Visible-Light-Promoted C(sp<sup>3</sup>)-C(sp<sup>2</sup>) Cross-Dehydrogenative Coupling of Tertiary Amine with Imidazopyridine.
Kibriya, Golam; Bagdi, Avik Kumar; Hajra, Alakananda; The Journal of organic chemistry 83 (2018) 10619–10626; doi:10.1021/acs.joc.8b01433

data_4035086
_publ_section_title
;
 Visible-Light-Promoted C(sp<sup>3</sup>)-C(sp<sup>2</sup>)
 Cross-Dehydrogenative Coupling of Tertiary Amine with Imidazopyridine.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10619
_journal_page_last               10626
_journal_paper_doi               10.1021/acs.joc.8b01433
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C28 H22 F N3, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C28.5 H23 Cl F N3'
_chemical_formula_weight         461.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 116.115(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.7615(15)
_cell_length_b                   19.7057(19)
_cell_length_c                   16.691(2)
_cell_measurement_reflns_used    184
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.764
_cell_measurement_theta_min      1.421
_cell_volume                     4654.9(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1190
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            76921
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.738
_diffrn_reflns_theta_min         1.772
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2168
_exptl_crystal_size_max          0.36000
_exptl_crystal_size_mid          0.28000
_exptl_crystal_size_min          0.25000
_refine_diff_density_max         0.928
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.134
_refine_ls_abs_structure_details
;
 Flack x determined using 3083 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(11)
_refine_ls_extinction_coef       0.0164(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     605
_refine_ls_number_reflns         11925
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0873
_refine_ls_shift/su_max          0.083
_refine_ls_shift/su_mean         0.081
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1099P)^2^+8.7881P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2016
_refine_ls_wR_factor_ref         0.2616
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                7867
_reflns_number_total             11925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01433_si_002.cif
_cod_data_source_block           vbchem298_b
_cod_depositor_comments
;

2020-07-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'C c'
_cod_original_formula_moiety     '2(C28 H22 F N3), C H2 Cl2'
_cod_original_formula_sum        'C57 H46 Cl2 F2 N6'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     923.94
_cod_database_code               4035086
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.031
_shelx_estimated_absorpt_t_max   0.046
_exptl_absorpt_special_details   SADABS
_shelx_res_checksum              59530
_shelx_hkl_checksum              11356