# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 2085515'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2021-05-24 deposited with the CCDC.	2021-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H19 O11 Y'
_chemical_formula_sum            'C9 H19 O11 Y'
_chemical_formula_weight         392.15

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'
Y Y -2.7962 3.5667 '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                   10.5780(8)
_cell_length_b                   5.7390(5)
_cell_length_c                   13.2053(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.765(3)
_cell_angle_gamma                90
_cell_volume                     794.31(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5848
_cell_measurement_theta_min      2.320
_cell_measurement_theta_max      30.482

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   0.6105
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    3.720
_shelx_estimated_absorpt_T_min   0.457
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8780
_diffrn_reflns_av_unetI/netI     0.0805
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.943
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3457
_reflns_number_gt                3175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_max     0.956
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 4-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0048P)²+9.8911P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1141 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(6)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3457
_refine_ls_number_parameters     190
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.121
_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
Y1 Y 0.26411(9) 0.50818(2) 0.65048(8) 0.0119(2) Uani 1 1 d . . . . .
O1 O 0.1933(8) 0.1963(18) 0.5457(7) 0.018(2) Uani 1 1 d . . . . .
H1 H 0.172203 0.079740 0.579384 0.027 Uiso 1 1 d R U . . .
H2 H 0.238393 0.142699 0.502394 0.027 Uiso 1 1 d R U . . .
O2 O 0.2436(8) 0.6277(17) 0.4774(6) 0.0176(19) Uani 1 1 d . . . . .
H3 H 0.186616 0.585436 0.429298 0.026 Uiso 1 1 d R U . . .
H4 H 0.273326 0.753016 0.455718 0.026 Uiso 1 1 d R U . . .
O11 O 0.4675(9) 0.4211(17) 0.6203(7) 0.020(2) Uani 1 1 d . . . . .
O12 O 0.6634(7) 0.524(3) 0.5918(6) 0.0181(18) Uani 1 1 d . . . . .
O13 O 0.3940(7) 0.8351(17) 0.6507(7) 0.0153(18) Uani 1 1 d . . . . .
H13 H 0.370086 0.949522 0.684209 0.023 Uiso 1 1 d R U . . .
O21 O 0.3198(9) 0.1905(17) 0.7553(7) 0.018(2) Uani 1 1 d . . . . .
O22 O 0.3713(9) 0.020(3) 0.9058(6) 0.033(2) Uani 1 1 d . . . . .
