Skip to main content
NCBI home page
Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Jan 31;68(Pt 2):o542. doi: 10.1107/S1600536812003145

1,2,4,5-Tetra­phenyl-1H-imidazole

Bing Zhao a, Zhi-yu Li a, Meng-jiao Fan a, Bo Song a, Qi-gang Deng a,*
PMCID: PMC3275280  PMID: 22347136

Abstract

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 ▶); 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 ▶).graphic file with name e-68-0o542-scheme1.jpg

Experimental

Crystal data

  • C27H20N2

  • M r = 372.45

  • Triclinic, Inline graphic

  • 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 ▶) T min = 0.985, T max = 0.993

  • 25242 measured reflections

  • 9251 independent reflections

  • 6476 reflections with I > 2σ(I)

  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037

  • wR(F 2) = 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 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003145/cv5236sup1.cif

e-68-0o542-sup1.cif (33.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003145/cv5236Isup2.hkl

e-68-0o542-Isup2.hkl (452.4KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812003145/cv5236Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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).

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

Fig. 1.

Fig. 1.

Open in a new tab

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.

Crystal data

C27H20N2 Z = 4
Mr = 372.45 F(000) = 784
Triclinic, P1 Dx = 1.267 Mg m−3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 9.8169 (15) Å Cell parameters from 6569 reflections
b = 9.8846 (15) Å θ = 2.0–27.9°
c = 20.601 (3) Å µ = 0.07 mm−1
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
Open in a new tab

Data collection

Rigaku Saturn CCD area-detector diffractometer 9251 independent reflections
Radiation source: rotating anode 6476 reflections with I > 2σ(I)
multilayer Rint = 0.037
Detector resolution: 14.22 pixels mm-1 θmax = 27.9°, θmin = 2.0°
φ and ω scans h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) k = −12→12
Tmin = 0.985, Tmax = 0.993 l = −27→27
25242 measured reflections
Open in a new tab

Refinement

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) = 0.090 H-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 parameters Δρmax = 0.18 e Å−3
0 restraints Δρmin = −0.22 e Å−3
Open in a new tab

