Dichlorido{2-[(2-isopropyl-ammonio-ethyl)imino-meth-yl]-5-methoxy-phenolato}zinc(II).

The Zn(II) atom in the title compound, [ZnCl(2)(C(13)H(20)N(2)O(2))], is four-coordinated by the imine N and phenolate O atoms of the zwitterionic Schiff base ligand, and by two choride ions in a distorted tetra-hedral coordination. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O and N-H⋯Cl hydrogen bonds along [010].

Related literature

For a nickel(II) complex with the 3-ethoxy­salicylaldehyde ligand, see: Han (2008 ▶). For similar zinc(II) complexes with Schiff bases, see: Ali et al. (2008 ▶); Wang (2007 ▶); Zhang et al. (2008 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

[ZnCl2(C13H20N2O2)]

M = 372.58

Monoclinic,

a = 6.2915 (9) Å

b = 11.8990 (18) Å

c = 22.115 (4) Å

β = 96.518 (4)°

V = 1644.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.82 mm−1

T = 298 K

0.18 × 0.18 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.735, T max = 0.735

9437 measured reflections

3557 independent reflections

2515 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.086

S = 1.01

3557 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001127X/bx2273sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001127X/bx2273Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[ZnCl2(C13H20N2O2)]	F(000) = 768
Mr = 372.58	Dx = 1.504 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.2915 (9) Å	Cell parameters from 1935 reflections
b = 11.8990 (18) Å	θ = 2.5–24.5°
c = 22.115 (4) Å	µ = 1.82 mm−1
β = 96.518 (4)°	T = 298 K
V = 1644.9 (4) Å3	Block, colourless
Z = 4	0.18 × 0.18 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	3557 independent reflections
Radiation source: fine-focus sealed tube	2515 reflections with I > 2σ(I)
graphite	Rint = 0.042
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
Tmin = 0.735, Tmax = 0.735	k = −13→15
9437 measured reflections	l = −27→28

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0339P)2 + 0.3384P] where P = (Fo2 + 2Fc2)/3
3557 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq
Zn1	0.75702 (6)	0.83340 (3)	0.763592 (16)	0.03646 (12)
Cl1	0.56343 (14)	0.81826 (7)	0.67166 (4)	0.0519 (2)
Cl2	1.00002 (12)	0.97048 (6)	0.77248 (4)	0.0497 (2)
N1	0.8725 (4)	0.68364 (18)	0.79167 (11)	0.0336 (6)
N2	0.9034 (4)	0.58914 (18)	0.66336 (10)	0.0329 (6)
H2A	0.7788	0.5959	0.6794	0.039*
H2B	0.9412	0.5162	0.6658	0.039*
O1	0.5732 (3)	0.85623 (15)	0.82740 (9)	0.0399 (5)
O2	0.0900 (4)	0.7411 (2)	0.95938 (11)	0.0652 (7)
C1	0.6016 (5)	0.6635 (2)	0.86232 (13)	0.0360 (7)
C2	0.5081 (5)	0.7727 (2)	0.85973 (13)	0.0336 (7)
C3	0.3364 (5)	0.7916 (2)	0.89406 (14)	0.0397 (7)
H3	0.2735	0.8625	0.8931	0.048*
C4	0.2582 (5)	0.7086 (3)	0.92900 (14)	0.0449 (8)
C5	0.3475 (6)	0.6021 (3)	0.93171 (16)	0.0524 (9)
H5	0.2956	0.5460	0.9554	0.063*
C6	0.5158 (5)	0.5815 (3)	0.89822 (15)	0.0483 (8)
H6	0.5752	0.5099	0.8995	0.058*
C7	0.7806 (5)	0.6282 (2)	0.83109 (13)	0.0367 (7)
H7	0.8353	0.5571	0.8408	0.044*
C8	1.0626 (5)	0.6333 (3)	0.76875 (14)	0.0417 (8)
H8A	1.0622	0.5528	0.7758	0.050*
H8B	1.1907	0.6640	0.7913	0.050*
C9	1.0685 (5)	0.6552 (2)	0.70159 (14)	0.0374 (7)
H9A	1.0454	0.7346	0.6935	0.045*
H9B	1.2089	0.6358	0.6906	0.045*
C10	0.8660 (6)	0.6211 (3)	0.59723 (15)	0.0513 (9)
H10	0.8115	0.6983	0.5952	0.062*
C11	0.6940 (6)	0.5472 (3)	0.56592 (17)	0.0732 (12)
H11A	0.7428	0.4707	0.5669	0.110*
H11B	0.6613	0.5709	0.5244	0.110*
H11C	0.5679	0.5526	0.5864	0.110*
C12	1.0658 (7)	0.6201 (4)	0.56802 (18)	0.0780 (13)
H12A	1.1282	0.5465	0.5715	0.117*
H12B	1.1643	0.6738	0.5878	0.117*
H12C	1.0346	0.6394	0.5258	0.117*
C13	0.0014 (7)	0.6613 (3)	0.99717 (18)	0.0725 (12)
H13A	−0.0495	0.5974	0.9732	0.109*
H13B	−0.1155	0.6949	1.0150	0.109*
H13C	0.1092	0.6376	1.0288	0.109*

