# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 2333775'
loop_
_audit_author_name
_audit_author_address
'Marko Rodic'
;University of Novi Sad
Serbia
;
_audit_update_record             
;
2024-02-19 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
#exp_code: data_SD68-160_2640_2C_a 

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
; 3,6-Anhydro--2,8-dideoxy-D-glycero-D-ido-octono-1,4-lactone monohydrate
;
_chemical_name_common            '(+)-Asperilactone B monohydrate'
_chemical_melting_point          365
_chemical_formula_moiety         'C8 H14 O6'
_chemical_formula_sum            'C8 H14 O6'
_chemical_formula_weight         206.19
_chemical_absolute_configuration rmad
_chemical_enantioexcess_bulk     1
_chemical_enantioexcess_bulk_technique OA
_chemical_optical_rotation       '[\a]^25^~D~ = +43.6 (c = 0.5, Me~2~CO)'

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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. 
;

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'

_cell_length_a                   16.4932(6)
_cell_length_b                   6.85772(19)
_cell_length_c                   8.9304(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.860(3)
_cell_angle_gamma                90
_cell_volume                     976.30(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3484
_cell_measurement_theta_min      5.1290
_cell_measurement_theta_max      71.8450

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.698
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    1.046
_shelx_estimated_absorpt_T_min   0.529
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72350
_exptl_absorpt_correction_T_max  1.00000
_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
;
_diffrn_ambient_temperature      295(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       'ω scans'
_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_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_reflns_number            6007
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.124
_diffrn_reflns_theta_max         72.059
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1874
_reflns_number_gt                1769
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.993

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'ShelXle (Hübschle et al., 2011)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+0.1908P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   .
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_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_number_reflns         1874
_refine_ls_number_parameters     141
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.118
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.029

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ent-I
_database_code_depnum_ccdc_archive 'CCDC 2333776'
loop_
_audit_author_name
_audit_author_address
'Marko Rodic'
;University of Novi Sad
Serbia
;
_audit_update_record             
;
2024-02-19 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
#exp_code: data_SD45-129_2462_mC_2_a  

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
; 3,6-Anhydro-2,8-dideoxy-L-glycero-L-ido-octono-1,4-lactone monohydrate
;
_chemical_name_common            '(-)-Asperilactone B monohydrate'
_chemical_melting_point          365
_chemical_formula_moiety         'C8 H14 O6'
_chemical_formula_sum            'C8 H14 O6'
_chemical_formula_weight         206.19
_chemical_absolute_configuration rmad
_chemical_enantioexcess_bulk     1
_chemical_enantioexcess_bulk_technique OA
_chemical_optical_rotation       '[\a]^25^~D~ = -41.4 (c = 0.5, Me~2~CO)'

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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. 
;

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'

_cell_length_a                   16.5089(3)
_cell_length_b                   6.85830(11)
_cell_length_c                   8.93440(19)
_cell_angle_alpha                90
_cell_angle_beta                 104.846(2)
_cell_angle_gamma                90
_cell_volume                     977.81(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4453
_cell_measurement_theta_min      5.1170
_cell_measurement_theta_max      71.9350

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.770
_exptl_crystal_size_mid          0.403
_exptl_crystal_size_min          0.116
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69819
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.41.109a (Rigaku Oxford Diffraction, 2021) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      295(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     56.00 109.00   1.00    3.00    --   36.41-178.00  90.00   53
  2  ω      7.00 108.00   1.00    3.00    --   36.41  19.00  60.00  101
  3  ω    -31.00  53.00   1.00    3.00    --   36.41 -57.00 120.00   84
  4  ω      1.00  75.00   1.00    3.00    --   36.41 -99.00  90.00   74
  5  ω      1.00  75.00   1.00    3.00    --   36.41 -99.00 -90.00   74
  6  ω     61.00 109.00   1.00    3.00    --   36.41 178.00 -60.00   48
  7  ω      1.00  75.00   1.00    3.00    --   36.41 -99.00  60.00   74
  8  ω      7.00 108.00   1.00    3.00    --   36.41  19.00  90.00  101
  9  ω     91.00 176.00   1.00   12.00    --  108.00  45.00   0.00   85
 10  ω     90.00 175.00   1.00   12.00    --  108.00  61.00 -90.00   85
 11  ω     91.00 176.00   1.00   12.00    --  108.00  45.00 -30.00   85
 12  ω     90.00 175.00   1.00   12.00    --  108.00  61.00-180.00   85
 13  ω     70.00 178.00   1.00   12.00    --  108.00  15.00   0.00  108
 14  ω     41.00 126.00   1.00   12.00    --  108.00 -61.00-180.00   85
 15  ω     90.00 175.00   1.00   12.00    --  108.00  61.00 -30.00   85
 16  ω     39.00 106.00   1.00   12.00    --  108.00 -94.00 -60.00   67
 17  ω     39.00 106.00   1.00   12.00    --  108.00 -94.00 150.00   67
 18  ω     41.00 126.00   1.00   12.00    --  108.00 -61.00  60.00   85
 19  ω    104.00 178.00   1.00   12.00    --  108.00 111.00  90.00   74
 20  ω     38.00 109.00   1.00   12.00    --  108.00-111.00 120.00   71
 21  ω     91.00 176.00   1.00   12.00    --  108.00  45.00-120.00   85
 22  ω     90.00 175.00   1.00   12.00    --  108.00  61.00 -60.00   85
 23  ω     91.00 176.00   1.00   12.00    --  108.00  45.00 -60.00   85
 24  ω     38.00 109.00   1.00   12.00    --  108.00-111.00  90.00   71
 25  ω     38.00 129.00   1.00   12.00    --  108.00 -30.00  60.00   91
 26  ω     20.00  86.00   1.00    3.00    --   36.41  57.00-180.00   66
 27  φ   -180.00  90.00   1.00    0.50   0.00   0.00   0.00    --   270
;
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0616949000
_diffrn_orient_matrix_UB_12      -0.1725383000
_diffrn_orient_matrix_UB_13      -0.0223296000
_diffrn_orient_matrix_UB_21      -0.0391155000
_diffrn_orient_matrix_UB_22      0.0655711000
_diffrn_orient_matrix_UB_23      -0.1679353000
_diffrn_orient_matrix_UB_31      0.0630985000
_diffrn_orient_matrix_UB_32      -0.1280606000
_diffrn_orient_matrix_UB_33      -0.0559191000
_diffrn_reflns_number            4973
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.121
_diffrn_reflns_theta_max         71.851
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1874
_reflns_number_gt                1847
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.984