Special details

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.
Open in a new tab

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
N1 0.80635 (8) 1.15360 (8) 0.43441 (4) 0.02077 (19)
N2 0.75974 (9) 0.95723 (9) 0.49889 (4) 0.0200 (2) 0.571 (8)
C8 0.82664 (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)
N3 0.29316 (8) 0.79598 (8) 0.00575 (4) 0.02204 (19)
N4 0.46590 (9) 0.70682 (9) 0.06380 (4) 0.0209 (2) 0.736 (9)
C35 0.52319 (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)
C1 0.90696 (11) 1.20407 (11) 0.29765 (5) 0.0254 (2)
H1 0.8430 1.2712 0.3155 0.030*
C2 0.98019 (11) 1.23762 (12) 0.23614 (5) 0.0294 (3)
H2 0.9666 1.3273 0.2123 0.035*
C3 1.07316 (11) 1.14009 (12) 0.20948 (5) 0.0304 (3)
H3 1.1244 1.1632 0.1677 0.036*
C4 1.09098 (11) 1.00934 (12) 0.24388 (5) 0.0298 (3)
H4 1.1533 0.9420 0.2252 0.036*
C5 1.01853 (11) 0.97552 (11) 0.30548 (5) 0.0265 (2)
H5 1.0320 0.8852 0.3287 0.032*
C6 0.92601 (10) 1.07277 (11) 0.33370 (5) 0.0218 (2)
C7 0.85347 (10) 1.04719 (10) 0.40096 (5) 0.0204 (2)
C9 0.84989 (10) 0.78221 (10) 0.42550 (5) 0.0203 (2)
C10 0.97511 (10) 0.70703 (11) 0.43514 (5) 0.0257 (2)
H10 1.0459 0.7479 0.4507 0.031*
C11 0.99713 (11) 0.57255 (11) 0.42216 (5) 0.0278 (2)
H11 1.0835 0.5219 0.4281 0.033*
C12 0.89327 (11) 0.51213 (11) 0.40059 (5) 0.0274 (2)
H12 0.9079 0.4198 0.3919 0.033*
C13 0.76796 (11) 0.58662 (11) 0.39168 (5) 0.0269 (2)
H13 0.6966 0.5447 0.3771 0.032*
C14 0.74547 (10) 0.72159 (11) 0.40371 (5) 0.0238 (2)
H14 0.6595 0.7723 0.3971 0.029*
C15 0.71475 (10) 0.85723 (10) 0.55535 (5) 0.0210 (2)
C16 0.57519 (11) 0.84139 (11) 0.57171 (5) 0.0271 (2)
H16 0.5102 0.8869 0.5434 0.033*
C17 0.53132 (12) 0.75874 (12) 0.62969 (6) 0.0316 (3)
H17 0.4360 0.7476 0.6411 0.038*
C18 0.62606 (12) 0.69239 (11) 0.67099 (6) 0.0309 (3)
H18 0.5956 0.6381 0.7113 0.037*
C19 0.76538 (12) 0.70531 (11) 0.65341 (5) 0.0297 (3)
H19 0.8305 0.6579 0.6812 0.036*
C20 0.81003 (11) 0.78701 (11) 0.59547 (5) 0.0256 (2)
H20 0.9057 0.7949 0.5833 0.031*
C21 0.74965 (10) 1.09806 (10) 0.49433 (5) 0.0197 (2)
C22 0.69161 (10) 1.18380 (10) 0.54532 (5) 0.0202 (2)
C23 0.67869 (10) 1.13582 (11) 0.61297 (5) 0.0238 (2)
H23 0.7025 1.0416 0.6282 0.029*
C24 0.63125 (11) 1.22518 (11) 0.65807 (5) 0.0274 (2)
H24 0.6218 1.1914 0.7040 0.033*
C25 0.59758 (11) 1.36258 (11) 0.63704 (5) 0.0264 (2)
H25 0.5658 1.4232 0.6683 0.032*
C26 0.61036 (11) 1.41183 (11) 0.56999 (5) 0.0273 (2)
H26 0.5879 1.5065 0.5552 0.033*
C27 0.65588 (10) 1.32298 (10) 0.52461 (5) 0.0241 (2)
H27 0.6630 1.3570 0.4787 0.029*
C28 0.28857 (10) 0.91492 (10) −0.12890 (5) 0.0235 (2)
H28 0.2066 0.9158 −0.0991 0.028*
C29 0.28205 (11) 0.96577 (11) −0.19530 (5) 0.0259 (2)
H29 0.1959 0.9999 −0.2106 0.031*
C30 0.40074 (11) 0.96670 (11) −0.23907 (5) 0.0266 (2)
H30 0.3965 1.0010 −0.2845 0.032*
C31 0.52586 (11) 0.91717 (11) −0.21611 (5) 0.0267 (2)
H31 0.6078 0.9189 −0.2459 0.032*
C32 0.53262 (11) 0.86525 (11) −0.15014 (5) 0.0255 (2)
H32 0.6191 0.8310 −0.1352 0.031*
C33 0.41349 (10) 0.86257 (10) −0.10519 (5) 0.0207 (2)
C34 0.41416 (10) 0.80371 (10) −0.03502 (5) 0.0207 (2)
C36 0.67340 (10) 0.73485 (10) −0.01793 (5) 0.0220 (2)
C37 0.75036 (11) 0.84435 (11) −0.01528 (5) 0.0274 (2)
H37 0.7060 0.9285 −0.0035 0.033*
C38 0.89264 (12) 0.82932 (12) −0.03002 (5) 0.0325 (3)
H38 0.9453 0.9040 −0.0284 0.039*
C39 0.95823 (11) 0.70780 (13) −0.04689 (5) 0.0337 (3)
H39 1.0557 0.6982 −0.0560 0.040*
C40 0.88203 (12) 0.59959 (12) −0.05049 (6) 0.0343 (3)
H40 0.9268 0.5161 −0.0629 0.041*
C41 0.74000 (11) 0.61332 (11) −0.03586 (6) 0.0293 (3)
H41 0.6878 0.5387 −0.0381 0.035*
C42 0.54497 (10) 0.64411 (10) 0.11728 (5) 0.0213 (2)
C43 0.58342 (11) 0.50406 (11) 0.12473 (5) 0.0284 (2)
H43 0.5627 0.4502 0.0934 0.034*
C44 0.65214 (12) 0.44297 (11) 0.17803 (5) 0.0308 (3)
H44 0.6788 0.3471 0.1834 0.037*
C45 0.68173 (11) 0.52238 (11) 0.22345 (5) 0.0275 (2)
H45 0.7280 0.4806 0.2603 0.033*
C46 0.64419 (10) 0.66234 (11) 0.21547 (5) 0.0259 (2)
H46 0.6648 0.7162 0.2469 0.031*
C47 0.57684 (10) 0.72411 (11) 0.16203 (5) 0.0236 (2)
H47 0.5527 0.8204 0.1560 0.028*
C48 0.32554 (10) 0.73797 (10) 0.06543 (5) 0.0214 (2)
C49 0.21973 (10) 0.71348 (10) 0.12231 (5) 0.0224 (2)
C50 0.24418 (11) 0.64767 (11) 0.18527 (5) 0.0300 (3)
H50 0.3354 0.6141 0.1938 0.036*
C51 0.13686 (11) 0.63061 (12) 0.23557 (6) 0.0322 (3)
H51 0.1557 0.5873 0.2784 0.039*
C52 0.00356 (12) 0.67575 (12) 0.22413 (5) 0.0318 (3)
H52 −0.0697 0.6629 0.2586 0.038*
C53 −0.02245 (12) 0.74022 (13) 0.16166 (6) 0.0355 (3)
H53 −0.1142 0.7713 0.1531 0.043*
C54 0.08427 (11) 0.75956 (12) 0.11180 (5) 0.0304 (3)
H54 0.0649 0.8052 0.0695 0.037*
Open in a new tab

