Bis(1-benzyl-1H-benzimidazole-κN3)di­chlorido­zinc

Bouhfid, R.; Essassi, E.M.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536814002840

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages m94-m95

doi:10.1107/S1600536814002840

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Bis(1-benzyl-1H-benzimidazole-κN³)dichloridozinc

Rachid Bouhfid,^a El Mokhtar Essassi,^b,^a ^* Mohamed Saadi ^c and Lahcen El Ammari ^c

^aCentre Composites Nanocomposites, Moroccan Foundation for Advanced Science, Innovation and Research (MAScIR), Rabat Design Center, Rue Mohamed Al Jazouli-Madinat Al Irfane, Rabat 10100, Morocco, ^bLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco, and ^cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: em_essassi@yahoo.fr

(Received 6 February 2014; accepted 7 February 2014; online 12 February 2014)

In the title compound, [ZnCl₂(C₁₄H₁₂N₂)₂], the Zn^II atom exhibits a distorted tetrahedral coordination geometry involving two chloride anions and two N-atom donors from 1-benzyl-1H-benzimidazole ligands. In both ligands, the benzyl and benzimidazole rings are nearly perpendicular [dihedral angles = 81.7 (2) and 81.5 (2)°]. The two benzimidazole systems are essentially planar [maximum deviations = 0.015 (3) and 0.020 (2) Å] and form a dihedral angle of 78.09 (8)°. In the crystal, centrosymmetrically related molecules are linked by pairs of C—H⋯Cl hydrogen bonds into chains parallel to the a axis.

CCDC reference: 985748

Related literature

For background to the biochemical properties of benzimidazole derivatives, see: Mann et al. (2001 ); Naithani et al. (1990 ); Goudgaon et al. (2004 ). For the structures of related compounds see: Abdel-Ghani & Mansour (2011 , 2012 ); Ahuja & Prasad (1976 ).

Experimental

Crystal data

[ZnCl₂(C₁₄H₁₂N₂)₂]
M_r = 552.78
Triclinic, $[P \overline 1]$
a = 9.9819 (4) Å
b = 10.0564 (4) Å
c = 13.6641 (6) Å
α = 99.539 (2)°
β = 92.087 (2)°
γ = 99.122 (2)°
V = 1332.79 (10) Å³
Z = 2
Mo Kα radiation
μ = 1.15 mm⁻¹
T = 296 K
0.37 × 0.32 × 0.26 mm

Data collection

Bruker X8 APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.682, T_max = 0.840
30968 measured reflections
7403 independent reflections
5928 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108
S = 1.06
7403 reflections
318 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cl1ⁱ	0.93	2.81	3.660 (2)	153
C28—H28⋯Cl1ⁱⁱ	0.93	2.80	3.502 (2)	133
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 985748

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814002840/rz5104sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814002840/rz5104Isup2.hkl

checkCIF report

Comment top

Benzimidazole derivatives are important pharmacophores in drug discovery, possessing pharmacological properties including antitumor (Mann et al., 2001), anti-Parkinson (Naithani et al., 1990) and antimicrobial (Goudgaon et al., 2004) activities. A considerable number of metal benzimidazole complexes including Cr, Mn, Fe, Co, Ni, Zn, Pd, Pt, Au, and Re has been reported (Abdel-Ghani & Mansour, 2011, 2012). Metal complexes of biologically important ligands were sometimes more effective than the free ligands (Ahuja & Prasad, 1976).

The crystal structure of the title compound, show that the Zn^II ion adopts a distorted tetrahedral coordination arising from two N-atom donors from organic ligands and a two Cl^- anions (Fig. 1). The fused five- and six-membered rings are nearly coplanar with dihedral angles between them of 1.0 (2)° and 1.6 (2)° respectively. The dihedral angle between the two benzimidazole systems is of 78.09 (8)°. Each benzyl ring (C1–C6 and C15–C20) is virtually perpendicular to the benzimidazole system belonging to the same molecule (N1/N2/C8–C14 and N3/N4/C22–C28) as indicated by the dihedral angles between them of 81.7 (2)° and 81.5 (2)°, respectively. In the crystal, centrosymmetrically-related molecules are linked by C—H···Cl hydrogen bonds (Table 1) into chains running parallel to the a axis.

Related literature top

For background to the biochemical properties of benzimidazole derivatives, see: Mann et al. (2001); Naithani et al. (1990); Goudgaon et al. (2004). For the structures of related compounds see: Abdel-Ghani & Mansour (2011, 2012); Ahuja & Prasad (1976).

Experimental top

The title compound was prepared by the reaction of ZnCl₂ (164 mg, 1.2 mmol) in water (10 ml) and 1-benzyl-1H-benzimidazole (500 mg, 2.4 mmol) in ethanol (10 ml). The mixture was stirred for 12 h, filtered and set aside to crystallize at ambient temperature for several days, giving colourless single crystals on slow evaporation of the solvent.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles.

Bis(1-benzyl-1H-benzimidazole-κN³)dichloridozinc top

Crystal data top

[ZnCl₂(C₁₄H₁₂N₂)₂]	V = 1332.79 (10) Å³
M_r = 552.78	Z = 2
Triclinic, P1	F(000) = 568
Hall symbol: -p 1	D_x = 1.377 Mg m⁻³
a = 9.9819 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0564 (4) Å	µ = 1.15 mm⁻¹
c = 13.6641 (6) Å	T = 296 K
α = 99.539 (2)°	Block, colourless
β = 92.087 (2)°	0.37 × 0.32 × 0.26 mm
γ = 99.122 (2)°

Data collection top

Bruker X8 APEX diffractometer	7403 independent reflections
Radiation source: fine-focus sealed tube	5928 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 29.6°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.682, T_max = 0.840	k = −13→13
30968 measured reflections	l = −18→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0551P)² + 0.3641P] where P = (F_o² + 2F_c²)/3
7403 reflections	(Δ/σ)_max < 0.001
318 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[ZnCl₂(C₁₄H₁₂N₂)₂]	γ = 99.122 (2)°
M_r = 552.78	V = 1332.79 (10) Å³
Triclinic, P1	Z = 2
a = 9.9819 (4) Å	Mo Kα radiation
b = 10.0564 (4) Å	µ = 1.15 mm⁻¹
c = 13.6641 (6) Å	T = 296 K
α = 99.539 (2)°	0.37 × 0.32 × 0.26 mm
β = 92.087 (2)°

