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

The dihedral angle between the benzene and pyridyl rings in the title compound, C(11)H(8)ClN(3)O(2), is 22.65 (10)°, indicating a twisted mol-ecule. The amine H and nitro O atoms form a donor-acceptor pair for an intra-molecular N-H⋯O hydrogen bond so that the nitro group is almost coplanar with the pyridine ring to which it is connected [O-N-C-C torsion angle = 7.4 (3)°]. The pyridine N and Cl atoms are approximately syn. The crystal packing features C-H⋯Cl inter-actions that lead to undulating supra-molecular chains along [101]. These are connected into sheets by π-π inter-actions occurring between the benzene rings and between the pyridine rings of translationally related mol-ecules along the b axis [centroid-centroid distances = length of b axis = 3.7157 (2) 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 = 15.8781 (10) Å

b = 3.7157 (2) Å

c = 18.0651 (13) Å

β = 102.252 (6)°

V = 1041.53 (11) Å3

Z = 4

Cu Kα radiation

μ = 3.21 mm−1

T = 100 K

0.20 × 0.05 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.566, T max = 0.910

3341 measured reflections

1971 independent reflections

1684 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.119

S = 1.06

1971 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536811044011/hb6466sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044011/hb6466Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044011/hb6466Isup3.cml

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

C11H8ClN3O2	F(000) = 512
Mr = 249.65	Dx = 1.592 Mg m−3
Monoclinic, P2/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yac	Cell parameters from 1441 reflections
a = 15.8781 (10) Å	θ = 2.9–74.2°
b = 3.7157 (2) Å	µ = 3.21 mm−1
c = 18.0651 (13) Å	T = 100 K
β = 102.252 (6)°	Prism, orange
V = 1041.53 (11) Å3	0.20 × 0.05 × 0.03 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	1971 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1684 reflections with I > 2σ(I)
Mirror	Rint = 0.026
Detector resolution: 10.4041 pixels mm-1	θmax = 70.0°, θmin = 3.4°
ω scan	h = −19→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −4→2
Tmin = 0.566, Tmax = 0.910	l = −22→20
3341 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0688P)2 + 0.3527P] where P = (Fo2 + 2Fc2)/3
1971 reflections	(Δ/σ)max = 0.001
158 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.34 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 > 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
Cl1	0.78774 (3)	0.02226 (14)	0.66591 (3)	0.02816 (19)
O1	0.66072 (10)	0.4237 (5)	0.23466 (9)	0.0357 (4)
O2	0.54073 (10)	0.6787 (5)	0.18194 (9)	0.0348 (4)
N1	0.68353 (11)	0.1981 (5)	0.37651 (10)	0.0227 (4)
N2	0.55898 (11)	0.1975 (5)	0.42492 (9)	0.0221 (4)
N3	0.58523 (12)	0.5144 (5)	0.23471 (10)	0.0259 (4)
C1	0.74388 (13)	0.0748 (6)	0.44066 (12)	0.0217 (4)
C2	0.73308 (13)	0.1013 (5)	0.51495 (12)	0.0214 (4)
H2	0.6815	0.1947	0.5261	0.026*
C3	0.80060 (14)	−0.0138 (5)	0.57217 (12)	0.0225 (5)
C4	0.87682 (14)	−0.1519 (6)	0.55902 (13)	0.0258 (5)
H4	0.9216	−0.2272	0.5997	0.031*
C5	0.88592 (14)	−0.1769 (6)	0.48458 (12)	0.0268 (5)
H5	0.9376	−0.2719	0.4738	0.032*
C6	0.82038 (14)	−0.0648 (6)	0.42579 (13)	0.0245 (5)
H6	0.8274	−0.0828	0.3750	0.029*
C7	0.59821 (13)	0.2730 (5)	0.36741 (11)	0.0205 (4)
C8	0.54874 (14)	0.4251 (6)	0.29929 (11)	0.0213 (4)
C9	0.46195 (14)	0.4956 (5)	0.29291 (12)	0.0228 (5)
H9	0.4289	0.5972	0.2477	0.027*
C10	0.42391 (13)	0.4171 (6)	0.35261 (12)	0.0237 (5)
H10	0.3646	0.4644	0.3500	0.028*
C11	0.47531 (13)	0.2665 (6)	0.41660 (11)	0.0239 (5)
H11	0.4489	0.2081	0.4576	0.029*
H1n	0.7042 (17)	0.237 (8)	0.3359 (15)	0.041 (8)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0287 (3)	0.0341 (3)	0.0202 (3)	−0.0026 (2)	0.0018 (2)	0.0004 (2)
O1	0.0280 (8)	0.0557 (11)	0.0255 (9)	0.0049 (8)	0.0110 (7)	0.0076 (8)
O2	0.0308 (8)	0.0474 (10)	0.0249 (9)	0.0005 (8)	0.0030 (7)	0.0135 (8)
N1	0.0213 (8)	0.0297 (9)	0.0180 (9)	0.0012 (7)	0.0060 (7)	0.0031 (8)
N2	0.0238 (9)	0.0234 (8)	0.0194 (9)	−0.0014 (7)	0.0054 (7)	−0.0001 (7)
N3	0.0267 (10)	0.0301 (10)	0.0214 (10)	−0.0029 (8)	0.0061 (8)	0.0015 (8)
C1	0.0215 (10)	0.0202 (9)	0.0225 (11)	−0.0019 (8)	0.0025 (8)	0.0005 (8)
C2	0.0207 (10)	0.0193 (9)	0.0242 (11)	−0.0010 (8)	0.0049 (8)	0.0001 (8)
C3	0.0249 (10)	0.0184 (10)	0.0229 (11)	−0.0052 (8)	0.0020 (8)	−0.0003 (8)
C4	0.0230 (10)	0.0223 (10)	0.0294 (12)	0.0000 (9)	−0.0007 (8)	0.0018 (9)
C5	0.0221 (10)	0.0254 (10)	0.0327 (12)	0.0026 (9)	0.0055 (9)	−0.0006 (9)
C6	0.0257 (11)	0.0232 (10)	0.0256 (11)	−0.0004 (9)	0.0078 (9)	−0.0021 (8)
C7	0.0215 (10)	0.0186 (9)	0.0217 (10)	−0.0008 (8)	0.0057 (8)	−0.0017 (8)
C8	0.0255 (10)	0.0211 (9)	0.0177 (10)	−0.0020 (8)	0.0056 (8)	0.0004 (8)
C9	0.0231 (10)	0.0211 (10)	0.0224 (11)	0.0002 (8)	0.0008 (8)	−0.0001 (8)
C10	0.0198 (10)	0.0239 (10)	0.0275 (11)	−0.0005 (8)	0.0055 (8)	−0.0036 (9)
C11	0.0259 (10)	0.0243 (11)	0.0234 (11)	−0.0028 (9)	0.0097 (8)	−0.0026 (9)

