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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 6| June 2013| Pages o875-o876

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

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, eDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada, E-18071, Spain, and fChemistry Department, Faculty of Science, Sohag University, 82524 Shag, Egypt
*Correspondence e-mail: shaabankamel@yahoo.com

(Received 7 May 2013; accepted 8 May 2013; online 11 May 2013)

The title compound, C24H19ClN2, crystallizes with two independent mol­ecules in the asymmetric unit. The prop-2-enyl substituents on the imidazole rings adopt similar conformations in the two mol­ecules. The 4-and 5-substituted phenyl rings and the benzene ring make dihedral angles of 67.06 (8), 5.61 (8) and 41.09 (8)°, respectively, with the imadazole ring in one mol­ecule and 71.53 (8), 28.85 (8) and 41.87 (8)°, respectively, in the other. The crystal structure features C—H⋯π inter­actions and weak ππ stacking inter­actions [centroid–centroid distances = 3.6937 (10) and 4.0232 (10) Å] between the chloro­phenyl rings, which form a three-dimensional supramolecular structure.

Related literature

For pharmaceutical properties of imidazoles and imidazole-containing compounds, see, for example: Roman et al. (2007[Roman, G., Riley, J. G., Vlahakis, J. Z., Kinobe, R. T., Brien, J. F., Nakatsu, K. & Szarek, W. A. (2007). Bioorg. Med. Chem. 15, 3225-3234.]); Nanterment et al. (2004[Nanterment, P. G., Barrow, J. C., Lindsley, S. R., Young, M., Mao, S., Carroll, S., Bailey, C., Bosserman, M., Colussi, D., McMasters, D. R., Vacca, J. P. & Selnick, H. G. (2004). Bioorg. Med. Chem. Lett. 14, 2141-2145.]); Congiu et al. (2008[Congiu, C., Cocco, M. T. & Onnis, V. (2008). Bioorg. Med. Chem. Lett. 18, 989-993.]); Venkatesan et al. (2008[Venkatesan, A. M., Agarwal, A., Abe, T., Ushirogochi, H. O., Santos, D., Li, Z., Francisco, G., Lin, Y. I., Peterson, P. J., Yang, Y., Weiss, W. J., Shales, D. M. & Mansour, T. S. (2008). Bioorg. Med. Chem. 16, 1890-1902.]); Bhatnagar et al. (2011[Bhatnagar, A., Sharma, P. K. & Kumar, N. (2011). Int. J. Pharm. Tech. Res. 3, 268-282.]); Puratchikody & Doble (2007[Puratchikody, A. & Doble, M. (2007). Bioorg. Med. Chem. Lett. 15, 1083-1090.]). For similar structures, see: Mohamed et al. (2013[Mohamed, S. K., Akkurt, M., Marzouk, A. A., Abbasov, V. M. & Gurbanov, A. V. (2013). Acta Cryst. E69, o474-o475.]); Akkurt et al. (2013[Akkurt, M., Fronczek, F. R., Mohamed, S. K., Talybov, A. H., Marzouk, A. A. E. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o527-o528.]).

[Scheme 1]

Experimental

Crystal data
  • C24H19ClN2

  • Mr = 370.86

  • Triclinic, [P \overline 1]

  • a = 10.0916 (7) Å

  • b = 13.1386 (9) Å

  • c = 15.6155 (10) Å

  • α = 72.924 (1)°

  • β = 86.849 (1)°

  • γ = 71.830 (1)°

  • V = 1879.0 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 100 K

  • 0.57 × 0.33 × 0.28 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 = 0.919, Tmax = 0.942

  • 20791 measured reflections

  • 7718 independent reflections

  • 6764 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.106

  • S = 1.07

  • 7718 reflections

  • 487 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg4 and Cg8 are the centroids of the C4–C9, C19–C24 and C43–C48 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5⋯Cg4i 0.95 2.76 3.5968 (17) 147
C11—H11⋯Cg8ii 0.95 2.83 3.5879 (19) 137
C33—H33⋯Cg2iii 0.95 2.89 3.8217 (18) 166
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y, -z+1; (iii) 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: 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

Imidazoles have been intensivley reported to serve as usefull building blocks for synthesis of diverse class of bioactive molecules. In addition imidazole comtaining compounds exhibited a wide spectrum of pharmaceutical properties such as pesticides, fungicides, antibacterial anti-inflammatory, anti-tubercular, anti-diabetic, antimalarial and antitumour (Roman et al., 2007; Nanterment et al., 2004; Congiu et al., 2008; Venkatesan et al., 2008; Bhatnagar et al., 2011; Puratchikody & Doble 2007). In this aspect and further to our study on synthesis of tetrasubstituted imidazoles as potential bioactive molecules, we herein report the crystal structure of the title compound.

