# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2024

####################################################################### 
# 
# 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_ar230510P1
_database_code_depnum_ccdc_archive 'CCDC 2277412'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2023-08-11 deposited with the CCDC.	2023-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 O3 P'
_chemical_formula_sum            'C16 H21 O3 P'
_chemical_formula_weight         292.30

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      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                   9.9495(2)
_cell_length_b                   11.5590(2)
_cell_length_c                   26.1562(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3008.13(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    64670
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.587
_exptl_crystal_size_mid          0.442
_exptl_crystal_size_min          0.372
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6693
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.897
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            64670
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.190
_diffrn_reflns_theta_max         28.287
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7451
_reflns_number_gt                7235
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.992

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

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX4 v2021.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+0.3249P] 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 3121 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(12)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         7451
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0686
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.29042(4) 0.20835(3) 0.84089(2) 0.02781(9) Uani 1 1 d . . . . .
P1A P 0.11983(4) 0.50189(3) 0.56583(2) 0.02481(8) Uani 1 1 d . . . . .
O1 O 0.29198(17) 0.28192(11) 0.88655(5) 0.0450(3) Uani 1 1 d . . . . .
O2 O 0.22006(11) 0.08568(9) 0.84670(4) 0.0257(2) Uani 1 1 d . . . . .
O1A O 0.02777(13) 0.41842(11) 0.58942(5) 0.0371(3) Uani 1 1 d . . . . .
O3 O 0.43175(11) 0.16110(10) 0.82143(5) 0.0329(2) Uani 1 1 d . . . . .
O2A O 0.21915(11) 0.56687(8) 0.60401(4) 0.0245(2) Uani 1 1 d . . . . .
O3A O 0.05380(11) 0.61311(10) 0.54086(4) 0.0302(2) Uani 1 1 d . . . . .
C1 C 0.32016(14) -0.00275(13) 0.86115(5) 0.0240(3) Uani 1 1 d . . . . .
C8A C 0.37216(16) 0.75284(14) 0.56048(6) 0.0307(3) Uani 1 1 d . . . . .
H8AA H 0.469372 0.771092 0.560220 0.037 Uiso 1 1 calc R U . . .
H8AB H 0.353044 0.680487 0.541575 0.037 Uiso 1 1 calc R U . . .
C10 C 0.3415(2) -0.32452(15) 0.81935(8) 0.0450(4) Uani 1 1 d . . . . .
H10A H 0.304875 -0.358249 0.850781 0.067 Uiso 1 1 calc R U . . .
H10B H 0.414193 -0.373661 0.806420 0.067 Uiso 1 1 calc R U . . .
H10C H 0.270251 -0.319129 0.793588 0.067 Uiso 1 1 calc R U . . .
C2 C 0.45613(15) 0.04229(14) 0.83828(7) 0.0304(3) Uani 1 1 d . . . . .
H2 H 0.525108 0.043530 0.866087 0.037 Uiso 1 1 calc R U . . .
C1A C 0.17854(14) 0.68790(11) 0.61359(5) 0.0213(3) Uani 1 1 d . . . . .
C3 C 0.5121(2) -0.02803(17) 0.79288(8) 0.0458(5) Uani 1 1 d . . . . .
H3A H 0.514217 0.021984 0.762163 0.055 Uiso 1 1 calc R U . . .
H3B H 0.605712 -0.051242 0.800636 0.055 Uiso 1 1 calc R U . . .
C2A C 0.08433(14) 0.72053(12) 0.56774(5) 0.0246(3) Uani 1 1 d . . . . .
H2A H -0.001290 0.752739 0.581825 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4302(2) -0.13561(16) 0.78107(7) 0.0393(4) Uani 1 1 d . . . . .
H4 H 0.464389 -0.183734 0.752078 0.047 Uiso 1 1 calc R U . . .
C3A C 0.14354(17) 0.80876(14) 0.52964(6) 0.0314(3) Uani 1 1 d . . . . .
H3AA H 0.151943 0.771494 0.495714 0.038 Uiso 1 1 calc R U . . .
H3AB H 0.080302 0.874406 0.526148 0.038 Uiso 1 1 calc R U . . .
C5 C 0.39644(17) -0.20334(14) 0.83073(6) 0.0314(3) Uani 1 1 d . . . . .
C4A C 0.28084(18) 0.85534(14) 0.54564(6) 0.0312(3) Uani 1 1 d . . . . .
H4A H 0.321828 0.912843 0.521706 0.037 Uiso 1 1 calc R U . . .
C6 C 0.27669(15) -0.11537(12) 0.83660(6) 0.0254(3) Uani 1 1 d . . . . .
H6 H 0.191651 -0.149165 0.850467 0.030 Uiso 1 1 calc R U . . .
C5A C 0.28073(17) 0.89113(13) 0.60315(6) 0.0280(3) Uani 1 1 d . . . . .
C7 C 0.3198(2) -0.00799(16) 0.91928(6) 0.0374(4) Uani 1 1 d . . . . .
H7A H 0.381635 -0.068673 0.930762 0.056 Uiso 1 1 calc R U . . .
H7B H 0.228848 -0.025423 0.931397 0.056 Uiso 1 1 calc R U . . .
H7C H 0.348780 0.066752 0.933119 0.056 Uiso 1 1 calc R U . . .
C6A C 0.30627(14) 0.75910(12) 0.61402(5) 0.0233(3) Uani 1 1 d . . . . .
H6A H 0.368287 0.742760 0.643224 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2809(2) -0.10172(16) 0.77778(6) 0.0361(4) Uani 1 1 d . . . . .
H8A H 0.224338 -0.157983 0.759048 0.043 Uiso 1 1 calc R U . . .
H8B H 0.265073 -0.021754 0.765648 0.043 Uiso 1 1 calc R U . . .
C7A C 0.10696(16) 0.68782(13) 0.66477(6) 0.0286(3) Uani 1 1 d . . . . .
H7AA H 0.082565 0.767261 0.674002 0.043 Uiso 1 1 calc R U . . .
H7AB H 0.166597 0.655629 0.690972 0.043 Uiso 1 1 calc R U . . .
H7AC H 0.025449 0.640523 0.662404 0.043 Uiso 1 1 calc R U . . .
C9 C 0.5057(2) -0.21444(18) 0.87120(8) 0.0439(4) Uani 1 1 d . . . . .
H9A H 0.538794 -0.137326 0.880385 0.066 Uiso 1 1 calc R U . . .
H9B H 0.580067 -0.260848 0.857642 0.066 Uiso 1 1 calc R U . . .
H9C H 0.468688 -0.252293 0.901621 0.066 Uiso 1 1 calc R U . . .
C9A C 0.15819(18) 0.95389(14) 0.62412(7) 0.0351(3) Uani 1 1 d . . . . .
