# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_g511
_database_code_depnum_ccdc_archive 'CCDC 2005765'
loop_
_audit_author_name
_audit_author_address
'Qijian Ni'
;Anhui Normal University
China
;
_audit_update_record             
;
2020-05-26 deposited with the CCDC.	2020-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 O3 P'
_chemical_formula_sum            'C24 H19 O3 P'
_chemical_formula_weight         386.36

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                   14.464(6)
_cell_length_b                   13.000(5)
_cell_length_c                   10.236(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.227(10)
_cell_angle_gamma                90
_cell_volume                     1909.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1259
_cell_measurement_theta_min      2.545
_cell_measurement_theta_max      29.362

_exptl_crystal_description       'prism frag'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.567
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.174
_exptl_absorpt_coefficient_mu    0.167
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   Sadabs
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31186
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.545
_diffrn_reflns_theta_max         29.362
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5211
_reflns_number_gt                3840
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 v2016.6.0'
_computing_cell_refinement       
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2016.6.0'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0742P)²+0.7139P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5211
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1326
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.72730(3) 0.00953(3) 0.48653(4) 0.01356(13) Uani 1 1 d . . . . .
O1 O 0.63797(9) 0.01727(10) 0.40156(13) 0.0172(3) Uani 1 1 d . . . . .
O2 O 0.78600(9) 0.11451(9) 0.50190(12) 0.0159(3) Uani 1 1 d . . . . .
O3 O 0.71891(9) -0.02704(10) 0.63187(13) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.68497(13) 0.20248(14) 0.63363(17) 0.0147(4) Uani 1 1 d . . . . .
C1 C 0.75129(13) 0.20607(13) 0.55264(17) 0.0141(4) Uani 1 1 d . . . . .
C19 C 0.80938(13) -0.07877(14) 0.43397(19) 0.0176(4) Uani 1 1 d . . . . .
C14 C 0.48883(13) 0.27460(15) 0.90960(18) 0.0167(4) Uani 1 1 d . . . . .
H14 H 0.5194 0.3377 0.8965 0.020 Uiso 1 1 calc R U . . .
C5 C 0.63381(13) 0.12218(14) 0.69420(17) 0.0163(4) Uani 1 1 d . . . . .
C4 C 0.58322(13) 0.19173(14) 0.75512(17) 0.0151(4) Uani 1 1 d . . . . .
C13 C 0.51187(12) 0.18602(14) 0.84239(17) 0.0146(4) Uani 1 1 d . . . . .
C15 C 0.42184(13) 0.27072(15) 0.99492(18) 0.0188(4) Uani 1 1 d . . . . .
H15 H 0.4069 0.3309 1.0406 0.023 Uiso 1 1 calc R U . . .
C16 C 0.37627(14) 0.17840(16) 1.01373(19) 0.0209(4) Uani 1 1 d . . . . .
H16 H 0.3299 0.1759 1.0717 0.025 Uiso 1 1 calc R U . . .
C7 C 0.79733(13) 0.29835(14) 0.50798(18) 0.0157(4) Uani 1 1 d . . . . .
C18 C 0.46581(13) 0.09315(15) 0.86296(18) 0.0183(4) Uani 1 1 d . . . . .
H18 H 0.4809 0.0325 0.8185 0.022 Uiso 1 1 calc R U . . .
C3 C 0.63064(13) 0.28433(14) 0.70067(18) 0.0167(4) Uani 1 1 d . . . . .
H3A H 0.6690 0.3261 0.7679 0.020 Uiso 1 1 calc R U . . .
H3B H 0.5891 0.3278 0.6394 0.020 Uiso 1 1 calc R U . . .
C17 C 0.39841(14) 0.08991(15) 0.94798(19) 0.0210(4) Uani 1 1 d . . . . .
H17 H 0.3673 0.0271 0.9613 0.025 Uiso 1 1 calc R U . . .
C8 C 0.84107(13) 0.29546(15) 0.39367(19) 0.0185(4) Uani 1 1 d . . . . .
H8 H 0.8415 0.2333 0.3450 0.022 Uiso 1 1 calc R U . . .
C12 C 0.79930(14) 0.39102(15) 0.5783(2) 0.0231(4) Uani 1 1 d . . . . .
H12 H 0.7707 0.3948 0.6568 0.028 Uiso 1 1 calc R U . . .
C6 C 0.63785(16) 0.00800(15) 0.6904(2) 0.0225(4) Uani 1 1 d . . . . .
H6A H 0.6407 -0.0195 0.7810 0.027 Uiso 1 1 calc R U . . .
H6B H 0.5806 -0.0188 0.6384 0.027 Uiso 1 1 calc R U . . .
C10 C 0.88487(15) 0.47383(16) 0.4202(2) 0.0271(5) Uani 1 1 d . . . . .
H10 H 0.9140 0.5332 0.3900 0.032 Uiso 1 1 calc R U . . .
C20 C 0.77929(15) -0.14541(15) 0.3305(2) 0.0237(4) Uani 1 1 d . . . . .
H20 H 0.7174 -0.1408 0.2871 0.028 Uiso 1 1 calc R U . . .
C11 C 0.84280(16) 0.47762(16) 0.5343(2) 0.0286(5) Uani 1 1 d . . . . .
H11 H 0.8436 0.5399 0.5830 0.034 Uiso 1 1 calc R U . . .
C9 C 0.88397(14) 0.38267(16) 0.3506(2) 0.0229(4) Uani 1 1 d . . . . .
H9 H 0.9130 0.3795 0.2725 0.028 Uiso 1 1 calc R U . . .
C24 C 0.90018(15) -0.08554(17) 0.4972(2) 0.0299(5) Uani 1 1 d . . . . .
H24 H 0.9208 -0.0406 0.5681 0.036 Uiso 1 1 calc R U . . .
C21 C 0.84045(18) -0.21887(17) 0.2908(3) 0.0343(6) Uani 1 1 d . . . . .
H21 H 0.8203 -0.2645 0.2204 0.041 Uiso 1 1 calc R U . . .
C22 C 0.93025(17) -0.22478(17) 0.3542(3) 0.0393(6) Uani 1 1 d . . . . .
H22 H 0.9718 -0.2751 0.3277 0.047 Uiso 1 1 calc R U . . .
C23 C 0.96030(17) -0.15836(19) 0.4558(3) 0.0421(7) Uani 1 1 d . . . . .
H23 H 1.0226 -0.1625 0.4978 0.050 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 1.4674(15) . ?
P1 O3 1.5810(15) . ?
P1 O2 1.6046(14) . ?
P1 C19 1.7826(19) . ?
O2 C1 1.416(2) . ?
O3 C6 1.455(2) . ?
C2 C1 1.345(3) . ?
C2 C5 1.462(3) . ?
C2 C3 1.535(3) . ?
C1 C7 1.472(2) . ?
C19 C24 1.392(3) . ?
C19 C20 1.395(3) . ?
C14 C15 1.385(3) . ?
C14 C13 1.403(3) . ?
C14 H14 0.9500 . ?
C5 C4 1.363(3) . ?
C5 C6 1.486(3) . ?
C4 C13 1.449(3) . ?
C4 C3 1.525(3) . ?
C13 C18 1.408(3) . ?
C15 C16 1.394(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9500 . ?
C7 C8 1.399(3) . ?
C7 C12 1.402(3) . ?
C18 C17 1.387(3) . ?
C18 H18 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C17 H17 0.9500 . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C12 C11 1.392(3) . ?
C12 H12 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C10 C9 1.382(3) . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C20 C21 1.396(3) . ?
C20 H20 0.9500 . ?
C11 H11 0.9500 . ?
C9 H9 0.9500 . ?
C24 C23 1.387(3) . ?
C24 H24 0.9500 . ?
C21 C22 1.379(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(4) . ?
C22 H22 0.9500 . ?
C23 H23 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 O3 114.35(8) . . ?
O1 P1 O2 114.55(7) . . ?
O3 P1 O2 105.42(7) . . ?
O1 P1 C19 115.81(9) . . ?
O3 P1 C19 102.90(8) . . ?
O2 P1 C19 102.29(8) . . ?
C1 O2 P1 122.91(12) . . ?
C6 O3 P1 117.01(12) . . ?
C1 C2 C5 136.42(17) . . ?
C1 C2 C3 134.12(17) . . ?
C5 C2 C3 89.46(15) . . ?
C2 C1 O2 120.67(16) . . ?
C2 C1 C7 127.23(16) . . ?
O2 C1 C7 112.09(15) . . ?
C24 C19 C20 119.97(19) . . ?
C24 C19 P1 121.72(16) . . ?
C20 C19 P1 118.24(15) . . ?
C15 C14 C13 120.51(18) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C4 C5 C2 92.86(16) . . ?
C4 C5 C6 134.43(17) . . ?
C2 C5 C6 132.71(17) . . ?
C5 C4 C13 135.49(18) . . ?
C5 C4 C3 93.70(15) . . ?
C13 C4 C3 130.80(16) . . ?
C14 C13 C18 118.99(17) . . ?
C14 C13 C4 119.45(16) . . ?
C18 C13 C4 121.56(17) . . ?
C14 C15 C16 119.93(18) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.24(18) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C8 C7 C12 118.07(17) . . ?
C8 C7 C1 120.50(16) . . ?
C12 C7 C1 121.42(17) . . ?
C17 C18 C13 120.22(18) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C4 C3 C2 83.99(14) . . ?
C4 C3 H3A 114.6 . . ?
C2 C3 H3A 114.6 . . ?
C4 C3 H3B 114.6 . . ?
C2 C3 H3B 114.6 . . ?
H3A C3 H3B 111.7 . . ?
C18 C17 C16 120.11(18) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C9 C8 C7 120.66(18) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C11 C12 C7 120.61(19) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
O3 C6 C5 111.10(16) . . ?
O3 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
O3 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C9 C10 C11 119.26(19) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C10 C9 C8 120.77(19) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C23 C24 C19 119.5(2) . . ?
C23 C24 H24 120.2 . . ?
C19 C24 H24 120.2 . . ?
C22 C21 C20 119.6(2) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.5(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?

