3-Methyl-4-(2-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-7-yl)furazan.

In the title mol-ecule, C14H10N6O, the planes of the methyl-furazan fragment and the phenyl ring attached to the triazolo-pyrimidine bicycle are twisted from the mean plane of the bicycle at angles of 45.92 (5) and 5.45 (4)°, respectively. In the crystal, π-π inter-actions, indicated by short distances [in the range 3.456 (3)-3.591 (3) Å] between the centroids of the five- and six-membered rings of neighbouring mol-ecules, link the mol-ecules into stacks propagating along the c-axis direction.

Related literature

For applications of enamino­nes in synthesis, see: Kulinich & Ischenko (2009 ▶); Stanovnik & Svete (2004 ▶). For the synthesis of triazolo­pyrimidines from enamino­propenones, see: Abdelhamid et al. (2012 ▶, 2013 ▶); Behbehani & Ibrahim (2012 ▶). For X-ray studies of [1,2,4]triazolo[a]pyrimidines, see: Lipkind et al. (2011 ▶); Shikhaliev et al. (2008 ▶); Lokaj et al. (2006 ▶) and of furazan derivatives, see: Sheremetev et al. (2004 ▶, 2006 ▶, 2012 ▶, 2013 ▶); Suponitsky et al. (2009a ▶,b ▶). For normal values of bond lengths in organic compounds, see: Allen et al. (1987 ▶) and for a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C14H10N6O

M = 278.28

Monoclinic,

a = 11.1397 (6) Å

b = 15.6579 (8) Å

c = 7.3952 (4) Å

β = 101.332 (1)°

V = 1264.76 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 120 K

0.32 × 0.28 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer

16844 measured reflections

4041 independent reflections

3456 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.118

S = 1.02

4041 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.28 e Å−3

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

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813027700/cv5430sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813027700/cv5430Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027700/cv5430Isup3.cml

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

C14H10N6O	F(000) = 576
Mr = 278.28	Dx = 1.461 Mg m−3
Monoclinic, P21/c	Melting point = 483–482 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.1397 (6) Å	Cell parameters from 7123 reflections
b = 15.6579 (8) Å	θ = 2.3–31.0°
c = 7.3952 (4) Å	µ = 0.10 mm−1
β = 101.332 (1)°	T = 120 K
V = 1264.76 (12) Å3	Prizm, colourless
Z = 4	0.32 × 0.28 × 0.26 mm

Bruker APEXII CCD diffractometer	3456 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.030
Graphite monochromator	θmax = 31.0°, θmin = 1.9°
φ and ω scans	h = −16→16
16844 measured reflections	k = −22→21
4041 independent reflections	l = −10→10

