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

In the title compound, C(11)H(11)NO(5)S, the dihedral angle between the benzene ring and the amide group is 76.88 (6)°. In the crystal, N-H⋯O(S) and O-H⋯O hydrogen bonds connect the mol-ecules into hydrogen-bonded layers perpendicular to the a axis.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2001 ▶); Shahwar et al. (2012 ▶), of N-(aryl­sulfon­yl)-succinamic acids, see: Purandara et al. (2012 ▶), of N-(ar­yl)-methane­sulfonn class="Chemical">amides, see: Gowda et al. (2007 ▶) and of N-chloro­aryl­sulfonamides, see: Gowda & Ramachandra (1989 ▶); Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C11H11NO5S

M = 269.27

Monoclinic,

a = 10.2652 (6) Å

b = 11.9064 (7) Å

c = 10.2416 (6) Å

β = 108.403 (7)°

V = 1187.73 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.44 × 0.42 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.885, T max = 0.894

4608 measured reflections

2424 independent reflections

2144 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.086

S = 1.07

2424 reflections

171 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis n class="Disease">RED (Oxford Diffraction, 2009 ▶); 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/S1600536812032084/zl2493sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032084/zl2493Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032084/zl2493Isup3.cml

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

C11H11NO5S	F(000) = 560
Mr = 269.27	Dx = 1.506 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2735 reflections
a = 10.2652 (6) Å	θ = 3.0–27.8°
b = 11.9064 (7) Å	µ = 0.29 mm−1
c = 10.2416 (6) Å	T = 293 K
β = 108.403 (7)°	Prism, colourless
V = 1187.73 (12) Å3	0.44 × 0.42 × 0.40 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2424 independent reflections
Radiation source: fine-focus sealed tube	2144 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.010
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→12
Tmin = 0.885, Tmax = 0.894	k = −6→14
4608 measured reflections	l = −12→12

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.3604P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2424 reflections	Δρmax = 0.36 e Å−3
171 parameters	Δρmin = −0.29 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (2)

