# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_nik44
_database_code_depnum_ccdc_archive 'CCDC 2373866'
loop_
_audit_author_name
_audit_author_address
'Helge Mueller-Bunz'
;UCD, Belfield, Dublin  
Ireland
;
_audit_update_record             
;
2024-07-26 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H32 O P, C F3 O3 S'
_chemical_formula_sum            'C32 H32 F3 O4 P S'
_chemical_formula_weight         600.61
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   17.0140(2)
_cell_length_b                   9.10342(11)
_cell_length_c                   18.8380(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2917.74(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13813
_cell_measurement_theta_min      3.4400
_cell_measurement_theta_max      29.2230

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2179
_exptl_crystal_size_mid          0.1229
_exptl_crystal_size_min          0.1153
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;

_exptl_special_details           
; 
 3604 Friedel pairs were measured. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29792
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         29.51
_reflns_number_total             7057
_reflns_number_gt                6667
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0315P)²+0.6198P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(4)
_refine_ls_number_reflns         7057
_refine_ls_number_parameters     370
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.12637(2) 0.68507(4) 0.31233(2) 0.01220(8) Uani 1 1 d . . .
O1 O 0.06029(6) 0.49715(11) 0.39549(6) 0.0152(2) Uani 1 1 d . . .
C1 C 0.12204(8) 0.49314(16) 0.34510(8) 0.0135(3) Uani 1 1 d . . .
H1 H 0.1068 0.4268 0.3051 0.016 Uiso 1 1 calc R . .
C2 C 0.19969(8) 0.44229(16) 0.37578(8) 0.0139(3) Uani 1 1 d . . .
C3 C 0.25174(9) 0.36207(17) 0.33418(9) 0.0172(3) Uani 1 1 d . . .
H3 H 0.2390 0.3404 0.2862 0.021 Uiso 1 1 calc R . .
C4 C 0.32265(9) 0.31347(18) 0.36283(9) 0.0204(3) Uani 1 1 d . . .
H4 H 0.3584 0.2595 0.3342 0.025 Uiso 1 1 calc R . .
C5 C 0.34113(9) 0.34383(18) 0.43318(9) 0.0208(3) Uani 1 1 d . . .
H5 H 0.3891 0.3090 0.4528 0.025 Uiso 1 1 calc R . .
C6 C 0.28970(9) 0.42484(18) 0.47473(9) 0.0200(3) Uani 1 1 d . . .
H6 H 0.3026 0.4466 0.5227 0.024 Uiso 1 1 calc R . .
C7 C 0.21901(9) 0.47430(17) 0.44607(8) 0.0163(3) Uani 1 1 d . . .
H7 H 0.1838 0.5300 0.4745 0.020 Uiso 1 1 calc R . .
C8 C 0.03441(9) 0.35441(16) 0.42161(8) 0.0138(3) Uani 1 1 d . . .
H8 H 0.0804 0.2864 0.4252 0.017 Uiso 1 1 calc R . .
C9 C 0.00097(9) 0.38297(18) 0.49510(8) 0.0183(3) Uani 1 1 d . . .
H9A H -0.0388 0.4621 0.4923 0.022 Uiso 1 1 calc R . .
H9B H 0.0436 0.4164 0.5270 0.022 Uiso 1 1 calc R . .
C10 C -0.03684(10) 0.2443(2) 0.52569(9) 0.0234(4) Uani 1 1 d . . .
H10A H -0.0619 0.2680 0.5717 0.028 Uiso 1 1 calc R . .
H10B H 0.0044 0.1697 0.5345 0.028 Uiso 1 1 calc R . .
C11 C -0.09882(10) 0.1804(2) 0.47493(10) 0.0260(4) Uani 1 1 d . . .
H11A H -0.1201 0.0880 0.4949 0.031 Uiso 1 1 calc R . .
H11B H -0.1428 0.2508 0.4697 0.031 Uiso 1 1 calc R . .
C12 C -0.06240(10) 0.15007(18) 0.40256(9) 0.0211(3) Uani 1 1 d . . .
H12A H -0.1032 0.1124 0.3698 0.025 Uiso 1 1 calc R . .
H12B H -0.0212 0.0740 0.4073 0.025 Uiso 1 1 calc R . .
C13 C -0.02637(9) 0.29045(17) 0.37176(8) 0.0167(3) Uani 1 1 d . . .
