2-(2-Nitro-anilino)benzoic acid.

In the title compound, C(13)H(10)N(2)O(4), the nitro N atom deviates by 0.031 (2) Å from the plane of the benzene ring to which it is attached. The aromatic rings are oriented at a dihedral angle of 50.6 (1)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, inversion dimers are formed by pairs of O-H⋯O inter-actions.

Related literature

For the use of the title compound as an inter­mediate in the synthesis pharmacologically important compounds, see: Kelleher et al. (2007 ▶). For the synthesis, see: Rewcastle et al. (1987 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H10N2O4

M = 258.23

Monoclinic,

a = 7.1840 (14) Å

b = 21.546 (4) Å

c = 7.9070 (16) Å

β = 101.62 (3)°

V = 1198.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

4704 measured reflections

2209 independent reflections

1437 reflections with I > 2σ(I)

R int = 0.046

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.158

S = 1.01

2209 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: SET4 (Enraf–Nonius, 1994 ▶); data reduction: MolEN (Harms & Wocadlo,1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811053529/im2343sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053529/im2343Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053529/im2343Isup3.cml

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

C13H10N2O4	F(000) = 536
Mr = 258.23	Dx = 1.431 Mg m−3
Monoclinic, P21/c	Melting point: 490 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.1840 (14) Å	Cell parameters from 25 reflections
b = 21.546 (4) Å	θ = 10–13°
c = 7.9070 (16) Å	µ = 0.11 mm−1
β = 101.62 (3)°	T = 293 K
V = 1198.8 (4) Å3	Block, yellow
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.046
Radiation source: fine-focus sealed tube	θmax = 25.4°, θmin = 1.9°
graphite	h = 0→8
ω/2θ scans	k = −25→25
4704 measured reflections	l = −9→9
2209 independent reflections	3 standard reflections every 200 reflections
1437 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.092P)2] where P = (Fo2 + 2Fc2)/3
2209 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.32 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
N1	0.3630 (3)	0.63169 (9)	0.8669 (2)	0.0512 (6)
H1A	0.2975	0.6083	0.7889	0.061*
O1	0.6904 (2)	0.49333 (8)	0.6877 (2)	0.0644 (6)
H1C	0.6478	0.4799	0.5906	0.097*
C1	0.5770 (4)	0.62113 (12)	1.1447 (3)	0.0525 (6)
H1B	0.5117	0.6527	1.1882	0.063*
O2	0.4326 (2)	0.55260 (8)	0.6238 (2)	0.0565 (5)
N2	−0.0301 (3)	0.66483 (11)	0.7232 (3)	0.0617 (6)
C2	0.7255 (4)	0.59204 (13)	1.2522 (3)	0.0584 (7)
H2A	0.7594	0.6040	1.3673	0.070*
O3	0.0167 (3)	0.61293 (10)	0.6871 (3)	0.0755 (6)
C3	0.8248 (4)	0.54511 (14)	1.1905 (3)	0.0604 (7)
H3A	0.9260	0.5257	1.2629	0.073*
C4	0.7721 (3)	0.52775 (12)	1.0218 (3)	0.0550 (7)
H4A	0.8376	0.4957	0.9809	0.066*
O4	−0.1970 (3)	0.68049 (12)	0.6926 (4)	0.1088 (9)
C5	0.6226 (3)	0.55667 (10)	0.9083 (3)	0.0437 (6)
C6	0.5225 (3)	0.60428 (11)	0.9718 (3)	0.0447 (6)
C7	0.5730 (3)	0.53451 (11)	0.7287 (3)	0.0469 (6)
C8	0.2996 (3)	0.69134 (11)	0.8744 (3)	0.0428 (6)
C9	0.1125 (3)	0.70950 (11)	0.8017 (3)	0.0461 (6)
C10	0.0547 (4)	0.77113 (13)	0.8017 (3)	0.0599 (7)
H10A	−0.0698	0.7817	0.7519	0.072*
C11	0.1794 (4)	0.81632 (13)	0.8742 (4)	0.0618 (7)
H11A	0.1414	0.8576	0.8723	0.074*
C12	0.3632 (4)	0.79945 (11)	0.9505 (3)	0.0537 (7)
H12A	0.4478	0.8296	1.0035	0.064*
C13	0.4222 (3)	0.73919 (11)	0.9492 (3)	0.0492 (6)
H13A	0.5473	0.7295	0.9993	0.059*

