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

Mohamed, S.K.; Akkurt, M.; Marzouk, A.A.E.; Santoyo-Gonzalez, F.; Elremaily, M.A.A.

doi:10.1107/S1600536813012592

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o875-o876

doi:10.1107/S1600536813012592

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

Shaaban K. Mohamed,^a,^b ^* Mehmet Akkurt,^c Adel A. E. Marzouk,^d Francisco Santoyo-Gonzalez ^e and Mahmoud A. A. Elremaily ^f

^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 π–π 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 ); 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

Crystal data

C₂₄H₁₉ClN₂
M_r = 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 ) T_min = 0.919, T_max = 0.942
20791 measured reflections
7718 independent reflections
6764 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.106
S = 1.07
7718 reflections
487 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −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	D⋯A	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 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813012592/hg5314sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012592/hg5314Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813012592/hg5314Isup3.cml

checkCIF report

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.

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

	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.
	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

C₂₄H₁₉ClN₂	Z = 4
M_r = 370.86	F(000) = 776
Triclinic, P1	D_x = 1.311 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0916 (7) Å	Cell parameters from 9362 reflections
b = 13.1386 (9) Å	θ = 4.6–55.6°
c = 15.6155 (10) Å	µ = 0.21 mm⁻¹
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 tube	6764 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
phi and ω scans	θ_max = 26.5°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −12→12
T_min = 0.919, T_max = 0.942	k = −16→16
20791 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0514P)² + 0.7786P] where P = (F_o² + 2F_c²)/3
7718 reflections	(Δ/σ)_max = 0.001
487 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₄H₁₉ClN₂	γ = 71.830 (1)°
M_r = 370.86	V = 1879.0 (2) Å³
Triclinic, P1	Z = 4
a = 10.0916 (7) Å	Mo Kα radiation
b = 13.1386 (9) Å	µ = 0.21 mm⁻¹
c = 15.6155 (10) Å	T = 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)
T_min = 0.919, T_max = 0.942	R_int = 0.023
20791 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	Δρ_max = 0.34 e Å⁻³
7718 reflections	Δρ_min = −0.23 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Cl1	−0.20646 (4)	0.09006 (3)	0.65803 (2)	0.0300 (1)
N1	−0.02163 (12)	0.17529 (10)	0.21321 (8)	0.0200 (3)
