2-Meth-oxy-carbonyl-6-nitro-benzoic acid.

In the title compound, C(9)H(7)NO(6), the dihedral angles between the benzene ring and its three substituents are 29.99 (8)° for the nitro, 67.09 (8)° for the carb-oxy and 32.48 (10)° for the meth-oxy-carbonyl group. In the crystal, one classical O-H⋯O and two nonclassical C-H⋯O contacts link adjacent mol-ecules, forming a three-dimensional structure.

Related literature

For the bioactivity of the title compound, see: Xu & He (2010 ▶). For related structures, see: Glidewell et al. (2003 ▶); Wang et al. (2006 ▶).

Experimental

Crystal data

C9H7NO6

M = 225.16

Orthorhombic,

a = 7.647 (3) Å

b = 8.145 (3) Å

c = 15.583 (6) Å

V = 970.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.27 × 0.22 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

6820 measured reflections

1010 independent reflections

982 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.077

S = 1.05

1010 reflections

151 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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) global, I. DOI: 10.1107/S1600536812030462/sj5245sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030462/sj5245Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030462/sj5245Isup3.cml

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

C9H7NO6	Dx = 1.541 Mg m−3
Mr = 225.16	Melting point = 429–431 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6294 reflections
a = 7.647 (3) Å	θ = 2.6–27.1°
b = 8.145 (3) Å	µ = 0.13 mm−1
c = 15.583 (6) Å	T = 296 K
V = 970.6 (7) Å3	Block, colourless
Z = 4	0.27 × 0.22 × 0.16 mm
F(000) = 464

Bruker SMART CCD area-detector diffractometer	982 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 25.0°, θmin = 3.0°
φ and ω scans	h = −9→9
6820 measured reflections	k = −8→9
1010 independent reflections	l = −18→18

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)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0524P)2 + 0.1444P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
1010 reflections	Δρmax = 0.13 e Å−3
151 parameters	Δρmin = −0.13 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.058 (7)

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
O6	1.15166 (19)	0.64183 (18)	0.90968 (8)	0.0467 (4)
O5	1.0302 (2)	0.41107 (19)	0.95864 (9)	0.0504 (4)
O4	0.6725 (2)	0.22147 (17)	0.89827 (8)	0.0481 (4)
O3	0.6525 (2)	0.4616 (2)	0.96756 (9)	0.0503 (4)
C5	0.7676 (2)	0.4546 (2)	0.82508 (10)	0.0319 (4)
O2	0.4446 (3)	0.3360 (3)	0.67750 (11)	0.0790 (6)
C2	0.9167 (3)	0.5774 (3)	0.67363 (12)	0.0481 (5)
H2A	0.9677	0.6167	0.6235	0.058*
O1	0.4073 (2)	0.4102 (3)	0.80807 (11)	0.0694 (5)
C6	0.6778 (2)	0.4551 (2)	0.74720 (11)	0.0359 (4)
N1	0.4967 (3)	0.3961 (2)	0.74398 (12)	0.0466 (4)
C8	1.0429 (2)	0.5175 (2)	0.90536 (11)	0.0343 (4)
C7	0.6900 (2)	0.3825 (2)	0.90552 (11)	0.0353 (4)
C4	0.9356 (2)	0.5210 (2)	0.82510 (10)	0.0342 (4)
C9	1.2706 (3)	0.6459 (3)	0.98203 (13)	0.0532 (6)
H9A	1.3540	0.7327	0.9741	0.064*
H9B	1.3310	0.5429	0.9861	0.064*
H9C	1.2057	0.6649	1.0338	0.064*
C3	1.0080 (3)	0.5825 (3)	0.74992 (13)	0.0430 (5)
H3A	1.1197	0.6277	0.7510	0.052*
C1	0.7503 (3)	0.5143 (2)	0.67198 (11)	0.0436 (5)
H1A	0.6872	0.5112	0.6210	0.052*
H1	0.630 (4)	0.178 (3)	0.9437 (12)	0.078 (9)*

	U11	U22	U33	U12	U13	U23
O6	0.0477 (8)	0.0497 (8)	0.0428 (7)	−0.0100 (7)	−0.0081 (6)	0.0050 (6)
O5	0.0555 (8)	0.0542 (8)	0.0414 (7)	−0.0066 (7)	−0.0148 (7)	0.0176 (7)
O4	0.0640 (9)	0.0431 (7)	0.0372 (7)	−0.0043 (7)	0.0154 (7)	0.0068 (6)
O3	0.0594 (9)	0.0603 (9)	0.0311 (7)	0.0006 (8)	0.0088 (6)	−0.0060 (6)
C5	0.0369 (8)	0.0321 (8)	0.0267 (8)	0.0043 (7)	0.0019 (7)	0.0008 (7)
O2	0.0743 (11)	0.1103 (15)	0.0524 (9)	−0.0313 (12)	−0.0165 (9)	−0.0122 (10)
C2	0.0598 (12)	0.0531 (12)	0.0314 (9)	−0.0055 (10)	0.0045 (9)	0.0121 (8)
O1	0.0423 (8)	0.1073 (15)	0.0587 (9)	−0.0063 (10)	0.0043 (8)	−0.0097 (10)
C6	0.0399 (9)	0.0363 (9)	0.0315 (8)	0.0017 (8)	−0.0011 (8)	0.0015 (7)
N1	0.0461 (8)	0.0542 (10)	0.0396 (8)	−0.0007 (8)	−0.0091 (7)	0.0012 (8)
C8	0.0350 (8)	0.0374 (9)	0.0304 (8)	0.0036 (8)	0.0021 (7)	0.0026 (8)
C7	0.0341 (8)	0.0443 (10)	0.0275 (8)	0.0014 (8)	0.0016 (8)	0.0021 (8)
C4	0.0397 (9)	0.0339 (8)	0.0290 (8)	0.0022 (8)	−0.0002 (7)	0.0042 (7)
C9	0.0470 (11)	0.0652 (13)	0.0473 (10)	−0.0074 (11)	−0.0104 (9)	−0.0036 (10)
C3	0.0447 (9)	0.0479 (11)	0.0364 (8)	−0.0054 (9)	0.0029 (7)	0.0111 (8)
C1	0.0568 (11)	0.0468 (10)	0.0271 (8)	0.0025 (9)	−0.0064 (8)	0.0055 (8)

