Dichlorido[2-(3,5-dimethyl-1H-pyrazol-1-yl-κN2)quinoline-κN]zinc

Najib, M.H. bin; Tan, A.L.; Young, D.J.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812014390

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m571-m572

doi:10.1107/S1600536812014390

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Dichlorido[2-(3,5-dimethyl-1H-pyrazol-1-yl-κN²)quinoline-κN]zinc

Muhd. Hidayat bin Najib,^a Ai Ling Tan,^a David J. Young,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aFaculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link BE 1410, Negara Brunei Darussalam, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 3 April 2012; accepted 3 April 2012; online 13 April 2012)

The Zn^II atom in the title compound, [ZnCl₂(C₁₄H₁₃N₃)], is coordinated by a Cl₂N₂ donor set defined by quinoline and pyrazole N atoms of the chelating ligand and two Cl atoms. Distortions from the ideal tetrahedral geometry relate to the restricted bite angle of the chelating ligand [N—Zn—N = 78.54 (12)°]. In the crystal, molecules are connected into a three-dimensional structure by C—H⋯Cl interactions, involving both Cl atoms, and π–π interactions that occur between the pyrazole ring and each of the pyridine and benzene rings of the quinoline residue [intercentroid distances = 3.655 (2) and 3.676 (2) Å].

Related literature

For background to luminescent coordination complexes, see: Bai et al. (2012 ); Chou et al., (2011 ); Hu et al. (2011 ); Wang (2001 ). For the synthesis, see: Savel'eva et al. (2009 ); Scott et al. (1952 ).

Experimental

Crystal data

[ZnCl₂(C₁₄H₁₃N₃)]
M_r = 359.54
Monoclinic, P 2₁ /c
a = 14.3353 (10) Å
b = 8.7683 (5) Å
c = 11.9839 (8) Å
β = 102.181 (7)°
V = 1472.42 (17) Å³
Z = 4
Mo Kα radiation
μ = 2.02 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.597, T_max = 1.000
6070 measured reflections
3370 independent reflections
2438 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.124
S = 1.02
3370 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 1.04 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn—N1	2.021 (3)
Zn—N3	2.072 (3)
Zn—Cl1	2.2099 (11)
Zn—Cl2	2.2076 (11)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cl1ⁱ	0.98	2.81	3.680 (4)	148
C12—H12A⋯Cl2ⁱⁱ	0.95	2.82	3.579 (4)	138
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812014390/hg5206sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014390/hg5206Isup2.hkl

checkCIF report

Comment top

Luminescent coordination complexes are used as emitting materials in light-emitting devices (Chou et al., 2011) and it is known that many Zn^II nitrogen donor complexes are brightly luminescent in the blue region of the spectrum (Wang, 2001). The title compound (I) was prepared as part of our on-going quest for luminescent organometallic and coordination complexes with improved quantum efficiencies and colour purity (Bai et al., 2012; Hu et al., 2011;).

The Zn^II atom in (I), Fig. 1, is chelated by quinolinyl- and pyrazolyl-N atoms and two chloride atoms, Table 1. The resulting Cl₂N₂ donor set defines a tetrahedron with a significant distortion apparent owing to the restricted bite angle of the chelating ligand, i.e. N1—Zn—N3 78.54 (12)°; the remaining angles lie in the range 111.52 (9)°, for N1—Zn—Cl1, to 115.73 (9)°, for N1—Zn—Cl2. The five-membered chelate ring is essentially planar with a r.m.s. deviation = 0.035 Å with maximum deviations of 0.034 (3) and -0.029 (3) Å for the N2 and N1 atoms, respectively. A small twist is apparent in the bidentate ligand with the dihedral angle between the quinolinyl and pyrazolyl rings being 6.84 (17)°. The overall coordination geometry found for (I) matches that seen in the species carrying an additional methyl group in the 4-position of the quinolinyl residue (Savel'eva et al., 2009).

In the crystal packing, Fig. 2, molecules are connected into a three-dimensional architecture by C—H···Cl interactions, Table 1, involving both chloride atoms, and π—π interactions between the pyrazoyl ring and each of the pyridyl and benzene rings of the quinolinyl residue [inter-centroid distances = 3.655 (2) and 3.676 (2) Å, respectively; angles of inclination = 3.2 (2) and 3.5 (2)°, respectively; for symmetry operation: x, 1/2 - y, -1/2 + z].