N2	0.06068 (12)	0.28573 (10)	0.26375 (8)	0.0200 (3)
C1	−0.00889 (14)	0.21232 (12)	0.28437 (10)	0.0197 (4)
C2	0.09418 (14)	0.29822 (11)	0.17502 (9)	0.0189 (4)
C3	0.04422 (14)	0.22994 (12)	0.14208 (9)	0.0196 (4)
C4	0.05483 (15)	0.20489 (12)	0.05485 (10)	0.0203 (4)
C5	−0.01427 (15)	0.28619 (12)	−0.02220 (10)	0.0218 (4)
C6	−0.00411 (15)	0.26283 (13)	−0.10377 (10)	0.0233 (4)
C7	0.07436 (16)	0.15777 (13)	−0.10974 (10)	0.0259 (4)
C8	0.14332 (17)	0.07618 (13)	−0.03361 (11)	0.0276 (4)
C9	0.13453 (16)	0.09918 (13)	0.04827 (10)	0.0249 (4)
C10	−0.09628 (16)	0.09705 (13)	0.20987 (10)	0.0238 (4)
C11	−0.24612 (17)	0.15345 (14)	0.17687 (10)	0.0277 (5)
C12	−0.30685 (17)	0.26199 (14)	0.14500 (11)	0.0301 (5)
C13	−0.06083 (15)	0.17650 (12)	0.37484 (10)	0.0202 (4)
C14	0.02610 (16)	0.16120 (12)	0.44742 (10)	0.0227 (4)
C15	−0.01711 (16)	0.13543 (12)	0.53460 (10)	0.0237 (4)
C16	−0.14858 (16)	0.12304 (12)	0.54890 (10)	0.0222 (4)
C17	−0.23644 (16)	0.13630 (13)	0.47904 (10)	0.0239 (4)
C18	−0.19289 (16)	0.16348 (13)	0.39192 (10)	0.0240 (4)
C19	0.17971 (14)	0.37187 (11)	0.13467 (10)	0.0195 (4)
C20	0.22749 (15)	0.42241 (12)	0.18880 (10)	0.0221 (4)
C21	0.31189 (16)	0.48977 (12)	0.15487 (10)	0.0238 (4)
C22	0.35045 (15)	0.50794 (12)	0.06640 (11)	0.0244 (4)
C23	0.30485 (16)	0.45768 (13)	0.01221 (10)	0.0249 (5)
C24	0.22005 (15)	0.39068 (12)	0.04585 (10)	0.0229 (4)
Cl2	−0.42972 (4)	0.65508 (3)	0.50155 (3)	0.0334 (1)
N3	0.19935 (12)	0.35109 (10)	0.73274 (8)	0.0194 (3)
N4	0.17457 (12)	0.23629 (10)	0.65869 (8)	0.0205 (3)
C25	0.11724 (15)	0.33401 (12)	0.67463 (9)	0.0201 (4)
C26	0.29983 (15)	0.18823 (12)	0.70807 (9)	0.0197 (4)
C27	0.31680 (14)	0.25751 (12)	0.75442 (9)	0.0192 (4)
C28	0.43246 (15)	0.24556 (11)	0.81453 (10)	0.0195 (4)
C29	0.56009 (16)	0.25167 (13)	0.77852 (10)	0.0236 (4)
C30	0.67230 (16)	0.23572 (13)	0.83402 (11)	0.0261 (4)
C31	0.65703 (16)	0.21555 (13)	0.92575 (11)	0.0259 (5)
C32	0.53069 (17)	0.20896 (13)	0.96205 (10)	0.0269 (4)
C33	0.41862 (16)	0.22345 (13)	0.90689 (10)	0.0239 (4)
C34	0.17099 (16)	0.44544 (13)	0.77037 (10)	0.0243 (5)
C35	0.25101 (17)	0.52512 (13)	0.72946 (12)	0.0310 (5)
C36	0.33377 (19)	0.52130 (15)	0.66240 (14)	0.0399 (6)
C37	−0.01782 (15)	0.41483 (12)	0.63418 (9)	0.0202 (4)
C38	−0.12790 (16)	0.37477 (13)	0.62550 (10)	0.0246 (4)
C39	−0.25512 (16)	0.44770 (13)	0.58485 (11)	0.0277 (5)
C40	−0.27089 (15)	0.56125 (13)	0.55261 (10)	0.0245 (4)
C41	−0.16323 (16)	0.60279 (13)	0.55934 (10)	0.0230 (4)
C42	−0.03662 (16)	0.52952 (12)	0.60013 (9)	0.0218 (4)
C43	0.39728 (15)	0.07904 (12)	0.70529 (10)	0.0202 (4)
C44	0.48893 (15)	0.00912 (12)	0.77813 (10)	0.0222 (4)
C45	0.58242 (16)	−0.09211 (13)	0.77391 (11)	0.0256 (4)
C46	0.58688 (16)	−0.12606 (13)	0.69738 (11)	0.0273 (5)
