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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 11| November 2012| Pages o3113-o3114
doi:10.1107/S1600536812041979

2-(4-Meth­­oxy­phen­yl)-4,5-di­phenyl-1-(prop-2-en-1-yl)-1H-imidazole

Mehmet Akkurt,a* Adel A. Marzouk,b Vagif. M. Abbasov,c Antar A. Abdelhamidd and Atash V. Gurbanovd

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt, cMamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan, and dDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 5 October 2012; accepted 7 October 2012; online 13 October 2012)

The asymmetric unit of the title compound, C25H22N2O, contains two independent mol­ecules (A and B), with significantly different conformations. In mol­ecule A, the central imidazole ring makes dihedral angles of 88.26 (10) and 12.74 (11)° with the two phenyl rings, and 22.06 (9)° with the benzene ring. In mol­ecule B, one of the phenyl rings is disordered over two sites, each having an occupancy of 0.5. Here the central imidazole ring forms dihedral angles of 79.24 (10)° with the ordered phenyl ring, and 3.5 (5) and 22.6 (5)° with the two parts of the disordered phenyl ring. The dihedral angle involving the benzene ring is 67.49 (10)°. The —N—C(H2)—C(H)—C(H2) torsion angles of the prop-1-ene group in the two mol­ecules are very similar, 0.5 (3) and 1.3 (4)° for mol­ecules A and B, respectively. The crystal structure is stabilized by C—H⋯π inter­actions.

Related literature

For the synthesis, see: Mohamed 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 biological properties of imidazoles, see: Puratchikody & Doble (2007[Puratchikody, A. & Doble, M. (2007). Bioorg. Med. Chem. Lett. 15, 1083-1090.]); Bhatnagar et al. (2011[Bhatnagar, A., Sharma, P. K. & Kumar, N. (2011). Int. J. Pharm. Tech. Res. 3, 268-282.]); Antolini et al. (1999[Antolini, M., Bozzoli, A. & Ghiron, C. (1999). Bioorg. Med. Chem. Lett. 9, 1023-1028.]); Wang et al. (2002[Wang, L., Woods, K. W. & Li, Q. (2002). J. Med. Chem. 45, 1697-1711.]). For standard 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

  • C25H22N2O

  • Mr = 366.45

  • Monoclinic, P 21 /n

  • a = 18.3169 (7) Å

  • b = 9.6142 (3) Å

  • c = 23.1656 (8) Å

  • β = 99.0261 (7)°

  • V = 4029.0 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 296 K

  • 0.30 × 0.30 × 0.20 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.978, Tmax = 0.985

  • 44087 measured reflections

  • 9608 independent reflections

  • 6879 reflections with I > 2σ(I)

  • Rint = 0.026
Refinement

  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.181

  • S = 1.01

  • 9608 reflections

  • 511 parameters

  • 37 restraints

  • H-atom parameters constrained

  • Δρmax = 0.60 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the N3/N4/C29–C31, C38′–C43′, C7–C12, C13–C18 and C19-C24 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C8—H8⋯Cg5i 0.93 2.87 3.585 (2) 135
C28—H28A⋯Cg2ii 0.97 2.99 3.655 (6) 127
C33—H33⋯Cg1iii 0.93 2.86 3.592 (2) 137
C37—H37⋯Cg1ii 0.93 2.96 3.789 (2) 150
C41—H41⋯Cg3iv 0.93 2.90 3.772 (10) 157
C41′—H41′⋯Cg3iv 0.93 2.85 3.705 (12) 154
C46—H46⋯Cg4 0.93 3.00 3.712 (2) 135
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) x+1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS, Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus. Bruker AXS, Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812041979/su2509sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041979/su2509Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812041979/su2509Isup3.cml

checkCIF report


Comment top

Imidazole derivatives are a great class of heterocyclic compounds due to their wide range of pharmacological and biological activities They exhibited as inhibitors of p38 MAP kinase, fungicides, herbicides, plant growth regulators, antibacterial, antitumour, pesticides and therapeutic agents (Bhatnagar et al. (2011); Puratchikody & Doble 2007; Wang et al., 2002 and Antolini, et al., 1999). They also serve as useful building blocks for synthesis of diverse class of bioactive molecules. Further to our study on synthesis of bioactive heterocyclic molecules we herein report the crystal structure of the title compound.

The molecular structure of the two independent molecules (A and B) of the title compound are illustrated in Fig. 1 Both molecules have a similar conformation. The –N—C(H2)—C(H)—C(H2) torsion angles of the prop-1-ene group are 0.5 (3) and 1.3 (4)° in molecules A and B, respectively. The bond lengths and angles of both molecules are comparable and similar to the values reported in the literature (Allen et al., 1987).

In molecule A, the central imidazole ring (N1/N2/C4–C6) forms dihedral angles of 88.26 (10), 12.74 (11) and 22.06 (9)° with the C7–C12 and C13–C18 phenyl and C19—C24 benzene rings, respectively. The corresponding angles in molecule B are 79.24 (10), 3.5 (5) [22.6 (5)] and 67.49 (10)°, with the C32–C37 and disordered C38–C43 [C38'–C43'] phenyl and C44—C49 benzene rings, respectively. In the disordered phenyl group of molecule B, the dihedral angle between the two parts is 19.1 (7)°.

