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In the title compound, C19H15BrN2O4S, the indole ring system is planar and the S atom has a distorted tetrahedral configuration. The dihedral angle between the sulfonyl-bound phenyl ring and the indole ring system is 71.19 (8)°. The orientations of the phenyl­sulfonyl and methyl­pyrrolidine-2,5-dione substituents with respect to the indole moiety are influenced by intramolecular C—H...O and C—H...Br interactions. The pyrrolidine ring adopts an extremely flattened envelope conformation. Weak C—H...O interactions generate rings of motifs S(5), S(6), R21(5) and R22(9).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024954/wn6191sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024954/wn6191Isup2.hkl
Contains datablock I

CCDC reference: 227869

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.025
  • wR factor = 0.071
  • Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C16 = 2.96 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

1-(3-Bromo-1-phenylsulfonyl-1H-indol-2-ylmethyl)-pyrrolidine-2,5-dione top
Crystal data top
C19H15BrN2O4SF(000) = 904
Mr = 447.30Dx = 1.636 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6536 reflections
a = 11.4561 (5) Åθ = 2.4–28.2°
b = 15.1588 (7) ŵ = 2.41 mm1
c = 11.6819 (5) ÅT = 293 K
β = 116.493 (1)°Block, yellow
V = 1815.65 (14) Å30.58 × 0.42 × 0.40 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
4435 independent reflections
Radiation source: fine-focus sealed tube3837 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.4°
ω scansh = 1315
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2013
Tmin = 0.287, Tmax = 0.382l = 1515
11117 measured reflections
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)] = 0.026H-atom parameters constrained
wR(F2) = 0.071 w = 1/[σ2(Fo2) + (0.0359P)2 + 0.5632P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4435 reflectionsΔρmax = 0.28 e Å3
245 parametersΔρmin = 0.44 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0086 (6)
Special details top

Experimental. 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 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
xyzUiso*/Ueq
Br10.693042 (19)0.317961 (13)0.513413 (19)0.04797 (8)
S10.32789 (4)0.11116 (2)0.11800 (3)0.02715 (9)
O10.24114 (12)0.18474 (8)0.07634 (12)0.0384 (3)
O20.36123 (13)0.06762 (8)0.02846 (11)0.0414 (3)
O30.41767 (13)0.15540 (11)0.52188 (14)0.0546 (4)
O40.10358 (13)0.30528 (9)0.19258 (14)0.0486 (3)
N10.46774 (11)0.14616 (8)0.23594 (12)0.0262 (2)
N20.28091 (12)0.23007 (8)0.34121 (12)0.0277 (3)
C10.48541 (14)0.22058 (9)0.31667 (14)0.0255 (3)
