Aqua­bis(2-chloro­acetato-κO)(1,10-phenanthroline-κ2N,N′)copper(II)

Yang, R.; Li, Y.; Sun, J.; Li, J.; Chu, C.

doi:10.1107/S1600536808000044

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m348

doi:10.1107/S1600536808000044

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Aquabis(2-chloroacetato-κO)(1,10-phenanthroline-κ²N,N′)copper(II)

Rongdong Yang,^a ^* Yanfei Li,^a Junshan Sun,^a Jikun Li ^a and Changqing Chu ^a

^aDepartment of Materials Science, and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: klsz79@163.com

(Received 29 November 2007; accepted 1 January 2008; online 16 January 2008)

In the title complex, [Cu(C₂H₂ClO₂)₂(C₁₂H₈N₂)(H₂O)], the Cu^II ion is five-coordinated by two N atoms [Cu—N = 2.005 (2) and 2.029 (2) Å] from the 1,10-phenanthroline ligand, two O atoms [Cu—O = 1.943 (2)–1.966 (2) Å] from two 2-chloroacetate ligands and one water molecule [Cu—O = 2.253 (2) Å] in a distorted square-pyramidal geometry. The crystal structure exhibits intermolecular O—H⋯O hydrogen bonds, short Cl⋯Cl contacts [3.334 (1) Å] and π–π interactions [centroid–centroid distance 3.621 (11) Å].

Related literature

For related crystal structures, see: Sieroń (2007 ); Czylkowska et al. (2004 ); Chen et al. (1996 ); Overgaard et al. (2003 ).

Experimental

Crystal data

[Cu(C₂H₂ClO₂)₂(C₁₂H₈N₂)(H₂O)]
M_r = 448.73
Triclinic, $[P \overline 1]$
a = 8.7730 (6) Å
b = 9.2382 (7) Å
c = 11.4492 (8) Å
α = 96.2180 (10)°
β = 106.6760 (10)°
γ = 97.9190 (10)°
V = 869.66 (11) Å³
Z = 2
Mo Kα radiation
μ = 1.59 mm⁻¹
T = 273 (2) K
0.38 × 0.25 × 0.19 mm

Data collection

Bruker SMART CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.583, T_max = 0.752
4610 measured reflections
3057 independent reflections
2837 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.074
S = 1.00
3057 reflections
235 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H15⋯O4ⁱ	0.85	1.96	2.796 (2)	169
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000044/cv2370sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808000044/cv2370Isup2.hkl

checkCIF report

Comment top

2-Chloroacetic acid and its derivatives are often used in the synthesis of mononuclear monomeric (Sieroń, 2007; Czylkowska et al., 2004) and polymeric compounds (Chen et al., 1996; Overgaard et al., 2003). In our search for new topogical structures, we selected the copper(II) ion with 2-chloroacetic acid in the presence of 1,10-phenanthroline as a co-ligand, and obtained the title compound, (I).

In (I) (Fig. 1), Cu1 exhibits a five-coordinated square-pyramidal environment, formed by two O atoms from two carboxyl ligands (Cu1—O1 1.943 (2) Å, Cu1—O3 1.966 (2) Å), one water molecule (Cu1—O5 2.243 (5) Å) and two N atoms (Cu1—N1 2.029 (2) Å, Cu1—N2 2.005 (2) Å) from 1,10-phenanthroline ligand.

In the crystal structure, there exist short intermolecular Cl···Cl contacts (Table 1), π···π stacking interactions between the aromatic rings from neighbouring molecules (Table 1), and intermolecular O—H···O hydrogen bonds (Table 2), which link the molecules into centrosymmetric dimers.

Related literature top

For related crystal structures, see: Sieroń (2007); Czylkowska et al. (2004); Chen et al. (1996); Overgaard et al. (2003).

Experimental top

The reaction was carried out by the solvothermal method. 2-Chloroacetic acid (0.188 g, 2 mmol) and cupric acetate (0.199 g, 1 mmol) and 1,10-phenanthroline (0.180 g, 1 mmol) were added to the airtight vessel with 20 ml water. The resulting green solution was filtered. The filtrate was placed for sevaral days yielding blue block-shaped crystals.