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
N1 0.0220 (4) 0.0206 (5) 0.0197 (4) −0.0017 (3) −0.0024 (3) −0.0027 (4)
N2 0.0189 (5) 0.0193 (5) 0.0218 (5) −0.0015 (4) −0.0022 (4) −0.0030 (4)
C8 0.0201 (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)
N3 0.0240 (5) 0.0212 (5) 0.0203 (4) 0.0004 (4) −0.0027 (4) −0.0024 (4)
N4 0.0224 (5) 0.0193 (5) 0.0208 (5) 0.0005 (4) −0.0037 (4) −0.0029 (4)
C35 0.0237 (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)
C1 0.0253 (6) 0.0275 (6) 0.0231 (5) 0.0008 (4) −0.0038 (4) −0.0038 (4)
C2 0.0293 (6) 0.0335 (6) 0.0239 (6) −0.0019 (5) −0.0049 (5) 0.0016 (5)
C3 0.0255 (6) 0.0440 (7) 0.0210 (5) −0.0031 (5) −0.0027 (5) −0.0022 (5)
C4 0.0241 (6) 0.0383 (7) 0.0270 (6) 0.0024 (5) −0.0013 (5) −0.0093 (5)
C5 0.0258 (6) 0.0273 (6) 0.0263 (6) 0.0000 (5) −0.0037 (5) −0.0050 (5)
C6 0.0206 (5) 0.0252 (6) 0.0208 (5) −0.0030 (4) −0.0046 (4) −0.0049 (4)
C7 0.0193 (5) 0.0200 (5) 0.0226 (5) −0.0020 (4) −0.0042 (4) −0.0033 (4)
C9 0.0222 (5) 0.0200 (5) 0.0177 (5) −0.0023 (4) −0.0003 (4) −0.0007 (4)
C10 0.0218 (5) 0.0234 (6) 0.0314 (6) −0.0032 (4) −0.0041 (4) −0.0011 (5)
C11 0.0253 (6) 0.0245 (6) 0.0307 (6) 0.0034 (5) −0.0011 (5) −0.0001 (5)
C12 0.0360 (6) 0.0213 (6) 0.0242 (6) −0.0015 (5) 0.0014 (5) −0.0053 (5)
C13 0.0292 (6) 0.0292 (6) 0.0243 (6) −0.0068 (5) −0.0033 (5) −0.0072 (5)
C14 0.0219 (5) 0.0278 (6) 0.0216 (5) −0.0009 (4) −0.0028 (4) −0.0037 (4)
C15 0.0228 (5) 0.0190 (5) 0.0225 (5) −0.0023 (4) −0.0013 (4) −0.0072 (4)
C16 0.0236 (6) 0.0259 (6) 0.0331 (6) −0.0023 (5) −0.0040 (5) −0.0074 (5)
C17 0.0268 (6) 0.0316 (6) 0.0370 (7) −0.0084 (5) 0.0050 (5) −0.0098 (5)
C18 0.0425 (7) 0.0226 (6) 0.0276 (6) −0.0071 (5) 0.0033 (5) −0.0067 (5)
C19 0.0367 (7) 0.0235 (6) 0.0297 (6) −0.0001 (5) −0.0087 (5) −0.0045 (5)
C20 0.0227 (6) 0.0244 (6) 0.0304 (6) −0.0009 (4) −0.0030 (5) −0.0070 (5)
C21 0.0179 (5) 0.0193 (5) 0.0222 (5) −0.0014 (4) −0.0044 (4) −0.0026 (4)
C22 0.0167 (5) 0.0215 (5) 0.0228 (5) −0.0033 (4) −0.0018 (4) −0.0035 (4)
C23 0.0271 (6) 0.0211 (5) 0.0229 (5) −0.0028 (4) −0.0044 (4) −0.0006 (4)
C24 0.0341 (6) 0.0281 (6) 0.0201 (5) −0.0055 (5) −0.0013 (5) −0.0034 (5)