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'ShelXle (Hübschle et al., 2011)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+0.2791P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   .
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0157(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 812 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_number_reflns         1874
_refine_ls_number_parameters     142
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.2915(2) 0.1838(4) 0.6583(3) 0.0897(9) Uani 1 1 d . . . . .
O6 O 0.42562(10) 0.1924(3) 0.3055(2) 0.0569(5) Uani 1 1 d . . . . .
O4 O 0.25225(11) 0.1879(3) 0.4019(2) 0.0541(5) Uani 1 1 d . . . . .
O5 O 0.29380(12) 0.2290(3) 0.02211(19) 0.0530(5) Uani 1 1 d . . . . .
H5A H 0.250(3) 0.197(7) -0.021(3) 0.080 Uiso 1 1 calc R U . . .
O7 O 0.37364(11) 0.6510(3) 0.1079(2) 0.0554(5) Uani 1 1 d . . . . .
H7A H 0.3972(19) 0.724(6) 0.066(5) 0.083 Uiso 1 1 calc R U . . .
C1 C 0.30537(18) 0.1387(4) 0.5373(3) 0.0539(6) Uani 1 1 d . . . . .
C2 C 0.37786(16) 0.0271(4) 0.5098(3) 0.0537(6) Uani 1 1 d . . . . .
H2A H 0.374821 -0.108766 0.537991 0.064 Uiso 1 1 calc R U . . .
H2AB H 0.430394 0.081250 0.570073 0.064 Uiso 1 1 calc R U . . .
C3 C 0.37105(14) 0.0465(3) 0.3393(3) 0.0440(5) Uani 1 1 d . . . . .
H3 H 0.379889 -0.079322 0.293933 0.053 Uiso 1 1 calc R U . . .
C4 C 0.28168(14) 0.1212(3) 0.2712(3) 0.0423(5) Uani 1 1 d . . . . .
H4 H 0.245173 0.020639 0.211304 0.051 Uiso 1 1 calc R U . . .
C5 C 0.29219(13) 0.2942(3) 0.1715(3) 0.0394(5) Uani 1 1 d . . . . .
H5 H 0.249229 0.394011 0.167561 0.047 Uiso 1 1 calc R U . . .
C6 C 0.37935(13) 0.3663(3) 0.2543(2) 0.0384(5) Uani 1 1 d . . . . .
H6 H 0.375605 0.442696 0.344978 0.046 Uiso 1 1 calc R U . . .
C7 C 0.42533(14) 0.4852(3) 0.1589(3) 0.0409(5) Uani 1 1 d . . . . .
H7 H 0.430028 0.408840 0.068784 0.049 Uiso 1 1 calc R U . . .
C8 C 0.51201(18) 0.5451(5) 0.2514(4) 0.0676(8) Uani 1 1 d . . . . .
H8A H 0.536975 0.628920 0.189667 0.101 Uiso 1 1 calc R U . . .
H8B H 0.546157 0.431019 0.280276 0.101 Uiso 1 1 calc R U . . .
H8C H 0.507847 0.613232 0.343018 0.101 Uiso 1 1 calc R U . . .
O8 O 0.41396(15) 0.9735(5) -0.0501(3) 0.0785(7) Uani 1 1 d D . . . .
H81 H 0.463(2) 0.976(15) -0.001(10) 0.118 Uiso 0.5 1 d D U P A 1
H82 H 0.405(7) 1.031(13) -0.138(6) 0.118 Uiso 0.5 1 d D U P B 2
H83 H 0.389(3) 1.049(7) -0.006(5) 0.118 Uiso 1 1 d D U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 1.201(3) . ?
O6 C6 1.427(3) . ?
O6 C3 1.429(3) . ?
O4 C1 1.342(3) . ?
O4 C4 1.449(3) . ?
O5 C5 1.414(3) . ?
O5 H5A 0.76(5) . ?
O7 C7 1.424(3) . ?
O7 H7A 0.79(5) . ?
C1 C2 1.493(4) . ?
C2 C3 1.504(3) . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C3 C4 1.533(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.520(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.522(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.516(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.514(3) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O8 H81 0.82(3) . ?
O8 H82 0.85(3) . ?
O8 H83 0.82(2) . ?

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
C6 O6 C3 109.76(16) . . ?
C1 O4 C4 111.71(19) . . ?
C5 O5 H5A 109.5 . . ?
C7 O7 H7A 109.5 . . ?
O1 C1 O4 121.0(3) . . ?
O1 C1 C2 128.7(3) . . ?
O4 C1 C2 110.3(2) . . ?
C1 C2 C3 105.4(2) . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2AB 110.7 . . ?
C3 C2 H2AB 110.7 . . ?
H2A C2 H2AB 108.8 . . ?
O6 C3 C2 112.8(2) . . ?
O6 C3 C4 106.07(18) . . ?
C2 C3 C4 104.24(19) . . ?
O6 C3 H3 111.1 . . ?
C2 C3 H3 111.1 . . ?
C4 C3 H3 111.1 . . ?
O4 C4 C5 109.78(19) . . ?
O4 C4 C3 105.84(19) . . ?
C5 C4 C3 104.52(18) . . ?
O4 C4 H4 112.1 . . ?
C5 C4 H4 112.1 . . ?
C3 C4 H4 112.1 . . ?
O5 C5 C4 109.82(19) . . ?
O5 C5 C6 108.52(18) . . ?
C4 C5 C6 101.78(17) . . ?
O5 C5 H5 112.1 . . ?
C4 C5 H5 112.1 . . ?
C6 C5 H5 112.1 . . ?
O6 C6 C7 109.02(17) . . ?
O6 C6 C5 104.24(17) . . ?
C7 C6 C5 116.64(18) . . ?
O6 C6 H6 108.9 . . ?
C7 C6 H6 108.9 . . ?
C5 C6 H6 108.9 . . ?
O7 C7 C8 111.3(2) . . ?
O7 C7 C6 105.30(18) . . ?
C8 C7 C6 112.21(19) . . ?
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 107(4) . . ?
H82 O8 H83 99(4) . . ?

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 179.2(3) . . . . ?
C4 O4 C1 C2 -0.9(3) . . . . ?
O1 C1 C2 C3 -169.6(3) . . . . ?
O4 C1 C2 C3 10.5(3) . . . . ?
C6 O6 C3 C2 -100.8(2) . . . . ?
C6 O6 C3 C4 12.7(3) . . . . ?
C1 C2 C3 O6 99.6(2) . . . . ?
C1 C2 C3 C4 -15.1(3) . . . . ?
C1 O4 C4 C5 -121.2(2) . . . . ?
C1 O4 C4 C3 -8.9(3) . . . . ?
O6 C3 C4 O4 -104.6(2) . . . . ?
C2 C3 C4 O4 14.7(2) . . . . ?
O6 C3 C4 C5 11.3(2) . . . . ?
C2 C3 C4 C5 130.6(2) . . . . ?
O4 C4 C5 O5 -160.97(17) . . . . ?
C3 C4 C5 O5 85.9(2) . . . . ?
O4 C4 C5 C6 84.2(2) . . . . ?
C3 C4 C5 C6 -28.9(2) . . . . ?
C3 O6 C6 C7 -156.88(19) . . . . ?
C3 O6 C6 C5 -31.7(2) . . . . ?
O5 C5 C6 O6 -78.9(2) . . . . ?
C4 C5 C6 O6 36.9(2) . . . . ?
O5 C5 C6 C7 41.4(3) . . . . ?
C4 C5 C6 C7 157.17(18) . . . . ?
O6 C6 C7 O7 177.83(18) . . . . ?
C5 C6 C7 O7 60.2(2) . . . . ?
O6 C6 C7 C8 -61.0(3) . . . . ?
C5 C6 C7 C8 -178.6(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 0.76 2.02 2.762(3) 167.8 4_545 yes
O7 H7A O8 0.79 2.06 2.795(4) 156.8 . yes
O8 H81^a O8 0.82(3) 1.96(3) 2.751(5) 162(9) 2_655 yes
O8 H82^b O1 0.85(3) 2.48(7) 3.202(4) 142(8) 1_564 yes
O8 H83 O5 0.82(2) 2.06(3) 2.842(3) 158(5) 1_565 yes

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.037

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8
_database_code_depnum_ccdc_archive 'CCDC 2333777'
loop_
_audit_author_name
_audit_author_address
'Marko Rodic'
;University of Novi Sad
Serbia
;
_audit_update_record             
;
2024-02-19 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
#exp_code: data_SD76-DJ4_2631_222_a  

