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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 7| July 2013| Pages o1105-o1106

Prop-2-en-1-yl 4-(4,5-di­phenyl-1H-imidazol-2-yl)benzoate

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, dPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt, eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada, E-18071, Spain
*Correspondence e-mail: shaabankamel@yahoo.com

(Received 10 June 2013; accepted 11 June 2013; online 15 June 2013)

The title compound, C25H20N2O2, crystallized with two mol­ecules in the asymmetric unit, in one of which the atoms of the terminal propenyl group are disordered over two sets of sites, with a refined occupancy ratio of 0.870 (4):0.130 (4). The central imidazole ring makes dihedral angles of 25.51 (11), 40.73 (11) and 27.36 (11)° with the three pendant rings in one molecule and 22.56 (10), 60.72 (10) and 5.85 (10)° in the other. In the crystal, mol­ecules are linked by N—H⋯N and C—H⋯O hydrogen bonds, forming a three-dimensional network. The crystal structure also features C—H⋯π inter­actions and ππ stacking [centroid–centroid distances = 3.8834 (18) and 3.9621 (17) Å] inter­actions.

Related literature

For the synthesis and biological activity of imidazole compounds, see, for example: Bhatnagar et al. (2011[Bhatnagar, A., Sharma, P. K. & Kumar, N. (2011). Int. J. PharmTech Res. 3, 268-282.]); Sisko & Mellinger (2002[Sisko, J. & Mellinger, M. (2002). Pure Appl. Chem. 74, 1349-1357.]). For similar structures, see: Akkurt et al. (2013a[Akkurt, M., Fronczek, F. R., Mohamed, S. K., Talybov, A. H., Marzouk, A. A. E. & Abdelhamid, A. A. (2013a). Acta Cryst. E69, o527-o528.],b[Akkurt, M., Mohamed, S. K., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013b). Acta Cryst. E69, o846-o847.]); Mohamed et al. (2013a[Mohamed, S. K., Akkurt, M., Marzouk, A. A., Abbasov, V. M. & Gurbanov, A. V. (2013a). Acta Cryst. E69, o474-o475.],b[Mohamed, S. K., Akkurt, M., Marzouk, A. A. E., Santoyo-Gonzalez, F. & Elremaily, M. A. A. (2013b). Acta Cryst. E69, o875-o876.]).

[Scheme 1]

Experimental

Crystal data
  • C25H20N2O2

  • Mr = 380.43

  • Monoclinic, P 21 /c

  • a = 15.705 (5) Å

  • b = 14.888 (5) Å

  • c = 17.589 (6) Å

  • β = 105.151 (4)°

  • V = 3970 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.73 × 0.35 × 0.15 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.988

  • 46196 measured reflections

  • 9345 independent reflections

  • 6507 reflections with I > 2σ(I)

  • Rint = 0.064

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.149

  • S = 1.02

  • 9345 reflections

  • 530 parameters

  • 42 restraints

  • H-atom parameters constrained

  • Δρmax = 0.51 e Å−3

  • Δρmin = −0.47 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1/N2/C1–C3 1H-imidazole ring and the C4–C9 and C10–C15 phenyl rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯N4i 0.90 (2) 2.14 (2) 3.037 (2) 176 (2)
N3—H3N⋯N2 0.89 (2) 2.06 (2) 2.925 (2) 164 (2)
C7—H7⋯O1ii 0.95 2.45 3.254 (3) 142
C32—H32⋯O3iii 0.95 2.51 3.439 (3) 167
C23—H23ACg1iv 0.99 2.74 3.524 (3) 136
C25A—H25BCg2v 0.95 2.79 3.687 (3) 158
C37—H37⋯Cg3vi 0.95 2.90 3.634 (3) 134
C25B—H25DCg2v 0.95 2.68 3.44 (2) 137
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x, y-1, z; (iii) x-1, y, z; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (v) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (vi) -x, -y, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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

Imidazole compounds represent a wide range of bio-activities such as anti-fungal, anti-inflammatory, anti-anthelmintic, anti-viral and anti-ulcer activities in addition to their use in treatment of rheumatoid arthritis (Bhatnagar et al., 2011; Sisko & Mellinger, 2002). Based on such facts and following to our ongoing study on synthesis of unsaturated substituted imidazoles as a convenient substrate to design bioactive molecules, we herein report the synthesis and crystal structure of the title compound.

Fig. 1 shows the two molecules A (with N1) and B (with N3) of the title compound (I), in the asymmetric unit. In molecule A, the 1H-imidazole ring (N1/N2/C1–C3) makes dihedral angles of 25.51 (11), 40.73 (11) and 27.36 (11)°, respectively, with the two phenyl rings (C4–C9 and C10–C15) and the benzene ring (C16–C21). In molecule B, due to the different molecular environment in the crystal, the corresponding angles are different, viz. 22.56 (10), 60.72 (10) and 5.85 (10)°, respectively. In molecule A, the phenyl rings (C4–C9 and C10–C15) form dihedral angles of 21.36 (10) and 26.58 (10) °, respectively with the benzene ring (C16–C21), while the dihedral angle between them is 47.42 (10)°. In molecule B, the corresponding angles are different, viz.16.94 (10), 60.11 (9) and 65.48 (10)°. The bond lengths in (I) are normal and are comparable to those reported for similar compounds (Akkurt et al., 2013a,b; Mohamed et al., 2013a,b).

