# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2022

####################################################################### 
# 
# 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_PPPO
_database_code_depnum_ccdc_archive 'CCDC 2095821'
loop_
_audit_author_name
_audit_author_address
'Darina Nasyrova'
;N D Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-07-12 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H25 O P'
_chemical_formula_sum            'C34 H25 O P'
_chemical_formula_weight         480.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   16.0559(6)
_cell_length_b                   6.2918(2)
_cell_length_c                   24.2227(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.7170(10)
_cell_angle_gamma                90
_cell_volume                     2444.24(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      34.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7029
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            49922
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.060
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7133
_reflns_number_gt                5580
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²+4.3241P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7133
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1378
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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 0.31369(3) 0.13057(8) 0.33548(2) 0.01300(11) Uani 1 1 d . . . . .
O1 O 0.30405(9) -0.0906(2) 0.31437(6) 0.0193(3) Uani 1 1 d . . . . .
C1 C 0.28728(11) 0.1716(3) 0.40666(8) 0.0140(3) Uani 1 1 d . . . . .
C2 C 0.22331(11) 0.3116(3) 0.40758(8) 0.0143(3) Uani 1 1 d . . . . .
C3 C 0.19605(11) 0.3995(3) 0.35173(8) 0.0132(3) Uani 1 1 d . . . . .
C4 C 0.23945(11) 0.3250(3) 0.30903(8) 0.0135(3) Uani 1 1 d . . . . .
C5 C 0.41744(11) 0.2286(3) 0.32767(8) 0.0146(3) Uani 1 1 d . . . . .
C6 C 0.43994(13) 0.4390(3) 0.33831(9) 0.0214(4) Uani 1 1 d . . . . .
H6 H 0.399091 0.539979 0.347951 0.026 Uiso 1 1 calc R U . . .
C7 C 0.52264(14) 0.4998(4) 0.33470(10) 0.0267(5) Uani 1 1 d . . . . .
H7 H 0.538584 0.642592 0.342352 0.032 Uiso 1 1 calc R U . . .
C8 C 0.58206(13) 0.3530(4) 0.31997(10) 0.0257(5) Uani 1 1 d . . . . .
H8 H 0.638635 0.395530 0.318136 0.031 Uiso 1 1 calc R U . . .
C9 C 0.55979(13) 0.1457(4) 0.30795(9) 0.0234(4) Uani 1 1 d . . . . .
H9 H 0.600626 0.046885 0.297047 0.028 Uiso 1 1 calc R U . . .
C10 C 0.47735(12) 0.0820(3) 0.31185(8) 0.0186(4) Uani 1 1 d . . . . .
H10 H 0.461741 -0.060741 0.303807 0.022 Uiso 1 1 calc R U . . .
C11 C 0.33158(12) 0.0580(3) 0.45230(8) 0.0163(4) Uani 1 1 d . . . . .
C12 C 0.36636(13) -0.1426(4) 0.44232(9) 0.0228(4) Uani 1 1 d . . . . .
H12 H 0.359106 -0.204855 0.406689 0.027 Uiso 1 1 calc R U . . .
C13 C 0.41123(15) -0.2511(4) 0.48395(10) 0.0300(5) Uani 1 1 d . . . . .
H13 H 0.434143 -0.386782 0.476606 0.036 Uiso 1 1 calc R U . . .
C14 C 0.42266(15) -0.1625(4) 0.53590(10) 0.0309(5) Uani 1 1 d . . . . .
H14 H 0.453240 -0.236979 0.564322 0.037 Uiso 1 1 calc R U . . .
C15 C 0.38916(15) 0.0360(4) 0.54631(9) 0.0301(5) Uani 1 1 d . . . . .
H15 H 0.397242 0.097655 0.581963 0.036 Uiso 1 1 calc R U . . .
C16 C 0.34395(13) 0.1455(4) 0.50510(9) 0.0235(4) Uani 1 1 d . . . . .
H16 H 0.321222 0.281081 0.512870 0.028 Uiso 1 1 calc R U . . .
C17 C 0.17514(11) 0.3596(3) 0.45729(8) 0.0149(3) Uani 1 1 d . . . . .
C18 C 0.17828(13) 0.5573(3) 0.48339(8) 0.0197(4) Uani 1 1 d . . . . .
