3,4-Dibromo-2,5-dimethyl-1-phenyl-sulfonyl-1H-pyrrole.

In the title compound, C(12)H(11)Br(2)NO(2)S, the dihedral angle between the two rings is 78.79 (12)°. The crystal packing features C-H⋯π inter-actions.

Related literature

For the biological activity of heterocyclic compounds, see: Ali et al. (1989 ▶); Amal Raj et al. (2003 ▶). For related structures, see: Seshadri et al. (2009 ▶); Gunasekaran et al. (2009 ▶).

Experimental

Crystal data

C12H11Br2NO2S

M = 393.10

Orthorhombic,

a = 6.6248 (4) Å

b = 9.7172 (6) Å

c = 21.2083 (11) Å

V = 1365.27 (14) Å3

Z = 4

Mo Kα radiation

μ = 6.08 mm−1

T = 295 K

0.35 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.945, T max = 0.955

9255 measured reflections

3491 independent reflections

2735 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.075

S = 1.02

3491 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.92 e Å−3

Absolute structure: Flack (1983 ▶), 1460 Friedel pairs

Flack parameter: 0.010 (10)

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global. DOI: 10.1107/S1600536811030443/bt5579sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811030443/bt5579globalsup2.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H11Br2NO2S	F(000) = 768
Mr = 393.10	Dx = 1.912 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7415 reflections
a = 6.6248 (4) Å	θ = 2.0–28.7°
b = 9.7172 (6) Å	µ = 6.08 mm−1
c = 21.2083 (11) Å	T = 295 K
V = 1365.27 (14) Å3	Block, pale brown
Z = 4	0.35 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	3491 independent reflections
Radiation source: fine-focus sealed tube	2735 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 0 pixels mm-1	θmax = 28.6°, θmin = 1.9°
ω and φ scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→10
Tmin = 0.945, Tmax = 0.955	l = −17→28
9255 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.029P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3491 reflections	Δρmax = 0.47 e Å−3
165 parameters	Δρmin = −0.92 e Å−3
0 restraints	Absolute structure: Flack (1983), 1460 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.010 (10)

