N-(4-Acetyl-phen-yl)-4-meth-oxy-benzene-sulfonamide.

The title compound, C15H15NO4S, was obtained by the condensation of 4-amino-aceto-phenone and 4-meth-oxy-benzene-sulfonyl chloride. The dihedral angle between the benzene rings is 86.56 (9)° and the mol-ecule has an approximate V-shaped conformation. The C atom of the meth-oxy group is roughly coplanar with its attached ring [deviation = 0.177 (3) Å], as is the methyl C atom of the acetyl group with its ring [deviation = 0.065 (2) Å]. An intra-molecular C-H⋯O inter-action generates an S(6) ring. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into [010] chains. Weak C-H⋯π inter-actions are also observed.

Related literature

For related structures, see: Li et al. (2006 ▶); Xu et al. (2005 ▶). For background to and applications of sulfonamides, see: Alsughayer et al. (2011 ▶); Dragostin et al. (2013 ▶);

Experimental

Crystal data

C15H15NO4S

M = 305.35

Monoclinic,

a = 12.8220 (3) Å

b = 8.2709 (2) Å

c = 14.6165 (4) Å

β = 112.841 (1)°

V = 1428.52 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 298 K

0.48 × 0.44 × 0.33 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.894, T max = 0.924

15571 measured reflections

4120 independent reflections

2593 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.135

S = 1.04

4120 reflections

196 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2006 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813029875/hb7153sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029875/hb7153Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813029875/hb7153Isup3.cml

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

C15H15NO4S	F(000) = 640
Mr = 305.35	Dx = 1.420 Mg m−3
Monoclinic, P21/c	Melting point = 448–449 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.8220 (3) Å	Cell parameters from 4120 reflections
b = 8.2709 (2) Å	θ = 1.7–29.9°
c = 14.6165 (4) Å	µ = 0.24 mm−1
β = 112.841 (1)°	T = 298 K
V = 1428.52 (6) Å3	Block, yellow
Z = 4	0.48 × 0.44 × 0.33 mm

Bruker APEXII CCD diffractometer	4120 independent reflections
Radiation source: sealed tube	2593 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 29.9°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
Tmin = 0.894, Tmax = 0.924	k = −11→11
15571 measured reflections	l = −20→19

