# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_8a
_database_code_depnum_ccdc_archive 'CCDC 1568454'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2018-03-14 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         'C16 H21 F3 N O6 P'
_chemical_formula_sum            'C16 H21 F3 N O6 P'
_chemical_formula_weight         411.31

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'
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                   9.2602(5)
_cell_length_b                   9.4720(4)
_cell_length_c                   11.9414(4)
_cell_angle_alpha                107.154(4)
_cell_angle_beta                 96.395(3)
_cell_angle_gamma                95.550(4)
_cell_volume                     985.29(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    7906
_cell_measurement_theta_min      3.2615
_cell_measurement_theta_max      26.5487

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.93875
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_measurement_method       '/w scan'
_diffrn_reflns_number            17923
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.268
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3448
_reflns_number_gt                2844
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.1143P)²+0.5889P] 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         3447
_refine_ls_number_parameters     247
_refine_ls_number_restraints     113
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.2201
_refine_ls_wR_factor_gt          0.2121
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.154
_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 0.30056(10) 0.40468(9) 0.09981(7) 0.0603(3) Uani 1 1 d . . . . .
O2 O 0.3180(3) 0.5206(3) 0.0429(2) 0.0787(7) Uani 1 1 d . . . . .
O3 O 0.1724(3) 0.2764(3) 0.0394(2) 0.0759(7) Uani 1 1 d . . . . .
C4 C 0.0227(5) 0.3010(5) 0.0285(5) 0.1047(16) Uani 1 1 d D . . . .
H4B H 0.0155 0.3983 0.0189 0.126 Uiso 1 1 calc R U . . .
H4A H -0.0175 0.2980 0.0995 0.126 Uiso 1 1 calc R U . . .
C5 C -0.0626(5) 0.1811(6) -0.0778(4) 0.1118(17) Uani 1 1 d D . . . .
H5C H -0.0204 0.1827 -0.1473 0.168 Uiso 1 1 calc R U . . .
H5B H -0.1628 0.1989 -0.0875 0.168 Uiso 1 1 calc R U . . .
H5A H -0.0588 0.0854 -0.0660 0.168 Uiso 1 1 calc R U . . .
O6 O 0.2705(3) 0.4626(3) 0.2310(2) 0.0792(8) Uani 1 1 d . . . . .
C7 C 0.3374(9) 0.6096(7) 0.3050(5) 0.144(3) Uani 1 1 d D . . . .
H7B H 0.2742 0.6834 0.2980 0.173 Uiso 1 1 calc R U . . .
H7A H 0.4310 0.6359 0.2819 0.173 Uiso 1 1 calc R U . . .
C8 C 0.3587(13) 0.6032(12) 0.4305(5) 0.223(5) Uani 1 1 d D . . . .
H8C H 0.2656 0.5740 0.4512 0.335 Uiso 1 1 calc R U . . .
H8B H 0.4003 0.6998 0.4835 0.335 Uiso 1 1 calc R U . . .
H8A H 0.4236 0.5319 0.4366 0.335 Uiso 1 1 calc R U . . .
C9 C 0.4586(4) 0.3048(3) 0.0995(3) 0.0560(7) Uani 1 1 d . . . . .
H9 H 0.5407 0.3707 0.1552 0.067 Uiso 1 1 calc R U . . .
O10 O 0.4999(3) 0.2607(3) -0.0148(2) 0.0714(7) Uani 1 1 d . . . . .
H10 H 0.5498 0.3311 -0.0249 0.107 Uiso 1 1 calc R U . . .
C11 C 0.4286(4) 0.1651(3) 0.1339(3) 0.0570(8) Uani 1 1 d . . . . .
H11 H 0.3413 0.0972 0.0879 0.068 Uiso 1 1 calc R U . . .
N12 N 0.4538(3) 0.1735(3) 0.2594(2) 0.0625(7) Uani 1 1 d . U . . .
C13 C 0.5456(4) 0.0900(4) 0.1828(3) 0.0626(8) Uani 1 1 d . U . . .
H13 H 0.5210 -0.0184 0.1624 0.075 Uiso 1 1 calc R U . . .
C14 C 0.7056(5) 0.1434(5) 0.2079(4) 0.0797(10) Uani 1 1 d . U . . .
F15 F 0.7739(4) 0.0758(5) 0.1250(4) 0.1587(16) Uani 1 1 d . U . . .
F16 F 0.7656(4) 0.1159(5) 0.3038(4) 0.1497(15) Uani 1 1 d . U . . .
F17 F 0.7391(3) 0.2873(3) 0.2347(4) 0.1379(14) Uani 1 1 d . U . . .
C18 C 0.3602(4) 0.0919(4) 0.3106(3) 0.0711(9) Uani 1 1 d . U . . .
O19 O 0.3959(4) -0.0035(4) 0.3498(3) 0.1090(11) Uani 1 1 d . U . . .
O20 O 0.2345(3) 0.1418(3) 0.3096(3) 0.0841(8) Uani 1 1 d . U . . .
C21 C 0.1318(5) 0.0805(6) 0.3776(4) 0.0975(14) Uani 1 1 d . U . . .
H21B H 0.1519 -0.0185 0.3763 0.117 Uiso 1 1 calc R U . . .
H21A H 0.0316 0.0720 0.3398 0.117 Uiso 1 1 calc R U . . .
C22 C 0.1477(5) 0.1795(5) 0.5044(4) 0.0783(10) Uani 1 1 d . U . . .
C23 C 0.2419(6) 0.1598(6) 0.5916(5) 0.1023(14) Uani 1 1 d . U . . .
H23 H 0.2989 0.0826 0.5741 0.123 Uiso 1 1 calc R U . . .
C24 C 0.2547(7) 0.2550(7) 0.7085(5) 0.1114(16) Uani 1 1 d . U . . .
H24 H 0.3185 0.2397 0.7683 0.134 Uiso 1 1 calc R U . . .
C25 C 0.1742(7) 0.3681(6) 0.7334(4) 0.1002(14) Uani 1 1 d . U . . .
H25 H 0.1849 0.4336 0.8100 0.120 Uiso 1 1 calc R U . . .
C26 C 0.0795(7) 0.3861(7) 0.6483(5) 0.1165(17) Uani 1 1 d . U . . .
H26 H 0.0210 0.4619 0.6667 0.140 Uiso 1 1 calc R U . . .
C27 C 0.0667(6) 0.2945(6) 0.5339(5) 0.1036(15) Uani 1 1 d . U . . .
H27 H 0.0017 0.3110 0.4753 0.124 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.458(3) . ?
P1 O3 1.555(3) . ?
P1 O6 1.566(3) . ?
P1 C9 1.817(3) . ?
O3 C4 1.426(5) . ?
C4 C5 1.509(4) . ?
C4 H4B 0.9700 . ?
C4 H4A 0.9700 . ?
C5 H5C 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5A 0.9600 . ?
O6 C7 1.445(6) . ?
C7 C8 1.509(5) . ?
C7 H7B 0.9700 . ?
C7 H7A 0.9700 . ?
C8 H8C 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8A 0.9600 . ?
C9 O10 1.412(4) . ?
C9 C11 1.508(4) . ?
C9 H9 0.9800 . ?
O10 H10 0.8200 . ?
C11 N12 1.468(4) . ?
C11 C13 1.508(5) . ?
C11 H11 0.9800 . ?
N12 C18 1.411(5) . ?
N12 C13 1.436(4) . ?
C13 C14 1.486(5) . ?
C13 H13 0.9800 . ?
C14 F15 1.278(5) . ?
C14 F17 1.302(5) . ?
C14 F16 1.323(5) . ?
C18 O19 1.190(5) . ?
C18 O20 1.298(5) . ?
O20 C21 1.497(5) . ?
C21 C22 1.510(6) . ?
C21 H21B 0.9700 . ?
C21 H21A 0.9700 . ?
C22 C23 1.350(7) . ?
C22 C27 1.366(7) . ?
C23 C24 1.405(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.344(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.328(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.371(7) . ?
C26 H26 0.9300 . ?
C27 H27 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 115.55(16) . . ?
O2 P1 O6 114.13(15) . . ?
O3 P1 O6 103.64(15) . . ?
O2 P1 C9 112.59(15) . . ?
O3 P1 C9 102.38(14) . . ?
O6 P1 C9 107.44(15) . . ?
C4 O3 P1 122.6(2) . . ?
O3 C4 C5 108.9(4) . . ?
O3 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
O3 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
H4B C4 H4A 108.3 . . ?
C4 C5 H5C 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5C C5 H5B 109.5 . . ?
C4 C5 H5A 109.5 . . ?
H5C C5 H5A 109.5 . . ?
H5B C5 H5A 109.5 . . ?
C7 O6 P1 119.5(3) . . ?
O6 C7 C8 106.4(5) . . ?
O6 C7 H7B 110.4 . . ?
C8 C7 H7B 110.4 . . ?
O6 C7 H7A 110.4 . . ?
C8 C7 H7A 110.4 . . ?
H7B C7 H7A 108.6 . . ?
C7 C8 H8C 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8C C8 H8B 109.5 . . ?
C7 C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
H8B C8 H8A 109.5 . . ?
O10 C9 C11 106.9(2) . . ?
O10 C9 P1 110.4(2) . . ?
C11 C9 P1 112.6(2) . . ?
O10 C9 H9 109.0 . . ?
C11 C9 H9 109.0 . . ?
P1 C9 H9 109.0 . . ?
C9 O10 H10 109.5 . . ?
N12 C11 C13 57.7(2) . . ?
N12 C11 C9 119.5(2) . . ?
C13 C11 C9 124.3(3) . . ?
N12 C11 H11 114.5 . . ?
C13 C11 H11 114.5 . . ?
C9 C11 H11 114.5 . . ?
C18 N12 C13 116.4(3) . . ?
C18 N12 C11 123.1(3) . . ?
C13 N12 C11 62.5(2) . . ?
N12 C13 C14 117.5(3) . . ?
N12 C13 C11 59.8(2) . . ?
C14 C13 C11 125.9(3) . . ?
N12 C13 H13 114.1 . . ?
C14 C13 H13 114.1 . . ?
C11 C13 H13 114.1 . . ?
F15 C14 F17 110.7(4) . . ?
F15 C14 F16 105.3(4) . . ?
F17 C14 F16 102.6(4) . . ?
F15 C14 C13 112.4(4) . . ?
F17 C14 C13 114.5(4) . . ?
F16 C14 C13 110.6(4) . . ?
O19 C18 O20 127.6(4) . . ?
O19 C18 N12 124.0(4) . . ?
O20 C18 N12 108.4(3) . . ?
C18 O20 C21 114.0(4) . . ?
O20 C21 C22 111.3(4) . . ?
O20 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
O20 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
H21B C21 H21A 108.0 . . ?
C23 C22 C27 117.8(4) . . ?
C23 C22 C21 122.2(5) . . ?
C27 C22 C21 120.1(4) . . ?
C22 C23 C24 120.6(5) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 119.8(5) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C26 C25 C24 119.9(5) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 120.8(6) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C22 C27 C26 121.2(5) . . ?
C22 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 P1 O3 C4 -62.4(4) . . . . ?
O6 P1 O3 C4 63.2(4) . . . . ?
C9 P1 O3 C4 174.8(4) . . . . ?
P1 O3 C4 C5 153.4(4) . . . . ?
O2 P1 O6 C7 -33.9(5) . . . . ?
O3 P1 O6 C7 -160.4(4) . . . . ?
C9 P1 O6 C7 91.7(4) . . . . ?
P1 O6 C7 C8 -150.4(6) . . . . ?
O2 P1 C9 O10 -48.3(3) . . . . ?
O3 P1 C9 O10 76.4(2) . . . . ?
O6 P1 C9 O10 -174.8(2) . . . . ?
O2 P1 C9 C11 -167.7(2) . . . . ?
O3 P1 C9 C11 -43.0(2) . . . . ?
O6 P1 C9 C11 65.8(2) . . . . ?
O10 C9 C11 N12 150.1(3) . . . . ?
P1 C9 C11 N12 -88.4(3) . . . . ?
O10 C9 C11 C13 81.1(3) . . . . ?
P1 C9 C11 C13 -157.5(2) . . . . ?
C13 C11 N12 C18 -105.0(4) . . . . ?
C9 C11 N12 C18 140.9(3) . . . . ?
C9 C11 N12 C13 -114.1(3) . . . . ?
C18 N12 C13 C14 -127.0(3) . . . . ?
C11 N12 C13 C14 117.5(3) . . . . ?
C18 N12 C13 C11 115.5(3) . . . . ?
C9 C11 C13 N12 105.9(3) . . . . ?
N12 C11 C13 C14 -103.8(4) . . . . ?
C9 C11 C13 C14 2.0(5) . . . . ?
N12 C13 C14 F15 -170.0(4) . . . . ?
C11 C13 C14 F15 -98.9(5) . . . . ?
N12 C13 C14 F17 -42.6(5) . . . . ?
C11 C13 C14 F17 28.5(6) . . . . ?
N12 C13 C14 F16 72.7(5) . . . . ?
C11 C13 C14 F16 143.8(4) . . . . ?
C13 N12 C18 O19 41.8(5) . . . . ?
C11 N12 C18 O19 114.9(5) . . . . ?
C13 N12 C18 O20 -139.8(3) . . . . ?
C11 N12 C18 O20 -66.7(4) . . . . ?
O19 C18 O20 C21 6.9(6) . . . . ?
N12 C18 O20 C21 -171.4(3) . . . . ?
C18 O20 C21 C22 91.7(5) . . . . ?
O20 C21 C22 C23 -90.6(5) . . . . ?
O20 C21 C22 C27 88.5(5) . . . . ?
C27 C22 C23 C24 0.3(7) . . . . ?
C21 C22 C23 C24 179.4(4) . . . . ?
C22 C23 C24 C25 -1.1(8) . . . . ?
C23 C24 C25 C26 2.4(9) . . . . ?
C24 C25 C26 C27 -2.8(9) . . . . ?
C23 C22 C27 C26 -0.6(8) . . . . ?
C21 C22 C27 C26 -179.8(5) . . . . ?
C25 C26 C27 C22 1.9(9) . . . . ?

