Chlorido(2-{1-[(2-morpholino-eth-yl)imino]-eth-yl}phenolato-κN,N',O)copper(II).

In the title compound, [CuCl(C(14)H(19)N(2)O(2))], the Cu(II) ion is four-coordinated by one deprotonated N,N',O-tridentate Schiff base and one chloride ion in a distorted square-planar geometry. In the crystal, adjacent mol-ecules are linked via C-H⋯Cl and C-H⋯O inter-actions, forming infinite layers parallel to the (100) plane. The structure was determined from a non-merohedrally twined crystal [twin ratio 0.777 (3):0.223 (3)].

Related literature

For the crystal structures of similar CuII complexes, see: Elias et al. (1982 ▶); Ikmal Hisham et al. (2009 ▶); Wang & You (2007 ▶).

Experimental

Crystal data

[CuCl(C14H19N2O2)]

M = 346.30

Monoclinic,

a = 10.7122 (4) Å

b = 17.1657 (7) Å

c = 7.7638 (3) Å

β = 93.493 (3)°

V = 1424.97 (10) Å3

Z = 4

Mo Kα radiation

μ = 1.72 mm−1

T = 100 K

0.31 × 0.22 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.617, T max = 0.889

10834 measured reflections

2506 independent reflections

2313 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.096

S = 1.10

2506 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −1.15 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/S1600536810051160/gk2329sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051160/gk2329Isup2.hkl

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

[CuCl(C14H19N2O2)]	F(000) = 716
Mr = 346.30	Dx = 1.614 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4663 reflections
a = 10.7122 (4) Å	θ = 2.4–28.8°
b = 17.1657 (7) Å	µ = 1.72 mm−1
c = 7.7638 (3) Å	T = 100 K
β = 93.493 (3)°	Plate, blue
V = 1424.97 (10) Å3	0.31 × 0.22 × 0.07 mm
Z = 4

Bruker APEXII CCD diffractometer	2506 independent reflections
Radiation source: fine-focus sealed tube	2313 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.617, Tmax = 0.889	k = −20→20
10834 measured reflections	l = −6→9

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.P)2 + 6.7834P] where P = (Fo2 + 2Fc2)/3
2506 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −1.15 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
Cu1	0.51091 (4)	0.13385 (3)	0.49248 (6)	0.01131 (15)
Cl1	0.35700 (9)	0.11054 (6)	0.28748 (12)	0.0166 (2)
O1	0.6167 (3)	0.17572 (17)	0.3321 (4)	0.0177 (6)
O2	0.1491 (3)	0.09423 (18)	0.8080 (4)	0.0209 (7)
N1	0.6497 (3)	0.1116 (2)	0.6556 (4)	0.0152 (8)
N2	0.3974 (3)	0.12315 (19)	0.6943 (4)	0.0125 (7)
C1	0.7370 (4)	0.1654 (2)	0.3291 (5)	0.0138 (8)
C2	0.7957 (4)	0.1964 (2)	0.1849 (6)	0.0169 (9)
H2	0.7470	0.2253	0.1008	0.020*
C3	0.9208 (4)	0.1858 (2)	0.1639 (6)	0.0195 (10)
H3	0.9571	0.2063	0.0648	0.023*
C4	0.9953 (4)	0.1448 (3)	0.2879 (6)	0.0224 (10)
H4	1.0816	0.1365	0.2722	0.027*
C5	0.9423 (4)	0.1168 (2)	0.4322 (6)	0.0168 (9)
H5	0.9939	0.0903	0.5173	0.020*
C6	0.8129 (4)	0.1261 (2)	0.4589 (5)	0.0140 (8)
C7	0.7669 (4)	0.1010 (2)	0.6241 (6)	0.0141 (9)
C8	0.8561 (4)	0.0640 (3)	0.7551 (6)	0.0217 (10)
H8A	0.8092	0.0353	0.8391	0.033*
H8B	0.9068	0.1044	0.8148	0.033*
H8C	0.9110	0.0279	0.6974	0.033*
C9	0.6058 (4)	0.0955 (3)	0.8300 (5)	0.0171 (9)
H9A	0.6696	0.1123	0.9199	0.021*
H9B	0.5911	0.0389	0.8440	0.021*
C10	0.4853 (4)	0.1402 (3)	0.8475 (6)	0.0206 (9)
H10A	0.4467	0.1245	0.9549	0.025*
H10B	0.5030	0.1967	0.8539	0.025*
C11	0.3417 (4)	0.0438 (2)	0.6993 (5)	0.0122 (8)
H11A	0.4089	0.0052	0.7246	0.015*
H11B	0.3010	0.0313	0.5847	0.015*
C12	0.2454 (4)	0.0379 (2)	0.8359 (5)	0.0170 (9)
H12A	0.2082	−0.0149	0.8327	0.020*
H12B	0.2875	0.0457	0.9517	0.020*
C13	0.2030 (4)	0.1704 (3)	0.8178 (6)	0.0204 (10)
H13A	0.2462	0.1780	0.9329	0.025*
H13B	0.1359	0.2100	0.8033	0.025*
C14	0.2951 (4)	0.1817 (2)	0.6801 (6)	0.0187 (9)
H14A	0.2506	0.1775	0.5649	0.022*
H14B	0.3315	0.2346	0.6906	0.022*

