Di-μ-chlorido-bis-[chlorido(N,N'-dibenzyl-propane-1,2-diamine-κN,N')copper(II)].

In the title complex, [Cu(2)Cl(4)(C(17)H(22)N(2))(2)], the Cu(II) cation is coordinated by a N,N'-dibenzyl-propane-1,2-diamine ligand and two Cl(-) anions, and a Cl(-) anion from an adjacent mol-ecule further bridges to the Cu(II) cation in the apical position, with a longer Cu-Cl distance of 2.9858 (18) Å, forming a centrosymmetric dimeric complex in which each Cu(II) cation is in a distorted square-pyramidal geometry. Intra-molecular N-H⋯Cl hydrogen bonding is observed in the dimeric complex.

Related literature

For Cu—Cl bond distances, see: Alves et al. (2004 ▶); Yang et al. (2007 ▶).

Experimental

Crystal data

[Cu2Cl4(C17H22N2)2]

M = 777.61

Monoclinic,

a = 21.070 (2) Å

b = 13.7377 (17) Å

c = 13.2449 (16) Å

β = 114.317 (2)°

V = 3493.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.55 mm−1

T = 298 K

0.20 × 0.18 × 0.10 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.746, T max = 0.860

8528 measured reflections

3077 independent reflections

1858 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.104

S = 1.06

3077 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.67 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044997/xu2644sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044997/xu2644Isup2.hkl

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

[Cu2Cl4(C17H22N2)2]	F(000) = 1608
Mr = 777.61	Dx = 1.478 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1854 reflections
a = 21.070 (2) Å	θ = 2.8–25.3°
b = 13.7377 (17) Å	µ = 1.55 mm−1
c = 13.2449 (16) Å	T = 298 K
β = 114.317 (2)°	Block, blue
V = 3493.6 (7) Å3	0.20 × 0.18 × 0.10 mm
Z = 4

Siemens SMART 1000 CCD area-detector diffractometer	3077 independent reflections
Radiation source: fine-focus sealed tube	1858 reflections with I > 2σ(I)
graphite	Rint = 0.052
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→21
Tmin = 0.746, Tmax = 0.860	k = −16→16
8528 measured reflections	l = −10→15

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0084P)2 + 19.8791P] where P = (Fo2 + 2Fc2)/3
3077 reflections	(Δ/σ)max = 0.011
199 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.67 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	0.19407 (3)	0.17462 (5)	0.40049 (6)	0.0413 (2)
Cl1	0.10161 (7)	0.26002 (11)	0.39737 (13)	0.0528 (4)
Cl2	0.23408 (8)	0.13479 (12)	0.58229 (13)	0.0534 (4)
N1	0.1603 (2)	0.1813 (3)	0.2330 (4)	0.0419 (11)
H1	0.1558	0.2458	0.2160	0.050*
N2	0.2780 (2)	0.1094 (3)	0.3951 (4)	0.0414 (12)
H2	0.3158	0.1307	0.4549	0.050*
C1	0.2153 (3)	0.1442 (4)	0.1974 (5)	0.0459 (15)
H1A	0.2050	0.0758	0.1758	0.055*
C2	0.2841 (3)	0.1484 (4)	0.2955 (5)	0.0437 (15)
H2A	0.3182	0.1108	0.2804	0.052*
H2B	0.3001	0.2154	0.3087	0.052*
C3	0.2159 (4)	0.2000 (5)	0.0982 (5)	0.071 (2)
H3A	0.1714	0.1938	0.0368	0.107*
H3B	0.2514	0.1738	0.0782	0.107*
H3C	0.2254	0.2675	0.1173	0.107*
C4	0.0901 (3)	0.1380 (4)	0.1691 (5)	0.0471 (15)
H4A	0.0782	0.1447	0.0905	0.056*
H4B	0.0557	0.1736	0.1857	0.056*
C5	0.0874 (3)	0.0315 (4)	0.1964 (5)	0.0410 (14)
C6	0.0856 (3)	−0.0402 (5)	0.1225 (5)	0.0537 (17)
H6	0.0850	−0.0230	0.0542	0.064*
C7	0.0847 (3)	−0.1367 (5)	0.1488 (7)	0.071 (2)
H7	0.0830	−0.1846	0.0981	0.085*
C8	0.0864 (3)	−0.1628 (5)	0.2511 (7)	0.070 (2)
H8	0.0869	−0.2282	0.2697	0.084*
C9	0.0873 (3)	−0.0925 (5)	0.3243 (6)	0.0627 (19)
H9	0.0877	−0.1097	0.3924	0.075*
C10	0.0877 (3)	0.0050 (5)	0.2968 (5)	0.0471 (15)
H10	0.0882	0.0528	0.3468	0.057*
C11	0.2785 (3)	0.0013 (4)	0.4004 (5)	0.0507 (16)
H11A	0.2485	−0.0240	0.3280	0.061*
H11B	0.2592	−0.0189	0.4521	0.061*
C12	0.3497 (3)	−0.0430 (4)	0.4355 (5)	0.0425 (14)
C13	0.3737 (3)	−0.0720 (4)	0.3563 (5)	0.0493 (16)
H13	0.3454	−0.0641	0.2813	0.059*
C14	0.4395 (3)	−0.1126 (4)	0.3890 (7)	0.0607 (19)
H14	0.4556	−0.1309	0.3361	0.073*
C15	0.4796 (4)	−0.1254 (5)	0.4962 (8)	0.075 (2)
H15	0.5233	−0.1537	0.5173	0.090*
C16	0.4575 (4)	−0.0976 (5)	0.5764 (6)	0.080 (2)
H16	0.4860	−0.1065	0.6511	0.096*
C17	0.3918 (3)	−0.0560 (5)	0.5438 (5)	0.0594 (18)
H17	0.3766	−0.0367	0.5974	0.071*

