Methyl 4-{[(4-methyl-phen-yl)sulfon-yl]amino}-benzoate.

In the mol-ecule of the title compound, C(15)H(15)NO(4)S, the dihedral angle between the two rings is 88.05 (7)°. The methyl ester group is nearly coplanar with the adjacent ring [dihedral angle = 2.81 (10)°], whereas it is oriented at 86.90 (9)° with respect to the plane of the ring attached to the -SO(2)- group. Weak intra-molecular C-H⋯O hydrogen bonding completes S(5) and S(6) ring motifs. The mol-ecules form one-dimensional polymeric C(8) chains along the [010] direction due to N-H⋯O hydrogen bonding and these chains are linked by C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For related crystal structures, see: Mustafa et al. (2011 ▶); Nan & Xing (2006 ▶); Xing & Nan (2005 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H15NO4S

M = 305.34

Monoclinic,

a = 7.9332 (2) Å

b = 8.2265 (2) Å

c = 22.7419 (5) Å

β = 92.769 (1)°

V = 1482.46 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.35 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.915, T max = 0.938

11165 measured reflections

2677 independent reflections

2234 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.113

S = 1.05

2677 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681200476X/bq2337sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200476X/bq2337Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200476X/bq2337Isup3.cml

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

C15H15NO4S	F(000) = 640
Mr = 305.34	Dx = 1.368 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2488 reflections
a = 7.9332 (2) Å	θ = 2.6–25.3°
b = 8.2265 (2) Å	µ = 0.23 mm−1
c = 22.7419 (5) Å	T = 296 K
β = 92.769 (1)°	Prism, colourless
V = 1482.46 (6) Å3	0.35 × 0.25 × 0.22 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2677 independent reflections
Radiation source: fine-focus sealed tube	2234 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 8.00 pixels mm-1	θmax = 25.3°, θmin = 2.6°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.915, Tmax = 0.938	l = −27→27
11165 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0548P)2 + 0.5778P] where P = (Fo2 + 2Fc2)/3
2677 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.28 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 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	0.44553 (6)	0.55050 (6)	0.13445 (2)	0.0511 (2)
O1	0.55975 (19)	0.43449 (19)	0.16030 (7)	0.0678 (5)
O2	0.4968 (2)	0.71630 (18)	0.12957 (7)	0.0652 (5)
O3	0.2286 (2)	−0.24936 (18)	0.00003 (8)	0.0721 (6)
O4	0.1308 (2)	−0.11198 (18)	−0.07868 (7)	0.0622 (5)
N1	0.3940 (2)	0.4952 (2)	0.06731 (7)	0.0521 (5)
C1	0.2595 (2)	0.5454 (2)	0.17369 (8)	0.0449 (6)
C2	0.2551 (3)	0.4587 (3)	0.22508 (10)	0.0659 (8)
C3	0.1124 (3)	0.4643 (3)	0.25712 (10)	0.0711 (9)
C4	−0.0272 (3)	0.5533 (3)	0.23879 (9)	0.0552 (7)
C5	−0.0206 (3)	0.6378 (3)	0.18633 (9)	0.0586 (7)
C6	0.1211 (3)	0.6352 (3)	0.15395 (9)	0.0538 (6)
C7	−0.1815 (3)	0.5595 (4)	0.27480 (11)	0.0781 (10)
C8	0.3434 (2)	0.3396 (2)	0.04751 (8)	0.0451 (6)
C9	0.3805 (3)	0.1972 (3)	0.07832 (10)	0.0588 (7)
C10	0.3323 (3)	0.0495 (2)	0.05412 (9)	0.0574 (7)
C11	0.2481 (2)	0.0400 (2)	−0.00030 (8)	0.0466 (6)
C12	0.2112 (3)	0.1827 (3)	−0.03051 (9)	0.0536 (6)
C13	0.2571 (3)	0.3307 (2)	−0.00672 (9)	0.0525 (6)
C14	0.2038 (3)	−0.1214 (3)	−0.02501 (9)	0.0520 (7)
C15	0.0800 (3)	−0.2637 (3)	−0.10630 (12)	0.0721 (9)
H1	0.39816	0.56949	0.04082	0.0625*
H2	0.34755	0.39672	0.23815	0.0791*
H3	0.11033	0.40628	0.29218	0.0853*
H5	−0.11403	0.69750	0.17272	0.0703*
H6	0.12372	0.69359	0.11898	0.0645*
H7A	−0.22071	0.66961	0.27694	0.1174*
H7B	−0.15350	0.52002	0.31379	0.1174*
H7C	−0.26853	0.49272	0.25664	0.1174*
H9	0.43730	0.20136	0.11503	0.0705*
H10	0.35718	−0.04558	0.07491	0.0688*
H12	0.15469	0.17832	−0.06728	0.0642*
H13	0.22991	0.42566	−0.02725	0.0630*
H15A	0.17843	−0.32685	−0.11387	0.1082*
H15B	0.01810	−0.24183	−0.14275	0.1082*
H15C	0.00991	−0.32322	−0.08062	0.1082*

