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ISSN: 2056-9890

1,2,4,5-Tetra­phenyl-1H-imidazole

aChemistry and Chemical Engineering Institute, Qiqihar University, Heilongjiang Qiqihar 161006, People's Republic of China
*Correspondence e-mail: zhao_submit@yahoo.com.cn

(Received 16 January 2012; accepted 25 January 2012; online 31 January 2012)

The asymmetric unit of the title compound, C27H20N2, contains two independent mol­ecules, A and B. In both mol­ecules, the N atom in the 1-position and the C atom in the 5-position are statistically disordered [as 0.571 (8):0.429 (8) in A and 0.736 (9):0.264 (9) in B]. The phenyl rings in the 1-, 2-, 4- and 5-positions in A are twisted from the central imidazole ring by 84.3 (2), 21.6 (2), 21.5 (2) and 75.7 (2)°, respectively. The corresponding dihedral angles in B are 85.5 (2), 3.8 (2), 2.4 (2) and 81.7 (2)°, respectively.

Related literature

For the pharmacological properties of imidazole derivatives, see: Hori et al. (2000[Hori, K., Sakaguchi, A., Kudoh, M., Ishida, K., Aoyama, Y. & Yoshida, Y. (2000). Chem. Pharm. Bull. 48, 60-64.]); Mamolo et al. (2004[Mamolo, M. G., Zampieri, D., Falagiani, V., Vio, L., Fermeglia, M., Ferrone, M., Pricl, S., Banfi, E. & Scialino, G. (2004). Arkivoc, pp. 231-250.]); Khabnadideh et al. (2003[Khabnadideh, S., Rezaeia, Z., Khalafi-Nezhadb, A., Bahrinajafia, R., Mohamadia, R. & Farrokhroza, A. A. (2003). Bioorg. Med. Chem. Lett. 13, 2863-2865.]). For the crystal structure of related 2-(4-fluoro­phen­yl)-1,4,5-triphenyl-1H-imidazole, see: Gayathri et al. (2010[Gayathri, P., Thiruvalluvar, A., Srinivasan, N., Jayabharathi, J. & Butcher, R. J. (2010). Acta Cryst. E66, o2519.]).

[Scheme 1]

Experimental

Crystal data
  • C27H20N2

  • Mr = 372.45

  • Triclinic, [P \overline 1]

  • a = 9.8169 (15) Å

  • b = 9.8846 (15) Å

  • c = 20.601 (3) Å

  • α = 81.133 (5)°

  • β = 82.922 (6)°

  • γ = 84.085 (6)°

  • V = 1952.9 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 113 K

  • 0.20 × 0.18 × 0.10 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.985, Tmax = 0.993

  • 25242 measured reflections

  • 9251 independent reflections

  • 6476 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.090

  • S = 0.98

  • 9251 reflections

  • 525 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information


Comment top

Imidazole derivatives exhibit various pharmacological properties, such as antifungal (Hori et al., 2000; Mamolo et al., 2004) and antibacterial (Khabnadideh et al., 2003) activities. The crystallographic structure of the similar imidazole compound had been reported . As the part of our research, the title compound 1,2,4,5-tetraphenyl-1H-imidazole was snythesized and its crystal structure was reported here.

The asymmetric unit of (I) contains two independent molecules (Fig. 1), A and B, respectively. All bond lengths and angles in (I) are normal and comparable with those observed in the related 2-(4-fluorophenyl)-1,4,5-triphenyl-1H-imidazole (Gayathri et al., 2010). In both independent molecules, atoms N2 (N4) (1-position) and C8 (C35) (5-position) are statistically disordered in the 0.571 (8):0.429 (8) and 0.736 (9):0.264 (9) ratios, respectively, in A and B. In A, the imidazole ring forms the dihedral angles of 84.3 (2), 21.6 (2), 21.5 (2) and 75.7 (2)°, respectively, with the phenyl rings in the 1-, 2-, 4- and 5-positions. The corresponding dihedral angles in B are 85.5 (2), 3.8 (2), 2.4 (2) and 81.7 (2)°, respectively.

Related literature top

For the pharmacological properties of imidazole derivatives, see: Hori et al. (2000); Mamolo et al. (2004); Khabnadideh et al. (2003). For the crystal structure of related 2-(4-fluorophenyl)-1,4,5-triphenyl-1H-imidazole, see: Gayathri et al. (2010).

Experimental top

The title compound was synthesized by the reaction of the benzaldehyde (1.1 g 10 mmol), aniline (1.0 g, 10 mmol), benzil (2.1 g, 10 mmol) and ammonium acetate (4.6 g, 10 mmol) in the refluxing ethanol (20 ml) for 5 days. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in ethanol:hexane (1:1).

