Aqua­bis(chloro­acetato-κO)bis­(pyridine-κN)copper(II)

In the title compound, [Cu(C₂H₂ClO₂)₂(C₅H₅N)₂(H₂O)], the Cu^II atom has a slightly distorted square-pyramidal coordination made up of two N atoms of the pyridine ligands and two O atoms of monodentate chloro­acetate anions in the basal plane, as well as the water O atom in the apical position. Both the Cu and the O_water atoms occupy special positions on a twofold rotation axis. O_water—H...O_carboxy hydrogen bonds link mol­ecules in the crystal structure into infinite chains, which run along the b axis, resulting in a C²₁(6)[R²₁(10)] graph-set motif.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.028
• wR factor = 0.069
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu          (2)       2.12

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2003) and publCIF (Westrip, 2007).

Aquabis(chloroacetato-κO)bis(pyridine-κN)copper(II)

Crystal data

[Cu(C2H2ClO2)2(C5H5N)2(H2O)]	F(000) = 868
Mr = 426.74	Dx = 1.627 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7451 reflections
a = 16.3650 (6) Å	θ = 2.3–30.1°
b = 5.8030 (2) Å	µ = 1.59 mm^−1
c = 18.3458 (6) Å	T = 295 K
β = 90.511 (3)°	Prism, dark blue
V = 1742.16 (10) Å^3	0.5 × 0.3 × 0.1 mm
Z = 4

Data collection

Kuma KM-4 CCD area-detector diffractometer	1525 independent reflections
Radiation source: CX-Mo12x0.4-S Seifert Mo tube	1522 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 8.2356 pixels mm^-1	θmax = 25.0°, θmin = 3.3°
ω scans	h = −19→19
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −6→6
Tmin = 0.612, Tmax = 0.862	l = −21→21
7787 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.069	w = 1/[σ^2(Fo^2) + (0.0302P)^2 + 2.8011P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
1525 reflections	Δρmax = 0.39 e Å^−3
114 parameters	Δρmin = −0.38 e Å^−3
0 restraints

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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 (Ų)

	x	y	z	Uiso*/Ueq
Cu	0.50000	0.15762 (6)	0.75000	0.0296 (1)
Cl	0.36996 (5)	0.46966 (14)	0.48366 (3)	0.0592 (3)
O1	0.50000	−0.2244 (4)	0.75000	0.0476 (9)
O2	0.44747 (10)	0.1458 (3)	0.65395 (9)	0.0405 (5)
O3	0.45154 (12)	0.5223 (3)	0.62994 (10)	0.0499 (6)
N1	0.60950 (11)	0.1995 (3)	0.70046 (10)	0.0333 (6)
C2	0.63501 (15)	0.0422 (4)	0.65219 (13)	0.0420 (8)
C3	0.71066 (16)	0.0556 (5)	0.61918 (14)	0.0467 (8)
C4	0.76144 (15)	0.2377 (5)	0.63518 (14)	0.0453 (8)
C5	0.73508 (14)	0.4021 (4)	0.68382 (14)	0.0427 (8)
C6	0.65925 (14)	0.3777 (4)	0.71528 (13)	0.0373 (7)
C7	0.44102 (13)	0.3215 (4)	0.61287 (12)	0.0355 (7)
C8	0.42029 (19)	0.2536 (5)	0.53452 (14)	0.0537 (9)
H1	0.4883 (18)	−0.289 (5)	0.7141 (15)	0.055 (9)*
H2	0.60070	−0.08030	0.64050	0.0500*
H3	0.72690	−0.05750	0.58650	0.0560*
H4	0.81250	0.24960	0.61370	0.0540*
H5	0.76800	0.52790	0.69530	0.0510*
H6	0.64190	0.48930	0.74810	0.0450*
H81	0.38590	0.11740	0.53530	0.0640*
H82	0.47050	0.21290	0.50990	0.0640*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0294 (2)	0.0282 (2)	0.0311 (2)	0.0000	−0.0066 (1)	0.0000
Cl	0.0686 (5)	0.0747 (5)	0.0343 (3)	0.0191 (4)	−0.0062 (3)	0.0101 (3)
O1	0.0747 (19)	0.0267 (12)	0.0411 (15)	0.0000	−0.0195 (14)	0.0000
O2	0.0420 (9)	0.0418 (9)	0.0373 (9)	−0.0022 (7)	−0.0138 (7)	0.0028 (7)
O3	0.0704 (12)	0.0375 (10)	0.0416 (10)	0.0052 (9)	−0.0091 (9)	−0.0060 (7)
N1	0.0318 (9)	0.0341 (10)	0.0340 (10)	0.0020 (8)	−0.0058 (8)	−0.0013 (8)
C2	0.0460 (13)	0.0371 (13)	0.0428 (13)	−0.0004 (10)	−0.0012 (11)	−0.0083 (10)
C3	0.0489 (14)	0.0464 (15)	0.0450 (14)	0.0095 (12)	0.0076 (11)	−0.0067 (11)
C4	0.0344 (12)	0.0549 (15)	0.0467 (14)	0.0066 (11)	0.0020 (10)	0.0057 (12)
C5	0.0352 (12)	0.0433 (13)	0.0495 (14)	−0.0036 (11)	−0.0049 (10)	0.0013 (12)
C6	0.0361 (12)	0.0358 (12)	0.0400 (12)	0.0027 (10)	−0.0042 (10)	−0.0051 (10)
C7	0.0333 (11)	0.0401 (13)	0.0331 (12)	0.0069 (10)	−0.0036 (9)	−0.0019 (10)
C8	0.0782 (19)	0.0444 (15)	0.0381 (14)	0.0099 (14)	−0.0176 (13)	−0.0013 (12)