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 O2 C1 59.09(15) . . . . ?
O3 P1 O2 C1 -67.51(14) . . . . ?
C19 P1 O2 C1 -174.79(13) . . . . ?
O1 P1 O3 C6 -35.61(15) . . . . ?
O2 P1 O3 C6 91.11(14) . . . . ?
C19 P1 O3 C6 -162.05(13) . . . . ?
C5 C2 C1 O2 2.1(3) . . . . ?
C3 C2 C1 O2 -177.41(17) . . . . ?
C5 C2 C1 C7 -176.69(19) . . . . ?
C3 C2 C1 C7 3.8(3) . . . . ?
P1 O2 C1 C2 24.7(2) . . . . ?
P1 O2 C1 C7 -156.36(12) . . . . ?
O1 P1 C19 C24 172.88(16) . . . . ?
O3 P1 C19 C24 -61.62(18) . . . . ?
O2 P1 C19 C24 47.59(18) . . . . ?
O1 P1 C19 C20 -10.07(19) . . . . ?
O3 P1 C19 C20 115.43(16) . . . . ?
O2 P1 C19 C20 -135.36(15) . . . . ?
C1 C2 C5 C4 -179.2(2) . . . . ?
C3 C2 C5 C4 0.43(15) . . . . ?
C1 C2 C5 C6 1.5(4) . . . . ?
C3 C2 C5 C6 -178.9(2) . . . . ?
C2 C5 C4 C13 -179.1(2) . . . . ?
C6 C5 C4 C13 0.2(4) . . . . ?
C2 C5 C4 C3 -0.43(15) . . . . ?
C6 C5 C4 C3 178.9(2) . . . . ?
C15 C14 C13 C18 0.0(3) . . . . ?
C15 C14 C13 C4 -179.08(17) . . . . ?
C5 C4 C13 C14 166.2(2) . . . . ?
C3 C4 C13 C14 -12.1(3) . . . . ?
C5 C4 C13 C18 -12.9(3) . . . . ?
C3 C4 C13 C18 168.81(18) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C2 C1 C7 C8 -158.90(18) . . . . ?
O2 C1 C7 C8 22.3(2) . . . . ?
C2 C1 C7 C12 21.5(3) . . . . ?
O2 C1 C7 C12 -157.33(17) . . . . ?
C14 C13 C18 C17 0.3(3) . . . . ?
C4 C13 C18 C17 179.42(17) . . . . ?
C5 C4 C3 C2 0.41(14) . . . . ?
C13 C4 C3 C2 179.22(19) . . . . ?
C1 C2 C3 C4 179.3(2) . . . . ?
C5 C2 C3 C4 -0.38(13) . . . . ?
C13 C18 C17 C16 -0.2(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C12 C7 C8 C9 -0.9(3) . . . . ?
C1 C7 C8 C9 179.49(18) . . . . ?
C8 C7 C12 C11 0.7(3) . . . . ?
C1 C7 C12 C11 -179.71(19) . . . . ?
P1 O3 C6 C5 -58.8(2) . . . . ?
C4 C5 C6 O3 -167.7(2) . . . . ?
C2 C5 C6 O3 11.3(3) . . . . ?
C24 C19 C20 C21 0.1(3) . . . . ?
P1 C19 C20 C21 -177.00(16) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C7 C12 C11 C10 0.0(3) . . . . ?
C11 C10 C9 C8 0.3(3) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C20 C19 C24 C23 0.4(3) . . . . ?
P1 C19 C24 C23 177.42(18) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C24 1.0(4) . . . . ?
C19 C24 C23 C22 -1.0(4) . . . . ?

_refine_diff_density_max         0.499
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_g807
_database_code_depnum_ccdc_archive 'CCDC 2005768'
loop_
_audit_author_name
_audit_author_address
'Qijian Ni'
;Anhui Normal University
China
;
_audit_update_record             
;
2020-05-26 deposited with the CCDC.	2020-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 O3 P'
_chemical_formula_sum            'C24 H21 O3 P'
_chemical_formula_weight         388.38

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           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

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

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

_cell_length_a                   6.2565(10)
_cell_length_b                   9.4325(10)
_cell_length_c                   16.395(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.178(4)
_cell_angle_gamma                90
_cell_volume                     961.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2050
_cell_measurement_theta_min      2.495
_cell_measurement_theta_max      30.587

_exptl_crystal_description       'prism frag'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.134
_exptl_absorpt_coefficient_mu    0.166
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   Sadabs
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33800
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.495
_diffrn_reflns_theta_max         30.587
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5781
_reflns_number_gt                5652
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.957
_reflns_Friedel_fraction_max     0.959
_reflns_Friedel_fraction_full    0.990

