Copper-catalyzed tandem cis-carbometallation/cyclization of imine-ynamides with arylboronic acids.
Wang, Hao-Ran; Huang, En-He; Luo, Chen; Luo, Wen-Feng; Xu, Yin; Qian, Peng-Cheng; Zhou, Jin-Mei; Ye, Long-Wu; Chemical communications (Cambridge, England) 56 (2020) 4832–4835; doi:10.1039/d0cc01424a

data_7126265
_publ_section_title
;
 Copper-catalyzed tandem cis-carbometallation/cyclization of
 imine-ynamides with arylboronic acids.
;
_journal_issue                   35
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4832
_journal_page_last               4835
_journal_paper_doi               10.1039/d0cc01424a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C28 H23 N O3 S'
_chemical_formula_sum            'C28 H23 N O3 S'
_chemical_formula_weight         453.53
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-14 deposited with the CCDC.	2020-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.9340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.77990(10)
_cell_length_b                   10.15360(10)
_cell_length_c                   18.2019(2)
_cell_measurement_reflns_used    9807
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      73.3160
_cell_measurement_theta_min      3.7220
_cell_volume                     2234.12(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'SIR2004 (Burla et al.,  2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.947
_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    -44.00   7.00   0.50    0.05    --  -47.72  15.00  27.00  102
  2  \w    -59.00  15.00   0.50    0.05    --  -47.72  37.00  60.00  148
  3  \w     54.00  79.00   0.50    0.05    --   47.72  15.00  27.00   50
  4  \w    125.00 160.00   0.50    0.05    --   99.94  15.00  27.00   70
  5  \w     86.00 120.00   0.50    0.05    --   99.94  15.00  27.00   68
  6  \w     65.00  91.00   0.50    0.05    --   99.94 -99.00  60.00   52
  7  \w     28.00  61.00   0.50    0.05    --   99.94 -99.00  60.00   66
  8  \w     27.00 111.00   0.50    0.05    --   99.94 -37.00  60.00  168
  9  \w     43.00  96.00   0.50    0.05    --   99.94 -99.00-120.00  106
 10  \w     25.00  97.00   0.50    0.05    --   99.94 -15.00-143.00  144
 11  \w     -7.00  18.00   0.50    0.05    --   47.72 -15.00-143.00   50
 12  \w   -110.00 -34.00   0.50    0.05    --  -47.72 -15.00-143.00  152
 13  \w   -124.00 -75.00   0.50    0.05    --  -86.25 -15.00-143.00   98
 14  \w   -155.00 -89.00   0.50    0.05    --  -86.25 -99.00 -90.00  132
 15  \w    -80.00 -55.00   0.50    0.05    --  -86.25  15.00  27.00   50
 16  \w    -87.00 -18.00   0.50    0.05    --  -86.25  37.00 150.00  138
 17  \w    -91.00 -14.00   0.50    0.05    --  -86.25 125.00 120.00  154
 18  \w     32.00  98.00   0.50    0.05    --   99.94 -99.00 150.00  132
;
_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      -0.1116931000
_diffrn_orient_matrix_UB_12      0.0153753000
_diffrn_orient_matrix_UB_13      0.0144243000
_diffrn_orient_matrix_UB_21      -0.0613755000
_diffrn_orient_matrix_UB_22      -0.0249726000
_diffrn_orient_matrix_UB_23      -0.0868449000
_diffrn_orient_matrix_UB_31      -0.0012963000
_diffrn_orient_matrix_UB_32      -0.1488343000
_diffrn_orient_matrix_UB_33      0.0160305000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15426
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.454
_diffrn_reflns_theta_min         3.656
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.537
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetate'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0530P)^2^+1.4270P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1112
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3907
_reflns_number_total             4263
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01424a2.cif
_cod_data_source_block           exp_7258
_cod_depositor_comments
'Adding full bibliography for 7126264--7126265.cif.'
_cod_database_code               7126265
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24),
  C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              29054
_shelx_hkl_checksum              64421
_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 1.226
_oxdiff_exptl_absorpt_empirical_full_min 0.758