catena-Poly[[tetra-μ-formato-κ(8) O:O'-dicopper(II)]-μ-hexa-methyl-ene-tetra-mine-κ(2) N (1):N (5)].

In the title polymeric compound, [Cu2(HCO2)4(C6H12N4)] n , the Cu(II) atom is five-coordinated in a square-pyramidal geometry that is defined by four O atoms from four formate ligands and one N atom from a hexa-methyl-ene-tetra-mine ligand. The two Cu(II) atoms are separated by 2.6850 (7) Å, and together with the four formate ligands they form a paddle-wheel unit. The hexa-mine ligand uses only two of its four N atoms to link Cu2 cluster units, affording a zigzag chain running along the b-axis direction. The hexa-mine ligand lies on a mirror plane.

Related literature

For background to hexa­mine chemistry, see: Dreyfors et al. (1989 ▶); Kirillov (2011 ▶). For hexa­mine as a bridging ligand, see: Pickardt (1981 ▶); Konar et al. (2003 ▶); Wang et al. (2002 ▶). For paddle-wheel Cu2-cluster units, see: Konar et al. (2003 ▶); Chiari et al. (1988 ▶); Wu & Wang (2004 ▶); Sun et al. (2009 ▶).

Experimental

Crystal data

[Cu2(n class="CellLine">CHO2)4(C6H12N4)]

M = 447.36

Orthorhombic,

a = 13.1252 (19) Å

b = 17.281 (3) Å

c = 6.4777 (9) Å

V = 1469.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.95 mm−1

T = 103 K

0.26 × 0.24 × 0.18 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.469, T max = 0.588

5203 measured reflections

1550 independent reflections

1345 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.077

S = 1.04

1550 reflections

115 parameters

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.71 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 datablock(s) I. DOI: 10.1107/S160053681303184X/ng5345sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681303184X/ng5345Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681303184X/ng5345Isup3.mol

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

[Cu2(CHO2)4(C6H12N4)]	F(000) = 904
Mr = 447.36	Dx = 2.022 Mg m−3Dm = 2.022 Mg m−3Dm measured by not measured
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1680 reflections
a = 13.1252 (19) Å	θ = 2.4–26.4°
b = 17.281 (3) Å	µ = 2.95 mm−1
c = 6.4777 (9) Å	T = 103 K
V = 1469.3 (4) Å3	Block, green
Z = 4	0.26 × 0.24 × 0.18 mm

Bruker SMART APEX area-detector diffractometer	1550 independent reflections
Radiation source: fine-focus sealed tube	1345 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 16.0143 pixels mm-1	θmax = 26.4°, θmin = 2.4°
ω scans	h = −7→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −16→21
Tmin = 0.469, Tmax = 0.588	l = −8→8
5203 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.028	w = 1/[σ2(Fo2) + (0.0488P)2 + 0.5436P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.077	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.69 e Å−3
1550 reflections	Δρmin = −0.71 e Å−3
115 parameters

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	0.03147 (2)	0.569254 (15)	0.06885 (4)	0.01482 (13)
N1	0.09051 (15)	0.67876 (11)	0.1987 (3)	0.0167 (4)
C6	0.2292 (3)	0.7500	0.4773 (7)	0.0376 (11)
H6A	0.2607	0.7963	0.5407	0.045*	0.50
H6B	0.2607	0.7037	0.5407	0.045*	0.50
O1	−0.06061 (14)	0.61313 (10)	−0.1393 (3)	0.0243 (4)
O2	−0.11320 (13)	0.49698 (10)	−0.2546 (3)	0.0222 (4)
O3	−0.08446 (14)	0.55920 (9)	0.2587 (3)	0.0229 (4)
O4	−0.13726 (14)	0.44265 (9)	0.1462 (3)	0.0228 (4)
C1	−0.11161 (19)	0.56950 (13)	−0.2535 (4)	0.0189 (5)
H1	−0.1544	0.5944	−0.3515	0.023*
C2	−0.14152 (18)	0.50082 (13)	0.2619 (4)	0.0186 (5)
H2	−0.1938	0.5007	0.3634	0.022*
C3	0.20300 (19)	0.68165 (14)	0.1630 (4)	0.0256 (6)
H3A	0.2347	0.6346	0.2222	0.031*
H3B	0.2164	0.6817	0.0126	0.031*
C4	0.0729 (2)	0.68132 (15)	0.4251 (4)	0.0256 (6)
H4A	−0.0014	0.6813	0.4520	0.031*
H4B	0.1020	0.6342	0.4889	0.031*
C5	0.0455 (3)	0.7500	0.1069 (5)	0.0164 (7)
H5A	−0.0290	0.7500	0.1301	0.020*
H5B	0.0576	0.7500	−0.0440	0.020*
N2	0.2502 (3)	0.7500	0.2553 (6)	0.0306 (8)
N3	0.1187 (3)	0.7500	0.5219 (5)	0.0299 (8)

