#------------------------------------------------------------------------------
#$Date: 2022-04-03 22:19:43 +0300 (Sun, 03 Apr 2022) $
#$Revision: 274235 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519379.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_4519379
loop_
_publ_author_name
'Louis-Goff, Thomas'
'Trinh, Huu Vinh'
'Chen, Eileen'
'Rheingold, Arnold L.'
'Ehm, Christian'
'Hyvl, Jakub'
_publ_section_title
;
 Stabilizing Effect of Pre-equilibria: A Trifluoromethyl Complex as a CF2
 Reservoir in Catalytic Olefin Difluorocarbenation
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              3719
_journal_page_last               3730
_journal_paper_doi               10.1021/acscatal.1c05959
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C15 H14 Bi F3'
_chemical_formula_sum            'C15 H14 Bi F3'
_chemical_formula_weight         460.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-05-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.435(3)
_cell_length_b                   9.004(2)
_cell_length_c                   18.230(4)
_cell_measurement_reflns_used    7532
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      3.23
_cell_volume                     2861.8(10)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21282
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.149
_diffrn_reflns_theta_min         2.336
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    12.338
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.2661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1497 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.3569.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.136
_exptl_crystal_description       plate
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.692
_refine_diff_density_min         -1.986
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0248
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0223P)²+3.8898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0568
_refine_ls_wR_factor_ref         0.0612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2534
_reflns_number_total             3159
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c05959_si_005.cif
_cod_data_source_block           hyvl100_0m_a
_cod_original_cell_volume        2861.8(11)
_cod_database_code               4519379
_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   0.372
_shelx_estimated_absorpt_t_min   0.124
_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.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
Bi1 Bi 0.35527(2) 0.83543(2) 0.74564(2) 0.01738(7) Uani 1 1 d . . . . .
F1 F 0.31756(15) 0.5130(3) 0.80678(13) 0.0310(6) Uani 1 1 d . . . . .
F2 F 0.27956(15) 0.6852(3) 0.87975(13) 0.0334(6) Uani 1 1 d . . . . .
F3 F 0.39908(14) 0.6283(3) 0.87378(14) 0.0318(6) Uani 1 1 d . . . . .
C1 C 0.3361(2) 0.6493(5) 0.8318(2) 0.0198(9) Uani 1 1 d . . . . .
C2 C 0.4470(2) 0.7094(4) 0.6872(2) 0.0175(8) Uani 1 1 d . . . . .
C3 C 0.4367(2) 0.5657(5) 0.6601(2) 0.0213(9) Uani 1 1 d . . . . .
H3 H 0.390615 0.513554 0.670384 0.026 Uiso 1 1 calc R U . . .
C4 C 0.4939(2) 0.4981(5) 0.6179(2) 0.0211(8) Uani 1 1 d . . . . .
H4 H 0.486401 0.399578 0.600688 0.025 Uiso 1 1 calc R U . . .
C5 C 0.5612(2) 0.5716(5) 0.60078(19) 0.0189(8) Uani 1 1 d . . . . .
C6 C 0.5717(2) 0.7148(5) 0.62900(19) 0.0190(8) Uani 1 1 d . . . . .
H6 H 0.617996 0.766641 0.618890 0.023 Uiso 1 1 calc R U . . .
C7 C 0.5158(2) 0.7818(5) 0.6714(2) 0.0182(8) Uani 1 1 d . . . . .
H7 H 0.524320 0.878896 0.690131 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6218(2) 0.5005(5) 0.5531(2) 0.0262(9) Uani 1 1 d . . . . .
H8A H 0.633420 0.566039 0.511650 0.039 Uiso 1 1 calc R U . . .
H8B H 0.602784 0.405089 0.534649 0.039 Uiso 1 1 calc R U . . .
H8C H 0.668380 0.484172 0.582031 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2614(2) 0.7475(4) 0.67406(19) 0.0164(8) Uani 1 1 d . . . . .
C10 C 0.2734(2) 0.7133(5) 0.6004(2) 0.0246(9) Uani 1 1 d . . . . .
H10 H 0.322607 0.728090 0.579269 0.029 Uiso 1 1 calc R U . . .
C11 C 0.2140(2) 0.6576(5) 0.5577(2) 0.0253(10) Uani 1 1 d . . . . .
