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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 4| April 2013| Pages o527-o528

4-(1-Allyl-4,5-di­phenyl-1H-imidazol-2-yl)-N,N-di­methyl­aniline

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA, cChemistry Department, Faculty of Science, Minia University, El-Minia, Egypt, dChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, eManedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan, and fPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt
*Correspondence e-mail: shaabankamel@yahoo.com, akkurt@erciyes.edu.tr

(Received 25 February 2013; accepted 5 March 2013; online 9 March 2013)

The title compound, C26H25N3, crystallizes with four independent mol­ecules, 1–4, in the asymmetric unit of the triclinic unit cell. The allyl substituents on the imidazole rings adopt similar conformations in all four mol­ecules. The imadazole and the 4-and 5-substituted phenyl rings of two pairs of molecules in the asymmetric unit stack parallel to (110). In contrast, the dimethyl­aniline systems in these pairs of mol­ecules are almost normal to one another, with dihedral angles of 85.84 (10) and 85.65 (10)° between the benzene rings of the two dimethyl­aniline fragments of mol­ecules 1 and 2, and 3 and 4, respectively. The crystal structure features an extensive series of C—H⋯π inter­actions that link the mol­ecules into undulating rows along the c axis. The crystal studied was a pseudo-merohedral twin with twin law [-100, 0-10, 111] and the BASF parameter refined to 0.513 (3).

Related literature

For the synthesis and bioactivity of related heterocyclic mol­ecules, see: El-Sawy et al. (2012[El-Sawy, A. A., Mohamed, S. K., Eissa, A. M. F., Tantawy, A. H. & Issac, Y. A. (2012). J. Chem. Pharm. Res. 4, 2755-2762.]); Issac et al. (2012[Issac, Y. A., Mohamed, S. K., Eissa, A. M. F., Tantawy, A. H. & El-Sawy, A. A. (2012). J. Chem. Pharm. Res. 4, 2744-2750.]); Mohamed, Abdelhamid et al. (2012[Mohamed, S. K., Abdelhamid, A. A., Maharramov, A. M., Khalilov, A. N., Gurbanov, A. V. & Allahverdiyev, M. A. (2012). J. Chem. Pharm. Res. 4, 955-965.]); Soliman et al. (2012[Soliman, A. M., Mohamed, S. K., Elremaily, M. A. A. & Abdel-Ghany, H. (2012). Eur. J. Med. Chem. 47, 138-142.]). For the synthesis of a similar imidazole derivative, see: Mohamed, Akkurt et al. (2012[Mohamed, S. K., Akkurt, M., Fronczek, F. R., Marzouk, A. A. E. & Abdelhamid, A. A. (2012). Acta Cryst. E68, o2979-o2980.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C26H25N3

  • Mr = 379.49

  • Triclinic, [P \overline 1]

  • a = 9.4259 (7) Å

  • b = 10.2028 (7) Å

  • c = 44.721 (3) Å

  • α = 94.711 (2)°

  • β = 94.096 (2)°

  • γ = 107.359 (2)°

  • V = 4070.2 (5) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.57 mm−1

  • T = 90 K

  • 0.31 × 0.29 × 0.17 mm

Data collection
  • Bruker Kappa APEXII DUO diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.844, Tmax = 0.910

  • 26145 measured reflections

  • 13651 independent reflections

  • 13253 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.118

  • S = 1.03

  • 13651 reflections

  • 1054 parameters

  • 72 restraints

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg8, Cg6, Cg4, Cg10, Cg16, Cg14 and Cg12 are the centroids of the C4–C9, C47–C52, C30–C35, C21–C26, C56–C61, C99–C104, C82–C87 and C73–C78 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10ACg2i 0.98 2.71 3.514 (3) 139
C16—H16⋯Cg8 0.95 2.47 3.328 (3) 151
C37—H37ACg6ii 0.98 2.77 3.600 (2) 142
C42—H42⋯Cg4iii 0.95 2.49 3.345 (3) 150
C63—H63ACg10iv 0.98 2.73 3.595 (2) 147
C68—H68⋯Cg16 0.95 2.59 3.390 (3) 142
C88—H88CCg14v 0.98 2.74 3.509 (3) 136
C94—H94⋯Cg12iii 0.95 2.48 3.340 (3) 150
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+2, -y+1, -z; (iii) x+1, y+1, z; (iv) -x+1, -y+1, -z+1; (v) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Further to our studies on the synthesis of bioactive heterocyclic molecules such as pyrimidines and fused imidazole compounds (Soliman et al., 2012), thiadiazoles (Issac et al. 2012), acridinones and xanthenones (Mohamed, Abdelhamid et al., 2012), benzoxazinones and quinazolinones (El-Sawy et al., 2012), we report herein the crystal and molecular structure of the title compound.

Figure 1 shows molecule 1 and the numbering scheme,while Figure 2 identifies the four independent molecules in the asymmetric unit. The allyl substituents on the imidazole rings adopt similar conformations in all four molecules. The –N—C(H2)—C(H)—C(H2) torsion angles of the prop-1-ene substituent on the imidazole rings are -8.5 (3), 0.4 (4), -9.6 (4) and -1.3 (4)°, respectively, for molecules 1···4. Bond lengths and angles of these four independent molecules are comparable with each other and the bond lengths are similar to values reported in the literature (Allen et al., 1987).

All four of the unique molecules depart significantly from planarity. In molecule 1 (with N1), the central imidazole ring forms dihedral angles of 26.84 (12), 67.62 (13) and 27.15 (13)° with the C4–C9 benzene and C15–C20 and C21–C26 phenyl rings, respectively [the corresponding angles in molecule 2 (with N4) are 57.03 (12), 66.12 (14) and 26.74 (14)°; molecule 3 (with N7) 57.70 (11), 64.34 (13) and 27.27 (13)°, and molecule 4 (with N10) 26.85 (12), 69.03 (13) and 26.83 (12)°].

The imadazole and the 4- and 5-substituted phenyl rings of adjacent pairs of molecules stack parallel to (110). In contrast, the dimethylaniline systems in these pairs of molecules are almost normal to one another with dihedral angles of 85.84 (10)° between the C5···C9 and C30···C35 benzene rings of molecules 1 and 2 and 85.65 (10)° between the C56···C61 and C82···C87 benzene rings of molecules 3 and 4.

The crystal structure is stabilized by an extensive series of C—H···π interactions (Table 1), that link the molecules into undulating rows along the c axis. Figure 3 shows the crystal packing of the title compound along the b axis.

