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

In the title mol-ecule, C(15)H(17)NO(3)S, the C-S-N-C(benzene) torsion angle is 81.45 (16)°, and the two aromatic rings form a dihedral angle of 45.83 (12)°. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains parallel to the b axis.

Related literature

For the biological activity of sulfonamides, see: Ozbek et al. (2007 ▶); Parari et al. (2008 ▶). For related structures, see: Mariam et al. (2009 ▶); Arshad et al. (2009 ▶); Asiri et al. (2009 ▶); Khan et al. (2010 ▶); Akkurt et al. (2010a ▶,b ▶).

Experimental

Crystal data

C15H17NO3S

M = 291.37

Monoclinic,

a = 9.3098 (5) Å

b = 9.5664 (6) Å

c = 17.1949 (10) Å

β = 104.040 (2)°

V = 1485.65 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.15 × 0.10 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

13197 measured reflections

3670 independent reflections

1963 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.157

S = 0.99

3670 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.30 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/S1600536810023287/cv2735sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023287/cv2735Isup2.hkl

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

C15H17NO3S	F(000) = 616
Mr = 291.37	Dx = 1.303 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3431 reflections
a = 9.3098 (5) Å	θ = 2.3–24.5°
b = 9.5664 (6) Å	µ = 0.22 mm−1
c = 17.1949 (10) Å	T = 296 K
β = 104.040 (2)°	Block, colourless
V = 1485.65 (15) Å3	0.15 × 0.10 × 0.06 mm
Z = 4

Bruker APEXII CCD diffractometer	1963 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.045
graphite	θmax = 28.3°, θmin = 3.1°
φ and ω scans	h = −12→10
13197 measured reflections	k = −11→12
3670 independent reflections	l = −20→22

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0842P)2] where P = (Fo2 + 2Fc2)/3
3670 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.30 e Å−3
0 restraints	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
S1	0.86267 (6)	0.81474 (6)	0.18075 (4)	0.0619 (2)
O1	0.99631 (18)	0.7591 (2)	0.16733 (12)	0.0964 (8)
O2	0.81194 (19)	0.94809 (17)	0.14864 (9)	0.0771 (7)
O3	0.57342 (18)	0.66902 (16)	0.25621 (9)	0.0675 (6)
N1	0.73281 (18)	0.70249 (17)	0.14324 (10)	0.0532 (6)
C1	0.8828 (2)	0.8200 (2)	0.28471 (13)	0.0557 (7)
C2	0.8216 (3)	0.9285 (2)	0.31844 (14)	0.0687 (9)
C3	0.8335 (3)	0.9308 (3)	0.39875 (16)	0.0899 (11)
C4	0.9055 (4)	0.8251 (4)	0.44612 (18)	0.1036 (15)
C5	0.9646 (4)	0.7163 (4)	0.4127 (2)	0.1047 (14)
C6	0.9558 (3)	0.7136 (3)	0.33214 (17)	0.0809 (10)
C7	0.7640 (3)	0.5514 (2)	0.15704 (15)	0.0723 (9)
C8	0.6825 (4)	0.4652 (3)	0.09012 (17)	0.1080 (13)
C9	0.5821 (2)	0.7500 (2)	0.12968 (11)	0.0476 (7)
C10	0.5011 (2)	0.7321 (2)	0.18716 (12)	0.0498 (7)
C11	0.3558 (2)	0.7784 (2)	0.17143 (14)	0.0633 (9)
C12	0.2933 (3)	0.8395 (2)	0.09883 (17)	0.0740 (10)
C13	0.3707 (3)	0.8566 (2)	0.04225 (15)	0.0722 (9)
C14	0.5157 (3)	0.8111 (2)	0.05732 (13)	0.0605 (8)
C15	0.5112 (3)	0.6721 (3)	0.32343 (15)	0.0878 (11)
H2	0.77210	1.00010	0.28620	0.0820*
H3	0.79260	1.00430	0.42150	0.1080*
H4	0.91440	0.82730	0.50120	0.1240*
H5	1.01110	0.64350	0.44500	0.1260*
H6	0.99860	0.64090	0.30970	0.0970*
H7A	0.86930	0.53530	0.16450	0.0870*
H7B	0.73710	0.52310	0.20580	0.0870*
H8A	0.57950	0.46310	0.09050	0.1620*
H8B	0.72140	0.37180	0.09570	0.1620*
H8C	0.69320	0.50430	0.04040	0.1620*
H11	0.30120	0.76820	0.20970	0.0760*
H12	0.19550	0.86980	0.08830	0.0890*
H13	0.32660	0.89860	−0.00640	0.0870*
H14	0.56880	0.82170	0.01840	0.0730*
H15A	0.47490	0.76430	0.32950	0.1320*
H15B	0.58550	0.64750	0.37070	0.1320*
H15C	0.43090	0.60650	0.31570	0.1320*

