2-(4-Methyl­phen­yl)-1H-imidazo[4,5-f][1,10]phenanthroline

Ma, L.; Lu, L.; Zhu, M.

doi:10.1107/S1600536811008853

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages o864-o865

doi:10.1107/S1600536811008853

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2-(4-Methylphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline

Ling Ma,^a Liping Lu ^a and Miaoli Zhu ^a ^*

^aInstitute of Molecular Science, Key Laboratory of Chemical Biology and Molecular, Engineering of the Education Ministry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China
^*Correspondence e-mail: miaoli@sxu.edu.cn

(Received 5 March 2011; accepted 8 March 2011; online 12 March 2011)

In the title compound, C₂₀H₁₄N₄, all the non-H atoms are roughly coplanar with an r.m.s. deviation of 0.0776 Å. In the crystal, molecules are linked by N—H⋯N hydrogen bonds, forming chains along the ( $[\overline a + \overline b]$ ). The chains are connected by intermolecular C—H⋯N hydrogen bonds and π–π stacking interactions between inversion-related phenanthroline, imidazole and phenyl rings with centroid–centroid distances in the range 3.777 (1)–3.905 (1) Å.

Related literature

For the biological activity of complexes of metal ions with 1,10-phenanthroline and its derivatives, see: Gao et al. (2009 ); Lu et al. (2003 ); Yuan et al. (2009 , 2010 ); Chen et al. (2010 ). For aromatic π–π stacking interactions in related structures, see: Lu et al. (2004a ,b ,c ,d ); Ma et al. (2010 ); Ye et al. (2005 ); Zhang et al. (2005 ).

Experimental

Crystal data

C₂₀H₁₄N₄
M_r = 310.35
Monoclinic, P 2₁ /n
a = 9.1609 (8) Å
b = 15.5398 (13) Å
c = 11.725 (1) Å
β = 108.892 (1)°
V = 1579.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.976, T_max = 0.984
10917 measured reflections
2790 independent reflections
2182 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.107
S = 1.05
2790 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N1ⁱ	0.908 (19)	2.106 (19)	3.0131 (19)	176.0 (17)
C1—H1⋯N3ⁱⁱ	0.93	2.57	3.479 (2)	165
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008853/lw2058sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008853/lw2058Isup2.hkl

checkCIF report

Comment top

We have been interested in the bioactivity research of the complexes of metal ions with 1,10-phenanthroline and its derivatives, such as nuclease activity of mono (1,10-phenanthroline) copper complex (Lu et al., 2003), protein tyrosine phosphatases inhibition activities of oxovanadium complexes with polypyridyl derivatives (Yuan et al., 2009,2010; Gao et al., 2009), selective OFF-ON fluorescent sensor for zinc in aqueous solution and living cells (Chen et al., 2010). As we know, 1,10-phenanthroline and its derivatives, 2,2'-bipyridyl-like, are good planar ligands in metal-organic compounds, in which there are strong π–π stacking interactions (Ye et al., 2005; Lu et al., 2004a, 2004b, 2004c; 2004d; Zhang et al., 2005; Ma et al., 2010). We report here the structure of (I) (Fig. 1), which was synthesized from 1,10-Phenanthroline-5,6-dione and 4-methylbenzaldehyde. All non-hydrogen atoms of (I) are coplanar with a 0.0776 value of r.m.s. deviation of fitted atoms. The molecules are linked by N—H···N hydrogen bonds to form one-dimensional chains (Fig. 2), and the chains are connected by intermolecular C—H···N hydrogen bonds and π–π stacking interactions between inversion related phenanthroline and phenyl rings to complete the hydrogen bonding network in the crystal structure. The stacking distance π–π is in the range of 3.777 (1) to 3.905 (1) Å, namely Cg1···Cg3ⁱ 3.905 (1), Cg2···Cg3ⁱ 3.867 (1), Cg3···Cg3ⁱⁱ 3.777 (1) Å. Cg1, Cg2, and Cg3 for the centroids of rings N1/C1—C5, C4—C7/C11/C12, C14—C19, respectively, symmetry codes i 1 - x,-y,1 - z; ii 2 - x,-y,1 - z.