C47	0.49576 (17)	−0.05782 (13)	0.62534 (11)	0.0279 (5)
C48	0.40109 (16)	0.04347 (13)	0.62921 (10)	0.0251 (5)
H5	−0.06880	0.35820	−0.01870	0.0260*
H6	−0.05110	0.31900	−0.15580	0.0280*
H7	0.08080	0.14180	−0.16560	0.0310*
H8	0.19690	0.00410	−0.03750	0.0330*
H9	0.18270	0.04300	0.10000	0.0300*
H10A	−0.09340	0.04490	0.27070	0.0290*
H10B	−0.04730	0.05210	0.17000	0.0290*
H11	−0.30190	0.10640	0.17930	0.0330*
H12A	−0.25510	0.31230	0.14130	0.0360*
H12B	−0.40240	0.29010	0.12560	0.0360*
H14	0.11660	0.16870	0.43660	0.0270*
H15	0.04190	0.12650	0.58340	0.0280*
H17	−0.32590	0.12690	0.49060	0.0290*
H18	−0.25320	0.17330	0.34350	0.0290*
H20	0.20190	0.41050	0.24960	0.0260*
H21	0.34330	0.52350	0.19250	0.0290*
H22	0.40760	0.55440	0.04310	0.0290*
H23	0.33170	0.46910	−0.04830	0.0300*
H24	0.18910	0.35720	0.00790	0.0270*
H29	0.57050	0.26690	0.71560	0.0280*
H30	0.75960	0.23860	0.80910	0.0310*
H31	0.73310	0.20630	0.96360	0.0310*
H32	0.52050	0.19450	1.02490	0.0320*
H33	0.33240	0.21830	0.93230	0.0290*
H34A	0.19370	0.41560	0.83560	0.0290*
H34B	0.07000	0.48710	0.76200	0.0290*
H35	0.24060	0.58450	0.75480	0.0370*
H36A	0.34770	0.46350	0.63470	0.0480*
H36B	0.38000	0.57630	0.64130	0.0480*
H38	−0.11570	0.29680	0.64760	0.0290*
H39	−0.32990	0.42020	0.57930	0.0330*
H41	−0.17570	0.68070	0.53630	0.0280*
H42	0.03790	0.55760	0.60490	0.0260*
H44	0.48700	0.03130	0.83100	0.0270*
H45	0.64390	−0.13850	0.82380	0.0310*
H46	0.65140	−0.19510	0.69440	0.0330*
H47	0.49800	−0.08050	0.57270	0.0330*
H48	0.33850	0.08880	0.57960	0.0300*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0315 (2)	0.0358 (2)	0.0215 (2)	−0.0115 (2)	0.0067 (2)	−0.0067 (2)
N1	0.0199 (6)	0.0201 (6)	0.0199 (6)	−0.0079 (5)	−0.0001 (5)	−0.0038 (5)
N2	0.0186 (6)	0.0195 (6)	0.0207 (6)	−0.0055 (5)	0.0020 (5)	−0.0047 (5)
C1	0.0172 (7)	0.0189 (7)	0.0215 (7)	−0.0042 (5)	−0.0004 (5)	−0.0049 (5)
C2	0.0163 (7)	0.0181 (7)	0.0197 (7)	−0.0028 (5)	0.0002 (5)	−0.0044 (5)
C3	0.0173 (7)	0.0189 (7)	0.0201 (7)	−0.0046 (5)	0.0006 (5)	−0.0030 (5)
C4	0.0191 (7)	0.0225 (7)	0.0220 (7)	−0.0102 (6)	0.0018 (5)	−0.0066 (6)
C5	0.0182 (7)	0.0224 (7)	0.0259 (8)	−0.0078 (6)	0.0016 (6)	−0.0074 (6)
C6	0.0204 (7)	0.0293 (8)	0.0210 (7)	−0.0116 (6)	−0.0003 (6)	−0.0041 (6)
C7	0.0292 (8)	0.0322 (8)	0.0227 (7)	−0.0158 (7)	0.0046 (6)	−0.0113 (6)
C8	0.0313 (8)	0.0221 (7)	0.0312 (8)	−0.0082 (6)	0.0049 (7)	−0.0110 (6)
C9	0.0275 (8)	0.0211 (7)	0.0247 (8)	−0.0076 (6)	0.0003 (6)	−0.0043 (6)
C10	0.0278 (8)	0.0232 (7)	0.0236 (7)	−0.0133 (6)	0.0010 (6)	−0.0058 (6)
C11	0.0285 (8)	0.0352 (9)	0.0242 (8)	−0.0179 (7)	−0.0012 (6)	−0.0067 (7)
C12	0.0266 (8)	0.0364 (9)	0.0278 (8)	−0.0096 (7)	−0.0040 (6)	−0.0094 (7)
C13	0.0221 (7)	0.0173 (7)	0.0212 (7)	−0.0064 (6)	0.0014 (6)	−0.0052 (5)
C14	0.0217 (7)	0.0219 (7)	0.0257 (8)	−0.0087 (6)	0.0012 (6)	−0.0065 (6)