H18 H 0.212558 0.666623 0.469763 0.024 Uiso 1 1 calc R U . . .
C19 C 0.13135(14) 0.5952(4) 0.52939(9) 0.0230(4) Uani 1 1 d . . . . .
H19 H 0.134013 0.730060 0.547019 0.028 Uiso 1 1 calc R U . . .
C20 C 0.08083(14) 0.4371(4) 0.54951(9) 0.0233(4) Uani 1 1 d . . . . .
H20 H 0.047990 0.464411 0.580340 0.028 Uiso 1 1 calc R U . . .
C21 C 0.07848(13) 0.2393(4) 0.52446(9) 0.0224(4) Uani 1 1 d . . . . .
H21 H 0.044682 0.129889 0.538531 0.027 Uiso 1 1 calc R U . . .
C22 C 0.12552(12) 0.2003(3) 0.47868(8) 0.0181(4) Uani 1 1 d . . . . .
H22 H 0.123813 0.063856 0.461860 0.022 Uiso 1 1 calc R U . . .
C23 C 0.12202(11) 0.5404(3) 0.34388(7) 0.0138(3) Uani 1 1 d . . . . .
C24 C 0.12207(13) 0.7501(3) 0.36298(8) 0.0174(4) Uani 1 1 d . . . . .
H24 H 0.169540 0.805217 0.383052 0.021 Uiso 1 1 calc R U . . .
C25 C 0.05244(13) 0.8774(3) 0.35250(8) 0.0201(4) Uani 1 1 d . . . . .
H25 H 0.052517 1.019689 0.365626 0.024 Uiso 1 1 calc R U . . .
C26 C -0.01716(13) 0.7993(4) 0.32311(8) 0.0211(4) Uani 1 1 d . . . . .
H26 H -0.064419 0.887819 0.316094 0.025 Uiso 1 1 calc R U . . .
C27 C -0.01756(12) 0.5921(4) 0.30402(8) 0.0196(4) Uani 1 1 d . . . . .
H27 H -0.065209 0.538028 0.283925 0.024 Uiso 1 1 calc R U . . .
C28 C 0.05172(12) 0.4628(3) 0.31422(8) 0.0163(4) Uani 1 1 d . . . . .
H28 H 0.051243 0.320700 0.300927 0.020 Uiso 1 1 calc R U . . .
C29 C 0.23117(11) 0.3796(3) 0.24976(7) 0.0141(3) Uani 1 1 d . . . . .
C30 C 0.21303(11) 0.5867(3) 0.23133(8) 0.0156(4) Uani 1 1 d . . . . .
H30 H 0.204007 0.696325 0.257352 0.019 Uiso 1 1 calc R U . . .
C31 C 0.20823(12) 0.6318(3) 0.17518(8) 0.0179(4) Uani 1 1 d . . . . .
H31 H 0.194991 0.771933 0.163048 0.021 Uiso 1 1 calc R U . . .
C32 C 0.22256(13) 0.4745(4) 0.13648(8) 0.0196(4) Uani 1 1 d . . . . .
H32 H 0.219784 0.507059 0.098146 0.024 Uiso 1 1 calc R U . . .
C33 C 0.24097(13) 0.2694(4) 0.15429(8) 0.0208(4) Uani 1 1 d . . . . .
H33 H 0.250614 0.161090 0.128025 0.025 Uiso 1 1 calc R U . . .
C34 C 0.24536(12) 0.2218(3) 0.21054(8) 0.0176(4) Uani 1 1 d . . . . .
H34 H 0.258079 0.081028 0.222383 0.021 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 1.4882(15) . ?
P1 C5 1.7947(19) . ?
P1 C4 1.8043(19) . ?
P1 C1 1.8134(19) . ?
C1 C2 1.354(3) . ?
C1 C11 1.471(3) . ?
C2 C17 1.493(3) . ?
C2 C3 1.507(3) . ?
C3 C4 1.358(3) . ?
C3 C23 1.488(3) . ?
C4 C29 1.476(3) . ?
C5 C6 1.393(3) . ?
C5 C10 1.399(3) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.398(3) . ?
C11 C12 1.406(3) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.395(3) . ?
C17 C22 1.396(3) . ?
C18 C19 1.395(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.393(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.397(3) . ?
