2-Oxo-1,2-dihydro­pyrimidin-3-ium di-μ-chlorido-bis­{dichloridobis[pyrimidin-2(1H)-one-κN3]cuprate(II)} dihydrate

Kurawa, M.A.; Adams, C.J.; Orpen, A.G.

doi:10.1107/S1600536808017455

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages m924-m925

doi:10.1107/S1600536808017455

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2-Oxo-1,2-dihydropyrimidin-3-ium di-μ-chlorido-bis{dichloridobis[pyrimidin-2(1H)-one-κN³]cuprate(II)} dihydrate

Mukhtar A. Kurawa,^a Christopher J. Adams ^a and A. Guy Orpen ^a ^*

^aSchool of Chemistry, University of Bristol, Bristol BS8 1TS, England
^*Correspondence e-mail: guy.orpen@bristol.ac.uk

(Received 9 June 2008; accepted 10 June 2008; online 13 June 2008)

The asymmetric unit of the title compound, (C₄H₅N₂O)₂[Cu₂Cl₆(C₄H₄N₂O)₂]·2H₂O, consists of one cation, one half of a centrosymmetric dianion and one water molecule. The centrosymmetric dianion formed by dimerization in the crystal structure has neutral pyrimidin-2-one ligands coordinated to each copper(II) centre through Cu—N bonds. The Cu atoms each have a distorted trigonal bipyramidal geometry, with the N atom of the pyrimidin-2-one ligand in an axial position, and dimerize by sharing two equatorial Cl atoms. N—H⋯Cl, O—H⋯Cl and N—H⋯O hydrogen bonds connect the anions, cations and water molecules, forming a three-dimensional network.

Related literature

The anion has an essentially similar coordination environment to that of the related compound [{(C₅H₅N)NH₂}CuCl₃]₂ which has 3-aminopyridinium cations (Blanchette & Willett, 1988 ) as the nitrogen donors and is thus neutral, while the crystal structure of the cation was described by Furberg & Aas (1975 ) as its chloride salt.

Experimental

Crystal data

(C₄H₅N₂O)₂[Cu₂Cl₆(C₄H₄N₂O)₂]·2H₂O
M_r = 762.22
Triclinic, $[P \overline 1]$
a = 7.5924 (4) Å
b = 8.6401 (3) Å
c = 10.6349 (4) Å
α = 96.032 (3)°
β = 100.508 (4)°
γ = 102.035 (4)°
V = 663.39 (5) Å³
Z = 1
Mo Kα radiation
μ = 2.26 mm⁻¹
T = 100 (2) K
0.41 × 0.18 × 0.15 mm

Data collection

Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.433, T_max = 0.71
14528 measured reflections
3902 independent reflections
3269 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.069
S = 1.12
3902 reflections
180 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—N1	1.9989 (12)
Cu1—Cl3	2.2809 (4)
Cu1—Cl1	2.2830 (4)
Cu1—Cl2ⁱ	2.3942 (4)
Cu1—Cl2	2.6093 (4)
Symmetry code: (i) -x, -y+1, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯Cl1ⁱⁱ	0.86	2.56	3.4143 (14)	171
N3—H3A⋯O3ⁱⁱⁱ	0.86	1.86	2.7099 (18)	168
N4—H2A⋯Cl2^iv	0.86	2.30	3.1336 (14)	165
O3—H1⋯Cl1^v	0.815 (16)	2.428 (17)	3.2258 (13)	166 (2)
O3—H2⋯Cl3^vi	0.844 (17)	2.454 (18)	3.2653 (13)	162 (2)
Symmetry codes: (ii) x, y-1, z; (iii) x, y+1, z; (iv) x, y, z-1; (v) -x+1, -y+1, -z+1; (vi) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017455/sg2250sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017455/sg2250Isup2.hkl

checkCIF report

Comment top

N—H···Cl interactions have been extensively used in crystal engineering to design and synthesize materials with desired structures. We sought to further utilize these interactions by reacting 2-hydroxypyrimidine hydrochloride and copper(II) chloride in a 2:1 ratio with the aim of synthesizing [C₄H₅N₂O]₂[CuCl₄]. However, the title compound I was obtained, which crystallizes in the triclinic system with the P1 space group. The copper coordination centres are similar to those described by Blanchette and Willett (1988) in [{(C₅H₅N)NH₂}CuCl₃]₂. The H₂O molecules and the [C₄H₅N₂O]⁺ cations (having both N atoms protonated and the O atoms atom deprotonated) are packed between the anions along the c-axis, the water forming O—H···Cl bridges between the anions while the cations form N—H···Cl and N—H···O bonds with the anions and water molecules respectively (Fig. 2).

