3-Amino-benzoic acid-4-nitro-benzoic acid (1/1).

In the title 1:1 adduct, C(7)H(5)NO(4)·C(7)H(7)NO(2), the nitro group of the 4-nitro benzoic acid is twisted from the attached ring by 4.40 (8)°. In the crystal, the mol-ecules are linked into ribbon-like structures along [150] and [10] via O-H⋯O, N-H⋯O, N-H⋯N and C-H⋯O inter-molecular hydrogen bonds.

Related literature

For the applications of 3-amino­benzoic acid, see; Windholz (1976 ▶). For related structures, see: Bowers et al. (2005 ▶); Tonogaki et al. (1993 ▶); Voogd et al. (1980 ▶).

Experimental

Crystal data

C7H5NO4·C7H7NO2

M = 304.26

Monoclinic,

a = 25.3707 (8) Å

b = 4.9875 (2) Å

c = 21.7276 (7) Å

β = 109.230 (2)°

V = 2595.93 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 100.0 (1) K

0.24 × 0.09 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.971, T max = 0.993

15472 measured reflections

3759 independent reflections

2197 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.179

S = 1.01

3759 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037112/ci2714sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037112/ci2714Isup2.hkl

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

C7H5NO4·C7H7NO2	F000 = 1264
Mr = 304.26	Dx = 1.557 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2404 reflections
a = 25.3707 (8) Å	θ = 3.0–29.9º
b = 4.9875 (2) Å	µ = 0.12 mm−1
c = 21.7276 (7) Å	T = 100.0 (1) K
β = 109.230 (2)º	Plate, yellow
V = 2595.93 (16) Å3	0.24 × 0.09 × 0.06 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	3759 independent reflections
Radiation source: fine-focus sealed tube	2197 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.068
T = 100.0(1) K	θmax = 30.0º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −34→35
Tmin = 0.971, Tmax = 0.993	k = −7→7
15472 measured reflections	l = −29→30

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)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.179	w = 1/[σ2(Fo2) + (0.087P)2 + 1.6119P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
3759 reflections	Δρmax = 0.50 e Å−3
215 parameters	Δρmin = −0.36 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
O1	0.82025 (7)	0.6966 (4)	0.14306 (8)	0.0238 (4)
O2	0.81699 (7)	0.7604 (3)	0.04310 (8)	0.0236 (4)
O3	1.01559 (7)	−0.2306 (3)	0.07932 (8)	0.0175 (4)
O4	1.01017 (7)	−0.3174 (3)	0.17847 (8)	0.0183 (4)
O5	0.57710 (6)	0.7825 (3)	0.18023 (8)	0.0180 (4)
O6	0.58739 (7)	0.8769 (4)	0.08408 (8)	0.0194 (4)
N1	0.83479 (8)	0.6430 (4)	0.09588 (9)	0.0178 (4)
N2	0.73488 (9)	0.2432 (5)	0.06366 (11)	0.0217 (5)
C1	0.93325 (9)	0.0854 (5)	0.16778 (11)	0.0166 (5)
H1A	0.9461	−0.0152	0.2070	0.020*
C2	0.89370 (9)	0.2853 (5)	0.16067 (11)	0.0167 (5)
H2A	0.8792	0.3241	0.1948	0.020*
C3	0.87598 (9)	0.4267 (5)	0.10277 (11)	0.0158 (5)
C4	0.89605 (9)	0.3786 (5)	0.05146 (11)	0.0160 (5)
H4A	0.8831	0.4800	0.0123	0.019*
C5	0.93576 (9)	0.1775 (5)	0.05923 (11)	0.0164 (5)
H5A	0.9503	0.1395	0.0251	0.020*
C6	0.95413 (8)	0.0322 (5)	0.11703 (10)	0.0136 (5)
C7	0.99642 (9)	−0.1847 (4)	0.12311 (11)	0.0145 (5)
C8	0.66801 (9)	0.4869 (5)	0.10050 (11)	0.0172 (5)
H8A	0.6584	0.5966	0.0627	0.021*
C9	0.70819 (9)	0.2837 (5)	0.10949 (11)	0.0179 (5)
C10	0.72180 (10)	0.1297 (5)	0.16603 (12)	0.0199 (5)
H10A	0.7492	−0.0069	0.1728	0.024*
C11	0.69646 (9)	0.1707 (5)	0.21230 (12)	0.0203 (5)
H11A	0.7066	0.0630	0.2505	0.024*
C12	0.65613 (9)	0.3688 (5)	0.20347 (11)	0.0180 (5)
H12A	0.6383	0.3962	0.2351	0.022*
C13	0.64223 (9)	0.5267 (5)	0.14746 (11)	0.0152 (5)
C14	0.59973 (9)	0.7398 (4)	0.13881 (11)	0.0143 (5)
H1O4	1.0354 (14)	−0.442 (8)	0.1783 (15)	0.056 (11)*
H1O6	0.5600 (15)	0.998 (8)	0.0809 (16)	0.063 (11)*
H1N1	0.7575 (14)	0.064 (8)	0.0643 (16)	0.063 (11)*
H2N2	0.7158 (12)	0.302 (6)	0.0233 (14)	0.029 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0264 (9)	0.0247 (10)	0.0238 (10)	0.0060 (7)	0.0131 (8)	−0.0027 (7)
O2	0.0266 (9)	0.0214 (10)	0.0227 (9)	0.0058 (7)	0.0079 (7)	0.0042 (7)
O3	0.0198 (8)	0.0161 (9)	0.0190 (8)	0.0049 (7)	0.0095 (7)	0.0019 (7)
O4	0.0226 (9)	0.0164 (9)	0.0182 (9)	0.0086 (7)	0.0098 (7)	0.0039 (7)
O5	0.0213 (8)	0.0155 (9)	0.0190 (9)	0.0037 (7)	0.0090 (7)	0.0012 (7)
O6	0.0222 (9)	0.0206 (9)	0.0185 (9)	0.0069 (7)	0.0108 (7)	0.0035 (7)
N1	0.0180 (9)	0.0171 (10)	0.0187 (10)	0.0008 (8)	0.0067 (8)	−0.0014 (8)
N2	0.0229 (11)	0.0244 (12)	0.0197 (11)	0.0051 (9)	0.0096 (9)	0.0015 (9)
C1	0.0168 (11)	0.0159 (12)	0.0173 (12)	0.0005 (9)	0.0060 (9)	0.0008 (9)
C2	0.0180 (11)	0.0171 (12)	0.0173 (12)	−0.0008 (9)	0.0091 (9)	−0.0019 (9)
C3	0.0123 (10)	0.0125 (12)	0.0227 (12)	0.0023 (8)	0.0057 (9)	−0.0028 (9)
C4	0.0180 (11)	0.0138 (11)	0.0173 (12)	0.0020 (9)	0.0073 (9)	0.0034 (9)
C5	0.0181 (11)	0.0164 (12)	0.0168 (12)	0.0000 (9)	0.0087 (9)	0.0002 (9)
C6	0.0121 (10)	0.0125 (11)	0.0164 (11)	−0.0018 (8)	0.0051 (8)	−0.0007 (9)
C7	0.0139 (10)	0.0132 (12)	0.0169 (12)	−0.0018 (9)	0.0058 (9)	−0.0010 (9)
C8	0.0174 (11)	0.0155 (12)	0.0195 (12)	−0.0017 (9)	0.0073 (9)	−0.0011 (9)
C9	0.0151 (11)	0.0173 (12)	0.0222 (12)	−0.0025 (9)	0.0075 (9)	−0.0058 (9)
C10	0.0172 (11)	0.0151 (12)	0.0251 (13)	0.0029 (9)	0.0040 (10)	−0.0019 (10)
C11	0.0193 (12)	0.0179 (13)	0.0224 (13)	0.0012 (9)	0.0052 (10)	0.0006 (9)
C12	0.0184 (11)	0.0163 (12)	0.0197 (12)	0.0025 (9)	0.0069 (9)	0.0000 (9)
C13	0.0126 (10)	0.0138 (11)	0.0201 (12)	0.0010 (9)	0.0066 (9)	−0.0014 (9)
C14	0.0140 (10)	0.0137 (11)	0.0155 (11)	0.0000 (9)	0.0053 (8)	−0.0014 (9)

