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

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

data_i568
_database_code_depnum_ccdc_archive 'CCDC 1871419'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C68 H68 Cl6 N4 O10 P2'
_chemical_formula_weight         1375.90

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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

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

_cell_length_a                   25.2081(12)
_cell_length_b                   25.2081(12)
_cell_length_c                   30.1100(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     16570.0(18)
_cell_formula_units_Z            9
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    9796
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      66.65

_exptl_crystal_description       block
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             6444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    2.992
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5816
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45452
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.500
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_full        66.595
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6508
_reflns_number_gt                6020
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_bruker_data_scaling   'SADABS V2018/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2018.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1217P)²+95.1428P] 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         6508
_refine_ls_number_parameters     480
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1949
_refine_ls_wR_factor_gt          0.1913
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.09373(3) 0.33269(3) 0.46406(2) 0.01778(18) Uani 1 1 d . . . . .
O4 O 0.12172(11) 0.19341(11) 0.29653(7) 0.0359(5) Uani 1 1 d . . . . .
O5 O 0.10840(13) 0.19677(17) 0.36650(8) 0.0573(8) Uani 1 1 d . . . . .
N1 N 0.31686(10) 0.35802(10) 0.34390(7) 0.0186(5) Uani 1 1 d . . . . .
N2 N 0.14251(12) 0.20114(13) 0.33516(9) 0.0322(6) Uani 1 1 d . . . . .
O1 O 0.30454(9) 0.34920(10) 0.41891(6) 0.0260(4) Uani 1 1 d . . . . .
O2 O 0.32803(8) 0.36967(9) 0.26894(6) 0.0215(4) Uani 1 1 d . . . . .
O3 O 0.19743(10) 0.21769(11) 0.34198(8) 0.0356(5) Uani 1 1 d . . . . .
C1 C 0.29490(12) 0.35727(12) 0.30144(8) 0.0179(5) Uani 1 1 d . . . . .
C2 C 0.28316(12) 0.34933(13) 0.38277(9) 0.0204(5) Uani 1 1 d . . . . .
C3 C 0.19667(12) 0.33839(12) 0.33494(8) 0.0174(5) Uani 1 1 d . . . . .
C4 C 0.22168(12) 0.34241(12) 0.37747(8) 0.0180(5) Uani 1 1 d . . . . .
C5 C 0.18933(12) 0.34009(12) 0.41481(8) 0.0195(5) Uani 1 1 d . . . . .
H5 H 0.207458 0.344290 0.443205 0.023 Uiso 1 1 calc R U . . .
C6 C 0.12978(12) 0.33161(12) 0.41190(8) 0.0180(5) Uani 1 1 d . . . . .
C7 C 0.10285(12) 0.32403(12) 0.37011(8) 0.0177(5) Uani 1 1 d . . . . .
C8 C 0.38086(12) 0.37214(13) 0.34900(9) 0.0217(6) Uani 1 1 d D . . . .
H8A H 0.3981(14) 0.3992(13) 0.3749(7) 0.026 Uiso 1 1 d D U . . .
H8B H 0.4044(13) 0.4016(12) 0.3256(8) 0.026 Uiso 1 1 d D U . . .
C9 C 0.3853(2) 0.3141(2) 0.3602(2) 0.0292(10) Uani 0.662(5) 1 d D U P A 1
H9 H 0.362244 0.296039 0.388325 0.035 Uiso 0.662(5) 1 calc R U P A 1
C10 C 0.3566(2) 0.2657(2) 0.32372(17) 0.0339(11) Uani 0.662(5) 1 d D U P A 1
H10A H 0.316191 0.260517 0.315821 0.041 Uiso 0.662(5) 1 calc R U P A 1
H10B H 0.382889 0.280520 0.296948 0.041 Uiso 0.662(5) 1 calc R U P A 1
C11 C 0.3483(4) 0.2035(3) 0.3369(3) 0.0441(18) Uani 0.662(5) 1 d D U P A 1
H11A H 0.329278 0.174579 0.312351 0.066 Uiso 0.662(5) 1 calc R U P A 1
H11B H 0.321899 0.188218 0.363202 0.066 Uiso 0.662(5) 1 calc R U P A 1
H11C H 0.388293 0.207903 0.343718 0.066 Uiso 0.662(5) 1 calc R U P A 1
C12 C 0.4530(2) 0.3338(3) 0.3683(2) 0.0361(11) Uani 0.662(5) 1 d D U P A 1
H12A H 0.456452 0.296505 0.370692 0.043 Uiso 0.662(5) 1 calc R U P A 1
H12B H 0.476958 0.356958 0.342024 0.043 Uiso 0.662(5) 1 calc R U P A 1
C13 C 0.4817(3) 0.3725(3) 0.4090(2) 0.0426(14) Uani 0.662(5) 1 d D U P A 1
H13A H 0.455597 0.351594 0.435050 0.051 Uiso 0.662(5) 1 calc R U P A 1
H13B H 0.482880 0.412111 0.405258 0.051 Uiso 0.662(5) 1 calc R U P A 1
C14 C 0.5460(3) 0.3850(4) 0.4182(3) 0.0567(16) Uani 0.662(5) 1 d D U P A 1
H14A H 0.545314 0.345435 0.420141 0.068 Uiso 0.662(5) 1 calc R U P A 1
H14B H 0.572769 0.408242 0.393010 0.068 Uiso 0.662(5) 1 calc R U P A 1
C15 C 0.5731(4) 0.4206(4) 0.4606(3) 0.071(2) Uani 0.662(5) 1 d D U P A 1
H15A H 0.602542 0.409930 0.472862 0.107 Uiso 0.662(5) 1 calc R U P A 1
H15B H 0.540257 0.410334 0.482243 0.107 Uiso 0.662(5) 1 calc R U P A 1
H15C H 0.593896 0.464589 0.454228 0.107 Uiso 0.662(5) 1 calc R U P A 1
C9X C 0.3927(4) 0.3209(4) 0.3361(4) 0.0259(17) Uani 0.338(5) 1 d D U P A 2
H9X H 0.382331 0.311350 0.303930 0.031 Uiso 0.338(5) 1 calc R U P A 2
C10X C 0.3522(4) 0.2632(4) 0.3629(3) 0.0268(17) Uani 0.338(5) 1 d D U P A 2
H10C H 0.308790 0.251638 0.358591 0.032 Uiso 0.338(5) 1 calc R U P A 2
H10D H 0.361850 0.272205 0.394873 0.032 Uiso 0.338(5) 1 calc R U P A 2
C11X C 0.3602(8) 0.2088(6) 0.3501(5) 0.039(3) Uani 0.338(5) 1 d D U P A 2
H11D H 0.362416 0.206855 0.317672 0.058 Uiso 0.338(5) 1 calc R U P A 2
H11E H 0.325192 0.170769 0.361060 0.058 Uiso 0.338(5) 1 calc R U P A 2
H11F H 0.398015 0.213968 0.363265 0.058 Uiso 0.338(5) 1 calc R U P A 2
C12X C 0.4614(4) 0.3443(5) 0.3419(4) 0.038(2) Uani 0.338(5) 1 d D U P A 2
H12C H 0.469890 0.312022 0.331667 0.045 Uiso 0.338(5) 1 calc R U P A 2
H12D H 0.484281 0.380258 0.322246 0.045 Uiso 0.338(5) 1 calc R U P A 2
C13X C 0.4862(6) 0.3627(8) 0.3889(5) 0.055(3) Uani 0.338(5) 1 d D U P A 2
H13C H 0.462593 0.327510 0.409044 0.066 Uiso 0.338(5) 1 calc R U P A 2
H13D H 0.479831 0.396585 0.398886 0.066 Uiso 0.338(5) 1 calc R U P A 2
C14X C 0.5542(6) 0.3831(9) 0.3928(6) 0.076(3) Uani 0.338(5) 1 d D U P A 2
H14C H 0.576005 0.408807 0.366819 0.091 Uiso 0.338(5) 1 calc R U P A 2
H14D H 0.558897 0.346438 0.392019 0.091 Uiso 0.338(5) 1 calc R U P A 2
C15X C 0.5844(9) 0.4195(10) 0.4354(7) 0.088(4) Uani 0.338(5) 1 d D U P A 2
H15D H 0.627999 0.432047 0.435368 0.133 Uiso 0.338(5) 1 calc R U P A 2
H15E H 0.564547 0.393635 0.461389 0.133 Uiso 0.338(5) 1 calc R U P A 2
H15F H 0.579882 0.455860 0.436590 0.133 Uiso 0.338(5) 1 calc R U P A 2
C16 C 0.04119(13) 0.25621(13) 0.48202(9) 0.0220(6) Uani 1 1 d . . . . .
C17 C 0.02107(13) 0.20679(14) 0.45328(10) 0.0269(6) Uani 1 1 d . . . . .
H17 H 0.033393 0.213241 0.423018 0.032 Uiso 1 1 calc R U . . .
C18 C -0.01703(15) 0.14807(15) 0.46896(12) 0.0356(7) Uani 1 1 d . . . . .
H18 H -0.031742 0.114138 0.449295 0.043 Uiso 1 1 calc R U . . .
C19 C -0.03370(16) 0.13881(17) 0.51334(14) 0.0434(9) Uani 1 1 d . . . . .
H19 H -0.059227 0.098307 0.524007 0.052 Uiso 1 1 calc R U . . .
C20 C -0.01370(17) 0.18773(18) 0.54239(12) 0.0422(9) Uani 1 1 d . . . . .
H20 H -0.025635 0.180834 0.572719 0.051 Uiso 1 1 calc R U . . .
C21 C 0.02384(15) 0.24683(16) 0.52691(10) 0.0320(7) Uani 1 1 d . . . . .
H21 H 0.037720 0.280714 0.546539 0.038 Uiso 1 1 calc R U . . .
C22 C 0.15563(13) 0.36499(14) 0.50400(9) 0.0234(6) Uani 1 1 d . . . . .
C23 C 0.17320(16) 0.32746(16) 0.52604(9) 0.0309(7) Uani 1 1 d . . . . .
H23 H 0.149405 0.284222 0.522972 0.037 Uiso 1 1 calc R U . . .
C24 C 0.22503(18) 0.3530(2) 0.55227(11) 0.0422(9) Uani 1 1 d . . . . .
H24 H 0.237058 0.327264 0.566840 0.051 Uiso 1 1 calc R U . . .
C25 C 0.25920(18) 0.4151(2) 0.55745(13) 0.0492(10) Uani 1 1 d . . . . .
H25 H 0.295051 0.432388 0.575330 0.059 Uiso 1 1 calc R U . . .
C26 C 0.24167(18) 0.4526(2) 0.53677(15) 0.0517(10) Uani 1 1 d . . . . .
H26 H 0.265112 0.495698 0.540877 0.062 Uiso 1 1 calc R U . . .
C27 C 0.19001(15) 0.42791(16) 0.50999(12) 0.0366(7) Uani 1 1 d . . . . .
H27 H 0.178187 0.454033 0.495761 0.044 Uiso 1 1 calc R U . . .
C28 C 0.06298(13) 0.38323(13) 0.46143(8) 0.0207(5) Uani 1 1 d . . . . .
C29 C 0.01168(14) 0.37077(14) 0.48649(9) 0.0256(6) Uani 1 1 d . . . . .
H29 H -0.007296 0.335536 0.504965 0.031 Uiso 1 1 calc R U . . .
C30 C -0.01139(16) 0.41021(16) 0.48421(11) 0.0350(7) Uani 1 1 d . . . . .
H30 H -0.046406 0.402082 0.501221 0.042 Uiso 1 1 calc R U . . .
C31 C 0.01637(18) 0.46161(17) 0.45719(12) 0.0404(8) Uani 1 1 d . . . . .
H31 H -0.000037 0.488244 0.455392 0.048 Uiso 1 1 calc R U . . .
C32 C 0.06817(17) 0.47423(15) 0.43271(11) 0.0364(7) Uani 1 1 d . . . . .
H32 H 0.087414 0.509870 0.414651 0.044 Uiso 1 1 calc R U . . .
C33 C 0.09179(14) 0.43533(14) 0.43449(10) 0.0279(6) Uani 1 1 d . . . . .
H33 H 0.127061 0.443790 0.417681 0.033 Uiso 1 1 calc R U . . .
C1S C 0.35218(19) 0.53751(18) 0.36731(17) 0.0551(11) Uani 1 1 d . . . . .
H1S H 0.309730 0.526953 0.358580 0.066 Uiso 1 1 calc R U . . .
Cl1 Cl 0.38628(6) 0.51876(6) 0.32318(5) 0.0776(4) Uani 1 1 d . . . . .
Cl2 Cl 0.34864(6) 0.49481(5) 0.41513(5) 0.0769(4) Uani 1 1 d . . . . .
Cl3 Cl 0.39546(6) 0.61606(5) 0.37823(5) 0.0735(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C16 1.792(3) . ?
P1 C28 1.794(3) . ?
P1 C22 1.809(3) . ?
P1 C6 1.822(3) . ?
O4 N2 1.250(3) . ?
O5 N2 1.244(4) . ?
N1 C1 1.390(3) . ?
N1 C2 1.398(3) . ?
N1 C8 1.476(3) . ?
N2 O3 1.247(4) . ?
O1 C2 1.215(3) . ?
O2 C1 1.221(3) . ?
C1 C7 1.482(4) 16 ?
C2 C4 1.479(4) . ?
C3 C3 1.406(5) 16 ?
C3 C7 1.408(4) 16 ?
C3 C4 1.409(4) . ?
C4 C5 1.373(4) . ?
C5 C6 1.409(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(4) . ?
C8 C9X 1.516(9) . ?
C8 C9 1.560(5) . ?
C8 H8A 0.983(10) . ?
C8 H8B 0.979(10) . ?
C9 C10 1.527(7) . ?
C9 C12 1.539(6) . ?
C9 H9 1.0000 . ?
C10 C11 1.525(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.507(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.514(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.513(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C9X C10X 1.527(10) . ?
C9X C12X 1.533(10) . ?
C9X H9X 1.0000 . ?
C10X C11X 1.531(12) . ?
C10X H10C 0.9900 . ?
C10X H10D 0.9900 . ?
C11X H11D 0.9800 . ?
C11X H11E 0.9800 . ?
C11X H11F 0.9800 . ?
C12X C13X 1.524(12) . ?
C12X H12C 0.9900 . ?
C12X H12D 0.9900 . ?
C13X C14X 1.528(13) . ?
C13X H13C 0.9900 . ?
C13X H13D 0.9900 . ?
C14X C15X 1.537(14) . ?
C14X H14C 0.9900 . ?
C14X H14D 0.9900 . ?
C15X H15D 0.9800 . ?
C15X H15E 0.9800 . ?
C15X H15F 0.9800 . ?
C16 C17 1.388(4) . ?
C16 C21 1.404(4) . ?
C17 C18 1.384(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.387(5) . ?
C22 C23 1.397(4) . ?
C23 C24 1.380(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.367(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.376(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.387(5) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.391(4) . ?
C28 C33 1.399(4) . ?
C29 C30 1.382(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.387(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.391(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.379(4) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C1S Cl3 1.749(4) . ?
C1S Cl1 1.770(5) . ?
C1S Cl2 1.773(5) . ?
C1S H1S 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
C16 P1 C28 115.34(13) . . ?
C16 P1 C22 106.92(13) . . ?
C28 P1 C22 106.94(13) . . ?
C16 P1 C6 110.50(13) . . ?
C28 P1 C6 111.61(12) . . ?
C22 P1 C6 104.81(12) . . ?
C1 N1 C2 124.2(2) . . ?
C1 N1 C8 118.6(2) . . ?
C2 N1 C8 117.1(2) . . ?
O5 N2 O3 120.5(3) . . ?
O5 N2 O4 118.3(3) . . ?
O3 N2 O4 120.9(3) . . ?
O2 C1 N1 121.1(2) . . ?
O2 C1 C7 120.6(2) . 16 ?
N1 C1 C7 118.3(2) . 16 ?
O1 C2 N1 121.0(2) . . ?
O1 C2 C4 122.4(2) . . ?
N1 C2 C4 116.6(2) . . ?
C3 C3 C7 120.9(3) 16 16 ?
C3 C3 C4 118.5(3) 16 . ?
C7 C3 C4 120.6(2) 16 . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 C2 118.8(2) . . ?
C3 C4 C2 120.8(2) . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 P1 124.5(2) . . ?
C5 C6 P1 116.45(19) . . ?
C6 C7 C3 119.7(2) . 16 ?
C6 C7 C1 121.4(2) . 16 ?
C3 C7 C1 118.9(2) 16 16 ?
N1 C8 C9X 115.2(4) . . ?
N1 C8 C9 112.3(3) . . ?
N1 C8 H8A 107(2) . . ?
C9X C8 H8A 126(2) . . ?
C9 C8 H8A 105(2) . . ?
N1 C8 H8B 106(2) . . ?
C9X C8 H8B 99(2) . . ?
C9 C8 H8B 124(2) . . ?
H8A C8 H8B 99(3) . . ?
C10 C9 C12 112.3(4) . . ?
C10 C9 C8 111.5(4) . . ?
C12 C9 C8 108.6(4) . . ?
C10 C9 H9 108.1 . . ?
C12 C9 H9 108.1 . . ?
C8 C9 H9 108.1 . . ?
C11 C10 C9 113.6(5) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C9 115.8(5) . . ?
C13 C12 H12A 108.3 . . ?
C9 C12 H12A 108.3 . . ?
C13 C12 H12B 108.3 . . ?
C9 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C12 C13 C14 113.7(6) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 113.3(6) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C9X C10X 110.7(7) . . ?
C8 C9X C12X 107.9(7) . . ?
C10X C9X C12X 113.3(7) . . ?
C8 C9X H9X 108.3 . . ?
C10X C9X H9X 108.3 . . ?
C12X C9X H9X 108.3 . . ?
C9X C10X C11X 113.2(9) . . ?
C9X C10X H10C 108.9 . . ?
C11X C10X H10C 108.9 . . ?
C9X C10X H10D 108.9 . . ?
C11X C10X H10D 108.9 . . ?
H10C C10X H10D 107.8 . . ?
C10X C11X H11D 109.5 . . ?
C10X C11X H11E 109.5 . . ?
H11D C11X H11E 109.5 . . ?
C10X C11X H11F 109.5 . . ?
H11D C11X H11F 109.5 . . ?
H11E C11X H11F 109.5 . . ?
C13X C12X C9X 115.9(10) . . ?
C13X C12X H12C 108.3 . . ?
C9X C12X H12C 108.3 . . ?
C13X C12X H12D 108.3 . . ?
C9X C12X H12D 108.3 . . ?
H12C C12X H12D 107.4 . . ?
C12X C13X C14X 113.2(12) . . ?
C12X C13X H13C 108.9 . . ?
C14X C13X H13C 108.9 . . ?
C12X C13X H13D 108.9 . . ?
C14X C13X H13D 108.9 . . ?
H13C C13X H13D 107.7 . . ?
C13X C14X C15X 113.8(14) . . ?
C13X C14X H14C 108.8 . . ?
C15X C14X H14C 108.8 . . ?
C13X C14X H14D 108.8 . . ?
C15X C14X H14D 108.8 . . ?
H14C C14X H14D 107.7 . . ?
C14X C15X H15D 109.5 . . ?
C14X C15X H15E 109.5 . . ?
H15D C15X H15E 109.5 . . ?
C14X C15X H15F 109.5 . . ?
H15D C15X H15F 109.5 . . ?
H15E C15X H15F 109.5 . . ?
C17 C16 C21 120.4(3) . . ?
C17 C16 P1 121.3(2) . . ?
C21 C16 P1 118.2(2) . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 121.0(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 119.6(3) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C16 119.5(3) . . ?
C20 C21 H21 120.2 . . ?
C16 C21 H21 120.2 . . ?
C27 C22 C23 119.0(3) . . ?
C27 C22 P1 120.4(2) . . ?
C23 C22 P1 120.3(2) . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 120.4(4) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 119.9(3) . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?
C29 C28 C33 121.0(3) . . ?
C29 C28 P1 119.9(2) . . ?
C33 C28 P1 119.1(2) . . ?
C30 C29 C28 119.3(3) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C29 C30 C31 120.3(3) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C32 120.1(3) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C33 C32 C31 120.4(3) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C28 118.9(3) . . ?
C32 C33 H33 120.5 . . ?
C28 C33 H33 120.5 . . ?
Cl3 C1S Cl1 109.4(2) . . ?
Cl3 C1S Cl2 110.4(3) . . ?
Cl1 C1S Cl2 109.3(2) . . ?
Cl3 C1S H1S 109.2 . . ?
Cl1 C1S H1S 109.2 . . ?
Cl2 C1S H1S 109.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O2 174.5(2) . . . . ?
C8 N1 C1 O2 -2.0(4) . . . . ?
C2 N1 C1 C7 -3.9(4) . . . 16 ?
C8 N1 C1 C7 179.6(2) . . . 16 ?
C1 N1 C2 O1 178.4(3) . . . . ?
C8 N1 C2 O1 -5.0(4) . . . . ?
C1 N1 C2 C4 -3.5(4) . . . . ?
C8 N1 C2 C4 173.1(2) . . . . ?
C3 C3 C4 C5 -3.8(5) 16 . . . ?
C7 C3 C4 C5 178.0(2) 16 . . . ?
C3 C3 C4 C2 176.4(3) 16 . . . ?
C7 C3 C4 C2 -1.8(4) 16 . . . ?
O1 C2 C4 C5 4.7(4) . . . . ?
N1 C2 C4 C5 -173.4(2) . . . . ?
O1 C2 C4 C3 -175.4(3) . . . . ?
N1 C2 C4 C3 6.5(4) . . . . ?
C3 C4 C5 C6 2.2(4) . . . . ?
C2 C4 C5 C6 -178.0(2) . . . . ?
C4 C5 C6 C7 1.5(4) . . . . ?
C4 C5 C6 P1 -177.5(2) . . . . ?
C16 P1 C6 C7 81.0(3) . . . . ?
C28 P1 C6 C7 -48.8(3) . . . . ?
C22 P1 C6 C7 -164.2(2) . . . . ?
C16 P1 C6 C5 -100.1(2) . . . . ?
C28 P1 C6 C5 130.2(2) . . . . ?
C22 P1 C6 C5 14.8(2) . . . . ?
C5 C6 C7 C3 -3.4(4) . . . 16 ?
P1 C6 C7 C3 175.5(2) . . . 16 ?
C5 C6 C7 C1 174.4(2) . . . 16 ?
P1 C6 C7 C1 -6.6(4) . . . 16 ?
C1 N1 C8 C9X -75.1(5) . . . . ?
C2 N1 C8 C9X 108.2(5) . . . . ?
C1 N1 C8 C9 -105.6(3) . . . . ?
C2 N1 C8 C9 77.6(4) . . . . ?
N1 C8 C9 C10 60.0(5) . . . . ?
N1 C8 C9 C12 -175.8(4) . . . . ?
C12 C9 C10 C11 69.3(7) . . . . ?
C8 C9 C10 C11 -168.5(5) . . . . ?
C10 C9 C12 C13 -169.3(5) . . . . ?
C8 C9 C12 C13 66.9(6) . . . . ?
C9 C12 C13 C14 173.8(6) . . . . ?
C12 C13 C14 C15 -176.5(6) . . . . ?
N1 C8 C9X C10X -57.5(8) . . . . ?
N1 C8 C9X C12X 178.0(6) . . . . ?
C8 C9X C10X C11X 177.7(8) . . . . ?
C12X C9X C10X C11X -61.0(12) . . . . ?
C8 C9X C12X C13X 61.7(12) . . . . ?
C10X C9X C12X C13X -61.2(13) . . . . ?
C9X C12X C13X C14X 177.6(12) . . . . ?
C12X C13X C14X C15X 162.6(15) . . . . ?
C28 P1 C16 C17 112.4(2) . . . . ?
C22 P1 C16 C17 -128.9(2) . . . . ?
C6 P1 C16 C17 -15.4(3) . . . . ?
C28 P1 C16 C21 -71.8(3) . . . . ?
C22 P1 C16 C21 46.9(3) . . . . ?
C6 P1 C16 C21 160.5(2) . . . . ?
C21 C16 C17 C18 0.9(4) . . . . ?
P1 C16 C17 C18 176.7(2) . . . . ?
C16 C17 C18 C19 -1.5(4) . . . . ?
C17 C18 C19 C20 1.2(5) . . . . ?
C18 C19 C20 C21 -0.4(5) . . . . ?
C19 C20 C21 C16 -0.2(5) . . . . ?
C17 C16 C21 C20 -0.1(4) . . . . ?
P1 C16 C21 C20 -176.0(2) . . . . ?
C16 P1 C22 C27 -154.8(2) . . . . ?
C28 P1 C22 C27 -30.8(3) . . . . ?
C6 P1 C22 C27 87.8(3) . . . . ?
C16 P1 C22 C23 31.4(3) . . . . ?
C28 P1 C22 C23 155.4(2) . . . . ?
C6 P1 C22 C23 -86.0(2) . . . . ?
C27 C22 C23 C24 -1.9(4) . . . . ?
P1 C22 C23 C24 172.0(2) . . . . ?
C22 C23 C24 C25 0.9(5) . . . . ?
C23 C24 C25 C26 0.6(6) . . . . ?
C24 C25 C26 C27 -1.1(6) . . . . ?
C25 C26 C27 C22 0.1(6) . . . . ?
C23 C22 C27 C26 1.4(5) . . . . ?
P1 C22 C27 C26 -172.5(3) . . . . ?
C16 P1 C28 C29 22.4(3) . . . . ?
C22 P1 C28 C29 -96.3(2) . . . . ?
C6 P1 C28 C29 149.6(2) . . . . ?
C16 P1 C28 C33 -158.5(2) . . . . ?
C22 P1 C28 C33 82.8(3) . . . . ?
C6 P1 C28 C33 -31.3(3) . . . . ?
C33 C28 C29 C30 0.8(5) . . . . ?
P1 C28 C29 C30 179.8(2) . . . . ?
C28 C29 C30 C31 0.0(5) . . . . ?
C29 C30 C31 C32 -0.9(6) . . . . ?
C30 C31 C32 C33 1.1(6) . . . . ?
C31 C32 C33 C28 -0.3(5) . . . . ?
C29 C28 C33 C32 -0.6(5) . . . . ?
P1 C28 C33 C32 -179.7(3) . . . . ?

_refine_diff_density_max         1.136
_refine_diff_density_min         -0.981
_refine_diff_density_rms         0.090



####################################################################### 
# 
# 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_I440
_database_code_depnum_ccdc_archive 'CCDC 1871421'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H66 I N2 O4 P2'
_chemical_formula_weight         1140.04

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   19.7346(13)
_cell_length_b                   19.9943(12)
_cell_length_c                   14.9829(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.360(2)
_cell_angle_gamma                90
_cell_volume                     5542.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.67

_exptl_crystal_description       Block
_exptl_crystal_colour            Dark_Green
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             2364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    0.687
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7103
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28147
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.900
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6877
_reflns_number_gt                5841
_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_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0807P)²+22.7239P] 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         6877
_refine_ls_number_parameters     413
_refine_ls_number_restraints     213
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1555
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.046
_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
C9 C 0.2187(3) 0.4716(3) 0.2385(3) 0.0358(7) Uani 0.646(3) 1 d D U P A 1
H9 H 0.245590 0.428340 0.247156 0.043 Uiso 0.646(3) 1 calc R U P A 1
C10 C 0.2504(3) 0.5173(3) 0.1817(4) 0.0361(8) Uani 0.646(3) 1 d D U P A 1
H10A H 0.225293 0.560915 0.172958 0.043 Uiso 0.646(3) 1 calc R U P A 1
H10B H 0.301973 0.525279 0.219522 0.043 Uiso 0.646(3) 1 calc R U P A 1
C11 C 0.2454(4) 0.4909(4) 0.0848(4) 0.0365(10) Uani 0.646(3) 1 d D U P A 1
H11A H 0.194574 0.483335 0.046095 0.055 Uiso 0.646(3) 1 calc R U P A 1
H11B H 0.272069 0.448724 0.092458 0.055 Uiso 0.646(3) 1 calc R U P A 1
H11C H 0.266273 0.523700 0.053106 0.055 Uiso 0.646(3) 1 calc R U P A 1
C12 C 0.1381(3) 0.4551(3) 0.1877(4) 0.0385(8) Uani 0.646(3) 1 d D U P A 1
H12A H 0.132705 0.430302 0.128449 0.046 Uiso 0.646(3) 1 calc R U P A 1
H12B H 0.122002 0.425277 0.229159 0.046 Uiso 0.646(3) 1 calc R U P A 1
C13 C 0.0887(3) 0.5162(3) 0.1626(5) 0.0450(8) Uani 0.646(3) 1 d D U P A 1
H13A H 0.100419 0.543641 0.114895 0.054 Uiso 0.646(3) 1 calc R U P A 1
H13B H 0.097313 0.543902 0.220305 0.054 Uiso 0.646(3) 1 calc R U P A 1
C14 C 0.0088(3) 0.4958(4) 0.1225(6) 0.0530(10) Uani 0.646(3) 1 d D U P A 1
H14A H -0.002952 0.467957 0.169842 0.064 Uiso 0.646(3) 1 calc R U P A 1
H14B H -0.000157 0.468743 0.064209 0.064 Uiso 0.646(3) 1 calc R U P A 1
C15 C -0.0400(4) 0.5579(4) 0.0990(6) 0.0610(12) Uani 0.646(3) 1 d D U P A 1
H15A H -0.029524 0.584643 0.050541 0.092 Uiso 0.646(3) 1 calc R U P A 1
H15B H -0.030836 0.584852 0.156738 0.092 Uiso 0.646(3) 1 calc R U P A 1
H15C H -0.090774 0.544001 0.074879 0.092 Uiso 0.646(3) 1 calc R U P A 1
C9X C 0.2191(4) 0.5152(5) 0.2322(5) 0.0357(8) Uani 0.354(3) 1 d D U P A 2
H9X H 0.236587 0.561275 0.225701 0.043 Uiso 0.354(3) 1 calc R U P A 2
C10X C 0.2608(5) 0.4648(5) 0.1947(6) 0.0353(8) Uani 0.354(3) 1 d D U P A 2
H10C H 0.312356 0.466834 0.235856 0.042 Uiso 0.354(3) 1 calc R U P A 2
H10D H 0.243020 0.419446 0.201314 0.042 Uiso 0.354(3) 1 calc R U P A 2
C11X C 0.2562(8) 0.4739(7) 0.0926(6) 0.0368(12) Uani 0.354(3) 1 d D U P A 2
H11D H 0.209201 0.457838 0.049816 0.055 Uiso 0.354(3) 1 calc R U P A 2
H11E H 0.294861 0.448295 0.081491 0.055 Uiso 0.354(3) 1 calc R U P A 2
H11F H 0.261521 0.521384 0.080370 0.055 Uiso 0.354(3) 1 calc R U P A 2
C12X C 0.1365(4) 0.5125(5) 0.1806(7) 0.0401(8) Uani 0.354(3) 1 d D U P A 2
H12C H 0.125600 0.526128 0.113558 0.048 Uiso 0.354(3) 1 calc R U P A 2
H12D H 0.120435 0.465538 0.180327 0.048 Uiso 0.354(3) 1 calc R U P A 2
C13X C 0.0925(4) 0.5563(6) 0.2238(7) 0.0468(10) Uani 0.354(3) 1 d D U P A 2
H13C H 0.114874 0.601215 0.237246 0.056 Uiso 0.354(3) 1 calc R U P A 2
H13D H 0.093944 0.536575 0.285090 0.056 Uiso 0.354(3) 1 calc R U P A 2
C14X C 0.0134(5) 0.5635(7) 0.1580(9) 0.0520(10) Uani 0.354(3) 1 d D U P A 2
H14C H 0.012674 0.589493 0.101470 0.062 Uiso 0.354(3) 1 calc R U P A 2
H14D H -0.012199 0.590368 0.191891 0.062 Uiso 0.354(3) 1 calc R U P A 2
C15X C -0.0335(8) 0.4941(8) 0.1201(11) 0.0592(14) Uani 0.354(3) 1 d . U P A 2
H15D H -0.082462 0.505596 0.077814 0.089 Uiso 0.354(3) 1 calc R U P A 2
H15E H -0.036246 0.468761 0.174724 0.089 Uiso 0.354(3) 1 calc R U P A 2
H15F H -0.009711 0.466897 0.085254 0.089 Uiso 0.354(3) 1 calc R U P A 2
I1 I 0.500000 0.52111(2) 0.750000 0.04270(14) Uani 1 2 d S T P . .
P1 P 0.57447(4) 0.29743(3) 0.56548(5) 0.01641(15) Uani 1 1 d . . . . .
O1 O 0.30794(11) 0.38908(11) 0.41290(16) 0.0262(5) Uani 1 1 d . . . . .
O2 O 0.31301(10) 0.61552(10) 0.39223(14) 0.0195(4) Uani 1 1 d . . . . .
N1 N 0.31163(12) 0.50170(12) 0.39436(17) 0.0167(4) Uani 1 1 d . . . . .
C1 C 0.53807(14) 0.49895(13) 0.51989(18) 0.0142(5) Uani 1 1 d . . . . .
C2 C 0.57442(14) 0.43765(13) 0.54567(18) 0.0151(5) Uani 1 1 d . . . . .
C3 C 0.53386(14) 0.37773(13) 0.53227(18) 0.0160(5) Uani 1 1 d . . . . .
C4 C 0.45888(14) 0.38022(14) 0.49413(19) 0.0173(5) Uani 1 1 d . . . . .
H4 H 0.431864 0.339951 0.486123 0.021 Uiso 1 1 calc R U . . .
C5 C 0.42276(14) 0.44076(13) 0.46750(19) 0.0160(5) Uani 1 1 d . . . . .
C6 C 0.34451(14) 0.44014(14) 0.42422(19) 0.0182(5) Uani 1 1 d . . . . .
C7 C 0.34743(14) 0.56275(13) 0.41258(18) 0.0160(5) Uani 1 1 d . . . . .
C8 C 0.23379(15) 0.50083(16) 0.3385(2) 0.0217(6) Uani 1 1 d D . . . .
H8A H 0.213(2) 0.4709(17) 0.369(3) 0.033 Uiso 1 1 d D U . . .
H8B H 0.215(2) 0.5433(12) 0.339(3) 0.033 Uiso 1 1 d D U . . .
C16 C 0.50155(15) 0.23794(13) 0.5442(2) 0.0215(6) Uani 1 1 d . . . . .
C17 C 0.48391(19) 0.21200(16) 0.6192(3) 0.0311(7) Uani 1 1 d . . . . .
H17 H 0.512477 0.222960 0.682889 0.037 Uiso 1 1 calc R U . . .
C18 C 0.4245(2) 0.16998(19) 0.6012(3) 0.0419(9) Uani 1 1 d . . . . .
H18 H 0.412895 0.151774 0.652718 0.050 Uiso 1 1 calc R U . . .
C19 C 0.3823(2) 0.15470(19) 0.5087(3) 0.0438(10) Uani 1 1 d . . . . .
H19 H 0.341104 0.126813 0.496674 0.053 Uiso 1 1 calc R U . . .
C20 C 0.3996(2) 0.17962(19) 0.4340(3) 0.0427(9) Uani 1 1 d . . . . .
H20 H 0.370519 0.168589 0.370578 0.051 Uiso 1 1 calc R U . . .
C21 C 0.45942(19) 0.22085(17) 0.4505(3) 0.0327(7) Uani 1 1 d . . . . .
H21 H 0.471687 0.237354 0.398606 0.039 Uiso 1 1 calc R U . . .
C22 C 0.62304(15) 0.29567(13) 0.69199(19) 0.0176(5) Uani 1 1 d . . . . .
C23 C 0.67647(16) 0.24911(15) 0.7361(2) 0.0223(6) Uani 1 1 d . . . . .
H23 H 0.689229 0.215966 0.699335 0.027 Uiso 1 1 calc R U . . .
C24 C 0.71126(17) 0.25121(17) 0.8344(2) 0.0281(7) Uani 1 1 d . . . . .
H24 H 0.748101 0.219667 0.864712 0.034 Uiso 1 1 calc R U . . .
C25 C 0.69222(17) 0.29930(17) 0.8884(2) 0.0273(6) Uani 1 1 d . . . . .
H25 H 0.716191 0.300601 0.955420 0.033 Uiso 1 1 calc R U . . .
C26 C 0.63864(16) 0.34517(16) 0.8450(2) 0.0242(6) Uani 1 1 d . . . . .
H26 H 0.625895 0.378001 0.882188 0.029 Uiso 1 1 calc R U . . .
C27 C 0.60311(16) 0.34346(14) 0.7466(2) 0.0208(5) Uani 1 1 d . . . . .
H27 H 0.565637 0.374532 0.716768 0.025 Uiso 1 1 calc R U . . .
C28 C 0.62023(16) 0.27100(15) 0.4870(2) 0.0223(6) Uani 1 1 d . . . . .
C29 C 0.65172(17) 0.20762(17) 0.4975(2) 0.0290(7) Uani 1 1 d . . . . .
H29 H 0.651810 0.179647 0.548772 0.035 Uiso 1 1 calc R U . . .
C30 C 0.68272(18) 0.18570(19) 0.4332(3) 0.0358(8) Uani 1 1 d . . . . .
H30 H 0.705593 0.143200 0.441254 0.043 Uiso 1 1 calc R U . . .
C31 C 0.68038(19) 0.2258(2) 0.3571(3) 0.0384(8) Uani 1 1 d . . . . .
H31 H 0.701699 0.210431 0.312891 0.046 Uiso 1 1 calc R U . . .
C32 C 0.6477(2) 0.2874(2) 0.3442(3) 0.0383(8) Uani 1 1 d . . . . .
H32 H 0.645548 0.313989 0.290716 0.046 Uiso 1 1 calc R U . . .
C33 C 0.61763(18) 0.31102(17) 0.4103(2) 0.0289(7) Uani 1 1 d . . . . .
H33 H 0.595711 0.353950 0.402616 0.035 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C9 C10 1.523(6) . ?
C9 C8 1.537(5) . ?
C9 C12 1.542(6) . ?
C9 H9 1.0000 . ?
C10 C11 1.515(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.526(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.534(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.536(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C9X C10X 1.526(7) . ?
C9X C12X 1.543(7) . ?
C9X C8 1.543(7) . ?
C9X H9X 1.0000 . ?
C10X C11X 1.511(7) . ?
C10X H10C 0.9900 . ?
C10X H10D 0.9900 . ?
C11X H11D 0.9800 . ?
C11X H11E 0.9800 . ?
C11X H11F 0.9800 . ?
C12X C13X 1.527(8) . ?
C12X H12C 0.9900 . ?
C12X H12D 0.9900 . ?
C13X C14X 1.536(8) . ?
C13X H13C 0.9900 . ?
C13X H13D 0.9900 . ?
C14X C15X 1.65(2) . ?
C14X H14C 0.9900 . ?
C14X H14D 0.9900 . ?
C15X H15D 0.9800 . ?
C15X H15E 0.9800 . ?
C15X H15F 0.9800 . ?
P1 C3 1.786(3) . ?
P1 C28 1.794(3) . ?
P1 C22 1.802(3) . ?
P1 C16 1.808(3) . ?
O1 C6 1.227(4) . ?
O2 C7 1.234(3) . ?
N1 C7 1.389(4) . ?
N1 C6 1.391(3) . ?
N1 C8 1.472(3) . ?
C1 C2 1.405(4) . ?
C1 C5 1.409(4) 5_666 ?
C1 C1 1.411(5) 5_666 ?
C2 C3 1.416(4) . ?
C2 C7 1.449(4) 5_666 ?
C3 C4 1.389(4) . ?
C4 C5 1.391(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.452(4) . ?
C8 H8A 0.939(19) . ?
C8 H8B 0.927(19) . ?
C16 C17 1.387(5) . ?
C16 C21 1.403(4) . ?
C17 C18 1.391(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.373(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.389(4) . ?
C22 C27 1.400(4) . ?
C23 C24 1.393(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.396(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.386(5) . ?
C28 C29 1.396(4) . ?
C29 C30 1.380(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.382(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.373(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.402(5) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C9 C8 109.8(4) . . ?
C10 C9 C12 114.0(4) . . ?
C8 C9 C12 112.3(4) . . ?
C10 C9 H9 106.8 . . ?
C8 C9 H9 106.8 . . ?
C12 C9 H9 106.8 . . ?
C11 C10 C9 115.1(5) . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C9 114.3(4) . . ?
C13 C12 H12A 108.7 . . ?
C9 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C9 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 111.4(5) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.6(6) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10X C9X C12X 113.8(6) . . ?
C10X C9X C8 109.0(6) . . ?
C12X C9X C8 107.2(6) . . ?
C10X C9X H9X 108.9 . . ?
C12X C9X H9X 108.9 . . ?
C8 C9X H9X 108.9 . . ?
C11X C10X C9X 116.3(7) . . ?
C11X C10X H10C 108.2 . . ?
C9X C10X H10C 108.2 . . ?
C11X C10X H10D 108.2 . . ?
C9X C10X H10D 108.2 . . ?
H10C C10X H10D 107.4 . . ?
C10X C11X H11D 109.5 . . ?
C10X C11X H11E 109.5 . . ?
H11D C11X H11E 109.5 . . ?
C10X C11X H11F 109.5 . . ?
H11D C11X H11F 109.5 . . ?
H11E C11X H11F 109.5 . . ?
C13X C12X C9X 115.1(6) . . ?
C13X C12X H12C 108.5 . . ?
C9X C12X H12C 108.5 . . ?
C13X C12X H12D 108.5 . . ?
C9X C12X H12D 108.5 . . ?
H12C C12X H12D 107.5 . . ?
C12X C13X C14X 112.5(7) . . ?
C12X C13X H13C 109.1 . . ?
C14X C13X H13C 109.1 . . ?
C12X C13X H13D 109.1 . . ?
C14X C13X H13D 109.1 . . ?
H13C C13X H13D 107.8 . . ?
C13X C14X C15X 117.7(10) . . ?
C13X C14X H14C 107.9 . . ?
C15X C14X H14C 107.9 . . ?
C13X C14X H14D 107.9 . . ?
C15X C14X H14D 107.9 . . ?
H14C C14X H14D 107.2 . . ?
C14X C15X H15D 109.5 . . ?
C14X C15X H15E 109.5 . . ?
H15D C15X H15E 109.5 . . ?
C14X C15X H15F 109.5 . . ?
H15D C15X H15F 109.5 . . ?
H15E C15X H15F 109.5 . . ?
C3 P1 C28 111.19(13) . . ?
C3 P1 C22 109.48(12) . . ?
C28 P1 C22 118.62(13) . . ?
C3 P1 C16 106.85(13) . . ?
C28 P1 C16 104.00(14) . . ?
C22 P1 C16 105.79(13) . . ?
C7 N1 C6 124.5(2) . . ?
C7 N1 C8 118.8(2) . . ?
C6 N1 C8 116.8(2) . . ?
C2 C1 C5 120.4(2) . 5_666 ?
C2 C1 C1 120.6(3) . 5_666 ?
C5 C1 C1 119.0(3) 5_666 5_666 ?
C1 C2 C3 119.3(2) . . ?
C1 C2 C7 119.3(2) . 5_666 ?
C3 C2 C7 121.4(2) . 5_666 ?
C4 C3 C2 119.8(2) . . ?
C4 C3 P1 117.2(2) . . ?
C2 C3 P1 122.99(19) . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C1 120.2(2) . 5_666 ?
C4 C5 C6 118.7(2) . . ?
C1 C5 C6 121.1(2) 5_666 . ?
O1 C6 N1 120.4(2) . . ?
O1 C6 C5 123.5(2) . . ?
N1 C6 C5 116.1(2) . . ?
O2 C7 N1 120.3(2) . . ?
O2 C7 C2 121.5(2) . 5_666 ?
N1 C7 C2 118.2(2) . 5_666 ?
N1 C8 C9 111.7(3) . . ?
N1 C8 C9X 111.7(3) . . ?
N1 C8 H8A 106(2) . . ?
C9 C8 H8A 106(3) . . ?
C9X C8 H8A 132(3) . . ?
N1 C8 H8B 109(2) . . ?
C9 C8 H8B 115(3) . . ?
C9X C8 H8B 85(3) . . ?
H8A C8 H8B 109(4) . . ?
C17 C16 C21 119.4(3) . . ?
C17 C16 P1 120.8(2) . . ?
C21 C16 P1 119.7(3) . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.5(4) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 119.6(4) . . ?
C20 C21 H21 120.2 . . ?
C16 C21 H21 120.2 . . ?
C23 C22 C27 120.0(3) . . ?
C23 C22 P1 123.5(2) . . ?
C27 C22 P1 116.5(2) . . ?
C22 C23 C24 119.7(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 120.2(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 120.3(3) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 120.2(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C22 119.6(3) . . ?
C26 C27 H27 120.2 . . ?
C22 C27 H27 120.2 . . ?
C33 C28 C29 120.3(3) . . ?
C33 C28 P1 119.4(2) . . ?
C29 C28 P1 120.0(2) . . ?
C30 C29 C28 119.8(3) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 119.8(3) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C32 C31 C30 121.0(3) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C31 C32 C33 119.8(4) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C28 C33 C32 119.2(3) . . ?
C28 C33 H33 120.4 . . ?
C32 C33 H33 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C9 C10 C11 174.6(5) . . . . ?
C12 C9 C10 C11 -58.4(7) . . . . ?
C10 C9 C12 C13 -58.7(7) . . . . ?
C8 C9 C12 C13 67.0(6) . . . . ?
C9 C12 C13 C14 -173.7(6) . . . . ?
C12 C13 C14 C15 179.2(6) . . . . ?
C12X C9X C10X C11X 63.8(13) . . . . ?
C8 C9X C10X C11X -176.6(9) . . . . ?
C10X C9X C12X C13X 173.1(9) . . . . ?
C8 C9X C12X C13X 52.5(11) . . . . ?
C9X C12X C13X C14X 167.4(10) . . . . ?
C12X C13X C14X C15X 54.8(16) . . . . ?
C5 C1 C2 C3 -180.0(2) 5_666 . . . ?
C1 C1 C2 C3 -0.6(4) 5_666 . . . ?
C5 C1 C2 C7 1.4(4) 5_666 . . 5_666 ?
C1 C1 C2 C7 -179.2(3) 5_666 . . 5_666 ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C7 C2 C3 C4 178.4(2) 5_666 . . . ?
C1 C2 C3 P1 -178.30(19) . . . . ?
C7 C2 C3 P1 0.3(4) 5_666 . . . ?
C28 P1 C3 C4 109.9(2) . . . . ?
C22 P1 C3 C4 -117.1(2) . . . . ?
C16 P1 C3 C4 -2.9(2) . . . . ?
C28 P1 C3 C2 -71.9(3) . . . . ?
C22 P1 C3 C2 61.1(3) . . . . ?
C16 P1 C3 C2 175.3(2) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
P1 C3 C4 C5 179.2(2) . . . . ?
C3 C4 C5 C1 -0.9(4) . . . 5_666 ?
C3 C4 C5 C6 177.4(2) . . . . ?
C7 N1 C6 O1 173.2(3) . . . . ?
C8 N1 C6 O1 -7.8(4) . . . . ?
C7 N1 C6 C5 -7.3(4) . . . . ?
C8 N1 C6 C5 171.7(2) . . . . ?
C4 C5 C6 O1 2.8(4) . . . . ?
C1 C5 C6 O1 -179.0(3) 5_666 . . . ?
C4 C5 C6 N1 -176.6(2) . . . . ?
C1 C5 C6 N1 1.6(4) 5_666 . . . ?
C6 N1 C7 O2 -172.4(3) . . . . ?
C8 N1 C7 O2 8.6(4) . . . . ?
C6 N1 C7 C2 8.5(4) . . . 5_666 ?
C8 N1 C7 C2 -170.4(2) . . . 5_666 ?
C7 N1 C8 C9 108.6(3) . . . . ?
C6 N1 C8 C9 -70.4(4) . . . . ?
C7 N1 C8 C9X 73.0(5) . . . . ?
C6 N1 C8 C9X -106.1(4) . . . . ?
C10 C9 C8 N1 -65.3(4) . . . . ?
C12 C9 C8 N1 166.7(3) . . . . ?
C10X C9X C8 N1 55.9(7) . . . . ?
C12X C9X C8 N1 179.5(5) . . . . ?
C3 P1 C16 C17 -104.0(3) . . . . ?
C28 P1 C16 C17 138.3(3) . . . . ?
C22 P1 C16 C17 12.6(3) . . . . ?
C3 P1 C16 C21 72.1(3) . . . . ?
C28 P1 C16 C21 -45.6(3) . . . . ?
C22 P1 C16 C21 -171.3(2) . . . . ?
C21 C16 C17 C18 -0.7(5) . . . . ?
P1 C16 C17 C18 175.4(3) . . . . ?
C16 C17 C18 C19 -0.9(5) . . . . ?
C17 C18 C19 C20 1.4(6) . . . . ?
C18 C19 C20 C21 -0.5(6) . . . . ?
C19 C20 C21 C16 -1.1(5) . . . . ?
C17 C16 C21 C20 1.6(5) . . . . ?
P1 C16 C21 C20 -174.5(3) . . . . ?
C3 P1 C22 C23 -161.0(2) . . . . ?
C28 P1 C22 C23 -32.0(3) . . . . ?
C16 P1 C22 C23 84.2(3) . . . . ?
C3 P1 C22 C27 20.6(3) . . . . ?
C28 P1 C22 C27 149.7(2) . . . . ?
C16 P1 C22 C27 -94.2(2) . . . . ?
C27 C22 C23 C24 -1.5(4) . . . . ?
P1 C22 C23 C24 -179.8(2) . . . . ?
C22 C23 C24 C25 0.5(5) . . . . ?
C23 C24 C25 C26 0.2(5) . . . . ?
C24 C25 C26 C27 0.1(5) . . . . ?
C25 C26 C27 C22 -1.1(4) . . . . ?
C23 C22 C27 C26 1.8(4) . . . . ?
P1 C22 C27 C26 -179.8(2) . . . . ?
C3 P1 C28 C33 -2.6(3) . . . . ?
C22 P1 C28 C33 -130.9(2) . . . . ?
C16 P1 C28 C33 112.0(3) . . . . ?
C3 P1 C28 C29 -176.1(2) . . . . ?
C22 P1 C28 C29 55.7(3) . . . . ?
C16 P1 C28 C29 -61.4(3) . . . . ?
C33 C28 C29 C30 2.3(5) . . . . ?
P1 C28 C29 C30 175.7(3) . . . . ?
C28 C29 C30 C31 -2.0(5) . . . . ?
C29 C30 C31 C32 0.1(6) . . . . ?
C30 C31 C32 C33 1.5(6) . . . . ?
C29 C28 C33 C32 -0.7(5) . . . . ?
P1 C28 C33 C32 -174.2(3) . . . . ?
C31 C32 C33 C28 -1.1(5) . . . . ?

