catena-Poly[[[aqua­(propane-1,3-diamine-κ2N,N′)copper(II)]-μ-fumarato-κ2O:O′] monohydrate]

Padmanabhan, M.; Joseph, J.C.; Olsson, S.; Bakir, M.

doi:10.1107/S1600536808000160

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Pages m303-m304

doi:10.1107/S1600536808000160

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catena-Poly[[[aqua(propane-1,3-diamine-κ²N,N′)copper(II)]-μ-fumarato-κ²O:O′] monohydrate]

M. Padmanabhan,^a James C. Joseph,^a Susanne Olsson ^b and Mohammed Bakir ^c ^*

^aSchool of Chemical Sciences, Mahatma Gandhi University, Kottayam 686 560, Kerala, India, ^bDepartment of Chemistry, Göteborg University, SE-41296 Göteborg, Sweden, and ^cDepartment of Chemistry, The University of the West Indies – Mona Campus, Kingston 7, Jamaica
^*Correspondence e-mail: mohammed.bakir@uwimona.edu.jm

(Received 13 December 2007; accepted 2 January 2008; online 9 January 2008)

The asymmetric unit of the title compound, {[Cu(C₄H₂O₄)(C₃H₁₀N₂)(H₂O)]·H₂O}_n, consists of two Cu^II atoms, half each of two propane-1,3-diamine ligands and two coordinated water molecules, all lying on crystallographic mirror planes, also one fumarate dianion and one uncoordinated water molecule in a general position. The Cu(C₃H₁₀N₂)(H₂O) units are linked via fumarate dianions into a zigzag chain running along the a axis. A longer Cu—O distance [2.873 (3) Å] is to a water molecule bridging equivalent Cu^II atoms in adjacent chains, forming a three-dimensional framework. One of the Cu^II atoms is in a distorted square-pyramidal environment and the other is in a pseudo-octahedral geometry of the [5+1] type. O—H⋯O and N—H⋯O hydrogen bonds are observed in the crystal structure.

Related literature

For related literature, see: Chan (2007 ); Dong et al. (2006 ); Mori et al. (2005 ); Mukherjee et al. (2004 ); Rudkevich (2007 ); Shi et al. (2007 ); Ye et al. (2005 ); Zheng & Xie (2004 ).

Experimental

Crystal data

[Cu(C₄H₂O₄)(C₃H₁₀N₂)(H₂O)]·H₂O
M_r = 286.76
Orthorhombic, P m c 2₁
a = 14.993 (3) Å
b = 8.0948 (17) Å
c = 9.259 (2) Å
V = 1123.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.96 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Rigaku R-AXIS IIC image-plate system diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 ) T_min = 0.543, T_max = 0.82
10226 measured reflections
3345 independent reflections
2913 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.096
S = 1.14
3345 reflections
154 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.82 e Å⁻³
Absolute structure: Flack (1983 ), with 1415 Friedel pairs
Flack parameter: 0.011 (18)

Table 1
Selected geometric parameters (Å, °)

Cu1—N1	2.019 (3)
Cu1—O1	2.024 (2)
Cu1—O3	2.180 (3)
Cu2—N1′	2.010 (3)
Cu2—O1′	2.015 (3)
Cu2—O3′	2.270 (3)

N1ⁱ—Cu1—N1	90.42 (18)
N1—Cu1—O1	88.93 (11)
N1—Cu1—O1ⁱ	173.62 (11)
O1—Cu1—O1ⁱ	91.00 (14)
N1—Cu1—O3	97.70 (11)
O1—Cu1—O3	88.68 (10)
N1′ⁱⁱ—Cu2—N1′	89.83 (19)
N1′—Cu2—O1′	89.47 (10)
N1′—Cu2—O1′ⁱⁱ	175.68 (13)
O1′—Cu2—O1′ⁱⁱ	90.90 (15)
N1′—Cu2—O3′	95.62 (11)
O1′—Cu2—O3′	88.69 (10)
Symmetry codes: (i) -x+1, y, z; (ii) -x, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O2′	0.87	2.17	2.887 (5)	140
O3—H3⋯O2ⁱⁱⁱ	0.85	1.88	2.713 (3)	166
O3′—H3′⋯O2′^iv	0.85	1.91	2.708 (3)	156
N1—H1A⋯O1^v	0.90	2.20	3.083 (4)	167
N1′—H1′A⋯O4^vi	0.90	2.25	3.071 (5)	151
N1′—H1′B⋯O1′^vii	0.90	2.26	3.135 (3)	164
O4—H4B⋯O2^viii	0.86	1.99	2.785 (4)	153
Symmetry codes: (iii) $[-x+1, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[-x, -y, z+{\script{1\over 2}}]$ ; (v) $[x, -y+1, z+{\script{1\over 2}}]$ ; (vi) $[x, -y, z+{\script{1\over 2}}]$ ; (vii) $[x, -y, z-{\script{1\over 2}}]$ ; (viii) x, y, z-1.

