N-(3-Nitro-phen-yl)maleamic acid.

In the title compound, C(10)H(8)N(2)O(5), the mol-ecule is slightly distorted from planarity. The mol-ecular structure is stabilized by two intra-molecular hydrogen bonds. The first is a short O-H⋯O hydrogen bond (H⋯O distance = 1.57 Å) within the maleamic acid unit and the second is a C-H⋯O hydrogen bond (H⋯O distance = 2.24 Å) which connects the amide group with the benzene ring. The nitro group is twisted by 6.2 (2)° out of the plane of the benzene ring. The crystal structure manifests a variety of hydrogen bonding. The packing is dominated by a strong inter-molecular N-H⋯O inter-action which links the mol-ecules into chains running along the b axis. The chains within a plane are further assembled by three additional types of inter-molecular C-H⋯O hydrogen bonds to form a sheet parallel to the (01) plane.

Related literature

For studies on the effect of ring- and side-chain substitutions on the crystal structures of amides, see: Gowda, Tokarčík, Kožíšek et al. (2010 ▶); Gowda et al. (2010a ▶,b ▶); Prasad et al. (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H8N2O5

M = 236.18

Monoclinic,

a = 7.9965 (2) Å

b = 14.0253 (3) Å

c = 9.1026 (2) Å

β = 100.147 (3)°

V = 1004.92 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 295 K

0.57 × 0.33 × 0.28 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.926, T max = 0.971

17136 measured reflections

1793 independent reflections

1544 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.097

S = 1.08

1793 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022245/ds2039sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022245/ds2039Isup2.hkl

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

C10H8N2O5	F(000) = 488
Mr = 236.18	Dx = 1.561 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10218 reflections
a = 7.9965 (2) Å	θ = 2.3–29.4°
b = 14.0253 (3) Å	µ = 0.13 mm−1
c = 9.1026 (2) Å	T = 295 K
β = 100.147 (3)°	Prism, light brown
V = 1004.92 (4) Å3	0.57 × 0.33 × 0.28 mm
Z = 4

Oxford Diffraction Gemini R CCD diffractometer	1793 independent reflections
graphite	1544 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.023
ω scans	θmax = 25.1°, θmin = 2.6°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.926, Tmax = 0.971	k = −16→16
17136 measured reflections	l = −10→10

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0618P)2 + 0.1002P] where P = (Fo2 + 2Fc2)/3
1793 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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	0.30465 (16)	0.37499 (8)	0.57539 (15)	0.0361 (3)
C2	0.44044 (17)	0.38197 (9)	0.70806 (15)	0.0406 (3)
H2	0.4755	0.3245	0.7543	0.049*
C3	0.51952 (16)	0.45956 (10)	0.77048 (15)	0.0418 (3)
H3	0.5991	0.4471	0.8559	0.05*
C4	0.50454 (17)	0.56183 (10)	0.72945 (15)	0.0421 (3)
C5	0.13141 (15)	0.25342 (9)	0.41799 (14)	0.0342 (3)
C6	0.02666 (15)	0.31456 (9)	0.32224 (14)	0.0365 (3)
H6	0.0378	0.3804	0.3312	0.044*
C7	−0.09413 (16)	0.27380 (9)	0.21369 (13)	0.0357 (3)
C8	−0.11652 (17)	0.17731 (9)	0.19464 (16)	0.0422 (3)
H8	−0.1995	0.1528	0.1196	0.051*
C9	−0.01165 (19)	0.11799 (9)	0.29057 (17)	0.0476 (4)
H9	−0.0236	0.0522	0.2806	0.057*
C10	0.11119 (17)	0.15542 (9)	0.40145 (15)	0.0417 (3)
H10	0.181	0.1146	0.4656	0.05*
N1	0.25906 (14)	0.28534 (7)	0.53544 (12)	0.0389 (3)
H1N	0.3151	0.2413	0.5885	0.047*
N2	−0.20553 (14)	0.33698 (8)	0.11149 (12)	0.0442 (3)
O1	0.23643 (13)	0.44532 (6)	0.50694 (11)	0.0487 (3)
O2	0.38964 (13)	0.59058 (7)	0.61814 (12)	0.0547 (3)
H2A	0.3292	0.5383	0.5739	0.082*
O3	0.60038 (15)	0.61868 (8)	0.80038 (13)	0.0649 (3)
O4	−0.17942 (14)	0.42253 (7)	0.11665 (12)	0.0596 (3)
O5	−0.32118 (15)	0.30062 (8)	0.02350 (14)	0.0752 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0377 (7)	0.0306 (7)	0.0363 (7)	0.0005 (5)	−0.0039 (6)	0.0012 (5)
C2	0.0439 (7)	0.0332 (7)	0.0393 (7)	0.0036 (5)	−0.0078 (6)	0.0031 (5)
C3	0.0418 (7)	0.0415 (8)	0.0355 (7)	0.0014 (5)	−0.0115 (6)	−0.0003 (6)
C4	0.0467 (8)	0.0376 (7)	0.0381 (7)	−0.0022 (6)	−0.0034 (6)	−0.0044 (6)
C5	0.0359 (7)	0.0313 (7)	0.0326 (7)	−0.0003 (5)	−0.0018 (5)	−0.0013 (5)
C6	0.0406 (7)	0.0278 (6)	0.0373 (7)	−0.0016 (5)	−0.0035 (6)	−0.0011 (5)
C7	0.0372 (7)	0.0336 (7)	0.0334 (7)	0.0013 (5)	−0.0014 (5)	0.0014 (5)
C8	0.0431 (7)	0.0354 (7)	0.0429 (7)	−0.0039 (5)	−0.0069 (6)	−0.0052 (5)
C9	0.0559 (9)	0.0260 (7)	0.0547 (9)	−0.0017 (6)	−0.0071 (7)	−0.0031 (6)
C10	0.0452 (7)	0.0310 (7)	0.0441 (7)	0.0027 (5)	−0.0050 (6)	0.0023 (6)
N1	0.0424 (6)	0.0290 (5)	0.0388 (6)	0.0021 (4)	−0.0106 (5)	0.0024 (4)
N2	0.0475 (7)	0.0373 (7)	0.0413 (6)	0.0004 (5)	−0.0100 (5)	0.0006 (5)
O1	0.0556 (6)	0.0307 (5)	0.0493 (6)	0.0003 (4)	−0.0201 (5)	0.0031 (4)
O2	0.0659 (7)	0.0326 (6)	0.0549 (6)	−0.0029 (4)	−0.0190 (5)	0.0035 (4)
O3	0.0759 (8)	0.0444 (6)	0.0630 (7)	−0.0147 (5)	−0.0195 (6)	−0.0104 (5)
O4	0.0713 (7)	0.0326 (6)	0.0637 (7)	−0.0011 (5)	−0.0194 (5)	0.0051 (5)
O5	0.0769 (8)	0.0490 (7)	0.0778 (8)	−0.0031 (6)	−0.0463 (7)	0.0003 (6)

