# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_150824d_tw
_database_code_depnum_ccdc_archive 'CCDC 1989014'
_audit_update_record             
;
2020-03-09 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_publcif_datablock.id            {ddd6e317-8049-4c29-9476-8ea307472d64}

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H38 N2 O17 Y2'
_chemical_formula_weight         852.42

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'
N N 0.0061 0.0033 '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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3026(8)
_cell_length_b                   17.5625(14)
_cell_length_c                   11.3369(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.3500(10)
_cell_angle_gamma                90
_cell_volume                     1846.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1712
_cell_measurement_theta_min      2.494
_cell_measurement_theta_max      28.253

_exptl_crystal_description       bloc
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             868
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.199
_shelx_estimated_absorpt_T_min   0.681
_shelx_estimated_absorpt_T_max   0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6807
_exptl_absorpt_correction_T_max  0.7402
_exptl_absorpt_process_details   sadabs
_exptl_special_details           ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3171
_diffrn_reflns_av_unetI/netI     0.1804
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.143
_diffrn_reflns_theta_max         25.041
_diffrn_reflns_theta_full        25.041
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3171
_reflns_number_gt                1608
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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          
;
 Refined as a 2-component 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)+(0.0932P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3171
_refine_ls_number_parameters     240
_refine_ls_number_restraints     1030
_refine_ls_R_factor_all          0.1670
_refine_ls_R_factor_gt           0.0938
_refine_ls_wR_factor_ref         0.2286
_refine_ls_wR_factor_gt          0.2072
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      0.986
_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 0.51485(12) 0.10100(5) 0.93409(10) 0.0341(4) Uani 1 1 d . U . . .
N1 N 0.9147(14) 0.1829(8) 0.8317(12) 0.096(4) Uani 1 1 d D U . . .
O1 O 0.5621(9) 0.2351(4) 0.9874(7) 0.055(2) Uani 1 1 d D U . . .
O2 O 0.4114(8) 0.2103(4) 0.8316(6) 0.047(2) Uani 1 1 d D U . . .
O3 O 0.3220(11) 0.1347(5) 1.0531(8) 0.067(2) Uani 1 1 d D U . . .
O4 O 0.3873(9) 0.0181(4) 1.0796(7) 0.051(2) Uani 1 1 d D U . . .
O5 O 0.6607(9) 0.0877(4) 1.1061(7) 0.057(2) Uani 1 1 d D U . . .
O6 O 0.740(4) 0.1358(16) 0.868(2) 0.072(3) Uani 0.45(3) 1 d D U P A 1
O6' O 0.689(3) 0.1220(12) 0.825(2) 0.072(3) Uani 0.55(3) 1 d . U P A 2
O7 O 0.333(2) 0.1872(9) 0.5787(15) 0.080(5) Uani 0.5 1 d . U P . .
H7C H 0.255179 0.210061 0.556929 0.096 Uiso 0.5 1 d R U P . .
H7D H 0.370313 0.210455 0.639355 0.096 Uiso 0.5 1 d DR U P . .
O8 O 0.6651(9) -0.0351(4) 1.1747(7) 0.062(2) Uani 1 1 d D U . . .
O9 O 0.5192(18) 0.0770(8) 0.7126(9) 0.183(6) Uani 1 1 d . U . . .
H9B H 0.590303 0.102724 0.691516 0.220 Uiso 1 1 d DR U . . .
H9C H 0.443184 0.096584 0.679065 0.220 Uiso 1 1 d DR U . . .
C1 C 0.4716(12) 0.2569(5) 0.9011(8) 0.043(3) Uani 1 1 d D U . . .
C2 C 0.4411(12) 0.3402(5) 0.8877(9) 0.041(3) Uani 1 1 d D U . . .
C3 C 0.5005(11) 0.3943(5) 0.9666(8) 0.038(3) Uani 1 1 d D U . . .
H3 H 0.565355 0.378400 1.028124 0.045 Uiso 1 1 calc R U . . .
C4 C 0.4665(12) 0.4713(5) 0.9570(9) 0.037(3) Uani 1 1 d D U . . .
C5 C 0.3018(13) 0.0732(6) 1.1022(12) 0.062(4) Uani 1 1 d D U . . .
C6 C 0.216(5) 0.069(2) 1.209(3) 0.085(7) Uani 0.46(3) 1 d D U P B 1
H6A H 0.119515 0.086580 1.189047 0.128 Uiso 0.46(3) 1 calc R U P B 1
H6B H 0.260478 0.099633 1.271377 0.128 Uiso 0.46(3) 1 calc R U P B 1
H6C H 0.212261 0.016745 1.235553 0.128 Uiso 0.46(3) 1 calc R U P B 1
C6' C 0.154(2) 0.0517(19) 1.140(4) 0.085(7) Uani 0.54(3) 1 d D U P B 2
H6'1 H 0.105168 0.096648 1.163921 0.128 Uiso 0.54(3) 1 calc R U P B 2
H6'2 H 0.164906 0.016793 1.205444 0.128 Uiso 0.54(3) 1 calc R U P B 2
H6'3 H 0.098851 0.028025 1.075246 0.128 Uiso 0.54(3) 1 calc R U P B 2
C7 C 0.7056(13) 0.0334(5) 1.1797(10) 0.052(3) Uani 1 1 d D U . . .
C8 C 0.8725(13) 0.0074(6) 1.3601(10) 0.053(3) Uani 1 1 d D U . . .
H8 H 0.850511 -0.043968 1.350036 0.064 Uiso 1 1 calc R U . . .
C9 C 0.8426(12) 0.1354(5) 1.2923(9) 0.041(3) Uani 1 1 d D U . . .
H9 H 0.800105 0.170930 1.239789 0.049 Uiso 1 1 calc R U . . .
C11 C 0.959(2) 0.1393(13) 0.9405(15) 0.150(7) Uani 1 1 d D U . . .
H11A H 0.879718 0.108537 0.962070 0.226 Uiso 1 1 calc R U . . .
H11B H 0.986362 0.174017 1.003612 0.226 Uiso 1 1 calc R U . . .
H11C H 1.039140 0.107136 0.926139 0.226 Uiso 1 1 calc R U . . .
C12 C 1.0307(19) 0.2243(14) 0.7784(17) 0.155(9) Uani 1 1 d D U . . .
H12A H 1.037506 0.207007 0.698651 0.233 Uiso 1 1 calc DR U . . .
H12B H 1.120501 0.215106 0.823620 0.233 Uiso 1 1 calc R U . . .
H12C H 1.010071 0.277872 0.777974 0.233 Uiso 1 1 calc R U . . .
C13 C 0.7841(15) 0.1689(10) 0.7790(13) 0.103(4) Uani 1 1 d D U . . .
C14 C 0.752(2) 0.1962(12) 0.6546(15) 0.145(7) Uani 1 1 d D U . . .
H14A H 0.655273 0.215921 0.645780 0.218 Uiso 1 1 calc DR U . . .
H14B H 0.760633 0.154545 0.600860 0.218 Uiso 1 1 calc DR U . . .
H14C H 0.818580 0.235623 0.637601 0.218 Uiso 1 1 calc DR U . . .
C15 C 0.8103(13) 0.0589(5) 1.2782(9) 0.050(3) Uani 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
Y1 O6' 2.143(19) . ?
Y1 O4 2.291(7) 3_657 ?
Y1 O5 2.301(8) . ?
Y1 O8 2.313(7) 3_657 ?
Y1 O6 2.36(3) . ?
Y1 O3 2.399(9) . ?
Y1 O2 2.406(7) . ?
Y1 O1 2.462(8) . ?
Y1 O9 2.549(11) . ?
Y1 O4 2.558(8) . ?
Y1 Y1 3.867(2) 3_657 ?
N1 C13 1.335(9) . ?
N1 C12 1.469(9) . ?
N1 C11 1.483(9) . ?
O1 C1 1.299(8) . ?
O2 C1 1.239(8) . ?
O3 C5 1.235(8) . ?
O4 C5 1.290(8) . ?
O5 C7 1.314(8) . ?
O6 C13 1.263(10) . ?
O6' C13 1.34(3) . ?
O8 C7 1.261(8) . ?
C1 C2 1.496(8) . ?
C2 C3 1.390(8) . ?
C2 C9 1.430(13) 4_565 ?
C3 C4 1.392(8) . ?
C4 C8 1.402(13) 4_565 ?
C4 C4 1.504(18) 3_667 ?
C5 C6 1.506(10) . ?
C5 C6' 1.519(10) . ?
C7 C15 1.495(8) . ?
C8 C15 1.390(8) . ?
C9 C15 1.383(9) . ?
C13 C14 1.498(9) . ?

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
O6' Y1 O5 95.0(8) . . ?
O4 Y1 O5 75.7(3) 3_657 . ?
O4 Y1 O8 77.4(3) 3_657 3_657 ?
O5 Y1 O8 139.2(3) . 3_657 ?
O4 Y1 O6 81.3(7) 3_657 . ?
O5 Y1 O6 79.2(8) . . ?
O8 Y1 O6 125.9(9) 3_657 . ?
O6' Y1 O3 155.8(6) . . ?
O4 Y1 O3 125.5(3) 3_657 . ?
O5 Y1 O3 88.1(3) . . ?
O8 Y1 O3 83.2(3) 3_657 . ?
O6 Y1 O3 146.6(8) . . ?
O6' Y1 O2 82.8(6) . . ?
O4 Y1 O2 147.3(3) 3_657 . ?
O5 Y1 O2 132.7(2) . . ?
O8 Y1 O2 84.0(2) 3_657 . ?
O6 Y1 O2 88.5(6) . . ?
O3 Y1 O2 77.7(3) . . ?
O6' Y1 O1 81.3(7) . . ?
O4 Y1 O1 145.6(3) 3_657 . ?
O5 Y1 O1 78.8(2) . . ?
O8 Y1 O1 135.9(2) 3_657 . ?
O6 Y1 O1 71.5(8) . . ?
O3 Y1 O1 75.7(3) . . ?
O2 Y1 O1 54.1(2) . . ?
O6' Y1 O9 52.3(9) . . ?
O4 Y1 O9 75.3(4) 3_657 . ?
O5 Y1 O9 139.9(4) . . ?
O8 Y1 O9 57.1(4) 3_657 . ?
O6 Y1 O9 69.6(9) . . ?
O3 Y1 O9 131.5(4) . . ?
O2 Y1 O9 72.1(4) . . ?
O1 Y1 O9 112.6(4) . . ?
O6' Y1 O4 151.5(6) . . ?
O4 Y1 O4 74.4(3) 3_657 . ?
O5 Y1 O4 70.6(3) . . ?
O8 Y1 O4 72.9(3) 3_657 . ?
O6 Y1 O4 144.9(7) . . ?
O3 Y1 O4 51.3(3) . . ?
O2 Y1 O4 125.2(3) . . ?
O1 Y1 O4 117.9(3) . . ?
O9 Y1 O4 125.7(4) . . ?
O4 Y1 Y1 39.6(2) 3_657 3_657 ?
O5 Y1 Y1 68.55(18) . 3_657 ?
O8 Y1 Y1 71.15(18) 3_657 3_657 ?
O6 Y1 Y1 116.8(6) . 3_657 ?
O3 Y1 Y1 86.0(2) . 3_657 ?
O2 Y1 Y1 151.71(18) . 3_657 ?
O1 Y1 Y1 143.03(18) . 3_657 ?
O9 Y1 Y1 103.7(3) . 3_657 ?
O4 Y1 Y1 34.78(17) . 3_657 ?
C13 N1 C12 125.4(12) . . ?
C13 N1 C11 117.5(11) . . ?
C12 N1 C11 115.6(11) . . ?
C1 O1 Y1 90.2(5) . . ?
C1 O2 Y1 94.3(5) . . ?
C5 O3 Y1 100.6(7) . . ?
C5 O4 Y1 162.2(8) . 3_657 ?
C5 O4 Y1 91.4(6) . . ?
Y1 O4 Y1 105.7(3) 3_657 . ?
C7 O5 Y1 138.6(6) . . ?
C13 O6 Y1 136(2) . . ?
C13 O6' Y1 151.4(19) . . ?
C7 O8 Y1 134.7(6) . 3_657 ?
O2 C1 O1 121.3(8) . . ?
O2 C1 C2 120.6(7) . . ?
O1 C1 C2 118.1(7) . . ?
C3 C2 C9 118.8(8) . 4_565 ?
C3 C2 C1 122.7(8) . . ?
C9 C2 C1 118.4(7) 4_565 . ?
C2 C3 C4 122.5(8) . . ?
C3 C4 C8 116.4(8) . 4_565 ?
C3 C4 C4 121.4(10) . 3_667 ?
C8 C4 C4 122.2(10) 4_565 3_667 ?
O3 C5 O4 116.7(10) . . ?
O3 C5 C6 121.2(17) . . ?
O4 C5 C6 119.5(17) . . ?
O3 C5 C6' 121.1(16) . . ?
O4 C5 C6' 117.0(15) . . ?
O8 C7 O5 125.7(8) . . ?
O8 C7 C15 119.7(8) . . ?
O5 C7 C15 114.5(7) . . ?
C15 C8 C4 123.5(9) . 4_666 ?
C15 C9 C2 120.0(8) . 4_666 ?
O6 C13 N1 93.8(19) . . ?
N1 C13 O6' 123.2(17) . . ?
O6 C13 C14 148(2) . . ?
N1 C13 C14 118.2(14) . . ?
O6' C13 C14 117.8(17) . . ?
C9 C15 C8 118.7(9) . . ?
C9 C15 C7 120.1(8) . . ?
C8 C15 C7 121.2(9) . . ?

_refine_diff_density_max         1.445
_refine_diff_density_min         -1.117
_refine_diff_density_rms         0.181


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