In the crystal, there is no classical hydrogen bonds; the molecules are linked via C—H···π interactions (Table 1 and Fig. 2).

Related literature top

For the synthesis, see: Mohamed et al. (2012). For biological properties of imidazoles, see: Puratchikody & Doble (2007); Bhatnagar et al. (2011); Antolini et al. (1999); Wang et al. (2002). For standard 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 et al., 2012) in 88% yield. Suitable single crystals were obtained by slow evaporation of a solution in ethanol M.p. 385–387 K.

Refinement top

H atoms were positioned geometrically, C—H = 0.93 Å (aromatic), 0.96 Å (methyl) and 0.97 Å (methylene) H atoms, respectively, and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms. Each atom of the disordered phenyl ring [one part C38–C43 and the other C38'–C43'] of molecule B have an occupancy of 0.5. Their displacement parameters were restrained using ISOR. The C30—C38 and C30—C38' distances were restrained to be equal using the command SADI. Their anisotropic displacement parameters were also made equal using the EADP constraint. Two reflections, (0 2 3) and (-1 0 1), were omitted owing interference from the beam stop.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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. A view of the two independent molecules (A and B) of the title compound, with the atom numbering. Displacement ellipsoids are drawn at the 30% probability level. In molecule B only one of the disordered parts is shown.
[Figure 2] Fig. 2. A view along the b axis of the crystal packing of the title compound. H atoms have been omitted for clarity.
2-(4-Methoxyphenyl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole top
Crystal data top
C25H22N2OF(000) = 1552
Mr = 366.45Dx = 1.208 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9921 reflections
a = 18.3169 (7) Åθ = 2.3–28.8°
b = 9.6142 (3) ŵ = 0.07 mm−1
c = 23.1656 (8) ÅT = 296 K
β = 99.0261 (7)°Prism, colourless
V = 4029.0 (2) Å30.30 × 0.30 × 0.20 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer		9608 independent reflections
Radiation source: fine-focus sealed tube6879 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ϕ and ω scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −24→24
Tmin = 0.978, Tmax = 0.985k = −12→12
44087 measured reflectionsl = −30→30
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)] = 0.058Hydrogen site location: difference Fourier map
wR(F2) = 0.181H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.088P)2 + 1.3785P]
where P = (Fo2 + 2Fc2)/3
9608 reflections(Δ/σ)max < 0.001
511 parametersΔρmax = 0.60 e Å−3
37 restraintsΔρmin = −0.39 e Å−3
Crystal data top
C25H22N2OV = 4029.0 (2) Å3
Mr = 366.45Z = 8
Monoclinic, P21/nMo Kα radiation
a = 18.3169 (7) ŵ = 0.07 mm−1
b = 9.6142 (3) ÅT = 296 K
c = 23.1656 (8) Å0.30 × 0.30 × 0.20 mm
β = 99.0261 (7)°
Data collection top
Bruker APEXII CCD
diffractometer		9608 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		6879 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.985Rint = 0.026
44087 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05837 restraints
wR(F2) = 0.181H-atom parameters constrained
S = 1.01Δρmax = 0.60 e Å−3
9608 reflectionsΔρmin = −0.39 e Å−3
511 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*/UeqOcc. (<1)
