Poly[ethyl­enediammonium [cuprate(II)-μ4-benzene-1,2,4,5-tetra­carboxyl­ato-κ4O:O′:O′′:O′′′] 2.5-hydrate]

Rafizadeh, M.; Amani, V.; Dehghan, L.; Azadbakht, F.; Sahlolbei, E.

doi:10.1107/S1600536807025834

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Poly[ethylenediammonium [cuprate(II)-μ₄-benzene-1,2,4,5-tetracarboxylato-κ⁴O:O′:O′′:O′′′] 2.5-hydrate]

M. Rafizadeh, V. Amani, L. Dehghan, F. Azadbakht and E. Sahlolbei

The asymmetric unit of the title compound, {(C₂H₁₀N₂)[Cu(C₁₀H₂O₈)]·2.5H₂O}_n, contains one cuprate(II)-μ₄-benzene-1,2,4,5-tetracarboxylate anion, one ethylenediammonium cation and two and a half water molecules. The Cu atom is four-coordinated by four O atoms from four benzene-1,2,4,5-tetracarboxylate anions. Intra- and intermolecular O—H

O and N—H

O hydrogen bonds in the formation of a supramolecular structure. One of the water molecules is disordered equally over two sites.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025834/hk2258sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025834/hk2258Isup2.hkl Contains datablock I

CCDC reference: 654724

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Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
Disorder in solvent or counterion
R factor = 0.037
wR factor = 0.100
Data-to-parameter ratio = 22.6

checkCIF/PLATON results

No syntax errors found



Alert level A
ABSMU01_ALERT_1_A  The ratio of given/expected absorption coefficient lies
               outside the range 0.90 <> 1.10
            Calculated value of mu =     5.918
            Value of mu given      =     1.479
CHEMW01_ALERT_1_A  The ratio of given/expected molecular weight as calculated
            from the _chemical_formula_sum lies outside
            the range 0.90 <> 1.10
            Calculated formula weight =  1683.2776
            Formula weight given      =   420.8200

Alert level C
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.25 Ratio
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................       7.00 Perc.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            O7  -CU1 -O1  -C1    -42.80  0.40   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         11
            O1  -CU1 -O7  -C9   -163.90  0.30   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         16

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C48 H68 Cu4 N8 O42
            Atom count from _chemical_formula_moiety:C12 H17 Cu1 N2 O10.5
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C48 H68 Cu4 N8 O42
            Atom count from the _atom_site data:  C12 H17 Cu1 N2 O10.5
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C48 H68 Cu4 N8 O42
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        192.00     48.00  144.00
           H        272.00     68.00  204.00
           Cu        16.00      4.00   12.00
           N         32.00      8.00   24.00
           O        168.00     42.00  126.00

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level G
PUBL017_ALERT_1_G The _publ_section_references section is missing or
            empty.

   0 ALERT level A = Data missing that is essential or data in wrong format
   1 ALERT level G = General alerts. Data that may be required is missing

Comment top

The self-assembly of metal ions with aromatic carboxylates is a rapidly developing research field of modern coordination chemistry, because of the aggregation of metal ions and these carboxylate ligands in versatile binding modes, such as monodentate, chelating bidentate, bridging bidentate and bridging tridentate. Hereby, benzene-1,2,4,5-tetracarboxylic acid (H₄BTC) is a good bridging ligand, and numerous complexes with H₄BTC anions have been prepared, such as those of cobalt (Hu et al., 2004; Fu et al., 2004; Cheng et al., 2002), nickel (Kim et al., 2003; Cheng et al., 2003), thallium (Day & Luehrs, 1988), copper (Kim et al., 2003; Yuan et al., 2005; Hao et al., 2004), zinc (Hou et al., 2004), iron (Chu et al., 2001) and manganese (Rochon & Massarweh, 2000; Hu et al., 2001). There are also compounds of the rare earth elements reported (Cao et al., 2002; Daiguebonne et al., 2003). The complex of benzene-1,2,4,5-tetracarboxylate containing organic ammonium cations are rare and may have interesting polymeric chemistry. Recently, we have reported the syntheses and crystal structure of a proton transfer system using (H₄BTC), with ethylenediamine (en), (BTC)(H₂en)₂.2H₂O, (Rafizadeh et al., 2006). We herein report the synthesis and crystal structure of the title compound, (I), which was synthesized by reaction of Cu(NO₃)₂.3H₂O and (BTC)(H₂en)₂.2H₂O.

