Di-μ-chlorido-bis­{chlorido[2,3-dimethyl-N-(pyridin-2-yl­methyl­idene)aniline-κ2N,N′]mercury(II)}

Hoseyni, S.J.; Talei Bavil Olyai, M.R.; Notash, B.

doi:10.1107/S1600536812039050

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page m1294

https://doi.org/10.1107/S1600536812039050

Open

access

Di-μ-chlorido-bis{chlorido[2,3-dimethyl-N-(pyridin-2-ylmethylidene)aniline-κ²N,N′]mercury(II)}

Seyed Jalal Hoseyni,^a Mohamad Reza Talei Bavil Olyai ^b ^* and Behrouz Notash ^c

^aDepartment of Chemistry, Islamic Azad University, Karaj Branch, Karaj, Iran, ^bDepartment of Chemistry, Faculty of Science, Islamic Azad University, South Tehran Branch, Tehran, Iran, and ^cDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: mr_talei@azad.ac.ir

(Received 31 August 2012; accepted 12 September 2012; online 22 September 2012)

In the centrosymmetric binuclear molecule of the title complex, [Hg₂Cl₄(C₁₄H₁₄N₂)₂], the five-coordinated Hg^II ions have a distorted square-pyramidal geometry defined by two N atoms belonging to the chelating iminopyridine ligand and three Cl atoms. The benzene and pyridine rings are oriented at a dihedral angle of 56.7 (6)°. The crystal packing is stabilized by C—H⋯Cl hydrogen bonds and π–π interactions between the pyridine rings [centroid–centroid distance = 3.796 (6) Å].

Related literature

For background to Schiff base compounds, see: Gibson et al. (2007 ); Gibson & Spitzmesser (2003 ); Ittel et al. (2000 ). For related structures, see: Baul et al. (2004 ).

Experimental

Crystal data

[Hg₂Cl₄(C₁₄H₁₄N₂)₂]
M_r = 963.52
Monoclinic, C 2/c
a = 7.7989 (16) Å
b = 26.525 (5) Å
c = 15.098 (3) Å
β = 98.26 (3)°
V = 3090.9 (11) Å³
Z = 4
Mo Kα radiation
μ = 10.29 mm⁻¹
T = 298 K
0.50 × 0.17 × 0.15 mm

Data collection

Stoe IPDS-2T diffractometer
Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2002 ) T_min = 0.126, T_max = 0.210
12121 measured reflections
4164 independent reflections
3174 reflections with I > 2σ(I)
R_int = 0.118

Refinement

R[F² > 2σ(F²)] = 0.083
wR(F²) = 0.206
S = 1.11
4164 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 3.28 e Å⁻³
Δρ_min = −4.88 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl2ⁱ	0.93	2.65	3.400 (11)	138
C4—H4⋯Cl2ⁱⁱ	0.93	2.67	3.552 (11)	158
C14—H14C⋯Cl1ⁱⁱⁱ	0.96	2.76	3.685 (14)	162
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (ii) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y+1, -z+2.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812039050/hy2585sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039050/hy2585Isup2.hkl

checkCIF report

Comment top

Schiff base metal complexes have been known since the nineteenth century. Investigation on metal-organic complexes represents one of the most active areas of material science and chemical research (Gibson et al., 2007; Gibson & Spitzmesser, 2003; Ittel et al., 2000). Schiff bases form a class of compounds with azomethin group, which are usually synthesized from the condensation of primary amines and active carbonyl groups by the elimination of water molecule. We report herein the crystal structure of the title compound, a new mercury(II) complex. This complex was synthesized by the reaction of HgCl₂ with 2-[(2,3-dimethylphenyl)iminomethyl]pyridine in an acetonitril solution.

In the title compound (Fig. 1), the Hg^II atom is five-coordinated in a distorted squar-pyramidal geometry. The Schiff base ligand coordinates to the Hg^II atom as a bidentate ligand through the N atoms of the imine group and pyridine ring. Also two bridging and one terminal chloride anions are present in the coordination environment of the Hg^II atom (Baul et al., 2004). The benzene and pyridine rings are oriented at a dihedral angle of 56.7 (6)°. Crystal packing is stabilized by intermolecular C—H···Cl hydrogen bonds (Fig. 2, Table 1) and π–π interactions between the pyridine rings [centroid–centroid distance = 3.796 (6) Å].

