Di­chloro­bis­[2-(o-tolyl­iminio­methyl)­phenolato-O]­zinc(II)

In the mononuclear title compound, [ZnCl₂(C₁₄H₁₃NO)₂], the Zn^II ion is located on a twofold axis of the monoclinic space group so that the whole mol­ecule has a twofold symmetry. The Zn^II ion has a tetrahedral coordination consisting of two chlorine ions and the O atoms of the ligands. The coordination angles around zinc have values between 102.89 (8) (O-Zn-O) and 115.83 (5)° (Cl-Zn-O). The Zn-O and Zn-Cl bond lengths are 1.977 (2) and 2.2401 (7) Å, respectively. There are intra- and intermolecular hydrogen bonds in the structure.

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1993); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: Sir in MolEN; program(s) used to refine structure: LSFM in MolEN; molecular graphics: PLATON99 (Spek, 1999); software used to prepare material for publication: MolEN.

(I)

Crystal data

[ZnCl2(C14H13NO)2]	Z = 4
Mr = 558.81	Dx = 1.450 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 16.0495 (11) Å	θ = 11.8–21.0°
b = 10.5240 (13) Å	µ = 1.20 mm^−1
c = 15.6324 (12) Å	T = 295 K
β = 104.232 (2)°	Prism, yellow
V = 2559.4 (4) Å^3	0.35 × 0.25 × 0.15 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.010
ω/2θ scans	θmax = 25.3°
Absorption correction: ψ scan empirical (using intensity measurements) via ψ scans (Fair, 1990)	h = −18→19
Tmin = 0.694, Tmax = 0.836	k = −12→0
2565 measured reflections	l = −18→0
2467 independent reflections	3 standard reflections every 120 min
1929 reflections with I > 3σ(I)	intensity decay: 1.8%

