5,5-Dimethyl-2-phenyl-4,5-dihydro-1,2,4-triazolo[1,5-a][1,3,5]triazin-7-amine

Dolzhenko, A.V.; Tan, G.K.; Koh, L.L.; Dolzhenko, A.V.; Chui, W.K.

doi:10.1107/S1600536807021022

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5,5-Dimethyl-2-phenyl-4,5-dihydro-1,2,4-triazolo[1,5-a][1,3,5]triazin-7-amine

A. V. Dolzhenko, G. K. Tan, L. L. Koh, A. V. Dolzhenko and W. K. Chui

The title compound, C₁₂H₁₄N₆, was synthesized via cyclocondensation of 5-amino-1-guanyl-3-phenyl-1,2,4-triazole with acetone. Only one tautomeric form with an H atom at the triazine N atom was observed in the crystal structure. The compound crystallizes with two almost identical molecules in the asymmetric unit. In both molecules, the triazine ring adopts a conformation intermediate between a twist–boat and a half-boat. The crystal packing is stabilized by intermolecular N—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021022/ci2380sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021022/ci2380Isup2.hkl Contains datablock I

CCDC reference: 651375

checkCIF report

Key indicators

Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.002 Å
R factor = 0.046
wR factor = 0.121
Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT420_ALERT_2_C D-H Without Acceptor       N11    -   H11N   ...          ?

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

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

Comment top

1,2,4-triazolo[1,5-a][1,3,5]triazines (5-azapurines) have been shown to exhibit many types of important biological activities (Dolzhenko et al., 2006). As a part of our ongoing investigation on the derivatives of this heterocyclic system (Dolzhenko, Dolzhenko & Chui, 2007), we report herein the crystallographic study of the title compound (I) which is a regioisomer of previously described 7,7-dimethyl-2-phenyl-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin- 5-amine (Dolzhenko, Tan et al., 2007).

The title compound (I), C₁₂H₁₄N₆, was prepared by cyclocondensation of 5-amino-1-guanyl-3-phenyl-1,2,4-triazole with acetone. In general, the synthesized compound might be involved in annular tautomerism with three possible tautomeric forms (Fig. 1). However, only one tautomeric form viz. 5,5-dimethyl-2-phenyl-4,5-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin- 7-amine (I) was observed in the crystal.

Compound (I) crystallizes with two independent molecules, A (Fig. 2) and B (Fig. 3), in the asymmetric unit (Fig. 4). The triazine rings of the molecules A and B adopt similar conformations best described as an intermediate between a twist-boat and a half-boat with atom C10 (C22) at the bow. The mean planes of the triazole and phenyl rings make a dihedral angles of 11.30 (5)° and 8.40 (6)° for the molecules A and B, respectively. The crystal packing is stabilized by intermolecular N—H···N hydrogen-bonds (Table 1)

Related literature top

The 1,2,4-triazolo[1,5-a][1,3,5]triazine (5-azapurine) heterocyclic system has been reviewed by Dolzhenko et al. (2006). The crystal structure of 7,7-dimethyl-2-phenyl-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin- 5-amine, which is regioisomeric with the title compound, (I), is reported in the previous paper (Dolzhenko, Tan et al., 2007). For related literature, see also Dolzhenko, Dolzhenko & Chui (2007).

Experimental top

5-Amino-1-guanyl-3-phenyl-1,2,4-triazole (0.50 g, 2.5 mmol) was heated under reflux in acetone (8 ml) containing piperidine (0.05 ml, 0.5 mmol) for 12 h. After cooling, the precipitated solid was filtered, washed with acetone and recrystallized from ethanol (m.p. 482 K).

Structure description top

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The annular tautomerism in (I).
	Fig. 2. One of the independent molecules of (I), molecule A, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 3. One of the independent molecules of (I), molecule B, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 4. The asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level.

