# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_sh5173_a
_database_code_depnum_ccdc_archive 'CCDC 2260785'
loop_
_audit_author_name
_audit_author_address
'Bernd Morgenstern'
;Universitaet des Saarlandes
Germany
;
_audit_update_record             
;
2023-05-05 deposited with the CCDC.	2023-09-08 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         'C16 H36 O4 P, F6 P'
_chemical_formula_sum            'C16 H36 F6 O4 P2'
_chemical_formula_weight         468.39

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'
F F 0.0171 0.0103 '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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.6155(2)
_cell_length_b                   15.4439(4)
_cell_length_c                   15.4444(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.6150(10)
_cell_angle_gamma                90
_cell_volume                     2288.94(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    154(2)
_cell_measurement_reflns_used    4282
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.55

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.256
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7070
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      154(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker X8 Apex, Nonius Kappa CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22277
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.867
_diffrn_reflns_theta_max         27.918
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5485
_reflns_number_gt                4021
_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       'APEX3 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  
;
SHELXL-2018/3 (Sheldrick, 2018),                                              
SHELXLe Rev 1000 (Huebschle et al., 2011)
;
_computing_molecular_graphics    'DIAMOND, Vers. 4.5.3 (Brandenburg, K. 2018)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, G. M.)'
_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)+(0.0326P)²+0.7646P] 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         5485
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.25683(4) 0.40747(3) 0.15230(3) 0.01967(11) Uani 1 1 d . . . . .
O1 O 0.01016(13) 0.19123(8) 0.01432(9) 0.0319(3) Uani 1 1 d . . . . .
O2 O 0.09164(12) 0.47373(8) -0.11544(8) 0.0275(3) Uani 1 1 d . . . . .
O3 O 0.08235(13) 0.59743(9) 0.34392(8) 0.0340(3) Uani 1 1 d . . . . .
O4 O 0.64765(12) 0.42500(8) 0.30599(9) 0.0343(3) Uani 1 1 d . . . . .
C1 C 0.17141(17) 0.30701(11) 0.12462(12) 0.0238(4) Uani 1 1 d . . . . .
H1A H 0.215457 0.281081 0.074502 0.029 Uiso 1 1 calc R U . . .
H1B H 0.185371 0.266541 0.174118 0.029 Uiso 1 1 calc R U . . .
C2 C 0.01492(17) 0.31697(11) 0.10188(13) 0.0270(4) Uani 1 1 d . . . . .
H2A H -0.028937 0.345453 0.150701 0.032 Uiso 1 1 calc R U . . .
H2B H 0.000493 0.354637 0.050228 0.032 Uiso 1 1 calc R U . . .
C3 C -0.05450(18) 0.23096(12) 0.08362(13) 0.0295(4) Uani 1 1 d . . . . .
H3A H -0.044937 0.193733 0.135841 0.035 Uiso 1 1 calc R U . . .
H3B H -0.154986 0.239507 0.067965 0.035 Uiso 1 1 calc R U . . .
C4 C -0.0543(2) 0.11191(13) -0.00933(16) 0.0453(6) Uani 1 1 d . . . . .
H4A H -0.150666 0.122624 -0.031228 0.068 Uiso 1 1 calc R U . . .
H4B H -0.053924 0.073900 0.041488 0.068 Uiso 1 1 calc R U . . .
H4C H -0.003177 0.084118 -0.054695 0.068 Uiso 1 1 calc R U . . .
C5 C 0.22720(17) 0.48249(11) 0.06475(11) 0.0219(4) Uani 1 1 d . . . . .
H5A H 0.125665 0.487602 0.050651 0.026 Uiso 1 1 calc R U . . .
H5B H 0.262228 0.540199 0.083609 0.026 Uiso 1 1 calc R U . . .
C6 C 0.29816(16) 0.45566(12) -0.01688(12) 0.0266(4) Uani 1 1 d . . . . .
H6A H 0.398033 0.471476 -0.010206 0.032 Uiso 1 1 calc R U . . .
H6B H 0.292041 0.391989 -0.023497 0.032 Uiso 1 1 calc R U . . .
C7 C 0.23309(17) 0.49814(13) -0.09757(12) 0.0278(4) Uani 1 1 d . . . . .
H7A H 0.238345 0.561798 -0.090592 0.033 Uiso 1 1 calc R U . . .
H7B H 0.287213 0.482223 -0.147643 0.033 Uiso 1 1 calc R U . . .
C8 C 0.0770(2) 0.38747(12) -0.14681(14) 0.0366(5) Uani 1 1 d . . . . .
H8A H -0.021592 0.375463 -0.162128 0.055 Uiso 1 1 calc R U . . .
H8B H 0.111846 0.346981 -0.101652 0.055 Uiso 1 1 calc R U . . .
H8C H 0.130561 0.380511 -0.198269 0.055 Uiso 1 1 calc R U . . .
C9 C 0.18817(17) 0.45012(11) 0.24882(11) 0.0220(4) Uani 1 1 d . . . . .
H9A H 0.093131 0.472491 0.234095 0.026 Uiso 1 1 calc R U . . .
H9B H 0.180179 0.402320 0.290931 0.026 Uiso 1 1 calc R U . . .
C10 C 0.27580(17) 0.52264(11) 0.29239(11) 0.0249(4) Uani 1 1 d . . . . .
H10A H 0.369926 0.500254 0.309779 0.030 Uiso 1 1 calc R U . . .
H10B H 0.286179 0.570333 0.250454 0.030 Uiso 1 1 calc R U . . .
C11 C 0.20906(19) 0.55698(12) 0.37123(12) 0.0276(4) Uani 1 1 d . . . . .
H11A H 0.191485 0.508905 0.411505 0.033 Uiso 1 1 calc R U . . .
H11B H 0.271895 0.599187 0.402036 0.033 Uiso 1 1 calc R U . . .
C12 C 0.0116(2) 0.62946(14) 0.41515(14) 0.0425(5) Uani 1 1 d . . . . .
H12A H -0.075079 0.657746 0.393760 0.064 Uiso 1 1 calc R U . . .
H12B H 0.071063 0.671431 0.447497 0.064 Uiso 1 1 calc R U . . .
H12C H -0.009969 0.581322 0.453411 0.064 Uiso 1 1 calc R U . . .
C13 C 0.44040(16) 0.38876(11) 0.17093(12) 0.0248(4) Uani 1 1 d . . . . .
H13A H 0.476572 0.364623 0.117385 0.030 Uiso 1 1 calc R U . . .
H13B H 0.487336 0.444981 0.182643 0.030 Uiso 1 1 calc R U . . .
C14 C 0.47892(18) 0.32709(12) 0.24640(13) 0.0294(4) Uani 1 1 d . . . . .
H14A H 0.418441 0.338803 0.294615 0.035 Uiso 1 1 calc R U . . .
H14B H 0.462860 0.266558 0.227191 0.035 Uiso 1 1 calc R U . . .
C15 C 0.62984(19) 0.33830(12) 0.27804(14) 0.0350(5) Uani 1 1 d . . . . .
H15A H 0.653710 0.298065 0.326629 0.042 Uiso 1 1 calc R U . . .
H15B H 0.691437 0.325722 0.230597 0.042 Uiso 1 1 calc R U . . .
C16 C 0.7861(2) 0.44252(16) 0.33815(17) 0.0542(7) Uani 1 1 d . . . . .
H16A H 0.850187 0.431074 0.292617 0.081 Uiso 1 1 calc R U . . .
H16B H 0.810043 0.405245 0.388240 0.081 Uiso 1 1 calc R U . . .
H16C H 0.793766 0.503361 0.355845 0.081 Uiso 1 1 calc R U . . .
P2 P 0.93794(5) 0.78167(3) 0.61299(3) 0.02608(12) Uani 1 1 d . . . . .
F1 F 0.88973(13) 0.81860(8) 0.51963(8) 0.0499(3) Uani 1 1 d . . . . .
F2 F 0.89404(12) 0.68634(7) 0.58211(8) 0.0398(3) Uani 1 1 d . . . . .
F3 F 1.09028(11) 0.76649(7) 0.58112(8) 0.0395(3) Uani 1 1 d . . . . .
F4 F 0.98048(12) 0.87734(7) 0.64366(8) 0.0441(3) Uani 1 1 d . . . . .
F5 F 0.78559(12) 0.79675(8) 0.64513(10) 0.0561(4) Uani 1 1 d . . . . .
F6 F 0.98735(15) 0.74451(9) 0.70585(8) 0.0569(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
P1 C5 1.7898(17) . ?
P1 C9 1.7933(17) . ?
P1 C13 1.7939(16) . ?
P1 C1 1.7945(17) . ?
O1 C4 1.411(2) . ?
O1 C3 1.412(2) . ?
O2 C8 1.421(2) . ?
O2 C7 1.422(2) . ?
O3 C11 1.410(2) . ?
O3 C12 1.418(2) . ?
O4 C15 1.414(2) . ?
O4 C16 1.417(2) . ?
C1 C2 1.531(2) . ?
C2 C3 1.505(2) . ?
C5 C6 1.528(2) . ?
C6 C7 1.509(2) . ?
C9 C10 1.532(2) . ?
C10 C11 1.508(2) . ?
C13 C14 1.532(2) . ?
C14 C15 1.512(2) . ?
P2 F6 1.5894(13) . ?
P2 F3 1.5918(11) . ?
P2 F1 1.5920(13) . ?
P2 F5 1.5932(12) . ?
P2 F2 1.5963(11) . ?
P2 F4 1.5970(12) . ?