The asymmetric unit of (I) contains one [Cu(C₁₀H₂O₈)] anion, one (N₂C₂H₁₀) cation and two and a half water molecules. The Cu atom is four-coordinated by four O atoms from four benzene-1,2,4,5-tetracarboxylate (btc) anions (Fig. 1). The Cu—O bond lengths and angles (Table 1) are within normal ranges (Kim et al., 2003; Yuan et al., 2005; Hao et al., 2004).

The intra- and intermolecular O—H—O and N—H···O hydrogen bonds (Table 2) seem to be effective in the stabilization of the crystal structure, resulting in the formation of a supramolecular structure (Fig. 2). Dipol-dipol and van der Waals interactions are also effective in the molecular packing.

Related literature top

For general backgroud, see: Hu et al. (2004, 2001); Fu et al. (2004); Cheng et al. (2002); Hou et al. (2004); Chu et al. (2001); Rochon & Massarweh (2000); Cao et al. (2002); Daiguebonne et al. (2003); Rafizadeh et al. (2006). For related literature, see: Kim et al. (2003); Yuan et al. (2005); Hao et al. (2004).

For related literature, see: Cheng et al. (2003); Day & Luehrs (1988).

Experimental top

For the preparation of the title compound, (I), a solution of (BTC)(H₂en)₂.2H₂O, (0.30 g, 0.73 mmol) in water (100 ml) was added to a solution of Cu(NO₃)₂.3H₂O (0.09 g, 0.365 mmol) in water (10 ml) and the resulting blue solution was stirred for 5 min at room temperature. Then, it was left to evaporate slowly at room temperature. After one week, blue prismatic crystals of (I) were isolated (yield; 0.13 g, 84.6%; decompose <562 K).

Structure description top

For related literature, see: Cheng et al. (2003); Day & Luehrs (1988).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level [symmetry codes: (i) 2 - x, y - 1/2, 2.5 - z, (ii) 2 - x, 1 - y, 2 - z, (iii) 2 - x, y - 1/2, 2.5 - z].
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

Poly[ethylenediammonium [copper(II)-µ₄-benzene-1,2,4,5-tetracarboxylato-κ⁴O:O':O'':O'''] 2.5-hydrate] top

Crystal data top

(C₂H₁₀N₂)[Cu(C₁₀H₂O₈)]·2.5H₂O	F(000) = 864
M_r = 420.82	D_x = 1.811 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5022 reflections
a = 7.3937 (5) Å	θ = 2.8–34.7°
b = 18.4414 (11) Å	µ = 1.48 mm⁻¹
c = 11.3607 (7) Å	T = 100 K
β = 94.783 (1)°	Cube, blue
V = 1543.64 (17) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker APEX II CCD area-detector diffractometer	5364 independent reflections
Radiation source: fine-focus sealed tube	4304 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
φ and ω scans	θ_max = 32.0°, θ_min = 2.1°
Absorption correction: multi-scan (APEX2; Bruker, 2005)	h = −11→11
T_min = 0.744, T_max = 0.751	k = −27→27
22717 measured reflections	l = −16→16

Refinement top

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)] = 0.037	Hydrogen site location: mixed
wR(F²) = 0.100	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0453P)² + 1.6005P] where P = (F_o² + 2F_c²)/3
5364 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.95 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

