N-(5-Chloro-2-meth-oxy-phen-yl)benzene-sulfonamide.

In the title compound, C(13)H(12)ClNO(3)S, the dihedral angle between the two aromatic rings is 73.94 (9)°. An intra-molecular C-H⋯O hydrogen bond occurs. In the crystal, inter-molecular N-H⋯O hydrogen bonds connect the mol-ecules to centrosymmetric dimers, forming an R(2) (2)(8) ring motif. The packing is consolidated by C-H⋯O hydrogen bonds and weak π-π inter-actions [centroid-centroid distances = 3.81 (3) and 3.81 (3) Å].

Related literature

For the biological properties of sulfonamide derivatives, see: Berredjem et al. (2000 ▶); Lee & Lee (2002 ▶); Soledade et al. (2006 ▶); Xiao & Timberlake (2000 ▶). For related structures, see: Aziz-ur-Rehman et al. (2010a ▶,b ▶); Khan et al. (2010 ▶); Akkurt et al. (2010 ▶).

Experimental

Crystal data

C13H12ClNO3S

M = 297.76

Triclinic,

a = 8.2201 (2) Å

b = 8.9395 (2) Å

c = 10.5544 (2) Å

α = 77.206 (1)°

β = 76.366 (1)°

γ = 66.408 (1)°

V = 683.65 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.43 mm−1

T = 296 K

0.24 × 0.16 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

12007 measured reflections

3333 independent reflections

2906 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 1.02

3333 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.27 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041206/bt5375sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041206/bt5375Isup2.hkl

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

C13H12ClNO3S	Z = 2
Mr = 297.76	F(000) = 308
Triclinic, P1	Dx = 1.446 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2201 (2) Å	Cell parameters from 6946 reflections
b = 8.9395 (2) Å	θ = 2.5–28.2°
c = 10.5544 (2) Å	µ = 0.43 mm−1
α = 77.206 (1)°	T = 296 K
β = 76.366 (1)°	Prism, colourless
γ = 66.408 (1)°	0.24 × 0.16 × 0.08 mm
V = 683.65 (3) Å3

Bruker APEXII CCD diffractometer	2906 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.023
graphite	θmax = 28.3°, θmin = 4.0°
φ and ω scans	h = −10→10
12007 measured reflections	k = −11→11
3333 independent reflections	l = −14→12

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.1401P] where P = (Fo2 + 2Fc2)/3
3333 reflections	(Δ/σ)max = 0.001
177 parameters	Δρmax = 0.35 e Å−3
1 restraint	Δρmin = −0.27 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl1	0.29733 (8)	0.24190 (8)	0.34117 (5)	0.0934 (2)
S1	0.14406 (4)	0.27960 (4)	0.88801 (3)	0.0380 (1)
O1	0.03295 (14)	0.31471 (13)	1.01239 (9)	0.0510 (3)
O2	0.13974 (14)	0.15335 (13)	0.82861 (10)	0.0506 (3)
O3	0.1709 (2)	0.71184 (16)	0.69335 (12)	0.0734 (5)
N1	0.08081 (16)	0.45288 (14)	0.78854 (10)	0.0429 (3)
C1	0.36916 (18)	0.23297 (16)	0.90100 (12)	0.0398 (4)
C2	0.5039 (2)	0.11582 (19)	0.83059 (15)	0.0521 (5)
C3	0.6805 (2)	0.0782 (2)	0.8436 (2)	0.0696 (6)
C4	0.7178 (3)	0.1563 (3)	0.9253 (2)	0.0767 (7)
C5	0.5824 (3)	0.2731 (3)	0.9938 (2)	0.0731 (7)
C6	0.4049 (2)	0.3136 (2)	0.98279 (16)	0.0557 (5)
C7	0.16189 (18)	0.47011 (17)	0.65422 (12)	0.0422 (4)
C8	0.1896 (2)	0.35789 (19)	0.57270 (13)	0.0505 (4)
C9	0.2635 (2)	0.3861 (2)	0.44138 (15)	0.0616 (5)
C10	0.3044 (3)	0.5227 (3)	0.39090 (16)	0.0756 (7)
C11	0.2737 (3)	0.6360 (3)	0.47153 (17)	0.0739 (7)
C12	0.2046 (2)	0.6098 (2)	0.60401 (14)	0.0541 (5)
C13	0.1961 (3)	0.8625 (3)	0.6504 (3)	0.0875 (9)
H1	0.058 (2)	0.5318 (19)	0.8273 (16)	0.052 (4)*
H2	0.47690	0.06350	0.77580	0.0630*
H3	0.77380	0.00000	0.79700	0.0830*
H4	0.83650	0.12960	0.93410	0.0920*
H5	0.61010	0.32540	1.04810	0.0880*
H6	0.31220	0.39270	1.02900	0.0670*
H8	0.15940	0.26520	0.60520	0.0600*
H10	0.35290	0.53940	0.30240	0.0910*
H11	0.29940	0.73070	0.43700	0.0890*
H13A	0.32050	0.84190	0.61440	0.1310*
H13B	0.16150	0.92250	0.72360	0.1310*
H13C	0.12340	0.92620	0.58390	0.1310*

