The phenyl ring in the title compound, C
15H
11Br
2NO
2S, makes a dihedral angle of 81.8 (1)° with the mean plane of the indole system. The molecular structure is stabilized by C—H
O hydrogen bonds.
Supporting information
CCDC reference: 640286
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.030
- wR factor = 0.077
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.98 Deg.
Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.89 Sigma
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.85
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4
PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O1 .. 3.18 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. Br2 .. 3.57 Ang.
Alert level G
ABSTM02_ALERT_3_G 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 0.849
Tmax scaled 0.372 Tmin scaled 0.231
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
3-Bromo-2-bromomethyl-1-phenylsulfonyl-1
H-indole
top
Crystal data top
C15H11Br2NO2S | Z = 2 |
Mr = 429.12 | F(000) = 420 |
Triclinic, P1 | Dx = 1.883 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5730 (1) Å | Cell parameters from 25 reflections |
b = 9.5220 (1) Å | θ = 2.2–25.0° |
c = 10.9660 (2) Å | µ = 5.50 mm−1 |
α = 102.048 (2)° | T = 293 K |
β = 90.763 (1)° | Prism, colourless |
γ = 101.462 (2)° | 0.32 × 0.23 × 0.18 mm |
V = 756.68 (2) Å3 | |
Data collection top
MACH3 single-crystal diffractometer | 1920 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 25.0°, θmin = 2.2° |
ω–2θ scans | h = −1→8 |
Absorption correction: ψ scan (North et al., 1968) | k = −11→11 |
Tmin = 0.272, Tmax = 0.438 | l = −13→13 |
3303 measured reflections | 1 standard reflections every 100 reflections |
2645 independent reflections | intensity decay: 2% |
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)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0379P)2 + 0.431P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
2645 reflections | Δρmax = 0.48 e Å−3 |
191 parameters | Δρmin = −0.45 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: 0.0026 (9) |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | 0.35276 (6) | 0.31835 (4) | 0.39733 (4) | 0.0514 (2) | |
Br2 | 0.23060 (6) | 0.03929 (6) | 0.05669 (4) | 0.0688 (2) | |
S1 | 0.30122 (12) | −0.29130 (10) | 0.24780 (9) | 0.0405 (3) | |
O1 | 0.3639 (4) | −0.3726 (3) | 0.3278 (3) | 0.0524 (10) | |
O2 | 0.3914 (4) | −0.2711 (3) | 0.1384 (3) | 0.0536 (10) | |
N1 | 0.3079 (4) | −0.1229 (3) | 0.3349 (3) | 0.0337 (9) | |
C1 | 0.4225 (5) | 0.0404 (4) | 0.1808 (3) | 0.0438 (12) | |
C2 | 0.3502 (4) | 0.0142 (4) | 0.2991 (3) | 0.0332 (11) | |
C3 | 0.3198 (4) | 0.1177 (4) | 0.3972 (3) | 0.0331 (11) | |
C4 | 0.2111 (5) | 0.1104 (4) | 0.6182 (3) | 0.0405 (12) | |
