Methyl (2Z)-3-[(4-nitro-phen-yl)carbamo-yl]prop-2-enoate.

In the title compound, C(11)H(10)N(2)O(5), the amide group is nearly coplanar and the ester group approximately perpendicular to the vinyl C-HC=CH-C group [dihedral angles of 5.0 (2) and 88.89 (5)°, respectively]. This results in a short intra-molecular O =C⋯O=C contact of 2.7201 (17) Å between the amide O atom and the ester carbonyl C atom. The prop-2-enamide fragment and the nitro group make dihedral angles of 20.42 (6) and 13.54 (17)°, respectively, with the benzene ring. An intra-molecular C-H⋯O inter-action between the benzene ring and the amide group generates an S(6) ring motif. Inter-molecular C-H⋯O and N-H⋯O hydrogen bonds complete R(2) (2)(11) ring motifs and join mol-ecules into [100] chains.

Related literature

For crystal structures of N-substituted maleamic acids, see: Lo & Ng (2009 ▶); Wardell et al. (2005 ▶). For the synthesis of (4-[(4-nitro­phen­yl)amino]-4-oxobut-2-enoic acid, see: Shahid et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H10N2O5

M = 250.21

Triclinic,

a = 6.8382 (2) Å

b = 7.7497 (2) Å

c = 11.8277 (5) Å

α = 97.805 (2)°

β = 92.119 (2)°

γ = 114.425 (1)°

V = 562.39 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.35 × 0.26 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.897, T max = 0.922

8150 measured reflections

2021 independent reflections

1754 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.097

S = 1.08

2021 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.15 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/S1600536810050956/gk2328sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050956/gk2328Isup2.hkl

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

C11H10N2O5	Z = 2
Mr = 250.21	F(000) = 260
Triclinic, P1	Dx = 1.478 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8382 (2) Å	Cell parameters from 1754 reflections
b = 7.7497 (2) Å	θ = 3.2–25.3°
c = 11.8277 (5) Å	µ = 0.12 mm−1
α = 97.805 (2)°	T = 296 K
β = 92.119 (2)°	Prism, light green
γ = 114.425 (1)°	0.35 × 0.26 × 0.24 mm
V = 562.39 (3) Å3

Bruker Kappa APEXII CCD diffractometer	2021 independent reflections
Radiation source: fine-focus sealed tube	1754 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 3.2°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.897, Tmax = 0.922	l = −14→14
8150 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0475P)2 + 0.101P] where P = (Fo2 + 2Fc2)/3
2021 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.15 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	0.14198 (15)	0.84577 (15)	0.41306 (9)	0.0545 (3)
O2	0.10967 (16)	1.06232 (16)	0.31587 (9)	0.0568 (4)
O3	0.34399 (14)	0.84813 (15)	0.17681 (8)	0.0518 (3)
O4	0.5882 (2)	0.46462 (19)	−0.33243 (11)	0.0766 (5)
O5	0.92706 (19)	0.55754 (18)	−0.28426 (12)	0.0743 (5)
N1	0.70053 (17)	0.91905 (18)	0.16737 (10)	0.0484 (4)
N2	0.7481 (2)	0.54311 (18)	−0.26298 (12)	0.0567 (5)
C1	−0.0900 (3)	0.7351 (3)	0.39699 (17)	0.0670 (6)
C2	0.2191 (2)	1.0025 (2)	0.36544 (11)	0.0433 (4)
C3	0.4580 (2)	1.1052 (2)	0.39010 (12)	0.0467 (4)
C4	0.5981 (2)	1.0757 (2)	0.32569 (12)	0.0467 (4)
C5	0.5316 (2)	0.9364 (2)	0.21728 (12)	0.0422 (4)
C6	0.6983 (2)	0.8127 (2)	0.06154 (12)	0.0429 (4)
C7	0.5276 (2)	0.7463 (2)	−0.02453 (12)	0.0461 (5)
C8	0.5423 (2)	0.6543 (2)	−0.12949 (12)	0.0476 (4)
C9	0.7270 (2)	0.6289 (2)	−0.14903 (13)	0.0466 (4)
C10	0.8956 (2)	0.6898 (2)	−0.06399 (14)	0.0542 (5)
C11	0.8810 (2)	0.7806 (2)	0.04099 (14)	0.0537 (5)
H1	0.82501	0.98188	0.20614	0.0581*
H1A	−0.15939	0.81926	0.41485	0.1005*
H1B	−0.13094	0.64057	0.44679	0.1005*
H1C	−0.13336	0.67204	0.31868	0.1005*
H3	0.51277	1.19737	0.45606	0.0560*
H4	0.74467	1.14518	0.34934	0.0560*
H7	0.40353	0.76407	−0.01099	0.0553*
H8	0.42826	0.60944	−0.18708	0.0571*
H11	1.01806	0.66940	−0.07773	0.0651*
H12	0.99377	0.82118	0.09894	0.0644*