	U11	U22	U33	U12	U13	U23
S1	0.0506 (3)	0.0488 (3)	0.0540 (3)	−0.0005 (2)	0.0037 (2)	−0.0092 (2)
O1	0.0567 (8)	0.0731 (10)	0.0721 (10)	0.0153 (7)	−0.0114 (7)	−0.0152 (8)
O2	0.0702 (9)	0.0558 (9)	0.0707 (10)	−0.0156 (7)	0.0161 (8)	−0.0158 (7)
O3	0.0901 (12)	0.0417 (9)	0.0834 (12)	−0.0012 (8)	−0.0057 (9)	0.0020 (8)
O4	0.0744 (10)	0.0548 (9)	0.0572 (9)	−0.0059 (7)	0.0018 (7)	−0.0106 (7)
N1	0.0674 (10)	0.0418 (9)	0.0478 (9)	−0.0040 (8)	0.0107 (8)	−0.0028 (7)
C1	0.0516 (10)	0.0397 (10)	0.0432 (10)	−0.0008 (8)	0.0008 (8)	−0.0022 (8)
C2	0.0750 (14)	0.0629 (14)	0.0600 (13)	0.0175 (11)	0.0052 (11)	0.0180 (11)
C3	0.0922 (17)	0.0678 (15)	0.0543 (13)	0.0031 (13)	0.0145 (12)	0.0197 (11)
C4	0.0620 (12)	0.0560 (12)	0.0480 (11)	−0.0152 (10)	0.0081 (9)	−0.0109 (9)
C5	0.0540 (11)	0.0682 (14)	0.0534 (12)	0.0063 (10)	0.0005 (9)	0.0017 (10)
C6	0.0584 (11)	0.0590 (12)	0.0439 (10)	0.0046 (10)	0.0018 (9)	0.0095 (9)
C7	0.0740 (15)	0.097 (2)	0.0652 (15)	−0.0211 (14)	0.0218 (12)	−0.0148 (14)
C8	0.0479 (10)	0.0424 (10)	0.0460 (10)	0.0000 (8)	0.0127 (8)	−0.0030 (8)
C9	0.0733 (14)	0.0487 (12)	0.0532 (12)	0.0034 (10)	−0.0090 (10)	−0.0004 (9)
C10	0.0723 (13)	0.0408 (11)	0.0583 (12)	0.0038 (9)	−0.0037 (10)	0.0050 (9)
C11	0.0484 (10)	0.0434 (10)	0.0486 (10)	0.0000 (8)	0.0082 (8)	−0.0015 (8)
C12	0.0671 (12)	0.0503 (11)	0.0431 (10)	−0.0013 (10)	0.0005 (9)	0.0009 (9)
C13	0.0678 (12)	0.0420 (10)	0.0478 (11)	0.0007 (9)	0.0039 (9)	0.0050 (9)
C14	0.0512 (11)	0.0482 (12)	0.0573 (12)	−0.0006 (9)	0.0095 (9)	−0.0038 (10)
C15	0.0735 (15)	0.0665 (15)	0.0773 (16)	−0.0151 (12)	0.0126 (12)	−0.0254 (13)

