Synthesis of Triazole Derivatives of Levoglucosenone As Promising Anticancer Agents: Effective Exploration of the Chemical Space through retro-aza-Michael//aza-Michael Isomerizations.
Tsai, Yi-Hsuan; Borini Etichetti, Carla M.; Di Benedetto, Carolina; Girardini, Javier E.; Martins, Felipe Terra; Spanevello, Rolando A.; Suárez, Alejandra G; Sarotti, Ariel M.; The Journal of organic chemistry 83 (2018) 3516–3528; doi:10.1021/acs.joc.7b03141

data_4035472
_publ_section_title
;
 Synthesis of Triazole Derivatives of Levoglucosenone As Promising
 Anticancer Agents: Effective Exploration of the Chemical Space through
 retro-aza-Michael//aza-Michael Isomerizations.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3516
_journal_page_last               3528
_journal_paper_doi               10.1021/acs.joc.7b03141
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_sum            'C14 H15 N3 O4'
_chemical_formula_weight         289.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 93.525(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2149(17)
_cell_length_b                   5.5203(15)
_cell_length_c                   19.393(5)
_cell_measurement_reflns_used    2.104
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      5770
_cell_measurement_theta_min      25.051
_cell_volume                     664.1(3)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  KappaCCD
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5770
_diffrn_reflns_point_group_measured_fraction_full 0.864
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.051
_diffrn_reflns_theta_min         2.104
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Blessing, R. H. (1995) Acta Cryst., A51, 33-38'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 551 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2078
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+0.0676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.596
_reflns_Friedel_fraction_full    0.727
_reflns_Friedel_fraction_max     0.743
_reflns_number_gt                1728
_reflns_number_total             2078
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03141_si_003.cif
_cod_data_source_block           AT270A
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035472
_shelxl_version_number           2014-3
_shelx_res_checksum              29124
_shelx_hkl_checksum              88096