Bis(2,2′-bipyrid­yl)(dichloro­acetato)copper(II) dichloro­acetate dihydrate

Li, Y.-F.; Wang, L.-T.; Jian, F.-F.

doi:10.1107/S1600536809055640

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page m141

https://doi.org/10.1107/S1600536809055640

Open

access

Bis(2,2′-bipyridyl)(dichloroacetato)copper(II) dichloroacetate dihydrate

Yu-Feng Li,^a Lin-Tong Wang ^b and Fang-Fang Jian ^c ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, ^bDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^cMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 25 December 2009; accepted 29 December 2009; online 13 January 2010)

In the title compound, [Cu(C₂HCl₂O₂)(C₁₀H₈N₂)₂](C₂HCl₂O₂)·2H₂O, the Cu^II ion is bonded to two N,N′-bidentate 2,2′-bipyridyl ligands and one O-monodentate 2,2-dichloroacetate anion in a distorted CuON₄ trigonal-bipyramidal geometry, with the O atom occupying an equatorial site. In the crystal, the components are linked by O—H⋯O and O—H⋯Cl hydrogen bonds.

Related literature

For a related structure, see: Barszcz et al. (2004 ).

Experimental

Crystal data

[Cu(C₂HCl₂O₂)(C₁₀H₈N₂)₂](C₂HCl₂O₂)·2H₂O
M_r = 667.80
Triclinic, $[P \overline 1]$
a = 9.9710 (7) Å
b = 11.7307 (9) Å
c = 12.4736 (9) Å
α = 105.407 (1)°
β = 101.499 (1)°
γ = 95.513 (1)°
V = 1361.07 (17) Å³
Z = 2
Mo Kα radiation
μ = 1.24 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
7789 measured reflections
5280 independent reflections
4592 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.097
S = 1.06
5280 reflections
365 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—N1	1.9879 (18)
Cu1—N4	1.9889 (18)
Cu1—O1	2.0121 (16)
Cu1—N3	2.0711 (18)
Cu1—N2	2.1201 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯Cl2	0.84 (2)	2.79 (2)	3.571 (3)	155 (4)
O1W—H1B⋯O4	0.86 (2)	1.93 (2)	2.787 (4)	171 (4)
O2W—H2A⋯Cl1	0.88 (2)	2.76 (2)	3.511 (3)	144 (3)
O2W—H2B⋯O3ⁱ	0.87 (2)	1.89 (2)	2.757 (3)	172 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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 global, I. DOI: https://doi.org/10.1107/S1600536809055640/hb5295sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055640/hb5295Isup2.hkl

checkCIF report

Related literature top

For a related structure, see: Barszcz et al. (2004).

Experimental top

Copper(II) 2,2-dicholoracetate, 0.32 g (1 mmol) and 2,2'-bipyridine 0.31 g (2 mmol) were added to 65 ml anhydrous alcohol under stirring. The mixture was refluxed for 7 h. The blue solution was filtered and the filtrate was left to stand undisturbed. Upon slow evaporation at room temperature, blue blocks of (I) appeared three days later and were separated by filtration.

Structure description top

For a related structure, see: Barszcz et al. (2004).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 for (I), with displacement ellipsoids drawn at the 30% probability level.

Bis(2,2'-bipyridyl)(dichloroacetato)copper(II) dichloroacetate dihydrate top

Crystal data top

[Cu(C₂HCl₂O₂)(C₁₀H₈N₂)₂](C₂HCl₂O₂)·2H₂O	Z = 2
M_r = 667.80	F(000) = 678
Triclinic, P1	D_x = 1.629 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9710 (7) Å	Cell parameters from 2240 reflections
b = 11.7307 (9) Å	θ = 2.2–28.3°
c = 12.4736 (9) Å	µ = 1.24 mm⁻¹
α = 105.407 (1)°	T = 293 K
β = 101.499 (1)°	Block, blue
γ = 95.513 (1)°	0.22 × 0.20 × 0.18 mm
V = 1361.07 (17) Å³