C23 C24 1.398(3) . ?
C24 C25 1.389(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.383(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.391(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C34 1.400(3) . ?
C29 C30 1.404(3) . ?
C30 C31 1.388(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.390(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.388(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.394(3) . ?
C33 H33 0.9500 . ?
C34 H34 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
O1 P1 C5 111.53(9) . . ?
O1 P1 C4 117.12(9) . . ?
C5 P1 C4 109.29(9) . . ?
O1 P1 C1 115.77(9) . . ?
C5 P1 C1 108.14(9) . . ?
C4 P1 C1 93.48(9) . . ?
C2 C1 C11 130.08(17) . . ?
C2 C1 P1 108.67(14) . . ?
C11 C1 P1 121.24(14) . . ?
C1 C2 C17 124.58(17) . . ?
C1 C2 C3 114.34(16) . . ?
C17 C2 C3 120.68(16) . . ?
C4 C3 C23 122.96(17) . . ?
C4 C3 C2 114.80(16) . . ?
C23 C3 C2 121.98(16) . . ?
C3 C4 C29 129.40(17) . . ?
C3 C4 P1 108.53(14) . . ?
C29 C4 P1 122.05(14) . . ?
C6 C5 C10 120.10(18) . . ?
C6 C5 P1 122.74(15) . . ?
C10 C5 P1 117.12(15) . . ?
C7 C6 C5 119.4(2) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 119.7(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C5 119.8(2) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?
C16 C11 C12 118.07(19) . . ?
C16 C11 C1 122.59(19) . . ?
C12 C11 C1 119.28(18) . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.5(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C18 C17 C22 118.77(18) . . ?
C18 C17 C2 122.49(18) . . ?
C22 C17 C2 118.74(18) . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 119.67(19) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.6(2) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
C28 C23 C24 119.21(18) . . ?
C28 C23 C3 118.58(17) . . ?
C24 C23 C3 122.15(18) . . ?
C25 C24 C23 119.73(19) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C26 C25 C24 120.78(19) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C27 C26 C25 119.78(19) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C28 120.06(19) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C23 120.44(19) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
C34 C29 C30 118.73(17) . . ?
C34 C29 C4 118.99(17) . . ?
C30 C29 C4 122.22(17) . . ?
C31 C30 C29 120.18(18) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 120.78(19) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C33 C32 C31 119.49(18) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C32 C33 C34 120.26(19) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C33 C34 C29 120.55(19) . . ?
C33 C34 H34 119.7 . . ?
C29 C34 H34 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 C1 C2 -118.58(14) . . . . ?
C5 P1 C1 C2 115.47(15) . . . . ?
C4 P1 C1 C2 3.87(15) . . . . ?
O1 P1 C1 C11 60.16(18) . . . . ?
C5 P1 C1 C11 -65.79(17) . . . . ?
C4 P1 C1 C11 -177.39(16) . . . . ?
C11 C1 C2 C17 -8.8(3) . . . . ?
P1 C1 C2 C17 169.78(15) . . . . ?
C11 C1 C2 C3 178.44(19) . . . . ?
P1 C1 C2 C3 -3.0(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C17 C2 C3 C4 -172.93(17) . . . . ?
C1 C2 C3 C23 174.51(17) . . . . ?
C17 C2 C3 C23 1.5(3) . . . . ?
C23 C3 C4 C29 7.3(3) . . . . ?
C2 C3 C4 C29 -178.37(18) . . . . ?
C23 C3 C4 P1 -171.53(15) . . . . ?
C2 C3 C4 P1 2.8(2) . . . . ?
O1 P1 C4 C3 117.59(14) . . . . ?
C5 P1 C4 C3 -114.38(14) . . . . ?
C1 P1 C4 C3 -3.78(15) . . . . ?
O1 P1 C4 C29 -61.35(18) . . . . ?
C5 P1 C4 C29 66.69(17) . . . . ?
C1 P1 C4 C29 177.28(16) . . . . ?
O1 P1 C5 C6 172.42(16) . . . . ?
C4 P1 C5 C6 41.33(19) . . . . ?
C1 P1 C5 C6 -59.18(19) . . . . ?
O1 P1 C5 C10 -9.64(18) . . . . ?
C4 P1 C5 C10 -140.73(15) . . . . ?