Related literature top

For the biological activity of complexes of metal ions with 1,10-phenanthroline and its derivatives, see: Gao et al. (2009); Lu et al. (2003); Yuan et al. (2009, 2010); Chen et al. (2010); For aromatic π–π stacking interactions in related structures, see: Lu et al. (2004a,b,c,d); Ma et al. (2010); Ye et al. (2005); Zhang et al. (2005).

Experimental top

1,10-Phenanthroline-5,6-dione (1.2 mmol), 4-methylbenzaldehyde (1.0 mmol), and ammonium acetate (4 mmol) were added in 20 ml of glacial acetic acid with a constant of stirring, and the mixture was refluxed for 2 h. When the reaction was cooled to room temperature, poured in 20 ml of water. The solution was neutralized with ammonia to pH 7. The precipitate was filtered off and recrystallized from methanol solution to give (I) for X-ray diffraction at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The views of the structures of (I) with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. One-dimensional chain of (I) via N—H···N hydrogen bonds, dotted lines for hydrogen bonds.

2-(4-Methylphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline top

Crystal data top

C₂₀H₁₄N₄	F(000) = 648
M_r = 310.35	D_x = 1.305 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4474 reflections
a = 9.1609 (8) Å	θ = 2.5–27.4°
b = 15.5398 (13) Å	µ = 0.08 mm⁻¹
c = 11.725 (1) Å	T = 298 K
β = 108.892 (1)°	Block, yellow
V = 1579.2 (2) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	2790 independent reflections
Radiation source: fine-focus sealed tube	2182 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −10→10
T_min = 0.976, T_max = 0.984	k = −18→18
10917 measured reflections	l = −13→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.047P)² + 0.4106P] where P = (F_o² + 2F_c²)/3
2790 reflections	(Δ/σ)_max = 0.001
222 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₀H₁₄N₄	V = 1579.2 (2) Å³
M_r = 310.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.1609 (8) Å	µ = 0.08 mm⁻¹
b = 15.5398 (13) Å	T = 298 K
c = 11.725 (1) Å	0.30 × 0.20 × 0.20 mm
β = 108.892 (1)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	2790 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2182 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.984	R_int = 0.021
10917 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.19 e Å⁻³
2790 reflections	Δρ_min = −0.16 e Å⁻³
222 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	0.1494 (2)	0.34388 (11)	0.29392 (16)	0.0569 (5)
H1	0.0796	0.3893	0.2775	0.068*
C2	0.2314 (2)	0.32622 (12)	0.41361 (15)	0.0600 (5)
H2	0.2142	0.3582	0.4751	0.072*
C3	0.3377 (2)	0.26132 (11)	0.43997 (14)	0.0497 (4)
H3	0.3958	0.2495	0.5195	0.060*
C4	0.35793 (17)	0.21310 (9)	0.34572 (13)	0.0394 (4)
C5	0.26563 (18)	0.23316 (10)	0.22634 (13)	0.0413 (4)
C6	0.27420 (18)	0.18067 (10)	0.12531 (13)	0.0424 (4)
C7	0.37132 (17)	0.10795 (10)	0.14623 (13)	0.0405 (4)
C8	0.3685 (2)	0.05668 (11)	0.04748 (14)	0.0506 (4)
H8	0.4290	0.0073	0.0587	0.061*