Related literature top

For background to luminescent coordination complexes, see: Bai et al. (2012); Chou et al., (2011); Hu et al. (2011); Wang (2001). For the synthesis, see: Savel'eva et al. (2009); Scott et al. (1952).

Experimental top

The title compound was prepared by modification of literature procedures (Savel'eva et al., 2009; Scott et al. 1952). 3,5-Dimethyl-1-(2'-quinolyl)pyrazole (0.080 g) in a mixture of EtOH (4 ml) and CH₂Cl₂ (2 ml) was added to a solution of ZnCl₂ (0.061 g) in EtOH (8 ml). A white precipitate formed and was collected by filtration after 1 h, washed with EtOH and air-dried. The crude product was recrystallized from its CH₂Cl₂/hexane solution. Yield 0.054 g (42%). M. pt: 607–608 K. IR ν/cm^-1: 1619, 1596, 1579, 1559, 1511, 1479, 1439, 1386, 1380, 1346, 1319, 1142, 1090, 994, 983, 825, 783, 760.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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 DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the unit-cell contents of (I) in projection down the b axis. The C—H···Cl and π—π interactions are shown as orange and purple dashed lines, respectively.

Dichlorido[2-(3,5-dimethyl-1H-pyrazol-1-yl-κN²)quinoline- κN]zinc top

Crystal data top

[ZnCl₂(C₁₄H₁₃N₃)]	F(000) = 728
M_r = 359.54	D_x = 1.622 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1666 reflections
a = 14.3353 (10) Å	θ = 2.5–27.5°
b = 8.7683 (5) Å	µ = 2.02 mm⁻¹
c = 11.9839 (8) Å	T = 100 K
β = 102.181 (7)°	Plate, colourless
V = 1472.42 (17) Å³	0.25 × 0.20 × 0.02 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3370 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2438 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.047
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.7°
ω scan	h = −17→18
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→8
T_min = 0.597, T_max = 1.000	l = −9→15
6070 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0519P)² + 0.2907P] where P = (F_o² + 2F_c²)/3
3370 reflections	(Δ/σ)_max = 0.001
183 parameters	Δρ_max = 1.04 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