Related literature top

For background to Schiff base compounds, see: Gibson et al. (2007); Gibson & Spitzmesser (2003); Ittel et al. (2000). For related structures, see: Baul et al. (2004).

Experimental top

For the preparation of the title compound, a solution of 2-[(2,3-dimethylphenyl)iminomethyl]pyridine (0.210 g, 1.00 mmol) in acetonitril (10 ml) was added slowly to a solution of HgCl₂ (0.271 g, 1.00 mmol) in acetonitril (10 ml) and the resulting yellow solution was stirred for 45 min at room temperature. Then the yellow precipitate was filtered and dissolved in acetonitril and left to evaporate slowly at -18°C. After a few days, yellow crystals of the title compound were isolated (yield: 0.272 g, 56.5%; m.p. 489 K).

Structure description top

For background to Schiff base compounds, see: Gibson et al. (2007); Gibson & Spitzmesser (2003); Ittel et al. (2000). For related structures, see: Baul et al. (2004).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (a) 1/2-x, 3/2-y, 2-z.]
	Fig. 2. Packing diagram of the title compound. Hydrogen bonds are shown as blue dashed lines.

Di-µ-chlorido-bis{chlorido[2,3-dimethyl-N-(pyridin-2- ylmethylidene)aniline-κ²N,N']mercury(II)} top

Crystal data top

[Hg₂Cl₄(C₁₄H₁₄N₂)₂]	F(000) = 1808.0
M_r = 963.52	D_x = 2.071 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4164 reflections
a = 7.7989 (16) Å	θ = 2.1–29.2°
b = 26.525 (5) Å	µ = 10.29 mm⁻¹
c = 15.098 (3) Å	T = 298 K
β = 98.26 (3)°	Column, yellow
V = 3090.9 (11) Å³	0.50 × 0.17 × 0.15 mm
Z = 4

Data collection top

Stoe IPDS-2T diffractometer	4164 independent reflections
Radiation source: fine-focus sealed tube	3174 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.118
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 29.2°, θ_min = 2.1°
ω scans	h = −10→10
Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2002)	k = −36→35
T_min = 0.126, T_max = 0.210	l = −20→16
12121 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.083	H-atom parameters constrained
wR(F²) = 0.206	w = 1/[σ²(F_o²) + (0.1219P)²] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
4164 reflections	Δρ_max = 3.28 e Å⁻³
175 parameters	Δρ_min = −4.88 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0012 (2)

Crystal data top

[Hg₂Cl₄(C₁₄H₁₄N₂)₂]	V = 3090.9 (11) Å³
M_r = 963.52	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 7.7989 (16) Å	µ = 10.29 mm⁻¹
b = 26.525 (5) Å	T = 298 K
c = 15.098 (3) Å	0.50 × 0.17 × 0.15 mm
β = 98.26 (3)°