_refine_diff_density_max         2.710
_refine_diff_density_min         -1.072
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_h398
_database_code_depnum_ccdc_archive 'CCDC 1871420'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H34 Br Cl3 N O2 P'
_chemical_formula_sum            'C34 H34 Br Cl3 N O2 P'
_chemical_formula_weight         705.85

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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   10.9670(6)
_cell_length_b                   15.8648(10)
_cell_length_c                   20.3172(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.084(3)
_cell_angle_gamma                90
_cell_volume                     3413.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3273
_cell_measurement_theta_min      3.583
_cell_measurement_theta_max      75.436

_exptl_crystal_description       'prism frag'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             1448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    4.484
_shelx_estimated_absorpt_T_min   0.486
_shelx_estimated_absorpt_T_max   0.573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_T_max  0.573
_exptl_absorpt_process_details   Sadabs
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24969
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.583
_diffrn_reflns_theta_max         75.436
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             6662
_reflns_number_gt                5263
_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 v2016.9.0'
_computing_cell_refinement       
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2016.9.0'
_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)+(0.0771P)²+13.2757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6662
_refine_ls_number_parameters     457
_refine_ls_number_restraints     220
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1801
_refine_ls_wR_factor_gt          0.1632
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.035
_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
Br1 Br 0.22821(5) 0.35501(4) 0.48590(3) 0.04283(18) Uani 1 1 d . . . . .
P1 P 0.47974(10) 0.62564(6) 0.68629(5) 0.0241(2) Uani 1 1 d . . . . .
N1 N 0.4468(3) 0.7182(2) 0.47072(16) 0.0232(7) Uani 1 1 d . . . . .
O1 O 0.4868(3) 0.73772(17) 0.58546(14) 0.0291(6) Uani 1 1 d . . . . .
O2 O 0.4283(3) 0.69664(17) 0.35792(14) 0.0297(6) Uani 1 1 d . . . . .
C1 C 0.4752(4) 0.6890(2) 0.5377(2) 0.0239(8) Uani 1 1 d . . . . .
C2 C 0.4875(4) 0.5972(2) 0.54941(19) 0.0231(8) Uani 1 1 d . . . . .
C3 C 0.4991(4) 0.5634(2) 0.61406(19) 0.0224(8) Uani 1 1 d . . . . .
C4 C 0.5180(4) 0.4757(2) 0.62400(19) 0.0241(8) Uani 1 1 d . . . . .
H4 H 0.5254 0.4524 0.6680 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5259(4) 0.4236(2) 0.5715(2) 0.0237(8) Uani 1 1 d . . . . .
C6 C 0.5091(4) 0.4564(2) 0.50514(19) 0.0225(8) Uani 1 1 d . . . . .
C7 C 0.4491(4) 0.6674(3) 0.41508(19) 0.0246(8) Uani 1 1 d . . . . .
C8A C 0.4330(8) 0.8094(6) 0.4616(9) 0.0303(11) Uani 0.668(5) 1 d D U P A 1
H8A1 H 0.4366 0.8240 0.4147 0.036 Uiso 0.668(5) 1 calc R U P A 1
H8A2 H 0.5049 0.8376 0.4937 0.036 Uiso 0.668(5) 1 calc R U P A 1
C9A C 0.3102(5) 0.8430(4) 0.4732(3) 0.0338(10) Uani 0.668(5) 1 d D U P A 1
H9A H 0.3057 0.8247 0.5196 0.041 Uiso 0.668(5) 1 calc R U P A 1
C12A C 0.3156(7) 0.9404(4) 0.4726(4) 0.0389(12) Uani 0.668(5) 1 d D U P A 1
H12A H 0.3939 0.9588 0.5060 0.047 Uiso 0.668(5) 1 calc R U P A 1
H12B H 0.3210 0.9591 0.4270 0.047 Uiso 0.668(5) 1 calc R U P A 1
C13A C 0.2048(9) 0.9840(5) 0.4891(4) 0.0481(13) Uani 0.668(5) 1 d D U P A 1
H13A H 0.1866 0.9563 0.5291 0.058 Uiso 0.668(5) 1 calc R U P A 1
H13B H 0.1295 0.9771 0.4501 0.058 Uiso 0.668(5) 1 calc R U P A 1
C14A C 0.2282(9) 1.0820(5) 0.5048(5) 0.0544(14) Uani 0.668(5) 1 d D U P A 1
H14A H 0.3066 1.0895 0.5417 0.065 Uiso 0.668(5) 1 calc R U P A 1
H14B H 0.2393 1.1110 0.4636 0.065 Uiso 0.668(5) 1 calc R U P A 1
C15A C 0.1192(9) 1.1210(5) 0.5260(5) 0.0609(17) Uani 0.668(5) 1 d D U P A 1
H15A H 0.0404 1.1088 0.4915 0.091 Uiso 0.668(5) 1 calc R U P A 1
H15B H 0.1313 1.1821 0.5303 0.091 Uiso 0.668(5) 1 calc R U P A 1
H15C H 0.1149 1.0974 0.5699 0.091 Uiso 0.668(5) 1 calc R U P A 1
C10A C 0.1951(7) 0.8078(5) 0.4216(3) 0.0396(12) Uani 0.668(5) 1 d D U P A 1
H10A H 0.1189 0.8238 0.4361 0.048 Uiso 0.668(5) 1 calc R U P A 1
H10B H 0.2007 0.7455 0.4229 0.048 Uiso 0.668(5) 1 calc R U P A 1
C11A C 0.1774(8) 0.8362(5) 0.3481(3) 0.0429(13) Uani 0.668(5) 1 d D U P A 1
H11A H 0.1656 0.8975 0.3453 0.064 Uiso 0.668(5) 1 calc R U P A 1
H11B H 0.1029 0.8085 0.3190 0.064 Uiso 0.668(5) 1 calc R U P A 1
H11C H 0.2522 0.8210 0.3329 0.064 Uiso 0.668(5) 1 calc R U P A 1
C8B C 0.4168(14) 0.8112(11) 0.4578(19) 0.0327(17) Uani 0.332(5) 1 d D U P A 2
H8B1 H 0.4658 0.8337 0.4271 0.039 Uiso 0.332(5) 1 calc R U P A 2
H8B2 H 0.4427 0.8423 0.5015 0.039 Uiso 0.332(5) 1 calc R U P A 2
C9B C 0.2767(12) 0.8254(6) 0.4258(6) 0.0375(13) Uani 0.332(5) 1 d D U P A 2
H9B H 0.2546 0.7974 0.3801 0.045 Uiso 0.332(5) 1 calc R U P A 2
C12B C 0.2547(15) 0.9213(6) 0.4142(5) 0.0408(13) Uani 0.332(5) 1 d D U P A 2
H12C H 0.3156 0.9428 0.3898 0.049 Uiso 0.332(5) 1 calc R U P A 2
H12D H 0.1688 0.9300 0.3843 0.049 Uiso 0.332(5) 1 calc R U P A 2
C13B C 0.2681(18) 0.9726(7) 0.4781(6) 0.0470(15) Uani 0.332(5) 1 d D U P A 2
H13C H 0.3588 0.9759 0.5026 0.056 Uiso 0.332(5) 1 calc R U P A 2
H13D H 0.2241 0.9430 0.5082 0.056 Uiso 0.332(5) 1 calc R U P A 2
C14B C 0.2133(19) 1.0659(8) 0.4650(7) 0.0536(17) Uani 0.332(5) 1 d D U P A 2
H14C H 0.2564 1.0962 0.4348 0.064 Uiso 0.332(5) 1 calc R U P A 2
H14D H 0.1220 1.0635 0.4418 0.064 Uiso 0.332(5) 1 calc R U P A 2
C15B C 0.2327(19) 1.1131(8) 0.5313(8) 0.0539(19) Uani 0.332(5) 1 d D U P A 2
H15D H 0.1766 1.0900 0.5573 0.081 Uiso 0.332(5) 1 calc R U P A 2
H15E H 0.2133 1.1729 0.5219 0.081 Uiso 0.332(5) 1 calc R U P A 2
H15F H 0.3207 1.1071 0.5578 0.081 Uiso 0.332(5) 1 calc R U P A 2
C10B C 0.1944(11) 0.7868(9) 0.4677(8) 0.044(4) Uani 0.332(5) 1 d D . P A 2
H10C H 0.2094 0.7252 0.4708 0.053 Uiso 0.332(5) 1 calc R U P A 2
H10D H 0.2208 0.8099 0.5145 0.053 Uiso 0.332(5) 1 calc R U P A 2
C11B C 0.0536(12) 0.8024(12) 0.4392(10) 0.061(5) Uani 0.332(5) 1 d D . P A 2
H11D H 0.0339 0.8607 0.4486 0.092 Uiso 0.332(5) 1 calc R U P A 2
H11E H 0.0060 0.7638 0.4608 0.092 Uiso 0.332(5) 1 calc R U P A 2
H11F H 0.0303 0.7928 0.3898 0.092 Uiso 0.332(5) 1 calc R U P A 2
C16 C 0.3306(4) 0.6801(3) 0.6617(2) 0.0294(9) Uani 1 1 d . . . . .
C17 C 0.2335(4) 0.6464(3) 0.6101(2) 0.0373(10) Uani 1 1 d . . . . .
H17 H 0.2466 0.5961 0.5875 0.045 Uiso 1 1 calc R U . . .
C18 C 0.1181(5) 0.6865(4) 0.5921(3) 0.0524(14) Uani 1 1 d . . . . .
H18 H 0.0521 0.6641 0.5564 0.063 Uiso 1 1 calc R U . . .
C19 C 0.0976(5) 0.7588(4) 0.6254(3) 0.0539(14) Uani 1 1 d . . . . .
H19 H 0.0177 0.7860 0.6127 0.065 Uiso 1 1 calc R U . . .
C20 C 0.1929(6) 0.7914(4) 0.6769(3) 0.0509(14) Uani 1 1 d . . . . .
H20 H 0.1778 0.8407 0.7000 0.061 Uiso 1 1 calc R U . . .
C21 C 0.3115(5) 0.7531(3) 0.6957(2) 0.0351(10) Uani 1 1 d . . . . .
H21 H 0.3776 0.7763 0.7310 0.042 Uiso 1 1 calc R U . . .
C22 C 0.6178(4) 0.6868(3) 0.7242(2) 0.0294(9) Uani 1 1 d . . . . .
C23 C 0.6279(4) 0.7224(3) 0.7886(2) 0.0338(10) Uani 1 1 d . . . . .
H23 H 0.5609 0.7168 0.8100 0.041 Uiso 1 1 calc R U . . .
C24 C 0.7366(5) 0.7657(3) 0.8208(3) 0.0442(12) Uani 1 1 d . . . . .
H24 H 0.7439 0.7908 0.8641 0.053 Uiso 1 1 calc R U . . .
C25 C 0.8346(5) 0.7725(4) 0.7899(3) 0.0506(13) Uani 1 1 d . . . . .
H25 H 0.9092 0.8020 0.8123 0.061 Uiso 1 1 calc R U . . .
C26 C 0.8252(5) 0.7368(3) 0.7267(3) 0.0429(11) Uani 1 1 d . . . . .
H26 H 0.8934 0.7417 0.7061 0.052 Uiso 1 1 calc R U . . .
C27 C 0.7158(4) 0.6934(3) 0.6928(2) 0.0337(10) Uani 1 1 d . . . . .
H27 H 0.7087 0.6690 0.6493 0.040 Uiso 1 1 calc R U . . .
C28 C 0.4657(5) 0.5492(3) 0.7498(2) 0.0310(10) Uani 1 1 d . . . . .
C29 C 0.3467(5) 0.5169(3) 0.7485(2) 0.0399(11) Uani 1 1 d . . . . .
H29 H 0.2732 0.5395 0.7180 0.048 Uiso 1 1 calc R U . . .
C30 C 0.3368(7) 0.4515(3) 0.7924(3) 0.0559(15) Uani 1 1 d . . . . .
H30 H 0.2559 0.4297 0.7920 0.067 Uiso 1 1 calc R U . . .
C31 C 0.4412(7) 0.4184(3) 0.8356(3) 0.0570(16) Uani 1 1 d . . . . .
H31 H 0.4329 0.3732 0.8648 0.068 Uiso 1 1 calc R U . . .
C32 C 0.5596(7) 0.4498(3) 0.8377(3) 0.0558(17) Uani 1 1 d . . . . .
H32 H 0.6323 0.4266 0.8685 0.067 Uiso 1 1 calc R U . . .
C33 C 0.5723(5) 0.5162(3) 0.7943(2) 0.0414(11) Uani 1 1 d . . . . .
H33 H 0.6534 0.5382 0.7955 0.050 Uiso 1 1 calc R U . . .
Cl1S Cl 0.16206(14) 0.59102(10) 0.34745(9) 0.0644(4) Uani 1 1 d . . . . .
Cl2S Cl -0.00771(15) 0.45532(11) 0.29272(8) 0.0634(4) Uani 1 1 d . . . . .
Cl3S Cl -0.04230(13) 0.55080(8) 0.40954(7) 0.0511(3) Uani 1 1 d . . . . .
C1S C 0.0670(6) 0.5091(4) 0.3680(3) 0.0524(13) Uani 1 1 d . . . . .
H1S H 0.1233 0.4686 0.3996 0.063 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C22 1.794(5) . ?
P1 C16 1.801(4) . ?
P1 C28 1.806(4) . ?
P1 C3 1.826(4) . ?
N1 C1 1.393(5) . ?
N1 C7 1.394(5) . ?
N1 C8A 1.462(9) . ?
N1 C8B 1.519(16) . ?
O1 C1 1.222(5) . ?
O2 C7 1.216(5) . ?
C1 C2 1.475(5) . ?
C2 C3 1.393(5) . ?
C2 C6 1.405(5) 3_666 ?
C3 C4 1.414(5) . ?
C4 C5 1.370(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(5) . ?
C5 C7 1.481(5) 3_666 ?
C6 C2 1.405(5) 3_666 ?
C6 C6 1.407(8) 3_666 ?
C7 C5 1.481(5) 3_666 ?
C8A C9A 1.522(5) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A C10A 1.522(5) . ?
C9A C12A 1.546(8) . ?
C9A H9A 1.0000 . ?
C12A C13A 1.510(9) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A C14A 1.595(11) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C14A C15A 1.505(11) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C10A C11A 1.522(5) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C8B C9B 1.522(6) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B C10B 1.521(6) . ?
C9B C12B 1.547(9) . ?
C9B H9B 1.0000 . ?
C12B C13B 1.507(10) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B C14B 1.594(11) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B C15B 1.507(11) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C10B C11B 1.521(6) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C16 C17 1.392(7) . ?
C16 C21 1.393(6) . ?
C17 C18 1.378(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.373(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.396(7) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.389(6) . ?
C22 C23 1.404(6) . ?
C23 C24 1.383(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.399(7) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.381(7) . ?
C28 C29 1.395(7) . ?
C29 C30 1.391(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.354(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.381(10) . ?
C31 H31 0.9500 . ?
C32 C33 1.404(8) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
Cl1S C1S 1.783(6) . ?
Cl2S C1S 1.757(6) . ?
Cl3S C1S 1.764(6) . ?
C1S H1S 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
C22 P1 C16 117.6(2) . . ?
C22 P1 C28 106.0(2) . . ?
C16 P1 C28 106.3(2) . . ?
C22 P1 C3 112.05(19) . . ?
C16 P1 C3 108.84(19) . . ?
C28 P1 C3 105.08(18) . . ?
C1 N1 C7 123.5(3) . . ?
C1 N1 C8A 116.3(7) . . ?
C7 N1 C8A 119.5(7) . . ?
C1 N1 C8B 118.3(14) . . ?
C7 N1 C8B 118.1(14) . . ?
O1 C1 N1 121.0(3) . . ?
O1 C1 C2 120.6(3) . . ?
N1 C1 C2 118.3(3) . . ?
C3 C2 C6 119.7(3) . 3_666 ?
C3 C2 C1 120.9(3) . . ?
C6 C2 C1 119.3(3) 3_666 . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 P1 123.3(3) . . ?
C4 C3 P1 117.4(3) . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 C7 119.4(3) . 3_666 ?
C6 C5 C7 120.4(3) . 3_666 ?
C2 C6 C6 120.7(4) 3_666 3_666 ?
C2 C6 C5 120.5(3) 3_666 . ?
C6 C6 C5 118.8(4) 3_666 . ?
O2 C7 N1 121.0(4) . . ?
O2 C7 C5 121.9(4) . 3_666 ?
N1 C7 C5 117.1(3) . 3_666 ?
N1 C8A C9A 113.2(7) . . ?
N1 C8A H8A1 108.9 . . ?
C9A C8A H8A1 108.9 . . ?
N1 C8A H8A2 108.9 . . ?
C9A C8A H8A2 108.9 . . ?
H8A1 C8A H8A2 107.8 . . ?
C10A C9A C8A 112.0(8) . . ?
C10A C9A C12A 112.9(5) . . ?
C8A C9A C12A 108.1(5) . . ?
C10A C9A H9A 107.9 . . ?
C8A C9A H9A 107.9 . . ?
C12A C9A H9A 107.9 . . ?
C13A C12A C9A 115.0(5) . . ?
C13A C12A H12A 108.5 . . ?
C9A C12A H12A 108.5 . . ?
C13A C12A H12B 108.5 . . ?
C9A C12A H12B 108.5 . . ?
H12A C12A H12B 107.5 . . ?
C12A C13A C14A 113.2(7) . . ?
C12A C13A H13A 108.9 . . ?
C14A C13A H13A 108.9 . . ?
C12A C13A H13B 108.9 . . ?
C14A C13A H13B 108.9 . . ?
H13A C13A H13B 107.7 . . ?
C15A C14A C13A 111.1(7) . . ?
C15A C14A H14A 109.4 . . ?
C13A C14A H14A 109.4 . . ?
C15A C14A H14B 109.4 . . ?
C13A C14A H14B 109.4 . . ?
H14A C14A H14B 108.0 . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C9A C10A C11A 116.0(6) . . ?
C9A C10A H10A 108.3 . . ?
C11A C10A H10A 108.3 . . ?
C9A C10A H10B 108.3 . . ?
C11A C10A H10B 108.3 . . ?
H10A C10A H10B 107.4 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
N1 C8B C9B 111.6(12) . . ?
N1 C8B H8B1 109.3 . . ?
C9B C8B H8B1 109.3 . . ?
N1 C8B H8B2 109.3 . . ?
C9B C8B H8B2 109.3 . . ?
H8B1 C8B H8B2 108.0 . . ?
C10B C9B C8B 112.4(16) . . ?
C10B C9B C12B 112.9(10) . . ?
C8B C9B C12B 108.1(5) . . ?
C10B C9B H9B 107.7 . . ?
C8B C9B H9B 107.7 . . ?
C12B C9B H9B 107.7 . . ?
C13B C12B C9B 115.0(7) . . ?
C13B C12B H12C 108.5 . . ?
C9B C12B H12C 108.5 . . ?
C13B C12B H12D 108.5 . . ?
C9B C12B H12D 108.5 . . ?
H12C C12B H12D 107.5 . . ?
C12B C13B C14B 114.2(7) . . ?
C12B C13B H13C 108.7 . . ?
C14B C13B H13C 108.7 . . ?
C12B C13B H13D 108.7 . . ?
C14B C13B H13D 108.7 . . ?
H13C C13B H13D 107.6 . . ?
C15B C14B C13B 110.6(8) . . ?
C15B C14B H14C 109.5 . . ?
C13B C14B H14C 109.5 . . ?
C15B C14B H14D 109.5 . . ?
C13B C14B H14D 109.5 . . ?
H14C C14B H14D 108.1 . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C11B C10B C9B 114.3(14) . . ?
C11B C10B H10C 108.7 . . ?
C9B C10B H10C 108.7 . . ?
C11B C10B H10D 108.7 . . ?
C9B C10B H10D 108.7 . . ?
H10C C10B H10D 107.6 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C17 C16 C21 120.6(4) . . ?
C17 C16 P1 119.1(3) . . ?
C21 C16 P1 120.3(4) . . ?
C18 C17 C16 119.5(5) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.6(5) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.9(5) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 121.1(5) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C16 C21 C20 118.4(5) . . ?
C16 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C27 C22 C23 121.0(4) . . ?
C27 C22 P1 120.7(3) . . ?
C23 C22 P1 118.1(3) . . ?
C24 C23 C22 119.3(4) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C25 C24 C23 120.1(4) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 120.7(5) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 120.4(5) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 118.6(4) . . ?
C22 C27 H27 120.7 . . ?
C26 C27 H27 120.7 . . ?
C33 C28 C29 120.1(4) . . ?
C33 C28 P1 120.4(4) . . ?
C29 C28 P1 119.1(3) . . ?
C30 C29 C28 119.4(5) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C31 C30 C29 120.7(6) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 120.7(5) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C31 C32 C33 119.8(5) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C28 C33 C32 119.4(6) . . ?
C28 C33 H33 120.3 . . ?
C32 C33 H33 120.3 . . ?
Cl2S C1S Cl3S 112.2(3) . . ?
Cl2S C1S Cl1S 108.6(3) . . ?
Cl3S C1S Cl1S 110.5(3) . . ?
Cl2S C1S H1S 108.5 . . ?
Cl3S C1S H1S 108.5 . . ?
Cl1S C1S H1S 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
C7 N1 C1 O1 171.1(4) . . . . ?
C8A N1 C1 O1 0.4(6) . . . . ?
C8B N1 C1 O1 -6.4(9) . . . . ?
C7 N1 C1 C2 -10.6(6) . . . . ?
C8A N1 C1 C2 178.7(5) . . . . ?
C8B N1 C1 C2 171.9(8) . . . . ?
O1 C1 C2 C3 6.9(6) . . . . ?
N1 C1 C2 C3 -171.5(4) . . . . ?
O1 C1 C2 C6 -171.4(4) . . . 3_666 ?
N1 C1 C2 C6 10.3(6) . . . 3_666 ?
C6 C2 C3 C4 1.9(6) 3_666 . . . ?
C1 C2 C3 C4 -176.3(4) . . . . ?
C6 C2 C3 P1 -173.5(3) 3_666 . . . ?
C1 C2 C3 P1 8.3(5) . . . . ?
C22 P1 C3 C2 -78.9(4) . . . . ?
C16 P1 C3 C2 52.9(4) . . . . ?
C28 P1 C3 C2 166.4(4) . . . . ?
C22 P1 C3 C4 105.7(3) . . . . ?
C16 P1 C3 C4 -122.5(3) . . . . ?
C28 P1 C3 C4 -9.0(4) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
P1 C3 C4 C5 176.1(3) . . . . ?
C3 C4 C5 C6 -3.1(6) . . . . ?
C3 C4 C5 C7 177.6(4) . . . 3_666 ?
C4 C5 C6 C2 -177.7(4) . . . 3_666 ?
C7 C5 C6 C2 1.7(6) 3_666 . . 3_666 ?
C4 C5 C6 C6 3.3(7) . . . 3_666 ?
C7 C5 C6 C6 -177.3(5) 3_666 . . 3_666 ?
C1 N1 C7 O2 -177.1(4) . . . . ?
C8A N1 C7 O2 -6.7(7) . . . . ?
C8B N1 C7 O2 0.4(9) . . . . ?
C1 N1 C7 C5 4.6(6) . . . 3_666 ?
C8A N1 C7 C5 175.0(5) . . . 3_666 ?
C8B N1 C7 C5 -177.9(8) . . . 3_666 ?
C1 N1 C8A C9A -74.0(11) . . . . ?
C7 N1 C8A C9A 114.9(11) . . . . ?
N1 C8A C9A C10A -63.3(12) . . . . ?
N1 C8A C9A C12A 171.7(8) . . . . ?
C10A C9A C12A C13A 60.3(8) . . . . ?
C8A C9A C12A C13A -175.3(9) . . . . ?
C9A C12A C13A C14A 166.7(7) . . . . ?
C12A C13A C14A C15A -175.7(8) . . . . ?
C8A C9A C10A C11A -67.5(9) . . . . ?
C12A C9A C10A C11A 54.8(8) . . . . ?
C1 N1 C8B C9B -107(2) . . . . ?
C7 N1 C8B C9B 76(2) . . . . ?
N1 C8B C9B C10B 55(3) . . . . ?
N1 C8B C9B C12B -179.8(16) . . . . ?
C10B C9B C12B C13B 54.0(18) . . . . ?
C8B C9B C12B C13B -71(2) . . . . ?
C9B C12B C13B C14B -165.8(14) . . . . ?
C12B C13B C14B C15B -179.0(16) . . . . ?
C8B C9B C10B C11B 177.7(15) . . . . ?
C12B C9B C10B C11B 55.1(17) . . . . ?
C22 P1 C16 C17 154.7(3) . . . . ?
C28 P1 C16 C17 -86.7(4) . . . . ?
C3 P1 C16 C17 26.0(4) . . . . ?
C22 P1 C16 C21 -27.8(4) . . . . ?
C28 P1 C16 C21 90.7(4) . . . . ?
C3 P1 C16 C21 -156.6(3) . . . . ?
C21 C16 C17 C18 1.0(7) . . . . ?
P1 C16 C17 C18 178.4(4) . . . . ?
C16 C17 C18 C19 -1.0(8) . . . . ?
C17 C18 C19 C20 0.1(9) . . . . ?
C18 C19 C20 C21 0.9(8) . . . . ?
C17 C16 C21 C20 0.0(7) . . . . ?
P1 C16 C21 C20 -177.4(4) . . . . ?
C19 C20 C21 C16 -0.9(8) . . . . ?
C16 P1 C22 C27 -117.7(4) . . . . ?
C28 P1 C22 C27 123.6(4) . . . . ?
C3 P1 C22 C27 9.5(4) . . . . ?
C16 P1 C22 C23 66.9(4) . . . . ?
C28 P1 C22 C23 -51.7(4) . . . . ?
C3 P1 C22 C23 -165.8(3) . . . . ?
C27 C22 C23 C24 1.0(7) . . . . ?
P1 C22 C23 C24 176.3(4) . . . . ?
C22 C23 C24 C25 -1.0(7) . . . . ?
C23 C24 C25 C26 0.4(8) . . . . ?
C24 C25 C26 C27 0.3(9) . . . . ?
C23 C22 C27 C26 -0.3(7) . . . . ?
P1 C22 C27 C26 -175.5(4) . . . . ?
C25 C26 C27 C22 -0.3(8) . . . . ?
C22 P1 C28 C33 -33.4(4) . . . . ?
C16 P1 C28 C33 -159.3(3) . . . . ?
C3 P1 C28 C33 85.4(4) . . . . ?
C22 P1 C28 C29 153.6(3) . . . . ?
C16 P1 C28 C29 27.7(4) . . . . ?
C3 P1 C28 C29 -87.6(4) . . . . ?
C33 C28 C29 C30 0.0(7) . . . . ?
P1 C28 C29 C30 173.0(4) . . . . ?
C28 C29 C30 C31 -0.6(8) . . . . ?
C29 C30 C31 C32 0.9(8) . . . . ?
C30 C31 C32 C33 -0.5(8) . . . . ?
C29 C28 C33 C32 0.4(6) . . . . ?
P1 C28 C33 C32 -172.6(3) . . . . ?
C31 C32 C33 C28 -0.2(7) . . . . ?

