.0272 (18)	0.0341 (15)	0.0070 (15)	0.0050 (15)	−0.0063 (13)
C25	0.0674 (19)	0.0307 (19)	0.0450 (17)	−0.0152 (14)	−0.0007 (15)	−0.0053 (14)
C26	0.0448 (15)	0.0308 (17)	0.0421 (16)	−0.0109 (13)	0.0088 (12)	−0.0017 (13)
C27	0.0479 (16)	0.0352 (19)	0.0494 (18)	−0.0030 (13)	0.0242 (14)	−0.0004 (13)
C28	0.0326 (12)	0.0291 (16)	0.0331 (13)	0.0000 (11)	0.0037 (10)	0.0007 (11)
C29	0.0328 (13)	0.0308 (16)	0.0371 (14)	−0.0056 (11)	0.0033 (11)	0.0006 (12)
C30	0.0426 (15)	0.0297 (17)	0.0360 (15)	−0.0056 (12)	0.0023 (12)	−0.0042 (12)
C31	0.0429 (14)	0.0403 (18)	0.0303 (14)	−0.0028 (13)	0.0088 (11)	0.0005 (12)
C32	0.0559 (18)	0.088 (3)	0.0501 (17)	−0.0130 (19)	0.0212 (14)	0.0026 (18)
C33	0.0520 (16)	0.055 (2)	0.0409 (16)	−0.0264 (14)	0.0131 (13)	−0.0059 (14)
C34	0.0553 (17)	0.0441 (19)	0.0362 (15)	−0.0192 (14)	0.0069 (13)	−0.0085 (13)

S1—O1	1.4266 (19)	C7—H7	0.9500
S1—O2	1.424 (2)	C8—H8	0.9500
S1—N1	1.670 (2)	C9—H9	0.9500
S1—C11	1.739 (2)	C10—H10B	0.9800
S2—N3	1.676 (2)	C10—H10A	0.9800
S2—O6	1.4155 (19)	C10—H10C	0.9800
S2—O7	1.422 (2)	C12—H12	0.9500
S2—C28	1.738 (3)	C13—H13	0.9500
O3—C1	1.212 (3)	C15—H15B	0.9800
O4—C2	1.203 (3)	C15—H15A	0.9800
O5—C14	1.358 (3)	C15—H15C	0.9800
O5—C15	1.432 (4)	C16—H16	0.9500
O8—C18	1.216 (3)	C17—H17	0.9500
O9—C19	1.213 (3)	C19—C20	1.518 (3)
O10—C31	1.357 (3)	C20—C27	1.530 (4)
O10—C32	1.440 (4)	C20—C21	1.532 (3)
N1—C1	1.382 (3)	C21—C22	1.385 (3)
N1—C3	1.502 (3)	C21—C26	1.376 (4)
N2—C1	1.372 (3)	C22—C23	1.383 (4)
N2—C2	1.362 (3)	C23—C24	1.375 (4)
N2—H2N	0.91 (2)	C24—C25	1.374 (4)
N3—C20	1.493 (3)	C25—C26	1.384 (4)
N3—C18	1.390 (3)	C28—C34	1.372 (4)
N4—C18	1.363 (3)	C28—C29	1.385 (4)
N4—C19	1.362 (3)	C29—C30	1.368 (4)
N4—H4N	0.92 (2)	C30—C31	1.391 (4)
C2—C3	1.526 (4)	C31—C33	1.378 (4)
C3—C4	1.524 (3)	C33—C34	1.371 (4)
C3—C10	1.520 (4)	C22—H22	0.9500
C4—C9	1.374 (4)	C23—H23	0.9500
C4—C5	1.379 (4)	C24—H24	0.9500
C5—C6	1.379 (4)	C25—H25	0.9500
C6—C7	1.361 (4)	C26—H26	0.9500
C7—C8	1.357 (5)	C27—H27A	0.9800
C8—C9	1.381 (4)	C27—H27B	0.9800
C11—C17	1.380 (4)	C27—H27C	0.9800
C11—C12	1.373 (4)	C29—H29	0.9500
C12—C13	1.372 (4)	C30—H30	0.9500
C13—C14	1.378 (4)	C32—H32A	0.9800
C14—C16	1.387 (4)	C32—H32B	0.9800
C16—C17	1.374 (4)	C32—H32C	0.9800
C5—H5	0.9500	C33—H33	0.9500
C6—H6	0.9500	C34—H34	0.9500
O1—S1—O2	120.78 (12)	C13—C12—H12	120.00
