2-(4-Chloro-2-nitro-phen-yl)-4-meth-oxy-9-phenyl-sulfonyl-9H-carbazole-3-carbaldehyde.

In the sterically hindered title compound, C26H17ClN2O6S, the carbazole ring has a maximum deviation from planarity of 0.067 (4) Å for the C atom connected to the aldehyde group. The carbazole moiety forms a dihedral angle of 72.8 (1)° with the nitro-substituted benzene ring. The O atom of the meth-oxy group deviates by 0.186 (1) Å from the adjacent carbazole moiety. The phenyl-sulfonyl group forms intra-molecular C-H⋯O bonds between sulfone O atoms and the carbazole moiety, resulting in two S(6) rings. In the crystal, the nitrated benzene rings are linked via C-H⋯O inter-actions forming infinite C(7) chains along [100]. The crystal packing is also characterized by C-H⋯π inter-actions, which result in inversion dimers.

Related literature

For the biological activities 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 related structures, see: Gopinath et al.(2013 ▶). For the Thorpe–Ingold effect, see: Bassindale (1984 ▶). For bond-length distortions, see: Allen et al. (1987 ▶). For graph-set notation: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H17ClN2O6S

M = 520.94

Triclinic,

a = 8.1937 (5) Å

b = 11.6112 (8) Å

c = 12.4346 (9) Å

α = 93.886 (2)°

β = 93.952 (3)°

γ = 97.772 (2)°

V = 1165.80 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.30 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 = 0.928, T max = 0.942

20355 measured reflections

4582 independent reflections

3911 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.152

S = 1.04

4582 reflections

326 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.00 e Å−3

Δρmin = −0.55 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/S1600536814001809/ld2117sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001809/ld2117Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001809/ld2117Isup3.cml

CCDC reference:

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

C26H17ClN2O6S	Z = 2
Mr = 520.94	F(000) = 536
Triclinic, P1	Dx = 1.484 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1937 (5) Å	Cell parameters from 3911 reflections
b = 11.6112 (8) Å	θ = 1.7–26.0°
c = 12.4346 (9) Å	µ = 0.30 mm−1
α = 93.886 (2)°	T = 296 K
β = 93.952 (3)°	Block, colourless
γ = 97.772 (2)°	0.25 × 0.25 × 0.20 mm
V = 1165.80 (14) Å3

Bruker Kappa APEXII CCD diffractometer	4582 independent reflections
Radiation source: fine-focus sealed tube	3911 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω & φ scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.928, Tmax = 0.942	k = −14→14
20355 measured reflections	l = −15→15

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.066P)2 + 1.5141P] where P = (Fo2 + 2Fc2)/3
4582 reflections	(Δ/σ)max = 0.004
326 parameters	Δρmax = 1.00 e Å−3
1 restraint	Δρmin = −0.55 e Å−3

