# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

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

data_01-073
_database_code_depnum_ccdc_archive 'CCDC 2372952'
loop_
_audit_author_name
_audit_author_address
'Wei Ding'
;Zhengzhou University
China
;
_audit_update_record             
;
2024-07-23 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_audit_creation_date             2023-06-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 F3 N O2 P'
_chemical_formula_sum            'C23 H19 F3 N O2 P'
_chemical_formula_weight         429.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H P N O F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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                   13.2823(3)
_cell_length_b                   10.2123(2)
_cell_length_c                   17.0172(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.613(2)
_cell_angle_gamma                90
_cell_volume                     2130.81(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5532
_cell_measurement_temperature    119.99(15)
_cell_measurement_theta_max      69.8450
_cell_measurement_theta_min      3.6520
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    1.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10037
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.020
_diffrn_reflns_theta_min         3.621
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00  50.00   0.50    0.50    --    0.00 -82.00 -60.00   50
  2  ω     20.00  48.00   0.50    0.50    --    0.00 -82.00-150.00   56
  3  ω    -32.00  -2.00   0.50    0.50    --    0.00 -82.00  30.00   60
  4  ω    -14.00  18.00   0.50    0.50    --    0.00 -82.00 -60.00   64
  5  ω    101.00 128.00   0.50    0.50    --   53.20  82.00 120.00   54
  6  ω     94.00 143.00   0.50    0.50    --   53.20  82.00  30.00   98
  7  ω     25.00 134.00   0.50    0.50    --   53.20  61.00 150.00  218
  8  ω     98.00 134.00   0.50    0.50    --   53.20  77.00  90.00   72
  9  ω     10.00  79.00   0.50    0.50    --   53.20  61.00-180.00  138
 10  ω    104.00 142.00   0.50    0.50    --   53.20  61.00-180.00   76
 11  ω    105.00 132.00   0.50    0.50    --   53.20  77.00 -90.00   54
 12  ω     80.00 141.00   0.50    0.50    --   53.20  77.00   0.00  122
 13  ω     94.00 119.00   0.50    0.50    --   53.20  82.00  60.00   50
 14  ω     18.00 149.00   0.50    0.50    --  106.50 -54.00  90.00  262
 15  ω     94.00 148.00   0.50    0.50    --  106.50 -65.00 -90.00  108
 16  ω    105.00 185.00   0.50    0.50    --  106.50 -32.00 -90.00  160
 17  ω     89.00 115.00   0.50    0.50    --  106.50  82.00 150.00   52
 18  ω     27.00  96.00   0.50    0.50    --  106.50 -32.00 -90.00  138
 19  ω     52.00 140.00   0.50    0.50    --  106.50 -43.00  90.00  176
 20  ω    153.00 178.00   0.50    0.50    --  106.50  82.00 150.00   50
 21  ω     22.00 145.00   0.50    0.50    --  106.50 -82.00 -90.00  246
 22  ω     26.00  90.00   0.50    0.50    --  106.50 -65.00 -90.00  128
 23  ω     49.00 135.00   0.50    0.50    --  106.50 -82.00 120.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0125031000
_diffrn_orient_matrix_UB_12      0.0665172000
_diffrn_orient_matrix_UB_13      -0.0769714000
_diffrn_orient_matrix_UB_21      0.1231503000
_diffrn_orient_matrix_UB_22      -0.0298187000
_diffrn_orient_matrix_UB_23      0.0379584000
_diffrn_orient_matrix_UB_31      -0.0215418000
_diffrn_orient_matrix_UB_32      -0.1321417000
_diffrn_orient_matrix_UB_33      -0.0473533000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3343
_reflns_number_total             3979
_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       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3979
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.8034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1048
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F3-C7 \\sim F5-C7
 with sigma of 0.02
 C7-F2 \\sim C7-F6
 with sigma of 0.02
 C7-F1 \\sim C7-F4
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F4, F5, F6, C1, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.003
 F1, F2, F3, C1, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F4)=Sof(F5)=Sof(F6)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.61405(3) 0.23272(4) 0.41434(3) 0.01645(12) Uani 1 1 d . . . . .
F1 F 0.5109(6) 0.3416(10) 0.9793(2) 0.114(3) Uani 0.520(9) 1 d D . P A 1
F2 F 0.6753(5) 0.3237(9) 1.0050(3) 0.091(3) Uani 0.520(9) 1 d D . P A 1
F3 F 0.5806(10) 0.1606(5) 1.0081(3) 0.115(4) Uani 0.520(9) 1 d D . P A 1
F4 F 0.5271(5) 0.2144(9) 0.9986(4) 0.079(3) Uani 0.480(9) 1 d D . P A 2
F5 F 0.6872(5) 0.2147(11) 1.0104(2) 0.101(3) Uani 0.480(9) 1 d D . P A 2
F6 F 0.5968(10) 0.3869(5) 0.9860(3) 0.109(4) Uani 0.480(9) 1 d D . P A 2
O1 O 0.49117(11) 0.37385(12) 0.56900(8) 0.0238(3) Uani 1 1 d . . . . .
O2 O 0.61671(10) 0.08823(11) 0.40161(7) 0.0216(3) Uani 1 1 d . . . . .
N1 N 0.47528(13) 0.16788(15) 0.61381(9) 0.0202(3) Uani 1 1 d . . . . .
H1 H 0.4493(17) 0.089(2) 0.5974(13) 0.026(5) Uiso 1 1 d . . . . .
C1 C 0.55638(16) 0.2414(2) 0.87316(11) 0.0283(4) Uani 1 1 d . . . . .
C2 C 0.47807(16) 0.14900(19) 0.83095(11) 0.0259(4) Uani 1 1 d . . . . .
H2 H 0.442899 0.100732 0.860833 0.031 Uiso 1 1 calc R U . . .