C15	0.0258 (8)	0.0238 (7)	0.0226 (7)	−0.0086 (6)	−0.0008 (6)	−0.0072 (6)
C16	0.0270 (8)	0.0191 (7)	0.0198 (7)	−0.0073 (6)	0.0047 (6)	−0.0051 (6)
C17	0.0201 (7)	0.0257 (8)	0.0263 (8)	−0.0087 (6)	0.0038 (6)	−0.0071 (6)
C18	0.0223 (7)	0.0248 (7)	0.0243 (8)	−0.0076 (6)	−0.0017 (6)	−0.0055 (6)
C19	0.0161 (7)	0.0159 (6)	0.0239 (7)	−0.0028 (5)	0.0006 (5)	−0.0044 (5)
C20	0.0212 (7)	0.0217 (7)	0.0227 (7)	−0.0058 (6)	0.0019 (6)	−0.0065 (6)
C21	0.0225 (7)	0.0215 (7)	0.0293 (8)	−0.0072 (6)	−0.0013 (6)	−0.0093 (6)
C22	0.0195 (7)	0.0216 (7)	0.0318 (8)	−0.0092 (6)	0.0037 (6)	−0.0048 (6)
C23	0.0244 (8)	0.0258 (8)	0.0240 (8)	−0.0089 (6)	0.0048 (6)	−0.0059 (6)
C24	0.0240 (8)	0.0229 (7)	0.0232 (7)	−0.0088 (6)	0.0012 (6)	−0.0074 (6)
Cl2	0.0213 (2)	0.0305 (2)	0.0393 (2)	−0.0009 (2)	−0.0062 (2)	−0.0029 (2)
N3	0.0187 (6)	0.0195 (6)	0.0189 (6)	−0.0043 (5)	−0.0008 (5)	−0.0054 (5)
N4	0.0191 (6)	0.0219 (6)	0.0190 (6)	−0.0057 (5)	−0.0006 (5)	−0.0043 (5)
C25	0.0199 (7)	0.0224 (7)	0.0183 (7)	−0.0074 (6)	0.0015 (5)	−0.0056 (6)
C26	0.0192 (7)	0.0203 (7)	0.0176 (7)	−0.0057 (6)	0.0002 (5)	−0.0029 (5)
C27	0.0174 (7)	0.0200 (7)	0.0188 (7)	−0.0053 (5)	0.0012 (5)	−0.0040 (5)
C28	0.0198 (7)	0.0163 (7)	0.0229 (7)	−0.0050 (5)	−0.0019 (5)	−0.0064 (5)
C29	0.0238 (8)	0.0247 (7)	0.0221 (7)	−0.0078 (6)	0.0010 (6)	−0.0062 (6)
C30	0.0210 (7)	0.0277 (8)	0.0311 (8)	−0.0094 (6)	0.0006 (6)	−0.0087 (6)
C31	0.0248 (8)	0.0238 (8)	0.0292 (8)	−0.0074 (6)	−0.0069 (6)	−0.0066 (6)
C32	0.0305 (8)	0.0304 (8)	0.0210 (7)	−0.0111 (7)	−0.0013 (6)	−0.0070 (6)
C33	0.0229 (8)	0.0264 (8)	0.0235 (7)	−0.0085 (6)	0.0022 (6)	−0.0084 (6)
C34	0.0230 (8)	0.0249 (8)	0.0253 (8)	−0.0040 (6)	−0.0018 (6)	−0.0110 (6)
C35	0.0282 (8)	0.0216 (8)	0.0436 (10)	−0.0056 (6)	−0.0063 (7)	−0.0110 (7)
C36	0.0366 (10)	0.0293 (9)	0.0537 (12)	−0.0145 (8)	0.0069 (8)	−0.0083 (8)
C37	0.0198 (7)	0.0236 (7)	0.0163 (7)	−0.0041 (6)	0.0005 (5)	−0.0071 (6)
C38	0.0249 (8)	0.0218 (7)	0.0254 (8)	−0.0066 (6)	0.0000 (6)	−0.0050 (6)
C39	0.0204 (8)	0.0299 (8)	0.0320 (8)	−0.0090 (6)	−0.0023 (6)	−0.0058 (7)
C40	0.0192 (7)	0.0266 (8)	0.0227 (7)	−0.0016 (6)	−0.0013 (6)	−0.0054 (6)
C41	0.0254 (8)	0.0206 (7)	0.0207 (7)	−0.0044 (6)	0.0002 (6)	−0.0055 (6)
C42	0.0228 (7)	0.0244 (7)	0.0197 (7)	−0.0078 (6)	0.0007 (6)	−0.0079 (6)
C43	0.0178 (7)	0.0198 (7)	0.0243 (7)	−0.0080 (6)	0.0014 (6)	−0.0060 (6)
C44	0.0212 (7)	0.0222 (7)	0.0241 (7)	−0.0091 (6)	0.0001 (6)	−0.0053 (6)
C45	0.0203 (7)	0.0231 (7)	0.0303 (8)	−0.0057 (6)	−0.0029 (6)	−0.0038 (6)
C46	0.0218 (8)	0.0217 (7)	0.0380 (9)	−0.0042 (6)	0.0010 (6)	−0.0107 (7)
C47	0.0270 (8)	0.0283 (8)	0.0322 (8)	−0.0075 (7)	0.0004 (6)	−0.0154 (7)
C48	0.0240 (8)	0.0244 (8)	0.0257 (8)	−0.0054 (6)	−0.0039 (6)	−0.0068 (6)