C20.61502 (14)0.23000 (10)0.38996 (14)0.0278 (3)
C30.68499 (15)0.16156 (10)0.36280 (15)0.0284 (3)
C40.81730 (16)0.13963 (13)0.41362 (17)0.0385 (4)
H40.88040.17420.47660.046*
C50.85142 (17)0.06522 (13)0.3676 (2)0.0446 (4)
H50.93870.04900.40140.053*
C60.75794 (18)0.01384 (12)0.2716 (2)0.0430 (4)
H60.78450.03560.24230.052*
C70.62675 (17)0.03441 (11)0.21879 (18)0.0369 (4)
H70.56460.00010.15450.044*
C80.59177 (14)0.10913 (10)0.26643 (14)0.0266 (3)
C90.26462 (15)0.03279 (10)0.18707 (14)0.0291 (3)
C100.13103 (16)0.03258 (13)0.14548 (16)0.0409 (4)
H100.07860.07570.08960.049*
C110.07684 (19)0.03385 (16)0.18937 (19)0.0530 (5)
H110.01280.03550.16220.064*
C120.1554 (2)0.09677 (15)0.27259 (19)0.0548 (5)
H120.11860.14110.30110.066*
C130.2880 (2)0.09485 (15)0.3142 (2)0.0585 (6)
H130.34030.13760.37100.070*
C140.34431 (18)0.02972 (13)0.27206 (19)0.0456 (4)
H140.43410.02810.30050.055*
C150.37913 (15)0.27755 (10)0.31684 (16)0.0296 (3)
H15A0.41790.32280.38160.036*
H15B0.33590.30690.23460.036*
C160.30911 (16)0.17301 (11)0.44331 (16)0.0328 (3)
C170.18181 (17)0.13910 (12)0.43492 (16)0.0368 (4)
H17A0.17890.14590.51620.044*
H17B0.16990.07730.41090.044*
C180.07776 (17)0.19551 (12)0.33221 (19)0.0406 (4)
H18A0.01290.15870.26680.049*
H18B0.03450.23280.36910.049*
C190.14935 (15)0.25068 (11)0.27656 (16)0.0329 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04806 (12)0.04465 (12)0.04639 (12)0.01466 (8)0.01677 (9)0.01905 (8)
S10.03059 (18)0.02760 (18)0.02245 (17)0.00364 (13)0.01110 (14)0.00045 (13)
O10.0374 (6)0.0353 (6)0.0350 (6)0.0035 (5)0.0093 (5)0.0087 (5)
O20.0531 (7)0.0460 (7)0.0307 (6)0.0090 (6)0.0235 (6)0.0094 (5)
O30.0394 (7)0.0724 (10)0.0484 (8)0.0106 (7)0.0163 (6)0.0240 (7)
O40.0357 (6)0.0511 (8)0.0575 (8)0.0118 (6)0.0194 (6)0.0193 (7)
N10.0250 (6)0.0242 (6)0.0308 (6)0.0019 (5)0.0137 (5)0.0050 (5)
N20.0272 (6)0.0287 (6)0.0313 (6)0.0014 (5)0.0169 (5)0.0003 (5)
C10.0296 (7)0.0230 (7)0.0284 (7)0.0029 (5)0.0170 (6)0.0023 (6)
C20.0298 (7)0.0280 (7)0.0289 (7)0.0060 (6)0.0160 (6)0.0046 (6)
C30.0282 (7)0.0312 (8)0.0310 (7)0.0020 (6)0.0179 (6)0.0030 (6)
C40.0270 (8)0.0485 (10)0.0420 (9)0.0022 (7)0.0171 (7)0.0050 (8)
C50.0336 (9)0.0486 (11)0.0598 (11)0.0102 (7)0.0284 (8)0.0164 (9)
C60.0465 (10)0.0331 (9)0.0648 (12)0.0099 (7)0.0387 (9)0.0068 (8)
C70.0419 (9)0.0278 (8)0.0490 (10)0.0002 (6)0.0276 (8)0.0037 (7)
C80.0276 (7)0.0259 (7)0.0325 (7)0.0001 (5)0.0189 (6)0.0025 (6)
C90.0315 (7)0.0296 (7)0.0257 (7)0.0086 (6)0.0122 (6)0.0025 (6)
C100.0311 (8)0.0517 (10)0.0336 (8)0.0092 (7)0.0089 (7)0.0011 (8)
C110.0376 (9)0.0749 (14)0.0452 (10)0.0265 (9)0.0173 (8)0.0087 (10)
C120.0611 (12)0.0582 (13)0.0465 (11)0.0304 (10)0.0251 (10)0.0003 (9)
