N-(4-Chloro-phen-yl)-3-nitro-pyridin-2-amine.

In the title compound, C(11)H(8)ClN(3)O(2), the presence of intra-molecular N-H⋯O and C-H⋯N inter-actions help to establish an almost planar mol-ecule [dihedral angle between the pyridine and benzene rings = 9.89 (8)° and r.m.s. deviation for all 17 non-H atoms = 0.120 Å]. Supra-molecular tapes feature in the crystal packing whereby dimeric aggregates sustained by pairs of C-H⋯O inter-actions are connected by π-π inter-actions occurring between translationally related pyridine rings and between translationally related benzene rings along the b axis [centroid-centroid distance = length of b axis = 3.8032 (4) Å].

Related literature

For the structure of a related pyrimidine amine derivative, see: Aznan Akhmad et al. (2010 ▶).

Experimental

Crystal data

C11H8ClN3O2

M = 249.65

Monoclinic,

a = 30.472 (3) Å

b = 3.8032 (4) Å

c = 21.300 (2) Å

β = 123.153 (1)°

V = 2066.7 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.36 mm−1

T = 100 K

0.40 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.869, T max = 0.982

8919 measured reflections

2347 independent reflections

1912 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.091

S = 1.00

2347 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811045570/hb6473sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045570/hb6473Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045570/hb6473Isup3.cml

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

C11H8ClN3O2	F(000) = 1024
Mr = 249.65	Dx = 1.605 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2586 reflections
a = 30.472 (3) Å	θ = 2.3–28.0°
b = 3.8032 (4) Å	µ = 0.36 mm−1
c = 21.300 (2) Å	T = 100 K
β = 123.153 (1)°	Prism, red-brown
V = 2066.7 (4) Å3	0.40 × 0.15 × 0.05 mm
Z = 8

Bruker SMART APEX CCD diffractometer	2347 independent reflections
Radiation source: fine-focus sealed tube	1912 reflections with I > 2σ(I)
graphite	Rint = 0.042
ω scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→38
Tmin = 0.869, Tmax = 0.982	k = −4→4
8919 measured reflections	l = −27→27

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0483P)2 + 1.1995P] where P = (Fo2 + 2Fc2)/3
2347 reflections	(Δ/σ)max = 0.001
158 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	0.223442 (15)	0.15167 (11)	0.28841 (2)	0.01760 (13)
O1	0.00287 (5)	1.1095 (3)	0.32850 (6)	0.0239 (3)
O2	−0.01657 (5)	1.3711 (4)	0.40019 (7)	0.0271 (3)
N1	0.09477 (5)	0.8069 (4)	0.38672 (8)	0.0151 (3)
H1n	0.0640 (8)	0.866 (5)	0.3481 (11)	0.021 (5)*
N2	0.14771 (5)	0.8205 (4)	0.51652 (7)	0.0155 (3)
N3	0.01356 (5)	1.1930 (4)	0.39171 (8)	0.0180 (3)
C1	0.10203 (6)	0.9037 (4)	0.45291 (9)	0.0141 (3)
C2	0.06265 (6)	1.0832 (4)	0.45711 (9)	0.0148 (3)
C3	0.07133 (7)	1.1672 (4)	0.52649 (9)	0.0175 (3)
H3	0.0452	1.2859	0.5296	0.021*
C4	0.11814 (7)	1.0768 (4)	0.59046 (9)	0.0181 (4)
H4	0.1252	1.1299	0.6388	0.022*
C5	0.15475 (6)	0.9047 (4)	0.58188 (9)	0.0172 (3)
H5	0.1872	0.8427	0.6261	0.021*
C6	0.12870 (6)	0.6443 (4)	0.36965 (9)	0.0137 (3)
C7	0.18163 (6)	0.5712 (4)	0.42051 (9)	0.0161 (3)
H7	0.1978	0.6249	0.4722	0.019*
C8	0.21055 (6)	0.4195 (4)	0.39510 (9)	0.0163 (3)
H8	0.2467	0.3708	0.4294	0.020*
C9	0.18699 (6)	0.3393 (4)	0.32026 (9)	0.0149 (3)
C10	0.13421 (6)	0.4065 (4)	0.26931 (9)	0.0161 (3)
H10	0.1181	0.3478	0.2179	0.019*
C11	0.10550 (6)	0.5593 (4)	0.29426 (9)	0.0158 (3)
H11	0.0694	0.6076	0.2596	0.019*

	U11	U22	U33	U12	U13	U23
Cl1	0.0176 (2)	0.0184 (2)	0.0213 (2)	0.00078 (16)	0.01348 (17)	−0.00104 (16)
O1	0.0167 (6)	0.0340 (8)	0.0164 (6)	0.0051 (5)	0.0062 (5)	−0.0024 (5)
O2	0.0182 (6)	0.0350 (8)	0.0279 (7)	0.0118 (6)	0.0125 (5)	−0.0006 (6)
N1	0.0103 (7)	0.0182 (7)	0.0148 (6)	0.0020 (6)	0.0056 (6)	−0.0004 (6)
N2	0.0130 (7)	0.0168 (7)	0.0157 (6)	0.0005 (6)	0.0071 (6)	0.0011 (5)
N3	0.0148 (7)	0.0186 (7)	0.0213 (7)	0.0018 (6)	0.0103 (6)	−0.0002 (6)
C1	0.0148 (8)	0.0107 (8)	0.0176 (7)	−0.0025 (6)	0.0094 (6)	−0.0004 (6)
C2	0.0115 (8)	0.0141 (8)	0.0184 (8)	−0.0007 (6)	0.0079 (6)	−0.0003 (6)
C3	0.0197 (8)	0.0143 (8)	0.0234 (8)	0.0004 (7)	0.0148 (7)	0.0006 (6)
C4	0.0225 (9)	0.0167 (8)	0.0178 (8)	−0.0018 (7)	0.0128 (7)	−0.0008 (6)
C5	0.0157 (8)	0.0178 (9)	0.0161 (7)	−0.0009 (7)	0.0073 (6)	0.0013 (6)
C6	0.0145 (8)	0.0104 (8)	0.0178 (7)	−0.0013 (6)	0.0098 (6)	0.0000 (6)
C7	0.0157 (8)	0.0170 (8)	0.0152 (7)	−0.0004 (7)	0.0082 (7)	−0.0016 (6)
C8	0.0115 (8)	0.0174 (8)	0.0183 (8)	0.0000 (6)	0.0070 (6)	−0.0001 (6)
C9	0.0168 (8)	0.0114 (8)	0.0206 (8)	0.0000 (6)	0.0129 (7)	0.0004 (6)
C10	0.0163 (8)	0.0158 (8)	0.0149 (7)	−0.0015 (6)	0.0078 (6)	−0.0006 (6)
C11	0.0129 (8)	0.0148 (8)	0.0169 (7)	−0.0004 (6)	0.0065 (6)	0.0003 (6)