H9AA H 0.166109 0.960944 0.661333 0.053 Uiso 1 1 calc R U . . .
H9AB H 0.076899 0.910003 0.615670 0.053 Uiso 1 1 calc R U . . .
H9AC H 0.152617 1.031175 0.608856 0.053 Uiso 1 1 calc R U . . .
C11 C 0.21326(15) 0.27928(13) 0.78810(6) 0.0272(3) Uani 1 1 d . . . . .
C10A C 0.4054(2) 0.96143(16) 0.61745(8) 0.0426(4) Uani 1 1 d . . . . .
H10D H 0.410365 0.969295 0.654708 0.064 Uiso 1 1 calc R U . . .
H10E H 0.399717 1.038343 0.601831 0.064 Uiso 1 1 calc R U . . .
H10F H 0.485999 0.921716 0.604973 0.064 Uiso 1 1 calc R U . . .
C12 C 0.1968(2) 0.22647(15) 0.74061(7) 0.0382(4) Uani 1 1 d . . . . .
H12 H 0.232092 0.151257 0.734790 0.046 Uiso 1 1 calc R U . . .
C11A C 0.22116(16) 0.43542(13) 0.51803(6) 0.0275(3) Uani 1 1 d . . . . .
C13 C 0.1287(2) 0.28381(17) 0.70179(7) 0.0439(4) Uani 1 1 d . . . . .
H13 H 0.117553 0.247708 0.669434 0.053 Uiso 1 1 calc R U . . .
C12A C 0.26225(17) 0.49404(16) 0.47411(6) 0.0336(3) Uani 1 1 d . . . . .
H12A H 0.234229 0.571474 0.468240 0.040 Uiso 1 1 calc R U . . .
C14 C 0.07681(18) 0.39364(16) 0.71011(8) 0.0395(4) Uani 1 1 d . . . . .
H14 H 0.028651 0.431985 0.683720 0.047 Uiso 1 1 calc R U . . .
C13A C 0.3448(2) 0.43794(19) 0.43894(7) 0.0431(4) Uani 1 1 d . . . . .
H13A H 0.372803 0.477545 0.408952 0.052 Uiso 1 1 calc R U . . .
C15 C 0.09518(19) 0.44689(15) 0.75656(7) 0.0388(4) Uani 1 1 d . . . . .
H15 H 0.060723 0.522541 0.762022 0.047 Uiso 1 1 calc R U . . .
C14A C 0.3863(2) 0.32552(19) 0.44713(8) 0.0467(5) Uani 1 1 d . . . . .
H14A H 0.443597 0.288533 0.423117 0.056 Uiso 1 1 calc R U . . .
C16 C 0.16400(18) 0.39062(14) 0.79567(7) 0.0333(3) Uani 1 1 d . . . . .
H16 H 0.177343 0.428276 0.827550 0.040 Uiso 1 1 calc R U . . .
C15A C 0.3445(2) 0.26705(17) 0.49017(8) 0.0468(5) Uani 1 1 d . . . . .
H15A H 0.372789 0.189561 0.495676 0.056 Uiso 1 1 calc R U . . .
C16A C 0.26128(19) 0.32058(15) 0.52548(7) 0.0366(4) Uani 1 1 d . . . . .
H16A H 0.231484 0.279302 0.554774 0.044 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 1.4664(12) . ?
P1 O2 1.5887(11) . ?
P1 O3 1.5920(13) . ?
P1 C11 1.7798(15) . ?
P1A O1A 1.4666(12) . ?
P1A O3A 1.5846(12) . ?
P1A O2A 1.5931(10) . ?
P1A C11A 1.7804(15) . ?
O2 C1 1.4763(17) . ?
O3 C2 1.4627(18) . ?
O2A C1A 1.4776(16) . ?
O3A C2A 1.4589(17) . ?
C1 C6 1.515(2) . ?
C1 C7 1.522(2) . ?
C1 C2 1.568(2) . ?
C8A C4A 1.543(2) . ?
C8A C6A 1.548(2) . ?
C10 C5 1.533(2) . ?
C2 C3 1.543(3) . ?
C1A C6A 1.5141(19) . ?
C1A C7A 1.516(2) . ?
C1A C2A 1.5680(19) . ?
C3 C4 1.518(3) . ?
C2A C3A 1.543(2) . ?
C4 C8 1.539(3) . ?
C4 C5 1.553(2) . ?
C3A C4A 1.527(2) . ?
C5 C9 1.523(2) . ?
C5 C6 1.574(2) . ?
C4A C5A 1.560(2) . ?
C6 C8 1.547(2) . ?
C5A C9A 1.521(2) . ?
C5A C10A 1.529(2) . ?
C5A C6A 1.573(2) . ?
C11 C16 1.391(2) . ?
C11 C12 1.394(2) . ?
C12 C13 1.389(2) . ?
C11A C12A 1.395(2) . ?
C11A C16A 1.400(2) . ?
C13 C14 1.388(3) . ?
C12A C13A 1.393(2) . ?
C14 C15 1.374(3) . ?
C13A C14A 1.380(3) . ?
C15 C16 1.392(2) . ?
C14A C15A 1.377(3) . ?
C15A C16A 1.386(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 116.38(7) . . ?
O1 P1 O3 116.74(8) . . ?
O2 P1 O3 96.52(6) . . ?
O1 P1 C11 111.68(8) . . ?
O2 P1 C11 107.18(7) . . ?
O3 P1 C11 106.92(7) . . ?
O1A P1A O3A 116.63(7) . . ?
O1A P1A O2A 115.71(7) . . ?
O3A P1A O2A 97.65(6) . . ?
O1A P1A C11A 111.42(7) . . ?
O3A P1A C11A 107.18(7) . . ?
O2A P1A C11A 107.01(6) . . ?
C1 O2 P1 110.20(9) . . ?
C2 O3 P1 111.86(10) . . ?
C1A O2A P1A 112.52(8) . . ?
C2A O3A P1A 113.92(9) . . ?
O2 C1 C6 107.10(11) . . ?
O2 C1 C7 106.37(12) . . ?
C6 C1 C7 112.88(13) . . ?
O2 C1 C2 104.75(11) . . ?
C6 C1 C2 111.72(12) . . ?
C7 C1 C2 113.34(13) . . ?
C4A C8A C6A 86.69(11) . . ?
O3 C2 C3 108.81(14) . . ?
O3 C2 C1 106.47(12) . . ?
C3 C2 C1 115.48(13) . . ?
O2A C1A C6A 106.64(11) . . ?
O2A C1A C7A 106.11(11) . . ?
C6A C1A C7A 112.83(12) . . ?
O2A C1A C2A 105.16(11) . . ?
C6A C1A C2A 112.13(11) . . ?
C7A C1A C2A 113.24(12) . . ?
C4 C3 C2 113.21(14) . . ?
O3A C2A C3A 109.31(12) . . ?
O3A C2A C1A 106.76(11) . . ?
C3A C2A C1A 115.13(12) . . ?
C3 C4 C8 108.72(15) . . ?
C3 C4 C5 111.03(16) . . ?
C8 C4 C5 88.06(13) . . ?
C4A C3A C2A 113.44(12) . . ?
C9 C5 C10 108.22(15) . . ?
C9 C5 C4 117.98(16) . . ?
C10 C5 C4 112.05(14) . . ?
C9 C5 C6 121.81(14) . . ?
C10 C5 C6 109.83(14) . . ?
C4 C5 C6 85.40(12) . . ?
C3A C4A C8A 108.97(12) . . ?
C3A C4A C5A 110.92(13) . . ?
C8A C4A C5A 87.79(12) . . ?
C1 C6 C8 109.03(12) . . ?
C1 C6 C5 112.37(12) . . ?
C8 C6 C5 87.03(12) . . ?
C9A C5A C10A 107.97(13) . . ?
C9A C5A C4A 118.33(14) . . ?
C10A C5A C4A 112.09(14) . . ?
C9A C5A C6A 121.81(13) . . ?
C10A C5A C6A 109.90(13) . . ?
C4A C5A C6A 85.23(11) . . ?
C1A C6A C8A 108.86(11) . . ?
C1A C6A C5A 112.98(12) . . ?
C8A C6A C5A 87.15(11) . . ?
C4 C8 C6 86.83(13) . . ?
C16 C11 C12 119.37(15) . . ?
C16 C11 P1 117.88(12) . . ?
C12 C11 P1 122.71(12) . . ?
C13 C12 C11 120.00(17) . . ?
C12A C11A C16A 119.46(15) . . ?
C12A C11A P1A 122.32(12) . . ?
C16A C11A P1A 118.22(13) . . ?
C14 C13 C12 120.22(18) . . ?
C13A C12A C11A 119.37(17) . . ?
C15 C14 C13 119.94(16) . . ?
C14A C13A C12A 120.80(18) . . ?
C14 C15 C16 120.38(16) . . ?
C15A C14A C13A 119.90(17) . . ?
C11 C16 C15 120.06(17) . . ?
C14A C15A C16A 120.40(18) . . ?
C15A C16A C11A 120.05(17) . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_ar240419P1
_database_code_depnum_ccdc_archive 'CCDC 2277415'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2023-08-11 deposited with the CCDC.	2023-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 O3 P'
_chemical_formula_sum            'C16 H21 O3 P'
_chemical_formula_weight         292.30

