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_2244059
_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_coeditor_code           VM2261
_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          'C20 H13 N3 O2 S Se'
_chemical_formula_moiety         'C20 H13 N3 O2 S Se'
_chemical_formula_sum            'C20 H13 N3 O2 S Se'
_chemical_formula_weight         438.35
_chemical_name_systematic
;
5-[1-(Benzenesulfonyl)-1<i>H</i>-indol-3-yl]-2,1,3-benzoselenadiazole
;
_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
_atom_sites_solution_secondary   dual
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90.970(4)
_cell_angle_beta                 92.771(4)
_cell_angle_gamma                94.283(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7760(3)
_cell_length_b                   9.9573(4)
_cell_length_c                   11.4124(6)
_cell_measurement_reflns_used    4183
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      66.7360
_cell_measurement_theta_min      3.8710
_cell_volume                     879.95(7)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0300
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9941
_diffrn_reflns_theta_full        67.189
_diffrn_reflns_theta_max         67.189
_diffrn_reflns_theta_min         3.879
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.183
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_description       Plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.614
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0588P)^2^+0.2071P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                2571
_reflns_number_total             3113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            vm2261sup1.cif
_cod_data_source_block           p-bSe
_cod_database_code               2244059
_shelx_estimated_absorpt_t_min   0.504
_shelx_estimated_absorpt_t_max   0.959
_shelx_hkl_checksum              99249
_shelx_res_checksum              84157
_cod_database_fobs_code 2244059