5,5-Dimethyl-2-phenyl-4,5-dihydro-1,2,4-triazolo[1,5-a][1,3,5]triazin-\7-amine top

Crystal data top

C₁₂H₁₄N₆	Z = 4
M_r = 242.29	F(000) = 512
Triclinic, P1	D_x = 1.331 Mg m⁻³
Hall symbol: -P 1	Melting point: 482 K
a = 9.7224 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.9752 (6) Å	Cell parameters from 4987 reflections
c = 12.4432 (6) Å	θ = 2.3–27.4°
α = 112.200 (1)°	µ = 0.09 mm⁻¹
β = 103.737 (1)°	T = 223 K
γ = 104.161 (1)°	Block, colourless
V = 1209.58 (10) Å³	0.40 × 0.38 × 0.20 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5549 independent reflections
Radiation source: fine-focus sealed tube, Bruker SMART APEX CCD area-detector	4621 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −12→12
T_min = 0.931, T_max = 0.980	k = −15→15
15995 measured reflections	l = −16→16

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0629P)² + 0.25P] where P = (F_o² + 2F_c²)/3
5549 reflections	(Δ/σ)_max = 0.001
337 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₂H₁₄N₆	γ = 104.161 (1)°
M_r = 242.29	V = 1209.58 (10) Å³
Triclinic, P1	Z = 4
a = 9.7224 (5) Å	Mo Kα radiation
b = 11.9752 (6) Å	µ = 0.09 mm⁻¹
c = 12.4432 (6) Å	T = 223 K
α = 112.200 (1)°	0.40 × 0.38 × 0.20 mm
β = 103.737 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5549 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	4621 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.980	R_int = 0.026
15995 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.30 e Å⁻³
5549 reflections	Δρ_min = −0.29 e Å⁻³
337 parameters

Special details top

Experimental. The su's on the cell Angles are rounded values.

