N-(2-Meth-oxy-phen-yl)-4-methyl-benzene-sulfonamide.

In the title compound, C(14)H(15)NO(3)S, the geometry around the S atom of the SO(2) group is distorted tetra-hedral. The meth-oxy- and methyl-substituted aromatic rings are oriented at a dihedral angle of 71.39 (9)°. Inter-molecular N-H⋯O hydrogen bonds form inversion dimers, which stabilize the crystal structure.

Related literature

For the anti­microbial activity of sulfonamide compounds, see: Gao & Pederson (2005 ▶). For a related thia­zine mol­ecule, see: Arshad et al. (2010 ▶). For a related structure, see: Aziz-ur-Rehman et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H15NO3S

M = 277.33

Orthorhombic,

a = 12.7395 (9) Å

b = 11.4906 (6) Å

c = 18.6968 (10) Å

V = 2736.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.42 × 0.33 × 0.21 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.906, T max = 0.951

13798 measured reflections

3376 independent reflections

1313 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.143

S = 0.91

3376 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.28 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042984/sj5047sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042984/sj5047Isup2.hkl

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

C14H15NO3S	F(000) = 1168
Mr = 277.33	Dx = 1.346 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1013 reflections
a = 12.7395 (9) Å	θ = 3.2–19.2°
b = 11.4906 (6) Å	µ = 0.24 mm−1
c = 18.6968 (10) Å	T = 296 K
V = 2736.9 (3) Å3	Needle, light brown
Z = 8	0.42 × 0.33 × 0.21 mm

Bruker Kappa APEXII CCD diffractometer	3376 independent reflections
Radiation source: fine-focus sealed tube	1313 reflections with I > 2σ(I)
graphite	Rint = 0.086
φ and ω scans	θmax = 28.3°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −16→10
Tmin = 0.906, Tmax = 0.951	k = −11→15
13798 measured reflections	l = −24→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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.0552P)2] where P = (Fo2 + 2Fc2)/3
3376 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.28 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
S1	0.51740 (7)	0.61649 (6)	0.39096 (4)	0.0571 (3)
O1	0.60405 (18)	0.61039 (18)	0.34278 (11)	0.0706 (7)
N1	0.55946 (19)	0.6656 (2)	0.46723 (12)	0.0529 (7)
C1	0.4303 (2)	0.7199 (2)	0.35541 (14)	0.0465 (7)
O2	0.46120 (19)	0.51265 (17)	0.40827 (11)	0.0751 (7)
C2	0.4619 (3)	0.7899 (3)	0.30004 (16)	0.0584 (8)
H2	0.5298	0.7842	0.2822	0.070*
O3	0.49484 (18)	0.80720 (18)	0.56921 (11)	0.0662 (6)
C3	0.3924 (3)	0.8688 (3)	0.27103 (16)	0.0607 (9)
H3	0.4146	0.9162	0.2337	0.073*
C4	0.2908 (3)	0.8796 (2)	0.29578 (15)	0.0510 (8)
C5	0.2613 (3)	0.8091 (3)	0.35213 (17)	0.0598 (9)
H5	0.1935	0.8150	0.3703	0.072*
H1N	0.5306	0.6270	0.4999	0.072*
C6	0.3298 (3)	0.7303 (3)	0.38188 (16)	0.0610 (9)
H6	0.3082	0.6839	0.4199	0.073*
C7	0.6101 (2)	0.7748 (2)	0.47481 (15)	0.0481 (8)
C8	0.5756 (2)	0.8488 (2)	0.52917 (16)	0.0491 (8)
C9	0.6239 (3)	0.9550 (3)	0.53963 (18)	0.0650 (9)
H9	0.6006	1.0047	0.5755	0.078*
C10	0.7065 (3)	0.9868 (3)	0.4967 (2)	0.0742 (11)
H10	0.7391	1.0583	0.5038	0.089*
C11	0.7412 (3)	0.9152 (3)	0.4440 (2)	0.0766 (11)
H11	0.7969	0.9380	0.4151	0.092*
C12	0.6934 (3)	0.8076 (3)	0.43331 (16)	0.0629 (9)
H12	0.7182	0.7579	0.3979	0.075*
C13	0.2160 (3)	0.9656 (3)	0.26372 (17)	0.0697 (10)
H13A	0.2137	0.9552	0.2128	0.105*
H13B	0.2391	1.0432	0.2745	0.105*
H13C	0.1472	0.9536	0.2833	0.105*
C14	0.4637 (3)	0.8720 (3)	0.63051 (18)	0.0889 (12)
H14A	0.4396	0.9476	0.6159	0.133*
H14B	0.5224	0.8804	0.6623	0.133*
H14C	0.4079	0.8318	0.6547	0.133*

	U11	U22	U33	U12	U13	U23
S1	0.0728 (6)	0.0410 (5)	0.0575 (5)	0.0023 (4)	−0.0082 (5)	−0.0047 (4)
O1	0.0764 (17)	0.0696 (16)	0.0659 (14)	0.0201 (12)	0.0028 (13)	−0.0123 (12)
N1	0.0685 (19)	0.0410 (14)	0.0491 (14)	−0.0108 (13)	−0.0068 (13)	0.0069 (12)
C1	0.057 (2)	0.0393 (17)	0.0436 (16)	−0.0066 (15)	0.0000 (15)	−0.0013 (14)
O2	0.104 (2)	0.0370 (12)	0.0845 (16)	−0.0171 (12)	−0.0261 (14)	0.0047 (11)
C2	0.051 (2)	0.064 (2)	0.0603 (19)	0.0033 (17)	0.0091 (17)	0.0070 (17)
O3	0.0647 (17)	0.0638 (14)	0.0700 (14)	−0.0036 (12)	0.0084 (12)	−0.0086 (12)
C3	0.067 (2)	0.064 (2)	0.0515 (19)	0.0029 (19)	0.0090 (18)	0.0179 (17)
C4	0.056 (2)	0.0500 (19)	0.0469 (18)	0.0010 (16)	−0.0005 (16)	−0.0061 (16)
C5	0.051 (2)	0.063 (2)	0.065 (2)	−0.0016 (17)	0.0114 (17)	0.0007 (18)
C6	0.070 (3)	0.057 (2)	0.0552 (19)	−0.0038 (18)	0.0124 (19)	0.0129 (17)
C7	0.052 (2)	0.0433 (18)	0.0492 (18)	−0.0005 (16)	−0.0084 (16)	0.0078 (15)
C8	0.047 (2)	0.046 (2)	0.0543 (18)	−0.0001 (16)	−0.0065 (16)	0.0053 (15)
C9	0.078 (3)	0.050 (2)	0.066 (2)	−0.007 (2)	−0.014 (2)	−0.0039 (18)
C10	0.084 (3)	0.060 (2)	0.079 (2)	−0.024 (2)	−0.022 (2)	0.010 (2)
C11	0.072 (3)	0.086 (3)	0.072 (3)	−0.028 (2)	−0.007 (2)	0.020 (2)
C12	0.065 (2)	0.069 (2)	0.055 (2)	−0.0093 (19)	−0.0024 (18)	0.0010 (18)
C13	0.068 (3)	0.075 (2)	0.066 (2)	0.015 (2)	0.0018 (19)	0.0041 (18)
C14	0.098 (3)	0.100 (3)	0.069 (2)	0.005 (2)	0.012 (2)	−0.011 (2)

