# Electronic Supplementary Material (ESI) for ChemComm.
# 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_abs
_database_code_depnum_ccdc_archive 'CCDC 2004590'
loop_
_audit_author_name
_audit_author_address
'Steven Kelley'
;University of Missouri
United States of America
;
_audit_update_record             
;
2020-05-18 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT375_abs                 
;
PROBLEM: Strange C-O-H Geometry (C-O  >   1.45 Ang) .....        O6S Check
RESPONSE: This group is somewhat ambiguous and has been refined unrestrained as a partial occupancy methanol molecule overlapping with a disordered water molecule. The identity of this group is not important in the interpretation of the structure.
;
_vrf_PLAT230_abs                 
;
PROBLEM: Hirshfeld Test Diff for    O3       --C6       .       17.6 s.u.
RESPONSE: This O atom is likely dynamically disordered over a range of positions corresponding to the phenol and quinone tautomers.
;
_vrf_PLAT417_abs                 
;
PROBLEM: Short Inter D-H..H-D       H3       ..H2WA     .       1.95 Ang.
RESPONSE: H atom positions may not be accurate due to the disorder in the structure.
;
# Added during the CSD deposition process: Monday 18 May 2020 09:05 PM
# end Validation Reply Form

_audit_creation_date             2020-05-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C9.25 H19.5 Eu O17 S3, 0.35(C1 H4 O1), 0.65(O)'
_chemical_formula_sum            'C9.60 H21.12 Eu O18 S3'
_chemical_formula_weight         672.72
_chemical_melting_point          ?
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'
Eu Eu -0.1578 3.6682 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.9194(17)
_cell_length_b                   8.8509(17)
_cell_length_c                   25.242(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.154(2)
_cell_angle_gamma                90
_cell_volume                     1992.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9814
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.675
_shelx_estimated_absorpt_T_min   0.415
_exptl_absorpt_coefficient_mu    3.554
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1051 before and 0.0477 after correction.
The Ratio of minimum to maximum transmission is 0.7606.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.242
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1335
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            22691
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.593
_diffrn_reflns_theta_min         1.613
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Source Mo with TRIUMPH optics'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4290
_reflns_number_total             4612
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.915
_refine_diff_density_min         -1.620
_refine_diff_density_rms         0.140
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4612
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0301P)²+7.6453P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0750
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H6S of O6S, H2 of O2, H1 of O1
 At 1.5 times of:
  All C(H,H,H) groups, H3 of O3, All O(H,H,H,H,H,H,H,H,H,H) groups
2. Restrained distances
 O6S-C2S
 1.44 with sigma of 0.02
 O2W-H2WA = O2W-H2WB = O1W-H1WA = O1W-H1WB = O4W-H4WB = O4W-H4WA = O3W-H3WA =
 O3W-H3WB
 0.9 with sigma of 0.02
 O5S-H5W
 0.9 with sigma of 0.02
 O5W-H5WA
 0.9 with sigma of 0.02
3. Others
 Fixed Sof: O5W(0.75) C1S(0.25) H1SA(0.25) H1SB(0.25) H1SC(0.25) O5S(0.25)
 O6S(0.35) H6S(0.35) C2S(0.35) H2SA(0.35) H2SB(0.35) H2SC(0.35) O6WC(0.25)
 O6WB(0.25) O6WA(0.15) H5WA(0.75)
4.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
4.b Tetrahedral OH refined with riding coordinates:
 O1(H1), O2(H2)
4.c Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,H2SC)
4.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6S(H6S)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Eu1 Eu 0.53145(2) 0.46370(2) 0.65931(2) 0.01280(7) Uani 1 1 d . . . . .
S1 S 0.63336(11) 0.87237(11) 0.64747(4) 0.01656(19) Uani 1 1 d . . . . .
O1 O 0.6615(4) 0.9664(4) 0.49595(15) 0.0410(9) Uani 1 1 d . . . . .
H1 H 0.628496 0.894682 0.512849 0.049 Uiso 1 1 calc R U . . .
C1 C 0.8273(4) 0.9736(4) 0.57115(15) 0.0164(8) Uani 1 1 d . . . . .
S2 S 0.64161(10) 1.35823(11) 0.46249(4) 0.01449(18) Uani 1 1 d . . . . .
O2 O 1.0324(4) 1.3372(4) 0.49705(14) 0.0365(8) Uani 1 1 d . . . . .
H2 H 1.103516 1.369671 0.514298 0.044 Uiso 1 1 calc R U . . .
C2 C 0.7741(4) 1.0315(4) 0.52325(15) 0.0156(7) Uani 1 1 d . . . . .
S3 S 1.12260(10) 1.36946(11) 0.64732(4) 0.01683(19) Uani 1 1 d . . . . .
O3 O 1.0111(9) 0.9852(8) 0.6391(3) 0.099(2) Uani 1 1 d . . . . .
H3 H 1.034271 1.053668 0.659474 0.148 Uiso 1 1 calc R U . . .
C3 C 0.8419(4) 1.1568(4) 0.49926(15) 0.0143(7) Uani 1 1 d . . . . .
O4 O 0.7106(4) 0.9705(4) 0.68529(12) 0.0267(7) Uani 1 1 d . . . . .
C4 C 0.9660(4) 1.2234(4) 0.52396(15) 0.0156(7) Uani 1 1 d . . . . .
O5 O 0.5954(3) 0.7270(3) 0.67186(11) 0.0205(6) Uani 1 1 d . . . . .
C5 C 1.0216(4) 1.1683(5) 0.57187(15) 0.0164(7) Uani 1 1 d . . . . .
O6 O 0.5036(3) 0.9461(3) 0.62411(13) 0.0253(7) Uani 1 1 d . . . . .
C6 C 0.9503(4) 1.0446(5) 0.59454(15) 0.0172(8) Uani 1 1 d . . . . .
O7 O 0.5247(3) 1.2828(3) 0.49271(11) 0.0206(6) Uani 1 1 d . . . . .
C7 C 0.7629(5) 0.8336(4) 0.59562(16) 0.0192(8) Uani 1 1 d . . . . .
H7A H 0.844034 0.772437 0.609618 0.023 Uiso 1 1 calc R U . . .
H7B H 0.712549 0.775278 0.568329 0.023 Uiso 1 1 calc R U . . .
O8 O 0.5843(3) 1.4123(3) 0.41137(12) 0.0229(6) Uani 1 1 d . . . . .
C8 C 0.7805(4) 1.2199(4) 0.44827(15) 0.0158(7) Uani 1 1 d . . . . .
H8A H 0.736778 1.139130 0.427324 0.019 Uiso 1 1 calc R U . . .
H8B H 0.860887 1.265186 0.427938 0.019 Uiso 1 1 calc R U . . .
O9 O 0.7157(3) 1.4785(3) 0.49185(12) 0.0203(6) Uani 1 1 d . . . . .
C9 C 1.1605(4) 1.2316(5) 0.59761(15) 0.0185(8) Uani 1 1 d . . . . .
H9A H 1.222883 1.277071 0.570515 0.022 Uiso 1 1 calc R U . . .
H9B H 1.216849 1.149386 0.613429 0.022 Uiso 1 1 calc R U . . .
O10 O 1.0458(3) 1.4949(3) 0.62156(12) 0.0242(6) Uani 1 1 d . . . . .
O11 O 1.2686(3) 1.4121(4) 0.66928(12) 0.0238(6) Uani 1 1 d . . . . .
O12 O 1.0293(3) 1.2993(4) 0.68829(11) 0.0241(6) Uani 1 1 d . . . . .
O4W O 0.7401(3) 0.4813(3) 0.59957(11) 0.0192(6) Uani 1 1 d D . . . .
O3W O 0.5136(3) 0.2545(3) 0.59931(11) 0.0206(6) Uani 1 1 d D . . . .
O5W O 0.5234(15) 0.2292(14) 0.7111(5) 0.033(2) Uani 0.75 1 d D . P A 2
O2W O 0.4588(4) 0.5389(4) 0.74720(13) 0.0315(8) Uani 1 1 d D . . . .
O1W O 0.7602(4) 0.4378(5) 0.70805(13) 0.0386(9) Uani 1 1 d D . . . .
C1S C 0.451(2) 0.183(3) 0.7578(8) 0.036(5) Uiso 0.25 1 d . . P A 1
H1SA H 0.528895 0.200749 0.783473 0.053 Uiso 0.25 1 calc R U P A 1
H1SB H 0.419750 0.079640 0.759570 0.053 Uiso 0.25 1 calc R U P A 1
H1SC H 0.367438 0.247956 0.765201 0.053 Uiso 0.25 1 calc R U P A 1
O5S O 0.510(4) 0.217(5) 0.7028(14) 0.022(7) Uiso 0.25 1 d D . P A 1
O6S O 0.3165(12) -0.0377(13) 0.7150(4) 0.036(2) Uiso 0.35 1 d D . P B 3
H6S H 0.295335 0.038879 0.698271 0.043 Uiso 0.35 1 calc R U P B 3
C2S C 0.221(2) -0.176(2) 0.6927(8) 0.056(5) Uiso 0.35 1 d D . P B 3
H2SA H 0.266307 -0.212884 0.660636 0.084 Uiso 0.35 1 calc R U P B 3
H2SB H 0.120652 -0.143638 0.685371 0.084 Uiso 0.35 1 calc R U P B 3
H2SC H 0.219452 -0.255726 0.718535 0.084 Uiso 0.35 1 calc R U P B 3
O6WC O 0.4539(17) 0.2357(17) 0.8092(6) 0.038(3) Uiso 0.25 1 d . . P C 2
O6WB O 0.2878(19) -0.115(2) 0.7105(7) 0.043(4) Uiso 0.25 1 d . . P D 1
O6WA O 0.240(3) -0.065(3) 0.6855(12) 0.049(7) Uiso 0.15 1 d . . P E 2
H4WA H 0.735(9) 0.470(8) 0.5643(9) 0.074 Uiso 1 1 d D U . . .
H4WB H 0.840(3) 0.486(9) 0.604(3) 0.074 Uiso 1 1 d D U . . .
H3WA H 0.517(8) 0.270(9) 0.5646(9) 0.074 Uiso 1 1 d D U . . .
H3WB H 0.505(8) 0.155(3) 0.604(3) 0.074 Uiso 1 1 d D U . . .
H5W H 0.595(7) 0.163(8) 0.700(3) 0.074 Uiso 1 1 d D U . . .
H2WA H 0.481(8) 0.620(5) 0.767(3) 0.074 Uiso 1 1 d D U . . .
H2WB H 0.385(6) 0.498(8) 0.767(3) 0.074 Uiso 1 1 d D U . . .
H1WA H 0.758(9) 0.447(9) 0.7429(9) 0.074 Uiso 1 1 d D U . . .
H1WB H 0.838(6) 0.386(8) 0.695(3) 0.074 Uiso 1 1 d D U . . .
H5WA H 0.450(9) 0.177(11) 0.729(4) 0.074 Uiso 0.75 1 d D U P F 2


_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
Eu1 O5 2.420(3) . ?
Eu1 O8 2.333(3) 3_676 ?
Eu1 O11 2.402(3) 1_445 ?
Eu1 O4W 2.404(3) . ?
Eu1 O3W 2.397(3) . ?
Eu1 O5W 2.454(13) . ?
Eu1 O2W 2.407(3) . ?
Eu1 O1W 2.391(3) . ?
Eu1 O5S 2.45(4) . ?
S1 O4 1.462(3) . ?
S1 O5 1.466(3) . ?
S1 O6 1.452(3) . ?
S1 C7 1.781(4) . ?
O1 H1 0.8200 . ?
O1 C2 1.346(5) . ?
C1 C2 1.395(5) . ?
C1 C6 1.394(6) . ?
C1 C7 1.500(5) . ?
S2 O7 1.456(3) . ?
S2 O8 1.467(3) . ?
S2 C8 1.779(4) . ?
S2 O9 1.455(3) . ?
O2 H2 0.8200 . ?
O2 C4 1.353(5) . ?
C2 C3 1.402(5) . ?
S3 C9 1.783(4) . ?
S3 O10 1.457(3) . ?
S3 O11 1.464(3) . ?
S3 O12 1.467(3) . ?
O3 H3 0.8200 . ?
O3 C6 1.354(8) . ?
C3 C4 1.399(5) . ?
C3 C8 1.504(5) . ?
C4 C5 1.394(5) . ?
C5 C6 1.390(6) . ?
C5 C9 1.506(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O4W H4WA 0.90(2) . ?
O4W H4WB 0.90(2) . ?
O3W H3WA 0.89(2) . ?
O3W H3WB 0.89(2) . ?
O5W H5W 0.91(5) . ?
O5W H5WA 0.91(2) . ?
O2W H2WA 0.90(2) . ?
O2W H2WB 0.91(2) . ?
O1W H1WA 0.88(2) . ?
O1W H1WB 0.89(2) . ?
C1S H1SA 0.9600 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?
C1S O5S 1.52(4) . ?
O5S H5W 0.89(2) . ?
O6S H6S 0.8200 . ?
O6S C2S 1.593(15) . ?
C2S H2SA 0.9600 . ?
C2S H2SB 0.9600 . ?
C2S H2SC 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
O5 Eu1 O5W 138.8(3) . . ?
O5 Eu1 O5S 144.8(8) . . ?
O8 Eu1 O5 75.56(10) 3_676 . ?
O8 Eu1 O11 74.91(11) 3_676 1_445 ?
O8 Eu1 O4W 80.30(10) 3_676 . ?
O8 Eu1 O3W 81.48(11) 3_676 . ?
O8 Eu1 O5W 142.3(3) 3_676 . ?
O8 Eu1 O2W 117.06(12) 3_676 . ?
O8 Eu1 O1W 144.48(13) 3_676 . ?
O8 Eu1 O5S 136.7(8) 3_676 . ?
O11 Eu1 O5 113.51(11) 1_445 . ?
O11 Eu1 O4W 146.68(10) 1_445 . ?
O11 Eu1 O5W 75.7(3) 1_445 . ?
O11 Eu1 O2W 71.98(11) 1_445 . ?
O11 Eu1 O5S 73.0(8) 1_445 . ?
O4W Eu1 O5 80.62(10) . . ?
O4W Eu1 O5W 114.4(3) . . ?
O4W Eu1 O2W 140.46(11) . . ?
O4W Eu1 O5S 113.5(8) . . ?
O3W Eu1 O5 147.34(10) . . ?
O3W Eu1 O11 81.74(10) . 1_445 ?
O3W Eu1 O4W 72.79(10) . . ?
O3W Eu1 O5W 71.4(3) . . ?
O3W Eu1 O2W 141.12(11) . . ?
O3W Eu1 O5S 65.8(8) . . ?
O2W Eu1 O5 71.15(10) . . ?
O2W Eu1 O5W 74.6(3) . . ?
O2W Eu1 O5S 79.2(8) . . ?
O1W Eu1 O5 79.89(13) . . ?
O1W Eu1 O11 139.42(12) . 1_445 ?
O1W Eu1 O4W 70.61(11) . . ?
O1W Eu1 O3W 107.83(12) . . ?
O1W Eu1 O5W 70.8(3) . . ?
O1W Eu1 O2W 77.50(12) . . ?
O1W Eu1 O5S 75.5(8) . . ?
O4 S1 O5 110.86(17) . . ?
O4 S1 C7 106.8(2) . . ?
O5 S1 C7 106.89(18) . . ?
O6 S1 O4 111.83(19) . . ?
O6 S1 O5 112.34(18) . . ?
O6 S1 C7 107.80(19) . . ?
C2 O1 H1 109.5 . . ?
C2 C1 C7 122.0(4) . . ?
C6 C1 C2 117.8(4) . . ?
C6 C1 C7 120.0(4) . . ?
O7 S2 O8 111.23(18) . . ?
O7 S2 C8 106.84(18) . . ?
O8 S2 C8 106.75(18) . . ?
O9 S2 O7 113.19(18) . . ?
O9 S2 O8 111.49(18) . . ?
O9 S2 C8 106.91(18) . . ?
C4 O2 H2 109.5 . . ?
O1 C2 C1 122.6(4) . . ?
O1 C2 C3 116.1(4) . . ?
C1 C2 C3 121.3(4) . . ?
O10 S3 C9 107.29(19) . . ?
O10 S3 O11 112.89(19) . . ?
O10 S3 O12 111.74(18) . . ?
O11 S3 C9 105.83(18) . . ?
O11 S3 O12 110.37(18) . . ?
O12 S3 C9 108.40(19) . . ?
C6 O3 H3 109.5 . . ?
C2 C3 C8 120.4(3) . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 C8 120.7(3) . . ?
O2 C4 C3 115.9(3) . . ?
O2 C4 C5 122.8(4) . . ?
C5 C4 C3 121.2(3) . . ?
S1 O5 Eu1 147.63(17) . . ?
C4 C5 C9 122.3(4) . . ?
C6 C5 C4 118.1(4) . . ?
C6 C5 C9 119.5(4) . . ?
O3 C6 C1 119.3(5) . . ?
O3 C6 C5 117.7(5) . . ?
C5 C6 C1 122.8(4) . . ?
S1 C7 H7A 108.9 . . ?
S1 C7 H7B 108.9 . . ?
C1 C7 S1 113.2(3) . . ?
C1 C7 H7A 108.9 . . ?
C1 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
S2 O8 Eu1 168.1(2) . 3_676 ?
S2 C8 H8A 109.8 . . ?
S2 C8 H8B 109.8 . . ?
C3 C8 S2 109.5(3) . . ?
C3 C8 H8A 109.8 . . ?
C3 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
S3 C9 H9A 108.8 . . ?
S3 C9 H9B 108.8 . . ?
C5 C9 S3 113.6(3) . . ?
C5 C9 H9A 108.8 . . ?
C5 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
S3 O11 Eu1 151.28(18) . 1_665 ?
Eu1 O4W H4WA 125(5) . . ?
Eu1 O4W H4WB 134(5) . . ?
H4WA O4W H4WB 100(7) . . ?
Eu1 O3W H3WA 120(5) . . ?
Eu1 O3W H3WB 133(5) . . ?
H3WA O3W H3WB 107(7) . . ?
Eu1 O5W H5W 111(5) . . ?
Eu1 O5W H5WA 135(7) . . ?
H5W O5W H5WA 109(8) . . ?
Eu1 O2W H2WA 133(5) . . ?
Eu1 O2W H2WB 127(5) . . ?
H2WA O2W H2WB 99(6) . . ?
Eu1 O1W H1WA 119(5) . . ?
Eu1 O1W H1WB 122(5) . . ?
H1WA O1W H1WB 115(7) . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
O5S C1S H1SA 109.5 . . ?
O5S C1S H1SB 109.5 . . ?
O5S C1S H1SC 109.5 . . ?
Eu1 O5S H5W 112(6) . . ?
C1S O5S Eu1 128(2) . . ?
C1S O5S H5W 105(6) . . ?
C2S O6S H6S 109.5 . . ?
O6S C2S H2SA 109.5 . . ?
O6S C2S H2SB 109.5 . . ?
O6S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 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
O1 C2 C3 C4 -175.8(4) . . . . ?
O1 C2 C3 C8 5.1(5) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C1 C2 C3 C8 -178.5(4) . . . . ?
O2 C4 C5 C6 -175.9(4) . . . . ?
O2 C4 C5 C9 0.1(6) . . . . ?
C2 C1 C6 O3 -175.6(5) . . . . ?
C2 C1 C6 C5 -0.6(6) . . . . ?
C2 C1 C7 S1 -100.2(4) . . . . ?
C2 C3 C4 O2 175.6(4) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C2 C3 C8 S2 89.1(4) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C3 C4 C5 C9 176.2(4) . . . . ?
O4 S1 O5 Eu1 -159.1(3) . . . . ?
O4 S1 C7 C1 -54.1(3) . . . . ?
C4 C3 C8 S2 -90.0(4) . . . . ?
C4 C5 C6 C1 0.6(6) . . . . ?
C4 C5 C6 O3 175.5(5) . . . . ?
C4 C5 C9 S3 96.6(4) . . . . ?
O5 S1 C7 C1 -172.8(3) . . . . ?
O6 S1 O5 Eu1 74.9(4) . . . . ?
O6 S1 C7 C1 66.2(3) . . . . ?
C6 C1 C2 O1 176.3(4) . . . . ?
C6 C1 C2 C3 0.0(6) . . . . ?
C6 C1 C7 S1 84.0(4) . . . . ?
C6 C5 C9 S3 -87.4(4) . . . . ?
O7 S2 O8 Eu1 73.8(10) . . . 3_676 ?
O7 S2 C8 C3 -59.6(3) . . . . ?
C7 S1 O5 Eu1 -43.1(4) . . . . ?
C7 C1 C2 O1 0.3(6) . . . . ?
C7 C1 C2 C3 -175.9(4) . . . . ?
C7 C1 C6 O3 0.5(7) . . . . ?
C7 C1 C6 C5 175.4(4) . . . . ?
O8 S2 C8 C3 -178.7(3) . . . . ?
C8 S2 O8 Eu1 -170.0(9) . . . 3_676 ?
C8 C3 C4 O2 -5.3(5) . . . . ?
C8 C3 C4 C5 178.4(4) . . . . ?
O9 S2 O8 Eu1 -53.6(10) . . . 3_676 ?
O9 S2 C8 C3 61.8(3) . . . . ?
C9 S3 O11 Eu1 36.8(5) . . . 1_665 ?
C9 C5 C6 C1 -175.6(4) . . . . ?
C9 C5 C6 O3 -0.6(7) . . . . ?
O10 S3 C9 C5 -61.8(3) . . . . ?
O10 S3 O11 Eu1 -80.2(4) . . . 1_665 ?
O11 S3 C9 C5 177.4(3) . . . . ?
O12 S3 C9 C5 59.0(3) . . . . ?
O12 S3 O11 Eu1 153.9(4) . . . 1_665 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_abs_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2004591'
loop_
_audit_author_name
_audit_author_address
'Steven Kelley'
;University of Missouri
United States of America
;
_audit_update_record             
;
2020-05-18 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_abs                 
;
PROBLEM: Hirshfeld Test Diff for    O3       --C6       .       12.9 s.u.
RESPONSE: This O atom is likely dynamically disordered across a range of positions corresponding to the phenol and quinone tautomers for this molecule.
;
_vrf_PLAT414_abs                 
;
PROBLEM: Short Intra D-H..H-X       H1       ..H7B              1.89 Ang.
RESPONSE: H atom positions may not be accurate due to the disorder in the structure.
;
_vrf_PLAT976_abs                 
;
PROBLEM: Check Calcd Resid. Dens.  0.60A   From O3             -1.57 eA-3
RESPONSE: H atom positions may not be accurate due to the disorder in the structure.
;
# Added during the CSD deposition process: Monday 18 May 2020 09:07 PM
# end Validation Reply Form

_audit_creation_date             2020-05-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C9.25 H18.75 O17 S3 Sm, 0.35(C1 H4 O1), 0.65(O)'
_chemical_formula_sum            'C9.60 H19.50 O18 S3 Sm'
_chemical_formula_weight         669.48
_chemical_melting_point          ?
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'
Sm Sm -0.1638 3.4418 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.9342(15)
_cell_length_b                   8.8762(15)
_cell_length_c                   25.291(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.340(2)
_cell_angle_gamma                90
_cell_volume                     2005.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      28.48
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.618
_shelx_estimated_absorpt_T_min   0.435
_exptl_absorpt_coefficient_mu    3.331
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1135 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.7522.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.217
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1324
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23152
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.705
_diffrn_reflns_theta_min         1.610
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Source Mo with TRIUMPH optics'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4729
_reflns_number_total             4866
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.081
_refine_diff_density_min         -1.627
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.254
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4866
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.253
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0225P)²+12.4473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0879
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H6S of O6S, H2 of O2, H1 of O1
 At 1.5 times of:
  All C(H,H,H) groups, H3 of O3, All O(H,H,H,H,H,H,H,H,H) groups
2. Restrained distances
 O2W-H2WB = O2W-H2WA = O1W-H1WA = O1W-H1WB = O4W-H4WB = O4W-H4WA = O3W-H3WA =
 O3W-H3WB = O5S-H5W = O5W-H5W
 0.9 with sigma of 0.02
3. Others
 Fixed Sof: O5W(0.75) C1S(0.25) H1SA(0.25) H1SB(0.25) H1SC(0.25) O5S(0.25)
 O6S(0.35) H6S(0.35) C2S(0.35) H2SA(0.35) H2SB(0.35) H2SC(0.35) O6WC(0.25)
 O6WB(0.25) O6WA(0.15)
4.a Riding coordinates:
 C2S(H2SA,H2SB,H2SC)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
4.c Tetrahedral OH refined with riding coordinates:
 O1(H1), O2(H2)
4.d Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC)
4.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6S(H6S)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   difmap
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
Sm1 Sm 0.53270(2) 0.46389(2) 0.65925(2) 0.01326(7) Uani 1 1 d . . . . .
S1 S 0.63446(13) 0.87304(12) 0.64724(4) 0.0169(2) Uani 1 1 d . . . . .
O1 O 0.6615(5) 0.9667(5) 0.49606(18) 0.0402(10) Uani 1 1 d . . . . .
H1 H 0.627995 0.893524 0.513393 0.048 Uiso 1 1 calc R U . . .
C1 C 0.8281(5) 0.9742(5) 0.57112(17) 0.0162(8) Uani 1 1 d . . . . .
S2 S 0.64172(12) 1.35805(12) 0.46264(4) 0.0145(2) Uani 1 1 d . . . . .
O2 O 1.0318(5) 1.3370(5) 0.49696(16) 0.0353(9) Uani 1 1 d . . . . .
H2 H 1.104679 1.370506 0.514500 0.042 Uiso 1 1 calc R U . . .
C2 C 0.7741(5) 1.0320(5) 0.52328(17) 0.0162(8) Uani 1 1 d . . . . .
S3 S 1.12337(12) 1.36856(13) 0.64720(4) 0.0172(2) Uani 1 1 d . . . . .
O3 O 1.0126(10) 0.9870(11) 0.6386(4) 0.103(3) Uani 1 1 d . . . . .
H3 H 0.944602 0.956164 0.658683 0.155 Uiso 1 1 calc R U . . .
C3 C 0.8413(5) 1.1572(5) 0.49943(17) 0.0142(8) Uani 1 1 d . . . . .
O4 O 0.7113(4) 0.9712(4) 0.68514(14) 0.0267(8) Uani 1 1 d . . . . .
C4 C 0.9662(5) 1.2234(5) 0.52401(17) 0.0165(8) Uani 1 1 d . . . . .
O5 O 0.5969(4) 0.7282(4) 0.67152(13) 0.0213(7) Uani 1 1 d . . . . .
C5 C 1.0216(5) 1.1680(5) 0.57180(17) 0.0167(8) Uani 1 1 d . . . . .
O6 O 0.5049(4) 0.9467(4) 0.62381(15) 0.0258(7) Uani 1 1 d . . . . .
C6 C 0.9513(5) 1.0444(5) 0.59451(17) 0.0175(9) Uani 1 1 d . . . . .
O7 O 0.5244(4) 1.2830(4) 0.49267(13) 0.0207(7) Uani 1 1 d . . . . .
C7 C 0.7638(5) 0.8336(5) 0.59559(18) 0.0194(9) Uani 1 1 d . . . . .
H7A H 0.846610 0.771476 0.609975 0.023 Uiso 1 1 calc R U . . .
H7B H 0.712531 0.774033 0.567772 0.023 Uiso 1 1 calc R U . . .
O8 O 0.5848(4) 1.4119(4) 0.41150(13) 0.0230(7) Uani 1 1 d . . . . .
C8 C 0.7800(5) 1.2201(5) 0.44845(17) 0.0153(8) Uani 1 1 d . . . . .
H8A H 0.735337 1.137999 0.427061 0.018 Uiso 1 1 calc R U . . .
H8B H 0.861958 1.266159 0.427816 0.018 Uiso 1 1 calc R U . . .
O9 O 0.7157(4) 1.4783(4) 0.49205(13) 0.0213(7) Uani 1 1 d . . . . .
C9 C 1.1613(5) 1.2312(5) 0.59752(18) 0.0192(9) Uani 1 1 d . . . . .
H9A H 1.224505 1.277505 0.569924 0.023 Uiso 1 1 calc R U . . .
H9B H 1.218812 1.147422 0.613609 0.023 Uiso 1 1 calc R U . . .
O10 O 1.0470(4) 1.4944(4) 0.62148(14) 0.0244(7) Uani 1 1 d . . . . .
O11 O 1.2694(4) 1.4112(4) 0.66924(13) 0.0235(7) Uani 1 1 d . . . . .
O12 O 1.0298(4) 1.2985(4) 0.68789(13) 0.0245(7) Uani 1 1 d . . . . .
O4W O 0.7416(4) 0.4820(4) 0.59914(13) 0.0199(7) Uani 1 1 d D . . . .
O3W O 0.5141(4) 0.2547(4) 0.59899(13) 0.0210(7) Uani 1 1 d D . . . .
O5W O 0.5276(15) 0.2298(14) 0.7107(6) 0.035(3) Uani 0.75 1 d D . P A 2
O2W O 0.4606(5) 0.5390(5) 0.74771(15) 0.0353(10) Uani 1 1 d D . . . .
O1W O 0.7632(4) 0.4390(6) 0.70834(15) 0.0379(10) Uani 1 1 d D . . . .
C1S C 0.448(3) 0.182(3) 0.7552(10) 0.039(5) Uiso 0.25 1 d . . P A 1
H1SA H 0.517350 0.217601 0.782865 0.059 Uiso 0.25 1 calc R U P A 1
H1SB H 0.433183 0.073549 0.758940 0.059 Uiso 0.25 1 calc R U P A 1
H1SC H 0.352280 0.234407 0.758664 0.059 Uiso 0.25 1 calc R U P A 1
O5S O 0.510(3) 0.213(4) 0.7053(18) 0.018(6) Uiso 0.25 1 d D . P A 1
O6S O 0.3181(16) -0.0358(17) 0.7159(6) 0.045(3) Uiso 0.35 1 d . . P B 3
H6S H 0.289370 0.041885 0.699849 0.053 Uiso 0.35 1 calc R U P B 3
C2S C 0.213(2) -0.198(2) 0.6919(8) 0.047(5) Uiso 0.35 1 d . . P B 3
H2SA H 0.212526 -0.198552 0.653161 0.070 Uiso 0.35 1 d R U P B 3
H2SB H 0.260156 -0.291212 0.704871 0.070 Uiso 0.35 1 d R U P B 3
H2SC H 0.110326 -0.192402 0.704871 0.070 Uiso 0.35 1 d R U P B 3
O6WC O 0.4498(17) 0.2394(17) 0.8095(6) 0.029(3) Uiso 0.25 1 d . . P C 2
O6WB O 0.286(2) -0.117(2) 0.7100(8) 0.045(4) Uiso 0.25 1 d . . P D 1
O6WA O 0.240(4) -0.070(4) 0.6853(15) 0.055(9) Uiso 0.15 1 d . . P E 2
H4WA H 0.726(11) 0.478(11) 0.5641(10) 0.083 Uiso 1 1 d D U . . .
H4WB H 0.841(3) 0.487(11) 0.604(4) 0.083 Uiso 1 1 d D U . . .
H3WA H 0.513(11) 0.271(11) 0.5642(10) 0.083 Uiso 1 1 d D U . . .
H3WB H 0.504(11) 0.155(3) 0.602(4) 0.083 Uiso 1 1 d D U . . .
H5W H 0.594(8) 0.159(9) 0.702(4) 0.083 Uiso 1 1 d D U . . .
H2WA H 0.500(10) 0.617(7) 0.766(3) 0.083 Uiso 1 1 d D U . . .
H2WB H 0.388(8) 0.498(10) 0.768(3) 0.083 Uiso 1 1 d D U . . .
H1WA H 0.763(11) 0.452(11) 0.7433(10) 0.083 Uiso 1 1 d D U . . .
H1WB H 0.846(7) 0.391(10) 0.697(4) 0.083 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
Sm1 O5 2.435(3) . ?
Sm1 O8 2.344(3) 3_676 ?
Sm1 O11 2.413(3) 1_445 ?
Sm1 O4W 2.419(3) . ?
Sm1 O3W 2.407(3) . ?
Sm1 O5W 2.451(15) . ?
Sm1 O2W 2.425(4) . ?
Sm1 O1W 2.408(4) . ?
Sm1 O5S 2.52(5) . ?
S1 O4 1.463(4) . ?
S1 O5 1.465(3) . ?
S1 O6 1.452(4) . ?
S1 C7 1.784(5) . ?
O1 H1 0.8400 . ?
O1 C2 1.347(6) . ?
C1 C2 1.397(6) . ?
C1 C6 1.393(6) . ?
C1 C7 1.509(6) . ?
S2 O7 1.459(3) . ?
S2 O8 1.467(3) . ?
S2 C8 1.778(5) . ?
S2 O9 1.457(3) . ?
O2 H2 0.8400 . ?
O2 C4 1.354(6) . ?
C2 C3 1.401(6) . ?
S3 C9 1.785(5) . ?
S3 O10 1.460(4) . ?
S3 O11 1.465(3) . ?
S3 O12 1.468(3) . ?
O3 H3 0.8400 . ?
O3 C6 1.340(10) . ?
C3 C4 1.403(6) . ?
C3 C8 1.505(6) . ?
C4 C5 1.393(6) . ?
C5 C6 1.390(6) . ?
C5 C9 1.511(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
O4W H4WA 0.90(2) . ?
O4W H4WB 0.90(2) . ?
O3W H3WA 0.89(2) . ?
O3W H3WB 0.89(2) . ?
O5W H5W 0.89(2) . ?
O2W H2WA 0.90(2) . ?
O2W H2WB 0.91(2) . ?
O1W H1WA 0.89(2) . ?
O1W H1WB 0.90(2) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C1S O5S 1.41(5) . ?
O5S H5W 0.90(2) . ?
O6S H6S 0.8400 . ?
O6S C2S 1.82(3) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 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
O5 Sm1 O5W 139.0(3) . . ?
O5 Sm1 O5S 144.3(9) . . ?
O8 Sm1 O5 75.41(12) 3_676 . ?
O8 Sm1 O11 74.86(12) 3_676 1_445 ?
O8 Sm1 O4W 80.38(12) 3_676 . ?
O8 Sm1 O3W 81.41(12) 3_676 . ?
O8 Sm1 O5W 142.5(4) 3_676 . ?
O8 Sm1 O2W 117.03(15) 3_676 . ?
O8 Sm1 O1W 144.50(15) 3_676 . ?
O8 Sm1 O5S 136.9(9) 3_676 . ?
O11 Sm1 O5 113.74(12) 1_445 . ?
O11 Sm1 O4W 146.59(11) 1_445 . ?
O11 Sm1 O5W 76.1(3) 1_445 . ?
O11 Sm1 O2W 72.08(13) 1_445 . ?
O11 Sm1 O5S 72.4(7) 1_445 . ?
O4W Sm1 O5 80.45(12) . . ?
O4W Sm1 O5W 114.0(3) . . ?
O4W Sm1 O2W 140.48(13) . . ?
O4W Sm1 O5S 114.5(7) . . ?
O3W Sm1 O5 147.06(11) . . ?
O3W Sm1 O11 81.55(12) . 1_445 ?
O3W Sm1 O4W 72.78(12) . . ?
O3W Sm1 O5W 71.4(3) . . ?
O3W Sm1 O2W 141.12(12) . . ?
O3W Sm1 O1W 108.13(14) . . ?
O3W Sm1 O5S 66.8(9) . . ?
O2W Sm1 O5 71.40(12) . . ?
O2W Sm1 O5W 74.8(3) . . ?
O2W Sm1 O5S 78.1(8) . . ?
O1W Sm1 O5 79.78(15) . . ?
O1W Sm1 O11 139.40(13) . 1_445 ?
O1W Sm1 O4W 70.70(12) . . ?
O1W Sm1 O5W 70.6(4) . . ?
O1W Sm1 O2W 77.33(15) . . ?
O1W Sm1 O5S 75.7(8) . . ?
O4 S1 O5 110.8(2) . . ?
O4 S1 C7 107.1(2) . . ?
O5 S1 C7 106.6(2) . . ?
O6 S1 O4 111.6(2) . . ?
O6 S1 O5 112.5(2) . . ?
O6 S1 C7 107.9(2) . . ?
C2 O1 H1 109.5 . . ?
C2 C1 C7 121.9(4) . . ?
C6 C1 C2 118.1(4) . . ?
C6 C1 C7 119.8(4) . . ?
O7 S2 O8 111.2(2) . . ?
O7 S2 C8 107.0(2) . . ?
O8 S2 C8 106.5(2) . . ?
O9 S2 O7 113.2(2) . . ?
O9 S2 O8 111.4(2) . . ?
O9 S2 C8 107.1(2) . . ?
C4 O2 H2 109.5 . . ?
O1 C2 C1 122.6(4) . . ?
O1 C2 C3 116.2(4) . . ?
C1 C2 C3 121.1(4) . . ?
O10 S3 C9 107.4(2) . . ?
O10 S3 O11 112.6(2) . . ?
O10 S3 O12 111.7(2) . . ?
O11 S3 C9 105.8(2) . . ?
O11 S3 O12 110.6(2) . . ?
O12 S3 C9 108.4(2) . . ?
C6 O3 H3 109.5 . . ?
C2 C3 C4 118.9(4) . . ?
C2 C3 C8 120.6(4) . . ?
C4 C3 C8 120.6(4) . . ?
O2 C4 C3 115.7(4) . . ?
O2 C4 C5 123.3(4) . . ?
C5 C4 C3 120.9(4) . . ?
S1 O5 Sm1 147.9(2) . . ?
C4 C5 C9 122.1(4) . . ?
C6 C5 C4 118.5(4) . . ?
C6 C5 C9 119.3(4) . . ?
O3 C6 C1 120.1(6) . . ?
O3 C6 C5 117.4(6) . . ?
C5 C6 C1 122.4(4) . . ?
S1 C7 H7A 109.0 . . ?
S1 C7 H7B 109.0 . . ?
C1 C7 S1 112.8(3) . . ?
C1 C7 H7A 109.0 . . ?
C1 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
S2 O8 Sm1 167.8(2) . 3_676 ?
S2 C8 H8A 109.8 . . ?
S2 C8 H8B 109.8 . . ?
C3 C8 S2 109.4(3) . . ?
C3 C8 H8A 109.8 . . ?
C3 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
S3 C9 H9A 108.9 . . ?
S3 C9 H9B 108.9 . . ?
C5 C9 S3 113.4(3) . . ?
C5 C9 H9A 108.9 . . ?
C5 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
S3 O11 Sm1 151.2(2) . 1_665 ?
Sm1 O4W H4WA 120(6) . . ?
Sm1 O4W H4WB 133(6) . . ?
H4WA O4W H4WB 106(8) . . ?
Sm1 O3W H3WA 120(6) . . ?
Sm1 O3W H3WB 135(6) . . ?
H3WA O3W H3WB 105(8) . . ?
Sm1 O5W H5W 116(7) . . ?
Sm1 O2W H2WA 125(6) . . ?
Sm1 O2W H2WB 127(6) . . ?
H2WA O2W H2WB 108(8) . . ?
Sm1 O1W H1WA 120(7) . . ?
Sm1 O1W H1WB 126(6) . . ?
H1WA O1W H1WB 112(8) . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
O5S C1S H1SA 109.5 . . ?
O5S C1S H1SB 109.5 . . ?
O5S C1S H1SC 109.5 . . ?
Sm1 O5S H5W 111(7) . . ?
C1S O5S Sm1 128(2) . . ?
C1S O5S H5W 109(7) . . ?
C2S O6S H6S 109.5 . . ?
O6S C2S H2SA 109.6 . . ?
O6S C2S H2SB 109.7 . . ?
O6S C2S H2SC 109.1 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 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
O1 C2 C3 C4 -175.4(4) . . . . ?
O1 C2 C3 C8 4.8(6) . . . . ?
C1 C2 C3 C4 1.0(6) . . . . ?
C1 C2 C3 C8 -178.8(4) . . . . ?
O2 C4 C5 C6 -175.8(4) . . . . ?
O2 C4 C5 C9 -0.1(7) . . . . ?
C2 C1 C6 O3 -175.7(6) . . . . ?
C2 C1 C6 C5 -0.4(7) . . . . ?
C2 C1 C7 S1 -100.0(5) . . . . ?
C2 C3 C4 O2 175.5(4) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C2 C3 C8 S2 89.4(4) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
C3 C4 C5 C9 176.3(4) . . . . ?
O4 S1 O5 Sm1 -159.4(4) . . . . ?
O4 S1 C7 C1 -54.2(4) . . . . ?
C4 C3 C8 S2 -90.4(4) . . . . ?
C4 C5 C6 C1 0.2(7) . . . . ?
C4 C5 C6 O3 175.6(6) . . . . ?
C4 C5 C9 S3 96.7(5) . . . . ?
O5 S1 C7 C1 -172.8(3) . . . . ?
O6 S1 O5 Sm1 74.8(4) . . . . ?
O6 S1 C7 C1 66.1(4) . . . . ?
C6 C1 C2 O1 176.0(4) . . . . ?
C6 C1 C2 C3 -0.2(7) . . . . ?
C6 C1 C7 S1 84.4(5) . . . . ?
C6 C5 C9 S3 -87.6(5) . . . . ?
O7 S2 O8 Sm1 72.1(11) . . . 3_676 ?
O7 S2 C8 C3 -59.8(3) . . . . ?
C7 S1 O5 Sm1 -43.3(5) . . . . ?
C7 C1 C2 O1 0.3(7) . . . . ?
C7 C1 C2 C3 -175.9(4) . . . . ?
C7 C1 C6 O3 0.1(8) . . . . ?
C7 C1 C6 C5 175.4(4) . . . . ?
O8 S2 C8 C3 -178.8(3) . . . . ?
C8 S2 O8 Sm1 -171.7(11) . . . 3_676 ?
C8 C3 C4 O2 -4.8(6) . . . . ?
C8 C3 C4 C5 178.6(4) . . . . ?
O9 S2 O8 Sm1 -55.2(11) . . . 3_676 ?
O9 S2 C8 C3 61.9(3) . . . . ?
C9 S3 O11 Sm1 37.2(5) . . . 1_665 ?
C9 C5 C6 C1 -175.7(4) . . . . ?
C9 C5 C6 O3 -0.2(8) . . . . ?
O10 S3 C9 C5 -62.2(4) . . . . ?
O10 S3 O11 Sm1 -79.8(5) . . . 1_665 ?
O11 S3 C9 C5 177.4(3) . . . . ?
O12 S3 C9 C5 58.7(4) . . . . ?
O12 S3 O11 Sm1 154.4(4) . . . 1_665 ?

_olex2_submission_special_instructions 'No special instructions were received'