Data collection top

Bruker SMART CCD diffractometer	4592 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 26.0°, θ_min = 1.8°
phi and ω scans	h = −11→12
7789 measured reflections	k = −13→14
5280 independent reflections	l = −15→14

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0542P)² + 0.3598P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
5280 reflections	Δρ_max = 0.65 e Å⁻³
365 parameters	Δρ_min = −0.64 e Å⁻³
7 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0256 (15)

Crystal data top

[Cu(C₂HCl₂O₂)(C₁₀H₈N₂)₂](C₂HCl₂O₂)·2H₂O	γ = 95.513 (1)°
M_r = 667.80	V = 1361.07 (17) Å³
Triclinic, P1	Z = 2
a = 9.9710 (7) Å	Mo Kα radiation
b = 11.7307 (9) Å	µ = 1.24 mm⁻¹
c = 12.4736 (9) Å	T = 293 K
α = 105.407 (1)°	0.22 × 0.20 × 0.18 mm
β = 101.499 (1)°

Data collection top

Bruker SMART CCD diffractometer	4592 reflections with I > 2σ(I)
7789 measured reflections	R_int = 0.033
5280 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	7 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.65 e Å⁻³
5280 reflections	Δρ_min = −0.64 e Å⁻³
365 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	0.02070 (3)	0.28505 (2)	0.24318 (2)	0.03074 (11)
Cl1	0.45242 (8)	0.39464 (9)	0.06435 (8)	0.0741 (3)
Cl2	0.50350 (6)	0.30032 (6)	0.25678 (6)	0.04867 (17)
O1	0.21727 (16)	0.36582 (14)	0.27220 (14)	0.0396 (4)
O2	0.17501 (17)	0.31459 (16)	0.08196 (15)	0.0459 (4)
N1	−0.06224 (19)	0.43199 (16)	0.24029 (15)	0.0318 (4)
N2	−0.05985 (19)	0.31277 (16)	0.39146 (15)	0.0326 (4)
N3	−0.13923 (19)	0.17107 (16)	0.11654 (15)	0.0328 (4)
N4	0.08416 (19)	0.12907 (17)	0.24147 (16)	0.0347 (4)
C1	−0.0573 (3)	0.4885 (2)	0.1606 (2)	0.0406 (5)
H1	−0.0007	0.4659	0.1103	0.049*
C2	−0.1329 (3)	0.5790 (2)	0.1503 (2)	0.0465 (6)
H2	−0.1280	0.6162	0.0936	0.056*
C3	−0.2157 (3)	0.6134 (2)	0.2255 (2)	0.0467 (6)
H3	−0.2691	0.6732	0.2193	0.056*
C4	−0.2185 (2)	0.5581 (2)	0.3104 (2)	0.0415 (5)
H4	−0.2722	0.5816	0.3629	0.050*
C5	−0.1403 (2)	0.46721 (18)	0.31641 (18)	0.0303 (4)
C6	−0.1365 (2)	0.40123 (18)	0.40308 (17)	0.0299 (4)
C7	−0.2055 (2)	0.4282 (2)	0.4908 (2)	0.0404 (5)
H6	−0.2572	0.4905	0.4982	0.049*
C8	−0.1960 (3)	0.3608 (2)	0.5670 (2)	0.0460 (6)
H8	−0.2415	0.3771	0.6263	0.055*
C9	−0.1187 (3)	0.2699 (2)	0.5541 (2)	0.0472 (6)
H9	−0.1114	0.2233	0.6041	0.057*
