12-(4-Methoxy-phen-yl)-10-phenyl-3,4,5,6,8,10-hexa-azatricyclo-[7.3.0.0]dodeca-1(9),2,4,7,11-penta-ene.

In the title compound, C(19)H(14)N(6)O, the fused 12-membered tetra-zolo/pyrimidine/pyrrole ring system is almost planar (r.m.s. deviation = 0.013 Å). The 4-methoxy-phenyl and phenyl substituents on the pyrrole ring are both twisted with respect to the fused-ring system [dihedral angles = 25.39 (18) and 36.42 (18)°, respectively]. Intra-molecular C-H⋯N inter-actions occur. In the crystal, mol-ecules pack into layers in the ac plane and these are connected along the b axis via C-H⋯π and π-π [centroid-centroid separation = 3.608 (3) Å] inter-actions.

Related literature

For background to the biological activity of fused tetra­zolopyrimidines, see: Shishoo & Jain (1992 ▶); Desai & Shah (2006 ▶). For related structures, see: Jotani et al. (2010a ▶,b ▶); Shah et al. (2010 ▶). For semi-empirical quantum chemical calculations, see: Stewart (2009 ▶).

Experimental

Crystal data

C19H14N6O

M = 342.36

Orthorhombic,

a = 9.3537 (7) Å

b = 23.6045 (19) Å

c = 7.1543 (6) Å

V = 1579.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.35 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.981

16155 measured reflections

1666 independent reflections

1344 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.142

S = 1.12

1666 reflections

236 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681000869X/hb5355sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000869X/hb5355Isup2.hkl

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

C19H14N6O	F(000) = 712
Mr = 342.36	Dx = 1.440 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2330 reflections
a = 9.3537 (7) Å	θ = 2.0–32.0°
b = 23.6045 (19) Å	µ = 0.10 mm−1
c = 7.1543 (6) Å	T = 293 K
V = 1579.6 (2) Å3	Block, colourless
Z = 4	0.35 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	1666 independent reflections
Radiation source: fine-focus sealed tube	1344 reflections with I > 2σ(I)
graphite	Rint = 0.051
ω and φ scan	θmax = 25.9°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
Tmin = 0.967, Tmax = 0.981	k = −28→26
16155 measured reflections	l = −8→8

