Dichlorido(2-{[2-(piperazin-4-ium-1-yl)eth-yl]imino-meth-yl}phenolate)cadmium(II).

In the title compound, [CdCl(2)(C(13)H(19)N(3)O)], the Cd(II) ion is penta-coordinated with the N,N,O-tridentate Schiff base 2-{[2-(piperazin-4-ium-1-yl)eth-yl]imino-meth-yl}phenolate ligand and two Cl atoms in a highly distorted square-pyramidal geometry; the piperazine ring adopts a chair conformation. In the crystal structure, adjacent mol-ecules are linked together via N-H⋯O and N-H⋯Cl hydrogen bonds, forming infinite layers parallel to the ab plane. The layers are further connected through C-H⋯Cl inter-actions into a three-dimensional network.

Related literature

For related structures, see: Mukhopadhyay et al. (2003 ▶); Xu et al. (2008 ▶).

Experimental

Crystal data

[CdCl2(C13H19N3O)]

M = 416.61

Orthorhombic,

a = 14.7512 (16) Å

b = 13.1406 (15) Å

c = 16.6188 (19) Å

V = 3221.4 (6) Å3

Z = 8

Mo Kα radiation

μ = 1.69 mm−1

T = 100 K

0.45 × 0.39 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.518, T max = 0.751

38841 measured reflections

3700 independent reflections

3409 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.045

S = 1.06

3700 reflections

187 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (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 datablocks I, global. DOI: 10.1107/S1600536810032563/pv2318sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032563/pv2318Isup2.hkl

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

[CdCl2(C13H19N3O)]	F(000) = 1664
Mr = 416.61	Dx = 1.718 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9877 reflections
a = 14.7512 (16) Å	θ = 2.4–31.3°
b = 13.1406 (15) Å	µ = 1.69 mm−1
c = 16.6188 (19) Å	T = 100 K
V = 3221.4 (6) Å3	Block, yellow
Z = 8	0.45 × 0.39 × 0.18 mm

Bruker APEXII CCD diffractometer	3700 independent reflections
Radiation source: fine-focus sealed tube	3409 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.518, Tmax = 0.751	k = −17→17
38841 measured reflections	l = −21→21

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)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.045	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0187P)2 + 2.1332P] where P = (Fo2 + 2Fc2)/3
3700 reflections	(Δ/σ)max = 0.002
187 parameters	Δρmax = 0.44 e Å−3
2 restraints	Δρmin = −0.28 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
Cd1	0.915609 (7)	0.521115 (8)	0.335271 (6)	0.01335 (4)
Cl1	0.80478 (3)	0.46142 (3)	0.23256 (2)	0.02000 (8)
Cl2	1.05575 (2)	0.57074 (3)	0.26583 (2)	0.01803 (8)
O1	0.98159 (7)	0.37354 (9)	0.37625 (7)	0.0192 (2)
N1	0.87369 (9)	0.52146 (10)	0.46665 (8)	0.0162 (3)
N2	0.83315 (8)	0.68754 (10)	0.35360 (8)	0.0139 (2)
N3	0.88695 (9)	0.83051 (10)	0.22922 (8)	0.0149 (2)
H3A	0.8533 (12)	0.8859 (13)	0.2359 (11)	0.022*
H3B	0.9244 (12)	0.8437 (16)	0.1887 (11)	0.022*
C1	0.95272 (10)	0.31114 (12)	0.43163 (9)	0.0169 (3)
C2	0.96780 (11)	0.20498 (12)	0.42363 (10)	0.0195 (3)
H2	0.9967	0.1802	0.3765	0.023*
C3	0.94174 (11)	0.13662 (13)	0.48221 (10)	0.0220 (3)
H3	0.9523	0.0660	0.4742	0.026*
C4	0.90004 (11)	0.16929 (13)	0.55317 (10)	0.0213 (3)
H4	0.8837	0.1221	0.5940	0.026*
C5	0.88317 (10)	0.27220 (13)	0.56245 (9)	0.0194 (3)
H5	0.8550	0.2953	0.6105	0.023*
C6	0.90643 (10)	0.34411 (12)	0.50271 (9)	0.0167 (3)
C7	0.87494 (10)	0.44702 (13)	0.51703 (9)	0.0172 (3)
H7	0.8527	0.4611	0.5695	0.021*
C8	0.83000 (10)	0.61616 (12)	0.49269 (9)	0.0178 (3)
H8A	0.8766	0.6657	0.5100	0.021*
H8B	0.7895	0.6024	0.5389	0.021*
C9	0.77532 (10)	0.66006 (12)	0.42318 (9)	0.0172 (3)
H9A	0.7296	0.6095	0.4058	0.021*
H9B	0.7426	0.7214	0.4419	0.021*
C10	0.88602 (10)	0.77994 (12)	0.37278 (9)	0.0164 (3)
H10A	0.9254	0.7662	0.4198	0.020*
H10B	0.8440	0.8357	0.3874	0.020*
C11	0.94408 (10)	0.81319 (12)	0.30220 (9)	0.0158 (3)
H11A	0.9765	0.8768	0.3162	0.019*
H11B	0.9899	0.7602	0.2906	0.019*
C12	0.82875 (10)	0.74064 (12)	0.21146 (9)	0.0166 (3)
H12A	0.8674	0.6825	0.1954	0.020*
H12B	0.7878	0.7567	0.1660	0.020*
C13	0.77292 (10)	0.71146 (12)	0.28467 (9)	0.0158 (3)
H13A	0.7321	0.7684	0.2992	0.019*
H13B	0.7350	0.6514	0.2719	0.019*

