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The title compound, C20H15BrN2O2S, is a new bioactive indole derivative with the 4-bromo­benzene­sulfonate moiety as a good leaving group. The S atom of the 4-bromo­benzene­sulfonate moiety is bonded to the amine N atom in sp3 hybridization, with an S—N bond length of 1.616 (3) Å. The mol­ecules are connected by N—H...O hydrogen bonds, forming one-dimensional columns along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004404/ob6351sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004404/ob6351Isup2.hkl
Contains datablock I

CCDC reference: 238699

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.043
  • wR factor = 0.108
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 1997b); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4-Bromo-N-(2-phenyl-1H-indol-7-yl)benzenesulfonamide top
Crystal data top
C20H15BrN2O2SF(000) = 1728
Mr = 427.31Dx = 1.562 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 30.764 (14) ÅCell parameters from 2144 reflections
b = 4.922 (2) Åθ = 2.7–21.7°
c = 26.335 (13) ŵ = 2.40 mm1
β = 114.332 (8)°T = 298 K
V = 3633 (3) Å3Bar, colourless
Z = 80.40 × 0.20 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3524 independent reflections
Radiation source: fine-focus sealed tube2106 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997a)
h = 3737
Tmin = 0.607, Tmax = 0.698k = 65
15353 measured reflectionsl = 3232
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0552P)2]
where P = (Fo2 + 2Fc2)/3
3524 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.75 e Å3
0 restraintsΔρmin = 0.48 e Å3
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. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 20 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set is over 99% complete. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible.

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
xyzUiso*/Ueq
Br10.035975 (15)0.16015 (11)0.185976 (17)0.0892 (2)
S10.20783 (3)0.18035 (16)0.41436 (3)0.0392 (2)
O10.19605 (7)0.0927 (5)0.45857 (9)0.0522 (6)
O20.21876 (8)0.4562 (4)0.40998 (9)0.0513 (6)
N10.25367 (8)0.0034 (5)0.41938 (9)0.0370 (6)
H10.24660.17450.41820.044*
N20.33162 (8)0.4082 (5)0.44433 (10)0.0376 (6)
H2B0.31960.42750.47000.045*
C10.08611 (11)0.0514 (8)0.25395 (13)0.0545 (9)
C20.09056 (12)0.1726 (8)0.30264 (15)0.0600 (10)
H2A0.06860.30290.30250.072*
C30.12774 (11)0.1001 (7)0.35179 (14)0.0519 (9)
H3A0.13120.18140.38510.062*
C40.15975 (10)0.0937 (6)0.35122 (12)0.0388 (7)
