# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_k60_fin2
_database_code_depnum_ccdc_archive 'CCDC 1474601'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H15 O5 P'
_chemical_formula_sum            'C6 H15 O5 P'
_chemical_formula_weight         198.15

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'

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

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

_cell_length_a                   6.390(15)
_cell_length_b                   10.62(3)
_cell_length_c                   14.67(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     995(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1077
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      21.18

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.262
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4801
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5025
_diffrn_reflns_av_unetI/netI     0.0861
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.368
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1949
_reflns_number_gt                1316
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1641P)²+0.9564P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 382 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1949
_refine_ls_number_parameters     124
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1841
_refine_ls_wR_factor_gt          0.1437
_refine_ls_goodness_of_fit_ref   0.698
_refine_ls_restrained_S_all      0.697
_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 0.8126(3) 0.47564(14) 0.39616(11) 0.0372(5) Uani 1 1 d . . . . .
O1S O 0.2827(8) 0.3588(6) 0.5010(4) 0.0510(12) Uani 1 1 d . . . . .
O1 O 0.7966(9) 0.6186(4) 0.4220(3) 0.0552(13) Uani 1 1 d . . . . .
O2 O 1.0442(8) 0.4418(5) 0.3840(4) 0.0596(14) Uani 1 1 d D . . . .
H2 H 1.119(12) 0.419(9) 0.430(4) 0.089 Uiso 1 1 d D U . . .
O3 O 0.7129(7) 0.4826(4) 0.2983(3) 0.0430(11) Uani 1 1 d . . . . .
O4 O 0.6983(7) 0.3880(4) 0.4564(3) 0.0512(12) Uani 1 1 d . . . . .
C9 C 0.4554(13) 0.7013(9) 0.3811(6) 0.077(3) Uani 1 1 d . . . . .
H91 H 0.3934 0.6189 0.3806 0.115 Uiso 1 1 calc R U . . .
H92 H 0.3818 0.7550 0.3394 0.115 Uiso 1 1 calc R U . . .
H93 H 0.4472 0.7358 0.4415 0.115 Uiso 1 1 calc R U . . .
C7 C 0.6810(13) 0.6919(5) 0.3528(4) 0.0449(15) Uani 1 1 d . . . . .
C8 C 0.7183(10) 0.6146(5) 0.2641(4) 0.0387(14) Uani 1 1 d . . . . .
C10 C 0.7867(17) 0.8214(6) 0.3487(6) 0.082(3) Uani 1 1 d . . . . .
H103 H 0.7542 0.8678 0.4031 0.124 Uiso 1 1 calc R U . . .
H101 H 0.7367 0.8667 0.2965 0.124 Uiso 1 1 calc R U . . .
H102 H 0.9355 0.8107 0.3441 0.124 Uiso 1 1 calc R U . . .
C12 C 0.9281(13) 0.6330(8) 0.2184(5) 0.065(2) Uani 1 1 d . . . . .
H122 H 1.0371 0.6282 0.2633 0.097 Uiso 1 1 calc R U . . .
H123 H 0.9316 0.7140 0.1894 0.097 Uiso 1 1 calc R U . . .
H121 H 0.9486 0.5684 0.1735 0.097 Uiso 1 1 calc R U . . .
C11 C 0.5447(14) 0.6259(8) 0.1948(5) 0.066(2) Uani 1 1 d . . . . .
H112 H 0.5807 0.5787 0.1412 0.100 Uiso 1 1 calc R U . . .
H113 H 0.5257 0.7128 0.1789 0.100 Uiso 1 1 calc R U . . .
H111 H 0.4173 0.5933 0.2203 0.100 Uiso 1 1 calc R U . . .
H1S H 0.259(14) 0.294(9) 0.511(6) 0.07(3) Uiso 1 1 d . . . . .
H2S H 0.406(15) 0.378(8) 0.490(5) 0.07(3) 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
P1 O4 1.476(5) . ?
P1 O2 1.534(6) . ?
P1 O1 1.569(6) . ?
P1 O3 1.572(5) . ?
O1S H1S 0.72(9) . ?
O1S H2S 0.83(10) . ?
O1 C7 1.478(8) . ?
O2 H2 0.87(3) . ?
O3 C8 1.489(7) . ?
C9 C7 1.503(11) . ?
C9 H91 0.9600 . ?
C9 H92 0.9600 . ?
C9 H93 0.9600 . ?
C7 C10 1.534(10) . ?
C7 C8 1.557(9) . ?
C8 C11 1.509(10) . ?
C8 C12 1.511(10) . ?
C10 H103 0.9600 . ?
C10 H101 0.9600 . ?
C10 H102 0.9600 . ?
C12 H122 0.9600 . ?
C12 H123 0.9600 . ?
C12 H121 0.9600 . ?
C11 H112 0.9600 . ?
C11 H113 0.9600 . ?
C11 H111 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 P1 O2 113.5(3) . . ?
O4 P1 O1 115.7(3) . . ?
O2 P1 O1 108.6(3) . . ?
O4 P1 O3 112.0(3) . . ?
O2 P1 O3 107.2(3) . . ?
O1 P1 O3 98.6(2) . . ?
H1S O1S H2S 119(9) . . ?
C7 O1 P1 112.1(4) . . ?
P1 O2 H2 120(6) . . ?
C8 O3 P1 110.0(3) . . ?
C7 C9 H91 109.5 . . ?
C7 C9 H92 109.5 . . ?
H91 C9 H92 109.5 . . ?
C7 C9 H93 109.5 . . ?
H91 C9 H93 109.5 . . ?
H92 C9 H93 109.5 . . ?
O1 C7 C9 108.9(6) . . ?
O1 C7 C10 106.1(6) . . ?
C9 C7 C10 112.0(7) . . ?
O1 C7 C8 102.7(5) . . ?
C9 C7 C8 114.4(6) . . ?
C10 C7 C8 111.9(6) . . ?
O3 C8 C11 106.6(5) . . ?
O3 C8 C12 107.0(5) . . ?
C11 C8 C12 110.1(6) . . ?
O3 C8 C7 102.2(4) . . ?
C11 C8 C7 114.1(6) . . ?
C12 C8 C7 116.0(6) . . ?
C7 C10 H103 109.5 . . ?
C7 C10 H101 109.5 . . ?
H103 C10 H101 109.5 . . ?
C7 C10 H102 109.5 . . ?
H103 C10 H102 109.5 . . ?
H101 C10 H102 109.5 . . ?
C8 C12 H122 109.5 . . ?
C8 C12 H123 109.5 . . ?
H122 C12 H123 109.5 . . ?
C8 C12 H121 109.5 . . ?
H122 C12 H121 109.5 . . ?
H123 C12 H121 109.5 . . ?
C8 C11 H112 109.5 . . ?
C8 C11 H113 109.5 . . ?
H112 C11 H113 109.5 . . ?
C8 C11 H111 109.5 . . ?
H112 C11 H111 109.5 . . ?
H113 C11 H111 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 P1 O1 C7 -113.5(5) . . . . ?
O2 P1 O1 C7 117.6(5) . . . . ?
O3 P1 O1 C7 6.1(5) . . . . ?
O4 P1 O3 C8 141.1(4) . . . . ?
O2 P1 O3 C8 -93.7(4) . . . . ?
O1 P1 O3 C8 18.8(4) . . . . ?
P1 O1 C7 C9 94.7(6) . . . . ?
P1 O1 C7 C10 -144.6(6) . . . . ?
P1 O1 C7 C8 -27.0(6) . . . . ?
P1 O3 C8 C11 -155.4(5) . . . . ?
P1 O3 C8 C12 86.9(5) . . . . ?
P1 O3 C8 C7 -35.4(6) . . . . ?
O1 C7 C8 O3 36.9(6) . . . . ?
C9 C7 C8 O3 -80.9(6) . . . . ?
C10 C7 C8 O3 150.4(6) . . . . ?
O1 C7 C8 C11 151.5(6) . . . . ?
C9 C7 C8 C11 33.6(8) . . . . ?
C10 C7 C8 C11 -95.0(8) . . . . ?
O1 C7 C8 C12 -79.0(6) . . . . ?
C9 C7 C8 C12 163.1(6) . . . . ?
C10 C7 C8 C12 34.5(8) . . . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1474602'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H25 F6 O6 P'
_chemical_formula_sum            'C23 H25 F6 O6 P'
_chemical_formula_weight         542.40

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

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

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

_cell_length_a                   10.788(13)
_cell_length_b                   10.889(13)
_cell_length_c                   12.329(15)
_cell_angle_alpha                70.63(2)
_cell_angle_beta                 71.74(2)
_cell_angle_gamma                67.883(19)
_cell_volume                     1236(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1507
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      19.64

