Novel <i>O</i>-methyl goniofufurone and 7-<i>epi</i>-goniofufurone derivatives: synthesis, <i>in vitro</i> cytotoxicity and SAR analysis.
Francuz, Jovana; Popsavin, Mirjana; Djokić, Sanja; Kojić, Vesna; Srdić-Rajić, Tatjana; Rodić, Marko V; Jakimov, Dimitar; Popsavin, Velimir; MedChemComm 9 (2018) 2017–2027; doi:10.1039/c8md00431e

data_7122523
_publ_section_title
;
 Novel <i>O</i>-methyl goniofufurone and 7-<i>epi</i>-goniofufurone
 derivatives: synthesis, <i>in vitro</i> cytotoxicity and SAR analysis.
;
_journal_issue                   12
_journal_name_full               MedChemComm
_journal_page_first              2017
_journal_page_last               2027
_journal_paper_doi               10.1039/c8md00431e
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C14 H16 O5'
_chemical_formula_sum            'C14 H16 O5'
_chemical_formula_weight         264.27
_chemical_melting_point          396
_chemical_name_common
' 3,6-Anhydro-2-deoxy-7-O-methyl-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone'
_chemical_name_systematic
' 3,6-Anhydro-2-deoxy-7-O-methyl-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone'
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_creation_date             2015-10-06T20:44:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-05-15 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.533(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6832(2)
_cell_length_b                   7.5202(3)
_cell_length_c                   11.6492(4)
_cell_measurement_reflns_used    6582
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.938
_cell_measurement_theta_min      3.51
_cell_volume                     672.84(4)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Mercury CSD (Macrae et al., 2008)'
_computing_publication_material  'SHELXLE (H\"ubschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 16.328
_diffrn_detector_type            'Sapphire3 (Oxford Diffraction)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_orient_matrix_UB_11      0.0883379
_diffrn_orient_matrix_UB_12      -0.0077473
_diffrn_orient_matrix_UB_13      -0.015533
_diffrn_orient_matrix_UB_21      -0.0142959
_diffrn_orient_matrix_UB_22      -0.0902266
_diffrn_orient_matrix_UB_23      -0.0152998
_diffrn_orient_matrix_UB_31      -0.0228795
_diffrn_orient_matrix_UB_32      0.0263993
_diffrn_orient_matrix_UB_33      -0.0568577
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14574
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        26.32
_diffrn_reflns_theta_max         28.946
_diffrn_reflns_theta_min         2.652
_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) (Oxford Diffraction)'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.93743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details
; Absolute structure parameter is meaningless because the compound is a 
 weak anomalous scatterer.

_refine_ls_abs_structure_details

 Flack x determined using 1250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

_refine_ls_abs_structure_Flack          -0.4(2)
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3236
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0506P)^2^+0.0972P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.098
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                3035
_reflns_number_total             3236
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8md00431e2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7122519--7122524.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7122523
_cell_oxdiff_length_a            7.6819(3)
_cell_oxdiff_length_b            7.5195(3)
_cell_oxdiff_length_c            11.6520(5)
_cell_oxdiff_angle_alpha         89.998(3)
_cell_oxdiff_angle_beta          91.502(3)
_cell_oxdiff_angle_gamma         90.010(3)
_cell_oxdiff_volume              672.83(4)
_cell_oxdiff_measurement_reflns_used 6582
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.973
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              5395