Stereocontrolled Construction of Seven-Membered Carbocycles Using a Combination of Brook Rearrangement-Mediated [3 + 4] Annulation and Epoxysilane Rearrangement
Yoshio Nakai; Masatoshi Kawahata; Kentaro Yamaguchi; Kei Takeda; Journal of Organic Chemistry 72 (2007) 1379–1387; doi:10.1021/jo062282c

data_4022740
_publ_section_title
;
 Stereocontrolled Construction of Seven-Membered Carbocycles
 Using a Combination of Brook Rearrangement-Mediated [3 + 4] Annulation
 and Epoxysilane Rearrangement
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1379
_journal_page_last               1387
_journal_paper_doi               10.1021/jo062282c
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H27 Br O6'
_chemical_formula_sum            'C19 H27 Br O6'
_chemical_formula_weight         431.32
_chemical_name_systematic
; 
 ? 
;
_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                 90.048(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.191(2)
_cell_length_b                   32.813(10)
_cell_length_c                   8.726(3)
_cell_measurement_reflns_used    1116
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.10
_cell_measurement_theta_min      2.41
_cell_volume                     2059.0(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.2096
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7107
_diffrn_reflns_theta_full        27.72
_diffrn_reflns_theta_max         27.72
_diffrn_reflns_theta_min         1.24
_exptl_absorpt_coefficient_mu    2.026
_exptl_absorpt_correction_T_max  0.7509
_exptl_absorpt_correction_T_min  0.4979
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.043(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.793
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         7107
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.793
_refine_ls_R_factor_all          0.2017
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.056
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1620
_reflns_number_gt                2367
_reflns_number_total             7107
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062282csi20061105_110620.cif
_cod_data_source_block           YN-VIII-1476B
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022740