	x	y	z	Uiso*/Ueq
C1	0.1597 (5)	0.2073 (3)	0.41513 (14)	0.0293 (7)
C2	0.1708 (5)	0.0859 (3)	0.44645 (14)	0.0327 (8)
C3	0.3469 (6)	0.0151 (3)	0.42718 (15)	0.0329 (7)
C4	0.4461 (5)	0.0895 (3)	0.38337 (14)	0.0298 (7)
C5	0.2313 (6)	0.2831 (3)	0.25488 (15)	0.0327 (8)
C6	0.3161 (7)	0.1922 (4)	0.21200 (17)	0.0469 (10)
H6	0.4434	0.1548	0.2190	0.056*
C7	0.2079 (8)	0.1584 (4)	0.15883 (18)	0.0549 (11)
H7	0.2633	0.0990	0.1291	0.066*
C8	0.0186 (8)	0.2121 (4)	0.14939 (18)	0.0596 (13)
H8	−0.0538	0.1877	0.1135	0.072*
C9	−0.0642 (7)	0.3002 (5)	0.19171 (19)	0.0610 (12)
H9	−0.1935	0.3344	0.1850	0.073*
C10	0.0435 (6)	0.3399 (5)	0.24533 (17)	0.0499 (10)
H10	−0.0102	0.4030	0.2738	0.060*
C11	0.0040 (6)	0.3164 (4)	0.42098 (18)	0.0449 (9)
H11A	−0.0988	0.2870	0.4499	0.067*
H11B	−0.0552	0.3336	0.3804	0.067*
H11C	0.0655	0.3993	0.4364	0.067*
C12	0.6350 (6)	0.0542 (4)	0.34928 (18)	0.0474 (10)
H12A	0.6855	−0.0324	0.3643	0.071*
H12B	0.7340	0.1246	0.3565	0.071*
H12C	0.6077	0.0476	0.3049	0.071*
N1	0.3311 (4)	0.2116 (3)	0.37564 (12)	0.0285 (6)
O1	0.2928 (4)	0.4577 (2)	0.34533 (11)	0.0435 (6)
O2	0.5824 (4)	0.3247 (3)	0.30554 (12)	0.0448 (6)
S1	0.37395 (13)	0.33329 (9)	0.32099 (4)	0.03095 (19)
Br1	−0.00952 (7)	0.02664 (5)	0.50804 (2)	0.05823 (14)
Br2	0.43075 (7)	−0.15500 (4)	0.45930 (2)	0.05195 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0269 (18)	0.0320 (17)	0.0290 (17)	0.0039 (15)	0.0017 (15)	−0.0010 (14)
C2	0.0326 (19)	0.0388 (19)	0.0267 (18)	−0.0042 (16)	0.0028 (15)	−0.0001 (14)
C3	0.0411 (19)	0.0277 (16)	0.0299 (17)	0.0031 (15)	−0.0065 (15)	0.0011 (13)
C4	0.032 (2)	0.0269 (15)	0.0301 (17)	0.0053 (15)	−0.0025 (15)	−0.0039 (13)
C5	0.036 (2)	0.0324 (17)	0.0294 (18)	−0.0045 (16)	−0.0004 (15)	0.0039 (14)
C6	0.063 (3)	0.037 (2)	0.041 (2)	0.006 (2)	0.003 (2)	0.0050 (17)
C7	0.081 (3)	0.042 (2)	0.041 (2)	−0.006 (3)	−0.003 (2)	−0.0039 (19)
C8	0.075 (4)	0.068 (3)	0.036 (2)	−0.025 (3)	−0.008 (2)	0.005 (2)
C9	0.040 (2)	0.100 (4)	0.043 (2)	−0.002 (2)	−0.006 (2)	0.008 (2)
C10	0.039 (2)	0.075 (3)	0.036 (2)	0.004 (2)	0.0026 (17)	−0.0014 (18)
C11	0.046 (2)	0.045 (2)	0.044 (2)	0.014 (2)	0.011 (2)	−0.0015 (16)
C12	0.043 (2)	0.040 (2)	0.059 (2)	0.0122 (19)	0.012 (2)	0.0013 (18)
N1	0.0301 (16)	0.0276 (13)	0.0279 (13)	0.0044 (12)	0.0036 (13)	−0.0001 (12)
O1	0.0573 (17)	0.0265 (12)	0.0466 (15)	0.0032 (13)	0.0010 (13)	−0.0011 (11)
O2	0.0325 (13)	0.0490 (15)	0.0528 (15)	−0.0089 (13)	0.0050 (12)	0.0076 (12)
S1	0.0317 (4)	0.0273 (4)	0.0339 (4)	−0.0018 (4)	0.0008 (4)	0.0021 (3)
Br1	0.0557 (3)	0.0637 (3)	0.0552 (2)	0.0000 (2)	0.0204 (2)	0.0186 (2)
Br2	0.0661 (3)	0.03477 (19)	0.0549 (2)	0.0103 (2)	−0.0033 (2)	0.01168 (17)

C1—C2	1.356 (4)	C7—H7	0.9300
C1—N1	1.412 (4)	C8—C9	1.356 (6)
C1—C11	1.484 (5)	C8—H8	0.9300
C2—C3	1.415 (5)	C9—C10	1.397 (5)
C2—Br1	1.861 (3)	C9—H9	0.9300
C3—C4	1.348 (5)	C10—H10	0.9300
C3—Br2	1.872 (3)	C11—H11A	0.9600
C4—N1	1.420 (4)	C11—H11B	0.9600
C4—C12	1.486 (5)	C11—H11C	0.9600
C5—C10	1.377 (5)	C12—H12A	0.9600
C5—C6	1.386 (5)	C12—H12B	0.9600
C5—S1	1.760 (3)	C12—H12C	0.9600
C6—C7	1.376 (5)	N1—S1	1.680 (3)
C6—H6	0.9300	O1—S1	1.420 (2)
C7—C8	1.373 (7)	O2—S1	1.422 (3)
C2—C1—N1	105.8 (3)	C10—C9—H9	119.8
C2—C1—C11	128.2 (3)	C5—C10—C9	118.1 (4)
N1—C1—C11	126.0 (3)	C5—C10—H10	121.0
C1—C2—C3	109.1 (3)	C9—C10—H10	121.0
C1—C2—Br1	125.3 (3)	C1—C11—H11A	109.5
C3—C2—Br1	125.5 (3)	C1—C11—H11B	109.5
C4—C3—C2	109.9 (3)	H11A—C11—H11B	109.5
C4—C3—Br2	125.4 (3)	C1—C11—H11C	109.5
C2—C3—Br2	124.7 (3)	H11A—C11—H11C	109.5
C3—C4—N1	105.4 (3)	H11B—C11—H11C	109.5
C3—C4—C12	128.5 (3)	C4—C12—H12A	109.5
N1—C4—C12	126.1 (3)	C4—C12—H12B	109.5
C10—C5—C6	121.7 (4)	H12A—C12—H12B	109.5
C10—C5—S1	119.4 (3)	C4—C12—H12C	109.5
C6—C5—S1	118.8 (3)	H12A—C12—H12C	109.5
C7—C6—C5	118.6 (4)	H12B—C12—H12C	109.5
C7—C6—H6	120.7	C1—N1—C4	109.8 (3)
C5—C6—H6	120.7	C1—N1—S1	124.5 (2)
C8—C7—C6	120.3 (4)	C4—N1—S1	125.3 (2)
C8—C7—H7	119.8	O1—S1—O2	120.09 (18)
C6—C7—H7	119.8	O1—S1—N1	106.52 (14)
C9—C8—C7	120.9 (4)	O2—S1—N1	106.36 (15)
C9—C8—H8	119.6	O1—S1—C5	108.82 (17)
C7—C8—H8	119.6	O2—S1—C5	108.76 (17)
C8—C9—C10	120.4 (4)	N1—S1—C5	105.30 (15)
C8—C9—H9	119.8
N1—C1—C2—C3	0.2 (4)	C2—C1—N1—C4	0.4 (3)
C11—C1—C2—C3	−178.7 (3)	C11—C1—N1—C4	179.3 (3)
N1—C1—C2—Br1	177.2 (2)	C2—C1—N1—S1	172.8 (2)
C11—C1—C2—Br1	−1.7 (5)	C11—C1—N1—S1	−8.3 (5)
C1—C2—C3—C4	−0.8 (4)	C3—C4—N1—C1	−0.9 (3)
Br1—C2—C3—C4	−177.8 (2)	C12—C4—N1—C1	178.9 (3)
C1—C2—C3—Br2	178.1 (2)	C3—C4—N1—S1	−173.2 (2)
Br1—C2—C3—Br2	1.1 (4)	C12—C4—N1—S1	6.5 (5)
C2—C3—C4—N1	1.0 (4)	C1—N1—S1—O1	33.9 (3)
Br2—C3—C4—N1	−177.9 (2)	C4—N1—S1—O1	−154.8 (3)
C2—C3—C4—C12	−178.7 (3)	C1—N1—S1—O2	163.1 (3)
Br2—C3—C4—C12	2.4 (5)	C4—N1—S1—O2	−25.6 (3)
C10—C5—C6—C7	−0.2 (6)	C1—N1—S1—C5	−81.6 (3)
S1—C5—C6—C7	−176.9 (3)	C4—N1—S1—C5	89.7 (3)
C5—C6—C7—C8	−1.2 (6)	C10—C5—S1—O1	−16.9 (3)
C6—C7—C8—C9	0.8 (6)	C6—C5—S1—O1	159.8 (3)
C7—C8—C9—C10	1.1 (7)	C10—C5—S1—O2	−149.4 (3)
C6—C5—C10—C9	2.0 (6)	C6—C5—S1—O2	27.4 (3)
S1—C5—C10—C9	178.6 (3)	C10—C5—S1—N1	96.9 (3)
C8—C9—C10—C5	−2.4 (7)	C6—C5—S1—N1	−86.3 (3)

Cg2 is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1	0.93	2.57	2.922 (5)	103.
C11—H11A···Br1	0.96	2.88	3.368 (4)	113.
C11—H11C···O1	0.96	2.51	2.849 (5)	100.
C12—H12A···Br2	0.96	2.88	3.378 (4)	113.
C12—H12B···O2	0.96	2.44	2.809 (5)	102.
C12—H12A···Cg2i	0.96	2.85	3.545 (7)	130.

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯Cg2i	0.96	2.85	3.545 (7)	130

Symmetry code: (i) .