3-Nitro-benzene-1,2-diamine.

The mol-ecule of the title compound, C(6)H(7)N(3)O(2), a derivative of o-phenyl-enediamine, nearly shows non-crystallographic C(s) symmetry. C-C-C angles span the range 116.25 (11)-122.35 (11)°. In the crystal, inter-molecular N-H⋯O and N-H⋯N hydrogen bonds connect mol-ecules into undulating sheets perpendicular to the crystallographic a axis. A weak intra-molecular N-H⋯O hydrogen bond is also observed. No π-stacking is observed in the crystal structure.

Related literature

For the crystal structure of 1,2-diamino­benzene, see: Stalhandske (1981 ▶); Czapik & Gdaniec (2010 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For the use of chelate ligands in coordination chemistry, see: Gade (1998 ▶). For the crystal structures of coordination compounds with rhenium in different oxidation states applying (mixed) oxygen-, nitro­gen- and/or sulfur-containing ligands, see: Chiozzone et al. (1999 ▶); Videira et al. (2009 ▶); Edwards et al. (1998 ▶); Marti et al. (2005 ▶); Babich et al. (2001 ▶).

Experimental

Crystal data

C6H7N3O2

M = 153.15

Monoclinic,

a = 13.2854 (5) Å

b = 3.7504 (1) Å

c = 16.3309 (6) Å

β = 126.208 (2)°

V = 656.55 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 200 K

0.55 × 0.24 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

6477 measured reflections

1605 independent reflections

1262 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.115

S = 1.05

1605 reflections

113 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); 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 Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016825/sj5135sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016825/sj5135Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016825/sj5135Isup3.cml

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

C6H7N3O2	F(000) = 320
Mr = 153.15	Dx = 1.549 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3115 reflections
a = 13.2854 (5) Å	θ = 2.5–28.2°
b = 3.7504 (1) Å	µ = 0.12 mm−1
c = 16.3309 (6) Å	T = 200 K
β = 126.208 (2)°	Rod, red
V = 656.55 (4) Å3	0.55 × 0.24 × 0.11 mm
Z = 4

Bruker APEXII CCD diffractometer	1262 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
graphite	θmax = 28.3°, θmin = 3.1°
φ and ω scans	h = −17→17
6477 measured reflections	k = −4→4
1605 independent reflections	l = −21→21

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.055P)2 + 0.1822P] where P = (Fo2 + 2Fc2)/3
1605 reflections	(Δ/σ)max < 0.001
113 parameters	Δρmax = 0.30 e Å−3
6 restraints	Δρmin = −0.17 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.13915 (10)	0.7321 (4)	0.03335 (7)	0.0524 (3)
O2	0.30745 (12)	1.0010 (4)	0.07783 (10)	0.0687 (4)
N1	0.13706 (12)	0.8731 (4)	0.34249 (9)	0.0419 (3)
H711	0.1778 (16)	0.888 (5)	0.4092 (10)	0.063*
H712	0.1066 (16)	0.649 (4)	0.3250 (14)	0.063*
N2	0.07013 (10)	0.7189 (3)	0.15331 (8)	0.0346 (3)
H721	0.0209 (14)	0.662 (5)	0.1708 (12)	0.052*
H722	0.0458 (15)	0.663 (5)	0.0919 (10)	0.052*
N3	0.23536 (11)	0.9000 (3)	0.09715 (8)	0.0382 (3)
C1	0.22068 (11)	0.9559 (3)	0.31843 (9)	0.0289 (3)
C2	0.18152 (10)	0.8773 (3)	0.21809 (8)	0.0241 (3)
C3	0.26459 (10)	0.9743 (3)	0.19499 (8)	0.0268 (3)
C4	0.37907 (11)	1.1429 (3)	0.26574 (11)	0.0349 (3)
H4	0.4329	1.2060	0.2477	0.042*
C5	0.41227 (12)	1.2152 (4)	0.36057 (10)	0.0397 (3)
H5	0.4895	1.3289	0.4091	0.048*
C6	0.33235 (12)	1.1214 (4)	0.38622 (9)	0.0374 (3)
H6	0.3561	1.1739	0.4524	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0500 (6)	0.0787 (8)	0.0285 (5)	−0.0038 (6)	0.0231 (5)	−0.0108 (5)
O2	0.0701 (8)	0.1063 (11)	0.0630 (7)	−0.0052 (7)	0.0575 (7)	0.0026 (7)
N1	0.0512 (7)	0.0525 (8)	0.0371 (6)	0.0146 (6)	0.0344 (6)	0.0103 (6)
N2	0.0294 (5)	0.0433 (7)	0.0331 (5)	−0.0028 (4)	0.0195 (5)	−0.0030 (5)
N3	0.0430 (6)	0.0493 (7)	0.0343 (6)	0.0089 (5)	0.0294 (5)	0.0054 (5)
C1	0.0353 (6)	0.0286 (6)	0.0263 (5)	0.0121 (5)	0.0201 (5)	0.0066 (5)
C2	0.0261 (5)	0.0237 (5)	0.0244 (5)	0.0061 (4)	0.0160 (4)	0.0031 (4)
C3	0.0299 (6)	0.0276 (6)	0.0264 (5)	0.0052 (4)	0.0185 (5)	0.0035 (4)
C4	0.0300 (6)	0.0283 (6)	0.0472 (7)	0.0024 (5)	0.0233 (6)	0.0037 (5)
C5	0.0305 (6)	0.0294 (7)	0.0404 (7)	0.0011 (5)	0.0106 (5)	−0.0050 (5)
C6	0.0433 (7)	0.0331 (7)	0.0249 (6)	0.0114 (5)	0.0140 (5)	−0.0011 (5)

O1—N3	1.2420 (16)	C1—C6	1.3681 (18)
O2—N3	1.2318 (15)	C1—C2	1.4268 (15)
N1—C1	1.4142 (16)	C2—C3	1.4088 (15)
N1—H711	0.887 (12)	C3—C4	1.4041 (17)
N1—H712	0.903 (12)	C4—C5	1.364 (2)
N2—C2	1.3462 (15)	C4—H4	0.9500
N2—H721	0.880 (12)	C5—C6	1.397 (2)
N2—H722	0.878 (12)	C5—H5	0.9500
N3—C3	1.4313 (15)	C6—H6	0.9500
C1—N1—H711	108.5 (12)	C3—C2—C1	116.25 (11)
C1—N1—H712	113.3 (12)	C4—C3—C2	122.35 (11)
H711—N1—H712	106.4 (15)	C4—C3—N3	117.01 (11)
C2—N2—H721	122.3 (11)	C2—C3—N3	120.64 (11)
C2—N2—H722	119.6 (11)	C5—C4—C3	119.38 (12)
H721—N2—H722	118.0 (14)	C5—C4—H4	120.3
O2—N3—O1	120.77 (12)	C3—C4—H4	120.3
O2—N3—C3	119.13 (12)	C4—C5—C6	119.81 (12)
O1—N3—C3	120.09 (10)	C4—C5—H5	120.1
C6—C1—N1	121.95 (11)	C6—C5—H5	120.1
C6—C1—C2	120.56 (11)	C1—C6—C5	121.65 (12)
N1—C1—C2	117.41 (11)	C1—C6—H6	119.2
N2—C2—C3	125.10 (10)	C5—C6—H6	119.2
N2—C2—C1	118.65 (10)
C6—C1—C2—N2	−179.04 (11)	O1—N3—C3—C4	175.60 (12)
N1—C1—C2—N2	−2.26 (17)	O2—N3—C3—C2	177.07 (12)
C6—C1—C2—C3	0.96 (17)	O1—N3—C3—C2	−3.77 (19)
N1—C1—C2—C3	177.74 (10)	C2—C3—C4—C5	0.29 (19)
N2—C2—C3—C4	179.27 (11)	N3—C3—C4—C5	−179.07 (11)
C1—C2—C3—C4	−0.73 (17)	C3—C4—C5—C6	−0.04 (19)
N2—C2—C3—N3	−1.39 (19)	N1—C1—C6—C5	−177.40 (12)
C1—C2—C3—N3	178.60 (10)	C2—C1—C6—C5	−0.78 (19)
O2—N3—C3—C4	−3.56 (19)	C4—C5—C6—C1	0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H711···O1i	0.89 (1)	2.41 (2)	3.1257 (14)	138.(2)
N2—H721···N1ii	0.88 (1)	2.26 (1)	3.0800 (16)	156.(2)
N2—H722···O1	0.88 (1)	1.98 (1)	2.6084 (14)	127.(1)
N2—H722···O1iii	0.88 (1)	2.55 (2)	3.1416 (16)	126.(1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H711⋯O1i	0.89 (1)	2.41 (2)	3.1257 (14)	138 (2)
N2—H721⋯N1ii	0.88 (1)	2.26 (1)	3.0800 (16)	156 (2)
N2—H722⋯O1	0.88 (1)	1.98 (1)	2.6084 (14)	127 (1)
N2—H722⋯O1iii	0.88 (1)	2.55 (2)	3.1416 (16)	126 (1)

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