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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.43352 (12)	0.53590 (11)	0.34655 (11)	0.0283 (3)
N2	0.49145 (12)	0.35638 (10)	0.32551 (10)	0.0257 (2)
N3	0.62201 (12)	0.46598 (10)	0.37342 (10)	0.0254 (2)
N4	0.88222 (12)	0.58752 (11)	0.46028 (11)	0.0270 (2)
N5	0.69510 (13)	0.68668 (11)	0.43546 (12)	0.0316 (3)
H5N	0.6728 (19)	0.7549 (16)	0.4426 (15)	0.037 (4)*
N6	0.79574 (13)	0.37717 (11)	0.43315 (12)	0.0331 (3)
H6A	0.8877	0.3806	0.4644	0.040*
H6B	0.7177	0.3068	0.4073	0.040*
C1	0.11373 (16)	0.38462 (14)	0.25729 (13)	0.0317 (3)
H1	0.1475	0.4758	0.2972	0.038*
C2	−0.04123 (17)	0.31081 (16)	0.20182 (14)	0.0381 (3)
H2	−0.1120	0.3521	0.2045	0.046*
C3	−0.09205 (17)	0.17701 (16)	0.14279 (14)	0.0409 (4)
H3	−0.1972	0.1270	0.1044	0.049*
C4	0.01239 (18)	0.11703 (15)	0.14052 (15)	0.0406 (4)
H4	−0.0222	0.0258	0.1007	0.049*
C5	0.16773 (16)	0.18946 (14)	0.19612 (14)	0.0336 (3)
H5	0.2377	0.1474	0.1945	0.040*
C6	0.21989 (14)	0.32455 (13)	0.25427 (12)	0.0261 (3)
C7	0.38395 (14)	0.40484 (12)	0.31078 (12)	0.0248 (3)
C8	0.58319 (15)	0.57033 (12)	0.38609 (12)	0.0257 (3)
C9	0.77452 (14)	0.48004 (12)	0.42477 (12)	0.0244 (3)
C10	0.84763 (14)	0.68883 (13)	0.43383 (13)	0.0264 (3)
C11	0.85505 (18)	0.66838 (16)	0.30710 (14)	0.0391 (4)
H11A	0.9524	0.6628	0.3052	0.059*
H11B	0.8443	0.7409	0.2934	0.059*
H11C	0.7731	0.5884	0.2421	0.059*
C12	0.96425 (16)	0.82034 (14)	0.53578 (14)	0.0345 (3)
H12A	0.9585	0.8319	0.6159	0.052*
H12B	0.9430	0.8885	0.5191	0.052*
H12C	1.0657	0.8246	0.5374	0.052*
N7	0.64515 (12)	0.91698 (10)	0.41712 (10)	0.0253 (2)
N8	0.62672 (13)	1.09681 (10)	0.40021 (10)	0.0257 (2)
N9	0.58770 (13)	0.99346 (10)	0.28465 (10)	0.0257 (2)
N10	0.51588 (14)	0.88737 (11)	0.06878 (10)	0.0311 (3)
N11	0.55846 (14)	0.77685 (11)	0.19483 (11)	0.0289 (3)
H11N	0.562 (2)	0.7133 (19)	0.2025 (17)	0.050 (5)*
N12	0.50404 (15)	1.08991 (12)	0.16469 (11)	0.0351 (3)
H12D	0.4693	1.0909	0.0940	0.042*
H12E	0.5189	1.1555	0.2341	0.042*
C13	0.77339 (18)	1.06873 (15)	0.68743 (14)	0.0354 (3)
H13	0.7666	0.9821	0.6513	0.043*
C14	0.8361 (2)	1.14393 (17)	0.81604 (14)	0.0442 (4)
H14	0.8716	1.1077	0.8669	0.053*
C15	0.84680 (19)	1.27077 (16)	0.86998 (14)	0.0415 (4)
H15	0.8915	1.3216	0.9571	0.050*
C16	0.79161 (18)	1.32329 (15)	0.79563 (14)	0.0380 (3)
H16	0.7973	1.4096	0.8324	0.046*
C17	0.72806 (16)	1.24939 (13)	0.66731 (13)	0.0303 (3)
H17	0.6898	1.2854	0.6172	0.036*
C18	0.72058 (14)	1.12204 (12)	0.61204 (12)	0.0246 (3)
C19	0.66055 (14)	1.04497 (12)	0.47514 (12)	0.0229 (3)
C20	0.59803 (14)	0.88878 (12)	0.29832 (12)	0.0241 (3)
C21	0.53451 (15)	0.98768 (13)	0.16659 (12)	0.0259 (3)
C22	0.56405 (17)	0.78425 (13)	0.07957 (12)	0.0299 (3)
C23	0.7259 (2)	0.81007 (18)	0.08085 (16)	0.0448 (4)
H23A	0.7305	0.8189	0.0073	0.067*