Cl1—C9	1.7400 (16)	C4—C5	1.389 (2)
O1—N3	1.2408 (18)	C4—H4	0.9500
O2—N3	1.2312 (18)	C5—H5	0.9500
N1—C1	1.353 (2)	C6—C11	1.393 (2)
N1—C6	1.412 (2)	C6—C7	1.393 (2)
N1—H1n	0.87 (2)	C7—C8	1.387 (2)
N2—C5	1.327 (2)	C7—H7	0.9500
N2—C1	1.346 (2)	C8—C9	1.378 (2)
N3—C2	1.440 (2)	C8—H8	0.9500
C1—C2	1.426 (2)	C9—C10	1.386 (2)
C2—C3	1.389 (2)	C10—C11	1.376 (2)
C3—C4	1.372 (2)	C10—H10	0.9500
C3—H3	0.9500	C11—H11	0.9500
C1—N1—C6	131.43 (14)	N2—C5—H5	117.6
C1—N1—H1n	113.1 (12)	C4—C5—H5	117.6
C6—N1—H1n	115.4 (12)	C11—C6—C7	119.45 (15)
C5—N2—C1	118.99 (14)	C11—C6—N1	114.64 (14)
O2—N3—O1	121.71 (14)	C7—C6—N1	125.90 (14)
O2—N3—C2	118.75 (13)	C8—C7—C6	119.47 (14)
O1—N3—C2	119.54 (13)	C8—C7—H7	120.3
N2—C1—N1	118.36 (14)	C6—C7—H7	120.3
N2—C1—C2	119.48 (14)	C9—C8—C7	120.22 (15)
N1—C1—C2	122.15 (14)	C9—C8—H8	119.9
C3—C2—C1	120.01 (15)	C7—C8—H8	119.9
C3—C2—N3	117.09 (14)	C8—C9—C10	120.84 (15)
C1—C2—N3	122.88 (14)	C8—C9—Cl1	120.15 (13)
C4—C3—C2	119.25 (15)	C10—C9—Cl1	119.02 (12)
C4—C3—H3	120.4	C11—C10—C9	119.08 (15)
C2—C3—H3	120.4	C11—C10—H10	120.5
C3—C4—C5	117.45 (15)	C9—C10—H10	120.5
C3—C4—H4	121.3	C10—C11—C6	120.93 (15)
C5—C4—H4	121.3	C10—C11—H11	119.5
N2—C5—C4	124.83 (15)	C6—C11—H11	119.5
C5—N2—C1—N1	−178.05 (15)	C1—N2—C5—C4	−0.2 (3)
C5—N2—C1—C2	0.7 (2)	C3—C4—C5—N2	−0.2 (3)
C6—N1—C1—N2	−4.5 (3)	C1—N1—C6—C11	175.03 (16)
C6—N1—C1—C2	176.74 (16)	C1—N1—C6—C7	−6.0 (3)
N2—C1—C2—C3	−0.7 (2)	C11—C6—C7—C8	0.9 (2)
N1—C1—C2—C3	177.97 (16)	N1—C6—C7—C8	−178.01 (15)
N2—C1—C2—N3	177.63 (14)	C6—C7—C8—C9	−0.5 (3)
N1—C1—C2—N3	−3.7 (3)	C7—C8—C9—C10	−0.3 (3)
O2—N3—C2—C3	4.2 (2)	C7—C8—C9—Cl1	179.57 (13)
O1—N3—C2—C3	−176.53 (15)	C8—C9—C10—C11	0.8 (2)
O2—N3—C2—C1	−174.27 (15)	Cl1—C9—C10—C11	−179.10 (13)
O1—N3—C2—C1	5.0 (2)	C9—C10—C11—C6	−0.4 (3)
C1—C2—C3—C4	0.3 (3)	C7—C6—C11—C10	−0.4 (2)
N3—C2—C3—C4	−178.19 (15)	N1—C6—C11—C10	178.60 (15)
C2—C3—C4—C5	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1	0.87 (2)	1.91 (2)	2.6280 (18)	138.2 (17)
C7—H7···N2	0.95	2.31	2.909 (2)	120
C3—H3···O2i	0.95	2.48	3.340 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1	0.87 (2)	1.91 (2)	2.6280 (18)	138.2 (17)
C7—H7⋯N2	0.95	2.31	2.909 (2)	120
C3—H3⋯O2i	0.95	2.48	3.340 (3)	152

Symmetry code: (i) .