(C₂H₁₀N₂)[Cu(C₁₀H₂O₈)]·2.5H₂O	V = 1543.64 (17) Å³
M_r = 420.82	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3937 (5) Å	µ = 1.48 mm⁻¹
b = 18.4414 (11) Å	T = 100 K
c = 11.3607 (7) Å	0.20 × 0.20 × 0.20 mm
β = 94.783 (1)°

Data collection top

Bruker APEX II CCD area-detector diffractometer	5364 independent reflections
Absorption correction: multi-scan (APEX2; Bruker, 2005)	4304 reflections with I > 2σ(I)
T_min = 0.744, T_max = 0.751	R_int = 0.042
22717 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.01	Δρ_max = 0.95 e Å⁻³
5364 reflections	Δρ_min = −0.70 e Å⁻³
237 parameters

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	Occ. (<1)
Cu1	0.98260 (3)	0.743122 (11)	0.999045 (17)	0.00747 (7)
O1	1.00080 (18)	0.81812 (7)	1.12002 (11)	0.0109 (2)
O2	0.72149 (18)	0.85964 (7)	1.06384 (11)	0.0129 (2)
O3	1.04758 (17)	0.66759 (6)	1.11446 (11)	0.0096 (2)
O4	0.74826 (18)	0.65069 (7)	1.11395 (12)	0.0137 (3)
O5	0.96462 (18)	0.81928 (7)	0.87939 (11)	0.0107 (2)
O6	1.24867 (18)	0.85345 (7)	0.93744 (11)	0.0125 (2)
O7	0.92059 (17)	0.66741 (6)	0.88281 (11)	0.0092 (2)
O8	1.22206 (18)	0.65801 (7)	0.88507 (12)	0.0127 (3)
C1	0.8752 (2)	0.86592 (9)	1.11718 (14)	0.0085 (3)
C2	0.9277 (2)	0.93511 (9)	1.18051 (14)	0.0075 (3)
C3	0.8811 (2)	1.00135 (9)	1.12768 (15)	0.0085 (3)
H3A	0.8076	1.0025	1.0550	0.010*
C4	0.9066 (2)	0.63317 (9)	1.14322 (15)	0.0085 (3)
C5	0.9522 (2)	0.56440 (9)	1.21098 (14)	0.0070 (3)
C6	0.9048 (2)	0.49801 (9)	1.15800 (15)	0.0080 (3)
H6A	0.8307	0.4968	1.0856	0.010*
C7	1.0580 (2)	0.93391 (9)	0.81899 (14)	0.0078 (3)
C8	1.0975 (2)	0.86364 (9)	0.88280 (14)	0.0084 (3)
C9	1.0668 (2)	0.63647 (9)	0.85520 (14)	0.0081 (3)
C10	1.0338 (2)	0.56645 (9)	0.78862 (14)	0.0076 (3)
N1'	1.5660 (2)	0.65943 (8)	1.32091 (14)	0.0127 (3)
H1'C	1.6629	0.6490	1.3729	0.019*
H1'D	1.5774	0.6356	1.2518	0.019*
H1'E	1.4621	0.6450	1.3518	0.019*
N2'	1.4052 (2)	0.83478 (9)	1.17836 (14)	0.0137 (3)
H2'C	1.3108	0.8450	1.1243	0.021*
H2'D	1.5107	0.8500	1.1506	0.021*
H2'E	1.3887	0.8580	1.2473	0.021*
C1'	1.5587 (3)	0.73907 (10)	1.29853 (17)	0.0134 (3)
H1'A	1.6781	0.7563	1.2764	0.016*
H1'B	1.5303	0.7649	1.3711	0.016*
C2'	1.4139 (3)	0.75515 (10)	1.19949 (17)	0.0138 (3)
H2'A	1.4432	0.7299	1.1266	0.017*
H2'B	1.2948	0.7374	1.2211	0.017*
