# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_ay-cas13429-83-9-100k_auto
_database_code_depnum_ccdc_archive 'CCDC 2108436'
loop_
_audit_author_name
_audit_author_address
'Yong Ai'
;Nanchang University
China
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 O4'
_chemical_formula_sum            'C10 H14 O4'
_chemical_formula_weight         198.21

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           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                   6.29835(9)
_cell_length_b                   10.64131(14)
_cell_length_c                   7.53892(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.5036(14)
_cell_angle_gamma                90
_cell_volume                     491.310(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2412
_cell_measurement_theta_min      7.2300
_cell_measurement_theta_max      75.6200

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.865
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2534
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_av_R_equivalents  0.0102
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         7.232
_diffrn_reflns_theta_max         75.825
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.672
_diffrn_reflns_point_group_measured_fraction_full 0.721
_reflns_number_total             1379
_reflns_number_gt                1376
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.365
_reflns_Friedel_fraction_max     0.381
_reflns_Friedel_fraction_full    0.423

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+0.0798P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 367 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(7)
_chemical_absolute_configuration .
_refine_ls_number_reflns         1379
_refine_ls_number_parameters     132
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0587
_refine_ls_wR_factor_gt          0.0586
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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
O11 O -0.34369(18) -0.89782(12) -0.09277(13) 0.0204(3) Uani 1 1 d . . . . .
O6 O -0.44218(16) -1.00536(11) -0.35470(13) 0.0157(3) Uani 1 1 d . . . . .
O10 O -0.40081(18) -1.22117(12) -0.70658(14) 0.0197(3) Uani 1 1 d . . . . .
H10 H -0.487147 -1.272048 -0.771779 0.030 Uiso 1 1 calc R U . . .
O9 O -0.68697(18) -1.18112(13) -0.58390(15) 0.0240(3) Uani 1 1 d . . . . .
C1 C -0.3310(2) -1.10033(15) -0.4416(2) 0.0142(3) Uani 1 1 d . . . . .
C3 C 0.0113(2) -1.00150(18) -0.31179(19) 0.0181(3) Uani 1 1 d . . . . .
H3A H 0.029950 -0.909908 -0.290756 0.022 Uiso 1 1 calc R U . . .
H3B H 0.156174 -1.040168 -0.303927 0.022 Uiso 1 1 calc R U . . .
C13 C -0.0552(3) -1.27705(16) -0.3203(2) 0.0178(3) Uani 1 1 d . . . . .
H13A H -0.137048 -1.345422 -0.392580 0.027 Uiso 1 1 calc R U . . .
H13B H 0.035141 -1.311144 -0.206824 0.027 Uiso 1 1 calc R U . . .
H13C H 0.038546 -1.236380 -0.390324 0.027 Uiso 1 1 calc R U . . .
C5 C -0.3041(2) -0.97983(15) -0.19179(19) 0.0160(3) Uani 1 1 d . . . . .
C4 C -0.1057(2) -1.06271(16) -0.17224(19) 0.0153(3) Uani 1 1 d . . . . .
C12 C 0.0316(3) -1.07914(17) 0.0200(2) 0.0215(4) Uani 1 1 d . . . . .
H12A H 0.155159 -1.134646 0.018010 0.032 Uiso 1 1 calc R U . . .
H12B H -0.057795 -1.116322 0.096740 0.032 Uiso 1 1 calc R U . . .
H12C H 0.086195 -0.997091 0.069552 0.032 Uiso 1 1 calc R U . . .
C2 C -0.1465(2) -1.02933(16) -0.49934(19) 0.0166(3) Uani 1 1 d . . . . .
H2A H -0.200228 -0.950799 -0.565097 0.020 Uiso 1 1 calc R U . . .
H2B H -0.075677 -1.082054 -0.577130 0.020 Uiso 1 1 calc R U . . .
C8 C -0.4967(2) -1.16966(16) -0.58493(18) 0.0155(3) Uani 1 1 d . . . . .
C7 C -0.2140(2) -1.18124(15) -0.27574(19) 0.0140(3) Uani 1 1 d . . . . .
C14 C -0.3723(3) -1.24696(17) -0.1790(2) 0.0187(3) Uani 1 1 d . . . . .
H14A H -0.476864 -1.185535 -0.152852 0.028 Uiso 1 1 calc R U . . .
H14B H -0.290020 -1.284041 -0.064532 0.028 Uiso 1 1 calc R U . . .
H14C H -0.451169 -1.313280 -0.257897 0.028 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
O11 C5 1.212(2) . ?
O6 C5 1.3564(17) . ?