Data collection top

Stoe IPDS-2T diffractometer	4164 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2002)	3174 reflections with I > 2σ(I)
T_min = 0.126, T_max = 0.210	R_int = 0.118
12121 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.083	0 restraints
wR(F²) = 0.206	H-atom parameters constrained
S = 1.11	Δρ_max = 3.28 e Å⁻³
4164 reflections	Δρ_min = −4.88 e Å⁻³
175 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
Hg1	0.43296 (5)	0.703848 (14)	0.98975 (3)	0.0525 (2)
Cl2	0.1308 (3)	0.71572 (10)	0.88978 (17)	0.0524 (5)
Cl1	0.3754 (4)	0.64201 (11)	1.0936 (2)	0.0663 (7)
N1	0.5738 (9)	0.7612 (3)	0.9145 (5)	0.0452 (16)
N2	0.6082 (10)	0.6579 (3)	0.8873 (6)	0.0528 (19)
C5	0.6666 (12)	0.7441 (4)	0.8523 (6)	0.050 (2)
C6	0.6903 (13)	0.6896 (4)	0.8436 (7)	0.052 (2)
H6	0.7656	0.6776	0.8060	0.062*
C8	0.5112 (14)	0.5709 (4)	0.8740 (7)	0.057 (2)
C7	0.6450 (14)	0.6053 (4)	0.8836 (7)	0.058 (2)
C1	0.5528 (15)	0.8102 (4)	0.9243 (7)	0.055 (2)
H1	0.4887	0.8214	0.9678	0.066*
C13	0.3227 (15)	0.5888 (5)	0.8577 (9)	0.065 (3)
H13A	0.2696	0.5828	0.9102	0.098*
H13B	0.2608	0.5706	0.8081	0.098*
H13C	0.3194	0.6242	0.8445	0.098*
C12	0.8192 (15)	0.5889 (5)	0.8986 (8)	0.065 (3)
H12	0.9093	0.6122	0.9065	0.078*
C9	0.5443 (17)	0.5190 (5)	0.8768 (9)	0.068 (3)
C2	0.6211 (14)	0.8450 (4)	0.8733 (8)	0.060 (2)
H2	0.6030	0.8792	0.8814	0.072*
C4	0.7403 (13)	0.7770 (5)	0.7992 (7)	0.056 (2)
H4	0.8051	0.7649	0.7566	0.068*
C3	0.7178 (14)	0.8285 (5)	0.8093 (8)	0.062 (3)
H3	0.7669	0.8515	0.7736	0.074*
C14	0.406 (2)	0.4806 (5)	0.8639 (13)	0.092 (5)
H14A	0.3288	0.4876	0.8098	0.138*
H14B	0.3418	0.4814	0.9138	0.138*
H14C	0.4561	0.4478	0.8599	0.138*
C11	0.8530 (17)	0.5385 (5)	0.9014 (10)	0.080 (4)
H11	0.9672	0.5273	0.9101	0.096*
C10	0.7187 (19)	0.5035 (6)	0.8912 (10)	0.082 (4)
H10	0.7446	0.4693	0.8940	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.0468 (3)	0.0595 (3)	0.0521 (3)	0.00288 (15)	0.00989 (16)	0.00296 (15)
Cl2	0.0445 (11)	0.0637 (13)	0.0479 (11)	0.0022 (10)	0.0026 (9)	0.0021 (10)
Cl1	0.0688 (17)	0.0655 (14)	0.0649 (16)	0.0064 (12)	0.0102 (13)	0.0160 (12)
N1	0.034 (3)	0.064 (4)	0.037 (3)	−0.003 (3)	0.006 (3)	−0.009 (3)
N2	0.041 (4)	0.063 (5)	0.055 (4)	0.007 (4)	0.008 (3)	−0.013 (4)
C5	0.039 (4)	0.067 (6)	0.043 (4)	0.002 (4)	−0.002 (4)	0.000 (4)
C6	0.039 (4)	0.075 (6)	0.041 (4)	0.002 (4)	0.002 (4)	−0.006 (4)
C8	0.055 (5)	0.062 (5)	0.051 (5)	0.009 (5)	−0.003 (4)	−0.004 (4)
C7	0.047 (5)	0.073 (6)	0.053 (5)	0.009 (5)	0.003 (4)	−0.009 (5)
C1	0.056 (6)	0.058 (5)	0.053 (5)	0.004 (4)	0.012 (5)	0.003 (4)
C13	0.054 (6)	0.070 (6)	0.068 (7)	0.001 (5)	−0.002 (5)	0.001 (5)
C12	0.052 (6)	0.079 (7)	0.063 (6)	0.020 (5)	0.006 (5)	−0.010 (5)
C9	0.066 (7)	0.071 (7)	0.065 (7)	0.001 (6)	0.002 (5)	0.001 (5)
C2	0.050 (5)	0.062 (6)	0.064 (6)	−0.004 (5)	−0.001 (5)	0.004 (5)
C4	0.041 (5)	0.084 (7)	0.043 (5)	−0.006 (5)	0.004 (4)	−0.002 (5)
C3	0.052 (6)	0.079 (7)	0.053 (5)	−0.013 (5)	0.003 (5)	0.009 (5)
C14	0.089 (10)	0.059 (7)	0.125 (14)	0.008 (6)	0.001 (9)	0.001 (8)
C11	0.057 (7)	0.083 (8)	0.096 (10)	0.019 (6)	−0.005 (7)	−0.004 (7)
C10	0.083 (9)	0.074 (8)	0.084 (9)	0.022 (7)	−0.003 (7)	−0.005 (7)

