#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/27/2212761.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2212761
loop_
_publ_author_name
'Imhof, Wolfgang'
'Schmidt, Andreas'
'Walther, Dirk'
_publ_section_title
;
 Di-μ-chlorido-bis{[(3,4-η)-2,5-dimethylhex-3-yne-2,5-diol]copper(I)}
;
_journal_coeditor_code           BG2029
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m968
_journal_page_last               m970
_journal_paper_doi               10.1107/S1600536807009580
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu2 Cl2 (C8 H14 O2)2]'
_chemical_formula_moiety         'C16 H28 Cl2 Cu2 O4'
_chemical_formula_sum            'C16 H28 Cl2 Cu2 O4'
_chemical_formula_weight         482.36
_chemical_name_systematic
;
Di-μ-chloro-bis[(3,4-η)-(2,5-dimethylhex-3-yne-2,5-diol)copper(I)]
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                92.11(3)
_cell_angle_beta                 112.13(3)
_cell_angle_gamma                101.39(3)
_cell_formula_units_Z            2
_cell_length_a                   8.981(2)
_cell_length_b                   11.056(2)
_cell_length_c                   11.676(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4
_cell_measurement_theta_min      16.9
_cell_volume                     1044.9(5)
_computing_cell_refinement       'SET4 (Boer et al., 1984)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'XP (Siemens, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3859
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_time  600
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.306
_exptl_absorpt_correction_T_max  0.68
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.217
_refine_diff_density_min         -1.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3666
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0904P)²+0.5653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                3102
_reflns_number_total             3666
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2029.cif
_cod_data_source_block           I
_cod_original_cell_volume        1044.9(3)
_cod_database_code               2212761
_cod_database_fobs_code          2212761
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cu Cu1 0.14223(6) 0.14132(4) 0.64959(5) 0.0478(2) Uani d . 1
Cu Cu2 0.26375(6) -0.08200(4) 0.76057(5) 0.0496(2) Uani d . 1
Cl Cl1 0.39491(13) 0.09160(10) 0.70668(14) 0.0664(4) Uani d . 1
Cl Cl2 0.00668(12) -0.04989(9) 0.66288(12) 0.0557(3) Uani d . 1
C C1 0.0253(4) 0.2793(3) 0.6364(3) 0.0351(7) Uani d . 1
C C2 0.1577(4) 0.3213(3) 0.6281(3) 0.0343(7) Uani d . 1
C C3 -0.1380(4) 0.2718(3) 0.6450(3) 0.0365(8) Uani d . 1
C C4 -0.1321(5) 0.2346(5) 0.7696(4) 0.0558(11) Uani d . 1
H H4A -0.0503 0.2956 0.8350 0.084 Uiso calc R 1
H H4B -0.1042 0.1551 0.7797 0.084 Uiso calc R 1
H H4C -0.2382 0.2296 0.7733 0.084 Uiso calc R 1
