2-Chloro-N-(3-meth-oxy-benzo-yl)benzene-sulfonamide.

In the title compound, C14H12ClNO4S, the dihedral angle between the chloro- and meth-oxy-substituted benzene rings is 87.40 (1)°. In the crystal, adjacent mol-ecules form inversion-related dimers through strong N-H⋯O hydrogen bonds, generating R 2 (2)(8) loops. The dimers are further connected through two C-H⋯O inter-actions that form C(11) chains and R 2 (2)(14) loops. Aromatic π-π stacking inter-actions [centroid-centroid separation = 3.8574 (1) Å] are also observed.

Related literature

For a similar structure, see: Gowda et al. (2010 ▶)

Experimental

Crystal data

C14H12ClNO4S

M = 325.76

Triclinic,

a = 7.5731 (5) Å

b = 10.1861 (5) Å

c = 10.3636 (6) Å

α = 94.945 (4)°

β = 96.581 (5)°

γ = 110.974 (5)°

V = 734.56 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.42 mm−1

T = 293 K

0.35 × 0.28 × 0.22 mm

Data collection

Bruker APEXII diffractometer

11351 measured reflections

2584 independent reflections

2133 reflections with I > 2σ(I)

R int = 0.038

2 standard reflections every 1 reflections intensity decay: 10%

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.101

S = 1.05

2584 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2009 ▶); 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, global. DOI: 10.1107/S1600536813018291/hg5328sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018291/hg5328Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018291/hg5328Isup3.cml

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

C14H12ClNO4S	F(000) = 336
Mr = 325.76	Prism
Triclinic, P1	Dx = 1.473 Mg m−3
Hall symbol: -P 1	Melting point: 443 K
a = 7.5731 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1861 (5) Å	Cell parameters from 1029 reflections
c = 10.3636 (6) Å	θ = 2.7–25.0°
α = 94.945 (4)°	µ = 0.42 mm−1
β = 96.581 (5)°	T = 293 K
γ = 110.974 (5)°	Prism, colourless
V = 734.56 (7) Å3	0.35 × 0.28 × 0.22 mm
Z = 2

Bruker APEXII diffractometer	Rint = 0.038
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.7°
Graphite monochromator	h = −8→8
phi and ω scans	k = −12→12
11351 measured reflections	l = −12→12
2584 independent reflections	2 standard reflections every 1 reflections
2133 reflections with I > 2σ(I)	intensity decay: 10%