Refinement

Refinement on F	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.028	weight: w = 1/[σF^2 + (0.02F)^2 + 0.4] except w = 0 if F^2 < cutoff.σF^2, where cutoff is 3.0
wR(F^2) = 0.037	(Δ/σ)max = 0.00025
S = 1.04	Δρmax = 0.27 e Å^−3
1929 reflections	Δρmin = −0.19 e Å^−3
159 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn	0.500	0.07524 (4)	0.250	0.0419 (1)
Cl	0.61546 (4)	0.19710 (7)	0.25456 (4)	0.0574 (2)
O1	0.5326 (1)	−0.0419 (2)	0.3517 (1)	0.0458 (4)
N1	0.6548 (1)	−0.0923 (2)	0.4908 (1)	0.0388 (5)
C1	0.4791 (1)	−0.1045 (2)	0.3873 (2)	0.0407 (6)
C2	0.3926 (2)	−0.1265 (3)	0.3432 (2)	0.0522 (6)
C3	0.3382 (2)	−0.1893 (3)	0.3840 (2)	0.0584 (8)
C4	0.3658 (2)	−0.2329 (3)	0.4703 (2)	0.0543 (6)
C5	0.4495 (1)	−0.2158 (2)	0.5149 (2)	0.0457 (6)
C6	0.5079 (1)	−0.1532 (2)	0.4747 (1)	0.0375 (6)
C7	0.5951 (1)	−0.1435 (2)	0.5225 (1)	0.0394 (6)
C8	0.7439 (1)	−0.0838 (2)	0.5332 (2)	0.0416 (6)
C9	0.7724 (2)	−0.0957 (3)	0.6239 (2)	0.0579 (8)
C10	0.8592 (2)	−0.0893 (3)	0.6633 (2)	0.0703 (10)
C11	0.9167 (2)	−0.0678 (3)	0.6126 (2)	0.0693 (10)
C12	0.8877 (2)	−0.0553 (3)	0.5231 (2)	0.0575 (8)
C13	0.8013 (2)	−0.0633 (2)	0.4806 (2)	0.0452 (6)
C14	0.7709 (2)	−0.0503 (3)	0.3819 (2)	0.0626 (8)
H1	0.637	−0.057	0.433	0.0507*
H2	0.372	−0.098	0.284	0.0684*
H3	0.280	−0.203	0.353	0.0760*
H4	0.327	−0.275	0.498	0.0722*
H5	0.469	−0.246	0.574	0.0608*
H7	0.611	−0.176	0.581	0.0519*
H9	0.732	−0.110	0.659	0.0773*
H10	0.879	−0.098	0.725	0.0925*
H11	0.976	−0.062	0.640	0.0887*
H12	0.928	−0.041	0.489	0.0773*
H141	0.717	−0.009	0.367	0.0823*
H142	0.812	−0.002	0.361	0.0823*
H143	0.766	−0.132	0.356	0.0823*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn	0.0322 (2)	0.0573 (2)	0.0347 (2)	0	0.0051 (1)	0
Cl	0.0425 (3)	0.0744 (4)	0.0540 (3)	−0.0146 (3)	0.0094 (2)	−0.0044 (3)
O1	0.0325 (7)	0.0634 (9)	0.0392 (7)	−0.0025 (7)	0.0042 (6)	0.0071 (7)
N1	0.0276 (8)	0.046 (1)	0.0400 (9)	0.0015 (7)	0.0031 (7)	0.0005 (8)
C1	0.034 (1)	0.042 (1)	0.044 (1)	−0.0002 (9)	0.0057 (9)	−0.0060 (9)
C2	0.037 (1)	0.063 (1)	0.049 (1)	−0.005 (1)	−0.004 (1)	−0.001 (1)
C3	0.031 (1)	0.057 (1)	0.080 (2)	−0.009 (1)	−0.000 (1)	−0.005 (1)
C4	0.038 (1)	0.052 (1)	0.075 (1)	−0.007 (1)	0.018 (1)	0.002 (1)
C5	0.039 (1)	0.044 (1)	0.055 (1)	−0.001 (1)	0.0135 (9)	0.002 (1)
C6	0.0302 (9)	0.040 (1)	0.041 (1)	0.0016 (9)	0.0063 (8)	−0.0033 (9)
C7	0.035 (1)	0.042 (1)	0.039 (1)	0.0031 (9)	0.0049 (8)	0.0009 (9)
C8	0.0287 (9)	0.041 (1)	0.051 (1)	0.0030 (9)	0.0019 (9)	−0.002 (1)
C9	0.037 (1)	0.079 (2)	0.053 (1)	0.002 (1)	0.002 (1)	−0.002 (1)
C10	0.044 (1)	0.096 (2)	0.059 (2)	0.001 (1)	−0.010 (1)	−0.005 (2)
C11	0.031 (1)	0.078 (2)	0.087 (2)	0.001 (1)	−0.008 (1)	0.001 (2)
C12	0.031 (1)	0.056 (1)	0.084 (2)	0.000 (1)	0.011 (1)	0.009 (1)
C13	0.034 (1)	0.039 (1)	0.061 (1)	0.0009 (9)	0.0089 (9)	0.003 (1)
C14	0.044 (1)	0.084 (2)	0.062 (1)	0.000 (1)	0.017 (1)	0.010 (1)

Geometric parameters (Å, º)

