# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_exp_6288
_database_code_depnum_ccdc_archive 'CCDC 2212080'
loop_
_audit_author_name
_audit_author_address
'Jian Hao'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2022-10-10 deposited with the CCDC.	2022-12-22 downloaded from the CCDC.
;
_audit_creation_date             2019-12-17
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            
'dibenzo[b,f]benzo[4,5][1,2]aza-phosphinino[1,6-d][1,4]oxazepine 15-oxide'
_chemical_name_systematic        
;
 rel-(4bR,15R)-15-Ethoxy-3-(trifluoromethyl)-4b,16-dihydrodibenzo[b,f]benzo[4,5][1,2]aza-phosphinino[1,6-d][1,4]oxazepine 15-oxide 
;
_chemical_formula_moiety         'C23 H19 F3 N O3 P'
_chemical_formula_sum            'C23 H19 F3 N O3 P'
_chemical_formula_weight         445.36
_chemical_melting_point          '167-169 deg'
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'
F F 0.0171 0.0103 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.2468(5)
_cell_length_b                   10.0570(5)
_cell_length_c                   16.8219(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.021(4)
_cell_angle_gamma                90.00
_cell_volume                     2026.46(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3130
_cell_measurement_temperature    112.35(10)
_cell_measurement_theta_max      28.6920
_cell_measurement_theta_min      3.7470
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8380
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.07
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      112.35(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.8380
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   58.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   57.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega   27.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   57.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega   49.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  178.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega   43.00   78.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  178.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  5 omega   31.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   19.0000  150.0000 59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0424285000
_diffrn_orient_matrix_UB_12      0.0216527000
_diffrn_orient_matrix_UB_13      0.0200266000
_diffrn_orient_matrix_UB_21      -0.0399223000
_diffrn_orient_matrix_UB_22      -0.0378313000
_diffrn_orient_matrix_UB_23      -0.0274730000
_diffrn_orient_matrix_UB_31      0.0106707000
_diffrn_orient_matrix_UB_32      -0.0554352000
_diffrn_orient_matrix_UB_33      0.0265391000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3300
_reflns_number_total             3971
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3971
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0340P)²+1.2050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0981
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
P1 P 0.47307(4) 0.60856(5) 0.18296(3) 0.01679(14) Uani 1 1 d . . .
F1 F 0.8019(7) 0.8486(4) -0.1097(3) 0.0668(17) Uani 0.574(10) 1 d PDU A 2
F2 F 0.6900(3) 0.9863(4) -0.0753(3) 0.0448(10) Uani 0.574(10) 1 d PDU A 2
F3 F 0.8527(7) 0.9724(10) -0.0043(5) 0.062(2) Uani 0.574(10) 1 d PDU A 2
F4 F 0.8679(7) 0.8312(5) -0.0681(6) 0.064(2) Uani 0.426(10) 1 d PDU A 1
F5 F 0.7129(6) 0.9293(12) -0.1058(4) 0.084(3) Uani 0.426(10) 1 d PDU A 1
F6 F 0.8310(9) 0.9907(11) -0.0002(7) 0.0428(17) Uani 0.426(10) 1 d PDU A 1
O1 O 0.43144(11) 0.52251(15) 0.24935(8) 0.0214(3) Uani 1 1 d . . .
O2 O 0.37686(11) 0.64043(15) 0.11795(8) 0.0229(3) Uani 1 1 d . . .
O3 O 0.66149(12) 0.81918(19) 0.39341(8) 0.0358(4) Uani 1 1 d . . .
N1 N 0.54515(13) 0.73454(17) 0.23193(9) 0.0158(4) Uani 1 1 d . . .
C1 C 0.58321(17) 0.5204(2) 0.15012(12) 0.0197(4) Uani 1 1 d . . .
H1A H 0.6387 0.4888 0.1978 0.024 Uiso 1 1 calc R . .
H1B H 0.5525 0.4421 0.1172 0.024 Uiso 1 1 calc R . .
C2 C 0.63826(16) 0.6135(2) 0.09983(11) 0.0176(4) Uani 1 1 d . . .
C3 C 0.65568(16) 0.5778(2) 0.02340(11) 0.0218(5) Uani 1 1 d . . .
H3 H 0.6353 0.4914 0.0027 0.026 Uiso 1 1 calc R . .
C4 C 0.70228(17) 0.6667(2) -0.02254(12) 0.0239(5) Uani 1 1 d . . .
H4 H 0.7148 0.6413 -0.0743 0.029 Uiso 1 1 calc R . .
C5 C 0.73084(17) 0.7938(2) 0.00744(12) 0.0223(5) Uani 1 1 d . A .
C6 C 0.71348(16) 0.8313(2) 0.08389(11) 0.0193(4) Uani 1 1 d . . .
H6 H 0.7325 0.9185 0.1039 0.023 Uiso 1 1 calc R . .
C7 C 0.66833(15) 0.7409(2) 0.13055(11) 0.0165(4) Uani 1 1 d . . .
C8 C 0.77605(19) 0.8930(3) -0.04350(12) 0.0322(5) Uani 1 1 d DU . .
C9 C 0.65411(15) 0.7798(2) 0.21492(11) 0.0161(4) Uani 1 1 d . . .
H9 H 0.6538 0.8792 0.2168 0.019 Uiso 1 1 calc R . .
C10 C 0.74913(16) 0.73342(19) 0.28298(11) 0.0159(4) Uani 1 1 d . . .
C11 C 0.74397(16) 0.7543(2) 0.36450(11) 0.0187(4) Uani 1 1 d . . .
C12 C 0.83112(17) 0.7139(2) 0.42727(12) 0.0212(4) Uani 1 1 d . . .
H12 H 0.8259 0.7276 0.4822 0.025 Uiso 1 1 calc R . .
C13 C 0.92498(17) 0.6540(2) 0.40966(12) 0.0230(5) Uani 1 1 d . . .
H13 H 0.9840 0.6263 0.4525 0.028 Uiso 1 1 calc R . .
C14 C 0.93305(17) 0.6344(2) 0.32932(13) 0.0241(5) Uani 1 1 d . . .
H14 H 0.9980 0.5951 0.3169 0.029 Uiso 1 1 calc R . .
C15 C 0.84505(16) 0.6728(2) 0.26729(12) 0.0207(4) Uani 1 1 d . . .
H15 H 0.8503 0.6574 0.2125 0.025 Uiso 1 1 calc R . .
C16 C 0.55896(16) 0.8686(2) 0.35426(11) 0.0194(4) Uani 1 1 d . . .
C17 C 0.49672(16) 0.8244(2) 0.28006(11) 0.0158(4) Uani 1 1 d . . .
C18 C 0.38904(16) 0.8750(2) 0.25334(12) 0.0207(4) Uani 1 1 d . . .
H18 H 0.3457 0.8461 0.2027 0.025 Uiso 1 1 calc R . .
C19 C 0.34450(18) 0.9662(2) 0.29923(12) 0.0243(5) Uani 1 1 d . . .
H19 H 0.2703 0.9973 0.2810 0.029 Uiso 1 1 calc R . .
C20 C 0.40858(18) 1.0122(2) 0.37196(12) 0.0234(5) Uani 1 1 d . . .
H20 H 0.3789 1.0764 0.4031 0.028 Uiso 1 1 calc R . .
C21 C 0.51576(18) 0.9641(2) 0.39892(12) 0.0237(5) Uani 1 1 d . . .
H21 H 0.5601 0.9966 0.4482 0.028 Uiso 1 1 calc R . .
C22 C 0.50291(18) 0.4799(2) 0.32525(12) 0.0260(5) Uani 1 1 d . . .
H22A H 0.5064 0.5497 0.3672 0.031 Uiso 1 1 calc R . .
H22B H 0.5795 0.4629 0.3173 0.031 Uiso 1 1 calc R . .
C23 C 0.4535(2) 0.3546(2) 0.35145(13) 0.0324(6) Uani 1 1 d . . .
H23A H 0.3780 0.3728 0.3596 0.049 Uiso 1 1 calc R . .
H23B H 0.5002 0.3228 0.4025 0.049 Uiso 1 1 calc R . .
H23C H 0.4502 0.2865 0.3094 0.049 Uiso 1 1 calc R . .


_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 1.5790(14) . ?
P1 O2 1.4664(14) . ?
P1 N1 1.6614(16) . ?
P1 C1 1.795(2) . ?
F1 C8 1.299(4) . ?
F2 C8 1.428(4) . ?
F3 C8 1.302(7) . ?
F4 C8 1.420(5) . ?
F5 C8 1.222(5) . ?
F6 C8 1.321(8) . ?
O1 C22 1.454(2) . ?
O3 C11 1.374(2) . ?
