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The phenyl ring in the title compound, C15H11Br2NO2S, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700880X/bt2275sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680700880X/bt2275Isup2.hkl
Contains datablock I

CCDC reference: 640286

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.030
  • wR factor = 0.077
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

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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

Computing details top

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-1H-indole top
Crystal data top
C15H11Br2NO2SZ = 2
Mr = 429.12F(000) = 420
Triclinic, P1Dx = 1.883 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5730 (1) ÅCell parameters from 25 reflections
b = 9.5220 (1) Åθ = 2.2–25.0°
c = 10.9660 (2) ŵ = 5.50 mm1
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 tubeRint = 0.019
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω–2θ scansh = 18
Absorption correction: ψ scan
(North et al., 1968)
k = 1111
Tmin = 0.272, Tmax = 0.438l = 1313
3303 measured reflections1 standard reflections every 100 reflections
2645 independent reflections intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-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 reflectionsΔρmax = 0.48 e Å3
191 parametersΔρmin = 0.45 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
Br10.35276 (6)0.31835 (4)0.39733 (4)0.0514 (2)
Br20.23060 (6)0.03929 (6)0.05669 (4)0.0688 (2)
S10.30122 (12)0.29130 (10)0.24780 (9)0.0405 (3)
O10.3639 (4)0.3726 (3)0.3278 (3)0.0524 (10)
O20.3914 (4)0.2711 (3)0.1384 (3)0.0536 (10)
N10.3079 (4)0.1229 (3)0.3349 (3)0.0337 (9)
C10.4225 (5)0.0404 (4)0.1808 (3)0.0438 (12)
C20.3502 (4)0.0142 (4)0.2991 (3)0.0332 (11)
C30.3198 (4)0.1177 (4)0.3972 (3)0.0331 (11)
C40.2111 (5)0.1104 (4)0.6182 (3)0.0405 (12)
C50.1544 (5)0.0149 (5)0.6944 (3)0.0456 (14)
C60.1456 (5)0.1349 (5)0.6533 (4)0.0464 (14)
C70.1944 (5)0.1940 (4)0.5365 (3)0.0410 (12)
C80.2505 (4)0.0976 (4)0.4586 (3)0.0308 (10)
C90.2587 (4)0.0536 (4)0.4982 (3)0.0314 (10)
C100.0710 (5)0.3666 (4)0.2072 (4)0.0402 (11)
C110.0224 (6)0.4645 (4)0.2718 (4)0.0546 (16)
C120.2031 (6)0.5236 (5)0.2386 (5)0.0663 (19)
C130.2868 (6)0.4865 (5)0.1424 (5)0.0638 (19)
C140.1929 (6)0.3913 (5)0.0782 (5)0.0633 (17)
C150.0129 (6)0.3298 (4)0.1084 (4)0.0505 (14)
H1A0.488900.034900.147100.0520*
H1B0.506100.134500.196100.0520*
H40.217700.210600.645800.0480*
H50.121400.050800.774500.0550*
H60.105400.197100.706700.0560*
H70.190100.294200.510700.0490*
H110.035000.490400.336700.0650*
H120.267900.589100.282000.0800*
H130.408300.526400.120900.0760*
