7-(4-Methoxy­phen­yl)-5-methyl-9-phenyl-7H-pyrrolo[2′,3′:4,5]pyrimido[1,6-d]tetrazole

Jotani, M.M.; Shah, R.D.; Jasinski, J.P.

doi:10.1107/S1600536809053653

7-(4-Methoxyphenyl)-5-methyl-9-phenyl-7H-pyrrolo[2′,3′:4,5]pyrimido[1,6-d]tetrazole

M. M. Jotani, R. D. Shah and J. P. Jasinski

The title compound, C₂₀H₁₆N₆O, is composed of a tetrazolo ring and a 4-methoxyphenyl and a benzene-substituted pyrrole ring at the 7 and 9 positions fused to a pyrimidine ring in a nearly planar fashion [maximum deviation of 0.018 (1) Å for the fused ring system]. A methyl group at the 5 position is also in the plane of the hetero cyclic system. The dihedral angle between the mean planes of the benzene and 4-methoxyphenyl rings is 40.4 (2)°. The dihedral angles between the mean planes of the pyrimidine and the benzene and 4-methoxyphenyl rings are 15.6 (5)° and 52.6 (7)°, respectively. A weak intramolecular C—H

N hydrogen bond interaction, which forms an S(7) graph-set motif, helps to establish the relative conformations of the tetrazolo and benzene rings. In the crystal, weak intermolecular C—H

O, C—H

π and π–π stacking interactions [centroid–centroid distances = 3.5270 (16), 3.5113 (16), 3.7275 (17) and 3.7866 (17) Å] link the molecules into a two-dimensional array obliquely parallel to (101) and propagating along the b axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809053653/gw2072sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809053653/gw2072Isup2.hkl Contains datablock I

CCDC reference: 723856

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.045
wR factor = 0.129
Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found





Alert level A
PLAT900_ALERT_1_A No Matching Reflection File Found ..............          !
PLAT900_ALERT_1_A No Matching Reflection File Found ..............          !
PLAT902_ALERT_1_A No (Interpretable) Reflections found in FCF ....          !

Alert level C
PLAT725_ALERT_2_C D-H     Calc     0.98000, Rep     0.96000 Dev...       0.02 Ang.
              C7   -H7B     1.555   1.555
PLAT725_ALERT_2_C D-H     Calc     0.98000, Rep     0.96000 Dev...       0.02 Ang.
              C7   -H7C     1.555   1.555

Alert level G
PLAT128_ALERT_4_G Non-standard setting of Space-group P21/c   ....      P21/n
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K

   3 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Fused tetrazolopyrimidines are important to the activities of a variety of biological substances (Willkinson, 1992; Omer et al., 1991; Schram et al., 1975). Moreover, fused pyrimidines having a halogen at the 2- or 4- position seem to be more labile towards a nucleophilic substitution reaction with reagents such as piperadine, piperazine, morpholine, hydrazine and azides to form potent bi and triheterocycles (Dave & Shah, 2002; Peinador et al., 1992; Schneller & Clough, 1992; Shishoo & Jain, 1992). The reduction of tetrazolopyrimidines via azidolysis studies have been shown to be to attractive to development of synthetically important 4-aminopyrimidines (Shishoo & Jain, 1992; Hand & Backer, 1984). The treatment of sodium azide with 4-chloropyrrolo[2,3-e] pyrimidine can result the formation of either an azido group or tetrazole ring upon a fused pyrimidine ring. Such nucleophilic substitution reactions have rarely been attempted in pyrrolo[2,3-e] pyrimidines (Dave & Shah, 2002; Ali & Swealan, 1992). In view of the importance of these molecules, a crystal structure of the title compound, C₂₀H₁₆N₆O, (I) has been determined.