O3 C16 1.383(2) . ?
N1 C9 1.493(2) . ?
N1 C17 1.423(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.511(3) . ?
C2 C3 1.394(3) . ?
C2 C7 1.402(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
C5 C6 1.398(3) . ?
C5 C8 1.495(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(3) . ?
C7 C9 1.517(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.526(3) . ?
C10 C11 1.402(3) . ?
C10 C15 1.397(3) . ?
C11 C12 1.396(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(3) . ?
C16 C21 1.390(3) . ?
C17 C18 1.397(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(3) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.503(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 N1 106.48(8) . . ?
O1 P1 C1 108.72(9) . . ?
O2 P1 O1 108.64(8) . . ?
O2 P1 N1 117.68(9) . . ?
O2 P1 C1 114.65(9) . . ?
N1 P1 C1 100.00(9) . . ?
C22 O1 P1 123.96(12) . . ?
C11 O3 C16 131.57(15) . . ?
C9 N1 P1 122.77(12) . . ?
C17 N1 P1 121.67(13) . . ?
C17 N1 C9 114.26(15) . . ?
P1 C1 H1A 110.0 . . ?
P1 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C2 C1 P1 108.51(14) . . ?
C2 C1 H1A 110.0 . . ?
C2 C1 H1B 110.0 . . ?
C3 C2 C1 121.90(19) . . ?
C3 C2 C7 119.78(19) . . ?
C7 C2 C1 118.27(16) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.61(18) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.43(19) . . ?
C4 C5 C8 120.04(18) . . ?
C6 C5 C8 119.5(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.83(19) . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C9 120.52(18) . . ?
C6 C7 C2 119.67(17) . . ?
C6 C7 C9 119.80(18) . . ?
F1 C8 F2 101.4(3) . . ?
F1 C8 F3 111.6(5) . . ?
F1 C8 F4 41.4(2) . . ?
F1 C8 F6 122.8(6) . . ?
F1 C8 C5 116.6(3) . . ?
F2 C8 C5 108.7(2) . . ?
F3 C8 F2 100.7(5) . . ?
F3 C8 F4 83.4(5) . . ?
F3 C8 F6 15.0(8) . . ?
F3 C8 C5 115.6(5) . . ?
F4 C8 F2 138.2(3) . . ?
F4 C8 C5 106.6(3) . . ?
F5 C8 F1 65.8(4) . . ?
F5 C8 F2 36.6(5) . . ?
F5 C8 F3 120.9(7) . . ?
F5 C8 F4 106.2(4) . . ?
F5 C8 F6 114.2(7) . . ?
F5 C8 C5 116.6(3) . . ?
F6 C8 F2 88.3(6) . . ?
F6 C8 F4 98.2(5) . . ?
F6 C8 C5 112.8(6) . . ?
N1 C9 C7 112.48(15) . . ?
N1 C9 H9 106.8 . . ?
N1 C9 C10 109.61(15) . . ?
C7 C9 H9 106.8 . . ?
C7 C9 C10 113.91(16) . . ?
C10 C9 H9 106.8 . . ?
C11 C10 C9 120.38(17) . . ?
C15 C10 C9 122.12(17) . . ?
C15 C10 C11 117.47(17) . . ?
O3 C11 C10 127.14(17) . . ?
O3 C11 C12 111.91(17) . . ?
C12 C11 C10 120.87(19) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.21(18) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.05(18) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.31(19) . . ?
C15 C14 H14 120.3 . . ?
C10 C15 H15 119.0 . . ?
C14 C15 C10 122.06(18) . . ?
C14 C15 H15 119.0 . . ?
O3 C16 C17 125.81(18) . . ?
O3 C16 C21 113.63(17) . . ?
C21 C16 C17 120.40(18) . . ?
C16 C17 N1 119.84(17) . . ?
C16 C17 C18 118.40(18) . . ?
C18 C17 N1 121.70(17) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.18(18) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.80(19) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.76(19) . . ?
C21 C20 H20 120.1 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.39(19) . . ?
C20 C21 H21 119.8 . . ?
O1 C22 H22A 110.2 . . ?
O1 C22 H22B 110.2 . . ?
O1 C22 C23 107.42(17) . . ?
H22A C22 H22B 108.5 . . ?
C23 C22 H22A 110.2 . . ?
C23 C22 H22B 110.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O1 C22 C23 -153.57(15) . . . . ?
P1 N1 C9 C7 23.1(2) . . . . ?