O1—S1—N1	106.27 (10)	C14—C13—H13	120.00
O1—S1—C11	109.54 (12)	C12—C13—H13	120.00
O2—S1—N1	104.23 (11)	O5—C15—H15B	109.00
O2—S1—C11	109.21 (12)	O5—C15—H15A	109.00
N1—S1—C11	105.65 (11)	H15A—C15—H15B	109.00
O7—S2—N3	104.59 (11)	H15A—C15—H15C	110.00
O7—S2—C28	109.38 (12)	O5—C15—H15C	109.00
N3—S2—C28	104.90 (11)	H15B—C15—H15C	110.00
O6—S2—C28	109.55 (12)	C14—C16—H16	120.00
O6—S2—O7	120.61 (12)	C17—C16—H16	120.00
O6—S2—N3	106.56 (11)	C16—C17—H17	120.00
C14—O5—C15	118.2 (2)	C11—C17—H17	120.00
C31—O10—C32	117.5 (2)	N3—C18—N4	107.7 (2)
S1—N1—C1	122.10 (17)	O8—C18—N3	126.9 (2)
S1—N1—C3	125.57 (16)	O8—C18—N4	125.4 (2)
C1—N1—C3	111.58 (19)	O9—C19—C20	125.8 (2)
C1—N2—C2	113.3 (2)	O9—C19—N4	125.9 (2)
C2—N2—H2N	129.4 (18)	N4—C19—C20	108.3 (2)
C1—N2—H2N	117.2 (18)	N3—C20—C21	112.64 (19)
S2—N3—C18	123.31 (18)	N3—C20—C19	100.5 (2)
S2—N3—C20	124.85 (16)	C19—C20—C27	107.1 (2)
C18—N3—C20	110.71 (19)	C21—C20—C27	114.8 (2)
C18—N4—C19	112.8 (2)	N3—C20—C27	111.6 (2)
C18—N4—H4N	119.1 (16)	C19—C20—C21	109.1 (2)
C19—N4—H4N	128.1 (16)	C22—C21—C26	119.3 (2)
N1—C1—N2	107.0 (2)	C20—C21—C22	118.8 (2)
O3—C1—N1	126.9 (2)	C20—C21—C26	122.0 (2)
O3—C1—N2	126.1 (2)	C21—C22—C23	120.2 (2)
O4—C2—C3	125.6 (2)	C22—C23—C24	120.1 (2)
O4—C2—N2	126.3 (2)	C23—C24—C25	120.0 (3)
N2—C2—C3	108.1 (2)	C24—C25—C26	120.0 (3)
N1—C3—C10	111.9 (2)	C21—C26—C25	120.5 (2)
N1—C3—C4	111.35 (19)	C29—C28—C34	119.9 (2)
N1—C3—C2	99.77 (19)	S2—C28—C29	120.4 (2)
C2—C3—C4	108.9 (2)	S2—C28—C34	119.7 (2)
C2—C3—C10	108.0 (2)	C28—C29—C30	119.8 (2)
C4—C3—C10	115.6 (2)	C29—C30—C31	119.8 (2)
C5—C4—C9	118.3 (2)	O10—C31—C33	124.5 (2)
C3—C4—C9	122.3 (2)	O10—C31—C30	115.0 (2)
C3—C4—C5	119.4 (2)	C30—C31—C33	120.5 (2)
C4—C5—C6	121.1 (3)	C31—C33—C34	118.9 (2)
C5—C6—C7	119.9 (3)	C28—C34—C33	121.1 (3)
C6—C7—C8	119.6 (3)	C21—C22—H22	120.00
C7—C8—C9	121.0 (3)	C23—C22—H22	120.00
C4—C9—C8	120.1 (3)	C22—C23—H23	120.00
S1—C11—C17	120.15 (19)	C24—C23—H23	120.00
S1—C11—C12	119.5 (2)	C23—C24—H24	120.00
C12—C11—C17	120.4 (2)	C25—C24—H24	120.00
C11—C12—C13	120.4 (2)	C24—C25—H25	120.00
C12—C13—C14	119.4 (3)	C26—C25—H25	120.00
O5—C14—C16	115.5 (3)	C21—C26—H26	120.00
C13—C14—C16	120.5 (2)	C25—C26—H26	120.00
O5—C14—C13	124.0 (3)	C20—C27—H27A	109.00
C14—C16—C17	119.6 (3)	C20—C27—H27B	110.00
C11—C17—C16	119.7 (2)	C20—C27—H27C	109.00