	U11	U22	U33	U12	U13	U23
O1	0.0396 (5)	0.0613 (7)	0.0579 (6)	0.0170 (5)	0.0001 (4)	0.0103 (5)
O2	0.0425 (6)	0.0708 (7)	0.0618 (7)	0.0301 (5)	−0.0034 (5)	0.0087 (5)
O3	0.0288 (5)	0.0674 (7)	0.0542 (6)	0.0187 (5)	−0.0003 (4)	0.0006 (5)
O4	0.0659 (8)	0.0831 (9)	0.0654 (8)	0.0238 (7)	0.0026 (6)	−0.0111 (7)
O5	0.0610 (7)	0.0715 (8)	0.0904 (9)	0.0299 (6)	0.0290 (6)	0.0013 (7)
N1	0.0273 (5)	0.0678 (8)	0.0473 (7)	0.0184 (5)	−0.0002 (4)	0.0069 (6)
N2	0.0524 (8)	0.0481 (7)	0.0670 (9)	0.0186 (6)	0.0162 (7)	0.0070 (6)
C1	0.0427 (9)	0.0682 (11)	0.0792 (12)	0.0157 (8)	0.0089 (8)	0.0018 (9)
C2	0.0382 (7)	0.0559 (8)	0.0360 (7)	0.0230 (6)	0.0007 (5)	−0.0013 (6)
C3	0.0389 (7)	0.0549 (8)	0.0425 (7)	0.0184 (6)	−0.0043 (5)	0.0032 (6)
C4	0.0312 (7)	0.0570 (8)	0.0477 (8)	0.0145 (6)	−0.0022 (5)	0.0103 (6)
C5	0.0318 (7)	0.0542 (8)	0.0432 (7)	0.0194 (6)	0.0025 (5)	0.0134 (6)
C6	0.0301 (6)	0.0509 (8)	0.0476 (8)	0.0154 (6)	0.0051 (5)	0.0133 (6)
C7	0.0318 (7)	0.0601 (9)	0.0507 (8)	0.0225 (6)	0.0045 (5)	0.0130 (7)
C8	0.0369 (7)	0.0543 (8)	0.0500 (8)	0.0175 (6)	0.0005 (6)	0.0100 (7)
C9	0.0399 (7)	0.0435 (8)	0.0553 (8)	0.0151 (6)	0.0115 (6)	0.0110 (6)
C10	0.0334 (7)	0.0630 (9)	0.0693 (10)	0.0233 (7)	0.0100 (7)	0.0101 (8)
C11	0.0306 (7)	0.0705 (10)	0.0599 (9)	0.0217 (7)	0.0005 (6)	0.0103 (7)

