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

Xi, H.-M.

doi:10.1107/S1600536808029759

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1981

doi:10.1107/S1600536808029759

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

Hong-Min Xi ^a ^*

^aDepartment of Chemistry, College of Chemistry and Biology, Beihua University, Jilin City 132013, People's Republic of China
^*Correspondence e-mail: jlshmx@126.com

(Received 15 September 2008; accepted 16 September 2008; online 20 September 2008)

There are two molecules in the asymmetric unit of the title compound, C₁₉H₁₂N₄. One is almost planar [dihedral angle between the fused-ring system and the phenyl ring = 2.16 (13)°] and one is somewhat twisted [dihedral angle = 13.30 (14)°]. In the crystal, the molecules are linked by N—H⋯N hydrogen bonds to result in chains.

Related literature

For related literature, see Zhang et al. (2008 ); Yin (2008 ).

Experimental

Crystal data

C₁₉H₁₂N₄
M_r = 296.33
Monoclinic, P 2₁ /c
a = 12.3326 (15) Å
b = 12.2334 (15) Å
c = 19.885 (2) Å
β = 104.010 (2)°
V = 2910.9 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.24 × 0.21 × 0.19 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.981, T_max = 0.982
23942 measured reflections
5721 independent reflections
2627 reflections with I > 2σ(I)
R_int = 0.089

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.167
S = 0.97
5721 reflections
415 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N6ⁱ	0.86	2.09	2.932 (4)	165
N8—H8A⋯N2ⁱ	0.86	2.12	2.948 (3)	163
Symmetry code: (i) $[-x+3, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029759/bt2790sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029759/bt2790Isup2.hkl

checkCIF report

Comment top

1,10-Phenanthroline and its derivatives are widely utilized as ligands in metal complexes (Zhang et al., 2008). I report here the crystal structure of the title compound, which was synthesized from 1,10-phenanthroline-5,6-dione. In this compound, all the bond lengths are within normal ranges (Yin, 2008). The asymmetric unit consists of two independent molecules (Fig. 1), which are connected by N—H···N hydrogen bonds to form a one-dimensional chain (Table 1).

Related literature top

For related literature, see Zhang et al. (2008); Yin (2008).

Experimental top

1,10-Phenanthroline-5,6-dione (1.5 mmol) and benzaldehyde (1.5 mmol) were dissolved in CH₃COOHCH₃COONH₄ (1:1) solution (30 ml). The mixture was refluxed for 3 h under argon, after cooling, this mixture was diluted with water and neutralized with concentrated aqueous ammonia, immediately resulting a yellow precipitate, which was washed with water, acetone and diethyl ether respectively. Crystals of the title compound were obtained by recrystallization from dichloromethane.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

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

Crystal data top

C₁₉H₁₂N₄	F(000) = 1232
M_r = 296.33	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5721 reflections
a = 12.3326 (15) Å	θ = 1.1–26.0°
b = 12.2334 (15) Å	µ = 0.08 mm⁻¹
c = 19.885 (2) Å	T = 293 K
β = 104.010 (2)°	Block, pale yellow
V = 2910.9 (6) Å³	0.24 × 0.21 × 0.19 mm
Z = 8

Data collection top

Bruker APEX CCD area-detector diffractometer	5721 independent reflections
Radiation source: fine-focus sealed tube	2627 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.089
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SAINT; Bruker, 1998)	h = −15→15
T_min = 0.981, T_max = 0.982	k = −15→14
23942 measured reflections	l = −24→24

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0719P)²] where P = (F_o² + 2F_c²)/3
5721 reflections	(Δ/σ)_max < 0.001
415 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₉H₁₂N₄	V = 2910.9 (6) Å³
M_r = 296.33	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3326 (15) Å	µ = 0.08 mm⁻¹
b = 12.2334 (15) Å	T = 293 K
c = 19.885 (2) Å	0.24 × 0.21 × 0.19 mm
β = 104.010 (2)°