	U11	U22	U33	U12	U13	U23
Zn1	0.0419 (2)	0.02734 (18)	0.0413 (2)	0.00185 (15)	0.00994 (15)	−0.00074 (15)
Cl1	0.0564 (5)	0.0489 (5)	0.0486 (5)	0.0057 (4)	−0.0021 (4)	−0.0049 (4)
Cl2	0.0413 (5)	0.0393 (4)	0.0687 (6)	−0.0057 (4)	0.0072 (4)	0.0064 (4)
N1	0.0342 (14)	0.0289 (13)	0.0369 (14)	0.0010 (10)	0.0005 (11)	−0.0047 (10)
N2	0.0353 (14)	0.0291 (12)	0.0351 (14)	0.0002 (10)	0.0076 (11)	−0.0013 (10)
O1	0.0491 (13)	0.0260 (10)	0.0477 (13)	0.0021 (9)	0.0186 (11)	0.0011 (9)
O2	0.0748 (18)	0.0618 (15)	0.0661 (17)	−0.0106 (13)	0.0389 (15)	−0.0050 (13)
C1	0.0391 (17)	0.0321 (15)	0.0365 (17)	−0.0011 (13)	0.0028 (13)	−0.0009 (13)
C2	0.0367 (17)	0.0316 (16)	0.0320 (17)	−0.0050 (13)	0.0018 (13)	−0.0046 (13)
C3	0.0457 (19)	0.0347 (16)	0.0399 (18)	−0.0030 (14)	0.0095 (15)	−0.0069 (14)
C4	0.047 (2)	0.051 (2)	0.0370 (18)	−0.0116 (16)	0.0082 (15)	−0.0074 (15)
C5	0.061 (2)	0.048 (2)	0.050 (2)	−0.0107 (17)	0.0151 (18)	0.0073 (16)
C6	0.055 (2)	0.0361 (17)	0.054 (2)	−0.0002 (15)	0.0057 (18)	0.0081 (15)
C7	0.0444 (18)	0.0255 (14)	0.0384 (18)	0.0035 (13)	−0.0035 (15)	−0.0021 (13)
C8	0.0338 (17)	0.0439 (18)	0.046 (2)	0.0068 (14)	0.0002 (14)	−0.0072 (14)
C9	0.0297 (15)	0.0320 (16)	0.051 (2)	−0.0015 (13)	0.0076 (14)	−0.0029 (14)
C10	0.069 (2)	0.0459 (19)	0.039 (2)	0.0039 (18)	0.0056 (18)	0.0044 (15)
C11	0.085 (3)	0.084 (3)	0.046 (2)	−0.011 (2)	−0.014 (2)	−0.005 (2)
C12	0.085 (3)	0.095 (3)	0.058 (3)	0.002 (3)	0.025 (2)	0.011 (2)
C13	0.082 (3)	0.080 (3)	0.062 (3)	−0.020 (2)	0.035 (2)	0.000 (2)

