# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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 1455859'
_audit_update_record             
;
2016-02-25 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            DDL-JE10_55
_chemical_formula_moiety         'C15 H12 Er O9 S3'
_chemical_formula_sum            'C15 H12 Er O9 S3'
_chemical_formula_iupac          ?
_chemical_formula_weight         599.69

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7389(5)
_cell_length_b                   9.6787(6)
_cell_length_c                   13.1985(8)
_cell_angle_alpha                81.999(2)
_cell_angle_beta                 75.0000(10)
_cell_angle_gamma                75.514(2)
_cell_volume                     921.62(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9992
_cell_measurement_theta_min      2.8797
_cell_measurement_theta_max      28.3518
_cell_measurement_temperature    298.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    2.161
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580

_exptl_absorpt_coefficient_mu    4.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      298.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker AXS'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            13358
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_full        28.35
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             4584
_reflns_number_gt                4181
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0607
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_number_reflns         4584
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0259P)²+0.9323P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.099
_refine_diff_density_min         -0.888
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v4.2.3'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Er Er1 0.73058(2) 0.70545(2) 0.49836(2) 0.02452(6) Uani d . . . 1 . .
S S3 0.60044(13) 0.97623(10) 0.14246(7) 0.0334(2) Uani d . . . 1 . .
S S1 0.98508(12) 0.34824(10) 0.85430(6) 0.03257(19) Uani d . . . 1 . .
S S2 0.69734(13) 0.36253(11) 1.18421(7) 0.0373(2) Uani d . . . 1 . .
O O3 0.6693(4) 0.8692(3) 0.35231(19) 0.0331(5) Uani d . . . 1 . .
O O4 0.5675(4) 0.6730(3) 0.37019(19) 0.0350(6) Uani d . . . 1 . .
O O9 0.6979(4) 0.4698(3) 0.5508(2) 0.0440(7) Uani d . . . 1 . .
H H9A 0.7492 0.418 0.6048 0.053 Uiso calc U . R 1 . .
H H9B 0.6336 0.4281 0.5175 0.053 Uiso calc U . R 1 . .
O O2 1.0563(4) 0.4224(3) 0.6253(2) 0.0394(6) Uani d . . . 1 . .
O O5 0.5599(4) 0.2679(3) 1.4040(2) 0.0423(6) Uani d . . . 1 . .
O O1 0.8803(4) 0.6404(3) 0.6282(2) 0.0400(6) Uani d . . . 1 . .
O O8 0.9935(4) 0.8170(3) 0.4446(2) 0.0422(6) Uani d . . . 1 . .
H H8A 1.0753 0.8038 0.4876 0.051 Uiso calc U . R 1 . .
H H8B 1.012 0.8727 0.381 0.051 Uiso calc U . R 1 . .
O O7 0.6543(4) 0.9281(3) 0.5704(2) 0.0400(6) Uani d . . . 1 . .
H H7A 0.6973 0.9374 0.6281 0.048 Uiso calc U . R 1 . .
H H7B 0.5812 1.0067 0.5411 0.048 Uiso calc U . R 1 . .
O O6 0.8168(4) 0.1138(3) 1.4259(2) 0.0387(6) Uani d . . . 1 . .
C C11 0.5915(4) 0.7891(4) 0.3198(2) 0.0265(7) Uani d . . . 1 . .
C C1 0.9481(5) 0.5230(4) 0.6724(2) 0.0269(7) Uani d . . . 1 . .
C C10 0.7232(5) 0.2001(4) 1.3712(3) 0.0295(7) Uani d . . . 1 . .
C C12 0.5321(5) 0.8333(4) 0.2207(3) 0.0277(7) Uani d . . . 1 . .
C C15 0.4935(5) 0.9540(4) 0.0485(2) 0.0267(7) Uani d . . . 1 . .
C C2 0.8913(5) 0.5026(4) 0.7877(3) 0.0274(7) Uani d . . . 1 . .
C C13 0.4299(6) 0.7740(4) 0.1772(3) 0.0368(8) Uani d . . . 1 . .
H H13 0.3805 0.6959 0.2087 0.044 Uiso calc U . R 1 . .
C C9 0.8055(5) 0.2241(4) 1.2572(3) 0.0311(7) Uani d . . . 1 . .
C C14 0.4070(6) 0.8439(4) 0.0791(3) 0.0383(9) Uani d . . . 1 . .
H H14 0.3394 0.8174 0.0392 0.046 Uiso calc U . R 1 . .
C C6 0.8603(5) 0.3170(4) 1.0710(3) 0.0333(8) Uani d . . . 1 . .
C C5 0.8493(5) 0.4042(4) 0.9730(3) 0.0309(7) Uani d . . . 1 . .
C C3 0.7626(6) 0.5917(4) 0.8538(3) 0.0391(9) Uani d . . . 1 . .
H H3 0.6979 0.6806 0.832 0.047 Uiso calc U . R 1 . .
C C4 0.7373(6) 0.5348(5) 0.9596(3) 0.0440(10) Uani d . . . 1 . .
H H4 0.6524 0.582 1.0148 0.053 Uiso calc U . R 1 . .
C C8 0.9572(6) 0.1455(5) 1.1972(3) 0.0482(11) Uani d . . . 1 . .
H H8 1.0327 0.0655 1.2235 0.058 Uiso calc U . R 1 . .
C C7 0.9888(6) 0.1979(5) 1.0905(3) 0.0486(11) Uani d . . . 1 . .
H H7 1.0871 0.1557 1.0388 0.058 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Er1 O1 . 2.245(2) ?
Er1 O2 2_766 2.249(3) ?
Er1 O5 2_667 2.255(3) ?
Er1 O9 . 2.346(3) ?
Er1 O7 . 2.353(3) ?
Er1 O3 . 2.387(2) ?
Er1 O8 . 2.439(3) ?
Er1 O4 . 2.450(2) ?
Er1 C11 . 2.778(3) ?
S3 C12 . 1.716(3) ?
S3 C15 . 1.721(3) ?
S1 C5 . 1.718(3) ?
S1 C2 . 1.718(3) ?
S2 C9 . 1.709(4) ?
S2 C6 . 1.717(4) ?
O3 C11 . 1.268(4) ?
O4 C11 . 1.254(4) ?
O9 H9A . 0.93 ?
O9 H9B . 0.93 ?
O2 C1 . 1.236(4) ?
O2 Er1 2_766 2.249(3) ?
O5 C10 . 1.263(4) ?
O5 Er1 2_667 2.255(3) ?
O1 C1 . 1.257(4) ?
O8 H8A . 0.93 ?
O8 H8B . 0.93 ?
O7 H7A . 0.93 ?
O7 H7B . 0.93 ?
O6 C10 . 1.243(4) ?
C11 C12 . 1.471(4) ?
C1 C2 . 1.471(4) ?
C10 C9 . 1.484(5) ?
C12 C13 . 1.355(5) ?
C15 C14 . 1.358(5) ?
C15 C15 2_675 1.450(6) ?
C2 C3 . 1.351(5) ?
C13 C14 . 1.408(5) ?
C13 H13 . 0.93 ?
C9 C8 . 1.351(6) ?
C14 H14 . 0.93 ?
C6 C7 . 1.364(6) ?
C6 C5 . 1.453(5) ?
C5 C4 . 1.360(5) ?
C3 C4 . 1.410(5) ?
C3 H3 . 0.93 ?
C4 H4 . 0.93 ?
C8 C7 . 1.408(5) ?
C8 H8 . 0.93 ?
C7 H7 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Er1 O2 . 2_766 97.22(10) ?
O1 Er1 O5 . 2_667 98.99(10) ?
O2 Er1 O5 2_766 2_667 144.10(11) ?
O1 Er1 O9 . . 76.85(10) ?
O2 Er1 O9 2_766 . 76.70(10) ?
O5 Er1 O9 2_667 . 76.14(10) ?
O1 Er1 O7 . . 81.74(9) ?
O2 Er1 O7 2_766 . 141.03(10) ?
O5 Er1 O7 2_667 . 73.25(10) ?
O9 Er1 O7 . . 139.06(10) ?
O1 Er1 O3 . . 148.28(10) ?
O2 Er1 O3 2_766 . 84.09(9) ?
O5 Er1 O3 2_667 . 98.04(9) ?
O9 Er1 O3 . . 133.45(10) ?
O7 Er1 O3 . . 77.84(9) ?
O1 Er1 O8 . . 74.50(10) ?
O2 Er1 O8 2_766 . 71.85(10) ?
O5 Er1 O8 2_667 . 143.60(10) ?
O9 Er1 O8 . . 133.77(10) ?
O7 Er1 O8 . . 70.38(10) ?
O3 Er1 O8 . . 75.89(9) ?
O1 Er1 O4 . . 156.65(9) ?
O2 Er1 O4 2_766 . 74.19(10) ?
O5 Er1 O4 2_667 . 78.34(9) ?
O9 Er1 O4 . . 80.01(9) ?
O7 Er1 O4 . . 118.75(9) ?
O3 Er1 O4 . . 53.89(8) ?
O8 Er1 O4 . . 121.12(9) ?
O1 Er1 C11 . . 172.15(10) ?
O2 Er1 C11 2_766 . 76.98(10) ?
O5 Er1 C11 2_667 . 88.75(10) ?
O9 Er1 C11 . . 106.53(10) ?
O7 Er1 C11 . . 99.38(10) ?
O3 Er1 C11 . . 27.10(9) ?
O8 Er1 C11 . . 98.47(10) ?
O4 Er1 C11 . . 26.82(9) ?
C12 S3 C15 . . 91.42(16) ?
C5 S1 C2 . . 91.76(17) ?
C9 S2 C6 . . 91.94(18) ?
C11 O3 Er1 . . 93.87(19) ?
C11 O4 Er1 . . 91.3(2) ?
Er1 O9 H9A . . 120.0 ?
Er1 O9 H9B . . 120.0 ?
H9A O9 H9B . . 120.0 ?
C1 O2 Er1 . 2_766 162.3(2) ?
C10 O5 Er1 . 2_667 154.8(2) ?
C1 O1 Er1 . . 135.0(2) ?
Er1 O8 H8A . . 120.0 ?
Er1 O8 H8B . . 120.0 ?
H8A O8 H8B . . 120.0 ?
Er1 O7 H7A . . 120.0 ?
Er1 O7 H7B . . 120.0 ?
H7A O7 H7B . . 120.0 ?
O4 C11 O3 . . 120.8(3) ?
O4 C11 C12 . . 120.2(3) ?
O3 C11 C12 . . 118.9(3) ?
O4 C11 Er1 . . 61.88(17) ?
O3 C11 Er1 . . 59.04(16) ?
C12 C11 Er1 . . 175.7(2) ?
O2 C1 O1 . . 124.5(3) ?
O2 C1 C2 . . 117.7(3) ?
O1 C1 C2 . . 117.9(3) ?
O6 C10 O5 . . 125.3(3) ?
O6 C10 C9 . . 118.3(3) ?
O5 C10 C9 . . 116.3(3) ?
C13 C12 C11 . . 129.0(3) ?
C13 C12 S3 . . 111.9(2) ?
C11 C12 S3 . . 119.1(3) ?
C14 C15 C15 . 2_675 128.9(4) ?
C14 C15 S3 . . 111.1(2) ?
C15 C15 S3 2_675 . 120.1(3) ?
C3 C2 C1 . . 127.7(3) ?
C3 C2 S1 . . 111.6(3) ?
C1 C2 S1 . . 120.6(3) ?
C12 C13 C14 . . 112.4(3) ?
C12 C13 H13 . . 123.8 ?
C14 C13 H13 . . 123.8 ?
C8 C9 C10 . . 128.8(3) ?
C8 C9 S2 . . 111.7(3) ?
C10 C9 S2 . . 119.5(3) ?
C15 C14 C13 . . 113.3(3) ?
C15 C14 H14 . . 123.4 ?
C13 C14 H14 . . 123.4 ?
C7 C6 C5 . . 129.4(3) ?
C7 C6 S2 . . 110.7(3) ?
C5 C6 S2 . . 119.9(3) ?
C4 C5 C6 . . 127.6(3) ?
C4 C5 S1 . . 110.8(3) ?
C6 C5 S1 . . 121.6(3) ?
C2 C3 C4 . . 112.5(3) ?
C2 C3 H3 . . 123.7 ?
C4 C3 H3 . . 123.7 ?
C5 C4 C3 . . 113.3(3) ?
C5 C4 H4 . . 123.3 ?
C3 C4 H4 . . 123.3 ?
C9 C8 C7 . . 112.7(4) ?
C9 C8 H8 . . 123.6 ?
C7 C8 H8 . . 123.6 ?
C6 C7 C8 . . 113.0(4) ?
C6 C7 H7 . . 123.5 ?
C8 C7 H7 . . 123.5 ?

