Synthesis of a new class of naphthoquinone glycoconjugates and evaluation of their potential as antitumoral agents
Campos, Vinicius R.; Cunha, Anna C.; Silva, Wanderson A.; Ferreira, Vitor F.; Santos de Sousa, Carla; Fernandes, Patrícia D.; Moreira, Vinícius N.; da Rocha, David R.; Dias, Flaviana R. F.; Montenegro, Raquel C.; de Souza, Maria C. B. V.; Boechat, Fernanda da C. S.; Franco, Caroline F. J.; Resende, Jackson A. L. C.; RSC Adv. 5 (2015) 96222–; doi:10.1039/C5RA19192K

data_7223207
_publ_section_title
;
 Synthesis of a new class of naphthoquinone glycoconjugates and evaluation
 of their potential as antitumoral agents
;
_journal_issue                   116
_journal_name_full               'RSC Adv.'
_journal_page_first              96222
_journal_paper_doi               10.1039/C5RA19192K
_journal_volume                  5
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H19 N3 O7'
_chemical_formula_sum            'C19 H19 N3 O7'
_chemical_formula_weight         401.37
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-09-26T23:33:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-09-22 deposited with the CCDC.
2015-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.139(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9539(2)
_cell_length_b                   5.7856(2)
_cell_length_c                   25.9610(11)
_cell_measurement_reflns_used    3508
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.4111
_cell_measurement_theta_min      2.3493
_cell_measurement_wavelength     0.71073
_cell_volume                     894.10(6)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0590431
_diffrn_orient_matrix_UB_12      -0.1046955
_diffrn_orient_matrix_UB_13      0.0041237
_diffrn_orient_matrix_UB_21      0.0000415
_diffrn_orient_matrix_UB_22      0.0226038
_diffrn_orient_matrix_UB_23      0.0268524
_diffrn_orient_matrix_UB_31      -0.103506
_diffrn_orient_matrix_UB_32      0.0596455
_diffrn_orient_matrix_UB_33      -0.0029357
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            7869
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.354
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.81004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.4354
_exptl_crystal_size_mid          0.1852
_exptl_crystal_size_min          0.0663
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -1.4(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3770
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0332P)^2^+0.2640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                3232
_reflns_number_total             3770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra19192k2.cif
_cod_data_source_block           triazorib
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7223207