As seen in the Fig. 1, the title compound contains two independent molecules, 1 (with Cl1) and 2 (with Cl2), in the asymmetric unit. The prop-2-ene substituents on the imidazole rings adopt similar conformations in molecules 1 and 2. The 4-and 5-substituted phenyl rings (C4–C9 and C19–C24) and the benzene ring (C13–C18) attached to the atom Cl1 makes dihedral angles of 67.06 (8), 5.61 (8) and 41.09 (8)°, respectively, with the imadazole ring (N1/N2/C1–C3) of molecule 1 and the corresponding angles are A/B = 71.53 (8), A/C = 28.85 (8) and A/D = 41.87 (8)°, respectively, in molecule 2; where A (N3/N4/C25–C27), B (C28–C33), C (C43–C48) and D (C37–C42). All bond lengths are normal and are comparable with those reported for the similar structures (Mohamed et al., 2013; Akkurt et al., 2013).

The crystal structure is stabilized by C—H···π interactions (Table 1) and weak π-π stacking interactions [Cg3···Cg3 (-x, -y, 1 - z) = 3.6937 (10) Å and Cg7···Cg7 (-x, 1 - y, 1 - z) = 4.0232 (10) Å; where Cg3 and Cg7 are the centroids of the C13–C18 and C37–C42 benzene rings respectively, which are attached to the Cl1 and Cl2 atoms]. Fig. 2 shows the packing diagram of (I) along the a axis.

Related literature top

For pharmaceutical properties of imidazoles and imidazole-containing compounds, see, for example: Roman et al. (2007); Nanterment et al. (2004); Congiu et al. (2008); Venkatesan et al. (2008); Bhatnagar et al. (2011); Puratchikody & Doble (2007). For similar structures, see: Mohamed et al. (2013); Akkurt et al. (2013).

Experimental top

The title compound was prepared, according to our reported method (Mohamed et al., 2013) in 81% yield. Suitable single crystals were obtained by slow evaporation of a solution in ethanol, m.p. 305–307 K.