_refine_diff_density_max         1.233
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.106

####################################################################### 
# 
# 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_h663
_database_code_depnum_ccdc_archive 'CCDC 1871422'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H66 F6 N2 O4 P3'
_chemical_formula_weight         1158.11

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   19.6640(5)
_cell_length_b                   19.9512(6)
_cell_length_c                   15.5025(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.1250(10)
_cell_angle_gamma                90
_cell_volume                     5673.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      5.39
_cell_measurement_theta_max      70.15

_exptl_crystal_description       Rod
_exptl_crystal_colour            Dark_Green
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             2428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.073
_exptl_absorpt_coefficient_mu    1.563
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4640
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24255
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.841
_diffrn_reflns_theta_max         70.162
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             5281
_reflns_number_gt                5046
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0671P)²+19.6497P] 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         5281
_refine_ls_number_parameters     462
_refine_ls_number_restraints     366
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1587
_refine_ls_wR_factor_gt          0.1540
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.57408(3) 0.29600(3) 0.56984(4) 0.01886(17) Uani 1 1 d . . . . .
N1 N 0.30949(10) 0.50320(10) 0.39859(14) 0.0195(4) Uani 1 1 d . . . . .
O1 O 0.30471(9) 0.39097(9) 0.42467(13) 0.0273(4) Uani 1 1 d . . . . .
O2 O 0.31214(9) 0.61724(8) 0.39039(12) 0.0221(4) Uani 1 1 d . . . . .
C1 C 0.53315(13) 0.37671(11) 0.53602(15) 0.0181(5) Uani 1 1 d . . . . .
C2 C 0.45763(13) 0.38055(12) 0.50058(15) 0.0186(5) Uani 1 1 d . . . . .
H2 H 0.4298 0.3408 0.4949 0.022 Uiso 1 1 calc R U . . .
C3 C 0.34238(13) 0.44129(12) 0.43213(16) 0.0201(5) Uani 1 1 d . . . . .
C4 C 0.42164(13) 0.44150(12) 0.47305(15) 0.0182(5) Uani 1 1 d . . . . .
C5 C 0.46130(12) 0.50153(11) 0.48131(15) 0.0167(5) Uani 1 1 d . . . . .
C6 C 0.42523(12) 0.56312(12) 0.45428(15) 0.0175(5) Uani 1 1 d . . . . .
C7 C 0.34649(13) 0.56417(12) 0.41349(15) 0.0183(5) Uani 1 1 d . . . . .
C8 C 0.23112(13) 0.50258(13) 0.34249(17) 0.0232(5) Uani 1 1 d D . . . .
H8A H 0.2120 0.5490 0.3349 0.028 Uiso 0.631(4) 1 calc R U P A 1
H8B H 0.2047 0.4762 0.3745 0.028 Uiso 0.631(4) 1 calc R U P A 1
H8C H 0.2060 0.5369 0.3664 0.028 Uiso 0.369(4) 1 calc R U P A 2
H8D H 0.2105 0.4583 0.3482 0.028 Uiso 0.369(4) 1 calc R U P A 2
C9 C 0.2180(2) 0.4714(2) 0.2457(3) 0.0280(9) Uani 0.631(4) 1 d D U P A 1
H9 H 0.2445 0.4276 0.2564 0.034 Uiso 0.631(4) 1 calc R U P A 1
C10 C 0.2514(2) 0.5156(2) 0.1915(3) 0.0324(10) Uani 0.631(4) 1 d D U P A 1
H10A H 0.2280 0.5603 0.1832 0.039 Uiso 0.631(4) 1 calc R U P A 1
H10B H 0.3039 0.5217 0.2283 0.039 Uiso 0.631(4) 1 calc R U P A 1
C11 C 0.2438(7) 0.4881(6) 0.0971(5) 0.0367(19) Uani 0.631(4) 1 d D U P A 1
H11A H 0.2626 0.4421 0.1038 0.055 Uiso 0.631(4) 1 calc R U P A 1
H11B H 0.2716 0.5161 0.0697 0.055 Uiso 0.631(4) 1 calc R U P A 1
H11C H 0.1923 0.4881 0.0568 0.055 Uiso 0.631(4) 1 calc R U P A 1
C12 C 0.1366(2) 0.4558(2) 0.1957(3) 0.0320(10) Uani 0.631(4) 1 d D U P A 1
H12A H 0.1311 0.4282 0.1405 0.038 Uiso 0.631(4) 1 calc R U P A 1
H12B H 0.1194 0.4287 0.2373 0.038 Uiso 0.631(4) 1 calc R U P A 1
C13 C 0.0878(2) 0.5169(2) 0.1651(4) 0.0366(10) Uani 0.631(4) 1 d D U P A 1
H13A H 0.1022 0.5425 0.1197 0.044 Uiso 0.631(4) 1 calc R U P A 1
H13B H 0.0953 0.5462 0.2193 0.044 Uiso 0.631(4) 1 calc R U P A 1
C14 C 0.0072(3) 0.4988(3) 0.1217(5) 0.0506(13) Uani 0.631(4) 1 d D U P A 1
H14A H -0.0071 0.4728 0.1669 0.061 Uiso 0.631(4) 1 calc R U P A 1
H14B H -0.0005 0.4699 0.0671 0.061 Uiso 0.631(4) 1 calc R U P A 1
C15 C -0.0417(3) 0.5608(3) 0.0921(6) 0.074(2) Uani 0.631(4) 1 d D U P A 1
H15A H -0.0318 0.5911 0.1450 0.110 Uiso 0.631(4) 1 calc R U P A 1
H15B H -0.0930 0.5470 0.0701 0.110 Uiso 0.631(4) 1 calc R U P A 1
H15C H -0.0316 0.5839 0.0423 0.110 Uiso 0.631(4) 1 calc R U P A 1
C9Y C 0.2170(3) 0.5170(4) 0.2391(4) 0.0231(13) Uani 0.369(4) 1 d D U P A 2
H9Y H 0.2360 0.5626 0.2334 0.028 Uiso 0.369(4) 1 calc R U P A 2
C10Y C 0.2566(4) 0.4650(4) 0.2019(5) 0.0305(15) Uani 0.369(4) 1 d D U P A 2
H10C H 0.3083 0.4636 0.2438 0.037 Uiso 0.369(4) 1 calc R U P A 2
H10D H 0.2353 0.4204 0.2044 0.037 Uiso 0.369(4) 1 calc R U P A 2
C11Y C 0.2546(13) 0.4761(11) 0.1040(9) 0.038(3) Uani 0.369(4) 1 d D U P A 2
H11D H 0.2047 0.4696 0.0601 0.057 Uiso 0.369(4) 1 calc R U P A 2
H11E H 0.2871 0.4440 0.0905 0.057 Uiso 0.369(4) 1 calc R U P A 2
H11F H 0.2706 0.5218 0.0982 0.057 Uiso 0.369(4) 1 calc R U P A 2
C12Y C 0.1354(4) 0.5153(4) 0.1857(6) 0.0359(16) Uani 0.369(4) 1 d D U P A 2
H12C H 0.1185 0.4686 0.1864 0.043 Uiso 0.369(4) 1 calc R U P A 2
H12D H 0.1269 0.5268 0.1206 0.043 Uiso 0.369(4) 1 calc R U P A 2
C13Y C 0.0876(4) 0.5608(5) 0.2188(6) 0.051(2) Uani 0.369(4) 1 d D U P A 2
H13C H 0.1103 0.6057 0.2314 0.062 Uiso 0.369(4) 1 calc R U P A 2
H13D H 0.0865 0.5429 0.2779 0.062 Uiso 0.369(4) 1 calc R U P A 2
C14Y C 0.0088(4) 0.5685(5) 0.1511(8) 0.061(2) Uani 0.369(4) 1 d D U P A 2
H14C H -0.0176 0.5980 0.1797 0.074 Uiso 0.369(4) 1 calc R U P A 2
H14D H 0.0097 0.5913 0.0947 0.074 Uiso 0.369(4) 1 calc R U P A 2
C15Y C -0.0339(6) 0.5032(6) 0.1223(9) 0.071(3) Uani 0.369(4) 1 d D U P A 2
H15D H -0.0079 0.4729 0.0951 0.106 Uiso 0.369(4) 1 calc R U P A 2
H15E H -0.0824 0.5128 0.0766 0.106 Uiso 0.369(4) 1 calc R U P A 2
H15F H -0.0390 0.4819 0.1767 0.106 Uiso 0.369(4) 1 calc R U P A 2
C1X C 0.49973(14) 0.23694(12) 0.54868(19) 0.0253(5) Uani 1 1 d . . . . .
C2X C 0.48317(16) 0.21035(13) 0.6217(2) 0.0329(6) Uani 1 1 d . . . . .
H2X H 0.5127 0.2210 0.6836 0.039 Uiso 1 1 calc R U . . .
C3X C 0.42330(18) 0.16803(16) 0.6041(3) 0.0451(8) Uani 1 1 d . . . . .
H3X H 0.4123 0.1493 0.6539 0.054 Uiso 1 1 calc R U . . .
C4X C 0.37979(17) 0.15344(16) 0.5133(3) 0.0497(9) Uani 1 1 d . . . . .
H4X H 0.3385 0.1252 0.5012 0.060 Uiso 1 1 calc R U . . .
C5X C 0.39602(17) 0.17958(16) 0.4410(3) 0.0475(9) Uani 1 1 d . . . . .
H5X H 0.3657 0.1695 0.3792 0.057 Uiso 1 1 calc R U . . .
C6X C 0.45658(16) 0.22069(14) 0.4580(2) 0.0354(6) Uani 1 1 d . . . . .
H6X H 0.4685 0.2376 0.4079 0.043 Uiso 1 1 calc R U . . .
C1Y C 0.62392(13) 0.29433(12) 0.69288(17) 0.0203(5) Uani 1 1 d . . . . .
C2Y C 0.67913(14) 0.24838(13) 0.73616(18) 0.0256(5) Uani 1 1 d . . . . .
H2Y H 0.6931 0.2162 0.7004 0.031 Uiso 1 1 calc R U . . .
C3Y C 0.71378(15) 0.24978(14) 0.83186(19) 0.0312(6) Uani 1 1 d . . . . .
H3Y H 0.7511 0.2183 0.8616 0.037 Uiso 1 1 calc R U . . .
C4Y C 0.69378(15) 0.29710(14) 0.88391(18) 0.0295(6) Uani 1 1 d . . . . .
H4Y H 0.7180 0.2983 0.9491 0.035 Uiso 1 1 calc R U . . .
C5Y C 0.63859(14) 0.34259(13) 0.84125(18) 0.0256(5) Uani 1 1 d . . . . .
H5Y H 0.6250 0.3748 0.8772 0.031 Uiso 1 1 calc R U . . .
C6Y C 0.60315(13) 0.34100(12) 0.74576(17) 0.0225(5) Uani 1 1 d . . . . .
H6Y H 0.5648 0.3717 0.7165 0.027 Uiso 1 1 calc R U . . .
C1Z C 0.62004(13) 0.26771(13) 0.49496(17) 0.0236(5) Uani 1 1 d . . . . .
C2Z C 0.65074(15) 0.20336(14) 0.50585(19) 0.0298(6) Uani 1 1 d . . . . .
H2Z H 0.6499 0.1753 0.5550 0.036 Uiso 1 1 calc R U . . .
C3Z C 0.68224(15) 0.18110(15) 0.4444(2) 0.0340(6) Uani 1 1 d . . . . .
H3Z H 0.7051 0.1384 0.4532 0.041 Uiso 1 1 calc R U . . .
C4Z C 0.68083(16) 0.22029(16) 0.3707(2) 0.0357(7) Uani 1 1 d . . . . .
H4Z H 0.7023 0.2044 0.3287 0.043 Uiso 1 1 calc R U . . .
C5Z C 0.64812(16) 0.28288(15) 0.3576(2) 0.0334(6) Uani 1 1 d . . . . .
H5Z H 0.6460 0.3093 0.3058 0.040 Uiso 1 1 calc R U . . .
C6Z C 0.61835(15) 0.30706(14) 0.42057(18) 0.0283(6) Uani 1 1 d . . . . .
H6Z H 0.5969 0.3504 0.4125 0.034 Uiso 1 1 calc R U . . .
P2 P 0.5000 0.4582(3) 0.2500 0.0388(3) Uani 0.5 2 d DS TU P B 1
F1 F 0.4847(3) 0.52367(17) 0.2986(3) 0.0459(7) Uani 0.5 1 d D U P B 1
F2 F 0.5789(2) 0.4511(2) 0.3391(4) 0.0390(8) Uani 0.5 1 d D U P B 1
F3 F 0.4659(3) 0.4104(2) 0.3038(3) 0.0360(8) Uani 0.5 1 d D U P B 1
P2Y P 0.5000 0.4594(3) 0.2500 0.0388(3) Uani 0.5 2 d DS TU P C 2
F1Y F 0.4485(2) 0.50619(17) 0.2903(3) 0.0418(7) Uani 0.5 1 d D U P C 2
F2Y F 0.5656(2) 0.4659(2) 0.3435(4) 0.0428(8) Uani 0.5 1 d D U P C 2
F3Y F 0.4672(3) 0.39501(18) 0.2860(3) 0.0338(8) Uani 0.5 1 d D U P C 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.792(2) . ?
P1 C1Z 1.800(2) . ?
P1 C1Y 1.803(2) . ?
P1 C1X 1.813(3) . ?
N1 C7 1.393(3) . ?
N1 C3 1.404(3) . ?
N1 C8 1.471(3) . ?
O1 C3 1.228(3) . ?
O2 C7 1.237(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.430(3) 5_666 ?
C2 C4 1.394(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.456(3) . ?
C4 C5 1.410(3) . ?
C5 C6 1.405(3) . ?
C5 C5 1.421(4) 5_666 ?
C6 C1 1.430(3) 5_666 ?
C6 C7 1.446(3) . ?
C8 C9Y 1.551(6) . ?
C8 C9 1.557(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 H8C 0.9900 . ?
C8 H8D 0.9900 . ?
C9 C10 1.523(5) . ?
C9 C12 1.538(5) . ?
C9 H9 1.0000 . ?
C10 C11 1.519(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.516(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.526(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.532(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C9Y C12Y 1.518(7) . ?
C9Y C10Y 1.531(7) . ?
C9Y H9Y 1.0000 . ?
C10Y C11Y 1.520(9) . ?
C10Y H10C 0.9900 . ?
C10Y H10D 0.9900 . ?
C11Y H11D 0.9800 . ?
C11Y H11E 0.9800 . ?
C11Y H11F 0.9800 . ?
C12Y C13Y 1.522(8) . ?
C12Y H12C 0.9900 . ?
C12Y H12D 0.9900 . ?
C13Y C14Y 1.533(8) . ?
C13Y H13C 0.9900 . ?
C13Y H13D 0.9900 . ?
C14Y C15Y 1.527(9) . ?
C14Y H14C 0.9900 . ?
C14Y H14D 0.9900 . ?
C15Y H15D 0.9800 . ?
C15Y H15E 0.9800 . ?
C15Y H15F 0.9800 . ?
C1X C2X 1.391(4) . ?
C1X C6X 1.394(4) . ?
C2X C3X 1.393(4) . ?
C2X H2X 0.9500 . ?
C3X C4X 1.388(5) . ?
C3X H3X 0.9500 . ?
C4X C5X 1.374(6) . ?
C4X H4X 0.9500 . ?
C5X C6X 1.391(5) . ?
C5X H5X 0.9500 . ?
C6X H6X 0.9500 . ?
C1Y C2Y 1.394(3) . ?
C1Y C6Y 1.396(3) . ?
C2Y C3Y 1.392(4) . ?
C2Y H2Y 0.9500 . ?
C3Y C4Y 1.388(4) . ?
C3Y H3Y 0.9500 . ?
C4Y C5Y 1.386(4) . ?
C4Y H4Y 0.9500 . ?
C5Y C6Y 1.391(4) . ?
C5Y H5Y 0.9500 . ?
C6Y H6Y 0.9500 . ?
C1Z C6Z 1.386(4) . ?
C1Z C2Z 1.403(4) . ?
C2Z C3Z 1.383(4) . ?
C2Z H2Z 0.9500 . ?
C3Z C4Z 1.377(4) . ?
C3Z H3Z 0.9500 . ?
C4Z C5Z 1.386(4) . ?
C4Z H4Z 0.9500 . ?
C5Z C6Z 1.392(4) . ?
C5Z H5Z 0.9500 . ?
C6Z H6Z 0.9500 . ?
P2 F3 1.568(4) . ?
P2 F3 1.568(4) 2_655 ?
P2 F1 1.590(5) . ?
P2 F1 1.590(5) 2_655 ?
P2 F2 1.671(4) 2_655 ?
P2 F2 1.671(4) . ?
P2Y F2Y 1.560(4) . ?
P2Y F2Y 1.560(4) 2_655 ?
P2Y F3Y 1.624(5) . ?
P2Y F3Y 1.624(5) 2_655 ?
P2Y F1Y 1.656(4) . ?
P2Y F1Y 1.656(4) 2_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C1Z 111.72(11) . . ?
C1 P1 C1Y 109.98(11) . . ?
C1Z P1 C1Y 117.94(11) . . ?
C1 P1 C1X 106.45(11) . . ?
C1Z P1 C1X 103.83(12) . . ?
C1Y P1 C1X 105.95(12) . . ?
C7 N1 C3 124.28(19) . . ?
C7 N1 C8 118.58(19) . . ?
C3 N1 C8 117.13(19) . . ?
C2 C1 C6 119.0(2) . 5_666 ?
C2 C1 P1 117.99(18) . . ?
C6 C1 P1 122.95(17) 5_666 . ?
C1 C2 C4 121.5(2) . . ?
C1 C2 H2 119.3 . . ?
C4 C2 H2 119.3 . . ?
O1 C3 N1 120.2(2) . . ?
O1 C3 C4 123.9(2) . . ?
N1 C3 C4 115.9(2) . . ?
C2 C4 C5 120.7(2) . . ?
C2 C4 C3 118.5(2) . . ?
C5 C4 C3 120.8(2) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 C5 120.7(3) . 5_666 ?
C4 C5 C5 118.5(3) . 5_666 ?
C5 C6 C1 119.6(2) . 5_666 ?
C5 C6 C7 119.3(2) . . ?
C1 C6 C7 121.0(2) 5_666 . ?
O2 C7 N1 120.1(2) . . ?
O2 C7 C6 121.7(2) . . ?
N1 C7 C6 118.2(2) . . ?
N1 C8 C9Y 111.6(3) . . ?
N1 C8 C9 110.4(2) . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N1 C8 H8C 109.3 . . ?
C9Y C8 H8C 109.3 . . ?
N1 C8 H8D 109.3 . . ?
C9Y C8 H8D 109.3 . . ?
H8C C8 H8D 108.0 . . ?
C10 C9 C12 114.6(3) . . ?
C10 C9 C8 110.2(3) . . ?
C12 C9 C8 110.4(3) . . ?
C10 C9 H9 107.1 . . ?
C12 C9 H9 107.1 . . ?
C8 C9 H9 107.1 . . ?
C11 C10 C9 114.2(6) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C9 115.0(4) . . ?
C13 C12 H12A 108.5 . . ?
C9 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C9 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 C14 112.8(4) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 112.4(4) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12Y C9Y C10Y 111.2(6) . . ?
C12Y C9Y C8 108.7(5) . . ?
C10Y C9Y C8 109.8(5) . . ?
C12Y C9Y H9Y 109.1 . . ?
C10Y C9Y H9Y 109.1 . . ?
C8 C9Y H9Y 109.1 . . ?
C11Y C10Y C9Y 116.4(8) . . ?
C11Y C10Y H10C 108.2 . . ?
C9Y C10Y H10C 108.2 . . ?
C11Y C10Y H10D 108.2 . . ?
C9Y C10Y H10D 108.2 . . ?
H10C C10Y H10D 107.3 . . ?
C10Y C11Y H11D 109.5 . . ?
C10Y C11Y H11E 109.5 . . ?
H11D C11Y H11E 109.5 . . ?
C10Y C11Y H11F 109.5 . . ?
H11D C11Y H11F 109.5 . . ?
H11E C11Y H11F 109.5 . . ?
C9Y C12Y C13Y 117.6(6) . . ?
C9Y C12Y H12C 107.9 . . ?
C13Y C12Y H12C 107.9 . . ?
C9Y C12Y H12D 107.9 . . ?
C13Y C12Y H12D 107.9 . . ?
H12C C12Y H12D 107.2 . . ?
C12Y C13Y C14Y 115.0(6) . . ?
C12Y C13Y H13C 108.5 . . ?
C14Y C13Y H13C 108.5 . . ?
C12Y C13Y H13D 108.5 . . ?
C14Y C13Y H13D 108.5 . . ?
H13C C13Y H13D 107.5 . . ?
C15Y C14Y C13Y 115.4(7) . . ?
C15Y C14Y H14C 108.4 . . ?
C13Y C14Y H14C 108.4 . . ?
C15Y C14Y H14D 108.4 . . ?
C13Y C14Y H14D 108.4 . . ?
H14C C14Y H14D 107.5 . . ?
C14Y C15Y H15D 109.5 . . ?
C14Y C15Y H15E 109.5 . . ?
H15D C15Y H15E 109.5 . . ?
C14Y C15Y H15F 109.5 . . ?
H15D C15Y H15F 109.5 . . ?
H15E C15Y H15F 109.5 . . ?
C2X C1X C6X 119.8(3) . . ?
C2X C1X P1 120.7(2) . . ?
C6X C1X P1 119.4(2) . . ?
C1X C2X C3X 120.0(3) . . ?
C1X C2X H2X 120.0 . . ?
C3X C2X H2X 120.0 . . ?
C4X C3X C2X 119.6(3) . . ?
C4X C3X H3X 120.2 . . ?
C2X C3X H3X 120.2 . . ?
C5X C4X C3X 120.5(3) . . ?
C5X C4X H4X 119.8 . . ?
C3X C4X H4X 119.8 . . ?
C4X C5X C6X 120.3(3) . . ?
C4X C5X H5X 119.9 . . ?
C6X C5X H5X 119.9 . . ?
C5X C6X C1X 119.7(3) . . ?
C5X C6X H6X 120.1 . . ?
C1X C6X H6X 120.1 . . ?
C2Y C1Y C6Y 119.9(2) . . ?
C2Y C1Y P1 123.59(19) . . ?
C6Y C1Y P1 116.52(18) . . ?
C3Y C2Y C1Y 119.8(2) . . ?
C3Y C2Y H2Y 120.1 . . ?
C1Y C2Y H2Y 120.1 . . ?
C4Y C3Y C2Y 120.1(2) . . ?
C4Y C3Y H3Y 120.0 . . ?
C2Y C3Y H3Y 120.0 . . ?
C5Y C4Y C3Y 120.3(2) . . ?
C5Y C4Y H4Y 119.8 . . ?
C3Y C4Y H4Y 119.8 . . ?
C4Y C5Y C6Y 119.9(2) . . ?
C4Y C5Y H5Y 120.0 . . ?
C6Y C5Y H5Y 120.0 . . ?
C5Y C6Y C1Y 120.0(2) . . ?
C5Y C6Y H6Y 120.0 . . ?
C1Y C6Y H6Y 120.0 . . ?
C6Z C1Z C2Z 119.9(2) . . ?
C6Z C1Z P1 119.48(19) . . ?
C2Z C1Z P1 120.3(2) . . ?
C3Z C2Z C1Z 119.4(3) . . ?
C3Z C2Z H2Z 120.3 . . ?
C1Z C2Z H2Z 120.3 . . ?
C4Z C3Z C2Z 120.6(3) . . ?
C4Z C3Z H3Z 119.7 . . ?
C2Z C3Z H3Z 119.7 . . ?
C3Z C4Z C5Z 120.2(2) . . ?
C3Z C4Z H4Z 119.9 . . ?
C5Z C4Z H4Z 119.9 . . ?
C4Z C5Z C6Z 120.0(3) . . ?
C4Z C5Z H5Z 120.0 . . ?
C6Z C5Z H5Z 120.0 . . ?
C1Z C6Z C5Z 119.8(2) . . ?
C1Z C6Z H6Z 120.1 . . ?
C5Z C6Z H6Z 120.1 . . ?
F3 P2 F3 105.1(5) . 2_655 ?
F3 P2 F1 93.3(2) . . ?
F3 P2 F1 160.4(4) 2_655 . ?
F3 P2 F1 160.4(4) . 2_655 ?
F3 P2 F1 93.3(2) 2_655 2_655 ?
F1 P2 F1 69.5(4) . 2_655 ?
F3 P2 F2 86.6(3) . 2_655 ?
F3 P2 F2 87.5(3) 2_655 2_655 ?
F1 P2 F2 100.5(3) . 2_655 ?
F1 P2 F2 87.5(2) 2_655 2_655 ?
F3 P2 F2 87.5(3) . . ?
F3 P2 F2 86.6(3) 2_655 . ?
F1 P2 F2 87.5(2) . . ?
F1 P2 F2 100.5(3) 2_655 . ?
F2 P2 F2 170.4(5) 2_655 . ?
F2Y P2Y F2Y 170.5(5) . 2_655 ?
F2Y P2Y F3Y 92.5(3) . . ?
F2Y P2Y F3Y 95.0(3) 2_655 . ?
F2Y P2Y F3Y 95.0(3) . 2_655 ?
F2Y P2Y F3Y 92.5(3) 2_655 2_655 ?
F3Y P2Y F3Y 75.5(4) . 2_655 ?
F2Y P2Y F1Y 91.0(3) . . ?
F2Y P2Y F1Y 83.7(3) 2_655 . ?
F3Y P2Y F1Y 86.75(19) . . ?
F3Y P2Y F1Y 161.5(4) 2_655 . ?
F2Y P2Y F1Y 83.7(3) . 2_655 ?
F2Y P2Y F1Y 91.0(3) 2_655 2_655 ?
F3Y P2Y F1Y 161.5(4) . 2_655 ?
F3Y P2Y F1Y 86.75(19) 2_655 2_655 ?
F1Y P2Y F1Y 111.4(5) . 2_655 ?

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
C1Z P1 C1 C2 111.67(19) . . . . ?
C1Y P1 C1 C2 -115.38(19) . . . . ?
C1X P1 C1 C2 -1.0(2) . . . . ?
C1Z P1 C1 C6 -69.6(2) . . . 5_666 ?
C1Y P1 C1 C6 63.3(2) . . . 5_666 ?
C1X P1 C1 C6 177.67(19) . . . 5_666 ?
C6 C1 C2 C4 1.0(3) 5_666 . . . ?
P1 C1 C2 C4 179.74(17) . . . . ?
C7 N1 C3 O1 172.0(2) . . . . ?
C8 N1 C3 O1 -9.3(3) . . . . ?
C7 N1 C3 C4 -9.1(3) . . . . ?
C8 N1 C3 C4 169.50(19) . . . . ?
C1 C2 C4 C5 -0.6(3) . . . . ?
C1 C2 C4 C3 176.9(2) . . . . ?
O1 C3 C4 C2 4.0(4) . . . . ?
N1 C3 C4 C2 -174.8(2) . . . . ?
O1 C3 C4 C5 -178.5(2) . . . . ?
N1 C3 C4 C5 2.7(3) . . . . ?
C2 C4 C5 C6 -179.5(2) . . . . ?
C3 C4 C5 C6 3.0(3) . . . . ?
C2 C4 C5 C5 -0.3(4) . . . 5_666 ?
C3 C4 C5 C5 -177.7(2) . . . 5_666 ?
C4 C5 C6 C1 179.6(2) . . . 5_666 ?
C5 C5 C6 C1 0.4(4) 5_666 . . 5_666 ?
C4 C5 C6 C7 -2.9(3) . . . . ?
C5 C5 C6 C7 177.8(2) 5_666 . . . ?
C3 N1 C7 O2 -172.0(2) . . . . ?
C8 N1 C7 O2 9.4(3) . . . . ?
C3 N1 C7 C6 9.4(3) . . . . ?
C8 N1 C7 C6 -169.23(19) . . . . ?
C5 C6 C7 O2 178.4(2) . . . . ?
C1 C6 C7 O2 -4.1(3) 5_666 . . . ?
C5 C6 C7 N1 -3.0(3) . . . . ?
C1 C6 C7 N1 174.5(2) 5_666 . . . ?
C7 N1 C8 C9Y 70.1(4) . . . . ?
C3 N1 C8 C9Y -108.6(3) . . . . ?
C7 N1 C8 C9 106.8(3) . . . . ?
C3 N1 C8 C9 -71.9(3) . . . . ?
N1 C8 C9 C10 -65.3(4) . . . . ?
N1 C8 C9 C12 167.1(3) . . . . ?
C12 C9 C10 C11 -56.9(7) . . . . ?
C8 C9 C10 C11 177.9(6) . . . . ?
C10 C9 C12 C13 -55.8(5) . . . . ?
C8 C9 C12 C13 69.3(5) . . . . ?
C9 C12 C13 C14 -176.1(4) . . . . ?
C12 C13 C14 C15 179.3(5) . . . . ?
N1 C8 C9Y C12Y 179.8(4) . . . . ?
N1 C8 C9Y C10Y 58.0(6) . . . . ?
C12Y C9Y C10Y C11Y 65.7(14) . . . . ?
C8 C9Y C10Y C11Y -174.1(12) . . . . ?
C10Y C9Y C12Y C13Y 175.8(7) . . . . ?
C8 C9Y C12Y C13Y 54.9(9) . . . . ?
C9Y C12Y C13Y C14Y 167.3(8) . . . . ?
C12Y C13Y C14Y C15Y 57.0(14) . . . . ?
C1 P1 C1X C2X -105.8(2) . . . . ?
C1Z P1 C1X C2X 136.2(2) . . . . ?
C1Y P1 C1X C2X 11.3(2) . . . . ?
C1 P1 C1X C6X 71.0(2) . . . . ?
C1Z P1 C1X C6X -47.0(2) . . . . ?
C1Y P1 C1X C6X -171.9(2) . . . . ?
C6X C1X C2X C3X -0.5(4) . . . . ?
P1 C1X C2X C3X 176.3(2) . . . . ?
C1X C2X C3X C4X -1.0(4) . . . . ?
C2X C3X C4X C5X 1.0(5) . . . . ?
C3X C4X C5X C6X 0.4(5) . . . . ?
C4X C5X C6X C1X -1.8(4) . . . . ?
C2X C1X C6X C5X 1.9(4) . . . . ?
P1 C1X C6X C5X -175.0(2) . . . . ?
C1 P1 C1Y C2Y -159.3(2) . . . . ?
C1Z P1 C1Y C2Y -29.6(3) . . . . ?
C1X P1 C1Y C2Y 86.1(2) . . . . ?
C1 P1 C1Y C6Y 22.7(2) . . . . ?
C1Z P1 C1Y C6Y 152.38(19) . . . . ?
C1X P1 C1Y C6Y -92.0(2) . . . . ?
C6Y C1Y C2Y C3Y -0.7(4) . . . . ?
P1 C1Y C2Y C3Y -178.6(2) . . . . ?
C1Y C2Y C3Y C4Y -0.5(4) . . . . ?
C2Y C3Y C4Y C5Y 0.9(4) . . . . ?
C3Y C4Y C5Y C6Y -0.2(4) . . . . ?
C4Y C5Y C6Y C1Y -1.0(4) . . . . ?
C2Y C1Y C6Y C5Y 1.4(4) . . . . ?
P1 C1Y C6Y C5Y 179.53(19) . . . . ?
C1 P1 C1Z C6Z -1.8(3) . . . . ?
C1Y P1 C1Z C6Z -130.7(2) . . . . ?
C1X P1 C1Z C6Z 112.5(2) . . . . ?
C1 P1 C1Z C2Z -175.1(2) . . . . ?
C1Y P1 C1Z C2Z 56.0(3) . . . . ?
C1X P1 C1Z C2Z -60.8(2) . . . . ?
C6Z C1Z C2Z C3Z 3.1(4) . . . . ?
P1 C1Z C2Z C3Z 176.4(2) . . . . ?
C1Z C2Z C3Z C4Z -2.9(4) . . . . ?
C2Z C3Z C4Z C5Z 0.4(5) . . . . ?
C3Z C4Z C5Z C6Z 1.8(5) . . . . ?
C2Z C1Z C6Z C5Z -0.9(4) . . . . ?
P1 C1Z C6Z C5Z -174.3(2) . . . . ?
C4Z C5Z C6Z C1Z -1.5(4) . . . . ?

