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

Li, H.; Hu, T.Q.; Zhang, S.G.

doi:10.1107/S160053680801180X

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page m771

doi:10.1107/S160053680801180X

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

Hong Li,^a ^* Tai Qiu Hu ^b and Shi Guo Zhang ^a

^aDepartment of Chemistry and Chemical Engineering, Institute of Materials Chemistry, Binzhou University, Binzhou 256603, People's Republic of China, and ^bDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
^*Correspondence e-mail: honglizhang1968@yahoo.cn

(Received 15 March 2008; accepted 24 April 2008; online 3 May 2008)

There are two molecules of the title complex, [ZnCl₂(C₁₃H₁₀N₂O)], in the asymmetric unit. Each Zn atom assumes a distorted tetrahedral ZnN₂Cl₂ coordination geometry. There are weak π–π stacking interactions between adjacent 1,10-phenanthroline rings [centroid–centroid distances = 3.6356 (18) and 3.6353 (18) Å].

Related literature

For a related structure, see: Zheng et al. (2003 ).

Experimental

Crystal data

[ZnCl₂(C₁₃H₁₀N₂O)]
M_r = 346.50
Triclinic, $[P \overline 1]$
a = 9.9051 (17) Å
b = 11.5654 (19) Å
c = 12.774 (2) Å
α = 91.849 (2)°
β = 108.295 (2)°
γ = 98.672 (2)°
V = 1368.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.18 mm⁻¹
T = 173 (2) K
0.51 × 0.40 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.403, T_max = 0.812
7507 measured reflections
5264 independent reflections
4386 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.05
5264 reflections
345 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cl1—Zn2	2.1911 (8)
Cl2—Zn2	2.2139 (9)
Cl3—Zn1	2.1949 (8)
Cl4—Zn1	2.2315 (8)
N1—Zn1	2.054 (2)
N2—Zn1	2.076 (2)
N3—Zn2	2.098 (2)
N4—Zn2	2.056 (2)

N1—Zn1—N2	81.15 (8)
N1—Zn1—Cl3	119.22 (6)
N2—Zn1—Cl3	114.55 (7)
N1—Zn1—Cl4	113.92 (6)
N2—Zn1—Cl4	107.63 (6)
Cl3—Zn1—Cl4	115.13 (3)
N4—Zn2—N3	80.57 (9)
N4—Zn2—Cl1	116.23 (7)
N3—Zn2—Cl1	117.56 (7)
N4—Zn2—Cl2	116.69 (7)
N3—Zn2—Cl2	104.48 (7)
Cl1—Zn2—Cl2	115.82 (4)

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801180X/ww2117sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801180X/ww2117Isup2.hkl

checkCIF report

Comment top

The derivatives of 1,10-phenanthroline play a pivotal role in the area of modern coordination chemistry (Zheng et al., 2003), but the complexes with 2-methoxy-1,10-phenanthroline as ligand has not been reported. We are interested in this kind of ligands and here we report a new complex (I) with 2-methoxy-1,10-phenanthroline as ligand.

The coordination structure of (I) is shown in Fig. 1. Each Zn(II) ion is coordinated with two Cl ions and two N atoms, and Zn—Cl bond lengths range from 2.1911 (8)Å to 2.2315 (8) Å and Zn—N bond lengths vary from 2.054 (2) Å to 2.098 (2)Å. Obviously Zn1 and Zn2 atoms are in a distorted tetrahedral geometry (Table 1). There are weak π-π stacking interaction between neighbouring 1,10-phenanthroline ligands. The centroid-to-centroid distances and the centroid-to-plane distances are Cg1···Cg2ⁱ = 3.6356 (18)Å and Cg1···Cg2ⁱ_perp = 3.476 Å; Cg3···Cg4ⁱⁱ = 3.6353 (18)Å and Cg3···Cg4ⁱ_perp = 3.434Å, and Cgi···Cgj should be the centroid-to-centroid distance while the Cgi···Cgj_prep should be the centroid-to-plane distance. Cg1, Cg2, Cg3 and Cg4 are the centroids of the rings N3/C14-C18, C17-C22, N2/C7-C11 and C5-C7/C11-C13, respectively. [symmetry codes: (i) 2-X, 2-Y, 2-Z; (ii) 1-X,1-Y,1-Z]

Related literature top

For a related structure, see: Zheng et al. (2003).

