Methyl 2-(N-ethyl-methane-sulfonamido)benzoate.

In the mol-ecule of the title compound, C(11)H(15)NO(4)S, the S atom environment is distorted tetrahedral. The methoxy-carbonyl group is oriented at a dihedral angle of 11.8 (2)° with respect to the benzene ring. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For general background, see: Reissenweber & Mangold (1982 ▶); Mookherjee et al. (1989 ▶); Tadashi et al. (1982 ▶). For related literature, see: Siddiqui et al. (2006 ▶,2007a ▶,b ▶); Lombardino (1972 ▶); Hanson & Hitchcook (2004 ▶).

Experimental

Crystal data

C11H15NO4S

M = 257.30

Triclinic,

a = 8.0161 (4) Å

b = 8.4386 (4) Å

c = 10.5329 (5) Å

α = 85.244 (3)°

β = 78.721 (3)°

γ = 62.650 (3)°

V = 620.61 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 296 (2) K

0.25 × 0.18 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005) T min = 0.935, T max = 0.958

11895 measured reflections

3012 independent reflections

1817 reflections with I > 3σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.00

3012 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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, 2003 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800007X/hk2412sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800007X/hk2412Isup2.hkl

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

C11H15NO4S	Z = 2
Mr = 257.30	F000 = 272
Triclinic, P1	Dx = 1.377 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.0161 (4) Å	Cell parameters from 3596 reflections
b = 8.4386 (4) Å	θ = 2.7–24.8º
c = 10.5329 (5) Å	µ = 0.26 mm−1
α = 85.244 (3)º	T = 296 (2) K
β = 78.721 (3)º	Prismatic, colourless
γ = 62.650 (3)º	0.25 × 0.18 × 0.12 mm
V = 620.61 (5) Å3

Bruker KAPPA APEXII CCD diffractometer	3012 independent reflections
Radiation source: fine-focus sealed tube	1817 reflections with I > 3σ(I)
Monochromator: graphite	Rint = 0.032
Detector resolution: 8.33 pixels mm-1	θmax = 28.3º
T = 296(2) K	θmin = 2.0º
ω scans	h = −10→10
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.935, Tmax = 0.958	l = −14→14
11895 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0727P)2 + 0.1532P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3012 reflections	Δρmax = 0.37 e Å−3
154 parameters	Δρmin = −0.36 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
S1	0.14595 (10)	0.13878 (8)	0.07989 (5)	0.0507 (2)
O1	−0.0510 (3)	0.1954 (3)	0.08167 (19)	0.0688 (6)
O2	0.2655 (3)	0.1495 (3)	−0.03718 (16)	0.0707 (6)
O3	0.2630 (3)	0.0251 (3)	0.40332 (17)	0.0811 (7)
O4	0.0983 (3)	0.1413 (3)	0.59441 (16)	0.0700 (6)
N1	0.1604 (3)	0.2545 (3)	0.18962 (17)	0.0457 (5)
C1	−0.0041 (3)	0.3538 (3)	0.2846 (2)	0.0443 (6)
C2	−0.0200 (3)	0.3048 (3)	0.4158 (2)	0.0436 (6)
C3	−0.1825 (4)	0.4142 (4)	0.5006 (3)	0.0605 (7)
H3	−0.195	0.3845	0.5878	0.073*
C4	−0.3251 (4)	0.5646 (4)	0.4595 (4)	0.0758 (9)
H4	−0.4337	0.6344	0.5181	0.091*
C5	−0.3076 (5)	0.6121 (4)	0.3320 (4)	0.0801 (10)
H5	−0.4039	0.7146	0.3039	0.096*
C6	−0.1476 (4)	0.5080 (4)	0.2458 (3)	0.0654 (8)
H6	−0.1356	0.542	0.1596	0.078*
C7	0.3401 (4)	0.2613 (4)	0.1897 (2)	0.0565 (7)
H7A	0.4445	0.1594	0.1417	0.068*
H7B	0.3614	0.2524	0.2781	0.068*
C8	0.3412 (5)	0.4294 (5)	0.1310 (3)	0.0872 (11)
H8A	0.4615	0.427	0.1332	0.131*
H8B	0.2402	0.5307	0.1794	0.131*
H8C	0.3228	0.4378	0.0429	0.131*
C9	0.2485 (4)	−0.0838 (3)	0.1283 (2)	0.0573 (7)
H9A	0.3819	−0.1245	0.1276	0.086*
H9B	0.2333	−0.1556	0.0697	0.086*
H9C	0.1866	−0.0938	0.2141	0.086*
C10	0.1286 (4)	0.1421 (3)	0.4659 (2)	0.0457 (6)
C11	0.2403 (5)	−0.0050 (4)	0.6546 (3)	0.0754 (9)
H11A	0.204	0.0075	0.747	0.113*
H11B	0.3615	−0.0042	0.6282	0.113*
H11C	0.2499	−0.1157	0.6285	0.113*