_refine_diff_density_max         0.638
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_I122
_database_code_depnum_ccdc_archive 'CCDC 1871424'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H66 Cl N2 O7.33 P2'
_chemical_formula_weight         1101.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 '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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

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

_cell_length_a                   24.8062(9)
_cell_length_b                   24.8062(9)
_cell_length_c                   30.0418(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     16009.5(13)
_cell_formula_units_Z            9
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9763
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      70.20

_exptl_crystal_description       Block
_exptl_crystal_colour            Dark_red
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.029
_exptl_crystal_F_000             5235
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.217
_exptl_absorpt_coefficient_mu    1.268
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6203
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49333
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.528
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_full        66.594
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             6201
_reflns_number_gt                5456
_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_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] 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         6201
_refine_ls_number_parameters     407
_refine_ls_number_restraints     105
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.1377
_refine_ls_wR_factor_ref         0.4169
_refine_ls_wR_factor_gt          0.4022
_refine_ls_goodness_of_fit_ref   2.015
_refine_ls_restrained_S_all      2.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.57570(4) 0.00179(5) 0.13022(3) 0.0463(4) Uani 1 1 d . . . . .
Cl1 Cl 0.3333 0.6667 0.22108(17) 0.0906(14) Uani 0.5 3 d S T P A 1
Cl2 Cl 0.4500(5) 0.5914(6) 0.3182(5) 0.108(3) Uani 0.1667 1 d . . P B 2
Cl3 Cl 0.1296(6) 0.4900(9) 0.0016(4) 0.118(4) Uani 0.1667 1 d . . P C 3
O1 O 0.39322(15) 0.04406(18) 0.08456(9) 0.0618(8) Uani 1 1 d . . . . .
O2 O 0.37820(12) 0.04203(13) -0.06654(8) 0.0501(7) Uani 1 1 d . . . . .
N1 N 0.38311(14) 0.03964(15) 0.00920(10) 0.0475(8) Uani 1 1 d . . . . .
C1 C 0.41111(18) 0.0353(2) 0.04876(12) 0.0492(9) Uani 1 1 d . . . . .
C2 C 0.40121(16) 0.03268(17) -0.03298(11) 0.0433(8) Uani 1 1 d . . . . .
C3 C 0.44761(16) 0.01350(17) -0.03718(11) 0.0440(8) Uani 1 1 d . . . . .
C4 C 0.47668(15) 0.00857(16) 0.00168(11) 0.0420(8) Uani 1 1 d . . . . .
C5 C 0.45971(16) 0.01990(17) 0.04376(11) 0.0458(8) Uani 1 1 d . . . . .
C6 C 0.33228(19) 0.0533(2) 0.01345(13) 0.0521(9) Uani 1 1 d . . . . .
H6A H 0.3267 0.0699 -0.0151 0.062 Uiso 1 1 calc R U . . .
H6B H 0.3429 0.0855 0.0366 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2698(3) -0.0074(3) 0.0264(2) 0.0841(16) Uani 1 1 d . . . . .
H7 H 0.2770 -0.0221 0.0556 0.101 Uiso 1 1 calc R U . D 1
C8 C 0.2509(3) -0.0596(3) -0.0062(3) 0.096(2) Uani 1 1 d . . . . .
H8A H 0.2870 -0.0652 -0.0125 0.115 Uiso 1 1 calc R U . . .
H8B H 0.2380 -0.0490 -0.0345 0.115 Uiso 1 1 calc R U . . .
C9 C 0.1973(5) -0.1203(4) 0.0121(3) 0.135(4) Uani 1 1 d . . . . .
H9A H 0.1767 -0.1495 -0.0125 0.203 Uiso 1 1 calc R U . . .
H9B H 0.1672 -0.1117 0.0270 0.203 Uiso 1 1 calc R U . . .
H9C H 0.2135 -0.1385 0.0335 0.203 Uiso 1 1 calc R U . . .
C10 C 0.2185(4) 0.0081(4) 0.0336(4) 0.075(2) Uani 0.640(11) 1 d D U P E 1
H10A H 0.2143 0.0278 0.0062 0.090 Uiso 0.640(11) 1 calc R U P E 1
H10B H 0.1788 -0.0313 0.0379 0.090 Uiso 0.640(11) 1 calc R U P E 1
C11 C 0.2274(6) 0.0504(6) 0.0723(5) 0.090(2) Uani 0.640(11) 1 d D U P E 1
H11A H 0.2660 0.0907 0.0675 0.107 Uiso 0.640(11) 1 calc R U P E 1
H11B H 0.2329 0.0316 0.0997 0.107 Uiso 0.640(11) 1 calc R U P E 1
C12 C 0.1733(6) 0.0624(6) 0.0791(6) 0.105(3) Uani 0.640(11) 1 d D U P E 1
H12A H 0.1742 0.0905 0.0553 0.125 Uiso 0.640(11) 1 calc R U P E 1
H12B H 0.1335 0.0226 0.0765 0.125 Uiso 0.640(11) 1 calc R U P E 1
C13 C 0.1758(8) 0.0893(8) 0.1208(6) 0.126(4) Uani 0.640(11) 1 d D U P E 1
H13A H 0.1404 0.0963 0.1238 0.189 Uiso 0.640(11) 1 calc R U P E 1
H13B H 0.1741 0.0613 0.1445 0.189 Uiso 0.640(11) 1 calc R U P E 1
H13C H 0.2147 0.1292 0.1233 0.189 Uiso 0.640(11) 1 calc R U P E 1
C10X C 0.2233(8) 0.0279(9) 0.0111(7) 0.087(3) Uani 0.360(11) 1 d D U P E 2
H10C H 0.2471 0.0655 -0.0074 0.105 Uiso 0.360(11) 1 calc R U P E 2
H10D H 0.1845 -0.0019 -0.0045 0.105 Uiso 0.360(11) 1 calc R U P E 2
C11X C 0.2101(11) 0.0438(12) 0.0571(8) 0.094(3) Uani 0.360(11) 1 d D U P E 2
H11C H 0.2479 0.0800 0.0694 0.113 Uiso 0.360(11) 1 calc R U P E 2
H11D H 0.1970 0.0080 0.0775 0.113 Uiso 0.360(11) 1 calc R U P E 2
C12X C 0.1568(10) 0.0596(11) 0.0518(10) 0.108(3) Uani 0.360(11) 1 d D U P E 2
H12C H 0.1561 0.0741 0.0212 0.129 Uiso 0.360(11) 1 calc R U P E 2
H12D H 0.1158 0.0229 0.0585 0.129 Uiso 0.360(11) 1 calc R U P E 2
C13X C 0.1717(13) 0.1075(12) 0.0830(11) 0.123(4) Uani 0.360(11) 1 d D U P E 2
H13D H 0.1402 0.1203 0.0818 0.184 Uiso 0.360(11) 1 calc R U P E 2
H13E H 0.1726 0.0923 0.1129 0.184 Uiso 0.360(11) 1 calc R U P E 2
H13F H 0.2126 0.1431 0.0759 0.184 Uiso 0.360(11) 1 calc R U P E 2
C14 C 0.49049(17) 0.01672(18) 0.08170(12) 0.0471(8) Uani 1 1 d . . . . .
H14 H 0.4798 0.0259 0.1099 0.057 Uiso 1 1 calc R U . . .
C15 C 0.53644(16) 0.00046(17) 0.07904(11) 0.0449(8) Uani 1 1 d . . . . .
C16 C 0.55284(18) -0.0741(2) 0.15189(13) 0.0545(10) Uani 1 1 d . . . . .
C17 C 0.5160(2) -0.1271(2) 0.12791(17) 0.0643(11) Uani 1 1 d . . . . .
H17 H 0.5074 -0.1244 0.0974 0.077 Uiso 1 1 calc R U . . .
C18 C 0.4911(3) -0.1854(3) 0.1486(3) 0.0844(17) Uani 1 1 d . . . . .
H18 H 0.4650 -0.2223 0.1324 0.101 Uiso 1 1 calc R U . . .
C19 C 0.5050(3) -0.1886(3) 0.1934(2) 0.088(2) Uani 1 1 d . . . . .
H19 H 0.4870 -0.2277 0.2080 0.105 Uiso 1 1 calc R U . . .
C20 C 0.5438(3) -0.1361(4) 0.2157(2) 0.0856(19) Uani 1 1 d . . . . .
H20 H 0.5550 -0.1392 0.2454 0.103 Uiso 1 1 calc R U . . .
C21 C 0.5676(3) -0.0779(3) 0.19655(15) 0.0706(13) Uani 1 1 d . . . . .
H21 H 0.5935 -0.0413 0.2132 0.085 Uiso 1 1 calc R U . . .
C22 C 0.65826(17) 0.0534(2) 0.12540(12) 0.0532(10) Uani 1 1 d . . . . .
C23 C 0.6995(2) 0.0412(3) 0.14942(16) 0.0668(12) Uani 1 1 d . . . . .
H23 H 0.6848 0.0057 0.1681 0.080 Uiso 1 1 calc R U . . .
C24 C 0.7633(3) 0.0835(4) 0.1449(2) 0.0884(19) Uani 1 1 d . . . . .
H24 H 0.7924 0.0761 0.1603 0.106 Uiso 1 1 calc R U . . .
C25 C 0.7838(2) 0.1336(4) 0.1194(2) 0.103(3) Uani 1 1 d . . . . .
H25 H 0.8274 0.1616 0.1175 0.124 Uiso 1 1 calc R U . . .
C26 C 0.7437(3) 0.1465(3) 0.0954(2) 0.093(2) Uani 1 1 d . . . . .
H26 H 0.7595 0.1826 0.0772 0.112 Uiso 1 1 calc R U . . .
C27 C 0.6791(2) 0.1049(3) 0.09854(16) 0.0696(13) Uani 1 1 d . . . . .
H27 H 0.6505 0.1124 0.0825 0.084 Uiso 1 1 calc R U . . .
C28 C 0.54800(18) 0.0362(2) 0.17120(11) 0.0536(10) Uani 1 1 d . . . . .
C29 C 0.5809(2) 0.0997(2) 0.17943(15) 0.0631(11) Uani 1 1 d . . . . .
H29 H 0.6204 0.1252 0.1661 0.076 Uiso 1 1 calc R U . . .
C30 C 0.5550(3) 0.1255(3) 0.2076(2) 0.0813(15) Uani 1 1 d . . . . .
H30 H 0.5776 0.1688 0.2140 0.098 Uiso 1 1 calc R U . . .
C31 C 0.4973(3) 0.0891(3) 0.22630(17) 0.0784(15) Uani 1 1 d . . . . .
H31 H 0.4795 0.1074 0.2446 0.094 Uiso 1 1 calc R U . . .
C32 C 0.4655(2) 0.0264(3) 0.21858(14) 0.0707(14) Uani 1 1 d . . . . .
H32 H 0.4261 0.0013 0.2322 0.085 Uiso 1 1 calc R U . . .
C33 C 0.4901(2) -0.0010(3) 0.19097(12) 0.0604(11) Uani 1 1 d . . . . .
H33 H 0.4676 -0.0446 0.1857 0.072 Uiso 1 1 calc R U . . .
O1W O 0.1695(5) 0.6287(4) 0.0150(3) 0.091(2) Uiso 0.5 1 d . . P F 1
O4W O 0.2819(8) 0.4878(8) 0.3305(6) 0.135(4) Uiso 0.5 1 d . . P G 2
O2W O 0.4767(9) 0.6660(9) 0.4336(7) 0.158(6) Uiso 0.5 1 d . . P . .
O3W O 0.0000 0.0000 0.1267(12) 0.160(10) Uiso 0.5 3 d S . 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
P1 C16 1.794(4) . ?
P1 C22 1.798(4) . ?
P1 C15 1.812(3) . ?
P1 C28 1.817(4) . ?
O1 C1 1.224(5) . ?
O2 C2 1.236(4) . ?
N1 C2 1.384(5) . ?
N1 C1 1.407(5) . ?
N1 C6 1.466(5) . ?
C1 C5 1.443(6) . ?
C2 C3 1.454(5) . ?
C3 C4 1.409(5) . ?
C3 C15 1.412(5) 10_655 ?
C4 C5 1.405(5) . ?
C4 C4 1.422(8) 10_655 ?
C5 C14 1.396(5) . ?
C6 C7 1.578(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.499(10) . ?
C7 C10 1.518(10) . ?
C7 C10X 1.820(19) . ?
C7 H7 1.0000 . ?
C8 C9 1.528(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.505(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.527(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.41(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C10X C11X 1.52(2) . ?
C10X H10C 0.9900 . ?
C10X H10D 0.9900 . ?
C11X C12X 1.56(2) . ?
C11X H11C 0.9900 . ?
C11X H11D 0.9900 . ?
C12X C13X 1.41(3) . ?
C12X H12C 0.9900 . ?
C12X H12D 0.9900 . ?
C13X H13D 0.9800 . ?
C13X H13E 0.9800 . ?
C13X H13F 0.9800 . ?
C14 C15 1.389(6) . ?
C14 H14 0.9500 . ?
C15 C3 1.412(5) 10_655 ?
C16 C17 1.373(7) . ?
C16 C21 1.407(6) . ?
C17 C18 1.401(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.400(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.349(11) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(9) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.377(7) . ?
C22 C23 1.403(6) . ?
C23 C24 1.401(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.325(12) . ?
C24 H24 0.9500 . ?
C25 C26 1.391(12) . ?
C25 H25 0.9500 . ?
C26 C27 1.410(7) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.387(7) . ?
C28 C33 1.394(6) . ?
C29 C30 1.397(8) . ?
C29 H29 0.9500 . ?
C30 C31 1.374(10) . ?
C30 H30 0.9500 . ?
C31 C32 1.366(10) . ?
C31 H31 0.9500 . ?
C32 C33 1.393(8) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 P1 C22 115.2(2) . . ?
C16 P1 C15 113.82(19) . . ?
C22 P1 C15 110.82(17) . . ?
C16 P1 C28 104.5(2) . . ?
C22 P1 C28 106.51(19) . . ?
C15 P1 C28 104.94(18) . . ?
C2 N1 C1 124.1(3) . . ?
C2 N1 C6 118.6(3) . . ?
C1 N1 C6 117.3(3) . . ?
O1 C1 N1 119.5(4) . . ?
O1 C1 C5 124.3(3) . . ?
N1 C1 C5 116.2(3) . . ?
O2 C2 N1 121.0(3) . . ?
O2 C2 C3 120.4(3) . . ?
N1 C2 C3 118.7(3) . . ?
C4 C3 C15 119.9(3) . 10_655 ?
C4 C3 C2 118.6(3) . . ?
C15 C3 C2 121.5(3) 10_655 . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 C4 119.6(4) . 10_655 ?
C3 C4 C4 119.7(4) . 10_655 ?
C14 C5 C4 119.8(4) . . ?
C14 C5 C1 118.9(3) . . ?
C4 C5 C1 121.3(3) . . ?
N1 C6 C7 110.4(4) . . ?
N1 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
N1 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C10 111.9(7) . . ?
C8 C7 C6 113.4(5) . . ?
C10 C7 C6 110.0(6) . . ?
C8 C7 C10X 104.6(9) . . ?
C6 C7 C10X 92.0(7) . . ?
C8 C7 H7 107.0 . . ?
C10 C7 H7 107.0 . . ?
C6 C7 H7 107.0 . . ?
C7 C8 C9 111.0(7) . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 115.9(8) . . ?
C11 C10 H10A 108.3 . . ?
C7 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C7 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C10 C11 C12 113.7(11) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 112.1(14) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11X C10X C7 99.6(14) . . ?
C11X C10X H10C 111.8 . . ?
C7 C10X H10C 111.8 . . ?
C11X C10X H10D 111.8 . . ?
C7 C10X H10D 111.8 . . ?
H10C C10X H10D 109.6 . . ?
C10X C11X C12X 107.0(17) . . ?
C10X C11X H11C 110.3 . . ?
C12X C11X H11C 110.3 . . ?
C10X C11X H11D 110.3 . . ?
C12X C11X H11D 110.3 . . ?
H11C C11X H11D 108.6 . . ?
C13X C12X C11X 104(2) . . ?
C13X C12X H12C 110.9 . . ?
C11X C12X H12C 110.9 . . ?
C13X C12X H12D 110.9 . . ?
C11X C12X H12D 110.9 . . ?
H12C C12X H12D 108.9 . . ?
C12X C13X H13D 109.5 . . ?
C12X C13X H13E 109.5 . . ?
H13D C13X H13E 109.5 . . ?
C12X C13X H13F 109.5 . . ?
H13D C13X H13F 109.5 . . ?
H13E C13X H13F 109.5 . . ?
C15 C14 C5 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C5 C14 H14 119.3 . . ?
C14 C15 C3 119.6(3) . 10_655 ?
C14 C15 P1 117.2(3) . . ?
C3 C15 P1 123.1(3) 10_655 . ?
C17 C16 C21 120.4(5) . . ?
C17 C16 P1 121.7(3) . . ?
C21 C16 P1 117.5(4) . . ?
C16 C17 C18 119.7(5) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 119.4(6) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C18 120.0(5) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 121.8(6) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C16 118.6(6) . . ?
C20 C21 H21 120.7 . . ?
C16 C21 H21 120.7 . . ?
C27 C22 C23 121.8(4) . . ?
C27 C22 P1 118.2(3) . . ?
C23 C22 P1 120.0(4) . . ?
C24 C23 C22 117.5(6) . . ?
C24 C23 H23 121.2 . . ?
C22 C23 H23 121.2 . . ?
C25 C24 C23 121.2(6) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 122.2(5) . . ?
C24 C25 H25 118.9 . . ?
C26 C25 H25 118.9 . . ?
C25 C26 C27 118.6(6) . . ?
C25 C26 H26 120.7 . . ?
C27 C26 H26 120.7 . . ?
C22 C27 C26 118.7(6) . . ?
C22 C27 H27 120.7 . . ?
C26 C27 H27 120.7 . . ?
C29 C28 C33 120.1(4) . . ?
C29 C28 P1 120.6(3) . . ?
C33 C28 P1 119.0(4) . . ?
C28 C29 C30 119.0(5) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C31 C30 C29 120.8(6) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C32 C31 C30 119.9(5) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C33 120.8(5) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C32 C33 C28 119.2(5) . . ?
C32 C33 H33 120.4 . . ?
C28 C33 H33 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 177.7(4) . . . . ?
C6 N1 C1 O1 -1.3(6) . . . . ?
C2 N1 C1 C5 -2.8(5) . . . . ?
C6 N1 C1 C5 178.1(3) . . . . ?
C1 N1 C2 O2 -174.0(3) . . . . ?
C6 N1 C2 O2 5.0(5) . . . . ?
C1 N1 C2 C3 6.5(5) . . . . ?
C6 N1 C2 C3 -174.4(3) . . . . ?
O2 C2 C3 C4 174.5(3) . . . . ?
N1 C2 C3 C4 -6.0(5) . . . . ?
O2 C2 C3 C15 -5.8(5) . . . 10_655 ?
N1 C2 C3 C15 173.6(3) . . . 10_655 ?
C15 C3 C4 C5 -177.5(3) 10_655 . . . ?
C2 C3 C4 C5 2.1(5) . . . . ?
C15 C3 C4 C4 1.9(6) 10_655 . . 10_655 ?
C2 C3 C4 C4 -178.4(4) . . . 10_655 ?
C3 C4 C5 C14 -177.9(3) . . . . ?
C4 C4 C5 C14 2.6(6) 10_655 . . . ?
C3 C4 C5 C1 1.6(5) . . . . ?
C4 C4 C5 C1 -177.8(4) 10_655 . . . ?
O1 C1 C5 C14 -2.4(6) . . . . ?
N1 C1 C5 C14 178.1(3) . . . . ?
O1 C1 C5 C4 178.0(4) . . . . ?
N1 C1 C5 C4 -1.4(5) . . . . ?
C2 N1 C6 C7 101.5(4) . . . . ?
C1 N1 C6 C7 -79.4(5) . . . . ?
N1 C6 C7 C8 -57.4(7) . . . . ?
N1 C6 C7 C10 176.4(6) . . . . ?
N1 C6 C7 C10X -164.3(7) . . . . ?
C10 C7 C8 C9 -65.2(10) . . . . ?
C6 C7 C8 C9 169.7(7) . . . . ?
C10X C7 C8 C9 -91.5(10) . . . . ?
C8 C7 C10 C11 167.9(8) . . . . ?
C6 C7 C10 C11 -65.1(10) . . . . ?
C7 C10 C11 C12 -177.8(9) . . . . ?
C10 C11 C12 C13 166.0(12) . . . . ?
C8 C7 C10X C11X 143.1(13) . . . . ?
C6 C7 C10X C11X -102.1(14) . . . . ?
C7 C10X C11X C12X -166.2(15) . . . . ?
C10X C11X C12X C13X -144(2) . . . . ?
C4 C5 C14 C15 -2.2(6) . . . . ?
C1 C5 C14 C15 178.2(4) . . . . ?
C5 C14 C15 C3 -0.3(6) . . . 10_655 ?
C5 C14 C15 P1 177.0(3) . . . . ?
C16 P1 C15 C14 106.0(3) . . . . ?
C22 P1 C15 C14 -122.3(3) . . . . ?
C28 P1 C15 C14 -7.7(3) . . . . ?
C16 P1 C15 C3 -76.9(3) . . . 10_655 ?
C22 P1 C15 C3 54.9(4) . . . 10_655 ?
C28 P1 C15 C3 169.5(3) . . . 10_655 ?
C22 P1 C16 C17 -120.6(4) . . . . ?
C15 P1 C16 C17 9.0(4) . . . . ?
C28 P1 C16 C17 122.9(4) . . . . ?
C22 P1 C16 C21 66.9(4) . . . . ?
C15 P1 C16 C21 -163.5(3) . . . . ?
C28 P1 C16 C21 -49.6(4) . . . . ?
C21 C16 C17 C18 2.4(7) . . . . ?
P1 C16 C17 C18 -169.8(4) . . . . ?
C16 C17 C18 C19 -1.0(8) . . . . ?
C17 C18 C19 C20 -2.3(9) . . . . ?
C18 C19 C20 C21 4.2(9) . . . . ?
C19 C20 C21 C16 -2.7(8) . . . . ?
C17 C16 C21 C20 -0.7(7) . . . . ?
P1 C16 C21 C20 171.9(4) . . . . ?
C16 P1 C22 C27 162.8(4) . . . . ?
C15 P1 C22 C27 31.7(4) . . . . ?
C28 P1 C22 C27 -81.9(4) . . . . ?
C16 P1 C22 C23 -18.6(4) . . . . ?
C15 P1 C22 C23 -149.6(4) . . . . ?
C28 P1 C22 C23 96.8(4) . . . . ?
C27 C22 C23 C24 -0.5(7) . . . . ?
P1 C22 C23 C24 -179.1(4) . . . . ?
C22 C23 C24 C25 1.1(9) . . . . ?
C23 C24 C25 C26 -1.1(11) . . . . ?
C24 C25 C26 C27 0.4(11) . . . . ?
C23 C22 C27 C26 -0.1(8) . . . . ?
P1 C22 C27 C26 178.5(5) . . . . ?
C25 C26 C27 C22 0.2(9) . . . . ?
C16 P1 C28 C29 146.8(3) . . . . ?
C22 P1 C28 C29 24.4(4) . . . . ?
C15 P1 C28 C29 -93.2(3) . . . . ?
C16 P1 C28 C33 -39.7(4) . . . . ?
C22 P1 C28 C33 -162.1(3) . . . . ?
C15 P1 C28 C33 80.3(3) . . . . ?
C33 C28 C29 C30 -0.1(6) . . . . ?
P1 C28 C29 C30 173.3(4) . . . . ?
C28 C29 C30 C31 -1.4(8) . . . . ?
C29 C30 C31 C32 2.3(8) . . . . ?
C30 C31 C32 C33 -1.7(8) . . . . ?
C31 C32 C33 C28 0.2(7) . . . . ?
C29 C28 C33 C32 0.7(6) . . . . ?
P1 C28 C33 C32 -172.8(3) . . . . ?