Experimental top

A methanol solution (10 ml) of ZnCl₂ (0.0785 g, 0.576 mmol) was added into 10 ml of methanol solution containing 2-methoxy-1,10-phenanthroline (0.1205 g, 0.573 mmol), and the mixed solution was stirred for a few minutes. Colorless crystals were obtained after the solution had been allowed to stand at room temperature for one week.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of complex (I), showing the the atom numbering scheme with thermal ellipsoids drawn at the 30% probability level.

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

Crystal data top

[ZnCl₂(C₁₃H₁₀N₂O)]	Z = 4
M_r = 346.50	F(000) = 696
Triclinic, P1	D_x = 1.682 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9051 (17) Å	Cell parameters from 3641 reflections
b = 11.5654 (19) Å	θ = 2.4–27.0°
c = 12.774 (2) Å	µ = 2.18 mm⁻¹
α = 91.849 (2)°	T = 173 K
β = 108.295 (2)°	Block, colorless
γ = 98.672 (2)°	0.51 × 0.40 × 0.10 mm
V = 1368.5 (4) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	5264 independent reflections
Radiation source: fine-focus sealed tube	4386 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→10
T_min = 0.403, T_max = 0.812	k = −14→12
7507 measured reflections	l = −15→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0513P)²] where P = (F_o² + 2F_c²)/3
5264 reflections	(Δ/σ)_max = 0.001
345 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[ZnCl₂(C₁₃H₁₀N₂O)]	γ = 98.672 (2)°
M_r = 346.50	V = 1368.5 (4) Å³
Triclinic, P1	Z = 4
a = 9.9051 (17) Å	Mo Kα radiation
b = 11.5654 (19) Å	µ = 2.18 mm⁻¹
c = 12.774 (2) Å	T = 173 K
α = 91.849 (2)°	0.51 × 0.40 × 0.10 mm
β = 108.295 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	5264 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4386 reflections with I > 2σ(I)
T_min = 0.403, T_max = 0.812	R_int = 0.019
7507 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.05	Δρ_max = 0.59 e Å⁻³
5264 reflections	Δρ_min = −0.35 e Å⁻³
345 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	0.5226 (3)	0.3267 (3)	1.0172 (2)	0.0481 (7)
H1A	0.5587	0.2596	0.9974	0.072*
H1B	0.4565	0.3028	1.0567	0.072*
H1C	0.6016	0.3835	1.0634	0.072*
C2	0.5263 (3)	0.4341 (2)	0.8608 (2)	0.0368 (6)
C3	0.6781 (3)	0.4562 (2)	0.8936 (2)	0.0462 (7)
H3	0.7326	0.4304	0.9593	0.055*
C4	0.7431 (3)	0.5151 (3)	0.8286 (3)	0.0505 (7)
H4	0.8433	0.5282	0.8487	0.061*
C5	0.6615 (3)	0.5573 (2)	0.7302 (2)	0.0429 (6)
C6	0.5121 (3)	0.5345 (2)	0.7051 (2)	0.0334 (5)
C7	0.4210 (3)	0.5801 (2)	0.6104 (2)	0.0370 (6)