Related literature top

For the synthesis and bioactivity of related heterocyclic molecules, see: El-Sawy et al. (2012); Issac et al. (2012); Mohamed, Abdelhamid et al. (2012); Soliman et al. (2012). For the synthesis of a similar imidazole derivative, see: Mohamed, Akkurt et al. (2012). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared among series of imidazole derivatives according to our reported method (Mohamed, Akkurt et al., 2012). Suitable single crystals of (I) were obtained by the slow evaporation method using ethanol as a solvent. M.p. 403 – 405 K.

Refinement top

All H atoms were located geometrically and refined using a riding model with d(C—H) = 0.95–0.99 Å and, Uiso(methyl H) = 1.5 Ueq(C) and Uiso(H) = 1.2 Ueq(C) for other H atoms. The C12, C13, C14, C38, C39, C40, C64, C65, C66, C90, C91 and C92 atoms were refined anisotropically with the Uij values restrained to behave isotropically, with the ISOR instruction. The (0 - 1 10 and -1 - 1 1) reflections were probably affected by the beamstop and were omitted from the refinement. The structure was refined as a pseudo-merohedral twin with twin law [-1 0 0, 0 - 1 0, 1 1 1]. The final refined BASF value is 0.513 (3).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. An ORTEP view of one of the four molecules in the asymmetric unit of the title compound. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of the four unique molecules, 1···4, in the asymmetric unit of the title compound with the the N atoms numbered for identification purposes. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. All H atoms have been omitted for clarity.
[Figure 3] Fig. 3. A view of the crystal packing of the title compound along the b axis. All H atoms have been omitted for clarity.
4-(1-Allyl-4,5-diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline top
Crystal data top
C26H25N3Z = 8
Mr = 379.49F(000) = 1616
Triclinic, P1Dx = 1.239 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 9.4259 (7) ÅCell parameters from 9806 reflections
b = 10.2028 (7) Åθ = 4.6–67.5°
c = 44.721 (3) ŵ = 0.57 mm1
α = 94.711 (2)°T = 90 K
β = 94.096 (2)°Fragment, colourless
γ = 107.359 (2)°0.31 × 0.29 × 0.17 mm
V = 4070.2 (5) Å3
Data collection top
Bruker Kappa APEXII DUO
diffractometer
13651 independent reflections
Radiation source: IµS microfocus13253 reflections with I > 2σ(I)
QUAZAR multilayer optics monochromatorRint = 0.028
ϕ and ω scansθmax = 68.1°, θmin = 4.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1011
Tmin = 0.844, Tmax = 0.910k = 612
26145 measured reflectionsl = 5353
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0564P)2 + 1.1958P]
where P = (Fo2 + 2Fc2)/3
13651 reflections(Δ/σ)max = 0.001
1054 parametersΔρmax = 0.29 e Å3
72 restraintsΔρmin = 0.29 e Å3
Crystal data top
C26H25N3γ = 107.359 (2)°
Mr = 379.49V = 4070.2 (5) Å3
Triclinic, P1Z = 8
a = 9.4259 (7) ÅCu Kα radiation
b = 10.2028 (7) ŵ = 0.57 mm1
c = 44.721 (3) ÅT = 90 K
α = 94.711 (2)°0.31 × 0.29 × 0.17 mm
β = 94.096 (2)°
Data collection top
Bruker Kappa APEXII DUO
diffractometer
13651 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
13253 reflections with I > 2σ(I)
Tmin = 0.844, Tmax = 0.910Rint = 0.028
26145 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04372 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.03Δρmax = 0.29 e Å3
13651 reflectionsΔρmin = 0.29 e Å3
1054 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
N10.2373 (2)0.0763 (2)0.11871 (4)0.0225 (5)
N20.2148 (2)0.1476 (2)0.10855 (4)0.0214 (5)
N30.2954 (2)0.0143 (2)0.02847 (4)0.0318 (6)
C10.2128 (2)0.0195 (3)0.14483 (5)0.0218 (6)
C20.2006 (2)0.1205 (2)0.13908 (5)0.0188 (6)
C30.2368 (2)0.0300 (2)0.09676 (5)0.0212 (6)
C40.2551 (2)0.0165 (2)0.06473 (5)0.0229 (6)
C50.3112 (2)0.1115 (2)0.04883 (4)0.0255 (6)
C60.3242 (2)0.1122 (2)0.01854 (5)0.0275 (6)
C70.2839 (2)0.0157 (2)0.00186 (5)0.0272 (6)
C80.2299 (3)0.0816 (2)0.01796 (5)0.0305 (7)
C90.2160 (3)0.0794 (2)0.04828 (5)0.0294 (7)
C100.3390 (3)0.1217 (2)0.04546 (5)0.0338 (7)
C110.2454 (4)0.0836 (3)0.04489 (5)0.0426 (9)
C120.2655 (3)0.2194 (3)0.11544 (5)0.0293 (7)
C130.1396 (3)0.2691 (3)0.11371 (5)0.0326 (7)
C140.0106 (3)0.1854 (4)0.11112 (7)0.0455 (10)
C150.1976 (3)0.0965 (3)0.17334 (5)0.0204 (7)
C160.3228 (3)0.1963 (3)0.18926 (6)0.0266 (7)
C170.3100 (3)0.2654 (3)0.21664 (6)0.0342 (8)
C180.1747 (3)0.2333 (3)0.22898 (5)0.0271 (7)
C190.0506 (3)0.1338 (3)0.21314 (6)0.0301 (7)