C9	0.2767 (2)	0.07936 (12)	−0.06532 (15)	0.0607 (5)
H9	0.2740	0.0464	−0.1321	0.073*
C10	0.1872 (2)	0.15308 (12)	−0.07761 (15)	0.0635 (5)
H10	0.1256	0.1686	−0.1548	0.076*
C11	0.46288 (17)	0.14274 (10)	0.36043 (13)	0.0386 (4)
C12	0.46786 (17)	0.09098 (10)	0.26710 (13)	0.0390 (4)
C13	0.63601 (17)	0.04011 (10)	0.42481 (13)	0.0415 (4)
C14	0.76079 (17)	−0.01205 (10)	0.50460 (13)	0.0433 (4)
C15	0.8293 (2)	−0.07558 (12)	0.45554 (16)	0.0549 (5)
H15	0.7935	−0.0854	0.3728	0.066*
C16	0.9495 (2)	−0.12424 (13)	0.52785 (17)	0.0615 (5)
H16	0.9942	−0.1658	0.4926	0.074*
C17	1.0053 (2)	−0.11301 (13)	0.65087 (16)	0.0567 (5)
C18	0.9361 (2)	−0.05052 (13)	0.69982 (16)	0.0600 (5)
H18	0.9709	−0.0419	0.7828	0.072*
C19	0.8162 (2)	−0.00045 (12)	0.62845 (15)	0.0538 (4)
H19	0.7725	0.0414	0.6639	0.065*
C20	1.1369 (2)	−0.16699 (15)	0.7291 (2)	0.0798 (7)
H20A	1.2040	−0.1317	0.7914	0.120*
H20B	1.1938	−0.1907	0.6806	0.120*
H20C	1.0966	−0.2129	0.7649	0.120*
N1	0.16445 (16)	0.29995 (9)	0.20174 (12)	0.0501 (4)
N2	0.18375 (17)	0.20271 (9)	0.01305 (12)	0.0560 (4)
N3	0.57503 (14)	0.02646 (8)	0.30708 (11)	0.0433 (3)
N4	0.57054 (15)	0.10950 (8)	0.46160 (11)	0.0416 (3)
H4	0.603 (2)	0.1350 (12)	0.5353 (17)	0.062 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0703 (12)	0.0485 (10)	0.0497 (10)	0.0146 (9)	0.0165 (9)	−0.0020 (8)
C2	0.0797 (13)	0.0563 (11)	0.0439 (10)	0.0147 (10)	0.0200 (9)	−0.0059 (8)
C3	0.0604 (10)	0.0491 (10)	0.0365 (8)	0.0031 (8)	0.0114 (7)	−0.0023 (7)
C4	0.0447 (8)	0.0365 (8)	0.0354 (8)	−0.0045 (7)	0.0107 (6)	−0.0015 (6)
C5	0.0469 (9)	0.0372 (8)	0.0377 (8)	−0.0005 (7)	0.0109 (7)	0.0004 (7)
C6	0.0481 (9)	0.0423 (9)	0.0338 (8)	0.0009 (7)	0.0089 (7)	0.0007 (7)
C7	0.0453 (9)	0.0412 (9)	0.0350 (8)	−0.0010 (7)	0.0130 (7)	0.0015 (6)
C8	0.0608 (10)	0.0507 (10)	0.0394 (9)	0.0100 (8)	0.0151 (8)	−0.0014 (7)
C9	0.0787 (13)	0.0637 (12)	0.0359 (9)	0.0129 (10)	0.0132 (8)	−0.0062 (8)
C10	0.0787 (13)	0.0678 (12)	0.0337 (9)	0.0174 (10)	0.0041 (8)	−0.0004 (8)
C11	0.0414 (8)	0.0388 (8)	0.0333 (8)	−0.0042 (7)	0.0089 (6)	0.0016 (6)
C12	0.0409 (8)	0.0391 (8)	0.0356 (8)	−0.0011 (7)	0.0104 (6)	0.0019 (6)
C13	0.0436 (8)	0.0417 (9)	0.0386 (8)	−0.0032 (7)	0.0127 (7)	0.0035 (7)
C14	0.0424 (8)	0.0460 (9)	0.0404 (8)	−0.0031 (7)	0.0120 (7)	0.0083 (7)
C15	0.0595 (11)	0.0585 (11)	0.0448 (9)	0.0087 (9)	0.0140 (8)	0.0092 (8)
C16	0.0611 (11)	0.0623 (12)	0.0620 (12)	0.0133 (9)	0.0213 (9)	0.0146 (9)
C17	0.0461 (9)	0.0642 (12)	0.0578 (11)	0.0003 (9)	0.0139 (8)	0.0233 (9)
C18	0.0540 (10)	0.0757 (13)	0.0432 (10)	−0.0034 (9)	0.0060 (8)	0.0141 (9)
C19	0.0533 (10)	0.0617 (11)	0.0443 (9)	0.0007 (8)	0.0126 (8)	0.0055 (8)
C20	0.0587 (12)	0.0927 (16)	0.0806 (15)	0.0122 (11)	0.0124 (11)	0.0390 (13)
N1	0.0613 (9)	0.0434 (8)	0.0418 (8)	0.0089 (7)	0.0114 (6)	0.0003 (6)
N2	0.0698 (10)	0.0544 (9)	0.0355 (7)	0.0137 (7)	0.0054 (7)	0.0003 (6)
N3	0.0457 (7)	0.0438 (8)	0.0379 (7)	0.0023 (6)	0.0099 (6)	0.0027 (6)
N4	0.0463 (7)	0.0417 (8)	0.0327 (7)	−0.0028 (6)	0.0070 (6)	−0.0001 (6)

