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Acta Cryst. (2007). E63, o2797    [ doi:10.1107/S1600536807021022 ]

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

Abstract top

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.

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).

Refinement top

Atom H5N and H11N were located in a difference map and refined isotropically. The remaining H atoms were placed in calculated positions (N—H = 0.87 Å and C—H = 0.94 or 0.97 Å), and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(methyl C). A rotating group model was used for the methyl groups.

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
[Figure 1] Fig. 1. The annular tautomerism in (I).
[Figure 2] 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.
[Figure 3] 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.
[Figure 4] 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
C12H14N6Z = 4
Mr = 242.29F(000) = 512
Triclinic, P1Dx = 1.331 Mg m−3
Hall symbol: -P 1Melting point: 482 K
a = 9.7224 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.9752 (6) ÅCell parameters from 4987 reflections
c = 12.4432 (6) Åθ = 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) Å30.40 × 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-detector4621 reflections with I > 2σ(I)
graphiteRint = 0.026
φ and ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		h = −12→12
Tmin = 0.931, Tmax = 0.980k = −15→15
15995 measured reflectionsl = −16→16
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0629P)2 + 0.25P]
where P = (Fo2 + 2Fc2)/3
5549 reflections(Δ/σ)max = 0.001
337 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C12H14N6γ = 104.161 (1)°
Mr = 242.29V = 1209.58 (10) Å3
Triclinic, P1Z = 4
a = 9.7224 (5) ÅMo Kα radiation
b = 11.9752 (6) ŵ = 0.09 mm−1
c = 12.4432 (6) ÅT = 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)
Tmin = 0.931, Tmax = 0.980Rint = 0.026
15995 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121Δρmax = 0.30 e Å−3
S = 1.06Δρmin = −0.28 e Å−3
5549 reflectionsAbsolute structure: ?
337 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
N10.43352 (12)0.53590 (11)0.34655 (11)0.0283 (3)
N20.49145 (12)0.35638 (10)0.32551 (10)0.0257 (2)
N30.62201 (12)0.46598 (10)0.37342 (10)0.0254 (2)
N40.88222 (12)0.58752 (11)0.46028 (11)0.0270 (2)
N50.69510 (13)0.68668 (11)0.43546 (12)0.0316 (3)
H5N0.6728 (19)0.7549 (16)0.4426 (15)0.037 (4)*
N60.79574 (13)0.37717 (11)0.43315 (12)0.0331 (3)
H6A0.88770.38060.46440.040*