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
C1	0.7875 (3)	1.0463 (2)	0.4054 (2)	0.0331 (5)
C2	0.7602 (4)	1.1615 (2)	0.4210 (2)	0.0434 (6)
H2	0.7825	1.2139	0.3689	0.052*
C3	0.6986 (4)	1.1949 (3)	0.5170 (3)	0.0484 (7)
H3	0.6789	1.2715	0.5295	0.058*
C4	0.6655 (4)	1.1179 (3)	0.5950 (2)	0.0519 (7)
H4	0.6244	1.1434	0.6589	0.062*
C5	0.6926 (4)	1.0039 (3)	0.5794 (2)	0.0502 (7)
H5	0.6696	0.9521	0.6321	0.060*
C6	0.7551 (3)	0.9672 (2)	0.4836 (2)	0.0372 (6)
C7	0.7947 (3)	0.8559 (2)	0.4413 (2)	0.0378 (6)
C8	0.7786 (5)	0.7452 (3)	0.4785 (3)	0.0550 (8)
C9	0.8216 (5)	0.6511 (3)	0.4157 (3)	0.0541 (8)
C10	0.8860 (3)	0.6700 (2)	0.3155 (2)	0.0384 (6)
C11	0.9044 (3)	0.7800 (2)	0.2777 (2)	0.0344 (5)
H11	0.9494	0.7928	0.2121	0.041*
C12	0.8542 (3)	0.8706 (2)	0.3397 (2)	0.0313 (5)
C13	0.9424 (3)	0.5760 (2)	0.2451 (2)	0.0379 (6)
C14	1.1098 (4)	0.5799 (2)	0.2345 (3)	0.0457 (7)
H14	1.1822	0.6399	0.2725	0.055*
C15	1.1740 (4)	0.4983 (3)	0.1700 (3)	0.0500 (7)
H15	1.2874	0.5035	0.1646	0.060*
C16	1.0675 (4)	0.4088 (2)	0.1134 (2)	0.0424 (6)
C17	0.9005 (4)	0.4010 (2)	0.1208 (2)	0.0451 (7)
H17	0.8286	0.3403	0.0835	0.054*
C18	0.8413 (3)	0.4851 (2)	0.1845 (3)	0.0434 (6)
C19	0.6070 (3)	0.9713 (2)	0.15423 (19)	0.0343 (5)
C20	0.4916 (4)	1.0486 (3)	0.1531 (2)	0.0440 (6)
H20	0.5234	1.1277	0.1722	0.053*
C21	0.3274 (4)	1.0045 (3)	0.1228 (3)	0.0544 (8)
H21	0.2482	1.0548	0.1215	0.065*
C22	0.2810 (4)	0.8885 (3)	0.0951 (2)	0.0535 (8)
H22	0.1708	0.8605	0.0744	0.064*
C23	0.3965 (4)	0.8121 (3)	0.0974 (3)	0.0516 (7)
H23	0.3636	0.7329	0.0793	0.062*
C24	0.5606 (4)	0.8532 (2)	0.1265 (2)	0.0419 (6)
H24	0.6391	0.8023	0.1275	0.050*
C25	0.8105 (7)	0.7460 (5)	0.6582 (5)	0.1012 (16)
H25A	0.8853	0.6893	0.6552	0.152*
H25B	0.7546	0.7410	0.7234	0.152*
H25C	0.8712	0.8227	0.6572	0.152*
C26	0.7960 (8)	0.5343 (3)	0.4572 (4)	0.1036 (19)
H26	0.7534	0.5295	0.5245	0.124*
N1	0.8522 (3)	0.98826 (17)	0.31621 (17)	0.0342 (5)
N2	0.6608 (4)	0.4752 (3)	0.1854 (3)	0.0768 (10)
O1	0.8401 (3)	1.14723 (16)	0.19275 (16)	0.0466 (5)
O2	0.9140 (2)	0.95808 (17)	0.12450 (15)	0.0428 (5)
O3	0.5979 (3)	0.5591 (3)	0.2093 (3)	0.1015 (12)
O4	0.5802 (4)	0.3792 (3)	0.1634 (5)	0.154 (2)
O5	0.6999 (4)	0.7255 (2)	0.5730 (2)	0.0744 (8)
O6	0.8242 (7)	0.4466 (2)	0.4137 (3)	0.141 (2)
S1	0.81663 (8)	1.02362 (5)	0.18874 (5)	0.03341 (18)
Cl1	1.14424 (12)	0.30394 (8)	0.03361 (7)	0.0654 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0332 (13)	0.0314 (12)	0.0331 (12)	0.0020 (10)	0.0000 (10)	−0.0008 (10)
C2	0.0545 (17)	0.0313 (13)	0.0444 (15)	0.0062 (12)	0.0046 (13)	0.0021 (11)
