2-(4-Chloro-phen-yl)-5-(cyclo-hex-1-en-1-yl)-3-(4-methyl-phenyl-sulfon-yl)-1-phenyl-imidazolidin-4-one.

In the title compound, C(28)H(27)ClN(2)O(3)S, the central imidazolidine ring adopts an envelope conformation with the C atom bearing the chloro-phenyl ring at the flap. The geometry around the S atom is distorted tetra-hedral. Three methyl-ene groups of the cyclo-hexene ring are disordered over two sets of sites [site occupancies = 0.562 (10) and 0.438 (10)]. The crystal packing is stabilized by C-H⋯π inter-actions.

Related literature

For the biological activity of sulfonamides, see: Zareef et al. (2007 ▶); Chohan & Shad (2008 ▶); Pomarnacka & Kozlarska-Kedra (2003 ▶); Nieto et al. (2005 ▶); Wang et al. (1995 ▶). For a related structure, see: Ranjith et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For ring asymmetry parameters, see: Nardelli et al. (1983 ▶).

Experimental

Crystal data

C28H27ClN2O3S

M = 507.03

Monoclinic,

a = 10.9974 (3) Å

b = 13.4095 (4) Å

c = 17.4434 (5) Å

β = 105.103 (2)°

V = 2483.52 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.934, T max = 0.950

32488 measured reflections

7366 independent reflections

4844 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.139

S = 1.01

7366 reflections

346 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028133/bt5573sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028133/bt5573Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028133/bt5573Isup3.cml

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

C28H27ClN2O3S	F(000) = 1064
Mr = 507.03	Dx = 1.356 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7366 reflections
a = 10.9974 (3) Å	θ = 2.0–30.4°
b = 13.4095 (4) Å	µ = 0.27 mm−1
c = 17.4434 (5) Å	T = 293 K
β = 105.103 (2)°	Block, white crystalline
V = 2483.52 (12) Å3	0.25 × 0.22 × 0.19 mm
Z = 4

Bruker APEXII CCD area detector diffractometer	7366 independent reflections
Radiation source: fine-focus sealed tube	4844 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω and φ scans	θmax = 30.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.934, Tmax = 0.950	k = −18→17
32488 measured reflections	l = −24→24

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.0638P)2 + 0.6285P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
7366 reflections	Δρmax = 0.30 e Å−3
346 parameters	Δρmin = −0.33 e Å−3
4 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: 0.0016 (5)