	U11	U22	U33	U12	U13	U23
S1	0.0444 (4)	0.0686 (4)	0.0765 (4)	−0.0128 (3)	0.0219 (3)	−0.0093 (3)
O1	0.0473 (10)	0.1239 (15)	0.1290 (16)	−0.0121 (10)	0.0426 (10)	−0.0311 (12)
O2	0.0798 (12)	0.0655 (11)	0.0836 (11)	−0.0281 (9)	0.0152 (8)	0.0088 (8)
O3	0.0664 (10)	0.0780 (11)	0.0630 (10)	0.0078 (8)	0.0252 (8)	0.0158 (7)
N1	0.0449 (10)	0.0534 (11)	0.0631 (11)	−0.0040 (8)	0.0167 (8)	−0.0081 (8)
C1	0.0362 (11)	0.0496 (12)	0.0761 (15)	−0.0024 (9)	0.0033 (10)	−0.0073 (10)
C2	0.0755 (17)	0.0528 (14)	0.0751 (16)	0.0057 (12)	0.0132 (12)	−0.0031 (11)
C3	0.111 (2)	0.0808 (19)	0.0776 (19)	0.0022 (17)	0.0224 (16)	−0.0168 (15)
C4	0.127 (3)	0.106 (3)	0.0640 (17)	−0.010 (2)	−0.0037 (17)	−0.0083 (16)
C5	0.110 (3)	0.089 (2)	0.087 (2)	0.0113 (18)	−0.0303 (18)	0.0097 (17)
C6	0.0691 (17)	0.0680 (16)	0.089 (2)	0.0152 (13)	−0.0131 (14)	−0.0081 (13)
C7	0.0600 (15)	0.0580 (15)	0.1008 (18)	0.0077 (11)	0.0233 (13)	−0.0162 (12)
C8	0.143 (3)	0.0672 (18)	0.122 (2)	−0.0313 (18)	0.048 (2)	−0.0282 (16)
C9	0.0446 (12)	0.0434 (11)	0.0553 (12)	−0.0076 (9)	0.0130 (9)	−0.0070 (9)
C10	0.0464 (12)	0.0459 (11)	0.0576 (12)	−0.0058 (9)	0.0135 (9)	−0.0012 (9)
C11	0.0455 (13)	0.0638 (14)	0.0839 (17)	−0.0052 (10)	0.0224 (11)	−0.0003 (12)
C12	0.0492 (14)	0.0662 (16)	0.099 (2)	0.0021 (11)	0.0035 (13)	0.0004 (13)
C13	0.0691 (18)	0.0655 (15)	0.0701 (16)	−0.0038 (12)	−0.0059 (13)	0.0066 (12)
C14	0.0645 (15)	0.0628 (14)	0.0537 (13)	−0.0128 (11)	0.0132 (11)	−0.0029 (10)
C15	0.093 (2)	0.110 (2)	0.0686 (17)	−0.0052 (17)	0.0353 (14)	0.0107 (14)

