# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1540170'
_audit_update_record             
;
2017-03-25 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H27 O2 P'
_chemical_formula_weight         486.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   9.0757(2)
_cell_length_b                   10.4623(2)
_cell_length_c                   26.2445(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2491.99(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    4615
_cell_measurement_theta_min      4.8670
_cell_measurement_theta_max      71.1530

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.199
_shelx_estimated_absorpt_T_min   0.738
_shelx_estimated_absorpt_T_max   0.778
_exptl_absorpt_correction_T_min  0.76887
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            6126
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         4.550
_diffrn_reflns_theta_max         71.323
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_point_group_measured_fraction_full 0.909
_reflns_number_total             4244
_reflns_number_gt                4097
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.579
_reflns_Friedel_fraction_max     0.751
_reflns_Friedel_fraction_full    0.792

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

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013

_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)+(0.0524P)²+0.0971P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1486 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.136(12)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4244
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.046
_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
P1 P 0.68932(6) 0.32070(5) 0.68056(2) 0.03887(14) Uani 1 1 d . . . . .
O1 O 0.69631(19) 0.32686(17) 0.73701(6) 0.0531(4) Uani 1 1 d . . . . .
O2 O 0.2339(2) 0.69065(19) 0.61155(8) 0.0654(5) Uani 1 1 d . . . . .
C4 C 0.8344(2) 0.30512(19) 0.54930(8) 0.0368(4) Uani 1 1 d . . . . .
C16 C 0.7637(3) 0.0118(2) 0.59451(9) 0.0408(5) Uani 1 1 d . . . . .
C11 C 0.7588(2) 0.1377(2) 0.61580(8) 0.0371(4) Uani 1 1 d . . . . .
C21 C 0.5501(2) 0.4286(2) 0.65722(8) 0.0400(5) Uani 1 1 d . . . . .
C12 C 0.6581(2) 0.1661(2) 0.65315(8) 0.0389(4) Uani 1 1 d . . . . .
C24 C 0.3349(2) 0.6054(2) 0.62942(9) 0.0446(5) Uani 1 1 d . . . . .
C9 C 0.8684(2) 0.3435(2) 0.64671(8) 0.0380(4) Uani 1 1 d . . . . .
C10 C 0.8629(2) 0.24488(19) 0.60127(8) 0.0357(4) Uani 1 1 d . . . . .
H10 H 0.9612 0.2065 0.5994 0.043 Uiso 1 1 calc R U . . .
C3 C 0.9118(2) 0.4179(2) 0.53790(9) 0.0426(5) Uani 1 1 d . . . . .
C15 C 0.6588(3) -0.0793(2) 0.61244(9) 0.0455(5) Uani 1 1 d . . . . .
C25 C 0.3894(3) 0.5181(2) 0.59409(9) 0.0478(5) Uani 1 1 d . . . . .
H25 H 0.3537 0.5189 0.5609 0.057 Uiso 1 1 calc R U . . .
C13 C 0.5541(3) 0.0753(2) 0.67017(9) 0.0460(5) Uani 1 1 d . . . . .
H13 H 0.4852 0.0974 0.6949 0.055 Uiso 1 1 calc R U . . .
C8 C 0.8888(3) 0.4813(2) 0.62708(9) 0.0456(5) Uani 1 1 d . . . . .
H8A H 0.7937 0.5168 0.6179 0.055 Uiso 1 1 calc R U . . .
H8B H 0.9305 0.5339 0.6539 0.055 Uiso 1 1 calc R U . . .
C5 C 0.7481(3) 0.2490(2) 0.51175(9) 0.0434(5) Uani 1 1 d . . . . .
H5 H 0.6935 0.1761 0.5192 0.052 Uiso 1 1 calc R U . . .
C22 C 0.4928(3) 0.5145(2) 0.69226(9) 0.0489(5) Uani 1 1 d . . . . .
H22 H 0.5274 0.5126 0.7256 0.059 Uiso 1 1 calc R U . . .
C7 C 0.9905(3) 0.4831(2) 0.58076(10) 0.0484(6) Uani 1 1 d . . . . .
H7A H 1.0139 0.5705 0.5715 0.058 Uiso 1 1 calc R U . . .
H7B H 1.0816 0.4387 0.5884 0.058 Uiso 1 1 calc R U . . .
C26 C 0.4953(3) 0.4307(2) 0.60771(9) 0.0443(5) Uani 1 1 d . . . . .
H26 H 0.5304 0.3727 0.5838 0.053 Uiso 1 1 calc R U . . .
C20 C 0.8669(3) -0.0264(2) 0.55754(10) 0.0495(6) Uani 1 1 d . . . . .
H20 H 0.9367 0.0319 0.5460 0.059 Uiso 1 1 calc R U . . .
C23 C 0.3857(3) 0.6033(2) 0.67919(10) 0.0496(5) Uani 1 1 d . . . . .
