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

There are two mol-ecules in the asymmetric unit mol-ecule of the title compound, C(8)H(10)ClN(3)O(2). Intra-molecular N-H⋯O hydrogen bonds stabilize the mol-ecular structure. There are no classical inter-molecular hydrogen bonds in the crystal structure.

Related literature

For the biological activity of 6-chloro-N-isopropyl-3-nitro­pyridin-2-amine derivatives, see: Lan et al. (2010 ▶); Bavetsias et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H10ClN3O2

M = 215.64

Triclinic,

a = 7.4283 (8) Å

b = 8.9573 (10) Å

c = 15.4301 (17) Å

α = 89.672 (9)°

β = 86.252 (9)°

γ = 78.860 (9)°

V = 1005.16 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 295 K

0.28 × 0.23 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.971, T max = 1.0

8239 measured reflections

4073 independent reflections

2773 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.149

S = 1.07

4073 reflections

257 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); 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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018083/rk2268sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018083/rk2268Isup2.hkl

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

C8H10ClN3O2	Z = 4
Mr = 215.64	F(000) = 448
Triclinic, P1	Dx = 1.425 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 7.4283 (8) Å	Cell parameters from 2782 reflections
b = 8.9573 (10) Å	θ = 3.0–29.2°
c = 15.4301 (17) Å	µ = 0.36 mm−1
α = 89.672 (9)°	T = 295 K
β = 86.252 (9)°	Block, colourless
γ = 78.860 (9)°	0.28 × 0.23 × 0.18 mm
V = 1005.16 (19) Å3

Oxford Diffraction Xcalibur Eos diffractometer	4073 independent reflections
Radiation source: fine-focus sealed tube	2773 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.0°
ω scans	h = −9→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −11→11
Tmin = 0.971, Tmax = 1.0	l = −19→19
8239 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.4285P] where P = (Fo2 + 2Fc2)/3
4073 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.21 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	0.27337 (14)	−0.24866 (9)	0.55983 (6)	0.0755 (3)
Cl2	0.22248 (13)	0.27284 (9)	0.95299 (6)	0.0649 (3)
O1	0.2452 (5)	0.3317 (3)	0.30153 (16)	0.1036 (10)
O2	0.2403 (4)	0.4488 (3)	0.42175 (16)	0.0911 (9)
O3	0.3152 (4)	0.9485 (3)	1.08072 (16)	0.0773 (7)
O4	0.3156 (4)	0.8329 (3)	1.20304 (15)	0.0806 (8)
N1	0.2670 (3)	0.0404 (3)	0.55475 (14)	0.0438 (6)
N2	0.2640 (4)	0.2945 (3)	0.56967 (15)	0.0510 (6)
H2	0.2646	0.3818	0.5464	0.061*
N3	0.2445 (4)	0.3306 (4)	0.38070 (18)	0.0692 (8)
N4	0.2595 (3)	0.5533 (2)	0.95342 (14)	0.0420 (5)
N5	0.2928 (4)	0.8005 (3)	0.93459 (15)	0.0504 (6)
H5	0.3087	0.8849	0.9562	0.060*
N6	0.3082 (4)	0.8333 (3)	1.12380 (17)	0.0573 (7)
C1	0.2645 (4)	−0.0767 (3)	0.5049 (2)	0.0476 (7)
C2	0.2568 (4)	−0.0768 (4)	0.4162 (2)	0.0576 (8)
H2A	0.2560	−0.1652	0.3850	0.069*
C3	0.2504 (4)	0.0606 (4)	0.3764 (2)	0.0563 (8)
H3	0.2456	0.0676	0.3164	0.068*
C4	0.2512 (4)	0.1893 (3)	0.42550 (18)	0.0487 (7)
C5	0.2595 (4)	0.1783 (3)	0.51714 (17)	0.0421 (6)
C6	0.2678 (4)	0.2846 (3)	0.66435 (17)	0.0452 (7)
H6	0.3556	0.1926	0.6783	0.054*
C7	0.0831 (4)	0.2722 (4)	0.7059 (2)	0.0684 (9)
H7B	−0.0062	0.3597	0.6912	0.103*
H7C	0.0894	0.2673	0.7679	0.103*
H7A	0.0479	0.1818	0.6853	0.103*
C8	0.3374 (6)	0.4205 (4)	0.6968 (2)	0.0769 (11)
H8A	0.4551	0.4237	0.6680	0.115*
H8C	0.3493	0.4121	0.7583	0.115*
H8B	0.2520	0.5120	0.6847	0.115*
C9	0.2499 (4)	0.4388 (3)	1.00420 (19)	0.0439 (7)
C10	0.2613 (4)	0.4363 (3)	1.0939 (2)	0.0503 (7)
H10	0.2556	0.3494	1.1264	0.060*
C11	0.2814 (4)	0.5690 (4)	1.13095 (19)	0.0493 (7)
H11	0.2892	0.5746	1.1907	0.059*
C12	0.2901 (4)	0.6956 (3)	1.08053 (18)	0.0428 (6)
C13	0.2804 (4)	0.6865 (3)	0.98920 (18)	0.0405 (6)
C14	0.2811 (4)	0.7920 (3)	0.84014 (18)	0.0481 (7)
H14	0.3504	0.6925	0.8201	0.058*
C15	0.0870 (5)	0.8048 (6)	0.8159 (2)	0.0928 (14)
H15C	0.0166	0.9022	0.8341	0.139*
H15B	0.0344	0.7258	0.8439	0.139*
H15A	0.0854	0.7946	0.7540	0.139*
C16	0.3737 (5)	0.9121 (4)	0.7985 (2)	0.0737 (10)
H16A	0.3745	0.9037	0.7365	0.111*
H16B	0.4978	0.8982	0.8156	0.111*
H16C	0.3078	1.0110	0.8169	0.111*