Refinement top

All H atoms were positioned geometrically and refined as riding (C—H = 0.95 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq (parent).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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
[Figure 1] Fig. 1. Two independent molecules in (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 60% probability level. For the disordered atoms, only major components are shown.
1,2,4,5-Tetraphenyl-1H-imidazole top
Crystal data top
C27H20N2Z = 4
Mr = 372.45F(000) = 784
Triclinic, P1Dx = 1.267 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8169 (15) ÅCell parameters from 6569 reflections
b = 9.8846 (15) Åθ = 2.0–27.9°
c = 20.601 (3) ŵ = 0.07 mm1
α = 81.133 (5)°T = 113 K
β = 82.922 (6)°Prism, colourless
γ = 84.085 (6)°0.20 × 0.18 × 0.10 mm
V = 1952.9 (5) Å3
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
9251 independent reflections
Radiation source: rotating anode6476 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.037
Detector resolution: 14.22 pixels mm-1θmax = 27.9°, θmin = 2.0°
ϕ and ω scansh = 1212
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 1212
Tmin = 0.985, Tmax = 0.993l = 2727
25242 measured reflections
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0436P)2]
where P = (Fo2 + 2Fc2)/3
9251 reflections(Δ/σ)max = 0.001
525 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C27H20N2γ = 84.085 (6)°
Mr = 372.45V = 1952.9 (5) Å3
Triclinic, P1Z = 4
a = 9.8169 (15) ÅMo Kα radiation
b = 9.8846 (15) ŵ = 0.07 mm1
c = 20.601 (3) ÅT = 113 K
α = 81.133 (5)°0.20 × 0.18 × 0.10 mm
β = 82.922 (6)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
9251 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
6476 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.993Rint = 0.037
25242 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.090H-atom parameters constrained
S = 0.98Δρmax = 0.18 e Å3
9251 reflectionsΔρmin = 0.22 e Å3
525 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*/UeqOcc. (<1)
N10.80635 (8)1.15360 (8)0.43441 (4)0.02077 (19)
N20.75974 (9)0.95723 (9)0.49889 (4)0.0200 (2)0.571 (8)
C80.82664 (9)0.92421 (9)0.43964 (5)0.0209 (2)0.571 (8)
C8'0.75974 (9)0.95723 (9)0.49889 (4)0.0200 (2)0.429 (8)
N2'0.82664 (9)0.92421 (9)0.43964 (5)0.0209 (2)0.429 (8)
N30.29316 (8)0.79598 (8)0.00575 (4)0.02204 (19)
N40.46590 (9)0.70682 (9)0.06380 (4)0.0209 (2)0.736 (9)
C350.52319 (10)0.74836 (10)0.00029 (5)0.0218 (2)0.736 (9)
C35'0.46590 (9)0.70682 (9)0.06380 (4)0.0209 (2)0.264 (9)
N4'0.52319 (10)0.74836 (10)0.00029 (5)0.0218 (2)0.264 (9)
C10.90696 (11)1.20407 (11)0.29765 (5)0.0254 (2)
H10.84301.27120.31550.030*
C20.98019 (11)1.23762 (12)0.23614 (5)0.0294 (3)
H20.96661.32730.21230.035*
C31.07316 (11)1.14009 (12)0.20948 (5)0.0304 (3)
H31.12441.16320.16770.036*
C41.09098 (11)1.00934 (12)0.24388 (5)0.0298 (3)
H41.15330.94200.22520.036*
C51.01853 (11)0.97552 (11)0.30548 (5)0.0265 (2)
H51.03200.88520.32870.032*
C60.92601 (10)1.07277 (11)0.33370 (5)0.0218 (2)
C70.85347 (10)1.04719 (10)0.40096 (5)0.0204 (2)