C25 0.0269 (6) 0.0259 (6) 0.0274 (6) −0.0030 (5) 0.0016 (5) −0.0100 (5)
C26 0.0290 (6) 0.0209 (6) 0.0308 (6) 0.0012 (5) −0.0002 (5) −0.0044 (5)
C27 0.0264 (6) 0.0220 (6) 0.0223 (5) −0.0003 (4) −0.0004 (4) −0.0011 (4)
C28 0.0223 (5) 0.0244 (6) 0.0233 (5) −0.0016 (4) −0.0013 (4) −0.0030 (4)
C29 0.0275 (6) 0.0246 (6) 0.0264 (6) −0.0010 (4) −0.0078 (5) −0.0029 (5)
C30 0.0360 (6) 0.0251 (6) 0.0189 (5) −0.0039 (5) −0.0046 (5) −0.0022 (4)
C31 0.0279 (6) 0.0285 (6) 0.0231 (5) −0.0027 (5) 0.0025 (4) −0.0055 (5)
C32 0.0240 (6) 0.0271 (6) 0.0250 (5) 0.0012 (4) −0.0025 (4) −0.0051 (5)
C33 0.0244 (5) 0.0178 (5) 0.0204 (5) −0.0014 (4) −0.0031 (4) −0.0043 (4)
C34 0.0217 (5) 0.0181 (5) 0.0230 (5) 0.0006 (4) −0.0026 (4) −0.0059 (4)
C36 0.0246 (5) 0.0236 (6) 0.0177 (5) 0.0001 (4) −0.0053 (4) −0.0014 (4)
C37 0.0347 (6) 0.0267 (6) 0.0216 (5) −0.0040 (5) −0.0042 (5) −0.0038 (5)
C38 0.0334 (6) 0.0393 (7) 0.0262 (6) −0.0141 (5) −0.0060 (5) 0.0003 (5)
C39 0.0239 (6) 0.0457 (8) 0.0280 (6) −0.0015 (5) −0.0028 (5) 0.0048 (5)
C40 0.0301 (6) 0.0326 (7) 0.0372 (7) 0.0057 (5) −0.0022 (5) −0.0025 (5)
C41 0.0268 (6) 0.0249 (6) 0.0358 (6) −0.0008 (5) −0.0036 (5) −0.0044 (5)
C42 0.0197 (5) 0.0227 (5) 0.0209 (5) −0.0005 (4) −0.0021 (4) −0.0026 (4)
C43 0.0359 (6) 0.0235 (6) 0.0277 (6) −0.0002 (5) −0.0084 (5) −0.0074 (5)
C44 0.0383 (7) 0.0215 (6) 0.0320 (6) 0.0037 (5) −0.0088 (5) −0.0021 (5)
C45 0.0286 (6) 0.0299 (6) 0.0229 (5) 0.0002 (5) −0.0056 (5) 0.0001 (5)
C46 0.0269 (6) 0.0293 (6) 0.0227 (5) −0.0033 (5) −0.0032 (4) −0.0071 (5)
C47 0.0252 (6) 0.0218 (5) 0.0235 (5) −0.0008 (4) −0.0011 (4) −0.0045 (4)
C48 0.0227 (5) 0.0193 (5) 0.0223 (5) 0.0008 (4) −0.0045 (4) −0.0041 (4)
C49 0.0252 (6) 0.0203 (5) 0.0219 (5) −0.0020 (4) −0.0022 (4) −0.0039 (4)
C50 0.0262 (6) 0.0331 (6) 0.0279 (6) −0.0009 (5) −0.0035 (5) 0.0039 (5)
C51 0.0341 (7) 0.0344 (7) 0.0254 (6) −0.0049 (5) −0.0023 (5) 0.0047 (5)
C52 0.0291 (6) 0.0372 (7) 0.0268 (6) −0.0048 (5) 0.0035 (5) −0.0016 (5)
C53 0.0244 (6) 0.0491 (8) 0.0304 (6) 0.0021 (5) −0.0016 (5) −0.0025 (6)
C54 0.0279 (6) 0.0396 (7) 0.0221 (5) 0.0022 (5) −0.0041 (5) −0.0015 (5)
Open in a new tab

