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_4126792
_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         'C19 H22 B N O2'
_chemical_formula_sum            'C19 H22 B N O2'
_chemical_formula_weight         307.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-09-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.8640(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.8368(3)
_cell_length_b                   12.6939(2)
_cell_length_c                   17.8201(3)
_cell_measurement_reflns_used    5854
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      70.8960
_cell_measurement_theta_min      4.9870
_cell_volume                     3344.10(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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    -12.00  13.00   1.00    1.00    --    0.00 -90.00-105.00   25
  2  \w     13.00  82.00   1.00    1.00    --   54.00 -77.00-150.00   69
  3  \w     56.00 116.00   1.00    1.00    --  108.00-111.00 -90.00   60
  4  \w     76.00 130.00   1.00    1.00    --  108.00 -63.00 -90.00   54
  5  \w     98.00 124.00   1.00    1.00    --  108.00 -50.00-150.00   26
  6  \w    110.00 159.00   1.00    1.00    --  108.00  25.00-150.00   49
  7  \w     98.00 161.00   1.00    1.00    --  108.00  63.00-120.00   63
  8  \w     62.00 122.00   1.00    1.00    --   54.00  57.00 -60.00   60
  9  \w     48.00 123.00   1.00    1.00    --   54.00  57.00-180.00   75
 10  \w     38.00 130.00   1.00    1.00    --  108.00 -50.00   0.00   92
 11  \w     73.00 130.00   1.00    1.00    --  108.00 -63.00 120.00   57
 12  \w     65.00 113.00   1.00    1.00    --  108.00 -77.00  30.00   48
 13  \w     18.00  57.00   1.00    1.00    --   54.00 -57.00 -60.00   39
 14  \w     42.00 107.00   1.00    1.00    --  108.00-111.00-180.00   65
 15  \w    -12.00  14.00   1.00    1.00    --    0.00  57.00-180.00   26
 16  \w    -62.00 -28.00   1.00    1.00    --    0.00 -57.00  30.00   34
 17  \w    -26.00  19.00   1.00    1.00    --    0.00 -57.00  30.00   45
 18  \w    -15.00  11.00   1.00    1.00    --   54.00 -57.00  30.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0517641000
_diffrn_orient_matrix_UB_12      0.0749617000
_diffrn_orient_matrix_UB_13      0.0564312000
_diffrn_orient_matrix_UB_21      -0.0074026000
_diffrn_orient_matrix_UB_22      -0.0815539000
_diffrn_orient_matrix_UB_23      0.0632580000
_diffrn_orient_matrix_UB_31      0.0900947000
_diffrn_orient_matrix_UB_32      -0.0495343000
_diffrn_orient_matrix_UB_33      -0.0187092000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12847
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.060
_diffrn_reflns_theta_min         2.989
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         6345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0593P)^2^+1.3707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5634
_reflns_number_total             6345
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b11416_si_002.cif
_cod_data_source_block           5h
_cod_depositor_comments
;

2020-05-25
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        3344.10(11)
_cod_original_formula_moiety     '2(C19 H22 B N O2)'
_cod_original_formula_sum        'C38 H44 B2 N2 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     614.37
_cod_database_code               4126792
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.834
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C20(H20),
 C21(H21), C22(H22), C23(H23), C27(H27), C28(H28), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,
 H38B,H38C)
;
_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 1.370
_oxdiff_exptl_absorpt_empirical_full_min 0.517