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
; 3,6-Anhydro-2,8-dideoxy-L-glycero-D-ido-octono-1,4-lactone 
;
_chemical_name_common            
; 3,6-Anhydro-2,8-dideoxy-L-glycero-D-ido-octono-1,4-lactone 
;
_chemical_melting_point          401
_chemical_formula_moiety         'C8 H12 O5'
_chemical_formula_sum            'C8 H12 O5'
_chemical_formula_weight         188.18
_chemical_absolute_configuration rmad
_chemical_enantioexcess_bulk     1
_chemical_enantioexcess_bulk_technique OA
_chemical_optical_rotation       '[\a]^25^~D~ = +38.4 (c = 0.5, Me~2~CO)'

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.37102(6)
_cell_length_b                   12.47818(12)
_cell_length_c                   26.7627(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1793.65(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    10051
_cell_measurement_theta_min      3.2620
_cell_measurement_theta_max      71.8730

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.622
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50076
_exptl_absorpt_correction_T_max  1.00000
_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. 
;
_diffrn_ambient_temperature      295(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  74.00   1.00   10.00    --   36.28 -99.00 -90.00   73
  2  ω    -18.00  63.00   1.00   10.00    --   36.28 -77.00-150.00   81
  3  ω      1.00  74.00   1.00   10.00    --   36.28 -99.00  30.00   73
  4  ω    -18.00  63.00   1.00   10.00    --   36.28 -77.00 120.00   81
  5  ω     56.00 109.00   1.00   10.00    --   36.28-178.00   0.00   53
  6  ω     39.00 106.00   1.00   40.00    --  108.00 -94.00 -60.00   67
  7  ω    101.00 176.00   1.00   40.00    --  108.00  77.00-150.00   75
  8  ω     39.00 106.00   1.00   40.00    --  108.00 -94.00  90.00   67
  9  ω     41.00 126.00   1.00   40.00    --  108.00 -61.00-150.00   85
 10  ω     40.00 125.00   1.00   40.00    --  108.00 -45.00 -60.00   85
 11  ω     39.00 106.00   1.00   40.00    --  108.00 -94.00 150.00   67
 12  ω     41.00 126.00   1.00   40.00    --  108.00 -61.00 120.00   85
 13  ω     70.00 178.00   1.00   40.00    --  108.00  15.00 -30.00  108
 14  ω     20.00 104.00   1.00   10.00    --   36.28  57.00 -90.00   84
 15  ω     20.00 104.00   1.00   10.00    --   36.28  57.00   0.00   84
 16  ω     20.00 104.00   1.00   10.00    --   36.28  57.00-180.00   84
 17  ω     20.00 104.00   1.00   10.00    --   36.28  57.00  60.00   84
 18  ω     85.00 175.00   1.00   40.00    --  108.00  71.00-129.00   90
 19  ω     91.00 176.00   1.00   40.00    --  108.00  45.00   0.00   85
 20  ω     70.00 178.00   1.00   40.00    --  108.00  15.00-180.00  108
 21  ω     91.00 176.00   1.00   40.00    --  108.00  45.00  90.00   85
 22  ω     70.00 178.00   1.00   40.00    --  108.00  15.00  90.00  108
 23  ω     39.00 106.00   1.00   40.00    --  108.00 -94.00   0.00   67
 24  ω     87.00 178.00   1.00   40.00    --  108.00  30.00-150.00   91
 25  ω     91.00 176.00   1.00   40.00    --  108.00  45.00 -90.00   85
 26  ω     17.00 106.00   1.00   10.00    --   36.28  37.00 150.00   89
 27  ω     20.00 104.00   1.00   10.00    --   36.28  57.00 -30.00   84
 28  ω    -31.00  53.00   1.00   10.00    --   36.28 -57.00 -60.00   84
 29  ω    -33.00  55.00   1.00   10.00    --   36.28 -37.00   0.00   88
 30  ω     90.00 155.00   1.00   40.00    --  108.00  61.00 -30.00   65
;
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2268075000
_diffrn_orient_matrix_UB_12      -0.0518766000
_diffrn_orient_matrix_UB_13      -0.0256577000
_diffrn_orient_matrix_UB_21      0.0557309000
_diffrn_orient_matrix_UB_22      -0.1064572000
_diffrn_orient_matrix_UB_23      0.0269296000
_diffrn_orient_matrix_UB_31      -0.1665101000
_diffrn_orient_matrix_UB_32      0.0350280000
_diffrn_orient_matrix_UB_33      0.0439097000