The title compound, C₂₀H₁₆N₆O, (I), is composed of a tetrazolo ring and a 4-methoxyphenyl and benzene substituted pyrrole ring at the 7 and 9 position fused to a pyrimidine ring in a nearly planar fashion (Fig. 1). The r.m.s.deviation of atoms of the fused ring from the mean plane through the heterotricyclic system is 0.0085 Å, with a maximum deviation of -0.018 (1) and 0.013 (1) Å for atoms C2 and C3 respectively. Bond lengths and angles for the fused pyrrole and tetrazole rings in (I) are normal and similar to that observed for a related structure. The dihedral angles between the mean planes of fused pyrimidine and tetrazole rings with that of the pyrrole ring are 1.26 (6) ° and 1.13 (7)°, respectively. A methyl group at the 5 position is also in the plane of the pyrimidine ring. The dihedral angle between the mean planes of the benzene and 4-methoxyphenyl rings is 40.4 (2)°. The angles between the mean planes of the pyrimidine and the benzene and 4-methoxyphenyl rings are 15.6 (5)° and 52.6 (7)°, respectively. A weak intramolecular C13–H13···N6 hydrogen bond interaction, which forms an S(7) graph set, helps stabilize the separation angle between the tetrazolo and benzene rings. Weak intermolecular C12–H12···O1 (Fig. 2), C–H···π-ring (C7–H7B(H7C)···Cg4 [= 3.620 (2) (3.554 (2) Å; 1 - x, 1 - y, 1 - z (1 - x, 2 - y, 1 - z); where Cg4 = C8–C13 ring centroid; Table 1] and π–π [Cg1···Cg2; = 3.5270 (16)Å & 3.5113 (16) Å,1 - x, 1 - y, 1 - x & 1 - x, 2 - y, 1 - z; Cg2···Cg3; = 3.7275 (17) Å, 1 - x, 2 - y, 1 - z; Cg3···Cg1; = 3.7866 (17) Å, 1 - x, 1 - y, 1 - z; where Cg1 = N1/C1–C4, Cg2 = N3–N6/C6, Cg3 = N2/C1–C5] stacking interactions (Fig. 3) help to link the molecules into a 2-D array obliquely parallel to (101) and propagating along the b axis.

Related literature top

For the biological activity of fused tetrazolopyrimidines, see: Wilkinson (1992); Omer et al. (1991); Schram et al. (1975). Fused pyrimidines with a halogen at the 2- or 4- position seem to be more labile towards a nucleophilic substitution reaction with reagents such as piperadine, piperazine, morpholine, hydrazine and azides, forming potent bi and triheterocycles, see: Dave & Shah (2000, 2002); Peinador et al. (1992); Schneller & Clough (1992); Shishoo & Jain (1992). For the importance of the reduction of tetrazolopyrimidines via azidolysis in the development of synthetically important 4-aminopyrimidines, see: Shishoo & Jain (1992); Hand & Backer (1984). For nucleophilic substitution reactions in pyrrolo[2,3-e] pyrimidines, see: Dave & Shah (2002); Ali & Swealan (1992). For related structures, see: Jotani & Baldaniya (2007, 2008); Hou et al. (2009); Baldaniya & Jotani (2008); Malone et al. (1997). For the synthesis, see: Shah (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For tetrazolo ring formation, see: Bourgurgnon et al. (1975); Robba et al. (1975).

Experimental top

The title compound was synthesized according to method of Shah (2009). A mixture of sodium azide (0.011 mole), ammonium chloride (0.011 mole) and 2-methyl-5-phenyl-7-(4-methoxyphenyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.01 mole) in DMSO (20 ml) was stirred for for 2 h at 363 K to obtain the title compound (I). Colorless platlike single crystals, suitable for X-ray diffraction were grown from a solution of 1,4-dioxane.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR2004 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-32 and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom labelling scheme and 50% probability displacement ellipsoids. The dashed line represents a weak intramolecular C–H···N hydrogen bond interaction.
	Fig. 2. Crystal packing of (I), showing weak intramolecular C–H···N and intermolecular C–H···O hydrogen bond interactions as dashed lines.
	Fig. 3. The molecular packing of (I), showing π–π stacking interactions as dashed lines forming chains of molecules along [1 0 1] plane if the unit cell.