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.2826(3)
_cell_length_b                   6.9016(2)
_cell_length_c                   11.6832(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.7230(10)
_cell_angle_gamma                90
_cell_volume                     753.12(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13391
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.555
_exptl_crystal_size_mid          0.509
_exptl_crystal_size_min          0.322
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6959
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.933
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            13391
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.919
_diffrn_reflns_theta_max         25.674
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.938
_reflns_number_total             2698
_reflns_number_gt                2664
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_max     0.932
_reflns_Friedel_fraction_full    0.928

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

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX4 v2021.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²+0.2613P] 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 1180 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2698
_refine_ls_number_parameters     149
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.17423(6) 0.27499(9) 0.33579(5) 0.02574(16) Uani 1 1 d . . . . .
O1 O 0.1283(3) 0.0862(3) 0.2749(2) 0.0419(5) Uani 1 1 d . . . . .
O2 O 0.32369(18) 0.3504(3) 0.34623(17) 0.0308(4) Uani 1 1 d . . . . .
O3 O 0.08031(18) 0.4530(3) 0.26233(18) 0.0300(4) Uani 1 1 d . . . . .
C1 C 0.3214(3) 0.5440(4) 0.2930(2) 0.0261(5) Uani 1 1 d . . . . .
C2 C 0.3693(3) 0.5165(3) 0.1870(2) 0.0251(5) Uani 1 1 d . . . . .
H2 H 0.467859 0.462187 0.214131 0.030 Uiso 1 1 calc R U . . .
C3 C 0.3348(3) 0.6931(4) 0.0949(3) 0.0296(6) Uani 1 1 d . . . . .
C4 C 0.1829(3) 0.6045(4) 0.0298(2) 0.0314(5) Uani 1 1 d . . . . .
H4 H 0.135604 0.618521 -0.063974 0.038 Uiso 1 1 calc R U . . .
C5 C 0.0910(3) 0.6618(4) 0.0987(3) 0.0325(6) Uani 1 1 d . . . . .
H5A H -0.002459 0.594823 0.058850 0.039 Uiso 1 1 calc R U . . .
H5B H 0.072710 0.802960 0.088945 0.039 Uiso 1 1 calc R U . . .
C6 C 0.1602(3) 0.6122(4) 0.2396(2) 0.0260(5) Uani 1 1 d . . . . .
H6 H 0.153834 0.728035 0.288330 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4204(3) 0.6671(6) 0.4017(3) 0.0465(8) Uani 1 1 d . . . . .
H7A H 0.418834 0.800886 0.373067 0.070 Uiso 1 1 calc R U . . .
H7B H 0.518072 0.615925 0.432628 0.070 Uiso 1 1 calc R U . . .
H7C H 0.388383 0.664119 0.469759 0.070 Uiso 1 1 calc R U . . .
C8 C 0.2506(3) 0.4037(4) 0.0786(2) 0.0283(5) Uani 1 1 d . . . . .
H8A H 0.284310 0.334892 0.021713 0.034 Uiso 1 1 calc R U . . .
H8B H 0.191856 0.318211 0.106229 0.034 Uiso 1 1 calc R U . . .
C9 C 0.3502(4) 0.9016(4) 0.1421(4) 0.0468(8) Uani 1 1 d . . . . .
H9A H 0.315182 0.990286 0.070027 0.070 Uiso 1 1 calc R U . . .
H9B H 0.451209 0.929055 0.195122 0.070 Uiso 1 1 calc R U . . .
H9C H 0.294058 0.919263 0.191546 0.070 Uiso 1 1 calc R U . . .
C10 C 0.4176(3) 0.6747(4) 0.0123(3) 0.0381(6) Uani 1 1 d . . . . .
H10A H 0.380672 0.769192 -0.056498 0.057 Uiso 1 1 calc R U . . .
H10B H 0.405594 0.543559 -0.022826 0.057 Uiso 1 1 calc R U . . .
H10C H 0.519506 0.699580 0.063547 0.057 Uiso 1 1 calc R U . . .
C11 C 0.1789(6) 0.2864(9) 0.4905(4) 0.0387(5) Uani 0.531(8) 1 d G . P A 1
C12 C 0.1830(6) 0.1186(8) 0.5578(5) 0.0387(5) Uani 0.531(8) 1 d G . P A 1
H12 H 0.188608 -0.004408 0.523587 0.046 Uiso 0.531(8) 1 calc R U P A 1
C13 C 0.1790(5) 0.1308(9) 0.6750(4) 0.0387(5) Uani 0.531(8) 1 d G . P A 1