P1 N1 C9 C10 -104.70(16) . . . . ?
P1 N1 C17 C16 139.53(16) . . . . ?
P1 N1 C17 C18 -43.4(2) . . . . ?
P1 C1 C2 C3 -129.57(17) . . . . ?
P1 C1 C2 C7 48.0(2) . . . . ?
O1 P1 N1 C9 136.23(14) . . . . ?
O1 P1 N1 C17 -57.56(16) . . . . ?
O1 P1 C1 C2 -168.75(12) . . . . ?
O2 P1 O1 C22 -175.92(16) . . . . ?
O2 P1 N1 C9 -101.66(15) . . . . ?
O2 P1 N1 C17 64.56(17) . . . . ?
O2 P1 C1 C2 69.46(15) . . . . ?
O3 C11 C12 C13 -176.07(19) . . . . ?
O3 C16 C17 N1 -9.9(3) . . . . ?
O3 C16 C17 C18 173.0(2) . . . . ?
O3 C16 C21 C20 -172.82(19) . . . . ?
N1 P1 O1 C22 -48.25(17) . . . . ?
N1 P1 C1 C2 -57.41(14) . . . . ?
N1 C9 C10 C11 -48.7(2) . . . . ?
N1 C9 C10 C15 133.14(19) . . . . ?
N1 C17 C18 C19 -177.44(18) . . . . ?
C1 P1 O1 C22 58.69(18) . . . . ?
C1 P1 N1 C9 23.15(16) . . . . ?
C1 P1 N1 C17 -170.63(15) . . . . ?
C1 C2 C3 C4 177.49(18) . . . . ?
C1 C2 C7 C6 -176.51(17) . . . . ?
C1 C2 C7 C9 4.7(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C2 C7 C9 N1 -43.4(2) . . . . ?
C2 C7 C9 C10 82.1(2) . . . . ?
C3 C2 C7 C6 1.1(3) . . . . ?
C3 C2 C7 C9 -177.65(17) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C8 -176.95(19) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C4 C5 C8 F1 -9.8(5) . . . . ?
C4 C5 C8 F2 103.9(3) . . . . ?
C4 C5 C8 F3 -143.9(5) . . . . ?
C4 C5 C8 F4 -53.3(5) . . . . ?
C4 C5 C8 F5 65.0(8) . . . . ?
C4 C5 C8 F6 -160.0(6) . . . . ?
C5 C6 C7 C2 -1.4(3) . . . . ?
C5 C6 C7 C9 177.40(18) . . . . ?
C6 C5 C8 F1 172.7(5) . . . . ?
C6 C5 C8 F2 -73.6(3) . . . . ?
C6 C5 C8 F3 38.6(6) . . . . ?
C6 C5 C8 F4 129.2(5) . . . . ?
C6 C5 C8 F5 -112.5(8) . . . . ?
C6 C5 C8 F6 22.5(6) . . . . ?
C6 C7 C9 N1 137.88(18) . . . . ?
C6 C7 C9 C10 -96.6(2) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C7 C9 C10 C11 -175.75(18) . . . . ?
C7 C9 C10 C15 6.1(3) . . . . ?
C8 C5 C6 C7 178.05(19) . . . . ?
C9 N1 C17 C16 -53.2(2) . . . . ?
C9 N1 C17 C18 123.91(19) . . . . ?
C9 C10 C11 O3 -2.7(3) . . . . ?
C9 C10 C11 C12 -179.12(18) . . . . ?
C9 C10 C15 C14 177.96(19) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 O3 C16 C17 24.6(4) . . . . ?
C11 O3 C16 C21 -160.0(2) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C13 C14 C15 C10 1.4(3) . . . . ?
C15 C10 C11 O3 175.5(2) . . . . ?
C15 C10 C11 C12 -0.9(3) . . . . ?
C16 O3 C11 C10 7.4(4) . . . . ?
C16 O3 C11 C12 -175.8(2) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C17 N1 C9 C7 -144.04(16) . . . . ?
C17 N1 C9 C10 88.15(19) . . . . ?
C17 C16 C21 C20 2.8(3) . . . . ?
C17 C18 C19 C20 2.1(3) . . . . ?
C18 C19 C20 C21 -1.4(3) . . . . ?
C19 C20 C21 C16 -1.0(3) . . . . ?
C21 C16 C17 N1 175.03(18) . . . . ?
C21 C16 C17 C18 -2.1(3) . . . . ?
