5-Chloro-1-(4-methyl-phenyl-sulfon-yl)-1H-indole.

In the title compound, C15H12ClNO2S, the indole ring is essentially planar (r.m.s. deviation = 0.0107 Å) and makes a dihedral angle of 85.01 (6)° with the benzene ring. In the crystal, three C-H⋯O hydrogen bonds result in a hydrogen-bonded spiral running parallel to the c axis.

Related literature

For background to the use of indoles as scaffolds in the synthesis of HIV-agents, see: Hassam et al. (2012 ▶). For the crystal structure of a closely related compound, see: Beddoes et al. (1986 ▶).

Experimental

Crystal data

C15H12ClNO2S

M = 305.77

Tetragonal,

a = 26.991 (7) Å

c = 7.8345 (19) Å

V = 5708 (2) Å3

Z = 16

Mo Kα radiation

μ = 0.41 mm−1

T = 111 K

0.1 × 0.1 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.950, T max = 0.968

17940 measured reflections

3565 independent reflections

2760 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.101

S = 1.06

3565 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶; Atwood & Barbour, 2003 ▶); software used to prepare material for publication: X-SEED.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046466/pv2597sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046466/pv2597Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046466/pv2597Isup3.cml

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

C15H12ClNO2S	Dx = 1.423 Mg m−3
Mr = 305.77	Melting point: 383 K
Tetragonal, I41/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 4ad	Cell parameters from 3900 reflections
a = 26.991 (7) Å	θ = 3.0–25.8°
c = 7.8345 (19) Å	µ = 0.41 mm−1
V = 5708 (2) Å3	T = 111 K
Z = 16	Plate, colourless
F(000) = 2528	0.1 × 0.1 × 0.01 mm

Bruker APEXII CCD diffractometer	3565 independent reflections
Radiation source: fine-focus sealed tube, Bruker SMART APEXII	2760 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 28.9°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −36→26
Tmin = 0.950, Tmax = 0.968	k = −36→30
17940 measured reflections	l = −10→9

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0395P)2 + 5.9559P] where P = (Fo2 + 2Fc2)/3
3565 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.36 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
S1	0.309589 (17)	0.612848 (17)	0.38622 (6)	0.02904 (13)
Cl1	0.494357 (19)	0.67701 (2)	0.99440 (8)	0.04639 (17)
C9	0.27756 (6)	0.66717 (7)	0.4379 (2)	0.0244 (4)
N1	0.33623 (5)	0.59487 (5)	0.56768 (19)	0.0257 (3)
O2	0.27557 (6)	0.57429 (5)	0.34641 (19)	0.0423 (4)
C1	0.31014 (7)	0.56870 (7)	0.6945 (3)	0.0306 (4)
H1	0.2805	0.5505	0.6762	0.037*
C5	0.44798 (7)	0.65358 (7)	0.8611 (3)	0.0304 (4)
O1	0.34919 (5)	0.62485 (6)	0.27270 (16)	0.0384 (3)
C4	0.41247 (7)	0.62301 (7)	0.9286 (2)	0.0299 (4)
H4	0.4129	0.6143	1.0461	0.036*
C8	0.37656 (6)	0.61872 (6)	0.6465 (2)	0.0223 (3)
C6	0.44862 (7)	0.66693 (7)	0.6895 (3)	0.0321 (4)
H6	0.4741	0.6879	0.6477	0.039*
C7	0.41247 (7)	0.64987 (7)	0.5795 (2)	0.0282 (4)
H7	0.4122	0.6591	0.4625	0.034*
C3	0.37571 (6)	0.60502 (6)	0.8196 (2)	0.0245 (4)
C11	0.27459 (7)	0.75507 (7)	0.4642 (3)	0.0324 (4)
H11	0.2898	0.7865	0.4496	0.039*
C10	0.30006 (7)	0.71282 (7)	0.4162 (2)	0.0290 (4)
H10	0.3324	0.7151	0.3692	0.035*
C2	0.33347 (7)	0.57340 (7)	0.8452 (2)	0.0306 (4)
H2	0.3238	0.5585	0.9499	0.037*
C12	0.22732 (7)	0.75243 (7)	0.5330 (2)	0.0298 (4)
C14	0.23055 (7)	0.66336 (7)	0.5066 (3)	0.0325 (4)
H14	0.2155	0.6319	0.5215	0.039*
C13	0.20586 (7)	0.70613 (8)	0.5533 (3)	0.0343 (4)
H13	0.1735	0.7038	0.6002	0.041*
C15	0.19970 (8)	0.79851 (8)	0.5824 (3)	0.0417 (5)
H15A	0.1849	0.7940	0.6956	0.063*
H16B	0.1735	0.8050	0.4987	0.063*
H17C	0.2227	0.8266	0.5851	0.063*