O20.35130 (8)0.31803 (17)0.03555 (7)0.0694 (5)
N30.65418 (8)0.34591 (15)0.21941 (6)0.0476 (5)
N40.69985 (8)0.39192 (16)0.13852 (6)0.0494 (5)
C260.57202 (19)0.5661 (3)0.26307 (15)0.1047 (14)
C270.56204 (13)0.4411 (3)0.27676 (11)0.0761 (9)
C280.60026 (11)0.3178 (2)0.25849 (9)0.0593 (7)
C290.72817 (10)0.37696 (17)0.23660 (8)0.0447 (5)
C300.75584 (10)0.40284 (17)0.18608 (7)0.0450 (5)
C310.63998 (10)0.35807 (18)0.16008 (8)0.0471 (5)
C320.76131 (9)0.38301 (17)0.29897 (7)0.0435 (5)
C330.77225 (13)0.5095 (2)0.32740 (8)0.0603 (7)
C340.80412 (13)0.5164 (2)0.38539 (9)0.0672 (7)
C350.82503 (11)0.3971 (3)0.41585 (9)0.0623 (7)
C360.81407 (12)0.2707 (2)0.38842 (9)0.0615 (7)
C370.78263 (11)0.2638 (2)0.33034 (9)0.0533 (6)
C380.8320 (4)0.4410 (18)0.1789 (7)0.0509 (7)0.500
C38'0.8312 (5)0.4382 (18)0.1761 (7)0.0509 (7)0.500
C390.8898 (7)0.4463 (14)0.2255 (5)0.0545 (17)0.500
C39'0.8940 (7)0.4217 (15)0.2157 (5)0.0545 (17)0.500
C400.9605 (5)0.4819 (14)0.2159 (5)0.0590 (19)0.500
C40'0.9631 (6)0.4565 (14)0.2053 (5)0.0590 (19)0.500
C410.9733 (4)0.5123 (16)0.1597 (6)0.0922 (13)0.500
C41'0.9742 (5)0.5161 (18)0.1565 (7)0.0922 (13)0.500
C420.9155 (7)0.5070 (13)0.1131 (5)0.097 (3)0.500
C42'0.9129 (7)0.5598 (14)0.1165 (5)0.097 (3)0.500
C430.8448 (5)0.4713 (15)0.1227 (6)0.089 (3)0.500
C43'0.8435 (6)0.5163 (16)0.1255 (6)0.089 (3)0.500
C440.56529 (10)0.34450 (19)0.12565 (8)0.0492 (5)
C450.53132 (12)0.4605 (2)0.09929 (10)0.0683 (7)
C460.46031 (12)0.4561 (2)0.06839 (10)0.0687 (7)
C470.42230 (10)0.3326 (2)0.06372 (8)0.0525 (6)
C480.45600 (11)0.2144 (2)0.08847 (9)0.0590 (7)
C490.52640 (11)0.2200 (2)0.11945 (9)0.0567 (6)
C500.31184 (13)0.4411 (3)0.01802 (12)0.0837 (9)
O10.41271 (8)0.5961 (2)0.51655 (6)0.0853 (7)
N10.24289 (8)0.67256 (15)0.24563 (6)0.0439 (4)
N20.35708 (8)0.74733 (15)0.24549 (6)0.0467 (4)
C10.13887 (15)0.8646 (3)0.28108 (12)0.0839 (10)
C20.12641 (11)0.7324 (3)0.28092 (10)0.0685 (8)
C30.17539 (10)0.6195 (2)0.26386 (9)0.0537 (6)
C40.24870 (9)0.70292 (17)0.18810 (8)0.0449 (5)
C50.32016 (9)0.74795 (18)0.18908 (8)0.0447 (5)
C60.30977 (9)0.70180 (17)0.27875 (7)0.0434 (5)
C70.18709 (9)0.67909 (18)0.13956 (8)0.0460 (5)
C80.13833 (11)0.7848 (2)0.11944 (10)0.0652 (7)
C90.08342 (13)0.7631 (3)0.07206 (12)0.0778 (9)
C100.07678 (13)0.6373 (3)0.04448 (10)0.0733 (8)
C110.12369 (14)0.5311 (3)0.06443 (10)0.0734 (8)
C120.17867 (12)0.5519 (2)0.11174 (9)0.0597 (6)
C130.35943 (10)0.78571 (19)0.14044 (8)0.0496 (6)
C140.32434 (15)0.8064 (3)0.08369 (10)0.0784 (9)
C150.3645 (2)0.8332 (3)0.03948 (12)0.0982 (13)
C160.43927 (19)0.8436 (3)0.05000 (13)0.0902 (13)
C170.47490 (15)0.8273 (3)0.10583 (13)0.0791 (10)
C180.43551 (12)0.7975 (2)0.15076 (10)0.0626 (7)
C190.33115 (9)0.67911 (18)0.34176 (8)0.0448 (5)
C200.40664 (10)0.6643 (2)0.36323 (8)0.0537 (6)
C210.43180 (10)0.6392 (2)0.42109 (9)0.0593 (6)
C220.38231 (11)0.6259 (2)0.46035 (8)0.0576 (6)
C230.30776 (10)0.6440 (2)0.44088 (8)0.0579 (7)
C240.28301 (10)0.6711 (2)0.38261 (8)0.0525 (6)
C250.36398 (18)0.5660 (5)0.55645 (12)0.1319 (18)
H26A0.606600.587500.239000.1260*
H26B0.544800.636700.277100.1260*
H270.526900.425300.300900.0910*
H28A0.625500.271600.293200.0710*
H28B0.563400.253900.239000.0710*
H330.757900.591100.307200.0720*
H340.811400.602300.403800.0810*
H350.846600.401800.454900.0750*
H360.827900.189500.409000.0740*
H370.775700.177600.312100.0640*
