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ISSN: 2056-9890

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

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 ππ 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[Chen, Z. Q., Bian, Z. Q. & Huang, C. H. (2010). Adv. Mater. 22, 1534-1539.]); Talarico et al. (2010[Talarico, A. M., Aiello, I., Bellusci, A., Crispini, A., Ghedini, M., Godbert, N., Pugliese, T. & Szerb, E. (2010). Dalton Trans. 39, 1709-1712.]); Xu et al. (2011[Xu, C., Wang, Z. Q., Dong, X. M., Hao, X. Q., Zhao, X. M., Ji, B. M. & Song, M. P. (2011). Inorg. Chim. Acta, 373, 306-310.]); Yang et al. (2006[Yang, C. H., Chen, C. H. & Sun, I. W. (2006). Polyhedron, 25, 2407-2414.]). For the synthesis, see: Wang et al. (2011[Wang, Z. Q., Xu, C., Dong, X. M., Zhang, Y. P., Hao, X. Q., Gong, J. F., Song, M. P. & Ji, B. M. (2011). Inorg. Chem. Commun. 14, 316-319.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14N2

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.965, Tmax = 0.979

  • 18638 measured reflections

  • 4733 independent reflections

  • 3442 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.129

  • S = 1.06

  • 4733 reflections

  • 329 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −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 DA 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[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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 ππ 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.

Refinement top

H atoms attached to C atoms of the title compound were placed in geometrically idealized positions and treated as riding with C—H distances constrained to 0.93–0.96 Å, and with Uiso(H)=1.2.Ueq(C), 1.5.U eq(methyl H).