C1 P1 C5 C10 118.76(16) . . . . ?
C10 C5 C6 C7 -1.9(3) . . . . ?
P1 C5 C6 C7 175.94(17) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C9 0.9(4) . . . . ?
C7 C8 C9 C10 -1.5(3) . . . . ?
C8 C9 C10 C5 0.3(3) . . . . ?
C6 C5 C10 C9 1.4(3) . . . . ?
P1 C5 C10 C9 -176.61(16) . . . . ?
C2 C1 C11 C16 -32.6(3) . . . . ?
P1 C1 C11 C16 148.95(17) . . . . ?
C2 C1 C11 C12 150.3(2) . . . . ?
P1 C1 C11 C12 -28.1(3) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C1 C11 C12 C13 177.6(2) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C11 -0.2(4) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
C1 C11 C16 C15 -177.3(2) . . . . ?
C1 C2 C17 C18 113.0(2) . . . . ?
C3 C2 C17 C18 -74.7(2) . . . . ?
C1 C2 C17 C22 -66.5(3) . . . . ?
C3 C2 C17 C22 105.8(2) . . . . ?
C22 C17 C18 C19 -1.2(3) . . . . ?
C2 C17 C18 C19 179.28(19) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 1.4(3) . . . . ?
C19 C20 C21 C22 -1.1(3) . . . . ?
C20 C21 C22 C17 -0.4(3) . . . . ?
C18 C17 C22 C21 1.5(3) . . . . ?
C2 C17 C22 C21 -178.95(18) . . . . ?
C4 C3 C23 C28 62.4(3) . . . . ?
C2 C3 C23 C28 -111.5(2) . . . . ?
C4 C3 C23 C24 -114.6(2) . . . . ?
C2 C3 C23 C24 71.5(2) . . . . ?
C28 C23 C24 C25 0.3(3) . . . . ?
C3 C23 C24 C25 177.32(17) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C24 C25 C26 C27 0.1(3) . . . . ?
C25 C26 C27 C28 -0.1(3) . . . . ?
C26 C27 C28 C23 0.2(3) . . . . ?
C24 C23 C28 C27 -0.3(3) . . . . ?
C3 C23 C28 C27 -177.42(17) . . . . ?
C3 C4 C29 C34 -145.9(2) . . . . ?
P1 C4 C29 C34 32.8(2) . . . . ?
C3 C4 C29 C30 36.9(3) . . . . ?
P1 C4 C29 C30 -144.42(16) . . . . ?
C34 C29 C30 C31 0.9(3) . . . . ?
C4 C29 C30 C31 178.12(17) . . . . ?
C29 C30 C31 C32 -1.1(3) . . . . ?
C30 C31 C32 C33 0.7(3) . . . . ?
C31 C32 C33 C34 -0.2(3) . . . . ?
C32 C33 C34 C29 0.1(3) . . . . ?
C30 C29 C34 C33 -0.4(3) . . . . ?
C4 C29 C34 C33 -177.73(18) . . . . ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_H2PPPO
_database_code_depnum_ccdc_archive 'CCDC 2095822'
loop_
_audit_author_name
_audit_author_address
'Darina Nasyrova'
;N D Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-07-12 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_RINTA01_H2PPPO              
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: All studied crystals were weak, small and of very poor crystal 
 quality. Morevover, they might contain several minor unidentified domains. 
;
_vrf_PLAT020_H2PPPO              
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.203 Report
RESPONSE: All studied crystals were weak, small and of very poor crystal 
 quality. Morevover, they might contain several minor unidentified domains. 
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H27 O P'
_chemical_formula_sum            'C34 H27 O P'
_chemical_formula_weight         482.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           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                   11.6191(6)
_cell_length_b                   5.9902(4)
_cell_length_c                   35.856(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.762(4)
_cell_angle_gamma                90
_cell_volume                     2495.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2825
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      21.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6140
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            45348
_diffrn_reflns_av_unetI/netI     0.1195
_diffrn_reflns_av_R_equivalents  0.2032
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.076
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_full        25.242
_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             5191
_reflns_number_gt                2721
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+9.7185P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5191
_refine_ls_number_parameters     325
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1758
_refine_ls_R_factor_gt           0.0879
_refine_ls_wR_factor_ref         0.2302
_refine_ls_wR_factor_gt          0.1826
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.044
_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 0.31272(11) 0.1410(3) 0.66233(4) 0.0316(4) Uani 1 1 d . . . . .
