# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 2162638'
loop_
_audit_author_name
_audit_author_address
'Ailong Shao'
;Fuyang Normal University
China
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 O2 P'
_chemical_formula_sum            'C20 H15 O2 P'
_chemical_formula_weight         318.29

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_space_group_name_Hall           '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4992(2)
_cell_length_b                   10.3406(3)
_cell_length_c                   18.4801(5)
_cell_angle_alpha                106.090(3)
_cell_angle_beta                 95.138(2)
_cell_angle_gamma                107.576(2)
_cell_volume                     1632.71(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11588
_cell_measurement_theta_min      2.1170
_cell_measurement_theta_max      29.5990


_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9510
_exptl_absorpt_correction_T_max  0.9559
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19106
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6417
_reflns_number_gt                5365
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0757P)²+0.1558P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6417
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.68277(19) 0.19999(17) 0.57217(9) 0.0481(4) Uani 1 1 d . . .
C2 C 0.5660(2) 0.2393(2) 0.54549(10) 0.0583(4) Uani 1 1 d . . .
H2 H 0.4657 0.1818 0.5368 0.070 Uiso 1 1 calc R . .
C3 C 0.6088(3) 0.3691(2) 0.53282(11) 0.0674(5) Uani 1 1 d . . .
H3 H 0.5349 0.4003 0.5146 0.081 Uiso 1 1 calc R . .
C4 C 0.7580(3) 0.4554(2) 0.54617(11) 0.0698(5) Uani 1 1 d . . .
H4 H 0.7814 0.5435 0.5378 0.084 Uiso 1 1 calc R . .
C5 C 0.8720(2) 0.41370(19) 0.57154(11) 0.0620(5) Uani 1 1 d . . .
H5 H 0.9721 0.4715 0.5797 0.074 Uiso 1 1 calc R . .
C6 C 0.83322(19) 0.28124(17) 0.58483(9) 0.0490(4) Uani 1 1 d . . .
C7 C 0.91381(19) 0.19984(18) 0.60956(9) 0.0510(4) Uani 1 1 d . . .
H7 H 1.0177 0.2262 0.6227 0.061 Uiso 1 1 calc R . .
C8 C 0.81144(18) 0.07815(17) 0.61024(9) 0.0473(4) Uani 1 1 d . . .
C9 C 0.74963(17) -0.08521(18) 0.71266(10) 0.0511(4) Uani 1 1 d . . .
C10 C 0.7443(2) 0.0351(2) 0.76633(12) 0.0687(5) Uani 1 1 d . . .
H10 H 0.7780 0.1234 0.7584 0.082 Uiso 1 1 calc R . .
C11 C 0.6893(3) 0.0248(3) 0.83182(14) 0.0858(7) Uani 1 1 d . . .
H11 H 0.6856 0.1063 0.8678 0.103 Uiso 1 1 calc R . .
C12 C 0.6401(2) -0.1046(3) 0.84411(15) 0.0840(7) Uani 1 1 d . . .
H12 H 0.6025 -0.1110 0.8882 0.101 Uiso 1 1 calc R . .
C13 C 0.6462(3) -0.2238(3) 0.79185(15) 0.0854(7) Uani 1 1 d . . .
H13 H 0.6140 -0.3113 0.8007 0.103 Uiso 1 1 calc R . .
C14 C 0.6997(2) -0.2156(2) 0.72581(13) 0.0710(5) Uani 1 1 d . . .
H14 H 0.7023 -0.2978 0.6900 0.085 Uiso 1 1 calc R . .
C15 C 1.02615(18) -0.03643(17) 0.65454(9) 0.0464(4) Uani 1 1 d . . .
C16 C 1.1042(2) -0.0812(3) 0.59885(12) 0.0770(6) Uani 1 1 d . . .
H16 H 1.0534 -0.1316 0.5486 0.092 Uiso 1 1 calc R . .
C17 C 1.2561(3) -0.0519(3) 0.61707(14) 0.0916(8) Uani 1 1 d . . .
H17 H 1.3074 -0.0814 0.5788 0.110 Uiso 1 1 calc R . .
C18 C 1.3326(2) 0.0193(2) 0.68994(13) 0.0684(5) Uani 1 1 d . . .
H18 H 1.4355 0.0379 0.7016 0.082 Uiso 1 1 calc R . .
C19 C 1.2575(2) 0.0636(2) 0.74603(12) 0.0658(5) Uani 1 1 d . . .
H19 H 1.3092 0.1124 0.7962 0.079 Uiso 1 1 calc R . .
C20 C 1.10536(19) 0.0360(2) 0.72848(10) 0.0566(4) Uani 1 1 d . . .
H20 H 1.0551 0.0666 0.7671 0.068 Uiso 1 1 calc R . .
C21 C 0.29917(18) 1.03241(16) 0.93842(9) 0.0448(4) Uani 1 1 d . . .
C22 C 0.4176(2) 1.16137(18) 0.96646(10) 0.0576(4) Uani 1 1 d . . .
H22 H 0.5169 1.1660 0.9772 0.069 Uiso 1 1 calc R . .
C23 C 0.3786(3) 1.2815(2) 0.97720(12) 0.0697(5) Uani 1 1 d . . .
H23 H 0.4537 1.3710 0.9965 0.084 Uiso 1 1 calc R . .
C24 C 0.2303(3) 1.2738(2) 0.96021(13) 0.0758(6) Uani 1 1 d . . .
H24 H 0.2091 1.3579 0.9664 0.091 Uiso 1 1 calc R . .
C25 C 0.1140(2) 1.1446(2) 0.93441(12) 0.0661(5) Uani 1 1 d . . .
H25 H 0.0146 1.1404 0.9248 0.079 Uiso 1 1 calc R . .
C26 C 0.14999(19) 1.02006(17) 0.92309(9) 0.0483(4) Uani 1 1 d . . .
C27 C 0.06759(18) 0.86894(18) 0.89556(10) 0.0494(4) Uani 1 1 d . . .
H27 H -0.0362 0.8257 0.8805 0.059 Uiso 1 1 calc R . .
C28 C 0.16815(17) 0.80220(16) 0.89565(9) 0.0455(4) Uani 1 1 d . . .
C29 C 0.2391(2) 0.6566(2) 0.73620(11) 0.0609(5) Uani 1 1 d . . .
H29 H 0.2153 0.7400 0.7488 0.073 Uiso 1 1 calc R . .
C30 C 0.2864(2) 0.6123(3) 0.66813(13) 0.0763(6) Uani 1 1 d . . .
H30 H 0.2949 0.6663 0.6350 0.092 Uiso 1 1 calc R . .
C31 C 0.3212(2) 0.4887(3) 0.64895(13) 0.0773(6) Uani 1 1 d . . .
H31 H 0.3512 0.4585 0.6025 0.093 Uiso 1 1 calc R . .
C32 C 0.3118(2) 0.4105(2) 0.69767(13) 0.0689(5) Uani 1 1 d . . .
H32 H 0.3366 0.3277 0.6847 0.083 Uiso 1 1 calc R . .
C33 C 0.2655(2) 0.45365(19) 0.76627(11) 0.0577(4) Uani 1 1 d . . .
H33 H 0.2600 0.4001 0.7996 0.069 Uiso 1 1 calc R . .
C34 C 0.22713(17) 0.57656(17) 0.78584(10) 0.0480(4) Uani 1 1 d . . .
C35 C -0.04663(17) 0.52517(15) 0.84535(9) 0.0446(3) Uani 1 1 d . . .
C36 C -0.12893(19) 0.5077(2) 0.77555(10) 0.0591(5) Uani 1 1 d . . .
H36 H -0.0805 0.5426 0.7398 0.071 Uiso 1 1 calc R . .
C37 C -0.2822(2) 0.4389(2) 0.75877(12) 0.0684(5) Uani 1 1 d . . .
H37 H -0.3370 0.4270 0.7117 0.082 Uiso 1 1 calc R . .
C38 C -0.3543(2) 0.3878(2) 0.81163(12) 0.0653(5) Uani 1 1 d . . .
H38 H -0.4580 0.3423 0.8004 0.078 Uiso 1 1 calc R . .
C39 C -0.2745(2) 0.4034(2) 0.88052(12) 0.0705(5) Uani 1 1 d . . .
H39 H -0.3236 0.3684 0.9161 0.085 Uiso 1 1 calc R . .
C40 C -0.1206(2) 0.4715(2) 0.89730(11) 0.0618(5) Uani 1 1 d . . .
H40 H -0.0663 0.4813 0.9441 0.074 Uiso 1 1 calc R . .
O1 O 0.75600(15) -0.21051(13) 0.56131(8) 0.0646(3) Uani 1 1 d . . .
O2 O 0.66607(12) 0.07443(11) 0.58783(7) 0.0510(3) Uani 1 1 d . . .
O3 O 0.22533(14) 0.58590(13) 0.93626(7) 0.0600(3) Uani 1 1 d . . .
O4 O 0.31370(11) 0.89997(11) 0.92209(7) 0.0484(3) Uani 1 1 d . . .
P1 P 0.15326(4) 0.61801(4) 0.87245(2) 0.04471(13) Uani 1 1 d . . .
P2 P 0.82655(5) -0.07967(4) 0.62769(2) 0.04709(13) Uani 1 1 d . . .