C3 C 0.45116(15) 0.12714(17) 0.74483(11) 0.0214(4) Uani 1 1 d . . . . .
H3 H 0.397176 0.064041 0.715608 0.026 Uiso 1 1 calc R U . . .
C4 C 0.50309(14) 0.19749(17) 0.70096(10) 0.0196(4) Uani 1 1 d . . . . .
C5 C 0.58263(15) 0.28993(19) 0.74384(11) 0.0254(4) Uani 1 1 d . . . . .
H5 H 0.618813 0.337647 0.714486 0.030 Uiso 1 1 calc R U . . .
C6 C 0.60818(16) 0.3113(2) 0.82985(12) 0.0295(4) Uani 1 1 d . . . . .
H6 H 0.661851 0.374518 0.859368 0.035 Uiso 1 1 calc R U . . .
C7 C 0.5859(2) 0.2658(2) 0.96619(13) 0.0404(5) Uani 1 1 d D . . . .
C8 C 0.47155(13) 0.25731(17) 0.55357(10) 0.0178(3) Uani 1 1 d . . . . .
C9 C 0.44177(14) 0.20650(17) 0.46440(10) 0.0176(3) Uani 1 1 d . . . . .
C10 C 0.38515(15) 0.09789(18) 0.43592(11) 0.0226(4) Uani 1 1 d . . . . .
H10A H 0.3592(16) 0.042(2) 0.4701(13) 0.025(5) Uiso 1 1 d . . . . .
H10B H 0.3639(15) 0.0703(19) 0.3772(13) 0.024(5) Uiso 1 1 d . . . . .
C11 C 0.48148(14) 0.28949(17) 0.40867(10) 0.0189(4) Uani 1 1 d . . . . .
H11A H 0.487173 0.381914 0.427452 0.023 Uiso 1 1 calc R U . . .
H11B H 0.428281 0.285051 0.349026 0.023 Uiso 1 1 calc R U . . .
C12 C 0.63852(13) 0.32051(17) 0.33140(10) 0.0182(4) Uani 1 1 d . . . . .
C13 C 0.66470(14) 0.24747(18) 0.27248(11) 0.0210(4) Uani 1 1 d . . . . .
H13 H 0.673279 0.155238 0.278911 0.025 Uiso 1 1 calc R U . . .
C14 C 0.67822(15) 0.30919(19) 0.20462(11) 0.0245(4) Uani 1 1 d . . . . .
H14 H 0.695752 0.259159 0.164550 0.029 Uiso 1 1 calc R U . . .
C15 C 0.66616(15) 0.44401(19) 0.19515(11) 0.0245(4) Uani 1 1 d . . . . .
H15 H 0.674939 0.486205 0.148437 0.029 Uiso 1 1 calc R U . . .
C16 C 0.64126(15) 0.51695(18) 0.25405(12) 0.0260(4) Uani 1 1 d . . . . .
H16 H 0.633520 0.609266 0.247737 0.031 Uiso 1 1 calc R U . . .
C17 C 0.62757(15) 0.45589(18) 0.32222(11) 0.0245(4) Uani 1 1 d . . . . .
H17 H 0.610770 0.506371 0.362487 0.029 Uiso 1 1 calc R U . . .
C18 C 0.71469(14) 0.28154(17) 0.51612(10) 0.0186(3) Uani 1 1 d . . . . .
C19 C 0.71370(15) 0.40488(18) 0.55180(11) 0.0230(4) Uani 1 1 d . . . . .
H19 H 0.658131 0.466349 0.522779 0.028 Uiso 1 1 calc R U . . .
C20 C 0.79440(16) 0.43656(19) 0.62975(11) 0.0279(4) Uani 1 1 d . . . . .
H20 H 0.793899 0.520036 0.654232 0.033 Uiso 1 1 calc R U . . .
C21 C 0.87557(16) 0.3477(2) 0.67213(12) 0.0319(5) Uani 1 1 d . . . . .
H21 H 0.930917 0.370606 0.725316 0.038 Uiso 1 1 calc R U . . .
C22 C 0.87650(16) 0.2258(2) 0.63745(13) 0.0323(5) Uani 1 1 d . . . . .
H22 H 0.931865 0.164465 0.667120 0.039 Uiso 1 1 calc R U . . .
C23 C 0.79656(15) 0.19279(19) 0.55921(12) 0.0256(4) Uani 1 1 d . . . . .
H23 H 0.797852 0.109244 0.535064 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.4938(12) . ?
P1 C11 1.8208(17) . ?
P1 C12 1.8039(17) . ?
P1 C18 1.8041(17) . ?
F1 C7 1.347(5) . ?
F2 C7 1.262(4) . ?
F3 C7 1.307(5) . ?
F4 C7 1.233(5) . ?
F5 C7 1.367(5) . ?
F6 C7 1.276(5) . ?
O1 C8 1.225(2) . ?
N1 H1 0.88(2) . ?
N1 C4 1.416(2) . ?
N1 C8 1.360(2) . ?
C1 C2 1.384(3) . ?
C1 C6 1.384(3) . ?
C1 C7 1.498(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(2) . ?
C4 C5 1.395(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
C8 C9 1.506(2) . ?
C9 C10 1.323(3) . ?
C9 C11 1.510(2) . ?
C10 H10A 0.97(2) . ?
C10 H10B 0.97(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.397(2) . ?
C12 C17 1.393(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.401(2) . ?
C18 C23 1.389(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.380(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.388(3) . ?
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
O2 P1 C11 112.53(8) . . ?
O2 P1 C12 110.86(7) . . ?
O2 P1 C18 111.23(8) . . ?
C12 P1 C11 105.18(8) . . ?
C12 P1 C18 108.90(8) . . ?
C18 P1 C11 107.90(8) . . ?
C4 N1 H1 116.2(13) . . ?
C8 N1 H1 118.7(13) . . ?
C8 N1 C4 124.43(15) . . ?