O1 O 0.3655(3) -0.0833(6) 0.65726(10) 0.0368(10) Uani 1 1 d . . . . .
C1 C 0.1699(4) 0.1357(9) 0.64526(12) 0.0262(11) Uani 1 1 d . U . . .
H1 H 0.142581 -0.022595 0.645163 0.031 Uiso 1 1 calc R U . . .
C2 C 0.1811(4) 0.2141(9) 0.60443(13) 0.0277(12) Uani 1 1 d . . . . .
C3 C 0.2789(4) 0.3248(9) 0.59697(12) 0.0255(12) Uani 1 1 d . . . . .
C4 C 0.3621(4) 0.3589(10) 0.63024(13) 0.0274(12) Uani 1 1 d . . . . .
H4 H 0.345839 0.507759 0.641647 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3275(4) 0.2404(10) 0.70937(14) 0.0285(12) Uani 1 1 d . . . . .
C6 C 0.2965(4) 0.4530(10) 0.72121(14) 0.0324(13) Uani 1 1 d . . . . .
H6 H 0.265199 0.557689 0.703956 0.039 Uiso 1 1 calc R U . . .
C7 C 0.3119(4) 0.5110(10) 0.75852(14) 0.0328(13) Uani 1 1 d . . . . .
H7 H 0.290297 0.655774 0.766701 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3579(4) 0.3613(11) 0.78373(14) 0.0329(13) Uani 1 1 d . . . . .
H8 H 0.368177 0.402256 0.809154 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3887(4) 0.1521(10) 0.77181(13) 0.0307(13) Uani 1 1 d . . . . .
H9 H 0.420335 0.048741 0.789227 0.037 Uiso 1 1 calc R U . . .
C10 C 0.3746(4) 0.0889(10) 0.73490(14) 0.0312(13) Uani 1 1 d . . . . .
H10 H 0.396832 -0.056072 0.727019 0.037 Uiso 1 1 calc R U . . .
C11 C 0.0787(4) 0.2827(9) 0.66623(13) 0.0267(12) Uani 1 1 d . . . . .
C12 C 0.0477(4) 0.4931(10) 0.65407(14) 0.0340(14) Uani 1 1 d . . . . .
H12 H 0.081365 0.551507 0.632117 0.041 Uiso 1 1 calc R U . . .
C13 C -0.0316(4) 0.6213(11) 0.67327(15) 0.0376(14) Uani 1 1 d . . . . .
H13 H -0.052386 0.765520 0.664480 0.045 Uiso 1 1 calc R U . . .
C14 C -0.0801(4) 0.5364(12) 0.70538(15) 0.0425(16) Uani 1 1 d . . . . .
H14 H -0.134541 0.622895 0.718626 0.051 Uiso 1 1 calc R U . . .
C15 C -0.0503(4) 0.3301(12) 0.71807(15) 0.0403(16) Uani 1 1 d . . . . .
H15 H -0.083624 0.273896 0.740230 0.048 Uiso 1 1 calc R U . . .
C16 C 0.0292(4) 0.1999(10) 0.69864(14) 0.0352(14) Uani 1 1 d . . . . .
H16 H 0.049428 0.055596 0.707542 0.042 Uiso 1 1 calc R U . . .
C17 C 0.0816(4) 0.1754(9) 0.57836(12) 0.0255(12) Uani 1 1 d . . . . .
C18 C 0.0371(4) 0.3434(10) 0.55573(13) 0.0282(12) Uani 1 1 d . . . . .
H18 H 0.072430 0.486371 0.555740 0.034 Uiso 1 1 calc R U . . .
C19 C -0.0591(4) 0.3042(10) 0.53300(13) 0.0299(13) Uani 1 1 d . . . . .
H19 H -0.088521 0.420416 0.517572 0.036 Uiso 1 1 calc R U . . .
C20 C -0.1116(4) 0.0984(10) 0.53277(14) 0.0321(13) Uani 1 1 d . . . . .
H20 H -0.177206 0.072942 0.517264 0.039 Uiso 1 1 calc R U . . .
