Reagent-Controlled Regiodivergent Resolution of Unsymmetrical Oxabicyclic Alkenes Using a Cationic Rhodium Catalyst
Robert Webster; Christian Böing; Mark Lautens; Journal of the American Chemical Society 131 (2009) 444–445; doi:10.1021/ja807942m

data_4103779
_publ_section_title
;
 Reagent-Controlled Regiodivergent Resolution of Unsymmetrical Oxabicyclic
 Alkenes Using a Cationic Rhodium Catalyst
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              444
_journal_page_last               445
_journal_paper_doi               10.1021/ja807942m
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C15 H17 F2 N O2'
_chemical_formula_sum            'C15 H17 F2 N O2'
_chemical_formula_weight         281.30
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2730(6)
_cell_length_b                   8.7412(8)
_cell_length_c                   20.8648(18)
_cell_measurement_reflns_used    11751
_cell_measurement_temperature    200
_cell_measurement_theta_max      72.46
_cell_measurement_theta_min      4.24
_cell_volume                     1326.5(2)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17361
_diffrn_reflns_theta_full        73.06
_diffrn_reflns_theta_max         73.06
_diffrn_reflns_theta_min         4.24
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_T_max  0.8434
_exptl_absorpt_correction_T_min  0.6579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details 'Flack H D (1983), 1046 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.06(16)
_refine_ls_extinction_coef       0.047(3)
_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   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0961P)^2^+0.1133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                2529
_reflns_number_total             2594
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja807942m_si_001.cif
_cod_data_source_block           loug10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to the
built-in table from CIF Core dictionary named 'cif_core.dic' version
2.4.1 from 2010-06-29 (22 times).

'_geom_angle_publ_flag' value 'Y'
changed to 'y' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (32
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4103779