H140.251200.367200.012600.0760*
H150.050800.265200.063700.0610*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0549 (3)0.0318 (2)0.0680 (3)0.0053 (2)0.0051 (2)0.0153 (2)
Br20.0598 (3)0.1072 (4)0.0467 (3)0.0144 (3)0.0001 (2)0.0357 (3)
S10.0346 (5)0.0350 (5)0.0486 (6)0.0112 (4)0.0010 (4)0.0023 (4)
O10.0466 (16)0.0384 (14)0.074 (2)0.0186 (13)0.0054 (14)0.0074 (14)
O20.0466 (17)0.0570 (18)0.0510 (17)0.0129 (14)0.0146 (13)0.0051 (14)
N10.0355 (16)0.0286 (15)0.0351 (16)0.0062 (13)0.0028 (13)0.0032 (13)
C10.036 (2)0.056 (2)0.041 (2)0.0068 (18)0.0049 (17)0.0164 (19)
C20.0263 (18)0.039 (2)0.0336 (19)0.0042 (15)0.0004 (15)0.0088 (17)
C30.0301 (18)0.0261 (17)0.041 (2)0.0018 (14)0.0018 (16)0.0063 (16)
C40.041 (2)0.039 (2)0.039 (2)0.0105 (17)0.0003 (17)0.0005 (17)
C50.044 (2)0.062 (3)0.031 (2)0.014 (2)0.0049 (17)0.0075 (19)
C60.043 (2)0.060 (3)0.041 (2)0.008 (2)0.0050 (18)0.024 (2)
C70.044 (2)0.035 (2)0.045 (2)0.0069 (17)0.0020 (18)0.0123 (17)
C80.0256 (17)0.0334 (18)0.0318 (19)0.0051 (15)0.0017 (14)0.0049 (15)
C90.0253 (17)0.0309 (18)0.0363 (19)0.0023 (14)0.0018 (15)0.0073 (15)
C100.038 (2)0.0315 (19)0.046 (2)0.0115 (17)0.0005 (18)0.0070 (17)
C110.048 (3)0.044 (2)0.067 (3)0.004 (2)0.005 (2)0.007 (2)
C120.047 (3)0.050 (3)0.096 (4)0.001 (2)0.004 (3)0.011 (3)
C130.040 (3)0.048 (3)0.091 (4)0.007 (2)0.009 (2)0.010 (3)
C140.057 (3)0.053 (3)0.072 (3)0.014 (2)0.024 (2)0.005 (2)
C150.051 (3)0.045 (2)0.051 (2)0.012 (2)0.004 (2)0.0016 (19)
Geometric parameters (Å, º) top
Br1—C31.877 (4)C10—C111.378 (6)
Br2—C11.975 (4)C10—C151.389 (6)
S1—O11.419 (3)C11—C121.385 (7)
S1—O21.417 (3)C12—C131.366 (7)
S1—N11.677 (3)C13—C141.359 (7)
S1—C101.761 (4)C14—C151.379 (7)
N1—C21.418 (5)C1—H1A0.9701
N1—C81.417 (5)C1—H1B0.9699
C1—C21.464 (5)C4—H40.9298
C2—C31.355 (5)C5—H50.9302
C3—C91.413 (5)C6—H60.9296
C4—C51.372 (6)C7—H70.9307
C4—C91.395 (5)C11—H110.9295
C5—C61.391 (7)C12—H120.9299
C6—C71.374 (5)C13—H130.9298
C7—C81.391 (5)C14—H140.9305
C8—C91.403 (5)C15—H150.9304
Br1···O1i3.176 (3)C6···H1Bii3.0923
Br1···O1ii3.563 (3)C11···H73.0265
Br2···Br2iii3.5724 (7)C11···H4ix3.0649
Br1···H43.2167C12···H4ix3.0099
Br1···H12iv3.1913C12···H6x3.0686
Br1···H1B2.9234C13···H4ix3.0731
Br2···H5v3.2220C15···H5ix2.9755
Br2···H152.9653H1A···S12.9981
Br2···H1Avi3.1034H1A···O22.2048
S1···H1A2.9981H1A···Br2vi3.1034
S1···H73.0181H1B···Br12.9234
O1···Br1vii3.176 (3)H1B···C6ii3.0923
O1···C73.016 (5)H4···Br13.2167
O1···Br1ii3.563 (3)H4···C11ix3.0649
O2···C12.866 (5)H4···C12ix3.0099
O2···C13viii3.417 (6)H4···C13ix3.0731
O1···H112.5325H5···Br2xi3.2220
O1···H72.4795H5···C15ix2.9755
O2···H1A2.2048H6···C12x3.0686
O2···H152.7107H7···S13.0181
C1···O22.866 (5)H7···O12.4795
C1···C6ii3.579 (5)H7···C113.0265
C4···C8ix3.557 (5)H7···H112.4679
C6···C1ii3.579 (5)H11···O12.5325
C7···O13.016 (5)H11···H72.4679
C7···C113.581 (5)H12···Br1xii3.1913
C8···C4ix3.557 (5)H15···Br22.9653
C11···C73.581 (5)H15···O22.7107
C13···O2viii3.417 (6)
O1—S1—O2120.48 (19)C10—C11—C12119.0 (4)
O1—S1—N1106.32 (17)C11—C12—C13120.4 (4)
O1—S1—C10108.22 (19)C12—C13—C14120.1 (4)
O2—S1—N1106.30 (17)C13—C14—C15121.2 (5)
O2—S1—C10109.1 (2)C10—C15—C14118.4 (4)
N1—S1—C10105.43 (17)Br2—C1—H1A109.16
S1—N1—C2128.7 (3)Br2—C1—H1B109.14
S1—N1—C8123.1 (2)C2—C1—H1A109.12
C2—N1—C8107.9 (3)C2—C1—H1B109.20
Br2—C1—C2112.2 (3)H1A—C1—H1B107.90
N1—C2—C1126.5 (3)C5—C4—H4120.83
N1—C2—C3107.2 (3)C9—C4—H4120.76
C1—C2—C3126.2 (3)C4—C5—H5119.56
Br1—C3—C2124.3 (3)C6—C5—H5119.65
Br1—C3—C9125.0 (3)C5—C6—H6118.87
C2—C3—C9110.8 (3)C7—C6—H6118.90
C5—C4—C9118.4 (3)C6—C7—H7121.40
C4—C5—C6120.8 (3)C8—C7—H7121.49
C5—C6—C7122.2 (4)C10—C11—H11120.50
C6—C7—C8117.1 (4)C12—C11—H11120.53
N1—C8—C7131.0 (3)C11—C12—H12119.78
N1—C8—C9107.6 (3)C13—C12—H12119.77
C7—C8—C9121.4 (3)C12—C13—H13119.91
C3—C9—C4133.5 (4)C14—C13—H13119.96
C3—C9—C8106.5 (3)C13—C14—H14119.37
C4—C9—C8120.1 (3)C15—C14—H14119.38
S1—C10—C11119.5 (3)C10—C15—H15120.82
S1—C10—C15119.7 (3)C14—C15—H15120.81
C11—C10—C15120.8 (4)
O1—S1—N1—C2144.5 (3)C1—C2—C3—Br13.7 (5)
O1—S1—N1—C842.7 (3)C2—C3—C9—C80.4 (4)
O2—S1—N1—C215.0 (4)Br1—C3—C9—C8179.1 (2)
O2—S1—N1—C8172.2 (3)C2—C3—C9—C4179.3 (4)
C10—S1—N1—C2100.8 (3)Br1—C3—C9—C41.2 (5)
C10—S1—N1—C872.1 (3)C9—C4—C5—C60.4 (6)
N1—S1—C10—C11100.7 (3)C5—C4—C9—C80.9 (5)
O1—S1—C10—C15165.5 (3)C5—C4—C9—C3179.4 (4)
O2—S1—C10—C1532.7 (4)C4—C5—C6—C70.7 (6)
N1—S1—C10—C1581.1 (4)C5—C6—C7—C81.2 (6)
O1—S1—C10—C1112.8 (4)C6—C7—C8—C90.7 (5)
O2—S1—C10—C11145.5 (3)C6—C7—C8—N1179.7 (4)
S1—N1—C8—C75.9 (5)C7—C8—C9—C40.4 (5)
S1—N1—C2—C3173.8 (3)N1—C8—C9—C30.5 (4)
C8—N1—C2—C30.1 (4)N1—C8—C9—C4179.3 (3)
C2—N1—C8—C90.3 (4)C7—C8—C9—C3179.9 (3)
S1—N1—C2—C19.2 (5)S1—C10—C11—C12179.7 (3)
C8—N1—C2—C1177.1 (3)C15—C10—C11—C121.4 (6)
C2—N1—C8—C7180.0 (4)S1—C10—C15—C14179.5 (3)
S1—N1—C8—C9174.5 (2)C11—C10—C15—C141.3 (6)
Br2—C1—C2—C388.8 (4)C10—C11—C12—C130.7 (7)
Br2—C1—C2—N194.7 (4)C11—C12—C13—C140.2 (8)
N1—C2—C3—C90.2 (4)C12—C13—C14—C150.3 (8)
C1—C2—C3—C9176.8 (3)C13—C14—C15—C100.5 (7)
N1—C2—C3—Br1179.3 (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, z1; (vi) x+1, y, z; (vii) x, y1, z; (viii) x, y1, z; (ix) x, y, z+1; (x) x, y1, z+1; (xi) x, y, z+1; (xii) x1, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O20.972.202.866 (5)124
C1—H1B···Br10.972.923.300 (4)104
C7—H7···O10.932.483.016 (5)117
C11—H11···O10.932.532.900 (5)104
 

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