_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
C1 O2 1.374(2) . ?
C1 C6 1.382(2) . ?
C1 C2 1.388(2) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.429(2) . ?
C7 C8 1.342(2) . ?
C7 H7 0.9300 . ?
C8 O2 1.3916(18) . ?
C8 P2 1.7924(17) . ?
C9 C10 1.377(3) . ?
C9 C14 1.385(3) . ?
C9 P2 1.7980(18) . ?
C10 C11 1.379(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.379(2) . ?
C15 C16 1.379(2) . ?
C15 P2 1.7994(16) . ?
C16 C17 1.371(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.355(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O4 1.3704(19) . ?
C21 C26 1.380(2) . ?
C21 C22 1.385(2) . ?
C22 C23 1.369(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.376(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.396(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.436(2) . ?
C27 C28 1.337(2) . ?
C27 H27 0.9300 . ?
C28 O4 1.3905(18) . ?
C28 P1 1.7903(16) . ?
C29 C30 1.379(3) . ?
C29 C34 1.387(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.376(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.359(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.380(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.388(2) . ?
C33 H33 0.9300 . ?
C34 P1 1.8000(17) . ?
C35 C40 1.380(2) . ?
C35 C36 1.383(2) . ?
C35 P1 1.8000(16) . ?
C36 C37 1.376(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.375(3) . ?
C37 H37 0.9300 . ?
C38 C39 1.364(3) . ?
C38 H38 0.9300 . ?
C39 C40 1.380(3) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
O1 P2 1.4731(12) . ?
O3 P1 1.4763(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 C6 110.54(14) . . ?
O2 C1 C2 125.20(16) . . ?
C6 C1 C2 124.24(17) . . ?
C3 C2 C1 115.30(18) . . ?
C3 C2 H2 122.3 . . ?
C1 C2 H2 122.3 . . ?
C2 C3 C4 122.46(19) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 121.33(19) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.08(18) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 118.56(16) . . ?
C1 C6 C7 105.77(14) . . ?
C5 C6 C7 135.67(17) . . ?
C8 C7 C6 107.14(15) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C7 C8 O2 111.06(14) . . ?
C7 C8 P2 132.96(13) . . ?
O2 C8 P2 115.82(11) . . ?
C10 C9 C14 118.99(19) . . ?
C10 C9 P2 122.85(14) . . ?
C14 C9 P2 118.10(15) . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 120.1(2) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C20 C15 C16 117.90(16) . . ?
C20 C15 P2 123.54(13) . . ?
C16 C15 P2 118.54(13) . . ?
C17 C16 C15 120.40(18) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 121.14(18) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 119.43(19) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C20 120.07(18) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 121.06(17) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
O4 C21 C26 110.72(13) . . ?
O4 C21 C22 124.87(15) . . ?
C26 C21 C22 124.41(16) . . ?
C23 C22 C21 115.45(18) . . ?
C23 C22 H22 122.3 . . ?
C21 C22 H22 122.3 . . ?
C22 C23 C24 121.99(18) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C25 C24 C23 121.56(19) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C24 C25 C26 117.81(19) . . ?
C24 C25 H25 121.1 . . ?
C26 C25 H25 121.1 . . ?
C21 C26 C25 118.71(16) . . ?
C21 C26 C27 105.48(14) . . ?
C25 C26 C27 135.78(17) . . ?
C28 C27 C26 107.10(14) . . ?
C28 C27 H27 126.4 . . ?
C26 C27 H27 126.4 . . ?
C27 C28 O4 111.16(13) . . ?
C27 C28 P1 133.72(12) . . ?
O4 C28 P1 115.08(11) . . ?
C30 C29 C34 119.83(19) . . ?
C30 C29 H29 120.1 . . ?
C34 C29 H29 120.1 . . ?
C31 C30 C29 120.4(2) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C30 120.2(2) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C33 120.21(19) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C34 120.35(19) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C29 C34 C33 118.98(17) . . ?
C29 C34 P1 123.14(13) . . ?
C33 C34 P1 117.77(14) . . ?
C40 C35 C36 118.90(16) . . ?
C40 C35 P1 118.22(13) . . ?
C36 C35 P1 122.87(13) . . ?
C37 C36 C35 120.30(17) . . ?
C37 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C36 C37 C38 120.00(18) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C39 C38 C37 120.36(17) . . ?
C39 C38 H38 119.8 . . ?
C37 C38 H38 119.8 . . ?
C38 C39 C40 119.76(18) . . ?
C38 C39 H39 120.1 . . ?
C40 C39 H39 120.1 . . ?
C39 C40 C35 120.67(18) . . ?
C39 C40 H40 119.7 . . ?
C35 C40 H40 119.7 . . ?
C1 O2 C8 105.48(12) . . ?
C21 O4 C28 105.54(12) . . ?
O3 P1 C28 113.02(7) . . ?
O3 P1 C35 113.62(8) . . ?
C28 P1 C35 102.93(7) . . ?
O3 P1 C34 114.19(8) . . ?
C28 P1 C34 106.21(8) . . ?
C35 P1 C34 105.90(7) . . ?
O1 P2 C8 113.33(8) . . ?
O1 P2 C9 114.21(8) . . ?
C8 P2 C9 105.36(8) . . ?
O1 P2 C15 113.17(8) . . ?
C8 P2 C15 103.28(7) . . ?
C9 P2 C15 106.55(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
O2 C1 C2 C3 -179.23(16) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
O2 C1 C6 C5 179.84(15) . . . . ?
C2 C1 C6 C5 1.3(2) . . . . ?
O2 C1 C6 C7 0.23(18) . . . . ?
C2 C1 C6 C7 -178.28(16) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 179.11(19) . . . . ?
C1 C6 C7 C8 0.18(18) . . . . ?
C5 C6 C7 C8 -179.3(2) . . . . ?
C6 C7 C8 O2 -0.52(19) . . . . ?
C6 C7 C8 P2 174.69(14) . . . . ?
C14 C9 C10 C11 -0.3(3) . . . . ?
P2 C9 C10 C11 -177.49(17) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C9 0.9(4) . . . . ?
C10 C9 C14 C13 -0.2(3) . . . . ?
P2 C9 C14 C13 177.08(17) . . . . ?
C20 C15 C16 C17 -1.0(4) . . . . ?
P2 C15 C16 C17 -179.3(2) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C18 C19 C20 C15 0.1(3) . . . . ?
C16 C15 C20 C19 0.4(3) . . . . ?
P2 C15 C20 C19 178.62(15) . . . . ?
O4 C21 C22 C23 178.55(16) . . . . ?
C26 C21 C22 C23 -1.4(3) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C25 2.6(3) . . . . ?
C23 C24 C25 C26 -2.2(3) . . . . ?
O4 C21 C26 C25 -178.29(16) . . . . ?
C22 C21 C26 C25 1.7(3) . . . . ?
O4 C21 C26 C27 0.13(18) . . . . ?
C22 C21 C26 C27 -179.88(17) . . . . ?
C24 C25 C26 C21 0.2(3) . . . . ?
C24 C25 C26 C27 -177.6(2) . . . . ?
C21 C26 C27 C28 -0.27(19) . . . . ?
C25 C26 C27 C28 177.7(2) . . . . ?
C26 C27 C28 O4 0.31(19) . . . . ?
C26 C27 C28 P1 177.80(14) . . . . ?
C34 C29 C30 C31 0.3(3) . . . . ?
C29 C30 C31 C32 -1.2(3) . . . . ?
C30 C31 C32 C33 0.8(3) . . . . ?
C31 C32 C33 C34 0.5(3) . . . . ?
C30 C29 C34 C33 1.0(3) . . . . ?
C30 C29 C34 P1 -175.22(15) . . . . ?
C32 C33 C34 C29 -1.4(3) . . . . ?
C32 C33 C34 P1 175.02(14) . . . . ?
C40 C35 C36 C37 0.6(3) . . . . ?
P1 C35 C36 C37 -178.31(15) . . . . ?
C35 C36 C37 C38 0.3(3) . . . . ?
C36 C37 C38 C39 -0.7(3) . . . . ?
C37 C38 C39 C40 0.3(3) . . . . ?
C38 C39 C40 C35 0.6(3) . . . . ?
C36 C35 C40 C39 -1.0(3) . . . . ?
P1 C35 C40 C39 177.91(16) . . . . ?
C6 C1 O2 C8 -0.53(17) . . . . ?
C2 C1 O2 C8 177.96(15) . . . . ?
C7 C8 O2 C1 0.65(18) . . . . ?
P2 C8 O2 C1 -175.45(11) . . . . ?
C26 C21 O4 C28 0.04(17) . . . . ?
C22 C21 O4 C28 -179.94(16) . . . . ?
C27 C28 O4 C21 -0.22(18) . . . . ?
P1 C28 O4 C21 -178.22(11) . . . . ?
C27 C28 P1 O3 -122.99(18) . . . . ?
O4 C28 P1 O3 54.43(14) . . . . ?
C27 C28 P1 C35 -0.01(19) . . . . ?
O4 C28 P1 C35 177.40(11) . . . . ?
C27 C28 P1 C34 111.06(18) . . . . ?
O4 C28 P1 C34 -71.53(13) . . . . ?
C40 C35 P1 O3 19.46(17) . . . . ?
C36 C35 P1 O3 -161.67(14) . . . . ?
C40 C35 P1 C28 -103.12(15) . . . . ?
C36 C35 P1 C28 75.75(16) . . . . ?
C40 C35 P1 C34 145.58(14) . . . . ?
C36 C35 P1 C34 -35.55(17) . . . . ?
C29 C34 P1 O3 -145.65(14) . . . . ?
C33 C34 P1 O3 38.13(16) . . . . ?
C29 C34 P1 C28 -20.40(17) . . . . ?
C33 C34 P1 C28 163.37(13) . . . . ?
C29 C34 P1 C35 88.57(16) . . . . ?
C33 C34 P1 C35 -87.65(14) . . . . ?
C7 C8 P2 O1 -118.01(17) . . . . ?
O2 C8 P2 O1 57.02(14) . . . . ?
C7 C8 P2 C9 116.42(18) . . . . ?
O2 C8 P2 C9 -68.54(13) . . . . ?
C7 C8 P2 C15 4.81(19) . . . . ?
O2 C8 P2 C15 179.84(11) . . . . ?
C10 C9 P2 O1 -149.19(15) . . . . ?
C14 C9 P2 O1 33.62(17) . . . . ?
C10 C9 P2 C8 -24.17(17) . . . . ?
C14 C9 P2 C8 158.65(15) . . . . ?
C10 C9 P2 C15 85.11(17) . . . . ?
C14 C9 P2 C15 -92.08(16) . . . . ?
C20 C15 P2 O1 -150.98(15) . . . . ?
C16 C15 P2 O1 27.18(19) . . . . ?
C20 C15 P2 C8 86.09(17) . . . . ?
C16 C15 P2 C8 -95.75(18) . . . . ?
C20 C15 P2 C9 -24.65(18) . . . . ?
C16 C15 P2 C9 153.52(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2162640'
loop_
_audit_author_name
_audit_author_address
'Ailong Shao'
;Fuyang Normal University
China
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 N0 O P S2'
_chemical_formula_sum            'C18 H13 N0 O P S2'
_chemical_formula_weight         340.37

