3-Bromo-2-(2-bromo-4,5-dimethoxy­benz­yl)-1-phenyl­sulfonyl-1H-indole

In the title compound, C₁₉H₁₅BrN₂O₄S, the orientations of the phenyl­sulfonyl and 2-bromo-4,5-dimethoxy­benzyl substituents with respect to the indole moiety are influenced by intra­molecular C—H...O and C—H...Br inter­actions. The sulfonyl-bound phenyl ring forms a dihedral angle of 86.9 (1)° with the mean plane through the indole ring system.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.042
• wR factor = 0.100
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.270     0.513
            Tmin and Tmax expected:      0.211     0.513
            RR =      1.279
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.27
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14    ..  O2      ..       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  BR1     ..       2.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  O4      ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H22A   ..  O1      ..       2.80 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H23B   ..  O1      ..       2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10    ..  CG1     ..       3.07 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15B   ..  CG2     ..       2.91 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

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 and PLATON (Spek, 2003).

3-Bromo-2-(2-bromo-4,5-dimethoxybenzyl)-1-phenylsulfonyl-1H-indole

Crystal data

C23H19Br2NO4S	Z = 2
Mr = 565.27	F(000) = 564
Triclinic, P1	Dx = 1.662 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7855 (7) Å	Cell parameters from 2278 reflections
b = 9.8033 (7) Å	θ = 2.3–25.4°
c = 14.874 (1) Å	µ = 3.71 mm^−1
α = 88.368 (1)°	T = 293 K
β = 79.065 (1)°	Block, colourless
γ = 64.090 (1)°	0.44 × 0.40 × 0.18 mm
V = 1129.21 (15) Å^3

Data collection

Siemens SMART CCD area-detector diffractometer	5306 independent reflections
Radiation source: fine-focus sealed tube	3299 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 2.3°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.270, Tmax = 0.513	l = −19→10
7173 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0335P)^2 + 0.7566P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
5306 reflections	Δρmax = 0.43 e Å^−3
283 parameters	Δρmin = −0.45 e Å^−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0063 (7)

Special details

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 10 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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.37722 (5)	0.23193 (6)	0.02147 (4)	0.07181 (18)
Br2	0.09178 (6)	0.69246 (4)	0.33812 (3)	0.06279 (16)
S1	−0.31059 (12)	0.49389 (10)	0.20146 (6)	0.0488 (3)
O1	−0.2960 (4)	0.6086 (3)	0.24996 (19)	0.0681 (8)
O2	−0.4577 (3)	0.5286 (3)	0.16195 (19)	0.0665 (8)
O3	0.3117 (4)	0.0203 (3)	0.34661 (19)	0.0602 (8)
O4	0.3386 (4)	0.1626 (3)	0.48135 (17)	0.0546 (7)
N1	−0.1398 (3)	0.4262 (3)	0.11391 (18)	0.0381 (7)
C1	0.0304 (4)	0.4050 (4)	0.1174 (2)	0.0397 (8)
C2	0.1382 (4)	0.2994 (4)	0.0501 (2)	0.0405 (8)
C3	0.0471 (4)	0.2467 (3)	0.0019 (2)	0.0340 (7)
C4	0.0974 (5)	0.1423 (4)	−0.0721 (2)	0.0456 (9)
H4	0.2133	0.0874	−0.0990	0.055*
C5	−0.0280 (5)	0.1221 (4)	−0.1045 (3)	0.0531 (10)
H5	0.0033	0.0515	−0.1532	0.064*
C6	−0.2006 (5)	0.2058 (5)	−0.0655 (3)	0.0540 (10)
H6	−0.2832	0.1917	−0.0897	0.065*
C7	−0.2540 (4)	0.3087 (4)	0.0078 (2)	0.0466 (9)
H7	−0.3704	0.3640	0.0334	0.056*
C8	−0.1269 (4)	0.3272 (4)	0.0422 (2)	0.0345 (7)
C9	−0.2831 (5)	0.3410 (4)	0.2715 (2)	0.0459 (9)
C10	−0.2132 (6)	0.3313 (5)	0.3487 (3)	0.0616 (11)
H10	−0.1797	0.4047	0.3629	0.074*
C11	−0.1934 (6)	0.2129 (6)	0.4043 (3)	0.0769 (14)
H11	−0.1465	0.2061	0.4562	0.092*
C12	−0.2423 (6)	0.1056 (5)	0.3836 (4)	0.0749 (14)
H12	−0.2280	0.0255	0.4215	0.090*
C13	−0.3124 (6)	0.1139 (5)	0.3077 (4)	0.0744 (14)
H13	−0.3448	0.0395	0.2941	0.089*
C14	−0.3351 (5)	0.2336 (5)	0.2508 (3)	0.0601 (11)
H14	−0.3845	0.2411	0.1997	0.072*
C15	0.0757 (5)	0.4912 (4)	0.1805 (3)	0.0482 (9)
H15A	−0.0253	0.5861	0.2016	0.058*
H15B	0.1647	0.5161	0.1459	0.058*
C16	0.1389 (4)	0.4088 (3)	0.2637 (2)	0.0378 (8)
C17	0.1919 (4)	0.2515 (4)	0.2677 (2)	0.0427 (8)
H17	0.1830	0.1985	0.2196	0.051*
C18	0.2560 (4)	0.1741 (4)	0.3401 (2)	0.0413 (8)
C19	0.2692 (4)	0.2501 (4)	0.4134 (2)	0.0395 (8)
C20	0.2167 (5)	0.4052 (4)	0.4114 (2)	0.0443 (9)
H20	0.2237	0.4584	0.4600	0.053*
C21	0.1540 (4)	0.4804 (3)	0.3371 (2)	0.0388 (8)
C22	0.3138 (7)	−0.0638 (4)	0.2708 (3)	0.0759 (14)
H22A	0.3610	−0.1697	0.2825	0.114*
H22B	0.3837	−0.0488	0.2171	0.114*
H22C	0.1982	−0.0301	0.2610	0.114*
C23	0.3676 (6)	0.2347 (5)	0.5538 (3)	0.0622 (11)
H23A	0.4205	0.1606	0.5958	0.093*
H23B	0.2595	0.3119	0.5857	0.093*
H23C	0.4425	0.2800	0.5288	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0384 (2)	0.0891 (4)	0.0913 (4)	−0.0290 (2)	−0.0192 (2)	0.0130 (3)
Br2	0.0992 (4)	0.0327 (2)	0.0632 (3)	−0.0297 (2)	−0.0301 (2)	0.00682 (18)
S1	0.0516 (6)	0.0383 (5)	0.0408 (5)	−0.0073 (4)	−0.0045 (4)	0.0004 (4)
O1	0.099 (2)	0.0405 (15)	0.0540 (18)	−0.0233 (15)	−0.0091 (16)	−0.0034 (13)
O2	0.0399 (14)	0.0726 (19)	0.0614 (19)	−0.0021 (13)	−0.0091 (13)	0.0077 (15)
O3	0.090 (2)	0.0284 (13)	0.0709 (19)	−0.0219 (13)	−0.0488 (16)	0.0128 (12)
O4	0.0779 (18)	0.0424 (14)	0.0435 (15)	−0.0191 (13)	−0.0317 (14)	0.0114 (12)
N1	0.0401 (15)	0.0372 (15)	0.0354 (16)	−0.0141 (13)	−0.0114 (13)	0.0060 (12)
C1	0.046 (2)	0.0364 (18)	0.045 (2)	−0.0202 (16)	−0.0249 (17)	0.0169 (16)
C2	0.0337 (17)	0.043 (2)	0.046 (2)	−0.0164 (16)	−0.0143 (16)	0.0128 (17)
C3	0.0355 (17)	0.0335 (17)	0.0346 (19)	−0.0149 (15)	−0.0119 (15)	0.0077 (14)
C4	0.044 (2)	0.045 (2)	0.041 (2)	−0.0159 (17)	−0.0036 (17)	0.0027 (17)
C5	0.069 (3)	0.052 (2)	0.043 (2)	−0.030 (2)	−0.014 (2)	−0.0054 (18)
C6	0.052 (2)	0.076 (3)	0.050 (2)	−0.040 (2)	−0.018 (2)	0.001 (2)
C7	0.0374 (19)	0.060 (2)	0.043 (2)	−0.0218 (18)	−0.0089 (17)	0.0014 (18)
C8	0.0359 (17)	0.0363 (17)	0.0322 (18)	−0.0154 (15)	−0.0101 (15)	0.0035 (14)
C9	0.045 (2)	0.043 (2)	0.037 (2)	−0.0129 (17)	0.0015 (17)	0.0016 (16)
C10	0.078 (3)	0.060 (3)	0.051 (3)	−0.035 (2)	−0.012 (2)	0.012 (2)
C11	0.089 (3)	0.077 (3)	0.060 (3)	−0.032 (3)	−0.017 (3)	0.025 (3)
C12	0.072 (3)	0.058 (3)	0.076 (4)	−0.020 (2)	0.003 (3)	0.025 (3)
C13	0.078 (3)	0.064 (3)	0.081 (4)	−0.040 (3)	0.010 (3)	−0.001 (3)
C14	0.063 (3)	0.066 (3)	0.051 (3)	−0.033 (2)	−0.001 (2)	0.002 (2)
C15	0.067 (2)	0.0385 (19)	0.054 (2)	−0.0294 (19)	−0.034 (2)	0.0132 (17)
C16	0.0460 (19)	0.0295 (16)	0.045 (2)	−0.0198 (15)	−0.0190 (16)	0.0081 (15)
C17	0.058 (2)	0.0326 (17)	0.046 (2)	−0.0206 (17)	−0.0276 (18)	0.0046 (16)
C18	0.047 (2)	0.0287 (17)	0.051 (2)	−0.0150 (16)	−0.0215 (18)	0.0052 (16)
C19	0.0451 (19)	0.0377 (18)	0.0347 (19)	−0.0156 (16)	−0.0128 (16)	0.0059 (15)
C20	0.059 (2)	0.0366 (19)	0.038 (2)	−0.0192 (17)	−0.0172 (18)	0.0007 (16)
C21	0.0471 (19)	0.0280 (16)	0.042 (2)	−0.0156 (15)	−0.0132 (17)	0.0046 (15)
C22	0.101 (4)	0.035 (2)	0.103 (4)	−0.026 (2)	−0.053 (3)	0.001 (2)
C23	0.082 (3)	0.059 (3)	0.048 (2)	−0.024 (2)	−0.035 (2)	0.013 (2)

Geometric parameters (Å, º)

Br1—C2	1.869 (3)	C10—C11	1.373 (6)
Br2—C21	1.904 (3)	C10—H10	0.93
S1—O1	1.417 (3)	C11—C12	1.360 (7)
S1—O2	1.422 (3)	C11—H11	0.93
S1—N1	1.681 (3)	C12—C13	1.369 (7)
S1—C9	1.755 (4)	C12—H12	0.93
O3—C18	1.374 (4)	C13—C14	1.391 (6)
O3—C22	1.408 (5)	C13—H13	0.93
O4—C19	1.362 (4)	C14—H14	0.93
O4—C23	1.425 (4)	C15—C16	1.518 (4)
N1—C8	1.418 (4)	C15—H15A	0.97
N1—C1	1.428 (4)	C15—H15B	0.97
C1—C2	1.347 (5)	C16—C21	1.372 (5)
C1—C15	1.495 (5)	C16—C17	1.406 (4)
C2—C3	1.421 (5)	C17—C18	1.365 (5)
C3—C4	1.393 (5)	C17—H17	0.93
C3—C8	1.395 (4)	C18—C19	1.387 (5)
C4—C5	1.372 (5)	C19—C20	1.384 (4)
C4—H4	0.93	C20—C21	1.378 (5)
C5—C6	1.384 (5)	C20—H20	0.93
C5—H5	0.93	C22—H22A	0.96
C6—C7	1.371 (5)	C22—H22B	0.96
C6—H6	0.93	C22—H22C	0.96
C7—C8	1.393 (5)	C23—H23A	0.96
C7—H7	0.93	C23—H23B	0.96
C9—C14	1.380 (5)	C23—H23C	0.96
C9—C10	1.384 (5)
O1—S1—O2	120.57 (18)	C11—C12—H12	119.6
O1—S1—N1	106.48 (17)	C13—C12—H12	119.6
O2—S1—N1	105.80 (16)	C12—C13—C14	120.0 (5)
O1—S1—C9	108.93 (18)	C12—C13—H13	120.0
O2—S1—C9	108.68 (19)	C14—C13—H13	120.0
N1—S1—C9	105.32 (15)	C9—C14—C13	118.8 (4)
C18—O3—C22	117.6 (3)	C9—C14—H14	120.6
C19—O4—C23	117.6 (3)	C13—C14—H14	120.6
C8—N1—C1	108.0 (3)	C1—C15—C16	115.2 (3)
C8—N1—S1	121.9 (2)	C1—C15—H15A	108.5
C1—N1—S1	125.6 (2)	C16—C15—H15A	108.5
C2—C1—N1	106.5 (3)	C1—C15—H15B	108.5
C2—C1—C15	127.5 (3)	C16—C15—H15B	108.5
N1—C1—C15	125.9 (3)	H15A—C15—H15B	107.5
C1—C2—C3	111.5 (3)	C21—C16—C17	116.2 (3)
C1—C2—Br1	124.7 (3)	C21—C16—C15	122.8 (3)
C3—C2—Br1	123.8 (3)	C17—C16—C15	121.0 (3)
C4—C3—C8	120.3 (3)	C18—C17—C16	121.9 (3)
C4—C3—C2	133.7 (3)	C18—C17—H17	119.0
C8—C3—C2	106.0 (3)	C16—C17—H17	119.0
C5—C4—C3	118.5 (3)	C17—C18—O3	124.1 (3)
C5—C4—H4	120.8	C17—C18—C19	120.4 (3)
C3—C4—H4	120.8	O3—C18—C19	115.5 (3)
C4—C5—C6	120.7 (4)	O4—C19—C20	125.1 (3)
C4—C5—H5	119.7	O4—C19—C18	116.1 (3)
C6—C5—H5	119.7	C20—C19—C18	118.8 (3)
C7—C6—C5	122.2 (3)	C21—C20—C19	119.7 (3)
C7—C6—H6	118.9	C21—C20—H20	120.1
C5—C6—H6	118.9	C19—C20—H20	120.1
C6—C7—C8	117.4 (3)	C16—C21—C20	123.0 (3)
C6—C7—H7	121.3	C16—C21—Br2	120.0 (2)
C8—C7—H7	121.3	C20—C21—Br2	117.0 (3)
C7—C8—C3	121.0 (3)	O3—C22—H22A	109.5
C7—C8—N1	131.0 (3)	O3—C22—H22B	109.5
C3—C8—N1	107.9 (3)	H22A—C22—H22B	109.5
C14—C9—C10	120.4 (4)	O3—C22—H22C	109.5
C14—C9—S1	120.0 (3)	H22A—C22—H22C	109.5
C10—C9—S1	119.5 (3)	H22B—C22—H22C	109.5
C11—C10—C9	119.7 (4)	O4—C23—H23A	109.5
C11—C10—H10	120.2	O4—C23—H23B	109.5
C9—C10—H10	120.2	H23A—C23—H23B	109.5
C12—C11—C10	120.2 (5)	O4—C23—H23C	109.5
C12—C11—H11	119.9	H23A—C23—H23C	109.5
C10—C11—H11	119.9	H23B—C23—H23C	109.5
C11—C12—C13	120.8 (4)
O1—S1—N1—C8	−169.5 (2)	O1—S1—C9—C10	−15.3 (4)
O2—S1—N1—C8	−40.1 (3)	O2—S1—C9—C10	−148.4 (3)
C9—S1—N1—C8	74.9 (3)	N1—S1—C9—C10	98.6 (3)
O1—S1—N1—C1	37.3 (3)	C14—C9—C10—C11	0.8 (6)
O2—S1—N1—C1	166.7 (3)	S1—C9—C10—C11	179.2 (3)
C9—S1—N1—C1	−78.3 (3)	C9—C10—C11—C12	0.0 (7)
C8—N1—C1—C2	0.6 (3)	C10—C11—C12—C13	−0.3 (7)
S1—N1—C1—C2	156.8 (2)	C11—C12—C13—C14	−0.3 (7)
C8—N1—C1—C15	177.4 (3)	C10—C9—C14—C13	−1.4 (6)
S1—N1—C1—C15	−26.3 (4)	S1—C9—C14—C13	−179.8 (3)
N1—C1—C2—C3	−0.8 (4)	C12—C13—C14—C9	1.1 (6)
C15—C1—C2—C3	−177.6 (3)	C2—C1—C15—C16	−83.3 (4)
N1—C1—C2—Br1	178.2 (2)	N1—C1—C15—C16	100.5 (4)
C15—C1—C2—Br1	1.4 (5)	C1—C15—C16—C21	−167.0 (3)
C1—C2—C3—C4	179.0 (3)	C1—C15—C16—C17	15.5 (5)
Br1—C2—C3—C4	0.0 (5)	C21—C16—C17—C18	−0.5 (5)
C1—C2—C3—C8	0.7 (4)	C15—C16—C17—C18	177.2 (3)
Br1—C2—C3—C8	−178.3 (2)	C16—C17—C18—O3	−179.0 (3)
C8—C3—C4—C5	0.6 (5)	C16—C17—C18—C19	0.7 (6)
C2—C3—C4—C5	−177.5 (3)	C22—O3—C18—C17	4.7 (5)
C3—C4—C5—C6	1.2 (5)	C22—O3—C18—C19	−175.1 (4)
C4—C5—C6—C7	−1.6 (6)	C23—O4—C19—C20	−3.3 (5)
C5—C6—C7—C8	0.1 (6)	C23—O4—C19—C18	174.8 (3)
C6—C7—C8—C3	1.7 (5)	C17—C18—C19—O4	−178.5 (3)
C6—C7—C8—N1	177.6 (3)	O3—C18—C19—O4	1.3 (5)
C4—C3—C8—C7	−2.1 (5)	C17—C18—C19—C20	−0.2 (5)
C2—C3—C8—C7	176.5 (3)	O3—C18—C19—C20	179.5 (3)
C4—C3—C8—N1	−178.9 (3)	O4—C19—C20—C21	177.6 (3)
C2—C3—C8—N1	−0.3 (3)	C18—C19—C20—C21	−0.4 (5)
C1—N1—C8—C7	−176.5 (3)	C17—C16—C21—C20	−0.2 (5)
S1—N1—C8—C7	26.2 (5)	C15—C16—C21—C20	−177.8 (3)
C1—N1—C8—C3	−0.2 (3)	C17—C16—C21—Br2	178.4 (2)
S1—N1—C8—C3	−157.5 (2)	C15—C16—C21—Br2	0.8 (5)
O1—S1—C9—C14	163.1 (3)	C19—C20—C21—C16	0.6 (5)
O2—S1—C9—C14	29.9 (3)	C19—C20—C21—Br2	−178.0 (3)
N1—S1—C9—C14	−83.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2	0.93	2.32	2.909 (4)	121
C10—H10···O1	0.93	2.56	2.920 (5)	104
C14—H14···O2	0.93	2.67	2.978 (5)	100
C15—H15A···Br2	0.97	2.85	3.169 (4)	100
C15—H15A···O1	0.97	2.26	2.926 (6)	125
C6—H6···Br1^i	0.93	2.99	3.587 (5)	124
C12—H12···O4^ii	0.93	2.71	3.558 (6)	153
C22—H22A···O1^iii	0.96	2.80	3.492 (5)	130
C23—H23B···O1^iv	0.96	2.70	3.161 (5)	110
C23—H23A···O3^v	0.96	2.54	3.406 (6)	150
C10—H10···Cg1	0.93	3.07	3.632 (6)	120
C15—H15B···Cg2^vi	0.97	2.91	3.506 (4)	121

Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z+1; (iii) x+1, y−1, z; (iv) −x, −y+1, −z+1; (v) −x+1, −y, −z+1; (vi) −x, −y+1, −z.