	U11	U22	U33	U12	U13	U23
Cu1	0.01667 (19)	0.01185 (19)	0.01595 (19)	−0.00041 (10)	−0.00034 (10)	−0.00042 (10)
N1	0.0205 (10)	0.0106 (9)	0.0191 (10)	0.0003 (8)	−0.0004 (8)	0.0002 (8)
C6	0.047 (3)	0.0180 (19)	0.048 (3)	0.000	−0.028 (2)	0.000
O1	0.0307 (10)	0.0168 (9)	0.0253 (9)	0.0018 (7)	−0.0092 (8)	0.0001 (7)
O2	0.0245 (9)	0.0181 (9)	0.0240 (9)	0.0009 (7)	−0.0066 (7)	0.0015 (7)
O3	0.0232 (10)	0.0207 (9)	0.0248 (10)	−0.0027 (7)	0.0062 (7)	−0.0043 (7)
O4	0.0253 (9)	0.0197 (9)	0.0234 (9)	−0.0044 (7)	0.0056 (8)	−0.0033 (7)
C1	0.0182 (12)	0.0205 (12)	0.0181 (13)	0.0038 (9)	0.0019 (9)	0.0032 (9)
C2	0.0171 (12)	0.0195 (12)	0.0192 (12)	0.0037 (10)	−0.0002 (9)	0.0018 (9)
C3	0.0215 (13)	0.0151 (12)	0.0401 (16)	0.0018 (10)	−0.0030 (11)	−0.0002 (11)
C4	0.0407 (16)	0.0161 (13)	0.0199 (13)	−0.0014 (12)	−0.0026 (11)	0.0029 (9)
C5	0.0196 (17)	0.0127 (16)	0.0169 (16)	0.000	−0.0021 (13)	0.000
N2	0.0226 (16)	0.0167 (15)	0.052 (2)	0.000	−0.0107 (14)	0.000
N3	0.053 (2)	0.0145 (15)	0.0219 (16)	0.000	−0.0136 (15)	0.000

Cu1—O1	1.9632 (17)	O2—Cu1i	1.9769 (16)
Cu1—O3	1.9640 (18)	O3—C2	1.257 (3)
Cu1—O2i	1.9769 (17)	O4—C2	1.255 (3)
Cu1—O4i	1.9777 (18)	C2—H2	0.950
Cu1—N1	2.2112 (19)	O4—Cu1i	1.9777 (18)
Cu1—Cu1i	2.6848 (6)	C3—N2	1.461 (3)
N1—C4	1.485 (3)	C3—H3A	0.990
N1—C5	1.489 (3)	C3—H3B	0.990
N1—C3	1.495 (3)	C4—N3	1.471 (3)
C6—N2	1.464 (6)	C4—H4A	0.991
C6—N3	1.479 (6)	C4—H4B	0.990
C6—H6A	0.990	C5—N1ii	1.489 (3)
C6—H6B	0.990	C5—H5A	0.989
O1—C1	1.251 (3)	C5—H5B	0.990
O2—C1	1.253 (3)	N2—C3ii	1.461 (3)
C1—H1	0.951	N3—C4ii	1.471 (3)
O1—Cu1—O3	89.26 (8)	H5B—C5—N1	109.30
O1—Cu1—O2i	167.34 (7)	C4—N1—Cu1	110.27 (15)
H1—C1—O1	116.00	H4A—C4—N3	109.13
H1—C1—O2	116.04	H4B—C4—N3	109.16
O3—Cu1—O2i	89.33 (7)	C5—N1—Cu1	114.62 (15)
O1—Cu1—O4i	89.34 (8)	C3—N1—Cu1	108.41 (14)
O3—Cu1—O4i	167.36 (7)	N2—C6—N3	112.1 (3)
O2i—Cu1—O4i	89.28 (8)	C1—O1—Cu1	120.20 (15)
H2—C2—O3	116.33	C1—O2—Cu1i	124.51 (16)
H2—C2—O4	116.33	C2—O3—Cu1	122.90 (15)
O1—Cu1—N1	98.43 (7)	C2—O4—Cu1i	122.36 (16)
O3—Cu1—N1	96.26 (7)	H3A—C3—H3B	107.88
O2i—Cu1—N1	94.24 (7)	H4A—C4—H4B	107.83
O4i—Cu1—N1	96.37 (7)	H5B—C5—H5A	107.97
O1—Cu1—Cu1i	85.79 (5)	O1—C1—O2	127.9 (2)
O3—Cu1—Cu1i	83.73 (5)	O4—C2—O3	127.3 (2)
O2i—Cu1—Cu1i	81.54 (5)	N2—C3—N1	112.5 (2)
O4i—Cu1—Cu1i	83.64 (5)	N3—C4—N1	112.4 (2)
N1—Cu1—Cu1i	175.78 (5)	N1—C5—N1ii	111.5 (3)
H3A—C3—N1	109.11	C3—N2—C3ii	107.9 (3)
H3B—C3—N1	109.13	C3—N2—C6	108.8 (2)
H3A—C3—N2	109.08	H6A—C6—N2	109.20
H4B—C4—N3	109.06	H6B—C6—N2	109.20
C4—N1—C5	107.9 (2)	H6A—C6—N3	109.18
C4—N1—C3	107.8 (2)	H6B—C6—N3	109.18
H4A—C4—N1	109.08	C3ii—N2—C6	108.8 (2)
H4B—C4—N1	109.13	C4ii—N3—C4	107.6 (3)
C5—N1—C3	107.6 (2)	C4ii—N3—C6	108.5 (2)
H5A—C5—N1	109.35	C4—N3—C6	108.5 (2)