Di-μ-iodo­acetato-bis­[(2,2′-bipyrid­yl)(iodo­acetato)copper(II)] hemihydrate

The title compound, [Cu₂(C₂H₂IO₂)₄(C₁₀H₈N₂)₂]·0.5H₂O, is a copper(II) dimer, in which two Cu atoms are joined by two oxo bridges of iodo­acetate groups. The distorted square-pyramidal environment of each Cu atom is completed by two N atoms of the 2,2′-bipyridine ligands (bpy), one iodo­acetate O atom and two bridging iodo­acetate O atoms. The dimer lies on an inversion center midway between the two Cu atoms.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.011 Å
• Disorder in solvent or counterion
• R factor = 0.047
• wR factor = 0.131
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         11
PLAT480_ALERT_4_C Long H...A H-Bond Reported H52    ..  O3      ..       2.69 Ang.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C28 H26 Cu2 I4 N4 O9
            Atom count from _chemical_formula_moiety:C28 H25 Cu2 I4 N4 O8.5

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

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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Di-µ-iodoacetato-bis[(2,2'-bipyridyl)(iodoacetato)copper(II)] hemihydrate

Crystal data

[Cu2(C2H2IO2)4(C10H8N2)2]·0.5H2O	Z = 1
Mr = 1197.21	F(000) = 564
Triclinic, P1	Dx = 2.223 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.447 (3) Å	Cell parameters from 2929 reflections
b = 9.631 (4) Å	θ = 2.3–27.0°
c = 10.410 (4) Å	µ = 4.69 mm^−1
α = 93.485 (4)°	T = 298 K
β = 107.740 (5)°	Block, blue
γ = 95.205 (4)°	0.50 × 0.40 × 0.10 mm
V = 894.5 (6) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3076 independent reflections
Radiation source: fine-focus sealed tube	2745 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −10→11
Tmin = 0.119, Tmax = 0.625	k = −11→11
3664 measured reflections	l = −12→6

