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_4126791
_publ_section_title
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 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_moiety         'C56 H58 Fe2 N2 P2 S2'
_chemical_formula_sum            'C56 H58 Fe2 N2 P2 S2'
_chemical_formula_weight         996.80
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-10-23
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 117.621(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3448(9)
_cell_length_b                   18.9750(14)
_cell_length_c                   12.4207(9)
_cell_measurement_reflns_used    3812
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.310
_cell_measurement_theta_min      2.834
_cell_volume                     2369.1(3)
_computing_cell_refinement       'SAINT V8.30C (?, 2016)'
_computing_data_reduction        'SAINT V8.30C (?, 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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13399
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         2.832
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0776 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.8019.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       block
_exptl_crystal_F_000             1044
_refine_diff_density_max         1.036
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0582
_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^)+(0.0378P)^2^+5.9600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1384
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3228
_reflns_number_total             5129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b11416_si_002.cif
_cod_data_source_block           1
_cod_database_code               4126791
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C13(H13), C12(H12), C28(H28), C27(H27), C26(H26),
 C25(H25), C24(H24), C18(H18), C22(H22), C21(H21), C20(H20), C19(H19)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C),
 C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'