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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

loop_
_symmetry_equiv_pos_as_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                   8.5680(6)
_cell_length_b                   9.8972(5)
_cell_length_c                   19.3273(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1638.94(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3331
_cell_measurement_theta_min      2.306
_cell_measurement_theta_max      28.09

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8773
_exptl_absorpt_correction_T_max  0.8986
_exptl_absorpt_process_details   'SADABS; Bruker,2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4801
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2715
_reflns_number_gt                2408
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0525P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_number_reflns         2715
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0528(3) 0.3052(2) 0.14390(14) 0.0454(6) Uani 1 1 d . . .
C2 C 1.1362(4) 0.3170(3) 0.20539(16) 0.0583(7) Uani 1 1 d . . .
H2 H 1.0848 0.3383 0.2463 0.070 Uiso 1 1 calc R . .
C3 C 1.2953(4) 0.2969(3) 0.2053(2) 0.0693(9) Uani 1 1 d . . .
H3 H 1.3509 0.3060 0.2463 0.083 Uiso 1 1 calc R . .
C4 C 1.3729(4) 0.2636(3) 0.14577(19) 0.0703(9) Uani 1 1 d . . .
H4 H 1.4801 0.2492 0.1466 0.084 Uiso 1 1 calc R . .
C5 C 1.2919(4) 0.2517(3) 0.08492(18) 0.0714(9) Uani 1 1 d . . .
H5 H 1.3445 0.2301 0.0443 0.086 Uiso 1 1 calc R . .
C6 C 1.1329(4) 0.2716(3) 0.08388(15) 0.0608(8) Uani 1 1 d . . .
H6 H 1.0785 0.2623 0.0425 0.073 Uiso 1 1 calc R . .
C7 C 0.7698(3) 0.3125(3) 0.22409(14) 0.0471(6) Uani 1 1 d . . .
C8 C 0.7297(4) 0.1833(3) 0.24586(15) 0.0606(8) Uani 1 1 d . . .
H8 H 0.7407 0.1105 0.2158 0.073 Uiso 1 1 calc R . .
C9 C 0.6735(5) 0.1625(3) 0.31203(17) 0.0748(9) Uani 1 1 d . . .
H9 H 0.6488 0.0753 0.3263 0.090 Uiso 1 1 calc R . .
C10 C 0.6538(5) 0.2672(4) 0.35657(16) 0.0771(10) Uani 1 1 d . . .
H10 H 0.6166 0.2519 0.4011 0.093 Uiso 1 1 calc R . .
C11 C 0.6890(6) 0.3946(4) 0.33542(18) 0.0994(15) Uani 1 1 d . . .
H11 H 0.6740 0.4667 0.3655 0.119 Uiso 1 1 calc R . .
C12 C 0.7472(5) 0.4185(3) 0.26947(17) 0.0825(12) Uani 1 1 d . . .
H12 H 0.7710 0.5062 0.2558 0.099 Uiso 1 1 calc R . .
C13 C 0.8220(3) 0.5055(2) 0.11309(13) 0.0454(6) Uani 1 1 d . . .
C14 C 0.9039(4) 0.6166(3) 0.13253(14) 0.0554(7) Uani 1 1 d . . .
H14 H 0.9883 0.6152 0.1628 0.066 Uiso 1 1 calc R . .
C15 C 0.8443(4) 0.7353(2) 0.10062(13) 0.0476(6) Uani 1 1 d . . .
C16 C 0.7225(4) 0.7110(2) 0.05656(15) 0.0512(7) Uani 1 1 d . . .
C17 C 0.6637(5) 0.8298(3) 0.02337(16) 0.0700(9) Uani 1 1 d . . .
H17 H 0.5816 0.8310 -0.0081 0.084 Uiso 1 1 calc R . .
C18 C 0.7436(4) 0.9394(3) 0.04397(16) 0.0684(9) Uani 1 1 d . . .
H18 H 0.7214 1.0261 0.0283 0.082 Uiso 1 1 calc R . .
O1 O 0.7685(2) 0.24178(19) 0.08732(10) 0.0559(5) Uani 1 1 d . . .
P1 P 0.84558(8) 0.33168(6) 0.13781(3) 0.04421(18) Uani 1 1 d . . .
S1 S 0.67599(10) 0.54166(7) 0.05408(4) 0.0640(2) Uani 1 1 d . . .
S2 S 0.89012(12) 0.90530(7) 0.10162(4) 0.0740(3) Uani 1 1 d . . .


