#------------------------------------------------------------------------------
#$Date: 2016-08-05 06:34:19 +0300 (Fri, 05 Aug 2016) $
#$Revision: 184945 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/65/4086588.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4086588
loop_
_publ_author_name
'Zhang, Fei-Bao'
'Adachi, Yohei'
'Ooyama, Yousuke'
'Ohshita, Joji'
_publ_section_title
;
 Synthesis and Properties of Benzofuran-Fused Silole and Germole
 Derivatives: Reversible Dimerization and Crystal Structures of Monomers
 and Dimers
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              2327
_journal_paper_doi               10.1021/acs.organomet.6b00222
_journal_volume                  35
_journal_year                    2016
_chemical_formula_sum            'C56 H36 Ge2 O4'
_chemical_formula_weight         918.03
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                98.300(2)
_cell_angle_beta                 106.103(2)
_cell_angle_gamma                99.866(2)
_cell_formula_units_Z            1
_cell_length_a                   9.7837(15)
_cell_length_b                   10.8094(16)
_cell_length_c                   10.8576(16)
_cell_measurement_reflns_used    8772
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      27.9591
_cell_measurement_theta_min      2.4836
_cell_volume                     1064.3(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2(Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1(Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'multilayered conforcal mirror'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10542
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.95
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'
_exptl_absorpt_coefficient_mu    1.462
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0221
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0245P)²+0.9785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0568
_reflns_number_gt                3607
_reflns_number_total             3753
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00222_si_003.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4086587--4086590.cif.'
_cod_database_code               4086588
loop_
_space_group_symop_operation_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_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
Ge Ge1 0.61110(2) 0.66318(2) 0.35758(2) 0.01020(7) Uani d . . 1
O O1 0.80309(13) 0.69065(11) 0.74077(11) 0.0134(2) Uani d . . 1
O O2 0.69283(13) 0.42315(11) 0.59100(11) 0.0137(3) Uani d . . 1
C C10 0.53919(18) 0.50123(15) 0.41264(16) 0.0108(3) Uani d . . 1
C C1 0.88228(18) 0.81123(16) 0.74454(17) 0.0130(3) Uani d . . 1
C C17 0.47423(18) 0.76191(17) 0.28209(17) 0.0134(3) Uani d . . 1
C C8 0.72909(18) 0.73704(16) 0.53659(16) 0.0123(3) Uani d . . 1
C C23 0.73142(18) 0.63465(16) 0.24492(17) 0.0141(3) Uani d . . 1
C C7 0.71367(18) 0.65068(16) 0.61325(16) 0.0119(3) Uani d . . 1