O6 C1 1.4680(18) . ?
O10 C8 1.3286(19) . ?
O9 C8 1.2064(19) . ?
C1 C8 1.508(2) . ?
C1 C2 1.532(2) . ?
C1 C7 1.555(2) . ?
C3 C2 1.5553(19) . ?
C3 C4 1.561(2) . ?
C13 C7 1.520(2) . ?
C5 C4 1.508(2) . ?
C4 C12 1.5142(19) . ?
C4 C7 1.554(2) . ?
C7 C14 1.534(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
C5 O6 C1 105.67(11) . . ?
O6 C1 C8 109.52(12) . . ?
O6 C1 C2 105.05(13) . . ?
C8 C1 C2 118.79(12) . . ?
O6 C1 C7 102.01(11) . . ?
C8 C1 C7 115.09(14) . . ?
C2 C1 C7 104.67(12) . . ?
C2 C3 C4 103.36(12) . . ?
O11 C5 O6 121.42(14) . . ?
O11 C5 C4 130.25(14) . . ?
O6 C5 C4 108.23(12) . . ?
C5 C4 C12 115.85(12) . . ?
C5 C4 C7 99.74(12) . . ?
C12 C4 C7 118.18(14) . . ?
C5 C4 C3 101.58(12) . . ?
C12 C4 C3 116.04(13) . . ?
C7 C4 C3 102.78(11) . . ?
C1 C2 C3 101.64(11) . . ?
O9 C8 O10 125.11(15) . . ?
O9 C8 C1 124.55(14) . . ?
O10 C8 C1 110.27(12) . . ?
C13 C7 C14 109.48(14) . . ?
C13 C7 C4 114.91(12) . . ?
C14 C7 C4 112.89(12) . . ?
C13 C7 C1 113.98(11) . . ?
C14 C7 C1 113.33(12) . . ?
C4 C7 C1 91.40(12) . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.029



####################################################################### 
# 
# 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_ay-cas13429-83-9-373k_auto
_database_code_depnum_ccdc_archive 'CCDC 2108441'
loop_
_audit_author_name
_audit_author_address
'Yong Ai'
;Nanchang University
China
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H14 O4'
_chemical_formula_sum            'C10 H14 O4'
_chemical_formula_weight         198.21
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N H O '
_chemical_oxdiff_usercomment     'C H N O'
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'
N N 0.0311 0.0180 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.3879(2)
_cell_length_b                   10.8484(3)
_cell_length_c                   7.6137(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.203(3)
_cell_angle_gamma                90
_cell_volume                     513.67(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2383
_cell_measurement_temperature    373.01(11)
_cell_measurement_theta_max      75.6100
_cell_measurement_theta_min      4.0090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             212
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2651
_diffrn_reflns_point_group_measured_fraction_full 0.656
_diffrn_reflns_point_group_measured_fraction_max 0.607
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.755
_diffrn_reflns_theta_min         7.121
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      373.01(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  18.00   0.50    0.05    --   45.15 -37.00-150.00   92
  2  ω     37.00  62.00   0.50    0.20    --  107.00 -61.00-180.00   50
  3  ω      1.00  26.00   0.50    0.05    --   45.15 -25.00-104.00   50
  4  ω     35.00  66.00   0.50    0.20    --  107.00 -61.00 -30.00   62
  5  ω     49.00  84.00   0.50    0.05    --   45.15  25.00  59.00   70
  6  ω     38.00  67.00   0.50    0.20    --  107.00 -61.00 120.00   58
  7  ω    100.00 164.00   0.50    0.20    --  107.00  25.00  59.00  128
  8  ω   -107.00 -71.00   0.50    0.20    -- -102.00 125.00 150.00   72
  9  ω    -68.00 -34.00   0.50    0.20    -- -102.00 125.00 150.00   68
 10  ω    -64.00 -34.00   0.50    0.05    --  -45.15 -25.00-104.00   60
 11  ω   -108.00 -73.00   0.50    0.05    --  -45.15 -25.00-104.00   70
 12  ω   -120.00 -93.00   0.50    0.20    -- -102.00 -25.00-104.00   54
 13  ω   -175.00-144.00   0.50    0.20    -- -102.00 -15.00 -30.00   62
