# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_230629zh_zhcz255386_0m
_database_code_depnum_ccdc_archive 'CCDC 2307140'
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-07-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H31 N2 O3 P'
_chemical_formula_sum            'C33 H31 N2 O3 P'
_chemical_formula_weight         534.57
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2543 0.3332 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.7228(3)
_cell_length_b                   15.2917(5)
_cell_length_c                   19.0023(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2825.23(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      59.58
_cell_measurement_theta_min      3.23
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1227 before and 0.0658 after correction.
The Ratio of minimum to maximum transmission is 0.9021.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.13
_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  0.0399
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            41702
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.290
_diffrn_reflns_theta_min         3.227
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   MetalJet
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                5790
_reflns_number_total             6329
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.10-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 2388 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.034
_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)+(0.0401P)²+0.4138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C18(H18), C17(H17), C2(H2), C26(H26), C3(H3), C21(H21), C20(H20),
 C5(H5), C33(H33), C4(H4), C32(H32), C10(H10), C27(H27), C31(H31), C28(H28),
 C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C14(H14A,H14B,H14C)
;
_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 0.41639(5) 0.52611(3) 0.63643(3) 0.02739(11) Uani 1 1 d . . . . .
O2 O 0.43842(14) 0.61583(8) 0.77254(7) 0.0321(3) Uani 1 1 d . . . . .
O1 O 0.43160(15) 0.48336(10) 0.56736(7) 0.0386(3) Uani 1 1 d . . . . .
N1 N 0.34167(16) 0.62338(10) 0.63153(8) 0.0307(3) Uani 1 1 d . . . . .
H1 H 0.374365 0.663080 0.660583 0.037 Uiso 1 1 calc R U . . .
O3 O 0.44781(19) 0.53233(11) 0.87016(9) 0.0563(4) Uani 1 1 d . . . . .
N2 N 0.27589(19) 0.79137(11) 0.63933(9) 0.0363(4) Uani 1 1 d . . . . .
C9 C 0.5689(2) 0.58963(11) 0.74905(11) 0.0320(4) Uani 1 1 d . . . . .
C18 C 0.0845(2) 0.73919(13) 0.83510(10) 0.0349(4) Uani 1 1 d . . . . .
H18 H 0.050562 0.787149 0.808496 0.042 Uiso 1 1 calc R U . . .
C17 C 0.2058(2) 0.69956(12) 0.81505(11) 0.0328(4) Uani 1 1 d . . . . .
H17 H 0.254053 0.720130 0.774841 0.039 Uiso 1 1 calc R U . . .
C25 C 0.23457(19) 0.65172(13) 0.58818(10) 0.0296(4) Uani 1 1 d . . . . .
C1 C 0.31964(19) 0.45936(11) 0.69724(10) 0.0280(4) Uani 1 1 d . . . . .
C15 C 0.3886(2) 0.58602(13) 0.83596(11) 0.0357(5) Uani 1 1 d . . . . .
C30 C 0.2019(2) 0.74243(13) 0.59314(10) 0.0304(4) Uani 1 1 d . . . . .
C16 C 0.2579(2) 0.62937(12) 0.85365(10) 0.0328(4) Uani 1 1 d . . . . .
C2 C 0.1938(2) 0.48869(13) 0.72282(10) 0.0337(4) Uani 1 1 d . . . . .
H2 H 0.158659 0.543442 0.707486 0.040 Uiso 1 1 calc R U . . .
C8 C 0.5757(2) 0.55273(12) 0.68183(10) 0.0309(4) Uani 1 1 d . . . . .
C6 C 0.3708(2) 0.37799(13) 0.71943(12) 0.0361(4) Uani 1 1 d . . . . .
C26 C 0.1643(2) 0.59972(15) 0.54172(12) 0.0421(5) Uani 1 1 d . . . . .
H26 H 0.185766 0.539253 0.538288 0.050 Uiso 1 1 calc R U . . .
C22 C -0.1210(2) 0.75751(15) 0.91371(12) 0.0408(5) Uani 1 1 d . . . . .
H22 H -0.176763 0.763713 0.869764 0.049 Uiso 1 1 calc R U . . .
C3 C 0.1191(2) 0.43926(15) 0.77026(13) 0.0439(5) Uani 1 1 d . . . . .
