N-(4-Methyl-2-nitro-phen-yl)succinamic acid.

In the title compound, C(11)H(12)N(2)O(5), the conformation of the N-H bond in the amide segment is syn to the ortho-nitro group in the benzene ring. The amide C=O and the carboxyl C=O of the acid segment are syn to each other and both are anti to the H atoms on the adjacent -CH(2) groups. Furthermore, the C=O and O-H bonds of the acid group are in syn positions with respect to each other. The dihedral angle between the benzene ring and the amide group is 36.1 (1)°. The amide H atom shows bifurcated intra-molecular hydrogen bonding with an O atom of the ortho-nitro group and an inter-molecular hydrogen bond with the carbonyl O atom of another mol-ecule. In the crystal, the N-H⋯O(C) hydrogen bonds generate a chain running along the [100] direction. Inversion dimers are formed via a pair of O-H⋯O(C) interactions, that form an eight-membered hydrogen-bonded ring involving the carboxyl group.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (1999 ▶, 2006 ▶); Chaithanya et al. (2012 ▶). For N-(ar­yl)-methane­sulfon­amides, see: Gowda et al. (2007 ▶). For N-chloro­aryl­amides, see: Jyothi & Gowda (2004 ▶). For N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C11H12N2O5

M = 252.23

Triclinic,

a = 4.8531 (7) Å

b = 11.015 (2) Å

c = 11.787 (2) Å

α = 69.59 (1)°

β = 78.77 (1)°

γ = 83.62 (2)°

V = 578.59 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.40 × 0.22 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.955, T max = 0.986

3557 measured reflections

2314 independent reflections

1900 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.119

S = 1.05

2314 reflections

170 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007258/kp2388sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007258/kp2388Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007258/kp2388Isup3.cml

