Methyl 2-(p-toluene-sulfonamido)benzoate.

The title compound, C(15)H(15)NO(4)S, was prepared by simple condensation of methyl 2-amino-benzoate and 4-methyl-benzene-sulfonyl chloride. The dihedral angle between the benzene rings is 84.36 (6)°. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen-bonding inter-action involving the carbonyl group as acceptor, generating an S(6) graph-set motif.

Related literature

For background information on sulfonamide derivatives and their properties, see: Sheppard et al. (2006 ▶). For similar structures, see: Schultz et al. (2001 ▶); Krishnaiah et al. (1995 ▶); Arshad, Khan, Shafiq et al. (2009 ▶); Arshad, Khan, Akkurt et al. (2009 ▶); Xiong et al. (2007 ▶).

Experimental

Crystal data

C15H15NO4S

M = 305.34

Monoclinic,

a = 15.0129 (13) Å

b = 8.3593 (7) Å

c = 11.9664 (11) Å

β = 96.854 (2)°

V = 1491.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 295 K

0.24 × 0.16 × 0.14 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.947, T max = 0.968

7663 measured reflections

2639 independent reflections

2230 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.102

S = 1.04

2639 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810000814/bh2263sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000814/bh2263Isup2.hkl

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

C15H15NO4S	F(000) = 640
Mr = 305.34	Dx = 1.360 Mg m−3
Monoclinic, P21/c	Melting point: 380 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.0129 (13) Å	Cell parameters from 3425 reflections
b = 8.3593 (7) Å	θ = 2.3–27.0°
c = 11.9664 (11) Å	µ = 0.23 mm−1
β = 96.854 (2)°	T = 295 K
V = 1491.0 (2) Å3	Block, colourless
Z = 4	0.24 × 0.16 × 0.14 mm

Bruker APEXII area-detector diffractometer	2639 independent reflections
Radiation source: fine-focus sealed tube	2230 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 25.1°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −16→17
Tmin = 0.947, Tmax = 0.968	k = −9→9
7663 measured reflections	l = −14→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.3683P] where P = (Fo2 + 2Fc2)/3
2639 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.78611 (3)	0.16418 (5)	0.77097 (4)	0.04976 (17)
O1	0.56582 (10)	0.0349 (2)	0.36179 (12)	0.0866 (5)
O2	0.61287 (10)	0.2115 (2)	0.49515 (14)	0.0784 (4)
O3	0.80078 (9)	0.05619 (17)	0.86305 (10)	0.0642 (4)
O4	0.76453 (10)	0.32689 (16)	0.79146 (12)	0.0677 (4)
N1	0.70193 (9)	0.10160 (18)	0.68303 (13)	0.0536 (4)
H1	0.6798	0.1762	0.6367	0.082 (7)*
C1	0.52814 (17)	0.1643 (4)	0.2920 (2)	0.1100 (11)
H1A	0.4763	0.2057	0.3221	0.165*
H1B	0.5111	0.1258	0.2169	0.165*
H1C	0.5720	0.2477	0.2906	0.165*
C2	0.60786 (12)	0.0751 (3)	0.46213 (17)	0.0623 (5)
C3	0.64536 (11)	−0.0668 (2)	0.52490 (15)	0.0524 (4)
C4	0.69256 (10)	−0.0513 (2)	0.63324 (14)	0.0474 (4)
C5	0.72532 (13)	−0.1874 (2)	0.68995 (18)	0.0604 (5)
H5	0.7568	−0.1781	0.7615	0.072*
C6	0.71195 (15)	−0.3359 (2)	0.6419 (2)	0.0748 (6)
H6	0.7343	−0.4261	0.6812	0.090*
C7	0.66594 (16)	−0.3525 (3)	0.5364 (2)	0.0810 (7)
H7	0.6571	−0.4534	0.5042	0.097*
C8	0.63345 (15)	−0.2203 (3)	0.47946 (19)	0.0716 (6)
H8	0.6023	−0.2324	0.4080	0.086*
C9	0.88094 (11)	0.16066 (19)	0.69848 (13)	0.0436 (4)
C10	0.88227 (13)	0.2541 (2)	0.60377 (15)	0.0556 (5)
H10	0.8323	0.3146	0.5766	0.067*
C11	0.95774 (14)	0.2569 (3)	0.55021 (16)	0.0626 (5)
H11	0.9585	0.3201	0.4864	0.075*
C12	1.03322 (12)	0.1678 (2)	0.58876 (16)	0.0581 (5)
C13	1.03009 (13)	0.0749 (2)	0.68292 (17)	0.0623 (5)
H13	1.0800	0.0144	0.7101	0.075*
C14	0.95457 (12)	0.0694 (2)	0.73804 (15)	0.0541 (4)
H14	0.9533	0.0048	0.8011	0.065*
C15	1.11567 (15)	0.1736 (3)	0.5291 (2)	0.0877 (8)
H15A	1.1455	0.2744	0.5438	0.132*
H15B	1.0988	0.1620	0.4495	0.132*
H15C	1.1555	0.0883	0.5557	0.132*

