2-Hydr-oxy-3-nitro-benzamide.

The asymmetric unit of title compound, C(7)H(6)N(2)O(4), contains two mol-ecules, one of which has a disordered nitro group with an occupancy ratio of 0.517 (9):0.483 (9) for the O atoms. Both mol-ecules contain an intra-molecular O-H⋯O hydrogen bond. In the crystal, both mol-ecules form inversion dimers linked by pairs of N-H⋯O hydrogen bonds, resulting in R(2) (2)(8) ring motifs. The dimers are connected by further N-H⋯O links and weak C-H⋯O inter-actions, resulting in a layered motif.

Related literature

For related structures, see: Liu & Zhu (2007 ▶); Pertlik (1990 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H6N2O4

M = 182.14

Triclinic,

a = 3.8390 (2) Å

b = 13.0347 (8) Å

c = 16.0409 (9) Å

α = 98.207 (3)°

β = 95.658 (2)°

γ = 98.365 (3)°

V = 780.16 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.25 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.966, T max = 0.979

15183 measured reflections

3658 independent reflections

1932 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.139

S = 1.00

3658 reflections

287 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022843/hb5009sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022843/hb5009Isup2.hkl

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

C7H6N2O4	Z = 4
Mr = 182.14	F(000) = 376
Triclinic, P1	Dx = 1.551 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8390 (2) Å	Cell parameters from 3658 reflections
b = 13.0347 (8) Å	θ = 1.3–27.9°
c = 16.0409 (9) Å	µ = 0.13 mm−1
α = 98.207 (3)°	T = 296 K
β = 95.658 (2)°	Prism, brown
γ = 98.365 (3)°	0.25 × 0.22 × 0.18 mm
V = 780.16 (8) Å3

Bruker Kappa APEXII CCD diffractometer	3658 independent reflections
Radiation source: fine-focus sealed tube	1932 reflections with I > 2σ(I)
graphite	Rint = 0.039
Detector resolution: 7.40 pixels mm-1	θmax = 27.9°, θmin = 1.3°
ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −17→16
Tmin = 0.966, Tmax = 0.979	l = −20→20
15183 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.1478P] where P = (Fo2 + 2Fc2)/3
3658 reflections	(Δ/σ)max < 0.001
287 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
O5	1.3003 (4)	0.14269 (11)	0.28007 (10)	0.0574 (6)
O6A	1.0846 (17)	0.2123 (3)	0.1437 (3)	0.0622 (16)	0.517 (9)
O7A	0.9012 (16)	0.0976 (4)	0.0315 (3)	0.0726 (16)	0.517 (9)
O8	1.4309 (4)	0.06126 (12)	0.40897 (9)	0.0602 (6)
N3	0.9800 (5)	0.12260 (17)	0.11120 (12)	0.0517 (8)
N4	1.1499 (6)	−0.09612 (17)	0.42380 (13)	0.0584 (7)
C8	1.0438 (5)	−0.03373 (16)	0.28965 (12)	0.0398 (6)
C9	1.1008 (5)	0.05167 (16)	0.24507 (12)	0.0390 (6)
C10	0.9365 (5)	0.03748 (17)	0.16144 (13)	0.0416 (7)
C11	0.7300 (6)	−0.05660 (19)	0.12321 (14)	0.0488 (8)
C12	0.6838 (6)	−0.1393 (2)	0.16654 (14)	0.0522 (8)
C13	0.8391 (6)	−0.12754 (18)	0.24892 (14)	0.0476 (8)
C14	1.2174 (5)	−0.02094 (17)	0.37827 (13)	0.0442 (7)
O7B	1.2731 (16)	0.1761 (5)	0.1186 (3)	0.0686 (17)	0.483 (9)
O6B	0.7212 (15)	0.1376 (4)	0.0676 (4)	0.0765 (19)	0.483 (9)
O1	1.1680 (4)	0.64772 (12)	0.23085 (10)	0.0576 (6)
O2	1.6092 (5)	0.69953 (13)	0.37229 (11)	0.0717 (7)
O3	1.3820 (6)	0.64564 (16)	0.47695 (12)	0.0965 (9)
O4	0.7934 (4)	0.56454 (13)	0.09498 (10)	0.0650 (6)
N1	1.4064 (5)	0.63841 (15)	0.40149 (12)	0.0521 (7)
N2	0.5075 (6)	0.40043 (18)	0.07421 (14)	0.0632 (8)
C1	0.8539 (5)	0.47141 (16)	0.21067 (13)	0.0412 (7)
C2	1.0752 (5)	0.55872 (16)	0.26058 (13)	0.0409 (7)
C3	1.1871 (5)	0.54999 (16)	0.34496 (13)	0.0418 (7)
C4	1.0917 (6)	0.45937 (19)	0.37779 (15)	0.0492 (8)
C5	0.8859 (6)	0.37445 (19)	0.32808 (15)	0.0543 (8)
C6	0.7662 (6)	0.38048 (18)	0.24564 (14)	0.0482 (8)
C7	0.7143 (6)	0.48026 (19)	0.12263 (14)	0.0475 (8)
H4B	0.984 (7)	−0.1544 (19)	0.4054 (15)	0.0701*
H5O	1.38739	0.13813	0.32790	0.0689*
H12	0.533 (7)	−0.208 (2)	0.1414 (15)	0.075 (7)*
H13	0.808 (6)	−0.1821 (18)	0.2792 (14)	0.0571*
H11	0.632 (6)	−0.0653 (17)	0.0674 (15)	0.0586*
H4A	1.260 (7)	−0.0911 (19)	0.4746 (17)	0.0701*
H1O	1.07785	0.64178	0.18153	0.0692*
H2A	0.444 (7)	0.347 (2)	0.0911 (17)	0.0758*
H2B	0.420 (6)	0.4100 (19)	0.0199 (17)	0.0758*
H4	1.161 (6)	0.4557 (17)	0.4324 (15)	0.0589*
H5	0.820 (6)	0.3154 (19)	0.3482 (15)	0.0651*
H6	0.614 (6)	0.3254 (18)	0.2137 (14)	0.0578*

	U11	U22	U33	U12	U13	U23
O5	0.0718 (10)	0.0450 (10)	0.0451 (9)	−0.0112 (8)	−0.0179 (8)	0.0107 (7)
O6A	0.079 (3)	0.052 (3)	0.053 (2)	0.000 (2)	−0.002 (2)	0.0178 (19)
O7A	0.075 (3)	0.097 (3)	0.038 (2)	−0.010 (2)	−0.011 (2)	0.021 (2)
O8	0.0729 (10)	0.0528 (10)	0.0431 (9)	−0.0137 (8)	−0.0177 (8)	0.0098 (8)
N3	0.0482 (12)	0.0617 (15)	0.0429 (12)	0.0011 (10)	−0.0054 (9)	0.0157 (11)
N4	0.0716 (14)	0.0557 (13)	0.0403 (11)	−0.0074 (10)	−0.0156 (10)	0.0154 (10)
C8	0.0405 (10)	0.0413 (12)	0.0345 (11)	0.0025 (9)	−0.0022 (9)	0.0042 (10)
C9	0.0362 (10)	0.0402 (12)	0.0362 (11)	0.0001 (9)	−0.0040 (8)	0.0032 (9)
C10	0.0379 (10)	0.0486 (14)	0.0373 (12)	0.0035 (9)	−0.0005 (9)	0.0108 (10)
C11	0.0467 (12)	0.0599 (16)	0.0330 (12)	−0.0004 (11)	−0.0075 (10)	0.0023 (11)
C12	0.0548 (13)	0.0498 (15)	0.0428 (14)	−0.0073 (11)	−0.0062 (10)	0.0011 (12)
C13	0.0542 (13)	0.0437 (14)	0.0406 (13)	−0.0031 (10)	−0.0013 (10)	0.0086 (10)
C14	0.0482 (12)	0.0459 (13)	0.0353 (12)	0.0034 (10)	−0.0036 (9)	0.0062 (10)
O7B	0.060 (3)	0.071 (3)	0.070 (3)	−0.016 (2)	−0.008 (2)	0.033 (2)
O6B	0.064 (3)	0.092 (3)	0.074 (4)	0.010 (2)	−0.020 (3)	0.037 (3)
O1	0.0725 (11)	0.0494 (10)	0.0490 (10)	−0.0047 (8)	−0.0044 (8)	0.0242 (8)
O2	0.0808 (12)	0.0613 (12)	0.0630 (11)	−0.0209 (9)	0.0007 (9)	0.0152 (9)
O3	0.1297 (18)	0.0999 (16)	0.0415 (11)	−0.0298 (13)	−0.0012 (11)	0.0073 (10)
O4	0.0848 (11)	0.0577 (11)	0.0489 (10)	−0.0052 (9)	−0.0095 (8)	0.0257 (8)
N1	0.0565 (11)	0.0520 (12)	0.0454 (12)	0.0023 (9)	−0.0024 (9)	0.0127 (10)
N2	0.0773 (14)	0.0598 (15)	0.0466 (12)	−0.0077 (12)	−0.0122 (10)	0.0217 (11)
C1	0.0417 (11)	0.0458 (13)	0.0385 (12)	0.0082 (9)	0.0049 (9)	0.0141 (10)
C2	0.0428 (11)	0.0416 (12)	0.0412 (12)	0.0061 (9)	0.0066 (9)	0.0160 (10)
C3	0.0416 (11)	0.0439 (13)	0.0406 (12)	0.0054 (9)	0.0041 (9)	0.0117 (10)
C4	0.0521 (12)	0.0568 (15)	0.0406 (13)	0.0065 (11)	0.0005 (10)	0.0206 (12)
C5	0.0604 (14)	0.0493 (15)	0.0530 (15)	−0.0013 (12)	−0.0022 (11)	0.0242 (12)
C6	0.0495 (13)	0.0465 (14)	0.0468 (14)	0.0007 (10)	−0.0010 (10)	0.0137 (11)
C7	0.0494 (12)	0.0520 (14)	0.0424 (13)	0.0063 (11)	0.0028 (10)	0.0158 (11)

