A new biologically active molecular scaffold: crystal structure of 7-(3-hydroxyphenyl)-4-methyl-2<i>H</i>-[1,2,4]triazolo[3,2-<i>c</i>][1,2,4]triazole and selective antiproliferative activity of three isomeric triazolo–triazoles
Fusco, Sandra; Capasso, Domenica; Centore, Roberto; Di Gaetano, Sonia; Parisi, Emmanuele; Acta Crystallographica Section C 75 (2019) 1398–1404; doi:10.1107/S2053229619012403

data_2021772
_publ_section_title
;
 A new biologically active molecular scaffold: crystal structure of
 7-(3-hydroxyphenyl)-4-methyl-2<i>H</i>-[1,2,4]triazolo[3,2-<i>c</i>][1,2,4]triazole
 and selective antiproliferative activity of three isomeric
 triazolo--triazoles
;
_journal_coeditor_code           YP3193
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1398
_journal_page_last               1404
_journal_paper_doi               10.1107/S2053229619012403
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C10 H9 N5 O'
_chemical_formula_moiety         'C10 H9 N5 O'
_chemical_formula_sum            'C10 H9 N5 O'
_chemical_formula_weight         215.22
_chemical_name_systematic
3-(3-Hydroxyphenyl)-6-methyl-1<i>H</i>-[1,2,4]triazolo[3,2-<i>c</i>][1,2,4]triazole
_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'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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                   12.251(5)
_cell_length_b                   7.457(3)
_cell_length_c                   20.863(6)
_cell_measurement_reflns_used    138
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.816
_cell_measurement_theta_min      3.575
_cell_volume                     1906.0(12)
_computing_cell_refinement
;
DIRAX/LSQ (Duisenberg <i>et al.</i>, 2000)
;
_computing_data_collection
;
<i>COLLECT</i> (Nonius, 1999)
;
_computing_data_reduction
;
EvalCCD (Duisenberg <i>et al.</i>, 2003)
;
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 2012) and
Mercury (Macrae <i>et al.</i>, 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR97 (Altomare <i>et al.</i>, 1999)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method
;
CCD rotation images, thick slices
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14282
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.566
_diffrn_reflns_theta_min         3.326
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Bruker, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0463P)^2^+0.6519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1183
_reflns_number_gt                1351
_reflns_number_total             2171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yp3193sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2021772.cif.'
_cod_database_code               2021772
_cod_database_fobs_code          2021772
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.990
_shelx_hkl_checksum              95977
_shelx_res_checksum              98835