_refine_diff_density_max         1.495
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.200

####################################################################### 
# 
# 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_i121
_database_code_depnum_ccdc_archive 'CCDC 1871423'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C74 H86 F12 N2 O6 P4'
_chemical_formula_weight         1451.32

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

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

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

_cell_length_a                   15.5817(5)
_cell_length_b                   20.6208(6)
_cell_length_c                   22.0566(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7086.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9704
_cell_measurement_theta_min      4.73
_cell_measurement_theta_max      70.10

_exptl_crystal_description       'Rectangular Plate'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             3040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    1.714
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            76842
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.008
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_full        66.587
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6224
_reflns_number_gt                5881
_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_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1653P)²+20.3835P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00124(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6224
_refine_ls_number_parameters     600
_refine_ls_number_restraints     489
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.1029
_refine_ls_wR_factor_ref         0.2756
_refine_ls_wR_factor_gt          0.2711
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.164
_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
F1 F 0.4760(4) 0.4608(4) 0.7141(3) 0.088(3) Uani 0.623(12) 1 d D U P A 1
F2 F 0.3557(5) 0.5174(3) 0.6987(2) 0.090(3) Uani 0.623(12) 1 d D U P A 1
F3 F 0.3327(4) 0.4627(4) 0.6115(3) 0.109(5) Uani 0.623(12) 1 d D U P A 1
F4 F 0.4537(4) 0.4076(3) 0.6256(2) 0.086(3) Uani 0.623(12) 1 d D U P A 1
F5 F 0.3501(5) 0.4088(3) 0.6988(3) 0.060(2) Uani 0.623(12) 1 d D U P A 1
F6 F 0.4566(5) 0.5170(3) 0.6275(2) 0.076(3) Uani 0.623(12) 1 d D U P A 1
F1X F 0.4613(11) 0.4395(10) 0.7205(6) 0.125(7) Uani 0.377(12) 1 d D U P A 2
F2X F 0.3830(10) 0.5273(4) 0.6879(9) 0.111(6) Uani 0.377(12) 1 d D U P A 2
F3X F 0.3409(6) 0.4694(5) 0.6083(4) 0.039(3) Uani 0.377(12) 1 d D U P A 2
F4X F 0.4182(13) 0.3845(5) 0.6420(10) 0.157(8) Uani 0.377(12) 1 d D U P A 2
F5X F 0.3245(7) 0.4281(7) 0.6989(6) 0.062(4) Uani 0.377(12) 1 d D U P A 2
F6X F 0.4891(5) 0.4713(7) 0.6269(4) 0.064(3) Uani 0.377(12) 1 d D U P A 2
P1 P 0.37139(6) 0.68579(4) 0.49173(5) 0.0285(3) Uani 1 1 d . . . . .
P2 P 0.40471(9) 0.45830(8) 0.66329(5) 0.0610(5) Uani 1 1 d D . . . .
O1 O 0.70019(17) 0.63089(12) 0.53207(15) 0.0382(7) Uani 1 1 d . . . . .
O2 O 0.74358(17) 0.41629(12) 0.50044(12) 0.0278(6) Uani 1 1 d . . . . .
N1 N 0.72265(18) 0.52260(14) 0.52213(13) 0.0224(6) Uani 1 1 d . . . . .
C1 C 0.4554(2) 0.49597(16) 0.49583(14) 0.0203(7) Uani 1 1 d . . . . .
C2 C 0.4004(2) 0.55016(16) 0.49560(15) 0.0213(7) Uani 1 1 d . . . . .
C3 C 0.4345(2) 0.61206(16) 0.50079(15) 0.0234(7) Uani 1 1 d . . . . .
C4 C 0.5238(2) 0.61951(17) 0.50980(17) 0.0269(8) Uani 1 1 d . . . . .
H4 H 0.5471 0.6618 0.5140 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5773(2) 0.56690(17) 0.51255(15) 0.0224(7) Uani 1 1 d . . . . .
C6 C 0.6707(2) 0.57756(17) 0.52295(17) 0.0260(8) Uani 1 1 d . . . . .
C7 C 0.6932(2) 0.46065(16) 0.50846(15) 0.0216(7) Uani 1 1 d . . . . .
C8 C 0.3134(3) 0.7036(2) 0.5603(2) 0.0410(10) Uani 1 1 d . . . . .
C9 C 0.3089(3) 0.6582(3) 0.6068(2) 0.0474(11) Uani 1 1 d . . . . .
H9 H 0.3350 0.6170 0.6019 0.057 Uiso 1 1 calc R U . . .
C10 C 0.2665(4) 0.6728(4) 0.6604(3) 0.0695(17) Uani 1 1 d . . . . .
H10 H 0.2635 0.6415 0.6919 0.083 Uiso 1 1 calc R U . . .
C11 C 0.2293(5) 0.7318(5) 0.6677(4) 0.092(3) Uani 1 1 d . . . . .
H11 H 0.1999 0.7414 0.7044 0.111 Uiso 1 1 calc R U . . .
C12 C 0.2339(4) 0.7779(4) 0.6227(4) 0.084(3) Uani 1 1 d . . . . .
H12 H 0.2077 0.8190 0.6286 0.101 Uiso 1 1 calc R U . . .
C13 C 0.2766(3) 0.7650(3) 0.5683(3) 0.0606(16) Uani 1 1 d . . . . .
H13 H 0.2806 0.7971 0.5376 0.073 Uiso 1 1 calc R U . . .
C14 C 0.3096(2) 0.68069(17) 0.42305(19) 0.0299(8) Uani 1 1 d . . . . .
C15 C 0.2379(3) 0.71987(19) 0.4152(2) 0.0380(10) Uani 1 1 d . . . . .
H15 H 0.2210 0.7493 0.4461 0.046 Uiso 1 1 calc R U . . .
C16 C 0.1913(3) 0.7157(2) 0.3619(3) 0.0516(13) Uani 1 1 d . . . . .
H16 H 0.1427 0.7428 0.3561 0.062 Uiso 1 1 calc R U . . .
C17 C 0.2153(3) 0.6719(3) 0.3167(2) 0.0515(13) Uani 1 1 d . . . . .
H17 H 0.1820 0.6686 0.2807 0.062 Uiso 1 1 calc R U . . .
C18 C 0.2864(3) 0.6338(2) 0.3240(2) 0.0473(11) Uani 1 1 d . . . . .
H18 H 0.3023 0.6041 0.2930 0.057 Uiso 1 1 calc R U . . .
C19 C 0.3358(3) 0.63827(19) 0.37689(19) 0.0360(9) Uani 1 1 d . . . . .
H19 H 0.3863 0.6129 0.3815 0.043 Uiso 1 1 calc R U . . .
C20 C 0.4479(3) 0.74989(19) 0.4804(2) 0.0425(11) Uani 1 1 d . . . . .
C21 C 0.4776(3) 0.7626(2) 0.4221(3) 0.0581(14) Uani 1 1 d . . . . .
H21 H 0.4543 0.7394 0.3886 0.070 Uiso 1 1 calc R U . . .
C22 C 0.5413(4) 0.8092(3) 0.4123(4) 0.085(2) Uani 1 1 d . . . . .
H22 H 0.5607 0.8184 0.3724 0.102 Uiso 1 1 calc R U . . .
C23 C 0.5757(4) 0.8415(3) 0.4610(6) 0.098(3) Uani 1 1 d . . . . .
H23 H 0.6199 0.8724 0.4547 0.118 Uiso 1 1 calc R U . . .
C24 C 0.5468(5) 0.8296(3) 0.5190(5) 0.093(3) Uani 1 1 d . . . . .
H24 H 0.5712 0.8528 0.5520 0.111 Uiso 1 1 calc R U . . .
C25 C 0.4821(4) 0.7840(2) 0.5300(3) 0.0657(18) Uani 1 1 d . . . . .
H25 H 0.4618 0.7763 0.5699 0.079 Uiso 1 1 calc R U . . .
C26 C 0.8168(2) 0.53045(18) 0.53027(18) 0.0287(8) Uani 1 1 d . . . . .
H26A H 0.8309 0.5773 0.5299 0.034 Uiso 1 1 calc R U . . .
H26B H 0.8466 0.5100 0.4956 0.034 Uiso 1 1 calc R U . . .
C27 C 0.8503(3) 0.5009(2) 0.5886(2) 0.0454(11) Uani 1 1 d D . . . .
H27 H 0.8325 0.4543 0.5902 0.054 Uiso 1 1 calc R U . B 1
C28 C 0.9493(5) 0.5044(9) 0.5909(6) 0.0789(15) Uani 0.572(9) 1 d D U P C 1
H28A H 0.9729 0.4909 0.5512 0.095 Uiso 0.572(9) 1 calc R U P C 1
H28B H 0.9670 0.5499 0.5982 0.095 Uiso 0.572(9) 1 calc R U P C 1
C29 C 0.9863(5) 0.4618(7) 0.6401(7) 0.0795(15) Uani 0.572(9) 1 d D U P C 1
H29A H 0.9581 0.4188 0.6378 0.095 Uiso 0.572(9) 1 calc R U P C 1
H29B H 0.9715 0.4810 0.6799 0.095 Uiso 0.572(9) 1 calc R U P C 1
C30 C 1.0833(6) 0.4517(5) 0.6375(7) 0.0800(15) Uani 0.572(9) 1 d D U P C 1
H30A H 1.1003 0.4222 0.6709 0.096 Uiso 0.572(9) 1 calc R U P C 1
H30B H 1.0980 0.4301 0.5988 0.096 Uiso 0.572(9) 1 calc R U P C 1
C31 C 1.1349(6) 0.5136(6) 0.6426(6) 0.0805(15) Uani 0.572(9) 1 d D U P C 1
H31A H 1.1963 0.5033 0.6407 0.121 Uiso 0.572(9) 1 calc R U P C 1
H31B H 1.1198 0.5427 0.6092 0.121 Uiso 0.572(9) 1 calc R U P C 1
H31C H 1.1221 0.5348 0.6813 0.121 Uiso 0.572(9) 1 calc R U P C 1
C32 C 0.8073(10) 0.5375(9) 0.6422(7) 0.054(2) Uani 0.572(9) 1 d D U P C 1
H32A H 0.7443 0.5371 0.6365 0.065 Uiso 0.572(9) 1 calc R U P C 1
H32B H 0.8203 0.5145 0.6804 0.065 Uiso 0.572(9) 1 calc R U P C 1
C33 C 0.8382(10) 0.6081(8) 0.6473(5) 0.055(2) Uani 0.572(9) 1 d D U P C 1
H33A H 0.8095 0.6292 0.6815 0.082 Uiso 0.572(9) 1 calc R U P C 1
H33B H 0.9004 0.6087 0.6537 0.082 Uiso 0.572(9) 1 calc R U P C 1
H33C H 0.8244 0.6314 0.6098 0.082 Uiso 0.572(9) 1 calc R U P C 1
C28X C 0.9488(5) 0.4988(15) 0.5850(7) 0.0790(15) Uani 0.428(9) 1 d D U P C 2
H28C H 0.9656 0.4663 0.5541 0.095 Uiso 0.428(9) 1 calc R U P C 2
H28D H 0.9697 0.5416 0.5710 0.095 Uiso 0.428(9) 1 calc R U P C 2
C29X C 0.9932(6) 0.4823(10) 0.6439(7) 0.0795(15) Uani 0.428(9) 1 d D U P C 2
H29C H 0.9760 0.4380 0.6562 0.095 Uiso 0.428(9) 1 calc R U P C 2
H29D H 0.9728 0.5126 0.6756 0.095 Uiso 0.428(9) 1 calc R U P C 2
C30X C 1.0910(7) 0.4854(10) 0.6412(8) 0.0801(15) Uani 0.428(9) 1 d D U P C 2
H30C H 1.1097 0.4704 0.6007 0.096 Uiso 0.428(9) 1 calc R U P C 2
H30D H 1.1087 0.5313 0.6454 0.096 Uiso 0.428(9) 1 calc R U P C 2
C31X C 1.1376(8) 0.4462(9) 0.6885(7) 0.0804(15) Uani 0.428(9) 1 d D U P C 2
H31D H 1.1987 0.4574 0.6880 0.121 Uiso 0.428(9) 1 calc R U P C 2
H31E H 1.1308 0.3999 0.6796 0.121 Uiso 0.428(9) 1 calc R U P C 2
H31F H 1.1136 0.4557 0.7286 0.121 Uiso 0.428(9) 1 calc R U P C 2
C32X C 0.8144(14) 0.5303(13) 0.6475(9) 0.054(2) Uani 0.428(9) 1 d D U P C 2
H32C H 0.7510 0.5314 0.6446 0.065 Uiso 0.428(9) 1 calc R U P C 2
H32D H 0.8296 0.5013 0.6816 0.065 Uiso 0.428(9) 1 calc R U P C 2
C33X C 0.8463(13) 0.5990(11) 0.6626(6) 0.055(2) Uani 0.428(9) 1 d D U P C 2
H33D H 0.8202 0.6136 0.7006 0.082 Uiso 0.428(9) 1 calc R U P C 2
H33E H 0.9089 0.5986 0.6669 0.082 Uiso 0.428(9) 1 calc R U P C 2
H33F H 0.8301 0.6287 0.6298 0.082 Uiso 0.428(9) 1 calc R U P C 2
O3 O 0.5466(7) 0.7054(6) 0.7301(6) 0.0887(15) Uani 0.611(12) 1 d D U P D 1
C34 C 0.5931(9) 0.6054(8) 0.6989(9) 0.0899(18) Uani 0.611(12) 1 d D U P D 1
H34A H 0.5751 0.5623 0.6851 0.135 Uiso 0.611(12) 1 calc R U P D 1
H34B H 0.6281 0.6261 0.6674 0.135 Uiso 0.611(12) 1 calc R U P D 1
H34C H 0.6269 0.6012 0.7361 0.135 Uiso 0.611(12) 1 calc R U P D 1
C35 C 0.5199(10) 0.6438(8) 0.7104(9) 0.0887(16) Uani 0.611(12) 1 d D U P D 1
H35A H 0.4852 0.6480 0.6730 0.106 Uiso 0.611(12) 1 calc R U P D 1
H35B H 0.4840 0.6230 0.7419 0.106 Uiso 0.611(12) 1 calc R U P D 1
C36 C 0.4723(15) 0.7451(6) 0.7356(10) 0.0889(16) Uani 0.611(12) 1 d D U P D 1
H36A H 0.4416 0.7466 0.6963 0.107 Uiso 0.611(12) 1 calc R U P D 1
H36B H 0.4331 0.7264 0.7663 0.107 Uiso 0.611(12) 1 calc R U P D 1
C37 C 0.4955(8) 0.8083(5) 0.7530(8) 0.0884(18) Uani 0.611(12) 1 d D U P D 1
H37A H 0.4438 0.8351 0.7566 0.133 Uiso 0.611(12) 1 calc R U P D 1
H37B H 0.5252 0.8068 0.7921 0.133 Uiso 0.611(12) 1 calc R U P D 1
H37C H 0.5337 0.8270 0.7223 0.133 Uiso 0.611(12) 1 calc R U P D 1
O3X O 0.5291(12) 0.7059(9) 0.7137(10) 0.0890(16) Uani 0.389(12) 1 d D U P D 2
C34X C 0.6116(15) 0.6074(13) 0.6874(15) 0.0891(18) Uani 0.389(12) 1 d D U P D 2
H34D H 0.5993 0.5619 0.6781 0.134 Uiso 0.389(12) 1 calc R U P D 2
H34E H 0.6408 0.6275 0.6529 0.134 Uiso 0.389(12) 1 calc R U P D 2
H34F H 0.6486 0.6098 0.7233 0.134 Uiso 0.389(12) 1 calc R U P D 2
C35X C 0.5344(16) 0.6403(13) 0.6990(16) 0.0890(16) Uani 0.389(12) 1 d D U P D 2
H35C H 0.4981 0.6342 0.6626 0.107 Uiso 0.389(12) 1 calc R U P D 2
H35D H 0.5058 0.6166 0.7323 0.107 Uiso 0.389(12) 1 calc R U P D 2
C36X C 0.473(3) 0.7487(11) 0.7429(14) 0.0889(16) Uani 0.389(12) 1 d D U P D 2
H36C H 0.4987 0.7627 0.7817 0.107 Uiso 0.389(12) 1 calc R U P D 2
H36D H 0.4188 0.7254 0.7524 0.107 Uiso 0.389(12) 1 calc R U P D 2
C37X C 0.4530(13) 0.8038(9) 0.7084(12) 0.0890(18) Uani 0.389(12) 1 d D U P D 2
H37D H 0.4135 0.8316 0.7312 0.133 Uiso 0.389(12) 1 calc R U P D 2
H37E H 0.5058 0.8278 0.6995 0.133 Uiso 0.389(12) 1 calc R U P D 2
H37F H 0.4259 0.7905 0.6703 0.133 Uiso 0.389(12) 1 calc R U P D 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 P2 1.578(4) . ?
F2 P2 1.637(5) . ?
F3 P2 1.603(5) . ?
F4 P2 1.538(4) . ?
F5 P2 1.542(5) . ?
F6 P2 1.656(4) . ?
F1X P2 1.587(8) . ?
F2X P2 1.559(8) . ?
F3X P2 1.585(6) . ?
F4X P2 1.607(8) . ?
F5X P2 1.602(7) . ?
F6X P2 1.564(6) . ?
P1 C14 1.798(4) . ?
P1 C20 1.798(4) . ?
P1 C8 1.799(5) . ?
P1 C3 1.821(4) . ?
O1 C6 1.209(4) . ?
O2 C7 1.219(4) . ?
N1 C7 1.391(4) . ?
N1 C6 1.393(5) . ?
N1 C26 1.487(5) . ?
C1 C5 1.405(5) 5_666 ?
C1 C2 1.408(5) . ?
C1 C1 1.411(7) 5_666 ?
C2 C3 1.387(5) . ?
C2 C7 1.478(5) 5_666 ?
C3 C4 1.415(5) . ?
C4 C5 1.370(5) . ?
C4 H4 0.9500 . ?
C5 C1 1.405(5) 5_666 ?
C5 C6 1.490(5) . ?
C7 C2 1.479(5) 5_666 ?
C8 C9 1.390(7) . ?
C8 C13 1.401(6) . ?
C9 C10 1.386(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.357(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(12) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(10) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.390(6) . ?
C14 C19 1.403(6) . ?
C15 C16 1.384(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.396(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.368(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.401(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.391(8) . ?
C20 C25 1.405(7) . ?
C21 C22 1.399(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.373(13) . ?
C22 H22 0.9500 . ?
C23 C24 1.377(13) . ?
C23 H23 0.9500 . ?
C24 C25 1.401(10) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.516(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28X 1.539(8) . ?
C27 C32X 1.539(8) . ?
C27 C28 1.546(7) . ?
C27 C32 1.553(7) . ?
C27 H27 1.0000 . ?
C28 C29 1.509(7) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.528(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.512(8) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.537(7) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C28X C29X 1.510(8) . ?
C28X H28C 0.9900 . ?
C28X H28D 0.9900 . ?
C29X C30X 1.527(8) . ?
C29X H29C 0.9900 . ?
C29X H29D 0.9900 . ?
C30X C31X 1.506(9) . ?
C30X H30C 0.9900 . ?
C30X H30D 0.9900 . ?
C31X H31D 0.9800 . ?
C31X H31E 0.9800 . ?
C31X H31F 0.9800 . ?
C32X C33X 1.538(8) . ?
C32X H32C 0.9900 . ?
C32X H32D 0.9900 . ?
C33X H33D 0.9800 . ?
C33X H33E 0.9800 . ?
C33X H33F 0.9800 . ?
O3 C35 1.405(19) . ?
O3 C36 1.425(19) . ?
C34 C35 1.410(11) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.405(12) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
O3X C35X 1.39(3) . ?
O3X C36X 1.40(3) . ?
C34X C35X 1.406(12) . ?
C34X H34D 0.9800 . ?
C34X H34E 0.9800 . ?
C34X H34F 0.9800 . ?
C35X H35C 0.9900 . ?
C35X H35D 0.9900 . ?
C36X C37X 1.402(13) . ?
C36X H36C 0.9900 . ?
C36X H36D 0.9900 . ?
C37X H37D 0.9800 . ?
C37X H37E 0.9800 . ?
C37X H37F 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
C14 P1 C20 106.3(2) . . ?
C14 P1 C8 116.8(2) . . ?
C20 P1 C8 107.5(2) . . ?
C14 P1 C3 109.42(17) . . ?
C20 P1 C3 105.72(18) . . ?
C8 P1 C3 110.41(19) . . ?
F4 P2 F5 95.6(3) . . ?
F2X P2 F6X 101.8(7) . . ?
F4 P2 F1 93.2(3) . . ?
F5 P2 F1 92.9(3) . . ?
F2X P2 F3X 89.9(8) . . ?
F6X P2 F3X 96.3(5) . . ?
F2X P2 F1X 93.9(10) . . ?
F6X P2 F1X 89.0(8) . . ?
F3X P2 F1X 172.7(9) . . ?
F2X P2 F5X 90.9(7) . . ?
F6X P2 F5X 166.9(6) . . ?
F3X P2 F5X 86.7(6) . . ?
F1X P2 F5X 87.0(8) . . ?
F4 P2 F3 90.1(3) . . ?
F5 P2 F3 90.7(3) . . ?
F1 P2 F3 174.9(4) . . ?
F2X P2 F4X 173.8(9) . . ?
F6X P2 F4X 84.4(8) . . ?
F3X P2 F4X 89.7(8) . . ?
F1X P2 F4X 85.9(10) . . ?
F5X P2 F4X 82.9(8) . . ?
F4 P2 F2 174.5(3) . . ?
F5 P2 F2 89.7(3) . . ?
F1 P2 F2 88.0(3) . . ?
F3 P2 F2 88.3(3) . . ?
F4 P2 F6 89.8(3) . . ?
F5 P2 F6 174.4(3) . . ?
F1 P2 F6 88.3(3) . . ?
F3 P2 F6 87.8(3) . . ?
F2 P2 F6 84.9(3) . . ?
C7 N1 C6 124.0(3) . . ?
C7 N1 C26 116.9(3) . . ?
C6 N1 C26 118.9(3) . . ?
C5 C1 C2 120.7(3) 5_666 . ?
C5 C1 C1 118.9(4) 5_666 5_666 ?
C2 C1 C1 120.4(4) . 5_666 ?
C3 C2 C1 119.9(3) . . ?
C3 C2 C7 121.4(3) . 5_666 ?
C1 C2 C7 118.7(3) . 5_666 ?
C2 C3 C4 119.2(3) . . ?
C2 C3 P1 123.6(3) . . ?
C4 C3 P1 117.1(3) . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C1 120.3(3) . 5_666 ?
C4 C5 C6 119.0(3) . . ?
C1 C5 C6 120.7(3) 5_666 . ?
O1 C6 N1 121.4(3) . . ?
O1 C6 C5 122.1(3) . . ?
N1 C6 C5 116.5(3) . . ?
O2 C7 N1 120.6(3) . . ?
O2 C7 C2 120.9(3) . 5_666 ?
N1 C7 C2 118.5(3) . 5_666 ?
C9 C8 C13 119.5(5) . . ?
C9 C8 P1 120.6(3) . . ?
C13 C8 P1 119.7(4) . . ?
C10 C9 C8 120.5(5) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 119.9(7) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.7(7) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 120.9(6) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 118.4(7) . . ?
C12 C13 H13 120.8 . . ?
C8 C13 H13 120.8 . . ?
C15 C14 C19 120.4(4) . . ?
C15 C14 P1 120.1(3) . . ?
C19 C14 P1 119.5(3) . . ?
C16 C15 C14 119.5(4) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.4(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.3(5) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 119.1(4) . . ?
C18 C19 H19 120.5 . . ?
C14 C19 H19 120.5 . . ?
C21 C20 C25 120.0(5) . . ?
C21 C20 P1 119.2(4) . . ?
C25 C20 P1 120.7(5) . . ?
C20 C21 C22 120.5(6) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.3(8) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.9(6) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C23 C24 C25 121.0(7) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C20 118.3(7) . . ?
C24 C25 H25 120.8 . . ?
C20 C25 H25 120.8 . . ?
N1 C26 C27 113.5(3) . . ?
N1 C26 H26A 108.9 . . ?
C27 C26 H26A 108.9 . . ?
N1 C26 H26B 108.9 . . ?
C27 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C26 C27 C28X 108.1(7) . . ?
C26 C27 C32X 115.7(12) . . ?
C28X C27 C32X 114.6(8) . . ?
C26 C27 C28 110.7(6) . . ?
C26 C27 C32 107.6(9) . . ?
C28 C27 C32 112.5(6) . . ?
C26 C27 H27 108.7 . . ?
C28 C27 H27 108.7 . . ?
C32 C27 H27 108.7 . . ?
C29 C28 C27 112.2(9) . . ?
C29 C28 H28A 109.2 . . ?
C27 C28 H28A 109.2 . . ?
C29 C28 H28B 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C28 C29 C30 115.5(6) . . ?
C28 C29 H29A 108.4 . . ?
C30 C29 H29A 108.4 . . ?
C28 C29 H29B 108.4 . . ?
C30 C29 H29B 108.4 . . ?
H29A C29 H29B 107.5 . . ?
C31 C30 C29 114.2(7) . . ?
C31 C30 H30A 108.7 . . ?
C29 C30 H30A 108.7 . . ?
C31 C30 H30B 108.7 . . ?
C29 C30 H30B 108.7 . . ?
H30A C30 H30B 107.6 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C27 112.4(11) . . ?
C33 C32 H32A 109.1 . . ?
C27 C32 H32A 109.1 . . ?
C33 C32 H32B 109.1 . . ?
C27 C32 H32B 109.1 . . ?
H32A C32 H32B 107.9 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C29X C28X C27 114.8(9) . . ?
C29X C28X H28C 108.6 . . ?
C27 C28X H28C 108.6 . . ?
C29X C28X H28D 108.6 . . ?
C27 C28X H28D 108.6 . . ?
H28C C28X H28D 107.6 . . ?
C28X C29X C30X 114.5(7) . . ?
C28X C29X H29C 108.6 . . ?
C30X C29X H29C 108.6 . . ?
C28X C29X H29D 108.6 . . ?
C30X C29X H29D 108.6 . . ?
H29C C29X H29D 107.6 . . ?
C31X C30X C29X 115.6(8) . . ?
C31X C30X H30C 108.4 . . ?
C29X C30X H30C 108.4 . . ?
C31X C30X H30D 108.4 . . ?
C29X C30X H30D 108.4 . . ?
H30C C30X H30D 107.4 . . ?
C30X C31X H31D 109.5 . . ?
C30X C31X H31E 109.5 . . ?
H31D C31X H31E 109.5 . . ?
C30X C31X H31F 109.5 . . ?
H31D C31X H31F 109.5 . . ?
H31E C31X H31F 109.5 . . ?
C33X C32X C27 115.3(14) . . ?
C33X C32X H32C 108.4 . . ?
C27 C32X H32C 108.4 . . ?
C33X C32X H32D 108.4 . . ?
C27 C32X H32D 108.4 . . ?
H32C C32X H32D 107.5 . . ?
C32X C33X H33D 109.5 . . ?
C32X C33X H33E 109.5 . . ?
H33D C33X H33E 109.5 . . ?
C32X C33X H33F 109.5 . . ?
H33D C33X H33F 109.5 . . ?
H33E C33X H33F 109.5 . . ?
C35 O3 C36 107.8(15) . . ?
C35 C34 H34A 109.5 . . ?
C35 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C35 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O3 C35 C34 108.8(15) . . ?
O3 C35 H35A 109.9 . . ?
C34 C35 H35A 109.9 . . ?
O3 C35 H35B 109.9 . . ?
C34 C35 H35B 109.9 . . ?
H35A C35 H35B 108.3 . . ?
C37 C36 O3 110.4(19) . . ?
C37 C36 H36A 109.6 . . ?
O3 C36 H36A 109.6 . . ?
C37 C36 H36B 109.6 . . ?
O3 C36 H36B 109.6 . . ?
H36A C36 H36B 108.1 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35X O3X C36X 139(3) . . ?
C35X C34X H34D 109.5 . . ?
C35X C34X H34E 109.5 . . ?
H34D C34X H34E 109.5 . . ?
C35X C34X H34F 109.5 . . ?
H34D C34X H34F 109.5 . . ?
H34E C34X H34F 109.5 . . ?
O3X C35X C34X 124(3) . . ?
O3X C35X H35C 106.3 . . ?
C34X C35X H35C 106.3 . . ?
O3X C35X H35D 106.3 . . ?
C34X C35X H35D 106.3 . . ?
H35C C35X H35D 106.4 . . ?
O3X C36X C37X 113(3) . . ?
O3X C36X H36C 108.9 . . ?
C37X C36X H36C 108.9 . . ?
O3X C36X H36D 108.9 . . ?
C37X C36X H36D 108.9 . . ?
H36C C36X H36D 107.7 . . ?
C36X C37X H37D 109.5 . . ?
C36X C37X H37E 109.5 . . ?
H37D C37X H37E 109.5 . . ?
C36X C37X H37F 109.5 . . ?
H37D C37X H37F 109.5 . . ?
H37E C37X H37F 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
C5 C1 C2 C3 -176.7(3) 5_666 . . . ?
C1 C1 C2 C3 3.0(6) 5_666 . . . ?
C5 C1 C2 C7 5.1(5) 5_666 . . 5_666 ?
C1 C1 C2 C7 -175.3(4) 5_666 . . 5_666 ?
C1 C2 C3 C4 -3.7(5) . . . . ?
C7 C2 C3 C4 174.6(3) 5_666 . . . ?
C1 C2 C3 P1 172.2(3) . . . . ?
C7 C2 C3 P1 -9.6(5) 5_666 . . . ?
C14 P1 C3 C2 -49.4(4) . . . . ?
C20 P1 C3 C2 -163.5(3) . . . . ?
C8 P1 C3 C2 80.6(3) . . . . ?
C14 P1 C3 C4 126.6(3) . . . . ?
C20 P1 C3 C4 12.5(4) . . . . ?
C8 P1 C3 C4 -103.5(3) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
P1 C3 C4 C5 -175.1(3) . . . . ?
C3 C4 C5 C1 2.3(5) . . . 5_666 ?
C3 C4 C5 C6 -179.2(3) . . . . ?
C7 N1 C6 O1 -176.1(4) . . . . ?
C26 N1 C6 O1 -2.4(5) . . . . ?
C7 N1 C6 C5 4.3(5) . . . . ?
C26 N1 C6 C5 178.1(3) . . . . ?
C4 C5 C6 O1 3.8(6) . . . . ?
C1 C5 C6 O1 -177.8(4) 5_666 . . . ?
C4 C5 C6 N1 -176.7(3) . . . . ?
C1 C5 C6 N1 1.7(5) 5_666 . . . ?
C6 N1 C7 O2 170.0(3) . . . . ?
C26 N1 C7 O2 -3.9(5) . . . . ?
C6 N1 C7 C2 -10.5(5) . . . 5_666 ?
C26 N1 C7 C2 175.6(3) . . . 5_666 ?
C14 P1 C8 C9 115.1(4) . . . . ?
C20 P1 C8 C9 -125.6(4) . . . . ?
C3 P1 C8 C9 -10.8(4) . . . . ?
C14 P1 C8 C13 -68.5(4) . . . . ?
C20 P1 C8 C13 50.7(4) . . . . ?
C3 P1 C8 C13 165.6(3) . . . . ?
C13 C8 C9 C10 1.6(7) . . . . ?
P1 C8 C9 C10 177.9(4) . . . . ?
C8 C9 C10 C11 -0.3(8) . . . . ?
C9 C10 C11 C12 -0.6(10) . . . . ?
C10 C11 C12 C13 0.2(11) . . . . ?
C11 C12 C13 C8 1.1(9) . . . . ?
C9 C8 C13 C12 -2.0(7) . . . . ?
P1 C8 C13 C12 -178.4(4) . . . . ?
C20 P1 C14 C15 -86.4(4) . . . . ?
C8 P1 C14 C15 33.5(4) . . . . ?
C3 P1 C14 C15 159.8(3) . . . . ?
C20 P1 C14 C19 91.8(3) . . . . ?
C8 P1 C14 C19 -148.3(3) . . . . ?
C3 P1 C14 C19 -21.9(4) . . . . ?
C19 C14 C15 C16 1.4(6) . . . . ?
P1 C14 C15 C16 179.6(3) . . . . ?
C14 C15 C16 C17 0.9(7) . . . . ?
C15 C16 C17 C18 -1.6(7) . . . . ?
C16 C17 C18 C19 0.1(7) . . . . ?
C17 C18 C19 C14 2.2(6) . . . . ?
C15 C14 C19 C18 -2.9(6) . . . . ?
P1 C14 C19 C18 178.9(3) . . . . ?
C14 P1 C20 C21 -29.8(4) . . . . ?
C8 P1 C20 C21 -155.7(4) . . . . ?
C3 P1 C20 C21 86.4(4) . . . . ?
C14 P1 C20 C25 154.5(3) . . . . ?
C8 P1 C20 C25 28.7(4) . . . . ?
C3 P1 C20 C25 -89.3(4) . . . . ?
C25 C20 C21 C22 0.0(7) . . . . ?
P1 C20 C21 C22 -175.7(4) . . . . ?
C20 C21 C22 C23 1.2(9) . . . . ?
C21 C22 C23 C24 -1.5(10) . . . . ?
C22 C23 C24 C25 0.5(10) . . . . ?
C23 C24 C25 C20 0.8(8) . . . . ?
C21 C20 C25 C24 -1.0(7) . . . . ?
P1 C20 C25 C24 174.6(4) . . . . ?
C7 N1 C26 C27 -72.1(4) . . . . ?
C6 N1 C26 C27 113.7(4) . . . . ?
N1 C26 C27 C28X 167.7(12) . . . . ?
N1 C26 C27 C32X -62.2(10) . . . . ?
N1 C26 C27 C28 174.1(8) . . . . ?
N1 C26 C27 C32 -62.7(8) . . . . ?
C26 C27 C28 C29 -166.1(12) . . . . ?
C32 C27 C28 C29 73.5(18) . . . . ?
C27 C28 C29 C30 168.3(8) . . . . ?
C28 C29 C30 C31 60.0(17) . . . . ?
C26 C27 C32 C33 -68.3(11) . . . . ?
C28 C27 C32 C33 53.8(15) . . . . ?
C26 C27 C28X C29X 169.2(19) . . . . ?
C32X C27 C28X C29X 38(3) . . . . ?
C27 C28X C29X C30X -175.5(17) . . . . ?
C28X C29X C30X C31X -157(2) . . . . ?
C26 C27 C32X C33X -71.3(15) . . . . ?
C28X C27 C32X C33X 56(2) . . . . ?
C36 O3 C35 C34 174.3(15) . . . . ?
C35 O3 C36 C37 -177.7(15) . . . . ?
C36X O3X C35X C34X -157(3) . . . . ?
C35X O3X C36X C37X -128(3) . . . . ?