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0625P)2 + 0.0913P] where P = (Fo2 + 2Fc2)/3
4120 reflections	(Δ/σ)max = 0.001
196 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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
S1	0.21179 (4)	1.00630 (5)	1.08283 (4)	0.04186 (15)
O1	0.21200 (12)	1.17413 (16)	1.10664 (11)	0.0546 (4)
O2	0.14687 (11)	0.89569 (17)	1.11408 (11)	0.0529 (4)
O3	0.48523 (14)	0.21499 (16)	1.11408 (12)	0.0624 (4)
O4	0.05688 (12)	0.98389 (16)	0.64850 (11)	0.0540 (4)
N1	0.34483 (13)	0.95337 (19)	1.13298 (12)	0.0408 (4)
C1	0.16988 (14)	0.9867 (2)	0.95362 (14)	0.0378 (4)
C2	0.22355 (15)	1.0787 (2)	0.90451 (14)	0.0418 (4)
H2A	0.2849	1.1439	0.9404	0.050*
C3	0.18492 (15)	1.0722 (2)	0.80272 (15)	0.0432 (4)
H3A	0.2209	1.1321	0.7697	0.052*
C4	0.09193 (16)	0.9760 (2)	0.74878 (14)	0.0415 (4)
C5	0.04067 (17)	0.8825 (2)	0.79829 (15)	0.0487 (5)
H5A	−0.0201	0.8161	0.7627	0.058*
C6	0.07979 (16)	0.8882 (2)	0.90017 (15)	0.0466 (5)
H6A	0.0454	0.8254	0.9333	0.056*
C7	0.38891 (14)	0.7983 (2)	1.12776 (12)	0.0353 (4)
C8	0.32855 (16)	0.6554 (2)	1.12191 (14)	0.0422 (4)
H8A	0.2549	0.6591	1.1191	0.051*
C9	0.37892 (16)	0.5091 (2)	1.12029 (15)	0.0427 (4)
H9A	0.3381	0.4144	1.1157	0.051*
C10	0.48954 (16)	0.4993 (2)	1.12535 (13)	0.0381 (4)
C11	0.54871 (16)	0.6432 (2)	1.13233 (14)	0.0422 (4)
H11A	0.6230	0.6394	1.1368	0.051*
C12	0.49943 (15)	0.7902 (2)	1.13275 (14)	0.0413 (4)
H12A	0.5400	0.8849	1.1364	0.050*
C13	0.54079 (17)	0.3380 (2)	1.12393 (14)	0.0427 (4)
C14	0.66124 (18)	0.3279 (3)	1.13447 (15)	0.0542 (5)
H14A	0.6814	0.2168	1.1316	0.081*
H14B	0.7094	0.3736	1.1970	0.081*
H14C	0.6704	0.3870	1.0815	0.081*
C15	−0.0427 (2)	0.8943 (3)	0.59083 (17)	0.0666 (6)
H15A	−0.0602	0.9117	0.5215	0.100*
H15B	−0.1050	0.9300	0.6067	0.100*
H15C	−0.0297	0.7812	0.6057	0.100*
H1N1	0.3889 (18)	1.031 (2)	1.1334 (15)	0.047 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0414 (2)	0.0396 (3)	0.0475 (3)	0.00720 (19)	0.0204 (2)	−0.00056 (19)
O1	0.0597 (9)	0.0422 (8)	0.0628 (9)	0.0125 (6)	0.0248 (7)	−0.0084 (6)
O2	0.0485 (8)	0.0588 (9)	0.0603 (9)	0.0041 (6)	0.0309 (7)	0.0070 (7)
O3	0.0769 (10)	0.0329 (7)	0.0842 (11)	−0.0013 (7)	0.0386 (9)	0.0008 (7)
O4	0.0561 (9)	0.0552 (9)	0.0464 (9)	−0.0140 (7)	0.0152 (7)	−0.0038 (6)
N1	0.0411 (8)	0.0332 (8)	0.0468 (10)	0.0015 (7)	0.0156 (7)	−0.0022 (7)
C1	0.0337 (8)	0.0337 (9)	0.0464 (10)	0.0046 (7)	0.0158 (8)	0.0028 (7)
C2	0.0365 (9)	0.0369 (10)	0.0508 (12)	−0.0058 (7)	0.0156 (8)	−0.0021 (8)
C3	0.0404 (10)	0.0378 (10)	0.0528 (12)	−0.0039 (8)	0.0196 (9)	0.0016 (8)
C4	0.0412 (9)	0.0374 (10)	0.0438 (11)	0.0011 (8)	0.0143 (8)	−0.0015 (8)
C5	0.0444 (10)	0.0437 (11)	0.0526 (12)	−0.0126 (8)	0.0130 (9)	−0.0018 (9)
C6	0.0435 (10)	0.0425 (10)	0.0552 (12)	−0.0073 (8)	0.0209 (9)	0.0039 (9)
C7	0.0381 (8)	0.0344 (9)	0.0321 (9)	0.0022 (7)	0.0121 (7)	−0.0007 (7)
C8	0.0385 (9)	0.0405 (10)	0.0496 (11)	−0.0001 (8)	0.0193 (8)	0.0004 (8)
C9	0.0455 (10)	0.0337 (9)	0.0513 (11)	−0.0035 (8)	0.0213 (9)	0.0010 (8)
C10	0.0440 (9)	0.0346 (9)	0.0356 (9)	0.0016 (7)	0.0153 (8)	0.0026 (7)
C11	0.0373 (9)	0.0411 (10)	0.0494 (11)	0.0022 (8)	0.0179 (8)	0.0020 (8)
C12	0.0391 (9)	0.0346 (9)	0.0506 (11)	−0.0030 (7)	0.0180 (8)	0.0004 (8)
C13	0.0552 (11)	0.0377 (10)	0.0356 (10)	0.0069 (8)	0.0180 (9)	0.0038 (7)
C14	0.0590 (12)	0.0497 (12)	0.0530 (13)	0.0166 (10)	0.0208 (10)	−0.0003 (9)
C15	0.0587 (14)	0.0790 (16)	0.0519 (14)	−0.0175 (12)	0.0103 (11)	−0.0074 (12)

