# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_220813c
_database_code_depnum_ccdc_archive 'CCDC 2218943'
loop_
_audit_author_name
_audit_author_address
'Daqi Wang'
;Liaocheng University
China
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-02-22 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            'C34 H26 F3 O4 P S'
_chemical_formula_weight         618.58

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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.3536(8)
_cell_length_b                   11.2590(9)
_cell_length_c                   14.7083(12)
_cell_angle_alpha                91.0520(10)
_cell_angle_beta                 92.132(3)
_cell_angle_gamma                90.8130(10)
_cell_volume                     1547.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3332
_cell_measurement_theta_min      3.282
_cell_measurement_theta_max      25.554

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   0.909
_exptl_transmission_factor_max   0.919
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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            7806
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.179
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_full        25.018
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             5365
_reflns_number_gt                3902
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1012P)²+0.2212P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5365
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1679
_refine_ls_wR_factor_gt          0.1531
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_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 0.39430(7) 0.43001(6) 0.25796(5) 0.0380(2) Uani 1 1 d . . . . .
F1 F 0.9760(3) -0.0689(2) 0.09500(16) 0.0963(7) Uani 1 1 d . . . . .
F2 F 1.0429(3) 0.0891(3) 0.1685(2) 0.1435(13) Uani 1 1 d . . . . .
F3 F 0.8504(3) 0.0906(2) 0.08374(17) 0.1093(9) Uani 1 1 d . . . . .
O1 O 0.7722(3) 0.0919(2) 0.27188(17) 0.0761(7) Uani 1 1 d . . . . .
O2 O 0.7145(3) -0.0964(2) 0.1955(2) 0.0790(7) Uani 1 1 d . . . . .
O3 O 0.9249(4) -0.0813(3) 0.2945(2) 0.1065(10) Uani 1 1 d . . . . .
O4 O 0.6676(3) 0.68107(17) 0.28042(17) 0.0689(7) Uani 1 1 d . . . . .
H4 H 0.695346 0.746480 0.264159 0.103 Uiso 1 1 calc R U . . .
S1 S 0.82410(9) -0.01931(7) 0.23718(6) 0.0541(2) Uani 1 1 d . . . . .
C1 C 0.7591(3) 0.1058(3) 0.4964(2) 0.0642(9) Uani 1 1 d . . . . .
H1 H 0.826204 0.115757 0.451891 0.077 Uiso 1 1 calc R U . . .
C2 C 0.7780(4) 0.0176(4) 0.5601(3) 0.0790(11) Uani 1 1 d . . . . .
H2 H 0.857662 -0.030694 0.558384 0.095 Uiso 1 1 calc R U . . .
C3 C 0.6790(4) 0.0015(4) 0.6257(3) 0.0811(12) Uani 1 1 d . . . . .
H3 H 0.692184 -0.057215 0.668739 0.097 Uiso 1 1 calc R U . . .
C4 C 0.5617(5) 0.0717(4) 0.6277(3) 0.0896(13) Uani 1 1 d . . . . .
H4A H 0.494273 0.058840 0.671508 0.108 Uiso 1 1 calc R U . . .
C5 C 0.5402(4) 0.1628(3) 0.5653(2) 0.0701(10) Uani 1 1 d . . . . .
H5 H 0.460642 0.211155 0.568467 0.084 Uiso 1 1 calc R U . . .
C6 C 0.6405(3) 0.1801(3) 0.49808(18) 0.0453(7) Uani 1 1 d . . . . .
C7 C 0.6206(3) 0.2732(3) 0.43235(18) 0.0448(7) Uani 1 1 d . . . . .
C8 C 0.6040(3) 0.3514(2) 0.37842(18) 0.0418(6) Uani 1 1 d . . . . .
C9 C 0.5752(3) 0.4505(2) 0.31556(18) 0.0395(6) Uani 1 1 d . . . . .
H9 H 0.569725 0.522288 0.353931 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6933(3) 0.4750(2) 0.24828(18) 0.0389(6) Uani 1 1 d . . . . .
