N-Phenyl-maleamic acid.

The two independent mol-ecules in the title compound (systematic name: 4-amino-4-oxobut-2-enoic acid), C(10)H(9)NO(3), are both essentially planar (r.m.s. deviations = 0.05 and 0.06 Å). In both mol-ecules, the -OH group forms an intra-molecular hydrogen bond to the amide O atom. Adjacent mol-ecules are linked by N-H⋯O hydrogen bonds into a flat ribbon that runs along the a axis of the monoclinic unit cell.

Related literature

For the crystal structures of other substituted N-(phen­yl)maleamic acids, see, for example: Gonzalez-Rodriguez et al. (1986 ▶); Home et al. (1991 ▶); Lynch & McClenaghan (2002 ▶); Parvez et al. (2004a ▶,b ▶); Prasad et al. (2002a ▶,b ▶); Santos-Sánchez et al. (2007 ▶); Wardell et al. (2005 ▶).

Experimental

Crystal data

C10H9NO3

M = 191.18

Monoclinic,

a = 12.7505 (4) Å

b = 10.5849 (5) Å

c = 14.1918 (6) Å

β = 116.299 (3)°

V = 1717.1 (1) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.24 × 0.06 × 0.06 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

11493 measured reflections

3925 independent reflections

2256 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.208

S = 1.02

3925 reflections

269 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.96 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014627/tk2436sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014627/tk2436Isup2.hkl

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

C10H9NO3	F(000) = 800
Mr = 191.18	Dx = 1.479 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1202 reflections
a = 12.7505 (4) Å	θ = 2.6–27.4°
b = 10.5849 (5) Å	µ = 0.11 mm−1
c = 14.1918 (6) Å	T = 100 K
β = 116.299 (3)°	Prism, colorless
V = 1717.1 (1) Å3	0.24 × 0.06 × 0.06 mm
Z = 8

Bruker SMART APEX diffractometer	2256 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
graphite	θmax = 27.5°, θmin = 1.8°
ω scans	h = −16→16
11493 measured reflections	k = −13→13
3925 independent reflections	l = −14→18

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.1139P)2] where P = (Fo2 + 2Fc2)/3
3925 reflections	(Δ/σ)max = 0.001
269 parameters	Δρmax = 0.96 e Å−3
4 restraints	Δρmin = −0.36 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.41604 (16)	0.86211 (19)	0.61750 (16)	0.0173 (5)
O2	0.41080 (17)	0.6545 (2)	0.62972 (17)	0.0167 (5)
H2O	0.449 (3)	0.590 (3)	0.627 (3)	0.058 (14)*
O3	0.53761 (17)	0.4779 (2)	0.62899 (16)	0.0187 (5)
O4	0.91395 (17)	0.5468 (2)	0.60999 (17)	0.0216 (5)
O5	0.91031 (17)	0.75293 (19)	0.62870 (17)	0.0164 (5)
H5O	0.946 (3)	0.820 (2)	0.625 (3)	0.028 (10)*
O6	1.03470 (16)	0.93320 (19)	0.62520 (16)	0.0187 (5)
N1	0.7136 (2)	0.4490 (2)	0.62704 (18)	0.0122 (5)
H1N	0.771 (2)	0.492 (3)	0.623 (2)	0.019 (8)*
N2	1.2093 (2)	0.9624 (2)	0.62037 (19)	0.0149 (6)
H2N	1.2657 (19)	0.923 (3)	0.611 (2)	0.020 (8)*
C1	0.4591 (2)	0.7584 (3)	0.6178 (2)	0.0123 (6)
C2	0.5691 (2)	0.7538 (3)	0.6046 (2)	0.0109 (6)
H2	0.5933	0.8336	0.5906	0.013*
C3	0.6396 (2)	0.6584 (3)	0.6087 (2)	0.0157 (6)
H3	0.7079	0.6811	0.6018	0.019*
C4	0.6250 (2)	0.5224 (3)	0.6227 (2)	0.0135 (6)
C5	0.7229 (2)	0.3155 (3)	0.6348 (2)	0.0130 (6)
C6	0.8169 (2)	0.2612 (3)	0.6232 (2)	0.0118 (6)
H6	0.8710	0.3139	0.6125	0.014*
C7	0.8311 (2)	0.1321 (3)	0.6272 (2)	0.0164 (6)
H7	0.8945	0.0957	0.6188	0.020*
C8	0.7521 (2)	0.0547 (3)	0.6436 (2)	0.0149 (6)
H8	0.7609	−0.0345	0.6450	0.018*
C9	0.6615 (2)	0.1075 (3)	0.6576 (2)	0.0171 (6)
H9	0.6086	0.0544	0.6697	0.020*
C10	0.6463 (2)	0.2388 (3)	0.6541 (2)	0.0136 (6)
H10	0.5843	0.2749	0.6648	0.016*
C11	0.9577 (2)	0.6509 (3)	0.6128 (2)	0.0145 (6)
C12	1.0671 (2)	0.6566 (3)	0.5988 (2)	0.0171 (6)
H12	1.0910	0.5773	0.5836	0.021*
C13	1.1380 (2)	0.7531 (3)	0.6038 (2)	0.0095 (6)
H13	1.2070	0.7313	0.5977	0.011*
C14	1.1215 (2)	0.8896 (3)	0.6177 (2)	0.0140 (6)
C15	1.2203 (2)	1.0966 (3)	0.6289 (2)	0.0130 (6)
C16	1.3130 (2)	1.1490 (3)	0.6154 (2)	0.0169 (7)
H16	1.3645	1.0961	0.6012	0.020*
C17	1.3298 (2)	1.2781 (3)	0.6228 (2)	0.0163 (6)
H17	1.3934	1.3136	0.6143	0.020*
C18	1.2542 (2)	1.3569 (3)	0.6427 (2)	0.0165 (6)
H18	1.2659	1.4458	0.6471	0.020*
C19	1.1619 (2)	1.3044 (3)	0.6560 (2)	0.0147 (6)
H19	1.1097	1.3576	0.6689	0.018*
C20	1.1457 (2)	1.1746 (3)	0.6504 (2)	0.0147 (6)
H20	1.0835	1.1388	0.6612	0.018*