7-(4-Methoxyphenyl)-5-methyl-9-phenyl-7H- pyrrolo[2',3':4,5]pyrimido[1,6-d]tetrazole top

Crystal data top

C₂₀H₁₆N₆O	F(000) = 744
M_r = 356.39	D_x = 1.344 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5176 reflections
a = 13.738 (2) Å	θ = 2.2–31.3°
b = 7.032 (3) Å	µ = 0.09 mm⁻¹
c = 19.4350 (3) Å	T = 293 K
β = 110.217 (2)°	Plate, yellow
V = 1761.9 (8) Å³	0.47 × 0.35 × 0.2 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	5137 independent reflections
Radiation source: fine-focus sealed tube	3694 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scan	θ_max = 30.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −19→19
T_min = 0.96, T_max = 0.98	k = −4→9
42323 measured reflections	l = −27→27

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0656P)² + 0.2469P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
5137 reflections	Δρ_max = 0.29 e Å⁻³
247 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0104 (12)

Crystal data top

C₂₀H₁₆N₆O	V = 1761.9 (8) Å³
M_r = 356.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.738 (2) Å	µ = 0.09 mm⁻¹
b = 7.032 (3) Å	T = 293 K
c = 19.4350 (3) Å	0.47 × 0.35 × 0.2 mm
β = 110.217 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5137 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3694 reflections with I > 2σ(I)
T_min = 0.96, T_max = 0.98	R_int = 0.030
42323 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.04	Δρ_max = 0.29 e Å⁻³
5137 reflections	Δρ_min = −0.20 e Å⁻³
247 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.49323 (7)	0.66669 (14)	0.35550 (5)	0.0364 (2)
N2	0.64444 (8)	0.71967 (13)	0.46114 (6)	0.0390 (2)
N3	0.60830 (8)	0.78499 (13)	0.56626 (5)	0.0387 (2)
N4	0.63253 (10)	0.82763 (16)	0.63905 (6)	0.0503 (3)
N5	0.54477 (10)	0.84057 (18)	0.64892 (6)	0.0553 (3)
N6	0.46241 (9)	0.80796 (15)	0.58676 (5)	0.0461 (3)
O1	0.67511 (8)	0.63011 (14)	0.14173 (5)	0.0557 (3)
C1	0.54006 (9)	0.70521 (14)	0.42843 (6)	0.0342 (2)
C2	0.46308 (9)	0.72839 (14)	0.45931 (6)	0.0322 (2)
C3	0.36448 (9)	0.70460 (14)	0.40206 (6)	0.0331 (2)
C4	0.38831 (9)	0.66682 (16)	0.34039 (6)	0.0372 (2)
H4	0.3383	0.6437	0.2933	0.045*
C5	0.67850 (10)	0.75945 (15)	0.53047 (7)	0.0400 (3)
C6	0.50261 (9)	0.77276 (14)	0.53513 (6)	0.0350 (2)
C7	0.79065 (11)	0.7757 (2)	0.57366 (8)	0.0538 (3)
H7A	0.8307	0.7651	0.5408	0.081*
H7B	0.8109	0.6735	0.6102	0.081*
H7C	0.8044	0.8991	0.5986	0.081*
C8	0.25890 (9)	0.71760 (15)	0.40362 (6)	0.0348 (2)
C9	0.17475 (10)	0.73306 (18)	0.33836 (7)	0.0437 (3)
H9	0.1867	0.7361	0.2931	0.052*
C10	0.07452 (11)	0.7441 (2)	0.33822 (8)	0.0531 (3)
H10	0.0183	0.7540	0.2931	0.064*
C11	0.05569 (11)	0.7407 (2)	0.40303 (9)	0.0572 (4)
H11	−0.0134	0.7493	0.4030	0.069*