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000160/ci2545sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808000160/ci2545Isup2.hkl

checkCIF report

Comment top

Metallo-polymers are of current interest because of their physical properties and applications in many areas (Chan, 2007; Rudkevich, 2007; Shi et al., 2007; Mori et al., 2005). The synthesis and crystal structure of copper-polycarboxylate polymers have been reported (Mukherjee et al., 2004; Ye et al., 2005). Now we report here the crystal structure of the title compound.

The asymmetric unit of the title compound consists of two Cu^II atoms, one half each of two 1,3-diaminopropane ligands and two water molecules, all lying on crystallographic mirror planes, and one fumarate dianion. As shown in Fig.1, the [(aqua)(propane-1,3-diamino-κ²-N,N)copper(II)] units are linked via amphi-monodentate fumarate dianions into a zigzag chain along the a axis. Each Cu^II atom has a distorted square-pyramidal environment, being coordinated by two N atoms of the 1,3-diaminopropane ligand and two cis-oxygen atoms from two bridging fumarate dianions in the basal positions and a water molecule in the apical position. The axial Cu—O bond distance [2.180 (3) Å] is shorter, and the Cu···Cu distance [9.084 Å] is longer than the corresponding distances [2.481 Å and 8.857 Å] reported for fumarate bridged [(aqua)(1,2-dimethylethane-1,2-diamine-κ²-N,N)copper(II)] (Mukherjee et al., 2004). The six-membered metallocyclic ring formed by the N,N-bidentae propane-1,3-diamine ligand and the Cu^II atom adopts a chair conformation.

In the crystal structure, the longer Cu2—O3'(-x,-y,-1/2 + z) coordination [2.873 (3) Å] involving the water molecule bridges Cu^II atoms of adjacent zigzag chains, leading to the formation a three-dimensional framework. The coordination of the Cu2 atom in the network is pseudo-octahedral of the [5 + 1] type. The structure is further stabilized by O—H···O and N—H···O hydrogen bonds (Table 2). The geometry of hydrogen bonds are similar to those reported for a variety of copper compounds (Zheng & Xie, 2004; Dong et al., 2006).

Due to their convenient synthesis and potential catalytic and sorption applications, studies are in progress in our laboratories to synthesis several other polycarboxylate metallopolymers which are structurally and electronically tuned by polyamines.

Related literature top

For related literature, see: Chan (2007); Dong et al. (2006); Mori et al. (2005); Mukherjee et al. (2004); Rudkevich (2007); Shi et al. (2007); Ye et al. (2005); Zheng & Xie (2004).

Experimental top

Fumaric acid (0.12 g, 1.0 mmol) was added to an aqueous suspension of CuCO₃.Cu(OH)₂.H₂O (0.12 g, 0.50 mmol), and then propane-1,3-diamine (0.08 ml, 1.0 mmol) was added dropwise, with stirring and heating. The mixture was allowed to react for 2 h and filtered, and the filtrate was allowed to stand at room temperature for 4 d. At the end of this time, deep blue colourless crystals deposited, which were filtered off and dried in air.

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear (Rigaku, 2000); data reduction: CrystalClear (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The coordination environment of the Cu^II center, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [symmetry code: -x + 1, y, z.]
	Fig. 2. Part of a zigzag polymeric chain of the title compound. Hydrogen bonds are shown as dashed lines.

catena-Poly[[[aqua(propane-1,3-diamine-κ²N,N')copper(II)]-µ- fumarato-κ²O:O'] monohydrate] top