H23 H 0.3489 0.6601 0.7033 0.059 Uiso 1 1 calc R U . . .
C14 C 0.5552(3) -0.0442(2) 0.65036(10) 0.0513(6) Uani 1 1 d . . . . .
H14 H 0.4871 -0.1041 0.6618 0.062 Uiso 1 1 calc R U . . .
C2 C 0.9036(3) 0.4692(2) 0.48932(10) 0.0533(6) Uani 1 1 d . . . . .
H2 H 0.9545 0.5441 0.4819 0.064 Uiso 1 1 calc R U . . .
C6 C 0.7431(3) 0.3013(3) 0.46318(10) 0.0543(6) Uani 1 1 d . . . . .
H6 H 0.6867 0.2623 0.4380 0.065 Uiso 1 1 calc R U . . .
C1 C 0.8215(4) 0.4112(3) 0.45191(10) 0.0609(7) Uani 1 1 d . . . . .
H1 H 0.8186 0.4455 0.4192 0.073 Uiso 1 1 calc R U . . .
C28 C 0.9900(2) 0.3059(2) 0.68494(9) 0.0440(5) Uani 1 1 d . . . . .
C17 C 0.6607(3) -0.2036(2) 0.59114(11) 0.0596(7) Uani 1 1 d . . . . .
H17 H 0.5926 -0.2640 0.6022 0.072 Uiso 1 1 calc R U . . .
C33 C 1.0495(3) 0.1835(2) 0.68757(11) 0.0541(6) Uani 1 1 d . . . . .
H33 H 1.0153 0.1209 0.6654 0.065 Uiso 1 1 calc R U . . .
C19 C 0.8666(4) -0.1477(2) 0.53821(11) 0.0616(7) Uani 1 1 d . . . . .
H19 H 0.9365 -0.1717 0.5141 0.074 Uiso 1 1 calc R U . . .
C18 C 0.7605(4) -0.2360(2) 0.55482(12) 0.0648(8) Uani 1 1 d . . . . .
H18 H 0.7585 -0.3176 0.5408 0.078 Uiso 1 1 calc R U . . .
C32 C 1.1587(3) 0.1529(3) 0.72257(12) 0.0654(7) Uani 1 1 d . . . . .
H32 H 1.1973 0.0705 0.7232 0.078 Uiso 1 1 calc R U . . .
C29 C 1.0425(3) 0.3940(3) 0.72029(12) 0.0631(7) Uani 1 1 d . . . . .
H29 H 1.0034 0.4761 0.7206 0.076 Uiso 1 1 calc R U . . .
C30 C 1.1512(4) 0.3625(4) 0.75494(13) 0.0780(9) Uani 1 1 d . . . . .
H30 H 1.1847 0.4240 0.7778 0.094 Uiso 1 1 calc R U . . .
C31 C 1.2102(3) 0.2424(3) 0.75610(13) 0.0711(8) Uani 1 1 d . . . . .
H31 H 1.2840 0.2219 0.7793 0.085 Uiso 1 1 calc R U . . .
C27 C 0.1599(3) 0.7699(3) 0.64755(15) 0.0756(9) Uani 1 1 d . . . . .
H27A H 0.0855 0.8191 0.6304 0.113 Uiso 1 1 calc R U . . .
H27B H 0.2296 0.8265 0.6633 0.113 Uiso 1 1 calc R U . . .
H27C H 0.1146 0.7174 0.6732 0.113 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 O1 1.4844(16) . ?
P1 C12 1.793(2) . ?
P1 C21 1.801(2) . ?
P1 C9 1.867(2) . ?
O2 C24 1.362(3) . ?
O2 C27 1.425(4) . ?
C4 C5 1.389(3) . ?
C4 C3 1.406(3) . ?
C4 C10 1.524(3) . ?
C16 C20 1.407(3) . ?
C16 C15 1.427(3) . ?
C16 C11 1.431(3) . ?
C11 C12 1.373(3) . ?
C11 C10 1.515(3) . ?
C21 C22 1.387(3) . ?
C21 C26 1.392(3) . ?
C12 C13 1.411(3) . ?
C24 C23 1.386(3) . ?
C24 C25 1.393(3) . ?
C9 C28 1.542(3) . ?
C9 C8 1.543(3) . ?
C9 C10 1.577(3) . ?
C10 H10 0.9800 . ?
C3 C2 1.385(3) . ?
C3 C7 1.497(3) . ?
C15 C17 1.416(3) . ?
C15 C14 1.417(4) . ?
C25 C26 1.374(3) . ?
C25 H25 0.9300 . ?
C13 C14 1.354(4) . ?
C13 H13 0.9300 . ?
C8 C7 1.526(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C22 C23 1.388(3) . ?
C22 H22 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C26 H26 0.9300 . ?
C20 C19 1.366(3) . ?
C20 H20 0.9300 . ?
C23 H23 0.9300 . ?
C14 H14 0.9300 . ?
C2 C1 1.374(4) . ?