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

C11H12N2O5	Z = 2
Mr = 252.23	F(000) = 264
Triclinic, P1	Dx = 1.448 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8531 (7) Å	Cell parameters from 1681 reflections
b = 11.015 (2) Å	θ = 3.1–27.8°
c = 11.787 (2) Å	µ = 0.12 mm−1
α = 69.59 (1)°	T = 293 K
β = 78.77 (1)°	Needle, yellow
γ = 83.62 (2)°	0.40 × 0.22 × 0.12 mm
V = 578.59 (17) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2314 independent reflections
Radiation source: fine-focus sealed tube	1900 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −5→6
Tmin = 0.955, Tmax = 0.986	k = −13→13
3557 measured reflections	l = −14→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0471P)2 + 0.2987P] where P = (Fo2 + 2Fc2)/3
2314 reflections	(Δ/σ)max = 0.006
170 parameters	Δρmax = 0.23 e Å−3
2 restraints	Δρmin = −0.22 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.0723 (3)	0.37100 (17)	0.38806 (15)	0.0344 (4)
C2	0.2308 (4)	0.40404 (17)	0.26912 (16)	0.0351 (4)
C3	0.1566 (4)	0.51144 (18)	0.17381 (17)	0.0423 (4)
H3	0.2650	0.5299	0.0960	0.051*
C4	−0.0749 (4)	0.59120 (18)	0.19244 (18)	0.0439 (5)
C5	−0.2278 (4)	0.56114 (19)	0.31041 (19)	0.0463 (5)
H5	−0.3823	0.6146	0.3257	0.056*
C6	−0.1571 (4)	0.45416 (19)	0.40568 (17)	0.0429 (4)
H6	−0.2652	0.4373	0.4834	0.052*
C7	−0.0488 (4)	0.18197 (18)	0.57398 (16)	0.0385 (4)
C8	0.0872 (4)	0.0644 (2)	0.65902 (18)	0.0474 (5)
H8A	0.1761	0.0914	0.7127	0.057*
H8B	0.2330	0.0268	0.6106	0.057*
C9	−0.1198 (4)	−0.03824 (19)	0.73683 (18)	0.0459 (5)
H9A	−0.2447	−0.0471	0.6855	0.055*
H9B	−0.0163	−0.1206	0.7655	0.055*
C10	−0.2937 (4)	−0.01095 (18)	0.84541 (16)	0.0392 (4)
C11	−0.1609 (5)	0.7055 (2)	0.0885 (2)	0.0627 (6)
H11A	−0.3126	0.6828	0.0593	0.075*
H11B	−0.0037	0.7291	0.0228	0.075*
H11C	−0.2211	0.7774	0.1169	0.075*
N1	0.1378 (3)	0.26122 (16)	0.48575 (14)	0.0402 (4)
H1N	0.308 (3)	0.237 (2)	0.485 (2)	0.048*
N2	0.4831 (3)	0.32707 (15)	0.23859 (14)	0.0422 (4)
O1	−0.3032 (3)	0.20209 (15)	0.58421 (14)	0.0599 (5)
O2	−0.2182 (3)	0.05642 (16)	0.89554 (14)	0.0591 (4)
O3	−0.5284 (3)	−0.07162 (16)	0.88538 (13)	0.0533 (4)
H3O	−0.606 (5)	−0.063 (3)	0.9514 (18)	0.064*
O4	0.5972 (4)	0.35547 (18)	0.13202 (15)	0.0802 (6)
O5	0.5750 (3)	0.23852 (15)	0.31947 (14)	0.0579 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0299 (8)	0.0388 (9)	0.0306 (8)	−0.0020 (7)	−0.0043 (7)	−0.0073 (7)
C2	0.0333 (9)	0.0362 (9)	0.0355 (9)	−0.0031 (7)	−0.0022 (7)	−0.0129 (7)
C3	0.0483 (11)	0.0408 (10)	0.0327 (9)	−0.0069 (8)	−0.0023 (8)	−0.0070 (8)
C4	0.0483 (11)	0.0377 (10)	0.0411 (10)	−0.0042 (8)	−0.0115 (8)	−0.0048 (8)
C5	0.0402 (10)	0.0427 (10)	0.0497 (11)	0.0075 (8)	−0.0062 (9)	−0.0114 (9)
C6	0.0361 (10)	0.0485 (11)	0.0363 (9)	0.0034 (8)	0.0006 (8)	−0.0096 (8)
C7	0.0297 (9)	0.0478 (10)	0.0306 (8)	0.0016 (7)	−0.0045 (7)	−0.0053 (8)
C8	0.0317 (9)	0.0548 (12)	0.0379 (10)	0.0051 (8)	−0.0017 (7)	0.0021 (9)
C9	0.0420 (10)	0.0419 (10)	0.0411 (10)	0.0059 (8)	−0.0029 (8)	−0.0026 (8)
C10	0.0329 (9)	0.0389 (9)	0.0347 (9)	0.0001 (7)	−0.0070 (7)	0.0016 (8)
C11	0.0699 (15)	0.0489 (12)	0.0536 (13)	0.0014 (11)	−0.0153 (11)	0.0036 (10)
N1	0.0255 (7)	0.0483 (9)	0.0344 (8)	0.0038 (6)	−0.0019 (6)	−0.0017 (7)
N2	0.0416 (9)	0.0422 (9)	0.0398 (8)	−0.0020 (7)	0.0036 (7)	−0.0154 (7)
O1	0.0268 (7)	0.0661 (10)	0.0599 (9)	0.0007 (6)	−0.0064 (6)	0.0112 (7)
O2	0.0535 (9)	0.0721 (10)	0.0508 (9)	−0.0233 (8)	0.0059 (7)	−0.0212 (8)
O3	0.0425 (8)	0.0697 (10)	0.0441 (8)	−0.0172 (7)	0.0014 (6)	−0.0150 (7)
O4	0.0901 (13)	0.0767 (12)	0.0462 (9)	0.0173 (10)	0.0240 (9)	−0.0119 (8)
O5	0.0500 (8)	0.0649 (10)	0.0499 (8)	0.0201 (7)	−0.0043 (7)	−0.0172 (8)

C1—C6	1.392 (2)	C8—C9	1.516 (3)
C1—N1	1.405 (2)	C8—H8A	0.9700
C1—C2	1.406 (2)	C8—H8B	0.9700
C2—C3	1.388 (2)	C9—C10	1.494 (3)
C2—N2	1.469 (2)	C9—H9A	0.9700
C3—C4	1.379 (3)	C9—H9B	0.9700
C3—H3	0.9300	C10—O2	1.219 (2)
C4—C5	1.388 (3)	C10—O3	1.306 (2)
C4—C11	1.506 (3)	C11—H11A	0.9600
C5—C6	1.380 (3)	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
C6—H6	0.9300	N1—H1N	0.840 (15)
C7—O1	1.220 (2)	N2—O4	1.215 (2)
C7—N1	1.356 (2)	N2—O5	1.216 (2)
C7—C8	1.510 (2)	O3—H3O	0.828 (17)
C6—C1—N1	120.65 (16)	C9—C8—H8B	109.0
C6—C1—C2	116.32 (16)	H8A—C8—H8B	107.8
N1—C1—C2	123.04 (16)	C10—C9—C8	114.65 (18)
C3—C2—C1	121.65 (16)	C10—C9—H9A	108.6
C3—C2—N2	116.31 (15)	C8—C9—H9A	108.6
C1—C2—N2	122.05 (15)	C10—C9—H9B	108.6
C4—C3—C2	121.19 (17)	C8—C9—H9B	108.6
C4—C3—H3	119.4	H9A—C9—H9B	107.6
C2—C3—H3	119.4	O2—C10—O3	123.11 (18)
C3—C4—C5	117.44 (17)	O2—C10—C9	123.32 (17)
C3—C4—C11	121.31 (19)	O3—C10—C9	113.48 (18)
C5—C4—C11	121.24 (19)	C4—C11—H11A	109.5
C6—C5—C4	121.87 (18)	C4—C11—H11B	109.5
C6—C5—H5	119.1	H11A—C11—H11B	109.5
C4—C5—H5	119.1	C4—C11—H11C	109.5
C5—C6—C1	121.50 (17)	H11A—C11—H11C	109.5
C5—C6—H6	119.3	H11B—C11—H11C	109.5
C1—C6—H6	119.3	C7—N1—C1	126.29 (15)
O1—C7—N1	123.78 (16)	C7—N1—H1N	116.4 (15)
O1—C7—C8	122.49 (16)	C1—N1—H1N	116.8 (15)
N1—C7—C8	113.73 (15)	O4—N2—O5	121.64 (17)
C7—C8—C9	113.01 (16)	O4—N2—C2	118.41 (17)
C7—C8—H8A	109.0	O5—N2—C2	119.95 (15)
C9—C8—H8A	109.0	C10—O3—H3O	110.5 (18)
C7—C8—H8B	109.0
C6—C1—C2—C3	−2.0 (3)	O1—C7—C8—C9	13.1 (3)
N1—C1—C2—C3	178.40 (17)	N1—C7—C8—C9	−166.36 (18)
C6—C1—C2—N2	178.13 (16)	C7—C8—C9—C10	−79.0 (2)
N1—C1—C2—N2	−1.5 (3)	C8—C9—C10—O2	−25.8 (3)
C1—C2—C3—C4	0.7 (3)	C8—C9—C10—O3	157.49 (16)
N2—C2—C3—C4	−179.39 (17)	O1—C7—N1—C1	−5.4 (3)
C2—C3—C4—C5	1.0 (3)	C8—C7—N1—C1	174.13 (18)
C2—C3—C4—C11	−178.18 (19)	C6—C1—N1—C7	39.0 (3)
C3—C4—C5—C6	−1.4 (3)	C2—C1—N1—C7	−141.4 (2)
C11—C4—C5—C6	177.7 (2)	C3—C2—N2—O4	−5.4 (3)
C4—C5—C6—C1	0.1 (3)	C1—C2—N2—O4	174.42 (19)
N1—C1—C6—C5	−178.82 (18)	C3—C2—N2—O5	173.52 (17)
C2—C1—C6—C5	1.6 (3)	C1—C2—N2—O5	−6.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O5	0.84 (2)	2.11 (2)	2.648 (2)	121 (2)
N1—H1N···O1i	0.84 (2)	2.34 (2)	3.072 (2)	146 (2)
O3—H3O···O2ii	0.83 (2)	1.86 (2)	2.688 (2)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O5	0.84 (2)	2.11 (2)	2.648 (2)	121 (2)
N1—H1N⋯O1i	0.84 (2)	2.34 (2)	3.072 (2)	146 (2)
O3—H3O⋯O2ii	0.83 (2)	1.86 (2)	2.688 (2)	176 (3)

Symmetry codes: (i) ; (ii) .