Intermolecular N—H···N and C—H···O hydrogen bonds link the adjacent molecules, into a three dimensional network structure (Table 1, Fig. 2). C—H···π interactions (Table 1) and π-π stacking interactions [Cg1···Cg7(x, y, z) = 3.8834 (18) Å and Cg8···Cg8(1 - x, -y, 2 - z) = 3.9621 (17) Å; where Cg1 is the centroid of the 1H-imidazole ring (N1/N2/C1–C3) of molecule A; Cg7 and Cg8 are the centroids of the phenyl (C35–C40) and benzene (C41–C46) rings of molecule B] are significant contributors in the stabilization of the crystal packing of (I).

Related literature top

For the synthesis and biological activity of imidazole compounds, see, for example: Bhatnagar et al. (2011); Sisko & Mellinger (2002). For similar structures, see: Akkurt et al. (2013a,b); Mohamed et al. (2013a,b).

Experimental top

A solution of 10 mmol (570 mg) potassium hydroxide in 25 ml dimethyl sulfoxide was charged in a 50-ml volumetric flask equipped with a magnetic stirring bar. The mixture was stirred at room temperature for 5 minutes followed by addition of 10 mmol (3.40 g) 4-(4,5-diphenyl-1H-imidazol-2-yl)benzoic acid with stirring for further 30 minutes. A solution of 10 mmol (1.21 g) allyl bromide was added dropwise with stirring for additional 45 minutes. The reaction mixture was diluted with 20 ml water. The mixture was extracted with 3x20 ml diethyl ether. The combined ether layers were dried over calcium chloride. The excess solvent was removed under slightly reduced pressure and the excess allyl bromide was removed by distillation at approximately 15 mm. The raw product was collected and crystallized from ethanol to give the title compound. Single crystals suitable for X-ray diffractions were grown up by slow evaporation of an ethanol solution for the title compound at room temperature.

