Dichlorido{2-[2-(dimethyl-ammonio)ethyl-imino-meth-yl]-6-methoxy-phenolato}zinc(II).

The structure of the title complex, [ZnCl(2)(C(12)H(18)N(2)O(2))], contains a zwitterionic Schiff base ligand. The complex adopts a distorted tetra-hedral coordination geometry around the metal centre with the Schiff base ligand coordinated in a bidentate fashion via the imine N and phenolate O atoms. In the crystal, inter-molecular N-H⋯O and C-H⋯Cl hydrogen bonds link the mol-ecules into chains parallel to the c-glide planes.

Related literature

For bidentate Schiff base–Zn(II) complexes, see: Qiu (2006 ▶); Wang & Qiu (2006 ▶); Ye & You (2008 ▶); You (2005a ▶,b ▶); Zhu (2008 ▶).

Experimental

Crystal data

[ZnCl2(C12H18N2O2)]

M = 358.55

Monoclinic,

a = 8.5621 (6) Å

b = 16.9642 (12) Å

c = 13.1106 (7) Å

β = 127.732 (3)°

V = 1506.08 (17) Å3

Z = 4

Mo Kα radiation

μ = 1.98 mm−1

T = 298 K

0.32 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.552, T max = 0.649

8355 measured reflections

2960 independent reflections

2439 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.075

S = 1.01

2960 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028220/bh2237sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028220/bh2237Isup2.hkl

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

[ZnCl2(C12H18N2O2)]	F(000) = 736
Mr = 358.55	Dx = 1.581 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4320 reflections
a = 8.5621 (6) Å	θ = 2.4–26.0°
b = 16.9642 (12) Å	µ = 1.98 mm−1
c = 13.1106 (7) Å	T = 298 K
β = 127.732 (3)°	Block, brown
V = 1506.08 (17) Å3	0.32 × 0.25 × 0.22 mm
Z = 4

Bruker SMART APEXII diffractometer	2960 independent reflections
Radiation source: fine-focus sealed tube	2439 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→9
Tmin = 0.552, Tmax = 0.649	k = −20→20
8355 measured reflections	l = −10→16

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0461P)2] where P = (Fo2 + 2Fc2)/3
2960 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.34 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Zn1	0.68123 (3)	0.747503 (13)	0.52685 (2)	0.02988 (10)
Cl1	0.60094 (9)	0.72171 (4)	0.65804 (6)	0.04492 (16)
Cl2	0.86631 (8)	0.65127 (4)	0.53283 (6)	0.04647 (17)
O1	0.7870 (2)	0.85437 (8)	0.55417 (13)	0.0336 (3)
O2	0.9469 (2)	0.99419 (9)	0.62283 (15)	0.0432 (4)
N1	0.1190 (3)	0.63462 (11)	0.31873 (17)	0.0357 (4)
H1	0.0110	0.6259	0.2358	0.043*
N2	0.4369 (2)	0.76199 (10)	0.34509 (17)	0.0285 (4)
C1	0.1242 (4)	0.57202 (15)	0.4010 (2)	0.0512 (6)
H1A	0.0034	0.5732	0.3910	0.077*
H1B	0.2336	0.5813	0.4897	0.077*
H1C	0.1388	0.5214	0.3751	0.077*
C2	0.0953 (3)	0.71360 (15)	0.3580 (2)	0.0442 (6)
H2A	0.0800	0.7530	0.2999	0.066*
H2B	0.2101	0.7253	0.4441	0.066*
H2C	−0.0194	0.7133	0.3552	0.066*
C3	0.2983 (3)	0.62794 (13)	0.3237 (2)	0.0364 (5)
H3A	0.2912	0.5786	0.2837	0.044*
H3B	0.4144	0.6258	0.4134	0.044*
C4	0.3242 (3)	0.69479 (13)	0.2580 (2)	0.0354 (5)
H4A	0.3921	0.6749	0.2253	0.043*
H4B	0.1951	0.7132	0.1850	0.043*
C5	0.3886 (3)	0.83097 (13)	0.2944 (2)	0.0324 (5)
H5	0.2768	0.8338	0.2087	0.039*
C6	0.4879 (3)	0.90494 (12)	0.35490 (19)	0.0302 (5)
C7	0.3821 (3)	0.97261 (14)	0.2809 (2)	0.0393 (5)
H7	0.2582	0.9666	0.2018	0.047*
C8	0.4579 (4)	1.04639 (14)	0.3232 (2)	0.0432 (6)
H8	0.3841	1.0903	0.2750	0.052*
C9	0.6463 (3)	1.05555 (13)	0.4387 (2)	0.0397 (5)
H9	0.6988	1.1059	0.4674	0.048*
C10	0.7563 (3)	0.99069 (12)	0.5115 (2)	0.0321 (5)
C11	0.6771 (3)	0.91289 (12)	0.47493 (19)	0.0280 (4)
C12	1.0452 (4)	1.06907 (14)	0.6573 (3)	0.0537 (7)
H12A	0.9871	1.1044	0.6828	0.081*
H12B	1.0314	1.0907	0.5845	0.081*
H12C	1.1827	1.0622	0.7276	0.081*