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0678P)2 + 0.3512P] where P = (Fo2 + 2Fc2)/3
4041 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.28 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
O1	0.56608 (7)	0.23558 (5)	0.09319 (14)	0.0282 (2)
N1	1.00892 (7)	−0.06092 (5)	0.21751 (12)	0.01583 (17)
N2	0.82706 (8)	−0.11973 (6)	0.02377 (12)	0.01834 (18)
N3	0.84903 (7)	0.02462 (5)	0.13466 (11)	0.01300 (16)
N4	0.93391 (7)	0.07409 (5)	0.24376 (11)	0.01399 (16)
N5	0.58150 (8)	0.14848 (6)	0.09470 (14)	0.0227 (2)
N6	0.67069 (8)	0.27675 (6)	0.06085 (15)	0.0239 (2)
C1	1.02813 (8)	0.01935 (6)	0.28809 (13)	0.01377 (17)
C2	0.89448 (9)	−0.05739 (6)	0.12102 (13)	0.01468 (18)
C3	0.71487 (9)	−0.09738 (6)	−0.05783 (14)	0.01883 (19)
H3A	0.6646	−0.1399	−0.1265	0.023*
C4	0.66417 (9)	−0.01483 (6)	−0.05042 (13)	0.01698 (19)
H4A	0.5829	−0.0031	−0.1129	0.020*
C5	0.73399 (8)	0.04786 (6)	0.04821 (13)	0.01414 (17)
C6	1.14510 (8)	0.04615 (6)	0.40276 (13)	0.01413 (17)
C7	1.23825 (9)	−0.01412 (6)	0.45314 (14)	0.01694 (19)
H7A	1.2241	−0.0721	0.4178	0.020*
C8	1.35164 (9)	0.01047 (7)	0.55480 (15)	0.0205 (2)
H8A	1.4147	−0.0307	0.5887	0.025*
C9	1.37265 (10)	0.09538 (8)	0.60680 (16)	0.0247 (2)
H9A	1.4504	0.1124	0.6748	0.030*
C10	1.27942 (10)	0.15534 (7)	0.55890 (17)	0.0262 (2)
H10A	1.2935	0.2132	0.5960	0.031*
C11	1.16591 (9)	0.13117 (7)	0.45715 (15)	0.0202 (2)
H11A	1.1027	0.1724	0.4247	0.024*
C12	0.69232 (9)	0.13591 (6)	0.06503 (13)	0.01574 (18)
C13	0.74940 (9)	0.21662 (6)	0.04368 (14)	0.01690 (19)
C14	0.87253 (9)	0.23617 (7)	0.00342 (15)	0.0197 (2)
H14A	0.8730	0.2945	−0.0444	0.030*
H14B	0.8910	0.1958	−0.0887	0.030*
H14C	0.9345	0.2310	0.1169	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0170 (4)	0.0169 (4)	0.0508 (5)	0.0032 (3)	0.0073 (3)	−0.0001 (3)
N1	0.0163 (4)	0.0127 (4)	0.0189 (4)	0.0008 (3)	0.0044 (3)	−0.0004 (3)
N2	0.0204 (4)	0.0139 (4)	0.0210 (4)	−0.0017 (3)	0.0048 (3)	−0.0031 (3)
N3	0.0129 (3)	0.0107 (3)	0.0156 (3)	−0.0004 (3)	0.0032 (3)	−0.0006 (3)
N4	0.0126 (3)	0.0128 (3)	0.0164 (4)	−0.0012 (3)	0.0023 (3)	−0.0010 (3)
N5	0.0162 (4)	0.0155 (4)	0.0359 (5)	0.0014 (3)	0.0036 (4)	0.0000 (3)
N6	0.0185 (4)	0.0154 (4)	0.0372 (5)	0.0013 (3)	0.0040 (4)	0.0016 (4)
C1	0.0139 (4)	0.0129 (4)	0.0153 (4)	0.0001 (3)	0.0050 (3)	0.0010 (3)
C2	0.0169 (4)	0.0114 (4)	0.0168 (4)	0.0007 (3)	0.0058 (3)	−0.0004 (3)
C3	0.0205 (4)	0.0147 (4)	0.0211 (4)	−0.0034 (3)	0.0038 (4)	−0.0034 (3)
C4	0.0164 (4)	0.0158 (4)	0.0182 (4)	−0.0022 (3)	0.0022 (3)	−0.0011 (3)
C5	0.0138 (4)	0.0133 (4)	0.0154 (4)	−0.0002 (3)	0.0031 (3)	0.0011 (3)
C6	0.0126 (4)	0.0144 (4)	0.0160 (4)	0.0000 (3)	0.0045 (3)	0.0017 (3)
C7	0.0157 (4)	0.0165 (4)	0.0192 (4)	0.0016 (3)	0.0049 (3)	0.0037 (3)
C8	0.0145 (4)	0.0233 (5)	0.0233 (5)	0.0013 (4)	0.0026 (4)	0.0067 (4)
C9	0.0168 (4)	0.0266 (5)	0.0283 (5)	−0.0043 (4)	−0.0016 (4)	0.0042 (4)
C10	0.0222 (5)	0.0192 (5)	0.0340 (6)	−0.0043 (4)	−0.0018 (4)	−0.0021 (4)
C11	0.0169 (4)	0.0159 (4)	0.0269 (5)	0.0005 (3)	0.0020 (4)	−0.0009 (4)
C12	0.0140 (4)	0.0136 (4)	0.0184 (4)	0.0003 (3)	0.0004 (3)	0.0006 (3)
C13	0.0172 (4)	0.0132 (4)	0.0193 (4)	0.0003 (3)	0.0012 (3)	0.0011 (3)
C14	0.0203 (4)	0.0154 (4)	0.0243 (5)	−0.0012 (3)	0.0068 (4)	0.0030 (4)

