# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

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

data_190414d
_database_code_depnum_ccdc_archive 'CCDC 1975582'
loop_
_audit_author_name
_audit_author_address
'XiaoNing Wang'
;Liaocheng University
China
;
_audit_update_record             
;
2020-01-06 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H30 Cl3 O2 P S'
_chemical_formula_weight         507.85

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   9.8758(8)
_cell_length_b                   10.6484(9)
_cell_length_c                   12.6525(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.229(2)
_cell_angle_gamma                90
_cell_volume                     1309.41(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2091
_cell_measurement_theta_min      2.417
_cell_measurement_theta_max      22.353

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.508
_shelx_estimated_absorpt_T_min   0.830
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6657
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.419
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.865
_reflns_number_total             4092
_reflns_number_gt                3000
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_max     0.757
_reflns_Friedel_fraction_full    0.740

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0521P)²+0.5520P] 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_abs_structure_details 
;
 Flack x determined using 1052 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_chemical_absolute_configuration R
_refine_ls_number_reflns         4092
_refine_ls_number_parameters     276
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.002
_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
P1 P 0.68153(14) 0.99591(14) 0.64143(11) 0.0430(4) Uani 1 1 d . . . . .
S1 S 0.64871(16) 1.17335(15) 0.60713(13) 0.0595(5) Uani 1 1 d . . . . .
O1 O 0.6647(4) 0.6960(4) 0.5052(3) 0.0569(11) Uani 1 1 d . . . . .
H1 H 0.5943 0.6607 0.4757 0.085 Uiso 1 1 calc R U . . .
O2 O 0.5716(4) 0.9128(4) 0.5659(3) 0.0580(11) Uani 1 1 d . . . . .
H2 H 0.6105 0.8543 0.5417 0.087 Uiso 1 1 calc R U . . .
C3 C 0.8485(5) 0.9403(5) 0.6190(4) 0.0394(13) Uani 1 1 d . . . . .
C4 C 0.8924(5) 0.8143(5) 0.6351(4) 0.0440(14) Uani 1 1 d . . . . .
C5 C 0.8127(5) 0.7097(5) 0.6742(4) 0.0440(14) Uani 1 1 d . . . . .
C6 C 0.8669(6) 1.0948(7) 0.8653(5) 0.0545(16) Uani 1 1 d . . . . .
H6 H 0.8763 1.1139 0.7912 0.065 Uiso 1 1 calc R U . . .
C7 C 0.7028(6) 0.6499(6) 0.6093(4) 0.0463(14) Uani 1 1 d . . . . .
C8 C 0.6614(5) 0.9570(5) 0.7782(5) 0.0486(15) Uani 1 1 d . . . . .
H8 H 0.7146 0.8803 0.7986 0.058 Uiso 1 1 calc R U . . .
C9 C 0.6758(7) 0.5068(7) 0.7485(6) 0.0731(19) Uani 1 1 d . . . . .
H9 H 0.6286 0.4409 0.7739 0.088 Uiso 1 1 calc R U . . .
C10 C 0.8522(6) 0.6627(6) 0.7769(5) 0.0594(17) Uani 1 1 d . . . . .
H10 H 0.9259 0.6997 0.8221 0.071 Uiso 1 1 calc R U . . .
C11 C 1.0232(6) 0.7840(7) 0.6151(6) 0.0625(18) Uani 1 1 d . . . . .
H11 H 1.0537 0.7014 0.6241 0.075 Uiso 1 1 calc R U . . .
C12 C 0.9361(6) 1.0264(6) 0.5862(5) 0.0557(17) Uani 1 1 d . . . . .
H12 H 0.9075 1.1093 0.5759 0.067 Uiso 1 1 calc R U . . .
C13 C 0.7155(6) 1.0575(6) 0.8620(5) 0.0554(17) Uani 1 1 d . . . . .
H13 H 0.6599 1.1331 0.8431 0.066 Uiso 1 1 calc R U . . .
C14 C 0.9705(7) 0.9915(8) 0.9038(6) 0.081(2) Uani 1 1 d . . . . .
H14A H 1.0616 1.0206 0.9000 0.122 Uiso 1 1 calc R U . . .
H14B H 0.9499 0.9188 0.8590 0.122 Uiso 1 1 calc R U . . .
H14C H 0.9656 0.9700 0.9767 0.122 Uiso 1 1 calc R U . . .
C15 C 1.0647(7) 0.9936(8) 0.5683(6) 0.0736(19) Uani 1 1 d . . . . .
H15 H 1.1222 1.0537 0.5465 0.088 Uiso 1 1 calc R U . . .
C16 C 0.6376(7) 0.5500(6) 0.6457(6) 0.068(2) Uani 1 1 d . . . . .
H16 H 0.5661 0.5106 0.5998 0.082 Uiso 1 1 calc R U . . .
C17 C 0.6885(8) 1.0133(9) 0.9716(5) 0.086(2) Uani 1 1 d . . . . .
H17A H 0.7398 0.9367 0.9917 0.104 Uiso 1 1 calc R U . . .
H17B H 0.7212 1.0766 1.0252 0.104 Uiso 1 1 calc R U . . .
C18 C 0.9034(8) 1.2147(7) 0.9296(5) 0.078(2) Uani 1 1 d . . . . .
H18A H 0.8450 1.2818 0.8979 0.117 Uiso 1 1 calc R U . . .
H18B H 0.9977 1.2360 0.9293 0.117 Uiso 1 1 calc R U . . .
H18C H 0.8903 1.2019 1.0023 0.117 Uiso 1 1 calc R U . . .
C19 C 0.7863(8) 0.5635(7) 0.8141(6) 0.074(2) Uani 1 1 d . . . . .
H19 H 0.8156 0.5340 0.8836 0.089 Uiso 1 1 calc R U . . .
C20 C 1.1072(7) 0.8721(9) 0.5830(6) 0.077(2) Uani 1 1 d . . . . .
H20 H 1.1940 0.8492 0.5709 0.093 Uiso 1 1 calc R U . . .
C21 C 0.4833(8) 0.8869(9) 0.8890(7) 0.084(2) Uani 1 1 d . . . . .
H21 H 0.5345 0.8094 0.9099 0.101 Uiso 1 1 calc R U . . .
C22 C 0.5094(6) 0.9257(7) 0.7798(6) 0.0655(18) Uani 1 1 d . . . . .
H22A H 0.4536 0.9988 0.7560 0.079 Uiso 1 1 calc R U . . .
H22B H 0.4805 0.8584 0.7292 0.079 Uiso 1 1 calc R U . . .
C23 C 0.5378(9) 0.9893(11) 0.9706(7) 0.107(3) Uani 1 1 d . . . . .
H23A H 0.4864 1.0662 0.9523 0.128 Uiso 1 1 calc R U . . .
H23B H 0.5247 0.9635 1.0416 0.128 Uiso 1 1 calc R U . . .
C24 C 0.3286(9) 0.8603(12) 0.8848(9) 0.142(4) Uani 1 1 d . . . . .
H24A H 0.2750 0.9231 0.8418 0.213 Uiso 1 1 calc R U . . .
H24B H 0.3084 0.8622 0.9563 0.213 Uiso 1 1 calc R U . . .
H24C H 0.3063 0.7789 0.8538 0.213 Uiso 1 1 calc R U . . .
Cl1 Cl 0.2900(3) 0.4896(4) 0.6923(3) 0.1570(13) Uani 1 1 d . . . . .
Cl2 Cl 0.0367(3) 0.3844(4) 0.7149(3) 0.1585(14) Uani 1 1 d . . . . .
Cl3 Cl 0.2805(5) 0.2449(4) 0.7774(3) 0.1939(18) Uani 1 1 d . . . . .
C28 C 0.1938(10) 0.3517(9) 0.6894(7) 0.104(3) Uani 1 1 d . . . . .
H28 H 0.1832 0.3162 0.6169 0.125 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.583(4) . ?
P1 C3 1.821(5) . ?
P1 C8 1.824(6) . ?
P1 S1 1.953(2) . ?
O1 C7 1.393(7) . ?
O1 H1 0.8200 . ?
O2 H2 0.8200 . ?
C3 C12 1.373(8) . ?
C3 C4 1.413(8) . ?
C4 C11 1.397(8) . ?
C4 C5 1.498(8) . ?
C5 C10 1.383(8) . ?
C5 C7 1.393(7) . ?
C6 C18 1.523(9) . ?
C6 C14 1.522(9) . ?
C6 C13 1.541(9) . ?
C6 H6 0.9800 . ?
C7 C16 1.366(8) . ?
C8 C13 1.534(8) . ?
C8 C22 1.542(8) . ?
C8 H8 0.9800 . ?
C9 C16 1.368(9) . ?
C9 C19 1.386(10) . ?
C9 H9 0.9300 . ?
C10 C19 1.368(9) . ?
C10 H10 0.9300 . ?
C11 C20 1.361(10) . ?
C11 H11 0.9300 . ?
C12 C15 1.375(9) . ?
C12 H12 0.9300 . ?
C13 C17 1.532(8) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.362(11) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C23 1.507(11) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.508(10) . ?
C21 C23 1.532(12) . ?
C21 C24 1.545(11) . ?
C21 H21 0.9800 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
Cl1 C28 1.746(11) . ?
Cl2 C28 1.676(9) . ?
Cl3 C28 1.710(10) . ?
C28 H28 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
O2 P1 C3 105.5(2) . . ?
O2 P1 C8 105.5(3) . . ?
C3 P1 C8 109.2(2) . . ?
O2 P1 S1 109.73(18) . . ?
C3 P1 S1 113.5(2) . . ?
C8 P1 S1 112.9(2) . . ?
C7 O1 H1 109.5 . . ?
P1 O2 H2 109.5 . . ?
C12 C3 C4 118.9(5) . . ?
C12 C3 P1 117.8(4) . . ?
C4 C3 P1 123.3(4) . . ?
C11 C4 C3 117.6(5) . . ?
C11 C4 C5 116.4(5) . . ?
C3 C4 C5 126.0(5) . . ?
C10 C5 C7 116.7(5) . . ?
C10 C5 C4 120.2(5) . . ?
C7 C5 C4 123.0(5) . . ?
C18 C6 C14 110.7(5) . . ?
C18 C6 C13 111.5(5) . . ?
C14 C6 C13 114.6(6) . . ?
C18 C6 H6 106.5 . . ?
C14 C6 H6 106.5 . . ?
C13 C6 H6 106.5 . . ?
C16 C7 O1 121.9(5) . . ?
C16 C7 C5 121.5(5) . . ?
O1 C7 C5 116.6(5) . . ?
C13 C8 C22 111.2(5) . . ?
C13 C8 P1 114.4(4) . . ?
C22 C8 P1 109.4(4) . . ?
C13 C8 H8 107.2 . . ?
C22 C8 H8 107.2 . . ?
P1 C8 H8 107.2 . . ?
C16 C9 C19 118.6(7) . . ?
C16 C9 H9 120.7 . . ?
C19 C9 H9 120.7 . . ?
C19 C10 C5 122.1(6) . . ?
C19 C10 H10 118.9 . . ?
C5 C10 H10 118.9 . . ?
C20 C11 C4 121.8(7) . . ?
C20 C11 H11 119.1 . . ?
C4 C11 H11 119.1 . . ?
C3 C12 C15 122.0(7) . . ?
C3 C12 H12 119.0 . . ?
C15 C12 H12 119.0 . . ?
C17 C13 C8 108.4(6) . . ?
C17 C13 C6 112.3(6) . . ?
C8 C13 C6 114.5(4) . . ?
C17 C13 H13 107.1 . . ?
C8 C13 H13 107.1 . . ?
C6 C13 H13 107.1 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C12 119.3(7) . . ?
C20 C15 H15 120.3 . . ?
C12 C15 H15 120.3 . . ?
C7 C16 C9 121.0(6) . . ?
C7 C16 H16 119.5 . . ?
C9 C16 H16 119.5 . . ?
C23 C17 C13 112.0(6) . . ?
C23 C17 H17A 109.2 . . ?
C13 C17 H17A 109.2 . . ?
C23 C17 H17B 109.2 . . ?
C13 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C6 C18 H18A 109.5 . . ?
C6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 C9 120.1(7) . . ?
C10 C19 H19 120.0 . . ?
C9 C19 H19 120.0 . . ?
C15 C20 C11 120.4(7) . . ?
C15 C20 H20 119.8 . . ?
C11 C20 H20 119.8 . . ?
C22 C21 C23 109.0(6) . . ?
C22 C21 C24 110.4(7) . . ?
C23 C21 C24 112.4(8) . . ?
C22 C21 H21 108.3 . . ?
C23 C21 H21 108.3 . . ?
C24 C21 H21 108.3 . . ?
C21 C22 C8 113.3(6) . . ?
C21 C22 H22A 108.9 . . ?
C8 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C8 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C17 C23 C21 110.8(7) . . ?
C17 C23 H23A 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Cl2 C28 Cl3 112.7(6) . . ?
Cl2 C28 Cl1 109.9(6) . . ?
Cl3 C28 Cl1 109.8(6) . . ?
Cl2 C28 H28 108.1 . . ?
Cl3 C28 H28 108.1 . . ?
Cl1 C28 H28 108.1 . . ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.048

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_200617d
_database_code_depnum_ccdc_archive 'CCDC 2010827'
loop_
_audit_author_name
_audit_author_address
'XiaoNing Wang'
;Liaocheng University
China
;
_audit_update_record             
;
2020-06-19 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H27 O2 P'
_chemical_formula_weight         354.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   8.6104(9)
_cell_length_b                   5.6083(6)
_cell_length_c                   19.2726(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.639(3)
_cell_angle_gamma                90
_cell_volume                     929.68(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1586
_cell_measurement_theta_min      2.367
_cell_measurement_theta_max      27.462

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   0.957
_exptl_transmission_factor_max   0.984
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.160
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4515
_diffrn_reflns_av_unetI/netI     0.1246
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.368
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_full        25.017
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.916
_reflns_number_total             3013
_reflns_number_gt                2122
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_max     0.828
_reflns_Friedel_fraction_full    0.828

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0407P)²+0.5053P] 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_abs_structure_details 
;
 Flack x determined using 557 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(19)
_chemical_absolute_configuration R
_refine_ls_number_reflns         3013
_refine_ls_number_parameters     229
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0789
_refine_ls_wR_factor_ref         0.1669
_refine_ls_wR_factor_gt          0.1500
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.002
_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
P1 P 0.1398(2) 0.8012(4) 0.27022(10) 0.0298(5) Uani 1 1 d . . . . .
O2 O 0.0393(5) 0.7026(9) 0.3328(2) 0.0332(14) Uani 1 1 d . . . . .
O1 O 0.0919(6) 1.0410(10) 0.2490(3) 0.0434(16) Uani 1 1 d . . . . .
C3 C 0.1181(8) 0.5788(14) 0.2035(3) 0.0247(18) Uani 1 1 d . . . . .
H3 H 0.098676 0.425839 0.226040 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2461(9) 0.4713(14) 0.3869(3) 0.029(2) Uani 1 1 d . . . . .
C5 C 0.3310(8) 0.7950(17) 0.3105(3) 0.0315(17) Uani 1 1 d . . . . .
C6 C -0.0197(8) 0.6293(14) 0.1522(4) 0.0281(19) Uani 1 1 d . . . . .
H6 H 0.005476 0.775589 0.127301 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3650(9) 0.6352(14) 0.3639(4) 0.0288(19) Uani 1 1 d . . . . .
C8 C -0.0247(10) 0.3662(14) 0.3959(4) 0.034(2) Uani 1 1 d . . . . .
H8 H -0.128594 0.398973 0.384441 0.041 Uiso 1 1 calc R U . . .
C9 C -0.0316(9) 0.4324(18) 0.0989(4) 0.041(2) Uani 1 1 d . . . . .
H9A H -0.117636 0.465981 0.066038 0.049 Uiso 1 1 calc R U . . .
H9B H -0.053505 0.283133 0.121878 0.049 Uiso 1 1 calc R U . . .
C10 C 0.4405(10) 0.9543(16) 0.2904(4) 0.042(2) Uani 1 1 d . . . . .
H10 H 0.415833 1.060776 0.254563 0.051 Uiso 1 1 calc R U . . .
C11 C 0.0893(9) 0.5097(14) 0.3722(3) 0.0269(18) Uani 1 1 d . . . . .
C12 C 0.5120(10) 0.6491(18) 0.3966(4) 0.049(3) Uani 1 1 d . . . . .
H12 H 0.537507 0.547902 0.433583 0.059 Uiso 1 1 calc R U . . .
C13 C 0.2817(10) 0.2706(17) 0.4267(4) 0.039(2) Uani 1 1 d . . . . .
H13 H 0.385538 0.233940 0.437047 0.047 Uiso 1 1 calc R U . . .
C14 C 0.0145(11) 0.1750(16) 0.4364(4) 0.041(2) Uani 1 1 d . . . . .
H14 H -0.062277 0.078578 0.453990 0.049 Uiso 1 1 calc R U . . .
C15 C 0.2516(9) 0.3598(14) 0.1096(4) 0.036(2) Uani 1 1 d . . . . .
H15 H 0.230146 0.210786 0.133902 0.043 Uiso 1 1 calc R U . . .
C16 C 0.2673(9) 0.5528(16) 0.1634(4) 0.035(2) Uani 1 1 d . . . . .
H16A H 0.289927 0.702881 0.140984 0.042 Uiso 1 1 calc R U . . .
H16B H 0.353601 0.515696 0.195733 0.042 Uiso 1 1 calc R U . . .
C17 C -0.2406(10) 0.4540(17) 0.2188(5) 0.049(2) Uani 1 1 d . . . . .
H17A H -0.325464 0.496139 0.247035 0.074 Uiso 1 1 calc R U . . .
H17B H -0.161033 0.376129 0.247014 0.074 Uiso 1 1 calc R U . . .
H17C H -0.277182 0.348161 0.182469 0.074 Uiso 1 1 calc R U . . .
C18 C 0.5851(10) 0.9593(18) 0.3222(5) 0.050(3) Uani 1 1 d . . . . .
H18 H 0.659807 1.065379 0.307433 0.060 Uiso 1 1 calc R U . . .
C19 C -0.1752(9) 0.6760(16) 0.1873(4) 0.036(2) Uani 1 1 d . . . . .
H19 H -0.153389 0.789038 0.225322 0.044 Uiso 1 1 calc R U . . .
C20 C 0.1697(11) 0.1258(16) 0.4511(4) 0.044(2) Uani 1 1 d . . . . .
H20 H 0.197740 -0.006868 0.477710 0.053 Uiso 1 1 calc R U . . .
C21 C 0.6189(10) 0.808(2) 0.3755(5) 0.059(3) Uani 1 1 d . . . . .
H21 H 0.716762 0.812563 0.397915 0.071 Uiso 1 1 calc R U . . .
C22 C -0.2936(10) 0.790(2) 0.1381(4) 0.053(2) Uani 1 1 d . . . . .
H22A H -0.312156 0.689157 0.098454 0.080 Uiso 1 1 calc R U . . .
H22B H -0.255248 0.941949 0.123291 0.080 Uiso 1 1 calc R U . . .
H22C H -0.388855 0.813155 0.161241 0.080 Uiso 1 1 calc R U . . .
C23 C 0.1162(9) 0.4064(19) 0.0599(4) 0.048(3) Uani 1 1 d . . . . .
H23A H 0.105018 0.275558 0.027108 0.058 Uiso 1 1 calc R U . . .
H23B H 0.134542 0.551122 0.033937 0.058 Uiso 1 1 calc R U . . .
C24 C 0.4006(10) 0.322(2) 0.0709(4) 0.072(3) Uani 1 1 d . . . . .
H24A H 0.419759 0.459608 0.042861 0.107 Uiso 1 1 calc R U . . .
H24B H 0.389336 0.184009 0.041655 0.107 Uiso 1 1 calc R U . . .
H24C H 0.486332 0.299086 0.103827 0.107 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.459(6) . ?
P1 O2 1.615(5) . ?
P1 C5 1.787(7) . ?
P1 C3 1.796(7) . ?
O2 C11 1.379(8) . ?
C3 C16 1.536(10) . ?
C3 C6 1.535(9) . ?
C3 H3 0.9800 . ?
C4 C11 1.384(10) . ?
C4 C13 1.388(11) . ?
C4 C7 1.461(10) . ?
C5 C10 1.368(11) . ?
C5 C7 1.385(11) . ?
C6 C9 1.509(11) . ?
C6 C19 1.549(10) . ?
C6 H6 0.9800 . ?
C7 C12 1.390(11) . ?
C8 C14 1.359(11) . ?
C8 C11 1.364(10) . ?
C8 H8 0.9300 . ?
C9 C23 1.515(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C18 1.363(11) . ?
C10 H10 0.9300 . ?
C12 C21 1.356(13) . ?
C12 H12 0.9300 . ?
C13 C20 1.361(12) . ?
C13 H13 0.9300 . ?
C14 C20 1.381(12) . ?
C14 H14 0.9300 . ?
C15 C23 1.497(10) . ?
C15 C16 1.501(10) . ?
C15 C24 1.528(10) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C19 1.506(11) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C21 1.354(13) . ?
C18 H18 0.9300 . ?
C19 C22 1.504(11) . ?
C19 H19 0.9800 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O1 P1 O2 111.7(3) . . ?
O1 P1 C5 112.5(4) . . ?
O2 P1 C5 100.6(3) . . ?
O1 P1 C3 114.9(3) . . ?
O2 P1 C3 104.8(3) . . ?
C5 P1 C3 111.2(4) . . ?
C11 O2 P1 121.0(5) . . ?
C16 C3 C6 109.5(6) . . ?
C16 C3 P1 111.4(5) . . ?
C6 C3 P1 112.6(5) . . ?
C16 C3 H3 107.7 . . ?
C6 C3 H3 107.7 . . ?
P1 C3 H3 107.7 . . ?
C11 C4 C13 115.4(7) . . ?
C11 C4 C7 122.0(7) . . ?
C13 C4 C7 122.6(7) . . ?
C10 C5 C7 120.5(7) . . ?
C10 C5 P1 119.8(7) . . ?
C7 C5 P1 119.6(6) . . ?
C9 C6 C3 109.2(6) . . ?
C9 C6 C19 112.8(6) . . ?
C3 C6 C19 114.1(6) . . ?
C9 C6 H6 106.7 . . ?
C3 C6 H6 106.7 . . ?
C19 C6 H6 106.7 . . ?
C5 C7 C12 117.2(7) . . ?
C5 C7 C4 120.4(7) . . ?
C12 C7 C4 122.3(7) . . ?
C14 C8 C11 119.6(8) . . ?
C14 C8 H8 120.2 . . ?
C11 C8 H8 120.2 . . ?
C6 C9 C23 112.1(7) . . ?
C6 C9 H9A 109.2 . . ?
C23 C9 H9A 109.2 . . ?
C6 C9 H9B 109.2 . . ?
C23 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C18 C10 C5 120.9(9) . . ?
C18 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C8 C11 O2 115.9(7) . . ?
C8 C11 C4 123.3(7) . . ?
O2 C11 C4 120.8(7) . . ?
C21 C12 C7 121.1(8) . . ?
C21 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C20 C13 C4 122.1(8) . . ?
C20 C13 H13 118.9 . . ?
C4 C13 H13 118.9 . . ?
C8 C14 C20 119.2(8) . . ?
C8 C14 H14 120.4 . . ?
C20 C14 H14 120.4 . . ?
C23 C15 C16 111.0(7) . . ?
C23 C15 C24 111.0(6) . . ?
C16 C15 C24 112.7(7) . . ?
C23 C15 H15 107.3 . . ?
C16 C15 H15 107.3 . . ?
C24 C15 H15 107.3 . . ?
C15 C16 C3 111.4(7) . . ?
C15 C16 H16A 109.3 . . ?
C3 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C3 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C19 C17 H17A 109.5 . . ?
C19 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C19 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C21 C18 C10 119.2(9) . . ?
C21 C18 H18 120.4 . . ?
C10 C18 H18 120.4 . . ?
C17 C19 C22 110.6(7) . . ?
C17 C19 C6 112.5(7) . . ?
C22 C19 C6 111.8(6) . . ?
C17 C19 H19 107.2 . . ?
C22 C19 H19 107.2 . . ?
C6 C19 H19 107.2 . . ?
C13 C20 C14 120.3(9) . . ?
C13 C20 H20 119.8 . . ?
C14 C20 H20 119.8 . . ?
C12 C21 C18 121.0(8) . . ?
C12 C21 H21 119.5 . . ?
C18 C21 H21 119.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C15 C23 C9 110.3(6) . . ?
C15 C23 H23A 109.6 . . ?
C9 C23 H23A 109.6 . . ?
C15 C23 H23B 109.6 . . ?
C9 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.071



####################################################################### 
# 
# 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_190722f
_database_code_depnum_ccdc_archive 'CCDC 1975583'
loop_
_audit_author_name
_audit_author_address
'XiaoNing Wang'
;Liaocheng University
China
;
_audit_update_record             
;
2020-01-06 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H41 O2 P S'
_chemical_formula_weight         472.64

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   9.9896(9)
_cell_length_b                   29.437(3)
_cell_length_c                   10.1391(12)
_cell_angle_alpha                90
_cell_angle_beta                 115.543(4)
_cell_angle_gamma                90
_cell_volume                     2690.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2487
_cell_measurement_theta_min      2.331
_cell_measurement_theta_max      26.282

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.201
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13397
_diffrn_reflns_av_unetI/netI     0.1636
_diffrn_reflns_av_R_equivalents  0.1132
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.331
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.688
_diffrn_reflns_point_group_measured_fraction_full 0.671
_reflns_number_total             6520
_reflns_number_gt                3142
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.350
_reflns_Friedel_fraction_max     0.365
_reflns_Friedel_fraction_full    0.355

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.2000P)²] 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_abs_structure_details 
;
 Flack x determined using 705 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.31(17)
_chemical_absolute_configuration S
_refine_ls_number_reflns         6520
_refine_ls_number_parameters     591
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.2120
_refine_ls_R_factor_gt           0.1207
_refine_ls_wR_factor_ref         0.3554
_refine_ls_wR_factor_gt          0.3072
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001

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 0.0263(3) 0.24171(11) 0.5094(3) 0.0646(8) Uani 1 1 d . . . . .
P2 P 0.2866(3) 0.41422(12) 0.2721(3) 0.0674(9) Uani 1 1 d . . . . .
S1 S -0.0708(4) 0.28496(13) 0.3329(4) 0.0814(10) Uani 1 1 d . . . . .
S2 S 0.1129(4) 0.36929(13) 0.1758(4) 0.0800(10) Uani 1 1 d . . . . .
O4 O 0.3556(7) 0.4251(3) 0.1776(7) 0.071(2) Uani 1 1 d . . . . .
O1 O -0.0711(7) 0.2303(3) 0.5747(7) 0.069(2) Uani 1 1 d . . . . .
C3 C 0.4275(14) 0.1266(5) 0.7985(13) 0.079(4) Uani 1 1 d . . . . .
H3 H 0.4992 0.1096 0.7853 0.094 Uiso 1 1 calc R U . . .
C4 C 0.4175(12) 0.1736(4) 0.7826(11) 0.059(3) Uani 1 1 d . . . . .
C5 C 0.3067(13) 0.1987(4) 0.7814(11) 0.063(3) Uani 1 1 d . . . . .
C6 C 0.0684(10) 0.4832(4) 0.2005(10) 0.052(3) Uani 1 1 d . . . . .
H6 H -0.0073 0.4598 0.1541 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2059(11) 0.2155(5) 0.3825(12) 0.075(3) Uani 1 1 d . . . . .
H7A H 0.1613 0.2389 0.3094 0.090 Uiso 1 1 calc R U . . .
H7B H 0.2854 0.2295 0.4662 0.090 Uiso 1 1 calc R U . . .
C8 C 0.1046(13) 0.5040(6) 0.0797(13) 0.092(5) Uani 1 1 d . . . . .
H8 H 0.1565 0.4795 0.0554 0.110 Uiso 1 1 calc R U . . .
C9 C 0.2042(13) 0.1794(5) 0.8137(12) 0.078(4) Uani 1 1 d . . . . .
H9 H 0.1286 0.1971 0.8174 0.093 Uiso 1 1 calc R U . . .
C10 C 0.1908(12) 0.2700(4) 0.6377(12) 0.068(3) Uani 1 1 d . . . . .
C11 C 0.3016(12) 0.2482(4) 0.7567(11) 0.065(3) Uani 1 1 d . . . . .
C12 C 0.5336(12) 0.4099(3) 0.5470(12) 0.074(4) Uani 1 1 d D . . . .
O3 O 0.5061(10) 0.4607(3) 0.7611(8) 0.088(3) Uani 1 1 d . . . . .
O2 O 0.5220(10) 0.1969(3) 0.7472(10) 0.094(3) Uani 1 1 d . . . . .
C15 C 0.1990(15) 0.3193(5) 0.6310(15) 0.085(4) Uani 1 1 d . . . . .
H15 H 0.1263 0.3356 0.5554 0.102 Uiso 1 1 calc R U . . .
C16 C 0.4103(12) 0.2748(5) 0.8650(11) 0.074(4) Uani 1 1 d . . . . .
H16 H 0.4795 0.2605 0.9484 0.089 Uiso 1 1 calc R U . . .
C17 C -0.0347(14) 0.1740(4) 0.3019(14) 0.082(4) Uani 1 1 d . . . . .
H17 H -0.0805 0.1965 0.2242 0.098 Uiso 1 1 calc R U . . .
C18 C 0.5494(10) 0.4602(3) 0.5496(10) 0.061(3) Uani 1 1 d D . . . .
C19 C 0.1485(13) 0.4424(5) 0.4401(12) 0.076(4) Uani 1 1 d . . . . .
H19A H 0.0779 0.4180 0.3960 0.091 Uiso 1 1 calc R U . . .
H19B H 0.2332 0.4297 0.5222 0.091 Uiso 1 1 calc R U . . .
C20 C 0.4169(13) 0.3385(3) 0.4408(12) 0.079(4) Uani 1 1 d D . . . .
H20 H 0.3404 0.3224 0.3685 0.095 Uiso 1 1 calc R U . . .
C21 C 0.0782(13) 0.4772(6) 0.4964(14) 0.086(4) Uani 1 1 d . . . . .
H21 H 0.1538 0.5002 0.5483 0.104 Uiso 1 1 calc R U . . .
C22 C 0.2007(13) 0.4599(4) 0.3271(12) 0.065(3) Uani 1 1 d . . . . .
H22 H 0.2766 0.4832 0.3750 0.078 Uiso 1 1 calc R U . . .
C23 C 0.5400(14) 0.4848(4) 0.6632(11) 0.081(4) Uani 1 1 d D . . . .
C24 C 0.563(2) 0.5326(4) 0.6700(13) 0.122(7) Uani 1 1 d D . . . .
H24 H 0.5600 0.5497 0.7458 0.147 Uiso 1 1 calc R U . . .
C25 C 0.2092(15) 0.1319(4) 0.8429(15) 0.086(4) Uani 1 1 d . . . . .
H25 H 0.1375 0.1186 0.8658 0.103 Uiso 1 1 calc R U . . .
C26 C 0.3102(16) 0.3399(5) 0.7327(14) 0.091(4) Uani 1 1 d . . . . .
H26 H 0.3169 0.3712 0.7233 0.110 Uiso 1 1 calc R U . . .
C27 C -0.0464(15) 0.5010(6) 0.3692(13) 0.092(5) Uani 1 1 d . . . . .
H27A H -0.1268 0.4796 0.3213 0.111 Uiso 1 1 calc R U . . .
H27B H -0.0840 0.5257 0.4068 0.111 Uiso 1 1 calc R U . . .
C28 C 0.0875(11) 0.1982(4) 0.4304(11) 0.060(3) Uani 1 1 d . . . . .
H28 H 0.1357 0.1753 0.5065 0.072 Uiso 1 1 calc R U . . .
C29 C 0.5237(16) 0.3157(4) 0.5542(13) 0.097(5) Uani 1 1 d D . . . .
H29 H 0.5256 0.2841 0.5547 0.116 Uiso 1 1 calc R U . . .
C30 C -0.1569(15) 0.1540(5) 0.3330(14) 0.082(4) Uani 1 1 d . . . . .
H30 H -0.1875 0.1771 0.3840 0.098 Uiso 1 1 calc R U . . .
C31 C 0.3183(16) 0.1065(5) 0.8369(15) 0.093(5) Uani 1 1 d . . . . .
H31 H 0.3230 0.0756 0.8579 0.112 Uiso 1 1 calc R U . . .
C32 C 0.5893(12) 0.4816(4) 0.4512(12) 0.085(4) Uani 1 1 d D . . . .
H32 H 0.6033 0.4646 0.3808 0.102 Uiso 1 1 calc R U . . .
C33 C 0.146(2) 0.1504(7) 0.1994(16) 0.120(6) Uani 1 1 d . . . . .
H33A H 0.0995 0.1684 0.1109 0.144 Uiso 1 1 calc R U . . .
H33B H 0.1886 0.1237 0.1765 0.144 Uiso 1 1 calc R U . . .
C34 C 0.4205(11) 0.3863(3) 0.4311(10) 0.062(3) Uani 1 1 d D . . . .
C35 C 0.4182(17) 0.3198(5) 0.8526(14) 0.089(5) Uani 1 1 d . . . . .
H35 H 0.4941 0.3367 0.9229 0.107 Uiso 1 1 calc R U . . .
C36 C 0.6085(15) 0.5273(4) 0.4564(13) 0.106(5) Uani 1 1 d D . . . .
H36 H 0.6348 0.5414 0.3890 0.127 Uiso 1 1 calc R U . . .
C37 C 0.6286(17) 0.3398(4) 0.6681(15) 0.120(6) Uani 1 1 d D . . . .
H37 H 0.6943 0.3243 0.7506 0.144 Uiso 1 1 calc R U . . .
C38 C 0.5893(17) 0.5527(4) 0.5600(14) 0.135(8) Uani 1 1 d D . . . .
H38 H 0.5942 0.5842 0.5564 0.162 Uiso 1 1 calc R U . . .
C39 C 0.0005(14) 0.5189(6) 0.2621(14) 0.093(5) Uani 1 1 d . . . . .
H39A H 0.0727 0.5428 0.3073 0.111 Uiso 1 1 calc R U . . .
H39B H -0.0845 0.5323 0.1822 0.111 Uiso 1 1 calc R U . . .
C40 C 0.0375(16) 0.1367(5) 0.2419(15) 0.097(5) Uani 1 1 d . . . . .
H40A H 0.0804 0.1137 0.3168 0.116 Uiso 1 1 calc R U . . .
H40B H -0.0414 0.1223 0.1585 0.116 Uiso 1 1 calc R U . . .
C41 C 0.026(2) 0.4577(6) 0.6045(15) 0.129(6) Uani 1 1 d . . . . .
H41A H -0.0720 0.4455 0.5526 0.193 Uiso 1 1 calc R U . . .
H41B H 0.0251 0.4812 0.6696 0.193 Uiso 1 1 calc R U . . .
H41C H 0.0925 0.4339 0.6597 0.193 Uiso 1 1 calc R U . . .
C42 C 0.6640(14) 0.1749(5) 0.7810(17) 0.093(5) Uani 1 1 d . . . . .
H42 H 0.6879 0.1529 0.8603 0.111 Uiso 1 1 calc R U . . .
C43 C 0.6388(17) 0.3869(4) 0.6627(13) 0.110(6) Uani 1 1 d D . . . .
H43 H 0.7158 0.4024 0.7365 0.132 Uiso 1 1 calc R U . . .
C44 C 0.6694(19) 0.1548(8) 0.6603(19) 0.138(6) Uani 1 1 d . . . . .
H44A H 0.6606 0.1225 0.6659 0.207 Uiso 1 1 calc R U . . .
H44B H 0.7621 0.1620 0.6581 0.207 Uiso 1 1 calc R U . . .
H44C H 0.5892 0.1660 0.5731 0.207 Uiso 1 1 calc R U . . .
C45 C -0.033(2) 0.5107(8) -0.0572(16) 0.153(9) Uani 1 1 d . . . . .
H45A H -0.1152 0.5151 -0.0339 0.229 Uiso 1 1 calc R U . . .
H45B H -0.0499 0.4843 -0.1182 0.229 Uiso 1 1 calc R U . . .
H45C H -0.0215 0.5369 -0.1079 0.229 Uiso 1 1 calc R U . . .
C47 C 0.2089(19) 0.5407(5) 0.1224(19) 0.118(5) Uani 1 1 d . . . . .
H47A H 0.2458 0.5448 0.0500 0.177 Uiso 1 1 calc R U . . .
H47B H 0.2900 0.5338 0.2149 0.177 Uiso 1 1 calc R U . . .
H47C H 0.1610 0.5680 0.1309 0.177 Uiso 1 1 calc R U . . .
C48 C 0.5940(19) 0.4412(8) 1.0068(17) 0.132(7) Uani 1 1 d . . . . .
H48A H 0.5935 0.4487 1.0988 0.198 Uiso 1 1 calc R U . . .
H48B H 0.6936 0.4346 1.0217 0.198 Uiso 1 1 calc R U . . .
H48C H 0.5325 0.4151 0.9660 0.198 Uiso 1 1 calc R U . . .
C49 C 0.778(2) 0.2177(7) 0.834(3) 0.155(8) Uani 1 1 d . . . . .
H49A H 0.8778 0.2067 0.8859 0.232 Uiso 1 1 calc R U . . .
H49B H 0.7538 0.2370 0.8968 0.232 Uiso 1 1 calc R U . . .
H49C H 0.7702 0.2347 0.7500 0.232 Uiso 1 1 calc R U . . .
C51 C 0.535(2) 0.4808(6) 0.9032(18) 0.127(7) Uani 1 1 d . U . . .
H51 H 0.6097 0.5049 0.9284 0.153 Uiso 1 1 calc R U . . .
C52 C 0.396(2) 0.4990(12) 0.893(3) 0.204(13) Uani 1 1 d . U . . .
H52A H 0.3585 0.5209 0.8160 0.306 Uiso 1 1 calc R U . . .
H52B H 0.4127 0.5132 0.9842 0.306 Uiso 1 1 calc R U . . .
H52C H 0.3259 0.4748 0.8734 0.306 Uiso 1 1 calc R U . . .
C62 C -0.2269(13) 0.3077(4) 0.3575(13) 0.071(3) Uani 1 1 d . . . . .
H62 H -0.2189 0.3003 0.4548 0.085 Uiso 1 1 calc R U . . .
C59 C 0.141(2) 0.3477(4) 0.0258(12) 0.094(5) Uani 1 1 d . . . . .
H59 H 0.2479 0.3454 0.0525 0.113 Uiso 1 1 calc R U . . .
C55 C 0.2745(15) 0.1794(5) 0.3194(15) 0.091(4) Uani 1 1 d . U . . .
H55 H 0.3296 0.1584 0.3998 0.109 Uiso 1 1 calc R U . . .
C56 C 0.3893(14) 0.2000(7) 0.2720(16) 0.144(6) Uani 1 1 d . U . . .
H56A H 0.3412 0.2218 0.1957 0.216 Uiso 1 1 calc R U . . .
H56B H 0.4314 0.1763 0.2367 0.216 Uiso 1 1 calc R U . . .
H56C H 0.4665 0.2147 0.3542 0.216 Uiso 1 1 calc R U . . .
C58 C -0.2934(16) 0.1405(6) 0.1953(16) 0.103(5) Uani 1 1 d . . . . .
H58A H -0.3423 0.1673 0.1429 0.155 Uiso 1 1 calc R U . . .
H58B H -0.3601 0.1235 0.2220 0.155 Uiso 1 1 calc R U . . .
H58C H -0.2636 0.1221 0.1344 0.155 Uiso 1 1 calc R U . . .
C57 C -0.098(3) 0.1104(6) 0.439(2) 0.165(10) Uani 1 1 d . . . . .
H57A H -0.1115 0.0835 0.3816 0.248 Uiso 1 1 calc R U . . .
H57B H -0.1537 0.1076 0.4963 0.248 Uiso 1 1 calc R U . . .
H57C H 0.0050 0.1142 0.5034 0.248 Uiso 1 1 calc R U . . .
C60 C 0.070(3) 0.3006(5) -0.0077(17) 0.181(10) Uani 1 1 d . . . . .
H60A H 0.0090 0.2967 0.0431 0.272 Uiso 1 1 calc R U . . .
H60B H 0.1463 0.2778 0.0239 0.272 Uiso 1 1 calc R U . . .
H60C H 0.0103 0.2977 -0.1110 0.272 Uiso 1 1 calc R U . . .
C61 C 0.067(3) 0.3765(7) -0.1097(17) 0.213(14) Uani 1 1 d . . . . .
H61A H 0.0799 0.3626 -0.1891 0.319 Uiso 1 1 calc R U . . .
H61B H 0.1103 0.4062 -0.0917 0.319 Uiso 1 1 calc R U . . .
H61C H -0.0371 0.3788 -0.1346 0.319 Uiso 1 1 calc R U . . .
C63 C -0.235(2) 0.3574(6) 0.334(3) 0.209(10) Uani 1 1 d . . . . .
H63A H -0.1588 0.3667 0.3063 0.313 Uiso 1 1 calc R U . . .
H63B H -0.2212 0.3725 0.4231 0.313 Uiso 1 1 calc R U . . .
H63C H -0.3304 0.3652 0.2583 0.313 Uiso 1 1 calc R U . . .
C64 C -0.355(2) 0.2871(15) 0.247(4) 0.29(2) Uani 1 1 d . . . . .
H64A H -0.3462 0.2871 0.1560 0.435 Uiso 1 1 calc R U . . .
H64B H -0.4417 0.3039 0.2352 0.435 Uiso 1 1 calc R U . . .
H64C H -0.3632 0.2564 0.2740 0.435 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.434(8) . ?
P1 C28 1.754(12) . ?
P1 C10 1.800(12) . ?
P1 S1 2.066(4) . ?
P2 O4 1.437(8) . ?
P2 C34 1.790(9) . ?
P2 C22 1.809(13) . ?
P2 S2 2.062(5) . ?
S1 C62 1.810(13) . ?
S2 C59 1.781(15) . ?
C3 C4 1.391(18) . ?
C3 C31 1.43(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.327(16) . ?
C4 O2 1.419(14) . ?
C5 C9 1.329(17) . ?
C5 C11 1.475(16) . ?
C6 C39 1.523(18) . ?
C6 C22 1.549(14) . ?
C6 C8 1.546(17) . ?
C6 H6 0.9800 . ?
C7 C55 1.544(19) . ?
C7 C28 1.545(15) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C47 1.43(2) . ?
C8 C45 1.484(19) . ?
C8 H8 0.9800 . ?
C9 C25 1.426(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(15) . ?
C10 C15 1.457(18) . ?
C11 C16 1.403(15) . ?
C12 C43 1.371(13) . ?
C12 C34 1.413(12) . ?
C12 C18 1.488(14) . ?
O3 C23 1.375(14) . ?
O3 C51 1.467(19) . ?
O2 C42 1.459(16) . ?
C15 C26 1.295(17) . ?
C15 H15 0.9300 . ?
C16 C35 1.337(19) . ?
C16 H16 0.9300 . ?
C17 C30 1.51(2) . ?
C17 C28 1.525(15) . ?
C17 C40 1.572(19) . ?
C17 H17 0.9800 . ?
C18 C32 1.376(13) . ?
C18 C23 1.397(13) . ?
C19 C21 1.488(19) . ?
C19 C22 1.538(17) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C29 1.362(13) . ?
C20 C34 1.412(12) . ?
C20 H20 0.9300 . ?
C21 C41 1.51(2) . ?
C21 C27 1.522(18) . ?
C21 H21 0.9800 . ?
C22 H22 0.9800 . ?
C23 C24 1.422(14) . ?
C24 C38 1.387(16) . ?
C24 H24 0.9300 . ?
C25 C31 1.34(2) . ?
C25 H25 0.9300 . ?
C26 C35 1.364(18) . ?
C26 H26 0.9300 . ?
C27 C39 1.45(2) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28 0.9800 . ?
C29 C37 1.375(14) . ?
C29 H29 0.9300 . ?
C30 C58 1.524(18) . ?
C30 C57 1.61(2) . ?
C30 H30 0.9800 . ?
C31 H31 0.9300 . ?
C32 C36 1.356(14) . ?
C32 H32 0.9300 . ?
C33 C40 1.39(2) . ?
C33 C55 1.58(2) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C35 H35 0.9300 . ?
C36 C38 1.369(16) . ?
C36 H36 0.9300 . ?
C37 C43 1.393(14) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 C44 1.38(2) . ?
C42 C49 1.63(2) . ?
C42 H42 0.9800 . ?
C43 H43 0.9300 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 C51 1.51(3) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C51 C52 1.45(3) . ?
C51 H51 0.9800 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C62 C64 1.42(3) . ?
C62 C63 1.48(2) . ?
C62 H62 0.9800 . ?
C59 C61 1.51(2) . ?
C59 C60 1.53(2) . ?
C59 H59 0.9800 . ?
C55 C56 1.55(2) . ?
C55 H55 0.9800 . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
C63 H63A 0.9600 . ?
C63 H63B 0.9600 . ?
C63 H63C 0.9600 . ?
C64 H64A 0.9600 . ?
C64 H64B 0.9600 . ?
C64 H64C 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
O1 P1 C28 118.6(5) . . ?
O1 P1 C10 111.4(5) . . ?
C28 P1 C10 106.2(5) . . ?
O1 P1 S1 112.7(3) . . ?
C28 P1 S1 100.4(4) . . ?
C10 P1 S1 106.4(4) . . ?
O4 P2 C34 108.5(5) . . ?
O4 P2 C22 117.8(6) . . ?
C34 P2 C22 109.5(5) . . ?
O4 P2 S2 112.1(3) . . ?
C34 P2 S2 106.3(4) . . ?
C22 P2 S2 102.0(4) . . ?
C62 S1 P1 102.7(4) . . ?
C59 S2 P2 102.7(6) . . ?
C4 C3 C31 114.6(12) . . ?
C4 C3 H3 122.7 . . ?
C31 C3 H3 122.7 . . ?
C5 C4 C3 125.0(11) . . ?
C5 C4 O2 115.4(10) . . ?
C3 C4 O2 119.2(11) . . ?
C9 C5 C4 119.2(11) . . ?
C9 C5 C11 119.3(12) . . ?
C4 C5 C11 121.3(11) . . ?
C39 C6 C22 109.7(9) . . ?
C39 C6 C8 110.4(11) . . ?
C22 C6 C8 115.1(9) . . ?
C39 C6 H6 107.1 . . ?
C22 C6 H6 107.1 . . ?
C8 C6 H6 107.1 . . ?
C55 C7 C28 116.1(11) . . ?
C55 C7 H7A 108.3 . . ?
C28 C7 H7A 108.3 . . ?
C55 C7 H7B 108.3 . . ?
C28 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C47 C8 C45 116.2(16) . . ?
C47 C8 C6 116.6(12) . . ?
C45 C8 C6 110.8(13) . . ?
C47 C8 H8 103.7 . . ?
C45 C8 H8 103.7 . . ?
C6 C8 H8 103.7 . . ?
C5 C9 C25 120.5(12) . . ?
C5 C9 H9 119.7 . . ?
C25 C9 H9 119.7 . . ?
