2-Phenyl-1H-1,3,7,8-tetra­azacyclo­penta­[l]phenanthrene

Liu, D.-M.; Li, X.-Y.; Wang, X.-C.; Li, C.-X.; Liu, C.-B.

doi:10.1107/S1600536809017498

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1308

doi:10.1107/S1600536809017498

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2-Phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene

Dong-Ming Liu,^a Xiu-Ying Li,^b Xiang-Cheng Wang,^b Chun-Xiang Li ^b and Chun-Bo Liu ^b ^*

^aAffiliated Hospital, Jiangsu University, Zhenjiang 212001, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, People's Republic of China
^*Correspondence e-mail: liuchunbo431@yahoo.com.cn

(Received 10 May 2009; accepted 10 May 2009; online 20 May 2009)

There are two molecules in the asymmetric unit of the title compound, C₁₉H₁₂N₄, with dihedral angles of 2.41 (10) and 10.53 (12)° between the fused ring system and the pendant phenyl ring. In the crystal, molecules are linked into chains by N—H⋯N hydrogen bonds and aromatic π–π stacking interactions [shortest centroid–centroid distance = 3.6176 (16) Å] complete the structure.

Related literature

For the synthesis, see: Steck & Day (1943 ); For related structures, see: Che et al. (2008 ); Stephenson & Hardie (2006 ); Xi (2008 ).

Experimental

Crystal data

C₁₉H₁₂N₄
M_r = 296.33
Triclinic, $[P \overline 1]$
a = 10.016 (2) Å
b = 12.210 (2) Å
c = 12.415 (3) Å
α = 89.90 (3)°
β = 78.44 (3)°
γ = 77.96 (3)°
V = 1453.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 292 K
0.30 × 0.25 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.975, T_max = 0.984
14453 measured reflections
6587 independent reflections
3657 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.156
S = 1.01
6587 reflections
415 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N5ⁱ	0.86	2.10	2.932 (3)	164
N7—H7⋯N1	0.86	2.12	2.951 (2)	163
Symmetry code: (i) x, y-1, z.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017498/hb2971sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017498/hb2971Isup2.hkl

checkCIF report

Comment top

1,10-Phenanthroline (phen) or its derivatives, as an important chelating ligands with excellent coordinating abilities and fruitful aromatic systems, have been extensively used to build supramolecular architectures (Che, Liu et al., 2008; Stephenson, Hardie et al., 2006). We report here the synthesis and structure of the title compound, namely, C₁₉H₁₂N₄ (I), using the phen derivative 2-Phenyl-1H-1,3,7,8-tetraazacyclopenta- [l]phenanthrene (L).

The asymmetric unit of (I) consists of two independent L molecules (Fig.1). The two phenyl rings are slightly twisted with respect to the fused-ring system [dihedral angles = 1.34 and 1.54 °], which is different from a related compound that has been reported (Xi, 2008). In the crystal structure, N—H···N hydrogen bonds (Table 1) link the molecules into chains along the b axis. The neighbouring chains interact through π-π contact between two L ligands [centroid separation = 3.541 Å], leading to the ultimate supramolecular structure (Fig. 2).

Related literature top

For the synthesis, see: Steck & Day (1943); For related structures, see: Che et al. (2008); Stephenson & Hardie (2006); Xi (2008).

Experimental top

The L ligand was synthesized according to the literature method of Steck & Day (1943): a mixture of L, MnCl₂ and water in a molar ratio of 2:1:5000 was sealed in a Teflon-lined autoclave and heated to 413 K for 3 d. Upon cooling and opening the bomb, accidentally, pale yellow blocks of (I) were obtained.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I). Displacement ellipsoids are drawn at the 30% probability level (arbitrary spheres for the H atoms).
	Fig. 2. A view of the crystal packing, showing the N—H···N hydrogen bonds and π-π stacking interactions. H atoms have been omitted.