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
[Figure 1] 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
C16H14N2F(000) = 992
Mr = 234.29Dx = 1.222 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.9022 (18) ÅCell parameters from 5588 reflections
b = 11.4756 (14) Åθ = 2.4–27.4°
c = 15.9499 (19) ŵ = 0.07 mm1
β = 111.028 (1)°T = 296 K
V = 2546.0 (5) Å3Block, colourless
Z = 80.50 × 0.37 × 0.29 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4733 independent reflections
Radiation source: fine-focus sealed tube3442 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ϕ and ω scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1818
Tmin = 0.965, Tmax = 0.979k = 1313
18638 measured reflectionsl = 1919
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0523P)2 + 0.8594P]
where P = (Fo2 + 2Fc2)/3
4733 reflections(Δ/σ)max < 0.001
329 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C16H14N2V = 2546.0 (5) Å3
Mr = 234.29Z = 8
Monoclinic, P21/cMo Kα radiation
a = 14.9022 (18) ŵ = 0.07 mm1
b = 11.4756 (14) ÅT = 296 K
c = 15.9499 (19) Å0.50 × 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)
Tmin = 0.965, Tmax = 0.979Rint = 0.023
18638 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.129H-atom parameters constrained
S = 1.06Δρmax = 0.24 e Å3
4733 reflectionsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
C10.33022 (12)0.56804 (15)0.19201 (11)0.0391 (4)
C20.28518 (12)0.54003 (15)0.25537 (11)0.0382 (4)
C30.31319 (13)0.58798 (17)0.34283 (12)0.0466 (5)
H30.36320.64170.36140.056*
C40.26816 (14)0.55681 (19)0.40020 (13)0.0545 (5)
H40.28820.58910.45750.065*
C50.19230 (15)0.47692 (19)0.37416 (14)0.0574 (5)
H50.16310.45490.41440.069*
C60.16151 (14)0.43166 (18)0.29020 (14)0.0535 (5)
H60.11020.37970.27290.064*
C70.20588 (12)0.46173 (16)0.22806 (12)0.0429 (4)
C80.17279 (13)0.41556 (17)0.14022 (13)0.0493 (5)
H80.12190.36300.12300.059*
C90.21425 (13)0.44683 (17)0.08061 (13)0.0507 (5)
H90.19050.41750.02240.061*
C100.29303 (12)0.52348 (16)0.10659 (12)0.0453 (4)
H100.32060.54450.06490.054*
C110.41918 (12)0.63937 (15)0.21483 (12)0.0399 (4)
C120.50852 (13)0.76663 (16)0.16641 (13)0.0466 (4)
C130.58104 (13)0.75808 (17)0.24906 (13)0.0481 (5)
H130.63790.79950.26120.058*
C140.56827 (13)0.68750 (16)0.31349 (12)0.0450 (4)
C150.51631 (16)0.8421 (2)0.09295 (15)0.0643 (6)
H15A0.48030.80790.03580.097*
H15B0.58260.84890.09910.097*
H15C0.49100.91800.09680.097*
C160.64365 (14)0.67278 (19)0.40496 (13)0.0588 (5)
H16A0.63430.73000.44500.088*
H16B0.70610.68280.40140.088*
H16C0.63880.59620.42710.088*
C170.12658 (11)0.06318 (15)0.19754 (11)0.0357 (4)
C180.09762 (13)0.01305 (17)0.11404 (11)0.0435 (4)
H180.03680.03040.07290.052*
C190.15642 (13)0.06341 (16)0.08848 (12)0.0454 (4)
H190.13450.09620.03130.054*
C200.24584 (13)0.08964 (16)0.14757 (12)0.0440 (4)
H200.28420.14200.13110.053*
C210.28081 (12)0.03786 (15)0.23378 (11)0.0381 (4)
C220.37491 (13)0.06205 (18)0.29471 (13)0.0501 (5)
H220.41360.11400.27830.060*
C230.40930 (13)0.0107 (2)0.37641 (13)0.0561 (5)
H230.47090.02830.41590.067*
C240.35244 (13)0.06895 (18)0.40169 (12)0.0500 (5)
H240.37710.10480.45760.060*
