N-(3-Chloro-phen-yl)benzene-sulfonamide.

In the crystal structure of the title compound, C(12)H(10)ClNO(2)S, the N-H bond is trans to one of the S=O bonds. The two aromatic rings form a dihedral angle of 65.4 (1)°, compared with a value of 49.1 (1)° in N-(2-chloro-phen-yl)-benzene-sulfonamide. The mol-ecules are connected by inter-molecular N-H⋯O hydrogen bonds into chains running along the b axis.

Related literature

For related literature, see: Gelbrich et al. (2007 ▶); Gowda et al. (2005 ▶, 2008a ▶,b ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C12H10ClNO2S

M = 267.72

Tetragonal,

a = 8.8357 (7) Å

c = 32.081 (5) Å

V = 2504.6 (5) Å3

Z = 8

Cu Kα radiation

μ = 4.18 mm−1

T = 299 (2) K

0.38 × 0.35 × 0.33 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.222, T max = 0.251

5004 measured reflections

2232 independent reflections

2054 reflections with I > 2σ(I)

R int = 0.071

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.10

2232 reflections

158 parameters

19 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 840 Friedel pairs

Flack parameter: −0.01 (2)

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026895/ci2659sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026895/ci2659Isup2.hkl

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

C12H10ClNO2S	Z = 8
Mr = 267.72	F000 = 1104
Tetragonal, P43212	Dx = 1.420 Mg m−3
Hall symbol: P 4nw 2abw	Cu Kα radiation λ = 1.54180 Å
a = 8.8357 (7) Å	Cell parameters from 25 reflections
b = 8.8357 (7) Å	θ = 6.5–18.9º
c = 32.081 (5) Å	µ = 4.18 mm−1
α = 90º	T = 299 (2) K
β = 90º	Prism, colourless
γ = 90º	0.38 × 0.35 × 0.33 mm
V = 2504.6 (5) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.072
Radiation source: fine-focus sealed tube	θmax = 66.8º
Monochromator: graphite	θmin = 5.2º
T = 299(2) K	h = −10→0
ω/2θ scans	k = −10→0
Absorption correction: ψ scan(North et al., 1968)	l = −38→37
Tmin = 0.222, Tmax = 0.251	3 standard reflections
5004 measured reflections	every 120 min
2232 independent reflections	intensity decay: 1.0%
2054 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.0371P)2 + 0.1574P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094	(Δ/σ)max = 0.004
S = 1.10	Δρmax = 0.19 e Å−3
2232 reflections	Δρmin = −0.21 e Å−3
158 parameters	Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
19 restraints	Extinction coefficient: 0.0031 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 840 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.01 (2)

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.