O6—C8	1.312 (2)	C2—H2A	0.9300
O6—C9	1.449 (2)	O1—N1	1.216 (3)
O5—C8	1.204 (2)	C6—C1	1.383 (3)
O4—C7	1.323 (3)	C6—N1	1.467 (3)
O4—H1	0.856 (10)	C8—C4	1.496 (2)
O3—C7	1.197 (2)	C4—C3	1.389 (3)
C5—C4	1.394 (3)	C9—H9A	0.9600
C5—C6	1.394 (2)	C9—H9B	0.9600
C5—C7	1.506 (2)	C9—H9C	0.9600
O2—N1	1.213 (2)	C3—H3A	0.9300
C2—C1	1.373 (3)	C1—H1A	0.9300
C2—C3	1.380 (3)
C8—O6—C9	117.11 (15)	O3—C7—C5	123.81 (18)
C7—O4—H1	112 (2)	O4—C7—C5	110.80 (15)
C4—C5—C6	116.91 (16)	C3—C4—C5	120.48 (17)
C4—C5—C7	120.96 (15)	C3—C4—C8	119.57 (17)
C6—C5—C7	122.11 (16)	C5—C4—C8	119.86 (15)
C1—C2—C3	119.78 (18)	O6—C9—H9A	109.5
C1—C2—H2A	120.1	O6—C9—H9B	109.5
C3—C2—H2A	120.1	H9A—C9—H9B	109.5
C1—C6—C5	122.78 (18)	O6—C9—H9C	109.5
C1—C6—N1	117.60 (17)	H9A—C9—H9C	109.5
C5—C6—N1	119.58 (16)	H9B—C9—H9C	109.5
O2—N1—O1	123.7 (2)	C2—C3—C4	120.93 (19)
O2—N1—C6	118.15 (19)	C2—C3—H3A	119.5
O1—N1—C6	118.16 (17)	C4—C3—H3A	119.5
O5—C8—O6	124.84 (17)	C2—C1—C6	119.08 (18)
O5—C8—C4	123.11 (17)	C2—C1—H1A	120.5
O6—C8—C4	112.05 (14)	C6—C1—H1A	120.5
O3—C7—O4	125.37 (18)
C4—C5—C6—C1	1.6 (3)	C6—C5—C4—C3	−0.7 (3)
C7—C5—C6—C1	−177.04 (16)	C7—C5—C4—C3	177.95 (18)
C4—C5—C6—N1	−176.33 (16)	C6—C5—C4—C8	−177.14 (16)
C7—C5—C6—N1	5.0 (3)	C7—C5—C4—C8	1.5 (2)
C1—C6—N1—O2	30.9 (3)	O5—C8—C4—C3	−145.9 (2)
C5—C6—N1—O2	−151.0 (2)	O6—C8—C4—C3	33.4 (2)
C1—C6—N1—O1	−149.0 (2)	O5—C8—C4—C5	30.5 (3)
C5—C6—N1—O1	29.0 (3)	O6—C8—C4—C5	−150.10 (16)
C9—O6—C8—O5	3.2 (3)	C1—C2—C3—C4	1.5 (3)
C9—O6—C8—C4	−176.16 (16)	C5—C4—C3—C2	−0.8 (3)
C4—C5—C7—O3	67.3 (2)	C8—C4—C3—C2	175.65 (18)
C6—C5—C7—O3	−114.1 (2)	C3—C2—C1—C6	−0.6 (3)
C4—C5—C7—O4	−111.59 (18)	C5—C6—C1—C2	−0.9 (3)
C6—C5—C7—O4	67.0 (2)	N1—C6—C1—C2	177.02 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1···O5i	0.86 (1)	1.85 (1)	2.706 (2)	178 (3)
C9—H9C···O2ii	0.96	2.52	3.465 (3)	170
C9—H9B···O3iii	0.96	2.56	3.291 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1⋯O5i	0.86 (1)	1.85 (1)	2.706 (2)	178 (3)
C9—H9C⋯O2ii	0.96	2.52	3.465 (3)	170
C9—H9B⋯O3iii	0.96	2.56	3.291 (3)	133

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