Refinement top

All H atoms were placed in geometrically, with C—H = 0.95 and 0.99 Å, and refined as riding with Uiso(H) = 1.2 Ueq(C) of the parent atom.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (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. View of the two molecules of the title compound in the asymmetric unit with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of the packing diagram of the title compound viewing along the a axis
2-(4-Chlorophenyl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole top
Crystal data top
C24H19ClN2Z = 4
Mr = 370.86F(000) = 776
Triclinic, P1Dx = 1.311 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0916 (7) ÅCell parameters from 9362 reflections
b = 13.1386 (9) Åθ = 4.6–55.6°
c = 15.6155 (10) ŵ = 0.21 mm1
α = 72.924 (1)°T = 100 K
β = 86.849 (1)°Prism, colourless
γ = 71.830 (1)°0.57 × 0.33 × 0.28 mm
V = 1879.0 (2) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
7718 independent reflections
Radiation source: sealed tube6764 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
phi and ω scansθmax = 26.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1212
Tmin = 0.919, Tmax = 0.942k = 1616
20791 measured reflectionsl = 1919
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0514P)2 + 0.7786P]
where P = (Fo2 + 2Fc2)/3
7718 reflections(Δ/σ)max = 0.001
487 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C24H19ClN2γ = 71.830 (1)°
Mr = 370.86V = 1879.0 (2) Å3
Triclinic, P1Z = 4
a = 10.0916 (7) ÅMo Kα radiation
b = 13.1386 (9) ŵ = 0.21 mm1
c = 15.6155 (10) ÅT = 100 K
α = 72.924 (1)°0.57 × 0.33 × 0.28 mm
β = 86.849 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
7718 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
6764 reflections with I > 2σ(I)
Tmin = 0.919, Tmax = 0.942Rint = 0.023
20791 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.07Δρmax = 0.34 e Å3
7718 reflectionsΔρmin = 0.23 e Å3
487 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
Cl10.20646 (4)0.09006 (3)0.65803 (2)0.0300 (1)
N10.02163 (12)0.17529 (10)0.21321 (8)0.0200 (3)
N20.06068 (12)0.28573 (10)0.26375 (8)0.0200 (3)
C10.00889 (14)0.21232 (12)0.28437 (10)0.0197 (4)
C20.09418 (14)0.29822 (11)0.17502 (9)0.0189 (4)
C30.04422 (14)0.22994 (12)0.14208 (9)0.0196 (4)
C40.05483 (15)0.20489 (12)0.05485 (10)0.0203 (4)
C50.01427 (15)0.28619 (12)0.02220 (10)0.0218 (4)
C60.00411 (15)0.26283 (13)0.10377 (10)0.0233 (4)
C70.07436 (16)0.15777 (13)0.10974 (10)0.0259 (4)
C80.14332 (17)0.07618 (13)0.03361 (11)0.0276 (4)
C90.13453 (16)0.09918 (13)0.04827 (10)0.0249 (4)
C100.09628 (16)0.09705 (13)0.20987 (10)0.0238 (4)
C110.24612 (17)0.15345 (14)0.17687 (10)0.0277 (5)
C120.30685 (17)0.26199 (14)0.14500 (11)0.0301 (5)
C130.06083 (15)0.17650 (12)0.37484 (10)0.0202 (4)
C140.02610 (16)0.16120 (12)0.44742 (10)0.0227 (4)
C150.01711 (16)0.13543 (12)0.53460 (10)0.0237 (4)
C160.14858 (16)0.12304 (12)0.54890 (10)0.0222 (4)
C170.23644 (16)0.13630 (13)0.47904 (10)0.0239 (4)
C180.19289 (16)0.16348 (13)0.39192 (10)0.0240 (4)
