Bis[μ-3-(2-hydroxy­ethyl)-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-olato-κ3N,O:O]bis[aquachloridocopper(II)]

Deng, Y.; Li, Z.-S.; Sun, B.-W.

doi:10.1107/S1600536808028687

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1262

doi:10.1107/S1600536808028687

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Bis[μ-3-(2-hydroxyethyl)-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-olato-κ³N,O:O]bis[aquachloridocopper(II)]

Ying Deng,^a Zhong-Shu Li ^a and Bai-Wang Sun ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 13 August 2008; accepted 8 September 2008; online 13 September 2008)

In the dinuclear centrosymmetric copper(II) title compound, [Cu₂(C₁₁H₁₁N₂O₂)₂Cl₂(H₂O)₂], each Cu^II ion has a slightly distorted trigonal-bipyramidal geometry and is coordinated by one N and one O atom from one 3-(2-hydroxyethyl)-2-methyl-4-oxopyrido[1,2-a]pyrimidin-9-olate ligand, another O atom from the second ligand, one water molecule and one Cl atom. The crystal structure involves intermolecular C—H⋯Cl, O—H⋯Cl and O—H⋯O hydrogen bonds

Related literature

For related literature, see: Bayot et al. (2006 ); Chen et al. (2007 ); Sun et al. (2008 ); Wu et al. (2006 ).

Experimental

Crystal data

[Cu₂(C₁₁H₁₁N₂O₂)₂Cl₂(H₂O)₂]
M_r = 672.45
Monoclinic, P 2₁ /n
a = 9.391 (3) Å
b = 11.322 (3) Å
c = 11.905 (4) Å
β = 102.414 (18)°
V = 1236.2 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.99 mm⁻¹
T = 293 (2) K
0.25 × 0.12 × 0.08 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.890, T_max = 1.000 (expected range = 0.759–0.853)
12472 measured reflections
2826 independent reflections
2249 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.115
S = 1.01
2826 reflections
176 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5C⋯O2ⁱ	0.82	2.13	2.742 (4)	131
O5—H5D⋯O1ⁱⁱ	0.96	2.11	2.788 (4)	127
O2—H2A⋯Cl1ⁱⁱⁱ	0.75 (6)	2.37 (6)	3.078 (4)	158 (6)
C9—H9A⋯Cl1	0.96	2.49	3.275 (4)	139
C3—H3A⋯Cl1^iv	0.93	2.72	3.387 (4)	130
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) x-1, y, z; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x, -y+2, -z+1.

Data collection: CrystalClear (Rigaku, 2005); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808028687/sg2256sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028687/sg2256Isup2.hkl

checkCIF report

Comment top

In the past decade, much attention has been paid to the design and synthesis of self-assembling systems with organic ligands containing N and O donors (Bayot et al., 2006; Chen et al., 2007). Quinolin-8-ol is one such ligand and several crystal structures of complexes containing it have been reported (Wu et al., 2006). Our group has recently reported a new manganese compound with this 3-(2-hydroxyethyl)-2-methyl-4-oxopyrido[1,2-a]pyrimidin-9-olate ligands (Sun et al., 2008). We report here the synthesis and crystal structure of the title complex, (I) (Fig. 1). In (I), each Cu(II) ion has a slightly distorted trigonal–bipyramidal geometry and is coordinated by one N atoms and one O atom from one 3-(2-hydroxyethyl)-2-methyl-4-oxopyrido[1,2-a]pyrimidin-9-olate ligand, the another O atom of the second 3-(2-hydroxyethyl)-2-methyl-4-oxopyrido[1,2-a]pyrimidin-9-olate ligand, together with one water molecule and one Cl atom (Fig. 1). The bond lengths and angles are shown in Table 1. In the crystal structure, the intermolecular O—H···O hydrogen bonds connect the molecules of (I) into a two-dimensional layer along the [010] axis, Fig. 2. Two neighboring net framework layers are interconnected through intermolecular C—H···Cl, O—H···Cl hydrogen bonds forming a three-dimensionnal framework along the [100] axis, Fig. 3, Table 2.

Related literature top

For related literature, see: Bayot et al. (2006); Chen et al. (2007); Sun et al. (2008); Wu et al. (2006).