C200.0635 (3)0.0657 (3)0.18609 (6)0.0271 (7)
C210.1826 (2)0.2274 (3)0.15890 (5)0.0235 (7)
C220.2333 (3)0.1946 (3)0.19014 (6)0.0245 (7)
C230.2137 (2)0.2950 (3)0.20945 (5)0.0241 (6)
C240.1430 (3)0.4351 (3)0.19829 (6)0.0289 (7)
C250.0963 (3)0.4674 (3)0.16783 (6)0.0247 (6)
C260.1177 (3)0.3648 (3)0.14864 (5)0.0242 (6)
N40.7512 (2)0.6001 (2)0.12200 (4)0.0209 (5)
N50.7198 (2)0.3771 (2)0.10856 (4)0.0233 (6)
N60.8391 (2)0.60149 (19)0.02239 (4)0.0297 (6)
C270.7197 (2)0.5349 (3)0.14697 (5)0.0217 (6)
C280.7030 (2)0.3949 (3)0.13924 (5)0.0214 (7)
C290.7482 (3)0.4988 (3)0.09882 (5)0.0242 (7)
C300.7712 (3)0.5301 (2)0.06782 (5)0.0253 (7)
C310.6640 (2)0.4604 (2)0.04421 (4)0.0236 (6)
C320.6854 (2)0.4832 (2)0.01452 (4)0.0245 (6)
C330.8168 (2)0.5775 (2)0.00714 (4)0.0242 (6)
C340.9247 (2)0.6485 (2)0.03105 (4)0.0256 (6)
C350.9023 (2)0.6255 (2)0.06057 (4)0.0246 (6)
C360.7416 (3)0.5088 (3)0.04678 (5)0.0340 (7)
C370.9868 (2)0.6789 (2)0.02920 (5)0.0319 (7)
C380.7531 (3)0.7391 (3)0.11852 (5)0.0330 (7)
C390.6072 (5)0.7582 (3)0.11284 (7)0.0582 (13)
C400.4714 (3)0.6564 (3)0.11080 (6)0.0381 (8)
C410.7057 (3)0.6071 (3)0.17633 (5)0.0215 (7)
C420.8321 (3)0.7035 (3)0.19241 (5)0.0240 (6)
C430.8207 (3)0.7712 (3)0.22014 (5)0.0296 (7)
C440.6851 (3)0.7409 (3)0.23226 (5)0.0274 (7)
C450.5594 (3)0.6443 (3)0.21616 (6)0.0319 (8)
C460.5707 (3)0.5774 (3)0.18895 (6)0.0287 (7)
C470.6799 (3)0.2826 (3)0.15742 (5)0.0244 (7)
C480.7280 (3)0.3056 (3)0.18890 (6)0.0272 (7)
C490.7047 (3)0.2001 (3)0.20674 (6)0.0301 (8)
C500.6320 (3)0.0621 (3)0.19375 (6)0.0318 (8)
C510.5880 (3)0.0386 (3)0.16323 (6)0.0294 (7)
C520.6133 (3)0.1470 (3)0.14535 (5)0.0269 (7)
N70.1237 (2)0.4775 (2)0.37921 (4)0.0237 (6)
N80.1092 (2)0.2697 (2)0.39208 (4)0.0223 (5)
N90.3624 (2)0.6246 (2)0.52295 (4)0.0296 (6)
C530.0650 (2)0.3835 (3)0.35288 (5)0.0215 (6)
C540.0609 (2)0.2603 (3)0.36195 (5)0.0210 (6)
C550.1460 (2)0.4029 (3)0.40159 (5)0.0202 (6)
C560.2035 (2)0.4637 (2)0.43285 (5)0.0215 (6)
C570.1198 (2)0.4171 (2)0.45651 (4)0.0249 (6)
C580.1709 (2)0.4695 (2)0.48622 (4)0.0250 (6)
C590.3097 (2)0.5707 (2)0.49347 (4)0.0245 (6)
C600.3935 (2)0.6186 (2)0.46961 (4)0.0261 (6)
C610.3402 (2)0.5655 (2)0.43999 (4)0.0249 (6)
C620.2913 (3)0.5566 (3)0.54715 (5)0.0357 (8)
C630.5181 (2)0.7089 (2)0.52963 (5)0.0318 (6)
C640.1307 (3)0.6229 (3)0.38245 (5)0.0285 (7)
C650.0166 (3)0.6434 (3)0.38863 (6)0.0370 (8)
C660.1441 (4)0.5484 (4)0.38728 (8)0.0576 (11)
C670.0223 (3)0.4310 (3)0.32416 (5)0.0217 (6)
C680.1276 (3)0.5165 (3)0.30879 (6)0.0273 (7)
C690.0867 (3)0.5522 (3)0.28131 (6)0.0305 (7)
C700.0601 (3)0.5072 (3)0.26886 (6)0.0306 (8)
C710.1656 (3)0.4231 (3)0.28393 (5)0.0311 (8)
C720.1276 (3)0.3864 (3)0.31209 (6)0.0291 (7)
C730.0208 (2)0.1250 (3)0.34245 (5)0.0218 (6)
C740.0372 (2)0.1210 (3)0.31201 (5)0.0232 (7)
C750.0043 (3)0.0062 (3)0.29449 (5)0.0295 (7)
C760.0585 (3)0.1265 (3)0.30642 (6)0.0312 (8)
C770.0748 (3)0.1243 (3)0.33720 (6)0.0319 (7)
C780.0350 (2)0.0003 (3)0.35543 (5)0.0248 (7)
N100.6152 (2)0.9552 (2)0.38150 (4)0.0214 (5)
N110.6021 (2)0.7439 (2)0.39089 (4)0.0229 (5)
N120.8247 (2)1.0142 (2)0.52795 (4)0.0344 (6)
C790.5611 (2)0.8690 (2)0.35378 (5)0.0201 (6)
C800.5576 (2)0.7430 (3)0.36100 (5)0.0229 (7)
C810.6361 (2)0.8744 (3)0.40265 (5)0.0227 (6)
C820.6905 (2)0.9192 (3)0.43469 (5)0.0255 (7)
C830.7593 (2)0.8385 (2)0.45046 (4)0.0268 (6)
C840.8034 (2)0.8686 (2)0.48108 (5)0.0282 (6)
C850.7808 (2)0.9826 (2)0.49751 (5)0.0276 (7)
C860.7106 (3)1.0622 (3)0.48165 (5)0.0299 (7)
C870.6651 (2)1.0298 (2)0.45109 (4)0.0288 (7)
C880.8852 (3)0.9236 (3)0.54479 (5)0.0352 (7)
C890.7915 (3)1.1269 (3)0.54418 (5)0.0420 (9)
C900.6479 (3)1.1060 (3)0.38405 (5)0.0273 (7)
C910.5167 (3)1.1531 (3)0.38677 (6)0.0328 (8)
C920.3790 (4)1.0781 (3)0.38664 (8)0.0510 (10)
C930.5231 (3)0.9231 (3)0.32560 (5)0.0213 (7)
C940.6311 (3)1.0059 (3)0.31025 (6)0.0298 (7)
C950.5938 (3)1.0464 (3)0.28294 (6)0.0303 (8)
C960.4471 (3)1.0081 (3)0.27067 (5)0.0292 (7)
C970.3384 (3)0.9272 (3)0.28552 (6)0.0318 (8)
C980.3734 (3)0.8861 (3)0.31346 (6)0.0296 (7)
C990.5169 (2)0.6121 (2)0.34015 (5)0.0188 (6)
C1000.5338 (2)0.6144 (3)0.30981 (5)0.0223 (7)
C1010.4907 (3)0.4902 (3)0.29093 (5)0.0281 (7)
C1020.4342 (3)0.3672 (3)0.30169 (5)0.0259 (7)
C1030.4192 (3)0.3623 (3)0.33246 (6)0.0267 (7)
C1040.4601 (2)0.4842 (3)0.35182 (5)0.0220 (6)
H50.341000.177400.059400.0310*
H60.361300.179300.008600.0330*
H80.202800.149700.007600.0370*
H90.178300.145700.058400.0350*
H10A0.435100.125600.036300.0510*