C3	0.0570 (18)	0.0357 (14)	0.0514 (17)	0.0095 (13)	0.0009 (14)	−0.0090 (12)
C4	0.065 (2)	0.0505 (17)	0.0398 (15)	0.0098 (15)	0.0102 (14)	−0.0083 (13)
C5	0.070 (2)	0.0471 (16)	0.0356 (14)	0.0105 (14)	0.0122 (14)	0.0028 (12)
C6	0.0422 (15)	0.0345 (13)	0.0344 (13)	0.0054 (11)	0.0000 (11)	0.0011 (10)
C7	0.0462 (15)	0.0342 (13)	0.0338 (13)	0.0078 (11)	0.0039 (11)	0.0030 (10)
C8	0.083 (2)	0.0384 (15)	0.0467 (15)	0.0128 (15)	0.0127 (14)	0.0115 (12)
C9	0.083 (2)	0.0346 (15)	0.0483 (17)	0.0134 (15)	0.0137 (16)	0.0107 (12)
C10	0.0424 (15)	0.0315 (13)	0.0416 (14)	0.0068 (11)	0.0011 (11)	0.0029 (11)
C11	0.0380 (14)	0.0317 (12)	0.0340 (13)	0.0063 (10)	0.0037 (10)	0.0029 (10)
C12	0.0321 (12)	0.0287 (12)	0.0330 (12)	0.0039 (9)	−0.0002 (10)	0.0051 (9)
C13	0.0414 (15)	0.0288 (12)	0.0437 (14)	0.0078 (10)	−0.0013 (11)	0.0041 (10)
C14	0.0398 (15)	0.0381 (14)	0.0562 (17)	0.0025 (12)	−0.0049 (13)	−0.0029 (12)
C15	0.0375 (15)	0.0467 (16)	0.067 (2)	0.0091 (12)	0.0048 (14)	0.0014 (14)
C16	0.0503 (17)	0.0363 (14)	0.0434 (15)	0.0147 (12)	0.0053 (12)	0.0043 (11)
C17	0.0487 (17)	0.0332 (14)	0.0514 (17)	0.0059 (12)	−0.0034 (13)	−0.0032 (12)
C18	0.0374 (15)	0.0356 (14)	0.0565 (17)	0.0063 (11)	0.0004 (12)	−0.0007 (12)
C19	0.0346 (13)	0.0411 (14)	0.0287 (12)	0.0080 (10)	0.0058 (10)	0.0048 (10)
C20	0.0466 (16)	0.0479 (16)	0.0408 (15)	0.0157 (13)	0.0076 (12)	0.0052 (12)
C21	0.0412 (17)	0.081 (2)	0.0471 (17)	0.0253 (16)	0.0075 (13)	0.0091 (16)
C22	0.0366 (16)	0.080 (2)	0.0419 (16)	0.0023 (15)	0.0028 (12)	0.0049 (15)
C23	0.0493 (18)	0.0541 (18)	0.0470 (17)	−0.0043 (14)	0.0021 (13)	−0.0020 (13)
C24	0.0422 (15)	0.0421 (15)	0.0416 (15)	0.0069 (12)	0.0037 (12)	0.0021 (11)
C25	0.092 (4)	0.086 (3)	0.125 (5)	0.022 (3)	−0.014 (3)	0.007 (3)
C26	0.204 (6)	0.043 (2)	0.076 (3)	0.030 (3)	0.057 (3)	0.0231 (19)
N1	0.0417 (12)	0.0282 (10)	0.0333 (11)	0.0057 (9)	0.0041 (9)	0.0042 (8)
N2	0.0408 (16)	0.0591 (18)	0.124 (3)	0.0025 (14)	0.0016 (17)	−0.0289 (19)
O1	0.0576 (13)	0.0341 (10)	0.0481 (11)	0.0005 (9)	0.0046 (9)	0.0139 (8)
O2	0.0412 (10)	0.0512 (11)	0.0402 (10)	0.0128 (9)	0.0144 (8)	0.0102 (8)
O3	0.0417 (14)	0.081 (2)	0.174 (3)	0.0164 (13)	−0.0013 (17)	−0.047 (2)
O4	0.0548 (19)	0.092 (3)	0.296 (6)	−0.0152 (17)	0.022 (3)	−0.077 (3)
O5	0.116 (2)	0.0623 (15)	0.0496 (13)	0.0163 (15)	0.0204 (14)	0.0153 (11)
O6	0.301 (6)	0.0359 (15)	0.105 (3)	0.040 (2)	0.090 (3)	0.0241 (15)
S1	0.0359 (3)	0.0318 (3)	0.0338 (3)	0.0044 (2)	0.0069 (2)	0.0082 (2)
Cl1	0.0788 (6)	0.0592 (5)	0.0625 (5)	0.0269 (4)	0.0160 (4)	−0.0087 (4)