Data collection top

Bruker X8 APEX diffractometer	7403 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5928 reflections with I > 2σ(I)
T_min = 0.682, T_max = 0.840	R_int = 0.026
30968 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.06	Δρ_max = 0.58 e Å⁻³
7403 reflections	Δρ_min = −0.24 e Å⁻³
318 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against all reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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
C1	0.7633 (4)	0.8525 (3)	0.4366 (3)	0.1008 (11)
H1	0.7791	0.9301	0.4072	0.121*
C2	0.8206 (5)	0.8556 (4)	0.5311 (3)	0.1210 (14)
H2	0.8754	0.9350	0.5641	0.145*
C3	0.7979 (4)	0.7450 (5)	0.5757 (2)	0.1088 (13)
H3	0.8379	0.7477	0.6387	0.131*
C4	0.7162 (4)	0.6296 (4)	0.5281 (3)	0.1052 (12)
H4	0.6985	0.5537	0.5593	0.126*
C5	0.6591 (4)	0.6246 (3)	0.4331 (2)	0.0826 (8)
H5	0.6036	0.5451	0.4010	0.099*
C6	0.6835 (2)	0.7356 (2)	0.38635 (17)	0.0602 (5)
C7	0.6298 (3)	0.7325 (3)	0.28114 (18)	0.0675 (6)
H7A	0.6199	0.8247	0.2733	0.085 (9)*
H7B	0.6962	0.7031	0.2359	0.084 (9)*
C8	0.3754 (2)	0.6587 (2)	0.29074 (15)	0.0539 (5)
C9	0.3381 (3)	0.7496 (3)	0.36933 (17)	0.0692 (6)
H9	0.4018	0.8181	0.4071	0.083*
C10	0.2033 (4)	0.7334 (3)	0.3883 (2)	0.0799 (8)
H10	0.1754	0.7914	0.4411	0.096*
C11	0.1069 (3)	0.6330 (3)	0.3312 (2)	0.0775 (7)
H11	0.0163	0.6255	0.3465	0.093*
C12	0.1428 (3)	0.5448 (3)	0.25247 (19)	0.0644 (6)
H12	0.0780	0.4784	0.2138	0.077*
C13	0.2792 (2)	0.5583 (2)	0.23266 (15)	0.0510 (4)
C14	0.4755 (2)	0.5385 (2)	0.17551 (15)	0.0538 (5)
H14	0.5432	0.5085	0.1369	0.065*
C15	−0.2428 (3)	0.2655 (3)	0.2558 (2)	0.0821 (8)
H15	−0.1617	0.3181	0.2437	0.099*
C16	−0.2920 (5)	0.2837 (4)	0.3495 (2)	0.1078 (12)
H16	−0.2421	0.3458	0.4010	0.129*
C17	−0.4137 (4)	0.2106 (5)	0.3665 (2)	0.1047 (13)
H17	−0.4492	0.2271	0.4285	0.126*
C18	−0.4834 (3)	0.1131 (4)	0.2925 (2)	0.0917 (10)
H18	−0.5648	0.0613	0.3049	0.110*
C19	−0.4329 (2)	0.0915 (3)	0.19898 (18)	0.0638 (6)
H19	−0.4797	0.0243	0.1490	0.077*
C20	−0.3139 (2)	0.1694 (2)	0.18024 (15)	0.0487 (4)
C21	−0.26224 (18)	0.1483 (2)	0.07709 (15)	0.0491 (4)
H21A	−0.3058	0.0600	0.0407	0.059*
H21B	−0.2862	0.2182	0.0418	0.059*
C22	−0.04380 (18)	0.06922 (18)	0.12376 (13)	0.0409 (4)
C23	−0.0871 (2)	−0.0469 (2)	0.16412 (17)	0.0570 (5)
H23	−0.1788	−0.0802	0.1678	0.068*
C24	0.0132 (3)	−0.1098 (2)	0.1982 (2)	0.0688 (6)
H24	−0.0113	−0.1878	0.2261	0.083*
C25	0.1510 (3)	−0.0600 (2)	0.19231 (18)	0.0638 (6)
H25	0.2157	−0.1056	0.2166	0.077*
C26	0.1940 (2)	0.0551 (2)	0.15140 (15)	0.0510 (4)
H26	0.2858	0.0878	0.1472	0.061*
C27	0.09351 (18)	0.11926 (18)	0.11694 (12)	0.0393 (3)
C28	−0.02314 (18)	0.24853 (19)	0.05074 (14)	0.0447 (4)
H28	−0.0461	0.3176	0.0191	0.054*
N1	0.49942 (19)	0.6426 (2)	0.25291 (13)	0.0562 (4)
N2	0.34613 (17)	0.48349 (18)	0.16007 (13)	0.0515 (4)
N3	0.10356 (15)	0.23339 (16)	0.07047 (12)	0.0443 (3)
