Aqua-bis(dichloro-acetato-κO)(1,10-phenanthroline-κN,N')copper(II).

In the title complex, [Cu(C(2)HCl(2)O(2))(2)(C(12)H(8)N(2))(H(2)O)], the Cu(II) ion has a distorted square-pyramidal coordination geometry. The equatorial positions are occupied by two N atoms from a 1,10-phenanthroline ligand [Cu-N = 1.994 (3) and 2.027 (3) Å] and two O atoms from dichloro-acetate ligands and a water mol-ecule [Cu-O = 1.971 (2) and 1.939 (2) Å]. One O atom from another dichloro-acetate ligand occupies the apical positon [Cu-O = 2.152 (3) Å]. Inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers. The crystal packing also exhibits weak inter-molecular C-H⋯O hydrogen bonds, π-π inter-actions [centroid-centroid distance = 3.734 (2) Å] and short inter-molecular Cl⋯Cl contacts [3.306 (2) and 3.278 (2) Å].

Related literature

For applications of dichloro­acetic acid derivatives, see: Múdra et al. (2003 ▶); Lin et al. (2001 ▶); Zhu & Xiao (2006 ▶).

Experimental

Crystal data

[Cu(C2HCl2O2)2(C12H8N2)(H2O)]

M = 517.62

Triclinic,

a = 8.2701 (8) Å

b = 10.8883 (11) Å

c = 12.0125 (12) Å

α = 67.4390 (10)°

β = 77.585 (2)°

γ = 73.776 (2)°

V = 952.02 (16) Å3

Z = 2

Mo Kα radiation

μ = 1.74 mm−1

T = 273 (2) K

0.32 × 0.25 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.606, T max = 0.711

5043 measured reflections

3346 independent reflections

2539 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.106

S = 1.01

3346 reflections

261 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.51 e Å−3

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, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042578/cv2493sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042578/cv2493Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C2HCl2O2)2(C12H8N2)(H2O)]	Z = 2
Mr = 517.62	F(000) = 518
Triclinic, P1	Dx = 1.806 Mg m−3
a = 8.2701 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8883 (11) Å	Cell parameters from 1923 reflections
c = 12.0125 (12) Å	θ = 2.3–27.1°
α = 67.439 (1)°	µ = 1.74 mm−1
β = 77.585 (2)°	T = 273 K
γ = 73.776 (2)°	Block, colorless
V = 952.02 (16) Å3	0.32 × 0.25 × 0.21 mm