C2 C1 C6 120.23(17) . . ?
C2 C1 C7 120.06(18) . . ?
C6 C1 C7 119.72(18) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.69(17) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.22(17) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 N1 117.84(16) . . ?
C3 C4 C5 119.96(16) . . ?
C5 C4 N1 122.15(16) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.14(17) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 120.75(18) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
F1 C7 C1 111.1(3) . . ?
F2 C7 F1 104.5(4) . . ?
F2 C7 F3 109.7(5) . . ?
F2 C7 C1 116.2(2) . . ?
F3 C7 F1 100.6(4) . . ?
F3 C7 C1 113.2(3) . . ?
F4 C7 F5 104.5(4) . . ?
F4 C7 F6 108.7(4) . . ?
F4 C7 C1 116.6(3) . . ?
F5 C7 C1 108.7(3) . . ?
F6 C7 F5 103.7(5) . . ?
F6 C7 C1 113.4(3) . . ?
O1 C8 N1 123.23(15) . . ?
O1 C8 C9 120.17(15) . . ?
N1 C8 C9 116.60(15) . . ?
C8 C9 C11 114.81(14) . . ?
C10 C9 C8 123.38(15) . . ?
C10 C9 C11 121.81(15) . . ?
C9 C10 H10A 123.9(12) . . ?
C9 C10 H10B 121.3(12) . . ?
H10A C10 H10B 114.7(17) . . ?
P1 C11 H11A 109.5 . . ?
P1 C11 H11B 109.5 . . ?
C9 C11 P1 110.62(11) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 P1 117.76(13) . . ?
C17 C12 P1 122.59(13) . . ?
C17 C12 C13 119.58(15) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.18(17) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.10(16) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.84(16) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.44(17) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 120.1 . . ?
C16 C17 C12 119.85(16) . . ?
C16 C17 H17 120.1 . . ?
C19 C18 P1 122.53(13) . . ?
C23 C18 P1 117.86(13) . . ?
C23 C18 C19 119.60(16) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.49(17) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.51(18) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.19(18) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.00(18) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.19(18) . . ?
C22 C23 H23 119.9 . . ?

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
P1 C12 C13 C14 176.32(14) . . . . ?
P1 C12 C17 C16 -176.19(14) . . . . ?
P1 C18 C19 C20 -179.14(14) . . . . ?
P1 C18 C23 C22 179.51(15) . . . . ?
O1 C8 C9 C10 -156.22(18) . . . . ?
O1 C8 C9 C11 23.7(2) . . . . ?
O2 P1 C11 C9 49.20(13) . . . . ?
O2 P1 C12 C13 -5.01(16) . . . . ?
O2 P1 C12 C17 172.11(14) . . . . ?
O2 P1 C18 C19 -165.61(13) . . . . ?
O2 P1 C18 C23 15.36(16) . . . . ?
N1 C4 C5 C6 -178.04(17) . . . . ?
N1 C8 C9 C10 23.9(2) . . . . ?
N1 C8 C9 C11 -156.15(15) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C7 F1 -78.7(6) . . . . ?
C2 C1 C7 F2 162.0(6) . . . . ?
C2 C1 C7 F3 33.6(7) . . . . ?
C2 C1 C7 F4 -10.1(6) . . . . ?
C2 C1 C7 F5 107.7(6) . . . . ?
C2 C1 C7 F6 -137.5(7) . . . . ?
C2 C3 C4 N1 177.77(17) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 N1 C8 O1 -0.7(3) . . . . ?
C4 N1 C8 C9 179.15(16) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C6 C1 C7 F1 101.7(6) . . . . ?
C6 C1 C7 F2 -17.7(6) . . . . ?
C6 C1 C7 F3 -146.0(6) . . . . ?
C6 C1 C7 F4 170.3(5) . . . . ?
C6 C1 C7 F5 -71.9(6) . . . . ?
C6 C1 C7 F6 42.8(7) . . . . ?
C7 C1 C2 C3 179.97(19) . . . . ?
C7 C1 C6 C5 179.6(2) . . . . ?
C8 N1 C4 C3 145.82(17) . . . . ?
C8 N1 C4 C5 -36.7(3) . . . . ?
C8 C9 C11 P1 92.33(15) . . . . ?
C10 C9 C11 P1 -87.74(18) . . . . ?
C11 P1 C12 C13 -126.90(14) . . . . ?
C11 P1 C12 C17 50.23(17) . . . . ?
C11 P1 C18 C19 -41.74(16) . . . . ?
C11 P1 C18 C23 139.23(14) . . . . ?
C12 P1 C11 C9 169.99(12) . . . . ?
C12 P1 C18 C19 71.92(16) . . . . ?
C12 P1 C18 C23 -107.11(15) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C12 C17 C16 0.9(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C17 C12 C13 C14 -0.9(3) . . . . ?
C18 P1 C11 C9 -73.88(13) . . . . ?
C18 P1 C12 C13 117.67(14) . . . . ?
C18 P1 C12 C17 -65.20(17) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C18 C23 C22 0.4(3) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C20 C21 C22 C23 0.9(3) . . . . ?
C21 C22 C23 C18 -0.8(3) . . . . ?
