Dichlorido(2,9-dimeth­oxy-1,10-phenanthroline-κ2N,N′)zinc(II)

Niu, C.-Y.; Su, H.; Meng, L.; Kou, C.-H.

doi:10.1107/S160053680902491X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m869

doi:10.1107/S160053680902491X

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Dichlorido(2,9-dimethoxy-1,10-phenanthroline-κ²N,N′)zinc(II)

Cao-Yuan Niu,^a ^* Hui Su,^a Lei Meng ^a and Chun-Hong Kou ^a

^aCollege of Sciences, Henan Agricultural University, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: niu_cy2000@yahoo.com.cn

(Received 13 June 2009; accepted 28 June 2009; online 4 July 2009)

In the crystal structure of the title compound, [ZnCl₂(C₁₄H₁₂N₂O₂)], the Zn^II center is four-coordinated by two N atoms from one 2,9-dimethoxy-1,10-phenanthroline ligand and two Cl atoms. The coordination geometry is distorted tetrahedral, as the Zn—N bond distances are shorter than the Zn—Cl distances, and the Cl—Zn—N and Cl—Zn—Cl bond angles are much larger than the N—Zn—N angle. For the ligand, the O and C atoms of the methoxy groups are almost in the plane defined by the phenanthroline ring. The two O atoms deviate from the phenanthroline mean plane by 0.076 (2) and 0.084 (2) Å, and the two methyl C atoms deviate from the phenanthroline mean plane by 0.035 (3) and 0.361 (3) Å. There are medium π–π stacking interactions between two parallel phenanthroline rings with a centroid–centroid distance of 3.7860 (2) Å and a dihedral angle between the plane defined by the two parallel phenanthroline rings of 1.13 (5)°.

Related literature

For background information, see: Majumder et al. (2006 ); Bie et al. (2006 ). For the synthesis, see: Pijper et al. (1984 ).

Experimental

Crystal data

[ZnCl₂(C₁₄H₁₂N₂O₂)]
M_r = 376.53
Monoclinic, P 2₁ /c
a = 9.0494 (8) Å
b = 10.3783 (9) Å
c = 16.3517 (14) Å
β = 99.022 (1)°
V = 1516.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.98 mm⁻¹
T = 291 K
0.27 × 0.14 × 0.10 mm

Data collection

Bruker APEXII CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.616, T_max = 0.835
9326 measured reflections
3465 independent reflections
2917 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.065
S = 1.03
3465 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—N1	2.0659 (14)
Zn1—N2	2.0911 (14)
Zn1—Cl1	2.2007 (6)
Zn1—Cl2	2.2219 (6)

N1—Zn1—N2	80.58 (6)
N1—Zn1—Cl1	113.27 (4)
N2—Zn1—Cl1	120.54 (4)
N1—Zn1—Cl2	110.66 (4)
N2—Zn1—Cl2	108.06 (4)
Cl1—Zn1—Cl2	117.82 (2)

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1994 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 and DIAMOND (Brandenburg, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, globsl. DOI: 10.1107/S160053680902491X/fj2228sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902491X/fj2228Isup2.hkl

checkCIF report

Comment top

The compound 1,10-phenanthroline was reported to be used to synthesize some potential strong luminescent materials with d¹⁰ metals. It can be predicted that the title compound that composed of a derivative of 1,10-phenanthroline and a d¹⁰metal zinc would possess strong ligand to ligand or metal perturbed ligand to ligand emissions (Majumder et al., 2006; Bie, et al., 2006). 2,9-Dimethoxy-1,10-phenanthroline and 2,9-Diethoxy-1,10-phenanthroline as derivatives of 1,10-phenanthroline were synthesized at early time and they possess antimycoplasmal activity in the presence of copper (Pijper, et al., 1984).