C2 H2 0.9300 . ?
C6 C1 1.384(4) . ?
C6 H6 0.9300 . ?
C1 H1 0.9300 . ?
C28 C33 1.391(4) . ?
C28 C29 1.392(4) . ?
C17 C18 1.358(4) . ?
C17 H17 0.9300 . ?
C33 C32 1.389(4) . ?
C33 H33 0.9300 . ?
C19 C18 1.404(4) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C32 C31 1.368(5) . ?
C32 H32 0.9300 . ?
C29 C30 1.382(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.366(5) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C12 116.51(10) . . ?
O1 P1 C21 110.01(10) . . ?
C12 P1 C21 108.56(10) . . ?
O1 P1 C9 115.60(10) . . ?
C12 P1 C9 93.54(10) . . ?
C21 P1 C9 111.63(10) . . ?
C24 O2 C27 118.0(2) . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 C10 123.74(18) . . ?
C3 C4 C10 116.94(19) . . ?
C20 C16 C15 118.8(2) . . ?
C20 C16 C11 123.5(2) . . ?
C15 C16 C11 117.8(2) . . ?
C12 C11 C16 119.9(2) . . ?
C12 C11 C10 115.78(19) . . ?
C16 C11 C10 124.3(2) . . ?
C22 C21 C26 118.3(2) . . ?
C22 C21 P1 116.34(17) . . ?
C26 C21 P1 125.32(18) . . ?
C11 C12 C13 121.7(2) . . ?
C11 C12 P1 112.09(16) . . ?
C13 C12 P1 125.86(18) . . ?
O2 C24 C23 124.0(2) . . ?
O2 C24 C25 116.1(2) . . ?
C23 C24 C25 119.9(2) . . ?
C28 C9 C8 111.70(18) . . ?
C28 C9 C10 110.36(17) . . ?
C8 C9 C10 111.27(18) . . ?
C28 C9 P1 106.30(14) . . ?
C8 C9 P1 112.48(15) . . ?
C10 C9 P1 104.40(13) . . ?
C11 C10 C4 115.20(17) . . ?
C11 C10 C9 108.27(17) . . ?
C4 C10 C9 114.29(17) . . ?
C11 C10 H10 106.1 . . ?
C4 C10 H10 106.1 . . ?
C9 C10 H10 106.1 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 C7 122.8(2) . . ?
C4 C3 C7 117.4(2) . . ?
C17 C15 C14 121.6(2) . . ?
C17 C15 C16 118.4(2) . . ?
C14 C15 C16 120.0(2) . . ?
C26 C25 C24 120.8(2) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C7 C8 C9 110.47(18) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C21 C22 C23 122.2(2) . . ?
C21 C22 H22 118.9 . . ?
C23 C22 H22 118.9 . . ?
C3 C7 C8 107.73(18) . . ?
C3 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
C3 C7 H7B 110.2 . . ?
C8 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C25 C26 C21 120.2(2) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
C19 C20 C16 121.3(2) . . ?
C19 C20 H20 119.4 . . ?
C16 C20 H20 119.4 . . ?
C24 C23 C22 118.5(2) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C13 C14 C15 120.9(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C1 C2 C3 121.1(2) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C1 C6 C5 120.5(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C2 C1 C6 119.5(2) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C33 C28 C29 116.3(2) . . ?
C33 C28 C9 123.0(2) . . ?
C29 C28 C9 120.7(2) . . ?
C18 C17 C15 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C15 C17 H17 119.5 . . ?
C32 C33 C28 121.5(3) . . ?
C32 C33 H33 119.3 . . ?
C28 C33 H33 119.3 . . ?
C20 C19 C18 119.8(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C17 C18 C19 120.7(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C31 C32 C33 120.7(3) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C30 C29 C28 121.7(3) . . ?
C30 C29 H29 119.1 . . ?
C28 C29 H29 119.1 . . ?
C31 C30 C29 120.9(3) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C30 C31 C32 118.8(3) . . ?
C30 C31 H31 120.6 . . ?
C32 C31 H31 120.6 . . ?
O2 C27 H27A 109.5 . . ?
O2 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O2 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C20 C16 C11 C12 -177.5(2) . . . . ?
C15 C16 C11 C12 1.7(3) . . . . ?
C20 C16 C11 C10 0.2(3) . . . . ?
C15 C16 C11 C10 179.5(2) . . . . ?
O1 P1 C21 C22 11.4(2) . . . . ?
C12 P1 C21 C22 139.94(19) . . . . ?
C9 P1 C21 C22 -118.34(19) . . . . ?
O1 P1 C21 C26 -167.6(2) . . . . ?
C12 P1 C21 C26 -39.0(2) . . . . ?
C9 P1 C21 C26 62.7(2) . . . . ?
C16 C11 C12 C13 -2.4(3) . . . . ?
C10 C11 C12 C13 179.7(2) . . . . ?
C16 C11 C12 P1 171.50(16) . . . . ?