Data collection top

Bruker APEX CCD area-detector diffractometer	5721 independent reflections
Absorption correction: multi-scan (SAINT; Bruker, 1998)	2627 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.982	R_int = 0.089
23942 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 0.97	Δρ_max = 0.62 e Å⁻³
5721 reflections	Δρ_min = −0.26 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	1.8134 (3)	−0.7259 (3)	1.53329 (17)	0.0535 (9)
H1	1.8713	−0.7628	1.5634	0.064*
C2	1.7966 (3)	−0.6167 (2)	1.54683 (16)	0.0504 (8)
H2	1.8415	−0.5822	1.5853	0.061*
C3	1.7134 (2)	−0.5611 (2)	1.50287 (16)	0.0475 (8)
H3	1.7017	−0.4875	1.5103	0.057*
C4	1.6452 (2)	−0.6157 (2)	1.44615 (15)	0.0400 (7)
C5	1.6667 (2)	−0.7273 (2)	1.43635 (15)	0.0399 (7)
C6	1.5946 (2)	−0.7898 (2)	1.38033 (15)	0.0405 (7)
C7	1.5008 (2)	−0.7402 (2)	1.33678 (15)	0.0423 (7)
C8	1.4329 (3)	−0.8051 (3)	1.28464 (16)	0.0510 (8)
H8	1.3714	−0.7748	1.2537	0.061*
C9	1.4585 (3)	−0.9123 (3)	1.28015 (17)	0.0558 (9)
H9	1.4135	−0.9571	1.2470	0.067*
C10	1.5533 (3)	−0.9541 (3)	1.32599 (18)	0.0567 (9)
H10	1.5704	−1.0274	1.3216	0.068*
C11	1.4801 (2)	−0.6274 (2)	1.34767 (15)	0.0423 (7)
C12	1.5524 (2)	−0.5691 (2)	1.39835 (16)	0.0417 (7)
C13	1.4147 (3)	−0.4650 (2)	1.34191 (16)	0.0465 (8)
C14	1.3452 (3)	−0.3683 (3)	1.32024 (17)	0.0509 (8)
C15	1.2420 (3)	−0.3792 (3)	1.27505 (18)	0.0676 (10)
H15	1.2177	−0.4474	1.2568	0.081*
C16	1.1741 (3)	−0.2880 (4)	1.25679 (19)	0.0840 (13)
H16	1.1044	−0.2959	1.2262	0.101*
C17	1.2078 (4)	−0.1869 (3)	1.2829 (2)	0.0820 (12)
H17	1.1615	−0.1266	1.2701	0.098*
C18	1.3100 (4)	−0.1754 (3)	1.3277 (2)	0.0866 (13)
H18	1.3334	−0.1070	1.3461	0.104*
C19	1.3788 (3)	−0.2654 (3)	1.3460 (2)	0.0755 (12)
H19	1.4488	−0.2567	1.3761	0.091*
C20	1.1864 (3)	−0.9545 (3)	1.14281 (18)	0.0627 (10)
H20	1.2040	−1.0282	1.1500	0.075*
C21	1.1001 (3)	−0.9129 (3)	1.16926 (18)	0.0620 (10)
H21	1.0615	−0.9575	1.1934	0.074*
C22	1.0735 (3)	−0.8046 (3)	1.15866 (17)	0.0549 (9)
H22	1.0172	−0.7741	1.1764	0.066*
C23	1.1315 (2)	−0.7401 (2)	1.12107 (15)	0.0441 (8)
C24	1.2181 (2)	−0.7894 (2)	1.09701 (15)	0.0425 (7)
C25	1.2812 (2)	−0.7264 (2)	1.05692 (15)	0.0421 (7)
C26	1.4170 (3)	−0.7220 (3)	0.99579 (17)	0.0548 (9)
H26	1.4723	−0.7579	0.9797	0.066*
C27	1.3965 (3)	−0.6129 (2)	0.97781 (17)	0.0540 (9)
H27	1.4362	−0.5774	0.9500	0.065*
