1-(4-Chloro-phenyl-sulfon-yl)-5-(4-fluoro-phen-yl)-5-methyl-imidazolidine-2,4-dione.

The title compound, C(16)H(12)ClFN(2)O(4)S, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. The two mol-ecules are U-shaped with similar geometries and conformations. The mean planes through the benzene rings are inclined to one another by 6.07 (8)° in mol-ecule A and 8.67 (8)° in mol-ecule B. They are separated with a centroid-centroid distance of 3.9096 (10) Å in mol-ecule A and 3.9118 (10) Å in mol-ecule B. Mol-ecules A and B lie adjacent to one another, with a centroid-centroid distance of 3.7592 (10) Å between the fluoro-phenyl ring of mol-ecule A and the chloro-phenyl-sulfonyl ring of mol-ecule B and with a dihedral angle of 5.75 (8)° between the ring planes. In the crystal structure, A and B mol-ecules are linked by N-H⋯O hydrogen bonds, forming centrosymmetric dimers. These dimers stack along the [110] direction and are linked by C-H⋯O and C-H⋯F inter-actions. There are also some short halide⋯halide contacts [Cl⋯F = 3.0499 (14) and 3.1224 (13) Å, and F⋯F = 3.0612 (17) Å].

Related literature

For the biological activity of imidazolidine-2,4-diones, see: Muccioli et al. (2006 ▶); Flosi et al. (2006 ▶). For the biological activity of sulfonyl derivatives of imidazolidine-2,4-diones, see: Kato, Nakayama, Mizota et al. (1991 ▶); Kato, Nakayama, Ohta et al. (1991 ▶); Ahmad et al. (2000 ▶, 2002 ▶); Kashif, Ahmad & Hameed (2008 ▶). For the crystal structure of 5-(4-fluoro­phen­yl)-5-methyl­imidazolidine-2,4-dione, see: Kashif, Hussain et al. (2008 ▶).

Experimental

Crystal data

C16H12ClFN2O4S

M = 382.79

Triclinic,

a = 9.6959 (7) Å

b = 10.0066 (7) Å

c = 16.6269 (13) Å

α = 92.098 (6)°

β = 93.630 (6)°

γ = 103.056 (6)°

V = 1566.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 173 K

0.45 × 0.40 × 0.24 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: none

30542 measured reflections

8438 independent reflections

5836 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.095

S = 0.89

8438 reflections

462 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.64 e Å−3

Data collection: X-AREA (Stoe & Cie, 2006 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2006 ▶); 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/S160053680901037X/nc2138sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901037X/nc2138Isup2.hkl

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

C16H12ClFN2O4S	Z = 4
Mr = 382.79	F(000) = 784
Triclinic, P1	Dx = 1.623 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6959 (7) Å	Cell parameters from 20500 reflections
b = 10.0066 (7) Å	θ = 2.1–29.5°
c = 16.6269 (13) Å	µ = 0.41 mm−1
α = 92.098 (6)°	T = 173 K
β = 93.630 (6)°	Plate, colourless
γ = 103.056 (6)°	0.45 × 0.40 × 0.24 mm
V = 1566.2 (2) Å3

Stoe IPDS-2 diffractometer	5836 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
graphite	θmax = 29.3°, θmin = 2.1°
φ and ω scans	h = −13→12
30542 measured reflections	k = −13→13
8438 independent reflections	l = −22→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0594P)2] where P = (Fo2 + 2Fc2)/3
S = 0.89	(Δ/σ)max = 0.001
8438 reflections	Δρmax = 0.49 e Å−3
462 parameters	Δρmin = −0.64 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0070 (7)

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
Cl1	0.91764 (7)	−0.33306 (8)	0.44481 (3)	0.0678 (2)
S1	1.07493 (4)	0.03707 (4)	0.15675 (2)	0.0216 (1)
F1	0.74943 (12)	0.11810 (12)	0.46455 (6)	0.0435 (4)
O1	0.88878 (13)	−0.18444 (11)	0.04068 (7)	0.0292 (3)
O2	0.57120 (12)	0.08199 (11)	0.07970 (6)	0.0266 (3)
O3	1.12161 (12)	0.17630 (11)	0.18656 (8)	0.0317 (3)
O4	1.15471 (12)	−0.02016 (12)	0.10155 (7)	0.0306 (3)
N1	0.91377 (13)	0.02536 (12)	0.11173 (7)	0.0188 (3)
N2	0.70525 (14)	−0.07265 (13)	0.04699 (7)	0.0217 (4)
C1	1.04515 (16)	−0.06802 (16)	0.23943 (9)	0.0239 (4)
C2	1.06304 (19)	−0.00804 (19)	0.31679 (10)	0.0324 (5)
C3	1.0280 (2)	−0.0905 (2)	0.38108 (10)	0.0412 (6)
C4	0.9731 (2)	−0.2300 (2)	0.36571 (11)	0.0399 (6)
C5	0.95939 (19)	−0.29070 (19)	0.28916 (11)	0.0350 (5)
C6	0.99744 (17)	−0.20954 (16)	0.22461 (10)	0.0271 (5)
C7	0.84130 (17)	−0.08949 (14)	0.06303 (8)	0.0211 (4)
C8	0.68087 (16)	0.04368 (14)	0.08337 (8)	0.0192 (4)
C9	0.81941 (15)	0.11962 (13)	0.13079 (8)	0.0175 (4)
C10	0.86819 (16)	0.25816 (14)	0.09386 (9)	0.0227 (4)
C11	0.79666 (15)	0.12483 (14)	0.22069 (8)	0.0180 (4)
C12	0.84186 (16)	0.24448 (15)	0.26969 (9)	0.0230 (4)
C13	0.82563 (18)	0.24327 (17)	0.35230 (9)	0.0287 (5)
C14	0.76299 (18)	0.12121 (18)	0.38395 (9)	0.0282 (5)
C15	0.71357 (17)	0.00078 (16)	0.33735 (9)	0.0264 (4)
C16	0.73163 (16)	0.00364 (15)	0.25529 (8)	0.0221 (4)
Cl2	0.40511 (6)	0.12790 (6)	0.43991 (3)	0.0533 (2)
S2	0.58277 (4)	0.54282 (4)	0.17383 (2)	0.0238 (1)
F2	0.23250 (13)	0.58675 (13)	0.47233 (6)	0.0462 (4)
O5	0.41852 (14)	0.33765 (12)	0.04019 (7)	0.0323 (4)
O6	0.08075 (12)	0.57818 (11)	0.08571 (6)	0.0268 (3)
O7	0.62142 (12)	0.67806 (11)	0.21087 (8)	0.0329 (4)
O8	0.67356 (13)	0.49688 (12)	0.12089 (8)	0.0349 (4)
N3	0.42774 (14)	0.53320 (12)	0.12274 (7)	0.0207 (4)
N4	0.22860 (15)	0.43999 (13)	0.04734 (7)	0.0245 (4)
C17	0.54287 (17)	0.42502 (15)	0.25006 (9)	0.0246 (4)
C18	0.55335 (19)	0.47308 (18)	0.32980 (10)	0.0314 (5)
C19	0.5129 (2)	0.3808 (2)	0.38883 (10)	0.0366 (6)
C20	0.46166 (19)	0.24306 (19)	0.36642 (10)	0.0340 (5)
C21	0.45376 (18)	0.19449 (17)	0.28735 (10)	0.0313 (5)
C22	0.49622 (17)	0.28577 (15)	0.22782 (9)	0.0258 (4)
C23	0.36440 (17)	0.42562 (15)	0.06618 (8)	0.0234 (4)
C24	0.19359 (16)	0.54614 (14)	0.08942 (8)	0.0203 (4)
C25	0.32640 (15)	0.62082 (13)	0.14231 (8)	0.0181 (4)
C26	0.37432 (17)	0.76406 (14)	0.11053 (9)	0.0235 (4)
C27	0.29616 (15)	0.61719 (14)	0.23119 (8)	0.0188 (4)
C28	0.34294 (17)	0.73075 (15)	0.28478 (9)	0.0250 (4)
C29	0.32074 (18)	0.72166 (17)	0.36611 (10)	0.0312 (5)
C30	0.25095 (18)	0.59752 (18)	0.39255 (9)	0.0300 (5)
C31	0.19982 (18)	0.48331 (17)	0.34161 (9)	0.0280 (5)
C32	0.22340 (16)	0.49359 (15)	0.26027 (9)	0.0226 (4)
H2	1.09880	0.08820	0.32580	0.0390*
H2N	0.646 (2)	−0.124 (2)	0.0142 (12)	0.037 (5)*
H3	1.04140	−0.05190	0.43480	0.0490*
H5	0.92420	−0.38710	0.28060	0.0420*
H6	0.99110	−0.24960	0.17140	0.0330*
H10A	0.88320	0.24360	0.03680	0.0340*
H10B	0.95730	0.30860	0.12250	0.0340*
H10C	0.79550	0.31140	0.09860	0.0340*
H12	0.88430	0.32790	0.24650	0.0280*
H13	0.85700	0.32470	0.38590	0.0340*
H15	0.66860	−0.08150	0.36080	0.0320*
H16	0.69920	−0.07820	0.22210	0.0260*
H4N	0.170 (2)	0.3855 (19)	0.0117 (11)	0.031 (5)*
H18	0.58780	0.56820	0.34390	0.0380*
H19	0.52030	0.41170	0.44400	0.0440*
H21	0.41950	0.09920	0.27360	0.0370*
H22	0.49350	0.25380	0.17310	0.0310*
H26A	0.38990	0.75590	0.05310	0.0350*
H26B	0.46290	0.81250	0.14050	0.0350*
H26C	0.30080	0.81560	0.11770	0.0350*
H28	0.39080	0.81570	0.26540	0.0300*
H29	0.35290	0.79930	0.40270	0.0370*
H31	0.14980	0.39970	0.36150	0.0340*
H32	0.18970	0.41570	0.22400	0.0270*

	U11	U22	U33	U12	U13	U23
Cl1	0.0535 (3)	0.1057 (5)	0.0463 (3)	0.0147 (3)	0.0103 (2)	0.0444 (3)
S1	0.0190 (2)	0.0171 (2)	0.0295 (2)	0.0054 (1)	0.0028 (1)	0.0019 (1)
F1	0.0520 (7)	0.0584 (7)	0.0186 (4)	0.0092 (6)	0.0052 (4)	−0.0020 (4)
O1	0.0364 (7)	0.0210 (5)	0.0314 (6)	0.0107 (5)	0.0030 (5)	−0.0080 (4)
O2	0.0221 (6)	0.0302 (6)	0.0276 (5)	0.0082 (5)	−0.0011 (4)	−0.0042 (4)
O3	0.0229 (6)	0.0182 (5)	0.0510 (7)	0.0013 (4)	−0.0054 (5)	−0.0014 (5)
O4	0.0285 (6)	0.0317 (6)	0.0378 (6)	0.0155 (5)	0.0141 (5)	0.0092 (5)
N1	0.0203 (6)	0.0147 (5)	0.0224 (6)	0.0064 (5)	0.0025 (5)	−0.0006 (4)
N2	0.0227 (7)	0.0201 (6)	0.0204 (6)	0.0017 (5)	0.0021 (5)	−0.0065 (5)
C1	0.0226 (8)	0.0254 (8)	0.0254 (7)	0.0096 (6)	0.0004 (6)	0.0015 (6)
C2	0.0339 (9)	0.0370 (9)	0.0283 (8)	0.0156 (7)	−0.0056 (7)	−0.0050 (7)
C3	0.0420 (11)	0.0633 (13)	0.0245 (8)	0.0260 (10)	0.0002 (7)	0.0011 (8)
C4	0.0297 (9)	0.0606 (13)	0.0338 (9)	0.0160 (9)	0.0046 (7)	0.0213 (8)
C5	0.0292 (9)	0.0355 (9)	0.0400 (9)	0.0057 (7)	−0.0013 (7)	0.0139 (7)
C6	0.0277 (8)	0.0244 (8)	0.0290 (8)	0.0057 (6)	−0.0006 (6)	0.0042 (6)
C7	0.0283 (8)	0.0156 (6)	0.0192 (6)	0.0045 (6)	0.0047 (5)	−0.0015 (5)
C8	0.0220 (7)	0.0182 (6)	0.0164 (6)	0.0021 (5)	0.0027 (5)	0.0005 (5)
C9	0.0191 (7)	0.0127 (6)	0.0214 (6)	0.0048 (5)	0.0029 (5)	−0.0004 (5)
C10	0.0249 (8)	0.0166 (7)	0.0279 (7)	0.0057 (6)	0.0049 (6)	0.0057 (5)
C11	0.0185 (7)	0.0152 (6)	0.0200 (6)	0.0038 (5)	0.0013 (5)	−0.0012 (5)
C12	0.0232 (8)	0.0177 (7)	0.0263 (7)	0.0016 (6)	0.0030 (6)	−0.0031 (5)
C13	0.0297 (9)	0.0279 (8)	0.0269 (7)	0.0054 (7)	0.0000 (6)	−0.0102 (6)
C14	0.0285 (8)	0.0390 (9)	0.0179 (7)	0.0097 (7)	0.0028 (6)	−0.0012 (6)
C15	0.0287 (8)	0.0264 (8)	0.0242 (7)	0.0054 (6)	0.0041 (6)	0.0048 (6)
C16	0.0249 (8)	0.0180 (7)	0.0223 (7)	0.0029 (6)	0.0018 (6)	0.0005 (5)
