A hybrid silylene-Pd catalyst: efficient C-N cross-coupling of sterically bulky amines and chiral amines.
Kaulage, Sandeep H.; Parvin, Nasrina; Khopade, Kishor V.; Khan, Shabana; Chemical communications (Cambridge, England) 60 (2024) 9958–9961; doi:10.1039/d4cc03108c

data_7133521
_publ_section_title
;
 A hybrid silylene-Pd catalyst: efficient C-N cross-coupling of sterically
 bulky amines and chiral amines.
;
_journal_issue                   73
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9958
_journal_page_last               9961
_journal_paper_doi               10.1039/d4cc03108c
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H21 N'
_chemical_formula_sum            'C28 H21 N'
_chemical_formula_weight         371.46
_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
_audit_creation_date             2024-08-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-08-08 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.6857(15)
_cell_length_b                   12.012(2)
_cell_length_c                   37.160(6)
_cell_measurement_reflns_used    8988
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.62
_cell_measurement_theta_min      3.57
_cell_volume                     3877.0(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1220
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            64151
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.833
_diffrn_reflns_theta_min         2.378
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_T_max  0.7266
_exptl_absorpt_correction_T_min  0.6387
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1772 before and 0.1065 after correction.
The Ratio of minimum to maximum transmission is 0.8790.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       Plates
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.268
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 2100 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(4)
_refine_ls_extinction_coef       0.00057(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         7843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0737
_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^)+(0.0040P)^2^+4.0502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1351
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                6422
_reflns_number_total             7843
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03108c2.cif
_cod_data_source_block           5c
_cod_depositor_comments
'Adding full bibliography for 7133516--7133523.cif.'
_cod_original_cell_volume        3877.1(11)
_cod_database_code               7133521
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C1(H1), C29(H29)
1.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), N2(H2), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
  C14(H14), C15(H15), C19(H19), C20(H20), C23(H23), C24(H24), C26(H26),
 C27(H27), C28(H28), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39),
  C40(H40), C42(H42), C43(H43), C47(H47), C48(H48), C51(H51), C52(H52),
 C53(H53), C55(H55), C56(H56)
1.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              92932
_shelx_hkl_checksum              37386
_olex2_submission_special_instructions 'No special instructions were received'