Chlorido{4-chloro-2-[(2-morpholinoeth-yl)imino-meth-yl]phenolato-κN,N',O}copper(II).

The Cu(II) atom in the title compound, [Cu(C(13)H(16)ClN(2)O(2))Cl], exists in a distorted square-planar coordination environment as the deprotonated Schiff base chelates to the Cu(II) atom through three atom sites. In the crystal structure, adjacent mol-ecules are linked by a Cu⋯Cl [3.011 (1) Å] bridge, generating a linear chain running along the b axis of the ortho-rhom-bic unit cell.

Related literature

A similar deprotonated Schiff base is bidentate in bis­{5-meth­oxy-2-[(2-morpholinoeth­yl)imino­meth­yl]phenolato}nickel; see: Mohd Lair et al. (2009 ▶).

Experimental

Crystal data

[Cu(C13H16ClN2O2)Cl]

M = 366.72

Orthorhombic,

a = 23.0936 (6) Å

b = 8.4890 (2) Å

c = 14.0582 (3) Å

V = 2756.0 (1) Å3

Z = 8

Mo Kα radiation

μ = 1.97 mm−1

T = 140 K

0.40 × 0.10 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.506, T max = 0.962

17248 measured reflections

3156 independent reflections

2416 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.09

3156 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.76 e Å−3

Δρmin = −0.84 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025215/xu2547sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025215/xu2547Isup2.hkl

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

[Cu(C13H16ClN2O2)Cl]	F(000) = 1496
Mr = 366.72	Dx = 1.768 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4043 reflections
a = 23.0936 (6) Å	θ = 2.6–28.1°
b = 8.4890 (2) Å	µ = 1.97 mm−1
c = 14.0582 (3) Å	T = 140 K
V = 2756.0 (1) Å3	Plate, green
Z = 8	0.40 × 0.10 × 0.02 mm

Bruker SMART APEX diffractometer	3156 independent reflections
Radiation source: fine-focus sealed tube	2416 reflections with I > 2σ(I)
graphite	Rint = 0.050
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→30
Tmin = 0.506, Tmax = 0.962	k = −10→10
17248 measured reflections	l = −18→18

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0476P)2 + 6.7938P] where P = (Fo2 + 2Fc2)/3
3156 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.76 e Å−3
0 restraints	Δρmin = −0.84 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.229938 (18)	0.65838 (5)	0.49762 (3)	0.01385 (13)
Cl1	0.24525 (4)	0.85643 (10)	0.39295 (6)	0.0181 (2)
Cl2	0.43295 (4)	0.32750 (12)	0.83746 (7)	0.0253 (2)
O1	0.30890 (10)	0.6693 (3)	0.53670 (17)	0.0159 (5)
O2	0.03792 (12)	0.7569 (3)	0.36877 (18)	0.0225 (6)
N1	0.20874 (13)	0.5357 (3)	0.60938 (19)	0.0141 (6)
N2	0.14182 (13)	0.6347 (3)	0.46204 (19)	0.0131 (6)
C1	0.33436 (15)	0.5909 (4)	0.6049 (2)	0.0131 (7)
C2	0.39494 (16)	0.6087 (4)	0.6170 (2)	0.0158 (7)
H2	0.4156	0.6769	0.5756	0.019*
C3	0.42459 (16)	0.5294 (4)	0.6873 (2)	0.0157 (7)
H3	0.4652	0.5438	0.6942	0.019*
C4	0.39495 (16)	0.4279 (4)	0.7485 (2)	0.0169 (7)
C5	0.33647 (16)	0.4082 (4)	0.7404 (2)	0.0158 (7)
H5	0.3168	0.3396	0.7829	0.019*
C6	0.30502 (15)	0.4889 (4)	0.6696 (2)	0.0139 (7)
C7	0.24355 (16)	0.4685 (4)	0.6681 (2)	0.0149 (7)
H7	0.2271	0.3998	0.7141	0.018*
C8	0.14665 (15)	0.5035 (4)	0.6176 (2)	0.0147 (7)
H8A	0.1272	0.5891	0.6531	0.018*
H8B	0.1401	0.4030	0.6517	0.018*
C9	0.12305 (15)	0.4933 (4)	0.5171 (2)	0.0147 (7)
H9A	0.1376	0.3966	0.4859	0.018*
H9B	0.0802	0.4882	0.5189	0.018*
C10	0.11098 (16)	0.7815 (4)	0.4921 (2)	0.0168 (7)
H10A	0.1293	0.8732	0.4607	0.020*
H10B	0.1155	0.7949	0.5617	0.020*
C11	0.04724 (17)	0.7799 (5)	0.4681 (3)	0.0209 (8)
H11A	0.0280	0.6943	0.5040	0.025*
H11B	0.0296	0.8810	0.4879	0.025*
C12	0.06457 (16)	0.6146 (5)	0.3373 (3)	0.0202 (8)
H12A	0.0585	0.6029	0.2679	0.024*
H12B	0.0459	0.5239	0.3693	0.024*
C13	0.12914 (16)	0.6129 (5)	0.3585 (2)	0.0173 (7)
H13A	0.1457	0.5114	0.3371	0.021*
H13B	0.1482	0.6981	0.3220	0.021*