[ZnCl₂(C₁₄H₁₃N₃)]	V = 1472.42 (17) Å³
M_r = 359.54	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.3353 (10) Å	µ = 2.02 mm⁻¹
b = 8.7683 (5) Å	T = 100 K
c = 11.9839 (8) Å	0.25 × 0.20 × 0.02 mm
β = 102.181 (7)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3370 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2438 reflections with I > 2σ(I)
T_min = 0.597, T_max = 1.000	R_int = 0.047
6070 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.02	Δρ_max = 1.04 e Å⁻³
3370 reflections	Δρ_min = −0.66 e Å⁻³
183 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
Zn	0.26453 (3)	0.53715 (5)	0.58123 (4)	0.02140 (16)
Cl1	0.37804 (7)	0.65835 (11)	0.70222 (9)	0.0296 (3)
Cl2	0.14937 (7)	0.67975 (11)	0.48204 (9)	0.0300 (3)
N1	0.3193 (2)	0.3781 (3)	0.4912 (3)	0.0185 (7)
N3	0.2198 (2)	0.3372 (3)	0.6458 (3)	0.0179 (7)
C1	0.4079 (3)	0.5145 (4)	0.3689 (4)	0.0255 (9)
H1A	0.4758	0.5071	0.3671	0.038*
H1B	0.3979	0.6015	0.4163	0.038*
H1C	0.3706	0.5289	0.2911	0.038*
C2	0.3767 (3)	0.3710 (4)	0.4180 (3)	0.0194 (8)
C3	0.4000 (3)	0.2193 (4)	0.4009 (3)	0.0200 (8)
H3	0.4400	0.1841	0.3524	0.024*
C4	0.3546 (2)	0.1306 (4)	0.4674 (3)	0.0186 (8)
C5	0.3603 (3)	−0.0381 (4)	0.4822 (4)	0.0249 (9)
H5A	0.3798	−0.0626	0.5636	0.037*
H5B	0.4073	−0.0793	0.4415	0.037*
H5C	0.2977	−0.0833	0.4513	0.037*
C6	0.2458 (2)	0.2097 (4)	0.6031 (3)	0.0174 (8)
C7	0.2184 (3)	0.0628 (4)	0.6327 (3)	0.0189 (8)
H7A	0.2373	−0.0265	0.5984	0.023*
C8	0.1632 (3)	0.0549 (4)	0.7129 (3)	0.0207 (8)
H8A	0.1442	−0.0421	0.7358	0.025*
C9	0.1340 (2)	0.1877 (4)	0.7623 (3)	0.0186 (8)
C10	0.0765 (2)	0.1852 (4)	0.8457 (3)	0.0216 (8)
H10A	0.0563	0.0905	0.8710	0.026*
C11	0.0505 (3)	0.3181 (5)	0.8891 (3)	0.0243 (9)
H11A	0.0119	0.3161	0.9446	0.029*
C12	0.0805 (3)	0.4586 (4)	0.8521 (3)	0.0229 (9)
H12A	0.0617	0.5506	0.8830	0.027*
C13	0.1360 (3)	0.4656 (4)	0.7729 (3)	0.0222 (8)
H13A	0.1565	0.5614	0.7499	0.027*
C14	0.1628 (2)	0.3301 (4)	0.7257 (3)	0.0187 (8)
N2	0.3048 (2)	0.2299 (3)	0.5218 (3)	0.0173 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.0306 (3)	0.0144 (2)	0.0210 (3)	−0.00055 (19)	0.00946 (19)	0.00027 (19)
Cl1	0.0423 (6)	0.0242 (5)	0.0237 (6)	−0.0104 (4)	0.0104 (4)	−0.0047 (4)
Cl2	0.0364 (6)	0.0193 (5)	0.0355 (6)	0.0071 (4)	0.0102 (5)	0.0038 (4)
N1	0.0250 (16)	0.0152 (16)	0.0151 (16)	−0.0005 (13)	0.0042 (13)	−0.0004 (13)
N3	0.0248 (16)	0.0180 (16)	0.0116 (16)	−0.0026 (13)	0.0054 (13)	−0.0017 (13)
C1	0.031 (2)	0.024 (2)	0.021 (2)	−0.0040 (18)	0.0050 (17)	0.0009 (17)
C2	0.0212 (18)	0.023 (2)	0.0139 (19)	−0.0034 (16)	0.0029 (15)	0.0013 (16)
C3	0.0205 (18)	0.024 (2)	0.0145 (19)	0.0024 (16)	0.0024 (14)	0.0005 (16)
C4	0.0213 (18)	0.0184 (19)	0.0154 (19)	0.0020 (16)	0.0025 (15)	−0.0039 (16)
C5	0.033 (2)	0.017 (2)	0.028 (2)	0.0027 (17)	0.0137 (18)	0.0029 (17)
C6	0.0211 (19)	0.0185 (19)	0.0113 (19)	−0.0014 (16)	0.0004 (14)	−0.0012 (15)
C7	0.0243 (19)	0.0157 (18)	0.0168 (19)	−0.0003 (16)	0.0047 (15)	−0.0017 (15)
C8	0.027 (2)	0.0168 (19)	0.019 (2)	−0.0016 (16)	0.0064 (16)	0.0047 (16)
C9	0.0199 (18)	0.0198 (19)	0.0149 (19)	−0.0009 (16)	0.0011 (14)	0.0004 (16)
C10	0.024 (2)	0.023 (2)	0.018 (2)	−0.0061 (16)	0.0044 (16)	0.0004 (17)
C11	0.024 (2)	0.033 (2)	0.018 (2)	−0.0044 (18)	0.0078 (16)	−0.0030 (18)
C12	0.0244 (19)	0.025 (2)	0.019 (2)	0.0049 (17)	0.0024 (16)	−0.0033 (17)
C13	0.0230 (19)	0.023 (2)	0.020 (2)	−0.0048 (17)	0.0036 (16)	0.0005 (17)
C14	0.0191 (18)	0.0210 (19)	0.0153 (19)	0.0005 (16)	0.0020 (15)	0.0021 (16)
N2	0.0230 (16)	0.0139 (15)	0.0152 (16)	−0.0003 (13)	0.0039 (13)	0.0007 (13)