Crystal data top

[Cu(C₄H₂O₄)(C₃H₁₀N₂)(H₂O)]·H₂O	F(000) = 596
M_r = 286.76	D_x = 1.701 Mg m⁻³
Orthorhombic, Pmc2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2	Cell parameters from 6311 reflections
a = 14.993 (3) Å	θ = 1.4–25.0°
b = 8.0948 (17) Å	µ = 1.96 mm⁻¹
c = 9.259 (2) Å	T = 293 K
V = 1123.7 (4) Å³	Plate, blue
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Rigaku R-AXIS IIC image-plate system diffractometer	3345 independent reflections
Radiation source: fine-focus sealed tube	2913 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 105 pixels mm^-1	θ_max = 33.0°, θ_min = 1.4°
ϕ scans	h = −20→20
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	k = −11→11
T_min = 0.543, T_max = 0.82	l = −12→11
10226 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.044P)²] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max = 0.001
3345 reflections	Δρ_max = 0.47 e Å⁻³
154 parameters	Δρ_min = −0.82 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1415 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.011 (18)

Crystal data top

[Cu(C₄H₂O₄)(C₃H₁₀N₂)(H₂O)]·H₂O	V = 1123.7 (4) Å³
M_r = 286.76	Z = 4
Orthorhombic, Pmc2₁	Mo Kα radiation
a = 14.993 (3) Å	µ = 1.96 mm⁻¹
b = 8.0948 (17) Å	T = 293 K
c = 9.259 (2) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Rigaku R-AXIS IIC image-plate system diffractometer	3345 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	2913 reflections with I > 2σ(I)
T_min = 0.543, T_max = 0.82	R_int = 0.054
10226 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.096	Δρ_max = 0.47 e Å⁻³
S = 1.14	Δρ_min = −0.82 e Å⁻³
3345 reflections	Absolute structure: Flack (1983), 1415 Friedel pairs
154 parameters	Absolute structure parameter: 0.011 (18)
1 restraint