	U11	U22	U33	U12	U13	U23
S1	0.0530 (3)	0.0496 (3)	0.0468 (3)	−0.00029 (19)	0.00665 (19)	−0.00452 (18)
O1	0.0675 (9)	0.1255 (14)	0.0618 (9)	−0.0107 (9)	−0.0128 (7)	0.0207 (9)
O2	0.0743 (10)	0.0717 (10)	0.0861 (11)	0.0118 (8)	−0.0036 (8)	0.0221 (9)
O3	0.0755 (9)	0.0734 (9)	0.0435 (7)	−0.0095 (7)	0.0067 (6)	0.0063 (6)
O4	0.0695 (9)	0.0557 (8)	0.0801 (9)	0.0029 (6)	0.0177 (7)	−0.0180 (7)
N1	0.0498 (8)	0.0470 (8)	0.0620 (9)	0.0048 (7)	−0.0016 (7)	−0.0006 (7)
C1	0.0695 (15)	0.170 (3)	0.0853 (17)	−0.0053 (16)	−0.0123 (13)	0.0621 (19)
C2	0.0391 (9)	0.0881 (16)	0.0591 (12)	−0.0040 (10)	0.0037 (8)	0.0139 (11)
C3	0.0395 (9)	0.0634 (11)	0.0542 (10)	−0.0029 (8)	0.0053 (7)	0.0010 (9)
C4	0.0382 (8)	0.0497 (10)	0.0549 (10)	0.0001 (7)	0.0078 (7)	−0.0011 (8)
C5	0.0592 (11)	0.0540 (11)	0.0657 (12)	0.0030 (9)	−0.0018 (9)	0.0046 (9)
C6	0.0740 (14)	0.0486 (12)	0.1004 (17)	0.0041 (10)	0.0046 (13)	0.0025 (11)
C7	0.0807 (15)	0.0570 (13)	0.1052 (19)	−0.0042 (11)	0.0099 (14)	−0.0210 (13)
C8	0.0667 (13)	0.0823 (15)	0.0642 (13)	−0.0117 (11)	0.0007 (10)	−0.0163 (11)
C9	0.0478 (9)	0.0432 (9)	0.0384 (8)	0.0004 (7)	−0.0004 (7)	−0.0031 (7)
C10	0.0557 (11)	0.0626 (12)	0.0470 (10)	0.0063 (9)	0.0004 (8)	0.0076 (8)
C11	0.0692 (13)	0.0724 (14)	0.0463 (10)	−0.0107 (10)	0.0077 (9)	0.0042 (9)
C12	0.0525 (11)	0.0652 (12)	0.0572 (11)	−0.0128 (9)	0.0091 (9)	−0.0235 (9)
C13	0.0495 (11)	0.0650 (12)	0.0705 (13)	0.0103 (9)	−0.0010 (9)	−0.0100 (10)
C14	0.0588 (11)	0.0532 (11)	0.0484 (10)	0.0087 (8)	−0.0013 (8)	0.0033 (8)
C15	0.0654 (14)	0.109 (2)	0.0933 (17)	−0.0258 (13)	0.0296 (12)	−0.0401 (15)

