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_7122519
_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         'C15 H18 O5'
_chemical_formula_sum            'C15 H18 O5'
_chemical_formula_weight         278.29
_chemical_melting_point          369
_chemical_name_common
3,6-Anhydro-2-deoxy-5,7-di-O-methyl-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone
_chemical_name_systematic
3,6-Anhydro-2-deoxy-5,7-di-O-methyl-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone
_space_group_IT_number           19
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_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     dual
_atom_sites_solution_secondary   dual
_audit_creation_date             2015-10-10T17:21:57-00:00
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_audit_update_record
;
2018-05-15 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
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_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2861(10)
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_cell_length_c                   18.092(2)
_cell_measurement_reflns_used    1137
_cell_measurement_temperature    294(2)
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_cell_volume                     1473.9(3)
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        CrysAlisPro, Agilent Technologies,
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        (compiled Aug 13 2014,18:06:01)
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
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        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, 2014)'
_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 0.999
_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      -0.0413103
_diffrn_orient_matrix_UB_12      -0.0554914
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_diffrn_orient_matrix_UB_31      0.030456
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_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.124
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
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_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4375
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.404
_diffrn_reflns_theta_max         24.404
_diffrn_reflns_theta_min         2.704
_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) (Oxford Diffraction)'
_exptl_absorpt_coefficient_mu    0.094
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;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)

 Analytical numeric absorption correction using a multifaceted crystal
 model based on expressions derived by R.C. Clark & J.S. Reid
 (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897), followed by
 empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
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_exptl_crystal_description       plate
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_exptl_crystal_size_min          0.03
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_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.165
_refine_ls_abs_structure_details
; The absolute structure parameter is meaningless because the compound is a 
 weak anomalous scatterer.

;
_refine_ls_extinction_coef       6.3(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
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_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.1484P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.237
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_reflns_number_gt                1631
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_cod_data_source_file            c8md00431e2.cif
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_cod_depositor_comments
'Adding full bibliography for 7122519--7122524.cif.'
_cod_database_code               7122519
_cell_oxdiff_length_a            8.2802(17)
_cell_oxdiff_length_b            9.8294(11)
_cell_oxdiff_length_c            18.1090(19)
_cell_oxdiff_angle_alpha         89.897(9)
_cell_oxdiff_angle_beta          90.143(12)
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_cell_oxdiff_volume              1473.9(4)
_cell_oxdiff_measurement_reflns_used 1137
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_shelx_res_checksum              63772