	U11	U22	U33	U12	U13	U23
S1	0.0320 (3)	0.0321 (3)	0.0230 (2)	0.00953 (18)	−0.00349 (18)	−0.00451 (18)
Cl1	0.0310 (3)	0.0522 (3)	0.0560 (3)	0.0064 (2)	−0.0073 (2)	−0.0294 (3)
C9	0.0226 (8)	0.0297 (9)	0.0209 (8)	0.0049 (7)	−0.0012 (7)	−0.0012 (7)
N1	0.0264 (8)	0.0276 (8)	0.0231 (7)	0.0022 (6)	−0.0005 (6)	0.0019 (6)
O2	0.0480 (9)	0.0340 (8)	0.0448 (9)	0.0065 (6)	−0.0175 (7)	−0.0127 (7)
C1	0.0291 (10)	0.0247 (9)	0.0382 (10)	−0.0007 (7)	0.0041 (8)	0.0034 (8)
C5	0.0243 (9)	0.0296 (9)	0.0375 (10)	0.0075 (7)	−0.0022 (8)	−0.0120 (8)
O1	0.0414 (8)	0.0520 (9)	0.0218 (6)	0.0217 (7)	0.0058 (6)	0.0028 (6)
C4	0.0309 (10)	0.0356 (10)	0.0230 (9)	0.0116 (8)	0.0002 (7)	−0.0038 (8)
C8	0.0226 (8)	0.0221 (8)	0.0224 (8)	0.0063 (6)	0.0019 (7)	0.0009 (6)
C6	0.0243 (9)	0.0261 (9)	0.0460 (11)	0.0023 (7)	0.0051 (8)	−0.0002 (8)
C7	0.0268 (9)	0.0296 (9)	0.0283 (9)	0.0054 (7)	0.0062 (7)	0.0056 (7)
C3	0.0262 (9)	0.0243 (8)	0.0230 (8)	0.0079 (7)	0.0039 (7)	0.0019 (7)
C11	0.0338 (10)	0.0267 (9)	0.0368 (11)	0.0006 (8)	0.0011 (8)	0.0051 (8)
C10	0.0234 (9)	0.0347 (10)	0.0287 (9)	0.0025 (7)	0.0048 (7)	0.0051 (8)
C2	0.0327 (10)	0.0302 (10)	0.0288 (10)	0.0028 (7)	0.0048 (8)	0.0083 (8)
C12	0.0312 (10)	0.0360 (10)	0.0221 (9)	0.0096 (8)	−0.0027 (7)	−0.0014 (8)
C14	0.0240 (9)	0.0331 (10)	0.0405 (11)	−0.0029 (7)	0.0030 (8)	−0.0014 (8)
C13	0.0219 (9)	0.0430 (11)	0.0379 (11)	0.0040 (8)	0.0075 (8)	−0.0015 (9)
C15	0.0483 (13)	0.0416 (12)	0.0352 (11)	0.0223 (10)	−0.0008 (9)	−0.0042 (9)

