Dichlorido(2-{[3-(morpholin-4-ium-4-yl)prop-yl]imino-meth-yl}phenolate)zinc.

In the zwitterionic zinc title complex, [ZnCl(2)(C(14)H(20)N(2)O(2))], the Zn(II) ion is four-coordinated in a distorted tetra-hedral geometry. The Schiff base ligand employs its phenolate O and imine N atoms to coordinate the metal atom in a bidentate mode. Two Cl atoms complete the tetra-hedral coordination environment. In the crystal, a pair of N-H⋯O hydrogen bonds connect the mol-ecules into a centrosymmetric dimer. C-H⋯O, C-H⋯Cl and C-H⋯π inter-actions are also observed.

Related literature

For related structures of similar zwitterionic ZnCl2 complexes, see: Qiu (2006 ▶); Ye & You (2008 ▶); Zhu (2008 ▶).

Experimental

Crystal data

[ZnCl2(C14H20N2O2)]

M = 384.59

Monoclinic,

a = 8.11276 (10) Å

b = 11.21021 (13) Å

c = 18.4097 (2) Å

β = 92.0168 (6)°

V = 1673.24 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.79 mm−1

T = 100 K

0.37 × 0.32 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.557, T max = 0.663

14420 measured reflections

3824 independent reflections

3557 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.051

S = 1.07

3824 reflections

193 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811022021/is2701sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022021/is2701Isup2.hkl

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

[ZnCl2(C14H20N2O2)]	F(000) = 792
Mr = 384.59	Dx = 1.527 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9373 reflections
a = 8.11276 (10) Å	θ = 2.2–30.4°
b = 11.21021 (13) Å	µ = 1.79 mm−1
c = 18.4097 (2) Å	T = 100 K
β = 92.0168 (6)°	Block, yellow
V = 1673.24 (4) Å3	0.37 × 0.32 × 0.25 mm
Z = 4

Bruker APEXII CCD diffractometer	3824 independent reflections
Radiation source: fine-focus sealed tube	3557 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.557, Tmax = 0.663	k = −14→14
14420 measured reflections	l = −23→23

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0237P)2 + 0.6991P] where P = (Fo2 + 2Fc2)/3
3824 reflections	(Δ/σ)max = 0.003
193 parameters	Δρmax = 0.34 e Å−3
1 restraint	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
Zn1	0.187917 (17)	0.093296 (13)	1.107214 (8)	0.01475 (5)
Cl1	0.22466 (4)	−0.09919 (3)	1.084342 (19)	0.02075 (8)
Cl2	0.33968 (4)	0.15593 (3)	1.205005 (18)	0.01907 (7)
O1	−0.04186 (11)	0.13291 (8)	1.12739 (5)	0.01608 (18)
O2	0.13093 (14)	−0.02283 (10)	0.65039 (5)	0.0276 (2)
N1	0.20412 (13)	0.20247 (10)	1.02150 (6)	0.0159 (2)
N2	0.16476 (13)	0.05293 (10)	0.79901 (6)	0.0135 (2)
H2N	0.1344 (19)	−0.0140 (12)	0.8218 (8)	0.016*
C1	−0.12380 (15)	0.22475 (11)	1.09867 (7)	0.0137 (2)
C2	−0.28113 (16)	0.25169 (12)	1.12420 (7)	0.0163 (2)
H2	−0.3253	0.2032	1.1611	0.020*
C3	−0.37327 (16)	0.34666 (12)	1.09714 (7)	0.0186 (3)
H3	−0.4787	0.3627	1.1158	0.022*
C4	−0.31222 (17)	0.41883 (12)	1.04277 (8)	0.0196 (3)
H4	−0.3743	0.4849	1.0247	0.024*
C5	−0.16034 (17)	0.39287 (12)	1.01564 (7)	0.0173 (3)
H5	−0.1203	0.4405	0.9774	0.021*
C6	−0.06264 (15)	0.29814 (11)	1.04276 (7)	0.0142 (2)
C7	0.09231 (16)	0.28065 (11)	1.00702 (7)	0.0159 (2)
H7	0.1134	0.3336	0.9682	0.019*
C8	0.34713 (16)	0.19638 (13)	0.97446 (7)	0.0194 (3)
H8A	0.4473	0.1769	1.0044	0.023*
H8B	0.3641	0.2753	0.9518	0.023*
C9	0.32253 (16)	0.10212 (12)	0.91483 (7)	0.0170 (3)
H9A	0.4296	0.0847	0.8929	0.020*
H9B	0.2812	0.0274	0.9363	0.020*
C10	0.20034 (15)	0.14566 (11)	0.85628 (7)	0.0152 (2)
H10A	0.0960	0.1682	0.8790	0.018*
H10B	0.2452	0.2178	0.8331	0.018*
C11	0.02330 (16)	0.09176 (11)	0.74944 (7)	0.0171 (3)
H11A	0.0509	0.1679	0.7255	0.020*
H11B	−0.0763	0.1045	0.7780	0.020*
C12	−0.01012 (18)	−0.00338 (13)	0.69264 (7)	0.0224 (3)
H12A	−0.0405	−0.0787	0.7168	0.027*
H12B	−0.1042	0.0214	0.6604	0.027*
C13	0.26442 (19)	−0.06439 (14)	0.69587 (8)	0.0253 (3)
H13A	0.3610	−0.0801	0.6659	0.030*
H13B	0.2328	−0.1403	0.7190	0.030*
C14	0.31118 (16)	0.02596 (12)	0.75431 (7)	0.0180 (3)
H14A	0.4018	−0.0062	0.7860	0.022*
H14B	0.3505	0.1002	0.7315	0.022*

