2-Méthyl-3-(3-méthyl-1H-pyrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one

The structure of the title compound, C₁₃H₁₂N₄O, shows that the molecule adopts a flat conformation. There is an intermolecular hydrogen bond between the NH function of the pyrazole ring and the O atom of the pyridopyrimidinone group.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.112
• Data-to-parameter ratio = 13.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: KappaCCD Software; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

2-Méthyl-3-(3-méthyl-1H-pyrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one

Crystal data

C13H12N4O	F(000) = 1008
Mr = 240.27	Dx = 1.398 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 15817 reflections
a = 28.400 (7) Å	θ = 1–26°
b = 5.1148 (2) Å	µ = 0.09 mm^−1
c = 18.321 (4) Å	T = 293 K
β = 120.93 (1)°	Prism, yellow
V = 2282.9 (8) Å^3	0.35 × 0.25 × 0.15 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	1895 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Graphite monochromator	θmax = 26.0°, θmin = 3.7°
φ scans	h = 0→34
15817 measured reflections	k = 0→6
2201 independent reflections	l = −22→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0585P)^2 + 0.8769P] where P = (Fo^2 + 2Fc^2)/3
2201 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O18	0.71357 (3)	0.5390 (2)	0.49797 (6)	0.0504 (3)
N1	0.66295 (5)	0.9284 (3)	0.39253 (7)	0.0517 (3)
H1	0.6946	0.8560	0.4223	0.062*
N2	0.65176 (5)	1.1111 (3)	0.33253 (8)	0.0573 (3)
N8	0.58745 (4)	0.4522 (2)	0.53973 (7)	0.0447 (3)
C3	0.59965 (6)	1.1712 (3)	0.30182 (8)	0.0472 (3)
C4	0.57811 (5)	1.0288 (3)	0.34266 (9)	0.0482 (3)
H4	0.5425	1.0384	0.3324	0.058*
C5	0.61986 (5)	0.8701 (2)	0.40151 (7)	0.0380 (3)
C6	0.62391 (4)	0.6735 (2)	0.46281 (7)	0.0364 (3)
C7	0.58311 (5)	0.6322 (2)	0.48284 (8)	0.0398 (3)
C9	0.63191 (5)	0.3042 (3)	0.57858 (8)	0.0408 (3)
C10	0.63808 (6)	0.1166 (3)	0.63968 (9)	0.0519 (4)
H10	0.6108	0.1002	0.6530	0.062*
C11	0.68272 (6)	−0.0391 (3)	0.67900 (9)	0.0541 (4)
H11	0.6861	−0.1603	0.7193	0.065*
C12	0.72413 (6)	−0.0168 (3)	0.65867 (9)	0.0520 (4)
H12	0.7545	−0.1267	0.6844	0.062*
C13	0.71959 (5)	0.1638 (3)	0.60198 (8)	0.0458 (3)
H13	0.7472	0.1791	0.5891	0.055*
N14	0.67447 (4)	0.3269 (2)	0.56276 (6)	0.0376 (3)
C15	0.67290 (5)	0.5203 (2)	0.50516 (8)	0.0377 (3)
C16	0.57207 (7)	1.3712 (3)	0.23323 (10)	0.0645 (4)
H16A	0.5992	1.4847	0.2339	0.097*	0.52 (2)
H16B	0.5472	1.4722	0.2427	0.097*	0.52 (2)
H16C	0.5521	1.2855	0.1790	0.097*	0.52 (2)
H16E	0.5798	1.5429	0.2580	0.097*	0.48 (2)
H16F	0.5331	1.3421	0.2025	0.097*	0.48 (2)
H16D	0.5855	1.3576	0.1949	0.097*	0.48 (2)
C17	0.53095 (5)	0.7859 (3)	0.44440 (10)	0.0536 (4)
H17A	0.5102	0.7339	0.4699	0.080*
H17B	0.5098	0.7537	0.3843	0.080*
H17C	0.5394	0.9689	0.4544	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O18	0.0386 (5)	0.0573 (6)	0.0668 (6)	0.0053 (4)	0.0352 (5)	0.0103 (5)
N1	0.0376 (6)	0.0707 (8)	0.0508 (6)	0.0050 (5)	0.0257 (5)	0.0164 (6)
N2	0.0507 (7)	0.0725 (8)	0.0525 (7)	0.0000 (6)	0.0292 (6)	0.0156 (6)
N8	0.0401 (6)	0.0484 (6)	0.0552 (6)	−0.0036 (5)	0.0314 (5)	−0.0020 (5)
C3	0.0489 (7)	0.0489 (7)	0.0431 (6)	0.0001 (6)	0.0232 (6)	−0.0009 (6)
C4	0.0397 (7)	0.0537 (8)	0.0524 (7)	0.0042 (6)	0.0245 (6)	0.0049 (6)
C5	0.0342 (6)	0.0433 (6)	0.0391 (6)	−0.0036 (5)	0.0206 (5)	−0.0057 (5)
C6	0.0312 (6)	0.0404 (6)	0.0391 (6)	−0.0043 (5)	0.0193 (5)	−0.0065 (5)
C7	0.0339 (6)	0.0427 (7)	0.0465 (6)	−0.0060 (5)	0.0233 (5)	−0.0078 (5)
C9	0.0400 (6)	0.0435 (7)	0.0438 (6)	−0.0078 (5)	0.0250 (5)	−0.0072 (5)
C10	0.0572 (8)	0.0557 (8)	0.0534 (8)	−0.0081 (7)	0.0361 (7)	−0.0008 (7)
C11	0.0617 (9)	0.0530 (8)	0.0460 (7)	−0.0047 (7)	0.0266 (7)	0.0042 (6)
C12	0.0474 (7)	0.0508 (8)	0.0485 (7)	0.0010 (6)	0.0179 (6)	0.0035 (6)
C13	0.0368 (6)	0.0485 (7)	0.0498 (7)	−0.0002 (5)	0.0208 (6)	−0.0010 (6)
N14	0.0337 (5)	0.0405 (5)	0.0400 (5)	−0.0036 (4)	0.0200 (4)	−0.0041 (4)
C15	0.0340 (6)	0.0412 (6)	0.0425 (6)	−0.0042 (5)	0.0229 (5)	−0.0047 (5)
C16	0.0697 (10)	0.0633 (9)	0.0583 (9)	0.0085 (8)	0.0313 (8)	0.0136 (8)
C17	0.0390 (7)	0.0584 (8)	0.0727 (9)	0.0024 (6)	0.0354 (7)	0.0038 (7)

Geometric parameters (Å, º)

O18—C15	1.2316 (14)	C6—C7	1.3996 (16)
N1—C5	1.3493 (16)	C6—C15	1.4289 (17)
N1—N2	1.3500 (16)	C7—C17	1.4955 (18)
N2—C3	1.3211 (18)	C9—N14	1.3852 (15)
N8—C9	1.3229 (17)	C9—C10	1.4151 (19)
N8—C7	1.3480 (17)	C10—C11	1.349 (2)
C3—C4	1.3911 (19)	C11—C12	1.409 (2)
C3—C16	1.493 (2)	C12—C13	1.3460 (19)
C4—C5	1.3831 (18)	C13—N14	1.3809 (16)
C5—C6	1.4674 (17)	N14—C15	1.4305 (16)
C5—N1—N2	113.80 (11)	C6—C7—C17	123.39 (12)
C3—N2—N1	104.55 (11)	N8—C9—N14	122.27 (11)
C9—N8—C7	119.30 (10)	N8—C9—C10	120.63 (11)
N2—C3—C4	110.80 (12)	N14—C9—C10	117.09 (12)
N2—C3—C16	120.43 (13)	C11—C10—C9	121.53 (13)
C4—C3—C16	128.77 (13)	C10—C11—C12	119.60 (13)
C5—C4—C3	106.78 (12)	C13—C12—C11	119.83 (13)
N1—C5—C4	104.07 (11)	C12—C13—N14	120.75 (12)
N1—C5—C6	121.72 (11)	C13—N14—C9	121.12 (11)
C4—C5—C6	134.20 (11)	C13—N14—C15	118.05 (10)
C7—C6—C15	118.76 (11)	C9—N14—C15	120.83 (10)
C7—C6—C5	123.67 (11)	O18—C15—C6	127.18 (12)
C15—C6—C5	117.56 (10)	O18—C15—N14	117.21 (11)
N8—C7—C6	123.15 (11)	C6—C15—N14	115.62 (10)
N8—C7—C17	113.45 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O18^i	0.86	2.30	3.0196 (16)	141

Symmetry code: (i) −x+3/2, −y+3/2, −z+1.