	U11	U22	U33	U12	U13	U23
Cu1	0.0132 (2)	0.0170 (2)	0.0113 (2)	−0.00069 (18)	−0.00083 (15)	0.00270 (17)
Cl1	0.0202 (4)	0.0186 (4)	0.0154 (4)	−0.0010 (4)	−0.0009 (3)	0.0058 (3)
Cl2	0.0222 (5)	0.0295 (5)	0.0243 (5)	−0.0005 (4)	−0.0077 (4)	0.0126 (4)
O1	0.0146 (13)	0.0158 (13)	0.0174 (11)	0.0000 (10)	−0.0020 (10)	0.0069 (10)
O2	0.0209 (14)	0.0274 (15)	0.0193 (13)	0.0077 (12)	−0.0033 (11)	0.0008 (11)
N1	0.0152 (15)	0.0145 (15)	0.0126 (13)	−0.0010 (12)	−0.0018 (11)	−0.0015 (11)
N2	0.0163 (15)	0.0126 (14)	0.0103 (12)	0.0011 (12)	−0.0014 (11)	−0.0013 (11)
C1	0.0171 (18)	0.0117 (17)	0.0106 (15)	0.0007 (14)	−0.0021 (13)	−0.0006 (12)
C2	0.0173 (19)	0.0149 (17)	0.0151 (16)	−0.0030 (15)	0.0029 (13)	−0.0001 (13)
C3	0.0154 (18)	0.0144 (18)	0.0173 (16)	−0.0016 (14)	−0.0018 (13)	−0.0031 (13)
C4	0.0221 (19)	0.0159 (18)	0.0126 (15)	0.0024 (15)	−0.0035 (14)	0.0028 (13)
C5	0.0225 (19)	0.0127 (18)	0.0121 (15)	0.0002 (15)	0.0005 (13)	0.0006 (13)
C6	0.0191 (18)	0.0119 (16)	0.0106 (15)	0.0005 (14)	0.0001 (13)	−0.0007 (12)
C7	0.0205 (19)	0.0142 (17)	0.0100 (14)	0.0009 (14)	0.0029 (13)	−0.0002 (13)
C8	0.0140 (17)	0.0166 (17)	0.0133 (15)	−0.0007 (14)	−0.0002 (13)	0.0032 (13)
C9	0.0146 (17)	0.0161 (17)	0.0135 (16)	0.0003 (14)	−0.0030 (12)	0.0022 (13)
C10	0.0194 (18)	0.0146 (17)	0.0164 (16)	0.0035 (15)	0.0008 (14)	−0.0009 (14)
C11	0.022 (2)	0.0218 (19)	0.0191 (17)	0.0042 (17)	0.0028 (15)	−0.0031 (15)
C12	0.020 (2)	0.0238 (19)	0.0171 (17)	0.0009 (16)	−0.0031 (14)	−0.0020 (15)
C13	0.0191 (19)	0.0198 (18)	0.0130 (15)	0.0019 (15)	−0.0011 (13)	−0.0012 (14)

