Base-Controlled Regiospecific Mono-Benzylation/Allylation and Diallylation of 4-Aryl-5-indolyl-1,2,4-triazole-3-thione: Thio-Aza Allyl Rearrangement
Salama, Eid E.; Youssef, Mohamed F.; Boraei, Ahmed T. A.; Haukka, Matti; Soliman, Saied M.; Barakat, Assem; Sarhan, Ahmed A. M.; Crystals 13 (2023) 992–; doi:10.3390/cryst13070992

data_1569445
_publ_section_title
;
 Base-Controlled Regiospecific Mono-Benzylation/Allylation and
 Diallylation of 4-Aryl-5-indolyl-1,2,4-triazole-3-thione: Thio-Aza Allyl
 Rearrangement
;
_journal_issue                   7
_journal_name_full               Crystals
_journal_page_first              992
_journal_paper_doi               10.3390/cryst13070992
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C23 H17 Cl N4 S'
_chemical_formula_sum            'C23 H17 Cl N4 S'
_chemical_formula_weight         416.92
_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   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                70.272(3)
_cell_angle_beta                 69.417(3)
_cell_angle_gamma                67.402(4)
_cell_formula_units_Z            4
_cell_length_a                   12.1537(5)
_cell_length_b                   12.8679(5)
_cell_length_c                   15.0994(5)
_cell_measurement_reflns_used    25883
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      76.5540
_cell_measurement_theta_min      3.7920
_cell_volume                     1984.17(14)
_computing_cell_refinement
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
;
_computing_data_collection
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
;
_computing_data_reduction
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
;
_computing_molecular_graphics
'CrystaMaker X (CrystalMaker Software ltd., 2021)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\f scans and \w scans with \k offset'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            53703
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.966
_diffrn_reflns_theta_min         3.216
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.818
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         8329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0296
_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^)+(0.0371P)^2^+0.7393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7433
_reflns_number_total             8329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2264130.cif
_cod_data_source_block           cftb_14
_cod_original_cell_volume        1984.17(15)
_cod_database_code               1569445
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.694
_shelx_estimated_absorpt_t_max   0.827
_shelx_res_checksum              53261
_shelx_hkl_checksum              88234