_diffrn_reflns_number            19203
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.303
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_full        66.596
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3176
_reflns_number_gt                3032
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'ShelXle (Hübschle et al., 2011)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+0.3008P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   .
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1195 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_number_reflns         3176
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1A O 1.0026(4) 0.70880(14) 0.44037(8) 0.0756(6) Uani 1 1 d . . . . .
O4A O 1.0627(3) 0.54282(13) 0.46809(7) 0.0581(4) Uani 1 1 d . . . . .
O5A O 0.8807(3) 0.26359(13) 0.48277(6) 0.0536(4) Uani 1 1 d . . . . .
H51A H 1.010(5) 0.2349(19) 0.4979(11) 0.080 Uiso 1 1 calc R U . . .
O6A O 0.5690(3) 0.42538(12) 0.43575(6) 0.0501(4) Uani 1 1 d . . . . .
O7A O 0.5472(4) 0.31000(14) 0.34164(6) 0.0636(5) Uani 1 1 d . . . . .
H7A H 0.436(7) 0.355(3) 0.3510(5) 0.095 Uiso 1 1 calc R U . . .
C1A C 0.9149(5) 0.62824(19) 0.45746(9) 0.0522(5) Uani 1 1 d . . . . .
C2A C 0.6528(4) 0.60356(18) 0.47084(9) 0.0501(5) Uani 1 1 d . . . . .
H21A H 0.541106 0.623637 0.443931 0.060 Uiso 1 1 calc R U . . .
H22A H 0.604095 0.641635 0.500890 0.060 Uiso 1 1 calc R U . . .
C3A C 0.6467(4) 0.48346(17) 0.47936(8) 0.0428(5) Uani 1 1 d . . . . .
H3A H 0.545305 0.464825 0.508530 0.051 Uiso 1 1 calc R U . . .
C4A C 0.9206(4) 0.45413(18) 0.48734(8) 0.0463(5) Uani 1 1 d . . . . .
H4A H 0.957911 0.440002 0.522577 0.056 Uiso 1 1 calc R U . . .
C5A C 0.9595(4) 0.35554(17) 0.45503(8) 0.0442(5) Uani 1 1 d . . . . .
H5A H 1.131925 0.349031 0.443445 0.053 Uiso 1 1 calc R U . . .
C6A C 0.7803(4) 0.37498(17) 0.41252(8) 0.0420(5) Uani 1 1 d . . . . .
H6A H 0.855987 0.425697 0.389049 0.050 Uiso 1 1 calc R U . . .
C7A C 0.6918(5) 0.27781(18) 0.38378(8) 0.0506(5) Uani 1 1 d . . . . .
H71A H 0.589270 0.233086 0.405741 0.061 Uiso 1 1 calc R U . . .
C8A C 0.9056(6) 0.2115(2) 0.36369(12) 0.0773(8) Uani 1 1 d . . . . .
H81A H 0.841290 0.154539 0.343343 0.116 Uiso 1 1 calc R U . . .
H82A H 0.998285 0.181817 0.391058 0.116 Uiso 1 1 calc R U . . .
H83A H 1.012806 0.256184 0.343937 0.116 Uiso 1 1 calc R U . . .
O1B O 0.8586(5) 0.46771(18) 0.09698(8) 0.0848(7) Uani 1 1 d . . . . .
O4B O 0.7643(4) 0.40298(14) 0.17172(7) 0.0679(5) Uani 1 1 d . . . . .
O5B O 0.4867(5) 0.20281(17) 0.25434(7) 0.0765(6) Uani 1 1 d . . . . .
H5B H 0.496(5) 0.232(3) 0.2815(14) 0.115 Uiso 1 1 calc R U . . .
O6B O 0.4987(3) 0.18878(12) 0.14660(6) 0.0562(4) Uani 1 1 d . . . . .
O7B O 0.7458(3) -0.00986(13) 0.14640(6) 0.0554(4) Uani 1 1 d . . . . .
H7B H 0.646(6) 0.012(2) 0.1248(10) 0.083 Uiso 1 1 calc R U . . .
C1B C 0.7167(6) 0.4188(2) 0.12264(10) 0.0619(7) Uani 1 1 d . . . . .
C2B C 0.4769(6) 0.3663(2) 0.10877(12) 0.0730(8) Uani 1 1 d . . . . .
H21B H 0.496354 0.323509 0.078762 0.088 Uiso 1 1 calc R U . . .
H22B H 0.348165 0.419439 0.103067 0.088 Uiso 1 1 calc R U . . .
C3B C 0.4123(5) 0.2965(2) 0.15283(10) 0.0619(6) Uani 1 1 d . . . . .
H3B H 0.233670 0.298661 0.160196 0.074 Uiso 1 1 calc R U . . .
C4B C 0.5657(6) 0.3429(2) 0.19566(10) 0.0637(7) Uani 1 1 d . . . . .
H4B H 0.465303 0.387935 0.217907 0.076 Uiso 1 1 calc R U . . .
C5B C 0.6697(5) 0.2460(2) 0.22220(9) 0.0590(7) Uani 1 1 d . . . . .
H51B H 0.825490 0.261872 0.239760 0.071 Uiso 1 1 calc R U . . .
C6B C 0.7078(4) 0.16965(18) 0.17874(8) 0.0481(5) Uani 1 1 d . . . . .
H6B H 0.860877 0.189419 0.161057 0.058 Uiso 1 1 calc R U . . .
C7B C 0.7170(4) 0.0519(2) 0.19127(8) 0.0496(5) Uani 1 1 d . . . . .
H71B H 0.561689 0.031170 0.207894 0.060 Uiso 1 1 calc R U . . .
C8B C 0.9334(6) 0.0241(3) 0.22439(10) 0.0745(8) Uani 1 1 d . . . . .
H81B H 0.945874 -0.052360 0.227436 0.112 Uiso 1 1 calc R U . . .
H82B H 0.908535 0.055099 0.256844 0.112 Uiso 1 1 calc R U . . .
H83B H 1.084043 0.051844 0.210064 0.112 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
O1A C1A 1.201(3) . ?
O4A C1A 1.359(3) . ?
O4A C4A 1.440(3) . ?
O5A C5A 1.431(3) . ?
O5A H51A 0.88(3) . ?
O6A C3A 1.436(3) . ?
O6A C6A 1.439(3) . ?
O7A C7A 1.427(3) . ?
O7A H7A 0.86(4) . ?
C1A C2A 1.485(4) . ?
C2A C3A 1.516(3) . ?
C2A H21A 0.9700 . ?
C2A H22A 0.9700 . ?
C3A C4A 1.531(3) . ?
C3A H3A 0.9800 . ?
C4A C5A 1.518(3) . ?
C4A H4A 0.9800 . ?
C5A C6A 1.510(3) . ?
C5A H5A 0.9800 . ?
C6A C7A 1.512(3) . ?
C6A H6A 0.9800 . ?
C7A C8A 1.514(4) . ?
C7A H71A 0.9800 . ?
C8A H81A 0.9600 . ?
C8A H82A 0.9600 . ?
C8A H83A 0.9600 . ?
O1B C1B 1.194(3) . ?
O4B C1B 1.352(3) . ?
O4B C4B 1.452(3) . ?
O5B C5B 1.413(3) . ?
O5B H5B 0.81(4) . ?
O6B C3B 1.431(3) . ?
O6B C6B 1.435(3) . ?
O7B C7B 1.435(3) . ?
O7B H7B 0.83(4) . ?
C1B C2B 1.492(4) . ?
C2B C3B 1.506(4) . ?
C2B H21B 0.9700 . ?
C2B H22B 0.9700 . ?
C3B C4B 1.526(4) . ?
C3B H3B 0.9800 . ?
C4B C5B 1.510(4) . ?
C4B H4B 0.9800 . ?
C5B C6B 1.517(3) . ?
C5B H51B 0.9800 . ?
C6B C7B 1.508(3) . ?
C6B H6B 0.9800 . ?
C7B C8B 1.502(4) . ?
C7B H71B 0.9800 . ?
C8B H81B 0.9600 . ?
C8B H82B 0.9600 . ?
C8B H83B 0.9600 . ?

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
C1A O4A C4A 111.59(18) . . ?
C5A O5A H51A 109.5 . . ?
C3A O6A C6A 110.04(16) . . ?
C7A O7A H7A 109.5 . . ?
O1A C1A O4A 120.5(2) . . ?
O1A C1A C2A 129.6(2) . . ?
O4A C1A C2A 109.9(2) . . ?
C1A C2A C3A 105.15(19) . . ?
C1A C2A H21A 110.7 . . ?
C3A C2A H21A 110.7 . . ?
C1A C2A H22A 110.7 . . ?
C3A C2A H22A 110.7 . . ?
H21A C2A H22A 108.8 . . ?
O6A C3A C2A 112.52(18) . . ?
O6A C3A C4A 105.80(17) . . ?
C2A C3A C4A 103.70(18) . . ?
O6A C3A H3A 111.5 . . ?
C2A C3A H3A 111.5 . . ?
C4A C3A H3A 111.5 . . ?
O4A C4A C5A 110.24(18) . . ?
O4A C4A C3A 106.01(17) . . ?
C5A C4A C3A 104.27(17) . . ?
O4A C4A H4A 112.0 . . ?
C5A C4A H4A 112.0 . . ?
C3A C4A H4A 112.0 . . ?
O5A C5A C6A 109.34(18) . . ?
O5A C5A C4A 108.27(17) . . ?
C6A C5A C4A 102.19(17) . . ?
O5A C5A H5A 112.2 . . ?
C6A C5A H5A 112.2 . . ?
C4A C5A H5A 112.2 . . ?
O6A C6A C5A 104.33(16) . . ?
O6A C6A C7A 108.82(18) . . ?
C5A C6A C7A 117.03(18) . . ?
O6A C6A H6A 108.8 . . ?
C5A C6A H6A 108.8 . . ?
C7A C6A H6A 108.8 . . ?
O7A C7A C6A 110.31(18) . . ?
O7A C7A C8A 106.6(2) . . ?
C6A C7A C8A 112.4(2) . . ?
O7A C7A H71A 109.2 . . ?
C6A C7A H71A 109.2 . . ?
C8A C7A H71A 109.2 . . ?
C7A C8A H81A 109.5 . . ?
C7A C8A H82A 109.5 . . ?
H81A C8A H82A 109.5 . . ?
C7A C8A H83A 109.5 . . ?
H81A C8A H83A 109.5 . . ?
H82A C8A H83A 109.5 . . ?
C1B O4B C4B 111.4(2) . . ?
C5B O5B H5B 109.5 . . ?
C3B O6B C6B 109.88(18) . . ?
C7B O7B H7B 109.5 . . ?
O1B C1B O4B 120.8(3) . . ?
O1B C1B C2B 129.3(3) . . ?
O4B C1B C2B 109.9(2) . . ?
C1B C2B C3B 104.9(2) . . ?
C1B C2B H21B 110.8 . . ?
C3B C2B H21B 110.8 . . ?
C1B C2B H22B 110.8 . . ?
C3B C2B H22B 110.8 . . ?
H21B C2B H22B 108.8 . . ?
O6B C3B C2B 112.2(2) . . ?
O6B C3B C4B 105.6(2) . . ?
C2B C3B C4B 104.1(2) . . ?
O6B C3B H3B 111.5 . . ?
C2B C3B H3B 111.5 . . ?
C4B C3B H3B 111.5 . . ?
O4B C4B C5B 110.5(2) . . ?
O4B C4B C3B 105.1(2) . . ?
C5B C4B C3B 104.4(2) . . ?
O4B C4B H4B 112.1 . . ?
C5B C4B H4B 112.1 . . ?
C3B C4B H4B 112.1 . . ?
O5B C5B C4B 109.6(2) . . ?
O5B C5B C6B 108.7(2) . . ?
C4B C5B C6B 101.09(19) . . ?
O5B C5B H51B 112.3 . . ?
C4B C5B H51B 112.3 . . ?
C6B C5B H51B 112.3 . . ?
O6B C6B C7B 108.72(18) . . ?
O6B C6B C5B 104.4(2) . . ?
C7B C6B C5B 116.46(19) . . ?
O6B C6B H6B 109.0 . . ?
C7B C6B H6B 109.0 . . ?
C5B C6B H6B 109.0 . . ?
O7B C7B C8B 106.7(2) . . ?
O7B C7B C6B 109.90(17) . . ?
C8B C7B C6B 112.4(2) . . ?
O7B C7B H71B 109.3 . . ?
C8B C7B H71B 109.3 . . ?
C6B C7B H71B 109.3 . . ?
C7B C8B H81B 109.5 . . ?
C7B C8B H82B 109.5 . . ?
H81B C8B H82B 109.5 . . ?
C7B C8B H83B 109.5 . . ?
H81B C8B H83B 109.5 . . ?
H82B C8B H83B 109.5 . . ?

