Rh-Catalyzed Intermolecular Reactions of Cyclic α-Diazocarbonyl Compounds with Selectivity over Tertiary C-H Bond Migration
Andrew DeAngelis; Olga Dmitrenko; Joseph M. Fox; Journal of the American Chemical Society 134 (2012) 11035–11043; doi:10.1021/ja3046712

data_4118196
_publ_section_title
;
 Rh-Catalyzed Intermolecular Reactions of Cyclic \a-Diazocarbonyl
 Compounds with Selectivity over Tertiary C-H Bond Migration
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11035
_journal_page_last               11043
_journal_paper_doi               10.1021/ja3046712
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C21 H23 N O3'
_chemical_formula_weight         337.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.98(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.291(7)
_cell_length_b                   14.645(8)
_cell_length_c                   9.589(6)
_cell_measurement_reflns_used    369
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      13.84
_cell_measurement_theta_min      2.18
_cell_volume                     1709.3(17)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_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  0.6611
_diffrn_reflns_av_sigmaI/netI    0.3597
_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       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17891
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9972
_exptl_absorpt_correction_T_min  0.9863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.2530
_refine_ls_R_factor_gt           0.0915
_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^)+(0.0644P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1813
_refine_ls_wR_factor_ref         0.2772
_reflns_number_gt                806
_reflns_number_total             3012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3046712_si_003.cif
_cod_data_source_block           joef096a
_cod_original_cell_volume        1709.4(17)
_cod_database_code               4118196