# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_dh2_056
_database_code_depnum_ccdc_archive 'CCDC 986673'
_audit_update_record             
;
2014-02-13 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H22 O3 P2'
_chemical_formula_sum            'C21 H22 O3 P2'
_chemical_properties_physical    
'air-sensitive, moisture-sensitive, photo-sensitive'
_exptl_crystal_recrystallization_method THF
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      120(2)
_chemical_formula_weight         384.33

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1039(5)
_cell_length_b                   8.2133(6)
_cell_length_c                   17.3480(12)
_cell_angle_alpha                102.227(6)
_cell_angle_beta                 90.177(6)
_cell_angle_gamma                90.407(6)
_cell_volume                     989.20(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19150
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         29.02
_reflns_number_total             4744
_reflns_number_gt                4256
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0883P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4744
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1280
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.079
_refine_ls_shift/su_mean         0.004

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P2 P 0.96141(9) 0.40399(8) 0.18419(4) 0.02721(16) Uani 1 1 d . . .
P1 P 0.58752(9) 0.51812(9) 0.25443(4) 0.03141(17) Uani 1 1 d . . .
O2 O 0.9326(2) 0.57874(19) 0.33282(9) 0.0248(3) Uani 1 1 d . . .
O1 O 0.5932(3) 0.4062(2) 0.16037(10) 0.0301(4) Uani 1 1 d . . .
O3 O 0.6629(3) 0.6709(2) 0.39226(10) 0.0338(4) Uani 1 1 d . . .
C6 C 0.7409(3) 0.0003(3) -0.05095(12) 0.0239(4) Uani 1 1 d . . .
H6 H 0.7388 -0.1156 -0.0628 0.029 Uiso 1 1 calc R . .
C3 C 0.7515(3) 0.2596(3) 0.04491(12) 0.0219(4) Uani 1 1 d . . .
C9 C 0.7357(3) 0.2606(3) -0.09391(13) 0.0243(5) Uani 1 1 d . . .
H9 H 0.7310 0.3186 -0.1344 0.029 Uiso 1 1 calc R . .
C2 C 0.7608(3) 0.3543(3) 0.12871(12) 0.0229(4) Uani 1 1 d . . .
C10 C 0.7435(3) 0.3491(3) -0.01611(13) 0.0232(4) Uani 1 1 d . . .
C4 C 0.7502(3) 0.0843(3) 0.02780(13) 0.0230(4) Uani 1 1 d . . .
C13 C 0.9557(3) 0.7258(2) 0.46587(12) 0.0219(4) Uani 1 1 d . . .
C12 C 0.8335(3) 0.6596(3) 0.39624(13) 0.0247(5) Uani 1 1 d . . .
C1 C 0.8272(3) 0.5107(3) 0.26557(13) 0.0236(5) Uani 1 1 d . . .
C7 C 0.7346(3) 0.0864(3) -0.11254(13) 0.0237(4) Uani 1 1 d . . .
C18 C 1.2939(4) 0.9236(3) 0.67240(14) 0.0369(6) Uani 1 1 d . . .
H18A H 1.3825 0.8417 0.6812 0.055 Uiso 1 1 calc R . .
H18B H 1.2138 0.9538 0.7176 0.055 Uiso 1 1 calc R . .
H18C H 1.3604 1.0206 0.6642 0.055 Uiso 1 1 calc R . .
C8 C 0.7274(4) -0.0071(3) -0.19743(13) 0.0320(5) Uani 1 1 d . . .
H8A H 0.8531 -0.0288 -0.2168 0.048 Uiso 1 1 calc R . .
H8B H 0.6631 0.0587 -0.2287 0.048 Uiso 1 1 calc R . .
H8C H 0.6612 -0.1107 -0.2008 0.048 Uiso 1 1 calc R . .
C16 C 1.2330(4) 0.8723(3) 0.52581(13) 0.0262(5) Uani 1 1 d . . .
H16 H 1.3447 0.9294 0.5215 0.031 Uiso 1 1 calc R . .
C17 C 1.1752(4) 0.8523(3) 0.60025(14) 0.0267(5) Uani 1 1 d . . .
C11 C 0.7429(4) 0.5376(2) 0.00204(14) 0.0280(5) Uani 1 1 d . . .
H11A H 0.6460 0.5771 0.0397 0.042 Uiso 1 1 calc R . .
H11B H 0.7194 0.5763 -0.0456 0.042 Uiso 1 1 calc R . .
H11C H 0.8629 0.5789 0.0235 0.042 Uiso 1 1 calc R . .
C5 C 0.7547(4) -0.0148(3) 0.09231(13) 0.0288(5) Uani 1 1 d . . .
H5A H 0.6776 -0.1129 0.0770 0.043 Uiso 1 1 calc R . .
H5B H 0.7075 0.0523 0.1404 0.043 Uiso 1 1 calc R . .
H5C H 0.8819 -0.0466 0.1004 0.043 Uiso 1 1 calc R . .
C14 C 1.1278(3) 0.8089(3) 0.45782(13) 0.0244(5) Uani 1 1 d . . .
C15 C 1.2016(4) 0.8360(3) 0.38006(13) 0.0296(5) Uani 1 1 d . . .
H15A H 1.2595 0.7357 0.3519 0.044 Uiso 1 1 calc R . .
H15B H 1.2929 0.9249 0.3894 0.044 Uiso 1 1 calc R . .
H15C H 1.0993 0.8648 0.3493 0.044 Uiso 1 1 calc R . .
C19 C 1.0070(4) 0.7683(3) 0.60591(13) 0.0262(5) Uani 1 1 d . . .
H19 H 0.9691 0.7532 0.6552 0.031 Uiso 1 1 calc R . .
C20 C 0.8929(3) 0.7056(3) 0.54079(13) 0.0230(4) Uani 1 1 d . . .
C21 C 0.7101(4) 0.6167(3) 0.55184(14) 0.0296(5) Uani 1 1 d . . .
H21A H 0.6056 0.6847 0.5438 0.044 Uiso 1 1 calc R . .
H21B H 0.7056 0.5967 0.6044 0.044 Uiso 1 1 calc R . .
H21C H 0.7035 0.5124 0.5144 0.044 Uiso 1 1 calc R . .


_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
P2 C2 1.715(2) . ?
P2 C1 1.780(2) . ?
P1 O1 1.6955(17) . ?
P1 C1 1.716(3) . ?
O2 C12 1.360(3) . ?
O2 C1 1.395(3) . ?
O1 C2 1.346(3) . ?
O3 C12 1.219(3) . ?
C6 C4 1.395(3) . ?
C6 C7 1.402(3) . ?
C6 H6 0.9300 . ?
C3 C4 1.407(3) . ?
C3 C10 1.412(3) . ?
C3 C2 1.497(3) . ?
C9 C10 1.392(3) . ?
C9 C7 1.398(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.513(3) . ?
C4 C5 1.517(3) . ?
C13 C14 1.418(3) . ?
C13 C20 1.418(3) . ?
C13 C12 1.489(3) . ?
C7 C8 1.510(3) . ?
C18 C17 1.515(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C16 C14 1.396(3) . ?
C16 C17 1.398(3) . ?
C16 H16 0.9300 . ?
C17 C19 1.390(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C14 C15 1.508(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C19 C20 1.393(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.518(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 P2 C1 90.90(11) . . ?
O1 P1 C1 93.04(10) . . ?
C12 O2 C1 116.00(19) . . ?
C2 O1 P1 118.70(15) . . ?
C4 C6 C7 121.53(19) . . ?
C4 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C4 C3 C10 120.92(19) . . ?
C4 C3 C2 120.16(19) . . ?
C10 C3 C2 118.92(18) . . ?
C10 C9 C7 121.5(2) . . ?
C10 C9 H9 119.2 . . ?
C7 C9 H9 119.2 . . ?
O1 C2 C3 114.7(2) . . ?
O1 C2 P2 119.24(15) . . ?
C3 C2 P2 126.07(18) . . ?
C9 C10 C3 118.70(19) . . ?
C9 C10 C11 120.20(19) . . ?
C3 C10 C11 121.10(19) . . ?
C6 C4 C3 118.6(2) . . ?
C6 C4 C5 119.46(19) . . ?
C3 C4 C5 121.95(19) . . ?
C14 C13 C20 121.0(2) . . ?
C14 C13 C12 121.1(2) . . ?
C20 C13 C12 117.9(2) . . ?
O3 C12 O2 120.3(2) . . ?
O3 C12 C13 127.0(2) . . ?
O2 C12 C13 112.7(2) . . ?
O2 C1 P1 127.16(17) . . ?
O2 C1 P2 114.71(17) . . ?
P1 C1 P2 118.13(13) . . ?
C9 C7 C6 118.73(19) . . ?
C9 C7 C8 120.6(2) . . ?
C6 C7 C8 120.6(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C16 C17 121.8(2) . . ?
C14 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C19 C17 C16 118.4(2) . . ?
C19 C17 C18 121.6(2) . . ?
C16 C17 C18 120.0(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C16 C14 C13 118.3(2) . . ?
C16 C14 C15 118.1(2) . . ?
C13 C14 C15 123.6(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C19 C20 122.7(2) . . ?
C17 C19 H19 118.6 . . ?
C20 C19 H19 118.6 . . ?
C19 C20 C13 117.8(2) . . ?
C19 C20 C21 119.6(2) . . ?
C13 C20 C21 122.6(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.900
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_publishable_micha9_test9
_database_code_depnum_ccdc_archive 'CCDC 1454789'
_audit_update_record             
;
2016-02-19 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT201_publishable_micha9_test9 
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         12 Report
RESPONSE: Due to the high disorder of the coordinating DME molecules it was not possible to solve the H atoms isotropically.
;

# Added during the CSD deposition process: Friday 19th of February 2016 02:50:21 PM
# end Validation Reply Form

_audit_creation_date             2014-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_chemical_name_common            124-thiodiphospholide
_chemical_name_systematic        
sodium(1-thio-2,4-diphosphol-5-mesitoyl-3-olate)
_chemical_formula_moiety         'C38 H62 Na2 O10 P4 S2'
_chemical_formula_sum            'C38 H62 Na2 O10 P4 S2'
_chemical_formula_weight         912.86
_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'
Na Na 0.0362 0.0249 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4422(4)
_cell_length_b                   10.6570(4)
_cell_length_c                   24.5794(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.2517(7)
_cell_angle_gamma                90.00
_cell_volume                     2433.83(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6600
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.141
_cell_measurement_theta_min      2.204
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.8880
_exptl_absorpt_correction_T_min  0.8123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0465 before and 0.0347 after correction.