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
C9 H9 F17 0.98 2.29 2.948(4) 123.7 .
O10 H10 O2 0.82 1.85 2.665(4) 173.0 2_665
C13 H13 O10 0.98 2.42 3.294(4) 148.0 2_655

_refine_diff_density_max         0.675
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_13d
_database_code_depnum_ccdc_archive 'CCDC 1569663'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-14 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         'C27 H34 N O4 P'
_chemical_formula_sum            'C27 H34 N O4 P'
_chemical_formula_weight         467.52

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      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

_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+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   18.3893(4)
_cell_length_b                   18.3893(4)
_cell_length_c                   15.9702(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5400.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4321
_cell_measurement_theta_min      3.4930
_cell_measurement_theta_max      25.5980

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_F_000             2000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.79673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_reflns_number            14476
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.379
_diffrn_reflns_theta_max         26.495
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5216
_reflns_number_gt                4155
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_max     0.906
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2015)'

_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)+(0.0570P)²+0.5031P] 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_abs_structure_details 
;
 Flack x determined using 1428 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         5216
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.47732(4) 0.84282(4) 0.43911(5) 0.0525(2) Uani 1 1 d . . . . .
O2 O 0.45235(13) 0.88141(13) 0.36427(13) 0.0691(6) Uani 1 1 d . . . . .
O3 O 0.45269(13) 0.76089(12) 0.44132(16) 0.0720(6) Uani 1 1 d . . . . .
C4 C 0.3919(3) 0.7327(3) 0.3974(3) 0.1055(15) Uani 1 1 d . . . . .
H4A H 0.3820 0.7629 0.3489 0.127 Uiso 1 1 calc R U . . .
H4B H 0.3494 0.7339 0.4335 0.127 Uiso 1 1 calc R U . . .
C5 C 0.4056(3) 0.6575(3) 0.3703(4) 0.145(2) Uani 1 1 d . . . . .
H5A H 0.4458 0.6567 0.3319 0.218 Uiso 1 1 calc R U . . .
H5B H 0.3630 0.6386 0.3430 0.218 Uiso 1 1 calc R U . . .
H5C H 0.4169 0.6280 0.4181 0.218 Uiso 1 1 calc R U . . .
O6 O 0.56190(12) 0.83688(15) 0.44994(14) 0.0743(7) Uani 1 1 d . . . . .
C7 C 0.6092(2) 0.8174(3) 0.3833(3) 0.0965(14) Uani 1 1 d . . . . .
H7A H 0.6114 0.8565 0.3427 0.116 Uiso 1 1 calc R U . . .
H7B H 0.5909 0.7743 0.3554 0.116 Uiso 1 1 calc R U . . .
C8 C 0.6824(2) 0.8031(3) 0.4172(3) 0.1066(16) Uani 1 1 d . . . . .
H8A H 0.7139 0.7874 0.3728 0.160 Uiso 1 1 calc R U . . .
H8B H 0.6795 0.7658 0.4591 0.160 Uiso 1 1 calc R U . . .
H8C H 0.7014 0.8468 0.4417 0.160 Uiso 1 1 calc R U . . .
C9 C 0.45053(16) 0.88064(16) 0.53960(18) 0.0504(7) Uani 1 1 d . . . . .
H9 H 0.4714 0.8502 0.5839 0.060 Uiso 1 1 calc R U . . .
O10 O 0.47987(12) 0.95188(11) 0.54770(15) 0.0630(6) Uani 1 1 d . . . . .
H10 H 0.5215 0.9493 0.5660 0.095 Uiso 1 1 calc R U . . .
C11 C 0.36734(15) 0.88209(15) 0.55107(17) 0.0456(6) Uani 1 1 d . . . . .
H11 H 0.3488 0.8379 0.5243 0.055 Uiso 1 1 calc R U . . .
N12 N 0.34206(13) 0.87955(12) 0.63881(14) 0.0461(5) Uani 1 1 d . . . . .
C13 C 0.35533(17) 0.80877(15) 0.67898(18) 0.0508(7) Uani 1 1 d . . . . .
H13A H 0.3388 0.8111 0.7366 0.061 Uiso 1 1 calc R U . . .
H13B H 0.4073 0.7996 0.6798 0.061 Uiso 1 1 calc R U . . .
C14 C 0.31808(17) 0.74621(16) 0.63619(18) 0.0525(7) Uani 1 1 d . . . . .
C15 C 0.3556(2) 0.68274(18) 0.6197(3) 0.0770(10) Uani 1 1 d . . . . .
H15 H 0.4041 0.6787 0.6356 0.092 Uiso 1 1 calc R U . . .
C16 C 0.3219(3) 0.6252(2) 0.5798(3) 0.1047(15) Uani 1 1 d . . . . .
H16 H 0.3479 0.5830 0.5684 0.126 Uiso 1 1 calc R U . . .
C17 C 0.2500(3) 0.6301(3) 0.5567(3) 0.1016(15) Uani 1 1 d . . . . .
H17 H 0.2270 0.5912 0.5305 0.122 Uiso 1 1 calc R U . . .
C18 C 0.2129(2) 0.6927(3) 0.5728(3) 0.0905(13) Uani 1 1 d . . . . .
H18 H 0.1643 0.6965 0.5571 0.109 Uiso 1 1 calc R U . . .
C19 C 0.2466(2) 0.75050(19) 0.6120(2) 0.0679(9) Uani 1 1 d . . . . .
H19 H 0.2205 0.7929 0.6222 0.081 Uiso 1 1 calc R U . . .
C20 C 0.36927(18) 0.93846(17) 0.6922(2) 0.0548(7) Uani 1 1 d . . . . .
H20A H 0.3703 0.9832 0.6601 0.066 Uiso 1 1 calc R U . . .
H20B H 0.4188 0.9274 0.7089 0.066 Uiso 1 1 calc R U . . .
C21 C 0.32357(18) 0.95002(16) 0.76996(19) 0.0570(8) Uani 1 1 d . . . . .
C22 C 0.2492(2) 0.9369(2) 0.7704(2) 0.0721(9) Uani 1 1 d . . . . .
H22 H 0.2269 0.9181 0.7229 0.087 Uiso 1 1 calc R U . . .
C23 C 0.2081(3) 0.9516(3) 0.8411(3) 0.0941(14) Uani 1 1 d . . . . .
H23 H 0.1584 0.9425 0.8413 0.113 Uiso 1 1 calc R U . . .
C24 C 0.2420(4) 0.9802(3) 0.9120(3) 0.1082(17) Uani 1 1 d . . . . .
H24 H 0.2145 0.9911 0.9593 0.130 Uiso 1 1 calc R U . . .
C25 C 0.3150(3) 0.9922(2) 0.9122(3) 0.0973(14) Uani 1 1 d . . . . .
H25 H 0.3376 1.0104 0.9599 0.117 Uiso 1 1 calc R U . . .
C26 C 0.3553(2) 0.9774(2) 0.8418(2) 0.0741(10) Uani 1 1 d . . . . .
H26 H 0.4051 0.9861 0.8425 0.089 Uiso 1 1 calc R U . . .
C27 C 0.33360(16) 0.94606(17) 0.5032(2) 0.0555(7) Uani 1 1 d . . . . .
H27A H 0.3403 0.9899 0.5362 0.067 Uiso 1 1 calc R U . . .
H27B H 0.3602 0.9524 0.4513 0.067 Uiso 1 1 calc R U . . .
C28 C 0.25477(17) 0.93886(17) 0.4830(2) 0.0569(8) Uani 1 1 d . . . . .
C29 C 0.2340(3) 0.9079(3) 0.4085(3) 0.1205(19) Uani 1 1 d . . . . .
H29 H 0.2688 0.8901 0.3714 0.145 Uiso 1 1 calc R U . . .
C30 C 0.1595(5) 0.9034(4) 0.3890(6) 0.195(4) Uani 1 1 d . . . . .
H30 H 0.1445 0.8819 0.3392 0.234 Uiso 1 1 calc R U . . .
C31 C 0.1077(4) 0.9317(4) 0.4454(8) 0.177(4) Uani 1 1 d . . . . .
H31 H 0.0583 0.9284 0.4333 0.212 Uiso 1 1 calc R U . . .
C32 C 0.1296(3) 0.9626(4) 0.5149(5) 0.142(3) Uani 1 1 d . . . . .
H32 H 0.0955 0.9818 0.5518 0.171 Uiso 1 1 calc R U . . .
C33 C 0.2024(2) 0.9668(3) 0.5338(3) 0.0969(14) Uani 1 1 d . . . . .
H33 H 0.2163 0.9897 0.5832 0.116 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 O2 1.464(2) . ?
P1 O6 1.569(2) . ?
P1 O3 1.574(3) . ?
P1 C9 1.817(3) . ?
O3 C4 1.418(5) . ?
C4 C5 1.472(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
O6 C7 1.420(4) . ?
C7 C8 1.475(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O10 1.423(4) . ?
C9 C11 1.541(4) . ?
C9 H9 0.9800 . ?
O10 H10 0.8200 . ?
C11 N12 1.477(3) . ?
C11 C27 1.534(4) . ?
C11 H11 0.9800 . ?
N12 C20 1.467(4) . ?
N12 C13 1.471(3) . ?
C13 C14 1.503(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.372(5) . ?
C14 C15 1.381(5) . ?
C15 C16 1.383(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.362(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.514(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C26 1.382(5) . ?
C21 C22 1.388(5) . ?
C22 C23 1.385(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.395(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.361(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.374(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.491(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C33 1.361(5) . ?
C28 C29 1.373(5) . ?
C29 C30 1.409(9) . ?
C29 H29 0.9300 . ?
C30 C31 1.410(12) . ?
C30 H30 0.9300 . ?
C31 C32 1.311(11) . ?
C31 H31 0.9300 . ?
C32 C33 1.374(7) . ?
C32 H32 0.9300 . ?
C33 H33 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 O6 115.78(14) . . ?
O2 P1 O3 113.09(15) . . ?
O6 P1 O3 102.49(14) . . ?
O2 P1 C9 116.77(13) . . ?
O6 P1 C9 101.43(13) . . ?
O3 P1 C9 105.58(14) . . ?
C4 O3 P1 124.5(3) . . ?
O3 C4 C5 110.7(5) . . ?
O3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 O6 P1 122.8(2) . . ?
O6 C7 C8 109.2(4) . . ?
O6 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
O6 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O10 C9 C11 110.5(2) . . ?
O10 C9 P1 109.3(2) . . ?
C11 C9 P1 112.4(2) . . ?
O10 C9 H9 108.2 . . ?
C11 C9 H9 108.2 . . ?
P1 C9 H9 108.2 . . ?
C9 O10 H10 109.5 . . ?
N12 C11 C27 111.7(2) . . ?
N12 C11 C9 115.1(2) . . ?
C27 C11 C9 110.8(2) . . ?
N12 C11 H11 106.2 . . ?
C27 C11 H11 106.2 . . ?
C9 C11 H11 106.2 . . ?
C20 N12 C13 110.1(2) . . ?
C20 N12 C11 114.9(2) . . ?
C13 N12 C11 112.9(2) . . ?
N12 C13 C14 113.8(2) . . ?
N12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C19 C14 C15 118.3(3) . . ?
C19 C14 C13 121.4(3) . . ?
C15 C14 C13 120.4(3) . . ?
C14 C15 C16 120.7(4) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.2(4) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 120.7(4) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 120.9(4) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
N12 C20 C21 113.0(3) . . ?
N12 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
N12 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C26 C21 C22 118.3(3) . . ?
C26 C21 C20 119.8(3) . . ?
C22 C21 C20 121.8(3) . . ?
C23 C22 C21 120.5(4) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.5(5) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 120.2(4) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.9(4) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C21 121.6(4) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?
C28 C27 C11 115.7(2) . . ?
C28 C27 H27A 108.4 . . ?
C11 C27 H27A 108.4 . . ?
C28 C27 H27B 108.4 . . ?
C11 C27 H27B 108.4 . . ?
H27A C27 H27B 107.4 . . ?
C33 C28 C29 118.5(4) . . ?
C33 C28 C27 121.7(3) . . ?
C29 C28 C27 119.6(4) . . ?
C28 C29 C30 119.1(6) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C29 C30 C31 119.7(7) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C32 C31 C30 119.5(6) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C31 C32 C33 120.7(7) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C28 C33 C32 122.4(5) . . ?
C28 C33 H33 118.8 . . ?
C32 C33 H33 118.8 . . ?

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 O3 C4 -23.5(4) . . . . ?
O6 P1 O3 C4 -148.8(3) . . . . ?
C9 P1 O3 C4 105.4(3) . . . . ?
P1 O3 C4 C5 146.6(4) . . . . ?
O2 P1 O6 C7 -45.2(4) . . . . ?
O3 P1 O6 C7 78.3(3) . . . . ?
C9 P1 O6 C7 -172.7(3) . . . . ?
P1 O6 C7 C8 -169.3(3) . . . . ?
O2 P1 C9 O10 -61.5(2) . . . . ?
O6 P1 C9 O10 65.3(2) . . . . ?
O3 P1 C9 O10 171.84(19) . . . . ?
O2 P1 C9 C11 61.5(2) . . . . ?
O6 P1 C9 C11 -171.8(2) . . . . ?
O3 P1 C9 C11 -65.2(2) . . . . ?
O10 C9 C11 N12 -84.2(3) . . . . ?
P1 C9 C11 N12 153.5(2) . . . . ?
O10 C9 C11 C27 43.8(3) . . . . ?
P1 C9 C11 C27 -78.5(3) . . . . ?
C27 C11 N12 C20 -69.6(3) . . . . ?
C9 C11 N12 C20 58.0(3) . . . . ?
C27 C11 N12 C13 163.1(2) . . . . ?
C9 C11 N12 C13 -69.4(3) . . . . ?
C20 N12 C13 C14 170.1(3) . . . . ?
C11 N12 C13 C14 -60.1(3) . . . . ?
N12 C13 C14 C19 -46.1(4) . . . . ?
N12 C13 C14 C15 133.5(3) . . . . ?
C19 C14 C15 C16 0.1(5) . . . . ?
C13 C14 C15 C16 -179.5(3) . . . . ?
C14 C15 C16 C17 -0.8(7) . . . . ?
C15 C16 C17 C18 0.9(8) . . . . ?
C16 C17 C18 C19 -0.3(7) . . . . ?
C15 C14 C19 C18 0.5(5) . . . . ?
C13 C14 C19 C18 -180.0(3) . . . . ?
C17 C18 C19 C14 -0.4(6) . . . . ?
C13 N12 C20 C21 -71.4(3) . . . . ?
C11 N12 C20 C21 159.8(2) . . . . ?
N12 C20 C21 C26 151.5(3) . . . . ?
N12 C20 C21 C22 -31.5(4) . . . . ?
C26 C21 C22 C23 0.5(5) . . . . ?
C20 C21 C22 C23 -176.6(3) . . . . ?
C21 C22 C23 C24 0.4(6) . . . . ?
C22 C23 C24 C25 -1.3(7) . . . . ?
C23 C24 C25 C26 1.2(8) . . . . ?
C24 C25 C26 C21 -0.3(7) . . . . ?
C22 C21 C26 C25 -0.5(5) . . . . ?
C20 C21 C26 C25 176.6(3) . . . . ?
N12 C11 C27 C28 -71.7(3) . . . . ?
C9 C11 C27 C28 158.5(3) . . . . ?
C11 C27 C28 C33 93.8(4) . . . . ?
C11 C27 C28 C29 -90.9(4) . . . . ?
C33 C28 C29 C30 -2.6(8) . . . . ?
C27 C28 C29 C30 -178.1(5) . . . . ?
C28 C29 C30 C31 1.0(11) . . . . ?
C29 C30 C31 C32 0.8(13) . . . . ?
C30 C31 C32 C33 -0.9(12) . . . . ?
C29 C28 C33 C32 2.7(7) . . . . ?
C27 C28 C33 C32 178.0(4) . . . . ?
C31 C32 C33 C28 -0.9(10) . . . . ?