	U11	U22	U33	U12	U13	U23
O1	0.0154 (10)	0.0149 (12)	0.0241 (12)	0.0036 (8)	0.0111 (9)	−0.0025 (9)
O2	0.0143 (10)	0.0118 (12)	0.0283 (12)	0.0004 (9)	0.0133 (9)	0.0026 (9)
O3	0.0165 (10)	0.0144 (12)	0.0298 (12)	−0.0003 (8)	0.0145 (9)	0.0015 (9)
O4	0.0195 (10)	0.0149 (12)	0.0335 (13)	−0.0042 (9)	0.0145 (10)	−0.0003 (9)
O5	0.0150 (10)	0.0108 (12)	0.0280 (13)	−0.0026 (8)	0.0138 (9)	0.0000 (9)
O6	0.0176 (10)	0.0126 (12)	0.0322 (13)	−0.0003 (9)	0.0166 (9)	−0.0029 (9)
N1	0.0159 (12)	0.0072 (13)	0.0159 (12)	−0.0001 (10)	0.0091 (10)	0.0012 (10)
N2	0.0145 (12)	0.0157 (14)	0.0175 (13)	0.0013 (10)	0.0097 (10)	0.0010 (10)
C1	0.0106 (13)	0.0144 (16)	0.0125 (15)	0.0004 (11)	0.0057 (11)	−0.0015 (11)
C2	0.0111 (13)	0.0083 (15)	0.0136 (14)	−0.0008 (10)	0.0057 (11)	−0.0022 (11)
C3	0.0166 (13)	0.0157 (17)	0.0185 (15)	−0.0007 (12)	0.0112 (12)	−0.0009 (12)
C4	0.0135 (13)	0.0150 (16)	0.0128 (14)	0.0017 (11)	0.0067 (11)	−0.0012 (11)
C5	0.0149 (13)	0.0136 (15)	0.0106 (14)	0.0022 (12)	0.0056 (11)	0.0007 (12)
C6	0.0127 (13)	0.0119 (15)	0.0128 (14)	−0.0023 (11)	0.0075 (11)	0.0004 (11)
C7	0.0161 (13)	0.0162 (17)	0.0165 (15)	0.0017 (12)	0.0068 (12)	−0.0009 (12)
C8	0.0231 (14)	0.0050 (14)	0.0177 (15)	−0.0012 (11)	0.0101 (12)	−0.0002 (11)
C9	0.0166 (13)	0.0175 (17)	0.0171 (15)	−0.0020 (12)	0.0075 (12)	0.0044 (12)
C10	0.0094 (12)	0.0195 (17)	0.0122 (15)	0.0029 (11)	0.0049 (11)	0.0005 (12)
C11	0.0151 (13)	0.0139 (16)	0.0159 (15)	0.0000 (12)	0.0082 (12)	0.0018 (12)
C12	0.0197 (14)	0.0182 (17)	0.0175 (15)	0.0032 (12)	0.0119 (12)	0.0005 (12)
C13	0.0114 (12)	0.0100 (14)	0.0075 (13)	0.0000 (10)	0.0044 (10)	−0.0009 (10)
C14	0.0176 (13)	0.0158 (16)	0.0091 (14)	0.0013 (12)	0.0064 (11)	0.0009 (11)
C15	0.0176 (13)	0.0107 (15)	0.0084 (13)	0.0042 (11)	0.0037 (11)	0.0025 (11)
C16	0.0171 (14)	0.0180 (17)	0.0167 (15)	0.0033 (12)	0.0083 (12)	0.0000 (12)
C17	0.0105 (13)	0.0211 (17)	0.0164 (15)	−0.0028 (12)	0.0051 (11)	0.0027 (13)
C18	0.0173 (14)	0.0139 (16)	0.0154 (15)	−0.0052 (12)	0.0046 (12)	−0.0002 (12)
C19	0.0135 (13)	0.0141 (16)	0.0155 (15)	−0.0006 (12)	0.0057 (11)	−0.0011 (12)
C20	0.0159 (13)	0.0149 (15)	0.0136 (15)	0.0020 (12)	0.0069 (11)	0.0005 (12)