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.5000	0.54986 (6)	0.72824 (5)	0.02037 (11)
Cu2	0.0000	−0.01107 (9)	0.46996 (5)	0.02080 (12)
O1	0.40374 (16)	0.3988 (3)	0.6507 (2)	0.0289 (5)
O1'	0.09578 (17)	0.1419 (3)	0.5436 (3)	0.0286 (5)
O2	0.34823 (19)	0.3174 (4)	0.8619 (3)	0.0505 (8)
O2'	0.1459 (2)	0.2442 (4)	0.3340 (3)	0.0484 (8)
O3	0.5000	0.6785 (5)	0.5214 (4)	0.0381 (9)
H3	0.5511	0.6699	0.4823	0.057*
O3'	0.0000	−0.1382 (5)	0.6885 (3)	0.0342 (8)
H3'	−0.0533	−0.1602	0.7130	0.051*
N1	0.4044 (2)	0.6854 (4)	0.8260 (3)	0.0299 (6)
H1A	0.3986	0.6477	0.9170	0.036*
H1B	0.3525	0.6652	0.7804	0.036*
N1'	0.0947 (2)	−0.1553 (4)	0.3820 (3)	0.0279 (6)
H1'A	0.1472	−0.1269	0.4218	0.034*
H1'B	0.0979	−0.1306	0.2874	0.034*
C1	0.4162 (3)	0.8666 (5)	0.8328 (5)	0.0461 (10)
H1C	0.3653	0.9154	0.8814	0.055*
H1D	0.4184	0.9108	0.7355	0.055*
C1'	0.0848 (3)	−0.3360 (4)	0.3952 (4)	0.0359 (8)
H1'C	0.0838	−0.3662	0.4965	0.043*
H1'D	0.1357	−0.3898	0.3507	0.043*
C2	0.5000	0.9135 (7)	0.9117 (7)	0.0498 (14)
H2A	0.5000	0.8602	1.0056	0.060*
H2B	0.5000	1.0320	0.9276	0.060*
C2'	0.0000	−0.3955 (6)	0.3235 (6)	0.0402 (12)
H2'A	0.0000	−0.5153	0.3231	0.048*
H2'B	0.0000	−0.3588	0.2238	0.048*
C3	0.34705 (18)	0.3246 (4)	0.7272 (4)	0.0272 (5)
C3'	0.1494 (2)	0.2248 (4)	0.4675 (4)	0.0264 (6)
C4	0.2697 (2)	0.2419 (4)	0.6537 (3)	0.0275 (6)
H4	0.2515	0.1388	0.6869	0.033*
C4'	0.2259 (2)	0.3090 (4)	0.5432 (3)	0.0261 (6)
H4'	0.2434	0.4129	0.5112	0.031*
O4	0.2556 (3)	0.1667 (5)	0.0869 (5)	0.0787 (12)
H4A	0.2359	0.2358	0.1510	0.118*
H4B	0.2686	0.2327	0.0168	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0162 (2)	0.0256 (3)	0.0193 (2)	0.000	0.000	−0.0011 (2)
Cu2	0.0144 (2)	0.0250 (3)	0.0230 (2)	0.000	0.000	−0.00166 (16)
O1	0.0209 (12)	0.0378 (13)	0.0279 (12)	−0.0114 (9)	0.0002 (8)	−0.0035 (9)
O1'	0.0187 (13)	0.0361 (13)	0.0309 (12)	−0.0071 (10)	0.0010 (9)	−0.0060 (10)
O2	0.0413 (17)	0.085 (2)	0.0248 (12)	−0.0221 (15)	−0.0051 (11)	0.0059 (13)
O2'	0.0428 (16)	0.076 (2)	0.0268 (12)	−0.0199 (15)	−0.0077 (11)	0.0016 (11)
O3	0.0268 (19)	0.059 (2)	0.0288 (17)	0.000	0.000	0.0176 (15)
O3'	0.0233 (17)	0.052 (2)	0.0278 (17)	0.000	0.000	0.0130 (12)
N1	0.0258 (16)	0.0330 (16)	0.0309 (14)	0.0067 (11)	0.0060 (11)	−0.0027 (10)
N1'	0.0240 (16)	0.0295 (16)	0.0303 (15)	0.0048 (12)	0.0025 (11)	0.0001 (11)
C1	0.046 (2)	0.030 (2)	0.062 (3)	0.0113 (16)	0.0114 (19)	0.0031 (16)
C1'	0.0327 (18)	0.0295 (18)	0.045 (2)	0.0088 (14)	0.0022 (14)	0.0057 (14)
C2	0.059 (4)	0.030 (3)	0.059 (4)	0.000	0.000	−0.010 (2)
C2'	0.047 (3)	0.024 (3)	0.050 (3)	0.000	0.000	−0.007 (2)
C3	0.0199 (13)	0.0347 (15)	0.0270 (13)	−0.0054 (9)	−0.0014 (15)	0.0028 (16)
C3'	0.0155 (14)	0.0348 (16)	0.0289 (14)	−0.0039 (11)	−0.0022 (12)	−0.0027 (12)
C4	0.0219 (16)	0.0346 (17)	0.0260 (15)	−0.0089 (12)	0.0026 (11)	−0.0019 (11)
C4'	0.0194 (15)	0.0294 (16)	0.0296 (15)	−0.0046 (12)	−0.0011 (11)	−0.0036 (11)
O4	0.063 (2)	0.099 (3)	0.074 (2)	−0.004 (2)	0.0086 (16)	0.037 (2)

Geometric parameters (Å, º) top

Cu1—N1ⁱ	2.019 (3)	N1'—H1'B	0.90
Cu1—N1	2.019 (3)	C1—C2	1.502 (6)
Cu1—O1	2.024 (2)	C1—H1C	0.97
Cu1—O1ⁱ	2.024 (2)	C1—H1D	0.97
Cu1—O3	2.180 (3)	C1'—C2'	1.513 (5)
Cu2—N1'ⁱⁱ	2.010 (3)	C1'—H1'C	0.97
Cu2—N1'	2.010 (3)	C1'—H1'D	0.97
Cu2—O1'	2.015 (3)	C2—C1ⁱ	1.502 (6)
Cu2—O1'ⁱⁱ	2.015 (3)	C2—H2A	0.97
Cu2—O3'	2.270 (3)	C2—H2B	0.97
O1—C3	1.259 (4)	C2'—C1'ⁱⁱ	1.513 (5)
O1'—C3'	1.262 (4)	C2'—H2'A	0.97
O2—C3	1.249 (5)	C2'—H2'B	0.97
O2'—C3'	1.247 (4)	C3—C4	1.502 (4)
O3—H3	0.85	C3'—C4'	1.507 (4)
O3'—H3'	0.85	C4—C4'	1.331 (4)
N1—C1	1.479 (5)	C4—H4	0.93
N1—H1A	0.90	C4'—H4'	0.93
N1—H1B	0.90	O4—H4A	0.86
N1'—C1'	1.475 (5)	O4—H4B	0.86
N1'—H1'A	0.90

