Unusual Manganese(III)-Mediated Oxidative Free Radical Additions of 1,3-Dicarbonyl Compounds to Benzonorbornadiene and 7-Heterobenzonorbornadienes: Mechanistic Studies
Raşit Çalişkan; Mohamed Fadelalla Ali; Ertan Şahin; William H. Watson; Metin Balci; Journal of Organic Chemistry 72 (2007) 3353–3359; doi:10.1021/jo0625711

data_4022828
_publ_contact_author             'sahin, E.'
_publ_contact_author_email       ertan@atauni.edu.tr
_publ_section_title
;
 Unusual Manganese(III)-Mediated Oxidative Free Radical Additions
 of 1,3-Dicarbonyl Compounds to Benzonorbornadiene
 and 7-Heterobenzonorbornadienes: Mechanistic Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3353
_journal_page_last               3359
_journal_paper_doi               10.1021/jo0625711
_journal_volume                  72
_journal_year                    2007
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C21 H23 N1 O4'
_chemical_formula_sum            'C21 H23 N O4'
_chemical_formula_weight         353.4
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-12-05T19:02:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 113.587(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7608(5)
_cell_length_b                   20.7728(8)
_cell_length_c                   9.7588(5)
_cell_measurement_reflns_used    910
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.4492
_cell_measurement_theta_min      2.4793
_cell_measurement_wavelength     0.71073
_cell_volume                     1813.37(19)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_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
;
        ????
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device
;
        RAXIS conversion
;
_diffrn_measurement_method       dtcell.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0039
_diffrn_orient_matrix_UB_12      0.111
_diffrn_orient_matrix_UB_13      0.0131
_diffrn_orient_matrix_UB_21      0.0007
_diffrn_orient_matrix_UB_22      -0.0057
_diffrn_orient_matrix_UB_23      0.0478
_diffrn_orient_matrix_UB_31      0.104
_diffrn_orient_matrix_UB_32      0.0411
_diffrn_orient_matrix_UB_33      0.0033
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20250
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        30.61
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         5495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0895
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0682P)^2^+0.4986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.179
_refine_ls_wR_factor_ref         0.2055
_reflns_number_gt                3359
_reflns_number_total             5495
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0625711si20070213_111434.cif
_cod_data_source_block           shelxl374-3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022828