C12	0.13717 (12)	0.7249 (2)	0.46801 (9)	0.0559 (4)
H12	0.1242	0.7217	0.5129	0.067*
C13	0.23768 (11)	0.71372 (18)	0.46865 (7)	0.0444 (3)
H13	0.2932	0.7032	0.5141	0.053*
C14	0.54240 (9)	0.65119 (16)	0.30183 (6)	0.0352 (2)
C15	0.50818 (9)	0.76648 (17)	0.24049 (6)	0.0409 (3)
H15	0.4533	0.8542	0.2348	0.049*
C16	0.55355 (10)	0.75407 (18)	0.18782 (7)	0.0437 (3)
H16	0.5294	0.8320	0.1454	0.052*
C17	0.63448 (9)	0.62818 (17)	0.19641 (6)	0.0397 (3)
C18	0.66942 (9)	0.51457 (18)	0.25825 (7)	0.0430 (3)
H18	0.7254	0.4291	0.2646	0.052*
C19	0.62275 (9)	0.52564 (17)	0.31077 (6)	0.0413 (3)
H19	0.6461	0.4467	0.3530	0.050*
C20	0.75810 (14)	0.5043 (3)	0.14708 (10)	0.0782 (6)
H20A	0.8168	0.5324	0.1918	0.117*
H20B	0.7795	0.5207	0.1043	0.117*
H20C	0.7354	0.3728	0.1488	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0378 (5)	0.0443 (5)	0.0276 (5)	0.0018 (4)	0.0121 (4)	−0.0010 (4)
N2	0.0382 (5)	0.0396 (5)	0.0362 (5)	0.0018 (4)	0.0092 (4)	0.0011 (4)
N3	0.0492 (6)	0.0345 (4)	0.0271 (5)	−0.0023 (4)	0.0064 (4)	0.0001 (3)
N4	0.0663 (8)	0.0509 (6)	0.0272 (5)	−0.0076 (5)	0.0080 (5)	−0.0035 (4)
N5	0.0717 (8)	0.0613 (7)	0.0300 (6)	−0.0110 (6)	0.0139 (5)	−0.0068 (5)
N6	0.0620 (7)	0.0495 (6)	0.0284 (5)	−0.0074 (5)	0.0175 (5)	−0.0042 (4)
O1	0.0641 (6)	0.0690 (6)	0.0459 (5)	0.0180 (5)	0.0340 (5)	0.0111 (4)
C1	0.0401 (6)	0.0329 (5)	0.0285 (5)	0.0015 (4)	0.0105 (4)	0.0016 (4)
C2	0.0406 (6)	0.0288 (4)	0.0272 (5)	0.0002 (4)	0.0118 (4)	0.0018 (4)
C3	0.0388 (6)	0.0327 (5)	0.0278 (5)	0.0006 (4)	0.0115 (4)	0.0016 (4)
C4	0.0365 (6)	0.0436 (6)	0.0298 (5)	0.0000 (4)	0.0095 (5)	−0.0017 (4)
C5	0.0437 (7)	0.0334 (5)	0.0373 (6)	0.0010 (4)	0.0069 (5)	0.0014 (4)
C6	0.0458 (6)	0.0289 (5)	0.0293 (5)	−0.0020 (4)	0.0115 (5)	0.0017 (4)
C7	0.0451 (7)	0.0510 (7)	0.0520 (8)	−0.0023 (5)	−0.0001 (6)	−0.0040 (6)
C8	0.0407 (6)	0.0320 (5)	0.0326 (6)	−0.0005 (4)	0.0137 (5)	−0.0007 (4)
C9	0.0426 (7)	0.0532 (7)	0.0346 (6)	0.0003 (5)	0.0124 (5)	−0.0012 (5)
C10	0.0404 (7)	0.0647 (8)	0.0496 (8)	0.0015 (6)	0.0096 (6)	−0.0037 (6)
C11	0.0430 (8)	0.0684 (9)	0.0646 (10)	−0.0028 (6)	0.0244 (7)	−0.0089 (7)
C12	0.0543 (8)	0.0711 (9)	0.0512 (8)	−0.0043 (7)	0.0297 (7)	−0.0068 (6)
C13	0.0464 (7)	0.0536 (7)	0.0349 (6)	−0.0008 (5)	0.0161 (5)	−0.0016 (5)
C14	0.0369 (6)	0.0420 (5)	0.0277 (5)	−0.0006 (4)	0.0124 (4)	−0.0023 (4)
C15	0.0381 (6)	0.0512 (6)	0.0327 (6)	0.0103 (5)	0.0113 (5)	0.0035 (5)
C16	0.0448 (7)	0.0550 (7)	0.0312 (6)	0.0087 (5)	0.0129 (5)	0.0090 (5)
C17	0.0416 (6)	0.0474 (6)	0.0337 (6)	0.0020 (5)	0.0174 (5)	0.0000 (4)
C18	0.0451 (7)	0.0448 (6)	0.0426 (7)	0.0110 (5)	0.0195 (5)	0.0049 (5)
C19	0.0472 (7)	0.0433 (6)	0.0348 (6)	0.0075 (5)	0.0158 (5)	0.0069 (4)
C20	0.0943 (13)	0.0825 (11)	0.0864 (12)	0.0367 (10)	0.0674 (11)	0.0245 (9)