The Ratio of minimum to maximum transmission is 0.9148.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            18542
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.68
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'fixed chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker equipped with an APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_number_gt                4123
_reflns_number_total             4974
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    OLEX2
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4974
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0537P)²+2.8604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1310
_refine_special_details          
'Each of the dimethoxy ethane molecules are disordered over three positions and were described by partially occupied positions constrained to a total occupancy of one. The corresponding atoms were refined with isotropic displacement parameters.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Same fragment restrains
{C12A, O2A, C13A, C14A, O3A, C15A}
as
{C16, O4, C17, C18, O5, C19}
{C16A, O4A, C17A, C18A, O5A, C19A}
as
{C12, O2, C13, C14, O3, C15}
{C20, O6, C21, C22, O7, C23}
as
{C12A, O2A, C13A, C14A, O3A, C15A}
{C24, O8, C25, C26, O9, C27}
as
{C16A, O4A, C17A, C18A, O5A, C19A}
3. Others
 1*[Sof(C16)+Sof(H16A)+Sof(H16B)+Sof(H16C)+Sof(O4)+Sof(C17)+Sof(H17A)+
 Sof(H17B)+Sof(C18)+Sof(H18A)+Sof(H18B)+Sof(O5)+Sof(C19)+Sof(H19A)+Sof(H19B)+
 Sof(H19C)+Sof(C12)+Sof(H12A)+Sof(H12B)+Sof(H12C)+Sof(O2)+Sof(C13)+Sof(H13A)+
 Sof(H13B)+Sof(C14)+Sof(H14B)+Sof(H14A)+Sof(O3)+Sof(C15)+Sof(H15A)+Sof(H15B)+
 Sof(H15C)]+1*[Sof(C12A)+Sof(H12D)+Sof(H12E)+Sof(H12F)+Sof(O2A)+Sof(C13A)+
 Sof(H13C)+Sof(H13D)+Sof(C14A)+Sof(H14C)+Sof(H14D)+Sof(O3A)+Sof(C15A)+Sof(H15D)+
 Sof(H15E)+Sof(H15F)+Sof(C16A)+Sof(H16D)+Sof(H16E)+Sof(H16F)+Sof(O4A)+Sof(C17A)+
 Sof(H17C)+Sof(H17D)+Sof(C18A)+Sof(H18C)+Sof(H18D)+Sof(O5A)+Sof(C19A)+Sof(H19D)+
 Sof(H19E)+Sof(H19F)]+1*[Sof(C20)+Sof(H20A)+Sof(H20B)+Sof(H20C)+Sof(O6)+
 Sof(C21)+Sof(H21A)+Sof(H21B)+Sof(C22)+Sof(H22A)+Sof(H22B)+Sof(O7)+Sof(C23)+
 Sof(H23A)+Sof(H23B)+Sof(H23C)+Sof(C24)+Sof(H24A)+Sof(H24B)+Sof(H24C)+Sof(O8)+
 Sof(C25)+Sof(H25A)+Sof(H25B)+Sof(C26)+Sof(H26A)+Sof(H26B)+Sof(O9)+Sof(C27)+
 Sof(H27A)+Sof(H27B)+Sof(H27C)]=1 with esd of 0.0001
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(O4)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(O5)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(O2)=Sof(C13)=Sof(H13A)=Sof(H13B)=
 Sof(C14)=Sof(H14B)=Sof(H14A)=Sof(O3)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=
 FVAR(1)
 Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=Sof(O2A)=Sof(C13A)=Sof(H13C)=
 Sof(H13D)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(O3A)=Sof(C15A)=Sof(H15D)=Sof(H15E)=
 Sof(H15F)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(O4A)=Sof(C17A)=Sof(H17C)=
 Sof(H17D)=Sof(C18A)=Sof(H18C)=Sof(H18D)=Sof(O5A)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=FVAR(2)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(O6)=Sof(C21)=Sof(H21A)=Sof(H21B)=
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(O7)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(O8)=Sof(C25)=Sof(H25A)=Sof(H25B)=
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(O9)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=
 FVAR(3)
 Uiso(O4)=Uiso(O5)=Uiso(O2)=Uiso(O3)=Uiso(O2A)=Uiso(O3A)=Uiso(O4A)=Uiso(O5A)=
 Uiso(O6)=Uiso(O7)=Uiso(O8)=Uiso(O9)=FVAR(4)
 Uiso(C16)=Uiso(C19)=Uiso(C12)=Uiso(C15)=Uiso(C12A)=Uiso(C15A)=Uiso(C16A)=
 Uiso(C19A)=Uiso(C20)=Uiso(C23)=Uiso(C24)=Uiso(C27)=FVAR(5)
 Uiso(C17)=Uiso(C18)=Uiso(C13)=Uiso(C14)=Uiso(C13A)=Uiso(C14A)=Uiso(C17A)=
 Uiso(C18A)=Uiso(C21)=Uiso(C22)=Uiso(C25)=Uiso(C26)=FVAR(6)
4.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C13(H13A,H13B), C14(H14B,H14A), C13A(H13C,
 H13D), C14A(H14C,H14D), C17A(H17C,H17D), C18A(H18C,H18D), C21(H21A,H21B),
 C22(H22A,H22B), C25(H25A,H25B), C26(H26A,H26B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C16(H16A,H16B,
 H16C), C19(H19A,H19B,H19C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C),
 C12A(H12D,H12E,H12F), C15A(H15D,H15E,H15F), C16A(H16D,H16E,H16F), C19A(H19D,
 H19E,H19F), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C),
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
P1 P 0.29855(7) 0.38053(6) 0.10251(3) 0.03104(17) Uani 1 d A . .
S1 S 0.24454(7) 0.15469(6) 0.16706(3) 0.03515(17) Uani 1 d . . .
P2 P 0.05431(7) 0.19425(7) 0.11234(3) 0.03508(18) Uani 1 d A . .
Na4 Na -0.04232(10) 0.59631(9) 0.04971(4) 0.0300(2) Uani 1 d . . .
O1 O 0.03181(18) 0.38906(17) 0.04279(7) 0.0330(4) Uani 1 d . . .
C1 C 0.3568(3) 0.2714(2) 0.15192(10) 0.0276(5) Uani 1 d . . .
C2 C 0.1144(3) 0.3289(2) 0.08067(9) 0.0277(5) Uani 1 d . . .
C3 C 0.5049(3) 0.2716(2) 0.18517(10) 0.0284(5) Uani 1 d . . .
C4 C 0.5394(3) 0.3534(2) 0.23031(11) 0.0342(6) Uani 1 d . . .
C5 C 0.6790(3) 0.3532(3) 0.26051(12) 0.0400(6) Uani 1 d . . .
H5 H 0.7017 0.4073 0.2915 0.048 Uiso 1 calc . . R
C6 C 0.7853(3) 0.2770(3) 0.24681(12) 0.0394(6) Uani 1 d . . .
C7 C 0.7492(3) 0.1972(3) 0.20190(11) 0.0382(6) Uani 1 d . . .
H7 H 0.8215 0.1442 0.1920 0.046 Uiso 1 calc . . R
C8 C 0.6114(3) 0.1922(2) 0.17108(10) 0.0327(5) Uani 1 d . . .
C9 C 0.4282(3) 0.4424(3) 0.24584(13) 0.0490(8) Uani 1 d . . .
H9A H 0.4101 0.5102 0.2185 0.073 Uiso 1 calc . . GR
H9B H 0.4640 0.4780 0.2825 0.073 Uiso 1 calc . . GR
H9C H 0.3385 0.3967 0.2466 0.073 Uiso 1 calc . . GR
C10 C 0.5796(4) 0.1050(3) 0.12202(12) 0.0479(7) Uani 1 d . . .
H10A H 0.5110 0.0406 0.1291 0.072 Uiso 1 calc . . GR
H10B H 0.6689 0.0648 0.1161 0.072 Uiso 1 calc . . GR
H10C H 0.5380 0.1531 0.0890 0.072 Uiso 1 calc . . GR
C11 C 0.9365(3) 0.2800(3) 0.27931(14) 0.0547(8) Uani 1 d . . .
H11A H 0.9524 0.3594 0.2996 0.082 Uiso 1 calc . . GR
H11B H 1.0052 0.2727 0.2539 0.082 Uiso 1 calc . . GR
H11C H 0.9501 0.2099 0.3055 0.082 Uiso 1 calc . . GR
C16 C -0.2946(6) 0.4129(5) 0.0877(3) 0.0439(6) Uiso 0.565(2) d A 1 .
H16A H -0.2219 0.3535 0.0796 0.066 Uiso 0.565(2) calc A 1 GR
H16B H -0.3903 0.3846 0.0698 0.066 Uiso 0.565(2) calc A 1 GR
H16C H -0.2906 0.4174 0.1277 0.066 Uiso 0.565(2) calc A 1 GR
O4 O -0.2675(5) 0.5310(4) 0.06775(16) 0.0341(4) Uiso 0.565(2) d A 1 .
C17 C -0.3593(6) 0.6233(5) 0.0814(2) 0.0451(6) Uiso 0.565(2) d A 1 .
H17A H -0.3443 0.6319 0.1221 0.054 Uiso 0.565(2) calc A 1 R
H17B H -0.4602 0.5967 0.0685 0.054 Uiso 0.565(2) calc A 1 R
C18 C -0.3370(6) 0.7434(6) 0.0575(2) 0.0451(6) Uiso 0.565(2) d A 1 .
H18A H -0.3764 0.7403 0.0174 0.054 Uiso 0.565(2) calc A 1 R
H18B H -0.3921 0.8076 0.0741 0.054 Uiso 0.565(2) calc A 1 R
O5 O -0.1967(4) 0.7801(3) 0.06446(16) 0.0341(4) Uiso 0.565(2) d A 1 .
