Bis(di-2-pyridylmethane­diol-κ3N,O,N′)copper(II) bis­(tetra­fluorido­borate) dihydrate

Brown, K.L.; Crundwell, G.; Westcott, B.L.

doi:10.1107/S1600536809016973

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page m642

doi:10.1107/S1600536809016973

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Bis(di-2-pyridylmethanediol-κ³N,O,N′)copper(II) bis(tetrafluoridoborate) dihydrate

Krystal L. Brown,^a Guy Crundwell ^a and Barry L. Westcott ^a ^*

^aDepartment of Chemistry and Biochemistry, Central Connecticut State University, New Britain, CT 06050, USA
^*Correspondence e-mail: westcottb@ccsu.edu

(Received 7 April 2009; accepted 5 May 2009; online 14 May 2009)

The title complex, [Cu(C₁₁H₁₀N₂O₂)₂](BF₄)₂·2H₂O, was isolated as a dihydrate from a 1:2 molar mixture of copper(II) tetrafluoridoborate hexahydrate with di-2-pyridyl ketone in aqueous solution. The centrosymmetric complex cation is structurally similar to that found in previously reported salts and exhibits Cu—O bonds deviating by 25 degrees from an octahedral geometry by the so-called `off-axis angle' distortion. The BF₄⁻ anion exhibits a two site disorder of the fluorine atoms [ratio 0.210 (8):0.790 (8)].

Related literature

For related structures, see: Wang et al. (1986 ); Tangoulis et al. (1997 ); Yang et al. (1998 ); Tong et al. (1998 ); Serna et al. (1999 ); Reinoso et al. (2003 ); Li et al. (2005 ).

Experimental

Crystal data

[Cu(C₁₁H₁₀N₂O₂)₂](BF₄)₂·2H₂O
M_r = 677.61
Monoclinic, P 2₁ /c
a = 7.8147 (2) Å
b = 14.4225 (4) Å
c = 12.1840 (3) Å
β = 101.160 (3)°
V = 1347.26 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 293 K
0.8 × 0.6 × 0.6 mm

Data collection

Oxford Diffraction Sapphire CCD diffractometer
Absorption correction: multi-scan SCALE3 ABSPACK in CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]$ ) T_min = 0.474, T_max = 0.579
25175 measured reflections
5349 independent reflections
4145 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.192
S = 1.21
5349 reflections
219 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.72 e Å⁻³
Δρ_min = −1.03 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—N1ⁱ	2.0099 (19)
Cu1—N1	2.0099 (19)
Cu1—N2	2.0146 (19)
Cu1—N2ⁱ	2.0147 (19)
Cu1—O1	2.4312 (17)
Cu1—O1ⁱ	2.4312 (17)
Symmetry code: (i) -x, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	1.87	2.686 (3)	172
Symmetry codes: .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016973/fj2210sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016973/fj2210Isup2.hkl

checkCIF report

Related literature top

For related structures, see: Wang et al. (1986); Tangoulis et al. (1997); Yang et al. (1998); Tong et al. (1998); Serna et al. (1999); Reinoso et al. (2003); Li et al. (2005).

Experimental top

All chemicals and reagents were purchased from Aldrich and used as received. di-2-pyridyl ketone (2 mmol) and copper(II) tetrafluorborate hexahydrate (1 mmol) were combined in 40 ml of water and stirred for 30 minutes. The resulting violet crystals were isolated after 48 h by slow evaporation of the solution.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXLTL (Sheldrick, 2008).

Figures top

Fig. 1. ORTEP representation of the title complex. Thermal ellipsoids are drawn at the 30% probability level and H atoms have been omitted for clarity.