C C5 0.90673(19) 0.96531(17) 0.60832(17) 0.0156(4) Uani d . . 1
H H5 0.8792 0.9922 0.5272 0.019 Uiso calc U R 1
C C9 0.61348(18) 0.52286(16) 0.56448(16) 0.0114(3) Uani d . . 1
C C2 0.98938(19) 0.88772(17) 0.85284(17) 0.0164(4) Uani d . . 1
H H2 1.0162 0.8613 0.9343 0.02 Uiso calc U R 1
C C13 0.59141(18) 0.38605(16) 0.36442(17) 0.0134(3) Uani d . . 1
C C22 0.36411(19) 0.71098(18) 0.16269(18) 0.0186(4) Uani d . . 1
H H22 0.35 0.6239 0.1218 0.022 Uiso calc U R 1
C C18 0.4922(2) 0.88935(18) 0.34096(18) 0.0182(4) Uani d . . 1
H H18 0.5663 0.925 0.4221 0.022 Uiso calc U R 1
C C12 0.67943(19) 0.34928(17) 0.47131(17) 0.0149(4) Uani d . . 1
C C6 0.84007(18) 0.84535(16) 0.62176(16) 0.0130(3) Uani d . . 1
C C27 0.8589(2) 0.59003(19) 0.2889(2) 0.0229(4) Uani d . . 1
H H27 0.8849 0.5693 0.3732 0.027 Uiso calc U R 1
C C4 1.0141(2) 1.04452(17) 0.71600(18) 0.0179(4) Uani d . . 1
H H4 1.0601 1.1266 0.7082 0.022 Uiso calc U R 1
C C24 0.6950(2) 0.66313(18) 0.12044(18) 0.0185(4) Uani d . . 1
H H24 0.6087 0.6934 0.0892 0.022 Uiso calc U R 1
C C11 0.7500(2) 0.24969(18) 0.45860(19) 0.0200(4) Uani d . . 1
H H11 0.8087 0.2257 0.533 0.024 Uiso calc U R 1
C C14 0.5729(2) 0.32046(17) 0.23882(18) 0.0183(4) Uani d . . 1
H H14 0.5131 0.3436 0.1645 0.022 Uiso calc U R 1
C C3 1.0558(2) 1.00577(18) 0.83578(18) 0.0189(4) Uani d . . 1
H H3 1.1313 1.0613 0.9072 0.023 Uiso calc U R 1
C C15 0.6435(2) 0.22011(19) 0.2236(2) 0.0240(4) Uani d . . 1
H H15 0.6314 0.1745 0.1383 0.029 Uiso calc U R 1
C C20 0.2950(2) 0.9140(2) 0.1637(2) 0.0245(4) Uani d . . 1
H H20 0.2341 0.966 0.1233 0.029 Uiso calc U R 1
C C19 0.4025(2) 0.96496(19) 0.2817(2) 0.0227(4) Uani d . . 1
H H19 0.4153 1.0518 0.3227 0.027 Uiso calc U R 1
C C16 0.7312(2) 0.18650(19) 0.3323(2) 0.0248(4) Uani d . . 1
H H16 0.7794 0.1187 0.3199 0.03 Uiso calc U R 1
C C21 0.2755(2) 0.78694(19) 0.10375(19) 0.0232(4) Uani d . . 1
H H21 0.2014 0.7521 0.0224 0.028 Uiso calc U R 1
C C26 0.9091(2) 0.60593(19) 0.0861(2) 0.0275(5) Uani d . . 1
H H26 0.9702 0.5973 0.0324 0.033 Uiso calc U R 1
C C00U 0.9480(2) 0.5758(2) 0.2099(2) 0.0295(5) Uani d . . 1
H H00U 1.0346 0.5459 0.2402 0.035 Uiso calc U R 1
C C25 0.7835(2) 0.64777(19) 0.04131(19) 0.0252(4) Uani d . . 1
H H25 0.7567 0.6663 -0.0439 0.03 Uiso calc U R 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'
Ge Ge 0.1547 1.8001 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C8 Ge1 C17 . . 114.25(7)
C8 Ge1 C23 . . 111.51(7)
C17 Ge1 C23 . . 108.97(7)
C8 Ge1 C10 . . 89.93(7)
C17 Ge1 C10 . . 119.75(7)
C23 Ge1 C10 . . 111.30(7)
C7 O1 C1 . . 104.39(13)
C12 O2 C9 . . 107.05(12)
C13 C10 C9 . 2_666 117.61(14)
C13 C10 C9 . . 101.29(13)
C9 C10 C9 2_666 . 89.03(12)
C13 C10 Ge1 . . 115.46(11)
C9 C10 Ge1 2_666 . 119.69(11)
C9 C10 Ge1 . . 106.75(11)
C2 C1 O1 . . 125.22(15)
C2 C1 C6 . . 124.04(16)
O1 C1 C6 . . 110.73(14)
C18 C17 C22 . . 118.93(16)
C18 C17 Ge1 . . 119.77(13)
C22 C17 Ge1 . . 121.07(13)