C19 C -0.1695(7) 0.8926(6) 0.0387(2) 0.0439(6) Uiso 0.565(2) d A 1 .
H19A H -0.1715 0.8774 -0.0007 0.066 Uiso 0.565(2) calc A 1 GR
H19B H -0.0746 0.9246 0.0557 0.066 Uiso 0.565(2) calc A 1 GR
H19C H -0.2434 0.9544 0.0432 0.066 Uiso 0.565(2) calc A 1 GR
C12 C 0.2297(6) 0.7923(6) 0.0356(2) 0.0439(6) Uiso 0.565(2) d A 1 .
H12A H 0.3027 0.7307 0.0299 0.066 Uiso 0.565(2) calc A 1 GR
H12B H 0.2769 0.8703 0.0501 0.066 Uiso 0.565(2) calc A 1 GR
H12C H 0.1660 0.8093 0.0004 0.066 Uiso 0.565(2) calc A 1 GR
O2 O 0.1520(5) 0.7465(5) 0.07194(18) 0.0341(4) Uiso 0.565(2) d A 1 .
C13 C 0.2172(7) 0.7547(6) 0.1300(2) 0.0451(6) Uiso 0.565(2) d A 1 .
H13A H 0.3124 0.7130 0.1355 0.054 Uiso 0.565(2) calc A 1 R
H13B H 0.2332 0.8442 0.1400 0.054 Uiso 0.565(2) calc A 1 R
C14 C 0.1340(7) 0.6997(6) 0.1656(3) 0.0451(6) Uiso 0.565(2) d A 1 .
H14B H 0.1967 0.6863 0.2019 0.054 Uiso 0.565(2) calc A 1 R
H14A H 0.0586 0.7604 0.1713 0.054 Uiso 0.565(2) calc A 1 R
O3 O 0.0695(4) 0.5902(3) 0.14914(13) 0.0341(4) Uiso 0.565(2) d A 1 .
C15 C 0.0001(6) 0.5334(6) 0.1889(3) 0.0439(6) Uiso 0.565(2) d A 1 .
H15A H -0.0825 0.5847 0.1943 0.066 Uiso 0.565(2) calc A 1 GR
H15B H 0.0677 0.5264 0.2240 0.066 Uiso 0.565(2) calc A 1 GR
H15C H -0.0333 0.4495 0.1762 0.066 Uiso 0.565(2) calc A 1 GR
C12A C 0.1999(15) 0.8432(14) 0.0417(5) 0.0439(6) Uiso 0.223(3) d A 2 .
H12D H 0.1832 0.8085 0.0041 0.066 Uiso 0.223(3) calc A 2 GR
H12E H 0.3033 0.8425 0.0566 0.066 Uiso 0.223(3) calc A 2 GR
H12F H 0.1640 0.9295 0.0407 0.066 Uiso 0.223(3) calc A 2 GR
O2A O 0.1309(13) 0.7735(9) 0.0737(4) 0.0341(4) Uiso 0.223(3) d A 2 .
C13A C 0.1662(16) 0.7919(14) 0.1317(5) 0.0451(6) Uiso 0.223(3) d A 2 .
H13C H 0.2717 0.7819 0.1423 0.054 Uiso 0.223(3) calc A 2 R
H13D H 0.1441 0.8805 0.1390 0.054 Uiso 0.223(3) calc A 2 R
C14A C 0.1040(15) 0.7191(13) 0.1669(6) 0.0451(6) Uiso 0.223(3) d A 2 .
H14C H 0.1836 0.6767 0.1918 0.054 Uiso 0.223(3) calc A 2 R
H14D H 0.0590 0.7774 0.1902 0.054 Uiso 0.223(3) calc A 2 R
O3A O 0.0047(10) 0.6298(8) 0.1489(3) 0.0341(4) Uiso 0.223(3) d A 2 .
C15A C -0.0426(16) 0.5448(14) 0.1853(7) 0.0439(6) Uiso 0.223(3) d A 2 .
H15D H -0.1460 0.5299 0.1738 0.066 Uiso 0.223(3) calc A 2 GR
H15E H -0.0244 0.5798 0.2228 0.066 Uiso 0.223(3) calc A 2 GR
H15F H 0.0096 0.4654 0.1849 0.066 Uiso 0.223(3) calc A 2 GR
C16A C -0.3103(16) 0.3969(11) 0.0607(7) 0.0439(6) Uiso 0.223(3) d A 2 .
H16D H -0.2668 0.3474 0.0344 0.066 Uiso 0.223(3) calc A 2 GR
H16E H -0.4149 0.3847 0.0533 0.066 Uiso 0.223(3) calc A 2 GR
H16F H -0.2713 0.3694 0.0984 0.066 Uiso 0.223(3) calc A 2 GR
O4A O -0.2794(16) 0.5226(11) 0.0550(7) 0.0341(4) Uiso 0.223(3) d A 2 .
C17A C -0.3858(15) 0.6136(11) 0.0606(6) 0.0451(6) Uiso 0.223(3) d A 2 .
H17C H -0.3927 0.6216 0.1002 0.054 Uiso 0.223(3) calc A 2 R
H17D H -0.4802 0.5840 0.0406 0.054 Uiso 0.223(3) calc A 2 R
C18A C -0.3553(14) 0.7370(13) 0.0393(6) 0.0451(6) Uiso 0.223(3) d A 2 .
H18C H -0.4077 0.7423 0.0007 0.054 Uiso 0.223(3) calc A 2 R
H18D H -0.3984 0.8005 0.0608 0.054 Uiso 0.223(3) calc A 2 R
O5A O -0.2242(9) 0.7705(8) 0.0392(4) 0.0341(4) Uiso 0.223(3) d A 2 .
C19A C -0.2027(16) 0.8941(12) 0.0238(6) 0.0439(6) Uiso 0.223(3) d A 2 .
H19D H -0.2458 0.9061 -0.0151 0.066 Uiso 0.223(3) calc A 2 GR
H19E H -0.0993 0.9115 0.0290 0.066 Uiso 0.223(3) calc A 2 GR
H19F H -0.2480 0.9514 0.0468 0.066 Uiso 0.223(3) calc A 2 GR
C20 C 0.2510(14) 0.7394(15) 0.1159(6) 0.0439(6) Uiso 0.2116(19) d A 3 .
H20A H 0.2305 0.6988 0.1494 0.066 Uiso 0.2116(19) calc A 3 GR
H20B H 0.2902 0.8234 0.1251 0.066 Uiso 0.2116(19) calc A 3 GR
H20C H 0.3213 0.6892 0.1005 0.066 Uiso 0.2116(19) calc A 3 GR
O6 O 0.1290(13) 0.7486(13) 0.0785(5) 0.0341(4) Uiso 0.2116(19) d A 3 .
C21 C 0.0582(13) 0.8591(12) 0.0886(6) 0.0451(6) Uiso 0.2116(19) d A 3 .
H21A H 0.1282 0.9288 0.0909 0.054 Uiso 0.2116(19) calc A 3 R
H21B H 0.0300 0.8513 0.1254 0.054 Uiso 0.2116(19) calc A 3 R
C22 C -0.0675(13) 0.8942(12) 0.0497(6) 0.0451(6) Uiso 0.2116(19) d A 3 .
H22A H -0.1074 0.9733 0.0618 0.054 Uiso 0.2116(19) calc A 3 R
H22B H -0.0409 0.9089 0.0130 0.054 Uiso 0.2116(19) calc A 3 R
O7 O -0.1704(9) 0.8006(9) 0.0455(4) 0.0341(4) Uiso 0.2116(19) d A 3 .
C23 C -0.3020(13) 0.8386(13) 0.0109(6) 0.0439(6) Uiso 0.2116(19) d A 3 .
H23A H -0.2810 0.8717 -0.0240 0.066 Uiso 0.2116(19) calc A 3 GR
H23B H -0.3484 0.9038 0.0296 0.066 Uiso 0.2116(19) calc A 3 GR
H23C H -0.3664 0.7661 0.0033 0.066 Uiso 0.2116(19) calc A 3 GR
C24 C -0.3350(16) 0.4147(12) 0.0358(6) 0.0439(6) Uiso 0.2116(19) d A 3 .
H24A H -0.3118 0.3991 -0.0009 0.066 Uiso 0.2116(19) calc A 3 GR
H24B H -0.4386 0.4037 0.0344 0.066 Uiso 0.2116(19) calc A 3 GR
H24C H -0.2820 0.3554 0.0624 0.066 Uiso 0.2116(19) calc A 3 GR
O8 O -0.2955(14) 0.5382(10) 0.0523(6) 0.0341(4) Uiso 0.2116(19) d A 3 .
C25 C -0.3152(14) 0.5682(14) 0.1081(5) 0.0451(6) Uiso 0.2116(19) d A 3 .
H25A H -0.4047 0.5279 0.1150 0.054 Uiso 0.2116(19) calc A 3 R
H25B H -0.3271 0.6601 0.1111 0.054 Uiso 0.2116(19) calc A 3 R
C26 C -0.1952(12) 0.5275(13) 0.1506(5) 0.0451(6) Uiso 0.2116(19) d A 3 .
H26A H -0.2145 0.5503 0.1876 0.054 Uiso 0.2116(19) calc A 3 R
H26B H -0.1847 0.4352 0.1491 0.054 Uiso 0.2116(19) calc A 3 R
O9 O -0.0708(9) 0.5844(8) 0.1419(3) 0.0341(4) Uiso 0.2116(19) d A 3 .
C27 C 0.0467(14) 0.5592(15) 0.1857(6) 0.0439(6) Uiso 0.2116(19) d A 3 .
H27A H 0.0555 0.4684 0.1917 0.066 Uiso 0.2116(19) calc A 3 GR
H27B H 0.0294 0.6001 0.2196 0.066 Uiso 0.2116(19) calc A 3 GR
H27C H 0.1358 0.5918 0.1758 0.066 Uiso 0.2116(19) calc A 3 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
P1 C1 1.700(2) . ?
P1 C2 1.812(3) . ?
S1 P2 2.0864(9) . ?
S1 C1 1.718(2) . ?
P2 C2 1.773(2) . ?
Na4 O1 2.2986(19) 3_565 ?