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
C5 P1 C9 109.93(8) . . ?
C5 P1 C13 109.49(8) . . ?
C9 P1 C13 109.63(8) . . ?
C5 P1 C1 109.33(8) . . ?
C9 P1 C1 109.19(8) . . ?
C13 P1 C1 109.26(8) . . ?
C4 O1 C3 111.50(15) . . ?
C8 O2 C7 112.82(14) . . ?
C11 O3 C12 111.72(15) . . ?
C15 O4 C16 112.38(15) . . ?
C2 C1 P1 113.34(12) . . ?
C3 C2 C1 111.84(14) . . ?
O1 C3 C2 108.32(14) . . ?
C6 C5 P1 112.94(12) . . ?
C7 C6 C5 112.34(14) . . ?
O2 C7 C6 112.76(14) . . ?
C10 C9 P1 114.37(11) . . ?
C11 C10 C9 111.20(14) . . ?
O3 C11 C10 108.55(15) . . ?
C14 C13 P1 114.23(12) . . ?
C15 C14 C13 110.85(15) . . ?
O4 C15 C14 107.60(15) . . ?
F6 P2 F3 89.84(7) . . ?
F6 P2 F1 179.48(8) . . ?
F3 P2 F1 89.64(7) . . ?
F6 P2 F5 90.00(8) . . ?
F3 P2 F5 179.85(9) . . ?
F1 P2 F5 90.51(8) . . ?
F6 P2 F2 89.71(7) . . ?
F3 P2 F2 90.17(6) . . ?
F1 P2 F2 90.20(7) . . ?
F5 P2 F2 89.82(6) . . ?
F6 P2 F4 90.57(7) . . ?
F3 P2 F4 90.26(6) . . ?
F1 P2 F4 89.53(7) . . ?
F5 P2 F4 89.76(6) . . ?
F2 P2 F4 179.49(7) . . ?

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
C5 P1 C1 C2 -56.61(15) . . . . ?
C9 P1 C1 C2 63.69(15) . . . . ?
C13 P1 C1 C2 -176.42(13) . . . . ?
P1 C1 C2 C3 -176.99(13) . . . . ?
C4 O1 C3 C2 -177.07(16) . . . . ?
C1 C2 C3 O1 -58.5(2) . . . . ?
C9 P1 C5 C6 173.08(12) . . . . ?
C13 P1 C5 C6 52.60(14) . . . . ?
C1 P1 C5 C6 -67.07(14) . . . . ?
P1 C5 C6 C7 159.01(13) . . . . ?
C8 O2 C7 C6 -72.97(19) . . . . ?
C5 C6 C7 O2 -63.1(2) . . . . ?
C5 P1 C9 C10 -74.75(14) . . . . ?
C13 P1 C9 C10 45.64(15) . . . . ?
C1 P1 C9 C10 165.31(12) . . . . ?
P1 C9 C10 C11 178.17(12) . . . . ?
C12 O3 C11 C10 178.46(15) . . . . ?
C9 C10 C11 O3 -65.72(19) . . . . ?
C5 P1 C13 C14 178.46(13) . . . . ?
C9 P1 C13 C14 57.79(15) . . . . ?
C1 P1 C13 C14 -61.83(15) . . . . ?
P1 C13 C14 C15 -160.27(13) . . . . ?
C16 O4 C15 C14 179.31(17) . . . . ?
C13 C14 C15 O4 60.0(2) . . . . ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_5162_a
_database_code_depnum_ccdc_archive 'CCDC 2260786'
loop_
_audit_author_name
_audit_author_address
'Bernd Morgenstern'
;Universitaet des Saarlandes
Germany
;
_audit_update_record             
;
2023-05-05 deposited with the CCDC.	2023-09-08 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         'C20 H44 P, F6 P'
_chemical_formula_sum            'C20 H44 F6 P2'
_chemical_formula_weight         460.49

