(2Z)-4-[(2-Hy-droxy-phen-yl)carbamo-yl]prop-2-enoic acid.

In the title compound, C(10)H(9)NO(4), the 2-hy-droxy-anilinic and the 4-oxobut-2-enoic acid groups are almost planar, with r.m.s. deviations of 0.0086 and 0.0262 Å, respectively. The dihedral angle between the two groups is 6.65 (1)°. Intra-molecular N-H⋯O, C-H⋯O and O-H⋯O hydrogen bonds form S(5), S(6) and S(7) ring motifs. In the crystal, the mol-ecules are dimerized due to C-H⋯O and O-H⋯O inter-molecular hydrogen bonds, with R(2) (2)(8) ring motifs. The dimers are inter-linked into polymeric chains along [010] with R(4) (3)(13) ring motifs by C-H⋯O, N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For background and a related structure, see: Shah et al. (2008 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H9NO4

M = 207.18

Orthorhombic,

a = 6.7873 (3) Å

b = 10.6855 (4) Å

c = 12.8442 (4) Å

V = 931.54 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.32 × 0.25 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.968, T max = 0.978

4118 measured reflections

997 independent reflections

944 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.082

S = 1.09

997 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045496/bq2250sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045496/bq2250Isup2.hkl

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

C10H9NO4	F(000) = 432
Mr = 207.18	Dx = 1.477 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 944 reflections
a = 6.7873 (3) Å	θ = 3.2–25.2°
b = 10.6855 (4) Å	µ = 0.12 mm−1
c = 12.8442 (4) Å	T = 296 K
V = 931.54 (6) Å3	Prism, yellow
Z = 4	0.32 × 0.25 × 0.24 mm

Bruker Kappa APEXII CCD diffractometer	997 independent reflections
Radiation source: fine-focus sealed tube	944 reflections with I > 2σ(I)
graphite	Rint = 0.015
Detector resolution: 8.2 pixels mm-1	θmax = 25.2°, θmin = 3.2°
ω scans	h = −7→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
Tmin = 0.968, Tmax = 0.978	l = −15→14
4118 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.050P)2 + 0.1393P] where P = (Fo2 + 2Fc2)/3
997 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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
O1	0.0644 (3)	−0.02680 (12)	0.57792 (9)	0.0460 (5)
O2	0.0945 (3)	0.39908 (12)	0.45571 (10)	0.0498 (5)
O3	0.0839 (4)	0.62508 (12)	0.50201 (11)	0.0565 (6)
O4	0.0659 (3)	0.73178 (12)	0.64703 (12)	0.0519 (5)
N1	0.0940 (3)	0.21180 (13)	0.53692 (11)	0.0339 (4)
C1	0.0933 (3)	0.12928 (16)	0.45057 (14)	0.0311 (5)
C2	0.0788 (3)	0.00188 (16)	0.47494 (13)	0.0333 (5)
C3	0.0808 (3)	−0.08600 (17)	0.39600 (15)	0.0397 (6)
C4	0.0939 (4)	−0.04766 (19)	0.29330 (16)	0.0416 (6)
C5	0.1054 (3)	0.07754 (19)	0.26907 (14)	0.0403 (6)
C6	0.1071 (3)	0.16658 (18)	0.34720 (14)	0.0358 (5)
C7	0.0946 (3)	0.33779 (16)	0.53732 (14)	0.0312 (5)
C8	0.0967 (3)	0.39436 (16)	0.64192 (14)	0.0341 (5)
C9	0.0918 (3)	0.51549 (17)	0.66740 (14)	0.0366 (5)
C10	0.0796 (3)	0.63080 (16)	0.60326 (15)	0.0384 (6)
H1	0.09395	0.17669	0.59717	0.0407*
H1A	0.06683	−0.10302	0.58522	0.0552*
H3	0.07345	−0.17079	0.41187	0.0476*
H3A	0.09210	0.55176	0.48367	0.0677*
H4	0.09499	−0.10695	0.24030	0.0499*
H5	0.11194	0.10243	0.19978	0.0483*
H6	0.11753	0.25104	0.33063	0.0430*
H8	0.10215	0.33850	0.69736	0.0409*
H9	0.09700	0.53039	0.73868	0.0439*