 14  ω   -119.00 -87.00   0.50    0.20    -- -102.00 -15.00 -30.00   64
 15  ω    -98.00 -67.00   0.50    0.20    -- -102.00  77.00 -90.00   62
 16  ω    -53.00 -28.00   0.50    0.20    -- -102.00  77.00 -90.00   50
 17  ω    -59.00 -29.00   0.50    0.20    -- -102.00  61.00   0.00   60
 18  ω    -60.00 -34.00   0.50    0.20    -- -102.00  61.00 -30.00   52
 19  ω    -53.00 -28.00   0.50    0.20    -- -102.00  61.00-120.00   50
 20  ω    -68.00 -32.00   0.50    0.20    -- -102.00  61.00-180.00   72
 21  ω    -39.00  27.00   0.50    0.05    --  -45.15  37.00-180.00  132
 22  ω    -69.00 -28.00   0.50    0.20    -- -102.00  61.00  60.00   82
 23  ω    -68.00 -29.00   0.50    0.20    -- -102.00  61.00 120.00   78
 24  ω    -64.00 -30.00   0.50    0.20    -- -102.00  61.00 150.00   68
 25  ω    -28.00  31.00   0.50    0.05    --  -45.15  25.00  59.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0735755000
_diffrn_orient_matrix_UB_12      0.0475965000
_diffrn_orient_matrix_UB_13      -0.1667974000
_diffrn_orient_matrix_UB_21      0.2363779000
_diffrn_orient_matrix_UB_22      -0.0195190000
_diffrn_orient_matrix_UB_23      0.0990169000
_diffrn_orient_matrix_UB_31      -0.0084305000
_diffrn_orient_matrix_UB_32      -0.1323836000
_diffrn_orient_matrix_UB_33      -0.0745893000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.270
_reflns_Friedel_fraction_full    0.310
_reflns_Friedel_fraction_max     0.272
_reflns_number_gt                1261
_reflns_number_total             1299
_reflns_odcompleteness_completeness 96.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.416
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1299
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.416
_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)+(0.1777P)²+0.1069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2882
_refine_ls_wR_factor_ref         0.2892
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00C(H00F,H00G)
2.b Idealised Me refined as rotating group:
 C00B(H00C,H00D,H00E), C00D(H00H,H00I,H00J), C00E(H00K,H00L,H00M)
2.c Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O -0.4402(6) -0.4214(4) -0.3571(6) 0.0552(11) Uani 1 1 d . . . . .
O002 O -0.3979(8) -0.6382(6) -0.6986(7) 0.0722(15) Uani 1 1 d . . . . .
H002 H -0.482110 -0.687038 -0.759921 0.108 Uiso 1 1 calc R U . . .
O003 O -0.3490(10) -0.3143(6) -0.1022(7) 0.0776(17) Uani 1 1 d . . . . .
O004 O -0.6793(8) -0.5909(9) -0.5865(8) 0.093(2) Uani 1 1 d . . . . .
C005 C -0.3064(11) -0.3946(6) -0.1977(9) 0.0560(15) Uani 1 1 d . . . . .
C006 C -0.2140(8) -0.5915(6) -0.2782(7) 0.0466(13) Uani 1 1 d . . . . .
C007 C -0.4921(9) -0.5831(7) -0.5827(8) 0.0542(15) Uani 1 1 d . . . . .
C008 C -0.1102(9) -0.4744(6) -0.1785(8) 0.0521(14) Uani 1 1 d . . . . .
C009 C -0.3300(8) -0.5146(6) -0.4432(7) 0.0440(13) Uani 1 1 d . . . . .
C00A C -0.1488(10) -0.4450(7) -0.5001(8) 0.0575(16) Uani 1 1 d . . . . .
H00A H -0.201448 -0.370375 -0.565779 0.069 Uiso 1 1 calc R U . . .
H00B H -0.078560 -0.496020 -0.574075 0.069 Uiso 1 1 calc R U . . .
C00B C -0.0546(13) -0.6857(7) -0.3175(10) 0.0632(17) Uani 1 1 d . . . . .
H00C H 0.034578 -0.714432 -0.206003 0.095 Uiso 1 1 calc R U . . .
H00D H 0.033733 -0.648078 -0.389076 0.095 Uiso 1 1 calc R U . . .
H00E H -0.131274 -0.753940 -0.382264 0.095 Uiso 1 1 calc R U . . .
C00C C 0.0036(10) -0.4151(8) -0.3175(9) 0.0626(17) Uani 1 1 d . . . . .
H00F H 0.019097 -0.326784 -0.299296 0.075 Uiso 1 1 calc R U . . .
H00G H 0.144470 -0.451189 -0.309254 0.075 Uiso 1 1 calc R U . . .
C00D C -0.3696(14) -0.6562(8) -0.1810(11) 0.0683(19) Uani 1 1 d . . . . .
