Visible-Light-Driven Copper-Catalyzed Aerobic Oxidative Cascade Cyclization of N-Tosylhydrazones and Terminal Alkynes: Regioselective Synthesis of 3-Arylcoumarins
Ragupathi, Ayyakkannu; Sagadevan, Arunachalam; Charpe, Vaibhav Pramod; Lin, Chun-Cheng; Hwu, Jih Ru; Hwang, Kuo Chu; Chemical Communications  (2019) –; doi:10.1039/C9CC01801H

data_7123255
_publ_section_title
;
 Visible-Light-Driven Copper-Catalyzed Aerobic Oxidative Cascade
 Cyclization of N-Tosylhydrazones and Terminal Alkynes: Regioselective
 Synthesis of 3-Arylcoumarins
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01801H
_journal_year                    2019
_chemical_formula_sum            'C16 H9 N O2'
_chemical_formula_weight         247.24
_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
_audit_update_record
;
2018-05-03 deposited with the CCDC.    2019-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.255(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.795(7)
_cell_length_b                   7.246(4)
_cell_length_c                   12.168(6)
_cell_measurement_reflns_used    1598
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.9207
_cell_measurement_theta_min      3.0612
_cell_volume                     1173.4(11)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
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_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)
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_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.970
_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  0.0741
_diffrn_reflns_av_unetI/netI     0.0759
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.970
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_diffrn_reflns_limit_h_min       -17
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_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10299
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_min         1.530
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.7321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.371
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_refine_ls_extinction_coef       0.028(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.0912
_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^)+(0.1451P)^2^+1.6899P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2398
_refine_ls_wR_factor_ref         0.2722
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1431
_reflns_number_total             2329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01801h2.cif
_cod_data_source_block           170811LT_a
_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 
;
_cod_original_cell_volume        1173.5(10)
_cod_database_code               7123255
_shelxl_version_number           2014/6
_shelx_res_checksum              33872