C1—C2	1.388 (4)	C16—C17	1.369 (4)
C1—C6	1.396 (4)	C16—Cl1	1.730 (3)
C1—N1	1.429 (3)	C17—C18	1.375 (4)
C2—C3	1.380 (4)	C17—H17	0.9300
C2—H2	0.9300	C18—N2	1.469 (4)
C3—C4	1.379 (4)	C19—C24	1.386 (4)
C3—H3	0.9300	C19—C20	1.389 (4)
C4—C5	1.375 (4)	C19—S1	1.756 (3)
C4—H4	0.9300	C20—C21	1.390 (4)
C5—C6	1.391 (4)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.364 (5)
C6—C7	1.449 (4)	C21—H21	0.9300
C7—C8	1.389 (4)	C22—C23	1.382 (5)
C7—C12	1.398 (4)	C22—H22	0.9300
C8—O5	1.396 (4)	C23—C24	1.380 (4)
C8—C9	1.398 (4)	C23—H23	0.9300
C9—C10	1.406 (4)	C24—H24	0.9300
C9—C26	1.477 (5)	C25—O5	1.332 (6)
C10—C11	1.384 (4)	C25—H25A	0.9600
C10—C13	1.494 (4)	C25—H25B	0.9600
C11—C12	1.387 (3)	C25—H25C	0.9600
C11—H11	0.9300	C26—O6	1.178 (5)
C12—N1	1.418 (3)	C26—H26	0.9300
C13—C14	1.382 (4)	N1—S1	1.680 (2)
C13—C18	1.392 (4)	N2—O3	1.193 (4)
C14—C15	1.382 (4)	N2—O4	1.220 (4)
C14—H14	0.9300	O1—S1	1.4191 (19)
C15—C16	1.380 (4)	O2—S1	1.4226 (19)
C15—H15	0.9300
C2—C1—C6	121.7 (2)	C15—C16—Cl1	120.2 (2)
C2—C1—N1	129.6 (2)	C16—C17—C18	118.5 (3)
C6—C1—N1	108.7 (2)	C16—C17—H17	120.8
C3—C2—C1	117.3 (3)	C18—C17—H17	120.8
C3—C2—H2	121.4	C17—C18—C13	123.6 (3)
C1—C2—H2	121.4	C17—C18—N2	116.1 (3)
C4—C3—C2	121.8 (3)	C13—C18—N2	120.3 (3)
C4—C3—H3	119.1	C24—C19—C20	121.3 (3)
C2—C3—H3	119.1	C24—C19—S1	118.9 (2)
C5—C4—C3	120.8 (3)	C20—C19—S1	119.8 (2)
C5—C4—H4	119.6	C19—C20—C21	118.2 (3)
C3—C4—H4	119.6	C19—C20—H20	120.9
C4—C5—C6	118.9 (3)	C21—C20—H20	120.9
C4—C5—H5	120.5	C22—C21—C20	120.8 (3)
C6—C5—H5	120.5	C22—C21—H21	119.6
C5—C6—C1	119.5 (3)	C20—C21—H21	119.6
C5—C6—C7	133.1 (3)	C21—C22—C23	120.6 (3)
C1—C6—C7	107.4 (2)	C21—C22—H22	119.7
C8—C7—C12	118.4 (2)	C23—C22—H22	119.7
C8—C7—C6	133.6 (3)	C24—C23—C22	120.0 (3)
C12—C7—C6	107.9 (2)	C24—C23—H23	120.0
C7—C8—O5	119.2 (3)	C22—C23—H23	120.0
C7—C8—C9	120.5 (3)	C23—C24—C19	119.1 (3)
O5—C8—C9	119.8 (3)	C23—C24—H24	120.5
C8—C9—C10	119.4 (3)	C19—C24—H24	120.5
C8—C9—C26	118.3 (3)	O5—C25—H25A	109.5
C10—C9—C26	122.2 (3)	O5—C25—H25B	109.5
C11—C10—C9	120.8 (3)	H25A—C25—H25B	109.5
C11—C10—C13	116.0 (2)	O5—C25—H25C	109.5
C9—C10—C13	123.2 (2)	H25A—C25—H25C	109.5
C10—C11—C12	118.5 (2)	H25B—C25—H25C	109.5
C10—C11—H11	120.8	O6—C26—C9	126.5 (4)
C12—C11—H11	120.8	O6—C26—H26	116.7
C11—C12—C7	122.3 (2)	C9—C26—H26	116.7
C11—C12—N1	129.1 (2)	C12—N1—C1	107.4 (2)
C7—C12—N1	108.6 (2)	C12—N1—S1	121.09 (17)
C14—C13—C18	115.5 (3)	C1—N1—S1	121.81 (17)
C14—C13—C10	118.3 (2)	O3—N2—O4	122.1 (3)
C18—C13—C10	126.2 (3)	O3—N2—C18	119.9 (3)
C13—C14—C15	122.7 (3)	O4—N2—C18	118.0 (3)
C13—C14—H14	118.7	C25—O5—C8	109.6 (4)
C15—C14—H14	118.7	O1—S1—O2	120.52 (12)
C16—C15—C14	119.1 (3)	O1—S1—N1	106.44 (11)
C16—C15—H15	120.5	O2—S1—N1	105.99 (11)
