2-Chloro-N-(4-meth-oxy-benzo-yl)-benzene-sulfonamide.

In the title compound, C14H12ClNO4S, the dihedral angle between the aromatic rings is 82.07 (1)° and the dihedral angle between the planes defined by the S-N-C=O fragment and the sulfonyl benzene ring is 82.46 (3)°. In the crystal, the mol-ecules are linked into C(4) chains running along [001] by strong N-H⋯O hydrogen bonds. A C-H⋯O intera-ction reinforces the [001] chains: its graph-set symbol is C(7). The chains are cross-linked into (100) sheets by further C-H⋯O inter-actions as C(6) chains along [001]. The structure also features weak π-π stacking inter-actions [centroid-centroid distances = 3.577 (1) and 3.8016 (1) Å].

Related literature

For related structures see: Gowda et al. (2010a ▶,b ▶); Suchetan et al. (2011a ▶,b ▶).

Experimental

Crystal data

C14H12ClNO4S

M = 325.76

Monoclinic,

a = 14.5293 (19) Å

b = 10.6225 (14) Å

c = 9.6918 (14) Å

β = 92.695 (5)°

V = 1494.2 (4) Å3

Z = 4

Cu Kα radiation

μ = 3.71 mm−1

T = 293 K

0.44 × 0.35 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.263, T max = 0.381

17846 measured reflections

2449 independent reflections

2295 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.163

S = 1.11

2449 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814001482/hb7189sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001482/hb7189Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001482/hb7189Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H12ClNO4S	Prism
Mr = 325.76	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Melting point: 445 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 14.5293 (19) Å	Cell parameters from 25 reflections
b = 10.6225 (14) Å	θ = 3.0–64.6°
c = 9.6918 (14) Å	µ = 3.71 mm−1
β = 92.695 (5)°	T = 293 K
V = 1494.2 (4) Å3	Prism, colourless
Z = 4	0.44 × 0.35 × 0.26 mm
F(000) = 672

Bruker APEXII CCD diffractometer	2449 independent reflections
Radiation source: fine-focus sealed tube	2295 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
phi and φ scans	θmax = 64.6°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
Tmin = 0.263, Tmax = 0.381	k = −12→12
17846 measured reflections	l = −11→9

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.109P)2 + 0.3886P] where P = (Fo2 + 2Fc2)/3
2449 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.37 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
H1	0.718 (2)	0.192 (3)	0.295 (4)	0.066 (10)*
S1	0.79503 (4)	0.19067 (5)	0.11546 (6)	0.0448 (3)
Cl1	0.90252 (7)	0.02535 (9)	0.35628 (9)	0.0882 (4)
O1	0.85786 (12)	0.27002 (19)	0.1915 (2)	0.0592 (5)
O2	0.75657 (13)	0.2343 (2)	−0.01265 (19)	0.0645 (5)
O4	0.32115 (14)	0.1078 (2)	0.5017 (3)	0.0826 (7)
C9	0.54708 (16)	0.1902 (2)	0.3736 (3)	0.0497 (6)
H9	0.5956	0.2456	0.3921	0.060*
C8	0.55277 (15)	0.1039 (2)	0.2671 (2)	0.0439 (5)
C7	0.63122 (16)	0.0964 (2)	0.1759 (2)	0.0467 (6)
N1	0.71064 (13)	0.1640 (2)	0.2183 (2)	0.0482 (5)
O3	0.62999 (14)	0.0385 (2)	0.0682 (2)	0.0705 (6)
C10	0.47035 (18)	0.1952 (3)	0.4531 (3)	0.0562 (7)
H10	0.4673	0.2543	0.5235	0.067*
C13	0.47841 (19)	0.0229 (3)	0.2399 (3)	0.0603 (7)
H13	0.4801	−0.0340	0.1671	0.072*
C1	0.84769 (15)	0.0440 (2)	0.0838 (3)	0.0485 (6)
C11	0.39843 (17)	0.1122 (3)	0.4276 (3)	0.0565 (6)
C2	0.89668 (17)	−0.0230 (3)	0.1868 (3)	0.0604 (7)
C12	0.4026 (2)	0.0265 (3)	0.3197 (4)	0.0679 (8)
H12	0.3539	−0.0287	0.3013	0.081*
C3	0.9432 (2)	−0.1334 (3)	0.1497 (5)	0.0842 (12)
H3	0.9776	−0.1787	0.2160	0.101*
C6	0.8439 (2)	0.0008 (3)	−0.0515 (3)	0.0638 (7)
H6	0.8105	0.0453	−0.1195	0.077*
C4	0.9373 (3)	−0.1740 (3)	0.0131 (5)	0.0893 (12)
H4	0.9668	−0.2481	−0.0107	0.107*
C5	0.8897 (3)	−0.1082 (4)	−0.0854 (5)	0.0851 (11)
H5	0.8877	−0.1362	−0.1765	0.102*
C14	0.3152 (3)	0.1932 (4)	0.6139 (5)	0.0940 (13)
H14A	0.3676	0.1823	0.6768	0.141*
H14B	0.2598	0.1771	0.6612	0.141*
H14C	0.3141	0.2780	0.5795	0.141*