O1W	0.6201 (2)	0.42273 (8)	0.89555 (14)	0.0216 (3)
H1WA	0.5629	0.4100	0.9540	0.032*
H1WB	0.7244	0.4053	0.8861	0.032*
O2W	0.5892 (2)	0.57443 (9)	0.87753 (16)	0.0262 (4)
H2WA	0.5758	0.5287	0.8801	0.039*
H2WB	0.6951	0.5922	0.8909	0.039*
O3W	1.4335 (4)	0.99565 (15)	1.1305 (3)	0.0217 (6)	0.50
H3WA	1.3268	1.0023	1.1510	0.033*	0.50
H3WB	1.4755	1.0113	1.0679	0.033*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01489 (11)	0.00322 (10)	0.00438 (10)	0.00031 (7)	0.00120 (7)	0.00017 (7)
O1	0.0199 (6)	0.0058 (5)	0.0068 (5)	0.0024 (4)	0.0001 (4)	−0.0008 (4)
O2	0.0136 (6)	0.0148 (6)	0.0103 (6)	−0.0050 (5)	0.0009 (4)	−0.0029 (5)
O3	0.0151 (6)	0.0059 (5)	0.0078 (6)	−0.0009 (4)	0.0014 (4)	0.0014 (4)
O4	0.0139 (6)	0.0149 (6)	0.0123 (6)	0.0060 (5)	0.0020 (5)	0.0034 (5)
O5	0.0181 (6)	0.0062 (5)	0.0077 (6)	−0.0025 (4)	0.0012 (4)	0.0015 (4)
O6	0.0152 (6)	0.0114 (6)	0.0107 (6)	0.0033 (5)	0.0008 (5)	0.0023 (5)
O7	0.0135 (6)	0.0069 (5)	0.0073 (5)	0.0017 (4)	0.0015 (4)	−0.0014 (4)
O8	0.0140 (6)	0.0120 (6)	0.0123 (6)	−0.0046 (5)	0.0021 (5)	−0.0014 (5)
C1	0.0139 (8)	0.0068 (7)	0.0053 (7)	−0.0017 (5)	0.0040 (5)	0.0005 (5)
C2	0.0113 (7)	0.0046 (7)	0.0067 (7)	0.0003 (5)	0.0015 (5)	−0.0008 (5)
C3	0.0125 (8)	0.0062 (7)	0.0067 (7)	0.0005 (5)	0.0007 (5)	−0.0001 (6)
C4	0.0135 (8)	0.0057 (7)	0.0065 (7)	0.0014 (5)	0.0022 (5)	−0.0008 (5)
C5	0.0102 (7)	0.0058 (7)	0.0052 (7)	0.0002 (5)	0.0015 (5)	0.0007 (5)
C6	0.0107 (7)	0.0069 (7)	0.0066 (7)	0.0000 (5)	0.0012 (5)	0.0001 (6)
C7	0.0131 (7)	0.0048 (7)	0.0057 (7)	0.0004 (5)	0.0024 (5)	0.0012 (5)
C8	0.0155 (8)	0.0042 (7)	0.0060 (7)	0.0008 (5)	0.0032 (5)	−0.0004 (5)
C9	0.0144 (8)	0.0047 (7)	0.0054 (7)	−0.0005 (5)	0.0014 (5)	0.0002 (5)
C10	0.0109 (7)	0.0052 (7)	0.0067 (7)	−0.0005 (5)	0.0017 (5)	−0.0008 (5)
N1'	0.0127 (7)	0.0150 (7)	0.0105 (7)	0.0026 (5)	0.0006 (5)	0.0012 (5)
N2'	0.0142 (7)	0.0153 (7)	0.0116 (7)	0.0032 (5)	0.0008 (5)	0.0016 (6)
C1'	0.0142 (8)	0.0122 (8)	0.0132 (8)	0.0020 (6)	−0.0015 (6)	0.0016 (6)
C2'	0.0130 (8)	0.0147 (8)	0.0134 (8)	0.0016 (6)	−0.0013 (6)	0.0009 (6)
O1W	0.0207 (7)	0.0168 (7)	0.0282 (8)	−0.0001 (5)	0.0085 (6)	−0.0002 (6)
O2W	0.0165 (7)	0.0189 (7)	0.0429 (10)	0.0002 (5)	0.0012 (6)	0.0094 (7)
O3W	0.0218 (15)	0.0176 (14)	0.0245 (16)	−0.0036 (10)	−0.0049 (12)	0.0016 (12)

Geometric parameters (Å, º) top

Cu1—O3	1.9456 (12)	C7—C8	1.502 (2)
Cu1—O1	1.9466 (12)	C9—C10	1.506 (2)
Cu1—O7	1.9500 (12)	C10—C6ⁱⁱⁱ	1.393 (2)
Cu1—O5	1.9514 (12)	C10—C2^iv	1.402 (2)
O1—C1	1.279 (2)	N1'—C1'	1.491 (2)
O2—C1	1.248 (2)	N1'—H1'C	0.9100
O3—C4	1.285 (2)	N1'—H1'D	0.9100
O4—C4	1.233 (2)	N1'—H1'E	0.9100
O5—C8	1.276 (2)	N2'—C2'	1.489 (2)
O6—C8	1.247 (2)	N2'—H2'C	0.9100
O7—C9	1.284 (2)	N2'—H2'D	0.9100
O8—C9	1.235 (2)	N2'—H2'E	0.9100
C1—C2	1.500 (2)	C1'—C2'	1.516 (3)
C2—C3	1.392 (2)	C1'—H1'A	0.9900
C2—C10ⁱ	1.402 (2)	C1'—H1'B	0.9900
C3—C7ⁱⁱ	1.396 (2)	C2'—H2'A	0.9900
C3—H3A	0.9500	C2'—H2'B	0.9900
C4—C5	1.507 (2)	O1W—H1WA	0.8499
C5—C6	1.396 (2)	O1W—H1WB	0.8500
C5—C7ⁱ	1.399 (2)	O2W—H2WA	0.8501
C6—C10ⁱⁱⁱ	1.393 (2)	O2W—H2WB	0.8500
C6—H6A	0.9500	O3W—H3WA	0.8500
C7—C3ⁱⁱ	1.396 (2)	O3W—H3WB	0.8499
C7—C5^iv	1.399 (2)

O3—Cu1—O1	91.96 (5)	O8—C9—O7	124.89 (16)
O3—Cu1—O7	88.55 (5)	O8—C9—C10	121.42 (15)
O1—Cu1—O7	170.20 (6)	O7—C9—C10	113.55 (14)
O3—Cu1—O5	169.55 (6)	C6ⁱⁱⁱ—C10—C2^iv	120.14 (15)
O1—Cu1—O5	88.69 (5)	C6ⁱⁱⁱ—C10—C9	118.68 (14)
O7—Cu1—O5	92.59 (5)	C2^iv—C10—C9	120.87 (14)
C1—O1—Cu1	117.69 (11)	C1'—N1'—H1'C	109.5
C4—O3—Cu1	111.40 (11)	C1'—N1'—H1'D	109.5
C8—O5—Cu1	115.63 (11)	H1'C—N1'—H1'D	109.5
C9—O7—Cu1	109.17 (11)	C1'—N1'—H1'E	109.5
O2—C1—O1	125.32 (16)	H1'C—N1'—H1'E	109.5
O2—C1—C2	120.03 (15)	H1'D—N1'—H1'E	109.5
O1—C1—C2	114.60 (15)	C2'—N2'—H2'C	109.5
C3—C2—C10ⁱ	119.76 (15)	C2'—N2'—H2'D	109.5
C3—C2—C1	119.68 (15)	H2'C—N2'—H2'D	109.5
C10ⁱ—C2—C1	120.42 (14)	C2'—N2'—H2'E	109.5
C2—C3—C7ⁱⁱ	120.27 (15)	H2'C—N2'—H2'E	109.5
C2—C3—H3A	119.9	H2'D—N2'—H2'E	109.5
C7ⁱⁱ—C3—H3A	119.9	N1'—C1'—C2'	109.42 (15)
O4—C4—O3	125.01 (16)	N1'—C1'—H1'A	109.8
O4—C4—C5	121.65 (15)	C2'—C1'—H1'A	109.8
O3—C4—C5	113.21 (14)	N1'—C1'—H1'B	109.8
C6—C5—C7ⁱ	119.96 (15)	C2'—C1'—H1'B	109.8
C6—C5—C4	118.72 (14)	H1'A—C1'—H1'B	108.2
C7ⁱ—C5—C4	120.92 (14)	N2'—C2'—C1'	109.34 (15)
C10ⁱⁱⁱ—C6—C5	119.99 (15)	N2'—C2'—H2'A	109.8
C10ⁱⁱⁱ—C6—H6A	120.0	C1'—C2'—H2'A	109.8
C5—C6—H6A	120.0	N2'—C2'—H2'B	109.8
C3ⁱⁱ—C7—C5^iv	119.86 (15)	C1'—C2'—H2'B	109.8
C3ⁱⁱ—C7—C8	119.05 (15)	H2'A—C2'—H2'B	108.3
C5^iv—C7—C8	120.96 (14)	H1WA—O1W—H1WB	120.7
O6—C8—O5	125.05 (16)	H2WA—O2W—H2WB	118.9
O6—C8—C7	120.04 (15)	H3WA—O3W—H3WB	126.4
O5—C8—C7	114.85 (15)

O3—Cu1—O1—C1	−135.64 (12)	Cu1—O3—C4—C5	167.38 (10)
O7—Cu1—O1—C1	−42.8 (4)	O4—C4—C5—C6	63.2 (2)
O5—Cu1—O1—C1	54.80 (12)	O3—C4—C5—C6	−112.90 (17)
O1—Cu1—O3—C4	100.44 (11)	O4—C4—C5—C7ⁱ	−124.12 (19)
O7—Cu1—O3—C4	−69.76 (11)	O3—C4—C5—C7ⁱ	59.8 (2)
O5—Cu1—O3—C4	−166.2 (3)	C7ⁱ—C5—C6—C10ⁱⁱⁱ	−1.4 (3)
O3—Cu1—O5—C8	−35.5 (3)	C4—C5—C6—C10ⁱⁱⁱ	171.39 (15)
O1—Cu1—O5—C8	58.23 (12)	Cu1—O5—C8—O6	15.9 (2)
O7—Cu1—O5—C8	−131.50 (12)	Cu1—O5—C8—C7	−161.28 (11)
O3—Cu1—O7—C9	−70.78 (11)	C3ⁱⁱ—C7—C8—O6	−40.7 (2)
O1—Cu1—O7—C9	−163.9 (3)	C5^iv—C7—C8—O6	143.24 (17)
O5—Cu1—O7—C9	98.82 (11)	C3ⁱⁱ—C7—C8—O5	136.63 (17)
Cu1—O1—C1—O2	18.8 (2)	C5^iv—C7—C8—O5	−39.4 (2)
Cu1—O1—C1—C2	−158.60 (11)	Cu1—O7—C9—O8	−9.2 (2)
O2—C1—C2—C3	−42.1 (2)	Cu1—O7—C9—C10	166.48 (11)
O1—C1—C2—C3	135.45 (17)	O8—C9—C10—C6ⁱⁱⁱ	61.5 (2)
O2—C1—C2—C10ⁱ	142.31 (17)	O7—C9—C10—C6ⁱⁱⁱ	−114.33 (17)
O1—C1—C2—C10ⁱ	−40.1 (2)	O8—C9—C10—C2^iv	−124.93 (19)
C10ⁱ—C2—C3—C7ⁱⁱ	1.0 (3)	O7—C9—C10—C2^iv	59.2 (2)
C1—C2—C3—C7ⁱⁱ	−174.62 (15)	N1'—C1'—C2'—N2'	179.25 (14)
Cu1—O3—C4—O4	−8.5 (2)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+2, −y+2, −z+2; (iii) −x+2, −y+1, −z+2; (iv) x, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1′—H1′C···O2^v	0.91	2.18	2.921 (2)	138
N1′—H1′C···O5^v	0.91	2.30	2.993 (2)	132
N1′—H1′D···O4^vi	0.91	2.11	2.810 (2)	133
N1′—H1′E···O6ⁱ	0.91	1.92	2.799 (2)	161
N2′—H2′C···O6	0.91	2.14	2.902 (2)	141
N2′—H2′D···O2^vi	0.91	1.92	2.807 (2)	164
N2′—H2′E···O8ⁱ	0.91	2.09	2.810 (2)	135
O1W—H1WA···O2W^vii	0.85	2.32	3.116 (2)	157
O1W—H1WB···O3ⁱⁱⁱ	0.85	2.16	2.9784 (19)	162
O2W—H2WA···O1W	0.85	1.99	2.813 (2)	164
O2W—H2WB···O7	0.85	2.18	2.987 (2)	159

