Cu-Catalyzed Reaction of 1,2-Dihalobenzenes with 1,3-Cyclohexanediones for the Synthesis of 3,4-Dihydrodibenzo[b,d]furan-1(2H)-ones
Nayyef Aljaar; Chandi C. Malakar; Jürgen Conrad; Sabine Strobel; Thomas Schleid; Uwe Beifuss; Journal of Organic Chemistry 77 (2012) 7793–7803; doi:10.1021/jo3014275

data_4027519
_publ_section_title
;
 Cu-Catalyzed Reaction of 1,2-Dihalobenzenes with 1,3-Cyclohexanediones
 for the Synthesis of 3,4-Dihydrodibenzo[b,d]furan-1(2H)-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7793
_journal_page_last               7803
_journal_paper_doi               10.1021/jo3014275
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C13 H12 O2'
_chemical_formula_sum            'C13 H12 O2'
_chemical_formula_weight         200.23
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.0264(3)
_cell_length_b                   12.8797(3)
_cell_length_c                   14.4734(3)
_cell_measurement_reflns_used    2741
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      0.41
_cell_volume                     2055.46(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4536
_diffrn_reflns_theta_full        28.20
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         8.18
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9949
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Scalepack (W. Minor & Z. Otwinowski)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       platelet
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0695P)^2^+0.8642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1560
_refine_ls_wR_factor_ref         0.1716
_reflns_number_gt                1943
_reflns_number_total             2450
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3014275_si_001.cif
_cod_data_source_block           c:\crystal\x-red\beijul11
_cod_database_code               4027519