Geometric parameters (Å, º) top

C1—N1	1.323 (2)	C11—C12	1.371 (2)
C1—C2	1.388 (2)	C11—N4	1.3744 (19)
C1—H1	0.9300	C12—N3	1.3751 (19)
C2—C3	1.366 (2)	C13—N3	1.3278 (19)
C2—H2	0.9300	C13—N4	1.370 (2)
C3—C4	1.396 (2)	C13—C14	1.465 (2)
C3—H3	0.9300	C14—C19	1.386 (2)
C4—C5	1.416 (2)	C14—C15	1.390 (2)
C4—C11	1.429 (2)	C15—C16	1.378 (2)
C5—N1	1.359 (2)	C15—H15	0.9300
C5—C6	1.461 (2)	C16—C17	1.376 (3)
C6—N2	1.3528 (19)	C16—H16	0.9300
C6—C7	1.410 (2)	C17—C18	1.382 (3)
C7—C8	1.399 (2)	C17—C20	1.511 (2)
C7—C12	1.431 (2)	C18—C19	1.384 (2)
C8—C9	1.364 (2)	C18—H18	0.9300
C8—H8	0.9300	C19—H19	0.9300
C9—C10	1.389 (3)	C20—H20A	0.9600
C9—H9	0.9300	C20—H20B	0.9600
C10—N2	1.322 (2)	C20—H20C	0.9600
C10—H10	0.9300	N4—H4	0.908 (19)

N1—C1—C2	123.95 (16)	N3—C12—C7	128.03 (13)
N1—C1—H1	118.0	N3—C13—N4	111.93 (13)
C2—C1—H1	118.0	N3—C13—C14	123.65 (14)
C3—C2—C1	119.18 (16)	N4—C13—C14	124.41 (14)
C3—C2—H2	120.4	C19—C14—C15	117.68 (15)
C1—C2—H2	120.4	C19—C14—C13	122.85 (16)
C2—C3—C4	118.99 (15)	C15—C14—C13	119.47 (14)
C2—C3—H3	120.5	C16—C15—C14	120.86 (17)
C4—C3—H3	120.5	C16—C15—H15	119.6
C3—C4—C5	118.32 (14)	C14—C15—H15	119.6
C3—C4—C11	124.86 (14)	C17—C16—C15	121.78 (19)
C5—C4—C11	116.79 (13)	C17—C16—H16	119.1
N1—C5—C4	121.73 (14)	C15—C16—H16	119.1
N1—C5—C6	117.80 (13)	C16—C17—C18	117.37 (16)
C4—C5—C6	120.46 (14)	C16—C17—C20	121.20 (19)
N2—C6—C7	121.69 (14)	C18—C17—C20	121.43 (18)
N2—C6—C5	118.08 (14)	C17—C18—C19	121.64 (17)
C7—C6—C5	120.20 (13)	C17—C18—H18	119.2
C8—C7—C6	118.11 (14)	C19—C18—H18	119.2
C8—C7—C12	123.68 (14)	C18—C19—C14	120.66 (18)
C6—C7—C12	118.22 (13)	C18—C19—H19	119.7
C9—C8—C7	119.71 (16)	C14—C19—H19	119.7
C9—C8—H8	120.1	C17—C20—H20A	109.5
C7—C8—H8	120.1	C17—C20—H20B	109.5
C8—C9—C10	118.15 (16)	H20A—C20—H20B	109.5
C8—C9—H9	120.9	C17—C20—H20C	109.5
C10—C9—H9	120.9	H20A—C20—H20C	109.5
N2—C10—C9	124.39 (16)	H20B—C20—H20C	109.5
N2—C10—H10	117.8	C1—N1—C5	117.73 (14)
C9—C10—H10	117.8	C10—N2—C6	117.91 (15)
C12—C11—N4	105.57 (13)	C13—N3—C12	104.57 (13)
C12—C11—C4	123.21 (13)	C13—N4—C11	106.80 (13)
N4—C11—C4	131.17 (14)	C13—N4—H4	127.0 (12)
C11—C12—N3	111.12 (13)	C11—N4—H4	125.3 (12)
C11—C12—C7	120.85 (14)