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
C4A O4A C1A O1A -179.0(2) . . . . ?
C4A O4A C1A C2A 1.9(3) . . . . ?
O1A C1A C2A C3A 167.6(2) . . . . ?
O4A C1A C2A C3A -13.3(3) . . . . ?
C6A O6A C3A C2A 104.6(2) . . . . ?
C6A O6A C3A C4A -7.9(2) . . . . ?
C1A C2A C3A O6A -95.4(2) . . . . ?
C1A C2A C3A C4A 18.4(2) . . . . ?
C1A O4A C4A C5A 122.55(19) . . . . ?
C1A O4A C4A C3A 10.3(2) . . . . ?
O6A C3A C4A O4A 100.98(19) . . . . ?
C2A C3A C4A O4A -17.6(2) . . . . ?
O6A C3A C4A C5A -15.4(2) . . . . ?
C2A C3A C4A C5A -133.99(18) . . . . ?
O4A C4A C5A O5A 162.68(17) . . . . ?
C3A C4A C5A O5A -83.9(2) . . . . ?
O4A C4A C5A C6A -82.0(2) . . . . ?
C3A C4A C5A C6A 31.4(2) . . . . ?
C3A O6A C6A C5A 28.3(2) . . . . ?
C3A O6A C6A C7A 153.94(17) . . . . ?
O5A C5A C6A O6A 78.1(2) . . . . ?
C4A C5A C6A O6A -36.5(2) . . . . ?
O5A C5A C6A C7A -42.2(2) . . . . ?
C4A C5A C6A C7A -156.77(19) . . . . ?
O6A C6A C7A O7A 68.7(2) . . . . ?
C5A C6A C7A O7A -173.46(19) . . . . ?
O6A C6A C7A C8A -172.5(2) . . . . ?
C5A C6A C7A C8A -54.6(3) . . . . ?
C4B O4B C1B O1B 179.2(3) . . . . ?
C4B O4B C1B C2B -1.5(3) . . . . ?
O1B C1B C2B C3B 167.2(3) . . . . ?
O4B C1B C2B C3B -11.9(3) . . . . ?
C6B O6B C3B C2B 107.2(2) . . . . ?
C6B O6B C3B C4B -5.6(3) . . . . ?
C1B C2B C3B O6B -94.1(3) . . . . ?
C1B C2B C3B C4B 19.6(3) . . . . ?
C1B O4B C4B C5B 126.2(2) . . . . ?
C1B O4B C4B C3B 14.2(3) . . . . ?
O6B C3B C4B O4B 97.7(2) . . . . ?
C2B C3B C4B O4B -20.6(3) . . . . ?
O6B C3B C4B C5B -18.6(3) . . . . ?
C2B C3B C4B C5B -136.9(2) . . . . ?
O4B C4B C5B O5B 166.70(19) . . . . ?
C3B C4B C5B O5B -80.8(2) . . . . ?
O4B C4B C5B C6B -78.7(2) . . . . ?
C3B C4B C5B C6B 33.9(3) . . . . ?
C3B O6B C6B C7B 152.5(2) . . . . ?
C3B O6B C6B C5B 27.6(2) . . . . ?
O5B C5B C6B O6B 77.6(2) . . . . ?
C4B C5B C6B O6B -37.6(2) . . . . ?
O5B C5B C6B C7B -42.3(3) . . . . ?
C4B C5B C6B C7B -157.5(2) . . . . ?
O6B C6B C7B O7B 60.6(2) . . . . ?
C5B C6B C7B O7B 178.2(2) . . . . ?
O6B C6B C7B C8B 179.2(2) . . . . ?
C5B C6B C7B C8B -63.2(3) . . . . ?

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
O5A H51A O5A 0.88 2.06 2.8597(11) 151.0 4_556 yes
O7A H7A O7B 0.86 1.95 2.762(2) 158.0 3_655 yes
O5B H5B O7A 0.81 1.90 2.712(2) 173.1 . yes
O7B H7B O6A 0.83 2.27 2.889(2) 131.5 3_645 yes

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10
_database_code_depnum_ccdc_archive 'CCDC 2333779'
loop_
_audit_author_name
_audit_author_address
'Marko Rodic'
;University of Novi Sad
Serbia
;
_audit_update_record             
;
2024-02-19 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
#exp_code: data_SD43_2581_mP_a  

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 O5'
_chemical_formula_sum            'C8 H12 O5'
_chemical_formula_weight         188.18
_chemical_absolute_configuration rm
_chemical_enantioexcess_bulk     1
_chemical_enantioexcess_bulk_technique OA
_chemical_optical_rotation       ?

