#------------------------------------------------------------------------------
#$Date: 2025-08-20 16:37:07 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301831 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/91/4089146.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_4089146
loop_
_publ_author_name
'Zaitsev, Kirill V.'
'Lam, Kevin'
'Zhanabil, Zhaisan'
'Suleimen, Yerlan'
'Kharcheva, Anastasia V.'
'Tafeenko, Viktor A.'
'Oprunenko, Yuri F.'
'Poleshchuk, Oleg Kh.'
'Lermontova, Elmira Kh.'
'Churakov, Andrei V.'
_publ_section_title
;
 Oligogermanes Containing Only Electron-Withdrawing Substituents:
 Synthesis and Properties
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              298
_journal_paper_doi               10.1021/acs.organomet.6b00767
_journal_volume                  36
_journal_year                    2016
_chemical_formula_moiety         'C54 H24 F28 Ge3'
_chemical_formula_sum            'C54 H24 F28 Ge3'
_chemical_formula_weight         1422.50
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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                 96.599(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6304(3)
_cell_length_b                   23.6872(4)
_cell_length_c                   16.1100(4)
_cell_measurement_reflns_used    16971
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      71.00
_cell_measurement_theta_min      3.57
_cell_volume                     5546.0(2)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      ' 1576 frames, detector distance = 42 mm'
_diffrn_measurement_device_type  'STADIVARI Pilatus'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_sigmaI/netI    0.1624
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10409
_diffrn_reflns_theta_full        65.99
_diffrn_reflns_theta_max         65.99
_diffrn_reflns_theta_min         3.57
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    3.129
_exptl_absorpt_correction_T_max  0.8262
_exptl_absorpt_correction_T_min  0.4368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          .16
_exptl_crystal_size_mid          .11
_exptl_crystal_size_min          .06
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.829
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     584
_refine_ls_restrained_S_all      0.818
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0711
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0904P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1801
_refine_ls_wR_factor_ref         0.1935
_reflns_number_gt                2553
_reflns_number_total             4820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om6b00767_si_002.cif
_cod_data_source_block           kirill10
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4089146
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.5000 0.15643(4) 0.2500 0.0598(3) Uani 1 2 d SU . .
Ge2 Ge 0.39460(5) 0.20682(3) 0.14485(5) 0.0596(3) Uani 1 1 d U . .
F1 F 0.4626(4) 0.0332(2) 0.1674(4) 0.131(2) Uani 1 1 d U . .
F2 F 0.5584(6) -0.0243(3) 0.0639(5) 0.207(4) Uani 1 1 d U . .
F3 F 0.7065(6) 0.0219(4) 0.0087(5) 0.218(4) Uani 1 1 d U . .
F4 F 0.7651(4) 0.1270(4) 0.0627(4) 0.177(3) Uani 1 1 d U . .
F5 F 0.6774(3) 0.1818(2) 0.1735(3) 0.0931(13) Uani 1 1 d U . .
C1 C 0.2750(2) 0.16910(19) 0.1297(3) 0.0627(15) Uani 1 1 d GU . .
C2 C 0.2667(3) 0.11225(18) 0.1087(3) 0.0795(19) Uani 1 1 d GU . .
H2 H 0.3190 0.0911 0.1022 0.095 Uiso 1 1 calc R . .
C3 C 0.1804(3) 0.08705(17) 0.0976(4) 0.095(2) Uani 1 1 d GU . .
H3 H 0.1748 0.0490 0.0836 0.114 Uiso 1 1 calc R . .
C4 C 0.1024(2) 0.1187(2) 0.1075(4) 0.102(2) Uani 1 1 d GDU A .
C5 C 0.1107(2) 0.1755(2) 0.1284(4) 0.096(2) Uani 1 1 d GU . .
H5 H 0.0585 0.1967 0.1350 0.115 Uiso 1 1 calc R . .
C6 C 0.1970(3) 0.20074(17) 0.1395(3) 0.085(2) Uani 1 1 d GU . .
H6 H 0.2026 0.2388 0.1535 0.103 Uiso 1 1 calc R . .
C7 C 0.3753(3) 0.28587(16) 0.1738(3) 0.0642(15) Uani 1 1 d GU . .
