#------------------------------------------------------------------------------
#$Date: 2024-07-05 16:11:35 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292762 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/31/7133126.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_7133126
loop_
_publ_author_name
'Lu, Xiao-Yu'
'Qian, Yu-Jun'
'Sun, Hai-Lun'
'Su, Meng-Xue'
'Wang, Zi-Zhen'
'Jiang, Fan'
'Zhou, Xin-Yue'
'Sun, Yan-Xi'
'Shi, Wan-Li'
'Wan, Ji-Ru'
_publ_section_title
;
 Photoinduced decarboxylative germylation of α-fluoroacrylic acids:
 access to germylated monofluoroalkenes.
;
_journal_issue                   51
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6556
_journal_page_last               6559
_journal_paper_doi               10.1039/d4cc02037e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C27 H23 F Ge O'
_chemical_formula_sum            'C27 H23 F Ge O'
_chemical_formula_weight         455.04
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-22
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-22 deposited with the CCDC.	2024-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                106.2010(10)
_cell_angle_beta                 104.2420(10)
_cell_angle_gamma                105.0350(10)
_cell_formula_units_Z            2
_cell_length_a                   9.87890(10)
_cell_length_b                   11.0575(2)
_cell_length_c                   11.8202(2)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.948
_cell_measurement_theta_min      3.872
_cell_volume                     1124.69(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17576
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.949
_diffrn_reflns_theta_min         3.870
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.337
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1651 before and 0.0786 after correction.
The Ratio of minimum to maximum transmission is 0.7668.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4228
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0461P)²+0.7452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4030
_reflns_number_total             4228
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02037e2.cif
_cod_data_source_block           240522lxy
_cod_depositor_comments          'Adding full bibliography for 7133126.cif.'
_cod_database_code               7133126
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.805
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 Ge1, C1
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C25(H25), C26(H26), C27(H27)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.70785(2) 0.24626(2) 0.38279(2) 0.01985(10) Uani 1 1 d . U . . .
F1 F 0.55768(13) 0.38569(13) 0.51092(11) 0.0373(3) Uani 1 1 d . . . . .
O1 O 0.87089(18) 0.81779(17) 1.10276(14) 0.0433(4) Uani 1 1 d . . . . .
C1 C 0.6966(2) 0.37463(19) 0.52872(18) 0.0231(4) Uani 1 1 d . U . . .
C2 C 0.8028(2) 0.44083(19) 0.63999(18) 0.0233(4) Uani 1 1 d . . . . .
H2 H 0.894244 0.426178 0.644112 0.028 Uiso 1 1 calc R U . . .
C3 C 0.8060(2) 0.53241(18) 0.75798(17) 0.0226(4) Uani 1 1 d . . . . .
C4 C 0.6905(2) 0.5787(2) 0.77426(18) 0.0254(4) Uani 1 1 d . . . . .
H4 H 0.598676 0.545132 0.706589 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7078(2) 0.6732(2) 0.88798(19) 0.0282(4) Uani 1 1 d . . . . .
H5 H 0.628316 0.703806 0.897358 0.034 Uiso 1 1 calc R U . . .
C6 C 0.8409(2) 0.7227(2) 0.98742(19) 0.0303(4) Uani 1 1 d . . . . .
C7 C 0.9548(2) 0.6744(2) 0.9742(2) 0.0385(5) Uani 1 1 d . . . . .
H7 H 1.045011 0.705801 1.043100 0.046 Uiso 1 1 calc R U . . .
C8 C 0.9375(2) 0.5812(2) 0.8617(2) 0.0326(5) Uani 1 1 d . . . . .
H8 H 1.016499 0.549179 0.854093 0.039 Uiso 1 1 calc R U . . .
C9 C 0.7710(4) 0.8881(3) 1.1136(3) 0.0594(8) Uani 1 1 d . . . . .
H9A H 0.757069 0.925635 1.047405 0.089 Uiso 1 1 calc R U . . .
H9B H 0.812077 0.961287 1.195790 0.089 Uiso 1 1 calc R U . . .
H9C H 0.674709 0.826220 1.105038 0.089 Uiso 1 1 calc R U . . .
C10 C 0.9006(2) 0.22440(18) 0.43028(17) 0.0217(4) Uani 1 1 d . . . . .