H6B0.71770.30680.40730.040*
C10.11373 (16)0.38462 (14)0.25729 (13)0.0317 (3)
H10.14750.47580.29720.038*
C2−0.04123 (17)0.31081 (16)0.20182 (14)0.0381 (3)
H2−0.11200.35210.20450.046*
C3−0.09205 (17)0.17701 (16)0.14279 (14)0.0409 (4)
H3−0.19720.12700.10440.049*
C40.01239 (18)0.11703 (15)0.14052 (15)0.0406 (4)
H4−0.02220.02580.10070.049*
C50.16773 (16)0.18946 (14)0.19612 (14)0.0336 (3)
H50.23770.14740.19450.040*
C60.21989 (14)0.32455 (13)0.25427 (12)0.0261 (3)
C70.38395 (14)0.40484 (12)0.31078 (12)0.0248 (3)
C80.58319 (15)0.57033 (12)0.38609 (12)0.0257 (3)
C90.77452 (14)0.48004 (12)0.42477 (12)0.0244 (3)
C100.84763 (14)0.68883 (13)0.43383 (13)0.0264 (3)
C110.85505 (18)0.66838 (16)0.30710 (14)0.0391 (4)
H11A0.95240.66280.30520.059*
H11B0.84430.74090.29340.059*
H11C0.77310.58840.24210.059*
C120.96425 (16)0.82034 (14)0.53578 (14)0.0345 (3)
H12A0.95850.83190.61590.052*
H12B0.94300.88850.51910.052*
H12C1.06570.82460.53740.052*
N70.64515 (12)0.91698 (10)0.41712 (10)0.0253 (2)
N80.62672 (13)1.09681 (10)0.40021 (10)0.0257 (2)
N90.58770 (13)0.99346 (10)0.28465 (10)0.0257 (2)
N100.51588 (14)0.88737 (11)0.06878 (10)0.0311 (3)
N110.55846 (14)0.77685 (11)0.19483 (11)0.0289 (3)
H11N0.562 (2)0.7133 (19)0.2025 (17)0.050 (5)*
N120.50404 (15)1.08991 (12)0.16469 (11)0.0351 (3)
H12D0.46931.09090.09400.042*
H12E0.51891.15550.23410.042*
C130.77339 (18)1.06873 (15)0.68743 (14)0.0354 (3)
H130.76660.98210.65130.043*
C140.8361 (2)1.14393 (17)0.81604 (14)0.0442 (4)
H140.87161.10770.86690.053*
C150.84680 (19)1.27077 (16)0.86998 (14)0.0415 (4)
H150.89151.32160.95710.050*
C160.79161 (18)1.32329 (15)0.79563 (14)0.0380 (3)
H160.79731.40960.83240.046*
C170.72806 (16)1.24939 (13)0.66731 (13)0.0303 (3)
H170.68981.28540.61720.036*
C180.72058 (14)1.12204 (12)0.61204 (12)0.0246 (3)
C190.66055 (14)1.04497 (12)0.47514 (12)0.0229 (3)
C200.59803 (14)0.88878 (12)0.29832 (12)0.0241 (3)
C210.53451 (15)0.98768 (13)0.16659 (12)0.0259 (3)
C220.56405 (17)0.78425 (13)0.07957 (12)0.0299 (3)
C230.7259 (2)0.81007 (18)0.08085 (16)0.0448 (4)
H23A0.73050.81890.00730.067*
H23B0.75500.73820.08090.067*
H23C0.79540.88960.15510.067*
C240.4530 (2)0.65590 (15)−0.03085 (14)0.0453 (4)
H24A0.35090.6423−0.02980.068*
H24B0.48210.5857−0.02550.068*
H24C0.45500.6576−0.10780.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0236 (5)0.0251 (6)0.0355 (6)0.0100 (5)0.0086 (5)0.0139 (5)
N20.0229 (5)0.0228 (5)0.0289 (6)0.0065 (4)0.0076 (4)0.0118 (5)
N30.0225 (5)0.0214 (5)0.0321 (6)0.0084 (4)0.0077 (4)0.0134 (5)