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	Occ. (<1)
C1	0.3220 (3)	0.3780 (3)	−0.10334 (16)	0.0984 (11)
H1A	0.2431	0.3432	−0.1139	0.148*
H1B	0.3896	0.3306	−0.0959	0.148*
H1C	0.3229	0.4206	−0.1474	0.148*
C2	0.3385 (2)	0.4401 (2)	−0.02909 (13)	0.0630 (6)
C3	0.3809 (2)	0.39928 (18)	0.04443 (15)	0.0657 (6)
H3	0.4018	0.3319	0.0488	0.079*
C4	0.3938 (2)	0.45477 (15)	0.11277 (12)	0.0534 (5)
H4	0.4217	0.4250	0.1624	0.064*
C5	0.36483 (15)	0.55480 (14)	0.10642 (10)	0.0399 (4)
C6	0.32259 (19)	0.59833 (18)	0.03261 (11)	0.0551 (5)
H6	0.3030	0.6659	0.0279	0.066*
C7	0.3098 (2)	0.5397 (2)	−0.03421 (12)	0.0683 (7)
H7	0.2809	0.5687	−0.0841	0.082*
C8	0.15703 (15)	0.68904 (13)	0.20985 (9)	0.0357 (3)
H8	0.1924	0.7545	0.2284	0.043*
C9	0.08827 (14)	0.69380 (12)	0.12235 (9)	0.0335 (3)
C10	0.01018 (16)	0.61671 (13)	0.08682 (10)	0.0393 (4)
H10	−0.0062	0.5645	0.1178	0.047*
C11	−0.04370 (16)	0.61627 (14)	0.00593 (10)	0.0428 (4)
H11	−0.0969	0.5646	−0.0176	0.051*
C12	−0.01773 (16)	0.69310 (14)	−0.03927 (9)	0.0420 (4)
C13	0.05538 (18)	0.77282 (14)	−0.00504 (10)	0.0467 (4)
H13	0.0696	0.8257	−0.0361	0.056*
C14	0.10737 (17)	0.77306 (13)	0.07623 (10)	0.0412 (4)
H14	0.1557	0.8271	0.1001	0.049*
C15	−0.02845 (16)	0.69953 (14)	0.26500 (9)	0.0392 (4)
C16	−0.05654 (17)	0.79523 (14)	0.23440 (10)	0.0450 (4)
H16	−0.0010	0.8280	0.2109	0.054*
C17	−0.1665 (2)	0.84149 (17)	0.23890 (12)	0.0558 (5)
H17	−0.1839	0.9057	0.2188	0.067*
C18	−0.2509 (2)	0.79421 (19)	0.27261 (12)	0.0606 (6)
H18	−0.3255	0.8255	0.2744	0.073*
C19	−0.22360 (19)	0.70099 (19)	0.30332 (12)	0.0585 (5)
H19	−0.2799	0.6691	0.3267	0.070*
C20	−0.11374 (18)	0.65312 (16)	0.30031 (11)	0.0498 (4)
H20	−0.0965	0.5897	0.3219	0.060*
C21	0.11459 (17)	0.55093 (13)	0.29037 (9)	0.0407 (4)
H21	0.0469	0.5047	0.2652	0.049*
C22	0.23143 (17)	0.52896 (14)	0.26277 (9)	0.0416 (4)
C23	0.14710 (17)	0.53918 (13)	0.37990 (9)	0.0401 (4)
N1	0.25822 (13)	0.61314 (11)	0.22405 (8)	0.0383 (3)
N2	0.08217 (14)	0.65180 (11)	0.26115 (8)	0.0416 (3)
O1	0.48872 (12)	0.58412 (12)	0.25198 (8)	0.0570 (4)
