Visiblelight-induced ternary electron donor-acceptor complex enabled synthesis of 2-(2-hydrazinyl) thiazole derivatives and the assessment of their antioxidant and antidiabetic therapeutic potential.
Dey, Sovan; Das, Arindam; Yadav, Ram Naresh; Boruah, Palash Jyoti; Bakli, Prerana; Baishya, Tania; Sarkar, Koushik; Barman, Anup; Sahu, Ranabir; Maji, Biplab; Paul, Amit Kumar; Hossain, Md Firoj; Organic & biomolecular chemistry 21 (2023) 1771–1779; doi:10.1039/d2ob02308c

data_7159148
_publ_section_title
;
 Visiblelight-induced ternary electron donor-acceptor complex enabled
 synthesis of 2-(2-hydrazinyl) thiazole derivatives and the assessment of
 their antioxidant and antidiabetic therapeutic potential.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1771
_journal_page_last               1779
_journal_paper_doi               10.1039/d2ob02308c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C17 H13 Br2 N3 S'
_chemical_formula_sum            'C17 H13 Br2 N3 S'
_chemical_formula_weight         451.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-21
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-03-21 deposited with the CCDC.	2023-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.5390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.61780(10)
_cell_length_b                   12.12040(10)
_cell_length_c                   14.86240(10)
_cell_measurement_reflns_used    12373
_cell_measurement_temperature    298
_cell_measurement_theta_max      68.0870
_cell_measurement_theta_min      4.6530
_cell_volume                     1708.58(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.982
_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    -37.00  27.00   0.50    0.33    --  -41.33  32.00  60.00  128
  2  \w    -28.00  30.00   0.50    0.33    --  -41.33  21.00 120.00  116
  3  \w    -47.00 -15.00   0.50    2.00    --  -82.50  42.00 120.00   64
  4  \w    -65.00  26.00   0.50    0.33    --  -41.33  65.00 150.00  182
  5  \w    -30.00  28.00   0.50    0.33    --   41.33 -21.00  90.00  116
  6  \w     21.00 108.00   0.50    0.33    --   41.33  54.00   0.00  174
  7  \w    105.00 170.00   0.50    2.00    --   96.67  96.00 -56.00  130
  8  \w    105.00 170.00   0.50    2.00    --   96.67  96.00-120.00  130
  9  \w     99.00 164.00   0.50    2.00    --   96.67 117.00   0.00  130
 10  \w     83.00 164.00   0.50    2.00    --   96.67  33.00 -30.00  162
 11  \w     82.00 167.00   0.50    2.00    --   96.67  25.00  60.00  170
 12  \w     83.00 164.00   0.50    2.00    --   96.67  33.00 150.00  162
 13  \w     78.00 163.00   0.50    2.00    --   96.67  50.00   0.00  170
 14  \w     82.00 167.00   0.50    2.00    --   96.67  25.00-150.00  170
 15  \w     75.00 164.00   0.50    2.00    --   96.67  59.00-150.00  178
 16  \w     73.00 165.00   0.50    2.00    --   96.67  68.00-180.00  184
 17  \w     71.00 170.00   0.50    2.00    --   96.67  17.00 -60.00  198
 18  \w     80.00 163.00   0.50    2.00    --   96.67  42.00  90.00  166
 19  \w     70.00 165.00   0.50    2.00    --   96.67  77.00  90.00  190
 20  \w     28.00 109.00   0.50    0.33    --   41.33  32.00-150.00  162
 21  \w     30.00  57.00   0.50    2.00    --   96.67 -50.00-150.00   54
 22  \w     29.00  68.00   0.50    2.00    --   96.67 -59.00-180.00   78
 23  \w     22.00 106.00   0.50    2.00    --   96.67 -96.00-164.00  168
 24  \w     44.00 127.00   0.50    2.00    --   96.67-145.00 -30.00  166
 25  \w     41.00 100.00   0.50    0.33    --   41.33-138.00  60.00  118
 26  \w     44.00 127.00   0.50    2.00    --   96.67-145.00  30.00  166
 27  \w     29.00  83.00   0.50    2.00    --   96.67 -68.00 -60.00  108
 28  \w     29.00  83.00   0.50    2.00    --   96.67 -68.00  30.00  108
 29  \w     30.00  57.00   0.50    2.00    --   96.67 -50.00  90.00   54
 30  \w     29.00  83.00   0.50    2.00    --   96.67 -68.00  90.00  108
 31  \w     30.00  57.00   0.50    2.00    --   96.67 -50.00 150.00   54
 32  \w     28.00 105.00   0.50    2.00    --   96.67 -77.00 150.00  154
 33  \w     30.00 109.00   0.50    2.00    --   96.67-117.00  30.00  158
 34  \w     29.00  68.00   0.50    2.00    --   96.67 -59.00 -30.00   78
 35  \w     28.00 105.00   0.50    2.00    --   96.67 -77.00  30.00  154
 36  \w     29.00  68.00   0.50    2.00    --   96.67 -59.00  60.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0726682000
_diffrn_orient_matrix_UB_12      -0.1087852000
_diffrn_orient_matrix_UB_13      -0.0346325000
_diffrn_orient_matrix_UB_21      -0.0571443000
_diffrn_orient_matrix_UB_22      0.0552374000
_diffrn_orient_matrix_UB_23      -0.0920813000
_diffrn_orient_matrix_UB_31      0.1335247000
_diffrn_orient_matrix_UB_32      -0.0356548000
_diffrn_orient_matrix_UB_33      -0.0370423000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16387
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.201
_diffrn_reflns_theta_min         4.662
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_preparation       no.
_exptl_crystal_size_max          0.002
_exptl_crystal_size_mid          0.002
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+1.2634P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0863
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2826
_reflns_number_total             3078
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02308c2.cif
_cod_data_source_block           ksksd10066
_cod_depositor_comments
'Adding full bibliography for 7159147--7159149.cif.'
_cod_database_code               7159148
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C N S H'
_chemical_oxdiff_usercomment     @RT
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H006), C12(H00C), C13(H00E), C10(H00F), C3(H00H), C6(H00I), C9(H00J),
 C16(H00L), C7(H00M), C15(H00N)
2.b Idealised Me refined as rotating group:
 C17(H00A,H00B,H00D)
;
_shelx_res_checksum              75654
_olex2_submission_original_sample_id KSK_KC_SD10066
_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 1.801
_oxdiff_exptl_absorpt_empirical_full_min 0.693