Methyl 2-(N-methoxy-carbonyl-meth-yl-N-methylsulfamo-yl)benzoate.

In the title compound, C(12)H(15)NO(6)S, the aromatic ring is oriented at dihedral angles of 64.76 (11) and 56.42 (13)° with respect to the planar methyl ester unit and the SO(2) group, respectively. The dihedral angle between the SO(2) group and the planar methoxy-carbonyl-methyl group is 50.42 (14)°. Intra-molecular C-H⋯O hydrogen bonding results in the formation of an eight-membered ring. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For general background, see: Hanson et al. (1999 ▶). For related structures, see: Arshad et al. (2008 ▶); Shafiq et al. (2008a ▶,b ▶); Ma et al., 2003 ▶).

Experimental

Crystal data

C12H15NO6S

M = 301.31

Orthorhombic,

a = 8.5830 (3) Å

b = 9.0966 (3) Å

c = 18.3329 (7) Å

V = 1431.36 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 (2) K

0.22 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.942, T max = 0.965

16627 measured reflections

3558 independent reflections

2513 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.098

S = 1.01

3558 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1509 Friedel pairs

Flack parameter: 0.12 (8)

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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003742/hk2618sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003742/hk2618Isup2.hkl

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

C12H15NO6S	F(000) = 632
Mr = 301.31	Dx = 1.398 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3558 reflections
a = 8.5830 (3) Å	θ = 2.2–28.3°
b = 9.0966 (3) Å	µ = 0.25 mm−1
c = 18.3329 (7) Å	T = 296 K
V = 1431.36 (9) Å3	Prism, colorless
Z = 4	0.22 × 0.18 × 0.15 mm

Bruker Kappa APEXII CCD diffractometer	3558 independent reflections
Radiation source: fine-focus sealed tube	2513 reflections with I > 2σ(I)
graphite	Rint = 0.039
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 2.2°
ω scans	h = −11→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→10
Tmin = 0.942, Tmax = 0.965	l = −24→24
16627 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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.0688P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3558 reflections	Δρmax = 0.16 e Å−3
184 parameters	Δρmin = −0.24 e Å−3
0 restraints	Absolute structure: Flack (1983), 1509 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.12 (8)

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	0.48790 (6)	0.03278 (6)	0.16077 (3)	0.0454 (2)
O1	0.78607 (18)	0.0316 (2)	0.03285 (9)	0.0594 (6)
O2	0.8987 (2)	−0.15351 (18)	0.09228 (8)	0.0578 (6)
O3	0.5106 (2)	−0.09093 (17)	0.11432 (8)	0.0528 (5)
O4	0.3864 (2)	0.0227 (2)	0.22151 (9)	0.0730 (7)
O5	0.1989 (2)	0.0586 (2)	0.01831 (11)	0.0744 (8)
O6	0.3568 (3)	0.0937 (2)	−0.07700 (10)	0.0802 (8)
N1	0.4279 (2)	0.1681 (2)	0.11144 (10)	0.0534 (7)
C1	0.6735 (3)	0.0822 (2)	0.19630 (11)	0.0437 (7)
C2	0.6751 (3)	0.1563 (3)	0.26251 (12)	0.0581 (8)
C3	0.8149 (4)	0.1958 (3)	0.29366 (16)	0.0783 (11)
C4	0.9518 (4)	0.1598 (3)	0.26066 (17)	0.0883 (12)
C5	0.9524 (3)	0.0831 (3)	0.19607 (15)	0.0705 (10)
C6	0.8129 (3)	0.0454 (2)	0.16210 (12)	0.0453 (7)
C7	0.8263 (2)	−0.0253 (3)	0.08873 (12)	0.0451 (7)
C8	0.9334 (3)	−0.2224 (3)	0.02298 (14)	0.0691 (10)
C9	0.4512 (3)	0.1665 (3)	0.03348 (12)	0.0551 (8)
C10	0.3184 (3)	0.0993 (3)	−0.00666 (13)	0.0524 (8)
C11	0.3366 (4)	0.2883 (3)	0.14377 (16)	0.0815 (11)
C12	0.2408 (5)	0.0357 (5)	−0.12639 (17)	0.1163 (16)
H2	0.58187	0.17913	0.28577	0.0698*
H3	0.81583	0.24736	0.33747	0.0940*
H4	1.04565	0.18742	0.28200	0.1058*
H5	1.04666	0.05609	0.17491	0.0846*
H8A	0.83789	−0.24343	−0.00223	0.1037*
H8B	0.98933	−0.31225	0.03123	0.1037*
H8C	0.99584	−0.15722	−0.00600	0.1037*
H9A	0.54547	0.11201	0.02250	0.0661*
H9B	0.46577	0.26658	0.01653	0.0661*
H11A	0.37475	0.38079	0.12602	0.1224*
H11B	0.34631	0.28520	0.19591	0.1224*
H11C	0.22901	0.27731	0.13049	0.1224*
H12A	0.21196	−0.06164	−0.11128	0.1744*
H12B	0.28284	0.03215	−0.17488	0.1744*
H12C	0.15056	0.09800	−0.12580	0.1744*