Geometric parameters (Å, º) top

Cl1—C16	1.7458 (16)	C18—H18	0.9500
Cl2—C40	1.7480 (17)	C20—H20	0.9500
N1—C1	1.364 (2)	C21—H21	0.9500
N1—C3	1.3925 (19)	C22—H22	0.9500
N1—C10	1.465 (2)	C23—H23	0.9500
N2—C2	1.3822 (18)	C24—H24	0.9500
N2—C1	1.320 (2)	C25—C37	1.477 (2)
N3—C34	1.467 (2)	C26—C27	1.371 (2)
N3—C27	1.386 (2)	C26—C43	1.476 (2)
N3—C25	1.3706 (19)	C27—C28	1.479 (2)
N4—C25	1.324 (2)	C28—C29	1.393 (2)
N4—C26	1.384 (2)	C28—C33	1.393 (2)
C1—C13	1.475 (2)	C29—C30	1.389 (2)
C2—C19	1.477 (2)	C30—C31	1.387 (2)
C2—C3	1.380 (2)	C31—C32	1.384 (2)
C3—C4	1.483 (2)	C32—C33	1.391 (2)
C4—C5	1.396 (2)	C34—C35	1.495 (2)
C4—C9	1.402 (2)	C35—C36	1.306 (3)
C5—C6	1.387 (2)	C37—C38	1.397 (2)
C6—C7	1.388 (2)	C37—C42	1.397 (2)
C7—C8	1.387 (2)	C38—C39	1.391 (2)
C8—C9	1.390 (2)	C39—C40	1.387 (2)
C10—C11	1.505 (2)	C40—C41	1.380 (2)
C11—C12	1.315 (3)	C41—C42	1.388 (2)
C13—C14	1.400 (2)	C43—C44	1.402 (2)
C13—C18	1.397 (2)	C43—C48	1.393 (2)
C14—C15	1.384 (2)	C44—C45	1.388 (2)
C15—C16	1.385 (2)	C45—C46	1.387 (2)
C16—C17	1.380 (2)	C46—C47	1.386 (2)
C17—C18	1.385 (2)	C47—C48	1.391 (2)
C19—C20	1.401 (2)	C29—H29	0.9500
C19—C24	1.396 (2)	C30—H30	0.9500
C20—C21	1.391 (2)	C31—H31	0.9500
C21—C22	1.386 (2)	C32—H32	0.9500
C22—C23	1.387 (2)	C33—H33	0.9500
C23—C24	1.390 (2)	C34—H34A	0.9900
C5—H5	0.9500	C34—H34B	0.9900
C6—H6	0.9500	C35—H35	0.9500
C7—H7	0.9500	C36—H36A	0.9500
C8—H8	0.9500	C36—H36B	0.9500
C9—H9	0.9500	C38—H38	0.9500
C10—H10A	0.9900	C39—H39	0.9500
C10—H10B	0.9900	C41—H41	0.9500
C11—H11	0.9500	C42—H42	0.9500
C12—H12B	0.9500	C44—H44	0.9500
C12—H12A	0.9500	C45—H45	0.9500
C14—H14	0.9500	C46—H46	0.9500
C15—H15	0.9500	C47—H47	0.9500
C17—H17	0.9500	C48—H48	0.9500