C11 C10 C15 117.4(10) . . ?
C11 C10 P1 123.3(9) . . ?
C15 C10 P1 118.6(8) . . ?
C10 C11 C16 118.6(11) . . ?
C10 C11 C5 123.9(10) . . ?
C16 C11 C5 117.4(10) . . ?
C43 C12 C34 120.8(9) . . ?
C43 C12 C18 116.2(9) . . ?
C34 C12 C18 123.0(8) . . ?
C23 O3 C51 119.8(11) . . ?
C4 O2 C42 118.2(10) . . ?
C26 C15 C10 118.4(12) . . ?
C26 C15 H15 120.8 . . ?
C10 C15 H15 120.8 . . ?
C35 C16 C11 122.5(11) . . ?
C35 C16 H16 118.8 . . ?
C11 C16 H16 118.8 . . ?
C30 C17 C28 115.3(11) . . ?
C30 C17 C40 110.9(11) . . ?
C28 C17 C40 109.0(10) . . ?
C30 C17 H17 107.1 . . ?
C28 C17 H17 107.1 . . ?
C40 C17 H17 107.1 . . ?
C32 C18 C23 120.3(10) . . ?
C32 C18 C12 120.3(10) . . ?
C23 C18 C12 119.0(9) . . ?
C21 C19 C22 115.0(12) . . ?
C21 C19 H19A 108.5 . . ?
C22 C19 H19A 108.5 . . ?
C21 C19 H19B 108.5 . . ?
C22 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C29 C20 C34 121.1(10) . . ?
C29 C20 H20 119.5 . . ?
C34 C20 H20 119.5 . . ?
C19 C21 C41 112.4(13) . . ?
C19 C21 C27 109.9(10) . . ?
C41 C21 C27 112.2(12) . . ?
C19 C21 H21 107.4 . . ?
C41 C21 H21 107.4 . . ?
C27 C21 H21 107.4 . . ?
C19 C22 C6 108.8(9) . . ?
C19 C22 P2 109.8(8) . . ?
C6 C22 P2 115.0(7) . . ?
C19 C22 H22 107.7 . . ?
C6 C22 H22 107.7 . . ?
P2 C22 H22 107.7 . . ?
O3 C23 C18 117.0(9) . . ?
O3 C23 C24 123.9(11) . . ?
C18 C23 C24 119.1(11) . . ?
C38 C24 C23 117.8(11) . . ?
C38 C24 H24 121.1 . . ?
C23 C24 H24 121.1 . . ?
C31 C25 C9 119.5(13) . . ?
C31 C25 H25 120.2 . . ?
C9 C25 H25 120.2 . . ?
C15 C26 C35 125.7(13) . . ?
C15 C26 H26 117.2 . . ?
C35 C26 H26 117.2 . . ?
C39 C27 C21 113.0(12) . . ?
C39 C27 H27A 109.0 . . ?
C21 C27 H27A 109.0 . . ?
C39 C27 H27B 109.0 . . ?
C21 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C17 C28 C7 108.9(9) . . ?
C17 C28 P1 115.0(8) . . ?
C7 C28 P1 111.6(9) . . ?
C17 C28 H28 107.0 . . ?
C7 C28 H28 107.0 . . ?
P1 C28 H28 107.0 . . ?
C20 C29 C37 119.4(10) . . ?
C20 C29 H29 120.3 . . ?
C37 C29 H29 120.3 . . ?
C17 C30 C58 113.4(11) . . ?
C17 C30 C57 111.0(14) . . ?
C58 C30 C57 109.1(13) . . ?
C17 C30 H30 107.7 . . ?
C58 C30 H30 107.7 . . ?
C57 C30 H30 107.7 . . ?
C25 C31 C3 120.6(13) . . ?
C25 C31 H31 119.7 . . ?
C3 C31 H31 119.7 . . ?
C36 C32 C18 120.4(11) . . ?
C36 C32 H32 119.8 . . ?
C18 C32 H32 119.8 . . ?
C40 C33 C55 113.7(13) . . ?
C40 C33 H33A 108.8 . . ?
C55 C33 H33A 108.8 . . ?
C40 C33 H33B 108.8 . . ?
C55 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C20 C34 C12 117.9(8) . . ?
C20 C34 P2 119.3(7) . . ?
C12 C34 P2 122.8(7) . . ?
C16 C35 C26 117.3(12) . . ?
C16 C35 H35 121.4 . . ?
C26 C35 H35 121.4 . . ?
C32 C36 C38 120.6(12) . . ?
C32 C36 H36 119.7 . . ?
C38 C36 H36 119.7 . . ?
C29 C37 C43 121.5(11) . . ?
C29 C37 H37 119.3 . . ?
C43 C37 H37 119.3 . . ?
C36 C38 C24 121.4(12) . . ?
C36 C38 H38 119.3 . . ?
C24 C38 H38 119.3 . . ?
C27 C39 C6 113.5(13) . . ?
C27 C39 H39A 108.9 . . ?
C6 C39 H39A 108.9 . . ?
C27 C39 H39B 108.9 . . ?
C6 C39 H39B 108.9 . . ?
H39A C39 H39B 107.7 . . ?
C33 C40 C17 117.8(15) . . ?
C33 C40 H40A 107.9 . . ?
C17 C40 H40A 107.9 . . ?
C33 C40 H40B 107.9 . . ?
C17 C40 H40B 107.9 . . ?
H40A C40 H40B 107.2 . . ?
C21 C41 H41A 109.5 . . ?
C21 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C21 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C44 C42 O2 112.8(12) . . ?
C44 C42 C49 109.5(16) . . ?
O2 C42 C49 101.9(12) . . ?
C44 C42 H42 110.8 . . ?
O2 C42 H42 110.8 . . ?
C49 C42 H42 110.8 . . ?
C12 C43 C37 119.0(11) . . ?
C12 C43 H43 120.5 . . ?
C37 C43 H43 120.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C8 C45 H45A 109.5 . . ?
C8 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C8 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C8 C47 H47A 109.5 . . ?
C8 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C8 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C51 C48 H48A 109.5 . . ?
C51 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C51 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C42 C49 H49A 109.5 . . ?
C42 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C42 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C52 C51 O3 107.8(16) . . ?
C52 C51 C48 114(2) . . ?
O3 C51 C48 102.9(14) . . ?
C52 C51 H51 110.6 . . ?
O3 C51 H51 110.6 . . ?
C48 C51 H51 110.6 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C64 C62 C63 109(2) . . ?
C64 C62 S1 105.5(17) . . ?
C63 C62 S1 109.6(11) . . ?
C64 C62 H62 110.8 . . ?
C63 C62 H62 110.8 . . ?
S1 C62 H62 110.8 . . ?
C61 C59 C60 107.9(13) . . ?
C61 C59 S2 112.3(14) . . ?
C60 C59 S2 106.4(13) . . ?
C61 C59 H59 110.1 . . ?
C60 C59 H59 110.1 . . ?
S2 C59 H59 110.1 . . ?
C7 C55 C56 112.3(13) . . ?
C7 C55 C33 109.2(11) . . ?
C56 C55 C33 115.9(12) . . ?
C7 C55 H55 106.2 . . ?
C56 C55 H55 106.2 . . ?
C33 C55 H55 106.2 . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C30 C58 H58A 109.5 . . ?
C30 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C30 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C30 C57 H57A 109.5 . . ?
C30 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C30 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C59 C60 H60A 109.5 . . ?
C59 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C59 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C59 C61 H61A 109.5 . . ?
C59 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
C59 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C62 C63 H63A 109.5 . . ?
C62 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C62 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C62 C64 H64A 109.5 . . ?
C62 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C62 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C62 H62 O1 0.98 2.52 3.084(14) 116.4 .
C20 H20 S2 0.93 2.66 3.198(11) 117.7 .
C19 H19A S2 0.97 2.80 3.334(13) 115.5 .
C17 H17 S1 0.98 2.81 3.317(12) 112.8 .
C15 H15 S1 0.93 2.71 3.225(13) 115.6 .
C7 H7A S1 0.97 2.78 3.299(12) 114.0 .
C6 H6 S2 0.98 2.89 3.405(11) 113.7 .
C6 H6 S2 0.98 2.89 3.405(11) 113.7 .
C7 H7A S1 0.97 2.78 3.299(12) 114.0 .
C15 H15 S1 0.93 2.71 3.225(13) 115.6 .
C17 H17 S1 0.98 2.81 3.317(12) 112.8 .
C19 H19A S2 0.97 2.80 3.334(13) 115.5 .
C20 H20 S2 0.93 2.66 3.198(11) 117.7 .
C62 H62 O1 0.98 2.52 3.084(14) 116.4 .
C6 H6 S2 0.98 2.89 3.405(11) 113.7 .
C7 H7A S1 0.97 2.78 3.299(12) 114.0 .
C15 H15 S1 0.93 2.71 3.225(13) 115.6 .
C17 H17 S1 0.98 2.81 3.317(12) 112.8 .
C19 H19A S2 0.97 2.80 3.334(13) 115.5 .
C20 H20 S2 0.93 2.66 3.198(11) 117.7 .
C62 H62 O1 0.98 2.52 3.084(14) 116.4 .