C5 | 0.1544 (5) | 0.0149 (5) | 0.6944 (3) | 0.0456 (14) | |
C6 | 0.1456 (5) | −0.1349 (5) | 0.6533 (4) | 0.0464 (14) | |
C7 | 0.1944 (5) | −0.1940 (4) | 0.5365 (3) | 0.0410 (12) | |
C8 | 0.2505 (4) | −0.0976 (4) | 0.4586 (3) | 0.0308 (10) | |
C9 | 0.2587 (4) | 0.0536 (4) | 0.4982 (3) | 0.0314 (10) | |
C10 | 0.0710 (5) | −0.3666 (4) | 0.2072 (4) | 0.0402 (11) | |
C11 | −0.0224 (6) | −0.4645 (4) | 0.2718 (4) | 0.0546 (16) | |
C12 | −0.2031 (6) | −0.5236 (5) | 0.2386 (5) | 0.0663 (19) | |
C13 | −0.2868 (6) | −0.4865 (5) | 0.1424 (5) | 0.0638 (19) | |
C14 | −0.1929 (6) | −0.3913 (5) | 0.0782 (5) | 0.0633 (17) | |
C15 | −0.0129 (6) | −0.3298 (4) | 0.1084 (4) | 0.0505 (14) | |
H1A | 0.48890 | −0.03490 | 0.14710 | 0.0520* | |
H1B | 0.50610 | 0.13450 | 0.19610 | 0.0520* | |
H4 | 0.21770 | 0.21060 | 0.64580 | 0.0480* | |
H5 | 0.12140 | 0.05080 | 0.77450 | 0.0550* | |
H6 | 0.10540 | −0.19710 | 0.70670 | 0.0560* | |
H7 | 0.19010 | −0.29420 | 0.51070 | 0.0490* | |
H11 | 0.03500 | −0.49040 | 0.33670 | 0.0650* | |
H12 | −0.26790 | −0.58910 | 0.28200 | 0.0800* | |
H13 | −0.40830 | −0.52640 | 0.12090 | 0.0760* | |
H14 | −0.25120 | −0.36720 | 0.01260 | 0.0760* | |
H15 | 0.05080 | −0.26520 | 0.06370 | 0.0610* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0549 (3) | 0.0318 (2) | 0.0680 (3) | 0.0053 (2) | 0.0051 (2) | 0.0153 (2) |
Br2 | 0.0598 (3) | 0.1072 (4) | 0.0467 (3) | 0.0144 (3) | 0.0001 (2) | 0.0357 (3) |
S1 | 0.0346 (5) | 0.0350 (5) | 0.0486 (6) | 0.0112 (4) | 0.0010 (4) | −0.0023 (4) |
O1 | 0.0466 (16) | 0.0384 (14) | 0.074 (2) | 0.0186 (13) | −0.0054 (14) | 0.0074 (14) |
O2 | 0.0466 (17) | 0.0570 (18) | 0.0510 (17) | 0.0129 (14) | 0.0146 (13) | −0.0051 (14) |
N1 | 0.0355 (16) | 0.0286 (15) | 0.0351 (16) | 0.0062 (13) | 0.0028 (13) | 0.0032 (13) |
C1 | 0.036 (2) | 0.056 (2) | 0.041 (2) | 0.0068 (18) | 0.0049 (17) | 0.0164 (19) |
C2 | 0.0263 (18) | 0.039 (2) | 0.0336 (19) | 0.0042 (15) | −0.0004 (15) | 0.0088 (17) |
C3 | 0.0301 (18) | 0.0261 (17) | 0.041 (2) | 0.0018 (14) | −0.0018 (16) | 0.0063 (16) |
C4 | 0.041 (2) | 0.039 (2) | 0.039 (2) | 0.0105 (17) | −0.0003 (17) | 0.0005 (17) |
C5 | 0.044 (2) | 0.062 (3) | 0.031 (2) | 0.014 (2) | 0.0049 (17) | 0.0075 (19) |
C6 | 0.043 (2) | 0.060 (3) | 0.041 (2) | 0.008 (2) | 0.0050 (18) | 0.024 (2) |
C7 | 0.044 (2) | 0.035 (2) | 0.045 (2) | 0.0069 (17) | 0.0020 (18) | 0.0123 (17) |
C8 | 0.0256 (17) | 0.0334 (18) | 0.0318 (19) | 0.0051 (15) | −0.0017 (14) | 0.0049 (15) |
C9 | 0.0253 (17) | 0.0309 (18) | 0.0363 (19) | 0.0023 (14) | −0.0018 (15) | 0.0073 (15) |
C10 | 0.038 (2) | 0.0315 (19) | 0.046 (2) | 0.0115 (17) | −0.0005 (18) | −0.0070 (17) |
C11 | 0.048 (3) | 0.044 (2) | 0.067 (3) | 0.004 (2) | −0.005 (2) | 0.007 (2) |
C12 | 0.047 (3) | 0.050 (3) | 0.096 (4) | 0.001 (2) | 0.004 (3) | 0.011 (3) |
C13 | 0.040 (3) | 0.048 (3) | 0.091 (4) | 0.007 (2) | −0.009 (2) | −0.010 (3) |
C14 | 0.057 (3) | 0.053 (3) | 0.072 (3) | 0.014 (2) | −0.024 (2) | −0.005 (2) |
C15 | 0.051 (3) | 0.045 (2) | 0.051 (2) | 0.012 (2) | −0.004 (2) | −0.0016 (19) |
Geometric parameters (Å, º) top
Br1—C3 | 1.877 (4) | C10—C11 | 1.378 (6) |
Br2—C1 | 1.975 (4) | C10—C15 | 1.389 (6) |
S1—O1 | 1.419 (3) | C11—C12 | 1.385 (7) |
S1—O2 | 1.417 (3) | C12—C13 | 1.366 (7) |
S1—N1 | 1.677 (3) | C13—C14 | 1.359 (7) |
S1—C10 | 1.761 (4) | C14—C15 | 1.379 (7) |
N1—C2 | 1.418 (5) | C1—H1A | 0.9701 |
N1—C8 | 1.417 (5) | C1—H1B | 0.9699 |
C1—C2 | 1.464 (5) | C4—H4 | 0.9298 |
C2—C3 | 1.355 (5) | C5—H5 | 0.9302 |
C3—C9 | 1.413 (5) | C6—H6 | 0.9296 |
C4—C5 | 1.372 (6) | C7—H7 | 0.9307 |
C4—C9 | 1.395 (5) | C11—H11 | 0.9295 |
C5—C6 | 1.391 (7) | C12—H12 | 0.9299 |
C6—C7 | 1.374 (5) | C13—H13 | 0.9298 |
C7—C8 | 1.391 (5) | C14—H14 | 0.9305 |
C8—C9 | 1.403 (5) | C15—H15 | 0.9304 |
| | | |
Br1···O1i | 3.176 (3) | C6···H1Bii | 3.0923 |
Br1···O1ii | 3.563 (3) | C11···H7 | 3.0265 |
Br2···Br2iii | 3.5724 (7) | C11···H4ix | 3.0649 |
Br1···H4 | 3.2167 | C12···H4ix | 3.0099 |
Br1···H12iv | 3.1913 | C12···H6x | 3.0686 |
Br1···H1B | 2.9234 | C13···H4ix | 3.0731 |
Br2···H5v | 3.2220 | C15···H5ix | 2.9755 |
Br2···H15 | 2.9653 | H1A···S1 | 2.9981 |
Br2···H1Avi | 3.1034 | H1A···O2 | 2.2048 |
S1···H1A | 2.9981 | H1A···Br2vi | 3.1034 |
S1···H7 | 3.0181 | H1B···Br1 | 2.9234 |
O1···Br1vii | 3.176 (3) | H1B···C6ii | 3.0923 |
O1···C7 | 3.016 (5) | H4···Br1 | 3.2167 |
O1···Br1ii | 3.563 (3) | H4···C11ix | 3.0649 |
O2···C1 | 2.866 (5) | H4···C12ix | 3.0099 |
O2···C13viii | 3.417 (6) | H4···C13ix | 3.0731 |
O1···H11 | 2.5325 | H5···Br2xi | 3.2220 |
O1···H7 | 2.4795 | H5···C15ix | 2.9755 |
O2···H1A | 2.2048 | H6···C12x | 3.0686 |
O2···H15 | 2.7107 | H7···S1 | 3.0181 |
C1···O2 | 2.866 (5) | H7···O1 | 2.4795 |
C1···C6ii | 3.579 (5) | H7···C11 | 3.0265 |
C4···C8ix | 3.557 (5) | H7···H11 | 2.4679 |
C6···C1ii | 3.579 (5) | H11···O1 | 2.5325 |
C7···O1 | 3.016 (5) | H11···H7 | 2.4679 |
C7···C11 | 3.581 (5) | H12···Br1xii | 3.1913 |
C8···C4ix | 3.557 (5) | H15···Br2 | 2.9653 |
C11···C7 | 3.581 (5) | H15···O2 | 2.7107 |
C13···O2viii | 3.417 (6) | | |
| | | |
O1—S1—O2 | 120.48 (19) | C10—C11—C12 | 119.0 (4) |
O1—S1—N1 | 106.32 (17) | C11—C12—C13 | 120.4 (4) |
O1—S1—C10 | 108.22 (19) | C12—C13—C14 | 120.1 (4) |
O2—S1—N1 | 106.30 (17) | C13—C14—C15 | 121.2 (5) |
O2—S1—C10 | 109.1 (2) | C10—C15—C14 | 118.4 (4) |
N1—S1—C10 | 105.43 (17) | Br2—C1—H1A | 109.16 |
S1—N1—C2 | 128.7 (3) | Br2—C1—H1B | 109.14 |
S1—N1—C8 | 123.1 (2) | C2—C1—H1A | 109.12 |
C2—N1—C8 | 107.9 (3) | C2—C1—H1B | 109.20 |
Br2—C1—C2 | 112.2 (3) | H1A—C1—H1B | 107.90 |
N1—C2—C1 | 126.5 (3) | C5—C4—H4 | 120.83 |
N1—C2—C3 | 107.2 (3) | C9—C4—H4 | 120.76 |
C1—C2—C3 | 126.2 (3) | C4—C5—H5 | 119.56 |
Br1—C3—C2 | 124.3 (3) | C6—C5—H5 | 119.65 |
Br1—C3—C9 | 125.0 (3) | C5—C6—H6 | 118.87 |
C2—C3—C9 | 110.8 (3) | C7—C6—H6 | 118.90 |
C5—C4—C9 | 118.4 (3) | C6—C7—H7 | 121.40 |
C4—C5—C6 | 120.8 (3) | C8—C7—H7 | 121.49 |
C5—C6—C7 | 122.2 (4) | C10—C11—H11 | 120.50 |
C6—C7—C8 | 117.1 (4) | C12—C11—H11 | 120.53 |
N1—C8—C7 | 131.0 (3) | C11—C12—H12 | 119.78 |
N1—C8—C9 | 107.6 (3) | C13—C12—H12 | 119.77 |
C7—C8—C9 | 121.4 (3) | C12—C13—H13 | 119.91 |
C3—C9—C4 | 133.5 (4) | C14—C13—H13 | 119.96 |
C3—C9—C8 | 106.5 (3) | C13—C14—H14 | 119.37 |
C4—C9—C8 | 120.1 (3) | C15—C14—H14 | 119.38 |
S1—C10—C11 | 119.5 (3) | C10—C15—H15 | 120.82 |
S1—C10—C15 | 119.7 (3) | C14—C15—H15 | 120.81 |
C11—C10—C15 | 120.8 (4) | | |
| | | |
O1—S1—N1—C2 | 144.5 (3) | C1—C2—C3—Br1 | 3.7 (5) |
O1—S1—N1—C8 | −42.7 (3) | C2—C3—C9—C8 | −0.4 (4) |
O2—S1—N1—C2 | 15.0 (4) | Br1—C3—C9—C8 | 179.1 (2) |
O2—S1—N1—C8 | −172.2 (3) | C2—C3—C9—C4 | 179.3 (4) |
C10—S1—N1—C2 | −100.8 (3) | Br1—C3—C9—C4 | −1.2 (5) |
C10—S1—N1—C8 | 72.1 (3) | C9—C4—C5—C6 | 0.4 (6) |
N1—S1—C10—C11 | −100.7 (3) | C5—C4—C9—C8 | −0.9 (5) |
O1—S1—C10—C15 | −165.5 (3) | C5—C4—C9—C3 | 179.4 (4) |
O2—S1—C10—C15 | −32.7 (4) | C4—C5—C6—C7 | 0.7 (6) |
N1—S1—C10—C15 | 81.1 (4) | C5—C6—C7—C8 | −1.2 (6) |
O1—S1—C10—C11 | 12.8 (4) | C6—C7—C8—C9 | 0.7 (5) |
O2—S1—C10—C11 | 145.5 (3) | C6—C7—C8—N1 | −179.7 (4) |
S1—N1—C8—C7 | 5.9 (5) | C7—C8—C9—C4 | 0.4 (5) |
S1—N1—C2—C3 | 173.8 (3) | N1—C8—C9—C3 | 0.5 (4) |
C8—N1—C2—C3 | 0.1 (4) | N1—C8—C9—C4 | −179.3 (3) |
C2—N1—C8—C9 | −0.3 (4) | C7—C8—C9—C3 | −179.9 (3) |
S1—N1—C2—C1 | −9.2 (5) | S1—C10—C11—C12 | −179.7 (3) |
C8—N1—C2—C1 | 177.1 (3) | C15—C10—C11—C12 | −1.4 (6) |
C2—N1—C8—C7 | −180.0 (4) | S1—C10—C15—C14 | 179.5 (3) |
S1—N1—C8—C9 | −174.5 (2) | C11—C10—C15—C14 | 1.3 (6) |
Br2—C1—C2—C3 | −88.8 (4) | C10—C11—C12—C13 | 0.7 (7) |
Br2—C1—C2—N1 | 94.7 (4) | C11—C12—C13—C14 | 0.2 (8) |
N1—C2—C3—C9 | 0.2 (4) | C12—C13—C14—C15 | −0.3 (8) |
C1—C2—C3—C9 | −176.8 (3) | C13—C14—C15—C10 | −0.5 (7) |
N1—C2—C3—Br1 | −179.3 (2) | | |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z+1; (iii) −x, −y, −z; (iv) x+1, y+1, z; (v) x, y, z−1; (vi) −x+1, −y, −z; (vii) x, y−1, z; (viii) −x, −y−1, −z; (ix) −x, −y, −z+1; (x) −x, −y−1, −z+1; (xi) x, y, z+1; (xii) x−1, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O2 | 0.97 | 2.20 | 2.866 (5) | 124 |
C1—H1B···Br1 | 0.97 | 2.92 | 3.300 (4) | 104 |
C7—H7···O1 | 0.93 | 2.48 | 3.016 (5) | 117 |
C11—H11···O1 | 0.93 | 2.53 | 2.900 (5) | 104 |