4-Chloro-6-meth-oxy-pyrimidin-2-amine.

The title compound, C5H6ClN3O, is essentially planar with a maximum deviation of 0.0256 (11) Å for all non-H atoms. In the crystal, adjacent mol-ecules are linked by a pair of N-H⋯N hydrogen bonds, forming an inversion dimer with an R2(2)(8) ring motif. The dimers are further linked via N-H⋯O hydrogen bonds into an undulating sheet structure parallel to the bc plane.

Related literature

For the biological activity of pyrimidine and amino­pyrimidine derivatives, see: Hunt et al. (1980 ▶); Baker & Santi (1965 ▶). For related structures, see: Schwalbe & Williams (1982 ▶); Hu et al. (2002 ▶); Chinnakali et al. (1999 ▶); Skovsgaard & Bond (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C5H6ClN3O

M = 159.58

Monoclinic,

a = 3.7683 (2) Å

b = 16.4455 (2) Å

c = 10.7867 (2) Å

β = 94.550 (1)°

V = 666.36 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.50 mm−1

T = 100 K

0.49 × 0.28 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.791, T max = 0.904

9524 measured reflections

2436 independent reflections

2266 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.070

S = 1.06

2436 reflections

100 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681204528X/is5214sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204528X/is5214Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204528X/is5214Isup3.cml

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

C5H6ClN3O	F(000) = 328
Mr = 159.58	Dx = 1.591 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6060 reflections
a = 3.7683 (2) Å	θ = 3.8–32.6°
b = 16.4455 (2) Å	µ = 0.50 mm−1
c = 10.7867 (2) Å	T = 100 K
β = 94.550 (1)°	Block, colourless
V = 666.36 (4) Å3	0.49 × 0.28 × 0.21 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2436 independent reflections
Radiation source: fine-focus sealed tube	2266 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 32.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→5
Tmin = 0.791, Tmax = 0.904	k = −24→21
9524 measured reflections	l = −16→14

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0306P)2 + 0.3355P] where P = (Fo2 + 2Fc2)/3
2436 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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	1.11362 (6)	0.546310 (13)	0.64838 (2)	0.01425 (6)
O1	0.57563 (19)	0.80520 (4)	0.79576 (6)	0.01449 (13)
N1	0.9448 (2)	0.57688 (5)	0.87272 (7)	0.01299 (14)
N2	0.6906 (2)	0.70257 (5)	0.93883 (7)	0.01284 (14)
N3	0.8057 (3)	0.59594 (5)	1.07440 (8)	0.01996 (17)
C1	0.8338 (2)	0.68624 (5)	0.72638 (8)	0.01284 (15)
H1A	0.8437	0.7075	0.6448	0.015*
C2	0.9490 (2)	0.60954 (5)	0.76040 (8)	0.01137 (14)
C3	0.8137 (2)	0.62570 (5)	0.95924 (8)	0.01305 (15)
C4	0.7000 (2)	0.73004 (5)	0.82415 (8)	0.01155 (15)
C5	0.4336 (3)	0.85141 (6)	0.89378 (9)	0.01568 (16)
H5A	0.3073	0.8992	0.8583	0.024*
H5B	0.6286	0.8691	0.9532	0.024*
H5C	0.2680	0.8174	0.9366	0.024*
H2N3	0.722 (4)	0.6245 (10)	1.1281 (15)	0.027 (4)*
H1N3	0.876 (4)	0.5475 (10)	1.0891 (15)	0.023 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.01773 (10)	0.01199 (10)	0.01346 (10)	0.00039 (7)	0.00388 (7)	−0.00276 (7)
O1	0.0206 (3)	0.0093 (3)	0.0136 (3)	0.0025 (2)	0.0019 (2)	0.0013 (2)
N1	0.0169 (3)	0.0103 (3)	0.0119 (3)	0.0017 (2)	0.0022 (2)	0.0000 (2)
N2	0.0170 (3)	0.0092 (3)	0.0124 (3)	0.0018 (2)	0.0017 (2)	0.0004 (2)
N3	0.0359 (5)	0.0129 (4)	0.0119 (3)	0.0084 (3)	0.0069 (3)	0.0022 (3)
C1	0.0171 (4)	0.0105 (3)	0.0110 (3)	0.0002 (3)	0.0014 (3)	0.0003 (3)
C2	0.0128 (3)	0.0099 (3)	0.0116 (3)	−0.0006 (3)	0.0018 (3)	−0.0018 (3)
C3	0.0171 (4)	0.0103 (3)	0.0118 (3)	0.0014 (3)	0.0020 (3)	0.0005 (3)
C4	0.0130 (3)	0.0086 (3)	0.0130 (3)	−0.0001 (3)	0.0004 (3)	0.0003 (3)
C5	0.0176 (4)	0.0115 (4)	0.0182 (4)	0.0029 (3)	0.0026 (3)	−0.0013 (3)

Cl1—C2	1.7449 (9)	N3—H2N3	0.828 (16)
O1—C4	1.3485 (10)	N3—H1N3	0.850 (16)
O1—C5	1.4393 (11)	C1—C2	1.3743 (12)
N1—C2	1.3266 (11)	C1—C4	1.4035 (12)
N1—C3	1.3539 (11)	C1—H1A	0.9500
N2—C4	1.3201 (11)	C5—H5A	0.9800
N2—C3	1.3584 (11)	C5—H5B	0.9800
N3—C3	1.3378 (12)	C5—H5C	0.9800
C4—O1—C5	117.38 (7)	N3—C3—N1	117.35 (8)
C2—N1—C3	114.89 (8)	N3—C3—N2	117.28 (8)
C4—N2—C3	115.86 (8)	N1—C3—N2	125.37 (8)
C3—N3—H2N3	118.7 (11)	N2—C4—O1	119.46 (8)
C3—N3—H1N3	119.1 (11)	N2—C4—C1	124.50 (8)
H2N3—N3—H1N3	122.1 (15)	O1—C4—C1	116.04 (8)
C2—C1—C4	113.28 (8)	O1—C5—H5A	109.5
C2—C1—H1A	123.4	O1—C5—H5B	109.5
C4—C1—H1A	123.4	H5A—C5—H5B	109.5
N1—C2—C1	126.09 (8)	O1—C5—H5C	109.5
N1—C2—Cl1	114.95 (6)	H5A—C5—H5C	109.5
C1—C2—Cl1	118.96 (7)	H5B—C5—H5C	109.5
C3—N1—C2—C1	−0.18 (13)	C4—N2—C3—N1	0.61 (14)
C3—N1—C2—Cl1	−179.36 (6)	C3—N2—C4—O1	178.63 (8)
C4—C1—C2—N1	−0.63 (13)	C3—N2—C4—C1	−1.55 (13)
C4—C1—C2—Cl1	178.52 (6)	C5—O1—C4—N2	−0.73 (12)
C2—N1—C3—N3	−179.55 (9)	C5—O1—C4—C1	179.44 (8)
C2—N1—C3—N2	0.22 (13)	C2—C1—C4—N2	1.55 (13)
C4—N2—C3—N3	−179.62 (9)	C2—C1—C4—O1	−178.62 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H2N3···O1i	0.828 (16)	2.251 (17)	3.0699 (11)	170.1 (15)
N3—H1N3···N1ii	0.850 (16)	2.183 (16)	3.0335 (12)	180 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H2N3⋯O1i	0.828 (16)	2.251 (17)	3.0699 (11)	170.1 (15)
N3—H1N3⋯N1ii	0.850 (16)	2.183 (16)	3.0335 (12)	180 (2)

Symmetry codes: (i) ; (ii) .