	U11	U22	U33	U12	U13	U23
Cu1	0.0114 (3)	0.0124 (2)	0.0102 (2)	−0.0004 (2)	0.00097 (19)	0.00130 (19)
Cl1	0.0189 (5)	0.0203 (5)	0.0101 (5)	−0.0007 (4)	−0.0027 (4)	0.0009 (4)
O1	0.0153 (15)	0.0196 (16)	0.0184 (16)	−0.0014 (12)	0.0031 (12)	0.0058 (13)
O2	0.0119 (15)	0.0287 (17)	0.0220 (17)	0.0000 (13)	0.0014 (13)	0.0008 (14)
N1	0.0170 (18)	0.0164 (18)	0.0122 (18)	−0.0036 (14)	0.0004 (15)	0.0011 (14)
N2	0.0171 (17)	0.0128 (17)	0.0073 (17)	−0.0002 (14)	−0.0006 (13)	0.0012 (13)
C1	0.015 (2)	0.0110 (19)	0.015 (2)	−0.0025 (16)	0.0002 (16)	−0.0040 (16)
C2	0.022 (2)	0.012 (2)	0.017 (2)	−0.0015 (17)	0.0020 (18)	0.0000 (17)
C3	0.025 (2)	0.016 (2)	0.018 (2)	−0.0056 (18)	0.0070 (18)	−0.0009 (18)
C4	0.016 (2)	0.020 (2)	0.032 (3)	−0.0030 (18)	0.0042 (19)	−0.004 (2)
C5	0.015 (2)	0.014 (2)	0.021 (2)	0.0006 (16)	0.0000 (18)	−0.0024 (17)
C6	0.016 (2)	0.011 (2)	0.015 (2)	0.0001 (16)	0.0013 (17)	−0.0023 (16)
C7	0.015 (2)	0.0091 (19)	0.018 (2)	−0.0009 (16)	−0.0015 (17)	−0.0016 (16)
C8	0.013 (2)	0.031 (3)	0.021 (2)	0.0014 (19)	0.0002 (18)	0.006 (2)
C9	0.018 (2)	0.026 (2)	0.007 (2)	−0.0061 (18)	−0.0030 (17)	0.0033 (17)
C10	0.020 (2)	0.022 (2)	0.020 (2)	−0.0029 (19)	0.0016 (19)	−0.0059 (19)
C11	0.017 (2)	0.0096 (19)	0.010 (2)	−0.0004 (16)	0.0003 (16)	0.0004 (15)
C12	0.018 (2)	0.020 (2)	0.014 (2)	−0.0048 (17)	−0.0005 (17)	0.0006 (17)
C13	0.017 (2)	0.022 (2)	0.022 (2)	0.0066 (18)	0.0015 (18)	−0.0004 (19)
C14	0.026 (2)	0.013 (2)	0.016 (2)	0.0030 (18)	0.0002 (18)	0.0008 (17)