C190.17971 (14)0.37187 (11)0.13467 (10)0.0195 (4)
C200.22749 (15)0.42241 (12)0.18880 (10)0.0221 (4)
C210.31189 (16)0.48977 (12)0.15487 (10)0.0238 (4)
C220.35045 (15)0.50794 (12)0.06640 (11)0.0244 (4)
C230.30485 (16)0.45768 (13)0.01221 (10)0.0249 (5)
C240.22005 (15)0.39068 (12)0.04585 (10)0.0229 (4)
Cl20.42972 (4)0.65508 (3)0.50155 (3)0.0334 (1)
N30.19935 (12)0.35109 (10)0.73274 (8)0.0194 (3)
N40.17457 (12)0.23629 (10)0.65869 (8)0.0205 (3)
C250.11724 (15)0.33401 (12)0.67463 (9)0.0201 (4)
C260.29983 (15)0.18823 (12)0.70807 (9)0.0197 (4)
C270.31680 (14)0.25751 (12)0.75442 (9)0.0192 (4)
C280.43246 (15)0.24556 (11)0.81453 (10)0.0195 (4)
C290.56009 (16)0.25167 (13)0.77852 (10)0.0236 (4)
C300.67230 (16)0.23572 (13)0.83402 (11)0.0261 (4)
C310.65703 (16)0.21555 (13)0.92575 (11)0.0259 (5)
C320.53069 (17)0.20896 (13)0.96205 (10)0.0269 (4)
C330.41862 (16)0.22345 (13)0.90689 (10)0.0239 (4)
C340.17099 (16)0.44544 (13)0.77037 (10)0.0243 (5)
C350.25101 (17)0.52512 (13)0.72946 (12)0.0310 (5)
C360.33377 (19)0.52130 (15)0.66240 (14)0.0399 (6)
C370.01782 (15)0.41483 (12)0.63418 (9)0.0202 (4)
C380.12790 (16)0.37477 (13)0.62550 (10)0.0246 (4)
C390.25512 (16)0.44770 (13)0.58485 (11)0.0277 (5)
C400.27089 (15)0.56125 (13)0.55261 (10)0.0245 (4)
C410.16323 (16)0.60279 (13)0.55934 (10)0.0230 (4)
C420.03662 (16)0.52952 (12)0.60013 (9)0.0218 (4)
C430.39728 (15)0.07904 (12)0.70529 (10)0.0202 (4)
C440.48893 (15)0.00912 (12)0.77813 (10)0.0222 (4)
C450.58242 (16)0.09211 (13)0.77391 (11)0.0256 (4)
C460.58688 (16)0.12606 (13)0.69738 (11)0.0273 (5)
C470.49576 (17)0.05782 (13)0.62534 (11)0.0279 (5)
C480.40109 (16)0.04347 (13)0.62921 (10)0.0251 (5)
H50.068800.358200.018700.0260*
H60.051100.319000.155800.0280*
H70.080800.141800.165600.0310*
H80.196900.004100.037500.0330*
H90.182700.043000.100000.0300*
H10A0.093400.044900.270700.0290*
H10B0.047300.052100.170000.0290*
H110.301900.106400.179300.0330*
H12A0.255100.312300.141300.0360*
H12B0.402400.290100.125600.0360*
H140.116600.168700.436600.0270*
H150.041900.126500.583400.0280*
H170.325900.126900.490600.0290*
H180.253200.173300.343500.0290*
H200.201900.410500.249600.0260*
H210.343300.523500.192500.0290*
H220.407600.554400.043100.0290*
H230.331700.469100.048300.0300*
H240.189100.357200.007900.0270*
H290.570500.266900.715600.0280*
H300.759600.238600.809100.0310*
H310.733100.206300.963600.0310*
H320.520500.194501.024900.0320*
H330.332400.218300.932300.0290*
H34A0.193700.415600.835600.0290*
H34B0.070000.487100.762000.0290*
H350.240600.584500.754800.0370*
H36A0.347700.463500.634700.0480*
H36B0.380000.576300.641300.0480*
H380.115700.296800.647600.0290*
H390.329900.420200.579300.0330*
H410.175700.680700.536300.0280*
H420.037900.557600.604900.0260*
H440.487000.031300.831000.0270*
H450.643900.138500.823800.0310*
H460.651400.195100.694400.0330*
H470.498000.080500.572700.0330*
H480.338500.088800.579600.0300*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0315 (2)0.0358 (2)0.0215 (2)0.0115 (2)0.0067 (2)0.0067 (2)
N10.0199 (6)0.0201 (6)0.0199 (6)0.0079 (5)0.0001 (5)0.0038 (5)