Geometric parameters (Å, º) top

Zn—N1	2.021 (3)	C5—H5B	0.9800
Zn—N3	2.072 (3)	C5—H5C	0.9800
Zn—Cl1	2.2099 (11)	C6—C7	1.414 (5)
Zn—Cl2	2.2076 (11)	C6—N2	1.429 (5)
N1—C2	1.325 (5)	C7—C8	1.370 (5)
N1—N2	1.378 (4)	C7—H7A	0.9500
N3—C6	1.316 (5)	C8—C9	1.409 (5)
N3—C14	1.385 (5)	C8—H8A	0.9500
C1—C2	1.497 (5)	C9—C14	1.414 (5)
C1—H1A	0.9800	C9—C10	1.423 (5)
C1—H1B	0.9800	C10—C11	1.361 (5)
C1—H1C	0.9800	C10—H10A	0.9500
C2—C3	1.397 (5)	C11—C12	1.407 (5)
C3—C4	1.373 (5)	C11—H11A	0.9500
C3—H3	0.9500	C12—C13	1.362 (5)
C4—N2	1.375 (4)	C12—H12A	0.9500
C4—C5	1.490 (5)	C13—C14	1.403 (5)
C5—H5A	0.9800	C13—H13A	0.9500

N1—Zn—N3	78.54 (12)	H5B—C5—H5C	109.5
N1—Zn—Cl2	115.73 (9)	N3—C6—C7	124.0 (3)
N3—Zn—Cl2	115.15 (9)	N3—C6—N2	114.6 (3)
N1—Zn—Cl1	111.52 (9)	C7—C6—N2	121.3 (3)
N3—Zn—Cl1	113.89 (9)	C8—C7—C6	117.0 (3)
Cl2—Zn—Cl1	116.38 (4)	C8—C7—H7A	121.5
C2—N1—N2	106.4 (3)	C6—C7—H7A	121.5
C2—N1—Zn	138.7 (3)	C7—C8—C9	121.3 (3)
N2—N1—Zn	114.3 (2)	C7—C8—H8A	119.3
C6—N3—C14	119.2 (3)	C9—C8—H8A	119.3
C6—N3—Zn	116.0 (2)	C8—C9—C14	117.9 (3)
C14—N3—Zn	124.8 (2)	C8—C9—C10	123.3 (3)
C2—C1—H1A	109.5	C14—C9—C10	118.8 (3)
C2—C1—H1B	109.5	C11—C10—C9	120.1 (4)
H1A—C1—H1B	109.5	C11—C10—H10A	119.9
C2—C1—H1C	109.5	C9—C10—H10A	119.9
H1A—C1—H1C	109.5	C10—C11—C12	120.2 (4)
H1B—C1—H1C	109.5	C10—C11—H11A	119.9
N1—C2—C3	110.0 (3)	C12—C11—H11A	119.9
N1—C2—C1	120.0 (3)	C13—C12—C11	121.4 (4)
C3—C2—C1	129.9 (3)	C13—C12—H12A	119.3
C4—C3—C2	107.3 (3)	C11—C12—H12A	119.3
C4—C3—H3	126.3	C12—C13—C14	119.5 (4)
C2—C3—H3	126.3	C12—C13—H13A	120.3
C3—C4—N2	105.9 (3)	C14—C13—H13A	120.3
C3—C4—C5	127.7 (3)	N3—C14—C13	119.5 (3)
N2—C4—C5	126.4 (3)	N3—C14—C9	120.5 (3)
C4—C5—H5A	109.5	C13—C14—C9	120.0 (3)
C4—C5—H5B	109.5	C4—N2—N1	110.4 (3)
H5A—C5—H5B	109.5	C4—N2—C6	133.3 (3)
C4—C5—H5C	109.5	N1—N2—C6	116.3 (3)
H5A—C5—H5C	109.5

