#------------------------------------------------------------------------------
#$Date: 2024-07-05 20:52:10 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293231 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159944.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_7159944
loop_
_publ_author_name
'Djokić, Sanja'
'Benedeković, Goran'
'Kesić, Jelena'
'Rodić, Marko V'
'Popsavin, Mirjana'
'Popsavin, Velimir'
'Francuz, Jovana'
_publ_section_title
;
 First total synthesis of asperilactone B. Revision of absolute
 stereochemistry of asperilactones B and C.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4864
_journal_page_last               4867
_journal_paper_doi               10.1039/d4ob00583j
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_enantioexcess_bulk     1
_chemical_enantioexcess_bulk_technique OA
_chemical_formula_moiety         'C8 H14 O6'
_chemical_formula_sum            'C8 H14 O6'
_chemical_formula_weight         206.19
_chemical_melting_point          365
_chemical_name_common            '(+)-Asperilactone B monohydrate'
_chemical_name_systematic
' 3,6-Anhydro--2,8-dideoxy-D-glycero-D-ido-octono-1,4-lactone monohydrate'
_chemical_optical_rotation       '[\a]^25^~D~ = +43.6 (c = 0.5, Me~2~CO)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-02-19 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.860(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4932(6)
_cell_length_b                   6.85772(19)
_cell_length_c                   8.9304(3)
_cell_measurement_reflns_used    3484
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      71.8450
_cell_measurement_theta_min      5.1290
_cell_volume                     976.30(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'ShelXle (Hübschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  56.00   1.00    5.00    --   36.41 -37.00-150.00   89
  2  ω     17.00 106.00   1.00    5.00    --   36.41  37.00-180.00   89
  3  ω     61.00 109.00   1.00    5.00    --   36.41 178.00-180.00   48
  4  ω    -33.00  56.00   1.00    5.00    --   36.41 -37.00-150.00   89
  5  ω      1.00  74.00   1.00    5.00    --   36.41 -99.00-180.00   73
  6  ω     20.00 104.00   1.00    5.00    --   36.41  57.00-150.00   84
  7  ω     56.00 109.00   1.00    5.00    --   36.41-178.00 120.00   53
  8  ω     20.00 104.00   1.00    5.00    --   36.41  57.00 -60.00   84
  9  ω      1.00  74.00   1.00    5.00    --   36.41 -99.00 -30.00   73
 10  ω     20.00 104.00   1.00    5.00    --   36.41  54.00  -3.00   84
 11  ω     87.00 178.00   1.00   20.00    --  108.00  30.00-180.00   91
 12  ω     39.00  99.00   1.00   20.00    --  108.00 -94.00  30.00   60
 13  ω     41.00 109.00   1.00   20.00    --  108.00-111.00 -60.00   68
 14  ω     39.00  99.00   1.00   20.00    --  108.00 -94.00  30.00   60
 15  ω     70.00 121.00   1.00   20.00    --  108.00 -30.00-120.00   51
 16  ω    104.00 177.00   1.00   20.00    --  108.00   0.00 120.00   73
 17  ω     43.00  85.00   1.00   20.00    --  108.00   0.00 120.00   42
 18  ω     51.00 106.00   1.00   20.00    --  108.00 -94.00 -30.00   55
 19  ω     70.00  96.00   1.00   20.00    --  108.00 -94.00-150.00   26
 20  ω    102.00 152.00   1.00   20.00    --  108.00  77.00-150.00   50
 21  ω    105.00 131.00   1.00   20.00    --  108.00 -77.00  90.00   26
 22  ω     45.00 120.00   1.00   20.00    --  108.00 -45.00-120.00   75
 23  ω     44.00 106.00   1.00   20.00    --  108.00 -94.00 150.00   62
 24  ω     41.00 125.00   1.00   20.00    --  108.00 -45.00   0.00   84
 25  ω     48.00  90.00   1.00   20.00    --  108.00-111.00 150.00   42
 26  ω    109.00 175.00   1.00   20.00    --  108.00  77.00  30.00   66
 27  ω    -17.00   9.00   1.00    5.00    --   36.66 -77.00 -60.00   26
 28  ω     35.00  61.00   1.00    5.00    --   36.66 -99.00  60.00   26
 29  ω      1.00  26.00   1.00    5.00    --   36.66 -99.00  60.00   25
 30  ω    104.00 136.00   1.00   20.00    --  108.00 111.00 150.00   32
 31  ω    119.00 145.00   1.00   20.00    --  108.00 111.00 -60.00   26
 32  ω     67.00 105.00   1.00   20.00    --  108.00 -94.00  60.00   38
 33  ω     81.00 115.00   1.00   20.00    --  108.00 -15.00-180.00   34