H23B	0.7550	0.7382	0.0809	0.067*
H23C	0.7954	0.8896	0.1551	0.067*
C24	0.4530 (2)	0.65590 (15)	−0.03085 (14)	0.0453 (4)
H24A	0.3509	0.6423	−0.0298	0.068*
H24B	0.4821	0.5857	−0.0255	0.068*
H24C	0.4550	0.6576	−0.1078	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0236 (5)	0.0251 (6)	0.0355 (6)	0.0100 (5)	0.0086 (5)	0.0139 (5)
N2	0.0229 (5)	0.0228 (5)	0.0289 (6)	0.0065 (4)	0.0076 (4)	0.0118 (5)
N3	0.0225 (5)	0.0214 (5)	0.0321 (6)	0.0084 (4)	0.0077 (4)	0.0134 (5)
N4	0.0233 (5)	0.0258 (6)	0.0344 (6)	0.0108 (5)	0.0077 (5)	0.0171 (5)
N5	0.0244 (6)	0.0218 (6)	0.0500 (7)	0.0107 (5)	0.0111 (5)	0.0182 (5)
N6	0.0245 (6)	0.0271 (6)	0.0507 (7)	0.0111 (5)	0.0087 (5)	0.0231 (6)
C1	0.0294 (7)	0.0337 (7)	0.0312 (7)	0.0123 (6)	0.0099 (6)	0.0147 (6)
C2	0.0272 (7)	0.0524 (9)	0.0390 (8)	0.0170 (7)	0.0117 (6)	0.0242 (7)
C3	0.0247 (7)	0.0509 (10)	0.0348 (8)	0.0019 (6)	0.0068 (6)	0.0178 (7)
C4	0.0362 (8)	0.0330 (8)	0.0391 (8)	0.0014 (6)	0.0133 (7)	0.0110 (7)
C5	0.0314 (7)	0.0307 (7)	0.0369 (8)	0.0098 (6)	0.0142 (6)	0.0141 (6)
C6	0.0247 (6)	0.0289 (7)	0.0249 (6)	0.0088 (5)	0.0094 (5)	0.0131 (5)
C7	0.0250 (6)	0.0255 (6)	0.0243 (6)	0.0095 (5)	0.0089 (5)	0.0119 (5)
C8	0.0261 (6)	0.0247 (6)	0.0287 (7)	0.0123 (5)	0.0091 (5)	0.0138 (5)
C9	0.0234 (6)	0.0265 (6)	0.0258 (6)	0.0118 (5)	0.0083 (5)	0.0135 (5)
C10	0.0226 (6)	0.0254 (6)	0.0337 (7)	0.0102 (5)	0.0079 (5)	0.0170 (6)
C11	0.0401 (8)	0.0437 (9)	0.0374 (8)	0.0147 (7)	0.0127 (7)	0.0240 (7)
C12	0.0282 (7)	0.0275 (7)	0.0421 (8)	0.0079 (6)	0.0079 (6)	0.0150 (6)
N7	0.0292 (6)	0.0240 (5)	0.0253 (5)	0.0106 (4)	0.0097 (5)	0.0136 (5)
N8	0.0303 (6)	0.0235 (5)	0.0230 (5)	0.0106 (5)	0.0087 (4)	0.0108 (4)
N9	0.0338 (6)	0.0217 (5)	0.0234 (5)	0.0120 (5)	0.0089 (5)	0.0120 (4)
N10	0.0444 (7)	0.0268 (6)	0.0256 (6)	0.0168 (5)	0.0106 (5)	0.0145 (5)
N11	0.0423 (7)	0.0218 (6)	0.0277 (6)	0.0149 (5)	0.0131 (5)	0.0145 (5)
N12	0.0555 (8)	0.0305 (6)	0.0254 (6)	0.0247 (6)	0.0116 (5)	0.0154 (5)
C13	0.0460 (9)	0.0344 (8)	0.0307 (7)	0.0201 (7)	0.0126 (6)	0.0175 (6)
C14	0.0575 (10)	0.0513 (10)	0.0294 (8)	0.0273 (8)	0.0115 (7)	0.0226 (7)
C15	0.0479 (9)	0.0456 (9)	0.0238 (7)	0.0158 (7)	0.0103 (6)	0.0115 (7)
C16	0.0460 (9)	0.0313 (8)	0.0320 (8)	0.0129 (7)	0.0155 (7)	0.0104 (6)
C17	0.0342 (7)	0.0301 (7)	0.0305 (7)	0.0134 (6)	0.0132 (6)	0.0161 (6)
C18	0.0227 (6)	0.0271 (7)	0.0258 (6)	0.0090 (5)	0.0099 (5)	0.0136 (5)
C19	0.0204 (6)	0.0227 (6)	0.0277 (6)	0.0074 (5)	0.0092 (5)	0.0141 (5)
C20	0.0244 (6)	0.0233 (6)	0.0286 (6)	0.0097 (5)	0.0099 (5)	0.0153 (5)
C21	0.0286 (7)	0.0258 (6)	0.0250 (6)	0.0105 (5)	0.0080 (5)	0.0144 (5)
C22	0.0424 (8)	0.0254 (7)	0.0255 (7)	0.0158 (6)	0.0121 (6)	0.0135 (6)
C23	0.0535 (10)	0.0545 (10)	0.0475 (9)	0.0301 (9)	0.0285 (8)	0.0322 (8)
C24	0.0689 (12)	0.0285 (8)	0.0302 (8)	0.0170 (8)	0.0100 (8)	0.0111 (6)

