2-(4,5-Di-chloro-2-nitro-phen-yl)-4-meth-oxy-3-methyl-9-phenyl-sulfon-yl-9H-carbazole.

In the title compound, C26H18Cl2N2O5S, the carbazole ring system is essentially planar with a maximum deviation of 0.0498 (16) Å for the N atom. The carbazole ring system is almost orthogonal to the phenyl-sulfonyl and di-chloro-substituted nitro-phenyl rings, making dihedral angles of 84.23 (7) and 85.46 (12)°, respectively. The mol-ecular structure features intra-molecular C-H⋯O inter-actions, which generate two S(6) ring motifs. In the crystal, mol-ecules are linked by C-Cl⋯O halogen bonds [3.016 (3) Å, 166.63 (5)°], which generate infinite C(8) chains running parallel to [010].

Related literature

For the biological activity and uses of carbazole derivatives, see: Itoigawa et al. (2000 ▶); Ramsewak et al. (1999 ▶). For their electronic properties and applications, see: Friend et al. (1999 ▶); Zhang et al. (2004 ▶). For a related structure, see: Gopinath et al. (2013 ▶). For the Thorpe–Ingold effect, see: Bassindale et al. (1984 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H18Cl2N2O5S

M = 541.39

Monoclinic,

a = 18.6364 (7) Å

b = 12.1665 (4) Å

c = 21.1272 (7) Å

β = 91.461 (2)°

V = 4788.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.40 mm−1

T = 296 K

0.25 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.905, T max = 0.923

23543 measured reflections

5218 independent reflections

4056 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.112

S = 1.03

5218 reflections

327 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814001342/rk2420sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001342/rk2420Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001342/rk2420Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C26H18Cl2N2O5S	F(000) = 2224
Mr = 541.39	Dx = 1.502 Mg m−3
Monoclinic, C2/c	Melting point = 493–495 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 18.6364 (7) Å	Cell parameters from 4058 reflections
b = 12.1665 (4) Å	θ = 2.0–27.0°
c = 21.1272 (7) Å	µ = 0.40 mm−1
β = 91.461 (2)°	T = 296 K
V = 4788.8 (3) Å3	Block, colourless
Z = 8	0.25 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	5218 independent reflections
Radiation source: fine-focus sealed tube	4056 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω– and φ–scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −23→23
Tmin = 0.905, Tmax = 0.923	k = −15→15
23543 measured reflections	l = −26→26