For related literature, see Blanchette & Willett (1988) and Furberg & Aas (1975).

Related literature top

The anion has an essentially similar coordination environment to that of the related compound [{(C₅H₅N)NH₂}CuCl₃]₂ which has 3-aminopyridinium cations (Blanchette & Willett, 1988) as the nitrogen donors and is thus neutral, while the crystal structure of the cation was described by Furberg & Aas (1975) as its chloride salt.

Experimental top

Copper(II) chloride dihydrate and 2-hydroxypyrimidine hydrochloride in a 1:2 molar ratio were dissolved in concentrated hydrochloric acid solution. The solution was left to evaporate slowly at room temperature and resulted in the formation of green crystals after a few days.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of I showing one dimeric dianion, one cation and a molecule of water of crystallization, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Packing of I in the ac plane, with O—H···Cl bridges between the water molecules and the dianions, N—H···O hydrogen bonds between cations and water molecules, and N—H···Cl hydrogen bonds between the anions and cations.

2-Oxo-1,2-dihydropyrimidin-3-ium di-µ-chlorido-bis{dichloridobis[pyrimidin-2(1H)-one-κN³]cuprate(II)} dihydrate top

Crystal data top

(C₄H₅N₂O)₂[Cu₂Cl₆(C₄H₄N₂O)₂]·2H₂O	Z = 1
M_r = 762.22	F(000) = 382
Triclinic, P1	D_x = 1.908 Mg m⁻³
a = 7.5924 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6401 (3) Å	Cell parameters from 10481 reflections
c = 10.6349 (4) Å	θ = 2.4–30.0°
α = 96.032 (3)°	µ = 2.26 mm⁻¹
β = 100.508 (4)°	T = 100 K
γ = 102.035 (4)°	Block, green
V = 663.39 (5) Å³	0.41 × 0.18 × 0.16 mm

Data collection top

Oxford Diffraction Gemini-R Ultra diffractometer	3902 independent reflections
Radiation source: fine-focus sealed tube	3269 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω (1° width) scans	θ_max = 30.1°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −10→10
T_min = 0.433, T_max = 0.71	k = −12→12
14528 measured reflections	l = −15→15

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0422P)² + 0.0753P] where P = (F_o² + 2F_c²)/3
3902 reflections	(Δ/σ)_max = 0.002
180 parameters	Δρ_max = 0.49 e Å⁻³
2 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

(C₄H₅N₂O)₂[Cu₂Cl₆(C₄H₄N₂O)₂]·2H₂O	γ = 102.035 (4)°
M_r = 762.22	V = 663.39 (5) Å³
Triclinic, P1	Z = 1
a = 7.5924 (4) Å	Mo Kα radiation
b = 8.6401 (3) Å	µ = 2.26 mm⁻¹
c = 10.6349 (4) Å	T = 100 K
α = 96.032 (3)°	0.41 × 0.18 × 0.16 mm
β = 100.508 (4)°

Data collection top

Oxford Diffraction Gemini-R Ultra diffractometer	3902 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	3269 reflections with I > 2σ(I)
T_min = 0.433, T_max = 0.71	R_int = 0.020
14528 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	2 restraints
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.49 e Å⁻³
3902 reflections	Δρ_min = −0.57 e Å⁻³
180 parameters

