Asymmetric synthesis of benzothiazolopyrimidines with high catalytic efficiency and stereoselectivity under bifunctional phosphonium salt systems.
Lu, Dongming; Wu, Jia-Hong; Pan, Jianke; Chen, Xue; Ren, Xiaoyu; Wang, Tianli; Chemical communications (Cambridge, England) 56 (2020) 11231–11234; doi:10.1039/d0cc04820h

data_7127080
_publ_section_title
;
 Asymmetric synthesis of benzothiazolopyrimidines with high catalytic
 efficiency and stereoselectivity under bifunctional phosphonium salt
 systems.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11231
_journal_page_last               11234
_journal_paper_doi               10.1039/d0cc04820h
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H31 Cl N2 O4 S'
_chemical_formula_sum            'C32 H31 Cl N2 O4 S'
_chemical_formula_weight         575.10
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-11-20 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.0201(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.29029(17)
_cell_length_b                   20.9516(4)
_cell_length_c                   8.39594(16)
_cell_measurement_reflns_used    6782
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      71.7820
_cell_measurement_theta_min      4.1760
_cell_volume                     1447.40(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -104.00 -20.00   1.00    1.00    --  -36.42 -57.00-180.00   84
  2  \w   -106.00 -18.00   1.00    1.00    --  -36.42 -38.00 -90.00   88
  3  \w   -104.00 -20.00   1.00    1.00    --  -36.42 -57.00  90.00   84
  4  \w   -104.00 -20.00   1.00    1.00    --  -36.42 -57.00   0.00   84
  5  \w     23.00  90.00   1.00    1.00    --   36.42-125.00 -30.00   67
  6  \w    -31.00  53.00   1.00    1.00    --   36.42 -57.00 -60.00   84
  7  \w     23.00  90.00   1.00    1.00    --   36.42-125.00 150.00   67
  8  \w    100.00 176.00   1.00    1.95    --  106.21 111.00 150.00   76
  9  \w     37.00 109.00   1.00    1.95    --  106.21 -94.00 -60.00   72
 10  \w     38.00 124.00   1.00    1.95    --  106.21 -45.00  60.00   86
 11  \w     89.00 175.00   1.00    1.95    --  106.21  45.00   0.00   86
 12  \w     39.00 133.00   1.00    1.95    --  106.21 -77.00 150.00   94
 13  \w     89.00 175.00   1.00    1.95    --  106.21  45.00-180.00   86
 14  \w     36.00 113.00   1.00    1.95    --  106.21-111.00-120.00   77
 15  \w     36.00 113.00   1.00    1.95    --  106.21-111.00  90.00   77
 16  \w     37.00 109.00   1.00    1.95    --  106.21 -94.00  90.00   72
 17  \w     36.00 128.00   1.00    1.95    --  106.21 -30.00 150.00   92
 18  \w     36.00 128.00   1.00    1.95    --  106.21 -30.00-120.00   92
 19  \w     39.00 133.00   1.00    1.95    --  106.21 -77.00 -30.00   94
 20  \w     35.00 145.00   1.00    1.95    --  106.21 -15.00 -30.00  110
 21  \w    -53.00  31.00   1.00    1.00    --  -36.42  57.00-120.00   84
 22  \w    -55.00  33.00   1.00    1.00    --  -36.42  38.00  90.00   88
 23  \w     10.00 104.00   1.00    1.00    --   36.42  77.00  60.00   94
 24  \w    -33.00  29.00   1.00    1.00    --   36.42 -38.00  90.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0349219000
_diffrn_orient_matrix_UB_12      0.0722360000
_diffrn_orient_matrix_UB_13      0.0040305000
_diffrn_orient_matrix_UB_21      0.1827393000
_diffrn_orient_matrix_UB_22      -0.0136004000
_diffrn_orient_matrix_UB_23      0.0434525000
_diffrn_orient_matrix_UB_31      0.0214131000
_diffrn_orient_matrix_UB_32      -0.0016886000
_diffrn_orient_matrix_UB_33      -0.1796201000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13708
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.767
_diffrn_reflns_theta_min         4.220
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 2380 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5560
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0991P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1404
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                5331
_reflns_number_total             5560
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04820h2.cif
_cod_data_source_block           wtl-ldm-150k
_cod_depositor_comments          'Adding full bibliography for 7127080.cif.'
_cod_database_code               7127080
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00N(H00N)
2.b Secondary CH2 refined with riding coordinates:
 C00J(H00A,H00B), C00O(H00C,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00H(H00H), C00L(H00L), C00M(H00M), C00P(H00P), C00Q(H00Q),
 C00S(H00S), C00T(H00T), C00V(H00V), C00W(H00W), C010(H010), C011(H011),
 C013(H013)
2.d Idealised Me refined as rotating group:
 C00Y(H00G,H00I,H00J), C00Z(H00K,H00O,H00R), C012(H01A,H01B,H01C), C014(H01D,
 H01E,H01F)
;
_shelx_res_checksum              62535
_shelx_hkl_checksum              88781
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-11-20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.807
_oxdiff_exptl_absorpt_empirical_full_min 0.699