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0499P)2 + 0.1773P] where P = (Fo2 + 2Fc2)/3
2584 reflections	(Δ/σ)max = 0.006
195 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.30 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
HN1	0.513 (4)	0.639 (3)	0.931 (3)	0.057 (8)*
C1	0.2590 (3)	0.4163 (2)	0.67778 (18)	0.0355 (5)
C2	0.4118 (3)	0.3814 (2)	0.6470 (2)	0.0404 (5)
C3	0.4049 (4)	0.3179 (3)	0.5217 (2)	0.0514 (6)
H3	0.5072	0.2947	0.5005	0.062*
C4	0.2458 (4)	0.2894 (3)	0.4285 (2)	0.0566 (7)
H4	0.2411	0.2460	0.3448	0.068*
C5	0.0939 (4)	0.3242 (3)	0.4578 (2)	0.0547 (6)
H5	−0.0122	0.3051	0.3940	0.066*
C6	0.0999 (3)	0.3876 (2)	0.5822 (2)	0.0450 (5)
H6	−0.0025	0.4111	0.6024	0.054*
C7	0.4531 (3)	0.7563 (2)	0.8139 (2)	0.0385 (5)
C8	0.6044 (3)	0.8929 (2)	0.8800 (2)	0.0390 (5)
C9	0.6794 (3)	0.9116 (2)	1.0120 (2)	0.0402 (5)
H9	0.6398	0.8371	1.0612	0.048*
C10	0.8142 (3)	1.0429 (2)	1.0698 (2)	0.0450 (5)
C11	0.8727 (3)	1.1534 (2)	0.9965 (3)	0.0533 (6)
H11	0.9626	1.2412	1.0355	0.064*
C12	0.7984 (4)	1.1338 (3)	0.8665 (3)	0.0585 (7)
H12	0.8384	1.2087	0.8177	0.070*
C13	0.6639 (3)	1.0035 (2)	0.8062 (2)	0.0506 (6)
H13	0.6146	0.9907	0.7176	0.061*
C14	0.8344 (4)	0.9647 (3)	1.2797 (3)	0.0710 (8)
H14A	0.6997	0.9395	1.2805	0.106*
H14B	0.9025	0.9995	1.3673	0.106*
H14C	0.8580	0.8825	1.2465	0.106*
O1	0.2842 (2)	0.39742 (15)	0.92753 (14)	0.0450 (4)
O2	0.0743 (2)	0.51231 (17)	0.83161 (15)	0.0508 (4)
O3	0.3527 (2)	0.74552 (17)	0.70992 (15)	0.0526 (4)
O4	0.8980 (3)	1.07160 (17)	1.19821 (17)	0.0628 (5)
S1	0.24743 (7)	0.48701 (5)	0.83723 (5)	0.03761 (17)
N1	0.4298 (3)	0.63820 (18)	0.87817 (18)	0.0398 (4)
Cl1	0.61560 (9)	0.41609 (7)	0.75991 (6)	0.0578 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0390 (12)	0.0294 (10)	0.0326 (10)	0.0097 (9)	−0.0032 (9)	0.0000 (8)
C2	0.0387 (13)	0.0383 (12)	0.0398 (11)	0.0116 (10)	−0.0013 (9)	0.0044 (9)
C3	0.0547 (15)	0.0508 (14)	0.0481 (13)	0.0199 (12)	0.0083 (11)	0.0019 (11)
C4	0.0656 (18)	0.0565 (15)	0.0368 (12)	0.0152 (13)	−0.0003 (11)	−0.0072 (11)
C5	0.0583 (16)	0.0535 (15)	0.0409 (13)	0.0166 (13)	−0.0149 (11)	−0.0053 (11)
C6	0.0412 (13)	0.0404 (12)	0.0469 (13)	0.0134 (10)	−0.0088 (10)	0.0000 (10)
C7	0.0385 (12)	0.0381 (12)	0.0400 (11)	0.0164 (10)	0.0054 (9)	0.0027 (9)
C8	0.0383 (12)	0.0318 (11)	0.0489 (12)	0.0145 (9)	0.0096 (10)	0.0056 (9)
C9	0.0384 (12)	0.0303 (11)	0.0499 (13)	0.0110 (9)	0.0064 (10)	0.0030 (9)
C10	0.0380 (13)	0.0344 (12)	0.0598 (14)	0.0123 (10)	0.0065 (10)	−0.0022 (10)
C11	0.0426 (14)	0.0327 (12)	0.0795 (18)	0.0084 (10)	0.0126 (12)	0.0023 (12)
C12	0.0550 (16)	0.0392 (13)	0.0849 (19)	0.0141 (12)	0.0252 (14)	0.0237 (13)
C13	0.0508 (15)	0.0462 (14)	0.0584 (14)	0.0196 (12)	0.0124 (11)	0.0142 (11)
C14	0.079 (2)	0.0590 (17)	0.0580 (16)	0.0125 (15)	−0.0047 (14)	−0.0001 (13)
O1	0.0472 (9)	0.0376 (8)	0.0398 (8)	0.0055 (7)	−0.0025 (7)	0.0085 (6)
O2	0.0379 (9)	0.0558 (10)	0.0545 (9)	0.0164 (8)	0.0025 (7)	−0.0040 (8)
O3	0.0556 (10)	0.0529 (10)	0.0475 (9)	0.0212 (8)	−0.0036 (8)	0.0079 (7)
O4	0.0652 (12)	0.0421 (10)	0.0614 (11)	0.0051 (9)	−0.0064 (9)	−0.0090 (8)
S1	0.0354 (3)	0.0351 (3)	0.0362 (3)	0.0091 (2)	−0.0017 (2)	0.0003 (2)
N1	0.0388 (11)	0.0319 (10)	0.0411 (10)	0.0091 (8)	−0.0079 (8)	0.0010 (8)
Cl1	0.0433 (4)	0.0770 (5)	0.0540 (4)	0.0283 (3)	−0.0046 (3)	0.0028 (3)

