Dichlorido(4-meth-oxy-2-{[2-(piperazin-4-ium-1-yl)eth-yl]imino-meth-yl}phenol-ate)cadmium.

In the title compound, [CdCl(2)(C(14)H(21)N(3)O(2))], the Schiff base ligand chelates the Cd(II) ion in an N,N,O-tridentate fashion. Two Cl atoms complete a distorted square-pyramidal coordination environment around the metal atom. In the crystal, adjacent mol-ecules are linked through C-H⋯π inter-actions into infinite chains along the a axis. The mol-ecules are further connected into a three-dimensional network via N-H⋯O, N-H⋯Cl and C-H⋯Cl inter-actions. The ethyl-ene group is disordered over two sets of sites in a 0.520 (10):0.480 (10) ratio.

Related literature

For similar structures, see: Mukhopadhyay et al. (2003 ▶); Xu et al. (2008 ▶); Saleh Salga et al. (2010 ▶). For a description of the geometry of complexes with five-coordinated metal ions, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[CdCl2(C14H21N3O2)]

M = 446.64

Monoclinic,

a = 10.1173 (9) Å

b = 16.2686 (15) Å

c = 10.3486 (10) Å

β = 103.069 (1)°

V = 1659.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.65 mm−1

T = 100 K

0.25 × 0.18 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.684, T max = 0.937

14540 measured reflections

3624 independent reflections

3138 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.061

S = 1.07

3624 reflections

225 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.65 e Å−3

Δρmin = −0.78 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 datablock(s) I, global. DOI: 10.1107/S1600536811022100/xu5230sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022100/xu5230Isup2.hkl

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

[CdCl2(C14H21N3O2)]	F(000) = 896
Mr = 446.64	Dx = 1.788 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4675 reflections
a = 10.1173 (9) Å	θ = 2.4–30.3°
b = 16.2686 (15) Å	µ = 1.65 mm−1
c = 10.3486 (10) Å	T = 100 K
β = 103.069 (1)°	Plate, yellow
V = 1659.2 (3) Å3	0.25 × 0.18 × 0.04 mm
Z = 4

Bruker APEXII CCD diffractometer	3624 independent reflections
Radiation source: fine-focus sealed tube	3138 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.684, Tmax = 0.937	k = −20→20
14540 measured reflections	l = −12→13

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0115P)2 + 3.0473P] where P = (Fo2 + 2Fc2)/3
3624 reflections	(Δ/σ)max < 0.001
225 parameters	Δρmax = 0.65 e Å−3
5 restraints	Δρmin = −0.78 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	Occ. (<1)
Cd1	0.34107 (2)	−0.052048 (13)	0.68131 (2)	0.01663 (7)
Cl1	0.56656 (8)	−0.11579 (5)	0.74780 (10)	0.0354 (2)
Cl2	0.23070 (8)	−0.07175 (5)	0.87000 (8)	0.02395 (17)
O1	0.2602 (2)	−0.15436 (13)	0.5407 (2)	0.0251 (5)
O2	−0.1051 (2)	−0.17553 (14)	0.0579 (2)	0.0268 (5)
N1	0.2318 (3)	0.02551 (17)	0.5110 (3)	0.0360 (8)
N2	0.4238 (3)	0.08960 (15)	0.7371 (3)	0.0201 (6)
N3	0.6073 (3)	0.20036 (17)	0.9144 (3)	0.0282 (7)
H3A	0.644 (3)	0.2509 (14)	0.941 (4)	0.034*
H3B	0.647 (3)	0.1620 (18)	0.972 (3)	0.034*
C1	0.1647 (3)	−0.15272 (19)	0.4325 (3)	0.0213 (7)
C2	0.1038 (3)	−0.22708 (19)	0.3799 (4)	0.0250 (7)
H2	0.1240	−0.2756	0.4316	0.030*
C3	0.0166 (3)	−0.2327 (2)	0.2574 (4)	0.0259 (7)
H3	−0.0201	−0.2846	0.2257	0.031*
C4	−0.0181 (3)	−0.16303 (19)	0.1797 (3)	0.0199 (6)
C5	0.0301 (3)	−0.08803 (19)	0.2301 (3)	0.0221 (7)
H5	0.0028	−0.0398	0.1792	0.027*
C6	0.1199 (3)	−0.08094 (18)	0.3567 (3)	0.0198 (6)
C7	0.1562 (4)	0.0024 (2)	0.3998 (4)	0.0336 (9)
H7	0.1201	0.0448	0.3390	0.040*
C8	−0.1108 (3)	−0.1114 (2)	−0.0365 (3)	0.0277 (7)
H8A	−0.1539	−0.0629	−0.0077	0.042*
H8B	−0.1639	−0.1297	−0.1230	0.042*
H8C	−0.0186	−0.0974	−0.0440	0.042*
C9	0.2794 (9)	0.1146 (3)	0.5179 (6)	0.027 (2)	0.520 (10)
H9A	0.3623	0.1195	0.4828	0.033*	0.520 (10)
H9B	0.2081	0.1500	0.4639	0.033*	0.520 (10)
C10	0.3083 (6)	0.1410 (3)	0.6602 (6)	0.0207 (17)	0.520 (10)
H10A	0.2267	0.1333	0.6965	0.025*	0.520 (10)
H10B	0.3334	0.1999	0.6674	0.025*	0.520 (10)
C9'	0.2199 (7)	0.1130 (4)	0.5540 (8)	0.0213 (18)	0.480 (10)
H9C	0.1786	0.1483	0.4775	0.026*	0.480 (10)
H9D	0.1646	0.1166	0.6215	0.026*	0.480 (10)
C10'	0.3645 (7)	0.1373 (4)	0.6114 (7)	0.0227 (19)	0.480 (10)
H10C	0.3686	0.1969	0.6314	0.027*	0.480 (10)
H10D	0.4195	0.1270	0.5452	0.027*	0.480 (10)
C11	0.5665 (4)	0.0977 (2)	0.7352 (4)	0.0374 (10)
H11A	0.5772	0.0875	0.6438	0.045*
H11B	0.6185	0.0549	0.7932	0.045*
C12	0.6273 (4)	0.1815 (2)	0.7807 (4)	0.0363 (9)
H12A	0.7255	0.1814	0.7821	0.044*
H12B	0.5833	0.2244	0.7175	0.044*
C13	0.4637 (4)	0.1933 (2)	0.9208 (4)	0.0407 (10)
H13A	0.4098	0.2365	0.8652	0.049*
H13B	0.4550	0.2012	1.0134	0.049*
C14	0.4095 (4)	0.1085 (2)	0.8714 (4)	0.0441 (11)
H14A	0.4583	0.0662	0.9329	0.053*
H14B	0.3123	0.1054	0.8735	0.053*