O1—C1	1.227 (3)	C7—C8	1.395 (4)
O2—C1	1.307 (3)	C7—H7	0.9500
O2—H2O	0.846 (10)	C8—C9	1.375 (4)
O3—C4	1.249 (3)	C8—H8	0.9500
O4—C11	1.227 (3)	C9—C10	1.401 (4)
O5—C11	1.305 (3)	C9—H9	0.9500
O5—H5O	0.857 (10)	C10—H10	0.9500
O6—C14	1.247 (3)	C11—C12	1.495 (4)
N1—C4	1.350 (3)	C12—C13	1.344 (4)
N1—C5	1.419 (4)	C12—H12	0.9500
N1—H1N	0.879 (10)	C13—C14	1.486 (4)
N2—C14	1.345 (4)	C13—H13	0.9500
N2—C15	1.427 (4)	C15—C20	1.391 (4)
N2—H2N	0.886 (10)	C15—C16	1.394 (4)
C1—C2	1.496 (4)	C16—C17	1.379 (4)
C2—C3	1.335 (4)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.394 (4)
C3—C4	1.476 (4)	C17—H17	0.9500
C3—H3	0.9500	C18—C19	1.389 (4)
C5—C10	1.387 (4)	C18—H18	0.9500
C5—C6	1.403 (4)	C19—C20	1.387 (4)
C6—C7	1.377 (4)	C19—H19	0.9500
C6—H6	0.9500	C20—H20	0.9500
C1—O2—H2O	111 (3)	C10—C9—H9	119.7
C11—O5—H5O	112 (2)	C5—C10—C9	119.3 (3)
C4—N1—C5	128.0 (2)	C5—C10—H10	120.3
C4—N1—H1N	114 (2)	C9—C10—H10	120.3
C5—N1—H1N	118 (2)	O4—C11—O5	120.7 (2)
C14—N2—C15	128.4 (2)	O4—C11—C12	118.0 (3)
C14—N2—H2N	117 (2)	O5—C11—C12	121.3 (3)
C15—N2—H2N	115 (2)	C13—C12—C11	132.0 (3)
O1—C1—O2	121.2 (2)	C13—C12—H12	114.0
O1—C1—C2	118.1 (2)	C11—C12—H12	114.0
O2—C1—C2	120.7 (2)	C12—C13—C14	127.9 (2)
C3—C2—C1	132.0 (3)	C12—C13—H13	116.0
C3—C2—H2	114.0	C14—C13—H13	116.0
C1—C2—H2	114.0	O6—C14—N2	123.0 (3)
C2—C3—C4	128.4 (3)	O6—C14—C13	123.6 (3)
C2—C3—H3	115.8	N2—C14—C13	113.4 (2)
C4—C3—H3	115.8	C20—C15—C16	119.9 (3)
O3—C4—N1	122.3 (3)	C20—C15—N2	123.9 (3)
O3—C4—C3	123.1 (3)	C16—C15—N2	116.2 (2)
N1—C4—C3	114.5 (2)	C17—C16—C15	119.7 (3)
C10—C5—C6	119.8 (3)	C17—C16—H16	120.1
C10—C5—N1	123.8 (2)	C15—C16—H16	120.1
C6—C5—N1	116.4 (2)	C16—C17—C18	120.7 (3)