N20.0186 (6)0.0195 (6)0.0207 (6)0.0055 (5)0.0020 (5)0.0047 (5)
C10.0172 (7)0.0189 (7)0.0215 (7)0.0042 (5)0.0004 (5)0.0049 (5)
C20.0163 (7)0.0181 (7)0.0197 (7)0.0028 (5)0.0002 (5)0.0044 (5)
C30.0173 (7)0.0189 (7)0.0201 (7)0.0046 (5)0.0006 (5)0.0030 (5)
C40.0191 (7)0.0225 (7)0.0220 (7)0.0102 (6)0.0018 (5)0.0066 (6)
C50.0182 (7)0.0224 (7)0.0259 (8)0.0078 (6)0.0016 (6)0.0074 (6)
C60.0204 (7)0.0293 (8)0.0210 (7)0.0116 (6)0.0003 (6)0.0041 (6)
C70.0292 (8)0.0322 (8)0.0227 (7)0.0158 (7)0.0046 (6)0.0113 (6)
C80.0313 (8)0.0221 (7)0.0312 (8)0.0082 (6)0.0049 (7)0.0110 (6)
C90.0275 (8)0.0211 (7)0.0247 (8)0.0076 (6)0.0003 (6)0.0043 (6)
C100.0278 (8)0.0232 (7)0.0236 (7)0.0133 (6)0.0010 (6)0.0058 (6)
C110.0285 (8)0.0352 (9)0.0242 (8)0.0179 (7)0.0012 (6)0.0067 (7)
C120.0266 (8)0.0364 (9)0.0278 (8)0.0096 (7)0.0040 (6)0.0094 (7)
C130.0221 (7)0.0173 (7)0.0212 (7)0.0064 (6)0.0014 (6)0.0052 (5)
C140.0217 (7)0.0219 (7)0.0257 (8)0.0087 (6)0.0012 (6)0.0065 (6)
C150.0258 (8)0.0238 (7)0.0226 (7)0.0086 (6)0.0008 (6)0.0072 (6)
C160.0270 (8)0.0191 (7)0.0198 (7)0.0073 (6)0.0047 (6)0.0051 (6)
C170.0201 (7)0.0257 (8)0.0263 (8)0.0087 (6)0.0038 (6)0.0071 (6)
C180.0223 (7)0.0248 (7)0.0243 (8)0.0076 (6)0.0017 (6)0.0055 (6)
C190.0161 (7)0.0159 (6)0.0239 (7)0.0028 (5)0.0006 (5)0.0044 (5)
C200.0212 (7)0.0217 (7)0.0227 (7)0.0058 (6)0.0019 (6)0.0065 (6)
C210.0225 (7)0.0215 (7)0.0293 (8)0.0072 (6)0.0013 (6)0.0093 (6)
C220.0195 (7)0.0216 (7)0.0318 (8)0.0092 (6)0.0037 (6)0.0048 (6)
C230.0244 (8)0.0258 (8)0.0240 (8)0.0089 (6)0.0048 (6)0.0059 (6)
C240.0240 (8)0.0229 (7)0.0232 (7)0.0088 (6)0.0012 (6)0.0074 (6)
Cl20.0213 (2)0.0305 (2)0.0393 (2)0.0009 (2)0.0062 (2)0.0029 (2)
N30.0187 (6)0.0195 (6)0.0189 (6)0.0043 (5)0.0008 (5)0.0054 (5)
N40.0191 (6)0.0219 (6)0.0190 (6)0.0057 (5)0.0006 (5)0.0043 (5)
C250.0199 (7)0.0224 (7)0.0183 (7)0.0074 (6)0.0015 (5)0.0056 (6)
C260.0192 (7)0.0203 (7)0.0176 (7)0.0057 (6)0.0002 (5)0.0029 (5)
C270.0174 (7)0.0200 (7)0.0188 (7)0.0053 (5)0.0012 (5)0.0040 (5)
C280.0198 (7)0.0163 (7)0.0229 (7)0.0050 (5)0.0019 (5)0.0064 (5)
C290.0238 (8)0.0247 (7)0.0221 (7)0.0078 (6)0.0010 (6)0.0062 (6)
C300.0210 (7)0.0277 (8)0.0311 (8)0.0094 (6)0.0006 (6)0.0087 (6)
C310.0248 (8)0.0238 (8)0.0292 (8)0.0074 (6)0.0069 (6)0.0066 (6)
C320.0305 (8)0.0304 (8)0.0210 (7)0.0111 (7)0.0013 (6)0.0070 (6)
C330.0229 (8)0.0264 (8)0.0235 (7)0.0085 (6)0.0022 (6)0.0084 (6)
C340.0230 (8)0.0249 (8)0.0253 (8)0.0040 (6)0.0018 (6)0.0110 (6)
C350.0282 (8)0.0216 (8)0.0436 (10)0.0056 (6)0.0063 (7)0.0110 (7)
C360.0366 (10)0.0293 (9)0.0537 (12)0.0145 (8)0.0069 (8)0.0083 (8)
C370.0198 (7)0.0236 (7)0.0163 (7)0.0041 (6)0.0005 (5)0.0071 (6)
C380.0249 (8)0.0218 (7)0.0254 (8)0.0066 (6)0.0000 (6)0.0050 (6)
C390.0204 (8)0.0299 (8)0.0320 (8)0.0090 (6)0.0023 (6)0.0058 (7)
C400.0192 (7)0.0266 (8)0.0227 (7)0.0016 (6)0.0013 (6)0.0054 (6)
C410.0254 (8)0.0206 (7)0.0207 (7)0.0044 (6)0.0002 (6)0.0055 (6)
C420.0228 (7)0.0244 (7)0.0197 (7)0.0078 (6)0.0007 (6)0.0079 (6)
C430.0178 (7)0.0198 (7)0.0243 (7)0.0080 (6)0.0014 (6)0.0060 (6)
C440.0212 (7)0.0222 (7)0.0241 (7)0.0091 (6)0.0001 (6)0.0053 (6)