N1—C1—C2—C3	1.8 (3)	C8—C7—C12—N3	2.6 (3)
C1—C2—C3—C4	−1.7 (3)	C6—C7—C12—N3	−177.08 (14)
C2—C3—C4—C5	−0.6 (2)	N3—C13—C14—C19	−175.68 (15)
C2—C3—C4—C11	−178.91 (16)	N4—C13—C14—C19	5.7 (2)
C3—C4—C5—N1	3.1 (2)	N3—C13—C14—C15	5.1 (2)
C11—C4—C5—N1	−178.52 (14)	N4—C13—C14—C15	−173.46 (15)
C3—C4—C5—C6	−175.51 (14)	C19—C14—C15—C16	−0.9 (3)
C11—C4—C5—C6	2.9 (2)	C13—C14—C15—C16	178.34 (16)
N1—C5—C6—N2	1.5 (2)	C14—C15—C16—C17	0.9 (3)
C4—C5—C6—N2	−179.89 (14)	C15—C16—C17—C18	−0.1 (3)
N1—C5—C6—C7	−176.74 (14)	C15—C16—C17—C20	179.85 (17)
C4—C5—C6—C7	1.9 (2)	C16—C17—C18—C19	−0.5 (3)
N2—C6—C7—C8	−2.1 (2)	C20—C17—C18—C19	179.49 (17)
C5—C6—C7—C8	176.11 (15)	C17—C18—C19—C14	0.5 (3)
N2—C6—C7—C12	177.60 (14)	C15—C14—C19—C18	0.3 (3)
C5—C6—C7—C12	−4.2 (2)	C13—C14—C19—C18	−178.97 (15)
C6—C7—C8—C9	1.9 (3)	C2—C1—N1—C5	0.6 (3)
C12—C7—C8—C9	−177.75 (16)	C4—C5—N1—C1	−3.0 (2)
C7—C8—C9—C10	−0.6 (3)	C6—C5—N1—C1	175.60 (15)
C8—C9—C10—N2	−0.6 (3)	C9—C10—N2—C6	0.5 (3)
C3—C4—C11—C12	172.70 (15)	C7—C6—N2—C10	0.9 (3)
C5—C4—C11—C12	−5.6 (2)	C5—C6—N2—C10	−177.34 (17)
C3—C4—C11—N4	−4.5 (3)	N4—C13—N3—C12	1.02 (17)
C5—C4—C11—N4	177.23 (15)	C14—C13—N3—C12	−177.72 (14)
N4—C11—C12—N3	0.13 (17)	C11—C12—N3—C13	−0.70 (17)
C4—C11—C12—N3	−177.65 (13)	C7—C12—N3—C13	178.22 (15)
N4—C11—C12—C7	−178.88 (13)	N3—C13—N4—C11	−0.97 (17)
C4—C11—C12—C7	3.3 (2)	C14—C13—N4—C11	177.76 (14)
C8—C7—C12—C11	−178.62 (15)	C12—C11—N4—C13	0.48 (16)
C6—C7—C12—C11	1.7 (2)	C4—C11—N4—C13	178.01 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N1ⁱ	0.908 (19)	2.106 (19)	3.0131 (19)	176.0 (17)
C1—H1···N3ⁱⁱ	0.93	2.57	3.479 (2)	165

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄N₄
M_r	310.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.1609 (8), 15.5398 (13), 11.725 (1)
β (°)	108.892 (1)
V (Å³)	1579.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.976, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	10917, 2790, 2182
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.107, 1.05
No. of reflections	2790
No. of parameters	222
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and SHELXTL/PC (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N1ⁱ	0.908 (19)	2.106 (19)	3.0131 (19)	176.0 (17)
C1—H1···N3ⁱⁱ	0.93	2.57	3.479 (2)	165

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

Acknowledgements

The authors acknowledge the National Natural Science Foundation of China (grant No. 20471033), the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry (20093602), the Provincial Natural Science Foundation of Shanxi Province (grant No. 2010011011–2) and the Overseas Returned Scholar Foundation of Shanxi Province (200808) for financial support.

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