C23 C18 C19 C20 -0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.742
####################################################################### 
# 
# 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_1-64
_database_code_depnum_ccdc_archive 'CCDC 2372953'
loop_
_audit_author_name
_audit_author_address
'Wei Ding'
;Zhengzhou University
China
;
_audit_update_record             
;
2024-07-23 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_audit_creation_date             2023-06-02
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 O3 P'
_chemical_formula_sum            'C23 H21 O3 P'
_chemical_formula_weight         376.37
_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'

_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                   11.7326(12)
_cell_length_b                   5.7350(7)
_cell_length_c                   29.594(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.789(10)
_cell_angle_gamma                90
_cell_volume                     1991.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2940
_cell_measurement_temperature    293.0(3)
_cell_measurement_theta_max      26.0300
_cell_measurement_theta_min      2.6780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9099
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.680
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  61.00   1.00    3.91    --  -11.27  57.00-150.00   75
  2  ω    -81.00  10.00   1.00    3.91    --  -11.27 -19.00  60.00   91
  3  ω     47.00  96.00   1.00    3.91    --   11.90-178.00  60.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0374663000
_diffrn_orient_matrix_UB_12      0.0727976000
_diffrn_orient_matrix_UB_13      0.0126444000
_diffrn_orient_matrix_UB_21      0.0313318000
_diffrn_orient_matrix_UB_22      0.0235626000
_diffrn_orient_matrix_UB_23      -0.0198276000
_diffrn_orient_matrix_UB_31      -0.0356427000
_diffrn_orient_matrix_UB_32      0.0971170000
_diffrn_orient_matrix_UB_33      -0.0046789000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2797
_reflns_number_total             3501
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3501
_refine_ls_number_restraints     196
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.099
_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)+(0.0549P)²+0.7989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1330
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 P1, O1, O2, O3, C1, C2, H2, C3, H3, C4, H4, C5, H5, C6, H6, C7, H7A, H7B, C8,
 C9, C10, H10A, H10B, C11, H11A, H11B, C12, C13, H13, C14, H14, C15, H15, C16,
 H16, C17, H17, C18, C19, H19, C20, H20, C21, H21, C22, H22, C23, H23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.41926(5) 0.49324(10) 0.38595(2) 0.0390(2) Uani 1 1 d . . . . .
O1 O 0.44849(15) 0.2442(3) 0.37949(6) 0.0548(5) Uani 1 1 d . . . . .
O2 O 0.6362(2) 0.4040(4) 0.26994(7) 0.0850(7) Uani 1 1 d . . . . .
O3 O 0.70990(15) 0.3996(3) 0.34030(6) 0.0623(5) Uani 1 1 d . . . . .
C1 C 0.8694(2) 0.1724(5) 0.36434(10) 0.0594(6) Uani 1 1 d . . . . .
C2 C 0.9507(3) 0.3369(5) 0.37513(13) 0.0760(8) Uani 1 1 d . . . . .
H2 H 0.953405 0.477678 0.358258 0.091 Uiso 1 1 calc R U . . .
C3 C 1.0278(3) 0.3024(7) 0.40957(15) 0.0928(10) Uani 1 1 d . . . . .
H3 H 1.082975 0.418776 0.416505 0.111 Uiso 1 1 calc R U . . .
C4 C 1.0254(3) 0.1014(7) 0.43386(13) 0.0889(10) Uani 1 1 d . . . . .
H4 H 1.079202 0.077434 0.457707 0.107 Uiso 1 1 calc R U . . .
C5 C 0.9466(3) -0.0655(6) 0.42422(12) 0.0823(9) Uani 1 1 d . . . . .
H5 H 0.944970 -0.205496 0.441348 0.099 Uiso 1 1 calc R U . . .
C6 C 0.8683(3) -0.0306(5) 0.38921(12) 0.0720(8) Uani 1 1 d . . . . .
H6 H 0.813490 -0.147773 0.382369 0.086 Uiso 1 1 calc R U . . .
C7 C 0.7867(3) 0.2139(7) 0.32654(12) 0.0892(11) Uani 1 1 d . . . . .
H7A H 0.827705 0.260172 0.298923 0.107 Uiso 1 1 calc R U . . .
H7B H 0.743049 0.069924 0.319937 0.107 Uiso 1 1 calc R U . . .
C8 C 0.6384(2) 0.4788(5) 0.30792(9) 0.0557(6) Uani 1 1 d . . . . .
C9 C 0.5673(2) 0.6757(5) 0.32440(8) 0.0497(6) Uani 1 1 d . . . . .
C10 C 0.5338(3) 0.8357(7) 0.29509(13) 0.0807(10) Uani 1 1 d . . . . .
H10A H 0.553(3) 0.817(5) 0.2654(11) 0.083(10) Uiso 1 1 d . . . . .
H10B H 0.489(3) 0.982(6) 0.3057(12) 0.101(11) Uiso 1 1 d . . . . .
C11 C 0.5352(2) 0.6906(5) 0.37348(8) 0.0431(6) Uani 1 1 d . . . . .
H11A H 0.595(2) 0.644(4) 0.3928(8) 0.049(7) Uiso 1 1 d . . . . .
H11B H 0.512(2) 0.841(5) 0.3799(8) 0.054(7) Uiso 1 1 d . . . . .
C12 C 0.37531(19) 0.5584(4) 0.44285(8) 0.0428(5) Uani 1 1 d . . . . .
C13 C 0.3156(3) 0.3925(6) 0.46519(11) 0.0917(12) Uani 1 1 d . . . . .
H13 H 0.300537 0.247236 0.450896 0.110 Uiso 1 1 calc R U . . .
C14 C 0.2763(4) 0.4318(8) 0.50866(13) 0.1164(15) Uani 1 1 d . . . . .
H14 H 0.235182 0.312507 0.523618 0.140 Uiso 1 1 calc R U . . .
C15 C 0.2952(3) 0.6331(7) 0.52959(10) 0.0827(9) Uani 1 1 d . . . . .
H15 H 0.265543 0.661058 0.558797 0.099 Uiso 1 1 calc R U . . .
C16 C 0.3562(4) 0.7937(7) 0.50896(13) 0.1275(18) Uani 1 1 d . . . . .
H16 H 0.373430 0.935340 0.524233 0.153 Uiso 1 1 calc R U . . .
C17 C 0.3959(4) 0.7597(6) 0.46519(12) 0.1095(15) Uani 1 1 d . . . . .
H17 H 0.438031 0.879796 0.450932 0.131 Uiso 1 1 calc R U . . .