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           68
_space_group_name_H-M_alt        'C c c a'
_space_group_name_Hall           '-C 2b 2bc'

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

_cell_length_a                   11.1743(8)
_cell_length_b                   23.349(2)
_cell_length_c                   9.9798(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2603.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    1679
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      25.91

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6467
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC I\^A?S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 Venture, Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7677
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.872
_diffrn_reflns_theta_max         26.728
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1382
_reflns_number_gt                939
_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       'APEX 4 (Bruker, 2021)'
_computing_cell_refinement       'SAINT  (Bruker, 2019)'
_computing_data_reduction        'SAINT  (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  
;
SHELXL-2018/3 (Sheldrick, 2018),                                              
SHELXLe Rev 1000 (Huebschle et al., 2011)
;
_computing_molecular_graphics    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, G. M.)'
_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)+(0.0301P)²+2.2142P] 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         1382
_refine_ls_number_parameters     113
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.028
_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 0.500000 0.750000 0.750000 0.0361(3) Uani 1 4 d S T P . .
C1 C 0.4089(2) 0.70567(8) 0.64458(17) 0.0402(5) Uani 1 1 d . . . . .
H1A H 0.352595 0.730575 0.594829 0.048 Uiso 1 1 calc R U . . .
H1B H 0.461252 0.686777 0.577890 0.048 Uiso 1 1 calc R U . . .
C2 C 0.3365(2) 0.65942(8) 0.71716(17) 0.0431(5) Uani 1 1 d . . . . .
H2A H 0.391652 0.633986 0.767022 0.052 Uiso 1 1 calc R U . . .
H2B H 0.282118 0.677739 0.782706 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2634(2) 0.62396(9) 0.61869(19) 0.0472(5) Uani 1 1 d . . . . .
H3A H 0.211825 0.649902 0.565582 0.057 Uiso 1 1 calc R U . . .
H3B H 0.318544 0.604435 0.555898 0.057 Uiso 1 1 calc R U . . .
C4 C 0.1856(2) 0.57948(9) 0.6867(2) 0.0576(6) Uani 1 1 d . . . . .
H4A H 0.134842 0.598554 0.754669 0.069 Uiso 1 1 calc R U . . .
H4B H 0.237447 0.551585 0.733708 0.069 Uiso 1 1 calc R U . . .
C5 C 0.1053(2) 0.54740(11) 0.5875(3) 0.0726(8) Uani 1 1 d . . . . .
H5A H 0.048982 0.574336 0.546338 0.109 Uiso 1 1 calc R U . . .
H5B H 0.060735 0.517504 0.635002 0.109 Uiso 1 1 calc R U . . .
H5C H 0.154872 0.529848 0.517655 0.109 Uiso 1 1 calc R U . . .
P1_1 P 0.5024(12) 0.7459(6) 0.2567(14) 0.0407(12) Uani 0.25 1 d D U P A -1
F1_1 F 0.6154(12) 0.7556(6) 0.3508(17) 0.051(4) Uani 0.25 1 d D U P A -1
F2_1 F 0.5193(15) 0.8074(6) 0.1953(17) 0.089(5) Uani 0.25 1 d D U P A -1
F3_1 F 0.3905(17) 0.7366(9) 0.158(2) 0.066(6) Uani 0.25 1 d D U P A -1
F4_1 F 0.4744(14) 0.6870(5) 0.3269(13) 0.074(4) Uani 0.25 1 d D U P A -1
F5_1 F 0.5908(13) 0.7193(9) 0.1482(14) 0.103(6) Uani 0.25 1 d D U P A -1
F6_1 F 0.4204(12) 0.7777(12) 0.3641(16) 0.069(4) Uani 0.25 1 d D U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.7930(19) 8_466 ?
P1 C1 1.7930(19) 3_656 ?
P1 C1 1.7930(19) 6_565 ?
P1 C1 1.7931(19) . ?
C1 C2 1.531(3) . ?
C2 C3 1.523(3) . ?
C3 C4 1.515(3) . ?
C4 C5 1.532(3) . ?
P1_1 F2_1 1.571(11) . ?
P1_1 F4_1 1.576(10) . ?
P1_1 F1_1 1.590(12) . ?
P1_1 F5_1 1.593(12) . ?
P1_1 F6_1 1.593(12) . ?
P1_1 F3_1 1.606(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C1 108.14(12) 8_466 3_656 ?
C1 P1 C1 109.49(13) 8_466 6_565 ?
C1 P1 C1 110.79(14) 3_656 6_565 ?
C1 P1 C1 110.79(14) 8_466 . ?
C1 P1 C1 109.49(13) 3_656 . ?
C1 P1 C1 108.14(12) 6_565 . ?
C2 C1 P1 115.43(12) . . ?
C3 C2 C1 111.19(15) . . ?
C4 C3 C2 113.05(16) . . ?
C3 C4 C5 112.4(2) . . ?
F2_1 P1_1 F4_1 174.1(15) . . ?
F2_1 P1_1 F1_1 90.3(9) . . ?
F4_1 P1_1 F1_1 91.1(9) . . ?
F2_1 P1_1 F5_1 90.9(10) . . ?
F4_1 P1_1 F5_1 94.9(13) . . ?
F1_1 P1_1 F5_1 88.0(9) . . ?
F2_1 P1_1 F6_1 84.7(15) . . ?
F4_1 P1_1 F6_1 89.6(12) . . ?
F1_1 P1_1 F6_1 89.6(10) . . ?
F5_1 P1_1 F6_1 175.0(17) . . ?
F2_1 P1_1 F3_1 88.8(9) . . ?
F4_1 P1_1 F3_1 89.9(9) . . ?
F1_1 P1_1 F3_1 178.5(14) . . ?
F5_1 P1_1 F3_1 90.8(10) . . ?
F6_1 P1_1 F3_1 91.6(10) . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_TW2109_bm
_database_code_depnum_ccdc_archive 'CCDC 2260790'
loop_
_audit_author_name
_audit_author_address
'Bernd Morgenstern'
;Universitaet des Saarlandes
Germany
;
_audit_update_record             
;
2023-05-05 deposited with the CCDC.	2023-09-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT915_TW2109_bm           
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         37 %     
RESPONSE: The presence of one atom of significantly higher atomic number
than anything else in the structure (i.e. the bromine) allows for an unambiguous
determination of the absolute structure without requiring Friedel opposites.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 O4 P, Br'
_chemical_formula_sum            'C16 H36 Br O4 P'
_chemical_formula_weight         403.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   22.6790(12)
_cell_length_b                   5.6876(3)
_cell_length_c                   8.1653(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.864(5)
_cell_angle_gamma                90
_cell_volume                     1037.66(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    934
_cell_measurement_theta_min      3.3420
_cell_measurement_theta_max      26.7120

