# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_bar56
_database_code_depnum_ccdc_archive 'CCDC 1852085'
_audit_update_record             
;
2018-06-27 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;

# start Validation Reply
_vrf_PLAT334_bar56               
;
PROBLEM: Small Average Benzene  C-C Dist. C8     -C13           1.37 Ang.  
RESPONSE: The small average benzene ring distance is due to large thermal motion.
;
# end Validation Reply

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
1,1-phenylenedioxa-5-phenyl-3,3,7,7-tetrakis(trifluoromethyl)-1-phospha-2,6,8-trioxabicyclo[4.3.2(1,5)]octane
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H11 F12 O5 P'
_chemical_formula_sum            'C20 H11 F12 O5 P'
_chemical_properties_physical    'hygroscopic, air-sensitive'
_exptl_crystal_recrystallization_method 
'crystallized from tetrachloromethane solution'
_chemical_melting_point          423

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         590.26

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/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration .

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'

_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.
;

_cell_length_a                   15.787(9)
_cell_length_b                   10.811(6)
_cell_length_c                   13.977(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.816(7)
_cell_angle_gamma                90
_cell_volume                     2199(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5066
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      21.53
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.319
_exptl_crystal_size_min          0.168
_exptl_absorpt_coefficient_mu    0.260
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9085
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20876
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         25.400
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4023
_reflns_number_gt                3018
_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       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'APEX2 v2014.11-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_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     
'w=1/[σ²(Fo²)+(0.0536P)²+1.3951P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4023
_refine_ls_number_parameters     398
_refine_ls_number_restraints     212
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.007
_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 0.23180(4) 0.60299(6) 0.70564(5) 0.04131(19) Uani 1 1 d . . . . .
O1 O 0.15506(12) 0.62602(17) 0.75892(15) 0.0525(5) Uani 1 1 d . . . . .
O2 O 0.17766(11) 0.48368(16) 0.64483(14) 0.0452(4) Uani 1 1 d . . . . .
O3 O 0.20831(12) 0.73477(16) 0.64759(15) 0.0489(5) Uani 1 1 d . . . . .
O6 O 0.37413(12) 0.46329(17) 0.80021(14) 0.0501(5) Uani 1 1 d . . . . .
O8 O 0.31625(11) 0.59763(15) 0.66368(13) 0.0421(4) Uani 1 1 d . . . . .
F1 F 0.18701(16) 0.24099(17) 0.68614(17) 0.0852(6) Uani 1 1 d . . . . .
F2 F 0.07088(13) 0.28709(19) 0.55272(19) 0.0918(7) Uani 1 1 d . . . . .
F3 F 0.18350(15) 0.19044(17) 0.53793(18) 0.0892(7) Uani 1 1 d . . . . .
F4 F 0.21031(18) 0.5505(2) 0.46091(15) 0.1016(8) Uani 1 1 d . . . . .
F5 F 0.17672(18) 0.3687(2) 0.40608(16) 0.1008(7) Uani 1 1 d . . . . .
F6 F 0.08058(15) 0.4767(3) 0.44138(18) 0.1181(10) Uani 1 1 d . . . . .
F7 F 0.22119(13) 0.39127(17) 0.84844(15) 0.0713(5) Uani 1 1 d . . . . .
F8 F 0.35387(13) 0.40365(19) 0.97038(15) 0.0794(6) Uani 1 1 d . . . . .
F9 F 0.25249(14) 0.5414(2) 0.95697(15) 0.0811(6) Uani 1 1 d . . . . .
F10 F 0.43744(13) 0.6942(2) 0.85139(16) 0.0827(6) Uani 1 1 d . . . . .
F11 F 0.32909(14) 0.74903(19) 0.89687(18) 0.0912(7) Uani 1 1 d . . . . .
F12 F 0.43403(15) 0.6244(2) 0.99034(15) 0.0941(7) Uani 1 1 d . . . . .
C3 C 0.20803(18) 0.4020(2) 0.5836(2) 0.0482(6) Uani 1 1 d . . . . .
C4 C 0.31328(19) 0.3828(3) 0.6248(2) 0.0556(7) Uani 1 1 d . . . . .
H4A H 0.328981 0.306179 0.663815 0.067 Uiso 1 1 calc R U . . .
H4B H 0.331660 0.375219 0.566378 0.067 Uiso 1 1 calc R U . . .
C5 C 0.36652(17) 0.4889(2) 0.6941(2) 0.0443(6) Uani 1 1 d D U . . .
C161 C 0.4631(8) 0.507(3) 0.701(2) 0.049(5) Uani 0.54(3) 1 d D U P A 1
C171 C 0.4807(8) 0.5969(13) 0.6408(14) 0.062(3) Uani 0.54(3) 1 d D U P A 1
H171 H 0.433565 0.647759 0.598421 0.074 Uiso 0.54(3) 1 calc R U P A 1
C181 C 0.5691(9) 0.6112(14) 0.6444(16) 0.071(3) Uani 0.54(3) 1 d D U P A 1
H181 H 0.581093 0.671115 0.603597 0.086 Uiso 0.54(3) 1 calc R U P A 1
C191 C 0.6385(10) 0.538(2) 0.7074(18) 0.068(4) Uani 0.54(3) 1 d D U P A 1
H191 H 0.698089 0.549320 0.711201 0.081 Uiso 0.54(3) 1 calc R U P A 1
C201 C 0.6202(10) 0.4465(17) 0.7656(15) 0.068(4) Uani 0.54(3) 1 d D U P A 1
H201 H 0.667497 0.395687 0.807792 0.082 Uiso 0.54(3) 1 calc R U P A 1
C211 C 0.5318(9) 0.4299(16) 0.7617(13) 0.054(3) Uani 0.54(3) 1 d D U P A 1
H211 H 0.519313 0.367384 0.800012 0.065 Uiso 0.54(3) 1 calc R U P A 1
C162 C 0.4609(8) 0.506(3) 0.690(2) 0.042(5) Uani 0.46(3) 1 d D U P A 2
C172 C 0.4688(10) 0.5690(19) 0.6083(15) 0.063(4) Uani 0.46(3) 1 d D U P A 2
H172 H 0.416147 0.598306 0.555078 0.075 Uiso 0.46(3) 1 calc R U P A 2
C182 C 0.5536(12) 0.590(2) 0.6045(18) 0.081(4) Uani 0.46(3) 1 d D U P A 2
H182 H 0.557535 0.631761 0.548289 0.097 Uiso 0.46(3) 1 calc R U P A 2
C192 C 0.6312(12) 0.549(3) 0.682(2) 0.078(5) Uani 0.46(3) 1 d D U P A 2
H192 H 0.688135 0.563639 0.678850 0.094 Uiso 0.46(3) 1 calc R U P A 2
C202 C 0.6256(10) 0.487(2) 0.7656(16) 0.068(4) Uani 0.46(3) 1 d D U P A 2
H202 H 0.678608 0.458584 0.818773 0.082 Uiso 0.46(3) 1 calc R U P A 2
C212 C 0.5399(10) 0.467(2) 0.7696(14) 0.057(4) Uani 0.46(3) 1 d D U P A 2
H212 H 0.536020 0.426452 0.826564 0.068 Uiso 0.46(3) 1 calc R U P A 2
C7 C 0.32146(17) 0.5460(2) 0.8319(2) 0.0462(6) Uani 1 1 d . . . . .
C8 C 0.10714(17) 0.7347(2) 0.7272(2) 0.0497(7) Uani 1 1 d D . . . .
C9 C 0.03910(19) 0.7809(3) 0.7547(3) 0.0627(8) Uani 1 1 d D . . . .
H9 H 0.017858 0.738100 0.798664 0.075 Uiso 1 1 calc R U . . .
C10 C 0.0035(2) 0.8952(3) 0.7132(3) 0.0758(11) Uani 1 1 d . . . . .
H10 H -0.042964 0.929971 0.729884 0.091 Uiso 1 1 calc R U . . .
C11 C 0.0348(2) 0.9580(3) 0.6486(3) 0.0767(10) Uani 1 1 d . . . . .
H11 H 0.009056 1.034273 0.622404 0.092 Uiso 1 1 calc R U . . .
C12 C 0.1039(2) 0.9111(3) 0.6210(3) 0.0663(9) Uani 1 1 d D . . . .
H12 H 0.125659 0.953371 0.577139 0.080 Uiso 1 1 calc R U . . .
C13 C 0.13772(17) 0.7988(2) 0.6627(2) 0.0496(7) Uani 1 1 d D . . . .
C14 C 0.1613(2) 0.2785(3) 0.5899(3) 0.0604(8) Uani 1 1 d . . . . .
C15 C 0.1684(2) 0.4506(3) 0.4720(3) 0.0670(8) Uani 1 1 d . . . . .
C22 C 0.2863(2) 0.4696(3) 0.9026(2) 0.0596(8) Uani 1 1 d . . . . .
C23 C 0.3812(2) 0.6542(3) 0.8946(2) 0.0612(8) 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 O2 1.5979(19) . ?
P1 O3 1.610(2) . ?
P1 O8 1.6527(18) . ?
P1 O1 1.669(2) . ?
P1 C7 1.887(3) . ?
O1 C8 1.374(3) . ?
O2 C3 1.435(3) . ?
O3 C13 1.395(3) . ?
O6 C7 1.405(3) . ?
O6 C5 1.467(3) . ?
O8 C5 1.389(3) . ?
F1 C14 1.309(4) . ?
F2 C14 1.319(4) . ?
F3 C14 1.325(3) . ?
F4 C15 1.306(4) . ?
F5 C15 1.321(4) . ?
F6 C15 1.314(4) . ?
F7 C22 1.321(4) . ?
F8 C22 1.326(3) . ?
F9 C22 1.334(4) . ?
F10 C23 1.325(4) . ?
F11 C23 1.322(4) . ?
F12 C23 1.314(4) . ?
C3 C15 1.531(4) . ?
C3 C14 1.545(4) . ?
C3 C4 1.547(4) . ?
C4 C5 1.526(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C161 1.505(10) . ?
C5 C162 1.525(9) . ?
C161 C211 1.373(12) . ?
C161 C171 1.378(12) . ?
C171 C181 1.385(10) . ?
C171 H171 0.9300 . ?
C181 C191 1.363(12) . ?
C181 H181 0.9300 . ?
C191 C201 1.379(8) . ?
C191 H191 0.9300 . ?
C201 C211 1.386(11) . ?
C201 H201 0.9300 . ?
C211 H211 0.9300 . ?
C162 C172 1.376(13) . ?
C162 C212 1.377(13) . ?
C172 C182 1.379(12) . ?
C172 H172 0.9300 . ?
C182 C192 1.354(13) . ?
C182 H182 0.9300 . ?
C192 C202 1.382(8) . ?
C192 H192 0.9300 . ?
C202 C212 1.392(12) . ?
C202 H202 0.9300 . ?
C212 H212 0.9300 . ?
C7 C23 1.544(4) . ?
C7 C22 1.547(4) . ?
C8 C13 1.366(4) . ?
C8 C9 1.367(4) . ?
C9 C10 1.388(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(4) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O3 118.37(11) . . ?
O2 P1 O8 96.99(10) . . ?
O3 P1 O8 84.95(9) . . ?
O2 P1 O1 91.53(10) . . ?
O3 P1 O1 91.59(9) . . ?
O8 P1 O1 171.46(10) . . ?
O2 P1 C7 106.64(11) . . ?
O3 P1 C7 134.66(12) . . ?
O8 P1 C7 84.54(11) . . ?
O1 P1 C7 92.43(11) . . ?
C8 O1 P1 112.83(17) . . ?
C3 O2 P1 125.47(16) . . ?
C13 O3 P1 113.82(16) . . ?
C7 O6 C5 111.86(19) . . ?
C5 O8 P1 111.39(15) . . ?
O2 C3 C15 107.3(2) . . ?
O2 C3 C14 102.7(2) . . ?
C15 C3 C14 109.8(3) . . ?
O2 C3 C4 114.8(2) . . ?
C15 C3 C4 112.3(2) . . ?
C14 C3 C4 109.3(2) . . ?
C5 C4 C3 112.5(2) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
O8 C5 O6 106.40(19) . . ?
O8 C5 C161 110.7(10) . . ?
O6 C5 C161 106.3(9) . . ?
O8 C5 C162 109.8(9) . . ?
O6 C5 C162 111.3(9) . . ?
O8 C5 C4 109.4(2) . . ?
O6 C5 C4 108.0(2) . . ?
C161 C5 C4 115.6(15) . . ?
C162 C5 C4 111.7(15) . . ?
C211 C161 C171 120.6(9) . . ?
C211 C161 C5 119.7(11) . . ?
C171 C161 C5 119.6(10) . . ?
C161 C171 C181 119.6(10) . . ?
C161 C171 H171 120.2 . . ?
C181 C171 H171 120.2 . . ?
C191 C181 C171 120.3(10) . . ?
C191 C181 H181 119.8 . . ?
C171 C181 H181 119.8 . . ?
C181 C191 C201 119.9(11) . . ?
C181 C191 H191 120.1 . . ?
C201 C191 H191 120.1 . . ?
C191 C201 C211 120.4(11) . . ?
C191 C201 H201 119.8 . . ?
C211 C201 H201 119.8 . . ?
C161 C211 C201 119.1(11) . . ?
C161 C211 H211 120.4 . . ?
C201 C211 H211 120.4 . . ?
C172 C162 C212 118.6(10) . . ?
C172 C162 C5 119.6(10) . . ?
C212 C162 C5 121.6(12) . . ?
C162 C172 C182 120.9(11) . . ?
C162 C172 H172 119.5 . . ?
C182 C172 H172 119.5 . . ?
C192 C182 C172 120.5(12) . . ?
C192 C182 H182 119.8 . . ?
C172 C182 H182 119.8 . . ?
C182 C192 C202 119.9(13) . . ?
C182 C192 H192 120.0 . . ?
C202 C192 H192 120.0 . . ?
C192 C202 C212 119.5(12) . . ?
C192 C202 H202 120.2 . . ?
C212 C202 H202 120.2 . . ?
C162 C212 C202 120.5(12) . . ?
C162 C212 H212 119.7 . . ?
C202 C212 H212 119.7 . . ?
O6 C7 C23 110.8(2) . . ?
O6 C7 C22 105.3(2) . . ?
C23 C7 C22 109.5(2) . . ?
O6 C7 P1 103.52(17) . . ?
C23 C7 P1 110.8(2) . . ?
C22 C7 P1 116.58(19) . . ?
C13 C8 C9 121.1(3) . . ?
C13 C8 O1 110.8(2) . . ?
C9 C8 O1 128.1(3) . . ?
C8 C9 C10 116.4(3) . . ?
C8 C9 H9 121.8 . . ?
C10 C9 H9 121.8 . . ?
C11 C10 C9 121.7(3) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 121.9(3) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 115.2(3) . . ?
C13 C12 H12 122.4 . . ?
C11 C12 H12 122.4 . . ?
C12 C13 C8 123.7(3) . . ?
C12 C13 O3 125.5(3) . . ?
C8 C13 O3 110.9(2) . . ?
F1 C14 F2 106.5(3) . . ?
F1 C14 F3 107.4(3) . . ?
F2 C14 F3 108.1(3) . . ?
F1 C14 C3 111.2(3) . . ?
F2 C14 C3 112.6(3) . . ?
F3 C14 C3 110.8(2) . . ?
F4 C15 F6 107.6(3) . . ?
F4 C15 F5 106.2(3) . . ?
F6 C15 F5 107.1(3) . . ?
F4 C15 C3 112.3(3) . . ?
F6 C15 C3 111.6(3) . . ?
F5 C15 C3 111.7(3) . . ?
F7 C22 F8 107.3(3) . . ?
F7 C22 F9 107.7(3) . . ?
F8 C22 F9 107.2(3) . . ?
F7 C22 C7 111.6(2) . . ?
F8 C22 C7 110.8(2) . . ?
F9 C22 C7 112.0(3) . . ?
F12 C23 F11 108.7(3) . . ?
F12 C23 F10 105.7(3) . . ?
F11 C23 F10 106.9(3) . . ?
F12 C23 C7 113.5(3) . . ?
F11 C23 C7 110.7(2) . . ?
F10 C23 C7 111.0(2) . . ?