Geometric parameters (Å, º) top

N1—C1	1.3661 (14)	C8—C9	1.3942 (17)
N1—C4	1.3680 (15)	C9—C10	1.3783 (18)
N1—C14	1.4294 (14)	C9—H9	0.9500
N2—C5	1.2951 (16)	C10—C11	1.371 (2)
N2—C1	1.3567 (15)	C10—H10	0.9500
N3—C6	1.3691 (16)	C11—C12	1.372 (2)
N3—N4	1.3699 (14)	C11—H11	0.9500
N3—C5	1.3819 (17)	C12—C13	1.379 (2)
N4—N5	1.2879 (17)	C12—H12	0.9500
N5—N6	1.3591 (16)	C13—H13	0.9500
N6—C6	1.3254 (15)	C14—C19	1.3768 (16)
O1—C17	1.3606 (13)	C14—C15	1.3828 (16)
O1—C20	1.4183 (17)	C15—C16	1.3730 (17)
C1—C2	1.3942 (16)	C15—H15	0.9500
C2—C6	1.4178 (15)	C16—C17	1.3854 (17)
C2—C3	1.4351 (15)	C16—H16	0.9500
C3—C4	1.3730 (15)	C17—C18	1.3835 (16)
C3—C8	1.4640 (16)	C18—C19	1.3825 (16)
C4—H4	0.9500	C18—H18	0.9500
C5—C7	1.4824 (18)	C19—H19	0.9500
C7—H7A	0.9800	C20—H20A	0.9800
C7—H7B	0.9800	C20—H20B	0.9800
C7—H7C	0.9800	C20—H20C	0.9800
C8—C13	1.3920 (17)

C1—N1—C4	107.82 (9)	C10—C9—H9	119.3
C1—N1—C14	126.90 (10)	C8—C9—H9	119.3
C4—N1—C14	124.89 (9)	C11—C10—C9	120.20 (14)
C5—N2—C1	116.55 (11)	C11—C10—H10	119.9
C6—N3—N4	108.19 (10)	C9—C10—H10	119.9
C6—N3—C5	125.97 (10)	C10—C11—C12	119.60 (13)
N4—N3—C5	125.83 (11)	C10—C11—H11	120.2
N5—N4—N3	105.27 (10)	C12—C11—H11	120.2
N4—N5—N6	112.98 (11)	C11—C12—C13	120.58 (13)
C6—N6—N5	105.53 (11)	C11—C12—H12	119.7
C17—O1—C20	118.22 (10)	C13—C12—H12	119.7
N2—C1—N1	122.92 (10)	C12—C13—C8	120.93 (13)
N2—C1—C2	128.74 (10)	C12—C13—H13	119.5
N1—C1—C2	108.33 (10)	C8—C13—H13	119.5
C1—C2—C6	113.45 (10)	C19—C14—C15	120.24 (10)
C1—C2—C3	107.80 (9)	C19—C14—N1	121.15 (10)
C6—C2—C3	138.71 (11)	C15—C14—N1	118.61 (10)
C4—C3—C2	104.68 (10)	C16—C15—C14	119.92 (11)
C4—C3—C8	124.54 (10)	C16—C15—H15	120.0
C2—C3—C8	130.77 (10)	C14—C15—H15	120.0
N1—C4—C3	111.35 (10)	C15—C16—C17	120.19 (11)
N1—C4—H4	124.3	C15—C16—H16	119.9
C3—C4—H4	124.3	C17—C16—H16	119.9
N2—C5—N3	119.19 (11)	O1—C17—C18	124.85 (11)
N2—C5—C7	122.47 (12)	O1—C17—C16	115.35 (10)
N3—C5—C7	118.33 (11)	C18—C17—C16	119.78 (11)
N6—C6—N3	108.03 (10)	C19—C18—C17	119.91 (11)
N6—C6—C2	135.87 (11)	C19—C18—H18	120.0
N3—C6—C2	116.10 (10)	C17—C18—H18	120.0
C5—C7—H7A	109.5	C14—C19—C18	119.94 (11)
C5—C7—H7B	109.5	C14—C19—H19	120.0
H7A—C7—H7B	109.5	C18—C19—H19	120.0
C5—C7—H7C	109.5	O1—C20—H20A	109.5
H7A—C7—H7C	109.5	O1—C20—H20B	109.5
H7B—C7—H7C	109.5	H20A—C20—H20B	109.5
C13—C8—C9	117.35 (11)	O1—C20—H20C	109.5
C13—C8—C3	122.51 (11)	H20A—C20—H20C	109.5
C9—C8—C3	120.13 (10)	H20B—C20—H20C	109.5
C10—C9—C8	121.33 (12)

