Novel asymmetric 3,5-bis(arylidene)piperidin-4-one derivatives: synthesis, crystal structures and cytotoxicity
Yao, Binrong; Li, Ning; Wang, Chunhua; Hou, Guige; Meng, Qingguo; Yan, Ke; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618006605

data_2021124
_publ_section_title
;
 Novel asymmetric 3,5-bis(arylidene)piperidin-4-one derivatives:
 synthesis, crystal structures and cytotoxicity
;
_journal_coeditor_code           OV3110
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618006605
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C27 H23 F N2 O3'
_chemical_formula_moiety         'C27 H23 F N2 O3'
_chemical_formula_sum            'C27 H23 F N2 O3'
_chemical_formula_weight         442.47
_chemical_name_systematic
(5<i>E</i>)-3-{3-[(<i>E</i>)-(2,3-Dihydroxybenzylidene)amino]benzylidene}-5-(2-fluorobenzylidene)-1-methylpiperidin-4-one
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                94.401(6)
_cell_angle_beta                 97.829(6)
_cell_angle_gamma                106.575(6)
_cell_formula_units_Z            2
_cell_length_a                   7.0689(5)
_cell_length_b                   8.2072(5)
_cell_length_c                   20.1397(16)
_cell_measurement_reflns_used    2081
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.1840
_cell_measurement_theta_min      7.5270
_cell_volume                     1101.18(14)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_molecular_graphics
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.22
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type
'Rigaku SuperNova Dual Source diffractometer with an Eos detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7150
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.984
_diffrn_reflns_theta_min         4.465
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2017)
;
_exptl_crystal_colour            'clear light bronze'
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0733P)^2^+0.0127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1488
_reflns_number_gt                2886
_reflns_number_total             4126
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ov3110sup1.cif
_cod_data_source_block           exp_2476
_cod_database_code               2021124
_cod_database_fobs_code          2021124
_shelx_estimated_absorpt_t_min   0.862
_shelx_estimated_absorpt_t_max   0.985
_shelx_hkl_checksum              4969
_shelx_res_checksum              11185