N40.0233 (5)0.0258 (6)0.0344 (6)0.0108 (5)0.0077 (5)0.0171 (5)
N50.0244 (6)0.0218 (6)0.0500 (7)0.0107 (5)0.0111 (5)0.0182 (5)
N60.0245 (6)0.0271 (6)0.0507 (7)0.0111 (5)0.0087 (5)0.0231 (6)
C10.0294 (7)0.0337 (7)0.0312 (7)0.0123 (6)0.0099 (6)0.0147 (6)
C20.0272 (7)0.0524 (9)0.0390 (8)0.0170 (7)0.0117 (6)0.0242 (7)
C30.0247 (7)0.0509 (10)0.0348 (8)0.0019 (6)0.0068 (6)0.0178 (7)
C40.0362 (8)0.0330 (8)0.0391 (8)0.0014 (6)0.0133 (7)0.0110 (7)
C50.0314 (7)0.0307 (7)0.0369 (8)0.0098 (6)0.0142 (6)0.0141 (6)
C60.0247 (6)0.0289 (7)0.0249 (6)0.0088 (5)0.0094 (5)0.0131 (5)
C70.0250 (6)0.0255 (6)0.0243 (6)0.0095 (5)0.0089 (5)0.0119 (5)
C80.0261 (6)0.0247 (6)0.0287 (7)0.0123 (5)0.0091 (5)0.0138 (5)
C90.0234 (6)0.0265 (6)0.0258 (6)0.0118 (5)0.0083 (5)0.0135 (5)
C100.0226 (6)0.0254 (6)0.0337 (7)0.0102 (5)0.0079 (5)0.0170 (6)
C110.0401 (8)0.0437 (9)0.0374 (8)0.0147 (7)0.0127 (7)0.0240 (7)
C120.0282 (7)0.0275 (7)0.0421 (8)0.0079 (6)0.0079 (6)0.0150 (6)
N70.0292 (6)0.0240 (5)0.0253 (5)0.0106 (4)0.0097 (5)0.0136 (5)
N80.0303 (6)0.0235 (5)0.0230 (5)0.0106 (5)0.0087 (4)0.0108 (4)
N90.0338 (6)0.0217 (5)0.0234 (5)0.0120 (5)0.0089 (5)0.0120 (4)
N100.0444 (7)0.0268 (6)0.0256 (6)0.0168 (5)0.0106 (5)0.0145 (5)
N110.0423 (7)0.0218 (6)0.0277 (6)0.0149 (5)0.0131 (5)0.0145 (5)
N120.0555 (8)0.0305 (6)0.0254 (6)0.0247 (6)0.0116 (5)0.0154 (5)
C130.0460 (9)0.0344 (8)0.0307 (7)0.0201 (7)0.0126 (6)0.0175 (6)
C140.0575 (10)0.0513 (10)0.0294 (8)0.0273 (8)0.0115 (7)0.0226 (7)
C150.0479 (9)0.0456 (9)0.0238 (7)0.0158 (7)0.0103 (6)0.0115 (7)
C160.0460 (9)0.0313 (8)0.0320 (8)0.0129 (7)0.0155 (7)0.0104 (6)
C170.0342 (7)0.0301 (7)0.0305 (7)0.0134 (6)0.0132 (6)0.0161 (6)
C180.0227 (6)0.0271 (7)0.0258 (6)0.0090 (5)0.0099 (5)0.0136 (5)
C190.0204 (6)0.0227 (6)0.0277 (6)0.0074 (5)0.0092 (5)0.0141 (5)
C200.0244 (6)0.0233 (6)0.0286 (6)0.0097 (5)0.0099 (5)0.0153 (5)
C210.0286 (7)0.0258 (6)0.0250 (6)0.0105 (5)0.0080 (5)0.0144 (5)
C220.0424 (8)0.0254 (7)0.0255 (7)0.0158 (6)0.0121 (6)0.0135 (6)
C230.0535 (10)0.0545 (10)0.0475 (9)0.0301 (9)0.0285 (8)0.0322 (8)
C240.0689 (12)0.0285 (8)0.0302 (8)0.0170 (8)0.0100 (8)0.0111 (6)
Geometric parameters (Å, °) top
N1—C81.3200 (17)N7—C201.3170 (17)
N1—C71.3761 (17)N7—C191.3758 (16)
N2—C71.3224 (17)N8—C191.3246 (16)
N2—N31.3869 (15)N8—N91.3818 (15)
N3—C81.3561 (16)N9—C201.3508 (16)
N3—C91.4078 (16)N9—C211.4054 (16)
N4—C91.2803 (17)N10—C211.2811 (17)
N4—C101.4636 (16)N10—C221.4631 (17)
N5—C81.3403 (17)N11—C201.3457 (17)
N5—C101.4819 (17)N11—C221.4828 (17)
N5—H5N0.874 (17)N11—H11N0.810 (19)