Refinement top

The H atoms attached to the C atoms were placed in geometrically, with C—H = 0.95–0.99 Å, and refined as riding with Uiso(H) = 1.2Ueq(C). The H atoms of the two amide groups were located from a difference Fourier map and refined with riding model constraints and Uiso(H) = 1.2Ueq(N). The atoms of the terminal propenyl group are disordered over two sites with refined occupancies of 0.870 (4) and 0.130 (4).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR97 (Altomare et al., 1999); 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. The molecular structure of (I) with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Only the major components of disorder are shown.
[Figure 2] Fig. 2. A part of the hydrogen bonding and packing of (I) viewing along the [-110]-axis. H atoms not involved in hydrogen bonds and the minor components of disorder have been omitted for clarity.
Prop-2-en-1-yl 4-(4,5-diphenyl-1H-imidazol-2-yl)benzoate top
Crystal data top
C25H20N2O2F(000) = 1600
Mr = 380.43Dx = 1.273 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5599 reflections
a = 15.705 (5) Åθ = 2.4–24.2°
b = 14.888 (5) ŵ = 0.08 mm1
c = 17.589 (6) ÅT = 100 K
β = 105.151 (4)°Prism, colourless
V = 3970 (2) Å30.73 × 0.35 × 0.15 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
9345 independent reflections
Radiation source: sealed tube6507 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
phi and ω scansθmax = 28.1°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 2019
Tmin = 0.967, Tmax = 0.988k = 1919
46196 measured reflectionsl = 2323
Refinement top
Refinement on F242 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.149 W = 1/[Σ2(FO2) + (0.0551P)2 + 2.4694P]
where P = (FO2 + 2FC2)/3
S = 1.02(Δ/σ)max < 0.001
9345 reflectionsΔρmax = 0.51 e Å3
530 parametersΔρmin = 0.47 e Å3
Crystal data top
C25H20N2O2V = 3970 (2) Å3
Mr = 380.43Z = 8
Monoclinic, P21/cMo Kα radiation
a = 15.705 (5) ŵ = 0.08 mm1
b = 14.888 (5) ÅT = 100 K
c = 17.589 (6) Å0.73 × 0.35 × 0.15 mm
β = 105.151 (4)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
9345 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
6507 reflections with I > 2σ(I)
Tmin = 0.967, Tmax = 0.988Rint = 0.064
46196 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05842 restraints
wR(F2) = 0.149H-atom parameters constrained
S = 1.02Δρmax = 0.51 e Å3
9345 reflectionsΔρmin = 0.47 e Å3
530 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)
O10.35999 (12)0.64057 (10)0.76160 (9)0.0464 (6)
O20.46517 (10)0.56399 (10)0.84766 (9)0.0386 (5)
N10.26812 (10)0.22756 (11)0.54074 (9)0.0226 (5)
N20.31920 (10)0.15565 (11)0.65403 (9)0.0230 (5)
C10.25545 (12)0.13717 (13)0.52362 (11)0.0229 (6)
C20.30723 (12)0.23573 (13)0.61920 (11)0.0222 (5)
C30.28623 (12)0.09338 (13)0.59526 (11)0.0224 (5)
C40.28431 (12)0.00269 (13)0.61516 (11)0.0237 (6)
C50.34480 (13)0.03739 (14)0.68160 (11)0.0269 (6)
C60.34347 (14)0.12801 (14)0.70058 (12)0.0299 (6)
C70.28312 (14)0.18565 (14)0.65308 (13)0.0321 (7)
C80.22224 (14)0.15158 (15)0.58780 (13)0.0349 (7)
C90.22164 (13)0.06108 (14)0.56960 (12)0.0300 (6)
C100.21672 (13)0.10645 (13)0.44218 (11)0.0247 (6)
C110.24996 (13)0.03092 (14)0.41210 (12)0.0290 (6)
C120.21196 (15)0.00247 (15)0.33582 (12)0.0346 (7)
C130.14243 (15)0.04930 (15)0.28740 (12)0.0364 (7)
C140.10969 (15)0.12467 (15)0.31610 (12)0.0347 (7)
C150.14608 (14)0.15236 (14)0.39315 (12)0.0284 (6)
C160.33102 (12)0.32180 (13)0.65973 (11)0.0225 (5)
C170.28642 (13)0.40108 (14)0.63137 (11)0.0263 (6)