C90.84989 (10)0.78221 (10)0.42550 (5)0.0203 (2)
C100.97511 (10)0.70703 (11)0.43514 (5)0.0257 (2)
H101.04590.74790.45070.031*
C110.99713 (11)0.57255 (11)0.42216 (5)0.0278 (2)
H111.08350.52190.42810.033*
C120.89327 (11)0.51213 (11)0.40059 (5)0.0274 (2)
H120.90790.41980.39190.033*
C130.76796 (11)0.58662 (11)0.39168 (5)0.0269 (2)
H130.69660.54470.37710.032*
C140.74547 (10)0.72159 (11)0.40371 (5)0.0238 (2)
H140.65950.77230.39710.029*
C150.71475 (10)0.85723 (10)0.55535 (5)0.0210 (2)
C160.57519 (11)0.84139 (11)0.57171 (5)0.0271 (2)
H160.51020.88690.54340.033*
C170.53132 (12)0.75874 (12)0.62969 (6)0.0316 (3)
H170.43600.74760.64110.038*
C180.62606 (12)0.69239 (11)0.67099 (6)0.0309 (3)
H180.59560.63810.71130.037*
C190.76538 (12)0.70531 (11)0.65341 (5)0.0297 (3)
H190.83050.65790.68120.036*
C200.81003 (11)0.78701 (11)0.59547 (5)0.0256 (2)
H200.90570.79490.58330.031*
C210.74965 (10)1.09806 (10)0.49433 (5)0.0197 (2)
C220.69161 (10)1.18380 (10)0.54532 (5)0.0202 (2)
C230.67869 (10)1.13582 (11)0.61297 (5)0.0238 (2)
H230.70251.04160.62820.029*
C240.63125 (11)1.22518 (11)0.65807 (5)0.0274 (2)
H240.62181.19140.70400.033*
C250.59758 (11)1.36258 (11)0.63704 (5)0.0264 (2)
H250.56581.42320.66830.032*
C260.61036 (11)1.41183 (11)0.56999 (5)0.0273 (2)
H260.58791.50650.55520.033*
C270.65588 (10)1.32298 (10)0.52461 (5)0.0241 (2)
H270.66301.35700.47870.029*
C280.28857 (10)0.91492 (10)0.12890 (5)0.0235 (2)
H280.20660.91580.09910.028*
C290.28205 (11)0.96577 (11)0.19530 (5)0.0259 (2)
H290.19590.99990.21060.031*
C300.40074 (11)0.96670 (11)0.23907 (5)0.0266 (2)
H300.39651.00100.28450.032*
C310.52586 (11)0.91717 (11)0.21611 (5)0.0267 (2)
H310.60780.91890.24590.032*
C320.53262 (11)0.86525 (11)0.15014 (5)0.0255 (2)
H320.61910.83100.13520.031*
C330.41349 (10)0.86257 (10)0.10519 (5)0.0207 (2)
C340.41416 (10)0.80371 (10)0.03502 (5)0.0207 (2)
C360.67340 (10)0.73485 (10)0.01793 (5)0.0220 (2)
C370.75036 (11)0.84435 (11)0.01528 (5)0.0274 (2)
H370.70600.92850.00350.033*
C380.89264 (12)0.82932 (12)0.03002 (5)0.0325 (3)
H380.94530.90400.02840.039*
C390.95823 (11)0.70780 (13)0.04689 (5)0.0337 (3)
H391.05570.69820.05600.040*
C400.88203 (12)0.59959 (12)0.05049 (6)0.0343 (3)
H400.92680.51610.06290.041*
C410.74000 (11)0.61332 (11)0.03586 (6)0.0293 (3)
H410.68780.53870.03810.035*
C420.54497 (10)0.64411 (10)0.11728 (5)0.0213 (2)
C430.58342 (11)0.50406 (11)0.12473 (5)0.0284 (2)
H430.56270.45020.09340.034*
C440.65214 (12)0.44297 (11)0.17803 (5)0.0308 (3)
H440.67880.34710.18340.037*
C450.68173 (11)0.52238 (11)0.22345 (5)0.0275 (2)
H450.72800.48060.26030.033*
C460.64419 (10)0.66234 (11)0.21547 (5)0.0259 (2)
H460.66480.71620.24690.031*
C470.57684 (10)0.72411 (11)0.16203 (5)0.0236 (2)
H470.55270.82040.15600.028*
C480.32554 (10)0.73797 (10)0.06543 (5)0.0214 (2)
C490.21973 (10)0.71348 (10)0.12231 (5)0.0224 (2)
C500.24418 (11)0.64767 (11)0.18527 (5)0.0300 (3)
H500.33540.61410.19380.036*
C510.13686 (11)0.63061 (12)0.23557 (6)0.0322 (3)
H510.15570.58730.27840.039*
C520.00356 (12)0.67575 (12)0.22413 (5)0.0318 (3)
H520.06970.66290.25860.038*