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
O10 H10 O2 0.82 1.95 2.764(3) 174.5 3_655

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.029

####################################################################### 
# 
# 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_36
_database_code_depnum_ccdc_archive 'CCDC 1568457'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2018-03-14 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         'C22 H37 N2 O8 P S'
_chemical_formula_sum            'C22 H37 N2 O8 P S'
_chemical_formula_weight         520.56

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.2960(6)
_cell_length_b                   12.0965(6)
_cell_length_c                   12.4628(6)
_cell_angle_alpha                112.998(5)
_cell_angle_beta                 110.653(4)
_cell_angle_gamma                98.152(4)
_cell_volume                     1387.41(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    7252
_cell_measurement_theta_min      3.3611
_cell_measurement_theta_max      26.3749

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.219
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.97376
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_measurement_method       '/w scan'
_diffrn_reflns_number            16691
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.368
_diffrn_reflns_theta_max         26.432
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5328
_reflns_number_gt                4503
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.0997P)²+0.6039P] 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         5328
_refine_ls_number_parameters     315
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1809
_refine_ls_wR_factor_gt          0.1717
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.60295(7) 0.39950(6) 0.19617(7) 0.0586(2) Uani 1 1 d . . . . .
O2 O 0.5974(2) 0.3541(2) 0.0670(2) 0.0785(6) Uani 1 1 d . . . . .
O3 O 0.4883(2) 0.4505(2) 0.2139(2) 0.0794(6) Uani 1 1 d . . . . .
C4 C 0.4268(5) 0.5167(4) 0.1440(5) 0.1166(15) Uani 1 1 d D . . . .
H4A H 0.4902 0.5555 0.1226 0.140 Uiso 1 1 calc R U . . .
H4B H 0.4049 0.5837 0.1999 0.140 Uiso 1 1 calc R U . . .
C5 C 0.3012(5) 0.4261(7) 0.0201(6) 0.176(3) Uani 1 1 d D . . . .
H5A H 0.3218 0.3570 -0.0329 0.264 Uiso 1 1 calc R U . . .
H5B H 0.2669 0.4701 -0.0270 0.264 Uiso 1 1 calc R U . . .
H5C H 0.2353 0.3937 0.0417 0.264 Uiso 1 1 calc R U . . .
O6 O 0.7394(2) 0.5065(2) 0.2972(3) 0.0918(7) Uani 1 1 d . . . . .
C7 C 0.7651(6) 0.5775(5) 0.4228(5) 0.148(2) Uani 1 1 d D . . . .
H7A H 0.7702 0.5244 0.4648 0.177 Uiso 1 1 calc R U . . .
H7B H 0.6923 0.6107 0.4254 0.177 Uiso 1 1 calc R U . . .
C8 C 0.8948(7) 0.6865(7) 0.4966(6) 0.201(4) Uani 1 1 d D . . . .
H8A H 0.9657 0.6543 0.4881 0.302 Uiso 1 1 calc R U . . .
H8B H 0.9148 0.7299 0.5870 0.302 Uiso 1 1 calc R U . . .
H8C H 0.8862 0.7445 0.4615 0.302 Uiso 1 1 calc R U . . .
C9 C 0.5945(2) 0.2804(2) 0.2506(2) 0.0488(5) Uani 1 1 d . . . . .
H9 H 0.6043 0.3229 0.3397 0.059 Uiso 1 1 calc R U . . .
N10 N 0.46476(19) 0.18109(18) 0.17082(19) 0.0515(5) Uani 1 1 d . . . . .
H10 H 0.4404 0.1373 0.0887 0.062 Uiso 1 1 calc R U . . .
S11 S 0.36451(6) 0.14866(6) 0.22723(6) 0.0565(2) Uani 1 1 d . . . . .
O12 O 0.4382(2) 0.2062(2) 0.3645(2) 0.0803(6) Uani 1 1 d . . . . .
O13 O 0.29663(19) 0.01436(18) 0.1512(2) 0.0693(5) Uani 1 1 d . . . . .
C14 C 0.2410(2) 0.2204(2) 0.1921(2) 0.0553(6) Uani 1 1 d . . . . .
C15 C 0.1244(3) 0.1528(3) 0.0771(3) 0.0623(6) Uani 1 1 d . . . . .
H15 H 0.1126 0.0709 0.0180 0.075 Uiso 1 1 calc R U . . .
C16 C 0.0253(3) 0.2067(3) 0.0495(3) 0.0729(8) Uani 1 1 d . . . . .
H16 H -0.0531 0.1599 -0.0281 0.087 Uiso 1 1 calc R U . . .
C17 C 0.0400(3) 0.3275(3) 0.1339(4) 0.0747(8) Uani 1 1 d . . . . .
C18 C 0.1572(4) 0.3945(3) 0.2483(4) 0.0868(10) Uani 1 1 d . . . . .
H18 H 0.1689 0.4767 0.3065 0.104 Uiso 1 1 calc R U . . .
C19 C 0.2579(3) 0.3427(3) 0.2789(3) 0.0751(8) Uani 1 1 d . . . . .
H19 H 0.3360 0.3894 0.3567 0.090 Uiso 1 1 calc R U . . .
C20 C -0.0682(4) 0.3858(4) 0.1016(5) 0.1119(14) Uani 1 1 d . . . . .
H20A H -0.0411 0.4470 0.0766 0.168 Uiso 1 1 calc R U . . .
H20B H -0.0830 0.4270 0.1767 0.168 Uiso 1 1 calc R U . . .
H20C H -0.1494 0.3206 0.0309 0.168 Uiso 1 1 calc R U . . .
C21 C 0.7116(2) 0.2271(2) 0.2561(2) 0.0501(5) Uani 1 1 d . . . . .
H21 H 0.7959 0.2977 0.3042 0.060 Uiso 1 1 calc R U . . .
N22 N 0.7189(2) 0.14655(18) 0.31797(18) 0.0522(5) Uani 1 1 d . . . . .
C23 C 0.6945(3) 0.0134(2) 0.2269(2) 0.0552(6) Uani 1 1 d . . . . .
O24 O 0.64199(17) 0.01370(15) 0.10448(16) 0.0567(4) Uani 1 1 d . . . . .
C25 C 0.7001(3) 0.1369(2) 0.1247(2) 0.0551(6) Uani 1 1 d . . . . .
H25A H 0.6434 0.1523 0.0566 0.066 Uiso 1 1 calc R U . . .
H25B H 0.7875 0.1464 0.1262 0.066 Uiso 1 1 calc R U . . .
C26 C 0.5885(3) -0.0823(3) 0.2217(3) 0.0708(7) Uani 1 1 d . . . . .
H26A H 0.5125 -0.0538 0.2164 0.106 Uiso 1 1 calc R U . . .
H26B H 0.6237 -0.0912 0.2991 0.106 Uiso 1 1 calc R U . . .
H26C H 0.5618 -0.1628 0.1465 0.106 Uiso 1 1 calc R U . . .
C27 C 0.8246(3) -0.0175(3) 0.2505(3) 0.0779(8) Uani 1 1 d . . . . .
H27A H 0.8073 -0.1004 0.1828 0.117 Uiso 1 1 calc R U . . .
H27B H 0.8608 -0.0161 0.3334 0.117 Uiso 1 1 calc R U . . .
H27C H 0.8877 0.0444 0.2502 0.117 Uiso 1 1 calc R U . . .
C28 C 0.7627(3) 0.1996(2) 0.4486(2) 0.0583(6) Uani 1 1 d . . . . .
O29 O 0.7890(2) 0.31229(18) 0.51752(18) 0.0744(6) Uani 1 1 d . . . . .
O30 O 0.7746(2) 0.11289(19) 0.48869(17) 0.0702(5) Uani 1 1 d . . . . .
C31 C 0.8023(4) 0.1405(3) 0.6226(3) 0.0806(9) Uani 1 1 d . . . . .
C32 C 0.9400(5) 0.2357(5) 0.7148(4) 0.1207(16) Uani 1 1 d . . . . .
H32A H 1.0019 0.2104 0.6816 0.181 Uiso 1 1 calc R U . . .
H32B H 0.9670 0.2397 0.7988 0.181 Uiso 1 1 calc R U . . .
H32C H 0.9389 0.3178 0.7229 0.181 Uiso 1 1 calc R U . . .
C33 C 0.8014(5) 0.0141(4) 0.6176(4) 0.1060(13) Uani 1 1 d . . . . .
H33A H 0.7126 -0.0456 0.5617 0.159 Uiso 1 1 calc R U . . .
H33B H 0.8295 0.0234 0.7037 0.159 Uiso 1 1 calc R U . . .
H33C H 0.8615 -0.0161 0.5840 0.159 Uiso 1 1 calc R U . . .
C34 C 0.6939(6) 0.1836(7) 0.6515(6) 0.146(2) Uani 1 1 d . . . . .
H34A H 0.6994 0.2648 0.6547 0.219 Uiso 1 1 calc R U . . .
H34B H 0.7045 0.1905 0.7340 0.219 Uiso 1 1 calc R U . . .
H34C H 0.6083 0.1230 0.5843 0.219 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 O2 1.457(2) . ?
P1 O3 1.558(2) . ?
P1 O6 1.558(2) . ?
P1 C9 1.821(2) . ?
O3 C4 1.470(4) . ?
C4 C5 1.513(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
O6 C7 1.353(5) . ?
C7 C8 1.512(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N10 1.455(3) . ?
C9 C21 1.543(3) . ?
C9 H9 0.9800 . ?
N10 S11 1.607(2) . ?
N10 H10 0.8600 . ?
S11 O12 1.416(2) . ?
S11 O13 1.434(2) . ?
S11 C14 1.761(3) . ?
C14 C15 1.381(4) . ?
C14 C19 1.385(4) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(5) . ?
C17 C20 1.508(5) . ?
C18 C19 1.384(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N22 1.455(3) . ?
C21 C25 1.517(3) . ?
C21 H21 0.9800 . ?
N22 C28 1.354(3) . ?
N22 C23 1.478(3) . ?
C23 O24 1.430(3) . ?
C23 C26 1.508(4) . ?
C23 C27 1.524(4) . ?
O24 C25 1.424(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 O29 1.214(3) . ?
C28 O30 1.331(3) . ?
O30 C31 1.471(3) . ?
C31 C34 1.498(6) . ?
C31 C33 1.504(5) . ?
C31 C32 1.504(5) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 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 116.21(13) . . ?
O2 P1 O6 108.38(15) . . ?
O3 P1 O6 108.66(14) . . ?
O2 P1 C9 114.85(11) . . ?
O3 P1 C9 102.05(11) . . ?
O6 P1 C9 106.07(13) . . ?
C4 O3 P1 121.8(2) . . ?
O3 C4 C5 111.1(4) . . ?
O3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
O3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 O6 P1 121.3(3) . . ?
O6 C7 C8 111.4(5) . . ?
O6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
O6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N10 C9 C21 112.55(18) . . ?
N10 C9 P1 111.14(16) . . ?
C21 C9 P1 110.94(16) . . ?
N10 C9 H9 107.3 . . ?
C21 C9 H9 107.3 . . ?
P1 C9 H9 107.3 . . ?
C9 N10 S11 123.80(16) . . ?
C9 N10 H10 118.1 . . ?
S11 N10 H10 118.1 . . ?
O12 S11 O13 120.74(14) . . ?
O12 S11 N10 107.73(12) . . ?
O13 S11 N10 106.35(11) . . ?
O12 S11 C14 107.79(13) . . ?
O13 S11 C14 105.95(12) . . ?
N10 S11 C14 107.69(11) . . ?
C15 C14 C19 119.5(3) . . ?
C15 C14 S11 119.39(19) . . ?
C19 C14 S11 121.1(2) . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 121.4(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 118.0(3) . . ?
C16 C17 C20 120.8(3) . . ?
C18 C17 C20 121.1(3) . . ?
C17 C18 C19 121.9(3) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C14 119.2(3) . . ?
C18 C19 H19 120.4 . . ?
C14 C19 H19 120.4 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N22 C21 C25 101.12(18) . . ?
N22 C21 C9 111.91(19) . . ?
C25 C21 C9 115.16(19) . . ?
N22 C21 H21 109.4 . . ?
C25 C21 H21 109.4 . . ?
C9 C21 H21 109.4 . . ?
C28 N22 C21 119.69(19) . . ?
C28 N22 C23 127.4(2) . . ?
C21 N22 C23 112.22(18) . . ?
O24 C23 N22 101.20(18) . . ?
O24 C23 C26 107.3(2) . . ?
N22 C23 C26 114.0(2) . . ?
O24 C23 C27 109.5(2) . . ?
N22 C23 C27 111.4(2) . . ?
C26 C23 C27 112.7(2) . . ?
C25 O24 C23 108.59(17) . . ?
O24 C25 C21 104.61(19) . . ?
O24 C25 H25A 110.8 . . ?
C21 C25 H25A 110.8 . . ?
O24 C25 H25B 110.8 . . ?
C21 C25 H25B 110.8 . . ?
H25A C25 H25B 108.9 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O29 C28 O30 126.0(2) . . ?
O29 C28 N22 123.0(2) . . ?
O30 C28 N22 111.0(2) . . ?
C28 O30 C31 122.5(2) . . ?
O30 C31 C34 109.1(3) . . ?
O30 C31 C33 102.2(3) . . ?
C34 C31 C33 112.7(4) . . ?
O30 C31 C32 109.0(3) . . ?
C34 C31 C32 113.6(4) . . ?
C33 C31 C32 109.5(3) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
O2 P1 O3 C4 -33.6(3) . . . . ?
O6 P1 O3 C4 88.9(3) . . . . ?
C9 P1 O3 C4 -159.3(3) . . . . ?
P1 O3 C4 C5 95.1(4) . . . . ?
O2 P1 O6 C7 171.3(4) . . . . ?
O3 P1 O6 C7 44.2(4) . . . . ?
C9 P1 O6 C7 -64.9(4) . . . . ?
P1 O6 C7 C8 -171.8(5) . . . . ?
O2 P1 C9 N10 -66.1(2) . . . . ?
O3 P1 C9 N10 60.49(19) . . . . ?
O6 P1 C9 N10 174.19(17) . . . . ?
O2 P1 C9 C21 59.9(2) . . . . ?
O3 P1 C9 C21 -173.49(17) . . . . ?
O6 P1 C9 C21 -59.79(19) . . . . ?
C21 C9 N10 S11 115.2(2) . . . . ?
P1 C9 N10 S11 -119.63(17) . . . . ?
C9 N10 S11 O12 -15.7(2) . . . . ?
C9 N10 S11 O13 -146.47(19) . . . . ?
C9 N10 S11 C14 100.3(2) . . . . ?
O12 S11 C14 C15 -153.2(2) . . . . ?
O13 S11 C14 C15 -22.6(2) . . . . ?
N10 S11 C14 C15 90.9(2) . . . . ?
O12 S11 C14 C19 25.8(3) . . . . ?
O13 S11 C14 C19 156.3(2) . . . . ?
N10 S11 C14 C19 -90.2(2) . . . . ?
C19 C14 C15 C16 -0.5(4) . . . . ?
S11 C14 C15 C16 178.5(2) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C15 C16 C17 C20 179.1(3) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C20 C17 C18 C19 -179.5(3) . . . . ?
C17 C18 C19 C14 0.3(5) . . . . ?
C15 C14 C19 C18 0.1(5) . . . . ?
S11 C14 C19 C18 -178.9(3) . . . . ?
N10 C9 C21 N22 -63.5(2) . . . . ?
P1 C9 C21 N22 171.22(15) . . . . ?
N10 C9 C21 C25 51.2(3) . . . . ?
P1 C9 C21 C25 -74.0(2) . . . . ?
C25 C21 N22 C28 163.7(2) . . . . ?
C9 C21 N22 C28 -73.2(3) . . . . ?
C25 C21 N22 C23 -7.6(2) . . . . ?
C9 C21 N22 C23 115.5(2) . . . . ?
C28 N22 C23 O24 176.3(2) . . . . ?
C21 N22 C23 O24 -13.2(3) . . . . ?
C28 N22 C23 C26 61.5(3) . . . . ?
C21 N22 C23 C26 -128.0(2) . . . . ?
C28 N22 C23 C27 -67.4(3) . . . . ?
C21 N22 C23 C27 103.0(3) . . . . ?
N22 C23 O24 C25 30.7(2) . . . . ?
C26 C23 O24 C25 150.5(2) . . . . ?
C27 C23 O24 C25 -87.0(2) . . . . ?
C23 O24 C25 C21 -36.9(2) . . . . ?
N22 C21 C25 O24 25.8(2) . . . . ?
C9 C21 C25 O24 -95.0(2) . . . . ?
C21 N22 C28 O29 4.7(4) . . . . ?
C23 N22 C28 O29 174.6(3) . . . . ?
C21 N22 C28 O30 -174.0(2) . . . . ?
C23 N22 C28 O30 -4.1(4) . . . . ?
O29 C28 O30 C31 10.0(4) . . . . ?
N22 C28 O30 C31 -171.3(2) . . . . ?
C28 O30 C31 C34 58.5(4) . . . . ?
C28 O30 C31 C33 178.1(3) . . . . ?
C28 O30 C31 C32 -66.1(4) . . . . ?