C1—N1—C3	107.20 (12)	C24—C23—H23	120.00
C1—N1—C10	126.91 (12)	C22—C23—H23	120.00
C3—N1—C10	125.83 (12)	C19—C24—H24	120.00
C1—N2—C2	106.30 (12)	C23—C24—H24	120.00
C27—N3—C34	124.52 (12)	N3—C25—N4	111.56 (13)
C25—N3—C27	106.76 (12)	N3—C25—C37	124.29 (14)
C25—N3—C34	128.66 (13)	N4—C25—C37	124.15 (13)
C25—N4—C26	105.60 (12)	N4—C26—C27	110.18 (13)
N1—C1—C13	126.68 (14)	N4—C26—C43	121.86 (13)
N2—C1—C13	121.93 (14)	C27—C26—C43	127.93 (14)
N1—C1—N2	111.38 (13)	N3—C27—C26	105.91 (13)
N2—C2—C3	109.72 (12)	N3—C27—C28	123.01 (13)
N2—C2—C19	118.31 (13)	C26—C27—C28	131.07 (14)
C3—C2—C19	131.84 (13)	C27—C28—C29	119.28 (13)
N1—C3—C2	105.40 (12)	C27—C28—C33	121.48 (14)
N1—C3—C4	121.12 (13)	C29—C28—C33	119.18 (14)
C2—C3—C4	133.41 (13)	C28—C29—C30	120.42 (14)
C3—C4—C9	120.62 (13)	C29—C30—C31	120.05 (15)
C5—C4—C9	118.78 (14)	C30—C31—C32	119.84 (15)
C3—C4—C5	120.61 (14)	C31—C32—C33	120.30 (14)
C4—C5—C6	120.60 (15)	C28—C33—C32	120.20 (15)
C5—C6—C7	120.34 (14)	N3—C34—C35	114.07 (13)
C6—C7—C8	119.61 (14)	C34—C35—C36	126.56 (17)
C7—C8—C9	120.41 (16)	C25—C37—C38	119.00 (14)
C4—C9—C8	120.26 (15)	C25—C37—C42	121.96 (14)
N1—C10—C11	113.67 (14)	C38—C37—C42	118.96 (14)
C10—C11—C12	125.92 (17)	C37—C38—C39	120.79 (15)
C1—C13—C18	124.28 (14)	C38—C39—C40	118.82 (15)
C14—C13—C18	118.67 (14)	Cl2—C40—C39	119.90 (13)
C1—C13—C14	116.95 (14)	Cl2—C40—C41	118.58 (13)
C13—C14—C15	121.38 (15)	C39—C40—C41	121.53 (15)
C14—C15—C16	118.29 (15)	C40—C41—C42	119.34 (15)
Cl1—C16—C15	119.59 (12)	C37—C42—C41	120.57 (15)
C15—C16—C17	121.89 (14)	C26—C43—C44	121.28 (13)
Cl1—C16—C17	118.52 (13)	C26—C43—C48	120.42 (14)
C16—C17—C18	119.38 (15)	C44—C43—C48	118.30 (14)
C13—C18—C17	120.39 (15)	C43—C44—C45	120.76 (14)
C20—C19—C24	117.97 (14)	C44—C45—C46	120.53 (15)
C2—C19—C20	118.62 (13)	C45—C46—C47	119.06 (16)
C2—C19—C24	123.36 (13)	C46—C47—C48	120.79 (15)
C19—C20—C21	120.95 (14)	C43—C48—C47	120.55 (15)
C20—C21—C22	120.31 (14)	C28—C29—H29	120.00
C21—C22—C23	119.37 (15)	C30—C29—H29	120.00
C22—C23—C24	120.43 (14)	C29—C30—H30	120.00
C19—C24—C23	120.96 (14)	C31—C30—H30	120.00
C4—C5—H5	120.00	C30—C31—H31	120.00
C6—C5—H5	120.00	C32—C31—H31	120.00
C5—C6—H6	120.00	C31—C32—H32	120.00
C7—C6—H6	120.00	C33—C32—H32	120.00
C8—C7—H7	120.00	C28—C33—H33	120.00
C6—C7—H7	120.00	C32—C33—H33	120.00
C7—C8—H8	120.00	N3—C34—H34A	109.00
C9—C8—H8	120.00	N3—C34—H34B	109.00
C8—C9—H9	120.00	C35—C34—H34A	109.00
C4—C9—H9	120.00	C35—C34—H34B	109.00
C11—C10—H10A	109.00	H34A—C34—H34B	108.00
N1—C10—H10B	109.00	C34—C35—H35	117.00
C11—C10—H10B	109.00	C36—C35—H35	117.00
H10A—C10—H10B	108.00	C35—C36—H36A	120.00
N1—C10—H10A	109.00	C35—C36—H36B	120.00
C10—C11—H11	117.00	H36A—C36—H36B	120.00
C12—C11—H11	117.00	C37—C38—H38	120.00
C11—C12—H12A	120.00	C39—C38—H38	120.00
C11—C12—H12B	120.00	C38—C39—H39	121.00
H12A—C12—H12B	120.00	C40—C39—H39	121.00
C15—C14—H14	119.00	C40—C41—H41	120.00
C13—C14—H14	119.00	C42—C41—H41	120.00
C14—C15—H15	121.00	C37—C42—H42	120.00
C16—C15—H15	121.00	C41—C42—H42	120.00
C18—C17—H17	120.00	C43—C44—H44	120.00
C16—C17—H17	120.00	C45—C44—H44	120.00
C17—C18—H18	120.00	C44—C45—H45	120.00
C13—C18—H18	120.00	C46—C45—H45	120.00
C21—C20—H20	120.00	C45—C46—H46	120.00
C19—C20—H20	120.00	C47—C46—H46	120.00
C20—C21—H21	120.00	C46—C47—H47	120.00
C22—C21—H21	120.00	C48—C47—H47	120.00
C21—C22—H22	120.00	C43—C48—H48	120.00
C23—C22—H22	120.00	C47—C48—H48	120.00

C3—N1—C1—N2	−0.36 (17)	C13—C14—C15—C16	1.1 (2)
C10—N1—C1—N2	−177.56 (14)	C14—C15—C16—Cl1	179.79 (12)
C3—N1—C1—C13	−179.04 (15)	C14—C15—C16—C17	−0.4 (2)
C10—N1—C1—C13	3.8 (2)	C15—C16—C17—C18	−0.4 (2)
C1—N1—C3—C4	177.32 (14)	Cl1—C16—C17—C18	179.41 (13)
C1—N1—C10—C11	91.50 (18)	C16—C17—C18—C13	0.5 (2)
C3—N1—C10—C11	−85.20 (18)	C2—C19—C24—C23	−177.66 (15)
C1—N1—C3—C2	0.06 (17)	C20—C19—C24—C23	−0.1 (2)
C10—N1—C3—C4	−5.4 (2)	C24—C19—C20—C21	0.4 (2)
C10—N1—C3—C2	177.30 (14)	C2—C19—C20—C21	178.03 (14)
C2—N2—C1—C13	179.25 (14)	C19—C20—C21—C22	−0.1 (2)
C2—N2—C1—N1	0.49 (17)	C20—C21—C22—C23	−0.4 (2)
C1—N2—C2—C3	−0.45 (17)	C21—C22—C23—C24	0.7 (2)
C1—N2—C2—C19	−176.82 (13)	C22—C23—C24—C19	−0.4 (2)
C25—N3—C27—C28	178.62 (13)	N4—C25—C37—C42	−136.27 (16)
C34—N3—C25—N4	−176.98 (13)	N4—C25—C37—C38	40.4 (2)
C25—N3—C34—C35	−104.98 (18)	N3—C25—C37—C38	−140.18 (15)
C34—N3—C27—C28	−4.0 (2)	N3—C25—C37—C42	43.2 (2)
C25—N3—C27—C26	0.04 (15)	N4—C26—C27—N3	−0.33 (16)
C27—N3—C25—N4	0.27 (16)	C27—C26—C43—C44	29.4 (2)
C27—N3—C25—C37	−179.26 (13)	N4—C26—C43—C48	28.1 (2)
C27—N3—C34—C35	78.23 (18)	C43—C26—C27—N3	177.88 (14)
C34—N3—C27—C26	177.43 (13)	C27—C26—C43—C48	−149.97 (16)
C34—N3—C25—C37	3.5 (2)	N4—C26—C27—C28	−178.74 (14)
C26—N4—C25—C37	179.07 (13)	N4—C26—C43—C44	−152.57 (15)
C26—N4—C25—N3	−0.46 (16)	C43—C26—C27—C28	−0.5 (3)
C25—N4—C26—C27	0.49 (16)	N3—C27—C28—C33	74.0 (2)
C25—N4—C26—C43	−177.85 (13)	N3—C27—C28—C29	−108.89 (17)
N1—C1—C13—C14	139.66 (16)	C26—C27—C28—C29	69.3 (2)
N1—C1—C13—C18	−44.2 (2)	C26—C27—C28—C33	−107.87 (19)
N2—C1—C13—C18	137.26 (17)	C27—C28—C29—C30	−177.11 (15)
N2—C1—C13—C14	−38.9 (2)	C29—C28—C33—C32	0.7 (2)
C3—C2—C19—C24	4.5 (3)	C33—C28—C29—C30	0.1 (2)
N2—C2—C3—N1	0.23 (17)	C27—C28—C33—C32	177.86 (15)
N2—C2—C3—C4	−176.54 (16)	C28—C29—C30—C31	−1.2 (3)
C3—C2—C19—C20	−173.05 (16)	C29—C30—C31—C32	1.4 (3)
N2—C2—C19—C20	2.4 (2)	C30—C31—C32—C33	−0.6 (3)
N2—C2—C19—C24	179.91 (14)	C31—C32—C33—C28	−0.5 (3)
