4-Bromo-N-cyclo-hexyl-benzene-sulfonamide.

The title compound, C(12)H(16)BrNO(2)S, adopts an L-shaped conformation with the central C-S-N-C torsion angle being -77.8 (3)°. The crystal packing features N-H⋯O hydrogen bonds, which lead to C(4) chains propagating in [010]; the second O atom is involved in short intra-molecular C-H⋯O contacts.

Related literature

For related structures and background information on sulfon­amides, see: Khan et al. (2010 ▶); Sharif et al. (2010 ▶).

Experimental

Crystal data

C12H16BrNO2S

M = 318.24

Monoclinic,

a = 11.2539 (5) Å

b = 6.2575 (3) Å

c = 19.9743 (10) Å

β = 97.214 (3)°

V = 1395.48 (11) Å3

Z = 4

Mo Kα radiation

μ = 3.09 mm−1

T = 293 K

0.24 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.218, T max = 0.529

12505 measured reflections

3199 independent reflections

1620 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.132

S = 1.01

3199 reflections

157 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026796/hb5542sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026796/hb5542Isup2.hkl

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

C12H16BrNO2S	F(000) = 648
Mr = 318.24	Dx = 1.515 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2185 reflections
a = 11.2539 (5) Å	θ = 2.6–20.1°
b = 6.2575 (3) Å	µ = 3.09 mm−1
c = 19.9743 (10) Å	T = 293 K
β = 97.214 (3)°	Prism, colourless
V = 1395.48 (11) Å3	0.24 × 0.12 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	3199 independent reflections
Radiation source: fine-focus sealed tube	1620 reflections with I > 2σ(I)
graphite	Rint = 0.048
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.218, Tmax = 0.529	k = −7→8
12505 measured reflections	l = −25→23

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0552P)2 + 0.4435P] where P = (Fo2 + 2Fc2)/3
3199 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.52 e Å−3
1 restraint	Δρmin = −0.46 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
Br1	0.03064 (5)	1.13493 (9)	0.90414 (3)	0.1022 (3)
S1	0.32555 (8)	0.51051 (14)	0.73331 (5)	0.0523 (3)
O1	0.4205 (2)	0.4370 (4)	0.78229 (16)	0.0763 (9)
O2	0.2437 (2)	0.3587 (3)	0.70013 (15)	0.0685 (8)
N1	0.3875 (3)	0.6368 (4)	0.67782 (17)	0.0497 (8)
H1N	0.450 (2)	0.714 (5)	0.6936 (17)	0.060*
C1	0.2414 (3)	0.6900 (5)	0.77706 (17)	0.0435 (8)
C2	0.1289 (3)	0.6312 (6)	0.7906 (2)	0.0584 (10)
H2	0.0958	0.5019	0.7746	0.070*
C3	0.0658 (3)	0.7644 (7)	0.8278 (2)	0.0660 (11)
H3	−0.0102	0.7259	0.8372	0.079*
C4	0.1155 (3)	0.9538 (6)	0.8508 (2)	0.0582 (10)
C5	0.2265 (4)	1.0149 (6)	0.8369 (2)	0.0597 (10)
H5	0.2586	1.1454	0.8524	0.072*
C6	0.2899 (3)	0.8824 (6)	0.8000 (2)	0.0555 (10)
H6	0.3655	0.9223	0.7904	0.067*
C7	0.3239 (3)	0.7049 (5)	0.61271 (19)	0.0515 (9)
H7	0.2584	0.6039	0.6000	0.062*
C8	0.4105 (5)	0.6910 (9)	0.5601 (3)	0.0944 (16)
H8A	0.4799	0.7797	0.5739	0.113*
H8B	0.4376	0.5446	0.5569	0.113*
C9	0.3511 (6)	0.7641 (13)	0.4915 (3)	0.121 (2)
H9A	0.4100	0.7639	0.4599	0.146*
H9B	0.2886	0.6634	0.4751	0.146*
C10	0.2986 (5)	0.9797 (11)	0.4935 (3)	0.1082 (19)
H10A	0.2572	1.0147	0.4493	0.130*
H10B	0.3623	1.0833	0.5043	0.130*
C11	0.2126 (5)	0.9940 (9)	0.5448 (3)	0.1004 (17)
H11A	0.1436	0.9042	0.5310	0.121*
H11B	0.1848	1.1402	0.5474	0.121*
C12	0.2716 (4)	0.9235 (7)	0.6137 (2)	0.0770 (13)
H12A	0.3344	1.0241	0.6297	0.092*
H12B	0.2126	0.9260	0.6452	0.092*

	U11	U22	U33	U12	U13	U23
Br1	0.0808 (4)	0.1222 (5)	0.1086 (5)	0.0104 (3)	0.0315 (3)	−0.0430 (3)
S1	0.0472 (5)	0.0401 (5)	0.0703 (7)	0.0070 (4)	0.0101 (5)	0.0059 (5)
O1	0.0616 (17)	0.0779 (19)	0.088 (2)	0.0278 (15)	0.0053 (16)	0.0236 (16)
O2	0.0717 (18)	0.0390 (14)	0.098 (2)	−0.0085 (13)	0.0227 (17)	−0.0093 (13)
N1	0.0382 (16)	0.0525 (18)	0.058 (2)	−0.0045 (13)	0.0052 (15)	−0.0051 (15)
C1	0.0385 (19)	0.0442 (19)	0.047 (2)	0.0044 (16)	0.0015 (16)	0.0099 (16)
C2	0.043 (2)	0.052 (2)	0.079 (3)	−0.0051 (18)	0.003 (2)	−0.003 (2)
C3	0.040 (2)	0.076 (3)	0.083 (3)	0.001 (2)	0.010 (2)	0.001 (2)
C4	0.052 (2)	0.070 (3)	0.053 (3)	0.012 (2)	0.0077 (19)	−0.006 (2)
C5	0.065 (2)	0.058 (2)	0.058 (3)	−0.007 (2)	0.014 (2)	−0.007 (2)
C6	0.050 (2)	0.057 (2)	0.062 (3)	−0.0101 (18)	0.0186 (19)	−0.0018 (19)
C7	0.044 (2)	0.051 (2)	0.059 (3)	−0.0072 (17)	0.0042 (19)	−0.0070 (18)
C8	0.098 (4)	0.127 (4)	0.062 (3)	0.026 (3)	0.024 (3)	−0.016 (3)
C9	0.118 (5)	0.192 (7)	0.057 (4)	0.009 (5)	0.024 (3)	−0.018 (4)
C10	0.083 (4)	0.158 (6)	0.084 (4)	−0.013 (4)	0.012 (3)	0.046 (4)
C11	0.104 (4)	0.113 (4)	0.085 (4)	0.023 (3)	0.015 (3)	0.034 (3)
C12	0.095 (3)	0.071 (3)	0.066 (3)	0.021 (2)	0.016 (3)	0.008 (2)