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0583P)2 + 2.8891P] where P = (Fo2 + 2Fc2)/3
5218 reflections	(Δ/σ)max = 0.001
327 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.30233 (10)	0.60315 (14)	0.46304 (8)	0.0376 (4)
C2	0.31928 (12)	0.59976 (18)	0.39942 (9)	0.0508 (5)
H2	0.2838	0.6021	0.3677	0.061*
C3	0.39066 (13)	0.59284 (19)	0.38525 (10)	0.0573 (6)
H3	0.4035	0.5891	0.3430	0.069*
C4	0.44365 (12)	0.59128 (18)	0.43162 (11)	0.0539 (5)
H4	0.4915	0.5875	0.4202	0.065*
C5	0.42723 (10)	0.59515 (16)	0.49463 (9)	0.0434 (4)
H5	0.4633	0.5941	0.5259	0.052*
C6	0.35545 (9)	0.60060 (13)	0.51051 (8)	0.0338 (4)
C7	0.32037 (9)	0.60416 (13)	0.57063 (8)	0.0321 (3)
C8	0.34576 (9)	0.60187 (14)	0.63289 (8)	0.0347 (4)
C9	0.29861 (9)	0.60208 (14)	0.68281 (8)	0.0360 (4)
C10	0.22473 (9)	0.60638 (14)	0.66796 (8)	0.0353 (4)
C11	0.19794 (9)	0.61140 (15)	0.60641 (9)	0.0375 (4)
H11	0.1489	0.6162	0.5978	0.045*
C12	0.24651 (9)	0.60903 (13)	0.55824 (8)	0.0333 (4)
C13	0.17149 (9)	0.61156 (15)	0.71942 (8)	0.0367 (4)
C14	0.15400 (10)	0.71305 (15)	0.74444 (8)	0.0398 (4)
H14	0.1787	0.7750	0.7313	0.048*
C15	0.10101 (10)	0.72501 (15)	0.78834 (8)	0.0393 (4)
C16	0.06477 (9)	0.63314 (16)	0.81004 (8)	0.0384 (4)
C17	0.07991 (9)	0.53179 (16)	0.78529 (9)	0.0408 (4)
H17	0.0550	0.4699	0.7983	0.049*
C18	0.13256 (10)	0.52280 (15)	0.74091 (9)	0.0388 (4)
C19	0.15457 (11)	0.42952 (17)	0.46831 (10)	0.0504 (5)
C20	0.19244 (13)	0.36252 (19)	0.42797 (13)	0.0632 (6)
H20	0.2196	0.3928	0.3960	0.076*
C21	0.18912 (18)	0.2500 (2)	0.43609 (19)	0.0933 (11)
H21	0.2144	0.2038	0.4095	0.112*
C22	0.1490 (2)	0.2064 (3)	0.4828 (2)	0.1137 (15)
H22	0.1465	0.1305	0.4876	0.136*
C23	0.1125 (2)	0.2727 (3)	0.5224 (2)	0.1109 (13)
H23	0.0859	0.2421	0.5546	0.133*
C24	0.11478 (17)	0.3856 (2)	0.51522 (14)	0.0790 (8)
H24	0.0894	0.4310	0.5421	0.095*
C25	0.32572 (11)	0.59430 (18)	0.75030 (9)	0.0488 (5)
H25A	0.3757	0.5753	0.7510	0.073*
H25B	0.2992	0.5388	0.7720	0.073*
H25C	0.3195	0.6638	0.7709	0.073*
C26	0.45504 (12)	0.6937 (2)	0.65493 (13)	0.0670 (7)
H26A	0.4489	0.7400	0.6184	0.101*
H26B	0.5052	0.6799	0.6626	0.101*
H26C	0.4355	0.7295	0.6911	0.101*
N1	0.23420 (8)	0.61223 (12)	0.49177 (7)	0.0379 (3)
N2	0.14522 (10)	0.41316 (14)	0.71521 (9)	0.0547 (4)
O1	0.10190 (8)	0.62053 (13)	0.49305 (8)	0.0582 (4)
O2	0.16291 (9)	0.59563 (13)	0.39235 (7)	0.0590 (4)
O3	0.20623 (10)	0.38349 (14)	0.70792 (11)	0.0838 (6)
O4	0.09295 (11)	0.35658 (15)	0.70249 (11)	0.0870 (6)
O5	0.41857 (6)	0.59176 (11)	0.64406 (6)	0.0428 (3)
S1	0.15720 (3)	0.57206 (4)	0.45772 (2)	0.04322 (14)
Cl1	0.08048 (3)	0.85490 (4)	0.81386 (3)	0.05761 (16)