C130.0581 (12)0.0523 (12)0.0618 (13)0.0077 (10)0.0237 (10)0.0242 (10)
C140.0373 (9)0.0459 (10)0.0516 (10)0.0020 (8)0.0179 (8)0.0174 (9)
C150.0318 (7)0.0237 (7)0.0388 (8)0.0003 (6)0.0207 (6)0.0018 (6)
C160.0355 (8)0.0339 (8)0.0327 (8)0.0025 (6)0.0185 (7)0.0011 (6)
C170.0439 (9)0.0343 (8)0.0384 (9)0.0076 (7)0.0238 (7)0.0021 (7)
C180.0314 (8)0.0459 (10)0.0494 (10)0.0043 (7)0.0225 (8)0.0000 (8)
C190.0286 (7)0.0335 (8)0.0385 (8)0.0018 (6)0.0168 (6)0.0005 (7)
Geometric parameters (Å, º) top
Br1—C21.8726 (15)C7—C81.397 (2)
S1—O21.4256 (12)C7—H70.93
S1—O11.4273 (12)C9—C141.382 (2)
S1—N11.6665 (12)C9—C101.384 (2)
S1—C91.7633 (15)C10—C111.395 (3)
O3—C161.201 (2)C10—H100.93
O4—C191.210 (2)C11—C121.373 (3)
N1—C81.4175 (18)C11—H110.93
N1—C11.4258 (18)C12—C131.373 (3)
N2—C191.3871 (19)C12—H120.93
N2—C161.390 (2)C13—C141.384 (3)
N2—C151.4666 (19)C13—H130.93
C1—C21.351 (2)C14—H140.93
C1—C151.493 (2)C15—H15A0.97
C2—C31.430 (2)C15—H15B0.97
C3—C41.399 (2)C16—C171.508 (2)
C3—C81.402 (2)C17—C181.522 (3)
C4—C51.379 (3)C17—H17A0.97
C4—H40.93C17—H17B0.97
C5—C61.392 (3)C18—C191.507 (2)
C5—H50.93C18—H18A0.97
C6—C71.382 (2)C18—H18B0.97
C6—H60.93
O2—S1—O1119.03 (8)C9—C10—C11118.46 (18)
O2—S1—N1106.30 (7)C9—C10—H10120.8
O1—S1—N1107.43 (7)C11—C10—H10120.8
O2—S1—C9108.86 (7)C12—C11—C10120.20 (18)
O1—S1—C9108.46 (8)C12—C11—H11119.9
N1—S1—C9106.02 (7)C10—C11—H11119.9
C8—N1—C1108.45 (11)C11—C12—C13120.54 (18)
C8—N1—S1124.60 (10)C11—C12—H12119.7
C1—N1—S1126.82 (10)C13—C12—H12119.7
C19—N2—C16112.81 (13)C12—C13—C14120.5 (2)
C19—N2—C15121.68 (13)C12—C13—H13119.8
C16—N2—C15124.56 (13)C14—C13—H13119.8
C2—C1—N1107.12 (12)C9—C14—C13118.77 (18)
C2—C1—C15127.20 (13)C9—C14—H14120.6
N1—C1—C15125.67 (13)C13—C14—H14120.6
C1—C2—C3110.44 (13)N2—C15—C1114.40 (12)
C1—C2—Br1125.13 (11)N2—C15—H15A108.7
C3—C2—Br1124.41 (11)C1—C15—H15A108.7
C4—C3—C8119.93 (15)N2—C15—H15B108.7
C4—C3—C2133.34 (15)C1—C15—H15B108.7
C8—C3—C2106.72 (13)H15A—C15—H15B107.6
C5—C4—C3118.08 (17)O3—C16—N2124.01 (15)
C5—C4—H4121.0O3—C16—C17128.01 (16)
C3—C4—H4121.0N2—C16—C17107.98 (14)
C4—C5—C6121.43 (16)C16—C17—C18104.74 (13)
C4—C5—H5119.3C16—C17—H17A110.8
C6—C5—H5119.3C18—C17—H17A110.8
C7—C6—C5121.73 (16)C16—C17—H17B110.8
C7—C6—H6119.1C18—C17—H17B110.8
C5—C6—H6119.1H17A—C17—H17B108.9
C6—C7—C8116.94 (16)C19—C18—C17105.45 (13)
C6—C7—H7121.5C19—C18—H18A110.7
C8—C7—H7121.5C17—C18—H18A110.7
C7—C8—C3121.88 (14)C19—C18—H18B110.7
C7—C8—N1130.87 (14)C17—C18—H18B110.7
C3—C8—N1107.24 (12)H18A—C18—H18B108.8
C14—C9—C10121.57 (15)O4—C19—N2124.63 (15)
C14—C9—S1121.08 (12)O4—C19—C18127.39 (15)
C10—C9—S1117.19 (13)N2—C19—C18107.96 (14)
