4,6-Dimethyl-2-(naphthalen-1-yl)pyrimidine

Zhang, X.-X.; Zhu, D.-Y.; Hao, X.-Q.; Dong, X.-M.; Song, M.-P.

doi:10.1107/S1600536811027875

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2109

doi:10.1107/S1600536811027875

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4,6-Dimethyl-2-(naphthalen-1-yl)pyrimidine

Xiao-Xue Zhang,^a Deng-Yong Zhu,^a Xin-Qi Hao,^a Xin-Ming Dong ^a and Mao-Ping Song ^a ^*

^aDepartment of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: maopingsong@zzu.edu.cn

(Received 5 July 2011; accepted 12 July 2011; online 23 July 2011)

The asymmetric unit of the title compound, C₁₆H₁₄N₂, contains two independent molecules in which the dihedral angles between the pyrimidine and naphthaline rings are 38.20 (5) and 39.35 (5)°. Intermolecular C—H⋯π contacts and π–π stacking interactions [centroid–centroid distances = 3.766 (1) and 3.792 (1) Å] are present in the crystal structure.

Related literature

For cyclometalated Ir(III) complexes, see: Chen et al. (2010 ); Talarico et al. (2010 ); Xu et al. (2011 ); Yang et al. (2006 ). For the synthesis, see: Wang et al. (2011 ).

Experimental

Crystal data

C₁₆H₁₄N₂
M_r = 234.29
Monoclinic, P 2₁ /c
a = 14.9022 (18) Å
b = 11.4756 (14) Å
c = 15.9499 (19) Å
β = 111.028 (1)°
V = 2546.0 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.50 × 0.37 × 0.29 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.965, T_max = 0.979
18638 measured reflections
4733 independent reflections
3442 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.129
S = 1.06
4733 reflections
329 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg5 and Cg6 are the centroids of the N1/N2/C11–C14, C1/C2/C7–C10, N3/N4,C27–C30 and C17–C21/C26 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22⋯Cg1ⁱ	0.93	2.74	3.651 (4)	167
C13—H13⋯Cg2ⁱⁱ	0.93	2.76	3.597 (4)	150
C6—H6⋯Cg5	0.93	2.75	3.665 (2)	168
C29—H29⋯Cg6ⁱⁱⁱ	0.93	2.72	3.546 (3)	149
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811027875/si2364sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027875/si2364Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811027875/si2364Isup3.cml

checkCIF report

Comment top

In recent years, various types of cyclometalated Ir(III) complexes have been developed, such as homoleptic complexes, heteroleptic neutral complexes and cationic complexes (Chen et al., 2010; Talarico et al., 2010). In contrast to the most phenylpyridine ligands, few examples of naphthalenylpyrimidine iridium complexes have been reported (Xu et al., 2011; Yang et al., 2006). The title compound was obtained from the Suzuki coupling reaction with 1-naphthaleneboronic acid and 2-iodo-4,6-dimethylpyrimidine.

The crystal structure analysis of the title compound revealed that the asymmetric unit consists of two independent molecules (Fig. 1). The pyrimidine ring and naphthaline ring are not coplanar with the dihedral angles of 38.20 (5)° and 39.35 (5)°. All the bond distances and angles are within normal ranges. In the crystal of title compound there exist intermolecular C—H···π interactions (Table 1) and π—π stacking interactions [centroid-centroid distances Cg1 (N1,C11,N2,C12,C13,C14)···Cg7ⁱⁱ (C21–C26) and Cg3 (C2–C7)···Cg5ⁱⁱⁱ (N3,C27,N4,C28,C29,C30) are 3.7659 (12) and 3.7915 (12) Å, the perpendicular distances Cg1 on Cg7ⁱⁱ and Cg3 on Cg5ⁱⁱⁱ are 3.4761 (7) and 3.5318 (8) Å, respectively; [symmetry codes: ii = 1 - x, 1/2 + y, 1/2 - z; iii = - x, 1/2 + y, 1/2 - z] (see also Table 1). Cg2 and Cg6 are the centroids of the six-membered rings of the independent naphthyl units (C1,C2,C7,C8,C9,C10) and (C17 - C21,C26), respectively.

