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_7122521
_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 rm
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C14 H14 O5'
_chemical_formula_sum            'C14 H14 O5'
_chemical_formula_weight         262.25
_chemical_melting_point          408
_chemical_name_common
' 3,6-Anhydro-2-deoxy-5-O-methyl-7-C-phenyl-D-ido-hept-7-ulosono-1,4-lactone'
_chemical_name_systematic
' 3,6-Anhydro-2-deoxy-5-O-methyl-7-C-phenyl-D-ido-hept-7-ulosono-1,4-lactone'
_space_group_crystal_system      orthorhombic
_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     dual
_atom_sites_solution_secondary   dual
_audit_creation_date             2017-11-29T10:46:25-00:00
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.6740(2)
_cell_length_b                   12.9175(7)
_cell_length_c                   21.3349(7)
_cell_measurement_reflns_used    2488
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.374
_cell_measurement_theta_min      3.148
_cell_volume                     1288.12(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics
; Mercury CSD (Macrae, C.F.,  et al. (2008). J. Appl. Cryst. 41,
 466--470, doi:10.1107/S0021889807067908)
;
_computing_publication_material
; SHELXLE (H\"ubschle, C.B., et al. (2011). J. Appl. Cryst., 44,
 1281--1284, doi:10.1107/S0021889811043202)'
;
_computing_structure_refinement
; SHELXL-2017/1 (Sheldrick, G.M. (2015). Acta Cryst. C71, 3--8
        doi:10.1107/S2053229614024218)
;
_computing_structure_solution
; SHELXT 2014/5 (Sheldrick, G.M. (2015). Acta Cryst. A71, 3--8,
 doi:10.1107/S2053273314026370)
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.328
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0272508
_diffrn_orient_matrix_UB_12      -0.0413423
_diffrn_orient_matrix_UB_13      -0.0210575
_diffrn_orient_matrix_UB_21      -0.046953
_diffrn_orient_matrix_UB_22      0.0359149
_diffrn_orient_matrix_UB_23      -0.0229333
_diffrn_orient_matrix_UB_31      0.1417381
_diffrn_orient_matrix_UB_32      0.0039714
_diffrn_orient_matrix_UB_33      -0.0116469
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9417
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        26.32
_diffrn_reflns_theta_max         29.09
_diffrn_reflns_theta_min         3.154
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
 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
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.177
_exptl_transmission_factor_max   0.982
_exptl_transmission_factor_min   0.964
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.03
_refine_ls_abs_structure_details
; Absolute structure parameter is meaningless because the compound is a weak 
 anomalous scatterer.

 Flack x determined using 703 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 _refine_ls_abs_structure_Flack          0.3(5)
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0454P)^2^+0.1461P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.824
_reflns_number_gt                2246
_reflns_number_total             2988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8md00431e2.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 7122519--7122524.cif.'
_cod_database_code               7122521
_shelx_res_checksum              65924