S1—O1	1.4234 (16)	C10—C11	1.380 (3)
S1—O2	1.4292 (16)	C11—C14	1.478 (3)
S1—N1	1.6264 (17)	C11—C12	1.384 (3)
S1—C1	1.7617 (17)	C12—C13	1.374 (3)
O3—C14	1.208 (3)	C2—H2	0.9300
O4—C14	1.328 (3)	C3—H3	0.9300
O4—C15	1.446 (3)	C5—H5	0.9300
N1—C8	1.409 (2)	C6—H6	0.9300
N1—H1	0.8600	C7—H7A	0.9600
C1—C6	1.380 (3)	C7—H7B	0.9600
C1—C2	1.371 (3)	C7—H7C	0.9600
C2—C3	1.376 (3)	C9—H9	0.9300
C3—C4	1.375 (3)	C10—H10	0.9300
C4—C7	1.506 (3)	C12—H12	0.9300
C4—C5	1.384 (3)	C13—H13	0.9300
C5—C6	1.374 (3)	C15—H15A	0.9600
C8—C13	1.383 (3)	C15—H15B	0.9600
C8—C9	1.389 (3)	C15—H15C	0.9600
C9—C10	1.380 (3)
O1—S1—O2	119.61 (9)	O3—C14—O4	122.5 (2)
O1—S1—N1	109.05 (9)	O3—C14—C11	124.98 (19)
O1—S1—C1	107.88 (9)	C1—C2—H2	120.00
O2—S1—N1	104.69 (9)	C3—C2—H2	120.00
O2—S1—C1	108.10 (9)	C2—C3—H3	119.00
N1—S1—C1	106.87 (8)	C4—C3—H3	119.00
C14—O4—C15	116.68 (18)	C4—C5—H5	119.00
S1—N1—C8	127.52 (13)	C6—C5—H5	119.00
S1—N1—H1	116.00	C1—C6—H6	120.00
C8—N1—H1	116.00	C5—C6—H6	120.00
S1—C1—C2	120.04 (15)	C4—C7—H7A	109.00
C2—C1—C6	120.20 (18)	C4—C7—H7B	109.00
S1—C1—C6	119.68 (15)	C4—C7—H7C	109.00
C1—C2—C3	119.3 (2)	H7A—C7—H7B	109.00
C2—C3—C4	121.9 (2)	H7A—C7—H7C	110.00
C5—C4—C7	121.2 (2)	H7B—C7—H7C	109.00
C3—C4—C5	117.7 (2)	C8—C9—H9	120.00
C3—C4—C7	121.1 (2)	C10—C9—H9	120.00
C4—C5—C6	121.4 (2)	C9—C10—H10	119.00
C1—C6—C5	119.5 (2)	C11—C10—H10	119.00
N1—C8—C13	117.01 (15)	C11—C12—H12	120.00
C9—C8—C13	119.26 (17)	C13—C12—H12	120.00
N1—C8—C9	123.70 (17)	C8—C13—H13	120.00
C8—C9—C10	119.6 (2)	C12—C13—H13	120.00
C9—C10—C11	121.35 (18)	O4—C15—H15A	109.00
C10—C11—C12	118.60 (17)	O4—C15—H15B	109.00
C12—C11—C14	122.18 (18)	O4—C15—H15C	109.00
C10—C11—C14	119.21 (16)	H15A—C15—H15B	109.00
C11—C12—C13	120.68 (19)	H15A—C15—H15C	109.00
C8—C13—C12	120.54 (17)	H15B—C15—H15C	110.00
O4—C14—C11	112.48 (19)
O1—S1—N1—C8	47.14 (18)	C2—C3—C4—C7	−179.3 (2)
O2—S1—N1—C8	176.25 (15)	C3—C4—C5—C6	−0.9 (4)
C1—S1—N1—C8	−69.23 (17)	C7—C4—C5—C6	178.7 (2)
O1—S1—C1—C2	9.46 (19)	C4—C5—C6—C1	0.6 (4)
O1—S1—C1—C6	−173.61 (16)	N1—C8—C9—C10	−177.01 (19)
O2—S1—C1—C2	−121.20 (17)	C13—C8—C9—C10	0.7 (3)
O2—S1—C1—C6	55.73 (18)	N1—C8—C13—C12	176.58 (19)
N1—S1—C1—C2	126.60 (17)	C9—C8—C13—C12	−1.2 (3)
N1—S1—C1—C6	−56.47 (18)	C8—C9—C10—C11	0.2 (3)
C15—O4—C14—O3	0.5 (3)	C9—C10—C11—C12	−0.4 (3)
C15—O4—C14—C11	−178.99 (17)	C9—C10—C11—C14	178.2 (2)
S1—N1—C8—C9	−21.7 (3)	C10—C11—C12—C13	−0.2 (3)
S1—N1—C8—C13	160.56 (16)	C14—C11—C12—C13	−178.7 (2)
S1—C1—C2—C3	175.92 (17)	C10—C11—C14—O3	3.6 (3)
C6—C1—C2—C3	−1.0 (3)	C10—C11—C14—O4	−176.90 (19)
S1—C1—C6—C5	−176.55 (17)	C12—C11—C14—O3	−177.8 (2)
C2—C1—C6—C5	0.4 (3)	C12—C11—C14—O4	1.7 (3)
C1—C2—C3—C4	0.7 (4)	C11—C12—C13—C8	1.0 (3)
C2—C3—C4—C5	0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	2.1800	2.878 (2)	138
C2—H2···O1	0.93	2.5200	2.898 (3)	105
C3—H3···O2ii	0.93	2.5500	3.431 (3)	159
C7—H7C···O1iii	0.96	2.5700	3.396 (3)	145
C9—H9···O1	0.93	2.3600	3.009 (3)	126
C10—H10···O2iv	0.93	2.5400	3.456 (2)	166
C15—H15A···O1v	0.96	2.5300	3.463 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	2.1800	2.878 (2)	138
C2—H2⋯O1	0.93	2.5200	2.898 (3)	105
C3—H3⋯O2ii	0.93	2.5500	3.431 (3)	159
C7—H7C⋯O1iii	0.96	2.5700	3.396 (3)	145
C9—H9⋯O1	0.93	2.3600	3.009 (3)	126
C10—H10⋯O2iv	0.93	2.5400	3.456 (2)	166
C15—H15A⋯O1v	0.96	2.5300	3.463 (3)	162

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