C450.0203 (7)0.0231 (7)0.0303 (8)0.0057 (6)0.0029 (6)0.0038 (6)
C460.0218 (8)0.0217 (7)0.0380 (9)0.0042 (6)0.0010 (6)0.0107 (7)
C470.0270 (8)0.0283 (8)0.0322 (8)0.0075 (7)0.0004 (6)0.0154 (7)
C480.0240 (8)0.0244 (8)0.0257 (8)0.0054 (6)0.0039 (6)0.0068 (6)
Geometric parameters (Å, º) top
Cl1—C161.7458 (16)C18—H180.9500
Cl2—C401.7480 (17)C20—H200.9500
N1—C11.364 (2)C21—H210.9500
N1—C31.3925 (19)C22—H220.9500
N1—C101.465 (2)C23—H230.9500
N2—C21.3822 (18)C24—H240.9500
N2—C11.320 (2)C25—C371.477 (2)
N3—C341.467 (2)C26—C271.371 (2)
N3—C271.386 (2)C26—C431.476 (2)
N3—C251.3706 (19)C27—C281.479 (2)
N4—C251.324 (2)C28—C291.393 (2)
N4—C261.384 (2)C28—C331.393 (2)
C1—C131.475 (2)C29—C301.389 (2)
C2—C191.477 (2)C30—C311.387 (2)
C2—C31.380 (2)C31—C321.384 (2)
C3—C41.483 (2)C32—C331.391 (2)
C4—C51.396 (2)C34—C351.495 (2)
C4—C91.402 (2)C35—C361.306 (3)
C5—C61.387 (2)C37—C381.397 (2)
C6—C71.388 (2)C37—C421.397 (2)
C7—C81.387 (2)C38—C391.391 (2)
C8—C91.390 (2)C39—C401.387 (2)
C10—C111.505 (2)C40—C411.380 (2)
C11—C121.315 (3)C41—C421.388 (2)
C13—C141.400 (2)C43—C441.402 (2)
C13—C181.397 (2)C43—C481.393 (2)
C14—C151.384 (2)C44—C451.388 (2)
C15—C161.385 (2)C45—C461.387 (2)
C16—C171.380 (2)C46—C471.386 (2)
C17—C181.385 (2)C47—C481.391 (2)
C19—C201.401 (2)C29—H290.9500
C19—C241.396 (2)C30—H300.9500
C20—C211.391 (2)C31—H310.9500
C21—C221.386 (2)C32—H320.9500
C22—C231.387 (2)C33—H330.9500
C23—C241.390 (2)C34—H34A0.9900
C5—H50.9500C34—H34B0.9900
C6—H60.9500C35—H350.9500
C7—H70.9500C36—H36A0.9500
C8—H80.9500C36—H36B0.9500
C9—H90.9500C38—H380.9500
C10—H10A0.9900C39—H390.9500
C10—H10B0.9900C41—H410.9500
C11—H110.9500C42—H420.9500
C12—H12B0.9500C44—H440.9500
C12—H12A0.9500C45—H450.9500
C14—H140.9500C46—H460.9500
C15—H150.9500C47—H470.9500
C17—H170.9500C48—H480.9500
C1—N1—C3107.20 (12)C24—C23—H23120.00
C1—N1—C10126.91 (12)C22—C23—H23120.00
C3—N1—C10125.83 (12)C19—C24—H24120.00
C1—N2—C2106.30 (12)C23—C24—H24120.00
C27—N3—C34124.52 (12)N3—C25—N4111.56 (13)
C25—N3—C27106.76 (12)N3—C25—C37124.29 (14)
C25—N3—C34128.66 (13)N4—C25—C37124.15 (13)
C25—N4—C26105.60 (12)N4—C26—C27110.18 (13)
N1—C1—C13126.68 (14)N4—C26—C43121.86 (13)
N2—C1—C13121.93 (14)C27—C26—C43127.93 (14)
N1—C1—N2111.38 (13)N3—C27—C26105.91 (13)
N2—C2—C3109.72 (12)N3—C27—C28123.01 (13)
N2—C2—C19118.31 (13)C26—C27—C28131.07 (14)
C3—C2—C19131.84 (13)C27—C28—C29119.28 (13)
N1—C3—C2105.40 (12)C27—C28—C33121.48 (14)
N1—C3—C4121.12 (13)C29—C28—C33119.18 (14)
C2—C3—C4133.41 (13)C28—C29—C30120.42 (14)
C3—C4—C9120.62 (13)C29—C30—C31120.05 (15)
C5—C4—C9118.78 (14)C30—C31—C32119.84 (15)
C3—C4—C5120.61 (14)C31—C32—C33120.30 (14)
C4—C5—C6120.60 (15)C28—C33—C32120.20 (15)
C5—C6—C7120.34 (14)N3—C34—C35114.07 (13)
C6—C7—C8119.61 (14)C34—C35—C36126.56 (17)
C7—C8—C9120.41 (16)C25—C37—C38119.00 (14)
C4—C9—C8120.26 (15)C25—C37—C42121.96 (14)
N1—C10—C11113.67 (14)C38—C37—C42118.96 (14)
C10—C11—C12125.92 (17)C37—C38—C39120.79 (15)
C1—C13—C18124.28 (14)C38—C39—C40118.82 (15)
C14—C13—C18118.67 (14)Cl2—C40—C39119.90 (13)
C1—C13—C14116.95 (14)Cl2—C40—C41118.58 (13)
C13—C14—C15121.38 (15)C39—C40—C41121.53 (15)
C14—C15—C16118.29 (15)C40—C41—C42119.34 (15)
Cl1—C16—C15119.59 (12)C37—C42—C41120.57 (15)
C15—C16—C17121.89 (14)C26—C43—C44121.28 (13)
Cl1—C16—C17118.52 (13)C26—C43—C48120.42 (14)
C16—C17—C18119.38 (15)C44—C43—C48118.30 (14)
C13—C18—C17120.39 (15)C43—C44—C45120.76 (14)
C20—C19—C24117.97 (14)C44—C45—C46120.53 (15)
C2—C19—C20118.62 (13)C45—C46—C47119.06 (16)
C2—C19—C24123.36 (13)C46—C47—C48120.79 (15)
C19—C20—C21120.95 (14)C43—C48—C47120.55 (15)
C20—C21—C22120.31 (14)C28—C29—H29120.00
C21—C22—C23119.37 (15)C30—C29—H29120.00
C22—C23—C24120.43 (14)C29—C30—H30120.00
C19—C24—C23120.96 (14)C31—C30—H30120.00
C4—C5—H5120.00C30—C31—H31120.00
C6—C5—H5120.00C32—C31—H31120.00
C5—C6—H6120.00C31—C32—H32120.00
C7—C6—H6120.00C33—C32—H32120.00
C8—C7—H7120.00C28—C33—H33120.00
C6—C7—H7120.00C32—C33—H33120.00
C7—C8—H8120.00N3—C34—H34A109.00
C9—C8—H8120.00N3—C34—H34B109.00
C8—C9—H9120.00C35—C34—H34A109.00
C4—C9—H9120.00C35—C34—H34B109.00
C11—C10—H10A109.00H34A—C34—H34B108.00
N1—C10—H10B109.00C34—C35—H35117.00
C11—C10—H10B109.00C36—C35—H35117.00
H10A—C10—H10B108.00C35—C36—H36A120.00
N1—C10—H10A109.00C35—C36—H36B120.00
C10—C11—H11117.00H36A—C36—H36B120.00
C12—C11—H11117.00C37—C38—H38120.00
C11—C12—H12A120.00C39—C38—H38120.00
C11—C12—H12B120.00C38—C39—H39121.00
H12A—C12—H12B120.00C40—C39—H39121.00
C15—C14—H14119.00C40—C41—H41120.00
C13—C14—H14119.00C42—C41—H41120.00
C14—C15—H15121.00C37—C42—H42120.00
C16—C15—H15121.00C41—C42—H42120.00
C18—C17—H17120.00C43—C44—H44120.00
C16—C17—H17120.00C45—C44—H44120.00
C17—C18—H18120.00C44—C45—H45120.00
C13—C18—H18120.00C46—C45—H45120.00
C21—C20—H20120.00C45—C46—H46120.00
C19—C20—H20120.00C47—C46—H46120.00
C20—C21—H21120.00C46—C47—H47120.00
C22—C21—H21120.00C48—C47—H47120.00
C21—C22—H22120.00C43—C48—H48120.00
C23—C22—H22120.00C47—C48—H48120.00
C3—N1—C1—N20.36 (17)C13—C14—C15—C161.1 (2)
C10—N1—C1—N2177.56 (14)C14—C15—C16—Cl1179.79 (12)
C3—N1—C1—C13179.04 (15)C14—C15—C16—C170.4 (2)
C10—N1—C1—C133.8 (2)C15—C16—C17—C180.4 (2)
C1—N1—C3—C4177.32 (14)Cl1—C16—C17—C18179.41 (13)
C1—N1—C10—C1191.50 (18)C16—C17—C18—C130.5 (2)
C3—N1—C10—C1185.20 (18)C2—C19—C24—C23177.66 (15)
C1—N1—C3—C20.06 (17)C20—C19—C24—C230.1 (2)
C10—N1—C3—C45.4 (2)C24—C19—C20—C210.4 (2)
C10—N1—C3—C2177.30 (14)C2—C19—C20—C21178.03 (14)
C2—N2—C1—C13179.25 (14)C19—C20—C21—C220.1 (2)
C2—N2—C1—N10.49 (17)C20—C21—C22—C230.4 (2)
C1—N2—C2—C30.45 (17)C21—C22—C23—C240.7 (2)
C1—N2—C2—C19176.82 (13)C22—C23—C24—C190.4 (2)
C25—N3—C27—C28178.62 (13)N4—C25—C37—C42136.27 (16)
C34—N3—C25—N4176.98 (13)N4—C25—C37—C3840.4 (2)
C25—N3—C34—C35104.98 (18)N3—C25—C37—C38140.18 (15)
C34—N3—C27—C284.0 (2)N3—C25—C37—C4243.2 (2)
C25—N3—C27—C260.04 (15)N4—C26—C27—N30.33 (16)
C27—N3—C25—N40.27 (16)C27—C26—C43—C4429.4 (2)
C27—N3—C25—C37179.26 (13)N4—C26—C43—C4828.1 (2)
C27—N3—C34—C3578.23 (18)C43—C26—C27—N3177.88 (14)
C34—N3—C27—C26177.43 (13)C27—C26—C43—C48149.97 (16)
C34—N3—C25—C373.5 (2)N4—C26—C27—C28178.74 (14)
C26—N4—C25—C37179.07 (13)N4—C26—C43—C44152.57 (15)
C26—N4—C25—N30.46 (16)C43—C26—C27—C280.5 (3)
C25—N4—C26—C270.49 (16)N3—C27—C28—C3374.0 (2)
C25—N4—C26—C43177.85 (13)N3—C27—C28—C29108.89 (17)
N1—C1—C13—C14139.66 (16)C26—C27—C28—C2969.3 (2)
N1—C1—C13—C1844.2 (2)C26—C27—C28—C33107.87 (19)
N2—C1—C13—C18137.26 (17)C27—C28—C29—C30177.11 (15)
N2—C1—C13—C1438.9 (2)C29—C28—C33—C320.7 (2)
C3—C2—C19—C244.5 (3)C33—C28—C29—C300.1 (2)
N2—C2—C3—N10.23 (17)C27—C28—C33—C32177.86 (15)
N2—C2—C3—C4176.54 (16)C28—C29—C30—C311.2 (3)
C3—C2—C19—C20173.05 (16)C29—C30—C31—C321.4 (3)
N2—C2—C19—C202.4 (2)C30—C31—C32—C330.6 (3)
N2—C2—C19—C24179.91 (14)C31—C32—C33—C280.5 (3)
C19—C2—C3—N1175.95 (15)N3—C34—C35—C364.3 (3)
C19—C2—C3—C40.8 (3)C25—C37—C38—C39177.66 (14)
N1—C3—C4—C965.7 (2)C42—C37—C38—C390.9 (2)
C2—C3—C4—C569.3 (2)C25—C37—C42—C41177.44 (13)
N1—C3—C4—C5114.35 (17)C38—C37—C42—C410.8 (2)
C2—C3—C4—C9110.7 (2)C37—C38—C39—C400.3 (2)
C3—C4—C9—C8179.65 (15)C38—C39—C40—Cl2179.77 (12)
C5—C4—C9—C80.4 (2)C38—C39—C40—C410.6 (2)
C9—C4—C5—C60.1 (2)Cl2—C40—C41—C42179.66 (11)
C3—C4—C5—C6179.87 (15)C39—C40—C41—C420.7 (2)
C4—C5—C6—C70.4 (2)C40—C41—C42—C370.0 (2)
C5—C6—C7—C80.3 (3)C26—C43—C44—C45178.42 (15)
C6—C7—C8—C90.2 (3)C48—C43—C44—C451.0 (2)
C7—C8—C9—C40.5 (3)C26—C43—C48—C47178.02 (15)
N1—C10—C11—C126.4 (2)C44—C43—C48—C471.4 (2)
C18—C13—C14—C151.0 (2)C43—C44—C45—C460.0 (2)
C14—C13—C18—C170.2 (2)C44—C45—C46—C470.5 (3)
C1—C13—C18—C17175.91 (15)C45—C46—C47—C480.1 (3)
C1—C13—C14—C15175.37 (15)C46—C47—C48—C430.9 (3)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg4 and Cg8 are the centroids of the C4–C9, C19–C24 and C43–C48 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C12—H12A···N10.952.552.880 (2)100
C20—H20···N20.952.442.804 (2)102
C36—H36A···N30.952.562.887 (2)100
C5—H5···Cg4i0.952.763.5968 (17)147
C11—H11···Cg8ii0.952.833.5879 (19)137
C33—H33···Cg2iii0.952.893.8217 (18)166
Symmetry codes: (i) x, y+1, z; (ii) x, y, z+1; (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC24H19ClN2
Mr370.86
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)10.0916 (7), 13.1386 (9), 15.6155 (10)
α, β, γ (°)72.924 (1), 86.849 (1), 71.830 (1)
V3)1879.0 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.57 × 0.33 × 0.28
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.919, 0.942
No. of measured, independent and
observed [I > 2σ(I)] reflections
20791, 7718, 6764
Rint0.023
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.106, 1.07
No. of reflections7718
No. of parameters487
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.23

Computer programs: SMART (Bruker, 2001), SAINT (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
Cg2, Cg4 and Cg8 are the centroids of the C4–C9, C19–C24 and C43–C48 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C5—H5···Cg4i0.952.763.5968 (17)147
C11—H11···Cg8ii0.952.833.5879 (19)137
C33—H33···Cg2iii0.952.893.8217 (18)166
Symmetry codes: (i) x, y+1, z; (ii) x, y, z+1; (iii) 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 6| June 2013| Pages o875-o876
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