Alternative mechanisms of action for the apoptotic activity of terpenoid-like chalcone derivatives
Custodio, Jean M. F.; Vaz, Wesley F.; Bernardes, Aline; Moura, Andrea F.; Oliver, Allen G.; Molnár, Szilárd; Perjési, Pál; Noda-Perez, Caridad; New Journal of Chemistry 45 (2021) 15267–15279; doi:10.1039/D1NJ02086B

data_7060808
_publ_section_title
;
 Alternative mechanisms of action for the apoptotic activity of
 terpenoid-like chalcone derivatives
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15267
_journal_page_last               15279
_journal_paper_doi               10.1039/D1NJ02086B
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         '2(C10 H11.5 F0.5 O0.5)'
_chemical_formula_sum            'C20 H23 F O'
_chemical_formula_weight         298.38
_chemical_name_systematic
1E,4E-1-(4-fluorophenyl)-5-(2,6,6-trimethylcyclohexen-1-yl)penta-1,4-dien-3-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-18
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2021-04-28 deposited with the CCDC.	2021-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.691(3)
_cell_length_b                   14.305(3)
_cell_length_c                   10.6099(14)
_cell_measurement_reflns_used    7603
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.82
_cell_measurement_theta_min      2.36
_cell_volume                     3292.1(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            70248
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         1.705
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6953
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0616 before and 0.0532 after correction.
The Ratio of minimum to maximum transmission is 0.9324.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       plaque
_exptl_crystal_F_000             1280
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(12)
_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     441
_refine_ls_number_reflns         7256
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0473P)^2^+0.2336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5127
_reflns_number_total             7256
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj02086b2.cif
_cod_data_source_block           brf4
_cod_depositor_comments          'Adding full bibliography for 7060808.cif.'
_cod_original_cell_volume        3292.3(9)
_cod_database_code               7060808
_shelx_shelxl_version_number     2018/1
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9(12)
 0.1(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
C1A \\sim C15B \\sim C14 \\sim C15 \\sim C14A \\sim C1B \\sim C14B \\sim C15A:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
4. Others
 Sof(H16G)=Sof(H16H)=Sof(H16C)=Sof(H16D)=Sof(C14B)=Sof(H14A)=Sof(H14B)=
 Sof(C15B)=Sof(H15C)=Sof(H15D)=Sof(C15)=Sof(H15E)=Sof(H15F)=Sof(C1B)=Sof(H1BA)=
 Sof(H1BB)=1-FVAR(1)
 Sof(H16E)=Sof(H16F)=Sof(H16A)=Sof(H16B)=Sof(C15A)=Sof(H15A)=Sof(H15B)=
 Sof(C14)=Sof(H14E)=Sof(H14F)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C1A)=Sof(H1AA)=
 Sof(H1AB)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C16*(H16G,H16H), C16*(H16E,H16F), C16(H16C,H16D), C16(H16A,H16B), C14B(H14A,
 H14B), C15A(H15A,H15B), C15B(H15C,H15D), C14(H14E,H14F), C15(H15E,H15F),
 C14A(H14C,H14D), C1A(H1AA,H1AB), C1B(H1BA,H1BB)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5*(H5*), C11(H11), C10(H10), C7*(H7*), C8*(H8*), C5(H5), C11*(H11*),
 C8(H8), C1(H1), C10*(H10*), C4*(H4*), C4(H4), C2(H2), C1*(H1*), C2*(H2*)
5.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18*(H18D,H18E,H18F), C20*(H20D,H20E,H20F), C20(H20A,
 H20B,H20C), C19*(H19D,H19E,H19F), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              62037
_olex2_submission_special_instructions 'No special instructions were received'