	U11	U22	U33	U12	U13	U23
O1	0.0805 (11)	0.0226 (6)	0.0350 (7)	0.0016 (8)	−0.0057 (7)	0.0025 (5)
O2	0.0934 (12)	0.0237 (6)	0.0322 (7)	0.0007 (8)	−0.0019 (10)	0.0017 (5)
O3	0.1077 (14)	0.0221 (7)	0.0396 (8)	0.0033 (10)	−0.0012 (10)	0.0015 (5)
O4	0.0801 (11)	0.0239 (6)	0.0518 (9)	−0.0005 (8)	−0.0008 (9)	−0.0067 (6)
N1	0.0494 (9)	0.0225 (7)	0.0299 (7)	0.0008 (8)	−0.0004 (9)	0.0006 (5)
C1	0.0335 (9)	0.0249 (9)	0.0350 (9)	0.0011 (8)	−0.0023 (10)	−0.0039 (7)
C2	0.0402 (9)	0.0262 (9)	0.0335 (9)	0.0014 (9)	−0.0038 (9)	0.0005 (7)
C3	0.0480 (11)	0.0256 (9)	0.0455 (11)	−0.0017 (10)	−0.0046 (11)	−0.0065 (8)
C4	0.0467 (12)	0.0376 (10)	0.0404 (10)	−0.0027 (10)	−0.0003 (10)	−0.0120 (8)
C5	0.0449 (12)	0.0440 (11)	0.0319 (9)	−0.0015 (11)	−0.0008 (10)	−0.0026 (8)
C6	0.0426 (10)	0.0302 (9)	0.0347 (9)	0.0011 (9)	0.0009 (10)	0.0018 (8)
C7	0.0374 (9)	0.0213 (8)	0.0348 (9)	0.0002 (8)	−0.0006 (10)	0.0014 (7)
C8	0.0446 (11)	0.0257 (8)	0.0319 (9)	−0.0006 (10)	0.0016 (10)	0.0040 (7)
C9	0.0466 (10)	0.0314 (9)	0.0318 (9)	−0.0016 (10)	0.0028 (10)	−0.0031 (7)
C10	0.0481 (12)	0.0245 (9)	0.0427 (10)	−0.0014 (10)	−0.0009 (11)	−0.0025 (8)