C8 C 0.3801(3) 0.30273(19) 0.2568(2) 0.0803(19) Uani 1 1 d GU . .
H8 H 0.3940 0.2765 0.2994 0.096 Uiso 1 1 calc R . .
C9 C 0.3642(4) 0.3588(2) 0.2762(3) 0.091(2) Uani 1 1 d GU . .
H9 H 0.3675 0.3701 0.3318 0.109 Uiso 1 1 calc R . .
C10 C 0.3435(4) 0.39799(16) 0.2126(4) 0.100(2) Uani 1 1 d GDU B .
C11 C 0.3387(5) 0.3811(2) 0.1296(3) 0.140(4) Uani 1 1 d GU . .
H11 H 0.3249 0.4074 0.0871 0.167 Uiso 1 1 calc R . .
C12 C 0.3546(4) 0.3251(2) 0.1102(2) 0.124(3) Uani 1 1 d GU . .
H12 H 0.3514 0.3138 0.0546 0.149 Uiso 1 1 calc R . .
C13 C 0.4579(3) 0.2043(2) 0.0439(3) 0.0702(16) Uani 1 1 d GU . .
C14 C 0.4404(4) 0.1614(2) -0.0147(3) 0.100(3) Uani 1 1 d GU . .
H14 H 0.3931 0.1358 -0.0099 0.120 Uiso 1 1 calc R . .
C15 C 0.4937(5) 0.1567(3) -0.0805(3) 0.128(3) Uani 1 1 d GU . .
H15 H 0.4820 0.1281 -0.1197 0.154 Uiso 1 1 calc R . .
C16 C 0.5644(4) 0.1950(3) -0.0877(4) 0.134(3) Uani 1 1 d GDU C .
C17 C 0.5819(3) 0.2378(3) -0.0291(4) 0.117(3) Uani 1 1 d GU . .
H17 H 0.6292 0.2634 -0.0339 0.140 Uiso 1 1 calc R . .
C18 C 0.5286(3) 0.2425(2) 0.0367(3) 0.093(2) Uani 1 1 d GU . .
H18 H 0.5403 0.2712 0.0759 0.111 Uiso 1 1 calc R . .
C19 C 0.5697(3) 0.1086(2) 0.1770(3) 0.0762(18) Uani 1 1 d GU . .
C20 C 0.5381(4) 0.0561(2) 0.1478(4) 0.102(2) Uani 1 1 d GU . .
C21 C 0.5841(5) 0.0271(2) 0.0900(4) 0.141(3) Uani 1 1 d GU . .
C22 C 0.6616(5) 0.0508(3) 0.0614(3) 0.147(3) Uani 1 1 d GU . .
C23 C 0.6932(3) 0.1033(3) 0.0906(4) 0.121(3) Uani 1 1 d GU . .
C24 C 0.6472(3) 0.1322(2) 0.1484(3) 0.085(2) Uani 1 1 d GU . .
C25 C 0.0091(8) 0.0943(6) 0.0913(8) 0.165(4) Uani 1 1 d DU . .
F6 F -0.0294(7) 0.1073(7) 0.0134(8) 0.163(3) Uani 0.661(13) 1 d PDU A 1
F7 F -0.0499(7) 0.1140(7) 0.1421(8) 0.163(3) Uani 0.661(13) 1 d PDU A 1
F8 F 0.0041(6) 0.0380(5) 0.0955(10) 0.163(3) Uani 0.661(13) 1 d PDU A 1
F6A F -0.0535(13) 0.1203(11) 0.0419(17) 0.163(3) Uani 0.339(13) 1 d PDU A 2
F7A F -0.0223(14) 0.0817(14) 0.1620(11) 0.163(3) Uani 0.339(13) 1 d PDU A 2
F8A F 0.0170(13) 0.0456(10) 0.0453(17) 0.163(3) Uani 0.339(13) 1 d PDU A 2
C26 C 0.3221(10) 0.4549(4) 0.2340(8) 0.162(4) Uani 1 1 d DU . .