Geometric parameters (Å, º) top

Hg1—N1	2.273 (8)	C13—H13A	0.9600
Hg1—Cl1	2.356 (3)	C13—H13B	0.9600
Hg1—N2	2.521 (8)	C13—H13C	0.9600
Hg1—Cl2	2.628 (3)	C12—C11	1.363 (18)
Hg1—Cl2ⁱ	2.893 (3)	C12—H12	0.9300
N1—C1	1.322 (14)	C9—C10	1.407 (18)
N1—C5	1.345 (13)	C9—C14	1.479 (19)
N2—C6	1.295 (14)	C2—C3	1.379 (17)
N2—C7	1.426 (14)	C2—H2	0.9300
C5—C4	1.365 (16)	C4—C3	1.390 (18)
C5—C6	1.466 (15)	C4—H4	0.9300
C6—H6	0.9300	C3—H3	0.9300
C8—C7	1.379 (16)	C14—H14A	0.9600
C8—C9	1.400 (17)	C14—H14B	0.9600
C8—C13	1.531 (15)	C14—H14C	0.9600
C7—C12	1.413 (14)	C11—C10	1.39 (2)
C1—C2	1.358 (16)	C11—H11	0.9300
C1—H1	0.9300	C10—H10	0.9300

N1—Hg1—Cl1	161.8 (2)	C8—C13—H13B	109.5
N1—Hg1—N2	70.9 (3)	H13A—C13—H13B	109.5
Cl1—Hg1—N2	104.1 (2)	C8—C13—H13C	109.5
N1—Hg1—Cl2	95.2 (2)	H13A—C13—H13C	109.5
Cl1—Hg1—Cl2	102.99 (10)	H13B—C13—H13C	109.5
N2—Hg1—Cl2	103.1 (2)	C11—C12—C7	119.0 (13)
N1—Hg1—Cl2ⁱ	87.7 (2)	C11—C12—H12	120.5
Cl1—Hg1—Cl2ⁱ	91.64 (10)	C7—C12—H12	120.5
N2—Hg1—Cl2ⁱ	154.2 (2)	C8—C9—C10	117.5 (12)
Cl2—Hg1—Cl2ⁱ	92.97 (7)	C8—C9—C14	123.0 (11)
Hg1—Cl2—Hg1ⁱ	87.03 (7)	C10—C9—C14	119.4 (13)
C1—N1—C5	119.7 (9)	C1—C2—C3	118.8 (11)
C1—N1—Hg1	121.8 (7)	C1—C2—H2	120.6
C5—N1—Hg1	118.2 (7)	C3—C2—H2	120.6
C6—N2—C7	119.9 (9)	C5—C4—C3	119.6 (10)
C6—N2—Hg1	110.4 (7)	C5—C4—H4	120.2
C7—N2—Hg1	128.9 (7)	C3—C4—H4	120.2
N1—C5—C4	120.7 (10)	C2—C3—C4	118.5 (10)
N1—C5—C6	118.7 (9)	C2—C3—H3	120.7
C4—C5—C6	120.6 (10)	C4—C3—H3	120.7
N2—C6—C5	121.2 (9)	C9—C14—H14A	109.5
N2—C6—H6	119.4	C9—C14—H14B	109.5
C5—C6—H6	119.4	H14A—C14—H14B	109.5
C7—C8—C9	121.0 (11)	C9—C14—H14C	109.5
C7—C8—C13	120.4 (10)	H14A—C14—H14C	109.5
C9—C8—C13	118.6 (11)	H14B—C14—H14C	109.5
C8—C7—C12	120.6 (11)	C12—C11—C10	120.8 (12)
C8—C7—N2	119.9 (9)	C12—C11—H11	119.6
C12—C7—N2	119.3 (10)	C10—C11—H11	119.6
N1—C1—C2	122.7 (11)	C11—C10—C9	121.2 (12)
N1—C1—H1	118.6	C11—C10—H10	119.4
C2—C1—H1	118.6	C9—C10—H10	119.4
C8—C13—H13A	109.5

