#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:58:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178708 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/19/4081943.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_4081943
loop_
_publ_author_name
'Zaitsev, Kirill V.'
'Kapranov, Andrey A.'
'Churakov, Andrei V.'
'Poleshchuk, Oleg Kh.'
'Oprunenko, Yuri F.'
'Tarasevich, Boris N.'
'Zaitseva, Galina S.'
'Karlov, Sergey S.'
_publ_section_title
;
 “Donor--Acceptor” Oligogermanes: Synthesis, Structure, and
 Electronic Properties
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              6500
_journal_paper_doi               10.1021/om4008218
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C54 H42 F10 Ge3'
_chemical_formula_sum            'C54 H42 F10 Ge3'
_chemical_formula_weight         1098.65
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.284(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.334(4)
_cell_length_b                   10.6788(19)
_cell_length_c                   21.741(4)
_cell_measurement_reflns_used    4827
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.433
_cell_measurement_theta_min      2.157
_cell_volume                     4692.5(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15821
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.986
_exptl_absorpt_correction_T_max  0.9248
_exptl_absorpt_correction_T_min  0.5038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.154
_refine_diff_density_min         -0.886
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1061P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                3614
_reflns_number_total             4338
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om4008218_si_002.cif
_cod_data_source_block           6
_cod_original_cell_volume        4692.6(14)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4081943
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ge1 Ge 0.5000 0.42433(4) 0.7500 0.02640(18) Uani 1 2 d S
Ge2 Ge 0.565368(18) 0.31640(3) 0.677390(18) 0.02573(16) Uani 1 1 d .
F12 F 0.64015(11) 0.3864(2) 0.81878(11) 0.0417(6) Uani 1 1 d .
F13 F 0.71060(13) 0.5191(3) 0.90824(12) 0.0567(7) Uani 1 1 d .
F14 F 0.66146(15) 0.7382(3) 0.94826(13) 0.0630(8) Uani 1 1 d .
F15 F 0.54194(14) 0.8212(2) 0.89804(14) 0.0573(8) Uani 1 1 d .
F16 F 0.47157(12) 0.69075(19) 0.80842(13) 0.0486(7) Uani 1 1 d .
C11 C 0.55419(18) 0.5340(3) 0.80992(18) 0.0313(8) Uani 1 1 d .
C12 C 0.6145(2) 0.4952(3) 0.83741(19) 0.0353(9) Uani 1 1 d .
C13 C 0.6512(2) 0.5601(4) 0.8838(2) 0.0404(10) Uani 1 1 d .
C14 C 0.6266(2) 0.6702(4) 0.9044(2) 0.0463(11) Uani 1 1 d .
C15 C 0.5661(2) 0.7129(4) 0.8786(2) 0.0434(11) Uani 1 1 d .
C16 C 0.5307(2) 0.6452(3) 0.8322(2) 0.0359(9) Uani 1 1 d .
C21 C 0.50599(17) 0.2669(3) 0.60453(17) 0.0273(8) Uani 1 1 d .
C22 C 0.48055(19) 0.3535(3) 0.56022(19) 0.0337(9) Uani 1 1 d .
H22A H 0.4899 0.4399 0.5669 0.040 Uiso 1 1 calc R
C23 C 0.4424(2) 0.3173(3) 0.5073(2) 0.0366(10) Uani 1 1 d .
H23A H 0.4254 0.3790 0.4783 0.044 Uiso 1 1 calc R
C24 C 0.42804(18) 0.1912(3) 0.49526(19) 0.0334(9) Uani 1 1 d .
C25 C 0.45292(18) 0.1045(3) 0.53951(19) 0.0325(9) Uani 1 1 d .
H25A H 0.4436 0.0181 0.5328 0.039 Uiso 1 1 calc R
C26 C 0.49084(17) 0.1410(3) 0.59293(17) 0.0285(8) Uani 1 1 d .
H26A H 0.5069 0.0795 0.6224 0.034 Uiso 1 1 calc R
C27 C 0.3877(2) 0.1505(4) 0.4370(2) 0.0452(10) Uani 1 1 d .
H27A H 0.4088 0.1797 0.4012 0.068 Uiso 1 1 calc R
H27B H 0.3432 0.1862 0.4356 0.068 Uiso 1 1 calc R
H27C H 0.3848 0.0589 0.4361 0.068 Uiso 1 1 calc R
C31 C 0.60825(17) 0.1662(3) 0.71339(17) 0.0262(8) Uani 1 1 d .
C32 C 0.5911(2) 0.1131(4) 0.76703(19) 0.0387(10) Uani 1 1 d .