_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
C1 C6 1.388(4) . ?
C1 C2 1.392(4) . ?
C1 P1 1.799(3) . ?
C2 C3 1.377(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.381(4) . ?
C7 C8 1.389(4) . ?
C7 P1 1.800(3) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.358(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.360(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.358(4) . ?
C13 S1 1.730(3) . ?
C13 P1 1.797(2) . ?
C14 C15 1.422(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(4) . ?
C15 S2 1.728(2) . ?
C16 C17 1.431(4) . ?
C16 S1 1.723(3) . ?
C17 C18 1.343(4) . ?
C17 H17 0.9300 . ?
C18 S2 1.712(4) . ?
C18 H18 0.9300 . ?
O1 P1 1.4763(19) . ?

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
C6 C1 C2 118.7(3) . . ?
C6 C1 P1 117.9(2) . . ?
C2 C1 P1 123.4(2) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C12 C7 C8 118.2(3) . . ?
C12 C7 P1 124.0(2) . . ?
C8 C7 P1 117.8(2) . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C7 C12 C11 120.2(3) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 S1 112.87(19) . . ?
C14 C13 P1 130.1(2) . . ?
S1 C13 P1 117.04(14) . . ?
C13 C14 C15 111.3(3) . . ?
C13 C14 H14 124.3 . . ?
C15 C14 H14 124.3 . . ?
C16 C15 C14 113.5(2) . . ?
C16 C15 S2 110.59(19) . . ?
C14 C15 S2 135.9(2) . . ?
C15 C16 C17 113.8(2) . . ?
C15 C16 S1 111.39(19) . . ?
C17 C16 S1 134.8(2) . . ?
C18 C17 C16 110.5(3) . . ?
C18 C17 H17 124.7 . . ?
C16 C17 H17 124.7 . . ?
C17 C18 S2 114.1(2) . . ?
C17 C18 H18 123.0 . . ?
S2 C18 H18 123.0 . . ?
O1 P1 C13 110.55(12) . . ?
O1 P1 C7 112.81(12) . . ?
C13 P1 C7 107.87(12) . . ?
O1 P1 C1 113.38(12) . . ?
C13 P1 C1 105.52(12) . . ?
C7 P1 C1 106.28(13) . . ?
C16 S1 C13 90.89(13) . . ?
C18 S2 C15 91.02(14) . . ?

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
C6 C1 C2 C3 0.8(4) . . . . ?
P1 C1 C2 C3 -179.1(2) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C5 C6 C1 0.7(5) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
P1 C1 C6 C5 179.2(2) . . . . ?
C12 C7 C8 C9 -2.0(5) . . . . ?
P1 C7 C8 C9 178.9(3) . . . . ?
C7 C8 C9 C10 1.1(6) . . . . ?
C8 C9 C10 C11 0.5(7) . . . . ?
C9 C10 C11 C12 -1.1(7) . . . . ?
C8 C7 C12 C11 1.4(6) . . . . ?
P1 C7 C12 C11 -179.6(3) . . . . ?
C10 C11 C12 C7 0.2(7) . . . . ?
S1 C13 C14 C15 1.9(3) . . . . ?
P1 C13 C14 C15 -179.5(2) . . . . ?
C13 C14 C15 C16 -1.8(4) . . . . ?
C13 C14 C15 S2 -179.8(2) . . . . ?
C14 C15 C16 C17 -179.0(3) . . . . ?
S2 C15 C16 C17 -0.5(3) . . . . ?
C14 C15 C16 S1 0.9(3) . . . . ?
S2 C15 C16 S1 179.40(15) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
S1 C16 C17 C18 -180.0(3) . . . . ?
C16 C17 C18 S2 0.7(4) . . . . ?
C14 C13 P1 O1 -160.7(3) . . . . ?
S1 C13 P1 O1 17.9(2) . . . . ?
C14 C13 P1 C7 75.5(3) . . . . ?
S1 C13 P1 C7 -105.90(17) . . . . ?
C14 C13 P1 C1 -37.7(3) . . . . ?
S1 C13 P1 C1 140.82(16) . . . . ?
C12 C7 P1 O1 -141.5(3) . . . . ?
C8 C7 P1 O1 37.6(3) . . . . ?
C12 C7 P1 C13 -19.1(3) . . . . ?
C8 C7 P1 C13 160.0(2) . . . . ?
C12 C7 P1 C1 93.7(3) . . . . ?
C8 C7 P1 C1 -87.3(2) . . . . ?
C6 C1 P1 O1 35.3(3) . . . . ?
C2 C1 P1 O1 -144.8(2) . . . . ?
C6 C1 P1 C13 -85.8(2) . . . . ?
C2 C1 P1 C13 94.1(2) . . . . ?
C6 C1 P1 C7 159.8(2) . . . . ?
C2 C1 P1 C7 -20.3(3) . . . . ?
C15 C16 S1 C13 0.1(2) . . . . ?
C17 C16 S1 C13 180.0(3) . . . . ?
C14 C13 S1 C16 -1.2(2) . . . . ?
P1 C13 S1 C16 179.98(17) . . . . ?
C17 C18 S2 C15 -0.8(3) . . . . ?
C16 C15 S2 C18 0.7(2) . . . . ?
C14 C15 S2 C18 178.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.282
_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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2162641'
loop_
_audit_author_name
_audit_author_address
'Ailong Shao'
;Fuyang Normal University
China
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 N O P, H2 O'
_chemical_formula_sum            'C26 H22 N O2 P'
_chemical_formula_weight         411.42

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'
N N 0.0061 0.0033 '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'


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_space_group_name_Hall           '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   9.9038(3)
_cell_length_b                   14.8253(5)
_cell_length_c                   14.9817(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.847(3)
_cell_angle_gamma                90.00
_cell_volume                     2135.79(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6576
_cell_measurement_theta_min      2.239
_cell_measurement_theta_max      28.259