C14—C15—H15	120.5	O1—S1—C19	109.19 (13)
C17—C16—C15	120.6 (3)	O2—S1—C19	108.75 (12)
C17—C16—Cl1	119.2 (2)	N1—S1—C19	104.80 (11)
C6—C1—C2—C3	−0.4 (4)	C15—C16—C17—C18	0.8 (4)
N1—C1—C2—C3	−178.8 (3)	Cl1—C16—C17—C18	−180.0 (2)
C1—C2—C3—C4	0.2 (5)	C16—C17—C18—C13	−2.2 (5)
C2—C3—C4—C5	−0.2 (5)	C16—C17—C18—N2	177.4 (3)
C3—C4—C5—C6	0.4 (5)	C14—C13—C18—C17	2.3 (4)
C4—C5—C6—C1	−0.5 (5)	C10—C13—C18—C17	179.8 (3)
C4—C5—C6—C7	−178.8 (3)	C14—C13—C18—N2	−177.2 (3)
C2—C1—C6—C5	0.6 (4)	C10—C13—C18—N2	0.2 (5)
N1—C1—C6—C5	179.3 (3)	C24—C19—C20—C21	−0.3 (4)
C2—C1—C6—C7	179.2 (2)	S1—C19—C20—C21	178.4 (2)
N1—C1—C6—C7	−2.1 (3)	C19—C20—C21—C22	0.1 (4)
C5—C6—C7—C8	3.1 (6)	C20—C21—C22—C23	0.5 (5)
C1—C6—C7—C8	−175.4 (3)	C21—C22—C23—C24	−0.9 (5)
C5—C6—C7—C12	180.0 (3)	C22—C23—C24—C19	0.6 (4)
C1—C6—C7—C12	1.6 (3)	C20—C19—C24—C23	0.0 (4)
C12—C7—C8—O5	−171.8 (3)	S1—C19—C24—C23	−178.8 (2)
C6—C7—C8—O5	4.8 (6)	C8—C9—C26—O6	179.1 (6)
C12—C7—C8—C9	0.2 (5)	C10—C9—C26—O6	−0.3 (9)
C6—C7—C8—C9	176.9 (3)	C11—C12—N1—C1	179.2 (2)
C7—C8—C9—C10	1.8 (5)	C7—C12—N1—C1	−0.8 (3)
O5—C8—C9—C10	173.8 (3)	C11—C12—N1—S1	32.7 (4)
C7—C8—C9—C26	−177.6 (4)	C7—C12—N1—S1	−147.29 (19)
O5—C8—C9—C26	−5.6 (6)	C2—C1—N1—C12	−179.6 (3)
C8—C9—C10—C11	−1.2 (5)	C6—C1—N1—C12	1.8 (3)
C26—C9—C10—C11	178.3 (4)	C2—C1—N1—S1	−33.4 (4)
C8—C9—C10—C13	177.2 (3)	C6—C1—N1—S1	147.99 (19)
C26—C9—C10—C13	−3.4 (6)	C17—C18—N2—O3	−157.0 (4)
C9—C10—C11—C12	−1.5 (4)	C13—C18—N2—O3	22.6 (6)
C13—C10—C11—C12	−180.0 (2)	C17—C18—N2—O4	24.4 (6)
C10—C11—C12—C7	3.6 (4)	C13—C18—N2—O4	−155.9 (5)
C10—C11—C12—N1	−176.4 (2)	C7—C8—O5—C25	−89.5 (4)
C8—C7—C12—C11	−3.0 (4)	C9—C8—O5—C25	98.3 (4)
C6—C7—C12—C11	179.5 (2)	C12—N1—S1—O1	−174.10 (19)
C8—C7—C12—N1	177.0 (3)	C1—N1—S1—O1	44.2 (2)
C6—C7—C12—N1	−0.4 (3)	C12—N1—S1—O2	−44.7 (2)
C11—C10—C13—C14	69.0 (3)	C1—N1—S1—O2	173.67 (19)
C9—C10—C13—C14	−109.5 (3)	C12—N1—S1—C19	70.3 (2)
C11—C10—C13—C18	−108.5 (3)	C1—N1—S1—C19	−71.4 (2)
C9—C10—C13—C18	73.1 (4)	C24—C19—S1—O1	168.4 (2)
C18—C13—C14—C15	−1.2 (4)	C20—C19—S1—O1	−10.4 (2)
C10—C13—C14—C15	−178.9 (3)	C24—C19—S1—O2	35.1 (2)
C13—C14—C15—C16	−0.1 (5)	C20—C19—S1—O2	−143.7 (2)
C14—C15—C16—C17	0.2 (5)	C24—C19—S1—N1	−77.9 (2)
C14—C15—C16—Cl1	−179.0 (2)	C20—C19—S1—N1	103.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.37	2.955 (3)	121
C11—H11···O2	0.93	2.31	2.902 (3)	121
C15—H15···O3i	0.93	2.55	3.444 (4)	161
C4—H4···Cg1ii	0.93	2.94	3.715 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C19–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.37	2.955 (3)	121
C11—H11⋯O2	0.93	2.31	2.902 (3)	121
C15—H15⋯O3i	0.93	2.55	3.444 (4)	161
C4—H4⋯Cg1ii	0.93	2.94	3.715 (3)	142

Symmetry codes: (i) ; (ii) .