O5—C9	1.330 (3)	C8—C13	1.390 (3)
O6A—N3	1.203 (5)	C8—C14	1.485 (3)
O6B—N3	1.214 (6)	C8—C9	1.409 (3)
O7A—N3	1.268 (5)	C9—C10	1.400 (3)
O7B—N3	1.220 (7)	C10—C11	1.384 (3)
O8—C14	1.256 (3)	C11—C12	1.364 (3)
O5—H5O	0.8200	C12—C13	1.373 (3)
O1—C2	1.331 (3)	C11—H11	0.92 (2)
O2—N1	1.208 (3)	C12—H12	1.00 (3)
O3—N1	1.215 (3)	C13—H13	0.92 (2)
O4—C7	1.251 (3)	C1—C7	1.487 (3)
O1—H1O	0.8200	C1—C2	1.408 (3)
N3—C10	1.462 (3)	C1—C6	1.394 (3)
N4—C14	1.315 (3)	C2—C3	1.405 (3)
N4—H4B	0.91 (3)	C3—C4	1.377 (3)
N4—H4A	0.87 (3)	C4—C5	1.362 (3)
N1—C3	1.459 (3)	C5—C6	1.374 (3)
N2—C7	1.313 (3)	C4—H4	0.90 (2)
N2—H2B	0.93 (3)	C5—H5	0.89 (2)
N2—H2A	0.80 (3)	C6—H6	0.91 (2)
C9—O5—H5O	109.00	O8—C14—N4	120.4 (2)
C2—O1—H1O	109.00	O8—C14—C8	119.73 (19)
O6A—N3—C10	121.8 (3)	C10—C11—H11	120.5 (14)
O7A—N3—C10	116.8 (3)	C12—C11—H11	119.2 (14)
O7B—N3—C10	117.3 (3)	C11—C12—H12	122.5 (14)
O6B—N3—O7B	124.6 (4)	C13—C12—H12	118.2 (14)
O6A—N3—O7A	121.4 (4)	C8—C13—H13	117.7 (14)
O6B—N3—C10	118.1 (3)	C12—C13—H13	120.4 (14)
C14—N4—H4A	120.6 (17)	C6—C1—C7	122.08 (19)
H4A—N4—H4B	116 (2)	C2—C1—C6	119.27 (19)
C14—N4—H4B	123.0 (15)	C2—C1—C7	118.64 (19)
O2—N1—C3	119.37 (18)	O1—C2—C3	120.55 (18)
O3—N1—C3	117.86 (19)	C1—C2—C3	117.33 (19)
O2—N1—O3	122.7 (2)	O1—C2—C1	122.09 (18)
H2A—N2—H2B	120 (2)	N1—C3—C2	120.54 (18)
C7—N2—H2B	117.6 (15)	N1—C3—C4	117.60 (19)
C7—N2—H2A	122.1 (19)	C2—C3—C4	121.9 (2)
C9—C8—C13	119.43 (18)	C3—C4—C5	120.2 (2)
C13—C8—C14	122.27 (19)	C4—C5—C6	119.7 (2)
C9—C8—C14	118.26 (18)	C1—C6—C5	121.6 (2)
O5—C9—C10	120.59 (19)	O4—C7—C1	119.6 (2)
C8—C9—C10	117.21 (19)	N2—C7—C1	120.3 (2)
O5—C9—C8	122.19 (17)	O4—C7—N2	120.1 (2)
N3—C10—C11	117.63 (19)	C3—C4—H4	120.7 (15)
N3—C10—C9	120.55 (19)	C5—C4—H4	119.1 (14)
C9—C10—C11	121.8 (2)	C4—C5—H5	121.6 (15)
C10—C11—C12	120.3 (2)	C6—C5—H5	118.7 (15)
C11—C12—C13	119.3 (2)	C1—C6—H6	118.7 (15)
C8—C13—C12	122.0 (2)	C5—C6—H6	119.6 (15)
N4—C14—C8	119.9 (2)
O6A—N3—C10—C9	−17.2 (5)	C9—C10—C11—C12	−0.6 (3)
O6A—N3—C10—C11	163.1 (4)	N3—C10—C11—C12	179.1 (2)