2-Phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene top

Crystal data top

C₁₉H₁₂N₄	Z = 4
M_r = 296.33	F(000) = 616
Triclinic, P1	D_x = 1.354 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.016 (2) Å	Cell parameters from 3449 reflections
b = 12.210 (2) Å	θ = 3.0–27.5°
c = 12.415 (3) Å	µ = 0.08 mm⁻¹
α = 89.90 (3)°	T = 292 K
β = 78.44 (3)°	Block, pale yellow
γ = 77.96 (3)°	0.30 × 0.25 × 0.20 mm
V = 1453.7 (5) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	6587 independent reflections
Radiation source: fine-focus sealed tube	3657 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→15
T_min = 0.975, T_max = 0.984	l = −16→16
14453 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0719P)² + 0.0624P] where P = (F_o² + 2F_c²)/3
6587 reflections	(Δ/σ)_max < 0.001
415 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₉H₁₂N₄	γ = 77.96 (3)°
M_r = 296.33	V = 1453.7 (5) Å³
Triclinic, P1	Z = 4
a = 10.016 (2) Å	Mo Kα radiation
b = 12.210 (2) Å	µ = 0.08 mm⁻¹
c = 12.415 (3) Å	T = 292 K
α = 89.90 (3)°	0.30 × 0.25 × 0.20 mm
β = 78.44 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	6587 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3657 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.984	R_int = 0.048
14453 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.01	Δρ_max = 0.41 e Å⁻³
6587 reflections	Δρ_min = −0.20 e Å⁻³
415 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
C1	−0.0622 (2)	0.23344 (19)	0.81330 (18)	0.0490 (6)
H1	−0.1221	0.2801	0.8697	0.059*
C2	−0.0895 (2)	0.12895 (19)	0.79496 (18)	0.0484 (6)
H2	−0.1658	0.1068	0.8380	0.058*
C3	−0.0027 (2)	0.05936 (18)	0.71295 (17)	0.0450 (5)
H3A	−0.0182	−0.0115	0.7001	0.054*
C4	0.1104 (2)	0.09578 (17)	0.64798 (15)	0.0372 (5)
C5	0.2049 (2)	0.03323 (16)	0.55681 (16)	0.0389 (5)
C6	0.3066 (2)	0.07524 (17)	0.48872 (16)	0.0399 (5)
C7	0.3291 (2)	0.18394 (18)	0.51052 (16)	0.0411 (5)
C8	0.4316 (2)	0.2316 (2)	0.44514 (19)	0.0511 (6)
H8	0.4916	0.1918	0.3843	0.061*
C9	0.4418 (3)	0.3372 (2)	0.4723 (2)	0.0620 (7)
H9	0.5088	0.3707	0.4300	0.074*
C10	0.3510 (3)	0.3944 (2)	0.5639 (2)	0.0602 (7)
H10	0.3590	0.4665	0.5808	0.072*
C11	0.2416 (2)	0.24813 (17)	0.60234 (16)	0.0396 (5)
C12	0.1303 (2)	0.20394 (17)	0.67106 (15)	0.0376 (5)
C13	0.3167 (2)	−0.08769 (19)	0.42188 (16)	0.0441 (5)
C14	0.3576 (2)	−0.1902 (2)	0.35036 (18)	0.0471 (6)
C15	0.3037 (3)	−0.2845 (2)	0.3759 (2)	0.0621 (7)
H15	0.2408	−0.2852	0.4419	0.075*
C16	0.3416 (3)	−0.3775 (2)	0.3051 (2)	0.0745 (8)
H16	0.3036	−0.4401	0.3231	0.089*
C17	0.4350 (3)	−0.3777 (3)	0.2086 (3)	0.0802 (10)
H17	0.4613	−0.4406	0.1609	0.096*
C18	0.4895 (3)	−0.2857 (3)	0.1823 (2)	0.0781 (9)
H18	0.5529	−0.2861	0.1163	0.094*
C19	0.4521 (3)	−0.1917 (2)	0.2523 (2)	0.0631 (7)