C28	1.3169 (3)	−0.5593 (2)	1.00190 (16)	0.0486 (8)
H28	1.3023	−0.4860	0.9912	0.058*
C29	1.2573 (2)	−0.6147 (2)	1.04264 (15)	0.0409 (7)
C30	1.1711 (2)	−0.5686 (2)	1.06952 (15)	0.0424 (8)
C31	1.1082 (2)	−0.6270 (2)	1.10553 (15)	0.0429 (7)
C32	1.0428 (2)	−0.4646 (3)	1.09756 (16)	0.0446 (8)
C33	0.9771 (2)	−0.3676 (2)	1.10415 (16)	0.0458 (8)
C34	0.8959 (3)	−0.3745 (3)	1.14149 (18)	0.0628 (10)
H34	0.8819	−0.4411	1.1603	0.075*
C35	0.8357 (3)	−0.2833 (3)	1.1510 (2)	0.0745 (11)
H35	0.7819	−0.2887	1.1765	0.089*
C36	0.8546 (3)	−0.1844 (3)	1.1231 (2)	0.0762 (12)
H36	0.8143	−0.1228	1.1299	0.091*
C37	0.9327 (3)	−0.1776 (3)	1.0856 (2)	0.0741 (11)
H37	0.9449	−0.1111	1.0660	0.089*
C38	0.9945 (3)	−0.2677 (3)	1.07615 (18)	0.0614 (9)
H38	1.0482	−0.2612	1.0507	0.074*
N1	1.6202 (2)	−0.8969 (2)	1.37510 (13)	0.0491 (7)
N2	1.7522 (2)	−0.78066 (19)	1.48026 (13)	0.0470 (7)
N3	1.5101 (2)	−0.46462 (19)	1.39421 (13)	0.0499 (7)
H3A	1.5380	−0.4098	1.4196	0.060*
N4	1.3927 (2)	−0.5633 (2)	1.31277 (13)	0.0501 (7)
N5	1.2449 (2)	−0.8967 (2)	1.10833 (14)	0.0530 (7)
N6	1.3630 (2)	−0.7781 (2)	1.03437 (13)	0.0504 (7)
N7	1.0279 (2)	−0.5624 (2)	1.12287 (13)	0.0488 (7)
N8	1.12765 (19)	−0.46471 (18)	1.06446 (12)	0.0439 (6)
H8A	1.1498	−0.4099	1.0442	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.051 (2)	0.051 (2)	0.053 (2)	0.0050 (17)	0.0021 (18)	−0.0024 (17)
C2	0.050 (2)	0.048 (2)	0.049 (2)	−0.0014 (17)	0.0046 (17)	−0.0064 (16)
C3	0.0459 (19)	0.0405 (18)	0.056 (2)	−0.0025 (15)	0.0121 (17)	−0.0003 (16)
C4	0.0371 (17)	0.0367 (18)	0.0460 (19)	−0.0029 (14)	0.0099 (15)	0.0026 (15)
C5	0.0350 (17)	0.0377 (17)	0.0485 (19)	0.0002 (14)	0.0130 (15)	0.0009 (15)
C6	0.0411 (18)	0.0381 (18)	0.0437 (19)	−0.0043 (14)	0.0133 (16)	−0.0010 (14)
C7	0.0394 (18)	0.049 (2)	0.0398 (19)	−0.0057 (15)	0.0126 (15)	−0.0012 (15)
C8	0.048 (2)	0.052 (2)	0.052 (2)	−0.0050 (16)	0.0106 (17)	−0.0021 (17)
C9	0.054 (2)	0.054 (2)	0.058 (2)	−0.0138 (17)	0.0112 (19)	−0.0162 (17)
C10	0.062 (2)	0.048 (2)	0.061 (2)	−0.0018 (18)	0.016 (2)	−0.0136 (17)
C11	0.0397 (18)	0.0403 (18)	0.048 (2)	−0.0015 (15)	0.0126 (16)	0.0049 (15)
C12	0.0385 (17)	0.0366 (18)	0.050 (2)	0.0002 (15)	0.0111 (16)	0.0039 (15)
C13	0.0422 (19)	0.045 (2)	0.052 (2)	0.0008 (16)	0.0107 (17)	0.0044 (16)
C14	0.044 (2)	0.053 (2)	0.056 (2)	0.0071 (17)	0.0129 (17)	0.0060 (17)