F9 F 0.3106(14) 0.4899(6) 0.1645(10) 0.166(3) Uani 0.464(8) 1 d PDU B 3
F10 F 0.2536(12) 0.4690(6) 0.2719(13) 0.166(3) Uani 0.464(8) 1 d PDU B 3
F11 F 0.3959(11) 0.4816(6) 0.2750(12) 0.166(3) Uani 0.464(8) 1 d PDU B 3
F9A F 0.3510(11) 0.4954(5) 0.1950(11) 0.166(3) Uani 0.536(8) 1 d PDU B 4
F10A F 0.2253(9) 0.4630(5) 0.2152(12) 0.166(3) Uani 0.536(8) 1 d PDU B 4
F11A F 0.3290(13) 0.4647(5) 0.3168(9) 0.166(3) Uani 0.536(8) 1 d PDU B 4
C27 C 0.6291(11) 0.1875(7) -0.1476(9) 0.236(5) Uani 1 1 d DU . .
F12 F 0.6274(11) 0.1478(8) -0.2010(11) 0.232(4) Uani 0.637(10) 1 d PDU C 5
F13 F 0.7167(10) 0.2058(8) -0.1186(9) 0.232(4) Uani 0.637(10) 1 d PDU C 5
F14 F 0.5987(11) 0.2202(8) -0.2159(10) 0.232(4) Uani 0.637(10) 1 d PDU C 5
F12A F 0.6758(17) 0.1370(11) -0.1392(17) 0.232(4) Uani 0.363(10) 1 d PDU C 6
F13A F 0.665(2) 0.2257(11) -0.190(2) 0.232(4) Uani 0.363(10) 1 d PDU C 6
F14A F 0.5740(14) 0.1518(12) -0.2045(15) 0.232(4) Uani 0.363(10) 1 d PDU C 6
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge -1.0885 0.8855 '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
C19 Ge1 C19 110.8(3) . 2_655
C19 Ge1 Ge2 101.06(14) . .
C19 Ge1 Ge2 111.00(14) 2_655 .
C19 Ge1 Ge2 111.00(14) . 2_655
C19 Ge1 Ge2 101.06(14) 2_655 2_655
Ge2 Ge1 Ge2 122.05(6) . 2_655
C1 Ge2 C7 108.4(2) . .
C1 Ge2 C13 112.5(2) . .
C7 Ge2 C13 108.8(2) . .
C1 Ge2 Ge1 110.18(14) . .
C7 Ge2 Ge1 113.31(14) . .
C13 Ge2 Ge1 103.73(14) . .
C2 C1 C6 120.0 . .
C2 C1 Ge2 121.7(3) . .
C6 C1 Ge2 118.3(3) . .
C3 C2 C1 120.0 . .
C2 C3 C4 120.0 . .
C5 C4 C3 120.0 . .
C5 C4 C25 118.3(7) . .
C3 C4 C25 121.6(7) . .
C4 C5 C6 120.0 . .
C5 C6 C1 120.0 . .
C8 C7 C12 120.0 . .
C8 C7 Ge2 120.7(3) . .
C12 C7 Ge2 119.2(3) . .
C7 C8 C9 120.0 . .
C10 C9 C8 120.0 . .
C9 C10 C11 120.0 . .
C9 C10 C26 119.1(6) . .
C11 C10 C26 120.8(6) . .
C12 C11 C10 120.0 . .
C11 C12 C7 120.0 . .
C14 C13 C18 120.0 . .
C14 C13 Ge2 121.2(3) . .
C18 C13 Ge2 118.4(3) . .
C15 C14 C13 120.0 . .
C16 C15 C14 120.0 . .
C15 C16 C17 120.0 . .
C15 C16 C27 122.0(8) . .
C17 C16 C27 117.5(8) . .
C16 C17 C18 120.0 . .
C17 C18 C13 120.0 . .
C20 C19 C24 120.0 . .
C20 C19 Ge1 122.4(3) . .
C24 C19 Ge1 117.3(3) . .
F1 C20 C19 123.3(5) . .
F1 C20 C21 116.6(5) . .
C19 C20 C21 120.0 . .
F2 C21 C22 118.4(7) . .
F2 C21 C20 121.5(7) . .
C22 C21 C20 120.0 . .