The yield is 81% and elemental analysis: calc. for C₁₆H₁₄Cl₂CuN₂O₅: C 42.82, H 3.14, N 6.24; found: C 42.55, H 3.39, N 6.32. The elemental analyses were performed with PERKIN ELMER MODEL 2400 SERIES II.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL(Sheldrick, 1997.

Figures top

Fig. 1. The molecular structure of (I) with atomic numbering and 30% probability displacement ellipsoids.

Aquabis(2-chloroacetato-κO)(1,10-phenanthroline-κ²N,N')copper(II) top

Crystal data top

[Cu(C₂H₂ClO₂)₂(C₁₂H₈N₂)(H₂O)]	Z = 2
M_r = 448.73	F(000) = 454
Triclinic, P1	D_x = 1.714 Mg m⁻³
a = 8.7730 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2382 (7) Å	Cell parameters from 3430 reflections
c = 11.4492 (8) Å	θ = 2.5–28.2°
α = 96.218 (1)°	µ = 1.59 mm⁻¹
β = 106.676 (1)°	T = 273 K
γ = 97.919 (1)°	Block, blue
V = 869.66 (11) Å³	0.38 × 0.25 × 0.19 mm

Data collection top

Bruker SMART CCD area detector diffractometer	3057 independent reflections
Radiation source: fine-focus sealed tube	2837 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
phi and ω scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.583, T_max = 0.752	k = −8→10
4610 measured reflections	l = −13→13

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.043P)² + 0.4807P] where P = (F_o² + 2F_c²)/3
3057 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.30 e Å⁻³
3 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Cu(C₂H₂ClO₂)₂(C₁₂H₈N₂)(H₂O)]	γ = 97.919 (1)°
M_r = 448.73	V = 869.66 (11) Å³
Triclinic, P1	Z = 2
a = 8.7730 (6) Å	Mo Kα radiation
b = 9.2382 (7) Å	µ = 1.59 mm⁻¹
c = 11.4492 (8) Å	T = 273 K
α = 96.218 (1)°	0.38 × 0.25 × 0.19 mm
β = 106.676 (1)°

