7-Chloro-5-methyl-2-phenyl-pyrazolo-[1,5-a]pyrimidine.

The fused pyrazole and pyrimidine rings in the title compound, C13H10ClN3, are almost coplanar, their planes being inclined to one another by 0.8 (2)°. The mean plane of the fused ring system is nearly coplanar with the phenyl ring, as indicated by the dihedral angle between their planes of 9.06 (7)°.

Related literature

For pharmacological and biochemical properties of pyra­zolo­[1,5-a]pyrimidine derivatives, see: Selleri et al. (2005 ▶); Almansa et al. (2001 ▶); Suzuki et al. (2001 ▶), Chen et al. (2004 ▶). For related structures, see: Senga et al. (1981 ▶).

Experimental

Crystal data

C13H10ClN3

M = 243.69

Monoclinic,

a = 6.5993 (2) Å

b = 12.6166 (4) Å

c = 13.8702 (5) Å

β = 100.131 (2)°

V = 1136.84 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.41 × 0.32 × 0.21 mm

Data collection

Bruker X8 APEXII area-detector diffractometer

16957 measured reflections

2925 independent reflections

2521 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.103

S = 1.06

2925 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009896/rz5056sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009896/rz5056Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009896/rz5056Isup3.cml

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

C13H10ClN3	F(000) = 504
Mr = 243.69	Dx = 1.418 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2925 reflections
a = 6.5993 (2) Å	θ = 3.0–28.7°
b = 12.6166 (4) Å	µ = 0.31 mm−1
c = 13.8702 (5) Å	T = 296 K
β = 100.131 (2)°	Block, colourless
V = 1136.84 (6) Å3	0.41 × 0.32 × 0.21 mm
Z = 4

Bruker X8 APEXII area-detector diffractometer	2521 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 28.7°, θmin = 3.0°
φ and ω scans	h = −6→8
16957 measured reflections	k = −17→17
2925 independent reflections	l = −18→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0523P)2 + 0.2738P] where P = (Fo2 + 2Fc2)/3
2925 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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
C1	0.07651 (19)	0.69856 (10)	0.25074 (9)	0.0344 (3)
C2	−0.0283 (2)	0.72024 (10)	0.32394 (10)	0.0393 (3)
H2	−0.1459	0.7622	0.3121	0.047*
C3	0.0426 (2)	0.67836 (11)	0.41889 (10)	0.0420 (3)
C4	0.3143 (2)	0.59912 (10)	0.36620 (9)	0.0369 (3)
C5	0.4894 (2)	0.54075 (11)	0.36126 (9)	0.0398 (3)
H5	0.5708	0.5041	0.4120	0.048*
C6	0.51851 (19)	0.54836 (10)	0.26417 (9)	0.0349 (3)
C7	0.68242 (19)	0.49912 (10)	0.21982 (9)	0.0353 (3)
C8	0.8475 (2)	0.44870 (11)	0.27861 (11)	0.0423 (3)
H8	0.8546	0.4468	0.3462	0.051*
C9	1.0010 (2)	0.40136 (12)	0.23699 (13)	0.0502 (4)
H9	1.1112	0.3684	0.2768	0.060*
C10	0.9911 (2)	0.40282 (13)	0.13685 (13)	0.0522 (4)
H10	1.0940	0.3706	0.1092	0.063*
C11	0.8287 (2)	0.45210 (13)	0.07785 (12)	0.0521 (4)
H11	0.8215	0.4528	0.0103	0.063*
C12	0.6755 (2)	0.50072 (12)	0.11910 (11)	0.0448 (3)
H12	0.5671	0.5347	0.0789	0.054*
C13	−0.0778 (3)	0.69939 (16)	0.49944 (12)	0.0599 (4)
H13A	−0.1946	0.7430	0.4748	0.090*
H13B	0.0084	0.7352	0.5525	0.090*
H13C	−0.1239	0.6334	0.5224	0.090*
N1	0.24981 (16)	0.63830 (8)	0.27118 (7)	0.0332 (2)
N2	0.37353 (16)	0.60790 (9)	0.20808 (8)	0.0357 (2)
N3	0.20986 (19)	0.61941 (10)	0.43971 (8)	0.0432 (3)
Cl1	0.00409 (5)	0.74223 (3)	0.13336 (2)	0.04662 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0348 (6)	0.0302 (5)	0.0367 (6)	0.0020 (5)	0.0021 (5)	0.0041 (5)
C2	0.0389 (7)	0.0361 (6)	0.0427 (7)	0.0089 (5)	0.0061 (5)	0.0022 (5)
C3	0.0462 (7)	0.0413 (7)	0.0385 (6)	0.0091 (6)	0.0078 (5)	−0.0005 (5)
C4	0.0393 (6)	0.0370 (6)	0.0326 (6)	0.0047 (5)	0.0014 (5)	0.0011 (5)
C5	0.0401 (7)	0.0423 (7)	0.0351 (6)	0.0103 (5)	0.0012 (5)	0.0014 (5)
C6	0.0331 (6)	0.0323 (6)	0.0382 (6)	0.0011 (5)	0.0029 (5)	−0.0004 (5)
C7	0.0318 (6)	0.0319 (6)	0.0421 (6)	−0.0016 (5)	0.0061 (5)	−0.0006 (5)
C8	0.0379 (7)	0.0412 (7)	0.0459 (7)	0.0033 (5)	0.0021 (5)	−0.0029 (5)
C9	0.0359 (7)	0.0483 (8)	0.0647 (10)	0.0074 (6)	0.0044 (6)	−0.0021 (7)
C10	0.0412 (8)	0.0508 (8)	0.0691 (10)	0.0031 (6)	0.0219 (7)	−0.0026 (7)
C11	0.0527 (8)	0.0576 (9)	0.0508 (8)	0.0019 (7)	0.0224 (7)	0.0033 (7)
C12	0.0414 (7)	0.0502 (8)	0.0436 (7)	0.0053 (6)	0.0095 (6)	0.0043 (6)
C13	0.0659 (10)	0.0735 (11)	0.0433 (8)	0.0281 (9)	0.0176 (7)	0.0038 (7)
N1	0.0334 (5)	0.0318 (5)	0.0338 (5)	0.0036 (4)	0.0042 (4)	0.0023 (4)
N2	0.0344 (5)	0.0360 (5)	0.0368 (5)	0.0026 (4)	0.0068 (4)	0.0024 (4)
N3	0.0479 (6)	0.0474 (6)	0.0335 (5)	0.0130 (5)	0.0053 (5)	0.0004 (5)
Cl1	0.0463 (2)	0.0521 (2)	0.04017 (19)	0.00949 (14)	0.00399 (14)	0.01307 (13)

C1—C2	1.3533 (18)	C7—C8	1.3940 (18)
C1—N1	1.3610 (16)	C8—C9	1.386 (2)
C1—Cl1	1.7055 (13)	C8—H8	0.9300
C2—C3	1.4197 (19)	C9—C10	1.379 (2)
C2—H2	0.9300	C9—H9	0.9300
C3—N3	1.3201 (18)	C10—C11	1.377 (2)
C3—C13	1.504 (2)	C10—H10	0.9300
C4—N3	1.3519 (17)	C11—C12	1.389 (2)
C4—C5	1.3818 (18)	C11—H11	0.9300
C4—N1	1.4019 (16)	C12—H12	0.9300
C5—C6	1.3966 (18)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C6—N2	1.3503 (16)	C13—H13C	0.9600
C6—C7	1.4727 (17)	N1—N2	1.3532 (15)
C7—C12	1.3897 (19)
C2—C1—N1	118.58 (11)	C10—C9—C8	120.34 (14)
C2—C1—Cl1	123.81 (10)	C10—C9—H9	119.8
N1—C1—Cl1	117.61 (9)	C8—C9—H9	119.8
C1—C2—C3	119.48 (12)	C11—C10—C9	119.88 (14)
C1—C2—H2	120.3	C11—C10—H10	120.1
C3—C2—H2	120.3	C9—C10—H10	120.1
N3—C3—C2	122.62 (12)	C10—C11—C12	120.10 (15)
N3—C3—C13	117.87 (12)	C10—C11—H11	119.9
C2—C3—C13	119.50 (13)	C12—C11—H11	119.9
N3—C4—C5	132.85 (12)	C11—C12—C7	120.65 (14)
N3—C4—N1	122.10 (11)	C11—C12—H12	119.7
C5—C4—N1	105.05 (11)	C7—C12—H12	119.7
C4—C5—C6	105.62 (11)	C3—C13—H13A	109.5
C4—C5—H5	127.2	C3—C13—H13B	109.5
C6—C5—H5	127.2	H13A—C13—H13B	109.5
N2—C6—C5	112.96 (11)	C3—C13—H13C	109.5
N2—C6—C7	119.48 (11)	H13A—C13—H13C	109.5
C5—C6—C7	127.56 (11)	H13B—C13—H13C	109.5
C12—C7—C8	118.62 (12)	N2—N1—C1	127.17 (10)
C12—C7—C6	121.13 (12)	N2—N1—C4	112.96 (10)
C8—C7—C6	120.25 (12)	C1—N1—C4	119.86 (11)
C9—C8—C7	120.39 (14)	C6—N2—N1	103.41 (10)
C9—C8—H8	119.8	C3—N3—C4	117.35 (11)
C7—C8—H8	119.8