H390.881300.426000.263100.0650*0.500
H39'0.889500.384500.252000.0650*0.500
H400.999200.485500.247100.0710*0.500
H40'1.003600.437200.233800.0710*0.500
H411.020600.536100.153200.1100*0.500
H41'1.021900.529200.148600.1100*0.500
H420.924000.527300.075400.1160*0.500
H42'0.918700.616100.084900.1160*0.500
H430.806100.467800.091500.1070*0.500
H43'0.802900.538600.097600.1070*0.500
H450.556800.544500.102300.0820*
H460.438500.536200.050900.0820*
H480.431000.129900.084200.0710*
H490.548200.139500.136500.0680*
H50A0.263100.41760−0.001300.1250*
H50B0.337300.49220−0.008300.1250*
H50C0.308200.497100.051800.1250*
H1A0.182100.898300.269800.1010*
H1B0.104700.926100.292500.1010*
H20.082400.704200.292600.0820*
H3A0.188600.557200.296800.0640*
H3B0.148100.566000.232100.0640*
H80.142500.871000.137900.0780*
H90.050800.834600.058900.0930*
H100.040400.623800.012100.0880*
H110.118600.444800.046100.0880*
H120.210400.479200.125000.0720*
H140.273000.802100.075300.0940*
H150.339900.844400.001500.1180*
H160.465700.861500.019700.1080*
H170.526000.836200.113800.0950*
H180.460700.785200.188500.0750*
H200.440600.671700.337400.0640*
H210.482300.631000.434100.0710*
H230.274200.637900.467000.0690*
H240.232700.684500.370200.0630*
H25A0.392000.548000.594300.1980*
H25B0.335000.485700.543300.1980*
H25C0.331900.644100.558800.1980*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0490 (8)0.0850 (11)0.0688 (9)−0.0031 (7)−0.0075 (7)−0.0143 (8)
N30.0471 (8)0.0474 (8)0.0463 (8)−0.0054 (6)0.0015 (6)−0.0007 (6)
N40.0473 (8)0.0524 (8)0.0464 (8)0.0008 (6)0.0007 (6)−0.0031 (6)
C260.114 (2)0.085 (2)0.127 (3)0.0191 (17)0.056 (2)0.0053 (18)
C270.0659 (14)0.0991 (19)0.0663 (14)0.0022 (13)0.0199 (11)−0.0006 (13)
C280.0536 (11)0.0711 (13)0.0527 (11)−0.0136 (9)0.0070 (8)0.0046 (9)
C290.0467 (9)0.0371 (8)0.0481 (9)−0.0014 (7)0.0010 (7)−0.0012 (7)
C300.0464 (9)0.0415 (8)0.0452 (9)0.0026 (7)0.0009 (7)−0.0020 (7)
C310.0476 (9)0.0447 (9)0.0471 (9)−0.0002 (7)0.0018 (7)−0.0038 (7)
C320.0437 (8)0.0422 (8)0.0433 (8)−0.0041 (7)0.0029 (7)0.0030 (7)
C330.0883 (15)0.0410 (9)0.0477 (10)−0.0088 (9)−0.0010 (10)0.0042 (8)
C340.0916 (16)0.0606 (12)0.0475 (10)−0.0196 (11)0.0047 (10)−0.0042 (9)
C350.0567 (11)0.0866 (15)0.0419 (9)−0.0046 (10)0.0024 (8)0.0066 (10)
C360.0623 (12)0.0677 (13)0.0545 (11)0.0161 (10)0.0088 (9)0.0204 (10)
C370.0601 (11)0.0434 (9)0.0565 (11)0.0055 (8)0.0096 (9)0.0045 (8)
C380.0468 (9)0.0560 (11)0.0495 (14)0.0054 (8)0.0060 (8)−0.0034 (10)
C38'0.0468 (9)0.0560 (11)0.0495 (14)0.0054 (8)0.0060 (8)−0.0034 (10)
C390.0537 (16)0.059 (4)0.050 (3)−0.005 (2)0.0055 (17)0.002 (3)
C39'0.0537 (16)0.059 (4)0.050 (3)−0.005 (2)0.0055 (17)0.002 (3)
C400.0494 (12)0.062 (4)0.063 (4)−0.0012 (17)0.0008 (17)−0.002 (3)
C40'0.0494 (12)0.062 (4)0.063 (4)−0.0012 (17)0.0008 (17)−0.002 (3)
C410.0475 (12)0.155 (3)0.076 (2)−0.0038 (15)0.0157 (11)−0.0006 (18)
C41'0.0475 (12)0.155 (3)0.076 (2)−0.0038 (15)0.0157 (11)−0.0006 (18)
C420.0684 (17)0.164 (9)0.0612 (18)−0.014 (4)0.0200 (14)0.000 (4)
C42'0.0684 (17)0.164 (9)0.0612 (18)−0.014 (4)0.0200 (14)0.000 (4)
C430.0554 (13)0.160 (8)0.0508 (16)−0.010 (3)0.0063 (11)−0.004 (4)
C43'0.0554 (13)0.160 (8)0.0508 (16)−0.010 (3)0.0063 (11)−0.004 (4)
C440.0468 (9)0.0524 (10)0.0463 (9)−0.0024 (8)0.0007 (7)−0.0043 (8)
C450.0620 (12)0.0536 (11)0.0813 (15)−0.0116 (9)−0.0135 (11)0.0102 (10)