O1—N1	1.228 (2)	C3—C4	1.391 (3)
O2—N1	1.233 (2)	C4—C5	1.392 (3)
O3—C7	1.225 (3)	C4—H4A	0.95
O4—C7	1.315 (3)	C5—C6	1.391 (3)
O4—H1O4	0.89 (4)	C5—H5A	0.95
O5—C14	1.235 (3)	C6—C7	1.498 (3)
O6—C14	1.317 (3)	C8—C13	1.396 (3)
O6—H1O6	0.91 (4)	C8—C9	1.405 (3)
N1—C3	1.475 (3)	C8—H8A	0.95
N2—C9	1.391 (3)	C9—C10	1.392 (3)
N2—H1N1	1.06 (4)	C10—C11	1.375 (3)
N2—H2N2	0.90 (3)	C10—H10A	0.95
C1—C2	1.387 (3)	C11—C12	1.390 (3)
C1—C6	1.397 (3)	C11—H11A	0.95
C1—H1A	0.95	C12—C13	1.394 (3)
C2—C3	1.382 (3)	C12—H12A	0.95
C2—H2A	0.95	C13—C14	1.481 (3)
C7—O4—H1O4	109 (2)	C1—C6—C7	120.9 (2)
C14—O6—H1O6	111 (2)	O3—C7—O4	124.3 (2)
O1—N1—O2	123.7 (2)	O3—C7—C6	121.5 (2)
O1—N1—C3	118.17 (19)	O4—C7—C6	114.23 (19)
O2—N1—C3	118.17 (18)	C13—C8—C9	119.6 (2)
C9—N2—H1N1	120.1 (18)	C13—C8—H8A	120.2
C9—N2—H2N2	114.7 (18)	C9—C8—H8A	120.2
H1N1—N2—H2N2	114 (3)	N2—C9—C10	120.9 (2)
C2—C1—C6	119.8 (2)	N2—C9—C8	120.5 (2)
C2—C1—H1A	120.1	C10—C9—C8	118.6 (2)
C6—C1—H1A	120.1	C11—C10—C9	121.5 (2)
C3—C2—C1	118.3 (2)	C11—C10—H10A	119.2
C3—C2—H2A	120.8	C9—C10—H10A	119.2
C1—C2—H2A	120.8	C10—C11—C12	120.3 (2)
C2—C3—C4	123.1 (2)	C10—C11—H11A	119.8
C2—C3—N1	118.23 (19)	C12—C11—H11A	119.8
C4—C3—N1	118.6 (2)	C11—C12—C13	119.0 (2)
C3—C4—C5	117.9 (2)	C11—C12—H12A	120.5
C3—C4—H4A	121.0	C13—C12—H12A	120.5
C5—C4—H4A	121.0	C12—C13—C8	120.9 (2)
C6—C5—C4	119.9 (2)	C12—C13—C14	118.7 (2)
C6—C5—H5A	120.0	C8—C13—C14	120.4 (2)
C4—C5—H5A	120.0	O5—C14—O6	122.6 (2)
C5—C6—C1	120.8 (2)	O5—C14—C13	121.7 (2)
C5—C6—C7	118.24 (19)	O6—C14—C13	115.72 (19)
C6—C1—C2—C3	0.1 (3)	C5—C6—C7—O4	−178.0 (2)
C1—C2—C3—C4	−0.3 (3)	C1—C6—C7—O4	1.3 (3)
C1—C2—C3—N1	−178.7 (2)	C13—C8—C9—N2	−179.2 (2)
O1—N1—C3—C2	3.6 (3)	C13—C8—C9—C10	−1.0 (3)
O2—N1—C3—C2	−176.6 (2)	N2—C9—C10—C11	178.8 (2)
O1—N1—C3—C4	−175.0 (2)	C8—C9—C10—C11	0.7 (3)
O2—N1—C3—C4	4.9 (3)	C9—C10—C11—C12	0.1 (4)
C2—C3—C4—C5	0.2 (3)	C10—C11—C12—C13	−0.7 (3)
N1—C3—C4—C5	178.7 (2)	C11—C12—C13—C8	0.3 (3)
C3—C4—C5—C6	−0.1 (3)	C11—C12—C13—C14	−179.2 (2)
C4—C5—C6—C1	0.0 (3)	C9—C8—C13—C12	0.5 (3)
C4—C5—C6—C7	179.3 (2)	C9—C8—C13—C14	−179.9 (2)
C2—C1—C6—C5	0.0 (3)	C12—C13—C14—O5	1.0 (3)
C2—C1—C6—C7	−179.3 (2)	C8—C13—C14—O5	−178.6 (2)
C5—C6—C7—O3	1.7 (3)	C12—C13—C14—O6	−178.2 (2)
C1—C6—C7—O3	−179.0 (2)	C8—C13—C14—O6	2.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O5i	0.89 (4)	1.73 (4)	2.612 (2)	171 (3)
O6—H1O6···O3ii	0.91 (4)	1.75 (4)	2.652 (2)	171 (4)
N2—H1N1···O2iii	1.06 (4)	2.29 (4)	3.309 (3)	161 (3)
N2—H2N2···O2iv	0.90 (3)	2.60 (3)	3.351 (3)	142 (2)
C2—H2A···O5v	0.95	2.58	3.288 (3)	131
C4—H4A···O6iv	0.95	2.55	3.339 (3)	141
C10—H10A···O1iii	0.95	2.57	3.460 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O5i	0.89 (4)	1.73 (4)	2.612 (2)	171 (3)
O6—H1O6⋯O3ii	0.91 (4)	1.75 (4)	2.652 (2)	171 (4)
N2—H1N1⋯O2iii	1.06 (4)	2.29 (4)	3.309 (3)	161 (3)
N2—H2N2⋯O2iv	0.90 (3)	2.60 (3)	3.351 (3)	142 (2)
C2—H2A⋯O5v	0.95	2.58	3.288 (3)	131
C4—H4A⋯O6iv	0.95	2.55	3.339 (3)	141
C10—H10A⋯O1iii	0.95	2.57	3.460 (3)	156

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