C21 C -0.0692(4) -0.0703(10) 0.55496(14) 0.0345(14) Uani 1 1 d . . . . .
H21 H -0.104933 -0.212888 0.554650 0.041 Uiso 1 1 calc R U . . .
C22 C 0.0269(4) -0.0316(10) 0.57804(14) 0.0336(13) Uani 1 1 d . . . . .
H22 H 0.055091 -0.147873 0.593678 0.040 Uiso 1 1 calc R U . . .
C23 C 0.3110(4) 0.4211(9) 0.56057(13) 0.0267(12) Uani 1 1 d . . . . .
C24 C 0.2970(4) 0.3033(11) 0.52729(13) 0.0340(14) Uani 1 1 d . . . . .
H24 H 0.266230 0.156506 0.527955 0.041 Uiso 1 1 calc R U . . .
C25 C 0.3265(4) 0.3937(13) 0.49364(15) 0.0434(17) Uani 1 1 d . . . . .
H25 H 0.315659 0.310280 0.471337 0.052 Uiso 1 1 calc R U . . .
C26 C 0.3721(4) 0.6067(13) 0.49226(16) 0.0476(19) Uani 1 1 d . . . . .
H26 H 0.392875 0.669889 0.468992 0.057 Uiso 1 1 calc R U . . .
C27 C 0.3876(4) 0.7283(11) 0.52496(16) 0.0415(15) Uani 1 1 d . . . . .
H27 H 0.418861 0.874766 0.524150 0.050 Uiso 1 1 calc R U . . .
C28 C 0.3571(4) 0.6342(10) 0.55886(15) 0.0340(13) Uani 1 1 d . . . . .
H28 H 0.368014 0.717289 0.581198 0.041 Uiso 1 1 calc R U . . .
C29 C 0.4899(4) 0.3454(9) 0.62237(12) 0.0249(11) Uani 1 1 d . . . . .
C30 C 0.5619(4) 0.5207(10) 0.63209(14) 0.0318(13) Uani 1 1 d . . . . .
H30 H 0.529785 0.653327 0.642101 0.038 Uiso 1 1 calc R U . . .
C31 C 0.6804(4) 0.5064(10) 0.62747(14) 0.0352(14) Uani 1 1 d . . . . .
H31 H 0.728750 0.627999 0.634317 0.042 Uiso 1 1 calc R U . . .
C32 C 0.7274(4) 0.3126(11) 0.61275(14) 0.0367(15) Uani 1 1 d . . . . .
H32 H 0.808301 0.299946 0.609893 0.044 Uiso 1 1 calc R U . . .
C33 C 0.6557(4) 0.1378(10) 0.60224(13) 0.0340(13) Uani 1 1 d . . . . .
H33 H 0.687501 0.006484 0.591672 0.041 Uiso 1 1 calc R U . . .
C34 C 0.5378(4) 0.1540(10) 0.60709(13) 0.0309(12) Uani 1 1 d . . . . .
H34 H 0.489300 0.033272 0.599911 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.489(4) . ?
P1 C1 1.761(5) . ?
P1 C5 1.795(5) . ?
P1 C4 1.837(5) . ?
C1 C2 1.544(6) . ?
C1 C11 1.576(7) . ?
C1 H1 1.0000 . ?
C2 C3 1.346(7) . ?
C2 C17 1.495(6) . ?
C3 C23 1.479(7) . ?
C3 C4 1.539(6) . ?
C4 C29 1.516(6) . ?
C4 H4 1.0000 . ?
C5 C6 1.391(8) . ?
C5 C10 1.396(7) . ?
C6 C7 1.392(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.376(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.380(8) . ?
C11 C16 1.394(7) . ?
C12 C13 1.390(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.360(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.402(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.389(7) . ?
C17 C22 1.393(8) . ?
C18 C19 1.394(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.376(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.400(7) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.386(8) . ?
C23 C24 1.394(7) . ?
C24 C25 1.370(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(9) . ?
C25 H25 0.9500 . ?
C26 C27 1.390(9) . ?
C26 H26 0.9500 . ?
C27 C28 1.390(7) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.384(7) . ?
C29 C34 1.390(7) . ?
C30 C31 1.392(7) . ?
C30 H30 0.9500 . ?