Cu1—O1	1.907 (2)	C4—C5	1.366 (5)
Cu1—N1	1.947 (3)	C5—C6	1.410 (5)
Cu1—N2	2.105 (3)	C5—H5	0.9500
Cu1—Cl1	2.2620 (9)	C6—C7	1.430 (5)
Cu1—Cl1i	3.0107 (10)	C7—H7	0.9500
Cl2—C4	1.750 (3)	C8—C9	1.516 (4)
O1—C1	1.307 (4)	C8—H8A	0.9900
O2—C11	1.427 (4)	C8—H8B	0.9900
O2—C12	1.426 (5)	C9—H9A	0.9900
N1—C7	1.285 (4)	C9—H9B	0.9900
N1—C8	1.464 (4)	C10—C11	1.510 (5)
N2—C9	1.492 (4)	C10—H10A	0.9900
N2—C13	1.496 (4)	C10—H10B	0.9900
N2—C10	1.497 (4)	C11—H11A	0.9900
C1—C2	1.417 (5)	C11—H11B	0.9900
C1—C6	1.427 (5)	C12—C13	1.521 (5)
C2—C3	1.378 (5)	C12—H12A	0.9900
C2—H2	0.9500	C12—H12B	0.9900
C3—C4	1.396 (5)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
O1—Cu1—N1	91.95 (11)	N1—C7—C6	125.2 (3)
O1—Cu1—N2	176.00 (11)	N1—C7—H7	117.4
N1—Cu1—N2	84.12 (12)	C6—C7—H7	117.4
O1—Cu1—Cl1	90.10 (7)	N1—C8—C9	106.8 (3)
N1—Cu1—Cl1	164.06 (9)	N1—C8—H8A	110.4
N2—Cu1—Cl1	93.88 (8)	C9—C8—H8A	110.4
O1—Cu1—Cl1i	90.02 (8)	N1—C8—H8B	110.4
N1—Cu1—Cl1i	89.25 (9)	C9—C8—H8B	110.4
N2—Cu1—Cl1i	89.22 (8)	H8A—C8—H8B	108.6
Cl1—Cu1—Cl1i	106.56 (3)	N2—C9—C8	109.5 (3)
C1—O1—Cu1	128.1 (2)	N2—C9—H9A	109.8
C11—O2—C12	110.8 (3)	C8—C9—H9A	109.8
C7—N1—C8	118.6 (3)	N2—C9—H9B	109.8
C7—N1—Cu1	126.7 (3)	C8—C9—H9B	109.8
C8—N1—Cu1	114.2 (2)	H9A—C9—H9B	108.2
C9—N2—C13	110.4 (3)	N2—C10—C11	113.1 (3)
C9—N2—C10	112.6 (3)	N2—C10—H10A	109.0
C13—N2—C10	106.5 (3)	C11—C10—H10A	109.0
C9—N2—Cu1	103.6 (2)	N2—C10—H10B	109.0
C13—N2—Cu1	115.6 (2)	C11—C10—H10B	109.0
C10—N2—Cu1	108.2 (2)	H10A—C10—H10B	107.8
O1—C1—C2	118.5 (3)	O2—C11—C10	111.5 (3)
O1—C1—C6	124.3 (3)	O2—C11—H11A	109.3
C2—C1—C6	117.2 (3)	C10—C11—H11A	109.3
C3—C2—C1	121.6 (3)	O2—C11—H11B	109.3
C3—C2—H2	119.2	C10—C11—H11B	109.3
C1—C2—H2	119.2	H11A—C11—H11B	108.0
C2—C3—C4	120.0 (3)	O2—C12—C13	111.7 (3)
C2—C3—H3	120.0	O2—C12—H12A	109.3