Cl2	0.0499 (3)	0.0667 (4)	0.0426 (3)	0.0081 (3)	0.0044 (2)	0.0272 (2)
S2	0.0205 (2)	0.0163 (2)	0.0358 (2)	0.0056 (1)	0.0049 (2)	0.0018 (1)
F2	0.0560 (7)	0.0628 (7)	0.0196 (5)	0.0125 (6)	0.0054 (5)	0.0011 (4)
O5	0.0425 (7)	0.0245 (6)	0.0328 (6)	0.0144 (5)	0.0061 (5)	−0.0079 (4)
O6	0.0237 (6)	0.0278 (6)	0.0280 (5)	0.0056 (5)	0.0004 (4)	−0.0041 (4)
O7	0.0245 (6)	0.0162 (5)	0.0560 (8)	0.0032 (4)	−0.0033 (5)	−0.0025 (5)
O8	0.0296 (6)	0.0311 (6)	0.0500 (7)	0.0148 (5)	0.0166 (5)	0.0097 (5)
N3	0.0250 (7)	0.0154 (6)	0.0231 (6)	0.0069 (5)	0.0047 (5)	−0.0009 (4)
N4	0.0304 (7)	0.0214 (6)	0.0206 (6)	0.0045 (5)	0.0023 (5)	−0.0065 (5)
C17	0.0227 (8)	0.0210 (7)	0.0316 (8)	0.0090 (6)	−0.0001 (6)	0.0003 (6)
C18	0.0339 (9)	0.0307 (9)	0.0316 (8)	0.0146 (7)	−0.0055 (7)	−0.0052 (6)
C19	0.0395 (10)	0.0476 (11)	0.0269 (8)	0.0208 (8)	−0.0030 (7)	−0.0006 (7)
C20	0.0297 (9)	0.0434 (10)	0.0318 (8)	0.0131 (8)	0.0017 (7)	0.0126 (7)
C21	0.0288 (9)	0.0251 (8)	0.0383 (9)	0.0037 (7)	−0.0029 (7)	0.0061 (7)
C22	0.0290 (8)	0.0207 (7)	0.0277 (7)	0.0066 (6)	−0.0004 (6)	0.0007 (6)
C23	0.0304 (8)	0.0185 (7)	0.0218 (7)	0.0058 (6)	0.0054 (6)	−0.0002 (5)
C24	0.0253 (8)	0.0166 (6)	0.0183 (6)	0.0024 (6)	0.0042 (5)	0.0014 (5)
C25	0.0196 (7)	0.0128 (6)	0.0226 (6)	0.0045 (5)	0.0040 (5)	0.0005 (5)
C26	0.0241 (8)	0.0142 (6)	0.0326 (8)	0.0040 (6)	0.0053 (6)	0.0048 (5)
C27	0.0196 (7)	0.0157 (6)	0.0207 (6)	0.0037 (5)	0.0015 (5)	−0.0016 (5)
C28	0.0261 (8)	0.0176 (7)	0.0296 (7)	0.0022 (6)	0.0030 (6)	−0.0053 (5)
C29	0.0330 (9)	0.0314 (8)	0.0273 (8)	0.0061 (7)	−0.0001 (7)	−0.0116 (6)
C30	0.0314 (9)	0.0418 (10)	0.0180 (7)	0.0108 (7)	0.0026 (6)	−0.0008 (6)
C31	0.0297 (9)	0.0276 (8)	0.0259 (7)	0.0036 (7)	0.0035 (6)	0.0055 (6)
C32	0.0247 (8)	0.0181 (7)	0.0231 (7)	0.0017 (6)	0.0009 (6)	−0.0004 (5)