F3 C22 C21 119.3(7) . .
F3 C22 C23 120.6(7) . .
C21 C22 C23 120.0 . .
F4 C23 C24 119.0(6) . .
F4 C23 C22 120.9(6) . .
C24 C23 C22 120.0 . .
F5 C24 C23 118.7(4) . .
F5 C24 C19 121.3(4) . .
C23 C24 C19 120.0 . .
F6A C25 F7A 110.4(15) . .
F7 C25 F8 105.9(12) . .
F7 C25 F6 105.0(12) . .
F8 C25 F6 104.7(13) . .
F6A C25 F8A 99.4(17) . .
F7A C25 F8A 109.5(16) . .
F6A C25 C4 119.7(14) . .
F7A C25 C4 110.3(12) . .
F7 C25 C4 113.8(11) . .
F8 C25 C4 115.8(10) . .
F6 C25 C4 110.7(10) . .
F8A C25 C4 106.7(12) . .
F9A C26 F10 111.8(15) . .
F9A C26 F11A 112.1(12) . .
F10 C26 F11 105.8(14) . .
F10 C26 F9 101.6(13) . .
F11 C26 F9 97.5(14) . .
F9A C26 F10A 100.1(13) . .
F11A C26 F10A 98.5(13) . .
F9A C26 C10 120.4(12) . .
F10 C26 C10 124.4(12) . .
F11A C26 C10 113.9(10) . .
F11 C26 C10 111.8(11) . .
F9 C26 C10 112.1(11) . .
F10A C26 C10 108.3(10) . .
F12 C27 F14 84.0(16) . .
F13A C27 F12A 115.8(17) . .
F12 C27 F13 113.9(16) . .
F14 C27 F13 107.2(16) . .
F13A C27 F14A 108(2) . .
F14 C27 F14A 73.3(15) . .
F12A C27 F14A 77.6(17) . .
F12 C27 C16 125.5(13) . .
F13A C27 C16 127.8(15) . .
F14 C27 C16 106.9(13) . .
F12A C27 C16 113.5(14) . .
F13 C27 C16 113.0(11) . .
F14A C27 C16 97.9(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 C19 1.996(4) .
Ge1 C19 1.996(4) 2_655
Ge1 Ge2 2.4641(9) .
Ge1 Ge2 2.4641(9) 2_655
Ge2 C1 1.954(3) .
Ge2 C7 1.958(4) .
Ge2 C13 1.963(4) .
F1 C20 1.301(8) .
F2 C21 1.328(8) .
F3 C22 1.322(7) .
F4 C23 1.317(9) .
F5 C24 1.303(6) .
C1 C2 1.3900 .
C1 C6 1.3900 .
C2 C3 1.3900 .
C3 C4 1.3900 .
C4 C5 1.3900 .
C4 C25 1.476(11) .
C5 C6 1.3900 .
C7 C8 1.3900 .
C7 C12 1.3900 .
C8 C9 1.3900 .
C9 C10 1.3900 .
C10 C11 1.3900 .
C10 C26 1.435(10) .
C11 C12 1.3900 .
C13 C14 1.3900 .
C13 C18 1.3900 .
C14 C15 1.3900 .
C15 C16 1.3900 .
C16 C17 1.3900 .
C16 C27 1.438(12) .
C17 C18 1.3900 .
C19 C20 1.3900 .
C19 C24 1.3900 .
C20 C21 1.3900 .
C21 C22 1.3900 .
C22 C23 1.3900 .
C23 C24 1.3900 .
C25 F6A 1.298(16) .
C25 F7A 1.310(16) .
C25 F7 1.340(13) .
C25 F8 1.339(14) .
C25 F6 1.351(13) .
C25 F8A 1.384(16) .
C26 F9A 1.245(14) .
C26 F10 1.276(14) .
C26 F11A 1.347(14) .
C26 F11 1.356(14) .
C26 F9 1.387(15) .
C26 F10A 1.427(14) .
C27 F12 1.274(15) .
C27 F13A 1.283(16) .
C27 F14 1.376(16) .
C27 F12A 1.377(17) .
C27 F13 1.383(15) .
C27 F14A 1.427(17) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132545222