	U11	U22	U33	U12	U13	U23
Cd1	0.01874 (11)	0.01363 (11)	0.01584 (12)	−0.00060 (9)	0.00039 (8)	0.00174 (9)
Cl1	0.0207 (4)	0.0231 (4)	0.0576 (6)	0.0037 (3)	−0.0014 (4)	0.0042 (4)
Cl2	0.0276 (4)	0.0202 (4)	0.0259 (4)	−0.0011 (3)	0.0097 (3)	0.0048 (3)
O1	0.0382 (13)	0.0120 (10)	0.0204 (12)	0.0043 (9)	−0.0033 (10)	0.0012 (9)
O2	0.0250 (12)	0.0280 (13)	0.0245 (13)	−0.0034 (10)	−0.0007 (10)	−0.0050 (10)
N1	0.060 (2)	0.0154 (14)	0.0215 (16)	0.0037 (14)	−0.0132 (15)	−0.0005 (12)
N2	0.0188 (13)	0.0163 (12)	0.0217 (15)	−0.0021 (10)	−0.0028 (11)	0.0021 (11)
N3	0.0386 (17)	0.0143 (13)	0.0228 (17)	−0.0021 (12)	−0.0119 (13)	−0.0002 (11)
C1	0.0189 (15)	0.0175 (15)	0.0274 (18)	0.0022 (12)	0.0050 (13)	0.0013 (13)
C2	0.0249 (17)	0.0140 (15)	0.033 (2)	0.0000 (13)	0.0008 (14)	0.0041 (14)
C3	0.0233 (16)	0.0178 (15)	0.035 (2)	−0.0022 (13)	0.0036 (15)	−0.0054 (14)
C4	0.0135 (14)	0.0259 (16)	0.0187 (16)	0.0003 (12)	0.0004 (12)	−0.0044 (13)
C5	0.0251 (16)	0.0184 (15)	0.0226 (18)	0.0016 (13)	0.0049 (13)	0.0031 (13)
C6	0.0256 (16)	0.0150 (14)	0.0179 (17)	0.0009 (12)	0.0032 (13)	−0.0023 (12)
C7	0.053 (2)	0.0176 (16)	0.0223 (19)	0.0073 (16)	−0.0088 (17)	0.0040 (14)
C8	0.0235 (17)	0.0355 (19)	0.0224 (19)	0.0033 (14)	0.0015 (14)	−0.0050 (15)
C9	0.040 (5)	0.012 (3)	0.021 (4)	0.003 (3)	−0.010 (3)	−0.004 (3)
C10	0.020 (3)	0.012 (3)	0.027 (4)	−0.003 (2)	−0.002 (3)	−0.004 (3)
C9'	0.023 (4)	0.020 (4)	0.020 (4)	0.007 (3)	0.002 (3)	0.000 (3)
C10'	0.031 (4)	0.014 (3)	0.021 (4)	−0.005 (3)	0.004 (3)	0.001 (3)
C11	0.034 (2)	0.034 (2)	0.053 (3)	−0.0217 (16)	0.0285 (19)	−0.0279 (18)
C12	0.0297 (19)	0.0302 (19)	0.057 (3)	−0.0137 (15)	0.0255 (18)	−0.0224 (18)
C13	0.060 (3)	0.0272 (19)	0.046 (3)	−0.0171 (18)	0.035 (2)	−0.0180 (17)
C14	0.062 (3)	0.0273 (19)	0.058 (3)	−0.0221 (18)	0.044 (2)	−0.0194 (19)