Related literature top

For cyclometalated Ir(III) complexes, see: Chen et al. (2010); Talarico et al. (2010); Xu et al. (2011); Yang et al. (2006). For the synthesis, see: Wang et al. (2011).

Experimental top

The title compound was obtained from the coupling reaction of 1-naphthaleneboronic acid and 2-iodo-4,6-dimethylpyrimidine as described in literature (Wang et al., 2011) and recrystallized from dichloromethane- petroleum ether solution at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 30% probability level.

4,6-Dimethyl-2-(naphthalen-1-yl)pyrimidine top

Crystal data top

C₁₆H₁₄N₂	F(000) = 992
M_r = 234.29	D_x = 1.222 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.9022 (18) Å	Cell parameters from 5588 reflections
b = 11.4756 (14) Å	θ = 2.4–27.4°
c = 15.9499 (19) Å	µ = 0.07 mm⁻¹
β = 111.028 (1)°	T = 296 K
V = 2546.0 (5) Å³	Block, colourless
Z = 8	0.50 × 0.37 × 0.29 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4733 independent reflections
Radiation source: fine-focus sealed tube	3442 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
T_min = 0.965, T_max = 0.979	k = −13→13
18638 measured reflections	l = −19→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0523P)² + 0.8594P] where P = (F_o² + 2F_c²)/3
4733 reflections	(Δ/σ)_max < 0.001
329 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₆H₁₄N₂	V = 2546.0 (5) Å³
M_r = 234.29	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.9022 (18) Å	µ = 0.07 mm⁻¹
b = 11.4756 (14) Å	T = 296 K
c = 15.9499 (19) Å	0.50 × 0.37 × 0.29 mm
β = 111.028 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4733 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3442 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.979	R_int = 0.023
18638 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.06	Δρ_max = 0.24 e Å⁻³
4733 reflections	Δρ_min = −0.18 e Å⁻³
329 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	0.33022 (12)	0.56804 (15)	0.19201 (11)	0.0391 (4)
C2	0.28518 (12)	0.54003 (15)	0.25537 (11)	0.0382 (4)
C3	0.31319 (13)	0.58798 (17)	0.34283 (12)	0.0466 (5)
H3	0.3632	0.6417	0.3614	0.056*
C4	0.26816 (14)	0.55681 (19)	0.40020 (13)	0.0545 (5)
H4	0.2882	0.5891	0.4575	0.065*
C5	0.19230 (15)	0.47692 (19)	0.37416 (14)	0.0574 (5)
H5	0.1631	0.4549	0.4144	0.069*
C6	0.16151 (14)	0.43166 (18)	0.29020 (14)	0.0535 (5)
H6	0.1102	0.3797	0.2729	0.064*
C7	0.20588 (12)	0.46173 (16)	0.22806 (12)	0.0429 (4)
C8	0.17279 (13)	0.41556 (17)	0.14022 (13)	0.0493 (5)
H8	0.1219	0.3630	0.1230	0.059*
