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_4021800
_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         'C17 H13 Br O3'
_chemical_formula_sum            'C17 H13 Br O3'
_chemical_formula_weight         345.18
_chemical_melting_point          ?
_chemical_name_systematic
; 
 1-[4-Bromophenyl]-1a,6a-dihydro-1H-6-oxacyclopropa[a]indene-1-carboxylic 
 acid methyl ester 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0996(8)
_cell_length_b                   9.6184(9)
_cell_length_c                   16.7505(15)
_cell_measurement_reflns_used    8749
_cell_measurement_temperature    90.0(10)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     1466.1(2)
_computing_cell_refinement       'APEX2 (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics    'Diamond 3.0'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90.0(10)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14384
_diffrn_reflns_theta_full        26.94
_diffrn_reflns_theta_max         26.94
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    2.811
_exptl_absorpt_correction_T_max  0.53
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS v2.10; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0180
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0104P)^2^+0.0248P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0405
_refine_ls_wR_factor_ref         0.0412
_reflns_number_gt                2971
_reflns_number_total             3147
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060779gsi20060411_050924.cif
_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 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4021800