Na4 O1 2.332(2) . ?
Na4 O4 2.353(5) . ?
Na4 O2 2.423(5) . ?
Na4 O3 2.485(3) . ?
Na4 O2A 2.500(11) . ?
Na4 O3A 2.425(8) . ?
Na4 O4A 2.397(15) . ?
Na4 O6 2.312(13) . ?
Na4 O7 2.484(9) . ?
Na4 O8 2.482(13) . ?
Na4 O9 2.332(8) . ?
O1 Na4 2.2986(19) 3_565 ?
O1 C2 1.276(3) . ?
C1 C3 1.489(3) . ?
C3 C4 1.403(4) . ?
C3 C8 1.405(3) . ?
C4 C5 1.393(4) . ?
C4 C9 1.513(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(4) . ?
C6 C7 1.387(4) . ?
C6 C11 1.508(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(4) . ?
C8 C10 1.509(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 O4 1.391(7) . ?
O4 C17 1.391(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.440(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 O5 1.363(7) . ?
O5 C19 1.400(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 O2 1.344(6) . ?
O2 C13 1.452(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.405(8) . ?
C14 H14B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 O3 1.345(7) . ?
O3 C15 1.407(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C12A O2A 1.334(13) . ?
O2A C13A 1.417(13) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C13A C14A 1.370(14) . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C14A O3A 1.354(14) . ?
O3A C15A 1.402(13) . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?
C16A O4A 1.384(13) . ?
O4A C17A 1.420(14) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C17A C18A 1.463(14) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C18A O5A 1.290(13) . ?
O5A C19A 1.394(13) . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 O6 1.343(14) . ?
O6 C21 1.397(14) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.436(14) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 O7 1.384(13) . ?
O7 C23 1.434(13) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 O8 1.408(13) . ?
O8 C25 1.451(15) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.463(14) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 O9 1.372(12) . ?
O9 C27 1.427(12) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C2 100.11(11) . . ?
C1 S1 P2 101.98(9) . . ?
C2 P2 S1 98.08(9) . . ?
O1 Na4 O1 85.74(7) 3_565 . ?
O1 Na4 O4 113.95(11) 3_565 . ?
O1 Na4 O4 91.53(13) . . ?
O1 Na4 O2 114.63(12) . . ?
O1 Na4 O2 90.80(12) 3_565 . ?
O1 Na4 O3 88.06(10) . . ?
O1 Na4 O3 152.75(10) 3_565 . ?
O1 Na4 O2A 122.7(3) . . ?
O1 Na4 O2A 92.3(3) 3_565 . ?
O1 Na4 O3A 102.1(2) . . ?
O1 Na4 O3A 162.1(2) 3_565 . ?
O1 Na4 O4A 89.4(3) . . ?
O1 Na4 O4A 106.3(4) 3_565 . ?
O1 Na4 O6 96.0(3) 3_565 . ?
O1 Na4 O7 167.8(2) . . ?
O1 Na4 O7 90.4(2) 3_565 . ?
O1 Na4 O8 104.7(4) 3_565 . ?
O1 Na4 O8 93.9(3) . . ?
O1 Na4 O9 175.9(2) 3_565 . ?
O4 Na4 O2 145.72(13) . . ?
O4 Na4 O3 92.69(13) . . ?
O4 Na4 O2A 139.0(3) . . ?
O4 Na4 O3A 82.2(2) . . ?
O4 Na4 O4A 7.8(4) . . ?
O4 Na4 O7 79.5(2) . . ?
O4 Na4 O8 9.7(3) . . ?
O2 Na4 O3 67.87(13) . . ?
O2 Na4 O2A 8.1(3) . . ?
O2 Na4 O3A 71.3(2) . . ?
O2 Na4 O7 76.9(2) . . ?
O2 Na4 O8 148.6(3) . . ?
O3 Na4 O2A 69.0(2) . . ?
O3A Na4 O3 17.3(2) . . ?
O3A Na4 O2A 69.9(3) . . ?
O3A Na4 O7 85.0(3) . . ?
O3A Na4 O8 90.9(4) . . ?
O4A Na4 O2 151.8(3) . . ?
O4A Na4 O3 100.1(4) . . ?
O4A Na4 O2A 144.4(4) . . ?
O4A Na4 O3A 90.0(4) . . ?
O4A Na4 O7 80.6(4) . . ?
O4A Na4 O8 5.0(5) . . ?
O6 Na4 O1 119.0(3) . . ?
O6 Na4 O4 139.1(3) . . ?
O6 Na4 O2 6.6(3) . . ?
O6 Na4 O3 64.2(3) . . ?
O6 Na4 O2A 5.4(5) . . ?
O6 Na4 O3A 66.1(4) . . ?
O6 Na4 O4A 145.3(4) . . ?
O6 Na4 O7 72.9(4) . . ?
O6 Na4 O8 142.4(4) . . ?
O6 Na4 O9 86.3(4) . . ?
O7 Na4 O3 100.5(2) . . ?
O7 Na4 O2A 69.0(3) . . ?
O8 Na4 O3 102.2(4) . . ?
O8 Na4 O2A 140.8(4) . . ?
O8 Na4 O7 75.8(3) . . ?
O9 Na4 O1 96.2(2) . . ?
O9 Na4 O4 62.4(2) . . ?
O9 Na4 O2 91.7(2) . . ?
O9 Na4 O3 31.3(2) . . ?
O9 Na4 O2A 89.7(3) . . ?
O9 Na4 O3A 20.5(2) . . ?
O9 Na4 O4A 70.1(4) . . ?
O9 Na4 O7 87.0(3) . . ?
O9 Na4 O8 71.5(4) . . ?
Na4 O1 Na4 94.26(7) 3_565 . ?
C2 O1 Na4 128.88(15) . 3_565 ?
C2 O1 Na4 125.09(16) . . ?
P1 C1 S1 121.08(15) . . ?
C3 C1 P1 122.96(17) . . ?
C3 C1 S1 115.95(17) . . ?
P2 C2 P1 118.74(13) . . ?
O1 C2 P1 119.57(18) . . ?
O1 C2 P2 121.69(19) . . ?
C4 C3 C1 119.9(2) . . ?
C4 C3 C8 119.6(2) . . ?
C8 C3 C1 120.5(2) . . ?
C3 C4 C9 121.0(2) . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 C9 120.0(2) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.1(3) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C7 118.0(3) . . ?
C5 C6 C11 121.3(3) . . ?
C7 C6 C11 120.6(3) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.2(2) . . ?
C8 C7 H7 118.9 . . ?
C3 C8 C10 121.2(2) . . ?
C7 C8 C3 119.1(2) . . ?
C7 C8 C10 119.7(2) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 O4 Na4 124.2(4) . . ?
C17 O4 Na4 117.3(3) . . ?
C17 O4 C16 113.2(4) . . ?
O4 C17 H17A 109.0 . . ?
O4 C17 H17B 109.0 . . ?
O4 C17 C18 112.8(5) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
O5 C18 C17 114.4(5) . . ?
O5 C18 H18A 108.7 . . ?
O5 C18 H18B 108.7 . . ?
C18 O5 Na4 109.6(3) . . ?
C18 O5 C19 116.2(4) . . ?
C19 O5 Na4 116.4(3) . . ?
C12 O2 Na4 124.8(4) . . ?
C12 O2 C13 116.4(5) . . ?
C13 O2 Na4 115.7(4) . . ?
O2 C13 H13A 108.8 . . ?
O2 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 O2 113.7(5) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C13 C14 H14B 108.1 . . ?
C13 C14 H14A 108.1 . . ?
H14B C14 H14A 107.3 . . ?
O3 C14 C13 116.6(5) . . ?
O3 C14 H14B 108.1 . . ?
O3 C14 H14A 108.1 . . ?
C14 O3 Na4 111.3(3) . . ?
C14 O3 C15 113.9(5) . . ?
C15 O3 Na4 121.7(3) . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
O2A C12A H12D 109.5 . . ?
O2A C12A H12E 109.5 . . ?
O2A C12A H12F 109.5 . . ?
C12A O2A Na4 130.4(9) . . ?
C12A O2A C13A 117.7(11) . . ?
C13A O2A Na4 111.6(7) . . ?
O2A C13A H13C 107.2 . . ?
O2A C13A H13D 107.2 . . ?
H13C C13A H13D 106.9 . . ?
C14A C13A O2A 120.4(12) . . ?
C14A C13A H13C 107.2 . . ?
C14A C13A H13D 107.2 . . ?
C13A C14A H14C 106.6 . . ?
C13A C14A H14D 106.6 . . ?
H14C C14A H14D 106.6 . . ?
O3A C14A C13A 122.7(13) . . ?
O3A C14A H14C 106.6 . . ?
O3A C14A H14D 106.6 . . ?
C14A O3A Na4 115.1(8) . . ?
C14A O3A C15A 121.7(11) . . ?
C15A O3A Na4 121.7(8) . . ?
O3A C15A H15D 109.5 . . ?
O3A C15A H15E 109.5 . . ?
O3A C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
O4A C16A H16D 109.5 . . ?
O4A C16A H16E 109.5 . . ?
O4A C16A H16F 109.5 . . ?
C16A O4A Na4 122.6(10) . . ?
C16A O4A C17A 119.0(12) . . ?
C17A O4A Na4 117.7(8) . . ?
O4A C17A H17C 109.0 . . ?
O4A C17A H17D 109.0 . . ?
O4A C17A C18A 113.0(11) . . ?
H17C C17A H17D 107.8 . . ?
C18A C17A H17C 109.0 . . ?
C18A C17A H17D 109.0 . . ?
C17A C18A H18C 107.3 . . ?
C17A C18A H18D 107.3 . . ?
H18C C18A H18D 106.9 . . ?
O5A C18A C17A 120.0(12) . . ?
O5A C18A H18C 107.3 . . ?
O5A C18A H18D 107.3 . . ?
C18A O5A Na4 115.7(8) . . ?
C18A O5A C19A 116.6(11) . . ?
C19A O5A Na4 126.6(8) . . ?
O5A C19A H19D 109.5 . . ?
O5A C19A H19E 109.5 . . ?
O5A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C20 O6 Na4 128.8(11) . . ?
C20 O6 C21 108.7(12) . . ?
C21 O6 Na4 108.3(8) . . ?
Na4 C21 H21A 150.9 . . ?
Na4 C21 H21B 95.2 . . ?
O6 C21 Na4 45.9(6) . . ?
O6 C21 H21A 107.9 . . ?
O6 C21 H21B 107.9 . . ?
O6 C21 C22 117.8(12) . . ?
H21A C21 H21B 107.2 . . ?
C22 C21 Na4 81.8(8) . . ?
C22 C21 H21A 107.9 . . ?
C22 C21 H21B 107.9 . . ?
C21 C22 H22A 109.6 . . ?
C21 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
O7 C22 C21 110.3(11) . . ?
O7 C22 H22A 109.6 . . ?
O7 C22 H22B 109.6 . . ?
C22 O7 Na4 107.4(7) . . ?
C22 O7 C23 111.3(10) . . ?
C23 O7 Na4 129.5(8) . . ?
C24 O8 Na4 115.6(9) . . ?
C24 O8 C25 114.0(12) . . ?
C25 O8 Na4 104.8(9) . . ?
O8 C25 H25A 108.9 . . ?
O8 C25 H25B 108.9 . . ?
O8 C25 C26 113.4(11) . . ?
H25A C25 H25B 107.7 . . ?
C26 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C25 C26 H26A 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.2 . . ?
O9 C26 C25 109.5(10) . . ?
O9 C26 H26A 109.8 . . ?
O9 C26 H26B 109.8 . . ?
C26 O9 Na4 115.2(7) . . ?
C26 O9 C27 111.8(10) . . ?
C27 O9 Na4 122.3(8) . . ?

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
P1 C1 C3 C4 79.7(3) . . . . ?
P1 C1 C3 C8 -99.1(3) . . . . ?
S1 P2 C2 P1 0.83(14) . . . . ?
S1 P2 C2 O1 -179.84(18) . . . . ?
S1 C1 C3 C4 -99.3(2) . . . . ?
S1 C1 C3 C8 81.9(3) . . . . ?
P2 S1 C1 P1 0.14(16) . . . . ?
P2 S1 C1 C3 179.11(16) . . . . ?
Na4 O1 C2 P1 68.8(3) 3_565 . . . ?
Na4 O1 C2 P1 -64.3(2) . . . . ?
Na4 O1 C2 P2 116.33(18) . . . . ?
Na4 O1 C2 P2 -110.58(19) 3_565 . . . ?
Na4 O4 C17 C18 28.4(6) . . . . ?
Na4 O2 C13 C14 -16.0(7) . . . . ?
Na4 O2A C13A C14A -1.8(18) . . . . ?
Na4 O4A C17A C18A 24.5(17) . . . . ?
Na4 O6 C21 C22 -42.6(14) . . . . ?
Na4 C21 C22 O7 29.4(10) . . . . ?
Na4 O8 C25 C26 -44.3(12) . . . . ?
O1 Na4 O1 Na4 0.0 3_565 . . 3_565 ?
O1 Na4 O1 C2 145.2(2) 3_565 . . . ?
O1 Na4 O4 C16 21.3(4) . . . . ?
O1 Na4 O4 C16 107.3(4) 3_565 . . . ?
O1 Na4 O4 C17 173.9(4) . . . . ?
O1 Na4 O4 C17 -100.1(4) 3_565 . . . ?
O1 Na4 O5 C18 92.1(3) 3_565 . . . ?
O1 Na4 O5 C18 -21.3(5) . . . . ?
O1 Na4 O5 C19 -42.3(3) 3_565 . . . ?
O1 Na4 O5 C19 -155.7(3) . . . . ?
O1 Na4 O2 C12 78.5(4) . . . . ?
O1 Na4 O2 C12 -7.2(4) 3_565 . . . ?
O1 Na4 O2 C13 -166.4(4) 3_565 . . . ?
O1 Na4 O2 C13 -80.7(4) . . . . ?
O1 Na4 O3 C14 64.9(4) 3_565 . . . ?
O1 Na4 O3 C14 141.7(3) . . . . ?
O1 Na4 O3 C15 -79.4(4) . . . . ?
O1 Na4 O3 C15 -156.3(4) 3_565 . . . ?
O1 Na4 O2A C12A 85.4(12) . . . . ?
O1 Na4 O2A C12A -1.1(12) 3_565 . . . ?
O1 Na4 O2A C13A -88.9(10) . . . . ?
O1 Na4 O2A C13A -175.3(9) 3_565 . . . ?
O1 Na4 O3A C14A 2.4(14) 3_565 . . . ?
O1 Na4 O3A C14A 116.9(9) . . . . ?
O1 Na4 O3A C15A -49.4(9) . . . . ?
O1 Na4 O3A C15A -164.0(8) 3_565 . . . ?
O1 Na4 O4A C16A 94.3(13) 3_565 . . . ?
O1 Na4 O4A C16A 8.9(13) . . . . ?
O1 Na4 O4A C17A -95.0(11) 3_565 . . . ?
O1 Na4 O4A C17A 179.6(12) . . . . ?
O1 Na4 O5A C18A 105.0(9) 3_565 . . . ?
O1 Na4 O5A C18A 25.2(13) . . . . ?
O1 Na4 O5A C19A -142.8(8) . . . . ?
O1 Na4 O5A C19A -63.0(10) 3_565 . . . ?
O1 Na4 O6 C20 -123.9(12) 3_565 . . . ?
O1 Na4 O6 C20 -35.5(14) . . . . ?
O1 Na4 O6 C21 -169.8(8) . . . . ?
O1 Na4 O6 C21 101.7(9) 3_565 . . . ?
O1 Na4 C21 O6 15.3(11) . . . . ?
O1 Na4 C21 O6 -82.0(9) 3_565 . . . ?
O1 Na4 C21 C22 60.8(8) 3_565 . . . ?
O1 Na4 C21 C22 158.0(6) . . . . ?
O1 Na4 O7 C22 -82.1(8) 3_565 . . . ?
O1 Na4 O7 C22 -153.3(9) . . . . ?
O1 Na4 O7 C23 56.5(10) 3_565 . . . ?
O1 Na4 O7 C23 -14.7(19) . . . . ?
O1 Na4 O8 C24 -15.1(11) . . . . ?
O1 Na4 O8 C24 71.6(11) 3_565 . . . ?
O1 Na4 O8 C25 111.3(8) . . . . ?
O1 Na4 O8 C25 -162.1(7) 3_565 . . . ?
O1 Na4 O9 C26 -78.7(8) . . . . ?
O1 Na4 O9 C26 38(4) 3_565 . . . ?
O1 Na4 O9 C27 180(100) 3_565 . . . ?
O1 Na4 O9 C27 62.8(10) . . . . ?
C1 P1 C2 P2 -0.78(17) . . . . ?
C1 P1 C2 O1 179.88(19) . . . . ?
C1 S1 P2 C2 -0.53(12) . . . . ?
C1 C3 C4 C5 -179.2(2) . . . . ?
C1 C3 C4 C9 -0.2(4) . . . . ?
C1 C3 C8 C7 178.2(2) . . . . ?
C1 C3 C8 C10 0.2(4) . . . . ?
C2 P1 C1 S1 0.32(17) . . . . ?
C2 P1 C1 C3 -178.6(2) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C4 C3 C8 C7 -0.6(4) . . . . ?
C4 C3 C8 C10 -178.6(2) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C4 C5 C6 C11 178.8(3) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C3 0.9(4) . . . . ?
C6 C7 C8 C10 178.9(3) . . . . ?
C8 C3 C4 C5 -0.4(4) . . . . ?
C8 C3 C4 C9 178.6(2) . . . . ?
C9 C4 C5 C6 -177.7(3) . . . . ?
C11 C6 C7 C8 -179.9(3) . . . . ?
C16 O4 C17 C18 -176.0(5) . . . . ?
O4 Na4 O1 Na4 113.91(11) . . . 3_565 ?
O4 Na4 O1 C2 -100.8(2) . . . . ?
O4 Na4 O5 C18 -19.0(3) . . . . ?
O4 Na4 O5 C19 -153.3(4) . . . . ?
O4 Na4 O2 C12 -145.0(4) . . . . ?
O4 Na4 O2 C13 55.7(5) . . . . ?
O4 Na4 O3 C14 -126.9(4) . . . . ?
O4 Na4 O3 C15 12.0(4) . . . . ?
O4 Na4 O2A C12A -132.8(11) . . . . ?
O4 Na4 O2A C13A 52.9(11) . . . . ?
O4 Na4 O3A C14A -153.1(9) . . . . ?
O4 Na4 O3A C15A 40.5(9) . . . . ?
O4 Na4 O4A C16A -97(4) . . . . ?
O4 Na4 O4A C17A 73(3) . . . . ?
O4 Na4 O5A C18A -11.2(9) . . . . ?
O4 Na4 O5A C19A -179.2(11) . . . . ?
O4 Na4 O6 C20 97.9(13) . . . . ?
O4 Na4 O6 C21 -36.5(11) . . . . ?
O4 Na4 C21 O6 154.1(8) . . . . ?
O4 Na4 C21 C22 -63.1(9) . . . . ?
O4 Na4 O7 C22 163.6(8) . . . . ?
O4 Na4 O7 C23 -57.8(10) . . . . ?
O4 Na4 O8 C24 -91.0(19) . . . . ?
O4 Na4 O8 C25 35.4(18) . . . . ?
O4 Na4 O9 C26 9.8(8) . . . . ?
O4 Na4 O9 C27 151.3(10) . . . . ?
O4 C17 C18 O5 -48.1(7) . . . . ?
C17 C18 O5 Na4 41.5(5) . . . . ?
C17 C18 O5 C19 176.0(5) . . . . ?
C12 O2 C13 C14 -177.0(5) . . . . ?
O2 Na4 O1 Na4 -88.93(13) . . . 3_565 ?
O2 Na4 O1 C2 56.3(2) . . . . ?
O2 Na4 O4 C16 -120.0(4) . . . . ?
O2 Na4 O4 C17 32.6(5) . . . . ?
O2 Na4 O5 C18 -178.5(3) . . . . ?
O2 Na4 O5 C19 47.1(3) . . . . ?
O2 Na4 O3 C14 24.1(3) . . . . ?
O2 Na4 O3 C15 162.9(4) . . . . ?
O2 Na4 O2A C12A 78(2) . . . . ?
O2 Na4 O2A C13A -96(2) . . . . ?
O2 Na4 O3A C14A 4.8(9) . . . . ?
O2 Na4 O3A C15A -161.6(10) . . . . ?
O2 Na4 O4A C16A -140.5(10) . . . . ?
O2 Na4 O4A C17A 30.2(18) . . . . ?
O2 Na4 O5A C18A -164.2(9) . . . . ?
O2 Na4 O5A C19A 27.8(10) . . . . ?
O2 Na4 O6 C20 -86(4) . . . . ?
O2 Na4 O6 C21 140(4) . . . . ?
O2 Na4 C21 O6 -8.2(8) . . . . ?
O2 Na4 C21 C22 134.5(11) . . . . ?
O2 Na4 O7 C22 8.7(8) . . . . ?
O2 Na4 O7 C23 147.3(10) . . . . ?
O2 Na4 O8 C24 -171.2(8) . . . . ?
O2 Na4 O8 C25 -44.8(12) . . . . ?
O2 Na4 O9 C26 166.3(8) . . . . ?
O2 Na4 O9 C27 -52.2(10) . . . . ?
O2 C13 C14 O3 41.1(8) . . . . ?
C13 C14 O3 Na4 -43.9(6) . . . . ?
C13 C14 O3 C15 173.8(5) . . . . ?
O3 Na4 O1 Na4 -153.45(10) . . . 3_565 ?
O3 Na4 O1 C2 -8.2(2) . . . . ?
O3 Na4 O4 C16 -66.9(4) . . . . ?
O3 Na4 O4 C17 85.7(4) . . . . ?
O3 Na4 O5 C18 -111.1(3) . . . . ?
O3 Na4 O5 C19 114.5(3) . . . . ?
O3 Na4 O2 C12 155.4(5) . . . . ?
O3 Na4 O2 C13 -3.8(4) . . . . ?
O3 Na4 O2A C12A 158.6(13) . . . . ?
O3 Na4 O2A C13A -15.7(9) . . . . ?
O3 Na4 O3A C14A 80.1(11) . . . . ?
O3 Na4 O3A C15A -86.3(11) . . . . ?
O3 Na4 O4A C16A -79.0(13) . . . . ?
O3 Na4 O4A C17A 91.7(12) . . . . ?
O3 Na4 O5A C18A -97.2(9) . . . . ?
O3 Na4 O5A C19A 94.9(10) . . . . ?
O3 Na4 O6 C20 36.4(12) . . . . ?
O3 Na4 O6 C21 -97.9(9) . . . . ?
O3 Na4 C21 O6 71.4(9) . . . . ?
O3 Na4 C21 C22 -145.8(9) . . . . ?
O3 Na4 O7 C22 72.8(8) . . . . ?
O3 Na4 O7 C23 -148.6(10) . . . . ?
O3 Na4 O8 C24 -103.9(11) . . . . ?
O3 Na4 O8 C25 22.4(8) . . . . ?
O3 Na4 O9 C26 -154.6(11) . . . . ?
O3 Na4 O9 C27 -13.1(8) . . . . ?
C12A O2A C13A C14A -176.9(14) . . . . ?
O2A Na4 O1 Na4 -90.0(3) . . . 3_565 ?
O2A Na4 O1 C2 55.2(3) . . . . ?
O2A Na4 O4 C16 -127.4(5) . . . . ?
O2A Na4 O4 C17 25.2(6) . . . . ?
O2A Na4 O5 C18 -178.8(4) . . . . ?
O2A Na4 O5 C19 46.8(4) . . . . ?
O2A Na4 O2 C12 -108(2) . . . . ?
O2A Na4 O2 C13 93(2) . . . . ?
O2A Na4 O3 C14 15.4(4) . . . . ?
O2A Na4 O3 C15 154.2(5) . . . . ?
O2A Na4 O3A C14A -3.7(9) . . . . ?
O2A Na4 O3A C15A -170.1(10) . . . . ?
O2A Na4 O4A C16A -146.9(11) . . . . ?
O2A Na4 O4A C17A 23.8(17) . . . . ?
O2A Na4 O5A C18A -162.6(10) . . . . ?
O2A Na4 O5A C19A 29.4(10) . . . . ?
O2A Na4 O6 C20 -171(7) . . . . ?
O2A Na4 O6 C21 55(5) . . . . ?
O2A Na4 C21 O6 -11.2(11) . . . . ?
O2A Na4 C21 C22 131.5(14) . . . . ?
O2A Na4 O7 C22 10.3(8) . . . . ?
O2A Na4 O7 C23 148.9(11) . . . . ?
O2A Na4 O8 C24 -175.5(9) . . . . ?
O2A Na4 O8 C25 -49.2(11) . . . . ?
O2A Na4 O9 C26 158.4(9) . . . . ?
O2A Na4 O9 C27 -60.1(10) . . . . ?
O2A C13A C14A O3A -2(2) . . . . ?
C13A C14A O3A Na4 4.6(18) . . . . ?
C13A C14A O3A C15A 170.9(14) . . . . ?
O3A Na4 O1 Na4 -163.8(2) . . . 3_565 ?
O3A Na4 O1 C2 -18.5(3) . . . . ?
O3A Na4 O4 C16 -80.7(4) . . . . ?
O3A Na4 O4 C17 71.9(4) . . . . ?
O3A Na4 O5 C18 -106.2(4) . . . . ?
O3A Na4 O5 C19 119.4(4) . . . . ?
O3A Na4 O2 C12 173.6(5) . . . . ?
O3A Na4 O2 C13 14.3(4) . . . . ?
O3A Na4 O3 C14 -74.2(8) . . . . ?
O3A Na4 O3 C15 64.6(8) . . . . ?
O3A Na4 O2A C12A 177.1(13) . . . . ?
O3A Na4 O2A C13A 2.8(9) . . . . ?
O3A Na4 O4A C16A -93.1(13) . . . . ?
O3A Na4 O4A C17A 77.5(12) . . . . ?
O3A Na4 O5A C18A -92.9(9) . . . . ?
O3A Na4 O5A C19A 99.1(10) . . . . ?
O3A Na4 O6 C20 55.5(12) . . . . ?
O3A Na4 O6 C21 -78.9(9) . . . . ?
O3A Na4 C21 O6 88.9(9) . . . . ?
O3A Na4 C21 C22 -128.3(9) . . . . ?
O3A Na4 O7 C22 80.7(8) . . . . ?
O3A Na4 O7 C23 -140.8(10) . . . . ?
O3A Na4 O8 C24 -117.2(11) . . . . ?
O3A Na4 O8 C25 9.1(8) . . . . ?
O3A Na4 O9 C26 173.1(14) . . . . ?
O3A Na4 O9 C27 -45.3(11) . . . . ?
C16A O4A C17A C18A -164.5(15) . . . . ?
O4A Na4 O1 Na4 106.4(4) . . . 3_565 ?
O4A Na4 O1 C2 -108.3(4) . . . . ?
O4A Na4 O4 C16 95(3) . . . . ?
O4A Na4 O4 C17 -112(3) . . . . ?
O4A Na4 O5 C18 -11.1(5) . . . . ?
O4A Na4 O5 C19 -145.5(5) . . . . ?
O4A Na4 O2 C12 -135.5(9) . . . . ?
O4A Na4 O2 C13 65.2(10) . . . . ?
O4A Na4 O3 C14 -129.3(4) . . . . ?
O4A Na4 O3 C15 9.6(5) . . . . ?
O4A Na4 O2A C12A -123.7(13) . . . . ?
O4A Na4 O2A C13A 62.0(13) . . . . ?
O4A Na4 O3A C14A -153.7(9) . . . . ?
O4A Na4 O3A C15A 39.9(10) . . . . ?
O4A Na4 O5A C18A -2.8(10) . . . . ?
O4A Na4 O5A C19A -170.8(11) . . . . ?
O4A Na4 O6 C20 105.6(15) . . . . ?
O4A Na4 O6 C21 -28.7(14) . . . . ?
O4A Na4 C21 O6 161.3(9) . . . . ?
O4A Na4 C21 C22 -56.0(10) . . . . ?
O4A Na4 O7 C22 171.4(9) . . . . ?
O4A Na4 O7 C23 -50.0(11) . . . . ?
O4A Na4 O8 C24 -38(7) . . . . ?
O4A Na4 O8 C25 88(8) . . . . ?
O4A Na4 O9 C26 8.4(8) . . . . ?
O4A Na4 O9 C27 149.9(10) . . . . ?
O4A C17A C18A O5A -28(2) . . . . ?
C17A C18A O5A Na4 17.4(16) . . . . ?
C17A C18A O5A C19A -173.4(12) . . . . ?
C20 O6 C21 Na4 -144.0(14) . . . . ?
C20 O6 C21 C22 173.4(13) . . . . ?
O6 Na4 O1 Na4 -94.5(3) . . . 3_565 ?
O6 Na4 O1 C2 50.7(4) . . . . ?
O6 Na4 O4 C16 -119.2(6) . . . . ?
O6 Na4 O4 C17 33.4(7) . . . . ?
O6 Na4 O5 C18 -174.3(4) . . . . ?
O6 Na4 O5 C19 51.3(4) . . . . ?
O6 Na4 O2 C12 -149(4) . . . . ?
O6 Na4 O2 C13 52(3) . . . . ?
O6 Na4 O3 C14 18.0(5) . . . . ?
O6 Na4 O3 C15 156.9(5) . . . . ?
O6 Na4 O2A C12A 132(6) . . . . ?
O6 Na4 O2A C13A -42(5) . . . . ?
O6 Na4 O3A C14A 0.4(9) . . . . ?
O6 Na4 O3A C15A -166.0(10) . . . . ?
O6 Na4 O4A C16A -137.7(12) . . . . ?
O6 Na4 O4A C17A 32.9(17) . . . . ?
O6 Na4 O5A C18A -159.0(10) . . . . ?
O6 Na4 O5A C19A 33.0(10) . . . . ?
O6 Na4 C21 C22 142.8(14) . . . . ?
O6 Na4 O7 C22 14.1(8) . . . . ?
O6 Na4 O7 C23 152.7(11) . . . . ?
O6 Na4 O8 C24 -167.3(10) . . . . ?
O6 Na4 O8 C25 -40.9(11) . . . . ?
O6 Na4 O9 C26 162.5(9) . . . . ?
O6 Na4 O9 C27 -56.0(10) . . . . ?
O6 C21 C22 O7 58.8(17) . . . . ?
C21 C22 O7 Na4 -38.7(13) . . . . ?
C21 C22 O7 C23 174.5(11) . . . . ?
O7 Na4 O1 Na4 71.7(11) . . . 3_565 ?
O7 Na4 O1 C2 -143.1(11) . . . . ?
O7 Na4 O4 C16 -167.1(5) . . . . ?
O7 Na4 O4 C17 -14.5(4) . . . . ?
O7 Na4 O5 C18 120.8(12) . . . . ?
O7 Na4 O5 C19 -13.6(10) . . . . ?
O7 Na4 O2 C12 -97.3(5) . . . . ?
O7 Na4 O2 C13 103.4(5) . . . . ?
O7 Na4 O3 C14 -47.1(4) . . . . ?
O7 Na4 O3 C15 91.8(4) . . . . ?
O7 Na4 O2A C12A -90.5(12) . . . . ?
O7 Na4 O2A C13A 95.2(10) . . . . ?
O7 Na4 O3A C14A -73.1(9) . . . . ?
O7 Na4 O3A C15A 120.5(10) . . . . ?
O7 Na4 O4A C16A -178.1(14) . . . . ?
O7 Na4 O4A C17A -7.4(11) . . . . ?
O7 Na4 O5A C18A -163(2) . . . . ?
O7 Na4 O5A C19A 29.2(14) . . . . ?
O7 Na4 O6 C20 147.5(13) . . . . ?
O7 Na4 O6 C21 13.2(8) . . . . ?
O7 Na4 C21 O6 -162.9(11) . . . . ?
O7 Na4 C21 C22 -20.2(7) . . . . ?
O7 Na4 O8 C24 158.2(12) . . . . ?
O7 Na4 O8 C25 -75.5(8) . . . . ?
O7 Na4 O9 C26 89.4(8) . . . . ?
O7 Na4 O9 C27 -129.0(10) . . . . ?
C24 O8 C25 C26 83.1(16) . . . . ?
O8 Na4 O1 Na4 104.5(4) . . . 3_565 ?
O8 Na4 O1 C2 -110.3(4) . . . . ?
O8 Na4 O4 C16 126(2) . . . . ?
O8 Na4 O4 C17 -82(2) . . . . ?
O8 Na4 O5 C18 -8.7(5) . . . . ?
O8 Na4 O5 C19 -143.1(5) . . . . ?
O8 Na4 O2 C12 -127.8(7) . . . . ?
O8 Na4 O2 C13 72.9(8) . . . . ?
O8 Na4 O3 C14 -124.7(4) . . . . ?
O8 Na4 O3 C15 14.2(5) . . . . ?
O8 Na4 O2A C12A -117.9(13) . . . . ?
O8 Na4 O2A C13A 67.8(12) . . . . ?
O8 Na4 O3A C14A -148.8(9) . . . . ?
O8 Na4 O3A C15A 44.8(10) . . . . ?
O8 Na4 O4A C16A 166(9) . . . . ?
O8 Na4 O4A C17A -23(7) . . . . ?
O8 Na4 O5A C18A -1.7(10) . . . . ?
O8 Na4 O5A C19A -169.7(11) . . . . ?
O8 Na4 O6 C20 112.4(13) . . . . ?
O8 Na4 O6 C21 -21.9(12) . . . . ?
O8 Na4 C21 O6 165.0(9) . . . . ?
O8 Na4 C21 C22 -52.2(9) . . . . ?
O8 Na4 O7 C22 172.9(9) . . . . ?
O8 Na4 O7 C23 -48.6(10) . . . . ?
O8 Na4 O9 C26 13.4(8) . . . . ?
O8 Na4 O9 C27 154.9(10) . . . . ?
O8 C25 C26 O9 59.5(15) . . . . ?
C25 C26 O9 Na4 -41.1(13) . . . . ?
C25 C26 O9 C27 173.4(11) . . . . ?
O9 Na4 O1 Na4 176.3(2) . . . 3_565 ?
O9 Na4 O1 C2 -38.5(3) . . . . ?
O9 Na4 O4 C16 -74.9(5) . . . . ?
O9 Na4 O4 C17 77.7(4) . . . . ?
O9 Na4 O5 C18 -84.9(4) . . . . ?
O9 Na4 O5 C19 140.7(4) . . . . ?
O9 Na4 O2 C12 176.1(5) . . . . ?
O9 Na4 O2 C13 16.9(4) . . . . ?
O9 Na4 O3 C14 -113.1(6) . . . . ?
O9 Na4 O3 C15 25.8(5) . . . . ?
O9 Na4 O2A C12A -177.5(12) . . . . ?
O9 Na4 O2A C13A 8.3(10) . . . . ?
O9 Na4 O3A C14A -168.0(15) . . . . ?
O9 Na4 O3A C15A 25.6(9) . . . . ?
O9 Na4 O4A C16A -87.8(14) . . . . ?
O9 Na4 O4A C17A 82.8(12) . . . . ?
O9 Na4 O5A C18A -72.5(9) . . . . ?
O9 Na4 O5A C19A 119.5(10) . . . . ?
O9 Na4 O6 C20 59.5(13) . . . . ?
O9 Na4 O6 C21 -74.8(9) . . . . ?
O9 Na4 C21 O6 102.1(9) . . . . ?
O9 Na4 C21 C22 -115.1(8) . . . . ?
O9 Na4 O7 C22 101.1(8) . . . . ?
O9 Na4 O7 C23 -120.3(10) . . . . ?
O9 Na4 O8 C24 -110.2(11) . . . . ?
O9 Na4 O8 C25 16.1(8) . . . . ?

_olex2_computing_structure_refinement_long 'SHELXL-97 (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'SHELXS-97 (Sheldrick, 2008)'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dme/MTBE'
_chemical_properties_physical    'Air-sensitive, Oxygen-sensitive'
####################################################################### 
# 
# 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_micha
_database_code_depnum_ccdc_archive 'CCDC 1454790'
_audit_update_record             
;
2016-02-19 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;
_audit_creation_date             2016-01-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
1-thio-2,4-diphospholo-5-mesityl-3-mesitoylester
_chemical_formula_moiety         'C21 H22 O2 P2 S'
_chemical_formula_sum            'C21 H22 O2 P2 S'
_chemical_formula_weight         400.38
_chemical_melting_point          '389 K'
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'

_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                   7.1716(4)
_cell_length_b                   8.4029(7)
_cell_length_c                   17.181(2)
_cell_angle_alpha                80.076(9)
_cell_angle_beta                 88.792(8)
_cell_angle_gamma                86.067(6)
_cell_volume                     1017.46(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2561
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.5830
_cell_measurement_theta_min      3.1280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92478
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6195
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.092
_diffrn_reflns_theta_min         2.847
_diffrn_ambient_temperature      100
_diffrn_detector                 'Oxford Diffraction Sapphire 3'
_diffrn_detector_area_resol_mean 8.26
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'focusing graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3885
_reflns_number_total             6195
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         6195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      0.898
_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)+(0.0459P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1102
_refine_special_details          Twin
_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
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C15(H15), C19(H19)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_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
P1 P 0.91307(12) 0.75915(12) 0.30403(5) 0.0240(2) Uani 1 1 d . . . . .
S2 S 0.50705(11) 0.74633(12) 0.33652(6) 0.0300(3) Uani 1 1 d . . . . .
P3 P 0.54514(12) 0.72689(12) 0.21756(6) 0.0291(3) Uani 1 1 d . . . . .
O1 O 0.9012(3) 0.7412(3) 0.15373(13) 0.0230(6) Uani 1 1 d . . . . .
O2 O 0.6562(3) 0.7222(3) 0.07742(14) 0.0297(6) Uani 1 1 d . . . . .
C3 C 0.7842(4) 0.7405(4) 0.2203(2) 0.0212(8) Uani 1 1 d . . . . .
C4 C 0.7493(4) 0.9274(4) 0.4759(2) 0.0208(8) Uani 1 1 d . . . . .
C5 C 0.7462(4) 0.7746(4) 0.4535(2) 0.0208(8) Uani 1 1 d . . . . .
C6 C 1.1313(4) 0.6495(4) 0.0233(2) 0.0204(8) Uani 1 1 d . . . . .
C7 C 0.9627(4) 0.7471(4) 0.01658(19) 0.0197(8) Uani 1 1 d . . . . .
C8 C 0.9153(4) 0.8550(4) -0.05278(19) 0.0208(8) Uani 1 1 d . . . . .
C9 C 0.8232(5) 0.7342(4) 0.0828(2) 0.0224(8) Uani 1 1 d . . . . .
C10 C 1.0415(4) 0.8630(4) -0.1153(2) 0.0243(8) Uani 1 1 d . . . . .
H10 H 1.0126 0.9365 -0.1626 0.029 Uiso 1 1 calc R . . . .
C11 C 0.7797(4) 0.7958(5) 0.6132(2) 0.0242(9) Uani 1 1 d . . . . .
C12 C 1.2085(4) 0.7679(4) -0.1117(2) 0.0236(8) Uani 1 1 d . . . . .
C13 C 1.2489(4) 0.6628(4) -0.0426(2) 0.0248(9) Uani 1 1 d . . . . .
H13 H 1.3620 0.5964 -0.0397 0.030 Uiso 1 1 calc R . . . .
C14 C 1.3388(5) 0.7764(5) -0.1821(2) 0.0356(10) Uani 1 1 d . . . . .
H14A H 1.3177 0.6879 -0.2106 0.053 Uiso 1 1 calc GR . . . .
H14B H 1.4685 0.7666 -0.1642 0.053 Uiso 1 1 calc GR . . . .