H19	0.4904	−0.1295	0.2335	0.076*
C20	−0.0061 (2)	0.71983 (19)	0.57979 (18)	0.0495 (6)
H20	−0.0384	0.7605	0.5233	0.059*
C21	−0.0429 (2)	0.61739 (19)	0.60084 (18)	0.0485 (6)
H21	−0.0989	0.5910	0.5600	0.058*
C22	0.0046 (2)	0.55589 (18)	0.68273 (17)	0.0455 (5)
H22	−0.0169	0.4862	0.6976	0.055*
C23	0.0864 (2)	0.59938 (17)	0.74404 (16)	0.0382 (5)
C24	0.1393 (2)	0.54495 (17)	0.83266 (16)	0.0379 (5)
C25	0.2102 (2)	0.59356 (18)	0.89767 (16)	0.0406 (5)
C26	0.2425 (2)	0.70078 (18)	0.87370 (16)	0.0405 (5)
C27	0.3175 (2)	0.7535 (2)	0.93361 (18)	0.0510 (6)
H27	0.3498	0.7192	0.9931	0.061*
C28	0.3424 (3)	0.8564 (2)	0.9033 (2)	0.0599 (7)
H28	0.3910	0.8936	0.9423	0.072*
C29	0.2938 (3)	0.9040 (2)	0.8131 (2)	0.0611 (7)
H29	0.3119	0.9737	0.7931	0.073*
C30	0.1977 (2)	0.75555 (17)	0.78341 (16)	0.0404 (5)
C31	0.1167 (2)	0.70490 (17)	0.71880 (16)	0.0384 (5)
C32	0.1928 (2)	0.43446 (18)	0.96433 (16)	0.0415 (5)
C33	0.2076 (2)	0.33528 (19)	1.03149 (17)	0.0447 (5)
C34	0.1535 (3)	0.2436 (2)	1.0129 (2)	0.0654 (7)
H34	0.1045	0.2443	0.9566	0.078*
C35	0.1709 (3)	0.1517 (3)	1.0762 (2)	0.0797 (9)
H35	0.1332	0.0908	1.0627	0.096*
C36	0.2433 (3)	0.1487 (3)	1.1591 (2)	0.0751 (8)
H36	0.2558	0.0859	1.2015	0.090*
C37	0.2964 (3)	0.2383 (3)	1.1787 (2)	0.0709 (8)
H37	0.3447	0.2371	1.2355	0.085*
C38	0.2797 (3)	0.3312 (2)	1.11548 (19)	0.0603 (7)
H38	0.3174	0.3918	1.1297	0.072*
N1	0.04442 (19)	0.27076 (14)	0.75517 (14)	0.0444 (5)
N2	0.2540 (2)	0.35239 (16)	0.62830 (15)	0.0488 (5)
N3	0.21246 (18)	−0.07178 (14)	0.51377 (13)	0.0429 (4)
H3	0.1617	−0.1184	0.5395	0.052*
N4	0.37586 (19)	0.00010 (16)	0.40376 (14)	0.0461 (5)
N5	0.0722 (2)	0.76364 (15)	0.63503 (14)	0.0460 (5)
N6	0.2236 (2)	0.85701 (16)	0.75407 (15)	0.0505 (5)
N7	0.12911 (18)	0.44362 (14)	0.87635 (13)	0.0403 (4)
H7	0.0899	0.3947	0.8529	0.048*
N8	0.24317 (19)	0.52409 (15)	0.98030 (14)	0.0441 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0537 (14)	0.0477 (14)	0.0407 (12)	−0.0078 (11)	−0.0015 (11)	−0.0058 (11)
C2	0.0496 (13)	0.0490 (14)	0.0437 (12)	−0.0115 (11)	−0.0017 (11)	0.0028 (11)
C3	0.0518 (13)	0.0392 (12)	0.0451 (12)	−0.0118 (10)	−0.0098 (11)	0.0036 (10)
C4	0.0449 (12)	0.0340 (11)	0.0327 (10)	−0.0070 (9)	−0.0098 (9)	0.0033 (9)
C5	0.0489 (12)	0.0327 (11)	0.0346 (11)	−0.0057 (10)	−0.0103 (10)	0.0025 (9)
C6	0.0452 (12)	0.0406 (12)	0.0347 (11)	−0.0076 (10)	−0.0118 (10)	0.0055 (9)
C7	0.0446 (12)	0.0435 (13)	0.0382 (11)	−0.0108 (10)	−0.0140 (10)	0.0070 (10)
C8	0.0479 (14)	0.0620 (16)	0.0468 (13)	−0.0183 (12)	−0.0106 (11)	0.0090 (11)
C9	0.0588 (16)	0.0709 (18)	0.0647 (16)	−0.0337 (14)	−0.0118 (13)	0.0143 (14)
C10	0.0650 (17)	0.0540 (16)	0.0692 (17)	−0.0279 (13)	−0.0156 (14)	0.0053 (13)
C11	0.0452 (12)	0.0385 (12)	0.0385 (11)	−0.0092 (10)	−0.0162 (10)	0.0054 (9)