	U11	U22	U33	U12	U13	U23
S1	0.0718 (5)	0.0469 (4)	0.0342 (3)	−0.0235 (3)	−0.0201 (3)	0.0011 (2)
O1	0.0720 (13)	0.0634 (12)	0.0718 (12)	−0.0208 (10)	−0.0347 (10)	−0.0126 (9)
O2	0.1094 (17)	0.0694 (13)	0.0324 (9)	−0.0411 (12)	−0.0106 (9)	0.0037 (8)
O3	0.0977 (16)	0.0587 (12)	0.0408 (10)	0.0047 (11)	−0.0141 (10)	−0.0030 (9)
O4	0.0661 (13)	0.0920 (15)	0.0355 (9)	−0.0220 (11)	−0.0101 (9)	0.0021 (9)
N1	0.0579 (13)	0.0471 (11)	0.0337 (9)	−0.0239 (10)	−0.0109 (9)	−0.0018 (8)
C1	0.0527 (15)	0.0365 (12)	0.0475 (12)	−0.0200 (11)	−0.0169 (11)	−0.0023 (9)
C2	0.0484 (14)	0.0446 (13)	0.0417 (12)	−0.0224 (12)	−0.0104 (11)	−0.0062 (10)
C3	0.0547 (17)	0.0681 (18)	0.0569 (15)	−0.0256 (15)	−0.0035 (13)	−0.0186 (13)
C4	0.0540 (19)	0.065 (2)	0.095 (2)	−0.0127 (16)	−0.0083 (17)	−0.0345 (17)
C5	0.067 (2)	0.0508 (17)	0.106 (3)	−0.0015 (15)	−0.038 (2)	−0.0169 (17)
C6	0.079 (2)	0.0450 (15)	0.0677 (17)	−0.0174 (15)	−0.0307 (16)	0.0023 (12)
C7	0.0632 (17)	0.0686 (17)	0.0439 (13)	−0.0347 (15)	−0.0087 (12)	−0.0046 (12)
C8	0.122 (3)	0.094 (3)	0.075 (2)	−0.077 (2)	−0.013 (2)	0.0089 (18)
C9	0.0779 (19)	0.0455 (14)	0.0483 (14)	−0.0252 (14)	−0.0173 (13)	−0.0010 (11)
C10	0.0556 (16)	0.0491 (14)	0.0348 (11)	−0.0255 (13)	−0.0077 (11)	−0.0016 (10)
C11	0.082 (2)	0.095 (2)	0.0440 (14)	−0.0339 (18)	−0.0227 (15)	0.0166 (14)

