Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines: scope and limitations.
Stark, Daniel G.; Young, Claire M.; O'Riordan, Timothy J C; Slawin, Alexandra M. Z.; Smith, Andrew D.; Organic & biomolecular chemistry 14 (2016) 8068–8073; doi:10.1039/c6ob01473a

data_7155218
_publ_section_title
;
 Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis
 using saccharin-derived ketimines: scope and limitations.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8068
_journal_page_last               8073
_journal_paper_doi               10.1039/c6ob01473a
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H16 Br N O3 S, 0.5(C H Cl3)'
_chemical_formula_sum            'C23.5 H16.5 Br Cl1.5 N O3 S'
_chemical_formula_weight         526.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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_date             2016-07-07
_audit_creation_method           'by CrystalStructure 4.2'
_audit_update_record
;
2016-07-08 deposited with the CCDC.
2016-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.140(5)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   14.189(3)
_cell_length_b                   10.9261(18)
_cell_length_c                   14.233(3)
_cell_measurement_reflns_used    5892
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.30
_cell_measurement_theta_min      2.40
_cell_volume                     2203.2(8)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11136
_diffrn_reflns_point_group_measured_fraction_full 0.796
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.305
_diffrn_reflns_theta_min         2.351
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.174
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1060.00
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.91
_refine_diff_density_min         -0.50
_refine_ls_abs_structure_details
;
 Flack x determined using 1648 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     559
_refine_ls_number_reflns         6360
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0451P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.537
_reflns_Friedel_fraction_full    0.591
_reflns_Friedel_fraction_max     0.587
_reflns_number_gt                5304
_reflns_number_total             6360
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c6ob01473a2.cif
_cod_data_source_block           31
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'ad ' changed to 'ad'
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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155218.cif.

2017-03-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C47 H33 Br2 Cl3 N2 O6 S2'
_cod_original_formula_sum        'C47 H33 Br2 Cl3 N2 O6 S2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1052.07
_cod_database_code               7155218
_shelx_res_checksum              20623