S1—O3	1.4212 (13)	C6—H6	0.9300
S1—O4	1.4262 (14)	C7—C8	1.358 (3)
S1—N1	1.6311 (15)	C7—H7	0.9300
S1—C9	1.7535 (17)	C8—H8	0.9300
O1—C2	1.331 (2)	C9—C10	1.379 (2)
O1—C1	1.440 (3)	C9—C14	1.380 (2)
O2—C2	1.206 (3)	C10—C11	1.367 (3)
N1—C4	1.410 (2)	C10—H10	0.9300
N1—H1	0.8734	C11—C12	1.388 (3)
C1—H1A	0.9600	C11—H11	0.9300
C1—H1B	0.9600	C12—C13	1.374 (3)
C1—H1C	0.9600	C12—C15	1.502 (3)
C2—C3	1.479 (3)	C13—C14	1.379 (3)
C3—C8	1.397 (3)	C13—H13	0.9300
C3—C4	1.407 (2)	C14—H14	0.9300
C4—C5	1.385 (2)	C15—H15A	0.9600
C5—C6	1.373 (3)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—C7	1.372 (3)
O3—S1—O4	119.33 (9)	C8—C7—C6	119.4 (2)
O3—S1—N1	109.45 (8)	C8—C7—H7	120.3
O4—S1—N1	104.03 (8)	C6—C7—H7	120.3
O3—S1—C9	108.24 (8)	C7—C8—C3	122.0 (2)
O4—S1—C9	108.40 (8)	C7—C8—H8	119.0
N1—S1—C9	106.73 (8)	C3—C8—H8	119.0
C2—O1—C1	116.4 (2)	C10—C9—C14	120.39 (17)
C4—N1—S1	126.43 (12)	C10—C9—S1	119.30 (13)
C4—N1—H1	111.6	C14—C9—S1	120.27 (13)
S1—N1—H1	112.8	C11—C10—C9	119.29 (17)
O1—C1—H1A	109.5	C11—C10—H10	120.4
O1—C1—H1B	109.5	C9—C10—H10	120.4
H1A—C1—H1B	109.5	C10—C11—C12	121.63 (18)
O1—C1—H1C	109.5	C10—C11—H11	119.2
H1A—C1—H1C	109.5	C12—C11—H11	119.2
H1B—C1—H1C	109.5	C13—C12—C11	117.99 (17)
O2—C2—O1	122.6 (2)	C13—C12—C15	121.3 (2)
O2—C2—C3	125.93 (19)	C11—C12—C15	120.7 (2)
O1—C2—C3	111.5 (2)	C12—C13—C14	121.46 (18)
C8—C3—C4	118.07 (18)	C12—C13—H13	119.3
C8—C3—C2	121.06 (18)	C14—C13—H13	119.3
C4—C3—C2	120.86 (17)	C13—C14—C9	119.23 (17)
C5—C4—C3	119.06 (17)	C13—C14—H14	120.4
C5—C4—N1	121.75 (16)	C9—C14—H14	120.4
C3—C4—N1	119.14 (16)	C12—C15—H15A	109.5
C6—C5—C4	120.82 (19)	C12—C15—H15B	109.5
C6—C5—H5	119.6	H15A—C15—H15B	109.5
C4—C5—H5	119.6	C12—C15—H15C	109.5
C7—C6—C5	120.6 (2)	H15A—C15—H15C	109.5
C7—C6—H6	119.7	H15B—C15—H15C	109.5
C5—C6—H6	119.7
O3—S1—N1—C4	−53.87 (17)	C6—C7—C8—C3	0.0 (4)
O4—S1—N1—C4	177.55 (15)	C4—C3—C8—C7	−0.1 (3)
C9—S1—N1—C4	63.05 (16)	C2—C3—C8—C7	−178.8 (2)
C1—O1—C2—O2	1.7 (3)	O3—S1—C9—C10	178.84 (13)
C1—O1—C2—C3	−178.72 (17)	O4—S1—C9—C10	−50.38 (16)
O2—C2—C3—C8	178.3 (2)	N1—S1—C9—C10	61.13 (15)
O1—C2—C3—C8	−1.3 (2)	O3—S1—C9—C14	−3.30 (16)
O2—C2—C3—C4	−0.4 (3)	O4—S1—C9—C14	127.47 (15)
O1—C2—C3—C4	−179.97 (15)	N1—S1—C9—C14	−121.02 (14)
C8—C3—C4—C5	0.2 (3)	C14—C9—C10—C11	−0.8 (3)
C2—C3—C4—C5	178.93 (16)	S1—C9—C10—C11	177.06 (14)
C8—C3—C4—N1	−177.13 (16)	C9—C10—C11—C12	0.1 (3)
C2—C3—C4—N1	1.6 (2)	C10—C11—C12—C13	0.3 (3)
S1—N1—C4—C5	34.0 (2)	C10—C11—C12—C15	−179.53 (18)
S1—N1—C4—C3	−148.77 (14)	C11—C12—C13—C14	0.1 (3)
C3—C4—C5—C6	−0.2 (3)	C15—C12—C13—C14	179.90 (18)
N1—C4—C5—C6	177.03 (18)	C12—C13—C14—C9	−0.8 (3)
C4—C5—C6—C7	0.1 (3)	C10—C9—C14—C13	1.2 (3)
C5—C6—C7—C8	0.0 (4)	S1—C9—C14—C13	−176.68 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.87	1.89	2.640 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.87	1.89	2.640 (2)	143