N3—Zn—N1—C2	−172.9 (4)	C7—C8—C9—C10	179.8 (4)
Cl2—Zn—N1—C2	74.6 (4)	C8—C9—C10—C11	−179.6 (3)
Cl1—Zn—N1—C2	−61.5 (4)	C14—C9—C10—C11	−0.2 (5)
N3—Zn—N1—N2	−3.5 (2)	C9—C10—C11—C12	−0.2 (5)
Cl2—Zn—N1—N2	−116.1 (2)	C10—C11—C12—C13	−0.2 (6)
Cl1—Zn—N1—N2	107.8 (2)	C11—C12—C13—C14	1.0 (6)
N1—Zn—N3—C6	0.5 (2)	C6—N3—C14—C13	179.0 (3)
Cl2—Zn—N3—C6	113.7 (2)	Zn—N3—C14—C13	−3.6 (5)
Cl1—Zn—N3—C6	−108.2 (2)	C6—N3—C14—C9	0.9 (5)
N1—Zn—N3—C14	−177.0 (3)	Zn—N3—C14—C9	178.3 (2)
Cl2—Zn—N3—C14	−63.8 (3)	C12—C13—C14—N3	−179.5 (3)
Cl1—Zn—N3—C14	74.3 (3)	C12—C13—C14—C9	−1.5 (5)
N2—N1—C2—C3	−0.2 (4)	C8—C9—C14—N3	−1.5 (5)
Zn—N1—C2—C3	169.6 (3)	C10—C9—C14—N3	179.1 (3)
N2—N1—C2—C1	−179.2 (3)	C8—C9—C14—C13	−179.6 (3)
Zn—N1—C2—C1	−9.3 (6)	C10—C9—C14—C13	1.1 (5)
N1—C2—C3—C4	−0.1 (4)	C3—C4—N2—N1	−0.6 (4)
C1—C2—C3—C4	178.7 (4)	C5—C4—N2—N1	177.2 (3)
C2—C3—C4—N2	0.5 (4)	C3—C4—N2—C6	−178.4 (4)
C2—C3—C4—C5	−177.3 (4)	C5—C4—N2—C6	−0.6 (6)
C14—N3—C6—C7	0.7 (5)	C2—N1—N2—C4	0.5 (4)
Zn—N3—C6—C7	−176.9 (3)	Zn—N1—N2—C4	−172.2 (2)
C14—N3—C6—N2	−179.8 (3)	C2—N1—N2—C6	178.7 (3)
Zn—N3—C6—N2	2.6 (4)	Zn—N1—N2—C6	6.0 (4)
N3—C6—C7—C8	−1.7 (5)	N3—C6—N2—C4	172.0 (3)
N2—C6—C7—C8	178.9 (3)	C7—C6—N2—C4	−8.5 (6)
C6—C7—C8—C9	1.0 (6)	N3—C6—N2—N1	−5.7 (4)
C7—C8—C9—C14	0.5 (5)	C7—C6—N2—N1	173.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cl1ⁱ	0.98	2.81	3.680 (4)	148
C12—H12A···Cl2ⁱⁱ	0.95	2.82	3.579 (4)	138

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

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₄H₁₃N₃)]
M_r	359.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.3353 (10), 8.7683 (5), 11.9839 (8)
β (°)	102.181 (7)
V (Å³)	1472.42 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.02
Crystal size (mm)	0.25 × 0.20 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.597, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6070, 3370, 2438
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.124, 1.02
No. of reflections	3370
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.04, −0.66

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Zn—N1	2.021 (3)	Zn—Cl1	2.2099 (11)
Zn—N3	2.072 (3)	Zn—Cl2	2.2076 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cl1ⁱ	0.98	2.81	3.680 (4)	148
C12—H12A···Cl2ⁱⁱ	0.95	2.82	3.579 (4)	138

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

Footnotes

‡Additional correspondence author, e-mail: david.young@ubd.edu.bn.

Acknowledgements

We gratefully acknowledge funding from the Brunei Research Council, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/3).

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Bai, S.-Q., Young, A. M., Hu, J. J., Young, D. J., Zhang, X., Zong, Y., Xu, J., Zuo, J.-L. & Hor, T. S. A. (2012). CrystEngComm, 14, 961–971. Web of Science CSD CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Chou, P.-T., Chi, Y., Chung, M.-W. & Lin, C.-C. (2011). Coord. Chem. Rev. 255, 2653–2665. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hu, J. J., Bai, S. Q., Yeh, H. H., Young, D. J., Chi, Y. & Hor, T. S. A. (2011). Dalton Trans. 40, 4402–4406. Web of Science CSD CrossRef CAS PubMed Google Scholar
Savel'eva, Z. A., Popov, S. A., Klevtsova, R. F., Glinskaya, L. A., Uskov, E. M., Tkachev, A. V. & Larionov, S. V. (2009). Russ. Chem. Bull. Int. Ed. 58, 1837–1840. CAS Google Scholar
Scott, F. L., Crowley, K. M. & Reilly, J. (1952). J. Am. Chem. Soc. 74, 3444–3445. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, S. (2001). Coord. Chem. Rev. 215, 79–98. Web of Science CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar