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_4126793
_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         'C37 H36 Fe N P S'
_chemical_formula_sum            'C37 H36 Fe N P S'
_chemical_formula_weight         613.55
_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     dual
_audit_creation_date             2017-10-19
_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                 106.209(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.803(4)
_cell_length_b                   9.7913(11)
_cell_length_c                   15.7087(17)
_cell_measurement_reflns_used    2487
_cell_measurement_temperature    192.99(10)
_cell_measurement_theta_max      75.4010
_cell_measurement_theta_min      4.3820
_cell_volume                     3072.5(8)
_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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      192.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.973
_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     52.00  78.00   2.00    4.00    --   48.45  61.00 -17.00   13
  2  \w     92.00 146.00   2.00   20.00    --  107.75  61.00 -17.00   27
  3  \w    149.00 175.00   2.00   20.00    --  107.75  61.00 -17.00   13
  4  \w    101.00 177.00   2.00   20.00    --  107.75  37.00 -90.00   38
  5  \w     97.00 171.00   2.00   20.00    --  107.75  19.00-120.00   37
  6  \w     92.00 174.00   2.00   20.00    --  107.75 125.00 -90.00   41
  7  \w     35.00 123.00   2.00   20.00    --  107.75 -61.00-156.00   44
  8  \w     36.00 110.00   2.00   20.00    --  107.75 -99.00  60.00   37
  9  \w     -5.00  49.00   2.00    4.00    --   48.45 -61.00-156.00   27
 10  \w    -65.00  19.00   2.00    4.00    --  -48.45  61.00 -17.00   42
 11  \w    -59.00 -19.00   2.00   20.00    --  -86.25  61.00 -17.00   20
 12  \w   -120.00 -32.00   2.00    4.00    --  -48.45 -61.00-156.00   44
 13  \w   -120.00 -72.00   2.00    4.00    --  -48.45-125.00 -30.00   24
 14  \w   -159.00 -85.00   2.00   20.00    --  -86.25 -61.00-156.00   37
;
_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      -0.0761476000
_diffrn_orient_matrix_UB_12      -0.0068592000
_diffrn_orient_matrix_UB_13      -0.0433459000
_diffrn_orient_matrix_UB_21      -0.0107809000
_diffrn_orient_matrix_UB_22      0.1121850000
_diffrn_orient_matrix_UB_23      0.0633668000
_diffrn_orient_matrix_UB_31      0.0061625000
_diffrn_orient_matrix_UB_32      0.1101604000
_diffrn_orient_matrix_UB_33      -0.0672812000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_av_unetI/netI     0.1050
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17209
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.051
_diffrn_reflns_theta_min         4.427
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.256
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80884
_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_colour            black
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             1288
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.082
_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     375
_refine_ls_number_reflns         5330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0571
_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^)+(0.0423P)^2^+4.7298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3259
_reflns_number_total             5330
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b11416_si_002.cif
_cod_data_source_block           6
_cod_database_code               4126793
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 96.42
_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:
 C12(H12), C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29),
  C31(H31), C32(H32), C33(H33), C34(H34), C36(H36), C37(H37)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C)
;
_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 1.586
_oxdiff_exptl_absorpt_empirical_full_min 0.613