C1—C2	1.388 (3)	C9—C10	1.390 (3)
C1—C6	1.394 (3)	C9—H9	0.9300
C1—S1	1.769 (2)	C10—O4	1.365 (3)
C2—C3	1.387 (3)	C10—C11	1.382 (3)
C2—Cl1	1.732 (2)	C11—C12	1.368 (4)
C3—C4	1.379 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.390 (3)
C4—C5	1.376 (4)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.380 (3)	C14—O4	1.417 (3)
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—O3	1.218 (2)	C14—H14C	0.9600
C7—N1	1.391 (3)	O1—S1	1.4337 (14)
C7—C8	1.494 (3)	O2—S1	1.4200 (16)
C8—C13	1.386 (3)	S1—N1	1.6402 (18)
C8—C9	1.389 (3)	N1—HN1	0.79 (3)
C2—C1—C6	119.67 (19)	O4—C10—C9	123.9 (2)
C2—C1—S1	123.23 (15)	C11—C10—C9	120.2 (2)
C6—C1—S1	116.98 (17)	C12—C11—C10	120.0 (2)
C3—C2—C1	119.8 (2)	C12—C11—H11	120.0
C3—C2—Cl1	117.89 (18)	C10—C11—H11	120.0
C1—C2—Cl1	122.28 (16)	C11—C12—C13	120.9 (2)
C4—C3—C2	119.8 (2)	C11—C12—H12	119.5
C4—C3—H3	120.1	C13—C12—H12	119.5
C2—C3—H3	120.1	C8—C13—C12	119.1 (2)
C5—C4—C3	120.9 (2)	C8—C13—H13	120.5
C5—C4—H4	119.5	C12—C13—H13	120.5
C3—C4—H4	119.5	O4—C14—H14A	109.5
C4—C5—C6	119.7 (2)	O4—C14—H14B	109.5
C4—C5—H5	120.2	H14A—C14—H14B	109.5
C6—C5—H5	120.2	O4—C14—H14C	109.5
C5—C6—C1	120.2 (2)	H14A—C14—H14C	109.5
C5—C6—H6	119.9	H14B—C14—H14C	109.5
C1—C6—H6	119.9	C10—O4—C14	118.15 (18)
O3—C7—N1	120.3 (2)	O2—S1—O1	119.16 (10)
O3—C7—C8	123.37 (19)	O2—S1—N1	109.37 (10)
N1—C7—C8	116.29 (18)	O1—S1—N1	104.24 (9)
C13—C8—C9	120.4 (2)	O2—S1—C1	107.73 (10)
C13—C8—C7	117.8 (2)	O1—S1—C1	108.22 (9)
C9—C8—C7	121.78 (19)	N1—S1—C1	107.61 (10)
C8—C9—C10	119.4 (2)	C7—N1—S1	123.60 (15)
C8—C9—H9	120.3	C7—N1—HN1	119.7 (19)
C10—C9—H9	120.3	S1—N1—HN1	116.2 (19)
O4—C10—C11	115.9 (2)
C6—C1—C2—C3	−0.1 (3)	O4—C10—C11—C12	179.1 (2)
S1—C1—C2—C3	175.85 (17)	C9—C10—C11—C12	−0.2 (4)
C6—C1—C2—Cl1	179.10 (16)	C10—C11—C12—C13	0.0 (4)
S1—C1—C2—Cl1	−4.9 (3)	C9—C8—C13—C12	−0.6 (3)
C1—C2—C3—C4	−0.3 (3)	C7—C8—C13—C12	177.2 (2)
Cl1—C2—C3—C4	−179.55 (18)	C11—C12—C13—C8	0.4 (4)
C2—C3—C4—C5	0.6 (4)	C11—C10—O4—C14	176.2 (2)
C3—C4—C5—C6	−0.5 (4)	C9—C10—O4—C14	−4.5 (3)
C4—C5—C6—C1	0.1 (4)	C2—C1—S1—O2	178.82 (17)
C2—C1—C6—C5	0.2 (3)	C6—C1—S1—O2	−5.11 (19)
S1—C1—C6—C5	−175.99 (18)	C2—C1—S1—O1	−51.1 (2)
O3—C7—C8—C13	−15.7 (3)	C6—C1—S1—O1	124.97 (16)
N1—C7—C8—C13	164.6 (2)	C2—C1—S1—N1	60.99 (19)
O3—C7—C8—C9	162.0 (2)	C6—C1—S1—N1	−122.94 (17)
N1—C7—C8—C9	−17.6 (3)	O3—C7—N1—S1	−11.6 (3)
C13—C8—C9—C10	0.4 (3)	C8—C7—N1—S1	167.99 (15)
C7—C8—C9—C10	−177.34 (19)	O2—S1—N1—C7	−52.2 (2)
C8—C9—C10—O4	−179.3 (2)	O1—S1—N1—C7	179.30 (18)
C8—C9—C10—C11	0.0 (3)	C1—S1—N1—C7	64.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1i	0.78 (3)	2.14 (3)	2.926 (3)	170 (3)
C5—H5···O3ii	0.93	2.53	3.417 (3)	160
C3—H3···O3iii	0.93	2.60	3.338 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O1i	0.78 (3)	2.14 (3)	2.926 (3)	170 (3)
C5—H5⋯O3ii	0.93	2.53	3.417 (3)	160
C3—H3⋯O3iii	0.93	2.60	3.338 (3)	137

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