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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5474(5)
_cell_length_b                   5.4514(3)
_cell_length_c                   9.7185(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.269(7)
_cell_angle_gamma                90
_cell_volume                     427.47(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4551
_cell_measurement_theta_min      2.7350
_cell_measurement_theta_max      28.3330

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.804
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91585
_exptl_absorpt_correction_T_max  1.00000
_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
;
_diffrn_ambient_temperature      295(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00   1.00   1.00   20.00    --  -15.69 -57.00-180.00   84
  2  ω    -39.00  11.00   1.00   20.00    --  -15.69 -77.00 120.00   50
  3  ω    -39.00  11.00   1.00   20.00    --  -15.69 -77.00  30.00   50
  4  ω    -42.00  18.00   1.00   20.00    --  -15.69  77.00 -60.00   60
  5  ω    -53.00  86.00   1.00   20.00    --   16.71   0.00-120.00  139
  6  ω    -20.00  55.00   1.00   20.00    --   16.71 -99.00  60.00   75
  7  ω    -39.00  11.00   1.00   20.00    --  -15.69 -77.00-120.00   50
  8  ω    -39.00  11.00   1.00   20.00    --  -15.69 -77.00 -30.00   50
  9  ω    -42.00  18.00   1.00   20.00    --  -15.69  77.00 120.00   60
 10  ω    -39.00  43.00   1.00   20.00    --   16.71 -77.00-150.00   82
 11  ω    -55.00  46.00   1.00   20.00    --   16.71 -19.00 120.00  101
 12  ω    -39.00  11.00   1.00   20.00    --  -15.69 -77.00   0.00   50
 13  ω    -20.00  55.00   1.00   20.00    --   16.71 -99.00 -90.00   75
 14  ω    -39.00  43.00   1.00   20.00    --   16.71 -77.00-120.00   82
 15  ω     -2.00  86.00   1.00   20.00    --   16.71  37.00 -30.00   88
;
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0673457000
_diffrn_orient_matrix_UB_12      -0.0099346000
_diffrn_orient_matrix_UB_13      -0.0269973000
_diffrn_orient_matrix_UB_21      0.0561923000
_diffrn_orient_matrix_UB_22      0.0255020000
_diffrn_orient_matrix_UB_23      0.0705954000
_diffrn_orient_matrix_UB_31      0.0059368000
_diffrn_orient_matrix_UB_32      -0.1272228000
_diffrn_orient_matrix_UB_33      0.0162685000
_diffrn_reflns_number            10436
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.220
_diffrn_reflns_theta_max         29.393
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2091
_reflns_number_gt                1835
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_max     0.843
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'ShelXle (Hübschle et al., 2011)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²+0.0518P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   .
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 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    -2.4(5) 

 The absolute structure parameter is meaningless because the compound is a 
 weak anomalous scatterer.
;
_refine_ls_number_reflns         2091
_refine_ls_number_parameters     123
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.0668(2) 0.3410(4) 0.16759(19) 0.0464(5) Uani 1 1 d . . . . .
O4 O 0.91099(17) 0.3613(3) 0.31077(15) 0.0311(4) Uani 1 1 d . . . . .
O5 O 0.7400(2) 0.2313(3) 0.48783(18) 0.0399(4) Uani 1 1 d . . . . .
H5 H 0.672(3) 0.190(3) 0.517(3) 0.060 Uiso 1 1 calc R U . . .
O6 O 0.4095(2) 0.4156(3) 0.35087(18) 0.0397(4) Uani 1 1 d . . . . .
H6 H 0.323(3) 0.377(7) 0.284(3) 0.060 Uiso 1 1 calc R U . . .
O7 O 0.65292(17) 0.7363(3) 0.15818(16) 0.0337(4) Uani 1 1 d . . . . .
C1 C 0.9823(2) 0.4634(4) 0.2194(2) 0.0313(5) Uani 1 1 d . . . . .
C2 C 0.9423(3) 0.7318(4) 0.2007(2) 0.0347(5) Uani 1 1 d . . . . .
H2A H 0.901381 0.776057 0.098343 0.042 Uiso 1 1 calc R U . . .
H2B H 1.039298 0.830378 0.249529 0.042 Uiso 1 1 calc R U . . .
C3 C 0.8091(3) 0.7671(4) 0.2706(2) 0.0310(5) Uani 1 1 d . . . . .
H3 H 0.817929 0.927089 0.318500 0.037 Uiso 1 1 calc R U . . .
C4 C 0.8455(3) 0.5556(4) 0.3802(2) 0.0282(5) Uani 1 1 d . . . . .
H4 H 0.932605 0.607099 0.469497 0.034 Uiso 1 1 calc R U . . .
C5 C 0.6981(3) 0.4644(4) 0.4196(2) 0.0288(4) Uani 1 1 d . . . . .
H5A H 0.682119 0.577594 0.492163 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5390(2) 0.4613(4) 0.2909(2) 0.0277(4) Uani 1 1 d . . . . .
H6A H 0.542463 0.329594 0.223386 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5174(3) 0.7095(4) 0.2134(2) 0.0318(5) Uani 1 1 d . . . . .
H7 H 0.522274 0.840710 0.283650 0.038 Uiso 1 1 calc R U . . .
C8 C 0.3594(3) 0.7333(5) 0.0852(3) 0.0462(6) Uani 1 1 d . . . . .
H8A H 0.356501 0.890927 0.040411 0.069 Uiso 1 1 calc R U . . .
H8B H 0.265752 0.717386 0.118322 0.069 Uiso 1 1 calc R U . . .
H8C H 0.355560 0.606729 0.015514 0.069 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 1.209(3) . ?
O4 C1 1.351(3) . ?
O4 C4 1.463(3) . ?
O5 C5 1.423(3) . ?
O5 H5 0.76(3) . ?
O6 C6 1.432(2) . ?
O6 H6 0.83(3) . ?
O7 C3 1.429(2) . ?
O7 C7 1.436(3) . ?
C1 C2 1.500(3) . ?
C2 C3 1.518(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.530(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.516(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.514(3) . ?
C5 H5A 0.9800 . ?
C6 C7 1.530(3) . ?
C6 H6A 0.9800 . ?
C7 C8 1.511(3) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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 109.17(17) . . ?
C5 O5 H5 109.5 . . ?
C6 O6 H6 109.5 . . ?
C3 O7 C7 113.05(15) . . ?
O1 C1 O4 120.5(2) . . ?
O1 C1 C2 129.2(2) . . ?
O4 C1 C2 110.34(19) . . ?
C1 C2 C3 104.10(18) . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 109.0 . . ?
O7 C3 C2 107.03(17) . . ?
O7 C3 C4 111.57(16) . . ?
C2 C3 C4 101.88(17) . . ?
O7 C3 H3 111.9 . . ?
C2 C3 H3 111.9 . . ?
C4 C3 H3 111.9 . . ?
O4 C4 C5 110.81(17) . . ?
O4 C4 C3 104.22(16) . . ?
C5 C4 C3 115.35(17) . . ?
O4 C4 H4 108.7 . . ?
C5 C4 H4 108.7 . . ?
C3 C4 H4 108.7 . . ?
O5 C5 C6 113.20(18) . . ?
O5 C5 C4 107.98(17) . . ?
C6 C5 C4 112.94(16) . . ?
O5 C5 H5A 107.5 . . ?
C6 C5 H5A 107.5 . . ?
C4 C5 H5A 107.5 . . ?
O6 C6 C5 105.69(16) . . ?
O6 C6 C7 111.74(17) . . ?
C5 C6 C7 109.03(17) . . ?
O6 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
C7 C6 H6A 110.1 . . ?
O7 C7 C8 107.14(18) . . ?
O7 C7 C6 107.06(17) . . ?
C8 C7 C6 114.30(19) . . ?
O7 C7 H7 109.4 . . ?
C8 C7 H7 109.4 . . ?
C6 C7 H7 109.4 . . ?
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 . . ?

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 168.50(19) . . . . ?
C4 O4 C1 C2 -10.3(2) . . . . ?
O1 C1 C2 C3 170.6(2) . . . . ?
O4 C1 C2 C3 -10.7(2) . . . . ?
C7 O7 C3 C2 166.75(17) . . . . ?
C7 O7 C3 C4 56.1(2) . . . . ?
C1 C2 C3 O7 -91.52(19) . . . . ?
C1 C2 C3 C4 25.7(2) . . . . ?
C1 O4 C4 C5 151.62(16) . . . . ?
C1 O4 C4 C3 26.9(2) . . . . ?
O7 C3 C4 O4 82.1(2) . . . . ?
C2 C3 C4 O4 -31.83(19) . . . . ?
O7 C3 C4 C5 -39.6(2) . . . . ?
C2 C3 C4 C5 -153.53(18) . . . . ?
O4 C4 C5 O5 46.0(2) . . . . ?
C3 C4 C5 O5 164.13(17) . . . . ?
O4 C4 C5 C6 -79.9(2) . . . . ?
C3 C4 C5 C6 38.2(2) . . . . ?
O5 C5 C6 O6 67.3(2) . . . . ?
C4 C5 C6 O6 -169.65(17) . . . . ?
O5 C5 C6 C7 -172.49(17) . . . . ?
C4 C5 C6 C7 -49.4(2) . . . . ?
C3 O7 C7 C8 168.13(19) . . . . ?
C3 O7 C7 C6 -68.8(2) . . . . ?
O6 C6 C7 O7 179.92(16) . . . . ?
C5 C6 C7 O7 63.5(2) . . . . ?
O6 C6 C7 C8 -61.6(2) . . . . ?
C5 C6 C7 C8 -178.06(19) . . . . ?

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 H5 O6 0.76 2.23 2.893(2) 146.9 2_646 yes
O6 H6 O1 0.83 2.12 2.911(2) 159.2 1_455 yes

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.039

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9
_database_code_depnum_ccdc_archive 'CCDC 2333778'
loop_
_audit_author_name
_audit_author_address
'Marko Rodic'
;University of Novi Sad
Serbia
;
_audit_update_record             
;
2024-02-19 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
#exp_code: data_SD8-134_2461_mP_222_abs_a  

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 3,6-Anhydro-2,8-dideoxy-D-glycero-L-gluco-octono-1,4-lactone 
;
_chemical_name_common            
; 3,6-Anhydro-2,8-dideoxy-D-glycero-L-gluco-octono-1,4-lactone 
;
_chemical_melting_point          397
_chemical_formula_moiety         'C8 H12 O5'
_chemical_formula_sum            'C8 H12 O5'
_chemical_formula_weight         188.18
_chemical_enantioexcess_bulk     1
_chemical_enantioexcess_bulk_technique OA
_chemical_optical_rotation       '[\a]^25^~D~ = +29.0 (c = 0.5, Me~2~CO)'
_chemical_absolute_configuration rmad

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.48541(5)
_cell_length_b                   10.62294(8)
_cell_length_c                   15.21442(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     886.561(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    10930
_cell_measurement_theta_min      2.8840
_cell_measurement_theta_max      71.8490

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.740
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.170
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.2046
-1 1 -2 0.2618
0 1 -1 0.0734
0 -1 1 0.0947
2 1 0 0.3444
-2 -1 -2 0.2999
-2 -1 0 0.3211
-1 -1 2 0.3110
0 -1 -1 0.1445
-1 2 -1 0.2629
-2 1 2 0.3379
0 0 -1 0.1524
0 0 1 0.2141
0 -1 -2 0.1500
1 1 2 0.3635
_exptl_absorpt_coefficient_mu    1.014
_shelx_estimated_absorpt_T_min   0.521
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.41.109a (Rigaku Oxford Diffraction, 2021) 
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) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_diffrn_ambient_temperature      295(2)
_diffrn_source                   
'fine-focus sealed X-ray tube (Oxford Diffraction)'
_diffrn_source_type              
'Enhance (Cu) X-ray Source (Oxford Diffraction)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Sapphire3 (Oxford Diffraction)'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00 108.00   1.00    3.00    --   36.41  19.00 120.00  101
  2  ω     22.00  90.00   1.00    3.00    --   36.41-125.00-150.00   68
  3  ω     20.00 104.00   1.00    3.00    --   36.41  57.00 120.00   84
  4  ω     22.00  90.00   1.00    3.00    --   36.41-125.00   0.00   68
  5  ω     39.00 106.00   1.00   12.00    --  108.00 -94.00-180.00   67
  6  ω    104.00 178.00   1.00   12.00    --  108.00 111.00 -90.00   74
  7  ω    101.00 176.00   1.00   12.00    --  108.00  77.00-120.00   75
  8  ω     41.00 126.00   1.00   12.00    --  108.00 -61.00-120.00   85
  9  ω     91.00 176.00   1.00   12.00    --  108.00  45.00  60.00   85
 10  ω     39.00 106.00   1.00   12.00    --  108.00 -94.00  60.00   67
 11  ω     39.00 106.00   1.00   12.00    --  108.00 -94.00 -90.00   67
 12  ω     39.00 106.00   1.00   12.00    --  108.00 -94.00  30.00   67
 13  ω     90.00 175.00   1.00   12.00    --  108.00  61.00-150.00   85
 14  ω     20.00 104.00   1.00    3.00    --   36.41  57.00-150.00   84
 15  ω    -31.00  53.00   1.00    3.00    --   36.41 -57.00  60.00   84
 16  ω     15.00 103.00   1.00    3.00    --   36.41  67.00 -86.00   88
 17  ω     20.00 104.00   1.00    3.00    --   36.41  57.00   0.00   84
 18  ω     91.00 176.00   1.00   12.00    --  108.00  45.00  30.00   85
 19  ω     90.00 175.00   1.00   12.00    --  108.00  61.00 -60.00   85
 20  ω     87.00 178.00   1.00   12.00    --  108.00  30.00 150.00   91
 21  ω     91.00 176.00   1.00   12.00    --  108.00  45.00-180.00   85
 22  ω     87.00 178.00   1.00   12.00    --  108.00  30.00   0.00   91
 23  ω     87.00 178.00   1.00   12.00    --  108.00  30.00 -90.00   91
 24  ω    101.00 176.00   1.00   12.00    --  108.00  77.00   0.00   75
 25  ω     91.00 176.00   1.00   12.00    --  108.00  52.00  95.00   85
 26  ω    -31.00  53.00   1.00    3.00    --   36.41 -57.00-180.00   84
 27  ω    -33.00  56.00   1.00    3.00    --   36.41 -37.00 120.00   89
 28  ω    -31.00  53.00   1.00    3.00    --   36.41 -57.00 -30.00   84
 29  ω     20.00 104.00   1.00    3.00    --   36.41  57.00  60.00   84
 30  ω     90.00 175.00   1.00   12.00    --  108.00  61.00-180.00   85
 31  ω    104.00 178.00   1.00   12.00    --  108.00 111.00 -30.00   74
 32  ω     90.00 175.00   1.00   12.00    --  108.00  61.00 150.00   85
 33  ω     91.00 176.00   1.00   12.00    --  108.00  45.00   0.00   85
 34  ω     87.00 178.00   1.00   12.00    --  108.00  30.00 -60.00   91
 35  ω     91.00 176.00   1.00   12.00    --  108.00  45.00 120.00   85
 36  ω     91.00 176.00   1.00   12.00    --  108.00  45.00  90.00   85
 37  ω     91.00 176.00   1.00   12.00    --  108.00  45.00-150.00   85
 38  ω     20.00  71.00   1.00    3.00    --   36.41  57.00 150.00   51
 39  ω      1.00  75.00   1.00    3.00    --   36.41 -99.00 -60.00   74
;
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1882033000
_diffrn_orient_matrix_UB_12      -0.0612880000
_diffrn_orient_matrix_UB_13      0.0617780000
_diffrn_orient_matrix_UB_21      -0.0985167000
_diffrn_orient_matrix_UB_22      0.1312231000
_diffrn_orient_matrix_UB_23      0.0244482000
_diffrn_orient_matrix_UB_31      -0.1836494000
_diffrn_orient_matrix_UB_32      -0.0075443000
_diffrn_orient_matrix_UB_33      -0.0764263000

_diffrn_reflns_number            13317
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.078
_diffrn_reflns_theta_max         71.945
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1726
_reflns_number_gt                1716
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'ShelXle (Hübschle et al., 2011)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+0.1071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   .
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.058(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 683 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_number_reflns         1726
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.5890(4) 0.29641(15) 0.40269(12) 0.0689(5) Uani 1 1 d . . . . .
O4 O 0.6893(3) 0.47190(13) 0.47251(9) 0.0437(4) Uani 1 1 d . . . . .
O5 O 0.5900(5) 0.73710(14) 0.61462(11) 0.0769(7) Uani 1 1 d . . . . .
H5A H 0.590(6) 0.753(3) 0.669(2) 0.077(9) Uiso 1 1 d . . . . .
O6 O 0.2774(3) 0.49263(14) 0.60126(9) 0.0483(4) Uani 1 1 d . . . . .
O7 O 0.4323(3) 0.31122(15) 0.71388(10) 0.0600(5) Uani 1 1 d . . . . .
H7A H 0.337(6) 0.291(3) 0.671(2) 0.078(9) Uiso 1 1 d . . . . .
C1 C 0.5261(4) 0.39247(18) 0.43675(12) 0.0435(5) Uani 1 1 d . . . . .
C2 C 0.2732(4) 0.4435(2) 0.44657(15) 0.0521(5) Uani 1 1 d . . . . .
H2A H 0.161350 0.378684 0.466386 0.063 Uiso 1 1 calc R U . . .
H2B H 0.214236 0.478152 0.391557 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3026(4) 0.54474(17) 0.51490(12) 0.0434(5) Uani 1 1 d . . . . .
H3 H 0.192073 0.615822 0.505034 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5678(4) 0.58250(17) 0.50715(12) 0.0431(5) Uani 1 1 d . . . . .
H4 H 0.589720 0.656063 0.469094 0.052 Uiso 1 1 calc R U . . .
C5 C 0.6477(4) 0.60848(17) 0.60095(12) 0.0471(5) Uani 1 1 d . . . . .
H5 H 0.821577 0.591426 0.609738 0.056 Uiso 1 1 calc R U . . .
C6 C 0.4865(3) 0.51995(16) 0.65490(11) 0.0388(4) Uani 1 1 d . . . . .
H6 H 0.432666 0.563899 0.708093 0.047 Uiso 1 1 calc R U . . .
C7 C 0.6096(4) 0.39696(18) 0.68126(12) 0.0410(4) Uani 1 1 d . . . . .
H7 H 0.689437 0.360132 0.629704 0.049 Uiso 1 1 calc R U . . .
C8 C 0.7961(4) 0.4161(3) 0.75301(16) 0.0610(6) Uani 1 1 d . . . . .
H8A H 0.859127 0.335971 0.771256 0.091 Uiso 1 1 calc R U . . .
H8B H 0.720858 0.457286 0.802192 0.091 Uiso 1 1 calc R U . . .
H8C H 0.927036 0.467328 0.731185 0.091 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 1.195(2) . ?
O4 C1 1.345(2) . ?
O4 C4 1.450(2) . ?
O5 C5 1.418(2) . ?
O5 H5A 0.84(3) . ?
O6 C3 1.432(2) . ?
O6 C6 1.437(2) . ?
O7 C7 1.422(2) . ?
O7 H7A 0.86(3) . ?
C1 C2 1.497(3) . ?
C2 C3 1.505(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.514(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.518(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.530(2) . ?
C5 H5 0.9800 . ?
C6 C7 1.524(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.510(3) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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 110.44(15) . . ?
C5 O5 H5A 109(2) . . ?
C3 O6 C6 111.46(15) . . ?
C7 O7 H7A 108(2) . . ?
O1 C1 O4 121.2(2) . . ?
O1 C1 C2 128.3(2) . . ?
O4 C1 C2 110.46(15) . . ?
C1 C2 C3 103.20(18) . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
O6 C3 C2 110.31(17) . . ?
O6 C3 C4 105.46(16) . . ?
C2 C3 C4 103.81(16) . . ?
O6 C3 H3 112.2 . . ?
C2 C3 H3 112.2 . . ?
C4 C3 H3 112.2 . . ?
O4 C4 C3 104.80(15) . . ?
O4 C4 C5 110.88(17) . . ?
C3 C4 C5 104.61(16) . . ?
O4 C4 H4 112.0 . . ?
C3 C4 H4 112.0 . . ?
C5 C4 H4 112.0 . . ?
O5 C5 C4 104.40(17) . . ?
O5 C5 C6 112.62(18) . . ?
C4 C5 C6 103.05(16) . . ?
O5 C5 H5 112.1 . . ?
C4 C5 H5 112.1 . . ?
C6 C5 H5 112.1 . . ?
O6 C6 C7 109.25(15) . . ?
O6 C6 C5 106.30(15) . . ?
C7 C6 C5 114.35(16) . . ?
O6 C6 H6 108.9 . . ?
C7 C6 H6 108.9 . . ?
C5 C6 H6 108.9 . . ?
O7 C7 C8 107.31(16) . . ?
O7 C7 C6 109.77(16) . . ?
C8 C7 C6 112.01(18) . . ?
O7 C7 H7 109.2 . . ?
C8 C7 H7 109.2 . . ?
C6 C7 H7 109.2 . . ?
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 . . ?

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 178.39(19) . . . . ?
C4 O4 C1 C2 -1.3(2) . . . . ?
O1 C1 C2 C3 164.8(2) . . . . ?
O4 C1 C2 C3 -15.5(2) . . . . ?
C6 O6 C3 C2 124.57(19) . . . . ?
C6 O6 C3 C4 13.07(19) . . . . ?
C1 C2 C3 O6 -87.6(2) . . . . ?
C1 C2 C3 C4 25.0(2) . . . . ?
C1 O4 C4 C3 17.58(18) . . . . ?
C1 O4 C4 C5 129.92(17) . . . . ?
O6 C3 C4 O4 89.79(16) . . . . ?
C2 C3 C4 O4 -26.24(19) . . . . ?
O6 C3 C4 C5 -26.94(18) . . . . ?
C2 C3 C4 C5 -142.97(18) . . . . ?
O4 C4 C5 O5 159.60(17) . . . . ?
C3 C4 C5 O5 -87.95(19) . . . . ?
O4 C4 C5 C6 -82.55(19) . . . . ?
C3 C4 C5 C6 29.90(19) . . . . ?
C3 O6 C6 C7 -117.77(16) . . . . ?
C3 O6 C6 C5 6.10(19) . . . . ?
O5 C5 C6 O6 89.5(2) . . . . ?
C4 C5 C6 O6 -22.5(2) . . . . ?
O5 C5 C6 C7 -149.92(18) . . . . ?
C4 C5 C6 C7 98.2(2) . . . . ?
O6 C6 C7 O7 -48.52(19) . . . . ?
C5 C6 C7 O7 -167.50(16) . . . . ?
O6 C6 C7 C8 -167.62(15) . . . . ?
C5 C6 C7 C8 73.4(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 0.84(3) 1.90(3) 2.728(2) 171(3) 3_656 yes
O7 H7A O1 0.86(3) 1.99(3) 2.828(2) 163(3) 4_456 yes

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.034