Experimental. 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	0.36379 (14)	0.75860 (12)	0.11249 (15)	0.0323 (3)
C2	0.45226 (16)	0.69418 (14)	0.21423 (16)	0.0408 (4)
H2	0.4187	0.6370	0.2566	0.049*
C3	0.59187 (17)	0.71591 (16)	0.25246 (17)	0.0463 (4)
H3	0.6519	0.6731	0.3216	0.056*
C4	0.64338 (16)	0.79985 (14)	0.18983 (18)	0.0431 (4)
C5	0.55266 (18)	0.86083 (15)	0.0852 (2)	0.0482 (4)
H5	0.5865	0.9161	0.0404	0.058*
C6	0.41309 (17)	0.84149 (14)	0.04582 (18)	0.0432 (4)
H6	0.3532	0.8835	−0.0243	0.052*
C7	0.13459 (13)	0.94544 (13)	0.14452 (14)	0.0315 (3)
C8	0.08229 (14)	1.00963 (12)	0.24353 (15)	0.0339 (3)
H8	−0.0104	1.0285	0.2148	0.041*
C9	0.15667 (15)	1.04155 (13)	0.36794 (15)	0.0364 (3)
H9	0.1136	1.0807	0.4214	0.044*
C10	0.30479 (15)	1.01820 (13)	0.42652 (14)	0.0343 (3)
C11	0.79430 (18)	0.8267 (2)	0.2343 (3)	0.0666 (6)
H11A	0.8436	0.7723	0.3007	0.100*
H11B	0.8093	0.9002	0.2746	0.100*
H11C	0.8263	0.8246	0.1558	0.100*
N1	0.13089 (12)	0.83006 (11)	0.15952 (12)	0.0317 (3)
H1N	0.1246 (18)	0.8042 (14)	0.2308 (15)	0.038*
O1	0.16042 (12)	0.63163 (9)	0.12040 (14)	0.0492 (3)
O2	0.12374 (12)	0.76432 (11)	−0.07348 (11)	0.0468 (3)
O3	0.16830 (11)	0.99099 (10)	0.05504 (11)	0.0421 (3)
O4	0.36494 (11)	0.95387 (10)	0.37140 (11)	0.0442 (3)
O5	0.36415 (12)	1.07342 (11)	0.53916 (12)	0.0492 (3)
H5O	0.456 (3)	1.060 (2)	0.571 (2)	0.074*
S1	0.18624 (3)	0.73748 (3)	0.06857 (4)	0.03364 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0310 (7)	0.0372 (8)	0.0306 (7)	−0.0021 (6)	0.0125 (6)	−0.0062 (6)
C2	0.0415 (8)	0.0442 (9)	0.0368 (8)	−0.0014 (7)	0.0126 (7)	0.0031 (7)
C3	0.0383 (8)	0.0549 (10)	0.0409 (9)	0.0062 (7)	0.0059 (7)	−0.0004 (7)
C4	0.0326 (8)	0.0456 (9)	0.0534 (10)	−0.0019 (7)	0.0168 (7)	−0.0155 (7)
C5	0.0415 (9)	0.0447 (9)	0.0656 (12)	−0.0033 (7)	0.0268 (8)	0.0035 (8)
C6	0.0381 (8)	0.0457 (9)	0.0482 (9)	0.0026 (7)	0.0170 (7)	0.0088 (7)
C7	0.0237 (6)	0.0401 (8)	0.0265 (7)	−0.0002 (5)	0.0020 (5)	−0.0001 (6)
C8	0.0276 (7)	0.0355 (7)	0.0374 (8)	0.0039 (6)	0.0082 (6)	0.0001 (6)
C9	0.0358 (7)	0.0366 (8)	0.0370 (8)	0.0045 (6)	0.0119 (6)	−0.0049 (6)
C10	0.0355 (7)	0.0351 (7)	0.0297 (7)	−0.0005 (6)	0.0064 (6)	−0.0034 (6)
C11	0.0335 (9)	0.0736 (14)	0.0916 (16)	−0.0064 (9)	0.0183 (10)	−0.0190 (12)
N1	0.0323 (6)	0.0375 (7)	0.0272 (6)	−0.0026 (5)	0.0121 (5)	−0.0023 (5)
O1	0.0494 (7)	0.0371 (6)	0.0666 (8)	−0.0124 (5)	0.0261 (6)	−0.0097 (5)
O2	0.0399 (6)	0.0664 (8)	0.0305 (6)	−0.0013 (5)	0.0060 (5)	−0.0148 (5)
O3	0.0444 (6)	0.0467 (7)	0.0363 (6)	0.0003 (5)	0.0143 (5)	0.0070 (5)
O4	0.0350 (6)	0.0494 (7)	0.0419 (6)	0.0057 (5)	0.0032 (5)	−0.0146 (5)
O5	0.0400 (6)	0.0629 (8)	0.0386 (6)	−0.0005 (6)	0.0037 (5)	−0.0203 (5)
S1	0.0305 (2)	0.0382 (2)	0.0325 (2)	−0.00642 (14)	0.01037 (15)	−0.00955 (14)

