Alternative and efficient one-pot three-component synthesis of substituted 2-aryl-4-styrylquinazolines/4-styrylquinazolines from synthetically available 1-(2-aminophenyl)-3-arylprop-2-en-1-ones: characterization and evaluation of their antiproliferative activities
Rodríguez, Diego Fernando; Lipez, Kelly Johanna; Stashenko, Elena; Díaz, Iván; Cobo, Justo; Palma, Alirio; RSC Advances 14 (2024) 20951–20965; doi:10.1039/D4RA03702B

data_7248930
_publ_section_title
;
 Alternative and efficient one-pot three-component synthesis of
 substituted 2-aryl-4-styrylquinazolines/4-styrylquinazolines from
 synthetically available 1-(2-aminophenyl)-3-arylprop-2-en-1-ones:
 characterization and evaluation of their antiproliferative activities
;
_journal_issue                   29
_journal_name_full               'RSC Advances'
_journal_page_first              20951
_journal_page_last               20965
_journal_paper_doi               10.1039/D4RA03702B
_journal_volume                  14
_journal_year                    2024
_chemical_compound_source        Synthetic
_chemical_formula_moiety         'C17 H14 N2 O'
_chemical_formula_sum            'C17 H14 N2 O'
_chemical_formula_weight         262.30
_chemical_melting_point          367(1)
_chemical_name_systematic        (E)--4--(4--Methoxystyryl)quinazoline
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-04-19 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.6763(13)
_cell_length_b                   3.9753(2)
_cell_length_c                   13.3702(7)
_cell_measurement_reflns_used    8910
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      3.3
_cell_volume                     1311.56(12)
_computing.cell_refinement       'SAINT V8.40B (Bruker AXS Inc., 2019)'
_computing_data_collection       'APEX4 v2021.10-0 (Bruker Nano Inc., 2021)'
_computing.data_reduction        'SAINT V8.40B (Bruker AXS Inc., 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON-II-CPAD Technology'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24495
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.134
_diffrn_reflns_theta_min         2.246
_diffrn_source
'INCOATEC high brilliance microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.663
_exptl.absorpt_correction_type   Multi--Scan
_exptl.absorpt_process_details
'SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       Block
_exptl_crystal_F_000             552
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane-Ethy acetate mixture (9:1)'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1187 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0304P)^2^+0.3624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2668
_reflns_number_total             2885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra03702b2.cif
_cod_data_source_block           shelx_CCDC1
_cod_database_code               7248930
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.992
_shelx_estimated_absorpt_t_max   0.997
_computing_bruker_data_scaling
'SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction'
_shelx_res_checksum              29362
_shelx_hkl_checksum              75265