C12	0.0446 (12)	0.0364 (11)	0.0328 (10)	−0.0066 (9)	−0.0121 (9)	0.0031 (9)
C13	0.0481 (13)	0.0463 (13)	0.0351 (11)	−0.0030 (11)	−0.0094 (10)	0.0002 (10)
C14	0.0477 (13)	0.0498 (14)	0.0415 (12)	−0.0009 (11)	−0.0139 (10)	−0.0055 (11)
C15	0.0723 (17)	0.0529 (16)	0.0540 (15)	−0.0022 (13)	−0.0077 (13)	−0.0143 (13)
C16	0.086 (2)	0.0588 (18)	0.0757 (19)	−0.0058 (15)	−0.0186 (17)	−0.0197 (15)
C17	0.0701 (19)	0.081 (2)	0.082 (2)	0.0056 (17)	−0.0209 (17)	−0.0417 (18)
C18	0.0578 (17)	0.103 (3)	0.0629 (17)	−0.0055 (17)	0.0007 (14)	−0.0354 (18)
C19	0.0541 (15)	0.0762 (18)	0.0535 (15)	−0.0076 (13)	−0.0047 (12)	−0.0152 (14)
C20	0.0639 (15)	0.0469 (14)	0.0419 (12)	−0.0100 (12)	−0.0224 (11)	0.0082 (10)
C21	0.0564 (14)	0.0453 (14)	0.0483 (13)	−0.0087 (11)	−0.0235 (11)	0.0018 (11)
C22	0.0580 (14)	0.0366 (12)	0.0465 (12)	−0.0103 (11)	−0.0209 (11)	0.0018 (10)
C23	0.0429 (12)	0.0340 (12)	0.0366 (11)	−0.0050 (9)	−0.0092 (9)	−0.0008 (9)
C24	0.0468 (12)	0.0322 (11)	0.0343 (10)	−0.0053 (9)	−0.0103 (9)	0.0005 (9)
C25	0.0449 (12)	0.0423 (12)	0.0330 (11)	−0.0043 (10)	−0.0094 (9)	0.0003 (9)
C26	0.0414 (12)	0.0431 (13)	0.0361 (11)	−0.0079 (10)	−0.0069 (9)	−0.0017 (9)
C27	0.0543 (14)	0.0593 (16)	0.0434 (13)	−0.0175 (12)	−0.0142 (11)	−0.0027 (11)
C28	0.0663 (16)	0.0649 (17)	0.0567 (15)	−0.0290 (14)	−0.0160 (13)	−0.0051 (13)
C29	0.0739 (18)	0.0540 (16)	0.0648 (16)	−0.0317 (14)	−0.0175 (14)	0.0048 (13)
C30	0.0456 (12)	0.0366 (12)	0.0393 (11)	−0.0104 (10)	−0.0073 (10)	−0.0009 (9)
C31	0.0434 (12)	0.0368 (12)	0.0337 (11)	−0.0052 (9)	−0.0087 (9)	−0.0003 (9)
C32	0.0459 (13)	0.0442 (13)	0.0321 (10)	−0.0027 (10)	−0.0095 (9)	0.0022 (9)
C33	0.0474 (13)	0.0467 (13)	0.0350 (11)	−0.0013 (10)	−0.0059 (10)	0.0067 (10)
C34	0.085 (2)	0.0583 (17)	0.0612 (16)	−0.0206 (15)	−0.0298 (14)	0.0237 (13)
C35	0.103 (2)	0.0656 (19)	0.079 (2)	−0.0267 (17)	−0.0296 (18)	0.0329 (16)
C36	0.080 (2)	0.070 (2)	0.0656 (18)	−0.0016 (16)	−0.0087 (16)	0.0328 (15)
C37	0.0715 (19)	0.088 (2)	0.0504 (15)	−0.0020 (17)	−0.0226 (14)	0.0220 (15)
C38	0.0646 (17)	0.0678 (18)	0.0473 (14)	−0.0062 (14)	−0.0167 (12)	0.0108 (13)
N1	0.0540 (11)	0.0385 (10)	0.0400 (10)	−0.0086 (9)	−0.0094 (9)	−0.0009 (8)
N2	0.0573 (12)	0.0411 (11)	0.0536 (11)	−0.0171 (9)	−0.0179 (9)	0.0032 (9)
N3	0.0521 (11)	0.0370 (10)	0.0377 (10)	−0.0091 (8)	−0.0049 (9)	−0.0007 (8)
N4	0.0486 (11)	0.0494 (12)	0.0369 (9)	−0.0057 (9)	−0.0052 (8)	−0.0018 (9)
N5	0.0581 (12)	0.0423 (11)	0.0408 (10)	−0.0114 (9)	−0.0165 (9)	0.0046 (8)
N6	0.0622 (13)	0.0431 (11)	0.0516 (11)	−0.0204 (10)	−0.0146 (10)	0.0027 (9)
N7	0.0514 (11)	0.0349 (10)	0.0373 (9)	−0.0093 (8)	−0.0149 (8)	0.0042 (8)
N8	0.0496 (11)	0.0466 (11)	0.0369 (9)	−0.0079 (9)	−0.0134 (8)	0.0042 (8)

