Synthesis of 6H-indolo[2,3-b]quinoxaline-N-glycosides and their cytotoxic activity against human ceratinocytes (HaCaT)
Driller, Katrin Marie; Libnow, Stefanie; Hein, Martin; Harms, Manuela; Wende, Kristian; Lalk, Michael; Michalik, Dirk; Reinke, Helmut; Langer, Peter; Organic & Biomolecular Chemistry 6 (2008) 4218–4223; doi:10.1039/b812308j

data_7151024
_publ_section_title
;
 Synthesis of 6H-indolo[2,3-b]quinoxaline-N-glycosides and their
 cytotoxic activity against human ceratinocytes (HaCaT)
;
_journal_issue                   22
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              4218
_journal_page_last               4223
_journal_paper_doi               10.1039/b812308j
_journal_volume                  6
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C30 H31 N3 O9'
_chemical_formula_sum            'C30 H31 N3 O9'
_chemical_formula_weight         577.58
_chemical_melting_point          543
_chemical_name_systematic
;
2,3-Dimethyl-6-(2',3',4',6'-tetra-O-acetyl-\b-D-manno-
pyranosyl)indolo[2,3-b]quinoxaline
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                   6.48000(10)
_cell_length_b                   10.5889(2)
_cell_length_c                   41.9162(9)
_cell_measurement_reflns_used    6984
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.78
_cell_measurement_theta_min      2.15
_cell_volume                     2876.12(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_number            41892
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9784
_exptl_absorpt_correction_T_min  0.9255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         4779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0644P)^2^+0.8614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                4318
_reflns_number_total             4779
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812308j.txt
_cod_data_source_block           kd39_(beta3g)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               7151024