Br1—C4	1.893 (4)	C7—C12	1.490 (5)
S1—O2	1.427 (3)	C7—C8	1.523 (5)
S1—O1	1.431 (3)	C7—H7	0.9800
S1—N1	1.591 (3)	C8—C9	1.518 (8)
S1—C1	1.769 (3)	C8—H8A	0.9700
N1—C7	1.467 (5)	C8—H8B	0.9700
N1—H1N	0.88 (3)	C9—C10	1.475 (8)
C1—C6	1.376 (5)	C9—H9A	0.9700
C1—C2	1.378 (5)	C9—H9B	0.9700
C2—C3	1.372 (5)	C10—C11	1.499 (7)
C2—H2	0.9300	C10—H10A	0.9700
C3—C4	1.366 (6)	C10—H10B	0.9700
C3—H3	0.9300	C11—C12	1.517 (6)
C4—C5	1.369 (5)	C11—H11A	0.9700
C5—C6	1.368 (5)	C11—H11B	0.9700
C5—H5	0.9300	C12—H12A	0.9700
C6—H6	0.9300	C12—H12B	0.9700
O2—S1—O1	119.11 (17)	C8—C7—H7	108.1
O2—S1—N1	108.71 (17)	C9—C8—C7	111.0 (4)
O1—S1—N1	106.31 (17)	C9—C8—H8A	109.4
O2—S1—C1	107.33 (16)	C7—C8—H8A	109.4
O1—S1—C1	105.45 (17)	C9—C8—H8B	109.4
N1—S1—C1	109.69 (15)	C7—C8—H8B	109.4
C7—N1—S1	123.6 (2)	H8A—C8—H8B	108.0
C7—N1—H1N	116 (2)	C10—C9—C8	112.5 (5)
S1—N1—H1N	115 (2)	C10—C9—H9A	109.1
C6—C1—C2	120.3 (3)	C8—C9—H9A	109.1
C6—C1—S1	120.4 (3)	C10—C9—H9B	109.1
C2—C1—S1	119.3 (3)	C8—C9—H9B	109.1
C3—C2—C1	119.7 (3)	H9A—C9—H9B	107.8
C3—C2—H2	120.2	C9—C10—C11	111.6 (5)
C1—C2—H2	120.2	C9—C10—H10A	109.3
C2—C3—C4	119.5 (4)	C11—C10—H10A	109.3
C2—C3—H3	120.3	C9—C10—H10B	109.3
C4—C3—H3	120.3	C11—C10—H10B	109.3
C5—C4—C3	121.3 (4)	H10A—C10—H10B	108.0
C5—C4—Br1	119.0 (3)	C10—C11—C12	110.9 (4)
C3—C4—Br1	119.7 (3)	C10—C11—H11A	109.5
C6—C5—C4	119.4 (4)	C12—C11—H11A	109.5
C6—C5—H5	120.3	C10—C11—H11B	109.5
C4—C5—H5	120.3	C12—C11—H11B	109.5
C5—C6—C1	119.9 (3)	H11A—C11—H11B	108.0
C5—C6—H6	120.1	C7—C12—C11	112.5 (4)
C1—C6—H6	120.1	C7—C12—H12A	109.1
N1—C7—C12	113.8 (3)	C11—C12—H12A	109.1
N1—C7—C8	108.2 (3)	C7—C12—H12B	109.1
C12—C7—C8	110.5 (4)	C11—C12—H12B	109.1
N1—C7—H7	108.1	H12A—C12—H12B	107.8
C12—C7—H7	108.1
O2—S1—N1—C7	39.2 (3)	Br1—C4—C5—C6	178.2 (3)
O1—S1—N1—C7	168.6 (3)	C4—C5—C6—C1	0.3 (6)
C1—S1—N1—C7	−77.8 (3)	C2—C1—C6—C5	0.6 (6)
O2—S1—C1—C6	−164.1 (3)	S1—C1—C6—C5	−176.5 (3)
O1—S1—C1—C6	68.0 (3)	S1—N1—C7—C12	91.1 (4)
N1—S1—C1—C6	−46.1 (3)	S1—N1—C7—C8	−145.7 (3)
O2—S1—C1—C2	18.8 (4)	N1—C7—C8—C9	−178.8 (4)
O1—S1—C1—C2	−109.1 (3)	C12—C7—C8—C9	−53.5 (6)
N1—S1—C1—C2	136.8 (3)	C7—C8—C9—C10	54.4 (7)
C6—C1—C2—C3	−0.8 (6)	C8—C9—C10—C11	−55.0 (7)
S1—C1—C2—C3	176.3 (3)	C9—C10—C11—C12	54.5 (7)
C1—C2—C3—C4	0.1 (6)	N1—C7—C12—C11	176.7 (4)
C2—C3—C4—C5	0.8 (7)	C8—C7—C12—C11	54.8 (5)
C2—C3—C4—Br1	−178.4 (3)	C10—C11—C12—C7	−55.3 (6)
C3—C4—C5—C6	−1.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.53	2.903 (4)	104
C7—H7···O2	0.98	2.54	2.992 (4)	108
N1—H1n···O1i	0.88 (3)	2.03 (3)	2.898 (4)	169 (3)

Table 1

Hydrogen bonds and short intramolecular contacts (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2	0.93	2.53	2.903 (4)	104
C7—H7⋯O2	0.98	2.54	2.992 (4)	108
N1—H1n⋯O1i	0.88 (3)	2.03 (3)	2.898 (4)	169 (3)

Symmetry code: (i) .