O1—N5	1.3742 (12)	C5—C12	1.4678 (13)
O1—N6	1.3929 (12)	C6—C11	1.3968 (14)
N1—C2	1.3342 (12)	C6—C7	1.3979 (13)
N1—C1	1.3616 (12)	C7—C8	1.3914 (14)
N2—C3	1.3236 (13)	C7—H7A	0.9500
N2—C2	1.3497 (12)	C8—C9	1.3910 (16)
N3—N4	1.3583 (11)	C8—H8A	0.9500
N3—C5	1.3643 (12)	C9—C10	1.3931 (16)
N3—C2	1.3912 (12)	C9—H9A	0.9500
N4—C1	1.3449 (12)	C10—C11	1.3909 (14)
N5—C12	1.3106 (13)	C10—H10A	0.9500
N6—C13	1.3095 (13)	C11—H11A	0.9500
C1—C6	1.4693 (13)	C12—C13	1.4373 (13)
C3—C4	1.4160 (14)	C13—C14	1.4914 (14)
C3—H3A	0.9500	C14—H14A	0.9800
C4—C5	1.3702 (13)	C14—H14B	0.9800
C4—H4A	0.9500	C14—H14C	0.9800
Cg1···Cg1i	3.456 (2)	Cg1···Cg3ii	3.591 (2)
Cg2···Cg3ii	3.540 (2)
N5—O1—N6	110.69 (8)	C8—C7—C6	120.31 (9)
C2—N1—C1	103.20 (8)	C8—C7—H7A	119.8
C3—N2—C2	115.36 (9)	C6—C7—H7A	119.8
N4—N3—C5	127.33 (8)	C7—C8—C9	119.96 (9)
N4—N3—C2	110.41 (8)	C7—C8—H8A	120.0
C5—N3—C2	122.26 (8)	C9—C8—H8A	120.0
C1—N4—N3	101.55 (7)	C10—C9—C8	119.82 (10)
C12—N5—O1	105.55 (8)	C10—C9—H9A	120.1
C13—N6—O1	106.41 (8)	C8—C9—H9A	120.1
N4—C1—N1	116.01 (8)	C11—C10—C9	120.48 (10)
N4—C1—C6	121.32 (8)	C11—C10—H10A	119.8
N1—C1—C6	122.66 (8)	C9—C10—H10A	119.8
N1—C2—N2	128.91 (9)	C10—C11—C6	119.80 (10)
N1—C2—N3	108.82 (8)	C10—C11—H11A	120.1
N2—C2—N3	122.27 (9)	C6—C11—H11A	120.1
N2—C3—C4	124.87 (9)	N5—C12—C13	109.75 (9)
N2—C3—H3A	117.6	N5—C12—C5	118.64 (9)
C4—C3—H3A	117.6	C13—C12—C5	131.49 (9)
C5—C4—C3	119.05 (9)	N6—C13—C12	107.61 (9)
C5—C4—H4A	120.5	N6—C13—C14	122.10 (9)
C3—C4—H4A	120.5	C12—C13—C14	130.27 (9)
N3—C5—C4	116.17 (9)	C13—C14—H14A	109.5
N3—C5—C12	119.63 (8)	C13—C14—H14B	109.5
C4—C5—C12	124.20 (9)	H14A—C14—H14B	109.5
C11—C6—C7	119.61 (9)	C13—C14—H14C	109.5
C11—C6—C1	121.11 (9)	H14A—C14—H14C	109.5
C7—C6—C1	119.25 (9)	H14B—C14—H14C	109.5
C5—N3—N4—C1	−179.38 (9)	N4—C1—C6—C11	−5.31 (14)
C2—N3—N4—C1	1.14 (9)	N1—C1—C6—C11	173.36 (9)
N6—O1—N5—C12	0.26 (12)	N4—C1—C6—C7	176.72 (9)
N5—O1—N6—C13	−0.33 (12)	N1—C1—C6—C7	−4.61 (13)
N3—N4—C1—N1	−0.77 (10)	C11—C6—C7—C8	−0.83 (14)
N3—N4—C1—C6	177.98 (8)	C1—C6—C7—C8	177.17 (9)
C2—N1—C1—N4	0.08 (11)	C6—C7—C8—C9	0.02 (15)
C2—N1—C1—C6	−178.65 (8)	C7—C8—C9—C10	0.85 (17)
C1—N1—C2—N2	−178.95 (10)	C8—C9—C10—C11	−0.91 (18)
C1—N1—C2—N3	0.65 (10)	C9—C10—C11—C6	0.09 (17)
C3—N2—C2—N1	179.64 (9)	C7—C6—C11—C10	0.77 (15)
C3—N2—C2—N3	0.09 (14)	C1—C6—C11—C10	−177.19 (10)
N4—N3—C2—N1	−1.19 (10)	O1—N5—C12—C13	−0.09 (12)
C5—N3—C2—N1	179.29 (8)	O1—N5—C12—C5	−176.58 (9)
N4—N3—C2—N2	178.44 (8)	N3—C5—C12—N5	−136.53 (10)
C5—N3—C2—N2	−1.08 (14)	C4—C5—C12—N5	43.38 (14)
C2—N2—C3—C4	0.60 (15)	N3—C5—C12—C13	47.89 (15)
N2—C3—C4—C5	−0.33 (15)	C4—C5—C12—C13	−132.19 (11)
N4—N3—C5—C4	−178.14 (9)	O1—N6—C13—C12	0.26 (11)
C2—N3—C5—C4	1.30 (13)	O1—N6—C13—C14	178.61 (9)
N4—N3—C5—C12	1.79 (14)	N5—C12—C13—N6	−0.11 (12)
C2—N3—C5—C12	−178.78 (8)	C5—C12—C13—N6	175.77 (10)
C3—C4—C5—N3	−0.63 (13)	N5—C12—C13—C14	−178.28 (10)
C3—C4—C5—C12	179.46 (9)	C5—C12—C13—C14	−2.40 (18)