#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/25/7122523.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7122523
loop_
_publ_author_name
'Francuz, Jovana'
'Popsavin, Mirjana'
'Djokić, Sanja'
'Kojić, Vesna'
'Srdić-Rajić, Tatjana'
'Rodić, Marko V'
'Jakimov, Dimitar'
'Popsavin, Velimir'
_publ_section_title
;
 Novel O-methyl goniofufurone and 7-epi-goniofufurone
 derivatives: synthesis, in vitro 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 (Hübschle 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       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       'ω 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/[σ²(Fo²)+(0.0506P)²+0.0972P] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
        They are only intended as comments.
;
_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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.64604(19) 0.7000(3) 0.99983(17) 0.0656(5) Uani 1 1 d . .
O3 O 0.2617(2) 0.6669(2) 0.74251(13) 0.0515(4) Uani 1 1 d . .
O4 O 0.35974(16) 0.7184(2) 1.00176(12) 0.0436(4) Uani 1 1 d . .
O5 O -0.06760(18) 0.6936(3) 0.85931(16) 0.0609(5) Uani 1 1 d D .
H5A H -0.138(3) 0.690(5) 0.912(2) 0.073 Uiso 1 1 d D U
O7 O 0.0161(2) 0.2728(2) 0.80605(14) 0.0548(5) Uani 1 1 d . .
C1 C 0.5128(2) 0.7472(3) 0.95239(18) 0.0426(5) Uani 1 1 d . .
C2 C 0.4864(3) 0.8428(4) 0.8406(2) 0.0483(5) Uani 1 1 d . .
H2A H 0.5565 0.7902 0.7815 0.058 Uiso 1 1 calc R U
H2B H 0.5165 0.9675 0.8483 0.058 Uiso 1 1 calc R U
C3 C 0.2939(3) 0.8201(3) 0.81250(19) 0.0429(4) Uani 1 1 d . .
H3 H 0.2434 0.9277 0.7778 0.052 Uiso 1 1 calc R U
C4 C 0.2150(2) 0.7792(3) 0.92888(18) 0.0404(5) Uani 1 1 d . .
H4 H 0.1553 0.8821 0.9612 0.049 Uiso 1 1 calc R U
C5 C 0.0923(2) 0.6246(3) 0.90419(16) 0.0388(4) Uani 1 1 d . .
H5 H 0.0763 0.5494 0.9718 0.047 Uiso 1 1 calc R U
C6 C 0.1892(2) 0.5288(3) 0.81021(17) 0.0354(4) Uani 1 1 d . .
H6 H 0.2841 0.459 0.8455 0.042 Uiso 1 1 calc R U
C7 C 0.0808(3) 0.4087(3) 0.73193(17) 0.0400(4) Uani 1 1 d . .
H7 H -0.0176 0.4766 0.6993 0.048 Uiso 1 1 calc R U
C8 C -0.1219(4) 0.1752(5) 0.7555(3) 0.0771(10) Uani 1 1 d . .
H8A H -0.1602 0.0866 0.8085 0.116 Uiso 1 1 calc R U
H8B H -0.083 0.1184 0.6869 0.116 Uiso 1 1 calc R U
H8C H -0.2166 0.254 0.7364 0.116 Uiso 1 1 calc R U
C9 C 0.1839(3) 0.3298(3) 0.63529(17) 0.0400(4) Uani 1 1 d . .
C10 C 0.3382(3) 0.2394(3) 0.6576(2) 0.0527(5) Uani 1 1 d . .
H10 H 0.3824 0.2324 0.7326 0.063 Uiso 1 1 calc R U
C11 C 0.4272(4) 0.1596(4) 0.5701(3) 0.0687(7) Uani 1 1 d . .
H11 H 0.5303 0.0989 0.5867 0.082 Uiso 1 1 calc R U
C12 C 0.3646(4) 0.1693(4) 0.4587(3) 0.0701(8) Uani 1 1 d . .
H12 H 0.4244 0.1144 0.4 0.084 Uiso 1 1 calc R U
C13 C 0.2143(4) 0.2597(4) 0.4346(2) 0.0666(8) Uani 1 1 d . .
H13 H 0.1725 0.2674 0.3591 0.08 Uiso 1 1 calc R U
C14 C 0.1227(3) 0.3407(4) 0.5221(2) 0.0531(5) Uani 1 1 d . .