C250.26154 (12)0.09449 (16)0.34545 (11)0.0413 (4)
H250.22500.14790.36340.050*
C260.22168 (11)0.04068 (14)0.25978 (10)0.0345 (4)
C270.05443 (11)0.13401 (15)0.21966 (11)0.0360 (4)
C280.01736 (12)0.18418 (16)0.31890 (12)0.0425 (4)
C290.08211 (12)0.25082 (16)0.25319 (12)0.0432 (4)
H290.13050.29110.26490.052*
C300.07448 (12)0.25720 (15)0.16983 (12)0.0407 (4)
C310.02058 (15)0.1730 (2)0.41097 (13)0.0608 (6)
H31A0.00230.09730.43470.091*
H31B0.08550.18280.40820.091*
H31C0.01950.23170.44930.091*
C320.14053 (14)0.33086 (18)0.09602 (13)0.0548 (5)
H32A0.11430.40790.09980.082*
H32B0.20230.33480.10190.082*
H32C0.14730.29710.03900.082*
N10.48627 (10)0.62722 (13)0.29660 (10)0.0437 (4)
N20.42607 (10)0.70672 (13)0.14848 (10)0.0443 (4)
N30.00560 (10)0.19787 (12)0.15203 (9)0.0395 (3)
N40.05243 (10)0.12487 (13)0.30227 (9)0.0406 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0340 (9)0.0402 (10)0.0421 (10)0.0027 (7)0.0125 (7)0.0004 (8)
C20.0324 (8)0.0386 (10)0.0423 (10)0.0043 (7)0.0119 (7)0.0018 (7)
C30.0382 (9)0.0543 (12)0.0478 (11)0.0007 (8)0.0160 (8)0.0062 (9)
C40.0525 (12)0.0654 (13)0.0480 (11)0.0035 (10)0.0212 (9)0.0036 (10)
C50.0562 (12)0.0655 (14)0.0593 (13)0.0010 (10)0.0315 (10)0.0055 (11)
C60.0465 (11)0.0546 (12)0.0631 (13)0.0071 (9)0.0240 (10)0.0014 (10)
C70.0358 (9)0.0429 (10)0.0493 (11)0.0013 (8)0.0145 (8)0.0025 (8)
C80.0402 (10)0.0505 (12)0.0530 (11)0.0065 (8)0.0118 (9)0.0033 (9)
C90.0485 (11)0.0533 (12)0.0447 (11)0.0035 (9)0.0100 (9)0.0068 (9)
C100.0433 (10)0.0496 (11)0.0437 (10)0.0003 (8)0.0165 (8)0.0014 (8)
C110.0382 (9)0.0386 (10)0.0453 (10)0.0041 (7)0.0178 (8)0.0016 (8)
C120.0456 (10)0.0429 (11)0.0573 (12)0.0013 (8)0.0257 (9)0.0002 (9)
C130.0406 (10)0.0461 (11)0.0606 (12)0.0068 (8)0.0220 (9)0.0064 (9)
C140.0396 (9)0.0449 (11)0.0516 (11)0.0005 (8)0.0179 (8)0.0064 (9)
C150.0676 (14)0.0621 (14)0.0678 (14)0.0064 (11)0.0298 (11)0.0121 (11)
C160.0483 (11)0.0662 (14)0.0560 (12)0.0050 (10)0.0115 (9)0.0046 (10)
C170.0349 (9)0.0390 (9)0.0348 (9)0.0030 (7)0.0143 (7)0.0021 (7)
C180.0406 (9)0.0518 (11)0.0356 (9)0.0068 (8)0.0108 (8)0.0008 (8)
C190.0510 (11)0.0490 (11)0.0377 (10)0.0040 (9)0.0179 (8)0.0056 (8)
C200.0470 (10)0.0450 (11)0.0468 (10)0.0067 (8)0.0251 (8)0.0020 (8)
C210.0360 (9)0.0390 (10)0.0433 (10)0.0033 (7)0.0190 (8)0.0053 (7)
C220.0404 (10)0.0549 (12)0.0557 (12)0.0135 (9)0.0182 (9)0.0046 (9)
C230.0373 (10)0.0699 (14)0.0528 (12)0.0095 (10)0.0061 (9)0.0055 (10)
C240.0425 (10)0.0611 (13)0.0412 (10)0.0032 (9)0.0086 (8)0.0025 (9)
C250.0380 (9)0.0453 (10)0.0418 (10)0.0000 (8)0.0159 (8)0.0017 (8)
C260.0340 (8)0.0365 (9)0.0366 (9)0.0012 (7)0.0169 (7)0.0035 (7)
C270.0333 (8)0.0366 (9)0.0375 (9)0.0001 (7)0.0121 (7)0.0011 (7)
C280.0379 (9)0.0501 (11)0.0412 (10)0.0036 (8)0.0163 (8)0.0003 (8)
C290.0380 (9)0.0469 (11)0.0458 (10)0.0099 (8)0.0165 (8)0.0017 (8)
C300.0381 (9)0.0391 (10)0.0435 (10)0.0044 (8)0.0129 (8)0.0002 (8)
C310.0629 (13)0.0800 (16)0.0458 (11)0.0202 (11)0.0271 (10)0.0076 (10)
C320.0602 (12)0.0546 (12)0.0471 (11)0.0209 (10)0.0162 (9)0.0075 (9)
N10.0383 (8)0.0447 (9)0.0482 (9)0.0011 (7)0.0158 (7)0.0022 (7)
N20.0426 (8)0.0431 (9)0.0499 (9)0.0018 (7)0.0200 (7)0.0003 (7)