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
C9 H9 O12 0.98 2.37 2.872(3) 111.3 .
C9 H9 O29 0.98 2.51 3.106(3) 118.7 .
N10 H10 O24 0.86 2.12 2.956(3) 163.4 2_655
C25 H25A O2 0.97 2.53 3.244(3) 130.3 .
C26 H26B O30 0.96 2.45 2.930(3) 110.8 .
C26 H26C O2 0.96 2.51 3.411(4) 156.3 2_655
C27 H27B O30 0.96 2.55 3.065(4) 113.4 .
C32 H32C O29 0.96 2.49 3.013(5) 114.2 .
C34 H34A O29 0.96 2.47 3.032(6) 117.2 .

_refine_diff_density_max         0.695
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_34
_database_code_depnum_ccdc_archive 'CCDC 1568456'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2018-03-14 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         'C24 H33 N2 O7 P S'
_chemical_formula_sum            'C24 H33 N2 O7 P S'
_chemical_formula_weight         524.55

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.1196(7)
_cell_length_b                   11.0522(9)
_cell_length_c                   13.6480(13)
_cell_angle_alpha                71.568(8)
_cell_angle_beta                 77.690(7)
_cell_angle_gamma                87.393(6)
_cell_volume                     1274.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    3219
_cell_measurement_theta_min      3.3390
_cell_measurement_theta_max      26.3990

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.236
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.83893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_measurement_method       '/w scan'
_diffrn_reflns_number            8392
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.312
_diffrn_reflns_theta_max         26.580
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4881
_reflns_number_gt                3446
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'



_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)+(0.0561P)²+6.6074P] 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         4881
_refine_ls_number_parameters     336
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0851
_refine_ls_wR_factor_ref         0.2050
_refine_ls_wR_factor_gt          0.1902
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.022
_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 0.41164(13) 0.73518(12) 0.98315(9) 0.0227(3) Uani 1 1 d . . . . .
O2 O 0.4250(4) 0.6091(3) 1.0608(3) 0.0301(8) Uani 1 1 d . . . . .
O3 O 0.4801(4) 0.8496(3) 1.0048(3) 0.0321(8) Uani 1 1 d . . . . .
C4A C 0.4633(10) 0.8510(10) 1.1093(7) 0.028(2) Uani 0.5 1 d D . P A 1
H4A H 0.3949 0.7801 1.1576 0.034 Uiso 0.5 1 calc R U P A 1
H4B H 0.4184 0.9322 1.1155 0.034 Uiso 0.5 1 calc R U P A 1
C5A C 0.6161(12) 0.8369(14) 1.1408(12) 0.046(3) Uani 0.5 1 d D U P A 1
H5A H 0.6032 0.8378 1.2137 0.068 Uiso 0.5 1 calc R U P A 1
H5B H 0.6832 0.9078 1.0935 0.068 Uiso 0.5 1 calc R U P A 1
H5C H 0.6599 0.7560 1.1354 0.068 Uiso 0.5 1 calc R U P A 1
C4B C 0.6006(11) 0.8347(11) 1.0623(7) 0.034(2) Uani 0.5 1 d D . P A 2
H4C H 0.6807 0.8998 1.0221 0.040 Uiso 0.5 1 calc R U P A 2
H4D H 0.6445 0.7494 1.0704 0.040 Uiso 0.5 1 calc R U P A 2
C5B C 0.5401(15) 0.8495(12) 1.1715(7) 0.035(3) Uani 0.5 1 d D U P A 2
H5D H 0.6221 0.8393 1.2095 0.052 Uiso 0.5 1 calc R U P A 2
H5E H 0.4618 0.7842 1.2116 0.052 Uiso 0.5 1 calc R U P A 2
H5F H 0.4978 0.9343 1.1634 0.052 Uiso 0.5 1 calc R U P A 2
O6 O 0.2465(4) 0.7779(3) 0.9804(3) 0.0309(8) Uani 1 1 d . . . . .
C7 C 0.1301(5) 0.6842(5) 0.9876(4) 0.0307(12) Uani 1 1 d . . . . .
H7B H 0.1713 0.5973 1.0029 0.037 Uiso 1 1 calc R U . . .
H7A H 0.0963 0.7056 0.9199 0.037 Uiso 1 1 calc R U . . .
C8 C 0.0013(5) 0.6896(5) 1.0748(4) 0.0340(12) Uani 1 1 d . . . . .
H8C H -0.0368 0.7765 1.0598 0.051 Uiso 1 1 calc R U . . .
H8B H 0.0353 0.6655 1.1418 0.051 Uiso 1 1 calc R U . . .
H8A H -0.0789 0.6304 1.0801 0.051 Uiso 1 1 calc R U . . .
C9 C 0.5036(5) 0.7424(5) 0.8492(4) 0.0291(11) Uani 1 1 d . . . . .
H9 H 0.4493 0.8090 0.8024 0.035 Uiso 1 1 calc R U . . .
N10 N 0.4683(5) 0.6288(5) 0.8365(4) 0.0407(12) Uani 1 1 d . . . . .
H10 H 0.4976 0.5579 0.8784 0.049 Uiso 1 1 calc R U . . .
S11 S 0.37471(15) 0.61540(14) 0.74819(11) 0.0348(4) Uani 1 1 d . . . . .
O12 O 0.2898(5) 0.7197(4) 0.7171(4) 0.0597(13) Uani 1 1 d . . . . .
O13 O 0.3066(4) 0.4934(4) 0.8015(3) 0.0514(12) Uani 1 1 d . . . . .
C14 C 0.5111(5) 0.6032(5) 0.6404(4) 0.0274(11) Uani 1 1 d . . . . .
C15 C 0.6063(7) 0.5012(6) 0.6561(5) 0.0450(15) Uani 1 1 d . . . . .
H15 H 0.5980 0.4390 0.7236 0.054 Uiso 1 1 calc R U . . .
C16 C 0.7172(7) 0.4923(8) 0.5681(8) 0.068(2) Uani 1 1 d . . . . .
H16 H 0.7817 0.4214 0.5765 0.081 Uiso 1 1 calc R U . . .
C17 C 0.7325(9) 0.5844(10) 0.4713(6) 0.068(2) Uani 1 1 d . . . . .
C18 C 0.6366(8) 0.6827(9) 0.4600(5) 0.065(2) Uani 1 1 d . . . . .
H18 H 0.6457 0.7459 0.3929 0.078 Uiso 1 1 calc R U . . .
C19 C 0.5266(6) 0.6938(6) 0.5424(4) 0.0415(14) Uani 1 1 d . . . . .
H19 H 0.4611 0.7640 0.5320 0.050 Uiso 1 1 calc R U . . .
C20 C 0.8562(9) 0.5752(12) 0.3787(8) 0.125(5) Uani 1 1 d . . . . .
H20C H 0.8129 0.5865 0.3167 0.187 Uiso 1 1 calc R U . . .
H20B H 0.9019 0.4912 0.3978 0.187 Uiso 1 1 calc R U . . .
H20A H 0.9330 0.6418 0.3625 0.187 Uiso 1 1 calc R U . . .
C21 C 0.6667(5) 0.7890(4) 0.8165(3) 0.0208(10) Uani 1 1 d . . . . .
H21 H 0.6719 0.8745 0.8264 0.025 Uiso 1 1 calc R U . . .
N22 N 0.7317(4) 0.8008(4) 0.7058(3) 0.0215(8) Uani 1 1 d . . . . .
C23 C 0.8658(5) 0.7233(4) 0.6927(4) 0.0247(10) Uani 1 1 d . . . . .
H23B H 0.9590 0.7760 0.6721 0.030 Uiso 1 1 calc R U . . .
H23A H 0.8645 0.6807 0.6391 0.030 Uiso 1 1 calc R U . . .
C24 C 0.8524(5) 0.6266(5) 0.8020(4) 0.0292(11) Uani 1 1 d . . . . .
H24B H 0.9525 0.5980 0.8162 0.035 Uiso 1 1 calc R U . . .
H24A H 0.7907 0.5513 0.8100 0.035 Uiso 1 1 calc R U . . .
C25 C 0.7756(5) 0.7007(5) 0.8754(4) 0.0283(11) Uani 1 1 d . . . . .
H25B H 0.8505 0.7509 0.8903 0.034 Uiso 1 1 calc R U . . .
H25A H 0.7208 0.6418 0.9431 0.034 Uiso 1 1 calc R U . . .
C26 C 0.6979(5) 0.8990(5) 0.6266(3) 0.0235(10) Uani 1 1 d . . . . .
O27 O 0.5967(4) 0.9737(3) 0.6352(3) 0.0295(8) Uani 1 1 d . . . . .
O28 O 0.7918(3) 0.9010(3) 0.5348(2) 0.0262(8) Uani 1 1 d . . . . .
C29 C 0.7660(6) 0.9964(5) 0.4402(4) 0.0308(12) Uani 1 1 d . . . . .
H29B H 0.7793 1.0831 0.4439 0.037 Uiso 1 1 calc R U . . .
H29A H 0.6629 0.9872 0.4306 0.037 Uiso 1 1 calc R U . . .
C30 C 0.8808(6) 0.9739(4) 0.3500(4) 0.0282(11) Uani 1 1 d . . . . .
C31 C 0.8481(6) 1.0086(5) 0.2506(4) 0.0337(12) Uani 1 1 d . . . . .
H31 H 0.7540 1.0446 0.2400 0.040 Uiso 1 1 calc R U . . .
C32 C 0.9526(7) 0.9908(5) 0.1662(4) 0.0408(14) Uani 1 1 d . . . . .
H32 H 0.9296 1.0150 0.0980 0.049 Uiso 1 1 calc R U . . .
C33 C 1.0897(7) 0.9381(5) 0.1808(4) 0.0399(14) Uani 1 1 d . . . . .
H33 H 1.1606 0.9254 0.1232 0.048 Uiso 1 1 calc R U . . .
C34 C 1.1228(6) 0.9044(5) 0.2795(4) 0.0381(13) Uani 1 1 d . . . . .
H34 H 1.2174 0.8691 0.2897 0.046 Uiso 1 1 calc R U . . .
C35 C 1.0189(5) 0.9215(5) 0.3644(4) 0.0341(12) Uani 1 1 d . . . . .
H35 H 1.0424 0.8974 0.4325 0.041 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 O2 1.478(3) . ?
P1 O6 1.562(3) . ?
P1 O3 1.569(4) . ?
P1 C9 1.819(5) . ?
O3 C4A 1.407(10) . ?
O3 C4B 1.457(11) . ?
C4A C5A 1.531(5) . ?
C4A H4A 0.9900 . ?
C4A H4B 0.9900 . ?
C5A H5A 0.9800 . ?
C5A H5B 0.9800 . ?
C5A H5C 0.9800 . ?
C4B C5B 1.532(5) . ?
C4B H4C 0.9900 . ?
C4B H4D 0.9900 . ?
C5B H5D 0.9800 . ?
C5B H5E 0.9800 . ?
C5B H5F 0.9800 . ?
O6 C7 1.483(6) . ?
C7 C8 1.498(7) . ?
C7 H7B 0.9900 . ?
C7 H7A 0.9900 . ?
C8 H8C 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8A 0.9800 . ?
C9 N10 1.383(7) . ?
C9 C21 1.522(6) . ?
C9 H9 1.0000 . ?
N10 S11 1.663(5) . ?
N10 H10 0.8800 . ?
S11 O12 1.363(5) . ?
S11 O13 1.413(4) . ?
S11 C14 1.750(5) . ?
C14 C19 1.377(7) . ?
C14 C15 1.381(8) . ?
C15 C16 1.421(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(12) . ?
C16 H16 0.9500 . ?
C17 C18 1.354(11) . ?
C17 C20 1.530(9) . ?
C18 C19 1.372(9) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20C 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20A 0.9800 . ?
C21 N22 1.468(5) . ?
C21 C25 1.530(6) . ?
C21 H21 1.0000 . ?
N22 C26 1.345(6) . ?
N22 C23 1.472(6) . ?
C23 C24 1.520(6) . ?
C23 H23B 0.9900 . ?
C23 H23A 0.9900 . ?
C24 C25 1.527(7) . ?
C24 H24B 0.9900 . ?
C24 H24A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 H25A 0.9900 . ?
C26 O27 1.222(6) . ?
C26 O28 1.354(5) . ?
O28 C29 1.442(6) . ?
C29 C30 1.514(7) . ?
C29 H29B 0.9900 . ?
C29 H29A 0.9900 . ?
C30 C31 1.381(7) . ?
C30 C35 1.388(7) . ?
C31 C32 1.391(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.381(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.374(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.390(7) . ?
C34 H34 0.9500 . ?
C35 H35 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
O2 P1 O6 114.25(19) . . ?
O2 P1 O3 114.5(2) . . ?
O6 P1 O3 101.7(2) . . ?
O2 P1 C9 112.4(2) . . ?
O6 P1 C9 107.2(2) . . ?
O3 P1 C9 105.8(2) . . ?
C4A O3 P1 119.6(5) . . ?
C4B O3 P1 122.9(5) . . ?
O3 C4A C5A 110.1(8) . . ?
O3 C4A H4A 109.6 . . ?
C5A C4A H4A 109.6 . . ?
O3 C4A H4B 109.6 . . ?
C5A C4A H4B 109.6 . . ?
H4A C4A H4B 108.1 . . ?
C4A C5A H5A 109.5 . . ?
C4A C5A H5B 109.5 . . ?
H5A C5A H5B 109.5 . . ?
C4A C5A H5C 109.5 . . ?
H5A C5A H5C 109.5 . . ?
H5B C5A H5C 109.5 . . ?
O3 C4B C5B 110.2(8) . . ?
O3 C4B H4C 109.6 . . ?
C5B C4B H4C 109.6 . . ?
O3 C4B H4D 109.6 . . ?
C5B C4B H4D 109.6 . . ?
H4C C4B H4D 108.1 . . ?
C4B C5B H5D 109.5 . . ?
C4B C5B H5E 109.5 . . ?
H5D C5B H5E 109.5 . . ?
C4B C5B H5F 109.5 . . ?
H5D C5B H5F 109.5 . . ?
H5E C5B H5F 109.5 . . ?
C7 O6 P1 120.0(3) . . ?
O6 C7 C8 107.6(4) . . ?
O6 C7 H7B 110.2 . . ?
C8 C7 H7B 110.2 . . ?
O6 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
H7B C7 H7A 108.5 . . ?
C7 C8 H8C 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8C C8 H8B 109.5 . . ?
C7 C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
H8B C8 H8A 109.5 . . ?
N10 C9 C21 118.9(4) . . ?
N10 C9 P1 106.5(3) . . ?
C21 C9 P1 114.8(3) . . ?
N10 C9 H9 105.1 . . ?
C21 C9 H9 105.1 . . ?
P1 C9 H9 105.1 . . ?
C9 N10 S11 125.1(4) . . ?
C9 N10 H10 117.4 . . ?
S11 N10 H10 117.4 . . ?
O12 S11 O13 120.8(3) . . ?
O12 S11 N10 111.2(3) . . ?
O13 S11 N10 100.2(2) . . ?
O12 S11 C14 109.9(3) . . ?
O13 S11 C14 107.7(3) . . ?
N10 S11 C14 105.9(2) . . ?
C19 C14 C15 120.2(5) . . ?
C19 C14 S11 121.4(4) . . ?
C15 C14 S11 118.3(4) . . ?
C14 C15 C16 118.0(6) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C17 C16 C15 121.1(7) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 118.6(6) . . ?
C18 C17 C20 121.3(9) . . ?
C16 C17 C20 120.1(9) . . ?
C17 C18 C19 122.1(7) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C18 C19 C14 119.9(7) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C17 C20 H20C 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20C C20 H20B 109.5 . . ?
C17 C20 H20A 109.5 . . ?
H20C C20 H20A 109.5 . . ?
H20B C20 H20A 109.5 . . ?
N22 C21 C9 112.3(4) . . ?
N22 C21 C25 102.6(4) . . ?
C9 C21 C25 115.5(4) . . ?
N22 C21 H21 108.7 . . ?
C9 C21 H21 108.7 . . ?
C25 C21 H21 108.7 . . ?
C26 N22 C21 121.0(4) . . ?
C26 N22 C23 123.0(4) . . ?
C21 N22 C23 113.3(4) . . ?
N22 C23 C24 102.8(4) . . ?
N22 C23 H23B 111.2 . . ?
C24 C23 H23B 111.2 . . ?
N22 C23 H23A 111.2 . . ?
C24 C23 H23A 111.2 . . ?
H23B C23 H23A 109.1 . . ?
C23 C24 C25 103.3(4) . . ?
C23 C24 H24B 111.1 . . ?
C25 C24 H24B 111.1 . . ?
C23 C24 H24A 111.1 . . ?
C25 C24 H24A 111.1 . . ?
H24B C24 H24A 109.1 . . ?
C24 C25 C21 105.7(4) . . ?
C24 C25 H25B 110.6 . . ?
C21 C25 H25B 110.6 . . ?
C24 C25 H25A 110.6 . . ?
C21 C25 H25A 110.6 . . ?
H25B C25 H25A 108.7 . . ?
O27 C26 N22 125.8(4) . . ?
O27 C26 O28 124.9(4) . . ?
N22 C26 O28 109.4(4) . . ?
C26 O28 C29 116.8(4) . . ?
O28 C29 C30 105.9(4) . . ?
O28 C29 H29B 110.6 . . ?
C30 C29 H29B 110.6 . . ?
O28 C29 H29A 110.6 . . ?
C30 C29 H29A 110.6 . . ?
H29B C29 H29A 108.7 . . ?
C31 C30 C35 119.3(5) . . ?
C31 C30 C29 119.0(5) . . ?
C35 C30 C29 121.6(5) . . ?
C30 C31 C32 120.2(5) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C33 C32 C31 120.4(5) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 119.5(5) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C33 C34 C35 120.5(5) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C30 C35 C34 120.1(5) . . ?
C30 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?

