Structural study of bioisosteric derivatives of 5-(1<i>H</i>-indol-3-yl)-benzotriazole and their ability to form chalcogen bonds
Mirgaux, Manon; Scaillet, Tanguy; Kozlova, Arina; Tumanov, Nikolay; Frederick, Raphaël; Bodart, Laurie; Wouters, Johan; Acta Crystallographica Section E 78 (2022) –; doi:10.1107/S2056989022002948

data_2244061
_publ_section_title
;
 Structural study of bioisosteric derivatives of
 5-(1<i>H</i>-indol-3-yl)-benzotriazole and their ability to form
 chalcogen bonds
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022002948
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C14 H9 N3 O'
_chemical_formula_moiety         'C14 H9 N3 O'
_chemical_formula_sum            'C14 H9 N3 O'
_chemical_formula_weight         235.24
_chemical_name_systematic
;
5-(1<i>H</i>-Indol-3-yl)-2,1,3-benzoxadiazole
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0256(7)
_cell_length_b                   7.7396(5)
_cell_length_c                   23.8551(16)
_cell_measurement_reflns_used    1395
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      66.3080
_cell_measurement_theta_min      7.4170
_cell_volume                     2220.3(2)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2020)
;
_computing_structure_refinement
;
<i>SHELXL2016/6</i> (Sheldrick, 2015b), <i>ShelXle</i>
(H\"ubschle <i>et al.</i>, 2011), <i>OLEX2</i>
(Dolomanov <i>et al.</i>, 2009)
;
_computing_structure_solution
;
<i>SHELXT2014/5</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6883
_diffrn_reflns_theta_full        67.091
_diffrn_reflns_theta_max         67.091
_diffrn_reflns_theta_min         3.706
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour            'Clear yellow'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       Plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.0873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1337
_reflns_number_gt                1275
_reflns_number_total             1972
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            vm2261sup1.cif
_cod_data_source_block           bO
_cod_database_code               2244061
_shelx_estimated_absorpt_t_min   0.915
_shelx_estimated_absorpt_t_max   0.978
_shelx_hkl_checksum              79552
_shelx_res_checksum              78009
_cod_database_fobs_code 2244061