O1—C1	1.448 (2)	C6—C7	1.392 (2)
O1—C2	1.3224 (18)	C7—C8	1.374 (2)
O2—C2	1.2029 (19)	C8—C9	1.379 (2)
O3—C5	1.2177 (18)	C9—C10	1.378 (2)
O4—N2	1.220 (2)	C10—C11	1.370 (2)
O5—N2	1.221 (2)	C1—H1A	0.9600
N1—C5	1.363 (2)	C1—H1B	0.9600
N1—C6	1.3980 (18)	C1—H1C	0.9600
N2—C9	1.459 (2)	C3—H3	0.9300
N1—H1	0.8600	C4—H4	0.9300
C2—C3	1.488 (2)	C7—H7	0.9300
C3—C4	1.318 (2)	C8—H8	0.9300
C4—C5	1.480 (2)	C10—H11	0.9300
C6—C11	1.395 (2)	C11—H12	0.9300
O1···O3	3.1615 (14)	C1···C2ix	3.595 (2)
O1···O5i	3.1218 (17)	C2···O3	2.7201 (17)
O1···C3ii	3.3877 (18)	C2···C1ix	3.595 (2)
O1···C4ii	3.3565 (18)	C3···O1ii	3.3877 (18)
O2···C9iii	3.1785 (18)	C3···C3ii	3.400 (2)
O2···O3	3.1114 (16)	C4···O1ii	3.3565 (18)
O2···N1iv	2.9467 (17)	C5···O4i	3.363 (2)
O2···N2iii	2.9652 (17)	C6···C8i	3.523 (2)
O2···O5iii	3.1282 (18)	C7···O3	2.8983 (17)
O3···O1	3.1615 (14)	C8···C6i	3.523 (2)
O3···C11iv	3.3020 (19)	C9···O2iii	3.1785 (18)
O3···C7	2.8983 (17)	C11···C11vii	3.404 (2)
O3···O2	3.1114 (16)	C11···O3viii	3.3020 (19)
O3···C2	2.7201 (17)	C2···H1Aix	2.9000
O3···N2i	3.1522 (17)	C5···H7	2.7800
O4···C5i	3.363 (2)	H1···O2viii	2.1100
O4···C1v	3.116 (3)	H1···H4	2.2000
O5···O1i	3.1218 (17)	H1···H12	2.3100
O5···O2iii	3.1282 (18)	H1A···O2	2.4900
O5···C1i	3.089 (3)	H1A···O4v	2.8700
O1···H4ii	2.8700	H1A···C2ix	2.9000
O2···H1C	2.7900	H1C···O2	2.7900
O2···H1A	2.4900	H1C···O4v	2.8600
O2···H12iv	2.8300	H1C···O5i	2.6900
O2···H1iv	2.1100	H1C···H8v	2.5400
O2···H4iv	2.8500	H3···O4x	2.9000
O3···H12iv	2.4500	H4···O2viii	2.8500
O3···H7	2.3300	H4···H1	2.2000
O4···H1Av	2.8700	H4···O1ii	2.8700
O4···H1Cv	2.8600	H4···O5vii	2.7000
O4···H3vi	2.9000	H7···O3	2.3300
O4···H8	2.4600	H7···C5	2.7800
O5···H11	2.4400	H7···H11iv	2.4900
O5···H1Ci	2.6900	H8···O4	2.4600
O5···H4vii	2.7000	H8···H1Cv	2.5400
N1···O2viii	2.9467 (17)	H11···O5	2.4400
N2···O2iii	2.9652 (17)	H11···H7viii	2.4900
N2···O3i	3.1522 (17)	H12···O2viii	2.8300
C1···O4v	3.116 (3)	H12···O3viii	2.4500
C1···O5i	3.089 (3)	H12···H1	2.3100
C1—O1—C2	116.39 (13)	C8—C9—C10	121.14 (14)
C5—N1—C6	128.61 (13)	C9—C10—C11	119.34 (14)
O4—N2—O5	123.51 (15)	C6—C11—C10	120.46 (14)
O4—N2—C9	118.66 (14)	O1—C1—H1A	109.00
O5—N2—C9	117.81 (14)	O1—C1—H1B	109.00
C5—N1—H1	116.00	O1—C1—H1C	109.00
C6—N1—H1	116.00	H1A—C1—H1B	109.00
O2—C2—C3	124.08 (13)	H1A—C1—H1C	109.00
O1—C2—O2	124.52 (14)	H1B—C1—H1C	109.00
O1—C2—C3	111.18 (12)	C2—C3—H3	117.00
C2—C3—C4	125.07 (13)	C4—C3—H3	117.00
C3—C4—C5	122.68 (14)	C3—C4—H4	119.00
O3—C5—C4	122.79 (13)	C5—C4—H4	119.00
N1—C5—C4	113.42 (13)	C6—C7—H7	120.00
O3—C5—N1	123.79 (13)	C8—C7—H7	120.00
C7—C6—C11	119.37 (13)	C7—C8—H8	120.00
N1—C6—C7	122.98 (14)	C9—C8—H8	120.00
N1—C6—C11	117.58 (13)	C9—C10—H11	120.00
C6—C7—C8	119.98 (14)	C11—C10—H11	120.00
C7—C8—C9	119.67 (14)	C6—C11—H12	120.00
N2—C9—C10	119.33 (14)	C10—C11—H12	120.00
N2—C9—C8	119.49 (13)
C1—O1—C2—O2	4.0 (2)	C3—C4—C5—O3	4.5 (2)
C1—O1—C2—C3	178.82 (13)	C3—C4—C5—N1	−176.21 (14)
C5—N1—C6—C7	17.9 (2)	N1—C6—C7—C8	175.40 (14)
C5—N1—C6—C11	−165.10 (14)	C11—C6—C7—C8	−1.6 (2)
C6—N1—C5—O3	4.5 (2)	N1—C6—C11—C10	−175.18 (13)
C6—N1—C5—C4	−174.85 (13)	C7—C6—C11—C10	2.0 (2)
O5—N2—C9—C10	−12.0 (2)	C6—C7—C8—C9	−0.2 (2)
O5—N2—C9—C8	165.51 (14)	C7—C8—C9—N2	−175.78 (13)
O4—N2—C9—C10	169.43 (14)	C7—C8—C9—C10	1.7 (2)
O4—N2—C9—C8	−13.0 (2)	N2—C9—C10—C11	176.17 (13)
O1—C2—C3—C4	90.27 (17)	C8—C9—C10—C11	−1.3 (2)
O2—C2—C3—C4	−94.83 (19)	C9—C10—C11—C6	−0.5 (2)
C2—C3—C4—C5	1.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2viii	0.86	2.11	2.9467 (17)	164
C7—H7···O3	0.93	2.33	2.8983 (17)	119
C11—H12···O3viii	0.93	2.45	3.3020 (19)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.11	2.9467 (17)	164
C7—H7⋯O3	0.93	2.33	2.8983 (17)	119
C11—H12⋯O3i	0.93	2.45	3.3020 (19)	152

Symmetry code: (i) .