C10	−0.0515 (3)	0.2483 (2)	0.4653 (2)	0.0411 (5)
H10	0.0013	0.1868	0.4569	0.049*
C11	−0.2514 (2)	0.1998 (2)	0.0568 (2)	0.0405 (5)
H11	−0.2605	0.2802	0.0702	0.049*
C12	−0.3538 (3)	0.1155 (3)	−0.0237 (2)	0.0495 (6)
H12	−0.4300	0.1383	−0.0644	0.059*
C13	−0.3404 (3)	−0.0027 (3)	−0.0422 (2)	0.0525 (7)
H13	−0.4082	−0.0614	−0.0960	0.063*
C14	−0.2268 (3)	−0.0348 (2)	0.0188 (2)	0.0457 (6)
H14	−0.2175	−0.1150	0.0072	0.055*
C15	−0.1260 (2)	0.05451 (19)	0.09785 (18)	0.0334 (5)
C16	0.0007 (2)	0.0309 (2)	0.16703 (19)	0.0351 (5)
C17	0.0356 (3)	−0.0829 (2)	0.1571 (2)	0.0478 (6)
H17	−0.0222	−0.1500	0.1051	0.057*
C18	0.1576 (3)	−0.0946 (3)	0.2256 (3)	0.0571 (8)
H18	0.1831	−0.1698	0.2199	0.069*
C19	0.2412 (3)	0.0060 (3)	0.3024 (2)	0.0528 (7)
H19	0.3232	−0.0005	0.3495	0.063*
C20	0.2015 (3)	0.1165 (2)	0.3086 (2)	0.0450 (6)
H20	0.2577	0.1843	0.3607	0.054*
C21	0.2517 (2)	0.35388 (19)	0.1777 (2)	0.0341 (5)
C22	0.4076 (2)	0.3961 (2)	0.1938 (2)	0.0402 (5)
H22	0.4324	0.4778	0.2456	0.048*
Cl3	0.17481 (9)	0.06640 (8)	0.59492 (10)	0.0833 (3)
Cl4	0.36379 (9)	−0.04850 (8)	0.72163 (7)	0.0722 (2)
O3	0.4801 (3)	0.2075 (2)	0.7501 (2)	0.0807 (7)
O4	0.4943 (3)	0.1598 (2)	0.5687 (3)	0.0971 (9)
C23	0.3436 (3)	0.0293 (2)	0.6185 (2)	0.0466 (6)
H23A	0.3545	−0.0240	0.5466	0.056*
C24	0.4501 (3)	0.1442 (3)	0.6506 (3)	0.0550 (7)
O1W	0.4574 (3)	0.3842 (2)	0.5424 (2)	0.0744 (7)
H1A	0.455 (4)	0.384 (4)	0.4747 (19)	0.089*
H1B	0.467 (4)	0.312 (2)	0.543 (3)	0.089*
O2W	0.2759 (3)	0.6333 (2)	0.1579 (3)	0.0885 (8)
H2A	0.299 (3)	0.579 (2)	0.104 (2)	0.106*
H2B	0.349 (3)	0.686 (3)	0.192 (3)	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03054 (16)	0.02735 (16)	0.03555 (17)	0.00635 (10)	0.00873 (11)	0.00987 (11)
Cl1	0.0572 (4)	0.1167 (7)	0.0791 (5)	0.0245 (5)	0.0366 (4)	0.0615 (5)
Cl2	0.0370 (3)	0.0532 (4)	0.0565 (4)	0.0097 (3)	0.0046 (3)	0.0210 (3)
O1	0.0362 (8)	0.0390 (9)	0.0408 (9)	0.0010 (7)	0.0126 (7)	0.0062 (7)
O2	0.0399 (9)	0.0490 (10)	0.0437 (10)	0.0044 (8)	0.0057 (8)	0.0091 (8)
N1	0.0333 (9)	0.0273 (9)	0.0355 (9)	0.0062 (7)	0.0103 (8)	0.0083 (7)
N2	0.0341 (9)	0.0306 (9)	0.0314 (9)	0.0031 (7)	0.0070 (8)	0.0073 (7)
N3	0.0332 (9)	0.0300 (9)	0.0337 (9)	0.0034 (7)	0.0085 (8)	0.0070 (7)
N4	0.0354 (10)	0.0352 (10)	0.0375 (10)	0.0100 (8)	0.0118 (8)	0.0130 (8)