The title compound (I) is a mononuclear zinc(II) complex of 2,9-dimethoxy-1,10-phenanthroline (shown as Fig.1). The zinc metal centre is four coordinated to two nitrogen atoms (N1, N2) from the 1,10-phenanthroline ring and two independent chlorine atoms (Cl1, Cl2), defining a deformed tetrahedron coordination geometry around the metal center. The Zn—Cl bond distances are 2.2007 (6) and 2.2219 (6) Å, which are longer than the Zn—N bond distances from 2.0659 (14) to 2.0911 (14) Å. The Cl—Zn—N and Cl—Zn—Cl bond angles are at the range of 108.06 (4) to 120.54 (4) °, which are larger than that of N—Zn—N [80.58 (6)°]. Furthermore, there are medium π-π stackings between two parallel phenanthroline rings from two symmetry-related monomers with the centroid-to-centroid distances of about 3.7860 (2) Å and dihedral angle of 1.13 (5) ° (Fig. 2). For the ligand, two methoxy groups are basically coplanar to the phenanthroline ring. Two oxygen atoms deviate from the phenanthroline plane by 0.076 (2) and 0.084 (2) Å, and two methyl carbon atoms deviate from the phenanthroline plane by 0.035 (3) and 0.361 (3) Å.

Three-dimensional supramolecular structure of the title compound is formed via the above-mentioned π-π stackings and weak van der waals interactions. Some interesting packings along three crystallographic directions can be seen from Fig. 3.

Related literature top

For background information, see: Majumder et al. (2006); Bie et al. (2006). For the synthesis, see: Pijper et al. (1984).

Experimental top

The organic ligand 2,9-dimethoxy-1,10-phenanthroline was prepared according to the procedure of literature (Pijper, et al., 1984). The slow evaporation of mixture of the ligand (0.022 g, 0.1 mmol) and zinc dichloride (0.014 g, 0.1 mmol) in 30 ml me thanol afforded suitable colourless block crystals in about 7 days (yield 45%).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: 'SHELXL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the Zn^II coordination environment in (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Packing diagram showing the π-π interaction (purple dotted line). All H atoms have been omitted for clarity.
	Fig. 3. Diagrams showing the three-dimensional packing forms along three crystallographic directions.

Dichlorido(2,9-dimethoxy-1,10-phenanthroline-κ²N,N')zinc(II) top

Crystal data top

[ZnCl₂(C₁₄H₁₂N₂O₂)]	F(000) = 760
M_r = 376.53	D_x = 1.649 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4023 reflections
a = 9.0494 (8) Å	θ = 2.3–27.9°
b = 10.3783 (9) Å	µ = 1.98 mm⁻¹
c = 16.3517 (14) Å	T = 291 K
β = 99.022 (1)°	Block, colorless
V = 1516.7 (2) Å³	0.27 × 0.14 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD detector diffractometer	3465 independent reflections
Radiation source: fine-focus sealed tube	2917 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→11
T_min = 0.616, T_max = 0.835	k = −13→13
9326 measured reflections	l = −21→21

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0298P)² + 0.4767P] where P = (F_o² + 2F_c²)/3
3465 reflections	(Δ/σ)_max = 0.001
192 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[ZnCl₂(C₁₄H₁₂N₂O₂)]	V = 1516.7 (2) Å³
M_r = 376.53	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0494 (8) Å	µ = 1.98 mm⁻¹
b = 10.3783 (9) Å	T = 291 K
c = 16.3517 (14) Å	0.27 × 0.14 × 0.10 mm
β = 99.022 (1)°