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.193
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6196
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            4706
_diffrn_reflns_av_unetI/netI     0.1398
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.793
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             4706
_reflns_number_gt                2147
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4706
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1946
_refine_ls_R_factor_gt           0.0880
_refine_ls_wR_factor_ref         0.3522
_refine_ls_wR_factor_gt          0.2734
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.6676(2) 0.7929(2) 0.15391(18) 0.0398(6) Uani 1 1 d . . . . .
F1 F 0.3438(5) 0.8417(5) 0.3861(5) 0.0646(14) Uani 1 1 d . . . . .
O2 O 0.5760(5) 0.8934(5) 0.2363(4) 0.0374(12) Uani 1 1 d . . . . .
F2 F 0.3426(5) 0.8959(5) 0.2003(5) 0.0608(14) Uani 1 1 d . . . . .
O6 O 0.2100(6) 1.1642(6) 0.1922(6) 0.0470(15) Uani 1 1 d . . . . .
O7 O 0.4416(5) 1.0464(6) 0.3977(5) 0.0447(13) Uani 1 1 d . . . . .
F5 F 0.1562(5) 1.2499(5) 0.4085(5) 0.0632(14) Uani 1 1 d . . . . .
F4 F 0.1721(5) 1.0406(6) 0.4970(4) 0.0733(16) Uani 1 1 d . . . . .
F6 F 0.0303(4) 1.1559(5) 0.3824(5) 0.0645(14) Uani 1 1 d . . . . .
O4 O 0.6440(6) 0.8467(6) 0.0343(5) 0.0598(16) Uani 1 1 d . . . . .
O3 O 0.8233(5) 0.7517(5) 0.1590(5) 0.0459(14) Uani 1 1 d . . . . .
O1 O 0.6357(5) 0.6553(5) 0.2306(5) 0.0501(14) Uani 1 1 d . . . . .
F3 F 0.1529(5) 0.9189(5) 0.3285(6) 0.0759(17) Uani 1 1 d . . . . .
C13 C 0.6600(7) 1.0866(7) 0.1590(7) 0.0378(17) Uani 1 1 d . . . . .
C20 C 0.3779(8) 1.3429(7) 0.1425(7) 0.0437(19) Uani 1 1 d . . . . .
H20 H 0.3710 1.3075 0.0864 0.052 Uiso 1 1 calc R U . . .
C3 C 0.5345(7) 1.0430(7) 0.1880(7) 0.0381(17) Uani 1 1 d . . . . .
H3 H 0.5026 1.0645 0.1157 0.046 Uiso 1 1 calc R U . . .
C19 C 0.3971(7) 1.2590(7) 0.2513(6) 0.0384(17) Uani 1 1 d . . . . .
C4 C 0.4120(7) 1.1054(7) 0.2835(6) 0.0368(17) Uani 1 1 d . . . . .
C5 C 0.2681(7) 1.0841(7) 0.2880(6) 0.0362(17) Uani 1 1 d . . . . .
C26 C 0.1555(8) 1.1332(9) 0.3964(7) 0.052(2) Uani 1 1 d . . . . .
C21 C 0.3690(8) 1.4786(9) 0.1161(9) 0.056(2) Uani 1 1 d . . . . .
H21 H 0.3540 1.5341 0.0428 0.067 Uiso 1 1 calc R U . . .
C15 C 0.8539(8) 1.0972(10) 0.2100(9) 0.062(3) Uani 1 1 d . . . . .
H15 H 0.8991 1.0867 0.2671 0.074 Uiso 1 1 calc R U . . .
C25 C 0.2794(8) 0.9321(9) 0.3023(9) 0.053(2) Uani 1 1 d . . . . .
C14 C 0.7307(8) 1.0707(9) 0.2415(8) 0.053(2) Uani 1 1 d . . . . .
H14 H 0.6936 1.0411 0.3209 0.063 Uiso 1 1 calc R U . . .
C24 C 0.4103(9) 1.3142(9) 0.3335(8) 0.052(2) Uani 1 1 d . . . . .
H24 H 0.4246 1.2591 0.4072 0.063 Uiso 1 1 calc R U . . .
C18 C 0.7173(9) 1.1302(8) 0.0420(8) 0.052(2) Uani 1 1 d . . . . .
H18 H 0.6713 1.1432 -0.0152 0.062 Uiso 1 1 calc R U . . .
C12 C 0.8297(13) 0.6595(12) 0.3659(10) 0.083(3) Uani 1 1 d . . . . .
H122 H 0.8731 0.7265 0.3548 0.125 Uiso 1 1 calc R U . . .
H121 H 0.8640 0.5798 0.4245 0.125 Uiso 1 1 calc R U . . .
H123 H 0.7325 0.6967 0.3915 0.125 Uiso 1 1 calc R U . . .
C7 C 0.7673(8) 0.5440(8) 0.2478(8) 0.053(2) Uani 1 1 d . . . . .
C16 C 0.9084(10) 1.1393(9) 0.0937(11) 0.067(3) Uani 1 1 d . . . . .
H16 H 0.9916 1.1574 0.0722 0.080 Uiso 1 1 calc R U . . .
C22 C 0.3818(9) 1.5348(9) 0.1970(9) 0.061(3) Uani 1 1 d . . . . .
H22 H 0.3766 1.6264 0.1782 0.073 Uiso 1 1 calc R U . . .
C23 C 0.4022(11) 1.4516(11) 0.3049(10) 0.070(3) Uani 1 1 d . . . . .
H23 H 0.4107 1.4873 0.3601 0.084 Uiso 1 1 calc R U . . .
C9 C 0.7315(11) 0.4427(11) 0.3634(11) 0.088(4) Uani 1 1 d . . . . .
H91 H 0.6908 0.4890 0.4260 0.132 Uiso 1 1 calc R U . . .
H93 H 0.8133 0.3707 0.3802 0.132 Uiso 1 1 calc R U . . .
H92 H 0.6678 0.4047 0.3568 0.132 Uiso 1 1 calc R U . . .
C11 C 1.0131(9) 0.5538(11) 0.2080(12) 0.090(4) Uani 1 1 d . . . . .
H113 H 1.0313 0.5446 0.1293 0.135 Uiso 1 1 calc R U . . .
H112 H 1.0411 0.4652 0.2596 0.135 Uiso 1 1 calc R U . . .
H111 H 1.0632 0.6096 0.2095 0.135 Uiso 1 1 calc R U . . .
C8 C 0.8612(8) 0.6202(8) 0.2486(8) 0.052(2) Uani 1 1 d . . . . .
C17 C 0.8454(10) 1.1557(10) 0.0076(9) 0.067(3) Uani 1 1 d . . . . .
H17 H 0.8852 1.1828 -0.0715 0.080 Uiso 1 1 calc R U . . .
C10 C 0.8151(14) 0.4752(11) 0.1468(12) 0.098(4) Uani 1 1 d . . . . .
H101 H 0.7440 0.4438 0.1448 0.148 Uiso 1 1 calc R U . . .
H102 H 0.8958 0.3990 0.1579 0.148 Uiso 1 1 calc R U . . .
H103 H 0.8356 0.5395 0.0739 0.148 Uiso 1 1 calc R U . . .
H6 H 0.229(6) 1.181(6) 0.134(5) 0.002(18) Uiso 1 1 d . . . . .
H7 H 0.477(8) 0.959(8) 0.402(6) 0.04(2) 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
P1 O4 1.461(6) . ?
P1 O2 1.581(5) . ?
P1 O1 1.582(6) . ?
P1 O3 1.584(5) . ?
F1 C25 1.334(9) . ?
O2 C3 1.478(8) . ?
F2 C25 1.338(11) . ?
O6 C5 1.385(9) . ?
O6 H6 0.67(6) . ?
O7 C4 1.422(8) . ?
O7 H7 0.87(8) . ?
F5 C26 1.330(10) . ?
F4 C26 1.326(9) . ?
F6 C26 1.335(9) . ?
O3 C8 1.493(9) . ?
O1 C7 1.500(9) . ?
F3 C25 1.353(9) . ?
C13 C18 1.377(11) . ?
C13 C14 1.384(11) . ?
C13 C3 1.502(10) . ?
C20 C21 1.376(11) . ?
C20 C19 1.376(10) . ?
C20 H20 0.9300 . ?
C3 C4 1.572(11) . ?
C3 H3 0.9800 . ?
C19 C24 1.403(11) . ?
C19 C4 1.542(11) . ?
C4 C5 1.636(10) . ?
C5 C25 1.566(12) . ?
C5 C26 1.585(12) . ?
C21 C22 1.394(13) . ?
C21 H21 0.9300 . ?
C15 C16 1.360(14) . ?
C15 C14 1.376(12) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C24 C23 1.393(13) . ?
C24 H24 0.9300 . ?
C18 C17 1.417(12) . ?
C18 H18 0.9300 . ?
C12 C8 1.544(14) . ?
C12 H122 0.9600 . ?
C12 H121 0.9600 . ?
C12 H123 0.9600 . ?
C7 C10 1.518(15) . ?
C7 C9 1.527(13) . ?
C7 C8 1.536(13) . ?
C16 C17 1.362(14) . ?
C16 H16 0.9300 . ?
C22 C23 1.368(13) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C9 H91 0.9600 . ?
C9 H93 0.9600 . ?
C9 H92 0.9600 . ?
C11 C8 1.514(12) . ?
C11 H113 0.9600 . ?
