Design, synthesis and in-vitro anti-leukemic evaluation of ferulic acid analogues as BCR-Abl inhibitors
R, Narendran; Subramaniam, Shankar; Raja, MR Charan; Venkatasubba Rao, Himesh Makala; R, Subhashree; Ulaganathan, Venkatasubramanian; Pemiah, Brindha; Kar Mahapatra, Santanu; Sivasubramanian, Aravind; RSC Adv.  (2016) –; doi:10.1039/C6RA10106B

data_7225910
_publ_section_title
;
 Design, synthesis and in-vitro anti-leukemic evaluation of ferulic acid
 analogues as BCR-Abl inhibitors
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA10106B
_journal_year                    2016
_chemical_formula_moiety         'C20 H16 O4'
_chemical_formula_sum            'C20 H16 O4'
_chemical_formula_weight         320.33
_chemical_name_systematic
1,2-dihydro-1-(4-hydroxy-3-methoxyphenyl)benzo[f]chromen-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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-01-23 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4475(15)
_cell_length_b                   15.152(4)
_cell_length_c                   16.598(5)
_cell_measurement_reflns_used    8649
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.45
_cell_volume                     1621.5(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.001
_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  0.0243
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13086
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.820
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.093
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
; 
 Flack x determined using 1053 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       0.0159(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0266
_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^)+(0.0254P)^2^+0.2124P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0632
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2636
_reflns_number_total             2852
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra10106b2.cif
_cod_data_source_block           FA1
_cod_original_cell_volume        1621.5(7)
_cod_database_code               7225910
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              34731
_shelx_hkl_checksum              29246