# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1422484'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;
_audit_creation_date             2015-11-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8.98 La O8.99 S2'
_chemical_formula_sum            'C10 H8.98 La O8.99 S2'
_chemical_formula_weight         476.02
_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'
La La -0.2871 2.4523 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.6665(5)
_cell_length_b                   22.7226(6)
_cell_length_c                   8.5749(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.3200(10)
_cell_angle_gamma                90
_cell_volume                     3030.22(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.917
_exptl_absorpt_coefficient_mu    3.136
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.087
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1839
_exptl_crystal_size_max          0.028
_exptl_crystal_size_mid          0.018
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6036
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.325
_diffrn_reflns_theta_min         2.991
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enraf Nonius FR590'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2044
_reflns_number_total             3080
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_refine_diff_density_max         1.713
_refine_diff_density_min         -0.988
_refine_diff_density_rms         0.153
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3080
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      0.931
_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)+(0.0631P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1071
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O8A) = Uanis(O8B) = Uanis(O8C)
3. Others
 Fixed Sof: O8A(0.33) H8AA(0.33) H8AB(0.33) O8B(0.33) H8BA(0.33) H8BB(0.33)
 O8C(0.33) H8CA(0.33) H8CB(0.33)
4.a Riding coordinates:
 O8A(H8AA,H8AB), O8B(H8BA,H8BB), O8C(H8CA,H8CB)
4.b Rotating group:
 O9(H9A,H9B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
La1 La 0.81830(2) 0.26629(2) 0.86640(5) 0.03664(15) Uani 1 1 d . . . . .
C1 C 0.8412(4) 0.0828(2) 0.5876(8) 0.0368(14) Uani 1 1 d . . . . .
C2 C 0.9045(4) 0.0570(3) 0.7435(8) 0.0424(15) Uani 1 1 d . . . . .
H2 H 0.9447 0.0805 0.8333 0.051 Uiso 1 1 calc R . . . .
C3 C 0.9072(4) -0.0026(3) 0.7636(8) 0.0451(16) Uani 1 1 d . . . . .
H3 H 0.9495 -0.0194 0.8672 0.054 Uiso 1 1 calc R . . . .
C4 C 0.8463(4) -0.0392(2) 0.6287(8) 0.0368(14) Uani 1 1 d . . . . .
C5 C 0.8492(4) 0.1011(3) 1.1483(8) 0.0387(14) Uani 1 1 d . . . . .
H5 H 0.8934 0.1182 1.2487 0.046 Uiso 1 1 calc R . . . .
C6 C 0.7878(4) 0.1360(2) 1.0211(8) 0.0361(14) Uani 1 1 d . . . . .
C7 C 0.7222(4) 0.1096(2) 0.8682(8) 0.0385(14) Uani 1 1 d . . . . .
C8 C 0.7183(4) 0.0497(2) 0.8409(8) 0.0423(15) Uani 1 1 d . . . . .
H8 H 0.6753 0.0335 0.7368 0.051 Uiso 1 1 calc R . . . .
C9 C 0.7813(4) -0.0125(2) 0.4745(8) 0.0360(14) Uani 1 1 d . . . . .
C10 C 0.7802(4) 0.0491(2) 0.4548(8) 0.0390(14) Uani 1 1 d . . . . .
H10 H 0.7383 0.0668 0.3523 0.047 Uiso 1 1 calc R . . . .
O1 O 0.8557(3) 0.18664(19) 0.7198(6) 0.0551(12) Uani 1 1 d . . . . .
O2 O 0.9260(3) 0.16772(18) 0.5425(6) 0.0523(12) Uani 1 1 d . . . . .
O3 O 0.7295(3) 0.32355(17) 0.5972(5) 0.0461(11) Uani 1 1 d . . . . .
O4 O 0.6847(3) 0.2021(2) 0.6653(6) 0.0559(13) Uani 1 1 d . . . . .
O5 O 0.5811(3) 0.1227(2) 0.5696(7) 0.0842(18) Uani 1 1 d . . . . .
O6 O 0.8971(3) 0.31616(19) 1.1800(8) 0.0665(14) Uani 1 1 d . . . . .
O7 O 0.7873(3) 0.19527(16) 1.0424(5) 0.0390(10) Uani 1 1 d . . . . .
O9 O 0.9741(3) 0.2328(2) 1.0548(6) 0.0581(13) Uani 1 1 d . . . . .
H9A H 1.0059 0.2618 1.1218 0.087 Uiso 1 1 d GR . . . .
H9B H 0.9959 0.2214 0.9865 0.087 Uiso 1 1 d GR . . . .
S1 S 0.84905(10) 0.15889(6) 0.5597(2) 0.0390(4) Uani 1 1 d . . . . .
S2 S 0.64217(11) 0.15700(7) 0.7172(3) 0.0563(5) Uani 1 1 d . . . . .
O8A O 0.9128(7) 0.3003(5) 0.7084(14) 0.0280(14) Uani 0.33 1 d . . P A 1
H8AA H 0.8650 0.3007 0.5962 0.042 Uiso 0.33 1 d R . P A 1
H8AB H 0.9390 0.2637 0.7233 0.042 Uiso 0.33 1 d R . P A 1
O8B O 0.9083(7) 0.3378(5) 0.7984(14) 0.0280(14) Uani 0.33 1 d . . P A 2
H8BA H 0.9052 0.3713 0.7336 0.042 Uiso 0.33 1 d R . P A 2
H8BB H 0.9628 0.3371 0.8975 0.042 Uiso 0.33 1 d R . P A 2
O8C O 0.8850(7) 0.3748(4) 0.9197(13) 0.0280(14) Uani 0.33 1 d . . P A 3
H8CA H 0.9248 0.3685 1.0376 0.042 Uiso 0.33 1 d R . P A 3
H8CB H 0.8386 0.3948 0.9164 0.042 Uiso 0.33 1 d R . P A 3


_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
La1 La1 4.1070(7) 7_657 ?
La1 O1 2.466(4) . ?
La1 O3 2.459(4) . ?
La1 O4 2.609(4) . ?
La1 O6 2.627(5) . ?
La1 O7 2.442(4) . ?
La1 O7 2.498(4) 7_657 ?
La1 O9 2.559(5) . ?
La1 O8A 2.714(10) . ?
La1 O8B 2.527(10) . ?
La1 O8C 2.677(9) . ?
C1 C2 1.402(8) . ?
C1 C10 1.372(8) . ?
C1 S1 1.759(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.417(9) . ?
C4 C5 1.414(8) 6 ?
C4 C9 1.412(9) . ?
C5 C4 1.414(8) 6_556 ?
C5 H5 0.9300 . ?
C5 C6 1.369(8) . ?
C6 C7 1.408(8) . ?
C6 O7 1.359(7) . ?
C7 C8 1.377(8) . ?
C7 S2 1.760(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.434(8) 6_556 ?
C9 C8 1.434(8) 6 ?
C9 C10 1.409(8) . ?
C10 H10 0.9300 . ?
O1 S1 1.464(4) . ?
O2 S1 1.449(5) . ?
O3 S1 1.457(4) 7_656 ?
O4 S2 1.460(5) . ?
O5 S2 1.442(5) . ?
O6 S2 1.486(5) 7_657 ?
O7 La1 2.498(4) 7_657 ?
O9 H9A 0.8793 . ?
O9 H9B 0.8789 . ?
S1 O3 1.457(4) 7_656 ?
S2 O6 1.486(5) 7_657 ?
O8A H8AA 0.9315 . ?
O8A H8AB 0.9314 . ?
O8B H8BA 0.9285 . ?
O8B H8BB 0.9340 . ?
O8C H8CA 0.9292 . ?
O8C H8CB 0.9264 . ?

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
O1 La1 La1 121.50(11) . 7_657 ?
O1 La1 O4 68.31(15) . . ?
O1 La1 O6 134.30(14) . . ?
O1 La1 O7 146.80(15) . 7_657 ?
O1 La1 O9 68.62(15) . . ?
O1 La1 O8A 65.0(3) . . ?
O1 La1 O8B 90.2(3) . . ?
O1 La1 O8C 124.1(3) . . ?
O3 La1 La1 109.68(10) . 7_657 ?
O3 La1 O1 96.66(14) . . ?
O3 La1 O4 72.59(14) . . ?
O3 La1 O6 121.66(14) . . ?
O3 La1 O7 82.52(14) . 7_657 ?
O3 La1 O9 140.05(14) . . ?
O3 La1 O8A 69.5(2) . . ?
O3 La1 O8B 68.6(3) . . ?
O3 La1 O8C 72.9(2) . . ?
O4 La1 La1 71.41(10) . 7_657 ?
O4 La1 O6 142.30(15) . . ?
O4 La1 O8A 114.0(2) . . ?
O4 La1 O8C 144.5(2) . . ?
O6 La1 La1 70.90(11) . 7_657 ?
O6 La1 O8A 103.6(3) . . ?
O6 La1 O8C 56.7(2) . . ?
O7 La1 La1 33.34(8) 7_657 7_657 ?
O7 La1 La1 34.21(9) . 7_657 ?
O7 La1 O1 91.30(14) . . ?
O7 La1 O3 134.38(14) . . ?
O7 La1 O4 79.99(14) 7_657 . ?
O7 La1 O4 69.00(13) . . ?
O7 La1 O6 79.49(14) . . ?
O7 La1 O6 68.93(13) 7_657 . ?
O7 La1 O7 67.55(14) . 7_657 ?
O7 La1 O9 84.39(14) . . ?
O7 La1 O9 130.23(14) 7_657 . ?
O7 La1 O8A 141.7(3) 7_657 . ?
O7 La1 O8A 150.2(3) . . ?
O7 La1 O8B 156.5(3) . . ?
O7 La1 O8B 119.5(3) 7_657 . ?
O7 La1 O8C 87.6(2) 7_657 . ?
O7 La1 O8C 135.4(2) . . ?
O9 La1 La1 109.56(11) . 7_657 ?
O9 La1 O4 128.03(14) . . ?
O9 La1 O6 65.99(14) . . ?
O9 La1 O8A 70.6(3) . . ?
O9 La1 O8C 84.9(3) . . ?
O8A La1 La1 173.3(2) . 7_657 ?
O8B La1 La1 147.7(2) . 7_657 ?
O8B La1 O4 132.7(3) . . ?
O8B La1 O6 82.7(3) . . ?
O8B La1 O9 74.4(3) . . ?
O8C La1 La1 113.5(2) . 7_657 ?
C2 C1 S1 117.6(5) . . ?
C10 C1 C2 121.0(5) . . ?
C10 C1 S1 121.2(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.1(6) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.9(6) . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 121.1(6) 6 . ?
C9 C4 C3 118.5(5) . . ?
C9 C4 C5 120.5(5) . 6 ?
C4 C5 H5 119.6 6_556 . ?
C6 C5 C4 120.8(6) . 6_556 ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.0(5) . . ?
O7 C6 C5 121.4(5) . . ?
O7 C6 C7 119.6(5) . . ?
C6 C7 S2 116.2(4) . . ?
C8 C7 C6 122.2(5) . . ?
C8 C7 S2 121.5(5) . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.3(6) . 6_556 ?
C9 C8 H8 120.3 6_556 . ?
C4 C9 C8 118.2(5) . 6 ?
C10 C9 C4 119.9(5) . . ?
C10 C9 C8 121.9(6) . 6 ?
C1 C10 C9 119.6(6) . . ?
C1 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
S1 O1 La1 150.7(3) . . ?
S1 O3 La1 156.3(3) 7_656 . ?
S2 O4 La1 128.7(2) . . ?
S2 O6 La1 127.9(3) 7_657 . ?
La1 O7 La1 112.45(14) . 7_657 ?
C6 O7 La1 123.6(3) . . ?
C6 O7 La1 116.2(3) . 7_657 ?
La1 O9 H9A 110.6 . . ?
La1 O9 H9B 110.3 . . ?
H9A O9 H9B 108.1 . . ?
O1 S1 C1 105.8(3) . . ?
O2 S1 C1 106.7(3) . . ?
O2 S1 O1 112.0(3) . . ?
O2 S1 O3 113.3(3) . 7_656 ?
O3 S1 C1 107.0(3) 7_656 . ?
O3 S1 O1 111.4(3) 7_656 . ?
O4 S2 C7 107.7(3) . . ?
O4 S2 O6 110.2(3) . 7_657 ?
O5 S2 C7 108.7(3) . . ?
O5 S2 O4 113.0(3) . . ?
O5 S2 O6 112.2(3) . 7_657 ?
O6 S2 C7 104.7(3) 7_657 . ?
La1 O8A H8AA 92.7 . . ?
La1 O8A H8AB 93.5 . . ?
H8AA O8A H8AB 107.5 . . ?
La1 O8B H8BA 143.1 . . ?
La1 O8B H8BB 105.6 . . ?
H8BA O8B H8BB 107.5 . . ?
La1 O8C H8CA 95.1 . . ?
La1 O8C H8CB 97.8 . . ?
H8CA O8C H8CB 108.1 . . ?

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
La1 O1 S1 C1 -139.4(6) . . . . ?
La1 O1 S1 O2 104.7(6) . . . . ?
La1 O1 S1 O3 -23.5(7) . . . 7_656 ?
La1 O4 S2 C7 -48.3(4) . . . . ?
La1 O4 S2 O5 -168.4(3) . . . . ?
La1 O4 S2 O6 65.3(4) . . . 7_657 ?
C1 C2 C3 C4 -0.3(10) . . . . ?
C2 C1 C10 C9 -0.4(9) . . . . ?
C2 C1 S1 O1 -53.1(5) . . . . ?
C2 C1 S1 O2 66.4(5) . . . . ?
C2 C1 S1 O3 -172.0(5) . . . 7_656 ?
C2 C3 C4 C5 179.5(6) . . . 6 ?
C2 C3 C4 C9 -1.6(9) . . . . ?
C3 C4 C9 C8 -178.1(5) . . . 6 ?
C3 C4 C9 C10 2.4(9) . . . . ?
C4 C5 C6 C7 -1.2(8) 6_556 . . . ?
C4 C5 C6 O7 176.6(5) 6_556 . . . ?
C4 C9 C10 C1 -1.4(8) . . . . ?
C5 C4 C9 C8 0.9(8) 6 . . 6 ?
C5 C4 C9 C10 -178.6(5) 6 . . . ?
C5 C6 C7 C8 -0.9(9) . . . . ?
C5 C6 C7 S2 176.4(4) . . . . ?
C5 C6 O7 La1 -101.4(5) . . . 7_657 ?
C5 C6 O7 La1 111.6(5) . . . . ?
C6 C7 C8 C9 2.1(9) . . . 6_556 ?
C6 C7 S2 O4 56.9(5) . . . . ?
C6 C7 S2 O5 179.7(5) . . . . ?
C6 C7 S2 O6 -60.3(5) . . . 7_657 ?
C7 C6 O7 La1 -70.6(6) . . . . ?
C7 C6 O7 La1 76.4(5) . . . 7_657 ?
C8 C7 S2 O4 -125.7(5) . . . . ?
C8 C7 S2 O5 -3.0(7) . . . . ?
C8 C7 S2 O6 117.0(5) . . . 7_657 ?
C8 C9 C10 C1 179.1(6) 6 . . . ?
C10 C1 C2 C3 1.3(9) . . . . ?
C10 C1 S1 O1 132.9(5) . . . . ?
C10 C1 S1 O2 -107.7(5) . . . . ?
C10 C1 S1 O3 13.9(6) . . . 7_656 ?
O7 C6 C7 C8 -178.7(6) . . . . ?
O7 C6 C7 S2 -1.4(7) . . . . ?
S1 C1 C2 C3 -172.8(5) . . . . ?
S1 C1 C10 C9 173.4(4) . . . . ?
S2 C7 C8 C9 -175.1(5) . . . 6_556 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_Compound3
_database_code_depnum_ccdc_archive 'CCDC 1422485'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 Nd O9 S2'
_chemical_formula_weight         481.53

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'
Nd Nd -0.1943 3.0179 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   17.5398(6)
_cell_length_b                   22.5802(7)
_cell_length_c                   8.5187(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.427(2)
_cell_angle_gamma                90
_cell_volume                     2967.04(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.138
_exptl_crystal_F_000             1832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    3.822
_shelx_estimated_absorpt_T_min   0.832
_shelx_estimated_absorpt_T_max   0.934
_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      293(2)
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_reflns_number            21329
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_av_R_equivalents  0.0990
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.011
_diffrn_reflns_theta_max         26.302
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3010
_reflns_number_gt                2001
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0701P)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         3010
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      0.931
_refine_ls_shift/su_max          0.001
_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
Nd1 Nd 0.81575(2) -0.26329(2) 0.36733(5) 0.03710(17) Uani 1 1 d . . . . .
S1 S 0.84741(11) 0.16141(7) 0.5541(2) 0.0366(4) Uani 1 1 d . . . . .
S2 S 0.64024(13) -0.15794(8) 0.2191(3) 0.0579(6) Uani 1 1 d . . . . .
O1 O 0.8534(3) 0.1907(2) 0.7133(6) 0.0535(13) Uani 1 1 d . . . . .
O2 O 0.9248(3) 0.1697(2) 0.5376(7) 0.0488(12) Uani 1 1 d . . . . .
O3 O 0.7678(3) 0.17876(19) 0.3951(6) 0.0464(12) Uani 1 1 d . . . . .
O4 O 0.6838(3) -0.2030(2) 0.1694(6) 0.0521(13) Uani 1 1 d . . . . .
O5 O 0.5773(4) -0.1250(3) 0.0726(9) 0.086(2) Uani 1 1 d . . . . .
O6 O 0.6028(4) -0.1855(2) 0.3296(8) 0.0667(16) Uani 1 1 d . . . . .
O7 O 0.7861(3) -0.19522(18) 0.5442(6) 0.0396(11) Uani 1 1 d . . . . .
O9 O 0.9682(4) -0.2298(3) 0.5564(7) 0.0697(18) Uani 1 1 d . . . . .
H91 H 0.9574 -0.1979 0.5880 0.104 Uiso 1 1 d R U . . .
H92 H 0.9965 -0.2214 0.4989 0.104 Uiso 1 1 d R U . . .
C1 C 0.8385(5) 0.0851(3) 0.5831(9) 0.0356(15) Uani 1 1 d . . . . .
C2 C 0.9032(5) 0.0592(3) 0.7398(9) 0.0458(18) Uani 1 1 d . . . . .
H2 H 0.9446 0.0829 0.8287 0.055 Uiso 1 1 calc R U . . .
C3 C 0.9056(5) -0.0007(3) 0.7621(10) 0.0485(19) Uani 1 1 d . . . . .
H3 H 0.9481 -0.0173 0.8675 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8446(4) -0.0376(3) 0.6276(9) 0.0373(16) Uani 1 1 d . . . . .
C5 C 0.8485(5) -0.0999(3) 0.6504(9) 0.0419(17) Uani 1 1 d . . . . .
H5 H 0.8932 -0.1168 0.7522 0.050 Uiso 1 1 calc R U . . .
C6 C 0.7866(5) -0.1354(3) 0.5228(9) 0.0382(16) Uani 1 1 d . . . . .
C7 C 0.7196(4) -0.1092(3) 0.3678(9) 0.0402(17) Uani 1 1 d . . . . .
C8 C 0.7162(5) -0.0483(3) 0.3391(10) 0.0436(17) Uani 1 1 d . . . . .
H8 H 0.6732 -0.0321 0.2335 0.052 Uiso 1 1 calc R U . . .
C9 C 0.7783(5) -0.0114(3) 0.4715(9) 0.0377(16) Uani 1 1 d . . . . .
C10 C 0.7773(4) 0.0507(3) 0.4507(9) 0.0383(16) Uani 1 1 d . . . . .
H10 H 0.7351 0.0682 0.3469 0.046 Uiso 1 1 calc R U . . .
O8A O 0.9152(12) -0.2992(9) 0.220(3) 0.052(2) Uani 0.25 1 d . . P A 1
H8A1 H 0.9452 -0.2682 0.2339 0.078 Uiso 0.25 1 d R U P A 1
H8A2 H 0.8776 -0.3015 0.1109 0.078 Uiso 0.25 1 d R U P A 1
O8B O 0.9069(6) -0.3357(4) 0.3157(13) 0.052(2) Uani 0.5 1 d . . P A 2
H8B1 H 0.9226 -0.3667 0.2821 0.078 Uiso 0.5 1 d R U P A 2
H8B2 H 0.9514 -0.3212 0.4038 0.078 Uiso 0.5 1 d R U P A 2
O8C O 0.8836(12) -0.3684(9) 0.426(3) 0.052(2) Uani 0.25 1 d . . P A 3
H8C1 H 0.8470 -0.3890 0.4410 0.078 Uiso 0.25 1 d R U P A 3
H8C2 H 0.9274 -0.3632 0.5276 0.078 Uiso 0.25 1 d R U P A 3


_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
Nd1 O7 2.377(4) . ?
Nd1 O1 2.381(5) 6 ?
Nd1 O3 2.396(4) 4_645 ?
Nd1 O7 2.432(4) 7_646 ?
Nd1 O8B 2.468(9) . ?
Nd1 O9 2.493(5) . ?
Nd1 O4 2.517(5) . ?
Nd1 O6 2.556(6) 7_646 ?
Nd1 O8C 2.594(18) . ?
Nd1 O8A 2.710(19) . ?
Nd1 Nd1 3.9692(7) 7_646 ?
Nd1 H8B2 2.6019 . ?
S1 O2 1.441(5) . ?
S1 O3 1.462(5) . ?
S1 O1 1.467(5) . ?
S1 C1 1.759(6) . ?
S2 O5 1.421(6) . ?
S2 O4 1.452(5) . ?
S2 O6 1.514(5) . ?
S2 C7 1.754(7) . ?
O1 Nd1 2.381(5) 6_556 ?
O3 Nd1 2.396(4) 4_655 ?
O6 Nd1 2.556(6) 7_646 ?
O7 C6 1.363(7) . ?
O7 Nd1 2.432(4) 7_646 ?
O9 H91 0.8220 . ?
O9 H92 0.8673 . ?
C1 C10 1.369(9) . ?
C1 C2 1.404(9) . ?
C2 C3 1.362(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(10) . ?
C3 H3 0.9300 . ?
C4 C9 1.414(9) . ?
C4 C5 1.417(9) . ?
C5 C6 1.370(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.414(10) . ?
C7 C8 1.393(9) . ?
C8 C9 1.408(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.412(9) . ?
C10 H10 0.9300 . ?
O8A H8A1 0.8498 . ?
O8A H8A2 0.8500 . ?
O8B H8B1 0.8500 . ?
O8B H8B2 0.8500 . ?
O8C H8C1 0.8501 . ?
O8C H8C2 0.8500 . ?