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

_computing_data_collection       'APEX3 v2016.5.0'
_computing_cell_refinement       
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2016.5.0'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.1011P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2671 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5781
_refine_ls_number_parameters     254
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0685
_refine_ls_wR_factor_gt          0.0678
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.58069(4) 0.10198(3) -0.08280(2) 0.01026(8) Uani 1 1 d . . . . .
O1 O 0.55759(17) 0.19958(11) -0.00443(6) 0.01293(19) Uani 1 1 d . . . . .
O2 O 0.34445(17) 0.05373(11) -0.11505(6) 0.0138(2) Uani 1 1 d . . . . .
O3 O 0.73445(17) -0.01486(11) -0.06633(7) 0.0158(2) Uani 1 1 d . . . . .
C1 C 0.5372(2) 0.13469(15) 0.07243(8) 0.0118(2) Uani 1 1 d . . . . .
C2 C 0.3758(2) 0.04387(14) 0.07713(8) 0.0125(2) Uani 1 1 d . . . . .
C3 C 0.2971(2) -0.05228(16) 0.14196(9) 0.0162(3) Uani 1 1 d . . . . .
H3A H 0.2376 -0.0006 0.1870 0.019 Uiso 1 1 calc R U . . .
H3B H 0.4040 -0.1238 0.1639 0.019 Uiso 1 1 calc R U . . .
C4 C 0.1214(2) -0.11202(15) 0.07558(9) 0.0137(3) Uani 1 1 d . . . . .
H4 H -0.0261 -0.0893 0.0899 0.016 Uiso 1 1 calc R U . . .
C5 C 0.1961(2) -0.00065(14) 0.01279(8) 0.0123(2) Uani 1 1 d . . . . .
H5 H 0.0875 0.0770 0.0033 0.015 Uiso 1 1 calc R U . . .
C6 C 0.2523(2) -0.05841(15) -0.06818(8) 0.0137(2) Uani 1 1 d . . . . .
H6A H 0.3570 -0.1368 -0.0582 0.016 Uiso 1 1 calc R U . . .
H6B H 0.1213 -0.0965 -0.1000 0.016 Uiso 1 1 calc R U . . .
C7 C 0.6413(2) 0.22662(15) -0.15792(8) 0.0132(2) Uani 1 1 d . . . . .
C8 C 0.8309(3) 0.20926(18) -0.19466(10) 0.0201(3) Uani 1 1 d . . . . .
H8 H 0.9267 0.1339 -0.1781 0.024 Uiso 1 1 calc R U . . .
C9 C 0.8785(3) 0.3032(2) -0.25568(11) 0.0265(4) Uani 1 1 d . . . . .
H9 H 1.0074 0.2921 -0.2808 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7386(3) 0.4127(2) -0.27986(11) 0.0285(4) Uani 1 1 d . . . . .
H10 H 0.7710 0.4755 -0.3221 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5521(3) 0.43126(19) -0.24290(11) 0.0280(4) Uani 1 1 d . . . . .
H11 H 0.4580 0.5076 -0.2593 0.034 Uiso 1 1 calc R U . . .
C12 C 0.5017(3) 0.33857(17) -0.18180(10) 0.0198(3) Uani 1 1 d . . . . .
H12 H 0.3735 0.3512 -0.1565 0.024 Uiso 1 1 calc R U . . .
C13 C 0.7019(2) 0.18230(14) 0.13711(8) 0.0126(2) Uani 1 1 d . . . . .
C14 C 0.8899(2) 0.24636(15) 0.11657(9) 0.0149(3) Uani 1 1 d . . . . .
H14 H 0.9100 0.2594 0.0605 0.018 Uiso 1 1 calc R U . . .
C15 C 1.0485(3) 0.29139(16) 0.17715(10) 0.0184(3) Uani 1 1 d . . . . .
H15 H 1.1769 0.3331 0.1622 0.022 Uiso 1 1 calc R U . . .
C16 C 1.0192(3) 0.27545(17) 0.25913(10) 0.0200(3) Uani 1 1 d . . . . .
H16 H 1.1270 0.3064 0.3006 0.024 Uiso 1 1 calc R U . . .
C17 C 0.8310(3) 0.21386(17) 0.28052(9) 0.0195(3) Uani 1 1 d . . . . .
H17 H 0.8095 0.2042 0.3367 0.023 Uiso 1 1 calc R U . . .
C18 C 0.6738(2) 0.16631(16) 0.22011(9) 0.0163(3) Uani 1 1 d . . . . .
H18 H 0.5470 0.1228 0.2353 0.020 Uiso 1 1 calc R U . . .
C19 C 0.1353(2) -0.26417(15) 0.04864(9) 0.0141(3) Uani 1 1 d . . . . .
C20 C -0.0473(2) -0.32732(16) 0.00719(9) 0.0175(3) Uani 1 1 d . . . . .
H20 H -0.1795 -0.2769 0.0012 0.021 Uiso 1 1 calc R U . . .
C21 C -0.0377(3) -0.46342(17) -0.02548(11) 0.0224(3) Uani 1 1 d . . . . .
H21 H -0.1628 -0.5049 -0.0538 0.027 Uiso 1 1 calc R U . . .
C22 C 0.1544(3) -0.53837(17) -0.01669(11) 0.0233(3) Uani 1 1 d . . . . .
H22 H 0.1612 -0.6311 -0.0389 0.028 Uiso 1 1 calc R U . . .
C23 C 0.3362(3) -0.47720(17) 0.02465(11) 0.0235(3) Uani 1 1 d . . . . .
H23 H 0.4677 -0.5284 0.0311 0.028 Uiso 1 1 calc R U . . .
C24 C 0.3268(3) -0.34094(17) 0.05671(10) 0.0193(3) Uani 1 1 d . . . . .
H24 H 0.4528 -0.2997 0.0845 0.023 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 O3 1.4687(11) . ?
P1 O2 1.5821(11) . ?
P1 O1 1.5998(11) . ?
P1 C7 1.7730(14) . ?
O1 C1 1.4189(16) . ?
O2 C6 1.4620(17) . ?
C1 C2 1.3331(19) . ?
C1 C13 1.4672(18) . ?
C2 C5 1.5156(19) . ?
C2 C3 1.5190(19) . ?
C3 C4 1.566(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C19 1.5068(19) . ?
C4 C5 1.5763(19) . ?
C4 H4 1.0000 . ?
C5 C6 1.5110(19) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.397(2) . ?
C7 C12 1.399(2) . ?
C8 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.395(2) . ?
C13 C18 1.3990(19) . ?
C14 C15 1.392(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.394(2) . ?
C19 C20 1.398(2) . ?
C20 C21 1.395(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(2) . ?
C23 H23 0.9500 . ?
C24 H24 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
O3 P1 O2 114.55(6) . . ?
O3 P1 O1 113.46(6) . . ?
O2 P1 O1 105.79(6) . . ?
O3 P1 C7 116.14(7) . . ?
O2 P1 C7 102.74(6) . . ?
O1 P1 C7 102.76(6) . . ?
C1 O1 P1 119.31(9) . . ?
C6 O2 P1 116.08(9) . . ?
C2 C1 O1 118.00(12) . . ?
C2 C1 C13 129.25(13) . . ?
O1 C1 C13 112.74(12) . . ?
C1 C2 C5 130.37(13) . . ?
C1 C2 C3 136.79(13) . . ?
C5 C2 C3 92.84(11) . . ?
C2 C3 C4 89.12(10) . . ?
C2 C3 H3A 113.8 . . ?
C4 C3 H3A 113.8 . . ?
C2 C3 H3B 113.8 . . ?
C4 C3 H3B 113.8 . . ?
H3A C3 H3B 111.0 . . ?
C19 C4 C3 119.22(12) . . ?
C19 C4 C5 114.39(11) . . ?
C3 C4 C5 88.79(10) . . ?
C19 C4 H4 110.9 . . ?
C3 C4 H4 110.9 . . ?
C5 C4 H4 110.9 . . ?
C6 C5 C2 119.09(12) . . ?
C6 C5 C4 116.53(11) . . ?
C2 C5 C4 88.85(10) . . ?
C6 C5 H5 110.2 . . ?
C2 C5 H5 110.2 . . ?
C4 C5 H5 110.2 . . ?
O2 C6 C5 110.07(11) . . ?
O2 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
O2 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C12 120.08(14) . . ?
C8 C7 P1 118.48(12) . . ?
C12 C7 P1 121.42(12) . . ?
C9 C8 C7 119.50(16) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.22(17) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.43(16) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 120.21(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 119.54(16) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C14 C13 C18 118.61(12) . . ?
C14 C13 C1 120.19(12) . . ?
C18 C13 C1 121.19(13) . . ?
C15 C14 C13 120.95(14) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 120.06(15) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.62(14) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.47(14) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.28(14) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C24 C19 C20 118.27(14) . . ?
C24 C19 C4 122.89(13) . . ?
C20 C19 C4 118.59(13) . . ?
C21 C20 C19 120.83(14) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 120.06(15) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 119.64(15) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.23(16) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 120.96(15) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 P1 O1 C1 -45.34(12) . . . . ?
O2 P1 O1 C1 81.06(11) . . . . ?
C7 P1 O1 C1 -171.54(10) . . . . ?
O3 P1 O2 C6 49.13(11) . . . . ?
O1 P1 O2 C6 -76.60(10) . . . . ?
C7 P1 O2 C6 175.99(10) . . . . ?
P1 O1 C1 C2 -57.05(16) . . . . ?
P1 O1 C1 C13 124.04(11) . . . . ?
O1 C1 C2 C5 -2.7(2) . . . . ?
C13 C1 C2 C5 175.96(13) . . . . ?
O1 C1 C2 C3 176.84(15) . . . . ?
C13 C1 C2 C3 -4.5(3) . . . . ?
C1 C2 C3 C4 -174.79(17) . . . . ?
C5 C2 C3 C4 4.89(11) . . . . ?
C2 C3 C4 C19 112.78(13) . . . . ?
C2 C3 C4 C5 -4.70(10) . . . . ?
C1 C2 C5 C6 54.9(2) . . . . ?
C3 C2 C5 C6 -124.86(13) . . . . ?
C1 C2 C5 C4 174.86(15) . . . . ?
C3 C2 C5 C4 -4.86(11) . . . . ?
C19 C4 C5 C6 5.18(17) . . . . ?
C3 C4 C5 C6 126.95(13) . . . . ?
C19 C4 C5 C2 -117.06(13) . . . . ?
C3 C4 C5 C2 4.71(10) . . . . ?
P1 O2 C6 C5 72.69(13) . . . . ?
C2 C5 C6 O2 -68.08(16) . . . . ?
C4 C5 C6 O2 -172.68(11) . . . . ?
O3 P1 C7 C8 -1.78(14) . . . . ?
O2 P1 C7 C8 -127.61(12) . . . . ?
O1 P1 C7 C8 122.68(12) . . . . ?
O3 P1 C7 C12 176.83(12) . . . . ?
O2 P1 C7 C12 51.00(13) . . . . ?
O1 P1 C7 C12 -58.71(13) . . . . ?
C12 C7 C8 C9 -0.7(2) . . . . ?
P1 C7 C8 C9 177.96(13) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C7 0.1(3) . . . . ?
C8 C7 C12 C11 0.7(2) . . . . ?
P1 C7 C12 C11 -177.89(13) . . . . ?
C2 C1 C13 C14 162.31(15) . . . . ?
O1 C1 C13 C14 -18.93(18) . . . . ?
C2 C1 C13 C18 -18.4(2) . . . . ?
O1 C1 C13 C18 160.33(12) . . . . ?
C18 C13 C14 C15 1.1(2) . . . . ?
C1 C13 C14 C15 -179.61(13) . . . . ?
C13 C14 C15 C16 -1.3(2) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C16 C17 C18 1.0(2) . . . . ?
C16 C17 C18 C13 -1.1(2) . . . . ?
C14 C13 C18 C17 0.1(2) . . . . ?
C1 C13 C18 C17 -179.18(13) . . . . ?
C3 C4 C19 C24 -22.8(2) . . . . ?
C5 C4 C19 C24 80.35(17) . . . . ?
C3 C4 C19 C20 163.08(13) . . . . ?
C5 C4 C19 C20 -93.80(15) . . . . ?
C24 C19 C20 C21 -0.2(2) . . . . ?
C4 C19 C20 C21 174.20(14) . . . . ?
C19 C20 C21 C22 0.3(2) . . . . ?
C20 C21 C22 C23 0.0(2) . . . . ?
C21 C22 C23 C24 -0.5(2) . . . . ?
C22 C23 C24 C19 0.6(2) . . . . ?
C20 C19 C24 C23 -0.3(2) . . . . ?
C4 C19 C24 C23 -174.42(14) . . . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_g546
_database_code_depnum_ccdc_archive 'CCDC 2005766'
loop_
_audit_author_name
_audit_author_address
'Qijian Ni'
;Anhui Normal University
China
;
_audit_update_record             
;
2020-05-26 deposited with the CCDC.	2020-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 O3 P'
_chemical_formula_sum            'C12 H11 O3 P'
_chemical_formula_weight         234.18

