Highly enantioselective [4 + 2] cycloadditions of allenoates and dual activated olefins catalyzed by N-acyl aminophosphines.
Xiao, Hua; Chai, Zhuo; Cao, Dongdong; Wang, Hongyu; Chen, Jinghao; Zhao, Gang; Organic & biomolecular chemistry 10 (2012) 3195–3201; doi:10.1039/c2ob25295c

data_7152300
_publ_section_title
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 Highly enantioselective [4 + 2] cycloadditions of allenoates and dual
 activated olefins catalyzed by N-acyl aminophosphines.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3195
_journal_page_last               3201
_journal_paper_doi               10.1039/c2ob25295c
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H24 Br N O6'
_chemical_formula_weight         478.33
_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                 101.055(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1070(11)
_cell_length_b                   12.1050(16)
_cell_length_c                   11.6138(16)
_cell_measurement_reflns_used    2144
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      44.472
_cell_measurement_theta_min      4.909
_cell_volume                     1118.6(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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0667
_diffrn_reflns_av_sigmaI/netI    0.0735
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6158
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    1.874
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.0946
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.017(13)
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4065
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0774P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                2675
_reflns_number_total             4065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25295c.txt
_cod_data_source_block           cd201394
_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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7152300