	U11	U22	U33	U12	U13	U23
Cl1	0.1077 (7)	0.0471 (5)	0.0766 (7)	−0.0291 (5)	0.0014 (5)	−0.0021 (4)
Cl2	0.0873 (6)	0.0453 (5)	0.0662 (6)	−0.0228 (4)	−0.0058 (4)	0.0016 (4)
O1	0.177 (3)	0.092 (2)	0.0360 (15)	−0.0075 (19)	−0.0197 (17)	0.0146 (14)
O2	0.164 (3)	0.0536 (15)	0.0507 (16)	−0.0076 (16)	−0.0119 (16)	0.0113 (13)
O3	0.128 (2)	0.0505 (14)	0.0553 (15)	−0.0203 (14)	−0.0114 (14)	−0.0059 (12)
O4	0.118 (2)	0.0906 (19)	0.0381 (14)	−0.0327 (15)	−0.0006 (13)	−0.0173 (13)
N1	0.0527 (14)	0.0420 (13)	0.0369 (13)	−0.0108 (10)	−0.0001 (11)	−0.0027 (11)
N2	0.0850 (18)	0.0355 (12)	0.0317 (13)	−0.0100 (12)	−0.0043 (12)	0.0031 (10)
N3	0.096 (2)	0.0656 (19)	0.0395 (17)	0.0025 (16)	−0.0126 (15)	0.0071 (15)
N4	0.0463 (13)	0.0424 (13)	0.0370 (13)	−0.0089 (10)	−0.0009 (10)	0.0026 (11)
N5	0.0793 (18)	0.0376 (13)	0.0359 (13)	−0.0146 (12)	−0.0054 (12)	−0.0011 (11)
N6	0.0691 (18)	0.0601 (17)	0.0418 (16)	−0.0106 (13)	−0.0013 (13)	−0.0112 (14)
C1	0.0488 (17)	0.0441 (16)	0.0514 (19)	−0.0130 (13)	−0.0023 (13)	−0.0034 (14)
C2	0.061 (2)	0.061 (2)	0.051 (2)	−0.0123 (15)	−0.0064 (15)	−0.0181 (17)
C3	0.059 (2)	0.071 (2)	0.0363 (17)	−0.0060 (16)	−0.0079 (14)	−0.0083 (16)
C4	0.0536 (18)	0.0546 (18)	0.0356 (16)	−0.0038 (14)	−0.0066 (13)	0.0015 (14)
C5	0.0476 (16)	0.0429 (16)	0.0344 (15)	−0.0051 (12)	−0.0022 (12)	−0.0028 (12)
C6	0.0665 (19)	0.0372 (15)	0.0311 (15)	−0.0067 (13)	−0.0063 (13)	−0.0017 (12)
C7	0.069 (2)	0.083 (2)	0.049 (2)	−0.0039 (18)	0.0027 (17)	0.0019 (18)
C8	0.129 (3)	0.054 (2)	0.053 (2)	−0.028 (2)	−0.016 (2)	−0.0034 (17)
C9	0.0434 (16)	0.0430 (16)	0.0451 (17)	−0.0083 (12)	−0.0017 (13)	0.0028 (13)
C10	0.0507 (18)	0.0546 (18)	0.0471 (18)	−0.0143 (14)	−0.0029 (14)	0.0154 (15)
C11	0.0485 (17)	0.067 (2)	0.0323 (16)	−0.0125 (14)	0.0005 (12)	0.0043 (14)
C12	0.0435 (16)	0.0474 (16)	0.0367 (16)	−0.0073 (12)	−0.0008 (12)	−0.0055 (13)
C13	0.0426 (15)	0.0404 (15)	0.0367 (15)	−0.0037 (11)	−0.0007 (12)	0.0014 (12)
C14	0.0665 (19)	0.0433 (16)	0.0363 (16)	−0.0139 (14)	−0.0075 (14)	0.0038 (13)
C15	0.072 (3)	0.149 (4)	0.059 (2)	−0.024 (3)	−0.011 (2)	0.024 (3)
C16	0.110 (3)	0.068 (2)	0.051 (2)	−0.036 (2)	−0.005 (2)	0.0099 (18)