C15	0.063 (2)	0.073 (3)	0.059 (2)	0.018 (2)	0.000 (2)	−0.008 (2)
C16	0.068 (3)	0.101 (3)	0.070 (3)	0.032 (3)	−0.007 (2)	−0.004 (3)
C17	0.083 (3)	0.070 (3)	0.088 (3)	0.033 (2)	0.011 (3)	0.014 (2)
C18	0.075 (3)	0.055 (3)	0.121 (4)	0.015 (2)	0.006 (3)	0.006 (2)
C19	0.051 (2)	0.054 (2)	0.113 (3)	0.0055 (19)	0.002 (2)	0.010 (2)
C20	0.066 (2)	0.042 (2)	0.082 (3)	−0.0017 (18)	0.022 (2)	0.0144 (18)
C21	0.058 (2)	0.060 (2)	0.074 (3)	−0.0027 (18)	0.027 (2)	0.0179 (19)
C22	0.050 (2)	0.054 (2)	0.064 (2)	−0.0010 (17)	0.0192 (18)	0.0095 (17)
C23	0.0398 (18)	0.0437 (19)	0.048 (2)	−0.0021 (15)	0.0099 (16)	0.0029 (15)
C24	0.0448 (18)	0.0329 (17)	0.049 (2)	−0.0007 (14)	0.0094 (16)	0.0009 (14)
C25	0.0377 (17)	0.0419 (18)	0.0472 (19)	−0.0007 (14)	0.0112 (15)	−0.0022 (15)
C26	0.053 (2)	0.051 (2)	0.066 (2)	0.0059 (17)	0.0263 (19)	−0.0033 (18)
C27	0.057 (2)	0.044 (2)	0.070 (2)	−0.0008 (16)	0.0334 (19)	0.0021 (17)
C28	0.054 (2)	0.0377 (18)	0.057 (2)	−0.0006 (15)	0.0200 (18)	−0.0022 (15)
C29	0.0383 (17)	0.0378 (18)	0.047 (2)	−0.0013 (14)	0.0105 (15)	−0.0022 (14)
C30	0.0387 (17)	0.0376 (18)	0.051 (2)	−0.0024 (14)	0.0116 (16)	−0.0017 (14)
C31	0.0387 (17)	0.0407 (18)	0.0492 (19)	0.0026 (15)	0.0102 (15)	−0.0006 (15)
C32	0.0407 (18)	0.049 (2)	0.047 (2)	−0.0007 (15)	0.0164 (16)	−0.0027 (16)
C33	0.0369 (18)	0.047 (2)	0.052 (2)	0.0052 (15)	0.0083 (16)	−0.0033 (16)
C34	0.058 (2)	0.059 (2)	0.076 (3)	0.0065 (19)	0.027 (2)	0.0014 (19)
C35	0.062 (2)	0.084 (3)	0.085 (3)	0.016 (2)	0.032 (2)	−0.003 (2)
C36	0.075 (3)	0.066 (3)	0.091 (3)	0.029 (2)	0.025 (2)	−0.009 (2)
C37	0.076 (3)	0.055 (2)	0.096 (3)	0.020 (2)	0.031 (3)	0.009 (2)
C38	0.059 (2)	0.050 (2)	0.079 (3)	0.0112 (18)	0.027 (2)	0.0061 (19)
N1	0.0507 (16)	0.0428 (16)	0.0552 (18)	0.0009 (13)	0.0153 (14)	−0.0079 (13)
N2	0.0444 (15)	0.0413 (15)	0.0538 (17)	0.0008 (13)	0.0091 (14)	−0.0011 (13)
N3	0.0468 (16)	0.0396 (16)	0.0610 (18)	0.0006 (13)	0.0083 (15)	0.0011 (13)
N4	0.0453 (16)	0.0502 (17)	0.0529 (17)	0.0029 (13)	0.0081 (14)	0.0054 (14)
N5	0.0517 (16)	0.0394 (16)	0.0678 (19)	0.0027 (13)	0.0144 (15)	0.0081 (13)
N6	0.0471 (16)	0.0431 (16)	0.0648 (19)	0.0005 (13)	0.0213 (15)	0.0005 (13)
N7	0.0453 (16)	0.0458 (16)	0.0578 (18)	0.0015 (13)	0.0171 (14)	0.0024 (13)
N8	0.0429 (15)	0.0357 (15)	0.0558 (17)	0.0044 (12)	0.0171 (14)	0.0027 (12)