S1—O1	1.421 (2)	C4—H4	0.93
S1—O2	1.4303 (19)	C5—C6	1.372 (4)
S1—N1	1.6269 (18)	C5—H5	0.93
S1—C9	1.747 (2)	C6—H6	0.93
O3—C10	1.193 (3)	C7—C8	1.503 (4)
O4—C10	1.328 (3)	C7—H7A	0.97
O4—C11	1.443 (3)	C7—H7B	0.97
N1—C1	1.431 (3)	C8—H8A	0.96
N1—C7	1.468 (3)	C8—H8B	0.96
C1—C6	1.380 (3)	C8—H8C	0.96
C1—C2	1.408 (3)	C9—H9A	0.96
C2—C3	1.387 (3)	C9—H9B	0.96
C2—C10	1.485 (3)	C9—H9C	0.96
C3—C4	1.369 (4)	C11—H11A	0.96
C3—H3	0.93	C11—H11B	0.96
C4—C5	1.368 (5)	C11—H11C	0.96
O1—S1—O2	119.88 (12)	N1—C7—C8	112.8 (2)
O1—S1—N1	107.29 (11)	N1—C7—H7A	109
O2—S1—N1	107.34 (11)	C8—C7—H7A	109
O1—S1—C9	108.32 (13)	N1—C7—H7B	109
O2—S1—C9	106.53 (13)	C8—C7—H7B	109
N1—S1—C9	106.83 (11)	H7A—C7—H7B	107.8
C10—O4—C11	116.5 (2)	C7—C8—H8A	109.5
C1—N1—C7	119.82 (18)	C7—C8—H8B	109.5
C1—N1—S1	119.87 (16)	H8A—C8—H8B	109.5
C7—N1—S1	120.29 (16)	C7—C8—H8C	109.5
C6—C1—C2	119.3 (2)	H8A—C8—H8C	109.5
C6—C1—N1	118.0 (2)	H8B—C8—H8C	109.5
C2—C1—N1	122.6 (2)	S1—C9—H9A	109.5
C3—C2—C1	117.9 (2)	S1—C9—H9B	109.5
C3—C2—C10	119.3 (2)	H9A—C9—H9B	109.5
C1—C2—C10	122.8 (2)	S1—C9—H9C	109.5
C4—C3—C2	121.8 (3)	H9A—C9—H9C	109.5
C4—C3—H3	119.1	H9B—C9—H9C	109.5
C2—C3—H3	119.1	O3—C10—O4	121.8 (2)
C5—C4—C3	119.9 (3)	O3—C10—C2	126.8 (2)
C5—C4—H4	120	O4—C10—C2	111.4 (2)
C3—C4—H4	120	O4—C11—H11A	109.5
C4—C5—C6	119.7 (3)	O4—C11—H11B	109.5
C4—C5—H5	120.1	H11A—C11—H11B	109.5
C6—C5—H5	120.1	O4—C11—H11C	109.5
C5—C6—C1	121.3 (3)	H11A—C11—H11C	109.5
C5—C6—H6	119.3	H11B—C11—H11C	109.5
C1—C6—H6	119.3
O1—S1—N1—C1	14.2 (2)	C10—C2—C3—C4	−179.2 (2)
O2—S1—N1—C1	144.26 (18)	C2—C3—C4—C5	−1.2 (4)
C9—S1—N1—C1	−101.8 (2)	C3—C4—C5—C6	0.4 (5)
O1—S1—N1—C7	−164.23 (18)	C4—C5—C6—C1	1.0 (5)
O2—S1—N1—C7	−34.2 (2)	C2—C1—C6—C5	−1.7 (4)
C9—S1—N1—C7	79.8 (2)	N1—C1—C6—C5	−178.6 (3)
C7—N1—C1—C6	104.8 (3)	C1—N1—C7—C8	−78.2 (3)
S1—N1—C1—C6	−73.6 (3)	S1—N1—C7—C8	100.3 (2)
C7—N1—C1—C2	−72.0 (3)	C11—O4—C10—O3	2.3 (4)
S1—N1—C1—C2	109.6 (2)	C11—O4—C10—C2	−176.2 (2)
C6—C1—C2—C3	0.9 (3)	C3—C2—C10—O3	170.1 (3)
N1—C1—C2—C3	177.6 (2)	C1—C2—C10—O3	−9.6 (4)
C6—C1—C2—C10	−179.4 (2)	C3—C2—C10—O4	−11.5 (3)
N1—C1—C2—C10	−2.7 (3)	C1—C2—C10—O4	168.9 (2)
C1—C2—C3—C4	0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O1i	0.96	2.50	3.372 (5)	151
C7—H7B···O3	0.97	2.57	3.044 (4)	110
C9—H9C···O3	0.96	2.59	3.152 (4)	117

S1—O1	1.421 (2)
S1—O2	1.4303 (19)
S1—N1	1.6269 (18)
S1—C9	1.747 (2)

O1—S1—O2	119.88 (12)
O1—S1—N1	107.29 (11)
O2—S1—N1	107.34 (11)
O1—S1—C9	108.32 (13)
O2—S1—C9	106.53 (13)
N1—S1—C9	106.83 (11)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O1i	0.96	2.50	3.372 (5)	151
C7—H7B⋯O3	0.97	2.57	3.044 (4)	110
C9—H9C⋯O3	0.96	2.59	3.152 (4)	117

Symmetry code: (i) .