S1—O2	1.4261 (14)	C7—C12	1.392 (2)
S1—O1	1.4308 (13)	C7—C8	1.397 (2)
S1—N1	1.6335 (16)	C8—C9	1.376 (2)
S1—C1	1.7590 (19)	C8—H8A	0.9300
O3—C13	1.218 (2)	C9—C10	1.394 (3)
O4—C4	1.358 (2)	C9—H9A	0.9300
O4—C15	1.433 (3)	C10—C11	1.394 (2)
N1—C7	1.416 (2)	C10—C13	1.491 (2)
N1—H1N1	0.85 (2)	C11—C12	1.371 (2)
C1—C6	1.381 (3)	C11—H11A	0.9300
C1—C2	1.397 (3)	C12—H12A	0.9300
C2—C3	1.375 (3)	C13—C14	1.494 (3)
C2—H2A	0.9300	C14—H14A	0.9600
C3—C4	1.395 (3)	C14—H14B	0.9600
C3—H3A	0.9300	C14—H14C	0.9600
C4—C5	1.387 (3)	C15—H15A	0.9600
C5—C6	1.375 (3)	C15—H15B	0.9600
C5—H5A	0.9300	C15—H15C	0.9600
C6—H6A	0.9300
O2—S1—O1	119.39 (9)	C9—C8—C7	119.50 (17)
O2—S1—N1	108.79 (8)	C9—C8—H8A	120.3
O1—S1—N1	104.35 (9)	C7—C8—H8A	120.3
O2—S1—C1	108.17 (9)	C8—C9—C10	121.67 (17)
O1—S1—C1	108.75 (8)	C8—C9—H9A	119.2
N1—S1—C1	106.72 (8)	C10—C9—H9A	119.2
C4—O4—C15	117.12 (16)	C11—C10—C9	117.90 (16)
C7—N1—S1	126.00 (13)	C11—C10—C13	122.34 (17)
C7—N1—H1N1	113.8 (14)	C9—C10—C13	119.76 (16)
S1—N1—H1N1	112.0 (14)	C12—C11—C10	121.26 (17)
C6—C1—C2	120.09 (18)	C12—C11—H11A	119.4
C6—C1—S1	120.10 (15)	C10—C11—H11A	119.4
C2—C1—S1	119.69 (14)	C11—C12—C7	120.25 (16)
C3—C2—C1	119.49 (17)	C11—C12—H12A	119.9
C3—C2—H2A	120.3	C7—C12—H12A	119.9
C1—C2—H2A	120.3	O3—C13—C10	120.55 (18)
C2—C3—C4	120.26 (18)	O3—C13—C14	119.98 (17)
C2—C3—H3A	119.9	C10—C13—C14	119.47 (17)
C4—C3—H3A	119.9	C13—C14—H14A	109.5
O4—C4—C5	124.41 (17)	C13—C14—H14B	109.5
O4—C4—C3	115.76 (17)	H14A—C14—H14B	109.5
C5—C4—C3	119.82 (18)	C13—C14—H14C	109.5
C6—C5—C4	119.90 (18)	H14A—C14—H14C	109.5
C6—C5—H5A	120.0	H14B—C14—H14C	109.5
C4—C5—H5A	120.0	O4—C15—H15A	109.5
C5—C6—C1	120.40 (18)	O4—C15—H15B	109.5
C5—C6—H6A	119.8	H15A—C15—H15B	109.5
C1—C6—H6A	119.8	O4—C15—H15C	109.5
C12—C7—C8	119.41 (16)	H15A—C15—H15C	109.5
C12—C7—N1	117.40 (16)	H15B—C15—H15C	109.5
C8—C7—N1	123.14 (17)
O2—S1—N1—C7	53.22 (18)	C2—C1—C6—C5	−1.4 (3)
O1—S1—N1—C7	−178.31 (15)	S1—C1—C6—C5	174.65 (15)
C1—S1—N1—C7	−63.27 (17)	S1—N1—C7—C12	151.37 (15)
O2—S1—C1—C6	5.98 (17)	S1—N1—C7—C8	−31.2 (3)
O1—S1—C1—C6	−125.08 (15)	C12—C7—C8—C9	−0.6 (3)
N1—S1—C1—C6	122.88 (15)	N1—C7—C8—C9	−177.92 (17)
O2—S1—C1—C2	−177.94 (13)	C7—C8—C9—C10	0.6 (3)
O1—S1—C1—C2	51.00 (16)	C8—C9—C10—C11	0.1 (3)
N1—S1—C1—C2	−61.03 (15)	C8—C9—C10—C13	179.65 (17)
C6—C1—C2—C3	1.0 (3)	C9—C10—C11—C12	−1.0 (3)
S1—C1—C2—C3	−175.13 (14)	C13—C10—C11—C12	179.50 (17)
C1—C2—C3—C4	0.8 (3)	C10—C11—C12—C7	1.0 (3)
C15—O4—C4—C5	2.7 (3)	C8—C7—C12—C11	−0.3 (3)
C15—O4—C4—C3	−176.22 (18)	N1—C7—C12—C11	177.24 (17)
C2—C3—C4—O4	176.85 (16)	C11—C10—C13—O3	−177.28 (18)
C2—C3—C4—C5	−2.2 (3)	C9—C10—C13—O3	3.2 (3)
O4—C4—C5—C6	−177.21 (18)	C11—C10—C13—C14	2.6 (3)
C3—C4—C5—C6	1.7 (3)	C9—C10—C13—C14	−176.96 (18)
C4—C5—C6—C1	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3i	0.85 (2)	2.05 (2)	2.896 (2)	172.3 (19)
C8—H8A···O2	0.93	2.38	3.030 (2)	127
C9—H9A···O1ii	0.93	2.53	3.459 (2)	174
C14—H14A···Cg1i	0.96	2.83	3.630 (3)	141
C14—H14C···Cg2iii	0.96	2.83	3.529 (2)	130
C15—H15C···Cg1iv	0.96	2.99	3.804 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3i	0.85 (2)	2.05 (2)	2.896 (2)	172.3 (19)
C8—H8A⋯O2	0.93	2.38	3.030 (2)	127
C9—H9A⋯O1ii	0.93	2.53	3.459 (2)	174
C14—H14A⋯Cg1i	0.96	2.83	3.630 (3)	141
C14—H14C⋯Cg2iii	0.96	2.83	3.529 (2)	130
C15—H15C⋯Cg1iv	0.96	2.99	3.804 (3)	144

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