O2	0.38986 (13)	0.72903 (10)	0.17229 (9)	0.0552 (3)
O3	0.29106 (14)	0.45255 (10)	0.27358 (8)	0.0552 (3)
S1	0.38901 (4)	0.62668 (4)	0.19262 (2)	0.04154 (13)
Cl1	−0.07606 (6)	0.68766 (5)	−0.14158 (3)	0.06699 (18)
C24	0.1128 (2)	0.45825 (15)	0.41165 (11)	0.0495 (4)
H24	0.0584	0.4123	0.3803	0.059*
C28	0.2297 (2)	0.61722 (17)	0.42755 (11)	0.0626 (6)
H28A	0.1981	0.6823	0.4074	0.075*
H28B	0.3137	0.6102	0.4202	0.075*
C25	0.1632 (15)	0.4414 (10)	0.4994 (2)	0.062 (3)	0.562 (10)
H25A	0.1889	0.3723	0.5081	0.074*	0.562 (10)
H25B	0.0956	0.4525	0.5247	0.074*	0.562 (10)
C26	0.2734 (7)	0.5069 (4)	0.5394 (3)	0.070 (2)	0.562 (10)
H26A	0.2921	0.4992	0.5966	0.083*	0.562 (10)
H26B	0.3475	0.4881	0.5225	0.083*	0.562 (10)
C27	0.2384 (8)	0.6130 (3)	0.5167 (2)	0.0693 (18)	0.562 (10)
H27A	0.3023	0.6585	0.5460	0.083*	0.562 (10)
H27B	0.1582	0.6300	0.5268	0.083*	0.562 (10)
C25'	0.1412 (18)	0.4256 (11)	0.4969 (3)	0.052 (2)	0.438 (10)
H25C	0.1931	0.3661	0.5050	0.062*	0.438 (10)
H25D	0.0637	0.4109	0.5113	0.062*	0.438 (10)
C26'	0.2104 (10)	0.5104 (8)	0.5469 (5)	0.075 (3)	0.438 (10)
H26C	0.1488	0.5540	0.5605	0.090*	0.438 (10)
H26D	0.2621	0.4829	0.5961	0.090*	0.438 (10)
C27'	0.2928 (6)	0.5719 (8)	0.5090 (3)	0.092 (4)	0.438 (10)
H27C	0.3623	0.5306	0.5035	0.111*	0.438 (10)
H27D	0.3281	0.6259	0.5450	0.111*	0.438 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0785 (18)	0.152 (3)	0.0741 (17)	−0.0432 (18)	0.0375 (14)	−0.0598 (18)
C2	0.0472 (11)	0.0952 (18)	0.0520 (12)	−0.0222 (12)	0.0228 (9)	−0.0241 (12)
C3	0.0725 (15)	0.0610 (13)	0.0723 (15)	−0.0144 (11)	0.0345 (12)	−0.0184 (11)
C4	0.0604 (12)	0.0556 (12)	0.0468 (10)	−0.0013 (10)	0.0186 (9)	0.0022 (9)
C5	0.0349 (8)	0.0528 (10)	0.0340 (8)	−0.0017 (7)	0.0124 (6)	0.0003 (7)
C6	0.0549 (11)	0.0706 (14)	0.0416 (10)	0.0078 (10)	0.0159 (8)	0.0099 (9)
C7	0.0568 (12)	0.117 (2)	0.0324 (9)	−0.0009 (13)	0.0133 (9)	0.0025 (11)
C8	0.0349 (8)	0.0439 (9)	0.0279 (7)	−0.0005 (7)	0.0077 (6)	−0.0007 (6)
C9	0.0319 (7)	0.0399 (9)	0.0290 (7)	0.0002 (6)	0.0082 (6)	0.0011 (6)
