2<i>H</i>-Thiazolo[4,5-<i>d</i>][1,2,3]triazole: synthesis, functionalization, and application in scaffold-hopping.
Miyazaki, Ryuya; Takada, Fumito; Kikuchi, Takunari; Oguro, Yuya; Kamata, Makoto; Yukawa, Takafumi; Kato, Kenta; Muto, Kei; Yamaguchi, Junichiro; Chemical science 15 (2024) 15835–15840; doi:10.1039/d4sc03874f

data_1572495
_publ_section_title
;
 2<i>H</i>-Thiazolo[4,5-<i>d</i>][1,2,3]triazole: synthesis,
 functionalization, and application in scaffold-hopping.
;
_journal_issue                   38
_journal_name_full               'Chemical science'
_journal_page_first              15835
_journal_page_last               15840
_journal_paper_doi               10.1039/d4sc03874f
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C19 H23 N5 S'
_chemical_formula_sum            'C19 H23 N5 S'
_chemical_formula_weight         353.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-06-06 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                80.551(3)
_cell_angle_beta                 86.987(3)
_cell_angle_gamma                77.131(2)
_cell_formula_units_Z            2
_cell_length_a                   6.1240(2)
_cell_length_b                   10.0991(3)
_cell_length_c                   14.9338(6)
_cell_measurement_reflns_used    6221
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.1590
_cell_measurement_theta_min      2.9920
_cell_volume                     888.07(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.942
_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    -59.00 -23.00   0.50    1.40    --  -96.00  61.00-180.00   72
  2  \w    -62.00 -33.00   0.50    1.40    --  -96.00  61.00-150.00   58
  3  \w    -50.00 -21.00   0.50    1.40    --  -96.00  45.00-120.00   58
  4  \w    -70.00 -45.00   0.50    1.40    --  -96.00  61.00-120.00   50
  5  \w    -48.00 -22.00   0.50    1.40    --  -96.00  45.00 -90.00   52
  6  \w    -59.00 -24.00   0.50    1.40    --  -96.00  61.00  90.00   70
  7  \w      8.00  34.00   0.50    0.40    --  -42.99  38.00  90.00   52
  8  \w    -41.00 -16.00   0.50    0.40    --  -42.99  38.00  90.00   50
  9  \w    -23.00  13.00   0.50    0.40    --  -42.99  19.00  30.00   72
 10  \w     14.00 116.00   0.50    0.40    --   42.99  77.00-120.00  204
 11  \w    123.00 175.00   0.50    1.40    --  108.01 116.00-127.00  104
 12  \w     69.00  94.00   0.50    0.40    --   42.99 167.00  18.00   50
 13  \w     86.00 111.00   0.50    1.40    --  108.01 167.00  18.00   50
 14  \w     88.00 177.00   0.50    1.40    --  108.01  61.00  60.00  178
 15  \w     36.00  61.00   0.50    1.40    --  108.01 -61.00   0.00   50
 16  \w     38.00  65.00   0.50    1.40    --  108.01 -77.00   0.00   54
 17  \w     34.00  79.00   0.50    1.40    --  108.01 -77.00 -60.00   90
 18  \w     72.00 100.00   0.50    1.40    --  108.01 -77.00   0.00   56
 19  \w     74.00  99.00   0.50    1.40    --  108.01 -77.00 120.00   50
 20  \w     35.00  60.00   0.50    1.40    --  108.01 -77.00 120.00   50
 21  \w     37.00  64.00   0.50    1.40    --  108.01 -95.00 150.00   54
 22  \w     81.00 108.00   0.50    1.40    --  108.01-116.00 143.00   54
 23  \w     28.00  73.00   0.50    0.40    --   42.99-116.00 143.00   90
 24  \w     82.00 107.00   0.50    0.40    --   42.99-167.00  -2.00   50
 25  \w    102.00 141.00   0.50    1.40    --  108.01-167.00  -2.00   78
 26  \w     51.00  85.00   0.50    1.40    --  108.01 -95.00 -90.00   68
 27  \w     63.00 104.00   0.50    1.40    --  108.01 -95.00 -60.00   82
 28  \w     74.00 106.00   0.50    1.40    --  108.01 -98.00  -5.61   64
 29  \w     36.00  63.00   0.50    1.40    --  108.01 -98.00  -5.61   54
 30  \w     77.00 106.00   0.50    1.40    --  108.01 -95.00 150.00   58
 31  \w    -83.00  -7.00   0.50    0.40    --  -42.99 116.00-127.00  152
 32  \w    -58.00 -28.00   0.50    1.40    --  -96.00 116.00-127.00   60
 33  \w    -92.00 -66.00   0.50    0.40    --  -42.99 167.00  18.00   52
 34  \w    -58.00 -25.00   0.50    1.40    --  -96.00 125.00  30.00   66
 35  \w   -177.00 -53.00   0.50    1.40    --  -96.00 -15.00 -30.00  248
 36  \w   -133.00 -75.00   0.50    1.40    --  -96.00 -45.00-150.00  116
 37  \w    -63.00 -21.00   0.50    0.40    --  -42.99 -38.00 120.00   84
 38  \w   -118.00 -70.00   0.50    0.40    --  -42.99 -38.00 120.00   96
 39  \w   -124.00 -99.00   0.50    1.40    --  -96.00-116.00 143.00   50
 40  \w    -80.00 -46.00   0.50    0.40    --  -42.99-167.00  -2.00   68
 41  \w    -71.00 -46.00   0.50    1.40    --  -96.00-167.00  -2.00   50
 42  \w   -103.00 -78.00   0.50    1.40    --  -96.00-167.00  -2.00   50
 43  \w   -135.00-109.00   0.50    1.40    --  -96.00-167.00  -2.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0201721000
_diffrn_orient_matrix_UB_12      -0.0004879000
_diffrn_orient_matrix_UB_13      -0.1023326000
_diffrn_orient_matrix_UB_21      -0.0948990000
_diffrn_orient_matrix_UB_22      0.1564619000
_diffrn_orient_matrix_UB_23      -0.0143285000
_diffrn_orient_matrix_UB_31      0.2391456000
_diffrn_orient_matrix_UB_32      0.0248895000
_diffrn_orient_matrix_UB_33      -0.0161961000
_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  0.0254
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9014
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.486
_diffrn_reflns_theta_min         3.000
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.702
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0475P)^2^+0.3074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0947
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3077
_reflns_number_total             3432
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03874f2.cif
_cod_data_source_block           11N1
_cod_depositor_comments
'Adding full bibliography for 1572494--1572495.cif.'
_cod_database_code               1572495
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.784
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C11(H11), C5(H5)
1.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B),
 C4(H4A,H4B), C7(H7A,H7B), C6(H6A,H6B)
1.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C19(H19), C18(H18), C17(H17)
;
_shelx_res_checksum              74497
_shelx_hkl_checksum              26077
_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 1.313
_oxdiff_exptl_absorpt_empirical_full_min 0.849