H32A H 0.5584 0.1522 0.7885 0.046 Uiso 1 1 calc R
C33 C 0.6207(2) 0.0032(4) 0.7902(2) 0.0423(10) Uani 1 1 d .
H33A H 0.6083 -0.0311 0.8276 0.051 Uiso 1 1 calc R
C34 C 0.66786(18) -0.0571(3) 0.76018(18) 0.0302(8) Uani 1 1 d .
C35 C 0.68519(18) -0.0034(3) 0.70631(19) 0.0334(9) Uani 1 1 d .
H35A H 0.7178 -0.0429 0.6849 0.040 Uiso 1 1 calc R
C36 C 0.65622(18) 0.1059(3) 0.68302(19) 0.0322(8) Uani 1 1 d .
H36A H 0.6691 0.1405 0.6459 0.039 Uiso 1 1 calc R
C37 C 0.7004(2) -0.1751(3) 0.7860(2) 0.0412(10) Uani 1 1 d .
H37A H 0.7412 -0.1898 0.7669 0.062 Uiso 1 1 calc R
H37B H 0.6702 -0.2460 0.7771 0.062 Uiso 1 1 calc R
H37C H 0.7110 -0.1665 0.8309 0.062 Uiso 1 1 calc R
C41 C 0.63048(18) 0.4279(3) 0.64569(19) 0.0294(8) Uani 1 1 d .
C42 C 0.65196(19) 0.3989(3) 0.58981(19) 0.0350(9) Uani 1 1 d .
H42A H 0.6324 0.3306 0.5665 0.042 Uiso 1 1 calc R
C43 C 0.7018(2) 0.4676(4) 0.56651(19) 0.0400(10) Uani 1 1 d .
H43A H 0.7164 0.4445 0.5280 0.048 Uiso 1 1 calc R
C44 C 0.73047(19) 0.5694(4) 0.5989(2) 0.0393(10) Uani 1 1 d .
C45 C 0.7084(2) 0.5982(4) 0.6546(2) 0.0388(10) Uani 1 1 d .
H45A H 0.7272 0.6677 0.6775 0.047 Uiso 1 1 calc R
C46 C 0.65935(19) 0.5286(3) 0.67882(19) 0.0336(9) Uani 1 1 d .
H46A H 0.6457 0.5500 0.7179 0.040 Uiso 1 1 calc R
C47 C 0.7843(2) 0.6455(5) 0.5745(3) 0.0591(13) Uani 1 1 d .
H47A H 0.8169 0.6702 0.6089 0.089 Uiso 1 1 calc R
H47B H 0.7650 0.7205 0.5537 0.089 Uiso 1 1 calc R
H47C H 0.8061 0.5951 0.5449 0.089 Uiso 1 1 calc R
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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C11 Ge1 C11 108.0(2) . 2_656
C11 Ge1 Ge2 113.34(10) . .
C11 Ge1 Ge2 98.91(10) 2_656 .
C11 Ge1 Ge2 98.91(10) . 2_656
C11 Ge1 Ge2 113.34(10) 2_656 2_656
Ge2 Ge1 Ge2 124.10(3) . 2_656
C31 Ge2 C21 108.17(15) . .
C31 Ge2 C41 110.58(14) . .
C21 Ge2 C41 105.09(16) . .
C31 Ge2 Ge1 112.19(11) . .
C21 Ge2 Ge1 108.51(10) . .
C41 Ge2 Ge1 111.96(10) . .
C12 C11 C16 115.7(4) . .
C12 C11 Ge1 120.8(3) . .
C16 C11 Ge1 123.0(3) . .
F12 C12 C11 119.0(3) . .
F12 C12 C13 117.2(4) . .
C11 C12 C13 123.8(4) . .
F13 C13 C14 119.7(4) . .
F13 C13 C12 121.4(4) . .
C14 C13 C12 118.9(4) . .
F14 C14 C13 120.9(5) . .
F14 C14 C15 119.5(4) . .
C13 C14 C15 119.5(4) . .
F15 C15 C14 119.9(4) . .
F15 C15 C16 120.2(4) . .
C14 C15 C16 119.9(4) . .
F16 C16 C15 117.7(3) . .
F16 C16 C11 120.2(4) . .
C15 C16 C11 122.2(4) . .
C22 C21 C26 117.2(4) . .
C22 C21 Ge2 122.0(3) . .
C26 C21 Ge2 120.7(3) . .
C23 C22 C21 121.7(3) . .
C23 C22 H22A 119.2 . .
C21 C22 H22A 119.2 . .
C22 C23 C24 121.1(4) . .
C22 C23 H23A 119.4 . .
C24 C23 H23A 119.4 . .