	U11	U22	U33	U12	U13	U23
Zn1	0.01268 (8)	0.01573 (8)	0.01592 (9)	0.00041 (5)	0.00142 (6)	−0.00096 (5)
Cl1	0.01746 (15)	0.01744 (15)	0.02752 (17)	0.00001 (11)	0.00307 (13)	−0.00615 (12)
Cl2	0.01577 (14)	0.02111 (16)	0.02017 (16)	0.00145 (11)	−0.00147 (11)	−0.00506 (12)
O1	0.0137 (4)	0.0163 (4)	0.0184 (5)	0.0015 (3)	0.0024 (3)	0.0039 (4)
O2	0.0390 (6)	0.0322 (6)	0.0117 (5)	0.0108 (5)	0.0007 (4)	−0.0017 (4)
N1	0.0148 (5)	0.0191 (5)	0.0140 (5)	−0.0042 (4)	0.0023 (4)	−0.0036 (4)
N2	0.0153 (5)	0.0139 (5)	0.0114 (5)	0.0016 (4)	0.0022 (4)	0.0009 (4)
C1	0.0147 (6)	0.0137 (6)	0.0127 (6)	−0.0014 (4)	−0.0014 (4)	−0.0014 (4)
C2	0.0153 (6)	0.0170 (6)	0.0165 (6)	−0.0005 (5)	0.0010 (5)	0.0012 (5)
C3	0.0137 (6)	0.0202 (6)	0.0219 (7)	0.0011 (5)	−0.0010 (5)	−0.0014 (5)
C4	0.0192 (6)	0.0171 (6)	0.0220 (7)	0.0014 (5)	−0.0066 (5)	0.0019 (5)
C5	0.0219 (6)	0.0165 (6)	0.0134 (6)	−0.0039 (5)	−0.0035 (5)	0.0008 (5)
C6	0.0164 (6)	0.0139 (6)	0.0121 (6)	−0.0019 (4)	−0.0007 (5)	−0.0016 (4)
C7	0.0205 (6)	0.0157 (6)	0.0117 (6)	−0.0056 (5)	0.0011 (5)	−0.0013 (5)
C8	0.0141 (6)	0.0269 (7)	0.0173 (6)	−0.0057 (5)	0.0035 (5)	−0.0040 (5)
C9	0.0135 (6)	0.0222 (7)	0.0154 (6)	0.0004 (5)	0.0008 (5)	−0.0025 (5)
C10	0.0165 (6)	0.0150 (6)	0.0142 (6)	0.0001 (5)	0.0018 (5)	−0.0019 (5)
C11	0.0183 (6)	0.0189 (6)	0.0138 (6)	0.0042 (5)	−0.0017 (5)	0.0014 (5)
C12	0.0284 (7)	0.0240 (7)	0.0143 (6)	0.0020 (6)	−0.0042 (5)	0.0000 (5)
C13	0.0333 (8)	0.0257 (7)	0.0169 (7)	0.0105 (6)	0.0037 (6)	−0.0020 (5)
C14	0.0199 (6)	0.0194 (6)	0.0153 (6)	0.0055 (5)	0.0065 (5)	0.0020 (5)