H13A H -0.0014 0.2680 0.3255 0.020 Uiso 1 1 calc R . .
H13B H -0.0684 0.3637 0.3635 0.020 Uiso 1 1 calc R . .
C14 C 0.13839(9) 0.81073(17) 0.38547(8) 0.0151(3) Uani 1 1 d . . .
C15 C 0.08615(9) 0.80408(17) 0.44279(9) 0.0167(3) Uani 1 1 d . . .
H15 H 0.0459 0.7317 0.4438 0.020 Uiso 1 1 calc R . .
C16 C 0.09336(9) 0.90356(18) 0.49810(9) 0.0189(3) Uani 1 1 d . . .
H16 H 0.0583 0.8989 0.5373 0.023 Uiso 1 1 calc R . .
C17 C 0.15160(10) 1.00970(19) 0.49641(9) 0.0221(4) Uani 1 1 d . . .
H17 H 0.1566 1.0768 0.5348 0.026 Uiso 1 1 calc R . .
C18 C 0.20263(10) 1.01905(19) 0.43940(10) 0.0242(4) Uani 1 1 d . . .
H18 H 0.2421 1.0928 0.4385 0.029 Uiso 1 1 calc R . .
C19 C 0.19606(9) 0.92011(18) 0.38319(9) 0.0201(3) Uani 1 1 d . . .
H19 H 0.2305 0.9270 0.3436 0.024 Uiso 1 1 calc R . .
C20 C 0.20686(9) 0.70161(16) 0.25132(8) 0.0136(3) Uani 1 1 d . . .
C21 C 0.28482(9) 0.69195(16) 0.27503(9) 0.0161(3) Uani 1 1 d . . .
H21 H 0.2958 0.6786 0.3241 0.019 Uiso 1 1 calc R . .
C22 C 0.34560(9) 0.70196(17) 0.22653(9) 0.0182(3) Uani 1 1 d . . .
H22 H 0.3985 0.6958 0.2423 0.022 Uiso 1 1 calc R . .
C23 C 0.32963(9) 0.72099(17) 0.15477(9) 0.0190(3) Uani 1 1 d . . .
H23 H 0.3717 0.7275 0.1218 0.023 Uiso 1 1 calc R . .
C24 C 0.25276(10) 0.73047(18) 0.13114(8) 0.0200(3) Uani 1 1 d . . .
H24 H 0.2421 0.7436 0.0820 0.024 Uiso 1 1 calc R . .
C25 C 0.19126(9) 0.72066(17) 0.17939(8) 0.0169(3) Uani 1 1 d . . .
H25 H 0.1385 0.7270 0.1633 0.020 Uiso 1 1 calc R . .
C26 C 0.03608(9) 0.73028(17) 0.26751(8) 0.0142(3) Uani 1 1 d . . .
C27 C 0.01504(9) 0.87787(17) 0.26208(9) 0.0192(3) Uani 1 1 d . . .
H27 H 0.0460 0.9512 0.2845 0.023 Uiso 1 1 calc R . .
C28 C -0.05158(9) 0.91727(18) 0.22370(9) 0.0223(3) Uani 1 1 d . . .
H28 H -0.0661 1.0177 0.2198 0.027 Uiso 1 1 calc R . .
C29 C -0.09650(9) 0.81058(19) 0.19133(9) 0.0213(4) Uani 1 1 d . . .
H29 H -0.1420 0.8381 0.1652 0.026 Uiso 1 1 calc R . .
C30 C -0.07611(9) 0.66367(19) 0.19640(9) 0.0196(3) Uani 1 1 d . . .
H30 H -0.1076 0.5911 0.1740 0.023 Uiso 1 1 calc R . .
C31 C -0.00932(9) 0.62233(17) 0.23439(8) 0.0160(3) Uani 1 1 d . . .
H31 H 0.0052 0.5218 0.2377 0.019 Uiso 1 1 calc R . .
S1 S 0.08558(2) 0.28757(4) 0.14541(2) 0.01714(8) Uani 1 1 d . . .
F1 F 0.18604(7) 0.10370(14) 0.20339(7) 0.0419(3) Uani 1 1 d . . .
F2 F 0.10818(7) 0.00617(10) 0.12718(6) 0.0327(3) Uani 1 1 d . . .
F3 F 0.20458(7) 0.14051(15) 0.09192(7) 0.0438(3) Uani 1 1 d . . .