Zn—Cl	2.2401 (7)	C6—C7	1.418 (3)
Zn—O1	1.977 (2)	C7—H7	0.95
O1—C1	1.311 (3)	C8—C9	1.384 (4)
N1—C7	1.299 (3)	C8—C13	1.395 (4)
N1—C8	1.423 (3)	C9—C10	1.379 (4)
N1—H1	0.95	C9—H9	0.95
C1—C2	1.409 (3)	C10—C11	1.375 (5)
C1—C6	1.426 (3)	C10—H10	0.95
C2—C3	1.371 (4)	C11—C12	1.368 (5)
C2—H2	0.95	C11—H11	0.95
C3—C4	1.390 (4)	C12—C13	1.384 (3)
C3—H3	0.95	C12—H12	0.95
C4—C5	1.364 (3)	C13—C14	1.506 (4)
C4—H4	0.95	C14—H141	0.95
C5—C6	1.414 (3)	C14—H142	0.95
C5—H5	0.95	C14—H143	0.95
Cl—Zn—O1	106.14 (5)	N1—C7—C6	123.6 (2)
Cl—Zn—Cl^i	110.16 (3)	N1—C7—H7	117.9
Cl—Zn—O1^i	115.83 (5)	C6—C7—H7	118.5
Cl^i—Zn—O1	115.83 (5)	N1—C8—C9	120.9 (2)
O1—Zn—O1^i	102.89 (8)	N1—C8—C13	118.0 (2)
Cl^i—Zn—O1^i	106.14 (5)	C9—C8—C13	121.2 (2)
Zn—O1—C1	125.7 (1)	C8—C9—C10	119.8 (3)
C7—N1—C8	126.8 (2)	C8—C9—H9	120.0
C7—N1—H1	116.6	C10—C9—H9	120.2
C8—N1—H1	116.6	C9—C10—C11	119.9 (3)
O1—C1—C2	123.0 (2)	C9—C10—H10	120.4
O1—C1—C6	119.7 (2)	C11—C10—H10	119.7
C2—C1—C6	117.3 (2)	C10—C11—C12	119.8 (2)
C1—C2—C3	121.0 (2)	C10—C11—H11	120.0
C1—C2—H2	119.3	C12—C11—H11	120.2
C3—C2—H2	119.7	C11—C12—C13	122.3 (3)
C2—C3—C4	121.5 (2)	C11—C12—H12	119.2
C2—C3—H3	119.0	C13—C12—H12	118.6
C4—C3—H3	119.5	C8—C13—C12	117.1 (2)
C3—C4—C5	119.5 (3)	C8—C13—C14	121.6 (2)
C3—C4—H4	120.2	C12—C13—C14	121.3 (3)
C5—C4—H4	120.3	C13—C14—H141	109.8
C4—C5—C6	120.8 (2)	C13—C14—H142	109.3
C4—C5—H5	120.0	C13—C14—H143	109.4
C6—C5—H5	119.2	H141—C14—H142	109.5
C1—C6—C5	119.9 (2)	H141—C14—H143	109.5
C1—C6—C7	121.7 (2)	H142—C14—H143	109.5
C5—C6—C7	118.4 (2)
Cl—Zn—O1—C1	160.6 (2)	H5—C5—C6—C1	−178.6
Cl^i—Zn—O1—C1	38.0 (2)	C1—C6—C7—H7	179.0
O1^i—Zn—O1—C1	−77.3 (2)	C5—C6—C7—N1	177.4 (2)
Zn—O1—C1—C2	19.3 (3)	N1—C8—C9—C10	178.9 (3)
Zn—O1—C1—C6	−160.4 (2)	C13—C8—C9—H9	−179.6
C8—N1—C7—C6	−177.2 (2)	N1—C8—C13—C12	−180.0 (3)
H1—N1—C7—H7	−177.3	C9—C8—C13—C14	179.9 (3)
C7—N1—C8—C9	−19.9 (4)	C8—C9—C10—H10	−179.3
C7—N1—C8—C13	160.0 (2)	H9—C9—C10—C11	−179.7
H1—N1—C8—C9	160.0	C9—C10—C11—H11	179.1
H1—N1—C8—C13	−20.1	H10—C10—C11—C12	179.7
O1—C1—C2—C3	−178.1 (2)	C10—C11—C12—H12	−179.9
C6—C1—C2—H2	−177.8	H11—C11—C12—C13	179.8
O1—C1—C6—C5	177.1 (2)	C11—C12—C13—C14	−179.5 (3)
C2—C1—C6—C7	175.8 (2)	H12—C12—C13—C8	−179.4
C1—C2—C3—H3	−179.9	C8—C13—C14—H141	34.5
H2—C2—C3—C4	179.9	C8—C13—C14—H142	154.5
C2—C3—C4—H4	178.7	C8—C13—C14—H143	−85.6
H3—C3—C4—C5	178.7	C12—C13—C14—H141	−145.5
C3—C4—C5—H5	−179.2	C12—C13—C14—H142	−25.4
H4—C4—C5—C6	−179.7	C12—C13—C14—H143	94.3
C4—C5—C6—C7	−177.0 (2)

Symmetry code: (i) −x+1, y, −z+1/2.