S1—O1	1.4226 (19)	C12—C13	1.354 (4)
S1—O2	1.4243 (17)	C13—C14	1.382 (4)
S1—N1	1.6286 (18)	C2—H2	0.9300
S1—C1	1.752 (2)	C3—H3	0.9300
O3—C10	1.356 (2)	C4—H4	0.9300
O3—C15	1.413 (3)	C5—H5	0.9300
N1—C7	1.482 (3)	C6—H6	0.9300
N1—C9	1.439 (3)	C7—H7A	0.9700
C1—C2	1.378 (3)	C7—H7B	0.9700
C1—C6	1.376 (3)	C8—H8A	0.9600
C2—C3	1.359 (4)	C8—H8B	0.9600
C3—C4	1.368 (5)	C8—H8C	0.9600
C4—C5	1.367 (5)	C11—H11	0.9300
C5—C6	1.368 (4)	C12—H12	0.9300
C7—C8	1.468 (4)	C13—H13	0.9300
C9—C10	1.392 (3)	C14—H14	0.9300
C9—C14	1.378 (3)	C15—H15A	0.9600
C10—C11	1.386 (3)	C15—H15B	0.9600
C11—C12	1.373 (4)	C15—H15C	0.9600
O1···C11i	3.336 (3)	C11···H15A	2.6800
O1···C12i	3.347 (3)	C11···H15C	2.9200
O2···C6ii	3.300 (3)	C15···H11	2.5800
O2···C14	3.113 (3)	H2···O2	2.5300
O3···N1	2.734 (2)	H2···C11v	3.0800
O3···C2	3.383 (3)	H2···H15Cv	2.4600
O3···C7	2.965 (3)	H3···H8Cviii	2.4400
O3···C1	3.152 (3)	H4···O1viii	2.8900
O1···H11i	2.7600	H6···O1	2.6900
O1···H7A	2.4400	H6···O2vi	2.5300
O1···H4iii	2.8900	H7A···O1	2.4400
O1···H12i	2.7600	H7A···C1vi	3.0600
O1···H6	2.6900	H7A···C2vi	3.0000
O2···H13iv	2.8800	H7B···O3	2.3800
O2···H15Cv	2.9100	H7B···C10	2.9300
O2···H2	2.5300	H8A···C9	2.8200
O2···H6ii	2.5300	H8A···H15Aix	2.4700
O3···H7B	2.3800	H8C···C3iii	3.0900
N1···O3	2.734 (2)	H8C···H3iii	2.4400
C1···O3	3.152 (3)	H11···O1vii	2.7600
C2···O3	3.383 (3)	H11···C15	2.5800
C6···O2vi	3.300 (3)	H11···H15A	2.2900
C6···C7	3.472 (4)	H11···H15C	2.4700
C7···C6	3.472 (4)	H12···O1vii	2.7600
C7···O3	2.965 (3)	H13···O2iv	2.8800
C11···O1vii	3.336 (3)	H14···H15Biii	2.6000
C12···O1vii	3.347 (3)	H15A···C11	2.6800
C14···O2	3.113 (3)	H15A···H11	2.2900
C1···H7Aii	3.0600	H15A···C8v	2.9600
C2···H7Aii	3.0000	H15A···H8Av	2.4700
C3···H8Cviii	3.0900	H15B···H14viii	2.6000
C8···H15Aix	2.9600	H15C···C11	2.9200
C9···H8A	2.8200	H15C···H11	2.4700
C10···H7B	2.9300	H15C···O2ix	2.9100
C11···H2ix	3.0800	H15C···H2ix	2.4600
O1—S1—O2	119.54 (11)	C4—C3—H3	120.00
O1—S1—N1	106.47 (10)	C3—C4—H4	120.00
O1—S1—C1	107.15 (11)	C5—C4—H4	120.00
O2—S1—N1	107.01 (10)	C4—C5—H5	120.00
O2—S1—C1	108.24 (10)	C6—C5—H5	120.00
N1—S1—C1	107.96 (9)	C1—C6—H6	120.00
C10—O3—C15	119.46 (18)	C5—C6—H6	120.00