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_T_max  0.9689
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13743
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3761
_reflns_number_gt                3002
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0842P)²+0.1047P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3761
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.98465(19) 0.93306(14) 0.11454(13) 0.0637(5) Uani 1 1 d . . .
H1 H 0.9665 0.9894 0.0870 0.076 Uiso 1 1 calc R . .
C2 C 1.0602(2) 0.87009(16) 0.07854(14) 0.0715(6) Uani 1 1 d . . .
H2 H 1.0920 0.8843 0.0267 0.086 Uiso 1 1 calc R . .
C3 C 1.0883(2) 0.78750(15) 0.11849(15) 0.0690(5) Uani 1 1 d . . .
H3 H 1.1390 0.7454 0.0940 0.083 Uiso 1 1 calc R . .
C4 C 1.0415(2) 0.76690(14) 0.19505(16) 0.0731(6) Uani 1 1 d . . .
H4 H 1.0609 0.7106 0.2226 0.088 Uiso 1 1 calc R . .
C5 C 0.9658(2) 0.82882(14) 0.23161(14) 0.0659(5) Uani 1 1 d . . .
H5 H 0.9347 0.8141 0.2836 0.079 Uiso 1 1 calc R . .
C6 C 0.93582(15) 0.91265(12) 0.19142(11) 0.0504(4) Uani 1 1 d . . .
C7 C 0.84516(17) 1.09893(12) 0.19163(12) 0.0538(4) Uani 1 1 d . . .
C8 C 0.9701(2) 1.14729(15) 0.21195(15) 0.0709(6) Uani 1 1 d . . .
H8 H 1.0486 1.1230 0.2514 0.085 Uiso 1 1 calc R . .
C9 C 0.9764(3) 1.23164(16) 0.17299(19) 0.0851(7) Uani 1 1 d . . .
H9 H 1.0599 1.2633 0.1858 0.102 Uiso 1 1 calc R . .
C10 C 0.8607(3) 1.26884(15) 0.11586(17) 0.0821(7) Uani 1 1 d . . .
H10 H 0.8660 1.3257 0.0907 0.099 Uiso 1 1 calc R . .
C11 C 0.7374(3) 1.22271(15) 0.09571(16) 0.0769(6) Uani 1 1 d . . .
H11 H 0.6592 1.2482 0.0569 0.092 Uiso 1 1 calc R . .
C12 C 0.72938(19) 1.13792(14) 0.13326(13) 0.0620(5) Uani 1 1 d . . .
H12 H 0.6455 1.1067 0.1192 0.074 Uiso 1 1 calc R . .
C13 C 0.6624(2) 0.90293(17) -0.00048(14) 0.0769(6) Uani 1 1 d . . .
H13 H 0.6580 0.9656 -0.0011 0.092 Uiso 1 1 calc R . .
C14 C 0.7000(3) 0.8567(2) -0.07198(16) 0.0977(9) Uani 1 1 d . . .
H14 H 0.7212 0.8889 -0.1201 0.117 Uiso 1 1 calc R . .
C15 C 0.7061(2) 0.7646(2) -0.07194(17) 0.0907(8) Uani 1 1 d . . .
H15 H 0.7320 0.7345 -0.1197 0.109 Uiso 1 1 calc R . .
C16 C 0.6742(2) 0.71643(19) -0.00175(17) 0.0898(7) Uani 1 1 d . . .
H16 H 0.6774 0.6537 -0.0020 0.108 Uiso 1 1 calc R . .
C17 C 0.6369(2) 0.76176(17) 0.06976(16) 0.0775(6) Uani 1 1 d . . .
H17 H 0.6153 0.7290 0.1174 0.093 Uiso 1 1 calc R . .
C18 C 0.63153(16) 0.85515(14) 0.07126(12) 0.0568(5) Uani 1 1 d . . .
C19 C 0.58611(16) 0.90106(13) 0.14723(12) 0.0542(4) Uani 1 1 d . . .
C20 C 0.45091(18) 0.89540(14) 0.15938(13) 0.0651(5) Uani 1 1 d . . .
H20 H 0.3781 0.8635 0.1219 0.078 Uiso 1 1 calc R . .
C21 C 0.44265(17) 0.94469(13) 0.23582(13) 0.0578(5) Uani 1 1 d . . .
C22 C 0.3373(2) 0.96155(17) 0.28288(16) 0.0724(6) Uani 1 1 d . . .
H22 H 0.2489 0.9376 0.2603 0.087 Uiso 1 1 calc R . .
C23 C 0.3634(2) 1.01177(15) 0.35997(16) 0.0750(6) Uani 1 1 d . . .
H23 H 0.2938 1.0219 0.3909 0.090 Uiso 1 1 calc R . .
C24 C 0.4978(2) 1.04921(15) 0.39385(15) 0.0722(6) Uani 1 1 d . . .
H24 H 0.5157 1.0846 0.4466 0.087 Uiso 1 1 calc R . .
C25 C 0.5999(2) 1.03381(14) 0.34987(13) 0.0627(5) Uani 1 1 d . . .
H25 H 0.6877 1.0586 0.3725 0.075 Uiso 1 1 calc R . .
C26 C 0.66380(16) 0.95462(13) 0.21742(12) 0.0516(4) Uani 1 1 d . . .
N1 N 0.57417(14) 0.98182(10) 0.27213(10) 0.0521(4) Uani 1 1 d . . .
O1 O 0.90105(14) 0.99540(10) 0.34637(9) 0.0718(4) Uani 1 1 d . . .
O2 O 0.12920(18) 0.07743(14) 0.47823(14) 0.0908(5) Uani 1 1 d . . .
P1 P 0.84076(4) 0.99090(3) 0.24520(3) 0.05181(19) Uani 1 1 d . . .
H2B H 0.118(3) 0.057(2) 0.540(3) 0.137(11) Uiso 1 1 d . . .
H2A H 0.059(4) 0.053(2) 0.436(3) 0.142(13) Uiso 1 1 d . . .


_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
C1 C2 1.384(3) . ?
C1 C6 1.385(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 P1 1.8011(18) . ?
C7 C12 1.391(3) . ?
C7 C8 1.399(2) . ?
C7 P1 1.7965(19) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.381(3) . ?
C13 C14 1.395(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.485(2) . ?
C19 C26 1.393(2) . ?
C19 C20 1.396(2) . ?
C20 C21 1.377(3) . ?
C20 H20 0.9300 . ?
C21 N1 1.399(2) . ?
C21 C22 1.415(2) . ?
C22 C23 1.346(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.419(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.352(3) . ?
C24 H24 0.9300 . ?
C25 N1 1.369(2) . ?
C25 H25 0.9300 . ?
C26 N1 1.404(2) . ?
C26 P1 1.7846(16) . ?
O1 P1 1.4917(14) . ?
O2 H2B 1.01(4) . ?
O2 H2A 0.89(4) . ?