C1—O1	1.2406 (15)	C6—H6	0.93
C1—N1	1.3414 (16)	C7—C8	1.3721 (18)
C1—C2	1.4782 (19)	C7—N2	1.4670 (16)
C2—C3	1.3343 (19)	C8—C9	1.378 (2)
C2—H2	0.93	C8—H8	0.93
C3—C4	1.4817 (19)	C9—C10	1.3820 (19)
C3—H3	0.93	C9—H9	0.93
C4—O3	1.2106 (17)	C10—H10	0.93
C4—O2	1.3059 (17)	N1—H1N	0.86
C5—C10	1.3890 (18)	N2—O4	1.2174 (15)
C5—C6	1.3925 (17)	N2—O5	1.2231 (15)
C5—N1	1.4145 (16)	O2—H2A	0.93
C6—C7	1.3784 (17)
O1—C1—N1	122.32 (12)	C8—C7—N2	117.68 (11)
O1—C1—C2	123.53 (11)	C6—C7—N2	118.33 (11)
N1—C1—C2	114.14 (10)	C7—C8—C9	117.64 (12)
C3—C2—C1	128.80 (12)	C7—C8—H8	121.2
C3—C2—H2	115.6	C9—C8—H8	121.2
C1—C2—H2	115.6	C8—C9—C10	120.55 (12)
C2—C3—C4	132.14 (13)	C8—C9—H9	119.7
C2—C3—H3	113.9	C10—C9—H9	119.7
C4—C3—H3	113.9	C9—C10—C5	120.61 (12)
O3—C4—O2	120.21 (13)	C9—C10—H10	119.7
O3—C4—C3	119.18 (13)	C5—C10—H10	119.7
O2—C4—C3	120.60 (12)	C1—N1—C5	128.83 (11)
C10—C5—C6	119.72 (12)	C1—N1—H1N	115.6
C10—C5—N1	116.73 (11)	C5—N1—H1N	115.6
C6—C5—N1	123.54 (11)	O4—N2—O5	122.75 (11)
C7—C6—C5	117.49 (12)	O4—N2—C7	119.35 (10)
C7—C6—H6	121.3	O5—N2—C7	117.90 (11)
C5—C6—H6	121.3	C4—O2—H2A	109.5
C8—C7—C6	123.99 (12)
O1—C1—C2—C3	−4.7 (2)	C8—C9—C10—C5	−0.1 (2)
N1—C1—C2—C3	176.01 (13)	C6—C5—C10—C9	0.2 (2)
C1—C2—C3—C4	−1.9 (3)	N1—C5—C10—C9	179.35 (12)
C2—C3—C4—O3	−175.18 (15)	O1—C1—N1—C5	−1.3 (2)
C2—C3—C4—O2	4.8 (2)	C2—C1—N1—C5	177.97 (11)
C10—C5—C6—C7	−0.04 (18)	C10—C5—N1—C1	179.91 (12)
N1—C5—C6—C7	−179.15 (11)	C6—C5—N1—C1	−1.0 (2)
C5—C6—C7—C8	−0.15 (19)	C8—C7—N2—O4	−173.53 (12)
C5—C6—C7—N2	−179.87 (11)	C6—C7—N2—O4	6.21 (18)
C6—C7—C8—C9	0.2 (2)	C8—C7—N2—O5	6.09 (18)
N2—C7—C8—C9	179.91 (12)	C6—C7—N2—O5	−174.17 (12)
C7—C8—C9—C10	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.93	1.57	2.4978 (13)	176
C6—H6···O1	0.93	2.24	2.8302 (15)	121
N1—H1N···O3i	0.86	2.05	2.8929 (14)	167
C10—H10···O3i	0.93	2.51	3.2781 (17)	140
C3—H3···O5ii	0.93	2.57	3.2959 (17)	135
C9—H9···O4iii	0.93	2.51	3.1793 (17)	129
C8—H8···O2iii	0.93	2.57	3.4877 (17)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.93	1.57	2.4978 (13)	176
C6—H6⋯O1	0.93	2.24	2.8302 (15)	121
N1—H1N⋯O3i	0.86	2.05	2.8929 (14)	167
C10—H10⋯O3i	0.93	2.51	3.2781 (17)	140
C3—H3⋯O5ii	0.93	2.57	3.2959 (17)	135
C9—H9⋯O4iii	0.93	2.51	3.1793 (17)	129
C8—H8⋯O2iii	0.93	2.57	3.4877 (17)	170

Symmetry codes: (i) ; (ii) ; (iii) .