Geometric parameters (Å, °)

N1—C21 1.3490 (12) C24—C25 1.3794 (15)
N1—C7 1.3563 (13) C24—H24 0.9500
N2—C21 1.3748 (13) C25—C26 1.3870 (15)
N2—C8 1.3815 (12) C25—H25 0.9500
N2—C15 1.4607 (13) C26—C27 1.3836 (14)
C8—C7 1.3775 (13) C26—H26 0.9500
C8—C9 1.4666 (13) C27—H27 0.9500
N3—C48 1.3353 (12) C28—C29 1.3895 (14)
N3—C34 1.3694 (13) C28—C33 1.3961 (14)
N4—C48 1.3779 (13) C28—H28 0.9500
N4—C35 1.3875 (12) C29—C30 1.3826 (15)
N4—C42 1.4498 (13) C29—H29 0.9500
C35—C34 1.3800 (13) C30—C31 1.3857 (15)
C35—C36 1.4719 (14) C30—H30 0.9500
C1—C2 1.3883 (14) C31—C32 1.3839 (14)
C1—C6 1.3992 (14) C31—H31 0.9500
C1—H1 0.9500 C32—C33 1.3993 (14)
C2—C3 1.3865 (15) C32—H32 0.9500
C2—H2 0.9500 C33—C34 1.4732 (14)
C3—C4 1.3802 (15) C36—C41 1.3866 (14)
C3—H3 0.9500 C36—C37 1.3936 (14)
C4—C5 1.3869 (15) C37—C38 1.3899 (15)
C4—H4 0.9500 C37—H37 0.9500
C5—C6 1.3962 (14) C38—C39 1.3756 (16)
C5—H5 0.9500 C38—H38 0.9500
C6—C7 1.4756 (14) C39—C40 1.3828 (16)
C9—C10 1.3890 (14) C39—H39 0.9500
C9—C14 1.3907 (14) C40—C41 1.3868 (15)
C10—C11 1.3861 (14) C40—H40 0.9500
C10—H10 0.9500 C41—H41 0.9500
C11—C12 1.3830 (15) C42—C47 1.3856 (14)
C11—H11 0.9500 C42—C43 1.3869 (14)
C12—C13 1.3844 (15) C43—C44 1.3854 (15)
C12—H12 0.9500 C43—H43 0.9500
C13—C14 1.3848 (14) C44—C45 1.3845 (15)
C13—H13 0.9500 C44—H44 0.9500
C14—H14 0.9500 C45—C46 1.3844 (15)
C15—C20 1.3856 (14) C45—H45 0.9500
C15—C16 1.3890 (14) C46—C47 1.3823 (14)
C16—C17 1.3872 (15) C46—H46 0.9500
C16—H16 0.9500 C47—H47 0.9500
C17—C18 1.3843 (16) C48—C49 1.4748 (14)
C17—H17 0.9500 C49—C54 1.3922 (14)
C18—C19 1.3848 (15) C49—C50 1.3956 (14)
C18—H18 0.9500 C50—C51 1.3878 (14)
C19—C20 1.3841 (15) C50—H50 0.9500
C19—H19 0.9500 C51—C52 1.3749 (15)
C20—H20 0.9500 C51—H51 0.9500
C21—C22 1.4744 (14) C52—C53 1.3865 (15)
C22—C23 1.3959 (14) C52—H52 0.9500
C22—C27 1.3979 (14) C53—C54 1.3801 (15)
C23—C24 1.3863 (14) C53—H53 0.9500
C23—H23 0.9500 C54—H54 0.9500
C21—N1—C7 106.53 (8) C26—C25—H25 120.2
C21—N2—C8 107.05 (8) C27—C26—C25 119.92 (10)
C21—N2—C15 128.13 (8) C27—C26—H26 120.0
C8—N2—C15 124.78 (8) C25—C26—H26 120.0
C7—C8—N2 106.16 (8) C26—C27—C22 120.95 (10)
C7—C8—C9 131.46 (9) C26—C27—H27 119.5
N2—C8—C9 122.27 (8) C22—C27—H27 119.5
C48—N3—C34 106.87 (8) C29—C28—C33 121.15 (10)
C48—N4—C35 107.27 (8) C29—C28—H28 119.4
C48—N4—C42 128.57 (9) C33—C28—H28 119.4
C35—N4—C42 124.16 (8) C30—C29—C28 120.08 (10)
C34—C35—N4 105.81 (9) C30—C29—H29 120.0
C34—C35—C36 133.24 (9) C28—C29—H29 120.0