Cl1—C4	1.738 (2)	C14—C15	1.381 (2)
Cl2—C20	1.7390 (18)	C15—C16	1.387 (2)
S1—O4	1.4214 (12)	C2—H2	0.9500
S1—N1	1.6669 (13)	C3—H3	0.9500
S1—C1	1.7601 (16)	C5—H5	0.9500
S1—O3	1.4240 (12)	C6—H6	0.9500
S2—O7	1.4254 (12)	C10—H10A	0.9800
S2—O8	1.4186 (14)	C10—H10B	0.9800
S2—C17	1.7638 (15)	C10—H10C	0.9800
S2—N3	1.6605 (14)	C12—H12	0.9500
F1—C14	1.3556 (18)	C13—H13	0.9500
F2—C30	1.3546 (18)	C15—H15	0.9500
O1—C7	1.2026 (19)	C16—H16	0.9500
O2—C8	1.208 (2)	C17—C22	1.393 (2)
O5—C23	1.203 (2)	C17—C18	1.383 (2)
O6—C24	1.206 (2)	C18—C19	1.386 (2)
N1—C7	1.4018 (18)	C19—C20	1.384 (3)
N1—C9	1.4939 (19)	C20—C21	1.376 (2)
N2—C7	1.378 (2)	C21—C22	1.390 (2)
N2—C8	1.3666 (19)	C24—C25	1.537 (2)
N2—H2N	0.84 (2)	C25—C26	1.5281 (19)
N3—C23	1.4052 (18)	C25—C27	1.5249 (19)
N3—C25	1.4996 (19)	C27—C32	1.398 (2)
N4—C23	1.375 (2)	C27—C28	1.390 (2)
N4—C24	1.3681 (19)	C28—C29	1.386 (2)
N4—H4N	0.875 (19)	C29—C30	1.376 (2)
C1—C6	1.394 (2)	C30—C31	1.375 (2)
C1—C2	1.383 (2)	C31—C32	1.390 (2)
C2—C3	1.387 (2)	C18—H18	0.9500
C3—C4	1.385 (3)	C19—H19	0.9500
C4—C5	1.376 (3)	C21—H21	0.9500
C5—C6	1.388 (2)	C22—H22	0.9500
C8—C9	1.538 (2)	C26—H26A	0.9800
C9—C10	1.5250 (19)	C26—H26B	0.9800
C9—C11	1.5254 (19)	C26—H26C	0.9800
C11—C16	1.397 (2)	C28—H28	0.9500
C11—C12	1.391 (2)	C29—H29	0.9500
C12—C13	1.393 (2)	C31—H31	0.9500
C13—C14	1.375 (2)	C32—H32	0.9500
O3—S1—O4	120.54 (7)	H10B—C10—H10C	109.00
O3—S1—N1	105.32 (7)	C9—C10—H10A	109.00
O3—S1—C1	108.55 (8)	C9—C10—H10C	109.00
O4—S1—N1	107.44 (7)	H10A—C10—H10B	109.00
O4—S1—C1	109.31 (7)	C13—C12—H12	120.00
N1—S1—C1	104.49 (7)	C11—C12—H12	120.00
O8—S2—N3	107.85 (7)	C14—C13—H13	121.00
O8—S2—C17	109.35 (8)	C12—C13—H13	121.00
N3—S2—C17	104.29 (7)	C16—C15—H15	121.00
O7—S2—C17	108.38 (7)	C14—C15—H15	121.00
O7—S2—O8	120.43 (7)	C15—C16—H16	119.00
O7—S2—N3	105.34 (7)	C11—C16—H16	119.00
C7—N1—C9	111.78 (12)	S2—C17—C18	119.53 (12)
S1—N1—C9	124.37 (9)	C18—C17—C22	121.65 (14)
S1—N1—C7	122.81 (11)	S2—C17—C22	118.78 (11)
C7—N2—C8	113.69 (12)	C17—C18—C19	119.20 (16)