O2 O 0.04862(8) 0.28772(15) 0.07717(7) 0.0333(3) Uani 1 1 d . . .
O3 O 0.03468(7) 0.25415(15) 0.20422(7) 0.0305(3) Uani 1 1 d . . .
O4 O 0.13945(8) 0.40589(14) 0.15846(8) 0.0367(3) Uani 1 1 d . . .
C32 C 0.14929(9) 0.12673(18) 0.14189(10) 0.0218(3) 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 C20 1.7941(16) . ?
P1 C26 1.8005(15) . ?
P1 C14 1.8026(16) . ?
P1 C1 1.8545(15) . ?
O1 C1 1.4163(18) . ?
O1 C8 1.4576(17) . ?
C1 C2 1.515(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.390(2) . ?
C2 C7 1.395(2) . ?
C3 C4 1.394(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.513(2) . ?
C8 C9 1.519(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.530(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.538(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.523(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.531(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.399(2) . ?
C14 C15 1.400(2) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.395(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.392(2) . ?
C20 C21 1.402(2) . ?
C21 C22 1.383(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.394(2) . ?
C26 C31 1.397(2) . ?
C27 C28 1.391(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.378(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.385(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.395(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
S1 O2 1.4311(14) . ?
S1 O4 1.4355(13) . ?
S1 O3 1.4387(13) . ?
S1 C32 1.8230(16) . ?
F1 C32 1.333(2) . ?
F2 C32 1.3306(19) . ?
F3 C32 1.337(2) . ?

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
C20 P1 C26 109.37(7) . . ?
C20 P1 C14 110.47(7) . . ?
C26 P1 C14 108.07(7) . . ?
C20 P1 C1 108.83(7) . . ?
C26 P1 C1 109.73(7) . . ?
C14 P1 C1 110.36(7) . . ?
C1 O1 C8 115.30(11) . . ?
O1 C1 C2 113.53(12) . . ?
O1 C1 P1 103.20(9) . . ?
C2 C1 P1 112.36(10) . . ?
O1 C1 H1 109.2 . . ?
C2 C1 H1 109.2 . . ?
P1 C1 H1 109.2 . . ?
C3 C2 C7 119.66(14) . . ?
C3 C2 C1 120.09(14) . . ?
C7 C2 C1 120.25(14) . . ?
C2 C3 C4 120.00(15) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.13(16) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 120.08(15) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 119.88(16) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 120.24(15) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
O1 C8 C13 109.88(12) . . ?
O1 C8 C9 105.56(12) . . ?
C13 C8 C9 112.04(13) . . ?
O1 C8 H8 109.8 . . ?
C13 C8 H8 109.8 . . ?
C9 C8 H8 109.8 . . ?
C8 C9 C10 111.07(13) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 111.49(14) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 110.25(14) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 110.54(14) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C8 C13 C12 111.07(13) . . ?
C8 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C8 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C19 C14 C15 120.00(15) . . ?
C19 C14 P1 120.53(12) . . ?
C15 C14 P1 119.35(12) . . ?
C16 C15 C14 119.70(15) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.14(15) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.66(15) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.95(15) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 119.52(15) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
C25 C20 C21 119.89(15) . . ?
C25 C20 P1 119.25(11) . . ?
C21 C20 P1 120.84(12) . . ?
C22 C21 C20 119.52(15) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.31(15) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 120.35(15) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.82(15) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C20 120.11(14) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
C27 C26 C31 120.21(14) . . ?
C27 C26 P1 118.28(12) . . ?
C31 C26 P1 121.35(12) . . ?
C28 C27 C26 119.72(15) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C29 C28 C27 119.99(15) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.74(15) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C31 120.00(15) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 C26 119.33(14) . . ?
C30 C31 H31 120.3 . . ?
C26 C31 H31 120.3 . . ?
O2 S1 O4 115.71(9) . . ?
O2 S1 O3 115.30(9) . . ?
O4 S1 O3 114.28(9) . . ?
O2 S1 C32 103.26(8) . . ?
O4 S1 C32 103.26(8) . . ?
O3 S1 C32 102.48(8) . . ?
F2 C32 F1 107.33(14) . . ?
F2 C32 F3 107.50(14) . . ?
F1 C32 F3 107.26(14) . . ?
F2 C32 S1 110.95(11) . . ?
F1 C32 S1 111.94(12) . . ?
