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_7160336
_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         'C23 H15 F3 N4 S'
_chemical_formula_sum            'C23 H15 F3 N4 S'
_chemical_formula_weight         436.45
_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             2022-07-26
_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                   6.3340(2)
_cell_length_b                   12.0464(5)
_cell_length_c                   26.3054(10)
_cell_measurement_reflns_used    8781
_cell_measurement_temperature    295.3(5)
_cell_measurement_theta_max      26.7140
_cell_measurement_theta_min      2.2860
_cell_volume                     2007.15(13)
_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      295.3(5)
_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 0.952
_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    -24.00  21.00   0.50   18.00    --  -15.60 -94.00   0.00   90
  2  \w    -74.00   1.00   0.50   18.00    --  -15.60 -30.00  90.00  150
  3  \w     24.00  87.00   0.50   18.00    --   16.22-150.00 148.00  126
  4  \w    -86.00  -3.00   0.50   18.00    --  -15.60 -45.00   0.00  166
  5  \w     54.00  85.00   0.50   18.00    --   16.22  45.00 -90.00   62
  6  \w    -95.00  67.00   0.50   18.00    --  -15.60   8.00-125.00  324
  7  \w    -80.00 -18.00   0.50   18.00    --  -15.60 141.00 109.00  124
;
_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      -0.0125828000
_diffrn_orient_matrix_UB_12      0.0098951000
_diffrn_orient_matrix_UB_13      0.0264047000
_diffrn_orient_matrix_UB_21      0.0075020000
_diffrn_orient_matrix_UB_22      0.0579564000
_diffrn_orient_matrix_UB_23      -0.0043599000
_diffrn_orient_matrix_UB_31      -0.1110647000
_diffrn_orient_matrix_UB_32      0.0028466000
_diffrn_orient_matrix_UB_33      -0.0032710000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14138
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.235
_diffrn_reflns_theta_min         2.293
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56637
_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    1.444
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1159 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1100P)^2^+0.5225P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.1950
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.881
_reflns_number_gt                3350
_reflns_number_total             4137
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01527d3.cif
_cod_data_source_block           dbr36
_cod_depositor_comments
'Adding full bibliography for 7160335--7160336.cif.'
_cod_database_code               7160336
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S F'
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.960
_reflns_odcompleteness_completeness 99.83
_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:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C15(H15), C14(H14), C22(H22), C18(H18), C7(H7), C5(H5),
 C8(H8), C6(H6), C20(H20), C21(H21), C19(H19)
;
_shelx_res_checksum              65071
_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 2.602
_oxdiff_exptl_absorpt_empirical_full_min 0.473