Highly enantiospecific platinum-catalyzed cycloisomerizations: synthesis of enantioenriched oxabicycloheptene derivatives.
Newcomb, Eric T.; Ferreira, Eric M.; Organic letters 15 (2013) 1772–1775; doi:10.1021/ol400625f

data_1511933
_publ_section_title
;
 Highly enantiospecific platinum-catalyzed cycloisomerizations: synthesis
 of enantioenriched oxabicycloheptene derivatives.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1772
_journal_page_last               1775
_journal_paper_doi               10.1021/ol400625f
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H21 Br O'
_chemical_formula_weight         369.29
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 113.168(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.7086(4)
_cell_length_b                   10.3343(5)
_cell_length_c                   10.3919(5)
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.27
_cell_measurement_theta_min      2.54
_cell_volume                     859.82(7)
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'APEX2 (Bruker, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22316
_diffrn_reflns_theta_full        33.29
_diffrn_reflns_theta_max         33.29
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    2.393
_exptl_absorpt_correction_T_max  0.5447
_exptl_absorpt_correction_T_min  0.3011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.29
_refine_diff_density_max         1.630
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.022(6)
_refine_ls_extinction_method     constr
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         5869
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0277P)^2^+0.3650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0700
_reflns_number_gt                5534
_reflns_number_total             5869
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400625f_si_002.cif
_cod_data_source_block           ef09_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1511933