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_7159149
_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         'C16 H11 Cl N4 O2 S'
_chemical_formula_sum            'C16 H11 Cl N4 O2 S'
_chemical_formula_weight         358.80
_chemical_name_systematic
(E)-4-(4-chlorophenyl)-2-(2-nitrobenzylidene)hydrazinyl)thiazole
_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                 106.6960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.3410(2)
_cell_length_b                   7.29160(10)
_cell_length_c                   25.2961(2)
_cell_measurement_reflns_used    15438
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.0420
_cell_measurement_theta_min      2.5130
_cell_volume                     3240.36(6)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_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    -25.00  53.00   0.50    0.74    --   41.33 -47.00  37.00  156
  2  \w     82.00 167.00   0.50    2.96    --   96.67  25.00 -60.00  170
  3  \w    139.00 164.00   0.50    2.96    --   96.67 117.00-150.00   50
  4  \w    116.00 152.00   0.50    2.96    --   96.67 117.00-180.00   72
  5  \w     99.00 125.00   0.50    2.96    --   96.67 117.00-150.00   52
  6  \w     79.00 163.00   0.50    2.96    --   96.67  47.00-174.00  168
  7  \w     99.00 164.00   0.50    2.96    --   96.67 117.00  30.00  130
  8  \w    105.00 170.00   0.50    2.96    --   96.67  96.00 150.00  130
  9  \w    103.00 137.00   0.50    2.96    --   96.67  25.00 120.00   68
 10  \w     45.00  76.00   0.50    2.96    --   96.67 -68.00 150.00   62
 11  \w     58.00  99.00   0.50    2.96    --   96.67 -96.00 150.00   82
 12  \w     41.00 100.00   0.50    0.74    --   41.33-138.00 120.00  118
 13  \w     33.00  59.00   0.50    2.96    --   96.67 -68.00  90.00   52
 14  \w     30.00  57.00   0.50    2.96    --   96.67 -50.00  30.00   54
 15  \w     30.00  55.00   0.50    2.96    --   96.67 -50.00  60.00   50
 16  \w     30.00  57.00   0.50    2.96    --   96.67 -50.00  90.00   54
 17  \w     30.00  56.00   0.50    2.96    --   96.67 -50.00 120.00   52
 18  \w     30.00  57.00   0.50    2.96    --   96.67 -50.00 150.00   54
 19  \w     24.00  53.00   0.50    2.96    --   96.67 -96.00 150.00   58
 20  \w     31.00  57.00   0.50    2.96    --   96.67 -50.00   0.00   52
 21  \w     30.00  55.00   0.50    2.96    --   96.67 -50.00 -30.00   50
 22  \w     32.00  75.00   0.50    2.96    --   96.67 -68.00 -60.00   86
 23  \w     29.00  68.00   0.50    2.96    --   96.67 -59.00 -90.00   78
 24  \w     31.00  68.00   0.50    2.96    --   96.67 -68.00 -90.00   74
 25  \w     30.00  55.00   0.50    2.96    --   96.67 -50.00 -90.00   50
 26  \w     30.00  57.00   0.50    2.96    --   96.67 -50.00 -60.00   54
 27  \w     31.00  56.00   0.50    2.96    --   96.67 -50.00-150.00   50
 28  \w     46.00  72.00   0.50    2.96    --   96.67 -68.00-180.00   52
 29  \w     30.00  55.00   0.50    2.96    --   96.67 -50.00-180.00   50
 30  \w     41.00 100.00   0.50    0.74    --   41.33-138.00-120.00  118
 31  \w    -24.00  35.00   0.50    0.74    --  -41.33  11.00 -60.00  118
 32  \w    -37.00  27.00   0.50    0.74    --  -41.33  32.00 -30.00  128
 33  \w    -47.00 -15.00   0.50    2.96    --  -82.50  42.00 -30.00   64
 34  \w    -47.00 -15.00   0.50    2.96    --  -82.50  42.00   0.00   64
 35  \w    -53.00 -15.00   0.50    2.96    --  -82.50  47.00-174.00   76
 36  \w    -53.00  26.00   0.50    0.74    --  -41.33  47.00-174.00  158
 37  \w     23.00 109.00   0.50    0.74    --   41.33  47.00-174.00  172
 38  \w     21.00 108.00   0.50    0.74    --   41.33  54.00   0.00  174
 39  \w    -26.00  37.00   0.50    0.74    --   41.33 -32.00 -60.00  126
 40  \w    -30.00  28.00   0.50    0.74    --   41.33 -21.00-180.00  116
 41  \w    -26.00  37.00   0.50    0.74    --   41.33 -32.00 -90.00  126
 42  \w    -30.00  28.00   0.50    0.74    --   41.33 -21.00  30.00  116
 43  \w   -109.00 -23.00   0.50    0.74    --  -41.33 -47.00  37.00  172
 44  \w   -150.00 -64.00   0.50    2.96    --  -82.50 -47.00  37.00  172
;
_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      0.0821456000
_diffrn_orient_matrix_UB_12      -0.0451567000
_diffrn_orient_matrix_UB_13      0.0339977000
_diffrn_orient_matrix_UB_21      -0.0106673000
_diffrn_orient_matrix_UB_22      0.1149972000
_diffrn_orient_matrix_UB_23      0.0483364000
_diffrn_orient_matrix_UB_31      -0.0287918000
_diffrn_orient_matrix_UB_32      -0.1713950000
_diffrn_orient_matrix_UB_33      0.0234517000
_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  0.0278
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22215
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.182
_diffrn_reflns_theta_min         2.515
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.445
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78189
_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            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       needle
_exptl_crystal_F_000             1472
_exptl_crystal_preparation       'Crystalised from ethanol'
_exptl_crystal_recrystallization_method No.
_exptl_crystal_size_max          0.002
_exptl_crystal_size_mid          0.002
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.00057(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         5884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0459P)^2^+0.7592P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5119
_reflns_number_total             5884
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02308c2.cif
_cod_data_source_block           ksk-sd33
_cod_depositor_comments
'Adding full bibliography for 7159147--7159149.cif.'
_cod_database_code               7159149
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S Cl'
_chemical_oxdiff_usercomment     @T
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N12(H12), N36(H36), C14(H14), C38(H38), C26(H26), C2(H2), C30(H30), C5(H5),
 C32(H32), C16(H16), C29(H29), C6(H6), C3(H3), C27(H27), C43(H43), C11(H11),
 C19(H19), C40(H40), C42(H42), C41(H41), C18(H18), C17(H17)
;
_shelx_res_checksum              82721
_olex2_exptl_crystal_mounting_method no.
_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 1.401
_oxdiff_exptl_absorpt_empirical_full_min 0.818