C18 C 0.30195(19) 0.5807(4) 0.34975(7) 0.0387(5) Uani 1 1 d . . . . .
C19 C 0.2428(2) 0.7874(4) 0.35510(9) 0.0539(6) Uani 1 1 d . . . . .
H19 H 0.264461 0.891757 0.378631 0.065 Uiso 1 1 calc R U . . .
C20 C 0.1526(2) 0.8438(5) 0.32658(10) 0.0589(7) Uani 1 1 d . . . . .
H20 H 0.112132 0.985450 0.330777 0.071 Uiso 1 1 calc R U . . .
C21 C 0.1215(2) 0.6949(5) 0.29219(9) 0.0593(7) Uani 1 1 d . . . . .
H21 H 0.059541 0.733472 0.272578 0.071 Uiso 1 1 calc R U . . .
C22 C 0.1800(3) 0.4909(5) 0.28625(10) 0.0667(8) Uani 1 1 d . . . . .
H22 H 0.158894 0.388622 0.262315 0.080 Uiso 1 1 calc R U . . .
C23 C 0.2697(2) 0.4328(5) 0.31489(8) 0.0536(6) Uani 1 1 d . . . . .
H23 H 0.309481 0.290353 0.310618 0.064 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 1.4820(17) . ?
P1 C11 1.812(3) . ?
P1 C12 1.807(2) . ?
P1 C18 1.803(2) . ?
O2 C8 1.203(3) . ?
O3 C7 1.457(3) . ?
O3 C8 1.344(3) . ?
C1 C2 1.377(4) . ?
C1 C6 1.377(4) . ?
C1 C7 1.490(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.368(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.359(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.359(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(5) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.490(4) . ?
C9 C10 1.319(4) . ?
C9 C11 1.508(3) . ?
C10 H10A 0.92(3) . ?
C10 H10B 1.04(4) . ?
C11 H11A 0.94(3) . ?
C11 H11B 0.93(3) . ?
C12 C13 1.358(4) . ?
C12 C17 1.351(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.327(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.321(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(3) . ?
C18 C23 1.384(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.374(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.369(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(4) . ?
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 C11 113.59(12) . . ?
O1 P1 C12 112.89(11) . . ?
O1 P1 C18 111.56(11) . . ?
C12 P1 C11 106.58(11) . . ?
C18 P1 C11 105.93(11) . . ?
C18 P1 C12 105.71(10) . . ?
C8 O3 C7 115.5(2) . . ?
C2 C1 C6 117.8(3) . . ?
C2 C1 C7 120.4(3) . . ?
C6 C1 C7 121.7(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O3 C7 C1 107.8(2) . . ?
O3 C7 H7A 110.1 . . ?
O3 C7 H7B 110.1 . . ?
C1 C7 H7A 110.1 . . ?
C1 C7 H7B 110.1 . . ?
H7A C7 H7B 108.5 . . ?
O2 C8 O3 123.4(2) . . ?
O2 C8 C9 124.8(3) . . ?
O3 C8 C9 111.7(2) . . ?
C8 C9 C11 120.4(2) . . ?
C10 C9 C8 118.4(3) . . ?
C10 C9 C11 121.2(3) . . ?
C9 C10 H10A 118(2) . . ?
C9 C10 H10B 120.7(19) . . ?
H10A C10 H10B 121(3) . . ?
P1 C11 H11A 105.0(14) . . ?
P1 C11 H11B 108.4(15) . . ?
C9 C11 P1 111.02(18) . . ?
C9 C11 H11A 112.0(14) . . ?
C9 C11 H11B 109.1(15) . . ?
H11A C11 H11B 111(2) . . ?
C13 C12 P1 117.7(2) . . ?
C17 C12 P1 125.6(2) . . ?
C17 C12 C13 116.8(3) . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.1(3) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.1(4) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.6(3) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.4(4) . . ?
C17 C16 H16 119.3 . . ?
C12 C17 C16 120.9(3) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 P1 123.36(19) . . ?
C19 C18 C23 118.6(2) . . ?
C23 C18 P1 118.08(18) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.5(2) . . ?
C22 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
P1 C12 C13 C14 -178.3(3) . . . . ?
P1 C12 C17 C16 178.8(4) . . . . ?
P1 C18 C19 C20 -179.2(2) . . . . ?
P1 C18 C23 C22 179.7(2) . . . . ?
O1 P1 C11 C9 63.4(2) . . . . ?
O1 P1 C12 C13 -34.6(3) . . . . ?
O1 P1 C12 C17 145.9(3) . . . . ?
O1 P1 C18 C19 166.62(19) . . . . ?
O1 P1 C18 C23 -13.3(2) . . . . ?
O2 C8 C9 C10 -27.7(4) . . . . ?
O2 C8 C9 C11 152.6(3) . . . . ?
O3 C8 C9 C10 149.7(3) . . . . ?
O3 C8 C9 C11 -30.0(3) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C2 C1 C7 O3 -69.2(4) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 C1 -0.4(5) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
C6 C1 C7 O3 111.5(3) . . . . ?
C7 O3 C8 O2 0.2(4) . . . . ?
C7 O3 C8 C9 -177.2(2) . . . . ?
C7 C1 C2 C3 -179.7(3) . . . . ?
C7 C1 C6 C5 179.8(3) . . . . ?
C8 O3 C7 C1 172.2(2) . . . . ?
C8 C9 C11 P1 -78.3(3) . . . . ?
C10 C9 C11 P1 101.9(3) . . . . ?
C11 P1 C12 C13 -160.0(3) . . . . ?
C11 P1 C12 C17 20.5(3) . . . . ?
C11 P1 C18 C19 -69.3(2) . . . . ?
C11 P1 C18 C23 110.7(2) . . . . ?
C12 P1 C11 C9 -171.69(17) . . . . ?
C12 P1 C18 C19 43.6(2) . . . . ?
C12 P1 C18 C23 -136.4(2) . . . . ?
C12 C13 C14 C15 0.4(7) . . . . ?
C13 C12 C17 C16 -0.6(6) . . . . ?
C13 C14 C15 C16 -2.5(7) . . . . ?
C14 C15 C16 C17 3.1(7) . . . . ?
C15 C16 C17 C12 -1.5(8) . . . . ?
C17 C12 C13 C14 1.2(6) . . . . ?
C18 P1 C11 C9 -59.4(2) . . . . ?
C18 P1 C12 C13 87.6(3) . . . . ?
C18 P1 C12 C17 -91.9(3) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
C19 C18 C23 C22 -0.2(4) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C20 C21 C22 C23 0.5(4) . . . . ?
C21 C22 C23 C18 -0.4(4) . . . . ?
C23 C18 C19 C20 0.8(4) . . . . ?

_olex2_date_sample_data_collection 2023-06-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.796
####################################################################### 
# 
# 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_1-77
_database_code_depnum_ccdc_archive 'CCDC 2372954'
loop_
_audit_author_name
_audit_author_address
'Wei Ding'
;Zhengzhou University
China
;
_audit_update_record             
;
2024-07-23 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_audit_creation_date             2023-07-24
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H30 O2 P2'
_chemical_formula_sum            'C30 H30 O2 P2'
_chemical_formula_weight         484.48
_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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.6884(2)
_cell_length_b                   11.3043(2)
_cell_length_c                   35.0872(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5032.68(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6706
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.4140
_cell_measurement_theta_min      4.2620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.762
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_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       42
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            12078
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.583
_diffrn_reflns_theta_min         2.519
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00   0.00   1.00    1.00    --  -40.73 -19.00  30.00   60
  2  ω     24.00  52.00   1.00    1.00    --   40.73-125.00   0.00   28
  3  ω     34.00  87.00   1.00    1.00    --   40.73-125.00 120.00   53
  4  ω     58.00 128.00   1.00    1.47    --  106.95 -45.00  30.00   70
  5  ω    136.00 167.00   1.00    1.47    --  106.95  45.00 -90.00   31
  6  ω     98.00 173.00   1.00    1.47    --  106.95  61.00  60.00   75
  7  ω     84.00 166.00   1.00    1.47    --  106.95  61.00-180.00   82
  8  ω   -118.00 -72.00   1.00    1.00    --  -40.73 -19.00  30.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0738576000
_diffrn_orient_matrix_UB_12      0.0206588000
_diffrn_orient_matrix_UB_13      -0.0342194000
_diffrn_orient_matrix_UB_21      -0.0450338000
_diffrn_orient_matrix_UB_22      -0.1108828000
_diffrn_orient_matrix_UB_23      -0.0196629000
_diffrn_orient_matrix_UB_31      -0.0851707000
_diffrn_orient_matrix_UB_32      0.0764902000
_diffrn_orient_matrix_UB_33      -0.0192652000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4534
_reflns_number_total             4969
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.00053(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4969
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0748P)²+1.7158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1264
_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.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.23387(3) 0.48893(4) 0.61646(2) 0.01899(14) Uani 1 1 d . . . . .
P2 P 0.57485(3) 0.56355(4) 0.66871(2) 0.01947(14) Uani 1 1 d . . . . .
O1 O 0.26769(10) 0.36296(12) 0.61782(4) 0.0274(3) Uani 1 1 d . . . . .
O2 O 0.50952(10) 0.65759(11) 0.68635(4) 0.0256(3) Uani 1 1 d . . . . .
C1 C 0.18385(13) 0.52842(17) 0.56974(5) 0.0235(4) Uani 1 1 d . . . . .
C2 C 0.13167(15) 0.63496(19) 0.56324(5) 0.0304(4) Uani 1 1 d . . . . .
H2 H 0.118950 0.687884 0.583760 0.036 Uiso 1 1 calc R U . . .
C3 C 0.09828(18) 0.6636(2) 0.52671(6) 0.0410(5) Uani 1 1 d . . . . .
H3 H 0.062873 0.736366 0.522205 0.049 Uiso 1 1 calc R U . . .
C4 C 0.11657(18) 0.5863(3) 0.49686(6) 0.0455(6) Uani 1 1 d . . . . .
H4 H 0.092661 0.605694 0.471967 0.055 Uiso 1 1 calc R U . . .
C5 C 0.16919(18) 0.4816(2) 0.50300(6) 0.0436(6) Uani 1 1 d . . . . .
H5 H 0.182279 0.429260 0.482347 0.052 Uiso 1 1 calc R U . . .
C6 C 0.20318(16) 0.4524(2) 0.53950(6) 0.0318(4) Uani 1 1 d . . . . .
H6 H 0.239722 0.380215 0.543736 0.038 Uiso 1 1 calc R U . . .
C7 C 0.13087(13) 0.52102(16) 0.65035(5) 0.0205(4) Uani 1 1 d . . . . .
C8 C 0.11198(14) 0.63489(17) 0.66415(5) 0.0242(4) Uani 1 1 d . . . . .
H8 H 0.152969 0.699747 0.655383 0.029 Uiso 1 1 calc R U . . .
C9 C 0.03259(15) 0.65236(18) 0.69083(5) 0.0291(4) Uani 1 1 d . . . . .
H9 H 0.019215 0.729631 0.700313 0.035 Uiso 1 1 calc R U . . .
C10 C -0.02718(15) 0.55803(19) 0.70372(5) 0.0308(4) Uani 1 1 d . . . . .
H10 H -0.082171 0.571156 0.721598 0.037 Uiso 1 1 calc R U . . .
C11 C -0.00722(15) 0.44477(18) 0.69067(5) 0.0291(4) Uani 1 1 d . . . . .
H11 H -0.047482 0.380045 0.699957 0.035 Uiso 1 1 calc R U . . .