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 O3 C4A -38.5(5) . . . . ?
O6 P1 O3 C4A 85.2(5) . . . . ?
C9 P1 O3 C4A -162.9(5) . . . . ?
O2 P1 O3 C4B 26.1(5) . . . . ?
O6 P1 O3 C4B 149.9(5) . . . . ?
C9 P1 O3 C4B -98.3(5) . . . . ?
C4B O3 C4A C5A 1.9(9) . . . . ?
P1 O3 C4A C5A 113.1(8) . . . . ?
C4A O3 C4B C5B -3.4(8) . . . . ?
P1 O3 C4B C5B -108.5(8) . . . . ?
O2 P1 O6 C7 -41.3(4) . . . . ?
O3 P1 O6 C7 -165.2(3) . . . . ?
C9 P1 O6 C7 84.0(4) . . . . ?
P1 O6 C7 C8 127.4(4) . . . . ?
O2 P1 C9 N10 42.3(4) . . . . ?
O6 P1 C9 N10 -84.0(4) . . . . ?
O3 P1 C9 N10 168.0(3) . . . . ?
O2 P1 C9 C21 -91.5(4) . . . . ?
O6 P1 C9 C21 142.2(4) . . . . ?
O3 P1 C9 C21 34.3(4) . . . . ?
C21 C9 N10 S11 -109.7(5) . . . . ?
P1 C9 N10 S11 118.8(4) . . . . ?
C9 N10 S11 O12 -22.7(5) . . . . ?
C9 N10 S11 O13 -151.5(4) . . . . ?
C9 N10 S11 C14 96.7(5) . . . . ?
O12 S11 C14 C19 2.8(5) . . . . ?
O13 S11 C14 C19 136.2(4) . . . . ?
N10 S11 C14 C19 -117.3(4) . . . . ?
O12 S11 C14 C15 -178.6(4) . . . . ?
O13 S11 C14 C15 -45.3(5) . . . . ?
N10 S11 C14 C15 61.2(5) . . . . ?
C19 C14 C15 C16 -1.2(8) . . . . ?
S11 C14 C15 C16 -179.8(4) . . . . ?
C14 C15 C16 C17 2.1(9) . . . . ?
C15 C16 C17 C18 -2.0(10) . . . . ?
C15 C16 C17 C20 177.9(6) . . . . ?
C16 C17 C18 C19 1.0(10) . . . . ?
C20 C17 C18 C19 -178.9(6) . . . . ?
C17 C18 C19 C14 -0.1(10) . . . . ?
C15 C14 C19 C18 0.2(8) . . . . ?
S11 C14 C19 C18 178.8(5) . . . . ?
N10 C9 C21 N22 56.0(6) . . . . ?
P1 C9 C21 N22 -176.3(3) . . . . ?
N10 C9 C21 C25 -61.2(6) . . . . ?
P1 C9 C21 C25 66.6(5) . . . . ?
C9 C21 N22 C26 76.0(5) . . . . ?
C25 C21 N22 C26 -159.4(4) . . . . ?
C9 C21 N22 C23 -122.0(4) . . . . ?
C25 C21 N22 C23 2.6(5) . . . . ?
C26 N22 C23 C24 -179.5(4) . . . . ?
C21 N22 C23 C24 18.9(5) . . . . ?
N22 C23 C24 C25 -32.1(5) . . . . ?
C23 C24 C25 C21 35.0(5) . . . . ?
N22 C21 C25 C24 -23.2(5) . . . . ?
C9 C21 C25 C24 99.3(5) . . . . ?
C21 N22 C26 O27 -12.4(7) . . . . ?
C23 N22 C26 O27 -172.6(5) . . . . ?
C21 N22 C26 O28 168.9(4) . . . . ?
C23 N22 C26 O28 8.7(6) . . . . ?
O27 C26 O28 C29 -2.1(7) . . . . ?
N22 C26 O28 C29 176.7(4) . . . . ?
C26 O28 C29 C30 -177.7(4) . . . . ?
O28 C29 C30 C31 152.3(4) . . . . ?
O28 C29 C30 C35 -28.9(6) . . . . ?
C35 C30 C31 C32 0.1(8) . . . . ?
C29 C30 C31 C32 179.0(5) . . . . ?
C30 C31 C32 C33 0.2(8) . . . . ?
C31 C32 C33 C34 -0.6(8) . . . . ?
C32 C33 C34 C35 0.7(8) . . . . ?
C31 C30 C35 C34 0.0(8) . . . . ?
C29 C30 C35 C34 -178.8(5) . . . . ?
C33 C34 C35 C30 -0.5(8) . . . . ?

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
C4A H4B O3 0.99 2.53 3.193(11) 123.9 2_677
C8 H8A O13 0.98 2.50 3.341(6) 144.4 2_567
C9 H9 O12 1.00 2.46 2.992(7) 113.0 .
C9 H9 O27 1.00 2.57 3.195(6) 120.3 .
N10 H10 O2 0.88 1.94 2.801(6) 166.0 2_667
C24 H24A O2 0.99 2.64 3.491(6) 143.8 2_667

_refine_diff_density_max         1.806
_refine_diff_density_min         -1.024
_refine_diff_density_rms         0.091

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_23a
_database_code_depnum_ccdc_archive 'CCDC 1568455'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2018-03-14 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         'C22 H28 F3 N2 O5 P S'
_chemical_formula_sum            'C22 H28 F3 N2 O5 P S'
_chemical_formula_weight         520.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.4187(3)
_cell_length_b                   11.5503(5)
_cell_length_c                   25.4175(10)
_cell_angle_alpha                90.406(3)
_cell_angle_beta                 99.189(3)
_cell_angle_gamma                113.524(4)
_cell_volume                     2495.13(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    6595
_cell_measurement_theta_min      3.2104
_cell_measurement_theta_max      26.5858

