Organocatalytic enantioselective aza-Friedel-Crafts reaction between benzothiazolimines and 2-naphthols for the preparation of chiral 2'-aminobenzothiazolomethyl naphthols.
Li, Chen-Yi; Xiang, Min; Zhang, Jian; Li, Wen-Sheng; Zou, Ying; Tian, Fang; Wang, Li-Xin; Organic & biomolecular chemistry 19 (2021) 7690–7694; doi:10.1039/d1ob01443a

data_7158268
_publ_section_title
;
 Organocatalytic enantioselective aza-Friedel-Crafts reaction between
 benzothiazolimines and 2-naphthols for the preparation of chiral
 2'-aminobenzothiazolomethyl naphthols.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7690
_journal_page_last               7694
_journal_paper_doi               10.1039/d1ob01443a
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H18 N2 O S'
_chemical_formula_sum            'C24 H18 N2 O S'
_chemical_formula_weight         382.46
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-13 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.861(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.8325(3)
_cell_length_b                   15.6420(8)
_cell_length_c                   8.9374(5)
_cell_measurement_reflns_used    1909
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.7150
_cell_measurement_theta_min      4.9700
_cell_volume                     953.98(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -108.00 -32.00   1.00    1.00    --  -33.50 178.00 -90.00   76
  2  \w    -98.00 -54.00   1.00    1.00    --  -33.50 -77.00  30.00   44
  3  \w      0.00  27.00   1.00    1.00    --   36.47  19.00 -30.00   27
  4  \w      4.00  76.00   1.00    1.00    --   36.47 -99.00  60.00   72
  5  \w     31.00  99.00   1.00    1.00    --   36.47  19.00 -30.00   68
  6  \w      7.00  73.00   1.00    1.00    --   36.47 -99.00 -90.00   66
  7  \w     64.00  99.00   1.00    1.00    --   36.47 178.00-150.00   35
  8  \w     30.00  57.00   1.00    1.00    --   36.47 -99.00 -60.00   27
  9  \w     39.00  76.00   1.00    4.00    --  108.00 -45.00-180.00   37
 10  \w     38.00 112.00   1.00    4.00    --  108.00-111.00 -30.00   74
 11  \w     41.00 126.00   1.00    4.00    --  108.00 -45.00  90.00   85
 12  \w     77.00 108.00   1.00    4.00    --  108.00 -45.00-180.00   31
 13  \w     67.00 111.00   1.00    4.00    --  108.00-111.00  90.00   44
 14  \w     83.00 177.00   1.00    4.00    --  108.00  77.00-120.00   94
 15  \w     83.00 110.00   1.00    4.00    --  108.00 -77.00 120.00   27
 16  \w     51.00 145.00   1.00    4.00    --  108.00   0.00-150.00   94
 17  \w      6.00  35.00   1.00    3.50    --  -33.50  19.00  90.00   29
 18  \w    -33.00   2.00   1.00    3.50    --  -33.50  19.00  90.00   35
 19  \w    -30.00   0.00   1.00    3.50    --  -33.50  77.00-180.00   30
 20  \w     59.00 110.00   1.00    3.50    --   36.47 178.00-120.00   51
 21  \w     63.00 103.00   1.00    3.50    --   36.47  57.00  30.00   40
 22  \w     31.00  57.00   1.00    3.50    --   36.47 -99.00 -30.00   26
 23  \w    -31.00  12.00   1.00    3.50    --   36.47 -57.00-120.00   43
 24  \w     38.00  96.00   1.00    4.00    --  108.00 -30.00 150.00   58
 25  \w    106.00 134.00   1.00    4.00    --  108.00 -77.00-150.00   28
 26  \w     99.00 178.00   1.00    4.00    --  108.00  30.00 -30.00   79
 27  \w     79.00 109.00   1.00    4.00    --  108.00-111.00-150.00   30
 28  \w     69.00 101.00   1.00    4.00    --  108.00 -77.00-150.00   32
 29  \w     44.00 120.00   1.00    4.00    --  108.00 -45.00 -60.00   76
 30  \w     83.00 116.00   1.00    4.00    --  108.00 178.00-180.00   33
 31  \w     78.00 104.00   1.00    4.00    --  108.00 -94.00 -30.00   26
 32  \w    103.00 176.00   1.00    4.00    --  108.00  61.00 -90.00   73
 33  \w     61.00  97.00   1.00    4.00    --  108.00 -94.00 120.00   36
 34  \w     79.00 105.00   1.00    4.00    --  108.00 -61.00 -60.00   26
 35  \w     44.00  73.00   1.00    4.00    --  108.00 -61.00 -60.00   29
 36  \w    -68.00 -42.00   1.00    3.50    --  -33.50 178.00  30.00   26
 37  \w     52.00  77.00   1.00    3.50    --   36.47 -99.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0096907000
_diffrn_orient_matrix_UB_12      0.0973723000
_diffrn_orient_matrix_UB_13      -0.0252585000
_diffrn_orient_matrix_UB_21      -0.0064541000
_diffrn_orient_matrix_UB_22      0.0140975000
_diffrn_orient_matrix_UB_23      0.1702786000
_diffrn_orient_matrix_UB_31      0.2254394000
_diffrn_orient_matrix_UB_32      0.0046098000
_diffrn_orient_matrix_UB_33      0.0123784000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3412
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.955
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1118 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3412
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0506P)^2^+0.3141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1433
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2902
_reflns_number_total             3412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01443a2.cif
_cod_data_source_block           202011236_tw
_cod_depositor_comments          'Adding full bibliography for 7158268.cif.'
_cod_original_cell_volume        953.99(8)
_cod_database_code               7158268
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N4S1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.780
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.631(7)
 0.369(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 H1A-N1
 0.87 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C11(H11)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1B), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
  C16(H16), C17(H17), C24(H24), C23(H23), C22(H22), C21(H21)
4.c Fitted hexagon refined as free rotating group:
 C6(C1,C2,C3,C4,C5), C12(C13,C14,C15,C16,C17), C20(C19,C24,C23,C22,C21)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.156
_oxdiff_exptl_absorpt_empirical_full_min 0.877