N30.0381 (8)0.0402 (8)0.0399 (8)0.0045 (6)0.0136 (6)0.0015 (6)
N40.0377 (8)0.0465 (9)0.0392 (8)0.0066 (7)0.0159 (6)0.0019 (7)
Geometric parameters (Å, º) top
C1—C101.372 (2)C17—C181.371 (2)
C1—C21.436 (2)C17—C261.432 (2)
C1—C111.488 (2)C17—C271.488 (2)
C2—C31.416 (2)C18—C191.400 (2)
C2—C71.423 (2)C18—H180.9300
C3—C41.362 (3)C19—C201.361 (2)
C3—H30.9300C19—H190.9300
C4—C51.398 (3)C20—C211.415 (2)
C4—H40.9300C20—H200.9300
C5—C61.354 (3)C21—C221.418 (2)
C5—H50.9300C21—C261.422 (2)
C6—C71.417 (3)C22—C231.353 (3)
C6—H60.9300C22—H220.9300
C7—C81.411 (3)C23—C241.400 (3)
C8—C91.355 (3)C23—H230.9300
C8—H80.9300C24—C251.361 (2)
C9—C101.405 (3)C24—H240.9300
C9—H90.9300C25—C261.421 (2)
C10—H100.9300C25—H250.9300
C11—N11.336 (2)C27—N41.333 (2)
C11—N21.344 (2)C27—N31.345 (2)
C12—N21.346 (2)C28—N41.347 (2)
C12—C131.376 (3)C28—C291.374 (2)
C12—C151.495 (3)C28—C311.492 (2)
C13—C141.374 (3)C29—C301.376 (2)
C13—H130.9300C29—H290.9300
C14—N11.345 (2)C30—N31.344 (2)
C14—C161.498 (3)C30—C321.496 (2)
C15—H15A0.9600C31—H31A0.9600
C15—H15B0.9600C31—H31B0.9600
C15—H15C0.9600C31—H31C0.9600
C16—H16A0.9600C32—H32A0.9600
C16—H16B0.9600C32—H32B0.9600
C16—H16C0.9600C32—H32C0.9600
C10—C1—C2119.41 (16)C26—C17—C27123.63 (14)
C10—C1—C11117.06 (15)C17—C18—C19122.29 (16)
C2—C1—C11123.47 (15)C17—C18—H18118.9
C3—C2—C7117.77 (16)C19—C18—H18118.9
C3—C2—C1124.01 (16)C20—C19—C18119.77 (16)
C7—C2—C1118.20 (16)C20—C19—H19120.1
C4—C3—C2121.16 (18)C18—C19—H19120.1
C4—C3—H3119.4C19—C20—C21120.51 (16)
C2—C3—H3119.4C19—C20—H20119.7
C3—C4—C5120.89 (19)C21—C20—H20119.7
C3—C4—H4119.6C20—C21—C22120.85 (16)
C5—C4—H4119.6C20—C21—C26119.93 (15)
C6—C5—C4119.76 (18)C22—C21—C26119.22 (16)
C6—C5—H5120.1C23—C22—C21120.97 (17)
C4—C5—H5120.1C23—C22—H22119.5
C5—C6—C7121.38 (19)C21—C22—H22119.5
C5—C6—H6119.3C22—C23—C24120.18 (17)
C7—C6—H6119.3C22—C23—H23119.9
C8—C7—C6121.22 (17)C24—C23—H23119.9
C8—C7—C2119.81 (16)C25—C24—C23120.84 (18)
C6—C7—C2118.97 (17)C25—C24—H24119.6
C9—C8—C7120.82 (17)C23—C24—H24119.6
C9—C8—H8119.6C24—C25—C26120.92 (17)
C7—C8—H8119.6C24—C25—H25119.5
C8—C9—C10120.13 (18)C26—C25—H25119.5
C8—C9—H9119.9C25—C26—C21117.83 (15)
C10—C9—H9119.9C25—C26—C17123.81 (15)
C1—C10—C9121.54 (17)C21—C26—C17118.34 (15)
C1—C10—H10119.2N4—C27—N3126.26 (15)
C9—C10—H10119.2N4—C27—C17117.76 (14)
N1—C11—N2125.94 (16)N3—C27—C17115.91 (14)
N1—C11—C1118.07 (15)N4—C28—C29120.77 (16)
N2—C11—C1115.91 (15)N4—C28—C31116.77 (16)
N2—C12—C13120.69 (17)C29—C28—C31122.47 (16)
N2—C12—C15116.82 (17)C28—C29—C30119.18 (16)
C13—C12—C15122.50 (18)C28—C29—H29120.4
C14—C13—C12119.12 (17)C30—C29—H29120.4
C14—C13—H13120.4N3—C30—C29120.73 (16)
C12—C13—H13120.4N3—C30—C32117.18 (16)
N1—C14—C13120.87 (17)C29—C30—C32122.09 (16)
N1—C14—C16116.57 (17)C28—C31—H31A109.5
C13—C14—C16122.56 (17)C28—C31—H31B109.5
C12—C15—H15A109.5H31A—C31—H31B109.5
C12—C15—H15B109.5C28—C31—H31C109.5
H15A—C15—H15B109.5H31A—C31—H31C109.5
C12—C15—H15C109.5H31B—C31—H31C109.5
H15A—C15—H15C109.5C30—C32—H32A109.5
H15B—C15—H15C109.5C30—C32—H32B109.5
C14—C16—H16A109.5H32A—C32—H32B109.5
C14—C16—H16B109.5C30—C32—H32C109.5
H16A—C16—H16B109.5H32A—C32—H32C109.5
C14—C16—H16C109.5H32B—C32—H32C109.5