C1	0.0478 (14)	0.0352 (12)	0.0423 (13)	0.0085 (10)	0.0143 (11)	0.0140 (10)
C2	0.0562 (16)	0.0365 (13)	0.0501 (14)	0.0084 (11)	0.0097 (12)	0.0199 (11)
C3	0.0469 (14)	0.0349 (13)	0.0582 (16)	0.0147 (11)	0.0073 (12)	0.0140 (11)
C4	0.0384 (12)	0.0368 (13)	0.0480 (14)	0.0108 (10)	0.0112 (11)	0.0076 (10)
C5	0.0250 (10)	0.0268 (10)	0.0339 (11)	−0.0008 (8)	0.0038 (8)	0.0040 (8)
C6	0.0251 (10)	0.0287 (10)	0.0300 (10)	−0.0027 (8)	0.0036 (8)	0.0031 (8)
C7	0.0343 (12)	0.0429 (13)	0.0396 (12)	0.0027 (10)	0.0116 (10)	0.0034 (10)
C8	0.0433 (14)	0.0579 (16)	0.0347 (12)	−0.0009 (12)	0.0162 (11)	0.0078 (11)
C9	0.0540 (15)	0.0526 (15)	0.0374 (13)	−0.0002 (12)	0.0121 (11)	0.0191 (11)
C10	0.0464 (14)	0.0402 (13)	0.0401 (13)	0.0074 (10)	0.0115 (11)	0.0160 (10)
C11	0.0361 (12)	0.0399 (13)	0.0423 (13)	0.0057 (10)	0.0047 (10)	0.0100 (10)
C12	0.0372 (13)	0.0603 (17)	0.0445 (14)	0.0023 (12)	0.0023 (11)	0.0119 (12)
C13	0.0465 (15)	0.0520 (16)	0.0445 (14)	−0.0091 (12)	0.0039 (12)	0.0008 (12)
C14	0.0526 (15)	0.0332 (12)	0.0450 (14)	−0.0018 (11)	0.0142 (12)	0.0018 (10)
C15	0.0377 (12)	0.0306 (11)	0.0328 (11)	0.0034 (9)	0.0149 (9)	0.0068 (9)
C16	0.0426 (12)	0.0314 (11)	0.0382 (12)	0.0084 (10)	0.0209 (10)	0.0123 (9)
C17	0.0645 (17)	0.0339 (13)	0.0553 (15)	0.0157 (12)	0.0273 (13)	0.0179 (11)
C18	0.081 (2)	0.0492 (16)	0.0656 (18)	0.0368 (15)	0.0391 (17)	0.0323 (14)
C19	0.0521 (16)	0.0683 (19)	0.0564 (16)	0.0319 (14)	0.0212 (13)	0.0349 (15)
C20	0.0412 (13)	0.0545 (15)	0.0449 (13)	0.0157 (12)	0.0108 (11)	0.0207 (12)
C21	0.0345 (11)	0.0244 (10)	0.0450 (13)	0.0052 (9)	0.0116 (10)	0.0110 (9)
C22	0.0361 (12)	0.0368 (12)	0.0500 (14)	0.0044 (10)	0.0134 (11)	0.0148 (11)
Cl3	0.0527 (4)	0.0712 (5)	0.1169 (8)	0.0183 (4)	−0.0088 (5)	0.0304 (5)
Cl4	0.0675 (5)	0.0819 (6)	0.0722 (5)	0.0014 (4)	−0.0030 (4)	0.0485 (4)
O3	0.0808 (17)	0.0708 (16)	0.0752 (16)	−0.0105 (13)	0.0049 (13)	0.0133 (13)
O4	0.139 (3)	0.0615 (15)	0.108 (2)	0.0046 (15)	0.068 (2)	0.0287 (14)
C23	0.0518 (15)	0.0491 (15)	0.0428 (13)	0.0156 (12)	0.0092 (12)	0.0187 (11)
C24	0.0577 (17)	0.0466 (16)	0.0661 (19)	0.0142 (13)	0.0198 (15)	0.0196 (14)
O1W	0.0842 (16)	0.0731 (16)	0.0853 (17)	0.0306 (13)	0.0462 (15)	0.0298 (14)
O2W	0.0756 (17)	0.0565 (15)	0.130 (2)	0.0066 (12)	0.0219 (17)	0.0243 (15)