C9	0.21425 (13)	0.44683 (17)	0.08061 (13)	0.0507 (5)
H9	0.1905	0.4175	0.0224	0.061*
C10	0.29303 (12)	0.52348 (16)	0.10659 (12)	0.0453 (4)
H10	0.3206	0.5445	0.0649	0.054*
C11	0.41918 (12)	0.63937 (15)	0.21483 (12)	0.0399 (4)
C12	0.50852 (13)	0.76663 (16)	0.16641 (13)	0.0466 (4)
C13	0.58104 (13)	0.75808 (17)	0.24906 (13)	0.0481 (5)
H13	0.6379	0.7995	0.2612	0.058*
C14	0.56827 (13)	0.68750 (16)	0.31349 (12)	0.0450 (4)
C15	0.51631 (16)	0.8421 (2)	0.09295 (15)	0.0643 (6)
H15A	0.4803	0.8079	0.0358	0.097*
H15B	0.5826	0.8489	0.0991	0.097*
H15C	0.4910	0.9180	0.0968	0.097*
C16	0.64365 (14)	0.67278 (19)	0.40496 (13)	0.0588 (5)
H16A	0.6343	0.7300	0.4450	0.088*
H16B	0.7061	0.6828	0.4014	0.088*
H16C	0.6388	0.5962	0.4271	0.088*
C17	0.12658 (11)	0.06318 (15)	0.19754 (11)	0.0357 (4)
C18	0.09762 (13)	0.01305 (17)	0.11404 (11)	0.0435 (4)
H18	0.0368	0.0304	0.0729	0.052*
C19	0.15642 (13)	−0.06341 (16)	0.08848 (12)	0.0454 (4)
H19	0.1345	−0.0962	0.0313	0.054*
C20	0.24584 (13)	−0.08964 (16)	0.14757 (12)	0.0440 (4)
H20	0.2842	−0.1420	0.1311	0.053*
C21	0.28081 (12)	−0.03786 (15)	0.23378 (11)	0.0381 (4)
C22	0.37491 (13)	−0.06205 (18)	0.29471 (13)	0.0501 (5)
H22	0.4136	−0.1140	0.2783	0.060*
C23	0.40930 (13)	−0.0107 (2)	0.37641 (13)	0.0561 (5)
H23	0.4709	−0.0283	0.4159	0.067*
C24	0.35244 (13)	0.06895 (18)	0.40169 (12)	0.0500 (5)
H24	0.3771	0.1048	0.4576	0.060*
C25	0.26154 (12)	0.09449 (16)	0.34545 (11)	0.0413 (4)
H25	0.2250	0.1479	0.3634	0.050*
C26	0.22168 (11)	0.04068 (14)	0.25978 (10)	0.0345 (4)
C27	0.05443 (11)	0.13401 (15)	0.21966 (11)	0.0360 (4)
C28	−0.01736 (12)	0.18418 (16)	0.31890 (12)	0.0425 (4)
C29	−0.08211 (12)	0.25082 (16)	0.25319 (12)	0.0432 (4)
H29	−0.1305	0.2911	0.2649	0.052*
C30	−0.07448 (12)	0.25720 (15)	0.16983 (12)	0.0407 (4)
C31	−0.02058 (15)	0.1730 (2)	0.41097 (13)	0.0608 (6)
H31A	0.0023	0.0973	0.4347	0.091*
H31B	−0.0855	0.1828	0.4082	0.091*
H31C	0.0195	0.2317	0.4493	0.091*
C32	−0.14053 (14)	0.33086 (18)	0.09602 (13)	0.0548 (5)
H32A	−0.1143	0.4079	0.0998	0.082*
H32B	−0.2023	0.3348	0.1019	0.082*
H32C	−0.1473	0.2971	0.0390	0.082*
N1	0.48627 (10)	0.62722 (13)	0.29660 (10)	0.0437 (4)
N2	0.42607 (10)	0.70672 (13)	0.14848 (10)	0.0443 (4)
N3	−0.00560 (10)	0.19787 (12)	0.15203 (9)	0.0395 (3)
N4	0.05243 (10)	0.12487 (13)	0.30227 (9)	0.0406 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0340 (9)	0.0402 (10)	0.0421 (10)	0.0027 (7)	0.0125 (7)	0.0004 (8)
C2	0.0324 (8)	0.0386 (10)	0.0423 (10)	0.0043 (7)	0.0119 (7)	0.0018 (7)
