C6' steric bulk of cinchona alkaloid enables an enantioselective Michael addition/annulation sequence toward pyranopyrazoles.
Bao, Xiaoze; Wei, Shiqiang; Qu, Jingping; Wang, Baomin; Chemical communications (Cambridge, England) 54 (2018) 2028–2031; doi:10.1039/c8cc00154e

data_7121204
_publ_section_title
;
 C6' steric bulk of cinchona alkaloid enables an enantioselective Michael
 addition/annulation sequence toward pyranopyrazoles.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2028
_journal_page_last               2031
_journal_paper_doi               10.1039/c8cc00154e
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H23 Br N2 O2'
_chemical_formula_weight         511.40
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_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
_audit_update_record
;
2017-12-14 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.5630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.6759(3)
_cell_length_b                   10.3960(2)
_cell_length_c                   14.9375(2)
_cell_measurement_reflns_used    4986
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.498
_cell_measurement_theta_min      2.368
_cell_volume                     2376.03(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11664
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    1.760
_exptl_absorpt_correction_T_max  0.6877
_exptl_absorpt_correction_T_min  0.5253
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    'riding mode'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4157
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+0.2640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                3685
_reflns_number_total             4157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc00154e2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7121204.cif.
;
_cod_original_sg_symbol_H-M      'C2   '
_cod_database_code               7121204