H13 H 0.181786 0.016073 0.720923 0.046 Uiso 0.531(8) 1 calc R U P A 1
C14 C 0.1708(5) 0.3107(11) 0.7250(3) 0.0387(5) Uani 0.531(8) 1 d G . P A 1
H14 H 0.168050 0.319048 0.805096 0.046 Uiso 0.531(8) 1 calc R U P A 1
C15 C 0.1667(5) 0.4785(9) 0.6578(4) 0.0387(5) Uani 0.531(8) 1 d G . P A 1
H15 H 0.161138 0.601543 0.691935 0.046 Uiso 0.531(8) 1 calc R U P A 1
C16 C 0.1708(6) 0.4664(8) 0.5405(4) 0.0387(5) Uani 0.531(8) 1 d G . P A 1
H16 H 0.167960 0.581065 0.494599 0.046 Uiso 0.531(8) 1 calc R U P A 1
C11A C 0.1753(8) 0.2642(10) 0.4904(5) 0.0387(5) Uani 0.469(8) 1 d G . P A 2
C12A C 0.1979(7) 0.0825(9) 0.5467(5) 0.0387(5) Uani 0.469(8) 1 d G . P A 2
H12A H 0.212042 -0.026934 0.503906 0.046 Uiso 0.469(8) 1 calc R U P A 2
C13A C 0.1998(6) 0.0609(10) 0.6657(5) 0.0387(5) Uani 0.469(8) 1 d G . P A 2
H13A H 0.215310 -0.063277 0.704225 0.046 Uiso 0.469(8) 1 calc R U P A 2
C14A C 0.1792(5) 0.2210(13) 0.7283(4) 0.0387(5) Uani 0.469(8) 1 d G . P A 2
H14A H 0.180491 0.206265 0.809675 0.046 Uiso 0.469(8) 1 calc R U P A 2
C15A C 0.1565(6) 0.4027(11) 0.6720(5) 0.0387(5) Uani 0.469(8) 1 d G . P A 2
H15A H 0.142403 0.512152 0.714806 0.046 Uiso 0.469(8) 1 calc R U P A 2
C16A C 0.1546(7) 0.4243(9) 0.5530(5) 0.0387(5) Uani 0.469(8) 1 d G . P A 2
H16A H 0.139133 0.548499 0.514487 0.046 Uiso 0.469(8) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.465(2) . ?
P1 O3 1.5767(19) . ?
P1 O2 1.5781(19) . ?
P1 C11 1.790(3) . ?
P1 C11A 1.803(4) . ?
O2 C1 1.470(3) . ?
O3 C6 1.461(3) . ?
C1 C7 1.513(3) . ?
C1 C2 1.524(3) . ?
C1 C6 1.579(3) . ?
C2 C8 1.551(3) . ?
C2 C3 1.565(3) . ?
C3 C9 1.525(4) . ?
C3 C10 1.536(4) . ?
C3 C4 1.549(4) . ?
C4 C5 1.527(4) . ?
C4 C8 1.548(3) . ?
C5 C6 1.534(4) . ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C11A C12A 1.3900 . ?
C11A C16A 1.3900 . ?
C12A C13A 1.3900 . ?
C13A C14A 1.3900 . ?
C14A C15A 1.3900 . ?
C15A C16A 1.3900 . ?

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 O3 115.42(12) . . ?
O1 P1 O2 115.87(11) . . ?
O3 P1 O2 98.06(10) . . ?
O1 P1 C11 113.4(2) . . ?
O3 P1 C11 105.5(2) . . ?
O2 P1 C11 107.1(2) . . ?
O1 P1 C11A 108.4(2) . . ?
O3 P1 C11A 108.9(2) . . ?
O2 P1 C11A 109.8(2) . . ?
C1 O2 P1 115.10(15) . . ?
C6 O3 P1 114.95(15) . . ?
O2 C1 C7 105.6(2) . . ?
O2 C1 C2 106.10(19) . . ?
C7 C1 C2 114.8(2) . . ?
O2 C1 C6 105.44(19) . . ?
C7 C1 C6 113.0(2) . . ?
C2 C1 C6 111.00(19) . . ?
C1 C2 C8 108.3(2) . . ?
C1 C2 C3 113.9(2) . . ?
C8 C2 C3 87.44(19) . . ?
C9 C3 C10 107.7(2) . . ?
C9 C3 C4 118.7(2) . . ?
C10 C3 C4 111.6(2) . . ?
C9 C3 C2 121.8(2) . . ?
C10 C3 C2 110.0(2) . . ?
C4 C3 C2 85.51(18) . . ?
C5 C4 C8 108.6(2) . . ?
C5 C4 C3 111.0(2) . . ?
C8 C4 C3 88.10(19) . . ?
C4 C5 C6 113.3(2) . . ?
O3 C6 C5 108.6(2) . . ?
O3 C6 C1 106.35(19) . . ?
C5 C6 C1 115.5(2) . . ?
C4 C8 C2 86.02(18) . . ?
C12 C11 C16 120.0 . . ?
C12 C11 P1 121.0(3) . . ?
C16 C11 P1 118.9(3) . . ?
C11 C12 C13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C15 C14 C13 120.0 . . ?
C16 C15 C14 120.0 . . ?
C15 C16 C11 120.0 . . ?
C12A C11A C16A 120.0 . . ?
C12A C11A P1 116.2(3) . . ?
C16A C11A P1 123.8(3) . . ?
C13A C12A C11A 120.0 . . ?
C12A C13A C14A 120.0 . . ?
C13A C14A C15A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C15A C16A C11A 120.0 . . ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_ar230606P1a
_database_code_depnum_ccdc_archive 'CCDC 2277414'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2023-08-11 deposited with the CCDC.	2023-12-12 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         'C16 H21 O3 P'
_chemical_formula_sum            'C16 H21 O3 P'
_chemical_formula_weight         292.30