C19—C2—C3—N1	175.95 (15)	N3—C34—C35—C36	4.3 (3)
C19—C2—C3—C4	−0.8 (3)	C25—C37—C38—C39	−177.66 (14)
N1—C3—C4—C9	−65.7 (2)	C42—C37—C38—C39	−0.9 (2)
C2—C3—C4—C5	−69.3 (2)	C25—C37—C42—C41	177.44 (13)
N1—C3—C4—C5	114.35 (17)	C38—C37—C42—C41	0.8 (2)
C2—C3—C4—C9	110.7 (2)	C37—C38—C39—C40	0.3 (2)
C3—C4—C9—C8	179.65 (15)	C38—C39—C40—Cl2	−179.77 (12)
C5—C4—C9—C8	−0.4 (2)	C38—C39—C40—C41	0.6 (2)
C9—C4—C5—C6	−0.1 (2)	Cl2—C40—C41—C42	179.66 (11)
C3—C4—C5—C6	179.87 (15)	C39—C40—C41—C42	−0.7 (2)
C4—C5—C6—C7	0.4 (2)	C40—C41—C42—C37	0.0 (2)
C5—C6—C7—C8	−0.3 (3)	C26—C43—C44—C45	−178.42 (15)
C6—C7—C8—C9	−0.2 (3)	C48—C43—C44—C45	1.0 (2)
C7—C8—C9—C4	0.5 (3)	C26—C43—C48—C47	178.02 (15)
N1—C10—C11—C12	6.4 (2)	C44—C43—C48—C47	−1.4 (2)
C18—C13—C14—C15	−1.0 (2)	C43—C44—C45—C46	0.0 (2)
C14—C13—C18—C17	0.2 (2)	C44—C45—C46—C47	−0.5 (3)
C1—C13—C18—C17	−175.91 (15)	C45—C46—C47—C48	0.1 (3)
C1—C13—C14—C15	175.37 (15)	C46—C47—C48—C43	0.9 (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···A	D—H	H···A	D···A	D—H···A
C12—H12A···N1	0.95	2.55	2.880 (2)	100
C20—H20···N2	0.95	2.44	2.804 (2)	102
C36—H36A···N3	0.95	2.56	2.887 (2)	100
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.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₉ClN₂
M_r	370.86
Crystal system, space group	Triclinic, 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)
V (Å³)	1879.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.57 × 0.33 × 0.28

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.919, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	20791, 7718, 6764
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.106, 1.07
No. of reflections	7718
No. of parameters	487
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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.

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.

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Volume 69| Part 6| June 2013| Pages o875-o876

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