_exptl_crystal_description       needles
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    2.071
_shelx_estimated_absorpt_T_min   0.575
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            1722
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0118
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.532
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.714
_diffrn_reflns_point_group_measured_fraction_full 0.714
_reflns_number_total             1309
_reflns_number_gt                1269
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.301
_reflns_Friedel_fraction_max     0.371
_reflns_Friedel_fraction_full    0.371

_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       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  
;
SHELXL-2018/3 (Sheldrick, 2018),                                              
SHELXLe Rev 1000 (Huebschle et al., 2011)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_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)+(0.0238P)²+0.2240P] 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 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.019(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1309
_refine_ls_number_parameters     103
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0479
_refine_ls_wR_factor_gt          0.0471
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.044
_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
Br1 Br 0.500000 0.97540(2) 1.000000 0.03502(16) Uani 1 2 d S T P . .
O1 O 0.33111(11) 0.8350(5) 0.5895(3) 0.0410(6) Uani 1 1 d . . . . .
C1 C 0.45200(14) 0.6805(6) 0.5983(4) 0.0262(7) Uani 1 1 d . . . . .
H1A H 0.476903 0.772018 0.687503 0.031 Uiso 1 1 calc R U . . .
H1B H 0.431517 0.793612 0.515380 0.031 Uiso 1 1 calc R U . . .
P1 P 0.500000 0.4977(3) 0.500000 0.0205(3) Uani 1 2 d S T P . .
C2 C 0.40483(13) 0.5454(6) 0.6729(4) 0.0346(9) Uani 1 1 d . . . . .
H2A H 0.383402 0.436014 0.588831 0.042 Uiso 1 1 calc R U . . .
H2B H 0.424634 0.451206 0.768696 0.042 Uiso 1 1 calc R U . . .
O2 O 0.33477(11) 0.1597(5) 0.2300(3) 0.0430(6) Uani 1 1 d . . . . .
C3 C 0.36058(14) 0.7123(7) 0.7294(4) 0.0354(8) Uani 1 1 d . . . . .
H3A H 0.331192 0.623399 0.781816 0.042 Uiso 1 1 calc R U . . .
H3B H 0.381709 0.824050 0.812242 0.042 Uiso 1 1 calc R U . . .
C5 C 0.45493(14) 0.3140(6) 0.3499(4) 0.0272(7) Uani 1 1 d . . . . .
H5A H 0.481442 0.224551 0.287993 0.033 Uiso 1 1 calc R U . . .
H5B H 0.433314 0.199160 0.408956 0.033 Uiso 1 1 calc R U . . .
C4 C 0.29194(15) 1.0095(9) 0.6317(5) 0.0504(12) Uani 1 1 d . . . . .
H4A H 0.273542 1.093591 0.531076 0.076 Uiso 1 1 calc R U . . .
H4B H 0.314496 1.120759 0.710235 0.076 Uiso 1 1 calc R U . . .
H4C H 0.260633 0.935310 0.683078 0.076 Uiso 1 1 calc R U . . .
C6 C 0.40927(12) 0.4515(9) 0.2256(3) 0.0343(7) Uani 1 1 d . . . . .
H6A H 0.386739 0.560688 0.286406 0.041 Uiso 1 1 calc R U . . .
H6B H 0.430456 0.545822 0.151861 0.041 Uiso 1 1 calc R U . . .
C8 C 0.29947(14) -0.0229(12) 0.1491(4) 0.0505(8) Uani 1 1 d . . . . .
H8A H 0.279786 -0.106918 0.229585 0.076 Uiso 1 1 calc R U . . .
H8B H 0.324921 -0.132166 0.099902 0.076 Uiso 1 1 calc R U . . .
H8C H 0.269080 0.043186 0.061326 0.076 Uiso 1 1 calc R U . . .
C7 C 0.36624(15) 0.2841(7) 0.1222(4) 0.0349(8) Uani 1 1 d . . . . .
H7A H 0.337821 0.372945 0.039219 0.042 Uiso 1 1 calc R U . . .
H7B H 0.388530 0.172875 0.062282 0.042 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
O1 C3 1.406(4) . ?
O1 C4 1.414(5) . ?
C1 C2 1.526(4) . ?
C1 P1 1.791(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
P1 C5 1.791(3) . ?
P1 C5 1.791(3) 2_656 ?
C2 C3 1.510(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O2 C8 1.405(6) . ?
O2 C7 1.414(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.535(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 C7 1.513(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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
C3 O1 C4 112.4(2) . . ?
C2 C1 P1 114.1(2) . . ?
C2 C1 H1A 108.7 . . ?
P1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
P1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C5 P1 C5 108.6(2) . 2_656 ?
C5 P1 C1 109.00(14) . . ?
C5 P1 C1 110.58(15) 2_656 . ?
C5 P1 C1 110.58(15) . 2_656 ?
C5 P1 C1 109.00(14) 2_656 2_656 ?
C1 P1 C1 109.0(2) . 2_656 ?
C3 C2 C1 110.7(3) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C8 O2 C7 112.6(3) . . ?
O1 C3 C2 108.2(3) . . ?
O1 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
O1 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C6 C5 P1 113.4(3) . . ?
C6 C5 H5A 108.9 . . ?
P1 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
P1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C7 C6 C5 110.2(4) . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C7 C6 108.3(3) . . ?
O2 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
O2 C7 H7B 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?