H3 H 0.032099 0.459206 0.786355 0.053 Uiso 1 1 calc R U . . .
C21 C 0.1831(3) 0.59909(14) 0.91128(10) 0.0391(5) Uani 1 1 d . . . . .
H21 H 0.216147 0.550438 0.937370 0.047 Uiso 1 1 calc R U . . .
C20 C 0.0619(3) 0.63880(13) 0.93087(10) 0.0388(5) Uani 1 1 d . . . . .
H20 H 0.012537 0.617104 0.970318 0.047 Uiso 1 1 calc R U . . .
C19 C 0.0105(2) 0.71026(13) 0.89380(10) 0.0338(4) Uani 1 1 d . . . . .
C5 C 0.2951(3) 0.33111(14) 0.76897(13) 0.0463(6) Uani 1 1 d . . . . .
H5 H 0.330095 0.277013 0.785835 0.056 Uiso 1 1 calc R U . . .
C29 C 0.0987(2) 0.77764(15) 0.54949(12) 0.0414(5) Uani 1 1 d . . . . .
C33 C 0.0744(3) 0.86895(16) 0.55507(13) 0.0527(6) Uani 1 1 d . . . . .
H33 H 0.004924 0.895872 0.527405 0.063 Uiso 1 1 calc R U . . .
C4 C 0.1713(3) 0.36106(15) 0.79406(13) 0.0515(6) Uani 1 1 d . . . . .
H4 H 0.121805 0.327804 0.827835 0.062 Uiso 1 1 calc R U . . .
C32 C 0.1505(3) 0.91714(16) 0.59981(14) 0.0522(7) Uani 1 1 d . . . . .
H32 H 0.136544 0.978492 0.603130 0.063 Uiso 1 1 calc R U . . .
C10 C 0.6829(2) 0.60907(14) 0.78897(14) 0.0458(6) Uani 1 1 d . . . . .
H10 H 0.673885 0.632826 0.834930 0.055 Uiso 1 1 calc R U . . .
C27 C 0.0603(3) 0.63591(18) 0.49901(15) 0.0597(7) Uani 1 1 d . . . . .
H27 H 0.011460 0.599125 0.467391 0.072 Uiso 1 1 calc R U . . .
C7 C 0.5025(3) 0.33962(15) 0.69155(16) 0.0547(7) Uani 1 1 d . . . . .
H7A H 0.495946 0.333242 0.640344 0.082 Uiso 1 1 calc R U . . .
H7B H 0.517883 0.282164 0.712988 0.082 Uiso 1 1 calc R U . . .
H7C H 0.579359 0.378474 0.703163 0.082 Uiso 1 1 calc R U . . .
C31 C 0.2505(3) 0.87608(14) 0.64146(13) 0.0466(5) Uani 1 1 d . . . . .
H31 H 0.302750 0.911137 0.672898 0.056 Uiso 1 1 calc R U . . .
C28 C 0.0284(3) 0.72239(19) 0.50217(15) 0.0608(8) Uani 1 1 d . . . . .
H28 H -0.041307 0.745609 0.472505 0.073 Uiso 1 1 calc R U . . .
C11 C 0.8110(2) 0.59298(15) 0.76018(16) 0.0534(7) Uani 1 1 d . . . . .
H11 H 0.891623 0.606425 0.786305 0.064 Uiso 1 1 calc R U . . .
C12 C 0.8224(2) 0.55756(16) 0.69383(15) 0.0517(6) Uani 1 1 d . . . . .
H12 H 0.911417 0.547589 0.674843 0.062 Uiso 1 1 calc R U . . .
C13 C 0.7074(2) 0.53586(15) 0.65361(12) 0.0409(5) Uani 1 1 d . . . . .
C24 C -0.2100(3) 0.70935(18) 0.96699(15) 0.0586(7) Uani 1 1 d . . . . .
H24A H -0.225353 0.649245 0.950915 0.088 Uiso 1 1 calc R U . . .
H24B H -0.298548 0.739360 0.971679 0.088 Uiso 1 1 calc R U . . .
H24C H -0.163267 0.708422 1.012687 0.088 Uiso 1 1 calc R U . . .
C23 C -0.0899(3) 0.84930(15) 0.93989(14) 0.0525(6) Uani 1 1 d . . . . .