C8—N2—H2N	122.9 (14)	C18—C19—C20	119.16 (16)
C7—N2—H2N	123.1 (14)	Cl2—C20—C21	118.94 (14)
S2—N3—C25	124.18 (9)	Cl2—C20—C19	119.28 (13)
S2—N3—C23	123.49 (11)	C19—C20—C21	121.79 (16)
C23—N3—C25	111.33 (12)	C20—C21—C22	119.53 (15)
C23—N4—C24	114.09 (12)	C17—C22—C21	118.62 (14)
C24—N4—H4N	123.3 (13)	N3—C23—N4	106.55 (13)
C23—N4—H4N	122.6 (13)	O5—C23—N3	126.46 (15)
S1—C1—C6	118.72 (12)	O5—C23—N4	126.98 (14)
C2—C1—C6	121.81 (15)	O6—C24—N4	127.18 (14)
S1—C1—C2	119.40 (13)	O6—C24—C25	125.42 (13)
C1—C2—C3	119.02 (17)	N4—C24—C25	107.39 (13)
C2—C3—C4	118.98 (16)	N3—C25—C24	100.55 (10)
Cl1—C4—C3	119.61 (14)	C24—C25—C26	107.20 (11)
Cl1—C4—C5	118.26 (15)	C24—C25—C27	110.25 (12)
C3—C4—C5	122.13 (17)	C26—C25—C27	115.47 (11)
C4—C5—C6	119.27 (17)	N3—C25—C26	110.75 (12)
C1—C6—C5	118.64 (15)	N3—C25—C27	111.50 (11)
O1—C7—N1	126.44 (15)	C28—C27—C32	118.95 (13)
N1—C7—N2	106.47 (12)	C25—C27—C28	122.38 (12)
O1—C7—N2	127.08 (14)	C25—C27—C32	118.63 (12)
N2—C8—C9	107.77 (13)	C27—C28—C29	120.87 (14)
O2—C8—C9	125.18 (13)	C28—C29—C30	118.37 (15)
O2—C8—N2	127.05 (14)	F2—C30—C31	118.41 (15)
C10—C9—C11	115.85 (11)	F2—C30—C29	118.72 (15)
N1—C9—C8	100.25 (10)	C29—C30—C31	122.88 (15)
N1—C9—C10	111.26 (12)	C30—C31—C32	118.17 (15)
C8—C9—C10	107.59 (11)	C27—C32—C31	120.74 (14)
C8—C9—C11	109.55 (12)	C17—C18—H18	120.00
N1—C9—C11	111.12 (11)	C19—C18—H18	120.00
C12—C11—C16	118.98 (13)	C18—C19—H19	120.00
C9—C11—C16	118.47 (12)	C20—C19—H19	120.00
C9—C11—C12	122.52 (12)	C20—C21—H21	120.00
C11—C12—C13	120.71 (14)	C22—C21—H21	120.00
C12—C13—C14	118.31 (14)	C17—C22—H22	121.00
F1—C14—C15	118.21 (15)	C21—C22—H22	121.00
C13—C14—C15	122.95 (14)	C25—C26—H26A	109.00
F1—C14—C13	118.84 (15)	C25—C26—H26B	109.00
C14—C15—C16	117.94 (14)	C25—C26—H26C	109.00
C11—C16—C15	121.08 (13)	H26A—C26—H26B	110.00
C3—C2—H2	120.00	H26A—C26—H26C	109.00
C1—C2—H2	121.00	H26B—C26—H26C	109.00
C2—C3—H3	120.00	C27—C28—H28	120.00
C4—C3—H3	121.00	C29—C28—H28	120.00
C4—C5—H5	120.00	C28—C29—H29	121.00
C6—C5—H5	120.00	C30—C29—H29	121.00
C1—C6—H6	121.00	C30—C31—H31	121.00
