Bis(hexa-methyl-enetetra-mine)bis-(tri-chloro-acetato)copper(II).

In the title compound, [Cu(C(2)Cl(3)O(2))(2)(C(6)H(12)N(4))(2)], the Cu(II) ion (site symmetry 2) is coordinated by two trichloro-acetate anions and two hexa-methyl-enetetra-mine mol-ecules, resulting in a distorted CuN(2)O(2) geometry that is inter-mediate between tetra-hedral and square planar. The Cl atoms are disordered over two sets of sites, with relative occupancies of 0.749 (7) and 0.251 (7). In the crystal, the packing is consolidated by inter-molecular C-H⋯O inter-actions.

Related literature

For background to coordination networks, see: Chen et al. (2001 ▶). For a related structure, see: Moncol et al. (2007 ▶).

Experimental

Crystal data

[Cu(C2Cl3O2)2(C6H12N4)2]

M = 668.67

Monoclinic,

a = 23.291 (5) Å

b = 6.4759 (13) Å

c = 20.702 (4) Å

β = 121.36 (3)°

V = 2666.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.46 mm−1

T = 293 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

12444 measured reflections

3048 independent reflections

2740 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.184

S = 1.09

3048 reflections

187 parameters

78 restraints

H-atom parameters constrained

Δρmax = 1.52 e Å−3

Δρmin = −0.98 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043736/hb5145sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043736/hb5145Isup2.hkl

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

[Cu(C2Cl3O2)2(C6H12N4)2]	F(000) = 1356
Mr = 668.67	Dx = 1.666 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.291 (5) Å	Cell parameters from 2740 reflections
b = 6.4759 (13) Å	θ = 3.3–27.5°
c = 20.702 (4) Å	µ = 1.46 mm−1
β = 121.36 (3)°	T = 293 K
V = 2666.3 (9) Å3	Block, green
Z = 4	0.30 × 0.20 × 0.15 mm

Bruker SMART CCD diffractometer	2740 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 27.5°, θmin = 3.3°
Detector resolution: 3 pixels mm-1	h = −30→30
ω scans	k = −7→8
12444 measured reflections	l = −26→26
3048 independent reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.1275P)2 + 3.9764P] where P = (Fo2 + 2Fc2)/3
3048 reflections	(Δ/σ)max = 0.042
187 parameters	Δρmax = 1.52 e Å−3
78 restraints	Δρmin = −0.98 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)
Cu1	0.0000	0.79415 (8)	0.2500	0.0315 (2)
O1	0.06660 (12)	0.7420 (4)	0.35558 (14)	0.0428 (6)
O2	0.01619 (16)	0.4397 (5)	0.33908 (17)	0.0669 (9)
N1	0.07476 (12)	0.8907 (4)	0.23307 (14)	0.0303 (5)
N2	0.15738 (18)	1.1697 (5)	0.2701 (2)	0.0483 (7)
N3	0.10588 (16)	1.0194 (5)	0.14402 (17)	0.0445 (7)
N4	0.18698 (16)	0.8189 (5)	0.2547 (2)	0.0477 (8)
C1	0.10233 (18)	1.0882 (5)	0.27694 (19)	0.0396 (7)
H1A	0.0667	1.1900	0.2584	0.047*
H1B	0.1183	1.0629	0.3299	0.047*
C2	0.1318 (2)	1.2073 (6)	0.1894 (3)	0.0499 (9)
H2A	0.0962	1.3096	0.1704	0.060*
H2B	0.1678	1.2629	0.1840	0.060*
C3	0.1605 (2)	0.8664 (7)	0.1743 (2)	0.0519 (9)
H3A	0.1967	0.9186	0.1687	0.062*
H3B	0.1439	0.7402	0.1449	0.062*
C4	0.13189 (18)	0.7387 (5)	0.2620 (2)	0.0406 (7)
H4A	0.1485	0.7085	0.3147	0.049*
H4B	0.1156	0.6108	0.2337	0.049*
C5	0.21037 (19)	1.0132 (7)	0.2968 (2)	0.0547 (10)
H5A	0.2277	0.9861	0.3500	0.066*
H5B	0.2470	1.0670	0.2924	0.066*
C6	0.05198 (17)	0.9380 (6)	0.15232 (18)	0.0410 (7)
H6A	0.0346	0.8129	0.1225	0.049*
H6B	0.0157	1.0379	0.1328	0.049*
C7	0.1155 (2)	0.5072 (6)	0.45812 (19)	0.0579 (10)
C8	0.05989 (16)	0.5630 (6)	0.37587 (17)	0.0378 (7)
Cl1	0.1084 (2)	0.6786 (5)	0.51998 (15)	0.0872 (9)	0.749 (7)
Cl2	0.1139 (3)	0.2478 (4)	0.48019 (19)	0.1149 (15)	0.749 (7)
Cl3	0.19694 (13)	0.5452 (9)	0.47005 (18)	0.1191 (16)	0.749 (7)
Cl1'	0.1398 (7)	0.7198 (12)	0.5194 (5)	0.102 (2)	0.251 (7)
Cl2'	0.0839 (6)	0.2990 (15)	0.4873 (5)	0.106 (2)	0.251 (7)
Cl3'	0.1851 (4)	0.430 (2)	0.4518 (6)	0.133 (3)	0.251 (7)