	U11	U22	U33	U12	U13	U23
S1	0.0411 (4)	0.0523 (4)	0.0410 (4)	0.0020 (2)	0.0010 (3)	0.0046 (2)
Cl1	0.0929 (6)	0.0998 (7)	0.0690 (6)	−0.0016 (5)	−0.0274 (4)	0.0253 (4)
O1	0.0552 (10)	0.0589 (10)	0.0636 (12)	−0.0150 (8)	0.0034 (8)	−0.0062 (8)
O2	0.0623 (11)	0.0852 (13)	0.0459 (10)	0.0168 (10)	0.0013 (8)	0.0179 (9)
O4	0.0488 (11)	0.0906 (16)	0.1105 (19)	−0.0120 (10)	0.0257 (11)	−0.0087 (13)
C9	0.0382 (12)	0.0555 (14)	0.0552 (15)	−0.0069 (9)	−0.0011 (10)	−0.0066 (10)
C8	0.0404 (11)	0.0450 (12)	0.0459 (12)	−0.0027 (9)	−0.0037 (9)	0.0013 (10)
C7	0.0436 (12)	0.0541 (13)	0.0418 (13)	0.0007 (10)	−0.0048 (9)	−0.0023 (10)
N1	0.0421 (10)	0.0628 (12)	0.0394 (12)	−0.0026 (9)	−0.0010 (8)	−0.0064 (10)
O3	0.0594 (11)	0.0961 (15)	0.0557 (12)	−0.0101 (10)	0.0010 (9)	−0.0290 (11)
C10	0.0429 (13)	0.0642 (16)	0.0616 (16)	−0.0030 (10)	0.0047 (11)	−0.0110 (12)
C13	0.0529 (14)	0.0595 (15)	0.0681 (17)	−0.0110 (12)	−0.0015 (12)	−0.0141 (13)
C1	0.0368 (11)	0.0534 (13)	0.0555 (14)	−0.0019 (9)	0.0043 (10)	0.0023 (11)
C11	0.0406 (12)	0.0594 (15)	0.0697 (17)	−0.0029 (11)	0.0055 (11)	0.0053 (13)
C2	0.0396 (12)	0.0604 (16)	0.0806 (19)	−0.0003 (11)	−0.0018 (12)	0.0167 (13)
C12	0.0467 (14)	0.0664 (17)	0.091 (2)	−0.0180 (12)	0.0039 (13)	−0.0085 (15)
C3	0.0488 (15)	0.0647 (19)	0.139 (4)	0.0075 (13)	0.0061 (18)	0.030 (2)
C6	0.0598 (15)	0.0699 (17)	0.0627 (17)	−0.0006 (13)	0.0115 (13)	−0.0087 (14)
C4	0.072 (2)	0.066 (2)	0.133 (4)	0.0070 (16)	0.032 (2)	−0.012 (2)
C5	0.081 (2)	0.077 (2)	0.100 (3)	−0.0035 (18)	0.030 (2)	−0.025 (2)
C14	0.0640 (19)	0.103 (3)	0.119 (3)	0.0030 (18)	0.041 (2)	−0.016 (2)