Data collection top

Bruker APEXII CCD detector diffractometer	3465 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2917 reflections with I > 2σ(I)
T_min = 0.616, T_max = 0.835	R_int = 0.017
9326 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
3465 reflections	Δρ_min = −0.25 e Å⁻³
192 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
Zn1	0.85210 (2)	0.73107 (2)	0.142693 (13)	0.03691 (8)
Cl1	1.07679 (6)	0.76186 (5)	0.21365 (3)	0.05122 (14)
Cl2	0.68839 (6)	0.89157 (5)	0.13748 (4)	0.05898 (15)
O1	0.99184 (17)	0.81556 (14)	−0.01403 (8)	0.0502 (3)
O2	0.71476 (16)	0.58258 (13)	0.28668 (8)	0.0481 (3)
N1	0.85558 (16)	0.65629 (14)	0.02592 (9)	0.0366 (3)
N2	0.73776 (16)	0.55838 (14)	0.15361 (9)	0.0360 (3)
C1	0.9193 (2)	0.70500 (19)	−0.03500 (11)	0.0405 (4)
C2	0.9063 (3)	0.6460 (2)	−0.11341 (12)	0.0502 (5)
H2	0.9523	0.6820	−0.1550	0.060*
C3	0.8256 (3)	0.5361 (2)	−0.12718 (12)	0.0519 (5)
H3	0.8160	0.4967	−0.1788	0.062*
C4	0.7557 (2)	0.48020 (19)	−0.06404 (12)	0.0447 (4)
C5	0.6660 (2)	0.3663 (2)	−0.07373 (14)	0.0548 (5)
H5	0.6523	0.3232	−0.1242	0.066*
C6	0.6011 (2)	0.3201 (2)	−0.01103 (14)	0.0540 (5)
H6	0.5415	0.2468	−0.0192	0.065*
C7	0.6228 (2)	0.38262 (18)	0.06829 (13)	0.0434 (4)
C8	0.5595 (2)	0.3401 (2)	0.13704 (14)	0.0500 (5)
H8	0.4985	0.2675	0.1319	0.060*
C9	0.5859 (2)	0.40325 (19)	0.21063 (13)	0.0464 (5)
H9	0.5437	0.3748	0.2557	0.056*
C10	0.6789 (2)	0.51305 (18)	0.21712 (12)	0.0391 (4)
C11	0.71040 (19)	0.49372 (17)	0.07990 (11)	0.0369 (4)
C12	0.7758 (2)	0.54491 (17)	0.01209 (11)	0.0367 (4)
C13	1.0711 (3)	0.8779 (2)	−0.07353 (13)	0.0554 (5)
H13A	1.1445	0.8199	−0.0891	0.083*
H13B	1.1199	0.9540	−0.0492	0.083*
H13C	1.0014	0.9013	−0.1217	0.083*
C14	0.6826 (3)	0.5280 (2)	0.36304 (12)	0.0536 (5)
H14A	0.5763	0.5196	0.3604	0.080*
H14B	0.7216	0.5834	0.4083	0.080*
H14C	0.7285	0.4447	0.3712	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03791 (13)	0.03966 (13)	0.03454 (12)	−0.00516 (9)	0.01002 (9)	−0.00396 (8)
Cl1	0.0399 (3)	0.0714 (4)	0.0431 (3)	−0.0099 (2)	0.0087 (2)	−0.0143 (2)
Cl2	0.0501 (3)	0.0513 (3)	0.0795 (4)	0.0074 (2)	0.0226 (3)	−0.0024 (3)
O1	0.0623 (9)	0.0531 (8)	0.0391 (7)	−0.0104 (7)	0.0201 (6)	0.0019 (6)
O2	0.0561 (9)	0.0513 (8)	0.0389 (7)	−0.0155 (7)	0.0138 (6)	0.0014 (6)
N1	0.0378 (8)	0.0402 (9)	0.0323 (7)	0.0027 (6)	0.0071 (6)	−0.0009 (6)
N2	0.0342 (8)	0.0367 (8)	0.0370 (8)	−0.0032 (6)	0.0057 (6)	0.0017 (6)
C1	0.0419 (10)	0.0461 (11)	0.0342 (9)	0.0081 (8)	0.0083 (8)	0.0043 (8)
C2	0.0608 (13)	0.0582 (13)	0.0339 (10)	0.0133 (10)	0.0148 (9)	0.0022 (9)
C3	0.0647 (14)	0.0557 (13)	0.0348 (10)	0.0144 (11)	0.0057 (9)	−0.0088 (9)
C4	0.0468 (11)	0.0458 (11)	0.0392 (10)	0.0126 (9)	−0.0006 (8)	−0.0068 (8)
C5	0.0601 (13)	0.0487 (12)	0.0520 (12)	0.0071 (10)	−0.0030 (10)	−0.0183 (10)
C6	0.0510 (12)	0.0410 (11)	0.0661 (14)	−0.0020 (9)	−0.0028 (10)	−0.0123 (10)
C7	0.0364 (10)	0.0381 (10)	0.0530 (11)	0.0008 (8)	−0.0007 (8)	−0.0035 (8)
C8	0.0405 (11)	0.0411 (11)	0.0660 (14)	−0.0081 (9)	0.0011 (10)	0.0013 (10)
C9	0.0405 (11)	0.0448 (11)	0.0544 (12)	−0.0067 (8)	0.0087 (9)	0.0086 (9)
C10	0.0353 (9)	0.0400 (10)	0.0422 (10)	−0.0016 (7)	0.0065 (8)	0.0039 (8)
C11	0.0322 (9)	0.0356 (9)	0.0411 (9)	0.0038 (7)	0.0006 (7)	−0.0018 (7)
C12	0.0345 (9)	0.0377 (10)	0.0365 (9)	0.0072 (7)	0.0009 (7)	−0.0021 (7)
C13	0.0574 (13)	0.0644 (14)	0.0490 (12)	−0.0040 (11)	0.0226 (10)	0.0113 (10)
C14	0.0590 (13)	0.0624 (14)	0.0427 (11)	−0.0119 (11)	0.0179 (10)	0.0042 (9)

Geometric parameters (Å, º) top

Zn1—N1	2.0659 (14)	C4—C5	1.429 (3)
Zn1—N2	2.0911 (14)	C5—C6	1.347 (3)
Zn1—Cl1	2.2007 (6)	C5—H5	0.9300
Zn1—Cl2	2.2219 (6)	C6—C7	1.436 (3)
O1—C1	1.340 (2)	C6—H6	0.9300
O1—C13	1.449 (2)	C7—C11	1.395 (3)
O2—C10	1.343 (2)	C7—C8	1.410 (3)
O2—C14	1.442 (2)	C8—C9	1.358 (3)
N1—C1	1.327 (2)	C8—H8	0.9300
N1—C12	1.363 (2)	C9—C10	1.411 (3)
N2—C10	1.325 (2)	C9—H9	0.9300
N2—C11	1.368 (2)	C11—C12	1.438 (3)
C1—C2	1.409 (3)	C13—H13A	0.9600
C2—C3	1.354 (3)	C13—H13B	0.9600
C2—H2	0.9300	C13—H13C	0.9600
C3—C4	1.417 (3)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—C12	1.401 (3)	C14—H14C	0.9600

N1—Zn1—N2	80.58 (6)	C7—C6—H6	119.6
N1—Zn1—Cl1	113.27 (4)	C11—C7—C8	116.32 (18)
N2—Zn1—Cl1	120.54 (4)	C11—C7—C6	119.39 (19)
N1—Zn1—Cl2	110.66 (4)	C8—C7—C6	124.29 (19)
N2—Zn1—Cl2	108.06 (4)	C9—C8—C7	121.19 (18)
Cl1—Zn1—Cl2	117.82 (2)	C9—C8—H8	119.4
C1—O1—C13	119.03 (15)	C7—C8—H8	119.4
C10—O2—C14	117.89 (15)	C8—C9—C10	118.47 (19)
C1—N1—C12	118.68 (16)	C8—C9—H9	120.8
C1—N1—Zn1	128.47 (13)	C10—C9—H9	120.8
C12—N1—Zn1	112.80 (11)	N2—C10—O2	113.56 (16)
C10—N2—C11	118.48 (16)	N2—C10—C9	122.41 (18)
C10—N2—Zn1	129.50 (13)	O2—C10—C9	124.03 (17)
C11—N2—Zn1	111.65 (11)	N2—C11—C7	123.09 (17)
N1—C1—O1	112.80 (16)	N2—C11—C12	117.31 (16)
N1—C1—C2	122.24 (19)	C7—C11—C12	119.60 (17)
O1—C1—C2	124.95 (17)	N1—C12—C4	123.06 (17)
C3—C2—C1	118.91 (19)	N1—C12—C11	117.18 (15)
C3—C2—H2	120.5	C4—C12—C11	119.76 (17)
C1—C2—H2	120.5	O1—C13—H13A	109.5
C2—C3—C4	120.96 (18)	O1—C13—H13B	109.5
C2—C3—H3	119.5	H13A—C13—H13B	109.5
C4—C3—H3	119.5	O1—C13—H13C	109.5
C12—C4—C3	116.14 (19)	H13A—C13—H13C	109.5
C12—C4—C5	119.19 (19)	H13B—C13—H13C	109.5
C3—C4—C5	124.66 (18)	O2—C14—H14A	109.5
C6—C5—C4	121.18 (19)	O2—C14—H14B	109.5
C6—C5—H5	119.4	H14A—C14—H14B	109.5
C4—C5—H5	119.4	O2—C14—H14C	109.5
C5—C6—C7	120.8 (2)	H14A—C14—H14C	109.5
C5—C6—H6	119.6	H14B—C14—H14C	109.5