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.251
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.97159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_measurement_method       '/w scan'
_diffrn_reflns_number            18335
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.217
_diffrn_reflns_theta_max         26.644
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9637
_reflns_number_gt                7875
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.0442P)²+1.5465P] 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_number_reflns         9637
_refine_ls_number_parameters     627
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
P1A P 1.07322(6) 0.70753(4) -0.00911(2) 0.02027(11) Uani 1 1 d . . . . .
O2A O 1.06778(16) 0.60542(12) -0.04539(5) 0.0256(3) Uani 1 1 d . . . . .
O3A O 1.16811(15) 0.72206(14) 0.04897(5) 0.0295(3) Uani 1 1 d . . . . .
C4A C 1.3373(3) 0.7570(3) 0.05684(10) 0.0510(7) Uani 1 1 d . . . . .
H4A1 H 1.3581 0.6860 0.0431 0.061 Uiso 1 1 calc R U . . .
H4A2 H 1.3872 0.8313 0.0367 0.061 Uiso 1 1 calc R U . . .
C5A C 1.4039(3) 0.7870(3) 0.11285(10) 0.0554(7) Uani 1 1 d . . . . .
H5A1 H 1.3777 0.8539 0.1268 0.083 Uiso 1 1 calc R U . . .
H5A2 H 1.5185 0.8162 0.1176 0.083 Uiso 1 1 calc R U . . .
H5A3 H 1.3608 0.7112 0.1323 0.083 Uiso 1 1 calc R U . . .
O6A O 1.14543(16) 0.84270(12) -0.02973(5) 0.0252(3) Uani 1 1 d . . . . .
C7A C 1.1914(2) 0.8641(2) -0.08215(8) 0.0297(4) Uani 1 1 d . . . . .
H7A1 H 1.1351 0.7857 -0.1062 0.036 Uiso 1 1 calc R U . . .
H7A2 H 1.3059 0.8875 -0.0788 0.036 Uiso 1 1 calc R U . . .
C8A C 1.1514(3) 0.9687(2) -0.10494(9) 0.0384(5) Uani 1 1 d . . . . .
H8A1 H 1.0373 0.9432 -0.1099 0.058 Uiso 1 1 calc R U . . .
H8A2 H 1.1861 0.9863 -0.1395 0.058 Uiso 1 1 calc R U . . .
H8A3 H 1.2045 1.0451 -0.0803 0.058 Uiso 1 1 calc R U . . .
C9A C 0.8817(2) 0.68671(17) 0.00578(7) 0.0199(4) Uani 1 1 d . . . . .
H9A H 0.8891 0.7689 0.0216 0.024 Uiso 1 1 calc R U . . .
N10A N 0.82909(19) 0.58952(15) 0.04333(6) 0.0211(3) Uani 1 1 d . . . . .
H10A H 0.853(3) 0.530(2) 0.0438(9) 0.036(7) Uiso 1 1 d . . . . .
S11A S 0.78049(5) 0.61677(4) 0.09858(2) 0.02127(11) Uani 1 1 d . . . . .
O12A O 0.72248(16) 0.71377(14) 0.09086(5) 0.0304(3) Uani 1 1 d . . . . .
O13A O 0.68204(15) 0.49543(13) 0.11394(5) 0.0290(3) Uani 1 1 d . . . . .
C14A C 0.9503(2) 0.67473(18) 0.14892(7) 0.0219(4) Uani 1 1 d . . . . .
C15A C 1.0138(2) 0.79855(19) 0.17043(8) 0.0303(4) Uani 1 1 d . . . . .
H15A H 0.9721 0.8567 0.1563 0.036 Uiso 1 1 calc R U . . .
C16A C 1.1392(3) 0.8371(2) 0.21297(8) 0.0344(5) Uani 1 1 d . . . . .
H16A H 1.1839 0.9225 0.2276 0.041 Uiso 1 1 calc R U . . .
C17A C 1.2002(2) 0.7538(2) 0.23444(7) 0.0281(4) Uani 1 1 d . . . . .
C18A C 1.1372(2) 0.6301(2) 0.21103(8) 0.0287(4) Uani 1 1 d . . . . .
H18A H 1.1800 0.5723 0.2246 0.034 Uiso 1 1 calc R U . . .
C19A C 1.0136(2) 0.59057(18) 0.16845(8) 0.0261(4) Uani 1 1 d . . . . .
H19A H 0.9722 0.5063 0.1526 0.031 Uiso 1 1 calc R U . . .
C20A C 1.3286(3) 0.7922(2) 0.28300(9) 0.0402(5) Uani 1 1 d . . . . .
H20A H 1.3531 0.8792 0.2962 0.060 Uiso 1 1 calc R U . . .
H20B H 1.4229 0.7874 0.2734 0.060 Uiso 1 1 calc R U . . .
H20C H 1.2932 0.7350 0.3110 0.060 Uiso 1 1 calc R U . . .
C21A C 0.7587(2) 0.64582(17) -0.04552(7) 0.0220(4) Uani 1 1 d . . . . .
H21A H 0.6945 0.5523 -0.0504 0.026 Uiso 1 1 calc R U . . .
N22A N 0.80185(18) 0.70092(14) -0.09514(6) 0.0210(3) Uani 1 1 d . . . . .
C23A C 0.6765(2) 0.71984(19) -0.07415(7) 0.0245(4) Uani 1 1 d . . . . .
H23A H 0.5678 0.6680 -0.0938 0.029 Uiso 1 1 calc R U . . .
C24A C 0.7073(2) 0.8528(2) -0.05793(8) 0.0313(5) Uani 1 1 d . . . . .
F25A F 0.85293(14) 0.92175(11) -0.03303(5) 0.0327(3) Uani 1 1 d . . . . .
F26A F 0.61078(17) 0.85699(15) -0.02506(6) 0.0586(4) Uani 1 1 d . . . . .
F27A F 0.6809(2) 0.91432(14) -0.10035(6) 0.0580(4) Uani 1 1 d . . . . .
C28A C 0.7497(3) 0.60836(19) -0.14199(7) 0.0280(4) Uani 1 1 d . . . . .
H28A H 0.6444 0.5421 -0.1403 0.034 Uiso 1 1 calc R U . . .
H28B H 0.8238 0.5669 -0.1415 0.034 Uiso 1 1 calc R U . . .
C29A C 0.7426(2) 0.67276(19) -0.19310(7) 0.0245(4) Uani 1 1 d . . . . .
C30A C 0.6016(2) 0.6724(2) -0.21886(8) 0.0326(5) Uani 1 1 d . . . . .
H30A H 0.5085 0.6292 -0.2046 0.039 Uiso 1 1 calc R U . . .
C31A C 0.5939(3) 0.7340(2) -0.26510(9) 0.0382(5) Uani 1 1 d . . . . .
H31A H 0.4959 0.7331 -0.2821 0.046 Uiso 1 1 calc R U . . .
C32A C 0.7268(3) 0.7965(2) -0.28652(8) 0.0373(5) Uani 1 1 d . . . . .
H32A H 0.7216 0.8390 -0.3181 0.045 Uiso 1 1 calc R U . . .
C33A C 0.8682(3) 0.7965(2) -0.26148(9) 0.0421(6) Uani 1 1 d . . . . .
H33A H 0.9608 0.8390 -0.2761 0.051 Uiso 1 1 calc R U . . .
C34A C 0.8758(3) 0.7351(2) -0.21525(8) 0.0371(5) Uani 1 1 d . . . . .
H34A H 0.9737 0.7356 -0.1985 0.045 Uiso 1 1 calc R U . . .
P1B P -0.07154(6) 0.79613(5) 0.51942(2) 0.02642(13) Uani 1 1 d . . . . .
O2B O -0.05704(17) 0.90638(14) 0.55268(5) 0.0333(3) Uani 1 1 d . . . . .
O3B O -0.14640(17) 0.66697(14) 0.54434(6) 0.0351(3) Uani 1 1 d . . . . .
C4B C -0.1802(3) 0.6611(3) 0.59852(10) 0.0523(7) Uani 1 1 d . . . . .
H4B1 H -0.0807 0.7032 0.6243 0.063 Uiso 1 1 calc R U . . .
H4B2 H -0.2476 0.7072 0.6021 0.063 Uiso 1 1 calc R U . . .
C5B C -0.2561(7) 0.5365(3) 0.61061(16) 0.137(2) Uani 1 1 d . . . . .
H5B1 H -0.3571 0.4960 0.5863 0.206 Uiso 1 1 calc R U . . .
H5B2 H -0.2742 0.5353 0.6475 0.206 Uiso 1 1 calc R U . . .
H5B3 H -0.1903 0.4904 0.6065 0.206 Uiso 1 1 calc R U . . .
O6B O -0.17037(16) 0.77474(15) 0.46189(5) 0.0354(4) Uani 1 1 d . . . . .
C7B C -0.3351(2) 0.7556(2) 0.45489(9) 0.0372(5) Uani 1 1 d . . . . .
H7B1 H -0.3458 0.8243 0.4751 0.045 Uiso 1 1 calc R U . . .
H7B2 H -0.3981 0.6737 0.4682 0.045 Uiso 1 1 calc R U . . .
C8B C -0.3913(3) 0.7558(2) 0.39684(9) 0.0385(5) Uani 1 1 d . . . . .
H8B1 H -0.3241 0.8350 0.3836 0.058 Uiso 1 1 calc R U . . .
H8B2 H -0.5000 0.7486 0.3911 0.058 Uiso 1 1 calc R U . . .
H8B3 H -0.3869 0.6840 0.3775 0.058 Uiso 1 1 calc R U . . .
C9B C 0.1152(2) 0.80851(19) 0.50295(7) 0.0248(4) Uani 1 1 d . . . . .
H9B H 0.1035 0.7239 0.4884 0.030 Uiso 1 1 calc R U . . .
N10B N 0.1649(2) 0.90090(18) 0.46335(6) 0.0263(4) Uani 1 1 d . . . . .
H10B H 0.139(3) 0.958(2) 0.4614(9) 0.024(6) Uiso 1 1 d . . . . .
S11B S 0.20903(6) 0.86647(5) 0.40824(2) 0.02791(12) Uani 1 1 d . . . . .
O12B O 0.31321(17) 0.98350(15) 0.39155(6) 0.0386(4) Uani 1 1 d . . . . .
O13B O 0.25769(18) 0.76441(16) 0.41765(6) 0.0389(4) Uani 1 1 d . . . . .
C14B C 0.0375(2) 0.81017(19) 0.35872(7) 0.0253(4) Uani 1 1 d . . . . .
C15B C -0.0059(2) 0.8968(2) 0.33060(8) 0.0312(5) Uani 1 1 d . . . . .
H15B H 0.0534 0.9851 0.3390 0.037 Uiso 1 1 calc R U . . .
C16B C -0.1362(3) 0.8533(2) 0.29014(8) 0.0341(5) Uani 1 1 d . . . . .
H16B H -0.1650 0.9127 0.2705 0.041 Uiso 1 1 calc R U . . .
C17B C -0.2258(2) 0.7247(2) 0.27765(8) 0.0319(5) Uani 1 1 d . . . . .
C18B C -0.1827(3) 0.6406(2) 0.30748(9) 0.0359(5) Uani 1 1 d . . . . .
H18B H -0.2445 0.5523 0.3002 0.043 Uiso 1 1 calc R U . . .
C19B C -0.0518(3) 0.6817(2) 0.34771(8) 0.0333(5) Uani 1 1 d . . . . .
H19B H -0.0236 0.6223 0.3675 0.040 Uiso 1 1 calc R U . . .
C20B C -0.3658(3) 0.6781(3) 0.23274(9) 0.0463(6) Uani 1 1 d . . . . .
H20D H -0.3791 0.7507 0.2166 0.069 Uiso 1 1 calc R U . . .
H20E H -0.4606 0.6265 0.2468 0.069 Uiso 1 1 calc R U . . .
H20F H -0.3487 0.6267 0.2056 0.069 Uiso 1 1 calc R U . . .
C21B C 0.2428(2) 0.85286(19) 0.55312(7) 0.0259(4) Uani 1 1 d . . . . .
H21B H 0.3069 0.9464 0.5569 0.031 Uiso 1 1 calc R U . . .
N22B N 0.20517(19) 0.79979(15) 0.60361(6) 0.0249(3) Uani 1 1 d . . . . .
C23B C 0.3270(2) 0.7794(2) 0.58091(8) 0.0287(4) Uani 1 1 d . . . . .
H23B H 0.4372 0.8315 0.5993 0.034 Uiso 1 1 calc R U . . .
C24B C 0.2942(3) 0.6459(2) 0.56496(9) 0.0366(5) Uani 1 1 d . . . . .
F25B F 0.37678(19) 0.63926(15) 0.52771(6) 0.0591(4) Uani 1 1 d . . . . .
F26B F 0.33554(19) 0.58838(14) 0.60689(6) 0.0529(4) Uani 1 1 d . . . . .
F27B F 0.14388(16) 0.57434(12) 0.54563(6) 0.0459(3) Uani 1 1 d . . . . .
C28B C 0.2589(3) 0.89346(19) 0.64979(7) 0.0291(4) Uani 1 1 d . . . . .
H28C H 0.1873 0.9374 0.6482 0.035 Uiso 1 1 calc R U . . .
H28D H 0.3653 0.9576 0.6478 0.035 Uiso 1 1 calc R U . . .
C29B C 0.2641(2) 0.83409(18) 0.70246(7) 0.0248(4) Uani 1 1 d . . . . .
C30B C 0.1885(2) 0.70491(19) 0.70651(8) 0.0278(4) Uani 1 1 d . . . . .
H30B H 0.1307 0.6504 0.6753 0.033 Uiso 1 1 calc R U . . .
C31B C 0.1964(2) 0.6545(2) 0.75578(8) 0.0318(5) Uani 1 1 d . . . . .
H31B H 0.1438 0.5658 0.7580 0.038 Uiso 1 1 calc R U . . .
C32B C 0.2802(3) 0.7321(2) 0.80163(8) 0.0327(5) Uani 1 1 d . . . . .
H32B H 0.2859 0.6971 0.8352 0.039 Uiso 1 1 calc R U . . .
C33B C 0.3555(3) 0.8608(2) 0.79804(8) 0.0345(5) Uani 1 1 d . . . . .
H33B H 0.4131 0.9149 0.8293 0.041 Uiso 1 1 calc R U . . .
C34B C 0.3475(2) 0.9116(2) 0.74891(8) 0.0308(5) Uani 1 1 d . . . . .
H34B H 0.3996 1.0004 0.7469 0.037 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
P1A O2A 1.4717(13) . ?
P1A O6A 1.5661(13) . ?
P1A O3A 1.5689(14) . ?
P1A C9A 1.8243(18) . ?
O3A C4A 1.458(3) . ?
C4A C5A 1.440(3) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A H5A1 0.9800 . ?
C5A H5A2 0.9800 . ?
C5A H5A3 0.9800 . ?
O6A C7A 1.459(2) . ?
C7A C8A 1.497(3) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C9A N10A 1.462(2) . ?
C9A C21A 1.529(2) . ?
C9A H9A 1.0000 . ?
N10A S11A 1.6109(16) . ?
N10A H10A 0.80(2) . ?
S11A O12A 1.4316(14) . ?
S11A O13A 1.4361(14) . ?
S11A C14A 1.7672(19) . ?
C14A C15A 1.380(3) . ?
C14A C19A 1.386(3) . ?
C15A C16A 1.389(3) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.379(3) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.395(3) . ?
C17A C20A 1.507(3) . ?
C18A C19A 1.379(3) . ?
C18A H18A 0.9500 . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C21A N22A 1.459(2) . ?
C21A C23A 1.489(3) . ?
C21A H21A 1.0000 . ?
N22A C23A 1.460(2) . ?
N22A C28A 1.476(2) . ?
C23A C24A 1.487(3) . ?
C23A H23A 1.0000 . ?
C24A F25A 1.326(2) . ?
C24A F27A 1.340(2) . ?
C24A F26A 1.343(2) . ?
C28A C29A 1.507(3) . ?
C28A H28A 0.9900 . ?
C28A H28B 0.9900 . ?
C29A C30A 1.382(3) . ?
C29A C34A 1.385(3) . ?
C30A C31A 1.385(3) . ?
C30A H30A 0.9500 . ?
C31A C32A 1.374(3) . ?
C31A H31A 0.9500 . ?
C32A C33A 1.381(3) . ?
C32A H32A 0.9500 . ?
C33A C34A 1.384(3) . ?
C33A H33A 0.9500 . ?
C34A H34A 0.9500 . ?
P1B O2B 1.4711(15) . ?
P1B O3B 1.5622(15) . ?
P1B O6B 1.5629(14) . ?
P1B C9B 1.8232(19) . ?
O3B C4B 1.458(3) . ?
C4B C5B 1.390(4) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
C5B H5B1 0.9800 . ?
C5B H5B2 0.9800 . ?
C5B H5B3 0.9800 . ?
O6B C7B 1.458(2) . ?
C7B C8B 1.486(3) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C9B N10B 1.462(2) . ?
C9B C21B 1.531(3) . ?
C9B H9B 1.0000 . ?
N10B S11B 1.6131(17) . ?
N10B H10B 0.78(2) . ?
S11B O12B 1.4325(16) . ?
S11B O13B 1.4343(16) . ?
S11B C14B 1.7655(19) . ?
C14B C19B 1.382(3) . ?
C14B C15B 1.386(3) . ?
C15B C16B 1.383(3) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.389(3) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.381(3) . ?
C17B C20B 1.509(3) . ?
C18B C19B 1.383(3) . ?
C18B H18B 0.9500 . ?
C19B H19B 0.9500 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C21B N22B 1.460(2) . ?
C21B C23B 1.488(3) . ?
C21B H21B 1.0000 . ?
N22B C23B 1.459(2) . ?
N22B C28B 1.470(2) . ?
C23B C24B 1.486(3) . ?
C23B H23B 1.0000 . ?
C24B F27B 1.330(3) . ?
C24B F25B 1.337(2) . ?
C24B F26B 1.347(2) . ?
C28B C29B 1.511(3) . ?
C28B H28C 0.9900 . ?
C28B H28D 0.9900 . ?
C29B C30B 1.386(3) . ?
C29B C34B 1.393(3) . ?
C30B C31B 1.389(3) . ?
C30B H30B 0.9500 . ?
C31B C32B 1.382(3) . ?
C31B H31B 0.9500 . ?
C32B C33B 1.379(3) . ?
C32B H32B 0.9500 . ?
C33B C34B 1.387(3) . ?
C33B H33B 0.9500 . ?
C34B H34B 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
O2A P1A O6A 114.04(7) . . ?
O2A P1A O3A 116.32(8) . . ?
O6A P1A O3A 104.32(8) . . ?
O2A P1A C9A 113.91(8) . . ?
O6A P1A C9A 106.44(8) . . ?
O3A P1A C9A 100.35(8) . . ?
C4A O3A P1A 119.54(13) . . ?
C5A C4A O3A 109.93(19) . . ?
C5A C4A H4A1 109.7 . . ?
O3A C4A H4A1 109.7 . . ?
C5A C4A H4A2 109.7 . . ?
O3A C4A H4A2 109.7 . . ?
H4A1 C4A H4A2 108.2 . . ?
C4A C5A H5A1 109.5 . . ?
C4A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
C4A C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
C7A O6A P1A 122.83(12) . . ?
O6A C7A C8A 108.89(16) . . ?
O6A C7A H7A1 109.9 . . ?
C8A C7A H7A1 109.9 . . ?
O6A C7A H7A2 109.9 . . ?
C8A C7A H7A2 109.9 . . ?
H7A1 C7A H7A2 108.3 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
N10A C9A C21A 107.88(15) . . ?
N10A C9A P1A 111.52(12) . . ?
C21A C9A P1A 109.97(12) . . ?
N10A C9A H9A 109.1 . . ?
C21A C9A H9A 109.1 . . ?
P1A C9A H9A 109.1 . . ?
C9A N10A S11A 122.36(13) . . ?
C9A N10A H10A 121.0(17) . . ?
S11A N10A H10A 112.7(17) . . ?
O12A S11A O13A 120.11(8) . . ?
O12A S11A N10A 107.61(8) . . ?
O13A S11A N10A 106.09(8) . . ?
O12A S11A C14A 108.24(9) . . ?
O13A S11A C14A 105.52(8) . . ?
N10A S11A C14A 108.90(8) . . ?
C15A C14A C19A 120.54(18) . . ?
C15A C14A S11A 121.18(15) . . ?
C19A C14A S11A 118.19(14) . . ?
C14A C15A C16A 119.16(19) . . ?
C14A C15A H15A 120.4 . . ?
C16A C15A H15A 120.4 . . ?
C17A C16A C15A 121.35(19) . . ?
C17A C16A H16A 119.3 . . ?
C15A C16A H16A 119.3 . . ?
C16A C17A C18A 118.43(18) . . ?
C16A C17A C20A 121.73(19) . . ?
C18A C17A C20A 119.82(19) . . ?
C19A C18A C17A 120.98(19) . . ?
C19A C18A H18A 119.5 . . ?
C17A C18A H18A 119.5 . . ?
C18A C19A C14A 119.47(18) . . ?
C18A C19A H19A 120.3 . . ?
C14A C19A H19A 120.3 . . ?
C17A C20A H20A 109.5 . . ?
C17A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C17A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
N22A C21A C23A 59.35(11) . . ?
N22A C21A C9A 119.44(15) . . ?
C23A C21A C9A 127.99(16) . . ?
N22A C21A H21A 113.1 . . ?
C23A C21A H21A 113.1 . . ?
C9A C21A H21A 113.1 . . ?
C21A N22A C23A 61.32(12) . . ?
C21A N22A C28A 114.54(15) . . ?
C23A N22A C28A 115.48(15) . . ?
N22A C23A C24A 116.21(16) . . ?
N22A C23A C21A 59.33(11) . . ?
C24A C23A C21A 124.51(16) . . ?
N22A C23A H23A 115.0 . . ?
C24A C23A H23A 115.0 . . ?
C21A C23A H23A 115.0 . . ?
F25A C24A F27A 106.44(18) . . ?
F25A C24A F26A 106.75(17) . . ?
F27A C24A F26A 106.30(17) . . ?
F25A C24A C23A 114.57(16) . . ?
F27A C24A C23A 111.20(17) . . ?
F26A C24A C23A 111.11(18) . . ?
N22A C28A C29A 110.64(15) . . ?
N22A C28A H28A 109.5 . . ?
C29A C28A H28A 109.5 . . ?
N22A C28A H28B 109.5 . . ?
C29A C28A H28B 109.5 . . ?
H28A C28A H28B 108.1 . . ?
C30A C29A C34A 118.11(18) . . ?
C30A C29A C28A 120.30(18) . . ?
C34A C29A C28A 121.58(18) . . ?
C29A C30A C31A 121.00(19) . . ?
C29A C30A H30A 119.5 . . ?
C31A C30A H30A 119.5 . . ?
C32A C31A C30A 120.5(2) . . ?
C32A C31A H31A 119.8 . . ?
C30A C31A H31A 119.8 . . ?
C31A C32A C33A 119.1(2) . . ?
C31A C32A H32A 120.4 . . ?
C33A C32A H32A 120.4 . . ?
C32A C33A C34A 120.4(2) . . ?
C32A C33A H33A 119.8 . . ?
C34A C33A H33A 119.8 . . ?
C33A C34A C29A 120.93(19) . . ?
C33A C34A H34A 119.5 . . ?
C29A C34A H34A 119.5 . . ?
O2B P1B O3B 114.04(8) . . ?
O2B P1B O6B 116.32(9) . . ?
O3B P1B O6B 104.47(9) . . ?
O2B P1B C9B 113.25(9) . . ?
O3B P1B C9B 107.60(9) . . ?
O6B P1B C9B 99.79(8) . . ?
C4B O3B P1B 121.52(15) . . ?
C5B C4B O3B 111.2(3) . . ?
C5B C4B H4B1 109.4 . . ?
O3B C4B H4B1 109.4 . . ?
C5B C4B H4B2 109.4 . . ?
O3B C4B H4B2 109.4 . . ?
H4B1 C4B H4B2 108.0 . . ?
C4B C5B H5B1 109.5 . . ?
C4B C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
C4B C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
C7B O6B P1B 119.81(13) . . ?
O6B C7B C8B 107.60(17) . . ?
O6B C7B H7B1 110.2 . . ?
C8B C7B H7B1 110.2 . . ?
O6B C7B H7B2 110.2 . . ?
C8B C7B H7B2 110.2 . . ?
H7B1 C7B H7B2 108.5 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
N10B C9B C21B 107.95(16) . . ?
N10B C9B P1B 110.66(13) . . ?
C21B C9B P1B 109.83(13) . . ?
N10B C9B H9B 109.5 . . ?
C21B C9B H9B 109.5 . . ?
P1B C9B H9B 109.5 . . ?
C9B N10B S11B 122.20(15) . . ?
C9B N10B H10B 120.7(16) . . ?
S11B N10B H10B 112.5(16) . . ?
O12B S11B O13B 120.51(10) . . ?
O12B S11B N10B 106.48(9) . . ?
O13B S11B N10B 106.78(9) . . ?
O12B S11B C14B 106.21(9) . . ?
O13B S11B C14B 107.74(10) . . ?
N10B S11B C14B 108.73(9) . . ?
C19B C14B C15B 120.29(19) . . ?
C19B C14B S11B 120.68(16) . . ?
C15B C14B S11B 119.03(16) . . ?
C16B C15B C14B 119.4(2) . . ?
C16B C15B H15B 120.3 . . ?
C14B C15B H15B 120.3 . . ?
C15B C16B C17B 121.3(2) . . ?
C15B C16B H16B 119.4 . . ?
C17B C16B H16B 119.4 . . ?
C18B C17B C16B 118.03(19) . . ?
C18B C17B C20B 121.0(2) . . ?
C16B C17B C20B 120.9(2) . . ?
C17B C18B C19B 121.7(2) . . ?
C17B C18B H18B 119.1 . . ?
C19B C18B H18B 119.1 . . ?
C14B C19B C18B 119.2(2) . . ?
C14B C19B H19B 120.4 . . ?
C18B C19B H19B 120.4 . . ?
C17B C20B H20D 109.5 . . ?
C17B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C17B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
N22B C21B C23B 59.33(12) . . ?
N22B C21B C9B 119.21(16) . . ?
C23B C21B C9B 127.05(18) . . ?
N22B C21B H21B 113.4 . . ?
C23B C21B H21B 113.4 . . ?
C9B C21B H21B 113.4 . . ?
C23B N22B C21B 61.30(12) . . ?
C23B N22B C28B 116.63(16) . . ?
C21B N22B C28B 114.76(16) . . ?
N22B C23B C24B 116.24(17) . . ?
N22B C23B C21B 59.37(12) . . ?
C24B C23B C21B 124.47(18) . . ?
N22B C23B H23B 115.0 . . ?
C24B C23B H23B 115.0 . . ?
C21B C23B H23B 115.0 . . ?
F27B C24B F25B 106.94(19) . . ?
F27B C24B F26B 106.10(19) . . ?
F25B C24B F26B 106.58(18) . . ?
F27B C24B C23B 114.35(17) . . ?
F25B C24B C23B 111.40(19) . . ?
F26B C24B C23B 111.02(18) . . ?
N22B C28B C29B 112.49(16) . . ?
N22B C28B H28C 109.1 . . ?
C29B C28B H28C 109.1 . . ?
N22B C28B H28D 109.1 . . ?
C29B C28B H28D 109.1 . . ?
H28C C28B H28D 107.8 . . ?
C30B C29B C34B 118.41(18) . . ?
C30B C29B C28B 122.52(17) . . ?
C34B C29B C28B 119.07(18) . . ?
C29B C30B C31B 120.54(19) . . ?
C29B C30B H30B 119.7 . . ?
C31B C30B H30B 119.7 . . ?
C32B C31B C30B 120.6(2) . . ?
C32B C31B H31B 119.7 . . ?
C30B C31B H31B 119.7 . . ?
C33B C32B C31B 119.24(19) . . ?
C33B C32B H32B 120.4 . . ?
C31B C32B H32B 120.4 . . ?
C32B C33B C34B 120.3(2) . . ?
C32B C33B H33B 119.9 . . ?
C34B C33B H33B 119.9 . . ?
C33B C34B C29B 120.9(2) . . ?
C33B C34B H34B 119.6 . . ?
C29B C34B H34B 119.6 . . ?