N1ⁱ—Cu1—N1	90.42 (18)	N1—C1—H1C	109.3
N1ⁱ—Cu1—O1	173.62 (11)	C2—C1—H1C	109.3
N1—Cu1—O1	88.93 (11)	N1—C1—H1D	109.3
N1ⁱ—Cu1—O1ⁱ	88.93 (11)	C2—C1—H1D	109.3
N1—Cu1—O1ⁱ	173.62 (11)	H1C—C1—H1D	107.9
O1—Cu1—O1ⁱ	91.00 (14)	N1'—C1'—C2'	111.3 (3)
N1ⁱ—Cu1—O3	97.70 (12)	N1'—C1'—H1'C	109.4
N1—Cu1—O3	97.70 (11)	C2'—C1'—H1'C	109.4
O1—Cu1—O3	88.68 (10)	N1'—C1'—H1'D	109.4
O1ⁱ—Cu1—O3	88.68 (10)	C2'—C1'—H1'D	109.4
N1'ⁱⁱ—Cu2—N1'	89.83 (19)	H1'C—C1'—H1'D	108.0
N1'ⁱⁱ—Cu2—O1'	175.68 (13)	C1—C2—C1ⁱ	113.6 (5)
N1'—Cu2—O1'	89.47 (10)	C1—C2—H2A	108.9
N1'ⁱⁱ—Cu2—O1'ⁱⁱ	89.47 (10)	C1ⁱ—C2—H2A	108.9
N1'—Cu2—O1'ⁱⁱ	175.68 (13)	C1—C2—H2B	108.9
O1'—Cu2—O1'ⁱⁱ	90.90 (15)	C1ⁱ—C2—H2B	108.9
N1'ⁱⁱ—Cu2—O3'	95.62 (11)	H2A—C2—H2B	107.7
N1'—Cu2—O3'	95.62 (11)	C1'—C2'—C1'ⁱⁱ	114.4 (5)
O1'—Cu2—O3'	88.69 (10)	C1'—C2'—H2'A	108.7
O1'ⁱⁱ—Cu2—O3'	88.69 (10)	C1'ⁱⁱ—C2'—H2'A	108.7
C3—O1—Cu1	124.7 (2)	C1'—C2'—H2'B	108.7
C3'—O1'—Cu2	126.3 (2)	C1'ⁱⁱ—C2'—H2'B	108.7
Cu1—O3—H3	109.6	H2'A—C2'—H2'B	107.6
Cu2—O3'—H3'	109.5	O2—C3—O1	125.1 (3)
C1—N1—Cu1	118.3 (2)	O2—C3—C4	116.3 (3)
C1—N1—H1A	107.9	O1—C3—C4	118.6 (3)
Cu1—N1—H1A	107.7	O2'—C3'—O1'	126.4 (3)
C1—N1—H1B	107.7	O2'—C3'—C4'	115.9 (3)
Cu1—N1—H1B	107.7	O1'—C3'—C4'	117.7 (3)
H1A—N1—H1B	107.1	C4'—C4—C3	123.2 (3)
C1'—N1'—Cu2	118.1 (2)	C4'—C4—H4	118.4
C1'—N1'—H1'A	107.9	C3—C4—H4	118.4
Cu2—N1'—H1'A	107.7	C4—C4'—C3'	123.3 (3)
C1'—N1'—H1'B	107.8	C4—C4'—H4'	118.4
Cu2—N1'—H1'B	107.6	C3'—C4'—H4'	118.4
H1'A—N1'—H1'B	107.2	H4A—O4—H4B	101.0
N1—C1—C2	111.8 (4)

N1—Cu1—O1—C3	−55.8 (3)	Cu2—N1'—C1'—C2'	60.7 (4)
O1ⁱ—Cu1—O1—C3	117.8 (2)	N1—C1—C2—C1ⁱ	67.9 (6)
O3—Cu1—O1—C3	−153.5 (3)	N1'—C1'—C2'—C1'ⁱⁱ	−66.0 (6)
N1'—Cu2—O1'—C3'	63.3 (3)	Cu1—O1—C3—O2	−9.0 (5)
O1'ⁱⁱ—Cu2—O1'—C3'	−112.3 (3)	Cu1—O1—C3—C4	169.0 (2)
O3'—Cu2—O1'—C3'	159.0 (3)	Cu2—O1'—C3'—O2'	9.9 (5)
N1ⁱ—Cu1—N1—C1	42.8 (3)	Cu2—O1'—C3'—C4'	−169.8 (2)
O1—Cu1—N1—C1	−143.6 (3)	O2—C3—C4—C4'	137.3 (3)
O3—Cu1—N1—C1	−55.1 (3)	O1—C3—C4—C4'	−40.9 (4)
N1'ⁱⁱ—Cu2—N1'—C1'	−46.1 (3)	C3—C4—C4'—C3'	178.8 (3)
O1'—Cu2—N1'—C1'	138.2 (2)	O2'—C3'—C4'—C4	−142.2 (3)
O3'—Cu2—N1'—C1'	49.5 (3)	O1'—C3'—C4'—C4	37.5 (5)
Cu1—N1—C1—C2	−59.6 (4)