C4—C3—H3	120.0	C13—C12—H12A	109.3
C5—C4—C3	120.6 (3)	O2—C12—H12B	109.3
C5—C4—Cl2	119.7 (3)	C13—C12—H12B	109.3
C3—C4—Cl2	119.7 (3)	H12A—C12—H12B	107.9
C4—C5—C6	120.5 (3)	N2—C13—C12	112.4 (3)
C4—C5—H5	119.7	N2—C13—H13A	109.1
C6—C5—H5	119.7	C12—C13—H13A	109.1
C5—C6—C7	117.6 (3)	N2—C13—H13B	109.1
C5—C6—C1	120.0 (3)	C12—C13—H13B	109.1
C7—C6—C1	122.4 (3)	H13A—C13—H13B	107.8
N1—Cu1—O1—C1	11.0 (3)	Cl2—C4—C5—C6	179.6 (3)
Cl1—Cu1—O1—C1	175.2 (3)	C4—C5—C6—C7	−177.2 (3)
Cl1i—Cu1—O1—C1	−78.2 (3)	C4—C5—C6—C1	0.6 (5)
O1—Cu1—N1—C7	−12.6 (3)	O1—C1—C6—C5	179.4 (3)
N2—Cu1—N1—C7	166.6 (3)	C2—C1—C6—C5	−1.3 (5)
Cl1—Cu1—N1—C7	−109.8 (4)	O1—C1—C6—C7	−2.9 (5)
Cl1i—Cu1—N1—C7	77.4 (3)	C2—C1—C6—C7	176.3 (3)
O1—Cu1—N1—C8	175.5 (2)	C8—N1—C7—C6	−179.5 (3)
N2—Cu1—N1—C8	−5.2 (2)	Cu1—N1—C7—C6	9.0 (5)
Cl1—Cu1—N1—C8	78.3 (4)	C5—C6—C7—N1	178.7 (3)
Cl1i—Cu1—N1—C8	−94.5 (2)	C1—C6—C7—N1	1.0 (5)
N1—Cu1—N2—C9	−21.8 (2)	C7—N1—C8—C9	−141.6 (3)
Cl1—Cu1—N2—C9	174.03 (19)	Cu1—N1—C8—C9	30.9 (3)
Cl1i—Cu1—N2—C9	67.48 (19)	C13—N2—C9—C8	169.0 (3)
N1—Cu1—N2—C13	−142.8 (3)	C10—N2—C9—C8	−72.1 (3)
Cl1—Cu1—N2—C13	53.1 (2)	Cu1—N2—C9—C8	44.6 (3)
Cl1i—Cu1—N2—C13	−53.4 (2)	N1—C8—C9—N2	−50.7 (4)
N1—Cu1—N2—C10	97.9 (2)	C9—N2—C10—C11	−67.4 (4)
Cl1—Cu1—N2—C10	−66.2 (2)	C13—N2—C10—C11	53.8 (4)
Cl1i—Cu1—N2—C10	−172.8 (2)	Cu1—N2—C10—C11	178.7 (2)
Cu1—O1—C1—C2	175.2 (2)	C12—O2—C11—C10	57.0 (4)
Cu1—O1—C1—C6	−5.6 (5)	N2—C10—C11—O2	−57.2 (4)
O1—C1—C2—C3	−179.9 (3)	C11—O2—C12—C13	−57.2 (4)
C6—C1—C2—C3	0.8 (5)	C9—N2—C13—C12	69.1 (4)
C1—C2—C3—C4	0.4 (5)	C10—N2—C13—C12	−53.5 (4)
C2—C3—C4—C5	−1.2 (5)	Cu1—N2—C13—C12	−173.8 (2)
C2—C3—C4—Cl2	179.9 (3)	O2—C12—C13—N2	57.4 (4)
C3—C4—C5—C6	0.7 (5)

Table 1

Selected bond lengths (Å)

Cu1—O1	1.907 (2)
Cu1—N1	1.947 (3)
Cu1—N2	2.105 (3)
Cu1—Cl1	2.2620 (9)