C530.02245 (12)0.74022 (13)0.16166 (6)0.0355 (3)
H530.11420.77130.15310.043*
C540.08427 (11)0.75956 (12)0.11180 (5)0.0304 (3)
H540.06490.80520.06950.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0220 (4)0.0206 (5)0.0197 (4)0.0017 (3)0.0024 (3)0.0027 (4)
N20.0189 (5)0.0193 (5)0.0218 (5)0.0015 (4)0.0022 (4)0.0030 (4)
C80.0201 (5)0.0198 (5)0.0230 (5)0.0011 (4)0.0028 (4)0.0035 (4)
C8'0.0189 (5)0.0193 (5)0.0218 (5)0.0015 (4)0.0022 (4)0.0030 (4)
N2'0.0201 (5)0.0198 (5)0.0230 (5)0.0011 (4)0.0028 (4)0.0035 (4)
N30.0240 (5)0.0212 (5)0.0203 (4)0.0004 (4)0.0027 (4)0.0024 (4)
N40.0224 (5)0.0193 (5)0.0208 (5)0.0005 (4)0.0037 (4)0.0029 (4)
C350.0237 (5)0.0201 (5)0.0218 (5)0.0006 (4)0.0037 (4)0.0042 (4)
C35'0.0224 (5)0.0193 (5)0.0208 (5)0.0005 (4)0.0037 (4)0.0029 (4)
N4'0.0237 (5)0.0201 (5)0.0218 (5)0.0006 (4)0.0037 (4)0.0042 (4)
C10.0253 (6)0.0275 (6)0.0231 (5)0.0008 (4)0.0038 (4)0.0038 (4)
C20.0293 (6)0.0335 (6)0.0239 (6)0.0019 (5)0.0049 (5)0.0016 (5)
C30.0255 (6)0.0440 (7)0.0210 (5)0.0031 (5)0.0027 (5)0.0022 (5)
C40.0241 (6)0.0383 (7)0.0270 (6)0.0024 (5)0.0013 (5)0.0093 (5)
C50.0258 (6)0.0273 (6)0.0263 (6)0.0000 (5)0.0037 (5)0.0050 (5)
C60.0206 (5)0.0252 (6)0.0208 (5)0.0030 (4)0.0046 (4)0.0049 (4)
C70.0193 (5)0.0200 (5)0.0226 (5)0.0020 (4)0.0042 (4)0.0033 (4)
C90.0222 (5)0.0200 (5)0.0177 (5)0.0023 (4)0.0003 (4)0.0007 (4)
C100.0218 (5)0.0234 (6)0.0314 (6)0.0032 (4)0.0041 (4)0.0011 (5)
C110.0253 (6)0.0245 (6)0.0307 (6)0.0034 (5)0.0011 (5)0.0001 (5)
C120.0360 (6)0.0213 (6)0.0242 (6)0.0015 (5)0.0014 (5)0.0053 (5)
C130.0292 (6)0.0292 (6)0.0243 (6)0.0068 (5)0.0033 (5)0.0072 (5)
C140.0219 (5)0.0278 (6)0.0216 (5)0.0009 (4)0.0028 (4)0.0037 (4)
C150.0228 (5)0.0190 (5)0.0225 (5)0.0023 (4)0.0013 (4)0.0072 (4)
C160.0236 (6)0.0259 (6)0.0331 (6)0.0023 (5)0.0040 (5)0.0074 (5)
C170.0268 (6)0.0316 (6)0.0370 (7)0.0084 (5)0.0050 (5)0.0098 (5)
C180.0425 (7)0.0226 (6)0.0276 (6)0.0071 (5)0.0033 (5)0.0067 (5)
C190.0367 (7)0.0235 (6)0.0297 (6)0.0001 (5)0.0087 (5)0.0045 (5)
C200.0227 (6)0.0244 (6)0.0304 (6)0.0009 (4)0.0030 (5)0.0070 (5)
C210.0179 (5)0.0193 (5)0.0222 (5)0.0014 (4)0.0044 (4)0.0026 (4)
C220.0167 (5)0.0215 (5)0.0228 (5)0.0033 (4)0.0018 (4)0.0035 (4)
C230.0271 (6)0.0211 (5)0.0229 (5)0.0028 (4)0.0044 (4)0.0006 (4)
C240.0341 (6)0.0281 (6)0.0201 (5)0.0055 (5)0.0013 (5)0.0034 (5)
C250.0269 (6)0.0259 (6)0.0274 (6)0.0030 (5)0.0016 (5)0.0100 (5)
C260.0290 (6)0.0209 (6)0.0308 (6)0.0012 (5)0.0002 (5)0.0044 (5)
C270.0264 (6)0.0220 (6)0.0223 (5)0.0003 (4)0.0004 (4)0.0011 (4)
C280.0223 (5)0.0244 (6)0.0233 (5)0.0016 (4)0.0013 (4)0.0030 (4)
C290.0275 (6)0.0246 (6)0.0264 (6)0.0010 (4)0.0078 (5)0.0029 (5)
C300.0360 (6)0.0251 (6)0.0189 (5)0.0039 (5)0.0046 (5)0.0022 (4)
C310.0279 (6)0.0285 (6)0.0231 (5)0.0027 (5)0.0025 (4)0.0055 (5)
C320.0240 (6)0.0271 (6)0.0250 (5)0.0012 (4)0.0025 (4)0.0051 (5)
C330.0244 (5)0.0178 (5)0.0204 (5)0.0014 (4)0.0031 (4)0.0043 (4)
C340.0217 (5)0.0181 (5)0.0230 (5)0.0006 (4)0.0026 (4)0.0059 (4)
C360.0246 (5)0.0236 (6)0.0177 (5)0.0001 (4)0.0053 (4)0.0014 (4)
C370.0347 (6)0.0267 (6)0.0216 (5)0.0040 (5)0.0042 (5)0.0038 (5)
