Dichloro­{4-chloro-2-[2-(diethyl­ammonio)­ethyl­iminometh­yl]phenolato-κ²N,O}copper(II)

The title compound, [CuCl₂(C₁₃H₁₉ClN₂O)], is a mononuclear copper(II) complex. The Cu^II ion is four-coordinated by the phenolate O and the imine N atoms of the Schiff base ligand, and by two Cl atoms, forming a distorted tetra­hedral geometry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.045
• wR factor = 0.096
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Dichloro{4-chloro-2-[(2-diethylaminoethylimino)methyl]phenolato- κ²N,O}copper(II)

Crystal data

[CuCl2(C13H19ClN2O)]	F(000) = 796
Mr = 389.19	Dx = 1.570 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1888 reflections
a = 6.924 (1) Å	θ = 2.4–24.3°
b = 15.293 (2) Å	µ = 1.81 mm^−1
c = 15.904 (2) Å	T = 298 K
β = 102.072 (2)°	Block, blue
V = 1646.8 (4) Å^3	0.11 × 0.09 × 0.07 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3749 independent reflections
Radiation source: fine-focus sealed tube	2607 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.826, Tmax = 0.884	k = −19→19
13931 measured reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0336P)^2] where P = (Fo^2 + 2Fc^2)/3
3749 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.33 e Å^−3
1 restraint	Δρmin = −0.29 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.45571 (5)	0.88196 (2)	0.27114 (3)	0.03576 (13)
Cl1	−0.11288 (15)	0.62445 (6)	0.50563 (7)	0.0644 (3)
Cl2	0.55468 (15)	0.91103 (6)	0.15209 (6)	0.0584 (3)
Cl3	0.63439 (12)	0.96258 (6)	0.38352 (6)	0.0467 (2)
O1	0.4418 (3)	0.76296 (14)	0.30719 (15)	0.0451 (6)
N1	0.1721 (4)	0.91185 (16)	0.27253 (16)	0.0344 (6)
N2	0.2642 (4)	1.09111 (16)	0.34421 (16)	0.0325 (6)
C1	0.1348 (4)	0.78085 (19)	0.35484 (19)	0.0324 (7)
C2	0.3116 (4)	0.7348 (2)	0.34905 (19)	0.0352 (7)
C3	0.3416 (5)	0.6529 (2)	0.3903 (2)	0.0399 (8)
H3	0.4512	0.6200	0.3849	0.048*
C4	0.2154 (5)	0.6202 (2)	0.4380 (2)	0.0413 (8)
H4	0.2419	0.5666	0.4657	0.050*
C5	0.0481 (5)	0.6667 (2)	0.4451 (2)	0.0396 (8)
C6	0.0066 (5)	0.7443 (2)	0.4035 (2)	0.0388 (8)
H6	−0.1088	0.7739	0.4071	0.047*
C7	0.0728 (4)	0.86161 (19)	0.31179 (19)	0.0344 (7)
H7	−0.0552	0.8796	0.3125	0.041*
C8	0.0732 (5)	0.9901 (2)	0.2302 (2)	0.0402 (8)
H8A	−0.0503	0.9987	0.2487	0.048*
H8B	0.0427	0.9810	0.1685	0.048*
C9	0.1989 (5)	1.0713 (2)	0.25053 (19)	0.0375 (8)
H9A	0.3151	1.0648	0.2260	0.045*
H9B	0.1247	1.1209	0.2226	0.045*
C10	0.3865 (5)	1.1736 (2)	0.3547 (2)	0.0438 (8)
H10A	0.4879	1.1685	0.3212	0.053*
H10B	0.3025	1.2226	0.3322	0.053*
C11	0.4828 (5)	1.1920 (2)	0.4468 (2)	0.0527 (10)
H11A	0.3831	1.2046	0.4789	0.079*
H11B	0.5696	1.2413	0.4493	0.079*
H11C	0.5573	1.1417	0.4711	0.079*
C12	0.1005 (5)	1.0922 (2)	0.3928 (2)	0.0425 (8)
H12A	0.1573	1.1002	0.4535	0.051*
H12B	0.0350	1.0358	0.3862	0.051*
C13	−0.0509 (5)	1.1623 (3)	0.3644 (3)	0.0642 (11)
H13A	0.0123	1.2185	0.3707	0.096*
H13B	−0.1487	1.1601	0.3992	0.096*
H13C	−0.1133	1.1531	0.3053	0.096*
H2	0.355 (4)	1.0501 (18)	0.365 (2)	0.080 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0322 (2)	0.0352 (2)	0.0416 (2)	0.00057 (17)	0.01175 (17)	0.00010 (18)
Cl1	0.0655 (6)	0.0596 (6)	0.0739 (7)	−0.0079 (5)	0.0281 (5)	0.0191 (5)
Cl2	0.0703 (7)	0.0623 (6)	0.0487 (5)	−0.0095 (5)	0.0265 (5)	−0.0020 (5)
Cl3	0.0373 (5)	0.0507 (5)	0.0490 (5)	0.0032 (4)	0.0020 (4)	−0.0044 (4)
O1	0.0442 (13)	0.0372 (13)	0.0605 (15)	0.0044 (11)	0.0264 (12)	0.0006 (12)
N1	0.0327 (14)	0.0315 (14)	0.0368 (15)	−0.0002 (11)	0.0021 (12)	0.0017 (12)
N2	0.0305 (14)	0.0300 (14)	0.0358 (15)	−0.0013 (11)	0.0043 (12)	0.0039 (12)
C1	0.0351 (17)	0.0283 (16)	0.0333 (17)	0.0004 (13)	0.0060 (14)	−0.0037 (13)
C2	0.0379 (18)	0.0323 (17)	0.0336 (18)	−0.0008 (14)	0.0034 (14)	−0.0080 (14)
C3	0.0412 (19)	0.0314 (17)	0.046 (2)	0.0050 (15)	0.0055 (16)	−0.0027 (15)
C4	0.050 (2)	0.0311 (17)	0.0396 (19)	−0.0040 (16)	0.0010 (16)	0.0013 (15)
C5	0.046 (2)	0.0351 (18)	0.0373 (19)	−0.0096 (15)	0.0083 (15)	0.0010 (15)
C6	0.0377 (18)	0.0363 (18)	0.0416 (19)	−0.0017 (15)	0.0061 (15)	−0.0072 (15)
C7	0.0282 (16)	0.0384 (18)	0.0361 (18)	0.0005 (13)	0.0058 (14)	−0.0063 (14)
C8	0.0436 (19)	0.0348 (18)	0.0377 (19)	0.0033 (15)	−0.0016 (15)	0.0017 (15)
C9	0.0464 (19)	0.0342 (18)	0.0319 (18)	0.0047 (15)	0.0082 (15)	0.0070 (14)
C10	0.0423 (19)	0.0379 (19)	0.052 (2)	−0.0109 (15)	0.0112 (17)	0.0003 (16)
C11	0.051 (2)	0.054 (2)	0.051 (2)	−0.0133 (18)	0.0054 (18)	−0.0128 (18)
C12	0.0380 (19)	0.055 (2)	0.0360 (19)	−0.0063 (16)	0.0114 (15)	0.0012 (16)
C13	0.049 (2)	0.072 (3)	0.074 (3)	0.008 (2)	0.017 (2)	−0.008 (2)

Geometric parameters (Å, º)

Cu1—O1	1.916 (2)	C5—C6	1.360 (4)
Cu1—N1	2.021 (3)	C6—H6	0.9300
Cu1—Cl2	2.190 (2)	C7—H7	0.9300
Cu1—Cl3	2.306 (2)	C8—C9	1.512 (4)
Cl1—C5	1.743 (3)	C8—H8A	0.9700
O1—C2	1.301 (4)	C8—H8B	0.9700
N1—C7	1.278 (4)	C9—H9A	0.9700
N1—C8	1.470 (4)	C9—H9B	0.9700
N2—C9	1.495 (4)	C10—C11	1.504 (4)
N2—C12	1.500 (4)	C10—H10A	0.9700
N2—C10	1.509 (4)	C10—H10B	0.9700
N2—H2	0.90 (3)	C11—H11A	0.9600
C1—C6	1.409 (4)	C11—H11B	0.9600
C1—C2	1.432 (4)	C11—H11C	0.9600
C1—C7	1.434 (4)	C12—C13	1.502 (5)
C2—C3	1.408 (4)	C12—H12A	0.9700
C3—C4	1.366 (4)	C12—H12B	0.9700
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.384 (4)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
O1—Cu1—N1	95.85 (10)	N1—C8—C9	112.3 (3)
O1—Cu1—Cl2	119.72 (8)	N1—C8—H8A	109.2
N1—Cu1—Cl2	116.37 (8)	C9—C8—H8A	109.2
O1—Cu1—Cl3	109.15 (8)	N1—C8—H8B	109.2
N1—Cu1—Cl3	103.63 (7)	C9—C8—H8B	109.2
Cl2—Cu1—Cl3	110.33 (4)	H8A—C8—H8B	107.9
C2—O1—Cu1	123.45 (19)	N2—C9—C8	114.8 (3)
C7—N1—C8	117.8 (3)	N2—C9—H9A	108.6
C7—N1—Cu1	119.5 (2)	C8—C9—H9A	108.6
C8—N1—Cu1	122.7 (2)	N2—C9—H9B	108.6
C9—N2—C12	114.4 (3)	C8—C9—H9B	108.6
C9—N2—C10	109.0 (2)	H9A—C9—H9B	107.5
C12—N2—C10	113.6 (2)	C11—C10—N2	112.9 (3)
C9—N2—H2	106 (2)	C11—C10—H10A	109.0
C12—N2—H2	111 (2)	N2—C10—H10A	109.0
C10—N2—H2	102 (2)	C11—C10—H10B	109.0
C6—C1—C2	119.0 (3)	N2—C10—H10B	109.0
C6—C1—C7	116.3 (3)	H10A—C10—H10B	107.8
C2—C1—C7	124.6 (3)	C10—C11—H11A	109.5
O1—C2—C3	118.9 (3)	C10—C11—H11B	109.5
O1—C2—C1	124.2 (3)	H11A—C11—H11B	109.5
C3—C2—C1	116.9 (3)	C10—C11—H11C	109.5
C4—C3—C2	122.4 (3)	H11A—C11—H11C	109.5
C4—C3—H3	118.8	H11B—C11—H11C	109.5
C2—C3—H3	118.8	N2—C12—C13	114.1 (3)
C3—C4—C5	119.9 (3)	N2—C12—H12A	108.7
C3—C4—H4	120.0	C13—C12—H12A	108.7
C5—C4—H4	120.0	N2—C12—H12B	108.7
C6—C5—C4	120.3 (3)	C13—C12—H12B	108.7
C6—C5—Cl1	119.9 (3)	H12A—C12—H12B	107.6
C4—C5—Cl1	119.8 (3)	C12—C13—H13A	109.5
C5—C6—C1	121.3 (3)	C12—C13—H13B	109.5
C5—C6—H6	119.4	H13A—C13—H13B	109.5
C1—C6—H6	119.4	C12—C13—H13C	109.5
N1—C7—C1	127.8 (3)	H13A—C13—H13C	109.5
N1—C7—H7	116.1	H13B—C13—H13C	109.5
C1—C7—H7	116.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl3	0.90 (3)	2.32 (2)	3.187 (3)	161 (3)