	U11	U22	U33	U12	U13	U23
Zn1	0.02911 (15)	0.02351 (15)	0.03349 (16)	−0.00104 (9)	0.01735 (12)	0.00050 (9)
Cl1	0.0429 (3)	0.0566 (4)	0.0423 (3)	0.0001 (3)	0.0297 (3)	0.0034 (3)
Cl2	0.0428 (3)	0.0418 (3)	0.0553 (4)	0.0101 (3)	0.0303 (3)	−0.0005 (3)
O1	0.0304 (7)	0.0224 (8)	0.0340 (8)	−0.0004 (6)	0.0126 (6)	0.0016 (6)
O2	0.0423 (9)	0.0256 (8)	0.0426 (9)	−0.0090 (7)	0.0163 (8)	−0.0024 (7)
N1	0.0308 (9)	0.0373 (11)	0.0342 (10)	−0.0060 (8)	0.0175 (8)	−0.0036 (8)
N2	0.0267 (8)	0.0282 (10)	0.0314 (9)	−0.0047 (7)	0.0183 (8)	−0.0039 (7)
C1	0.0598 (16)	0.0482 (16)	0.0506 (15)	−0.0093 (12)	0.0363 (14)	0.0020 (12)
C2	0.0353 (12)	0.0465 (15)	0.0497 (14)	0.0028 (11)	0.0254 (11)	−0.0053 (11)
C3	0.0323 (11)	0.0282 (12)	0.0454 (13)	−0.0019 (9)	0.0220 (10)	−0.0063 (9)
C4	0.0360 (11)	0.0366 (13)	0.0353 (12)	−0.0084 (9)	0.0227 (10)	−0.0113 (9)
C5	0.0286 (10)	0.0379 (13)	0.0312 (11)	0.0001 (9)	0.0186 (9)	0.0028 (9)
C6	0.0325 (10)	0.0273 (11)	0.0343 (11)	0.0011 (8)	0.0222 (9)	0.0028 (8)
C7	0.0364 (12)	0.0376 (13)	0.0380 (12)	0.0038 (10)	0.0197 (10)	0.0080 (10)
C8	0.0462 (14)	0.0292 (13)	0.0490 (14)	0.0094 (10)	0.0264 (12)	0.0145 (10)
C9	0.0508 (14)	0.0250 (12)	0.0480 (14)	−0.0013 (10)	0.0326 (12)	0.0041 (10)
C10	0.0364 (12)	0.0264 (11)	0.0334 (11)	−0.0013 (9)	0.0214 (10)	0.0004 (9)
C11	0.0317 (10)	0.0260 (11)	0.0315 (11)	0.0007 (8)	0.0219 (9)	0.0027 (8)
C12	0.0561 (16)	0.0275 (14)	0.0609 (17)	−0.0159 (11)	0.0272 (14)	−0.0082 (11)