C380.0334 (6)0.0393 (7)0.0262 (6)0.0141 (5)0.0060 (5)0.0003 (5)
C390.0239 (6)0.0457 (8)0.0280 (6)0.0015 (5)0.0028 (5)0.0048 (5)
C400.0301 (6)0.0326 (7)0.0372 (7)0.0057 (5)0.0022 (5)0.0025 (5)
C410.0268 (6)0.0249 (6)0.0358 (6)0.0008 (5)0.0036 (5)0.0044 (5)
C420.0197 (5)0.0227 (5)0.0209 (5)0.0005 (4)0.0021 (4)0.0026 (4)
C430.0359 (6)0.0235 (6)0.0277 (6)0.0002 (5)0.0084 (5)0.0074 (5)
C440.0383 (7)0.0215 (6)0.0320 (6)0.0037 (5)0.0088 (5)0.0021 (5)
C450.0286 (6)0.0299 (6)0.0229 (5)0.0002 (5)0.0056 (5)0.0001 (5)
C460.0269 (6)0.0293 (6)0.0227 (5)0.0033 (5)0.0032 (4)0.0071 (5)
C470.0252 (6)0.0218 (5)0.0235 (5)0.0008 (4)0.0011 (4)0.0045 (4)
C480.0227 (5)0.0193 (5)0.0223 (5)0.0008 (4)0.0045 (4)0.0041 (4)
C490.0252 (6)0.0203 (5)0.0219 (5)0.0020 (4)0.0022 (4)0.0039 (4)
C500.0262 (6)0.0331 (6)0.0279 (6)0.0009 (5)0.0035 (5)0.0039 (5)
C510.0341 (7)0.0344 (7)0.0254 (6)0.0049 (5)0.0023 (5)0.0047 (5)
C520.0291 (6)0.0372 (7)0.0268 (6)0.0048 (5)0.0035 (5)0.0016 (5)
C530.0244 (6)0.0491 (8)0.0304 (6)0.0021 (5)0.0016 (5)0.0025 (6)
C540.0279 (6)0.0396 (7)0.0221 (5)0.0022 (5)0.0041 (5)0.0015 (5)
Geometric parameters (Å, º) top
N1—C211.3490 (12)C24—C251.3794 (15)
N1—C71.3563 (13)C24—H240.9500
N2—C211.3748 (13)C25—C261.3870 (15)
N2—C81.3815 (12)C25—H250.9500
N2—C151.4607 (13)C26—C271.3836 (14)
C8—C71.3775 (13)C26—H260.9500
C8—C91.4666 (13)C27—H270.9500
N3—C481.3353 (12)C28—C291.3895 (14)
N3—C341.3694 (13)C28—C331.3961 (14)
N4—C481.3779 (13)C28—H280.9500
N4—C351.3875 (12)C29—C301.3826 (15)
N4—C421.4498 (13)C29—H290.9500
C35—C341.3800 (13)C30—C311.3857 (15)
C35—C361.4719 (14)C30—H300.9500
C1—C21.3883 (14)C31—C321.3839 (14)
C1—C61.3992 (14)C31—H310.9500
C1—H10.9500C32—C331.3993 (14)
C2—C31.3865 (15)C32—H320.9500
C2—H20.9500C33—C341.4732 (14)
C3—C41.3802 (15)C36—C411.3866 (14)
C3—H30.9500C36—C371.3936 (14)
C4—C51.3869 (15)C37—C381.3899 (15)
C4—H40.9500C37—H370.9500
C5—C61.3962 (14)C38—C391.3756 (16)
C5—H50.9500C38—H380.9500
C6—C71.4756 (14)C39—C401.3828 (16)
C9—C101.3890 (14)C39—H390.9500
C9—C141.3907 (14)C40—C411.3868 (15)
C10—C111.3861 (14)C40—H400.9500
C10—H100.9500C41—H410.9500
C11—C121.3830 (15)C42—C471.3856 (14)
C11—H110.9500C42—C431.3869 (14)
C12—C131.3844 (15)C43—C441.3854 (15)
C12—H120.9500C43—H430.9500
C13—C141.3848 (14)C44—C451.3845 (15)
C13—H130.9500C44—H440.9500
C14—H140.9500C45—C461.3844 (15)
C15—C201.3856 (14)C45—H450.9500
C15—C161.3890 (14)C46—C471.3823 (14)
C16—C171.3872 (15)C46—H460.9500
C16—H160.9500C47—H470.9500
C17—C181.3843 (16)C48—C491.4748 (14)
C17—H170.9500C49—C541.3922 (14)
C18—C191.3848 (15)C49—C501.3956 (14)
C18—H180.9500C50—C511.3878 (14)
C19—C201.3841 (15)C50—H500.9500
C19—H190.9500C51—C521.3749 (15)
C20—H200.9500C51—H510.9500
C21—C221.4744 (14)C52—C531.3865 (15)
C22—C231.3959 (14)C52—H520.9500
C22—C271.3979 (14)C53—C541.3801 (15)
C23—C241.3863 (14)C53—H530.9500
C23—H230.9500C54—H540.9500
C21—N1—C7106.53 (8)C26—C25—H25120.2
C21—N2—C8107.05 (8)C27—C26—C25119.92 (10)
C21—N2—C15128.13 (8)C27—C26—H26120.0
C8—N2—C15124.78 (8)C25—C26—H26120.0
C7—C8—N2106.16 (8)C26—C27—C22120.95 (10)