C3	0.0382 (9)	0.0543 (12)	0.0478 (11)	−0.0007 (8)	0.0160 (8)	−0.0062 (9)
C4	0.0525 (12)	0.0654 (13)	0.0480 (11)	0.0035 (10)	0.0212 (9)	−0.0036 (10)
C5	0.0562 (12)	0.0655 (14)	0.0593 (13)	−0.0010 (10)	0.0315 (10)	0.0055 (11)
C6	0.0465 (11)	0.0546 (12)	0.0631 (13)	−0.0071 (9)	0.0240 (10)	0.0014 (10)
C7	0.0358 (9)	0.0429 (10)	0.0493 (11)	0.0013 (8)	0.0145 (8)	0.0025 (8)
C8	0.0402 (10)	0.0505 (12)	0.0530 (11)	−0.0065 (8)	0.0118 (9)	−0.0033 (9)
C9	0.0485 (11)	0.0533 (12)	0.0447 (11)	−0.0035 (9)	0.0100 (9)	−0.0068 (9)
C10	0.0433 (10)	0.0496 (11)	0.0437 (10)	0.0003 (8)	0.0165 (8)	0.0014 (8)
C11	0.0382 (9)	0.0386 (10)	0.0453 (10)	0.0041 (7)	0.0178 (8)	−0.0016 (8)
C12	0.0456 (10)	0.0429 (11)	0.0573 (12)	0.0013 (8)	0.0257 (9)	−0.0002 (9)
C13	0.0406 (10)	0.0461 (11)	0.0606 (12)	−0.0068 (8)	0.0220 (9)	−0.0064 (9)
C14	0.0396 (9)	0.0449 (11)	0.0516 (11)	0.0005 (8)	0.0179 (8)	−0.0064 (9)
C15	0.0676 (14)	0.0621 (14)	0.0678 (14)	−0.0064 (11)	0.0298 (11)	0.0121 (11)
C16	0.0483 (11)	0.0662 (14)	0.0560 (12)	−0.0050 (10)	0.0115 (9)	−0.0046 (10)
C17	0.0349 (9)	0.0390 (9)	0.0348 (9)	0.0030 (7)	0.0143 (7)	0.0021 (7)
C18	0.0406 (9)	0.0518 (11)	0.0356 (9)	0.0068 (8)	0.0108 (8)	−0.0008 (8)
C19	0.0510 (11)	0.0490 (11)	0.0377 (10)	0.0040 (9)	0.0179 (8)	−0.0056 (8)
C20	0.0470 (10)	0.0450 (11)	0.0468 (10)	0.0067 (8)	0.0251 (8)	−0.0020 (8)
C21	0.0360 (9)	0.0390 (10)	0.0433 (10)	0.0033 (7)	0.0190 (8)	0.0053 (7)
C22	0.0404 (10)	0.0549 (12)	0.0557 (12)	0.0135 (9)	0.0182 (9)	0.0046 (9)
C23	0.0373 (10)	0.0699 (14)	0.0528 (12)	0.0095 (10)	0.0061 (9)	0.0055 (10)
C24	0.0425 (10)	0.0611 (13)	0.0412 (10)	−0.0032 (9)	0.0086 (8)	−0.0025 (9)
C25	0.0380 (9)	0.0453 (10)	0.0418 (10)	0.0000 (8)	0.0159 (8)	−0.0017 (8)
C26	0.0340 (8)	0.0365 (9)	0.0366 (9)	0.0012 (7)	0.0169 (7)	0.0035 (7)
C27	0.0333 (8)	0.0366 (9)	0.0375 (9)	0.0001 (7)	0.0121 (7)	−0.0011 (7)
C28	0.0379 (9)	0.0501 (11)	0.0412 (10)	0.0036 (8)	0.0163 (8)	−0.0003 (8)
C29	0.0380 (9)	0.0469 (11)	0.0458 (10)	0.0099 (8)	0.0165 (8)	−0.0017 (8)
C30	0.0381 (9)	0.0391 (10)	0.0435 (10)	0.0044 (8)	0.0129 (8)	−0.0002 (8)
C31	0.0629 (13)	0.0800 (16)	0.0458 (11)	0.0202 (11)	0.0271 (10)	0.0076 (10)
C32	0.0602 (12)	0.0546 (12)	0.0471 (11)	0.0209 (10)	0.0162 (9)	0.0075 (9)
N1	0.0383 (8)	0.0447 (9)	0.0482 (9)	−0.0011 (7)	0.0158 (7)	−0.0022 (7)
N2	0.0426 (8)	0.0431 (9)	0.0499 (9)	0.0018 (7)	0.0200 (7)	0.0003 (7)
N3	0.0381 (8)	0.0402 (8)	0.0399 (8)	0.0045 (6)	0.0136 (6)	0.0015 (6)
N4	0.0377 (8)	0.0465 (9)	0.0392 (8)	0.0066 (7)	0.0159 (6)	0.0019 (7)

