2-Methyl-3-(1H-pyrazol-3-yl)imidazo[1,2-a]pyrimidine.

In the title compound, C(10)H(9)N(5), the fused 2-methyl-imidazo[1,2-a]pyrimidine ring system is approximately planar [dihedral angle of 1.14 (9)° between the two fused rings] and the 1H-pyrazole ring is rotated by 28.16 (11)° out of that plane. In the crystal, the mol-ecules are linked into linear chains along the [100] direction by classical inter-molecular N-H⋯N hydrogen bonds.

Related literature

For the medical properties of imidazo[1,2-a]pyrimidine derivatives, see: An et al. (2009 ▶); Kim et al. (2011 ▶); Linton et al. (2011 ▶). For related structures, see: Yang et al. (2008 ▶); Anaflous et al. (2004 ▶).

Experimental

Crystal data

C10H9N5

M = 199.22

Monoclinic,

a = 8.962 (2) Å

b = 8.851 (2) Å

c = 12.481 (3) Å

β = 101.751 (3)°

V = 969.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.50 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.956, T max = 0.993

5121 measured reflections

1907 independent reflections

1552 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.128

S = 1.09

1907 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2000 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812024166/rk2359sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024166/rk2359Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024166/rk2359Isup3.cml

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

C10H9N5	F(000) = 416
Mr = 199.22	Dx = 1.365 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1511 reflections
a = 8.962 (2) Å	θ = 2.6–24.0°
b = 8.851 (2) Å	µ = 0.09 mm−1
c = 12.481 (3) Å	T = 173 K
β = 101.751 (3)°	Bar, pale yellow
V = 969.3 (4) Å3	0.50 × 0.10 × 0.08 mm
Z = 4

Bruker SMART APEX CCD diffractometer	1907 independent reflections
Radiation source: fine-focus sealed tube	1552 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→11
Tmin = 0.956, Tmax = 0.993	k = −10→10
5121 measured reflections	l = −15→8

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.2361P] where P = (Fo2 + 2Fc2)/3
1907 reflections	(Δ/σ)max < 0.001
152 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.14 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
N4	0.44313 (15)	0.15343 (16)	0.08173 (12)	0.0371 (4)
N1	0.65249 (16)	0.11695 (18)	0.21150 (13)	0.0455 (4)
N6	0.68599 (17)	0.2102 (2)	0.03899 (14)	0.0495 (4)
C3	0.39442 (19)	0.0960 (2)	0.17190 (15)	0.0376 (4)
N12	−0.00496 (19)	0.0927 (2)	0.13228 (16)	0.0531 (5)
C5	0.60176 (19)	0.1626 (2)	0.11018 (15)	0.0401 (4)
C9	0.3688 (2)	0.1977 (2)	−0.01970 (16)	0.0475 (5)
H9A	0.2609	0.1930	−0.0399	0.057*
C10	0.23463 (19)	0.0676 (2)	0.17285 (15)	0.0399 (4)
N11	0.12533 (17)	0.14869 (19)	0.10998 (14)	0.0492 (5)
C2	0.5255 (2)	0.0765 (2)	0.24983 (15)	0.0431 (5)
C13	0.0186 (2)	−0.0174 (2)	0.2049 (2)	0.0565 (6)
H13A	−0.0573	−0.0719	0.2319	0.068*
C8	0.4521 (2)	0.2482 (3)	−0.09045 (17)	0.0560 (6)
H8A	0.4038	0.2812	−0.1615	0.067*
C14	0.1724 (2)	−0.0382 (2)	0.23391 (19)	0.0536 (5)
H14A	0.2255	−0.1094	0.2847	0.064*
C7	0.6118 (2)	0.2516 (3)	−0.05784 (18)	0.0560 (6)
H7A	0.6692	0.2859	−0.1092	0.067*
C15	0.5385 (3)	0.0238 (4)	0.3649 (2)	0.0648 (7)
H30A	−0.095 (3)	0.129 (3)	0.1009 (18)	0.061 (7)*
H15C	0.478 (4)	−0.057 (4)	0.372 (3)	0.130 (13)*
H15B	0.639 (4)	−0.005 (4)	0.396 (3)	0.119 (12)*
H15A	0.512 (5)	0.106 (6)	0.410 (4)	0.184 (19)*

	U11	U22	U33	U12	U13	U23
N4	0.0254 (7)	0.0391 (8)	0.0440 (9)	0.0020 (6)	0.0003 (6)	−0.0010 (6)
N1	0.0289 (8)	0.0517 (10)	0.0521 (10)	−0.0001 (7)	−0.0008 (7)	0.0043 (7)
N6	0.0318 (9)	0.0591 (10)	0.0575 (11)	−0.0004 (7)	0.0089 (7)	0.0040 (8)
C3	0.0303 (9)	0.0368 (9)	0.0446 (10)	0.0011 (7)	0.0051 (7)	−0.0007 (8)
N12	0.0259 (9)	0.0593 (11)	0.0735 (12)	0.0001 (7)	0.0086 (8)	0.0012 (9)
C5	0.0259 (9)	0.0429 (10)	0.0492 (11)	0.0010 (7)	0.0026 (7)	−0.0013 (8)
C9	0.0325 (10)	0.0550 (12)	0.0504 (11)	0.0036 (8)	−0.0024 (8)	0.0025 (9)
C10	0.0305 (9)	0.0376 (10)	0.0506 (11)	0.0012 (7)	0.0060 (8)	−0.0044 (8)
N11	0.0265 (8)	0.0531 (10)	0.0666 (11)	0.0001 (7)	0.0063 (7)	0.0046 (8)
C2	0.0344 (10)	0.0436 (11)	0.0485 (11)	−0.0003 (8)	0.0019 (8)	0.0015 (8)
C13	0.0412 (11)	0.0518 (12)	0.0803 (16)	−0.0067 (9)	0.0212 (10)	0.0038 (11)
C8	0.0467 (12)	0.0715 (14)	0.0474 (12)	0.0043 (10)	0.0040 (9)	0.0095 (10)
C14	0.0393 (11)	0.0500 (12)	0.0720 (14)	0.0008 (9)	0.0124 (10)	0.0112 (10)
C7	0.0455 (12)	0.0683 (14)	0.0565 (13)	−0.0008 (10)	0.0156 (10)	0.0093 (11)
C15	0.0530 (15)	0.0809 (18)	0.0544 (14)	−0.0088 (13)	−0.0037 (11)	0.0185 (13)