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
C2 C1 C6 120.38(18) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.52(18) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.56(19) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.42(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 118.51(17) . . ?
C5 C6 P1 117.72(13) . . ?
C1 C6 P1 123.72(14) . . ?
C12 C7 C8 118.48(18) . . ?
C12 C7 P1 123.16(13) . . ?
C8 C7 P1 118.32(15) . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.86(19) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C18 C13 C14 119.7(2) . . ?
C18 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C13 118.90(19) . . ?
C17 C18 C19 119.35(17) . . ?
C13 C18 C19 121.68(19) . . ?
C26 C19 C20 108.03(16) . . ?
C26 C19 C18 128.73(14) . . ?
C20 C19 C18 123.24(16) . . ?
C21 C20 C19 109.04(16) . . ?
C21 C20 H20 125.5 . . ?
C19 C20 H20 125.5 . . ?
C20 C21 N1 107.29(15) . . ?
C20 C21 C22 134.90(18) . . ?
N1 C21 C22 117.78(19) . . ?
C23 C22 C21 120.80(19) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 119.64(18) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 120.4(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 N1 120.05(19) . . ?
C24 C25 H25 120.0 . . ?
N1 C25 H25 120.0 . . ?
C19 C26 N1 106.99(13) . . ?
C19 C26 P1 133.00(13) . . ?
N1 C26 P1 120.01(13) . . ?
C25 N1 C21 121.28(15) . . ?
C25 N1 C26 130.05(15) . . ?
C21 N1 C26 108.66(15) . . ?
H2B O2 H2A 107(3) . . ?
O1 P1 C26 112.48(8) . . ?
O1 P1 C7 111.55(8) . . ?
C26 P1 C7 106.97(8) . . ?
O1 P1 C6 111.00(8) . . ?
C26 P1 C6 106.91(8) . . ?
C7 P1 C6 107.65(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
C6 C1 C2 C3 -0.4(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 P1 -178.27(16) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C2 C1 C6 P1 178.25(16) . . . . ?
C12 C7 C8 C9 -0.8(3) . . . . ?
P1 C7 C8 C9 -178.88(15) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C8 C7 C12 C11 0.2(3) . . . . ?
P1 C7 C12 C11 178.15(14) . . . . ?
C10 C11 C12 C7 0.2(3) . . . . ?
C18 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C13 0.8(3) . . . . ?
C16 C17 C18 C19 177.73(19) . . . . ?
C14 C13 C18 C17 -0.9(3) . . . . ?
C14 C13 C18 C19 -177.81(19) . . . . ?
C17 C18 C19 C26 112.3(2) . . . . ?
C13 C18 C19 C26 -70.8(3) . . . . ?
C17 C18 C19 C20 -67.0(3) . . . . ?
C13 C18 C19 C20 109.9(2) . . . . ?
C26 C19 C20 C21 0.2(2) . . . . ?
C18 C19 C20 C21 179.63(17) . . . . ?
C19 C20 C21 N1 0.0(2) . . . . ?
C19 C20 C21 C22 -177.7(2) . . . . ?
C20 C21 C22 C23 177.6(2) . . . . ?
N1 C21 C22 C23 0.1(3) . . . . ?
C21 C22 C23 C24 0.8(3) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C23 C24 C25 N1 0.0(3) . . . . ?
C20 C19 C26 N1 -0.3(2) . . . . ?
C18 C19 C26 N1 -179.71(17) . . . . ?
C20 C19 C26 P1 -179.79(16) . . . . ?
C18 C19 C26 P1 0.8(3) . . . . ?
C24 C25 N1 C21 0.9(3) . . . . ?
C24 C25 N1 C26 -177.71(18) . . . . ?
C20 C21 N1 C25 -179.06(17) . . . . ?
C22 C21 N1 C25 -0.9(3) . . . . ?
C20 C21 N1 C26 -0.2(2) . . . . ?
C22 C21 N1 C26 177.95(17) . . . . ?
C19 C26 N1 C25 179.02(18) . . . . ?
P1 C26 N1 C25 -1.4(3) . . . . ?
C19 C26 N1 C21 0.30(19) . . . . ?
P1 C26 N1 C21 179.89(13) . . . . ?
C19 C26 P1 O1 -143.91(18) . . . . ?
N1 C26 P1 O1 36.63(17) . . . . ?
C19 C26 P1 C7 93.3(2) . . . . ?
N1 C26 P1 C7 -86.19(15) . . . . ?
C19 C26 P1 C6 -21.8(2) . . . . ?
N1 C26 P1 C6 158.71(13) . . . . ?
C12 C7 P1 O1 -128.88(15) . . . . ?
C8 C7 P1 O1 49.07(16) . . . . ?
C12 C7 P1 C26 -5.49(17) . . . . ?
C8 C7 P1 C26 172.46(14) . . . . ?
C12 C7 P1 C6 109.11(15) . . . . ?
C8 C7 P1 C6 -72.94(16) . . . . ?
C5 C6 P1 O1 47.23(16) . . . . ?
C1 C6 P1 O1 -130.25(16) . . . . ?
C5 C6 P1 C26 -75.77(15) . . . . ?
C1 C6 P1 C26 106.74(16) . . . . ?
C5 C6 P1 C7 169.58(14) . . . . ?
C1 C6 P1 C7 -7.90(17) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_a_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2162639'
loop_
_audit_author_name
_audit_author_address
'Ailong Shao'
;Fuyang Normal University
China
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 O3 P'
_chemical_formula_sum            'C17 H15 O3 P'
_chemical_formula_weight         298.26

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_space_group_name_Hall           '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   10.9372(5)
_cell_length_b                   9.5238(3)
_cell_length_c                   14.1492(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.251(4)
_cell_angle_gamma                90.00
_cell_volume                     1469.78(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3441
_cell_measurement_theta_min      2.273
_cell_measurement_theta_max      27.816

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9531
_exptl_absorpt_correction_T_max  0.9604
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6798
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2589
_reflns_number_gt                2108
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.3568P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2589
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.15823(18) 0.31693(18) 0.32450(14) 0.0424(5) Uani 1 1 d . . .
C2 C 0.12531(19) 0.4240(2) 0.38492(15) 0.0499(5) Uani 1 1 d . . .
H2 H 0.0757 0.4972 0.3614 0.060 Uiso 1 1 calc R . .
C3 C 0.1662(2) 0.4216(3) 0.47954(16) 0.0611(6) Uani 1 1 d . . .
H3 H 0.1435 0.4930 0.5195 0.073 Uiso 1 1 calc R . .
C4 C 0.2399(2) 0.3151(3) 0.51500(17) 0.0669(7) Uani 1 1 d . . .
H4 H 0.2674 0.3147 0.5788 0.080 Uiso 1 1 calc R . .
C5 C 0.2736(3) 0.2080(2) 0.45627(18) 0.0679(7) Uani 1 1 d . . .
H5 H 0.3241 0.1358 0.4803 0.081 Uiso 1 1 calc R . .
C6 C 0.2318(2) 0.2089(2) 0.36156(16) 0.0544(6) Uani 1 1 d . . .
H6 H 0.2534 0.1361 0.3223 0.065 Uiso 1 1 calc R . .
C7 C 0.22083(18) 0.31673(17) 0.12530(14) 0.0401(4) Uani 1 1 d . . .
C8 C 0.3439(2) 0.3096(2) 0.15553(16) 0.0553(6) Uani 1 1 d . . .
H8 H 0.3672 0.3026 0.2199 0.066 Uiso 1 1 calc R . .
C9 C 0.4325(2) 0.3128(3) 0.0907(2) 0.0706(7) Uani 1 1 d . . .
H9 H 0.5149 0.3072 0.1119 0.085 Uiso 1 1 calc R . .
C10 C 0.3999(2) 0.3242(2) -0.0041(2) 0.0670(7) Uani 1 1 d . . .
H10 H 0.4601 0.3269 -0.0472 0.080 Uiso 1 1 calc R . .
C11 C 0.2786(3) 0.3317(2) -0.03570(17) 0.0626(6) Uani 1 1 d . . .
H11 H 0.2563 0.3387 -0.1002 0.075 Uiso 1 1 calc R . .
C12 C 0.1893(2) 0.3290(2) 0.02860(15) 0.0520(5) Uani 1 1 d . . .
H12 H 0.1071 0.3354 0.0069 0.062 Uiso 1 1 calc R . .
C13 C 0.02717(17) 0.15142(19) 0.18444(13) 0.0404(4) Uani 1 1 d . . .
C14 C 0.04837(18) 0.0394(2) 0.12918(14) 0.0461(5) Uani 1 1 d . . .
H14 H 0.1106 0.0306 0.0882 0.055 Uiso 1 1 calc R . .
C15 C -0.0424(2) -0.0615(2) 0.14579(16) 0.0531(5) Uani 1 1 d . . .
H15 H -0.0509 -0.1497 0.1178 0.064 Uiso 1 1 calc R . .
C16 C -0.11447(18) -0.0063(2) 0.20977(14) 0.0460(5) Uani 1 1 d . . .
C17 C -0.2252(2) -0.0555(2) 0.25412(18) 0.0602(6) Uani 1 1 d . . .
H17A H -0.2493 -0.1471 0.2292 0.072 Uiso 1 1 calc R . .
H17B H -0.2078 -0.0639 0.3221 0.072 Uiso 1 1 calc R . .
O1 O 0.01342(14) 0.43899(14) 0.18149(11) 0.0572(4) Uani 1 1 d . . .
O2 O -0.32088(14) 0.0417(2) 0.23430(14) 0.0795(6) Uani 1 1 d . . .
H2A H -0.3820 0.0158 0.2597 0.119 Uiso 1 1 calc R . .
O3 O -0.07316(12) 0.12524(13) 0.23547(9) 0.0447(3) Uani 1 1 d . . .
P1 P 0.09813(4) 0.31935(5) 0.20295(4) 0.04030(17) Uani 1 1 d . . .


_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
C1 C6 1.385(3) . ?
C1 C2 1.395(3) . ?
C1 P1 1.795(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.384(3) . ?
C7 C12 1.391(3) . ?
C7 P1 1.7965(19) . ?
C8 C9 1.383(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.352(3) . ?
C13 O3 1.380(2) . ?
C13 P1 1.7885(18) . ?
C14 C15 1.414(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.350(3) . ?
C15 H15 0.9300 . ?
C16 O3 1.372(2) . ?
C16 C17 1.481(3) . ?
C17 O2 1.409(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
O1 P1 1.4856(14) . ?
O2 H2A 0.8200 . ?