Zn1—O1	1.9590 (14)	C3—C4	1.521 (3)
Zn1—N2	2.0034 (18)	C3—H3A	0.9700
Zn1—Cl2	2.2429 (6)	C3—H3B	0.9700
Zn1—Cl1	2.2516 (6)	C4—H4A	0.9700
O1—C11	1.324 (2)	C4—H4B	0.9700
O2—C10	1.372 (3)	C5—C6	1.450 (3)
O2—C12	1.435 (3)	C5—H5	0.9300
N1—C2	1.493 (3)	C6—C11	1.414 (3)
N1—C1	1.495 (3)	C6—C7	1.415 (3)
N1—C3	1.500 (3)	C7—C8	1.362 (3)
N1—H1	0.9100	C7—H7	0.9300
N2—C5	1.283 (3)	C8—C9	1.389 (3)
N2—C4	1.479 (3)	C8—H8	0.9300
C1—H1A	0.9600	C9—C10	1.381 (3)
C1—H1B	0.9600	C9—H9	0.9300
C1—H1C	0.9600	C10—C11	1.426 (3)
C2—H2A	0.9600	C12—H12A	0.9600
C2—H2B	0.9600	C12—H12B	0.9600
C2—H2C	0.9600	C12—H12C	0.9600
O1—Zn1—N2	97.67 (6)	H3A—C3—H3B	107.5
O1—Zn1—Cl2	115.44 (5)	N2—C4—C3	112.94 (18)
N2—Zn1—Cl2	109.39 (5)	N2—C4—H4A	109.0
O1—Zn1—Cl1	111.30 (5)	C3—C4—H4A	109.0
N2—Zn1—Cl1	110.35 (5)	N2—C4—H4B	109.0
Cl2—Zn1—Cl1	111.80 (3)	C3—C4—H4B	109.0
C11—O1—Zn1	121.55 (13)	H4A—C4—H4B	107.8
C10—O2—C12	117.37 (18)	N2—C5—C6	127.7 (2)
C2—N1—C1	109.82 (19)	N2—C5—H5	116.2
C2—N1—C3	113.83 (16)	C6—C5—H5	116.2
C1—N1—C3	109.71 (18)	C11—C6—C7	120.1 (2)
C2—N1—H1	107.8	C11—C6—C5	125.47 (19)
C1—N1—H1	107.8	C7—C6—C5	114.34 (19)
C3—N1—H1	107.8	C8—C7—C6	121.4 (2)
C5—N2—C4	116.87 (19)	C8—C7—H7	119.3
C5—N2—Zn1	119.94 (14)	C6—C7—H7	119.3
C4—N2—Zn1	122.48 (14)	C7—C8—C9	119.5 (2)
N1—C1—H1A	109.5	C7—C8—H8	120.2
N1—C1—H1B	109.5	C9—C8—H8	120.2
H1A—C1—H1B	109.5	C10—C9—C8	120.7 (2)
N1—C1—H1C	109.5	C10—C9—H9	119.7
H1A—C1—H1C	109.5	C8—C9—H9	119.7
H1B—C1—H1C	109.5	O2—C10—C9	124.4 (2)
N1—C2—H2A	109.5	O2—C10—C11	114.14 (18)
N1—C2—H2B	109.5	C9—C10—C11	121.5 (2)
H2A—C2—H2B	109.5	O1—C11—C6	125.57 (19)
N1—C2—H2C	109.5	O1—C11—C10	117.83 (18)
H2A—C2—H2C	109.5	C6—C11—C10	116.59 (18)
H2B—C2—H2C	109.5	O2—C12—H12A	109.5
N1—C3—C4	114.78 (18)	O2—C12—H12B	109.5
N1—C3—H3A	108.6	H12A—C12—H12B	109.5
C4—C3—H3A	108.6	O2—C12—H12C	109.5
N1—C3—H3B	108.6	H12A—C12—H12C	109.5
C4—C3—H3B	108.6	H12B—C12—H12C	109.5
N2—Zn1—O1—C11	14.33 (16)	C11—C6—C7—C8	−0.5 (3)
Cl2—Zn1—O1—C11	130.12 (14)	C5—C6—C7—C8	−178.3 (2)
Cl1—Zn1—O1—C11	−101.07 (15)	C6—C7—C8—C9	2.7 (4)
O1—Zn1—N2—C5	−8.41 (17)	C7—C8—C9—C10	−0.6 (4)
Cl2—Zn1—N2—C5	−128.86 (16)	C12—O2—C10—C9	−7.6 (3)
Cl1—Zn1—N2—C5	107.74 (16)	C12—O2—C10—C11	172.5 (2)
O1—Zn1—N2—C4	161.59 (15)	C8—C9—C10—O2	176.4 (2)
Cl2—Zn1—N2—C4	41.14 (16)	C8—C9—C10—C11	−3.7 (3)
Cl1—Zn1—N2—C4	−82.26 (15)	Zn1—O1—C11—C6	−9.9 (3)
C2—N1—C3—C4	−48.9 (2)	Zn1—O1—C11—C10	171.41 (14)
C1—N1—C3—C4	−172.44 (19)	C7—C6—C11—O1	177.8 (2)
C5—N2—C4—C3	−146.55 (19)	C5—C6—C11—O1	−4.7 (3)
Zn1—N2—C4—C3	43.2 (2)	C7—C6—C11—C10	−3.5 (3)
N1—C3—C4—N2	88.5 (2)	C5—C6—C11—C10	174.0 (2)
C4—N2—C5—C6	−173.07 (19)	O2—C10—C11—O1	4.4 (3)
Zn1—N2—C5—C6	−2.5 (3)	C9—C10—C11—O1	−175.5 (2)
N2—C5—C6—C11	12.0 (4)	O2—C10—C11—C6	−174.43 (18)
N2—C5—C6—C7	−170.4 (2)	C9—C10—C11—C6	5.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.91	1.97	2.842 (2)	161
N1—H1···O2i	0.91	2.38	2.985 (2)	124
C5—H5···Cl2i	0.93	2.80	3.617 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.91	1.97	2.842 (2)	161
N1—H1⋯O2i	0.91	2.38	2.985 (2)	124
C5—H5⋯Cl2i	0.93	2.80	3.617 (2)	148

Symmetry code: (i) .