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
O7 Nd1 O1 96.09(17) . 6 ?
O7 Nd1 O3 136.34(17) . 4_645 ?
O1 Nd1 O3 93.94(17) 6 4_645 ?
O7 Nd1 O7 68.78(16) . 7_646 ?
O1 Nd1 O7 150.81(18) 6 7_646 ?
O3 Nd1 O7 82.27(16) 4_645 7_646 ?
O7 Nd1 O8B 153.8(3) . . ?
O1 Nd1 O8B 89.1(3) 6 . ?
O3 Nd1 O8B 68.4(3) 4_645 . ?
O7 Nd1 O8B 115.7(3) 7_646 . ?
O7 Nd1 O9 83.44(19) . . ?
O1 Nd1 O9 69.75(17) 6 . ?
O3 Nd1 O9 139.47(18) 4_645 . ?
O7 Nd1 O9 129.53(17) 7_646 . ?
O8B Nd1 O9 74.3(3) . . ?
O7 Nd1 O4 70.49(15) . . ?
O1 Nd1 O4 70.51(18) 6 . ?
O3 Nd1 O4 73.22(16) 4_645 . ?
O7 Nd1 O4 80.75(16) 7_646 . ?
O8B Nd1 O4 134.9(3) . . ?
O9 Nd1 O4 129.07(19) . . ?
O7 Nd1 O6 80.67(18) . 7_646 ?
O1 Nd1 O6 134.41(17) 6 7_646 ?
O3 Nd1 O6 119.68(17) 4_645 7_646 ?
O7 Nd1 O6 69.67(16) 7_646 7_646 ?
O8B Nd1 O6 77.4(3) . 7_646 ?
O9 Nd1 O6 64.70(17) . 7_646 ?
O4 Nd1 O6 144.57(17) . 7_646 ?
O7 Nd1 O8C 133.5(4) . . ?
O1 Nd1 O8C 120.9(5) 6 . ?
O3 Nd1 O8C 72.6(4) 4_645 . ?
O7 Nd1 O8C 85.7(5) 7_646 . ?
O9 Nd1 O8C 84.3(5) . . ?
O4 Nd1 O8C 144.5(4) . . ?
O6 Nd1 O8C 53.7(5) 7_646 . ?
O7 Nd1 O8A 150.4(5) . . ?
O1 Nd1 O8A 62.8(5) 6 . ?
O3 Nd1 O8A 69.4(5) 4_645 . ?
O7 Nd1 O8A 139.2(5) 7_646 . ?
O9 Nd1 O8A 70.2(5) . . ?
O4 Nd1 O8A 116.2(5) . . ?
O6 Nd1 O8A 99.1(5) 7_646 . ?
O7 Nd1 Nd1 34.83(10) . 7_646 ?
O1 Nd1 Nd1 126.76(14) 6 7_646 ?
O3 Nd1 Nd1 110.54(12) 4_645 7_646 ?
O7 Nd1 Nd1 33.94(10) 7_646 7_646 ?
O8B Nd1 Nd1 143.4(2) . 7_646 ?
O9 Nd1 Nd1 108.76(14) . 7_646 ?
O4 Nd1 Nd1 72.63(11) . 7_646 ?
O6 Nd1 Nd1 71.94(12) 7_646 7_646 ?
O8C Nd1 Nd1 111.5(4) . 7_646 ?
O8A Nd1 Nd1 169.9(5) . 7_646 ?
O7 Nd1 H8B2 135.5 . . ?
O1 Nd1 H8B2 86.2 6 . ?
O3 Nd1 H8B2 87.4 4_645 . ?
O7 Nd1 H8B2 122.3 7_646 . ?
O8B Nd1 H8B2 19.1 . . ?
O9 Nd1 H8B2 55.7 . . ?
O4 Nd1 H8B2 148.1 . . ?
O6 Nd1 H8B2 67.2 7_646 . ?
Nd1 Nd1 H8B2 139.0 7_646 . ?
O2 S1 O3 113.8(3) . . ?
O2 S1 O1 112.0(3) . . ?
O3 S1 O1 110.6(3) . . ?
O2 S1 C1 107.0(3) . . ?
O3 S1 C1 106.4(3) . . ?
O1 S1 C1 106.5(3) . . ?
O5 S2 O4 114.1(4) . . ?
O5 S2 O6 112.1(4) . . ?
O4 S2 O6 109.7(3) . . ?
O5 S2 C7 108.9(3) . . ?
O4 S2 C7 107.7(3) . . ?
O6 S2 C7 103.9(3) . . ?
S1 O1 Nd1 154.6(3) . 6_556 ?
S1 O3 Nd1 154.3(3) . 4_655 ?
S2 O4 Nd1 128.9(3) . . ?
S2 O6 Nd1 127.9(3) . 7_646 ?
C6 O7 Nd1 122.6(4) . . ?
C6 O7 Nd1 118.4(4) . 7_646 ?
Nd1 O7 Nd1 111.23(16) . 7_646 ?
Nd1 O9 H91 97.7 . . ?
Nd1 O9 H92 115.3 . . ?
H91 O9 H92 106.0 . . ?
C10 C1 C2 120.6(6) . . ?
C10 C1 S1 121.9(5) . . ?
C2 C1 S1 117.1(5) . . ?
C3 C2 C1 120.2(7) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.9(7) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C9 118.8(6) . . ?
C3 C4 C5 120.5(6) . . ?
C9 C4 C5 120.6(6) . . ?
C6 C5 C4 120.3(6) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
O7 C6 C5 121.8(6) . . ?
O7 C6 C7 119.0(6) . . ?
C5 C6 C7 119.2(6) . . ?
C8 C7 C6 121.7(6) . . ?
C8 C7 S2 122.7(5) . . ?
C6 C7 S2 115.6(5) . . ?
C7 C8 C9 119.4(6) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C10 121.9(6) . . ?
C8 C9 C4 118.8(6) . . ?
C10 C9 C4 119.3(6) . . ?
C1 C10 C9 120.1(6) . . ?
C1 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
Nd1 O8A H8A1 100.7 . . ?
Nd1 O8A H8A2 101.0 . . ?
H8A1 O8A H8A2 107.7 . . ?
Nd1 O8B H8B1 161.2 . . ?
Nd1 O8B H8B2 89.4 . . ?
H8B1 O8B H8B2 107.7 . . ?
Nd1 O8C H8C1 102.7 . . ?
Nd1 O8C H8C2 100.3 . . ?
H8C1 O8C H8C2 107.7 . . ?

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
O2 S1 O1 Nd1 111.6(8) . . . 6_556 ?
O3 S1 O1 Nd1 -16.5(9) . . . 6_556 ?
C1 S1 O1 Nd1 -131.8(8) . . . 6_556 ?
O2 S1 O3 Nd1 -31.2(8) . . . 4_655 ?
O1 S1 O3 Nd1 96.0(7) . . . 4_655 ?
C1 S1 O3 Nd1 -148.7(6) . . . 4_655 ?
O5 S2 O4 Nd1 169.1(4) . . . . ?
O6 S2 O4 Nd1 -64.3(5) . . . . ?
C7 S2 O4 Nd1 48.1(5) . . . . ?
O5 S2 O6 Nd1 -170.2(4) . . . 7_646 ?
O4 S2 O6 Nd1 62.0(5) . . . 7_646 ?
C7 S2 O6 Nd1 -52.9(5) . . . 7_646 ?
O2 S1 C1 C10 -107.5(6) . . . . ?
O3 S1 C1 C10 14.4(7) . . . . ?
O1 S1 C1 C10 132.5(6) . . . . ?
O2 S1 C1 C2 65.1(6) . . . . ?
O3 S1 C1 C2 -173.0(5) . . . . ?
O1 S1 C1 C2 -54.9(6) . . . . ?
C10 C1 C2 C3 -0.2(11) . . . . ?
S1 C1 C2 C3 -172.9(6) . . . . ?
C1 C2 C3 C4 1.3(11) . . . . ?
C2 C3 C4 C9 -2.8(11) . . . . ?
C2 C3 C4 C5 178.9(7) . . . . ?
C3 C4 C5 C6 176.9(7) . . . . ?
C9 C4 C5 C6 -1.5(10) . . . . ?
Nd1 O7 C6 C5 -111.9(6) . . . . ?
Nd1 O7 C6 C5 101.6(6) 7_646 . . . ?
Nd1 O7 C6 C7 70.4(7) . . . . ?
Nd1 O7 C6 C7 -76.0(6) 7_646 . . . ?
C4 C5 C6 O7 -177.0(6) . . . . ?
C4 C5 C6 C7 0.7(10) . . . . ?
O7 C6 C7 C8 179.4(6) . . . . ?
C5 C6 C7 C8 1.6(10) . . . . ?
O7 C6 C7 S2 1.3(8) . . . . ?
C5 C6 C7 S2 -176.4(5) . . . . ?
O5 S2 C7 C8 1.1(7) . . . . ?
O4 S2 C7 C8 125.2(6) . . . . ?
O6 S2 C7 C8 -118.5(6) . . . . ?
O5 S2 C7 C6 179.1(6) . . . . ?
O4 S2 C7 C6 -56.7(6) . . . . ?
O6 S2 C7 C6 59.6(6) . . . . ?
C6 C7 C8 C9 -3.2(10) . . . . ?
S2 C7 C8 C9 174.7(6) . . . . ?
C7 C8 C9 C10 -179.2(6) . . . . ?
C7 C8 C9 C4 2.4(10) . . . . ?
C3 C4 C9 C8 -178.5(6) . . . . ?
C5 C4 C9 C8 -0.1(10) . . . . ?
C3 C4 C9 C10 3.1(10) . . . . ?
C5 C4 C9 C10 -178.5(6) . . . . ?
C2 C1 C10 C9 0.6(10) . . . . ?
S1 C1 C10 C9 173.0(5) . . . . ?
C8 C9 C10 C1 179.5(7) . . . . ?
C4 C9 C10 C1 -2.1(10) . . . . ?

_refine_diff_density_max         1.893
_refine_diff_density_min         -1.164
_refine_diff_density_rms         0.167



_exptl_crystal_recrystallization_method Hydrothermal
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_Compound4
_database_code_depnum_ccdc_archive 'CCDC 1422486'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;
_audit_creation_date             2015-11-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 O9 S2 Sm'
_chemical_formula_sum            'C10 H9 O9 S2 Sm'
_chemical_formula_weight         487.64
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.5594(7)
_cell_length_b                   22.4319(9)
_cell_length_c                   8.4604(2)
_cell_angle_alpha                90
_cell_angle_beta                 118.585(2)
_cell_angle_gamma                90
_cell_volume                     2926.27(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.701
_exptl_absorpt_coefficient_mu    4.341
_exptl_absorpt_correction_T_max  0.8871
_exptl_absorpt_correction_T_min  0.7358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1880
_exptl_crystal_recrystallization_method Hydrothermal
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.013
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            24647
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.398
_diffrn_reflns_theta_min         3.028
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enraf Nonius FR590'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2043
_reflns_number_total             3002
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_refine_diff_density_max         2.484
_refine_diff_density_min         -1.205
_refine_diff_density_rms         0.174
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      0.941
_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)+(0.0560P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0993
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O8(H8A,H8B), O9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Sm1 Sm 0.81602(2) 0.26202(2) 0.87326(4) 0.03456(15) Uani 1 1 d . . . . .
C1 C 0.8367(4) 0.0877(3) 0.5824(8) 0.0338(14) Uani 1 1 d . . . . .
C2 C 0.9040(5) 0.0625(3) 0.7437(8) 0.0451(17) Uani 1 1 d . . . . .
H2 H 0.9456 0.0867 0.8322 0.054 Uiso 1 1 calc R . . . .
C3 C 0.9059(5) 0.0021(3) 0.7651(9) 0.0476(18) Uani 1 1 d . . . . .
H3 H 0.9489 -0.0146 0.8709 0.057 Uiso 1 1 calc R . . . .
C4 C 0.8439(4) -0.0360(3) 0.6300(8) 0.0355(15) Uani 1 1 d . . . . .
C5 C 0.8491(4) -0.0982(3) 0.6545(8) 0.0390(16) Uani 1 1 d . . . . .
H5 H 0.8950 -0.1147 0.7563 0.047 Uiso 1 1 calc R . . . .
C6 C 0.7134(4) 0.3654(3) 0.9711(8) 0.0355(15) Uani 1 1 d . . . . .
C7 C 0.7185(4) 0.1082(3) 0.8730(8) 0.0357(15) Uani 1 1 d . . . . .
C8 C 0.7129(4) 0.0480(3) 0.8444(8) 0.0414(16) Uani 1 1 d . . . . .
H8 H 0.6674 0.0323 0.7403 0.050 Uiso 1 1 calc R . . . .
C9 C 0.7760(4) -0.0095(3) 0.4728(8) 0.0368(15) Uani 1 1 d . . . . .
C10 C 0.7749(4) 0.0529(3) 0.4528(8) 0.0357(15) Uani 1 1 d . . . . .
H10 H 0.7314 0.0705 0.3496 0.043 Uiso 1 1 calc R . . . .
O1 O 0.8540(3) 0.1957(2) 0.7086(5) 0.0437(11) Uani 1 1 d . . . . .
O2 O 0.9224(3) 0.1707(2) 0.5307(6) 0.0454(11) Uani 1 1 d . . . . .
O3 O 0.7340(3) 0.31939(19) 0.6093(5) 0.0420(11) Uani 1 1 d . . . . .
O4 O 0.6861(3) 0.2024(2) 0.6734(5) 0.0449(12) Uani 1 1 d . . . . .
O5 O 0.5763(3) 0.1256(2) 0.5692(6) 0.0534(12) Uani 1 1 d . . . . .
O6 O 0.8970(3) 0.3142(2) 1.1704(6) 0.0471(12) Uani 1 1 d . . . . .
O7 O 0.7128(3) 0.30584(18) 0.9495(5) 0.0354(10) Uani 1 1 d . . . . .
O8 O 0.9652(3) 0.2255(3) 1.0562(6) 0.0674(17) Uani 1 1 d . . . . .
H8A H 1.0080 0.2561 1.1262 0.101 Uiso 1 1 d GR . . . .
H8B H 0.9896 0.2066 0.9865 0.101 Uiso 1 1 d GR . . . .
S1 S 0.84582(10) 0.16426(7) 0.5493(2) 0.0332(4) Uani 1 1 d . . . . .
S2 S 0.63996(11) 0.15838(8) 0.7223(2) 0.0411(4) Uani 1 1 d . . . . .
O9 O 0.9069(4) 0.3366(3) 0.8270(8) 0.0857(19) Uani 1 1 d . . . . .
H9A H 0.9027 0.3328 0.7195 0.129 Uiso 1 1 d GR . . . .
H9B H 0.9618 0.3321 0.9076 0.129 Uiso 1 1 d GR . . . .


_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 Sm1 3.8759(6) 7_657 ?
Sm1 O1 2.342(4) . ?
Sm1 O3 2.375(4) . ?
Sm1 O4 2.483(4) . ?
Sm1 O6 2.508(4) . ?
Sm1 O7 2.355(4) 7_657 ?
Sm1 O7 2.406(4) . ?
Sm1 O8 2.459(5) . ?
Sm1 O9 2.468(6) . ?
C1 C2 1.426(8) . ?
C1 C10 1.360(8) . ?
C1 S1 1.761(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.426(9) . ?
C4 C5 1.407(9) . ?
C4 C9 1.424(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(9) 4_646 ?
C6 C5 1.372(9) 4_656 ?
C6 C7 1.418(9) 7_657 ?
C6 O7 1.348(7) . ?
C7 C6 1.418(9) 7_657 ?
C7 C8 1.368(9) . ?
C7 S2 1.764(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.415(9) 6_556 ?
C9 C8 1.415(9) 6 ?
C9 C10 1.408(9) . ?
C10 H10 0.9300 . ?
O1 S1 1.466(4) . ?
O2 S1 1.435(5) . ?
O3 S1 1.449(4) 7_656 ?
O4 S2 1.456(5) . ?
O5 S2 1.442(5) . ?
O6 S2 1.479(4) 7_657 ?
O7 Sm1 2.355(4) 7_657 ?
O8 H8A 0.9804 . ?
O8 H8B 0.9767 . ?
S1 O3 1.449(4) 7_656 ?
S2 O6 1.479(4) 7_657 ?
O9 H9A 0.8817 . ?
O9 H9B 0.8808 . ?

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
O1 Sm1 Sm1 131.03(11) . 7_657 ?
O1 Sm1 O3 90.12(15) . . ?
O1 Sm1 O4 71.52(15) . . ?
O1 Sm1 O6 134.94(14) . . ?
O1 Sm1 O7 152.16(16) . . ?
O1 Sm1 O7 100.20(15) . 7_657 ?
O1 Sm1 O8 69.07(15) . . ?
O1 Sm1 O9 86.94(19) . . ?
O3 Sm1 Sm1 109.95(11) . 7_657 ?
O3 Sm1 O4 72.85(15) . . ?
O3 Sm1 O6 119.17(16) . . ?
O3 Sm1 O7 80.48(14) . . ?
O3 Sm1 O8 139.17(16) . . ?
O3 Sm1 O9 68.36(17) . . ?
O4 Sm1 Sm1 72.76(10) . 7_657 ?
O4 Sm1 O6 146.07(15) . . ?
O6 Sm1 Sm1 73.31(10) . 7_657 ?
O7 Sm1 Sm1 35.07(10) . 7_657 ?
O7 Sm1 Sm1 35.94(10) 7_657 7_657 ?
O7 Sm1 O3 136.92(15) 7_657 . ?
O7 Sm1 O4 80.66(15) . . ?
O7 Sm1 O4 71.21(14) 7_657 . ?
O7 Sm1 O6 71.29(14) . . ?
O7 Sm1 O6 81.67(15) 7_657 . ?
O7 Sm1 O7 71.01(16) 7_657 . ?
O7 Sm1 O8 132.81(14) . . ?
O7 Sm1 O8 82.67(17) 7_657 . ?
O7 Sm1 O9 152.97(17) 7_657 . ?
O7 Sm1 O9 113.12(19) . . ?
O8 Sm1 Sm1 110.14(12) . 7_657 ?
O8 Sm1 O4 127.19(18) . . ?
O8 Sm1 O6 66.55(16) . . ?
O8 Sm1 O9 75.6(2) . . ?
O9 Sm1 Sm1 141.72(15) . 7_657 ?
O9 Sm1 O4 135.26(17) . . ?
O9 Sm1 O6 75.11(17) . . ?
C2 C1 S1 116.2(5) . . ?
C10 C1 C2 121.4(6) . . ?
C10 C1 S1 122.0(5) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(6) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 121.9(6) . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 120.5(6) . . ?
C5 C4 C9 121.2(6) . . ?
C9 C4 C3 118.3(6) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.3(6) 4_646 . ?
C6 C5 H5 119.8 4_646 . ?
C5 C6 C7 118.5(6) 4_656 7_657 ?
O7 C6 C5 122.2(6) . 4_656 ?
O7 C6 C7 119.2(6) . 7_657 ?
C6 C7 S2 115.2(5) 7_657 . ?
C8 C7 C6 122.3(6) . 7_657 ?
C8 C7 S2 122.5(5) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(6) . 6_556 ?
C9 C8 H8 119.9 6_556 . ?
C8 C9 C4 117.4(6) 6 . ?
C10 C9 C4 119.0(6) . . ?
C10 C9 C8 123.6(6) . 6 ?
C1 C10 C9 120.9(6) . . ?
C1 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
S1 O1 Sm1 157.2(3) . . ?
S1 O3 Sm1 153.0(3) 7_656 . ?
S2 O4 Sm1 128.8(2) . . ?
S2 O6 Sm1 127.2(3) 7_657 . ?
Sm1 O7 Sm1 108.99(16) 7_657 . ?
C6 O7 Sm1 118.9(4) . . ?
C6 O7 Sm1 123.0(3) . 7_657 ?
Sm1 O8 H8A 115.2 . . ?
Sm1 O8 H8B 114.1 . . ?
H8A O8 H8B 103.7 . . ?
O1 S1 C1 107.5(3) . . ?
O2 S1 C1 106.0(3) . . ?
O2 S1 O1 111.6(3) . . ?
O2 S1 O3 114.5(3) . 7_656 ?
O3 S1 C1 105.9(3) 7_656 . ?
O3 S1 O1 110.8(3) 7_656 . ?
O4 S2 C7 106.8(3) . . ?
O4 S2 O6 111.1(3) . 7_657 ?
O5 S2 C7 109.0(3) . . ?
O5 S2 O4 112.8(3) . . ?
O5 S2 O6 112.5(3) . 7_657 ?
O6 S2 C7 104.0(3) 7_657 . ?
Sm1 O9 H9A 110.9 . . ?
Sm1 O9 H9B 110.6 . . ?
H9A O9 H9B 107.9 . . ?

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
Sm1 O1 S1 C1 -118.3(7) . . . . ?
Sm1 O1 S1 O2 125.8(7) . . . . ?
Sm1 O1 S1 O3 -3.1(8) . . . 7_656 ?
Sm1 O4 S2 C7 -50.4(4) . . . . ?
Sm1 O4 S2 O5 -170.2(3) . . . . ?
Sm1 O4 S2 O6 62.4(4) . . . 7_657 ?
C1 C2 C3 C4 1.2(11) . . . . ?
C2 C1 C10 C9 -0.8(9) . . . . ?
C2 C1 S1 O1 -54.8(5) . . . . ?
C2 C1 S1 O2 64.7(5) . . . . ?
C2 C1 S1 O3 -173.3(5) . . . 7_656 ?
C2 C3 C4 C5 178.4(6) . . . . ?
C2 C3 C4 C9 -3.1(10) . . . . ?
C3 C4 C5 C6 176.4(6) . . . 4_646 ?
C3 C4 C9 C8 -177.1(6) . . . 6 ?
C3 C4 C9 C10 3.0(9) . . . . ?
C4 C9 C10 C1 -1.2(9) . . . . ?
C5 C4 C9 C8 1.4(9) . . . 6 ?
C5 C4 C9 C10 -178.5(6) . . . . ?
C5 C6 O7 Sm1 -110.8(6) 4_656 . . 7_657 ?
C5 C6 O7 Sm1 105.9(6) 4_656 . . . ?
C6 C7 C8 C9 0.3(10) 7_657 . . 6_556 ?
C6 C7 S2 O4 56.5(5) 7_657 . . . ?
C6 C7 S2 O5 178.7(5) 7_657 . . . ?
C6 C7 S2 O6 -61.1(5) 7_657 . . 7_657 ?
C7 C6 O7 Sm1 70.4(7) 7_657 . . 7_657 ?
C7 C6 O7 Sm1 -72.9(6) 7_657 . . . ?
C8 C7 S2 O4 -125.4(5) . . . . ?
C8 C7 S2 O5 -3.2(6) . . . . ?
C8 C7 S2 O6 117.1(5) . . . 7_657 ?
C8 C9 C10 C1 179.0(6) 6 . . . ?
C9 C4 C5 C6 -2.0(9) . . . 4_646 ?
C10 C1 C2 C3 0.8(10) . . . . ?
C10 C1 S1 O1 132.6(5) . . . . ?
C10 C1 S1 O2 -107.9(5) . . . . ?
C10 C1 S1 O3 14.1(6) . . . 7_656 ?
S1 C1 C2 C3 -171.9(5) . . . . ?
S1 C1 C10 C9 171.5(5) . . . . ?
S2 C7 C8 C9 -177.7(5) . . . 6_556 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_Compound2
_database_code_depnum_ccdc_archive 'CCDC 1422487'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;
_audit_creation_date             2015-11-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 O9 Pr S2'
_chemical_formula_sum            'C10 H9 O9 Pr S2'
_chemical_formula_weight         478.20
_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'
Pr Pr -0.2180 2.8214 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.5597(6)
_cell_length_b                   22.6337(7)
_cell_length_c                   8.5253(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.362(2)
_cell_angle_gamma                90
_cell_volume                     2981.58(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.762
_exptl_absorpt_coefficient_mu    3.589
_exptl_absorpt_correction_T_max  0.8336
_exptl_absorpt_correction_T_min  0.7052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light green'
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.131
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_recrystallization_method Hydrothermal
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1071
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            24493
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.343
_diffrn_reflns_theta_min         3.005
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enraf Nonius FR590'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1988
_reflns_number_total             3041
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_refine_diff_density_max         1.772
_refine_diff_density_min         -1.371
_refine_diff_density_rms         0.175
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      0.953
_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)+(0.0688P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1168
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O8A) = Uanis(O8B) = Uanis(O8C)
3. Others
 Fixed Sof: O8A(0.25) H8AA(0.25) H8AB(0.25) O8B(0.45) H8BA(0.45) H8BB(0.45)
 O8C(0.3) H8CA(0.3) H8CB(0.3)
4.a Riding coordinates:
 O8A(H8AA,H8AB), O8B(H8BA,H8BB), O8C(H8CA,H8CB)
4.b Rotating group:
 O9(H9A,H9B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Pr1 Pr 0.81645(2) 0.26431(2) 0.86637(5) 0.03694(17) Uani 1 1 d . . . . .
C1 C 0.8394(4) 0.0838(3) 0.5844(8) 0.0344(15) Uani 1 1 d . . . . .
C2 C 0.9043(5) 0.0578(3) 0.7413(9) 0.0436(18) Uani 1 1 d . . . . .
H2 H 0.9460 0.0814 0.8297 0.052 Uiso 1 1 calc R . . . .
C3 C 0.9061(5) -0.0010(3) 0.7629(9) 0.0474(19) Uani 1 1 d . . . . .
H3 H 0.9478 -0.0176 0.8688 0.057 Uiso 1 1 calc R . . . .
C4 C 0.8446(4) -0.0386(3) 0.6257(8) 0.0366(16) Uani 1 1 d . . . . .
C5 C 0.8481(5) 0.1010(3) 1.1475(9) 0.0434(18) Uani 1 1 d . . . . .
H5 H 0.8926 0.1182 1.2487 0.052 Uiso 1 1 calc R . . . .
C6 C 0.7858(5) 0.1358(3) 1.0188(9) 0.0368(15) Uani 1 1 d . . . . .
C7 C 0.7209(4) 0.1093(3) 0.8674(9) 0.0413(17) Uani 1 1 d . . . . .
C8 C 0.7165(5) 0.0491(3) 0.8367(9) 0.0417(17) Uani 1 1 d . . . . .
H8 H 0.6734 0.0332 0.7311 0.050 Uiso 1 1 calc R . . . .
C9 C 0.7792(4) -0.0121(3) 0.4702(8) 0.0358(15) Uani 1 1 d . . . . .
C10 C 0.7788(4) 0.0497(3) 0.4528(9) 0.0359(15) Uani 1 1 d . . . . .
H10 H 0.7365 0.0675 0.3500 0.043 Uiso 1 1 calc R . . . .
O1 O 0.8532(3) 0.1880(2) 0.7156(6) 0.0566(14) Uani 1 1 d . . . . .
O2 O 0.9258(3) 0.1690(2) 0.5400(6) 0.0502(13) Uani 1 1 d . . . . .
O3 O 0.7691(3) 0.17758(19) 0.3971(6) 0.0457(12) Uani 1 1 d . . . . .
O4 O 0.6836(3) 0.2027(2) 0.6655(6) 0.0554(14) Uani 1 1 d . . . . .
O5 O 0.5783(4) 0.1245(2) 0.5691(9) 0.093(2) Uani 1 1 d . . . . .
O6 O 0.8979(4) 0.3147(2) 1.1758(9) 0.0766(18) Uani 1 1 d . . . . .
O7 O 0.7855(3) 0.19543(18) 1.0421(6) 0.0378(11) Uani 1 1 d . . . . .
O8A O 0.9148(11) 0.2992(8) 0.714(2) 0.0379(18) Uani 0.25 1 d . . P A 1
H8AA H 0.8598 0.2945 0.6099 0.057 Uiso 0.25 1 d R . P A 1
H8AB H 0.9449 0.2625 0.7301 0.057 Uiso 0.25 1 d R . P A 1
O8B O 0.9086(6) 0.3341(4) 0.8110(12) 0.0379(18) Uani 0.45 1 d . . P A 2
H8BA H 0.9593 0.3572 0.8460 0.057 Uiso 0.45 1 d R . P A 2
H8BB H 0.8615 0.3550 0.7196 0.057 Uiso 0.45 1 d R . P A 2
O8C O 0.8848(9) 0.3714(6) 0.9250(18) 0.0379(18) Uani 0.3 1 d . . P A 3
H8CA H 0.9168 0.3681 1.0509 0.057 Uiso 0.3 1 d R . P A 3
H8CB H 0.8371 0.3969 0.8975 0.057 Uiso 0.3 1 d R . P A 3
O9 O 0.9695(4) 0.2300(3) 1.0565(7) 0.0651(17) Uani 1 1 d . . . B 3
H9A H 1.0033 0.2594 1.1174 0.098 Uiso 1 1 d GR . . B 3
H9B H 0.9899 0.2151 0.9891 0.098 Uiso 1 1 d GR . . B 3
S1 S 0.84802(11) 0.16028(7) 0.5567(2) 0.0383(4) Uani 1 1 d . . . C 3
S2 S 0.64026(13) 0.15785(8) 0.7161(3) 0.0614(6) Uani 1 1 d . . . D 3


_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
Pr1 Pr1 4.0137(7) 7_657 ?
Pr1 O1 2.416(5) . ?
Pr1 O3 2.414(4) 7_656 ?
Pr1 O4 2.553(5) . ?
Pr1 O6 2.593(7) . ?
Pr1 O7 2.397(4) . ?
Pr1 O7 2.444(4) 7_657 ?
Pr1 O8A 2.725(17) . ?
Pr1 O8B 2.462(9) . ?
Pr1 O8C 2.645(13) . ?
Pr1 O9 2.513(5) . ?
C1 C2 1.409(9) . ?
C1 C10 1.361(9) . ?
C1 S1 1.763(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.340(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.435(9) . ?
C4 C5 1.423(9) 6 ?
C4 C9 1.411(9) . ?
C5 C4 1.423(9) 6_556 ?
C5 H5 0.9300 . ?
C5 C6 1.372(9) . ?
C6 C7 1.388(9) . ?
C6 O7 1.364(7) . ?
C7 C8 1.383(9) . ?
C7 S2 1.772(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.422(9) 6_556 ?
C9 C8 1.422(9) 6 ?
C9 C10 1.405(9) . ?
C10 H10 0.9300 . ?
O1 S1 1.457(5) . ?
O2 S1 1.452(5) . ?
O3 Pr1 2.414(4) 7_656 ?
O3 S1 1.460(5) . ?
O4 S2 1.452(5) . ?
O5 S2 1.425(6) . ?
O6 S2 1.506(6) 7_657 ?
O7 Pr1 2.444(4) 7_657 ?
O8A H8AA 0.9572 . ?
O8A H8AB 0.9577 . ?
O8B H8BA 0.9504 . ?
O8B H8BB 0.9501 . ?
O8C H8CA 0.9490 . ?
O8C H8CB 0.9506 . ?
O9 H9A 0.8768 . ?
O9 H9B 0.8760 . ?
S2 O6 1.507(6) 7_657 ?

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
O1 Pr1 Pr1 124.12(14) . 7_657 ?
O1 Pr1 O4 69.08(18) . . ?
O1 Pr1 O6 134.30(16) . . ?
O1 Pr1 O7 149.05(18) . 7_657 ?
O1 Pr1 O8A 64.1(4) . . ?
O1 Pr1 O8B 89.5(3) . . ?
O1 Pr1 O8C 122.9(4) . . ?
O1 Pr1 O9 69.44(17) . . ?
O3 Pr1 Pr1 110.09(12) 7_656 7_657 ?
O3 Pr1 O1 95.72(16) 7_656 . ?
O3 Pr1 O4 72.95(15) 7_656 . ?
O3 Pr1 O6 120.36(17) 7_656 . ?
O3 Pr1 O7 82.37(16) 7_656 7_657 ?
O3 Pr1 O8A 69.7(4) 7_656 . ?
O3 Pr1 O8B 69.4(2) 7_656 . ?
O3 Pr1 O8C 72.7(3) 7_656 . ?
O3 Pr1 O9 140.42(18) 7_656 . ?
O4 Pr1 Pr1 72.56(12) . 7_657 ?
O4 Pr1 O6 144.01(18) . . ?
O4 Pr1 O8A 115.0(4) . . ?
O4 Pr1 O8C 144.6(3) . . ?
O6 Pr1 Pr1 71.45(13) . 7_657 ?
O6 Pr1 O8A 100.9(4) . . ?
O6 Pr1 O8C 54.8(3) . . ?
O7 Pr1 Pr1 34.36(10) . 7_657 ?
O7 Pr1 Pr1 33.61(9) 7_657 7_657 ?
O7 Pr1 O1 93.72(17) . . ?
O7 Pr1 O3 135.27(16) . 7_656 ?
O7 Pr1 O4 80.98(16) 7_657 . ?
O7 Pr1 O4 70.01(15) . . ?
O7 Pr1 O6 69.18(16) 7_657 . ?
O7 Pr1 O6 80.19(17) . . ?
O7 Pr1 O7 67.98(16) . 7_657 ?
O7 Pr1 O8A 150.4(4) . . ?
O7 Pr1 O8A 140.4(4) 7_657 . ?
O7 Pr1 O8B 118.0(3) 7_657 . ?
O7 Pr1 O8B 154.4(2) . . ?
O7 Pr1 O8C 134.1(3) . . ?
O7 Pr1 O8C 86.2(3) 7_657 . ?
O7 Pr1 O9 129.08(16) 7_657 . ?
O7 Pr1 O9 83.48(18) . . ?
O8A Pr1 Pr1 171.3(4) . 7_657 ?
O8B Pr1 Pr1 145.6(2) . 7_657 ?
O8B Pr1 O4 134.1(2) . . ?
O8B Pr1 O6 79.5(3) . . ?
O8C Pr1 Pr1 112.0(3) . 7_657 ?
O9 Pr1 Pr1 108.42(13) . 7_657 ?
O9 Pr1 O4 128.37(18) . . ?
O9 Pr1 O6 64.89(16) . . ?
O9 Pr1 O8C 84.9(3) . . ?
C2 C1 S1 117.1(5) . . ?
C10 C1 C2 120.6(6) . . ?
C10 C1 S1 122.0(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(6) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(6) . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.9(6) 6 . ?
C9 C4 C3 118.4(6) . . ?
C9 C4 C5 120.7(6) . 6 ?
C4 C5 H5 120.1 6_556 . ?
C6 C5 C4 119.9(6) . 6_556 ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 119.1(6) . . ?
O7 C6 C5 120.6(6) . . ?
O7 C6 C7 120.3(6) . . ?
C6 C7 S2 115.3(5) . . ?
C8 C7 C6 123.3(6) . . ?
C8 C7 S2 121.3(5) . . ?
C7 C8 H8 120.8 . . ?
C7 C8 C9 118.5(6) . 6_556 ?
C9 C8 H8 120.8 6_556 . ?
C4 C9 C8 118.5(6) . 6 ?
C10 C9 C4 118.9(6) . . ?
C10 C9 C8 122.6(6) . 6 ?
C1 C10 C9 120.9(6) . . ?
C1 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
S1 O1 Pr1 152.7(3) . . ?
S1 O3 Pr1 155.3(3) . 7_656 ?
S2 O4 Pr1 128.6(3) . . ?
S2 O6 Pr1 127.8(3) 7_657 . ?
Pr1 O7 Pr1 112.03(16) . 7_657 ?
C6 O7 Pr1 122.3(4) . . ?
C6 O7 Pr1 118.0(4) . 7_657 ?
Pr1 O8A H8AA 79.7 . . ?
Pr1 O8A H8AB 96.5 . . ?
H8AA O8A H8AB 106.5 . . ?
Pr1 O8B H8BA 153.7 . . ?
Pr1 O8B H8BB 94.7 . . ?
H8BA O8B H8BB 107.7 . . ?
Pr1 O8C H8CA 96.5 . . ?
Pr1 O8C H8CB 104.0 . . ?
H8CA O8C H8CB 107.7 . . ?
Pr1 O9 H9A 111.3 . . ?
Pr1 O9 H9B 109.9 . . ?
H9A O9 H9B 108.0 . . ?
O1 S1 C1 105.7(3) . . ?
O1 S1 O3 111.3(3) . . ?
O2 S1 C1 106.9(3) . . ?
O2 S1 O1 112.8(3) . . ?
O2 S1 O3 113.1(3) . . ?
O3 S1 C1 106.5(3) . . ?
O4 S2 C7 107.4(3) . . ?
O4 S2 O6 110.0(3) . 7_657 ?
O5 S2 C7 108.9(3) . . ?
O5 S2 O4 113.5(4) . . ?
O5 S2 O6 112.4(4) . 7_657 ?
O6 S2 C7 104.1(4) 7_657 . ?

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
Pr1 O1 S1 C1 -138.1(7) . . . . ?
Pr1 O1 S1 O2 105.5(8) . . . . ?
Pr1 O1 S1 O3 -22.9(9) . . . . ?
Pr1 O3 S1 C1 -149.8(7) 7_656 . . . ?
Pr1 O3 S1 O1 95.5(7) 7_656 . . . ?
Pr1 O3 S1 O2 -32.7(8) 7_656 . . . ?
Pr1 O4 S2 C7 -48.3(5) . . . . ?
Pr1 O4 S2 O5 -168.8(4) . . . . ?
Pr1 O4 S2 O6 64.4(5) . . . 7_657 ?
C1 C2 C3 C4 2.4(12) . . . . ?
C2 C1 C10 C9 0.2(10) . . . . ?
C2 C1 S1 O1 -55.2(6) . . . . ?
C2 C1 S1 O2 65.2(6) . . . . ?
C2 C1 S1 O3 -173.6(5) . . . . ?
C2 C3 C4 C5 178.3(7) . . . 6 ?
C2 C3 C4 C9 -3.2(11) . . . . ?
C3 C4 C9 C8 -177.8(6) . . . 6 ?
C3 C4 C9 C10 2.4(10) . . . . ?
C4 C5 C6 C7 -1.2(10) 6_556 . . . ?
C4 C5 C6 O7 176.4(6) 6_556 . . . ?
C4 C9 C10 C1 -1.0(10) . . . . ?
C5 C4 C9 C8 0.7(10) 6 . . 6 ?
C5 C4 C9 C10 -179.1(6) 6 . . . ?
C5 C6 C7 C8 -1.3(11) . . . . ?
C5 C6 C7 S2 176.4(5) . . . . ?
C5 C6 O7 Pr1 -101.2(6) . . . 7_657 ?
C5 C6 O7 Pr1 111.8(6) . . . . ?
C6 C7 C8 C9 2.8(11) . . . 6_556 ?
C6 C7 S2 O4 57.1(6) . . . . ?
C6 C7 S2 O5 -179.6(6) . . . . ?
C6 C7 S2 O6 -59.5(6) . . . 7_657 ?
C7 C6 O7 Pr1 76.3(7) . . . 7_657 ?
C7 C6 O7 Pr1 -70.7(7) . . . . ?
C8 C7 S2 O4 -125.1(6) . . . . ?
C8 C7 S2 O5 -1.8(8) . . . . ?
C8 C7 S2 O6 118.3(6) . . . 7_657 ?
C8 C9 C10 C1 179.2(7) 6 . . . ?
C10 C1 C2 C3 -0.9(11) . . . . ?
C10 C1 S1 O1 132.0(6) . . . . ?
C10 C1 S1 O2 -107.6(6) . . . . ?
C10 C1 S1 O3 13.6(7) . . . . ?
O7 C6 C7 C8 -178.9(6) . . . . ?
O7 C6 C7 S2 -1.1(9) . . . . ?
S1 C1 C2 C3 -173.9(6) . . . . ?
S1 C1 C10 C9 172.8(5) . . . . ?
S2 C7 C8 C9 -174.9(5) . . . 6_556 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_Compound8
_database_code_depnum_ccdc_archive 'CCDC 1426613'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;
_audit_creation_date             2015-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 N2 O8 S2 Sm, 3(H2 O)'
_chemical_formula_sum            'C22 H21 N2 O11 S2 Sm'
_chemical_formula_weight         703.88
_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'
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'
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      triclinic
_space_group_IT_number           2
_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                   9.2483(14)
_cell_length_b                   11.9016(15)
_cell_length_c                   12.6880(19)
_cell_angle_alpha                106.599(8)
_cell_angle_beta                 110.207(7)
_cell_angle_gamma                99.271(9)
_cell_volume                     1202.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.47
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.682
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0593 before and 0.0333 after correction.
The Ratio of minimum to maximum transmission is 0.9077.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             698
_exptl_crystal_recrystallization_method Hydrothermal
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14779
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.464
_diffrn_reflns_theta_min         1.865
_diffrn_ambient_temperature      293
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4463
_reflns_number_total             4837
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4837
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0222
_refine_ls_restrained_S_all      1.071
_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)+(0.0197P)²+1.8190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0529
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O8-H8A = O8-H8B
 0.84 with sigma of 0.02
3.a Free rotating group:
 O9(H9A,H9B), O10(H10A,H10B), O11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C1 C 0.6932(3) 0.3417(2) 0.6417(3) 0.0170(6) Uani 1 1 d . . . . .
C2 C 0.7508(3) 0.2718(3) 0.7059(3) 0.0200(6) Uani 1 1 d . . . . .
H2 H 0.8589 0.2962 0.7588 0.024 Uiso 1 1 calc R . . . .
C3 C 0.6466(3) 0.1628(2) 0.6922(3) 0.0181(6) Uani 1 1 d . . . . .
C4 C 0.6991(4) 0.0910(3) 0.7617(3) 0.0212(6) Uani 1 1 d . . . . .
H4 H 0.8057 0.1143 0.8173 0.025 Uiso 1 1 calc R . . . .
C5 C 0.5928(4) -0.0127(3) 0.7468(3) 0.0204(6) Uani 1 1 d . . . . .
C6 C 0.4316(4) -0.0508(3) 0.6622(3) 0.0254(7) Uani 1 1 d . . . . .
H6 H 0.3612 -0.1218 0.6528 0.030 Uiso 1 1 calc R . . . .
C7 C 0.3788(4) 0.0162(3) 0.5942(3) 0.0246(7) Uani 1 1 d . . . . .
H7 H 0.2722 -0.0099 0.5383 0.030 Uiso 1 1 calc R . . . .
C8 C 0.4833(3) 0.1253(2) 0.6070(3) 0.0179(6) Uani 1 1 d . . . . .
C9 C 0.4278(3) 0.1982(2) 0.5405(3) 0.0176(6) Uani 1 1 d . . . . .
H9 H 0.3222 0.1717 0.4826 0.021 Uiso 1 1 calc R . . . .
C10 C 0.5278(3) 0.3077(2) 0.5602(2) 0.0162(6) Uani 1 1 d . . . . .
C11 C 0.8854(4) 0.6739(3) 0.4423(3) 0.0310(7) Uani 1 1 d . . . . .
H11 H 0.9247 0.6437 0.5031 0.037 Uiso 1 1 calc R . . . .
C12 C 0.9826(4) 0.7804(3) 0.4476(4) 0.0412(9) Uani 1 1 d . . . . .
H12 H 1.0841 0.8191 0.5107 0.049 Uiso 1 1 calc R . . . .
C13 C 0.9279(5) 0.8268(3) 0.3604(4) 0.0396(9) Uani 1 1 d . . . . .
H13 H 0.9915 0.8976 0.3633 0.047 Uiso 1 1 calc R . . . .
C14 C 0.7746(4) 0.7672(3) 0.2658(3) 0.0297(7) Uani 1 1 d . . . . .
C15 C 0.7057(5) 0.8122(3) 0.1730(4) 0.0419(9) Uani 1 1 d . . . . .
H15 H 0.7658 0.8823 0.1720 0.050 Uiso 1 1 calc R . . . .
C16 C 0.5558(5) 0.7556(4) 0.0869(4) 0.0427(9) Uani 1 1 d . . . . .
H16 H 0.5128 0.7883 0.0287 0.051 Uiso 1 1 calc R . . . .
C17 C 0.4610(4) 0.6457(3) 0.0832(3) 0.0326(8) Uani 1 1 d . . . . .
C18 C 0.3047(5) 0.5828(4) -0.0054(3) 0.0443(10) Uani 1 1 d . . . . .
H18 H 0.2557 0.6141 -0.0633 0.053 Uiso 1 1 calc R . . . .
C19 C 0.2251(5) 0.4760(4) -0.0063(3) 0.0427(9) Uani 1 1 d . . . . .
H19 H 0.1221 0.4329 -0.0658 0.051 Uiso 1 1 calc R . . . .
C20 C 0.2986(4) 0.4314(3) 0.0824(3) 0.0336(8) Uani 1 1 d . . . . .
H20 H 0.2436 0.3571 0.0795 0.040 Uiso 1 1 calc R . . . .
C21 C 0.5264(4) 0.5964(3) 0.1715(3) 0.0220(6) Uani 1 1 d . . . . .
C22 C 0.6845(4) 0.6597(3) 0.2662(3) 0.0227(6) Uani 1 1 d . . . . .
Sm1 Sm 0.54616(2) 0.43279(2) 0.35928(2) 0.01558(5) Uani 1 1 d . . . . .
N1 N 0.7403(3) 0.6143(2) 0.3548(2) 0.0210(5) Uani 1 1 d . . . . .
N2 N 0.4440(3) 0.4906(2) 0.1712(2) 0.0240(6) Uani 1 1 d . . . . .
O1 O 0.9791(2) 0.49809(19) 0.7329(2) 0.0253(5) Uani 1 1 d . . . . .
O2 O 0.7481(2) 0.57681(18) 0.70209(19) 0.0221(4) Uani 1 1 d . . . . .
O3 O 0.7928(2) 0.46381(19) 0.53024(19) 0.0219(4) Uani 1 1 d . . . . .
O4 O 0.4108(4) 0.0687(2) 0.0717(2) 0.0441(7) Uani 1 1 d . . . . .
O5 O 0.4177(3) 0.22660(19) 0.2418(2) 0.0330(5) Uani 1 1 d . . . . .
O6 O 0.1727(3) 0.0634(2) 0.1107(3) 0.0463(7) Uani 1 1 d . . . . .
O7 O 0.4746(2) 0.38621(17) 0.50813(17) 0.0162(4) Uani 1 1 d . . . . .
O8 O 0.7303(3) 0.3611(2) 0.2760(2) 0.0355(6) Uani 1 1 d D . . . .
H8A H 0.811(4) 0.411(3) 0.286(4) 0.053 Uiso 1 1 d DR . . . .
H8B H 0.726(5) 0.291(2) 0.237(4) 0.053 Uiso 1 1 d DR . . . .
O9 O 0.7585(4) 0.1485(3) 0.1610(4) 0.0738(11) Uani 1 1 d . . . . .
H9A H 0.8130 0.1566 0.1206 0.111 Uiso 1 1 d G . . . .
H9B H 0.6656 0.0995 0.1142 0.111 Uiso 1 1 d G . . . .
S1 S 0.81453(8) 0.47974(6) 0.65463(6) 0.01701(14) Uani 1 1 d . . . . .
S2 S 0.34525(9) 0.09727(6) 0.16014(7) 0.02241(16) Uani 1 1 d . . . . .
O10 O 0.9739(4) 0.2206(3) 0.0697(4) 0.0721(10) Uani 1 1 d . . . . .
H10A H 0.9976 0.1536 0.0580 0.108 Uiso 1 1 d G . . . .
H10B H 1.0515 0.2767 0.1298 0.108 Uiso 1 1 d G . . . .
O11 O 1.0336(7) 0.0795(6) 0.2942(6) 0.1261(18) Uani 1 1 d . . . . .
H11A H 1.0740 0.1380 0.2780 0.189 Uiso 1 1 d G . . . .
H11B H 0.9338 0.0706 0.2737 0.189 Uiso 1 1 d G . . . .


_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
C1 C2 1.367(4) . ?
C1 C10 1.429(4) . ?
C1 S1 1.764(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.412(4) . ?
C3 C4 1.419(4) . ?
C3 C8 1.424(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(4) . ?
C5 C6 1.407(4) . ?
C5 S2 1.770(3) 2_656 ?
C6 H6 0.9300 . ?
C6 C7 1.358(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.418(4) . ?
C8 C9 1.412(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(4) . ?
C10 O7 1.352(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.400(5) . ?
C11 N1 1.323(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.356(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.403(5) . ?
C14 C15 1.426(5) . ?
C14 C22 1.412(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.342(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.431(5) . ?
C17 C18 1.400(5) . ?
C17 C21 1.410(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.357(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.393(5) . ?
C20 H20 0.9300 . ?
C20 N2 1.330(4) . ?
C21 C22 1.436(4) . ?
C21 N2 1.360(4) . ?
C22 N1 1.364(4) . ?
Sm1 Sm1 3.9143(6) 2_666 ?
Sm1 N1 2.605(2) . ?
Sm1 N2 2.579(3) . ?
Sm1 O2 2.532(2) 2_666 ?
Sm1 O3 2.429(2) . ?
Sm1 O5 2.324(2) . ?
Sm1 O7 2.3780(19) . ?
Sm1 O7 2.4070(19) 2_666 ?
Sm1 O8 2.437(2) . ?
O1 S1 1.441(2) . ?
O2 Sm1 2.532(2) 2_666 ?
O2 S1 1.470(2) . ?
O3 S1 1.471(2) . ?
O4 S2 1.436(3) . ?
O5 S2 1.473(2) . ?
O6 S2 1.435(3) . ?
O7 Sm1 2.4070(19) 2_666 ?
O8 H8A 0.825(19) . ?
O8 H8B 0.826(19) . ?
O9 H9A 0.8466 . ?
O9 H9B 0.8481 . ?
S2 C5 1.770(3) 2_656 ?
O10 H10A 0.8464 . ?
O10 H10B 0.8474 . ?
O11 H11A 0.8473 . ?
O11 H11B 0.8471 . ?

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
C2 C1 C10 121.6(3) . . ?
C2 C1 S1 123.1(2) . . ?
C10 C1 S1 115.4(2) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 122.0(3) . . ?
C2 C3 C8 118.7(3) . . ?
C4 C3 C8 119.3(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 S2 120.0(2) . 2_656 ?
C6 C5 S2 118.8(2) . 2_656 ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C3 118.5(3) . . ?
C9 C8 C3 119.9(3) . . ?
C9 C8 C7 121.6(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C1 118.7(2) . . ?
O7 C10 C1 118.8(2) . . ?
O7 C10 C9 122.4(3) . . ?
C12 C11 H11 118.4 . . ?
N1 C11 H11 118.4 . . ?
N1 C11 C12 123.1(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.5(3) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 123.0(3) . . ?
C13 C14 C22 117.5(3) . . ?
C22 C14 C15 119.4(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 123.1(3) . . ?
C18 C17 C21 117.5(3) . . ?
C21 C17 C16 119.4(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 118.6 . . ?
N2 C20 C19 122.7(3) . . ?
N2 C20 H20 118.6 . . ?
C17 C21 C22 119.4(3) . . ?
N2 C21 C17 122.2(3) . . ?
N2 C21 C22 118.3(3) . . ?
C14 C22 C21 119.3(3) . . ?
N1 C22 C14 122.5(3) . . ?
N1 C22 C21 118.1(3) . . ?
N1 Sm1 Sm1 106.26(6) . 2_666 ?
N2 Sm1 Sm1 122.51(6) . 2_666 ?
N2 Sm1 N1 63.47(8) . . ?
O2 Sm1 Sm1 68.42(5) 2_666 2_666 ?
O2 Sm1 N1 119.04(7) 2_666 . ?
O2 Sm1 N2 70.20(7) 2_666 . ?
O3 Sm1 Sm1 75.94(5) . 2_666 ?
O3 Sm1 N1 78.71(7) . . ?
O3 Sm1 N2 140.89(7) . . ?
O3 Sm1 O2 143.30(7) . 2_666 ?
O3 Sm1 O8 73.44(8) . . ?
O5 Sm1 Sm1 116.46(6) . 2_666 ?
O5 Sm1 N1 137.25(8) . . ?
O5 Sm1 N2 90.94(8) . . ?
O5 Sm1 O2 77.63(8) . 2_666 ?
O5 Sm1 O3 112.21(8) . . ?
O5 Sm1 O7 84.95(8) . . ?
O5 Sm1 O7 144.26(8) . 2_666 ?
O5 Sm1 O8 74.69(9) . . ?
O7 Sm1 Sm1 34.87(4) 2_666 2_666 ?
O7 Sm1 Sm1 35.36(4) . 2_666 ?
O7 Sm1 N1 75.16(7) 2_666 . ?
O7 Sm1 N1 136.06(7) . . ?
O7 Sm1 N2 143.86(7) . . ?
O7 Sm1 N2 94.37(7) 2_666 . ?
O7 Sm1 O2 73.86(7) . 2_666 ?
O7 Sm1 O2 71.12(6) 2_666 2_666 ?
O7 Sm1 O3 72.07(7) . . ?
O7 Sm1 O3 84.78(7) 2_666 . ?
O7 Sm1 O7 70.22(7) . 2_666 ?
O7 Sm1 O8 141.02(8) 2_666 . ?
O7 Sm1 O8 128.99(8) . . ?
O8 Sm1 Sm1 149.34(7) . 2_666 ?
O8 Sm1 N1 69.20(8) . . ?
O8 Sm1 N2 83.69(9) . . ?
O8 Sm1 O2 141.31(8) . 2_666 ?
C11 N1 C22 117.7(3) . . ?
C11 N1 Sm1 122.9(2) . . ?
C22 N1 Sm1 118.92(19) . . ?
C20 N2 C21 118.1(3) . . ?
C20 N2 Sm1 121.3(2) . . ?
C21 N2 Sm1 119.56(19) . . ?
S1 O2 Sm1 127.07(11) . 2_666 ?
S1 O3 Sm1 127.82(12) . . ?
S2 O5 Sm1 174.33(16) . . ?
C10 O7 Sm1 115.38(16) . 2_666 ?
C10 O7 Sm1 124.57(16) . . ?
Sm1 O7 Sm1 109.78(7) . 2_666 ?
Sm1 O8 H8A 119(3) . . ?
Sm1 O8 H8B 130(3) . . ?
H8A O8 H8B 110(4) . . ?
H9A O9 H9B 109.6 . . ?
O1 S1 C1 109.28(13) . . ?
O1 S1 O2 112.70(13) . . ?
O1 S1 O3 112.47(13) . . ?
O2 S1 C1 106.26(13) . . ?
O2 S1 O3 110.78(12) . . ?
O3 S1 C1 104.85(13) . . ?
O4 S2 C5 106.89(15) . 2_656 ?
O4 S2 O5 111.00(15) . . ?
O5 S2 C5 105.00(14) . 2_656 ?
O6 S2 C5 106.92(14) . 2_656 ?
O6 S2 O4 114.43(18) . . ?
O6 S2 O5 111.93(16) . . ?
H10A O10 H10B 109.5 . . ?
H11A O11 H11B 109.6 . . ?

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
C1 C2 C3 C4 -176.6(3) . . . . ?
C1 C2 C3 C8 2.5(4) . . . . ?
C1 C10 O7 Sm1 -71.6(3) . . . 2_666 ?
C1 C10 O7 Sm1 69.8(3) . . . . ?
C2 C1 C10 C9 -4.4(4) . . . . ?
C2 C1 C10 O7 173.7(3) . . . . ?
C2 C1 S1 O1 4.8(3) . . . . ?
C2 C1 S1 O2 -117.0(3) . . . . ?
C2 C1 S1 O3 125.6(3) . . . . ?
C2 C3 C4 C5 178.7(3) . . . . ?
C2 C3 C8 C7 -179.5(3) . . . . ?
C2 C3 C8 C9 -1.5(4) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C3 C4 C5 S2 -176.1(2) . . . 2_656 ?
C3 C8 C9 C10 -2.6(4) . . . . ?
C4 C3 C8 C7 -0.4(4) . . . . ?
C4 C3 C8 C9 177.6(3) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C6 C7 C8 C3 0.8(5) . . . . ?
C6 C7 C8 C9 -177.3(3) . . . . ?
C7 C8 C9 C10 175.4(3) . . . . ?
C8 C3 C4 C5 -0.4(4) . . . . ?
C8 C9 C10 C1 5.4(4) . . . . ?
C8 C9 C10 O7 -172.6(3) . . . . ?
C9 C10 O7 Sm1 106.4(3) . . . 2_666 ?
C9 C10 O7 Sm1 -112.2(3) . . . . ?
C10 C1 C2 C3 0.4(4) . . . . ?
C10 C1 S1 O1 -176.2(2) . . . . ?
C10 C1 S1 O2 62.0(2) . . . . ?
C10 C1 S1 O3 -55.4(2) . . . . ?
C11 C12 C13 C14 -0.1(6) . . . . ?
C12 C11 N1 C22 0.1(5) . . . . ?
C12 C11 N1 Sm1 -172.1(3) . . . . ?
C12 C13 C14 C15 177.6(4) . . . . ?
C12 C13 C14 C22 -0.4(5) . . . . ?
C13 C14 C15 C16 -177.0(4) . . . . ?
C13 C14 C22 C21 179.5(3) . . . . ?
C13 C14 C22 N1 0.8(5) . . . . ?
C14 C15 C16 C17 -1.7(6) . . . . ?
C14 C22 N1 C11 -0.7(4) . . . . ?
C14 C22 N1 Sm1 171.8(2) . . . . ?
C15 C14 C22 C21 1.3(5) . . . . ?
C15 C14 C22 N1 -177.3(3) . . . . ?
C15 C16 C17 C18 -179.4(4) . . . . ?
C15 C16 C17 C21 0.0(6) . . . . ?
C16 C17 C18 C19 176.9(4) . . . . ?
C16 C17 C21 C22 2.4(5) . . . . ?
C16 C17 C21 N2 -178.3(3) . . . . ?
C17 C18 C19 C20 1.3(6) . . . . ?
C17 C21 C22 C14 -3.0(4) . . . . ?
C17 C21 C22 N1 175.7(3) . . . . ?
C17 C21 N2 C20 1.6(4) . . . . ?
C17 C21 N2 Sm1 -166.8(2) . . . . ?
C18 C17 C21 C22 -178.2(3) . . . . ?
C18 C17 C21 N2 1.1(5) . . . . ?
C18 C19 C20 N2 1.6(6) . . . . ?
C19 C20 N2 C21 -3.0(5) . . . . ?
C19 C20 N2 Sm1 165.2(3) . . . . ?
C21 C17 C18 C19 -2.5(6) . . . . ?
C21 C22 N1 C11 -179.3(3) . . . . ?
C21 C22 N1 Sm1 -6.8(3) . . . . ?
C22 C14 C15 C16 1.0(6) . . . . ?
C22 C21 N2 C20 -179.1(3) . . . . ?
C22 C21 N2 Sm1 12.5(4) . . . . ?
Sm1 O2 S1 C1 -41.69(18) 2_666 . . . ?
Sm1 O2 S1 O1 -161.34(13) 2_666 . . . ?
Sm1 O2 S1 O3 71.65(16) 2_666 . . . ?
Sm1 O3 S1 C1 62.33(17) . . . . ?
Sm1 O3 S1 O1 -179.03(13) . . . . ?
Sm1 O3 S1 O2 -51.90(17) . . . . ?
N1 C11 C12 C13 0.3(6) . . . . ?
N2 C21 C22 C14 177.6(3) . . . . ?
N2 C21 C22 N1 -3.7(4) . . . . ?
S1 C1 C2 C3 179.3(2) . . . . ?
S1 C1 C10 C9 176.6(2) . . . . ?
S1 C1 C10 O7 -5.4(3) . . . . ?
S2 C5 C6 C7 176.5(3) 2_656 . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_Compound9
_database_code_depnum_ccdc_archive 'CCDC 1426614'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;
_audit_creation_date             2015-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C52 H46 La2 N4 O16 S4, 3(O)'
_chemical_formula_sum            'C52 H46 La2 N4 O19 S4'
_chemical_formula_weight         1436.99
_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'
La La -0.2871 2.4523 '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'
S S 0.1246 0.1234 '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                   10.7422(4)
_cell_length_b                   17.1435(7)
_cell_length_c                   14.8397(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.001(2)
_cell_angle_gamma                90
_cell_volume                     2729.12(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.777
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_description       prism
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1432
_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  ?
_diffrn_reflns_av_unetI/netI     0.1469
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            5568
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.349
_diffrn_reflns_theta_min         2.995
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3032
_reflns_number_total             5568
_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_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_diff_density_max         2.281
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.172
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5568
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1457
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.028
_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)+(0.0521P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1364
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: O1AA(0.5)
3.a Rotating group:
 O8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C10(H10), C18(H18), C20(H20), C22(H22), C23(H23),
 C25(H25)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C1 C 0.1911(7) 0.2041(4) 0.1040(5) 0.0322(19) Uani 1 1 d . . . . .
H1 H 0.1718 0.1709 0.1507 0.039 Uiso 1 1 calc R . . . .
C2 C 0.1915(8) 0.2840(4) 0.1222(5) 0.037(2) Uani 1 1 d . . . . .
C3 C 0.2210(9) 0.3342(4) 0.0552(6) 0.044(2) Uani 1 1 d . . . . .
C4 C 0.2517(8) 0.3028(4) -0.0303(5) 0.038(2) Uani 1 1 d . . . . .
C5 C 0.2845(9) 0.3502(5) -0.1047(6) 0.050(3) Uani 1 1 d . . . . .
H5 H 0.2907 0.4040 -0.0973 0.060 Uiso 1 1 calc R . . . .
C6 C 0.3061(9) 0.3189(5) -0.1838(6) 0.052(3) Uani 1 1 d . . . . .
H6 H 0.3249 0.3520 -0.2309 0.063 Uiso 1 1 calc R . . . .
C7 C 0.3018(8) 0.2374(4) -0.2004(5) 0.036(2) Uani 1 1 d . . . . .
C8 C 0.3185(8) 0.2037(5) -0.2851(5) 0.040(2) Uani 1 1 d . . . . .
C9 C 0.3190(8) 0.1228(5) -0.2927(5) 0.037(2) Uani 1 1 d . . . . .
C10 C 0.2944(8) 0.0794(5) -0.2161(5) 0.037(2) Uani 1 1 d . . . . .
H10 H 0.2942 0.0254 -0.2214 0.044 Uiso 1 1 calc R . . . .
C11 C 0.2743(8) 0.1883(4) -0.1283(5) 0.0308(19) Uani 1 1 d . . . . .
C12 C 0.2476(7) 0.2204(4) -0.0433(5) 0.0307(19) Uani 1 1 d . . . . .
C13 C 0.1593(9) 0.3088(5) 0.2167(5) 0.051(3) Uani 1 1 d . . . . .
H13A H 0.1468 0.2633 0.2529 0.077 Uiso 1 1 calc GR . . . .
H13B H 0.0844 0.3394 0.2133 0.077 Uiso 1 1 calc GR . . . .
H13C H 0.2264 0.3393 0.2437 0.077 Uiso 1 1 calc GR . . . .
C14 C 0.2214(10) 0.4218(4) 0.0703(6) 0.062(3) Uani 1 1 d . . . . .
H14A H 0.2013 0.4328 0.1313 0.092 Uiso 1 1 calc GR . . . .
H14B H 0.1607 0.4457 0.0294 0.092 Uiso 1 1 calc GR . . . .
H14C H 0.3026 0.4423 0.0597 0.092 Uiso 1 1 calc GR . . . .
C15 C 0.3394(10) 0.2540(5) -0.3676(6) 0.062(3) Uani 1 1 d . . . . .
H15A H 0.2955 0.3024 -0.3625 0.093 Uiso 1 1 calc GR . . . .
H15B H 0.3090 0.2270 -0.4210 0.093 Uiso 1 1 calc GR . . . .
H15C H 0.4269 0.2642 -0.3712 0.093 Uiso 1 1 calc GR . . . .
C16 C 0.3396(10) 0.0795(5) -0.3799(6) 0.065(3) Uani 1 1 d . . . . .
H16A H 0.2722 0.0907 -0.4231 0.098 Uiso 1 1 calc GR . . . .
H16B H 0.3427 0.0244 -0.3684 0.098 Uiso 1 1 calc GR . . . .
H16C H 0.4168 0.0960 -0.4035 0.098 Uiso 1 1 calc GR . . . .
C17 C 0.0161(7) -0.0903(4) 0.1962(4) 0.0264(18) Uani 1 1 d . . . . .
C18 C 0.4914(7) 0.3652(4) 0.2281(5) 0.0310(19) Uani 1 1 d . . . . .
H18 H 0.4984 0.3885 0.1720 0.037 Uiso 1 1 calc R . . . .
C19 C 0.4882(8) 0.2820(4) 0.2363(5) 0.0316(19) Uani 1 1 d . . . . .
C20 C 0.5005(8) 0.2343(4) 0.1611(5) 0.034(2) Uani 1 1 d . . . . .
H20 H 0.5133 0.2565 0.1051 0.041 Uiso 1 1 calc R . . . .
C21 C 0.4936(8) 0.1554(5) 0.1693(5) 0.036(2) Uani 1 1 d . . . . .
C22 C 0.4717(8) 0.1200(4) 0.2520(5) 0.041(2) Uani 1 1 d . . . . .
H22 H 0.4653 0.0660 0.2565 0.050 Uiso 1 1 calc R . . . .
C23 C 0.4596(9) 0.1671(4) 0.3274(5) 0.044(2) Uani 1 1 d . . . . .
H23 H 0.4443 0.1439 0.3824 0.053 Uiso 1 1 calc R . . . .
C24 C 0.4700(8) 0.2495(4) 0.3228(5) 0.034(2) Uani 1 1 d . . . . .
C25 C 0.4641(7) 0.2973(4) 0.3985(5) 0.0275(18) Uani 1 1 d . . . . .
H25 H 0.4510 0.2751 0.4544 0.033 Uiso 1 1 calc R . . . .
C26 C 0.4774(7) 0.3760(4) 0.3918(5) 0.0273(18) Uani 1 1 d . . . . .
La1 La 0.19554(4) 0.01380(2) -0.00228(3) 0.02727(16) Uani 1 1 d . . . . .
N1 N 0.2162(6) 0.1711(3) 0.0253(4) 0.0315(16) Uani 1 1 d . . . . .
N2 N 0.2712(6) 0.1092(3) -0.1367(4) 0.0335(16) Uani 1 1 d . . . . .
O1 O 0.1292(5) 0.0365(3) 0.1582(3) 0.0351(13) Uani 1 1 d . . . . .
O2 O -0.0968(5) 0.0385(3) 0.1518(3) 0.0341(14) Uani 1 1 d . . . . .
O3 O 0.0188(5) 0.0341(3) 0.2965(3) 0.0401(15) Uani 1 1 d . . . . .
O4 O 0.4820(5) 0.4243(3) 0.4636(3) 0.0279(12) Uani 1 1 d . . . . .
O5 O 0.4086(5) 0.0397(3) 0.0741(4) 0.0437(15) Uani 1 1 d . . . . .
O6 O 0.6344(5) 0.0569(3) 0.0912(3) 0.0360(14) Uani 1 1 d . . . . .
O7 O 0.5106(5) 0.1456(3) -0.0050(3) 0.0423(15) Uani 1 1 d . . . . .
O8 O 0.2830(6) -0.1069(3) 0.0834(4) 0.0595(19) Uani 1 1 d . . . . .
H8A H 0.2219 -0.1360 0.1009 0.089 Uiso 1 1 d GR . . . .
H8B H 0.3286 -0.0928 0.1311 0.089 Uiso 1 1 d GR . . . .
S1 S 0.01670(19) 0.01291(11) 0.20270(12) 0.0292(5) Uani 1 1 d . . . . .
S2 S 0.5131(2) 0.09520(11) 0.07393(13) 0.0351(5) Uani 1 1 d . . . . .
O0AA O 0.6177(16) 0.3313(12) -0.0718(10) 0.282(9) Uani 1 1 d . . . . .
O1AA O 0.523(5) 0.460(3) -0.003(3) 0.34(2) Uiso 0.5 1 d . . P . .


_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
C1 H1 0.9300 . ?
C1 C2 1.396(10) . ?
C1 N1 1.337(9) . ?
C2 C3 1.364(11) . ?
C2 C13 1.523(10) . ?
C3 C4 1.433(11) . ?
C3 C14 1.519(10) . ?
C4 C5 1.431(11) . ?
C4 C12 1.425(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.322(11) . ?
C6 H6 0.9300 . ?
C6 C7 1.420(11) . ?
C7 C8 1.404(11) . ?
C7 C11 1.404(10) . ?
C8 C9 1.392(11) . ?
C8 C15 1.523(10) . ?
C9 C10 1.394(10) . ?
C9 C16 1.519(11) . ?
C10 H10 0.9300 . ?
C10 N2 1.320(9) . ?
C11 C12 1.420(10) . ?
C11 N2 1.362(9) . ?
C12 N1 1.379(9) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.364(9) 2_545 ?
C17 C26 1.433(9) 2_545 ?
C17 S1 1.771(7) . ?
C18 C17 1.364(9) 2 ?
C18 H18 0.9300 . ?
C18 C19 1.432(10) . ?
C19 C20 1.396(10) . ?
C19 C24 1.421(10) . ?
C20 H20 0.9300 . ?
C20 C21 1.360(10) . ?
C21 C22 1.401(10) . ?
C21 S2 1.772(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.391(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.418(10) . ?
C24 C25 1.396(9) . ?
C25 H25 0.9300 . ?
C25 C26 1.360(9) . ?
C26 C17 1.433(9) 2 ?
C26 O4 1.349(8) . ?
La1 La1 4.2317(10) 3 ?
La1 N1 2.735(6) . ?
La1 N2 2.736(6) . ?
La1 O1 2.551(5) . ?
La1 O2 2.570(5) 3 ?
La1 O4 2.554(5) 4_565 ?
La1 O4 2.537(5) 2_545 ?
La1 O5 2.540(6) . ?
La1 O6 2.607(5) 3_655 ?
La1 O8 2.581(5) . ?
O1 S1 1.464(5) . ?
O2 La1 2.570(5) 3 ?
O2 S1 1.467(6) . ?
O3 S1 1.437(5) . ?
O4 La1 2.537(5) 2 ?
O4 La1 2.554(5) 4_666 ?
O5 S2 1.471(6) . ?
O6 La1 2.607(5) 3_655 ?
O6 S2 1.470(5) . ?
O7 S2 1.456(5) . ?
O8 H8A 0.8744 . ?
O8 H8B 0.8739 . ?
O1AA O1AA 1.48(8) 3_665 ?

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
C2 C1 H1 117.1 . . ?
N1 C1 H1 117.1 . . ?
N1 C1 C2 125.8(7) . . ?
C1 C2 C13 117.0(7) . . ?
C3 C2 C1 118.4(7) . . ?
C3 C2 C13 124.6(7) . . ?
C2 C3 C4 118.8(7) . . ?
C2 C3 C14 121.0(8) . . ?
C4 C3 C14 120.2(7) . . ?
C5 C4 C3 123.2(7) . . ?
C12 C4 C3 119.0(7) . . ?
C12 C4 C5 117.8(7) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.1(8) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 118.4 . . ?
C5 C6 C7 123.2(8) . . ?
C7 C6 H6 118.4 . . ?
C8 C7 C6 123.8(7) . . ?
C11 C7 C6 117.6(7) . . ?
C11 C7 C8 118.6(7) . . ?
C7 C8 C15 121.2(8) . . ?
C9 C8 C7 118.9(7) . . ?
C9 C8 C15 119.9(7) . . ?
C8 C9 C10 117.6(7) . . ?
C8 C9 C16 123.8(7) . . ?
C10 C9 C16 118.5(7) . . ?
C9 C10 H10 117.5 . . ?
N2 C10 C9 125.1(7) . . ?
N2 C10 H10 117.5 . . ?
C7 C11 C12 120.4(7) . . ?
N2 C11 C7 122.1(7) . . ?
N2 C11 C12 117.5(6) . . ?
C11 C12 C4 119.9(6) . . ?
N1 C12 C4 121.0(7) . . ?
N1 C12 C11 119.2(6) . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C26 122.1(6) 2_545 2_545 ?
C18 C17 S1 121.0(5) 2_545 . ?
C26 C17 S1 116.9(5) 2_545 . ?
C17 C18 H18 120.5 2 . ?
C17 C18 C19 119.0(6) 2 . ?
C19 C18 H18 120.5 . . ?
C20 C19 C18 120.8(7) . . ?
C20 C19 C24 121.0(7) . . ?
C24 C19 C18 118.2(6) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(7) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 121.4(7) . . ?
C20 C21 S2 119.9(6) . . ?
C22 C21 S2 118.7(6) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 C21 118.7(7) . . ?
C23 C22 H22 120.6 . . ?
C22 C23 H23 119.1 . . ?
C22 C23 C24 121.9(7) . . ?
C24 C23 H23 119.1 . . ?
C23 C24 C19 116.7(6) . . ?
C25 C24 C19 120.7(6) . . ?
C25 C24 C23 122.6(7) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 120.9(7) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C17 118.5(6) . 2 ?
O4 C26 C17 118.1(6) . 2 ?
O4 C26 C25 123.4(6) . . ?
N1 La1 La1 100.40(14) . 3 ?
N1 La1 N2 59.64(17) . . ?
N2 La1 La1 114.29(14) . 3 ?
O1 La1 La1 71.11(12) . 3 ?
O1 La1 N1 74.58(16) . . ?
O1 La1 N2 134.21(16) . . ?
O1 La1 O2 137.44(16) . 3 ?
O1 La1 O4 80.21(16) . 4_565 ?
O1 La1 O6 141.30(16) . 3_655 ?
O1 La1 O8 76.98(18) . . ?
O2 La1 La1 67.03(12) 3 3 ?
O2 La1 N1 119.97(17) 3 . ?
O2 La1 N2 72.77(17) 3 . ?
O2 La1 O6 70.70(16) 3 3_655 ?
O2 La1 O8 105.61(19) 3 . ?
O4 La1 La1 33.65(10) 4_565 3 ?
O4 La1 La1 33.90(10) 2_545 3 ?
O4 La1 N1 128.20(16) 2_545 . ?
O4 La1 N1 71.62(17) 4_565 . ?
O4 La1 N2 84.53(17) 4_565 . ?
O4 La1 N2 141.45(18) 2_545 . ?
O4 La1 O1 68.36(16) 2_545 . ?
O4 La1 O2 72.75(15) 2_545 3 ?
O4 La1 O2 69.39(16) 4_565 3 ?
O4 La1 O4 67.55(16) 2_545 4_565 ?
O4 La1 O5 132.50(17) 2_545 . ?
O4 La1 O6 112.86(15) 2_545 3_655 ?
O4 La1 O6 137.62(16) 4_565 3_655 ?
O4 La1 O8 136.99(17) 4_565 . ?
O4 La1 O8 70.26(18) 2_545 . ?
O5 La1 La1 152.23(12) . 3 ?
O5 La1 N1 72.35(18) . . ?
O5 La1 N2 85.73(19) . . ?
O5 La1 O1 81.14(17) . . ?
O5 La1 O2 140.15(16) . 3 ?
O5 La1 O4 142.65(16) . 4_565 ?
O5 La1 O6 70.60(16) . 3_655 ?
O5 La1 O8 67.9(2) . . ?
O6 La1 La1 132.74(12) 3_655 3 ?
O6 La1 N1 118.72(17) 3_655 . ?
O6 La1 N2 70.51(17) 3_655 . ?
O8 La1 La1 103.81(15) . 3 ?
O8 La1 N1 133.8(2) . . ?
O8 La1 N2 136.43(19) . . ?
O8 La1 O6 68.27(17) . 3_655 ?
C1 N1 C12 117.0(6) . . ?
C1 N1 La1 122.0(5) . . ?
C12 N1 La1 121.0(4) . . ?
C10 N2 C11 117.5(6) . . ?
C10 N2 La1 119.8(5) . . ?
C11 N2 La1 122.4(5) . . ?
S1 O1 La1 131.0(3) . . ?
S1 O2 La1 129.4(3) . 3 ?
C26 O4 La1 123.6(4) . 2 ?
C26 O4 La1 114.0(4) . 4_666 ?
La1 O4 La1 112.45(16) 2 4_666 ?
S2 O5 La1 141.4(4) . . ?
S2 O6 La1 139.3(3) . 3_655 ?
La1 O8 H8A 110.1 . . ?
La1 O8 H8B 110.5 . . ?
H8A O8 H8B 108.4 . . ?
O1 S1 C17 104.6(3) . . ?
O1 S1 O2 111.7(3) . . ?
O2 S1 C17 105.7(3) . . ?
O3 S1 C17 107.8(3) . . ?
O3 S1 O1 113.3(3) . . ?
O3 S1 O2 113.2(3) . . ?
O5 S2 C21 104.7(4) . . ?
O6 S2 C21 105.2(3) . . ?
O6 S2 O5 112.3(3) . . ?
O7 S2 C21 107.4(3) . . ?
O7 S2 O5 113.8(4) . . ?
O7 S2 O6 112.6(3) . . ?

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
C1 C2 C3 C4 -0.7(13) . . . . ?
C1 C2 C3 C14 179.2(9) . . . . ?
C2 C1 N1 C12 1.4(12) . . . . ?
C2 C1 N1 La1 -175.7(6) . . . . ?
C2 C3 C4 C5 -179.7(9) . . . . ?
C2 C3 C4 C12 1.4(13) . . . . ?
C3 C4 C5 C6 -176.6(10) . . . . ?
C3 C4 C12 C11 178.3(8) . . . . ?
C3 C4 C12 N1 -0.8(12) . . . . ?
C4 C5 C6 C7 -1.7(16) . . . . ?
C4 C12 N1 C1 -0.6(11) . . . . ?
C4 C12 N1 La1 176.5(6) . . . . ?
C5 C4 C12 C11 -0.7(12) . . . . ?
C5 C4 C12 N1 -179.7(8) . . . . ?
C5 C6 C7 C8 176.8(10) . . . . ?
C5 C6 C7 C11 -0.6(15) . . . . ?
C6 C7 C8 C9 176.6(9) . . . . ?
C6 C7 C8 C15 -1.7(14) . . . . ?
C6 C7 C11 C12 2.2(13) . . . . ?
C6 C7 C11 N2 -178.3(8) . . . . ?
C7 C8 C9 C10 4.2(12) . . . . ?
C7 C8 C9 C16 -178.4(9) . . . . ?
C7 C11 C12 C4 -1.5(12) . . . . ?
C7 C11 C12 N1 177.5(8) . . . . ?
C7 C11 N2 C10 -0.4(12) . . . . ?
C7 C11 N2 La1 -173.9(6) . . . . ?
C8 C7 C11 C12 -175.3(8) . . . . ?
C8 C7 C11 N2 4.2(13) . . . . ?
C8 C9 C10 N2 -0.4(13) . . . . ?
C9 C10 N2 C11 -1.6(13) . . . . ?
C9 C10 N2 La1 172.1(7) . . . . ?
C11 C7 C8 C9 -6.0(13) . . . . ?
C11 C7 C8 C15 175.6(8) . . . . ?
C11 C12 N1 C1 -179.6(7) . . . . ?
C11 C12 N1 La1 -2.5(10) . . . . ?
C12 C4 C5 C6 2.3(14) . . . . ?
C12 C11 N2 C10 179.1(8) . . . . ?
C12 C11 N2 La1 5.7(10) . . . . ?
C13 C2 C3 C4 178.9(8) . . . . ?
C13 C2 C3 C14 -1.2(15) . . . . ?
C14 C3 C4 C5 0.4(14) . . . . ?
C14 C3 C4 C12 -178.5(9) . . . . ?
C15 C8 C9 C10 -177.4(8) . . . . ?
C15 C8 C9 C16 0.0(14) . . . . ?
C16 C9 C10 N2 -177.9(8) . . . . ?
C17 C18 C19 C20 -177.5(8) 2 . . . ?
C17 C18 C19 C24 3.7(12) 2 . . . ?
C17 C26 O4 La1 -70.8(7) 2 . . 4_666 ?
C17 C26 O4 La1 72.1(8) 2 . . 2 ?
C18 C17 S1 O1 125.5(7) 2_545 . . . ?
C18 C17 S1 O2 -116.5(7) 2_545 . . . ?
C18 C17 S1 O3 4.7(8) 2_545 . . . ?
C18 C19 C20 C21 -178.0(8) . . . . ?
C18 C19 C24 C23 176.2(8) . . . . ?
C18 C19 C24 C25 -4.5(12) . . . . ?
C19 C20 C21 C22 1.4(13) . . . . ?
C19 C20 C21 S2 -178.4(6) . . . . ?
C19 C24 C25 C26 -0.9(13) . . . . ?
C20 C19 C24 C23 -2.6(13) . . . . ?
C20 C19 C24 C25 176.7(8) . . . . ?
C20 C21 C22 C23 -1.4(14) . . . . ?
C20 C21 S2 O5 -132.1(7) . . . . ?
C20 C21 S2 O6 109.4(7) . . . . ?
C20 C21 S2 O7 -10.8(8) . . . . ?
C21 C22 C23 C24 -0.6(14) . . . . ?
C22 C21 S2 O5 48.1(8) . . . . ?
C22 C21 S2 O6 -70.4(8) . . . . ?
C22 C21 S2 O7 169.4(7) . . . . ?
C22 C23 C24 C19 2.5(13) . . . . ?
C22 C23 C24 C25 -176.8(9) . . . . ?
C23 C24 C25 C26 178.4(8) . . . . ?
C24 C19 C20 C21 0.7(13) . . . . ?
C24 C25 C26 C17 6.8(12) . . . 2 ?
C24 C25 C26 O4 -174.8(7) . . . . ?
C25 C26 O4 La1 -106.3(7) . . . 2 ?
C25 C26 O4 La1 110.7(7) . . . 4_666 ?
C26 C17 S1 O1 -55.1(7) 2_545 . . . ?
C26 C17 S1 O2 62.9(7) 2_545 . . . ?
C26 C17 S1 O3 -175.9(6) 2_545 . . . ?
La1 O1 S1 C17 59.7(4) . . . . ?
La1 O1 S1 O2 -54.1(5) . . . . ?
La1 O1 S1 O3 176.8(3) . . . . ?
La1 O2 S1 C17 -40.5(4) 3 . . . ?
La1 O2 S1 O1 72.7(4) 3 . . . ?
La1 O2 S1 O3 -158.1(3) 3 . . . ?
La1 O5 S2 C21 101.3(5) . . . . ?
La1 O5 S2 O6 -145.1(4) . . . . ?
La1 O5 S2 O7 -15.6(6) . . . . ?
La1 O6 S2 C21 -159.9(4) 3_655 . . . ?
La1 O6 S2 O5 86.9(5) 3_655 . . . ?
La1 O6 S2 O7 -43.2(6) 3_655 . . . ?
N1 C1 C2 C3 -0.7(13) . . . . ?
N1 C1 C2 C13 179.6(8) . . . . ?
N2 C11 C12 C4 178.9(8) . . . . ?
N2 C11 C12 N1 -2.1(11) . . . . ?
S2 C21 C22 C23 178.4(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method Hydrothermal
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_Compound6
_database_code_depnum_ccdc_archive 'CCDC 1426615'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;
_audit_creation_date             2015-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 N2 O8 Pr S2, 3(H2 O)'
_chemical_formula_sum            'C22 H21 N2 O11 Pr S2'
_chemical_formula_weight         694.44
_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'
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'
Pr Pr -0.2180 2.8214 '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'

_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      triclinic
_space_group_IT_number           2
_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                   9.2708(2)
_cell_length_b                   11.9699(3)
_cell_length_c                   12.7725(3)
_cell_angle_alpha                106.5890(10)
_cell_angle_beta                 110.161(2)
_cell_angle_gamma                99.3770(10)
_cell_volume                     1220.16(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.234
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light green'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.890
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             692
_exptl_crystal_recrystallization_method Hydrothermal
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1357
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37191
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.989
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enraf Nonius FR590'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3981
_reflns_number_total             4978
_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_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_refine_diff_density_max         1.619
_refine_diff_density_min         -1.133
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4978
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      0.967
_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)+(0.0539P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0959
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O8-H8A = O8-H8B
 0.84 with sigma of 0.02
3.a Free rotating group:
 O9(H9A,H9B), O10(H10A,H10B), O11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C1 C 0.6927(5) 0.3420(4) 0.6423(4) 0.0319(9) Uani 1 1 d . . . . .
C2 C 0.7510(5) 0.2731(4) 0.7079(4) 0.0322(9) Uani 1 1 d . . . . .
H2 H 0.8586 0.2980 0.7611 0.039 Uiso 1 1 calc R . . . .
C3 C 0.6476(5) 0.1654(4) 0.6940(4) 0.0340(9) Uani 1 1 d . . . . .
C4 C 0.6981(5) 0.0918(4) 0.7617(4) 0.0361(10) Uani 1 1 d . . . . .
H4 H 0.8046 0.1142 0.8162 0.043 Uiso 1 1 calc R . . . .
C5 C 0.5940(5) -0.0098(4) 0.7482(4) 0.0355(9) Uani 1 1 d . . . . .
C6 C 0.4329(5) -0.0480(4) 0.6636(4) 0.0405(10) Uani 1 1 d . . . . .
H6 H 0.3623 -0.1184 0.6545 0.049 Uiso 1 1 calc R . . . .
C7 C 0.3809(5) 0.0183(4) 0.5953(4) 0.0392(10) Uani 1 1 d . . . . .
H7 H 0.2748 -0.0082 0.5391 0.047 Uiso 1 1 calc R . . . .
C8 C 0.4851(5) 0.1274(4) 0.6081(4) 0.0336(9) Uani 1 1 d . . . . .
C9 C 0.4295(5) 0.1994(4) 0.5434(4) 0.0334(9) Uani 1 1 d . . . . .
H9 H 0.3234 0.1733 0.4872 0.040 Uiso 1 1 calc R . . . .
C10 C 0.5283(5) 0.3076(4) 0.5615(3) 0.0303(9) Uani 1 1 d . . . . .
C11 C 0.8870(5) 0.6744(4) 0.4389(4) 0.0456(11) Uani 1 1 d . . . . .
H11 H 0.9265 0.6440 0.4990 0.055 Uiso 1 1 calc R . . . .
C12 C 0.9837(6) 0.7802(5) 0.4445(5) 0.0547(13) Uani 1 1 d . . . . .
H12 H 1.0853 0.8181 0.5069 0.066 Uiso 1 1 calc R . . . .
C13 C 0.9299(6) 0.8270(5) 0.3599(5) 0.0550(13) Uani 1 1 d . . . . .
H13 H 0.9936 0.8980 0.3638 0.066 Uiso 1 1 calc R . . . .
C14 C 0.7746(6) 0.7677(4) 0.2637(4) 0.0456(11) Uani 1 1 d . . . . .
C15 C 0.7083(7) 0.8139(5) 0.1728(5) 0.0567(13) Uani 1 1 d . . . . .
H15 H 0.7697 0.8831 0.1721 0.068 Uiso 1 1 calc R . . . .
C16 C 0.5585(7) 0.7589(5) 0.0883(5) 0.0589(14) Uani 1 1 d . . . . .
H16 H 0.5154 0.7925 0.0316 0.071 Uiso 1 1 calc R . . . .
C17 C 0.4635(6) 0.6490(5) 0.0838(4) 0.0469(12) Uani 1 1 d . . . . .
C18 C 0.3070(6) 0.5874(5) -0.0041(4) 0.0564(13) Uani 1 1 d . . . . .
H18 H 0.2582 0.6196 -0.0606 0.068 Uiso 1 1 calc R . . . .
C19 C 0.2267(6) 0.4804(5) -0.0063(5) 0.0581(14) Uani 1 1 d . . . . .
H19 H 0.1237 0.4387 -0.0656 0.070 Uiso 1 1 calc R . . . .
C20 C 0.2978(6) 0.4327(5) 0.0798(4) 0.0480(12) Uani 1 1 d . . . . .
H20 H 0.2426 0.3583 0.0757 0.058 Uiso 1 1 calc R . . . .
C21 C 0.5270(5) 0.5979(4) 0.1689(4) 0.0367(10) Uani 1 1 d . . . . .
C22 C 0.6863(5) 0.6615(4) 0.2650(4) 0.0364(10) Uani 1 1 d . . . . .
Pr1 Pr 0.54705(3) 0.43137(2) 0.35780(2) 0.03247(10) Uani 1 1 d . . . . .
N1 N 0.7414(4) 0.6150(3) 0.3521(3) 0.0361(8) Uani 1 1 d . . . . .
N2 N 0.4452(4) 0.4928(3) 0.1686(3) 0.0397(9) Uani 1 1 d . . . . .
O1 O 0.9804(3) 0.4979(3) 0.7362(3) 0.0403(7) Uani 1 1 d . . . . .
O2 O 0.7499(3) 0.5767(2) 0.7041(2) 0.0364(7) Uani 1 1 d . . . . .
O3 O 0.7975(3) 0.4652(3) 0.5346(2) 0.0382(7) Uani 1 1 d . . . . .
O4 O 0.4108(4) 0.0634(3) 0.0713(3) 0.0562(9) Uani 1 1 d . . . . .
O5 O 0.4180(4) 0.2223(3) 0.2402(3) 0.0476(8) Uani 1 1 d . . . . .
O6 O 0.1729(4) 0.0590(3) 0.1088(3) 0.0563(9) Uani 1 1 d . . . . .
O7 O 0.4755(3) 0.3860(2) 0.5096(2) 0.0316(6) Uani 1 1 d . . . . .
O8 O 0.7371(4) 0.3605(3) 0.2775(3) 0.0507(8) Uani 1 1 d D . . . .
H8A H 0.811(5) 0.416(4) 0.285(5) 0.076 Uiso 1 1 d DR . . . .
H8B H 0.734(7) 0.295(3) 0.235(5) 0.076 Uiso 1 1 d DR . . . .
O9 O 0.7606(5) 0.1484(4) 0.1601(4) 0.0840(13) Uani 1 1 d . . . . .
H9A H 0.8110 0.1489 0.1157 0.126 Uiso 1 1 d G . . . .
H9B H 0.6822 0.0838 0.1268 0.126 Uiso 1 1 d G . . . .
S1 S 0.81672(12) 0.48022(9) 0.65724(9) 0.0325(2) Uani 1 1 d . . . . .
S2 S 0.34559(13) 0.09305(9) 0.15888(9) 0.0364(3) Uani 1 1 d . . . . .
O10 O 0.9777(6) 0.2209(4) 0.0687(4) 0.0869(13) Uani 1 1 d . . . . .
H10A H 0.9763 0.1475 0.0600 0.130 Uiso 1 1 d G . . . .
H10B H 1.0548 0.2687 0.1345 0.130 Uiso 1 1 d G . . . .
O11 O 1.0368(9) 0.0802(6) 0.2961(5) 0.1210(19) Uani 1 1 d . . . . .
H11A H 1.0701 0.1497 0.2939 0.182 Uiso 1 1 d G . . . .
H11B H 0.9942 0.0267 0.2254 0.182 Uiso 1 1 d G . . . .


_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
C1 C2 1.379(5) . ?
C1 C10 1.424(6) . ?
C1 S1 1.773(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.401(6) . ?
C3 C4 1.426(6) . ?
C3 C8 1.426(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.351(6) . ?
C5 C6 1.411(6) . ?
C5 S2 1.765(4) 2_656 ?
C6 H6 0.9300 . ?
C6 C7 1.362(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.422(6) . ?
C8 C9 1.396(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.366(5) . ?
C10 O7 1.356(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(6) . ?
C11 N1 1.328(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.341(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.427(7) . ?
C14 C15 1.420(7) . ?
C14 C22 1.403(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.338(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.433(7) . ?
C17 C18 1.402(7) . ?
C17 C21 1.400(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.359(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(7) . ?
C20 H20 0.9300 . ?
C20 N2 1.348(6) . ?
C21 C22 1.455(6) . ?
C21 N2 1.357(6) . ?
C22 N1 1.365(5) . ?
Pr1 Pr1 3.9873(4) 2_666 ?
Pr1 N1 2.641(3) . ?
Pr1 N2 2.634(4) . ?
Pr1 O2 2.566(3) 2_666 ?
Pr1 O3 2.493(3) . ?
Pr1 O5 2.364(3) . ?
Pr1 O7 2.444(3) 2_666 ?
Pr1 O7 2.422(3) . ?
Pr1 O8 2.473(3) . ?
O1 S1 1.443(3) . ?
O2 Pr1 2.566(3) 2_666 ?
O2 S1 1.473(3) . ?
O3 S1 1.467(3) . ?
O4 S2 1.432(3) . ?
O5 S2 1.478(3) . ?
O6 S2 1.439(3) . ?
O7 Pr1 2.444(3) 2_666 ?
O8 H8A 0.83(2) . ?
O8 H8B 0.81(2) . ?
O9 H9A 0.8507 . ?
O9 H9B 0.8508 . ?
S2 C5 1.765(4) 2_656 ?
O10 H10A 0.8515 . ?
O10 H10B 0.8509 . ?
O11 H11A 0.8511 . ?
O11 H11B 0.8508 . ?

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
C2 C1 C10 121.6(4) . . ?
C2 C1 S1 121.9(3) . . ?
C10 C1 S1 116.5(3) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.7(4) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 122.8(4) . . ?
C2 C3 C8 118.6(4) . . ?
C8 C3 C4 118.6(4) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 S2 120.6(3) . 2_656 ?
C6 C5 S2 118.8(3) . 2_656 ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(4) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.5(4) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C3 118.1(4) . . ?
C9 C8 C3 120.3(4) . . ?
C9 C8 C7 121.5(4) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C1 118.6(4) . . ?
O7 C10 C1 118.4(3) . . ?
O7 C10 C9 123.0(3) . . ?
C12 C11 H11 118.4 . . ?
N1 C11 H11 118.4 . . ?
N1 C11 C12 123.3(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 122.8(4) . . ?
C22 C14 C13 116.3(4) . . ?
C22 C14 C15 120.9(5) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.7(5) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.0(5) . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 123.0(5) . . ?
C21 C17 C16 120.0(4) . . ?
C21 C17 C18 117.0(5) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(5) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.5(5) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.5 . . ?
N2 C20 C19 121.0(5) . . ?
N2 C20 H20 119.5 . . ?
C17 C21 C22 119.0(4) . . ?
N2 C21 C17 123.2(4) . . ?
N2 C21 C22 117.8(4) . . ?
C14 C22 C21 118.3(4) . . ?
N1 C22 C14 123.5(4) . . ?
N1 C22 C21 118.2(4) . . ?
N1 Pr1 Pr1 106.08(8) . 2_666 ?
N2 Pr1 Pr1 121.96(8) . 2_666 ?
N2 Pr1 N1 62.41(11) . . ?
O2 Pr1 Pr1 68.34(6) 2_666 2_666 ?
O2 Pr1 N1 118.05(9) 2_666 . ?
O2 Pr1 N2 70.08(10) 2_666 . ?
O3 Pr1 Pr1 75.00(7) . 2_666 ?
O3 Pr1 N1 79.45(10) . . ?
O3 Pr1 N2 140.88(10) . . ?
O3 Pr1 O2 142.43(9) . 2_666 ?
O5 Pr1 Pr1 116.56(8) . 2_666 ?
O5 Pr1 N1 137.33(11) . . ?
O5 Pr1 N2 92.03(11) . . ?
O5 Pr1 O2 78.36(10) . 2_666 ?
O5 Pr1 O3 112.30(10) . . ?
O5 Pr1 O7 85.26(10) . . ?
O5 Pr1 O7 144.23(11) . 2_666 ?
O5 Pr1 O8 75.11(11) . . ?
O7 Pr1 Pr1 34.79(6) 2_666 2_666 ?
O7 Pr1 Pr1 35.15(6) . 2_666 ?
O7 Pr1 N1 135.76(10) . . ?
O7 Pr1 N1 75.04(10) 2_666 . ?
O7 Pr1 N2 144.06(10) . . ?
O7 Pr1 N2 93.51(10) 2_666 . ?
O7 Pr1 O2 70.50(9) 2_666 2_666 ?
O7 Pr1 O2 74.29(9) . 2_666 ?
O7 Pr1 O3 84.23(9) 2_666 . ?
O7 Pr1 O3 71.06(9) . . ?
O7 Pr1 O7 69.93(10) . 2_666 ?
O7 Pr1 O8 140.60(10) 2_666 . ?
O7 Pr1 O8 128.57(11) . . ?
O8 Pr1 Pr1 148.47(9) . 2_666 ?
O8 Pr1 N1 69.29(11) . . ?
O8 Pr1 N2 84.61(12) . . ?
O8 Pr1 O2 142.38(10) . 2_666 ?
O8 Pr1 O3 73.49(11) . . ?
C11 N1 C22 117.2(4) . . ?
C11 N1 Pr1 122.6(3) . . ?
C22 N1 Pr1 119.8(3) . . ?
C20 N2 C21 118.4(4) . . ?
C20 N2 Pr1 120.3(3) . . ?
C21 N2 Pr1 120.3(3) . . ?
S1 O2 Pr1 127.57(15) . 2_666 ?
S1 O3 Pr1 128.06(16) . . ?
S2 O5 Pr1 174.3(2) . . ?
C10 O7 Pr1 115.7(2) . 2_666 ?
C10 O7 Pr1 124.5(2) . . ?
Pr1 O7 Pr1 110.07(10) . 2_666 ?
Pr1 O8 H8A 114(4) . . ?
Pr1 O8 H8B 133(4) . . ?
H8A O8 H8B 112(6) . . ?
H9A O9 H9B 109.4 . . ?
O1 S1 C1 109.40(18) . . ?
O1 S1 O2 112.77(18) . . ?
O1 S1 O3 112.50(18) . . ?
O2 S1 C1 106.05(18) . . ?
O3 S1 C1 104.75(18) . . ?
O3 S1 O2 110.85(17) . . ?
O4 S2 C5 106.9(2) . 2_656 ?
O4 S2 O5 111.5(2) . . ?
O4 S2 O6 114.1(2) . . ?
O5 S2 C5 104.83(19) . 2_656 ?
O6 S2 C5 106.9(2) . 2_656 ?
O6 S2 O5 112.0(2) . . ?
H10A O10 H10B 109.5 . . ?
H11A O11 H11B 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
C1 C2 C3 C4 -177.8(4) . . . . ?
C1 C2 C3 C8 2.6(6) . . . . ?
C1 C10 O7 Pr1 -71.8(4) . . . 2_666 ?
C1 C10 O7 Pr1 70.5(4) . . . . ?
C2 C1 C10 C9 -4.3(6) . . . . ?
C2 C1 C10 O7 173.1(4) . . . . ?
C2 C1 S1 O1 5.2(4) . . . . ?
C2 C1 S1 O2 -116.6(3) . . . . ?
C2 C1 S1 O3 126.1(3) . . . . ?
C2 C3 C4 C5 178.3(4) . . . . ?
C2 C3 C8 C7 -179.6(4) . . . . ?
C2 C3 C8 C9 -2.9(6) . . . . ?
C3 C4 C5 C6 1.9(7) . . . . ?
C3 C4 C5 S2 -174.9(3) . . . 2_656 ?
C3 C8 C9 C10 -0.5(6) . . . . ?
C4 C3 C8 C7 0.8(6) . . . . ?
C4 C3 C8 C9 177.5(4) . . . . ?
C4 C5 C6 C7 -0.5(7) . . . . ?
C5 C6 C7 C8 -0.9(7) . . . . ?
C6 C7 C8 C3 0.7(6) . . . . ?
C6 C7 C8 C9 -176.0(4) . . . . ?
C7 C8 C9 C10 176.1(4) . . . . ?
C8 C3 C4 C5 -2.1(6) . . . . ?
C8 C9 C10 C1 4.0(6) . . . . ?
C8 C9 C10 O7 -173.3(4) . . . . ?
C9 C10 O7 Pr1 105.5(4) . . . 2_666 ?
C9 C10 O7 Pr1 -112.2(4) . . . . ?
C10 C1 C2 C3 1.0(6) . . . . ?
C10 C1 S1 O1 -176.5(3) . . . . ?
C10 C1 S1 O2 61.6(3) . . . . ?
C10 C1 S1 O3 -55.7(3) . . . . ?
C11 C12 C13 C14 -0.7(8) . . . . ?
C12 C11 N1 C22 0.0(7) . . . . ?
C12 C11 N1 Pr1 -172.2(4) . . . . ?
C12 C13 C14 C15 178.3(5) . . . . ?
C12 C13 C14 C22 0.4(7) . . . . ?
C13 C14 C15 C16 -176.1(5) . . . . ?
C13 C14 C22 C21 179.9(4) . . . . ?
C13 C14 C22 N1 0.2(7) . . . . ?
C14 C15 C16 C17 -2.8(8) . . . . ?
C14 C22 N1 C11 -0.4(6) . . . . ?
C14 C22 N1 Pr1 172.1(3) . . . . ?
C15 C14 C22 C21 1.9(7) . . . . ?
C15 C14 C22 N1 -177.7(4) . . . . ?
C15 C16 C17 C18 -179.1(5) . . . . ?
C15 C16 C17 C21 0.2(8) . . . . ?
C16 C17 C18 C19 176.8(5) . . . . ?
C16 C17 C21 C22 3.4(7) . . . . ?
C16 C17 C21 N2 -178.7(4) . . . . ?
C17 C18 C19 C20 1.4(8) . . . . ?
C17 C21 C22 C14 -4.4(6) . . . . ?
C17 C21 C22 N1 175.2(4) . . . . ?
C17 C21 N2 C20 2.4(6) . . . . ?
C17 C21 N2 Pr1 -166.1(3) . . . . ?
C18 C17 C21 C22 -177.2(4) . . . . ?
C18 C17 C21 N2 0.7(7) . . . . ?
C18 C19 C20 N2 1.8(8) . . . . ?
C19 C20 N2 C21 -3.6(7) . . . . ?
C19 C20 N2 Pr1 164.8(4) . . . . ?
C21 C17 C18 C19 -2.5(7) . . . . ?
C21 C22 N1 C11 180.0(4) . . . . ?
C21 C22 N1 Pr1 -7.6(5) . . . . ?
C22 C14 C15 C16 1.7(8) . . . . ?
C22 C21 N2 C20 -179.7(4) . . . . ?
C22 C21 N2 Pr1 11.9(5) . . . . ?
Pr1 O2 S1 C1 -41.1(2) 2_666 . . . ?
Pr1 O2 S1 O1 -160.83(17) 2_666 . . . ?
Pr1 O2 S1 O3 72.0(2) 2_666 . . . ?
Pr1 O3 S1 C1 61.1(2) . . . . ?
Pr1 O3 S1 O1 179.85(18) . . . . ?
Pr1 O3 S1 O2 -52.8(2) . . . . ?
N1 C11 C12 C13 0.6(8) . . . . ?
N2 C21 C22 C14 177.6(4) . . . . ?
N2 C21 C22 N1 -2.8(6) . . . . ?
S1 C1 C2 C3 179.1(3) . . . . ?
S1 C1 C10 C9 177.4(3) . . . . ?
S1 C1 C10 O7 -5.2(5) . . . . ?
S2 C5 C6 C7 176.4(3) 2_656 . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_Compound7
_database_code_depnum_ccdc_archive 'CCDC 1426616'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;
_audit_creation_date             2015-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 N2 Nd O8 S2, 3(H2 O)'
_chemical_formula_sum            'C22 H21 N2 Nd O11 S2'
_chemical_formula_weight         697.77
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1943 3.0179 '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'

_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      triclinic
_space_group_IT_number           2
_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                   9.2648(3)
_cell_length_b                   11.9499(3)
_cell_length_c                   12.7485(5)
_cell_angle_alpha                106.629(2)
_cell_angle_beta                 110.177(2)
_cell_angle_gamma                99.313(2)
_cell_volume                     1214.98(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    20683
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.373
_cell_measurement_theta_min      2.910
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.890
_exptl_absorpt_coefficient_mu    2.375
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.907
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             694
_exptl_crystal_recrystallization_method Hydrothermal
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1337
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            38139
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.285
_diffrn_reflns_theta_min         2.995
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enraf Nonius FR590'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3465
_reflns_number_total             4915
_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       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_refine_diff_density_max         2.403
_refine_diff_density_min         -1.312
_refine_diff_density_rms         0.174
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4915
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.041
_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)+(0.0627P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1204
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O8-H8A = O8-H8B
 0.84 with sigma of 0.02
3.a Free rotating group:
 O9(H9A,H9B), O10(H10A,H10B), O11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C1 C 0.6920(8) 0.3415(5) 0.6428(6) 0.0248(14) Uani 1 1 d . . . . .
C2 C 0.7523(8) 0.2735(5) 0.7080(6) 0.0254(14) Uani 1 1 d . . . . .
H2 H 0.8601 0.2986 0.7609 0.031 Uiso 1 1 calc R . . . .
C3 C 0.6475(8) 0.1639(6) 0.6934(6) 0.0279(15) Uani 1 1 d . . . . .
C4 C 0.6977(8) 0.0919(5) 0.7620(6) 0.0296(15) Uani 1 1 d . . . . .
H4 H 0.8039 0.1151 0.8176 0.036 Uiso 1 1 calc R . . . .
C5 C 0.5930(8) -0.0108(5) 0.7476(6) 0.0267(14) Uani 1 1 d . . . . .
C6 C 0.4326(8) -0.0493(6) 0.6632(6) 0.0335(16) Uani 1 1 d . . . . .
H6 H 0.3622 -0.1201 0.6538 0.040 Uiso 1 1 calc R . . . .
C7 C 0.3801(8) 0.0179(6) 0.5946(6) 0.0351(16) Uani 1 1 d . . . . .
H7 H 0.2741 -0.0084 0.5381 0.042 Uiso 1 1 calc R . . . .
C8 C 0.4847(7) 0.1268(5) 0.6082(6) 0.0250(14) Uani 1 1 d . . . . .
C9 C 0.4292(8) 0.1999(5) 0.5430(6) 0.0269(14) Uani 1 1 d . . . . .
H9 H 0.3233 0.1738 0.4863 0.032 Uiso 1 1 calc R . . . .
C10 C 0.5277(7) 0.3081(5) 0.5614(5) 0.0238(14) Uani 1 1 d . . . . .
C11 C 0.8863(8) 0.6747(6) 0.4405(7) 0.0386(17) Uani 1 1 d . . . . .
H11 H 0.9247 0.6446 0.5012 0.046 Uiso 1 1 calc R . . . .
C12 C 0.9839(9) 0.7799(7) 0.4464(8) 0.049(2) Uani 1 1 d . . . . .
H12 H 1.0854 0.8182 0.5090 0.059 Uiso 1 1 calc R . . . .
C13 C 0.9285(9) 0.8262(7) 0.3589(7) 0.047(2) Uani 1 1 d . . . . .
H13 H 0.9923 0.8965 0.3617 0.057 Uiso 1 1 calc R . . . .
C14 C 0.7744(9) 0.7673(6) 0.2644(7) 0.0362(17) Uani 1 1 d . . . . .
C15 C 0.7083(10) 0.8136(7) 0.1732(7) 0.0460(19) Uani 1 1 d . . . . .
H15 H 0.7695 0.8828 0.1722 0.055 Uiso 1 1 calc R . . . .
C16 C 0.5577(12) 0.7576(7) 0.0883(8) 0.053(2) Uani 1 1 d . . . . .
H16 H 0.5142 0.7905 0.0309 0.064 Uiso 1 1 calc R . . . .
C17 C 0.4632(9) 0.6480(7) 0.0847(6) 0.0386(17) Uani 1 1 d . . . . .
C18 C 0.3074(10) 0.5867(8) -0.0031(7) 0.052(2) Uani 1 1 d . . . . .
H18 H 0.2596 0.6195 -0.0596 0.062 Uiso 1 1 calc R . . . .
C19 C 0.2242(9) 0.4786(8) -0.0070(7) 0.048(2) Uani 1 1 d . . . . .
H19 H 0.1205 0.4373 -0.0657 0.058 Uiso 1 1 calc R . . . .
C20 C 0.2991(8) 0.4318(8) 0.0799(6) 0.0406(18) Uani 1 1 d . . . . .
H20 H 0.2458 0.3562 0.0750 0.049 Uiso 1 1 calc R . . . .
C21 C 0.5274(8) 0.5974(6) 0.1701(6) 0.0299(15) Uani 1 1 d . . . . .
C22 C 0.6837(8) 0.6600(6) 0.2637(6) 0.0292(15) Uani 1 1 d . . . . .
Nd1 Nd 0.54682(4) 0.43199(3) 0.35830(3) 0.02728(14) Uani 1 1 d . . . . .
N1 N 0.7415(6) 0.6152(5) 0.3528(5) 0.0278(12) Uani 1 1 d . . . . .
N2 N 0.4446(7) 0.4919(5) 0.1696(5) 0.0309(13) Uani 1 1 d . . . . .
O1 O 0.9787(5) 0.4977(4) 0.7348(4) 0.0328(11) Uani 1 1 d . . . . .
O2 O 0.7496(5) 0.5769(4) 0.7037(4) 0.0301(10) Uani 1 1 d . . . . .
O3 O 0.7953(5) 0.4645(4) 0.5327(4) 0.0310(10) Uani 1 1 d . . . . .
O4 O 0.4109(7) 0.0655(4) 0.0714(5) 0.0496(14) Uani 1 1 d . . . . .
O5 O 0.4178(6) 0.2229(4) 0.2401(4) 0.0383(12) Uani 1 1 d . . . . .
O6 O 0.1731(6) 0.0609(4) 0.1099(5) 0.0480(14) Uani 1 1 d . . . . .
O7 O 0.4749(5) 0.3858(3) 0.5087(4) 0.0242(9) Uani 1 1 d . . . . .
O8 O 0.7352(6) 0.3609(4) 0.2778(5) 0.0428(13) Uani 1 1 d D . . . .
H8A H 0.808(7) 0.406(6) 0.272(8) 0.064 Uiso 1 1 d DR . . . .
H8B H 0.718(10) 0.287(3) 0.241(7) 0.064 Uiso 1 1 d DR . . . .
O9 O 0.7604(8) 0.1484(6) 0.1599(6) 0.0723(19) Uani 1 1 d . . . . .
H9A H 0.8048 0.1668 0.1164 0.108 Uiso 1 1 d G . . . .
H9B H 0.6735 0.0910 0.1156 0.108 Uiso 1 1 d G . . . .
S1 S 0.81541(19) 0.47984(14) 0.65639(15) 0.0258(4) Uani 1 1 d . . . . .
S2 S 0.3455(2) 0.09445(14) 0.15946(15) 0.0294(4) Uani 1 1 d . . . . .
O10 O 0.9767(8) 0.2207(6) 0.0684(7) 0.078(2) Uani 1 1 d . . . . .
H10A H 0.9882 0.1513 0.0673 0.117 Uiso 1 1 d G . . . .
H10B H 1.0563 0.2764 0.1270 0.117 Uiso 1 1 d G . . . .
O11 O 1.0358(12) 0.0797(10) 0.2955(9) 0.108(3) Uani 1 1 d . . . . .
H11A H 1.0819 0.0776 0.2480 0.163 Uiso 1 1 d G . . . .
H11B H 0.9616 0.1135 0.2780 0.163 Uiso 1 1 d G . . . .


_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
C1 C2 1.369(8) . ?
C1 C10 1.425(9) . ?
C1 S1 1.777(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.420(9) . ?
C3 C4 1.415(8) . ?
C3 C8 1.424(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.358(9) . ?
C5 C6 1.404(9) . ?
C5 S2 1.768(6) 2_656 ?
C6 H6 0.9300 . ?
C6 C7 1.372(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.417(9) . ?
C8 C9 1.408(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(8) . ?
C10 O7 1.352(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(10) . ?
C11 N1 1.326(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.364(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.410(10) . ?
C14 C15 1.421(10) . ?
C14 C22 1.412(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.345(11) . ?
C16 H16 0.9300 . ?
C16 C17 1.432(10) . ?
C17 C18 1.395(11) . ?
C17 C21 1.397(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(11) . ?
C19 H19 0.9300 . ?
C19 C20 1.404(10) . ?
C20 H20 0.9300 . ?
C20 N2 1.339(9) . ?
C21 C22 1.423(9) . ?
C21 N2 1.363(8) . ?
C22 N1 1.372(8) . ?
Nd1 Nd1 3.9631(7) 2_666 ?
Nd1 N1 2.636(5) . ?
Nd1 N2 2.614(5) . ?
Nd1 O2 2.557(4) 2_666 ?
Nd1 O3 2.465(4) . ?
Nd1 O5 2.362(4) . ?
Nd1 O7 2.433(4) 2_666 ?
Nd1 O7 2.407(4) . ?
Nd1 O8 2.458(5) . ?
O1 S1 1.436(4) . ?
O2 Nd1 2.557(4) 2_666 ?
O2 S1 1.471(4) . ?
O3 S1 1.475(5) . ?
O4 S2 1.436(5) . ?
O5 S2 1.466(4) . ?
O6 S2 1.436(5) . ?
O7 Nd1 2.433(4) 2_666 ?
O8 H8A 0.83(2) . ?
O8 H8B 0.83(2) . ?
O9 H9A 0.8496 . ?
O9 H9B 0.8501 . ?
S2 C5 1.768(6) 2_656 ?
O10 H10A 0.8499 . ?
O10 H10B 0.8499 . ?
O11 H11A 0.8500 . ?
O11 H11B 0.8495 . ?

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
C2 C1 C10 123.0(6) . . ?
C2 C1 S1 121.6(5) . . ?
C10 C1 S1 115.4(4) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.9(6) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C8 118.6(5) . . ?
C4 C3 C2 122.5(6) . . ?
C4 C3 C8 118.9(6) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.9(6) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.9(6) . . ?
C4 C5 S2 120.3(5) . 2_656 ?
C6 C5 S2 118.7(5) . 2_656 ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.7(6) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.2(6) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C3 118.4(6) . . ?
C9 C8 C3 120.2(6) . . ?
C9 C8 C7 121.4(6) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(6) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C1 117.9(5) . . ?
O7 C10 C1 119.2(5) . . ?
O7 C10 C9 122.8(6) . . ?
C12 C11 H11 118.4 . . ?
N1 C11 H11 118.4 . . ?
N1 C11 C12 123.3(7) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.1(7) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(7) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 122.4(7) . . ?
C13 C14 C22 117.6(6) . . ?
C22 C14 C15 120.0(7) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(7) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.1(7) . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 122.5(7) . . ?
C18 C17 C21 117.5(7) . . ?
C21 C17 C16 120.0(7) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(7) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.8 . . ?
C18 C19 C20 118.4(7) . . ?
C20 C19 H19 120.8 . . ?
C19 C20 H20 118.8 . . ?
N2 C20 C19 122.4(7) . . ?
N2 C20 H20 118.8 . . ?
C17 C21 C22 119.0(6) . . ?
N2 C21 C17 122.6(6) . . ?
N2 C21 C22 118.4(6) . . ?
C14 C22 C21 119.6(6) . . ?
N1 C22 C14 121.5(6) . . ?
N1 C22 C21 118.9(5) . . ?
N1 Nd1 Nd1 106.28(11) . 2_666 ?
N2 Nd1 Nd1 122.19(12) . 2_666 ?
N2 Nd1 N1 62.80(17) . . ?
O2 Nd1 Nd1 68.43(10) 2_666 2_666 ?
O2 Nd1 N1 118.43(14) 2_666 . ?
O2 Nd1 N2 70.05(15) 2_666 . ?
O3 Nd1 Nd1 75.31(10) . 2_666 ?
O3 Nd1 N1 79.31(15) . . ?
O3 Nd1 N2 141.03(15) . . ?
O3 Nd1 O2 142.76(14) . 2_666 ?
O5 Nd1 Nd1 116.54(12) . 2_666 ?
O5 Nd1 N1 137.15(16) . . ?
O5 Nd1 N2 91.59(16) . . ?
O5 Nd1 O2 78.12(15) . 2_666 ?
O5 Nd1 O3 112.16(15) . . ?
O5 Nd1 O7 85.08(15) . . ?
O5 Nd1 O7 144.34(16) . 2_666 ?
O5 Nd1 O8 74.94(17) . . ?
O7 Nd1 Nd1 34.82(9) 2_666 2_666 ?
O7 Nd1 Nd1 35.25(9) . 2_666 ?
O7 Nd1 N1 136.07(15) . . ?
O7 Nd1 N1 75.17(14) 2_666 . ?
O7 Nd1 N2 143.91(15) . . ?
O7 Nd1 N2 93.91(15) 2_666 . ?
O7 Nd1 O2 70.85(13) 2_666 2_666 ?
O7 Nd1 O2 74.11(13) . 2_666 ?
O7 Nd1 O3 84.36(14) 2_666 . ?
O7 Nd1 O3 71.44(14) . . ?
O7 Nd1 O7 70.08(14) . 2_666 ?
O7 Nd1 O8 140.65(15) 2_666 . ?
O7 Nd1 O8 128.53(16) . . ?
O8 Nd1 Nd1 148.55(14) . 2_666 ?
O8 Nd1 N1 69.22(16) . . ?
O8 Nd1 N2 84.51(18) . . ?
O8 Nd1 O2 142.12(16) . 2_666 ?
O8 Nd1 O3 73.28(17) . . ?
C11 N1 C22 118.6(5) . . ?
C11 N1 Nd1 122.3(4) . . ?
C22 N1 Nd1 118.6(4) . . ?
C20 N2 C21 118.3(6) . . ?
C20 N2 Nd1 121.1(4) . . ?
C21 N2 Nd1 119.8(4) . . ?
S1 O2 Nd1 127.1(2) . 2_666 ?
S1 O3 Nd1 128.0(2) . . ?
S2 O5 Nd1 174.6(3) . . ?
C10 O7 Nd1 115.0(3) . 2_666 ?
C10 O7 Nd1 124.9(3) . . ?
Nd1 O7 Nd1 109.92(14) . 2_666 ?
Nd1 O8 H8A 124(6) . . ?
Nd1 O8 H8B 120(6) . . ?
H8A O8 H8B 114(8) . . ?
H9A O9 H9B 109.5 . . ?
O1 S1 C1 109.3(3) . . ?
O1 S1 O2 112.5(3) . . ?
O1 S1 O3 112.5(3) . . ?
O2 S1 C1 106.2(3) . . ?
O2 S1 O3 110.8(2) . . ?
O3 S1 C1 105.1(3) . . ?
O4 S2 C5 106.9(3) . 2_656 ?
O4 S2 O5 110.9(3) . . ?
O5 S2 C5 105.0(3) . 2_656 ?
O6 S2 C5 107.1(3) . 2_656 ?
O6 S2 O4 114.3(3) . . ?
O6 S2 O5 112.0(3) . . ?
H10A O10 H10B 109.5 . . ?
H11A O11 H11B 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
C1 C2 C3 C4 -176.4(6) . . . . ?
C1 C2 C3 C8 2.2(9) . . . . ?
C1 C10 O7 Nd1 -71.8(6) . . . 2_666 ?
C1 C10 O7 Nd1 69.8(6) . . . . ?
C2 C1 C10 C9 -3.9(9) . . . . ?
C2 C1 C10 O7 174.1(5) . . . . ?
C2 C1 S1 O1 4.5(6) . . . . ?
C2 C1 S1 O2 -117.1(5) . . . . ?
C2 C1 S1 O3 125.5(5) . . . . ?
C2 C3 C4 C5 178.4(6) . . . . ?
C2 C3 C8 C7 -179.5(6) . . . . ?
C2 C3 C8 C9 -1.9(9) . . . . ?
C3 C4 C5 C6 1.0(10) . . . . ?
C3 C4 C5 S2 -176.0(5) . . . 2_656 ?
C3 C8 C9 C10 -1.4(9) . . . . ?
C4 C3 C8 C7 -0.8(9) . . . . ?
C4 C3 C8 C9 176.8(6) . . . . ?
C4 C5 C6 C7 -0.5(10) . . . . ?
C5 C6 C7 C8 -0.7(10) . . . . ?
C6 C7 C8 C3 1.3(10) . . . . ?
C6 C7 C8 C9 -176.3(6) . . . . ?
C7 C8 C9 C10 176.1(6) . . . . ?
C8 C3 C4 C5 -0.3(10) . . . . ?
C8 C9 C10 C1 4.2(9) . . . . ?
C8 C9 C10 O7 -173.7(5) . . . . ?
C9 C10 O7 Nd1 106.1(6) . . . 2_666 ?
C9 C10 O7 Nd1 -112.3(6) . . . . ?
C10 C1 C2 C3 0.7(9) . . . . ?
C10 C1 S1 O1 -176.3(4) . . . . ?
C10 C1 S1 O2 62.1(5) . . . . ?
C10 C1 S1 O3 -55.3(5) . . . . ?
C11 C12 C13 C14 -0.1(12) . . . . ?
C12 C11 N1 C22 -0.7(10) . . . . ?
C12 C11 N1 Nd1 -172.5(6) . . . . ?
C12 C13 C14 C15 177.8(7) . . . . ?
C12 C13 C14 C22 -0.9(11) . . . . ?
C13 C14 C15 C16 -176.6(7) . . . . ?
C13 C14 C22 C21 180.0(6) . . . . ?
C13 C14 C22 N1 1.1(10) . . . . ?
C14 C15 C16 C17 -2.6(12) . . . . ?
C14 C22 N1 C11 -0.3(9) . . . . ?
C14 C22 N1 Nd1 171.8(5) . . . . ?
C15 C14 C22 C21 1.2(10) . . . . ?
C15 C14 C22 N1 -177.7(6) . . . . ?
C15 C16 C17 C18 -179.1(8) . . . . ?
C15 C16 C17 C21 -0.2(11) . . . . ?
C16 C17 C18 C19 176.6(8) . . . . ?
C16 C17 C21 C22 3.5(10) . . . . ?
C16 C17 C21 N2 -178.5(7) . . . . ?
C17 C18 C19 C20 0.4(12) . . . . ?
C17 C21 C22 C14 -3.9(9) . . . . ?
C17 C21 C22 N1 175.0(6) . . . . ?
C17 C21 N2 C20 3.4(10) . . . . ?
C17 C21 N2 Nd1 -166.0(5) . . . . ?
C18 C17 C21 C22 -177.6(6) . . . . ?
C18 C17 C21 N2 0.4(10) . . . . ?
C18 C19 C20 N2 3.7(12) . . . . ?
C19 C20 N2 C21 -5.5(10) . . . . ?
C19 C20 N2 Nd1 163.8(5) . . . . ?
C21 C17 C18 C19 -2.3(11) . . . . ?
C21 C22 N1 C11 -179.2(6) . . . . ?
C21 C22 N1 Nd1 -7.1(7) . . . . ?
C22 C14 C15 C16 2.1(11) . . . . ?
C22 C21 N2 C20 -178.5(6) . . . . ?
C22 C21 N2 Nd1 12.1(8) . . . . ?
Nd1 O2 S1 C1 -41.5(4) 2_666 . . . ?
Nd1 O2 S1 O1 -161.0(3) 2_666 . . . ?
Nd1 O2 S1 O3 72.1(3) 2_666 . . . ?
Nd1 O3 S1 C1 61.5(4) . . . . ?
Nd1 O3 S1 O1 -179.7(3) . . . . ?
Nd1 O3 S1 O2 -52.8(4) . . . . ?
N1 C11 C12 C13 0.9(12) . . . . ?
N2 C21 C22 C14 177.9(6) . . . . ?
N2 C21 C22 N1 -3.2(9) . . . . ?
S1 C1 C2 C3 179.8(5) . . . . ?
S1 C1 C10 C9 176.9(5) . . . . ?
S1 C1 C10 O7 -5.1(7) . . . . ?
S2 C5 C6 C7 176.6(5) 2_656 . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_Compound5
_database_code_depnum_ccdc_archive 'CCDC 1426617'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;
_audit_creation_date             2015-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 La N2 O8 S2, 3(H2 O)'
_chemical_formula_sum            'C22 H21 La N2 O11 S2'
_chemical_formula_weight         692.44
_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'
La La -0.2871 2.4523 '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'
S S 0.1246 0.1234 '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      triclinic
_space_group_IT_number           2
_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                   9.2906(14)
_cell_length_b                   12.025(2)
_cell_length_c                   12.835(2)
_cell_angle_alpha                106.491(8)
_cell_angle_beta                 110.125(9)
_cell_angle_gamma                99.551(9)
_cell_volume                     1234.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    1.965
_exptl_absorpt_correction_T_max  0.803
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst.
   (1965), 18, 1035-1038
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method Hydrothermal
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1021
_diffrn_reflns_av_unetI/netI     0.1072
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31308
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.421
_diffrn_reflns_theta_min         2.973
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3179
_reflns_number_total             4997
_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_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_refine_diff_density_max         1.203
_refine_diff_density_min         -0.909
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4997
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      0.861
_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)+(0.0357P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0831
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O8-H8A = O8-H8B
 0.84 with sigma of 0.02
3.a Free rotating group:
 O9(H9A,H9B), O10(H10A,H10B), O11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C1 C 0.6949(5) 0.3437(4) 0.6450(4) 0.0350(11) Uani 1 1 d . . . . .
C2 C 0.7508(5) 0.2750(4) 0.7082(4) 0.0368(12) Uani 1 1 d . . . . .
H2 H 0.8581 0.3000 0.7612 0.044 Uiso 1 1 calc R . . . .
C3 C 0.6486(5) 0.1664(4) 0.6948(4) 0.0374(12) Uani 1 1 d . . . . .
C4 C 0.6985(6) 0.0953(4) 0.7634(4) 0.0417(12) Uani 1 1 d . . . . .
H4 H 0.8041 0.1195 0.8193 0.050 Uiso 1 1 calc R . . . .
C5 C 0.5951(6) -0.0076(4) 0.7494(4) 0.0372(12) Uani 1 1 d . . . . .
C6 C 0.4340(6) -0.0459(5) 0.6642(4) 0.0475(13) Uani 1 1 d . . . . .
H6 H 0.3630 -0.1163 0.6545 0.057 Uiso 1 1 calc R . . . .
C7 C 0.3835(6) 0.0202(5) 0.5970(4) 0.0443(13) Uani 1 1 d . . . . .
H7 H 0.2780 -0.0068 0.5404 0.053 Uiso 1 1 calc R . . . .
C8 C 0.4857(5) 0.1283(4) 0.6099(4) 0.0356(11) Uani 1 1 d . . . . .
C9 C 0.4310(5) 0.1992(4) 0.5448(4) 0.0369(12) Uani 1 1 d . . . . .
H9 H 0.3256 0.1723 0.4880 0.044 Uiso 1 1 calc R . . . .
C10 C 0.5292(5) 0.3080(4) 0.5627(4) 0.0334(11) Uani 1 1 d . . . . .
C11 C 0.8890(6) 0.6756(5) 0.4366(5) 0.0524(14) Uani 1 1 d . . . . .
H11 H 0.9281 0.6445 0.4957 0.063 Uiso 1 1 calc R . . . .
C12 C 0.9853(6) 0.7808(5) 0.4434(5) 0.0615(16) Uani 1 1 d . . . . .
H12 H 1.0865 0.8186 0.5058 0.074 Uiso 1 1 calc R . . . .
C13 C 0.9308(7) 0.8289(5) 0.3580(5) 0.0602(16) Uani 1 1 d . . . . .
H13 H 0.9942 0.8998 0.3620 0.072 Uiso 1 1 calc R . . . .
C14 C 0.7774(6) 0.7698(5) 0.2639(5) 0.0508(14) Uani 1 1 d . . . . .
C15 C 0.7096(8) 0.8152(5) 0.1719(5) 0.0637(17) Uani 1 1 d . . . . .
H15 H 0.7707 0.8837 0.1704 0.076 Uiso 1 1 calc R . . . .
C16 C 0.5611(8) 0.7609(6) 0.0891(5) 0.0643(17) Uani 1 1 d . . . . .
H16 H 0.5182 0.7950 0.0334 0.077 Uiso 1 1 calc R . . . .
C17 C 0.4652(7) 0.6515(5) 0.0831(4) 0.0502(14) Uani 1 1 d . . . . .
C18 C 0.3096(7) 0.5913(6) -0.0042(5) 0.0625(16) Uani 1 1 d . . . . .
H18 H 0.2622 0.6238 -0.0604 0.075 Uiso 1 1 calc R . . . .
C19 C 0.2268(7) 0.4844(6) -0.0070(5) 0.0620(16) Uani 1 1 d . . . . .
H19 H 0.1232 0.4435 -0.0651 0.074 Uiso 1 1 calc R . . . .
C20 C 0.3005(6) 0.4369(5) 0.0794(4) 0.0530(15) Uani 1 1 d . . . . .
H20 H 0.2461 0.3623 0.0749 0.064 Uiso 1 1 calc R . . . .
C21 C 0.5305(6) 0.6009(5) 0.1688(4) 0.0410(12) Uani 1 1 d . . . . .
C22 C 0.6871(6) 0.6628(5) 0.2622(4) 0.0405(12) Uani 1 1 d . . . . .
La1 La 0.54795(3) 0.42974(3) 0.35636(2) 0.03720(11) Uani 1 1 d . . . . .
N1 N 0.7429(5) 0.6165(4) 0.3495(3) 0.0415(10) Uani 1 1 d . . . . .
N2 N 0.4454(5) 0.4956(4) 0.1671(3) 0.0415(10) Uani 1 1 d . . . . .
O1 O 0.9803(3) 0.4977(3) 0.7378(3) 0.0422(8) Uani 1 1 d . . . . .
O2 O 0.7524(3) 0.5768(3) 0.7059(3) 0.0397(8) Uani 1 1 d . . . . .
O3 O 0.8006(3) 0.4659(3) 0.5371(3) 0.0410(8) Uani 1 1 d . . . . .
O4 O 0.4106(5) 0.0610(3) 0.0710(3) 0.0629(11) Uani 1 1 d . . . . .
O5 O 0.4161(4) 0.2184(3) 0.2370(3) 0.0522(9) Uani 1 1 d . . . . .
O6 O 0.1723(4) 0.0549(3) 0.1078(3) 0.0618(11) Uani 1 1 d . . . . .
O7 O 0.4767(3) 0.3853(3) 0.5112(2) 0.0343(7) Uani 1 1 d . . . . .
O8 O 0.7445(5) 0.3593(4) 0.2782(3) 0.0555(10) Uani 1 1 d D . . . .
H8A H 0.807(6) 0.417(4) 0.279(5) 0.083 Uiso 1 1 d DR . . . .
H8B H 0.741(7) 0.295(3) 0.228(4) 0.083 Uiso 1 1 d DR . . . .
O9 O 0.7631(5) 0.1475(4) 0.1600(4) 0.0888(14) Uani 1 1 d . . . . .
H9A H 0.7934 0.1539 0.1058 0.133 Uiso 1 1 d G . . . .
H9B H 0.6795 0.0870 0.1292 0.133 Uiso 1 1 d G . . . .
S1 S 0.81795(14) 0.48046(11) 0.65933(10) 0.0372(3) Uani 1 1 d . . . . .
S2 S 0.34471(15) 0.08996(12) 0.15746(11) 0.0421(3) Uani 1 1 d . . . . .
O10 O 0.9807(6) 0.2188(5) 0.0697(5) 0.0915(14) Uani 1 1 d . . . . .
H10A H 1.0005 0.1503 0.0572 0.137 Uiso 1 1 d G . . . .
H10B H 1.0528 0.2706 0.1359 0.137 Uiso 1 1 d G . . . .
O11 O 1.0404(8) 0.0847(8) 0.2975(6) 0.150(2) Uani 1 1 d . . . . .
H11A H 1.0874 0.1294 0.2706 0.225 Uiso 1 1 d G . . . .
H11B H 0.9401 0.0580 0.2527 0.225 Uiso 1 1 d G . . . .


_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
C1 C2 1.358(6) . ?
C1 C10 1.440(6) . ?
C1 S1 1.762(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.409(6) . ?
C3 C4 1.414(6) . ?
C3 C8 1.428(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.359(6) . ?
C5 C6 1.417(6) . ?
C5 S2 1.766(5) 2_656 ?
C6 H6 0.9300 . ?
C6 C7 1.352(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.407(6) . ?
C8 C9 1.392(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(6) . ?
C10 O7 1.347(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(7) . ?
C11 N1 1.335(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.366(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.410(7) . ?
C14 C15 1.433(7) . ?
C14 C22 1.405(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.326(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.427(7) . ?
C17 C18 1.395(7) . ?
C17 C21 1.411(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.369(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.411(7) . ?
C20 H20 0.9300 . ?
C20 N2 1.330(6) . ?
C21 C22 1.428(7) . ?
C21 N2 1.367(6) . ?
C22 N1 1.373(6) . ?
La1 La1 4.0581(8) 2_666 ?
La1 N1 2.684(4) . ?
La1 N2 2.681(4) . ?
La1 O2 2.606(3) 2_666 ?
La1 O3 2.534(3) . ?
La1 O5 2.403(3) . ?
La1 O7 2.485(3) 2_666 ?
La1 O7 2.463(3) . ?
La1 O8 2.520(3) . ?
O1 S1 1.437(3) . ?
O2 La1 2.606(3) 2_666 ?
O2 S1 1.470(3) . ?
O3 S1 1.476(3) . ?
O4 S2 1.430(3) . ?
O5 S2 1.472(3) . ?
O6 S2 1.439(3) . ?
O7 La1 2.485(3) 2_666 ?
O8 H8A 0.827(19) . ?
O8 H8B 0.84(2) . ?
O9 H9A 0.8533 . ?
O9 H9B 0.8527 . ?
S2 C5 1.766(5) 2_656 ?
O10 H10A 0.8557 . ?
O10 H10B 0.8536 . ?
O11 H11A 0.8543 . ?
O11 H11B 0.8542 . ?

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
C2 C1 C10 121.0(4) . . ?
C2 C1 S1 122.6(4) . . ?
C10 C1 S1 116.4(3) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 123.1(4) . . ?
C2 C3 C8 118.2(4) . . ?
C4 C3 C8 118.6(4) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 S2 120.8(4) . 2_656 ?
C6 C5 S2 119.1(4) . 2_656 ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.8(5) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.0 . . ?
C6 C7 C8 122.1(5) . . ?
C8 C7 H7 119.0 . . ?
C7 C8 C3 118.2(4) . . ?
C9 C8 C3 120.0(4) . . ?
C9 C8 C7 121.8(4) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.5(4) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C1 118.2(4) . . ?
O7 C10 C1 118.4(4) . . ?
O7 C10 C9 123.3(4) . . ?
C12 C11 H11 118.3 . . ?
N1 C11 H11 118.3 . . ?
N1 C11 C12 123.4(5) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(5) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.3(5) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C15 122.9(5) . . ?
C22 C14 C13 117.9(5) . . ?
C22 C14 C15 119.1(5) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(5) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.1 . . ?
C15 C16 C17 121.9(5) . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 123.1(5) . . ?
C18 C17 C21 118.2(5) . . ?
C21 C17 C16 118.7(5) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.9(5) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.2(5) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 119.0 . . ?
N2 C20 C19 122.1(5) . . ?
N2 C20 H20 119.0 . . ?
C17 C21 C22 119.5(5) . . ?
N2 C21 C17 121.5(5) . . ?
N2 C21 C22 118.9(4) . . ?
C14 C22 C21 119.6(5) . . ?
N1 C22 C14 122.0(5) . . ?
N1 C22 C21 118.3(4) . . ?
N1 La1 La1 105.74(8) . 2_666 ?
N2 La1 La1 120.88(9) . 2_666 ?
N2 La1 N1 61.45(12) . . ?
O2 La1 La1 68.13(7) 2_666 2_666 ?
O2 La1 N1 117.02(11) 2_666 . ?
O2 La1 N2 69.70(10) 2_666 . ?
O3 La1 La1 74.38(7) . 2_666 ?
O3 La1 N1 80.05(11) . . ?
O3 La1 N2 140.83(11) . . ?
O3 La1 O2 141.71(9) . 2_666 ?
O5 La1 La1 116.86(8) . 2_666 ?
O5 La1 N1 137.31(11) . . ?
O5 La1 N2 92.67(12) . . ?
O5 La1 O2 78.65(11) . 2_666 ?
O5 La1 O3 113.00(11) . . ?
O5 La1 O7 85.88(10) . . ?
O5 La1 O7 144.01(10) . 2_666 ?
O5 La1 O8 75.65(12) . . ?
O7 La1 La1 34.72(6) 2_666 2_666 ?
O7 La1 La1 35.09(7) . 2_666 ?
O7 La1 N1 135.40(11) . . ?
O7 La1 N1 74.77(10) 2_666 . ?
O7 La1 N2 143.90(11) . . ?
O7 La1 N2 92.14(11) 2_666 . ?
O7 La1 O2 69.73(9) 2_666 2_666 ?
O7 La1 O2 74.68(9) . 2_666 ?
O7 La1 O3 83.99(10) 2_666 . ?
O7 La1 O3 70.24(9) . . ?
O7 La1 O7 69.80(11) . 2_666 ?
O7 La1 O8 140.30(11) 2_666 . ?
O7 La1 O8 128.15(12) . . ?
O8 La1 La1 147.78(9) . 2_666 ?
O8 La1 N1 69.53(12) . . ?
O8 La1 N2 85.84(12) . . ?
O8 La1 O2 143.40(11) . 2_666 ?
O8 La1 O3 73.42(11) . . ?
C11 N1 C22 117.8(4) . . ?
C11 N1 La1 121.7(3) . . ?
C22 N1 La1 120.1(3) . . ?
C20 N2 C21 119.0(4) . . ?
C20 N2 La1 120.3(3) . . ?
C21 N2 La1 119.9(3) . . ?
S1 O2 La1 127.65(17) . 2_666 ?
S1 O3 La1 128.14(16) . . ?
S2 O5 La1 174.6(2) . . ?
C10 O7 La1 116.1(2) . 2_666 ?
C10 O7 La1 124.3(2) . . ?
La1 O7 La1 110.20(11) . 2_666 ?
La1 O8 H8A 111(4) . . ?
La1 O8 H8B 134(4) . . ?
H8A O8 H8B 109(6) . . ?
H9A O9 H9B 109.1 . . ?
O1 S1 C1 109.1(2) . . ?
O1 S1 O2 112.59(19) . . ?
O1 S1 O3 112.07(18) . . ?
O2 S1 C1 106.39(19) . . ?
O2 S1 O3 111.02(18) . . ?
O3 S1 C1 105.3(2) . . ?
O4 S2 C5 107.0(2) . 2_656 ?
O4 S2 O5 111.1(2) . . ?
O4 S2 O6 114.3(2) . . ?
O5 S2 C5 105.1(2) . 2_656 ?
O6 S2 C5 106.4(2) . 2_656 ?
O6 S2 O5 112.1(2) . . ?
H10A O10 H10B 109.5 . . ?
H11A O11 H11B 109.4 . . ?

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
C1 C2 C3 C4 -176.2(4) . . . . ?
C1 C2 C3 C8 2.0(7) . . . . ?
C1 C10 O7 La1 -71.4(4) . . . 2_666 ?
C1 C10 O7 La1 71.6(5) . . . . ?
C2 C1 C10 C9 -3.6(6) . . . . ?
C2 C1 C10 O7 173.5(4) . . . . ?
C2 C1 S1 O1 4.7(4) . . . . ?
C2 C1 S1 O2 -117.0(4) . . . . ?
C2 C1 S1 O3 125.1(4) . . . . ?
C2 C3 C4 C5 178.6(4) . . . . ?
C2 C3 C8 C7 -179.7(4) . . . . ?
C2 C3 C8 C9 -1.2(6) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C3 C4 C5 S2 -175.7(3) . . . 2_656 ?
C3 C8 C9 C10 -2.0(7) . . . . ?
C4 C3 C8 C7 -1.4(6) . . . . ?
C4 C3 C8 C9 177.1(4) . . . . ?
C4 C5 C6 C7 0.1(7) . . . . ?
C5 C6 C7 C8 -1.1(7) . . . . ?
C6 C7 C8 C3 1.8(7) . . . . ?
C6 C7 C8 C9 -176.6(5) . . . . ?
C7 C8 C9 C10 176.3(4) . . . . ?
C8 C3 C4 C5 0.4(7) . . . . ?
C8 C9 C10 C1 4.4(6) . . . . ?
C8 C9 C10 O7 -172.6(4) . . . . ?
C9 C10 O7 La1 105.6(4) . . . 2_666 ?
C9 C10 O7 La1 -111.4(4) . . . . ?
C10 C1 C2 C3 0.4(7) . . . . ?
C10 C1 S1 O1 -175.9(3) . . . . ?
C10 C1 S1 O2 62.4(4) . . . . ?
C10 C1 S1 O3 -55.5(4) . . . . ?
C11 C12 C13 C14 -0.4(8) . . . . ?
C12 C11 N1 C22 0.5(8) . . . . ?
C12 C11 N1 La1 -172.0(4) . . . . ?
C12 C13 C14 C15 178.7(5) . . . . ?
C12 C13 C14 C22 -0.2(8) . . . . ?
C13 C14 C15 C16 -175.8(6) . . . . ?
C13 C14 C22 C21 179.4(5) . . . . ?
C13 C14 C22 N1 1.0(7) . . . . ?
C14 C15 C16 C17 -3.7(9) . . . . ?
C14 C22 N1 C11 -1.2(7) . . . . ?
C14 C22 N1 La1 171.5(4) . . . . ?
C15 C14 C22 C21 0.5(7) . . . . ?
C15 C14 C22 N1 -178.0(5) . . . . ?
C15 C16 C17 C18 -178.9(6) . . . . ?
C15 C16 C17 C21 0.7(8) . . . . ?
C16 C17 C18 C19 177.7(5) . . . . ?
C16 C17 C21 C22 2.8(7) . . . . ?
C16 C17 C21 N2 -179.4(5) . . . . ?
C17 C18 C19 C20 0.3(8) . . . . ?
C17 C21 C22 C14 -3.4(7) . . . . ?
C17 C21 C22 N1 175.1(4) . . . . ?
C17 C21 N2 C20 3.1(7) . . . . ?
C17 C21 N2 La1 -166.8(3) . . . . ?
C18 C17 C21 C22 -177.5(5) . . . . ?
C18 C17 C21 N2 0.3(7) . . . . ?
C18 C19 C20 N2 3.2(8) . . . . ?
C19 C20 N2 C21 -4.9(7) . . . . ?
C19 C20 N2 La1 165.0(4) . . . . ?
C21 C17 C18 C19 -2.0(8) . . . . ?
C21 C22 N1 C11 -179.6(4) . . . . ?
C21 C22 N1 La1 -6.9(6) . . . . ?
C22 C14 C15 C16 3.1(8) . . . . ?
C22 C21 N2 C20 -179.1(4) . . . . ?
C22 C21 N2 La1 11.0(6) . . . . ?
La1 O2 S1 C1 -41.5(3) 2_666 . . . ?
La1 O2 S1 O1 -160.86(18) 2_666 . . . ?
La1 O2 S1 O3 72.6(2) 2_666 . . . ?
La1 O3 S1 C1 60.6(3) . . . . ?
La1 O3 S1 O1 179.0(2) . . . . ?
La1 O3 S1 O2 -54.1(3) . . . . ?
N1 C11 C12 C13 0.2(9) . . . . ?
N2 C21 C22 C14 178.8(4) . . . . ?
N2 C21 C22 N1 -2.7(7) . . . . ?
S1 C1 C2 C3 179.7(3) . . . . ?
S1 C1 C10 C9 177.0(3) . . . . ?
S1 C1 C10 O7 -5.8(5) . . . . ?
S2 C5 C6 C7 176.2(4) 2_656 . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       Luminescent