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                   8.145(3)
_cell_length_b                   13.268(4)
_cell_length_c                   10.374(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.850(10)
_cell_angle_gamma                90
_cell_volume                     1061.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1098
_cell_measurement_theta_min      2.581
_cell_measurement_theta_max      30.555

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.246
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   Sadabs
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11289
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.581
_diffrn_reflns_theta_max         30.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3235
_reflns_number_gt                2751
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 v2016.6.0'
_computing_cell_refinement       
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2016.6.0'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0386P)²+0.5991P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3235
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.48031(4) 0.12220(2) 0.33932(3) 0.01072(8) Uani 1 1 d . . . . .
O1 O 0.61480(11) 0.16416(7) 0.45761(9) 0.01581(19) Uani 1 1 d . . . . .
O2 O 0.49618(11) 0.00265(6) 0.34290(9) 0.01307(18) Uani 1 1 d . . . . .
O3 O 0.50888(11) 0.16275(7) 0.20341(9) 0.01347(18) Uani 1 1 d . . . . .
C1 C 0.38386(16) -0.06351(9) 0.24999(13) 0.0137(2) Uani 1 1 d . . . . .
H1 H 0.3579 -0.1269 0.2814 0.016 Uiso 1 1 calc R U . . .
C2 C 0.31283(16) -0.04004(9) 0.11938(13) 0.0130(2) Uani 1 1 d . . . . .
C3 C 0.19576(17) -0.09427(10) -0.00682(13) 0.0164(2) Uani 1 1 d . . . . .
H3A H 0.0770 -0.1073 -0.0047 0.020 Uiso 1 1 calc R U . . .
H3B H 0.2476 -0.1560 -0.0308 0.020 Uiso 1 1 calc R U . . .
C4 C 0.21048(17) 0.00076(9) -0.09228(13) 0.0165(2) Uani 1 1 d . . . . .
H4A H 0.2705 -0.0122 -0.1598 0.020 Uiso 1 1 calc R U . . .
H4B H 0.0991 0.0362 -0.1345 0.020 Uiso 1 1 calc R U . . .
C5 C 0.32544(16) 0.04921(9) 0.03938(12) 0.0131(2) Uani 1 1 d . . . . .
C6 C 0.40756(16) 0.13668(9) 0.07079(12) 0.0140(2) Uani 1 1 d . . . . .
H6 H 0.3971 0.1840 -0.0002 0.017 Uiso 1 1 calc R U . . .
C7 C 0.26214(15) 0.15215(9) 0.32481(12) 0.0120(2) Uani 1 1 d . . . . .
C8 C 0.17962(16) 0.23515(9) 0.24760(13) 0.0149(2) Uani 1 1 d . . . . .
H8 H 0.2352 0.2715 0.1945 0.018 Uiso 1 1 calc R U . . .
C9 C 0.01617(16) 0.26428(10) 0.24880(14) 0.0175(3) Uani 1 1 d . . . . .
H9 H -0.0407 0.3202 0.1958 0.021 Uiso 1 1 calc R U . . .
C10 C -0.06383(16) 0.21157(10) 0.32755(14) 0.0180(3) Uani 1 1 d . . . . .
H10 H -0.1747 0.2323 0.3295 0.022 Uiso 1 1 calc R U . . .
C11 C 0.01721(17) 0.12870(10) 0.40359(14) 0.0185(3) Uani 1 1 d . . . . .
H11 H -0.0388 0.0927 0.4567 0.022 Uiso 1 1 calc R U . . .
C12 C 0.17980(16) 0.09828(10) 0.40231(13) 0.0158(2) Uani 1 1 d . . . . .
H12 H 0.2347 0.0413 0.4537 0.019 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 1.4653(9) . ?
P1 O2 1.5910(10) . ?
P1 O3 1.5948(10) . ?
P1 C7 1.7792(14) . ?
O2 C1 1.4024(14) . ?
O3 C6 1.3999(15) . ?
C1 C2 1.3270(18) . ?
C1 H1 0.9500 . ?
C2 C5 1.4685(17) . ?
C2 C3 1.5278(17) . ?
C3 C4 1.5681(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5262(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.3266(17) . ?
C6 H6 0.9500 . ?
C7 C12 1.3984(18) . ?
C7 C8 1.3994(17) . ?
C8 C9 1.3902(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3895(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3886(19) . ?
C11 H11 0.9500 . ?
C12 H12 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 O2 109.03(5) . . ?
O1 P1 O3 109.21(6) . . ?
O2 P1 O3 108.85(5) . . ?
O1 P1 C7 116.23(6) . . ?
O2 P1 C7 107.22(5) . . ?
O3 P1 C7 106.08(5) . . ?
C1 O2 P1 125.31(8) . . ?
C6 O3 P1 125.27(8) . . ?
C2 C1 O2 121.82(11) . . ?
C2 C1 H1 119.1 . . ?
O2 C1 H1 119.1 . . ?
C1 C2 C5 132.78(11) . . ?
C1 C2 C3 135.22(12) . . ?
C5 C2 C3 91.94(10) . . ?
C2 C3 C4 88.01(9) . . ?
C2 C3 H3A 114.0 . . ?
C4 C3 H3A 114.0 . . ?
C2 C3 H3B 114.0 . . ?
C4 C3 H3B 114.0 . . ?
H3A C3 H3B 111.2 . . ?
C5 C4 C3 88.25(9) . . ?
C5 C4 H4A 113.9 . . ?
C3 C4 H4A 113.9 . . ?
C5 C4 H4B 113.9 . . ?
C3 C4 H4B 113.9 . . ?
H4A C4 H4B 111.1 . . ?
C6 C5 C2 133.51(11) . . ?
C6 C5 C4 134.68(12) . . ?
C2 C5 C4 91.80(10) . . ?
C5 C6 O3 123.22(11) . . ?
C5 C6 H6 118.4 . . ?
O3 C6 H6 118.4 . . ?
C12 C7 C8 120.03(12) . . ?
C12 C7 P1 119.26(9) . . ?
C8 C7 P1 120.40(10) . . ?
C9 C8 C7 119.86(12) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 119.90(12) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.39(12) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.27(13) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 119.54(12) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?

