# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1575309'
_audit_update_record             
;
2017-09-19 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H37 Cl3 O6'
_chemical_formula_weight         587.93

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

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

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

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

_cell_length_a                   17.6945(11)
_cell_length_b                   11.4264(7)
_cell_length_c                   14.1947(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.3820(10)
_cell_angle_gamma                90
_cell_volume                     2846.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9117
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25.78

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.363
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8932
_exptl_absorpt_correction_T_max  0.9563
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            25518
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.160
_diffrn_reflns_theta_max         26.114
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             5275
_reflns_number_gt                4573
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0367P)²+1.8207P] 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         5275
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C1 C 0.72638(8) 0.40734(13) 0.54672(10) 0.0134(3) Uani 1 1 d . . . . .
C2 C 0.65477(8) 0.39962(13) 0.47185(11) 0.0134(3) Uani 1 1 d . . . . .
H2A H 0.633495 0.479086 0.459481 0.016 Uiso 1 1 calc R U . . .
H2AB H 0.669613 0.369069 0.411600 0.016 Uiso 1 1 calc R U . . .
C3 C 0.59301(8) 0.31975(13) 0.50453(10) 0.0136(3) Uani 1 1 d . . . . .
C4 C 0.62826(9) 0.19710(14) 0.52391(11) 0.0151(3) Uani 1 1 d . . . . .
H4A H 0.589593 0.143736 0.544818 0.018 Uiso 1 1 calc R U . . .
H4AB H 0.644044 0.165266 0.464580 0.018 Uiso 1 1 calc R U . . .
C5 C 0.69775(9) 0.20295(14) 0.60097(11) 0.0173(3) Uani 1 1 d . . . . .
H5 H 0.719235 0.122623 0.613141 0.021 Uiso 1 1 calc R U . . .
C6 C 0.75835(8) 0.28267(14) 0.56644(11) 0.0154(3) Uani 1 1 d . . . . .
H6A H 0.774525 0.249926 0.507636 0.019 Uiso 1 1 calc R U . . .
H6AB H 0.803555 0.286100 0.615313 0.019 Uiso 1 1 calc R U . . .
C7 C 0.57088(9) 0.36923(15) 0.59866(11) 0.0163(3) Uani 1 1 d . . . . .
H7A H 0.548759 0.448380 0.587591 0.020 Uiso 1 1 calc R U . . .
H7AB H 0.531887 0.318306 0.621740 0.020 Uiso 1 1 calc R U . . .
C8 C 0.64121(9) 0.37567(15) 0.67386(11) 0.0178(3) Uani 1 1 d . . . . .
H8 H 0.625976 0.408234 0.734040 0.021 Uiso 1 1 calc R U . . .
C9 C 0.70156(9) 0.45539(14) 0.63918(11) 0.0167(3) Uani 1 1 d . . . . .
H9A H 0.746351 0.460464 0.688567 0.020 Uiso 1 1 calc R U . . .
H9AB H 0.680463 0.535155 0.627984 0.020 Uiso 1 1 calc R U . . .
C10 C 0.67389(9) 0.25276(15) 0.69281(11) 0.0201(4) Uani 1 1 d . . . . .
H10A H 0.635029 0.201431 0.715736 0.024 Uiso 1 1 calc R U . . .
H10B H 0.718545 0.256106 0.742503 0.024 Uiso 1 1 calc R U . . .
C11 C 0.78649(8) 0.48444(13) 0.50849(11) 0.0141(3) Uani 1 1 d . . . . .
C12 C 0.81234(9) 0.58815(14) 0.55317(11) 0.0156(3) Uani 1 1 d . . . . .
H12 H 0.792695 0.612588 0.609201 0.019 Uiso 1 1 calc R U . . .
C13 C 0.86682(9) 0.65622(13) 0.51617(11) 0.0159(3) Uani 1 1 d . . . . .
C14 C 0.89583(9) 0.62201(14) 0.43381(11) 0.0151(3) Uani 1 1 d . . . . .
C15 C 0.87092(9) 0.51705(14) 0.38956(11) 0.0150(3) Uani 1 1 d . . . . .
C16 C 0.81625(8) 0.44951(14) 0.42606(11) 0.0143(3) Uani 1 1 d . . . . .
H16 H 0.798891 0.379092 0.394904 0.017 Uiso 1 1 calc R U . . .
C17 C 0.87621(10) 0.78983(16) 0.64718(12) 0.0257(4) Uani 1 1 d . . . . .
H17A H 0.901669 0.863142 0.668388 0.039 Uiso 1 1 calc R U . . .
H17B H 0.892829 0.727400 0.692497 0.039 Uiso 1 1 calc R U . . .
H17C H 0.820902 0.799821 0.643484 0.039 Uiso 1 1 calc R U . . .
C18 C 1.02551(9) 0.65754(16) 0.42868(14) 0.0273(4) Uani 1 1 d . . . . .
H18A H 1.032879 0.574869 0.413901 0.041 Uiso 1 1 calc R U . . .
H18B H 1.035444 0.669245 0.497552 0.041 Uiso 1 1 calc R U . . .
H18C H 1.060757 0.705635 0.397331 0.041 Uiso 1 1 calc R U . . .
C19 C 0.88394(12) 0.38044(18) 0.26589(14) 0.0374(5) Uani 1 1 d . . . . .
H19A H 0.829361 0.381810 0.242550 0.056 Uiso 1 1 calc R U . . .
H19B H 0.894665 0.316075 0.311261 0.056 Uiso 1 1 calc R U . . .
H19C H 0.913050 0.369056 0.212346 0.056 Uiso 1 1 calc R U . . .
C20 C 0.52268(8) 0.31008(13) 0.42948(11) 0.0138(3) Uani 1 1 d . . . . .
C21 C 0.52058(9) 0.36213(13) 0.34057(11) 0.0147(3) Uani 1 1 d . . . . .
H21 H 0.562666 0.407596 0.326498 0.018 Uiso 1 1 calc R U . . .
C22 C 0.45743(9) 0.34835(13) 0.27190(11) 0.0152(3) Uani 1 1 d . . . . .
C23 C 0.39564(9) 0.28180(14) 0.29085(11) 0.0154(3) Uani 1 1 d . . . . .
C24 C 0.39656(9) 0.23157(14) 0.38094(11) 0.0163(3) Uani 1 1 d . . . . .
C25 C 0.45942(9) 0.24589(14) 0.44980(11) 0.0149(3) Uani 1 1 d . . . . .
H25 H 0.459339 0.211904 0.510862 0.018 Uiso 1 1 calc R U . . .
C26 C 0.50105(9) 0.49404(14) 0.17040(12) 0.0193(3) Uani 1 1 d . . . . .
H26A H 0.554004 0.466897 0.177109 0.029 Uiso 1 1 calc R U . . .
H26B H 0.495456 0.553695 0.218625 0.029 Uiso 1 1 calc R U . . .
H26C H 0.487390 0.527704 0.107000 0.029 Uiso 1 1 calc R U . . .
C27 C 0.32297(11) 0.15911(16) 0.18070(13) 0.0289(4) Uani 1 1 d . . . . .
H27A H 0.278520 0.159589 0.131787 0.043 Uiso 1 1 calc R U . . .
H27B H 0.315516 0.100675 0.229199 0.043 Uiso 1 1 calc R U . . .
H27C H 0.368674 0.139535 0.151610 0.043 Uiso 1 1 calc R U . . .
C28 C 0.32781(10) 0.12150(17) 0.48503(12) 0.0254(4) Uani 1 1 d . . . . .
H28A H 0.278582 0.082206 0.485009 0.038 Uiso 1 1 calc R U . . .
H28B H 0.332710 0.183939 0.532752 0.038 Uiso 1 1 calc R U . . .
H28C H 0.369060 0.064663 0.500201 0.038 Uiso 1 1 calc R U . . .
O1 O 0.89558(7) 0.75928(10) 0.55527(8) 0.0210(3) Uani 1 1 d . . . . .
O2 O 0.94849(6) 0.69105(10) 0.39535(8) 0.0181(2) Uani 1 1 d . . . . .
O3 O 0.90530(6) 0.48822(10) 0.31152(8) 0.0209(3) Uani 1 1 d . . . . .
O4 O 0.45190(6) 0.39756(10) 0.18275(8) 0.0203(3) Uani 1 1 d . . . . .
O5 O 0.33202(6) 0.27229(10) 0.22379(8) 0.0194(3) Uani 1 1 d . . . . .
O6 O 0.33230(6) 0.17035(11) 0.39383(8) 0.0220(3) Uani 1 1 d . . . . .
C29 C 0.10183(10) 0.45523(15) 0.10341(12) 0.0222(4) Uani 1 1 d . . . . .
H29 H 0.070695 0.388979 0.073173 0.027 Uiso 1 1 calc R U . . .
Cl1 Cl 0.19190(2) 0.40119(4) 0.14941(3) 0.02667(12) Uani 1 1 d . . . . .
Cl2 Cl 0.05516(3) 0.51296(5) 0.19554(4) 0.04094(14) Uani 1 1 d . . . . .
Cl3 Cl 0.10983(3) 0.56297(5) 0.01632(4) 0.04814(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.533(2) . ?
C1 C9 1.538(2) . ?
C1 C6 1.545(2) . ?
C1 C2 1.548(2) . ?
C2 C3 1.540(2) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C20 1.535(2) . ?
C3 C4 1.544(2) . ?
C3 C7 1.547(2) . ?
C4 C5 1.539(2) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C10 1.531(2) . ?
C5 C6 1.534(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.534(2) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C10 1.529(2) . ?
C8 C9 1.532(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.393(2) . ?
C11 C16 1.401(2) . ?
C12 C13 1.393(2) . ?
C12 H12 0.9500 . ?
C13 O1 1.3716(19) . ?
C13 C14 1.392(2) . ?
C14 O2 1.3853(18) . ?
C14 C15 1.399(2) . ?
C15 O3 1.3707(19) . ?
C15 C16 1.389(2) . ?
C16 H16 0.9500 . ?
C17 O1 1.434(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O2 1.436(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O3 1.420(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.391(2) . ?
C20 C25 1.399(2) . ?
C21 C22 1.394(2) . ?
C21 H21 0.9500 . ?
C22 O4 1.3767(19) . ?
C22 C23 1.386(2) . ?
C23 O5 1.3820(18) . ?
C23 C24 1.400(2) . ?
C24 O6 1.3672(19) . ?
C24 C25 1.393(2) . ?
C25 H25 0.9500 . ?
C26 O4 1.4289(19) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 O5 1.431(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 O6 1.421(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 Cl1 1.7552(17) . ?
C29 Cl2 1.7620(18) . ?
C29 Cl3 1.7631(18) . ?
C29 H29 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C9 112.59(12) . . ?
C11 C1 C6 109.84(12) . . ?
C9 C1 C6 108.22(12) . . ?
C11 C1 C2 109.49(12) . . ?
C9 C1 C2 107.93(12) . . ?
C6 C1 C2 108.67(12) . . ?
C3 C2 C1 112.14(12) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2AB 109.2 . . ?
C1 C2 H2AB 109.2 . . ?
H2A C2 H2AB 107.9 . . ?
C20 C3 C2 112.15(12) . . ?
C20 C3 C4 109.34(12) . . ?
C2 C3 C4 107.78(12) . . ?
C20 C3 C7 110.69(12) . . ?
C2 C3 C7 108.16(12) . . ?
C4 C3 C7 108.61(12) . . ?
C5 C4 C3 110.78(13) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4AB 109.5 . . ?
C3 C4 H4AB 109.5 . . ?
H4A C4 H4AB 108.1 . . ?
C10 C5 C6 109.38(13) . . ?
C10 C5 C4 109.81(13) . . ?
C6 C5 C4 109.04(12) . . ?
C10 C5 H5 109.5 . . ?
C6 C5 H5 109.5 . . ?
C4 C5 H5 109.5 . . ?
C5 C6 C1 110.53(12) . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6AB 109.5 . . ?
C1 C6 H6AB 109.5 . . ?
H6A C6 H6AB 108.1 . . ?
C8 C7 C3 110.24(12) . . ?
C8 C7 H7A 109.6 . . ?
C3 C7 H7A 109.6 . . ?
C8 C7 H7AB 109.6 . . ?
C3 C7 H7AB 109.6 . . ?
H7A C7 H7AB 108.1 . . ?
C10 C8 C9 109.82(13) . . ?
C10 C8 C7 109.45(13) . . ?
C9 C8 C7 109.97(13) . . ?
C10 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C7 C8 H8 109.2 . . ?
C8 C9 C1 110.44(13) . . ?
C8 C9 H9A 109.6 . . ?
C1 C9 H9A 109.6 . . ?
C8 C9 H9AB 109.6 . . ?
C1 C9 H9AB 109.6 . . ?
H9A C9 H9AB 108.1 . . ?
C8 C10 C5 109.33(13) . . ?
C8 C10 H10A 109.8 . . ?
C5 C10 H10A 109.8 . . ?
C8 C10 H10B 109.8 . . ?
C5 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C12 C11 C16 119.06(14) . . ?
C12 C11 C1 121.99(14) . . ?
C16 C11 C1 118.96(13) . . ?
C13 C12 C11 120.39(14) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
O1 C13 C14 115.04(14) . . ?
O1 C13 C12 124.44(14) . . ?
C14 C13 C12 120.51(14) . . ?
O2 C14 C13 120.69(14) . . ?
O2 C14 C15 120.04(14) . . ?
C13 C14 C15 119.27(14) . . ?
O3 C15 C16 124.80(14) . . ?
O3 C15 C14 114.96(14) . . ?
C16 C15 C14 120.23(14) . . ?
C15 C16 C11 120.51(14) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 118.84(14) . . ?
C21 C20 C3 121.57(13) . . ?
C25 C20 C3 119.58(13) . . ?
C20 C21 C22 120.76(14) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
O4 C22 C23 115.96(13) . . ?
O4 C22 C21 123.54(14) . . ?
C23 C22 C21 120.50(14) . . ?
O5 C23 C22 120.16(14) . . ?
O5 C23 C24 120.64(14) . . ?
C22 C23 C24 119.04(14) . . ?
O6 C24 C25 124.69(14) . . ?
O6 C24 C23 114.83(13) . . ?
C25 C24 C23 120.49(14) . . ?
C24 C25 C20 120.33(14) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O5 C27 H27A 109.5 . . ?
O5 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O5 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O6 C28 H28A 109.5 . . ?
O6 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O6 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C13 O1 C17 117.23(12) . . ?
C14 O2 C18 112.09(12) . . ?
C15 O3 C19 117.22(13) . . ?
C22 O4 C26 117.09(12) . . ?
C23 O5 C27 113.70(12) . . ?
C24 O6 C28 117.88(13) . . ?
Cl1 C29 Cl2 110.20(9) . . ?
Cl1 C29 Cl3 110.83(9) . . ?
Cl2 C29 Cl3 110.28(10) . . ?
Cl1 C29 H29 108.5 . . ?
Cl2 C29 H29 108.5 . . ?
Cl3 C29 H29 108.5 . . ?