C31 C32 1.390(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.387(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.387(7) . ?
C33 H33 0.9500 . ?
C34 H34 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
O1 P1 C1 109.2(2) . . ?
O1 P1 C5 112.3(2) . . ?
C1 P1 C5 114.2(2) . . ?
O1 P1 C4 115.6(2) . . ?
C1 P1 C4 95.5(2) . . ?
C5 P1 C4 109.0(3) . . ?
C2 C1 C11 110.4(4) . . ?
C2 C1 P1 103.5(3) . . ?
C11 C1 P1 117.4(3) . . ?
C2 C1 H1 108.4 . . ?
C11 C1 H1 108.4 . . ?
P1 C1 H1 108.4 . . ?
C3 C2 C17 126.9(5) . . ?
C3 C2 C1 114.9(4) . . ?
C17 C2 C1 118.1(4) . . ?
C2 C3 C23 126.2(4) . . ?
C2 C3 C4 115.8(4) . . ?
C23 C3 C4 118.0(4) . . ?
C29 C4 C3 117.1(4) . . ?
C29 C4 P1 113.2(4) . . ?
C3 C4 P1 101.1(3) . . ?
C29 C4 H4 108.3 . . ?
C3 C4 H4 108.3 . . ?
P1 C4 H4 108.3 . . ?
C6 C5 C10 119.7(5) . . ?
C6 C5 P1 124.6(4) . . ?
C10 C5 P1 115.6(4) . . ?
C5 C6 C7 119.5(5) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.8(5) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 119.4(5) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 121.3(5) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C5 119.3(6) . . ?
C9 C10 H10 120.3 . . ?
C5 C10 H10 120.3 . . ?
C12 C11 C16 118.7(5) . . ?
C12 C11 C1 122.2(5) . . ?
C16 C11 C1 119.1(5) . . ?
C11 C12 C13 121.3(5) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 119.3(6) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 120.5(6) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.4(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 119.9(6) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C22 118.3(4) . . ?
C18 C17 C2 122.1(5) . . ?
C22 C17 C2 119.5(5) . . ?
C17 C18 C19 120.6(5) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 120.4(5) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.0(5) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 119.8(5) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C17 C22 C21 120.8(5) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C28 C23 C24 118.0(5) . . ?
C28 C23 C3 120.0(5) . . ?
C24 C23 C3 122.0(5) . . ?
C25 C24 C23 121.8(6) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C24 C25 C26 119.8(6) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C27 119.9(5) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C28 119.6(6) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C23 C28 C27 121.0(6) . . ?
C23 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C30 C29 C34 118.7(4) . . ?
C30 C29 C4 120.2(5) . . ?
C34 C29 C4 121.0(5) . . ?
C29 C30 C31 121.3(5) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C32 C31 C30 119.4(5) . . ?
C32 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
C33 C32 C31 119.7(5) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C34 C33 C32 120.3(5) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C29 120.6(5) . . ?
C33 C34 H34 119.7 . . ?
C29 C34 H34 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 C1 C2 -92.6(4) . . . . ?
C5 P1 C1 C2 140.7(3) . . . . ?
C4 P1 C1 C2 26.9(4) . . . . ?
O1 P1 C1 C11 145.5(4) . . . . ?
C5 P1 C1 C11 18.8(5) . . . . ?
C4 P1 C1 C11 -94.9(4) . . . . ?
C11 C1 C2 C3 107.0(5) . . . . ?
P1 C1 C2 C3 -19.5(6) . . . . ?
C11 C1 C2 C17 -68.9(6) . . . . ?
P1 C1 C2 C17 164.7(4) . . . . ?
C17 C2 C3 C23 -3.6(9) . . . . ?
C1 C2 C3 C23 -179.0(5) . . . . ?
C17 C2 C3 C4 174.3(5) . . . . ?
C1 C2 C3 C4 -1.1(7) . . . . ?
C2 C3 C4 C29 143.4(5) . . . . ?
C23 C3 C4 C29 -38.5(7) . . . . ?
C2 C3 C4 P1 20.0(5) . . . . ?
C23 C3 C4 P1 -161.9(4) . . . . ?
O1 P1 C4 C29 -38.8(4) . . . . ?
C1 P1 C4 C29 -153.1(4) . . . . ?
