Ethyl 5-methyl-7-phenyl-1,2,4-triazolo[4,3-a]pyrimidine-6-carboxyl-ate.

In the title compound, C15H14N4O2, the triazolo-pyrimidine ring system is almost planar (r.m.s. deviation = 0.02 Å) and the phenyl ring is inclined to its mean plane by 42.45 (9)°. The carboxyl group is inclined to the triazolo-pyrimidine ring mean plane by 57.8 (3)°. In the mol-ecule, there is a short C-H⋯O contact involving the carbonyl O atom and an H atom of the adjacent methyl substituent. In the crystal, neighbouring mol-ecules are linked by C-H⋯O hydrogen bonds, forming chains propagating along [010]. There are also weak π-π inter-actions present involving the pyridine and phenyl rings of neighbouring chains [inter-centroid distance = 3.8580 (16) Å].

Related literature

For information on annelated pyrimidine derivatives as promising vasodilating agents, see: Jeanneau-Nicolle et al. (1992 ▶); Ali et al. (2011 ▶). For details concerning triazolo­pyrimidines having anti­hypertensive and diuretic activity, see: Ali et al. (2011 ▶). For details of Biginelli di­hydro­pyrimidine calcium channel blockers, see: Rovnyak et al. (1995 ▶); Triggle & Padmanabhan (1995 ▶); Ohno et al. (2002 ▶). For potential ex vivo calcium-channel-blocking activity, see: Farghaly et al. (2013 ▶).

Experimental

Crystal data

C15H14N4O2

M = 282.30

Monoclinic,

a = 10.322 (2) Å

b = 8.1678 (19) Å

c = 16.798 (4) Å

β = 92.111 (4)°

V = 1415.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.10 × 0.10 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.610, T max = 0.991

12066 measured reflections

2550 independent reflections

1742 reflections with I > 2σ(I)

R int = 0.092

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.182

S = 1.07

2550 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.51 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku Americas and Rigaku, 2007 ▶); program(s) used to solve structure: SIR88 (Burla et al., 1989 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and CrystalStructure (Rigaku Americas and Rigaku, 2007 ▶); software used to prepare material for publication: SHELXL2013 and CrystalStructure.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814010113/su2724sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010113/su2724Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010113/su2724Isup3.cml

CCDC reference: 1000732

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H14N4O2	F(000) = 592
Mr = 282.30	Dx = 1.325 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
a = 10.322 (2) Å	Cell parameters from 10163 reflections
b = 8.1678 (19) Å	θ = 3.1–27.6°
c = 16.798 (4) Å	µ = 0.09 mm−1
β = 92.111 (4)°	T = 293 K
V = 1415.2 (5) Å3	Prism, colourless
Z = 4	0.30 × 0.10 × 0.10 mm

Rigaku SCXmini diffractometer	1742 reflections with I > 2σ(I)
ω scans	Rint = 0.092
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	θmax = 25.3°, θmin = 3.2°
Tmin = 0.610, Tmax = 0.991	h = −12→12
12066 measured reflections	k = −9→9
2550 independent reflections	l = −20→20

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.076	w = 1/[σ2(Fo2) + (0.1047P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.182	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.46 e Å−3
2550 reflections	Δρmin = −0.51 e Å−3
193 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.118 (11)

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.