Experimental top

All chemicals used (reagent grade) were commercially available. a aqueous solution (5 ml) of CuCl₂ (28 mg, 0.1 mmol) was added with constant stirring to a ethanol solution (10 ml) containing 3-(2-hydroxyethyl)-2-methyl-9-hydroxylpyrido[1,2-a] pyrimidin-4-one (22 mg, 0.1 mmol) then filtered off. After a few days, colorless well shaped single crystals in the form of prisms deposited in the other liquid. They were separated off, washed with cold ethanol and dried in air at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme and all hydrogen atoms. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Two-dimensional net framework of the title compound viewed along b axis. Hydrogen bonds are shown as dashed lines. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. Three-dimensional net framework of the title compound viewed along a axis. Hydrogen bonds are shown as dashed lines. Displacement ellipsoids are drawn at the 30% probability level.

Bis[µ-3-(2-hydroxyethyl)-2-methyl-4-oxo- 4H-pyrido[1,2-a]pyrimidin-9-olato- κ³N,O:O]bis[aquachloridocopper(II)] top

Crystal data top

[Cu₂(C₁₁H₁₁N₂O₂)₂Cl₂(H₂O)₂]	F(000) = 684
M_r = 672.45	D_x = 1.807 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2976 reflections
a = 9.391 (3) Å	θ = 2.5–27.5°
b = 11.322 (3) Å	µ = 1.99 mm⁻¹
c = 11.905 (4) Å	T = 293 K
β = 102.414 (18)°	Prism, colorless
V = 1236.2 (6) Å³	0.25 × 0.12 × 0.08 mm
Z = 2

Data collection top

Rigaku SCXmini diffractometer	2826 independent reflections
Radiation source: fine-focus sealed tube	2249 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
Detector resolution: 8.192 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
T_min = 0.890, T_max = 1.000	l = −15→15
12472 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.059P)² + 0.8671P] where P = (F_o² + 2F_c²)/3
2826 reflections	(Δ/σ)_max = 0.001
176 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Cu₂(C₁₁H₁₁N₂O₂)₂Cl₂(H₂O)₂]	V = 1236.2 (6) Å³
M_r = 672.45	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.391 (3) Å	µ = 1.99 mm⁻¹
b = 11.322 (3) Å	T = 293 K
c = 11.905 (4) Å	0.25 × 0.12 × 0.08 mm
β = 102.414 (18)°