	U11	U22	U33	U12	U13	U23
N1	0.0457 (12)	0.0446 (12)	0.0561 (13)	0.0086 (10)	−0.0068 (9)	−0.0118 (9)
O1	0.0490 (11)	0.0629 (12)	0.0772 (13)	0.0150 (9)	0.0031 (9)	−0.0213 (9)
C1	0.0485 (14)	0.0528 (15)	0.0545 (15)	0.0053 (12)	0.0068 (11)	−0.0022 (12)
O2	0.0558 (11)	0.0512 (11)	0.0580 (10)	0.0111 (9)	0.0009 (8)	−0.0077 (8)
N2	0.0439 (13)	0.0625 (16)	0.0708 (15)	0.0036 (11)	−0.0069 (11)	0.0035 (12)
C2	0.0530 (15)	0.0641 (17)	0.0522 (15)	−0.0082 (14)	−0.0036 (12)	0.0016 (13)
O3	0.0606 (13)	0.0603 (13)	0.0932 (15)	−0.0053 (10)	−0.0141 (10)	−0.0106 (11)
C3	0.0407 (14)	0.0642 (18)	0.0697 (18)	0.0035 (12)	−0.0049 (13)	0.0077 (14)
C4	0.0385 (13)	0.0537 (16)	0.0705 (18)	0.0056 (12)	0.0051 (12)	0.0014 (12)
O4	0.0413 (12)	0.099 (2)	0.171 (3)	0.0063 (12)	−0.0146 (14)	−0.0119 (16)
C5	0.0347 (12)	0.0401 (13)	0.0557 (14)	−0.0018 (10)	0.0076 (10)	0.0007 (10)
C6	0.0358 (12)	0.0447 (14)	0.0507 (14)	0.0008 (10)	0.0016 (10)	0.0023 (10)
C7	0.0405 (13)	0.0360 (13)	0.0637 (16)	−0.0013 (11)	0.0095 (12)	−0.0001 (11)
C8	0.0408 (13)	0.0457 (14)	0.0407 (12)	0.0064 (10)	0.0053 (10)	−0.0035 (10)
C9	0.0399 (13)	0.0509 (15)	0.0445 (13)	0.0042 (11)	0.0013 (10)	−0.0017 (11)
C10	0.0501 (15)	0.0627 (18)	0.0640 (17)	0.0177 (14)	0.0043 (13)	0.0021 (13)
C11	0.0689 (19)	0.0462 (16)	0.0692 (18)	0.0145 (14)	0.0113 (14)	−0.0005 (13)
C12	0.0631 (16)	0.0470 (15)	0.0495 (14)	−0.0038 (13)	0.0081 (12)	−0.0047 (11)
C13	0.0434 (14)	0.0513 (16)	0.0494 (14)	0.0011 (11)	0.0013 (11)	−0.0036 (11)

N1—C8	1.369 (3)	C3—H3A	0.9300
N1—C6	1.402 (3)	C4—C5	1.399 (3)
N1—H1A	0.8600	C4—H4A	0.9300
O1—C7	1.309 (3)	C5—C6	1.402 (3)
O1—H1C	0.8200	C5—C7	1.472 (3)
C1—C2	1.374 (3)	C8—C13	1.407 (3)
C1—C6	1.392 (3)	C8—C9	1.407 (3)
C1—H1B	0.9300	C9—C10	1.391 (3)
O2—C7	1.233 (3)	C10—C11	1.368 (4)
N2—O3	1.218 (3)	C10—H10A	0.9300
N2—O4	1.222 (3)	C11—C12	1.385 (4)
N2—C9	1.451 (3)	C11—H11A	0.9300
C2—C3	1.382 (4)	C12—C13	1.366 (3)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.363 (3)	C13—H13A	0.9300
C8—N1—C6	127.5 (2)	C1—C6—C5	118.6 (2)
C8—N1—H1A	116.2	N1—C6—C5	120.9 (2)
C6—N1—H1A	116.2	O2—C7—O1	121.9 (2)
C7—O1—H1C	109.5	O2—C7—C5	123.5 (2)
C2—C1—C6	121.2 (2)	O1—C7—C5	114.6 (2)
C2—C1—H1B	119.4	N1—C8—C13	121.4 (2)
C6—C1—H1B	119.4	N1—C8—C9	122.9 (2)
O3—N2—O4	120.9 (2)	C13—C8—C9	115.7 (2)
O3—N2—C9	120.3 (2)	C10—C9—C8	121.7 (2)
O4—N2—C9	118.8 (2)	C10—C9—N2	116.6 (2)
C1—C2—C3	120.5 (2)	C8—C9—N2	121.6 (2)
C1—C2—H2A	119.8	C11—C10—C9	120.6 (2)
C3—C2—H2A	119.8	C11—C10—H10A	119.7
C4—C3—C2	119.0 (2)	C9—C10—H10A	119.7
C4—C3—H3A	120.5	C10—C11—C12	118.8 (2)
C2—C3—H3A	120.5	C10—C11—H11A	120.6
C3—C4—C5	122.1 (2)	C12—C11—H11A	120.6
C3—C4—H4A	119.0	C13—C12—C11	121.0 (2)
C5—C4—H4A	119.0	C13—C12—H12A	119.5
C4—C5—C6	118.6 (2)	C11—C12—H12A	119.5
C4—C5—C7	118.7 (2)	C12—C13—C8	122.1 (2)
C6—C5—C7	122.7 (2)	C12—C13—H13A	119.0
C1—C6—N1	120.3 (2)	C8—C13—H13A	119.0
C6—C1—C2—C3	0.0 (4)	C6—N1—C8—C13	22.6 (4)
C1—C2—C3—C4	−0.6 (4)	C6—N1—C8—C9	−160.5 (2)
C2—C3—C4—C5	1.1 (4)	N1—C8—C9—C10	−176.0 (2)
C3—C4—C5—C6	−1.1 (4)	C13—C8—C9—C10	1.1 (3)
C3—C4—C5—C7	−179.1 (2)	N1—C8—C9—N2	4.1 (4)
C2—C1—C6—N1	175.9 (2)	C13—C8—C9—N2	−178.8 (2)
C2—C1—C6—C5	0.0 (4)	O3—N2—C9—C10	165.3 (2)
C8—N1—C6—C1	34.3 (4)	O4—N2—C9—C10	−14.0 (4)
C8—N1—C6—C5	−149.9 (2)	O3—N2—C9—C8	−14.8 (4)
C4—C5—C6—C1	0.5 (3)	O4—N2—C9—C8	165.9 (3)
C7—C5—C6—C1	178.5 (2)	C8—C9—C10—C11	−0.4 (4)
C4—C5—C6—N1	−175.3 (2)	N2—C9—C10—C11	179.5 (2)
C7—C5—C6—N1	2.6 (4)	C9—C10—C11—C12	−1.2 (4)
C4—C5—C7—O2	172.6 (2)	C10—C11—C12—C13	2.1 (4)
C6—C5—C7—O2	−5.4 (4)	C11—C12—C13—C8	−1.4 (4)
C4—C5—C7—O1	−7.2 (3)	N1—C8—C13—C12	176.9 (2)
C6—C5—C7—O1	174.8 (2)	C9—C8—C13—C12	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.86	2.02	2.636 (3)	128.
O1—H1C···O2i	0.82	1.82	2.636 (2)	176.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.86	2.02	2.636 (3)	128
O1—H1C⋯O2i	0.82	1.82	2.636 (2)	176

Symmetry code: (i) .