C1—C2	1.379 (2)	C8—C9	1.318 (2)
C1—C6	1.384 (2)	C8—H8	0.9300
C1—S1	1.7520 (14)	C9—C10	1.474 (2)
C2—C3	1.386 (2)	C9—H9	0.9300
C2—H2	0.9300	C10—O4	1.2274 (18)
C3—C4	1.380 (2)	C10—O5	1.3002 (17)
C3—H3	0.9300	C11—H11A	0.9600
C4—C5	1.383 (3)	C11—H11B	0.9600
C4—C11	1.505 (2)	C11—H11C	0.9600
C5—C6	1.380 (2)	N1—S1	1.6551 (12)
C5—H5	0.9300	N1—H1N	0.813 (13)
C6—H6	0.9300	O1—S1	1.4246 (12)
C7—O3	1.2059 (17)	O2—S1	1.4286 (12)
C7—N1	1.384 (2)	O5—H5O	0.91 (2)
C7—C8	1.498 (2)
C2—C1—C6	120.89 (14)	C7—C8—H8	117.3
C2—C1—S1	119.85 (12)	C8—C9—C10	123.19 (13)
C6—C1—S1	119.24 (12)	C8—C9—H9	118.4
C1—C2—C3	119.04 (15)	C10—C9—H9	118.4
C1—C2—H2	120.5	O4—C10—O5	124.10 (13)
C3—C2—H2	120.5	O4—C10—C9	122.31 (13)
C4—C3—C2	121.19 (15)	O5—C10—C9	113.58 (13)
C4—C3—H3	119.4	C4—C11—H11A	109.5
C2—C3—H3	119.4	C4—C11—H11B	109.5
C3—C4—C5	118.52 (14)	H11A—C11—H11B	109.5
C3—C4—C11	121.47 (17)	C4—C11—H11C	109.5
C5—C4—C11	120.01 (17)	H11A—C11—H11C	109.5
C6—C5—C4	121.46 (16)	H11B—C11—H11C	109.5
C6—C5—H5	119.3	C7—N1—S1	124.90 (10)
C4—C5—H5	119.3	C7—N1—H1N	119.2 (13)
C5—C6—C1	118.86 (15)	S1—N1—H1N	113.1 (13)
C5—C6—H6	120.6	C10—O5—H5O	111.8 (15)
C1—C6—H6	120.6	O1—S1—O2	120.05 (7)
O3—C7—N1	123.73 (14)	O1—S1—N1	104.01 (7)
O3—C7—C8	122.35 (14)	O2—S1—N1	107.49 (7)
N1—C7—C8	113.76 (12)	O1—S1—C1	109.40 (7)
C9—C8—C7	125.42 (13)	O2—S1—C1	109.01 (7)
C9—C8—H8	117.3	N1—S1—C1	105.91 (6)
C6—C1—C2—C3	2.1 (2)	C8—C9—C10—O4	−10.6 (3)
S1—C1—C2—C3	−176.73 (12)	C8—C9—C10—O5	168.24 (15)
C1—C2—C3—C4	−0.5 (3)	O3—C7—N1—S1	6.5 (2)
C2—C3—C4—C5	−1.4 (3)	C8—C7—N1—S1	−177.98 (9)
C2—C3—C4—C11	177.78 (16)	C7—N1—S1—O1	−179.73 (12)
C3—C4—C5—C6	1.9 (3)	C7—N1—S1—O2	−51.43 (13)
C11—C4—C5—C6	−177.29 (17)	C7—N1—S1—C1	64.99 (13)
C4—C5—C6—C1	−0.4 (3)	C2—C1—S1—O1	−16.74 (14)
C2—C1—C6—C5	−1.6 (2)	C6—C1—S1—O1	164.41 (12)
S1—C1—C6—C5	177.22 (13)	C2—C1—S1—O2	−149.80 (12)
O3—C7—C8—C9	−96.45 (19)	C6—C1—S1—O2	31.35 (14)
N1—C7—C8—C9	87.94 (18)	C2—C1—S1—N1	94.81 (13)
C7—C8—C9—C10	0.5 (3)	C6—C1—S1—N1	−84.04 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.81 (1)	2.17 (1)	2.9786 (16)	176 (2)
O5—H5O···O4ii	0.91 (2)	1.75 (2)	2.6589 (16)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.81 (1)	2.17 (1)	2.9786 (16)	176 (2)
O5—H5O⋯O4ii	0.91 (2)	1.75 (2)	2.6589 (16)	176 (2)

Symmetry codes: (i) ; (ii) .