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
C11 C1 C2 C3 178.05(12) . . . . ?
C9 C1 C2 C3 -59.07(16) . . . . ?
C6 C1 C2 C3 58.07(16) . . . . ?
C1 C2 C3 C20 -178.83(12) . . . . ?
C1 C2 C3 C4 -58.42(16) . . . . ?
C1 C2 C3 C7 58.83(16) . . . . ?
C20 C3 C4 C5 -178.44(12) . . . . ?
C2 C3 C4 C5 59.40(15) . . . . ?
C7 C3 C4 C5 -57.56(16) . . . . ?
C3 C4 C5 C10 58.84(16) . . . . ?
C3 C4 C5 C6 -60.99(16) . . . . ?
C10 C5 C6 C1 -60.17(16) . . . . ?
C4 C5 C6 C1 59.92(16) . . . . ?
C11 C1 C6 C5 -177.72(12) . . . . ?
C9 C1 C6 C5 59.00(16) . . . . ?
C2 C1 C6 C5 -57.96(16) . . . . ?
C20 C3 C7 C8 178.60(13) . . . . ?
C2 C3 C7 C8 -58.16(16) . . . . ?
C4 C3 C7 C8 58.56(16) . . . . ?
C3 C7 C8 C10 -60.86(16) . . . . ?
C3 C7 C8 C9 59.87(17) . . . . ?
C10 C8 C9 C1 60.13(16) . . . . ?
C7 C8 C9 C1 -60.38(17) . . . . ?
C11 C1 C9 C8 179.63(12) . . . . ?
C6 C1 C9 C8 -58.77(16) . . . . ?
C2 C1 C9 C8 58.67(16) . . . . ?
C9 C8 C10 C5 -59.94(16) . . . . ?
C7 C8 C10 C5 60.89(16) . . . . ?
C6 C5 C10 C8 59.84(16) . . . . ?
C4 C5 C10 C8 -59.78(16) . . . . ?
C9 C1 C11 C12 -2.0(2) . . . . ?
C6 C1 C11 C12 -122.68(15) . . . . ?
C2 C1 C11 C12 118.06(15) . . . . ?
C9 C1 C11 C16 178.05(13) . . . . ?
C6 C1 C11 C16 57.37(17) . . . . ?
C2 C1 C11 C16 -61.89(17) . . . . ?
C16 C11 C12 C13 0.2(2) . . . . ?
C1 C11 C12 C13 -179.75(14) . . . . ?
C11 C12 C13 O1 -179.96(14) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
O1 C13 C14 O2 -1.4(2) . . . . ?
C12 C13 C14 O2 178.24(13) . . . . ?
O1 C13 C14 C15 178.94(13) . . . . ?
C12 C13 C14 C15 -1.4(2) . . . . ?
O2 C14 C15 O3 3.3(2) . . . . ?
C13 C14 C15 O3 -177.13(14) . . . . ?
O2 C14 C15 C16 -177.83(14) . . . . ?
C13 C14 C15 C16 1.8(2) . . . . ?
O3 C15 C16 C11 177.58(14) . . . . ?
C14 C15 C16 C11 -1.2(2) . . . . ?
C12 C11 C16 C15 0.2(2) . . . . ?
C1 C11 C16 C15 -179.83(14) . . . . ?
C2 C3 C20 C21 4.5(2) . . . . ?
C4 C3 C20 C21 -114.96(15) . . . . ?
C7 C3 C20 C21 125.43(15) . . . . ?
C2 C3 C20 C25 -176.56(13) . . . . ?
C4 C3 C20 C25 63.94(17) . . . . ?
C7 C3 C20 C25 -55.66(18) . . . . ?
C25 C20 C21 C22 -1.6(2) . . . . ?
C3 C20 C21 C22 177.32(14) . . . . ?
C20 C21 C22 O4 179.99(14) . . . . ?
C20 C21 C22 C23 -0.4(2) . . . . ?
O4 C22 C23 O5 -2.9(2) . . . . ?
C21 C22 C23 O5 177.46(14) . . . . ?
O4 C22 C23 C24 -178.40(14) . . . . ?
C21 C22 C23 C24 1.9(2) . . . . ?
O5 C23 C24 O6 2.7(2) . . . . ?
C22 C23 C24 O6 178.21(14) . . . . ?
O5 C23 C24 C25 -177.04(14) . . . . ?
C22 C23 C24 C25 -1.5(2) . . . . ?
O6 C24 C25 C20 179.85(14) . . . . ?
C23 C24 C25 C20 -0.4(2) . . . . ?
C21 C20 C25 C24 2.0(2) . . . . ?
C3 C20 C25 C24 -176.95(14) . . . . ?
C14 C13 O1 C17 -171.11(14) . . . . ?
C12 C13 O1 C17 9.2(2) . . . . ?
C13 C14 O2 C18 93.10(17) . . . . ?
C15 C14 O2 C18 -87.29(17) . . . . ?
C16 C15 O3 C19 -1.0(2) . . . . ?
C14 C15 O3 C19 177.90(16) . . . . ?
C23 C22 O4 C26 160.68(14) . . . . ?
C21 C22 O4 C26 -19.7(2) . . . . ?
C22 C23 O5 C27 109.07(17) . . . . ?
C24 C23 O5 C27 -75.48(19) . . . . ?
C25 C24 O6 C28 2.6(2) . . . . ?
C23 C24 O6 C28 -177.17(14) . . . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1575310'
_audit_update_record             
;
2017-09-19 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H43 F6 N O6 P'
_chemical_formula_weight         706.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.6564(11)
_cell_length_b                   13.3543(15)
_cell_length_c                   14.3477(16)
_cell_angle_alpha                67.011(4)
_cell_angle_beta                 76.108(4)
_cell_angle_gamma                80.955(4)
_cell_volume                     1649.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      78.39