O23 O 0.3163(9) 0.5971(17) 0.8264(7) 0.022(2) Uani 1 1 d . . . . .
H23 H 0.333660 0.731481 0.851559 0.032 Uiso 1 1 d R U . . .
O31 O 0.1261(8) 0.8224(17) 0.6526(8) 0.021(2) Uani 1 1 d . . . . .
O32 O -0.0535(7) 0.988(2) 0.6838(6) 0.0168(18) Uani 1 1 d . . . . .
O33 O 0.0594(9) 0.4132(18) 0.6966(8) 0.024(2) Uani 1 1 d . . . . .
H33 H 0.024145 0.279855 0.692606 0.036 Uiso 1 1 d R U . . .
C11 C 0.5601(11) 0.569(2) 0.6184(9) 0.0149(19) Uani 1 1 d . U . . .
C12 C 0.5267(11) 0.821(2) 0.6406(10) 0.0149(19) Uani 1 1 d . . . . .
H12 H 0.542603 0.918664 0.580950 0.018 Uiso 1 1 calc R U . . .
C13 C 0.6104(11) 0.907(3) 0.7327(10) 0.023(3) Uani 1 1 d . . . . .
H13A H 0.699685 0.901146 0.720412 0.034 Uiso 1 1 calc R U . . .
H13B H 0.599341 0.808073 0.791451 0.034 Uiso 1 1 calc R U . . .
H13C H 0.587372 1.067714 0.746984 0.034 Uiso 1 1 calc R U . . .
C21 C 0.3489(12) 0.191(2) 0.8513(10) 0.018(3) Uani 1 1 d . . . . .
C22 C 0.3559(14) 0.428(3) 0.9037(10) 0.026(3) Uani 1 1 d . . . . .
H22 H 0.446656 0.459593 0.932386 0.031 Uiso 1 1 calc R U . . .
C23 C 0.2751(17) 0.439(4) 0.9896(11) 0.045(5) Uani 1 1 d . . . . .
H23A H 0.283343 0.292761 1.028164 0.068 Uiso 1 1 calc R U . . .
H23B H 0.185574 0.463053 0.961121 0.068 Uiso 1 1 calc R U . . .
H23C H 0.303884 0.568856 1.035202 0.068 Uiso 1 1 calc R U . . .
C31 C 0.0173(12) 0.818(2) 0.6808(10) 0.017(3) Uani 1 1 d . . . . .
C32 C -0.0337(12) 0.579(3) 0.7097(12) 0.025(3) Uani 1 1 d . . . . .
H32 H -0.115390 0.542115 0.665227 0.030 Uiso 1 1 calc R U . . .
C33 C -0.0546(17) 0.585(3) 0.8220(12) 0.039(4) Uani 1 1 d . . . . .
H33A H -0.083202 0.431375 0.842043 0.058 Uiso 1 1 calc R U . . .
H33B H -0.119530 0.701787 0.831458 0.058 Uiso 1 1 calc R U . . .
H33C H 0.025673 0.625330 0.864512 0.058 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
Y1 O11 2.296(9) . ?
Y1 O21 2.316(9) . ?
Y1 O31 2.323(9) . ?
Y1 O1 2.324(9) . ?
Y1 O13 2.325(9) . ?
Y1 O2 2.368(8) . ?
Y1 O23 2.369(9) . ?
Y1 O33 2.390(9) . ?
O1 H1 0.8500 . ?
O1 H2 0.8500 . ?
O2 H3 0.8500 . ?
O2 H4 0.8500 . ?
O11 C11 1.299(14) . ?
O12 C11 1.220(13) . ?
O13 C12 1.430(13) . ?
O13 H13 0.8500 . ?
O21 C21 1.265(15) . ?
O22 C21 1.22(2) . ?
O23 C22 1.431(16) . ?
O23 H23 0.8500 . ?
O31 C31 1.256(15) . ?
O32 C31 1.236(18) . ?
O33 C32 1.399(16) . ?
O33 H33 0.8500 . ?
C11 C12 1.525(17) . ?
C12 C13 1.489(18) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 C22 1.52(2) . ?
C22 C23 1.51(2) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C31 C32 1.537(19) . ?
C32 C33 1.53(2) . ?
C32 H32 1.0000 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

