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_4514671
_publ_section_title
;
 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
;
_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            'C25 H19 N O2'
_chemical_formula_weight         365.41
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 100.839(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6269(10)
_cell_length_b                   10.8792(7)
_cell_length_c                   22.0724(15)
_cell_measurement_reflns_used    9030
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      26.3766
_cell_measurement_theta_min      2.2946
_cell_volume                     3685.5(4)
_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      99(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_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  0.0503
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            54083
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.442
_diffrn_reflns_theta_min         1.327
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.9032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0552P)^2^+0.9942P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5957
_reflns_number_total             7578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02323_si_004.cif
_cod_data_source_block           mo_180524LT_0m
_cod_depositor_comments
;
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 

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C50 H38 N2 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     730.82
_cod_database_code               4514671
_shelxl_version_number           2014/6
_shelx_res_checksum              60383
_shelx_hkl_checksum              32126