	U11	U22	U33	U12	U13	U23
S1	0.0541 (3)	0.0436 (3)	0.0386 (3)	−0.0130 (3)	0.0029 (3)	−0.0013 (3)
O1	0.0599 (9)	0.0687 (12)	0.0497 (9)	0.0096 (9)	0.0026 (8)	0.0119 (9)
O2	0.0758 (11)	0.0440 (10)	0.0535 (10)	0.0095 (9)	−0.0038 (8)	−0.0040 (8)
O3	0.0687 (10)	0.0402 (8)	0.0495 (8)	−0.0140 (8)	−0.0024 (9)	−0.0063 (7)
O4	0.0796 (11)	0.0836 (13)	0.0558 (10)	−0.0252 (11)	0.0226 (9)	−0.0036 (10)
O5	0.0505 (10)	0.0879 (16)	0.0849 (13)	−0.0031 (10)	−0.0139 (10)	−0.0223 (12)
O6	0.1054 (14)	0.0852 (14)	0.0501 (11)	0.0268 (12)	−0.0149 (10)	−0.0049 (10)
N1	0.0599 (11)	0.0491 (12)	0.0511 (11)	0.0039 (9)	−0.0131 (9)	−0.0068 (10)
C1	0.0611 (13)	0.0340 (12)	0.0360 (11)	−0.0023 (10)	−0.0100 (10)	0.0024 (9)
C2	0.0782 (16)	0.0507 (15)	0.0455 (13)	0.0060 (14)	−0.0108 (12)	−0.0074 (12)
C3	0.100 (2)	0.069 (2)	0.0658 (18)	0.0140 (18)	−0.0382 (17)	−0.0274 (15)
C4	0.084 (2)	0.077 (2)	0.104 (2)	0.0090 (17)	−0.0509 (18)	−0.0333 (19)
C5	0.0603 (15)	0.0640 (18)	0.0873 (19)	0.0066 (13)	−0.0235 (14)	−0.0177 (15)
C6	0.0534 (11)	0.0350 (13)	0.0476 (12)	0.0020 (10)	−0.0107 (11)	−0.0001 (11)
C7	0.0418 (11)	0.0428 (13)	0.0506 (13)	−0.0012 (10)	−0.0020 (10)	0.0018 (11)
C8	0.0825 (18)	0.0591 (18)	0.0657 (16)	0.0050 (14)	0.0069 (14)	−0.0177 (14)
C9	0.0541 (13)	0.0553 (16)	0.0559 (14)	−0.0002 (11)	−0.0089 (11)	0.0131 (12)
C10	0.0553 (14)	0.0493 (14)	0.0526 (15)	0.0177 (12)	−0.0147 (12)	−0.0042 (12)
C11	0.0798 (19)	0.0618 (19)	0.103 (2)	0.0132 (16)	−0.0086 (17)	−0.0203 (17)
C12	0.148 (3)	0.124 (3)	0.077 (2)	0.057 (3)	−0.064 (2)	−0.044 (2)