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
O2 P1 O1 C8 -115.33(18) . . . . ?
O3 P1 O1 C8 3.11(18) . . . . ?
C7 P1 O1 C8 137.94(19) . . . . ?
O3 P1 O2 C3 92.7(2) . . . . ?
O8 P1 O2 C3 4.6(2) . . . . ?
O1 P1 O2 C3 -174.7(2) . . . . ?
C7 P1 O2 C3 -81.7(2) . . . . ?
O2 P1 O3 C13 89.63(19) . . . . ?
O8 P1 O3 C13 -175.14(18) . . . . ?
O1 P1 O3 C13 -2.96(18) . . . . ?
C7 P1 O3 C13 -97.9(2) . . . . ?
O2 P1 O8 C5 -61.55(17) . . . . ?
O3 P1 O8 C5 -179.57(17) . . . . ?
C7 P1 O8 C5 44.60(17) . . . . ?
P1 O2 C3 C15 -91.1(2) . . . . ?
P1 O2 C3 C14 153.11(19) . . . . ?
P1 O2 C3 C4 34.5(3) . . . . ?
O2 C3 C4 C5 -22.9(3) . . . . ?
C15 C3 C4 C5 100.1(3) . . . . ?
C14 C3 C4 C5 -137.7(3) . . . . ?
P1 O8 C5 O6 -39.0(2) . . . . ?
P1 O8 C5 C161 -154.1(13) . . . . ?
P1 O8 C5 C162 -159.6(14) . . . . ?
P1 O8 C5 C4 77.4(2) . . . . ?
C7 O6 C5 O8 6.4(3) . . . . ?
C7 O6 C5 C161 124.4(14) . . . . ?
C7 O6 C5 C162 126.0(14) . . . . ?
C7 O6 C5 C4 -111.0(2) . . . . ?
C3 C4 C5 O8 -29.5(3) . . . . ?
C3 C4 C5 O6 86.0(3) . . . . ?
C3 C4 C5 C161 -155.2(6) . . . . ?
C3 C4 C5 C162 -151.3(6) . . . . ?
O8 C5 C161 C211 157(2) . . . . ?
O6 C5 C161 C211 42(3) . . . . ?
C4 C5 C161 C211 -78(3) . . . . ?
O8 C5 C161 C171 -26(3) . . . . ?
O6 C5 C161 C171 -141(2) . . . . ?
C4 C5 C161 C171 99(3) . . . . ?
C211 C161 C171 C181 -1(4) . . . . ?
C5 C161 C171 C181 -178.1(18) . . . . ?
C161 C171 C181 C191 -1(3) . . . . ?
C171 C181 C191 C201 2(3) . . . . ?
C181 C191 C201 C211 -1(3) . . . . ?
C171 C161 C211 C201 2(4) . . . . ?
C5 C161 C211 C201 179.0(19) . . . . ?
C191 C201 C211 C161 -1(3) . . . . ?
O8 C5 C162 C172 -41(3) . . . . ?
O6 C5 C162 C172 -158(2) . . . . ?
C4 C5 C162 C172 81(3) . . . . ?
O8 C5 C162 C212 134(3) . . . . ?
O6 C5 C162 C212 17(3) . . . . ?
C4 C5 C162 C212 -104(3) . . . . ?
C212 C162 C172 C182 2(4) . . . . ?
C5 C162 C172 C182 177(2) . . . . ?
C162 C172 C182 C192 -1(3) . . . . ?
C172 C182 C192 C202 0(4) . . . . ?
C182 C192 C202 C212 0(4) . . . . ?
C172 C162 C212 C202 -2(4) . . . . ?
C5 C162 C212 C202 -178(2) . . . . ?
C192 C202 C212 C162 2(4) . . . . ?
C5 O6 C7 C23 -96.0(3) . . . . ?
C5 O6 C7 C22 145.7(2) . . . . ?
C5 O6 C7 P1 22.8(2) . . . . ?
O2 P1 C7 O6 58.36(18) . . . . ?
O3 P1 C7 O6 -114.68(18) . . . . ?
O8 P1 C7 O6 -37.32(16) . . . . ?
O1 P1 C7 O6 150.68(17) . . . . ?
O2 P1 C7 C23 177.19(18) . . . . ?
O3 P1 C7 C23 4.1(3) . . . . ?
O8 P1 C7 C23 81.51(19) . . . . ?
O1 P1 C7 C23 -90.5(2) . . . . ?
O2 P1 C7 C22 -56.7(2) . . . . ?
O3 P1 C7 C22 130.2(2) . . . . ?
O8 P1 C7 C22 -152.4(2) . . . . ?
O1 P1 C7 C22 35.6(2) . . . . ?
P1 O1 C8 C13 -2.4(3) . . . . ?
P1 O1 C8 C9 179.2(2) . . . . ?
C13 C8 C9 C10 0.1(4) . . . . ?
O1 C8 C9 C10 178.4(3) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C10 C11 C12 -0.1(6) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C11 C12 C13 C8 0.0(5) . . . . ?
C11 C12 C13 O3 -178.7(3) . . . . ?
C9 C8 C13 C12 -0.1(5) . . . . ?
O1 C8 C13 C12 -178.6(3) . . . . ?
C9 C8 C13 O3 178.8(2) . . . . ?
O1 C8 C13 O3 0.3(3) . . . . ?
P1 O3 C13 C12 -179.0(2) . . . . ?
P1 O3 C13 C8 2.1(3) . . . . ?
O2 C3 C14 F1 -59.7(3) . . . . ?
C15 C3 C14 F1 -173.6(3) . . . . ?
C4 C3 C14 F1 62.7(3) . . . . ?
O2 C3 C14 F2 59.8(3) . . . . ?
C15 C3 C14 F2 -54.2(3) . . . . ?
C4 C3 C14 F2 -177.9(3) . . . . ?
O2 C3 C14 F3 -179.0(2) . . . . ?
C15 C3 C14 F3 67.1(3) . . . . ?
C4 C3 C14 F3 -56.6(3) . . . . ?
O2 C3 C15 F4 73.6(3) . . . . ?
C14 C3 C15 F4 -175.4(3) . . . . ?
C4 C3 C15 F4 -53.5(4) . . . . ?
O2 C3 C15 F6 -47.3(3) . . . . ?
C14 C3 C15 F6 63.7(4) . . . . ?
C4 C3 C15 F6 -174.4(3) . . . . ?
O2 C3 C15 F5 -167.2(2) . . . . ?
C14 C3 C15 F5 -56.2(3) . . . . ?
C4 C3 C15 F5 65.7(3) . . . . ?
O6 C7 C22 F7 -73.0(3) . . . . ?
C23 C7 C22 F7 167.8(2) . . . . ?
P1 C7 C22 F7 41.1(3) . . . . ?
O6 C7 C22 F8 46.4(3) . . . . ?
C23 C7 C22 F8 -72.8(3) . . . . ?
P1 C7 C22 F8 160.5(2) . . . . ?
O6 C7 C22 F9 166.1(2) . . . . ?
C23 C7 C22 F9 46.9(3) . . . . ?
P1 C7 C22 F9 -79.8(3) . . . . ?
O6 C7 C23 F12 -76.8(3) . . . . ?
C22 C7 C23 F12 39.0(3) . . . . ?
P1 C7 C23 F12 168.9(2) . . . . ?
O6 C7 C23 F11 160.7(2) . . . . ?
C22 C7 C23 F11 -83.5(3) . . . . ?
P1 C7 C23 F11 46.4(3) . . . . ?
O6 C7 C23 F10 42.2(3) . . . . ?
C22 C7 C23 F10 157.9(2) . . . . ?
P1 C7 C23 F10 -72.1(3) . . . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_khas63
_database_code_depnum_ccdc_archive 'CCDC 1852088'
_audit_update_record             
;
2018-06-27 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;