S1—N1—C7	118.81 (15)	N1—C7—H7A	109.00
S1—N1—C9	117.18 (13)	N1—C7—H7B	109.00
C7—N1—C9	118.65 (18)	C8—C7—H7A	109.00
S1—C1—C2	119.88 (16)	C8—C7—H7B	109.00
S1—C1—C6	119.90 (18)	H7A—C7—H7B	108.00
C2—C1—C6	120.2 (2)	C7—C8—H8A	109.00
C1—C2—C3	120.0 (2)	C7—C8—H8B	109.00
C2—C3—C4	120.1 (3)	C7—C8—H8C	109.00
C3—C4—C5	120.1 (3)	H8A—C8—H8B	109.00
C4—C5—C6	120.6 (3)	H8A—C8—H8C	109.00
C1—C6—C5	119.1 (3)	H8B—C8—H8C	109.00
N1—C7—C8	112.2 (2)	C10—C11—H11	120.00
N1—C9—C10	121.41 (17)	C12—C11—H11	120.00
N1—C9—C14	119.11 (19)	C11—C12—H12	119.00
C10—C9—C14	119.5 (2)	C13—C12—H12	119.00
O3—C10—C9	115.92 (17)	C12—C13—H13	120.00
O3—C10—C11	124.52 (19)	C14—C13—H13	120.00
C9—C10—C11	119.56 (19)	C9—C14—H14	120.00
C10—C11—C12	119.4 (2)	C13—C14—H14	120.00
C11—C12—C13	121.5 (2)	O3—C15—H15A	109.00
C12—C13—C14	119.6 (2)	O3—C15—H15B	109.00
C9—C14—C13	120.5 (2)	O3—C15—H15C	109.00
C1—C2—H2	120.00	H15A—C15—H15B	109.00
C3—C2—H2	120.00	H15A—C15—H15C	109.00
C2—C3—H3	120.00	H15B—C15—H15C	109.00
O1—S1—N1—C7	42.39 (19)	S1—C1—C2—C3	178.2 (2)
O1—S1—N1—C9	−163.78 (15)	C6—C1—C2—C3	0.1 (4)
O2—S1—N1—C7	171.30 (16)	S1—C1—C6—C5	−177.1 (2)
O2—S1—N1—C9	−34.87 (17)	C2—C1—C6—C5	1.0 (4)
C1—S1—N1—C7	−72.39 (18)	C1—C2—C3—C4	−0.4 (4)
C1—S1—N1—C9	81.45 (16)	C2—C3—C4—C5	−0.5 (5)
O1—S1—C1—C2	144.01 (19)	C3—C4—C5—C6	1.7 (6)
O1—S1—C1—C6	−38.0 (2)	C4—C5—C6—C1	−1.9 (5)
O2—S1—C1—C2	13.9 (2)	N1—C9—C10—O3	0.7 (3)
O2—S1—C1—C6	−168.12 (19)	N1—C9—C10—C11	−179.48 (18)
N1—S1—C1—C2	−101.66 (19)	C14—C9—C10—O3	178.90 (18)
N1—S1—C1—C6	76.4 (2)	C14—C9—C10—C11	−1.2 (3)
C15—O3—C10—C9	167.2 (2)	N1—C9—C14—C13	179.41 (18)
C15—O3—C10—C11	−12.7 (3)	C10—C9—C14—C13	1.1 (3)
S1—N1—C7—C8	−148.4 (2)	O3—C10—C11—C12	−179.24 (19)
C9—N1—C7—C8	58.1 (3)	C9—C10—C11—C12	0.9 (3)
S1—N1—C9—C10	−93.0 (2)	C10—C11—C12—C13	−0.5 (3)
S1—N1—C9—C14	88.8 (2)	C11—C12—C13—C14	0.4 (3)
C7—N1—C9—C10	60.9 (3)	C12—C13—C14—C9	−0.7 (3)
C7—N1—C9—C14	−117.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.53	2.905 (3)	104
C6—H6···O2vi	0.93	2.53	3.300 (3)	140
C7—H7A···O1	0.97	2.44	2.911 (3)	109
C7—H7B···O3	0.97	2.38	2.965 (3)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.93	2.53	3.300 (3)	140

Symmetry code: (i) .