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.097

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_191220b
_database_code_depnum_ccdc_archive 'CCDC 1975584'
loop_
_audit_author_name
_audit_author_address
'Xiao Ning Wang Xiao Ning Wang'
;Liaocheng University
China
;
_audit_update_record             
;
2020-03-18 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H27 O2 P'
_chemical_formula_weight         354.40

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'

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

_cell_length_a                   18.9435(18)
_cell_length_b                   18.9435(18)
_cell_length_c                   10.5234(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3776.4(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3154
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.143

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18525
_diffrn_reflns_av_unetI/netI     0.1214
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.150
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             6614
_reflns_number_gt                3079
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.959

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1506P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.18(12)
_chemical_absolute_configuration S
_refine_ls_number_reflns         6614
_refine_ls_number_parameters     511
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1633
_refine_ls_R_factor_gt           0.0880
_refine_ls_wR_factor_ref         0.2591
_refine_ls_wR_factor_gt          0.2098
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.001

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
O1 O 0.2398(4) 0.7973(4) 0.1571(8) 0.076(2) Uani 1 1 d . . . . .
O2 O 0.7580(3) 0.2582(4) 0.1555(8) 0.071(2) Uani 1 1 d . . . . .
O3 O 0.7226(4) 0.1599(3) 0.0086(7) 0.063(2) Uani 1 1 d . . . . .
O4 O 0.2274(4) 0.6926(4) 0.0141(7) 0.062(2) Uani 1 1 d . . . . .
P1 P 0.69890(15) 0.21366(14) 0.1175(3) 0.0624(8) Uani 1 1 d . . . . .
P2 P 0.19185(14) 0.74035(14) 0.1196(3) 0.0636(8) Uani 1 1 d . . . . .
C3 C 0.6709(6) 0.1550(5) 0.2342(11) 0.060(3) Uani 1 1 d . . . . .
C4 C 0.6385(5) 0.0912(5) 0.1971(12) 0.060(3) Uani 1 1 d . . . . .
C5 C 0.6145(6) 0.0443(6) 0.2896(13) 0.070(3) Uani 1 1 d . . . . .
H5 H 0.5934 0.0019 0.2663 0.05(3) Uiso 1 1 calc R . . . .
C6 C 0.6769(6) 0.1056(6) -0.0257(11) 0.062(3) Uani 1 1 d . . . . .
C7 C 0.6344(6) 0.0728(6) 0.0614(11) 0.063(3) Uani 1 1 d . . . . .
C8 C 0.6804(6) 0.1683(6) 0.3631(13) 0.071(3) Uani 1 1 d . . . . .
H8 H 0.7027 0.2098 0.3879 0.17(8) Uiso 1 1 calc R . . . .
C9 C 0.6261(5) 0.2598(5) 0.0533(12) 0.060(3) Uani 1 1 d . . . . .
H9 H 0.5846 0.2294 0.0628 0.10(5) Uiso 1 1 calc R . . . .
C10 C 0.6364(7) 0.2733(8) -0.0916(13) 0.079(4) Uani 1 1 d . . . . .
H10A H 0.6777 0.3028 -0.1038 0.13(6) Uiso 1 1 calc R . . . .
H10B H 0.6451 0.2286 -0.1337 0.28(13) Uiso 1 1 calc R . . . .
C11 C 0.5931(7) 0.0188(6) 0.0163(14) 0.077(4) Uani 1 1 d . . . . .
H11 H 0.5634 -0.0049 0.0722 0.10(5) Uiso 1 1 calc R . . . .
C12 C 0.6820(7) 0.0851(7) -0.1527(12) 0.076(4) Uani 1 1 d . . . . .
H12 H 0.7128 0.1075 -0.2085 0.10(5) Uiso 1 1 calc R . . . .
C13 C 0.6393(8) 0.0301(7) -0.1919(16) 0.086(4) Uani 1 1 d . . . . .
H13 H 0.6413 0.0145 -0.2756 0.26(12) Uiso 1 1 calc R . . . .
C14 C 0.6225(7) 0.0617(7) 0.4162(14) 0.075(3) Uani 1 1 d . . . . .
H14 H 0.6034 0.0317 0.4772 0.27(13) Uiso 1 1 calc R . . . .
C15 C 0.5944(8) -0.0011(7) -0.1083(15) 0.092(4) Uani 1 1 d . . . . .
H15 H 0.5641 -0.0365 -0.1364 0.13(5) Uiso 1 1 calc R . . . .
C16 C 0.6089(6) 0.3297(6) 0.1170(13) 0.070(3) Uani 1 1 d . . . . .
H16 H 0.6491 0.3608 0.0993 0.40(19) Uiso 1 1 calc R . . . .
C17 C 0.5568(8) 0.3738(7) -0.0887(15) 0.091(4) Uani 1 1 d . . . . .
H17A H 0.5145 0.3937 -0.1265 0.16(7) Uiso 1 1 calc R . . . .
H17B H 0.5950 0.4072 -0.1016 0.10(5) Uiso 1 1 calc R . . . .
C18 C 0.5899(10) 0.3187(10) -0.2967(15) 0.118(6) Uani 1 1 d . . . . .
H18A H 0.5478 0.3341 -0.3394 0.17(8) Uiso 1 1 calc R . . . .
H18B H 0.6054 0.2748 -0.3327 1.3(9) Uiso 1 1 calc R . . . .
H18C H 0.6262 0.3535 -0.3069 0.07(4) Uiso 1 1 calc R . . . .
C19 C 0.6572(6) 0.1213(7) 0.4564(14) 0.073(3) Uani 1 1 d . . . . .
H19 H 0.6651 0.1299 0.5422 0.17(8) Uiso 1 1 calc R . . . .
C20 C 0.5391(8) 0.2842(8) 0.3070(17) 0.098(5) Uani 1 1 d . . . . .
H20A H 0.4967 0.3061 0.2767 0.28(14) Uiso 1 1 calc R . . . .
H20B H 0.5384 0.2827 0.3982 0.18(9) Uiso 1 1 calc R . . . .
H20C H 0.5422 0.2370 0.2742 0.10(4) Uiso 1 1 calc R . . . .
C21 C 0.6027(7) 0.3265(6) 0.2626(14) 0.079(4) Uani 1 1 d . . . . .
H21 H 0.6451 0.3029 0.2950 0.5(3) Uiso 1 1 calc R . . . .
C22 C 0.6003(10) 0.4002(7) 0.321(2) 0.113(6) Uani 1 1 d . . . . .
H22A H 0.6403 0.4269 0.2925 0.25(12) Uiso 1 1 calc R . . . .
H22B H 0.6013 0.3965 0.4119 0.27(15) Uiso 1 1 calc R . . . .
H22C H 0.5576 0.4236 0.2952 0.12(6) Uiso 1 1 calc R . . . .
C23 C 0.5450(8) 0.3641(8) 0.0521(16) 0.094(4) Uani 1 1 d . . . . .
H23A H 0.5037 0.3348 0.0653 0.31(16) Uiso 1 1 calc R . . . .
H23B H 0.5360 0.4097 0.0908 1.0(6) Uiso 1 1 calc R . . . .
C24 C 0.5740(7) 0.3083(7) -0.1528(15) 0.087(4) Uani 1 1 d . . . . .
H24 H 0.5334 0.2765 -0.1449 0.11(5) Uiso 1 1 calc R . . . .
C27 C 0.1618(5) 0.6071(6) 0.2040(13) 0.065(3) Uani 1 1 d . . . . .
C28 C 0.1964(6) 0.6294(6) -0.0211(12) 0.065(3) Uani 1 1 d . . . . .
C29 C 0.1638(6) 0.5860(5) 0.0680(11) 0.060(3) Uani 1 1 d . . . . .
C30 C 0.1764(5) 0.6764(6) 0.2352(11) 0.058(3) Uani 1 1 d . . . . .
C31 C 0.0757(6) 0.8318(6) 0.1119(12) 0.066(3) Uani 1 1 d . . . . .
H31 H 0.1049 0.8724 0.0883 0.16(7) Uiso 1 1 calc R . . . .
C32 C 0.1470(6) 0.5570(6) 0.2944(12) 0.070(3) Uani 1 1 d . . . . .
H32 H 0.1359 0.5110 0.2711 0.05(3) Uiso 1 1 calc R . . . .
C33 C 0.0467(7) 0.7943(7) -0.1533(13) 0.077(3) Uani 1 1 d . . . . .
H33 H 0.0175 0.7519 -0.1444 0.11(5) Uiso 1 1 calc R . . . .
C34 C 0.2028(6) 0.6105(7) -0.1497(12) 0.075(3) Uani 1 1 d . . . . .
H34 H 0.2249 0.6400 -0.2081 0.06(3) Uiso 1 1 calc R . . . .
C35 C 0.0090(8) 0.8543(8) -0.0913(14) 0.094(4) Uani 1 1 d . . . . .
H35A H -0.0379 0.8589 -0.1273 0.10(4) Uiso 1 1 calc R . . . .
H35B H 0.0344 0.8979 -0.1073 0.07(3) Uiso 1 1 calc R . . . .
C36 C 0.1174(6) 0.7799(7) -0.0914(11) 0.070(3) Uani 1 1 d . . . . .
H36A H 0.1484 0.8199 -0.1049 0.06(3) Uiso 1 1 calc R . . . .
H36B H 0.1389 0.7389 -0.1307 0.15(6) Uiso 1 1 calc R . . . .
C37 C 0.1490(6) 0.5765(7) 0.4205(14) 0.074(3) Uani 1 1 d . . . . .
H37 H 0.1391 0.5427 0.4822 0.13(6) Uiso 1 1 calc R . . . .
C38 C 0.1093(6) 0.7667(6) 0.0526(11) 0.061(3) Uani 1 1 d . . . . .
H38 H 0.0762 0.7274 0.0634 0.16(7) Uiso 1 1 calc R . . . .
C39 C 0.0718(7) 0.8301(6) 0.2614(12) 0.073(3) Uani 1 1 d . . . . .
H39 H 0.1185 0.8154 0.2914 0.18(8) Uiso 1 1 calc R . . . .
C40 C 0.1785(6) 0.6919(7) 0.3676(13) 0.075(3) Uani 1 1 d . . . . .
H40 H 0.1898 0.7376 0.3931 0.08(4) Uiso 1 1 calc R . . . .
C41 C 0.1367(7) 0.5235(6) 0.0225(15) 0.080(4) Uani 1 1 d . . . . .
H41 H 0.1144 0.4930 0.0790 0.09(4) Uiso 1 1 calc R . . . .
C42 C 0.1415(8) 0.5044(8) -0.1030(16) 0.089(4) Uani 1 1 d . . . . .
H42 H 0.1214 0.4624 -0.1311 0.17(8) Uiso 1 1 calc R . . . .
C43 C 0.0202(8) 0.7783(7) 0.3141(18) 0.102(5) Uani 1 1 d . . . . .
H43A H 0.0235 0.7779 0.4051 0.18(9) Uiso 1 1 calc R . . . .
H43B H 0.0307 0.7320 0.2818 0.09(4) Uiso 1 1 calc R . . . .
H43C H -0.0267 0.7915 0.2893 0.10(5) Uiso 1 1 calc R . . . .
C44 C 0.0560(10) 0.8095(9) -0.2955(15) 0.104(5) Uani 1 1 d . . . . .
H44A H 0.0105 0.8163 -0.3339 0.27(13) Uiso 1 1 calc R . . . .
H44B H 0.0793 0.7703 -0.3353 0.10(5) Uiso 1 1 calc R . . . .
H44C H 0.0839 0.8513 -0.3063 0.31(17) Uiso 1 1 calc R . . . .
C45 C 0.1647(6) 0.6430(7) 0.4576(15) 0.075(3) Uani 1 1 d . . . . .