N6—C91.3350 (16)N12—C211.3353 (17)
N6—H6A0.87N12—H12D0.87
N6—H6B0.87N12—H12E0.87
C1—C21.386 (2)C13—C141.387 (2)
C1—C61.3948 (19)C13—C181.3912 (19)
C1—H10.94C13—H130.94
C2—C31.379 (2)C14—C151.374 (2)
C2—H20.94C14—H140.94
C3—C41.379 (2)C15—C161.381 (2)
C3—H30.94C15—H150.94
C4—C51.386 (2)C16—C171.382 (2)
C4—H40.94C16—H160.94
C5—C61.3919 (19)C17—C181.3905 (19)
C5—H50.94C17—H170.94
C6—C71.4728 (18)C18—C191.4732 (18)
C10—C121.5193 (19)C22—C241.518 (2)
C10—C111.524 (2)C22—C231.523 (2)
C11—H11A0.97C23—H23A0.97
C11—H11B0.97C23—H23B0.97
C11—H11C0.97C23—H23C0.97
C12—H12A0.97C24—H24A0.97
C12—H12B0.97C24—H24B0.97
C12—H12C0.97C24—H24C0.97
C8—N1—C7102.36 (11)C20—N7—C19102.43 (10)
C7—N2—N3101.17 (10)C19—N8—N9101.35 (10)
C8—N3—N2109.71 (10)C20—N9—N8109.76 (10)
C8—N3—C9121.45 (11)C20—N9—C21122.04 (11)
N2—N3—C9127.86 (10)N8—N9—C21128.07 (10)
C9—N4—C10119.88 (11)C21—N10—C22120.53 (11)
C8—N5—C10117.54 (11)C20—N11—C22117.96 (11)
C8—N5—H5N120.0 (11)C20—N11—H11N118.6 (13)
C10—N5—H5N118.8 (11)C22—N11—H11N119.8 (13)
C9—N6—H6A120.0C21—N12—H12D120.0
C9—N6—H6B120.0C21—N12—H12E120.0
H6A—N6—H6B120.0H12D—N12—H12E120.0
C2—C1—C6120.45 (14)C14—C13—C18119.75 (14)
C2—C1—H1119.8C14—C13—H13120.1
C6—C1—H1119.8C18—C13—H13120.1
C3—C2—C1120.26 (14)C15—C14—C13120.70 (14)
C3—C2—H2119.9C15—C14—H14119.7
C1—C2—H2119.9C13—C14—H14119.7
C2—C3—C4119.56 (14)C14—C15—C16119.75 (14)
C2—C3—H3120.2C14—C15—H15120.1
C4—C3—H3120.2C16—C15—H15120.1
C3—C4—C5120.88 (15)C15—C16—C17120.25 (14)
C3—C4—H4119.6C15—C16—H16119.9
C5—C4—H4119.6C17—C16—H16119.9
C4—C5—C6119.89 (14)C16—C17—C18120.23 (13)
C4—C5—H5120.1C16—C17—H17119.9
C6—C5—H5120.1C18—C17—H17119.9
C5—C6—C1118.95 (13)C17—C18—C13119.28 (13)
C5—C6—C7121.50 (12)C17—C18—C19120.54 (12)
C1—C6—C7119.54 (12)C13—C18—C19120.16 (12)
N2—C7—N1116.11 (11)N8—C19—N7115.68 (11)
N2—C7—C6123.05 (12)N8—C19—C18121.99 (11)
N1—C7—C6120.78 (11)N7—C19—C18122.21 (11)
N1—C8—N5130.97 (12)N7—C20—N11130.98 (12)
N1—C8—N3110.62 (11)N7—C20—N9110.77 (11)
N5—C8—N3118.40 (12)N11—C20—N9118.24 (11)
N4—C9—N6124.39 (12)N10—C21—N12123.95 (12)
N4—C9—N3119.53 (11)N10—C21—N9119.94 (12)
N6—C9—N3116.08 (11)N12—C21—N9116.11 (11)
N4—C10—N5110.85 (10)N10—C22—N11111.25 (11)
N4—C10—C12108.60 (11)N10—C22—C24107.89 (12)
N5—C10—C12107.48 (11)N11—C22—C24107.66 (12)
N4—C10—C11109.05 (11)N10—C22—C23109.33 (12)
N5—C10—C11110.48 (11)N11—C22—C23109.52 (12)
C12—C10—C11110.36 (12)C24—C22—C23111.19 (13)
C10—C11—H11A109.5C22—C23—H23A109.5
C10—C11—H11B109.5C22—C23—H23B109.5
H11A—C11—H11B109.5H23A—C23—H23B109.5
C10—C11—H11C109.5C22—C23—H23C109.5