C8	0.1928 (4)	0.6050 (3)	0.5073 (2)	0.0518 (7)
H8	0.0938	0.5918	0.4950	0.062*
C9	0.2462 (4)	0.6718 (3)	0.4356 (3)	0.0622 (9)
H9	0.1838	0.7031	0.3772	0.075*
C10	0.3897 (4)	0.6909 (3)	0.4518 (2)	0.0581 (9)
H10	0.4259	0.7341	0.4034	0.070*
C11	0.4844 (3)	0.6458 (2)	0.5413 (2)	0.0453 (7)
C12	0.6372 (4)	0.6614 (3)	0.5662 (3)	0.0540 (8)
H12	0.6791	0.7013	0.5191	0.065*
C13	0.7222 (3)	0.6196 (3)	0.6564 (3)	0.0518 (8)
H13	0.8215	0.6315	0.6707	0.062*
C14	0.7048 (3)	0.9284 (3)	1.0543 (2)	0.0493 (7)
H14	0.6289	0.9633	1.0609	0.059*
C15	0.7847 (4)	0.8771 (3)	1.1450 (2)	0.0577 (8)
H15	0.7612	0.8760	1.2100	0.069*
C16	0.8981 (4)	0.8284 (3)	1.1366 (2)	0.0593 (9)
H16	0.9532	0.7941	1.1966	0.071*
C17	0.9327 (3)	0.8296 (2)	1.0379 (2)	0.0463 (7)
C18	0.8429 (3)	0.8819 (2)	0.9508 (2)	0.0396 (6)
C19	0.8719 (3)	0.8864 (2)	0.8467 (2)	0.0388 (6)
C20	0.9915 (3)	0.8434 (2)	0.8365 (3)	0.0474 (7)
C21	1.0808 (4)	0.7921 (3)	0.9269 (3)	0.0642 (9)
H21	1.1610	0.7640	0.9198	0.077*
C22	1.0512 (4)	0.7837 (3)	1.0217 (3)	0.0628 (9)
H22	1.1092	0.7472	1.0784	0.075*
C23	1.0158 (4)	0.8553 (3)	0.7330 (3)	0.0594 (9)
H23	1.0949	0.8294	0.7215	0.071*
C24	0.9236 (3)	0.9045 (3)	0.6509 (3)	0.0526 (8)
H24	0.9398	0.9134	0.5834	0.063*
C25	0.8042 (3)	0.9416 (3)	0.6693 (2)	0.0486 (7)
C26	0.7173 (5)	1.0057 (4)	0.4866 (3)	0.0829 (13)
H26A	0.8048	1.0594	0.4954	0.124*
H26B	0.6365	1.0377	0.4417	0.124*
H26C	0.7209	0.9322	0.4514	0.124*
Cl1	0.57382 (10)	1.15815 (7)	0.79281 (6)	0.0581 (2)
Cl2	0.40833 (9)	0.84139 (7)	0.75709 (6)	0.0574 (2)
Cl3	0.09774 (8)	0.51212 (8)	0.79552 (7)	0.0641 (2)
Cl4	0.12965 (8)	0.27076 (6)	0.60771 (5)	0.04690 (18)
N1	0.4460 (2)	0.47186 (17)	0.76905 (16)	0.0327 (5)
N2	0.2774 (2)	0.55965 (19)	0.59217 (17)	0.0393 (5)
N3	0.7313 (3)	0.93004 (19)	0.95981 (17)	0.0410 (5)
N4	0.7788 (3)	0.93342 (19)	0.76405 (17)	0.0398 (5)
O1	0.4488 (2)	0.37827 (16)	0.91786 (14)	0.0420 (4)
O2	0.7019 (3)	0.9874 (2)	0.59364 (16)	0.0640 (6)
Zn1	0.22524 (3)	0.44580 (3)	0.70131 (2)	0.03586 (10)
Zn2	0.60675 (3)	0.97534 (3)	0.80582 (2)	0.03979 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.060 (2)	0.0456 (17)	0.0352 (14)	0.0128 (14)	0.0073 (14)	0.0087 (12)
C2	0.0341 (14)	0.0349 (14)	0.0394 (14)	0.0070 (11)	0.0090 (12)	0.0005 (11)
C3	0.0316 (15)	0.0500 (17)	0.0519 (16)	0.0070 (13)	0.0066 (13)	0.0025 (14)
C4	0.0281 (15)	0.0530 (18)	0.0653 (19)	0.0035 (13)	0.0100 (14)	−0.0037 (15)
C5	0.0353 (15)	0.0393 (15)	0.0547 (16)	−0.0019 (12)	0.0205 (13)	−0.0073 (13)
