2-Amino-3-chloro-5-nitro-benzamide.

The amide group in the title compound, C(7)H(6)ClN(3)O(3), is significantly twisted out of the plane of the benzene ring [C-C-C-O = 34.2 (5)°] whereas the nitro group is almost co-planar [O-N-C-C = 4.0 (5)°] with the ring. Intra-molecular N-H⋯O and N-H⋯Cl hydrogen bonds occur. In the crystal, the mol-ecules are linked by N-H⋯O hydrogen bonds, generating layers propagating in the ab plane.

Related literature

For crystal engineering studies on related mol­ecules, see: Wardell & Tiekink (2011 ▶).

Experimental

Crystal data

C7H6ClN3O3

M = 215.60

Triclinic,

a = 4.891 (9) Å

b = 6.363 (13) Å

c = 14.61 (3) Å

α = 83.54 (11)°

β = 82.37 (11)°

γ = 73.64 (9)°

V = 431.1 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.43 mm−1

T = 100 K

0.18 × 0.08 × 0.01 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011 ▶) T min = 0.826, T max = 1.000

3828 measured reflections

1936 independent reflections

1104 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.180

S = 0.95

1936 reflections

139 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.80 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2011 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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 DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009142/hb6665sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009142/hb6665Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009142/hb6665Isup3.cml

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

C7H6ClN3O3	Z = 2
Mr = 215.60	F(000) = 220
Triclinic, P1	Dx = 1.661 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.891 (9) Å	Cell parameters from 1104 reflections
b = 6.363 (13) Å	θ = 2.8–30.7°
c = 14.61 (3) Å	µ = 0.43 mm−1
α = 83.54 (11)°	T = 100 K
β = 82.37 (11)°	Plate, yellow
γ = 73.64 (9)°	0.18 × 0.08 × 0.01 mm
V = 431.1 (15) Å3

Rigaku Saturn724+ diffractometer	1936 independent reflections
Radiation source: Rotating Anode	1104 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.048
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 2.8°
profile data from ω–scans	h = −4→6
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011)	k = −7→8
Tmin = 0.826, Tmax = 1.000	l = −18→18
3828 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0912P)2] where P = (Fo2 + 2Fc2)/3
1936 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.44 e Å−3
4 restraints	Δρmin = −0.80 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	0.2620 (2)	0.75410 (16)	0.44557 (7)	0.0290 (3)
O1	0.2845 (5)	0.6916 (4)	0.07122 (19)	0.0270 (7)
O2	0.8552 (6)	1.3190 (4)	0.32947 (19)	0.0265 (7)
O3	0.9263 (5)	1.3326 (4)	0.17747 (18)	0.0258 (7)
N1	0.7241 (7)	0.7345 (5)	0.0176 (2)	0.0224 (7)
H1N	0.731 (8)	0.659 (6)	−0.0305 (18)	0.027*
H2N	0.892 (4)	0.753 (6)	0.024 (3)	0.027*
N2	0.2414 (7)	0.6089 (5)	0.2610 (2)	0.0230 (7)
H3N	0.201 (8)	0.579 (6)	0.2079 (15)	0.028*
H4N	0.162 (8)	0.570 (6)	0.3155 (14)	0.028*
N3	0.8307 (6)	1.2566 (5)	0.2533 (2)	0.0203 (7)
C1	0.5172 (7)	0.8433 (6)	0.1718 (3)	0.0198 (8)
C2	0.3850 (8)	0.7644 (6)	0.2572 (3)	0.0218 (8)
C3	0.4161 (8)	0.8510 (6)	0.3398 (3)	0.0230 (9)
C4	0.5587 (8)	1.0104 (6)	0.3399 (3)	0.0224 (8)
H4	0.5744	1.0662	0.3961	0.027*
C5	0.6798 (7)	1.0873 (6)	0.2546 (3)	0.0197 (8)
C6	0.6623 (8)	1.0049 (6)	0.1714 (3)	0.0221 (8)
H6	0.7485	1.0581	0.1148	0.026*
C7	0.5010 (8)	0.7488 (6)	0.0829 (3)	0.0219 (8)

	U11	U22	U33	U12	U13	U23
Cl1	0.0357 (6)	0.0244 (6)	0.0280 (5)	−0.0122 (4)	0.0008 (4)	−0.0015 (4)
O1	0.0219 (14)	0.0255 (15)	0.0363 (16)	−0.0106 (12)	0.0018 (12)	−0.0093 (12)
O2	0.0323 (15)	0.0245 (15)	0.0253 (15)	−0.0098 (12)	−0.0041 (12)	−0.0064 (12)
O3	0.0286 (15)	0.0220 (15)	0.0270 (15)	−0.0104 (12)	0.0033 (12)	−0.0004 (12)
N1	0.0213 (16)	0.0209 (18)	0.0262 (17)	−0.0059 (14)	−0.0019 (14)	−0.0071 (14)
N2	0.0253 (17)	0.0171 (17)	0.0272 (18)	−0.0077 (14)	−0.0025 (15)	0.0006 (14)
N3	0.0173 (15)	0.0145 (16)	0.0282 (17)	−0.0025 (12)	−0.0022 (13)	−0.0027 (13)
C1	0.0157 (17)	0.0131 (18)	0.028 (2)	−0.0002 (14)	−0.0007 (15)	−0.0016 (15)
C2	0.0187 (18)	0.0106 (18)	0.032 (2)	0.0006 (14)	0.0001 (16)	−0.0020 (15)
C3	0.0200 (18)	0.0158 (19)	0.031 (2)	0.0000 (15)	−0.0067 (16)	−0.0017 (16)
C4	0.0234 (19)	0.0141 (18)	0.028 (2)	−0.0018 (15)	−0.0011 (16)	−0.0040 (16)
C5	0.0162 (17)	0.0134 (18)	0.028 (2)	−0.0022 (14)	−0.0029 (15)	−0.0008 (15)
C6	0.0216 (18)	0.0149 (19)	0.026 (2)	−0.0007 (15)	0.0015 (16)	0.0003 (15)
C7	0.0241 (19)	0.0147 (18)	0.025 (2)	−0.0037 (15)	0.0018 (16)	−0.0041 (15)