C5—C6—H6	121.00	C32—C31—H31	121.00
C9—C10—H10B	109.00	C27—C32—H32	120.00
H10A—C10—H10C	109.00	C31—C32—H32	120.00
O3—S1—N1—C7	169.06 (11)	C2—C3—C4—C5	3.6 (3)
O3—S1—N1—C9	−23.58 (13)	Cl1—C4—C5—C6	177.33 (14)
O4—S1—N1—C7	39.41 (13)	C3—C4—C5—C6	−2.1 (3)
O4—S1—N1—C9	−153.24 (11)	C4—C5—C6—C1	−1.6 (3)
C1—S1—N1—C7	−76.64 (12)	O2—C8—C9—C11	63.69 (17)
C1—S1—N1—C9	90.72 (12)	O2—C8—C9—C10	−63.03 (18)
O3—S1—C1—C2	2.56 (16)	N2—C8—C9—C11	−116.37 (12)
O3—S1—C1—C6	179.52 (13)	N2—C8—C9—N1	0.56 (13)
O4—S1—C1—C2	135.82 (14)	N2—C8—C9—C10	116.91 (12)
O4—S1—C1—C6	−47.21 (15)	O2—C8—C9—N1	−179.38 (13)
N1—S1—C1—C2	−109.44 (14)	C8—C9—C11—C12	−133.46 (14)
N1—S1—C1—C6	67.53 (14)	C8—C9—C11—C16	48.46 (17)
O7—S2—N3—C23	168.37 (12)	C10—C9—C11—C12	−11.6 (2)
O7—S2—N3—C25	−24.06 (13)	C10—C9—C11—C16	170.35 (14)
O8—S2—N3—C23	38.58 (13)	N1—C9—C11—C12	116.69 (15)
O8—S2—N3—C25	−153.85 (11)	N1—C9—C11—C16	−61.39 (17)
C17—S2—N3—C23	−77.60 (13)	C9—C11—C12—C13	−176.64 (15)
C17—S2—N3—C25	89.98 (12)	C12—C11—C16—C15	−0.9 (2)
O7—S2—C17—C18	−0.26 (17)	C16—C11—C12—C13	1.4 (2)
O7—S2—C17—C22	177.31 (13)	C9—C11—C16—C15	177.24 (14)
O8—S2—C17—C18	132.76 (15)	C11—C12—C13—C14	−0.5 (2)
O8—S2—C17—C22	−49.67 (16)	C12—C13—C14—C15	−1.1 (3)
N3—S2—C17—C18	−112.11 (15)	C12—C13—C14—F1	178.57 (15)
N3—S2—C17—C22	65.46 (15)	C13—C14—C15—C16	1.6 (3)
S1—N1—C9—C8	−170.14 (9)	F1—C14—C15—C16	−178.08 (15)
S1—N1—C9—C10	76.29 (14)	C14—C15—C16—C11	−0.6 (2)
S1—N1—C9—C11	−54.40 (15)	S2—C17—C18—C19	175.79 (15)
S1—N1—C7—O1	−8.4 (2)	C22—C17—C18—C19	−1.7 (3)
S1—N1—C7—N2	170.79 (9)	S2—C17—C22—C21	−174.77 (13)
C9—N1—C7—O1	−177.21 (14)	C18—C17—C22—C21	2.8 (3)
C9—N1—C7—N2	2.00 (15)	C17—C18—C19—C20	−0.7 (3)
C7—N1—C9—C8	−1.56 (14)	C18—C19—C20—Cl2	−177.81 (15)
C7—N1—C9—C10	−115.13 (13)	C18—C19—C20—C21	2.0 (3)
C7—N1—C9—C11	114.18 (13)	Cl2—C20—C21—C22	178.86 (14)
C7—N2—C8—O2	−179.43 (14)	C19—C20—C21—C22	−1.0 (3)
C7—N2—C8—C9	0.64 (16)	C20—C21—C22—C17	−1.4 (3)
C8—N2—C7—O1	177.57 (14)	O6—C24—C25—N3	178.72 (13)
C8—N2—C7—N1	−1.63 (16)	O6—C24—C25—C26	−65.50 (18)
