Vilsmeier reagent, NaHSe and diclofenac acid chloride: one-pot synthesis of a novel selenoindolinone with potent anticancer activity
Ruberte, Ana Carolina; Aydillo, Carlos; Sharma, Arun K.; Sanmartín, Carmen; Plano, Daniel; RSC Advances 10 (2020) 38404–38408; doi:10.1039/D0RA07332F

data_7241417
_publ_section_title
;
 Vilsmeier reagent, NaHSe and diclofenac acid chloride: one-pot synthesis
 of a novel selenoindolinone with potent anticancer activity
;
_journal_issue                   63
_journal_name_full               'RSC Advances'
_journal_page_first              38404
_journal_page_last               38408
_journal_paper_doi               10.1039/D0RA07332F
_journal_volume                  10
_journal_year                    2020
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C16 H11 Cl2 N O Se'
_chemical_formula_sum            'C16 H11 Cl2 N O Se'
_chemical_formula_weight         383.12
_chemical_melting_point          446
_chemical_name_systematic
((E)-1-(2,6-dichlorophenyl)-3-((methylselanyl)methylene)indolin-2-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-10 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.072(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3923(9)
_cell_length_b                   12.7253(14)
_cell_length_c                   14.6560(15)
_cell_measurement_reflns_used    3722
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.238
_cell_measurement_theta_min      2.427
_cell_volume                     1565.2(3)
_computing_cell_refinement       'SAINT V6.36A (BRUKER, 2016)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.36A (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.34
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13375
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.12
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.737
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_correction_T_min  0.717833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS V2.05 (BRUKER, 2001) was used for absorption correction. R(int) was 0.0808 before and 0.0187 after correction. The Ratio of minimum to maximum transmission is 0.7178. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.1981P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                2893
_reflns_number_total             3859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ra07332f2.cif
_cod_data_source_block           aks4s
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7241417
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'