N4	−0.11488 (15)	0.15456 (16)	0.08096 (12)	0.0425 (3)
Zn1	0.26873 (2)	0.35268 (2)	0.034848 (16)	0.04370 (8)
Cl1	0.18906 (5)	0.46699 (5)	−0.07679 (4)	0.05779 (14)
Cl2	0.43183 (5)	0.23659 (6)	−0.01957 (4)	0.05514 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.128 (3)	0.0754 (18)	0.082 (2)	−0.0178 (19)	−0.027 (2)	0.0067 (16)
C2	0.147 (4)	0.105 (3)	0.085 (2)	−0.009 (2)	−0.049 (2)	−0.015 (2)
C3	0.131 (3)	0.130 (3)	0.0621 (17)	0.044 (3)	−0.0313 (19)	−0.005 (2)
C4	0.139 (3)	0.101 (2)	0.081 (2)	0.032 (2)	−0.024 (2)	0.0289 (19)
C5	0.105 (2)	0.0691 (16)	0.0702 (16)	0.0086 (15)	−0.0213 (15)	0.0133 (13)
C6	0.0603 (13)	0.0638 (13)	0.0514 (11)	0.0031 (10)	−0.0037 (10)	0.0035 (10)
C7	0.0673 (14)	0.0725 (15)	0.0551 (12)	−0.0147 (12)	−0.0033 (11)	0.0164 (11)
C8	0.0656 (13)	0.0573 (11)	0.0423 (10)	0.0116 (10)	−0.0011 (9)	0.0186 (8)
C9	0.0940 (19)	0.0659 (14)	0.0497 (12)	0.0184 (13)	−0.0031 (12)	0.0124 (10)
C10	0.107 (2)	0.0841 (18)	0.0608 (14)	0.0472 (17)	0.0141 (15)	0.0157 (13)
C11	0.0728 (16)	0.094 (2)	0.0791 (17)	0.0406 (15)	0.0165 (14)	0.0269 (15)
C12	0.0562 (12)	0.0737 (15)	0.0688 (14)	0.0189 (11)	0.0059 (11)	0.0198 (12)
C13	0.0550 (11)	0.0539 (11)	0.0479 (10)	0.0116 (9)	0.0019 (8)	0.0177 (8)
C14	0.0516 (11)	0.0620 (12)	0.0454 (10)	−0.0021 (9)	0.0040 (8)	0.0136 (9)
C15	0.090 (2)	0.0796 (18)	0.0657 (15)	−0.0004 (15)	0.0121 (14)	−0.0051 (13)
C16	0.128 (3)	0.124 (3)	0.0638 (18)	0.033 (3)	0.0048 (19)	−0.0162 (18)
C17	0.099 (2)	0.178 (4)	0.0517 (15)	0.064 (3)	0.0180 (16)	0.0198 (19)
C18	0.0571 (15)	0.161 (3)	0.0696 (17)	0.0273 (18)	0.0195 (13)	0.045 (2)
C19	0.0406 (10)	0.0944 (17)	0.0597 (12)	0.0133 (11)	0.0059 (9)	0.0199 (12)
C20	0.0455 (10)	0.0543 (11)	0.0502 (10)	0.0158 (8)	0.0057 (8)	0.0124 (8)
C21	0.0338 (8)	0.0610 (11)	0.0525 (10)	0.0051 (8)	0.0037 (7)	0.0129 (9)
C22	0.0399 (8)	0.0422 (9)	0.0400 (8)	0.0031 (7)	−0.0006 (7)	0.0099 (7)
C23	0.0510 (11)	0.0547 (11)	0.0668 (13)	−0.0035 (9)	0.0029 (9)	0.0267 (10)
C24	0.0727 (15)	0.0575 (13)	0.0822 (16)	0.0032 (11)	−0.0030 (12)	0.0387 (12)
C25	0.0673 (14)	0.0640 (13)	0.0676 (14)	0.0189 (11)	−0.0075 (11)	0.0279 (11)
C26	0.0440 (10)	0.0595 (11)	0.0519 (10)	0.0106 (8)	−0.0034 (8)	0.0160 (9)
C27	0.0400 (8)	0.0402 (8)	0.0375 (8)	0.0043 (7)	−0.0002 (6)	0.0092 (7)
C28	0.0408 (9)	0.0429 (9)	0.0539 (10)	0.0070 (7)	0.0038 (8)	0.0182 (8)
N1	0.0570 (10)	0.0648 (11)	0.0434 (8)	−0.0043 (8)	−0.0011 (7)	0.0144 (8)
N2	0.0464 (9)	0.0572 (10)	0.0502 (9)	0.0023 (7)	0.0031 (7)	0.0129 (7)
N3	0.0377 (7)	0.0442 (8)	0.0539 (9)	0.0042 (6)	0.0031 (6)	0.0189 (7)
N4	0.0359 (7)	0.0451 (8)	0.0479 (8)	0.0051 (6)	0.0031 (6)	0.0140 (6)
Zn1	0.03618 (11)	0.04504 (13)	0.05179 (14)	0.00320 (8)	0.00320 (8)	0.01722 (9)
Cl1	0.0506 (3)	0.0594 (3)	0.0722 (3)	0.0134 (2)	0.0037 (2)	0.0330 (3)
Cl2	0.0428 (2)	0.0630 (3)	0.0643 (3)	0.0156 (2)	0.0044 (2)	0.0178 (2)

