Investigation into Factors Influencing Stereoselectivity in the Reactions of Heterocycles with Donor-Acceptor-Substituted Rhodium Carbenoids
Simon J. Hedley; Dominic L. Ventura; Paulina M. Dominiak; Cara L. Nygren; Huw M. L. Davies; Journal of Organic Chemistry 71 (2006) 5349–5356; doi:10.1021/jo060779g

data_4021798
_publ_section_title
;
 Investigation into Factors Influencing Stereoselectivity in the
 Reactions of Heterocycles with Donor-Acceptor-Substituted
 Rhodium Carbenoids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5349
_journal_page_last               5356
_journal_paper_doi               10.1021/jo060779g
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H13 Br O3'
_chemical_formula_sum            'C13 H13 Br O3'
_chemical_formula_weight         297.14
_chemical_name_systematic
; 
7-(4-Bromo-phenyl)-2-oxa-bicyclo[4.1.0]heptane-
7-carboxylic acid methyl ester
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.5390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2726(2)
_cell_length_b                   15.5701(5)
_cell_length_c                   10.5727(3)
_cell_measurement_reflns_used    8469
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      34.46
_cell_measurement_theta_min      2.61
_cell_volume                     1168.65(6)
_computing_cell_refinement       'APEX2 (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_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      90(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8826
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        'not measured'
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.510
_exptl_absorpt_correction_T_max  0.361
_exptl_absorpt_correction_T_min  0.278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS v2.10; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), 1418 Friedel pairs'
_refine_ls_abs_structure_Flack   0.011(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.0155
_refine_ls_R_factor_gt           0.0152
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0380
_refine_ls_wR_factor_ref         0.0380
_reflns_number_gt                2728
_reflns_number_total             2773
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060779gsi20060411_050849.cif
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4021798