Enantioselective Synthesis of Functionalized Fluorinated Cyclohexenones via Robinson Annulation Catalyzed by Primary-Secondary Diamines
Hai-Feng Cui; Ying-Quan Yang; Zhuo Chai; Peng Li; Chang-Wu Zheng; Shi-Zheng Zhu; Gang Zhao; Journal of Organic Chemistry 75 (2010) 117–122; doi:10.1021/jo902081w

data_4025129
_publ_section_title
;
 Enantioselective Synthesis of Functionalized Fluorinated Cyclohexenones
 via Robinson Annulation Catalyzed by Primary-Secondary Diamines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              117
_journal_page_last               122
_journal_paper_doi               10.1021/jo902081w
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H26 Br F O4'
_chemical_formula_weight         489.37
_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                 90.673(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.7647(15)
_cell_length_b                   7.3008(13)
_cell_length_c                   18.426(3)
_cell_measurement_reflns_used    2011
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.176
_cell_measurement_theta_min      5.124
_cell_volume                     1179.0(3)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0724
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6219
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    1.779
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6534
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.364
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3787
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1117P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1823
_reflns_number_gt                2338
_reflns_number_total             3787
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902081w_si_001.cif
_cod_data_source_block           cd2988
_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        1179.0(4)
_cod_database_code               4025129