	x	y	z	Uiso*/Ueq
C1	−0.0696 (3)	−0.0170 (3)	0.09615 (8)	0.0566 (6)
C2	−0.2118 (3)	−0.0569 (4)	0.10996 (9)	0.0763 (8)
H2	−0.2603	0.0001	0.1304	0.092*
C3	−0.2814 (4)	−0.1829 (4)	0.09306 (12)	0.1005 (11)
H3	−0.3771	−0.2112	0.1023	0.121*
C4	−0.2119 (5)	−0.2644 (4)	0.06353 (16)	0.1213 (15)
H4	−0.2601	−0.3486	0.0523	0.146*
C5	−0.0724 (5)	−0.2253 (5)	0.04988 (17)	0.1362 (17)
H5	−0.0247	−0.2840	0.0297	0.163*
C6	0.0006 (4)	−0.0978 (4)	0.06576 (12)	0.0987 (12)
H6	0.0951	−0.0688	0.0558	0.118*
C7	−0.0413 (3)	0.3249 (2)	0.05535 (7)	0.0518 (5)
C8	−0.1736 (3)	0.3333 (3)	0.03316 (7)	0.0571 (5)
H8	−0.2659	0.3123	0.0458	0.069*
C9	−0.1672 (3)	0.3736 (3)	−0.00854 (8)	0.0633 (6)
C10	−0.0304 (3)	0.4020 (3)	−0.02766 (8)	0.0685 (7)
H10	−0.0269	0.4276	−0.0558	0.082*
C11	0.1000 (3)	0.3923 (3)	−0.00488 (8)	0.0687 (7)
H11	0.1925	0.4114	−0.0176	0.082*
C12	0.0959 (3)	0.3547 (3)	0.03655 (8)	0.0633 (6)
H12	0.1850	0.3494	0.0519	0.076*
Cl1	−0.33446 (9)	0.38734 (11)	−0.03637 (3)	0.1003 (3)
N1	−0.0492 (2)	0.2925 (2)	0.09923 (6)	0.0542 (5)
H1N	−0.1414 (15)	0.300 (3)	0.1090 (7)	0.065*
O1	−0.0183 (2)	0.1447 (2)	0.16226 (5)	0.0712 (5)
O2	0.17669 (17)	0.1309 (2)	0.10738 (6)	0.0678 (5)
S1	0.02122 (6)	0.13880 (7)	0.119048 (18)	0.05501 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0552 (12)	0.0546 (11)	0.0599 (13)	0.0022 (9)	−0.0124 (11)	0.0011 (11)
C2	0.0731 (16)	0.0876 (19)	0.0681 (16)	−0.0161 (14)	−0.0063 (14)	0.0007 (15)
C3	0.092 (2)	0.093 (2)	0.117 (3)	−0.0326 (19)	−0.020 (2)	0.009 (2)
C4	0.109 (3)	0.075 (2)	0.181 (4)	−0.0087 (19)	−0.027 (3)	−0.033 (2)
C5	0.118 (3)	0.107 (3)	0.184 (4)	0.008 (2)	0.001 (3)	−0.087 (3)
C6	0.0725 (19)	0.098 (2)	0.126 (3)	0.0044 (15)	0.0010 (19)	−0.050 (2)
C7	0.0577 (12)	0.0460 (11)	0.0518 (12)	−0.0002 (9)	0.0055 (11)	−0.0063 (10)
C8	0.0565 (12)	0.0552 (12)	0.0595 (12)	−0.0069 (10)	0.0015 (11)	−0.0013 (11)
C9	0.0750 (15)	0.0592 (13)	0.0556 (13)	−0.0098 (12)	−0.0075 (12)	0.0017 (12)
C10	0.0926 (18)	0.0598 (13)	0.0532 (13)	−0.0039 (13)	0.0102 (14)	0.0022 (12)
C11	0.0671 (14)	0.0712 (15)	0.0679 (15)	0.0016 (12)	0.0192 (13)	0.0048 (13)
C12	0.0578 (12)	0.0658 (14)	0.0663 (14)	0.0007 (11)	0.0094 (12)	−0.0008 (13)
Cl1	0.0939 (5)	0.1250 (7)	0.0821 (5)	−0.0306 (5)	−0.0317 (4)	0.0267 (5)
N1	0.0536 (10)	0.0611 (10)	0.0481 (10)	0.0027 (8)	0.0041 (9)	−0.0041 (9)
O1	0.0762 (11)	0.0904 (12)	0.0470 (8)	0.0010 (10)	−0.0033 (8)	−0.0001 (9)
O2	0.0467 (8)	0.0850 (11)	0.0717 (11)	0.0016 (8)	−0.0091 (8)	−0.0047 (10)
S1	0.0492 (3)	0.0659 (3)	0.0499 (3)	−0.0007 (2)	−0.0058 (2)	−0.0026 (3)