C10 C11 C12 P1 -6.4(2) . . . . ?
O1 P1 C12 C11 -129.34(16) . . . . ?
C21 P1 C12 C11 105.86(17) . . . . ?
C9 P1 C12 C11 -8.37(17) . . . . ?
O1 P1 C12 C13 44.2(2) . . . . ?
C21 P1 C12 C13 -80.6(2) . . . . ?
C9 P1 C12 C13 165.2(2) . . . . ?
C27 O2 C24 C23 -9.7(4) . . . . ?
C27 O2 C24 C25 171.4(2) . . . . ?
O1 P1 C9 C28 24.10(17) . . . . ?
C12 P1 C9 C28 -97.60(15) . . . . ?
C21 P1 C9 C28 150.83(14) . . . . ?
O1 P1 C9 C8 -98.44(17) . . . . ?
C12 P1 C9 C8 139.86(16) . . . . ?
C21 P1 C9 C8 28.29(19) . . . . ?
O1 P1 C9 C10 140.79(13) . . . . ?
C12 P1 C9 C10 19.09(14) . . . . ?
C21 P1 C9 C10 -92.47(15) . . . . ?
C12 C11 C10 C4 -108.0(2) . . . . ?
C16 C11 C10 C4 74.2(3) . . . . ?
C12 C11 C10 C9 21.4(3) . . . . ?
C16 C11 C10 C9 -156.47(19) . . . . ?
C5 C4 C10 C11 -16.3(3) . . . . ?
C3 C4 C10 C11 169.75(18) . . . . ?
C5 C4 C10 C9 -142.6(2) . . . . ?
C3 C4 C10 C9 43.4(2) . . . . ?
C28 C9 C10 C11 89.0(2) . . . . ?
C8 C9 C10 C11 -146.42(19) . . . . ?
P1 C9 C10 C11 -24.85(19) . . . . ?
C28 C9 C10 C4 -141.13(17) . . . . ?
C8 C9 C10 C4 -16.5(2) . . . . ?
P1 C9 C10 C4 105.02(16) . . . . ?
C5 C4 C3 C2 -1.6(3) . . . . ?
C10 C4 C3 C2 172.7(2) . . . . ?
C5 C4 C3 C7 173.6(2) . . . . ?
C10 C4 C3 C7 -12.1(3) . . . . ?
C20 C16 C15 C17 -1.7(3) . . . . ?
C11 C16 C15 C17 179.0(2) . . . . ?
C20 C16 C15 C14 178.8(2) . . . . ?
C11 C16 C15 C14 -0.5(3) . . . . ?
O2 C24 C25 C26 177.9(2) . . . . ?
C23 C24 C25 C26 -1.1(4) . . . . ?
C11 C12 C13 C14 1.8(3) . . . . ?
P1 C12 C13 C14 -171.24(19) . . . . ?
C28 C9 C8 C7 87.3(2) . . . . ?
C10 C9 C8 C7 -36.5(2) . . . . ?
P1 C9 C8 C7 -153.24(16) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
C10 C4 C5 C6 -171.5(2) . . . . ?
C26 C21 C22 C23 -1.4(4) . . . . ?
P1 C21 C22 C23 179.6(2) . . . . ?
C2 C3 C7 C8 132.4(2) . . . . ?
C4 C3 C7 C8 -42.6(3) . . . . ?
C9 C8 C7 C3 67.7(2) . . . . ?
C24 C25 C26 C21 -0.2(4) . . . . ?
C22 C21 C26 C25 1.4(4) . . . . ?
P1 C21 C26 C25 -179.62(18) . . . . ?
C15 C16 C20 C19 1.0(4) . . . . ?
C11 C16 C20 C19 -179.7(2) . . . . ?
O2 C24 C23 C22 -177.7(2) . . . . ?
C25 C24 C23 C22 1.2(4) . . . . ?
C21 C22 C23 C24 0.0(4) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C17 C15 C14 C13 -179.6(2) . . . . ?
C16 C15 C14 C13 -0.1(4) . . . . ?
C4 C3 C2 C1 -0.3(4) . . . . ?
C7 C3 C2 C1 -175.2(2) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
C3 C2 C1 C6 1.4(4) . . . . ?
C5 C6 C1 C2 -0.6(4) . . . . ?
C8 C9 C28 C33 -143.8(2) . . . . ?
C10 C9 C28 C33 -19.5(3) . . . . ?
P1 C9 C28 C33 93.1(2) . . . . ?
C8 C9 C28 C29 38.4(3) . . . . ?
C10 C9 C28 C29 162.8(2) . . . . ?
P1 C9 C28 C29 -84.6(3) . . . . ?
C14 C15 C17 C18 180.0(2) . . . . ?
C16 C15 C17 C18 0.5(4) . . . . ?
C29 C28 C33 C32 -2.0(4) . . . . ?
C9 C28 C33 C32 -179.9(2) . . . . ?
C16 C20 C19 C18 0.8(4) . . . . ?
C15 C17 C18 C19 1.4(4) . . . . ?
C20 C19 C18 C17 -2.1(4) . . . . ?
C28 C33 C32 C31 0.8(5) . . . . ?
C33 C28 C29 C30 2.1(4) . . . . ?
C9 C28 C29 C30 179.9(3) . . . . ?
C28 C29 C30 C31 -0.8(6) . . . . ?
C29 C30 C31 C32 -0.6(6) . . . . ?
C33 C32 C31 C30 0.6(5) . . . . ?

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-4



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

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1538597'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H25 O P'
_chemical_formula_weight         456.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           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                   12.38850(10)
_cell_length_b                   18.8197(2)
_cell_length_c                   10.45830(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.8280(10)
_cell_angle_gamma                90
_cell_volume                     2367.66(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    9261
_cell_measurement_theta_min      3.6700
_cell_measurement_theta_max      69.5040

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.196
_shelx_estimated_absorpt_T_min   0.653
_shelx_estimated_absorpt_T_max   0.754
_exptl_absorpt_correction_T_min  0.81651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            17473
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.674
_diffrn_reflns_theta_max         69.594
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4413
_reflns_number_gt                4039
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013

_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)+(0.0566P)²+0.5049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4413
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.72688(3) 0.17332(2) 0.25553(3) 0.03926(12) Uani 1 1 d . . . . .
O1 O 0.76995(9) 0.24712(5) 0.26798(11) 0.0519(3) Uani 1 1 d . . . . .
C11 C 0.79332(11) 0.05153(7) 0.17918(12) 0.0359(3) Uani 1 1 d . . . . .
C1 C 0.78512(11) 0.03680(7) 0.31859(12) 0.0364(3) Uani 1 1 d . . . . .
H1 H 0.8527 0.0111 0.3622 0.044 Uiso 1 1 calc R U . . .
C16 C 0.83241(11) 0.00118(7) 0.09935(13) 0.0382(3) Uani 1 1 d . . . . .
C21 C 0.90747(12) 0.13524(8) 0.44899(13) 0.0424(3) Uani 1 1 d . . . . .
C15 C 0.83573(11) 0.02176(8) -0.03085(13) 0.0414(3) Uani 1 1 d . . . . .
C3 C 0.66532(13) -0.01844(8) 0.45090(15) 0.0469(3) Uani 1 1 d . . . . .
C26 C 0.93283(15) 0.18493(8) 0.55096(16) 0.0530(4) Uani 1 1 d . . . . .
H26 H 0.8764 0.2026 0.5867 0.064 Uiso 1 1 calc R U . . .
C4 C 0.72662(14) 0.03012(9) 0.55670(15) 0.0530(4) Uani 1 1 d . . . . .
H4A H 0.8036 0.0153 0.5859 0.064 Uiso 1 1 calc R U . . .
H4B H 0.6932 0.0290 0.6316 0.064 Uiso 1 1 calc R U . . .
C17 C 0.87096(13) -0.06735(8) 0.14460(15) 0.0469(3) Uani 1 1 d . . . . .
H17 H 0.8684 -0.0815 0.2290 0.056 Uiso 1 1 calc R U . . .
C12 C 0.76224(11) 0.11844(7) 0.13169(13) 0.0386(3) Uani 1 1 d . . . . .
C30 C 0.34976(15) 0.17411(11) 0.2104(2) 0.0738(6) Uani 1 1 d . . . . .
H30 H 0.2734 0.1749 0.2023 0.089 Uiso 1 1 calc R U . . .
C7 C 0.62313(14) -0.04724(8) 0.22053(16) 0.0502(4) Uani 1 1 d . . . . .
H7 H 0.6357 -0.0410 0.1371 0.060 Uiso 1 1 calc R U . . .
C2 C 0.68687(12) -0.01032(7) 0.32644(14) 0.0405(3) Uani 1 1 d . . . . .
C20 C 0.87850(13) -0.02742(9) -0.10879(15) 0.0504(4) Uani 1 1 d . . . . .
H20 H 0.8813 -0.0148 -0.1939 0.060 Uiso 1 1 calc R U . . .
C13 C 0.76663(12) 0.13888(8) 0.00281(14) 0.0448(3) Uani 1 1 d . . . . .
H13 H 0.7457 0.1845 -0.0277 0.054 Uiso 1 1 calc R U . . .
C22 C 0.99530(13) 0.11171(9) 0.39793(17) 0.0546(4) Uani 1 1 d . . . . .
H22 H 0.9815 0.0786 0.3300 0.066 Uiso 1 1 calc R U . . .
C5 C 0.72009(13) 0.10527(8) 0.49919(15) 0.0482(3) Uani 1 1 d . . . . .
H5A H 0.7494 0.1390 0.5690 0.058 Uiso 1 1 calc R U . . .
H5B H 0.6430 0.1174 0.4609 0.058 Uiso 1 1 calc R U . . .