C6	0.0312 (13)	0.0297 (13)	0.0395 (13)	0.0017 (10)	0.0141 (11)	−0.0043 (10)
C7	0.0424 (16)	0.0308 (13)	0.0391 (14)	0.0000 (11)	0.0186 (12)	−0.0025 (11)
C8	0.0515 (19)	0.0526 (18)	0.0488 (17)	0.0105 (15)	0.0111 (15)	0.0138 (14)
C9	0.079 (3)	0.059 (2)	0.0433 (17)	0.0102 (18)	0.0118 (17)	0.0194 (15)
C10	0.085 (3)	0.0454 (18)	0.0474 (17)	−0.0003 (17)	0.0303 (18)	0.0102 (14)
C11	0.0601 (19)	0.0333 (15)	0.0448 (15)	−0.0037 (13)	0.0258 (15)	−0.0006 (12)
C12	0.066 (2)	0.0428 (17)	0.0623 (19)	−0.0104 (15)	0.0430 (18)	−0.0056 (15)
C13	0.0414 (17)	0.0467 (17)	0.069 (2)	−0.0087 (13)	0.0290 (16)	−0.0081 (15)
C14	0.0555 (19)	0.0522 (18)	0.0388 (15)	0.0018 (14)	0.0164 (14)	0.0057 (13)
C15	0.067 (2)	0.062 (2)	0.0357 (15)	−0.0041 (17)	0.0111 (15)	0.0122 (14)
C16	0.064 (2)	0.0517 (19)	0.0446 (17)	−0.0045 (16)	−0.0010 (16)	0.0167 (14)
C17	0.0420 (17)	0.0342 (15)	0.0501 (16)	0.0008 (12)	−0.0008 (13)	0.0087 (13)
C18	0.0391 (15)	0.0284 (13)	0.0437 (15)	−0.0002 (11)	0.0054 (12)	0.0047 (11)
C19	0.0376 (15)	0.0285 (13)	0.0459 (15)	−0.0003 (11)	0.0105 (12)	−0.0006 (11)
C20	0.0379 (16)	0.0386 (15)	0.0631 (18)	0.0010 (12)	0.0155 (14)	−0.0026 (14)
C21	0.0428 (19)	0.057 (2)	0.089 (3)	0.0133 (15)	0.0128 (18)	0.0051 (19)
C22	0.050 (2)	0.055 (2)	0.071 (2)	0.0121 (16)	−0.0005 (17)	0.0122 (17)
C23	0.0453 (19)	0.055 (2)	0.081 (2)	0.0036 (15)	0.0288 (18)	−0.0119 (17)
C24	0.0534 (19)	0.0561 (19)	0.0530 (18)	−0.0024 (15)	0.0305 (16)	−0.0081 (15)
C25	0.0572 (19)	0.0431 (16)	0.0443 (16)	−0.0002 (14)	0.0191 (15)	−0.0010 (13)
C26	0.129 (4)	0.091 (3)	0.0415 (18)	0.026 (3)	0.040 (2)	0.0185 (18)
Cl1	0.0790 (6)	0.0437 (4)	0.0556 (4)	0.0216 (4)	0.0216 (4)	0.0094 (3)
Cl2	0.0496 (5)	0.0599 (5)	0.0557 (4)	0.0008 (4)	0.0103 (4)	0.0108 (4)
Cl3	0.0402 (4)	0.0903 (6)	0.0655 (5)	0.0121 (4)	0.0239 (4)	−0.0136 (4)
Cl4	0.0517 (4)	0.0443 (4)	0.0428 (4)	0.0004 (3)	0.0164 (3)	0.0023 (3)
N1	0.0269 (11)	0.0334 (11)	0.0367 (11)	0.0025 (9)	0.0100 (9)	0.0011 (9)
N2	0.0413 (13)	0.0374 (12)	0.0385 (12)	0.0046 (10)	0.0126 (10)	0.0066 (10)
N3	0.0437 (14)	0.0403 (13)	0.0373 (12)	0.0046 (10)	0.0118 (10)	0.0066 (10)
N4	0.0437 (13)	0.0415 (13)	0.0355 (11)	0.0063 (10)	0.0152 (10)	0.0038 (10)
O1	0.0366 (11)	0.0471 (11)	0.0419 (10)	0.0072 (8)	0.0113 (9)	0.0116 (9)
O2	0.0804 (17)	0.0825 (16)	0.0392 (11)	0.0287 (13)	0.0258 (11)	0.0171 (11)
Zn1	0.02763 (17)	0.04296 (19)	0.03691 (17)	0.00325 (13)	0.01139 (13)	0.00511 (13)
Zn2	0.0424 (2)	0.04270 (19)	0.03666 (18)	0.01284 (14)	0.01315 (15)	0.00795 (14)