C10	0.0420 (9)	0.0409 (9)	0.0345 (8)	−0.0053 (7)	0.0091 (7)	0.0022 (7)
C11	0.0399 (9)	0.0457 (10)	0.0391 (9)	−0.0019 (7)	0.0037 (7)	−0.0053 (7)
C12	0.0423 (9)	0.0531 (10)	0.0276 (7)	0.0079 (8)	0.0039 (6)	0.0011 (7)
C13	0.0529 (10)	0.0473 (10)	0.0382 (9)	−0.0002 (8)	0.0085 (8)	0.0112 (7)
C14	0.0435 (9)	0.0398 (9)	0.0382 (8)	−0.0059 (7)	0.0068 (7)	0.0023 (7)
C15	0.0369 (8)	0.0552 (10)	0.0246 (7)	0.0012 (7)	0.0062 (6)	−0.0038 (7)
C16	0.0458 (10)	0.0537 (11)	0.0356 (8)	0.0012 (8)	0.0108 (7)	−0.0030 (7)
C17	0.0557 (12)	0.0637 (13)	0.0466 (10)	0.0147 (10)	0.0110 (9)	−0.0020 (9)
C18	0.0450 (11)	0.0851 (16)	0.0516 (11)	0.0149 (11)	0.0121 (9)	−0.0055 (11)
C19	0.0423 (10)	0.0897 (17)	0.0468 (10)	−0.0004 (10)	0.0174 (8)	0.0024 (10)
C20	0.0451 (10)	0.0666 (12)	0.0390 (9)	0.0030 (9)	0.0134 (8)	0.0060 (8)
C21	0.0455 (9)	0.0469 (10)	0.0306 (8)	−0.0008 (8)	0.0114 (7)	0.0013 (7)
C22	0.0468 (10)	0.0495 (10)	0.0284 (7)	0.0019 (8)	0.0095 (7)	0.0012 (7)
C23	0.0478 (9)	0.0443 (9)	0.0297 (7)	0.0018 (8)	0.0128 (7)	0.0017 (7)
N1	0.0366 (7)	0.0478 (8)	0.0314 (6)	0.0043 (6)	0.0103 (5)	0.0039 (6)
N2	0.0430 (8)	0.0506 (8)	0.0350 (7)	0.0067 (7)	0.0169 (6)	0.0086 (6)
O1	0.0382 (7)	0.0846 (10)	0.0426 (7)	0.0081 (7)	0.0006 (5)	−0.0051 (7)
O2	0.0499 (8)	0.0530 (8)	0.0662 (9)	−0.0085 (6)	0.0217 (7)	−0.0033 (7)
O3	0.0656 (9)	0.0516 (8)	0.0523 (8)	0.0137 (7)	0.0225 (7)	0.0076 (6)
S1	0.0334 (2)	0.0542 (3)	0.0366 (2)	−0.00127 (18)	0.00827 (16)	−0.00333 (18)
Cl1	0.0809 (4)	0.0804 (4)	0.0305 (2)	0.0147 (3)	−0.0021 (2)	0.0009 (2)
C24	0.0613 (11)	0.0503 (11)	0.0409 (9)	0.0044 (9)	0.0207 (8)	0.0039 (8)
C28	0.0794 (15)	0.0635 (14)	0.0400 (10)	−0.0123 (11)	0.0065 (10)	−0.0029 (9)
C25	0.093 (8)	0.054 (4)	0.045 (3)	−0.002 (3)	0.030 (3)	0.012 (3)
C26	0.094 (5)	0.076 (3)	0.033 (2)	0.006 (4)	0.006 (3)	0.004 (2)
C27	0.106 (5)	0.064 (3)	0.037 (2)	0.004 (3)	0.016 (2)	−0.0115 (18)
C25'	0.064 (5)	0.052 (5)	0.044 (4)	0.006 (3)	0.024 (3)	0.021 (3)
C26'	0.099 (7)	0.090 (5)	0.042 (3)	−0.016 (5)	0.029 (4)	0.010 (3)
C27'	0.101 (6)	0.137 (10)	0.036 (3)	−0.068 (6)	0.013 (3)	−0.004 (4)