Geometric parameters (Å, º) top

C1—C6	1.373 (4)	C15—H15	0.9300
C1—C2	1.386 (5)	C16—C17	1.365 (6)
C1—H1	0.9300	C16—H16	0.9300
C2—C3	1.347 (6)	C17—C18	1.368 (5)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.359 (5)	C18—C19	1.387 (4)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.388 (4)	C19—C20	1.372 (3)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.370 (4)	C20—C21	1.512 (3)
C5—H5	0.9300	C21—N4	1.461 (2)
C6—C7	1.509 (3)	C21—H21A	0.9700
C7—N1	1.461 (3)	C21—H21B	0.9700
C7—H7A	0.9700	C22—N4	1.382 (2)
C7—H7B	0.9700	C22—C23	1.387 (3)
C8—N1	1.381 (3)	C22—C27	1.395 (2)
C8—C9	1.393 (3)	C23—C24	1.372 (3)
C8—C13	1.394 (3)	C23—H23	0.9300
C9—C10	1.369 (4)	C24—C25	1.398 (4)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.389 (4)	C25—C26	1.382 (3)
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.373 (4)	C26—C27	1.384 (3)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.387 (3)	C27—N3	1.393 (2)
C12—H12	0.9300	C28—N3	1.321 (2)
C13—N2	1.398 (3)	C28—N4	1.336 (2)
C14—N2	1.316 (3)	C28—H28	0.9300
C14—N1	1.344 (3)	N2—Zn1	2.0225 (17)
C14—H14	0.9300	N3—Zn1	2.0048 (15)
C15—C20	1.380 (3)	Zn1—Cl2	2.2292 (5)
C15—C16	1.382 (4)	Zn1—Cl1	2.2503 (5)