C180.30953 (13)0.48151 (14)0.67087 (11)0.0274 (6)
C190.37744 (13)0.48436 (13)0.73951 (11)0.0257 (6)
C200.42279 (14)0.40575 (14)0.76760 (12)0.0325 (7)
C210.40007 (13)0.32554 (14)0.72791 (12)0.0307 (6)
C220.39888 (14)0.57134 (14)0.78239 (11)0.0284 (6)
C230.48580 (16)0.64419 (16)0.89787 (13)0.0398 (8)
C24A0.42436 (19)0.65330 (19)0.94755 (16)0.0411 (7)0.870 (4)
C25A0.4480 (2)0.6382 (2)1.02341 (17)0.0411 (7)0.870 (4)
C25B0.4084 (13)0.6533 (15)1.0086 (12)0.0411 (7)0.130 (4)
C24B0.4763 (12)0.6242 (13)0.9812 (9)0.0411 (7)0.130 (4)
O30.72389 (9)0.11506 (11)0.98995 (8)0.0361 (5)
O40.68567 (8)0.10185 (10)1.10449 (8)0.0288 (4)
N30.25961 (10)0.13099 (11)0.79692 (9)0.0218 (5)
N40.23280 (10)0.12800 (10)0.91440 (9)0.0219 (5)
C260.16917 (12)0.12879 (12)0.78295 (11)0.0217 (5)
C270.29565 (12)0.12908 (12)0.87613 (10)0.0210 (5)
C280.15348 (12)0.12699 (12)0.85661 (11)0.0213 (5)
C290.06818 (12)0.12799 (13)0.87721 (11)0.0224 (5)
C300.06319 (13)0.09824 (14)0.95100 (12)0.0280 (6)
C310.01582 (14)0.10342 (14)0.97286 (13)0.0323 (7)
C320.09136 (14)0.13606 (14)0.92102 (13)0.0315 (7)
C330.08745 (14)0.16429 (15)0.84699 (13)0.0338 (7)
C340.00862 (13)0.16088 (14)0.82550 (12)0.0303 (7)
C350.11146 (12)0.12649 (13)0.70215 (11)0.0222 (5)
C360.05572 (13)0.05385 (14)0.67653 (12)0.0278 (6)
C370.00288 (13)0.05064 (15)0.59948 (12)0.0319 (6)
C380.00694 (13)0.11936 (15)0.54765 (12)0.0323 (7)
C390.06174 (13)0.19250 (15)0.57282 (12)0.0305 (6)
C400.11339 (12)0.19657 (14)0.65014 (11)0.0261 (6)
C410.39055 (12)0.12569 (12)0.91330 (11)0.0210 (5)
C420.45320 (12)0.13070 (13)0.86928 (11)0.0240 (6)
C430.54253 (12)0.12645 (13)0.90681 (11)0.0245 (6)
C440.57150 (12)0.11583 (13)0.98811 (11)0.0226 (6)
C450.50929 (12)0.10990 (13)1.03207 (11)0.0240 (6)
C460.42025 (12)0.11466 (13)0.99490 (11)0.0242 (6)
C470.66770 (13)0.11106 (13)1.02562 (11)0.0259 (6)
C480.77829 (13)0.10768 (15)1.14775 (12)0.0324 (7)
C490.80374 (15)0.20428 (16)1.15957 (13)0.0384 (7)
C500.86523 (17)0.2423 (2)1.13349 (15)0.0527 (9)
H50.387200.001300.714100.0320*
H1N0.2592 (13)0.2721 (15)0.5047 (12)0.0270*
H80.180400.190700.555200.0420*
H60.384200.150500.746400.0360*
H70.283500.247900.665200.0380*
H120.233900.049900.316400.0420*
H130.117400.029800.234900.0440*
H140.062300.157500.283100.0420*
H150.122400.203400.412800.0340*
H170.239700.399800.584500.0320*
H180.278700.535000.650900.0330*
H200.469700.407200.814400.0390*
H210.431900.272400.747400.0370*
H23A0.546900.639700.931700.0480*
H23B0.482000.698200.864400.0480*
H24A0.365200.670800.923700.0490*0.870 (4)
H25A0.506900.620701.048300.0490*0.870 (4)
H25B0.406400.644801.053700.0490*0.870 (4)
H90.178100.038400.525600.0360*
H110.298700.000900.444100.0350*
H24B0.520900.589301.015500.0490*0.130 (4)
H25C0.362800.688400.975700.0490*0.130 (4)
H25D0.406300.638801.060600.0490*0.130 (4)
H3N0.2875 (14)0.1334 (14)0.7588 (12)0.0260*
H300.114200.074200.986800.0340*
H310.017800.084301.023900.0390*
H320.145200.139100.936000.0380*
H330.139200.186200.810700.0410*
H340.006900.181300.774800.0360*
H360.053700.006100.711800.0330*
H370.035900.001300.582600.0380*
H380.027900.116500.494700.0390*
H390.064000.239900.537200.0370*
H400.150100.247300.667500.0310*
H420.434400.137000.813600.0290*
H430.584500.130800.876600.0290*
H450.528300.102601.087600.0290*
H460.378500.110401.025300.0290*
H48A0.815300.077401.117800.0390*
H48B0.787600.077401.199400.0390*
H490.773000.240501.188100.0460*
H50A0.897300.208001.104800.0630*
H50B0.878000.304201.143200.0630*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0718 (12)0.0279 (9)0.0318 (9)0.0067 (8)0.0000 (8)0.0006 (7)
O20.0383 (9)0.0366 (9)0.0356 (9)0.0007 (7)0.0002 (7)0.0106 (7)
N10.0252 (8)0.0227 (8)0.0204 (8)0.0005 (7)0.0069 (7)0.0019 (7)
N20.0224 (8)0.0248 (8)0.0228 (8)0.0017 (7)0.0075 (7)0.0001 (7)
C10.0235 (10)0.0232 (10)0.0234 (10)0.0005 (8)0.0086 (8)0.0001 (8)
C20.0195 (9)0.0273 (10)0.0204 (9)0.0014 (8)0.0063 (7)0.0022 (8)
C30.0200 (9)0.0254 (10)0.0229 (9)0.0009 (8)0.0074 (7)0.0009 (8)
C40.0245 (10)0.0252 (10)0.0241 (10)0.0025 (8)0.0111 (8)0.0022 (8)
C50.0272 (10)0.0304 (11)0.0228 (10)0.0010 (8)0.0060 (8)0.0004 (8)
C60.0308 (11)0.0342 (12)0.0247 (10)0.0060 (9)0.0073 (8)0.0075 (9)
C70.0308 (11)0.0262 (11)0.0407 (12)0.0008 (9)0.0120 (9)0.0074 (9)
C80.0272 (11)0.0318 (12)0.0418 (13)0.0059 (9)0.0019 (9)0.0052 (10)
C90.0239 (10)0.0298 (11)0.0333 (11)0.0010 (8)0.0024 (8)0.0060 (9)
C100.0282 (10)0.0240 (10)0.0231 (10)0.0041 (8)0.0091 (8)0.0010 (8)
C110.0285 (10)0.0297 (11)0.0303 (11)0.0002 (9)0.0102 (9)0.0014 (9)
C120.0418 (13)0.0328 (12)0.0338 (12)0.0046 (10)0.0181 (10)0.0076 (9)
C130.0480 (14)0.0401 (13)0.0214 (10)0.0127 (11)0.0094 (10)0.0050 (9)
C140.0426 (13)0.0333 (12)0.0246 (11)0.0031 (10)0.0022 (9)0.0033 (9)
C150.0356 (11)0.0230 (10)0.0266 (10)0.0002 (8)0.0080 (9)0.0001 (8)
C160.0229 (9)0.0237 (10)0.0228 (9)0.0016 (8)0.0095 (8)0.0010 (8)
C170.0274 (10)0.0320 (11)0.0185 (9)0.0031 (8)0.0045 (8)0.0011 (8)
C180.0331 (11)0.0258 (10)0.0228 (10)0.0064 (9)0.0062 (8)0.0020 (8)
C190.0292 (10)0.0271 (11)0.0226 (10)0.0003 (8)0.0102 (8)0.0008 (8)
C200.0315 (11)0.0323 (12)0.0280 (11)0.0000 (9)0.0025 (9)0.0008 (9)
C210.0304 (11)0.0260 (11)0.0314 (11)0.0035 (9)0.0002 (9)0.0031 (9)
C220.0361 (11)0.0285 (11)0.0222 (10)0.0024 (9)0.0103 (9)0.0003 (8)
C230.0437 (14)0.0401 (13)0.0356 (12)0.0095 (11)0.0104 (10)0.0096 (10)
C24A0.0403 (13)0.0466 (12)0.0377 (10)0.0018 (10)0.0126 (9)0.0011 (9)
C25A0.0403 (13)0.0466 (12)0.0377 (10)0.0018 (10)0.0126 (9)0.0011 (9)
C25B0.0403 (13)0.0466 (12)0.0377 (10)0.0018 (10)0.0126 (9)0.0011 (9)
C24B0.0403 (13)0.0466 (12)0.0377 (10)0.0018 (10)0.0126 (9)0.0011 (9)
O30.0212 (7)0.0556 (10)0.0318 (8)0.0028 (7)0.0075 (6)0.0056 (7)
O40.0203 (7)0.0389 (8)0.0247 (7)0.0016 (6)0.0014 (5)0.0012 (6)
N30.0196 (8)0.0270 (9)0.0190 (8)0.0001 (7)0.0052 (6)0.0012 (6)
N40.0203 (8)0.0246 (8)0.0209 (8)0.0003 (6)0.0058 (6)0.0007 (6)
C260.0191 (9)0.0212 (9)0.0243 (10)0.0011 (7)0.0049 (7)0.0004 (7)
C270.0213 (9)0.0217 (9)0.0196 (9)0.0003 (7)0.0046 (7)0.0011 (7)
C280.0213 (9)0.0194 (9)0.0232 (9)0.0003 (7)0.0056 (7)0.0010 (7)
C290.0201 (9)0.0217 (9)0.0265 (10)0.0024 (7)0.0080 (8)0.0049 (8)
C300.0258 (10)0.0310 (11)0.0282 (10)0.0021 (8)0.0087 (8)0.0015 (9)
C310.0351 (12)0.0338 (12)0.0332 (11)0.0047 (9)0.0182 (9)0.0000 (9)
C320.0255 (10)0.0296 (11)0.0446 (13)0.0025 (9)0.0182 (9)0.0063 (9)
C330.0235 (10)0.0374 (12)0.0406 (12)0.0048 (9)0.0085 (9)0.0018 (10)
C340.0282 (11)0.0348 (12)0.0293 (11)0.0026 (9)0.0100 (9)0.0004 (9)
C350.0167 (9)0.0295 (10)0.0204 (9)0.0026 (8)0.0049 (7)0.0021 (8)
C360.0263 (10)0.0299 (11)0.0265 (10)0.0010 (8)0.0058 (8)0.0005 (8)
C370.0245 (10)0.0354 (12)0.0323 (11)0.0020 (9)0.0011 (9)0.0091 (9)
C380.0234 (10)0.0485 (14)0.0225 (10)0.0065 (9)0.0018 (8)0.0050 (9)
C390.0239 (10)0.0435 (13)0.0248 (10)0.0074 (9)0.0076 (8)0.0076 (9)
C400.0197 (9)0.0320 (11)0.0275 (10)0.0012 (8)0.0077 (8)0.0017 (8)
C410.0197 (9)0.0213 (9)0.0216 (9)0.0003 (7)0.0045 (7)0.0008 (7)
C420.0241 (10)0.0297 (11)0.0180 (9)0.0015 (8)0.0054 (8)0.0008 (8)
C430.0222 (9)0.0286 (10)0.0243 (10)0.0030 (8)0.0090 (8)0.0015 (8)
C440.0199 (9)0.0236 (10)0.0238 (10)0.0014 (8)0.0046 (7)0.0024 (8)
C450.0229 (10)0.0287 (10)0.0197 (9)0.0009 (8)0.0046 (7)0.0026 (8)
C460.0235 (10)0.0283 (10)0.0228 (10)0.0006 (8)0.0098 (8)0.0004 (8)
C470.0243 (10)0.0270 (10)0.0267 (10)0.0024 (8)0.0071 (8)0.0039 (8)
C480.0233 (10)0.0404 (13)0.0294 (11)0.0006 (9)0.0002 (8)0.0019 (9)
C490.0341 (12)0.0478 (14)0.0296 (12)0.0069 (10)0.0017 (9)0.0036 (10)
C500.0543 (16)0.0612 (18)0.0420 (14)0.0221 (14)0.0115 (12)0.0068 (13)
Geometric parameters (Å, º) top
O1—C221.205 (3)C20—H200.9500
O2—C221.338 (3)C21—H210.9500
O2—C231.470 (3)C23—H23A0.9900
O3—C471.211 (3)C23—H23B0.9900
O4—C481.457 (3)C24A—H24A0.9500
O4—C471.348 (2)C24B—H24B0.9500
N1—C11.382 (3)C25A—H25A0.9500
N1—C21.361 (2)C25A—H25B0.9500
N2—C31.384 (3)C25B—H25C0.9500
N2—C21.331 (3)C25B—H25D0.9500
N1—H1N0.90 (2)C26—C351.473 (3)
N3—C271.360 (2)C26—C281.381 (3)
N3—C261.377 (3)C27—C411.464 (3)
N4—C271.332 (3)C28—C291.476 (3)
N4—C281.387 (3)C29—C341.396 (3)
N3—H3N0.89 (2)C29—C301.393 (3)
C1—C101.475 (3)C30—C311.394 (3)
C1—C31.389 (3)C31—C321.382 (3)
C2—C161.467 (3)C32—C331.385 (3)
C3—C41.475 (3)C33—C341.387 (3)
C4—C91.398 (3)C35—C401.393 (3)
C4—C51.398 (3)C35—C361.390 (3)
C5—C61.391 (3)C36—C371.393 (3)
C6—C71.385 (3)C37—C381.383 (3)
C7—C81.384 (3)C38—C391.387 (3)
C8—C91.384 (3)C39—C401.391 (3)
C10—C151.393 (3)C41—C421.404 (3)
C10—C111.401 (3)C41—C461.398 (3)
C11—C121.385 (3)C42—C431.387 (3)
C12—C131.385 (3)C43—C441.392 (3)
C13—C141.384 (3)C44—C451.398 (3)
C14—C151.389 (3)C44—C471.484 (3)
C16—C171.396 (3)C45—C461.382 (3)
C16—C211.392 (3)C48—C491.493 (3)
C17—C181.384 (3)C49—C501.302 (4)
C18—C191.387 (3)C30—H300.9500
C19—C221.492 (3)C31—H310.9500
C19—C201.392 (3)C32—H320.9500
C20—C211.382 (3)C33—H330.9500
C23—C24B1.541 (16)C34—H340.9500
C23—C24A1.468 (4)C36—H360.9500
C24A—C25A1.308 (4)C37—H370.9500
C24B—C25B1.35 (3)C38—H380.9500
C5—H50.9500C39—H390.9500
C6—H60.9500C40—H400.9500
C7—H70.9500C42—H420.9500
C8—H80.9500C43—H430.9500
C9—H90.9500C45—H450.9500
C11—H110.9500C46—H460.9500
C12—H120.9500C48—H48A0.9900
C13—H130.9500C48—H48B0.9900
C14—H140.9500C49—H490.9500
C15—H150.9500C50—H50A0.9500
C17—H170.9500C50—H50B0.9500
C18—H180.9500
C22—O2—C23116.69 (17)C23—C24A—H24A119.00
C47—O4—C48116.30 (15)C25B—C24B—H24B118.00
C1—N1—C2108.00 (16)C23—C24B—H24B118.00
C2—N2—C3106.02 (15)C24A—C25A—H25A120.00
C1—N1—H1N125.1 (14)C24A—C25A—H25B120.00
C2—N1—H1N126.3 (14)H25A—C25A—H25B120.00
C26—N3—C27108.42 (16)H25C—C25B—H25D120.00
C27—N4—C28105.78 (15)C24B—C25B—H25D120.00
C27—N3—H3N128.0 (14)C24B—C25B—H25C120.00
C26—N3—H3N123.6 (14)N3—C26—C35121.24 (17)
N1—C1—C3105.27 (16)N3—C26—C28105.17 (16)
C3—C1—C10133.88 (18)C28—C26—C35133.57 (18)
N1—C1—C10120.86 (17)N3—C27—C41124.12 (17)
N1—C2—N2111.01 (17)N4—C27—C41125.19 (16)
N1—C2—C16124.12 (17)N3—C27—N4110.66 (16)
N2—C2—C16124.86 (17)C26—C28—C29128.75 (18)
N2—C3—C1109.68 (17)N4—C28—C26109.94 (17)
C1—C3—C4130.31 (18)N4—C28—C29121.25 (16)
N2—C3—C4119.95 (16)C30—C29—C34117.99 (18)
C5—C4—C9118.17 (18)C28—C29—C34121.91 (17)
C3—C4—C9121.47 (17)C28—C29—C30120.07 (17)
C3—C4—C5120.35 (17)C29—C30—C31120.69 (19)
C4—C5—C6120.62 (19)C30—C31—C32120.7 (2)
C5—C6—C7120.45 (19)C31—C32—C33119.1 (2)
C6—C7—C8119.3 (2)C32—C33—C34120.5 (2)
C7—C8—C9120.7 (2)C29—C34—C33121.08 (19)
C4—C9—C8120.76 (19)C26—C35—C36120.49 (17)
C1—C10—C15120.56 (18)C36—C35—C40119.32 (18)
C1—C10—C11121.07 (18)C26—C35—C40120.18 (17)
C11—C10—C15118.37 (18)C35—C36—C37120.44 (19)
C10—C11—C12120.19 (19)C36—C37—C38119.9 (2)
C11—C12—C13120.9 (2)C37—C38—C39120.14 (19)
C12—C13—C14119.50 (19)C38—C39—C40120.1 (2)