C C5 -0.2747(5) 0.1831(4) 0.5375(4) 0.0539(10) Uani d . 1
H H5A -0.2833 0.2144 0.4602 0.081 Uiso calc R 1
H H5B -0.3775 0.1762 0.5470 0.081 Uiso calc R 1
H H5C -0.2493 0.1027 0.5375 0.081 Uiso calc R 1
O O1 -0.1704(3) 0.3947(2) 0.6389(3) 0.0488(7) Uani d D 1
H H1 -0.1587 0.4229 0.5781 0.083 Uiso calc RD 1
C C6 0.2971(5) 0.4057(3) 0.6109(3) 0.0373(8) Uani d . 1
C C7 0.4546(5) 0.4247(4) 0.7263(4) 0.0557(11) Uani d . 1
H H7A 0.4337 0.4478 0.7980 0.084 Uiso calc R 1
H H7B 0.5375 0.4895 0.7184 0.084 Uiso calc R 1
H H7C 0.4925 0.3490 0.7359 0.084 Uiso calc R 1
C C8 0.3169(5) 0.3544(4) 0.4963(4) 0.0489(10) Uani d . 1
H H8A 0.4016 0.4117 0.4819 0.073 Uiso calc R 1
H H8B 0.2145 0.3433 0.4253 0.073 Uiso calc R 1
H H8C 0.3471 0.2759 0.5092 0.073 Uiso calc R 1
O O2 0.2552(4) 0.5242(3) 0.5895(3) 0.0595(8) Uani d D 1
H H2 0.2099 0.5408 0.6354 0.101 Uiso calc RD 1
C C9 0.4294(4) -0.1741(3) 0.8578(4) 0.0416(9) Uani d . 1
C C10 0.2934(5) -0.2356(3) 0.8441(4) 0.0396(8) Uani d . 1
C C11 0.6122(5) -0.1322(4) 0.8937(4) 0.0538(11) Uani d . 1
C C12 0.6951(7) -0.2134(7) 0.9904(5) 0.0857(18) Uani d . 1
H H12A 0.8122 -0.1795 1.0268 0.129 Uiso calc R 1
H H12B 0.6732 -0.2963 0.9508 0.129 Uiso calc R 1
H H12C 0.6521 -0.2153 1.0543 0.129 Uiso calc R 1
C C13 0.6534(6) -0.1416(5) 0.7814(5) 0.0701(14) Uani d . 1
H H13A 0.7697 -0.1098 0.8051 0.105 Uiso calc R 1
H H13B 0.5932 -0.0941 0.7208 0.105 Uiso calc R 1
H H13C 0.6237 -0.2271 0.7464 0.105 Uiso calc R 1
O O3 0.6677(4) -0.0089(3) 0.9558(4) 0.0895(14) Uani d D 1
H H3 0.6246 0.0382 0.9077 0.152 Uiso calc RD 1
C C14 0.1655(5) -0.3394(3) 0.8508(4) 0.0420(8) Uani d . 1
C C15 0.0300(5) -0.2931(4) 0.8737(4) 0.0545(11) Uani d . 1
H H15A 0.0768 -0.2388 0.9507 0.082 Uiso calc R 1
H H15B -0.0499 -0.3626 0.8782 0.082 Uiso calc R 1
H H15C -0.0228 -0.2486 0.8066 0.082 Uiso calc R 1
C C16 0.2469(7) -0.4151(5) 0.9527(5) 0.0749(15) Uani d . 1
H H16B 0.3304 -0.4452 0.9355 0.112 Uiso calc R 1
H H16A 0.1652 -0.4842 0.9556 0.112 Uiso calc R 1
H H16C 0.2964 -0.3636 1.0316 0.112 Uiso calc R 1
O O4 0.0951(4) -0.4130(3) 0.7320(3) 0.0599(8) Uani d D 1
H H4 0.0137 -0.4652 0.7274 0.102 Uiso calc RD 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 Cu1 C2 35.85(15) ?
C1 Cu1 Cl2 117.29(11) ?
C2 Cu1 Cl2 153.00(11) ?
C1 Cu1 Cl1 145.28(11) ?
C2 Cu1 Cl1 111.69(11) ?
Cl2 Cu1 Cl1 95.01(5) y
C1 Cu1 Cu2 154.50(11) ?
C2 Cu1 Cu2 155.79(11) ?
Cl2 Cu1 Cu2 47.95(3) ?
Cl1 Cu1 Cu2 48.38(4) ?
C9 Cu2 C10 35.70(15) ?
C9 Cu2 Cl2 155.37(12) ?
C10 Cu2 Cl2 119.67(12) ?
C9 Cu2 Cl1 109.26(12) ?
C10 Cu2 Cl1 144.87(11) ?
Cl2 Cu2 Cl1 95.33(5) y
C9 Cu2 Cu1 156.13(11) ?
C10 Cu2 Cu1 165.53(11) ?
Cl2 Cu2 Cu1 47.94(4) ?
Cl1 Cu2 Cu1 48.72(3) ?
Cu2 Cl1 Cu1 82.90(4) ?
Cu1 Cl2 Cu2 84.11(5) ?
C2 C1 C3 161.2(3) ?
C2 C1 Cu1 72.2(2) ?
C3 C1 Cu1 126.5(2) ?
C1 C2 C6 162.9(3) ?
C1 C2 Cu1 71.9(2) ?