Data collection top

Bruker SMART CCD area detector diffractometer	3057 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2837 reflections with I > 2σ(I)
T_min = 0.583, T_max = 0.752	R_int = 0.015
4610 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	3 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.00	Δρ_max = 0.30 e Å⁻³
3057 reflections	Δρ_min = −0.29 e Å⁻³
235 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	0.23816 (3)	0.68495 (3)	0.71095 (2)	0.03304 (10)
Cl1	−0.22927 (8)	0.98116 (9)	0.83337 (8)	0.0671 (2)
Cl2	0.40479 (7)	0.93989 (7)	0.62804 (6)	0.04661 (16)
O1	0.14841 (19)	0.84228 (17)	0.77963 (15)	0.0421 (4)
O2	−0.1084 (2)	0.7271 (2)	0.7366 (2)	0.0635 (5)
O3	0.11593 (19)	0.68927 (16)	0.53849 (14)	0.0408 (4)
O4	0.0053 (2)	0.7855 (2)	0.37496 (17)	0.0622 (5)
O5	0.06637 (19)	0.50494 (17)	0.74928 (15)	0.0430 (4)
H15	0.0312	0.4180	0.7091	0.052*
H16	−0.0123	0.5517	0.7385	0.052*
N1	0.4251 (2)	0.70913 (19)	0.86886 (16)	0.0328 (4)
N2	0.3550 (2)	0.53104 (19)	0.65745 (16)	0.0334 (4)
C1	0.0003 (3)	0.8353 (2)	0.77567 (19)	0.0365 (5)
C2	−0.0300 (3)	0.9841 (3)	0.8242 (2)	0.0400 (5)
H2A	−0.0099	1.0543	0.7708	0.048*
H2B	0.0464	1.0189	0.9057	0.048*
C3	0.1023 (3)	0.7947 (2)	0.4784 (2)	0.0366 (5)
C4	0.2075 (3)	0.9464 (3)	0.5315 (2)	0.0488 (6)
H4A	0.1539	1.0031	0.5788	0.059*
H4B	0.2171	0.9981	0.4639	0.059*
C5	0.4552 (3)	0.7987 (3)	0.9743 (2)	0.0404 (5)
H5A	0.3851	0.8640	0.9805	0.049*
C6	0.5887 (3)	0.7988 (3)	1.0767 (2)	0.0486 (6)
H6	0.6071	0.8642	1.1490	0.058*
C7	0.6915 (3)	0.7028 (3)	1.0699 (2)	0.0469 (6)
H7	0.7797	0.7014	1.1380	0.056*
C8	0.6639 (3)	0.6057 (3)	0.9596 (2)	0.0388 (5)
C9	0.7622 (3)	0.4983 (3)	0.9421 (2)	0.0479 (6)
H9	0.8521	0.4911	1.0067	0.057*
C10	0.7268 (3)	0.4079 (3)	0.8339 (3)	0.0477 (6)
H10	0.7934	0.3401	0.8249	0.057*
C11	0.5883 (3)	0.4140 (2)	0.7322 (2)	0.0387 (5)
C12	0.5395 (3)	0.3200 (3)	0.6177 (2)	0.0453 (6)
H12	0.6011	0.2500	0.6028	0.054*
C13	0.4019 (3)	0.3317 (3)	0.5290 (2)	0.0460 (6)
H13	0.3688	0.2690	0.4537	0.055*
C14	0.3111 (3)	0.4378 (2)	0.5512 (2)	0.0390 (5)
H14	0.2168	0.4439	0.4901	0.047*
C15	0.4909 (2)	0.5181 (2)	0.74641 (19)	0.0319 (4)
C16	0.5289 (2)	0.6148 (2)	0.86151 (19)	0.0317 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03296 (16)	0.03095 (16)	0.03298 (16)	0.00803 (11)	0.00661 (11)	0.00203 (10)
Cl1	0.0439 (4)	0.0748 (5)	0.0858 (5)	0.0241 (3)	0.0227 (3)	0.0012 (4)
Cl2	0.0413 (3)	0.0447 (3)	0.0484 (3)	−0.0015 (2)	0.0122 (3)	−0.0006 (3)
O1	0.0360 (8)	0.0378 (8)	0.0516 (9)	0.0094 (7)	0.0135 (7)	−0.0010 (7)
O2	0.0409 (10)	0.0442 (10)	0.0972 (16)	0.0042 (8)	0.0163 (10)	−0.0071 (10)
O3	0.0474 (9)	0.0287 (8)	0.0373 (8)	0.0040 (7)	−0.0002 (7)	0.0058 (6)
O4	0.0747 (13)	0.0462 (10)	0.0453 (10)	0.0019 (9)	−0.0113 (9)	0.0129 (8)
O5	0.0435 (9)	0.0342 (8)	0.0493 (9)	0.0040 (7)	0.0130 (7)	0.0051 (7)
N1	0.0344 (9)	0.0302 (9)	0.0328 (9)	0.0031 (7)	0.0105 (7)	0.0032 (7)
N2	0.0359 (9)	0.0312 (9)	0.0328 (9)	0.0052 (7)	0.0109 (8)	0.0037 (7)
C1	0.0357 (12)	0.0380 (12)	0.0352 (11)	0.0099 (10)	0.0078 (9)	0.0069 (9)
C2	0.0376 (12)	0.0416 (12)	0.0415 (12)	0.0122 (10)	0.0117 (10)	0.0041 (10)
C3	0.0399 (12)	0.0330 (11)	0.0340 (11)	0.0085 (9)	0.0069 (9)	0.0025 (9)
C4	0.0540 (15)	0.0334 (12)	0.0501 (14)	0.0061 (11)	0.0024 (12)	0.0077 (10)
C5	0.0457 (13)	0.0362 (12)	0.0372 (12)	0.0049 (10)	0.0129 (10)	−0.0011 (9)
C6	0.0548 (15)	0.0482 (14)	0.0327 (12)	−0.0027 (12)	0.0063 (11)	−0.0022 (10)
C7	0.0418 (13)	0.0490 (14)	0.0390 (12)	−0.0038 (11)	−0.0005 (10)	0.0114 (11)
C8	0.0344 (11)	0.0398 (12)	0.0409 (12)	0.0010 (9)	0.0090 (9)	0.0142 (10)
C9	0.0337 (12)	0.0546 (15)	0.0570 (15)	0.0110 (11)	0.0099 (11)	0.0230 (12)
C10	0.0400 (13)	0.0467 (14)	0.0657 (16)	0.0188 (11)	0.0217 (12)	0.0192 (12)
C11	0.0396 (12)	0.0326 (11)	0.0516 (13)	0.0075 (9)	0.0231 (10)	0.0129 (10)
C12	0.0530 (15)	0.0319 (12)	0.0609 (15)	0.0109 (10)	0.0316 (13)	0.0060 (10)
C13	0.0582 (15)	0.0329 (12)	0.0474 (14)	0.0002 (11)	0.0247 (12)	−0.0048 (10)
C14	0.0436 (12)	0.0339 (11)	0.0363 (11)	0.0008 (9)	0.0121 (10)	0.0005 (9)
C15	0.0326 (11)	0.0288 (10)	0.0370 (11)	0.0040 (8)	0.0145 (9)	0.0080 (8)
C16	0.0302 (10)	0.0313 (10)	0.0341 (11)	0.0024 (8)	0.0107 (9)	0.0091 (8)