	U11	U22	U33	U12	U13	U23
Cl1	0.1058 (4)	0.0954 (4)	0.0594 (3)	0.0032 (3)	−0.0179 (2)	−0.0448 (3)
S1	0.0403 (2)	0.0368 (2)	0.0370 (2)	−0.0163 (1)	0.0011 (1)	−0.0095 (1)
O1	0.0538 (6)	0.0510 (6)	0.0416 (5)	−0.0206 (5)	0.0098 (4)	−0.0100 (4)
O2	0.0566 (6)	0.0459 (5)	0.0577 (6)	−0.0253 (5)	−0.0063 (5)	−0.0146 (4)
O3	0.1093 (11)	0.0642 (8)	0.0596 (7)	−0.0505 (8)	0.0026 (7)	−0.0160 (6)
N1	0.0491 (6)	0.0385 (6)	0.0360 (5)	−0.0107 (5)	−0.0019 (4)	−0.0111 (4)
C1	0.0435 (7)	0.0381 (6)	0.0381 (6)	−0.0193 (5)	−0.0049 (5)	0.0003 (5)
C2	0.0465 (8)	0.0504 (8)	0.0515 (8)	−0.0145 (6)	−0.0008 (6)	−0.0058 (6)
C3	0.0437 (8)	0.0664 (11)	0.0793 (11)	−0.0144 (8)	0.0003 (8)	0.0052 (9)
C4	0.0524 (10)	0.0787 (13)	0.0975 (14)	−0.0378 (10)	−0.0255 (10)	0.0310 (11)
C5	0.0829 (13)	0.0731 (12)	0.0857 (13)	−0.0494 (11)	−0.0375 (11)	0.0098 (10)
C6	0.0643 (9)	0.0529 (8)	0.0591 (9)	−0.0286 (7)	−0.0153 (7)	−0.0068 (7)
C7	0.0419 (7)	0.0437 (7)	0.0351 (6)	−0.0092 (5)	−0.0058 (5)	−0.0073 (5)
C8	0.0535 (8)	0.0491 (8)	0.0420 (7)	−0.0073 (6)	−0.0100 (6)	−0.0131 (6)
C9	0.0611 (9)	0.0675 (10)	0.0397 (7)	0.0007 (8)	−0.0109 (6)	−0.0189 (7)
C10	0.0797 (12)	0.0875 (14)	0.0370 (7)	−0.0161 (10)	0.0030 (7)	−0.0062 (8)
C11	0.0871 (13)	0.0748 (12)	0.0503 (9)	−0.0341 (10)	0.0042 (8)	0.0014 (8)
C12	0.0602 (9)	0.0554 (9)	0.0442 (7)	−0.0219 (7)	−0.0022 (6)	−0.0080 (6)
C13	0.1028 (17)	0.0654 (12)	0.1064 (17)	−0.0453 (12)	−0.0112 (13)	−0.0149 (11)