	U11	U22	U33	U12	U13	U23
Cu1	0.0256 (3)	0.0403 (4)	0.0277 (3)	0.000	0.0133 (2)	0.000
O1	0.0349 (12)	0.0555 (14)	0.0316 (12)	−0.0009 (10)	0.0129 (10)	0.0104 (10)
O2	0.0620 (18)	0.0575 (17)	0.0507 (16)	−0.0134 (14)	0.0079 (14)	0.0011 (14)
N1	0.0288 (11)	0.0309 (12)	0.0326 (12)	0.0013 (9)	0.0170 (10)	0.0000 (10)
N2	0.0535 (19)	0.0428 (15)	0.0538 (18)	−0.0155 (14)	0.0316 (16)	−0.0081 (14)
N3	0.0491 (17)	0.0516 (17)	0.0424 (15)	−0.0001 (13)	0.0304 (13)	0.0039 (13)
N4	0.0360 (15)	0.0541 (18)	0.061 (2)	0.0086 (12)	0.0305 (15)	0.0094 (15)
C1	0.0476 (18)	0.0345 (15)	0.0432 (17)	−0.0034 (13)	0.0282 (15)	−0.0068 (14)
C2	0.059 (2)	0.0409 (19)	0.058 (2)	−0.0043 (15)	0.037 (2)	0.0067 (16)
C3	0.059 (2)	0.056 (2)	0.061 (2)	0.0055 (19)	0.046 (2)	0.0001 (19)
C4	0.0395 (17)	0.0361 (15)	0.054 (2)	0.0087 (13)	0.0295 (16)	0.0081 (15)
C5	0.0361 (18)	0.071 (3)	0.053 (2)	−0.0117 (17)	0.0208 (16)	0.0022 (19)
C6	0.0376 (16)	0.0516 (19)	0.0336 (15)	−0.0027 (14)	0.0185 (13)	−0.0008 (14)
C7	0.064 (2)	0.058 (2)	0.0289 (16)	0.0017 (19)	0.0086 (16)	0.0075 (16)
C8	0.0346 (15)	0.0496 (18)	0.0253 (13)	0.0018 (13)	0.0129 (12)	0.0010 (13)
Cl1	0.115 (2)	0.0970 (16)	0.0377 (8)	0.0104 (14)	0.0319 (13)	−0.0064 (9)
Cl2	0.147 (3)	0.0608 (12)	0.0681 (13)	0.0104 (14)	0.0082 (17)	0.0246 (11)
Cl3	0.0462 (11)	0.208 (5)	0.0721 (16)	0.0175 (17)	0.0089 (11)	0.030 (2)
Cl1'	0.131 (5)	0.090 (3)	0.036 (2)	0.008 (3)	0.010 (3)	−0.011 (2)
Cl2'	0.148 (5)	0.064 (3)	0.063 (3)	−0.009 (3)	0.024 (3)	0.026 (3)
Cl3'	0.053 (3)	0.196 (6)	0.092 (4)	0.044 (4)	−0.001 (3)	0.005 (4)