C1—C6	1.358 (4)	C7—N1	1.438 (3)
C1—C2	1.378 (4)	C8—C9	1.386 (3)
C1—S1	1.755 (2)	C8—H8	0.93
C2—C3	1.382 (4)	C9—C10	1.378 (4)
C2—H2	0.93	C9—Cl1	1.731 (3)
C3—C4	1.339 (5)	C10—C11	1.367 (4)
C3—H3	0.93	C10—H10	0.93
C4—C5	1.353 (6)	C11—C12	1.371 (4)
C4—H4	0.93	C11—H11	0.93
C5—C6	1.394 (5)	C12—H12	0.93
C5—H5	0.93	N1—S1	1.623 (2)
C6—H6	0.93	N1—H1N	0.876 (10)
C7—C8	1.371 (3)	O1—S1	1.4305 (17)
C7—C12	1.379 (3)	O2—S1	1.4256 (17)
C6—C1—C2	120.8 (3)	C9—C8—H8	120.7
C6—C1—S1	120.3 (2)	C10—C9—C8	120.9 (2)
C2—C1—S1	118.9 (2)	C10—C9—Cl1	120.41 (19)
C1—C2—C3	119.0 (3)	C8—C9—Cl1	118.73 (19)
C1—C2—H2	120.5	C11—C10—C9	119.3 (2)
C3—C2—H2	120.5	C11—C10—H10	120.3
C4—C3—C2	120.5 (3)	C9—C10—H10	120.3
C4—C3—H3	119.8	C10—C11—C12	120.8 (2)
C2—C3—H3	119.8	C10—C11—H11	119.6
C3—C4—C5	120.6 (4)	C12—C11—H11	119.6
C3—C4—H4	119.7	C11—C12—C7	119.6 (2)
C5—C4—H4	119.7	C11—C12—H12	120.2
C4—C5—C6	120.6 (4)	C7—C12—H12	120.2
C4—C5—H5	119.7	C7—N1—S1	122.09 (15)
C6—C5—H5	119.7	C7—N1—H1N	112.2 (16)
C1—C6—C5	118.4 (3)	S1—N1—H1N	106.4 (17)
C1—C6—H6	120.8	O2—S1—O1	119.45 (11)
C5—C6—H6	120.8	O2—S1—N1	107.89 (11)
C8—C7—C12	120.81 (19)	O1—S1—N1	104.81 (11)
C8—C7—N1	118.6 (2)	O2—S1—C1	107.00 (12)
C12—C7—N1	120.5 (2)	O1—S1—C1	108.81 (12)
C7—C8—C9	118.7 (2)	N1—S1—C1	108.50 (10)
C7—C8—H8	120.7
C6—C1—C2—C3	1.4 (4)	C10—C11—C12—C7	0.7 (4)
S1—C1—C2—C3	−177.7 (2)	C8—C7—C12—C11	−0.4 (4)
C1—C2—C3—C4	−0.4 (5)	N1—C7—C12—C11	−176.9 (2)
C2—C3—C4—C5	0.3 (7)	C8—C7—N1—S1	115.6 (2)
C3—C4—C5—C6	−1.2 (8)	C12—C7—N1—S1	−67.8 (3)
C2—C1—C6—C5	−2.2 (5)	C7—N1—S1—O2	55.5 (2)
S1—C1—C6—C5	176.8 (3)	C7—N1—S1—O1	−176.22 (17)
C4—C5—C6—C1	2.1 (8)	C7—N1—S1—C1	−60.1 (2)
C12—C7—C8—C9	−0.5 (3)	C6—C1—S1—O2	−13.9 (3)
N1—C7—C8—C9	176.1 (2)	C2—C1—S1—O2	165.1 (2)
C7—C8—C9—C10	1.2 (3)	C6—C1—S1—O1	−144.3 (3)
C7—C8—C9—Cl1	−178.94 (17)	C2—C1—S1—O1	34.8 (2)
C8—C9—C10—C11	−1.0 (4)	C6—C1—S1—N1	102.2 (3)
Cl1—C9—C10—C11	179.2 (2)	C2—C1—S1—N1	−78.7 (2)
C9—C10—C11—C12	0.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.88 (1)	2.029 (13)	2.875 (2)	162 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.88 (1)	2.029 (13)	2.875 (2)	162 (2)

Symmetry code: (i) .