O7A—N3—C10—C9	163.0 (4)	C10—C11—C12—C13	1.2 (4)
O7A—N3—C10—C11	−16.7 (4)	C11—C12—C13—C8	−0.2 (4)
O2—N1—C3—C2	−30.7 (3)	C6—C1—C2—O1	−179.93 (18)
O2—N1—C3—C4	150.2 (2)	C6—C1—C2—C3	−2.0 (3)
O3—N1—C3—C2	151.1 (2)	C7—C1—C2—O1	−1.3 (3)
O3—N1—C3—C4	−28.0 (3)	C7—C1—C2—C3	176.59 (19)
C13—C8—C9—C10	1.7 (3)	C2—C1—C6—C5	1.0 (3)
C14—C8—C9—O5	−0.7 (3)	C7—C1—C6—C5	−177.5 (2)
C13—C8—C9—O5	−178.57 (19)	C2—C1—C7—O4	−0.5 (3)
C9—C8—C14—N4	175.1 (2)	C2—C1—C7—N2	179.9 (2)
C13—C8—C14—O8	172.1 (2)	C6—C1—C7—O4	178.1 (2)
C13—C8—C14—N4	−7.1 (3)	C6—C1—C7—N2	−1.5 (3)
C14—C8—C13—C12	−179.0 (2)	O1—C2—C3—N1	0.1 (3)
C14—C8—C9—C10	179.55 (18)	O1—C2—C3—C4	179.2 (2)
C9—C8—C13—C12	−1.3 (3)	C1—C2—C3—N1	−177.82 (18)
C9—C8—C14—O8	−5.6 (3)	C1—C2—C3—C4	1.3 (3)
O5—C9—C10—N3	−0.3 (3)	N1—C3—C4—C5	179.7 (2)
O5—C9—C10—C11	179.5 (2)	C2—C3—C4—C5	0.6 (3)
C8—C9—C10—N3	179.46 (18)	C3—C4—C5—C6	−1.7 (4)
C8—C9—C10—C11	−0.8 (3)	C4—C5—C6—C1	0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4	0.82	1.77	2.500 (2)	148
N2—H2A···O6Ai	0.80 (3)	2.38 (3)	3.142 (5)	161 (3)
N2—H2B···O4ii	0.93 (3)	2.03 (3)	2.966 (3)	177 (2)
N4—H4A···O8iii	0.87 (3)	2.07 (3)	2.929 (3)	172 (2)
N4—H4B···O2iv	0.91 (3)	2.18 (3)	3.084 (3)	174 (2)
O5—H5O···O8	0.82	1.76	2.496 (2)	148
C6—H6···O6Ai	0.91 (2)	2.40 (2)	3.285 (6)	163 (2)
C11—H11···O7Av	0.92 (2)	2.41 (2)	3.221 (6)	147 (2)
C11—H11···O7Avi	0.92 (2)	2.55 (2)	2.997 (6)	110.5 (17)
C13—H13···O2iv	0.92 (2)	2.39 (2)	3.289 (3)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O4	0.82	1.77	2.500 (2)	148
N2—H2A⋯O6Ai	0.80 (3)	2.38 (3)	3.142 (5)	161 (3)
N2—H2B⋯O4ii	0.93 (3)	2.03 (3)	2.966 (3)	177 (2)
N4—H4A⋯O8iii	0.87 (3)	2.07 (3)	2.929 (3)	172 (2)
N4—H4B⋯O2iv	0.91 (3)	2.18 (3)	3.084 (3)	174 (2)
O5—H5O⋯O8	0.82	1.76	2.496 (2)	148
C6—H6⋯O6Ai	0.91 (2)	2.40 (2)	3.285 (6)	163 (2)
C11—H11⋯O7Av	0.92 (2)	2.41 (2)	3.221 (6)	147 (2)
C11—H11⋯O7Avi	0.92 (2)	2.55 (2)	2.997 (6)	110.5 (17)
C13—H13⋯O2iv	0.92 (2)	2.39 (2)	3.289 (3)	165 (2)

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