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
C2 C1 P1 C5 53.8(3) . . . . ?
C2 C1 P1 C5 -65.6(3) . . . 2_656 ?
C2 C1 P1 C1 174.6(3) . . . 2_656 ?
P1 C1 C2 C3 -171.3(2) . . . . ?
C4 O1 C3 C2 -175.3(3) . . . . ?
C1 C2 C3 O1 62.0(4) . . . . ?
C5 P1 C5 C6 173.6(3) 2_656 . . . ?
C1 P1 C5 C6 53.1(3) . . . . ?
C1 P1 C5 C6 -66.8(3) 2_656 . . . ?
P1 C5 C6 C7 -170.5(2) . . . . ?
C8 O2 C7 C6 -171.9(4) . . . . ?
C5 C6 C7 O2 61.9(3) . . . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_5209_a
_database_code_depnum_ccdc_archive 'CCDC 2260787'
loop_
_audit_author_name
_audit_author_address
'Bernd Morgenstern'
;Universitaet des Saarlandes
Germany
;
_audit_update_record             
;
2023-05-05 deposited with the CCDC.	2023-09-08 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         'C20 H44 P, B F4'
_chemical_formula_sum            'C20 H44 B F4 P'
_chemical_formula_weight         402.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           54
_space_group_name_H-M_alt        'P c c a'
_space_group_name_Hall           '-P 2a 2ac'

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

_cell_length_a                   23.535(4)
_cell_length_b                   10.8949(17)
_cell_length_c                   9.5632(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2452.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    4694
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.14

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5928
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC I\^A?S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 Venture, Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19707
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.548
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2289
_reflns_number_gt                1757
_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       'APEX 4 (Bruker, 2021)'
_computing_cell_refinement       'SAINT  (Bruker, 2019)'
_computing_data_reduction        'SAINT  (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  
;
SHELXL-2018/3 (Sheldrick, 2018),                                              
SHELXLe Rev 1000 (Huebschle et al., 2011)
;
_computing_molecular_graphics    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, G. M.)'
_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)+(0.0201P)²+3.2134P] 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         2289
_refine_ls_number_parameters     176
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.219
_refine_ls_restrained_S_all      1.203
_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 0.500000 0.75789(10) 0.750000 0.0301(3) Uani 1 2 d S T P . .
C1 C 0.53772(11) 0.6641(3) 0.6264(3) 0.0330(7) Uani 1 1 d . . . . .
H1A H 0.510553 0.606504 0.582357 0.040 Uiso 1 1 calc R U . . .
H1B H 0.553172 0.717512 0.551794 0.040 Uiso 1 1 calc R U . . .
C2 C 0.58672(12) 0.5899(3) 0.6905(3) 0.0336(7) Uani 1 1 d . . . . .
H2A H 0.614273 0.646735 0.734373 0.040 Uiso 1 1 calc R U . . .
H2B H 0.571621 0.535213 0.764315 0.040 Uiso 1 1 calc R U . . .
C3 C 0.61695(11) 0.5131(3) 0.5800(3) 0.0344(7) Uani 1 1 d . . . . .
H3A H 0.589518 0.454439 0.538861 0.041 Uiso 1 1 calc R U . . .
H3B H 0.630342 0.567829 0.504206 0.041 Uiso 1 1 calc R U . . .
C4 C 0.66725(13) 0.4423(3) 0.6381(3) 0.0427(8) Uani 1 1 d . . . . .
H4A H 0.653960 0.388988 0.715322 0.051 Uiso 1 1 calc R U . . .
H4B H 0.695023 0.501152 0.677480 0.051 Uiso 1 1 calc R U . . .
C5 C 0.69680(14) 0.3635(3) 0.5290(3) 0.0511(9) Uani 1 1 d . . . . .
H5A H 0.730227 0.324327 0.570810 0.077 Uiso 1 1 calc R U . . .
H5B H 0.708688 0.415071 0.450367 0.077 Uiso 1 1 calc R U . . .
H5C H 0.670530 0.300144 0.495564 0.077 Uiso 1 1 calc R U . . .
C6 C 0.54904(11) 0.8521(3) 0.8450(3) 0.0333(7) Uani 1 1 d . . . . .
H6A H 0.527061 0.909709 0.904050 0.040 Uiso 1 1 calc R U . . .
H6B H 0.571351 0.798796 0.908356 0.040 Uiso 1 1 calc R U . . .
C7 C 0.59051(11) 0.9267(3) 0.7553(3) 0.0350(6) Uani 1 1 d . . . . .
H7A H 0.612907 0.870366 0.695617 0.042 Uiso 1 1 calc R U . . .
H7B H 0.568866 0.982498 0.693323 0.042 Uiso 1 1 calc R U . . .
C8 C 0.63066(12) 1.0017(3) 0.8467(3) 0.0399(7) Uani 1 1 d . . . . .
H8A H 0.607872 1.055691 0.908285 0.048 Uiso 1 1 calc R U . . .
H8B H 0.652562 0.945138 0.907171 0.048 Uiso 1 1 calc R U . . .
C9 C 0.67181(13) 1.0800(3) 0.7636(3) 0.0481(8) Uani 1 1 d . . . . .
H9A H 0.650091 1.133638 0.699428 0.058 Uiso 1 1 calc R U . . .
H9B H 0.696238 1.025910 0.706142 0.058 Uiso 1 1 calc R U . . .
C10 C 0.70925(15) 1.1593(4) 0.8572(4) 0.0624(11) Uani 1 1 d . . . . .
H10A H 0.735991 1.205901 0.799236 0.094 Uiso 1 1 calc R U . . .
H10B H 0.730433 1.106729 0.921921 0.094 Uiso 1 1 calc R U . . .
H10C H 0.685404 1.216332 0.910431 0.094 Uiso 1 1 calc R U . . .
B1 B 0.500000 0.2410(6) 0.750000 0.0520(14) Uani 1 2 d S T P . .
F1_1 F 0.5562(6) 0.2623(14) 0.703(3) 0.095(9) Uani 0.283(11) 1 d D . P A -1
F2_1 F 0.4791(11) 0.162(2) 0.636(3) 0.071(10) Uani 0.283(11) 1 d D . P A -1
F3_1 F 0.5068(13) 0.153(2) 0.860(3) 0.062(10) Uani 0.283(11) 1 d D . P A -1
F4_1 F 0.4713(9) 0.3268(14) 0.773(3) 0.133(9) Uani 0.283(11) 1 d D . P A -1
F1_2 F 0.5566(6) 0.2626(19) 0.800(2) 0.074(6) Uani 0.217(11) 1 d D . P A -2
F2_2 F 0.4883(12) 0.3700(13) 0.6955(19) 0.075(6) Uani 0.217(11) 1 d D . P A -2
F3_2 F 0.4984(13) 0.172(2) 0.646(2) 0.062(11) Uani 0.217(11) 1 d D . P A -2
F4_2 F 0.4660(10) 0.229(3) 0.8566(14) 0.087(10) Uani 0.217(11) 1 d D . P A -2


_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 C6 1.792(3) 3_656 ?
P1 C6 1.792(3) . ?
P1 C1 1.797(3) . ?
P1 C1 1.797(3) 3_656 ?
C1 C2 1.536(4) . ?
C2 C3 1.524(4) . ?
C3 C4 1.518(4) . ?
C4 C5 1.520(4) . ?
C6 C7 1.533(4) . ?
C7 C8 1.525(4) . ?
C8 C9 1.515(4) . ?
C9 C10 1.524(4) . ?
B1 F4_1 1.175(12) . ?
B1 F3_2 1.244(19) . ?
B1 F4_2 1.301(13) . ?
B1 F1_1 1.414(12) . ?
B1 F3_1 1.43(2) . ?
B1 F1_2 1.433(11) . ?
B1 F2_1 1.48(2) . ?
B1 F2_2 1.524(14) . ?