C7—C8—C9131.46 (9)C26—C27—H27119.5
N2—C8—C9122.27 (8)C22—C27—H27119.5
C48—N3—C34106.87 (8)C29—C28—C33121.15 (10)
C48—N4—C35107.27 (8)C29—C28—H28119.4
C48—N4—C42128.57 (9)C33—C28—H28119.4
C35—N4—C42124.16 (8)C30—C29—C28120.08 (10)
C34—C35—N4105.81 (9)C30—C29—H29120.0
C34—C35—C36133.24 (9)C28—C29—H29120.0
N4—C35—C36120.88 (9)C29—C30—C31119.47 (10)
C2—C1—C6120.93 (10)C29—C30—H30120.3
C2—C1—H1119.5C31—C30—H30120.3
C6—C1—H1119.5C32—C31—C30120.62 (10)
C3—C2—C1119.96 (11)C32—C31—H31119.7
C3—C2—H2120.0C30—C31—H31119.7
C1—C2—H2120.0C31—C32—C33120.72 (10)
C4—C3—C2119.75 (10)C31—C32—H32119.6
C4—C3—H3120.1C33—C32—H32119.6
C2—C3—H3120.1C28—C33—C32117.94 (10)
C3—C4—C5120.50 (10)C28—C33—C34119.13 (9)
C3—C4—H4119.7C32—C33—C34122.91 (9)
C5—C4—H4119.7N3—C34—C35109.90 (9)
C4—C5—C6120.68 (10)N3—C34—C33120.32 (9)
C4—C5—H5119.7C35—C34—C33129.77 (9)
C6—C5—H5119.7C41—C36—C37119.41 (10)
C5—C6—C1118.16 (10)C41—C36—C35120.82 (9)
C5—C6—C7123.56 (10)C37—C36—C35119.76 (9)
C1—C6—C7118.18 (9)C38—C37—C36119.42 (10)
N1—C7—C8110.23 (9)C38—C37—H37120.3
N1—C7—C6120.35 (9)C36—C37—H37120.3
C8—C7—C6129.38 (9)C39—C38—C37120.87 (10)
C10—C9—C14119.85 (10)C39—C38—H38119.6
C10—C9—C8120.13 (9)C37—C38—H38119.6
C14—C9—C8120.02 (9)C38—C39—C40119.88 (11)
C11—C10—C9120.27 (10)C38—C39—H39120.1
C11—C10—H10119.9C40—C39—H39120.1
C9—C10—H10119.9C39—C40—C41119.78 (11)
C12—C11—C10119.91 (10)C39—C40—H40120.1
C12—C11—H11120.0C41—C40—H40120.1
C10—C11—H11120.0C36—C41—C40120.64 (10)
C11—C12—C13119.79 (10)C36—C41—H41119.7
C11—C12—H12120.1C40—C41—H41119.7
C13—C12—H12120.1C47—C42—C43120.60 (10)
C12—C13—C14120.75 (10)C47—C42—N4119.48 (9)
C12—C13—H13119.6C43—C42—N4119.88 (9)
C14—C13—H13119.6C44—C43—C42119.79 (9)
C13—C14—C9119.42 (10)C44—C43—H43120.1
C13—C14—H14120.3C42—C43—H43120.1
C9—C14—H14120.3C45—C44—C43119.65 (10)
C20—C15—C16120.19 (10)C45—C44—H44120.2
C20—C15—N2119.91 (9)C43—C44—H44120.2
C16—C15—N2119.68 (9)C46—C45—C44120.33 (10)
C17—C16—C15119.61 (10)C46—C45—H45119.8
C17—C16—H16120.2C44—C45—H45119.8
C15—C16—H16120.2C47—C46—C45120.29 (10)
C18—C17—C16120.21 (10)C47—C46—H46119.9
C18—C17—H17119.9C45—C46—H46119.9
C16—C17—H17119.9C46—C47—C42119.33 (10)
C17—C18—C19119.88 (11)C46—C47—H47120.3
C17—C18—H18120.1C42—C47—H47120.3
C19—C18—H18120.1N3—C48—N4110.15 (9)
C20—C19—C18120.24 (11)N3—C48—C49121.94 (9)
C20—C19—H19119.9N4—C48—C49127.91 (9)
C18—C19—H19119.9C54—C49—C50117.67 (10)
C19—C20—C15119.79 (10)C54—C49—C48116.86 (9)
C19—C20—H20120.1C50—C49—C48125.47 (10)
C15—C20—H20120.1C51—C50—C49120.81 (10)
N1—C21—N2110.03 (8)C51—C50—H50119.6
N1—C21—C22121.72 (9)C49—C50—H50119.6
N2—C21—C22128.22 (9)C52—C51—C50120.71 (11)
C23—C22—C27118.47 (9)C52—C51—H51119.6
C23—C22—C21123.71 (9)C50—C51—H51119.6
C27—C22—C21117.69 (9)C51—C52—C53119.11 (10)
C24—C23—C22120.21 (10)C51—C52—H52120.4
C24—C23—H23119.9C53—C52—H52120.4
C22—C23—H23119.9C54—C53—C52120.37 (11)
C25—C24—C23120.77 (10)C54—C53—H53119.8
C25—C24—H24119.6C52—C53—H53119.8
C23—C24—H24119.6C53—C54—C49121.32 (10)
C24—C25—C26119.67 (10)C53—C54—H54119.3
C24—C25—H25120.2C49—C54—H54119.3