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0924P)2 + 0.1003P] where P = (Fo2 + 2Fc2)/3
1666 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.50 e Å−3
1 restraint	Δρmin = −0.27 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.1311 (2)	−0.24532 (10)	0.1991 (5)	0.0436 (7)
N1	0.6887 (3)	0.03688 (12)	0.2217 (6)	0.0388 (7)
N2	0.8226 (3)	0.01376 (15)	0.2170 (8)	0.0538 (9)
N3	0.8028 (3)	−0.04038 (15)	0.2108 (8)	0.0570 (10)
N4	0.6627 (3)	−0.05488 (13)	0.2095 (7)	0.0490 (9)
N5	0.5225 (3)	0.11037 (11)	0.2330 (6)	0.0394 (8)
N6	0.2784 (3)	0.07783 (11)	0.2260 (5)	0.0345 (7)
C1	0.6538 (4)	0.09319 (16)	0.2303 (7)	0.0434 (9)
H1	0.7269	0.1199	0.2342	0.052*
C2	0.5911 (3)	−0.00622 (14)	0.2167 (8)	0.0368 (8)
C3	0.4447 (3)	0.00972 (13)	0.2204 (7)	0.0326 (7)
C4	0.4226 (3)	0.06828 (13)	0.2276 (7)	0.0338 (8)
C5	0.2112 (3)	0.02605 (13)	0.2160 (7)	0.0374 (8)
H5	0.1126	0.0211	0.2128	0.045*
C6	0.3086 (3)	−0.01734 (14)	0.2112 (7)	0.0348 (8)
C7	0.2701 (3)	−0.07795 (14)	0.2027 (7)	0.0336 (8)
C8	0.3593 (4)	−0.12011 (15)	0.2688 (6)	0.0413 (11)
H8	0.4494	−0.1105	0.3136	0.050*
C9	0.3172 (4)	−0.17651 (15)	0.2697 (7)	0.0430 (11)
H9	0.3781	−0.2043	0.3161	0.052*
C10	0.1848 (4)	−0.19110 (13)	0.2015 (7)	0.0356 (8)
C11	0.0954 (4)	−0.14989 (15)	0.1288 (6)	0.0380 (9)
H11	0.0071	−0.1597	0.0786	0.046*
C12	0.1390 (4)	−0.09411 (16)	0.1317 (7)	0.0382 (9)
H12	0.0782	−0.0665	0.0842	0.046*
C13	0.2110 (4)	−0.28780 (15)	0.2954 (7)	0.0487 (11)
H13A	0.3060	−0.2896	0.2449	0.073*
H13B	0.1650	−0.3239	0.2802	0.073*
H13C	0.2157	−0.2785	0.4259	0.073*
C14	0.2042 (3)	0.13107 (13)	0.2232 (7)	0.0339 (8)
C15	0.2549 (4)	0.17606 (15)	0.3270 (7)	0.0375 (9)
H15	0.3365	0.1721	0.4002	0.045*
C16	0.1822 (4)	0.22714 (15)	0.3202 (7)	0.0448 (10)
H16	0.2173	0.2582	0.3860	0.054*
C17	0.0586 (4)	0.23249 (15)	0.2172 (8)	0.0462 (9)
H17	0.0097	0.2668	0.2137	0.055*
C18	0.0080 (4)	0.18610 (15)	0.1186 (7)	0.0456 (10)
H18	−0.0765	0.1892	0.0511	0.055*
C19	0.0800 (4)	0.13608 (15)	0.1191 (7)	0.0405 (9)
H19	0.0461	0.1055	0.0502	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0420 (14)	0.0314 (12)	0.057 (2)	−0.0069 (10)	−0.0019 (15)	0.0016 (15)
N1	0.0246 (14)	0.0442 (16)	0.048 (2)	0.0005 (12)	−0.0045 (17)	0.0019 (19)
N2	0.0259 (15)	0.062 (2)	0.073 (3)	0.0029 (14)	0.003 (2)	0.000 (3)
N3	0.0294 (16)	0.057 (2)	0.085 (3)	0.0061 (14)	0.005 (2)	0.000 (3)
N4	0.0281 (15)	0.0476 (19)	0.071 (3)	0.0056 (12)	0.0001 (18)	−0.002 (2)
N5	0.0326 (15)	0.0351 (15)	0.050 (2)	−0.0048 (12)	−0.0031 (17)	0.0032 (18)
N6	0.0292 (14)	0.0285 (14)	0.046 (2)	0.0018 (10)	−0.0029 (17)	0.0011 (16)
C1	0.0353 (19)	0.044 (2)	0.051 (3)	−0.0068 (15)	−0.003 (2)	0.002 (2)
C2	0.0297 (16)	0.0390 (18)	0.042 (2)	0.0006 (14)	0.001 (2)	−0.001 (2)
C3	0.0287 (16)	0.0324 (16)	0.0366 (19)	0.0006 (13)	0.001 (2)	−0.001 (2)
C4	0.0301 (16)	0.0333 (17)	0.038 (2)	−0.0008 (13)	−0.0004 (18)	0.0011 (19)
C5	0.0277 (16)	0.0322 (18)	0.052 (2)	−0.0003 (13)	0.000 (2)	−0.002 (2)
C6	0.0284 (16)	0.0319 (17)	0.044 (2)	0.0006 (13)	0.000 (2)	0.004 (2)
C7	0.0290 (17)	0.0308 (17)	0.041 (2)	0.0017 (13)	0.0057 (18)	−0.0007 (18)
C8	0.0305 (19)	0.038 (2)	0.055 (3)	−0.0003 (15)	−0.0042 (17)	−0.0009 (18)
C9	0.034 (2)	0.0303 (18)	0.065 (3)	0.0055 (15)	−0.0018 (19)	0.0029 (18)
C10	0.0358 (18)	0.0299 (17)	0.041 (2)	−0.0039 (13)	0.0079 (19)	−0.0023 (18)
C11	0.0292 (17)	0.042 (2)	0.042 (2)	−0.0046 (15)	−0.0006 (17)	0.0028 (19)
C12	0.0294 (18)	0.0359 (19)	0.049 (2)	0.0050 (15)	0.0026 (18)	0.0034 (18)
C13	0.059 (3)	0.0315 (19)	0.055 (3)	0.0006 (18)	0.003 (2)	0.0022 (19)
C14	0.0313 (17)	0.0298 (16)	0.041 (2)	0.0008 (13)	0.002 (2)	0.0026 (19)
C15	0.0334 (19)	0.0349 (19)	0.044 (2)	0.0012 (15)	−0.0025 (17)	0.0013 (18)
C16	0.048 (2)	0.035 (2)	0.051 (3)	0.0011 (17)	0.002 (2)	−0.0088 (19)
C17	0.047 (2)	0.0377 (19)	0.054 (3)	0.0110 (15)	0.003 (2)	0.001 (2)
C18	0.038 (2)	0.043 (2)	0.056 (3)	0.0061 (16)	−0.010 (2)	0.004 (2)
C19	0.038 (2)	0.0316 (18)	0.052 (3)	−0.0037 (15)	−0.006 (2)	−0.0005 (18)