N4—C35—C36 120.88 (9) C29—C30—C31 119.47 (10)
C2—C1—C6 120.93 (10) C29—C30—H30 120.3
C2—C1—H1 119.5 C31—C30—H30 120.3
C6—C1—H1 119.5 C32—C31—C30 120.62 (10)
C3—C2—C1 119.96 (11) C32—C31—H31 119.7
C3—C2—H2 120.0 C30—C31—H31 119.7
C1—C2—H2 120.0 C31—C32—C33 120.72 (10)
C4—C3—C2 119.75 (10) C31—C32—H32 119.6
C4—C3—H3 120.1 C33—C32—H32 119.6
C2—C3—H3 120.1 C28—C33—C32 117.94 (10)
C3—C4—C5 120.50 (10) C28—C33—C34 119.13 (9)
C3—C4—H4 119.7 C32—C33—C34 122.91 (9)
C5—C4—H4 119.7 N3—C34—C35 109.90 (9)
C4—C5—C6 120.68 (10) N3—C34—C33 120.32 (9)
C4—C5—H5 119.7 C35—C34—C33 129.77 (9)
C6—C5—H5 119.7 C41—C36—C37 119.41 (10)
C5—C6—C1 118.16 (10) C41—C36—C35 120.82 (9)
C5—C6—C7 123.56 (10) C37—C36—C35 119.76 (9)
C1—C6—C7 118.18 (9) C38—C37—C36 119.42 (10)
N1—C7—C8 110.23 (9) C38—C37—H37 120.3
N1—C7—C6 120.35 (9) C36—C37—H37 120.3
C8—C7—C6 129.38 (9) C39—C38—C37 120.87 (10)
C10—C9—C14 119.85 (10) C39—C38—H38 119.6
C10—C9—C8 120.13 (9) C37—C38—H38 119.6
C14—C9—C8 120.02 (9) C38—C39—C40 119.88 (11)
C11—C10—C9 120.27 (10) C38—C39—H39 120.1
C11—C10—H10 119.9 C40—C39—H39 120.1
C9—C10—H10 119.9 C39—C40—C41 119.78 (11)
C12—C11—C10 119.91 (10) C39—C40—H40 120.1
C12—C11—H11 120.0 C41—C40—H40 120.1
C10—C11—H11 120.0 C36—C41—C40 120.64 (10)
C11—C12—C13 119.79 (10) C36—C41—H41 119.7
C11—C12—H12 120.1 C40—C41—H41 119.7
C13—C12—H12 120.1 C47—C42—C43 120.60 (10)
C12—C13—C14 120.75 (10) C47—C42—N4 119.48 (9)
C12—C13—H13 119.6 C43—C42—N4 119.88 (9)
C14—C13—H13 119.6 C44—C43—C42 119.79 (9)
C13—C14—C9 119.42 (10) C44—C43—H43 120.1
C13—C14—H14 120.3 C42—C43—H43 120.1
C9—C14—H14 120.3 C45—C44—C43 119.65 (10)
C20—C15—C16 120.19 (10) C45—C44—H44 120.2
C20—C15—N2 119.91 (9) C43—C44—H44 120.2
C16—C15—N2 119.68 (9) C46—C45—C44 120.33 (10)
C17—C16—C15 119.61 (10) C46—C45—H45 119.8
C17—C16—H16 120.2 C44—C45—H45 119.8
C15—C16—H16 120.2 C47—C46—C45 120.29 (10)
C18—C17—C16 120.21 (10) C47—C46—H46 119.9
C18—C17—H17 119.9 C45—C46—H46 119.9
C16—C17—H17 119.9 C46—C47—C42 119.33 (10)
C17—C18—C19 119.88 (11) C46—C47—H47 120.3
C17—C18—H18 120.1 C42—C47—H47 120.3
C19—C18—H18 120.1 N3—C48—N4 110.15 (9)
C20—C19—C18 120.24 (11) N3—C48—C49 121.94 (9)
C20—C19—H19 119.9 N4—C48—C49 127.91 (9)
C18—C19—H19 119.9 C54—C49—C50 117.67 (10)
C19—C20—C15 119.79 (10) C54—C49—C48 116.86 (9)
C19—C20—H20 120.1 C50—C49—C48 125.47 (10)
C15—C20—H20 120.1 C51—C50—C49 120.81 (10)
N1—C21—N2 110.03 (8) C51—C50—H50 119.6
N1—C21—C22 121.72 (9) C49—C50—H50 119.6
N2—C21—C22 128.22 (9) C52—C51—C50 120.71 (11)