Geometric parameters (Å, º) top

C1—N1	1.327 (3)	C20—C21	1.386 (3)
C1—C2	1.388 (3)	C20—H20	0.9300
C1—H1	0.9300	C21—C22	1.366 (3)
C2—C3	1.362 (3)	C21—H21	0.9300
C2—H2	0.9300	C22—C23	1.402 (3)
C3—C4	1.405 (3)	C22—H22	0.9300
C3—H3A	0.9300	C23—C31	1.405 (3)
C4—C12	1.414 (3)	C23—C24	1.420 (3)
C4—C5	1.426 (3)	C24—N7	1.365 (3)
C5—N3	1.371 (2)	C24—C25	1.384 (3)
C5—C6	1.374 (3)	C25—N8	1.377 (3)
C6—N4	1.371 (3)	C25—C26	1.430 (3)
C6—C7	1.427 (3)	C26—C27	1.399 (3)
C7—C8	1.402 (3)	C26—C30	1.407 (3)
C7—C11	1.414 (3)	C27—C28	1.369 (3)
C8—C9	1.363 (3)	C27—H27	0.9300
C8—H8	0.9300	C28—C29	1.388 (4)
C9—C10	1.390 (3)	C28—H28	0.9300
C9—H9	0.9300	C29—N6	1.319 (3)
C10—N2	1.320 (3)	C29—H29	0.9300
C10—H10	0.9300	C30—N6	1.352 (3)
C11—N2	1.350 (3)	C30—C31	1.468 (3)
C11—C12	1.459 (3)	C31—N5	1.358 (3)
C12—N1	1.359 (3)	C32—N8	1.327 (3)
C13—N4	1.327 (3)	C32—N7	1.365 (3)
C13—N3	1.367 (3)	C32—C33	1.468 (3)
C13—C14	1.472 (3)	C33—C38	1.377 (3)
C14—C19	1.381 (3)	C33—C34	1.380 (3)
C14—C15	1.381 (3)	C34—C35	1.371 (4)
C15—C16	1.377 (3)	C34—H34	0.9300
C15—H15	0.9300	C35—C36	1.370 (4)
C16—C17	1.364 (4)	C35—H35	0.9300
C16—H16	0.9300	C36—C37	1.354 (4)
C17—C18	1.360 (4)	C36—H36	0.9300
C17—H17	0.9300	C37—C38	1.380 (4)
C18—C19	1.381 (3)	C37—H37	0.9300
C18—H18	0.9300	C38—H38	0.9300
C19—H19	0.9300	N3—H3	0.8600
C20—N5	1.328 (3)	N7—H7	0.8600

