Palladium-catalyzed primary amine-directed regioselective mono- and di-alkynylation of biaryl-2-amines.
Jiang, Guangbin; Hu, Weigao; Li, Jianxiao; Zhu, Chuanle; Wu, Wanqing; Jiang, Huanfeng; Chemical communications (Cambridge, England) 54 (2018) 1746–1749; doi:10.1039/c7cc09308j

data_7121171
_publ_section_title
;
 Palladium-catalyzed primary amine-directed regioselective mono- and
 di-alkynylation of biaryl-2-amines.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1746
_journal_page_last               1749
_journal_paper_doi               10.1039/c7cc09308j
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C40 H55 N Si2'
_chemical_formula_sum            'C40 H55 N Si2'
_chemical_formula_weight         606.03
_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     direct
_audit_creation_date             2017-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-07 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.174(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3730(8)
_cell_length_b                   7.7388(4)
_cell_length_c                   32.2857(16)
_cell_measurement_reflns_used    6173
_cell_measurement_temperature    105(8)
_cell_measurement_theta_max      28.9210
_cell_measurement_theta_min      3.9640
_cell_volume                     3768.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      105(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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      9.00  75.00   1.00    8.00    --   11.74  57.00  90.00   66
  2  \w    -13.00  56.00   1.00    8.00    --   11.74  37.00-120.00   69
  3  \w    -68.00   3.00   1.00    8.00    --   11.74 -19.00  90.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0334111000
_diffrn_orient_matrix_UB_12      -0.0070269000
_diffrn_orient_matrix_UB_13      -0.0184538000
_diffrn_orient_matrix_UB_21      -0.0331113000
_diffrn_orient_matrix_UB_22      0.0043186000
_diffrn_orient_matrix_UB_23      0.0125132000
_diffrn_orient_matrix_UB_31      -0.0010073000
_diffrn_orient_matrix_UB_32      0.0912781000
_diffrn_orient_matrix_UB_33      -0.0020141000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            16703
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.264
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.068
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.524
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         6618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0955
_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^)+(0.1382P)^2^+9.5009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2496
_refine_ls_wR_factor_ref         0.2730
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5006
_reflns_number_total             6618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09308j2.cif
_cod_data_source_block           exp_638
_cod_depositor_comments
'Adding full bibliography for 7121170--7121171.cif.'
_cod_database_code               7121171
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.979
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C32(H32), C29(H29), C9(H9), C26(H26), C12(H12), C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C36(H36), C40(H40), C37(H37), C38(H38), C39(H39), C23(H23),
 C20(H20), C21(H21), C22(H22)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C34(H34A,H34B,H34C), C13(H13A,H13B,H13C), C30(H30A,H30B,
 H30C), C33(H33A,H33B,H33C), C27(H27A,H27B,H27C), C11(H11A,H11B,H11C), C10(H10A,
 H10B,H10C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C),
 C28(H28A,H28B,H28C)
;
_olex2_date_sample_data_collection 2017-06-12
_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 1.332
_oxdiff_exptl_absorpt_empirical_full_min 0.747