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
O1 P1 O2 C1 176.58(10) . . . . ?
O3 P1 O2 C1 -64.37(11) . . . . ?
C7 P1 O2 C1 49.97(11) . . . . ?
O1 P1 O3 C6 178.43(9) . . . . ?
O2 P1 O3 C6 59.50(10) . . . . ?
C7 P1 O3 C6 -55.59(11) . . . . ?
P1 O2 C1 C2 35.01(17) . . . . ?
O2 C1 C2 C5 0.1(2) . . . . ?
O2 C1 C2 C3 176.55(13) . . . . ?
C1 C2 C3 C4 -176.99(16) . . . . ?
C5 C2 C3 C4 0.39(10) . . . . ?
C2 C3 C4 C5 -0.38(9) . . . . ?
C1 C2 C5 C6 -2.1(3) . . . . ?
C3 C2 C5 C6 -179.55(15) . . . . ?
C1 C2 C5 C4 177.08(15) . . . . ?
C3 C2 C5 C4 -0.40(10) . . . . ?
C3 C4 C5 C6 179.52(15) . . . . ?
C3 C4 C5 C2 0.39(10) . . . . ?
C2 C5 C6 O3 -0.5(2) . . . . ?
C4 C5 C6 O3 -179.32(13) . . . . ?
P1 O3 C6 C5 -28.48(17) . . . . ?
O1 P1 C7 C12 -80.02(11) . . . . ?
O2 P1 C7 C12 42.21(11) . . . . ?
O3 P1 C7 C12 158.40(10) . . . . ?
O1 P1 C7 C8 93.53(11) . . . . ?
O2 P1 C7 C8 -144.25(10) . . . . ?
O3 P1 C7 C8 -28.06(11) . . . . ?
C12 C7 C8 C9 0.40(18) . . . . ?
P1 C7 C8 C9 -173.10(9) . . . . ?
C7 C8 C9 C10 0.63(19) . . . . ?
C8 C9 C10 C11 -1.1(2) . . . . ?
C9 C10 C11 C12 0.5(2) . . . . ?
C10 C11 C12 C7 0.5(2) . . . . ?
C8 C7 C12 C11 -0.97(19) . . . . ?
P1 C7 C12 C11 172.59(10) . . . . ?

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
C12 H12 O2 0.95 2.57 3.3523(17) 139.8 3_656

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_g766
_database_code_depnum_ccdc_archive 'CCDC 2005767'
loop_
_audit_author_name
_audit_author_address
'Qijian Ni'
;Anhui Normal University
China
;
_audit_update_record             
;
2020-05-26 deposited with the CCDC.	2020-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H23 O3 P'
_chemical_formula_sum            'C26 H23 O3 P'
_chemical_formula_weight         414.41

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                   14.668(5)
_cell_length_b                   13.512(4)
_cell_length_c                   10.815(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.316(9)
_cell_angle_gamma                90
_cell_volume                     2141.7(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1151
_cell_measurement_theta_min      2.413
_cell_measurement_theta_max      30.182