C23—C22—C27 118.47 (9) C52—C51—H51 119.6
C23—C22—C21 123.71 (9) C50—C51—H51 119.6
C27—C22—C21 117.69 (9) C51—C52—C53 119.11 (10)
C24—C23—C22 120.21 (10) C51—C52—H52 120.4
C24—C23—H23 119.9 C53—C52—H52 120.4
C22—C23—H23 119.9 C54—C53—C52 120.37 (11)
C25—C24—C23 120.77 (10) C54—C53—H53 119.8
C25—C24—H24 119.6 C52—C53—H53 119.8
C23—C24—H24 119.6 C53—C54—C49 121.32 (10)
C24—C25—C26 119.67 (10) C53—C54—H54 119.3
C24—C25—H25 120.2 C49—C54—H54 119.3
C21—N2—C8—C7 −0.59 (11) C24—C25—C26—C27 0.41 (16)
C15—N2—C8—C7 −178.50 (9) C25—C26—C27—C22 −1.04 (16)
C21—N2—C8—C9 −177.05 (8) C23—C22—C27—C26 0.80 (15)
C15—N2—C8—C9 5.04 (14) C21—C22—C27—C26 −175.23 (9)
C48—N4—C35—C34 0.15 (10) C33—C28—C29—C30 −0.78 (15)
C42—N4—C35—C34 −179.23 (8) C28—C29—C30—C31 −0.29 (15)
C48—N4—C35—C36 177.31 (9) C29—C30—C31—C32 0.90 (16)
C42—N4—C35—C36 −2.07 (14) C30—C31—C32—C33 −0.46 (16)
C6—C1—C2—C3 0.37 (16) C29—C28—C33—C32 1.20 (15)
C1—C2—C3—C4 0.93 (16) C29—C28—C33—C34 −177.08 (9)
C2—C3—C4—C5 −1.23 (16) C31—C32—C33—C28 −0.58 (15)
C3—C4—C5—C6 0.23 (16) C31—C32—C33—C34 177.62 (9)
C4—C5—C6—C1 1.04 (15) C48—N3—C34—C35 0.63 (11)
C4—C5—C6—C7 −175.23 (10) C48—N3—C34—C33 179.57 (8)
C2—C1—C6—C5 −1.34 (15) N4—C35—C34—N3 −0.48 (11)
C2—C1—C6—C7 175.14 (9) C36—C35—C34—N3 −177.14 (10)
C21—N1—C7—C8 0.01 (11) N4—C35—C34—C33 −179.29 (9)
C21—N1—C7—C6 −178.04 (9) C36—C35—C34—C33 4.06 (18)
N2—C8—C7—N1 0.36 (11) C28—C33—C34—N3 2.37 (14)
C9—C8—C7—N1 176.37 (10) C32—C33—C34—N3 −175.81 (9)
N2—C8—C7—C6 178.19 (10) C28—C33—C34—C35 −178.93 (10)
C9—C8—C7—C6 −5.80 (18) C32—C33—C34—C35 2.88 (16)
C5—C6—C7—N1 156.07 (9) C34—C35—C36—C41 −97.65 (14)
C1—C6—C7—N1 −20.20 (14) N4—C35—C36—C41 86.10 (12)
C5—C6—C7—C8 −21.57 (16) C34—C35—C36—C37 83.72 (14)
C1—C6—C7—C8 162.16 (10) N4—C35—C36—C37 −92.53 (12)
C7—C8—C9—C10 87.87 (14) C41—C36—C37—C38 −0.65 (15)
N2—C8—C9—C10 −96.66 (12) C35—C36—C37—C38 178.00 (9)
C7—C8—C9—C14 −93.46 (13) C36—C37—C38—C39 −0.25 (16)
N2—C8—C9—C14 82.00 (12) C37—C38—C39—C40 1.19 (17)
C14—C9—C10—C11 0.98 (15) C38—C39—C40—C41 −1.21 (17)
C8—C9—C10—C11 179.65 (9) C37—C36—C41—C40 0.62 (16)
C9—C10—C11—C12 −1.08 (16) C35—C36—C41—C40 −178.02 (10)
C10—C11—C12—C13 0.38 (16) C39—C40—C41—C36 0.31 (17)
C11—C12—C13—C14 0.43 (16) C48—N4—C42—C47 −80.28 (13)
C12—C13—C14—C9 −0.53 (15) C35—N4—C42—C47 98.96 (11)
C10—C9—C14—C13 −0.17 (15) C48—N4—C42—C43 97.24 (12)
C8—C9—C14—C13 −178.84 (9) C35—N4—C42—C43 −83.52 (12)
C21—N2—C15—C20 −100.75 (12) C47—C42—C43—C44 1.16 (16)
C8—N2—C15—C20 76.71 (12) N4—C42—C43—C44 −176.33 (9)
C21—N2—C15—C16 73.93 (13) C42—C43—C44—C45 0.07 (17)
C8—N2—C15—C16 −108.61 (11) C43—C44—C45—C46 −0.63 (16)
C20—C15—C16—C17 2.31 (15) C44—C45—C46—C47 −0.03 (16)
N2—C15—C16—C17 −172.35 (9) C45—C46—C47—C42 1.24 (15)
C15—C16—C17—C18 −0.01 (15) C43—C42—C47—C46 −1.81 (15)
C16—C17—C18—C19 −1.93 (16) N4—C42—C47—C46 175.69 (9)
C17—C18—C19—C20 1.59 (16) C34—N3—C48—N4 −0.53 (11)
C18—C19—C20—C15 0.70 (15) C34—N3—C48—C49 179.85 (9)
C16—C15—C20—C19 −2.65 (15) C35—N4—C48—N3 0.24 (11)
N2—C15—C20—C19 172.00 (9) C42—N4—C48—N3 179.58 (9)
C7—N1—C21—N2 −0.39 (11) C35—N4—C48—C49 179.83 (9)
C7—N1—C21—C22 177.82 (9) C42—N4—C48—C49 −0.83 (16)
C8—N2—C21—N1 0.62 (11) N3—C48—C49—C54 −2.92 (14)
C15—N2—C21—N1 178.44 (9) N4—C48—C49—C54 177.54 (10)
C8—N2—C21—C22 −177.45 (9) N3—C48—C49—C50 176.73 (10)
C15—N2—C21—C22 0.37 (16) N4—C48—C49—C50 −2.81 (17)
N1—C21—C22—C23 −155.58 (10) C54—C49—C50—C51 −0.73 (16)
N2—C21—C22—C23 22.29 (16) C48—C49—C50—C51 179.62 (10)
N1—C21—C22—C27 20.22 (14) C49—C50—C51—C52 1.32 (17)
N2—C21—C22—C27 −161.91 (10) C50—C51—C52—C53 −0.72 (17)
C27—C22—C23—C24 0.07 (15) C51—C52—C53—C54 −0.42 (17)
C21—C22—C23—C24 175.83 (9) C52—C53—C54—C49 1.01 (17)
C22—C23—C24—C25 −0.69 (16) C50—C49—C54—C53 −0.42 (16)
C23—C24—C25—C26 0.45 (16) C48—C49—C54—C53 179.26 (10)
Open in a new tab

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5236).

References

  1. Gayathri, P., Thiruvalluvar, A., Srinivasan, N., Jayabharathi, J. & Butcher, R. J. (2010). Acta Cryst. E66, o2519. [DOI] [PMC free article] [PubMed]
  2. Hori, K., Sakaguchi, A., Kudoh, M., Ishida, K., Aoyama, Y. & Yoshida, Y. (2000). Chem. Pharm. Bull. 48, 60–64. [DOI] [PubMed]
  3. Khabnadideh, S., Rezaeia, Z., Khalafi-Nezhadb, A., Bahrinajafia, R., Mohamadia, R. & Farrokhroza, A. A. (2003). Bioorg. Med. Chem. Lett. 13, 2863–2865. [DOI] [PubMed]
  4. Mamolo, M. G., Zampieri, D., Falagiani, V., Vio, L., Fermeglia, M., Ferrone, M., Pricl, S., Banfi, E. & Scialino, G. (2004). Arkivoc, pp. 231–250.
  5. Rigaku/MSC (2005). CrystalClear Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
  6. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003145/cv5236sup1.cif

e-68-0o542-sup1.cif (33.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003145/cv5236Isup2.hkl

e-68-0o542-Isup2.hkl (452.4KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812003145/cv5236Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

RESOURCES