cis-3-(p-Bromo­styryl)-2-methyl-N-(phenyl­sulfonyl)­indole

In the title compound, C₂₃H₁₈BrNO₂S, the bromo­phenyl group is oriented cis with respect to the indole moiety. The phenyl­sulfonyl group is nearly perpendicular to the indole ring system, forming a dihedral angle of 84.6 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.112
• Data-to-parameter ratio = 17.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.865
          Tmax scaled      0.395 Tmin scaled      0.360

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

cis-3-(p-bromostyryl)-2-methyl-N-(phenylsulfonyl)indole

Crystal data

C23H18BrNO2S	Z = 2
Mr = 452.35	F(000) = 460
Triclinic, P1	Dx = 1.524 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2443 (3) Å	Cell parameters from 3502 reflections
b = 10.4161 (3) Å	θ = 2.0–27.5°
c = 11.4190 (3) Å	µ = 2.21 mm^−1
α = 65.064 (1)°	T = 293 K
β = 89.772 (1)°	Block, colourless
γ = 65.707 (1)°	0.48 × 0.46 × 0.42 mm
V = 985.65 (5) Å^3

Data collection

Siemens SMART CCD area-detector diffractometer	4420 independent reflections
Radiation source: fine-focus sealed tube	3451 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.417, Tmax = 0.457	k = −13→12
6560 measured reflections	l = −14→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.112
S = 1.03	(Δ/σ)max = 0.001
4420 reflections	Δρmax = 0.66 e Å^−3
255 parameters	Δρmin = −0.68 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.34050 (3)	0.59082 (4)	0.09226 (3)	0.06734 (15)
S1	0.13483 (7)	−0.00321 (7)	0.74939 (6)	0.04784 (17)
N1	0.2465 (2)	0.0439 (2)	0.81058 (19)	0.0443 (4)
O1	0.0079 (2)	0.0352 (3)	0.8047 (2)	0.0684 (6)
O2	0.2179 (2)	−0.1602 (2)	0.7675 (2)	0.0649 (5)
C2	0.0877 (3)	0.1885 (3)	0.9311 (2)	0.0519 (6)
H2	0.0121	0.1621	0.9268	0.062*
C2A	0.2059 (2)	0.1425 (3)	0.8732 (2)	0.0412 (5)
C3	0.0861 (3)	0.2755 (4)	0.9958 (3)	0.0583 (7)
H3	0.0084	0.3066	1.0364	0.070*
C4	0.1973 (3)	0.3174 (3)	1.0017 (3)	0.0595 (7)
H4	0.1932	0.3756	1.0461	0.071*
C5	0.3141 (3)	0.2732 (3)	0.9421 (2)	0.0506 (6)
H5	0.3887	0.3011	0.9461	0.061*
C5A	0.3182 (2)	0.1863 (3)	0.8759 (2)	0.0414 (5)
C6	0.4248 (2)	0.1187 (3)	0.8094 (2)	0.0434 (5)
C7	0.3813 (3)	0.0323 (3)	0.7719 (2)	0.0458 (5)
C8	0.4618 (3)	−0.0689 (4)	0.7091 (3)	0.0647 (7)
H8A	0.4117	−0.0209	0.6196	0.097*
H8B	0.4664	−0.1722	0.7571	0.097*
H8C	0.5592	−0.0787	0.7102	0.097*
C9	0.0868 (2)	0.1279 (3)	0.5798 (2)	0.0429 (5)
C10	−0.0010 (3)	0.2886 (3)	0.5364 (3)	0.0553 (6)
H10	−0.0332	0.3278	0.5962	0.066*
C11	−0.0398 (3)	0.3894 (4)	0.4022 (3)	0.0687 (8)
H11	−0.0989	0.4975	0.3715	0.082*
C12	0.0080 (4)	0.3316 (4)	0.3139 (3)	0.0734 (9)
H12	−0.0191	0.4008	0.2239	0.088*
C13	0.0956 (4)	0.1727 (4)	0.3572 (3)	0.0719 (8)
H13	0.1284	0.1344	0.2970	0.086*
C14	0.1348 (3)	0.0697 (4)	0.4909 (3)	0.0583 (7)
H14	0.1932	−0.0384	0.5208	0.070*
