Regioselective Suzuki–Miyaura reactions of 4,7-dichloro-N-methylisatin. Synthesis, anti-HIV activity and modeling study
Hamdy, Aws M.; Al-Masoudi, Najim A.; Pannecouque, Christophe; Rahman, Qamar; Villinger, Alexander; Langer, Peter; RSC Adv. 5 (2015) 107360–; doi:10.1039/C5RA16841D

data_7223539
_publ_section_title
;
 Regioselective Suzuki--Miyaura reactions of 4,7-dichloro-N-methylisatin.
 Synthesis, anti-HIV activity and modeling study
;
_journal_issue                   130
_journal_name_full               'RSC Adv.'
_journal_page_first              107360
_journal_paper_doi               10.1039/C5RA16841D
_journal_volume                  5
_journal_year                    2015
_chemical_formula_moiety         'C16 H12 Cl N O2'
_chemical_formula_sum            'C16 H12 Cl N O2'
_chemical_formula_weight         285.72
_chemical_name_systematic
;
7-chloro-1-methyl-4-(4-tolyl)indoline-2,3-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-07-02 deposited with the CCDC.
2015-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.733(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8951(6)
_cell_length_b                   24.185(3)
_cell_length_c                   13.5874(17)
_cell_measurement_reflns_used    381
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      17.93
_cell_measurement_theta_min      2.94
_cell_volume                     1277.3(3)
_computing_cell_refinement       'Bruker Apex v7.51a'
_computing_data_collection       'Bruker Apex v7.51a'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1668
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2893
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.7563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TWINABS; Sheldrick, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.99
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1686
_refine_ls_R_factor_gt           0.0684
_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^)+(0.0439P)^2^+0.6173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                1539
_reflns_number_total             2894
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c5ra16841d2.cif
_cod_data_source_block           is_ac8
_cod_original_cell_volume        1277.2(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7223539