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
O2A P1A O3A C4A 64.29(19) . . . . ?
O6A P1A O3A C4A -62.25(18) . . . . ?
C9A P1A O3A C4A -172.34(17) . . . . ?
P1A O3A C4A C5A 169.73(19) . . . . ?
O2A P1A O6A C7A 4.65(17) . . . . ?
O3A P1A O6A C7A 132.60(14) . . . . ?
C9A P1A O6A C7A -121.82(15) . . . . ?
P1A O6A C7A C8A 142.10(15) . . . . ?
O2A P1A C9A N10A 75.17(14) . . . . ?
O6A P1A C9A N10A -158.28(12) . . . . ?
O3A P1A C9A N10A -49.86(14) . . . . ?
O2A P1A C9A C21A -44.46(15) . . . . ?
O6A P1A C9A C21A 82.09(13) . . . . ?
O3A P1A C9A C21A -169.49(12) . . . . ?
C21A C9A N10A S11A -114.25(15) . . . . ?
P1A C9A N10A S11A 124.89(12) . . . . ?
C9A N10A S11A O12A 28.74(16) . . . . ?
C9A N10A S11A O13A 158.49(14) . . . . ?
C9A N10A S11A C14A -88.37(15) . . . . ?
O12A S11A C14A C15A -5.59(18) . . . . ?
O13A S11A C14A C15A -135.35(16) . . . . ?
N10A S11A C14A C15A 111.13(16) . . . . ?
O12A S11A C14A C19A 170.94(14) . . . . ?
O13A S11A C14A C19A 41.18(16) . . . . ?
N10A S11A C14A C19A -72.34(16) . . . . ?
C19A C14A C15A C16A -1.8(3) . . . . ?
S11A C14A C15A C16A 174.63(15) . . . . ?
C14A C15A C16A C17A -0.8(3) . . . . ?
C15A C16A C17A C18A 2.6(3) . . . . ?
C15A C16A C17A C20A -175.62(19) . . . . ?
C16A C17A C18A C19A -2.0(3) . . . . ?
C20A C17A C18A C19A 176.31(19) . . . . ?
C17A C18A C19A C14A -0.5(3) . . . . ?
C15A C14A C19A C18A 2.5(3) . . . . ?
S11A C14A C19A C18A -174.10(15) . . . . ?
N10A C9A C21A N22A -160.33(15) . . . . ?
P1A C9A C21A N22A -38.5(2) . . . . ?
N10A C9A C21A C23A 127.25(19) . . . . ?
P1A C9A C21A C23A -110.92(19) . . . . ?
C9A C21A N22A C23A -119.15(19) . . . . ?
C23A C21A N22A C28A -106.82(17) . . . . ?
C9A C21A N22A C28A 134.03(17) . . . . ?
C21A N22A C23A C24A 116.25(19) . . . . ?
C28A N22A C23A C24A -138.46(17) . . . . ?
C28A N22A C23A C21A 105.29(17) . . . . ?
C9A C21A C23A N22A 105.2(2) . . . . ?
N22A C21A C23A C24A -102.4(2) . . . . ?
C9A C21A C23A C24A 2.8(3) . . . . ?
N22A C23A C24A F25A -40.1(2) . . . . ?
C21A C23A C24A F25A 29.3(3) . . . . ?
N22A C23A C24A F27A 80.7(2) . . . . ?
C21A C23A C24A F27A 150.07(18) . . . . ?
N22A C23A C24A F26A -161.16(16) . . . . ?
C21A C23A C24A F26A -91.7(2) . . . . ?
C21A N22A C28A C29A 158.53(16) . . . . ?
C23A N22A C28A C29A 90.0(2) . . . . ?
N22A C28A C29A C30A -96.9(2) . . . . ?
N22A C28A C29A C34A 82.3(2) . . . . ?
C34A C29A C30A C31A -0.9(3) . . . . ?
C28A C29A C30A C31A 178.3(2) . . . . ?
C29A C30A C31A C32A 0.4(4) . . . . ?
C30A C31A C32A C33A 0.3(4) . . . . ?
C31A C32A C33A C34A -0.4(4) . . . . ?
C32A C33A C34A C29A -0.2(4) . . . . ?
C30A C29A C34A C33A 0.8(3) . . . . ?
C28A C29A C34A C33A -178.3(2) . . . . ?
O2B P1B O3B C4B -6.8(2) . . . . ?
O6B P1B O3B C4B -134.87(17) . . . . ?
C9B P1B O3B C4B 119.70(17) . . . . ?
P1B O3B C4B C5B 175.9(3) . . . . ?
O2B P1B O6B C7B -59.56(19) . . . . ?
O3B P1B O6B C7B 67.10(18) . . . . ?
C9B P1B O6B C7B 178.28(16) . . . . ?
P1B O6B C7B C8B 172.30(16) . . . . ?
O2B P1B C9B N10B -73.14(15) . . . . ?
O3B P1B C9B N10B 159.89(13) . . . . ?
O6B P1B C9B N10B 51.18(15) . . . . ?
O2B P1B C9B C21B 45.95(16) . . . . ?
O3B P1B C9B C21B -81.02(15) . . . . ?
O6B P1B C9B C21B 170.27(14) . . . . ?
C21B C9B N10B S11B 113.32(16) . . . . ?
P1B C9B N10B S11B -126.46(13) . . . . ?
C9B N10B S11B O12B -155.30(15) . . . . ?
C9B N10B S11B O13B -25.35(18) . . . . ?
C9B N10B S11B C14B 90.64(16) . . . . ?
O12B S11B C14B C19B 149.61(16) . . . . ?
O13B S11B C14B C19B 19.21(19) . . . . ?
N10B S11B C14B C19B -96.16(18) . . . . ?
O12B S11B C14B C15B -29.85(18) . . . . ?
O13B S11B C14B C15B -160.25(16) . . . . ?
N10B S11B C14B C15B 84.39(17) . . . . ?
C19B C14B C15B C16B -2.3(3) . . . . ?
S11B C14B C15B C16B 177.20(16) . . . . ?
C14B C15B C16B C17B 0.9(3) . . . . ?
C15B C16B C17B C18B 1.1(3) . . . . ?
C15B C16B C17B C20B -178.8(2) . . . . ?
C16B C17B C18B C19B -1.9(3) . . . . ?
C20B C17B C18B C19B 178.0(2) . . . . ?
C15B C14B C19B C18B 1.5(3) . . . . ?
S11B C14B C19B C18B -177.93(16) . . . . ?
C17B C18B C19B C14B 0.6(3) . . . . ?
N10B C9B C21B N22B 162.71(16) . . . . ?
P1B C9B C21B N22B 42.0(2) . . . . ?
N10B C9B C21B C23B -125.4(2) . . . . ?
P1B C9B C21B C23B 113.89(19) . . . . ?
C9B C21B N22B C23B 118.1(2) . . . . ?
C23B C21B N22B C28B 108.07(18) . . . . ?
C9B C21B N22B C28B -133.83(18) . . . . ?
C21B N22B C23B C24B -116.2(2) . . . . ?
C28B N22B C23B C24B 138.75(18) . . . . ?
C28B N22B C23B C21B -105.05(18) . . . . ?
C9B C21B C23B N22B -105.3(2) . . . . ?
N22B C21B C23B C24B 102.5(2) . . . . ?
C9B C21B C23B C24B -2.8(3) . . . . ?
N22B C23B C24B F27B 35.0(3) . . . . ?
C21B C23B C24B F27B -34.5(3) . . . . ?
N22B C23B C24B F25B 156.37(17) . . . . ?
C21B C23B C24B F25B 86.9(2) . . . . ?
N22B C23B C24B F26B -85.0(2) . . . . ?
C21B C23B C24B F26B -154.49(19) . . . . ?
C23B N22B C28B C29B -93.1(2) . . . . ?
C21B N22B C28B C29B -162.01(16) . . . . ?
N22B C28B C29B C30B -15.7(3) . . . . ?
N22B C28B C29B C34B 164.44(18) . . . . ?
C34B C29B C30B C31B -0.2(3) . . . . ?
C28B C29B C30B C31B -179.98(18) . . . . ?
C29B C30B C31B C32B -0.2(3) . . . . ?
C30B C31B C32B C33B 0.4(3) . . . . ?
C31B C32B C33B C34B -0.2(3) . . . . ?
C32B C33B C34B C29B -0.2(3) . . . . ?
C30B C29B C34B C33B 0.3(3) . . . . ?
C28B C29B C34B C33B -179.83(19) . . . . ?

