2,3-Bis(dibromo­meth­yl)-1-(phenyl­sulfon­yl)-1H-indole

In the structure of the title compound, C₁₆H₁₁Br₄NO₂S, the two dibromo­methyl groups are rotated in a such a way as to minimize their mutual inter­actions. The dihedral angle between the phenyl­sulfonyl group and the mean plane of the indole ring is 86.1 (7)°. The non-fused pyrrole C-C bond length is 1.362 (3)Å, the S-N distance is 1.685 (4)Å, and the average S=O distance is 1.424 (3)Å.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.023
• wR factor = 0.042
• Data-to-parameter ratio = 24.7

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br4    ..  O2      ..       3.27 Ang.

   2 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

   2 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT-NT (Bruker, 2006); data reduction: SAINT-NT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CRYSTALS.

2,3-Bis(dibromomethyl)-1-(phenylsulfonyl)-1H-indole

Crystal data

C16H11Br4NO2S	F(000) = 1144
Mr = 600.95	Dx = 2.200 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5701 (3) Å	Cell parameters from 7015 reflections
b = 17.3004 (6) Å	θ = 2–30°
c = 10.9621 (4) Å	µ = 9.00 mm^−1
β = 91.5878 (15)°	T = 120 K
V = 1814.26 (11) Å^3	Prism, colorless
Z = 4	0.42 × 0.39 × 0.32 mm

Data collection

Bruker-Nonius Kappa Apex2 diffractometer	3962 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 30.3°, θmin = 2.4°
Absorption correction: numerical (de Meulenaer & Tompa, 1965)	h = −13→13
Tmin = 0.03, Tmax = 0.06	k = −24→24
24244 measured reflections	l = −15→8
5383 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.023	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are 7.56, 7.82 and 2.08
wR(F^2) = 0.042	(Δ/σ)max = 0.001
S = 1.01	Δρmax = 1.13 e Å^−3
5383 reflections	Δρmin = −1.04 e Å^−3
218 parameters	Extinction correction: Larson (1970), Equation 22
0 restraints	Extinction coefficient: 8.2 (7)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. ¹H NMR (CDCl₃): δ 8.18 (d, 2H, J = 8.0 Hz), 7.98 (s, 1H), 7.83 (d, 2H, J = 7.5 Hz), 7.70 (s, 1H), 7.59 (t, 1H, J = 7.5 Hz), 7.48–7.41 (m, 4H); ¹³C NMR (CDCl₃): δ 137.4, 136.0, 135.0, 130.8, 129.7 (2 C), 127.9, 127.5, 127.4, 127.0 (2 C), 124.4, 122.3, 115.6, 29.9, 23.9; MS m/z: 601, 522, 442, 378, 298, 220, 141, 105, 77