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0585P)^2 + 4.6211P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3076 reflections	Δρmax = 1.46 e Å^−3
218 parameters	Δρmin = −0.99 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2604 (8)	−0.1936 (7)	0.0301 (7)	0.0422 (16)
H1	0.2075	−0.2008	0.0920	0.051*
C2	0.3350 (8)	−0.3041 (7)	0.0058 (8)	0.0429 (16)
H2	0.3325	−0.3844	0.0508	0.051*
C3	0.4131 (8)	−0.2936 (7)	−0.0858 (8)	0.0452 (17)
H3	0.4635	−0.3672	−0.1040	0.054*
C4	0.4160 (8)	−0.1729 (8)	−0.1508 (8)	0.0435 (16)
H4	0.4693	−0.1639	−0.2123	0.052*
C5	0.3383 (6)	−0.0651 (6)	−0.1229 (6)	0.0318 (13)
C6	0.3319 (7)	0.0683 (7)	−0.1856 (6)	0.0343 (14)
C7	0.4028 (8)	0.1029 (8)	−0.2802 (7)	0.0431 (16)
H7	0.4592	0.0403	−0.3083	0.052*
C8	0.3885 (10)	0.2317 (9)	−0.3324 (8)	0.056 (2)
H8	0.4363	0.2568	−0.3950	0.067*
C9	0.3031 (9)	0.3221 (8)	−0.2909 (8)	0.0495 (18)
H9	0.2910	0.4084	−0.3258	0.059*
C10	0.2354 (8)	0.2820 (7)	−0.1962 (7)	0.0442 (16)
H10	0.1781	0.3431	−0.1673	0.053*
C11	0.1762 (7)	0.0379 (7)	0.2564 (7)	0.0366 (14)
C12	0.1623 (9)	0.3627 (7)	0.1112 (7)	0.0450 (17)
C13	0.0788 (12)	0.4608 (9)	0.1710 (9)	0.063 (2)
H13B	−0.0102	0.4794	0.1009	0.076*
H13A	0.1415	0.5491	0.2045	0.076*
C14	0.1150 (8)	−0.0026 (8)	0.3695 (7)	0.0443 (16)
H14A	0.0066	−0.0175	0.3361	0.053*
H14B	0.1449	0.0718	0.4428	0.053*
Cu1	0.16059 (8)	0.09108 (8)	−0.00409 (8)	0.0331 (2)
I1	0.01618 (7)	0.37525 (6)	0.33228 (5)	0.0583 (2)
I2	0.20248 (9)	−0.19151 (6)	0.44062 (6)	0.0730 (3)
N1	0.2495 (6)	0.1577 (6)	−0.1446 (5)	0.0350 (12)
N2	0.2617 (6)	−0.0763 (5)	−0.0326 (5)	0.0346 (12)
O1	0.0843 (5)	0.0122 (5)	0.1361 (4)	0.0381 (10)
O2	0.0810 (6)	0.2637 (5)	0.0287 (5)	0.0447 (11)
O3	0.3042 (6)	0.0930 (6)	0.2836 (6)	0.0570 (14)
O4	0.2989 (7)	0.3843 (7)	0.1421 (7)	0.0676 (16)
O5W	0.5107 (14)	0.3883 (11)	0.4079 (10)	0.056 (3)	0.50
H51	0.4937	0.4324	0.3415	0.067*	0.50
H52	0.5156	0.3105	0.3958	0.067*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.041 (4)	0.043 (4)	0.042 (4)	0.001 (3)	0.013 (3)	0.008 (3)
C2	0.038 (4)	0.034 (3)	0.054 (4)	0.008 (3)	0.010 (3)	0.006 (3)
C3	0.037 (4)	0.040 (4)	0.057 (5)	0.012 (3)	0.011 (3)	0.001 (3)
C4	0.035 (4)	0.050 (4)	0.047 (4)	0.007 (3)	0.016 (3)	−0.003 (3)
C5	0.025 (3)	0.036 (3)	0.033 (3)	0.003 (2)	0.009 (3)	0.001 (3)
C6	0.032 (3)	0.040 (3)	0.027 (3)	−0.001 (3)	0.006 (3)	−0.003 (3)
C7	0.046 (4)	0.046 (4)	0.040 (4)	0.005 (3)	0.019 (3)	0.002 (3)
C8	0.064 (5)	0.068 (5)	0.040 (4)	−0.001 (4)	0.022 (4)	0.012 (4)
C9	0.061 (5)	0.047 (4)	0.046 (4)	0.008 (3)	0.021 (4)	0.014 (3)
C10	0.051 (4)	0.041 (4)	0.045 (4)	0.011 (3)	0.018 (3)	0.012 (3)
C11	0.038 (4)	0.036 (3)	0.037 (4)	0.011 (3)	0.012 (3)	0.005 (3)
C12	0.065 (5)	0.035 (3)	0.044 (4)	0.012 (3)	0.028 (4)	0.011 (3)
C13	0.104 (7)	0.046 (4)	0.063 (5)	0.021 (4)	0.056 (5)	0.009 (4)
C14	0.048 (4)	0.054 (4)	0.036 (4)	0.010 (3)	0.019 (3)	0.009 (3)
Cu1	0.0372 (4)	0.0349 (4)	0.0317 (4)	0.0091 (3)	0.0156 (3)	0.0051 (3)
I1	0.0787 (4)	0.0642 (4)	0.0453 (3)	0.0242 (3)	0.0331 (3)	0.0117 (2)
I2	0.1289 (6)	0.0463 (3)	0.0491 (4)	0.0124 (3)	0.0328 (4)	0.0159 (2)
N1	0.035 (3)	0.040 (3)	0.030 (3)	0.007 (2)	0.011 (2)	0.004 (2)
N2	0.034 (3)	0.036 (3)	0.033 (3)	0.005 (2)	0.010 (2)	0.004 (2)
O1	0.043 (3)	0.047 (3)	0.027 (2)	0.010 (2)	0.0128 (19)	0.0059 (19)
O2	0.052 (3)	0.040 (3)	0.046 (3)	0.014 (2)	0.018 (2)	−0.001 (2)
O3	0.043 (3)	0.074 (4)	0.051 (3)	−0.006 (3)	0.012 (2)	0.010 (3)
O4	0.057 (4)	0.069 (4)	0.074 (4)	−0.006 (3)	0.023 (3)	−0.007 (3)
O5W	0.104 (9)	0.050 (6)	0.036 (5)	0.051 (6)	0.038 (6)	0.018 (4)

Geometric parameters (Å, º)

