Direct organocatalytic chemoselective synthesis of pharmaceutically active benzothiazole/benzoxazole-triazoles.
Gorachand, Badaraita; Lakshmi, Pandhiti R.; Ramachary, Dhevalapally B.; Organic & biomolecular chemistry 23 (2025) 2142–2152; doi:10.1039/d4ob01527d

data_7160335
_publ_section_title
;
 Direct organocatalytic chemoselective synthesis of pharmaceutically
 active benzothiazole/benzoxazole-triazoles.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2142
_journal_page_last               2152
_journal_paper_doi               10.1039/d4ob01527d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C22 H16 N4 S'
_chemical_formula_sum            'C22 H16 N4 S'
_chemical_formula_weight         368.45
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-11
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2024-09-17 deposited with the CCDC.	2025-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8739(2)
_cell_length_b                   12.2152(6)
_cell_length_c                   25.4655(13)
_cell_measurement_reflns_used    4329
_cell_measurement_temperature    297.5(4)
_cell_measurement_theta_max      22.9330
_cell_measurement_theta_min      2.2870
_cell_volume                     1827.17(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (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      air
_diffrn_ambient_temperature      297.5(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -61.00  97.00   0.50   12.50    --   16.22  11.00   8.00  316
  2  \w     20.00  60.00   0.50   12.50    --   16.22-143.00 -38.00   80
  3  \w    -29.00   7.00   0.50   12.50    --  -14.97 -45.00 -90.00   72
  4  \w    -53.00   6.00   0.50   12.50    --   16.22 -45.00 -90.00  118
  5  \w    -85.00 -38.00   0.50   12.50    --  -14.97 -45.00 -90.00   94
  6  \w    -36.00 -10.00   0.50   12.50    --   16.22 -94.00-180.00   52
  7  \w    -90.00 -28.00   0.50   12.50    --  -14.97 159.00 -85.00  124
  8  \w    -36.00 -11.00   0.50   12.50    --  -14.97 125.00 150.00   50
  9  \w    -69.00 -41.00   0.50   12.50    --  -14.97 125.00 150.00   56
 10  \w     11.00  69.00   0.50   12.50    --   16.22-125.00 150.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0053586000
_diffrn_orient_matrix_UB_12      0.0568135000
_diffrn_orient_matrix_UB_13      0.0056160000
_diffrn_orient_matrix_UB_21      0.0199551000
_diffrn_orient_matrix_UB_22      -0.0111650000
_diffrn_orient_matrix_UB_23      0.0269520000
_diffrn_orient_matrix_UB_31      0.1189550000
_diffrn_orient_matrix_UB_32      0.0044203000
_diffrn_orient_matrix_UB_33      -0.0042474000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1186
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10250
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.310
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 528 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0310P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                1866
_reflns_number_total             3183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01527d3.cif
_cod_data_source_block           dbr34
_cod_depositor_comments
'Adding full bibliography for 7160335--7160336.cif.'
_cod_database_code               7160335
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.963
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C5(H5), C13(H13), C22(H22), C16(H16), C2(H2), C3(H3), C14(H14),
 C18(H18), C4(H4), C15(H15), C19(H19), C20(H20), C21(H21)
;
_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 4.581
_oxdiff_exptl_absorpt_empirical_full_min 0.426