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_7223206
_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_formula_moiety         'C19 H21 N O7'
_chemical_formula_sum            'C19 H21 N O7'
_chemical_formula_weight         375.37
_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   mixed
_audit_creation_date             2014-09-26T23:37:20-00:00
_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                 94.745(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8376(2)
_cell_length_b                   11.9174(4)
_cell_length_c                   12.2331(5)
_cell_measurement_reflns_used    4737
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.357
_cell_measurement_theta_min      1.7053
_cell_volume                     848.13(5)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0622974
_diffrn_orient_matrix_UB_12      0.011593
_diffrn_orient_matrix_UB_13      0.0510193
_diffrn_orient_matrix_UB_21      0.1035744
_diffrn_orient_matrix_UB_22      0.0020821
_diffrn_orient_matrix_UB_23      -0.0264411
_diffrn_orient_matrix_UB_31      -0.0161436
_diffrn_orient_matrix_UB_32      0.0583218
_diffrn_orient_matrix_UB_33      -0.0091794
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9555
_diffrn_reflns_point_group_measured_fraction_full 0.99
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.91783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.47
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.4245
_exptl_crystal_size_mid          0.3329
_exptl_crystal_size_min          0.2135
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3667
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.045
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0437P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.075
_refine_ls_wR_factor_ref         0.0776
_reflns_number_gt                3075
_reflns_number_total             3667
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra19192k2.cif
_cod_data_source_block           aminjuglona
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7223206