H10B0.348600.100600.066400.0510*
H10C0.262800.211100.045200.0510*
H11A0.138100.066600.043700.0640*
H11B0.264500.072400.066100.0640*
H11C0.299800.177900.036000.0640*
H12A0.336100.273200.132700.0350*
H12B0.316300.239000.096900.0350*
H130.158200.366200.114400.0390*
H14A0.033800.087900.110400.0550*
H14B0.088700.226500.110100.0550*
H160.416700.216700.181300.0320*
H170.394400.334700.226900.0410*
H180.166400.278300.247900.0330*
H190.043400.113100.221100.0360*
H200.021200.003700.176000.0320*
H220.281800.101000.197800.0290*
H230.247500.270500.230300.0290*
H240.128100.505500.211400.0350*
H250.049100.561000.160000.0300*
H260.086500.390100.127700.0290*
H310.574100.395700.048500.0280*
H320.610000.434200.001100.0290*
H341.014600.713400.026800.0310*
H350.976800.675200.076300.0290*
H36A0.639000.511300.045500.0510*
H36B0.745000.414500.045200.0510*
H36C0.774700.537800.066100.0510*
H37A1.060000.636200.021300.0480*
H37B1.012100.774300.019800.0480*
H37C0.988200.678500.051100.0480*
H38A0.812200.770900.101600.0400*
H38B0.805200.798900.137000.0400*
H390.605300.849200.110300.0700*
H40A0.467800.563800.113200.0460*
H40B0.381400.678900.107000.0460*
H420.925900.722800.184400.0290*
H430.906200.838100.230700.0350*
H440.677400.785300.251300.0330*
H450.465400.624800.224100.0380*
H460.485100.509900.178600.0340*
H480.777800.397300.197800.0330*
H490.737000.218800.227700.0360*
H500.614100.012300.205900.0380*
H510.539700.053200.154300.0350*
H520.583900.127300.124300.0320*
H570.025700.348000.452200.0300*
H580.111000.436400.501800.0300*
H600.487600.687900.473800.0310*
H610.398500.599600.424200.0300*
H62A0.182900.537000.543400.0540*
H62B0.327600.616400.566200.0540*
H62C0.314700.469700.548500.0540*
H63A0.583100.655800.522800.0480*
H63B0.540400.735300.551400.0480*
H63C0.535600.792200.519200.0480*
H64A0.162200.663500.363700.0340*
H64B0.207200.672700.399200.0340*
H650.015800.735700.394100.0440*
H66A0.150900.454500.381900.0690*
H66B0.230900.572500.391600.0690*
H680.228800.550900.317200.0330*
H690.160800.609000.270600.0370*
H700.087300.534400.250000.0370*
H710.266300.389100.275100.0370*
H720.202400.331800.322900.0350*
H740.076400.204100.303100.0280*
H750.005700.008400.273500.0350*
H760.085200.211800.294000.0370*
H770.113300.208500.345700.0380*
H780.045100.001800.376400.0300*
H830.776200.760700.439900.0320*
H840.849700.811200.491100.0340*
H860.693601.140300.492100.0360*
H870.615301.084800.441100.0350*
H88A0.807500.835200.545100.0530*
H88B0.919400.966900.565500.0530*
H88C0.969500.907800.535100.0530*
H89A0.849301.214100.537400.0630*
H89B0.817901.127900.565800.0630*
H89C0.684601.115600.540500.0630*
H90A0.720701.147100.401900.0330*
H90B0.695601.140800.366000.0330*
H910.534701.250200.388900.0390*
H92A0.354000.980200.384600.0610*
H92B0.302901.120900.388600.0610*
H940.732401.035300.318600.0360*
H950.670001.101400.272400.0360*
H960.421901.037900.252000.0350*
H970.237700.898300.276800.0380*
H980.296400.833500.324100.0360*
H1000.574300.699600.301800.0270*
H1010.501300.492300.270000.0340*
H1020.404800.284300.288400.0310*
H1030.381200.275900.340100.0320*
H1040.449900.481500.372800.0260*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0297 (9)0.0220 (10)0.0152 (9)0.0078 (8)0.0023 (7)0.0011 (7)
N20.0254 (9)0.0224 (10)0.0146 (9)0.0060 (7)0.0025 (7)0.0006 (7)
N30.0525 (12)0.0296 (11)0.0173 (9)0.0165 (9)0.0086 (8)0.0059 (7)
C10.0192 (10)0.0244 (12)0.0164 (10)0.0001 (8)0.0005 (8)0.0015 (9)
C20.0192 (9)0.0185 (11)0.0163 (10)0.0047 (8)0.0038 (8)0.0028 (8)
C30.0246 (10)0.0189 (11)0.0174 (10)0.0045 (8)0.0000 (8)0.0030 (8)
C40.0302 (11)0.0175 (11)0.0165 (10)0.0015 (9)0.0015 (8)0.0008 (8)
C50.0342 (11)0.0202 (11)0.0212 (10)0.0064 (9)0.0030 (8)0.0046 (8)
C60.0360 (11)0.0237 (11)0.0239 (10)0.0101 (9)0.0067 (8)0.0016 (8)
C70.0378 (12)0.0229 (11)0.0191 (10)0.0063 (9)0.0039 (8)0.0027 (8)
C80.0453 (13)0.0260 (12)0.0221 (10)0.0133 (10)0.0022 (9)0.0056 (9)
C90.0426 (12)0.0274 (12)0.0210 (10)0.0150 (10)0.0043 (8)0.0017 (8)
C100.0466 (13)0.0324 (13)0.0215 (10)0.0104 (10)0.0086 (9)0.0002 (9)
C110.0782 (19)0.0390 (15)0.0173 (11)0.0249 (14)0.0102 (11)0.0102 (10)
C120.0465 (13)0.0252 (13)0.0139 (10)0.0094 (10)0.0014 (9)0.0030 (9)
C130.0487 (14)0.0265 (12)0.0244 (11)0.0132 (11)0.0101 (10)0.0018 (10)
C140.0493 (16)0.0563 (19)0.0388 (14)0.0272 (14)0.0028 (12)0.0098 (13)
C150.0245 (11)0.0201 (12)0.0164 (11)0.0059 (9)0.0028 (8)0.0035 (9)
C160.0280 (11)0.0229 (12)0.0243 (11)0.0021 (10)0.0049 (10)0.0042 (10)