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 P1 C6 110.1(2) 3_656 . ?
C6 P1 C1 108.08(12) 3_656 . ?
C6 P1 C1 109.94(13) . . ?
C6 P1 C1 109.94(13) 3_656 3_656 ?
C6 P1 C1 108.09(12) . 3_656 ?
C1 P1 C1 110.7(2) . 3_656 ?
C2 C1 P1 114.08(18) . . ?
C3 C2 C1 111.3(2) . . ?
C4 C3 C2 112.9(2) . . ?
C3 C4 C5 113.1(3) . . ?
C7 C6 P1 115.46(19) . . ?
C8 C7 C6 111.0(2) . . ?
C9 C8 C7 113.4(3) . . ?
C8 C9 C10 112.4(3) . . ?
F3_2 B1 F4_2 123.2(15) . . ?
F4_1 B1 F1_1 117.8(14) . . ?
F4_1 B1 F3_1 117.3(14) . . ?
F1_1 B1 F3_1 103.8(13) . . ?
F3_2 B1 F1_2 113.0(14) . . ?
F4_2 B1 F1_2 109.1(7) . . ?
F4_1 B1 F2_1 114.4(15) . . ?
F1_1 B1 F2_1 100.0(11) . . ?
F3_1 B1 F2_1 100.8(10) . . ?
F3_2 B1 F2_2 106.2(12) . . ?
F4_2 B1 F2_2 104.3(13) . . ?
F1_2 B1 F2_2 97.5(10) . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_sh5217_a
_database_code_depnum_ccdc_archive 'CCDC 2260788'
loop_
_audit_author_name
_audit_author_address
'Bernd Morgenstern'
;Universitaet des Saarlandes
Germany
;
_audit_update_record             
;
2023-05-05 deposited with the CCDC.	2023-09-08 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         'C20 H44 P, Br'
_chemical_formula_sum            'C20 H44 Br P'
_chemical_formula_weight         395.43

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.605(2)
_cell_length_b                   14.647(3)
_cell_length_c                   13.946(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.312(6)
_cell_angle_gamma                90
_cell_volume                     2369.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    3265
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      26.75

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.800
_shelx_estimated_absorpt_T_min   0.704
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4829
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC I\^A?S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 Venture, Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20644
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.017
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4158
_reflns_number_gt                2536
_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       'APEX 4 (Bruker, 2021)'
_computing_cell_refinement       'SAINT  (Bruker, 2019)'
_computing_data_reduction        'SAINT  (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  
;
SHELXL-2018/3 (Sheldrick, 2018),                                              
SHELXLe Rev 1000 (Huebschle et al., 2011)
;
_computing_molecular_graphics    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, G. M.)'
_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)+(0.0863P)²+1.9766P] 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         4158
_refine_ls_number_parameters     310
_refine_ls_number_restraints     424
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1779
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.027
_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
Br1 Br 0.52303(6) 0.68072(4) 0.60462(4) 0.0810(3) Uani 1 1 d . . . . .
P1 P 0.43029(11) 0.38990(9) 0.67437(8) 0.0474(3) Uani 1 1 d . . . . .
C1 C 0.3495(4) 0.4662(3) 0.5974(3) 0.0508(12) Uani 1 1 d . . . . .
H1A H 0.394995 0.522795 0.589304 0.061 Uiso 1 1 calc R U . . .
H1B H 0.340352 0.437436 0.533455 0.061 Uiso 1 1 calc R U . . .
C2 C 0.2303(4) 0.4923(3) 0.6327(3) 0.0523(12) Uani 1 1 d . . . . .
H2A H 0.182956 0.436348 0.637793 0.063 Uiso 1 1 calc R U . . .
H2B H 0.238504 0.519222 0.697550 0.063 Uiso 1 1 calc R U . . .
C3 C 0.1682(4) 0.5598(3) 0.5670(4) 0.0562(13) Uani 1 1 d . . . . .
H3A H 0.215182 0.615929 0.562138 0.067 Uiso 1 1 calc R U . . .
H3B H 0.160090 0.533008 0.502031 0.067 Uiso 1 1 calc R U . . .
C4 C 0.0503(4) 0.5844(4) 0.6028(4) 0.0631(14) Uani 1 1 d . . . . .
H4A H 0.058915 0.609344 0.668517 0.076 Uiso 1 1 calc R U . . .
H4B H 0.003485 0.528052 0.606511 0.076 Uiso 1 1 calc R U . . .
C5 C -0.0142(5) 0.6534(4) 0.5406(4) 0.0791(18) Uani 1 1 d . . . . .
H5A H -0.089528 0.665924 0.568155 0.119 Uiso 1 1 calc R U . . .
H5B H 0.030361 0.710131 0.537809 0.119 Uiso 1 1 calc R U . . .
H5C H -0.025148 0.628725 0.475716 0.119 Uiso 1 1 calc R U . . .
C6 C 0.5797(4) 0.4074(4) 0.6532(3) 0.0524(12) Uani 1 1 d D . . . .
H6A H 0.598457 0.381805 0.589697 0.063 Uiso 0.34(3) 1 calc R U P A 1
H6B H 0.595646 0.473806 0.651516 0.063 Uiso 0.34(3) 1 calc R U P A 1
H6C H 0.594193 0.396047 0.584498 0.063 Uiso 0.66(3) 1 calc R U P A 2
H6D H 0.599113 0.472023 0.666809 0.063 Uiso 0.66(3) 1 calc R U P A 2
C7 C 0.660(2) 0.361(3) 0.733(3) 0.064(4) Uani 0.34(3) 1 d D U P A 1
H7A H 0.637074 0.296852 0.742750 0.077 Uiso 0.34(3) 1 calc R U P A 1
H7B H 0.653506 0.394086 0.794679 0.077 Uiso 0.34(3) 1 calc R U P A 1
C8 C 0.789(2) 0.366(4) 0.697(3) 0.066(3) Uani 0.34(3) 1 d D U P A 1
H8A H 0.809396 0.429695 0.679760 0.079 Uiso 0.34(3) 1 calc R U P A 1
H8B H 0.798480 0.326832 0.639787 0.079 Uiso 0.34(3) 1 calc R U P A 1
C9 C 0.866(2) 0.331(2) 0.785(2) 0.069(4) Uani 0.34(3) 1 d D U P A 1
H9A H 0.870095 0.376952 0.836509 0.083 Uiso 0.34(3) 1 calc R U P A 1
H9B H 0.834648 0.273290 0.810876 0.083 Uiso 0.34(3) 1 calc R U P A 1
C10 C 0.989(2) 0.314(2) 0.741(2) 0.078(5) Uani 0.34(3) 1 d D U P A 1
H10A H 1.042475 0.292261 0.791007 0.117 Uiso 0.34(3) 1 calc R U P A 1
H10B H 0.982898 0.269028 0.689292 0.117 Uiso 0.34(3) 1 calc R U P A 1
H10C H 1.018107 0.371996 0.714753 0.117 Uiso 0.34(3) 1 calc R U P A 1
C7B C 0.6587(11) 0.3465(14) 0.7135(14) 0.064(3) Uani 0.66(3) 1 d . U P A 2
H7C H 0.632046 0.346805 0.780459 0.076 Uiso 0.66(3) 1 calc R U P A 2
H7D H 0.652222 0.283090 0.689327 0.076 Uiso 0.66(3) 1 calc R U P A 2
C8B C 0.7829(12) 0.3745(19) 0.7134(14) 0.065(3) Uani 0.66(3) 1 d . U P A 2
H8C H 0.791243 0.433406 0.747539 0.078 Uiso 0.66(3) 1 calc R U P A 2
H8D H 0.805869 0.384306 0.646205 0.078 Uiso 0.66(3) 1 calc R U P A 2
C9B C 0.8640(10) 0.3061(11) 0.7594(11) 0.066(3) Uani 0.66(3) 1 d . U P A 2
H9C H 0.870532 0.251849 0.717513 0.079 Uiso 0.66(3) 1 calc R U P A 2
H9D H 0.833179 0.285921 0.821579 0.079 Uiso 0.66(3) 1 calc R U P A 2
C10B C 0.9883(10) 0.3512(12) 0.7763(12) 0.078(4) Uani 0.66(3) 1 d . U P A 2
H10D H 1.040568 0.306497 0.806210 0.118 Uiso 0.66(3) 1 calc R U P A 2
H10E H 1.018871 0.370455 0.714528 0.118 Uiso 0.66(3) 1 calc R U P A 2
H10F H 0.981598 0.404454 0.818372 0.118 Uiso 0.66(3) 1 calc R U P A 2
C11 C 0.4015(4) 0.4173(3) 0.7975(3) 0.0532(12) Uani 1 1 d D . . . .
H11A H 0.317140 0.419287 0.806311 0.064 Uiso 0.721(8) 1 calc R U P B 1
H11B H 0.433761 0.368865 0.839660 0.064 Uiso 0.721(8) 1 calc R U P B 1
H11C H 0.320264 0.400797 0.808962 0.064 Uiso 0.279(8) 1 calc R U P B 2
H11D H 0.449993 0.376659 0.838241 0.064 Uiso 0.279(8) 1 calc R U P B 2
C12 C 0.4551(9) 0.5112(9) 0.8272(9) 0.068(2) Uani 0.721(8) 1 d D U P B 1
H12A H 0.539021 0.502832 0.838258 0.082 Uiso 0.721(8) 1 calc R U P B 1
H12B H 0.444626 0.554257 0.773004 0.082 Uiso 0.721(8) 1 calc R U P B 1
C13 C 0.4051(8) 0.5541(6) 0.9161(6) 0.074(2) Uani 0.721(8) 1 d D U P B 1
H13A H 0.402235 0.507591 0.967476 0.089 Uiso 0.721(8) 1 calc R U P B 1
H13B H 0.456613 0.603886 0.938706 0.089 Uiso 0.721(8) 1 calc R U P B 1
C14 C 0.2861(8) 0.5919(7) 0.8983(7) 0.093(2) Uani 0.721(8) 1 d D U P B 1
H14A H 0.285815 0.628838 0.838810 0.111 Uiso 0.721(8) 1 calc R U P B 1
H14B H 0.231638 0.540597 0.888133 0.111 Uiso 0.721(8) 1 calc R U P B 1
C15 C 0.2457(11) 0.6493(10) 0.9783(9) 0.121(4) Uani 0.721(8) 1 d D U P B 1
H15A H 0.167981 0.671995 0.962886 0.182 Uiso 0.721(8) 1 calc R U P B 1
H15B H 0.244003 0.612750 1.037111 0.182 Uiso 0.721(8) 1 calc R U P B 1
H15C H 0.298205 0.701030 0.987766 0.182 Uiso 0.721(8) 1 calc R U P B 1
C12B C 0.418(3) 0.506(3) 0.831(3) 0.074(4) Uani 0.279(8) 1 d D U P B 2
H12C H 0.401037 0.549105 0.777812 0.089 Uiso 0.279(8) 1 calc R U P B 2
H12D H 0.499740 0.513655 0.850602 0.089 Uiso 0.279(8) 1 calc R U P B 2
C13B C 0.342(2) 0.5290(14) 0.9153(17) 0.080(3) Uani 0.279(8) 1 d D U P B 2
H13C H 0.259738 0.523230 0.895826 0.096 Uiso 0.279(8) 1 calc R U P B 2
H13D H 0.357875 0.486081 0.968767 0.096 Uiso 0.279(8) 1 calc R U P B 2
C14B C 0.367(2) 0.6262(14) 0.9477(16) 0.088(3) Uani 0.279(8) 1 d D U P B 2
H14C H 0.445525 0.628324 0.977235 0.106 Uiso 0.279(8) 1 calc R U P B 2
H14D H 0.366701 0.666494 0.890714 0.106 Uiso 0.279(8) 1 calc R U P B 2
C15B C 0.283(2) 0.663(2) 1.018(2) 0.106(6) Uani 0.279(8) 1 d D U P B 2
H15D H 0.304473 0.725353 1.035857 0.159 Uiso 0.279(8) 1 calc R U P B 2
H15E H 0.205378 0.662505 0.989082 0.159 Uiso 0.279(8) 1 calc R U P B 2
H15F H 0.284300 0.624287 1.075710 0.159 Uiso 0.279(8) 1 calc R U P B 2
C16 C 0.3961(4) 0.2719(4) 0.6505(4) 0.0577(13) Uani 1 1 d D . . . .
H16A H 0.412899 0.258063 0.582780 0.069 Uiso 0.477(11) 1 calc R U P C 1
H16B H 0.446269 0.232727 0.691489 0.069 Uiso 0.477(11) 1 calc R U P C 1
H16C H 0.428169 0.255883 0.587540 0.069 Uiso 0.523(11) 1 calc R U P C 2
H16D H 0.437077 0.234343 0.699443 0.069 Uiso 0.523(11) 1 calc R U P C 2
C17 C 0.2692(19) 0.2486(18) 0.669(3) 0.102(4) Uani 0.477(11) 1 d D U P C 1
H17A H 0.218459 0.280569 0.622040 0.123 Uiso 0.477(11) 1 calc R U P C 1
H17B H 0.248631 0.269097 0.734263 0.123 Uiso 0.477(11) 1 calc R U P C 1
C18 C 0.2521(14) 0.1447(15) 0.6603(18) 0.116(4) Uani 0.477(11) 1 d D U P C 1
H18A H 0.294390 0.121421 0.604501 0.139 Uiso 0.477(11) 1 calc R U P C 1
H18B H 0.282987 0.114039 0.718674 0.139 Uiso 0.477(11) 1 calc R U P C 1
C19 C 0.1275(14) 0.1244(13) 0.6479(17) 0.131(4) Uani 0.477(11) 1 d D U P C 1
H19A H 0.091075 0.181988 0.625655 0.157 Uiso 0.477(11) 1 calc R U P C 1
H19B H 0.098800 0.113138 0.713125 0.157 Uiso 0.477(11) 1 calc R U P C 1
C20 C 0.0753(18) 0.0490(13) 0.5845(17) 0.153(6) Uani 0.477(11) 1 d D U P C 1
H20A H -0.008817 0.050052 0.588954 0.229 Uiso 0.477(11) 1 calc R U P C 1
H20B H 0.096796 0.059116 0.517769 0.229 Uiso 0.477(11) 1 calc R U P C 1
H20C H 0.104603 -0.010458 0.606158 0.229 Uiso 0.477(11) 1 calc R U P C 1
C17B C 0.2713(19) 0.2443(18) 0.649(3) 0.104(4) Uani 0.523(11) 1 d D U P C 2
H17C H 0.225817 0.289321 0.611284 0.125 Uiso 0.523(11) 1 calc R U P C 2
H17D H 0.242756 0.244797 0.715487 0.125 Uiso 0.523(11) 1 calc R U P C 2
C18B C 0.2525(14) 0.1466(15) 0.6047(15) 0.119(4) Uani 0.523(11) 1 d D U P C 2
H18C H 0.323654 0.131136 0.570408 0.142 Uiso 0.523(11) 1 calc R U P C 2
H18D H 0.247699 0.103444 0.659115 0.142 Uiso 0.523(11) 1 calc R U P C 2
C19B C 0.1536(13) 0.1255(13) 0.5380(13) 0.140(4) Uani 0.523(11) 1 d D U P C 2
H19C H 0.160641 0.065492 0.506056 0.167 Uiso 0.523(11) 1 calc R U P C 2
H19D H 0.138246 0.174216 0.490228 0.167 Uiso 0.523(11) 1 calc R U P C 2
C20B C 0.0685(15) 0.1252(16) 0.6195(15) 0.150(5) Uani 0.523(11) 1 d D U P C 2
H20D H -0.009000 0.112050 0.593791 0.224 Uiso 0.523(11) 1 calc R U P C 2
H20E H 0.090908 0.078198 0.666377 0.224 Uiso 0.523(11) 1 calc R U P C 2
H20F H 0.068891 0.185087 0.650815 0.224 Uiso 0.523(11) 1 calc R U P C 2