C10 C 0.58369(16) -0.06594(9) 0.46688(19) 0.0618(5) Uani 1 1 d . . . . .
H10 H 0.5700 -0.0722 0.5498 0.074 Uiso 1 1 calc R U . . .
C6 C 0.78723(11) 0.11034(7) 0.39245(13) 0.0385(3) Uani 1 1 d . . . . .
C18 C 0.91182(14) -0.11298(9) 0.06587(17) 0.0541(4) Uani 1 1 d . . . . .
H18 H 0.9373 -0.1577 0.0971 0.065 Uiso 1 1 calc R U . . .
C27 C 0.57704(13) 0.17256(8) 0.23132(16) 0.0466(3) Uani 1 1 d . . . . .
C9 C 0.52277(18) -0.10381(10) 0.3614(2) 0.0718(6) Uani 1 1 d . . . . .
H9 H 0.4696 -0.1363 0.3736 0.086 Uiso 1 1 calc R U . . .
C14 C 0.80180(13) 0.09116(9) -0.07583(14) 0.0473(3) Uani 1 1 d . . . . .
H14 H 0.8037 0.1043 -0.1610 0.057 Uiso 1 1 calc R U . . .
C19 C 0.91534(14) -0.09235(9) -0.06205(16) 0.0543(4) Uani 1 1 d . . . . .
H19 H 0.9432 -0.1236 -0.1152 0.065 Uiso 1 1 calc R U . . .
C25 C 1.04095(17) 0.20832(9) 0.59960(19) 0.0665(5) Uani 1 1 d . . . . .
H25 H 1.0561 0.2408 0.6687 0.080 Uiso 1 1 calc R U . . .
C24 C 1.12633(16) 0.18434(10) 0.5473(2) 0.0685(5) Uani 1 1 d . . . . .
H24 H 1.1986 0.2004 0.5803 0.082 Uiso 1 1 calc R U . . .
C8 C 0.54068(16) -0.09346(10) 0.2381(2) 0.0650(5) Uani 1 1 d . . . . .
H8 H 0.4974 -0.1175 0.1662 0.078 Uiso 1 1 calc R U . . .
C23 C 1.10284(14) 0.13648(10) 0.4459(2) 0.0652(5) Uani 1 1 d . . . . .
H23 H 1.1595 0.1204 0.4088 0.078 Uiso 1 1 calc R U . . .
C29 C 0.41619(16) 0.22156(11) 0.2905(3) 0.0813(7) Uani 1 1 d . . . . .
H29 H 0.3855 0.2541 0.3386 0.098 Uiso 1 1 calc R U . . .
C31 C 0.39481(16) 0.12520(13) 0.1416(2) 0.0758(6) Uani 1 1 d . . . . .
H31 H 0.3489 0.0925 0.0878 0.091 Uiso 1 1 calc R U . . .
C32 C 0.50823(14) 0.12399(10) 0.15140(17) 0.0605(4) Uani 1 1 d . . . . .
H32 H 0.5383 0.0905 0.1043 0.073 Uiso 1 1 calc R U . . .
C28 C 0.52952(15) 0.22131(10) 0.3004(2) 0.0704(5) Uani 1 1 d . . . . .
H28 H 0.5744 0.2544 0.3543 0.084 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 O1 1.4824(11) . ?
P1 C12 1.7909(14) . ?
P1 C27 1.8126(16) . ?
P1 C6 1.8715(14) . ?
C11 C12 1.3745(19) . ?
C11 C16 1.4222(19) . ?
C11 C1 1.5112(17) . ?
C1 C2 1.5239(18) . ?
C1 C6 1.5820(18) . ?
C1 H1 0.9800 . ?
C16 C17 1.417(2) . ?
C16 C15 1.4257(19) . ?
C21 C22 1.394(2) . ?
C21 C26 1.396(2) . ?
C21 C6 1.5386(19) . ?
C15 C20 1.417(2) . ?
C15 C14 1.418(2) . ?
C3 C10 1.389(2) . ?
C3 C2 1.398(2) . ?
C3 C4 1.495(2) . ?
C26 C25 1.386(3) . ?
C26 H26 0.9300 . ?
C4 C5 1.532(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C17 C18 1.368(2) . ?
C17 H17 0.9300 . ?
C12 C13 1.4151(19) . ?
C30 C29 1.359(3) . ?
C30 C31 1.367(3) . ?
C30 H30 0.9300 . ?
C7 C2 1.384(2) . ?
C7 C8 1.387(2) . ?
C7 H7 0.9300 . ?
C20 C19 1.354(2) . ?
C20 H20 0.9300 . ?
C13 C14 1.358(2) . ?
C13 H13 0.9300 . ?
C22 C23 1.387(2) . ?
C22 H22 0.9300 . ?
C5 C6 1.5463(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C10 C9 1.377(3) . ?
C10 H10 0.9300 . ?
C18 C19 1.404(2) . ?
