Asymmetric synthesis of β-amino ketones by using cinchona alkaloid-based chiral phase transfer catalysts.
Li, Weihua; Wang, Yifeng; Xu, Danqian; Organic & biomolecular chemistry 16 (2018) 8704–8709; doi:10.1039/c8ob02484g

data_7156548
_publ_section_title
;
 Asymmetric synthesis of \b-amino ketones by using cinchona alkaloid-based
 chiral phase transfer catalysts.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8704
_journal_page_last               8709
_journal_paper_doi               10.1039/c8ob02484g
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         C23H19FN2O2S
_chemical_formula_sum            'C46 H37 F2 N4 O4 S2'
_chemical_formula_weight         811.91
_chemical_name_systematic
'3-(2-Fluorophenyl)-3-((6-methoxybenzo[d]thiazol-2-yl)amino)-1-phenyl propan-1-one'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-09-15 deposited with the CCDC.
2018-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.434(7)
_cell_length_b                   10.662(10)
_cell_length_c                   44.27(4)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.37
_cell_volume                     3981(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            29211
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         2.120
_exptl_absorpt_coefficient_mu    0.194
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1692
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 2394 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         6998
_refine_ls_number_restraints     366
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+4.5197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6258
_reflns_number_total             6998
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02484g2.cif
_cod_data_source_block           20180907y03_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'AD' changed to 'ad'
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 7156548.cif.
;
_cod_database_code               7156548
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              59926
_shelx_hkl_checksum              74710