C6—N3—N4—N5	−0.45 (12)	C5—N3—C6—C2	0.47 (15)
C5—N3—N4—N5	179.34 (10)	C1—C2—C6—N6	179.44 (12)
N3—N4—N5—N6	0.33 (14)	C3—C2—C6—N6	1.9 (2)
N4—N5—N6—C6	−0.08 (14)	C1—C2—C6—N3	−0.34 (13)
C5—N2—C1—N1	179.05 (10)	C3—C2—C6—N3	−177.88 (11)
C5—N2—C1—C2	0.35 (17)	C4—C3—C8—C13	165.29 (11)
C4—N1—C1—N2	−178.52 (10)	C2—C3—C8—C13	−15.64 (17)
C14—N1—C1—N2	−5.42 (17)	C4—C3—C8—C9	−14.18 (16)
C4—N1—C1—C2	0.41 (12)	C2—C3—C8—C9	164.89 (11)
C14—N1—C1—C2	173.51 (10)	C13—C8—C9—C10	0.00 (17)
N2—C1—C2—C6	−0.04 (16)	C3—C8—C9—C10	179.50 (11)
N1—C1—C2—C6	−178.89 (9)	C8—C9—C10—C11	0.3 (2)
N2—C1—C2—C3	178.25 (10)	C9—C10—C11—C12	−0.5 (2)
N1—C1—C2—C3	−0.60 (11)	C10—C11—C12—C13	0.4 (2)
C1—C2—C3—C4	0.54 (11)	C11—C12—C13—C8	−0.2 (2)
C6—C2—C3—C4	178.17 (12)	C9—C8—C13—C12	−0.05 (17)
C1—C2—C3—C8	−178.67 (10)	C3—C8—C13—C12	−179.54 (11)
C6—C2—C3—C8	−1.0 (2)	C1—N1—C14—C19	55.88 (16)
C1—N1—C4—C3	−0.06 (13)	C4—N1—C14—C19	−132.14 (12)
C14—N1—C4—C3	−173.33 (10)	C1—N1—C14—C15	−123.61 (12)
C2—C3—C4—N1	−0.30 (12)	C4—N1—C14—C15	48.36 (16)
C8—C3—C4—N1	178.97 (9)	C19—C14—C15—C16	0.85 (18)
C1—N2—C5—N3	−0.24 (15)	N1—C14—C15—C16	−179.66 (11)
C1—N2—C5—C7	178.70 (10)	C14—C15—C16—C17	−0.88 (19)
C6—N3—C5—N2	−0.17 (16)	C20—O1—C17—C18	1.4 (2)
N4—N3—C5—N2	−179.92 (10)	C20—O1—C17—C16	−179.88 (14)
C6—N3—C5—C7	−179.15 (10)	C15—C16—C17—O1	−178.74 (12)
N4—N3—C5—C7	1.10 (16)	C15—C16—C17—C18	0.1 (2)
N5—N6—C6—N3	−0.22 (12)	O1—C17—C18—C19	179.42 (12)
N5—N6—C6—C2	179.99 (12)	C16—C17—C18—C19	0.70 (19)
N4—N3—C6—N6	0.42 (12)	C15—C14—C19—C18	−0.04 (18)
C5—N3—C6—N6	−179.37 (10)	N1—C14—C19—C18	−179.52 (11)
N4—N3—C6—C2	−179.74 (9)	C17—C18—C19—C14	−0.73 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N6	0.95	2.38	3.2159 (18)	146
C12—H12···O1ⁱ	0.95	2.57	3.3902 (17)	144
C7—H7B···Cg4ⁱⁱ	0.96	2.90	3.620 (2)	132
C7—H7C···Cg4ⁱⁱⁱ	0.96	2.69	3.554 (2)	150

Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₆O
M_r	356.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.738 (2), 7.032 (3), 19.4350 (3)
β (°)	110.217 (2)
V (Å³)	1761.9 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.47 × 0.35 × 0.2

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.96, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	42323, 5137, 3694
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.129, 1.04
No. of reflections	5137
No. of parameters	247
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.20

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR2004 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-32 and PLATON (Spek, 2009).