O2—S1—N1—C823.42 (14)S1—N1—C8—C3174.70 (10)
O1—S1—N1—C8151.86 (12)O2—S1—C9—C1470.94 (16)
C9—S1—N1—C892.33 (13)O1—S1—C9—C14158.16 (15)
O2—S1—N1—C1151.95 (12)N1—S1—C9—C1443.05 (16)
O1—S1—N1—C123.50 (14)O2—S1—C9—C10104.44 (14)
C9—S1—N1—C192.31 (13)O1—S1—C9—C1026.45 (15)
C8—N1—C1—C21.95 (16)N1—S1—C9—C10141.57 (13)
S1—N1—C1—C2174.03 (11)C14—C9—C10—C111.3 (3)
C8—N1—C1—C15179.07 (13)S1—C9—C10—C11174.07 (14)
S1—N1—C1—C155.0 (2)C9—C10—C11—C120.5 (3)
N1—C1—C2—C31.76 (17)C10—C11—C12—C130.4 (3)
C15—C1—C2—C3179.28 (14)C11—C12—C13—C140.4 (4)
N1—C1—C2—Br1179.91 (10)C10—C9—C14—C131.3 (3)
C15—C1—C2—Br10.9 (2)S1—C9—C14—C13173.93 (17)
C1—C2—C3—C4177.51 (17)C12—C13—C14—C90.4 (4)
Br1—C2—C3—C40.8 (3)C19—N2—C15—C1140.86 (14)
C1—C2—C3—C80.91 (17)C16—N2—C15—C151.1 (2)
Br1—C2—C3—C8179.26 (10)C2—C1—C15—N2123.55 (16)
C8—C3—C4—C51.0 (2)N1—C1—C15—N257.7 (2)
C2—C3—C4—C5177.26 (17)C19—N2—C16—O3170.09 (17)
C3—C4—C5—C61.2 (3)C15—N2—C16—O31.1 (3)
C4—C5—C6—C70.6 (3)C19—N2—C16—C1710.26 (18)
C5—C6—C7—C80.3 (3)C15—N2—C16—C17179.20 (13)
C6—C7—C8—C30.4 (2)O3—C16—C17—C18170.18 (19)
C6—C7—C8—N1178.06 (15)N2—C16—C17—C1810.18 (18)
C4—C3—C8—C70.2 (2)C16—C17—C18—C196.67 (18)
C2—C3—C8—C7178.48 (14)C16—N2—C19—O4172.64 (17)
C4—C3—C8—N1179.01 (13)C15—N2—C19—O43.3 (2)
C2—C3—C8—N10.33 (16)C16—N2—C19—C185.79 (19)
C1—N1—C8—C7177.27 (16)C15—N2—C19—C18175.09 (14)
S1—N1—C8—C76.6 (2)C17—C18—C19—O4179.40 (18)
C1—N1—C8—C31.39 (16)C17—C18—C19—N21.03 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O20.932.362.901 (2)117
C10—H10···O10.932.552.911 (2)104
C15—H15A···Br10.972.833.349 (1)115
C15—H15B···O10.972.502.900 (2)105
C15—H15B···O40.972.482.857 (2)103
C4—H4···O4i0.932.703.541 (2)152
C7—H7···O2ii0.932.823.333 (3)115
C6—H6···O2ii0.932.883.377 (2)115
C6—H6···O4iii0.932.683.478 (2)145
C12—H12···O4iv0.932.703.500 (3)144
C14—H14···O3v0.932.793.317 (2)117
C13—H13···O3v0.932.503.181 (2)131
C15—H15A···O2vi0.972.673.481 (2)142
C17—H17A···O1vi0.972.673.053 (2)104
C17—H17A···O4vi0.972.673.603 (3)162
C18—H18B···O1vi0.972.813.189 (2)104
C17—H17B···Cg40.972.873.635 (2)136
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y, z; (iii) x+1, y1/2, z+1/2; (iv) x, y1/2, z+1/2; (v) x+1, y, z+1; (vi) x, y+1/2, z+1/2.
List of graph-set motifs generated by pairs of hydrogen bonds top
Hydrogen bond 1Hydrogen bond 2Ring
C7—H7···O2-S(6)
C10—H10···O1-S(5)
C15—H15A···Br1-S(5)
C15—H15B···O1-S(6)
C15—H15B···O4-S(5)
C7—H7···O2iiC6—H6···O2iiR21(5)
C14—H14···O3vC13—H13···O3vR21(5)
C17—H17A···O1viC18—H18B···O1viR21(5)
C15—H15A···O2viC17—H17A···O1viR22(9)
C15—H15A···O2viC18—H18B···O1viR22(9)
Symmetry codes are as given in Table 2.
 

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