S1—O2	1.4224 (15)	C6—C7	1.381 (3)
S1—O1	1.4278 (15)	C6—H6	0.9500
S1—N1	1.6654 (15)	C7—H7	0.9500
S1—C9	1.7496 (18)	C3—C2	1.438 (3)
Cl1—C5	1.7487 (19)	C11—C10	1.383 (3)
C9—C14	1.382 (2)	C11—C12	1.387 (3)
C9—C10	1.384 (3)	C11—H11	0.9500
N1—C8	1.407 (2)	C10—H10	0.9500
N1—C1	1.408 (2)	C2—H2	0.9500
C1—C2	1.345 (3)	C12—C13	1.387 (3)
C1—H1	0.9500	C12—C15	1.501 (3)
C5—C4	1.371 (3)	C14—C13	1.382 (3)
C5—C6	1.392 (3)	C14—H14	0.9500
C4—C3	1.396 (3)	C13—H13	0.9500
C4—H4	0.9500	C15—H15A	0.9800
C8—C7	1.386 (2)	C15—H16B	0.9800
C8—C3	1.406 (2)	C15—H17C	0.9800
O2—S1—O1	120.84 (9)	C8—C7—H7	121.3
O2—S1—N1	104.64 (8)	C4—C3—C8	119.13 (17)
O1—S1—N1	105.94 (8)	C4—C3—C2	133.19 (17)
O2—S1—C9	110.18 (9)	C8—C3—C2	107.68 (16)
O1—S1—C9	108.90 (9)	C10—C11—C12	121.37 (18)
N1—S1—C9	105.07 (8)	C10—C11—H11	119.3
C14—C9—C10	121.13 (17)	C12—C11—H11	119.3
C14—C9—S1	118.77 (14)	C11—C10—C9	118.83 (17)
C10—C9—S1	120.05 (13)	C11—C10—H10	120.6
C8—N1—C1	107.88 (14)	C9—C10—H10	120.6
C8—N1—S1	125.11 (12)	C1—C2—C3	107.74 (16)
C1—N1—S1	122.18 (13)	C1—C2—H2	126.1
C2—C1—N1	109.77 (17)	C3—C2—H2	126.1
C2—C1—H1	125.1	C13—C12—C11	118.36 (17)
N1—C1—H1	125.1	C13—C12—C15	120.65 (18)
C4—C5—C6	122.48 (18)	C11—C12—C15	120.98 (19)
C4—C5—Cl1	119.19 (15)	C9—C14—C13	118.91 (18)
C6—C5—Cl1	118.33 (15)	C9—C14—H14	120.5
C5—C4—C3	118.06 (17)	C13—C14—H14	120.5
C5—C4—H4	121.0	C14—C13—C12	121.40 (17)
C3—C4—H4	121.0	C14—C13—H13	119.3
C7—C8—C3	122.42 (17)	C12—C13—H13	119.3
C7—C8—N1	130.71 (16)	C12—C15—H15A	109.5
C3—C8—N1	106.86 (15)	C12—C15—H16B	109.5
C7—C6—C5	120.51 (18)	H15A—C15—H16B	109.5
C7—C6—H6	119.7	C12—C15—H17C	109.5
C5—C6—H6	119.7	H15A—C15—H17C	109.5
C6—C7—C8	117.39 (17)	H16B—C15—H17C	109.5
C6—C7—H7	121.3
O2—S1—C9—C14	27.82 (18)	C5—C6—C7—C8	−1.0 (3)
O1—S1—C9—C14	162.50 (15)	C3—C8—C7—C6	0.9 (3)
N1—S1—C9—C14	−84.38 (16)	N1—C8—C7—C6	−178.52 (16)
O2—S1—C9—C10	−154.75 (15)	C5—C4—C3—C8	0.1 (2)
O1—S1—C9—C10	−20.06 (17)	C5—C4—C3—C2	−179.33 (18)
N1—S1—C9—C10	93.06 (16)	C7—C8—C3—C4	−0.5 (3)
O2—S1—N1—C8	172.54 (14)	N1—C8—C3—C4	179.06 (15)
O1—S1—N1—C8	43.81 (16)	C7—C8—C3—C2	179.10 (16)
C9—S1—N1—C8	−71.38 (15)	N1—C8—C3—C2	−1.36 (18)
O2—S1—N1—C1	−35.12 (16)	C12—C11—C10—C9	0.0 (3)
O1—S1—N1—C1	−163.85 (14)	C14—C9—C10—C11	−0.2 (3)
C9—S1—N1—C1	80.95 (15)	S1—C9—C10—C11	−177.58 (14)
C8—N1—C1—C2	−2.7 (2)	N1—C1—C2—C3	1.8 (2)
S1—N1—C1—C2	−159.19 (13)	C4—C3—C2—C1	179.22 (19)
C6—C5—C4—C3	−0.2 (3)	C8—C3—C2—C1	−0.3 (2)
Cl1—C5—C4—C3	179.67 (13)	C10—C11—C12—C13	0.1 (3)
C1—N1—C8—C7	−178.07 (17)	C10—C11—C12—C15	−179.14 (18)
S1—N1—C8—C7	−22.5 (3)	C10—C9—C14—C13	0.3 (3)
C1—N1—C8—C3	2.45 (18)	S1—C9—C14—C13	177.70 (15)
S1—N1—C8—C3	158.06 (12)	C9—C14—C13—C12	−0.2 (3)
C4—C5—C6—C7	0.7 (3)	C11—C12—C13—C14	0.0 (3)
Cl1—C5—C6—C7	−179.22 (14)	C15—C12—C13—C14	179.24 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.95	2.54	3.327 (2)	140
C4—H4···O1ii	0.95	2.49	3.192 (2)	131
C14—H14···O1iii	0.95	2.59	3.333 (2)	135
C7—H7···O1	0.95	2.44	3.025 (2)	120
C10—H10···O1	0.95	2.59	2.943 (2)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.95	2.54	3.327 (2)	140
C4—H4⋯O1ii	0.95	2.49	3.192 (2)	131
C14—H14⋯O1iii	0.95	2.59	3.333 (2)	135

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