Zn1—O1	1.9644 (9)	C5—H5	0.9500
Zn1—N1	2.0049 (11)	C6—C7	1.4526 (18)
Zn1—Cl1	2.2206 (3)	C7—H7	0.9500
Zn1—Cl2	2.2570 (3)	C8—C9	1.5318 (18)
O1—C1	1.3254 (15)	C8—H8A	0.9900
O2—C12	1.4230 (17)	C8—H8B	0.9900
O2—C13	1.4238 (18)	C9—C10	1.5190 (18)
N1—C7	1.2825 (17)	C9—H9A	0.9900
N1—C8	1.4736 (16)	C9—H9B	0.9900
N2—C14	1.4995 (16)	C10—H10A	0.9900
N2—C10	1.5012 (16)	C10—H10B	0.9900
N2—C11	1.5052 (16)	C11—C12	1.5114 (18)
N2—H2N	0.898 (13)	C11—H11A	0.9900
C1—C2	1.4084 (17)	C11—H11B	0.9900
C1—C6	1.4206 (17)	C12—H12A	0.9900
C2—C3	1.3836 (18)	C12—H12B	0.9900
C2—H2	0.9500	C13—C14	1.516 (2)
C3—C4	1.392 (2)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C4—C5	1.377 (2)	C14—H14A	0.9900
C4—H4	0.9500	C14—H14B	0.9900
C5—C6	1.4062 (18)
O1—Zn1—N1	95.72 (4)	C9—C8—H8A	109.3
O1—Zn1—Cl1	112.96 (3)	N1—C8—H8B	109.3
N1—Zn1—Cl1	115.53 (3)	C9—C8—H8B	109.3
O1—Zn1—Cl2	105.87 (3)	H8A—C8—H8B	108.0
N1—Zn1—Cl2	112.88 (3)	C10—C9—C8	110.63 (11)
Cl1—Zn1—Cl2	112.363 (13)	C10—C9—H9A	109.5
C1—O1—Zn1	124.48 (8)	C8—C9—H9A	109.5
C12—O2—C13	109.77 (10)	C10—C9—H9B	109.5
C7—N1—C8	118.38 (11)	C8—C9—H9B	109.5
C7—N1—Zn1	121.01 (9)	H9A—C9—H9B	108.1
C8—N1—Zn1	120.60 (9)	N2—C10—C9	112.36 (10)
C14—N2—C10	112.86 (10)	N2—C10—H10A	109.1
C14—N2—C11	109.11 (10)	C9—C10—H10A	109.1
C10—N2—C11	110.44 (10)	N2—C10—H10B	109.1
C14—N2—H2N	108.8 (10)	C9—C10—H10B	109.1
C10—N2—H2N	107.5 (10)	H10A—C10—H10B	107.9
C11—N2—H2N	108.0 (10)	N2—C11—C12	109.25 (10)
O1—C1—C2	118.76 (11)	N2—C11—H11A	109.8
O1—C1—C6	123.77 (11)	C12—C11—H11A	109.8
C2—C1—C6	117.47 (11)	N2—C11—H11B	109.8
C3—C2—C1	121.96 (12)	C12—C11—H11B	109.8
C3—C2—H2	119.0	H11A—C11—H11B	108.3
C1—C2—H2	119.0	O2—C12—C11	110.99 (12)
C2—C3—C4	120.32 (13)	O2—C12—H12A	109.4
C2—C3—H3	119.8	C11—C12—H12A	109.4
C4—C3—H3	119.8	O2—C12—H12B	109.4
C5—C4—C3	118.93 (12)	C11—C12—H12B	109.4
C5—C4—H4	120.5	H12A—C12—H12B	108.0
C3—C4—H4	120.5	O2—C13—C14	111.40 (11)
C4—C5—C6	122.09 (12)	O2—C13—H13A	109.3
C4—C5—H5	119.0	C14—C13—H13A	109.3
C6—C5—H5	119.0	O2—C13—H13B	109.3
C5—C6—C1	119.19 (12)	C14—C13—H13B	109.3
C5—C6—C7	115.28 (12)	H13A—C13—H13B	108.0
C1—C6—C7	125.44 (12)	N2—C14—C13	109.93 (11)
N1—C7—C6	127.96 (12)	N2—C14—H14A	109.7
N1—C7—H7	116.0	C13—C14—H14A	109.7
C6—C7—H7	116.0	N2—C14—H14B	109.7
N1—C8—C9	111.57 (10)	C13—C14—H14B	109.7
N1—C8—H8A	109.3	H14A—C14—H14B	108.2

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1i	0.90 (1)	1.81 (1)	2.6954 (14)	170.(2)
C5—H5···O2ii	0.95	2.39	3.2161 (16)	146
C9—H9A···Cl1iii	0.99	2.83	3.6732 (13)	144
C10—H10A···Cl1i	0.99	2.82	3.6905 (13)	147
C14—H14A···Cl2iii	0.99	2.69	3.5486 (13)	146
C14—H14B···Cl2iv	0.99	2.78	3.6890 (14)	153
C12—H12B···Cg1v	0.99	2.57	3.43663 (15)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1i	0.90 (1)	1.81 (1)	2.6954 (14)	170 (2)
C5—H5⋯O2ii	0.95	2.39	3.2161 (16)	146
C9—H9A⋯Cl1iii	0.99	2.83	3.6732 (13)	144
C10—H10A⋯Cl1i	0.99	2.82	3.6905 (13)	147
C14—H14A⋯Cl2iii	0.99	2.69	3.5486 (13)	146
C14—H14B⋯Cl2iv	0.99	2.78	3.6890 (14)	153
C12—H12B⋯Cg1v	0.99	2.57	3.4366 (2)	146

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .