Difluorination of α-(Bromomethyl)styrenes via I(I)/I(III) Catalysis: Facile Access to Electrophilic Linchpins for Drug Discovery
Häfliger, Joel; Livingstone, Keith; Daniliuc, Constantin; Gilmour, Ryan; Chemical Science  (2021) –; doi:10.1039/D1SC01132D

data_1561311
_publ_section_title
;
 Difluorination of \a-(Bromomethyl)styrenes via I(I)/I(III) Catalysis:
 Facile Access to Electrophilic Linchpins for Drug Discovery
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01132D
_journal_year                    2021
_chemical_formula_sum            'C17 H12 Br F2 N O2'
_chemical_formula_weight         380.19
_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
_audit_creation_method           'APEX3 v2019.11-0'
_audit_update_record
;
2021-01-13 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                67.712(5)
_cell_angle_beta                 85.665(5)
_cell_angle_gamma                88.114(6)
_cell_formula_units_Z            2
_cell_length_a                   4.7731(8)
_cell_length_b                   11.3543(17)
_cell_length_c                   14.650(2)
_cell_measurement_reflns_used    6241
_cell_measurement_temperature    102.(2)
_cell_measurement_theta_max      26.8468
_cell_measurement_theta_min      2.8698
_cell_volume                     732.53(19)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker APEX3 v2019.11-0 Photon III'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      102.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'Bruker D8 Venture Photon III Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi/omega scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_limit_h_max       5
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_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14235
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.87
_diffrn_source                   MoK\a
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'micro focus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.837
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption
correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M.
& Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.485
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+0.5703P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2325
_reflns_number_total             2620
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01132d2.cif
_cod_data_source_block           gil9967
_cod_original_cell_volume        732.5(2)
_cod_database_code               1561311
_shelx_res_checksum              74722
_shelx_hkl_checksum              29664