Synthesis of 6H-Dibenzo[b,d]pyran-6-ones Using the Inverse Electron Demand Diels-Alder Reaction
Ian R. Pottie; Penchal Reddy Nandaluru; Wendy L. Benoit; David O. Miller; Louise N. Dawe; Graham J. Bodwell; Journal of Organic Chemistry 76 (2011) 9015–9030; doi:10.1021/jo201775e

data_4026722
_publ_contact_author_address
;
Department of chemistry
Memorial University of Newfoundland
St. Johns, NL, A1B 3X7, Canada
;
_publ_contact_author_email       gbodwell@mun.ca
_publ_contact_author_fax         1-709-864-3702
_publ_contact_author_name        'Graham J. Bodwell'
_publ_contact_author_phone       1-709-864-8406
_publ_section_title
;
 Synthesis of 6H-Dibenzo[b,d]pyran-6-ones Using the Inverse Electron
 Demand Diels-Alder Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9015
_journal_page_last               9030
_journal_paper_doi               10.1021/jo201775e
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C27 H32 N O6, C H2 Cl2, Cl'
_chemical_formula_sum            'C28 H34 Cl3 N O6'
_chemical_formula_weight         586.94
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 108.9690(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   35.794(3)
_cell_length_b                   6.9906(5)
_cell_length_c                   22.8659(17)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.63
_cell_measurement_theta_min      23.77
_cell_volume                     5410.8(7)
_computing_cell_refinement       'Rigaku MSC Crystal Clear 1999'
_computing_data_collection       'Rigaku MSC Crystal Clear 1999'
_computing_data_reduction        'Rigaku MSC Crystal Clear 1999'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL-97 (Acta Cryst.2008, A64, 112-122)'
_computing_structure_solution    'SHELXL-97 (Acta Cryst.2008, A64, 112-122)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4/CCD'
_diffrn_measurement_method       \w
_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  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16127
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.9700
_exptl_absorpt_correction_T_min  0.8227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       needle
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+3.6471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                3694
_reflns_number_total             5514
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201775e_si_004.cif
_cod_data_source_block           ip-6-83c
_cod_database_code               4026722