C15	0.5623 (3)	0.1320 (3)	0.7964 (3)	0.0505 (6)
H15	0.6262	0.0884	0.8755	0.061*
C16	0.6085 (2)	0.1973 (3)	0.6881 (3)	0.0485 (6)
H16	0.7029	0.1850	0.7042	0.058*
C17	0.5382 (2)	0.2851 (3)	0.5478 (2)	0.0418 (5)
C18	0.6196 (2)	0.3347 (3)	0.4560 (3)	0.0488 (6)
H18	0.7162	0.3065	0.4866	0.059*
C19	0.5635 (3)	0.4233 (3)	0.3224 (3)	0.0525 (6)
H19	0.6212	0.4537	0.2642	0.063*
C20	0.4205 (3)	0.4661 (3)	0.2763 (2)	0.0459 (5)
C21	0.3351 (3)	0.4207 (3)	0.3623 (3)	0.0520 (6)
H21	0.2384	0.4507	0.3305	0.062*
C22	0.3936 (3)	0.3305 (3)	0.4964 (3)	0.0511 (6)
H22	0.3354	0.2993	0.5536	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0759 (2)	0.0780 (2)	0.04626 (18)	−0.04233 (18)	0.01067 (14)	−0.01971 (15)
S1	0.0575 (4)	0.0525 (4)	0.0383 (3)	−0.0361 (3)	0.0050 (3)	−0.0140 (3)
N1	0.0460 (10)	0.0496 (11)	0.0389 (10)	−0.0254 (9)	0.0039 (8)	−0.0181 (9)
O1	0.0706 (12)	0.1043 (16)	0.0592 (12)	−0.0638 (12)	0.0245 (10)	−0.0389 (12)
O2	0.0876 (14)	0.0460 (10)	0.0550 (11)	−0.0373 (10)	−0.0023 (10)	−0.0112 (9)
C2	0.0520 (14)	0.0610 (15)	0.0386 (12)	−0.0272 (12)	0.0075 (10)	−0.0177 (11)
C2A	0.0447 (12)	0.0421 (11)	0.0272 (10)	−0.0201 (10)	−0.0014 (8)	−0.0073 (8)
C3	0.0587 (15)	0.0649 (17)	0.0454 (14)	−0.0229 (13)	0.0105 (12)	−0.0253 (13)
C4	0.0744 (18)	0.0552 (15)	0.0453 (14)	−0.0267 (14)	0.0036 (13)	−0.0225 (12)
C5	0.0616 (15)	0.0440 (13)	0.0391 (12)	−0.0275 (12)	−0.0019 (11)	−0.0096 (10)
C5A	0.0451 (12)	0.0371 (11)	0.0296 (10)	−0.0192 (9)	−0.0024 (8)	−0.0040 (8)
C6	0.0405 (11)	0.0416 (12)	0.0356 (11)	−0.0185 (10)	−0.0020 (9)	−0.0070 (9)
C7	0.0414 (12)	0.0477 (13)	0.0411 (12)	−0.0200 (10)	0.0025 (9)	−0.0145 (10)
C8	0.0559 (16)	0.0723 (19)	0.075 (2)	−0.0268 (14)	0.0134 (14)	−0.0436 (17)
C9	0.0434 (11)	0.0468 (12)	0.0392 (11)	−0.0261 (10)	0.0017 (9)	−0.0146 (10)
C10	0.0502 (14)	0.0514 (14)	0.0586 (16)	−0.0213 (12)	0.0031 (12)	−0.0221 (12)
C11	0.0612 (17)	0.0462 (15)	0.070 (2)	−0.0200 (13)	−0.0078 (14)	−0.0061 (14)
C12	0.076 (2)	0.080 (2)	0.0448 (15)	−0.0424 (18)	−0.0060 (14)	−0.0051 (15)
C13	0.081 (2)	0.087 (2)	0.0453 (15)	−0.0381 (19)	0.0076 (14)	−0.0274 (16)
C14	0.0636 (16)	0.0569 (15)	0.0481 (14)	−0.0221 (13)	0.0023 (12)	−0.0236 (12)
C15	0.0411 (12)	0.0513 (14)	0.0464 (13)	−0.0219 (11)	−0.0036 (10)	−0.0105 (11)
C16	0.0325 (11)	0.0461 (13)	0.0563 (15)	−0.0172 (10)	0.0010 (10)	−0.0151 (11)
C17	0.0350 (11)	0.0371 (11)	0.0493 (13)	−0.0157 (9)	0.0083 (9)	−0.0171 (10)
C18	0.0353 (11)	0.0432 (12)	0.0644 (16)	−0.0207 (10)	0.0112 (10)	−0.0189 (12)
C19	0.0472 (13)	0.0516 (14)	0.0592 (15)	−0.0280 (11)	0.0200 (11)	−0.0205 (12)
C20	0.0502 (13)	0.0430 (12)	0.0447 (12)	−0.0231 (11)	0.0100 (10)	−0.0183 (10)
C21	0.0392 (12)	0.0596 (15)	0.0506 (14)	−0.0232 (11)	0.0069 (10)	−0.0189 (12)
C22	0.0370 (12)	0.0611 (15)	0.0476 (13)	−0.0241 (11)	0.0116 (10)	−0.0168 (12)

