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)°.
Supporting information
CCDC reference: 165825
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | |
Data collection top
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 top
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)] = 0.039 | H-atom parameters constrained |
wR(F2) = 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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.015 (3) |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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 |