Synthesis of carbohydrate-based naphthoquinones and their substituted phenylhydrazono derivatives as anticancer agents
Campos, Vinicius R.; Santos, Evelyne A. dos; Ferreira, Vitor F.; Montenegro, Raquel C.; de Souza, Maria C. B. V.; Costa-Lotufo, Letícia V.; de Moraes, Manoel O.; Regufe, Anna K. P.; Jordão, Alessandro K.; Pinto, Angelo C.; Resende, Jackson A. L. C.; Cunha, Anna C.; RSC Advances 2 (2012) 11438–; doi:10.1039/c2ra21514d

data_7238714
_publ_section_title
;
 Synthesis of carbohydrate-based naphthoquinones and their substituted
 phenylhydrazono derivatives as anticancer agents
;
_journal_issue                   30
_journal_name_full               'RSC Advances'
_journal_page_first              11438
_journal_paper_doi               10.1039/c2ra21514d
_journal_volume                  2
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C25 H26 Br N3 O5'
_chemical_formula_sum            'C25 H26 Br N3 O5'
_chemical_formula_weight         528.4
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-05-19
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
?

2012-07-02 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8640(2)
_cell_length_b                   15.2666(18)
_cell_length_c                   26.181(2)
_cell_measurement_reflns_used    9799
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.4579
_cell_measurement_theta_min      2.7662
_cell_measurement_wavelength     0.71073
_cell_volume                     2343.8(3)
_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_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 0.998
_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      -0.0035399714
_diffrn_orient_matrix_UB_12      -0.0225053831
_diffrn_orient_matrix_UB_13      0.023680861
_diffrn_orient_matrix_UB_21      -0.0068739217
_diffrn_orient_matrix_UB_22      0.0405905897
_diffrn_orient_matrix_UB_23      0.0130713471
_diffrn_orient_matrix_UB_31      -0.1207865692
_diffrn_orient_matrix_UB_32      -0.0016504163
_diffrn_orient_matrix_UB_33      -0.0014379164
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18215
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    1.796
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.3871
_exptl_crystal_size_mid          0.1393
_exptl_crystal_size_min          0.0734
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.95
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.95
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0314P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0568
_refine_ls_wR_factor_ref         0.0583
_reflns_number_gt                3855
_reflns_number_total             4782
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ra21514d.txt
_cod_data_source_block           nafrib_br_ph
_cod_original_cell_volume        2343.8(4)
_cod_database_code               7238714