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_4035362
_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         'C29 H21 N O2'
_chemical_formula_sum            'C29 H21 N O2'
_chemical_formula_weight         415.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.6401(6)
_cell_length_b                   10.0875(2)
_cell_length_c                   21.1461(7)
_cell_measurement_reflns_used    4391
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.9870
_cell_measurement_theta_min      4.7470
_cell_volume                     4189.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (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      100.00(10)
_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 0.989
_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    -63.00  28.00   1.00    5.00    --  -39.74  19.00  90.00   91
  2  \w   -108.00 -15.00   1.00    5.00    --  -39.74 -57.00  90.00   93
  3  \w     86.00 128.00   1.00    5.00    --   39.74 178.00-180.00   42
  4  \w     88.00 154.00   1.00   10.00    --  107.19  45.00-150.00   66
  5  \w     82.00 178.00   1.00   10.00    --  107.19  45.00 -60.00   96
  6  \w     78.00 143.00   1.00   10.00    --  107.19  61.00  60.00   65
  7  \w     74.00 101.00   1.00   10.00    --  107.19 -45.00 120.00   27
  8  \w     34.00  73.00   1.00   10.00    --  107.19 -45.00 120.00   39
  9  \w     35.00 124.00   1.00   10.00    --  107.19 -77.00   0.00   89
 10  \w     28.00 107.00   1.00   10.00    --  107.19 -94.00 -30.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0106237000
_diffrn_orient_matrix_UB_12      -0.0441528000
_diffrn_orient_matrix_UB_13      0.0690230000
_diffrn_orient_matrix_UB_21      -0.0040300000
_diffrn_orient_matrix_UB_22      0.1462724000
_diffrn_orient_matrix_UB_23      0.0206663000
_diffrn_orient_matrix_UB_31      -0.0776239000
_diffrn_orient_matrix_UB_32      -0.0017600000
_diffrn_orient_matrix_UB_33      -0.0104691000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15731
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.211
_diffrn_reflns_theta_min         4.181
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       needle
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0468P)^2^+1.4067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3434
_reflns_number_total             4158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01163_si_003.cif
_cod_data_source_block           20160730c
_cod_original_cell_volume        4189.4(2)
_cod_database_code               4035362
_chemical_oxdiff_formula         c1h1n1o1
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C25(H25), C26(H26), C27(H27), C28(H28), C29(H29)
;
_shelx_res_checksum              98394
_shelx_hkl_checksum              84158
_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 1.721
_oxdiff_exptl_absorpt_empirical_full_min 0.474