C18 H18 0.9300 . ?
C27 C28 1.383(2) . ?
C27 C32 1.386(2) . ?
C9 C8 1.374(3) . ?
C9 H9 0.9300 . ?
C14 H14 0.9300 . ?
C19 H19 0.9300 . ?
C25 C24 1.378(3) . ?
C25 H25 0.9300 . ?
C24 C23 1.368(3) . ?
C24 H24 0.9300 . ?
C8 H8 0.9300 . ?
C23 H23 0.9300 . ?
C29 C28 1.383(3) . ?
C29 H29 0.9300 . ?
C31 C32 1.384(3) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C12 117.30(7) . . ?
O1 P1 C27 110.78(7) . . ?
C12 P1 C27 108.29(7) . . ?
O1 P1 C6 117.17(6) . . ?
C12 P1 C6 93.79(6) . . ?
C27 P1 C6 108.08(7) . . ?
C12 C11 C16 120.24(12) . . ?
C12 C11 C1 116.04(12) . . ?
C16 C11 C1 123.71(12) . . ?
C11 C1 C2 113.42(11) . . ?
C11 C1 C6 108.28(10) . . ?
C2 C1 C6 113.77(11) . . ?
C11 C1 H1 107.0 . . ?
C2 C1 H1 107.0 . . ?
C6 C1 H1 107.0 . . ?
C17 C16 C11 123.04(12) . . ?
C17 C16 C15 118.81(13) . . ?
C11 C16 C15 118.12(13) . . ?
C22 C21 C26 116.85(14) . . ?
C22 C21 C6 121.91(13) . . ?
C26 C21 C6 121.19(14) . . ?
C20 C15 C14 122.20(13) . . ?
C20 C15 C16 118.17(14) . . ?
C14 C15 C16 119.56(13) . . ?
C10 C3 C2 119.26(15) . . ?
C10 C3 C4 124.05(14) . . ?
C2 C3 C4 116.48(13) . . ?
C25 C26 C21 120.95(17) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
C3 C4 C5 107.70(12) . . ?
C3 C4 H4A 110.2 . . ?
C5 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
C5 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C18 C17 C16 120.94(14) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C11 C12 C13 121.47(13) . . ?
C11 C12 P1 111.27(10) . . ?
C13 C12 P1 127.14(11) . . ?
C29 C30 C31 120.25(18) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C2 C7 C8 120.44(15) . . ?
C2 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C2 C3 119.39(13) . . ?
C7 C2 C1 124.02(12) . . ?
C3 C2 C1 116.52(13) . . ?
C19 C20 C15 121.45(14) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
C14 C13 C12 119.21(13) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C23 C22 C21 121.65(16) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C4 C5 C6 110.70(12) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C9 C10 C3 120.78(16) . . ?
C9 C10 H10 119.6 . . ?
C3 C10 H10 119.6 . . ?
C21 C6 C5 112.32(11) . . ?
C21 C6 C1 110.83(11) . . ?
C5 C6 C1 110.46(11) . . ?
C21 C6 P1 105.91(9) . . ?
C5 C6 P1 113.95(10) . . ?
C1 C6 P1 102.91(8) . . ?
C17 C18 C19 120.02(15) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C28 C27 C32 118.38(16) . . ?
C28 C27 P1 118.11(12) . . ?
C32 C27 P1 123.46(13) . . ?
C8 C9 C10 119.88(16) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C13 C14 C15 121.40(13) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C20 C19 C18 120.60(14) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C24 C25 C26 121.10(17) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C23 C24 C25 118.81(17) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C9 C8 C7 120.16(17) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C24 C23 C22 120.63(18) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C30 C29 C28 119.88(19) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C30 C31 C32 120.47(18) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C31 C32 C27 120.06(18) . . ?
C31 C32 H32 120.0 . . ?
C27 C32 H32 120.0 . . ?
C29 C28 C27 120.95(17) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?

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
C12 C11 C1 C2 105.46(14) . . . . ?
C16 C11 C1 C2 -75.72(16) . . . . ?
C12 C11 C1 C6 -21.81(16) . . . . ?
C16 C11 C1 C6 157.02(12) . . . . ?
C12 C11 C16 C17 176.73(13) . . . . ?
C1 C11 C16 C17 -2.0(2) . . . . ?
C12 C11 C16 C15 -1.40(19) . . . . ?
C1 C11 C16 C15 179.82(12) . . . . ?
C17 C16 C15 C20 -0.50(19) . . . . ?
C11 C16 C15 C20 177.71(12) . . . . ?
C17 C16 C15 C14 -177.41(13) . . . . ?
C11 C16 C15 C14 0.81(19) . . . . ?
C22 C21 C26 C25 -1.1(2) . . . . ?
C6 C21 C26 C25 -178.59(15) . . . . ?
C10 C3 C4 C5 -129.26(16) . . . . ?
C2 C3 C4 C5 45.44(18) . . . . ?