C4—C5—H5	119.00	H27A—C27—H27B	109.00
C6—C5—H5	119.00	H27A—C27—H27C	110.00
C5—C6—H6	120.00	H27B—C27—H27C	109.00
C7—C6—H6	120.00	C28—C29—H29	120.00
C6—C7—H7	120.00	C30—C29—H29	120.00
C8—C7—H7	120.00	C29—C30—H30	120.00
C7—C8—H8	120.00	C31—C30—H30	120.00
C9—C8—H8	119.00	O10—C32—H32A	109.00
C4—C9—H9	120.00	O10—C32—H32B	110.00
C8—C9—H9	120.00	O10—C32—H32C	109.00
H10A—C10—H10B	109.00	H32A—C32—H32B	109.00
H10A—C10—H10C	109.00	H32A—C32—H32C	109.00
C3—C10—H10C	109.00	H32B—C32—H32C	109.00
C3—C10—H10B	109.00	C31—C33—H33	121.00
C3—C10—H10A	110.00	C34—C33—H33	121.00
H10B—C10—H10C	110.00	C28—C34—H34	119.00
C11—C12—H12	120.00	C33—C34—H34	119.00
O1—S1—N1—C1	44.6 (2)	N2—C2—C3—N1	4.8 (2)
O1—S1—N1—C3	−146.18 (18)	O4—C2—C3—N1	−173.7 (2)
O2—S1—N1—C1	173.23 (18)	O4—C2—C3—C4	69.6 (3)
O2—S1—N1—C3	−17.6 (2)	O4—C2—C3—C10	−56.8 (3)
C11—S1—N1—C1	−71.7 (2)	C10—C3—C4—C9	−8.8 (4)
C11—S1—N1—C3	97.5 (2)	N1—C3—C4—C9	120.3 (3)
O1—S1—C11—C12	149.2 (2)	C2—C3—C4—C5	48.5 (3)
O1—S1—C11—C17	−31.9 (2)	N1—C3—C4—C5	−60.6 (3)
O2—S1—C11—C12	14.9 (2)	C10—C3—C4—C5	170.3 (2)
O2—S1—C11—C17	−166.3 (2)	C2—C3—C4—C9	−130.6 (3)
N1—S1—C11—C12	−96.7 (2)	C9—C4—C5—C6	−0.4 (4)
N1—S1—C11—C17	82.2 (2)	C3—C4—C5—C6	−179.5 (2)
O6—S2—N3—C18	−38.6 (2)	C3—C4—C9—C8	179.4 (3)
O6—S2—N3—C20	154.74 (18)	C5—C4—C9—C8	0.3 (4)
O7—S2—N3—C18	−167.37 (19)	C4—C5—C6—C7	1.0 (4)
O7—S2—N3—C20	26.0 (2)	C5—C6—C7—C8	−1.5 (5)
C28—S2—N3—C18	77.5 (2)	C6—C7—C8—C9	1.5 (5)
C28—S2—N3—C20	−89.1 (2)	C7—C8—C9—C4	−0.8 (5)
O6—S2—C28—C29	−137.8 (2)	S1—C11—C12—C13	179.4 (2)
O6—S2—C28—C34	44.6 (3)	C17—C11—C12—C13	0.5 (4)
O7—S2—C28—C29	−3.6 (3)	S1—C11—C17—C16	179.8 (2)
O7—S2—C28—C34	178.9 (2)	C12—C11—C17—C16	−1.4 (4)
N3—S2—C28—C29	108.1 (2)	C11—C12—C13—C14	0.8 (4)
N3—S2—C28—C34	−69.4 (2)	C12—C13—C14—O5	178.9 (3)
C15—O5—C14—C13	0.2 (4)	C12—C13—C14—C16	−1.2 (4)
C15—O5—C14—C16	−179.6 (3)	O5—C14—C16—C17	−179.7 (2)
C32—O10—C31—C30	−178.8 (2)	C13—C14—C16—C17	0.4 (4)
C32—O10—C31—C33	0.5 (4)	C14—C16—C17—C11	0.9 (4)
S1—N1—C3—C2	−175.22 (16)	O9—C19—C20—N3	−179.8 (2)
S1—N1—C1—O3	−5.0 (4)	O9—C19—C20—C21	−61.3 (3)
S1—N1—C1—N2	174.13 (15)	O9—C19—C20—C27	63.6 (3)
C3—N1—C1—O3	−175.6 (2)	N4—C19—C20—N3	0.9 (2)
C3—N1—C1—N2	3.6 (3)	N4—C19—C20—C21	119.4 (2)
C1—N1—C3—C2	−5.0 (2)	N4—C19—C20—C27	−115.8 (2)
S1—N1—C3—C4	−60.3 (3)	N3—C20—C21—C22	67.3 (3)