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
C9A H9A F25A 1.00 2.35 2.993(2) 121.2 .
N10A H10A O2A 0.80(2) 1.99(2) 2.783(2) 175(2) 2_765
C23A H23A O13A 1.00 2.33 3.284(2) 159.6 2_665
C4B H4B1 N22B 0.99 2.61 3.311(3) 127.6 .
C8B H8B2 O13B 0.98 2.55 3.470(3) 155.7 1_455
C9B H9B F27B 1.00 2.37 3.016(2) 121.4 .
N10B H10B O2B 0.78(2) 2.02(2) 2.800(2) 173(2) 2_576
C23B H23B O12B 1.00 2.44 3.359(3) 152.4 2_676

_refine_diff_density_max         0.552
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.057

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_38
_database_code_depnum_ccdc_archive 'CCDC 1568458'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2018-03-14 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         'C16 H21 F3 N O6 P'
_chemical_formula_sum            'C16 H21 F3 N O6 P'
_chemical_formula_weight         411.31

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'
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                   10.1589(16)
_cell_length_b                   10.3309(11)
_cell_length_c                   10.8732(11)
_cell_angle_alpha                108.225(10)
_cell_angle_beta                 112.480(12)
_cell_angle_gamma                90.483(10)
_cell_volume                     990.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    1078
_cell_measurement_theta_min      3.4980
_cell_measurement_theta_max      24.0030

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.197
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.91606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_measurement_method       '/w scan'
_diffrn_reflns_number            6885
_diffrn_reflns_av_unetI/netI     0.1084
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.643
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3461
_reflns_number_gt                1499
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.1893P)²+0.2757P] 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         3461
_refine_ls_number_parameters     246
_refine_ls_number_restraints     140
_refine_ls_R_factor_all          0.2218
_refine_ls_R_factor_gt           0.1181
_refine_ls_wR_factor_ref         0.3662
_refine_ls_wR_factor_gt          0.3060
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.080
_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 0.7084(3) 0.2891(2) 0.4446(2) 0.0740(8) Uani 1 1 d . . . . .
O2 O 0.6427(6) 0.3374(5) 0.5455(5) 0.0826(17) Uani 1 1 d . . . . .
O3 O 0.8739(7) 0.3195(8) 0.5102(7) 0.119(2) Uani 1 1 d . . . . .
C4 C 0.9709(15) 0.3508(13) 0.6695(15) 0.150(5) Uani 1 1 d D . . . .
H4B H 0.9213 0.3170 0.7186 0.180 Uiso 1 1 calc R U . . .
H4A H 1.0633 0.3141 0.6842 0.180 Uiso 1 1 calc R U . . .
C5 C 0.9891(16) 0.5018(14) 0.711(2) 0.199(8) Uani 1 1 d D . . . .
H5C H 1.0233 0.5294 0.6484 0.299 Uiso 1 1 calc R U . . .
H5B H 1.0596 0.5427 0.8090 0.299 Uiso 1 1 calc R U . . .
H5A H 0.8965 0.5339 0.7021 0.299 Uiso 1 1 calc R U . . .
O6 O 0.6724(6) 0.1331(5) 0.3545(5) 0.0788(16) Uani 1 1 d . . . . .
C7 C 0.6961(12) 0.0306(9) 0.4263(10) 0.108(3) Uani 1 1 d D . . . .
H7B H 0.6282 0.0338 0.4722 0.130 Uiso 1 1 calc R U . . .
H7A H 0.7955 0.0507 0.5002 0.130 Uiso 1 1 calc R U . . .
C8 C 0.6724(14) -0.1099(10) 0.3171(11) 0.146(5) Uani 1 1 d D . . . .
H8C H 0.6231 -0.1047 0.2220 0.219 Uiso 1 1 calc R U . . .
H8B H 0.6132 -0.1749 0.3308 0.219 Uiso 1 1 calc R U . . .
H8A H 0.7655 -0.1414 0.3273 0.219 Uiso 1 1 calc R U . . .
C9 C 0.6511(9) 0.3650(8) 0.3090(7) 0.074(2) Uani 1 1 d . . . . .
H9 H 0.6677 0.3193 0.2215 0.089 Uiso 1 1 calc R U . . .
O10 O 0.6756(8) 0.5167(6) 0.3662(6) 0.0917(18) Uani 1 1 d . . . . .
C11 C 0.5301(10) 0.4440(7) 0.2959(7) 0.063(2) Uani 1 1 d . . . . .
H11 H 0.4806 0.4428 0.3594 0.076 Uiso 1 1 calc R U . . .
C12 C 0.4427(9) 0.4671(8) 0.1661(8) 0.071(2) Uani 1 1 d . . . . .
H12 H 0.5044 0.4792 0.1165 0.085 Uiso 1 1 calc R U . . .
C13 C 0.3255(13) 0.3388(10) 0.0704(10) 0.093(3) Uani 1 1 d . . . . .
F14 F 0.2428(7) 0.3500(6) -0.0548(6) 0.137(2) Uani 1 1 d . . . . .
F15 F 0.2339(7) 0.3272(6) 0.1310(7) 0.126(2) Uani 1 1 d . . . . .
F16 F 0.3823(7) 0.2226(5) 0.0473(5) 0.1106(18) Uani 1 1 d . . . . .
N17 N 0.3726(7) 0.5843(6) 0.1921(6) 0.0682(17) Uani 1 1 d . U . . .
H17 H 0.3523 0.6083 0.2672 0.082 Uiso 1 1 calc R U . . .
C18 C 0.3350(9) 0.6619(8) 0.1055(8) 0.078(2) Uani 1 1 d . U . . .
O19 O 0.3552(7) 0.6427(5) 0.0008(5) 0.0846(17) Uani 1 1 d . U . . .
O20 O 0.2751(7) 0.7673(5) 0.1618(5) 0.0914(18) Uani 1 1 d . U . . .
C21 C 0.2281(11) 0.8617(8) 0.0823(9) 0.090(3) Uani 1 1 d . U . . .
H21B H 0.1507 0.8133 -0.0124 0.108 Uiso 1 1 calc R U . . .
H21A H 0.3095 0.9012 0.0701 0.108 Uiso 1 1 calc R U . . .
C22 C 0.1742(10) 0.9713(8) 0.1686(8) 0.068(2) Uani 1 1 d . U . . .
C23 C 0.2662(11) 1.0888(10) 0.2639(10) 0.091(3) Uani 1 1 d . U . . .
H23 H 0.3603 1.0983 0.2662 0.109 Uiso 1 1 calc R U . . .
C24 C 0.2342(15) 1.1904(12) 0.3532(12) 0.118(3) Uani 1 1 d . U . . .
H24 H 0.3043 1.2677 0.4195 0.142 Uiso 1 1 calc R U . . .
C25 C 0.1076(15) 1.1815(11) 0.3478(12) 0.108(3) Uani 1 1 d . U . . .
H25 H 0.0871 1.2543 0.4137 0.129 Uiso 1 1 calc R U . . .
C26 C 0.0024(12) 1.0813(13) 0.2598(11) 0.103(3) Uani 1 1 d . U . . .
H26 H -0.0915 1.0849 0.2586 0.124 Uiso 1 1 calc R U . . .
C27 C 0.0346(12) 0.9594(11) 0.1598(11) 0.107(3) Uani 1 1 d . U . . .
H27 H -0.0353 0.8811 0.0962 0.129 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 O2 1.457(4) . ?
P1 O3 1.538(7) . ?
P1 O6 1.555(5) . ?
P1 C9 1.789(7) . ?
O3 C4 1.555(14) . ?
C4 C5 1.471(9) . ?
C4 H4B 0.9900 . ?
C4 H4A 0.9900 . ?
C5 H5C 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5A 0.9800 . ?
O6 C7 1.472(9) . ?
C7 C8 1.507(8) . ?
C7 H7B 0.9900 . ?
C7 H7A 0.9900 . ?
C8 H8C 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8A 0.9800 . ?
C9 C11 1.467(10) . ?
C9 O10 1.473(8) . ?
C9 H9 1.0000 . ?
O10 C11 1.446(9) . ?
C11 C12 1.447(9) . ?
C11 H11 1.0000 . ?
C12 N17 1.417(8) . ?
C12 C13 1.556(12) . ?
C12 H12 1.0000 . ?
C13 F16 1.332(9) . ?
C13 F14 1.341(10) . ?
C13 F15 1.353(10) . ?
N17 C18 1.370(9) . ?
N17 H17 0.8800 . ?
C18 O19 1.190(8) . ?
C18 O20 1.345(8) . ?
O20 C21 1.465(9) . ?
C21 C22 1.483(10) . ?
C21 H21B 0.9900 . ?
C21 H21A 0.9900 . ?
C22 C23 1.369(11) . ?
C22 C27 1.386(12) . ?
C23 C24 1.327(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.265(13) . ?
C24 H24 0.9500 . ?
C25 C26 1.307(13) . ?
C25 H25 0.9500 . ?
C26 C27 1.516(14) . ?
C26 H26 0.9500 . ?
C27 H27 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
O2 P1 O3 114.5(3) . . ?
O2 P1 O6 117.1(3) . . ?
O3 P1 O6 104.8(4) . . ?
O2 P1 C9 112.6(3) . . ?
O3 P1 C9 105.1(4) . . ?
O6 P1 C9 101.2(3) . . ?
P1 O3 C4 124.7(7) . . ?
C5 C4 O3 96.7(12) . . ?
C5 C4 H4B 112.4 . . ?
O3 C4 H4B 112.4 . . ?
C5 C4 H4A 112.4 . . ?
O3 C4 H4A 112.4 . . ?
H4B C4 H4A 110.0 . . ?
C4 C5 H5C 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5C C5 H5B 109.5 . . ?
C4 C5 H5A 109.5 . . ?
H5C C5 H5A 109.5 . . ?
H5B C5 H5A 109.5 . . ?
C7 O6 P1 119.4(5) . . ?
O6 C7 C8 108.3(7) . . ?
O6 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
O6 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
H7B C7 H7A 108.4 . . ?
C7 C8 H8C 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8C C8 H8B 109.5 . . ?
C7 C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
H8B C8 H8A 109.5 . . ?
C11 C9 O10 58.9(4) . . ?
C11 C9 P1 118.8(5) . . ?
O10 C9 P1 112.8(5) . . ?
C11 C9 H9 117.6 . . ?
O10 C9 H9 117.6 . . ?
P1 C9 H9 117.6 . . ?
C11 O10 C9 60.3(5) . . ?
O10 C11 C12 114.8(6) . . ?
O10 C11 C9 60.7(5) . . ?
C12 C11 C9 122.9(6) . . ?
O10 C11 H11 115.6 . . ?
C12 C11 H11 115.6 . . ?
C9 C11 H11 115.6 . . ?
N17 C12 C11 111.7(6) . . ?
N17 C12 C13 108.2(7) . . ?
C11 C12 C13 108.1(6) . . ?
N17 C12 H12 109.6 . . ?
C11 C12 H12 109.6 . . ?
C13 C12 H12 109.6 . . ?
F16 C13 F14 108.7(7) . . ?
F16 C13 F15 108.3(8) . . ?
F14 C13 F15 105.2(9) . . ?
F16 C13 C12 112.1(9) . . ?
F14 C13 C12 111.8(7) . . ?
F15 C13 C12 110.4(7) . . ?
C18 N17 C12 122.9(5) . . ?
C18 N17 H17 118.5 . . ?
C12 N17 H17 118.5 . . ?
O19 C18 O20 125.4(7) . . ?
O19 C18 N17 126.4(7) . . ?
O20 C18 N17 108.2(6) . . ?
C18 O20 C21 115.6(5) . . ?
O20 C21 C22 105.3(6) . . ?
O20 C21 H21B 110.7 . . ?
C22 C21 H21B 110.7 . . ?
O20 C21 H21A 110.7 . . ?
C22 C21 H21A 110.7 . . ?
H21B C21 H21A 108.8 . . ?
C23 C22 C27 117.8(8) . . ?
C23 C22 C21 119.2(9) . . ?
C27 C22 C21 123.0(9) . . ?
C24 C23 C22 125.1(10) . . ?
C24 C23 H23 117.5 . . ?
C22 C23 H23 117.5 . . ?
C25 C24 C23 118.2(13) . . ?
C25 C24 H24 120.9 . . ?
C23 C24 H24 120.9 . . ?
C24 C25 C26 126.1(12) . . ?
C24 C25 H25 117.0 . . ?
C26 C25 H25 117.0 . . ?
C25 C26 C27 118.0(10) . . ?
C25 C26 H26 121.0 . . ?
C27 C26 H26 121.0 . . ?
C22 C27 C26 114.7(9) . . ?
C22 C27 H27 122.7 . . ?
C26 C27 H27 122.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 P1 O3 C4 20.6(10) . . . . ?
O6 P1 O3 C4 -109.1(8) . . . . ?
C9 P1 O3 C4 144.7(8) . . . . ?
P1 O3 C4 C5 -96.8(11) . . . . ?
O2 P1 O6 C7 -53.9(7) . . . . ?
O3 P1 O6 C7 74.2(7) . . . . ?
C9 P1 O6 C7 -176.7(6) . . . . ?
P1 O6 C7 C8 -172.3(7) . . . . ?
O2 P1 C9 C11 -10.8(8) . . . . ?
O3 P1 C9 C11 -136.1(7) . . . . ?
O6 P1 C9 C11 115.0(7) . . . . ?
O2 P1 C9 O10 55.1(6) . . . . ?
O3 P1 C9 O10 -70.2(6) . . . . ?
O6 P1 C9 O10 -179.1(5) . . . . ?
P1 C9 O10 C11 -110.9(5) . . . . ?
C9 O10 C11 C12 -115.3(6) . . . . ?
P1 C9 C11 O10 100.7(6) . . . . ?
O10 C9 C11 C12 102.1(8) . . . . ?
P1 C9 C11 C12 -157.2(7) . . . . ?
O10 C11 C12 N17 -87.6(8) . . . . ?
C9 C11 C12 N17 -157.6(7) . . . . ?
O10 C11 C12 C13 153.4(6) . . . . ?
C9 C11 C12 C13 83.5(10) . . . . ?
N17 C12 C13 F16 -176.5(6) . . . . ?
C11 C12 C13 F16 -55.4(9) . . . . ?
N17 C12 C13 F14 61.2(9) . . . . ?
C11 C12 C13 F14 -177.7(7) . . . . ?
N17 C12 C13 F15 -55.7(8) . . . . ?
C11 C12 C13 F15 65.5(9) . . . . ?
C11 C12 N17 C18 152.1(8) . . . . ?
C13 C12 N17 C18 -89.1(9) . . . . ?
C12 N17 C18 O19 0.0(14) . . . . ?
C12 N17 C18 O20 -178.0(7) . . . . ?
O19 C18 O20 C21 2.0(13) . . . . ?
N17 C18 O20 C21 180.0(7) . . . . ?
C18 O20 C21 C22 -177.0(8) . . . . ?
O20 C21 C22 C23 93.1(8) . . . . ?
O20 C21 C22 C27 -85.5(9) . . . . ?
C27 C22 C23 C24 3.0(13) . . . . ?
C21 C22 C23 C24 -175.7(8) . . . . ?
C22 C23 C24 C25 -2.6(16) . . . . ?
C23 C24 C25 C26 -1.1(18) . . . . ?
C24 C25 C26 C27 3.8(16) . . . . ?
C23 C22 C27 C26 -0.1(11) . . . . ?
C21 C22 C27 C26 178.5(7) . . . . ?
C25 C26 C27 C22 -3.0(13) . . . . ?

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
C9 H9 O19 1.00 2.49 3.320(8) 139.8 2_665
C12 H12 O19 1.00 2.38 3.224(8) 141.7 2_665
N17 H17 O2 0.88 1.92 2.778(6) 166.1 2_666

_refine_diff_density_max         0.713
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.093

