(Z)-3-(Benzyl-carbamo-yl)prop-2-enoic acid.

The title compound, C(11)H(11)NO(3), was synthesized by the reaction of maleic andydride and phenyl-methanamine. The mol-ecular conformation is stabilized by by an intra-molecular O-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, forming a chain along the b axis.

Related literature

For related structures, see Gowda et al. (2009a ▶,b ▶,c ▶); Prasad et al. (2002 ▶).

Experimental

Crystal data

C11H11NO3

M = 205.21

Monoclinic,

a = 10.651 (2) Å

b = 12.601 (3) Å

c = 8.3130 (17) Å

β = 108.44 (3)°

V = 1058.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.972, T max = 0.991

2018 measured reflections

1913 independent reflections

1013 reflections with I > 2σ(I)

R int = 0.022

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.175

S = 1.00

1913 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100609X/kj2163sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100609X/kj2163Isup2.hkl

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

C11H11NO3	F(000) = 432
Mr = 205.21	Dx = 1.288 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.651 (2) Å	θ = 9–12°
b = 12.601 (3) Å	µ = 0.10 mm−1
c = 8.3130 (17) Å	T = 298 K
β = 108.44 (3)°	Block, colorless
V = 1058.4 (4) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1013 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
graphite	θmax = 25.3°, θmin = 2.0°
ω/2θ scans	h = −12→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
Tmin = 0.972, Tmax = 0.991	l = −9→9
2018 measured reflections	3 standard reflections every 200 reflections
1913 independent reflections	intensity decay: 1%

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.175	w = 1/[σ2(Fo2) + (0.078P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1913 reflections	Δρmax = 0.17 e Å−3
137 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (5)

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
N	0.6963 (2)	0.4593 (2)	0.1087 (3)	0.0537 (7)
H0A	0.6678	0.5211	0.1242	0.064*
O1	0.6741 (2)	0.28274 (17)	0.1283 (3)	0.0636 (7)
C1	1.0039 (4)	0.3602 (3)	0.2253 (6)	0.0904 (14)
H1A	0.9678	0.2962	0.1767	0.108*
O2	0.3695 (2)	0.17148 (18)	0.3280 (3)	0.0750 (8)
C2	1.1254 (4)	0.3611 (4)	0.3536 (7)	0.1015 (16)
H2A	1.1693	0.2975	0.3903	0.122*
O3	0.5270 (2)	0.15868 (18)	0.2112 (3)	0.0669 (7)
H3B	0.5786	0.2005	0.1821	0.100*
C3	1.1799 (4)	0.4531 (4)	0.4250 (6)	0.0853 (13)
H3A	1.2611	0.4532	0.5106	0.102*
C4	1.1149 (4)	0.5457 (4)	0.3707 (6)	0.0871 (13)
H4A	1.1519	0.6097	0.4188	0.104*
C5	0.9942 (4)	0.5450 (3)	0.2443 (5)	0.0754 (11)
H5A	0.9505	0.6088	0.2085	0.090*
C6	0.9377 (3)	0.4525 (3)	0.1707 (4)	0.0547 (9)
C7	0.8043 (3)	0.4522 (3)	0.0365 (4)	0.0621 (10)
H7A	0.7989	0.5117	−0.0394	0.074*
H7B	0.7946	0.3876	−0.0296	0.074*
C8	0.6403 (3)	0.3750 (2)	0.1514 (4)	0.0491 (8)
C9	0.5356 (3)	0.3986 (3)	0.2282 (4)	0.0500 (8)
H9A	0.5219	0.4702	0.2440	0.060*
C10	0.4586 (3)	0.3320 (3)	0.2777 (4)	0.0522 (8)
H10A	0.3995	0.3648	0.3235	0.063*
C11	0.4498 (4)	0.2143 (3)	0.2731 (4)	0.0556 (9)