C12 C 0.07179(14) 0.42586(17) 0.66398(5) 0.0242(4) Uani 1 1 d . . . . .
H12 H 0.085642 0.348122 0.654997 0.029 Uiso 1 1 calc R U . . .
C13 C 0.33890(13) 0.59434(15) 0.62582(5) 0.0198(3) Uani 1 1 d . . . . .
H13A H 0.320390 0.672185 0.614758 0.024 Uiso 1 1 calc R U . . .
H13B H 0.347956 0.604335 0.653654 0.024 Uiso 1 1 calc R U . . .
C14 C 0.44089(13) 0.54987(16) 0.60831(5) 0.0201(4) Uani 1 1 d . . . . .
C15 C 0.50186(13) 0.47053(16) 0.63535(5) 0.0208(4) Uani 1 1 d . . . . .
H15A H 0.551282 0.420008 0.620798 0.025 Uiso 1 1 calc R U . . .
H15B H 0.452631 0.418548 0.649444 0.025 Uiso 1 1 calc R U . . .
C16 C 0.47338(14) 0.57852(16) 0.57323(5) 0.0233(4) Uani 1 1 d . . . . .
C17 C 0.57152(15) 0.5300(2) 0.55491(6) 0.0333(5) Uani 1 1 d . . . . .
H17A H 0.609439 0.480510 0.573287 0.050 Uiso 1 1 calc R U . . .
H17B H 0.616869 0.595599 0.546863 0.050 Uiso 1 1 calc R U . . .
H17C H 0.552174 0.482359 0.532654 0.050 Uiso 1 1 calc R U . . .
C18 C 0.41581(16) 0.66485(19) 0.54813(6) 0.0328(5) Uani 1 1 d . . . . .
H18A H 0.388511 0.623506 0.525655 0.049 Uiso 1 1 calc R U . . .
H18B H 0.464314 0.727471 0.540040 0.049 Uiso 1 1 calc R U . . .
H18C H 0.357086 0.699851 0.562345 0.049 Uiso 1 1 calc R U . . .
C19 C 0.68054(14) 0.62404(16) 0.63951(5) 0.0226(4) Uani 1 1 d . . . . .
C20 C 0.77620(14) 0.56627(18) 0.63442(5) 0.0264(4) Uani 1 1 d . . . . .
H20 H 0.790476 0.495537 0.648102 0.032 Uiso 1 1 calc R U . . .
C21 C 0.85123(15) 0.61146(19) 0.60939(6) 0.0319(4) Uani 1 1 d . . . . .
H21 H 0.916657 0.571892 0.606103 0.038 Uiso 1 1 calc R U . . .
C22 C 0.83023(16) 0.71428(19) 0.58928(5) 0.0327(4) Uani 1 1 d . . . . .
H22 H 0.880445 0.744139 0.571656 0.039 Uiso 1 1 calc R U . . .
C23 C 0.73603(16) 0.77341(19) 0.59490(6) 0.0321(4) Uani 1 1 d . . . . .
H23 H 0.722432 0.844743 0.581460 0.039 Uiso 1 1 calc R U . . .
C24 C 0.66125(15) 0.72931(17) 0.62003(5) 0.0266(4) Uani 1 1 d . . . . .
H24 H 0.597042 0.770792 0.623956 0.032 Uiso 1 1 calc R U . . .
C25 C 0.63518(13) 0.46819(16) 0.70362(5) 0.0209(4) Uani 1 1 d . . . . .
C26 C 0.64018(15) 0.50865(17) 0.74109(5) 0.0263(4) Uani 1 1 d . . . . .
H26 H 0.608414 0.581847 0.747792 0.032 Uiso 1 1 calc R U . . .
C27 C 0.69148(17) 0.44208(19) 0.76855(5) 0.0335(5) Uani 1 1 d . . . . .
H27 H 0.695138 0.470259 0.794022 0.040 Uiso 1 1 calc R U . . .
C28 C 0.73732(16) 0.33519(19) 0.75925(6) 0.0327(5) Uani 1 1 d . . . . .
H28 H 0.774075 0.291191 0.778106 0.039 Uiso 1 1 calc R U . . .
C29 C 0.72966(15) 0.29209(19) 0.72233(6) 0.0290(4) Uani 1 1 d . . . . .
H29 H 0.759193 0.217373 0.716036 0.035 Uiso 1 1 calc R U . . .
C30 C 0.67877(14) 0.35839(17) 0.69466(5) 0.0252(4) Uani 1 1 d . . . . .
H30 H 0.673536 0.328818 0.669383 0.030 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 1.4880(14) . ?
P1 C1 1.8137(18) . ?
P1 C7 1.8037(18) . ?
P1 C13 1.8175(17) . ?
P2 O2 1.4833(13) . ?
P2 C15 1.8260(18) . ?
P2 C19 1.8210(18) . ?
P2 C25 1.8023(18) . ?
C1 C2 1.393(3) . ?
C1 C6 1.387(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(3) . ?
C7 C12 1.396(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.518(2) . ?
C14 C15 1.517(2) . ?
C14 C16 1.338(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.505(3) . ?
C16 C18 1.504(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.390(3) . ?
C19 C24 1.394(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.385(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.388(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.393(2) . ?
C25 C30 1.395(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.380(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.387(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.386(3) . ?
C30 H30 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C1 111.43(8) . . ?
O1 P1 C7 112.35(8) . . ?
O1 P1 C13 114.22(8) . . ?
C1 P1 C13 104.98(8) . . ?
C7 P1 C1 107.02(8) . . ?
C7 P1 C13 106.29(8) . . ?
O2 P2 C15 113.37(8) . . ?
O2 P2 C19 112.16(8) . . ?
O2 P2 C25 112.49(8) . . ?
C19 P2 C15 103.24(8) . . ?
C25 P2 C15 107.86(8) . . ?