Zn1—O1	1.9425 (19)	C5—H5	0.9300
Zn1—N1	1.997 (2)	C6—H6	0.9300
Zn1—Cl2	2.2290 (9)	C7—H7	0.9300
Zn1—Cl1	2.2554 (10)	C8—C9	1.513 (4)
N1—C7	1.282 (3)	C8—H8A	0.9700
N1—C8	1.478 (3)	C8—H8B	0.9700
N2—C9	1.487 (4)	C9—H9A	0.9700
N2—C10	1.504 (4)	C9—H9B	0.9700
N2—H2A	0.9000	C10—C12	1.477 (5)
N2—H2B	0.9000	C10—C11	1.502 (5)
O1—C2	1.317 (3)	C10—H10	0.9800
O2—C4	1.372 (4)	C11—H11A	0.9600
O2—C13	1.420 (4)	C11—H11B	0.9600
C1—C6	1.404 (4)	C11—H11C	0.9600
C1—C2	1.425 (4)	C12—H12A	0.9600
C1—C7	1.448 (4)	C12—H12B	0.9600
C2—C3	1.408 (4)	C12—H12C	0.9600
C3—C4	1.379 (4)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.385 (4)	C13—H13C	0.9600
C5—C6	1.381 (4)
O1—Zn1—N1	97.16 (9)	C1—C7—H7	116.2
O1—Zn1—Cl2	107.02 (6)	N1—C8—C9	112.2 (2)
N1—Zn1—Cl2	113.82 (7)	N1—C8—H8A	109.2
O1—Zn1—Cl1	111.15 (7)	C9—C8—H8A	109.2
N1—Zn1—Cl1	110.44 (7)	N1—C8—H8B	109.2
Cl2—Zn1—Cl1	115.64 (3)	C9—C8—H8B	109.2
C7—N1—C8	118.0 (2)	H8A—C8—H8B	107.9
C7—N1—Zn1	119.60 (19)	N2—C9—C8	111.9 (2)
C8—N1—Zn1	122.37 (19)	N2—C9—H9A	109.2
C9—N2—C10	116.2 (2)	C8—C9—H9A	109.2
C9—N2—H2A	108.2	N2—C9—H9B	109.2
C10—N2—H2A	108.2	C8—C9—H9B	109.2
C9—N2—H2B	108.2	H9A—C9—H9B	107.9
C10—N2—H2B	108.2	C12—C10—C11	113.4 (3)
H2A—N2—H2B	107.4	C12—C10—N2	112.1 (3)
C2—O1—Zn1	122.43 (17)	C11—C10—N2	109.0 (3)
C4—O2—C13	118.4 (3)	C12—C10—H10	107.3
C6—C1—C2	118.2 (3)	C11—C10—H10	107.3
C6—C1—C7	116.0 (3)	N2—C10—H10	107.3
C2—C1—C7	125.8 (3)	C10—C11—H11A	109.5
O1—C2—C3	118.5 (2)	C10—C11—H11B	109.5
O1—C2—C1	123.9 (2)	H11A—C11—H11B	109.5
C3—C2—C1	117.6 (3)	C10—C11—H11C	109.5
C4—C3—C2	122.1 (3)	H11A—C11—H11C	109.5
C4—C3—H3	118.9	H11B—C11—H11C	109.5
C2—C3—H3	118.9	C10—C12—H12A	109.5
O2—C4—C3	114.6 (3)	C10—C12—H12B	109.5
O2—C4—C5	124.6 (3)	H12A—C12—H12B	109.5
C3—C4—C5	120.8 (3)	C10—C12—H12C	109.5
C6—C5—C4	118.1 (3)	H12A—C12—H12C	109.5
C6—C5—H5	121.0	H12B—C12—H12C	109.5
C4—C5—H5	121.0	O2—C13—H13A	109.5
C5—C6—C1	123.2 (3)	O2—C13—H13B	109.5
C5—C6—H6	118.4	H13A—C13—H13B	109.5
C1—C6—H6	118.4	O2—C13—H13C	109.5
N1—C7—C1	127.6 (3)	H13A—C13—H13C	109.5
N1—C7—H7	116.2	H13B—C13—H13C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl2i	0.90	2.62	3.357 (2)	140
N2—H2B···O1i	0.90	1.91	2.782 (3)	162
N2—H2A···Cl1	0.90	2.97	3.483 (2)	118

Zn1—O1	1.9425 (19)
Zn1—N1	1.997 (2)
Zn1—Cl2	2.2290 (9)
Zn1—Cl1	2.2554 (10)

O1—Zn1—N1	97.16 (9)
O1—Zn1—Cl2	107.02 (6)
N1—Zn1—Cl2	113.82 (7)
O1—Zn1—Cl1	111.15 (7)
N1—Zn1—Cl1	110.44 (7)
Cl2—Zn1—Cl1	115.64 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl2i	0.90	2.62	3.357 (2)	140
N2—H2B⋯O1i	0.90	1.91	2.782 (3)	162
N2—H2A⋯Cl1	0.90	2.97	3.483 (2)	118

Symmetry code: (i) .