C1—C2	1.511 (3)	C18—H18	0.9300
C1—H1A	0.9600	C19—C20	1.381 (3)
C1—H1B	0.9600	C19—H19	0.9300
C1—H1C	0.9600	C20—H20	0.9300
C2—C3	1.360 (3)	C21—N2	1.457 (2)
C2—C7	1.370 (4)	C21—C22	1.514 (2)
C3—C4	1.381 (3)	C21—C23	1.517 (2)
C3—H3	0.9300	C21—H21	0.9800
C4—C5	1.376 (3)	C22—O3	1.204 (2)
C4—H4	0.9300	C22—N1	1.386 (2)
C5—C6	1.379 (2)	C23—C24	1.317 (3)
C5—S1	1.7471 (17)	C23—C28	1.489 (3)
C6—C7	1.382 (3)	N1—S1	1.6774 (14)
C6—H6	0.9300	O1—S1	1.4173 (13)
C7—H7	0.9300	O2—S1	1.4181 (15)
C8—N2	1.453 (2)	C24—C25	1.502 (3)
C8—N1	1.480 (2)	C24—C25'	1.502 (3)
C8—C9	1.518 (2)	C24—H24	0.9300
C8—H8	0.9800	C28—C27	1.534 (3)
C9—C14	1.382 (2)	C28—C27'	1.535 (4)
C9—C10	1.383 (2)	C28—H28A	0.9700
C10—C11	1.381 (2)	C28—H28B	0.9700
C10—H10	0.9300	C25—C26	1.511 (6)
C11—C12	1.372 (3)	C25—H25A	0.9700
C11—H11	0.9300	C25—H25B	0.9700
C12—C13	1.377 (3)	C26—C27	1.501 (5)
C12—Cl1	1.7335 (16)	C26—H26A	0.9700
C13—C14	1.384 (2)	C26—H26B	0.9700
C13—H13	0.9300	C27—H27A	0.9700
C14—H14	0.9300	C27—H27B	0.9700
C15—N2	1.392 (2)	C25'—C26'	1.511 (6)
C15—C16	1.393 (3)	C25'—H25C	0.9700
C15—C20	1.395 (3)	C25'—H25D	0.9700
C16—C17	1.380 (3)	C26'—C27'	1.501 (5)
C16—H16	0.9300	C26'—H26C	0.9700
C17—C18	1.375 (3)	C26'—H26D	0.9700
C17—H17	0.9300	C27'—H27C	0.9700
C18—C19	1.362 (3)	C27'—H27D	0.9700
C2—C1—H1A	109.5	C22—C21—H21	110.1
C2—C1—H1B	109.5	C23—C21—H21	110.1
H1A—C1—H1B	109.5	O3—C22—N1	126.36 (16)
C2—C1—H1C	109.5	O3—C22—C21	126.04 (16)
H1A—C1—H1C	109.5	N1—C22—C21	107.59 (15)
H1B—C1—H1C	109.5	C24—C23—C28	122.96 (16)
C3—C2—C7	118.08 (19)	C24—C23—C21	120.13 (17)
C3—C2—C1	121.4 (3)	C28—C23—C21	116.58 (15)
C7—C2—C1	120.5 (2)	C22—N1—C8	113.30 (13)
C2—C3—C4	122.0 (2)	C22—N1—S1	123.83 (12)
C2—C3—H3	119.0	C8—N1—S1	122.82 (11)
C4—C3—H3	119.0	C15—N2—C8	120.95 (14)
C5—C4—C3	119.1 (2)	C15—N2—C21	123.20 (14)
C5—C4—H4	120.5	C8—N2—C21	114.10 (13)
C3—C4—H4	120.5	O1—S1—O2	121.21 (9)
C4—C5—C6	120.15 (18)	O1—S1—N1	106.48 (8)
C4—C5—S1	119.22 (14)	O2—S1—N1	104.40 (8)
C6—C5—S1	120.56 (15)	O1—S1—C5	108.78 (9)
C5—C6—C7	118.8 (2)	O2—S1—C5	109.16 (9)
C5—C6—H6	120.6	N1—S1—C5	105.69 (7)
C7—C6—H6	120.6	C23—C24—C25	118.8 (4)
C2—C7—C6	121.9 (2)	C23—C24—C25'	130.3 (4)
C2—C7—H7	119.1	C23—C24—H24	120.6
C6—C7—H7	119.1	C25—C24—H24	120.6
N2—C8—N1	100.51 (12)	C25'—C24—H24	108.9
