# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_20118
_audit_block_doi                 10.5517/ccdc.csd.cc29kqsd
_database_code_depnum_ccdc_archive 'CCDC 2132204'
loop_
_audit_author_name
_audit_author_address
'Maren Pink'
;Indiana university
United States of America
;
_audit_update_record             
;
2022-01-03 deposited with the CCDC.	2022-05-03 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         ?
_chemical_formula_sum            'C31 H33 O3 P'
_chemical_formula_weight         484.54

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                   12.9448(4)
_cell_length_b                   16.4183(5)
_cell_length_c                   13.3984(4)
_cell_angle_alpha                90
_cell_angle_beta                 118.1820(10)
_cell_angle_gamma                90
_cell_volume                     2510.01(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      28.21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.142
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7259
_exptl_absorpt_correction_T_max  0.7436
_exptl_absorpt_process_details   
;
L. Krause, R. Herbst-Irmer, G.M. Sheldrick, D. Stalke,
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination"
J. Appl. Cryst. (2015), 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_details      
'0.50 degree frames measured for 5 and 9 seconds each'
_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            154694
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.124
_diffrn_reflns_theta_max         28.320
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6236
_reflns_number_gt                5155
_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       'BIS v6.2.9 (BrukerNano, 2018)'
_computing_cell_refinement       'SAINT V8.38A (BrukerNano, 2017)'
_computing_data_reduction        'SAINT V8.38A (BrukerNano, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 v2018.1-0 (BrukerNano, 2018)'

_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)+(0.0358P)²+1.3698P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_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         6236
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.035
_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
P1 P 0.25469(3) 0.48044(2) 0.45015(3) 0.01723(8) Uani 1 1 d . . . . .
O1 O 0.34249(9) 0.57243(6) 0.75562(8) 0.0277(2) Uani 1 1 d . . . . .
O2 O 0.34023(8) 0.45611(6) 0.41210(8) 0.0237(2) Uani 1 1 d . . . . .
O3 O 0.25096(8) 0.42665(5) 0.54693(7) 0.01954(19) Uani 1 1 d . . . . .
C1 C 0.59873(11) 0.46596(8) 0.78225(11) 0.0218(3) Uani 1 1 d . . . . .
H1 H 0.610145 0.492213 0.725026 0.026 Uiso 1 1 calc R U . . .
C2 C 0.67829(12) 0.40764(9) 0.85149(12) 0.0276(3) Uani 1 1 d . . . . .
H2 H 0.745314 0.395206 0.842859 0.033 Uiso 1 1 calc R U . . .
C3 C 0.66020(14) 0.36759(9) 0.93302(12) 0.0319(3) Uani 1 1 d . . . . .
H3 H 0.713680 0.326763 0.978656 0.038 Uiso 1 1 calc R U . . .
C4 C 0.56407(14) 0.38701(10) 0.94814(12) 0.0332(3) Uani 1 1 d . . . . .
H4 H 0.552080 0.359792 1.004398 0.040 Uiso 1 1 calc R U . . .
C5 C 0.48603(13) 0.44591(9) 0.88125(11) 0.0265(3) Uani 1 1 d . . . . .
H5 H 0.420839 0.459600 0.892296 0.032 Uiso 1 1 calc R U . . .
C6 C 0.50224(11) 0.48568(8) 0.79719(10) 0.0195(2) Uani 1 1 d . . . . .
C7 C 0.41337(11) 0.54733(8) 0.72690(11) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.40900(11) 0.58091(8) 0.61898(11) 0.0213(3) Uani 1 1 d . . . . .
H8A H 0.460153 0.547859 0.598487 0.026 Uiso 1 1 calc R U . . .
H8AB H 0.438525 0.637604 0.631990 0.026 Uiso 1 1 calc R U . . .
C9 C 0.28196(11) 0.57907(7) 0.52078(10) 0.0184(2) Uani 1 1 d . . . . .
H9 H 0.228142 0.583813 0.554849 0.022 Uiso 1 1 calc R U . . .