C11 C 0.9496(2) 0.1863(2) 0.53160(19) 0.0284(4) Uani 1 1 d . . . . .
H11 H 0.887271 0.169500 0.579319 0.034 Uiso 1 1 calc R U . . .
C12 C 1.0883(2) 0.1726(2) 0.5636(2) 0.0345(5) Uani 1 1 d . . . . .
H12 H 1.120090 0.146297 0.632625 0.041 Uiso 1 1 calc R U . . .
C13 C 1.1803(2) 0.1973(2) 0.4950(2) 0.0385(5) Uani 1 1 d . . . . .
H13 H 1.275438 0.188336 0.516927 0.046 Uiso 1 1 calc R U . . .
C14 C 1.1333(3) 0.2348(3) 0.3948(3) 0.0407(6) Uani 1 1 d . . . . .
H14 H 1.196201 0.251023 0.347385 0.049 Uiso 1 1 calc R U . . .
C15 C 0.9952(2) 0.2491(2) 0.3624(2) 0.0307(4) Uani 1 1 d . . . . .
H15 H 0.964672 0.275839 0.293486 0.037 Uiso 1 1 calc R U . . .
C16 C 0.6861(2) 0.31183(19) 0.24474(17) 0.0230(4) Uani 1 1 d . . . . .
C17 C 0.7175(2) 0.4474(2) 0.2637(2) 0.0308(4) Uani 1 1 d . . . . .
H17 H 0.747298 0.511291 0.346122 0.037 Uiso 1 1 calc R U . . .
C18 C 0.7058(3) 0.4902(2) 0.1631(2) 0.0396(5) Uani 1 1 d . . . . .
H18 H 0.725615 0.582908 0.176653 0.048 Uiso 1 1 calc R U . . .
C19 C 0.6649(3) 0.3976(3) 0.0424(2) 0.0411(6) Uani 1 1 d . . . . .
H19 H 0.657714 0.427122 -0.026334 0.049 Uiso 1 1 calc R U . . .
C20 C 0.6352(3) 0.2640(3) 0.0226(2) 0.0372(5) Uani 1 1 d . . . . .
H20 H 0.608048 0.200999 -0.059859 0.045 Uiso 1 1 calc R U . . .
C21 C 0.6445(2) 0.2199(2) 0.12243(19) 0.0303(4) Uani 1 1 d . . . . .
H21 H 0.622458 0.126777 0.107685 0.036 Uiso 1 1 calc R U . . .
C22 C 0.5433(2) 0.07808(19) 0.33328(17) 0.0228(4) Uani 1 1 d . . . . .
C23 C 0.5669(2) -0.0345(2) 0.35245(19) 0.0276(4) Uani 1 1 d . . . . .
H23 H 0.665925 -0.031461 0.386488 0.033 Uiso 1 1 calc R U . . .
C24 C 0.4475(2) -0.1512(2) 0.32249(19) 0.0324(5) Uani 1 1 d . . . . .
H24 H 0.465046 -0.227413 0.336018 0.039 Uiso 1 1 calc R U . . .
C25 C 0.3030(2) -0.1561(2) 0.27293(18) 0.0304(5) Uani 1 1 d . . . . .
H25 H 0.221357 -0.235885 0.252311 0.036 Uiso 1 1 calc R U . . .
C26 C 0.2771(2) -0.0456(2) 0.2533(2) 0.0339(5) Uani 1 1 d . . . . .
H26 H 0.177795 -0.049007 0.219767 0.041 Uiso 1 1 calc R U . . .
C27 C 0.3971(2) 0.0711(2) 0.2829(2) 0.0305(4) Uani 1 1 d . . . . .
H27 H 0.378922 0.146661 0.268444 0.037 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge -1.5187 0.6907 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
C10 Ge1 C1 108.30(8) . . ?
C10 Ge1 C16 110.05(8) . . ?
C10 Ge1 C22 111.78(8) . . ?
C16 Ge1 C1 110.25(8) . . ?
C22 Ge1 C1 107.16(8) . . ?
C22 Ge1 C16 109.26(8) . . ?
C6 O1 C9 117.49(18) . . ?
F1 C1 Ge1 113.48(12) . . ?