C7—C6—C5	120.3 (3)	C16—C17—H17	119.6
C7—C6—H6	119.8	C18—C17—H17	119.6
C5—C6—H6	119.8	C19—C18—C17	119.4 (3)
C6—C7—C8	119.9 (3)	C19—C18—H18	120.3
C6—C7—H7	120.0	C17—C18—H18	120.3
C8—C7—H7	120.0	C20—C19—C18	120.2 (3)
C9—C8—C7	120.0 (3)	C20—C19—H19	119.9
C9—C8—H8	120.0	C18—C19—H19	119.9
C7—C8—H8	120.0	C19—C20—C15	120.1 (3)
C8—C9—C10	120.6 (3)	C19—C20—H20	120.0
C8—C9—H9	119.7	C15—C20—H20	120.0
O1—C1—C2—C3	174.8 (3)	O4—C11—C12—C13	−175.7 (3)
O2—C1—C2—C3	−5.1 (5)	O5—C11—C12—C13	3.6 (5)
C1—C2—C3—C4	3.8 (5)	C11—C12—C13—C14	−5.2 (5)
C5—N1—C4—O3	2.6 (4)	C15—N2—C14—O6	−1.8 (5)
C5—N1—C4—C3	−176.7 (3)	C15—N2—C14—C13	177.6 (2)
C2—C3—C4—O3	2.7 (5)	C12—C13—C14—O6	−1.1 (5)
C2—C3—C4—N1	−178.0 (3)	C12—C13—C14—N2	179.4 (3)
C4—N1—C5—C10	−9.5 (4)	C14—N2—C15—C20	9.1 (4)
C4—N1—C5—C6	171.4 (3)	C14—N2—C15—C16	−171.5 (3)
C10—C5—C6—C7	2.3 (4)	C20—C15—C16—C17	−0.4 (4)
N1—C5—C6—C7	−178.5 (2)	N2—C15—C16—C17	−179.8 (2)
C5—C6—C7—C8	−0.4 (4)	C15—C16—C17—C18	−0.6 (4)
C6—C7—C8—C9	−1.2 (4)	C16—C17—C18—C19	0.5 (4)
C7—C8—C9—C10	0.9 (4)	C17—C18—C19—C20	0.5 (4)
C6—C5—C10—C9	−2.5 (4)	C18—C19—C20—C15	−1.5 (4)
N1—C5—C10—C9	178.4 (3)	C16—C15—C20—C19	1.5 (4)
C8—C9—C10—C5	0.9 (4)	N2—C15—C20—C19	−179.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O3	0.85 (1)	1.63 (1)	2.475 (3)	172 (4)
O5—H5o···O6	0.86 (1)	1.65 (1)	2.496 (3)	170 (3)
N1—H1n···O4	0.88 (1)	2.00 (1)	2.864 (3)	166 (3)
N2—H2n···O1i	0.89 (1)	1.99 (1)	2.859 (3)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2o⋯O3	0.85 (1)	1.63 (1)	2.475 (3)	172 (4)
O5—H5o⋯O6	0.86 (1)	1.65 (1)	2.496 (3)	170 (3)
N1—H1n⋯O4	0.88 (1)	2.00 (1)	2.864 (3)	166 (3)
N2—H2n⋯O1i	0.89 (1)	1.99 (1)	2.859 (3)	167 (3)

Symmetry code: (i) .