C1—N2	1.339 (9)	C11—O3	1.217 (8)
C1—C2	1.380 (10)	C11—O1	1.282 (8)
C1—H1	0.9300	C11—C14	1.516 (9)
C2—C3	1.376 (11)	C12—O4	1.226 (10)
C2—H2	0.9300	C12—O2	1.266 (9)
C3—C4	1.383 (11)	C12—C13	1.505 (11)
C3—H3	0.9300	C13—I1	2.130 (8)
C4—C5	1.390 (9)	C13—H13B	0.9700
C4—H4	0.9300	C13—H13A	0.9700
C5—N2	1.354 (8)	C14—I2	2.146 (7)
C5—C6	1.474 (9)	C14—H14A	0.9700
C6—N1	1.345 (9)	C14—H14B	0.9700
C6—C7	1.389 (9)	Cu1—O2	1.939 (5)
C7—C8	1.385 (11)	Cu1—O1	1.976 (4)
C7—H7	0.9300	Cu1—N2	1.998 (5)
C8—C9	1.374 (12)	Cu1—N1	2.006 (5)
C8—H8	0.9300	Cu1—O1^i	2.390 (5)
C9—C10	1.385 (10)	O1—Cu1^i	2.390 (5)
C9—H9	0.9300	O5W—H51	0.8150
C10—N1	1.342 (9)	O5W—H52	0.7604
C10—H10	0.9300
N2—C1—C2	122.2 (7)	O2—C12—C13	115.1 (7)
N2—C1—H1	118.9	C12—C13—I1	111.5 (5)
C2—C1—H1	118.9	C12—C13—H13B	109.3
C3—C2—C1	119.0 (7)	I1—C13—H13B	109.3
C3—C2—H2	120.5	C12—C13—H13A	109.3
C1—C2—H2	120.5	I1—C13—H13A	109.3
C2—C3—C4	119.5 (7)	H13B—C13—H13A	108.0
C2—C3—H3	120.2	C11—C14—I2	108.2 (5)
C4—C3—H3	120.2	C11—C14—H14A	110.1
C3—C4—C5	119.0 (7)	I2—C14—H14A	110.1
C3—C4—H4	120.5	C11—C14—H14B	110.1
C5—C4—H4	120.5	I2—C14—H14B	110.1
N2—C5—C4	121.1 (6)	H14A—C14—H14B	108.4
N2—C5—C6	114.5 (5)	O2—Cu1—O1	88.3 (2)
C4—C5—C6	124.4 (6)	O2—Cu1—N2	174.6 (2)
N1—C6—C7	121.0 (6)	O1—Cu1—N2	94.3 (2)
N1—C6—C5	114.6 (5)	O2—Cu1—N1	96.4 (2)
C7—C6—C5	124.5 (6)	O1—Cu1—N1	175.0 (2)
C8—C7—C6	119.3 (7)	N2—Cu1—N1	80.8 (2)
C8—C7—H7	120.4	O2—Cu1—O1^i	90.21 (19)
C6—C7—H7	120.4	O1—Cu1—O1^i	78.46 (18)
C9—C8—C7	119.5 (7)	N2—Cu1—O1^i	94.95 (19)
C9—C8—H8	120.3	N1—Cu1—O1^i	102.97 (19)
C7—C8—H8	120.3	C10—N1—C6	119.4 (6)
C8—C9—C10	118.6 (7)	C10—N1—Cu1	125.5 (5)
C8—C9—H9	120.7	C6—N1—Cu1	115.1 (4)
C10—C9—H9	120.7	C1—N2—C5	119.2 (6)
N1—C10—C9	122.2 (7)	C1—N2—Cu1	125.8 (5)
N1—C10—H10	118.9	C5—N2—Cu1	115.0 (4)
C9—C10—H10	118.9	C11—O1—Cu1	113.6 (4)
O3—C11—O1	124.6 (6)	C11—O1—Cu1^i	144.8 (4)
O3—C11—C14	119.8 (6)	Cu1—O1—Cu1^i	101.54 (18)
O1—C11—C14	115.6 (6)	C12—O2—Cu1	120.9 (5)
O4—C12—O2	125.3 (7)	H51—O5W—H52	116.5
O4—C12—C13	119.6 (8)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3^ii	0.93	2.52	3.387 (9)	155
C3—H3···O4^ii	0.93	2.41	3.139 (10)	135
C2—H2···O4^iii	0.93	2.51	3.430 (10)	172
O5W—H52···O3	0.76	2.69	3.252 (13)	132
O5W—H51···O4	0.82	2.30	2.874 (12)	127

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