Geometric parameters (Å, º) top

C1—C10	1.372 (2)	C17—C18	1.371 (2)
C1—C2	1.436 (2)	C17—C26	1.432 (2)
C1—C11	1.488 (2)	C17—C27	1.488 (2)
C2—C3	1.416 (2)	C18—C19	1.400 (2)
C2—C7	1.423 (2)	C18—H18	0.9300
C3—C4	1.362 (3)	C19—C20	1.361 (2)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.398 (3)	C20—C21	1.415 (2)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.354 (3)	C21—C22	1.418 (2)
C5—H5	0.9300	C21—C26	1.422 (2)
C6—C7	1.417 (3)	C22—C23	1.353 (3)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.411 (3)	C23—C24	1.400 (3)
C8—C9	1.355 (3)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.361 (2)
C9—C10	1.405 (3)	C24—H24	0.9300
C9—H9	0.9300	C25—C26	1.421 (2)
C10—H10	0.9300	C25—H25	0.9300
C11—N1	1.336 (2)	C27—N4	1.333 (2)
C11—N2	1.344 (2)	C27—N3	1.345 (2)
C12—N2	1.346 (2)	C28—N4	1.347 (2)
C12—C13	1.376 (3)	C28—C29	1.374 (2)
C12—C15	1.495 (3)	C28—C31	1.492 (2)
C13—C14	1.374 (3)	C29—C30	1.376 (2)
C13—H13	0.9300	C29—H29	0.9300
C14—N1	1.345 (2)	C30—N3	1.344 (2)
C14—C16	1.498 (3)	C30—C32	1.496 (2)
C15—H15A	0.9600	C31—H31A	0.9600
C15—H15B	0.9600	C31—H31B	0.9600
C15—H15C	0.9600	C31—H31C	0.9600
C16—H16A	0.9600	C32—H32A	0.9600
C16—H16B	0.9600	C32—H32B	0.9600
C16—H16C	0.9600	C32—H32C	0.9600