Cl2	0.00173 (3)	0.64492 (5)	0.86734 (2)	0.05700 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0450 (10)	0.0334 (9)	0.0349 (9)	−0.0025 (7)	0.0085 (8)	0.0000 (7)
C2	0.0599 (13)	0.0586 (13)	0.0339 (10)	−0.0034 (10)	0.0054 (9)	0.0013 (8)
C3	0.0698 (15)	0.0659 (14)	0.0371 (11)	0.0007 (11)	0.0208 (10)	0.0041 (10)
C4	0.0507 (12)	0.0614 (13)	0.0508 (12)	0.0030 (9)	0.0243 (10)	0.0079 (10)
C5	0.0392 (10)	0.0472 (11)	0.0446 (11)	0.0025 (8)	0.0130 (8)	0.0073 (8)
C6	0.0398 (9)	0.0281 (8)	0.0340 (9)	−0.0001 (6)	0.0093 (7)	0.0018 (6)
C7	0.0335 (9)	0.0285 (8)	0.0345 (9)	−0.0007 (6)	0.0069 (7)	−0.0003 (6)
C8	0.0323 (9)	0.0323 (9)	0.0396 (9)	0.0011 (6)	0.0048 (7)	0.0018 (7)
C9	0.0375 (9)	0.0367 (9)	0.0341 (9)	0.0014 (7)	0.0053 (7)	0.0002 (7)
C10	0.0358 (9)	0.0333 (9)	0.0371 (9)	0.0002 (7)	0.0092 (7)	−0.0008 (7)
C11	0.0308 (9)	0.0411 (10)	0.0408 (10)	0.0002 (7)	0.0048 (7)	−0.0038 (7)
C12	0.0365 (9)	0.0314 (8)	0.0321 (9)	−0.0005 (6)	0.0031 (7)	−0.0017 (6)
C13	0.0347 (9)	0.0424 (10)	0.0333 (9)	0.0027 (7)	0.0056 (7)	0.0011 (7)
C14	0.0409 (10)	0.0411 (10)	0.0378 (10)	−0.0016 (7)	0.0112 (8)	0.0000 (7)
C15	0.0386 (9)	0.0455 (10)	0.0341 (9)	0.0034 (7)	0.0059 (7)	−0.0029 (7)
C16	0.0278 (8)	0.0575 (12)	0.0301 (9)	0.0015 (7)	0.0035 (7)	0.0003 (8)
C17	0.0334 (9)	0.0480 (11)	0.0411 (10)	−0.0046 (7)	0.0014 (8)	0.0074 (8)
C18	0.0361 (9)	0.0413 (10)	0.0391 (10)	0.0024 (7)	0.0045 (7)	0.0024 (7)
C19	0.0496 (12)	0.0459 (11)	0.0549 (12)	−0.0075 (8)	−0.0154 (10)	−0.0018 (9)
C20	0.0598 (14)	0.0521 (14)	0.0764 (16)	0.0053 (10)	−0.0227 (12)	−0.0114 (11)
C21	0.090 (2)	0.0527 (17)	0.134 (3)	0.0128 (14)	−0.053 (2)	−0.0278 (17)
C22	0.132 (3)	0.0504 (19)	0.155 (4)	−0.021 (2)	−0.068 (3)	0.013 (2)
C23	0.131 (3)	0.083 (3)	0.117 (3)	−0.054 (2)	−0.020 (3)	0.034 (2)
C24	0.091 (2)	0.0693 (17)	0.0765 (18)	−0.0285 (14)	−0.0045 (15)	0.0078 (13)
C25	0.0492 (12)	0.0635 (13)	0.0340 (10)	0.0033 (9)	0.0043 (9)	0.0026 (9)
C26	0.0422 (12)	0.0717 (16)	0.0870 (18)	−0.0142 (10)	−0.0034 (12)	0.0007 (13)
N1	0.0368 (8)	0.0445 (8)	0.0325 (8)	−0.0025 (6)	0.0025 (6)	−0.0024 (6)
N2	0.0576 (11)	0.0413 (10)	0.0659 (12)	−0.0001 (8)	0.0158 (9)	0.0014 (8)
O1	0.0407 (8)	0.0681 (10)	0.0655 (10)	0.0108 (7)	−0.0047 (7)	−0.0103 (7)
O2	0.0667 (10)	0.0666 (10)	0.0429 (8)	−0.0010 (7)	−0.0159 (7)	0.0057 (7)
O3	0.0677 (12)	0.0498 (10)	0.1355 (18)	0.0124 (8)	0.0353 (12)	−0.0033 (10)
O4	0.0775 (13)	0.0578 (11)	0.1262 (17)	−0.0173 (9)	0.0093 (12)	−0.0258 (10)
O5	0.0310 (6)	0.0498 (8)	0.0477 (8)	0.0013 (5)	0.0021 (6)	0.0047 (6)
S1	0.0422 (3)	0.0440 (3)	0.0430 (3)	0.00159 (18)	−0.0079 (2)	−0.00157 (19)
Cl1	0.0647 (4)	0.0520 (3)	0.0571 (3)	0.0080 (2)	0.0205 (3)	−0.0108 (2)
Cl2	0.0392 (3)	0.0869 (4)	0.0457 (3)	−0.0042 (2)	0.0174 (2)	−0.0040 (2)

