Chiral Phosphoric Acid-Catalyzed Enantioselective Construction of Structurally Diverse Benzothiazolopyrimidines
JARRIGE , Lucie; Glavač, Danijel; Levitre, Guillaume; Retailleau, Pascal; Bernadat, Guillaume; Neuville, luc; Masson, Geraldine; Chemical Science  (2019) –; doi:10.1039/C8SC05581E

data_1550579
_publ_section_title
;
 Chiral Phosphoric Acid-Catalyzed Enantioselective Construction of
 Structurally Diverse Benzothiazolopyrimidines
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC05581E
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H24 Br N3 O3 S'
_chemical_formula_sum            'C26 H24 Br N3 O3 S'
_chemical_formula_weight         538.45
_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_Hall           'P 6c'
_space_group_name_H-M_alt        'P 63'
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2018-01-08 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   17.660(2)
_cell_length_b                   17.660(2)
_cell_length_c                   13.5994(11)
_cell_measurement_reflns_used    291
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      46.9
_cell_measurement_theta_min      12.4
_cell_volume                     3673.1(7)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      213(2)
_diffrn_detector                 'Rigaku Rapid2 IP'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device
;
Crystal Goniometer chi partial
;
_diffrn_measurement_device_type  'Rigaku mm007HF Rapid2'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_radiation_monochromator  'Osmic CMF Confocal mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15330
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_min         2.889
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    3.358
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Reqab (Higashi-Rigaku,1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       needle
_exptl_crystal_F_000             1656
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 727 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4300
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0330P)^2^+3.6724P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2314
_reflns_number_total             4302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc05581e2.cif
_cod_data_source_block           jha1219b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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 
;
_cod_original_cell_volume        3673.1(9)
_cod_database_code               1550579
_shelx_shelxl_version_number     2018/1
_shelx_res_checksum              83374