C11 H112 0.9600 . ?
C11 H111 0.9600 . ?
C17 H17 0.9300 . ?
C10 H101 0.9600 . ?
C10 H102 0.9600 . ?
C10 H103 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 P1 O2 112.7(3) . . ?
O4 P1 O1 119.0(3) . . ?
O2 P1 O1 101.2(3) . . ?
O4 P1 O3 113.4(3) . . ?
O2 P1 O3 109.6(3) . . ?
O1 P1 O3 99.6(3) . . ?
C3 O2 P1 121.0(4) . . ?
C5 O6 H6 139(6) . . ?
C4 O7 H7 105(5) . . ?
C8 O3 P1 110.3(4) . . ?
C7 O1 P1 109.6(5) . . ?
C18 C13 C14 117.7(7) . . ?
C18 C13 C3 117.8(7) . . ?
C14 C13 C3 124.0(7) . . ?
C21 C20 C19 120.6(8) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
O2 C3 C13 106.8(5) . . ?
O2 C3 C4 106.4(5) . . ?
C13 C3 C4 115.7(6) . . ?
O2 C3 H3 109.3 . . ?
C13 C3 H3 109.3 . . ?
C4 C3 H3 109.3 . . ?
C20 C19 C24 118.5(7) . . ?
C20 C19 C4 122.4(7) . . ?
C24 C19 C4 119.0(7) . . ?
O7 C4 C19 108.3(6) . . ?
O7 C4 C3 111.0(5) . . ?
C19 C4 C3 106.2(6) . . ?
O7 C4 C5 108.0(5) . . ?
C19 C4 C5 110.2(5) . . ?
C3 C4 C5 113.0(6) . . ?
O6 C5 C25 108.2(6) . . ?
O6 C5 C26 103.5(6) . . ?
C25 C5 C26 107.2(6) . . ?
O6 C5 C4 114.0(6) . . ?
C25 C5 C4 113.8(6) . . ?
C26 C5 C4 109.5(6) . . ?
F4 C26 F5 107.4(8) . . ?
F4 C26 F6 108.1(7) . . ?
F5 C26 F6 106.1(7) . . ?
F4 C26 C5 111.6(7) . . ?
F5 C26 C5 113.0(7) . . ?
F6 C26 C5 110.4(7) . . ?
C20 C21 C22 121.4(8) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C16 C15 C14 118.6(9) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
F1 C25 F2 108.7(7) . . ?
F1 C25 F3 107.1(7) . . ?
F2 C25 F3 105.6(7) . . ?
F1 C25 C5 114.6(7) . . ?
F2 C25 C5 110.4(7) . . ?
F3 C25 C5 110.0(6) . . ?
C15 C14 C13 122.3(9) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C23 C24 C19 120.0(8) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?
C13 C18 C17 120.9(8) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C8 C12 H122 109.5 . . ?
C8 C12 H121 109.5 . . ?
H122 C12 H121 109.5 . . ?
C8 C12 H123 109.5 . . ?
H122 C12 H123 109.5 . . ?
H121 C12 H123 109.5 . . ?
O1 C7 C10 107.0(7) . . ?
O1 C7 C9 106.1(7) . . ?
C10 C7 C9 109.4(9) . . ?
O1 C7 C8 103.6(6) . . ?
C10 C7 C8 114.7(9) . . ?
C9 C7 C8 115.1(8) . . ?
C15 C16 C17 122.4(9) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C23 C22 C21 118.3(8) . . ?
C23 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?
C22 C23 C24 121.1(9) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C7 C9 H91 109.5 . . ?
C7 C9 H93 109.5 . . ?
H91 C9 H93 109.5 . . ?
C7 C9 H92 109.5 . . ?
H91 C9 H92 109.5 . . ?
H93 C9 H92 109.5 . . ?
C8 C11 H113 109.5 . . ?
C8 C11 H112 109.5 . . ?
H113 C11 H112 109.5 . . ?
C8 C11 H111 109.5 . . ?
H113 C11 H111 109.5 . . ?
H112 C11 H111 109.5 . . ?
O3 C8 C11 106.3(7) . . ?
O3 C8 C7 103.3(6) . . ?
C11 C8 C7 115.4(9) . . ?
O3 C8 C12 106.0(7) . . ?
C11 C8 C12 111.5(9) . . ?
C7 C8 C12 113.3(8) . . ?
C16 C17 C18 118.1(9) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C7 C10 H101 109.5 . . ?
C7 C10 H102 109.5 . . ?
H101 C10 H102 109.5 . . ?
C7 C10 H103 109.5 . . ?
H101 C10 H103 109.5 . . ?
H102 C10 H103 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 P1 O2 C3 -30.9(6) . . . . ?
O1 P1 O2 C3 -159.1(5) . . . . ?
O3 P1 O2 C3 96.4(5) . . . . ?
O4 P1 O3 C8 -138.6(5) . . . . ?
O2 P1 O3 C8 94.5(5) . . . . ?
O1 P1 O3 C8 -11.1(6) . . . . ?
O4 P1 O1 C7 110.7(6) . . . . ?
O2 P1 O1 C7 -125.3(5) . . . . ?
O3 P1 O1 C7 -12.9(6) . . . . ?
P1 O2 C3 C13 -72.7(7) . . . . ?
P1 O2 C3 C4 163.2(4) . . . . ?
C18 C13 C3 O2 110.2(7) . . . . ?
C14 C13 C3 O2 -62.0(9) . . . . ?
C18 C13 C3 C4 -131.6(7) . . . . ?
C14 C13 C3 C4 56.2(9) . . . . ?
C21 C20 C19 C24 -1.4(11) . . . . ?
C21 C20 C19 C4 -178.2(7) . . . . ?
C20 C19 C4 O7 175.3(6) . . . . ?
C24 C19 C4 O7 -1.4(9) . . . . ?
C20 C19 C4 C3 55.9(8) . . . . ?
C24 C19 C4 C3 -120.8(7) . . . . ?
C20 C19 C4 C5 -66.8(9) . . . . ?
C24 C19 C4 C5 116.5(7) . . . . ?
O2 C3 C4 O7 46.0(7) . . . . ?
C13 C3 C4 O7 -72.3(7) . . . . ?
O2 C3 C4 C19 163.6(5) . . . . ?
C13 C3 C4 C19 45.2(7) . . . . ?
O2 C3 C4 C5 -75.4(6) . . . . ?
C13 C3 C4 C5 166.2(5) . . . . ?
O7 C4 C5 O6 165.2(6) . . . . ?
C19 C4 C5 O6 47.0(8) . . . . ?
C3 C4 C5 O6 -71.6(8) . . . . ?
O7 C4 C5 C25 -70.1(8) . . . . ?
C19 C4 C5 C25 171.7(7) . . . . ?
C3 C4 C5 C25 53.1(8) . . . . ?
O7 C4 C5 C26 49.8(7) . . . . ?
C19 C4 C5 C26 -68.3(7) . . . . ?
C3 C4 C5 C26 173.0(6) . . . . ?
O6 C5 C26 F4 159.7(7) . . . . ?
C25 C5 C26 F4 45.5(9) . . . . ?
C4 C5 C26 F4 -78.4(8) . . . . ?
O6 C5 C26 F5 -79.1(8) . . . . ?
C25 C5 C26 F5 166.7(6) . . . . ?
C4 C5 C26 F5 42.8(8) . . . . ?
O6 C5 C26 F6 39.4(8) . . . . ?
C25 C5 C26 F6 -74.8(8) . . . . ?
C4 C5 C26 F6 161.3(6) . . . . ?
C19 C20 C21 C22 1.4(12) . . . . ?
O6 C5 C25 F1 175.0(7) . . . . ?
C26 C5 C25 F1 -74.0(8) . . . . ?
C4 C5 C25 F1 47.3(10) . . . . ?
O6 C5 C25 F2 51.9(8) . . . . ?
C26 C5 C25 F2 162.9(6) . . . . ?
C4 C5 C25 F2 -75.8(8) . . . . ?
O6 C5 C25 F3 -64.3(9) . . . . ?
C26 C5 C25 F3 46.7(9) . . . . ?
C4 C5 C25 F3 168.0(6) . . . . ?
C16 C15 C14 C13 -0.6(14) . . . . ?
C18 C13 C14 C15 0.2(13) . . . . ?
C3 C13 C14 C15 172.3(8) . . . . ?
C20 C19 C24 C23 0.8(12) . . . . ?
C4 C19 C24 C23 177.7(8) . . . . ?
C14 C13 C18 C17 1.0(12) . . . . ?
C3 C13 C18 C17 -171.6(8) . . . . ?
P1 O1 C7 C10 -90.2(8) . . . . ?
P1 O1 C7 C9 153.0(7) . . . . ?
P1 O1 C7 C8 31.4(8) . . . . ?
C14 C15 C16 C17 -0.1(15) . . . . ?
C20 C21 C22 C23 -0.7(13) . . . . ?
C21 C22 C23 C24 0.2(15) . . . . ?
C19 C24 C23 C22 -0.2(14) . . . . ?
P1 O3 C8 C11 152.1(8) . . . . ?
P1 O3 C8 C7 30.2(7) . . . . ?
P1 O3 C8 C12 -89.2(7) . . . . ?
O1 C7 C8 O3 -37.0(8) . . . . ?
C10 C7 C8 O3 79.4(9) . . . . ?
C9 C7 C8 O3 -152.3(7) . . . . ?
O1 C7 C8 C11 -152.5(8) . . . . ?
C10 C7 C8 C11 -36.2(11) . . . . ?
C9 C7 C8 C11 92.1(10) . . . . ?
O1 C7 C8 C12 77.2(8) . . . . ?
C10 C7 C8 C12 -166.4(8) . . . . ?
C9 C7 C8 C12 -38.1(10) . . . . ?
C15 C16 C17 C18 1.3(15) . . . . ?
C13 C18 C17 C16 -1.7(13) . . . . ?