N2—C8—C9	114.83 (13)	C23—C28—C27	114.1 (3)
N1—C8—C9	110.67 (13)	C23—C28—C27'	107.5 (4)
N2—C8—H8	110.2	C23—C28—H28A	108.7
N1—C8—H8	110.2	C27—C28—H28A	108.7
C9—C8—H8	110.2	C27'—C28—H28A	136.3
C14—C9—C10	119.00 (14)	C23—C28—H28B	108.7
C14—C9—C8	120.42 (14)	C27—C28—H28B	108.7
C10—C9—C8	120.51 (14)	C27'—C28—H28B	82.4
C11—C10—C9	120.81 (16)	H28A—C28—H28B	107.6
C11—C10—H10	119.6	C24—C25—C26	115.0 (5)
C9—C10—H10	119.6	C24—C25—H25A	108.5
C12—C11—C10	119.08 (16)	C26—C25—H25A	108.5
C12—C11—H11	120.5	C24—C25—H25B	108.5
C10—C11—H11	120.5	C26—C25—H25B	108.5
C11—C12—C13	121.28 (15)	H25A—C25—H25B	107.5
C11—C12—Cl1	118.91 (14)	C27—C26—C25	108.0 (8)
C13—C12—Cl1	119.79 (14)	C27—C26—H26A	110.1
C12—C13—C14	119.01 (16)	C25—C26—H26A	110.1
C12—C13—H13	120.5	C27—C26—H26B	110.1
C14—C13—H13	120.5	C25—C26—H26B	110.1
C9—C14—C13	120.66 (16)	H26A—C26—H26B	108.4
C9—C14—H14	119.7	C26—C27—C28	104.3 (3)
C13—C14—H14	119.7	C26—C27—H27A	110.9
N2—C15—C16	120.96 (16)	C28—C27—H27A	110.9
N2—C15—C20	120.84 (17)	C26—C27—H27B	110.9
C16—C15—C20	118.19 (17)	C28—C27—H27B	110.9
C17—C16—C15	120.16 (18)	H27A—C27—H27B	108.9
C17—C16—H16	119.9	C24—C25'—C26'	107.2 (6)
C15—C16—H16	119.9	C24—C25'—H25C	110.3
C18—C17—C16	121.0 (2)	C26'—C25'—H25C	110.3
C18—C17—H17	119.5	C24—C25'—H25D	110.3
C16—C17—H17	119.5	C26'—C25'—H25D	110.3
C19—C18—C17	119.2 (2)	H25C—C25'—H25D	108.5
C19—C18—H18	120.4	C27'—C26'—C25'	115.5 (9)
C17—C18—H18	120.4	C27'—C26'—H26C	108.4
C18—C19—C20	121.1 (2)	C25'—C26'—H26C	108.4
C18—C19—H19	119.5	C27'—C26'—H26D	108.4
C20—C19—H19	119.5	C25'—C26'—H26D	108.4
C19—C20—C15	120.3 (2)	H26C—C26'—H26D	107.5
C19—C20—H20	119.8	C26'—C27'—C28	116.5 (6)
C15—C20—H20	119.8	C26'—C27'—H27C	108.2
N2—C21—C22	102.71 (13)	C28—C27'—H27C	108.2
N2—C21—C23	115.29 (14)	C26'—C27'—H27D	108.2
C22—C21—C23	108.38 (14)	C28—C27'—H27D	108.2
N2—C21—H21	110.1	H27C—C27'—H27D	107.3
C7—C2—C3—C4	0.8 (3)	N2—C8—N1—S1	−169.07 (11)
C1—C2—C3—C4	−178.6 (2)	C9—C8—N1—S1	69.17 (16)
C2—C3—C4—C5	−1.0 (3)	C16—C15—N2—C8	−14.4 (2)
C3—C4—C5—C6	0.5 (3)	C20—C15—N2—C8	166.21 (16)
C3—C4—C5—S1	−176.61 (16)	C16—C15—N2—C21	−178.39 (15)
C4—C5—C6—C7	0.2 (3)	C20—C15—N2—C21	2.2 (2)
S1—C5—C6—C7	177.24 (16)	N1—C8—N2—C15	−177.89 (14)
C3—C2—C7—C6	−0.1 (3)	C9—C8—N2—C15	−59.1 (2)
C1—C2—C7—C6	179.3 (2)	N1—C8—N2—C21	−12.53 (17)