	U11	U22	U33	U12	U13	U23
Cd1	0.01279 (7)	0.01314 (7)	0.01412 (7)	0.00111 (4)	0.00214 (4)	0.00129 (4)
Cl1	0.01838 (18)	0.01817 (18)	0.02346 (19)	−0.00298 (14)	−0.00124 (14)	−0.00369 (14)
Cl2	0.01453 (16)	0.01461 (17)	0.02495 (19)	−0.00003 (13)	0.00517 (14)	0.00176 (14)
O1	0.0201 (5)	0.0189 (5)	0.0186 (5)	0.0057 (4)	0.0045 (4)	0.0040 (4)
N1	0.0132 (6)	0.0189 (7)	0.0164 (6)	0.0015 (5)	0.0010 (5)	−0.0002 (5)
N2	0.0117 (6)	0.0146 (6)	0.0153 (6)	−0.0007 (5)	0.0005 (5)	0.0009 (5)
N3	0.0153 (6)	0.0127 (6)	0.0166 (6)	−0.0006 (5)	0.0005 (5)	0.0007 (5)
C1	0.0134 (7)	0.0180 (7)	0.0192 (7)	0.0003 (6)	−0.0030 (6)	0.0024 (6)
C2	0.0174 (7)	0.0190 (8)	0.0222 (8)	0.0013 (6)	−0.0020 (6)	0.0017 (6)
C3	0.0178 (7)	0.0175 (8)	0.0306 (9)	−0.0017 (6)	−0.0083 (6)	0.0054 (7)
C4	0.0167 (7)	0.0244 (8)	0.0229 (8)	−0.0052 (6)	−0.0065 (6)	0.0098 (7)
C5	0.0147 (7)	0.0273 (8)	0.0161 (7)	−0.0045 (6)	−0.0034 (6)	0.0050 (6)
C6	0.0143 (7)	0.0198 (8)	0.0158 (7)	−0.0019 (6)	−0.0024 (6)	0.0034 (6)
C7	0.0128 (7)	0.0241 (8)	0.0147 (7)	−0.0013 (6)	0.0000 (5)	0.0003 (6)
C8	0.0183 (7)	0.0195 (7)	0.0156 (7)	0.0017 (6)	0.0035 (6)	−0.0006 (6)
C9	0.0139 (7)	0.0179 (7)	0.0198 (7)	0.0011 (6)	0.0040 (6)	0.0009 (6)
C10	0.0153 (7)	0.0168 (7)	0.0172 (7)	−0.0021 (6)	0.0004 (6)	−0.0023 (6)
C11	0.0139 (7)	0.0155 (7)	0.0179 (7)	−0.0019 (6)	−0.0009 (6)	0.0003 (6)
C12	0.0164 (7)	0.0157 (7)	0.0177 (7)	−0.0023 (6)	−0.0025 (6)	−0.0004 (6)
C13	0.0124 (7)	0.0157 (7)	0.0192 (7)	−0.0007 (5)	−0.0020 (6)	0.0009 (6)