Geometric parameters (Å, º) top

Cu1—N1	1.9879 (18)	C9—H9	0.9300
Cu1—N4	1.9889 (18)	C10—H10	0.9300
Cu1—O1	2.0121 (16)	C11—C12	1.378 (3)
Cu1—N3	2.0711 (18)	C11—H11	0.9300
Cu1—N2	2.1201 (18)	C12—C13	1.368 (4)
Cl1—C22	1.755 (3)	C12—H12	0.9300
Cl2—C22	1.780 (2)	C13—C14	1.377 (4)
O1—C21	1.268 (3)	C13—H13	0.9300
O2—C21	1.225 (3)	C14—C15	1.390 (3)
N1—C1	1.340 (3)	C14—H14	0.9300
N1—C5	1.352 (3)	C15—C16	1.476 (3)
N2—C10	1.333 (3)	C16—C17	1.391 (3)
N2—C6	1.341 (3)	C17—C18	1.382 (4)
N3—C11	1.339 (3)	C17—H17	0.9300
N3—C15	1.349 (3)	C18—C19	1.377 (4)
N4—C20	1.341 (3)	C18—H18	0.9300
N4—C16	1.350 (3)	C19—C20	1.379 (4)
C1—C2	1.378 (3)	C19—H19	0.9300
C1—H1	0.9300	C20—H20	0.9300
C2—C3	1.377 (4)	C21—C22	1.542 (3)
C2—H2	0.9300	C22—H22	0.9800
C3—C4	1.385 (4)	Cl3—C23	1.766 (3)
C3—H3	0.9300	Cl4—C23	1.757 (3)
C4—C5	1.388 (3)	O3—C24	1.225 (4)
C4—H4	0.9300	O4—C24	1.239 (4)
C5—C6	1.484 (3)	C23—C24	1.540 (4)
C6—C7	1.388 (3)	C23—H23A	0.9800
C7—C8	1.384 (4)	O1W—H1A	0.839 (18)
C7—H6	0.9300	O1W—H1B	0.861 (19)
C8—C9	1.369 (4)	O2W—H2A	0.884 (16)
C8—H8	0.9300	O2W—H2B	0.867 (18)
C9—C10	1.385 (3)