S1—O3	1.4246 (16)	C6—C7	1.495 (3)
S1—O4	1.4168 (18)	C9—C10	1.488 (4)
S1—N1	1.6119 (19)	C2—H2	0.9300
S1—C1	1.779 (3)	C3—H3	0.9300
O1—C7	1.199 (3)	C4—H4	0.9300
O2—C7	1.323 (3)	C5—H5	0.9300
O2—C8	1.448 (3)	C8—H8A	0.9600
O5—C10	1.183 (3)	C8—H8B	0.9600
O6—C10	1.332 (3)	C8—H8C	0.9600
O6—C12	1.446 (4)	C9—H9A	0.9700
N1—C9	1.443 (3)	C9—H9B	0.9700
N1—C11	1.470 (3)	C11—H11A	0.9600
C1—C2	1.389 (3)	C11—H11B	0.9600
C1—C6	1.392 (3)	C11—H11C	0.9600
C2—C3	1.377 (4)	C12—H12A	0.9600
C3—C4	1.362 (5)	C12—H12B	0.9600
C4—C5	1.374 (4)	C12—H12C	0.9600
C5—C6	1.393 (4)
S1···O1	3.4712 (17)	C9···O1	3.125 (3)
O1···S1	3.4712 (17)	C9···O1v	3.321 (3)
O1···O3	3.011 (2)	C9···O5i	3.417 (3)
O1···C9	3.125 (3)	C10···O3	3.261 (3)
O1···C9i	3.321 (3)	C10···C8ii	3.580 (4)
O1···C10i	3.403 (3)	C10···O1v	3.403 (3)
O3···O1	3.011 (2)	C11···O5	3.325 (3)
O3···C8ii	3.108 (3)	C12···O4x	3.041 (4)
O3···C7	2.814 (2)	C7···H9A	2.9700
O3···C10	3.261 (3)	C10···H11C	3.0900
O4···C12iii	3.041 (4)	C10···H8Bii	3.0300
O4···C2iv	3.387 (3)	C11···H12Ci	2.9100
O5···N1	2.788 (3)	H2···O4	2.5000
O5···C11	3.325 (3)	H2···O3viii	2.8900
O5···C9v	3.417 (3)	H3···O2xi	2.9100
O1···H8C	2.5900	H4···O2xi	2.7600
O1···H9Bi	2.5600	H5···O2	2.7500
O1···H8A	2.6200	H8A···O1	2.6200
O1···H9A	2.2000	H8B···O3ix	2.8200
O2···H4vi	2.7600	H8B···C10ix	3.0300
O2···H5	2.7500	H8C···O1	2.5900
O2···H3vi	2.9100	H8C···O5xii	2.6600
O3···H2iv	2.8900	H9A···O1	2.2000
O3···H8Bii	2.8200	H9A···O3	2.5200
O3···H9A	2.5200	H9A···C7	2.9700
O4···H2	2.5000	H9B···H11A	2.3900
O4···H11B	2.4600	H9B···O1v	2.5600
O4···H12Biii	2.4400	H9B···O5i	2.6300
O5···H8Cvii	2.6600	H11A···H9B	2.3900
O5···H12A	2.6200	H11A···H12Ci	2.3800
O5···H12C	2.7000	H11B···O4	2.4600
O5···H11C	2.8700	H11C···O5	2.8700
O5···H9Bv	2.6300	H11C···C10	3.0900
N1···O5	2.788 (3)	H12A···O5	2.6200
N1···H12Ci	2.8700	H12B···O4x	2.4400
C2···O4viii	3.387 (3)	H12C···O5	2.7000
C7···O3	2.814 (2)	H12C···N1v	2.8700
C8···O3ix	3.108 (3)	H12C···C11v	2.9100
C8···C10ix	3.580 (4)	H12C···H11Av	2.3800
O3—S1—O4	120.18 (10)	C2—C3—H3	120.00
O3—S1—N1	108.15 (10)	C4—C3—H3	120.00
O3—S1—C1	107.22 (10)	C3—C4—H4	120.00
O4—S1—N1	107.09 (10)	C5—C4—H4	120.00