F3 C32 S1 111.63(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 O1 C1 C2 -68.16(16) . . . . ?
C8 O1 C1 P1 169.96(10) . . . . ?
C20 P1 C1 O1 176.35(9) . . . . ?
C26 P1 C1 O1 -64.01(11) . . . . ?
C14 P1 C1 O1 54.97(11) . . . . ?
C20 P1 C1 C2 53.68(13) . . . . ?
C26 P1 C1 C2 173.31(11) . . . . ?
C14 P1 C1 C2 -67.70(12) . . . . ?
O1 C1 C2 C3 146.81(13) . . . . ?
P1 C1 C2 C3 -96.55(15) . . . . ?
O1 C1 C2 C7 -32.51(19) . . . . ?
P1 C1 C2 C7 84.12(15) . . . . ?
C7 C2 C3 C4 0.3(2) . . . . ?
C1 C2 C3 C4 -179.04(13) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C5 C6 C7 C2 0.2(2) . . . . ?
C3 C2 C7 C6 -0.7(2) . . . . ?
C1 C2 C7 C6 178.63(14) . . . . ?
C1 O1 C8 C13 -85.67(15) . . . . ?
C1 O1 C8 C9 153.33(12) . . . . ?
O1 C8 C9 C10 173.76(13) . . . . ?
C13 C8 C9 C10 54.19(18) . . . . ?
C8 C9 C10 C11 -54.34(19) . . . . ?
C9 C10 C11 C12 56.2(2) . . . . ?
C10 C11 C12 C13 -57.19(19) . . . . ?
O1 C8 C13 C12 -172.72(12) . . . . ?
C9 C8 C13 C12 -55.71(17) . . . . ?
C11 C12 C13 C8 57.21(18) . . . . ?
C20 P1 C14 C19 10.82(15) . . . . ?
C26 P1 C14 C19 -108.79(14) . . . . ?
C1 P1 C14 C19 131.22(13) . . . . ?
C20 P1 C14 C15 -173.26(12) . . . . ?
C26 P1 C14 C15 67.13(13) . . . . ?
C1 P1 C14 C15 -52.87(14) . . . . ?
C19 C14 C15 C16 -1.9(2) . . . . ?
P1 C14 C15 C16 -177.82(12) . . . . ?
C14 C15 C16 C17 0.5(2) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C14 -0.9(2) . . . . ?
C15 C14 C19 C18 2.1(2) . . . . ?
P1 C14 C19 C18 177.96(13) . . . . ?
C26 P1 C20 C25 -10.32(14) . . . . ?
C14 P1 C20 C25 -129.15(12) . . . . ?
C1 P1 C20 C25 109.55(13) . . . . ?
C26 P1 C20 C21 171.27(12) . . . . ?
C14 P1 C20 C21 52.44(14) . . . . ?
C1 P1 C20 C21 -68.87(14) . . . . ?
C25 C20 C21 C22 0.2(2) . . . . ?
P1 C20 C21 C22 178.61(12) . . . . ?
C20 C21 C22 C23 -0.2(2) . . . . ?
C21 C22 C23 C24 0.2(2) . . . . ?
C22 C23 C24 C25 -0.1(2) . . . . ?
C23 C24 C25 C20 0.1(2) . . . . ?
C21 C20 C25 C24 -0.2(2) . . . . ?
P1 C20 C25 C24 -178.59(12) . . . . ?
C20 P1 C26 C27 -83.85(14) . . . . ?
C14 P1 C26 C27 36.45(14) . . . . ?
C1 P1 C26 C27 156.84(12) . . . . ?
C20 P1 C26 C31 91.60(14) . . . . ?
C14 P1 C26 C31 -148.09(13) . . . . ?
C1 P1 C26 C31 -27.70(15) . . . . ?
C31 C26 C27 C28 0.2(2) . . . . ?
P1 C26 C27 C28 175.71(13) . . . . ?
C26 C27 C28 C29 0.1(3) . . . . ?
C27 C28 C29 C30 -0.1(3) . . . . ?
C28 C29 C30 C31 -0.2(3) . . . . ?
C29 C30 C31 C26 0.5(2) . . . . ?
C27 C26 C31 C30 -0.5(2) . . . . ?
P1 C26 C31 C30 -175.86(12) . . . . ?
O2 S1 C32 F2 -56.68(14) . . . . ?
O4 S1 C32 F2 -177.56(13) . . . . ?
O3 S1 C32 F2 63.44(14) . . . . ?
O2 S1 C32 F1 -176.55(12) . . . . ?
O4 S1 C32 F1 62.56(14) . . . . ?
O3 S1 C32 F1 -56.43(14) . . . . ?
O2 S1 C32 F3 63.20(14) . . . . ?
O4 S1 C32 F3 -57.69(14) . . . . ?
O3 S1 C32 F3 -176.68(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.898
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.044
_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_nik46
_database_code_depnum_ccdc_archive 'CCDC 2373867'
loop_
_audit_author_name
_audit_author_address
'Helge Mueller-Bunz'
;UCD, Belfield, Dublin  
Ireland
;
_audit_update_record             
;
2024-07-26 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H25 Cl3 O P, C F3 O3 S'
_chemical_formula_sum            'C29 H25 Cl3 F3 O4 P S'
_chemical_formula_weight         663.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.49648(7)
_cell_length_b                   16.70850(12)
_cell_length_c                   18.79840(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.9804(6)
_cell_angle_gamma                90.00
_cell_volume                     2966.54(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    29976
_cell_measurement_theta_min      3.5200
_cell_measurement_theta_max      76.3960

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.0989
_exptl_crystal_size_mid          0.0748
_exptl_crystal_size_min          0.0555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    4.437
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            61025
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.55
_diffrn_reflns_theta_max         76.61
_reflns_number_total             6205
_reflns_number_gt                5869
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0509P)²+3.1540P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6205
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.62340(5) 0.25653(3) 0.25051(2) 0.02188(11) Uani 1 1 d . . .
C1 C 0.4520(2) 0.24816(11) 0.28876(10) 0.0240(4) Uani 1 1 d . . .
H1 H 0.3770 0.2340 0.2494 0.029 Uiso 1 1 calc R . .
O1 O 0.47158(15) 0.18236(8) 0.33599(7) 0.0258(3) Uani 1 1 d . . .
C2 C 0.3564(2) 0.12416(13) 0.33210(12) 0.0314(4) Uani 1 1 d . . .
H2 H 0.3278 0.1106 0.2808 0.038 Uiso 1 1 calc R . .
C3 C 0.2314(3) 0.15681(18) 0.36427(18) 0.0527(7) Uani 1 1 d . . .
H3A H 0.2595 0.1721 0.4141 0.079 Uiso 1 1 calc R . .
H3B H 0.1572 0.1159 0.3627 0.079 Uiso 1 1 calc R . .
H3C H 0.1953 0.2039 0.3372 0.079 Uiso 1 1 calc R . .
C4 C 0.4190(3) 0.05078(15) 0.37012(17) 0.0507(7) Uani 1 1 d . . .
H4A H 0.4995 0.0318 0.3462 0.076 Uiso 1 1 calc R . .
H4B H 0.3469 0.0087 0.3689 0.076 Uiso 1 1 calc R . .
H4C H 0.4510 0.0643 0.4199 0.076 Uiso 1 1 calc R . .
C5 C 0.4120(2) 0.32641(12) 0.32185(11) 0.0252(4) Uani 1 1 d . . .
C6 C 0.3390(2) 0.38363(13) 0.27813(12) 0.0309(4) Uani 1 1 d . . .
H6 H 0.3113 0.3721 0.2292 0.037 Uiso 1 1 calc R . .
C7 C 0.3070(2) 0.45748(14) 0.30650(13) 0.0365(5) Uani 1 1 d . . .
H7 H 0.2590 0.4968 0.2766 0.044 Uiso 1 1 calc R . .
C8 C 0.3450(2) 0.47407(13) 0.37850(13) 0.0350(5) Uani 1 1 d . . .
H8 H 0.3225 0.5244 0.3979 0.042 Uiso 1 1 calc R . .
C9 C 0.4155(2) 0.41691(13) 0.42152(12) 0.0321(4) Uani 1 1 d . . .
H9 H 0.4408 0.4280 0.4708 0.039 Uiso 1 1 calc R . .
C10 C 0.4500(2) 0.34314(13) 0.39371(11) 0.0279(4) Uani 1 1 d . . .
H10 H 0.4992 0.3043 0.4237 0.034 Uiso 1 1 calc R . .
C11 C 0.7681(2) 0.27145(12) 0.31867(10) 0.0234(4) Uani 1 1 d . . .
C12 C 0.8869(2) 0.31360(13) 0.30061(10) 0.0281(4) Uani 1 1 d . . .
H12 H 0.8894 0.3328 0.2532 0.034 Uiso 1 1 calc R . .
C13 C 1.0001(2) 0.32730(13) 0.35123(11) 0.0291(4) Uani 1 1 d . . .
H13 H 1.0812 0.3552 0.3389 0.035 Uiso 1 1 calc R . .
C14 C 0.9936(2) 0.29964(12) 0.42047(10) 0.0247(4) Uani 1 1 d . . .
Cl1 Cl 1.13309(5) 0.32125(3) 0.48429(3) 0.03486(13) Uani 1 1 d . . .
C15 C 0.8788(2) 0.25661(12) 0.43961(10) 0.0251(4) Uani 1 1 d . . .
H15 H 0.8773 0.2375 0.4871 0.030 Uiso 1 1 calc R . .
C16 C 0.7660(2) 0.24181(11) 0.38828(10) 0.0243(4) Uani 1 1 d . . .
H16 H 0.6872 0.2115 0.4003 0.029 Uiso 1 1 calc R . .
C17 C 0.6505(2) 0.16678(11) 0.20089(9) 0.0217(4) Uani 1 1 d . . .
C18 C 0.5362(2) 0.12111(12) 0.17062(11) 0.0266(4) Uani 1 1 d . . .
H18 H 0.4425 0.1347 0.1797 0.032 Uiso 1 1 calc R . .
C19 C 0.5591(2) 0.05612(12) 0.12747(11) 0.0287(4) Uani 1 1 d . . .
H19 H 0.4819 0.0243 0.1076 0.034 Uiso 1 1 calc R . .
C20 C 0.6965(2) 0.03810(11) 0.11369(10) 0.0255(4) Uani 1 1 d . . .
Cl2 Cl 0.72386(6) -0.04003(3) 0.05638(3) 0.03296(13) Uani 1 1 d . . .
C21 C 0.8108(2) 0.08231(12) 0.14349(10) 0.0260(4) Uani 1 1 d . . .
H21 H 0.9041 0.0687 0.1339 0.031 Uiso 1 1 calc R . .
C22 C 0.7881(2) 0.14670(12) 0.18749(10) 0.0244(4) Uani 1 1 d . . .
H22 H 0.8661 0.1771 0.2085 0.029 Uiso 1 1 calc R . .
C23 C 0.6254(2) 0.34077(12) 0.19098(10) 0.0237(4) Uani 1 1 d . . .
C24 C 0.6439(2) 0.41849(13) 0.21770(12) 0.0325(4) Uani 1 1 d . . .
H24 H 0.6479 0.4279 0.2677 0.039 Uiso 1 1 calc R . .
C25 C 0.6564(3) 0.48155(14) 0.17132(13) 0.0390(5) Uani 1 1 d . . .
H25 H 0.6683 0.5346 0.1891 0.047 Uiso 1 1 calc R . .
C26 C 0.6512(3) 0.46644(13) 0.09817(13) 0.0352(5) Uani 1 1 d . . .
Cl3 Cl 0.67530(8) 0.54442(4) 0.03945(4) 0.05184(18) Uani 1 1 d . . .
C27 C 0.6286(2) 0.39059(13) 0.07101(11) 0.0313(4) Uani 1 1 d . . .
H27 H 0.6221 0.3816 0.0209 0.038 Uiso 1 1 calc R . .
C28 C 0.6155(2) 0.32751(12) 0.11767(10) 0.0263(4) Uani 1 1 d . . .
H28 H 0.5997 0.2749 0.0994 0.032 Uiso 1 1 calc R . .
O2 O 0.13501(19) 0.19017(11) 0.17744(9) 0.0435(4) Uani 1 1 d . . .
O3 O 0.1596(2) 0.16717(10) 0.05140(9) 0.0419(4) Uani 1 1 d . . .
O4 O 0.30359(16) 0.26724(11) 0.11776(9) 0.0389(4) Uani 1 1 d . . .
S S 0.17445(5) 0.22151(3) 0.11079(3) 0.02798(12) Uani 1 1 d . . .
C29 C 0.0400(2) 0.29679(14) 0.08525(12) 0.0335(5) Uani 1 1 d . . .
F1 F 0.06718(17) 0.33564(9) 0.02633(8) 0.0502(4) Uani 1 1 d . . .
F2 F 0.03210(19) 0.35070(10) 0.13695(9) 0.0566(4) Uani 1 1 d . . .
F3 F -0.08777(15) 0.26381(11) 0.07173(10) 0.0557(4) 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
P C11 1.796(2) . ?
P C17 1.7986(19) . ?
P C23 1.800(2) . ?
P C1 1.852(2) . ?
C1 O1 1.413(2) . ?
C1 C5 1.513(3) . ?
C1 H1 1.0000 . ?
O1 C2 1.460(2) . ?
C2 C3 1.491(3) . ?
C2 C4 1.510(3) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.390(3) . ?
C5 C6 1.397(3) . ?
C6 C7 1.390(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.401(3) . ?
C11 C16 1.401(3) . ?
C12 C13 1.378(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 Cl1 1.730(2) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.397(3) . ?
C17 C18 1.398(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(3) . ?
C20 Cl2 1.7294(19) . ?
C21 C22 1.388(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.389(3) . ?
C23 C24 1.397(3) . ?
C24 C25 1.380(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.375(3) . ?
C26 Cl3 1.738(2) . ?
C27 C28 1.385(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
O2 S 1.4430(16) . ?
O3 S 1.4344(16) . ?
O4 S 1.4393(16) . ?
S C29 1.821(2) . ?
C29 F1 1.332(3) . ?
C29 F3 1.333(3) . ?
C29 F2 1.333(3) . ?

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
C11 P C17 110.21(9) . . ?
C11 P C23 106.14(9) . . ?
C17 P C23 108.56(9) . . ?
C11 P C1 111.82(9) . . ?
C17 P C1 108.51(9) . . ?
C23 P C1 111.55(9) . . ?
O1 C1 C5 115.85(16) . . ?
O1 C1 P 103.86(12) . . ?
C5 C1 P 111.27(13) . . ?
O1 C1 H1 108.5 . . ?
C5 C1 H1 108.5 . . ?
P C1 H1 108.5 . . ?
C1 O1 C2 115.98(15) . . ?
O1 C2 C3 111.12(19) . . ?
O1 C2 C4 105.15(18) . . ?
C3 C2 C4 113.3(2) . . ?
O1 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
C4 C2 H2 109.0 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 119.77(19) . . ?
C10 C5 C1 121.51(18) . . ?
C6 C5 C1 118.69(18) . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C9 119.8(2) . . ?
C5 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C16 119.62(18) . . ?
C12 C11 P 118.18(15) . . ?
C16 C11 P 122.19(15) . . ?
C13 C12 C11 120.37(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 118.96(18) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 121.99(18) . . ?
C15 C14 Cl1 119.67(15) . . ?
C13 C14 Cl1 118.34(15) . . ?
C14 C15 C16 118.92(18) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C11 120.09(18) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C22 C17 C18 119.77(17) . . ?
C22 C17 P 118.73(15) . . ?
C18 C17 P 121.27(14) . . ?
C19 C18 C17 120.21(18) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.11(19) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C21 C20 C19 121.45(18) . . ?
C21 C20 Cl2 119.55(15) . . ?
C19 C20 Cl2 118.99(16) . . ?
C20 C21 C22 119.44(18) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C21 C22 C17 120.00(18) . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C28 C23 C24 119.86(18) . . ?
C28 C23 P 119.22(15) . . ?
C24 C23 P 120.84(15) . . ?
C25 C24 C23 119.9(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 119.2(2) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C27 C26 C25 121.4(2) . . ?
C27 C26 Cl3 118.75(18) . . ?
C25 C26 Cl3 119.82(18) . . ?
C26 C27 C28 119.1(2) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C27 C28 C23 120.37(19) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
O3 S O4 114.87(11) . . ?
O3 S O2 115.64(11) . . ?
O4 S O2 114.16(10) . . ?
O3 S C29 102.87(11) . . ?
O4 S C29 102.98(11) . . ?
O2 S C29 103.97(11) . . ?
F1 C29 F3 107.11(19) . . ?
F1 C29 F2 107.91(19) . . ?
F3 C29 F2 107.40(19) . . ?
F1 C29 S 111.39(15) . . ?
F3 C29 S 111.35(16) . . ?
F2 C29 S 111.47(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 P C1 O1 -58.58(14) . . . . ?
C17 P C1 O1 63.18(14) . . . . ?
C23 P C1 O1 -177.28(11) . . . . ?
C11 P C1 C5 66.73(16) . . . . ?
C17 P C1 C5 -171.50(13) . . . . ?
C23 P C1 C5 -51.96(16) . . . . ?
C5 C1 O1 C2 103.30(19) . . . . ?
P C1 O1 C2 -134.37(14) . . . . ?
C1 O1 C2 C3 -73.0(2) . . . . ?
C1 O1 C2 C4 164.05(19) . . . . ?
O1 C1 C5 C10 26.6(3) . . . . ?
P C1 C5 C10 -91.7(2) . . . . ?
O1 C1 C5 C6 -155.31(18) . . . . ?
P C1 C5 C6 86.4(2) . . . . ?
C10 C5 C6 C7 1.2(3) . . . . ?
C1 C5 C6 C7 -176.92(19) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C6 C5 C10 C9 -0.3(3) . . . . ?
C1 C5 C10 C9 177.74(18) . . . . ?
C8 C9 C10 C5 -0.5(3) . . . . ?
C17 P C11 C12 87.78(17) . . . . ?
C23 P C11 C12 -29.58(18) . . . . ?
C1 P C11 C12 -151.44(15) . . . . ?
C17 P C11 C16 -91.60(17) . . . . ?
C23 P C11 C16 151.03(16) . . . . ?
C1 P C11 C16 29.18(19) . . . . ?
C16 C11 C12 C13 -1.3(3) . . . . ?
P C11 C12 C13 179.35(16) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C12 C13 C14 C15 2.1(3) . . . . ?
C12 C13 C14 Cl1 -177.15(16) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
Cl1 C14 C15 C16 178.15(15) . . . . ?
C14 C15 C16 C11 -1.1(3) . . . . ?
C12 C11 C16 C15 2.3(3) . . . . ?
P C11 C16 C15 -178.36(15) . . . . ?
C11 P C17 C22 -36.13(18) . . . . ?
C23 P C17 C22 79.73(17) . . . . ?
C1 P C17 C22 -158.87(15) . . . . ?
C11 P C17 C18 149.42(16) . . . . ?
C23 P C17 C18 -94.72(17) . . . . ?
C1 P C17 C18 26.68(18) . . . . ?
C22 C17 C18 C19 0.0(3) . . . . ?
P C17 C18 C19 174.42(16) . . . . ?
C17 C18 C19 C20 -1.3(3) . . . . ?
C18 C19 C20 C21 1.7(3) . . . . ?
C18 C19 C20 Cl2 -176.90(16) . . . . ?
C19 C20 C21 C22 -0.8(3) . . . . ?
Cl2 C20 C21 C22 177.77(15) . . . . ?
C20 C21 C22 C17 -0.5(3) . . . . ?
C18 C17 C22 C21 0.9(3) . . . . ?
P C17 C22 C21 -173.67(15) . . . . ?
C11 P C23 C28 132.07(16) . . . . ?
C17 P C23 C28 13.61(19) . . . . ?
C1 P C23 C28 -105.90(17) . . . . ?
C11 P C23 C24 -44.69(19) . . . . ?
C17 P C23 C24 -163.15(17) . . . . ?
C1 P C23 C24 77.34(19) . . . . ?
C28 C23 C24 C25 -1.9(3) . . . . ?
P C23 C24 C25 174.88(18) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 C27 2.5(4) . . . . ?
C24 C25 C26 Cl3 -176.88(19) . . . . ?
C25 C26 C27 C28 -2.2(4) . . . . ?
Cl3 C26 C27 C28 177.18(17) . . . . ?
C26 C27 C28 C23 -0.1(3) . . . . ?
C24 C23 C28 C27 2.2(3) . . . . ?
P C23 C28 C27 -174.64(16) . . . . ?
O3 S C29 F1 -63.28(19) . . . . ?
O4 S C29 F1 56.42(18) . . . . ?
O2 S C29 F1 175.77(16) . . . . ?
O3 S C29 F3 56.22(18) . . . . ?
O4 S C29 F3 175.91(16) . . . . ?
O2 S C29 F3 -64.73(18) . . . . ?
O3 S C29 F2 176.14(16) . . . . ?
O4 S C29 F2 -64.17(18) . . . . ?
O2 S C29 F2 55.19(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        76.61
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.119
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.061