C21—N2—C8—C70.59 (11)C24—C25—C26—C270.41 (16)
C15—N2—C8—C7178.50 (9)C25—C26—C27—C221.04 (16)
C21—N2—C8—C9177.05 (8)C23—C22—C27—C260.80 (15)
C15—N2—C8—C95.04 (14)C21—C22—C27—C26175.23 (9)
C48—N4—C35—C340.15 (10)C33—C28—C29—C300.78 (15)
C42—N4—C35—C34179.23 (8)C28—C29—C30—C310.29 (15)
C48—N4—C35—C36177.31 (9)C29—C30—C31—C320.90 (16)
C42—N4—C35—C362.07 (14)C30—C31—C32—C330.46 (16)
C6—C1—C2—C30.37 (16)C29—C28—C33—C321.20 (15)
C1—C2—C3—C40.93 (16)C29—C28—C33—C34177.08 (9)
C2—C3—C4—C51.23 (16)C31—C32—C33—C280.58 (15)
C3—C4—C5—C60.23 (16)C31—C32—C33—C34177.62 (9)
C4—C5—C6—C11.04 (15)C48—N3—C34—C350.63 (11)
C4—C5—C6—C7175.23 (10)C48—N3—C34—C33179.57 (8)
C2—C1—C6—C51.34 (15)N4—C35—C34—N30.48 (11)
C2—C1—C6—C7175.14 (9)C36—C35—C34—N3177.14 (10)
C21—N1—C7—C80.01 (11)N4—C35—C34—C33179.29 (9)
C21—N1—C7—C6178.04 (9)C36—C35—C34—C334.06 (18)
N2—C8—C7—N10.36 (11)C28—C33—C34—N32.37 (14)
C9—C8—C7—N1176.37 (10)C32—C33—C34—N3175.81 (9)
N2—C8—C7—C6178.19 (10)C28—C33—C34—C35178.93 (10)
C9—C8—C7—C65.80 (18)C32—C33—C34—C352.88 (16)
C5—C6—C7—N1156.07 (9)C34—C35—C36—C4197.65 (14)
C1—C6—C7—N120.20 (14)N4—C35—C36—C4186.10 (12)
C5—C6—C7—C821.57 (16)C34—C35—C36—C3783.72 (14)
C1—C6—C7—C8162.16 (10)N4—C35—C36—C3792.53 (12)
C7—C8—C9—C1087.87 (14)C41—C36—C37—C380.65 (15)
N2—C8—C9—C1096.66 (12)C35—C36—C37—C38178.00 (9)
C7—C8—C9—C1493.46 (13)C36—C37—C38—C390.25 (16)
N2—C8—C9—C1482.00 (12)C37—C38—C39—C401.19 (17)
C14—C9—C10—C110.98 (15)C38—C39—C40—C411.21 (17)
C8—C9—C10—C11179.65 (9)C37—C36—C41—C400.62 (16)
C9—C10—C11—C121.08 (16)C35—C36—C41—C40178.02 (10)
C10—C11—C12—C130.38 (16)C39—C40—C41—C360.31 (17)
C11—C12—C13—C140.43 (16)C48—N4—C42—C4780.28 (13)
C12—C13—C14—C90.53 (15)C35—N4—C42—C4798.96 (11)
C10—C9—C14—C130.17 (15)C48—N4—C42—C4397.24 (12)
C8—C9—C14—C13178.84 (9)C35—N4—C42—C4383.52 (12)
C21—N2—C15—C20100.75 (12)C47—C42—C43—C441.16 (16)
C8—N2—C15—C2076.71 (12)N4—C42—C43—C44176.33 (9)
C21—N2—C15—C1673.93 (13)C42—C43—C44—C450.07 (17)
C8—N2—C15—C16108.61 (11)C43—C44—C45—C460.63 (16)
C20—C15—C16—C172.31 (15)C44—C45—C46—C470.03 (16)
N2—C15—C16—C17172.35 (9)C45—C46—C47—C421.24 (15)
C15—C16—C17—C180.01 (15)C43—C42—C47—C461.81 (15)
C16—C17—C18—C191.93 (16)N4—C42—C47—C46175.69 (9)
C17—C18—C19—C201.59 (16)C34—N3—C48—N40.53 (11)
C18—C19—C20—C150.70 (15)C34—N3—C48—C49179.85 (9)
C16—C15—C20—C192.65 (15)C35—N4—C48—N30.24 (11)
N2—C15—C20—C19172.00 (9)C42—N4—C48—N3179.58 (9)
C7—N1—C21—N20.39 (11)C35—N4—C48—C49179.83 (9)
C7—N1—C21—C22177.82 (9)C42—N4—C48—C490.83 (16)
C8—N2—C21—N10.62 (11)N3—C48—C49—C542.92 (14)
C15—N2—C21—N1178.44 (9)N4—C48—C49—C54177.54 (10)
C8—N2—C21—C22177.45 (9)N3—C48—C49—C50176.73 (10)
C15—N2—C21—C220.37 (16)N4—C48—C49—C502.81 (17)
N1—C21—C22—C23155.58 (10)C54—C49—C50—C510.73 (16)
N2—C21—C22—C2322.29 (16)C48—C49—C50—C51179.62 (10)
N1—C21—C22—C2720.22 (14)C49—C50—C51—C521.32 (17)
N2—C21—C22—C27161.91 (10)C50—C51—C52—C530.72 (17)
C27—C22—C23—C240.07 (15)C51—C52—C53—C540.42 (17)
C21—C22—C23—C24175.83 (9)C52—C53—C54—C491.01 (17)
C22—C23—C24—C250.69 (16)C50—C49—C54—C530.42 (16)
C23—C24—C25—C260.45 (16)C48—C49—C54—C53179.26 (10)