_refine_diff_density_max         0.654
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.247

####################################################################### 
# 
# 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_k51_fin
_database_code_depnum_ccdc_archive 'CCDC 1474603'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 F6 O5 P'
_chemical_formula_sum            'C23 H23 F6 O5 P'
_chemical_formula_weight         524.38

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

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

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

_cell_length_a                   9.485(6)
_cell_length_b                   11.002(7)
_cell_length_c                   12.115(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.517(8)
_cell_angle_gamma                90
_cell_volume                     1238.8(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3685
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      21.80

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4139
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            12827
_diffrn_reflns_av_unetI/netI     0.0825
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.715
_diffrn_reflns_theta_max         26.000
_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 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.939
_reflns_number_total             4529
_reflns_number_gt                2921
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_max     0.859
_reflns_Friedel_fraction_full    0.872

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1250P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1038 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4529
_refine_ls_number_parameters     320
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.2021
_refine_ls_wR_factor_gt          0.1629
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.37274(19) 0.86985(17) 0.69231(14) 0.0448(5) Uani 1 1 d . . . . .
O7 O 0.2948(5) 0.8979(4) 0.8055(4) 0.0451(11) Uani 1 1 d . . . . .
O3 O 0.5019(5) 0.8140(5) 0.7810(4) 0.0537(13) Uani 1 1 d . . . . .
O5 O 0.0934(5) 0.9061(4) 0.6669(4) 0.0512(13) Uani 1 1 d . . . . .
O1 O 0.4393(5) 0.8249(5) 0.5867(4) 0.0554(14) Uani 1 1 d . . . . .
O2 O 0.3679(5) 1.0134(4) 0.6625(4) 0.0470(11) Uani 1 1 d . . . . .
F5 F 0.1853(6) 0.9469(6) 0.4615(4) 0.0856(16) Uani 1 1 d . . . . .
F4 F 0.1980(6) 0.7550(6) 0.4367(4) 0.0891(18) Uani 1 1 d . . . . .
C4 C 0.1835(7) 0.9757(6) 0.7597(6) 0.0424(16) Uani 1 1 d . . . . .
C6 C 0.1802(7) 0.8218(7) 0.6215(6) 0.0476(17) Uani 1 1 d . . . . .
F6 F -0.0005(6) 0.8348(7) 0.4571(5) 0.101(2) Uani 1 1 d . . . . .
C19 C 0.0878(7) 1.0141(7) 0.8385(6) 0.0492(17) Uani 1 1 d . . . . .
F2 F 0.2207(7) 0.6090(5) 0.6167(7) 0.109(2) Uani 1 1 d . . . . .
C14 C 0.4546(9) 1.1529(8) 0.8675(7) 0.059(2) Uani 1 1 d . . . . .
H14 H 0.4983 1.0770 0.8696 0.071 Uiso 1 1 calc R U . . .
C3 C 0.2596(7) 1.0790(6) 0.7072(6) 0.0429(15) Uani 1 1 d . . . . .
H3 H 0.1915 1.1169 0.6453 0.051 Uiso 1 1 calc R U . . .
F1 F 0.1618(9) 0.6776(6) 0.7623(6) 0.125(3) Uani 1 1 d . . . . .
C13 C 0.3298(7) 1.1761(7) 0.7886(6) 0.0457(16) Uani 1 1 d . . . . .
C8 C 0.6166(8) 0.7526(8) 0.7347(7) 0.062(2) Uani 1 1 d . . . . .
C16 C 0.4537(10) 1.3532(9) 0.9397(7) 0.075(3) Uani 1 1 d . . . . .
H16 H 0.4944 1.4124 0.9911 0.090 Uiso 1 1 calc R U . . .
C20 C 0.1121(9) 0.9756(10) 0.9475(7) 0.071(2) Uani 1 1 d . . . . .
H20 H 0.1872 0.9221 0.9741 0.085 Uiso 1 1 calc R U . . .
C25 C 0.1410(9) 0.6923(8) 0.6531(9) 0.065(2) Uani 1 1 d . . . . .
F3 F 0.0067(6) 0.6631(6) 0.6135(9) 0.132(3) Uani 1 1 d . . . . .
C26 C 0.1409(8) 0.8385(9) 0.4949(7) 0.066(2) Uani 1 1 d . . . . .
C24 C -0.0241(9) 1.0934(8) 0.8002(8) 0.064(2) Uani 1 1 d . . . . .
H24 H -0.0412 1.1201 0.7259 0.077 Uiso 1 1 calc R U . . .
C11 C 0.7582(9) 0.7859(11) 0.8128(8) 0.084(3) Uani 1 1 d . . . . .
H112 H 0.7690 0.8727 0.8153 0.126 Uiso 1 1 calc R U . . .
H113 H 0.8367 0.7501 0.7851 0.126 Uiso 1 1 calc R U . . .
H111 H 0.7581 0.7558 0.8872 0.126 Uiso 1 1 calc R U . . .
C15 C 0.5139(10) 1.2417(9) 0.9426(8) 0.071(2) Uani 1 1 d . . . . .
H15 H 0.5965 1.2247 0.9960 0.085 Uiso 1 1 calc R U . . .
C10 C 0.6310(11) 0.7178(11) 0.5261(10) 0.092(3) Uani 1 1 d . . . . .
H101 H 0.5793 0.6431 0.5279 0.137 Uiso 1 1 calc R U . . .
H103 H 0.7325 0.7016 0.5411 0.137 Uiso 1 1 calc R U . . .
H102 H 0.6033 0.7544 0.4530 0.137 Uiso 1 1 calc R U . . .
C23 C -0.1107(10) 1.1331(10) 0.8719(10) 0.079(3) Uani 1 1 d . . . . .
H23 H -0.1866 1.1858 0.8459 0.095 Uiso 1 1 calc R U . . .
C18 C 0.2700(10) 1.2917(8) 0.7862(7) 0.066(2) Uani 1 1 d . . . . .
H18 H 0.1871 1.3097 0.7335 0.079 Uiso 1 1 calc R U . . .
C17 C 0.3317(11) 1.3790(10) 0.8604(9) 0.088(3) Uani 1 1 d . . . . .
H17 H 0.2913 1.4562 0.8574 0.106 Uiso 1 1 calc R U . . .
C7 C 0.5960(8) 0.8044(9) 0.6154(7) 0.063(2) Uani 1 1 d . . . . .
C22 C -0.0844(11) 1.0947(12) 0.9808(9) 0.088(3) Uani 1 1 d . . . . .
H22 H -0.1419 1.1226 1.0293 0.105 Uiso 1 1 calc R U . . .
C9 C 0.6701(9) 0.9270(9) 0.6074(9) 0.076(3) Uani 1 1 d . . . . .
H93 H 0.6359 0.9617 0.5342 0.114 Uiso 1 1 calc R U . . .
H92 H 0.7722 0.9152 0.6190 0.114 Uiso 1 1 calc R U . . .
H91 H 0.6484 0.9810 0.6640 0.114 Uiso 1 1 calc R U . . .
C12 C 0.5873(11) 0.6171(9) 0.7425(12) 0.098(4) Uani 1 1 d . . . . .
H123 H 0.5751 0.5977 0.8172 0.147 Uiso 1 1 calc R U . . .
H121 H 0.6671 0.5719 0.7257 0.147 Uiso 1 1 calc R U . . .
H122 H 0.5014 0.5963 0.6893 0.147 Uiso 1 1 calc R U . . .
C21 C 0.0237(12) 1.0168(12) 1.0194(9) 0.092(3) Uani 1 1 d . . . . .
H21 H 0.0397 0.9904 1.0937 0.110 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 O3 1.584(5) . ?
P1 O1 1.613(5) . ?
P1 O2 1.619(5) . ?
P1 O7 1.711(5) . ?
P1 C6 1.930(7) . ?
O7 C4 1.387(8) . ?
O3 C8 1.482(9) . ?
O5 C6 1.421(8) . ?
O5 C4 1.482(8) . ?
O1 C7 1.474(9) . ?
O2 C3 1.446(8) . ?
F5 C26 1.354(11) . ?
F4 C26 1.336(10) . ?
C4 C19 1.503(10) . ?
C4 C3 1.550(10) . ?
C6 C26 1.516(12) . ?
C6 C25 1.540(12) . ?
F6 C26 1.329(9) . ?
C19 C20 1.362(11) . ?
C19 C24 1.381(11) . ?
F2 C25 1.319(10) . ?
C14 C15 1.376(12) . ?
C14 C13 1.388(10) . ?
C3 C13 1.515(10) . ?
F1 C25 1.309(11) . ?
C13 C18 1.391(11) . ?
C8 C12 1.523(14) . ?
C8 C11 1.525(12) . ?
C8 C7 1.529(13) . ?
C16 C15 1.350(14) . ?
C16 C17 1.378(13) . ?
C20 C21 1.399(13) . ?
C25 F3 1.308(10) . ?
C24 C23 1.380(12) . ?
C10 C7 1.527(12) . ?
C23 C22 1.360(15) . ?
C18 C17 1.364(13) . ?
C7 C9 1.534(13) . ?
C22 C21 1.347(15) . ?

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
O3 P1 O1 92.7(3) . . ?
O3 P1 O2 120.9(3) . . ?
O1 P1 O2 96.9(3) . . ?
O3 P1 O7 85.7(2) . . ?
O1 P1 O7 172.3(3) . . ?
O2 P1 O7 90.3(2) . . ?
O3 P1 C6 136.9(3) . . ?
O1 P1 C6 92.8(3) . . ?
O2 P1 C6 100.7(3) . . ?
O7 P1 C6 83.3(3) . . ?
C4 O7 P1 101.9(4) . . ?
C8 O3 P1 116.5(5) . . ?
C6 O5 C4 109.9(5) . . ?
C7 O1 P1 113.3(4) . . ?
C3 O2 P1 113.2(4) . . ?
O7 C4 O5 105.2(5) . . ?
O7 C4 C19 115.3(6) . . ?
O5 C4 C19 107.3(5) . . ?
O7 C4 C3 103.7(5) . . ?
O5 C4 C3 108.3(5) . . ?
C19 C4 C3 116.4(5) . . ?
O5 C6 C26 105.6(6) . . ?
O5 C6 C25 108.7(6) . . ?
C26 C6 C25 109.9(7) . . ?
O5 C6 P1 102.6(4) . . ?
C26 C6 P1 115.9(5) . . ?
C25 C6 P1 113.4(6) . . ?
C20 C19 C24 119.5(7) . . ?
C20 C19 C4 121.4(7) . . ?
C24 C19 C4 119.0(7) . . ?
C15 C14 C13 120.3(8) . . ?
O2 C3 C13 110.1(5) . . ?
O2 C3 C4 102.2(5) . . ?
C13 C3 C4 115.5(6) . . ?
C14 C13 C18 118.1(7) . . ?
C14 C13 C3 121.5(6) . . ?
C18 C13 C3 120.4(6) . . ?
O3 C8 C12 105.4(7) . . ?
O3 C8 C11 106.2(7) . . ?
C12 C8 C11 110.2(8) . . ?
O3 C8 C7 102.9(6) . . ?
C12 C8 C7 115.6(8) . . ?
C11 C8 C7 115.3(8) . . ?
C15 C16 C17 119.8(9) . . ?
C19 C20 C21 119.7(9) . . ?
F3 C25 F1 106.3(8) . . ?
F3 C25 F2 106.7(7) . . ?
F1 C25 F2 105.7(9) . . ?
F3 C25 C6 113.7(8) . . ?
F1 C25 C6 111.8(7) . . ?
F2 C25 C6 112.2(7) . . ?
F6 C26 F4 106.6(7) . . ?
F6 C26 F5 106.1(8) . . ?
F4 C26 F5 105.4(7) . . ?
F6 C26 C6 111.9(7) . . ?
F4 C26 C6 114.0(8) . . ?
F5 C26 C6 112.4(6) . . ?
C23 C24 C19 120.2(9) . . ?
C16 C15 C14 120.8(8) . . ?
C22 C23 C24 119.7(10) . . ?
C17 C18 C13 120.7(8) . . ?
C18 C17 C16 120.3(9) . . ?
O1 C7 C10 106.3(7) . . ?
O1 C7 C8 102.3(6) . . ?
C10 C7 C8 115.7(9) . . ?
O1 C7 C9 107.7(7) . . ?
C10 C7 C9 109.7(8) . . ?
C8 C7 C9 114.4(7) . . ?
C21 C22 C23 120.9(9) . . ?
C22 C21 C20 120.0(10) . . ?

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
O3 P1 O7 C4 167.1(4) . . . . ?
O2 P1 O7 C4 46.1(4) . . . . ?
C6 P1 O7 C4 -54.6(4) . . . . ?
O1 P1 O3 C8 0.7(5) . . . . ?
O2 P1 O3 C8 -99.0(6) . . . . ?
O7 P1 O3 C8 173.2(5) . . . . ?
C6 P1 O3 C8 97.7(6) . . . . ?
O3 P1 O1 C7 -23.0(6) . . . . ?
O2 P1 O1 C7 98.6(6) . . . . ?
C6 P1 O1 C7 -160.2(6) . . . . ?
O3 P1 O2 C3 -108.3(4) . . . . ?
O1 P1 O2 C3 154.3(4) . . . . ?
O7 P1 O2 C3 -23.2(4) . . . . ?
C6 P1 O2 C3 60.1(5) . . . . ?
P1 O7 C4 O5 59.5(5) . . . . ?
P1 O7 C4 C19 177.4(5) . . . . ?
P1 O7 C4 C3 -54.1(5) . . . . ?
C6 O5 C4 O7 -29.4(7) . . . . ?
C6 O5 C4 C19 -152.7(6) . . . . ?
C6 O5 C4 C3 81.0(6) . . . . ?
C4 O5 C6 C26 -131.6(6) . . . . ?
C4 O5 C6 C25 110.5(6) . . . . ?
C4 O5 C6 P1 -9.8(6) . . . . ?
O7 C4 C19 C20 1.0(10) . . . . ?
O5 C4 C19 C20 117.8(8) . . . . ?
C3 C4 C19 C20 -120.8(8) . . . . ?
O7 C4 C19 C24 178.8(7) . . . . ?
O5 C4 C19 C24 -64.4(8) . . . . ?
C3 C4 C19 C24 57.0(9) . . . . ?
P1 O2 C3 C13 119.0(5) . . . . ?
P1 O2 C3 C4 -4.2(6) . . . . ?
O7 C4 C3 O2 37.9(6) . . . . ?
O5 C4 C3 O2 -73.5(6) . . . . ?
C19 C4 C3 O2 165.6(6) . . . . ?
O7 C4 C3 C13 -81.6(7) . . . . ?
O5 C4 C3 C13 167.0(5) . . . . ?
C19 C4 C3 C13 46.1(8) . . . . ?
C15 C14 C13 C18 1.7(12) . . . . ?
C15 C14 C13 C3 -178.2(8) . . . . ?
O2 C3 C13 C14 -43.1(9) . . . . ?
C4 C3 C13 C14 71.9(9) . . . . ?
O2 C3 C13 C18 137.0(7) . . . . ?
C4 C3 C13 C18 -107.9(8) . . . . ?
P1 O3 C8 C12 -101.9(8) . . . . ?
P1 O3 C8 C11 141.2(7) . . . . ?
P1 O3 C8 C7 19.6(8) . . . . ?
C24 C19 C20 C21 -0.1(13) . . . . ?
C4 C19 C20 C21 177.7(8) . . . . ?
O5 C6 C25 F3 60.8(10) . . . . ?
C26 C6 C25 F3 -54.3(10) . . . . ?
P1 C6 C25 F3 174.3(7) . . . . ?
O5 C6 C25 F1 -59.5(9) . . . . ?
C26 C6 C25 F1 -174.6(8) . . . . ?
P1 C6 C25 F1 54.0(9) . . . . ?
O5 C6 C25 F2 -178.0(7) . . . . ?
C26 C6 C25 F2 66.9(9) . . . . ?
P1 C6 C25 F2 -64.5(9) . . . . ?
O5 C6 C26 F6 -50.4(9) . . . . ?
C25 C6 C26 F6 66.6(9) . . . . ?
P1 C6 C26 F6 -163.3(6) . . . . ?
O5 C6 C26 F4 -171.4(6) . . . . ?
C25 C6 C26 F4 -54.4(9) . . . . ?
P1 C6 C26 F4 75.7(8) . . . . ?
O5 C6 C26 F5 68.8(8) . . . . ?
C25 C6 C26 F5 -174.2(7) . . . . ?
P1 C6 C26 F5 -44.1(8) . . . . ?
C20 C19 C24 C23 -0.1(12) . . . . ?
C4 C19 C24 C23 -177.9(7) . . . . ?
C17 C16 C15 C14 -0.3(16) . . . . ?
C13 C14 C15 C16 -1.2(15) . . . . ?
C19 C24 C23 C22 0.6(15) . . . . ?
C14 C13 C18 C17 -0.8(13) . . . . ?
C3 C13 C18 C17 179.1(9) . . . . ?
C13 C18 C17 C16 -0.7(17) . . . . ?
C15 C16 C17 C18 1.3(17) . . . . ?
P1 O1 C7 C10 158.0(7) . . . . ?
P1 O1 C7 C8 36.3(8) . . . . ?
P1 O1 C7 C9 -84.5(7) . . . . ?
O3 C8 C7 O1 -31.8(8) . . . . ?
C12 C8 C7 O1 82.5(8) . . . . ?
C11 C8 C7 O1 -146.9(7) . . . . ?
O3 C8 C7 C10 -146.8(7) . . . . ?
C12 C8 C7 C10 -32.5(11) . . . . ?
C11 C8 C7 C10 98.1(10) . . . . ?
O3 C8 C7 C9 84.3(7) . . . . ?
C12 C8 C7 C9 -161.4(7) . . . . ?
C11 C8 C7 C9 -30.8(10) . . . . ?
C24 C23 C22 C21 -1.0(17) . . . . ?
C23 C22 C21 C20 0.9(18) . . . . ?
C19 C20 C21 C22 -0.3(16) . . . . ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.111