O1—C2	1.361 (2)	C3—C4	1.384 (3)
O2—C7	1.236 (2)	C4—C5	1.376 (3)
O3—C10	1.302 (2)	C5—C6	1.383 (3)
O4—C10	1.220 (2)	C7—C8	1.473 (3)
O1—H1A	0.8200	C8—C9	1.336 (2)
O3—H3A	0.8200	C9—C10	1.485 (3)
N1—C1	1.417 (2)	C3—H3	0.9300
N1—C7	1.346 (2)	C4—H4	0.9300
N1—H1	0.8600	C5—H5	0.9300
C1—C2	1.400 (2)	C6—H6	0.9300
C1—C6	1.389 (3)	C8—H8	0.9300
C2—C3	1.382 (3)	C9—H9	0.9300
O1···O4i	2.7282 (18)	C7···C1viii	3.424 (3)
O1···N1	2.6111 (19)	C8···C6ix	3.528 (3)
O1···C5ii	3.368 (3)	C8···C1ix	3.583 (3)
O2···C10	3.120 (2)	C8···C6viii	3.389 (3)
O2···C6	2.850 (2)	C8···C5viii	3.538 (3)
O2···O3	2.4881 (18)	C8···O4vi	3.404 (2)
O3···O2	2.4881 (18)	C9···C5viii	3.543 (3)
O3···C3iii	3.374 (2)	C9···C4viii	3.434 (3)
O3···C7	3.104 (2)	C9···C4ix	3.462 (3)
O4···C8iv	3.404 (2)	C9···C3ix	3.500 (3)
O4···C5v	3.404 (3)	C10···C3viii	3.419 (3)
O4···O1iii	2.7282 (18)	C10···O2	3.120 (2)
O1···H1	2.2000	C10···C3ix	3.435 (3)
O1···H5ii	2.8200	C4···H6xii	3.0400
O1···H9vi	2.6700	C6···H4vii	3.0000
O2···H6	2.2600	C7···H3A	2.3900
O2···H4vii	2.8300	C7···H6	2.8200
O2···H3A	1.6700	C8···H3A	2.6400
O3···H3iii	2.4700	C10···H1Aiii	2.8600
O4···H5v	2.8900	H1···O1	2.2000
O4···H1Aiii	1.9400	H1···H8	2.1600
O4···H8iv	2.5700	H1A···O4i	1.9400
N1···O1	2.6111 (19)	H1A···C10i	2.8600
C1···C7viii	3.407 (3)	H1A···H3	2.3400
C1···C7ix	3.424 (3)	H3···O3i	2.4700
C1···C8viii	3.583 (3)	H3···H1A	2.3400
C3···O3i	3.374 (2)	H3A···O2	1.6700
C3···C9viii	3.500 (3)	H3A···C7	2.3900
C3···C10viii	3.435 (3)	H3A···C8	2.6400
C3···C10ix	3.419 (3)	H4···O2xii	2.8300
C4···C9viii	3.462 (3)	H4···C6xii	3.0000
C4···C9ix	3.434 (3)	H4···H6xii	2.2800
C5···C8ix	3.538 (3)	H5···O1x	2.8200
C5···O1x	3.368 (3)	H5···O4xi	2.8900
C5···O4xi	3.404 (3)	H6···O2	2.2600
C5···C9ix	3.543 (3)	H6···C7	2.8200
C6···C8ix	3.389 (3)	H6···C4vii	3.0400
C6···O2	2.850 (2)	H6···H4vii	2.2800
C6···C8viii	3.528 (3)	H8···H1	2.1600
C7···C1ix	3.407 (3)	H8···O4vi	2.5700
C7···O3	3.104 (2)	H9···O1iv	2.6700
C2—O1—H1A	109.00	C7—C8—C9	128.38 (17)
C10—O3—H3A	109.00	C8—C9—C10	132.05 (17)
C1—N1—C7	128.71 (15)	O3—C10—C9	120.93 (15)
C1—N1—H1	116.00	O4—C10—C9	118.85 (17)
C7—N1—H1	116.00	O3—C10—O4	120.22 (17)
N1—C1—C6	124.70 (16)	C2—C3—H3	120.00
C2—C1—C6	119.82 (16)	C4—C3—H3	120.00
N1—C1—C2	115.48 (15)	C3—C4—H4	120.00
C1—C2—C3	119.73 (16)	C5—C4—H4	120.00
O1—C2—C1	116.18 (15)	C4—C5—H5	120.00
O1—C2—C3	124.10 (16)	C6—C5—H5	120.00
C2—C3—C4	119.91 (17)	C1—C6—H6	120.00
C3—C4—C5	120.47 (18)	C5—C6—H6	120.00
C4—C5—C6	120.35 (17)	C7—C8—H8	116.00
C1—C6—C5	119.70 (17)	C9—C8—H8	116.00
O2—C7—N1	121.78 (16)	C8—C9—H9	114.00
O2—C7—C8	123.78 (16)	C10—C9—H9	114.00
N1—C7—C8	114.44 (15)
C7—N1—C1—C2	−175.7 (2)	O1—C2—C3—C4	179.3 (2)
C7—N1—C1—C6	4.8 (4)	C1—C2—C3—C4	−1.0 (3)
C1—N1—C7—O2	0.0 (4)	C2—C3—C4—C5	0.1 (4)
C1—N1—C7—C8	−179.6 (2)	C3—C4—C5—C6	1.0 (4)
N1—C1—C2—O1	0.9 (3)	C4—C5—C6—C1	−1.2 (3)
N1—C1—C2—C3	−178.76 (19)	O2—C7—C8—C9	2.6 (4)
C6—C1—C2—O1	−179.54 (19)	N1—C7—C8—C9	−177.8 (2)
C6—C1—C2—C3	0.8 (3)	C7—C8—C9—C10	1.2 (4)
N1—C1—C6—C5	179.9 (2)	C8—C9—C10—O3	−4.4 (4)
C2—C1—C6—C5	0.3 (3)	C8—C9—C10—O4	175.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.20	2.6111 (19)	109
O1—H1A···O4i	0.82	1.94	2.7282 (18)	162
O3—H3A···O2	0.82	1.67	2.4881 (18)	175
C3—H3···O3i	0.93	2.47	3.374 (2)	164
C6—H6···O2	0.93	2.26	2.850 (2)	121
C8—H8···O4vi	0.93	2.57	3.404 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	2.20	2.6111 (19)	109
O1—H1A⋯O4i	0.82	1.94	2.7282 (18)	162
O3—H3A⋯O2	0.82	1.67	2.4881 (18)	175
C3—H3⋯O3i	0.93	2.47	3.374 (2)	164
C6—H6⋯O2	0.93	2.26	2.850 (2)	121
C8—H8⋯O4ii	0.93	2.57	3.404 (2)	150

Symmetry codes: (i) ; (ii) .