H14C H 1.3148 0.8804 -0.2174 0.053 Uiso 1 1 calc GR . . . .
C15 C 0.7725(4) 0.6475(4) 0.5896(2) 0.0263(9) Uani 1 1 d . . . . .
H15 H 0.7786 0.5523 0.6286 0.032 Uiso 1 1 calc R . . . .
C16 C 0.7565(4) 0.6326(4) 0.5100(2) 0.0233(9) Uani 1 1 d . . . . .
C17 C 0.7371(4) 0.9617(4) -0.0616(2) 0.0297(9) Uani 1 1 d . . . . .
H17A H 0.6314 0.8957 -0.0658 0.045 Uiso 1 1 calc GR . . . .
H17B H 0.7448 1.0436 -0.1095 0.045 Uiso 1 1 calc GR . . . .
H17C H 0.7189 1.0153 -0.0155 0.045 Uiso 1 1 calc GR . . . .
C18 C 0.7277(4) 0.7613(4) 0.3680(2) 0.0226(8) Uani 1 1 d . . . . .
C19 C 0.7678(4) 0.9336(5) 0.5559(2) 0.0257(9) Uani 1 1 d . . . . .
H19 H 0.7724 1.0362 0.5716 0.031 Uiso 1 1 calc R . . . .
C20 C 1.1840(4) 0.5314(4) 0.0965(2) 0.0250(9) Uani 1 1 d . . . . .
H20A H 1.2299 0.5897 0.1362 0.037 Uiso 1 1 calc GR . . . .
H20B H 1.2824 0.4530 0.0837 0.037 Uiso 1 1 calc GR . . . .
H20C H 1.0742 0.4743 0.1175 0.037 Uiso 1 1 calc GR . . . .
C21 C 0.7559(4) 0.4683(4) 0.4871(2) 0.0279(9) Uani 1 1 d . . . . .
H21A H 0.6337 0.4551 0.4654 0.042 Uiso 1 1 calc GR . . . .
H21B H 0.7804 0.3849 0.5337 0.042 Uiso 1 1 calc GR . . . .
H21C H 0.8532 0.4576 0.4471 0.042 Uiso 1 1 calc GR . . . .
C22 C 0.7317(4) 1.0812(4) 0.4172(2) 0.0294(9) Uani 1 1 d . . . . .
H22A H 0.8554 1.1078 0.3956 0.044 Uiso 1 1 calc GR . . . .
H22B H 0.6784 1.1691 0.4433 0.044 Uiso 1 1 calc GR . . . .
H22C H 0.6496 1.0675 0.3743 0.044 Uiso 1 1 calc GR . . . .
C23 C 0.8003(5) 0.8062(5) 0.6993(2) 0.0375(10) Uani 1 1 d . . . . .
H23A H 0.7524 0.7100 0.7320 0.056 Uiso 1 1 calc GR . . . .
H23B H 0.7292 0.9034 0.7109 0.056 Uiso 1 1 calc GR . . . .
H23C H 0.9325 0.8121 0.7110 0.056 Uiso 1 1 calc 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
P1 C3 1.761(3) . ?
P1 C18 1.708(3) . ?
S2 P3 2.0892(14) . ?
S2 C18 1.702(3) . ?
P3 C3 1.729(3) . ?
O1 C3 1.404(4) . ?
O1 C9 1.364(4) . ?
O2 C9 1.215(3) . ?
C4 C5 1.404(5) . ?
C4 C19 1.394(5) . ?
C4 C22 1.495(5) . ?
C5 C16 1.401(5) . ?
C5 C18 1.502(5) . ?
C6 C7 1.409(4) . ?
C6 C13 1.391(4) . ?
C6 C20 1.499(4) . ?
C7 C8 1.400(4) . ?
C7 C9 1.493(4) . ?
C8 C10 1.386(4) . ?
C8 C17 1.505(4) . ?
C10 H10 0.9500 . ?
C10 C12 1.390(5) . ?
C11 C15 1.379(5) . ?
C11 C19 1.385(5) . ?
C11 C23 1.508(4) . ?
C12 C13 1.376(5) . ?
C12 C14 1.508(4) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C16 1.402(5) . ?
C16 C21 1.500(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 P1 C3 96.81(15) . . ?
C18 S2 P3 103.55(13) . . ?
C3 P3 S2 93.50(12) . . ?
C9 O1 C3 118.8(2) . . ?
P3 C3 P1 125.76(19) . . ?
O1 C3 P1 111.0(2) . . ?
O1 C3 P3 123.2(2) . . ?
C5 C4 C22 122.3(3) . . ?
C19 C4 C5 118.0(3) . . ?
C19 C4 C22 119.7(3) . . ?
C4 C5 C18 120.1(3) . . ?
C16 C5 C4 121.1(3) . . ?
C16 C5 C18 118.8(3) . . ?
C7 C6 C20 122.9(3) . . ?
C13 C6 C7 117.2(3) . . ?
C13 C6 C20 119.9(3) . . ?
C6 C7 C9 120.8(3) . . ?
C8 C7 C6 121.9(3) . . ?
C8 C7 C9 117.2(3) . . ?
C7 C8 C17 123.2(3) . . ?
C10 C8 C7 117.4(3) . . ?
C10 C8 C17 119.4(3) . . ?
O1 C9 C7 112.8(3) . . ?
O2 C9 O1 120.8(3) . . ?
O2 C9 C7 126.4(3) . . ?
C8 C10 H10 118.6 . . ?
C8 C10 C12 122.8(3) . . ?
C12 C10 H10 118.6 . . ?
C15 C11 C19 118.2(3) . . ?
C15 C11 C23 120.5(3) . . ?
C19 C11 C23 121.3(3) . . ?
C10 C12 C14 121.0(3) . . ?
C13 C12 C10 117.9(3) . . ?
C13 C12 C14 121.1(3) . . ?
C6 C13 H13 118.6 . . ?
C12 C13 C6 122.9(3) . . ?
C12 C13 H13 118.6 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15 118.9 . . ?
C11 C15 C16 122.2(3) . . ?
C16 C15 H15 118.9 . . ?
C5 C16 C15 118.0(3) . . ?
C5 C16 C21 121.8(3) . . ?
C15 C16 C21 120.2(3) . . ?
C8 C17 H17A 109.5 . . ?
C8 C17 H17B 109.5 . . ?
C8 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S2 C18 P1 120.4(2) . . ?
C5 C18 P1 123.5(2) . . ?
C5 C18 S2 116.1(2) . . ?
C4 C19 H19 118.8 . . ?
C11 C19 C4 122.5(4) . . ?
C11 C19 H19 118.8 . . ?
C6 C20 H20A 109.5 . . ?
C6 C20 H20B 109.5 . . ?
C6 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 C22 H22A 109.5 . . ?
C4 C22 H22B 109.5 . . ?
C4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C23 H23A 109.5 . . ?
C11 C23 H23B 109.5 . . ?
C11 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
S2 P3 C3 P1 1.2(2) . . . . ?
S2 P3 C3 O1 -177.5(3) . . . . ?
P3 S2 C18 P1 0.4(2) . . . . ?
P3 S2 C18 C5 -179.1(2) . . . . ?
C3 P1 C18 S2 0.2(2) . . . . ?
C3 P1 C18 C5 179.6(3) . . . . ?
C3 O1 C9 O2 -2.4(4) . . . . ?
C3 O1 C9 C7 176.1(3) . . . . ?
C4 C5 C16 C15 -0.8(4) . . . . ?
C4 C5 C16 C21 -179.2(3) . . . . ?
C4 C5 C18 P1 85.7(4) . . . . ?
C4 C5 C18 S2 -94.9(3) . . . . ?
C5 C4 C19 C11 -1.1(5) . . . . ?
C6 C7 C8 C10 -0.2(5) . . . . ?
C6 C7 C8 C17 -179.5(3) . . . . ?
C6 C7 C9 O1 49.7(4) . . . . ?
C6 C7 C9 O2 -131.9(4) . . . . ?
C7 C6 C13 C12 1.3(5) . . . . ?
C7 C8 C10 C12 0.9(5) . . . . ?
C8 C7 C9 O1 -132.8(3) . . . . ?
C8 C7 C9 O2 45.6(5) . . . . ?
C8 C10 C12 C13 -0.5(5) . . . . ?
C8 C10 C12 C14 177.9(3) . . . . ?
C9 O1 C3 P1 -177.4(2) . . . . ?
C9 O1 C3 P3 1.4(4) . . . . ?
C9 C7 C8 C10 -177.7(3) . . . . ?
C9 C7 C8 C17 2.9(4) . . . . ?
C10 C12 C13 C6 -0.7(5) . . . . ?
C11 C15 C16 C5 -0.5(5) . . . . ?
C11 C15 C16 C21 177.9(3) . . . . ?
C13 C6 C7 C8 -0.9(5) . . . . ?
C13 C6 C7 C9 176.6(3) . . . . ?
C14 C12 C13 C6 -179.1(3) . . . . ?
C15 C11 C19 C4 -0.1(5) . . . . ?
C16 C5 C18 P1 -95.6(3) . . . . ?
C16 C5 C18 S2 83.9(3) . . . . ?
C17 C8 C10 C12 -179.7(3) . . . . ?
C18 P1 C3 P3 -1.0(2) . . . . ?
C18 P1 C3 O1 177.8(2) . . . . ?
C18 C5 C16 C15 -179.6(3) . . . . ?
C18 C5 C16 C21 2.1(4) . . . . ?
C19 C4 C5 C16 1.6(4) . . . . ?
C19 C4 C5 C18 -179.6(3) . . . . ?
C19 C11 C15 C16 1.0(5) . . . . ?
C20 C6 C7 C8 -179.1(3) . . . . ?
C20 C6 C7 C9 -1.6(5) . . . . ?
C20 C6 C13 C12 179.6(3) . . . . ?
C22 C4 C5 C16 -177.8(3) . . . . ?
C22 C4 C5 C18 1.0(4) . . . . ?
C22 C4 C19 C11 178.3(3) . . . . ?
C23 C11 C15 C16 -179.0(3) . . . . ?
C23 C11 C19 C4 179.8(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
_chemical_properties_physical    
'Air-sensitive, Oxygen-sensitive, Light-sensitive'
