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

Qing, X.-Y.; Huang, Y.-C.; Yang, L.-L.; Xie, Y.-M.

doi:10.1107/S1600536811018083

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1480

doi:10.1107/S1600536811018083

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

Xiao-Yu Qing,^a Yun-Chuang Huang,^a Ling-Ling Yang ^b and Yong-Mei Xie ^a ^*

^aState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China, and ^bDepartment of Applied Chemistry, College of Chemical Engineering, Sichuan University, Chengdu 610041, People's Republic of China
^*Correspondence e-mail: xieym@scu.edu.cn

(Received 23 February 2011; accepted 12 May 2011; online 20 May 2011)

There are two molecules in the asymmetric unit molecule of the title compound, C₈H₁₀ClN₃O₂. Intramolecular N—H⋯O hydrogen bonds stabilize the molecular structure. There are no classical intermolecular 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_r = 215.64
Triclinic, $[P \overline 1]$
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 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) 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[F² > 2σ(F²)] = 0.061
wR(F²) = 0.149
S = 1.07
4073 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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.

Supporting information

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

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

checkCIF report

Comment top

6–Chloro–N–isopropyl–3–nitropyridin–2–amine derivatives are of great importance owing to their anticancer activity (Lan et al., 2010; Bavetsias et al., 2010). The title compound is one of the key intermediates in our synthetic investigations of anticancer drugs. Now we synthesized the title compound and report here its molecular and crystal structures. In the title compound, C₈H₁₀ClN₃O₂, (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). In crystal, there are two molecules of the compound observed in the asymmetric unit. The intramolecular hydrogen bond N2—H2···O2 (N2···O2 = 2.660Å) stabilizes the almost coplanar arrangement of the N2—C5—C4—N3—O2 plane and pyridine ring. And there are no classical hydrogen bonds observed in the crystall packing (Fig. 2).

Related literature top

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 top

A solution of 0.58 g (3.0 mmol) of 2,6–dichloro–3–nitropyridine in 20 ml of dichloromethane was stirred in the ice–water bath for a few minutes, then 0.38 ml (4.5 mmol) isopropylamine was added dropwise. The reaction was stirred in the ice–water bath for 4 h, concentrated under reduced pressure and purified by silica gel column chromatography. Crystals suitable for X–ray analysis were obtained by slow evaporation from a solution of dichloromethane.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis PRO (Oxford Diffraction, 2006); 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 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Intramolecular hydrogen bonds are presented by blue lines.
	Fig. 2. A packing diagram of the title compound.

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

Crystal data top

C₈H₁₀ClN₃O₂	Z = 4
M_r = 215.64	F(000) = 448
Triclinic, P1	D_x = 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

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	4073 independent reflections
Radiation source: fine-focus sealed tube	2773 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 16.0874 pixels mm^-1	θ_max = 26.4°, θ_min = 3.0°
ω scans	h = −9→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −11→11
T_min = 0.971, T_max = 1.0	l = −19→19
8239 measured reflections

Refinement top

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(F_o²) + (0.0511P)² + 0.4285P] where P = (F_o² + 2F_c²)/3
4073 reflections	(Δ/σ)_max < 0.001
257 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₈H₁₀ClN₃O₂	γ = 78.860 (9)°
M_r = 215.64	V = 1005.16 (19) Å³
Triclinic, P1	Z = 4
a = 7.4283 (8) Å	Mo Kα radiation
b = 8.9573 (10) Å	µ = 0.36 mm⁻¹
c = 15.4301 (17) Å	T = 295 K
α = 89.672 (9)°	0.28 × 0.23 × 0.18 mm
β = 86.252 (9)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	4073 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	2773 reflections with I > 2σ(I)
T_min = 0.971, T_max = 1.0	R_int = 0.022
8239 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.07	Δρ_max = 0.24 e Å⁻³
4073 reflections	Δρ_min = −0.21 e Å⁻³
257 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₈H₁₀ClN₃O₂
M_r	215.64
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.4283 (8), 8.9573 (10), 15.4301 (17)
α, β, γ (°)	89.672 (9), 86.252 (9), 78.860 (9)
V (Å³)	1005.16 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.28 × 0.23 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)
T_min, T_max	0.971, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	8239, 4073, 2773
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.149, 1.07
No. of reflections	4073
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21

Computer programs: CrysAlis PRO (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X–ray measurements.

References

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