C25 P2 C19 107.11(8) . . ?
C2 C1 P1 121.82(14) . . ?
C6 C1 P1 118.48(15) . . ?
C6 C1 C2 119.62(18) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.2(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 P1 122.58(14) . . ?
C12 C7 P1 117.39(14) . . ?
C12 C7 C8 119.98(17) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.29(17) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.52(18) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.31(18) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.87(18) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.02(18) . . ?
C11 C12 H12 120.0 . . ?
P1 C13 H13A 109.8 . . ?
P1 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 P1 109.57(12) . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
C15 C14 C13 112.17(15) . . ?
C16 C14 C13 123.69(16) . . ?
C16 C14 C15 124.14(16) . . ?
P2 C15 H15A 110.0 . . ?
P2 C15 H15B 110.0 . . ?
C14 C15 P2 108.61(12) . . ?
C14 C15 H15A 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.3 . . ?
C14 C16 C17 124.04(17) . . ?
C14 C16 C18 123.10(17) . . ?
C18 C16 C17 112.85(16) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 P2 122.61(14) . . ?
C20 C19 C24 119.45(17) . . ?
C24 C19 P2 117.85(14) . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.38(19) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.83(19) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 119.93(18) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.50(19) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 H24 120.1 . . ?
C23 C24 C19 119.87(18) . . ?
C23 C24 H24 120.1 . . ?
C26 C25 P2 117.66(14) . . ?
C26 C25 C30 119.14(17) . . ?
C30 C25 P2 123.18(13) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 119.96(18) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.62(18) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 119.91(18) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.79(19) . . ?
C30 C29 H29 120.1 . . ?
C25 C30 H30 119.7 . . ?
C29 C30 C25 120.52(17) . . ?
C29 C30 H30 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 177.50(16) . . . . ?
P1 C1 C6 C5 -177.82(16) . . . . ?
P1 C7 C8 C9 -178.66(14) . . . . ?
P1 C7 C12 C11 178.76(14) . . . . ?
P1 C13 C14 C15 -88.21(15) . . . . ?
P1 C13 C14 C16 92.39(19) . . . . ?
P2 C19 C20 C21 174.81(14) . . . . ?
P2 C19 C24 C23 -174.49(15) . . . . ?
P2 C25 C26 C27 -176.02(15) . . . . ?
P2 C25 C30 C29 176.15(14) . . . . ?
O1 P1 C1 C2 169.18(15) . . . . ?
O1 P1 C1 C6 -14.07(17) . . . . ?
O1 P1 C7 C8 156.76(14) . . . . ?
O1 P1 C7 C12 -20.60(16) . . . . ?
O1 P1 C13 C14 36.90(15) . . . . ?
O2 P2 C15 C14 48.69(14) . . . . ?
O2 P2 C19 C20 149.93(14) . . . . ?
O2 P2 C19 C24 -33.65(16) . . . . ?
O2 P2 C25 C26 -17.39(17) . . . . ?
O2 P2 C25 C30 164.22(14) . . . . ?
C1 P1 C7 C8 -80.62(16) . . . . ?
C1 P1 C7 C12 102.02(14) . . . . ?
C1 P1 C13 C14 -85.44(13) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C7 P1 C1 C2 45.99(17) . . . . ?
C7 P1 C1 C6 -137.26(15) . . . . ?
C7 P1 C13 C14 161.37(12) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C7 C12 C11 1.3(3) . . . . ?
C8 C9 C10 C11 1.2(3) . . . . ?
C9 C10 C11 C12 -1.2(3) . . . . ?
C10 C11 C12 C7 0.0(3) . . . . ?
C12 C7 C8 C9 -1.4(3) . . . . ?
C13 P1 C1 C2 -66.69(17) . . . . ?
C13 P1 C1 C6 110.07(15) . . . . ?
C13 P1 C7 C8 31.15(16) . . . . ?
C13 P1 C7 C12 -146.20(13) . . . . ?
C13 C14 C15 P2 -80.95(15) . . . . ?
C13 C14 C16 C17 -176.77(17) . . . . ?
C13 C14 C16 C18 4.3(3) . . . . ?
C15 P2 C19 C20 -87.67(16) . . . . ?
C15 P2 C19 C24 88.75(15) . . . . ?
C15 P2 C25 C26 -143.16(14) . . . . ?
C15 P2 C25 C30 38.45(17) . . . . ?
C15 C14 C16 C17 3.9(3) . . . . ?
C15 C14 C16 C18 -175.04(17) . . . . ?
C16 C14 C15 P2 98.45(18) . . . . ?
C19 P2 C15 C14 -72.89(13) . . . . ?
C19 P2 C25 C26 106.30(15) . . . . ?
C19 P2 C25 C30 -72.10(16) . . . . ?
C19 C20 C21 C22 -0.3(3) . . . . ?
C20 C19 C24 C23 2.0(3) . . . . ?
C20 C21 C22 C23 1.7(3) . . . . ?
C21 C22 C23 C24 -1.3(3) . . . . ?
C22 C23 C24 C19 -0.6(3) . . . . ?
C24 C19 C20 C21 -1.6(3) . . . . ?
C25 P2 C15 C14 173.94(11) . . . . ?
C25 P2 C19 C20 26.04(17) . . . . ?
C25 P2 C19 C24 -157.53(14) . . . . ?
C25 C26 C27 C28 -0.5(3) . . . . ?
C26 C25 C30 C29 -2.2(3) . . . . ?
C26 C27 C28 C29 -1.8(3) . . . . ?
C27 C28 C29 C30 2.0(3) . . . . ?
C28 C29 C30 C25 0.0(3) . . . . ?
C30 C25 C26 C27 2.4(3) . . . . ?

_olex2_date_sample_data_collection 2023-07-24
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.614
_oxdiff_exptl_absorpt_empirical_full_min 0.715