Cl1—C9	1.7424 (17)	C7—C8	1.380 (2)
S1—O1	1.4296 (10)	C8—C9	1.387 (2)
S1—O2	1.4227 (12)	C9—C10	1.358 (3)
S1—N1	1.6323 (12)	C10—C11	1.375 (3)
S1—C1	1.7588 (16)	C11—C12	1.386 (2)
O3—C12	1.361 (2)	C2—H2	0.9300
O3—C13	1.404 (3)	C3—H3	0.9300
N1—C7	1.4205 (16)	C4—H4	0.9300
N1—H1	0.828 (16)	C5—H5	0.9300
C1—C2	1.380 (2)	C6—H6	0.9300
C1—C6	1.384 (2)	C8—H8	0.9300
C2—C3	1.386 (3)	C10—H10	0.9300
C3—C4	1.374 (3)	C11—H11	0.9300
C4—C5	1.370 (3)	C13—H13A	0.9600
C5—C6	1.383 (3)	C13—H13B	0.9600
C7—C12	1.391 (2)	C13—H13C	0.9600
Cl1···C6i	3.6473 (17)	C7···Cl1iii	3.6152 (17)
Cl1···C2ii	3.6292 (17)	C7···C9iii	3.520 (2)
Cl1···C7iii	3.6152 (17)	C8···C8iii	3.566 (2)
Cl1···H2ii	2.9600	C8···O2	2.9491 (17)
Cl1···H13Aiv	3.0500	C8···C9iii	3.524 (2)
S1···H8	2.9900	C9···C8iii	3.524 (2)
O1···N1v	3.0096 (15)	C9···C7iii	3.520 (2)
O1···O1v	3.0957 (15)	C13···O2xi	3.362 (3)
O1···O3v	3.1699 (16)	C3···H11iv	3.0800
O2···C13vi	3.362 (3)	C11···H13A	2.8100
O2···C4vii	3.368 (3)	C11···H13C	2.7900
O2···C8	2.9491 (17)	C13···H11	2.5800
O2···C4viii	3.382 (2)	H1···O3	2.241 (17)
O3···O1v	3.1699 (16)	H1···O1v	2.217 (16)
O3···N1	2.6284 (19)	H2···O2	2.5100
O1···H6	2.7000	H2···Cl1ii	2.9600
O1···H1v	2.217 (16)	H4···O2ix	2.5500
O2···H13Bvi	2.4800	H6···O1	2.7000
O2···H4vii	2.5500	H8···S1	2.9900
O2···H8	2.3400	H8···O2	2.3400
O2···H2	2.5100	H11···C13	2.5800
O3···H1	2.241 (17)	H11···H13A	2.3700
N1···O3	2.6284 (19)	H11···H13C	2.3800
N1···O1v	3.0096 (15)	H11···C3iv	3.0800
C1···C3viii	3.499 (2)	H13A···C11	2.8100
C2···Cl1ii	3.6292 (17)	H13A···H11	2.3700
C3···C1viii	3.499 (2)	H13A···Cl1iv	3.0500
C4···O2ix	3.368 (3)	H13B···O2xi	2.4800
C4···O2viii	3.382 (2)	H13C···C11	2.7900
C6···Cl1x	3.6473 (17)	H13C···H11	2.3800
O1—S1—O2	118.95 (7)	C10—C11—C12	120.3 (2)
O1—S1—N1	105.06 (6)	C7—C12—C11	119.51 (16)
O1—S1—C1	109.15 (7)	O3—C12—C7	114.94 (13)
O2—S1—N1	108.21 (6)	O3—C12—C11	125.55 (17)
O2—S1—C1	107.73 (7)	C1—C2—H2	121.00
N1—S1—C1	107.19 (7)	C3—C2—H2	121.00
C12—O3—C13	119.30 (17)	C2—C3—H3	120.00
