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

In the title compound, C(14)H(15)NO(3)S, the dihedral angle between the aromatic rings is 59.39 (14)° and the C-S-N-C torsion angle is -71.4 (2)°. In the crystal, a supra-molecular chain running along the b axis with a C(4) graph set is formed via N-H⋯O hydrogen bonds.

Related literature

For the biological activity of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For some structural studies of sulfonamides, see: Khan, Akkurt et al. (2010 ▶); Khan, Sharif et al. (2010 ▶); Sharif et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H15NO3S

M = 277.34

Monoclinic, P21

a = 9.1777 (4) Å

b = 5.2179 (2) Å

c = 15.1621 (7) Å

β = 103.518 (2)°

V = 705.97 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.31 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

6858 measured reflections

2995 independent reflections

2175 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.106

S = 1.03

2995 reflections

174 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1078 Freidel pairs

Flack parameter: 0.01 (8)

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/S1600536810052633/is2644sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052633/is2644Isup2.hkl

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

C14H15NO3S	F(000) = 292
Mr = 277.34	Dx = 1.305 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2249 reflections
a = 9.1777 (4) Å	θ = 2.4–24.3°
b = 5.2179 (2) Å	µ = 0.23 mm−1
c = 15.1621 (7) Å	T = 296 K
β = 103.518 (2)°	Needle, colourless
V = 705.97 (5) Å3	0.31 × 0.10 × 0.08 mm
Z = 2

Bruker APEXII CCD diffractometer	2175 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.028
graphite	θmax = 28.3°, θmin = 4.0°
φ and ω scans	h = −12→12
6858 measured reflections	k = −5→6
2995 independent reflections	l = −20→20

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0532P)2 + 0.0074P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2995 reflections	Δρmax = 0.22 e Å−3
174 parameters	Δρmin = −0.19 e Å−3
1 restraint	Absolute structure: Flack (1983), 1078 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (8)

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
S1	0.81437 (7)	0.96578 (12)	0.72795 (4)	0.0537 (2)
O1	0.8984 (2)	0.8808 (4)	0.66620 (15)	0.0765 (8)
O2	0.8331 (2)	1.2212 (3)	0.76342 (15)	0.0703 (7)
O3	0.6677 (2)	0.8944 (4)	1.13469 (14)	0.0716 (8)
N1	0.8557 (2)	0.7730 (4)	0.81409 (15)	0.0525 (7)
C1	0.5796 (3)	0.7294 (6)	0.61403 (19)	0.0629 (10)
C2	0.4331 (3)	0.6996 (6)	0.5708 (2)	0.0701 (11)
C3	0.3249 (3)	0.8611 (6)	0.5875 (2)	0.0660 (11)
C4	0.3684 (4)	1.0479 (7)	0.6502 (3)	0.0822 (16)
C5	0.5157 (3)	1.0831 (6)	0.6953 (2)	0.0723 (11)
C6	0.6241 (3)	0.9244 (4)	0.67623 (16)	0.0475 (8)
C7	0.1637 (4)	0.8293 (9)	0.5376 (3)	0.1073 (18)
C8	0.8041 (3)	0.8134 (4)	0.89527 (17)	0.0443 (8)
C9	0.8648 (3)	1.0074 (5)	0.95370 (17)	0.0486 (8)
C10	0.8214 (3)	1.0414 (4)	1.03440 (18)	0.0520 (9)
C11	0.7174 (3)	0.8782 (5)	1.05675 (18)	0.0518 (9)
C12	0.6576 (3)	0.6828 (5)	0.9981 (2)	0.0612 (10)
C13	0.6996 (3)	0.6528 (5)	0.91731 (19)	0.0554 (9)
C14	0.7243 (5)	1.0919 (8)	1.1956 (2)	0.0991 (16)
H1	0.65090	0.61710	0.60160	0.0750*
H1A	0.91080	0.64140	0.81100	0.0630*
H2	0.40590	0.56740	0.52900	0.0840*
H4	0.29590	1.15660	0.66330	0.0990*
H5	0.54160	1.21270	0.73820	0.0870*
H7A	0.14930	0.90180	0.47800	0.1610*
H7B	0.10020	0.91560	0.57020	0.1610*
H7C	0.13890	0.65040	0.53280	0.1610*
H9	0.93550	1.11660	0.93890	0.0580*
H10	0.86230	1.17380	1.07340	0.0620*
H12	0.58850	0.57070	1.01320	0.0730*
H13	0.65700	0.52320	0.87750	0.0660*
H14A	0.70550	1.25390	1.16510	0.1490*
H14B	0.83020	1.06920	1.21830	0.1490*
H14C	0.67580	1.08790	1.24530	0.1490*