C460.0626 (12)0.0589 (12)0.0763 (14)−0.0019 (10)−0.0146 (11)0.0088 (11)
C470.0454 (9)0.0670 (12)0.0437 (9)−0.0036 (8)0.0027 (7)−0.0118 (8)
C480.0563 (11)0.0535 (11)0.0649 (12)−0.0104 (9)0.0028 (9)−0.0119 (9)
C490.0562 (11)0.0491 (10)0.0623 (12)−0.0007 (8)0.0012 (9)−0.0047 (9)
C500.0544 (12)0.106 (2)0.0837 (16)0.0134 (13)−0.0106 (11)−0.0220 (15)
O10.0573 (9)0.1517 (17)0.0435 (8)0.0046 (10)−0.0027 (6)0.0062 (9)
N10.0393 (7)0.0465 (8)0.0453 (7)0.0014 (6)0.0050 (6)0.0036 (6)
N20.0417 (7)0.0500 (8)0.0476 (8)0.0008 (6)0.0049 (6)0.0033 (6)
C10.0707 (15)0.0872 (19)0.0921 (18)0.0264 (13)0.0075 (13)−0.0095 (14)
C20.0370 (9)0.1041 (19)0.0649 (13)0.0000 (10)0.0093 (9)−0.0013 (12)
C30.0464 (9)0.0589 (11)0.0550 (10)−0.0126 (8)0.0059 (8)0.0041 (8)
C40.0457 (9)0.0420 (8)0.0457 (9)0.0041 (7)0.0034 (7)0.0030 (7)
C50.0433 (8)0.0430 (9)0.0469 (9)0.0016 (7)0.0043 (7)0.0036 (7)
C60.0388 (8)0.0429 (8)0.0477 (9)0.0022 (7)0.0048 (7)0.0016 (7)
C70.0421 (9)0.0488 (9)0.0460 (9)−0.0007 (7)0.0032 (7)0.0041 (7)
C80.0590 (12)0.0499 (11)0.0785 (14)0.0038 (9)−0.0151 (10)−0.0015 (10)
C90.0599 (13)0.0715 (15)0.0908 (17)0.0033 (11)−0.0231 (12)0.0118 (13)
C100.0615 (13)0.0886 (17)0.0625 (13)−0.0146 (12)−0.0126 (10)0.0015 (12)
C110.0801 (15)0.0712 (14)0.0647 (13)−0.0081 (12)−0.0017 (11)−0.0190 (11)
C120.0610 (11)0.0561 (11)0.0600 (11)0.0058 (9)0.0029 (9)−0.0050 (9)
C130.0543 (10)0.0437 (9)0.0515 (10)0.0005 (8)0.0109 (8)0.0048 (7)
C140.0766 (15)0.0973 (18)0.0597 (13)−0.0072 (13)0.0057 (11)0.0277 (12)
C150.126 (3)0.111 (2)0.0597 (14)−0.0142 (19)0.0208 (15)0.0292 (14)
C160.126 (3)0.0722 (16)0.0857 (19)−0.0062 (16)0.0581 (18)0.0139 (13)
C170.0759 (15)0.0681 (14)0.103 (2)−0.0029 (12)0.0446 (15)0.0042 (13)
C180.0592 (12)0.0637 (12)0.0671 (13)−0.0022 (10)0.0172 (10)0.0035 (10)
C190.0405 (8)0.0456 (9)0.0471 (9)0.0012 (7)0.0028 (7)−0.0003 (7)
C200.0401 (9)0.0699 (12)0.0514 (10)−0.0025 (8)0.0082 (7)−0.0012 (9)
C210.0375 (9)0.0860 (14)0.0516 (10)−0.0002 (9)−0.0019 (8)−0.0033 (10)
C220.0491 (10)0.0773 (13)0.0437 (9)0.0007 (9)−0.0009 (8)−0.0021 (9)
C230.0454 (10)0.0815 (14)0.0470 (10)0.0019 (9)0.0081 (8)0.0015 (9)
C240.0366 (8)0.0694 (12)0.0500 (10)0.0045 (8)0.0022 (7)0.0023 (9)
C250.0859 (19)0.259 (5)0.0510 (14)0.016 (3)0.0110 (13)0.032 (2)
Geometric parameters (Å, º) top
O2—C471.368 (2)C41—H410.9300
O2—C501.413 (3)C41'—H41'0.9300
O1—C221.364 (2)C42—H420.9300
O1—C251.412 (3)C42'—H42'0.9300
N3—C311.363 (2)C43—H430.9300
N3—C291.384 (2)C43'—H43'0.9300
N3—C281.466 (3)C45—H450.9300
N4—C301.386 (2)C46—H460.9300
N4—C311.315 (2)C48—H480.9300
N1—C41.385 (2)C49—H490.9300
N1—C61.369 (2)C50—H50A0.9600
N1—C31.460 (2)C50—H50B0.9600
N2—C51.374 (2)C50—H50C0.9600
N2—C61.321 (2)C1—C21.291 (4)
C26—C271.264 (4)C2—C31.500 (3)
C27—C281.472 (3)C4—C51.376 (2)
C29—C301.369 (2)C4—C71.481 (2)
C29—C321.478 (2)C5—C131.474 (3)
C30—C381.477 (9)C6—C191.467 (2)
C30—C38'1.475 (10)C7—C81.385 (3)
C31—C441.477 (3)C7—C121.380 (3)
C32—C331.383 (3)C8—C91.383 (3)
C32—C371.380 (3)C9—C101.364 (4)
C33—C341.380 (3)C10—C111.367 (4)
C34—C351.369 (3)C11—C121.382 (3)
C35—C361.371 (3)C13—C141.384 (3)
C36—C371.380 (3)C13—C181.381 (3)
C38—C431.39 (2)C14—C151.376 (4)
C38—C391.389 (18)C15—C161.357 (5)
C38'—C39'1.363 (18)C16—C171.363 (4)
C38'—C43'1.44 (2)C17—C181.386 (4)
C39—C401.391 (16)C19—C201.401 (3)
C39'—C40'1.367 (17)C19—C241.393 (3)