H16A—C16—H16C109.5C11—N1—C14116.74 (15)
H16B—C16—H16C109.5C11—N2—C12116.63 (15)
C18—C17—C26119.09 (15)C30—N3—C27116.44 (14)
C18—C17—C27117.21 (14)C27—N4—C28116.61 (14)
C10—C1—C2—C3175.15 (17)C21—C22—C23—C240.8 (3)
C11—C1—C2—C37.8 (3)C22—C23—C24—C251.1 (3)
C10—C1—C2—C73.1 (2)C23—C24—C25—C260.3 (3)
C11—C1—C2—C7173.91 (16)C24—C25—C26—C211.9 (3)
C7—C2—C3—C42.5 (3)C24—C25—C26—C17179.75 (17)
C1—C2—C3—C4179.26 (18)C20—C21—C26—C25177.21 (15)
C2—C3—C4—C50.4 (3)C22—C21—C26—C252.0 (2)
C3—C4—C5—C61.5 (3)C20—C21—C26—C171.3 (2)
C4—C5—C6—C71.3 (3)C22—C21—C26—C17179.48 (15)
C5—C6—C7—C8179.16 (19)C18—C17—C26—C25175.28 (16)
C5—C6—C7—C20.8 (3)C27—C17—C26—C257.9 (3)
C3—C2—C7—C8177.34 (16)C18—C17—C26—C213.1 (2)
C1—C2—C7—C81.0 (3)C27—C17—C26—C21173.76 (15)
C3—C2—C7—C62.6 (3)C18—C17—C27—N4140.10 (17)
C1—C2—C7—C6179.01 (16)C26—C17—C27—N436.8 (2)
C6—C7—C8—C9178.50 (19)C18—C17—C27—N337.2 (2)
C2—C7—C8—C91.5 (3)C26—C17—C27—N3145.92 (16)
C7—C8—C9—C101.9 (3)N4—C28—C29—C300.5 (3)
C2—C1—C10—C92.8 (3)C31—C28—C29—C30179.84 (19)
C11—C1—C10—C9174.40 (16)C28—C29—C30—N31.0 (3)
C8—C9—C10—C10.3 (3)C28—C29—C30—C32178.10 (17)
C10—C1—C11—N1140.99 (17)N2—C11—N1—C140.5 (3)
C2—C1—C11—N136.1 (2)C1—C11—N1—C14176.14 (15)
C10—C1—C11—N235.9 (2)C13—C14—N1—C110.2 (2)
C2—C1—C11—N2146.97 (16)C16—C14—N1—C11179.46 (16)
N2—C12—C13—C140.1 (3)N1—C11—N2—C120.4 (3)
C15—C12—C13—C14179.50 (18)C1—C11—N2—C12176.27 (15)
C12—C13—C14—N10.0 (3)C13—C12—N2—C110.1 (2)
C12—C13—C14—C16179.70 (18)C15—C12—N2—C11179.72 (17)
C26—C17—C18—C192.7 (3)C29—C30—N3—C270.5 (2)
C27—C17—C18—C19174.41 (17)C32—C30—N3—C27178.65 (16)
C17—C18—C19—C200.2 (3)N4—C27—N3—C300.6 (3)
C18—C19—C20—C211.7 (3)C17—C27—N3—C30176.45 (15)
C19—C20—C21—C22178.11 (18)N3—C27—N4—C281.0 (3)
C19—C20—C21—C261.1 (3)C17—C27—N4—C28175.97 (15)
C20—C21—C22—C23178.51 (18)C29—C28—N4—C270.4 (3)
C26—C21—C22—C230.7 (3)C31—C28—N4—C27179.27 (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···AD—HH···AD···AD—H···A
C22—H22···Cg1i0.932.743.651 (4)167
C13—H13···Cg2ii0.932.763.597 (4)150
C6—H6···Cg50.932.753.665 (2)168
C29—H29···Cg6iii0.932.723.546 (3)149
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC16H14N2
Mr234.29
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)14.9022 (18), 11.4756 (14), 15.9499 (19)
β (°) 111.028 (1)
V3)2546.0 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.50 × 0.37 × 0.29
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.965, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
18638, 4733, 3442
Rint0.023
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.129, 1.06
No. of reflections4733
No. of parameters329
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C22—H22···Cg1i0.932.743.651 (4)167
C13—H13···Cg2ii0.932.763.597 (4)150
C6—H6···Cg50.932.753.665 (2)168
C29—H29···Cg6iii0.932.723.546 (3)149
Symmetry codes: (i) x, y1, 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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First citationXu, C., Wang, Z. Q., Dong, X. M., Hao, X. Q., Zhao, X. M., Ji, B. M. & Song, M. P. (2011). Inorg. Chim. Acta, 373, 306–310.  Web of Science CSD CrossRef CAS Google Scholar
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