_exptl_crystal_description       'PRISM FRAG'
_exptl_crystal_colour            'LIGHT YELLOW'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.153
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31655
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.413
_diffrn_reflns_theta_max         30.182
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6290
_reflns_number_gt                4671
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 v2016.5.0'
_computing_cell_refinement       
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2016.5.0'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.9664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6290
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.73910(2) 0.52309(3) 0.48897(3) 0.01207(9) Uani 1 1 d . . . . .
O1 O 0.79512(7) 0.62488(7) 0.49514(9) 0.0151(2) Uani 1 1 d . . . . .
O2 O 0.71908(7) 0.49632(7) 0.62713(9) 0.0135(2) Uani 1 1 d . . . . .
O3 O 0.65932(7) 0.52452(7) 0.40314(9) 0.0159(2) Uani 1 1 d . . . . .
C1 C 0.76270(10) 0.71298(10) 0.54922(12) 0.0127(3) Uani 1 1 d . . . . .
C2 C 0.63582(9) 0.53009(10) 0.68475(12) 0.0126(3) Uani 1 1 d . . . . .
H2 H 0.5811 0.5055 0.6360 0.015 Uiso 1 1 calc R U . . .
C3 C 0.63562(9) 0.64118(10) 0.68660(12) 0.0123(3) Uani 1 1 d . . . . .
C4 C 0.69595(10) 0.71318(10) 0.63021(12) 0.0126(3) Uani 1 1 d . . . . .
C5 C 0.64441(10) 0.79687(10) 0.69499(12) 0.0128(3) Uani 1 1 d . . . . .
H5 H 0.6826 0.8271 0.7638 0.015 Uiso 1 1 calc R U . . .
C6 C 0.58540(10) 0.71247(10) 0.74155(12) 0.0127(3) Uani 1 1 d . . . . .
C7 C 0.50554(10) 0.71725(10) 0.81721(12) 0.0127(3) Uani 1 1 d . . . . .
C8 C 0.49408(10) 0.79989(10) 0.89399(12) 0.0144(3) Uani 1 1 d . . . . .
H8 H 0.5368 0.8527 0.8930 0.017 Uiso 1 1 calc R U . . .
C9 C 0.42077(11) 0.80494(11) 0.97133(13) 0.0175(3) Uani 1 1 d . . . . .
H9 H 0.4140 0.8607 1.0236 0.021 Uiso 1 1 calc R U . . .
C10 C 0.35733(11) 0.72858(11) 0.97234(14) 0.0198(3) Uani 1 1 d . . . . .
H10 H 0.3074 0.7320 1.0254 0.024 Uiso 1 1 calc R U . . .
C11 C 0.36729(10) 0.64708(11) 0.89527(14) 0.0185(3) Uani 1 1 d . . . . .
H11 H 0.3238 0.5950 0.8957 0.022 Uiso 1 1 calc R U . . .
C12 C 0.44041(10) 0.64144(10) 0.81768(13) 0.0151(3) Uani 1 1 d . . . . .
H12 H 0.4462 0.5859 0.7647 0.018 Uiso 1 1 calc R U . . .
C13 C 0.81100(9) 0.80097(10) 0.50426(13) 0.0133(3) Uani 1 1 d . . . . .
C14 C 0.84312(10) 0.80308(11) 0.38383(13) 0.0160(3) Uani 1 1 d . . . . .
H14 H 0.8360 0.7464 0.3324 0.019 Uiso 1 1 calc R U . . .
C15 C 0.88527(11) 0.88712(11) 0.33901(14) 0.0204(3) Uani 1 1 d . . . . .
H15 H 0.9060 0.8878 0.2569 0.024 Uiso 1 1 calc R U . . .
C16 C 0.89722(11) 0.96973(12) 0.41347(16) 0.0228(3) Uani 1 1 d . . . . .
H16 H 0.9260 1.0271 0.3827 0.027 Uiso 1 1 calc R U . . .
C17 C 0.86686(11) 0.96839(11) 0.53372(15) 0.0217(3) Uani 1 1 d . . . . .
H17 H 0.8752 1.0250 0.5850 0.026 Uiso 1 1 calc R U . . .
C18 C 0.82449(10) 0.88474(11) 0.57913(14) 0.0180(3) Uani 1 1 d . . . . .
H18 H 0.8045 0.8843 0.6616 0.022 Uiso 1 1 calc R U . . .
C19 C 0.82541(10) 0.43559(11) 0.45336(13) 0.0162(3) Uani 1 1 d . . . . .
C20 C 0.81175(13) 0.37523(13) 0.35079(16) 0.0282(4) Uani 1 1 d . . . . .
H20 H 0.7592 0.3841 0.2976 0.034 Uiso 1 1 calc R U . . .
C21 C 0.87473(14) 0.30164(14) 0.32541(19) 0.0397(5) Uani 1 1 d . . . . .
H21 H 0.8651 0.2602 0.2551 0.048 Uiso 1 1 calc R U . . .
C22 C 0.95092(13) 0.28897(13) 0.4023(2) 0.0357(5) Uani 1 1 d . . . . .
H22 H 0.9940 0.2389 0.3849 0.043 Uiso 1 1 calc R U . . .
C23 C 0.96476(13) 0.34875(14) 0.5045(2) 0.0399(5) Uani 1 1 d . . . . .
H23 H 1.0173 0.3396 0.5576 0.048 Uiso 1 1 calc R U . . .
C24 C 0.90238(12) 0.42219(13) 0.53011(18) 0.0321(4) Uani 1 1 d . . . . .
H24 H 0.9124 0.4635 0.6005 0.039 Uiso 1 1 calc R U . . .
C25 C 0.63872(10) 0.48402(11) 0.81281(13) 0.0169(3) Uani 1 1 d . . . . .
H25A H 0.6371 0.4118 0.8053 0.025 Uiso 1 1 calc R U . . .
H25B H 0.5859 0.5065 0.8579 0.025 Uiso 1 1 calc R U . . .
H25C H 0.6950 0.5040 0.8580 0.025 Uiso 1 1 calc R U . . .
C26 C 0.59629(10) 0.87516(10) 0.61616(13) 0.0156(3) Uani 1 1 d . . . . .
H26A H 0.5562 0.8431 0.5535 0.023 Uiso 1 1 calc R U . . .
H26B H 0.6417 0.9155 0.5753 0.023 Uiso 1 1 calc R U . . .
H26C H 0.5599 0.9175 0.6687 0.023 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 O3 1.4641(11) . ?
P1 O2 1.5764(11) . ?
P1 O1 1.6020(11) . ?
P1 C19 1.7855(15) . ?
O1 C1 1.4170(16) . ?
O2 C2 1.4661(16) . ?
C1 C4 1.340(2) . ?
C1 C13 1.4764(19) . ?
C2 C3 1.5011(19) . ?
C2 C25 1.5175(19) . ?
C2 H2 1.0000 . ?
C3 C6 1.3635(19) . ?
C3 C4 1.4646(19) . ?
C4 C5 1.5439(19) . ?
C5 C26 1.5151(19) . ?
C5 C6 1.5291(19) . ?
C5 H5 1.0000 . ?
C6 C7 1.4571(19) . ?
C7 C12 1.401(2) . ?
C7 C8 1.4056(19) . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.401(2) . ?
C13 C14 1.403(2) . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.385(2) . ?
C19 C24 1.386(2) . ?
C20 C21 1.392(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.378(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 P1 O2 115.42(6) . . ?
O3 P1 O1 114.23(6) . . ?
O2 P1 O1 105.80(5) . . ?
O3 P1 C19 115.31(7) . . ?
O2 P1 C19 102.32(6) . . ?
O1 P1 C19 102.15(7) . . ?
C1 O1 P1 123.94(9) . . ?
C2 O2 P1 121.45(8) . . ?
C4 C1 O1 122.54(12) . . ?
C4 C1 C13 125.93(12) . . ?
O1 C1 C13 111.53(11) . . ?
O2 C2 C3 108.60(11) . . ?
O2 C2 C25 105.50(11) . . ?
C3 C2 C25 113.45(11) . . ?
O2 C2 H2 109.7 . . ?
C3 C2 H2 109.7 . . ?
C25 C2 H2 109.7 . . ?
C6 C3 C4 93.34(11) . . ?
C6 C3 C2 135.53(13) . . ?
C4 C3 C2 131.08(12) . . ?
C1 C4 C3 137.78(13) . . ?
C1 C4 C5 133.02(12) . . ?
C3 C4 C5 88.99(11) . . ?
C26 C5 C6 116.68(12) . . ?
C26 C5 C4 118.78(11) . . ?
C6 C5 C4 84.11(10) . . ?
C26 C5 H5 111.5 . . ?
C6 C5 H5 111.5 . . ?
C4 C5 H5 111.5 . . ?
C3 C6 C7 137.46(13) . . ?
C3 C6 C5 93.46(11) . . ?
C7 C6 C5 129.08(12) . . ?
C12 C7 C8 118.74(13) . . ?
C12 C7 C6 122.24(12) . . ?
C8 C7 C6 119.01(13) . . ?
C9 C8 C7 120.54(13) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 120.17(13) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.73(13) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.45(14) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 120.33(13) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C18 C13 C14 118.37(13) . . ?
C18 C13 C1 121.24(13) . . ?
C14 C13 C1 120.38(12) . . ?
C15 C14 C13 120.75(14) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 120.26(14) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.72(14) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.37(14) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 120.52(14) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C20 C19 C24 119.40(15) . . ?
C20 C19 P1 118.81(12) . . ?
C24 C19 P1 121.65(12) . . ?
C19 C20 C21 120.19(17) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.91(17) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.12(16) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 120.21(18) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 120.17(17) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
C2 C25 H25A 109.5 . . ?
C2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C5 C26 H26A 109.5 . . ?
C5 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C5 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 P1 O1 C1 70.58(12) . . . . ?
O2 P1 O1 C1 -57.49(11) . . . . ?
C19 P1 O1 C1 -164.22(11) . . . . ?
O3 P1 O2 C2 -36.83(12) . . . . ?
O1 P1 O2 C2 90.53(10) . . . . ?
C19 P1 O2 C2 -162.86(10) . . . . ?
P1 O1 C1 C4 19.72(19) . . . . ?
P1 O1 C1 C13 -159.91(9) . . . . ?
P1 O2 C2 C3 -61.75(13) . . . . ?
P1 O2 C2 C25 176.30(9) . . . . ?
O2 C2 C3 C6 -168.88(15) . . . . ?
C25 C2 C3 C6 -51.9(2) . . . . ?
O2 C2 C3 C4 8.0(2) . . . . ?
C25 C2 C3 C4 124.93(15) . . . . ?
O1 C1 C4 C3 -2.2(3) . . . . ?
C13 C1 C4 C3 177.42(15) . . . . ?
O1 C1 C4 C5 -175.31(13) . . . . ?
C13 C1 C4 C5 4.3(3) . . . . ?
C6 C3 C4 C1 -172.55(18) . . . . ?
C2 C3 C4 C1 9.7(3) . . . . ?
C6 C3 C4 C5 2.45(11) . . . . ?
C2 C3 C4 C5 -175.34(15) . . . . ?
C1 C4 C5 C26 55.9(2) . . . . ?
C3 C4 C5 C26 -119.47(13) . . . . ?
C1 C4 C5 C6 173.22(16) . . . . ?
C3 C4 C5 C6 -2.19(10) . . . . ?
C4 C3 C6 C7 177.48(17) . . . . ?
C2 C3 C6 C7 -4.9(3) . . . . ?
C4 C3 C6 C5 -2.48(11) . . . . ?
C2 C3 C6 C5 175.14(16) . . . . ?
C26 C5 C6 C3 121.68(13) . . . . ?
C4 C5 C6 C3 2.36(10) . . . . ?
C26 C5 C6 C7 -58.28(19) . . . . ?
C4 C5 C6 C7 -177.60(14) . . . . ?
C3 C6 C7 C12 -22.7(3) . . . . ?
C5 C6 C7 C12 157.22(14) . . . . ?
C3 C6 C7 C8 156.19(16) . . . . ?
C5 C6 C7 C8 -23.9(2) . . . . ?
C12 C7 C8 C9 1.7(2) . . . . ?
C6 C7 C8 C9 -177.25(13) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 C7 0.7(2) . . . . ?
C8 C7 C12 C11 -1.7(2) . . . . ?
C6 C7 C12 C11 177.23(13) . . . . ?
C4 C1 C13 C18 30.9(2) . . . . ?
O1 C1 C13 C18 -149.46(13) . . . . ?
C4 C1 C13 C14 -147.89(15) . . . . ?
O1 C1 C13 C14 31.73(18) . . . . ?
C18 C13 C14 C15 -1.5(2) . . . . ?
C1 C13 C14 C15 177.30(13) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C16 C17 C18 C13 -0.6(2) . . . . ?
C14 C13 C18 C17 1.4(2) . . . . ?
C1 C13 C18 C17 -177.42(14) . . . . ?
O3 P1 C19 C20 -0.79(15) . . . . ?
O2 P1 C19 C20 125.32(13) . . . . ?
O1 P1 C19 C20 -125.28(13) . . . . ?
O3 P1 C19 C24 -176.41(13) . . . . ?
O2 P1 C19 C24 -50.30(15) . . . . ?
O1 P1 C19 C24 59.10(15) . . . . ?
C24 C19 C20 C21 0.2(3) . . . . ?
P1 C19 C20 C21 -175.53(14) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C22 C23 C24 C19 0.4(3) . . . . ?
C20 C19 C24 C23 -0.3(3) . . . . ?
P1 C19 C24 C23 175.31(15) . . . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2036801'
loop_
_audit_author_name
_audit_author_address
cyclobutent
;Anhui Normal University
China
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2020-10-16 downloaded from the CCDC.
;
_audit_creation_date             2020-10-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H25 O2 P Si'
_chemical_formula_sum            'C22 H25 O2 P Si'
_chemical_formula_weight         380.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.6855(10)
_cell_length_b                   11.4436(9)
_cell_length_c                   15.6122(11)
_cell_angle_alpha                90
_cell_angle_beta                 108.696(3)
_cell_angle_gamma                90
_cell_volume                     2146.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.278
_cell_measurement_theta_min      3.262
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1272 before and 0.0886 after correction. The Ratio of minimum to maximum transmission is 0.7292. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1434
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            83096
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.755
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2556
_reflns_number_total             3773
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3773
_refine_ls_number_restraints     617
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.192
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0822P)²+2.3815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1819
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-C1
 1.54 with sigma of 0.001
 Si1-C14A \\sim Si1-C14
 with sigma of 0.02
 Si1-C13 \\sim Si1-C13A
 with sigma of 0.02
 Si1-C15A \\sim Si1-C15
 with sigma of 0.02
3. Rigid bond restraints
 C19, C22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
C5 \\sim C6 \\sim C7 \\sim C2 \\sim C16 \\sim C12 \\sim C17 \\sim C4 \\sim C21
\\sim C1 \\sim C3 \\sim C8 \\sim C19 \\sim C18 \\sim C20 \\sim C11 \\sim C10
\\sim C9 \\sim C22 \\sim C13 \\sim C14 \\sim C15 \\sim C13A \\sim C14A \\sim
C15A: within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Si1) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(C15A) \\sim Ueq:
with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C22) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 Si1, C13, C14, C15, C13A, C14A, C15A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C14A)=Sof(H14D)=Sof(H14E)=
 Sof(H14F)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C1(H1A,H1B)
7.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C17(H17), C21(H21), C8(H8), C18(H18), C20(H20), C11(H11), C10(H10),
 C9(H9)
7.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C13A(H13D,H13E,H13F), C14A(H14D,H14E,H14F), C15A(H15D,H15E,H15F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.14324(7) 0.81320(8) 0.06283(6) 0.0496(3) Uani 1 1 d . . . . .
Si1 Si -0.34916(9) 0.73795(13) -0.04442(8) 0.0723(4) Uani 1 1 d D U . . .
O1 O 0.06474(19) 0.8320(2) 0.12336(16) 0.0595(7) Uani 1 1 d . . . . .
O2 O 0.1741(2) 0.9188(2) 0.02383(19) 0.0713(8) Uani 1 1 d . . . . .
C5 C -0.0370(3) 0.6991(3) -0.0302(2) 0.0460(8) Uani 1 1 d . U . . .
C6 C 0.0715(3) 0.7070(3) -0.0205(2) 0.0441(7) Uani 1 1 d . U . . .
C7 C 0.2595(3) 0.7443(3) 0.1439(2) 0.0489(8) Uani 1 1 d . U . . .
C2 C -0.1026(3) 0.7631(3) 0.0128(2) 0.0492(8) Uani 1 1 d D U . . .
C16 C 0.1280(3) 0.6443(3) -0.0761(2) 0.0463(8) Uani 1 1 d . U . . .
C12 C 0.3663(3) 0.7849(4) 0.1549(2) 0.0601(9) Uani 1 1 d . U . . .
H12 H 0.377190 0.846370 0.119697 0.072 Uiso 1 1 calc R . . . .
C17 C 0.0911(3) 0.5350(3) -0.1122(2) 0.0544(8) Uani 1 1 d . U . . .
H17 H 0.032294 0.499187 -0.099076 0.065 Uiso 1 1 calc R . . . .
C4 C -0.1444(3) 0.6406(3) -0.0889(2) 0.0549(9) Uani 1 1 d . U . . .
H4A H -0.149007 0.557596 -0.078091 0.066 Uiso 1 1 calc R . . . .
H4B H -0.164420 0.657986 -0.152938 0.066 Uiso 1 1 calc R . . . .
C21 C 0.2170(3) 0.6934(3) -0.0967(2) 0.0568(9) Uani 1 1 d . U . . .
H21 H 0.244656 0.765724 -0.072566 0.068 Uiso 1 1 calc R . . . .
C1 C -0.0536(3) 0.8559(3) 0.0859(2) 0.0585(9) Uani 1 1 d D U . . .
H1A H -0.065871 0.933630 0.059723 0.070 Uiso 1 1 calc R . . . .
H1B H -0.088457 0.851200 0.132771 0.070 Uiso 1 1 calc R . . . .
C3 C -0.2010(3) 0.7196(3) -0.0362(2) 0.0546(9) Uani 1 1 d . U . . .
C8 C 0.2454(3) 0.6523(3) 0.1966(2) 0.0605(9) Uani 1 1 d . U . . .
H8 H 0.174356 0.624025 0.189431 0.073 Uiso 1 1 calc R . . . .
C19 C 0.2289(3) 0.5287(4) -0.1886(3) 0.0681(10) Uani 1 1 d . U . . .
C18 C 0.1415(3) 0.4791(4) -0.1675(3) 0.0663(10) Uani 1 1 d . U . . .
H18 H 0.115517 0.406113 -0.191109 0.080 Uiso 1 1 calc R . . . .
C20 C 0.2647(3) 0.6358(4) -0.1527(3) 0.0652(10) Uani 1 1 d . U . . .
H20 H 0.323303 0.671260 -0.166499 0.078 Uiso 1 1 calc R . . . .
C11 C 0.4559(3) 0.7337(4) 0.2183(3) 0.0683(11) Uani 1 1 d . U . . .
H11 H 0.527268 0.761170 0.225787 0.082 Uiso 1 1 calc R . . . .
C10 C 0.4416(4) 0.6445(4) 0.2697(3) 0.0728(11) Uani 1 1 d . U . . .
H10 H 0.503238 0.611084 0.312267 0.087 Uiso 1 1 calc R . . . .
C9 C 0.3368(4) 0.6020(4) 0.2600(3) 0.0719(11) Uani 1 1 d . U . . .
H9 H 0.327458 0.540258 0.295691 0.086 Uiso 1 1 calc R . . . .
C22 C 0.2840(4) 0.4650(5) -0.2475(3) 0.0951(14) Uani 1 1 d . U . . .
H22A H 0.345970 0.420642 -0.210109 0.143 Uiso 1 1 calc GR . . . .
H22B H 0.309902 0.520639 -0.282270 0.143 Uiso 1 1 calc GR . . . .
H22C H 0.231343 0.413232 -0.287608 0.143 Uiso 1 1 calc GR . . . .
C13 C -0.4296(10) 0.7943(12) -0.1583(7) 0.082(3) Uani 0.478(14) 1 d D U P A 1