 34  ω     20.00 104.00   1.00    5.00    --   36.66  57.00  60.00   84
 35  ω    -33.00  56.00   1.00    5.00    --   36.66 -37.00  60.00   89
 36  ω      0.00  26.00   1.00    5.00    --   36.66  94.00-142.98   26
 37  ω      4.00  35.00   1.00    5.00    --   36.66  87.00 153.67   31
 38  ω      2.00  28.00   1.00    5.00    --   36.66  92.00 -81.52   26
 39  ω      0.00  26.00   1.00    5.00    --   36.66  94.00  81.95   26
 40  ω    -33.00  56.00   1.00    5.00    --   36.66 -37.00 -30.00   89
 41  ω     20.00 104.00   1.00    5.00    --   36.66  57.00 120.00   84
 42  ω      5.00  37.00   1.00    5.00    --   36.66  85.00  18.88   32
 43  ω      7.00 108.00   1.00    5.00    --   36.66  19.00  30.00  101
 44  ω      2.00  28.00   1.00    5.00    --   36.66  92.00  71.18   26
 45  ω     20.00 104.00   1.00    5.00    --   36.66  57.00-120.00   84
 46  ω    -18.00  63.00   1.00    5.00    --   36.66 -77.00-150.00   81
 47  ω     90.00 155.00   1.00   20.00    --  108.00  61.00   0.00   65
 48  ω     70.00 178.00   1.00   20.00    --  108.00  15.00 -30.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0140890000
_diffrn_orient_matrix_UB_12      -0.1841483000
_diffrn_orient_matrix_UB_13      -0.0888289000
_diffrn_orient_matrix_UB_21      -0.0606013000
_diffrn_orient_matrix_UB_22      -0.1145066000
_diffrn_orient_matrix_UB_23      0.0730246000
_diffrn_orient_matrix_UB_31      -0.0739561000
_diffrn_orient_matrix_UB_32      0.0587086000
_diffrn_orient_matrix_UB_33      -0.1364302000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6007
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.059
_diffrn_reflns_theta_min         5.124
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.698
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
; 
 Flack x determined using 747 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.07(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1874
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0502P)²+0.1908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                1769
_reflns_number_total             1874
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00583j3.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7159944--7159948.cif.'
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7159944
_shelx_shelxl_version_number     2019/3
_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. 
;
_shelx_estimated_absorpt_t_min   0.529
_shelx_estimated_absorpt_t_max   0.943
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7085(2) 0.8166(4) 0.3421(3) 0.0940(9) Uani 1 1 d . . . . .
O4 O 0.74785(12) 0.8127(3) 0.5981(2) 0.0594(5) Uani 1 1 d . . . . .
O5 O 0.70607(13) 0.7715(3) 0.9779(2) 0.0591(5) Uani 1 1 d . . . . .
H5A H 0.749(3) 0.796(7) 1.023(3) 0.089 Uiso 1 1 calc R U . . .
O6 O 0.57429(11) 0.8078(3) 0.6943(2) 0.0622(6) Uani 1 1 d . . . . .
O7 O 0.62629(12) 0.3495(3) 0.8919(3) 0.0609(5) Uani 1 1 d . . . . .
H7A H 0.6037(19) 0.279(5) 0.934(5) 0.091 Uiso 1 1 calc R U . . .
C1 C 0.69450(19) 0.8622(4) 0.4624(3) 0.0590(7) Uani 1 1 d . . . . .
C2 C 0.62225(18) 0.9731(4) 0.4903(3) 0.0581(7) Uani 1 1 d . . . . .
H2A H 0.569657 0.919178 0.429733 0.070 Uiso 1 1 calc R U . . .
H2B H 0.625307 1.109106 0.462329 0.070 Uiso 1 1 calc R U . . .
C3 C 0.62888(16) 0.9533(4) 0.6606(3) 0.0495(6) Uani 1 1 d . . . . .
H3 H 0.619975 1.079123 0.705920 0.059 Uiso 1 1 calc R U . . .
C4 C 0.71837(15) 0.8792(4) 0.7289(3) 0.0480(6) Uani 1 1 d . . . . .
H4 H 0.754813 0.979936 0.788835 0.058 Uiso 1 1 calc R U . . .
C5 C 0.70771(15) 0.7064(4) 0.8284(3) 0.0448(5) Uani 1 1 d . . . . .
H5 H 0.750761 0.606665 0.832475 0.054 Uiso 1 1 calc R U . . .
C6 C 0.62071(15) 0.6339(4) 0.7460(3) 0.0436(5) Uani 1 1 d . . . . .
H6 H 0.624513 0.557346 0.655401 0.052 Uiso 1 1 calc R U . . .
C7 C 0.57451(16) 0.5155(4) 0.8409(3) 0.0459(5) Uani 1 1 d . . . . .
H7 H 0.569876 0.591767 0.931129 0.055 Uiso 1 1 calc R U . . .
C8 C 0.48783(19) 0.4551(6) 0.7490(4) 0.0725(9) Uani 1 1 d . . . . .
H8A H 0.453651 0.568963 0.719323 0.109 Uiso 1 1 calc R U . . .
H8B H 0.462878 0.372098 0.811388 0.109 Uiso 1 1 calc R U . . .
H8C H 0.491960 0.385759 0.657800 0.109 Uiso 1 1 calc R U . . .
O8 O 0.58592(16) 0.0266(5) 1.0503(3) 0.0835(8) Uani 1 1 d D . . . .