	x	y	z	Uiso*/Ueq
O1	0.39205 (15)	0.6185 (2)	0.24879 (9)	0.0632 (5)
O2	0.51731 (19)	0.8413 (2)	0.24434 (12)	0.0817 (6)
N1	0.68299 (18)	0.3481 (2)	0.14373 (12)	0.0619 (6)
N2	0.65225 (18)	0.5557 (3)	0.04523 (11)	0.0602 (6)
N3	0.7530 (2)	0.3301 (3)	0.00856 (15)	0.0811 (7)
N4	0.6793 (2)	0.5809 (3)	−0.03304 (12)	0.0763 (7)
C1	0.7390 (3)	0.4421 (4)	−0.04963 (18)	0.0844 (9)
H1A	0.7702	0.4229	−0.1000	0.101*
C2	0.5898 (2)	0.6607 (3)	0.09427 (14)	0.0571 (6)
C3	0.6971 (2)	0.4037 (3)	0.06930 (15)	0.0631 (7)
C4	0.6228 (2)	0.4455 (3)	0.19354 (13)	0.0514 (6)
C5	0.5725 (2)	0.6021 (3)	0.16969 (13)	0.0512 (6)
C6	0.4935 (2)	0.7029 (3)	0.22516 (14)	0.0557 (6)
C7	0.3199 (3)	0.6916 (4)	0.31288 (18)	0.0855 (9)
H7A	0.3792	0.7412	0.3520	0.103*
H7B	0.2621	0.7759	0.2917	0.103*
C8	0.2453 (3)	0.5624 (4)	0.3499 (2)	0.1047 (11)
H8A	0.1806	0.5220	0.3123	0.157*
H8B	0.2040	0.6054	0.3957	0.157*
H8C	0.3023	0.4746	0.3660	0.157*
C9	0.5465 (3)	0.8207 (3)	0.06000 (17)	0.0752 (8)
H9A	0.6189	0.8944	0.0591	0.113*
H9B	0.4806	0.8665	0.0921	0.113*
H9C	0.5122	0.8044	0.0067	0.113*
C10	0.6102 (2)	0.3845 (3)	0.27599 (13)	0.0518 (6)
C11	0.6315 (2)	0.4852 (3)	0.34188 (15)	0.0604 (7)
H11	0.6588	0.5925	0.3347	0.073*
C12	0.6127 (2)	0.4282 (3)	0.41738 (16)	0.0716 (8)
H12	0.6269	0.4969	0.4609	0.086*
C13	0.5726 (3)	0.2680 (4)	0.42890 (17)	0.0764 (8)
H13	0.5570	0.2304	0.4799	0.092*
C14	0.5560 (2)	0.1660 (3)	0.36494 (18)	0.0735 (8)
H14	0.5313	0.0579	0.3728	0.088*
C15	0.5757 (2)	0.2217 (3)	0.28853 (15)	0.0594 (7)
H15	0.5659	0.1505	0.2455	0.071*

	U11	U22	U33	U12	U13	U23
O1	0.0658 (10)	0.0599 (10)	0.0652 (11)	−0.0005 (8)	0.0222 (8)	−0.0063 (8)
O2	0.0989 (14)	0.0453 (11)	0.1024 (15)	0.0022 (9)	0.0206 (11)	−0.0087 (9)
N1	0.0677 (12)	0.0523 (12)	0.0665 (14)	0.0044 (10)	0.0151 (10)	−0.0045 (10)
N2	0.0599 (12)	0.0686 (14)	0.0527 (12)	−0.0042 (10)	0.0113 (9)	0.0021 (10)
N3	0.0879 (16)	0.0836 (17)	0.0737 (16)	−0.0003 (13)	0.0294 (12)	−0.0176 (13)
N4	0.0772 (14)	0.0967 (18)	0.0560 (14)	−0.0106 (13)	0.0176 (11)	0.0007 (13)
C1	0.088 (2)	0.100 (2)	0.0668 (19)	−0.0110 (18)	0.0246 (15)	−0.0165 (18)
C2	0.0522 (13)	0.0566 (15)	0.0629 (16)	−0.0033 (11)	0.0078 (11)	0.0020 (12)
C3	0.0631 (15)	0.0613 (16)	0.0658 (17)	−0.0007 (12)	0.0139 (12)	−0.0080 (13)
C4	0.0514 (12)	0.0438 (13)	0.0594 (15)	−0.0020 (10)	0.0069 (10)	−0.0040 (11)
C5	0.0534 (13)	0.0459 (13)	0.0549 (14)	−0.0033 (10)	0.0091 (10)	0.0008 (10)
C6	0.0640 (14)	0.0447 (14)	0.0588 (14)	0.0064 (11)	0.0079 (11)	0.0044 (11)
C7	0.092 (2)	0.082 (2)	0.085 (2)	0.0076 (16)	0.0389 (16)	−0.0107 (16)
C8	0.110 (2)	0.115 (3)	0.092 (2)	−0.026 (2)	0.0457 (19)	−0.0211 (19)
C9	0.0748 (16)	0.0750 (19)	0.0764 (19)	0.0108 (14)	0.0102 (13)	0.0226 (14)
C10	0.0540 (13)	0.0447 (13)	0.0571 (14)	0.0039 (10)	0.0076 (10)	0.0006 (11)
C11	0.0666 (15)	0.0505 (14)	0.0639 (16)	−0.0002 (11)	−0.0017 (12)	−0.0025 (12)
C12	0.0791 (17)	0.0751 (18)	0.0602 (17)	0.0074 (14)	−0.0033 (13)	−0.0020 (14)
C13	0.0807 (18)	0.084 (2)	0.0649 (17)	0.0115 (16)	0.0091 (13)	0.0192 (16)
C14	0.0725 (17)	0.0602 (17)	0.089 (2)	0.0006 (13)	0.0147 (15)	0.0154 (15)
C15	0.0653 (14)	0.0440 (13)	0.0696 (16)	0.0002 (11)	0.0109 (12)	0.0017 (12)