Bruker SMART CCD area-detector diffractometer	3346 independent reflections
Radiation source: fine-focus sealed tube	2539 reflections with I > 2σ(I)
graphite	Rint = 0.064
φ and ω scans	θmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.606, Tmax = 0.711	k = −12→12
5043 measured reflections	l = −14→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.046P)2] where P = (Fo2 + 2Fc2)/3
3346 reflections	(Δ/σ)max < 0.001
261 parameters	Δρmax = 0.63 e Å−3
3 restraints	Δρmin = −0.51 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cu1	0.23680 (6)	0.74569 (4)	0.41387 (4)	0.03375 (16)
Cl4	0.12884 (15)	0.83880 (10)	0.01776 (9)	0.0498 (3)
Cl3	0.18005 (19)	0.55281 (11)	0.05837 (10)	0.0653 (4)
Cl1	0.66991 (17)	0.90846 (12)	0.08639 (11)	0.0717 (4)
Cl2	0.5908 (2)	0.69108 (14)	0.04161 (11)	0.0831 (5)
O3	0.1567 (3)	0.7463 (2)	0.2733 (2)	0.0399 (6)
C5	0.2814 (4)	0.9060 (3)	0.5379 (3)	0.0310 (8)
O5	0.1749 (4)	0.5698 (3)	0.5130 (2)	0.0471 (7)
N2	0.1747 (4)	0.9522 (3)	0.3541 (2)	0.0324 (7)
N1	0.3082 (4)	0.7741 (3)	0.5489 (3)	0.0343 (7)
C9	0.0716 (5)	1.1808 (4)	0.2276 (3)	0.0447 (10)
H9	0.0263	1.2392	0.1564	0.054*
O2	0.7530 (4)	0.6097 (3)	0.2708 (2)	0.0586 (8)
C13	0.6067 (5)	0.6806 (4)	0.2683 (3)	0.0344 (8)
C16	0.0957 (5)	0.6794 (3)	0.1249 (3)	0.0340 (8)
H16	−0.0272	0.6861	0.1432	0.041*
C11	0.2127 (6)	1.1856 (4)	0.4993 (4)	0.0471 (10)
H11	0.1873	1.2779	0.4887	0.056*
C15	0.1639 (5)	0.6447 (3)	0.2447 (3)	0.0341 (8)
O4	0.2088 (4)	0.5243 (3)	0.3049 (2)	0.0609 (9)
C14	0.5542 (5)	0.7783 (4)	0.1437 (3)	0.0357 (9)
H14	0.4330	0.8198	0.1536	0.043*
C1	0.3872 (5)	0.6806 (4)	0.6436 (3)	0.0447 (10)
H1	0.4132	0.5893	0.6509	0.054*
C12	0.2859 (6)	1.0935 (4)	0.5985 (4)	0.0510 (11)
H12	0.3130	1.1242	0.6531	0.061*
C8	0.1025 (5)	1.2327 (4)	0.3051 (3)	0.0421 (10)
H8	0.0766	1.3264	0.2879	0.051*
C10	0.1075 (5)	1.0398 (4)	0.2542 (3)	0.0398 (9)
H10	0.0836	1.0063	0.2004	0.048*
C6	0.2062 (5)	1.0040 (3)	0.4314 (3)	0.0306 (8)
C7	0.1742 (5)	1.1436 (4)	0.4118 (3)	0.0368 (9)
C4	0.3223 (5)	0.9501 (4)	0.6208 (3)	0.0390 (9)
C2	0.4306 (6)	0.7160 (4)	0.7297 (4)	0.0506 (11)
H2	0.4810	0.6482	0.7955	0.061*
O1	0.5012 (4)	0.6801 (3)	0.3559 (2)	0.0634 (9)
C3	0.4009 (6)	0.8478 (4)	0.7199 (3)	0.0477 (10)
H3	0.4321	0.8710	0.7779	0.057*
H5A	0.192 (6)	0.535 (3)	0.458 (2)	0.065 (16)*
H5B	0.194 (6)	0.509 (3)	0.5816 (15)	0.068 (15)*