H11A—C11—H11C109.5H23A—C23—H23C109.5
H11B—C11—H11C109.5H23B—C23—H23C109.5
C10—C12—H12A109.5C22—C24—H24A109.5
C10—C12—H12B109.5C22—C24—H24B109.5
H12A—C12—H12B109.5H24A—C24—H24B109.5
C10—C12—H12C109.5C22—C24—H24C109.5
H12A—C12—H12C109.5H24A—C24—H24C109.5
H12B—C12—H12C109.5H24B—C24—H24C109.5
C7—N2—N3—C81.37 (13)C19—N8—N9—C201.11 (13)
C7—N2—N3—C9170.10 (12)C19—N8—N9—C21177.04 (12)
C6—C1—C2—C3−0.1 (2)C18—C13—C14—C15−0.1 (3)
C1—C2—C3—C40.7 (2)C13—C14—C15—C161.4 (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—C11.1 (2)C16—C17—C18—C132.0 (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—C7178.33 (13)C14—C13—C18—C19177.07 (14)
N3—N2—C7—N1−0.93 (14)N9—N8—C19—N7−0.54 (14)
N3—N2—C7—C6176.30 (11)N9—N8—C19—C18175.52 (11)
C8—N1—C7—N20.12 (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—N87.11 (19)
C1—C6—C7—N2171.34 (12)C13—C18—C19—N8−171.56 (13)
C5—C6—C7—N1167.56 (13)C17—C18—C19—N7−177.08 (12)
C1—C6—C7—N1−11.56 (19)C13—C18—C19—N74.24 (19)
C7—N1—C8—N5−178.18 (14)C19—N7—C20—N11−177.73 (14)
C7—N1—C8—N30.80 (14)C19—N7—C20—N90.96 (14)
C10—N5—C8—N1−161.07 (14)C22—N11—C20—N7−158.17 (13)
C10—N5—C8—N320.01 (18)C22—N11—C20—N923.22 (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—N5177.69 (11)N8—N9—C20—N11177.50 (11)
C9—N3—C8—N58.11 (19)C21—N9—C20—N111.28 (19)
C10—N4—C9—N6172.98 (13)C22—N10—C21—N12174.81 (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—N4177.17 (12)N8—N9—C21—N10174.01 (13)
C8—N3—C9—N6164.48 (12)C20—N9—C21—N12168.51 (12)
N2—N3—C9—N6−3.06 (19)N8—N9—C21—N12−7.0 (2)
C9—N4—C10—N532.61 (17)C21—N10—C22—N1128.29 (18)
C9—N4—C10—C12150.47 (13)C21—N10—C22—C24146.15 (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—C1181.96 (15)C20—N11—C22—C2384.11 (15)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···N70.874 (17)2.150 (17)2.9955 (16)163 (2)
N6—H6A···N4i0.872.082.9491 (16)172
N12—H12D···N10ii0.872.172.9844 (16)156
N12—H12E···N2iii0.872.353.1119 (16)146
N6—H6B···N8iv0.872.413.1751 (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.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···N70.874 (17)2.150 (17)2.9955 (16)163 (2)
N6—H6A···N4i0.872.082.9491 (16)172
N12—H12D···N10ii0.872.172.9844 (16)156
N12—H12E···N2iii0.872.353.1119 (16)146
N6—H6B···N8iv0.872.413.1751 (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.
Acknowledgements top

This work was supported by the Academic Research Fund from the National University of Singapore.

references
References top

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