Highly Selective Ylide-Initiated Michael Addition/Cyclization Reaction for Synthesis of Cyclohexadiene Epoxide and Vinylcyclopropane Derivatives
Ben-Hu Zhu; Rui Zhou; Jun-Cheng Zheng; Xian-Ming Deng; Xiu-Li Sun; Qi Shen; Yong Tang; Journal of Organic Chemistry 75 (2010) 3454–3457; doi:10.1021/jo100306z

data_4025422
_publ_section_title
;
 Highly Selective Ylide-Initiated Michael Addition/Cyclization Reaction
 for Synthesis of Cyclohexadiene Epoxide and Vinylcyclopropane Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3454
_journal_page_last               3457
_journal_paper_doi               10.1021/jo100306z
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H17 Br O3'
_chemical_formula_weight         385.25
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 113.078(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.320(5)
_cell_length_b                   5.5127(10)
_cell_length_c                   13.832(2)
_cell_measurement_reflns_used    1528
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.592
_cell_measurement_theta_min      5.591
_cell_volume                     1776.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.1033
_diffrn_reflns_av_sigmaI/netI    0.1158
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5180
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    2.328
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54285
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.501
_exptl_crystal_size_mid          0.402
_exptl_crystal_size_min          0.157
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3595
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.866
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0816P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1558
_reflns_number_gt                2098
_reflns_number_total             3595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100306z_si_001.cif
_cod_data_source_block           cd28116
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1776.2(6)
_cod_database_code               4025422