Data collection top

Rigaku SCXmini diffractometer	2826 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2249 reflections with I > 2σ(I)
T_min = 0.890, T_max = 1.000	R_int = 0.056
12472 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.49 e Å⁻³
2826 reflections	Δρ_min = −0.47 e Å⁻³
176 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
Cu1	0.09275 (4)	0.92674 (4)	0.60256 (3)	0.02472 (15)
C1	0.3469 (3)	1.0520 (3)	0.5971 (3)	0.0230 (7)
C2	0.2373 (4)	1.1028 (3)	0.5076 (3)	0.0241 (7)
C3	0.2761 (4)	1.1877 (3)	0.4388 (3)	0.0315 (8)
H3A	0.2069	1.2198	0.3788	0.038*
C4	0.4213 (4)	1.2264 (3)	0.4592 (3)	0.0335 (8)
H4A	0.4474	1.2855	0.4133	0.040*
C5	0.5234 (4)	1.1795 (3)	0.5441 (3)	0.0309 (8)
H5A	0.6190	1.2067	0.5566	0.037*
C6	0.6009 (4)	1.0432 (3)	0.7013 (3)	0.0294 (8)
C7	0.5562 (4)	0.9521 (3)	0.7664 (3)	0.0284 (8)
C8	0.4116 (4)	0.9186 (3)	0.7479 (3)	0.0259 (7)
C9	0.3610 (4)	0.8284 (3)	0.8226 (3)	0.0342 (9)
H9A	0.2576	0.8176	0.7978	0.051*
H9B	0.3833	0.8550	0.9010	0.051*
H9C	0.4097	0.7548	0.8169	0.051*
C10	0.6746 (4)	0.8972 (3)	0.8572 (3)	0.0319 (8)
H10A	0.6415	0.8209	0.8786	0.038*
H10B	0.7601	0.8841	0.8254	0.038*
C11	0.7161 (5)	0.9729 (4)	0.9631 (3)	0.0421 (10)
H11A	0.7600	1.0453	0.9432	0.051*
H11B	0.6285	0.9939	0.9893	0.051*
O1	0.7242 (3)	1.0832 (2)	0.7112 (3)	0.0412 (7)
O2	0.8149 (3)	0.9165 (3)	1.0542 (3)	0.0441 (8)
O3	0.1054 (2)	1.0586 (2)	0.4999 (2)	0.0313 (6)
O5	0.0115 (3)	1.0044 (3)	0.7446 (2)	0.0542 (9)
H5C	0.0633	0.9835	0.8059	0.081*
H5D	−0.0866	0.9780	0.7408	0.081*
N1	0.3065 (3)	0.9674 (2)	0.6621 (2)	0.0244 (6)
N2	0.4871 (3)	1.0915 (2)	0.6127 (2)	0.0253 (6)
Cl1	0.07956 (10)	0.73242 (8)	0.63230 (9)	0.0408 (3)
H2A	0.775 (6)	0.878 (5)	1.088 (5)	0.07 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0176 (2)	0.0284 (2)	0.0255 (2)	−0.00189 (17)	−0.00112 (16)	0.00366 (16)
C1	0.0188 (16)	0.0241 (16)	0.0247 (17)	−0.0006 (13)	0.0013 (13)	−0.0017 (13)
C2	0.0168 (15)	0.0286 (17)	0.0260 (17)	0.0011 (13)	0.0022 (13)	−0.0013 (13)
C3	0.0283 (18)	0.0332 (19)	0.032 (2)	0.0011 (16)	0.0041 (15)	0.0050 (15)
C4	0.0291 (18)	0.032 (2)	0.040 (2)	−0.0036 (16)	0.0079 (16)	0.0057 (16)
C5	0.0222 (17)	0.0316 (19)	0.039 (2)	−0.0077 (15)	0.0074 (15)	−0.0011 (15)
C6	0.0162 (16)	0.0350 (19)	0.0337 (19)	0.0002 (14)	−0.0021 (14)	−0.0057 (15)
C7	0.0195 (16)	0.0326 (19)	0.0299 (18)	0.0024 (14)	−0.0019 (14)	−0.0050 (14)
C8	0.0214 (16)	0.0276 (17)	0.0253 (17)	0.0036 (14)	−0.0025 (13)	−0.0005 (13)
C9	0.0294 (19)	0.041 (2)	0.0278 (19)	0.0015 (16)	−0.0038 (15)	0.0064 (15)
C10	0.0212 (17)	0.035 (2)	0.035 (2)	0.0064 (15)	−0.0023 (15)	−0.0025 (15)
C11	0.037 (2)	0.041 (2)	0.040 (2)	0.0059 (18)	−0.0092 (17)	−0.0046 (18)
O1	0.0170 (12)	0.0495 (17)	0.0534 (18)	−0.0039 (12)	−0.0007 (12)	0.0014 (13)
O2	0.0312 (16)	0.061 (2)	0.0326 (16)	0.0038 (15)	−0.0087 (13)	0.0010 (14)
O3	0.0160 (11)	0.0413 (15)	0.0321 (14)	−0.0044 (10)	−0.0046 (10)	0.0130 (11)
O5	0.0263 (14)	0.096 (3)	0.0377 (16)	0.0102 (17)	0.0005 (12)	−0.0210 (17)
N1	0.0200 (14)	0.0247 (14)	0.0264 (15)	0.0009 (11)	0.0005 (11)	0.0007 (11)
N2	0.0162 (13)	0.0282 (15)	0.0308 (16)	−0.0025 (11)	0.0039 (11)	−0.0015 (12)
Cl1	0.0355 (5)	0.0293 (5)	0.0518 (6)	−0.0015 (4)	−0.0037 (4)	0.0049 (4)

Geometric parameters (Å, º) top

Cu1—O3	1.949 (2)	C6—N2	1.438 (4)
Cu1—O3ⁱ	2.001 (2)	C7—C8	1.382 (5)
Cu1—N1	2.033 (3)	C7—C10	1.508 (5)
Cu1—O5	2.184 (3)	C8—N1	1.375 (4)
Cu1—Cl1	2.2361 (11)	C8—C9	1.496 (5)
Cu1—Cl1	2.2361 (11)	C9—H9A	0.9600
C1—N1	1.336 (4)	C9—H9B	0.9600
C1—N2	1.365 (4)	C9—H9C	0.9600
C1—C2	1.434 (5)	C10—C11	1.505 (5)
C2—O3	1.320 (4)	C10—H10A	0.9700
C2—C3	1.363 (5)	C10—H10B	0.9700
C3—C4	1.403 (5)	C11—O2	1.419 (5)
C3—H3A	0.9300	C11—H11A	0.9700
C4—C5	1.344 (5)	C11—H11B	0.9700
C4—H4A	0.9300	O2—H2A	0.75 (6)
C5—N2	1.377 (4)	O3—Cu1ⁱ	2.001 (2)
C5—H5A	0.9300	O5—H5C	0.8200
C6—O1	1.225 (4)	O5—H5D	0.9599
C6—C7	1.407 (5)	Cl1—Cl1	0.000 (3)

O3—Cu1—O3ⁱ	74.24 (11)	N1—C8—C7	122.1 (3)
O3—Cu1—N1	81.74 (10)	N1—C8—C9	116.6 (3)
O3ⁱ—Cu1—N1	155.95 (11)	C7—C8—C9	121.3 (3)
O3—Cu1—O5	104.82 (13)	C8—C9—H9A	109.5
O3ⁱ—Cu1—O5	90.24 (11)	C8—C9—H9B	109.5
N1—Cu1—O5	97.00 (11)	H9A—C9—H9B	109.5
O3—Cu1—Cl1	149.96 (9)	C8—C9—H9C	109.5
O3ⁱ—Cu1—Cl1	95.88 (7)	H9A—C9—H9C	109.5
N1—Cu1—Cl1	104.60 (8)	H9B—C9—H9C	109.5
O5—Cu1—Cl1	103.49 (10)	C11—C10—C7	112.6 (3)
O3—Cu1—Cl1	149.96 (9)	C11—C10—H10A	109.1
O3ⁱ—Cu1—Cl1	95.88 (7)	C7—C10—H10A	109.1
N1—Cu1—Cl1	104.60 (8)	C11—C10—H10B	109.1
O5—Cu1—Cl1	103.49 (10)	C7—C10—H10B	109.1
Cl1—Cu1—Cl1	0.00 (7)	H10A—C10—H10B	107.8
N1—C1—N2	122.8 (3)	O2—C11—C10	113.2 (3)
N1—C1—C2	118.1 (3)	O2—C11—H11A	108.9
N2—C1—C2	119.1 (3)	C10—C11—H11A	108.9
O3—C2—C3	126.4 (3)	O2—C11—H11B	108.9
O3—C2—C1	114.4 (3)	C10—C11—H11B	108.9
C3—C2—C1	119.2 (3)	H11A—C11—H11B	107.8
C2—C3—C4	119.5 (3)	C11—O2—H2A	111 (5)
C2—C3—H3A	120.3	C2—O3—Cu1	115.4 (2)
C4—C3—H3A	120.3	C2—O3—Cu1ⁱ	138.3 (2)
C5—C4—C3	121.1 (3)	Cu1—O3—Cu1ⁱ	105.76 (11)
C5—C4—H4A	119.4	Cu1—O5—H5C	109.5
C3—C4—H4A	119.4	Cu1—O5—H5D	109.3
C4—C5—N2	120.3 (3)	H5C—O5—H5D	109.3
C4—C5—H5A	119.8	C1—N1—C8	118.1 (3)
N2—C5—H5A	119.8	C1—N1—Cu1	110.0 (2)
O1—C6—C7	127.3 (3)	C8—N1—Cu1	131.7 (2)
O1—C6—N2	117.9 (3)	C1—N2—C5	120.7 (3)
C7—C6—N2	114.8 (3)	C1—N2—C6	121.2 (3)
C8—C7—C6	120.9 (3)	C5—N2—C6	118.1 (3)
C8—C7—C10	123.3 (3)	Cl1—Cl1—Cu1	0 (10)
C6—C7—C10	115.9 (3)

N1—C1—C2—O3	−0.1 (5)	N2—C1—N1—C8	−0.2 (5)
N2—C1—C2—O3	−179.9 (3)	C2—C1—N1—C8	180.0 (3)
N1—C1—C2—C3	−178.9 (3)	N2—C1—N1—Cu1	−175.7 (3)
N2—C1—C2—C3	1.2 (5)	C2—C1—N1—Cu1	4.4 (4)
O3—C2—C3—C4	179.3 (3)	C7—C8—N1—C1	−1.7 (5)
C1—C2—C3—C4	−2.1 (5)	C9—C8—N1—C1	177.1 (3)
C2—C3—C4—C5	1.3 (6)	C7—C8—N1—Cu1	172.7 (3)
C3—C4—C5—N2	0.4 (6)	C9—C8—N1—Cu1	−8.5 (5)
O1—C6—C7—C8	177.8 (4)	O3—Cu1—N1—C1	−5.3 (2)
N2—C6—C7—C8	−3.3 (5)	O3ⁱ—Cu1—N1—C1	−2.7 (4)
O1—C6—C7—C10	−0.8 (6)	O5—Cu1—N1—C1	−109.3 (2)
N2—C6—C7—C10	178.0 (3)	Cl1—Cu1—N1—C1	144.7 (2)
C6—C7—C8—N1	3.5 (5)	Cl1—Cu1—N1—C1	144.7 (2)
C10—C7—C8—N1	−177.9 (3)	O3—Cu1—N1—C8	−180.0 (3)
C6—C7—C8—C9	−175.2 (3)	O3ⁱ—Cu1—N1—C8	−177.5 (3)
C10—C7—C8—C9	3.4 (5)	O5—Cu1—N1—C8	76.0 (3)
C8—C7—C10—C11	−101.0 (4)	Cl1—Cu1—N1—C8	−30.0 (3)
C6—C7—C10—C11	77.6 (4)	Cl1—Cu1—N1—C8	−30.0 (3)
C7—C10—C11—O2	173.1 (3)	N1—C1—N2—C5	−179.5 (3)
C3—C2—O3—Cu1	174.0 (3)	C2—C1—N2—C5	0.4 (5)
C1—C2—O3—Cu1	−4.7 (4)	N1—C1—N2—C6	0.1 (5)
C3—C2—O3—Cu1ⁱ	3.6 (6)	C2—C1—N2—C6	180.0 (3)
C1—C2—O3—Cu1ⁱ	−175.1 (2)	C4—C5—N2—C1	−1.2 (5)
O3ⁱ—Cu1—O3—C2	−173.4 (3)	C4—C5—N2—C6	179.2 (3)
N1—Cu1—O3—C2	5.6 (2)	O1—C6—N2—C1	−179.5 (3)
O5—Cu1—O3—C2	100.7 (2)	C7—C6—N2—C1	1.6 (5)
Cl1—Cu1—O3—C2	−99.4 (3)	O1—C6—N2—C5	0.1 (5)
Cl1—Cu1—O3—C2	−99.4 (3)	C7—C6—N2—C5	−178.8 (3)
O3ⁱ—Cu1—O3—Cu1ⁱ	0.0	O3—Cu1—Cl1—Cl1	0.0 (5)
N1—Cu1—O3—Cu1ⁱ	178.93 (14)	O3ⁱ—Cu1—Cl1—Cl1	0.0 (5)
O5—Cu1—O3—Cu1ⁱ	−85.97 (13)	N1—Cu1—Cl1—Cl1	0.0 (5)
Cl1—Cu1—O3—Cu1ⁱ	74.01 (18)	O5—Cu1—Cl1—Cl1	0.0 (5)
Cl1—Cu1—O3—Cu1ⁱ	74.01 (18)

Symmetry code: (i) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5C···O2ⁱⁱ	0.82	2.13	2.742 (4)	131
O5—H5D···O1ⁱⁱⁱ	0.96	2.11	2.788 (4)	127
O2—H2A···Cl1^iv	0.75 (6)	2.37 (6)	3.078 (4)	158 (6)
C9—H9A···Cl1	0.96	2.49	3.275 (4)	139
C3—H3A···Cl1ⁱ	0.93	2.72	3.387 (4)	130

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₁H₁₁N₂O₂)₂Cl₂(H₂O)₂]
M_r	672.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.391 (3), 11.322 (3), 11.905 (4)
β (°)	102.414 (18)
V (Å³)	1236.2 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.99
Crystal size (mm)	0.25 × 0.12 × 0.08

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.890, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12472, 2826, 2249
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.115, 1.02
No. of reflections	2826
No. of parameters	176
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.47

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5C···O2ⁱ	0.82	2.13	2.742 (4)	131.1
O5—H5D···O1ⁱⁱ	0.96	2.11	2.788 (4)	126.7
O2—H2A···Cl1ⁱⁱⁱ	0.75 (6)	2.37 (6)	3.078 (4)	158 (6)
C9—H9A···Cl1	0.96	2.49	3.275 (4)	139.1
C3—H3A···Cl1^iv	0.93	2.72	3.387 (4)	129.5

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

References

Bayot, D., Degand, M., Tinant, B. & Devillers, M. (2006). Inorg. Chem. Commun. 359, 1390–1394. CAS Google Scholar
Chen, K., Zhang, Y.-L., Feng, M.-Q. & Liu, C.-H. (2007). Acta Cryst. E63, m2033. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, Y., Jiang, X.-D. & Li, X.-B. (2008). Acta Cryst. E64, m801. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wu, H., Dong, X.-W., Liu, H.-Y. & Ma, J.-F. (2006). Acta Cryst. E62, m281–m282. Web of Science CSD CrossRef IUCr Journals Google Scholar

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