Cl1—C3	1.753 (5)	N3—C5	1.464 (5)
O1—C7	1.250 (5)	C1—C6	1.403 (5)
O2—N3	1.254 (4)	C1—C2	1.433 (5)
O3—N3	1.244 (4)	C1—C7	1.511 (6)
N1—C7	1.340 (5)	C2—C3	1.425 (6)
N1—H1N	0.887 (10)	C3—C4	1.383 (6)
N1—H2N	0.881 (10)	C4—C5	1.406 (6)
N2—C2	1.358 (5)	C4—H4	0.9500
N2—H3N	0.881 (10)	C5—C6	1.398 (6)
N2—H4N	0.881 (10)	C6—H6	0.9500
C7—N1—H1N	118 (3)	C4—C3—C2	122.8 (4)
C7—N1—H2N	127 (3)	C4—C3—Cl1	118.7 (3)
H1N—N1—H2N	112 (4)	C2—C3—Cl1	118.4 (3)
C2—N2—H3N	117 (3)	C3—C4—C5	118.1 (4)
C2—N2—H4N	118 (3)	C3—C4—H4	121.0
H3N—N2—H4N	124 (4)	C5—C4—H4	121.0
O3—N3—O2	123.2 (3)	C6—C5—C4	121.7 (4)
O3—N3—C5	119.0 (3)	C6—C5—N3	119.4 (3)
O2—N3—C5	117.8 (3)	C4—C5—N3	118.9 (3)
C6—C1—C2	120.0 (4)	C5—C6—C1	119.9 (4)
C6—C1—C7	120.7 (3)	C5—C6—H6	120.0
C2—C1—C7	119.3 (3)	C1—C6—H6	120.0
N2—C2—C3	120.4 (4)	O1—C7—N1	122.2 (4)
N2—C2—C1	122.2 (4)	O1—C7—C1	120.6 (3)
C3—C2—C1	117.4 (4)	N1—C7—C1	117.2 (3)
C6—C1—C2—N2	179.8 (3)	O3—N3—C5—C6	4.0 (5)
C7—C1—C2—N2	−1.0 (5)	O2—N3—C5—C6	−176.4 (3)
C6—C1—C2—C3	−2.0 (5)	O3—N3—C5—C4	−176.6 (3)
C7—C1—C2—C3	177.3 (3)	O2—N3—C5—C4	2.9 (5)
N2—C2—C3—C4	−179.6 (3)	C4—C5—C6—C1	1.0 (5)
C1—C2—C3—C4	2.1 (5)	N3—C5—C6—C1	−179.7 (3)
N2—C2—C3—Cl1	−0.6 (5)	C2—C1—C6—C5	0.5 (5)
C1—C2—C3—Cl1	−178.9 (3)	C7—C1—C6—C5	−178.7 (3)
C2—C3—C4—C5	−0.7 (6)	C6—C1—C7—O1	−146.6 (4)
Cl1—C3—C4—C5	−179.7 (3)	C2—C1—C7—O1	34.2 (5)
C3—C4—C5—C6	−0.9 (5)	C6—C1—C7—N1	31.9 (5)
C3—C4—C5—N3	179.8 (3)	C2—C1—C7—N1	−147.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H3n···O1	0.88 (3)	2.07 (2)	2.755 (7)	134 (3)
N2—H4n···Cl1	0.88 (2)	2.51 (3)	2.970 (7)	113 (3)
N1—H1n···O1i	0.89 (3)	2.40 (4)	3.148 (8)	143 (3)
N1—H1n···O3ii	0.89 (3)	2.55 (3)	3.130 (8)	124 (3)
N1—H2n···O1iii	0.88 (2)	2.05 (3)	2.881 (7)	158 (4)
N2—H3n···O3iv	0.88 (3)	2.44 (4)	3.076 (8)	130 (3)
N2—H4n···O2iv	0.88 (2)	2.46 (4)	3.003 (8)	121 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H3n⋯O1	0.88 (3)	2.07 (2)	2.755 (7)	134 (3)
N2—H4n⋯Cl1	0.88 (2)	2.51 (3)	2.970 (7)	113 (3)
N1—H1n⋯O1i	0.89 (3)	2.40 (4)	3.148 (8)	143 (3)
N1—H1n⋯O3ii	0.89 (3)	2.55 (3)	3.130 (8)	124 (3)
N1—H2n⋯O1iii	0.88 (2)	2.05 (3)	2.881 (7)	158 (4)
N2—H3n⋯O3iv	0.88 (3)	2.44 (4)	3.076 (8)	130 (3)
N2—H4n⋯O2iv	0.88 (2)	2.46 (4)	3.003 (8)	121 (3)

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