C40—C411.390 (18)C20—C211.369 (3)
C40'—C41'1.31 (2)C21—C221.387 (3)
C41—C421.389 (17)C22—C231.380 (3)
C41'—C42'1.403 (18)C23—C241.380 (3)
C42—C431.391 (16)C1—H1A0.9300
C42'—C43'1.385 (17)C1—H1B0.9300
C44—C451.373 (3)C2—H20.9300
C44—C491.389 (3)C3—H3A0.9700
C45—C461.383 (3)C3—H3B0.9700
C46—C471.372 (3)C8—H80.9300
C47—C481.375 (3)C9—H90.9300
C48—C491.375 (3)C10—H100.9300
C26—H26B0.9300C11—H110.9300
C26—H26A0.9300C12—H120.9300
C27—H270.9300C14—H140.9300
C28—H28B0.9700C15—H150.9300
C28—H28A0.9700C16—H160.9300
C33—H330.9300C17—H170.9300
C34—H340.9300C18—H180.9300
C35—H350.9300C20—H200.9300
C36—H360.9300C21—H210.9300
C37—H370.9300C23—H230.9300
C39—H390.9300C24—H240.9300
C39'—H39'0.9300C25—H25A0.9600
C40—H400.9300C25—H25B0.9600
C40'—H40'0.9300C25—H25C0.9600
C47—O2—C50117.18 (17)C42'—C43'—H43'119.00
C22—O1—C25117.56 (18)C44—C45—H45119.00
C28—N3—C29125.90 (15)C46—C45—H45119.00
C28—N3—C31126.73 (15)C47—C46—H46120.00
C29—N3—C31107.16 (15)C45—C46—H46120.00
C30—N4—C31105.89 (14)C49—C48—H48120.00
C3—N1—C6129.33 (15)C47—C48—H48120.00
C3—N1—C4123.27 (15)C44—C49—H49120.00
C4—N1—C6107.40 (14)C48—C49—H49120.00
C5—N2—C6106.62 (14)H50A—C50—H50C109.00
C26—C27—C28126.9 (3)H50B—C50—H50C109.00
N3—C28—C27115.21 (17)O2—C50—H50A109.00
N3—C29—C30105.69 (15)O2—C50—H50B110.00
N3—C29—C32121.55 (15)O2—C50—H50C109.00
C30—C29—C32132.70 (17)H50A—C50—H50B109.00
N4—C30—C38121.6 (6)C1—C2—C3126.9 (2)
N4—C30—C38'119.1 (6)N1—C3—C2113.08 (17)
N4—C30—C29109.79 (16)N1—C4—C5105.49 (15)
C38—C30—C38'2.7 (9)N1—C4—C7122.27 (15)
C29—C30—C38128.6 (6)C5—C4—C7132.16 (17)
C29—C30—C38'131.1 (6)N2—C5—C4109.84 (16)
N4—C31—C44125.00 (16)N2—C5—C13120.11 (15)
N3—C31—C44123.42 (16)C4—C5—C13129.95 (17)
N3—C31—N4111.44 (16)N1—C6—N2110.63 (14)
C29—C32—C37121.39 (15)N1—C6—C19127.08 (15)
C33—C32—C37118.14 (16)N2—C6—C19122.17 (15)
C29—C32—C33120.46 (15)C4—C7—C8121.10 (16)
C32—C33—C34120.91 (17)C4—C7—C12120.53 (16)
C33—C34—C35120.19 (19)C8—C7—C12118.32 (18)
C34—C35—C36119.65 (19)C7—C8—C9120.4 (2)
C35—C36—C37120.19 (19)C8—C9—C10120.4 (2)
C32—C37—C36120.92 (18)C9—C10—C11119.9 (2)
C30—C38—C43117.3 (10)C10—C11—C12120.1 (2)
C30—C38—C39122.7 (12)C7—C12—C11120.9 (2)
C39—C38—C43120.0 (9)C5—C13—C14123.49 (19)
C30—C38'—C39'125.4 (13)C5—C13—C18119.21 (17)
C30—C38'—C43'121.2 (10)C14—C13—C18117.3 (2)
C39'—C38'—C43'112.7 (10)C13—C14—C15120.7 (3)
C38—C39—C40120.0 (11)C14—C15—C16121.5 (3)
C38'—C39'—C40'124.1 (12)C15—C16—C17118.8 (3)
C39—C40—C41120.0 (10)C16—C17—C18120.5 (3)
C39'—C40'—C41'122.2 (11)C13—C18—C17121.1 (2)
C40—C41—C42120.0 (9)C6—C19—C20117.57 (15)
C40'—C41'—C42'118.9 (10)C6—C19—C24125.84 (16)
C41—C42—C43120.0 (11)C20—C19—C24116.60 (17)
C41'—C42'—C43'117.9 (12)C19—C20—C21121.83 (17)
C38—C43—C42120.0 (11)C20—C21—C22120.27 (18)
C38'—C43'—C42'123.0 (11)O1—C22—C21115.75 (18)
C31—C44—C45119.02 (17)O1—C22—C23124.98 (17)
C45—C44—C49117.70 (18)C21—C22—C23119.27 (17)
C31—C44—C49123.26 (17)C22—C23—C24119.99 (17)
C44—C45—C46121.94 (18)C19—C24—C23121.95 (17)
C45—C46—C47119.44 (18)C2—C1—H1A120.00
C46—C47—C48119.56 (18)C2—C1—H1B120.00
O2—C47—C46123.99 (18)H1A—C1—H1B120.00
O2—C47—C48116.45 (17)C1—C2—H2117.00
C47—C48—C49120.55 (18)C3—C2—H2117.00
C44—C49—C48120.77 (18)N1—C3—H3A109.00
C27—C26—H26A120.00N1—C3—H3B109.00
H26A—C26—H26B120.00C2—C3—H3A109.00
C27—C26—H26B120.00C2—C3—H3B109.00
C26—C27—H27117.00H3A—C3—H3B108.00
C28—C27—H27117.00C7—C8—H8120.00