	U11	U22	U33	U12	U13	U23
Cu1	0.0471 (3)	0.0207 (2)	0.0318 (3)	−0.00140 (19)	−0.0107 (2)	−0.00826 (19)
Cl4	0.0728 (8)	0.0307 (5)	0.0416 (6)	−0.0135 (5)	−0.0179 (5)	−0.0005 (4)
Cl3	0.1158 (11)	0.0350 (6)	0.0486 (6)	−0.0027 (6)	−0.0209 (6)	−0.0222 (5)
Cl1	0.0801 (9)	0.0472 (7)	0.0746 (8)	−0.0293 (6)	−0.0338 (7)	0.0168 (6)
Cl2	0.1151 (12)	0.0745 (9)	0.0677 (8)	0.0119 (8)	−0.0340 (8)	−0.0440 (7)
O3	0.0622 (18)	0.0227 (13)	0.0366 (14)	−0.0029 (12)	−0.0151 (13)	−0.0119 (11)
C5	0.034 (2)	0.0258 (19)	0.0303 (18)	−0.0034 (15)	−0.0046 (16)	−0.0087 (15)
O5	0.073 (2)	0.0312 (15)	0.0346 (16)	−0.0132 (15)	−0.0142 (15)	−0.0038 (14)
N2	0.0419 (19)	0.0222 (16)	0.0315 (16)	−0.0044 (13)	−0.0051 (14)	−0.0090 (13)
N1	0.0420 (18)	0.0271 (17)	0.0326 (16)	−0.0042 (14)	−0.0059 (14)	−0.0104 (13)
C9	0.058 (3)	0.026 (2)	0.039 (2)	−0.0008 (18)	−0.014 (2)	−0.0011 (17)
O2	0.0396 (17)	0.0558 (19)	0.0453 (16)	0.0073 (15)	−0.0018 (14)	0.0063 (14)
C13	0.037 (2)	0.029 (2)	0.037 (2)	−0.0090 (17)	−0.0027 (18)	−0.0108 (17)
C16	0.041 (2)	0.0239 (19)	0.0350 (19)	−0.0038 (16)	−0.0062 (17)	−0.0094 (16)
C11	0.066 (3)	0.029 (2)	0.052 (2)	−0.010 (2)	−0.010 (2)	−0.018 (2)
C15	0.041 (2)	0.024 (2)	0.034 (2)	−0.0025 (16)	−0.0069 (17)	−0.0084 (16)
O4	0.113 (3)	0.0235 (15)	0.0449 (16)	0.0005 (16)	−0.0331 (17)	−0.0086 (13)
C14	0.032 (2)	0.030 (2)	0.039 (2)	−0.0029 (16)	−0.0048 (17)	−0.0088 (16)
C1	0.060 (3)	0.024 (2)	0.044 (2)	−0.0006 (19)	−0.018 (2)	−0.0048 (17)
C12	0.072 (3)	0.043 (3)	0.051 (3)	−0.018 (2)	−0.008 (2)	−0.026 (2)
C8	0.051 (3)	0.0200 (19)	0.047 (2)	−0.0035 (17)	−0.007 (2)	−0.0049 (17)
C10	0.051 (2)	0.030 (2)	0.035 (2)	−0.0034 (18)	−0.0145 (18)	−0.0065 (17)
C6	0.034 (2)	0.0242 (19)	0.0298 (18)	−0.0039 (15)	0.0009 (15)	−0.0097 (15)
C7	0.040 (2)	0.0229 (19)	0.042 (2)	−0.0055 (16)	−0.0010 (18)	−0.0088 (17)
C4	0.044 (2)	0.039 (2)	0.036 (2)	−0.0094 (18)	−0.0024 (18)	−0.0149 (18)
C2	0.063 (3)	0.043 (3)	0.040 (2)	−0.005 (2)	−0.020 (2)	−0.006 (2)
O1	0.0491 (19)	0.083 (2)	0.0386 (16)	0.0057 (16)	−0.0020 (15)	−0.0158 (16)
C3	0.057 (3)	0.052 (3)	0.038 (2)	−0.010 (2)	−0.014 (2)	−0.016 (2)