C11 C 0.7626(3) 0.3842(3) 0.2025(2) 0.0506(7) Uani 1 1 d . . . . .
H11 H 0.736142 0.305615 0.212193 0.061 Uiso 1 1 calc R U . . .
C12 C 0.8708(3) 0.4088(3) 0.1426(2) 0.0613(8) Uani 1 1 d . . . . .
H12 H 0.913510 0.347063 0.111232 0.074 Uiso 1 1 calc R U . . .
C13 C 0.9148(3) 0.5255(3) 0.1298(2) 0.0588(8) Uani 1 1 d . . . . .
H13 H 0.987825 0.542114 0.090536 0.071 Uiso 1 1 calc R U . . .
C14 C 0.8489(3) 0.6177(3) 0.1761(2) 0.0542(8) Uani 1 1 d . . . . .
H14 H 0.879068 0.695785 0.168264 0.065 Uiso 1 1 calc R U . . .
C15 C 0.7382(3) 0.5936(2) 0.23403(19) 0.0437(6) Uani 1 1 d . . . . .
C16 C 0.3895(3) 0.3101(2) 0.17467(18) 0.0396(6) Uani 1 1 d . . . . .
C17 C 0.3051(3) 0.3188(3) 0.0933(2) 0.0539(8) Uani 1 1 d . . . . .
H17 H 0.257599 0.388805 0.080358 0.065 Uiso 1 1 calc R U . . .
C18 C 0.2931(4) 0.2228(3) 0.0329(2) 0.0647(9) Uani 1 1 d . . . . .
H18 H 0.237633 0.228580 -0.020538 0.078 Uiso 1 1 calc R U . . .
C19 C 0.3640(3) 0.1182(3) 0.0523(2) 0.0601(8) Uani 1 1 d . . . . .
H19 H 0.356511 0.054407 0.011200 0.072 Uiso 1 1 calc R U . . .
C20 C 0.4456(3) 0.1080(3) 0.1321(2) 0.0540(8) Uani 1 1 d . . . . .
H20 H 0.491900 0.037287 0.144624 0.065 Uiso 1 1 calc R U . . .
C21 C 0.4586(3) 0.2033(2) 0.19360(19) 0.0463(7) Uani 1 1 d . . . . .
H21 H 0.513191 0.196057 0.247307 0.056 Uiso 1 1 calc R U . . .
C22 C 0.2671(3) 0.3957(2) 0.34367(18) 0.0409(6) Uani 1 1 d . . . . .
C23 C 0.1503(3) 0.3206(3) 0.3193(2) 0.0597(8) Uani 1 1 d . . . . .
H23 H 0.140337 0.288800 0.260553 0.072 Uiso 1 1 calc R U . . .
C24 C 0.0489(4) 0.2937(4) 0.3836(3) 0.0782(11) Uani 1 1 d . . . . .
H24 H -0.029412 0.245049 0.367195 0.094 Uiso 1 1 calc R U . . .
C25 C 0.0642(4) 0.3389(4) 0.4710(3) 0.0796(11) Uani 1 1 d . . . . .
H25 H -0.001513 0.318266 0.514132 0.096 Uiso 1 1 calc R U . . .
C26 C 0.1786(4) 0.4157(4) 0.4950(2) 0.0762(11) Uani 1 1 d . . . . .
H26 H 0.187756 0.447544 0.553751 0.091 Uiso 1 1 calc R U . . .
C27 C 0.2788(3) 0.4447(3) 0.4313(2) 0.0614(9) Uani 1 1 d . . . . .
H27 H 0.353838 0.496955 0.447207 0.074 Uiso 1 1 calc R U . . .
C28 C 0.3472(3) 0.5673(2) 0.2034(2) 0.0468(7) Uani 1 1 d . . . . .
C29 C 0.2529(3) 0.6448(3) 0.2448(3) 0.0606(8) Uani 1 1 d . . . . .
H29 H 0.212339 0.624721 0.299363 0.073 Uiso 1 1 calc R U . . .
C30 C 0.2196(4) 0.7527(3) 0.2039(3) 0.0807(12) Uani 1 1 d . . . . .
H30 H 0.158053 0.805066 0.231667 0.097 Uiso 1 1 calc R U . . .
C31 C 0.2783(4) 0.7812(3) 0.1220(4) 0.0955(15) Uani 1 1 d . . . . .
H31 H 0.255217 0.852648 0.094743 0.115 Uiso 1 1 calc R U . . .
C32 C 0.3713(4) 0.7044(4) 0.0803(3) 0.0904(14) Uani 1 1 d . . . . .
H32 H 0.409086 0.723995 0.024810 0.108 Uiso 1 1 calc R U . . .
C33 C 0.4084(3) 0.5980(3) 0.1213(2) 0.0656(9) Uani 1 1 d . . . . .
H33 H 0.473158 0.547666 0.094325 0.079 Uiso 1 1 calc R U . . .
C34 C 0.9292(4) 0.0251(3) 0.1427(2) 0.0662(9) Uani 1 1 d . . . . .


_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 C16 1.805(3) . ?
P1 C28 1.807(3) . ?
P1 C22 1.808(3) . ?
P1 C9 1.873(3) . ?
F1 C34 1.346(4) . ?
F2 C34 1.316(4) . ?
F3 C34 1.353(4) . ?
O1 S1 1.441(2) . ?
O2 S1 1.446(2) . ?
O3 S1 1.437(3) . ?
O4 C15 1.378(3) . ?
S1 C34 1.806(4) . ?
C1 C2 1.386(4) . ?
C1 C6 1.400(4) . ?
C2 C3 1.375(5) . ?
C3 C4 1.362(6) . ?
C4 C5 1.400(5) . ?
C5 C6 1.402(4) . ?
C6 C7 1.448(4) . ?
C7 C8 1.204(4) . ?
C8 C9 1.483(4) . ?
C9 C10 1.536(4) . ?
C10 C11 1.395(4) . ?
C10 C15 1.416(4) . ?
C11 C12 1.395(4) . ?
C12 C13 1.390(4) . ?
C13 C14 1.394(4) . ?
C14 C15 1.391(4) . ?
C16 C21 1.401(4) . ?
C16 C17 1.414(4) . ?
C17 C18 1.386(5) . ?
C18 C19 1.389(5) . ?
C19 C20 1.384(4) . ?
C20 C21 1.392(4) . ?
C22 C27 1.392(4) . ?
C22 C23 1.404(4) . ?
C23 C24 1.398(4) . ?
C24 C25 1.375(5) . ?
C25 C26 1.397(5) . ?
C26 C27 1.389(4) . ?
C28 C29 1.397(4) . ?
C28 C33 1.403(4) . ?
C29 C30 1.399(5) . ?
C30 C31 1.383(6) . ?
C31 C32 1.387(6) . ?
C32 C33 1.393(5) . ?

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
C16 P1 C28 109.69(13) . . ?
C16 P1 C22 108.24(12) . . ?
C28 P1 C22 109.99(13) . . ?
C16 P1 C9 112.40(12) . . ?
C28 P1 C9 108.24(12) . . ?
C22 P1 C9 108.27(12) . . ?
O3 S1 O1 116.93(18) . . ?
O3 S1 O2 113.15(19) . . ?
O1 S1 O2 114.38(16) . . ?
O3 S1 C34 103.31(19) . . ?
O1 S1 C34 103.12(16) . . ?
O2 S1 C34 103.67(16) . . ?
C2 C1 C6 120.9(3) . . ?
C3 C2 C1 120.1(3) . . ?
C4 C3 C2 119.9(3) . . ?
C3 C4 C5 121.6(3) . . ?
C4 C5 C6 119.0(3) . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 121.2(3) . . ?
C5 C6 C7 120.2(3) . . ?
C8 C7 C6 179.3(3) . . ?
C7 C8 C9 176.1(3) . . ?
C8 C9 C10 115.0(2) . . ?
C8 C9 P1 110.06(17) . . ?
C10 C9 P1 112.73(17) . . ?
C11 C10 C15 118.1(2) . . ?
C11 C10 C9 122.5(2) . . ?
C15 C10 C9 119.4(2) . . ?
C12 C11 C10 121.3(3) . . ?
C13 C12 C11 120.0(3) . . ?
C12 C13 C14 119.7(3) . . ?
C15 C14 C13 120.4(3) . . ?
O4 C15 C14 123.0(2) . . ?
O4 C15 C10 116.5(2) . . ?
C14 C15 C10 120.4(3) . . ?
C21 C16 C17 119.2(3) . . ?
C21 C16 P1 120.3(2) . . ?
C17 C16 P1 120.3(2) . . ?
C18 C17 C16 120.0(3) . . ?
C17 C18 C19 120.0(3) . . ?
C20 C19 C18 120.6(3) . . ?
C19 C20 C21 120.2(3) . . ?
C20 C21 C16 120.0(3) . . ?
C27 C22 C23 119.4(3) . . ?
C27 C22 P1 122.2(2) . . ?
C23 C22 P1 118.4(2) . . ?
C24 C23 C22 119.8(3) . . ?
C25 C24 C23 120.3(3) . . ?
C24 C25 C26 120.0(3) . . ?
C27 C26 C25 120.2(3) . . ?
C26 C27 C22 120.2(3) . . ?
C29 C28 C33 120.0(3) . . ?
C29 C28 P1 119.7(2) . . ?
C33 C28 P1 120.3(2) . . ?
C28 C29 C30 119.7(4) . . ?
C31 C30 C29 119.9(4) . . ?
C30 C31 C32 120.6(3) . . ?
C31 C32 C33 120.2(4) . . ?
C32 C33 C28 119.5(4) . . ?
F2 C34 F1 106.9(3) . . ?
F2 C34 F3 107.5(3) . . ?
F1 C34 F3 106.7(3) . . ?
F2 C34 S1 112.6(3) . . ?
F1 C34 S1 112.1(2) . . ?
F3 C34 S1 110.7(3) . . ?

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_211113e
_database_code_depnum_ccdc_archive 'CCDC 2218944'
loop_
_audit_author_name
_audit_author_address
'Daqi Wang'
;Liaocheng University
China
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-02-22 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            'C34 H26 F3 O4 P S'
_chemical_formula_weight         618.58

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.7924(8)
_cell_length_b                   10.8723(9)
_cell_length_c                   16.3126(14)
_cell_angle_alpha                98.275(2)
_cell_angle_beta                 97.020(2)
_cell_angle_gamma                116.223(4)
_cell_volume                     1507.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1900
_cell_measurement_theta_min      2.371
_cell_measurement_theta_max      27.0985

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   0.947
_exptl_transmission_factor_max   0.979
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.979
_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            7386
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.142
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             5199
_reflns_number_gt                3238
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 SHELXTL'
_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)+(0.1108P)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_number_reflns         5199
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1939
_refine_ls_wR_factor_gt          0.1738
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.000
_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 0.16617(11) 0.84764(9) 0.26056(6) 0.0337(3) Uani 1 1 d . . . . .
S1 S 0.01266(13) 0.72584(11) 0.72148(7) 0.0500(3) Uani 1 1 d . . . . .
O1 O 0.3567(3) 1.2610(2) 0.26919(16) 0.0450(7) Uani 1 1 d . . . . .
C29 C 0.3613(4) 1.1247(4) 0.3619(2) 0.0338(8) Uani 1 1 d . . . . .
C6 C 0.0624(4) 0.8061(4) 0.3455(2) 0.0351(9) Uani 1 1 d . . . . .
C27 C 0.2623(4) 1.0342(3) 0.2792(2) 0.0331(8) Uani 1 1 d . . . . .
C18 C 0.3103(4) 0.7871(4) 0.2623(2) 0.0354(9) Uani 1 1 d . . . . .
C26 C 0.2640(4) 1.1233(4) 0.2273(2) 0.0389(9) Uani 1 1 d . . . . .
C28 C 0.4168(5) 1.2612(4) 0.3508(2) 0.0395(9) Uani 1 1 d . . . . .
O4 O -0.1005(4) 0.6157(3) 0.6512(2) 0.0727(10) Uani 1 1 d . . . . .