C6—C1—C2	120.4 (3)	C17—C18—C19	120.1 (3)
C6—C1—H1	119.8	C17—C18—H18	120.0
C2—C1—H1	119.8	C19—C18—H18	120.0
C3—C2—C1	120.9 (3)	C20—C19—C18	120.0 (3)
C3—C2—H2	119.6	C20—C19—H19	120.0
C1—C2—H2	119.6	C18—C19—H19	120.0
C2—C3—C4	119.6 (3)	C19—C20—C15	119.6 (2)
C2—C3—H3	120.2	C19—C20—C21	119.6 (2)
C4—C3—H3	120.2	C15—C20—C21	120.8 (2)
C3—C4—C5	120.2 (3)	N4—C21—C20	111.42 (16)
C3—C4—H4	119.9	N4—C21—H21A	109.3
C5—C4—H4	119.9	C20—C21—H21A	109.3
C6—C5—C4	120.7 (3)	N4—C21—H21B	109.3
C6—C5—H5	119.6	C20—C21—H21B	109.3
C4—C5—H5	119.6	H21A—C21—H21B	108.0
C5—C6—C1	118.3 (3)	N4—C22—C23	131.75 (17)
C5—C6—C7	122.6 (2)	N4—C22—C27	105.86 (15)
C1—C6—C7	119.2 (2)	C23—C22—C27	122.35 (17)
N1—C7—C6	114.19 (19)	C24—C23—C22	116.2 (2)
N1—C7—H7A	108.7	C24—C23—H23	121.9
C6—C7—H7A	108.7	C22—C23—H23	121.9
N1—C7—H7B	108.7	C23—C24—C25	121.9 (2)
C6—C7—H7B	108.7	C23—C24—H24	119.0
H7A—C7—H7B	107.6	C25—C24—H24	119.0
N1—C8—C9	132.6 (2)	C26—C25—C24	121.8 (2)
N1—C8—C13	106.03 (19)	C26—C25—H25	119.1
C9—C8—C13	121.4 (2)	C24—C25—H25	119.1
C10—C9—C8	116.9 (3)	C25—C26—C27	116.63 (19)
C10—C9—H9	121.6	C25—C26—H26	121.7
C8—C9—H9	121.6	C27—C26—H26	121.7
C9—C10—C11	122.0 (3)	C26—C27—N3	130.31 (17)
C9—C10—H10	119.0	C26—C27—C22	121.08 (17)
C11—C10—H10	119.0	N3—C27—C22	108.59 (15)
C12—C11—C10	121.3 (3)	N3—C28—N4	113.13 (16)
C12—C11—H11	119.4	N3—C28—H28	123.4
C10—C11—H11	119.4	N4—C28—H28	123.4
C11—C12—C13	117.7 (3)	C14—N1—C8	107.04 (18)
C11—C12—H12	121.2	C14—N1—C7	125.4 (2)
C13—C12—H12	121.2	C8—N1—C7	127.1 (2)
C12—C13—C8	120.7 (2)	C14—N2—C13	105.48 (18)
C12—C13—N2	130.8 (2)	C14—N2—Zn1	123.26 (15)
C8—C13—N2	108.46 (19)	C13—N2—Zn1	129.57 (14)
N2—C14—N1	113.0 (2)	C28—N3—C27	105.30 (14)
N2—C14—H14	123.5	C28—N3—Zn1	124.79 (12)
N1—C14—H14	123.5	C27—N3—Zn1	129.89 (12)
C20—C15—C16	120.0 (3)	C28—N4—C22	107.12 (15)
C20—C15—H15	120.0	C28—N4—C21	126.89 (16)
C16—C15—H15	120.0	C22—N4—C21	125.84 (15)
C17—C16—C15	120.2 (3)	N3—Zn1—N2	107.29 (7)
C17—C16—H16	119.9	N3—Zn1—Cl2	113.31 (5)
C15—C16—H16	119.9	N2—Zn1—Cl2	107.21 (5)
C16—C17—C18	120.1 (3)	N3—Zn1—Cl1	104.56 (5)
C16—C17—H17	119.9	N2—Zn1—Cl1	110.42 (5)
C18—C17—H17	119.9	Cl2—Zn1—Cl1	113.88 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cl1ⁱ	0.93	2.81	3.660 (2)	153
C28—H28···Cl1ⁱⁱ	0.93	2.80	3.502 (2)	133

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cl1ⁱ	0.93	2.81	3.660 (2)	153
C28—H28···Cl1ⁱⁱ	0.93	2.80	3.502 (2)	133

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z.

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Abdel-Ghani, N. T. & Mansour, A. M. (2011). J. Mol. Struct. 991, 108–126. CAS Google Scholar
Abdel-Ghani, N. T. & Mansour, A. M. (2012). Eur. J. Med. Chem. 47, 399–411. CAS PubMed Google Scholar
Ahuja, I. S. & Prasad, I. (1976). Inorg. Nucl. Chem. Lett. 12, 777–784. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Goudgaon, N. M., Dhondiba, V. & Vijayalaxmi, A. (2004). Indian J. Heterocycl. Chem. 13, 271–272. CAS Google Scholar
Mann, J., Baron, A., Opoku-Boahen, Y., Johansson, E., Parkinson, G., Kelland, L. R. & Neidle, S. (2001). J. Med. Chem. 44, 138–144. Web of Science CrossRef PubMed CAS Google Scholar
Naithani, P. K., Srivastava, V. K., Saxena, A. K., Barthwal, J. P., Gupta, T. K. & Shanker, K. (1990). Indian J. Exp. Biol. 28, 1145–1148. CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar