Hydroboration and reductive amination of ketones and aldehydes with HBpin by a bench stable Pd(II)-catalyst.
Mahato, Shreya; Rawal, Parveen; Devadkar, Ajitrao Kisan; Joshi, Mayank; Roy Choudhury, Angshuman; Biswas, Bhaskar; Gupta, Puneet; Panda, Tarun K.; Organic & biomolecular chemistry 20 (2022) 1103–1111; doi:10.1039/d1ob02339j

data_7158479
_publ_section_title
;
 Hydroboration and reductive amination of ketones and aldehydes with HBpin
 by a bench stable Pd(II)-catalyst.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1103
_journal_page_last               1111
_journal_paper_doi               10.1039/d1ob02339j
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C20 H14 N2 O2 Pd'
_chemical_formula_sum            'C20 H14 N2 O2 Pd'
_chemical_formula_weight         420.73
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-19 deposited with the CCDC.	2022-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3533(4)
_cell_length_b                   16.8012(8)
_cell_length_c                   17.7277(12)
_cell_measurement_reflns_used    1958
_cell_measurement_temperature    298.0(2)
_cell_measurement_theta_max      23.5700
_cell_measurement_theta_min      2.6030
_cell_volume                     1594.46(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (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_temperature      298.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.956
_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    -69.00 118.20   0.30   30.00    --   29.89  54.00 -30.00  624
  2  \w     14.00  39.80   0.30   30.00    --   29.89  54.00 -30.00   86
  3  \w    -69.00  65.10   0.30   30.00    --   29.89  54.00  30.00  447
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0311455000
_diffrn_orient_matrix_UB_12      0.0386684000
_diffrn_orient_matrix_UB_13      0.0130107000
_diffrn_orient_matrix_UB_21      0.0161678000
_diffrn_orient_matrix_UB_22      -0.0151706000
_diffrn_orient_matrix_UB_23      0.0369997000
_diffrn_orient_matrix_UB_31      0.1277791000
_diffrn_orient_matrix_UB_32      -0.0075460000
_diffrn_orient_matrix_UB_33      -0.0078916000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_unetI/netI     0.1666
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13717
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.763
_diffrn_reflns_theta_min         2.598
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.213
_refine_diff_density_min         -0.996
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details
;
 Flack x determined using 554 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1902
_refine_ls_R_factor_gt           0.0698
_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^)+(0.0532P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1852
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                2352
_reflns_number_total             5493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02339j2.cif
_cod_data_source_block           ml1_pd_rt
_cod_depositor_comments          'Adding full bibliography for 7158479.cif.'
_cod_database_code               7158479
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C7(H7), C16(H16), C2(H2), C12(H12), C9(H9), C4(H4), C19(H19),
 C11(H11), C17(H17), C5(H5), C18(H18), C3(H3), C10(H10)
;
_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 2.192
_oxdiff_exptl_absorpt_empirical_full_min 0.660