O4—S1—C1	106.21 (10)	C4—C5—H5	120.00
N1—S1—C1	107.37 (9)	C6—C5—H5	120.00
C7—O2—C8	115.79 (18)	O2—C8—H8A	109.00
C10—O6—C12	116.7 (3)	O2—C8—H8B	109.00
S1—N1—C9	120.24 (16)	O2—C8—H8C	109.00
S1—N1—C11	120.81 (16)	H8A—C8—H8B	109.00
C9—N1—C11	118.7 (2)	H8A—C8—H8C	109.00
S1—C1—C2	116.85 (19)	H8B—C8—H8C	110.00
S1—C1—C6	122.97 (16)	N1—C9—H9A	109.00
C2—C1—C6	120.1 (2)	N1—C9—H9B	109.00
C1—C2—C3	119.9 (2)	C10—C9—H9A	109.00
C2—C3—C4	120.3 (3)	C10—C9—H9B	109.00
C3—C4—C5	120.5 (3)	H9A—C9—H9B	108.00
C4—C5—C6	120.5 (3)	N1—C11—H11A	109.00
C1—C6—C5	118.6 (2)	N1—C11—H11B	109.00
C1—C6—C7	125.1 (2)	N1—C11—H11C	109.00
C5—C6—C7	116.2 (2)	H11A—C11—H11B	109.00
O1—C7—O2	123.9 (2)	H11A—C11—H11C	109.00
O1—C7—C6	124.1 (2)	H11B—C11—H11C	109.00
O2—C7—C6	111.78 (18)	O6—C12—H12A	109.00
N1—C9—C10	112.8 (2)	O6—C12—H12B	109.00
O5—C10—O6	125.3 (2)	O6—C12—H12C	109.00
O5—C10—C9	127.0 (2)	H12A—C12—H12B	109.00
O6—C10—C9	107.8 (2)	H12A—C12—H12C	109.00
C1—C2—H2	120.00	H12B—C12—H12C	109.00
C3—C2—H2	120.00
O3—S1—N1—C9	−19.1 (2)	S1—C1—C2—C3	179.0 (2)
O3—S1—N1—C11	155.37 (19)	C6—C1—C2—C3	1.2 (3)
O4—S1—N1—C9	−149.96 (17)	S1—C1—C6—C5	−176.98 (17)
O4—S1—N1—C11	24.5 (2)	S1—C1—C6—C7	6.6 (3)
C1—S1—N1—C9	96.32 (18)	C2—C1—C6—C5	0.7 (3)
C1—S1—N1—C11	−89.2 (2)	C2—C1—C6—C7	−175.8 (2)
O3—S1—C1—C2	−154.78 (17)	C1—C2—C3—C4	−1.4 (4)
O3—S1—C1—C6	22.94 (19)	C2—C3—C4—C5	−0.3 (4)
O4—S1—C1—C2	−25.1 (2)	C3—C4—C5—C6	2.2 (4)
O4—S1—C1—C6	152.60 (17)	C4—C5—C6—C1	−2.4 (4)
N1—S1—C1—C2	89.20 (19)	C4—C5—C6—C7	174.4 (2)
N1—S1—C1—C6	−93.09 (18)	C1—C6—C7—O1	64.8 (3)
C8—O2—C7—O1	2.1 (3)	C1—C6—C7—O2	−120.0 (2)
C8—O2—C7—C6	−173.08 (19)	C5—C6—C7—O1	−111.8 (2)
C12—O6—C10—O5	1.3 (4)	C5—C6—C7—O2	63.4 (3)
C12—O6—C10—C9	−178.1 (3)	N1—C9—C10—O5	5.0 (4)
S1—N1—C9—C10	91.0 (2)	N1—C9—C10—O6	−175.5 (2)
C11—N1—C9—C10	−83.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.97	2.20	3.125 (3)	159
C9—H9B···O1v	0.97	2.56	3.321 (3)	135
C12—H12B···O4x	0.96	2.44	3.041 (4)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1	0.97	2.20	3.125 (3)	159
C9—H9B⋯O1i	0.97	2.56	3.321 (3)	135
C12—H12B⋯O4ii	0.96	2.44	3.041 (4)	120

Symmetry codes: (i) ; (ii) .