# start Validation Reply
_vrf_PLAT334_khas63              
;
PROBLEM: Small Average Benzene  C-C Dist. C3A    -C7A           1.37 Ang.  
RESPONSE: The small average benzene ring distance is due to large thermal motion.
;
# end Validation Reply

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'triethylammonium oxabenzo-1,3,2-dioxaphosphol-2-oate'
_chemical_name_common            ?
_chemical_formula_moiety         'C6 H16 N 1+, C6 H4 O4 P 1-'
_chemical_formula_sum            'C12 H20 N O4 P'
_exptl_crystal_recrystallization_method 
'crystallized from diethyl ether solution'
_chemical_melting_point          402

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         273.26

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_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.
;

_cell_length_a                   7.266(3)
_cell_length_b                   11.409(5)
_cell_length_c                   8.573(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.695(6)
_cell_angle_gamma                90
_cell_volume                     705.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1105
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      20.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.487
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    0.201
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9182
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5170
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.392
_diffrn_reflns_theta_max         25.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2545
_reflns_number_gt                2011
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.978

_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       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'APEX2 v2014.11-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_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     
'w=1/[σ²(Fo²)+(0.0341P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 727 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_number_reflns         2545
_refine_ls_number_parameters     228
_refine_ls_number_restraints     200
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.031
_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
P2 P 0.61773(13) 0.47242(10) 0.22968(11) 0.0495(3) Uani 1 1 d . . . . .
O1 O 0.6038(4) 0.5884(3) 0.1167(3) 0.0539(8) Uani 1 1 d . . . . .
O2 O 0.5453(4) 0.5046(3) 0.3759(3) 0.0745(11) Uani 1 1 d . . . . .
O3 O 0.8449(3) 0.4693(3) 0.2584(3) 0.0556(7) Uani 1 1 d . . . . .
O4 O 0.5486(5) 0.3702(3) 0.1430(4) 0.0851(12) Uani 1 1 d . . . . .
C3A C 0.9155(5) 0.5526(4) 0.1645(5) 0.0462(10) Uani 1 1 d D . . . .
C4 C 1.0975(5) 0.5685(5) 0.1447(5) 0.0605(12) Uani 1 1 d D . . . .
H4 H 1.189844 0.521798 0.197045 0.073 Uiso 1 1 calc R U . . .
C5 C 1.1391(7) 0.6564(5) 0.0441(6) 0.0695(14) Uani 1 1 d . . . . .
H5 H 1.262044 0.668949 0.028198 0.083 Uiso 1 1 calc R U . . .
C6 C 1.0029(8) 0.7261(5) -0.0336(6) 0.0637(14) Uani 1 1 d . . . . .
H6 H 1.035197 0.785700 -0.099144 0.076 Uiso 1 1 calc R U . . .
C7 C 0.8189(6) 0.7080(4) -0.0147(5) 0.0566(12) Uani 1 1 d . . . . .
H7 H 0.725686 0.753936 -0.067298 0.068 Uiso 1 1 calc R U . . .
C7A C 0.7787(5) 0.6197(3) 0.0846(4) 0.0417(10) Uani 1 1 d . . . . .
N1 N 0.4059(6) 0.4375(3) 0.6364(5) 0.0642(11) Uani 1 1 d D U . . .
C8 C 0.2364(15) 0.3630(10) 0.5987(14) 0.091(3) Uani 0.631(9) 1 d D U P A 1
H8A H 0.131285 0.412689 0.563506 0.109 Uiso 0.631(9) 1 calc R U P A 1
H8B H 0.209320 0.322328 0.692697 0.109 Uiso 0.631(9) 1 calc R U P A 1
C9 C 0.264(4) 0.275(3) 0.473(3) 0.093(5) Uani 0.631(9) 1 d D U P A 1
H9A H 0.343812 0.307439 0.402181 0.140 Uiso 0.631(9) 1 calc R U P A 1
H9B H 0.146297 0.255762 0.415359 0.140 Uiso 0.631(9) 1 calc R U P A 1
H9C H 0.319349 0.205160 0.520133 0.140 Uiso 0.631(9) 1 calc R U P A 1
C10 C 0.3720(19) 0.5465(9) 0.7211(12) 0.104(4) Uani 0.631(9) 1 d D U P A 1
H10A H 0.312805 0.526257 0.813226 0.125 Uiso 0.631(9) 1 calc R U P A 1
H10B H 0.490637 0.581916 0.757354 0.125 Uiso 0.631(9) 1 calc R U P A 1
C11 C 0.257(5) 0.6343(17) 0.630(3) 0.098(6) Uani 0.631(9) 1 d D U P A 1
H11A H 0.297983 0.642789 0.528246 0.147 Uiso 0.631(9) 1 calc R U P A 1
H11B H 0.267524 0.708146 0.684038 0.147 Uiso 0.631(9) 1 calc R U P A 1
H11C H 0.129810 0.609304 0.618474 0.147 Uiso 0.631(9) 1 calc R U P A 1
C12 C 0.5600(13) 0.3671(11) 0.7324(11) 0.089(3) Uani 0.631(9) 1 d D U P A 1
H12A H 0.542128 0.369002 0.842799 0.107 Uiso 0.631(9) 1 calc R U P A 1
H12B H 0.555221 0.285973 0.698175 0.107 Uiso 0.631(9) 1 calc R U P A 1
C13 C 0.7458(18) 0.419(4) 0.710(3) 0.109(7) Uani 0.631(9) 1 d D U P A 1
H13A H 0.730329 0.476604 0.627510 0.163 Uiso 0.631(9) 1 calc R U P A 1
H13B H 0.827357 0.358458 0.682344 0.163 Uiso 0.631(9) 1 calc R U P A 1
H13C H 0.797981 0.456033 0.805799 0.163 Uiso 0.631(9) 1 calc R U P A 1
C8' C 0.353(3) 0.3141(14) 0.626(2) 0.096(5) Uani 0.369(9) 1 d D U P A 2
H8C H 0.299424 0.294197 0.721420 0.116 Uiso 0.369(9) 1 calc R U P A 2
H8D H 0.464746 0.268145 0.625647 0.116 Uiso 0.369(9) 1 calc R U P A 2
C9' C 0.220(7) 0.276(5) 0.491(5) 0.126(14) Uani 0.369(9) 1 d D U P A 2
H9D H 0.137886 0.339032 0.457541 0.190 Uiso 0.369(9) 1 calc R U P A 2
H9E H 0.149740 0.210156 0.521353 0.190 Uiso 0.369(9) 1 calc R U P A 2
H9F H 0.287553 0.252976 0.405602 0.190 Uiso 0.369(9) 1 calc R U P A 2
C10' C 0.229(2) 0.5145(15) 0.638(3) 0.098(5) Uani 0.369(9) 1 d D U P A 2
H10C H 0.127222 0.477173 0.573259 0.117 Uiso 0.369(9) 1 calc R U P A 2
H10D H 0.197107 0.518856 0.744123 0.117 Uiso 0.369(9) 1 calc R U P A 2
C11' C 0.253(9) 0.634(3) 0.579(5) 0.103(10) Uani 0.369(9) 1 d D U P A 2
H11D H 0.356381 0.670568 0.640135 0.155 Uiso 0.369(9) 1 calc R U P A 2
H11E H 0.142702 0.678520 0.587754 0.155 Uiso 0.369(9) 1 calc R U P A 2
H11F H 0.275505 0.630565 0.470986 0.155 Uiso 0.369(9) 1 calc R U P A 2
C12' C 0.553(2) 0.471(2) 0.7636(14) 0.101(5) Uani 0.369(9) 1 d D U P A 2
H12C H 0.517805 0.442882 0.862574 0.122 Uiso 0.369(9) 1 calc R U P A 2
H12D H 0.557573 0.556225 0.769472 0.122 Uiso 0.369(9) 1 calc R U P A 2
C13' C 0.743(3) 0.427(6) 0.746(6) 0.100(9) Uani 0.369(9) 1 d D U P A 2
H13D H 0.776996 0.367100 0.822617 0.150 Uiso 0.369(9) 1 calc R U P A 2
H13E H 0.830560 0.490257 0.760505 0.150 Uiso 0.369(9) 1 calc R U P A 2
H13F H 0.744854 0.394617 0.642332 0.150 Uiso 0.369(9) 1 calc R U P A 2
H1 H 0.447(5) 0.458(4) 0.542(5) 0.065(12) Uiso 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
P2 O4 1.442(4) . ?
P2 O2 1.462(3) . ?
P2 O1 1.636(3) . ?
P2 O3 1.641(3) . ?
O1 C7A 1.378(4) . ?
O3 C3A 1.382(5) . ?
C3A C4 1.365(5) . ?
C3A C7A 1.373(5) . ?
C4 C5 1.380(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(6) . ?
C6 H6 0.9300 . ?
C7 C7A 1.372(6) . ?
C7 H7 0.9300 . ?
N1 C8' 1.460(15) . ?
N1 C10 1.475(9) . ?
N1 C12' 1.485(13) . ?
N1 C8 1.500(10) . ?
N1 C12 1.537(9) . ?
N1 C10' 1.556(14) . ?
N1 H1 0.92(4) . ?
C8 C9 1.51(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.47(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.51(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C8' C9' 1.48(3) . ?
C8' H8C 0.9700 . ?
C8' H8D 0.9700 . ?
C9' H9D 0.9600 . ?
C9' H9E 0.9600 . ?
C9' H9F 0.9600 . ?
C10' C11' 1.47(3) . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C11' H11D 0.9600 . ?
C11' H11E 0.9600 . ?
C11' H11F 0.9600 . ?
C12' C13' 1.50(3) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 P2 O2 120.4(2) . . ?
