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_4022827
_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_formula_sum            'C18 H20 O3'
_chemical_formula_weight         284.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                   17.283(2)
_cell_length_b                   22.136(3)
_cell_length_c                   7.4999(9)
_cell_measurement_reflns_used    899
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      28.75
_cell_measurement_theta_min      3.00
_cell_volume                     2869.2(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0889
_diffrn_reflns_av_sigmaI/netI    0.0686
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            19307
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9341
_exptl_absorpt_correction_T_min  0.8974
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0007(2)
_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   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          5.675
_refine_ls_shift/su_mean         0.123
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1180
_reflns_number_gt                1743
_reflns_number_total             2533
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0625711si20070213_111404.cif
_cod_data_source_block           w1194m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_database_code               4022827