C6 C2 Cu1 125.1(2) ?
O1 C3 C1 107.9(3) ?
O1 C3 C4 106.7(3) ?
C1 C3 C4 110.6(3) ?
O1 C3 C5 109.2(3) ?
C1 C3 C5 110.7(3) ?
C4 C3 C5 111.6(3) ?
C3 C4 H4A 109.5 ?
C3 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
C3 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
C3 C5 H5A 109.5 ?
C3 C5 H5B 109.5 ?
H5A C5 H5B 109.5 ?
C3 C5 H5C 109.5 ?
H5A C5 H5C 109.5 ?
H5B C5 H5C 109.5 ?
C3 O1 H1 109.5 ?
O2 C6 C2 107.7(3) ?
O2 C6 C7 108.3(3) ?
C2 C6 C7 111.1(3) ?
O2 C6 C8 108.1(3) ?
C2 C6 C8 109.5(3) ?
C7 C6 C8 112.0(3) ?
C6 C7 H7A 109.5 ?
C6 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C6 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C6 C8 H8A 109.5 ?
C6 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C6 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C6 O2 H2 109.5 ?
C10 C9 C11 162.4(4) ?
C10 C9 Cu2 72.8(2) ?
C11 C9 Cu2 124.7(3) ?
C9 C10 C14 159.8(4) ?
C9 C10 Cu2 71.5(2) ?
C14 C10 Cu2 128.7(3) ?
O3 C11 C13 111.7(5) ?
O3 C11 C9 109.3(3) ?
C13 C11 C9 110.5(4) ?
O3 C11 C12 105.9(4) ?
C13 C11 C12 112.1(4) ?
C9 C11 C12 107.3(4) ?
C11 C12 H12A 109.5 ?
C11 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C11 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C11 C13 H13A 109.5 ?
C11 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C11 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C11 O3 H3 109.5 ?
O4 C14 C10 106.0(3) ?
O4 C14 C15 108.5(3) ?
C10 C14 C15 111.8(3) ?
O4 C14 C16 110.5(4) ?
C10 C14 C16 109.1(4) ?
C15 C14 C16 110.8(4) ?
C14 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C14 C16 H16B 109.5 ?
C14 C16 H16A 109.5 ?
H16B C16 H16A 109.5 ?
C14 C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
C14 O4 H4 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 C1 1.996(3) y
Cu1 C2 1.999(3) y
Cu1 Cl2 2.2639(12) y
Cu1 Cl1 2.2970(13) y
Cu1 Cu2 3.0333(11) ?
Cu2 C9 1.987(4) y
Cu2 C10 2.003(4) y
Cu2 Cl2 2.2642(13) y
Cu2 Cl1 2.2852(13) y
C1 C2 1.230(5) ?
C1 C3 1.493(5) ?
C2 C6 1.490(5) ?
C3 O1 1.444(4) ?
C3 C4 1.511(5) ?
C3 C5 1.522(5) ?
C4 H4A 0.9600 ?
C4 H4B 0.9600 ?
C4 H4C 0.9600 ?
C5 H5A 0.9600 ?
C5 H5B 0.9600 ?
C5 H5C 0.9600 ?
O1 H1 0.8200 ?
C6 O2 1.438(4) ?
C6 C7 1.512(6) ?
C6 C8 1.518(5) ?
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 0.9600 ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
O2 H2 0.8200 ?
C9 C10 1.223(5) ?
C9 C11 1.501(5) ?
C10 C14 1.482(5) ?
C11 O3 1.421(5) ?
C11 C13 1.495(7) ?
C11 C12 1.530(7) ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
O3 H3 0.8200 ?
C14 O4 1.428(5) ?
C14 C15 1.515(5) ?
C14 C16 1.520(6) ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 H16B 0.9600 ?
C16 H16A 0.9600 ?
C16 H16C 0.9600 ?
O4 H4 0.8200 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 Cl1 1_555 0.82 2.655 3.412(7) 154
O1 H1 O2 2_566 0.82 1.983 2.723(6) 150
O2 H2 O4 1_565 0.82 1.907 2.725(7) 175
O4 H4 O1 1_545 0.82 1.946 2.696(6) 152