O1—C10	1.375 (4)	C8—C9	1.388 (5)
O1—C13	1.428 (5)	C8—H8	0.9300
N1—N2	1.367 (4)	C9—C10	1.374 (5)
N1—C2	1.367 (4)	C9—H9	0.9300
N1—C1	1.370 (5)	C10—C11	1.384 (5)
N2—N3	1.292 (5)	C11—C12	1.379 (5)
N3—N4	1.355 (4)	C11—H11	0.9300
N4—C2	1.330 (4)	C12—H12	0.9300
N5—C1	1.294 (4)	C13—H13A	0.9600
N5—C4	1.364 (4)	C13—H13B	0.9600
N6—C4	1.368 (4)	C13—H13C	0.9600
N6—C5	1.376 (4)	C14—C15	1.380 (5)
N6—C14	1.435 (4)	C14—C19	1.385 (5)
C1—H1	0.9300	C15—C16	1.385 (5)
C2—C3	1.420 (4)	C15—H15	0.9300
C3—C4	1.399 (5)	C16—C17	1.377 (6)
C3—C6	1.426 (4)	C16—H16	0.9300
C5—C6	1.371 (4)	C17—C18	1.386 (6)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.477 (4)	C18—C19	1.359 (5)
C7—C12	1.380 (5)	C18—H18	0.9300
C7—C8	1.382 (5)	C19—H19	0.9300
C10—O1—C13	117.2 (3)	C10—C9—H9	120.2
N2—N1—C2	108.3 (3)	C8—C9—H9	120.2
N2—N1—C1	127.3 (3)	C9—C10—O1	124.5 (3)
C2—N1—C1	124.4 (3)	C9—C10—C11	120.1 (3)
N3—N2—N1	105.4 (3)	O1—C10—C11	115.4 (3)
N2—N3—N4	112.9 (3)	C12—C11—C10	119.1 (3)
C2—N4—N3	105.6 (3)	C12—C11—H11	120.4
C1—N5—C4	114.9 (3)	C10—C11—H11	120.4
C4—N6—C5	107.7 (3)	C11—C12—C7	122.1 (3)
C4—N6—C14	128.4 (3)	C11—C12—H12	118.9
C5—N6—C14	123.8 (3)	C7—C12—H12	118.9
N5—C1—N1	122.0 (3)	O1—C13—H13A	109.5
N5—C1—H1	119.0	O1—C13—H13B	109.5
N1—C1—H1	119.0	H13A—C13—H13B	109.5
N4—C2—N1	107.9 (3)	O1—C13—H13C	109.5
N4—C2—C3	135.6 (3)	H13A—C13—H13C	109.5
N1—C2—C3	116.5 (3)	H13B—C13—H13C	109.5
C4—C3—C2	113.9 (3)	C15—C14—C19	120.8 (3)
C4—C3—C6	108.2 (3)	C15—C14—N6	120.0 (3)
C2—C3—C6	137.8 (3)	C19—C14—N6	119.2 (3)
N5—C4—N6	123.7 (3)	C14—C15—C16	118.8 (4)
N5—C4—C3	128.3 (3)	C14—C15—H15	120.6
N6—C4—C3	107.9 (3)	C16—C15—H15	120.6
C6—C5—N6	111.2 (3)	C17—C16—C15	120.7 (4)
C6—C5—H5	124.4	C17—C16—H16	119.6
N6—C5—H5	124.4	C15—C16—H16	119.6
C5—C6—C3	104.9 (3)	C16—C17—C18	119.1 (3)
C5—C6—C7	124.2 (3)	C16—C17—H17	120.4
C3—C6—C7	130.9 (3)	C18—C17—H17	120.4
C12—C7—C8	117.6 (3)	C19—C18—C17	121.1 (4)
C12—C7—C6	120.0 (3)	C19—C18—H18	119.5
C8—C7—C6	122.4 (3)	C17—C18—H18	119.5