C30 C 0.4103(5) 1.1028(4) 0.4406(2) 0.0442(10) Uani 1 1 d . . . . .
H30 H 0.3749 1.0126 0.4504 0.053 Uiso 1 1 calc R U . . .
C5 C -0.0208(4) 0.8782(4) 0.3660(2) 0.0426(9) Uani 1 1 d . . . . .
H5 H -0.0197 0.9465 0.3374 0.051 Uiso 1 1 calc R U . . .
C11 C 0.4687(4) 0.8821(4) 0.2780(2) 0.0402(9) Uani 1 1 d . . . . .
H11 H 0.5012 0.9783 0.2883 0.048 Uiso 1 1 calc R U . . .
C33 C 0.5204(5) 1.3804(4) 0.4125(3) 0.0497(11) Uani 1 1 d . . . . .
H33 H 0.5555 1.4705 0.4027 0.060 Uiso 1 1 calc R U . . .
C7 C 0.2614(5) 0.6422(4) 0.2461(2) 0.0463(10) Uani 1 1 d . . . . .
H7 H 0.1559 0.5785 0.2341 0.056 Uiso 1 1 calc R U . . .
C25 C 0.1892(5) 1.1049(4) 0.1380(2) 0.0443(10) Uani 1 1 d . . . . .
H25A H 0.1488 1.1717 0.1366 0.053 Uiso 1 1 calc R U . . .
H25B H 0.1012 1.0113 0.1199 0.053 Uiso 1 1 calc R U . . .
F2 F 0.3132(3) 0.8142(3) 0.7677(2) 0.0943(10) Uani 1 1 d . . . . .
C24 C 0.2942(5) 1.1240(4) 0.0749(2) 0.0471(10) Uani 1 1 d . . . . .
C17 C 0.0323(5) 0.7627(4) 0.1590(2) 0.0410(9) Uani 1 1 d . . . . .
O3 O -0.0090(4) 0.6967(3) 0.80317(19) 0.0718(10) Uani 1 1 d . . . . .
C10 C 0.5764(5) 0.8332(4) 0.2781(3) 0.0533(11) Uani 1 1 d . . . . .
H10 H 0.6819 0.8963 0.2879 0.064 Uiso 1 1 calc R U . . .
O2 O 0.0503(4) 0.8669(3) 0.7162(2) 0.0860(11) Uani 1 1 d . . . . .
C1 C 0.0605(5) 0.7038(4) 0.3889(2) 0.0489(11) Uani 1 1 d . . . . .
H1 H 0.1139 0.6538 0.3751 0.059 Uiso 1 1 calc R U . . .
C4 C -0.1051(5) 0.8477(4) 0.4294(3) 0.0546(11) Uani 1 1 d . . . . .
H4 H -0.1611 0.8955 0.4426 0.066 Uiso 1 1 calc R U . . .
C3 C -0.1070(5) 0.7476(5) 0.4732(3) 0.0567(12) Uani 1 1 d . . . . .
H3 H -0.1642 0.7276 0.5154 0.068 Uiso 1 1 calc R U . . .
C32 C 0.5679(5) 1.3561(4) 0.4893(3) 0.0549(12) Uani 1 1 d . . . . .
H32 H 0.6379 1.4322 0.5326 0.066 Uiso 1 1 calc R U . . .
C31 C 0.5135(5) 1.2204(4) 0.5034(2) 0.0514(11) Uani 1 1 d . . . . .
H31 H 0.5469 1.2083 0.5561 0.062 Uiso 1 1 calc R U . . .
C9 C 0.5277(5) 0.6891(5) 0.2634(3) 0.0575(12) Uani 1 1 d . . . . .
H9 H 0.6011 0.6567 0.2641 0.069 Uiso 1 1 calc R U . . .
C8 C 0.3715(5) 0.5943(4) 0.2480(3) 0.0535(11) Uani 1 1 d . . . . .
H8 H 0.3400 0.4984 0.2388 0.064 Uiso 1 1 calc R U . . .
F3 F 0.1812(5) 0.5945(4) 0.7227(3) 0.1459(18) Uani 1 1 d . . . . .