Geometric parameters (Å, º) top

C1—O1	1.449 (3)	C15—H15	0.9300
C1—H1A	0.9600	C16—C17	1.406 (4)
C1—H1B	0.9600	C16—H16	0.9300
C1—H1C	0.9600	C17—C18	1.407 (4)
C2—N1	1.323 (3)	C17—C22	1.427 (5)
C2—O1	1.330 (3)	C18—N3	1.344 (4)
C2—C3	1.409 (4)	C18—C19	1.447 (4)
C3—C4	1.345 (4)	C19—N4	1.356 (3)
C3—H3	0.9300	C19—C20	1.392 (4)
C4—C5	1.411 (4)	C20—C23	1.423 (4)
C4—H4	0.9300	C20—C21	1.424 (4)
C5—C6	1.393 (4)	C21—C22	1.336 (5)
C5—C13	1.428 (4)	C21—H21	0.9300
C6—N1	1.361 (3)	C22—H22	0.9300
C6—C7	1.434 (4)	C23—C24	1.361 (5)
C7—N2	1.349 (3)	C23—H23	0.9300
C7—C11	1.412 (4)	C24—C25	1.400 (4)
C8—N2	1.323 (3)	C24—H24	0.9300
C8—C9	1.394 (4)	C25—N4	1.315 (3)
C8—H8	0.9300	C25—O2	1.349 (4)
C9—C10	1.353 (5)	C26—O2	1.441 (3)
C9—H9	0.9300	C26—H26A	0.9600
C10—C11	1.404 (4)	C26—H26B	0.9600
C10—H10	0.9300	C26—H26C	0.9600
C11—C12	1.427 (4)	Cl1—Zn2	2.1911 (8)
C12—C13	1.349 (5)	Cl2—Zn2	2.2139 (9)
C12—H12	0.9300	Cl3—Zn1	2.1949 (8)
C13—H13	0.9300	Cl4—Zn1	2.2315 (8)
C14—N3	1.313 (3)	N1—Zn1	2.054 (2)
C14—C15	1.389 (4)	N2—Zn1	2.076 (2)
C14—H14	0.9300	N3—Zn2	2.098 (2)
C15—C16	1.361 (5)	N4—Zn2	2.056 (2)

