Highly efficient and generalized asymmetric synthesis of quaternary stereogenic carbon-containing β-amino indanones/indanoles via Mannich-type additions between 1-indanones and N-tert-butanesulfinylketimines.
Wu, Lingmin; Xie, Chen; Mei, Haibo; Soloshonok, Vadim A.; Han, Jianlin; Pan, Yi; Organic & biomolecular chemistry 12 (2014) 4620–4627; doi:10.1039/c4ob00489b

data_7153798
_publ_section_title
;
 Highly efficient and generalized asymmetric synthesis of quaternary
 stereogenic carbon-containing \b-amino indanones/indanoles via
 Mannich-type additions between 1-indanones and
 N-tert-butanesulfinylketimines.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4620
_journal_page_last               4627
_journal_paper_doi               10.1039/c4ob00489b
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H24 F N O2 S'
_chemical_formula_sum            'C21 H24 F N O2 S'
_chemical_formula_weight         373.47
_space_group_IT_number           170
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   16.1494(15)
_cell_length_b                   16.1494(15)
_cell_length_c                   15.1345(14)
_cell_measurement_reflns_used    7002
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.70
_cell_measurement_theta_min      2.52
_cell_volume                     3418.3(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18924
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.9667
_exptl_absorpt_correction_T_min  0.9575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_platon_squeeze_details
;
;
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0719P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                3532
_reflns_number_total             4008
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00489b2.cif
_cod_data_source_block           20130717aa_0m-sr
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
according to
/usr/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7153798.cif.
;
_cod_original_sg_symbol_H-M      'P6(5)   '
_cod_database_code               7153798