_refine_diff_density_max         1.353
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.155

####################################################################### 
# 
# 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_I080
_database_code_depnum_ccdc_archive 'CCDC 1871425'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H66 N2 O4 P2'
_chemical_formula_weight         1013.14

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'
P P 0.2955 0.4335 '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      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                   14.2234(9)
_cell_length_b                   15.5567(11)
_cell_length_c                   12.5242(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.744(2)
_cell_angle_gamma                90
_cell_volume                     2624.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      66.60

_exptl_crystal_description       Block
_exptl_crystal_colour            Dark_red
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             1076
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    1.166
_shelx_estimated_absorpt_T_min   0.785
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5701
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25696
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.342
_diffrn_reflns_theta_max         66.676
_diffrn_reflns_theta_full        66.676
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4621
_reflns_number_gt                4081
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1242P)²+2.6684P] 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         4621
_refine_ls_number_parameters     515
_refine_ls_number_restraints     695
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0711
_refine_ls_wR_factor_ref         0.2176
_refine_ls_wR_factor_gt          0.2076
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.77021(5) 0.62162(6) 0.70812(6) 0.0408(3) Uani 1 1 d . . . . .
N1 N 0.54106(17) 0.38949(17) 0.27741(18) 0.0346(6) Uani 1 1 d . . . . .
C1 C 0.4440(2) 0.3933(2) 0.2809(2) 0.0343(6) Uani 1 1 d . . . . .
O1 O 0.37450(14) 0.35954(15) 0.20456(15) 0.0386(5) Uani 1 1 d . . . . .
O2 O 0.70685(13) 0.42112(14) 0.34369(15) 0.0369(5) Uani 1 1 d . . . . .
C2 C 0.42820(19) 0.4363(2) 0.3740(2) 0.0321(6) Uani 1 1 d . . . . .
C4 C 0.60461(19) 0.47643(19) 0.4448(2) 0.0313(6) Uani 1 1 d . . . . .
C3 C 0.50758(19) 0.47740(19) 0.4536(2) 0.0303(6) Uani 1 1 d . . . . .
C5 C 0.62384(19) 0.4292(2) 0.3550(2) 0.0319(6) Uani 1 1 d . . . . .
C6 C 0.68352(19) 0.5191(2) 0.5245(2) 0.0334(6) Uani 1 1 d . . . . .
H6 H 0.7475 0.5182 0.5160 0.040 Uiso 1 1 calc R U . . .
C7 C 0.67035(19) 0.5622(2) 0.6147(2) 0.0342(6) Uani 1 1 d . . . . .
C8 C 0.5585(2) 0.3374(2) 0.1876(2) 0.0424(7) Uani 1 1 d D U . . .
H8A H 0.498(3) 0.340(2) 0.125(3) 0.051 Uiso 1 1 d . U . . .
H8B H 0.609(3) 0.364(2) 0.164(3) 0.051 Uiso 1 1 d . U . . .
C9 C 0.5770(9) 0.2406(4) 0.2181(11) 0.0551(19) Uani 0.5 1 d D U P A 1
H9 H 0.6399 0.2448 0.2832 0.066 Uiso 0.5 1 calc R U P A 1
C10 C 0.5144(11) 0.1875(8) 0.2715(15) 0.062(2) Uani 0.5 1 d D U P A 1
H10A H 0.4982 0.2251 0.3270 0.075 Uiso 0.5 1 calc R U P A 1
H10B H 0.4510 0.1752 0.2114 0.075 Uiso 0.5 1 calc R U P A 1
C11 C 0.5510(17) 0.1042(10) 0.330(2) 0.059(3) Uani 0.5 1 d D U P A 1
H11A H 0.5075 0.0861 0.3725 0.089 Uiso 0.5 1 calc R U P A 1
H11B H 0.6188 0.1116 0.3814 0.089 Uiso 0.5 1 calc R U P A 1
H11C H 0.5506 0.0602 0.2736 0.089 Uiso 0.5 1 calc R U P A 1
C12 C 0.6145(9) 0.1902(8) 0.1347(13) 0.056(2) Uani 0.5 1 d D U P A 1
H12A H 0.6446 0.1362 0.1722 0.067 Uiso 0.5 1 calc R U P A 1
H12B H 0.5560 0.1739 0.0700 0.067 Uiso 0.5 1 calc R U P A 1
C13 C 0.6891(6) 0.2326(7) 0.0877(9) 0.060(2) Uani 0.5 1 d D U P A 1
H13A H 0.6534 0.2426 0.0068 0.073 Uiso 0.5 1 calc R U P A 1
H13B H 0.7023 0.2901 0.1233 0.073 Uiso 0.5 1 calc R U P A 1
C14 C 0.7846(6) 0.1985(7) 0.0932(11) 0.091(2) Uani 0.5 1 d D U P A 1
H14A H 0.7744 0.1758 0.0164 0.109 Uiso 0.5 1 calc R U P A 1
H14B H 0.7925 0.1473 0.1422 0.109 Uiso 0.5 1 calc R U P A 1
C15 C 0.8837(7) 0.2366(9) 0.1261(14) 0.077(3) Uani 0.5 1 d D U P A 1
H15A H 0.9183 0.2173 0.0742 0.116 Uiso 0.5 1 calc R U P A 1
H15B H 0.9213 0.2188 0.2030 0.116 Uiso 0.5 1 calc R U P A 1
H15C H 0.8780 0.2994 0.1230 0.116 Uiso 0.5 1 calc R U P A 1
C9X C 0.5936(8) 0.2453(4) 0.2309(9) 0.0459(18) Uani 0.5 1 d D U P A 2
H9X H 0.6575 0.2464 0.2948 0.055 Uiso 0.5 1 calc R U P A 2
C10X C 0.5096(10) 0.2057(8) 0.2659(13) 0.058(2) Uani 0.5 1 d D U P A 2
H10C H 0.4923 0.2449 0.3190 0.070 Uiso 0.5 1 calc R U P A 2
H10D H 0.4501 0.1989 0.1985 0.070 Uiso 0.5 1 calc R U P A 2
C11X C 0.5386(16) 0.1209(10) 0.320(2) 0.055(3) Uani 0.5 1 d D U P A 2
H11E H 0.4806 0.0934 0.3317 0.082 Uiso 0.5 1 calc R U P A 2
H11F H 0.5905 0.1286 0.3932 0.082 Uiso 0.5 1 calc R U P A 2
H11G H 0.5639 0.0845 0.2717 0.082 Uiso 0.5 1 calc R U P A 2
C12X C 0.6061(9) 0.2036(9) 0.1246(13) 0.055(2) Uani 0.5 1 d D U P A 2
H12C H 0.5914 0.1414 0.1254 0.066 Uiso 0.5 1 calc R U P A 2
H12D H 0.5565 0.2289 0.0573 0.066 Uiso 0.5 1 calc R U P A 2
C13X C 0.7073(6) 0.2141(7) 0.1134(9) 0.0602(17) Uani 0.5 1 d D U P A 2
H13C H 0.7075 0.1744 0.0516 0.072 Uiso 0.5 1 calc R U P A 2
H13D H 0.7067 0.2727 0.0824 0.072 Uiso 0.5 1 calc R U P A 2
C14X C 0.7962(5) 0.2062(5) 0.1873(5) 0.0471(14) Uani 0.5 1 d D U P A 2
H14C H 0.7978 0.1510 0.2272 0.057 Uiso 0.5 1 calc R U P A 2
H14D H 0.8040 0.2524 0.2438 0.057 Uiso 0.5 1 calc R U P A 2
C15X C 0.8874(7) 0.2085(7) 0.1485(11) 0.055(2) Uani 0.5 1 d D U P A 2
H15E H 0.9354 0.1653 0.1900 0.082 Uiso 0.5 1 calc R U P A 2
H15F H 0.9179 0.2657 0.1630 0.082 Uiso 0.5 1 calc R U P A 2
H15G H 0.8676 0.1961 0.0676 0.082 Uiso 0.5 1 calc R U P A 2
C16 C 0.8789(11) 0.5941(7) 0.6657(11) 0.030(2) Uani 0.5 1 d . U P B 1
C17 C 0.9191(9) 0.5123(6) 0.6724(10) 0.0321(18) Uani 0.5 1 d . U P B 1
H17 H 0.8867 0.4650 0.6935 0.039 Uiso 0.5 1 calc R U P B 1
C18 C 1.0064(8) 0.4996(6) 0.6483(9) 0.0352(18) Uani 0.5 1 d . U P B 1
H18 H 1.0331 0.4433 0.6515 0.042 Uiso 0.5 1 calc R U P B 1
C19 C 1.0553(8) 0.5689(7) 0.6192(8) 0.0356(18) Uani 0.5 1 d . U P B 1
H19 H 1.1163 0.5600 0.6051 0.043 Uiso 0.5 1 calc R U P B 1
C20 C 1.0157(8) 0.6496(7) 0.6111(8) 0.0379(17) Uani 0.5 1 d . U P B 1
H20 H 1.0485 0.6967 0.5901 0.046 Uiso 0.5 1 calc R U P B 1
C21 C 0.9259(9) 0.6626(6) 0.6339(9) 0.0353(19) Uani 0.5 1 d . U P B 1
H21 H 0.8976 0.7185 0.6274 0.042 Uiso 0.5 1 calc R U P B 1
C16X C 0.8777(10) 0.6222(6) 0.6559(11) 0.028(2) Uani 0.5 1 d . U P B 2
C17X C 0.9239(10) 0.5422(6) 0.6660(10) 0.0328(19) Uani 0.5 1 d . U P B 2
H17X H 0.8955 0.4941 0.6909 0.039 Uiso 0.5 1 calc R U P B 2
C18X C 1.0118(9) 0.5322(6) 0.6398(9) 0.0345(19) Uani 0.5 1 d . U P B 2
H18X H 1.0431 0.4776 0.6463 0.041 Uiso 0.5 1 calc R U P B 2
C19X C 1.0526(8) 0.6033(7) 0.6041(8) 0.0361(19) Uani 0.5 1 d . U P B 2
H19X H 1.1138 0.5980 0.5892 0.043 Uiso 0.5 1 calc R U P B 2
C20X C 1.0050(7) 0.6810(6) 0.5902(8) 0.0366(17) Uani 0.5 1 d . U P B 2
H20X H 1.0318 0.7284 0.5620 0.044 Uiso 0.5 1 calc R U P B 2
C21X C 0.9183(8) 0.6917(6) 0.6166(8) 0.0307(17) Uani 0.5 1 d . U P B 2
H21X H 0.8868 0.7463 0.6079 0.037 Uiso 0.5 1 calc R U P B 2
C22 C 0.7468(2) 0.7346(2) 0.7017(2) 0.0413(8) Uani 1 1 d . . . . .
C23 C 0.7077(2) 0.7724(3) 0.5940(2) 0.0446(8) Uani 1 1 d . . . . .
H23 H 0.6906 0.7370 0.5287 0.054 Uiso 1 1 calc R U . . .
C24 C 0.6940(2) 0.8597(3) 0.5824(3) 0.0501(9) Uani 1 1 d . . . . .
H24 H 0.6685 0.8846 0.5095 0.060 Uiso 1 1 calc R U . . .
C25 C 0.7177(3) 0.9115(3) 0.6781(3) 0.0513(9) Uani 1 1 d . . . . .
H25 H 0.7090 0.9720 0.6703 0.062 Uiso 1 1 calc R U . . .
C26 C 0.7537(2) 0.8754(2) 0.7843(3) 0.0483(9) Uani 1 1 d . . . . .
H26 H 0.7682 0.9110 0.8491 0.058 Uiso 1 1 calc R U . . .
C27 C 0.7688(2) 0.7871(3) 0.7969(2) 0.0453(8) Uani 1 1 d . . . . .
H27 H 0.7941 0.7627 0.8701 0.054 Uiso 1 1 calc R U . . .
C28 C 0.8126(7) 0.5645(5) 0.8494(8) 0.0375(10) Uani 0.5 1 d . U P B 1
C29 C 0.7715(6) 0.4864(5) 0.8674(6) 0.0389(10) Uani 0.5 1 d . U P B 1
H29 H 0.7197 0.4608 0.8080 0.047 Uiso 0.5 1 calc R U P B 1
C30 C 0.8057(5) 0.4463(5) 0.9708(5) 0.0397(10) Uani 0.5 1 d . U P B 1
H30 H 0.7787 0.3927 0.9825 0.048 Uiso 0.5 1 calc R U P B 1
C31 C 0.8808(5) 0.4854(5) 1.0584(5) 0.0386(10) Uani 0.5 1 d . U P B 1
H31 H 0.9026 0.4587 1.1305 0.046 Uiso 0.5 1 calc R U P B 1
C32 C 0.9240(5) 0.5622(6) 1.0423(6) 0.0385(10) Uani 0.5 1 d . U P B 1
H32 H 0.9755 0.5879 1.1020 0.046 Uiso 0.5 1 calc R U P B 1
C33 C 0.8905(6) 0.6004(5) 0.9377(6) 0.0385(10) Uani 0.5 1 d . U P B 1
H33 H 0.9207 0.6521 0.9249 0.046 Uiso 0.5 1 calc R U P B 1
C28X C 0.8215(7) 0.5906(5) 0.8488(8) 0.0376(10) Uani 0.5 1 d . U P B 2
C29X C 0.9048(6) 0.6304(5) 0.9237(6) 0.0388(10) Uani 0.5 1 d . U P B 2
H29X H 0.9332 0.6795 0.9010 0.047 Uiso 0.5 1 calc R U P B 2
C30X C 0.9456(5) 0.5973(6) 1.0318(5) 0.0409(10) Uani 0.5 1 d . U P B 2
H30X H 1.0013 0.6245 1.0840 0.049 Uiso 0.5 1 calc R U P B 2
C31X C 0.9056(5) 0.5261(7) 1.0625(6) 0.0408(10) Uani 0.5 1 d . U P B 2
H31X H 0.9338 0.5045 1.1370 0.049 Uiso 0.5 1 calc R U P B 2
C32X C 0.8233(5) 0.4829(5) 0.9874(5) 0.0405(10) Uani 0.5 1 d . U P B 2
H32X H 0.7973 0.4322 1.0096 0.049 Uiso 0.5 1 calc R U P B 2
C33X C 0.7817(6) 0.5172(5) 0.8797(6) 0.0390(10) Uani 0.5 1 d . U P B 2
H33X H 0.7259 0.4902 0.8274 0.047 Uiso 0.5 1 calc R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C28X 1.745(9) . ?
P1 C7 1.781(3) . ?
P1 C22 1.786(4) . ?
P1 C16 1.839(15) . ?
P1 C16X 1.847(15) . ?
P1 C28 1.897(9) . ?
N1 C1 1.396(4) . ?
N1 C5 1.406(4) . ?
N1 C8 1.470(4) . ?
C1 O1 1.249(4) . ?
C1 C2 1.423(4) . ?
O2 C5 1.240(3) . ?
C2 C3 1.398(4) . ?
C2 C7 1.454(4) 3_666 ?
C4 C6 1.406(4) . ?
C4 C3 1.419(4) . ?
C4 C5 1.441(4) . ?
C3 C3 1.433(5) 3_666 ?
C6 C7 1.377(4) . ?
C6 H6 0.9500 . ?
C7 C2 1.454(4) 3_666 ?
C8 C9 1.555(6) . ?
C8 C9X 1.556(6) . ?
C8 H8A 0.96(4) . ?
C8 H8B 0.95(4) . ?
C9 C10 1.518(8) . ?
C9 C12 1.533(7) . ?
C9 H9 1.0000 . ?
C10 C11 1.497(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.519(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.438(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.462(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C9X C10X 1.527(10) . ?
C9X C12X 1.542(11) . ?
C9X H9X 1.0000 . ?
C10X C11X 1.482(12) . ?
C10X H10C 0.9900 . ?
C10X H10D 0.9900 . ?
C11X H11E 0.9800 . ?
C11X H11F 0.9800 . ?
C11X H11G 0.9800 . ?
C12X C13X 1.500(10) . ?
C12X H12C 0.9900 . ?
C12X H12D 0.9900 . ?
C13X C14X 1.311(11) . ?
C13X H13C 0.9900 . ?
C13X H13D 0.9900 . ?
C14X C15X 1.525(10) . ?
C14X H14C 0.9900 . ?
C14X H14D 0.9900 . ?
C15X H15E 0.9800 . ?
C15X H15F 0.9800 . ?
C15X H15G 0.9800 . ?
C16 C21 1.382(13) . ?
C16 C17 1.387(13) . ?
C17 C18 1.383(14) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(12) . ?
C18 H18 0.9500 . ?
C19 C20 1.366(13) . ?
C19 H19 0.9500 . ?
C20 C21 1.411(15) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C16X C21X 1.388(13) . ?
C16X C17X 1.393(12) . ?
C17X C18X 1.400(16) . ?
C17X H17X 0.9500 . ?
C18X C19X 1.388(13) . ?
C18X H18X 0.9500 . ?
C19X C20X 1.370(12) . ?
C19X H19X 0.9500 . ?
C20X C21X 1.385(13) . ?
C20X H20X 0.9500 . ?
C21X H21X 0.9500 . ?
C22 C27 1.396(4) . ?
C22 C23 1.412(5) . ?
C23 C24 1.374(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(6) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.397(11) . ?
C28 C33 1.405(10) . ?
C29 C30 1.378(10) . ?
C29 H29 0.9500 . ?
C30 C31 1.400(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.389(11) . ?
C31 H31 0.9500 . ?
C32 C33 1.376(11) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C28X C33X 1.384(11) . ?
C28X C29X 1.397(10) . ?
C29X C30X 1.388(9) . ?
C29X H29X 0.9500 . ?
C30X C31X 1.358(11) . ?
C30X H30X 0.9500 . ?
C31X C32X 1.413(11) . ?
C31X H31X 0.9500 . ?
C32X C33X 1.393(10) . ?
C32X H32X 0.9500 . ?
C33X H33X 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C28X P1 C7 120.4(3) . . ?
C28X P1 C22 109.2(3) . . ?
C7 P1 C22 112.54(13) . . ?
C7 P1 C16 104.9(4) . . ?
C22 P1 C16 112.2(3) . . ?
C28X P1 C16X 103.5(5) . . ?
C7 P1 C16X 110.2(4) . . ?
C22 P1 C16X 98.3(3) . . ?
C7 P1 C28 108.5(3) . . ?
C22 P1 C28 120.1(3) . . ?
C16 P1 C28 96.6(5) . . ?
C1 N1 C5 125.2(2) . . ?
C1 N1 C8 117.3(2) . . ?
C5 N1 C8 117.5(2) . . ?
O1 C1 N1 120.4(2) . . ?
O1 C1 C2 122.0(2) . . ?
N1 C1 C2 117.6(2) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 C7 120.4(2) . 3_666 ?
C1 C2 C7 119.9(2) . 3_666 ?
C6 C4 C3 120.9(2) . . ?
C6 C4 C5 119.1(2) . . ?
C3 C4 C5 119.9(2) . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 C3 120.4(3) . 3_666 ?
C4 C3 C3 118.1(3) . 3_666 ?
O2 C5 N1 119.6(2) . . ?
O2 C5 C4 124.6(2) . . ?
N1 C5 C4 115.9(2) . . ?
C7 C6 C4 121.6(2) . . ?
C7 C6 H6 119.2 . . ?
C4 C6 H6 119.2 . . ?
C6 C7 C2 118.5(2) . 3_666 ?
C6 C7 P1 120.1(2) . . ?
C2 C7 P1 121.2(2) 3_666 . ?
N1 C8 C9 113.8(5) . . ?
N1 C8 C9X 110.8(5) . . ?
N1 C8 H8A 106(2) . . ?
C9 C8 H8A 106(2) . . ?
C9X C8 H8A 115(2) . . ?
N1 C8 H8B 109(2) . . ?
C9 C8 H8B 115(2) . . ?
C9X C8 H8B 109(2) . . ?
H8A C8 H8B 107(3) . . ?
C10 C9 C12 113.8(8) . . ?
C10 C9 C8 123.9(8) . . ?
C12 C9 C8 113.4(8) . . ?
C10 C9 H9 100.0 . . ?
C12 C9 H9 100.0 . . ?
C8 C9 H9 100.0 . . ?
C11 C10 C9 121.7(9) . . ?
C11 C10 H10A 106.9 . . ?
C9 C10 H10A 106.9 . . ?
C11 C10 H10B 106.9 . . ?
C9 C10 H10B 106.9 . . ?
H10A C10 H10B 106.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C9 118.7(8) . . ?
C13 C12 H12A 107.6 . . ?
C9 C12 H12A 107.6 . . ?
C13 C12 H12B 107.6 . . ?
C9 C12 H12B 107.6 . . ?
H12A C12 H12B 107.1 . . ?
C14 C13 C12 126.0(9) . . ?
C14 C13 H13A 105.8 . . ?
C12 C13 H13A 105.8 . . ?
C14 C13 H13B 105.8 . . ?
C12 C13 H13B 105.8 . . ?
H13A C13 H13B 106.2 . . ?
C13 C14 C15 132.4(10) . . ?
C13 C14 H14A 104.1 . . ?
C15 C14 H14A 104.1 . . ?
C13 C14 H14B 104.1 . . ?
C15 C14 H14B 104.1 . . ?
H14A C14 H14B 105.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10X C9X C12X 113.3(9) . . ?
C10X C9X C8 106.1(7) . . ?
C12X C9X C8 101.5(8) . . ?
C10X C9X H9X 111.8 . . ?
C12X C9X H9X 111.8 . . ?
C8 C9X H9X 111.8 . . ?
C11X C10X C9X 111.3(9) . . ?
C11X C10X H10C 109.4 . . ?
C9X C10X H10C 109.4 . . ?
C11X C10X H10D 109.4 . . ?
C9X C10X H10D 109.4 . . ?
H10C C10X H10D 108.0 . . ?
C10X C11X H11E 109.5 . . ?
C10X C11X H11F 109.5 . . ?
H11E C11X H11F 109.5 . . ?
C10X C11X H11G 109.5 . . ?
H11E C11X H11G 109.5 . . ?
H11F C11X H11G 109.5 . . ?
C13X C12X C9X 114.6(10) . . ?
C13X C12X H12C 108.6 . . ?
C9X C12X H12C 108.6 . . ?
C13X C12X H12D 108.6 . . ?
C9X C12X H12D 108.6 . . ?
H12C C12X H12D 107.6 . . ?
C14X C13X C12X 131.3(10) . . ?
C14X C13X H13C 104.4 . . ?
C12X C13X H13C 104.4 . . ?
C14X C13X H13D 104.4 . . ?
C12X C13X H13D 104.4 . . ?
H13C C13X H13D 105.6 . . ?
C13X C14X C15X 119.9(8) . . ?
C13X C14X H14C 107.3 . . ?
C15X C14X H14C 107.3 . . ?
C13X C14X H14D 107.3 . . ?
C15X C14X H14D 107.3 . . ?
H14C C14X H14D 106.9 . . ?
C14X C15X H15E 109.5 . . ?
C14X C15X H15F 109.5 . . ?
H15E C15X H15F 109.5 . . ?
C14X C15X H15G 109.5 . . ?
H15E C15X H15G 109.5 . . ?
H15F C15X H15G 109.5 . . ?
C21 C16 C17 119.8(10) . . ?
C21 C16 P1 115.6(8) . . ?
C17 C16 P1 124.3(8) . . ?
C18 C17 C16 120.0(9) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.3(8) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.2(8) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.7(8) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C16 C21 C20 120.0(9) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21X C16X C17X 119.4(10) . . ?
C21X C16X P1 128.0(7) . . ?
C17X C16X P1 112.5(8) . . ?
C16X C17X C18X 120.6(9) . . ?
C16X C17X H17X 119.7 . . ?
C18X C17X H17X 119.7 . . ?
C19X C18X C17X 119.0(8) . . ?
C19X C18X H18X 120.5 . . ?
C17X C18X H18X 120.5 . . ?
C20X C19X C18X 120.2(9) . . ?
C20X C19X H19X 119.9 . . ?
C18X C19X H19X 119.9 . . ?
C19X C20X C21X 121.2(8) . . ?
C19X C20X H20X 119.4 . . ?
C21X C20X H20X 119.4 . . ?
C20X C21X C16X 119.6(8) . . ?
C20X C21X H21X 120.2 . . ?
C16X C21X H21X 120.2 . . ?
C27 C22 C23 119.0(3) . . ?
C27 C22 P1 123.4(3) . . ?
C23 C22 P1 117.6(2) . . ?
C24 C23 C22 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 119.7(3) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.3(4) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 120.5(3) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C22 119.8(3) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
C29 C28 C33 118.9(7) . . ?
C29 C28 P1 122.3(6) . . ?
C33 C28 P1 118.8(6) . . ?
C30 C29 C28 120.4(6) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.4(7) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C32 C31 C30 121.4(6) . . ?
C32 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
C33 C32 C31 118.4(6) . . ?
C33 C32 H32 120.8 . . ?
C31 C32 H32 120.8 . . ?
C32 C33 C28 121.5(8) . . ?
C32 C33 H33 119.3 . . ?
C28 C33 H33 119.3 . . ?
C33X C28X C29X 120.8(7) . . ?
C33X C28X P1 115.8(5) . . ?
C29X C28X P1 123.0(6) . . ?
C30X C29X C28X 119.3(7) . . ?
C30X C29X H29X 120.4 . . ?
C28X C29X H29X 120.4 . . ?
C31X C30X C29X 119.8(6) . . ?
C31X C30X H30X 120.1 . . ?
C29X C30X H30X 120.1 . . ?
C30X C31X C32X 122.2(7) . . ?
C30X C31X H31X 118.9 . . ?
C32X C31X H31X 118.9 . . ?
C33X C32X C31X 117.7(8) . . ?
C33X C32X H32X 121.1 . . ?
C31X C32X H32X 121.1 . . ?
C28X C33X C32X 120.2(6) . . ?
C28X C33X H33X 119.9 . . ?
C32X C33X H33X 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 O1 176.2(3) . . . . ?
C8 N1 C1 O1 -6.0(4) . . . . ?
C5 N1 C1 C2 -4.0(4) . . . . ?
C8 N1 C1 C2 173.8(3) . . . . ?
O1 C1 C2 C3 -176.1(3) . . . . ?
N1 C1 C2 C3 4.0(4) . . . . ?
O1 C1 C2 C7 3.4(4) . . . 3_666 ?
N1 C1 C2 C7 -176.5(3) . . . 3_666 ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C7 C2 C3 C4 179.6(3) 3_666 . . . ?
C1 C2 C3 C3 178.6(3) . . . 3_666 ?
C7 C2 C3 C3 -0.9(5) 3_666 . . 3_666 ?
C6 C4 C3 C2 179.1(3) . . . . ?
C5 C4 C3 C2 -2.7(4) . . . . ?
C6 C4 C3 C3 -0.4(5) . . . 3_666 ?
C5 C4 C3 C3 177.8(3) . . . 3_666 ?
C1 N1 C5 O2 179.7(3) . . . . ?
C8 N1 C5 O2 1.9(4) . . . . ?
C1 N1 C5 C4 0.6(4) . . . . ?
C8 N1 C5 C4 -177.2(3) . . . . ?
C6 C4 C5 O2 2.0(4) . . . . ?
C3 C4 C5 O2 -176.3(3) . . . . ?
C6 C4 C5 N1 -178.9(3) . . . . ?
C3 C4 C5 N1 2.8(4) . . . . ?
C3 C4 C6 C7 1.0(4) . . . . ?
C5 C4 C6 C7 -177.3(3) . . . . ?
C4 C6 C7 C2 -0.6(4) . . . 3_666 ?
C4 C6 C7 P1 -175.6(2) . . . . ?
C28X P1 C7 C6 -115.1(4) . . . . ?
C22 P1 C7 C6 113.8(3) . . . . ?
C16 P1 C7 C6 -8.4(4) . . . . ?
C16X P1 C7 C6 5.2(4) . . . . ?
C28 P1 C7 C6 -110.8(4) . . . . ?
C28X P1 C7 C2 70.0(5) . . . 3_666 ?
C22 P1 C7 C2 -61.1(3) . . . 3_666 ?
C16 P1 C7 C2 176.7(4) . . . 3_666 ?
C16X P1 C7 C2 -169.6(4) . . . 3_666 ?
C28 P1 C7 C2 74.3(4) . . . 3_666 ?
C1 N1 C8 C9 -85.7(6) . . . . ?
C5 N1 C8 C9 92.2(6) . . . . ?
C1 N1 C8 C9X -95.2(5) . . . . ?
C5 N1 C8 C9X 82.8(5) . . . . ?
N1 C8 C9 C10 45.9(14) . . . . ?
N1 C8 C9 C12 -169.0(8) . . . . ?
C12 C9 C10 C11 53(2) . . . . ?
C8 C9 C10 C11 -161.7(15) . . . . ?
C10 C9 C12 C13 -171.8(12) . . . . ?
C8 C9 C12 C13 39.4(16) . . . . ?
C9 C12 C13 C14 124.7(14) . . . . ?
C12 C13 C14 C15 -132.3(16) . . . . ?
N1 C8 C9X C10X 61.0(9) . . . . ?
N1 C8 C9X C12X 179.7(6) . . . . ?
C12X C9X C10X C11X 75.5(17) . . . . ?
C8 C9X C10X C11X -173.9(13) . . . . ?
C10X C9X C12X C13X -157.0(10) . . . . ?
C8 C9X C12X C13X 89.6(13) . . . . ?
C9X C12X C13X C14X 43.9(18) . . . . ?
C12X C13X C14X C15X 171.5(11) . . . . ?
C7 P1 C16 C21 121.6(8) . . . . ?
C22 P1 C16 C21 -0.9(9) . . . . ?
C28 P1 C16 C21 -127.2(8) . . . . ?
C7 P1 C16 C17 -63.5(10) . . . . ?
C22 P1 C16 C17 174.0(8) . . . . ?
C28 P1 C16 C17 47.6(10) . . . . ?
C21 C16 C17 C18 0.6(14) . . . . ?
P1 C16 C17 C18 -174.0(9) . . . . ?
C16 C17 C18 C19 1.2(14) . . . . ?
C17 C18 C19 C20 -2.0(13) . . . . ?
C18 C19 C20 C21 1.0(12) . . . . ?
C17 C16 C21 C20 -1.6(14) . . . . ?
P1 C16 C21 C20 173.5(8) . . . . ?
C19 C20 C21 C16 0.8(13) . . . . ?
C28X P1 C16X C21X -116.6(10) . . . . ?
C7 P1 C16X C21X 113.4(9) . . . . ?
C22 P1 C16X C21X -4.4(10) . . . . ?
C28X P1 C16X C17X 59.2(9) . . . . ?
C7 P1 C16X C17X -70.9(8) . . . . ?
C22 P1 C16X C17X 171.3(7) . . . . ?
C21X C16X C17X C18X 1.7(15) . . . . ?
P1 C16X C17X C18X -174.4(8) . . . . ?
C16X C17X C18X C19X 0.3(14) . . . . ?
C17X C18X C19X C20X -2.8(13) . . . . ?
C18X C19X C20X C21X 3.3(13) . . . . ?
C19X C20X C21X C16X -1.2(13) . . . . ?
C17X C16X C21X C20X -1.3(14) . . . . ?
P1 C16X C21X C20X 174.2(8) . . . . ?
C28X P1 C22 C27 0.9(4) . . . . ?
C7 P1 C22 C27 137.4(2) . . . . ?
C16 P1 C22 C27 -104.6(5) . . . . ?
C16X P1 C22 C27 -106.6(5) . . . . ?
C28 P1 C22 C27 7.8(4) . . . . ?
C28X P1 C22 C23 178.2(4) . . . . ?
C7 P1 C22 C23 -45.4(3) . . . . ?
C16 P1 C22 C23 72.7(5) . . . . ?
C16X P1 C22 C23 70.7(5) . . . . ?
C28 P1 C22 C23 -174.9(4) . . . . ?
C27 C22 C23 C24 1.8(4) . . . . ?
P1 C22 C23 C24 -175.6(2) . . . . ?
C22 C23 C24 C25 -0.9(5) . . . . ?
C23 C24 C25 C26 -0.7(5) . . . . ?
C24 C25 C26 C27 1.4(5) . . . . ?
C25 C26 C27 C22 -0.5(5) . . . . ?
C23 C22 C27 C26 -1.1(4) . . . . ?
P1 C22 C27 C26 176.2(2) . . . . ?
C7 P1 C28 C29 3.2(7) . . . . ?
C22 P1 C28 C29 134.6(6) . . . . ?
C16 P1 C28 C29 -104.9(7) . . . . ?
C7 P1 C28 C33 -179.2(5) . . . . ?
C22 P1 C28 C33 -47.9(7) . . . . ?
C16 P1 C28 C33 72.6(7) . . . . ?
C33 C28 C29 C30 1.3(11) . . . . ?
P1 C28 C29 C30 178.8(6) . . . . ?
C28 C29 C30 C31 1.2(10) . . . . ?
C29 C30 C31 C32 -2.3(9) . . . . ?
C30 C31 C32 C33 0.8(9) . . . . ?
C31 C32 C33 C28 1.8(10) . . . . ?
C29 C28 C33 C32 -2.8(11) . . . . ?
P1 C28 C33 C32 179.6(6) . . . . ?
C7 P1 C28X C33X 1.9(8) . . . . ?
C22 P1 C28X C33X 134.3(5) . . . . ?
C16X P1 C28X C33X -121.8(7) . . . . ?
C7 P1 C28X C29X 174.8(5) . . . . ?
C22 P1 C28X C29X -52.7(8) . . . . ?
C16X P1 C28X C29X 51.1(8) . . . . ?
C33X C28X C29X C30X -2.3(11) . . . . ?
P1 C28X C29X C30X -174.9(6) . . . . ?
C28X C29X C30X C31X 1.4(10) . . . . ?
C29X C30X C31X C32X 0.7(10) . . . . ?
C30X C31X C32X C33X -1.7(10) . . . . ?
C29X C28X C33X C32X 1.3(11) . . . . ?
P1 C28X C33X C32X 174.4(6) . . . . ?
C31X C32X C33X C28X 0.7(10) . . . . ?