H23A H -0.039635 0.845879 0.984515 0.079 Uiso 1 1 calc R U . . .
H23B H -0.176245 0.881117 0.947061 0.079 Uiso 1 1 calc R U . . .
H23C H -0.033677 0.880090 0.904982 0.079 Uiso 1 1 calc R U . . .
C14 C 0.7325(3) 0.4945(2) 0.58247(14) 0.0634(8) Uani 1 1 d . . . . .
H14A H 0.721962 0.430972 0.586192 0.095 Uiso 1 1 calc R U . . .
H14B H 0.825891 0.508405 0.566648 0.095 Uiso 1 1 calc R U . . .
H14C H 0.665805 0.517463 0.548475 0.095 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 1.4737(14) . ?
P1 N1 1.6581(15) . ?
P1 C1 1.806(2) . ?
P1 C8 1.819(2) . ?
O2 C9 1.404(2) . ?
O2 C15 1.377(3) . ?
N1 H1 0.8800 . ?
N1 C25 1.397(2) . ?
O3 C15 1.195(3) . ?
N2 C30 1.360(3) . ?
N2 C31 1.319(3) . ?
C9 C8 1.398(3) . ?
C9 C10 1.375(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.380(3) . ?
C18 C19 1.399(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.395(3) . ?
C25 C30 1.426(3) . ?
C25 C26 1.370(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.405(3) . ?
C15 C16 1.472(3) . ?
C30 C29 1.409(3) . ?
C16 C21 1.394(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(3) . ?
C8 C13 1.412(3) . ?
C6 C5 1.393(3) . ?
C6 C7 1.504(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.410(3) . ?
C22 H22 1.0000 . ?
C22 C19 1.517(3) . ?
C22 C24 1.521(3) . ?
C22 C23 1.520(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.376(3) . ?
C21 H21 0.9500 . ?
C21 C20 1.377(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.393(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.373(4) . ?
C29 C33 1.420(3) . ?
C29 C28 1.411(4) . ?
C33 H33 0.9500 . ?
C33 C32 1.347(4) . ?
C4 H4 0.9500 . ?
C32 H32 0.9500 . ?
C32 C31 1.402(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.360(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C31 H31 0.9500 . ?
C28 H28 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.377(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.394(3) . ?
C13 C14 1.512(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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 113.07(8) . . ?
O1 P1 C1 111.80(9) . . ?
O1 P1 C8 115.86(9) . . ?
N1 P1 C1 108.34(8) . . ?
N1 P1 C8 101.48(8) . . ?
C1 P1 C8 105.46(9) . . ?
C15 O2 C9 120.13(16) . . ?
P1 N1 H1 115.2 . . ?
C25 N1 P1 129.65(14) . . ?
C25 N1 H1 115.2 . . ?
C31 N2 C30 117.46(19) . . ?
C8 C9 O2 116.64(17) . . ?
C10 C9 O2 119.44(19) . . ?
C10 C9 C8 123.6(2) . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.41(19) . . ?
C19 C18 H18 119.3 . . ?
C18 C17 H17 119.9 . . ?
C18 C17 C16 120.19(19) . . ?
C16 C17 H17 119.9 . . ?
N1 C25 C30 115.40(17) . . ?
C26 C25 N1 124.85(18) . . ?
C26 C25 C30 119.73(18) . . ?
C2 C1 P1 119.97(14) . . ?
C2 C1 C6 119.49(18) . . ?
C6 C1 P1 120.54(15) . . ?
O2 C15 C16 110.76(16) . . ?
O3 C15 O2 122.3(2) . . ?
O3 C15 C16 126.9(2) . . ?
N2 C30 C25 117.40(17) . . ?
N2 C30 C29 123.14(18) . . ?
C29 C30 C25 119.44(19) . . ?
C17 C16 C15 122.65(19) . . ?
C21 C16 C17 118.65(19) . . ?
C21 C16 C15 118.70(18) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.90(19) . . ?
C3 C2 H2 119.6 . . ?
C9 C8 P1 118.92(15) . . ?
C9 C8 C13 117.61(19) . . ?
C13 C8 P1 123.45(16) . . ?
C1 C6 C7 122.8(2) . . ?
C5 C6 C1 118.13(19) . . ?
C5 C6 C7 119.1(2) . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.0(2) . . ?
C27 C26 H26 120.0 . . ?