N4—C9	1.362 (2)	C9—H9A	0.9500
N4—C3	1.384 (2)	C10—N11	1.333 (2)
N4—C5	1.396 (2)	C10—C14	1.394 (3)
N1—C5	1.317 (2)	C2—C15	1.492 (3)
N1—C2	1.369 (2)	C13—C14	1.364 (3)
N6—C7	1.307 (3)	C13—H13A	0.9500
N6—C5	1.345 (2)	C8—C7	1.406 (3)
C3—C2	1.375 (2)	C8—H8A	0.9500
C3—C10	1.456 (2)	C14—H14A	0.9500
N12—C13	1.318 (3)	C7—H7A	0.9500
N12—N11	1.349 (2)	C15—H15C	0.92 (4)
N12—H30A	0.89 (2)	C15—H15B	0.94 (4)
C9—C8	1.343 (3)	C15—H15A	0.98 (5)
C9—N4—C3	133.30 (15)	N1—C2—C3	111.79 (17)
C9—N4—C5	119.96 (16)	N1—C2—C15	120.70 (18)
C3—N4—C5	106.74 (14)	C3—C2—C15	127.5 (2)
C5—N1—C2	105.47 (14)	N12—C13—C14	107.10 (18)
C7—N6—C5	116.74 (17)	N12—C13—H13A	126.4
C2—C3—N4	104.82 (16)	C14—C13—H13A	126.4
C2—C3—C10	132.26 (18)	C9—C8—C7	119.0 (2)
N4—C3—C10	122.92 (15)	C9—C8—H8A	120.5
C13—N12—N11	112.94 (17)	C7—C8—H8A	120.5
C13—N12—H30A	125.4 (15)	C13—C14—C10	105.02 (19)
N11—N12—H30A	121.7 (15)	C13—C14—H14A	127.5
N1—C5—N6	126.85 (16)	C10—C14—H14A	127.5
N1—C5—N4	111.16 (16)	N6—C7—C8	123.9 (2)
N6—C5—N4	121.98 (17)	N6—C7—H7A	118.0
C8—C9—N4	118.35 (17)	C8—C7—H7A	118.0
C8—C9—H9A	120.8	C2—C15—H15C	114 (2)
N4—C9—H9A	120.8	C2—C15—H15B	111 (2)
N11—C10—C14	110.84 (17)	H15C—C15—H15B	106 (3)
N11—C10—C3	120.54 (17)	C2—C15—H15A	110 (3)
C14—C10—C3	128.62 (17)	H15C—C15—H15A	108 (3)
C10—N11—N12	104.10 (16)	H15B—C15—H15A	107 (3)
C9—N4—C3—C2	−178.99 (18)	N4—C3—C10—C14	152.1 (2)
C5—N4—C3—C2	1.06 (19)	C14—C10—N11—N12	0.0 (2)
C9—N4—C3—C10	1.0 (3)	C3—C10—N11—N12	−179.70 (16)
C5—N4—C3—C10	−178.91 (16)	C13—N12—N11—C10	0.0 (2)
C2—N1—C5—N6	−178.49 (18)	C5—N1—C2—C3	0.3 (2)
C2—N1—C5—N4	0.4 (2)	C5—N1—C2—C15	−177.7 (2)
C7—N6—C5—N1	−179.55 (19)	N4—C3—C2—N1	−0.9 (2)
C7—N6—C5—N4	1.7 (3)	C10—C3—C2—N1	179.06 (18)
C9—N4—C5—N1	179.12 (16)	N4—C3—C2—C15	177.0 (2)
C3—N4—C5—N1	−0.9 (2)	C10—C3—C2—C15	−3.0 (4)
C9—N4—C5—N6	−2.0 (3)	N11—N12—C13—C14	−0.1 (3)
C3—N4—C5—N6	177.99 (17)	N4—C9—C8—C7	0.8 (3)
C3—N4—C9—C8	−179.3 (2)	N12—C13—C14—C10	0.0 (3)
C5—N4—C9—C8	0.6 (3)	N11—C10—C14—C13	0.0 (2)
C2—C3—C10—N11	151.8 (2)	C3—C10—C14—C13	179.63 (19)
N4—C3—C10—N11	−28.2 (3)	C5—N6—C7—C8	−0.2 (3)
C2—C3—C10—C14	−27.8 (3)	C9—C8—C7—N6	−1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N12—H30A···N6i	0.89 (2)	2.08 (2)	2.966 (2)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N12—H30A⋯N6i	0.89 (2)	2.08 (2)	2.966 (2)	175 (2)

Symmetry code: (i) .