H13A H -0.396588 0.865756 -0.169615 0.123 Uiso 0.478(14) 1 calc GR . P A 1
H13B H -0.505048 0.808741 -0.160880 0.123 Uiso 0.478(14) 1 calc GR . P A 1
H13C H -0.428539 0.737534 -0.203331 0.123 Uiso 0.478(14) 1 calc GR . P A 1
C14 C -0.4143(10) 0.6072(11) -0.0248(10) 0.094(3) Uani 0.478(14) 1 d D U P A 1
H14A H -0.406871 0.547544 -0.065759 0.141 Uiso 0.478(14) 1 calc GR . P A 1
H14B H -0.491722 0.621887 -0.034487 0.141 Uiso 0.478(14) 1 calc GR . P A 1
H14C H -0.379246 0.581744 0.036317 0.141 Uiso 0.478(14) 1 calc GR . P A 1
C15 C -0.3507(11) 0.8531(13) 0.0458(8) 0.091(3) Uani 0.478(14) 1 d D U P A 1
H15A H -0.301579 0.828869 0.103677 0.136 Uiso 0.478(14) 1 calc GR . P A 1
H15B H -0.424918 0.860670 0.048576 0.136 Uiso 0.478(14) 1 calc GR . P A 1
H15C H -0.326437 0.927081 0.029864 0.136 Uiso 0.478(14) 1 calc GR . P A 1
C13A C -0.4201(10) 0.8388(11) -0.1378(7) 0.087(3) Uani 0.522(14) 1 d D U P A 2
H13D H -0.381099 0.911953 -0.129083 0.130 Uiso 0.522(14) 1 calc GR . P A 2
H13E H -0.495174 0.851526 -0.138487 0.130 Uiso 0.522(14) 1 calc GR . P A 2
H13F H -0.420885 0.805136 -0.194354 0.130 Uiso 0.522(14) 1 calc GR . P A 2
C14A C -0.4023(9) 0.5800(8) -0.0620(9) 0.085(3) Uani 0.522(14) 1 d D U P A 2
H14D H -0.397820 0.551204 -0.118446 0.127 Uiso 0.522(14) 1 calc GR . P A 2
H14E H -0.478315 0.577740 -0.062820 0.127 Uiso 0.522(14) 1 calc GR . P A 2
H14F H -0.357515 0.532106 -0.013479 0.127 Uiso 0.522(14) 1 calc GR . P A 2
C15A C -0.3597(10) 0.7906(14) 0.0623(7) 0.096(3) Uani 0.522(14) 1 d D U P A 2
H15D H -0.299051 0.760040 0.111211 0.144 Uiso 0.522(14) 1 calc GR . P A 2
H15E H -0.428929 0.765145 0.068641 0.144 Uiso 0.522(14) 1 calc GR . P A 2
H15F H -0.356766 0.874425 0.063316 0.144 Uiso 0.522(14) 1 calc GR . 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 1.592(3) . ?
P1 O2 1.462(3) . ?
P1 C6 1.800(3) . ?
P1 C7 1.789(3) . ?
Si1 C3 1.854(4) . ?
Si1 C13 1.859(9) . ?
Si1 C14 1.782(10) . ?
Si1 C15 1.934(10) . ?
Si1 C13A 1.851(9) . ?
Si1 C14A 1.918(9) . ?
Si1 C15A 1.816(9) . ?
O1 C1 1.452(4) . ?
C5 C6 1.338(5) . ?
C5 C2 1.428(5) . ?
C5 C4 1.531(4) . ?
C6 C16 1.477(5) . ?
C7 C12 1.389(5) . ?
C7 C8 1.384(5) . ?
C2 C1 1.5378(10) . ?
C2 C3 1.334(4) . ?
C16 C17 1.390(5) . ?
C16 C21 1.388(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.376(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.546(5) . ?
C21 H21 0.9300 . ?
C21 C20 1.381(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C8 H8 0.9300 . ?
C8 C9 1.385(5) . ?
C19 C18 1.375(6) . ?
C19 C20 1.363(6) . ?
C19 C22 1.511(6) . ?
C18 H18 0.9300 . ?
C20 H20 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.347(6) . ?
C10 H10 0.9300 . ?
C10 C9 1.378(6) . ?
C9 H9 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 0.9600 . ?
C14A H14D 0.9600 . ?
C14A H14E 0.9600 . ?
C14A H14F 0.9600 . ?
C15A H15D 0.9600 . ?
C15A H15E 0.9600 . ?
C15A H15F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C6 104.64(14) . . ?
O1 P1 C7 99.82(15) . . ?
O2 P1 O1 115.95(16) . . ?
O2 P1 C6 113.46(16) . . ?
O2 P1 C7 112.85(16) . . ?
C7 P1 C6 108.97(15) . . ?
C3 Si1 C13 109.8(4) . . ?
C3 Si1 C15 105.9(4) . . ?
C3 Si1 C14A 101.9(4) . . ?
C13 Si1 C15 109.2(5) . . ?
C14 Si1 C3 114.1(5) . . ?
C14 Si1 C13 108.3(6) . . ?
C14 Si1 C15 109.5(5) . . ?
C13A Si1 C3 110.6(4) . . ?
C13A Si1 C14A 114.5(5) . . ?
C15A Si1 C3 110.2(4) . . ?
C15A Si1 C13A 110.8(5) . . ?
C15A Si1 C14A 108.5(5) . . ?
C1 O1 P1 123.3(2) . . ?
C6 C5 C2 130.2(3) . . ?
C6 C5 C4 141.6(3) . . ?
C2 C5 C4 87.9(3) . . ?
C5 C6 P1 113.0(3) . . ?
C5 C6 C16 125.1(3) . . ?
C16 C6 P1 121.7(2) . . ?
C12 C7 P1 119.4(3) . . ?
C8 C7 P1 121.4(3) . . ?
C8 C7 C12 119.2(3) . . ?
C5 C2 C1 123.1(3) . . ?
C3 C2 C5 96.8(3) . . ?
C3 C2 C1 139.8(3) . . ?
C17 C16 C6 120.8(3) . . ?
C21 C16 C6 121.6(3) . . ?
C21 C16 C17 117.6(3) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 C7 119.6(4) . . ?
C11 C12 H12 120.2 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(4) . . ?
C18 C17 H17 119.8 . . ?
C5 C4 H4A 114.6 . . ?
C5 C4 H4B 114.6 . . ?
C5 C4 C3 84.4(3) . . ?
H4A C4 H4B 111.7 . . ?
C3 C4 H4A 114.6 . . ?
C3 C4 H4B 114.6 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.5(4) . . ?
C20 C21 H21 119.7 . . ?
O1 C1 C2 106.7(3) . . ?
O1 C1 H1A 110.4 . . ?
O1 C1 H1B 110.4 . . ?
C2 C1 H1A 110.4 . . ?
C2 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
C2 C3 Si1 137.7(3) . . ?
C2 C3 C4 90.8(3) . . ?
C4 C3 Si1 131.5(3) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C18 C19 C22 120.8(4) . . ?
C20 C19 C18 117.5(4) . . ?
C20 C19 C22 121.7(4) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 C17 121.8(4) . . ?
C19 C18 H18 119.1 . . ?
C21 C20 H20 118.9 . . ?
C19 C20 C21 122.2(4) . . ?
C19 C20 H20 118.9 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 120.9(4) . . ?
C10 C11 H11 119.5 . . ?
C11 C10 H10 119.6 . . ?
C11 C10 C9 120.7(4) . . ?
C9 C10 H10 119.6 . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 H9 120.4 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si1 C13A H13D 109.5 . . ?
Si1 C13A H13E 109.5 . . ?
Si1 C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
Si1 C14A H14D 109.5 . . ?
Si1 C14A H14E 109.5 . . ?
Si1 C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
Si1 C15A H15D 109.5 . . ?
Si1 C15A H15E 109.5 . . ?
Si1 C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O1 C1 C2 50.2(4) . . . . ?
P1 C6 C16 C17 154.2(3) . . . . ?
P1 C6 C16 C21 -27.9(4) . . . . ?
P1 C7 C12 C11 178.8(3) . . . . ?
P1 C7 C8 C9 -178.8(3) . . . . ?
O1 P1 C6 C5 19.7(3) . . . . ?
O1 P1 C6 C16 -165.1(2) . . . . ?
O1 P1 C7 C12 -131.4(3) . . . . ?
O1 P1 C7 C8 47.8(3) . . . . ?
O2 P1 O1 C1 75.9(3) . . . . ?
O2 P1 C6 C5 -107.7(3) . . . . ?
O2 P1 C6 C16 67.6(3) . . . . ?
O2 P1 C7 C12 -7.7(4) . . . . ?
O2 P1 C7 C8 171.5(3) . . . . ?
C5 C6 C16 C17 -31.1(5) . . . . ?
C5 C6 C16 C21 146.8(3) . . . . ?
C5 C2 C1 O1 -21.1(5) . . . . ?
C5 C2 C3 Si1 -178.7(3) . . . . ?
C5 C2 C3 C4 1.4(3) . . . . ?
C5 C4 C3 Si1 178.8(3) . . . . ?
C5 C4 C3 C2 -1.3(3) . . . . ?
C6 P1 O1 C1 -49.9(3) . . . . ?
C6 P1 C7 C12 119.3(3) . . . . ?
C6 P1 C7 C8 -61.5(3) . . . . ?
C6 C5 C2 C1 -2.6(6) . . . . ?
C6 C5 C2 C3 173.2(4) . . . . ?
C6 C5 C4 C3 -172.1(5) . . . . ?
C6 C16 C17 C18 177.1(3) . . . . ?
C6 C16 C21 C20 -176.6(3) . . . . ?
C7 P1 O1 C1 -162.6(3) . . . . ?
C7 P1 C6 C5 125.7(3) . . . . ?
C7 P1 C6 C16 -59.0(3) . . . . ?
C7 C12 C11 C10 0.2(6) . . . . ?
C7 C8 C9 C10 -0.2(6) . . . . ?
C2 C5 C6 P1 2.0(5) . . . . ?
C2 C5 C6 C16 -173.1(3) . . . . ?
C2 C5 C4 C3 1.3(3) . . . . ?
C16 C17 C18 C19 0.1(6) . . . . ?
C16 C21 C20 C19 -1.3(6) . . . . ?
C12 C7 C8 C9 0.5(6) . . . . ?
C12 C11 C10 C9 0.1(6) . . . . ?
C17 C16 C21 C20 1.4(5) . . . . ?
C4 C5 C6 P1 173.3(4) . . . . ?
C4 C5 C6 C16 -1.8(7) . . . . ?
C4 C5 C2 C1 -177.2(3) . . . . ?
C4 C5 C2 C3 -1.5(3) . . . . ?
C21 C16 C17 C18 -0.8(5) . . . . ?
C1 C2 C3 Si1 -4.2(8) . . . . ?
C1 C2 C3 C4 175.9(5) . . . . ?
C3 C2 C1 O1 165.4(4) . . . . ?
C8 C7 C12 C11 -0.5(5) . . . . ?
C18 C19 C20 C21 0.5(6) . . . . ?
C20 C19 C18 C17 0.0(6) . . . . ?
C11 C10 C9 C8 -0.1(6) . . . . ?
C22 C19 C18 C17 178.7(4) . . . . ?
C22 C19 C20 C21 -178.1(4) . . . . ?
C13 Si1 C3 C2 117.7(6) . . . . ?
C13 Si1 C3 C4 -62.5(6) . . . . ?
C14 Si1 C3 C2 -120.6(7) . . . . ?
C14 Si1 C3 C4 59.2(7) . . . . ?
C15 Si1 C3 C2 -0.1(7) . . . . ?
C15 Si1 C3 C4 179.6(6) . . . . ?
C13A Si1 C3 C2 98.1(6) . . . . ?
C13A Si1 C3 C4 -82.1(6) . . . . ?
C14A Si1 C3 C2 -139.8(6) . . . . ?
C14A Si1 C3 C4 40.0(5) . . . . ?
C15A Si1 C3 C2 -24.8(7) . . . . ?
C15A Si1 C3 C4 155.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