N1—Hg1—Cl2—Hg1ⁱ	−88.0 (2)	C4—C5—C6—N2	−173.4 (9)
Cl1—Hg1—Cl2—Hg1ⁱ	92.38 (10)	C9—C8—C7—C12	−1.6 (18)
N2—Hg1—Cl2—Hg1ⁱ	−159.6 (2)	C13—C8—C7—C12	−180.0 (11)
Cl2ⁱ—Hg1—Cl2—Hg1ⁱ	0.0	C9—C8—C7—N2	−175.2 (11)
Cl1—Hg1—N1—C1	−105.9 (9)	C13—C8—C7—N2	6.4 (16)
N2—Hg1—N1—C1	177.2 (8)	C6—N2—C7—C8	−137.2 (11)
Cl2—Hg1—N1—C1	75.2 (7)	Hg1—N2—C7—C8	54.0 (13)
Cl2ⁱ—Hg1—N1—C1	−17.6 (7)	C6—N2—C7—C12	49.1 (15)
Cl1—Hg1—N1—C5	80.8 (9)	Hg1—N2—C7—C12	−119.7 (10)
N2—Hg1—N1—C5	3.9 (6)	C5—N1—C1—C2	0.3 (15)
Cl2—Hg1—N1—C5	−98.1 (6)	Hg1—N1—C1—C2	−172.9 (8)
Cl2ⁱ—Hg1—N1—C5	169.1 (6)	C8—C7—C12—C11	1.6 (19)
N1—Hg1—N2—C6	0.1 (6)	N2—C7—C12—C11	175.3 (12)
Cl1—Hg1—N2—C6	−161.6 (6)	C7—C8—C9—C10	1.1 (18)
Cl2—Hg1—N2—C6	91.2 (6)	C13—C8—C9—C10	179.5 (11)
Cl2ⁱ—Hg1—N2—C6	−35.8 (10)	C7—C8—C9—C14	−177.9 (13)
N1—Hg1—N2—C7	169.7 (9)	C13—C8—C9—C14	0.5 (19)
Cl1—Hg1—N2—C7	8.0 (8)	N1—C1—C2—C3	−0.7 (17)
Cl2—Hg1—N2—C7	−99.2 (8)	N1—C5—C4—C3	−0.5 (14)
Cl2ⁱ—Hg1—N2—C7	133.8 (7)	C6—C5—C4—C3	−179.3 (8)
C1—N1—C5—C4	0.3 (14)	C1—C2—C3—C4	0.5 (16)
Hg1—N1—C5—C4	173.8 (7)	C5—C4—C3—C2	0.1 (15)
C1—N1—C5—C6	179.1 (8)	C7—C12—C11—C10	−1 (2)
Hg1—N1—C5—C6	−7.5 (11)	C12—C11—C10—C9	1 (2)
C7—N2—C6—C5	−174.6 (8)	C8—C9—C10—C11	−1 (2)
Hg1—N2—C6—C5	−3.9 (11)	C14—C9—C10—C11	178.3 (15)
N1—C5—C6—N2	7.8 (13)

Symmetry code: (i) −x+1/2, −y+3/2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl2ⁱ	0.93	2.65	3.400 (11)	138
C4—H4···Cl2ⁱⁱ	0.93	2.67	3.552 (11)	158
C14—H14C···Cl1ⁱⁱⁱ	0.96	2.76	3.685 (14)	162

Symmetry codes: (i) −x+1/2, −y+3/2, −z+2; (ii) −x+1, y, −z+3/2; (iii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Hg₂Cl₄(C₁₄H₁₄N₂)₂]
M_r	963.52
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	7.7989 (16), 26.525 (5), 15.098 (3)
β (°)	98.26 (3)
V (Å³)	3090.9 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	10.29
Crystal size (mm)	0.50 × 0.17 × 0.15

Data collection
Diffractometer	Stoe IPDS2T
Absorption correction	Numerical (X-SHAPE and X-RED; Stoe & Cie, 2002)
T_min, T_max	0.126, 0.210
No. of measured, independent and observed [I > 2σ(I)] reflections	12121, 4164, 3174
R_int	0.118
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.206, 1.11
No. of reflections	4164
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	3.28, −4.88

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl2ⁱ	0.93	2.65	3.400 (11)	138
C4—H4···Cl2ⁱⁱ	0.93	2.67	3.552 (11)	158
C14—H14C···Cl1ⁱⁱⁱ	0.96	2.76	3.685 (14)	162

Symmetry codes: (i) −x+1/2, −y+3/2, −z+2; (ii) −x+1, y, −z+3/2; (iii) −x+1, −y+1, −z+2.

Acknowledgements

The authors acknowledge the Islamic Azad University, Karaj Branch, for financial support.

References

Baul, T. S. B., Lycka, A., Butcher, R. & Smith, E. F. (2004). Polyhedron, 23, 2323–2329. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gibson, V. C., Redshaw, C. & Solan, G. A. (2007). Chem. Rev. 107, 1745–1776. Web of Science CrossRef PubMed CAS Google Scholar
Gibson, V. C. & Spitzmesser, S. K. (2003). Chem. Rev. 103, 283–316. Web of Science CrossRef PubMed CAS Google Scholar
Ittel, S. D., Johnson, L. K. & Brookhart, M. (2000). Chem. Rev. 100, 1169–1203. Web of Science CrossRef PubMed CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.