_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 C6 1.784(5) . ?
P1 C1 1.798(5) . ?
P1 C11 1.802(5) . ?
P1 C16 1.802(5) . ?
C1 C2 1.527(7) . ?
C2 C3 1.518(6) . ?
C3 C4 1.511(7) . ?
C4 C5 1.518(7) . ?
C6 C7B 1.520(17) . ?
C6 C7 1.59(3) . ?
C7 C8 1.59(3) . ?
C8 C9 1.59(3) . ?
C9 C10 1.59(3) . ?
C7B C8B 1.50(2) . ?
C8B C9B 1.51(2) . ?
C9B C10B 1.60(2) . ?
C11 C12B 1.39(3) . ?
C11 C12 1.561(11) . ?
C12 C13 1.517(9) . ?
C13 C14 1.503(10) . ?
C14 C15 1.482(10) . ?
C12B C13B 1.526(15) . ?
C13B C14B 1.520(15) . ?
C14B C15B 1.500(15) . ?
C16 C17B 1.50(2) . ?
C16 C17 1.540(16) . ?
C17 C18 1.540(14) . ?
C18 C19 1.483(14) . ?
C19 C20 1.531(14) . ?
C17B C18B 1.572(13) . ?
C18B C19B 1.493(13) . ?
C19B C20B 1.522(14) . ?

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 P1 C1 107.9(2) . . ?
C6 P1 C11 109.1(2) . . ?
C1 P1 C11 108.9(2) . . ?
C6 P1 C16 108.5(2) . . ?
C1 P1 C16 112.1(2) . . ?
C11 P1 C16 110.2(2) . . ?
C2 C1 P1 115.2(3) . . ?
C3 C2 C1 112.9(4) . . ?
C4 C3 C2 112.2(4) . . ?
C3 C4 C5 114.2(5) . . ?
C7B C6 P1 113.6(7) . . ?
C7 C6 P1 112.3(13) . . ?
C6 C7 C8 107(3) . . ?
C7 C8 C9 105(4) . . ?
C10 C9 C8 104(3) . . ?
C8B C7B C6 114.0(19) . . ?
C7B C8B C9B 114(2) . . ?
C8B C9B C10B 109.8(17) . . ?
C12B C11 P1 120.0(16) . . ?
C12 C11 P1 111.6(5) . . ?
C13 C12 C11 115.1(8) . . ?
C14 C13 C12 112.6(7) . . ?
C15 C14 C13 113.0(8) . . ?
C11 C12B C13B 113(2) . . ?
C14B C13B C12B 109.2(19) . . ?
C15B C14B C13B 114(2) . . ?
C17B C16 P1 118.0(10) . . ?
C17 C16 P1 112.9(10) . . ?
C16 C17 C18 109.1(16) . . ?
C19 C18 C17 109.4(16) . . ?
C18 C19 C20 125.7(18) . . ?
C16 C17B C18B 112.0(15) . . ?
C19B C18B C17B 122.1(17) . . ?
C18B C19B C20B 92.2(15) . . ?

_refine_diff_density_max         0.652
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.068