H14 H 0.0204 0.4022 0.5047 0.064 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 O3 C3 109.62(15)
C1 O4 C4 111.36(17)
C5 O5 H5A 107(2)
C8 O7 C7 112.88(19)
O1 C1 O4 120.0(2)
O1 C1 C2 129.4(2)
O4 C1 C2 110.58(18)
C1 C2 C3 104.03(17)
C1 C2 H2A 110.9
C3 C2 H2A 110.9
C1 C2 H2B 110.9
C3 C2 H2B 110.9
H2A C2 H2B 109
O3 C3 C2 111.5(2)
O3 C3 C4 106.09(16)
C2 C3 C4 103.78(17)
O3 C3 H3 111.7
C2 C3 H3 111.7
C4 C3 H3 111.7
O4 C4 C5 109.30(18)
O4 C4 C3 105.40(15)
C5 C4 C3 104.13(17)
O4 C4 H4 112.5
C5 C4 H4 112.5
C3 C4 H4 112.5
O5 C5 C4 108.45(19)
O5 C5 C6 110.05(16)
C4 C5 C6 100.71(15)
O5 C5 H5 112.3
C4 C5 H5 112.3
C6 C5 H5 112.3
O3 C6 C7 108.51(15)
O3 C6 C5 104.98(16)
C7 C6 C5 116.32(16)
O3 C6 H6 108.9
C7 C6 H6 108.9
C5 C6 H6 108.9
O7 C7 C9 111.35(18)
O7 C7 C6 104.80(15)
C9 C7 C6 112.97(16)
O7 C7 H7 109.2
C9 C7 H7 109.2
C6 C7 H7 109.2
O7 C8 H8A 109.5
O7 C8 H8B 109.5
H8A C8 H8B 109.5
O7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C14 118.2(2)
C10 C9 C7 121.01(18)
C14 C9 C7 120.7(2)
C11 C10 C9 120.9(2)
C11 C10 H10 119.5
C9 C10 H10 119.5
C12 C11 C10 120.4(3)
C12 C11 H11 119.8
C10 C11 H11 119.8
C13 C12 C11 119.6(3)
C13 C12 H12 120.2
C11 C12 H12 120.2
C12 C13 C14 120.6(2)
C12 C13 H13 119.7
C14 C13 H13 119.7
C9 C14 C13 120.2(2)
C9 C14 H14 119.9
C13 C14 H14 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.204(3)
O3 C6 1.427(2)
O3 C3 1.429(3)
O4 C1 1.340(2)
O4 C4 1.454(2)
O5 C5 1.421(2)
O5 H5A 0.83(2)
O7 C8 1.406(3)
O7 C7 1.435(3)
C1 C2 1.496(3)
C2 C3 1.516(3)
C2 H2A 0.97
C2 H2B 0.97
C3 C4 1.531(3)
C3 H3 0.98
C4 C5 1.520(3)
C4 H4 0.98
C5 C6 1.522(3)
C5 H5 0.98
C6 C7 1.516(3)
C6 H6 0.98
C7 C9 1.515(3)
C7 H7 0.98
C8 H8A 0.96
C8 H8B 0.96
C8 H8C 0.96
C9 C10 1.385(3)
C9 C14 1.391(3)
C10 C11 1.379(4)
C10 H10 0.93
C11 C12 1.374(5)
C11 H11 0.93
C12 C13 1.362(5)
C12 H12 0.93
C13 C14 1.394(4)
C13 H13 0.93
C14 H14 0.93
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5A O1 0.83(2) 1.98(2) 2.778(2) 163(3) 1_455
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 O4 C1 O1 -177.9(2)
C4 O4 C1 C2 3.3(2)
O1 C1 C2 C3 165.2(3)
O4 C1 C2 C3 -16.1(3)
C6 O3 C3 C2 105.4(2)
C6 O3 C3 C4 -7.0(2)
C1 C2 C3 O3 -92.4(2)
C1 C2 C3 C4 21.4(2)
C1 O4 C4 C5 122.26(18)
C1 O4 C4 C3 10.9(2)
O3 C3 C4 O4 97.70(19)
C2 C3 C4 O4 -20.0(2)
O3 C3 C4 C5 -17.3(2)
C2 C3 C4 C5 -134.97(19)
O4 C4 C5 O5 165.10(15)
C3 C4 C5 O5 -82.66(18)
O4 C4 C5 C6 -79.37(18)
C3 C4 C5 C6 32.9(2)
C3 O3 C6 C7 153.63(17)
C3 O3 C6 C5 28.6(2)
O5 C5 C6 O3 76.5(2)
C4 C5 C6 O3 -37.8(2)
O5 C5 C6 C7 -43.4(2)
C4 C5 C6 C7 -157.71(17)
C8 O7 C7 C9 -72.8(3)
C8 O7 C7 C6 164.8(2)
O3 C6 C7 O7 178.92(17)
C5 C6 C7 O7 -63.1(2)
O3 C6 C7 C9 57.5(2)
C5 C6 C7 C9 175.53(18)
O7 C7 C9 C10 -64.7(3)
C6 C7 C9 C10 53.0(3)
O7 C7 C9 C14 113.0(2)
C6 C7 C9 C14 -129.4(2)
C14 C9 C10 C11 -1.1(4)
C7 C9 C10 C11 176.6(2)
C9 C10 C11 C12 0.3(5)
C10 C11 C12 C13 0.6(5)
C11 C12 C13 C14 -0.7(4)
C10 C9 C14 C13 1.0(4)
C7 C9 C14 C13 -176.7(2)
C12 C13 C14 C9 -0.1(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189252