N2—Zn1—N1—C1	−177.42 (16)	C7—C8—C9—C10	−0.1 (3)
Cl1—Zn1—N1—C1	−58.12 (16)	C11—N2—C10—O2	178.99 (16)
Cl2—Zn1—N1—C1	76.72 (16)	Zn1—N2—C10—O2	−8.7 (2)
N2—Zn1—N1—C12	5.17 (12)	C11—N2—C10—C9	−1.9 (3)
Cl1—Zn1—N1—C12	124.47 (11)	Zn1—N2—C10—C9	170.42 (14)
Cl2—Zn1—N1—C12	−100.69 (12)	C14—O2—C10—N2	−167.68 (17)
N1—Zn1—N2—C10	−179.01 (17)	C14—O2—C10—C9	13.3 (3)
Cl1—Zn1—N2—C10	69.45 (17)	C8—C9—C10—N2	1.8 (3)
Cl2—Zn1—N2—C10	−70.22 (16)	C8—C9—C10—O2	−179.18 (18)
N1—Zn1—N2—C11	−6.24 (12)	C10—N2—C11—C7	0.3 (3)
Cl1—Zn1—N2—C11	−117.78 (11)	Zn1—N2—C11—C7	−173.33 (14)
Cl2—Zn1—N2—C11	102.56 (11)	C10—N2—C11—C12	−179.91 (16)
C12—N1—C1—O1	178.81 (15)	Zn1—N2—C11—C12	6.43 (19)
Zn1—N1—C1—O1	1.5 (2)	C8—C7—C11—N2	1.3 (3)
C12—N1—C1—C2	0.5 (3)	C6—C7—C11—N2	−179.37 (17)
Zn1—N1—C1—C2	−176.81 (14)	C8—C7—C11—C12	−178.48 (17)
C13—O1—C1—N1	178.04 (17)	C6—C7—C11—C12	0.9 (3)
C13—O1—C1—C2	−3.7 (3)	C1—N1—C12—C4	−1.1 (3)
N1—C1—C2—C3	0.2 (3)	Zn1—N1—C12—C4	176.62 (14)
O1—C1—C2—C3	−177.93 (19)	C1—N1—C12—C11	178.97 (16)
C1—C2—C3—C4	−0.3 (3)	Zn1—N1—C12—C11	−3.35 (19)
C2—C3—C4—C12	−0.2 (3)	C3—C4—C12—N1	0.9 (3)
C2—C3—C4—C5	178.6 (2)	C5—C4—C12—N1	−177.93 (17)
C12—C4—C5—C6	−0.2 (3)	C3—C4—C12—C11	−179.10 (17)
C3—C4—C5—C6	−178.9 (2)	C5—C4—C12—C11	2.0 (3)
C4—C5—C6—C7	−1.4 (3)	N2—C11—C12—N1	−2.2 (2)
C5—C6—C7—C11	1.0 (3)	C7—C11—C12—N1	177.58 (16)
C5—C6—C7—C8	−179.7 (2)	N2—C11—C12—C4	177.84 (16)
C11—C7—C8—C9	−1.4 (3)	C7—C11—C12—C4	−2.4 (3)
C6—C7—C8—C9	179.3 (2)

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₄H₁₂N₂O₂)]
M_r	376.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	9.0494 (8), 10.3783 (9), 16.3517 (14)
β (°)	99.022 (1)
V (Å³)	1516.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.98
Crystal size (mm)	0.27 × 0.14 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.616, 0.835
No. of measured, independent and observed [I > 2σ(I)] reflections	9326, 3465, 2917
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.065, 1.03
No. of reflections	3465
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.25

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1994), SHELXS97 (Sheldrick, 2008), 'SHELXL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005).

Selected geometric parameters (Å, º) top

Zn1—N1	2.0659 (14)	Zn1—Cl1	2.2007 (6)
Zn1—N2	2.0911 (14)	Zn1—Cl2	2.2219 (6)

N1—Zn1—N2	80.58 (6)	N1—Zn1—Cl2	110.66 (4)
N1—Zn1—Cl1	113.27 (4)	N2—Zn1—Cl2	108.06 (4)
N2—Zn1—Cl1	120.54 (4)	Cl1—Zn1—Cl2	117.82 (2)

Acknowledgements

We are grateful to Mrs Li for her assistance with the X-ray crystallographic analysis.

References

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