Ethyl 7-methyl-2-phenyl-pyrazolo-[1,5-a]pyrimidine-5-carboxyl-ate.

The fused pyrazole and pyrimidine rings in the title compound, C16H15N3O2, are almost coplanar, being inclined to one another by 1.31 (12)°. The mean plane of this fused ring system is nearly coplanar with the phenyl ring, as indicated by the dihedral angle between their planes of 1.31 (12)°. The fused-ring system and the phenyl ring are nearly coplanar, as indicated by the dihedral angle of 1.27 (10)°. In the crystal, mol-ecules form inversion dimers via pairs of C-H⋯O hydrogen bonds. C-H⋯N inter-actions connect the dimers into a three-dimensional network. In addition, π-π contacts are observed, with centroid-centroid distances of 3.426 (2) Å.

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: Chimichi et al. (1992 ▶).

Experimental

Crystal data

C16H15N3O2

M = 281.31

Orthorhombic,

a = 8.0542 (8) Å

b = 16.4104 (19) Å

c = 21.635 (2) Å

V = 2859.5 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.41 × 0.32 × 0.21 mm

Data collection

Bruker X8 APEXII area-detector diffractometer

12894 measured reflections

2783 independent reflections

1919 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.170

S = 1.04

2783 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.36 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/S1600536813009902/rz5057sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009902/rz5057Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009902/rz5057Isup3.cml

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

C16H15N3O2	F(000) = 1184
Mr = 281.31	Dx = 1.307 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ac 2ab	Cell parameters from 2783 reflections
a = 8.0542 (8) Å	θ = 2.5–26.0°
b = 16.4104 (19) Å	µ = 0.09 mm−1
c = 21.635 (2) Å	T = 296 K
V = 2859.5 (5) Å3	Block, colourless
Z = 8	0.41 × 0.32 × 0.21 mm

Bruker X8 APEXII area-detector diffractometer	1919 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 26.0°, θmin = 2.5°
φ and ω scans	h = −9→9
12894 measured reflections	k = −20→19
2783 independent reflections	l = −25→26

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)] = 0.052	Hydrogen site location: difference Fourier map
wR(F2) = 0.170	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0849P)2 + 1.249P] where P = (Fo2 + 2Fc2)/3
2783 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.36 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	0.7015 (3)	0.59846 (13)	−0.00919 (11)	0.0423 (5)
C2	0.4533 (2)	0.62909 (13)	0.03355 (10)	0.0392 (5)
C3	0.2988 (3)	0.66217 (13)	0.04562 (11)	0.0431 (5)
H3	0.2464	0.7041	0.0243	0.052*
C4	0.2383 (3)	0.61938 (13)	0.09644 (10)	0.0404 (5)
C5	0.0780 (3)	0.63145 (14)	0.12822 (10)	0.0426 (5)
C6	−0.0290 (3)	0.69261 (15)	0.10875 (12)	0.0531 (6)
H6	0.0002	0.7255	0.0755	0.064*
C7	−0.1796 (3)	0.70489 (17)	0.13873 (14)	0.0660 (8)
H7	−0.2511	0.7456	0.1252	0.079*
C8	−0.2234 (4)	0.65694 (18)	0.18851 (14)	0.0689 (8)
H8	−0.3243	0.6650	0.2085	0.083*
C9	−0.1158 (3)	0.5968 (2)	0.20843 (13)	0.0681 (8)
H9	−0.1438	0.5649	0.2424	0.082*
C10	0.0323 (3)	0.58363 (17)	0.17833 (12)	0.0557 (7)
H10	0.1025	0.5422	0.1917	0.067*
C11	0.6159 (3)	0.52087 (13)	0.07911 (10)	0.0423 (5)
C12	0.7310 (3)	0.53683 (14)	0.03464 (11)	0.0455 (6)
H12	0.8291	0.5070	0.0332	0.055*
C13	0.6281 (3)	0.45638 (16)	0.12736 (12)	0.0584 (7)
H13A	0.5308	0.4578	0.1530	0.088*
H13B	0.7247	0.4658	0.1523	0.088*
H13C	0.6365	0.4040	0.1079	0.088*
C14	0.8285 (3)	0.61382 (15)	−0.05871 (12)	0.0493 (6)
C15	0.8726 (4)	0.6665 (2)	−0.15930 (14)	0.0784 (9)
H15A	0.9632	0.6276	−0.1601	0.094*
H15B	0.9191	0.7208	−0.1558	0.094*
C16	0.7733 (6)	0.6597 (3)	−0.21607 (16)	0.1145 (15)
H16A	0.8427	0.6700	−0.2513	0.172*
H16B	0.6848	0.6989	−0.2150	0.172*
H16C	0.7276	0.6058	−0.2190	0.172*
N1	0.3450 (2)	0.56159 (11)	0.11673 (9)	0.0435 (5)
N2	0.4760 (2)	0.56790 (11)	0.07779 (8)	0.0395 (5)
N3	0.5670 (2)	0.64421 (11)	−0.01033 (9)	0.0424 (5)
O1	0.9709 (2)	0.59496 (15)	−0.05385 (11)	0.0868 (7)
O2	0.76394 (19)	0.65002 (11)	−0.10746 (8)	0.0575 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0374 (11)	0.0394 (12)	0.0500 (14)	−0.0004 (9)	−0.0033 (9)	−0.0011 (11)
C2	0.0402 (11)	0.0342 (11)	0.0432 (13)	−0.0002 (9)	−0.0029 (9)	0.0031 (10)
C3	0.0424 (11)	0.0386 (12)	0.0484 (14)	0.0045 (9)	0.0018 (10)	0.0049 (10)
C4	0.0398 (11)	0.0401 (11)	0.0411 (13)	−0.0031 (9)	−0.0021 (9)	−0.0020 (10)
C5	0.0410 (11)	0.0439 (12)	0.0429 (13)	−0.0096 (9)	0.0017 (9)	−0.0050 (11)
C6	0.0491 (13)	0.0494 (14)	0.0607 (16)	−0.0019 (11)	0.0115 (11)	0.0015 (12)
C7	0.0535 (14)	0.0578 (16)	0.087 (2)	0.0039 (12)	0.0200 (14)	−0.0032 (16)
C8	0.0566 (16)	0.074 (2)	0.076 (2)	−0.0108 (14)	0.0254 (14)	−0.0131 (17)
C9	0.0625 (16)	0.083 (2)	0.0586 (18)	−0.0192 (15)	0.0127 (13)	0.0060 (15)
C10	0.0517 (13)	0.0662 (16)	0.0492 (15)	−0.0084 (12)	−0.0017 (11)	0.0072 (13)
C11	0.0392 (11)	0.0382 (12)	0.0496 (14)	−0.0004 (9)	−0.0137 (9)	0.0017 (11)
C12	0.0359 (10)	0.0436 (13)	0.0570 (15)	0.0039 (9)	−0.0077 (10)	−0.0002 (12)
C13	0.0522 (14)	0.0578 (15)	0.0650 (17)	0.0032 (12)	−0.0134 (12)	0.0171 (13)
C14	0.0387 (12)	0.0475 (13)	0.0618 (16)	0.0016 (10)	0.0021 (10)	−0.0024 (12)
C15	0.0669 (17)	0.101 (2)	0.068 (2)	−0.0081 (17)	0.0267 (15)	0.0040 (18)
C16	0.124 (3)	0.146 (4)	0.073 (3)	0.013 (3)	0.020 (2)	0.028 (3)
N1	0.0415 (9)	0.0463 (11)	0.0428 (11)	−0.0036 (8)	−0.0023 (8)	0.0023 (9)
N2	0.0384 (9)	0.0375 (10)	0.0425 (11)	−0.0020 (7)	−0.0056 (8)	0.0024 (8)
N3	0.0388 (9)	0.0402 (10)	0.0482 (11)	0.0021 (8)	0.0031 (8)	0.0030 (9)
O1	0.0407 (10)	0.1158 (18)	0.1039 (17)	0.0204 (10)	0.0123 (10)	0.0295 (14)
O2	0.0442 (9)	0.0723 (12)	0.0561 (11)	0.0020 (8)	0.0098 (8)	0.0099 (10)

C1—N3	1.318 (3)	C9—H9	0.9300
C1—C12	1.407 (3)	C10—H10	0.9300
C1—C14	1.503 (3)	C11—C12	1.361 (3)
C2—N3	1.342 (3)	C11—N2	1.366 (3)
C2—C3	1.383 (3)	C11—C13	1.490 (3)
C2—N2	1.399 (3)	C12—H12	0.9300
C3—C4	1.393 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—N1	1.353 (3)	C13—H13C	0.9600
C4—C5	1.476 (3)	C14—O1	1.192 (3)
C5—C10	1.388 (3)	C14—O2	1.318 (3)
C5—C6	1.389 (3)	C15—O2	1.448 (3)
C6—C7	1.390 (3)	C15—C16	1.470 (5)
C6—H6	0.9300	C15—H15A	0.9700
C7—C8	1.380 (4)	C15—H15B	0.9700
C7—H7	0.9300	C16—H16A	0.9600
C8—C9	1.382 (4)	C16—H16B	0.9600
C8—H8	0.9300	C16—H16C	0.9600
C9—C10	1.376 (4)	N1—N2	1.354 (2)
N3—C1—C12	124.1 (2)	N2—C11—C13	118.0 (2)
N3—C1—C14	116.8 (2)	C11—C12—C1	120.0 (2)
C12—C1—C14	119.09 (19)	C11—C12—H12	120.0
N3—C2—C3	132.5 (2)	C1—C12—H12	120.0
N3—C2—N2	121.83 (18)	C11—C13—H13A	109.5
C3—C2—N2	105.69 (18)	C11—C13—H13B	109.5
C2—C3—C4	105.43 (19)	H13A—C13—H13B	109.5
C2—C3—H3	127.3	C11—C13—H13C	109.5
C4—C3—H3	127.3	H13A—C13—H13C	109.5
N1—C4—C3	112.77 (19)	H13B—C13—H13C	109.5
N1—C4—C5	119.9 (2)	O1—C14—O2	124.6 (2)
C3—C4—C5	127.3 (2)	O1—C14—C1	123.3 (2)
C10—C5—C6	118.7 (2)	O2—C14—C1	112.16 (18)
C10—C5—C4	121.3 (2)	O2—C15—C16	107.7 (3)
C6—C5—C4	119.9 (2)	O2—C15—H15A	110.2
C5—C6—C7	120.3 (2)	C16—C15—H15A	110.2
C5—C6—H6	119.8	O2—C15—H15B	110.2
C7—C6—H6	119.8	C16—C15—H15B	110.2
C8—C7—C6	120.3 (3)	H15A—C15—H15B	108.5
C8—C7—H7	119.8	C15—C16—H16A	109.5
C6—C7—H7	119.8	C15—C16—H16B	109.5
C7—C8—C9	119.4 (2)	H16A—C16—H16B	109.5
C7—C8—H8	120.3	C15—C16—H16C	109.5
C9—C8—H8	120.3	H16A—C16—H16C	109.5
C10—C9—C8	120.5 (3)	H16B—C16—H16C	109.5
C10—C9—H9	119.7	C4—N1—N2	103.87 (17)
C8—C9—H9	119.7	N1—N2—C11	125.91 (18)
C9—C10—C5	120.7 (3)	N1—N2—C2	112.24 (16)
C9—C10—H10	119.6	C11—N2—C2	121.85 (18)
C5—C10—H10	119.6	C1—N3—C2	116.24 (19)
C12—C11—N2	115.98 (19)	C14—O2—C15	117.8 (2)
C12—C11—C13	126.0 (2)
N3—C2—C3—C4	178.2 (2)	N3—C1—C14—O2	−22.0 (3)
N2—C2—C3—C4	0.3 (2)	C12—C1—C14—O2	157.4 (2)
C2—C3—C4—N1	−0.2 (3)	C3—C4—N1—N2	−0.1 (2)
C2—C3—C4—C5	179.4 (2)	C5—C4—N1—N2	−179.70 (18)
N1—C4—C5—C10	−1.1 (3)	C4—N1—N2—C11	−178.94 (19)
C3—C4—C5—C10	179.3 (2)	C4—N1—N2—C2	0.3 (2)
N1—C4—C5—C6	177.8 (2)	C12—C11—N2—N1	178.77 (19)
C3—C4—C5—C6	−1.8 (3)	C13—C11—N2—N1	0.0 (3)
C10—C5—C6—C7	−0.6 (4)	C12—C11—N2—C2	−0.4 (3)
C4—C5—C6—C7	−179.4 (2)	C13—C11—N2—C2	−179.1 (2)
C5—C6—C7—C8	0.6 (4)	N3—C2—N2—N1	−178.54 (18)
C6—C7—C8—C9	0.3 (4)	C3—C2—N2—N1	−0.4 (2)
C7—C8—C9—C10	−1.2 (4)	N3—C2—N2—C11	0.7 (3)
C8—C9—C10—C5	1.3 (4)	C3—C2—N2—C11	178.88 (19)
C6—C5—C10—C9	−0.4 (4)	C12—C1—N3—C2	−0.4 (3)
C4—C5—C10—C9	178.5 (2)	C14—C1—N3—C2	179.02 (19)
N2—C11—C12—C1	−0.3 (3)	C3—C2—N3—C1	−177.9 (2)
C13—C11—C12—C1	178.3 (2)	N2—C2—N3—C1	−0.3 (3)
N3—C1—C12—C11	0.7 (3)	O1—C14—O2—C15	1.4 (4)
C14—C1—C12—C11	−178.7 (2)	C1—C14—O2—C15	−178.5 (2)
N3—C1—C14—O1	158.1 (3)	C16—C15—O2—C14	147.1 (3)
C12—C1—C14—O1	−22.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1i	0.93	2.36	3.258 (3)	161
C6—H6···N3ii	0.93	2.62	3.507 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.93	2.36	3.258 (3)	161
C6—H6⋯N3ii	0.93	2.62	3.507 (3)	161

Symmetry codes: (i) ; (ii) .