C11 C16 C17 C18 -177.44(14) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C11 C12 C13 0.9(2) . . . . ?
C1 C11 C12 C13 179.72(12) . . . . ?
C16 C11 C12 P1 -175.44(10) . . . . ?
C1 C11 C12 P1 3.43(15) . . . . ?
O1 P1 C12 C11 136.07(10) . . . . ?
C27 P1 C12 C11 -97.69(11) . . . . ?
C6 P1 C12 C11 12.76(11) . . . . ?
O1 P1 C12 C13 -39.97(15) . . . . ?
C27 P1 C12 C13 86.27(14) . . . . ?
C6 P1 C12 C13 -163.27(13) . . . . ?
C8 C7 C2 C3 -1.8(2) . . . . ?
C8 C7 C2 C1 174.83(15) . . . . ?
C10 C3 C2 C7 2.9(2) . . . . ?
C4 C3 C2 C7 -172.02(14) . . . . ?
C10 C3 C2 C1 -173.96(14) . . . . ?
C4 C3 C2 C1 11.07(19) . . . . ?
C11 C1 C2 C7 11.51(19) . . . . ?
C6 C1 C2 C7 135.85(14) . . . . ?
C11 C1 C2 C3 -171.75(12) . . . . ?
C6 C1 C2 C3 -47.41(16) . . . . ?
C14 C15 C20 C19 176.90(14) . . . . ?
C16 C15 C20 C19 0.1(2) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
P1 C12 C13 C14 176.01(11) . . . . ?
C26 C21 C22 C23 -0.1(2) . . . . ?
C6 C21 C22 C23 177.42(15) . . . . ?
C3 C4 C5 C6 -67.68(16) . . . . ?
C2 C3 C10 C9 -1.2(3) . . . . ?
C4 C3 C10 C9 173.31(17) . . . . ?
C22 C21 C6 C5 147.20(15) . . . . ?
C26 C21 C6 C5 -35.40(18) . . . . ?
C22 C21 C6 C1 23.11(19) . . . . ?
C26 C21 C6 C1 -159.49(13) . . . . ?
C22 C21 C6 P1 -87.82(15) . . . . ?
C26 C21 C6 P1 89.58(14) . . . . ?
C4 C5 C6 C21 -92.70(15) . . . . ?
C4 C5 C6 C1 31.60(16) . . . . ?
C4 C5 C6 P1 146.86(11) . . . . ?
C11 C1 C6 C21 -84.91(13) . . . . ?
C2 C1 C6 C21 148.03(11) . . . . ?
C11 C1 C6 C5 149.95(11) . . . . ?
C2 C1 C6 C5 22.88(16) . . . . ?
C11 C1 C6 P1 27.94(12) . . . . ?
C2 C1 C6 P1 -99.13(11) . . . . ?
O1 P1 C6 C21 -30.20(11) . . . . ?
C12 P1 C6 C21 93.21(10) . . . . ?
C27 P1 C6 C21 -156.15(9) . . . . ?
O1 P1 C6 C5 93.77(11) . . . . ?
C12 P1 C6 C5 -142.82(11) . . . . ?
C27 P1 C6 C5 -32.18(12) . . . . ?
O1 P1 C6 C1 -146.61(8) . . . . ?
C12 P1 C6 C1 -23.20(9) . . . . ?
C27 P1 C6 C1 87.44(9) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
O1 P1 C27 C28 -38.51(17) . . . . ?
C12 P1 C27 C28 -168.46(15) . . . . ?
C6 P1 C27 C28 91.11(15) . . . . ?
O1 P1 C27 C32 144.12(14) . . . . ?
C12 P1 C27 C32 14.17(17) . . . . ?
C6 P1 C27 C32 -86.26(16) . . . . ?
C3 C10 C9 C8 -1.6(3) . . . . ?
C12 C13 C14 C15 -1.0(2) . . . . ?
C20 C15 C14 C13 -176.40(14) . . . . ?
C16 C15 C14 C13 0.4(2) . . . . ?
C15 C20 C19 C18 0.2(2) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C21 C26 C25 C24 1.2(3) . . . . ?
C26 C25 C24 C23 -0.2(3) . . . . ?
C10 C9 C8 C7 2.7(3) . . . . ?
C2 C7 C8 C9 -1.0(3) . . . . ?
C25 C24 C23 C22 -1.0(3) . . . . ?
C21 C22 C23 C24 1.1(3) . . . . ?
C31 C30 C29 C28 1.3(4) . . . . ?
C29 C30 C31 C32 -0.8(4) . . . . ?
C30 C31 C32 C27 0.0(3) . . . . ?
C28 C27 C32 C31 0.3(3) . . . . ?
P1 C27 C32 C31 177.67(16) . . . . ?
C30 C29 C28 C27 -1.0(4) . . . . ?
C32 C27 C28 C29 0.2(3) . . . . ?
P1 C27 C28 C29 -177.29(18) . . . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4



