Copper-Catalyzed [4+2]-Cycloadditions of Isoxazoles with 2-Alkynylbenzaldehydes To Access Distinct α-Carbonylnaphthalene Derivatives: C(3,4)- versus C(4,5)-Regioselectivity at Isoxazoles
Giri, Sovan Sundar; Liu, Rai-Shung; ACS Catalysis 9 (2019) 7328–; doi:10.1021/acscatal.9b02323

data_4514670
_publ_section_title
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 Copper-Catalyzed [4+2]-Cycloadditions of Isoxazoles with
 2-Alkynylbenzaldehydes To Access Distinct \a-Carbonylnaphthalene
 Derivatives: C(3,4)- versus C(4,5)-Regioselectivity at Isoxazoles
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_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              7328
_journal_paper_doi               10.1021/acscatal.9b02323
_journal_volume                  9
_journal_year                    2019
_chemical_formula_sum            'C22 H20 O2'
_chemical_formula_weight         316.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 98.987(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8408(8)
_cell_length_b                   13.1420(7)
_cell_length_c                   16.3982(9)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.4010
_cell_measurement_theta_min      2.2728
_cell_volume                     3371.9(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28225
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.408
_diffrn_reflns_theta_min         2.024
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.9057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lump
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0473P)^2^+2.7082P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0960
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3074
_reflns_number_total             3467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02323_si_003.cif
_cod_data_source_block           mo_180345lt_0m
_cod_depositor_comments
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The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
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_cod_database_code               4514670
_shelxl_version_number           2014/6
_shelx_res_checksum              25641
_shelx_hkl_checksum              18362