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'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.2898(10)
_cell_length_b                   6.9020(6)
_cell_length_c                   11.6872(9)
_cell_angle_alpha                90
_cell_angle_beta                 114.772(3)
_cell_angle_gamma                90
_cell_volume                     753.65(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    29459
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.133
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6431
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.862
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            29459
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.521
_diffrn_reflns_theta_max         25.849
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2874
_reflns_number_gt                2709
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.995

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

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX4 v2021.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0709P)²+0.0529P] 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 1197 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2874
_refine_ls_number_parameters     179
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.17418(6) 0.72181(11) 0.33576(5) 0.0303(2) Uani 1 1 d . . . . .
O1 O 0.1285(3) 0.9104(3) 0.2752(2) 0.0469(6) Uani 1 1 d . . . . .
O2 O 0.0807(2) 0.5436(3) 0.26229(19) 0.0346(5) Uani 1 1 d . . . . .
O3 O 0.3240(2) 0.6466(3) 0.34608(17) 0.0361(5) Uani 1 1 d . . . . .
C1 C 0.3209(3) 0.4530(4) 0.2929(2) 0.0309(6) Uani 1 1 d . . . . .
C2 C 0.1606(3) 0.3844(4) 0.2398(2) 0.0305(5) Uani 1 1 d . . . . .
H2A H 0.154465 0.268784 0.288789 0.037 Uiso 1 1 calc R U . . .
C3 C 0.0908(3) 0.3342(4) 0.0986(3) 0.0375(6) Uani 1 1 d . . . . .
H3A H 0.072778 0.192976 0.088932 0.045 Uiso 1 1 calc R U . . .
H3B H -0.002841 0.400873 0.058734 0.045 Uiso 1 1 calc R U . . .
C4 C 0.1828(3) 0.3923(4) 0.0300(2) 0.0352(6) Uani 1 1 d . . . . .
H4A H 0.135454 0.378502 -0.063814 0.042 Uiso 1 1 calc R U . . .
C5 C 0.2503(3) 0.5928(4) 0.0786(2) 0.0330(6) Uani 1 1 d . . . . .
H5A H 0.191724 0.678129 0.106411 0.040 Uiso 1 1 calc R U . . .
H5B H 0.283652 0.661705 0.021565 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3694(3) 0.4803(4) 0.1869(2) 0.0302(5) Uani 1 1 d . . . . .
H6A H 0.467925 0.534746 0.214088 0.036 Uiso 1 1 calc R U . . .
C7 C 0.4200(3) 0.3296(6) 0.4016(3) 0.0513(9) Uani 1 1 d . . . . .
H7A H 0.517289 0.382226 0.433647 0.077 Uiso 1 1 calc R U . . .
H7B H 0.419850 0.196406 0.372403 0.077 Uiso 1 1 calc R U . . .
H7C H 0.386975 0.330224 0.468967 0.077 Uiso 1 1 calc R U . . .
C8 C 0.3345(3) 0.3039(4) 0.0946(3) 0.0354(6) Uani 1 1 d . . . . .
C9 C 0.3506(5) 0.0956(5) 0.1424(4) 0.0525(9) Uani 1 1 d . . . . .
H9A H 0.314122 0.006507 0.070533 0.079 Uiso 1 1 calc R U . . .
H9B H 0.296133 0.078561 0.193251 0.079 Uiso 1 1 calc R U . . .
H9C H 0.451923 0.067965 0.194152 0.079 Uiso 1 1 calc R U . . .
C10 C 0.4180(4) 0.3215(5) 0.0124(3) 0.0430(7) Uani 1 1 d . . . . .
H10A H 0.383225 0.223987 -0.054695 0.065 Uiso 1 1 calc R U . . .
H10B H 0.520108 0.300643 0.064550 0.065 Uiso 1 1 calc R U . . .
H10C H 0.403663 0.451156 -0.025136 0.065 Uiso 1 1 calc R U . . .
C11 C 0.180(3) 0.708(3) 0.4913(14) 0.0362(19) Uani 0.59(2) 1 d G . P A 1
C12 C 0.169(2) 0.531(2) 0.5433(15) 0.050(2) Uani 0.59(2) 1 d G . P A 1
H12A H 0.164659 0.414562 0.499040 0.059 Uiso 0.59(2) 1 calc R U P A 1
C13 C 0.1631(19) 0.525(2) 0.6601(14) 0.063(3) Uani 0.59(2) 1 d G . P A 1
H13A H 0.155565 0.404472 0.695683 0.076 Uiso 0.59(2) 1 calc R U P A 1
C14 C 0.1688(15) 0.696(3) 0.7249(11) 0.060(4) Uani 0.59(2) 1 d G . P A 1
H14A H 0.165137 0.692262 0.804776 0.072 Uiso 0.59(2) 1 calc R U P A 1
C15 C 0.1799(18) 0.873(2) 0.6729(15) 0.060(3) Uani 0.59(2) 1 d G . P A 1
H15A H 0.183803 0.990143 0.717227 0.072 Uiso 0.59(2) 1 calc R U P A 1
C16 C 0.185(2) 0.879(2) 0.5561(16) 0.0454(18) Uani 0.59(2) 1 d G . P A 1
H16A H 0.192897 1.000237 0.520585 0.055 Uiso 0.59(2) 1 calc R U P A 1
C11' C 0.173(4) 0.739(4) 0.489(2) 0.0362(19) Uani 0.41(2) 1 d G . P A 2
C12' C 0.156(4) 0.576(3) 0.551(2) 0.050(2) Uani 0.41(2) 1 d G . P A 2
H12B H 0.141264 0.453021 0.511584 0.059 Uiso 0.41(2) 1 calc R U P A 2
C13' C 0.162(3) 0.594(3) 0.671(2) 0.063(3) Uani 0.41(2) 1 d G . P A 2
H13B H 0.150270 0.482728 0.714224 0.076 Uiso 0.41(2) 1 calc R U P A 2
C14' C 0.184(2) 0.775(3) 0.7293(16) 0.060(4) Uani 0.41(2) 1 d G . P A 2
H14B H 0.187319 0.786604 0.811589 0.072 Uiso 0.41(2) 1 calc R U P A 2
C15' C 0.200(3) 0.937(3) 0.667(2) 0.060(3) Uani 0.41(2) 1 d G . P A 2
H15B H 0.215364 1.060776 0.706315 0.072 Uiso 0.41(2) 1 calc R U P A 2
C16' C 0.195(3) 0.920(3) 0.546(2) 0.0454(18) Uani 0.41(2) 1 d G . P A 2
H16B H 0.206359 1.031074 0.503674 0.055 Uiso 0.41(2) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.462(2) . ?
P1 O2 1.576(2) . ?
P1 O3 1.582(2) . ?
P1 C11' 1.795(16) . ?
P1 C11 1.798(11) . ?
O2 C2 1.461(3) . ?
O3 C1 1.469(3) . ?
C1 C7 1.515(4) . ?
C1 C6 1.529(3) . ?
C1 C2 1.572(3) . ?
C2 C3 1.538(4) . ?
C3 C4 1.529(4) . ?
C4 C5 1.546(4) . ?
C4 C8 1.547(4) . ?
C5 C6 1.551(4) . ?
C6 C8 1.565(4) . ?
C8 C9 1.526(4) . ?
C8 C10 1.538(4) . ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C11' C12' 1.3900 . ?
C11' C16' 1.3900 . ?
C12' C13' 1.3900 . ?
C13' C14' 1.3900 . ?
C14' C15' 1.3900 . ?
C15' C16' 1.3900 . ?