_refine_diff_density_max         1.149
_refine_diff_density_min         -0.881
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_cu_i180_0m
_database_code_depnum_ccdc_archive 'CCDC 1871426'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
_audit_creation_date             2018-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C66 H66 N2 O4 P2, Br1'
_chemical_formula_sum            'C66 H66 Br1 N2 O4 P2'
_chemical_formula_weight         1095.72
_chemical_melting_point          ?
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'
Br Br -0.6763 1.2805 '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'

_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.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   24.7543(7)
_cell_length_b                   24.7543(7)
_cell_length_c                   30.0212(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     15931.6(10)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    89076
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.506
_cell_measurement_theta_min      3.595
_shelx_estimated_absorpt_T_max   0.804
_shelx_estimated_absorpt_T_min   0.705
_exptl_absorpt_coefficient_mu    1.553
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_correction_T_min  0.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.028
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5168
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.147
_exptl_transmission_factor_max   0.804
_exptl_transmission_factor_min   0.705
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            89076
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.506
_diffrn_reflns_theta_min         3.595
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APPEXII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5690
_reflns_number_total             6700
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.929
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         6700
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.1345
_refine_ls_restrained_S_all      2.005
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3998
_refine_ls_wR_factor_ref         0.4175
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Br2(0.11333) Br1(0.242) Br0A(0.14)
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C4(H4A,H4B), C5(H5A,H5B), C3AA(H3AA,H3AB), C5AA(H5AA,H5AB)
3.c Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C30(H30),
  C32(H32)
3.d Idealised Me refined as rotating group:
 C4AA(H4AA,H4AB,H4AC), C6AA(H6AA,H6AB,H6AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.42705(5) 0.00344(4) 0.13037(3) 0.0585(4) Uani 1 1 d . . . . .
O4 O 0.34718(16) -0.04694(19) -0.08421(9) 0.0774(8) Uani 1 1 d . . . . .
N5 N 0.34268(16) -0.04132(16) -0.00863(10) 0.0615(7) Uani 1 1 d . . . . .
C1 C 0.36861(18) -0.03345(17) 0.03393(10) 0.0580(8) Uani 1 1 d . . . . .
C2 C 0.3742(2) -0.0378(2) -0.04833(11) 0.0644(9) Uani 1 1 d . . . . .
C0AA C 0.43920(19) -0.02102(18) -0.04383(11) 0.0604(8) Uani 1 1 d . . . . .
C2AA C 0.43410(18) -0.01350(17) 0.03732(11) 0.0577(8) Uani 1 1 d . . . . .
C1AA C 0.47301(19) -0.01832(19) -0.08169(10) 0.0614(8) Uani 1 1 d . . . . .
H1AA H 0.452590 -0.028557 -0.109775 0.074 Uiso 1 1 calc R . . . .
C6 C 0.46813(18) -0.00880(17) -0.00118(10) 0.0570(8) Uani 1 1 d . . . . .
C7 C 0.46446(19) 0.00115(18) 0.07966(10) 0.0586(8) Uani 1 1 d . . . . .
C8 C 0.4892(2) 0.0383(2) 0.17108(11) 0.0633(9) Uani 1 1 d . . . . .
C10 C 0.2779(2) -0.0550(2) -0.01254(13) 0.0675(9) Uani 1 1 d . . . . .
H10A H 0.256301 -0.070246 0.016375 0.081 Uiso 1 1 calc R . . . .
H10B H 0.255641 -0.088103 -0.035056 0.081 Uiso 1 1 calc R . . . .
C11 C 0.3958(2) 0.0546(2) 0.12523(12) 0.0698(10) Uani 1 1 d . . . . .
C12 C 0.3738(2) -0.0719(2) 0.15326(13) 0.0668(9) Uani 1 1 d . . . . .
C13 C 0.5930(3) 0.0922(3) 0.22627(16) 0.0883(14) Uani 1 1 d . . . . .
H13 H 0.628833 0.110673 0.244856 0.106 Uiso 1 1 calc R . . . .
C14 C 0.5104(2) 0.0016(2) 0.19112(11) 0.0719(10) Uani 1 1 d . . . . .
H14 H 0.489220 -0.042135 0.185954 0.086 Uiso 1 1 calc R . . . .
C15 C 0.5623(3) 0.0286(3) 0.21847(13) 0.0838(13) Uani 1 1 d . . . . .
H15 H 0.576824 0.003531 0.231928 0.101 Uiso 1 1 calc R . . . .
C16 C 0.5197(2) 0.1017(2) 0.17920(15) 0.0760(10) Uani 1 1 d . . . . .
H16 H 0.505615 0.127252 0.165913 0.091 Uiso 1 1 calc R . . . .
C17 C 0.3421(3) 0.0428(3) 0.14873(17) 0.0842(13) Uani 1 1 d . . . . .
H17 H 0.321194 0.007252 0.167425 0.101 Uiso 1 1 calc R . . . .
C18 C 0.3583(2) -0.1264(2) 0.13039(17) 0.0778(11) Uani 1 1 d . . . . .
H18 H 0.369603 -0.125146 0.100016 0.093 Uiso 1 1 calc R . . . .
C19 C 0.3554(3) -0.0744(3) 0.19769(15) 0.0819(12) Uani 1 1 d . . . . .
H19 H 0.366156 -0.037090 0.213460 0.098 Uiso 1 1 calc R . . . .
C20 C 0.3213(3) -0.1318(4) 0.2184(2) 0.1004(19) Uani 1 1 d . . . . .
H20 H 0.307218 -0.133844 0.248107 0.120 Uiso 1 1 calc R . . . .
C21 C 0.4270(3) 0.1065(3) 0.09776(17) 0.0892(14) Uani 1 1 d . . . . .
H21 H 0.463058 0.113206 0.081839 0.107 Uiso 1 1 calc R . . . .
C22 C 0.5725(3) 0.1279(3) 0.20777(19) 0.0935(14) Uani 1 1 d . . . . .
H22 H 0.593526 0.171370 0.213860 0.112 Uiso 1 1 calc R . . . .
C23 C 0.3256(3) -0.1832(3) 0.1528(3) 0.0964(15) Uani 1 1 d . . . . .
H23 H 0.315466 -0.220949 0.137888 0.116 Uiso 1 1 calc R . . . .
C24 C 0.3079(3) -0.1847(3) 0.1967(2) 0.102(2) Uani 1 1 d . . . . .
H24 H 0.285999 -0.223564 0.211717 0.123 Uiso 1 1 calc R . . . .
C27 C 0.3204(4) 0.0835(4) 0.1442(2) 0.109(2) Uani 1 1 d . . . . .
H27 H 0.283472 0.075626 0.159402 0.131 Uiso 1 1 calc R . . . .
C30 C 0.4055(5) 0.1484(4) 0.0936(2) 0.118(3) Uani 1 1 d . . . . .
H30 H 0.426188 0.184273 0.075208 0.142 Uiso 1 1 calc R . . . .
C32 C 0.3508(5) 0.1352(5) 0.1183(3) 0.129(3) Uani 1 1 d . . . . .
H32 H 0.335319 0.163320 0.116566 0.155 Uiso 1 1 calc R . . . .
Br2 Br 0.333333 0.666667 0.11756(13) 0.0936(8) Uani 0.34 3 d S T P . .
O1 O 0.33612(14) -0.04271(14) 0.06726(8) 0.0643(7) Uani 1 1 d . . . . .
C3 C 0.2769(3) 0.0064(3) -0.0269(2) 0.0941(15) Uani 1 1 d . . . . .
H3 H 0.297994 0.020660 -0.056445 0.113 Uiso 1 1 calc R . . . .
C4 C 0.2083(4) -0.0114(5) -0.0320(4) 0.130(3) Uani 1 1 d . . . . .
H4A H 0.186306 -0.032419 -0.004222 0.156 Uiso 1 1 calc R . . . .
H4B H 0.206676 0.027639 -0.034460 0.156 Uiso 1 1 calc R . . . .
C5 C 0.3089(5) 0.0583(4) 0.0057(2) 0.111(2) Uani 1 1 d . . . . .
H5A H 0.350767 0.064556 0.012543 0.133 Uiso 1 1 calc R . . . .
H5B H 0.284633 0.047381 0.033758 0.133 Uiso 1 1 calc R . . . .
C3AA C 0.1744(4) -0.0504(4) -0.0684(4) 0.133(3) Uani 1 1 d . . . . .
H3AA H 0.172084 -0.091233 -0.064633 0.160 Uiso 1 1 calc R . . . .
H3AB H 0.197727 -0.031438 -0.096187 0.160 Uiso 1 1 calc R . . . .
C4AA C 0.3151(7) 0.1179(5) -0.0131(3) 0.151(4) Uani 1 1 d . . . . .
H4AA H 0.326083 0.121228 -0.044777 0.226 Uiso 1 1 calc GR . . . .
H4AB H 0.347905 0.153761 0.002982 0.226 Uiso 1 1 calc GR . . . .
H4AC H 0.275434 0.117263 -0.009801 0.226 Uiso 1 1 calc GR . . . .
C5AA C 0.1082(6) -0.0615(7) -0.0736(8) 0.241(11) Uani 1 1 d . . . . .
H5AA H 0.081906 -0.089732 -0.049470 0.290 Uiso 1 1 calc R . . . .
H5AB H 0.109268 -0.021277 -0.069747 0.290 Uiso 1 1 calc R . . . .
Br1 Br 0.2628(2) -0.2243(3) 0.32592(13) 0.1488(18) Uani 0.242 1 d . . . . .
Br0A Br 0.4709(5) 0.2587(6) -0.0189(6) 0.1892(6) Uani 0.14 1 d . . . . .
C6AA C 0.0800(11) -0.0877(11) -0.1150(10) 0.326(18) Uani 1 1 d . . . . .
H6AA H 0.096325 -0.055026 -0.137915 0.489 Uiso 1 1 calc GR . . . .
H6AB H 0.034692 -0.105597 -0.112632 0.489 Uiso 1 1 calc GR . . . .
H6AC H 0.089314 -0.120408 -0.123305 0.489 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C7 1.798(3) . ?
P1 C8 1.810(4) . ?
P1 C11 1.792(4) . ?
P1 C12 1.797(4) . ?
O4 C2 1.227(5) . ?
N5 C1 1.399(5) . ?
N5 C2 1.403(4) . ?
N5 C10 1.468(5) . ?
C1 C2AA 1.443(5) . ?
C1 O1 1.231(4) . ?
C2 C0AA 1.454(6) . ?
C0AA C1AA 1.393(5) . ?
C0AA C6 1.424(5) . ?
C2AA C6 1.400(5) . ?
C2AA C7 1.428(5) . ?
C1AA C7 1.386(6) 10_655 ?
C6 C6 1.413(8) 10_655 ?
C8 C14 1.395(6) . ?
C8 C16 1.379(6) . ?
C10 C3 1.593(7) . ?
C11 C17 1.401(7) . ?
C11 C21 1.390(8) . ?
C12 C18 1.386(7) . ?
C12 C19 1.401(6) . ?
C13 C15 1.383(9) . ?
C13 C22 1.340(9) . ?
C14 C15 1.382(7) . ?
C16 C22 1.420(8) . ?
C17 C27 1.365(8) . ?
C18 C23 1.395(8) . ?
C19 C20 1.384(8) . ?
C20 C24 1.348(11) . ?
C21 C30 1.389(8) . ?
C23 C24 1.382(11) . ?
C27 C32 1.357(14) . ?
C30 C32 1.431(14) . ?
C3 C4 1.533(10) . ?
C3 C5 1.488(11) . ?
C4 C3AA 1.421(14) . ?
C5 C4AA 1.515(9) . ?
C3AA C5AA 1.527(16) . ?
C5AA C6AA 1.42(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
C7 P1 C8 104.99(17) . . ?
C7 P1 C12 114.38(18) . . ?
C11 P1 C7 111.15(17) . . ?
C11 P1 C8 106.56(19) . . ?
C11 P1 C12 114.6(2) . . ?
C12 P1 C8 104.14(19) . . ?
C1 N5 C2 124.4(3) . . ?
C1 N5 C10 118.5(3) . . ?
C2 N5 C10 117.1(3) . . ?
N5 C1 C2AA 118.1(3) . . ?
O1 C1 N5 120.3(4) . . ?
O1 C1 C2AA 121.6(3) . . ?
O4 C2 N5 120.0(4) . . ?
O4 C2 C0AA 123.8(3) . . ?
N5 C2 C0AA 116.1(3) . . ?
C1AA C0AA C2 119.4(3) . . ?
C1AA C0AA C6 119.8(4) . . ?
C6 C0AA C2 120.8(3) . . ?
C6 C2AA C1 119.8(3) . . ?
C6 C2AA C7 119.7(3) . . ?
C7 C2AA C1 120.5(3) . . ?
C7 C1AA C0AA 122.0(3) 10_655 . ?
C2AA C6 C0AA 120.5(3) . . ?
C2AA C6 C6 121.1(4) . 10_655 ?
C6 C6 C0AA 118.4(4) 10_655 . ?
C2AA C7 P1 123.2(3) . . ?
C1AA C7 P1 117.8(3) 10_655 . ?
C1AA C7 C2AA 118.8(3) 10_655 . ?
C14 C8 P1 119.2(3) . . ?
C16 C8 P1 120.9(3) . . ?
C16 C8 C14 119.6(4) . . ?
N5 C10 C3 109.7(4) . . ?
C17 C11 P1 120.6(4) . . ?
C21 C11 P1 117.8(4) . . ?
C21 C11 C17 121.6(4) . . ?
C18 C12 P1 121.6(3) . . ?
C18 C12 C19 120.2(4) . . ?
C19 C12 P1 117.6(4) . . ?
C22 C13 C15 120.4(5) . . ?
C15 C14 C8 120.1(5) . . ?
C14 C15 C13 120.0(5) . . ?
C8 C16 C22 118.8(5) . . ?
C27 C17 C11 118.6(6) . . ?
C12 C18 C23 118.7(5) . . ?
C20 C19 C12 119.4(6) . . ?
C24 C20 C19 120.5(5) . . ?
C30 C21 C11 119.9(6) . . ?
C13 C22 C16 120.9(6) . . ?
C24 C23 C18 120.2(6) . . ?
C20 C24 C23 120.9(5) . . ?
C32 C27 C17 121.0(7) . . ?
C21 C30 C32 117.1(7) . . ?
C27 C32 C30 121.9(6) . . ?
C4 C3 C10 107.2(5) . . ?
C5 C3 C10 112.9(5) . . ?
C5 C3 C4 110.4(6) . . ?
C3AA C4 C3 117.8(8) . . ?
C3 C5 C4AA 110.2(7) . . ?
C4 C3AA C5AA 114.7(13) . . ?
C6AA C5AA C3AA 114(2) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 938.8 69.8 ?
2 0.333 0.667 0.667 938.8 69.8 ?
3 0.667 0.333 0.333 938.8 69.8 ?


_olex2_submission_special_instructions 'No special instructions were received'