	U11	U22	U33	U12	U13	U23
S1	0.0675 (4)	0.0424 (3)	0.0518 (4)	−0.0033 (3)	0.0152 (3)	−0.0013 (3)
O1	0.0832 (13)	0.0850 (16)	0.0698 (14)	0.0004 (11)	0.0353 (12)	−0.0016 (11)
O2	0.0908 (14)	0.0416 (10)	0.0731 (13)	−0.0108 (9)	0.0080 (12)	0.0012 (10)
O3	0.0800 (13)	0.0754 (15)	0.0635 (13)	−0.0063 (10)	0.0249 (12)	−0.0036 (11)
N1	0.0632 (13)	0.0420 (12)	0.0494 (13)	0.0113 (9)	0.0075 (11)	−0.0029 (10)
C1	0.0763 (19)	0.0586 (16)	0.0544 (17)	0.0027 (15)	0.0166 (16)	−0.0142 (15)
C2	0.083 (2)	0.0731 (19)	0.0519 (18)	−0.0090 (17)	0.0109 (16)	−0.0158 (16)
C3	0.0721 (19)	0.076 (2)	0.0511 (17)	−0.0042 (16)	0.0169 (16)	0.0056 (16)
C4	0.074 (2)	0.083 (3)	0.092 (3)	0.0204 (16)	0.024 (2)	−0.010 (2)
C5	0.080 (2)	0.0585 (16)	0.076 (2)	0.0045 (16)	0.0133 (18)	−0.0241 (16)
C6	0.0703 (15)	0.0377 (14)	0.0355 (13)	0.0045 (11)	0.0147 (11)	0.0029 (10)
C7	0.071 (2)	0.158 (4)	0.090 (3)	−0.015 (2)	0.013 (2)	−0.010 (3)
C8	0.0457 (13)	0.0346 (12)	0.0471 (15)	0.0084 (11)	−0.0004 (12)	0.0002 (11)
C9	0.0503 (13)	0.0434 (16)	0.0479 (14)	−0.0063 (11)	0.0033 (12)	−0.0019 (12)
C10	0.0572 (15)	0.0453 (16)	0.0490 (16)	−0.0038 (11)	0.0032 (13)	−0.0063 (11)
C11	0.0491 (14)	0.0518 (16)	0.0515 (16)	0.0053 (11)	0.0060 (13)	0.0009 (12)
C12	0.0594 (15)	0.0503 (15)	0.074 (2)	−0.0097 (13)	0.0157 (15)	0.0007 (14)
C13	0.0566 (15)	0.0403 (14)	0.0644 (19)	−0.0071 (12)	0.0043 (14)	−0.0096 (13)
C14	0.144 (3)	0.098 (3)	0.066 (2)	−0.026 (3)	0.046 (2)	−0.019 (2)