C2 C -0.0234(6) 0.6777(5) 0.4538(3) 0.0639(13) Uani 1 1 d . . . . .
H2 H -0.0225 0.6120 0.4843 0.077 Uiso 1 1 calc R U . . .
C12 C 0.0876(6) 0.7351(5) 0.0876(3) 0.0630(13) Uani 1 1 d . . . . .
H12 H 0.1927 0.7604 0.0922 0.076 Uiso 1 1 calc R U . . .
F1 F 0.2251(5) 0.7365(6) 0.6367(3) 0.157(2) Uani 1 1 d . . . . .
C34 C 0.1912(6) 0.7183(5) 0.7114(4) 0.0720(14) Uani 1 1 d . . . . .
C13 C -0.0147(8) 0.6696(5) 0.0090(3) 0.0772(16) Uani 1 1 d . . . . .
H13 H 0.0223 0.6515 -0.0388 0.093 Uiso 1 1 calc R U . . .
C23 C 0.4487(6) 1.2279(6) 0.0929(3) 0.0744(15) Uani 1 1 d . . . . .
H23 H 0.4922 1.2874 0.1464 0.089 Uiso 1 1 calc R U . . .
C16 C -0.1237(6) 0.7259(6) 0.1508(3) 0.0772(16) Uani 1 1 d . . . . .
H16 H -0.1620 0.7451 0.1978 0.093 Uiso 1 1 calc R U . . .
C19 C 0.2333(7) 1.0379(5) -0.0067(3) 0.0686(14) Uani 1 1 d . . . . .
H19 H 0.1305 0.9673 -0.0206 0.082 Uiso 1 1 calc R U . . .
C14 C -0.1699(8) 0.6317(5) 0.0022(3) 0.0849(18) Uani 1 1 d . . . . .
H14 H -0.2385 0.5866 -0.0500 0.102 Uiso 1 1 calc R U . . .
C22 C 0.5393(7) 1.2440(8) 0.0315(4) 0.111(2) Uani 1 1 d . . . . .
H22 H 0.6428 1.3131 0.0447 0.133 Uiso 1 1 calc R U . . .
C21 C 0.4770(9) 1.1593(9) -0.0475(4) 0.125(3) Uani 1 1 d . . . . .
H21 H 0.5378 1.1710 -0.0882 0.150 Uiso 1 1 calc R U . . .
C15 C -0.2230(7) 0.6603(7) 0.0721(4) 0.102(2) Uani 1 1 d . . . . .
H15 H -0.3281 0.6352 0.0670 0.122 Uiso 1 1 calc R U . . .
C20 C 0.3251(9) 1.0569(8) -0.0672(4) 0.103(2) Uani 1 1 d . . . . .
H20 H 0.2829 0.9996 -0.1214 0.124 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 C27 1.777(3) . ?
P1 C18 1.801(4) . ?
P1 C6 1.809(4) . ?
P1 C17 1.810(4) . ?
S1 O2 1.429(3) . ?
S1 O3 1.432(3) . ?
S1 O4 1.448(3) . ?
S1 C34 1.811(6) . ?
O1 C26 1.374(4) . ?
O1 C28 1.388(4) . ?
C29 C28 1.385(5) . ?
C29 C30 1.405(5) . ?
C29 C27 1.478(5) . ?
C6 C5 1.395(5) . ?
C6 C1 1.397(5) . ?
C27 C26 1.371(5) . ?
C18 C11 1.396(5) . ?
C18 C7 1.401(5) . ?
C26 C25 1.492(5) . ?
C28 C33 1.390(5) . ?
C30 C31 1.390(5) . ?
C5 C4 1.388(5) . ?
C11 C10 1.376(6) . ?
C33 C32 1.386(6) . ?
C7 C8 1.389(6) . ?
C25 C24 1.514(5) . ?
F2 C34 1.309(5) . ?
C24 C23 1.392(6) . ?
C24 C19 1.399(6) . ?
C17 C16 1.381(6) . ?
C17 C12 1.392(6) . ?