Geometric parameters (Å, º) top

Cu1—O1	1.9427 (15)	C4—H4A	0.9700
Cu1—O3	1.9657 (15)	C4—H4B	0.9700
Cu1—N2	2.0052 (18)	C5—C6	1.399 (3)
Cu1—N1	2.0294 (18)	C5—H5A	0.9300
Cu1—O5	2.2531 (16)	C6—C7	1.361 (4)
Cl1—C2	1.778 (2)	C6—H6	0.9300
Cl1—Cl2ⁱ	3.3340 (10)	C7—C8	1.406 (3)
Cl2—C4	1.779 (3)	C7—H7	0.9300
O1—C1	1.279 (3)	C8—C16	1.398 (3)
O2—C1	1.226 (3)	C8—C9	1.435 (3)
O3—C3	1.251 (3)	C9—C10	1.346 (4)
O4—C3	1.231 (3)	C9—H9	0.9300
O5—H15	0.8498	C10—C11	1.434 (3)
O5—H16	0.8498	C10—H10	0.9300
N1—C5	1.324 (3)	C11—C15	1.398 (3)
N1—C16	1.357 (3)	C11—C12	1.408 (3)
N2—C14	1.336 (3)	C12—C13	1.363 (4)
N2—C15	1.357 (3)	C12—H12	0.9300
C1—C2	1.514 (3)	C13—C14	1.392 (3)
C2—H2A	0.9700	C13—H13	0.9300
C2—H2B	0.9700	C14—H14	0.9300
C3—C4	1.524 (3)	C15—C16	1.434 (3)

Cl1···Cl2ⁱ	3.334 (1)	Cg1···Cg2ⁱⁱ	3.621 (11)