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
C6 C1 C2 118.7(2) . . ?
C6 C1 P1 122.24(15) . . ?
C2 C1 P1 119.01(16) . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C8 C7 C12 118.22(19) . . ?
C8 C7 P1 124.43(16) . . ?
C12 C7 P1 117.29(15) . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 120.9(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 O3 109.69(16) . . ?
C14 C13 P1 134.32(15) . . ?
O3 C13 P1 115.98(12) . . ?
C13 C14 C15 106.72(18) . . ?
C13 C14 H14 126.6 . . ?
C15 C14 H14 126.6 . . ?
C16 C15 C14 107.35(18) . . ?
C16 C15 H15 126.3 . . ?
C14 C15 H15 126.3 . . ?
C15 C16 O3 109.65(17) . . ?
C15 C16 C17 134.22(19) . . ?
O3 C16 C17 116.11(18) . . ?
O2 C17 C16 109.06(18) . . ?
O2 C17 H17A 109.9 . . ?
C16 C17 H17A 109.9 . . ?
O2 C17 H17B 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C17 O2 H2A 109.5 . . ?
C16 O3 C13 106.58(14) . . ?
O1 P1 C13 113.49(9) . . ?
O1 P1 C7 111.63(9) . . ?
C13 P1 C7 103.52(8) . . ?
O1 P1 C1 112.59(9) . . ?
C13 P1 C1 104.65(9) . . ?
C7 P1 C1 110.40(9) . . ?

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
C6 C1 C2 C3 0.3(3) . . . . ?
P1 C1 C2 C3 177.38(15) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
P1 C1 C6 C5 -178.02(17) . . . . ?
C12 C7 C8 C9 -0.8(3) . . . . ?
P1 C7 C8 C9 -177.82(17) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C7 -0.9(3) . . . . ?
C8 C7 C12 C11 1.0(3) . . . . ?
P1 C7 C12 C11 178.22(15) . . . . ?
O3 C13 C14 C15 0.1(2) . . . . ?
P1 C13 C14 C15 -179.01(17) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C14 C15 C16 O3 -0.5(2) . . . . ?
C14 C15 C16 C17 178.0(2) . . . . ?
C15 C16 C17 O2 -121.7(3) . . . . ?
O3 C16 C17 O2 56.7(3) . . . . ?
C15 C16 O3 C13 0.6(2) . . . . ?
C17 C16 O3 C13 -178.26(18) . . . . ?
C14 C13 O3 C16 -0.4(2) . . . . ?
P1 C13 O3 C16 178.88(13) . . . . ?
C14 C13 P1 O1 121.1(2) . . . . ?
O3 C13 P1 O1 -57.97(16) . . . . ?
C14 C13 P1 C7 -0.1(2) . . . . ?
O3 C13 P1 C7 -179.16(13) . . . . ?
C14 C13 P1 C1 -115.8(2) . . . . ?
O3 C13 P1 C1 65.16(15) . . . . ?
C8 C7 P1 O1 127.82(17) . . . . ?
C12 C7 P1 O1 -49.21(17) . . . . ?
C8 C7 P1 C13 -109.74(17) . . . . ?
C12 C7 P1 C13 73.23(16) . . . . ?
C8 C7 P1 C1 1.78(19) . . . . ?
C12 C7 P1 C1 -175.25(14) . . . . ?
C6 C1 P1 O1 175.16(16) . . . . ?
C2 C1 P1 O1 -1.83(18) . . . . ?
C6 C1 P1 C13 51.45(18) . . . . ?
C2 C1 P1 C13 -125.54(15) . . . . ?
C6 C1 P1 C7 -59.34(18) . . . . ?
C2 C1 P1 C7 123.67(15) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_a_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2162642'
loop_
_audit_author_name
_audit_author_address
'Ailong Shao'
;Fuyang Normal University
China
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H19 O P'
_chemical_formula_sum            'C26 H19 O P'
_chemical_formula_weight         378.38

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.6908(4)
_cell_length_b                   9.4451(3)
_cell_length_c                   16.5679(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.759(4)
_cell_angle_gamma                90.00
_cell_volume                     1951.02(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5152
_cell_measurement_theta_min      2.4970
_cell_measurement_theta_max      29.3280

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9566
_exptl_absorpt_correction_T_max  0.9639
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9222
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3419
_reflns_number_gt                2820
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0868P)²+0.0819P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3419
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1343
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.48564(15) 0.62726(19) 0.09315(12) 0.0443(5) Uani 1 1 d . . .
H1 H 0.5440 0.6113 0.0677 0.053 Uiso 1 1 calc R . .
C2 C 0.38559(15) 0.61145(19) 0.04923(12) 0.0461(5) Uani 1 1 d . . .
H2 H 0.3764 0.5866 -0.0060 0.055 Uiso 1 1 calc R . .
C3 C 0.29346(14) 0.63211(17) 0.08592(12) 0.0415(4) Uani 1 1 d . . .
C4 C 0.18971(14) 0.61387(19) 0.03954(13) 0.0483(5) Uani 1 1 d . . .
H4 H 0.1812 0.5854 -0.0150 0.058 Uiso 1 1 calc R . .
C5 C 0.10142(16) 0.6375(2) 0.07358(15) 0.0561(6) Uani 1 1 d . . .
H5 H 0.0332 0.6270 0.0420 0.067 Uiso 1 1 calc R . .
C6 C 0.11365(16) 0.6773(2) 0.15570(16) 0.0564(6) Uani 1 1 d . . .
H6 H 0.0532 0.6921 0.1789 0.068 Uiso 1 1 calc R . .
C7 C 0.21356(15) 0.6949(2) 0.20268(14) 0.0506(5) Uani 1 1 d . . .
H7 H 0.2201 0.7210 0.2575 0.061 Uiso 1 1 calc R . .
C8 C 0.30684(14) 0.67413(17) 0.16907(12) 0.0403(4) Uani 1 1 d . . .
C9 C 0.41480(14) 0.69487(17) 0.21621(12) 0.0407(4) Uani 1 1 d . . .
C10 C 0.43375(16) 0.7428(2) 0.29776(13) 0.0533(5) Uani 1 1 d . . .
H10 H 0.3757 0.7637 0.3226 0.064 Uiso 1 1 calc R . .
C11 C 0.53519(16) 0.7594(2) 0.34147(14) 0.0601(6) Uani 1 1 d . . .
H11 H 0.5455 0.7897 0.3958 0.072 Uiso 1 1 calc R . .
C12 C 0.62407(16) 0.7310(2) 0.30489(13) 0.0514(5) Uani 1 1 d . . .
H12 H 0.6930 0.7428 0.3352 0.062 Uiso 1 1 calc R . .
C13 C 0.61036(14) 0.68590(18) 0.22472(12) 0.0406(4) Uani 1 1 d . . .
C14 C 0.50442(14) 0.66820(17) 0.17823(12) 0.0394(4) Uani 1 1 d . . .
C15 C 0.67227(19) 0.9151(2) 0.10241(15) 0.0642(6) Uani 1 1 d . . .
H15 H 0.6286 0.9315 0.1407 0.077 Uiso 1 1 calc R . .
C16 C 0.6797(2) 1.0154(2) 0.04267(18) 0.0805(8) Uani 1 1 d . . .
H16 H 0.6396 1.0983 0.0403 0.097 Uiso 1 1 calc R . .
C17 C 0.7458(2) 0.9931(2) -0.01305(16) 0.0745(7) Uani 1 1 d . . .
H17 H 0.7511 1.0617 -0.0524 0.089 Uiso 1 1 calc R . .
C18 C 0.8039(2) 0.8710(2) -0.01105(15) 0.0651(6) Uani 1 1 d . . .
H18 H 0.8485 0.8564 -0.0489 0.078 Uiso 1 1 calc R . .
C19 C 0.79599(16) 0.7694(2) 0.04741(13) 0.0528(5) Uani 1 1 d . . .
H19 H 0.8351 0.6859 0.0483 0.063 Uiso 1 1 calc R . .
C20 C 0.73046(14) 0.78979(18) 0.10498(12) 0.0431(4) Uani 1 1 d . . .
C21 C 0.84473(14) 0.67272(16) 0.25626(11) 0.0383(4) Uani 1 1 d . . .
C22 C 0.89825(16) 0.55144(19) 0.28792(13) 0.0502(5) Uani 1 1 d . . .
H22 H 0.8696 0.4632 0.2714 0.060 Uiso 1 1 calc R . .
C23 C 0.99334(18) 0.5596(2) 0.34353(14) 0.0613(6) Uani 1 1 d . . .
H23 H 1.0282 0.4771 0.3645 0.074 Uiso 1 1 calc R . .
C24 C 1.03687(17) 0.6890(2) 0.36815(14) 0.0575(6) Uani 1 1 d . . .
H24 H 1.1017 0.6944 0.4050 0.069 Uiso 1 1 calc R . .
C25 C 0.98440(17) 0.8103(2) 0.33830(14) 0.0582(6) Uani 1 1 d . . .
H25 H 1.0134 0.8981 0.3556 0.070 Uiso 1 1 calc R . .
C26 C 0.88861(16) 0.80342(19) 0.28264(13) 0.0502(5) Uani 1 1 d . . .
H26 H 0.8535 0.8863 0.2628 0.060 Uiso 1 1 calc R . .
O1 O 0.72634(10) 0.50705(12) 0.14066(8) 0.0469(4) Uani 1 1 d . . .
P1 P 0.72588(4) 0.64970(4) 0.17836(3) 0.03858(19) Uani 1 1 d . . .