S1—N1—C7	122.57 (10)	C4—C3—H3	120.00
C7—N1—H1	115.2 (11)	C3—C4—H4	120.00
S1—N1—H1	110.4 (11)	C5—C4—H4	120.00
S1—C1—C6	118.85 (11)	C4—C5—H5	120.00
S1—C1—C2	118.88 (12)	C6—C5—H5	120.00
C2—C1—C6	122.27 (16)	C1—C6—H6	121.00
C1—C2—C3	118.25 (15)	C5—C6—H6	121.00
C2—C3—C4	120.09 (18)	C7—C8—H8	121.00
C3—C4—C5	120.9 (2)	C9—C8—H8	121.00
C4—C5—C6	120.5 (2)	C9—C10—H10	120.00
C1—C6—C5	118.07 (17)	C11—C10—H10	120.00
N1—C7—C12	117.82 (12)	C10—C11—H11	120.00
N1—C7—C8	121.96 (13)	C12—C11—H11	120.00
C8—C7—C12	120.14 (12)	O3—C13—H13A	109.00
C7—C8—C9	118.69 (15)	O3—C13—H13B	109.00
Cl1—C9—C8	117.57 (13)	O3—C13—H13C	109.00
C8—C9—C10	121.73 (16)	H13A—C13—H13B	109.00
Cl1—C9—C10	120.68 (13)	H13A—C13—H13C	109.00
C9—C10—C11	119.57 (17)	H13B—C13—H13C	109.00
O1—S1—N1—C7	179.00 (12)	C1—C2—C3—C4	0.2 (3)
O2—S1—N1—C7	−52.96 (14)	C2—C3—C4—C5	−0.7 (3)
C1—S1—N1—C7	62.98 (14)	C3—C4—C5—C6	0.6 (3)
O1—S1—C1—C2	144.89 (11)	C4—C5—C6—C1	0.0 (3)
O2—S1—C1—C2	14.43 (13)	C12—C7—C8—C9	1.2 (2)
N1—S1—C1—C2	−101.83 (12)	N1—C7—C12—O3	3.1 (2)
O1—S1—C1—C6	−34.32 (13)	C8—C7—C12—O3	179.75 (16)
O2—S1—C1—C6	−164.78 (11)	C8—C7—C12—C11	0.5 (3)
N1—S1—C1—C6	78.96 (12)	N1—C7—C12—C11	−176.09 (18)
C13—O3—C12—C7	−175.04 (19)	N1—C7—C8—C9	177.65 (15)
C13—O3—C12—C11	4.1 (3)	C7—C8—C9—C10	−1.8 (3)
S1—N1—C7—C12	−135.26 (14)	C7—C8—C9—Cl1	179.83 (13)
S1—N1—C7—C8	48.2 (2)	C8—C9—C10—C11	0.6 (3)
C2—C1—C6—C5	−0.4 (2)	Cl1—C9—C10—C11	178.93 (19)
C6—C1—C2—C3	0.3 (2)	C9—C10—C11—C12	1.2 (4)
S1—C1—C2—C3	−178.87 (12)	C10—C11—C12—C7	−1.7 (3)
S1—C1—C6—C5	178.76 (14)	C10—C11—C12—O3	179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1v	0.828 (16)	2.217 (16)	3.0096 (15)	160.2 (16)
C4—H4···O2ix	0.93	2.55	3.368 (3)	147
C8—H8···O2	0.93	2.34	2.9491 (17)	123
C13—H13B···O2xi	0.96	2.48	3.362 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.828 (16)	2.217 (16)	3.0096 (15)	160.2 (16)
C4—H4⋯O2ii	0.93	2.55	3.368 (3)	147
C8—H8⋯O2	0.93	2.34	2.9491 (17)	123
C13—H13B⋯O2iii	0.96	2.48	3.362 (3)	153

Symmetry codes: (i) ; (ii) ; (iii) .