N1—Cu1—N4	174.19 (8)	C9—C10—H10	118.8
N1—Cu1—O1	94.77 (7)	N3—C11—C12	122.9 (2)
N4—Cu1—O1	91.01 (7)	N3—C11—H11	118.5
N1—Cu1—N3	94.63 (7)	C12—C11—H11	118.5
N4—Cu1—N3	80.37 (7)	C13—C12—C11	118.3 (3)
O1—Cu1—N3	142.56 (7)	C13—C12—H12	120.9
N1—Cu1—N2	79.44 (7)	C11—C12—H12	120.9
N4—Cu1—N2	98.73 (7)	C12—C13—C14	120.0 (2)
O1—Cu1—N2	114.17 (7)	C12—C13—H13	120.0
N3—Cu1—N2	103.17 (7)	C14—C13—H13	120.0
C21—O1—Cu1	109.56 (14)	C13—C14—C15	119.0 (2)
C1—N1—C5	119.18 (19)	C13—C14—H14	120.5
C1—N1—Cu1	123.79 (15)	C15—C14—H14	120.5
C5—N1—Cu1	116.62 (15)	N3—C15—C14	121.1 (2)
C10—N2—C6	118.93 (19)	N3—C15—C16	115.17 (19)
C10—N2—Cu1	127.95 (16)	C14—C15—C16	123.8 (2)
C6—N2—Cu1	112.90 (14)	N4—C16—C17	121.1 (2)
C11—N3—C15	118.69 (19)	N4—C16—C15	115.04 (19)
C11—N3—Cu1	127.97 (16)	C17—C16—C15	123.8 (2)
C15—N3—Cu1	113.30 (14)	C18—C17—C16	119.0 (3)
C20—N4—C16	119.4 (2)	C18—C17—H17	120.5
C20—N4—Cu1	124.53 (17)	C16—C17—H17	120.5
C16—N4—Cu1	116.08 (15)	C19—C18—C17	119.5 (2)
N1—C1—C2	122.5 (2)	C19—C18—H18	120.3
N1—C1—H1	118.7	C17—C18—H18	120.3
C2—C1—H1	118.7	C18—C19—C20	119.1 (3)
C3—C2—C1	118.8 (2)	C18—C19—H19	120.5
C3—C2—H2	120.6	C20—C19—H19	120.5
C1—C2—H2	120.6	N4—C20—C19	121.9 (3)
C2—C3—C4	119.2 (2)	N4—C20—H20	119.0
C2—C3—H3	120.4	C19—C20—H20	119.0
C4—C3—H3	120.4	O2—C21—O1	126.7 (2)
C3—C4—C5	119.4 (2)	O2—C21—C22	120.8 (2)
C3—C4—H4	120.3	O1—C21—C22	112.5 (2)
C5—C4—H4	120.3	C21—C22—Cl1	112.61 (17)
N1—C5—C4	120.8 (2)	C21—C22—Cl2	108.80 (16)
N1—C5—C6	115.24 (18)	Cl1—C22—Cl2	108.94 (13)
C4—C5—C6	123.9 (2)	C21—C22—H22	108.8
N2—C6—C7	121.7 (2)	Cl1—C22—H22	108.8
N2—C6—C5	114.97 (18)	Cl2—C22—H22	108.8
C7—C6—C5	123.4 (2)	C24—C23—Cl4	113.67 (19)
C8—C7—C6	118.9 (2)	C24—C23—Cl3	109.08 (18)
C8—C7—H6	120.6	Cl4—C23—Cl3	109.69 (15)
C6—C7—H6	120.6	C24—C23—H23A	108.1
C9—C8—C7	119.2 (2)	Cl4—C23—H23A	108.1
C9—C8—H8	120.4	Cl3—C23—H23A	108.1
C7—C8—H8	120.4	O3—C24—O4	128.5 (3)
C8—C9—C10	119.0 (2)	O3—C24—C23	118.1 (3)
C8—C9—H9	120.5	O4—C24—C23	113.4 (3)
C10—C9—H9	120.5	H1A—O1W—H1B	104 (4)
N2—C10—C9	122.3 (2)	H2A—O2W—H2B	107 (2)
N2—C10—H10	118.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···Cl2	0.84 (2)	2.79 (2)	3.571 (3)	155 (4)
O1W—H1B···O4	0.86 (2)	1.93 (2)	2.787 (4)	171 (4)
O2W—H2A···Cl1	0.88 (2)	2.76 (2)	3.511 (3)	144 (3)
O2W—H2B···O3ⁱ	0.87 (2)	1.89 (2)	2.757 (3)	172 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₂HCl₂O₂)(C₁₀H₈N₂)₂](C₂HCl₂O₂)·2H₂O
M_r	667.80
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.9710 (7), 11.7307 (9), 12.4736 (9)
α, β, γ (°)	105.407 (1), 101.499 (1), 95.513 (1)
V (Å³)	1361.07 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.24
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7789, 5280, 4592
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.097, 1.06
No. of reflections	5280
No. of parameters	365
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.64

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—N1	1.9879 (18)	Cu1—N3	2.0711 (18)
Cu1—N4	1.9889 (18)	Cu1—N2	2.1201 (18)
Cu1—O1	2.0121 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···Cl2	0.839 (18)	2.79 (2)	3.571 (3)	155 (4)
O1W—H1B···O4	0.861 (19)	1.93 (2)	2.787 (4)	171 (4)
O2W—H2A···Cl1	0.884 (16)	2.756 (17)	3.511 (3)	144 (3)
O2W—H2B···O3ⁱ	0.867 (18)	1.89 (2)	2.757 (3)	172 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors would like to thank the Science Foundation of Weifang University (No. 2009Z24) and the Natural Science Foundation of Shandong Province (No. ZR2009BM041)

References

Barszcz, B., Glowiak, T., Jezierska, J. & Tomkiewicz, A. (2004). Polyhedron, 23, 1308–1316 Web of Science CSD CrossRef Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar