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The title compound, [Cu2Cl2(C8H14O2)2], exhibits a non-planar four-membered Cu2Cl2 ring, with one alkyne ligand coordinated to each Cu atom. Due to the presence of the Cl bridges as potential hydrogen-bond acceptor sites, one of the hydroxy substituents is engaged in an intra­molecular hydrogen bond, whereas the remaining three OH groups form inter­molecular inter­actions which sustain the supra­molecular structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009580/bg2029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009580/bg2029Isup2.hkl
Contains datablock I

CCDC reference: 642903

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.052
  • wR factor = 0.143
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

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Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.98 Deg. PLAT366_ALERT_2_B Short? C(sp?)-C(sp?) Bond C1 - C2 ... 1.23 Ang. PLAT366_ALERT_2_B Short? C(sp?)-C(sp?) Bond C9 - C10 ... 1.22 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H1 .. H4 .. 2.00 Ang.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.370 0.680 Tmin and Tmax expected: 0.315 0.691 RR = 1.194 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.20 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.02 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 200 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.52 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for Cl1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: SET4 (Boer et al., 1984); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXL97.

Di-µ-chloro-bis[(3,4-η)-(2,5-dimethylhex-3-yne-2,5-diol)copper(I)] top
Crystal data top
[Cu2Cl2(C8H14O2)2]Z = 2
Mr = 482.36F(000) = 496
Triclinic, P1Dx = 1.533 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.981 (2) ÅCell parameters from 25 reflections
b = 11.056 (2) Åθ = 16.9–23.4°
c = 11.676 (2) ŵ = 2.31 mm1
α = 92.11 (3)°T = 293 K
β = 112.13 (3)°Plate, colourless
γ = 101.39 (3)°0.52 × 0.47 × 0.16 mm
V = 1044.9 (3) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
3102 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.015
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
ω/2θ scansh = 109
Absorption correction: ψ scan
(North et al., 1968)
k = 1213
Tmin = 0.37, Tmax = 0.68l = 139
3859 measured reflections3 standard reflections every 600 min
3666 independent reflections intensity decay: 0.1%
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0904P)2 + 0.5653P]
where P = (Fo2 + 2Fc2)/3
3666 reflections(Δ/σ)max < 0.001
233 parametersΔρmax = 1.22 e Å3
4 restraintsΔρmin = 1.25 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 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
xyzUiso*/Ueq
Cu10.14223 (6)0.14132 (4)0.64959 (5)0.0478 (2)
Cu20.26375 (6)0.08200 (4)0.76057 (5)0.0496 (2)
Cl10.39491 (13)0.09160 (10)0.70668 (14)0.0664 (4)
Cl20.00668 (12)0.04989 (9)0.66288 (12)0.0557 (3)
C10.0253 (4)0.2793 (3)0.6364 (3)0.0351 (7)
C20.1577 (4)0.3213 (3)0.6281 (3)0.0343 (7)
C30.1380 (4)0.2718 (3)0.6450 (3)0.0365 (8)
C40.1321 (5)0.2346 (5)0.7696 (4)0.0558 (11)
H4A0.05030.29560.83500.084*
H4B0.10420.15510.77970.084*
H4C0.23820.22960.77330.084*
C50.2747 (5)0.1831 (4)0.5375 (4)0.0539 (10)
H5A0.28330.21440.46020.081*
H5B0.37750.17620.54700.081*
H5C0.24930.10270.53750.081*
O10.1704 (3)0.3947 (2)0.6389 (3)0.0488 (7)
H10.15870.42290.57810.083*
C60.2971 (5)0.4057 (3)0.6109 (3)0.0373 (8)
C70.4546 (5)0.4247 (4)0.7263 (4)0.0557 (11)
H7A0.43370.44780.79800.084*
H7B0.53750.48950.71840.084*
H7C0.49250.34900.73590.084*
C80.3169 (5)0.3544 (4)0.4963 (4)0.0489 (10)
H8A0.40160.41170.48190.073*
H8B0.21450.34330.42530.073*
H8C0.34710.27590.50920.073*
O20.2552 (4)0.5242 (3)0.5895 (3)0.0595 (8)
H20.20990.54080.63540.101*
C90.4294 (4)0.1741 (3)0.8578 (4)0.0416 (9)
C100.2934 (5)0.2356 (3)0.8441 (4)0.0396 (8)
C110.6122 (5)0.1322 (4)0.8937 (4)0.0538 (11)
C120.6951 (7)0.2134 (7)0.9904 (5)0.0857 (18)
H12A0.81220.17951.02680.129*
H12B0.67320.29630.95080.129*
H12C0.65210.21531.05430.129*
C130.6534 (6)0.1416 (5)0.7814 (5)0.0701 (14)
H13A0.76970.10980.80510.105*
H13B0.59320.09410.72080.105*
H13C0.62370.22710.74640.105*
O30.6677 (4)0.0089 (3)0.9558 (4)0.0895 (14)
H30.62460.03820.90770.152*
C140.1655 (5)0.3394 (3)0.8508 (4)0.0420 (8)
C150.0300 (5)0.2931 (4)0.8737 (4)0.0545 (11)
H15A0.07680.23880.95070.082*
H15B0.04990.36260.87820.082*
H15C0.02280.24860.80660.082*
C160.2469 (7)0.4151 (5)0.9527 (5)0.0749 (15)
H16B0.33040.44520.93550.112*
H16A0.16520.48420.95560.112*
H16C0.29640.36361.03160.112*
O40.0951 (4)0.4130 (3)0.7320 (3)0.0599 (8)
H40.01370.46520.72740.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0374 (3)0.0288 (3)0.0905 (4)0.0138 (2)0.0354 (3)0.0211 (2)
Cu20.0324 (3)0.0306 (3)0.0899 (4)0.0121 (2)0.0250 (3)0.0172 (2)
Cl10.0375 (5)0.0393 (5)0.1386 (11)0.0164 (4)0.0465 (6)0.0325 (6)
Cl20.0331 (5)0.0355 (5)0.1021 (8)0.0106 (4)0.0272 (5)0.0287 (5)
C10.0311 (18)0.0297 (17)0.0450 (19)0.0108 (14)0.0132 (15)0.0087 (14)
C20.0347 (19)0.0248 (16)0.0461 (19)0.0103 (14)0.0168 (15)0.0100 (14)
C30.0268 (17)0.0303 (17)0.053 (2)0.0100 (14)0.0144 (15)0.0081 (15)
C40.046 (2)0.069 (3)0.062 (3)0.017 (2)0.030 (2)0.020 (2)
C50.036 (2)0.046 (2)0.069 (3)0.0045 (18)0.0116 (19)0.001 (2)
O10.0392 (15)0.0370 (14)0.075 (2)0.0176 (12)0.0231 (14)0.0109 (13)
C60.0386 (19)0.0249 (17)0.054 (2)0.0071 (15)0.0231 (17)0.0119 (15)
C70.039 (2)0.050 (2)0.067 (3)0.0009 (19)0.015 (2)0.006 (2)
C80.050 (2)0.041 (2)0.064 (3)0.0069 (18)0.033 (2)0.0106 (18)
O20.072 (2)0.0299 (14)0.099 (2)0.0171 (14)0.0542 (19)0.0222 (14)
C90.0320 (19)0.0317 (18)0.060 (2)0.0108 (16)0.0153 (17)0.0005 (16)
C100.039 (2)0.0304 (18)0.052 (2)0.0152 (16)0.0173 (17)0.0038 (15)
C110.0285 (19)0.053 (2)0.072 (3)0.0135 (18)0.0101 (19)0.007 (2)
C120.050 (3)0.121 (5)0.080 (4)0.039 (3)0.007 (3)0.016 (3)
C130.041 (2)0.081 (3)0.101 (4)0.024 (2)0.036 (3)0.016 (3)
O30.0450 (19)0.063 (2)0.133 (4)0.0019 (17)0.016 (2)0.036 (2)
C140.045 (2)0.0291 (18)0.052 (2)0.0109 (16)0.0180 (17)0.0084 (15)
C150.050 (2)0.057 (3)0.068 (3)0.016 (2)0.034 (2)0.013 (2)
C160.078 (4)0.074 (4)0.083 (4)0.034 (3)0.032 (3)0.040 (3)
O40.063 (2)0.0432 (17)0.0675 (19)0.0048 (14)0.0292 (16)0.0091 (14)
Geometric parameters (Å, º) top
Cu1—C11.996 (3)C8—H8A0.9600
Cu1—C21.999 (3)C8—H8B0.9600
Cu1—Cl22.2639 (12)C8—H8C0.9600
Cu1—Cl12.2970 (13)O2—H20.8200
Cu1—Cu23.0333 (11)C9—C101.223 (5)
Cu2—C91.987 (4)C9—C111.501 (5)
Cu2—C102.003 (4)C10—C141.482 (5)
Cu2—Cl22.2642 (13)C11—O31.421 (5)
Cu2—Cl12.2852 (13)C11—C131.495 (7)
C1—C21.230 (5)C11—C121.530 (7)
C1—C31.493 (5)C12—H12A0.9600
C2—C61.490 (5)C12—H12B0.9600
C3—O11.444 (4)C12—H12C0.9600
C3—C41.511 (5)C13—H13A0.9600
C3—C51.522 (5)C13—H13B0.9600
C4—H4A0.9600C13—H13C0.9600
C4—H4B0.9600O3—H30.8200
C4—H4C0.9600C14—O41.428 (5)
C5—H5A0.9600C14—C151.515 (5)
C5—H5B0.9600C14—C161.520 (6)
C5—H5C0.9600C15—H15A0.9600
O1—H10.8200C15—H15B0.9600
C6—O21.438 (4)C15—H15C0.9600
C6—C71.512 (6)C16—H16B0.9600
C6—C81.518 (5)C16—H16A0.9600
C7—H7A0.9600C16—H16C0.9600
C7—H7B0.9600O4—H40.8200
C7—H7C0.9600
C1—Cu1—C235.85 (15)H7A—C7—H7B109.5
C1—Cu1—Cl2117.29 (11)C6—C7—H7C109.5
C2—Cu1—Cl2153.00 (11)H7A—C7—H7C109.5
C1—Cu1—Cl1145.28 (11)H7B—C7—H7C109.5
C2—Cu1—Cl1111.69 (11)C6—C8—H8A109.5
Cl2—Cu1—Cl195.01 (5)C6—C8—H8B109.5
C1—Cu1—Cu2154.50 (11)H8A—C8—H8B109.5
C2—Cu1—Cu2155.79 (11)C6—C8—H8C109.5
Cl2—Cu1—Cu247.95 (3)H8A—C8—H8C109.5
Cl1—Cu1—Cu248.38 (4)H8B—C8—H8C109.5
C9—Cu2—C1035.70 (15)C6—O2—H2109.5
C9—Cu2—Cl2155.37 (12)C10—C9—C11162.4 (4)
C10—Cu2—Cl2119.67 (12)C10—C9—Cu272.8 (2)
C9—Cu2—Cl1109.26 (12)C11—C9—Cu2124.7 (3)
C10—Cu2—Cl1144.87 (11)C9—C10—C14159.8 (4)
Cl2—Cu2—Cl195.33 (5)C9—C10—Cu271.5 (2)
C9—Cu2—Cu1156.13 (11)C14—C10—Cu2128.7 (3)
C10—Cu2—Cu1165.53 (11)O3—C11—C13111.7 (5)
Cl2—Cu2—Cu147.94 (4)O3—C11—C9109.3 (3)
Cl1—Cu2—Cu148.72 (3)C13—C11—C9110.5 (4)
Cu2—Cl1—Cu182.90 (4)O3—C11—C12105.9 (4)
Cu1—Cl2—Cu284.11 (5)C13—C11—C12112.1 (4)
C2—C1—C3161.2 (3)C9—C11—C12107.3 (4)
C2—C1—Cu172.2 (2)C11—C12—H12A109.5
C3—C1—Cu1126.5 (2)C11—C12—H12B109.5
C1—C2—C6162.9 (3)H12A—C12—H12B109.5
C1—C2—Cu171.9 (2)C11—C12—H12C109.5
C6—C2—Cu1125.1 (2)H12A—C12—H12C109.5
O1—C3—C1107.9 (3)H12B—C12—H12C109.5
O1—C3—C4106.7 (3)C11—C13—H13A109.5
C1—C3—C4110.6 (3)C11—C13—H13B109.5
O1—C3—C5109.2 (3)H13A—C13—H13B109.5
C1—C3—C5110.7 (3)C11—C13—H13C109.5
C4—C3—C5111.6 (3)H13A—C13—H13C109.5
C3—C4—H4A109.5H13B—C13—H13C109.5
C3—C4—H4B109.5C11—O3—H3109.5
H4A—C4—H4B109.5O4—C14—C10106.0 (3)
C3—C4—H4C109.5O4—C14—C15108.5 (3)
H4A—C4—H4C109.5C10—C14—C15111.8 (3)
H4B—C4—H4C109.5O4—C14—C16110.5 (4)
C3—C5—H5A109.5C10—C14—C16109.1 (4)
C3—C5—H5B109.5C15—C14—C16110.8 (4)
H5A—C5—H5B109.5C14—C15—H15A109.5
C3—C5—H5C109.5C14—C15—H15B109.5
H5A—C5—H5C109.5H15A—C15—H15B109.5
H5B—C5—H5C109.5C14—C15—H15C109.5
C3—O1—H1109.5H15A—C15—H15C109.5
O2—C6—C2107.7 (3)H15B—C15—H15C109.5
O2—C6—C7108.3 (3)C14—C16—H16B109.5
C2—C6—C7111.1 (3)C14—C16—H16A109.5
O2—C6—C8108.1 (3)H16B—C16—H16A109.5
C2—C6—C8109.5 (3)C14—C16—H16C109.5
C7—C6—C8112.0 (3)H16B—C16—H16C109.5
C6—C7—H7A109.5H16A—C16—H16C109.5
C6—C7—H7B109.5C14—O4—H4109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···Cl10.822.663.412 (7)154
O1—H1···O2i0.821.982.723 (6)150
O2—H2···O4ii0.821.912.725 (7)175
O4—H4···O1iii0.821.952.696 (6)152
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1, z; (iii) x, y1, z.
 

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