Geometric parameters (Å, º)

Cu—O1	2.217 (2)	C4—C5	1.378 (4)
Cu—O2	1.9549 (16)	C5—C6	1.381 (3)
Cu—N1	2.0311 (18)	C7—C8	1.526 (3)
Cl—C8	1.763 (3)	C2—H2	0.93
O2—C7	1.272 (3)	C3—H3	0.93
O3—C7	1.218 (3)	C4—H4	0.93
O1—H1	0.78 (3)	C5—H5	0.93
N1—C6	1.343 (3)	C6—H6	0.93
N1—C2	1.341 (3)	C8—H81	0.97
C2—C3	1.385 (4)	C8—H82	0.97
C3—C4	1.374 (4)
O1—Cu—O2	87.99 (5)	O2—C7—C8	111.6 (2)
O1—Cu—N1	96.87 (5)	O3—C7—C8	121.3 (2)
O2—Cu—N1	89.05 (7)	Cl—C8—C7	114.5 (2)
O2—Cu—O2^i	175.98 (8)	N1—C2—H2	119
O2—Cu—N1^i	91.43 (7)	C3—C2—H2	119
N1—Cu—N1^i	166.26 (7)	C2—C3—H3	120
Cu—O2—C7	122.65 (15)	C4—C3—H3	120
H1—O1—H1^i	123 (3)	C3—C4—H4	121
Cu—O1—H1	119 (2)	C5—C4—H4	121
Cu—N1—C6	122.51 (15)	C4—C5—H5	120
Cu—N1—C2	119.68 (15)	C6—C5—H5	120
C2—N1—C6	117.8 (2)	N1—C6—H6	119
N1—C2—C3	122.4 (2)	C5—C6—H6	119
C2—C3—C4	119.4 (2)	Cl—C8—H81	109
C3—C4—C5	118.6 (2)	Cl—C8—H82	109
C4—C5—C6	119.2 (2)	C7—C8—H81	109
N1—C6—C5	122.7 (2)	C7—C8—H82	109
O2—C7—O3	127.1 (2)	H81—C8—H82	108

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^ii	0.78 (3)	1.98 (3)	2.759 (2)	174 (3)

Symmetry code: (ii) x, y−1, z.