Geometric parameters (Å, º) top

C1—N2	1.321 (4)	C20—C21	1.393 (4)
C1—C2	1.388 (4)	C20—H20	0.9300
C1—H1	0.9300	C21—C22	1.369 (4)
C2—C3	1.359 (4)	C21—H21	0.9300
C2—H2	0.9300	C22—C23	1.397 (4)
C3—C4	1.402 (4)	C22—H22	0.9300
C3—H3	0.9300	C23—C24	1.407 (4)
C4—C5	1.413 (4)	C23—C31	1.432 (4)
C4—C12	1.419 (4)	C24—N5	1.359 (3)
C5—N2	1.362 (3)	C24—C25	1.461 (4)
C5—C6	1.462 (4)	C25—N6	1.356 (3)
C6—N1	1.357 (3)	C25—C29	1.412 (4)
C6—C7	1.405 (4)	C26—N6	1.323 (4)
C7—C8	1.409 (4)	C26—C27	1.389 (4)
C7—C11	1.429 (4)	C26—H26	0.9300
C8—C9	1.357 (4)	C27—C28	1.361 (4)
C8—H8	0.9300	C27—H27	0.9300
C9—C10	1.394 (4)	C28—C29	1.394 (4)
C9—H9	0.9300	C28—H28	0.9300
C10—N1	1.317 (4)	C29—C30	1.418 (4)
C10—H10	0.9300	C30—N8	1.374 (3)
C11—C12	1.373 (4)	C30—C31	1.376 (4)
C11—N4	1.377 (3)	C31—N7	1.375 (3)
C12—N3	1.375 (3)	C32—N7	1.327 (3)
C13—N4	1.334 (3)	C32—N8	1.364 (3)
C13—N3	1.368 (4)	C32—C33	1.462 (4)
C13—C14	1.464 (4)	C33—C38	1.380 (4)
C14—C15	1.375 (4)	C33—C34	1.386 (4)
C14—C19	1.384 (4)	C34—C35	1.378 (4)
C15—C16	1.390 (5)	C34—H34	0.9300
C15—H15	0.9300	C35—C36	1.374 (5)
C16—C17	1.365 (5)	C35—H35	0.9300
C16—H16	0.9300	C36—C37	1.356 (5)
C17—C18	1.364 (5)	C36—H36	0.9300
C17—H17	0.9300	C37—C38	1.378 (4)
C18—C19	1.385 (4)	C37—H37	0.9300
C18—H18	0.9300	C38—H38	0.9300
C19—H19	0.9300	N3—H3A	0.8600
C20—N5	1.315 (4)	N8—H8A	0.8600

N2—C1—C2	124.0 (3)	C21—C22—C23	119.7 (3)
N2—C1—H1	118.0	C21—C22—H22	120.2
C2—C1—H1	118.0	C23—C22—H22	120.2
C3—C2—C1	118.8 (3)	C22—C23—C24	118.0 (3)
C3—C2—H2	120.6	C22—C23—C31	124.0 (3)
C1—C2—H2	120.6	C24—C23—C31	118.0 (3)
C2—C3—C4	119.4 (3)	N5—C24—C23	122.1 (3)
C2—C3—H3	120.3	N5—C24—C25	117.4 (3)
C4—C3—H3	120.3	C23—C24—C25	120.5 (3)
C3—C4—C5	118.4 (3)	N6—C25—C29	121.4 (3)
C3—C4—C12	125.2 (3)	N6—C25—C24	118.1 (3)
C5—C4—C12	116.4 (3)	C29—C25—C24	120.5 (3)
N2—C5—C4	121.1 (3)	N6—C26—C27	124.1 (3)
N2—C5—C6	118.1 (3)	N6—C26—H26	117.9
C4—C5—C6	120.7 (3)	C27—C26—H26	117.9
N1—C6—C7	122.9 (3)	C28—C27—C26	118.3 (3)
N1—C6—C5	117.0 (3)	C28—C27—H27	120.8
C7—C6—C5	120.1 (3)	C26—C27—H27	120.8
C6—C7—C8	117.6 (3)	C27—C28—C29	119.8 (3)
C6—C7—C11	118.4 (3)	C27—C28—H28	120.1
C8—C7—C11	124.0 (3)	C29—C28—H28	120.1
C9—C8—C7	119.1 (3)	C28—C29—C25	118.3 (3)
C9—C8—H8	120.4	C28—C29—C30	125.1 (3)
C7—C8—H8	120.4	C25—C29—C30	116.6 (3)
C8—C9—C10	118.9 (3)	N8—C30—C31	105.0 (3)
C8—C9—H9	120.5	N8—C30—C29	130.9 (3)
C10—C9—H9	120.5	C31—C30—C29	124.0 (3)
N1—C10—C9	124.4 (3)	N7—C31—C30	111.3 (3)
N1—C10—H10	117.8	N7—C31—C23	128.4 (3)
C9—C10—H10	117.8	C30—C31—C23	120.3 (3)
C12—C11—N4	111.4 (3)	N7—C32—N8	112.1 (3)
C12—C11—C7	120.3 (3)	N7—C32—C33	124.5 (3)
N4—C11—C7	128.3 (3)	N8—C32—C33	123.4 (3)
C11—C12—N3	105.6 (3)	C38—C33—C34	118.2 (3)
C11—C12—C4	123.9 (3)	C38—C33—C32	122.6 (3)
N3—C12—C4	130.3 (3)	C34—C33—C32	119.1 (3)
N4—C13—N3	112.4 (3)	C35—C34—C33	120.4 (3)
N4—C13—C14	123.9 (3)	C35—C34—H34	119.8
N3—C13—C14	123.8 (3)	C33—C34—H34	119.8
C15—C14—C19	118.5 (3)	C36—C35—C34	120.6 (3)
C15—C14—C13	119.8 (3)	C36—C35—H35	119.7
C19—C14—C13	121.6 (3)	C34—C35—H35	119.7
C14—C15—C16	119.8 (4)	C37—C36—C35	119.2 (3)
C14—C15—H15	120.1	C37—C36—H36	120.4
C16—C15—H15	120.1	C35—C36—H36	120.4
C17—C16—C15	121.3 (4)	C36—C37—C38	121.1 (4)
C17—C16—H16	119.4	C36—C37—H37	119.5
C15—C16—H16	119.4	C38—C37—H37	119.5
C18—C17—C16	119.4 (3)	C37—C38—C33	120.5 (3)
C18—C17—H17	120.3	C37—C38—H38	119.7
C16—C17—H17	120.3	C33—C38—H38	119.7
C17—C18—C19	120.0 (4)	C10—N1—C6	117.0 (3)
C17—C18—H18	120.0	C1—N2—C5	118.2 (3)
C19—C18—H18	120.0	C13—N3—C12	106.6 (2)
C14—C19—C18	121.1 (4)	C13—N3—H3A	126.7
C14—C19—H19	119.4	C12—N3—H3A	126.7
C18—C19—H19	119.4	C13—N4—C11	104.0 (3)
N5—C20—C21	124.5 (3)	C20—N5—C24	117.6 (3)
N5—C20—H20	117.8	C26—N6—C25	118.0 (3)
C21—C20—H20	117.8	C32—N7—C31	104.4 (2)
C22—C21—C20	118.1 (3)	C32—N8—C30	107.2 (2)
C22—C21—H21	120.9	C32—N8—H8A	126.4
C20—C21—H21	120.9	C30—N8—H8A	126.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N6ⁱ	0.86	2.09	2.932 (4)	165
N8—H8A···N2ⁱ	0.86	2.12	2.948 (3)	163

Symmetry code: (i) −x+3, y+1/2, −z+5/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₂N₄
M_r	296.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.3326 (15), 12.2334 (15), 19.885 (2)
β (°)	104.010 (2)
V (Å³)	2910.9 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.24 × 0.21 × 0.19

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SAINT; Bruker, 1998)
T_min, T_max	0.981, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	23942, 5721, 2627
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.167, 0.97
No. of reflections	5721
No. of parameters	415
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.26

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 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—H3A···N6ⁱ	0.86	2.09	2.932 (4)	165.0
N8—H8A···N2ⁱ	0.86	2.12	2.948 (3)	162.5

Symmetry code: (i) −x+3, y+1/2, −z+5/2.

Acknowledgements

The author thanks Beihua University for supporting this work.

References

Bruker (1998). SMART,SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yin, G.-Q. (2008). Acta Cryst. E64, o1236. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, W.-Z., Li, L. & Xiao, Y.-H. (2008). Acta Cryst. E64, o1331. Web of Science CSD CrossRef IUCr Journals Google Scholar