Symmetry codes: (i) −x+1, y, z; (ii) −x, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2′	0.87	2.17	2.887 (5)	140
O3—H3···O2ⁱⁱⁱ	0.85	1.88	2.713 (3)	166
O3′—H3′···O2′^iv	0.85	1.91	2.708 (3)	156
N1—H1A···O1^v	0.90	2.20	3.083 (4)	167
N1′—H1′A···O4^vi	0.90	2.25	3.071 (5)	151
N1′—H1′B···O1′^vii	0.90	2.26	3.135 (3)	164
O4—H4B···O2^viii	0.86	1.99	2.785 (4)	153

Symmetry codes: (iii) −x+1, −y+1, z−1/2; (iv) −x, −y, z+1/2; (v) x, −y+1, z+1/2; (vi) x, −y, z+1/2; (vii) x, −y, z−1/2; (viii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	[Cu(C₄H₂O₄)(C₃H₁₀N₂)(H₂O)]·H₂O
M_r	286.76
Crystal system, space group	Orthorhombic, Pmc2₁
Temperature (K)	293
a, b, c (Å)	14.993 (3), 8.0948 (17), 9.259 (2)
V (Å³)	1123.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.96
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS IIC image-plate system diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2000)
T_min, T_max	0.543, 0.82
No. of measured, independent and observed [I > 2σ(I)] reflections	10226, 3345, 2913
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.765

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.096, 1.14
No. of reflections	3345
No. of parameters	154
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.82
Absolute structure	Flack (1983), 1415 Friedel pairs
Absolute structure parameter	0.011 (18)

Computer programs: CrystalClear (Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Selected geometric parameters (Å, º) top

Cu1—N1	2.019 (3)	Cu2—N1'	2.010 (3)
Cu1—O1	2.024 (2)	Cu2—O1'	2.015 (3)
Cu1—O3	2.180 (3)	Cu2—O3'	2.270 (3)

N1ⁱ—Cu1—N1	90.42 (18)	N1'ⁱⁱ—Cu2—N1'	89.83 (19)
N1—Cu1—O1	88.93 (11)	N1'—Cu2—O1'	89.47 (10)
N1—Cu1—O1ⁱ	173.62 (11)	N1'—Cu2—O1'ⁱⁱ	175.68 (13)
O1—Cu1—O1ⁱ	91.00 (14)	O1'—Cu2—O1'ⁱⁱ	90.90 (15)
N1—Cu1—O3	97.70 (11)	N1'—Cu2—O3'	95.62 (11)
O1—Cu1—O3	88.68 (10)	O1'—Cu2—O3'	88.69 (10)

Symmetry codes: (i) −x+1, y, z; (ii) −x, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2'	0.87	2.17	2.887 (5)	140
O3—H3···O2ⁱⁱⁱ	0.85	1.88	2.713 (3)	166
O3'—H3'···O2'^iv	0.85	1.91	2.708 (3)	156
N1—H1A···O1^v	0.90	2.20	3.083 (4)	167
N1'—H1'A···O4^vi	0.90	2.25	3.071 (5)	151
N1'—H1'B···O1'^vii	0.90	2.26	3.135 (3)	164
O4—H4B···O2^viii	0.86	1.99	2.785 (4)	153

Symmetry codes: (iii) −x+1, −y+1, z−1/2; (iv) −x, −y, z+1/2; (v) x, −y+1, z+1/2; (vi) x, −y, z+1/2; (vii) x, −y, z−1/2; (viii) x, y, z−1.

Acknowledgements

The authors thank Professor Lennart Sjölin for his efforts to establish research collaboration between the University of the West Indies – Mona Campus and Göteborg University.

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