	U11	U22	U33	U12	U13	U23
N	0.0488 (16)	0.0458 (15)	0.0658 (18)	0.0025 (13)	0.0169 (14)	0.0026 (13)
O1	0.0654 (15)	0.0463 (13)	0.0842 (17)	0.0078 (12)	0.0306 (13)	−0.0028 (12)
C1	0.064 (2)	0.062 (3)	0.134 (4)	0.000 (2)	0.016 (3)	−0.001 (2)
O2	0.0792 (17)	0.0585 (15)	0.094 (2)	−0.0142 (14)	0.0373 (16)	0.0101 (14)
C2	0.068 (3)	0.083 (3)	0.141 (4)	0.014 (2)	0.014 (3)	0.025 (3)
O3	0.0856 (18)	0.0436 (13)	0.0764 (16)	−0.0009 (12)	0.0326 (15)	0.0007 (12)
C3	0.066 (3)	0.109 (4)	0.078 (3)	0.001 (3)	0.020 (2)	−0.001 (3)
C4	0.077 (3)	0.086 (3)	0.097 (3)	−0.011 (3)	0.025 (3)	−0.027 (3)
C5	0.070 (2)	0.061 (3)	0.088 (3)	0.002 (2)	0.014 (2)	−0.003 (2)
C6	0.0485 (19)	0.055 (2)	0.065 (2)	−0.0001 (17)	0.0250 (17)	0.0034 (18)
C7	0.059 (2)	0.066 (2)	0.067 (2)	−0.0028 (18)	0.0293 (19)	0.0036 (18)
C8	0.0486 (19)	0.0436 (18)	0.0496 (19)	0.0012 (16)	0.0075 (15)	−0.0011 (15)
C9	0.055 (2)	0.0375 (17)	0.057 (2)	0.0008 (15)	0.0162 (17)	−0.0012 (15)
C10	0.058 (2)	0.0462 (18)	0.054 (2)	0.0006 (17)	0.0205 (17)	0.0011 (16)
C11	0.061 (2)	0.0463 (19)	0.053 (2)	−0.0039 (19)	0.0084 (17)	0.0024 (17)

N—C8	1.320 (4)	C3—H3A	0.9300
N—C7	1.459 (4)	C4—C5	1.379 (5)
N—H0A	0.8600	C4—H4A	0.9300
O1—C8	1.250 (3)	C5—C6	1.365 (5)
C1—C6	1.361 (5)	C5—H5A	0.9300
C1—C2	1.392 (6)	C6—C7	1.503 (4)
C1—H1A	0.9300	C7—H7A	0.9700
O2—C11	1.216 (4)	C7—H7B	0.9700
C2—C3	1.347 (6)	C8—C9	1.480 (4)
C2—H2A	0.9300	C9—C10	1.327 (4)
O3—C11	1.304 (4)	C9—H9A	0.9300
O3—H3B	0.8501	C10—C11	1.485 (4)
C3—C4	1.360 (6)	C10—H10A	0.9300
C8—N—C7	122.9 (3)	C1—C6—C7	121.0 (3)
C8—N—H0A	118.5	C5—C6—C7	120.9 (3)
C7—N—H0A	118.5	N—C7—C6	112.2 (3)
C6—C1—C2	120.5 (4)	N—C7—H7A	109.2
C6—C1—H1A	119.8	C6—C7—H7A	109.2
C2—C1—H1A	119.8	N—C7—H7B	109.2
C3—C2—C1	120.7 (4)	C6—C7—H7B	109.2
C3—C2—H2A	119.6	H7A—C7—H7B	107.9
C1—C2—H2A	119.6	O1—C8—N	122.1 (3)
C11—O3—H3B	108.9	O1—C8—C9	123.1 (3)
C2—C3—C4	119.3 (4)	N—C8—C9	114.8 (3)
C2—C3—H3A	120.4	C10—C9—C8	129.1 (3)
C4—C3—H3A	120.4	C10—C9—H9A	115.5
C3—C4—C5	120.1 (4)	C8—C9—H9A	115.5
C3—C4—H4A	120.0	C9—C10—C11	131.6 (3)
C5—C4—H4A	120.0	C9—C10—H10A	114.2
C6—C5—C4	121.3 (4)	C11—C10—H10A	114.2
C6—C5—H5A	119.3	O2—C11—O3	121.0 (3)
C4—C5—H5A	119.3	O2—C11—C10	118.7 (3)
C1—C6—C5	118.1 (4)	O3—C11—C10	120.3 (3)
C6—C1—C2—C3	−0.4 (7)	C1—C6—C7—N	98.2 (4)
C1—C2—C3—C4	0.1 (7)	C5—C6—C7—N	−80.0 (4)
C2—C3—C4—C5	0.3 (7)	C7—N—C8—O1	−1.9 (5)
C3—C4—C5—C6	−0.3 (6)	C7—N—C8—C9	177.9 (3)
C2—C1—C6—C5	0.4 (6)	O1—C8—C9—C10	−3.0 (5)
C2—C1—C6—C7	−177.9 (4)	N—C8—C9—C10	177.2 (3)
C4—C5—C6—C1	−0.1 (6)	C8—C9—C10—C11	−0.3 (5)
C4—C5—C6—C7	178.2 (4)	C9—C10—C11—O2	179.7 (3)
C8—N—C7—C6	−89.9 (4)	C9—C10—C11—O3	−0.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O1	0.85	1.61	2.461 (3)	178
N—H0A···O2i	0.86	2.00	2.855 (3)	171
C9—H9A···O3i	0.93	2.48	3.413 (4)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯O1	0.85	1.61	2.461 (3)	178
N—H0A⋯O2i	0.86	2.00	2.855 (3)	171
C9—H9A⋯O3i	0.93	2.48	3.413 (4)	177

Symmetry code: (i) .