O1—Cu1—O3	94.93 (7)	H4A—C4—H4B	107.7
O1—Cu1—N2	173.08 (7)	N1—C5—C6	122.4 (2)
O3—Cu1—N2	91.04 (7)	N1—C5—H5A	118.8
O1—Cu1—N1	91.67 (7)	C6—C5—H5A	118.8
O3—Cu1—N1	160.92 (7)	C7—C6—C5	119.7 (2)
N2—Cu1—N1	81.58 (7)	C7—C6—H6	120.2
O1—Cu1—O5	93.30 (6)	C5—C6—H6	120.2
O3—Cu1—O5	98.18 (6)	C6—C7—C8	119.7 (2)
N2—Cu1—O5	89.32 (7)	C6—C7—H7	120.1
N1—Cu1—O5	99.28 (7)	C8—C7—H7	120.1
C1—O1—Cu1	125.47 (14)	C16—C8—C7	116.6 (2)
C3—O3—Cu1	130.63 (14)	C16—C8—C9	118.6 (2)
Cu1—O5—H15	127.2	C7—C8—C9	124.8 (2)
Cu1—O5—H16	95.7	C10—C9—C8	121.3 (2)
H15—O5—H16	108.2	C10—C9—H9	119.3
C5—N1—C16	117.97 (19)	C8—C9—H9	119.3
C5—N1—Cu1	129.49 (16)	C9—C10—C11	121.2 (2)
C16—N1—Cu1	112.52 (13)	C9—C10—H10	119.4
C14—N2—C15	118.05 (19)	C11—C10—H10	119.4
C14—N2—Cu1	128.50 (16)	C15—C11—C12	116.5 (2)
C15—N2—Cu1	113.32 (13)	C15—C11—C10	118.7 (2)
O2—C1—O1	127.3 (2)	C12—C11—C10	124.8 (2)
O2—C1—C2	121.8 (2)	C13—C12—C11	119.9 (2)
O1—C1—C2	110.88 (19)	C13—C12—H12	120.0
C1—C2—Cl1	113.88 (16)	C11—C12—H12	120.0
C1—C2—H2A	108.8	C12—C13—C14	119.9 (2)
Cl1—C2—H2A	108.8	C12—C13—H13	120.0
C1—C2—H2B	108.8	C14—C13—H13	120.0
Cl1—C2—H2B	108.8	N2—C14—C13	122.0 (2)
H2A—C2—H2B	107.7	N2—C14—H14	119.0
O4—C3—O3	123.8 (2)	C13—C14—H14	119.0
O4—C3—C4	115.3 (2)	N2—C15—C11	123.6 (2)
O3—C3—C4	120.9 (2)	N2—C15—C16	116.28 (18)
C3—C4—Cl2	113.92 (17)	C11—C15—C16	120.1 (2)
C3—C4—H4A	108.8	N1—C16—C8	123.6 (2)
Cl2—C4—H4A	108.8	N1—C16—C15	116.28 (18)
C3—C4—H4B	108.8	C8—C16—C15	120.1 (2)
Cl2—C4—H4B	108.8

