N-(4-Methyl-phenyl-sulfon-yl)succinamic acid.

In the crystal structure of the title compound, C(11)H(13)NO(5)S, the amide C=O and the carboxyl C=O groups of the acid segment orient themselves away from each other. The dihedral angle between the benzene ring and the amide group is 69.0 (2)°. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the bc plane.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶); Saraswathi et al. (2011 ▶), of N-chloro­aryl­amides, see: Gowda & Rao (1989 ▶); Jyothi & Gowda (2004 ▶) and of N-bromo­aryl­sulfonamides, see: Gowda & Mahadevappa (1983 ▶); Usha & Gowda (2006 ▶).

Experimental

Crystal data

C11H13NO5S

M = 271.28

Monoclinic,

a = 10.2496 (9) Å

b = 17.041 (2) Å

c = 7.4721 (6) Å

β = 101.909 (9)°

V = 1277.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.48 × 0.32 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.883, T max = 0.959

4739 measured reflections

2597 independent reflections

2107 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.110

S = 1.12

2597 reflections

170 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023276/rz2761sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023276/rz2761Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023276/rz2761Isup3.cml

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

C11H13NO5S	F(000) = 568
Mr = 271.28	Dx = 1.411 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2495 reflections
a = 10.2496 (9) Å	θ = 3.0–27.6°
b = 17.041 (2) Å	µ = 0.27 mm−1
c = 7.4721 (6) Å	T = 293 K
β = 101.909 (9)°	Prism, colourless
V = 1277.0 (2) Å3	0.48 × 0.32 × 0.16 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2597 independent reflections
Radiation source: fine-focus sealed tube	2107 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −12→11
Tmin = 0.883, Tmax = 0.959	k = −21→8
4739 measured reflections	l = −9→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.034P)2 + 0.9166P] where P = (Fo2 + 2Fc2)/3
2597 reflections	(Δ/σ)max = 0.001
170 parameters	Δρmax = 0.23 e Å−3
2 restraints	Δρmin = −0.32 e Å−3

