Synthesis and Bioactivity of N-glycosylated 3-(2-Oxo-2- arylethylidene)-indolin-2-ones
Kleeblatt, Dennis; Becker, Martin; Ploetz, Michael; Schönherr, Madeleine; Villinger, Alexander; Hein, Martin; Eberle, Jürgen; Kunz, Manfred; Rahman, Qamar; Langer, Peter; RSC Adv.  (2015) –; doi:10.1039/C4RA14301A

data_7219582
_publ_section_title
;
 Synthesis and Bioactivity of N-glycosylated 3-(2-Oxo-2-
 arylethylidene)-indolin-2-ones
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA14301A
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C28 H26 N2 O11'
_chemical_formula_sum            'C28 H26 N2 O11'
_chemical_formula_weight         566.51
_chemical_name_systematic
(E)-3-(2-(4-Nitrophenyl)-2-oxoethylidene)-1-(2,3,4-tri-<i>O</i>-acetyl-\b-L-rhamno-pyranosyl)indolin-2-one
_space_group_IT_number           19
_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
_audit_update_record
;
2014-08-15 deposited with the CCDC.
2015-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6844(3)
_cell_length_b                   16.3169(6)
_cell_length_c                   22.2670(7)
_cell_measurement_reflns_used    6176
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      48.346
_cell_measurement_theta_min      4.993
_cell_volume                     2791.96(17)
_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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31760
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.81
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         8128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                5740
_reflns_number_total             8128
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c4ra14301a2.cif
_cod_data_source_block           is_dkp070
_cod_database_code               7219582