C10—C1—C2	119.41 (16)	C26—C17—C27	123.63 (14)
C10—C1—C11	117.06 (15)	C17—C18—C19	122.29 (16)
C2—C1—C11	123.47 (15)	C17—C18—H18	118.9
C3—C2—C7	117.77 (16)	C19—C18—H18	118.9
C3—C2—C1	124.01 (16)	C20—C19—C18	119.77 (16)
C7—C2—C1	118.20 (16)	C20—C19—H19	120.1
C4—C3—C2	121.16 (18)	C18—C19—H19	120.1
C4—C3—H3	119.4	C19—C20—C21	120.51 (16)
C2—C3—H3	119.4	C19—C20—H20	119.7
C3—C4—C5	120.89 (19)	C21—C20—H20	119.7
C3—C4—H4	119.6	C20—C21—C22	120.85 (16)
C5—C4—H4	119.6	C20—C21—C26	119.93 (15)
C6—C5—C4	119.76 (18)	C22—C21—C26	119.22 (16)
C6—C5—H5	120.1	C23—C22—C21	120.97 (17)
C4—C5—H5	120.1	C23—C22—H22	119.5
C5—C6—C7	121.38 (19)	C21—C22—H22	119.5
C5—C6—H6	119.3	C22—C23—C24	120.18 (17)
C7—C6—H6	119.3	C22—C23—H23	119.9
C8—C7—C6	121.22 (17)	C24—C23—H23	119.9
C8—C7—C2	119.81 (16)	C25—C24—C23	120.84 (18)
C6—C7—C2	118.97 (17)	C25—C24—H24	119.6
C9—C8—C7	120.82 (17)	C23—C24—H24	119.6
C9—C8—H8	119.6	C24—C25—C26	120.92 (17)
C7—C8—H8	119.6	C24—C25—H25	119.5
C8—C9—C10	120.13 (18)	C26—C25—H25	119.5
C8—C9—H9	119.9	C25—C26—C21	117.83 (15)
C10—C9—H9	119.9	C25—C26—C17	123.81 (15)
C1—C10—C9	121.54 (17)	C21—C26—C17	118.34 (15)
C1—C10—H10	119.2	N4—C27—N3	126.26 (15)
C9—C10—H10	119.2	N4—C27—C17	117.76 (14)
N1—C11—N2	125.94 (16)	N3—C27—C17	115.91 (14)
N1—C11—C1	118.07 (15)	N4—C28—C29	120.77 (16)
N2—C11—C1	115.91 (15)	N4—C28—C31	116.77 (16)
N2—C12—C13	120.69 (17)	C29—C28—C31	122.47 (16)
N2—C12—C15	116.82 (17)	C28—C29—C30	119.18 (16)
C13—C12—C15	122.50 (18)	C28—C29—H29	120.4
C14—C13—C12	119.12 (17)	C30—C29—H29	120.4
C14—C13—H13	120.4	N3—C30—C29	120.73 (16)
C12—C13—H13	120.4	N3—C30—C32	117.18 (16)
N1—C14—C13	120.87 (17)	C29—C30—C32	122.09 (16)
N1—C14—C16	116.57 (17)	C28—C31—H31A	109.5
C13—C14—C16	122.56 (17)	C28—C31—H31B	109.5
C12—C15—H15A	109.5	H31A—C31—H31B	109.5
C12—C15—H15B	109.5	C28—C31—H31C	109.5
H15A—C15—H15B	109.5	H31A—C31—H31C	109.5
C12—C15—H15C	109.5	H31B—C31—H31C	109.5
H15A—C15—H15C	109.5	C30—C32—H32A	109.5
H15B—C15—H15C	109.5	C30—C32—H32B	109.5
C14—C16—H16A	109.5	H32A—C32—H32B	109.5
C14—C16—H16B	109.5	C30—C32—H32C	109.5
H16A—C16—H16B	109.5	H32A—C32—H32C	109.5
C14—C16—H16C	109.5	H32B—C32—H32C	109.5
H16A—C16—H16C	109.5	C11—N1—C14	116.74 (15)
H16B—C16—H16C	109.5	C11—N2—C12	116.63 (15)
C18—C17—C26	119.09 (15)	C30—N3—C27	116.44 (14)
C18—C17—C27	117.21 (14)	C27—N4—C28	116.61 (14)