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 O2 115.58(12) . . ?
O1 P1 O3 115.72(12) . . ?
O2 P1 O3 97.96(11) . . ?
O1 P1 C11' 106.7(9) . . ?
O2 P1 C11' 109.7(9) . . ?
O3 P1 C11' 111.0(11) . . ?
O1 P1 C11 113.8(6) . . ?
O2 P1 C11 105.3(6) . . ?
O3 P1 C11 106.8(8) . . ?
C2 O2 P1 115.07(16) . . ?
C1 O3 P1 114.74(16) . . ?
O3 C1 C7 105.6(2) . . ?
O3 C1 C6 105.9(2) . . ?
C7 C1 C6 114.5(2) . . ?
O3 C1 C2 105.9(2) . . ?
C7 C1 C2 112.9(2) . . ?
C6 C1 C2 111.2(2) . . ?
O2 C2 C3 108.5(2) . . ?
O2 C2 C1 106.2(2) . . ?
C3 C2 C1 115.6(2) . . ?
C4 C3 C2 113.0(2) . . ?
C3 C4 C5 108.9(2) . . ?
C3 C4 C8 111.1(2) . . ?
C5 C4 C8 88.1(2) . . ?
C4 C5 C6 86.09(19) . . ?
C1 C6 C5 107.9(2) . . ?
C1 C6 C8 113.8(2) . . ?
C5 C6 C8 87.3(2) . . ?
C9 C8 C10 107.5(3) . . ?
C9 C8 C4 118.9(3) . . ?
C10 C8 C4 112.1(3) . . ?
C9 C8 C6 121.5(3) . . ?
C10 C8 C6 110.0(2) . . ?
C4 C8 C6 85.5(2) . . ?
C12 C11 C16 120.0 . . ?
C12 C11 P1 120.9(9) . . ?
C16 C11 P1 118.9(9) . . ?
C13 C12 C11 120.0 . . ?
C14 C13 C12 120.0 . . ?
C15 C14 C13 120.0 . . ?
C14 C15 C16 120.0 . . ?
C15 C16 C11 120.0 . . ?
C12' C11' C16' 120.0 . . ?
C12' C11' P1 121.5(14) . . ?
C16' C11' P1 118.4(13) . . ?
C13' C12' C11' 120.0 . . ?
C14' C13' C12' 120.0 . . ?
C13' C14' C15' 120.0 . . ?
C16' C15' C14' 120.0 . . ?
C15' C16' C11' 120.0 . . ?

_refine_diff_density_max         0.374
_refine_diff_density_min         -0.265
_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_ar230606P1
_database_code_depnum_ccdc_archive 'CCDC 2277413'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2023-08-11 deposited with the CCDC.	2023-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 O3 P'
_chemical_formula_sum            'C16 H21 O3 P'
_chemical_formula_weight         292.30

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'
P P 0.1023 0.0942 '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'

_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                   9.9615(6)
_cell_length_b                   11.5646(7)
_cell_length_c                   26.2104(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3019.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    45757
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.156
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6032
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.808
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            45757
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.568
_diffrn_reflns_theta_max         28.414
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7542
_reflns_number_gt                7145
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.998