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.1649 (2)	0.82620 (14)	0.0924 (3)	0.0398 (5)
C2	0.1077 (3)	0.75638 (15)	0.0207 (4)	0.0507 (6)
H2	0.1604	0.7126	0.0132	0.061*
C3	−0.0291 (3)	0.75296 (17)	−0.0394 (4)	0.0625 (7)
H3	−0.0682	0.7063	−0.0881	0.075*
C4	−0.1092 (3)	0.81770 (18)	−0.0286 (4)	0.0607 (7)
C5	−0.0496 (3)	0.88660 (16)	0.0469 (4)	0.0582 (7)
H5	−0.1025	0.9301	0.0572	0.070*
C6	0.0864 (3)	0.89152 (14)	0.1068 (4)	0.0482 (6)
H6	0.1255	0.9381	0.1563	0.058*
C7	0.3668 (2)	0.93791 (13)	−0.0993 (3)	0.0349 (5)
C8	0.4086 (2)	0.94773 (14)	−0.2799 (3)	0.0394 (5)
H8A	0.3879	0.9001	−0.3514	0.047*
H8B	0.5042	0.9557	−0.2582	0.047*
C9	0.3388 (2)	1.01660 (14)	−0.3874 (3)	0.0439 (6)
H9A	0.3582	1.0638	−0.3143	0.053*
H9B	0.3743	1.0236	−0.4971	0.053*
C10	0.1912 (2)	1.00645 (14)	−0.4408 (3)	0.0419 (5)
C11	−0.2586 (3)	0.8130 (2)	−0.0975 (6)	0.0995 (13)
H11A	−0.2856	0.7590	−0.1091	0.119*
H11B	−0.2822	0.8382	−0.2147	0.119*
H11C	−0.3029	0.8389	−0.0126	0.119*
N1	0.3902 (2)	0.86326 (11)	−0.0248 (2)	0.0387 (4)
H1N	0.404 (3)	0.8261 (12)	−0.090 (3)	0.046*
O1	0.39301 (18)	0.75502 (11)	0.1880 (2)	0.0565 (5)
O2	0.37311 (18)	0.89014 (11)	0.2992 (2)	0.0558 (5)
O3	0.32175 (17)	0.99012 (10)	−0.0214 (2)	0.0479 (4)
O4	0.13237 (16)	0.94917 (10)	−0.4003 (3)	0.0552 (5)
O5	0.13192 (19)	1.06525 (12)	−0.5367 (3)	0.0672 (6)
H5O	0.0496 (18)	1.0596 (19)	−0.557 (4)	0.081*
S1	0.33860 (6)	0.83267 (4)	0.15920 (7)	0.04120 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0465 (13)	0.0405 (13)	0.0342 (11)	−0.0018 (10)	0.0130 (9)	0.0004 (10)
C2	0.0567 (15)	0.0388 (13)	0.0565 (15)	0.0028 (12)	0.0116 (12)	−0.0042 (12)
C3	0.0639 (18)	0.0487 (16)	0.0723 (19)	−0.0113 (14)	0.0080 (14)	−0.0089 (14)
C4	0.0482 (15)	0.0634 (18)	0.0701 (18)	−0.0024 (13)	0.0112 (13)	0.0047 (15)
C5	0.0537 (16)	0.0479 (15)	0.0771 (19)	0.0076 (13)	0.0230 (14)	0.0025 (14)
C6	0.0562 (15)	0.0359 (13)	0.0564 (15)	−0.0021 (11)	0.0209 (12)	−0.0030 (11)
C7	0.0315 (11)	0.0392 (12)	0.0328 (11)	−0.0044 (9)	0.0038 (9)	−0.0022 (9)
C8	0.0365 (12)	0.0479 (13)	0.0336 (11)	−0.0005 (10)	0.0072 (9)	0.0029 (10)
C9	0.0405 (12)	0.0479 (14)	0.0430 (12)	−0.0051 (11)	0.0082 (10)	0.0080 (11)
C10	0.0464 (13)	0.0400 (13)	0.0376 (12)	0.0007 (11)	0.0047 (10)	0.0042 (10)
C11	0.054 (2)	0.098 (3)	0.140 (4)	−0.0050 (19)	0.003 (2)	−0.001 (3)
N1	0.0485 (11)	0.0360 (10)	0.0341 (10)	0.0027 (9)	0.0142 (8)	−0.0011 (8)
O1	0.0609 (11)	0.0531 (11)	0.0559 (11)	0.0110 (9)	0.0129 (9)	0.0202 (9)
O2	0.0649 (11)	0.0689 (12)	0.0326 (8)	−0.0113 (10)	0.0075 (8)	−0.0062 (8)
O3	0.0580 (10)	0.0423 (10)	0.0467 (9)	0.0046 (8)	0.0181 (8)	−0.0041 (8)
O4	0.0420 (9)	0.0466 (10)	0.0718 (12)	−0.0054 (8)	−0.0001 (8)	0.0162 (9)
O5	0.0451 (10)	0.0579 (12)	0.0924 (15)	0.0011 (9)	0.0001 (10)	0.0301 (11)
S1	0.0478 (3)	0.0445 (3)	0.0315 (3)	−0.0001 (3)	0.0087 (2)	0.0046 (2)

C1—C2	1.385 (3)	C8—H8A	0.9700
C1—C6	1.390 (3)	C8—H8B	0.9700
C1—S1	1.750 (2)	C9—C10	1.493 (3)
C2—C3	1.382 (4)	C9—H9A	0.9700
C2—H2	0.9300	C9—H9B	0.9700
C3—C4	1.387 (4)	C10—O4	1.218 (3)
C3—H3	0.9300	C10—O5	1.307 (3)
C4—C5	1.388 (4)	C11—H11A	0.9600
C4—C11	1.514 (4)	C11—H11B	0.9600
C5—C6	1.377 (4)	C11—H11C	0.9600
C5—H5	0.9300	N1—S1	1.6559 (19)
C6—H6	0.9300	N1—H1N	0.828 (16)
C7—O3	1.206 (3)	O1—S1	1.4349 (19)
C7—N1	1.390 (3)	O2—S1	1.4234 (18)
C7—C8	1.507 (3)	O5—H5O	0.832 (18)
C8—C9	1.516 (3)
C2—C1—C6	120.8 (2)	H8A—C8—H8B	107.9
C2—C1—S1	119.28 (19)	C10—C9—C8	113.14 (19)
C6—C1—S1	119.88 (19)	C10—C9—H9A	109.0
C3—C2—C1	118.8 (2)	C8—C9—H9A	109.0
C3—C2—H2	120.6	C10—C9—H9B	109.0
C1—C2—H2	120.6	C8—C9—H9B	109.0
C2—C3—C4	121.3 (3)	H9A—C9—H9B	107.8
C2—C3—H3	119.3	O4—C10—O5	123.6 (2)
C4—C3—H3	119.3	O4—C10—C9	123.6 (2)
C3—C4—C5	118.7 (3)	O5—C10—C9	112.9 (2)
C3—C4—C11	120.5 (3)	C4—C11—H11A	109.5
C5—C4—C11	120.8 (3)	C4—C11—H11B	109.5
C6—C5—C4	121.0 (2)	H11A—C11—H11B	109.5
C6—C5—H5	119.5	C4—C11—H11C	109.5
C4—C5—H5	119.5	H11A—C11—H11C	109.5
C5—C6—C1	119.3 (2)	H11B—C11—H11C	109.5
C5—C6—H6	120.3	C7—N1—S1	124.26 (16)
C1—C6—H6	120.3	C7—N1—H1N	120.1 (18)
O3—C7—N1	122.2 (2)	S1—N1—H1N	111.6 (18)
O3—C7—C8	123.9 (2)	C10—O5—H5O	111 (2)
N1—C7—C8	113.78 (19)	O2—S1—O1	119.62 (11)
C7—C8—C9	111.76 (19)	O2—S1—N1	108.68 (10)
C7—C8—H8A	109.3	O1—S1—N1	103.54 (10)
C9—C8—H8A	109.3	O2—S1—C1	109.68 (11)
C7—C8—H8B	109.3	O1—S1—C1	109.01 (11)
C9—C8—H8B	109.3	N1—S1—C1	105.27 (10)
C6—C1—C2—C3	1.0 (4)	C8—C9—C10—O4	0.8 (3)
S1—C1—C2—C3	−177.0 (2)	C8—C9—C10—O5	−178.6 (2)
C1—C2—C3—C4	−0.2 (4)	O3—C7—N1—S1	10.0 (3)
C2—C3—C4—C5	−0.9 (5)	C8—C7—N1—S1	−172.55 (15)
C2—C3—C4—C11	179.2 (3)	C7—N1—S1—O2	−48.4 (2)
C3—C4—C5—C6	1.3 (4)	C7—N1—S1—O1	−176.60 (18)
C11—C4—C5—C6	−178.8 (3)	C7—N1—S1—C1	69.0 (2)
C4—C5—C6—C1	−0.5 (4)	C2—C1—S1—O2	−153.06 (19)
C2—C1—C6—C5	−0.7 (4)	C6—C1—S1—O2	28.8 (2)
S1—C1—C6—C5	177.4 (2)	C2—C1—S1—O1	−20.3 (2)
O3—C7—C8—C9	−23.2 (3)	C6—C1—S1—O1	161.55 (18)
N1—C7—C8—C9	159.36 (19)	C2—C1—S1—N1	90.2 (2)
C7—C8—C9—C10	−63.7 (3)	C6—C1—S1—N1	−87.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (2)	2.14 (2)	2.948 (2)	164 (2)
O5—H5O···O4ii	0.83 (2)	1.83 (2)	2.663 (3)	178 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.83 (2)	2.14 (2)	2.948 (2)	164 (2)
O5—H5O⋯O4ii	0.83 (2)	1.83 (2)	2.663 (3)	178 (3)

Symmetry codes: (i) ; (ii) .