C50.15456 (12)0.2150 (8)0.30206 (14)0.0538 (9)
H5A0.17610.34740.30210.065*
C60.11761 (13)0.1418 (8)0.25276 (15)0.0608 (10)
H6A0.11410.22200.21930.073*
C70.31332 (10)0.2441 (6)0.39825 (12)0.0351 (7)
C80.27683 (10)0.0553 (6)0.38262 (12)0.0376 (7)
C90.26606 (12)0.0899 (6)0.33427 (13)0.0462 (8)
H8A0.24180.21850.32320.055*
C100.29172 (12)0.0441 (7)0.30159 (13)0.0525 (9)
H9A0.28360.13990.26850.063*
C110.32828 (13)0.1385 (7)0.31756 (14)0.0518 (9)
H10A0.34510.16580.29560.062*
C120.34029 (11)0.2835 (7)0.36681 (13)0.0430 (8)
C130.37682 (11)0.4699 (7)0.39809 (13)0.0478 (8)
H12A0.40060.53390.38800.057*
C140.37140 (10)0.5387 (6)0.44461 (13)0.0409 (7)
C150.39993 (11)0.7197 (6)0.49081 (13)0.0419 (8)
C160.44886 (12)0.7380 (8)0.50572 (15)0.0579 (10)
H16A0.46250.63690.48630.070*
C170.47709 (13)0.9019 (9)0.54840 (16)0.0696 (12)
H17A0.50980.90940.55820.084*
C180.45725 (14)1.0559 (9)0.57699 (15)0.0657 (11)
H18A0.47631.16910.60590.079*
C190.40928 (13)1.0413 (7)0.56263 (14)0.0559 (9)
H19A0.39571.14600.58170.067*
C200.38083 (12)0.8720 (6)0.52002 (13)0.0454 (8)
H20A0.34830.86150.51110.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0617 (3)0.1247 (5)0.0558 (3)0.0146 (3)0.0012 (2)0.0095 (3)
S10.0418 (5)0.0371 (5)0.0399 (4)0.0078 (4)0.0179 (3)0.0069 (4)
O10.0513 (14)0.0681 (16)0.0441 (13)0.0123 (12)0.0267 (11)0.0105 (11)
O20.0534 (14)0.0305 (13)0.0645 (14)0.0062 (11)0.0187 (11)0.0073 (11)
N10.0425 (14)0.0278 (14)0.0421 (14)0.0070 (12)0.0187 (12)0.0007 (11)
N20.0364 (14)0.0399 (15)0.0398 (14)0.0036 (12)0.0191 (11)0.0005 (12)
C10.0403 (19)0.071 (2)0.0395 (19)0.0013 (18)0.0038 (15)0.0060 (17)
C20.046 (2)0.073 (3)0.056 (2)0.0207 (19)0.0151 (17)0.006 (2)
C30.048 (2)0.059 (2)0.0462 (19)0.0133 (18)0.0169 (16)0.0021 (16)
C40.0372 (17)0.0403 (19)0.0400 (17)0.0007 (15)0.0170 (14)0.0011 (14)
C50.058 (2)0.055 (2)0.051 (2)0.0159 (18)0.0243 (18)0.0020 (17)
C60.063 (2)0.070 (3)0.045 (2)0.002 (2)0.0174 (18)0.0083 (19)
C70.0387 (17)0.0321 (18)0.0345 (16)0.0016 (13)0.0151 (14)0.0034 (13)
C80.0395 (17)0.0345 (17)0.0381 (16)0.0007 (15)0.0153 (14)0.0014 (14)
C90.050 (2)0.0386 (19)0.0473 (19)0.0050 (16)0.0174 (16)0.0042 (15)
C100.064 (2)0.052 (2)0.0416 (18)0.001 (2)0.0218 (17)0.0117 (17)
C110.063 (2)0.054 (2)0.0468 (19)0.0033 (19)0.0318 (18)0.0033 (17)
C120.0444 (19)0.044 (2)0.0471 (19)0.0005 (15)0.0257 (16)0.0016 (15)
C130.0420 (19)0.055 (2)0.051 (2)0.0078 (17)0.0247 (16)0.0019 (17)
C140.0376 (18)0.0395 (19)0.0465 (18)0.0002 (15)0.0183 (15)0.0063 (15)
C150.0410 (18)0.0381 (18)0.0412 (17)0.0077 (15)0.0114 (15)0.0031 (15)