_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
C1 C2 1.349(3) . ?
C1 C14 1.438(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.428(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.406(3) . ?
C3 C8 1.413(3) . ?
C4 C5 1.363(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.413(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.458(3) . ?
C9 C10 1.402(3) . ?
C9 C14 1.421(2) . ?
C10 C11 1.363(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.402(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.429(3) . ?
C13 P1 1.8102(18) . ?
C15 C16 1.386(3) . ?
C15 C20 1.392(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.391(3) . ?
C19 H19 0.9300 . ?
C20 P1 1.8051(19) . ?
C21 C22 1.384(2) . ?
C21 C26 1.391(2) . ?
C21 P1 1.8059(19) . ?
C22 C23 1.377(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.372(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
O1 P1 1.4856(12) . ?

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
C2 C1 C14 121.72(17) . . ?
C2 C1 H1 119.1 . . ?
C14 C1 H1 119.1 . . ?
C1 C2 C3 121.22(18) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C8 119.82(17) . . ?
C4 C3 C2 120.54(18) . . ?
C8 C3 C2 119.62(17) . . ?
C5 C4 C3 120.79(19) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.75(19) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.9(2) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C3 C8 C7 117.79(18) . . ?
C3 C8 C9 119.33(16) . . ?
C7 C8 C9 122.88(18) . . ?
C10 C9 C14 118.44(17) . . ?
C10 C9 C8 122.31(17) . . ?
C14 C9 C8 119.25(17) . . ?
C11 C10 C9 121.61(18) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.29(19) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.65(19) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.59(17) . . ?
C12 C13 P1 120.13(15) . . ?
C14 C13 P1 120.27(14) . . ?
C9 C14 C13 119.38(17) . . ?
C9 C14 C1 118.80(17) . . ?
C13 C14 C1 121.80(16) . . ?
C16 C15 C20 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C20 C15 H15 120.1 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.6(2) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 121.1(2) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C15 C20 C19 118.60(18) . . ?
C15 C20 P1 124.09(16) . . ?
C19 C20 P1 117.31(13) . . ?
C22 C21 C26 118.44(17) . . ?
C22 C21 P1 117.16(13) . . ?
C26 C21 P1 124.29(13) . . ?
C23 C22 C21 120.94(17) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C24 C23 C22 120.17(18) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.8(2) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.55(18) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 120.13(17) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
O1 P1 C20 112.24(8) . . ?
O1 P1 C21 109.96(7) . . ?
C20 P1 C21 105.40(8) . . ?
O1 P1 C13 114.63(8) . . ?
C20 P1 C13 106.13(8) . . ?
C21 P1 C13 107.97(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
C14 C1 C2 C3 -1.2(3) . . . . ?
C1 C2 C3 C4 -179.37(16) . . . . ?
C1 C2 C3 C8 2.0(3) . . . . ?
C8 C3 C4 C5 0.6(3) . . . . ?
C2 C3 C4 C5 -178.06(17) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C4 C3 C8 C7 0.6(2) . . . . ?
C2 C3 C8 C7 179.30(16) . . . . ?
C4 C3 C8 C9 -179.04(15) . . . . ?
C2 C3 C8 C9 -0.4(2) . . . . ?
C6 C7 C8 C3 -1.1(3) . . . . ?
C6 C7 C8 C9 178.54(16) . . . . ?
C3 C8 C9 C10 177.00(17) . . . . ?
C7 C8 C9 C10 -2.7(3) . . . . ?
C3 C8 C9 C14 -1.9(2) . . . . ?
C7 C8 C9 C14 178.44(15) . . . . ?
C14 C9 C10 C11 -2.2(3) . . . . ?
C8 C9 C10 C11 178.90(19) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C11 C12 C13 P1 180.00(15) . . . . ?
C10 C9 C14 C13 2.2(3) . . . . ?
C8 C9 C14 C13 -178.85(14) . . . . ?
C10 C9 C14 C1 -176.32(16) . . . . ?
C8 C9 C14 C1 2.6(2) . . . . ?
C12 C13 C14 C9 -1.3(3) . . . . ?
P1 C13 C14 C9 178.93(12) . . . . ?
C12 C13 C14 C1 177.23(17) . . . . ?
P1 C13 C14 C1 -2.6(2) . . . . ?
C2 C1 C14 C9 -1.1(3) . . . . ?
C2 C1 C14 C13 -179.59(17) . . . . ?
C20 C15 C16 C17 -1.3(4) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C16 C15 C20 C19 0.7(3) . . . . ?
C16 C15 C20 P1 -178.8(2) . . . . ?
C18 C19 C20 C15 0.2(3) . . . . ?
C18 C19 C20 P1 179.80(17) . . . . ?
C26 C21 C22 C23 -0.7(3) . . . . ?
P1 C21 C22 C23 175.70(17) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C22 C23 C24 C25 1.1(3) . . . . ?
C23 C24 C25 C26 -0.9(3) . . . . ?
C22 C21 C26 C25 1.0(3) . . . . ?
P1 C21 C26 C25 -175.18(16) . . . . ?
C24 C25 C26 C21 -0.2(3) . . . . ?
C15 C20 P1 O1 140.34(18) . . . . ?
C19 C20 P1 O1 -39.19(18) . . . . ?
C15 C20 P1 C21 -99.98(19) . . . . ?
C19 C20 P1 C21 80.49(16) . . . . ?
C15 C20 P1 C13 14.4(2) . . . . ?
C19 C20 P1 C13 -165.13(15) . . . . ?
C22 C21 P1 O1 -19.70(17) . . . . ?
C26 C21 P1 O1 156.49(16) . . . . ?
C22 C21 P1 C20 -140.88(15) . . . . ?
C26 C21 P1 C20 35.31(18) . . . . ?
C22 C21 P1 C13 106.03(15) . . . . ?
C26 C21 P1 C13 -77.78(18) . . . . ?
C12 C13 P1 O1 126.58(16) . . . . ?
C14 C13 P1 O1 -53.61(16) . . . . ?
C12 C13 P1 C20 -108.95(16) . . . . ?
C14 C13 P1 C20 70.86(15) . . . . ?
C12 C13 P1 C21 3.65(18) . . . . ?
C14 C13 P1 C21 -176.54(13) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.053