C25—N3—C23—O5	−178.52 (14)	O6—C24—C25—C27	60.94 (18)
S2—N3—C23—O5	−9.5 (2)	N4—C24—C25—N3	−2.26 (13)
S2—N3—C23—N4	169.79 (10)	N4—C24—C25—C26	113.52 (13)
C23—N3—C25—C27	117.74 (12)	N4—C24—C25—C27	−120.04 (12)
C25—N3—C23—N4	0.80 (15)	N3—C25—C27—C28	111.40 (15)
S2—N3—C25—C24	−168.02 (9)	N3—C25—C27—C32	−66.12 (17)
S2—N3—C25—C26	78.89 (14)	C24—C25—C27—C28	−137.80 (14)
S2—N3—C25—C27	−51.16 (15)	C24—C25—C27—C32	44.67 (18)
C23—N3—C25—C24	0.88 (14)	C26—C25—C27—C28	−16.1 (2)
C23—N3—C25—C26	−112.22 (13)	C26—C25—C27—C32	166.34 (14)
C23—N4—C24—O6	−177.93 (14)	C25—C27—C28—C29	−176.22 (15)
C24—N4—C23—O5	176.83 (14)	C32—C27—C28—C29	1.3 (2)
C24—N4—C23—N3	−2.48 (16)	C25—C27—C32—C31	176.65 (15)
C23—N4—C24—C25	3.07 (16)	C28—C27—C32—C31	−1.0 (2)
S1—C1—C2—C3	174.66 (14)	C27—C28—C29—C30	−0.1 (3)
C2—C1—C6—C5	3.8 (3)	C28—C29—C30—F2	178.10 (16)
C6—C1—C2—C3	−2.2 (3)	C28—C29—C30—C31	−1.4 (3)
S1—C1—C6—C5	−173.13 (13)	F2—C30—C31—C32	−177.78 (15)
C1—C2—C3—C4	−1.5 (3)	C29—C30—C31—C32	1.8 (3)
C2—C3—C4—Cl1	−175.76 (15)	C30—C31—C32—C27	−0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O5i	0.84 (2)	2.23 (2)	2.9383 (17)	143.0 (18)
N4—H4N···O1i	0.875 (19)	2.103 (19)	2.8595 (17)	144.4 (17)
C6—H6···O6ii	0.95	2.53	3.339 (2)	143
C16—H16···O7iii	0.95	2.38	3.2330 (18)	149
C26—H26C···O4iv	0.98	2.41	3.358 (2)	162
C32—H32···O3v	0.95	2.38	3.2715 (19)	155
C3—H3···F1vi	0.95	2.76	3.308 (2)	118
C29—H29···F1vii	0.95	2.66	3.3715 (19)	133
C13—H13···F2vii	0.95	2.75	3.4627 (19)	133
C19—H19···F2vii	0.95	2.69	3.223 (2)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O5i	0.84 (2)	2.23 (2)	2.9383 (17)	143.0 (18)
N4—H4N⋯O1i	0.875 (19)	2.103 (19)	2.8595 (17)	144.4 (17)
C6—H6⋯O6ii	0.95	2.53	3.339 (2)	143
C16—H16⋯O7iii	0.95	2.38	3.2330 (18)	149
C26—H26C⋯O4iv	0.98	2.41	3.358 (2)	162
C32—H32⋯O3v	0.95	2.38	3.2715 (19)	155
C3—H3⋯F1vi	0.95	2.76	3.308 (2)	118
C29—H29⋯F1vii	0.95	2.66	3.3715 (19)	133
C13—H13⋯F2vii	0.95	2.75	3.4627 (19)	133
C19—H19⋯F2vii	0.95	2.69	3.223 (2)	116

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