Iron-Catalyzed 1,2-Selective Hydroboration of N-Heteroarenes.
Zhang, Fanjun; Song, Heng; Zhuang, Xuewen; Tung, Chen-Ho; Wang, Wenguang; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b11416

data_4126794
_publ_section_title
;
 Iron-Catalyzed 1,2-Selective Hydroboration of N-Heteroarenes.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b11416
_journal_year                    2017
_chemical_formula_sum            'C33 H34 Fe N P S'
_chemical_formula_weight         563.49
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 103.953(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.063(6)
_cell_length_b                   9.464(3)
_cell_length_c                   16.113(5)
_cell_measurement_reflns_used    5925
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.501
_cell_measurement_theta_min      2.202
_cell_volume                     2821.2(15)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8041
_diffrn_reflns_point_group_measured_fraction_full 0.817
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.199
_exptl_absorpt_coefficient_mu    0.688
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1609 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.126(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4179
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0330P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0585
_refine_ls_wR_factor_ref         0.0592
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.660
_reflns_Friedel_fraction_max     0.677
_reflns_number_gt                4072
_reflns_number_total             4179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b11416_si_002.cif
_cod_data_source_block           7
_cod_original_cell_volume        2821.1(15)
_cod_database_code               4126794
_shelxl_version_number           2013-4
_shelx_res_checksum              36204
_shelx_hkl_checksum              50238