Selective Synthesis of Multifunctionalized 2,3-Dihydroinden-1-ones and 1,3-Dihydroisobenzofurans from the Reaction of o-Alkynylbenzaldehydes with Imines Steered by N-Heterocyclic Carbene/Copper(II) and N-Heterocyclic Carbene/Base Cascade Catalysis.
Ding, Ya-Li; Li, Shi-Ning; Cheng, Ying; The Journal of organic chemistry 83 (2018) 8971–8983; doi:10.1021/acs.joc.8b01163

data_4035364
_publ_section_title
;
 Selective Synthesis of Multifunctionalized 2,3-Dihydroinden-1-ones and
 1,3-Dihydroisobenzofurans from the Reaction of o-Alkynylbenzaldehydes
 with Imines Steered by N-Heterocyclic Carbene/Copper(II) and
 N-Heterocyclic Carbene/Base Cascade Catalysis.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8971
_journal_page_last               8983
_journal_paper_doi               10.1021/acs.joc.8b01163
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C24 H19 N O2'
_chemical_formula_sum            'C24 H19 N O2'
_chemical_formula_weight         353.40
_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   geom
_audit_creation_date             2017-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.4813(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.04977(19)
_cell_length_b                   9.47578(13)
_cell_length_c                   16.4721(3)
_cell_measurement_reflns_used    6081
_cell_measurement_temperature    199.89(17)
_cell_measurement_theta_max      72.6150
_cell_measurement_theta_min      4.3390
_cell_volume                     1872.20(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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      199.89(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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    -50.00 -15.00   1.00    1.00    --  -41.49 -77.00-120.00   35
  2  \w    -72.00 -17.00   1.00    1.00    --  -41.49 -77.00 -30.00   55
  3  \w      1.00  82.00   1.00    1.00    --   41.49 -99.00  90.00   81
  4  \w     79.00 133.00   1.00    1.00    --  107.52 -30.00 120.00   54
  5  \w    106.00 178.00   1.00    1.00    --  107.52  45.00  90.00   72
  6  \w    127.00 176.00   1.00    1.00    --  107.52  30.00   0.00   49
  7  \w    131.00 178.00   1.00    1.00    --  107.52  30.00 -60.00   47
  8  \w     80.00 114.00   1.00    1.00    --  107.52  30.00   0.00   34
  9  \w     37.00 129.00   1.00    1.00    --  107.52 -30.00 -60.00   92
 10  \w     37.00 120.00   1.00    1.00    --  107.52-125.00 -30.00   83
 11  \w     34.00 139.00   1.00    1.00    --  107.52 -77.00 120.00  105
 12  \w     84.00 114.00   1.00    1.00    --  107.52-125.00 150.00   30
 13  \w     35.00  61.00   1.00    1.00    --  107.52-125.00 150.00   26
 14  \w     31.00  71.00   1.00    1.00    --  107.52 -30.00 120.00   40
 15  \w     31.00 138.00   1.00    1.00    --  107.52 -77.00 -30.00  107
 16  \w   -111.00 -30.00   1.00    1.00    --  -41.49 -37.00-150.00   81
 17  \w   -118.00 -92.00   1.00    1.00    --  -41.49 -77.00-120.00   26
 18  \w   -115.00 -18.00   1.00    1.00    --  -41.49 -37.00 120.00   97
;
_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      0.0770305000
_diffrn_orient_matrix_UB_12      -0.1036600000
_diffrn_orient_matrix_UB_13      -0.0398071000
_diffrn_orient_matrix_UB_21      -0.1027374000
_diffrn_orient_matrix_UB_22      -0.0766911000
_diffrn_orient_matrix_UB_23      -0.0419008000
_diffrn_orient_matrix_UB_31      0.0011448000
_diffrn_orient_matrix_UB_32      0.0991200000
_diffrn_orient_matrix_UB_33      -0.0740552000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.390
_diffrn_reflns_theta_min         4.354
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0539P)^2^+0.5524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3115
_reflns_number_total             3708
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01163_si_004.cif
_cod_data_source_block           20170516d
_cod_database_code               4035364
_chemical_oxdiff_formula         C1H1N1O1S1
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11),
 C12(H12), C13(H13), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_shelx_res_checksum              13705
_shelx_hkl_checksum              23617
_shelx_shelxl_version_number     2014/7
_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 2.093
_oxdiff_exptl_absorpt_empirical_full_min 0.798