#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/84/4318456.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_4318456
loop_
_publ_author_name
'Alan K. Brisdon'
'Ian R. Crossley'
'Robin G. Pritchard'
'John E. Warren'
_publ_section_title
;
 Spectroscopic and Structural Assignment of the Absolute Stereochemistry
 in a Series of 1,2-Difluorovinyl Organometalloids. The First
 Crystallographic Characterization and Structural Series of Group 14
 Fluorovinyl Compounds
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4748
_journal_page_last               4755
_journal_paper_doi               10.1021/ic025593o
_journal_volume                  41
_journal_year                    2002
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H16 F2 Ge1'
_chemical_formula_structural     'C20 H16 F2 Ge1'
_chemical_formula_sum            'C20 H16 F2 Ge'
_chemical_formula_weight         366.92
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2001-07-27T15:21:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 129.109(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2386(6)
_cell_length_b                   29.170(3)
_cell_length_c                   7.3196(6)
_cell_measurement_reflns_used    1013
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      1.018
_cell_measurement_wavelength     0.71073
_cell_volume                     1696.3(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.916
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.135874E-1
_diffrn_orient_matrix_UB_12      -0.7391E-2
_diffrn_orient_matrix_UB_13      -0.1206
_diffrn_orient_matrix_UB_21      -0.969878E-1
_diffrn_orient_matrix_UB_22      -0.217687E-1
_diffrn_orient_matrix_UB_23      -0.780146E-1
_diffrn_orient_matrix_UB_31      -0.790728E-1
_diffrn_orient_matrix_UB_32      0.254307E-1
_diffrn_orient_matrix_UB_33      -0.101831
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2206
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.88
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    1.821
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.44(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2206
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0508P)²+3.4034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                1983
_reflns_number_total             2206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic025593o_s1_4.cif
_cod_data_source_block           ph3gecfcfh
_cod_original_cell_volume        1696.3(2)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4318456
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'
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
C1 C 0.8189(11) 0.1840(3) 0.6189(15) 0.039(2) Uani 1 1 d . . .
C2 C 0.9684(12) 0.1840(3) 0.6875(18) 0.067(3) Uani 1 1 d . . .
C3 C 0.8560(10) 0.1059(3) 0.9459(13) 0.0299(19) Uani 1 1 d . . .
C4 C 0.9731(9) 0.1300(3) 1.1586(12) 0.0441(18) Uani 1 1 d . . .
H4 H 0.9748 0.1626 1.1584 0.053 Uiso 1 1 calc R . .
C5 C 1.0855(10) 0.1062(3) 1.3672(13) 0.053(2) Uani 1 1 d . . .
H5 H 1.1641 0.1226 1.5095 0.064 Uiso 1 1 calc R . .
C6 C 1.0838(12) 0.0593(3) 1.3692(16) 0.059(2) Uani 1 1 d . . .
H6 H 1.1596 0.0432 1.5132 0.07 Uiso 1 1 calc R . .
C7 C 0.9730(12) 0.0357(3) 1.1642(15) 0.060(2) Uani 1 1 d . . .
H7 H 0.9732 0.0031 1.1655 0.072 Uiso 1 1 calc R . .
C8 C 0.8598(10) 0.0593(3) 0.9535(12) 0.0443(18) Uani 1 1 d . . .
H8 H 0.7837 0.0424 0.812 0.053 Uiso 1 1 calc R . .
C9 C 0.5342(10) 0.1719(3) 0.6624(13) 0.0315(18) Uani 1 1 d . . .
C10 C 0.5410(8) 0.1698(2) 0.8579(12) 0.0362(15) Uani 1 1 d . . .
H10 H 0.6219 0.1507 0.9872 0.043 Uiso 1 1 calc R . .
C11 C 0.4298(9) 0.1955(3) 0.8652(12) 0.0450(18) Uani 1 1 d . . .
H11 H 0.4335 0.1935 0.9979 0.054 Uiso 1 1 calc R . .
C12 C 0.3143(10) 0.2240(3) 0.6797(13) 0.0439(18) Uani 1 1 d . . .
H12 H 0.2411 0.2423 0.6872 0.053 Uiso 1 1 calc R . .
C13 C 0.3052(9) 0.2258(3) 0.4847(12) 0.0431(17) Uani 1 1 d . . .
H13 H 0.2232 0.2448 0.3556 0.052 Uiso 1 1 calc R . .
C14 C 0.4155(8) 0.2000(2) 0.4743(11) 0.0351(16) Uani 1 1 d . . .
H14 H 0.4095 0.2017 0.3395 0.042 Uiso 1 1 calc R . .
C15 C 0.5820(10) 0.0966(3) 0.3889(14) 0.033(2) Uani 1 1 d . . .
C16 C 0.4113(9) 0.0871(3) 0.2666(11) 0.0425(18) Uani 1 1 d . . .
H16 H 0.3518 0.1022 0.3091 0.051 Uiso 1 1 calc R . .
C17 C 0.3279(12) 0.0553(3) 0.0806(16) 0.059(2) Uani 1 1 d . . .
H17 H 0.213 0.0479 -0.0005 0.071 Uiso 1 1 calc R . .
C18 C 0.4160(12) 0.0352(3) 0.0194(13) 0.058(2) Uani 1 1 d . . .
H18 H 0.3604 0.0138 -0.1069 0.069 Uiso 1 1 calc R . .
C19 C 0.5820(13) 0.0449(3) 0.1343(14) 0.059(2) Uani 1 1 d . . .
H19 H 0.6398 0.0302 0.0881 0.071 Uiso 1 1 calc R . .
C20 C 0.6665(11) 0.0764(2) 0.3190(13) 0.0441(18) Uani 1 1 d . . .
H20 H 0.7807 0.0839 0.396 0.053 Uiso 1 1 calc R . .
F1 F 0.7272(6) 0.22319(18) 0.4970(9) 0.0670(13) Uani 1 1 d . . .
F2 F 1.0715(9) 0.1481(3) 0.8066(15) 0.113(3) Uani 1 1 d . . .
Ge1 Ge 0.69724(7) 0.138666(18) 0.65797(8) 0.03029(19) Uani 1 1 d . . .
H2 H 1.055(10) 0.211(3) 0.696(13) 0.04(2) Uiso 1 1 d . . .
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 0 '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
_geom_angle_publ_flag
C2 C1 F1 114.3(8) . . ?
C2 C1 Ge1 131.2(7) . . ?
F1 C1 Ge1 114.5(6) . . ?
C1 C2 F2 120.8(9) . . ?
C8 C3 C4 118.0(8) . . ?
C8 C3 Ge1 121.7(6) . . ?
C4 C3 Ge1 120.3(6) . . ?
C5 C4 C3 120.1(8) . . ?
C6 C5 C4 120.3(8) . . ?
C7 C6 C5 120.0(8) . . ?
C6 C7 C8 120.1(9) . . ?
C3 C8 C7 121.4(8) . . ?
C10 C9 C14 119.3(7) . . ?
C10 C9 Ge1 120.6(6) . . ?
C14 C9 Ge1 120.0(5) . . ?
C9 C10 C11 120.3(7) . . ?
C12 C11 C10 120.1(7) . . ?
C13 C12 C11 120.0(7) . . ?
C12 C13 C14 120.6(7) . . ?
C9 C14 C13 119.6(6) . . ?
C20 C15 C16 119.9(8) . . ?
C20 C15 Ge1 121.2(6) . . ?
C16 C15 Ge1 118.9(6) . . ?
C15 C16 C17 120.0(8) . . ?
C18 C17 C16 118.5(9) . . ?
C17 C18 C19 122.0(8) . . ?
C18 C19 C20 120.2(8) . . ?
C15 C20 C19 119.2(8) . . ?
C3 Ge1 C9 111.8(3) . . ?
C3 Ge1 C1 108.7(4) . . ?
C9 Ge1 C1 107.3(3) . . ?
C3 Ge1 C15 110.3(3) . . ?
C9 Ge1 C15 110.4(3) . . ?
C1 Ge1 C15 108.1(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.275(13) . ?
C1 F1 1.388(9) . ?
C1 Ge1 1.958(9) . ?
C2 F2 1.345(11) . ?
C3 C8 1.361(11) . ?
C3 C4 1.415(11) . ?
C3 Ge1 1.917(8) . ?
C4 C5 1.385(11) . ?
C5 C6 1.367(13) . ?
C6 C7 1.366(13) . ?
C7 C8 1.393(11) . ?
C9 C10 1.389(10) . ?
C9 C14 1.392(11) . ?
C9 Ge1 1.947(8) . ?
C10 C11 1.392(10) . ?
C11 C12 1.380(11) . ?
C12 C13 1.372(10) . ?
C13 C14 1.399(9) . ?
C15 C20 1.384(11) . ?
C15 C16 1.399(11) . ?
C15 Ge1 1.961(8) . ?
C16 C17 1.407(11) . ?
C17 C18 1.367(13) . ?
C18 C19 1.368(13) . ?
C19 C20 1.393(12) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661068