H00H H -0.462119 -0.596130 -0.145316 0.102 Uiso 1 1 calc R U . . .
H00I H -0.288937 -0.698024 -0.075986 0.102 Uiso 1 1 calc R U . . .
H00J H -0.454864 -0.714984 -0.260892 0.102 Uiso 1 1 calc R U . . .
C00E C 0.0253(15) -0.4871(10) 0.0125(11) 0.083(2) Uani 1 1 d . . . . .
H00K H -0.056313 -0.528763 0.085907 0.124 Uiso 1 1 calc R U . . .
H00L H 0.065318 -0.406686 0.061578 0.124 Uiso 1 1 calc R U . . .
H00M H 0.152501 -0.533733 0.010800 0.124 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
O001 C005 1.347(8) . ?
O001 C009 1.469(7) . ?
O002 H002 0.8200 . ?
O002 C007 1.320(8) . ?
O003 C005 1.205(8) . ?
O004 C007 1.192(8) . ?
C005 C008 1.503(8) . ?
C006 C008 1.549(9) . ?
C006 C009 1.548(8) . ?
C006 C00B 1.519(8) . ?
C006 C00D 1.538(8) . ?
C007 C009 1.500(8) . ?
C008 C00C 1.554(9) . ?
C008 C00E 1.519(9) . ?
C009 C00A 1.526(7) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A C00C 1.539(9) . ?
C00B H00C 0.9600 . ?
C00B H00D 0.9600 . ?
C00B H00E 0.9600 . ?
C00C H00F 0.9700 . ?
C00C H00G 0.9700 . ?
C00D H00H 0.9600 . ?
C00D H00I 0.9600 . ?
C00D H00J 0.9600 . ?
C00E H00K 0.9600 . ?
C00E H00L 0.9600 . ?
C00E H00M 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
C005 O001 C009 106.3(4) . . ?
C007 O002 H002 109.5 . . ?
O001 C005 C008 107.9(5) . . ?
O003 C005 O001 121.1(6) . . ?
O003 C005 C008 131.0(7) . . ?
C009 C006 C008 91.6(4) . . ?
C00B C006 C008 114.6(5) . . ?
C00B C006 C009 114.9(5) . . ?
C00B C006 C00D 108.9(6) . . ?
C00D C006 C008 112.9(5) . . ?
C00D C006 C009 113.2(5) . . ?
O002 C007 C009 110.6(5) . . ?
O004 C007 O002 124.0(6) . . ?
O004 C007 C009 125.4(6) . . ?
C005 C008 C006 99.8(5) . . ?
C005 C008 C00C 101.8(5) . . ?
C005 C008 C00E 115.2(6) . . ?
C006 C008 C00C 102.7(5) . . ?
C00E C008 C006 118.8(6) . . ?
C00E C008 C00C 115.9(6) . . ?
O001 C009 C006 101.4(4) . . ?
O001 C009 C007 109.5(5) . . ?
O001 C009 C00A 104.9(5) . . ?
C007 C009 C006 115.6(6) . . ?
C007 C009 C00A 119.4(4) . . ?
C00A C009 C006 104.1(4) . . ?
C009 C00A H00A 111.3 . . ?
C009 C00A H00B 111.3 . . ?
C009 C00A C00C 102.3(4) . . ?
H00A C00A H00B 109.2 . . ?
C00C C00A H00A 111.3 . . ?
C00C C00A H00B 111.3 . . ?
C006 C00B H00C 109.5 . . ?
C006 C00B H00D 109.5 . . ?
C006 C00B H00E 109.5 . . ?
H00C C00B H00D 109.5 . . ?
H00C C00B H00E 109.5 . . ?
H00D C00B H00E 109.5 . . ?
C008 C00C H00F 111.1 . . ?
C008 C00C H00G 111.1 . . ?
C00A C00C C008 103.3(5) . . ?
C00A C00C H00F 111.1 . . ?
C00A C00C H00G 111.1 . . ?
H00F C00C H00G 109.1 . . ?
C006 C00D H00H 109.5 . . ?
C006 C00D H00I 109.5 . . ?
C006 C00D H00J 109.5 . . ?
H00H C00D H00I 109.5 . . ?
H00H C00D H00J 109.5 . . ?
H00I C00D H00J 109.5 . . ?
C008 C00E H00K 109.5 . . ?
C008 C00E H00L 109.5 . . ?
C008 C00E H00M 109.5 . . ?
H00K C00E H00L 109.5 . . ?
H00K C00E H00M 109.5 . . ?
H00L C00E H00M 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.432
_oxdiff_exptl_absorpt_empirical_full_min 0.595