O1—C6	1.327 (3)	C7—H7B	0.9700
O1—C7	1.459 (3)	C8—H8A	0.9600
O2—C6	1.198 (3)	C8—H8B	0.9600
N1—C4	1.325 (3)	C8—H8C	0.9600
N1—C3	1.343 (3)	C9—H9A	0.9600
N2—C2	1.367 (3)	C9—H9B	0.9600
N2—N4	1.370 (3)	C9—H9C	0.9600
N2—C3	1.380 (3)	C10—C11	1.390 (3)
N3—C3	1.334 (3)	C10—C15	1.395 (3)
N3—C1	1.343 (4)	C11—C12	1.372 (3)
N4—C1	1.325 (4)	C11—H11	0.9300
C1—H1A	0.9300	C12—C13	1.388 (4)
C2—C5	1.372 (3)	C12—H12	0.9300
C2—C9	1.490 (3)	C13—C14	1.365 (4)
C4—C5	1.432 (3)	C13—H13	0.9300
C4—C10	1.482 (3)	C14—C15	1.384 (3)
C5—C6	1.506 (3)	C14—H14	0.9300
C7—C8	1.459 (4)	C15—H15	0.9300
C7—H7A	0.9700
C6—O1—C7	116.0 (2)	C7—C8—H8A	109.5
C4—N1—C3	117.0 (2)	C7—C8—H8B	109.5
C2—N2—N4	127.0 (2)	H8A—C8—H8B	109.5
C2—N2—C3	123.3 (2)	C7—C8—H8C	109.5
N4—N2—C3	109.8 (2)	H8A—C8—H8C	109.5
C3—N3—C1	102.2 (3)	H8B—C8—H8C	109.5
C1—N4—N2	100.7 (2)	C2—C9—H9A	109.5
N4—C1—N3	117.9 (3)	C2—C9—H9B	109.5
N4—C1—H1A	121.0	H9A—C9—H9B	109.5
N3—C1—H1A	121.0	C2—C9—H9C	109.5
N2—C2—C5	114.7 (2)	H9A—C9—H9C	109.5
N2—C2—C9	117.3 (2)	H9B—C9—H9C	109.5
C5—C2—C9	128.0 (2)	C11—C10—C15	118.5 (2)
N3—C3—N1	128.6 (3)	C11—C10—C4	121.9 (2)
N3—C3—N2	109.4 (2)	C15—C10—C4	119.6 (2)
N1—C3—N2	122.0 (2)	C12—C11—C10	120.8 (2)
N1—C4—C5	122.2 (2)	C12—C11—H11	119.6
N1—C4—C10	116.6 (2)	C10—C11—H11	119.6
C5—C4—C10	121.20 (18)	C11—C12—C13	120.1 (3)
C2—C5—C4	120.8 (2)	C11—C12—H12	119.9
C2—C5—C6	118.2 (2)	C13—C12—H12	119.9
C4—C5—C6	120.97 (19)	C14—C13—C12	119.7 (3)
O2—C6—O1	124.5 (2)	C14—C13—H13	120.2
O2—C6—C5	124.9 (2)	C12—C13—H13	120.2
O1—C6—C5	110.6 (2)	C13—C14—C15	120.7 (3)
C8—C7—O1	108.1 (2)	C13—C14—H14	119.6
C8—C7—H7A	110.1	C15—C14—H14	119.6
O1—C7—H7A	110.1	C14—C15—C10	120.0 (2)
C8—C7—H7B	110.1	C14—C15—H15	120.0
O1—C7—H7B	110.1	C10—C15—H15	120.0
H7A—C7—H7B	108.4
C2—N2—N4—C1	−179.8 (2)	C10—C4—C5—C2	177.0 (2)
C3—N2—N4—C1	−0.3 (2)	N1—C4—C5—C6	174.1 (2)
N2—N4—C1—N3	0.3 (3)	C10—C4—C5—C6	−6.1 (3)
C3—N3—C1—N4	−0.2 (3)	C7—O1—C6—O2	−11.1 (3)
N4—N2—C2—C5	178.28 (19)	C7—O1—C6—C5	170.1 (2)
C3—N2—C2—C5	−1.2 (3)	C2—C5—C6—O2	−58.0 (3)
N4—N2—C2—C9	−0.4 (3)	C4—C5—C6—O2	125.1 (3)
C3—N2—C2—C9	−179.9 (2)	C2—C5—C6—O1	120.8 (2)
C1—N3—C3—N1	−179.8 (3)	C4—C5—C6—O1	−56.1 (3)
C1—N3—C3—N2	0.0 (3)	C6—O1—C7—C8	−159.8 (2)
C4—N1—C3—N3	−179.8 (2)	N1—C4—C10—C11	137.2 (2)
C4—N1—C3—N2	0.5 (3)	C5—C4—C10—C11	−42.6 (3)
C2—N2—C3—N3	179.8 (2)	N1—C4—C10—C15	−42.9 (3)
N4—N2—C3—N3	0.2 (3)	C5—C4—C10—C15	137.3 (2)
C2—N2—C3—N1	−0.4 (4)	C15—C10—C11—C12	−3.2 (3)
N4—N2—C3—N1	−180.0 (2)	C4—C10—C11—C12	176.6 (2)
C3—N1—C4—C5	1.1 (3)	C10—C11—C12—C13	0.3 (4)
C3—N1—C4—C10	−178.75 (19)	C11—C12—C13—C14	2.2 (4)
N2—C2—C5—C4	2.6 (3)	C12—C13—C14—C15	−1.7 (4)
C9—C2—C5—C4	−178.8 (2)	C13—C14—C15—C10	−1.3 (4)
N2—C2—C5—C6	−174.28 (19)	C11—C10—C15—C14	3.7 (3)
C9—C2—C5—C6	4.3 (4)	C4—C10—C15—C14	−176.1 (2)
N1—C4—C5—C2	−2.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O2	0.96	2.58	3.127 (4)	116
C15—H15···O2i	0.93	2.57	3.246 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O2	0.96	2.58	3.127 (4)	116
C15—H15⋯O2i	0.93	2.57	3.246 (3)	129

Symmetry code: (i) .