Geometric parameters (Å, º) top

N1—C8	1.3200 (17)	N7—C20	1.3170 (17)
N1—C7	1.3761 (17)	N7—C19	1.3758 (16)
N2—C7	1.3224 (17)	N8—C19	1.3246 (16)
N2—N3	1.3869 (15)	N8—N9	1.3818 (15)
N3—C8	1.3561 (16)	N9—C20	1.3508 (16)
N3—C9	1.4078 (16)	N9—C21	1.4054 (16)
N4—C9	1.2803 (17)	N10—C21	1.2811 (17)
N4—C10	1.4636 (16)	N10—C22	1.4631 (17)
N5—C8	1.3403 (17)	N11—C20	1.3457 (17)
N5—C10	1.4819 (17)	N11—C22	1.4828 (17)
N5—H5N	0.874 (17)	N11—H11N	0.810 (19)
N6—C9	1.3350 (16)	N12—C21	1.3353 (17)
N6—H6A	0.87	N12—H12D	0.87
N6—H6B	0.87	N12—H12E	0.87
C1—C2	1.386 (2)	C13—C14	1.387 (2)
C1—C6	1.3948 (19)	C13—C18	1.3912 (19)
C1—H1	0.94	C13—H13	0.94
C2—C3	1.379 (2)	C14—C15	1.374 (2)
C2—H2	0.94	C14—H14	0.94
C3—C4	1.379 (2)	C15—C16	1.381 (2)
C3—H3	0.94	C15—H15	0.94
C4—C5	1.386 (2)	C16—C17	1.382 (2)
C4—H4	0.94	C16—H16	0.94
C5—C6	1.3919 (19)	C17—C18	1.3905 (19)
C5—H5	0.94	C17—H17	0.94
C6—C7	1.4728 (18)	C18—C19	1.4732 (18)
C10—C12	1.5193 (19)	C22—C24	1.518 (2)
C10—C11	1.524 (2)	C22—C23	1.523 (2)
C11—H11A	0.97	C23—H23A	0.97
C11—H11B	0.97	C23—H23B	0.97
C11—H11C	0.97	C23—H23C	0.97
C12—H12A	0.97	C24—H24A	0.97
C12—H12B	0.97	C24—H24B	0.97
C12—H12C	0.97	C24—H24C	0.97

C8—N1—C7	102.36 (11)	C20—N7—C19	102.43 (10)
C7—N2—N3	101.17 (10)	C19—N8—N9	101.35 (10)
C8—N3—N2	109.71 (10)	C20—N9—N8	109.76 (10)
C8—N3—C9	121.45 (11)	C20—N9—C21	122.04 (11)
N2—N3—C9	127.86 (10)	N8—N9—C21	128.07 (10)
C9—N4—C10	119.88 (11)	C21—N10—C22	120.53 (11)
C8—N5—C10	117.54 (11)	C20—N11—C22	117.96 (11)
C8—N5—H5N	120.0 (11)	C20—N11—H11N	118.6 (13)
C10—N5—H5N	118.8 (11)	C22—N11—H11N	119.8 (13)
C9—N6—H6A	120.0	C21—N12—H12D	120.0
C9—N6—H6B	120.0	C21—N12—H12E	120.0
H6A—N6—H6B	120.0	H12D—N12—H12E	120.0
C2—C1—C6	120.45 (14)	C14—C13—C18	119.75 (14)
C2—C1—H1	119.8	C14—C13—H13	120.1
C6—C1—H1	119.8	C18—C13—H13	120.1
C3—C2—C1	120.26 (14)	C15—C14—C13	120.70 (14)
C3—C2—H2	119.9	C15—C14—H14	119.7
C1—C2—H2	119.9	C13—C14—H14	119.7
C2—C3—C4	119.56 (14)	C14—C15—C16	119.75 (14)
C2—C3—H3	120.2	C14—C15—H15	120.1
C4—C3—H3	120.2	C16—C15—H15	120.1
C3—C4—C5	120.88 (15)	C15—C16—C17	120.25 (14)
C3—C4—H4	119.6	C15—C16—H16	119.9
C5—C4—H4	119.6	C17—C16—H16	119.9
C4—C5—C6	119.89 (14)	C16—C17—C18	120.23 (13)
C4—C5—H5	120.1	C16—C17—H17	119.9
C6—C5—H5	120.1	C18—C17—H17	119.9
C5—C6—C1	118.95 (13)	C17—C18—C13	119.28 (13)
C5—C6—C7	121.50 (12)	C17—C18—C19	120.54 (12)
C1—C6—C7	119.54 (12)	C13—C18—C19	120.16 (12)
N2—C7—N1	116.11 (11)	N8—C19—N7	115.68 (11)
N2—C7—C6	123.05 (12)	N8—C19—C18	121.99 (11)
N1—C7—C6	120.78 (11)	N7—C19—C18	122.21 (11)
N1—C8—N5	130.97 (12)	N7—C20—N11	130.98 (12)
N1—C8—N3	110.62 (11)	N7—C20—N9	110.77 (11)
N5—C8—N3	118.40 (12)	N11—C20—N9	118.24 (11)
N4—C9—N6	124.39 (12)	N10—C21—N12	123.95 (12)
N4—C9—N3	119.53 (11)	N10—C21—N9	119.94 (12)
N6—C9—N3	116.08 (11)	N12—C21—N9	116.11 (11)
N4—C10—N5	110.85 (10)	N10—C22—N11	111.25 (11)
N4—C10—C12	108.60 (11)	N10—C22—C24	107.89 (12)
N5—C10—C12	107.48 (11)	N11—C22—C24	107.66 (12)
N4—C10—C11	109.05 (11)	N10—C22—C23	109.33 (12)
N5—C10—C11	110.48 (11)	N11—C22—C23	109.52 (12)
C12—C10—C11	110.36 (12)	C24—C22—C23	111.19 (13)
C10—C11—H11A	109.5	C22—C23—H23A	109.5
C10—C11—H11B	109.5	C22—C23—H23B	109.5
H11A—C11—H11B	109.5	H23A—C23—H23B	109.5
C10—C11—H11C	109.5	C22—C23—H23C	109.5
H11A—C11—H11C	109.5	H23A—C23—H23C	109.5
H11B—C11—H11C	109.5	H23B—C23—H23C	109.5
C10—C12—H12A	109.5	C22—C24—H24A	109.5
C10—C12—H12B	109.5	C22—C24—H24B	109.5
H12A—C12—H12B	109.5	H24A—C24—H24B	109.5
C10—C12—H12C	109.5	C22—C24—H24C	109.5
H12A—C12—H12C	109.5	H24A—C24—H24C	109.5
H12B—C12—H12C	109.5	H24B—C24—H24C	109.5

