Visible Light-Induced Photoredox Construction of Trifluoromethylated Quaternary Carbon Centers from Trifluoromethylated Tertiary Bromides.
Huan, Feng; Chen, Qing-Yun; Guo, Yong; The Journal of organic chemistry 81 (2016) 7051–7063; doi:10.1021/acs.joc.6b00930

data_4036920
_publ_section_title
;
 Visible Light-Induced Photoredox Construction of Trifluoromethylated
 Quaternary Carbon Centers from Trifluoromethylated Tertiary Bromides.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7051
_journal_page_last               7063
_journal_paper_doi               10.1021/acs.joc.6b00930
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C15 H14 Br F4 N O3'
_chemical_formula_sum            'C15 H14 Br F4 N O3'
_chemical_formula_weight         412.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.319(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9041(16)
_cell_length_b                   10.6234(16)
_cell_length_c                   14.133(2)
_cell_measurement_reflns_used    2561
_cell_measurement_temperature    293
_cell_measurement_theta_max      23.94
_cell_measurement_theta_min      2.35
_cell_volume                     1637.1(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13215
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.710
_diffrn_reflns_theta_min         2.353
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.567
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1373 before and 0.0361 after correction.
The Ratio of minimum to maximum transmission is 0.6599.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.0435P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1149
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2119
_reflns_number_total             3822
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00930_si_001.cif
_cod_data_source_block           mo_dm15895_0m
_cod_database_code               4036920
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.748
_shelx_estimated_absorpt_t_min   0.628
_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.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              10732
_shelx_hkl_checksum              80731
_olex2_submission_special_instructions 'No special instructions were received'