C1—C6	1.391 (3)	C16—C17	1.372 (3)
C1—C2	1.389 (3)	C16—Cl2	1.7144 (18)
C1—N1	1.426 (2)	C17—C18	1.379 (3)
C2—C3	1.373 (3)	C17—H17	0.9300
C2—H2	0.9300	C18—N2	1.462 (2)
C3—C4	1.373 (3)	C19—C24	1.362 (4)
C3—H3	0.9300	C19—C20	1.385 (3)
C4—C5	1.374 (3)	C19—S1	1.749 (2)
C4—H4	0.9300	C20—C21	1.382 (4)
C5—C6	1.389 (2)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.361 (6)
C6—C7	1.444 (2)	C21—H21	0.9300
C7—C8	1.387 (2)	C22—C23	1.358 (6)
C7—C12	1.396 (2)	C22—H22	0.9300
C8—O5	1.377 (2)	C23—C24	1.382 (4)
C8—C9	1.390 (2)	C23—H23	0.9300
C9—C10	1.405 (2)	C24—H24	0.9300
C9—C25	1.503 (3)	C25—H25A	0.9600
C10—C11	1.382 (3)	C25—H25B	0.9600
C10—C13	1.492 (2)	C25—H25C	0.9600
C11—C12	1.379 (2)	C26—O5	1.430 (3)
C11—H11	0.9300	C26—H26A	0.9600
C12—N1	1.418 (2)	C26—H26B	0.9600
C13—C18	1.384 (3)	C26—H26C	0.9600
C13—C14	1.385 (3)	N1—S1	1.6623 (15)
C14—C15	1.380 (2)	N2—O3	1.207 (2)
C14—H14	0.9300	N2—O4	1.217 (2)
C15—C16	1.390 (3)	O1—S1	1.4163 (16)
C15—Cl1	1.7161 (19)	O2—S1	1.4173 (16)
C6—C1—C2	121.43 (18)	C16—C17—H17	120.4
C6—C1—N1	108.66 (15)	C18—C17—H17	120.4
C2—C1—N1	129.89 (18)	C17—C18—C13	123.32 (17)
C3—C2—C1	117.3 (2)	C17—C18—N2	116.71 (17)
C3—C2—H2	121.4	C13—C18—N2	119.95 (17)
C1—C2—H2	121.4	C24—C19—C20	120.8 (2)
C2—C3—C4	121.9 (2)	C24—C19—S1	120.0 (2)
C2—C3—H3	119.1	C20—C19—S1	119.23 (19)
C4—C3—H3	119.1	C21—C20—C19	118.8 (3)
C3—C4—C5	121.1 (2)	C21—C20—H20	120.6
C3—C4—H4	119.4	C19—C20—H20	120.6
C5—C4—H4	119.4	C22—C21—C20	120.2 (3)
C4—C5—C6	118.37 (19)	C22—C21—H21	119.9
C4—C5—H5	120.8	C20—C21—H21	119.9
C6—C5—H5	120.8	C21—C22—C23	120.6 (3)
C5—C6—C1	119.93 (17)	C21—C22—H22	119.7
C5—C6—C7	132.40 (17)	C23—C22—H22	119.7
C1—C6—C7	107.67 (15)	C22—C23—C24	120.4 (4)
C8—C7—C12	119.32 (15)	C22—C23—H23	119.8
C8—C7—C6	133.05 (16)	C24—C23—H23	119.8
C12—C7—C6	107.63 (15)	C19—C24—C23	119.3 (3)
O5—C8—C7	118.38 (15)	C19—C24—H24	120.4
O5—C8—C9	120.63 (16)	C23—C24—H24	120.4
C7—C8—C9	120.84 (16)	C9—C25—H25A	109.5
C8—C9—C10	117.74 (16)	C9—C25—H25B	109.5
C8—C9—C25	121.05 (16)	H25A—C25—H25B	109.5
C10—C9—C25	121.18 (16)	C9—C25—H25C	109.5
C11—C10—C9	122.69 (16)	H25A—C25—H25C	109.5
C11—C10—C13	116.92 (15)	H25B—C25—H25C	109.5
C9—C10—C13	120.32 (16)	O5—C26—H26A	109.5
C12—C11—C10	117.71 (16)	O5—C26—H26B	109.5
C12—C11—H11	121.1	H26A—C26—H26B	109.5
C10—C11—H11	121.1	O5—C26—H26C	109.5
C11—C12—C7	121.67 (16)	H26A—C26—H26C	109.5
C11—C12—N1	129.61 (16)	H26B—C26—H26C	109.5
C7—C12—N1	108.72 (15)	C12—N1—C1	107.23 (14)
C18—C13—C14	116.10 (16)	C12—N1—S1	122.47 (12)
C18—C13—C10	124.76 (16)	C1—N1—S1	124.15 (12)
C14—C13—C10	118.88 (16)	O3—N2—O4	123.7 (2)
C15—C14—C13	122.00 (17)	O3—N2—C18	118.82 (18)
C15—C14—H14	119.0	O4—N2—C18	117.53 (19)
C13—C14—H14	119.0	C8—O5—C26	114.36 (15)