C10 C 0.25258(11) 0.64778(7) 0.43629(10) 0.0192(2) Uani 1 1 d . . . . .
C11 C 0.32910(12) 0.67145(8) 0.39605(12) 0.0241(3) Uani 1 1 d . . . . .
H11 H 0.401751 0.643950 0.421213 0.029 Uiso 1 1 calc R U . . .
C12 C 0.29993(14) 0.73517(8) 0.31914(12) 0.0287(3) Uani 1 1 d . . . . .
H12 H 0.353163 0.751136 0.292541 0.034 Uiso 1 1 calc R U . . .
C13 C 0.19418(14) 0.77561(9) 0.28091(12) 0.0300(3) Uani 1 1 d . . . . .
H13 H 0.174619 0.819010 0.228151 0.036 Uiso 1 1 calc R U . . .
C14 C 0.11709(13) 0.75219(9) 0.32032(12) 0.0294(3) Uani 1 1 d . . . . .
H14 H 0.044247 0.779560 0.294443 0.035 Uiso 1 1 calc R U . . .
C15 C 0.14609(12) 0.68886(8) 0.39748(12) 0.0248(3) Uani 1 1 d . . . . .
H15 H 0.092835 0.673250 0.424220 0.030 Uiso 1 1 calc R U . . .
C16 C 0.10731(11) 0.48350(7) 0.33567(11) 0.0188(2) Uani 1 1 d . . . . .
C17 C 0.01370(12) 0.49676(9) 0.35778(13) 0.0261(3) Uani 1 1 d . . . . .
H17 H 0.028223 0.505294 0.433438 0.031 Uiso 1 1 calc R U . . .
C18 C -0.10039(13) 0.49758(9) 0.27029(14) 0.0323(3) Uani 1 1 d . . . . .
H18 H -0.163846 0.506842 0.285811 0.039 Uiso 1 1 calc R U . . .
C19 C -0.12133(13) 0.48489(9) 0.16051(14) 0.0351(4) Uani 1 1 d . . . . .
H19 H -0.199568 0.484761 0.100553 0.042 Uiso 1 1 calc R U . . .
C20 C -0.02976(15) 0.47240(10) 0.13718(13) 0.0354(4) Uani 1 1 d . . . . .
H20 H -0.045041 0.463968 0.061277 0.043 Uiso 1 1 calc R U . . .
C21 C 0.08542(13) 0.47210(8) 0.22465(11) 0.0259(3) Uani 1 1 d . . . . .
H21 H 0.148614 0.464123 0.208369 0.031 Uiso 1 1 calc R U . . .
C22 C 0.24805(11) 0.33716(7) 0.55123(10) 0.0175(2) Uani 1 1 d . . . . .
C23 C 0.37313(11) 0.30465(8) 0.60391(12) 0.0236(3) Uani 1 1 d . . . . .
H23A H 0.421185 0.330343 0.678689 0.028 Uiso 1 1 calc R U . . .
H23B H 0.408655 0.317715 0.554635 0.028 Uiso 1 1 calc R U . . .
C24 C 0.36986(12) 0.21180(8) 0.61755(13) 0.0275(3) Uani 1 1 d . . . . .
H24 H 0.451519 0.189762 0.652419 0.033 Uiso 1 1 calc R U . . .
C25 C 0.31532(13) 0.19237(9) 0.69434(12) 0.0300(3) Uani 1 1 d . . . . .
H25A H 0.314684 0.132714 0.704817 0.036 Uiso 1 1 calc R U . . .
H25B H 0.362457 0.217670 0.769577 0.036 Uiso 1 1 calc R U . . .
C26 C 0.18993(13) 0.22532(8) 0.64039(12) 0.0275(3) Uani 1 1 d . . . . .
H26 H 0.153912 0.212453 0.690144 0.033 Uiso 1 1 calc R U . . .
C27 C 0.11734(13) 0.18632(9) 0.52416(13) 0.0304(3) Uani 1 1 d . . . . .
H27A H 0.114907 0.126540 0.532474 0.036 Uiso 1 1 calc R U . . .
H27B H 0.035991 0.207193 0.489622 0.036 Uiso 1 1 calc R U . . .
C28 C 0.17174(13) 0.20631(8) 0.44771(12) 0.0272(3) Uani 1 1 d . . . . .
H28 H 0.123930 0.180928 0.371627 0.033 Uiso 1 1 calc R U . . .
C29 C 0.17440(12) 0.29945(8) 0.43474(11) 0.0228(3) Uani 1 1 d . . . . .
H29A H 0.208637 0.312994 0.384527 0.027 Uiso 1 1 calc R U . . .
H29B H 0.093693 0.321500 0.400336 0.027 Uiso 1 1 calc R U . . .
C30 C 0.19350(12) 0.31820(8) 0.62719(12) 0.0233(3) Uani 1 1 d . . . . .
H30A H 0.113056 0.340663 0.593485 0.028 Uiso 1 1 calc R U . . .
H30B H 0.240342 0.343697 0.702348 0.028 Uiso 1 1 calc R U . . .
C31 C 0.29691(13) 0.17281(8) 0.50096(13) 0.0306(3) Uani 1 1 d . . . . .
H31A H 0.332487 0.185190 0.451534 0.037 Uiso 1 1 calc R U . . .
H31B H 0.295595 0.112924 0.508926 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 O2 1.4761(9) . ?
P1 O3 1.5883(9) . ?
P1 C16 1.7975(13) . ?
P1 C9 1.8240(13) . ?
O1 C7 1.2221(16) . ?
O3 C22 1.4716(14) . ?
C1 C2 1.3912(19) . ?
C1 C6 1.3933(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4007(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4870(18) . ?
C7 C8 1.5233(18) . ?
C8 C9 1.5469(17) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.5141(17) . ?
C9 H9 1.0000 . ?
C10 C11 1.3881(18) . ?
C10 C15 1.3959(18) . ?
C11 C12 1.3898(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3873(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.3892(18) . ?
C16 C17 1.3937(18) . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.377(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C30 1.5199(17) . ?
C22 C29 1.5241(17) . ?
C22 C23 1.5250(17) . ?
C23 C24 1.5383(18) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.531(2) . ?
C24 C31 1.532(2) . ?
C24 H24 1.0000 . ?
C25 C26 1.530(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.528(2) . ?
C26 C30 1.5383(18) . ?
C26 H26 1.0000 . ?
C27 C28 1.528(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C31 1.531(2) . ?
C28 C29 1.5413(18) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O3 116.64(5) . . ?
O2 P1 C16 112.33(6) . . ?
O3 P1 C16 106.44(5) . . ?
O2 P1 C9 115.25(6) . . ?
O3 P1 C9 98.22(5) . . ?
C16 P1 C9 106.58(6) . . ?
C22 O3 P1 126.75(8) . . ?
C2 C1 C6 119.72(13) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C2 C1 120.30(14) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.15(13) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.85(14) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.48(14) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.47(12) . . ?
C1 C6 C7 123.03(12) . . ?
C5 C6 C7 117.50(12) . . ?
O1 C7 C6 120.09(12) . . ?
O1 C7 C8 118.68(12) . . ?
C6 C7 C8 121.22(11) . . ?
C7 C8 C9 110.39(10) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8AB 109.6 . . ?
C9 C8 H8AB 109.6 . . ?
H8A C8 H8AB 108.1 . . ?
C10 C9 C8 114.34(10) . . ?
C10 C9 P1 110.78(9) . . ?
C8 C9 P1 109.04(9) . . ?
C10 C9 H9 107.5 . . ?
C8 C9 H9 107.5 . . ?
P1 C9 H9 107.5 . . ?
C11 C10 C15 118.71(12) . . ?
C11 C10 C9 121.71(11) . . ?
C15 C10 C9 119.57(12) . . ?
C10 C11 C12 120.32(13) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.70(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.37(13) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 120.12(13) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.78(13) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C21 C16 C17 119.37(12) . . ?
C21 C16 P1 120.49(10) . . ?
C17 C16 P1 120.13(10) . . ?
C18 C17 C16 120.53(14) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.65(14) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 120.52(14) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 120.20(14) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 119.71(14) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
O3 C22 C30 105.03(10) . . ?
O3 C22 C29 112.38(10) . . ?
C30 C22 C29 109.81(11) . . ?
O3 C22 C23 109.05(10) . . ?
C30 C22 C23 110.24(11) . . ?
C29 C22 C23 110.22(11) . . ?
C22 C23 C24 108.61(11) . . ?
C22 C23 H23A 110.0 . . ?
C24 C23 H23A 110.0 . . ?
C22 C23 H23B 110.0 . . ?
C24 C23 H23B 110.0 . . ?
H23A C23 H23B 108.3 . . ?
C25 C24 C31 109.89(12) . . ?
C25 C24 C23 109.48(12) . . ?
C31 C24 C23 109.34(12) . . ?
C25 C24 H24 109.4 . . ?
C31 C24 H24 109.4 . . ?
C23 C24 H24 109.4 . . ?
C26 C25 C24 109.37(11) . . ?
C26 C25 H25A 109.8 . . ?
C24 C25 H25A 109.8 . . ?
C26 C25 H25B 109.8 . . ?
C24 C25 H25B 109.8 . . ?
H25A C25 H25B 108.2 . . ?
C27 C26 C25 109.74(12) . . ?
C27 C26 C30 109.61(11) . . ?
C25 C26 C30 108.79(12) . . ?
C27 C26 H26 109.6 . . ?
C25 C26 H26 109.6 . . ?
C30 C26 H26 109.6 . . ?
C28 C27 C26 109.68(11) . . ?
C28 C27 H27A 109.7 . . ?
C26 C27 H27A 109.7 . . ?
C28 C27 H27B 109.7 . . ?
C26 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
C27 C28 C31 109.38(12) . . ?
C27 C28 C29 109.31(12) . . ?
C31 C28 C29 109.50(12) . . ?
C27 C28 H28 109.5 . . ?
C31 C28 H28 109.5 . . ?
C29 C28 H28 109.5 . . ?
C22 C29 C28 108.91(11) . . ?
C22 C29 H29A 109.9 . . ?
C28 C29 H29A 109.9 . . ?
C22 C29 H29B 109.9 . . ?
C28 C29 H29B 109.9 . . ?
H29A C29 H29B 108.3 . . ?
C22 C30 C26 109.19(11) . . ?
C22 C30 H30A 109.8 . . ?
C26 C30 H30A 109.8 . . ?
C22 C30 H30B 109.8 . . ?
C26 C30 H30B 109.8 . . ?
H30A C30 H30B 108.3 . . ?
C28 C31 C24 109.39(11) . . ?
C28 C31 H31A 109.8 . . ?
C24 C31 H31A 109.8 . . ?
C28 C31 H31B 109.8 . . ?
C24 C31 H31B 109.8 . . ?
H31A C31 H31B 108.2 . . ?

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
O2 P1 O3 C22 -47.08(11) . . . . ?
C16 P1 O3 C22 79.16(10) . . . . ?
C9 P1 O3 C22 -170.77(10) . . . . ?
C6 C1 C2 C3 1.8(2) . . . . ?
C1 C2 C3 C4 -1.7(2) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C2 C1 C6 C5 -0.57(19) . . . . ?
C2 C1 C6 C7 179.93(12) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C4 C5 C6 C7 178.84(13) . . . . ?
C1 C6 C7 O1 -167.33(12) . . . . ?
C5 C6 C7 O1 13.15(18) . . . . ?
C1 C6 C7 C8 12.20(18) . . . . ?
C5 C6 C7 C8 -167.32(12) . . . . ?
O1 C7 C8 C9 -48.26(16) . . . . ?
C6 C7 C8 C9 132.21(12) . . . . ?
C7 C8 C9 C10 147.40(11) . . . . ?
C7 C8 C9 P1 -87.99(11) . . . . ?
O2 P1 C9 C10 73.27(10) . . . . ?
O3 P1 C9 C10 -162.05(9) . . . . ?
C16 P1 C9 C10 -52.09(10) . . . . ?
O2 P1 C9 C8 -53.41(10) . . . . ?
O3 P1 C9 C8 71.28(9) . . . . ?
C16 P1 C9 C8 -178.76(8) . . . . ?
C8 C9 C10 C11 43.88(17) . . . . ?
P1 C9 C10 C11 -79.80(13) . . . . ?
C8 C9 C10 C15 -136.02(12) . . . . ?
P1 C9 C10 C15 100.30(12) . . . . ?
C15 C10 C11 C12 0.38(19) . . . . ?
C9 C10 C11 C12 -179.52(12) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C13 C14 C15 C10 -0.1(2) . . . . ?
C11 C10 C15 C14 -0.1(2) . . . . ?
C9 C10 C15 C14 179.81(12) . . . . ?
O2 P1 C16 C21 -6.37(12) . . . . ?
O3 P1 C16 C21 -135.18(10) . . . . ?
C9 P1 C16 C21 120.74(11) . . . . ?
O2 P1 C16 C17 173.13(10) . . . . ?
O3 P1 C16 C17 44.33(12) . . . . ?
C9 P1 C16 C17 -59.76(12) . . . . ?
C21 C16 C17 C18 0.8(2) . . . . ?
P1 C16 C17 C18 -178.70(11) . . . . ?
C16 C17 C18 C19 0.2(2) . . . . ?
C17 C18 C19 C20 -0.8(2) . . . . ?
C18 C19 C20 C21 0.3(2) . . . . ?
C17 C16 C21 C20 -1.3(2) . . . . ?
P1 C16 C21 C20 178.21(11) . . . . ?
C19 C20 C21 C16 0.8(2) . . . . ?
P1 O3 C22 C30 -156.23(9) . . . . ?
P1 O3 C22 C29 -36.89(14) . . . . ?
P1 O3 C22 C23 85.63(12) . . . . ?
O3 C22 C23 C24 175.13(10) . . . . ?
C30 C22 C23 C24 60.31(14) . . . . ?
C29 C22 C23 C24 -61.07(14) . . . . ?
C22 C23 C24 C25 -59.89(14) . . . . ?
C22 C23 C24 C31 60.55(15) . . . . ?
C31 C24 C25 C26 -59.35(15) . . . . ?
C23 C24 C25 C26 60.75(15) . . . . ?
C24 C25 C26 C27 59.35(14) . . . . ?
C24 C25 C26 C30 -60.56(15) . . . . ?
C25 C26 C27 C28 -60.00(14) . . . . ?
C30 C26 C27 C28 59.41(15) . . . . ?
C26 C27 C28 C31 60.15(15) . . . . ?
C26 C27 C28 C29 -59.73(15) . . . . ?
O3 C22 C29 C28 -177.57(10) . . . . ?
C30 C22 C29 C28 -61.06(14) . . . . ?
C23 C22 C29 C28 60.57(14) . . . . ?
C27 C28 C29 C22 60.25(14) . . . . ?
C31 C28 C29 C22 -59.55(15) . . . . ?
O3 C22 C30 C26 -178.24(10) . . . . ?
C29 C22 C30 C26 60.72(14) . . . . ?
C23 C22 C30 C26 -60.90(14) . . . . ?
C27 C26 C30 C22 -59.59(15) . . . . ?
C25 C26 C30 C22 60.40(15) . . . . ?
C27 C28 C31 C24 -59.88(15) . . . . ?
C29 C28 C31 C24 59.88(15) . . . . ?
C25 C24 C31 C28 59.73(15) . . . . ?
C23 C24 C31 C28 -60.46(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H8A O2 0.99 2.65 3.5153(16) 145.5 3_666 yes

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.044



_exptl_crystal_recrystallization_method 'vapor diffusion'