S1—O2	1.4154 (19)	C13—C12	1.375 (4)
S1—O1	1.4227 (19)	C13—H13	0.9300
S1—N1	1.641 (2)	C1—C6	1.387 (4)
S1—C1	1.769 (3)	C1—C2	1.394 (4)
Cl1—C2	1.720 (3)	C11—C12	1.390 (5)
O4—C11	1.362 (3)	C2—C3	1.408 (5)
O4—C14	1.422 (5)	C12—H12	0.9300
C9—C10	1.385 (4)	C3—C4	1.391 (6)
C9—C8	1.386 (4)	C3—H3	0.9300
C9—H9	0.9300	C6—C5	1.383 (5)
C8—C13	1.396 (3)	C6—H6	0.9300
C8—C7	1.477 (3)	C4—C5	1.348 (6)
C7—O3	1.211 (3)	C4—H4	0.9300
C7—N1	1.404 (3)	C5—H5	0.9300
N1—H1	0.80 (4)	C14—H14A	0.9600
C10—C11	1.381 (4)	C14—H14B	0.9600
C10—H10	0.9300	C14—H14C	0.9600
O2—S1—O1	118.55 (13)	O4—C11—C10	124.3 (3)
O2—S1—N1	108.28 (11)	O4—C11—C12	116.2 (2)
O1—S1—N1	105.51 (11)	C10—C11—C12	119.6 (2)
O2—S1—C1	106.98 (13)	C1—C2—C3	118.5 (3)
O1—S1—C1	109.85 (12)	C1—C2—Cl1	122.2 (2)
N1—S1—C1	107.16 (11)	C3—C2—Cl1	119.3 (3)
C11—O4—C14	117.6 (2)	C13—C12—C11	120.4 (2)
C10—C9—C8	121.2 (2)	C13—C12—H12	119.8
C10—C9—H9	119.4	C11—C12—H12	119.8
C8—C9—H9	119.4	C4—C3—C2	119.5 (3)
C9—C8—C13	118.4 (2)	C4—C3—H3	120.2
C9—C8—C7	123.8 (2)	C2—C3—H3	120.2
C13—C8—C7	117.8 (2)	C5—C6—C1	120.3 (3)
O3—C7—N1	119.4 (2)	C5—C6—H6	119.9
O3—C7—C8	124.2 (2)	C1—C6—H6	119.9
N1—C7—C8	116.4 (2)	C5—C4—C3	121.3 (3)
C7—N1—S1	122.55 (18)	C5—C4—H4	119.4
C7—N1—H1	122 (2)	C3—C4—H4	119.4
S1—N1—H1	115 (2)	C4—C5—C6	120.1 (4)
C11—C10—C9	119.9 (2)	C4—C5—H5	119.9
C11—C10—H10	120.1	C6—C5—H5	119.9
C9—C10—H10	120.1	O4—C14—H14A	109.5
C12—C13—C8	120.6 (3)	O4—C14—H14B	109.5
C12—C13—H13	119.7	H14A—C14—H14B	109.5
C8—C13—H13	119.7	O4—C14—H14C	109.5
C6—C1—C2	120.3 (3)	H14A—C14—H14C	109.5
C6—C1—S1	117.2 (2)	H14B—C14—H14C	109.5
C2—C1—S1	122.4 (2)
C10—C9—C8—C13	1.0 (4)	N1—S1—C1—C2	−67.4 (2)
C10—C9—C8—C7	178.0 (2)	C14—O4—C11—C10	−1.0 (5)
C9—C8—C7—O3	−165.9 (3)	C14—O4—C11—C12	179.3 (3)
C13—C8—C7—O3	11.1 (4)	C9—C10—C11—O4	178.5 (3)
C9—C8—C7—N1	12.8 (3)	C9—C10—C11—C12	−1.8 (4)
C13—C8—C7—N1	−170.2 (2)	C6—C1—C2—C3	1.1 (4)
O3—C7—N1—S1	12.0 (3)	S1—C1—C2—C3	−174.5 (2)
C8—C7—N1—S1	−166.74 (17)	C6—C1—C2—Cl1	−179.3 (2)
O2—S1—N1—C7	47.2 (2)	S1—C1—C2—Cl1	5.1 (3)
O1—S1—N1—C7	175.11 (19)	C8—C13—C12—C11	0.9 (5)
C1—S1—N1—C7	−67.9 (2)	O4—C11—C12—C13	−179.3 (3)
C8—C9—C10—C11	0.8 (4)	C10—C11—C12—C13	0.9 (5)
C9—C8—C13—C12	−1.9 (4)	C1—C2—C3—C4	−1.5 (4)
C7—C8—C13—C12	−179.0 (3)	Cl1—C2—C3—C4	178.9 (3)
O2—S1—C1—C6	0.9 (2)	C2—C1—C6—C5	−0.8 (4)
O1—S1—C1—C6	−129.0 (2)	S1—C1—C6—C5	175.0 (2)
N1—S1—C1—C6	116.9 (2)	C2—C3—C4—C5	1.6 (5)
O2—S1—C1—C2	176.7 (2)	C3—C4—C5—C6	−1.3 (6)
O1—S1—C1—C2	46.8 (2)	C1—C6—C5—C4	0.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.81 (3)	2.09 (3)	2.872 (3)	172 (3)
C3—H3···O1ii	0.93	2.57	3.370 (4)	144
C9—H9···O2i	0.93	2.48	3.288 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.81 (3)	2.09 (3)	2.872 (3)	172 (3)
C3—H3⋯O1ii	0.93	2.57	3.370 (4)	144
C9—H9⋯O2i	0.93	2.48	3.288 (3)	145

Symmetry codes: (i) ; (ii) .