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

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX4 v2021.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²+0.3581P] 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 2958 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         7542
_refine_ls_number_parameters     367
_refine_ls_number_restraints     350
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.071
_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 0.87985(5) 0.49798(5) 0.43413(2) 0.02691(12) Uani 1 1 d . . . . .
P2 P 0.70982(6) 0.79119(5) 0.15914(2) 0.03013(13) Uani 1 1 d . . . . .
O3 O 0.78063(15) 0.43307(12) 0.39600(6) 0.0268(3) Uani 1 1 d . . . . .
O2 O 0.94604(16) 0.38677(14) 0.45913(6) 0.0328(3) Uani 1 1 d . . . . .
O1 O 0.97197(18) 0.58133(15) 0.41050(7) 0.0395(4) Uani 1 1 d . . . . .
O4 O 0.78030(15) 0.91401(12) 0.15345(6) 0.0283(3) Uani 1 1 d . . . . .
O5 O 0.56870(16) 0.83861(14) 0.17859(7) 0.0355(4) Uani 1 1 d . . . . .
O6 O 0.7084(2) 0.71775(16) 0.11346(7) 0.0486(5) Uani 1 1 d . . . . .
C1 C 0.82146(19) 0.31194(16) 0.38647(8) 0.0236(4) Uani 1 1 d . . . . .
C10 C 0.5945(3) 0.0379(2) 0.38265(12) 0.0448(6) Uani 1 1 d . . . . .
H10A H 0.590196 0.029458 0.345487 0.067 Uiso 1 1 calc R U . . .
H10B H 0.513854 0.077892 0.394777 0.067 Uiso 1 1 calc R U . . .
H10C H 0.599909 -0.038656 0.398507 0.067 Uiso 1 1 calc R U . . .
C11 C 0.7789(2) 0.56477(18) 0.48192(8) 0.0294(4) Uani 1 1 d . . . . .
C12 C 0.7388(3) 0.6795(2) 0.47442(10) 0.0391(5) Uani 1 1 d . . . . .
H12 H 0.768487 0.720852 0.445189 0.047 Uiso 1 1 calc R U . . .
C13 C 0.6557(3) 0.7328(2) 0.50979(12) 0.0491(7) Uani 1 1 d . . . . .
H13 H 0.627315 0.810188 0.504285 0.059 Uiso 1 1 calc R U . . .
C14 C 0.6141(3) 0.6747(3) 0.55273(11) 0.0499(7) Uani 1 1 d . . . . .
H14 H 0.556931 0.711833 0.576696 0.060 Uiso 1 1 calc R U . . .
C15 C 0.6555(3) 0.5624(3) 0.56088(10) 0.0450(6) Uani 1 1 d . . . . .
H15 H 0.627585 0.522938 0.590842 0.054 Uiso 1 1 calc R U . . .
C16 C 0.7378(2) 0.5060(2) 0.52578(9) 0.0360(5) Uani 1 1 d . . . . .
H16 H 0.765608 0.428590 0.531632 0.043 Uiso 1 1 calc R U . . .
C101 C 0.67990(19) 1.00243(19) 0.13888(8) 0.0266(4) Uani 1 1 d . . . . .
C102 C 0.5440(2) 0.95739(19) 0.16189(10) 0.0331(5) Uani 1 1 d . . . . .
H102 H 0.475001 0.956040 0.134173 0.040 Uiso 1 1 calc R U . . .
C103 C 0.4879(3) 1.0272(2) 0.20711(12) 0.0488(7) Uani 1 1 d . . . . .
H10D H 0.394466 1.050369 0.199338 0.059 Uiso 1 1 calc R U . . .
H10E H 0.485747 0.977010 0.237713 0.059 Uiso 1 1 calc R U . . .
C104 C 0.5699(3) 1.1349(2) 0.21903(10) 0.0415(6) Uani 1 1 d . . . . .
H104 H 0.535729 1.182950 0.247968 0.050 Uiso 1 1 calc R U . . .
C105 C 0.6033(2) 1.20282(19) 0.16923(9) 0.0332(5) Uani 1 1 d . . . . .
C106 C 0.7234(2) 1.11534(18) 0.16353(8) 0.0279(4) Uani 1 1 d . . . . .
H106 H 0.808288 1.149291 0.149703 0.034 Uiso 1 1 calc R U . . .
C107 C 0.7192(3) 1.1014(2) 0.22224(9) 0.0386(5) Uani 1 1 d . . . . .
H10F H 0.735269 1.021421 0.234264 0.046 Uiso 1 1 calc R U . . .
H10G H 0.775509 1.157637 0.240993 0.046 Uiso 1 1 calc R U . . .
C108 C 0.6807(3) 1.0075(2) 0.08086(8) 0.0390(5) Uani 1 1 d . . . . .
H10H H 0.619850 1.068783 0.069318 0.058 Uiso 1 1 calc R U . . .
H10I H 0.650788 0.933088 0.067058 0.058 Uiso 1 1 calc R U . . .
H10J H 0.771841 1.023975 0.068842 0.058 Uiso 1 1 calc R U . . .
C109 C 0.4940(3) 1.2144(2) 0.12894(11) 0.0464(6) Uani 1 1 d . . . . .
H10K H 0.531227 1.251271 0.098413 0.070 Uiso 1 1 calc R U . . .
H10L H 0.420515 1.261742 0.142415 0.070 Uiso 1 1 calc R U . . .
H10M H 0.459792 1.137469 0.120085 0.070 Uiso 1 1 calc R U . . .
C110 C 0.6584(3) 1.3242(2) 0.18068(12) 0.0480(7) Uani 1 1 d . . . . .
H11A H 0.696499 1.357444 0.149490 0.072 Uiso 1 1 calc R U . . .
H11B H 0.728283 1.318940 0.206878 0.072 Uiso 1 1 calc R U . . .
H11C H 0.585357 1.373727 0.192988 0.072 Uiso 1 1 calc R U . . .
C111 C 0.7869(2) 0.72040(18) 0.21194(8) 0.0293(4) Uani 1 1 d . . . . .
C112 C 0.8037(3) 0.7730(2) 0.25941(10) 0.0412(6) Uani 1 1 d . . . . .
H112 H 0.768668 0.848226 0.265203 0.049 Uiso 1 1 calc R U . . .
C113 C 0.8715(3) 0.7158(2) 0.29822(11) 0.0464(6) Uani 1 1 d . . . . .
H113 H 0.882398 0.751885 0.330521 0.056 Uiso 1 1 calc R U . . .
C114 C 0.9232(3) 0.6059(2) 0.28985(11) 0.0420(6) Uani 1 1 d . . . . .
H114 H 0.971217 0.567479 0.316192 0.050 Uiso 1 1 calc R U . . .
C115 C 0.9051(3) 0.5528(2) 0.24349(10) 0.0410(6) Uani 1 1 d . . . . .
H115 H 0.939808 0.477287 0.238043 0.049 Uiso 1 1 calc R U . . .
C116 C 0.8362(3) 0.6087(2) 0.20444(10) 0.0360(5) Uani 1 1 d . . . . .
H116 H 0.822819 0.570872 0.172677 0.043 Uiso 1 1 calc R U . . .
C2 C 0.9153(2) 0.27939(18) 0.43231(8) 0.0272(4) Uani 1 1 d . . . . .
H2 H 1.000839 0.247078 0.418297 0.033 Uiso 1 1 calc R U . . .
C3 C 0.8561(2) 0.1912(2) 0.47037(9) 0.0333(5) Uani 1 1 d . . . . .
H3A H 0.919382 0.125749 0.473974 0.040 Uiso 1 1 calc R U . . .
H3B H 0.847460 0.228643 0.504190 0.040 Uiso 1 1 calc R U . . .
C4 C 0.7192(3) 0.1443(2) 0.45441(9) 0.0341(5) Uani 1 1 d . . . . .
H4 H 0.678273 0.086884 0.478315 0.041 Uiso 1 1 calc R U . . .
C5 C 0.7193(2) 0.10867(18) 0.39704(9) 0.0302(4) Uani 1 1 d . . . . .
C6 C 0.6935(2) 0.24050(17) 0.38618(8) 0.0258(4) Uani 1 1 d . . . . .
H6 H 0.631550 0.256652 0.357026 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6278(2) 0.2472(2) 0.43951(9) 0.0332(5) Uani 1 1 d . . . . .
H7A H 0.530690 0.229094 0.439795 0.040 Uiso 1 1 calc R U . . .
H7B H 0.647085 0.319582 0.458299 0.040 Uiso 1 1 calc R U . . .
C8 C 0.8929(2) 0.31204(18) 0.33530(8) 0.0309(4) Uani 1 1 d . . . . .
H8A H 0.916301 0.232554 0.325886 0.046 Uiso 1 1 calc R U . . .
H8B H 0.974841 0.358592 0.337737 0.046 Uiso 1 1 calc R U . . .
H8C H 0.833609 0.345051 0.309256 0.046 Uiso 1 1 calc R U . . .
C9 C 0.8416(3) 0.0457(2) 0.37594(10) 0.0374(5) Uani 1 1 d . . . . .
H9A H 0.923023 0.088910 0.384654 0.056 Uiso 1 1 calc R U . . .
H9B H 0.833905 0.039505 0.338767 0.056 Uiso 1 1 calc R U . . .
H9C H 0.846478 -0.031944 0.390838 0.056 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 1.4679(18) . ?
P1 O2 1.5869(17) . ?
P1 O3 1.5935(15) . ?
P1 C11 1.782(2) . ?
P2 O6 1.4680(18) . ?
P2 O4 1.5914(15) . ?
P2 O5 1.5927(18) . ?
P2 C111 1.782(2) . ?
O3 C1 1.480(2) . ?
O2 C2 1.459(2) . ?
O4 C101 1.480(2) . ?
O5 C102 1.463(3) . ?
C1 C8 1.518(3) . ?
C1 C6 1.519(3) . ?
C1 C2 1.568(3) . ?
C10 C5 1.535(3) . ?
C11 C16 1.397(3) . ?
C11 C12 1.400(3) . ?
C12 C13 1.387(4) . ?
C13 C14 1.374(5) . ?
C14 C15 1.380(4) . ?
C15 C16 1.394(3) . ?
C101 C106 1.520(3) . ?
C101 C108 1.522(3) . ?
C101 C102 1.571(3) . ?
C102 C103 1.539(4) . ?
C103 C104 1.522(4) . ?
C104 C107 1.539(4) . ?
C104 C105 1.559(3) . ?
C105 C109 1.523(4) . ?
C105 C110 1.537(3) . ?
C105 C106 1.574(3) . ?
C106 C107 1.548(3) . ?
C111 C112 1.395(3) . ?
C111 C116 1.396(3) . ?
C112 C113 1.388(4) . ?
C113 C114 1.389(4) . ?
C114 C115 1.373(4) . ?
C115 C116 1.391(3) . ?
C2 C3 1.544(3) . ?
C3 C4 1.526(3) . ?
C4 C7 1.548(3) . ?
C4 C5 1.559(3) . ?
C5 C9 1.523(3) . ?
C5 C6 1.572(3) . ?
C6 C7 1.545(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 116.54(10) . . ?
O1 P1 O3 115.63(10) . . ?
O2 P1 O3 97.76(8) . . ?
O1 P1 C11 111.38(10) . . ?
O2 P1 C11 107.17(10) . . ?
O3 P1 C11 107.15(9) . . ?
O6 P2 O4 116.35(11) . . ?
O6 P2 O5 116.87(12) . . ?
O4 P2 O5 96.44(8) . . ?
O6 P2 C111 111.82(11) . . ?
O4 P2 C111 107.03(9) . . ?
O5 P2 C111 106.85(10) . . ?
C1 O3 P1 112.41(12) . . ?
C2 O2 P1 113.80(13) . . ?
C101 O4 P2 110.04(13) . . ?
C102 O5 P2 112.10(14) . . ?
C8 C1 C6 112.90(17) . . ?
C8 C1 C2 113.42(17) . . ?
C6 C1 C2 111.94(17) . . ?
C16 C11 C12 119.5(2) . . ?
C16 C11 P1 122.22(17) . . ?
C12 C11 P1 118.23(18) . . ?
C13 C12 C11 119.8(2) . . ?
C14 C13 C12 120.7(3) . . ?
C13 C14 C15 119.7(3) . . ?
C14 C15 C16 120.9(3) . . ?
C15 C16 C11 119.2(2) . . ?
O4 C101 C106 106.92(16) . . ?
O4 C101 C108 106.32(17) . . ?
C106 C101 C108 112.96(19) . . ?
O4 C101 C102 104.73(16) . . ?
C106 C101 C102 111.56(18) . . ?
C108 C101 C102 113.62(19) . . ?
O5 C102 C103 108.8(2) . . ?
O5 C102 C101 106.33(17) . . ?
C103 C102 C101 115.76(19) . . ?
C104 C103 C102 113.1(2) . . ?
C103 C104 C107 108.9(2) . . ?
C103 C104 C105 110.8(2) . . ?
C107 C104 C105 88.08(19) . . ?
C109 C105 C110 108.1(2) . . ?
C109 C105 C104 118.1(2) . . ?
C110 C105 C104 111.9(2) . . ?
C109 C105 C106 122.3(2) . . ?
C110 C105 C106 109.6(2) . . ?
C104 C105 C106 85.29(17) . . ?
C101 C106 C107 108.97(18) . . ?
C101 C106 C105 112.06(18) . . ?
C107 C106 C105 87.23(17) . . ?
C104 C107 C106 86.91(18) . . ?
C112 C111 C116 119.1(2) . . ?
C112 C111 P2 122.98(17) . . ?
C116 C111 P2 117.88(18) . . ?
C113 C112 C111 120.3(2) . . ?
C112 C113 C114 120.0(3) . . ?
C115 C114 C113 120.0(2) . . ?
C114 C115 C116 120.5(2) . . ?
C115 C116 C111 120.0(2) . . ?
O2 C2 C3 109.31(18) . . ?
O2 C2 C1 106.84(15) . . ?
C3 C2 C1 115.19(17) . . ?
C4 C3 C2 113.53(18) . . ?
C3 C4 C7 108.75(18) . . ?
C3 C4 C5 110.96(19) . . ?
C7 C4 C5 87.72(17) . . ?
C9 C5 C10 107.67(18) . . ?
C9 C5 C4 118.5(2) . . ?
C10 C5 C4 112.2(2) . . ?
C9 C5 C6 121.93(19) . . ?
C10 C5 C6 109.88(19) . . ?
C4 C5 C6 85.30(16) . . ?
C1 C6 C7 108.88(17) . . ?
C1 C6 C5 112.93(17) . . ?
C7 C6 C5 87.37(16) . . ?
C6 C7 C4 86.60(16) . . ?

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.047