C10—C1—C2—C3	−175.15 (17)	C21—C22—C23—C24	−0.8 (3)
C11—C1—C2—C3	7.8 (3)	C22—C23—C24—C25	1.1 (3)
C10—C1—C2—C7	3.1 (2)	C23—C24—C25—C26	0.3 (3)
C11—C1—C2—C7	−173.91 (16)	C24—C25—C26—C21	−1.9 (3)
C7—C2—C3—C4	2.5 (3)	C24—C25—C26—C17	179.75 (17)
C1—C2—C3—C4	−179.26 (18)	C20—C21—C26—C25	−177.21 (15)
C2—C3—C4—C5	−0.4 (3)	C22—C21—C26—C25	2.0 (2)
C3—C4—C5—C6	−1.5 (3)	C20—C21—C26—C17	1.3 (2)
C4—C5—C6—C7	1.3 (3)	C22—C21—C26—C17	−179.48 (15)
C5—C6—C7—C8	−179.16 (19)	C18—C17—C26—C25	175.28 (16)
C5—C6—C7—C2	0.8 (3)	C27—C17—C26—C25	−7.9 (3)
C3—C2—C7—C8	177.34 (16)	C18—C17—C26—C21	−3.1 (2)
C1—C2—C7—C8	−1.0 (3)	C27—C17—C26—C21	173.76 (15)
C3—C2—C7—C6	−2.6 (3)	C18—C17—C27—N4	140.10 (17)
C1—C2—C7—C6	179.01 (16)	C26—C17—C27—N4	−36.8 (2)
C6—C7—C8—C9	178.50 (19)	C18—C17—C27—N3	−37.2 (2)
C2—C7—C8—C9	−1.5 (3)	C26—C17—C27—N3	145.92 (16)
C7—C8—C9—C10	1.9 (3)	N4—C28—C29—C30	−0.5 (3)
C2—C1—C10—C9	−2.8 (3)	C31—C28—C29—C30	179.84 (19)
C11—C1—C10—C9	174.40 (16)	C28—C29—C30—N3	1.0 (3)
C8—C9—C10—C1	0.3 (3)	C28—C29—C30—C32	−178.10 (17)
C10—C1—C11—N1	−140.99 (17)	N2—C11—N1—C14	−0.5 (3)
C2—C1—C11—N1	36.1 (2)	C1—C11—N1—C14	176.14 (15)
C10—C1—C11—N2	35.9 (2)	C13—C14—N1—C11	0.2 (2)
C2—C1—C11—N2	−146.97 (16)	C16—C14—N1—C11	−179.46 (16)
N2—C12—C13—C14	−0.1 (3)	N1—C11—N2—C12	0.4 (3)
C15—C12—C13—C14	179.50 (18)	C1—C11—N2—C12	−176.27 (15)
C12—C13—C14—N1	0.0 (3)	C13—C12—N2—C11	−0.1 (2)
C12—C13—C14—C16	179.70 (18)	C15—C12—N2—C11	−179.72 (17)
C26—C17—C18—C19	2.7 (3)	C29—C30—N3—C27	−0.5 (2)
C27—C17—C18—C19	−174.41 (17)	C32—C30—N3—C27	178.65 (16)
C17—C18—C19—C20	−0.2 (3)	N4—C27—N3—C30	−0.6 (3)
C18—C19—C20—C21	−1.7 (3)	C17—C27—N3—C30	176.45 (15)
C19—C20—C21—C22	−178.11 (18)	N3—C27—N4—C28	1.0 (3)
C19—C20—C21—C26	1.1 (3)	C17—C27—N4—C28	−175.97 (15)
C20—C21—C22—C23	178.51 (18)	C29—C28—N4—C27	−0.4 (3)
C26—C21—C22—C23	−0.7 (3)	C31—C28—N4—C27	179.27 (17)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg5 and Cg6 are the centroids of the N1/N2/C11–C14, C1/C2/C7–C10, N3/N4,C27–C30 and C17–C21/C26 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···Cg1ⁱ	0.93	2.74	3.651 (4)	167
C13—H13···Cg2ⁱⁱ	0.93	2.76	3.597 (4)	150
C6—H6···Cg5	0.93	2.75	3.665 (2)	168
C29—H29···Cg6ⁱⁱⁱ	0.93	2.72	3.546 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂
M_r	234.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	14.9022 (18), 11.4756 (14), 15.9499 (19)
β (°)	111.028 (1)
V (Å³)	2546.0 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.50 × 0.37 × 0.29

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.965, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	18638, 4733, 3442
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.129, 1.06
No. of reflections	4733
No. of parameters	329
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.18

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg5 and Cg6 are the centroids of the N1/N2/C11–C14, C1/C2/C7–C10, N3/N4,C27–C30 and C17–C21/C26 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···Cg1ⁱ	0.93	2.74	3.651 (4)	167
C13—H13···Cg2ⁱⁱ	0.93	2.76	3.597 (4)	150
C6—H6···Cg5	0.93	2.75	3.665 (2)	168
C29—H29···Cg6ⁱⁱⁱ	0.93	2.72	3.546 (3)	149

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

Acknowledgements

This work was sponsored by the National Natural Science Foundation of China (No. 20872133) and the Natural Science Foundation of Henan Education Department (No. 2009 A150027).

References

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