O4 P2 O1 110.85(17) . . ?
O2 P2 O1 107.5(2) . . ?
O4 P2 O3 110.1(2) . . ?
O2 P2 O3 109.48(17) . . ?
O1 P2 O3 95.62(16) . . ?
C7A O1 P2 109.5(2) . . ?
C3A O3 P2 109.4(2) . . ?
C4 C3A C7A 121.3(4) . . ?
C4 C3A O3 126.5(4) . . ?
C7A C3A O3 112.2(3) . . ?
C3A C4 C5 117.4(4) . . ?
C3A C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
C6 C5 C4 121.6(5) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.5(5) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C7A C7 C6 117.4(4) . . ?
C7A C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C7 C7A C3A 121.7(4) . . ?
C7 C7A O1 125.6(4) . . ?
C3A C7A O1 112.7(3) . . ?
C8' N1 C12' 117.2(13) . . ?
C10 N1 C8 113.8(7) . . ?
C10 N1 C12 109.3(7) . . ?
C8 N1 C12 110.3(7) . . ?
C8' N1 C10' 109.4(12) . . ?
C12' N1 C10' 111.8(11) . . ?
C8' N1 H1 108(3) . . ?
C10 N1 H1 108(3) . . ?
C12' N1 H1 107(2) . . ?
C8 N1 H1 107(3) . . ?
C12 N1 H1 108(2) . . ?
C10' N1 H1 102(3) . . ?
N1 C8 C9 111.0(12) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N1 115.5(13) . . ?
C11 C10 H10A 108.4 . . ?
N1 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
N1 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N1 109.4(15) . . ?
C13 C12 H12A 109.8 . . ?
N1 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
N1 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C8' C9' 118(3) . . ?
N1 C8' H8C 107.7 . . ?
C9' C8' H8C 107.7 . . ?
N1 C8' H8D 107.7 . . ?
C9' C8' H8D 107.7 . . ?
H8C C8' H8D 107.1 . . ?
C8' C9' H9D 109.5 . . ?
C8' C9' H9E 109.5 . . ?
H9D C9' H9E 109.5 . . ?
C8' C9' H9F 109.5 . . ?
H9D C9' H9F 109.5 . . ?
H9E C9' H9F 109.5 . . ?
C11' C10' N1 113(2) . . ?
C11' C10' H10C 109.0 . . ?
N1 C10' H10C 109.0 . . ?
C11' C10' H10D 109.0 . . ?
N1 C10' H10D 109.0 . . ?
H10C C10' H10D 107.8 . . ?
C10' C11' H11D 109.5 . . ?
C10' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C10' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
N1 C12' C13' 115(2) . . ?
N1 C12' H12C 108.4 . . ?
C13' C12' H12C 108.4 . . ?
N1 C12' H12D 108.4 . . ?
C13' C12' H12D 108.4 . . ?
H12C C12' H12D 107.5 . . ?
C12' C13' H13D 109.5 . . ?
C12' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C12' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 P2 O1 C7A -107.3(3) . . . . ?
O2 P2 O1 C7A 119.2(3) . . . . ?
O3 P2 O1 C7A 6.7(3) . . . . ?
O4 P2 O3 C3A 107.9(3) . . . . ?
O2 P2 O3 C3A -117.5(3) . . . . ?
O1 P2 O3 C3A -6.7(3) . . . . ?
P2 O3 C3A C4 -173.3(3) . . . . ?
P2 O3 C3A C7A 4.9(4) . . . . ?
C7A C3A C4 C5 1.5(6) . . . . ?
O3 C3A C4 C5 179.4(4) . . . . ?
C3A C4 C5 C6 0.2(7) . . . . ?
C4 C5 C6 C7 -1.3(8) . . . . ?
C5 C6 C7 C7A 0.7(7) . . . . ?
C6 C7 C7A C3A 1.0(6) . . . . ?
C6 C7 C7A O1 -179.4(4) . . . . ?
C4 C3A C7A C7 -2.1(6) . . . . ?
O3 C3A C7A C7 179.7(4) . . . . ?
C4 C3A C7A O1 178.3(4) . . . . ?
O3 C3A C7A O1 0.0(5) . . . . ?
P2 O1 C7A C7 175.5(3) . . . . ?
P2 O1 C7A C3A -4.9(4) . . . . ?
C10 N1 C8 C9 162.6(16) . . . . ?
C12 N1 C8 C9 -74.1(17) . . . . ?
C8 N1 C10 C11 -68.4(19) . . . . ?
C12 N1 C10 C11 167.8(17) . . . . ?
C10 N1 C12 C13 -78.6(16) . . . . ?
C8 N1 C12 C13 155.6(15) . . . . ?
C12' N1 C8' C9' -174(3) . . . . ?
C10' N1 C8' C9' 58(3) . . . . ?
C8' N1 C10' C11' -155(3) . . . . ?
C12' N1 C10' C11' 74(3) . . . . ?
C8' N1 C12' C13' 69(4) . . . . ?
C10' N1 C12' C13' -164(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.92(4) 1.75(4) 2.670(5) 174(4) . yes

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.030

####################################################################### 
# 
# 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_miron2018_8
_database_code_depnum_ccdc_archive 'CCDC 1852089'
_audit_update_record             
;
2018-06-27 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        '2-hydroxyphenyl phosphoric acid'
_chemical_name_common            ?
_chemical_formula_moiety         'C6 H7 O5 P'
_chemical_formula_sum            'C6 H7 O5 P'
_chemical_melting_point          409

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         190.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_chemical_absolute_configuration ad

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

_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.
;

_cell_length_a                   4.6005(4)
_cell_length_b                   10.1220(8)
_cell_length_c                   16.4334(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     765.24(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2032
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      31.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.457
_exptl_crystal_size_min          0.391
_exptl_absorpt_coefficient_mu    0.338
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6153
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5805
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.193
_diffrn_reflns_theta_max         31.430
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             2368
_reflns_number_gt                2159
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.598
_reflns_Friedel_fraction_max     0.859
_reflns_Friedel_fraction_full    0.943

_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 v2015.9-0 (Bruker AXS)'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'APEX3 v2015.9-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_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     
'w=1/[σ²(Fo²)+(0.0398P)²+0.1231P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 734 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(8)
_refine_ls_number_reflns         2368
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.56581(14) 0.43335(5) 0.53586(3) 0.01326(14) Uani 1 1 d . . . . .
O1 O 0.6638(4) 0.54482(14) 0.59684(10) 0.0155(3) Uani 1 1 d . . . . .
O2 O 0.3901(5) 0.77841(15) 0.54424(10) 0.0180(4) Uani 1 1 d . . . . .
H2 H 0.525(9) 0.747(3) 0.528(2) 0.033(10) Uiso 1 1 d . . . . .
O3 O 0.3342(4) 0.49174(16) 0.47840(10) 0.0174(4) Uani 1 1 d . . . . .
H3 H 0.172(10) 0.460(4) 0.481(2) 0.048(12) Uiso 1 1 d . . . . .
O4 O 0.4276(5) 0.32507(15) 0.58942(10) 0.0205(4) Uani 1 1 d . . . . .
H4 H 0.375(9) 0.259(3) 0.567(2) 0.042(10) Uiso 1 1 d . . . . .
O5 O 0.8281(4) 0.39093(15) 0.48981(11) 0.0203(4) Uani 1 1 d . . . . .
C1 C 0.4584(6) 0.60862(19) 0.64688(12) 0.0141(4) Uani 1 1 d . . . . .
C2 C 0.3334(6) 0.7256(2) 0.61976(12) 0.0143(4) Uani 1 1 d . . . . .
C3 C 0.1377(6) 0.7907(2) 0.66983(14) 0.0200(5) Uani 1 1 d . . . . .
H3A H 0.047152 0.869762 0.651682 0.024 Uiso 1 1 calc R U . . .
C4 C 0.0739(7) 0.7408(2) 0.74623(15) 0.0257(6) Uani 1 1 d . . . . .
H4A H -0.060246 0.785847 0.780312 0.031 Uiso 1 1 calc R U . . .
C5 C 0.2044(8) 0.6258(2) 0.77322(15) 0.0269(6) Uani 1 1 d . . . . .
H5A H 0.160660 0.592612 0.825899 0.032 Uiso 1 1 calc R U . . .
C6 C 0.3980(6) 0.5589(2) 0.72391(14) 0.0221(5) Uani 1 1 d . . . . .
H6A H 0.488686 0.480083 0.742377 0.027 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O5 1.4876(19) . ?
P1 O3 1.5414(19) . ?
P1 O4 1.5429(18) . ?
P1 O1 1.5750(15) . ?
O1 C1 1.410(3) . ?
O2 C2 1.376(3) . ?
O2 H2 0.75(4) . ?
O3 H3 0.82(4) . ?
O4 H4 0.80(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.390(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.385(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.383(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.382(4) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?