Cu1—O1	1.941 (3)	C1—H1B	0.9700
Cu1—O1i	1.941 (3)	C2—H2A	0.9700
Cu1—N1i	2.045 (2)	C2—H2B	0.9700
Cu1—N1	2.045 (2)	C3—H3A	0.9700
O1—C8	1.270 (4)	C3—H3B	0.9700
O2—C8	1.203 (5)	C4—H4A	0.9700
N1—C6	1.499 (4)	C4—H4B	0.9700
N1—C4	1.506 (4)	C5—H5A	0.9700
N1—C1	1.505 (4)	C5—H5B	0.9700
N2—C1	1.460 (5)	C6—H6A	0.9700
N2—C5	1.465 (6)	C6—H6B	0.9700
N2—C2	1.473 (6)	C7—C8	1.553 (5)
N3—C6	1.452 (4)	C7—Cl2	1.747 (5)
N3—C2	1.462 (5)	C7—Cl1'	1.754 (7)
N3—C3	1.470 (5)	C7—Cl3'	1.764 (7)
N4—C4	1.463 (5)	C7—Cl1	1.766 (5)
N4—C5	1.465 (6)	C7—Cl2'	1.786 (7)
N4—C3	1.477 (5)	C7—Cl3	1.797 (5)
C1—H1A	0.9700
O1—Cu1—O1i	159.95 (17)	N4—C4—H4A	109.3
O1—Cu1—N1i	96.49 (11)	N1—C4—H4A	109.3
O1i—Cu1—N1i	89.63 (10)	N4—C4—H4B	109.3
O1—Cu1—N1	89.63 (10)	N1—C4—H4B	109.3
O1i—Cu1—N1	96.49 (11)	H4A—C4—H4B	108.0
N1i—Cu1—N1	144.38 (14)	N2—C5—N4	112.9 (3)
C8—O1—Cu1	111.6 (2)	N2—C5—H5A	109.0
C6—N1—C4	107.7 (2)	N4—C5—H5A	109.0
C6—N1—C1	107.0 (3)	N2—C5—H5B	109.0
C4—N1—C1	107.7 (3)	N4—C5—H5B	109.0
C6—N1—Cu1	114.51 (19)	H5A—C5—H5B	107.8
C4—N1—Cu1	112.75 (19)	N3—C6—N1	112.3 (3)
C1—N1—Cu1	106.88 (18)	N3—C6—H6A	109.1
C1—N2—C5	108.8 (3)	N1—C6—H6A	109.1
C1—N2—C2	108.3 (3)	N3—C6—H6B	109.1
C5—N2—C2	107.9 (3)	N1—C6—H6B	109.1
C6—N3—C2	108.7 (3)	H6A—C6—H6B	107.9
C6—N3—C3	108.3 (3)	C8—C7—Cl2	113.0 (3)
C2—N3—C3	108.1 (3)	C8—C7—Cl1'	112.4 (4)
C4—N4—C5	108.6 (3)	Cl2—C7—Cl1'	127.5 (4)
C4—N4—C3	108.4 (3)	C8—C7—Cl3'	105.0 (4)
C5—N4—C3	107.5 (3)	Cl2—C7—Cl3'	83.9 (5)
N2—C1—N1	111.6 (3)	Cl1'—C7—Cl3'	108.3 (5)
N2—C1—H1A	109.3	C8—C7—Cl1	108.0 (3)
N1—C1—H1A	109.3	Cl2—C7—Cl1	113.0 (3)
N2—C1—H1B	109.3	Cl1'—C7—Cl1	25.7 (4)
N1—C1—H1B	109.3	Cl3'—C7—Cl1	131.9 (4)
H1A—C1—H1B	108.0	C8—C7—Cl2'	106.9 (4)
N3—C2—N2	112.3 (3)	Cl2—C7—Cl2'	27.9 (4)
N3—C2—H2A	109.2	Cl1'—C7—Cl2'	112.5 (5)
N2—C2—H2A	109.2	Cl3'—C7—Cl2'	111.6 (5)
N3—C2—H2B	109.2	Cl1—C7—Cl2'	91.0 (4)
N2—C2—H2B	109.2	C8—C7—Cl3	109.7 (3)
H2A—C2—H2B	107.9	Cl2—C7—Cl3	105.1 (3)
N3—C3—N4	112.4 (3)	Cl1'—C7—Cl3	82.7 (5)
N3—C3—H3A	109.1	Cl3'—C7—Cl3	26.5 (4)
N4—C3—H3A	109.1	Cl1—C7—Cl3	107.8 (3)
N3—C3—H3B	109.1	Cl2'—C7—Cl3	130.4 (5)
N4—C3—H3B	109.1	O2—C8—O1	127.3 (3)
H3A—C3—H3B	107.8	O2—C8—C7	119.2 (3)
N4—C4—N1	111.6 (3)	O1—C8—C7	113.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2ii	0.97	2.52	3.416 (5)	153

Cu1—O1	1.941 (3)
Cu1—N1	2.045 (2)

O1—Cu1—O1i	159.95 (17)
O1—Cu1—N1	89.63 (10)
O1i—Cu1—N1	96.49 (11)
N1i—Cu1—N1	144.38 (14)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2ii	0.97	2.52	3.416 (5)	153

Symmetry code: (ii) .