Geometric parameters (Å, º)

Br1—C20	1.900 (3)	C9—C10	1.387 (4)
S1—O2	1.419 (2)	C10—C11	1.383 (4)
S1—O1	1.424 (2)	C10—H10	0.93
S1—N1	1.673 (2)	C11—C12	1.373 (5)
S1—C9	1.756 (2)	C11—H11	0.93
N1—C2A	1.415 (3)	C12—C13	1.372 (5)
N1—C7	1.421 (3)	C12—H12	0.93
C2—C2A	1.385 (4)	C13—C14	1.382 (4)
C2—C3	1.384 (4)	C13—H13	0.93
C2—H2	0.93	C14—H14	0.93
C2A—C5A	1.406 (3)	C15—C16	1.330 (4)
C3—C4	1.388 (4)	C15—H15	0.93
C3—H3	0.93	C16—C17	1.467 (3)
C4—C5	1.383 (4)	C16—H16	0.93
C4—H4	0.93	C17—C18	1.397 (3)
C5—C5A	1.393 (3)	C17—C22	1.400 (3)
C5—H5	0.93	C18—C19	1.376 (4)
C5A—C6	1.440 (3)	C18—H18	0.93
C6—C7	1.360 (3)	C19—C20	1.375 (4)
C6—C15	1.472 (3)	C19—H19	0.93
C7—C8	1.491 (4)	C20—C21	1.377 (4)
C8—H8A	0.96	C21—C22	1.384 (4)
C8—H8B	0.96	C21—H21	0.93
C8—H8C	0.96	C22—H22	0.93
C9—C14	1.382 (4)
O2—S1—O1	120.2 (1)	C10—C9—S1	119.5 (2)
O2—S1—N1	107.61 (11)	C11—C10—C9	118.6 (3)
O1—S1—N1	106.47 (11)	C11—C10—H10	120.7
O2—S1—C9	108.61 (12)	C9—C10—H10	120.7
O1—S1—C9	108.75 (12)	C12—C11—C10	120.7 (3)
N1—S1—C9	104.0 (1)	C12—C11—H11	119.6
C2A—N1—C7	108.4 (2)	C10—C11—H11	119.6
C2A—N1—S1	125.6 (2)	C13—C12—C11	120.5 (3)
C7—N1—S1	123.4 (2)	C13—C12—H12	119.7
C2A—C2—C3	117.5 (2)	C11—C12—H12	119.7
C2A—C2—H2	121.2	C12—C13—C14	119.7 (3)
C3—C2—H2	121.2	C12—C13—H13	120.2
C2—C2A—C5A	121.6 (2)	C14—C13—H13	120.2
C2—C2A—N1	131.7 (2)	C13—C14—C9	119.8 (3)
C5A—C2A—N1	106.7 (2)	C13—C14—H14	120.1
C2—C3—C4	121.8 (3)	C9—C14—H14	120.1
C2—C3—H3	119.1	C16—C15—C6	129.4 (2)
C4—C3—H3	119.1	C16—C15—H15	115.3
C5—C4—C3	120.5 (3)	C6—C15—H15	115.3
C5—C4—H4	119.7	C15—C16—C17	131.9 (2)
C3—C4—H4	119.7	C15—C16—H16	114.0
C4—C5—C5A	118.9 (2)	C17—C16—H16	114.0
C4—C5—H5	120.6	C18—C17—C22	116.1 (2)
C5A—C5—H5	120.6	C18—C17—C16	117.8 (2)
C5—C5A—C2A	119.6 (2)	C22—C17—C16	126.0 (2)
C5—C5A—C6	132.2 (2)	C19—C18—C17	123.0 (2)
C2A—C5A—C6	108.0 (2)	C19—C18—H18	118.5
C7—C6—C5A	108.2 (2)	C17—C18—H18	118.5
C7—C6—C15	127.1 (2)	C18—C19—C20	118.9 (2)
C5A—C6—C15	124.6 (2)	C18—C19—H19	120.6
C6—C7—N1	108.7 (2)	C20—C19—H19	120.6