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
O11 Y1 O21 76.3(3) . . ?
O11 Y1 O31 140.9(3) . . ?
O21 Y1 O31 135.5(3) . . ?
O11 Y1 O1 87.9(3) . . ?
O21 Y1 O1 77.6(3) . . ?
O31 Y1 O1 116.9(3) . . ?
O11 Y1 O13 66.9(3) . . ?
O21 Y1 O13 122.1(3) . . ?
O31 Y1 O13 75.3(3) . . ?
O1 Y1 O13 139.9(3) . . ?
O11 Y1 O2 82.0(3) . . ?
O21 Y1 O2 141.9(3) . . ?
O31 Y1 O2 79.1(3) . . ?
O1 Y1 O2 70.6(3) . . ?
O13 Y1 O2 75.2(3) . . ?
O11 Y1 O23 96.7(3) . . ?
O21 Y1 O23 65.0(3) . . ?
O31 Y1 O23 83.4(3) . . ?
O1 Y1 O23 139.8(3) . . ?
O13 Y1 O23 76.5(3) . . ?
O2 Y1 O23 149.6(3) . . ?
O11 Y1 O33 153.8(3) . . ?
O21 Y1 O33 80.5(3) . . ?
O31 Y1 O33 65.3(3) . . ?
O1 Y1 O33 75.3(3) . . ?
O13 Y1 O33 137.7(3) . . ?
O2 Y1 O33 110.1(3) . . ?
O23 Y1 O33 84.2(3) . . ?
Y1 O1 H1 112.4 . . ?
Y1 O1 H2 120.9 . . ?
H1 O1 H2 106.1 . . ?
Y1 O2 H3 127.0 . . ?
Y1 O2 H4 125.5 . . ?
H3 O2 H4 104.3 . . ?
C11 O11 Y1 126.0(8) . . ?
C12 O13 Y1 122.8(8) . . ?
C12 O13 H13 117.3 . . ?
Y1 O13 H13 114.0 . . ?
C21 O21 Y1 127.3(9) . . ?
C22 O23 Y1 124.1(8) . . ?
C22 O23 H23 108.0 . . ?
Y1 O23 H23 126.1 . . ?
C31 O31 Y1 126.1(9) . . ?
C32 O33 Y1 123.6(8) . . ?
C32 O33 H33 108.1 . . ?
Y1 O33 H33 126.5 . . ?
O12 C11 O11 125.1(13) . . ?
O12 C11 C12 119.7(12) . . ?
O11 C11 C12 114.9(10) . . ?
O13 C12 C13 112.8(10) . . ?
O13 C12 C11 109.2(10) . . ?
C13 C12 C11 110.1(11) . . ?
O13 C12 H12 108.2 . . ?
C13 C12 H12 108.2 . . ?
C11 C12 H12 108.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O22 C21 O21 126.3(14) . . ?
O22 C21 C22 117.1(12) . . ?
O21 C21 C22 116.5(12) . . ?
O23 C22 C23 111.4(13) . . ?
O23 C22 C21 106.9(10) . . ?
C23 C22 C21 112.4(13) . . ?
O23 C22 H22 108.7 . . ?
C23 C22 H22 108.7 . . ?
C21 C22 H22 108.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O32 C31 O31 125.1(13) . . ?
O32 C31 C32 117.5(11) . . ?
O31 C31 C32 117.4(12) . . ?
O33 C32 C33 109.3(12) . . ?
O33 C32 C31 107.4(10) . . ?
C33 C32 C31 108.9(13) . . ?
O33 C32 H32 110.4 . . ?
C33 C32 H32 110.4 . . ?
C31 C32 H32 110.4 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
Y1 O11 C11 O12 -171.9(9) . . . . ?
Y1 O11 C11 C12 1.2(15) . . . . ?
Y1 O13 C12 C13 -116.4(11) . . . . ?
Y1 O13 C12 C11 6.3(13) . . . . ?
O12 C11 C12 O13 168.9(11) . . . . ?
O11 C11 C12 O13 -4.6(15) . . . . ?
O12 C11 C12 C13 -66.7(15) . . . . ?
O11 C11 C12 C13 119.7(12) . . . . ?
Y1 O21 C21 O22 175.8(10) . . . . ?
Y1 O21 C21 C22 -3.9(17) . . . . ?
Y1 O23 C22 C23 -126.6(11) . . . . ?
Y1 O23 C22 C21 -3.4(14) . . . . ?
O22 C21 C22 O23 -175.4(11) . . . . ?
O21 C21 C22 O23 4.3(16) . . . . ?
O22 C21 C22 C23 -52.8(17) . . . . ?
O21 C21 C22 C23 126.9(14) . . . . ?
Y1 O31 C31 O32 178.0(9) . . . . ?
Y1 O31 C31 C32 -4.5(17) . . . . ?
Y1 O33 C32 C33 -113.5(11) . . . . ?
Y1 O33 C32 C31 4.5(15) . . . . ?
O32 C31 C32 O33 177.5(11) . . . . ?
O31 C31 C32 O33 -0.2(17) . . . . ?
O32 C31 C32 C33 -64.2(16) . . . . ?
O31 C31 C32 C33 118.1(14) . . . . ?

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
O1 H2 O12 0.85 1.85 2.704(13) 179.7 2_646
O1 H1 O31 0.85 1.87 2.716(14) 179.6 1_545
O2 H4 O12 0.85 1.84 2.687(16) 179.6 2_656
O2 H3 O32 0.85 1.99 2.839(12) 179.7 2_546
O13 H13 O21 0.85 1.79 2.642(13) 179.8 1_565
O23 H23 O22 0.85 1.83 2.677(19) 179.9 1_565
O33 H33 O32 0.85 1.86 2.712(16) 179.9 1_545

_refine_diff_density_max         2.148
_refine_diff_density_min         -1.853
_refine_diff_density_rms         0.162

