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_7126264
_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         'C32 H31 F N2 O4 S2'
_chemical_formula_sum            'C32 H31 F N2 O4 S2'
_chemical_formula_weight         590.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2020-01-14 deposited with the CCDC.	2020-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.5120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.55150(10)
_cell_length_b                   15.2491(2)
_cell_length_c                   15.9658(2)
_cell_measurement_reflns_used    9063
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.6790
_cell_measurement_theta_min      3.9950
_cell_volume                     2811.40(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.996
_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   -109.00 -49.00   0.50    0.05    --  -39.57-158.00 -46.00  120
  2  \w    -67.00 -30.00   0.50    0.05    --  -39.57 118.00-166.00   74
  3  \w    -86.00 -28.00   0.50    0.15    --  -94.50 158.00 -12.00  116
  4  \w   -120.00 -78.00   0.50    0.15    --  -94.50-118.00 107.00   84
  5  \w     31.00 113.00   0.50    0.15    --  102.40-118.00 107.00  164
  6  \w     98.00 139.00   0.50    0.15    --  102.40-158.00 -46.00   82
  7  \w     65.00  97.00   0.50    0.15    --  102.40-158.00 -46.00   64
  8  \w   -113.00 -15.00   0.50    0.05    --  -39.57 -57.00 -90.00  196
  9  \w   -112.00 -12.00   0.50    0.05    --  -39.57 -57.00   0.00  200
 10  \w     37.00  62.00   0.50    0.05    --   39.57-118.00 107.00   50
 11  \w     91.00 116.00   0.50    0.05    --   39.57 178.00-150.00   50
 12  \w   -173.00 -85.00   0.50    0.15    --  -94.50 -94.00-150.00  176
 13  \w   -155.00 -80.00   0.50    0.15    --  -94.50 -94.00 150.00  150
 14  \w    -91.00 -26.00   0.50    0.15    --  -94.50 125.00 120.00  130
 15  \w     92.00 178.00   0.50    0.15    --  102.40 125.00 150.00  172
 16  \w    146.00 177.00   0.50    0.15    --  102.40 125.00 120.00   62
 17  \w     23.00  66.00   0.50    0.15    --  102.40 -45.00  60.00   86
 18  \w    103.00 143.00   0.50    0.15    --  102.40 125.00 120.00   80
 19  \w     32.00 113.00   0.50    0.15    --  102.40-125.00 -60.00  162
 20  \w     98.00 129.00   0.50    0.15    --  102.40 -45.00  60.00   62
;
_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      0.0662015000
_diffrn_orient_matrix_UB_12      -0.0872682000
_diffrn_orient_matrix_UB_13      0.0099100000
_diffrn_orient_matrix_UB_21      0.1034150000
_diffrn_orient_matrix_UB_22      0.0491188000
_diffrn_orient_matrix_UB_23      0.0409108000
_diffrn_orient_matrix_UB_31      -0.0523913000
_diffrn_orient_matrix_UB_32      -0.0131464000
_diffrn_orient_matrix_UB_33      0.0868182000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17034
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.009
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.21a (Rigaku Oxford Diffraction, 2018)
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    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetate'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         4988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0477P)^2^+1.6475P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0933
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4629
_reflns_number_total             4988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01424a2.cif
_cod_data_source_block           exp_3841
_cod_depositor_comments
'Adding full bibliography for 7126264--7126265.cif.'
_cod_database_code               7126264
_shelxl_version_number           2013-2
_diffrn_oxdiff_ac3_digest_frames
;
015f2c2cba9087f531fd0df6fb1a043b3b001205dc8
;
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C5(H5)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C18(H18), C19(H19),
 C21(H21), C22(H22), C24(H24), C25(H25), C28(H28), C29(H29), C30(H30), C31(H31),
  C32(H32)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              50558
_shelx_hkl_checksum              62914
_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 1.246
_oxdiff_exptl_absorpt_empirical_full_min 0.834