	U11	U22	U33	U12	U13	U23
Cu1	0.0354 (4)	0.0480 (4)	0.0427 (4)	0.0035 (3)	0.0185 (3)	−0.0051 (4)
Cl1	0.0399 (8)	0.0628 (10)	0.0571 (10)	0.0081 (7)	0.0213 (8)	−0.0107 (8)
Cl2	0.0501 (9)	0.0667 (11)	0.0458 (10)	0.0061 (8)	0.0221 (8)	0.0051 (8)
N1	0.046 (3)	0.038 (3)	0.048 (3)	0.001 (2)	0.025 (2)	0.000 (2)
N2	0.039 (3)	0.038 (3)	0.046 (3)	0.002 (2)	0.016 (2)	−0.002 (2)
C1	0.056 (4)	0.039 (4)	0.050 (4)	−0.003 (3)	0.029 (3)	−0.008 (3)
C2	0.043 (3)	0.037 (4)	0.061 (4)	0.000 (3)	0.032 (3)	−0.004 (3)
C3	0.085 (5)	0.083 (5)	0.067 (5)	0.011 (4)	0.052 (4)	0.017 (4)
C4	0.040 (3)	0.052 (4)	0.043 (4)	0.000 (3)	0.010 (3)	−0.003 (3)
C5	0.030 (3)	0.049 (4)	0.038 (4)	−0.001 (3)	0.008 (3)	−0.006 (3)
C6	0.053 (4)	0.060 (5)	0.058 (4)	−0.007 (3)	0.033 (4)	−0.009 (4)
C7	0.068 (5)	0.051 (5)	0.108 (7)	−0.008 (4)	0.052 (5)	−0.023 (4)
C8	0.059 (4)	0.051 (5)	0.107 (7)	0.000 (4)	0.042 (5)	0.009 (5)
C9	0.059 (4)	0.064 (5)	0.065 (5)	−0.004 (4)	0.026 (4)	0.012 (4)
C10	0.039 (3)	0.059 (4)	0.046 (4)	−0.010 (3)	0.020 (3)	−0.009 (3)
C11	0.047 (4)	0.040 (4)	0.070 (5)	0.002 (3)	0.029 (3)	0.004 (3)
C12	0.043 (3)	0.035 (3)	0.051 (4)	0.004 (3)	0.021 (3)	0.002 (3)
C13	0.055 (4)	0.042 (4)	0.053 (4)	0.001 (3)	0.025 (3)	−0.010 (3)
C14	0.064 (5)	0.044 (4)	0.087 (6)	0.004 (3)	0.044 (5)	−0.012 (4)
C15	0.057 (5)	0.060 (5)	0.106 (7)	0.023 (4)	0.032 (5)	0.005 (5)
C16	0.071 (5)	0.089 (6)	0.059 (5)	0.020 (4)	0.006 (4)	0.016 (4)
C17	0.066 (5)	0.069 (5)	0.044 (4)	0.012 (4)	0.024 (4)	0.004 (3)