Symmetry codes: (i) x, −y+3/2, z+1/2; (iii) −x+2, −y+1, −z+2; (v) x+1, −y+3/2, z+1/2; (vi) x+1, y, z; (vii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	(C₂H₁₀N₂)[Cu(C₁₀H₂O₈)]·2.5H₂O
M_r	420.82
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.3937 (5), 18.4414 (11), 11.3607 (7)
β (°)	94.783 (1)
V (Å³)	1543.64 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.48
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEX II CCD area-detector
Absorption correction	Multi-scan (APEX2; Bruker, 2005)
T_min, T_max	0.744, 0.751
No. of measured, independent and observed [I > 2σ(I)] reflections	22717, 5364, 4304
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.746

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.01
No. of reflections	5364
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.95, −0.70

Computer programs: APEX2 (Bruker, 2005), APEX2, SHELXTL (Sheldrick, 1998), SHELXTL.

Selected geometric parameters (Å, º) top

Cu1—O3	1.9456 (12)	Cu1—O7	1.9500 (12)
Cu1—O1	1.9466 (12)	Cu1—O5	1.9514 (12)

O3—Cu1—O1	91.96 (5)	O3—Cu1—O5	169.55 (6)
O3—Cu1—O7	88.55 (5)	O1—Cu1—O5	88.69 (5)
O1—Cu1—O7	170.20 (6)	O7—Cu1—O5	92.59 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1'—H1'C···O2ⁱ	0.91	2.18	2.921 (2)	138
N1'—H1'C···O5ⁱ	0.91	2.30	2.993 (2)	132
N1'—H1'D···O4ⁱⁱ	0.91	2.11	2.810 (2)	133
N1'—H1'E···O6ⁱⁱⁱ	0.91	1.92	2.799 (2)	161
N2'—H2'C···O6	0.91	2.14	2.902 (2)	141
N2'—H2'D···O2ⁱⁱ	0.91	1.92	2.807 (2)	164
N2'—H2'E···O8ⁱⁱⁱ	0.91	2.09	2.810 (2)	135
O1W—H1WA···O2W^iv	0.85	2.32	3.116 (2)	157
O1W—H1WB···O3^v	0.85	2.16	2.9784 (19)	162
O2W—H2WA···O1W	0.85	1.99	2.813 (2)	164
O2W—H2WB···O7	0.85	2.18	2.987 (2)	159

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) x+1, y, z; (iii) x, −y+3/2, z+1/2; (iv) −x+1, −y+1, −z+2; (v) −x+2, −y+1, −z+2.

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