Synthesis and antiproliferative activity of N-glycosyl-3,3-diaryloxindoles
Kleeblatt, Dennis; Cordes, Christoph A.; Lebrenz, Philipp; Hein, Martin; Feist, Holger; Matin, Abdul; Raza, Rabia; Iqbal, Jamshed; Munshi, Omar; Rahman, Qamar; Villinger, Alexander; Langer, Peter; RSC Advances 4 (2014) 22828–; doi:10.1039/c4ra02627f

data_7235656
_publ_section_title
;
 Synthesis and antiproliferative activity of
 N-glycosyl-3,3-diaryloxindoles
;
_journal_issue                   44
_journal_name_full               'RSC Advances'
_journal_page_first              22828
_journal_paper_doi               10.1039/c4ra02627f
_journal_volume                  4
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C32 H31 N O8'
_chemical_formula_sum            'C32 H31 N O8'
_chemical_formula_weight         557.58
_chemical_name_systematic
1-(2,3,4-Tri-<i>O</i>-acetyl-\b-L-rhamnopyranosyl)-3,3-diphenylindolin-2-one
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8591(2)
_cell_length_b                   14.2792(2)
_cell_length_c                   15.2290(2)
_cell_measurement_reflns_used    8775
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      52.542
_cell_measurement_theta_min      5.033
_cell_volume                     2796.31(7)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32050
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         7963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0474P)^2^+0.0114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0940
_reflns_number_gt                6199
_reflns_number_total             7963
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c4ra02627f2.cif
_cod_data_source_block           is_dkp045
_cod_database_code               7235656