C2 C1 Ge1 126.66(15) . . ?
C2 C1 F1 119.67(17) . . ?
C1 C2 H2 113.9 . . ?
C1 C2 C3 132.11(18) . . ?
C3 C2 H2 113.9 . . ?
C4 C3 C2 125.27(17) . . ?
C4 C3 C8 117.46(18) . . ?
C8 C3 C2 117.23(17) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.10(18) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.98(19) . . ?
C6 C5 H5 120.0 . . ?
O1 C6 C5 124.77(19) . . ?
O1 C6 C7 115.58(19) . . ?
C5 C6 C7 119.65(19) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 H8 119.2 . . ?
C7 C8 C3 121.52(19) . . ?
C7 C8 H8 119.2 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 Ge1 122.37(14) . . ?
C11 C10 C15 118.16(18) . . ?
C15 C10 Ge1 119.47(15) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.92(19) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.7(2) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C17 C16 Ge1 122.45(15) . . ?
C17 C16 C21 118.61(19) . . ?
C21 C16 Ge1 118.86(15) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.4(2) . . ?
C20 C21 H21 119.8 . . ?
C23 C22 Ge1 121.80(15) . . ?
C23 C22 C27 118.47(18) . . ?
C27 C22 Ge1 119.66(15) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 120.92(19) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.8(2) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.26(19) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.8(2) . . ?
C27 C26 H26 120.1 . . ?
C22 C27 C26 120.8(2) . . ?
C22 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
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
Ge1 C1 1.9525(19) . ?
Ge1 C10 1.9461(19) . ?
Ge1 C16 1.9502(19) . ?
Ge1 C22 1.9493(19) . ?
F1 C1 1.379(2) . ?
O1 C6 1.376(2) . ?
O1 C9 1.414(3) . ?
C1 C2 1.324(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.465(3) . ?
C3 C4 1.400(3) . ?
C3 C8 1.402(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 C7 1.388(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.375(3) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.396(3) . ?
C10 C15 1.396(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.375(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(3) . ?
C16 C21 1.401(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.369(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.391(3) . ?
C22 C27 1.393(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.390(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.383(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.380(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.393(3) . ?
C27 H27 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ge1 C1 C2 C3 -175.77(16) . . . . ?
Ge1 C10 C11 C12 -179.50(16) . . . . ?
Ge1 C10 C15 C14 179.70(17) . . . . ?
Ge1 C16 C17 C18 177.62(16) . . . . ?
Ge1 C16 C21 C20 -176.77(16) . . . . ?
Ge1 C22 C23 C24 176.61(15) . . . . ?
Ge1 C22 C27 C26 -176.36(16) . . . . ?
F1 C1 C2 C3 -1.0(3) . . . . ?
O1 C6 C7 C8 -178.5(2) . . . . ?
C1 C2 C3 C4 -5.3(4) . . . . ?
C1 C2 C3 C8 177.1(2) . . . . ?
C2 C3 C4 C5 -175.41(19) . . . . ?
C2 C3 C8 C7 175.7(2) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C3 C8 C7 -2.1(3) . . . . ?
C4 C5 C6 O1 178.7(2) . . . . ?
C4 C5 C6 C7 -2.0(3) . . . . ?
C5 C6 C7 C8 2.1(4) . . . . ?
C6 C7 C8 C3 0.0(4) . . . . ?
C8 C3 C4 C5 2.2(3) . . . . ?
C9 O1 C6 C5 -12.4(4) . . . . ?
C9 O1 C6 C7 168.3(2) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C10 C15 C14 0.5(3) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C10 -0.6(4) . . . . ?
C15 C10 C11 C12 -0.3(3) . . . . ?
C16 C17 C18 C19 -1.2(3) . . . . ?
C17 C16 C21 C20 0.1(3) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
C19 C20 C21 C16 -0.8(3) . . . . ?
C21 C16 C17 C18 0.9(3) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C22 C27 C26 0.6(3) . . . . ?
C23 C24 C25 C26 -0.1(3) . . . . ?
C24 C25 C26 C27 0.4(3) . . . . ?
C25 C26 C27 C22 -0.6(3) . . . . ?
C27 C22 C23 C24 -0.2(3) . . . . ?