Experimental details

Crystal data
Chemical formulaC27H20N2
Mr372.45
Crystal system, space groupTriclinic, P1
Temperature (K)113
a, b, c (Å)9.8169 (15), 9.8846 (15), 20.601 (3)
α, β, γ (°)81.133 (5), 82.922 (6), 84.085 (6)
V3)1952.9 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.20 × 0.18 × 0.10
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.985, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
25242, 9251, 6476
Rint0.037
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.090, 0.98
No. of reflections9251
No. of parameters525
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.22

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

We gratefully acknowledge the support of the Science Fund for Young Scholars of Heilongjiang Province of China (grant No. QC2009C61) and the Program for Young Teachers' Scientific Research at Qiqihar University (grant No. 2010 K-M23).

References

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First citationHori, K., Sakaguchi, A., Kudoh, M., Ishida, K., Aoyama, Y. & Yoshida, Y. (2000). Chem. Pharm. Bull. 48, 60–64.  CrossRef PubMed CAS Google Scholar
First citationKhabnadideh, S., Rezaeia, Z., Khalafi-Nezhadb, A., Bahrinajafia, R., Mohamadia, R. & Farrokhroza, A. A. (2003). Bioorg. Med. Chem. Lett. 13, 2863–2865.  Web of Science CrossRef PubMed CAS Google Scholar
First citationMamolo, M. G., Zampieri, D., Falagiani, V., Vio, L., Fermeglia, M., Ferrone, M., Pricl, S., Banfi, E. & Scialino, G. (2004). Arkivoc, pp. 231–250.  CrossRef Google Scholar
First citationRigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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