Cu1—O3	1.939 (2)	C13—O1	1.213 (4)
Cu1—O5	1.971 (2)	C13—C14	1.536 (5)
Cu1—N1	1.994 (3)	C16—C15	1.531 (5)
Cu1—N2	2.027 (3)	C16—H16	0.9800
Cu1—O1	2.152 (3)	C11—C12	1.359 (6)
Cl4—C16	1.774 (3)	C11—C7	1.417 (5)
Cl3—C16	1.759 (4)	C11—H11	0.9300
Cl1—C14	1.767 (4)	C15—O4	1.223 (4)
Cl2—C14	1.753 (4)	C14—H14	0.9800
O3—C15	1.261 (4)	C1—C2	1.374 (5)
C5—N1	1.348 (4)	C1—H1	0.9300
C5—C4	1.394 (5)	C12—C4	1.432 (5)
C5—C6	1.444 (5)	C12—H12	0.9300
O5—H5A	0.85 (3)	C8—C7	1.410 (5)
O5—H5B	0.85 (3)	C8—H8	0.9300
N2—C10	1.331 (4)	C10—H10	0.9300
N2—C6	1.355 (4)	C6—C7	1.401 (5)
N1—C1	1.348 (4)	C4—C3	1.411 (5)
C9—C8	1.355 (5)	C2—C3	1.349 (5)
C9—C10	1.399 (5)	C2—H2	0.9300
C9—H9	0.9300	C3—H3	0.9300
O2—C13	1.240 (5)
Cl1···Cl4i	3.306 (2)	Cg1···Cg2iii	3.734 (2)
Cl2···Cl3ii	3.278 (2)
O3—Cu1—O5	91.06 (10)	O4—C15—O3	127.3 (3)
O3—Cu1—N1	171.76 (11)	O4—C15—C16	117.8 (3)
O5—Cu1—N1	95.86 (11)	O3—C15—C16	114.7 (3)
O3—Cu1—N2	90.28 (11)	C13—C14—Cl2	110.9 (3)
O5—Cu1—N2	149.53 (12)	C13—C14—Cl1	109.3 (2)
N1—Cu1—N2	81.49 (11)	Cl2—C14—Cl1	110.0 (2)
O3—Cu1—O1	95.15 (11)	C13—C14—H14	108.9
O5—Cu1—O1	101.24 (12)	Cl2—C14—H14	108.9
N1—Cu1—O1	87.88 (12)	Cl1—C14—H14	108.9
N2—Cu1—O1	108.94 (12)	N1—C1—C2	122.1 (4)
C15—O3—Cu1	127.3 (2)	N1—C1—H1	118.9
N1—C5—C4	124.2 (3)	C2—C1—H1	119.0
N1—C5—C6	115.7 (3)	C11—C12—C4	121.4 (4)
C4—C5—C6	120.1 (3)	C11—C12—H12	119.3
Cu1—O5—H5A	99 (2)	C4—C12—H12	119.3
Cu1—O5—H5B	137 (3)	C9—C8—C7	119.6 (3)
H5A—O5—H5B	111 (3)	C9—C8—H8	120.2
C10—N2—C6	117.7 (3)	C7—C8—H8	120.2
C10—N2—Cu1	129.8 (3)	N2—C10—C9	121.9 (4)
C6—N2—Cu1	112.5 (2)	N2—C10—H10	119.0
C1—N1—C5	117.1 (3)	C9—C10—H10	119.1
C1—N1—Cu1	128.6 (3)	N2—C6—C7	124.1 (3)
C5—N1—Cu1	114.1 (2)	N2—C6—C5	116.1 (3)
C8—C9—C10	120.4 (4)	C7—C6—C5	119.8 (3)
C8—C9—H9	119.8	C6—C7—C8	116.3 (3)
C10—C9—H9	119.8	C6—C7—C11	118.9 (3)
O1—C13—O2	125.7 (4)	C8—C7—C11	124.7 (3)
O1—C13—C14	117.0 (3)	C5—C4—C3	116.3 (3)
O2—C13—C14	117.3 (3)	C5—C4—C12	118.5 (3)
C15—C16—Cl3	113.0 (3)	C3—C4—C12	125.2 (3)
C15—C16—Cl4	112.4 (2)	C3—C2—C1	120.8 (3)
Cl3—C16—Cl4	109.30 (19)	C3—C2—H2	119.6
C15—C16—H16	107.3	C1—C2—H2	119.6
Cl3—C16—H16	107.3	C13—O1—Cu1	144.6 (3)
Cl4—C16—H16	107.3	C2—C3—C4	119.4 (3)
C12—C11—C7	121.2 (4)	C2—C3—H3	120.3
C12—C11—H11	119.4	C4—C3—H3	120.3
C7—C11—H11	119.4

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2iv	0.98	2.24	3.118 (5)	149
O5—H5B···O2v	0.85 (2)	1.81 (2)	2.654 (3)	174 (3)
O5—H5A···O4	0.85 (2)	1.86 (2)	2.673 (4)	159 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O2i	0.98	2.24	3.118 (5)	149
O5—H5B⋯O2ii	0.85 (2)	1.81 (2)	2.654 (3)	174 (3)
O5—H5A⋯O4	0.85 (2)	1.86 (2)	2.673 (4)	159 (3)

Symmetry codes: (i) ; (ii) .