S1—O1	1.426 (2)	C6—H6	0.9300
S1—O2	1.429 (2)	C7—C12	1.368 (4)
S1—N1	1.625 (2)	C7—C8	1.396 (4)
S1—C1	1.756 (3)	C8—C9	1.381 (4)
N1—C7	1.418 (3)	C9—C10	1.373 (5)
N1—H1N	0.8394	C9—H9	0.9300
C1—C2	1.371 (4)	C10—C11	1.357 (5)
C1—C6	1.378 (4)	C10—H10	0.9300
C2—C3	1.378 (4)	C11—C12	1.393 (4)
C2—H2	0.9300	C11—H11	0.9300
O3—C8	1.359 (3)	C12—H12	0.9300
O3—C14	1.424 (3)	C13—H13A	0.9600
C3—C4	1.379 (4)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.382 (4)	C14—H14A	0.9600
C4—C13	1.498 (4)	C14—H14B	0.9600
C5—C6	1.375 (4)	C14—H14C	0.9600
C5—H5	0.9300
O1—S1—O2	119.32 (14)	C12—C7—N1	122.7 (3)
O1—S1—N1	108.43 (13)	C8—C7—N1	117.9 (3)
O2—S1—N1	104.86 (12)	O3—C8—C9	124.8 (3)
O1—S1—C1	106.45 (14)	O3—C8—C7	115.1 (3)
O2—S1—C1	109.52 (15)	C9—C8—C7	120.1 (3)
N1—S1—C1	107.79 (13)	C10—C9—C8	119.6 (3)
C7—N1—S1	123.03 (19)	C10—C9—H9	120.2
C7—N1—H1N	126.5	C8—C9—H9	120.2
S1—N1—H1N	108.1	C11—C10—C9	120.9 (3)
C2—C1—C6	119.5 (3)	C11—C10—H10	119.6
C2—C1—S1	119.8 (3)	C9—C10—H10	119.6
C6—C1—S1	120.6 (2)	C10—C11—C12	120.0 (4)
C1—C2—C3	119.7 (3)	C10—C11—H11	120.0
C1—C2—H2	120.2	C12—C11—H11	120.0
C3—C2—H2	120.2	C7—C12—C11	120.1 (3)
C8—O3—C14	118.1 (3)	C7—C12—H12	119.9
C2—C3—C4	122.0 (3)	C11—C12—H12	119.9
C2—C3—H3	119.0	C4—C13—H13A	109.5
C4—C3—H3	119.0	C4—C13—H13B	109.5
C3—C4—C5	117.3 (3)	H13A—C13—H13B	109.5
C3—C4—C13	121.4 (3)	C4—C13—H13C	109.5
C5—C4—C13	121.2 (3)	H13A—C13—H13C	109.5
C6—C5—C4	121.4 (3)	H13B—C13—H13C	109.5
C6—C5—H5	119.3	O3—C14—H14A	109.5
C4—C5—H5	119.3	O3—C14—H14B	109.5
C5—C6—C1	120.1 (3)	H14A—C14—H14B	109.5
C5—C6—H6	120.0	O3—C14—H14C	109.5
C1—C6—H6	120.0	H14A—C14—H14C	109.5
C12—C7—C8	119.3 (3)	H14B—C14—H14C	109.5
O1—S1—N1—C7	58.3 (3)	C2—C1—C6—C5	1.0 (5)
O2—S1—N1—C7	−173.2 (2)	S1—C1—C6—C5	−178.0 (2)
C1—S1—N1—C7	−56.5 (3)	S1—N1—C7—C12	−51.4 (4)
O1—S1—C1—C2	−11.4 (3)	S1—N1—C7—C8	131.6 (2)
O2—S1—C1—C2	−141.7 (2)	C14—O3—C8—C9	−6.2 (4)
N1—S1—C1—C2	104.7 (2)	C14—O3—C8—C7	173.0 (3)
O1—S1—C1—C6	167.6 (2)	C12—C7—C8—O3	−177.7 (3)
O2—S1—C1—C6	37.3 (3)	N1—C7—C8—O3	−0.6 (4)
N1—S1—C1—C6	−76.3 (3)	C12—C7—C8—C9	1.5 (4)
C6—C1—C2—C3	−0.7 (4)	N1—C7—C8—C9	178.6 (3)
S1—C1—C2—C3	178.3 (2)	O3—C8—C9—C10	178.5 (3)
C1—C2—C3—C4	−0.3 (5)	C7—C8—C9—C10	−0.6 (5)
C2—C3—C4—C5	1.0 (5)	C8—C9—C10—C11	0.1 (5)
C2—C3—C4—C13	−179.9 (3)	C9—C10—C11—C12	−0.5 (6)
C3—C4—C5—C6	−0.7 (5)	C8—C7—C12—C11	−1.8 (5)
C13—C4—C5—C6	−179.8 (3)	N1—C7—C12—C11	−178.9 (3)
C4—C5—C6—C1	−0.3 (5)	C10—C11—C12—C7	1.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.84	2.35	3.112 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.84	2.35	3.112 (3)	151

Symmetry code: (i) .