N3—C28—H28B108.00C9—C8—H8120.00
C27—C28—H28A108.00C8—C9—H9120.00
N3—C28—H28A108.00C10—C9—H9120.00
C27—C28—H28B108.00C9—C10—H10120.00
H28A—C28—H28B108.00C11—C10—H10120.00
C32—C33—H33120.00C10—C11—H11120.00
C34—C33—H33119.00C12—C11—H11120.00
C33—C34—H34120.00C7—C12—H12120.00
C35—C34—H34120.00C11—C12—H12120.00
C36—C35—H35120.00C13—C14—H14120.00
C34—C35—H35120.00C15—C14—H14120.00
C37—C36—H36120.00C14—C15—H15119.00
C35—C36—H36120.00C16—C15—H15119.00
C32—C37—H37120.00C15—C16—H16121.00
C36—C37—H37119.00C17—C16—H16121.00
C40—C39—H39120.00C16—C17—H17120.00
C38—C39—H39120.00C18—C17—H17120.00
C38'—C39'—H39'118.00C13—C18—H18119.00
C40'—C39'—H39'118.00C17—C18—H18119.00
C41—C40—H40120.00C19—C20—H20119.00
C39—C40—H40120.00C21—C20—H20119.00
C41'—C40'—H40'119.00C20—C21—H21120.00
C39'—C40'—H40'119.00C22—C21—H21120.00
C40—C41—H41120.00C22—C23—H23120.00
C42—C41—H41120.00C24—C23—H23120.00
C42'—C41'—H41'121.00C19—C24—H24119.00
C40'—C41'—H41'120.00C23—C24—H24119.00
C43—C42—H42120.00O1—C25—H25A109.00
C41—C42—H42120.00O1—C25—H25B109.00
C41'—C42'—H42'121.00O1—C25—H25C109.00
C43'—C42'—H42'121.00H25A—C25—H25B110.00
C42—C43—H43120.00H25A—C25—H25C109.00
C38—C43—H43120.00H25B—C25—H25C110.00
C38'—C43'—H43'118.00
C50—O2—C47—C46−9.7 (3)C39—C38—C43—C420 (2)
C50—O2—C47—C48170.20 (19)C30—C38'—C39'—C40'−179.5 (13)
C25—O1—C22—C237.5 (4)C43'—C38'—C39'—C40'−9 (2)
C25—O1—C22—C21−172.9 (3)C30—C38'—C43'—C42'175.5 (12)
C31—N3—C28—C27−85.4 (2)C39'—C38'—C43'—C42'5 (2)
C29—N3—C28—C2788.6 (2)C38—C39—C40—C410 (2)
C31—N3—C29—C30−1.67 (18)C38'—C39'—C40'—C41'4 (2)
C31—N3—C29—C32175.86 (15)C39—C40—C41—C420 (2)
C28—N3—C31—N4176.12 (16)C39'—C40'—C41'—C42'7 (2)
C28—N3—C31—C440.2 (3)C40—C41—C42—C430 (2)
C29—N3—C31—N41.2 (2)C40'—C41'—C42'—C43'−11 (2)
C28—N3—C29—C30−176.65 (16)C41—C42—C43—C380 (2)
C28—N3—C29—C320.9 (3)C41'—C42'—C43'—C38'5 (2)
C29—N3—C31—C44−174.72 (16)C49—C44—C45—C461.2 (3)
C31—N4—C30—C38'179.2 (8)C31—C44—C49—C48177.81 (18)
C30—N4—C31—N3−0.2 (2)C31—C44—C45—C46−177.4 (2)
C30—N4—C31—C44175.64 (16)C45—C44—C49—C48−0.7 (3)
C31—N4—C30—C38−179.5 (8)C44—C45—C46—C470.0 (3)
C31—N4—C30—C29−0.90 (19)C45—C46—C47—O2178.17 (19)
C6—N1—C4—C50.80 (18)C45—C46—C47—C48−1.7 (3)
C3—N1—C6—C193.6 (3)C46—C47—C48—C492.2 (3)
C6—N1—C4—C7177.86 (15)O2—C47—C48—C49−177.69 (18)
C3—N1—C6—N2179.59 (16)C47—C48—C49—C44−1.0 (3)
C4—N1—C3—C2−91.9 (2)C1—C2—C3—N1−0.5 (3)
C6—N1—C3—C288.0 (2)N1—C4—C5—N2−0.81 (19)
C3—N1—C4—C5−179.30 (15)N1—C4—C5—C13175.52 (17)
C3—N1—C4—C7−2.2 (2)C7—C4—C5—N2−177.45 (17)
C4—N1—C6—N2−0.53 (19)C7—C4—C5—C13−1.1 (3)
C4—N1—C6—C19−176.52 (16)N1—C4—C7—C894.8 (2)
C6—N2—C5—C40.50 (19)N1—C4—C7—C12−87.8 (2)
C5—N2—C6—C19176.24 (15)C5—C4—C7—C8−89.1 (3)
C6—N2—C5—C13−176.24 (16)C5—C4—C7—C1288.4 (3)
C5—N2—C6—N10.02 (18)N2—C5—C13—C14−171.3 (2)
C26—C27—C28—N3−1.3 (4)N2—C5—C13—C1810.8 (3)
C30—C29—C32—C37−102.5 (2)C4—C5—C13—C1412.7 (3)
N3—C29—C30—N41.60 (19)C4—C5—C13—C18−165.25 (19)
N3—C29—C30—C38−180.0 (9)N1—C6—C19—C20155.90 (17)
N3—C29—C30—C38'−178.5 (9)N1—C6—C19—C24−24.2 (3)
C32—C29—C30—N4−175.53 (17)N2—C6—C19—C20−19.7 (2)
C32—C29—C30—C382.9 (9)N2—C6—C19—C24160.20 (18)
C32—C29—C30—C38'4.4 (9)C4—C7—C8—C9176.6 (2)
N3—C29—C32—C33−99.7 (2)C12—C7—C8—C9−1.0 (3)
N3—C29—C32—C3780.8 (2)C4—C7—C12—C11−176.56 (19)
C30—C29—C32—C3377.1 (3)C8—C7—C12—C111.0 (3)
N4—C30—C38—C432.6 (17)C7—C8—C9—C10−0.2 (4)
C29—C30—C38—C394.8 (19)C8—C9—C10—C111.3 (4)