C7—N2—N3—C8	1.37 (13)	C19—N8—N9—C20	1.11 (13)
C7—N2—N3—C9	170.10 (12)	C19—N8—N9—C21	177.04 (12)
C6—C1—C2—C3	−0.1 (2)	C18—C13—C14—C15	−0.1 (3)
C1—C2—C3—C4	0.7 (2)	C13—C14—C15—C16	1.4 (3)
C2—C3—C4—C5	−0.4 (2)	C14—C15—C16—C17	−1.1 (2)
C3—C4—C5—C6	−0.5 (2)	C15—C16—C17—C18	−0.6 (2)
C4—C5—C6—C1	1.1 (2)	C16—C17—C18—C13	2.0 (2)
C4—C5—C6—C7	−177.98 (13)	C16—C17—C18—C19	−176.71 (13)
C2—C1—C6—C5	−0.8 (2)	C14—C13—C18—C17	−1.6 (2)
C2—C1—C6—C7	178.33 (13)	C14—C13—C18—C19	177.07 (14)
N3—N2—C7—N1	−0.93 (14)	N9—N8—C19—N7	−0.54 (14)
N3—N2—C7—C6	176.30 (11)	N9—N8—C19—C18	175.52 (11)
C8—N1—C7—N2	0.12 (15)	C20—N7—C19—N8	−0.24 (14)
C8—N1—C7—C6	−177.18 (12)	C20—N7—C19—C18	−176.29 (11)
C5—C6—C7—N2	−9.5 (2)	C17—C18—C19—N8	7.11 (19)
C1—C6—C7—N2	171.34 (12)	C13—C18—C19—N8	−171.56 (13)
C5—C6—C7—N1	167.56 (13)	C17—C18—C19—N7	−177.08 (12)
C1—C6—C7—N1	−11.56 (19)	C13—C18—C19—N7	4.24 (19)
C7—N1—C8—N5	−178.18 (14)	C19—N7—C20—N11	−177.73 (14)
C7—N1—C8—N3	0.80 (14)	C19—N7—C20—N9	0.96 (14)
C10—N5—C8—N1	−161.07 (14)	C22—N11—C20—N7	−158.17 (13)
C10—N5—C8—N3	20.01 (18)	C22—N11—C20—N9	23.22 (18)
N2—N3—C8—N1	−1.44 (15)	N8—N9—C20—N7	−1.38 (15)
C9—N3—C8—N1	−171.02 (11)	C21—N9—C20—N7	−177.60 (11)
N2—N3—C8—N5	177.69 (11)	N8—N9—C20—N11	177.50 (11)
C9—N3—C8—N5	8.11 (19)	C21—N9—C20—N11	1.28 (19)
C10—N4—C9—N6	172.98 (13)	C22—N10—C21—N12	174.81 (13)
C10—N4—C9—N3	−7.26 (19)	C22—N10—C21—N9	−6.3 (2)
C8—N3—C9—N4	−15.29 (19)	C20—N9—C21—N10	−10.5 (2)
N2—N3—C9—N4	177.17 (12)	N8—N9—C21—N10	174.01 (13)
C8—N3—C9—N6	164.48 (12)	C20—N9—C21—N12	168.51 (12)
N2—N3—C9—N6	−3.06 (19)	N8—N9—C21—N12	−7.0 (2)
C9—N4—C10—N5	32.61 (17)	C21—N10—C22—N11	28.29 (18)
C9—N4—C10—C12	150.47 (13)	C21—N10—C22—C24	146.15 (14)
C9—N4—C10—C11	−89.23 (15)	C21—N10—C22—C23	−92.80 (16)
C8—N5—C10—N4	−39.04 (16)	C20—N11—C22—N10	−36.86 (17)
C8—N5—C10—C12	−157.58 (12)	C20—N11—C22—C24	−154.87 (13)
C8—N5—C10—C11	81.96 (15)	C20—N11—C22—C23	84.11 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···N7	0.874 (17)	2.150 (17)	2.9955 (16)	163 (2)
N6—H6A···N4ⁱ	0.87	2.08	2.9491 (16)	172
N12—H12D···N10ⁱⁱ	0.87	2.17	2.9844 (16)	156
N12—H12E···N2ⁱⁱⁱ	0.87	2.35	3.1119 (16)	146
N6—H6B···N8^iv	0.87	2.41	3.1751 (16)	147

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄N₆
M_r	242.29
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	9.7224 (5), 11.9752 (6), 12.4432 (6)
α, β, γ (°)	112.200 (1), 103.737 (1), 104.161 (1)
V (Å³)	1209.58 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.38 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.931, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	15995, 5549, 4621
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.121, 1.06
No. of reflections	5549
No. of parameters	337
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.29

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2003), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···N7	0.874 (17)	2.150 (17)	2.9955 (16)	163 (2)
N6—H6A···N4ⁱ	0.87	2.08	2.9491 (16)	172
N12—H12D···N10ⁱⁱ	0.87	2.17	2.9844 (16)	156
N12—H12E···N2ⁱⁱⁱ	0.87	2.35	3.1119 (16)	146
N6—H6B···N8^iv	0.87	2.41	3.1751 (16)	147

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

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