N1—C1—C2	123.9 (2)	C21—C22—C23	119.0 (2)
N1—C1—H1	118.1	C21—C22—H22	120.5
C2—C1—H1	118.1	C23—C22—H22	120.5
C3—C2—C1	118.9 (2)	C22—C23—C31	118.7 (2)
C3—C2—H2	120.5	C22—C23—C24	124.4 (2)
C1—C2—H2	120.5	C31—C23—C24	116.91 (18)
C2—C3—C4	119.3 (2)	N7—C24—C25	105.51 (18)
C2—C3—H3A	120.3	N7—C24—C23	131.11 (18)
C4—C3—H3A	120.3	C25—C24—C23	123.3 (2)
C3—C4—C12	118.36 (18)	N8—C25—C24	110.69 (19)
C3—C4—C5	124.80 (19)	N8—C25—C26	128.53 (19)
C12—C4—C5	116.80 (18)	C24—C25—C26	120.8 (2)
N3—C5—C6	105.81 (17)	C27—C26—C30	118.2 (2)
N3—C5—C4	130.73 (19)	C27—C26—C25	124.0 (2)
C6—C5—C4	123.36 (19)	C30—C26—C25	117.79 (19)
N4—C6—C5	110.98 (18)	C28—C27—C26	119.0 (2)
N4—C6—C7	128.25 (19)	C28—C27—H27	120.5
C5—C6—C7	120.76 (18)	C26—C27—H27	120.5
C8—C7—C11	118.0 (2)	C27—C28—C29	118.6 (2)
C8—C7—C6	123.79 (19)	C27—C28—H28	120.7
C11—C7—C6	118.21 (19)	C29—C28—H28	120.7
C9—C8—C7	118.9 (2)	N6—C29—C28	124.3 (2)
C9—C8—H8	120.6	N6—C29—H29	117.8
C7—C8—H8	120.6	C28—C29—H29	117.8
C8—C9—C10	119.2 (2)	N6—C30—C26	122.15 (19)
C8—C9—H9	120.4	N6—C30—C31	117.3 (2)
C10—C9—H9	120.4	C26—C30—C31	120.52 (19)
N2—C10—C9	124.0 (2)	N5—C31—C23	121.66 (18)
N2—C10—H10	118.0	N5—C31—C30	117.79 (19)
C9—C10—H10	118.0	C23—C31—C30	120.55 (19)
N2—C11—C7	122.30 (19)	N8—C32—N7	112.31 (19)
N2—C11—C12	117.46 (19)	N8—C32—C33	123.9 (2)
C7—C11—C12	120.21 (18)	N7—C32—C33	123.74 (19)
N1—C12—C4	121.24 (19)	C38—C33—C34	117.9 (2)
N1—C12—C11	118.20 (18)	C38—C33—C32	119.7 (2)
C4—C12—C11	120.53 (18)	C34—C33—C32	122.4 (2)
N4—C13—N3	112.41 (17)	C35—C34—C33	120.9 (3)
N4—C13—C14	123.79 (19)	C35—C34—H34	119.5
N3—C13—C14	123.8 (2)	C33—C34—H34	119.5
C19—C14—C15	118.4 (2)	C36—C35—C34	120.5 (3)
C19—C14—C13	118.8 (2)	C36—C35—H35	119.7
C15—C14—C13	122.9 (2)	C34—C35—H35	119.7
C16—C15—C14	121.1 (3)	C37—C36—C35	119.2 (3)
C16—C15—H15	119.5	C37—C36—H36	120.4
C14—C15—H15	119.5	C35—C36—H36	120.4
C17—C16—C15	119.8 (3)	C36—C37—C38	120.8 (3)
C17—C16—H16	120.1	C36—C37—H37	119.6
C15—C16—H16	120.1	C38—C37—H37	119.6
C18—C17—C16	119.9 (2)	C33—C38—C37	120.7 (3)
C18—C17—H17	120.1	C33—C38—H38	119.7
C16—C17—H17	120.1	C37—C38—H38	119.7
C17—C18—C19	120.9 (3)	C1—N1—C12	118.24 (18)
C17—C18—H18	119.6	C10—N2—C11	117.7 (2)
C19—C18—H18	119.6	C13—N3—C5	106.42 (18)
C14—C19—C18	120.0 (3)	C13—N3—H3	126.8
C14—C19—H19	120.0	C5—N3—H3	126.8
C18—C19—H19	120.0	C13—N4—C6	104.37 (17)
N5—C20—C21	124.2 (2)	C20—N5—C31	117.64 (19)
N5—C20—H20	117.9	C29—N6—C30	117.6 (2)
C21—C20—H20	117.9	C24—N7—C32	107.11 (17)
C22—C21—C20	118.7 (2)	C24—N7—H7	126.4
C22—C21—H21	120.6	C32—N7—H7	126.4
C20—C21—H21	120.6	C32—N8—C25	104.37 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N5ⁱ	0.86	2.10	2.932 (3)	164
N7—H7···N1	0.86	2.12	2.951 (2)	163

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₂N₄
M_r	296.33
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	10.016 (2), 12.210 (2), 12.415 (3)
α, β, γ (°)	89.90 (3), 78.44 (3), 77.96 (3)
V (Å³)	1453.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.975, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	14453, 6587, 3657
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.156, 1.01
No. of reflections	6587
No. of parameters	415
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.20

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N5ⁱ	0.86	2.10	2.932 (3)	164
N7—H7···N1	0.86	2.12	2.951 (2)	163

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors thank the Postdoctoral Foundation of Jiangsu Province (No. 0801010B) for support.

References

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