S1—O1	1.416 (2)	C10—C11	1.379 (4)
S1—O2	1.4324 (18)	C11—C12	1.380 (4)
S1—N1	1.622 (2)	C12—C13	1.376 (4)
S1—C6	1.752 (3)	C1—H1	0.9300
O3—C11	1.365 (3)	C2—H2	0.9300
O3—C14	1.400 (4)	C4—H4	0.9300
N1—C8	1.434 (3)	C5—H5	0.9300
N1—H1A	0.8600	C7—H7A	0.9600
C1—C6	1.383 (4)	C7—H7B	0.9600
C1—C2	1.360 (4)	C7—H7C	0.9600
C2—C3	1.370 (4)	C9—H9	0.9300
C3—C7	1.505 (5)	C10—H10	0.9300
C3—C4	1.355 (5)	C12—H12	0.9300
C4—C5	1.377 (5)	C13—H13	0.9300
C5—C6	1.376 (4)	C14—H14A	0.9600
C8—C13	1.372 (4)	C14—H14B	0.9600
C8—C9	1.375 (3)	C14—H14C	0.9600
C9—C10	1.384 (4)
O2···C9	3.043 (3)	H1A···H10iv	2.3900
O2···N1i	2.975 (3)	H1A···H14Biv	2.5500
O1···H7Bii	2.6200	H2···H7C	2.5000
O1···H1	2.6400	H2···C1ix	2.8200
O2···H1Ai	2.3700	H2···C2ix	3.0300
O2···H5	2.6100	H4···H7B	2.3700
O2···H9	2.6600	H5···O2	2.6100
N1···O2iii	2.975 (3)	H7B···O1x	2.6200
N1···H10iv	2.8000	H7B···H4	2.3700
C4···C14v	3.575 (6)	H7C···H2	2.5000
C9···O2	3.043 (3)	H9···O2	2.6600
C14···C4vi	3.575 (6)	H9···C9viii	2.9600
C1···H2vii	2.8200	H10···C14	2.5100
C2···H2vii	3.0300	H10···H14A	2.2600
C3···H14Cv	2.9100	H10···H14B	2.3500
C4···H14Cv	2.9600	H10···N1viii	2.8000
C8···H10iv	3.0700	H10···C8viii	3.0700
C9···H9iv	2.9600	H10···H1Aviii	2.3900
C10···H14B	2.7700	H12···C11v	2.9400
C10···H1Aviii	3.0200	H12···C12v	3.0100
C10···H14A	2.7000	H14A···C10	2.7000
C11···H12vi	2.9400	H14A···H10	2.2600
C12···H12vi	3.0100	H14B···C10	2.7700
C14···H10	2.5100	H14B···H10	2.3500
H1···O1	2.6400	H14B···H1Aviii	2.5500
H1A···O2iii	2.3700	H14C···C3vi	2.9100
H1A···C10iv	3.0200	H14C···C4vi	2.9600
O1—S1—O2	120.23 (12)	C8—C13—C12	120.3 (2)
O1—S1—N1	106.10 (12)	C2—C1—H1	120.00
O1—S1—C6	107.78 (12)	C6—C1—H1	119.00
O2—S1—N1	106.85 (12)	C1—C2—H2	119.00
O2—S1—C6	107.59 (11)	C3—C2—H2	119.00
N1—S1—C6	107.76 (11)	C3—C4—H4	119.00
C11—O3—C14	118.0 (2)	C5—C4—H4	119.00
S1—N1—C8	122.56 (16)	C4—C5—H5	120.00
C8—N1—H1A	119.00	C6—C5—H5	120.00
S1—N1—H1A	119.00	C3—C7—H7A	109.00
C2—C1—C6	120.9 (3)	C3—C7—H7B	109.00
C1—C2—C3	121.2 (3)	C3—C7—H7C	109.00
C4—C3—C7	121.7 (3)	H7A—C7—H7B	109.00
C2—C3—C4	117.7 (3)	H7A—C7—H7C	110.00
C2—C3—C7	120.6 (3)	H7B—C7—H7C	109.00
C3—C4—C5	122.6 (3)	C8—C9—H9	120.00
C4—C5—C6	119.3 (3)	C10—C9—H9	120.00
S1—C6—C5	121.71 (19)	C9—C10—H10	120.00
C1—C6—C5	118.3 (3)	C11—C10—H10	120.00
S1—C6—C1	120.0 (2)	C11—C12—H12	120.00
C9—C8—C13	119.6 (2)	C13—C12—H12	120.00
N1—C8—C9	119.7 (2)	C8—C13—H13	120.00
N1—C8—C13	120.6 (2)	C12—C13—H13	120.00
C8—C9—C10	120.5 (2)	O3—C14—H14A	109.00
C9—C10—C11	119.8 (2)	O3—C14—H14B	110.00
O3—C11—C12	116.2 (2)	O3—C14—H14C	109.00
O3—C11—C10	124.4 (2)	H14A—C14—H14B	110.00
C10—C11—C12	119.5 (3)	H14A—C14—H14C	109.00
C11—C12—C13	120.4 (3)	H14B—C14—H14C	109.00
O1—S1—N1—C8	173.41 (19)	C1—C2—C3—C7	178.6 (3)
O2—S1—N1—C8	44.0 (2)	C7—C3—C4—C5	−178.7 (3)
C6—S1—N1—C8	−71.4 (2)	C2—C3—C4—C5	1.4 (5)
N1—S1—C6—C5	96.3 (2)	C3—C4—C5—C6	0.3 (5)
O2—S1—C6—C1	160.9 (2)	C4—C5—C6—S1	177.6 (3)
N1—S1—C6—C1	−84.2 (2)	C4—C5—C6—C1	−2.0 (4)
O1—S1—C6—C1	29.9 (2)	N1—C8—C13—C12	175.9 (2)
O2—S1—C6—C5	−18.6 (3)	C9—C8—C13—C12	−1.1 (4)
O1—S1—C6—C5	−149.7 (2)	N1—C8—C9—C10	−176.9 (2)
C14—O3—C11—C10	0.9 (4)	C13—C8—C9—C10	0.1 (4)
C14—O3—C11—C12	−179.3 (3)	C8—C9—C10—C11	0.5 (4)
S1—N1—C8—C9	−72.4 (3)	C9—C10—C11—C12	−0.1 (4)
S1—N1—C8—C13	110.6 (2)	C9—C10—C11—O3	179.7 (2)
C2—C1—C6—C5	1.9 (4)	O3—C11—C12—C13	179.3 (2)
C6—C1—C2—C3	−0.1 (5)	C10—C11—C12—C13	−0.9 (4)
C2—C1—C6—S1	−177.7 (2)	C11—C12—C13—C8	1.5 (4)
C1—C2—C3—C4	−1.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2iii	0.86	2.37	2.975 (3)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.37	2.975 (3)	128

Symmetry code: (i) .