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_4126795
_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_moiety         'C34 H36 Fe N P S'
_chemical_formula_sum            'C34 H36 Fe N P S'
_chemical_formula_weight         577.52
_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
_audit_creation_date             2017-11-23
_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                 91.771(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5491(4)
_cell_length_b                   9.8654(3)
_cell_length_c                   15.8227(3)
_cell_measurement_reflns_used    6324
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      76.4880
_cell_measurement_theta_min      4.4370
_cell_volume                     2894.08(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -83.00 -57.00   1.00    1.05    --  -86.25 110.00 -34.00   26
  2  \w    -88.00   2.00   1.00    0.26    --  -48.45 110.00 -34.00   90
  3  \w    -89.00 -63.00   1.00    1.05    --  -86.25 125.00 120.00   26
  4  \w    -54.00 -15.00   1.00    1.05    --  -86.25 125.00 120.00   39
  5  \w    115.00 140.00   1.00    1.05    --  107.75 110.00 -34.00   25
  6  \w     43.00 115.00   1.00    1.05    --  107.75-110.00-129.00   72
  7  \w     30.00  56.00   1.00    0.26    --   48.45-110.00-129.00   26
  8  \w     38.00 120.00   1.00    1.05    --  107.75-125.00  90.00   82
  9  \w     36.00 107.00   1.00    1.05    --  107.75 -99.00  90.00   71
 10  \w   -119.00 -70.00   1.00    0.26    --  -48.45-125.00 -60.00   49
 11  \w   -151.00 -82.00   1.00    1.05    --  -86.25-110.00-129.00   69
 12  \w   -116.00 -30.00   1.00    0.26    --  -48.45 -77.00-120.00   86
 13  \w    108.00 178.00   1.00    1.05    --  107.75  37.00  60.00   70
 14  \w     93.00 178.00   1.00    1.05    --  107.75  57.00  30.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0766193000
_diffrn_orient_matrix_UB_12      -0.0213443000
_diffrn_orient_matrix_UB_13      -0.0381222000
_diffrn_orient_matrix_UB_21      -0.0167957000
_diffrn_orient_matrix_UB_22      0.1511323000
_diffrn_orient_matrix_UB_23      0.0139668000
_diffrn_orient_matrix_UB_31      0.0273469000
_diffrn_orient_matrix_UB_32      0.0330079000
_diffrn_orient_matrix_UB_33      -0.0885802000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16605
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         26.704
_diffrn_reflns_theta_min         2.195
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_refine_diff_density_max         1.489
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0830
_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^)+21.8450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1802
_refine_ls_wR_factor_ref         0.1963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4600
_reflns_number_total             5660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b11416_si_002.cif
_cod_data_source_block           8
_cod_database_code               4126795
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CPSFeN
_reflns_odcompleteness_completeness 99.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C20(H20), C1(H1), C18(H18), C11(H11), C8(H8), C21(H21), C24(H24), C10(H10),
 C14(H14), C5(H5), C9(H9), C15(H15), C22(H22), C16(H16), C23(H23), C3(H3),
 C17(H17), C4(H4)
2.b Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C33(H33A,H33B,H33C), C32(H32A,H32B,H32C), C31(H31A,H31B,
 H31C), C30(H30A,H30B,H30C), C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.835
_oxdiff_exptl_absorpt_empirical_full_min 0.537