O3—Cu1—O1—C1	65.71 (18)	C5—C6—C7—C8	0.8 (4)
N2—Cu1—O1—C1	−144.9 (5)	C6—C7—C8—C16	0.0 (3)
N1—Cu1—O1—C1	−132.21 (18)	C6—C7—C8—C9	−179.0 (2)
O5—Cu1—O1—C1	−32.81 (18)	C16—C8—C9—C10	0.2 (3)
O1—Cu1—O3—C3	52.0 (2)	C7—C8—C9—C10	179.2 (2)
N2—Cu1—O3—C3	−124.4 (2)	C8—C9—C10—C11	−0.7 (4)
N1—Cu1—O3—C3	−57.7 (3)	C9—C10—C11—C15	1.0 (3)
O5—Cu1—O3—C3	146.1 (2)	C9—C10—C11—C12	−177.6 (2)
O1—Cu1—N1—C5	2.6 (2)	C15—C11—C12—C13	−1.2 (3)
O3—Cu1—N1—C5	112.9 (2)	C10—C11—C12—C13	177.4 (2)
N2—Cu1—N1—C5	−178.9 (2)	C11—C12—C13—C14	0.7 (4)
O5—Cu1—N1—C5	−91.01 (19)	C15—N2—C14—C13	−1.5 (3)
O1—Cu1—N1—C16	−179.12 (14)	Cu1—N2—C14—C13	−177.15 (17)
O3—Cu1—N1—C16	−68.8 (3)	C12—C13—C14—N2	0.7 (4)
N2—Cu1—N1—C16	−0.65 (14)	C14—N2—C15—C11	0.9 (3)
O5—Cu1—N1—C16	87.26 (14)	Cu1—N2—C15—C11	177.24 (16)
O1—Cu1—N2—C14	−170.8 (5)	C14—N2—C15—C16	−176.64 (18)
O3—Cu1—N2—C14	−21.29 (19)	Cu1—N2—C15—C16	−0.3 (2)
N1—Cu1—N2—C14	176.37 (19)	C12—C11—C15—N2	0.4 (3)
O5—Cu1—N2—C14	76.88 (19)	C10—C11—C15—N2	−178.3 (2)
O1—Cu1—N2—C15	13.4 (6)	C12—C11—C15—C16	177.90 (19)
O3—Cu1—N2—C15	162.87 (14)	C10—C11—C15—C16	−0.8 (3)
N1—Cu1—N2—C15	0.53 (14)	C5—N1—C16—C8	1.0 (3)
O5—Cu1—N2—C15	−98.96 (14)	Cu1—N1—C16—C8	−177.50 (16)
Cu1—O1—C1—O2	5.6 (3)	C5—N1—C16—C15	179.16 (18)
Cu1—O1—C1—C2	−172.99 (14)	Cu1—N1—C16—C15	0.7 (2)
O2—C1—C2—Cl1	6.1 (3)	C7—C8—C16—N1	−1.0 (3)
O1—C1—C2—Cl1	−175.31 (16)	C9—C8—C16—N1	178.1 (2)
Cu1—O3—C3—O4	−170.39 (19)	C7—C8—C16—C15	−179.08 (19)
Cu1—O3—C3—C4	9.1 (3)	C9—C8—C16—C15	0.0 (3)
O4—C3—C4—Cl2	−147.4 (2)	N2—C15—C16—N1	−0.2 (3)
O3—C3—C4—Cl2	33.1 (3)	C11—C15—C16—N1	−177.89 (18)
C16—N1—C5—C6	−0.1 (3)	N2—C15—C16—C8	178.01 (18)
Cu1—N1—C5—C6	178.14 (17)	C11—C15—C16—C8	0.3 (3)
N1—C5—C6—C7	−0.8 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H15···O4ⁱⁱⁱ	0.85	1.96	2.796 (2)	169

Symmetry code: (iii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₂H₂ClO₂)₂(C₁₂H₈N₂)(H₂O)]
M_r	448.73
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	8.7730 (6), 9.2382 (7), 11.4492 (8)
α, β, γ (°)	96.218 (1), 106.676 (1), 97.919 (1)
V (Å³)	869.66 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.59
Crystal size (mm)	0.38 × 0.25 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.583, 0.752
No. of measured, independent and observed [I > 2σ(I)] reflections	4610, 3057, 2837
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.074, 1.00
No. of reflections	3057
No. of parameters	235
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.29

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 1997), SHELXTL(Sheldrick, 1997.

Selected interatomic distances (Å) top

Cl1···Cl2ⁱ

3.334 (1)

Cg1···Cg2ⁱⁱ

3.621 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H15···O4ⁱⁱⁱ	0.85	1.96	2.796 (2)	168.8

Symmetry code: (iii) −x, −y+1, −z+1.

Acknowledgements

The authors thank the Postgraduate Foundation of Taishan University for financial support.

References

Chen, X. M., Tong, M. L., Wu, Y. L. & Luo, Y. J. (1996). J. Chem. Soc. Dalton Trans. pp. 2181–2182. CSD CrossRef Web of Science Google Scholar
Czylkowska, A., Kruszynski, R., Czakis-Sulikowska, D. & Bartczak, T. J. (2004). J. Coord. Chem. 57, 239–249. CrossRef CAS Google Scholar
Overgaard, J., Larsen, F. K., Schiott, B. & Lversen, B. B. (2003). J. Am. Chem. Soc. 125, 11088–11098. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXTL. Version 5.1. 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
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems Inc., Madison, Wisconsin, USA. Google Scholar
Sieroń, L. (2007). Acta Cryst. E63, m1659–m1661. Web of Science CSD CrossRef IUCr Journals Google Scholar