Special details top

Experimental. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.07237 (3)	0.45037 (2)	0.848449 (17)	0.01007 (6)
Cl1	−0.06435 (5)	0.63425 (4)	0.75599 (3)	0.01291 (8)
Cl2	0.19396 (5)	0.64570 (4)	1.06611 (3)	0.01065 (8)
Cl3	0.26769 (6)	0.45986 (5)	0.70847 (4)	0.01557 (9)
N1	0.18231 (18)	0.28152 (15)	0.92487 (12)	0.0099 (2)
N2	0.15847 (19)	0.00585 (15)	0.91842 (13)	0.0122 (3)
H2B	0.1020	−0.0912	0.8865	0.015*
N3	0.69462 (19)	0.93935 (16)	0.46681 (12)	0.0124 (3)
H3A	0.7819	1.0237	0.4760	0.015*
N4	0.43187 (19)	0.76169 (16)	0.34665 (13)	0.0137 (3)
H2A	0.3488	0.7298	0.2768	0.016*
O1	0.58355 (18)	0.96484 (15)	0.25699 (12)	0.0204 (3)
O2	−0.02211 (17)	0.10178 (14)	0.76366 (11)	0.0176 (2)
O3	0.93114 (18)	0.22792 (15)	0.49005 (12)	0.0198 (3)
C1	0.0983 (2)	0.12810 (17)	0.86166 (15)	0.0116 (3)
C2	0.3215 (2)	0.30666 (18)	1.02403 (14)	0.0119 (3)
H2C	0.3773	0.4116	1.0619	0.014*
C3	0.3900 (2)	0.18275 (18)	1.07546 (15)	0.0132 (3)
H3B	0.4917	0.2036	1.1436	0.016*
C4	0.3004 (2)	0.03050 (18)	1.02078 (15)	0.0129 (3)
H4A	0.3368	−0.0560	1.0538	0.016*
C5	0.5717 (2)	0.89360 (19)	0.34849 (15)	0.0135 (3)
C6	0.6850 (2)	0.85959 (19)	0.56744 (15)	0.0134 (3)
H6A	0.7744	0.8941	0.6433	0.016*
C7	0.5451 (2)	0.72742 (19)	0.56028 (15)	0.0141 (3)
H7A	0.5372	0.6718	0.6301	0.017*
C8	0.4167 (2)	0.68029 (19)	0.44567 (15)	0.0139 (3)
H8A	0.3194	0.5917	0.4373	0.017*
H1	0.947 (3)	0.268 (3)	0.4257 (19)	0.037 (7)*
H2	1.024 (3)	0.267 (3)	0.551 (2)	0.044 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01130 (11)	0.00927 (9)	0.00972 (10)	0.00265 (7)	0.00141 (7)	0.00270 (7)
Cl1	0.01491 (19)	0.01236 (16)	0.01204 (17)	0.00437 (13)	0.00135 (14)	0.00458 (12)
Cl2	0.01105 (17)	0.00891 (15)	0.01027 (16)	0.00021 (13)	0.00046 (13)	0.00112 (12)
Cl3	0.01575 (19)	0.01618 (18)	0.01615 (18)	0.00296 (14)	0.00692 (14)	0.00377 (14)
N1	0.0118 (6)	0.0074 (5)	0.0097 (6)	0.0012 (5)	0.0015 (5)	0.0009 (4)
N2	0.0136 (7)	0.0069 (5)	0.0160 (6)	0.0012 (5)	0.0042 (5)	0.0008 (5)
N3	0.0102 (6)	0.0135 (6)	0.0123 (6)	0.0010 (5)	0.0007 (5)	0.0024 (5)
N4	0.0115 (6)	0.0165 (6)	0.0101 (6)	0.0018 (5)	−0.0021 (5)	−0.0012 (5)
O1	0.0218 (7)	0.0265 (6)	0.0160 (6)	0.0084 (5)	0.0052 (5)	0.0100 (5)
O2	0.0184 (6)	0.0142 (5)	0.0158 (5)	0.0017 (5)	−0.0033 (5)	−0.0013 (4)
O3	0.0198 (7)	0.0203 (6)	0.0143 (6)	−0.0049 (5)	0.0001 (5)	0.0058 (5)
C1	0.0126 (7)	0.0089 (6)	0.0133 (7)	0.0014 (5)	0.0040 (6)	0.0013 (5)
C2	0.0122 (7)	0.0106 (7)	0.0122 (7)	0.0019 (6)	0.0025 (6)	0.0010 (5)
C3	0.0140 (8)	0.0136 (7)	0.0125 (7)	0.0049 (6)	0.0019 (6)	0.0025 (5)
C4	0.0149 (8)	0.0121 (7)	0.0149 (7)	0.0058 (6)	0.0059 (6)	0.0056 (6)
C5	0.0114 (8)	0.0157 (7)	0.0141 (7)	0.0052 (6)	0.0022 (6)	0.0023 (6)
C6	0.0139 (8)	0.0137 (7)	0.0115 (7)	0.0041 (6)	−0.0005 (6)	0.0009 (5)
C7	0.0160 (8)	0.0139 (7)	0.0119 (7)	0.0028 (6)	0.0022 (6)	0.0030 (5)
C8	0.0121 (8)	0.0128 (7)	0.0158 (7)	0.0020 (6)	0.0030 (6)	−0.0004 (6)

Geometric parameters (Å, º) top

Cu1—N1	1.9989 (12)	N4—H2A	0.8600
Cu1—Cl3	2.2809 (4)	O1—C5	1.2119 (19)
Cu1—Cl1	2.2830 (4)	O2—C1	1.221 (2)
Cu1—Cl2ⁱ	2.3942 (4)	O3—H1	0.815 (16)
Cu1—Cl2	2.6093 (4)	O3—H2	0.844 (17)
Cl2—Cu1ⁱ	2.3942 (4)	C2—C3	1.403 (2)
N1—C2	1.314 (2)	C2—H2C	0.9300
N1—C1	1.3854 (19)	C3—C4	1.361 (2)
N2—C4	1.349 (2)	C3—H3B	0.9300
N2—C1	1.3868 (19)	C4—H4A	0.9300
N2—H2B	0.8600	C6—C7	1.373 (2)
N3—C6	1.337 (2)	C6—H6A	0.9300
N3—C5	1.387 (2)	C7—C8	1.378 (2)
N3—H3A	0.8600	C7—H7A	0.9300
N4—C8	1.335 (2)	C8—H8A	0.9300
N4—C5	1.382 (2)

N1—Cu1—Cl3	88.53 (4)	O2—C1—N1	122.46 (14)
N1—Cu1—Cl1	177.38 (4)	O2—C1—N2	122.11 (14)
Cl3—Cu1—Cl1	91.956 (15)	N1—C1—N2	115.42 (13)
N1—Cu1—Cl2ⁱ	88.05 (4)	N1—C2—C3	123.13 (14)
Cl3—Cu1—Cl2ⁱ	157.928 (16)	N1—C2—H2C	118.4
Cl1—Cu1—Cl2ⁱ	90.538 (15)	C3—C2—H2C	118.4
N1—Cu1—Cl2	91.12 (4)	C4—C3—C2	116.78 (15)
Cl3—Cu1—Cl2	115.984 (15)	C4—C3—H3B	121.6
Cl1—Cu1—Cl2	90.982 (14)	C2—C3—H3B	121.6
Cl2ⁱ—Cu1—Cl2	85.883 (14)	N2—C4—C3	119.63 (14)
Cu1ⁱ—Cl2—Cu1	94.117 (14)	N2—C4—H4A	120.2
C2—N1—C1	120.92 (13)	C3—C4—H4A	120.2
C2—N1—Cu1	125.69 (10)	O1—C5—N4	123.48 (15)
C1—N1—Cu1	113.38 (10)	O1—C5—N3	123.19 (15)
C4—N2—C1	123.75 (13)	N4—C5—N3	113.30 (13)
C4—N2—H2B	118.1	N3—C6—C7	120.87 (15)
C1—N2—H2B	118.1	N3—C6—H6A	119.6
C6—N3—C5	123.65 (14)	C7—C6—H6A	119.6
C6—N3—H3A	118.2	C6—C7—C8	117.45 (15)
C5—N3—H3A	118.2	C6—C7—H7A	121.3
C8—N4—C5	124.63 (14)	C8—C7—H7A	121.3
C8—N4—H2A	117.7	N4—C8—C7	120.03 (15)
C5—N4—H2A	117.7	N4—C8—H8A	120.0
H1—O3—H2	109 (2)	C7—C8—H8A	120.0

N1—Cu1—Cl2—Cu1ⁱ	−87.97 (4)	C4—N2—C1—N1	−6.1 (2)
Cl3—Cu1—Cl2—Cu1ⁱ	−176.875 (16)	C1—N1—C2—C3	−2.4 (2)
Cl1—Cu1—Cl2—Cu1ⁱ	90.469 (15)	Cu1—N1—C2—C3	178.41 (11)
Cl2ⁱ—Cu1—Cl2—Cu1ⁱ	0.0	N1—C2—C3—C4	−2.5 (2)
Cl3—Cu1—N1—C2	92.08 (13)	C1—N2—C4—C3	1.5 (2)
Cl2ⁱ—Cu1—N1—C2	−109.72 (13)	C2—C3—C4—N2	2.9 (2)
Cl2—Cu1—N1—C2	−23.88 (13)	C8—N4—C5—O1	179.35 (16)
Cl3—Cu1—N1—C1	−87.19 (10)	C8—N4—C5—N3	−2.3 (2)
Cl2ⁱ—Cu1—N1—C1	71.00 (10)	C6—N3—C5—O1	−178.50 (16)
Cl2—Cu1—N1—C1	156.84 (10)	C6—N3—C5—N4	3.2 (2)
C2—N1—C1—O2	−174.50 (15)	C5—N3—C6—C7	−2.4 (2)
Cu1—N1—C1—O2	4.8 (2)	N3—C6—C7—C8	0.4 (2)
C2—N1—C1—N2	6.4 (2)	C5—N4—C8—C7	0.7 (2)
Cu1—N1—C1—N2	−174.26 (10)	C6—C7—C8—N4	0.4 (2)
C4—N2—C1—O2	174.79 (15)

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···Cl1ⁱⁱ	0.86	2.56	3.4143 (14)	171
N3—H3A···O3ⁱⁱⁱ	0.86	1.86	2.7099 (18)	168
N4—H2A···Cl2^iv	0.86	2.30	3.1336 (14)	165
O3—H1···Cl1^v	0.82 (2)	2.43 (2)	3.2258 (13)	166 (2)
O3—H2···Cl3^vi	0.84 (2)	2.45 (2)	3.2653 (13)	162 (2)

Symmetry codes: (ii) x, y−1, z; (iii) x, y+1, z; (iv) x, y, z−1; (v) −x+1, −y+1, −z+1; (vi) x+1, y, z.

Experimental details

Crystal data
Chemical formula	(C₄H₅N₂O)₂[Cu₂Cl₆(C₄H₄N₂O)₂]·2H₂O
M_r	762.22
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.5924 (4), 8.6401 (3), 10.6349 (4)
α, β, γ (°)	96.032 (3), 100.508 (4), 102.035 (4)
V (Å³)	663.39 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.26
Crystal size (mm)	0.41 × 0.18 × 0.16

Data collection
Diffractometer	Oxford Diffraction Gemini-R Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.433, 0.71
No. of measured, independent and observed [I > 2σ(I)] reflections	14528, 3902, 3269
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.069, 1.12
No. of reflections	3902
No. of parameters	180
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.57

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—N1	1.9989 (12)	Cu1—Cl2ⁱ	2.3942 (4)
Cu1—Cl3	2.2809 (4)	Cu1—Cl2	2.6093 (4)
Cu1—Cl1	2.2830 (4)

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···Cl1ⁱⁱ	0.86	2.56	3.4143 (14)	170.8
N3—H3A···O3ⁱⁱⁱ	0.86	1.86	2.7099 (18)	168.1
N4—H2A···Cl2^iv	0.86	2.30	3.1336 (14)	164.7
O3—H1···Cl1^v	0.815 (16)	2.428 (17)	3.2258 (13)	166 (2)
O3—H2···Cl3^vi	0.844 (17)	2.454 (18)	3.2653 (13)	162 (2)

Symmetry codes: (ii) x, y−1, z; (iii) x, y+1, z; (iv) x, y, z−1; (v) −x+1, −y+1, −z+1; (vi) x+1, y, z.

Acknowledgements

MAK thanks Bayero University, Kano, Nigeria, for funding. Oxford Diffraction Ltd are thanked for the loan of an Oxford Gemini R Ultra diffractometer to the University of Bristol.

References

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Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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