O1—C1—H1A	109.5	N3—C18—C19	117.8 (2)
O1—C1—H1B	109.5	C17—C18—C19	119.2 (3)
H1A—C1—H1B	109.5	N4—C19—C20	123.9 (3)
O1—C1—H1C	109.5	N4—C19—C18	116.8 (2)
H1A—C1—H1C	109.5	C20—C19—C18	119.3 (3)
H1B—C1—H1C	109.5	C19—C20—C23	115.8 (3)
N1—C2—O1	113.0 (2)	C19—C20—C21	119.9 (3)
N1—C2—C3	121.8 (2)	C23—C20—C21	124.3 (3)
O1—C2—C3	125.1 (2)	C22—C21—C20	121.0 (3)
C4—C3—C2	119.0 (3)	C22—C21—H21	119.5
C4—C3—H3	120.5	C20—C21—H21	119.5
C2—C3—H3	120.5	C21—C22—C17	121.5 (3)
C3—C4—C5	120.9 (3)	C21—C22—H22	119.3
C3—C4—H4	119.5	C17—C22—H22	119.3
C5—C4—H4	119.5	C24—C23—C20	120.2 (3)
C6—C5—C4	116.5 (3)	C24—C23—H23	119.9
C6—C5—C13	119.2 (3)	C20—C23—H23	119.9
C4—C5—C13	124.3 (3)	C23—C24—C25	119.1 (3)
N1—C6—C5	122.6 (2)	C23—C24—H24	120.5
N1—C6—C7	117.0 (2)	C25—C24—H24	120.5
C5—C6—C7	120.3 (2)	N4—C25—O2	112.3 (3)
N2—C7—C11	122.8 (3)	N4—C25—C24	122.7 (3)
N2—C7—C6	118.0 (2)	O2—C25—C24	125.0 (3)
C11—C7—C6	119.2 (3)	O2—C26—H26A	109.5
N2—C8—C9	122.5 (3)	O2—C26—H26B	109.5
N2—C8—H8	118.7	H26A—C26—H26B	109.5
C9—C8—H8	118.7	O2—C26—H26C	109.5
C10—C9—C8	119.4 (3)	H26A—C26—H26C	109.5
C10—C9—H9	120.3	H26B—C26—H26C	109.5
C8—C9—H9	120.3	C2—N1—C6	119.0 (2)
C9—C10—C11	120.3 (3)	C2—N1—Zn1	128.98 (18)
C9—C10—H10	119.8	C6—N1—Zn1	111.96 (16)
C11—C10—H10	119.8	C8—N2—C7	118.5 (2)
C10—C11—C7	116.4 (3)	C8—N2—Zn1	130.2 (2)
C10—C11—C12	124.8 (3)	C7—N2—Zn1	111.08 (17)
C7—C11—C12	118.8 (3)	C14—N3—C18	118.5 (2)
C13—C12—C11	121.6 (3)	C14—N3—Zn2	129.7 (2)
C13—C12—H12	119.2	C18—N3—Zn2	111.10 (17)
C11—C12—H12	119.2	C25—N4—C19	118.4 (3)
C12—C13—C5	120.8 (3)	C25—N4—Zn2	128.8 (2)
C12—C13—H13	119.6	C19—N4—Zn2	112.72 (17)
C5—C13—H13	119.6	C2—O1—C1	118.9 (2)
N3—C14—C15	123.2 (3)	C25—O2—C26	118.9 (3)
N3—C14—H14	118.4	N1—Zn1—N2	81.15 (8)
C15—C14—H14	118.4	N1—Zn1—Cl3	119.22 (6)
C16—C15—C14	118.5 (3)	N2—Zn1—Cl3	114.55 (7)
C16—C15—H15	120.7	N1—Zn1—Cl4	113.92 (6)
C14—C15—H15	120.7	N2—Zn1—Cl4	107.63 (6)
C15—C16—C17	120.5 (3)	Cl3—Zn1—Cl4	115.13 (3)
C15—C16—H16	119.7	N4—Zn2—N3	80.57 (9)
C17—C16—H16	119.7	N4—Zn2—Cl1	116.23 (7)
C16—C17—C18	116.1 (3)	N3—Zn2—Cl1	117.56 (7)
C16—C17—C22	124.9 (3)	N4—Zn2—Cl2	116.69 (7)
C18—C17—C22	119.1 (3)	N3—Zn2—Cl2	104.48 (7)
N3—C18—C17	123.0 (3)	Cl1—Zn2—Cl2	115.82 (4)