Cd1—N1	2.2693 (13)	C4—C5	1.384 (2)
Cd1—O1	2.2740 (11)	C4—H4	0.9500
Cd1—Cl2	2.4557 (4)	C5—C6	1.413 (2)
Cd1—Cl1	2.4904 (4)	C5—H5	0.9500
Cd1—N2	2.5209 (13)	C6—C7	1.450 (2)
O1—C1	1.3042 (19)	C7—H7	0.9500
N1—C7	1.288 (2)	C8—C9	1.522 (2)
N1—C8	1.4667 (19)	C8—H8A	0.9900
N2—C10	1.4779 (19)	C8—H8B	0.9900
N2—C9	1.4816 (19)	C9—H9A	0.9900
N2—C13	1.4833 (19)	C9—H9B	0.9900
N3—C12	1.4897 (19)	C10—C11	1.517 (2)
N3—C11	1.4943 (19)	C10—H10A	0.9900
N3—H3A	0.889 (15)	C10—H10B	0.9900
N3—H3B	0.887 (15)	C11—H11A	0.9900
C1—C2	1.419 (2)	C11—H11B	0.9900
C1—C6	1.432 (2)	C12—C13	1.518 (2)
C2—C3	1.379 (2)	C12—H12A	0.9900
C2—H2	0.9500	C12—H12B	0.9900
C3—C4	1.398 (3)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
N1—Cd1—O1	80.22 (4)	C5—C6—C7	115.51 (14)
N1—Cd1—Cl2	132.92 (3)	C1—C6—C7	124.80 (14)
O1—Cd1—Cl2	90.39 (3)	N1—C7—C6	127.33 (14)
N1—Cd1—Cl1	118.77 (3)	N1—C7—H7	116.3
O1—Cd1—Cl1	102.57 (3)	C6—C7—H7	116.3
Cl2—Cd1—Cl1	108.309 (15)	N1—C8—C9	109.30 (12)
N1—Cd1—N2	75.55 (4)	N1—C8—H8A	109.8
O1—Cd1—N2	155.52 (4)	C9—C8—H8A	109.8
Cl2—Cd1—N2	103.45 (3)	N1—C8—H8B	109.8
Cl1—Cd1—N2	92.25 (3)	C9—C8—H8B	109.8
C1—O1—Cd1	127.43 (9)	H8A—C8—H8B	108.3
C7—N1—C8	117.32 (13)	N2—C9—C8	112.31 (12)
C7—N1—Cd1	128.33 (11)	N2—C9—H9A	109.1
C8—N1—Cd1	113.90 (9)	C8—C9—H9A	109.1
C10—N2—C9	109.61 (12)	N2—C9—H9B	109.1
C10—N2—C13	107.97 (12)	C8—C9—H9B	109.1
C9—N2—C13	108.04 (11)	H9A—C9—H9B	107.9
C10—N2—Cd1	118.96 (9)	N2—C10—C11	111.59 (12)
C9—N2—Cd1	99.25 (9)	N2—C10—H10A	109.3
C13—N2—Cd1	112.30 (9)	C11—C10—H10A	109.3
C12—N3—C11	111.41 (12)	N2—C10—H10B	109.3
C12—N3—H3A	110.6 (13)	C11—C10—H10B	109.3
C11—N3—H3A	109.8 (12)	H10A—C10—H10B	108.0
C12—N3—H3B	111.3 (14)	N3—C11—C10	110.68 (12)
C11—N3—H3B	107.1 (13)	N3—C11—H11A	109.5
H3A—N3—H3B	106.4 (19)	C10—C11—H11A	109.5
O1—C1—C2	120.06 (14)	N3—C11—H11B	109.5
O1—C1—C6	123.22 (14)	C10—C11—H11B	109.5
C2—C1—C6	116.72 (14)	H11A—C11—H11B	108.1
C3—C2—C1	122.04 (16)	N3—C12—C13	110.73 (12)
C3—C2—H2	119.0	N3—C12—H12A	109.5
C1—C2—H2	119.0	C13—C12—H12A	109.5
C2—C3—C4	121.21 (16)	N3—C12—H12B	109.5
C2—C3—H3	119.4	C13—C12—H12B	109.5
C4—C3—H3	119.4	H12A—C12—H12B	108.1
C5—C4—C3	118.25 (15)	N2—C13—C12	110.34 (12)
C5—C4—H4	120.9	N2—C13—H13A	109.6
C3—C4—H4	120.9	C12—C13—H13A	109.6
C4—C5—C6	122.12 (15)	N2—C13—H13B	109.6
C4—C5—H5	118.9	C12—C13—H13B	109.6
C6—C5—H5	118.9	H13A—C13—H13B	108.1
C5—C6—C1	119.56 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl1i	0.89 (2)	2.53 (2)	3.3108 (14)	146.(2)
N3—H3A···Cl2ii	0.89 (2)	2.78 (2)	3.2689 (14)	116.(2)
N3—H3B···O1ii	0.89 (2)	1.80 (2)	2.6743 (17)	167.(2)
C11—H11B···Cl2	0.99	2.70	3.6372 (16)	157.
C13—H13B···Cl1	0.99	2.78	3.4302 (16)	124.
C4—H4···Cl1iii	0.95	2.80	3.7165 (17)	161.
C13—H13A···Cl1i	0.99	2.82	3.5851 (16)	134.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯Cl1i	0.89 (2)	2.53 (2)	3.3108 (14)	146 (2)
N3—H3A⋯Cl2ii	0.89 (2)	2.78 (2)	3.2689 (14)	116 (2)
N3—H3B⋯O1ii	0.89 (2)	1.80 (2)	2.6743 (17)	167 (2)
C11—H11B⋯Cl2	0.99	2.70	3.6372 (16)	157
C13—H13B⋯Cl1	0.99	2.78	3.4302 (16)	124
C4—H4⋯Cl1iii	0.95	2.80	3.7165 (17)	161
C13—H13A⋯Cl1i	0.99	2.82	3.5851 (16)	134

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