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_k53n_fin1
_database_code_depnum_ccdc_archive 'CCDC 1474604'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 F6 O5 P'
_chemical_formula_sum            'C23 H23 F6 O5 P'
_chemical_formula_weight         524.38

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   12.650(5)
_cell_length_b                   16.695(6)
_cell_length_c                   22.988(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4855(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7418
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      28.52

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             2160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6390
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            28292
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.206
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4766
_reflns_number_gt                2856
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²+0.2000P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4766
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1825
_refine_ls_wR_factor_gt          0.1426
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.011

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 0.01153(6) 0.34055(4) 0.10125(3) 0.0391(2) Uani 1 1 d . . . . .
O7 O 0.00289(14) 0.24197(11) 0.11906(8) 0.0381(5) Uani 1 1 d . . . . .
O6 O 0.01952(16) 0.31272(12) 0.03264(8) 0.0449(5) Uani 1 1 d . . . . .
O2 O 0.13101(15) 0.34323(11) 0.12480(9) 0.0432(5) Uani 1 1 d . . . . .
O1 O 0.01450(17) 0.43464(12) 0.08329(10) 0.0508(6) Uani 1 1 d . . . . .
F2 F 0.21831(16) 0.33058(12) 0.00901(9) 0.0672(6) Uani 1 1 d . . . . .
C4 C 0.0961(2) 0.21120(17) 0.09387(12) 0.0367(7) Uani 1 1 d . . . . .
F5 F -0.07110(17) 0.15315(13) 0.02415(9) 0.0705(6) Uani 1 1 d . . . . .
F1 F 0.25392(16) 0.20609(12) -0.00080(9) 0.0700(6) Uani 1 1 d . . . . .
O3 O -0.09218(18) 0.35191(12) 0.13883(10) 0.0519(6) Uani 1 1 d . . . . .
F6 F 0.0656(2) 0.11845(13) -0.02537(9) 0.0804(7) Uani 1 1 d . . . . .
C20 C 0.0274(3) 0.07798(19) 0.12828(14) 0.0497(8) Uani 1 1 d . . . . .
H20 H -0.0369 0.1025 0.1365 0.060 Uiso 1 1 calc R U . . .
C19 C 0.1091(2) 0.12264(17) 0.10468(12) 0.0405(7) Uani 1 1 d . . . . .
F3 F 0.1594(2) 0.26670(15) -0.06440(8) 0.0845(7) Uani 1 1 d . . . . .
F4 F -0.0339(2) 0.21563(14) -0.05382(9) 0.0822(7) Uani 1 1 d . . . . .
C5 C 0.0773(2) 0.24004(18) 0.02757(12) 0.0427(7) Uani 1 1 d . . . . .
C13 C 0.2097(2) 0.24039(18) 0.18562(13) 0.0444(8) Uani 1 1 d . . . . .
C24 C 0.2052(3) 0.0843(2) 0.09342(14) 0.0525(8) Uani 1 1 d . . . . .
H24 H 0.2615 0.1132 0.0780 0.063 Uiso 1 1 calc R U . . .
C3 C 0.1813(2) 0.26518(17) 0.12446(13) 0.0410(7) Uani 1 1 d . . . . .
H3 H 0.2454 0.2672 0.1005 0.049 Uiso 1 1 calc R U . . .
C7 C -0.0768(3) 0.4810(2) 0.09892(17) 0.0610(10) Uani 1 1 d . . . . .
C14 C 0.1403(3) 0.2500(2) 0.23139(15) 0.0573(9) Uani 1 1 d . . . . .
H14 H 0.0732 0.2709 0.2247 0.069 Uiso 1 1 calc R U . . .
C23 C 0.2168(3) 0.0040(2) 0.10503(16) 0.0623(10) Uani 1 1 d . . . . .
H23 H 0.2809 -0.0210 0.0972 0.075 Uiso 1 1 calc R U . . .
C8 C -0.1229(3) 0.4349(2) 0.15054(16) 0.0597(9) Uani 1 1 d . . . . .
C10 C -0.0418(4) 0.5657(2) 0.1091(2) 0.0826(12) Uani 1 1 d . . . . .
H111 H 0.0146 0.5663 0.1370 0.124 Uiso 1 1 calc R U . . .
H112 H -0.1001 0.5966 0.1235 0.124 Uiso 1 1 calc R U . . .
H113 H -0.0174 0.5884 0.0731 0.124 Uiso 1 1 calc R U . . .
C9 C -0.1514(4) 0.4806(3) 0.0456(2) 0.0870(13) Uani 1 1 d . . . . .
H122 H -0.1152 0.5028 0.0126 0.131 Uiso 1 1 calc R U . . .
H123 H -0.2130 0.5123 0.0539 0.131 Uiso 1 1 calc R U . . .
H121 H -0.1724 0.4266 0.0371 0.131 Uiso 1 1 calc R U . . .
C11 C -0.2396(4) 0.4376(3) 0.1584(3) 0.131(3) Uani 1 1 d . . . . .
H102 H -0.2733 0.4128 0.1256 0.197 Uiso 1 1 calc R U . . .
H103 H -0.2622 0.4924 0.1612 0.197 Uiso 1 1 calc R U . . .
H101 H -0.2585 0.4095 0.1933 0.197 Uiso 1 1 calc R U . . .
C22 C 0.1354(3) -0.0397(2) 0.12782(17) 0.0638(10) Uani 1 1 d . . . . .
H22 H 0.1440 -0.0940 0.1353 0.077 Uiso 1 1 calc R U . . .
C21 C 0.0406(3) -0.0027(2) 0.13972(16) 0.0617(9) Uani 1 1 d . . . . .
H21 H -0.0149 -0.0321 0.1555 0.074 Uiso 1 1 calc R U . . .
C15 C 0.1702(4) 0.2286(2) 0.28773(16) 0.0713(11) Uani 1 1 d . . . . .
H15 H 0.1227 0.2346 0.3183 0.086 Uiso 1 1 calc R U . . .
C18 C 0.3094(3) 0.2105(2) 0.19709(16) 0.0637(10) Uani 1 1 d . . . . .
H18 H 0.3579 0.2047 0.1670 0.076 Uiso 1 1 calc R U . . .
C17 C 0.3375(4) 0.1893(3) 0.2532(2) 0.0851(13) Uani 1 1 d . . . . .
H17 H 0.4042 0.1681 0.2604 0.102 Uiso 1 1 calc R U . . .
C16 C 0.2679(4) 0.1991(3) 0.29813(18) 0.0786(13) Uani 1 1 d . . . . .
H16 H 0.2877 0.1855 0.3358 0.094 Uiso 1 1 calc R U . . .
C26 C 0.0088(3) 0.1812(2) -0.00730(16) 0.0589(9) Uani 1 1 d . . . . .
C25 C 0.1779(3) 0.2616(2) -0.00736(14) 0.0546(9) Uani 1 1 d . . . . .
C12 C -0.0634(6) 0.4553(3) 0.2073(2) 0.124(2) Uani 1 1 d . . . . .
H12A H -0.0728 0.4127 0.2348 0.186 Uiso 1 1 calc R U . . .
H12B H -0.0910 0.5042 0.2232 0.186 Uiso 1 1 calc R U . . .
H12C H 0.0105 0.4618 0.1990 0.186 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 O3 1.582(2) . ?
P1 O2 1.606(2) . ?
P1 O1 1.625(2) . ?
P1 O6 1.647(2) . ?
P1 O7 1.700(2) . ?
O7 C4 1.410(3) . ?
O6 C5 1.421(3) . ?
O2 C3 1.450(3) . ?
O1 C7 1.436(4) . ?
F2 C25 1.316(4) . ?
C4 C19 1.508(4) . ?
C4 C3 1.572(4) . ?
C4 C5 1.616(4) . ?
F5 C26 1.328(4) . ?
F1 C25 1.343(4) . ?
O3 C8 1.465(4) . ?
F6 C26 1.337(4) . ?
C20 C21 1.382(5) . ?
C20 C19 1.384(4) . ?
C20 H20 0.9300 . ?
C19 C24 1.398(4) . ?
F3 C25 1.335(4) . ?
F4 C26 1.329(4) . ?
C5 C26 1.536(5) . ?
C5 C25 1.547(5) . ?
C13 C18 1.382(5) . ?
C13 C14 1.380(5) . ?
C13 C3 1.509(4) . ?
C24 C23 1.376(5) . ?
C24 H24 0.9300 . ?
C3 H3 0.9800 . ?
C7 C10 1.498(5) . ?
C7 C8 1.530(5) . ?
C7 C9 1.548(6) . ?
C14 C15 1.396(5) . ?
C14 H14 0.9300 . ?
C23 C22 1.365(5) . ?
C23 H23 0.9300 . ?
C8 C11 1.487(6) . ?
C8 C12 1.544(6) . ?
C10 H111 0.9600 . ?
C10 H112 0.9600 . ?
C10 H113 0.9600 . ?
C9 H122 0.9600 . ?
C9 H123 0.9600 . ?
C9 H121 0.9600 . ?
C11 H102 0.9600 . ?
C11 H103 0.9600 . ?
C11 H101 0.9600 . ?
C22 C21 1.378(5) . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
C15 C16 1.351(6) . ?
C15 H15 0.9300 . ?
C18 C17 1.384(5) . ?
C18 H18 0.9300 . ?
C17 C16 1.367(6) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
O3 P1 O2 126.36(13) . . ?
O3 P1 O1 92.41(11) . . ?
O2 P1 O1 92.12(11) . . ?
O3 P1 O6 127.41(12) . . ?
O2 P1 O6 105.84(11) . . ?
O1 P1 O6 91.61(11) . . ?
O3 P1 O7 86.05(10) . . ?
O2 P1 O7 90.36(10) . . ?
O1 P1 O7 177.52(11) . . ?
O6 P1 O7 87.79(10) . . ?
C4 O7 P1 101.55(16) . . ?
C5 O6 P1 110.54(16) . . ?
C3 O2 P1 112.72(17) . . ?
C7 O1 P1 116.1(2) . . ?
O7 C4 C19 112.4(2) . . ?
O7 C4 C3 100.4(2) . . ?
C19 C4 C3 114.4(2) . . ?
O7 C4 C5 99.0(2) . . ?
C19 C4 C5 117.6(2) . . ?
C3 C4 C5 110.6(2) . . ?
C8 O3 P1 115.7(2) . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C19 C24 118.3(3) . . ?
C20 C19 C4 120.7(3) . . ?
C24 C19 C4 120.9(3) . . ?
O6 C5 C26 107.4(2) . . ?
O6 C5 C25 105.5(2) . . ?
C26 C5 C25 110.0(3) . . ?
O6 C5 C4 104.6(2) . . ?
C26 C5 C4 112.6(3) . . ?
C25 C5 C4 116.0(2) . . ?
C18 C13 C14 118.5(3) . . ?
C18 C13 C3 119.6(3) . . ?
C14 C13 C3 121.9(3) . . ?
C23 C24 C19 120.2(3) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
O2 C3 C13 110.2(2) . . ?
O2 C3 C4 102.5(2) . . ?
C13 C3 C4 115.0(2) . . ?
O2 C3 H3 109.6 . . ?
C13 C3 H3 109.6 . . ?
C4 C3 H3 109.6 . . ?
O1 C7 C10 108.1(3) . . ?
O1 C7 C8 103.3(3) . . ?
C10 C7 C8 117.8(3) . . ?
O1 C7 C9 106.9(3) . . ?
C10 C7 C9 107.9(3) . . ?
C8 C7 C9 112.3(3) . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C22 C23 C24 121.0(3) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
O3 C8 C11 108.3(3) . . ?
O3 C8 C7 103.4(2) . . ?
C11 C8 C7 117.2(4) . . ?
O3 C8 C12 103.5(3) . . ?
C11 C8 C12 112.0(4) . . ?
C7 C8 C12 111.0(4) . . ?
C7 C10 H111 109.5 . . ?
C7 C10 H112 109.5 . . ?
H111 C10 H112 109.5 . . ?
C7 C10 H113 109.5 . . ?
H111 C10 H113 109.5 . . ?
H112 C10 H113 109.5 . . ?
C7 C9 H122 109.5 . . ?
C7 C9 H123 109.5 . . ?
H122 C9 H123 109.5 . . ?
C7 C9 H121 109.5 . . ?
H122 C9 H121 109.5 . . ?
H123 C9 H121 109.5 . . ?
C8 C11 H102 109.5 . . ?
C8 C11 H103 109.5 . . ?
H102 C11 H103 109.5 . . ?
C8 C11 H101 109.5 . . ?
H102 C11 H101 109.5 . . ?
H103 C11 H101 109.5 . . ?
C23 C22 C21 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C20 C21 C22 120.3(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C13 C18 C17 120.3(4) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C16 C17 C18 120.6(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C15 C16 C17 119.9(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
F5 C26 F4 106.4(3) . . ?
F5 C26 F6 107.6(3) . . ?
F4 C26 F6 107.9(3) . . ?
F5 C26 C5 111.8(3) . . ?
F4 C26 C5 111.9(3) . . ?
F6 C26 C5 111.1(3) . . ?
F2 C25 F3 107.0(3) . . ?
F2 C25 F1 107.1(3) . . ?
F3 C25 F1 106.3(3) . . ?
F2 C25 C5 112.0(3) . . ?
F3 C25 C5 112.4(3) . . ?
F1 C25 C5 111.7(3) . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.612
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.121

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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 
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data_k66_f2
_database_code_depnum_ccdc_archive 'CCDC 1485824'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H15 F6 O6 P, 0.5(C6 H14 O2)'
_chemical_formula_sum            'C20 H22 F6 O7 P'
_chemical_melting_point          ?

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         519.34

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'

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

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

_cell_length_a                   18.721(8)
_cell_length_b                   13.944(6)
_cell_length_c                   8.706(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.489(8)
_cell_angle_gamma                90
_cell_volume                     2262.2(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1834
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      29.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   0.4996
_exptl_transmission_factor_max   0.7459
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.210
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Smart APEX II'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11470
_diffrn_reflns_av_unetI/netI     0.2260
_diffrn_reflns_av_R_equivalents  0.1522
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.824
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4448
_reflns_number_gt                1673
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²+0.1401P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4448
_refine_ls_number_parameters     325
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2229
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.2372
_refine_ls_wR_factor_gt          0.1632
_refine_ls_goodness_of_fit_ref   0.899
_refine_ls_restrained_S_all      0.899
_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 0.14023(9) 0.82166(11) -0.00972(18) 0.0321(5) Uani 1 1 d . . . . .
O2 O 0.1881(2) 0.8922(3) 0.1001(4) 0.0308(10) Uani 1 1 d . . . . .
O4 O 0.1811(2) 0.7832(3) -0.1348(4) 0.0399(11) Uani 1 1 d . . . . .
F1 F 0.2995(2) 0.7655(2) 0.1661(4) 0.0527(11) Uani 1 1 d . . . . .
O6 O 0.2411(2) 1.0419(3) 0.2794(5) 0.0424(12) Uani 1 1 d . . . . .
H6 H 0.1938 1.0340 0.3012 0.051 Uiso 1 1 d R U . . .
O1 O 0.1130(3) 0.7484(3) 0.1027(5) 0.0467(13) Uani 1 1 d D . . . .
F5 F 0.3624(2) 1.0355(3) 0.4888(5) 0.0713(13) Uani 1 1 d . . . . .
F3 F 0.4001(2) 0.8350(3) 0.1435(5) 0.0658(12) Uani 1 1 d . . . . .
F6 F 0.4434(2) 0.9647(3) 0.3677(5) 0.0713(13) Uani 1 1 d . . . . .
O5 O 1.0651(3) -0.0286(4) 0.6669(5) 0.0489(13) Uani 1 1 d . . . . .
O7 O 0.2679(3) 0.8801(3) 0.4086(5) 0.0448(12) Uani 1 1 d . . . . .
O3 O 0.0704(2) 0.8741(3) -0.0723(5) 0.0414(12) Uani 1 1 d . . . . .
F2 F 0.3831(2) 0.7577(3) 0.3475(5) 0.0741(13) Uani 1 1 d . . . . .
C5 C 0.3222(3) 0.9086(4) 0.3146(7) 0.0341(16) Uani 1 1 d . . . . .
C13 C 0.2173(3) 1.0274(4) -0.0647(7) 0.0362(16) Uani 1 1 d . . . . .
F4 F 0.3964(2) 0.8931(3) 0.5534(4) 0.0753(14) Uani 1 1 d . . . . .
C3 C 0.2458(3) 0.9484(4) 0.0467(6) 0.0322(15) Uani 1 1 d . . . . .
H31 H 0.2772 0.9060 -0.0064 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2896(3) 0.9911(4) 0.1942(7) 0.0368(16) Uani 1 1 d . . . . .
C25 C 0.3518(4) 0.8187(5) 0.2416(8) 0.0458(18) Uani 1 1 d . . . . .
C19 C 0.3444(4) 1.0618(4) 0.1405(8) 0.0393(17) Uani 1 1 d . . . . .
C20 C 0.3912(4) 1.0380(5) 0.0319(8) 0.0482(19) Uani 1 1 d . . . . .
H20 H 0.3915 0.9754 -0.0051 0.058 Uiso 1 1 calc R U . . .
C6 C 0.9943(3) -0.0101(4) 0.5864(7) 0.0372(16) Uani 1 1 d . . . . .
C16 C 0.1690(6) 1.1767(6) -0.2570(12) 0.092(4) Uani 1 1 d . . . . .
H16 H 0.1539 1.2277 -0.3208 0.110 Uiso 1 1 calc R U . . .
C17 C 0.2217(5) 1.1159(7) -0.3003(10) 0.082(3) Uani 1 1 d . . . . .
H17 H 0.2415 1.1254 -0.3931 0.099 Uiso 1 1 calc R U . . .
C18 C 0.2451(4) 1.0399(5) -0.2034(8) 0.062(2) Uani 1 1 d . . . . .
H18 H 0.2797 0.9977 -0.2332 0.075 Uiso 1 1 calc R U . . .
C8 C 0.9599(4) 0.0756(5) 0.6631(8) 0.068(2) Uani 1 1 d . . . . .
H82 H 0.9547 0.0606 0.7691 0.103 Uiso 1 1 calc R U . . .
H83 H 0.9135 0.0885 0.6101 0.103 Uiso 1 1 calc R U . . .
H81 H 0.9899 0.1310 0.6581 0.103 Uiso 1 1 calc R U . . .
C24 C 0.3447(4) 1.1566(5) 0.1916(8) 0.055(2) Uani 1 1 d . . . . .
H24 H 0.3135 1.1752 0.2631 0.066 Uiso 1 1 calc R U . . .
C22 C 0.4371(5) 1.1982(7) 0.0292(11) 0.078(3) Uani 1 1 d . . . . .
H22 H 0.4677 1.2434 -0.0079 0.093 Uiso 1 1 calc R U . . .
C14 C 0.1630(4) 1.0859(5) -0.0254(8) 0.055(2) Uani 1 1 d . . . . .
H14 H 0.1421 1.0747 0.0656 0.066 Uiso 1 1 calc R U . . .
C7 C 0.9519(4) -0.1021(5) 0.6065(8) 0.062(2) Uani 1 1 d . . . . .
H71 H 0.9773 -0.1556 0.5683 0.094 Uiso 1 1 calc R U . . .
H72 H 0.9055 -0.0970 0.5499 0.094 Uiso 1 1 calc R U . . .
H73 H 0.9464 -0.1116 0.7139 0.094 Uiso 1 1 calc R U . . .
C15 C 0.1386(6) 1.1632(6) -0.1216(11) 0.088(3) Uani 1 1 d . . . . .
H15 H 0.1027 1.2039 -0.0936 0.105 Uiso 1 1 calc R U . . .
C26 C 0.3821(5) 0.9508(6) 0.4311(9) 0.059(2) Uani 1 1 d . . . . .
C23 C 0.3913(5) 1.2237(6) 0.1363(10) 0.068(2) Uani 1 1 d . . . . .
H23 H 0.3913 1.2864 0.1725 0.082 Uiso 1 1 calc R U . . .
C21 C 0.4373(4) 1.1043(6) -0.0228(9) 0.066(2) Uani 1 1 d . . . . .
H21 H 0.4684 1.0860 -0.0946 0.079 Uiso 1 1 calc R U . . .
H5 H 1.083(6) 0.024(7) 0.681(13) 0.14(5) Uiso 1 1 d . . . . .
H3 H 0.077(3) 0.908(5) -0.168(8) 0.06(2) Uiso 1 1 d . . . . .
H1 H 0.145(5) 0.728(9) 0.172(11) 0.22(6) Uiso 1 1 d D . . . .
H7 H 0.247(5) 0.816(7) 0.382(12) 0.16(4) 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
P1 O4 1.489(4) . ?
P1 O1 1.535(4) . ?
P1 O3 1.551(4) . ?
P1 O2 1.587(4) . ?
O2 C3 1.447(6) . ?
F1 C25 1.348(7) . ?
O6 C4 1.416(7) . ?
F5 C26 1.348(8) . ?
F3 C25 1.322(7) . ?
F6 C26 1.334(8) . ?
O5 C6 1.461(7) . ?
O7 C5 1.422(7) . ?
F2 C25 1.347(7) . ?
C5 C25 1.532(9) . ?
C5 C26 1.555(9) . ?
C5 C4 1.635(8) . ?
C13 C18 1.372(9) . ?
C13 C14 1.372(8) . ?
C13 C3 1.529(8) . ?
F4 C26 1.341(7) . ?
C3 C4 1.573(8) . ?
C4 C19 1.527(8) . ?
C19 C20 1.389(8) . ?
C19 C24 1.394(8) . ?
C20 C21 1.380(8) . ?
C6 C7 1.528(8) . ?
C6 C8 1.540(9) . ?
C6 C6 1.565(12) 3_756 ?
C16 C15 1.370(12) . ?
C16 C17 1.380(12) . ?
C17 C18 1.398(10) . ?
C24 C23 1.396(9) . ?
C22 C23 1.373(11) . ?
C22 C21 1.385(10) . ?
C14 C15 1.413(10) . ?

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 P1 O1 116.8(3) . . ?
O4 P1 O3 112.8(2) . . ?
O1 P1 O3 102.5(3) . . ?
O4 P1 O2 111.3(2) . . ?
O1 P1 O2 103.4(2) . . ?
O3 P1 O2 109.1(2) . . ?
C3 O2 P1 122.5(3) . . ?
O7 C5 C25 108.5(5) . . ?
O7 C5 C26 104.0(5) . . ?
C25 C5 C26 108.3(6) . . ?
O7 C5 C4 108.8(5) . . ?
C25 C5 C4 115.9(5) . . ?
C26 C5 C4 110.7(5) . . ?
C18 C13 C14 119.8(6) . . ?
C18 C13 C3 120.7(6) . . ?
C14 C13 C3 119.5(6) . . ?
O2 C3 C13 111.6(5) . . ?
O2 C3 C4 106.8(4) . . ?
C13 C3 C4 111.6(5) . . ?
O6 C4 C19 108.7(5) . . ?
O6 C4 C3 107.8(5) . . ?
C19 C4 C3 107.9(5) . . ?
O6 C4 C5 103.6(5) . . ?
C19 C4 C5 115.5(5) . . ?
C3 C4 C5 112.9(5) . . ?
F3 C25 F2 105.7(6) . . ?
F3 C25 F1 106.8(5) . . ?
F2 C25 F1 103.6(6) . . ?
F3 C25 C5 115.1(6) . . ?
F2 C25 C5 112.5(5) . . ?
F1 C25 C5 112.2(5) . . ?
C20 C19 C24 117.4(6) . . ?
C20 C19 C4 122.7(6) . . ?
C24 C19 C4 119.7(6) . . ?
C21 C20 C19 122.0(7) . . ?
O5 C6 C7 104.7(5) . . ?
O5 C6 C8 109.1(5) . . ?
C7 C6 C8 111.0(5) . . ?
O5 C6 C6 107.0(6) . 3_756 ?
C7 C6 C6 112.4(7) . 3_756 ?
C8 C6 C6 112.2(6) . 3_756 ?
C15 C16 C17 121.2(9) . . ?
C16 C17 C18 119.4(8) . . ?
C13 C18 C17 120.3(8) . . ?
C19 C24 C23 120.6(7) . . ?
C23 C22 C21 119.2(8) . . ?
C13 C14 C15 120.7(7) . . ?
C16 C15 C14 118.5(9) . . ?
F6 C26 F4 107.5(7) . . ?
F6 C26 F5 107.7(6) . . ?
F4 C26 F5 105.7(6) . . ?
F6 C26 C5 112.4(6) . . ?
F4 C26 C5 111.5(6) . . ?
F5 C26 C5 111.6(6) . . ?
C22 C23 C24 120.8(8) . . ?
C20 C21 C22 120.0(8) . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-2

_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