H45 H 0.1661 0.6548 0.5434 0.12(6) Uiso 1 1 calc R . . . .
C46 C 0.1753(8) 0.5469(8) -0.1848(17) 0.091(4) Uani 1 1 d . . . . .
H46 H 0.1802 0.5324 -0.2688 0.13(6) Uiso 1 1 calc R . . . .
C47 C 0.0036(7) 0.8421(9) 0.0495(14) 0.093(4) Uani 1 1 d . . . . .
H47A H -0.0199 0.8822 0.0884 0.5(3) Uiso 1 1 calc R . . . .
H47B H -0.0252 0.8006 0.0648 0.09(4) Uiso 1 1 calc R . . . .
C48 C 0.0595(11) 0.9028(8) 0.3126(18) 0.110(6) Uani 1 1 d . . . . .
H48A H 0.0146 0.9199 0.2835 0.12(7) Uiso 1 1 calc R . . . .
H48B H 0.0962 0.9338 0.2832 0.18(9) Uiso 1 1 calc R . . . .
H48C H 0.0598 0.9014 0.4038 0.4(2) 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
O1 P2 1.464(7) . ?
O2 P1 1.458(7) . ?
O3 C6 1.391(12) . ?
O3 P1 1.598(7) . ?
O4 C28 1.383(12) . ?
O4 P2 1.583(7) . ?
P1 C3 1.739(11) . ?
P1 C9 1.768(10) . ?
P2 C30 1.741(11) . ?
P2 C38 1.787(11) . ?
C3 C8 1.392(16) . ?
C3 C4 1.411(14) . ?
C4 C5 1.394(15) . ?
C4 C7 1.472(15) . ?
C5 C14 1.382(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(15) . ?
C6 C12 1.395(16) . ?
C7 C11 1.373(15) . ?
C8 C19 1.396(16) . ?
C8 H8 0.9300 . ?
C9 C16 1.518(15) . ?
C9 C10 1.559(17) . ?
C9 H9 0.9800 . ?
C10 C24 1.500(16) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C15 1.365(18) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(18) . ?
C12 H12 0.9300 . ?
C13 C15 1.360(19) . ?
C13 H13 0.9300 . ?
C14 C19 1.373(17) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.538(19) . ?
C16 C23 1.535(17) . ?
C16 H16 0.9800 . ?
C17 C24 1.449(18) . ?
C17 C23 1.510(19) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C24 1.56(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C20 C21 1.520(17) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.526(17) . ?
C21 H21 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24 0.9800 . ?
C27 C32 1.372(16) . ?
C27 C30 1.383(14) . ?
C27 C29 1.487(16) . ?
C28 C29 1.391(16) . ?
C28 C34 1.405(16) . ?
C29 C41 1.377(15) . ?
C30 C40 1.424(16) . ?
C31 C47 1.529(16) . ?
C31 C38 1.522(15) . ?
C31 C39 1.575(17) . ?
C31 H31 0.9800 . ?
C32 C37 1.377(17) . ?
C32 H32 0.9300 . ?
C33 C35 1.493(17) . ?
C33 C36 1.514(15) . ?
C33 C44 1.534(19) . ?
C33 H33 0.9800 . ?
C34 C46 1.364(17) . ?
C34 H34 0.9300 . ?
C35 C47 1.503(18) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C38 1.543(15) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C45 1.353(17) . ?
C37 H37 0.9300 . ?
C38 H38 0.9800 . ?
C39 C43 1.492(17) . ?
C39 C48 1.498(17) . ?
C39 H39 0.9800 . ?
C40 C45 1.351(16) . ?
C40 H40 0.9300 . ?
C41 C42 1.373(19) . ?
C41 H41 0.9300 . ?
C42 C46 1.342(19) . ?
C42 H42 0.9300 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 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
C6 O3 P1 118.9(6) . . ?
C28 O4 P2 120.0(7) . . ?
O2 P1 O3 110.5(4) . . ?
O2 P1 C3 114.3(5) . . ?
O3 P1 C3 100.6(5) . . ?
O2 P1 C9 114.6(5) . . ?
O3 P1 C9 105.1(5) . . ?
C3 P1 C9 110.4(5) . . ?
O1 P2 O4 110.2(4) . . ?
O1 P2 C30 115.4(5) . . ?
O4 P2 C30 99.5(5) . . ?
O1 P2 C38 116.3(5) . . ?
O4 P2 C38 104.8(5) . . ?
C30 P2 C38 108.8(5) . . ?
C8 C3 C4 118.8(10) . . ?
C8 C3 P1 122.2(8) . . ?
C4 C3 P1 119.0(9) . . ?
C5 C4 C3 119.7(12) . . ?
C5 C4 C7 120.6(10) . . ?
C3 C4 C7 119.6(10) . . ?
C14 C5 C4 119.1(12) . . ?
C14 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C7 C6 O3 121.8(11) . . ?
C7 C6 C12 123.7(11) . . ?
O3 C6 C12 114.3(11) . . ?
C6 C7 C11 116.2(12) . . ?
C6 C7 C4 120.7(11) . . ?
C11 C7 C4 122.8(11) . . ?
C19 C8 C3 121.9(12) . . ?
C19 C8 H8 119.0 . . ?
C3 C8 H8 119.0 . . ?
C16 C9 C10 108.4(10) . . ?
C16 C9 P1 115.4(8) . . ?
C10 C9 P1 110.9(8) . . ?
C16 C9 H9 107.2 . . ?
C10 C9 H9 107.2 . . ?
P1 C9 H9 107.2 . . ?
C24 C10 C9 113.2(11) . . ?
C24 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C24 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C15 C11 C7 121.9(13) . . ?
C15 C11 H11 119.1 . . ?
C7 C11 H11 119.1 . . ?
C13 C12 C6 117.1(13) . . ?
C13 C12 H12 121.4 . . ?
C6 C12 H12 121.4 . . ?
C15 C13 C12 120.1(15) . . ?
C15 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C19 C14 C5 123.1(13) . . ?
C19 C14 H14 118.5 . . ?
C5 C14 H14 118.5 . . ?
C13 C15 C11 120.9(14) . . ?
C13 C15 H15 119.6 . . ?
C11 C15 H15 119.6 . . ?
C9 C16 C21 115.0(10) . . ?
C9 C16 C23 110.0(11) . . ?
C21 C16 C23 113.5(11) . . ?
C9 C16 H16 105.8 . . ?
C21 C16 H16 105.8 . . ?
C23 C16 H16 105.8 . . ?
C24 C17 C23 112.7(13) . . ?
C24 C17 H17A 109.1 . . ?
C23 C17 H17A 109.1 . . ?
C24 C17 H17B 109.1 . . ?
C23 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C24 C18 H18A 109.5 . . ?
C24 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C24 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 C8 117.3(14) . . ?
C14 C19 H19 121.3 . . ?
C8 C19 H19 121.3 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C20 C21 C22 109.6(12) . . ?
C20 C21 C16 112.8(12) . . ?
C22 C21 C16 111.6(13) . . ?
C20 C21 H21 107.5 . . ?
C22 C21 H21 107.6 . . ?
C16 C21 H21 107.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 C16 111.8(12) . . ?
C17 C23 H23A 109.3 . . ?
C16 C23 H23A 109.3 . . ?
C17 C23 H23B 109.3 . . ?
C16 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
C17 C24 C10 110.9(13) . . ?
C17 C24 C18 112.8(13) . . ?
C10 C24 C18 108.7(12) . . ?
C17 C24 H24 108.1 . . ?
C10 C24 H24 108.1 . . ?
C18 C24 H24 108.1 . . ?
C32 C27 C30 122.2(12) . . ?
C32 C27 C29 119.2(10) . . ?
C30 C27 C29 118.6(11) . . ?
O4 C28 C29 121.3(11) . . ?
O4 C28 C34 116.2(11) . . ?
C29 C28 C34 122.4(11) . . ?
C41 C29 C28 116.1(12) . . ?
C41 C29 C27 123.7(11) . . ?
C28 C29 C27 120.1(10) . . ?
C27 C30 C40 115.7(11) . . ?
C27 C30 P2 121.9(9) . . ?
C40 C30 P2 122.4(9) . . ?
C47 C31 C38 107.5(10) . . ?
C47 C31 C39 113.0(10) . . ?
C38 C31 C39 114.4(10) . . ?
C47 C31 H31 107.2 . . ?
C38 C31 H31 107.2 . . ?
C39 C31 H31 107.2 . . ?
C37 C32 C27 118.5(12) . . ?
C37 C32 H32 120.7 . . ?
C27 C32 H32 120.7 . . ?
C35 C33 C36 111.8(11) . . ?
C35 C33 C44 109.8(12) . . ?
C36 C33 C44 110.7(12) . . ?
C35 C33 H33 108.2 . . ?
C36 C33 H33 108.2 . . ?
C44 C33 H33 108.2 . . ?
C46 C34 C28 117.0(13) . . ?
C46 C34 H34 121.5 . . ?
C28 C34 H34 121.5 . . ?
C33 C35 C47 110.3(13) . . ?
C33 C35 H35A 109.6 . . ?
C47 C35 H35A 109.6 . . ?
C33 C35 H35B 109.6 . . ?
C47 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
C33 C36 C38 111.4(10) . . ?
C33 C36 H36A 109.4 . . ?
C38 C36 H36A 109.4 . . ?
C33 C36 H36B 109.4 . . ?
C38 C36 H36B 109.4 . . ?
H36A C36 H36B 108.0 . . ?
C45 C37 C32 122.2(13) . . ?
C45 C37 H37 118.9 . . ?
C32 C37 H37 118.9 . . ?
C31 C38 C36 108.3(10) . . ?
C31 C38 P2 115.5(8) . . ?
C36 C38 P2 110.2(8) . . ?
C31 C38 H38 107.5 . . ?
C36 C38 H38 107.5 . . ?
P2 C38 H38 107.5 . . ?
C43 C39 C48 111.7(13) . . ?
C43 C39 C31 114.6(12) . . ?
C48 C39 C31 110.3(12) . . ?
C43 C39 H39 106.6 . . ?
C48 C39 H39 106.6 . . ?
C31 C39 H39 106.6 . . ?
C45 C40 C30 122.6(13) . . ?
C45 C40 H40 118.7 . . ?
C30 C40 H40 118.7 . . ?
C42 C41 C29 122.4(15) . . ?
C42 C41 H41 118.8 . . ?
C29 C41 H41 118.8 . . ?
C46 C42 C41 119.4(15) . . ?
C46 C42 H42 120.3 . . ?
C41 C42 H42 120.3 . . ?
C39 C43 H43A 109.5 . . ?
C39 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C39 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C33 C44 H44A 109.5 . . ?
C33 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C33 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C37 C45 C40 118.6(14) . . ?
C37 C45 H45 120.7 . . ?
C40 C45 H45 120.7 . . ?
C42 C46 C34 122.6(16) . . ?
C42 C46 H46 118.7 . . ?
C34 C46 H46 118.7 . . ?
C31 C47 C35 112.5(12) . . ?
C31 C47 H47A 109.1 . . ?
C35 C47 H47A 109.1 . . ?
C31 C47 H47B 109.1 . . ?
C35 C47 H47B 109.1 . . ?
H47A C47 H47B 107.8 . . ?
C39 C48 H48A 109.5 . . ?
C39 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C39 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.077

_shelxl_version_number           2014/6



