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_7122522
_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         'C15 H20 O5'
_chemical_formula_structural     'C15 H20 O5'
_chemical_formula_sum            'C15 H20 O5'
_chemical_formula_weight         280.31
_chemical_melting_point          370
_chemical_name_common
1,2-O-isopropylidene-3-O-methyl-5-C-phenil-\b-L-ido-pentofuranose
_chemical_name_systematic
1,2-O-isopropylidene-3-O-methyl-5-C-phenil-\b-L-ido-pentofuranose
_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   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_audit_creation_date             2014-01-22T19:03:20-00:00
_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                   8.8306(3)
_cell_length_b                   10.0761(3)
_cell_length_c                   17.1204(6)
_cell_measurement_reflns_used    4914
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.317
_cell_measurement_theta_min      3.867
_cell_volume                     1523.34(9)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material
' SHELXLE (H\"ubschle et al., 2011) and WINGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution
; SUPERFLIP (Palatinus L. and Chapuis G., 2007) and
  EDMA (Van Smaalen et al, 2003)
;
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 16.328
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Agilent Technologies)'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_orient_matrix_UB_11      -0.0202388
_diffrn_orient_matrix_UB_12      -0.0670555
_diffrn_orient_matrix_UB_13      -0.0072283
_diffrn_orient_matrix_UB_21      -0.0032605
_diffrn_orient_matrix_UB_22      0.0134201
_diffrn_orient_matrix_UB_23      -0.0406493
_diffrn_orient_matrix_UB_31      0.0776914
_diffrn_orient_matrix_UB_32      -0.0168915
_diffrn_orient_matrix_UB_33      -0.0035662
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13354
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.91
_diffrn_reflns_theta_full        26.32
_diffrn_reflns_theta_max         28.855
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_power             2
_diffrn_source_type              'Enhance (Mo (Agilent Technologies)'
_diffrn_source_voltage           40
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.89974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm using CrysAlisPro 
 (Agilent Technologies,2013).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;

 The absolute structure parameter is essentially meaningless because 
 the compound is a weak anomalous scatterer.

 Flack x determined using 1219 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons et al., 2013).

_refine_ls_abs_structure_Flack          0.4(2)
;
_refine_ls_extinction_coef       0.047(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0391P)^2^+0.1727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                3218
_reflns_number_total             3626
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8md00431e2.cif
_cod_data_source_block           18
_cod_depositor_comments
'Adding full bibliography for 7122519--7122524.cif.'
_cod_database_code               7122522
_shelx_estimated_absorpt_t_min   0.914
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              62127