Methyl 2-benzene-sulfonamido-benzoate.

In the title compound, C(14)H(13)NO(4)S, the conformation of the C-S-N-C segment is gauche and the two benzene rings are tilted relative to each other by 85.62 (8)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring and an C-H⋯O inter-action also occurs. In the crystal, inter-molecular C-H⋯O hydrogen bonds are observed, which link the mol-ecules into [100] C(7) chains.

Related literature

For related structures, see: Khan et al. (2010 ▶); Sharif et al. (2010 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H13NO4S

M = 291.31

Triclinic,

a = 8.341 (5) Å

b = 9.115 (3) Å

c = 10.000 (5) Å

α = 84.483 (5)°

β = 80.663 (5)°

γ = 66.674 (4)°

V = 688.5 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.18 × 0.10 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.88, T max = 0.99

12401 measured reflections

3387 independent reflections

2495 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.174

S = 1.15

3387 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.59 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 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025298/hb5518sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025298/hb5518Isup2.hkl

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

C14H13NO4S	Z = 2
Mr = 291.31	F(000) = 304
Triclinic, P1	Dx = 1.405 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.341 (5) Å	Cell parameters from 4237 reflections
b = 9.115 (3) Å	θ = 2.4–26.0°
c = 10.000 (5) Å	µ = 0.25 mm−1
α = 84.483 (5)°	T = 296 K
β = 80.663 (5)°	Block, colourless
γ = 66.674 (4)°	0.18 × 0.10 × 0.07 mm
V = 688.5 (7) Å3

Bruker APEXII CCD diffractometer	3387 independent reflections
Radiation source: fine-focus sealed tube	2495 reflections with I > 2σ(I)
graphite	Rint = 0.030
phi and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→10
Tmin = 0.88, Tmax = 0.99	k = −12→9
12401 measured reflections	l = −13→12