Cl1—C1	1.746 (3)	C6—H6	0.9800
Cl2—C9	1.740 (3)	C6—C7	1.500 (4)
O1—N3	1.221 (3)	C6—C8	1.511 (4)
O2—N3	1.231 (3)	C7—H7B	0.9600
O3—N6	1.232 (3)	C7—H7C	0.9600
O4—N6	1.228 (3)	C7—H7A	0.9600
N1—C1	1.308 (3)	C8—H8A	0.9600
N1—C5	1.355 (3)	C8—H8C	0.9600
N2—H2	0.8600	C8—H8B	0.9600
N2—C5	1.329 (3)	C9—C10	1.392 (4)
N2—C6	1.465 (3)	C10—H10	0.9300
N3—C4	1.432 (4)	C10—C11	1.360 (4)
N4—C9	1.297 (3)	C11—H11	0.9300
N4—C13	1.357 (3)	C11—C12	1.381 (4)
N5—H5	0.8600	C12—C13	1.420 (4)
N5—C13	1.333 (3)	C14—H14	0.9800
N5—C14	1.469 (3)	C14—C15	1.496 (4)
N6—C12	1.438 (4)	C14—C16	1.504 (4)
C1—C2	1.374 (4)	C15—H15C	0.9600
C2—H2A	0.9300	C15—H15B	0.9600
C2—C3	1.365 (4)	C15—H15A	0.9600
C3—H3	0.9300	C16—H16A	0.9600
C3—C4	1.384 (4)	C16—H16B	0.9600
C4—C5	1.421 (4)	C16—H16C	0.9600
O1—N3—O2	120.7 (3)	C6—C8—H8C	109.5
O1—N3—C4	119.2 (3)	C6—C8—H8B	109.5
O2—N3—C4	120.1 (3)	C7—C6—H6	108.1
O3—N6—C12	119.4 (2)	C7—C6—C8	112.7 (3)
O4—N6—O3	121.6 (3)	H7B—C7—H7C	109.5
O4—N6—C12	118.9 (3)	H7B—C7—H7A	109.5
N1—C1—Cl1	114.6 (2)	H7C—C7—H7A	109.5
N1—C1—C2	126.9 (3)	C8—C6—H6	108.1
N1—C5—C4	118.8 (2)	H8A—C8—H8C	109.5
N2—C5—N1	116.6 (2)	H8A—C8—H8B	109.5
N2—C5—C4	124.6 (3)	H8C—C8—H8B	109.5
N2—C6—H6	108.1	C9—N4—C13	118.6 (2)
N2—C6—C7	111.4 (2)	C9—C10—H10	122.1
N2—C6—C8	108.3 (2)	C10—C9—Cl2	118.0 (2)
N4—C9—Cl2	115.5 (2)	C10—C11—H11	119.7
N4—C9—C10	126.5 (3)	C10—C11—C12	120.5 (3)
N4—C13—C12	118.9 (2)	C11—C10—C9	115.7 (3)
N5—C13—N4	116.6 (2)	C11—C10—H10	122.1
N5—C13—C12	124.4 (2)	C11—C12—N6	117.8 (3)
N5—C14—H14	107.9	C11—C12—C13	119.7 (3)
N5—C14—C15	111.9 (3)	C12—C11—H11	119.7
N5—C14—C16	108.4 (2)	C13—N5—H5	117.7
C1—N1—C5	118.3 (2)	C13—N5—C14	124.6 (2)
C1—C2—H2A	122.0	C13—C12—N6	122.5 (3)
C2—C1—Cl1	118.4 (2)	C14—N5—H5	117.7
C2—C3—H3	120.0	C14—C15—H15C	109.5
C2—C3—C4	120.0 (3)	C14—C15—H15B	109.5
C3—C2—C1	116.0 (3)	C14—C15—H15A	109.5
C3—C2—H2A	122.0	C14—C16—H16A	109.5
C3—C4—N3	117.8 (3)	C14—C16—H16B	109.5
C3—C4—C5	120.0 (3)	C14—C16—H16C	109.5
C4—C3—H3	120.0	C15—C14—H14	107.9
C5—N2—H2	117.6	C15—C14—C16	112.8 (3)
C5—N2—C6	124.8 (2)	H15C—C15—H15B	109.5
C5—C4—N3	122.2 (3)	H15C—C15—H15A	109.5
C6—N2—H2	117.6	H15B—C15—H15A	109.5
C6—C7—H7B	109.5	C16—C14—H14	107.9
C6—C7—H7C	109.5	H16A—C16—H16B	109.5
C6—C7—H7A	109.5	H16A—C16—H16C	109.5
C6—C8—H8A	109.5	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	2.02	2.660 (3)	130
N5—H5···O3	0.86	2.01	2.653 (3)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.86	2.02	2.660 (3)	130
N5—H5⋯O3	0.86	2.01	2.653 (3)	130