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             742
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.449
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8093
_exptl_absorpt_correction_T_max  0.9410
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            19948
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.604
_diffrn_reflns_theta_max         78.962
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             6510
_reflns_number_gt                5780
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0620P)²+6.7474P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0047(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6510
_refine_ls_number_parameters     441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.2094
_refine_ls_wR_factor_gt          0.2033
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_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
C1 C 0.5518(4) 0.0917(3) 0.6195(2) 0.0164(7) Uani 1 1 d . . . . .
C2 C 0.4928(4) 0.1552(3) 0.6926(2) 0.0143(6) Uani 1 1 d . . . . .
H2A H 0.564847 0.204501 0.684862 0.017 Uiso 1 1 calc R U . . .
H2B H 0.405641 0.200624 0.672398 0.017 Uiso 1 1 calc R U . . .
C3 C 0.4564(4) 0.0781(3) 0.8069(2) 0.0152(7) Uani 1 1 d . . . . .
C4 C 0.5933(4) 0.0078(3) 0.8368(3) 0.0179(7) Uani 1 1 d . . . . .
H4A H 0.666572 0.055374 0.830764 0.021 Uiso 1 1 calc R U . . .
H4B H 0.571704 -0.043314 0.909370 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6516(4) -0.0567(3) 0.7657(3) 0.0206(7) Uani 1 1 d . . . . .
H5 H 0.740608 -0.101296 0.785696 0.025 Uiso 1 1 calc R U . . .
C6 C 0.6867(4) 0.0218(3) 0.6529(3) 0.0207(7) Uani 1 1 d . . . . .
H6A H 0.725955 -0.020441 0.607813 0.025 Uiso 1 1 calc R U . . .
H6B H 0.760346 0.069867 0.645195 0.025 Uiso 1 1 calc R U . . .
C7 C 0.4390(4) 0.0144(3) 0.6333(3) 0.0207(7) Uani 1 1 d . . . . .
H7A H 0.350697 0.057717 0.612881 0.025 Uiso 1 1 calc R U . . .
H7B H 0.475735 -0.027853 0.587932 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3450(4) 0.0019(3) 0.8161(3) 0.0182(7) Uani 1 1 d . . . . .
H8A H 0.320045 -0.048644 0.888709 0.022 Uiso 1 1 calc R U . . .
H8B H 0.256879 0.045774 0.795980 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5404(4) -0.1326(3) 0.7768(3) 0.0237(8) Uani 1 1 d . . . . .
H9A H 0.578480 -0.175060 0.731837 0.028 Uiso 1 1 calc R U . . .
H9B H 0.518446 -0.184346 0.849162 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4048(4) -0.0640(3) 0.7460(3) 0.0217(8) Uani 1 1 d . . . . .
H10 H 0.331495 -0.113259 0.753583 0.026 Uiso 1 1 calc R U . . .
C11 C 0.5809(4) 0.1741(3) 0.5084(3) 0.0177(7) Uani 1 1 d . . . . .
C12 C 0.7161(4) 0.1825(3) 0.4449(3) 0.0209(7) Uani 1 1 d . . . . .
H12 H 0.794067 0.134669 0.469856 0.025 Uiso 1 1 calc R U . . .
C13 C 0.7380(4) 0.2609(3) 0.3444(3) 0.0222(8) Uani 1 1 d . . . . .
C14 C 0.6265(4) 0.3324(3) 0.3064(3) 0.0200(7) Uani 1 1 d . . . . .
C15 C 0.4907(4) 0.3242(3) 0.3703(3) 0.0200(7) Uani 1 1 d . . . . .
C16 C 0.4679(4) 0.2453(3) 0.4697(3) 0.0183(7) Uani 1 1 d . . . . .
H16 H 0.374718 0.239813 0.511593 0.022 Uiso 1 1 calc R U . . .
C17 C 0.9848(5) 0.1985(4) 0.3082(4) 0.0400(11) Uani 1 1 d . . . . .
H17A H 0.960509 0.124799 0.322005 0.060 Uiso 1 1 calc R U . . .
H17B H 1.004493 0.201430 0.370923 0.060 Uiso 1 1 calc R U . . .
H17C H 1.069755 0.216882 0.252939 0.060 Uiso 1 1 calc R U . . .
C18 C 0.5991(5) 0.3916(3) 0.1335(3) 0.0286(9) Uani 1 1 d . . . . .
H18A H 0.603039 0.456851 0.070207 0.043 Uiso 1 1 calc R U . . .
H18B H 0.500279 0.370780 0.160428 0.043 Uiso 1 1 calc R U . . .
H18C H 0.659867 0.331731 0.118085 0.043 Uiso 1 1 calc R U . . .
C19 C 0.2437(5) 0.3826(4) 0.3840(4) 0.0401(11) Uani 1 1 d . . . . .
H19A H 0.178742 0.439929 0.346377 0.060 Uiso 1 1 calc R U . . .
H19B H 0.235783 0.384997 0.452448 0.060 Uiso 1 1 calc R U . . .
H19C H 0.218208 0.311244 0.391475 0.060 Uiso 1 1 calc R U . . .
C20 C 0.4005(4) 0.1466(3) 0.8742(2) 0.0150(7) Uani 1 1 d . . . . .
C21 C 0.2590(4) 0.1453(3) 0.9294(3) 0.0174(7) Uani 1 1 d . . . . .
H21 H 0.194184 0.101663 0.924589 0.021 Uiso 1 1 calc R U . . .
C22 C 0.2129(4) 0.2076(3) 0.9913(3) 0.0189(7) Uani 1 1 d . . . . .
C23 C 0.3046(4) 0.2746(3) 0.9973(3) 0.0180(7) Uani 1 1 d . . . . .
C24 C 0.4458(4) 0.2768(3) 0.9417(2) 0.0167(7) Uani 1 1 d . . . . .
C25 C 0.4928(4) 0.2134(3) 0.8814(2) 0.0150(6) Uani 1 1 d . . . . .
H25 H 0.588881 0.215316 0.844619 0.018 Uiso 1 1 calc R U . . .
C26 C -0.0139(5) 0.1291(4) 1.0599(4) 0.0350(10) Uani 1 1 d . . . . .
H26A H -0.105366 0.137461 1.104866 0.052 Uiso 1 1 calc R U . . .
H26B H 0.030651 0.055620 1.090024 0.052 Uiso 1 1 calc R U . . .
H26C H -0.030372 0.140259 0.991641 0.052 Uiso 1 1 calc R U . . .
C27 C 0.1519(5) 0.4158(3) 1.0373(3) 0.0305(9) Uani 1 1 d . . . . .
H27A H 0.141619 0.460623 1.079050 0.046 Uiso 1 1 calc R U . . .
H27B H 0.062176 0.382006 1.051813 0.046 Uiso 1 1 calc R U . . .
H27C H 0.174571 0.461793 0.963876 0.046 Uiso 1 1 calc R U . . .
C28 C 0.6690(4) 0.3565(4) 0.8896(3) 0.0320(9) Uani 1 1 d . . . . .
H28A H 0.724519 0.285855 0.906957 0.048 Uiso 1 1 calc R U . . .
H28B H 0.716757 0.408360 0.902054 0.048 Uiso 1 1 calc R U . . .
H28C H 0.661947 0.384028 0.816712 0.048 Uiso 1 1 calc R U . . .
O1 O 0.8674(3) 0.2750(2) 0.2770(2) 0.0323(7) Uani 1 1 d . . . . .
O2 O 0.6495(3) 0.4144(2) 0.20949(18) 0.0237(6) Uani 1 1 d . . . . .
O3 O 0.3870(3) 0.3993(2) 0.3281(2) 0.0267(6) Uani 1 1 d . . . . .
O4 O 0.0785(3) 0.2078(2) 1.0500(2) 0.0271(6) Uani 1 1 d . . . . .
O5 O 0.2649(3) 0.3325(2) 1.0622(2) 0.0244(6) Uani 1 1 d . . . . .
O6 O 0.5290(3) 0.3437(2) 0.95251(19) 0.0213(5) Uani 1 1 d . . . . .
C29 C 0.5655(4) 0.5048(3) 0.4600(3) 0.0207(7) Uani 1 1 d . . . . .
C30 C 0.6942(4) 0.4475(3) 0.4831(3) 0.0300(9) Uani 1 1 d . . . . .
H30 H 0.699003 0.400926 0.552174 0.036 Uiso 1 1 calc R U . . .
C31 C 0.8147(5) 0.4582(4) 0.4063(3) 0.0308(9) Uani 1 1 d . . . . .
H31 H 0.901938 0.418562 0.422683 0.037 Uiso 1 1 calc R U . . .
C32 C 0.6878(4) 0.5803(3) 0.2834(3) 0.0228(8) Uani 1 1 d . . . . .
H32 H 0.686154 0.626544 0.213814 0.027 Uiso 1 1 calc R U . . .
C33 C 0.5661(4) 0.5718(3) 0.3568(3) 0.0219(7) Uani 1 1 d . . . . .
H33 H 0.480416 0.611946 0.337591 0.026 Uiso 1 1 calc R U . . .
C34 C 0.9367(5) 0.5296(4) 0.2256(3) 0.0315(9) Uani 1 1 d . . . . .
H34A H 0.931443 0.599423 0.167816 0.047 Uiso 1 1 calc R U . . .
H34B H 0.939694 0.469699 0.201719 0.047 Uiso 1 1 calc R U . . .
H34C H 1.023209 0.523294 0.252402 0.047 Uiso 1 1 calc R U . . .
N1 N 0.8093(4) 0.5242(3) 0.3084(2) 0.0240(7) Uani 1 1 d . . . . .
P1 P -0.02404(10) 0.25073(8) 0.66911(7) 0.0257(3) Uani 1 1 d . . . . .
F1 F -0.0280(3) 0.2525(3) 0.7803(2) 0.0454(7) Uani 1 1 d . . . . .
F2 F -0.0154(4) 0.1220(2) 0.7153(2) 0.0564(8) Uani 1 1 d . . . . .
F3 F -0.0218(3) 0.2513(2) 0.5571(2) 0.0434(7) Uani 1 1 d . . . . .
F4 F -0.0344(3) 0.3818(2) 0.6213(2) 0.0476(7) Uani 1 1 d . . . . .
F5 F -0.1948(3) 0.2550(3) 0.6928(2) 0.0451(7) Uani 1 1 d . . . . .
F6 F 0.1450(3) 0.2508(3) 0.6450(2) 0.0543(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.530(4) . ?
C1 C6 1.539(5) . ?
C1 C7 1.542(5) . ?
C1 C2 1.549(4) . ?
C2 C3 1.546(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C20 1.532(4) . ?
C3 C4 1.543(5) . ?
C3 C8 1.543(4) . ?
C4 C5 1.535(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C9 1.529(5) . ?
C5 C6 1.535(5) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C10 1.534(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.540(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.528(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 1.0000 . ?
C11 C12 1.394(5) . ?
C11 C16 1.398(5) . ?
C12 C13 1.402(5) . ?
C12 H12 0.9500 . ?
C13 O1 1.372(4) . ?
C13 C14 1.385(5) . ?
C14 O2 1.386(4) . ?
C14 C15 1.401(5) . ?
C15 O3 1.370(4) . ?
C15 C16 1.393(5) . ?
C16 H16 0.9500 . ?
C17 O1 1.433(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O2 1.442(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O3 1.425(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.402(5) . ?
C20 C21 1.404(5) . ?
C21 C22 1.396(5) . ?
C21 H21 0.9500 . ?
C22 O4 1.368(4) . ?
C22 C23 1.392(5) . ?
C23 O5 1.382(4) . ?
C23 C24 1.403(5) . ?
C24 O6 1.364(4) . ?
C24 C25 1.390(5) . ?
C25 H25 0.9500 . ?
C26 O4 1.427(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 O5 1.433(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 O6 1.428(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.392(5) . ?
C29 C33 1.399(5) . ?
C29 C29 1.474(7) 2_666 ?
C30 C31 1.379(6) . ?
C30 H30 0.9500 . ?
C31 N1 1.345(5) . ?
C31 H31 0.9500 . ?
C32 N1 1.334(5) . ?
C32 C33 1.363(5) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 N1 1.479(5) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
P1 F2 1.579(3) . ?
P1 F6 1.586(3) . ?
P1 F1 1.596(3) . ?
P1 F5 1.598(3) . ?
P1 F3 1.599(3) . ?
P1 F4 1.608(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C6 113.0(3) . . ?
C11 C1 C7 110.7(3) . . ?
C6 C1 C7 108.2(3) . . ?
C11 C1 C2 108.4(3) . . ?
C6 C1 C2 107.9(3) . . ?
C7 C1 C2 108.5(3) . . ?
C3 C2 C1 112.1(3) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C20 C3 C4 110.8(3) . . ?
C20 C3 C8 112.2(3) . . ?
C4 C3 C8 108.4(3) . . ?
C20 C3 C2 109.0(3) . . ?
C4 C3 C2 108.4(3) . . ?
C8 C3 C2 107.9(3) . . ?
C5 C4 C3 110.2(3) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C9 C5 C6 109.4(3) . . ?
C9 C5 C4 109.8(3) . . ?
C6 C5 C4 110.1(3) . . ?
C9 C5 H5 109.2 . . ?
C6 C5 H5 109.2 . . ?
C4 C5 H5 109.2 . . ?
C5 C6 C1 110.5(3) . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C10 C7 C1 110.3(3) . . ?
C10 C7 H7A 109.6 . . ?
C1 C7 H7A 109.6 . . ?
C10 C7 H7B 109.6 . . ?
C1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C10 C8 C3 110.4(3) . . ?
C10 C8 H8A 109.6 . . ?
C3 C8 H8A 109.6 . . ?
C10 C8 H8B 109.6 . . ?
C3 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C5 108.9(3) . . ?
C10 C9 H9A 109.9 . . ?
C5 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C5 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C9 C10 C7 109.6(3) . . ?
C9 C10 C8 110.1(3) . . ?
C7 C10 C8 109.5(3) . . ?
C9 C10 H10 109.2 . . ?
C7 C10 H10 109.2 . . ?
C8 C10 H10 109.2 . . ?
C12 C11 C16 118.6(3) . . ?
C12 C11 C1 122.7(3) . . ?
C16 C11 C1 118.7(3) . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
O1 C13 C14 114.8(3) . . ?
O1 C13 C12 124.3(3) . . ?
C14 C13 C12 120.9(3) . . ?
C13 C14 O2 121.1(3) . . ?
C13 C14 C15 118.6(3) . . ?
O2 C14 C15 120.2(3) . . ?
O3 C15 C16 124.2(3) . . ?
O3 C15 C14 115.1(3) . . ?
C16 C15 C14 120.7(3) . . ?
C15 C16 C11 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 118.4(3) . . ?
C25 C20 C3 119.4(3) . . ?
C21 C20 C3 122.2(3) . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
O4 C22 C23 115.1(3) . . ?
O4 C22 C21 123.9(3) . . ?
C23 C22 C21 120.9(3) . . ?
O5 C23 C22 122.3(3) . . ?
O5 C23 C24 118.7(3) . . ?
C22 C23 C24 118.8(3) . . ?
O6 C24 C25 124.4(3) . . ?
O6 C24 C23 115.2(3) . . ?
C25 C24 C23 120.4(3) . . ?
C24 C25 C20 121.0(3) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O5 C27 H27A 109.5 . . ?
O5 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O5 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O6 C28 H28A 109.5 . . ?
O6 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O6 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C13 O1 C17 117.7(3) . . ?
C14 O2 C18 113.1(3) . . ?
C15 O3 C19 116.4(3) . . ?
C22 O4 C26 118.1(3) . . ?
C23 O5 C27 114.8(3) . . ?
C24 O6 C28 117.0(3) . . ?
C30 C29 C33 116.8(3) . . ?
C30 C29 C29 121.9(4) . 2_666 ?
C33 C29 C29 121.3(4) . 2_666 ?
C31 C30 C29 120.4(4) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
N1 C31 C30 120.3(4) . . ?
N1 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
N1 C32 C33 120.7(3) . . ?
N1 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C32 C33 C29 120.9(4) . . ?
C32 C33 H33 119.5 . . ?
C29 C33 H33 119.5 . . ?
N1 C34 H34A 109.5 . . ?
N1 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N1 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 N1 C31 120.9(3) . . ?
C32 N1 C34 119.1(3) . . ?
C31 N1 C34 119.8(3) . . ?
F2 P1 F6 91.16(19) . . ?
F2 P1 F1 90.36(17) . . ?
F6 P1 F1 89.61(16) . . ?
F2 P1 F5 90.74(18) . . ?
F6 P1 F5 178.05(19) . . ?
F1 P1 F5 89.93(15) . . ?
F2 P1 F3 90.68(17) . . ?
F6 P1 F3 90.90(16) . . ?
F1 P1 F3 178.83(17) . . ?
F5 P1 F3 89.53(15) . . ?
F2 P1 F4 179.22(17) . . ?
F6 P1 F4 89.40(18) . . ?
F1 P1 F4 90.19(16) . . ?
F5 P1 F4 88.72(16) . . ?
F3 P1 F4 88.77(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 178.6(3) . . . . ?
C6 C1 C2 C3 -58.8(3) . . . . ?
C7 C1 C2 C3 58.3(3) . . . . ?
C1 C2 C3 C20 179.4(3) . . . . ?
C1 C2 C3 C4 58.7(3) . . . . ?
C1 C2 C3 C8 -58.5(4) . . . . ?
C20 C3 C4 C5 -177.6(3) . . . . ?
C8 C3 C4 C5 58.8(3) . . . . ?
C2 C3 C4 C5 -58.0(3) . . . . ?
C3 C4 C5 C9 -60.8(4) . . . . ?
C3 C4 C5 C6 59.7(4) . . . . ?
C9 C5 C6 C1 60.5(4) . . . . ?
C4 C5 C6 C1 -60.3(4) . . . . ?
C11 C1 C6 C5 178.3(3) . . . . ?
C7 C1 C6 C5 -58.7(3) . . . . ?
C2 C1 C6 C5 58.5(3) . . . . ?
C11 C1 C7 C10 -177.0(3) . . . . ?
C6 C1 C7 C10 58.6(4) . . . . ?
C2 C1 C7 C10 -58.2(4) . . . . ?
C20 C3 C8 C10 179.1(3) . . . . ?
C4 C3 C8 C10 -58.2(3) . . . . ?
C2 C3 C8 C10 59.0(4) . . . . ?
C6 C5 C9 C10 -60.5(4) . . . . ?
C4 C5 C9 C10 60.4(4) . . . . ?
C5 C9 C10 C7 60.7(3) . . . . ?
C5 C9 C10 C8 -59.8(4) . . . . ?
C1 C7 C10 C9 -60.5(4) . . . . ?
C1 C7 C10 C8 60.3(4) . . . . ?
C3 C8 C10 C9 59.6(4) . . . . ?
C3 C8 C10 C7 -61.0(4) . . . . ?
C6 C1 C11 C12 1.0(4) . . . . ?
C7 C1 C11 C12 -120.6(4) . . . . ?
C2 C1 C11 C12 120.5(3) . . . . ?
C6 C1 C11 C16 -177.8(3) . . . . ?
C7 C1 C11 C16 60.6(4) . . . . ?
C2 C1 C11 C16 -58.3(4) . . . . ?
C16 C11 C12 C13 0.1(5) . . . . ?
C1 C11 C12 C13 -178.6(3) . . . . ?
C11 C12 C13 O1 179.8(3) . . . . ?
C11 C12 C13 C14 0.7(5) . . . . ?
O1 C13 C14 O2 -3.2(5) . . . . ?
C12 C13 C14 O2 176.0(3) . . . . ?
O1 C13 C14 C15 -179.7(3) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C13 C14 C15 O3 178.5(3) . . . . ?
O2 C14 C15 O3 2.0(5) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
O2 C14 C15 C16 -177.0(3) . . . . ?
O3 C15 C16 C11 -177.6(3) . . . . ?
C14 C15 C16 C11 1.2(5) . . . . ?
C12 C11 C16 C15 -1.1(5) . . . . ?
C1 C11 C16 C15 177.7(3) . . . . ?
C4 C3 C20 C25 53.3(4) . . . . ?
C8 C3 C20 C25 174.7(3) . . . . ?
C2 C3 C20 C25 -65.9(4) . . . . ?
C4 C3 C20 C21 -126.7(3) . . . . ?
C8 C3 C20 C21 -5.4(4) . . . . ?
C2 C3 C20 C21 114.0(3) . . . . ?
C25 C20 C21 C22 -1.2(5) . . . . ?
C3 C20 C21 C22 178.9(3) . . . . ?
C20 C21 C22 O4 -177.7(3) . . . . ?
C20 C21 C22 C23 1.9(5) . . . . ?
O4 C22 C23 O5 3.3(5) . . . . ?
C21 C22 C23 O5 -176.2(3) . . . . ?
O4 C22 C23 C24 178.3(3) . . . . ?
C21 C22 C23 C24 -1.3(5) . . . . ?
O5 C23 C24 O6 -4.3(5) . . . . ?
C22 C23 C24 O6 -179.4(3) . . . . ?
O5 C23 C24 C25 175.3(3) . . . . ?
C22 C23 C24 C25 0.2(5) . . . . ?
O6 C24 C25 C20 -180.0(3) . . . . ?
C23 C24 C25 C20 0.5(5) . . . . ?
C21 C20 C25 C24 0.0(5) . . . . ?
C3 C20 C25 C24 179.9(3) . . . . ?
C14 C13 O1 C17 -175.2(4) . . . . ?
C12 C13 O1 C17 5.6(6) . . . . ?
C13 C14 O2 C18 104.9(4) . . . . ?
C15 C14 O2 C18 -78.6(4) . . . . ?
C16 C15 O3 C19 -10.8(5) . . . . ?
C14 C15 O3 C19 170.3(4) . . . . ?
C23 C22 O4 C26 -170.6(3) . . . . ?
C21 C22 O4 C26 8.9(5) . . . . ?
C22 C23 O5 C27 -65.5(4) . . . . ?
C24 C23 O5 C27 119.6(4) . . . . ?
C25 C24 O6 C28 6.3(5) . . . . ?
C23 C24 O6 C28 -174.1(3) . . . . ?
C33 C29 C30 C31 0.1(6) . . . . ?
C29 C29 C30 C31 179.8(4) 2_666 . . . ?
C29 C30 C31 N1 0.3(6) . . . . ?
N1 C32 C33 C29 0.4(5) . . . . ?
C30 C29 C33 C32 -0.4(5) . . . . ?
C29 C29 C33 C32 179.9(4) 2_666 . . . ?
C33 C32 N1 C31 0.0(6) . . . . ?
C33 C32 N1 C34 175.8(3) . . . . ?
C30 C31 N1 C32 -0.3(6) . . . . ?
C30 C31 N1 C34 -176.1(4) . . . . ?

_refine_diff_density_max         0.734
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1575311'
_audit_update_record             
;
2017-09-19 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37.84 H49 O9.66'
_chemical_formula_weight         658.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.1729(16)
_cell_length_b                   13.993(2)
_cell_length_c                   14.345(2)
_cell_angle_alpha                63.733(4)
_cell_angle_beta                 84.981(4)
_cell_angle_gamma                74.713(4)
_cell_volume                     1765.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9147
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      78.30

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             707
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.722
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8623
_exptl_absorpt_correction_T_max  0.9283
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            21711
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.640
_diffrn_reflns_theta_max         78.599
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             7014
_reflns_number_gt                6572
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0621P)²+0.8078P] 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         7014
_refine_ls_number_parameters     472
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
C1 C 0.27365(13) 0.25838(10) 0.37501(10) 0.0193(3) Uani 1 1 d . . . . .
C2 C 0.23372(13) 0.35772(10) 0.26785(10) 0.0194(3) Uani 1 1 d . . . . .
H2A H 0.315178 0.385082 0.237390 0.023 Uiso 1 1 calc R U . . .
H2B H 0.200898 0.333819 0.220665 0.023 Uiso 1 1 calc R U . . .
C3 C 0.12147(13) 0.45180(10) 0.27629(10) 0.0191(3) Uani 1 1 d . . . . .
C4 C 0.17285(13) 0.48637(10) 0.35199(10) 0.0191(3) Uani 1 1 d . . . . .
H4A H 0.254315 0.514588 0.323536 0.023 Uiso 1 1 calc R U . . .
H4B H 0.101258 0.546755 0.357943 0.023 Uiso 1 1 calc R U . . .
C5 C 0.20947(13) 0.38973(10) 0.46080(10) 0.0187(3) Uani 1 1 d . . . . .
C6 C 0.32160(13) 0.29776(10) 0.44805(10) 0.0189(2) Uani 1 1 d . . . . .
H6A H 0.403357 0.325555 0.419630 0.023 Uiso 1 1 calc R U . . .
H6B H 0.347614 0.234606 0.517120 0.023 Uiso 1 1 calc R U . . .
C7 C 0.14561(14) 0.21667(10) 0.42082(10) 0.0213(3) Uani 1 1 d . . . . .
H7A H 0.112635 0.190794 0.375363 0.026 Uiso 1 1 calc R U . . .
H7B H 0.168792 0.153842 0.490410 0.026 Uiso 1 1 calc R U . . .
C8 C -0.00416(13) 0.40767(11) 0.32259(10) 0.0206(3) Uani 1 1 d . . . . .
H8A H -0.077391 0.466732 0.329264 0.025 Uiso 1 1 calc R U . . .
H8B H -0.038543 0.384351 0.275567 0.025 Uiso 1 1 calc R U . . .
C9 C 0.08224(13) 0.34620(11) 0.50398(10) 0.0205(3) Uani 1 1 d . . . . .
H9A H 0.104535 0.283173 0.573541 0.025 Uiso 1 1 calc R U . . .
H9B H 0.008958 0.404798 0.511371 0.025 Uiso 1 1 calc R U . . .
C10 C 0.03311(13) 0.30956(11) 0.42982(10) 0.0206(3) Uani 1 1 d . . . . .
H10 H -0.049562 0.281603 0.458467 0.025 Uiso 1 1 calc R U . . .
C11 C 0.38587(14) 0.16986(10) 0.35954(10) 0.0215(3) Uani 1 1 d . . . . .
C12 C 0.35608(15) 0.11732(11) 0.30320(11) 0.0259(3) Uani 1 1 d . . . . .
H12 H 0.265648 0.134535 0.277668 0.031 Uiso 1 1 calc R U . . .
C13 C 0.45861(16) 0.04009(11) 0.28462(11) 0.0272(3) Uani 1 1 d . . . . .
C14 C 0.59211(15) 0.01511(10) 0.32032(11) 0.0259(3) Uani 1 1 d . . . . .
C15 C 0.62232(14) 0.06906(10) 0.37430(10) 0.0238(3) Uani 1 1 d . . . . .
C16 C 0.51931(14) 0.14462(10) 0.39498(10) 0.0221(3) Uani 1 1 d . . . . .
H16 H 0.540450 0.179235 0.433667 0.027 Uiso 1 1 calc R U . . .
C17 C 0.30445(19) 0.00583(15) 0.19320(14) 0.0416(4) Uani 1 1 d . . . . .
H17A H 0.274763 0.083554 0.143513 0.062 Uiso 1 1 calc R U . . .
H17B H 0.242205 -0.010154 0.251168 0.062 Uiso 1 1 calc R U . . .
H17C H 0.303858 -0.040546 0.158358 0.062 Uiso 1 1 calc R U . . .
C18 C 0.7657(3) -0.02248(17) 0.2147(2) 0.0721(8) Uani 1 1 d . . . . .
H18A H 0.836463 -0.082789 0.209637 0.108 Uiso 1 1 calc R U . . .
H18B H 0.808253 0.031220 0.217887 0.108 Uiso 1 1 calc R U . . .
H18C H 0.703631 0.013551 0.153461 0.108 Uiso 1 1 calc R U . . .
C19 C 0.79005(15) 0.08688(13) 0.46811(13) 0.0328(3) Uani 1 1 d . . . . .
H19A H 0.887993 0.059471 0.485702 0.049 Uiso 1 1 calc R U . . .
H19B H 0.738749 0.063541 0.532014 0.049 Uiso 1 1 calc R U . . .
H19C H 0.766393 0.167483 0.431540 0.049 Uiso 1 1 calc R U . . .
C20 C 0.09216(13) 0.54909(10) 0.16839(10) 0.0207(3) Uani 1 1 d . . . . .
C21 C -0.02879(14) 0.57905(11) 0.11210(10) 0.0227(3) Uani 1 1 d . . . . .
H21 H -0.096355 0.539310 0.141433 0.027 Uiso 1 1 calc R U . . .
C22 C -0.05138(14) 0.66710(11) 0.01287(11) 0.0241(3) Uani 1 1 d . . . . .
C23 C 0.04553(15) 0.72751(11) -0.02966(11) 0.0252(3) Uani 1 1 d . . . . .
C24 C 0.16774(14) 0.69649(11) 0.02565(11) 0.0259(3) Uani 1 1 d . . . . .
C25 C 0.19131(14) 0.60770(11) 0.12366(11) 0.0250(3) Uani 1 1 d . . . . .
H25 H 0.275181 0.586709 0.160472 0.030 Uiso 1 1 calc R U . . .
C26 C -0.26040(15) 0.63394(14) -0.01358(11) 0.0304(3) Uani 1 1 d . . . . .
H26A H -0.335140 0.664765 -0.065491 0.046 Uiso 1 1 calc R U . . .
H26B H -0.297175 0.631369 0.052721 0.046 Uiso 1 1 calc R U . . .
H26C H -0.213535 0.559290 -0.004152 0.046 Uiso 1 1 calc R U . . .
C27 C 0.0739(2) 0.79811(15) -0.20948(12) 0.0419(4) Uani 1 1 d . . . . .
H27A H 0.038722 0.740228 -0.211523 0.063 Uiso 1 1 calc R U . . .
H27B H 0.173510 0.773858 -0.201193 0.063 Uiso 1 1 calc R U . . .
H27C H 0.047770 0.865372 -0.274473 0.063 Uiso 1 1 calc R U . . .
C28 C 0.3798(2) 0.73503(18) 0.03321(17) 0.0586(6) Uani 1 1 d . . . . .
H28A H 0.434523 0.786494 -0.008779 0.088 Uiso 1 1 calc R U . . .
H28B H 0.432029 0.659532 0.049468 0.088 Uiso 1 1 calc R U . . .
H28C H 0.356811 0.742211 0.097988 0.088 Uiso 1 1 calc R U . . .
C29 C 0.26499(13) 0.42367(11) 0.53463(10) 0.0201(3) Uani 1 1 d . . . . .
C30 C 0.29123(13) 0.52675(11) 0.49902(10) 0.0215(3) Uani 1 1 d . . . . .
H30 H 0.268413 0.579149 0.428856 0.026 Uiso 1 1 calc R U . . .
C31 C 0.35063(13) 0.55426(11) 0.56497(11) 0.0225(3) Uani 1 1 d . . . . .
C32 C 0.38371(14) 0.47901(12) 0.66839(11) 0.0240(3) Uani 1 1 d . . . . .
C33 C 0.35310(14) 0.37680(11) 0.70537(10) 0.0235(3) Uani 1 1 d . . . . .
C34 C 0.29532(14) 0.34886(11) 0.63910(10) 0.0225(3) Uani 1 1 d . . . . .
H34 H 0.276493 0.278693 0.665071 0.027 Uiso 1 1 calc R U . . .
C35 C 0.36111(16) 0.72740(12) 0.42559(12) 0.0294(3) Uani 1 1 d . . . . .
H35A H 0.408746 0.688717 0.384897 0.044 Uiso 1 1 calc R U . . .
H35B H 0.398086 0.790392 0.411068 0.044 Uiso 1 1 calc R U . . .
H35C H 0.263591 0.753475 0.406534 0.044 Uiso 1 1 calc R U . . .
C36 C 0.37395(16) 0.57955(12) 0.76620(11) 0.0291(3) Uani 1 1 d . . . . .
H36A H 0.346401 0.651091 0.705621 0.044 Uiso 1 1 calc R U . . .
H36B H 0.428434 0.585900 0.815277 0.044 Uiso 1 1 calc R U . . .
H36C H 0.292571 0.556305 0.800255 0.044 Uiso 1 1 calc R U . . .
C37 C 0.34620(19) 0.20721(13) 0.85153(12) 0.0364(4) Uani 1 1 d . . . . .
H37A H 0.246976 0.223254 0.843562 0.055 Uiso 1 1 calc R U . . .
H37B H 0.373153 0.166358 0.925547 0.055 Uiso 1 1 calc R U . . .
H37C H 0.390363 0.162819 0.815067 0.055 Uiso 1 1 calc R U . . .
O1 O 0.43877(12) -0.01650(9) 0.23174(9) 0.0372(3) Uani 1 1 d . . . . .
O2 O 0.69173(11) -0.06480(8) 0.30531(8) 0.0320(2) Uani 1 1 d . . . . .
O3 O 0.75659(10) 0.04346(8) 0.40278(8) 0.0298(2) Uani 1 1 d . . . . .
O4 O -0.16635(11) 0.70147(9) -0.04826(8) 0.0309(2) Uani 1 1 d . . . . .
O5 O 0.01827(11) 0.81968(8) -0.12426(8) 0.0304(2) Uani 1 1 d . . . . .
O6 O 0.25761(11) 0.75952(9) -0.02355(8) 0.0345(3) Uani 1 1 d . . . . .
O7 O 0.37995(10) 0.65394(8) 0.53387(8) 0.0274(2) Uani 1 1 d . . . . .
O8 O 0.45303(10) 0.50018(9) 0.73341(8) 0.0307(2) Uani 1 1 d . . . . .
O9 O 0.38725(11) 0.30818(8) 0.80834(8) 0.0306(2) Uani 1 1 d . . . . .
C1A C 0.054(2) -0.0034(14) 0.0212(16) 0.083(6) Uani 0.420(4) 1 d . . P A -1
H1AA H 0.114212 0.047216 -0.011259 0.100 Uiso 0.420(4) 1 calc R U P A -1
H1AB H 0.100246 -0.072083 0.015171 0.100 Uiso 0.420(4) 1 calc R U P A -1
C2A C -0.0646(17) 0.0438(13) -0.0452(14) 0.063(3) Uani 0.420(4) 1 d . . P A -1
H2AA H -0.144798 0.059480 -0.006218 0.094 Uiso 0.420(4) 1 calc R U P A -1
H2AB H -0.075527 -0.007891 -0.071046 0.094 Uiso 0.420(4) 1 calc R U P A -1
H2AC H -0.055260 0.112424 -0.104090 0.094 Uiso 0.420(4) 1 calc R U P A -1
O1A O 0.0579(4) -0.0318(3) 0.1318(4) 0.0709(13) Uani 0.420(4) 1 d . . P A -1
H1AO H 0.036321 0.026064 0.140146 0.106 Uiso 0.420(4) 1 calc R U P A -1
O1B O 0.0229(5) 0.9134(4) 0.3541(4) 0.0377(19) Uani 0.243(6) 1 d . . P . .
H1BA H -0.071(13) 0.926(9) 0.355(8) 0.06(3) Uiso 0.243(6) 1 d . . P . .
H1BB H 0.034(8) 0.909(7) 0.293(7) 0.04(2) Uiso 0.243(6) 1 d . . P . .


_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
C1 C11 1.5297(17) . ?
C1 C2 1.5429(17) . ?
C1 C7 1.5429(18) . ?
C1 C6 1.5433(16) . ?
C2 C3 1.5414(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C20 1.5296(18) . ?
C3 C8 1.5364(17) . ?
C3 C4 1.5440(16) . ?
C4 C5 1.5400(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C29 1.5354(16) . ?
C5 C9 1.5399(17) . ?
C5 C6 1.5456(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C10 1.5343(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.5339(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5347(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 1.0000 . ?
C11 C16 1.391(2) . ?
C11 C12 1.4041(18) . ?
C12 C13 1.3924(19) . ?
C12 H12 0.9500 . ?
C13 O1 1.3732(16) . ?
C13 C14 1.393(2) . ?
C14 O2 1.3788(16) . ?
C14 C15 1.395(2) . ?
C15 O3 1.3679(18) . ?
C15 C16 1.3940(18) . ?
C16 H16 0.9500 . ?
C17 O1 1.423(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O2 1.410(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O3 1.4255(18) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.3942(19) . ?
C20 C25 1.3996(19) . ?
C21 C22 1.3974(19) . ?
C21 H21 0.9500 . ?
C22 O4 1.3702(17) . ?
C22 C23 1.391(2) . ?
C23 O5 1.3820(16) . ?
C23 C24 1.395(2) . ?
C24 O6 1.3687(17) . ?
C24 C25 1.391(2) . ?
C25 H25 0.9500 . ?
C26 O4 1.4259(18) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 O5 1.422(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 O6 1.425(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.3927(18) . ?
C29 C34 1.3996(19) . ?
C30 C31 1.3975(18) . ?
C30 H30 0.9500 . ?
C31 O7 1.3707(16) . ?
C31 C32 1.393(2) . ?
C32 O8 1.3873(16) . ?
C32 C33 1.399(2) . ?
C33 O9 1.3722(17) . ?
C33 C34 1.3963(18) . ?
C34 H34 0.9500 . ?
C35 O7 1.4286(18) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 O8 1.4237(17) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 O9 1.4302(19) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C1A C2A 1.423(10) . ?
C1A O1A 1.46(2) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
O1A H1AO 0.8400 . ?
O1B H1BA 0.93(13) . ?
O1B H1BB 0.90(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C2 108.09(10) . . ?
C11 C1 C7 111.69(10) . . ?
C2 C1 C7 108.47(10) . . ?
C11 C1 C6 112.01(10) . . ?
C2 C1 C6 108.52(10) . . ?
C7 C1 C6 107.96(10) . . ?
C3 C2 C1 111.62(10) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C20 C3 C8 113.02(10) . . ?
C20 C3 C2 108.66(10) . . ?
C8 C3 C2 108.29(10) . . ?
C20 C3 C4 109.93(10) . . ?
C8 C3 C4 108.15(10) . . ?
C2 C3 C4 108.70(10) . . ?
C5 C4 C3 111.93(10) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C29 C5 C9 111.38(10) . . ?
C29 C5 C4 111.66(10) . . ?
C9 C5 C4 108.74(10) . . ?
C29 C5 C6 108.54(10) . . ?
C9 C5 C6 108.89(10) . . ?
C4 C5 C6 107.53(10) . . ?
C1 C6 C5 111.88(10) . . ?
C1 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C1 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C10 C7 C1 110.03(10) . . ?
C10 C7 H7A 109.7 . . ?
C1 C7 H7A 109.7 . . ?
C10 C7 H7B 109.7 . . ?
C1 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C10 C8 C3 110.15(10) . . ?
C10 C8 H8A 109.6 . . ?
C3 C8 H8A 109.6 . . ?
C10 C8 H8B 109.6 . . ?
C3 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C5 109.66(10) . . ?
C10 C9 H9A 109.7 . . ?
C5 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C5 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C8 C10 C7 110.36(10) . . ?
C8 C10 C9 109.81(10) . . ?
C7 C10 C9 109.57(10) . . ?
C8 C10 H10 109.0 . . ?
C7 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C16 C11 C12 118.97(12) . . ?
C16 C11 C1 121.29(11) . . ?
C12 C11 C1 119.63(12) . . ?
C13 C12 C11 120.23(13) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
O1 C13 C12 124.35(14) . . ?
O1 C13 C14 115.10(12) . . ?
C12 C13 C14 120.55(12) . . ?
O2 C14 C13 120.08(12) . . ?
O2 C14 C15 120.65(13) . . ?
C13 C14 C15 119.23(12) . . ?
O3 C15 C16 124.03(12) . . ?
O3 C15 C14 115.65(12) . . ?
C16 C15 C14 120.31(13) . . ?
C11 C16 C15 120.66(12) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 119.07(12) . . ?
C21 C20 C3 121.90(12) . . ?
C25 C20 C3 119.01(11) . . ?
C20 C21 C22 120.49(12) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
O4 C22 C23 115.41(12) . . ?
O4 C22 C21 124.43(12) . . ?
C23 C22 C21 120.15(12) . . ?
O5 C23 C22 119.95(12) . . ?
O5 C23 C24 120.54(12) . . ?
C22 C23 C24 119.47(13) . . ?
O6 C24 C25 124.50(13) . . ?
O6 C24 C23 115.11(12) . . ?
C25 C24 C23 120.39(13) . . ?
C24 C25 C20 120.37(13) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O5 C27 H27A 109.5 . . ?
O5 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O5 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O6 C28 H28A 109.5 . . ?
O6 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O6 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C34 118.66(12) . . ?
C30 C29 C5 121.31(11) . . ?
C34 C29 C5 119.99(11) . . ?
C29 C30 C31 120.98(12) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 H30 119.5 . . ?
O7 C31 C32 116.09(11) . . ?
O7 C31 C30 123.47(12) . . ?
C32 C31 C30 120.43(12) . . ?
O8 C32 C31 121.80(12) . . ?
O8 C32 C33 119.37(12) . . ?
C31 C32 C33 118.71(12) . . ?
O9 C33 C34 124.18(12) . . ?
O9 C33 C32 115.01(11) . . ?
C34 C33 C32 120.79(13) . . ?
C33 C34 C29 120.37(12) . . ?
C33 C34 H34 119.8 . . ?
C29 C34 H34 119.8 . . ?
O7 C35 H35A 109.5 . . ?
O7 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O7 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O8 C36 H36A 109.5 . . ?
O8 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O8 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O9 C37 H37A 109.5 . . ?
O9 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O9 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C13 O1 C17 117.62(12) . . ?
C14 O2 C18 113.45(12) . . ?
C15 O3 C19 117.56(11) . . ?
C22 O4 C26 117.22(11) . . ?
C23 O5 C27 113.17(12) . . ?
C24 O6 C28 116.79(12) . . ?
C31 O7 C35 116.87(10) . . ?
C32 O8 C36 114.76(11) . . ?
C33 O9 C37 116.67(11) . . ?
C2A C1A O1A 126.3(11) . . ?
C2A C1A H1AA 105.7 . . ?
O1A C1A H1AA 105.7 . . ?
C2A C1A H1AB 105.7 . . ?
O1A C1A H1AB 105.7 . . ?
H1AA C1A H1AB 106.2 . . ?
C1A C2A H2AA 109.5 . . ?
C1A C2A H2AB 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
C1A C2A H2AC 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
C1A O1A H1AO 109.5 . . ?
H1BA O1B H1BB 98(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
C11 C1 C2 C3 -179.48(10) . . . . ?
C7 C1 C2 C3 59.26(13) . . . . ?
C6 C1 C2 C3 -57.79(13) . . . . ?
C1 C2 C3 C20 177.31(10) . . . . ?
C1 C2 C3 C8 -59.57(13) . . . . ?
C1 C2 C3 C4 57.70(13) . . . . ?
C20 C3 C4 C5 -177.65(10) . . . . ?
C8 C3 C4 C5 58.52(13) . . . . ?
C2 C3 C4 C5 -58.84(13) . . . . ?
C3 C4 C5 C29 178.09(10) . . . . ?
C3 C4 C5 C9 -58.62(13) . . . . ?
C3 C4 C5 C6 59.13(13) . . . . ?
C11 C1 C6 C5 178.23(10) . . . . ?
C2 C1 C6 C5 58.98(13) . . . . ?
C7 C1 C6 C5 -58.39(13) . . . . ?
C29 C5 C6 C1 179.76(10) . . . . ?
C9 C5 C6 C1 58.35(13) . . . . ?
C4 C5 C6 C1 -59.31(13) . . . . ?
C11 C1 C7 C10 -177.09(10) . . . . ?
C2 C1 C7 C10 -58.06(13) . . . . ?
C6 C1 C7 C10 59.34(13) . . . . ?
C20 C3 C8 C10 179.24(10) . . . . ?
C2 C3 C8 C10 58.81(13) . . . . ?
C4 C3 C8 C10 -58.82(13) . . . . ?
C29 C5 C9 C10 -178.06(10) . . . . ?
C4 C5 C9 C10 58.49(13) . . . . ?
C6 C5 C9 C10 -58.40(13) . . . . ?
C3 C8 C10 C7 -59.84(13) . . . . ?
C3 C8 C10 C9 61.05(13) . . . . ?
C1 C7 C10 C8 59.33(13) . . . . ?
C1 C7 C10 C9 -61.70(13) . . . . ?
C5 C9 C10 C8 -60.50(13) . . . . ?
C5 C9 C10 C7 60.86(13) . . . . ?
C2 C1 C11 C16 109.78(13) . . . . ?
C7 C1 C11 C16 -130.97(12) . . . . ?
C6 C1 C11 C16 -9.72(17) . . . . ?
C2 C1 C11 C12 -66.41(15) . . . . ?
C7 C1 C11 C12 52.83(16) . . . . ?
C6 C1 C11 C12 174.08(11) . . . . ?
C16 C11 C12 C13 0.9(2) . . . . ?
C1 C11 C12 C13 177.18(12) . . . . ?
C11 C12 C13 O1 179.02(13) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
O1 C13 C14 O2 -2.64(19) . . . . ?
C12 C13 C14 O2 177.29(12) . . . . ?
O1 C13 C14 C15 179.57(12) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
O2 C14 C15 O3 4.93(18) . . . . ?
C13 C14 C15 O3 -177.29(12) . . . . ?
O2 C14 C15 C16 -175.86(12) . . . . ?
C13 C14 C15 C16 1.9(2) . . . . ?
C12 C11 C16 C15 0.52(19) . . . . ?
C1 C11 C16 C15 -175.70(12) . . . . ?
O3 C15 C16 C11 177.20(12) . . . . ?
C14 C15 C16 C11 -1.9(2) . . . . ?
C8 C3 C20 C21 -11.24(16) . . . . ?
C2 C3 C20 C21 108.98(13) . . . . ?
C4 C3 C20 C21 -132.18(12) . . . . ?
C8 C3 C20 C25 170.63(11) . . . . ?
C2 C3 C20 C25 -69.15(14) . . . . ?
C4 C3 C20 C25 49.69(15) . . . . ?
C25 C20 C21 C22 -0.67(19) . . . . ?
C3 C20 C21 C22 -178.80(11) . . . . ?
C20 C21 C22 O4 179.31(12) . . . . ?
C20 C21 C22 C23 -1.6(2) . . . . ?
O4 C22 C23 O5 4.20(19) . . . . ?
C21 C22 C23 O5 -174.97(12) . . . . ?
O4 C22 C23 C24 -178.08(12) . . . . ?
C21 C22 C23 C24 2.8(2) . . . . ?
O5 C23 C24 O6 -3.62(19) . . . . ?
C22 C23 C24 O6 178.68(12) . . . . ?
O5 C23 C24 C25 176.05(13) . . . . ?
C22 C23 C24 C25 -1.7(2) . . . . ?
O6 C24 C25 C20 179.02(13) . . . . ?
C23 C24 C25 C20 -0.6(2) . . . . ?
C21 C20 C25 C24 1.8(2) . . . . ?
C3 C20 C25 C24 179.96(12) . . . . ?
C9 C5 C29 C30 -128.58(12) . . . . ?
C4 C5 C29 C30 -6.80(16) . . . . ?
C6 C5 C29 C30 111.56(13) . . . . ?
C9 C5 C29 C34 53.96(15) . . . . ?
C4 C5 C29 C34 175.73(11) . . . . ?
C6 C5 C29 C34 -65.91(15) . . . . ?
C34 C29 C30 C31 2.01(19) . . . . ?
C5 C29 C30 C31 -175.49(11) . . . . ?
C29 C30 C31 O7 179.33(12) . . . . ?
C29 C30 C31 C32 -0.60(19) . . . . ?
O7 C31 C32 O8 -5.44(19) . . . . ?
C30 C31 C32 O8 174.49(12) . . . . ?
O7 C31 C32 C33 178.45(11) . . . . ?
C30 C31 C32 C33 -1.62(19) . . . . ?
O8 C32 C33 O9 4.66(18) . . . . ?
C31 C32 C33 O9 -179.13(12) . . . . ?
O8 C32 C33 C34 -173.78(12) . . . . ?
C31 C32 C33 C34 2.4(2) . . . . ?
O9 C33 C34 C29 -179.32(12) . . . . ?
C32 C33 C34 C29 -1.0(2) . . . . ?
C30 C29 C34 C33 -1.19(19) . . . . ?
C5 C29 C34 C33 176.34(11) . . . . ?
C12 C13 O1 C17 0.2(2) . . . . ?
C14 C13 O1 C17 -179.85(14) . . . . ?
C13 C14 O2 C18 94.2(2) . . . . ?
C15 C14 O2 C18 -88.1(2) . . . . ?
C16 C15 O3 C19 7.77(19) . . . . ?
C14 C15 O3 C19 -173.06(12) . . . . ?
C23 C22 O4 C26 172.38(12) . . . . ?
C21 C22 O4 C26 -8.5(2) . . . . ?
C22 C23 O5 C27 -97.15(16) . . . . ?
C24 C23 O5 C27 85.16(17) . . . . ?
C25 C24 O6 C28 -3.7(2) . . . . ?
C23 C24 O6 C28 176.00(16) . . . . ?
C32 C31 O7 C35 173.15(12) . . . . ?
C30 C31 O7 C35 -6.78(18) . . . . ?
C31 C32 O8 C36 73.33(17) . . . . ?
C33 C32 O8 C36 -110.58(14) . . . . ?
C34 C33 O9 C37 -7.2(2) . . . . ?
C32 C33 O9 C37 174.37(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
O1A H1AO O5 0.84 1.99 2.818(4) 166.8 2_565
O1B H1BA O2 0.93(13) 2.53(12) 3.408(5) 158(9) 1_465
O1B H1BA O3 0.93(13) 2.34(12) 3.055(5) 133(8) 1_465
O1B H1BB O1A 0.90(10) 2.10(10) 2.943(7) 156(7) 1_565

_refine_diff_density_max         0.559
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1575312'
_audit_update_record             
;
2017-09-19 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_2b                  
;
PROBLEM: _diffrn_measured_fraction_theta_full Low 
.......      0.959
RESPONSE: Data were collected from a weakly 
diffracting crystal.
Although repeated recrystallization and data 
collection were attempted, but this structure 
represents the best of all.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45.31 H57.63 F6 N O9.77 P'
_chemical_formula_weight         917.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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                   9.6535(16)
_cell_length_b                   12.475(2)
_cell_length_c                   18.922(3)
_cell_angle_alpha                83.815(6)
_cell_angle_beta                 84.842(6)
_cell_angle_gamma                76.722(6)
_cell_volume                     2199.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      4.17
_cell_measurement_theta_max      77.75

_exptl_crystal_description       prismatic
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             967
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.284
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8622
_exptl_absorpt_correction_T_max  0.9447
_exptl_absorpt_process_details   'SADBS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            28079
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.655
_diffrn_reflns_theta_max         79.068
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             8645
_reflns_number_gt                7306
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0614P)²+1.2763P] 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         8645
_refine_ls_number_parameters     610
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1361
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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
C1 C 0.57395(19) 0.47248(15) 0.20191(9) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.52997(19) 0.54046(14) 0.26744(9) 0.0184(4) Uani 1 1 d . . . . .
H2A H 0.450212 0.515173 0.295735 0.022 Uiso 1 1 calc R U . . .
H2B H 0.611410 0.526905 0.297973 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4837(2) 0.66548(15) 0.24564(9) 0.0189(4) Uani 1 1 d . . . . .
C4 C 0.3577(2) 0.68364(15) 0.19839(10) 0.0213(4) Uani 1 1 d . . . . .
H4A H 0.326126 0.763443 0.183348 0.026 Uiso 1 1 calc R U . . .
H4B H 0.276837 0.658711 0.225839 0.026 Uiso 1 1 calc R U . . .
C5 C 0.4017(2) 0.61885(16) 0.13231(10) 0.0226(4) Uani 1 1 d . . . . .
H5 H 0.318451 0.632181 0.102127 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5253(2) 0.65866(16) 0.08878(10) 0.0230(4) Uani 1 1 d . . . . .
H6A H 0.495303 0.738530 0.073578 0.028 Uiso 1 1 calc R U . . .
H6B H 0.551709 0.618285 0.045553 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6551(2) 0.63835(15) 0.13429(9) 0.0202(4) Uani 1 1 d . . . . .
C8 C 0.6986(2) 0.51397(15) 0.15920(9) 0.0196(4) Uani 1 1 d . . . . .
H8A H 0.780513 0.501006 0.189352 0.023 Uiso 1 1 calc R U . . .
H8B H 0.729166 0.471366 0.117132 0.023 Uiso 1 1 calc R U . . .
C9 C 0.4466(2) 0.49524(16) 0.15471(10) 0.0219(4) Uani 1 1 d . . . . .
H9A H 0.473692 0.454021 0.111862 0.026 Uiso 1 1 calc R U . . .
H9B H 0.365620 0.469375 0.181377 0.026 Uiso 1 1 calc R U . . .
C10 C 0.6100(2) 0.70311(15) 0.20109(9) 0.0194(4) Uani 1 1 d . . . . .
H10A H 0.581653 0.783168 0.186098 0.023 Uiso 1 1 calc R U . . .
H10B H 0.692210 0.691245 0.230957 0.023 Uiso 1 1 calc R U . . .
C11 C 0.6153(2) 0.34981(15) 0.22779(9) 0.0200(4) Uani 1 1 d . . . . .
C12 C 0.7549(2) 0.28836(15) 0.21951(10) 0.0217(4) Uani 1 1 d . . . . .
H12 H 0.827104 0.322340 0.196063 0.026 Uiso 1 1 calc R U . . .
C13 C 0.7891(2) 0.17723(16) 0.24548(10) 0.0223(4) Uani 1 1 d . . . . .
C14 C 0.6835(2) 0.12557(15) 0.27953(10) 0.0224(4) Uani 1 1 d . . . . .
C15 C 0.5440(2) 0.18692(16) 0.28782(10) 0.0223(4) Uani 1 1 d . . . . .
C16 C 0.5096(2) 0.29774(15) 0.26252(10) 0.0213(4) Uani 1 1 d . . . . .
H16 H 0.414122 0.338800 0.268643 0.026 Uiso 1 1 calc R U . . .
C17 C 1.0351(2) 0.16082(19) 0.20792(12) 0.0325(5) Uani 1 1 d . . . . .
H17A H 1.126310 0.106805 0.210675 0.049 Uiso 1 1 calc R U . . .
H17B H 1.039098 0.225408 0.232268 0.049 Uiso 1 1 calc R U . . .
H17C H 1.016629 0.183935 0.157851 0.049 Uiso 1 1 calc R U . . .
C18 C 0.6681(3) -0.05849(17) 0.27100(12) 0.0346(5) Uani 1 1 d . . . . .
H18A H 0.565930 -0.050328 0.284028 0.052 Uiso 1 1 calc R U . . .
H18B H 0.718533 -0.134378 0.284983 0.052 Uiso 1 1 calc R U . . .
H18C H 0.683077 -0.042517 0.219379 0.052 Uiso 1 1 calc R U . . .
C19 C 0.3057(2) 0.1891(2) 0.33341(13) 0.0365(5) Uani 1 1 d . . . . .
H19A H 0.301991 0.247276 0.364919 0.055 Uiso 1 1 calc R U . . .
H19B H 0.246728 0.138535 0.355295 0.055 Uiso 1 1 calc R U . . .
H19C H 0.269543 0.222690 0.287511 0.055 Uiso 1 1 calc R U . . .
C20 C 0.4447(2) 0.72727(14) 0.31333(9) 0.0187(4) Uani 1 1 d . . . . .
C21 C 0.5470(2) 0.71907(15) 0.36262(9) 0.0189(4) Uani 1 1 d . . . . .
H21 H 0.640435 0.675707 0.353864 0.023 Uiso 1 1 calc R U . . .
C22 C 0.5133(2) 0.77397(14) 0.42469(9) 0.0193(4) Uani 1 1 d . . . . .
C23 C 0.3757(2) 0.83574(15) 0.43960(9) 0.0203(4) Uani 1 1 d . . . . .
C24 C 0.2733(2) 0.84200(15) 0.39150(10) 0.0219(4) Uani 1 1 d . . . . .
C25 C 0.3077(2) 0.78931(15) 0.32828(10) 0.0215(4) Uani 1 1 d . . . . .
H25 H 0.236773 0.796061 0.295374 0.026 Uiso 1 1 calc R U . . .
C26 C 0.7521(2) 0.72114(18) 0.45839(11) 0.0281(4) Uani 1 1 d . . . . .
H26A H 0.785198 0.758167 0.413883 0.042 Uiso 1 1 calc R U . . .
H26B H 0.761582 0.642598 0.452623 0.042 Uiso 1 1 calc R U . . .
H26C H 0.809815 0.728562 0.496879 0.042 Uiso 1 1 calc R U . . .
C27 C 0.3178(3) 0.99970(16) 0.50010(12) 0.0317(5) Uani 1 1 d . . . . .
H27A H 0.320810 1.023055 0.547648 0.048 Uiso 1 1 calc R U . . .
H27B H 0.223991 1.032400 0.481934 0.048 Uiso 1 1 calc R U . . .
H27C H 0.391868 1.024440 0.467911 0.048 Uiso 1 1 calc R U . . .
C28 C 0.0294(2) 0.90750(19) 0.36457(12) 0.0317(5) Uani 1 1 d . . . . .
H28A H -0.061370 0.948171 0.385575 0.048 Uiso 1 1 calc R U . . .
H28B H 0.020854 0.833039 0.356607 0.048 Uiso 1 1 calc R U . . .
H28C H 0.053575 0.946623 0.319037 0.048 Uiso 1 1 calc R U . . .
C29 C 0.7816(2) 0.67286(15) 0.08980(9) 0.0207(4) Uani 1 1 d . . . . .
C30 C 0.8221(2) 0.63228(16) 0.02287(10) 0.0233(4) Uani 1 1 d . . . . .
H30 H 0.771433 0.584095 0.006305 0.028 Uiso 1 1 calc R U . . .
C31 C 0.9353(2) 0.66154(18) -0.01951(10) 0.0270(4) Uani 1 1 d . . . . .
C32 C 1.0115(3) 0.7322(2) 0.00439(12) 0.0370(5) Uani 1 1 d . . . . .
C33 C 0.9745(2) 0.76959(19) 0.07192(11) 0.0327(5) Uani 1 1 d . . . . .
C34 C 0.8594(2) 0.74132(17) 0.11402(10) 0.0253(4) Uani 1 1 d . . . . .
H34 H 0.834085 0.768889 0.159394 0.030 Uiso 1 1 calc R U . . .
C35 C 0.9001(2) 0.5601(2) -0.11408(11) 0.0342(5) Uani 1 1 d . . . . .
H35A H 0.800138 0.599738 -0.116171 0.051 Uiso 1 1 calc R U . . .
H35B H 0.905692 0.491103 -0.083239 0.051 Uiso 1 1 calc R U . . .
H35C H 0.940058 0.543201 -0.162115 0.051 Uiso 1 1 calc R U . . .
C36A C 1.2460(4) 0.7396(3) -0.03407(18) 0.0374(11) Uani 0.649(7) 1 d . . P A 1
H36A H 1.266324 0.769314 0.008778 0.045 Uiso 0.649(7) 1 calc R U P A 1
H36B H 1.305867 0.762659 -0.074837 0.045 Uiso 0.649(7) 1 calc R U P A 1
H36C H 1.266571 0.658640 -0.026903 0.045 Uiso 0.649(7) 1 calc R U P A 1
C36B C 1.1626(10) 0.8440(7) -0.0456(4) 0.055(3) Uani 0.351(7) 1 d . . P A 2
H36D H 1.071077 0.890838 -0.059341 0.066 Uiso 0.351(7) 1 calc R U P A 2
H36E H 1.234603 0.846018 -0.085356 0.066 Uiso 0.351(7) 1 calc R U P A 2
H36F H 1.192582 0.871449 -0.004135 0.066 Uiso 0.351(7) 1 calc R U P A 2
C37 C 1.0210(3) 0.8797(2) 0.15916(14) 0.0424(6) Uani 1 1 d . . . . .
H37A H 1.016620 0.819776 0.196704 0.064 Uiso 1 1 calc R U . . .
H37B H 0.927812 0.931490 0.157865 0.064 Uiso 1 1 calc R U . . .
H37C H 1.093359 0.918826 0.169031 0.064 Uiso 1 1 calc R U . . .
O1 O 0.92310(15) 0.11170(11) 0.24142(8) 0.0289(3) Uani 1 1 d . . . . .
O2 O 0.72212(16) 0.01716(11) 0.30696(8) 0.0280(3) Uani 1 1 d . . . . .
O3 O 0.44870(15) 0.12966(11) 0.32255(8) 0.0280(3) Uani 1 1 d . . . . .
O4 O 0.60686(14) 0.77052(11) 0.47548(7) 0.0235(3) Uani 1 1 d . . . . .
O5 O 0.34211(15) 0.88170(11) 0.50420(7) 0.0238(3) Uani 1 1 d . . . . .
O6 O 0.13907(15) 0.89976(12) 0.41190(7) 0.0289(3) Uani 1 1 d . . . . .
O7 O 0.97934(16) 0.62756(14) -0.08596(7) 0.0335(4) Uani 1 1 d . . . . .
O8A O 1.0995(4) 0.7804(3) -0.04752(17) 0.0361(9) Uani 0.649(7) 1 d . . P A 1
O8B O 1.1473(7) 0.7339(6) -0.0281(3) 0.0309(16) Uani 0.351(7) 1 d . . P A 2
O9 O 1.0575(2) 0.83494(17) 0.09233(10) 0.0530(5) Uani 1 1 d . . . . .
C38 C 0.5635(2) 0.45826(15) 0.48834(9) 0.0215(4) Uani 1 1 d . . . . .
C39 C 0.6914(2) 0.43866(17) 0.52169(10) 0.0254(4) Uani 1 1 d . . . . .
H39 H 0.698323 0.479369 0.560364 0.030 Uiso 1 1 calc R U . . .
C40 C 0.8067(2) 0.36097(17) 0.49884(10) 0.0270(4) Uani 1 1 d . . . . .
H40 H 0.893039 0.348149 0.522056 0.032 Uiso 1 1 calc R U . . .
C41 C 0.6789(2) 0.31866(16) 0.41068(10) 0.0250(4) Uani 1 1 d . . . . .
H41 H 0.675187 0.276904 0.372047 0.030 Uiso 1 1 calc R U . . .
C42 C 0.5606(2) 0.39504(16) 0.43191(10) 0.0238(4) Uani 1 1 d . . . . .
H42 H 0.475461 0.405285 0.408038 0.029 Uiso 1 1 calc R U . . .
C43 C 0.9238(2) 0.21576(18) 0.42189(11) 0.0292(4) Uani 1 1 d . . . . .
H43A H 0.903737 0.185862 0.379052 0.044 Uiso 1 1 calc R U . . .
H43B H 0.942125 0.156224 0.460411 0.044 Uiso 1 1 calc R U . . .
H43C H 1.007896 0.247840 0.411663 0.044 Uiso 1 1 calc R U . . .
N1 N 0.79980(18) 0.30224(13) 0.44381(8) 0.0231(3) Uani 1 1 d . . . . .
F1 F 0.20277(14) 0.48629(13) 0.32301(9) 0.0479(4) Uani 1 1 d . . . . .
F2 F 0.0116(2) 0.57443(13) 0.26188(7) 0.0567(4) Uani 1 1 d . . . . .
F3 F -0.13482(14) 0.52078(13) 0.35273(8) 0.0467(4) Uani 1 1 d . . . . .
F4 F 0.05600(16) 0.43578(12) 0.41230(7) 0.0444(3) Uani 1 1 d . . . . .
F5 F 0.03703(15) 0.39355(11) 0.30080(7) 0.0385(3) Uani 1 1 d . . . . .
F6 F 0.03091(14) 0.61576(11) 0.37305(7) 0.0382(3) Uani 1 1 d . . . . .
P1 P 0.03356(5) 0.50525(4) 0.33636(2) 0.02346(13) Uani 1 1 d . . . . .
C44 C 0.4082(6) 0.1470(4) 0.1056(3) 0.0778(15) Uani 0.773(5) 1 d . . P . .
H44A H 0.481847 0.162367 0.069313 0.117 Uiso 0.773(5) 1 calc R U P . .
H44B H 0.445062 0.139460 0.152960 0.117 Uiso 0.773(5) 1 calc R U P . .
H44C H 0.323855 0.208082 0.102971 0.117 Uiso 0.773(5) 1 calc R U P . .
C45 C 0.3688(5) 0.0428(4) 0.0931(2) 0.0658(12) Uani 0.773(5) 1 d . . P . .
C46 C 0.2944(6) 0.0391(5) 0.0293(3) 0.0886(17) Uani 0.773(5) 1 d . . P . .
H46A H 0.359254 0.044194 -0.013228 0.133 Uiso 0.773(5) 1 calc R U P . .
H46B H 0.211265 0.101181 0.026276 0.133 Uiso 0.773(5) 1 calc R U P . .
H46C H 0.262887 -0.030695 0.032260 0.133 Uiso 0.773(5) 1 calc R U P . .
O10 O 0.3818(6) -0.0328(4) 0.1360(3) 0.148(2) Uani 0.773(5) 1 d . . P . .


_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
C1 C11 1.528(3) . ?
C1 C9 1.540(2) . ?
C1 C8 1.546(2) . ?
C1 C2 1.550(2) . ?
C2 C3 1.542(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.535(2) . ?
C3 C20 1.539(2) . ?
C3 C10 1.552(2) . ?
C4 C5 1.537(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C9 1.527(3) . ?
C5 C6 1.535(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.542(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C29 1.538(2) . ?
C7 C8 1.544(3) . ?
C7 C10 1.549(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.393(3) . ?
C11 C16 1.409(2) . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 O1 1.363(2) . ?
C13 C14 1.401(3) . ?
C14 O2 1.375(2) . ?
C14 C15 1.392(3) . ?
C15 O3 1.372(2) . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
C17 O1 1.429(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O2 1.433(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O3 1.418(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.392(3) . ?
C20 C21 1.398(3) . ?
C21 C22 1.399(2) . ?
C21 H21 0.9500 . ?
C22 O4 1.368(2) . ?
C22 C23 1.395(3) . ?
C23 C24 1.387(3) . ?
C23 O5 1.387(2) . ?
C24 O6 1.374(2) . ?
C24 C25 1.404(3) . ?
C25 H25 0.9500 . ?
C26 O4 1.419(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 O5 1.431(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 O6 1.427(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C34 1.394(3) . ?
C29 C30 1.404(3) . ?
C30 C31 1.390(3) . ?
C30 H30 0.9500 . ?
C31 O7 1.370(2) . ?
C31 C32 1.402(3) . ?
C32 C33 1.396(3) . ?
C32 O8B 1.401(5) . ?
C32 O8A 1.416(4) . ?
C33 O9 1.371(2) . ?
C33 C34 1.398(3) . ?
C34 H34 0.9500 . ?
C35 O7 1.429(2) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36A O8A 1.425(6) . ?
C36A H36A 0.9800 . ?
C36A H36B 0.9800 . ?
C36A H36C 0.9800 . ?
C36B O8B 1.415(10) . ?
C36B H36D 0.9800 . ?
C36B H36E 0.9800 . ?
C36B H36F 0.9800 . ?
C37 O9 1.420(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C39 1.397(3) . ?
C38 C42 1.400(2) . ?
C38 C38 1.482(4) 2_666 ?
C39 C40 1.369(3) . ?
C39 H39 0.9500 . ?
C40 N1 1.351(2) . ?
C40 H40 0.9500 . ?
C41 N1 1.338(3) . ?
C41 C42 1.369(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 N1 1.478(3) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
F1 P1 1.5966(14) . ?
F2 P1 1.5759(15) . ?
F3 P1 1.5979(14) . ?
F4 P1 1.6014(14) . ?
F5 P1 1.6039(13) . ?
F6 P1 1.6032(13) . ?
C44 C45 1.484(6) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 O10 1.168(5) . ?
C45 C46 1.469(7) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C9 110.61(14) . . ?
C11 C1 C8 112.37(15) . . ?
C9 C1 C8 108.60(14) . . ?
C11 C1 C2 108.89(14) . . ?
C9 C1 C2 108.52(15) . . ?
C8 C1 C2 107.73(13) . . ?
C3 C2 C1 112.08(14) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C20 112.39(15) . . ?
C4 C3 C2 107.89(14) . . ?
C20 C3 C2 108.98(14) . . ?
C4 C3 C10 108.65(14) . . ?
C20 C3 C10 110.54(13) . . ?
C2 C3 C10 108.28(15) . . ?
C3 C4 C5 110.25(15) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C9 C5 C6 109.89(16) . . ?
C9 C5 C4 110.14(15) . . ?
C6 C5 C4 109.84(14) . . ?
C9 C5 H5 109.0 . . ?
C6 C5 H5 109.0 . . ?
C4 C5 H5 109.0 . . ?
C5 C6 C7 109.81(15) . . ?
C5 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C29 C7 C6 110.02(14) . . ?
C29 C7 C8 108.76(15) . . ?
C6 C7 C8 109.19(14) . . ?
C29 C7 C10 112.40(14) . . ?
C6 C7 C10 108.18(15) . . ?
C8 C7 C10 108.24(14) . . ?
C7 C8 C1 111.54(15) . . ?
C7 C8 H8A 109.3 . . ?
C1 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C1 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C5 C9 C1 110.06(14) . . ?
C5 C9 H9A 109.6 . . ?
C1 C9 H9A 109.6 . . ?
C5 C9 H9B 109.6 . . ?
C1 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
C7 C10 C3 111.37(14) . . ?
C7 C10 H10A 109.4 . . ?
C3 C10 H10A 109.4 . . ?
C7 C10 H10B 109.4 . . ?
C3 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C16 118.94(17) . . ?
C12 C11 C1 122.05(16) . . ?
C16 C11 C1 119.00(17) . . ?
C11 C12 C13 120.33(17) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
O1 C13 C12 124.32(17) . . ?
O1 C13 C14 115.12(17) . . ?
C12 C13 C14 120.55(18) . . ?
O2 C14 C15 121.85(17) . . ?
O2 C14 C13 118.93(18) . . ?
C15 C14 C13 119.14(17) . . ?
O3 C15 C16 124.54(18) . . ?
O3 C15 C14 114.91(17) . . ?
C16 C15 C14 120.54(17) . . ?
C15 C16 C11 120.49(18) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 118.41(16) . . ?
C25 C20 C3 121.66(16) . . ?
C21 C20 C3 119.91(16) . . ?
C20 C21 C22 120.76(17) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
O4 C22 C23 114.85(15) . . ?
O4 C22 C21 124.49(17) . . ?
C23 C22 C21 120.64(17) . . ?
C24 C23 O5 121.74(17) . . ?
C24 C23 C22 118.65(16) . . ?
O5 C23 C22 119.40(16) . . ?
O6 C24 C23 114.93(16) . . ?
O6 C24 C25 124.20(17) . . ?
C23 C24 C25 120.84(17) . . ?
C20 C25 C24 120.66(17) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O5 C27 H27A 109.5 . . ?
O5 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O5 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O6 C28 H28A 109.5 . . ?
O6 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O6 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C34 C29 C30 118.72(17) . . ?
C34 C29 C7 122.44(16) . . ?
C30 C29 C7 118.83(15) . . ?
C31 C30 C29 121.00(17) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
O7 C31 C30 124.57(17) . . ?
O7 C31 C32 115.29(17) . . ?
C30 C31 C32 120.13(18) . . ?
C33 C32 O8B 119.5(3) . . ?
C33 C32 C31 118.95(18) . . ?
O8B C32 C31 118.3(3) . . ?
C33 C32 O8A 122.9(2) . . ?
C31 C32 O8A 116.6(2) . . ?
O9 C33 C32 115.32(18) . . ?
O9 C33 C34 123.90(18) . . ?
C32 C33 C34 120.77(18) . . ?
C29 C34 C33 120.37(18) . . ?
C29 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
O7 C35 H35A 109.5 . . ?
O7 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O7 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O8A C36A H36A 109.5 . . ?
O8A C36A H36B 109.5 . . ?
H36A C36A H36B 109.5 . . ?
O8A C36A H36C 109.5 . . ?
H36A C36A H36C 109.5 . . ?
H36B C36A H36C 109.5 . . ?
O8B C36B H36D 109.5 . . ?
O8B C36B H36E 109.5 . . ?
H36D C36B H36E 109.5 . . ?
O8B C36B H36F 109.5 . . ?
H36D C36B H36F 109.5 . . ?
H36E C36B H36F 109.5 . . ?
O9 C37 H37A 109.5 . . ?
O9 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O9 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C13 O1 C17 117.35(16) . . ?
C14 O2 C18 114.25(16) . . ?
C15 O3 C19 117.02(16) . . ?
C22 O4 C26 116.73(14) . . ?
C23 O5 C27 115.37(14) . . ?
C24 O6 C28 117.10(15) . . ?
C31 O7 C35 117.27(15) . . ?
C32 O8A C36A 110.4(3) . . ?
C32 O8B C36B 110.7(6) . . ?
C33 O9 C37 117.92(17) . . ?
C39 C38 C42 116.84(18) . . ?
C39 C38 C38 121.7(2) . 2_666 ?
C42 C38 C38 121.5(2) . 2_666 ?
C40 C39 C38 120.21(17) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
N1 C40 C39 121.08(18) . . ?
N1 C40 H40 119.5 . . ?
C39 C40 H40 119.5 . . ?
N1 C41 C42 120.64(17) . . ?
N1 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C41 C42 C38 120.88(18) . . ?
C41 C42 H42 119.6 . . ?
C38 C42 H42 119.6 . . ?
N1 C43 H43A 109.5 . . ?
N1 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
N1 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 N1 C40 120.35(18) . . ?
C41 N1 C43 119.48(16) . . ?
C40 N1 C43 120.12(17) . . ?
F2 P1 F1 91.12(10) . . ?
F2 P1 F3 91.29(10) . . ?
F1 P1 F3 177.58(9) . . ?
F2 P1 F4 179.57(8) . . ?
F1 P1 F4 88.83(9) . . ?
F3 P1 F4 88.76(8) . . ?
F2 P1 F6 90.24(8) . . ?
F1 P1 F6 89.49(7) . . ?
F3 P1 F6 90.75(7) . . ?
F4 P1 F6 89.33(8) . . ?
F2 P1 F5 90.66(8) . . ?
F1 P1 F5 90.33(8) . . ?
F3 P1 F5 89.38(7) . . ?
F4 P1 F5 89.77(8) . . ?
F6 P1 F5 179.09(8) . . ?
C45 C44 H44A 109.5 . . ?
C45 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C45 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
O10 C45 C46 118.5(5) . . ?
O10 C45 C44 121.7(5) . . ?
C46 C45 C44 119.3(4) . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 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
C11 C1 C2 C3 -178.89(14) . . . . ?
C9 C1 C2 C3 -58.42(18) . . . . ?
C8 C1 C2 C3 58.99(19) . . . . ?
C1 C2 C3 C4 58.82(18) . . . . ?
C1 C2 C3 C20 -178.89(14) . . . . ?
C1 C2 C3 C10 -58.60(18) . . . . ?
C20 C3 C4 C5 -179.11(14) . . . . ?
C2 C3 C4 C5 -58.95(18) . . . . ?
C10 C3 C4 C5 58.23(19) . . . . ?
C3 C4 C5 C9 60.88(19) . . . . ?
C3 C4 C5 C6 -60.3(2) . . . . ?
C9 C5 C6 C7 -60.40(19) . . . . ?
C4 C5 C6 C7 60.9(2) . . . . ?
C5 C6 C7 C29 177.26(15) . . . . ?
C5 C6 C7 C8 57.97(19) . . . . ?
C5 C6 C7 C10 -59.61(19) . . . . ?
C29 C7 C8 C1 -177.77(14) . . . . ?
C6 C7 C8 C1 -57.71(18) . . . . ?
C10 C7 C8 C1 59.84(18) . . . . ?
C11 C1 C8 C7 -179.34(14) . . . . ?
C9 C1 C8 C7 57.96(18) . . . . ?
C2 C1 C8 C7 -59.39(18) . . . . ?
C6 C5 C9 C1 61.18(18) . . . . ?
C4 C5 C9 C1 -59.96(19) . . . . ?
C11 C1 C9 C5 177.16(14) . . . . ?
C8 C1 C9 C5 -59.09(18) . . . . ?
C2 C1 C9 C5 57.76(18) . . . . ?
C29 C7 C10 C3 -179.12(15) . . . . ?
C6 C7 C10 C3 59.21(19) . . . . ?
C8 C7 C10 C3 -58.98(19) . . . . ?
C4 C3 C10 C7 -58.6(2) . . . . ?
C20 C3 C10 C7 177.63(15) . . . . ?
C2 C3 C10 C7 58.31(19) . . . . ?
C9 C1 C11 C12 128.11(17) . . . . ?
C8 C1 C11 C12 6.6(2) . . . . ?
C2 C1 C11 C12 -112.71(18) . . . . ?
C9 C1 C11 C16 -53.3(2) . . . . ?
C8 C1 C11 C16 -174.85(15) . . . . ?
C2 C1 C11 C16 65.9(2) . . . . ?
C16 C11 C12 C13 -0.2(3) . . . . ?
C1 C11 C12 C13 178.37(16) . . . . ?
C11 C12 C13 O1 -178.21(17) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
O1 C13 C14 O2 1.5(2) . . . . ?
C12 C13 C14 O2 -177.42(16) . . . . ?
O1 C13 C14 C15 178.31(16) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
O2 C14 C15 O3 -2.5(3) . . . . ?
C13 C14 C15 O3 -179.21(16) . . . . ?
O2 C14 C15 C16 176.89(16) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
O3 C15 C16 C11 179.59(16) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
C1 C11 C16 C15 -178.85(16) . . . . ?
C4 C3 C20 C25 1.5(2) . . . . ?
C2 C3 C20 C25 -118.04(18) . . . . ?
C10 C3 C20 C25 123.07(18) . . . . ?
C4 C3 C20 C21 179.54(15) . . . . ?
C2 C3 C20 C21 60.0(2) . . . . ?
C10 C3 C20 C21 -58.9(2) . . . . ?
C25 C20 C21 C22 -1.4(2) . . . . ?
C3 C20 C21 C22 -179.55(15) . . . . ?
C20 C21 C22 O4 -179.85(15) . . . . ?
C20 C21 C22 C23 1.7(3) . . . . ?
O4 C22 C23 C24 -178.87(15) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
O4 C22 C23 O5 -3.9(2) . . . . ?
C21 C22 C23 O5 174.69(15) . . . . ?
O5 C23 C24 O6 2.0(2) . . . . ?
C22 C23 C24 O6 176.87(15) . . . . ?
O5 C23 C24 C25 -176.19(16) . . . . ?
C22 C23 C24 C25 -1.3(3) . . . . ?
C21 C20 C25 C24 -0.2(3) . . . . ?
C3 C20 C25 C24 177.89(16) . . . . ?
O6 C24 C25 C20 -176.44(16) . . . . ?
C23 C24 C25 C20 1.6(3) . . . . ?
C6 C7 C29 C34 130.3(2) . . . . ?
C8 C7 C29 C34 -110.1(2) . . . . ?
C10 C7 C29 C34 9.7(3) . . . . ?
C6 C7 C29 C30 -50.9(2) . . . . ?
C8 C7 C29 C30 68.6(2) . . . . ?
C10 C7 C29 C30 -171.54(17) . . . . ?
C34 C29 C30 C31 -1.6(3) . . . . ?
C7 C29 C30 C31 179.65(19) . . . . ?
C29 C30 C31 O7 -178.48(19) . . . . ?
C29 C30 C31 C32 0.3(3) . . . . ?
O7 C31 C32 C33 -179.3(2) . . . . ?
C30 C31 C32 C33 1.8(4) . . . . ?
O7 C31 C32 O8B -19.8(5) . . . . ?
C30 C31 C32 O8B 161.3(4) . . . . ?
O7 C31 C32 O8A 14.5(4) . . . . ?
C30 C31 C32 O8A -164.4(3) . . . . ?
O8B C32 C33 O9 18.5(5) . . . . ?
C31 C32 C33 O9 177.7(2) . . . . ?
O8A C32 C33 O9 -17.0(4) . . . . ?
O8B C32 C33 C34 -161.9(4) . . . . ?
C31 C32 C33 C34 -2.8(4) . . . . ?
O8A C32 C33 C34 162.6(3) . . . . ?
C30 C29 C34 C33 0.6(3) . . . . ?
C7 C29 C34 C33 179.4(2) . . . . ?
O9 C33 C34 C29 -179.0(2) . . . . ?
C32 C33 C34 C29 1.5(4) . . . . ?
C12 C13 O1 C17 -0.3(3) . . . . ?
C14 C13 O1 C17 -179.26(17) . . . . ?
C15 C14 O2 C18 70.8(2) . . . . ?
C13 C14 O2 C18 -112.5(2) . . . . ?
C16 C15 O3 C19 -0.5(3) . . . . ?
C14 C15 O3 C19 178.93(17) . . . . ?
C23 C22 O4 C26 -171.94(16) . . . . ?
C21 C22 O4 C26 9.5(2) . . . . ?
C24 C23 O5 C27 -74.5(2) . . . . ?
C22 C23 O5 C27 110.70(19) . . . . ?
C23 C24 O6 C28 -179.30(17) . . . . ?
C25 C24 O6 C28 -1.2(3) . . . . ?
C30 C31 O7 C35 2.0(3) . . . . ?
C32 C31 O7 C35 -176.8(2) . . . . ?
C33 C32 O8A C36A 80.8(4) . . . . ?
C31 C32 O8A C36A -113.5(3) . . . . ?
C33 C32 O8B C36B -67.5(7) . . . . ?
C31 C32 O8B C36B 133.2(5) . . . . ?
C32 C33 O9 C37 177.2(2) . . . . ?
C34 C33 O9 C37 -2.4(4) . . . . ?
C42 C38 C39 C40 0.2(3) . . . . ?
C38 C38 C39 C40 -180.0(2) 2_666 . . . ?
C38 C39 C40 N1 0.2(3) . . . . ?
N1 C41 C42 C38 0.5(3) . . . . ?
C39 C38 C42 C41 -0.6(3) . . . . ?
C38 C38 C42 C41 179.6(2) 2_666 . . . ?
C42 C41 N1 C40 0.0(3) . . . . ?
C42 C41 N1 C43 177.26(17) . . . . ?
C39 C40 N1 C41 -0.4(3) . . . . ?
C39 C40 N1 C43 -177.60(18) . . . . ?

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.092