C10 C9 1.393(6) . ?
C1 C2 1.403(6) . ?
C4 C3 1.380(6) . ?
C3 C2 1.375(6) . ?
C32 C31 1.395(6) . ?
C9 C8 1.380(6) . ?
F3 C34 1.347(6) . ?
C12 C13 1.395(6) . ?
F1 C34 1.321(6) . ?
C13 C14 1.373(8) . ?
C23 C22 1.396(7) . ?
C16 C15 1.386(7) . ?
C19 C20 1.392(8) . ?
C14 C15 1.362(8) . ?
C22 C21 1.360(8) . ?
C21 C20 1.369(9) . ?

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
C27 P1 C18 108.69(17) . . ?
C27 P1 C6 105.50(16) . . ?
C18 P1 C6 111.84(16) . . ?
C27 P1 C17 113.63(17) . . ?
C18 P1 C17 107.08(17) . . ?
C6 P1 C17 110.19(18) . . ?
O2 S1 O3 114.3(2) . . ?
O2 S1 O4 116.5(2) . . ?
O3 S1 O4 114.3(2) . . ?
O2 S1 C34 102.9(2) . . ?
O3 S1 C34 103.5(2) . . ?
O4 S1 C34 102.9(2) . . ?
C26 O1 C28 107.5(3) . . ?
C28 C29 C30 118.8(3) . . ?
C28 C29 C27 105.3(3) . . ?
C30 C29 C27 135.9(3) . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 P1 117.7(3) . . ?
C1 C6 P1 122.6(3) . . ?
C26 C27 C29 106.2(3) . . ?
C26 C27 P1 131.2(3) . . ?
C29 C27 P1 122.5(2) . . ?
C11 C18 C7 120.0(4) . . ?
C11 C18 P1 121.0(3) . . ?
C7 C18 P1 119.1(3) . . ?
C27 C26 O1 110.7(3) . . ?
C27 C26 C25 135.1(3) . . ?
O1 C26 C25 114.2(3) . . ?
C29 C28 O1 110.2(3) . . ?
C29 C28 C33 124.5(4) . . ?
O1 C28 C33 125.3(3) . . ?
C31 C30 C29 117.8(4) . . ?
C4 C5 C6 119.8(4) . . ?
C10 C11 C18 119.9(4) . . ?
C32 C33 C28 115.7(4) . . ?
C8 C7 C18 119.6(4) . . ?
C26 C25 C24 115.3(3) . . ?
C23 C24 C19 117.6(4) . . ?
C23 C24 C25 123.1(4) . . ?
C19 C24 C25 119.3(4) . . ?
C16 C17 C12 119.2(4) . . ?
C16 C17 P1 121.2(3) . . ?
C12 C17 P1 119.6(3) . . ?
C11 C10 C9 120.1(4) . . ?
C6 C1 C2 118.9(4) . . ?
C3 C4 C5 120.9(4) . . ?
C2 C3 C4 119.4(4) . . ?
C33 C32 C31 121.6(4) . . ?
C30 C31 C32 121.6(4) . . ?
C8 C9 C10 120.6(4) . . ?
C9 C8 C7 119.9(4) . . ?
C3 C2 C1 121.2(4) . . ?
C17 C12 C13 120.0(5) . . ?
F2 C34 F1 106.0(5) . . ?
F2 C34 F3 105.2(4) . . ?
F1 C34 F3 109.0(5) . . ?
F2 C34 S1 113.7(4) . . ?
F1 C34 S1 111.6(4) . . ?
F3 C34 S1 111.0(4) . . ?
C14 C13 C12 120.0(5) . . ?
C24 C23 C22 120.8(5) . . ?
C17 C16 C15 119.6(5) . . ?
C20 C19 C24 120.6(5) . . ?
C15 C14 C13 119.8(5) . . ?
C21 C22 C23 120.4(6) . . ?
C22 C21 C20 120.1(6) . . ?
C14 C15 C16 121.4(6) . . ?
C21 C20 C19 120.4(5) . . ?

_refine_diff_density_max         0.495
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.064

_shelxl_version_number           2014/6