C5—C6—C7—C2	−0.4 (3)	C9—C8—N2—C21	106.25 (16)
N2—C8—C9—C14	140.82 (16)	C22—C21—N2—C15	172.55 (14)
N1—C8—C9—C14	−106.26 (18)	C23—C21—N2—C15	−69.8 (2)
N2—C8—C9—C10	−42.2 (2)	C22—C21—N2—C8	7.56 (18)
N1—C8—C9—C10	70.73 (19)	C23—C21—N2—C8	125.21 (15)
C14—C9—C10—C11	2.9 (3)	C22—N1—S1—O1	−38.92 (15)
C8—C9—C10—C11	−174.14 (16)	C8—N1—S1—O1	143.77 (13)
C9—C10—C11—C12	0.7 (3)	C22—N1—S1—O2	−168.25 (14)
C10—C11—C12—C13	−3.4 (3)	C8—N1—S1—O2	14.44 (14)
C10—C11—C12—Cl1	175.27 (14)	C22—N1—S1—C5	76.66 (15)
C11—C12—C13—C14	2.5 (3)	C8—N1—S1—C5	−100.65 (13)
Cl1—C12—C13—C14	−176.16 (15)	C4—C5—S1—O1	28.34 (18)
C10—C9—C14—C13	−3.8 (3)	C6—C5—S1—O1	−148.76 (15)
C8—C9—C14—C13	173.23 (16)	C4—C5—S1—O2	162.56 (15)
C12—C13—C14—C9	1.1 (3)	C6—C5—S1—O2	−14.54 (17)
N2—C15—C16—C17	−179.85 (16)	C4—C5—S1—N1	−85.66 (16)
C20—C15—C16—C17	−0.4 (2)	C6—C5—S1—N1	97.24 (16)
C15—C16—C17—C18	−0.7 (3)	C28—C23—C24—C25	−2.5 (9)
C16—C17—C18—C19	1.3 (3)	C21—C23—C24—C25	170.6 (9)
C17—C18—C19—C20	−0.7 (3)	C28—C23—C24—C25'	1.8 (12)
C18—C19—C20—C15	−0.4 (3)	C21—C23—C24—C25'	174.9 (12)
N2—C15—C20—C19	−179.59 (17)	C24—C23—C28—C27	−17.9 (4)
C16—C15—C20—C19	1.0 (3)	C21—C23—C28—C27	168.7 (3)
N2—C21—C22—O3	−179.64 (17)	C24—C23—C28—C27'	15.9 (5)
C23—C21—C22—O3	57.9 (2)	C21—C23—C28—C27'	−157.5 (4)
N2—C21—C22—N1	1.29 (17)	C23—C24—C25—C26	−14.2 (17)
C23—C21—C22—N1	−121.16 (15)	C25'—C24—C25—C26	−178 (9)
N2—C21—C23—C24	143.30 (18)	C24—C25—C26—C27	50.9 (15)
C22—C21—C23—C24	−102.3 (2)	C25—C26—C27—C28	−67.4 (9)
N2—C21—C23—C28	−43.1 (2)	C23—C28—C27—C26	52.2 (7)
C22—C21—C23—C28	71.3 (2)	C27'—C28—C27—C26	−32.6 (5)
O3—C22—N1—C8	171.37 (16)	C23—C24—C25'—C26'	6(2)
C21—C22—N1—C8	−9.56 (18)	C25—C24—C25'—C26'	24 (7)
O3—C22—N1—S1	−6.2 (3)	C24—C25'—C26'—C27'	−32.2 (19)
C21—C22—N1—S1	172.90 (11)	C25'—C26'—C27'—C28	54.7 (17)
N2—C8—N1—C22	13.37 (17)	C23—C28—C27'—C26'	−42.8 (12)
C9—C8—N1—C22	−108.40 (15)	C27—C28—C27'—C26'	64.7 (9)

Cg2 and Cg4 are the centroids of the C2–C7 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cg4i	0.96	2.91	3.490 (3)	120
C11—H11···Cg2i	0.93	2.86	3.612 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C2–C7 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cg4i	0.96	2.91	3.490 (3)	120
C11—H11⋯Cg2i	0.93	2.86	3.612 (2)	139

Symmetry code: (i) .