Cu1—O1	1.877 (3)	C5—H5	0.9500
Cu1—N1	1.932 (3)	C6—C7	1.466 (6)
Cu1—N2	2.050 (3)	C7—C8	1.495 (6)
Cu1—Cl1	2.2565 (11)	C8—H8A	0.9800
O1—C1	1.302 (5)	C8—H8B	0.9800
O2—C12	1.422 (5)	C8—H8C	0.9800
O2—C13	1.430 (5)	C9—C10	1.515 (6)
N1—C7	1.306 (5)	C9—H9A	0.9900
N1—C9	1.486 (5)	C9—H9B	0.9900
N2—C14	1.485 (5)	C10—H10A	0.9900
N2—C11	1.488 (5)	C10—H10B	0.9900
N2—C10	1.500 (5)	C11—C12	1.527 (6)
C1—C2	1.421 (6)	C11—H11A	0.9900
C1—C6	1.426 (6)	C11—H11B	0.9900
C2—C3	1.373 (6)	C12—H12A	0.9900
C2—H2	0.9500	C12—H12B	0.9900
C3—C4	1.401 (6)	C13—C14	1.511 (6)
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.374 (6)	C13—H13B	0.9900
C4—H4	0.9500	C14—H14A	0.9900
C5—C6	1.423 (6)	C14—H14B	0.9900
O1—Cu1—N1	92.21 (14)	H8A—C8—H8B	109.5
O1—Cu1—N2	162.15 (13)	C7—C8—H8C	109.5
N1—Cu1—N2	87.14 (14)	H8A—C8—H8C	109.5
O1—Cu1—Cl1	92.57 (10)	H8B—C8—H8C	109.5
N1—Cu1—Cl1	158.07 (11)	N1—C9—C10	107.8 (3)
N2—Cu1—Cl1	94.66 (10)	N1—C9—H9A	110.1
C1—O1—Cu1	126.7 (3)	C10—C9—H9A	110.1
C12—O2—C13	109.1 (3)	N1—C9—H9B	110.1
C7—N1—C9	120.4 (4)	C10—C9—H9B	110.1
C7—N1—Cu1	127.9 (3)	H9A—C9—H9B	108.5
C9—N1—Cu1	111.1 (3)	N2—C10—C9	109.1 (3)
C14—N2—C11	109.0 (3)	N2—C10—H10A	109.9
C14—N2—C10	110.6 (3)	C9—C10—H10A	109.9
C11—N2—C10	113.0 (3)	N2—C10—H10B	109.9
C14—N2—Cu1	110.6 (2)	C9—C10—H10B	109.9
C11—N2—Cu1	111.1 (2)	H10A—C10—H10B	108.3
C10—N2—Cu1	102.4 (2)	N2—C11—C12	111.6 (3)
O1—C1—C2	116.7 (4)	N2—C11—H11A	109.3
O1—C1—C6	125.1 (4)	C12—C11—H11A	109.3
C2—C1—C6	118.2 (4)	N2—C11—H11B	109.3
C3—C2—C1	121.8 (4)	C12—C11—H11B	109.3
C3—C2—H2	119.1	H11A—C11—H11B	108.0
C1—C2—H2	119.1	O2—C12—C11	111.3 (3)
C2—C3—C4	120.3 (4)	O2—C12—H12A	109.4
C2—C3—H3	119.9	C11—C12—H12A	109.4
C4—C3—H3	119.9	O2—C12—H12B	109.4
C5—C4—C3	119.3 (4)	C11—C12—H12B	109.4
C5—C4—H4	120.3	H12A—C12—H12B	108.0
C3—C4—H4	120.3	O2—C13—C14	111.0 (4)
C4—C5—C6	122.3 (4)	O2—C13—H13A	109.4
C4—C5—H5	118.9	C14—C13—H13A	109.4
C6—C5—H5	118.9	O2—C13—H13B	109.4
C5—C6—C1	118.0 (4)	C14—C13—H13B	109.4
C5—C6—C7	118.5 (4)	H13A—C13—H13B	108.0
C1—C6—C7	123.3 (4)	N2—C14—C13	111.8 (3)
N1—C7—C6	120.1 (4)	N2—C14—H14A	109.3
N1—C7—C8	120.9 (4)	C13—C14—H14A	109.3
C6—C7—C8	119.0 (4)	N2—C14—H14B	109.3
C7—C8—H8A	109.5	C13—C14—H14B	109.3
C7—C8—H8B	109.5	H14A—C14—H14B	107.9

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···Cl1	0.99	2.75	3.386 (4)	123
C11—H11B···Cl1	0.99	2.78	3.409 (4)	122
C14—H14B···Cl1i	0.99	2.77	3.713 (4)	159
C10—H10B···O1i	0.99	2.52	3.465 (5)	160
C9—H9B···Cl1ii	0.99	2.83	3.680 (5)	144

Cu1—O1	1.877 (3)
Cu1—N1	1.932 (3)
Cu1—N2	2.050 (3)
Cu1—Cl1	2.2565 (11)

O1—Cu1—N1	92.21 (14)
O1—Cu1—N2	162.15 (13)
N1—Cu1—N2	87.14 (14)
O1—Cu1—Cl1	92.57 (10)
N1—Cu1—Cl1	158.07 (11)
N2—Cu1—Cl1	94.66 (10)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯Cl1	0.99	2.75	3.386 (4)	123
C11—H11B⋯Cl1	0.99	2.78	3.409 (4)	122
C14—H14B⋯Cl1i	0.99	2.77	3.713 (4)	159
C10—H10B⋯O1i	0.99	2.52	3.465 (5)	160
C9—H9B⋯Cl1ii	0.99	2.83	3.680 (5)	144

Symmetry codes: (i) ; (ii) .