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_7159147
_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         'C18 H17 N5 O2 S'
_chemical_formula_sum            'C18 H17 N5 O2 S'
_chemical_formula_weight         367.43
_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             2021-11-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-03-21 deposited with the CCDC.	2023-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.6060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   17.3929(2)
_cell_length_b                   15.73970(10)
_cell_length_c                   21.0528(2)
_cell_measurement_reflns_used    22795
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.1290
_cell_measurement_theta_min      2.7920
_cell_volume                     5320.59(9)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (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 0.998
_diffrn_measured_fraction_theta_max 0.994
_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    -31.00  30.00   0.50    0.50    --  -40.33  25.00 -30.00  122
  2  \w    -43.00  26.00   0.50    0.50    --  -40.33  38.00-120.00  138
  3  \w    -24.00  35.00   0.50    0.50    --  -40.33  12.00-180.00  118
  4  \w    -28.00  68.00   0.50    0.50    --   40.33 -79.00-157.00  192
  5  \w     41.00  99.00   0.50    0.50    --   40.33-138.00-180.00  116
  6  \w     45.00  71.00   0.50    3.00    --   96.67 -68.00-120.00   52
  7  \w     41.00  67.00   0.50    3.00    --   96.67 -59.00-120.00   52
  8  \w     32.00  57.00   0.50    3.00    --   96.67 -50.00-150.00   50
  9  \w     29.00  57.00   0.50    3.00    --   96.67 -59.00-150.00   56
 10  \w     28.00 124.00   0.50    3.00    --   96.67 -79.00-157.00  192
 11  \w     30.00  56.00   0.50    3.00    --   96.67 -50.00 -30.00   52
 12  \w     30.00  55.00   0.50    3.00    --   96.67 -50.00   0.00   50
 13  \w     58.00  83.00   0.50    3.00    --   96.67 -68.00  30.00   50
 14  \w     30.00  67.00   0.50    3.00    --   96.67 -59.00  90.00   74
 15  \w     37.00  63.00   0.50    3.00    --   96.67 -59.00 150.00   52
 16  \w     30.00 108.00   0.50    3.00    --   96.67-117.00  90.00  156
 17  \w     44.00 127.00   0.50    3.00    --   96.67-145.00  90.00  166
 18  \w     30.00  55.00   0.50    3.00    --   96.67 -50.00 -90.00   50
 19  \w     69.00 166.00   0.50    3.00    --   96.67  79.00 -33.00  194
 20  \w    106.00 153.00   0.50    3.00    --   96.67  96.00  30.00   94
 21  \w    105.00 159.00   0.50    3.00    --   96.67 117.00 -60.00  108
 22  \w     99.00 147.00   0.50    3.00    --   96.67 117.00-150.00   96
 23  \w     94.00 162.00   0.50    3.00    --   96.67 145.00 -90.00  136
 24  \w     72.00 136.00   0.50    3.00    --   96.67  77.00 -60.00  128
 25  \w     13.00 109.00   0.50    0.50    --   40.33  79.00 -33.00  192
 26  \w    -24.00  35.00   0.50    0.50    --  -40.33  12.00 120.00  118
 27  \w    -47.00 -22.00   0.50    3.00    --  -82.50  42.00  90.00   50
 28  \w    -45.00 -16.00   0.50    3.00    --  -82.50  42.00   0.00   58
 29  \w    -57.00 -23.00   0.50    3.00    --  -82.50  50.00 -30.00   68
 30  \w    -68.00  29.00   0.50    0.50    --  -40.33  79.00 -33.00  194
 31  \w    -68.00 -42.00   0.50    3.00    --  -82.50  79.00 -33.00   52
 32  \w    -78.00   4.00   0.50    0.50    --  -40.33 104.00 120.00  164
 33  \w   -106.00 -25.00   0.50    0.50    --  -40.33 -38.00  30.00  162
 34  \w   -105.00 -30.00   0.50    3.00    --  -82.50  77.00 150.00  150
 35  \w   -109.00 -13.00   0.50    0.50    --  -40.33 -79.00-157.00  192
;
_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      -0.0945685000
_diffrn_orient_matrix_UB_12      0.0078905000
_diffrn_orient_matrix_UB_13      -0.0189953000
_diffrn_orient_matrix_UB_21      0.0140834000
_diffrn_orient_matrix_UB_22      0.0830173000
_diffrn_orient_matrix_UB_23      0.0417202000
_diffrn_orient_matrix_UB_31      -0.0082721000
_diffrn_orient_matrix_UB_32      0.0512702000
_diffrn_orient_matrix_UB_33      -0.0645999000
_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  0.0285
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36668
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.191
_diffrn_reflns_theta_min         2.752
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.821
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69549
_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_density_diffrn    1.376
_exptl_crystal_F_000             2304
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.00012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     710
_refine_ls_number_reflns         9658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0552P)^2^+0.5917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8194
_reflns_number_total             9658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02308c2.cif
_cod_data_source_block           ksk-sd16
_cod_depositor_comments
;
Adding full bibliography for 7159147--7159149.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C54 H51 N15 O6 S3'
_cod_original_formula_weight         1102.28
_cod_original_formula_moiety         '3(C18 H17 N5 O2 S)'
_cod_original_formula_units_Z            4
_cod_database_code               7159147
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     @T
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 N12(H12), N64(H64), N38(H38), C32(H32), C31(H31), C8(H8), C58(H58), C6(H6),
 C5(H5), C14(H14), C20(H20), C57(H57), C66(H66), C28(H28), C29(H29), C19(H19),
 C40(H40), C55(H55), C54(H54), C72(H72), C2(H2), C60(H60), C34(H34), C16(H16),
 C46(H46), C17(H17), C68(H68), C3(H3), C42(H42), C71(H71), C69(H69), C45(H45),
 C43(H43)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C49(H49A,H49B,H49C), C75(H75A,H75B,
 H75C), C74(H74A,H74B,H74C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              87268
_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 1.582
_oxdiff_exptl_absorpt_empirical_full_min 0.784