Bis(di-2-pyridylmethanediol-κ³N,O,N')copper(II) bis(tetrafluoroidborate) dihydrate top

Crystal data top

[Cu(C₁₁H₁₀N₂O₂)₂](BF₄)₂·2H₂O	F(000) = 686
M_r = 677.61	D_x = 1.670 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5349 reflections
a = 7.8147 (2) Å	θ = 3.8–32.0°
b = 14.4225 (4) Å	µ = 0.91 mm⁻¹
c = 12.1840 (3) Å	T = 293 K
β = 101.160 (3)°	Parallelpiped, violet
V = 1347.26 (6) Å³	0.8 × 0.6 × 0.6 mm
Z = 2

Data collection top

Oxford Diffraction Sapphire CCD diffractometer	5349 independent reflections
Radiation source: fine-focus sealed tube	4145 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 34.7°, θ_min = 3.9°
Absorption correction: multi-scan SCALE3 ABSPACK in CrysAlis RED (Oxford Diffraction, 2006)	h = −12→11
T_min = 0.474, T_max = 0.579	k = −22→22
25175 measured reflections	l = −18→19

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.192	H atoms treated by a mixture of independent and constrained refinement
S = 1.21	w = 1/[σ^2^(F_o^2^) + (0.0959P)^2^ + 1.P] where P = (F_o^2^ + 2F_c^2^)/3
5349 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.72 e Å⁻³
10 restraints	Δρ_min = −1.03 e Å⁻³

Crystal data top

[Cu(C₁₁H₁₀N₂O₂)₂](BF₄)₂·2H₂O	V = 1347.26 (6) Å³
M_r = 677.61	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8147 (2) Å	µ = 0.91 mm⁻¹
b = 14.4225 (4) Å	T = 293 K
c = 12.1840 (3) Å	0.8 × 0.6 × 0.6 mm
β = 101.160 (3)°

Data collection top

Oxford Diffraction Sapphire CCD diffractometer	5349 independent reflections
Absorption correction: multi-scan SCALE3 ABSPACK in CrysAlis RED (Oxford Diffraction, 2006)	4145 reflections with I > 2σ(I)
T_min = 0.474, T_max = 0.579	R_int = 0.036
25175 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	10 restraints
wR(F²) = 0.192	H atoms treated by a mixture of independent and constrained refinement
S = 1.21	Δρ_max = 0.72 e Å⁻³
5349 reflections	Δρ_min = −1.03 e Å⁻³
219 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. Hydrogen atoms were included in calculated positions for the ring carbons on the dpk ligand (0.93Å for sp² carbons) and were included in the refinement in riding motion approximation with U_iso = 1.2U_eq of the carrier atom for sp² carbons. Oxygen hydrogens were found in difference maps.

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	0.0000	0.0000	0.5000	0.02185 (12)
C1	0.2975 (3)	0.04790 (18)	0.3891 (2)	0.0289 (5)
H1	0.2514	0.0035	0.3363	0.035*
C2	0.4472 (4)	0.0936 (2)	0.3777 (2)	0.0335 (5)
H2A	0.5001	0.0810	0.3172	0.040*
C3	0.5190 (4)	0.1586 (2)	0.4571 (2)	0.0348 (5)
H3	0.6217	0.1894	0.4517	0.042*
C4	0.4334 (3)	0.17694 (18)	0.5455 (2)	0.0310 (5)
H4	0.4780	0.2203	0.6001	0.037*
C5	0.2824 (3)	0.12975 (15)	0.55022 (18)	0.0243 (4)
C6	0.1798 (3)	0.14291 (15)	0.64412 (18)	0.0240 (4)
C7	0.1983 (3)	0.05478 (15)	0.71483 (18)	0.0228 (4)
C8	0.2869 (4)	0.05111 (17)	0.8236 (2)	0.0294 (5)
H8	0.3411	0.1036	0.8587	0.035*
C9	0.2936 (4)	−0.03360 (19)	0.8802 (2)	0.0322 (5)
H9	0.3511	−0.0383	0.9543	0.039*
C10	0.2138 (4)	−0.11005 (17)	0.8244 (2)	0.0289 (4)
H10	0.2176	−0.1671	0.8604	0.035*
C11	0.1283 (3)	−0.10113 (16)	0.71447 (19)	0.0250 (4)
H11	0.0746	−0.1529	0.6772	0.030*
N1	0.2158 (3)	0.06543 (13)	0.47416 (15)	0.0230 (3)
N2	0.1204 (3)	−0.02000 (13)	0.65999 (15)	0.0214 (3)
O1	0.0028 (2)	0.15157 (12)	0.58765 (14)	0.0252 (3)
O2	0.2355 (3)	0.21705 (12)	0.71285 (15)	0.0310 (4)
H2	0.2214	0.2651	0.6763	0.047*
H50	−0.064 (5)	0.153 (3)	0.633 (3)	0.034 (9)*
H51	0.181 (7)	0.416 (4)	0.599 (4)	0.058 (13)*
H52	0.133 (6)	0.354 (3)	0.529 (4)	0.044 (11)*
O3	0.2110 (4)	0.36785 (16)	0.5814 (2)	0.0419 (5)
B1	0.8127 (4)	0.13674 (19)	0.8480 (2)	0.0302 (5)	0.790 (8)
F1	0.7868 (2)	0.16783 (13)	0.73741 (13)	0.0381 (4)	0.790 (8)
F2	0.8638 (9)	0.0451 (3)	0.8536 (8)	0.0471 (13)	0.790 (8)
F3	0.9557 (7)	0.1892 (2)	0.9056 (3)	0.0674 (14)	0.790 (8)
F4	0.6729 (5)	0.1531 (3)	0.8951 (3)	0.0661 (12)	0.790 (8)
B1B	0.8127 (4)	0.13674 (19)	0.8480 (2)	0.0302 (5)	0.210 (8)
F1B	0.7868 (2)	0.16783 (13)	0.73741 (13)	0.0381 (4)	0.210 (8)
F2B	0.894 (4)	0.0519 (14)	0.854 (3)	0.0471 (13)	0.210 (8)
F3B	0.866 (3)	0.1927 (9)	0.9307 (11)	0.0674 (14)	0.210 (8)
F4B	0.6394 (16)	0.1147 (11)	0.8558 (12)	0.0661 (12)	0.210 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0261 (2)	0.02088 (19)	0.01787 (18)	−0.00313 (13)	0.00248 (13)	−0.00088 (12)
C1	0.0302 (11)	0.0331 (12)	0.0238 (10)	−0.0027 (9)	0.0066 (8)	0.0000 (8)
C2	0.0302 (12)	0.0398 (14)	0.0323 (12)	−0.0002 (10)	0.0109 (9)	0.0049 (10)
C3	0.0271 (12)	0.0358 (13)	0.0423 (14)	−0.0049 (9)	0.0088 (10)	0.0050 (11)
C4	0.0308 (12)	0.0257 (10)	0.0350 (12)	−0.0068 (9)	0.0024 (9)	0.0008 (9)
C5	0.0271 (10)	0.0209 (9)	0.0234 (9)	−0.0013 (7)	0.0016 (7)	0.0019 (7)
C6	0.0313 (11)	0.0184 (8)	0.0210 (9)	−0.0036 (7)	0.0016 (7)	−0.0010 (7)
C7	0.0248 (10)	0.0206 (9)	0.0223 (9)	−0.0026 (7)	0.0030 (7)	−0.0012 (7)
C8	0.0352 (12)	0.0263 (10)	0.0246 (10)	−0.0040 (9)	0.0006 (8)	−0.0005 (8)
C9	0.0397 (13)	0.0323 (12)	0.0222 (10)	−0.0016 (10)	0.0004 (9)	0.0025 (9)
C10	0.0351 (12)	0.0249 (10)	0.0259 (10)	−0.0006 (9)	0.0037 (9)	0.0046 (8)
C11	0.0259 (10)	0.0206 (9)	0.0285 (10)	−0.0024 (7)	0.0053 (8)	0.0008 (7)
N1	0.0239 (8)	0.0236 (8)	0.0213 (8)	−0.0030 (6)	0.0036 (6)	0.0005 (6)
N2	0.0241 (8)	0.0198 (7)	0.0201 (7)	−0.0016 (6)	0.0035 (6)	−0.0003 (6)
O1	0.0270 (8)	0.0252 (7)	0.0227 (7)	0.0009 (6)	0.0026 (6)	0.0011 (6)
O2	0.0455 (11)	0.0198 (7)	0.0257 (8)	−0.0050 (7)	0.0019 (7)	−0.0033 (6)
O3	0.0584 (14)	0.0259 (9)	0.0390 (11)	0.0041 (9)	0.0035 (10)	0.0029 (8)
B1	0.0412 (15)	0.0245 (11)	0.0250 (11)	0.0042 (10)	0.0064 (10)	0.0002 (9)
F1	0.0457 (10)	0.0417 (9)	0.0268 (7)	0.0064 (7)	0.0072 (6)	0.0068 (6)
F2	0.069 (3)	0.0238 (11)	0.0477 (10)	0.0088 (16)	0.010 (2)	0.0005 (10)
F3	0.094 (3)	0.0412 (13)	0.0503 (17)	−0.0201 (19)	−0.0284 (19)	0.0030 (12)
F4	0.084 (2)	0.072 (3)	0.054 (2)	0.0369 (19)	0.0436 (18)	0.0173 (17)
B1B	0.0412 (15)	0.0245 (11)	0.0250 (11)	0.0042 (10)	0.0064 (10)	0.0002 (9)
F1B	0.0457 (10)	0.0417 (9)	0.0268 (7)	0.0064 (7)	0.0072 (6)	0.0068 (6)
F2B	0.069 (3)	0.0238 (11)	0.0477 (10)	0.0088 (16)	0.010 (2)	0.0005 (10)
F3B	0.094 (3)	0.0412 (13)	0.0503 (17)	−0.0201 (19)	−0.0284 (19)	0.0030 (12)
F4B	0.084 (2)	0.072 (3)	0.054 (2)	0.0369 (19)	0.0436 (18)	0.0173 (17)

Geometric parameters (Å, º) top

Cu1—N1ⁱ	2.0099 (19)	C6—C7	1.527 (3)
Cu1—N1	2.0099 (19)	C7—N2	1.350 (3)
Cu1—N2	2.0146 (19)	C7—C8	1.372 (3)
Cu1—N2ⁱ	2.0147 (19)	C8—C9	1.399 (4)
Cu1—O1	2.4312 (17)	C8—H8	0.9300
Cu1—O1ⁱ	2.4312 (17)	C9—C10	1.379 (4)
C1—N1	1.343 (3)	C9—H9	0.9300
C1—C2	1.373 (4)	C10—C11	1.382 (3)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.385 (4)	C11—N2	1.341 (3)
C2—H2A	0.9300	C11—H11	0.9300
C3—C4	1.399 (4)	O1—H50	0.83 (4)
C3—H3	0.9300	O2—H2	0.8200
C4—C5	1.373 (3)	O3—H51	0.78 (5)
C4—H4	0.9300	O3—H52	0.82 (5)
C5—N1	1.343 (3)	B1—F4	1.350 (4)
C5—C6	1.531 (3)	B1—F2	1.378 (5)
C6—O2	1.376 (3)	B1—F1	1.397 (3)
C6—O1	1.427 (3)	B1—F3	1.417 (5)

N1ⁱ—Cu1—N1	179.999 (1)	O1—C6—C5	104.48 (17)
N1ⁱ—Cu1—N2	91.74 (8)	C7—C6—C5	108.21 (18)
N1—Cu1—N2	88.27 (8)	N2—C7—C8	122.8 (2)
N1ⁱ—Cu1—N2ⁱ	88.26 (8)	N2—C7—C6	113.67 (19)
N1—Cu1—N2ⁱ	91.73 (8)	C8—C7—C6	123.5 (2)
N2—Cu1—N2ⁱ	180.0	C7—C8—C9	118.3 (2)
N1ⁱ—Cu1—O1	106.84 (7)	C7—C8—H8	120.9
N1—Cu1—O1	73.16 (7)	C9—C8—H8	120.9
N2—Cu1—O1	74.99 (7)	C10—C9—C8	119.0 (2)
N2ⁱ—Cu1—O1	105.01 (7)	C10—C9—H9	120.5
N1ⁱ—Cu1—O1ⁱ	73.16 (7)	C8—C9—H9	120.5
N1—Cu1—O1ⁱ	106.84 (7)	C11—C10—C9	119.4 (2)
N2—Cu1—O1ⁱ	105.01 (7)	C11—C10—H10	120.3
N2ⁱ—Cu1—O1ⁱ	74.99 (7)	C9—C10—H10	120.3
O1—Cu1—O1ⁱ	180.00 (8)	N2—C11—C10	121.9 (2)
N1—C1—C2	122.0 (2)	N2—C11—H11	119.1
N1—C1—H1	119.0	C10—C11—H11	119.1
C2—C1—H1	119.0	C5—N1—C1	118.9 (2)
C1—C2—C3	119.5 (2)	C5—N1—Cu1	116.18 (15)
C1—C2—H2A	120.2	C1—N1—Cu1	124.86 (16)
C3—C2—H2A	120.2	C11—N2—C7	118.63 (19)
C2—C3—C4	118.4 (2)	C11—N2—Cu1	124.89 (15)
C2—C3—H3	120.8	C7—N2—Cu1	116.48 (15)
C4—C3—H3	120.8	C6—O1—Cu1	93.35 (12)
C5—C4—C3	118.8 (2)	C6—O1—H50	111 (3)
C5—C4—H4	120.6	Cu1—O1—H50	111 (3)
C3—C4—H4	120.6	C6—O2—H2	109.5
N1—C5—C4	122.3 (2)	H51—O3—H52	103 (5)
N1—C5—C6	114.34 (19)	F4—B1—F2	113.4 (4)
C4—C5—C6	123.3 (2)	F4—B1—F1	112.1 (3)
O2—C6—O1	112.86 (19)	F2—B1—F1	110.0 (4)
O2—C6—C7	108.62 (18)	F4—B1—F3	108.8 (3)
O1—C6—C7	108.78 (18)	F2—B1—F3	107.1 (4)
O2—C6—C5	113.67 (19)	F1—B1—F3	105.0 (3)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.87	2.686 (3)	172

Experimental details

Crystal data
Chemical formula	[Cu(C₁₁H₁₀N₂O₂)₂](BF₄)₂·2H₂O
M_r	677.61
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.8147 (2), 14.4225 (4), 12.1840 (3)
β (°)	101.160 (3)
V (Å³)	1347.26 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.8 × 0.6 × 0.6

Data collection
Diffractometer	Oxford Diffraction Sapphire CCD diffractometer
Absorption correction	Multi-scan SCALE3 ABSPACK in CrysAlis RED (Oxford Diffraction, 2006)
T_min, T_max	0.474, 0.579
No. of measured, independent and observed [I > 2σ(I)] reflections	25175, 5349, 4145
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.801

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.192, 1.21
No. of reflections	5349
No. of parameters	219
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.72, −1.03

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXLTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—N1ⁱ	2.0099 (19)	Cu1—N2ⁱ	2.0147 (19)
Cu1—N1	2.0099 (19)	Cu1—O1	2.4312 (17)
Cu1—N2	2.0146 (19)	Cu1—O1ⁱ	2.4312 (17)

N1ⁱ—Cu1—N1	179.999 (1)	N2—Cu1—O1	74.99 (7)
N1ⁱ—Cu1—N2	91.74 (8)	N2ⁱ—Cu1—O1	105.01 (7)
N1—Cu1—N2	88.27 (8)	N1ⁱ—Cu1—O1ⁱ	73.16 (7)
N1ⁱ—Cu1—N2ⁱ	88.26 (8)	N1—Cu1—O1ⁱ	106.84 (7)
N1—Cu1—N2ⁱ	91.73 (8)	N2—Cu1—O1ⁱ	105.01 (7)
N2—Cu1—N2ⁱ	180.0	N2ⁱ—Cu1—O1ⁱ	74.99 (7)
N1ⁱ—Cu1—O1	106.84 (7)	O1—Cu1—O1ⁱ	180.00 (8)
N1—Cu1—O1	73.16 (7)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.87	2.686 (3)	172.0

Acknowledgements

The diffractometer was purchased with funding from the National Science Foundation (NSF # 0420322). Additional funding is from a CSUAAUP research grant.

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