Cl1—C3	1.753 (2)	C3—C4	1.381 (3)
O1—N3	1.245 (2)	C4—C5	1.386 (3)
O2—N3	1.222 (2)	C4—H4	0.9500
N1—C7	1.358 (3)	C5—C6	1.384 (3)
N1—C1	1.414 (3)	C5—H5	0.9500
N1—H1n	0.88 (3)	C6—H6	0.9500
N2—C11	1.330 (3)	C7—C8	1.428 (3)
N2—C7	1.349 (3)	C8—C9	1.383 (3)
N3—C8	1.447 (3)	C9—C10	1.374 (3)
C1—C2	1.392 (3)	C9—H9	0.9500
C1—C6	1.398 (3)	C10—C11	1.384 (3)
C2—C3	1.389 (3)	C10—H10	0.9500
C2—H2	0.9500	C11—H11	0.9500
C7—N1—C1	130.58 (17)	C6—C5—H5	119.7
C7—N1—H1n	113.9 (18)	C4—C5—H5	119.7
C1—N1—H1n	115.5 (18)	C5—C6—C1	120.4 (2)
C11—N2—C7	119.09 (18)	C5—C6—H6	119.8
O2—N3—O1	122.13 (18)	C1—C6—H6	119.8
O2—N3—C8	118.63 (18)	N2—C7—N1	118.39 (19)
O1—N3—C8	119.25 (18)	N2—C7—C8	119.10 (18)
C2—C1—C6	120.08 (19)	N1—C7—C8	122.50 (18)
C2—C1—N1	124.51 (19)	C9—C8—C7	120.17 (19)
C6—C1—N1	115.33 (18)	C9—C8—N3	116.86 (19)
C3—C2—C1	117.52 (19)	C7—C8—N3	122.97 (18)
C3—C2—H2	121.2	C10—C9—C8	119.4 (2)
C1—C2—H2	121.2	C10—C9—H9	120.3
C4—C3—C2	123.5 (2)	C8—C9—H9	120.3
C4—C3—Cl1	118.72 (17)	C9—C10—C11	117.50 (19)
C2—C3—Cl1	117.73 (16)	C9—C10—H10	121.3
C3—C4—C5	117.9 (2)	C11—C10—H10	121.3
C3—C4—H4	121.1	N2—C11—C10	124.77 (18)
C5—C4—H4	121.1	N2—C11—H11	117.6
C6—C5—C4	120.5 (2)	C10—C11—H11	117.6
C7—N1—C1—C2	−19.5 (4)	C1—N1—C7—C8	174.6 (2)
C7—N1—C1—C6	163.8 (2)	N2—C7—C8—C9	0.4 (3)
C6—C1—C2—C3	0.2 (3)	N1—C7—C8—C9	179.9 (2)
N1—C1—C2—C3	−176.37 (19)	N2—C7—C8—N3	−179.92 (19)
C1—C2—C3—C4	−0.1 (3)	N1—C7—C8—N3	−0.5 (3)
C1—C2—C3—Cl1	179.50 (15)	O2—N3—C8—C9	7.4 (3)
C2—C3—C4—C5	−0.2 (3)	O1—N3—C8—C9	−172.91 (19)
Cl1—C3—C4—C5	−179.74 (16)	O2—N3—C8—C7	−172.3 (2)
C3—C4—C5—C6	0.3 (3)	O1—N3—C8—C7	7.4 (3)
C4—C5—C6—C1	−0.1 (3)	C7—C8—C9—C10	−0.1 (3)
C2—C1—C6—C5	−0.1 (3)	N3—C8—C9—C10	−179.82 (18)
N1—C1—C6—C5	176.77 (19)	C8—C9—C10—C11	−0.6 (3)
C11—N2—C7—N1	−179.43 (18)	C7—N2—C11—C10	−0.8 (3)
C11—N2—C7—C8	0.0 (3)	C9—C10—C11—N2	1.1 (3)
C1—N1—C7—N2	−5.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1	0.88 (3)	1.94 (3)	2.647 (2)	137 (2)
C9—H9···Cl1i	0.95	2.79	3.665 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1	0.88 (3)	1.94 (3)	2.647 (2)	137 (2)
C9—H9⋯Cl1i	0.95	2.79	3.665 (2)	153

Symmetry code: (i) .