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
O5 P1 O3 111.08(10) . . ?
O5 P1 O4 114.81(10) . . ?
O3 P1 O4 109.69(12) . . ?
O5 P1 O1 107.35(10) . . ?
O3 P1 O1 108.24(9) . . ?
O4 P1 O1 105.30(9) . . ?
C1 O1 P1 120.49(16) . . ?
C2 O2 H2 108(2) . . ?
P1 O3 H3 117(3) . . ?
P1 O4 H4 117(2) . . ?
C2 C1 C6 121.2(2) . . ?
C2 C1 O1 118.74(19) . . ?
C6 C1 O1 119.9(2) . . ?
O2 C2 C3 118.2(2) . . ?
O2 C2 C1 122.8(2) . . ?
C3 C2 C1 118.9(2) . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 H6A 120.5 . . ?
C1 C6 H6A 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 P1 O1 C1 177.41(15) . . . . ?
O3 P1 O1 C1 57.43(17) . . . . ?
O4 P1 O1 C1 -59.83(17) . . . . ?
P1 O1 C1 C2 -93.3(2) . . . . ?
P1 O1 C1 C6 90.7(2) . . . . ?
C6 C1 C2 O2 179.4(2) . . . . ?
O1 C1 C2 O2 3.5(4) . . . . ?
C6 C1 C2 C3 -2.2(4) . . . . ?
O1 C1 C2 C3 -178.1(2) . . . . ?
O2 C2 C3 C4 179.9(2) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C2 C1 C6 C5 1.7(4) . . . . ?
O1 C1 C6 C5 177.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.75(4) 2.42(3) 2.815(2) 115(3) . yes
O2 H2 O2 0.75(4) 2.08(4) 2.7814(19) 158(3) 4_566 yes
O3 H3 O5 0.82(4) 1.73(4) 2.549(3) 178(4) 1_455 yes
O4 H4 O5 0.80(3) 1.79(3) 2.586(2) 169(4) 4_456 yes

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_khas17_1
_database_code_depnum_ccdc_archive 'CCDC 1852086'
_audit_update_record             
;
2018-06-27 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;

# start Validation Reply
_vrf_PLAT029_khas17_1            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.965 Note  
RESPONSE: Some reflections are affected by the beam-stop.
;
_vrf_PLAT334_khas17_1            
;
PROBLEM: Small Average Benzene  C-C Dist. C8     -C13           1.37 Ang.  
RESPONSE: The small average benzene ring distance is due to large thermal motion.
;
# end Validation Reply

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'1,1- phenylenedioxa-5-phenyl-3,7-bis(ethoxycarbonyl)-3,7-bis(trifluoromethyl)-1-phospha-2,6,8-trioxabicyclo[4.3.2(1,5)]octane'
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H21 F6 O9 P'
_chemical_formula_sum            'C24 H21 F6 O9 P'
_chemical_properties_physical    'hygroscopic, air-sensitive'
_exptl_crystal_recrystallization_method 
'crystallized from a pentane-dichloromethane solution'
_chemical_melting_point          407

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         598.38

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_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.
;

_cell_length_a                   10.7892(6)
_cell_length_b                   11.1562(6)
_cell_length_c                   11.7122(6)
_cell_angle_alpha                101.788(3)
_cell_angle_beta                 99.647(3)
_cell_angle_gamma                106.558(3)
_cell_volume                     1283.93(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7323
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      22.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.134
_exptl_absorpt_coefficient_mu    0.203
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6818
_exptl_absorpt_correction_T_max  0.7372
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38254
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.977
_diffrn_reflns_theta_max         25.283
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             4510
_reflns_number_gt                2940
_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       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'APEX2 v2014.11-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_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     
'w=1/[σ²(Fo²)+(0.0620P)²+0.2259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4510
_refine_ls_number_parameters     383
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.031
_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 0.34942(6) 0.73797(6) 0.63207(5) 0.0401(2) Uani 1 1 d . . . . .
F1 F 0.33825(18) 1.05970(14) 0.87616(16) 0.0752(5) Uani 1 1 d . . . . .
F2 F 0.1712(2) 1.02772(17) 0.73374(19) 0.0927(6) Uani 1 1 d . . . . .
F3 F 0.1423(2) 0.98224(17) 0.89902(19) 0.0942(6) Uani 1 1 d . . . . .
F4 F 0.47414(17) 0.52170(14) 0.66751(15) 0.0696(5) Uani 1 1 d . . . . .
F5 F 0.59473(18) 0.65453(16) 0.59077(15) 0.0763(5) Uani 1 1 d . . . . .
F6 F 0.66731(17) 0.64691(17) 0.77103(17) 0.0792(5) Uani 1 1 d . . . . .
O1 O 0.44731(17) 0.83283(15) 0.56580(14) 0.0512(5) Uani 1 1 d . . . . .
O2 O 0.30260(15) 0.85558(14) 0.68858(14) 0.0431(4) Uani 1 1 d . . . . .
O3 O 0.26822(16) 0.63600(15) 0.50453(13) 0.0448(4) Uani 1 1 d . . . . .
O6 O 0.45103(15) 0.70556(15) 0.84035(13) 0.0431(4) Uani 1 1 d . . . . .
O8 O 0.25853(14) 0.63142(14) 0.69219(12) 0.0377(4) Uani 1 1 d . . . . .
O14 O -0.0071(2) 0.7076(2) 0.7542(2) 0.0868(7) Uani 1 1 d . . . . .
O24 O 0.58174(19) 0.96076(18) 0.86589(17) 0.0649(5) Uani 1 1 d . . . . .
O25 O 0.70158(19) 0.89712(18) 0.74249(19) 0.0721(6) Uani 1 1 d . . . . .
C3 C 0.2166(2) 0.8408(2) 0.7703(2) 0.0457(6) Uani 1 1 d . . . . .
C4 C 0.2685(3) 0.7873(2) 0.8708(2) 0.0458(6) Uani 1 1 d . . . . .
H4A H 0.200567 0.762902 0.914425 0.055 Uiso 1 1 calc R U . . .
H4B H 0.346018 0.853695 0.926657 0.055 Uiso 1 1 calc R U . . .
C5 C 0.3063(2) 0.6680(2) 0.81822(19) 0.0376(6) Uani 1 1 d . . . . .
C7 C 0.4984(2) 0.7415(2) 0.7437(2) 0.0414(6) Uani 1 1 d . . . . .
C8 C 0.4154(3) 0.7846(2) 0.4425(2) 0.0455(6) Uani 1 1 d . . . . .
C9 C 0.4758(3) 0.8357(3) 0.3614(3) 0.0598(8) Uani 1 1 d . . . . .
H9 H 0.547618 0.912557 0.385205 0.072 Uiso 1 1 calc R U . . .
C10 C 0.4238(3) 0.7664(3) 0.2412(3) 0.0664(8) Uani 1 1 d . . . . .
H10 H 0.462218 0.797559 0.183092 0.080 Uiso 1 1 calc R U . . .
C11 C 0.3177(3) 0.6535(3) 0.2062(2) 0.0614(8) Uani 1 1 d . . . . .
H11 H 0.285430 0.610177 0.124993 0.074 Uiso 1 1 calc R U . . .
C12 C 0.2576(3) 0.6025(3) 0.2890(2) 0.0496(7) Uani 1 1 d . . . . .
H12 H 0.185535 0.525905 0.266007 0.060 Uiso 1 1 calc R U . . .
C13 C 0.3101(2) 0.6713(2) 0.4063(2) 0.0414(6) Uani 1 1 d . . . . .
C14 C 0.0725(3) 0.7577(3) 0.7033(3) 0.0617(8) Uani 1 1 d D . . . .
O15 O 0.04942(19) 0.75202(19) 0.5885(2) 0.0773(6) Uani 1 1 d D U . . .
C15 C -0.0992(8) 0.6862(13) 0.5363(11) 0.069(3) Uani 0.518(19) 1 d D U P A 1
H15A H -0.124012 0.593274 0.526353 0.083 Uiso 0.518(19) 1 calc R U P A 1
H15B H -0.149568 0.721083 0.587457 0.083 Uiso 0.518(19) 1 calc R U P A 1
C16 C -0.1221(17) 0.7160(18) 0.4182(10) 0.084(5) Uani 0.518(19) 1 d D U P A 1
H16A H -0.095645 0.808343 0.430326 0.126 Uiso 0.518(19) 1 calc R U P A 1
H16B H -0.214915 0.677660 0.378350 0.126 Uiso 0.518(19) 1 calc R U P A 1
H16C H -0.070518 0.681363 0.369638 0.126 Uiso 0.518(19) 1 calc R U P A 1
C15' C -0.0659(13) 0.6569(10) 0.4888(15) 0.081(4) Uani 0.482(19) 1 d D U P A 2
H15C H -0.034722 0.620406 0.421207 0.097 Uiso 0.482(19) 1 calc R U P A 2
H15D H -0.116525 0.586878 0.517076 0.097 Uiso 0.482(19) 1 calc R U P A 2
C16' C -0.1477(17) 0.7376(18) 0.4550(17) 0.089(5) Uani 0.482(19) 1 d D U P A 2
H16D H -0.168627 0.780591 0.525248 0.133 Uiso 0.482(19) 1 calc R U P A 2
H16E H -0.228679 0.682955 0.397291 0.133 Uiso 0.482(19) 1 calc R U P A 2
H16F H -0.098378 0.801153 0.420565 0.133 Uiso 0.482(19) 1 calc R U P A 2
C17 C 0.2180(3) 0.9793(3) 0.8197(3) 0.0627(8) Uani 1 1 d . . . . .
C18 C 0.2574(2) 0.5507(2) 0.86546(19) 0.0394(6) Uani 1 1 d . . . . .
C19 C 0.3387(3) 0.4807(2) 0.8967(2) 0.0517(7) Uani 1 1 d . . . . .
H19 H 0.426935 0.507276 0.891468 0.062 Uiso 1 1 calc R U . . .
C20 C 0.2897(3) 0.3717(3) 0.9356(3) 0.0629(8) Uani 1 1 d . . . . .
H20 H 0.345539 0.325780 0.956949 0.075 Uiso 1 1 calc R U . . .
C21 C 0.1599(3) 0.3305(3) 0.9432(3) 0.0656(8) Uani 1 1 d . . . . .
H21 H 0.127785 0.257410 0.970037 0.079 Uiso 1 1 calc R U . . .
C22 C 0.0774(3) 0.3979(3) 0.9108(3) 0.0619(8) Uani 1 1 d . . . . .
H22 H -0.011281 0.369761 0.914742 0.074 Uiso 1 1 calc R U . . .
C23 C 0.1259(3) 0.5078(2) 0.8722(2) 0.0517(7) Uani 1 1 d . . . . .
H23 H 0.069528 0.553152 0.850721 0.062 Uiso 1 1 calc R U . . .
C24 C 0.5996(2) 0.8810(3) 0.7923(2) 0.0478(6) Uani 1 1 d . . . . .
C25 C 0.8007(3) 1.0265(3) 0.7774(4) 0.0985(13) Uani 1 1 d D . . . .
H25A H 0.762252 1.090382 0.810460 0.118 Uiso 1 1 calc R U . . .
H25B H 0.875871 1.030713 0.838437 0.118 Uiso 1 1 calc R U . . .
C26 C 0.8447(4) 1.0538(4) 0.6732(4) 0.1234(16) Uani 1 1 d D . . . .
H26A H 0.886776 0.992930 0.643361 0.185 Uiso 1 1 calc R U . . .
H26B H 0.907098 1.140260 0.694660 0.185 Uiso 1 1 calc R U . . .
H26C H 0.769400 1.046368 0.612056 0.185 Uiso 1 1 calc R U . . .
C27 C 0.5601(3) 0.6414(3) 0.6923(3) 0.0549(7) 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 O2 1.5968(17) . ?
P1 O3 1.6100(16) . ?
P1 O8 1.6672(16) . ?
P1 O1 1.6766(17) . ?
P1 C7 1.880(2) . ?
F1 C17 1.316(3) . ?
F2 C17 1.330(3) . ?
F3 C17 1.337(3) . ?
F4 C27 1.332(3) . ?
F5 C27 1.328(3) . ?
F6 C27 1.330(3) . ?
O1 C8 1.380(3) . ?
O2 C3 1.442(3) . ?
O3 C13 1.393(3) . ?
O6 C7 1.403(3) . ?
O6 C5 1.458(3) . ?
O8 C5 1.411(3) . ?
O14 C14 1.200(3) . ?
O24 C24 1.188(3) . ?
O25 C24 1.315(3) . ?
O25 C25 1.458(3) . ?
C3 C4 1.521(3) . ?
C3 C17 1.530(4) . ?
C3 C14 1.538(4) . ?
C4 C5 1.542(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C18 1.516(3) . ?
C7 C27 1.529(4) . ?
C7 C24 1.549(3) . ?
C8 C9 1.367(3) . ?
C8 C13 1.367(3) . ?
C9 C10 1.392(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(3) . ?
C12 H12 0.9300 . ?
C14 O15 1.311(4) . ?
O15 C15' 1.514(8) . ?
O15 C15 1.516(8) . ?
C15 C16 1.485(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15' C16' 1.493(11) . ?
C15' H15C 0.9700 . ?
C15' H15D 0.9700 . ?
C16' H16D 0.9600 . ?
C16' H16E 0.9600 . ?
C16' H16F 0.9600 . ?
C18 C19 1.383(3) . ?
C18 C23 1.384(3) . ?
C19 C20 1.381(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C25 C26 1.438(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O3 121.68(9) . . ?
O2 P1 O8 95.66(8) . . ?
O3 P1 O8 85.65(8) . . ?
O2 P1 O1 90.41(9) . . ?
O3 P1 O1 91.49(8) . . ?
O8 P1 O1 173.92(9) . . ?
O2 P1 C7 107.72(9) . . ?
O3 P1 C7 130.49(10) . . ?
O8 P1 C7 86.53(9) . . ?
O1 P1 C7 91.27(10) . . ?
C8 O1 P1 112.66(14) . . ?
C3 O2 P1 120.22(14) . . ?
C13 O3 P1 114.12(14) . . ?
C7 O6 C5 112.50(16) . . ?
C5 O8 P1 110.36(13) . . ?
C24 O25 C25 117.2(2) . . ?
O2 C3 C4 112.04(19) . . ?
O2 C3 C17 103.07(19) . . ?
C4 C3 C17 111.0(2) . . ?
O2 C3 C14 111.4(2) . . ?
C4 C3 C14 111.4(2) . . ?
C17 C3 C14 107.6(2) . . ?
C3 C4 C5 109.99(19) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
O8 C5 O6 105.77(16) . . ?
O8 C5 C18 108.96(17) . . ?
O6 C5 C18 108.02(18) . . ?
O8 C5 C4 108.48(18) . . ?
O6 C5 C4 108.95(18) . . ?
C18 C5 C4 116.17(18) . . ?
O6 C7 C27 107.06(19) . . ?
O6 C7 C24 107.61(19) . . ?
C27 C7 C24 113.2(2) . . ?
O6 C7 P1 106.23(14) . . ?
C27 C7 P1 111.73(17) . . ?
C24 C7 P1 110.60(16) . . ?
C9 C8 C13 121.2(2) . . ?
C9 C8 O1 128.1(2) . . ?
C13 C8 O1 110.7(2) . . ?
C8 C9 C10 116.3(3) . . ?
C8 C9 H9 121.8 . . ?
C10 C9 H9 121.8 . . ?
C11 C10 C9 121.8(3) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 116.0(2) . . ?
C13 C12 H12 122.0 . . ?
C11 C12 H12 122.0 . . ?
C12 C13 C8 123.2(2) . . ?
C12 C13 O3 125.8(2) . . ?
C8 C13 O3 111.0(2) . . ?
O14 C14 O15 125.9(3) . . ?
O14 C14 C3 122.0(3) . . ?
O15 C14 C3 112.1(3) . . ?
C14 O15 C15' 127.7(8) . . ?
C14 O15 C15 107.2(5) . . ?
C16 C15 O15 103.7(9) . . ?
C16 C15 H15A 111.0 . . ?
O15 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
O15 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C16' C15' O15 103.6(10) . . ?
C16' C15' H15C 111.0 . . ?
O15 C15' H15C 111.0 . . ?
C16' C15' H15D 111.0 . . ?
O15 C15' H15D 111.0 . . ?
H15C C15' H15D 109.0 . . ?
C15' C16' H16D 109.5 . . ?
C15' C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
C15' C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
F1 C17 F2 107.3(2) . . ?
F1 C17 F3 106.7(3) . . ?
F2 C17 F3 107.3(2) . . ?
F1 C17 C3 112.5(2) . . ?
F2 C17 C3 112.2(2) . . ?
F3 C17 C3 110.4(2) . . ?
C19 C18 C23 118.5(2) . . ?
C19 C18 C5 121.9(2) . . ?
C23 C18 C5 119.5(2) . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 119.6(3) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 120.6(3) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
O24 C24 O25 126.4(2) . . ?
O24 C24 C7 121.3(2) . . ?
O25 C24 C7 112.3(2) . . ?
C26 C25 O25 108.9(3) . . ?
C26 C25 H25A 109.9 . . ?
O25 C25 H25A 109.9 . . ?
C26 C25 H25B 109.9 . . ?
O25 C25 H25B 109.9 . . ?
H25A C25 H25B 108.3 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
F5 C27 F6 108.2(2) . . ?
F5 C27 F4 106.4(2) . . ?
F6 C27 F4 106.8(2) . . ?
F5 C27 C7 113.5(2) . . ?
F6 C27 C7 111.2(2) . . ?
F4 C27 C7 110.6(2) . . ?

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
O2 P1 O1 C8 -121.28(17) . . . . ?
O3 P1 O1 C8 0.43(17) . . . . ?
C7 P1 O1 C8 130.99(17) . . . . ?
O3 P1 O2 C3 92.58(17) . . . . ?
O8 P1 O2 C3 4.21(17) . . . . ?
O1 P1 O2 C3 -175.42(16) . . . . ?
C7 P1 O2 C3 -83.95(17) . . . . ?
O2 P1 O3 C13 90.03(17) . . . . ?
O8 P1 O3 C13 -176.00(16) . . . . ?
O1 P1 O3 C13 -1.37(17) . . . . ?
C7 P1 O3 C13 -94.32(18) . . . . ?
O2 P1 O8 C5 -67.26(15) . . . . ?
O3 P1 O8 C5 171.30(15) . . . . ?
C7 P1 O8 C5 40.23(15) . . . . ?
P1 O2 C3 C4 50.5(2) . . . . ?
P1 O2 C3 C17 169.88(17) . . . . ?
P1 O2 C3 C14 -75.0(2) . . . . ?
O2 C3 C4 C5 -48.3(3) . . . . ?
C17 C3 C4 C5 -162.9(2) . . . . ?
C14 C3 C4 C5 77.2(3) . . . . ?
P1 O8 C5 O6 -44.34(19) . . . . ?
P1 O8 C5 C18 -160.24(15) . . . . ?
P1 O8 C5 C4 72.41(19) . . . . ?
C7 O6 C5 O8 22.7(2) . . . . ?
C7 O6 C5 C18 139.23(18) . . . . ?
C7 O6 C5 C4 -93.8(2) . . . . ?
C3 C4 C5 O8 -10.6(3) . . . . ?
C3 C4 C5 O6 104.1(2) . . . . ?
C3 C4 C5 C18 -133.7(2) . . . . ?
C5 O6 C7 C27 -114.7(2) . . . . ?
C5 O6 C7 C24 123.31(19) . . . . ?
C5 O6 C7 P1 4.8(2) . . . . ?
O2 P1 C7 O6 69.76(16) . . . . ?
O3 P1 C7 O6 -106.35(16) . . . . ?
O8 P1 C7 O6 -25.08(14) . . . . ?
O1 P1 C7 O6 160.60(14) . . . . ?
O2 P1 C7 C27 -173.83(16) . . . . ?
O3 P1 C7 C27 10.1(2) . . . . ?
O8 P1 C7 C27 91.34(18) . . . . ?
O1 P1 C7 C27 -82.99(18) . . . . ?
O2 P1 C7 C24 -46.73(19) . . . . ?
O3 P1 C7 C24 137.15(16) . . . . ?
O8 P1 C7 C24 -141.57(17) . . . . ?
O1 P1 C7 C24 44.11(17) . . . . ?
P1 O1 C8 C9 -178.8(2) . . . . ?
P1 O1 C8 C13 0.6(3) . . . . ?
C13 C8 C9 C10 0.2(4) . . . . ?
O1 C8 C9 C10 179.6(3) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C11 C12 C13 C8 0.4(4) . . . . ?
C11 C12 C13 O3 -177.8(2) . . . . ?
C9 C8 C13 C12 -0.5(4) . . . . ?
O1 C8 C13 C12 179.9(2) . . . . ?
C9 C8 C13 O3 177.9(2) . . . . ?
O1 C8 C13 O3 -1.6(3) . . . . ?
P1 O3 C13 C12 -179.6(2) . . . . ?
P1 O3 C13 C8 2.0(3) . . . . ?
O2 C3 C14 O14 161.7(2) . . . . ?
C4 C3 C14 O14 35.8(4) . . . . ?
C17 C3 C14 O14 -86.1(3) . . . . ?
O2 C3 C14 O15 -19.6(3) . . . . ?
C4 C3 C14 O15 -145.5(2) . . . . ?
C17 C3 C14 O15 92.7(3) . . . . ?
O14 C14 O15 C15' -17.3(9) . . . . ?
C3 C14 O15 C15' 164.0(7) . . . . ?
O14 C14 O15 C15 7.3(7) . . . . ?
C3 C14 O15 C15 -171.4(7) . . . . ?
C14 O15 C15 C16 164.8(13) . . . . ?
C14 O15 C15' C16' 108.9(14) . . . . ?
O2 C3 C17 F1 -60.4(3) . . . . ?
C4 C3 C17 F1 59.7(3) . . . . ?
C14 C3 C17 F1 -178.2(3) . . . . ?
O2 C3 C17 F2 60.8(3) . . . . ?
C4 C3 C17 F2 -179.1(2) . . . . ?
C14 C3 C17 F2 -57.0(3) . . . . ?
O2 C3 C17 F3 -179.5(2) . . . . ?
C4 C3 C17 F3 -59.4(3) . . . . ?
C14 C3 C17 F3 62.7(3) . . . . ?
O8 C5 C18 C19 101.3(2) . . . . ?
O6 C5 C18 C19 -13.1(3) . . . . ?
C4 C5 C18 C19 -135.8(2) . . . . ?
O8 C5 C18 C23 -75.4(3) . . . . ?
O6 C5 C18 C23 170.2(2) . . . . ?
C4 C5 C18 C23 47.4(3) . . . . ?
C23 C18 C19 C20 -1.0(4) . . . . ?
C5 C18 C19 C20 -177.8(2) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C20 C21 C22 C23 -0.8(4) . . . . ?
C19 C18 C23 C22 0.7(4) . . . . ?
C5 C18 C23 C22 177.5(2) . . . . ?
C21 C22 C23 C18 0.2(4) . . . . ?
C25 O25 C24 O24 -2.2(4) . . . . ?
C25 O25 C24 C7 177.3(3) . . . . ?
O6 C7 C24 O24 -38.5(3) . . . . ?
C27 C7 C24 O24 -156.6(3) . . . . ?
P1 C7 C24 O24 77.2(3) . . . . ?
O6 C7 C24 O25 141.9(2) . . . . ?
C27 C7 C24 O25 23.8(3) . . . . ?
P1 C7 C24 O25 -102.4(2) . . . . ?
C24 O25 C25 C26 -141.2(3) . . . . ?
O6 C7 C27 F5 172.3(2) . . . . ?
C24 C7 C27 F5 -69.3(3) . . . . ?
P1 C7 C27 F5 56.3(3) . . . . ?
O6 C7 C27 F6 -65.6(3) . . . . ?
C24 C7 C27 F6 52.9(3) . . . . ?
P1 C7 C27 F6 178.52(17) . . . . ?
O6 C7 C27 F4 52.9(3) . . . . ?
C24 C7 C27 F4 171.3(2) . . . . ?
P1 C7 C27 F4 -63.0(3) . . . . ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_khas61_sq
_database_code_depnum_ccdc_archive 'CCDC 1852087'
_audit_update_record             
;
2018-06-27 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
1,1-phenylenedioxa-5-phenyl-3,7-bis(trichloromethyl)-1-phospha-2,6,8-trioxabicyclo[4.3.2(1,5)]octane
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H13 Cl6 O5 P'
_chemical_formula_sum            'C18 H13 Cl6 O5 P'
# SQUEEZED solvent info is not included in the formula and related items 
# such as molecular weight and calculated density.
_chemical_properties_physical    'hygroscopic, air-sensitive'
_exptl_crystal_recrystallization_method 
'crystallized from a pentane-chloroform solution'
_chemical_melting_point          414

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         552.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

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

_cell_length_a                   27.972(6)
_cell_length_b                   27.972(6)
_cell_length_c                   11.844(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9268(5)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25.79
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_F_000             4448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.599
_exptl_crystal_size_mid          0.494
_exptl_crystal_size_min          0.461
_exptl_absorpt_coefficient_mu    0.838
_shelx_estimated_absorpt_T_min   0.634
_shelx_estimated_absorpt_T_max   0.699
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9103
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34206
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.867
_diffrn_reflns_theta_max         25.699
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4413
_reflns_number_gt                3637
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'APEX2 v2014.11-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_refine_special_details          
;
The unit cell contains highly disordered solvent molecules (pentane),
which were treated as a diffuse contribution to the overall scattering
without specific atom positions by PLATON/SQUEEZE-290617 (Spek, 2015).

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     
'w=1/[σ²(Fo²)+(0.0398P)²+17.5400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4413
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.30566(2) 0.72767(2) 0.44435(5) 0.02980(15) Uani 1 1 d . . . . .
O1 O 0.32212(6) 0.67842(6) 0.51807(15) 0.0385(4) Uani 1 1 d . . . . .
O2 O 0.33128(6) 0.70594(6) 0.33569(14) 0.0351(4) Uani 1 1 d . . . . .
O3 O 0.24962(6) 0.71700(6) 0.46782(14) 0.0350(4) Uani 1 1 d . . . . .
O6 O 0.36079(6) 0.80217(6) 0.44548(14) 0.0387(4) Uani 1 1 d . . . . .
O8 O 0.28718(5) 0.77795(5) 0.38055(13) 0.0299(3) Uani 1 1 d . . . . .
Cl1 Cl 0.42307(3) 0.69535(3) 0.20483(8) 0.0678(2) Uani 1 1 d . . . . .
Cl2 Cl 0.33963(3) 0.64288(2) 0.14042(7) 0.0597(2) Uani 1 1 d . . . . .
Cl3 Cl 0.36589(3) 0.72683(3) 0.01698(6) 0.0606(2) Uani 1 1 d . . . . .
Cl4 Cl 0.27911(3) 0.81753(4) 0.62555(8) 0.0770(3) Uani 1 1 d . . . . .
Cl5 Cl 0.32802(5) 0.74049(4) 0.73546(7) 0.0961(4) Uani 1 1 d . . . . .
Cl6 Cl 0.37755(3) 0.82764(3) 0.68186(7) 0.0658(2) Uani 1 1 d . . . . .
C3 C 0.33310(9) 0.73147(8) 0.2297(2) 0.0338(5) Uani 1 1 d . . . . .
H3 H 0.300819 0.732975 0.197754 0.041 Uiso 1 1 calc R U . . .
C4 C 0.35156(9) 0.78225(9) 0.2471(2) 0.0380(6) Uani 1 1 d . . . . .
H4A H 0.344652 0.801305 0.180671 0.046 Uiso 1 1 calc R U . . .
H4B H 0.385955 0.781570 0.257446 0.046 Uiso 1 1 calc R U . . .
C5 C 0.32785(8) 0.80516(8) 0.3511(2) 0.0317(5) Uani 1 1 d . . . . .
C7 C 0.34943(8) 0.76545(9) 0.5208(2) 0.0336(5) Uani 1 1 d . . . . .
H7 H 0.378346 0.746374 0.533184 0.040 Uiso 1 1 calc R U . . .
C8 C 0.28377(9) 0.65136(9) 0.5497(2) 0.0360(5) Uani 1 1 d . . . . .
C9 C 0.28440(11) 0.60761(10) 0.6015(2) 0.0467(7) Uani 1 1 d . . . . .
H9 H 0.312873 0.591950 0.618125 0.056 Uiso 1 1 calc R U . . .
C10 C 0.23998(11) 0.58775(10) 0.6280(3) 0.0524(7) Uani 1 1 d . . . . .
H10 H 0.238853 0.558081 0.663288 0.063 Uiso 1 1 calc R U . . .
C11 C 0.19792(11) 0.61084(10) 0.6033(3) 0.0510(7) Uani 1 1 d . . . . .
H11 H 0.169023 0.596638 0.622875 0.061 Uiso 1 1 calc R U . . .
C12 C 0.19773(10) 0.65483(9) 0.5499(2) 0.0431(6) Uani 1 1 d . . . . .
H12 H 0.169420 0.670637 0.532631 0.052 Uiso 1 1 calc R U . . .
C13 C 0.24143(9) 0.67382(8) 0.5240(2) 0.0348(5) Uani 1 1 d . . . . .
C14 C 0.36441(10) 0.70060(9) 0.1533(2) 0.0401(6) Uani 1 1 d . . . . .
C15 C 0.31512(9) 0.85702(8) 0.3320(2) 0.0333(5) Uani 1 1 d . . . . .
C16 C 0.28022(10) 0.86815(10) 0.2543(3) 0.0495(7) Uani 1 1 d . . . . .
H16 H 0.262853 0.843749 0.220268 0.059 Uiso 1 1 calc R U . . .
C17 C 0.27072(12) 0.91511(11) 0.2264(3) 0.0636(9) Uani 1 1 d . . . . .
H17 H 0.247480 0.922154 0.172824 0.076 Uiso 1 1 calc R U . . .
C18 C 0.29550(13) 0.95135(10) 0.2777(3) 0.0615(9) Uani 1 1 d . . . . .
H18 H 0.288953 0.983022 0.259556 0.074 Uiso 1 1 calc R U . . .
C19 C 0.32981(13) 0.94072(10) 0.3555(3) 0.0591(8) Uani 1 1 d . . . . .
H19 H 0.346492 0.965344 0.390530 0.071 Uiso 1 1 calc R U . . .
C20 C 0.34016(11) 0.89360(10) 0.3830(2) 0.0473(7) Uani 1 1 d . . . . .
H20 H 0.363873 0.886733 0.435530 0.057 Uiso 1 1 calc R U . . .
C21 C 0.33390(10) 0.78623(10) 0.6352(2) 0.0460(6) 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 O2 1.5934(17) . ?
P1 O3 1.6198(17) . ?
P1 O8 1.6783(16) . ?
P1 O1 1.6947(17) . ?
P1 C7 1.854(2) . ?
O1 C8 1.365(3) . ?
O2 C3 1.445(3) . ?
O3 C13 1.398(3) . ?
O6 C7 1.397(3) . ?
O6 C5 1.451(3) . ?
O8 C5 1.413(3) . ?
Cl1 C14 1.757(3) . ?
Cl2 C14 1.764(3) . ?
Cl3 C14 1.775(3) . ?
Cl4 C21 1.769(3) . ?
Cl5 C21 1.754(3) . ?
Cl6 C21 1.772(3) . ?
C3 C4 1.525(3) . ?
C3 C14 1.527(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.539(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C15 1.511(3) . ?
C7 C21 1.536(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.369(4) . ?
C8 C13 1.375(4) . ?
C9 C10 1.397(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.368(4) . ?
C12 H12 0.9300 . ?
C15 C16 1.377(4) . ?
C15 C20 1.379(4) . ?
C16 C17 1.380(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.388(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O3 120.24(9) . . ?
O2 P1 O8 95.42(8) . . ?
O3 P1 O8 86.19(8) . . ?
O2 P1 O1 89.08(9) . . ?
O3 P1 O1 91.42(8) . . ?
O8 P1 O1 175.50(9) . . ?
O2 P1 C7 108.37(10) . . ?
O3 P1 C7 131.32(10) . . ?
O8 P1 C7 86.88(9) . . ?
O1 P1 C7 91.84(10) . . ?
C8 O1 P1 112.23(15) . . ?
C3 O2 P1 121.95(14) . . ?
C13 O3 P1 113.53(15) . . ?
C7 O6 C5 112.96(17) . . ?
C5 O8 P1 108.35(13) . . ?
O2 C3 C4 110.77(19) . . ?
O2 C3 C14 104.80(19) . . ?
C4 C3 C14 114.4(2) . . ?
O2 C3 H3 108.9 . . ?
C4 C3 H3 108.9 . . ?
C14 C3 H3 108.9 . . ?
C3 C4 C5 110.5(2) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
O8 C5 O6 106.86(18) . . ?
O8 C5 C15 111.38(18) . . ?
O6 C5 C15 108.71(19) . . ?
O8 C5 C4 108.68(19) . . ?
O6 C5 C4 108.60(19) . . ?
C15 C5 C4 112.4(2) . . ?
O6 C7 C21 110.4(2) . . ?
O6 C7 P1 104.90(15) . . ?
C21 C7 P1 117.37(17) . . ?
O6 C7 H7 107.9 . . ?
C21 C7 H7 107.9 . . ?
P1 C7 H7 107.9 . . ?
O1 C8 C9 127.5(2) . . ?
O1 C8 C13 111.3(2) . . ?
C9 C8 C13 121.3(2) . . ?
C8 C9 C10 116.4(3) . . ?
C8 C9 H9 121.8 . . ?
C10 C9 H9 121.8 . . ?
C11 C10 C9 121.8(3) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 121.2(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 116.4(3) . . ?
C13 C12 H12 121.8 . . ?
C11 C12 H12 121.8 . . ?
C12 C13 C8 122.9(2) . . ?
C12 C13 O3 126.1(2) . . ?
C8 C13 O3 111.1(2) . . ?
C3 C14 Cl1 112.17(18) . . ?
C3 C14 Cl2 110.11(18) . . ?
Cl1 C14 Cl2 108.71(14) . . ?
C3 C14 Cl3 108.59(17) . . ?
Cl1 C14 Cl3 109.19(15) . . ?
Cl2 C14 Cl3 107.98(14) . . ?
C16 C15 C20 119.0(2) . . ?
C16 C15 C5 119.0(2) . . ?
C20 C15 C5 121.8(2) . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.8(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 119.7(3) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C7 C21 Cl5 110.33(19) . . ?
C7 C21 Cl4 112.06(18) . . ?
Cl5 C21 Cl4 108.88(16) . . ?
C7 C21 Cl6 109.14(19) . . ?
Cl5 C21 Cl6 109.27(15) . . ?
Cl4 C21 Cl6 107.07(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
O2 P1 O1 C8 -113.54(17) . . . . ?
O3 P1 O1 C8 6.68(17) . . . . ?
C7 P1 O1 C8 138.11(17) . . . . ?
O3 P1 O2 C3 90.61(18) . . . . ?
O8 P1 O2 C3 1.87(18) . . . . ?
O1 P1 O2 C3 -178.27(18) . . . . ?
C7 P1 O2 C3 -86.64(19) . . . . ?
O2 P1 O3 C13 84.73(18) . . . . ?
O8 P1 O3 C13 178.78(16) . . . . ?
O1 P1 O3 C13 -5.04(17) . . . . ?
C7 P1 O3 C13 -98.75(19) . . . . ?
O2 P1 O8 C5 -65.90(15) . . . . ?
O3 P1 O8 C5 174.06(15) . . . . ?
C7 P1 O8 C5 42.27(15) . . . . ?
P1 O2 C3 C4 51.0(2) . . . . ?
P1 O2 C3 C14 174.79(16) . . . . ?
O2 C3 C4 C5 -44.1(3) . . . . ?
C14 C3 C4 C5 -162.2(2) . . . . ?
P1 O8 C5 O6 -41.33(19) . . . . ?
P1 O8 C5 C15 -159.92(16) . . . . ?
P1 O8 C5 C4 75.69(19) . . . . ?
C7 O6 C5 O8 15.3(2) . . . . ?
C7 O6 C5 C15 135.6(2) . . . . ?
C7 O6 C5 C4 -101.8(2) . . . . ?
C3 C4 C5 O8 -15.9(3) . . . . ?
C3 C4 C5 O6 100.0(2) . . . . ?
C3 C4 C5 C15 -139.7(2) . . . . ?
C5 O6 C7 C21 -113.3(2) . . . . ?
C5 O6 C7 P1 14.0(2) . . . . ?
O2 P1 C7 O6 62.82(17) . . . . ?
O3 P1 C7 O6 -114.01(16) . . . . ?
O8 P1 C7 O6 -31.85(15) . . . . ?
O1 P1 C7 O6 152.47(16) . . . . ?
O2 P1 C7 C21 -174.18(18) . . . . ?
O3 P1 C7 C21 9.0(3) . . . . ?
O8 P1 C7 C21 91.14(19) . . . . ?
O1 P1 C7 C21 -84.5(2) . . . . ?
P1 O1 C8 C9 174.1(2) . . . . ?
P1 O1 C8 C13 -6.5(3) . . . . ?
O1 C8 C9 C10 178.3(2) . . . . ?
C13 C8 C9 C10 -1.0(4) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C8 -0.7(4) . . . . ?
C11 C12 C13 O3 178.3(2) . . . . ?
O1 C8 C13 C12 -178.1(2) . . . . ?
C9 C8 C13 C12 1.4(4) . . . . ?
O1 C8 C13 O3 2.8(3) . . . . ?
C9 C8 C13 O3 -177.7(2) . . . . ?
P1 O3 C13 C12 -176.8(2) . . . . ?
P1 O3 C13 C8 2.3(3) . . . . ?
O2 C3 C14 Cl1 -63.0(2) . . . . ?
C4 C3 C14 Cl1 58.5(3) . . . . ?
O2 C3 C14 Cl2 58.2(2) . . . . ?
C4 C3 C14 Cl2 179.68(18) . . . . ?
O2 C3 C14 Cl3 176.22(16) . . . . ?
C4 C3 C14 Cl3 -62.3(2) . . . . ?
O8 C5 C15 C16 -55.6(3) . . . . ?
O6 C5 C15 C16 -173.0(2) . . . . ?
C4 C5 C15 C16 66.7(3) . . . . ?
O8 C5 C15 C20 130.0(2) . . . . ?
O6 C5 C15 C20 12.5(3) . . . . ?
C4 C5 C15 C20 -107.8(3) . . . . ?
C20 C15 C16 C17 0.9(4) . . . . ?
C5 C15 C16 C17 -173.7(3) . . . . ?
C15 C16 C17 C18 -1.2(5) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C17 C18 C19 C20 0.4(5) . . . . ?
C16 C15 C20 C19 0.1(4) . . . . ?
C5 C15 C20 C19 174.5(3) . . . . ?
C18 C19 C20 C15 -0.7(5) . . . . ?
O6 C7 C21 Cl5 -171.48(17) . . . . ?
P1 C7 C21 Cl5 68.4(2) . . . . ?
O6 C7 C21 Cl4 67.0(2) . . . . ?
P1 C7 C21 Cl4 -53.1(2) . . . . ?
O6 C7 C21 Cl6 -51.4(2) . . . . ?
P1 C7 C21 Cl6 -171.52(14) . . . . ?

_refine_diff_density_max         0.758
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.051