Cu1—N1	2.034 (4)	C6—C7	1.373 (8)
Cu1—N2	2.010 (4)	C6—H6	0.9300
Cu1—Cl1	2.2598 (15)	C7—C8	1.388 (10)
Cu1—Cl2	2.2663 (17)	C7—H7	0.9300
Cu1—Cl2i	2.9858 (18)	C8—C9	1.363 (9)
N1—C4	1.493 (6)	C8—H8	0.9300
N1—C1	1.508 (6)	C9—C10	1.388 (8)
N1—H1	0.9100	C9—H9	0.9300
N2—C2	1.477 (6)	C10—H10	0.9300
N2—C11	1.487 (6)	C11—C12	1.504 (7)
N2—H2	0.9100	C11—H11A	0.9700
C1—C2	1.497 (7)	C11—H11B	0.9700
C1—C3	1.526 (8)	C12—C17	1.352 (8)
C1—H1A	0.9800	C12—C13	1.396 (7)
C2—H2A	0.9700	C13—C14	1.389 (8)
C2—H2B	0.9700	C13—H13	0.9300
C3—H3A	0.9600	C14—C15	1.331 (9)
C3—H3B	0.9600	C14—H14	0.9300
C3—H3C	0.9600	C15—C16	1.378 (10)
C4—C5	1.514 (7)	C15—H15	0.9300
C4—H4A	0.9700	C16—C17	1.393 (8)
C4—H4B	0.9700	C16—H16	0.9300
C5—C10	1.376 (7)	C17—H17	0.9300
C5—C6	1.379 (7)
N2—Cu1—N1	84.19 (18)	C5—C4—H4B	109.2
N2—Cu1—Cl1	174.43 (14)	H4A—C4—H4B	107.9
N1—Cu1—Cl1	92.59 (13)	C10—C5—C6	119.0 (6)
N2—Cu1—Cl2	89.00 (14)	C10—C5—C4	120.1 (5)
N1—Cu1—Cl2	168.46 (14)	C6—C5—C4	120.9 (5)
Cl1—Cu1—Cl2	94.90 (6)	C7—C6—C5	120.6 (6)
N2—Cu1—Cl2i	88.13 (13)	C7—C6—H6	119.7
N1—Cu1—Cl2i	88.99 (13)	C5—C6—H6	119.7
Cl1—Cu1—Cl2i	87.27 (5)	C6—C7—C8	120.0 (7)
Cl2—Cu1—Cl2i	100.11 (5)	C6—C7—H7	120.0
C4—N1—C1	113.5 (4)	C8—C7—H7	120.0
C4—N1—Cu1	114.8 (3)	C9—C8—C7	119.9 (7)
C1—N1—Cu1	110.9 (3)	C9—C8—H8	120.0
C4—N1—H1	105.6	C7—C8—H8	120.0
C1—N1—H1	105.6	C8—C9—C10	119.8 (7)
Cu1—N1—H1	105.6	C8—C9—H9	120.1
C2—N2—C11	113.8 (4)	C10—C9—H9	120.1
C2—N2—Cu1	105.7 (3)	C5—C10—C9	120.7 (6)
C11—N2—Cu1	115.6 (3)	C5—C10—H10	119.6
C2—N2—H2	107.1	C9—C10—H10	119.6
C11—N2—H2	107.1	N2—C11—C12	113.9 (4)
Cu1—N2—H2	107.1	N2—C11—H11A	108.8
C2—C1—N1	108.0 (4)	C12—C11—H11A	108.8
C2—C1—C3	112.2 (5)	N2—C11—H11B	108.8
N1—C1—C3	112.3 (5)	C12—C11—H11B	108.8
C2—C1—H1A	108.0	H11A—C11—H11B	107.7
N1—C1—H1A	108.0	C17—C12—C13	118.6 (6)
C3—C1—H1A	108.0	C17—C12—C11	121.0 (6)
N2—C2—C1	110.6 (4)	C13—C12—C11	120.4 (6)
N2—C2—H2A	109.5	C14—C13—C12	120.2 (6)
C1—C2—H2A	109.5	C14—C13—H13	119.9
N2—C2—H2B	109.5	C12—C13—H13	119.9
C1—C2—H2B	109.5	C15—C14—C13	120.0 (7)
H2A—C2—H2B	108.1	C15—C14—H14	120.0
C1—C3—H3A	109.5	C13—C14—H14	120.0
C1—C3—H3B	109.5	C14—C15—C16	121.2 (7)
H3A—C3—H3B	109.5	C14—C15—H15	119.4
C1—C3—H3C	109.5	C16—C15—H15	119.4
H3A—C3—H3C	109.5	C15—C16—C17	119.0 (7)
H3B—C3—H3C	109.5	C15—C16—H16	120.5
N1—C4—C5	112.0 (4)	C17—C16—H16	120.5
N1—C4—H4A	109.2	C12—C17—C16	121.1 (6)
C5—C4—H4A	109.2	C12—C17—H17	119.5
N1—C4—H4B	109.2	C16—C17—H17	119.5
N2—Cu1—N1—C4	125.7 (4)	N1—C4—C5—C10	72.6 (6)
Cl1—Cu1—N1—C4	−58.9 (3)	N1—C4—C5—C6	−106.4 (6)
Cl2—Cu1—N1—C4	71.6 (8)	C10—C5—C6—C7	−0.5 (9)
Cl2i—Cu1—N1—C4	−146.1 (3)	C4—C5—C6—C7	178.5 (5)
N2—Cu1—N1—C1	−4.6 (3)	C5—C6—C7—C8	−0.8 (10)
Cl1—Cu1—N1—C1	170.8 (3)	C6—C7—C8—C9	1.5 (11)
Cl2—Cu1—N1—C1	−58.7 (8)	C7—C8—C9—C10	−1.1 (10)
Cl2i—Cu1—N1—C1	83.6 (3)	C6—C5—C10—C9	0.9 (9)
N1—Cu1—N2—C2	28.3 (3)	C4—C5—C10—C9	−178.1 (5)
Cl2—Cu1—N2—C2	−161.0 (3)	C8—C9—C10—C5	−0.2 (9)
Cl2i—Cu1—N2—C2	−60.8 (3)	C2—N2—C11—C12	77.4 (6)
Cl2—Cu1—N2—C11	72.2 (4)	Cu1—N2—C11—C12	−160.0 (4)
Cl2i—Cu1—N2—C11	172.3 (4)	N2—C11—C12—C17	87.2 (7)
C4—N1—C1—C2	−151.2 (4)	N2—C11—C12—C13	−93.1 (7)
Cu1—N1—C1—C2	−20.1 (5)	C17—C12—C13—C14	−0.4 (9)
C4—N1—C1—C3	84.5 (6)	C11—C12—C13—C14	179.9 (5)
Cu1—N1—C1—C3	−144.4 (4)	C12—C13—C14—C15	1.0 (9)
C11—N2—C2—C1	79.6 (5)	C13—C14—C15—C16	−1.0 (11)
Cu1—N2—C2—C1	−48.4 (5)	C14—C15—C16—C17	0.4 (12)
N1—C1—C2—N2	45.4 (6)	C13—C12—C17—C16	−0.2 (9)
C3—C1—C2—N2	169.7 (5)	C11—C12—C17—C16	179.5 (6)
C1—N1—C4—C5	69.9 (6)	C15—C16—C17—C12	0.2 (11)
Cu1—N1—C4—C5	−59.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl1i	0.91	2.51	3.386 (5)	161

Table 1

Selected bond lengths (Å)

Cu1—N1	2.034 (4)
Cu1—N2	2.010 (4)
Cu1—Cl1	2.2598 (15)
Cu1—Cl2	2.2663 (17)
Cu1—Cl2i	2.9858 (18)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Cl1i	0.91	2.51	3.386 (5)	161

Symmetry code: (i) .