C7—C8—C9	121.4 (3)	C18—C19—C14	119.4 (4)
C7—C8—H8	119.3	C18—C19—H19	120.3
C9—C8—H8	119.3	C14—C19—H19	120.3
C10—C9—C8	119.6 (3)
C2—N1—N2—N3	−0.4 (7)	C2—C3—C6—C5	−177.7 (6)
C1—N1—N2—N3	179.5 (5)	C4—C3—C6—C7	−179.5 (5)
N1—N2—N3—N4	0.5 (8)	C2—C3—C6—C7	3.6 (11)
N2—N3—N4—C2	−0.5 (7)	C5—C6—C7—C12	23.8 (8)
C4—N5—C1—N1	0.3 (7)	C3—C6—C7—C12	−157.7 (5)
N2—N1—C1—N5	179.6 (5)	C5—C6—C7—C8	−154.3 (5)
C2—N1—C1—N5	−0.5 (8)	C3—C6—C7—C8	24.2 (9)
N3—N4—C2—N1	0.2 (6)	C12—C7—C8—C9	−2.1 (7)
N3—N4—C2—C3	−179.7 (7)	C6—C7—C8—C9	176.0 (4)
N2—N1—C2—N4	0.1 (6)	C7—C8—C9—C10	0.8 (7)
C1—N1—C2—N4	−179.8 (5)	C8—C9—C10—O1	−178.6 (4)
N2—N1—C2—C3	−179.9 (5)	C8—C9—C10—C11	1.3 (7)
C1—N1—C2—C3	0.2 (8)	C13—O1—C10—C9	8.3 (6)
N4—C2—C3—C4	−179.7 (6)	C13—O1—C10—C11	−171.7 (4)
N1—C2—C3—C4	0.3 (7)	C9—C10—C11—C12	−2.1 (7)
N4—C2—C3—C6	−2.9 (12)	O1—C10—C11—C12	177.8 (4)
N1—C2—C3—C6	177.1 (6)	C10—C11—C12—C7	0.8 (7)
C1—N5—C4—N6	−178.8 (5)	C8—C7—C12—C11	1.3 (7)
C1—N5—C4—C3	0.2 (8)	C6—C7—C12—C11	−176.9 (4)
C5—N6—C4—N5	178.6 (5)	C4—N6—C14—C15	−39.1 (7)
C14—N6—C4—N5	2.3 (8)	C5—N6—C14—C15	145.1 (4)
C5—N6—C4—C3	−0.6 (5)	C4—N6—C14—C19	142.5 (5)
C14—N6—C4—C3	−176.9 (5)	C5—N6—C14—C19	−33.3 (7)
C2—C3—C4—N5	−0.6 (8)	C19—C14—C15—C16	−2.3 (6)
C6—C3—C4—N5	−178.3 (5)	N6—C14—C15—C16	179.3 (4)
C2—C3—C4—N6	178.6 (4)	C14—C15—C16—C17	2.3 (7)
C6—C3—C4—N6	0.9 (6)	C15—C16—C17—C18	−0.5 (7)
C4—N6—C5—C6	0.1 (5)	C16—C17—C18—C19	−1.4 (7)
C14—N6—C5—C6	176.6 (5)	C17—C18—C19—C14	1.4 (7)
N6—C5—C6—C3	0.4 (6)	C15—C14—C19—C18	0.5 (7)
N6—C5—C6—C7	179.2 (5)	N6—C14—C19—C18	178.8 (4)
C4—C3—C6—C5	−0.8 (6)

Cg1 is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N4	0.93	2.50	3.257 (5)	138
C15—H15···N5	0.93	2.57	3.020 (5)	111
C11—H11···Cg1i	0.93	2.91	3.684 (5)	141
C13—H13c···Cg1ii	0.96	2.72	3.459 (5)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯N4	0.93	2.50	3.257 (5)	138
C15—H15⋯N5	0.93	2.57	3.020 (5)	111
C11—H11⋯Cg1i	0.93	2.91	3.684 (5)	141
C13—H13c⋯Cg1ii	0.96	2.72	3.459 (5)	134

Symmetry codes: (i) ; (ii) .