C6—C7—C8	127.7 (2)	C19—C20—C21	120.5 (2)
N1—C7—C8	123.6 (2)	C19—C20—Br1	119.42 (19)
C7—C8—H8A	109.5	C21—C20—Br1	120.04 (19)
C7—C8—H8B	109.5	C20—C21—C22	119.9 (2)
H8A—C8—H8B	109.5	C20—C21—H21	120.1
C7—C8—H8C	109.5	C22—C21—H21	120.1
H8A—C8—H8C	109.5	C21—C22—C17	121.5 (2)
H8B—C8—H8C	109.5	C21—C22—H22	119.2
C14—C9—C10	120.7 (2)	C17—C22—H22	119.2
C14—C9—S1	119.8 (2)
O2—S1—N1—C2A	−146.25 (19)	C2A—N1—C7—C8	176.7 (2)
O1—S1—N1—C2A	−16.1 (2)	S1—N1—C7—C8	−20.6 (3)
C9—S1—N1—C2A	98.6 (2)	O2—S1—C9—C14	−1.9 (2)
O2—S1—N1—C7	54.1 (2)	O1—S1—C9—C14	−134.3 (2)
O1—S1—N1—C7	−175.8 (2)	N1—S1—C9—C14	112.5 (2)
C9—S1—N1—C7	−61.0 (2)	O2—S1—C9—C10	177.02 (19)
C3—C2—C2A—C5A	−2.0 (4)	O1—S1—C9—C10	44.6 (2)
C3—C2—C2A—N1	174.1 (2)	N1—S1—C9—C10	−68.6 (2)
C7—N1—C2A—C2	−178.2 (2)	C14—C9—C10—C11	0.1 (4)
S1—N1—C2A—C2	19.6 (4)	S1—C9—C10—C11	−178.8 (2)
C7—N1—C2A—C5A	−1.7 (2)	C9—C10—C11—C12	−0.2 (4)
S1—N1—C2A—C5A	−163.96 (16)	C10—C11—C12—C13	−0.1 (5)
C2A—C2—C3—C4	0.8 (4)	C11—C12—C13—C14	0.6 (5)
C2—C3—C4—C5	0.2 (4)	C12—C13—C14—C9	−0.7 (5)
C3—C4—C5—C5A	0.1 (4)	C10—C9—C14—C13	0.4 (4)
C4—C5—C5A—C2A	−1.3 (3)	S1—C9—C14—C13	179.3 (2)
C4—C5—C5A—C6	−177.4 (2)	C7—C6—C15—C16	66.3 (4)
C2—C2A—C5A—C5	2.3 (3)	C5A—C6—C15—C16	−119.4 (3)
N1—C2A—C5A—C5	−174.6 (2)	C6—C15—C16—C17	4.2 (5)
C2—C2A—C5A—C6	179.2 (2)	C15—C16—C17—C18	−177.9 (3)
N1—C2A—C5A—C6	2.3 (2)	C15—C16—C17—C22	4.9 (5)
C5—C5A—C6—C7	174.3 (2)	C22—C17—C18—C19	0.1 (4)
C2A—C5A—C6—C7	−2.1 (3)	C16—C17—C18—C19	−177.3 (2)
C5—C5A—C6—C15	−0.9 (4)	C17—C18—C19—C20	0.3 (4)
C2A—C5A—C6—C15	−177.3 (2)	C18—C19—C20—C21	−0.2 (4)
C5A—C6—C7—N1	1.0 (3)	C18—C19—C20—Br1	179.18 (19)
C15—C6—C7—N1	176.0 (2)	C19—C20—C21—C22	−0.4 (4)
C5A—C6—C7—C8	−175.1 (3)	Br1—C20—C21—C22	−179.7 (2)
C15—C6—C7—C8	0.0 (4)	C20—C21—C22—C17	0.8 (4)
C2A—N1—C7—C6	0.5 (3)	C18—C17—C22—C21	−0.7 (4)
S1—N1—C7—C6	163.16 (17)	C16—C17—C22—C21	176.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.30	2.886 (5)	121
C8—H8B···O2	0.96	2.50	3.000 (5)	112
C14—H14···O2	0.93	2.52	2.898 (3)	105