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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_thc1
_database_code_depnum_ccdc_archive 'CCDC 1547972'
_audit_update_record             
;
2017-07-03 deposited with the CCDC.
2017-07-12 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            'C15 H26 La2 O22 P3 S3'
_chemical_formula_weight         1025.27

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'
P P 0.1023 0.0942 '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'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

_cell_length_a                   20.047(4)
_cell_length_b                   11.357(2)
_cell_length_c                   18.677(4)
_cell_angle_alpha                90
_cell_angle_beta                 118.51(3)
_cell_angle_gamma                90
_cell_volume                     3736.3(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    26130
_cell_measurement_theta_min      4.07
_cell_measurement_theta_max      56.01

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_F_000             1996
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1333
_exptl_crystal_size_mid          0.1059
_exptl_crystal_size_min          0.0603
_exptl_absorpt_coefficient_mu    2.626
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6378
_exptl_absorpt_correction_T_max  0.8019
_exptl_absorpt_process_details   'X-RED and X-SHAPE (STOE, 2008)'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS-2'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19490
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.036
_diffrn_reflns_theta_max         27.449
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4470
_reflns_number_gt                3990
_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       'X-AREA (STOE, 2008)'
_computing_cell_refinement       'X-AREA (STOE, 2008)'
_computing_data_reduction        'X-AREA (STOE, 2008)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond (Brandenburg, 1999)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+130.8599P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4470
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1685
_refine_ls_wR_factor_gt          0.1654
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
La1 La 0.80074(4) 0.5000 0.69994(4) 0.03173(18) Uani 1 2 d S T P A .
La2 La 0.77987(4) 0.0000 0.68406(4) 0.03557(19) Uani 1 2 d S T P A .
O1 O 0.6987(5) 0.5000 0.5458(5) 0.046(2) Uani 1 2 d S T P . .
O2 O 0.6799(6) 0.0000 0.5264(6) 0.053(2) Uani 1 2 d S T P . .
O3 O 0.7607(10) 0.0000 0.8162(10) 0.096(5) Uani 1 2 d S T P . .
O4 O 0.7811(10) 0.5000 0.8323(9) 0.097(5) Uani 1 2 d S T P . .
S1 S 0.65849(12) 0.25291(19) 0.67967(14) 0.0361(4) Uani 0.5 1 d . . P A 1
P1 P 0.65849(12) 0.25291(19) 0.67967(14) 0.0361(4) Uani 0.5 1 d . . P A 2
O5 O 0.6816(3) 0.1386(6) 0.6590(5) 0.0550(18) Uani 1 1 d . . . . .
O6 O 0.7081(3) 0.3513(6) 0.6857(5) 0.0525(17) Uani 1 1 d . . . . .
O7 O 0.6530(4) 0.2385(8) 0.7571(4) 0.063(2) Uani 1 1 d . . . . .
C1 C 0.5648(4) 0.2822(7) 0.6007(5) 0.0356(17) Uani 1 1 d . . . . .
H1B H 0.5654 0.2909 0.5483 0.043 Uiso 1 1 calc R U . A 1
H1A H 0.5315 0.2148 0.5956 0.043 Uiso 1 1 calc R U . A 1
C2 C 0.5335(4) 0.3918(7) 0.6177(5) 0.0322(16) Uani 1 1 d . . . . .
C3 C 0.5537(6) 0.5000 0.5984(7) 0.034(2) Uani 1 2 d S T P . .
H3 H 0.5829 0.5000 0.5706 0.041 Uiso 1 2 calc R U P . .
C4 C 0.4694(6) 0.5000 0.6783(7) 0.030(2) Uani 1 2 d S T P . .
H4 H 0.4415 0.5000 0.7075 0.036 Uiso 1 2 calc R U P . .
C5 C 0.4895(4) 0.3922(7) 0.6573(5) 0.0313(15) Uani 1 1 d . . . . .
C6 C 0.4602(5) 0.2813(7) 0.6762(5) 0.0372(17) Uani 1 1 d . . . . .
H6B H 0.4665 0.2868 0.7320 0.045 Uiso 1 1 calc R U . B 1
H6A H 0.4907 0.2137 0.6748 0.045 Uiso 1 1 calc R U . B 1
S2 S 0.36183(12) 0.25539(19) 0.60548(13) 0.0366(4) Uani 0.5 1 d . . P C 1
P2 P 0.36183(12) 0.25539(19) 0.60548(13) 0.0366(4) Uani 0.5 1 d . . P C 2
O8 O 0.3398(4) 0.1406(6) 0.6250(4) 0.0499(16) Uani 1 1 d . . . . .
O9 O 0.3172(4) 0.3566(6) 0.6091(4) 0.0497(16) Uani 1 1 d . . . . .
O10 O 0.3574(4) 0.2513(6) 0.5223(4) 0.0499(16) Uani 1 1 d . . . . .
S3 S 0.89193(13) 0.7571(2) 0.84216(14) 0.0419(5) Uani 0.5 1 d . . P A 1
P3 P 0.89193(13) 0.7571(2) 0.84216(14) 0.0419(5) Uani 0.5 1 d . . P A 2
O11 O 0.8875(4) 0.6399(6) 0.8046(4) 0.0562(18) Uani 1 1 d . . . . .
O12 O 0.8485(5) 0.7577(10) 0.8897(5) 0.089(3) Uani 1 1 d . . . . .
O13 O 0.8673(4) 0.8560(6) 0.7835(4) 0.0520(17) Uani 1 1 d . . . . .
C7 C 0.9896(5) 0.7809(8) 0.9139(5) 0.0413(19) Uani 1 1 d . . . . .
H7B H 1.0091 0.7131 0.9517 0.050 Uiso 1 1 calc R U . A 1
H7A H 1.0197 0.7874 0.8848 0.050 Uiso 1 1 calc R U . A 1
C8 C 0.9981(5) 0.8930(8) 0.9620(5) 0.0382(18) Uani 1 1 d . . . . .
C9 C 0.9948(7) 1.0000 0.9242(7) 0.038(3) Uani 1 2 d S T P . .
H9 H 0.9902 1.0000 0.8712 0.046 Uiso 1 2 calc R U 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
La1 O6 2.429(6) . ?
La1 O6 2.429(6) 6_565 ?
La1 O11 2.475(7) . ?
La1 O11 2.475(7) 6_565 ?
La1 O8 2.484(6) 8 ?
La1 O8 2.484(6) 3 ?
La1 O1 2.617(9) . ?
La1 O4 2.683(13) . ?
La2 O5 2.387(6) 6 ?
La2 O5 2.387(6) . ?
La2 O13 2.467(7) 6_565 ?
La2 O13 2.467(6) 1_545 ?
La2 O9 2.485(7) 3_545 ?
La2 O9 2.485(7) 8 ?
La2 O2 2.655(9) . ?
La2 O3 2.673(15) . ?
S1 O6 1.464(6) . ?
S1 O5 1.490(7) . ?
S1 O7 1.510(7) . ?
S1 C1 1.781(8) . ?
P1 O6 1.464(6) . ?
P1 O5 1.490(7) . ?
P1 O7 1.510(7) . ?
P1 C1 1.781(8) . ?
C1 C2 1.495(11) . ?
C2 C3 1.394(9) . ?
C2 C5 1.394(10) . ?
C3 C2 1.394(9) 6_565 ?
C4 C5 1.403(9) . ?
C4 C5 1.403(9) 6_565 ?
C5 C6 1.501(11) . ?
C6 P2 1.798(9) . ?
C6 S2 1.798(9) . ?
S2 O8 1.477(7) . ?
S2 O9 1.477(7) . ?
S2 O10 1.514(7) . ?
P2 O8 1.477(7) . ?
P2 O9 1.477(7) . ?
P2 O10 1.514(7) . ?
O8 La1 2.484(6) 3_445 ?
O9 La2 2.485(7) 3_455 ?
S3 O13 1.480(7) . ?
S3 O11 1.487(7) . ?
S3 O12 1.512(8) . ?
S3 C7 1.787(9) . ?
P3 O13 1.480(7) . ?
P3 O11 1.487(7) . ?
P3 O12 1.512(8) . ?
P3 C7 1.787(9) . ?
O13 La2 2.467(6) 1_565 ?
C7 C8 1.520(12) . ?
C8 C8 1.384(17) 2_757 ?
C8 C9 1.391(10) . ?
C9 C8 1.391(10) 6_575 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 La1 O6 88.1(3) . 6_565 ?
O6 La1 O11 138.2(3) . . ?
O6 La1 O11 81.5(2) 6_565 . ?
O6 La1 O11 81.5(2) . 6_565 ?
O6 La1 O11 138.2(3) 6_565 6_565 ?
O11 La1 O11 79.9(3) . 6_565 ?
O6 La1 O8 85.5(2) . 8 ?
O6 La1 O8 144.6(2) 6_565 8 ?
O11 La1 O8 124.5(2) . 8 ?
O11 La1 O8 75.0(2) 6_565 8 ?
O6 La1 O8 144.6(2) . 3 ?
O6 La1 O8 85.5(2) 6_565 3 ?
O11 La1 O8 75.0(2) . 3 ?
O11 La1 O8 124.5(2) 6_565 3 ?
O8 La1 O8 80.0(3) 8 3 ?
O6 La1 O1 74.0(2) . . ?
O6 La1 O1 74.0(2) 6_565 . ?
O11 La1 O1 138.95(17) . . ?
O11 La1 O1 138.95(17) 6_565 . ?
O8 La1 O1 70.8(2) 8 . ?
O8 La1 O1 70.8(2) 3 . ?
O6 La1 O4 70.1(3) . . ?
O6 La1 O4 70.1(3) 6_565 . ?
O11 La1 O4 68.2(3) . . ?
O11 La1 O4 68.2(3) 6_565 . ?
O8 La1 O4 138.07(19) 8 . ?
O8 La1 O4 138.07(19) 3 . ?
O1 La1 O4 129.2(4) . . ?
O5 La2 O5 82.5(3) 6 . ?
O5 La2 O13 143.9(3) 6 6_565 ?
O5 La2 O13 86.2(2) . 6_565 ?
O5 La2 O13 86.2(2) 6 1_545 ?
O5 La2 O13 143.9(3) . 1_545 ?
O13 La2 O13 83.0(3) 6_565 1_545 ?
O5 La2 O9 84.3(2) 6 3_545 ?
O5 La2 O9 139.9(2) . 3_545 ?
O13 La2 O9 124.2(2) 6_565 3_545 ?
O13 La2 O9 72.1(2) 1_545 3_545 ?
O5 La2 O9 139.9(2) 6 8 ?
O5 La2 O9 84.3(2) . 8 ?
O13 La2 O9 72.1(2) 6_565 8 ?
O13 La2 O9 124.2(2) 1_545 8 ?
O9 La2 O9 81.9(3) 3_545 8 ?
O5 La2 O2 70.6(2) 6 . ?
O5 La2 O2 70.6(2) . . ?
O13 La2 O2 136.34(18) 6_565 . ?
O13 La2 O2 136.34(18) 1_545 . ?
O9 La2 O2 69.3(2) 3_545 . ?
O9 La2 O2 69.3(2) 8 . ?
O5 La2 O3 73.3(3) 6 . ?
O5 La2 O3 73.3(3) . . ?
O13 La2 O3 70.6(3) 6_565 . ?
O13 La2 O3 70.6(3) 1_545 . ?
O9 La2 O3 137.31(19) 3_545 . ?
O9 La2 O3 137.31(19) 8 . ?
O2 La2 O3 131.2(4) . . ?
O6 S1 O5 113.7(4) . . ?
O6 S1 O7 111.5(5) . . ?
O5 S1 O7 109.1(5) . . ?
O6 S1 C1 109.3(4) . . ?
O5 S1 C1 106.5(4) . . ?
O7 S1 C1 106.5(4) . . ?
O6 P1 O5 113.7(4) . . ?
O6 P1 O7 111.5(5) . . ?
O5 P1 O7 109.1(5) . . ?
O6 P1 C1 109.3(4) . . ?
O5 P1 C1 106.5(4) . . ?
O7 P1 C1 106.5(4) . . ?
P1 O5 La2 148.6(4) . . ?
S1 O5 La2 148.6(4) . . ?
P1 O6 La1 174.2(4) . . ?
S1 O6 La1 174.2(4) . . ?
C2 C1 S1 111.3(6) . . ?
C2 C1 P1 111.3(6) . . ?
C3 C2 C5 118.0(8) . . ?
C3 C2 C1 118.4(7) . . ?
C5 C2 C1 123.4(7) . . ?
C2 C3 C2 123.6(10) . 6_565 ?
C5 C4 C5 121.6(10) . 6_565 ?
C2 C5 C4 119.3(8) . . ?
C2 C5 C6 122.7(7) . . ?
C4 C5 C6 117.9(7) . . ?
C5 C6 P2 112.3(6) . . ?
C5 C6 S2 112.3(6) . . ?
O8 S2 O9 114.6(4) . . ?
O8 S2 O10 110.3(4) . . ?
O9 S2 O10 109.3(4) . . ?
O8 S2 C6 108.4(4) . . ?
O9 S2 C6 108.3(4) . . ?
O10 S2 C6 105.4(4) . . ?
O8 P2 O9 114.6(4) . . ?
O8 P2 O10 110.3(4) . . ?
O9 P2 O10 109.3(4) . . ?
O8 P2 C6 108.4(4) . . ?
O9 P2 C6 108.3(4) . . ?
O10 P2 C6 105.4(4) . . ?
P2 O8 La1 156.7(4) . 3_445 ?
S2 O8 La1 156.7(4) . 3_445 ?
P2 O9 La2 152.5(4) . 3_455 ?
S2 O9 La2 152.5(4) . 3_455 ?
O13 S3 O11 114.0(4) . . ?
O13 S3 O12 110.4(6) . . ?
O11 S3 O12 111.1(5) . . ?
O13 S3 C7 107.4(4) . . ?
O11 S3 C7 106.6(4) . . ?
O12 S3 C7 106.9(5) . . ?
O13 P3 O11 114.0(4) . . ?
O13 P3 O12 110.4(6) . . ?
O11 P3 O12 111.1(5) . . ?
O13 P3 C7 107.4(4) . . ?
O11 P3 C7 106.6(4) . . ?
O12 P3 C7 106.9(5) . . ?
P3 O11 La1 143.9(4) . . ?
S3 O11 La1 143.9(4) . . ?
P3 O13 La2 157.9(4) . 1_565 ?
S3 O13 La2 157.9(4) . 1_565 ?
C8 C7 S3 110.1(6) . . ?
C8 C7 P3 110.1(6) . . ?
C8 C8 C9 119.1(6) 2_757 . ?
C8 C8 C7 122.8(5) 2_757 . ?
C9 C8 C7 117.8(8) . . ?
C8 C9 C8 121.7(11) 6_575 . ?

_refine_diff_density_max         1.523
_refine_diff_density_min         -1.914
_refine_diff_density_rms         0.181



