Synthesis of Isocoumarin Derivatives via the Copper-Catalyzed Tandem Sequential Cyclization of 2- Halo-N-phenyl Benzamides and Acyclic 1,3-Diketones
Veerababurao Kavala; Cheng-Chuan Wang; Deepak Kumar Barange; Chun-Wei Kuo; Po-Min Lei; Ching-Fa Yao; Journal of Organic Chemistry 77 (2012) 5022–5029; doi:10.1021/jo300501j

data_4027225
_publ_section_title
;
 Synthesis of Isocoumarin Derivatives via the Copper-Catalyzed Tandem
 Sequential Cyclization of 2- Halo-N-phenyl Benzamides and Acyclic
 1,3-Diketones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5022
_journal_page_last               5029
_journal_paper_doi               10.1021/jo300501j
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C13 H9 N O2'
_chemical_formula_sum            'C13 H9 N O2'
_chemical_formula_weight         211.21
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.494(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2300(3)
_cell_length_b                   11.8600(4)
_cell_length_c                   11.2760(5)
_cell_measurement_reflns_used    9584
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     960.69(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5455
_diffrn_reflns_theta_full        25.13
_diffrn_reflns_theta_max         25.13
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9659
_exptl_absorpt_correction_T_min  0.9453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1307P)^2^+0.3673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1805
_refine_ls_wR_factor_ref         0.2005
_reflns_number_gt                2509
_reflns_number_total             3077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300501j_si_004.cif
_cod_data_source_block           13106
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027225