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The crystal structure of the title compound, [Cu2(C2H3O2)4(C5H6N2)2], previously reported by Antsyshkina, Porai-Koshits, Ostrikova, Garnovskii, Sadimenko & Osipov [Koord. Khim. (1987), 13, 836–842] has been redetermined from new intensity data, with appreciably improved precision and successful location of all H atoms. The dinuclear copper unit has crystallographic inversion symmetry with a Cu...Cu distance of 2.6771 (4) Å. The crystal packing is characterized by C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804008347/bt6443sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804008347/bt6443Isup2.hkl
Contains datablock I

CCDC reference: 239056

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.025
  • wR factor = 0.067
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2 ... ? PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.17 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXTL (Sheldrick, 2003); molecular graphics: SHELXTL; software used to prepare material for publication: PLATON (Spek, 1990).

tetrakis(µ-acetato-κ2O:O')bis[(2-aminopyridine-κN)copper(II)] top
Crystal data top
[Cu2(C2H3O2)4(C5H6N2)2]F(000) = 564
Mr = 551.51Dx = 1.690 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8156 reflections
a = 7.4498 (3) Åθ = 2.8–27.5°
b = 19.6500 (7) ŵ = 2.02 mm1
c = 8.1251 (4) ÅT = 293 K
β = 114.316 (4)°Prism, green
V = 1083.91 (9) Å30.36 × 0.30 × 0.12 mm
Z = 2
Data collection top
Kuma KM4CCD
diffractometer
2483 independent reflections
Radiation source: CX-Mo12x0.4-S Seifert Mo tube2143 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: numerical
(XRED; Stoe & Cie, 1999)
h = 98
Tmin = 0.500, Tmax = 0.782k = 2525
12569 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: difference Fourier map
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0394P)2]
where P = (Fo2 + 2Fc2)/3
2483 reflections(Δ/σ)max < 0.001
165 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.38 e Å3
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 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 (Å2) top
xyzUiso*/Ueq
Cu0.09277 (3)0.055741 (10)0.01936 (3)0.02434 (8)
O10.17565 (19)0.08086 (7)0.19745 (18)0.0350 (3)
O20.32930 (19)0.01245 (7)0.16681 (18)0.0376 (3)
O30.0287 (2)0.09418 (7)0.17539 (18)0.0368 (3)
O40.1263 (2)0.00086 (7)0.20597 (18)0.0344 (3)
C10.3274 (3)0.04499 (9)0.2351 (2)0.0283 (4)
C20.5191 (3)0.07209 (11)0.3742 (3)0.0405 (5)
H210.52700.06270.49290.076 (9)*
H220.52530.12030.35890.079 (9)*
H230.62700.05050.35940.073 (9)*
C30.0617 (3)0.06014 (9)0.2492 (2)0.0282 (4)
C40.0937 (3)0.09335 (12)0.4027 (3)0.0433 (5)
H410.22760.08650.38630.097 (11)*
H420.06760.14120.40420.086 (10)*
H430.00640.07340.51510.086 (10)*
C50.4497 (3)0.13722 (10)0.0010 (3)0.0336 (4)
H50.50320.09560.05260.033 (5)*
C60.5743 (3)0.18548 (11)0.0123 (3)0.0400 (5)
H60.70870.17720.02930.054 (7)*
C70.4939 (3)0.24751 (11)0.0901 (3)0.0451 (5)
H70.57470.28150.10200.066 (8)*
C80.2965 (4)0.25852 (11)0.1491 (3)0.0466 (5)
H80.24170.30000.20030.077 (9)*
C90.1773 (3)0.20625 (10)0.1311 (3)0.0352 (4)