S1—N1—C3—C10	70.7 (2)	N3—C20—C21—C26	−111.8 (3)
C1—N1—C3—C4	109.9 (2)	C19—C20—C21—C22	−43.4 (3)
C1—N1—C3—C10	−119.1 (2)	C19—C20—C21—C26	137.6 (2)
C1—N2—C2—O4	175.3 (3)	C27—C20—C21—C22	−163.5 (2)
C2—N2—C1—O3	179.0 (2)	C27—C20—C21—C26	17.4 (3)
C2—N2—C1—N1	−0.2 (3)	C20—C21—C22—C23	179.9 (2)
C1—N2—C2—C3	−3.2 (3)	C26—C21—C22—C23	−1.0 (4)
S2—N3—C18—O8	9.1 (4)	C20—C21—C26—C25	−180.0 (3)
S2—N3—C18—N4	−170.73 (16)	C22—C21—C26—C25	1.0 (4)
C20—N3—C18—N4	−2.4 (3)	C21—C22—C23—C24	0.1 (4)
S2—N3—C20—C19	169.04 (16)	C22—C23—C24—C25	0.8 (4)
S2—N3—C20—C21	53.1 (3)	C23—C24—C25—C26	−0.9 (4)
S2—N3—C20—C27	−77.7 (2)	C24—C25—C26—C21	−0.1 (4)
C18—N3—C20—C19	0.9 (2)	S2—C28—C29—C30	−178.7 (2)
C18—N3—C20—C21	−115.0 (2)	C34—C28—C29—C30	−1.2 (4)
C18—N3—C20—C27	114.2 (2)	S2—C28—C34—C33	177.6 (2)
C20—N3—C18—O8	177.4 (2)	C29—C28—C34—C33	0.1 (4)
C19—N4—C18—N3	3.1 (3)	C28—C29—C30—C31	1.3 (4)
C18—N4—C19—O9	178.2 (2)	C29—C30—C31—O10	179.0 (2)
C18—N4—C19—C20	−2.5 (3)	C29—C30—C31—C33	−0.3 (4)
C19—N4—C18—O8	−176.8 (2)	O10—C31—C33—C34	180.0 (2)
N2—C2—C3—C4	−112.0 (2)	C30—C31—C33—C34	−0.8 (4)
N2—C2—C3—C10	121.7 (2)	C31—C33—C34—C28	0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O8i	0.91 (2)	1.95 (2)	2.851 (3)	171 (2)
N4—H4N···O3ii	0.92 (2)	1.89 (2)	2.800 (3)	171 (2)
C5—H5···O2i	0.95	2.36	3.218 (3)	150
C10—H10A···O8	0.98	2.56	3.437 (3)	149
C10—H10B···O2	0.98	2.45	3.055 (3)	120
C12—H12···O2	0.95	2.52	2.905 (3)	104
C13—H13···O9iii	0.95	2.43	3.287 (3)	150
C22—H22···O7ii	0.95	2.42	3.351 (3)	165
C24—H24···O8iv	0.95	2.56	3.492 (3)	166
C27—H27A···O7	0.98	2.52	3.126 (4)	120
C29—H29···O7	0.95	2.54	2.916 (3)	104
C30—H30···O4v	0.95	2.38	3.159 (3)	138
C34—H34···O8	0.95	2.56	3.291 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O8i	0.91 (2)	1.95 (2)	2.851 (3)	171 (2)
N4—H4N⋯O3ii	0.92 (2)	1.89 (2)	2.800 (3)	171 (2)
C5—H5⋯O2i	0.95	2.36	3.218 (3)	150
C10—H10A⋯O8	0.98	2.56	3.437 (3)	149
C10—H10B⋯O2	0.98	2.45	3.055 (3)	120
C12—H12⋯O2	0.95	2.52	2.905 (3)	104
C13—H13⋯O9iii	0.95	2.43	3.287 (3)	150
C22—H22⋯O7ii	0.95	2.42	3.351 (3)	165
C24—H24⋯O8iv	0.95	2.56	3.492 (3)	166
C27—H27A⋯O7	0.98	2.52	3.126 (4)	120
C29—H29⋯O7	0.95	2.54	2.916 (3)	104
C30—H30⋯O4v	0.95	2.38	3.159 (3)	138
C34—H34⋯O8	0.95	2.56	3.291 (3)	134

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