Cd1—O1	2.241 (2)	C5—H5	0.9500
Cd1—N1	2.245 (3)	C6—C7	1.448 (4)
Cd1—N2	2.475 (2)	C7—H7	0.9500
Cd1—Cl1	2.4584 (8)	C8—H8A	0.9800
Cd1—Cl2	2.4797 (8)	C8—H8B	0.9800
O1—C1	1.303 (4)	C8—H8C	0.9800
O2—C4	1.380 (4)	C9—C10	1.498 (7)
O2—C8	1.421 (4)	C9—H9A	0.9900
N1—C7	1.285 (4)	C9—H9B	0.9900
N1—C9'	1.505 (6)	C10—H10A	0.9900
N1—C9	1.524 (6)	C10—H10B	0.9900
N2—C11	1.455 (4)	C9'—C10'	1.503 (7)
N2—C14	1.462 (4)	C9'—H9C	0.9900
N2—C10	1.509 (6)	C9'—H9D	0.9900
N2—C10'	1.518 (6)	C10'—H10C	0.9900
N3—C13	1.474 (5)	C10'—H10D	0.9900
N3—C12	1.476 (5)	C11—C12	1.525 (4)
N3—H3A	0.918 (18)	C11—H11A	0.9900
N3—H3B	0.897 (18)	C11—H11B	0.9900
C1—C2	1.410 (4)	C12—H12A	0.9900
C1—C6	1.423 (4)	C12—H12B	0.9900
C2—C3	1.373 (5)	C13—C14	1.529 (5)
C2—H2	0.9500	C13—H13A	0.9900
C3—C4	1.388 (5)	C13—H13B	0.9900
C3—H3	0.9500	C14—H14A	0.9900
C4—C5	1.372 (4)	C14—H14B	0.9900
C5—C6	1.420 (4)
O1—Cd1—N1	82.23 (9)	O2—C8—H8A	109.5
O1—Cd1—Cl1	92.75 (6)	O2—C8—H8B	109.5
N1—Cd1—Cl1	135.90 (10)	H8A—C8—H8B	109.5
O1—Cd1—N2	153.88 (8)	O2—C8—H8C	109.5
N1—Cd1—N2	74.96 (9)	H8A—C8—H8C	109.5
Cl1—Cd1—N2	94.82 (6)	H8B—C8—H8C	109.5
O1—Cd1—Cl2	104.60 (6)	C10—C9—N1	107.9 (5)
N1—Cd1—Cl2	117.46 (9)	C10—C9—H9A	110.1
Cl1—Cd1—Cl2	106.24 (3)	N1—C9—H9A	110.1
N2—Cd1—Cl2	97.20 (7)	C10—C9—H9B	110.1
C1—O1—Cd1	129.33 (19)	N1—C9—H9B	110.1
C4—O2—C8	116.0 (2)	H9A—C9—H9B	108.4
C7—N1—C9'	118.1 (4)	C9—C10—N2	108.4 (5)
C7—N1—C9	116.0 (4)	C9—C10—H10A	110.0
C9'—N1—C9	29.7 (3)	N2—C10—H10A	110.0
C7—N1—Cd1	128.7 (2)	C9—C10—H10B	110.0
C9'—N1—Cd1	111.0 (3)	N2—C10—H10B	110.0
C9—N1—Cd1	113.8 (3)	H10A—C10—H10B	108.4
C11—N2—C14	107.8 (3)	C10'—C9'—N1	103.3 (5)
C11—N2—C10	126.5 (4)	C10'—C9'—H9C	111.1
C14—N2—C10	98.8 (4)	N1—C9'—H9C	111.1
C11—N2—C10'	98.2 (4)	C10'—C9'—H9D	111.1
C14—N2—C10'	127.0 (4)	N1—C9'—H9D	111.1
C10—N2—C10'	32.4 (3)	H9C—C9'—H9D	109.1
C11—N2—Cd1	111.46 (19)	C9'—C10'—N2	111.4 (6)
C14—N2—Cd1	108.48 (19)	C9'—C10'—H10C	109.3
C10—N2—Cd1	102.3 (3)	N2—C10'—H10C	109.3
C10'—N2—Cd1	103.2 (3)	C9'—C10'—H10D	109.3
C13—N3—C12	111.8 (3)	N2—C10'—H10D	109.3
C13—N3—H3A	113 (2)	H10C—C10'—H10D	108.0
C12—N3—H3A	110 (2)	N2—C11—C12	114.2 (3)
C13—N3—H3B	103 (2)	N2—C11—H11A	108.7
C12—N3—H3B	110 (2)	C12—C11—H11A	108.7
H3A—N3—H3B	109 (3)	N2—C11—H11B	108.7
O1—C1—C2	119.3 (3)	C12—C11—H11B	108.7
O1—C1—C6	124.9 (3)	H11A—C11—H11B	107.6
C2—C1—C6	115.7 (3)	N3—C12—C11	110.1 (3)
C3—C2—C1	123.2 (3)	N3—C12—H12A	109.6
C3—C2—H2	118.4	C11—C12—H12A	109.6
C1—C2—H2	118.4	N3—C12—H12B	109.6
C2—C3—C4	120.4 (3)	C11—C12—H12B	109.6
C2—C3—H3	119.8	H12A—C12—H12B	108.2
C4—C3—H3	119.8	N3—C13—C14	109.8 (3)
C5—C4—O2	125.2 (3)	N3—C13—H13A	109.7
C5—C4—C3	119.0 (3)	C14—C13—H13A	109.7
O2—C4—C3	115.8 (3)	N3—C13—H13B	109.7
C4—C5—C6	121.4 (3)	C14—C13—H13B	109.7
C4—C5—H5	119.3	H13A—C13—H13B	108.2
C6—C5—H5	119.3	N2—C14—C13	113.8 (3)
C5—C6—C1	120.0 (3)	N2—C14—H14A	108.8
C5—C6—C7	115.2 (3)	C13—C14—H14A	108.8
C1—C6—C7	124.8 (3)	N2—C14—H14B	108.8
N1—C7—C6	127.5 (3)	C13—C14—H14B	108.8
N1—C7—H7	116.3	H14A—C14—H14B	107.7
C6—C7—H7	116.3