N1—C2—C3—C4	−1.5 (4)	O1—C2—N1—Zn1	−4.6 (3)
O1—C2—C3—C4	−179.2 (3)	C3—C2—N1—Zn1	177.47 (19)
C2—C3—C4—C5	1.7 (4)	C5—C6—N1—C2	2.3 (4)
C3—C4—C5—C6	0.0 (4)	C7—C6—N1—C2	−176.0 (2)
C3—C4—C5—C13	−179.4 (3)	C5—C6—N1—Zn1	−175.99 (19)
C4—C5—C6—N1	−2.0 (4)	C7—C6—N1—Zn1	5.7 (3)
C13—C5—C6—N1	177.4 (2)	C9—C8—N2—C7	0.7 (4)
C4—C5—C6—C7	176.2 (2)	C9—C8—N2—Zn1	−173.7 (2)
C13—C5—C6—C7	−4.3 (4)	C11—C7—N2—C8	−1.4 (4)
N1—C6—C7—N2	1.0 (3)	C6—C7—N2—C8	177.6 (2)
C5—C6—C7—N2	−177.3 (2)	C11—C7—N2—Zn1	174.0 (2)
N1—C6—C7—C11	−180.0 (2)	C6—C7—N2—Zn1	−7.1 (3)
C5—C6—C7—C11	1.6 (4)	C15—C14—N3—C18	−1.4 (4)
N2—C8—C9—C10	0.6 (5)	C15—C14—N3—Zn2	168.3 (2)
C8—C9—C10—C11	−1.3 (5)	C17—C18—N3—C14	0.1 (4)
C9—C10—C11—C7	0.6 (4)	C19—C18—N3—C14	−179.0 (2)
C9—C10—C11—C12	−179.6 (3)	C17—C18—N3—Zn2	−171.4 (2)
N2—C7—C11—C10	0.7 (4)	C19—C18—N3—Zn2	9.5 (3)
C6—C7—C11—C10	−178.2 (2)	O2—C25—N4—C19	178.6 (2)
N2—C7—C11—C12	−179.1 (2)	C24—C25—N4—C19	−0.5 (4)
C6—C7—C11—C12	2.0 (4)	O2—C25—N4—Zn2	2.1 (4)
C10—C11—C12—C13	177.2 (3)	C24—C25—N4—Zn2	−177.0 (2)
C7—C11—C12—C13	−3.0 (4)	C20—C19—N4—C25	−1.6 (4)
C11—C12—C13—C5	0.3 (5)	C18—C19—N4—C25	178.2 (2)
C6—C5—C13—C12	3.3 (4)	C20—C19—N4—Zn2	175.5 (2)
C4—C5—C13—C12	−177.2 (3)	C18—C19—N4—Zn2	−4.7 (3)
N3—C14—C15—C16	1.6 (5)	N1—C2—O1—C1	176.7 (2)
C14—C15—C16—C17	−0.4 (5)	C3—C2—O1—C1	−5.4 (4)
C15—C16—C17—C18	−0.7 (4)	N4—C25—O2—C26	177.9 (3)
C15—C16—C17—C22	178.3 (3)	C24—C25—O2—C26	−3.1 (5)
C16—C17—C18—N3	0.9 (4)	C2—N1—Zn1—N2	174.7 (2)
C22—C17—C18—N3	−178.2 (3)	C6—N1—Zn1—N2	−7.20 (16)
C16—C17—C18—C19	180.0 (2)	C2—N1—Zn1—Cl3	61.5 (2)
C22—C17—C18—C19	0.9 (4)	C6—N1—Zn1—Cl3	−120.45 (15)
N3—C18—C19—N4	−3.5 (4)	C2—N1—Zn1—Cl4	−79.8 (2)
C17—C18—C19—N4	177.4 (2)	C6—N1—Zn1—Cl4	98.24 (15)
N3—C18—C19—C20	176.4 (2)	C8—N2—Zn1—N1	−177.6 (3)
C17—C18—C19—C20	−2.7 (4)	C7—N2—Zn1—N1	7.67 (16)
N4—C19—C20—C23	2.3 (4)	C8—N2—Zn1—Cl3	−59.5 (3)
C18—C19—C20—C23	−177.5 (2)	C7—N2—Zn1—Cl3	125.84 (16)
N4—C19—C20—C21	−178.0 (3)	C8—N2—Zn1—Cl4	70.0 (3)
C18—C19—C20—C21	2.1 (4)	C7—N2—Zn1—Cl4	−104.74 (16)
C19—C20—C21—C22	0.5 (5)	C25—N4—Zn2—N3	−175.9 (3)
C23—C20—C21—C22	−179.9 (3)	C19—N4—Zn2—N3	7.41 (18)
C20—C21—C22—C17	−2.4 (5)	C25—N4—Zn2—Cl1	−59.7 (3)
C16—C17—C22—C21	−177.3 (3)	C19—N4—Zn2—Cl1	123.57 (17)
C18—C17—C22—C21	1.7 (5)	C25—N4—Zn2—Cl2	82.5 (2)
C19—C20—C23—C24	−1.0 (4)	C19—N4—Zn2—Cl2	−94.14 (18)
C21—C20—C23—C24	179.3 (3)	C14—N3—Zn2—N4	−179.4 (3)
C20—C23—C24—C25	−0.8 (5)	C18—N3—Zn2—N4	−9.09 (18)
C23—C24—C25—N4	1.6 (5)	C14—N3—Zn2—Cl1	65.8 (3)
C23—C24—C25—O2	−177.3 (3)	C18—N3—Zn2—Cl1	−123.84 (17)
O1—C2—N1—C6	177.4 (2)	C14—N3—Zn2—Cl2	−64.1 (3)
C3—C2—N1—C6	−0.5 (4)	C18—N3—Zn2—Cl2	106.21 (17)