H81 H 0.538(2) 0.032(15) 0.995(8) 0.125 Uiso 0.5 1 d D U P A 1
H82 H 0.595(6) -0.031(13) 1.138(6) 0.125 Uiso 0.5 1 d D U P B 2
H83 H 0.612(3) -0.047(7) 1.007(5) 0.125 Uiso 1 1 d D U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O4 C4 111.7(2) . . ?
C5 O5 H5A 109.5 . . ?
C3 O6 C6 109.70(17) . . ?
C7 O7 H7A 109.5 . . ?
O1 C1 O4 120.7(3) . . ?
O1 C1 C2 129.1(3) . . ?
O4 C1 C2 110.2(2) . . ?
C1 C2 C3 105.6(2) . . ?
C1 C2 H2A 110.6 . . ?
C3 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
O6 C3 C2 113.0(2) . . ?
O6 C3 C4 106.2(2) . . ?
C2 C3 C4 104.2(2) . . ?
O6 C3 H3 111.0 . . ?
C2 C3 H3 111.0 . . ?
C4 C3 H3 111.0 . . ?
O4 C4 C5 109.8(2) . . ?
O4 C4 C3 105.8(2) . . ?
C5 C4 C3 104.3(2) . . ?
O4 C4 H4 112.1 . . ?
C5 C4 H4 112.1 . . ?
C3 C4 H4 112.1 . . ?
O5 C5 C4 109.9(2) . . ?
O5 C5 C6 108.4(2) . . ?
C4 C5 C6 102.04(19) . . ?
O5 C5 H5 112.0 . . ?
C4 C5 H5 112.0 . . ?
C6 C5 H5 112.0 . . ?
O6 C6 C7 108.90(19) . . ?
O6 C6 C5 104.2(2) . . ?
C7 C6 C5 117.0(2) . . ?
O6 C6 H6 108.8 . . ?
C7 C6 H6 108.8 . . ?
C5 C6 H6 108.8 . . ?
O7 C7 C8 111.1(2) . . ?
O7 C7 C6 105.1(2) . . ?
C8 C7 C6 112.6(2) . . ?
O7 C7 H7 109.3 . . ?
C8 C7 H7 109.3 . . ?
C6 C7 H7 109.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H81 O8 H83 106(4) . . ?
H82 O8 H83 99(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.197(4) . ?
O4 C1 1.346(3) . ?
O4 C4 1.449(3) . ?
O5 C5 1.414(3) . ?
O5 H5A 0.74(5) . ?
O6 C3 1.427(3) . ?
O6 C6 1.428(3) . ?
O7 C7 1.426(3) . ?
O7 H7A 0.77(5) . ?
C1 C2 1.488(5) . ?
C2 C3 1.503(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.532(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.518(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.519(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.513(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.512(4) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O8 H81 0.82(3) . ?
O8 H82 0.86(3) . ?
O8 H83 0.82(2) . ?
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
_geom_hbond_publ_flag
O5 H5A O7 0.74 2.03 2.763(3) 169.1 4_657 yes
O7 H7A O8 0.77 2.08 2.799(4) 157.0 . yes
O8 H81^a O8 0.82(3) 1.98(4) 2.745(5) 155(9) 2_657 yes
O8 H82^b O1 0.86(3) 2.49(7) 3.202(4) 142(8) 1_546 yes
O8 H83 O5 0.82(2) 2.06(3) 2.839(4) 159(5) 1_545 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O4 C1 O1 -179.1(3) . . . . ?
C4 O4 C1 C2 0.9(3) . . . . ?
O1 C1 C2 C3 169.3(3) . . . . ?
O4 C1 C2 C3 -10.6(3) . . . . ?
C6 O6 C3 C2 100.9(2) . . . . ?
C6 O6 C3 C4 -12.7(3) . . . . ?
C1 C2 C3 O6 -99.6(2) . . . . ?
C1 C2 C3 C4 15.3(3) . . . . ?
C1 O4 C4 C5 121.1(2) . . . . ?
C1 O4 C4 C3 9.1(3) . . . . ?
O6 C3 C4 O4 104.7(2) . . . . ?
C2 C3 C4 O4 -14.9(3) . . . . ?
O6 C3 C4 C5 -11.2(3) . . . . ?
C2 C3 C4 C5 -130.8(2) . . . . ?
O4 C4 C5 O5 160.96(19) . . . . ?
C3 C4 C5 O5 -86.0(2) . . . . ?
O4 C4 C5 C6 -84.1(2) . . . . ?
C3 C4 C5 C6 28.9(2) . . . . ?
C3 O6 C6 C7 157.0(2) . . . . ?
C3 O6 C6 C5 31.5(3) . . . . ?
O5 C5 C6 O6 79.1(2) . . . . ?
C4 C5 C6 O6 -36.9(2) . . . . ?
O5 C5 C6 C7 -41.1(3) . . . . ?
C4 C5 C6 C7 -157.1(2) . . . . ?
O6 C6 C7 O7 -178.01(19) . . . . ?
C5 C6 C7 O7 -60.4(3) . . . . ?
O6 C6 C7 C8 60.9(3) . . . . ?
C5 C6 C7 C8 178.5(3) . . . . ?