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.1024P)2 + 0.0155P] where P = (Fo2 + 2Fc2)/3
3387 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.58 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
C1	−0.1640 (3)	0.3379 (2)	0.3275 (2)	0.0414 (4)
C2	−0.2674 (3)	0.2666 (3)	0.4062 (2)	0.0515 (5)
H2	−0.2178	0.1809	0.4653	0.062*
C3	−0.4445 (3)	0.3239 (3)	0.3958 (3)	0.0590 (6)
H3	−0.5150	0.2763	0.4479	0.071*
C4	−0.5176 (3)	0.4511 (3)	0.3090 (3)	0.0616 (6)
H4	−0.6373	0.4889	0.3023	0.074*
C5	−0.4141 (3)	0.5228 (3)	0.2317 (3)	0.0613 (6)
H5	−0.4642	0.6093	0.1735	0.074*
C6	−0.2376 (3)	0.4666 (2)	0.2406 (2)	0.0510 (5)
H6	−0.1675	0.5148	0.1886	0.061*
C7	0.1571 (2)	0.0199 (2)	0.16147 (19)	0.0399 (4)
C8	0.0860 (3)	−0.0706 (2)	0.2535 (2)	0.0477 (5)
H8	0.0362	−0.0344	0.3403	0.057*
C9	0.0893 (3)	−0.2135 (2)	0.2163 (2)	0.0510 (5)
H9	0.0415	−0.2730	0.2785	0.061*
C10	0.1620 (3)	−0.2690 (3)	0.0889 (3)	0.0550 (6)
H10	0.1649	−0.3662	0.0652	0.066*
C11	0.2308 (3)	−0.1804 (2)	−0.0039 (2)	0.0493 (5)
H11	0.2787	−0.2179	−0.0906	0.059*
C12	0.2295 (2)	−0.0359 (2)	0.0301 (2)	0.0404 (4)
C13	0.2988 (3)	0.0601 (3)	−0.0732 (2)	0.0442 (5)
C14	0.4176 (4)	0.0777 (3)	−0.3020 (2)	0.0681 (7)
H20A	0.3188	0.1702	−0.3258	0.102*
H20B	0.4699	0.0110	−0.3789	0.102*
H20C	0.5032	0.1108	−0.2751	0.102*
N1	0.1585 (2)	0.1651 (2)	0.19647 (18)	0.0490 (4)
H1	0.2175	0.2063	0.1376	0.059*
O1	0.1165 (2)	0.3981 (2)	0.31441 (17)	0.0633 (5)
O2	0.1035 (2)	0.1602 (2)	0.44859 (15)	0.0600 (4)
O3	0.3011 (2)	0.1886 (2)	−0.05568 (16)	0.0621 (5)
O4	0.3592 (2)	−0.0106 (2)	−0.19141 (16)	0.0614 (4)
S1	0.06389 (6)	0.26618 (6)	0.33289 (5)	0.0465 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0432 (10)	0.0414 (9)	0.0435 (10)	−0.0214 (8)	−0.0027 (8)	−0.0023 (8)
C2	0.0492 (12)	0.0515 (11)	0.0524 (13)	−0.0221 (9)	−0.0011 (10)	0.0075 (10)
C3	0.0478 (12)	0.0580 (13)	0.0740 (16)	−0.0288 (10)	0.0046 (11)	−0.0002 (12)
C4	0.0431 (12)	0.0542 (12)	0.0885 (18)	−0.0185 (10)	−0.0122 (12)	−0.0020 (12)
C5	0.0570 (14)	0.0441 (11)	0.0837 (18)	−0.0190 (10)	−0.0209 (13)	0.0100 (11)
C6	0.0531 (12)	0.0470 (11)	0.0590 (13)	−0.0276 (9)	−0.0066 (10)	0.0050 (10)
C7	0.0346 (9)	0.0435 (9)	0.0400 (10)	−0.0146 (8)	−0.0072 (8)	0.0077 (8)
C8	0.0433 (11)	0.0507 (11)	0.0444 (11)	−0.0166 (9)	−0.0041 (8)	0.0096 (9)
C9	0.0491 (12)	0.0477 (11)	0.0574 (13)	−0.0231 (9)	−0.0103 (10)	0.0166 (9)
C10	0.0597 (14)	0.0450 (11)	0.0636 (14)	−0.0240 (10)	−0.0126 (11)	0.0056 (10)
C11	0.0524 (12)	0.0479 (11)	0.0469 (12)	−0.0188 (9)	−0.0077 (9)	0.0010 (9)
C12	0.0335 (9)	0.0450 (10)	0.0411 (11)	−0.0146 (8)	−0.0073 (8)	0.0073 (8)
C13	0.0383 (10)	0.0541 (11)	0.0403 (11)	−0.0198 (9)	−0.0042 (8)	0.0044 (9)
C14	0.0777 (17)	0.0807 (17)	0.0449 (14)	−0.0377 (14)	0.0081 (12)	0.0060 (12)
N1	0.0516 (10)	0.0531 (10)	0.0453 (10)	−0.0284 (8)	0.0055 (8)	0.0004 (8)
O1	0.0599 (10)	0.0711 (10)	0.0758 (12)	−0.0435 (8)	−0.0025 (8)	−0.0121 (9)
O2	0.0555 (9)	0.0795 (11)	0.0438 (9)	−0.0240 (8)	−0.0135 (7)	0.0058 (8)
O3	0.0829 (12)	0.0640 (10)	0.0500 (9)	−0.0465 (9)	0.0070 (8)	0.0011 (7)
O4	0.0775 (11)	0.0636 (9)	0.0425 (9)	−0.0333 (8)	0.0086 (7)	−0.0021 (7)
S1	0.0432 (3)	0.0566 (3)	0.0448 (3)	−0.0249 (2)	−0.0046 (2)	−0.0027 (2)

