New multifunctional chiral phosphines and BINOL derivatives co-catalyzed enantioselective aza-Morita-Baylis-Hillman reaction of 5,5-disubstituted cyclopent-2-enone and N-sulfonated imines.
Yang, Yuan-Liang; Wei, Yin; Shi, Min; Organic & biomolecular chemistry 10 (2012) 7429–7438; doi:10.1039/c2ob25932j

data_7152570
_publ_section_title
;
 New multifunctional chiral phosphines and BINOL derivatives co-catalyzed
 enantioselective aza-Morita-Baylis-Hillman reaction of 5,5-disubstituted
 cyclopent-2-enone and N-sulfonated imines.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7429
_journal_page_last               7438
_journal_paper_doi               10.1039/c2ob25932j
_journal_volume                  10
_journal_year                    2012
_chemical_formula_sum            'C31 H26 Br N O3 S'
_chemical_formula_weight         572.50
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.308(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.424(2)
_cell_length_b                   9.9313(18)
_cell_length_c                   20.607(4)
_cell_measurement_reflns_used    1236
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.731
_cell_measurement_theta_min      4.554
_cell_volume                     2745.1(8)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0744
_diffrn_reflns_av_sigmaI/netI    0.0898
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14978
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    1.606
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.0845
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.439
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5100
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1790
_refine_ls_R_factor_gt           0.0841
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0302P)^2^+8.1673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.1948
_reflns_number_gt                2317
_reflns_number_total             5100
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25932j.txt
_cod_data_source_block           cd212123
_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_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2744.9(9)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7152570