C7 C8 C6 . . 105.10(15)
C7 C8 Ge1 . . 109.75(12)
C6 C8 Ge1 . . 144.78(13)
C24 C23 C27 . . 118.64(17)
C24 C23 Ge1 . . 120.42(13)
C27 C23 Ge1 . . 120.89(14)
C8 C7 O1 . . 114.03(15)
C8 C7 C9 . . 123.44(15)
O1 C7 C9 . . 122.50(14)
C4 C5 C6 . . 118.58(16)
C4 C5 H5 . . 120.7
C6 C5 H5 . . 120.7
O2 C9 C7 . . 110.37(13)
O2 C9 C10 . 2_666 114.28(13)
C7 C9 C10 . 2_666 120.43(14)
O2 C9 C10 . . 108.55(13)
C7 C9 C10 . . 110.03(13)
C10 C9 C10 2_666 . 90.97(13)
C1 C2 C3 . . 116.10(16)
C1 C2 H2 . . 121.9
C3 C2 H2 . . 121.9
C14 C13 C12 . . 119.01(16)
C14 C13 C10 . . 131.83(16)
C12 C13 C10 . . 109.06(15)
C21 C22 C17 . . 120.36(17)
C21 C22 H22 . . 119.8
C17 C22 H22 . . 119.8
C17 C18 C19 . . 120.48(17)
C17 C18 H18 . . 119.8
C19 C18 H18 . . 119.8
C11 C12 O2 . . 123.03(16)
C11 C12 C13 . . 122.99(17)
O2 C12 C13 . . 113.97(15)
C5 C6 C1 . . 118.53(16)
C5 C6 C8 . . 135.73(16)
C1 C6 C8 . . 105.74(15)
C00U C27 C23 . . 120.42(19)
C00U C27 H27 . . 119.8
C23 C27 H27 . . 119.8
C5 C4 C3 . . 121.21(17)
C5 C4 H4 . . 119.4
C3 C4 H4 . . 119.4
C25 C24 C23 . . 120.77(18)
C25 C24 H24 . . 119.6
C23 C24 H24 . . 119.6
C12 C11 C16 . . 117.00(17)
C12 C11 H11 . . 121.5
C16 C11 H11 . . 121.5
C13 C14 C15 . . 119.00(17)
C13 C14 H14 . . 120.5
C15 C14 H14 . . 120.5
C2 C3 C4 . . 121.51(17)
C2 C3 H3 . . 119.2
C4 C3 H3 . . 119.2
C16 C15 C14 . . 120.49(18)
C16 C15 H15 . . 119.8
C14 C15 H15 . . 119.8
C19 C20 C21 . . 120.12(17)
C19 C20 H20 . . 119.9
C21 C20 H20 . . 119.9
C20 C19 C18 . . 120.10(18)
C20 C19 H19 . . 119.9
C18 C19 H19 . . 119.9
C11 C16 C15 . . 121.50(17)
C11 C16 H16 . . 119.2
C15 C16 H16 . . 119.2
C20 C21 C22 . . 120.01(18)
C20 C21 H21 . . 120.0
C22 C21 H21 . . 120.0
C25 C26 C00U . . 120.49(18)
C25 C26 H26 . . 119.8
C00U C26 H26 . . 119.8
C27 C00U C26 . . 119.58(19)
C27 C00U H00U . . 120.2
C26 C00U H00U . . 120.2
C26 C25 C24 . . 120.08(19)
C26 C25 H25 . . 120.0
C24 C25 H25 . . 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ge1 C8 . 1.9336(17)
Ge1 C17 . 1.9332(17)
Ge1 C23 . 1.9471(17)
Ge1 C10 . 2.0076(16)
O1 C7 . 1.377(2)
O1 C1 . 1.386(2)
O2 C12 . 1.383(2)
O2 C9 . 1.449(2)
C10 C13 . 1.504(2)
C10 C9 2_666 1.566(2)
C10 C9 . 1.570(2)
C1 C2 . 1.380(2)
C1 C6 . 1.404(2)
C17 C18 . 1.392(3)
C17 C22 . 1.400(2)
C8 C7 . 1.354(2)
C8 C6 . 1.449(2)
C23 C24 . 1.392(3)
C23 C27 . 1.400(3)
C7 C9 . 1.479(2)
C5 C4 . 1.387(3)
C5 C6 . 1.395(2)
C5 H5 . 0.95
C9 C10 2_666 1.566(2)
C2 C3 . 1.391(3)
C2 H2 . 0.95
C13 C14 . 1.391(2)
C13 C12 . 1.394(2)
C22 C21 . 1.387(3)
C22 H22 . 0.95
C18 C19 . 1.392(3)
C18 H18 . 0.95
C12 C11 . 1.386(3)
C27 C00U . 1.393(3)
C27 H27 . 0.95
C4 C3 . 1.398(3)
C4 H4 . 0.95
C24 C25 . 1.391(3)
C24 H24 . 0.95
C11 C16 . 1.388(3)
C11 H11 . 0.95
C14 C15 . 1.396(3)
C14 H14 . 0.95
C3 H3 . 0.95
C15 C16 . 1.389(3)
C15 H15 . 0.95
C20 C19 . 1.379(3)
C20 C21 . 1.390(3)
C20 H20 . 0.95
C19 H19 . 0.95
C16 H16 . 0.95
C21 H21 . 0.95
C26 C25 . 1.369(3)
C26 C00U . 1.393(3)
C26 H26 . 0.95
C00U H00U . 0.95
C25 H25 . 0.95