C13—C14—C15120.0 (2)C35—C40—C39120.15 (19)
C10—C15—C14121.1 (2)C42—C41—C46118.59 (18)
C2—C16—C21119.73 (18)C27—C41—C46119.36 (17)
C17—C16—C21118.62 (18)C27—C41—C42122.03 (17)
C2—C16—C17121.65 (17)C41—C42—C43120.17 (17)
C16—C17—C18120.71 (18)C42—C43—C44120.84 (18)
C17—C18—C19120.29 (19)C45—C44—C47121.90 (17)
C20—C19—C22121.56 (18)C43—C44—C45119.17 (18)
C18—C19—C20119.28 (18)C43—C44—C47118.93 (17)
C18—C19—C22119.15 (18)C44—C45—C46120.13 (17)
C19—C20—C21120.44 (19)C41—C46—C45121.10 (18)
C16—C21—C20120.65 (19)O3—C47—C44124.24 (17)
O1—C22—C19124.01 (19)O3—C47—O4123.59 (18)
O1—C22—O2123.33 (19)O4—C47—C44112.17 (17)
O2—C22—C19112.65 (17)O4—C48—C49108.94 (18)
O2—C23—C24B110.7 (7)C48—C49—C50124.5 (2)
O2—C23—C24A110.9 (2)C29—C30—H30120.00
C23—C24A—C25A122.4 (3)C31—C30—H30120.00
C23—C24B—C25B124.0 (15)C30—C31—H31120.00
C6—C5—H5120.00C32—C31—H31120.00
C4—C5—H5120.00C31—C32—H32120.00
C5—C6—H6120.00C33—C32—H32121.00
C7—C6—H6120.00C32—C33—H33120.00
C8—C7—H7120.00C34—C33—H33120.00
C6—C7—H7120.00C29—C34—H34120.00
C7—C8—H8120.00C33—C34—H34119.00
C9—C8—H8120.00C35—C36—H36120.00
C4—C9—H9120.00C37—C36—H36120.00
C8—C9—H9120.00C36—C37—H37120.00
C12—C11—H11120.00C38—C37—H37120.00
C10—C11—H11120.00C37—C38—H38120.00
C13—C12—H12120.00C39—C38—H38120.00
C11—C12—H12120.00C38—C39—H39120.00
C14—C13—H13120.00C40—C39—H39120.00
C12—C13—H13120.00C35—C40—H40120.00
C15—C14—H14120.00C39—C40—H40120.00
C13—C14—H14120.00C41—C42—H42120.00
C14—C15—H15119.00C43—C42—H42120.00
C10—C15—H15119.00C42—C43—H43120.00
C18—C17—H17120.00C44—C43—H43120.00
C16—C17—H17120.00C44—C45—H45120.00
C17—C18—H18120.00C46—C45—H45120.00
C19—C18—H18120.00C41—C46—H46119.00
C19—C20—H20120.00C45—C46—H46119.00
C21—C20—H20120.00O4—C48—H48A110.00
C16—C21—H21120.00O4—C48—H48B110.00
C20—C21—H21120.00C49—C48—H48A110.00
C24B—C23—H23A75.00C49—C48—H48B110.00
C24B—C23—H23B136.00H48A—C48—H48B108.00
O2—C23—H23B109.00C48—C49—H49118.00
O2—C23—H23A109.00C50—C49—H49118.00
H23A—C23—H23B108.00C49—C50—H50A120.00
C24A—C23—H23A109.00C49—C50—H50B120.00
C24A—C23—H23B109.00H50A—C50—H50B120.00
C25A—C24A—H24A119.00
C22—O2—C23—C24A80.2 (2)C16—C17—C18—C190.1 (3)
C23—O2—C22—O14.2 (3)C17—C18—C19—C22177.89 (19)
C23—O2—C22—C19174.53 (18)C17—C18—C19—C200.9 (3)
C48—O4—C47—C44172.67 (16)C20—C19—C22—O20.8 (3)
C47—O4—C48—C4981.7 (2)C22—C19—C20—C21178.2 (2)
C48—O4—C47—O37.2 (3)C18—C19—C22—O2179.55 (18)
C2—N1—C1—C31.7 (2)C20—C19—C22—O1177.9 (2)
C1—N1—C2—N21.1 (2)C18—C19—C22—O10.8 (3)
C2—N1—C1—C10177.97 (18)C18—C19—C20—C210.5 (3)
C1—N1—C2—C16179.83 (18)C19—C20—C21—C160.6 (3)
C3—N2—C2—C16178.73 (18)O2—C23—C24A—C25A107.8 (3)
C2—N2—C3—C4176.20 (17)N3—C26—C35—C4060.9 (3)
C3—N2—C2—N10.0 (2)N3—C26—C28—N40.0 (2)
C2—N2—C3—C11.1 (2)N3—C26—C35—C36118.0 (2)
C26—N3—C27—N41.6 (2)C28—C26—C35—C40121.2 (2)
C27—N3—C26—C280.9 (2)C35—C26—C28—C294.5 (3)
C27—N3—C26—C35177.55 (17)C28—C26—C35—C3660.0 (3)
C26—N3—C27—C41176.59 (17)C35—C26—C28—N4178.17 (19)
C28—N4—C27—C41176.64 (17)N3—C26—C28—C29177.26 (18)
C27—N4—C28—C29178.40 (17)N3—C27—C41—C424.7 (3)
C27—N4—C28—C260.9 (2)N3—C27—C41—C46173.48 (18)
C28—N4—C27—N31.5 (2)N4—C27—C41—C42177.41 (18)
C3—C1—C10—C15139.4 (2)N4—C27—C41—C464.4 (3)
N1—C1—C3—N21.7 (2)N4—C28—C29—C3023.0 (3)
C3—C1—C10—C1140.8 (3)N4—C28—C29—C34154.91 (18)
C10—C1—C3—C45.2 (4)C26—C28—C29—C30160.0 (2)
N1—C1—C10—C1541.0 (3)C26—C28—C29—C3422.1 (3)
N1—C1—C10—C11138.8 (2)C30—C29—C34—C330.3 (3)
N1—C1—C3—C4175.22 (19)C34—C29—C30—C311.6 (3)
C10—C1—C3—N2177.9 (2)C28—C29—C34—C33177.64 (19)
N2—C2—C16—C17152.4 (2)C28—C29—C30—C31176.44 (18)
N1—C2—C16—C21153.30 (19)C29—C30—C31—C321.7 (3)
N1—C2—C16—C1726.2 (3)C30—C31—C32—C330.5 (3)
N2—C2—C16—C2128.1 (3)C31—C32—C33—C340.8 (3)
C1—C3—C4—C924.5 (3)C32—C33—C34—C290.9 (3)
N2—C3—C4—C526.6 (3)C36—C35—C40—C391.7 (3)
C1—C3—C4—C5156.7 (2)C26—C35—C36—C37178.30 (19)
N2—C3—C4—C9152.21 (19)C40—C35—C36—C370.6 (3)
C5—C4—C9—C83.0 (3)C26—C35—C40—C39177.17 (18)
C3—C4—C5—C6179.84 (19)C35—C36—C37—C381.1 (3)
C3—C4—C9—C8178.20 (19)C36—C37—C38—C391.7 (3)
C9—C4—C5—C61.3 (3)C37—C38—C39—C400.6 (3)
C4—C5—C6—C71.2 (3)C38—C39—C40—C351.2 (3)
C5—C6—C7—C82.0 (3)C27—C41—C46—C45179.10 (18)
C6—C7—C8—C90.4 (3)C42—C41—C46—C450.8 (3)
C7—C8—C9—C42.2 (3)C27—C41—C42—C43179.44 (18)
C1—C10—C11—C12179.2 (2)C46—C41—C42—C431.2 (3)
C15—C10—C11—C121.0 (3)C41—C42—C43—C441.0 (3)
C1—C10—C15—C14179.3 (2)C42—C43—C44—C450.3 (3)
C11—C10—C15—C140.5 (3)C42—C43—C44—C47179.62 (18)
C10—C11—C12—C131.8 (3)C43—C44—C47—O4179.25 (17)
C11—C12—C13—C141.0 (3)C45—C44—C47—O3179.3 (2)
C12—C13—C14—C150.5 (3)C45—C44—C47—O40.8 (3)
C13—C14—C15—C101.3 (3)C43—C44—C47—O30.7 (3)
C2—C16—C17—C18179.52 (19)C43—C44—C45—C460.1 (3)
C17—C16—C21—C201.3 (3)C47—C44—C45—C46180.00 (19)
C2—C16—C21—C20179.13 (19)C44—C45—C46—C410.2 (3)
C21—C16—C17—C180.9 (3)O4—C48—C49—C50120.0 (2)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the N1/N2/C1–C3 1H-imidazole ring and the C4–C9 and C10–C15 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N···N4i0.90 (2)2.14 (2)3.037 (2)176 (2)
N3—H3N···N20.89 (2)2.06 (2)2.925 (2)164 (2)
C7—H7···O1ii0.952.453.254 (3)142
C20—H20···O20.952.412.736 (3)100
C32—H32···O3iii0.952.513.439 (3)167
C46—H46···N40.952.602.921 (3)100
C23—H23A···Cg1iv0.992.743.524 (3)136
C25A—H25B···Cg2v0.952.793.687 (3)158
C37—H37···Cg3vi0.952.903.634 (3)134
C25B—H25D···Cg2v0.952.683.44 (2)137
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y1, z; (iii) x1, y, z; (iv) x+1, y+1/2, z+3/2; (v) x, y+1/2, z+1/2; (vi) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC25H20N2O2
Mr380.43
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)15.705 (5), 14.888 (5), 17.589 (6)
β (°) 105.151 (4)
V3)3970 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.73 × 0.35 × 0.15
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.967, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
46196, 9345, 6507
Rint0.064
(sin θ/λ)max1)0.663
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.149, 1.02
No. of reflections9345
No. of parameters530
No. of restraints42
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.51, 0.47

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the N1/N2/C1–C3 1H-imidazole ring and the C4–C9 and C10–C15 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N···N4i0.90 (2)2.14 (2)3.037 (2)176 (2)
N3—H3N···N20.89 (2)2.06 (2)2.925 (2)164 (2)
C7—H7···O1ii0.952.453.254 (3)142
C32—H32···O3iii0.952.513.439 (3)167
C23—H23A···Cg1iv0.992.743.524 (3)136
C25A—H25B···Cg2v0.952.793.687 (3)158
C37—H37···Cg3vi0.952.903.634 (3)134
C25B—H25D···Cg2v0.952.683.44 (2)137
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y1, z; (iii) x1, y, z; (iv) x+1, y+1/2, z+3/2; (v) x, y+1/2, z+1/2; (vi) x, y, z+1.
 

Acknowledgements

Manchester Metropolitan University, Erciyes University and Granada University are gratefully acknowledged for supporting this study. The authors also thank José Romero Garzón, Centro de Instrumentación Científica, Universidad de Granada, for the data collection.

References

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Volume 69| Part 7| July 2013| Pages o1105-o1106
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