C170.0342 (13)0.0316 (14)0.0292 (13)0.0003 (11)0.0058 (10)0.0055 (11)
C180.0419 (13)0.0228 (13)0.0178 (11)0.0118 (10)0.0068 (10)0.0019 (9)
C190.0240 (11)0.0404 (15)0.0273 (12)0.0113 (10)0.0067 (9)0.0032 (11)
C200.0214 (11)0.0301 (14)0.0265 (12)0.0057 (10)0.0014 (9)0.0033 (10)
C210.0196 (10)0.0296 (13)0.0200 (11)0.0060 (9)0.0044 (9)0.0001 (10)
C220.0209 (10)0.0261 (13)0.0268 (12)0.0081 (9)0.0030 (9)0.0004 (10)
C230.0242 (10)0.0283 (13)0.0171 (10)0.0053 (9)0.0006 (8)0.0017 (9)
C240.0339 (12)0.0322 (14)0.0257 (12)0.0143 (10)0.0113 (9)0.0086 (10)
C250.0289 (11)0.0193 (11)0.0238 (11)0.0047 (9)0.0048 (9)0.0019 (9)
C260.0244 (10)0.0292 (13)0.0174 (10)0.0064 (9)0.0024 (8)0.0008 (9)
N40.0239 (9)0.0236 (10)0.0115 (8)0.0040 (7)0.0007 (6)0.0067 (7)
N50.0238 (9)0.0281 (11)0.0154 (9)0.0058 (8)0.0032 (7)0.0005 (8)
N60.0399 (10)0.0293 (11)0.0184 (9)0.0081 (8)0.0044 (7)0.0029 (7)
C270.0176 (9)0.0212 (11)0.0190 (11)0.0035 (8)0.0008 (8)0.0006 (9)
C280.0188 (10)0.0263 (13)0.0165 (11)0.0058 (9)0.0028 (8)0.0036 (9)
C290.0234 (10)0.0271 (13)0.0195 (11)0.0053 (9)0.0018 (8)0.0025 (9)
C300.0314 (11)0.0295 (13)0.0185 (10)0.0148 (10)0.0031 (8)0.0017 (9)
C310.0237 (10)0.0252 (12)0.0210 (10)0.0067 (8)0.0026 (7)0.0001 (8)
C320.0288 (10)0.0257 (12)0.0200 (10)0.0113 (9)0.0012 (8)0.0005 (8)
C330.0352 (11)0.0220 (11)0.0184 (10)0.0137 (9)0.0013 (8)0.0019 (8)
C340.0303 (10)0.0244 (11)0.0221 (10)0.0076 (9)0.0042 (8)0.0035 (8)
C350.0279 (10)0.0242 (11)0.0201 (10)0.0068 (9)0.0002 (8)0.0003 (8)
C360.0475 (13)0.0376 (14)0.0164 (10)0.0133 (11)0.0016 (9)0.0003 (10)
C370.0407 (12)0.0378 (13)0.0208 (10)0.0153 (10)0.0079 (8)0.0077 (9)
C380.0486 (14)0.0254 (13)0.0159 (11)0.0018 (11)0.0066 (10)0.0031 (9)
C390.120 (3)0.0402 (18)0.0378 (15)0.048 (2)0.0445 (18)0.0177 (14)
C400.0389 (13)0.0507 (16)0.0309 (12)0.0208 (12)0.0067 (10)0.0096 (11)
C410.0218 (10)0.0236 (13)0.0187 (11)0.0055 (9)0.0041 (8)0.0037 (9)
C420.0229 (10)0.0252 (12)0.0211 (11)0.0047 (9)0.0015 (9)0.0019 (9)
C430.0294 (12)0.0312 (14)0.0217 (11)0.0021 (10)0.0015 (9)0.0053 (10)
C440.0421 (13)0.0274 (14)0.0151 (10)0.0142 (11)0.0055 (9)0.0000 (9)
C450.0241 (11)0.0461 (17)0.0294 (13)0.0135 (11)0.0087 (10)0.0101 (12)
C460.0202 (11)0.0377 (15)0.0248 (11)0.0050 (10)0.0008 (9)0.0021 (11)
C470.0211 (10)0.0322 (14)0.0190 (11)0.0064 (9)0.0046 (9)0.0020 (10)
C480.0234 (11)0.0278 (14)0.0291 (13)0.0070 (10)0.0019 (10)0.0001 (11)
C490.0304 (12)0.0344 (15)0.0233 (12)0.0069 (10)0.0035 (10)0.0019 (10)
C500.0359 (13)0.0326 (14)0.0288 (12)0.0111 (11)0.0103 (10)0.0066 (11)
C510.0321 (11)0.0207 (12)0.0321 (13)0.0036 (10)0.0076 (10)0.0020 (10)
C520.0279 (11)0.0295 (13)0.0212 (11)0.0059 (10)0.0044 (9)0.0002 (10)
N70.0221 (9)0.0240 (11)0.0218 (9)0.0046 (7)0.0005 (7)0.0043 (8)
N80.0198 (8)0.0265 (11)0.0194 (9)0.0058 (7)0.0020 (7)0.0033 (8)
N90.0359 (10)0.0323 (11)0.0196 (9)0.0114 (8)0.0024 (7)0.0016 (7)
C530.0187 (10)0.0305 (13)0.0143 (10)0.0074 (9)0.0009 (8)0.0007 (9)
C540.0177 (9)0.0247 (12)0.0154 (10)0.0012 (8)0.0023 (8)0.0041 (9)
C550.0177 (9)0.0241 (12)0.0183 (10)0.0066 (8)0.0007 (8)0.0002 (8)
C560.0213 (10)0.0232 (12)0.0201 (10)0.0073 (9)0.0007 (8)0.0016 (8)
C570.0266 (10)0.0276 (12)0.0224 (10)0.0120 (9)0.0013 (8)0.0004 (8)
C580.0266 (10)0.0324 (13)0.0199 (10)0.0141 (9)0.0043 (8)0.0040 (8)
C590.0289 (10)0.0279 (12)0.0197 (10)0.0150 (9)0.0016 (8)0.0013 (8)
C600.0239 (10)0.0276 (12)0.0259 (10)0.0081 (8)0.0003 (8)0.0003 (8)
C610.0268 (10)0.0274 (11)0.0213 (10)0.0097 (9)0.0023 (8)0.0026 (8)
C620.0414 (13)0.0406 (15)0.0234 (11)0.0123 (11)0.0006 (9)0.0021 (11)
C630.0341 (11)0.0342 (12)0.0252 (10)0.0122 (10)0.0070 (8)0.0052 (9)
C640.0381 (12)0.0194 (12)0.0223 (11)0.0025 (10)0.0042 (9)0.0003 (9)
C650.0562 (17)0.0307 (14)0.0274 (12)0.0247 (13)0.0144 (11)0.0050 (10)
C660.0446 (16)0.059 (2)0.074 (2)0.0350 (15)0.0091 (15)0.0248 (17)
C670.0268 (11)0.0241 (12)0.0151 (10)0.0098 (9)0.0005 (8)0.0004 (9)
C680.0250 (11)0.0280 (13)0.0237 (11)0.0019 (10)0.0035 (9)0.0017 (10)
C690.0374 (13)0.0276 (13)0.0220 (11)0.0028 (11)0.0015 (10)0.0061 (10)
C700.0399 (13)0.0336 (15)0.0205 (11)0.0168 (11)0.0031 (10)0.0009 (10)
C710.0293 (12)0.0454 (16)0.0188 (11)0.0145 (11)0.0058 (9)0.0006 (11)
C720.0247 (11)0.0410 (15)0.0180 (11)0.0057 (11)0.0003 (9)0.0017 (10)
C730.0171 (9)0.0217 (12)0.0254 (11)0.0052 (8)0.0013 (9)0.0009 (10)
C740.0238 (11)0.0257 (13)0.0157 (10)0.0018 (9)0.0020 (8)0.0015 (10)
C750.0314 (12)0.0326 (14)0.0222 (12)0.0092 (10)0.0016 (9)0.0067 (10)