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1i	0.92 (2)	1.80 (2)	2.705 (3)	166 (4)
N3—H3B···Cl2ii	0.90 (2)	2.33 (2)	3.222 (3)	174 (4)
C9—H9A···Cl1iii	0.99	2.64	3.454 (8)	139
C8—H8A···Cl2iv	0.98	2.82	3.777 (3)	167
C8—H8B···Cl1v	0.98	2.76	3.514 (3)	134
C13—H13A···Cl1i	0.99	2.71	3.542 (4)	142
C12—H12A···Cg1vi	0.99	2.48	3.408 (4)	156
C9'—H9D···Cg1iv	0.99	2.72	3.620 (8)	151

Table 1

Selected bond lengths (Å)

Cd1—O1	2.241 (2)
Cd1—N1	2.245 (3)
Cd1—N2	2.475 (2)
Cd1—Cl1	2.4584 (8)
Cd1—Cl2	2.4797 (8)

Table 2

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
N3—H3A⋯O1i	0.92 (2)	1.80 (2)	2.705 (3)	166 (4)
N3—H3B⋯Cl2ii	0.90 (2)	2.33 (2)	3.222 (3)	174 (4)
C9—H9A⋯Cl1iii	0.99	2.64	3.454 (8)	139
C8—H8A⋯Cl2iv	0.98	2.82	3.777 (3)	167
C8—H8B⋯Cl1v	0.98	2.76	3.514 (3)	134
C13—H13A⋯Cl1i	0.99	2.71	3.542 (4)	142
C12—H12A⋯Cg1vi	0.99	2.48	3.408 (4)	156
C9′—H9D⋯Cg1iv	0.99	2.72	3.620 (8)	151

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