C160.040 (2)0.073 (3)0.060 (2)0.0079 (18)0.0202 (18)0.0044 (19)
C170.042 (2)0.093 (3)0.063 (2)0.025 (2)0.0108 (19)0.005 (2)
C180.065 (3)0.064 (3)0.050 (2)0.019 (2)0.006 (2)0.0002 (19)
C190.060 (2)0.046 (2)0.056 (2)0.0035 (19)0.0181 (18)0.0053 (18)
C200.0420 (18)0.041 (2)0.0480 (18)0.0016 (15)0.0130 (15)0.0042 (16)
Geometric parameters (Å, º) top
Br1—C11.896 (3)C8—C91.376 (4)
S1—O21.415 (2)C9—C101.405 (5)
S1—O11.421 (2)C9—H8A0.9300
S1—N11.616 (3)C10—C111.364 (5)
S1—C41.763 (3)C10—H9A0.9300
N1—C81.442 (4)C11—C121.390 (4)
N1—H10.9000C11—H10A0.9300
N2—C71.371 (4)C12—C131.421 (4)
N2—C141.380 (4)C13—C141.346 (4)
N2—H2B0.8998C13—H12A0.9300
C1—C61.367 (5)C14—C151.471 (4)
C1—C21.369 (5)C15—C201.368 (4)
C2—C31.375 (5)C15—C161.393 (4)
C2—H2A0.9300C16—C171.365 (5)
C3—C41.375 (4)C16—H16A0.9300
C3—H3A0.9300C17—C181.376 (6)
C4—C51.374 (4)C17—H17A0.9300
C5—C61.375 (5)C18—C191.366 (5)
C5—H5A0.9300C18—H18A0.9300
C6—H6A0.9300C19—C201.382 (4)
C7—C81.383 (4)C19—H19A0.9300
C7—C121.406 (4)C20—H20A0.9300
O2—S1—O1120.50 (14)C8—C9—C10120.1 (3)
O2—S1—N1107.16 (13)C8—C9—H8A120.0
O1—S1—N1106.13 (13)C10—C9—H8A120.0
O2—S1—C4106.88 (14)C11—C10—C9121.1 (3)
O1—S1—C4107.54 (14)C11—C10—H9A119.4
N1—S1—C4108.15 (13)C9—C10—H9A119.4
C8—N1—S1120.39 (19)C10—C11—C12119.6 (3)
C8—N1—H1109.2C10—C11—H10A120.2
S1—N1—H1109.3C12—C11—H10A120.2
C7—N2—C14108.6 (2)C11—C12—C7118.9 (3)
C7—N2—H2B125.6C11—C12—C13135.6 (3)
C14—N2—H2B125.8C7—C12—C13105.4 (3)
C6—C1—C2121.8 (3)C14—C13—C12109.0 (3)
C6—C1—Br1118.9 (3)C14—C13—H12A125.5
C2—C1—Br1119.3 (3)C12—C13—H12A125.5
C1—C2—C3119.5 (3)C13—C14—N2108.7 (3)
C1—C2—H2A120.3C13—C14—C15130.5 (3)
C3—C2—H2A120.3N2—C14—C15120.8 (3)
C2—C3—C4119.4 (3)C20—C15—C16118.1 (3)
C2—C3—H3A120.3C20—C15—C14123.3 (3)
C4—C3—H3A120.3C16—C15—C14118.6 (3)
C5—C4—C3120.4 (3)C17—C16—C15121.1 (4)
C5—C4—S1120.7 (2)C17—C16—H16A119.4
C3—C4—S1118.9 (2)C15—C16—H16A119.4
C4—C5—C6120.4 (3)C16—C17—C18120.1 (4)
C4—C5—H5A119.8C16—C17—H17A120.0
C6—C5—H5A119.8C18—C17—H17A120.0
C1—C6—C5118.6 (3)C19—C18—C17119.5 (4)
C1—C6—H6A120.7C19—C18—H18A120.3
C5—C6—H6A120.7C17—C18—H18A120.3
N2—C7—C8130.3 (3)C18—C19—C20120.5 (4)
N2—C7—C12108.3 (3)C18—C19—H19A119.8
C8—C7—C12121.4 (3)C20—C19—H19A119.8
C9—C8—C7118.7 (3)C15—C20—C19120.8 (3)
C9—C8—N1122.2 (3)C15—C20—H20A119.6
C7—C8—N1119.0 (3)C19—C20—H20A119.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.901.982.872 (3)170
N2—H2B···O1ii0.902.133.009 (4)167
Symmetry codes: (i) x, y1, z; (ii) x+1/2, y+1/2, z+1.
 

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