H11 H 0.223344 0.632911 0.507843 0.030 Uiso 1 1 calc R U . . .
C12 C 0.1411(2) 0.6374(5) 0.5867(2) 0.0200(9) Uani 1 1 d . . . . .
C13 C 0.1290(2) 0.6752(4) 0.6596(2) 0.0175(8) Uani 1 1 d . . . . .
H13 H 0.079329 0.663812 0.680378 0.021 Uiso 1 1 calc R U . . .
C14 C 0.1886(2) 0.7296(4) 0.7026(2) 0.0163(8) Uani 1 1 d . . . . .
H14 H 0.179106 0.754757 0.752359 0.020 Uiso 1 1 calc R U . . .
C15 C 0.0772(2) 0.5752(5) 0.5406(2) 0.0260(10) Uani 1 1 d . . . . .
H15A H 0.048878 0.500765 0.568946 0.039 Uiso 1 1 calc R U . . .
H15B H 0.098727 0.528850 0.496552 0.039 Uiso 1 1 calc R U . . .
H15C H 0.042383 0.655596 0.526282 0.039 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 0.0033 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'
Bi Bi -4.1077 10.2566 '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'
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 Bi1 C1 93.40(14) . . ?
C2 Bi1 C9 93.78(14) . . ?
C9 Bi1 C1 91.94(14) . . ?
F1 C1 Bi1 117.6(2) . . ?
F1 C1 F2 105.1(3) . . ?
F1 C1 F3 105.0(3) . . ?
F2 C1 Bi1 111.7(3) . . ?
F3 C1 Bi1 111.5(3) . . ?
F3 C1 F2 105.0(3) . . ?
C3 C2 Bi1 123.2(3) . . ?
C7 C2 Bi1 118.5(3) . . ?
C7 C2 C3 118.1(4) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.4(4) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 118.0(4) . . ?
C4 C5 C8 121.3(4) . . ?
C6 C5 C8 120.7(4) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.0(4) . . ?
C7 C6 H6 119.5 . . ?
C2 C7 H7 119.4 . . ?
C6 C7 C2 121.1(4) . . ?
C6 C7 H7 119.4 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 Bi1 122.0(3) . . ?
C14 C9 Bi1 119.6(3) . . ?
C14 C9 C10 118.4(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.5(4) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.1(4) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C13 118.2(4) . . ?
C11 C12 C15 120.9(4) . . ?
C13 C12 C15 120.9(4) . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 C13 121.1(3) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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
Bi1 C1 2.321(4) . ?
Bi1 C2 2.232(4) . ?
Bi1 C9 2.238(4) . ?
F1 C1 1.348(5) . ?
F2 C1 1.356(5) . ?
F3 C1 1.352(4) . ?
C2 C3 1.396(6) . ?
C2 C7 1.395(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(6) . ?
C5 C6 1.400(6) . ?
C5 C8 1.510(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(6) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.393(5) . ?
C9 C14 1.381(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(6) . ?
C12 C13 1.387(5) . ?
C12 C15 1.504(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(5) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
Bi1 C2 C3 C4 173.9(3) . . . . ?
Bi1 C2 C7 C6 -173.5(3) . . . . ?
Bi1 C9 C10 C11 179.4(3) . . . . ?
Bi1 C9 C14 C13 -180.0(3) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C3 C2 C7 C6 1.2(5) . . . . ?
C3 C4 C5 C6 2.1(5) . . . . ?
C3 C4 C5 C8 -177.9(4) . . . . ?
C4 C5 C6 C7 -1.4(5) . . . . ?
C5 C6 C7 C2 -0.3(6) . . . . ?
C7 C2 C3 C4 -0.5(5) . . . . ?
C8 C5 C6 C7 178.6(3) . . . . ?
C9 C10 C11 C12 1.2(7) . . . . ?
C10 C9 C14 C13 1.6(6) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C10 C11 C12 C15 -179.2(4) . . . . ?
C11 C12 C13 C14 -1.0(6) . . . . ?
C12 C13 C14 C9 0.0(6) . . . . ?
C14 C9 C10 C11 -2.2(6) . . . . ?
C15 C12 C13 C14 178.6(4) . . . . ?