C1—C2	1.382 (3)	C9—C10	1.371 (3)
C1—C6	1.383 (3)	C9—H9	0.9300
C1—S1	1.757 (2)	C10—C11	1.375 (3)
C2—C3	1.376 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.387 (3)
C3—C4	1.374 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.483 (3)
C4—C5	1.380 (3)	C13—O3	1.210 (3)
C4—H4	0.9300	C13—O4	1.327 (3)
C5—C6	1.369 (3)	C14—O4	1.440 (3)
C5—H5	0.9300	C14—H20A	0.9600
C6—H6	0.9300	C14—H20B	0.9600
C7—C8	1.395 (3)	C14—H20C	0.9600
C7—N1	1.406 (3)	N1—S1	1.6276 (18)
C7—C12	1.406 (3)	N1—H1	0.8600
C8—C9	1.377 (3)	O1—S1	1.4215 (17)
C8—H8	0.9300	O2—S1	1.4275 (17)
C2—C1—C6	120.60 (19)	C9—C10—H10	120.1
C2—C1—S1	121.10 (17)	C11—C10—H10	120.1
C6—C1—S1	118.29 (15)	C10—C11—C12	120.9 (2)
C3—C2—C1	119.1 (2)	C10—C11—H11	119.6
C3—C2—H2	120.4	C12—C11—H11	119.6
C1—C2—H2	120.4	C11—C12—C7	119.29 (18)
C4—C3—C2	120.4 (2)	C11—C12—C13	119.84 (19)
C4—C3—H3	119.8	C7—C12—C13	120.84 (18)
C2—C3—H3	119.8	O3—C13—O4	122.3 (2)
C3—C4—C5	120.2 (2)	O3—C13—C12	125.49 (19)
C3—C4—H4	119.9	O4—C13—C12	112.25 (18)
C5—C4—H4	119.9	O4—C14—H20A	109.5
C6—C5—C4	120.0 (2)	O4—C14—H20B	109.5
C6—C5—H5	120.0	H20A—C14—H20B	109.5
C4—C5—H5	120.0	O4—C14—H20C	109.5
C5—C6—C1	119.7 (2)	H20A—C14—H20C	109.5
C5—C6—H6	120.2	H20B—C14—H20C	109.5
C1—C6—H6	120.2	C7—N1—S1	129.02 (15)
C8—C7—N1	121.83 (18)	C7—N1—H1	115.5
C8—C7—C12	118.94 (19)	S1—N1—H1	115.5
N1—C7—C12	119.23 (17)	C13—O4—C14	116.87 (18)
C9—C8—C7	120.3 (2)	O1—S1—O2	120.11 (11)
C9—C8—H8	119.9	O1—S1—N1	103.89 (10)
C7—C8—H8	119.9	O2—S1—N1	108.85 (10)
C10—C9—C8	120.8 (2)	O1—S1—C1	108.53 (10)
C10—C9—H9	119.6	O2—S1—C1	108.40 (10)
C8—C9—H9	119.6	N1—S1—C1	106.20 (9)
C9—C10—C11	119.8 (2)
C6—C1—C2—C3	0.8 (3)	N1—C7—C12—C13	−3.0 (3)
S1—C1—C2—C3	−178.17 (16)	C11—C12—C13—O3	178.5 (2)
C1—C2—C3—C4	−0.4 (3)	C7—C12—C13—O3	0.5 (3)
C2—C3—C4—C5	−0.2 (4)	C11—C12—C13—O4	−1.0 (3)
C3—C4—C5—C6	0.5 (4)	C7—C12—C13—O4	−179.01 (17)
C4—C5—C6—C1	0.0 (3)	C8—C7—N1—S1	−8.2 (3)
C2—C1—C6—C5	−0.6 (3)	C12—C7—N1—S1	171.85 (15)
S1—C1—C6—C5	178.41 (17)	O3—C13—O4—C14	−4.0 (3)
N1—C7—C8—C9	−179.05 (18)	C12—C13—O4—C14	175.53 (19)
C12—C7—C8—C9	0.9 (3)	C7—N1—S1—O1	177.77 (18)
C7—C8—C9—C10	0.0 (3)	C7—N1—S1—O2	48.7 (2)
C8—C9—C10—C11	−0.8 (3)	C7—N1—S1—C1	−67.8 (2)
C9—C10—C11—C12	0.8 (3)	C2—C1—S1—O1	−145.97 (17)
C10—C11—C12—C7	0.1 (3)	C6—C1—S1—O1	35.01 (19)
C10—C11—C12—C13	−177.87 (19)	C2—C1—S1—O2	−14.0 (2)
C8—C7—C12—C11	−0.9 (3)	C6—C1—S1—O2	167.02 (16)
N1—C7—C12—C11	179.00 (17)	C2—C1—S1—N1	102.86 (19)
C8—C7—C12—C13	177.03 (18)	C6—C1—S1—N1	−76.16 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2	0.93	2.45	3.062 (3)	124
N1—H1···O3	0.86	1.94	2.635 (3)	136
C8—H8···O2i	0.93	2.63	3.326 (3)	132
C4—H4···O1ii	0.93	2.48	3.265 (3)	142

Table 1

Selected torsion angles (°)

C7—N1—S1—C1

−67.8 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2	0.93	2.45	3.062 (3)	124
N1—H1⋯O3	0.86	1.94	2.635 (3)	136
C8—H8⋯O2i	0.93	2.63	3.326 (3)	132
C4—H4⋯O1ii	0.93	2.48	3.265 (3)	142

Symmetry codes: (i) ; (ii) .