C5 P1 C4 C29 88.8(4) . . . . ?
O1 P1 C4 C3 87.3(3) . . . . ?
C1 P1 C4 C3 -27.1(4) . . . . ?
C5 P1 C4 C3 -145.1(3) . . . . ?
O1 P1 C5 C6 173.4(4) . . . . ?
C1 P1 C5 C6 -61.6(5) . . . . ?
C4 P1 C5 C6 43.9(5) . . . . ?
O1 P1 C5 C10 -6.1(5) . . . . ?
C1 P1 C5 C10 119.0(4) . . . . ?
C4 P1 C5 C10 -135.6(4) . . . . ?
C10 C5 C6 C7 -0.7(7) . . . . ?
P1 C5 C6 C7 179.9(4) . . . . ?
C5 C6 C7 C8 0.4(8) . . . . ?
C6 C7 C8 C9 -0.1(8) . . . . ?
C7 C8 C9 C10 0.1(7) . . . . ?
C8 C9 C10 C5 -0.4(7) . . . . ?
C6 C5 C10 C9 0.7(7) . . . . ?
P1 C5 C10 C9 -179.8(4) . . . . ?
C2 C1 C11 C12 -21.4(6) . . . . ?
P1 C1 C11 C12 96.8(5) . . . . ?
C2 C1 C11 C16 160.0(4) . . . . ?
P1 C1 C11 C16 -81.8(5) . . . . ?
C16 C11 C12 C13 -0.5(7) . . . . ?
C1 C11 C12 C13 -179.0(4) . . . . ?
C11 C12 C13 C14 0.3(8) . . . . ?
C12 C13 C14 C15 0.1(8) . . . . ?
C13 C14 C15 C16 -0.5(8) . . . . ?
C12 C11 C16 C15 0.1(7) . . . . ?
C1 C11 C16 C15 178.7(4) . . . . ?
C14 C15 C16 C11 0.4(8) . . . . ?
C3 C2 C17 C18 -44.4(8) . . . . ?
C1 C2 C17 C18 130.8(5) . . . . ?
C3 C2 C17 C22 139.3(6) . . . . ?
C1 C2 C17 C22 -45.4(7) . . . . ?
C22 C17 C18 C19 -0.8(7) . . . . ?
C2 C17 C18 C19 -177.1(4) . . . . ?
C17 C18 C19 C20 0.3(7) . . . . ?
C18 C19 C20 C21 -0.2(8) . . . . ?
C19 C20 C21 C22 0.6(8) . . . . ?
C18 C17 C22 C21 1.2(8) . . . . ?
C2 C17 C22 C21 177.6(5) . . . . ?
C20 C21 C22 C17 -1.1(8) . . . . ?
C2 C3 C23 C28 135.1(6) . . . . ?
C4 C3 C23 C28 -42.7(6) . . . . ?
C2 C3 C23 C24 -45.3(8) . . . . ?
C4 C3 C23 C24 136.9(5) . . . . ?
C28 C23 C24 C25 -0.6(7) . . . . ?
C3 C23 C24 C25 179.8(4) . . . . ?
C23 C24 C25 C26 0.4(8) . . . . ?
C24 C25 C26 C27 -0.1(8) . . . . ?
C25 C26 C27 C28 0.1(8) . . . . ?
C24 C23 C28 C27 0.5(7) . . . . ?
C3 C23 C28 C27 -179.9(4) . . . . ?
C26 C27 C28 C23 -0.3(7) . . . . ?
C3 C4 C29 C30 124.7(5) . . . . ?
P1 C4 C29 C30 -118.3(5) . . . . ?
C3 C4 C29 C34 -58.5(7) . . . . ?
P1 C4 C29 C34 58.5(5) . . . . ?
C34 C29 C30 C31 -1.2(7) . . . . ?
C4 C29 C30 C31 175.6(5) . . . . ?
C29 C30 C31 C32 0.1(8) . . . . ?
C30 C31 C32 C33 1.2(8) . . . . ?
C31 C32 C33 C34 -1.3(8) . . . . ?
C32 C33 C34 C29 0.3(8) . . . . ?
C30 C29 C34 C33 1.0(7) . . . . ?
C4 C29 C34 C33 -175.8(4) . . . . ?

_refine_diff_density_max         0.829
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.079