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₃H₁₀N₂O)]
M_r	346.50
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.9051 (17), 11.5654 (19), 12.774 (2)
α, β, γ (°)	91.849 (2), 108.295 (2), 98.672 (2)
V (Å³)	1368.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.18
Crystal size (mm)	0.51 × 0.40 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.403, 0.812
No. of measured, independent and observed [I > 2σ(I)] reflections	7507, 5264, 4386
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.05
No. of reflections	5264
No. of parameters	345
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.35

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cl1—Zn2	2.1911 (8)	N1—Zn1	2.054 (2)
Cl2—Zn2	2.2139 (9)	N2—Zn1	2.076 (2)
Cl3—Zn1	2.1949 (8)	N3—Zn2	2.098 (2)
Cl4—Zn1	2.2315 (8)	N4—Zn2	2.056 (2)

N1—Zn1—N2	81.15 (8)	N4—Zn2—N3	80.57 (9)
N1—Zn1—Cl3	119.22 (6)	N4—Zn2—Cl1	116.23 (7)
N2—Zn1—Cl3	114.55 (7)	N3—Zn2—Cl1	117.56 (7)
N1—Zn1—Cl4	113.92 (6)	N4—Zn2—Cl2	116.69 (7)
N2—Zn1—Cl4	107.63 (6)	N3—Zn2—Cl2	104.48 (7)
Cl3—Zn1—Cl4	115.13 (3)	Cl1—Zn2—Cl2	115.82 (4)

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province of China for support (grant No. Y2007B26).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zheng, S.-L., Zhang, J.-P., Wong, W.-T. & Chen, X.-M. (2003). J. Am. Chem. Soc. 125, 6882–6883. Web of Science CSD CrossRef PubMed CAS Google Scholar