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.55553 (3)	0.097063 (16)	0.56736 (2)	0.0175
Br2	0.64738 (4)	−0.030354 (19)	0.76608 (3)	0.0284
Br3	0.72420 (3)	0.138514 (19)	1.00871 (3)	0.0232
Br4	0.62536 (3)	0.270770 (16)	0.82218 (3)	0.0193
S1	0.16350 (7)	0.00343 (4)	0.75199 (6)	0.0164
O1	0.0590 (2)	−0.01580 (13)	0.8368 (2)	0.0255
O2	0.2371 (2)	−0.05644 (11)	0.6920 (2)	0.0216
N1	0.2847 (2)	0.05540 (13)	0.8306 (2)	0.0136
C2	0.4214 (3)	0.07322 (15)	0.7928 (2)	0.0141
C3	0.4739 (3)	0.13136 (15)	0.8642 (2)	0.0120
C4	0.3692 (3)	0.15424 (15)	0.9485 (2)	0.0135
C5	0.3692 (3)	0.20828 (16)	1.0436 (2)	0.0168
C6	0.2505 (3)	0.21427 (17)	1.1122 (3)	0.0201
C7	0.1353 (3)	0.16698 (18)	1.0881 (3)	0.0213
C8	0.1327 (3)	0.11271 (17)	0.9964 (3)	0.0184
C9	0.2521 (3)	0.10705 (15)	0.9261 (2)	0.0144
C10	0.0924 (3)	0.06775 (16)	0.6441 (3)	0.0167
C11	0.1462 (3)	0.07010 (18)	0.5274 (3)	0.0211
C12	0.0887 (3)	0.12126 (19)	0.4434 (3)	0.0255
C13	−0.0202 (3)	0.16875 (19)	0.4755 (3)	0.0268
C14	−0.0737 (3)	0.16607 (18)	0.5907 (3)	0.0252
C15	−0.0174 (3)	0.11531 (18)	0.6772 (3)	0.0222
C16	0.4924 (3)	0.02930 (15)	0.6968 (2)	0.0156
C17	0.6186 (3)	0.16072 (15)	0.8581 (2)	0.0144
H51	0.4529	0.2415	1.0610	0.0198*
H61	0.2476	0.2531	1.1797	0.0243*
H71	0.0515	0.1725	1.1399	0.0259*
H81	0.0492	0.0791	0.9804	0.0214*
H111	0.2246	0.0351	0.5051	0.0255*
H121	0.1262	0.1239	0.3593	0.0311*
H131	−0.0607	0.2058	0.4141	0.0317*
H141	−0.1534	0.2004	0.6121	0.0304*
H151	−0.0543	0.1131	0.7616	0.0266*
H161	0.4232	−0.0078	0.6598	0.0187*
H171	0.6650	0.1328	0.7903	0.0167*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02532 (14)	0.01435 (12)	0.01283 (12)	−0.00162 (11)	0.00248 (10)	0.00028 (10)
Br2	0.03795 (19)	0.02371 (16)	0.02393 (15)	0.01822 (14)	0.00552 (13)	0.00559 (12)
Br3	0.01927 (14)	0.02720 (16)	0.02262 (14)	−0.00284 (12)	−0.00860 (11)	0.00445 (12)
Br4	0.02396 (14)	0.01468 (13)	0.01922 (13)	−0.00597 (11)	0.00104 (10)	0.00182 (11)
S1	0.0169 (3)	0.0128 (3)	0.0194 (3)	−0.0062 (2)	−0.0043 (2)	0.0025 (3)
O1	0.0204 (11)	0.0278 (12)	0.0284 (11)	−0.0130 (9)	−0.0005 (9)	0.0063 (9)
O2	0.0244 (11)	0.0116 (9)	0.0283 (11)	−0.0025 (8)	−0.0069 (9)	−0.0027 (8)
N1	0.0122 (10)	0.0134 (10)	0.0152 (10)	−0.0028 (8)	−0.0010 (8)	0.0011 (8)
C2	0.0147 (12)	0.0126 (12)	0.0151 (12)	−0.0026 (9)	−0.0007 (9)	0.0024 (9)
C3	0.0129 (11)	0.0106 (11)	0.0123 (11)	0.0006 (9)	−0.0018 (9)	0.0004 (9)
C4	0.0157 (12)	0.0106 (12)	0.0143 (12)	0.0010 (9)	0.0001 (9)	0.0017 (9)
C5	0.0198 (13)	0.0131 (12)	0.0175 (13)	0.0000 (10)	0.0002 (10)	0.0003 (10)
C6	0.0253 (15)	0.0179 (14)	0.0175 (13)	0.0060 (11)	0.0060 (11)	−0.0011 (11)
C7	0.0207 (14)	0.0225 (14)	0.0212 (14)	0.0051 (11)	0.0083 (11)	0.0056 (12)
C8	0.0136 (12)	0.0219 (14)	0.0196 (13)	−0.0014 (10)	0.0009 (10)	0.0041 (11)
C9	0.0151 (12)	0.0135 (12)	0.0146 (12)	0.0004 (10)	0.0001 (10)	0.0031 (10)
C10	0.0136 (12)	0.0159 (13)	0.0202 (13)	−0.0039 (10)	−0.0052 (10)	0.0023 (10)
C11	0.0196 (14)	0.0243 (15)	0.0189 (13)	0.0038 (11)	−0.0046 (11)	−0.0015 (11)
C12	0.0293 (16)	0.0283 (16)	0.0186 (14)	0.0036 (13)	−0.0060 (12)	0.0021 (12)
C13	0.0238 (16)	0.0262 (16)	0.0298 (17)	0.0009 (13)	−0.0136 (13)	0.0058 (13)
C14	0.0153 (14)	0.0210 (15)	0.0392 (18)	0.0025 (11)	−0.0027 (12)	0.0021 (13)
C15	0.0166 (13)	0.0218 (15)	0.0283 (15)	−0.0022 (11)	0.0014 (12)	0.0027 (12)
C16	0.0218 (13)	0.0095 (11)	0.0154 (12)	−0.0007 (10)	0.0020 (10)	0.0022 (10)
C17	0.0131 (12)	0.0154 (12)	0.0144 (12)	−0.0017 (10)	−0.0026 (9)	0.0002 (10)

Geometric parameters (Å, º)

Br1—C16	1.949 (3)	C6—H61	1.000
Br2—C16	1.944 (3)	C7—C8	1.375 (4)
Br3—C17	1.950 (3)	C7—H71	1.000
Br4—C17	1.946 (3)	C8—C9	1.399 (4)
S1—O1	1.424 (2)	C8—H81	1.000
S1—O2	1.424 (2)	C10—C11	1.393 (4)
S1—N1	1.685 (2)	C10—C15	1.391 (4)
S1—C10	1.748 (3)	C11—C12	1.380 (4)
N1—C2	1.418 (3)	C11—H111	1.000
N1—C9	1.417 (3)	C12—C13	1.379 (5)
C2—C3	1.362 (3)	C12—H121	1.000
C2—C16	1.479 (4)	C13—C14	1.377 (5)
C3—C4	1.437 (4)	C13—H131	1.000
C3—C17	1.479 (4)	C14—C15	1.390 (4)
C4—C5	1.400 (4)	C14—H141	1.000
C4—C9	1.403 (4)	C15—H151	1.000
C5—C6	1.384 (4)	C16—H161	1.000
C5—H51	1.000	C17—H171	1.000
C6—C7	1.392 (4)
O1—S1—O2	119.82 (13)	C4—C9—C8	121.5 (3)
O1—S1—N1	106.02 (12)	S1—C10—C11	119.5 (2)
O2—S1—N1	106.38 (12)	S1—C10—C15	118.8 (2)
O1—S1—C10	108.89 (14)	C11—C10—C15	121.6 (3)
O2—S1—C10	109.80 (13)	C10—C11—C12	118.7 (3)
N1—S1—C10	104.83 (12)	C10—C11—H111	120.3
S1—N1—C2	126.43 (18)	C12—C11—H111	121.0
S1—N1—C9	123.48 (18)	C11—C12—C13	120.2 (3)
C2—N1—C9	107.6 (2)	C11—C12—H121	119.8
N1—C2—C3	108.7 (2)	C13—C12—H121	120.1
N1—C2—C16	122.8 (2)	C12—C13—C14	121.1 (3)
C3—C2—C16	128.3 (2)	C12—C13—H131	119.5
C2—C3—C4	108.7 (2)	C14—C13—H131	119.4
C2—C3—C17	123.9 (2)	C13—C14—C15	120.0 (3)
C4—C3—C17	127.3 (2)	C13—C14—H141	120.0
C3—C4—C5	132.6 (2)	C15—C14—H141	120.0
C3—C4—C9	107.1 (2)	C10—C15—C14	118.5 (3)
C5—C4—C9	120.2 (2)	C10—C15—H151	120.6
C4—C5—C6	118.1 (3)	C14—C15—H151	120.9
C4—C5—H51	120.6	C2—C16—Br2	110.79 (18)
C6—C5—H51	121.2	C2—C16—Br1	111.52 (18)
C5—C6—C7	120.7 (3)	Br2—C16—Br1	110.79 (13)
C5—C6—H61	119.5	C2—C16—H161	107.8
C7—C6—H61	119.8	Br2—C16—H161	107.9
C6—C7—C8	122.6 (3)	Br1—C16—H161	107.9
C6—C7—H71	118.7	C3—C17—Br4	112.44 (18)
C8—C7—H71	118.8	C3—C17—Br3	110.96 (18)
C7—C8—C9	116.9 (3)	Br4—C17—Br3	110.18 (13)
C7—C8—H81	121.6	C3—C17—H171	107.7
C9—C8—H81	121.5	Br4—C17—H171	107.7
N1—C9—C4	107.8 (2)	Br3—C17—H171	107.7
N1—C9—C8	130.6 (2)