C14—C15—C16	119.94 (17)	O2—S1—O1	120.21 (10)
C14—C15—Cl1	118.53 (14)	O2—S1—N1	106.07 (9)
C16—C15—Cl1	121.52 (14)	O1—S1—N1	106.33 (8)
C17—C16—C15	119.40 (17)	O2—S1—C19	109.16 (10)
C17—C16—Cl2	119.72 (15)	O1—S1—C19	108.80 (11)
C15—C16—Cl2	120.88 (15)	N1—S1—C19	105.23 (9)
C16—C17—C18	119.17 (17)
C6—C1—C2—C3	0.5 (3)	C14—C15—C16—Cl2	176.85 (14)
N1—C1—C2—C3	178.70 (19)	Cl1—C15—C16—Cl2	−4.3 (2)
C1—C2—C3—C4	−1.2 (3)	C15—C16—C17—C18	2.2 (3)
C2—C3—C4—C5	0.9 (3)	Cl2—C16—C17—C18	−177.65 (13)
C3—C4—C5—C6	0.1 (3)	C16—C17—C18—C13	−0.2 (3)
C4—C5—C6—C1	−0.6 (3)	C16—C17—C18—N2	−178.70 (17)
C4—C5—C6—C7	179.07 (19)	C14—C13—C18—C17	−1.0 (3)
C2—C1—C6—C5	0.3 (3)	C10—C13—C18—C17	−175.02 (17)
N1—C1—C6—C5	−178.16 (15)	C14—C13—C18—N2	177.48 (17)
C2—C1—C6—C7	−179.44 (17)	C10—C13—C18—N2	3.4 (3)
N1—C1—C6—C7	2.06 (18)	C24—C19—C20—C21	0.1 (3)
C5—C6—C7—C8	−1.0 (3)	S1—C19—C20—C21	−178.99 (18)
C1—C6—C7—C8	178.70 (18)	C19—C20—C21—C22	0.3 (4)
C5—C6—C7—C12	−179.87 (18)	C20—C21—C22—C23	−0.8 (5)
C1—C6—C7—C12	−0.12 (18)	C21—C22—C23—C24	1.0 (5)
C12—C7—C8—O5	176.94 (14)	C20—C19—C24—C23	0.1 (4)
C6—C7—C8—O5	−1.8 (3)	S1—C19—C24—C23	179.2 (2)
C12—C7—C8—C9	1.3 (2)	C22—C23—C24—C19	−0.7 (5)
C6—C7—C8—C9	−177.38 (17)	C11—C12—N1—C1	−177.70 (17)
O5—C8—C9—C10	−176.46 (15)	C7—C12—N1—C1	3.11 (18)
C7—C8—C9—C10	−0.9 (2)	C11—C12—N1—S1	−24.3 (3)
O5—C8—C9—C25	1.6 (3)	C7—C12—N1—S1	156.49 (12)
C7—C8—C9—C25	177.13 (17)	C6—C1—N1—C12	−3.19 (18)
C8—C9—C10—C11	−0.6 (3)	C2—C1—N1—C12	178.47 (19)
C25—C9—C10—C11	−178.71 (17)	C6—C1—N1—S1	−156.01 (13)
C8—C9—C10—C13	−177.44 (16)	C2—C1—N1—S1	25.7 (3)
C25—C9—C10—C13	4.5 (3)	C17—C18—N2—O3	−138.2 (2)
C9—C10—C11—C12	1.8 (3)	C13—C18—N2—O3	43.3 (3)
C13—C10—C11—C12	178.68 (16)	C17—C18—N2—O4	41.6 (3)
C10—C11—C12—C7	−1.4 (3)	C13—C18—N2—O4	−136.9 (2)
C10—C11—C12—N1	179.54 (16)	C7—C8—O5—C26	96.3 (2)
C8—C7—C12—C11	−0.1 (2)	C9—C8—O5—C26	−88.1 (2)
C6—C7—C12—C11	178.87 (16)	C12—N1—S1—O2	175.29 (14)
C8—C7—C12—N1	179.12 (14)	C1—N1—S1—O2	−35.85 (17)
C6—C7—C12—N1	−1.87 (18)	C12—N1—S1—O1	46.24 (16)
C11—C10—C13—C18	82.6 (2)	C1—N1—S1—O1	−164.90 (15)
C9—C10—C13—C18	−100.5 (2)	C12—N1—S1—C19	−69.08 (16)
C11—C10—C13—C14	−91.3 (2)	C1—N1—S1—C19	79.77 (16)
C9—C10—C13—C14	85.6 (2)	C24—C19—S1—O2	−146.25 (19)
C18—C13—C14—C15	0.1 (3)	C20—C19—S1—O2	32.82 (19)
C10—C13—C14—C15	174.57 (16)	C24—C19—S1—O1	−13.3 (2)
C13—C14—C15—C16	1.8 (3)	C20—C19—S1—O1	165.73 (16)
C13—C14—C15—Cl1	−177.08 (14)	C24—C19—S1—N1	100.3 (2)
C14—C15—C16—C17	−3.0 (3)	C20—C19—S1—N1	−80.66 (17)
Cl1—C15—C16—C17	175.87 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.33	2.915 (3)	121
C11—H11···O1	0.93	2.36	2.955 (2)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2	0.93	2.33	2.915 (3)	121
C11—H11⋯O1	0.93	2.36	2.955 (2)	122