C760.0302 (12)0.0224 (13)0.0359 (14)0.0051 (10)0.0031 (10)0.0088 (10)
C770.0269 (11)0.0302 (14)0.0350 (13)0.0056 (10)0.0066 (10)0.0042 (11)
C780.0222 (10)0.0309 (13)0.0201 (11)0.0071 (9)0.0033 (8)0.0044 (9)
N100.0244 (9)0.0181 (10)0.0192 (9)0.0040 (7)0.0019 (7)0.0023 (7)
N110.0211 (8)0.0265 (11)0.0187 (9)0.0049 (7)0.0019 (7)0.0018 (8)
N120.0454 (11)0.0376 (12)0.0196 (9)0.0154 (9)0.0072 (8)0.0016 (8)
C790.0201 (10)0.0221 (12)0.0154 (10)0.0051 (9)0.0015 (8)0.0054 (9)
C800.0163 (9)0.0294 (14)0.0184 (11)0.0020 (9)0.0002 (8)0.0023 (10)
C810.0208 (10)0.0299 (13)0.0164 (10)0.0076 (9)0.0017 (8)0.0017 (9)
C820.0241 (10)0.0307 (14)0.0202 (10)0.0080 (9)0.0014 (8)0.0017 (9)
C830.0308 (11)0.0273 (12)0.0213 (10)0.0086 (9)0.0003 (8)0.0002 (8)
C840.0315 (11)0.0260 (12)0.0255 (10)0.0084 (9)0.0058 (8)0.0024 (8)
C850.0289 (11)0.0314 (13)0.0192 (10)0.0062 (9)0.0024 (8)0.0002 (9)
C860.0413 (13)0.0289 (13)0.0208 (10)0.0152 (10)0.0014 (9)0.0022 (9)
C870.0382 (12)0.0300 (13)0.0198 (10)0.0138 (10)0.0013 (8)0.0022 (8)
C880.0421 (13)0.0365 (14)0.0233 (11)0.0097 (11)0.0091 (9)0.0020 (9)
C890.0631 (17)0.0432 (16)0.0205 (11)0.0209 (14)0.0049 (10)0.0017 (10)
C900.0384 (12)0.0193 (12)0.0208 (11)0.0062 (10)0.0042 (9)0.0008 (9)
C910.0500 (14)0.0241 (13)0.0255 (12)0.0179 (11)0.0108 (10)0.0028 (10)
C920.0503 (17)0.0341 (16)0.079 (2)0.0255 (13)0.0181 (15)0.0077 (14)
C930.0282 (11)0.0188 (12)0.0174 (11)0.0089 (9)0.0014 (8)0.0006 (9)
C940.0257 (11)0.0309 (13)0.0256 (11)0.0002 (10)0.0063 (10)0.0022 (11)
C950.0390 (14)0.0230 (13)0.0242 (12)0.0021 (10)0.0004 (10)0.0065 (10)
C960.0400 (13)0.0300 (14)0.0190 (11)0.0159 (11)0.0041 (10)0.0024 (10)
C970.0318 (12)0.0438 (16)0.0195 (11)0.0143 (11)0.0060 (10)0.0004 (11)
C980.0259 (12)0.0409 (15)0.0194 (11)0.0066 (11)0.0025 (9)0.0014 (10)
C990.0163 (9)0.0184 (12)0.0202 (10)0.0047 (8)0.0010 (8)0.0022 (9)
C1000.0253 (11)0.0226 (13)0.0156 (10)0.0020 (9)0.0041 (9)0.0005 (10)
C1010.0299 (12)0.0303 (14)0.0225 (11)0.0097 (10)0.0024 (9)0.0072 (10)
C1020.0277 (11)0.0214 (12)0.0262 (11)0.0057 (9)0.0019 (9)0.0035 (9)
C1030.0221 (10)0.0241 (12)0.0323 (12)0.0063 (9)0.0028 (9)0.0013 (10)
C1040.0187 (10)0.0260 (12)0.0206 (10)0.0058 (9)0.0003 (8)0.0048 (9)
Geometric parameters (Å, º) top
N1—C11.350 (3)C37—H37A0.9800
N1—C31.401 (3)C38—H38B0.9900
N1—C121.426 (4)C38—H38A0.9900
N2—C21.395 (3)C39—H390.9500
N2—C31.316 (3)C40—H40A0.9500
N3—C71.369 (3)C40—H40B0.9500
N3—C101.457 (3)C42—H420.9500
N3—C111.453 (4)C43—H430.9500
N4—C271.353 (3)C44—H440.9500
N4—C291.395 (3)C45—H450.9500
N4—C381.434 (4)C46—H460.9500
N5—C291.308 (3)C48—H480.9500
N5—C281.396 (3)C49—H490.9500
N6—C331.382 (3)C50—H500.9500
N6—C361.448 (3)C51—H510.9500
N6—C371.449 (3)C52—H520.9500
N7—C531.420 (3)C53—C671.480 (3)
N7—C641.460 (4)C53—C541.343 (4)
N7—C551.348 (3)C54—C731.501 (4)
N8—C551.323 (3)C55—C561.477 (3)
N8—C541.377 (3)C56—C571.395 (3)
N9—C591.383 (3)C56—C611.389 (3)
N9—C621.432 (3)C57—C581.386 (3)
N9—C631.458 (3)C58—C591.400 (3)
N10—C811.346 (3)C59—C601.406 (3)
N10—C901.469 (4)C60—C611.388 (3)
N10—C791.426 (3)C64—C651.506 (4)
N11—C811.326 (3)C65—C661.293 (5)
N11—C801.371 (3)C67—C721.401 (4)
N12—C881.454 (3)C67—C681.378 (4)
N12—C851.377 (3)C68—C691.372 (4)
N12—C891.434 (3)C69—C701.380 (4)
C1—C21.399 (3)C70—C711.364 (4)
C1—C151.481 (3)C71—C721.396 (4)
C2—C211.440 (3)C73—C741.380 (3)
C3—C41.468 (3)C73—C781.414 (4)
C4—C51.404 (3)C74—C751.392 (4)
C4—C91.389 (3)C75—C761.351 (4)
C5—C61.368 (3)C76—C771.395 (4)
C6—C71.405 (3)C77—C781.387 (4)
C7—C81.414 (3)C57—H570.9500
C8—C91.373 (3)C58—H580.9500
C12—C131.423 (4)C60—H600.9500
C13—C141.409 (4)C61—H610.9500
C15—C161.407 (4)C62—H62B0.9800
C15—C201.385 (4)C62—H62C0.9800
C16—C171.393 (4)C62—H62A0.9800
C17—C181.385 (4)C63—H63B0.9800
C18—C191.398 (4)C63—H63C0.9800
C19—C201.376 (4)C63—H63A0.9800
C21—C221.423 (3)C64—H64A0.9900
C21—C261.376 (4)C64—H64B0.9900
C22—C231.373 (4)C65—H650.9500
C23—C241.415 (4)C66—H66A0.9500
C24—C251.383 (4)C66—H66B0.9500
C25—C261.385 (4)C68—H680.9500
C5—H50.9500C69—H690.9500
C6—H60.9500C70—H700.9500
C8—H80.9500C71—H710.9500
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C62—N9—C59—C60167.6 (2)N7—C55—C56—C6158.1 (3)
C62—N9—C59—C5813.8 (3)N8—C55—C56—C5756.7 (3)
C63—N9—C59—C58168.25 (18)C55—C56—C57—C58178.8 (2)
C63—N9—C59—C6013.1 (3)C55—C56—C61—C60178.4 (2)
C81—N10—C90—C91102.2 (3)C61—C56—C57—C580.4 (3)
C79—N10—C81—C82179.8 (2)C57—C56—C61—C600.7 (3)
C81—N10—C79—C93178.9 (2)C56—C57—C58—C590.6 (3)
C90—N10—C79—C80175.5 (2)C57—C58—C59—C601.1 (3)
C79—N10—C90—C9181.9 (3)C57—C58—C59—N9179.77 (19)
C90—N10—C81—C823.8 (4)C58—C59—C60—C610.7 (3)
C90—N10—C79—C934.4 (3)N9—C59—C60—C61179.43 (19)
C90—N10—C81—N11175.6 (2)C59—C60—C61—C560.2 (3)
C79—N10—C81—N110.8 (2)N7—C64—C65—C669.6 (4)
C81—N10—C79—C801.2 (2)C53—C67—C68—C69176.0 (3)
C80—N11—C81—C82179.5 (2)C53—C67—C72—C71175.3 (3)
C80—N11—C81—N100.1 (2)C68—C67—C72—C713.7 (4)
C81—N11—C80—C790.7 (3)C72—C67—C68—C693.0 (4)
C81—N11—C80—C99177.25 (19)C67—C68—C69—C701.9 (4)
C89—N12—C85—C84176.4 (2)C68—C69—C70—C711.5 (4)
C88—N12—C85—C845.2 (3)C69—C70—C71—C722.3 (4)
C89—N12—C85—C863.1 (3)C70—C71—C72—C673.4 (4)
C88—N12—C85—C86174.3 (2)C74—C73—C78—C771.1 (3)
N1—C1—C2—C21176.2 (2)C54—C73—C78—C77178.7 (2)
N1—C1—C15—C1671.0 (3)C54—C73—C74—C75178.6 (2)
C2—C1—C15—C2064.1 (4)C78—C73—C74—C751.2 (3)
C15—C1—C2—N2176.6 (2)C73—C74—C75—C760.9 (4)
C15—C1—C2—C215.8 (4)C74—C75—C76—C770.5 (4)
N1—C1—C15—C20113.6 (3)C75—C76—C77—C780.3 (4)
C2—C1—C15—C16111.3 (3)C76—C77—C78—C730.6 (4)
N1—C1—C2—N21.4 (2)C80—C79—C93—C94109.7 (3)
C1—C2—C21—C26154.8 (3)N10—C79—C93—C9470.2 (3)
N2—C2—C21—C2627.8 (3)C93—C79—C80—C993.3 (4)
N2—C2—C21—C22151.5 (2)N10—C79—C93—C98111.8 (3)
C1—C2—C21—C2225.9 (4)N10—C79—C80—C99176.6 (2)
N1—C3—C4—C5154.8 (2)C93—C79—C80—N11178.9 (2)
N2—C3—C4—C526.5 (3)C80—C79—C93—C9868.3 (4)
N2—C3—C4—C9150.8 (2)N10—C79—C80—N111.2 (2)
N1—C3—C4—C928.0 (3)N11—C80—C99—C10428.1 (3)
C5—C4—C9—C80.5 (3)C79—C80—C99—C104154.3 (2)
C3—C4—C5—C6176.21 (19)N11—C80—C99—C100152.0 (2)
C3—C4—C9—C8176.8 (2)C79—C80—C99—C10025.7 (3)
C9—C4—C5—C61.3 (3)N10—C81—C82—C8730.9 (4)
C4—C5—C6—C71.0 (3)N10—C81—C82—C83155.6 (2)
C5—C6—C7—C80.1 (3)N11—C81—C82—C8323.8 (3)
C5—C6—C7—N3179.8 (2)N11—C81—C82—C87149.8 (2)
N3—C7—C8—C9179.0 (2)C81—C82—C87—C86175.8 (2)
C6—C7—C8—C91.0 (3)C83—C82—C87—C862.2 (3)
C7—C8—C9—C40.6 (4)C87—C82—C83—C841.3 (3)
N1—C12—C13—C148.5 (3)C81—C82—C83—C84175.3 (2)
C1—C15—C16—C17177.7 (3)C82—C83—C84—C850.2 (3)
C16—C15—C20—C192.2 (4)C83—C84—C85—N12179.70 (19)
C1—C15—C20—C19177.7 (3)C83—C84—C85—C860.8 (3)
C20—C15—C16—C172.2 (4)N12—C85—C86—C87179.4 (2)
C15—C16—C17—C182.1 (4)C84—C85—C86—C870.1 (4)
C16—C17—C18—C191.9 (4)C85—C86—C87—C821.7 (4)
C17—C18—C19—C201.9 (4)N10—C90—C91—C921.3 (4)
C18—C19—C20—C152.1 (4)C79—C93—C94—C95175.1 (3)
C2—C21—C26—C25178.1 (2)C98—C93—C94—C952.9 (4)
C2—C21—C22—C23178.4 (2)C79—C93—C98—C97174.5 (2)
C26—C21—C22—C232.2 (4)C94—C93—C98—C973.5 (4)
C22—C21—C26—C252.6 (4)C93—C94—C95—C961.7 (4)
C21—C22—C23—C240.7 (4)C94—C95—C96—C971.2 (4)
C22—C23—C24—C250.6 (4)C95—C96—C97—C981.9 (4)
C23—C24—C25—C260.2 (4)C96—C97—C98—C933.1 (4)
C24—C25—C26—C211.4 (5)C80—C99—C100—C101178.3 (2)
N4—C27—C28—C47175.0 (2)C104—C99—C100—C1011.7 (3)
C41—C27—C28—N5177.1 (2)C80—C99—C104—C103178.7 (2)
N4—C27—C41—C4267.6 (3)C100—C99—C104—C1031.2 (3)
C41—C27—C28—C475.7 (4)C99—C100—C101—C1020.8 (4)
C28—C27—C41—C4664.2 (4)C100—C101—C102—C1030.7 (4)
C28—C27—C41—C42113.2 (3)C101—C102—C103—C1041.1 (4)
N4—C27—C28—N52.2 (2)C102—C103—C104—C990.2 (4)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg8, Cg6, Cg4, Cg10, Cg16, Cg14 and Cg12 are the centroids of the C4–C9, C47–C52, C30–C35, C21–C26, C56–C61, C99–C104, C82–C87 and C73–C78 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C66—H66A···N70.952.542.864 (4)100
C92—H92A···N100.952.562.876 (4)100
C10—H10A···Cg2i0.982.713.514 (3)139
C16—H16···Cg80.952.473.328 (3)151
C37—H37A···Cg6ii0.982.773.600 (2)142
C42—H42···Cg4iii0.952.493.345 (3)150
C63—H63A···Cg10iv0.982.733.595 (2)147
C68—H68···Cg160.952.593.390 (3)142
C88—H88C···Cg14v0.982.743.509 (3)136
C94—H94···Cg12iii0.952.483.340 (3)150
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1, z; (iii) x+1, y+1, z; (iv) x+1, y+1, z+1; (v) x+2, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC26H25N3
Mr379.49
Crystal system, space groupTriclinic, P1
Temperature (K)90
a, b, c (Å)9.4259 (7), 10.2028 (7), 44.721 (3)
α, β, γ (°)94.711 (2), 94.096 (2), 107.359 (2)
V3)4070.2 (5)
Z8
Radiation typeCu Kα
µ (mm1)0.57
Crystal size (mm)0.31 × 0.29 × 0.17
Data collection
DiffractometerBruker Kappa APEXII DUO
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.844, 0.910
No. of measured, independent and
observed [I > 2σ(I)] reflections
26145, 13651, 13253
Rint0.028
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.118, 1.03
No. of reflections13651
No. of parameters1054
No. of restraints72
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.29

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg2, Cg8, Cg6, Cg4, Cg10, Cg16, Cg14 and Cg12 are the centroids of the C4–C9, C47–C52, C30–C35, C21–C26, C56–C61, C99–C104, C82–C87 and C73–C78 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C10—H10A···Cg2i0.982.713.514 (3)139.0
C16—H16···Cg80.952.473.328 (3)151.0
C37—H37A···Cg6ii0.982.773.600 (2)142.0
C42—H42···Cg4iii0.952.493.345 (3)150.0
C63—H63A···Cg10iv0.982.733.595 (2)147.0
C68—H68···Cg160.952.593.390 (3)142.0
C88—H88C···Cg14v0.982.743.509 (3)136.0
C94—H94···Cg12iii0.952.483.340 (3)150.0
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1, z; (iii) x+1, y+1, z; (iv) x+1, y+1, z+1; (v) x+2, y+2, z+1.
 

Acknowledgements

Manchester Metropolitan University, Erciyes University and Louisiana State University are gratefully acknowledged for supporting this study.

References

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First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationEl-Sawy, A. A., Mohamed, S. K., Eissa, A. M. F., Tantawy, A. H. & Issac, Y. A. (2012). J. Chem. Pharm. Res. 4, 2755–2762.  CAS
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First citationMohamed, S. K., Akkurt, M., Fronczek, F. R., Marzouk, A. A. E. & Abdelhamid, A. A. (2012). Acta Cryst. E68, o2979–o2980.  CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSoliman, A. M., Mohamed, S. K., Elremaily, M. A. A. & Abdel-Ghany, H. (2012). Eur. J. Med. Chem. 47, 138–142.  Web of Science CrossRef CAS PubMed
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Volume 69| Part 4| April 2013| Pages o527-o528
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