Stabilizing Effect of Pre-equilibria: A Trifluoromethyl Complex as a CF2 Reservoir in Catalytic Olefin Difluorocarbenation
Louis-Goff, Thomas; Trinh, Huu Vinh; Chen, Eileen; Rheingold, Arnold L.; Ehm, Christian; Hyvl, Jakub; ACS Catalysis 12 (2022) 3719–3730; doi:10.1021/acscatal.1c05959

data_4519378
_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         'C19 H21 Bi F3 N'
_chemical_formula_sum            'C19 H21 Bi F3 N'
_chemical_formula_weight         529.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.483(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9594(6)
_cell_length_b                   9.2852(5)
_cell_length_c                   14.7567(9)
_cell_measurement_reflns_used    2984
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.896
_cell_measurement_theta_min      2.592
_cell_volume                     1775.09(17)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13129
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_min         2.699
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.961
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0991 before and 0.0420 after correction. The Ratio of minimum to maximum transmission is 0.6005. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.048
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     219
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0291
_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/[\s^2^(Fo^2^)+(0.0112P)^2^+3.2330P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0519
_refine_ls_wR_factor_ref         0.0554
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3581
_reflns_number_total             4390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c05959_si_004.cif
_cod_data_source_block           hyvl03_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4519378
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.154
_shelx_estimated_absorpt_t_min   0.133
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C6)
Uanis(C19) = Uanis(C14)
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
4.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C2(H2), C5(H5), C3(H3), C4(H4), C12(H12), C11(H11), C10(H10)
4.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              69673
_shelx_hkl_checksum              21956
_olex2_submission_special_instructions 'No special instructions were received'