C25 C24 C23 117.4(4) . .
C25 C24 C27 121.1(3) . .
C23 C24 C27 121.5(4) . .
C26 C25 C24 121.5(3) . .
C26 C25 H25A 119.3 . .
C24 C25 H25A 119.3 . .
C25 C26 C21 121.1(3) . .
C25 C26 H26A 119.4 . .
C21 C26 H26A 119.4 . .
C24 C27 H27A 109.5 . .
C24 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C24 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C32 C31 C36 117.8(3) . .
C32 C31 Ge2 122.4(3) . .
C36 C31 Ge2 119.7(3) . .
C31 C32 C33 121.0(3) . .
C31 C32 H32A 119.5 . .
C33 C32 H32A 119.5 . .
C34 C33 C32 121.3(4) . .
C34 C33 H33A 119.3 . .
C32 C33 H33A 119.3 . .
C33 C34 C35 117.6(3) . .
C33 C34 C37 121.0(4) . .
C35 C34 C37 121.4(3) . .
C36 C35 C34 121.6(3) . .
C36 C35 H35A 119.2 . .
C34 C35 H35A 119.2 . .
C35 C36 C31 120.7(3) . .
C35 C36 H36A 119.7 . .
C31 C36 H36A 119.7 . .
C34 C37 H37A 109.5 . .
C34 C37 H37B 109.5 . .
H37A C37 H37B 109.5 . .
C34 C37 H37C 109.5 . .
H37A C37 H37C 109.5 . .
H37B C37 H37C 109.5 . .
C42 C41 C46 118.5(3) . .
C42 C41 Ge2 117.8(3) . .
C46 C41 Ge2 123.5(3) . .
C41 C42 C43 121.3(4) . .
C41 C42 H42A 119.4 . .
C43 C42 H42A 119.4 . .
C44 C43 C42 120.7(4) . .
C44 C43 H43A 119.6 . .
C42 C43 H43A 119.6 . .
C45 C44 C43 117.6(3) . .
C45 C44 C47 120.7(4) . .
C43 C44 C47 121.7(4) . .
C44 C45 C46 122.1(4) . .
C44 C45 H45A 119.0 . .
C46 C45 H45A 119.0 . .
C41 C46 C45 119.8(4) . .
C41 C46 H46A 120.1 . .
C45 C46 H46A 120.1 . .
C44 C47 H47A 109.5 . .
C44 C47 H47B 109.5 . .
H47A C47 H47B 109.5 . .
C44 C47 H47C 109.5 . .
H47A C47 H47C 109.5 . .
H47B C47 H47C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 C11 1.992(4) .
Ge1 C11 1.992(4) 2_656
Ge1 Ge2 2.4590(5) .
Ge1 Ge2 2.4590(5) 2_656
Ge2 C31 1.949(3) .
Ge2 C21 1.957(4) .
Ge2 C41 1.961(3) .
F12 C12 1.353(4) .
F13 C13 1.339(5) .
F14 C14 1.338(5) .
F15 C15 1.342(4) .
F16 C16 1.346(5) .
C11 C12 1.369(6) .
C11 C16 1.387(5) .
C12 C13 1.374(6) .
C13 C14 1.373(6) .
C14 C15 1.374(7) .
C15 C16 1.378(6) .
C21 C22 1.394(5) .
C21 C26 1.395(5) .
C22 C23 1.371(6) .
C22 H22A 0.9500 .
C23 C24 1.396(5) .
C23 H23A 0.9500 .
C24 C25 1.390(6) .
C24 C27 1.496(6) .
C25 C26 1.378(5) .
C25 H25A 0.9500 .
C26 H26A 0.9500 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C31 C32 1.376(5) .
C31 C36 1.394(5) .
C32 C33 1.389(6) .
C32 H32A 0.9500 .
C33 C34 1.378(5) .
C33 H33A 0.9500 .
C34 C35 1.384(5) .
C34 C37 1.503(5) .
C35 C36 1.379(5) .
C35 H35A 0.9500 .
C36 H36A 0.9500 .
C37 H37A 0.9800 .
C37 H37B 0.9800 .
C37 H37C 0.9800 .
C41 C42 1.371(5) .
C41 C46 1.388(5) .
C42 C43 1.391(5) .
C42 H42A 0.9500 .
C43 C44 1.388(6) .
C43 H43A 0.9500 .
C44 C45 1.373(6) .
C44 C47 1.505(5) .
C45 C46 1.393(5) .
C45 H45A 0.9500 .
C46 H46A 0.9500 .
C47 H47A 0.9800 .
C47 H47B 0.9800 .
C47 H47C 0.9800 .