N10.2529 (2)0.14591 (7)0.0562 (2)0.0276 (3)
N20.0201 (3)0.21568 (12)0.1860 (4)0.0632 (7)
H10.106 (4)0.1785 (17)0.207 (4)0.079 (9)*
H20.066 (4)0.2479 (16)0.248 (4)0.071 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.02393 (13)0.02409 (13)0.02417 (12)0.00019 (8)0.00907 (9)0.00071 (8)
O10.0264 (7)0.0332 (7)0.0392 (7)0.0019 (6)0.0072 (6)0.0059 (6)
O20.0288 (7)0.0385 (8)0.0364 (7)0.0007 (6)0.0042 (6)0.0093 (6)
O30.0482 (8)0.0323 (7)0.0373 (7)0.0068 (6)0.0250 (6)0.0075 (6)
O40.0433 (8)0.0318 (7)0.0351 (7)0.0014 (6)0.0232 (6)0.0029 (6)
C10.0271 (9)0.0325 (10)0.0236 (8)0.0054 (7)0.0086 (7)0.0020 (7)
C20.0308 (11)0.0433 (12)0.0361 (11)0.0082 (9)0.0024 (9)0.0045 (9)
C30.0294 (9)0.0312 (10)0.0224 (8)0.0090 (7)0.0091 (7)0.0021 (7)
C40.0588 (14)0.0442 (13)0.0328 (10)0.0101 (11)0.0249 (10)0.0019 (9)
C50.0332 (10)0.0288 (10)0.0397 (10)0.0001 (8)0.0158 (9)0.0013 (8)
C60.0354 (11)0.0374 (11)0.0506 (12)0.0052 (8)0.0212 (10)0.0037 (9)
C70.0555 (14)0.0332 (11)0.0547 (13)0.0123 (10)0.0308 (12)0.0016 (10)
C80.0592 (14)0.0268 (10)0.0517 (13)0.0004 (10)0.0208 (11)0.0104 (9)
C90.0376 (10)0.0270 (10)0.0370 (10)0.0024 (8)0.0115 (8)0.0035 (8)
N10.0287 (8)0.0246 (7)0.0293 (7)0.0008 (6)0.0118 (6)0.0015 (6)
N20.0401 (11)0.0349 (11)0.0975 (18)0.0092 (9)0.0110 (11)0.0185 (12)
Geometric parameters (Å, º) top
Cu—O11.9883 (13)C4—H410.96
Cu—O21.9803 (13)C4—H420.96
Cu—O31.9811 (13)C4—H430.96
Cu—O41.9773 (13)C5—N11.355 (2)
Cu—N12.2239 (15)C5—C61.362 (3)
Cu—Cui2.6771 (4)C5—H50.93
O1—C11.259 (2)C6—C71.390 (3)
O2—C1i1.260 (2)C6—H60.93
O3—C31.262 (2)C7—C81.363 (3)
O4—C3i1.254 (2)C7—H70.93
C1—O2i1.260 (2)C8—C91.404 (3)
C1—C21.507 (3)C8—H80.93
C2—H210.96C9—N11.346 (2)
C2—H220.96C9—N21.362 (3)
C2—H230.96N2—H10.94 (3)
C3—O4i1.254 (2)N2—H20.79 (3)
C3—C41.511 (2)
O1—Cu—O2167.03 (6)O4i—C3—C4117.37 (17)
O1—Cu—O389.18 (6)O3—C3—C4117.38 (17)
O1—Cu—O489.32 (6)C3—C4—H41109.5
O2—Cu—O389.14 (6)C3—C4—H42109.5
O2—Cu—O489.46 (6)H41—C4—H42109.5
O3—Cu—O4167.15 (5)C3—C4—H43109.5
N1—Cu—O197.97 (6)H41—C4—H43109.5
N1—Cu—O295.00 (5)H42—C4—H43109.5
N1—Cu—O397.05 (5)N1—C5—C6124.18 (19)
N1—Cu—O495.80 (5)N1—C5—H5117.9
O1—Cu—Cui82.84 (4)C6—C5—H5117.9
O2—Cu—Cui84.19 (4)C5—C6—C7117.82 (19)
O3—Cu—Cui84.96 (4)C5—C6—H6121.1
O4—Cu—Cui82.19 (4)C7—C6—H6121.1
N1—Cu—Cui177.83 (4)C8—C7—C6119.95 (19)
C1—O1—Cu124.85 (12)C8—C7—H7120.0
C1i—O2—Cu123.59 (12)C6—C7—H7120.0
C3—O3—Cu121.92 (12)C7—C8—C9119.0 (2)
C3i—O4—Cu125.63 (12)C7—C8—H8120.5
O1—C1—O2i124.49 (17)C9—C8—H8120.5
O1—C1—C2117.60 (17)N1—C9—N2117.49 (19)
O2i—C1—C2117.90 (17)N1—C9—C8121.81 (18)
C1—C2—H21109.5N2—C9—C8120.7 (2)
C1—C2—H22109.5C9—N1—C5117.27 (16)
H21—C2—H22109.5C9—N1—Cu127.98 (12)
C1—C2—H23109.5C5—N1—Cu114.73 (12)
H21—C2—H23109.5C9—N2—H1121.2 (18)
H22—C2—H23109.5C9—N2—H2116 (2)
O4i—C3—O3125.25 (16)H1—N2—H2115 (3)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O10.94 (3)2.00 (3)2.878 (3)155 (3)
C5—H5···O20.932.493.103 (3)124
C8—H8···O3ii0.932.563.471 (3)167
C4—H43···O4iii0.962.533.454 (3)162
Symmetry codes: (ii) x, y+1/2, z1/2; (iii) x, y, z+1.
 

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