C29—C30—C38—C43−175.6 (9)C9—C10—C11—C12−1.3 (4)
N4—C30—C38'—C39'−164.1 (12)C10—C11—C12—C70.1 (4)
N4—C30—C38'—C43'26.4 (17)C5—C13—C14—C15−176.0 (2)
C29—C30—C38'—C39'16 (2)C18—C13—C14—C152.0 (4)
C29—C30—C38'—C43'−153.5 (10)C5—C13—C18—C17177.4 (2)
N4—C30—C38—C39−176.9 (11)C14—C13—C18—C17−0.7 (3)
N3—C31—C44—C49−68.3 (3)C13—C14—C15—C16−1.6 (4)
N4—C31—C44—C45−65.1 (3)C14—C15—C16—C17−0.2 (4)
N4—C31—C44—C49116.4 (2)C15—C16—C17—C181.5 (4)
N3—C31—C44—C45110.2 (2)C16—C17—C18—C13−1.0 (4)
C37—C32—C33—C340.5 (3)C6—C19—C20—C21−178.27 (17)
C29—C32—C37—C36179.46 (18)C24—C19—C20—C211.8 (3)
C29—C32—C33—C34−179.1 (2)C6—C19—C24—C23177.41 (18)
C33—C32—C37—C36−0.1 (3)C20—C19—C24—C23−2.7 (3)
C32—C33—C34—C35−0.4 (4)C19—C20—C21—C220.8 (3)
C33—C34—C35—C36−0.1 (3)C20—C21—C22—O1177.75 (18)
C34—C35—C36—C370.5 (3)C20—C21—C22—C23−2.7 (3)
C35—C36—C37—C32−0.4 (3)O1—C22—C23—C24−178.66 (19)
C30—C38—C39—C40179.5 (12)C21—C22—C23—C241.8 (3)
C43—C38—C39—C400 (2)C22—C23—C24—C190.9 (3)
C30—C38—C43—C42−179.6 (12)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the N3/N4/C29–C31, C38'–C43', C7–C12, C13–C18 and C19-C24 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C8—H8···Cg5i0.932.873.585 (2)135
C28—H28A···Cg2ii0.972.993.655 (6)127
C33—H33···Cg1iii0.932.863.592 (2)137
C37—H37···Cg1ii0.932.963.789 (2)150
C41—H41···Cg3iv0.932.903.772 (10)157
C41′—H41′···Cg3iv0.932.853.705 (12)154
C46—H46···Cg40.933.003.712 (2)135
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC25H22N2O
Mr366.45
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)18.3169 (7), 9.6142 (3), 23.1656 (8)
β (°) 99.0261 (7)
V (Å3)4029.0 (2)
Z8
Radiation typeMo Kα
µ (mm−1)0.07
Crystal size (mm)0.30 × 0.30 × 0.20
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.978, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections		44087, 9608, 6879
Rint0.026
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.181, 1.01
No. of reflections9608
No. of parameters511
No. of restraints37
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.60, −0.39

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), 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
Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the N3/N4/C29–C31, C38'–C43', C7–C12, C13–C18 and C19-C24 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C8—H8···Cg5i0.932.873.585 (2)135
C28—H28A···Cg2ii0.972.993.655 (6)127
C33—H33···Cg1iii0.932.863.592 (2)137
C37—H37···Cg1ii0.932.963.789 (2)150
C41—H41···Cg3iv0.932.903.772 (10)157
C41'—H41'···Cg3iv0.932.853.705 (12)154
C46—H46···Cg40.933.003.712 (2)135
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2; (iv) x+1, y, z.
 

Acknowledgements

The National Academy of Sciences of Azerbaijan, Erciyes University and Baku state University are gratefully acknowledged for supporting this study.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
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 First citationPuratchikody, A. & Doble, M. (2007). Bioorg. Med. Chem. Lett. 15, 1083–1090.  CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.  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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ISSN: 2056-9890
Volume 68| Part 11| November 2012| Pages o3113-o3114
doi:10.1107/S1600536812041979
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