C19 C22 H22 107.1 . . ?
C19 C22 C24 114.5(2) . . ?
C19 C22 C23 110.7(2) . . ?
C24 C22 H22 107.1 . . ?
C23 C22 H22 107.1 . . ?
C23 C22 C24 110.0(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.82(19) . . ?
C20 C21 H21 119.6 . . ?
C21 C20 H20 119.4 . . ?
C21 C20 C19 121.1(2) . . ?
C19 C20 H20 119.4 . . ?
C18 C19 C22 118.82(19) . . ?
C20 C19 C18 117.8(2) . . ?
C20 C19 C22 123.4(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 C6 121.7(2) . . ?
C4 C5 H5 119.1 . . ?
C30 C29 C33 116.8(2) . . ?
C30 C29 C28 119.4(2) . . ?
C28 C29 C33 123.8(2) . . ?
C29 C33 H33 120.2 . . ?
C32 C33 C29 119.6(2) . . ?
C32 C33 H33 120.2 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C33 C32 H32 120.3 . . ?
C33 C32 C31 119.5(2) . . ?
C31 C32 H32 120.3 . . ?
C9 C10 H10 121.0 . . ?
C9 C10 C11 118.0(2) . . ?
C11 C10 H10 121.0 . . ?
C26 C27 H27 119.3 . . ?
C28 C27 C26 121.3(2) . . ?
C28 C27 H27 119.3 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C31 C32 123.5(2) . . ?
N2 C31 H31 118.2 . . ?
C32 C31 H31 118.2 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 C29 120.0(2) . . ?
C27 C28 H28 120.0 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.0 . . ?
C11 C12 C13 122.1(2) . . ?
C13 C12 H12 119.0 . . ?
C8 C13 C14 124.2(2) . . ?
C12 C13 C8 118.4(2) . . ?
C12 C13 C14 117.4(2) . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
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 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 N1 C25 C30 -174.94(14) . . . . ?
P1 N1 C25 C26 3.4(3) . . . . ?
P1 C1 C2 C3 -178.97(16) . . . . ?
P1 C1 C6 C5 176.96(16) . . . . ?
P1 C1 C6 C7 -3.5(3) . . . . ?
P1 C8 C13 C12 -178.76(17) . . . . ?
P1 C8 C13 C14 0.5(3) . . . . ?
O2 C9 C8 P1 -9.4(2) . . . . ?
O2 C9 C8 C13 172.35(17) . . . . ?
O2 C9 C10 C11 -171.5(2) . . . . ?
O2 C15 C16 C17 -8.5(3) . . . . ?
O2 C15 C16 C21 171.55(17) . . . . ?
O1 P1 N1 C25 37.4(2) . . . . ?
O1 P1 C1 C2 -116.36(15) . . . . ?
O1 P1 C1 C6 64.06(17) . . . . ?
O1 P1 C8 C9 -177.03(14) . . . . ?
O1 P1 C8 C13 1.1(2) . . . . ?
N1 P1 C1 C2 8.91(17) . . . . ?
N1 P1 C1 C6 -170.68(15) . . . . ?
N1 P1 C8 C9 60.10(16) . . . . ?
N1 P1 C8 C13 -121.75(17) . . . . ?
N1 C25 C30 N2 -0.7(3) . . . . ?
N1 C25 C30 C29 177.67(18) . . . . ?
N1 C25 C26 C27 -178.2(2) . . . . ?
O3 C15 C16 C17 171.3(2) . . . . ?
O3 C15 C16 C21 -8.7(3) . . . . ?
N2 C30 C29 C33 0.5(3) . . . . ?
N2 C30 C29 C28 178.9(2) . . . . ?
C9 O2 C15 O3 -6.2(3) . . . . ?
C9 O2 C15 C16 173.57(15) . . . . ?
C9 C8 C13 C12 -0.6(3) . . . . ?
C9 C8 C13 C14 178.7(2) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C18 C17 C16 C15 -178.29(18) . . . . ?
C18 C17 C16 C21 1.7(3) . . . . ?
C17 C18 C19 C22 179.09(19) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C17 C16 C21 C20 -1.5(3) . . . . ?
C25 C30 C29 C33 -177.7(2) . . . . ?
C25 C30 C29 C28 0.7(3) . . . . ?
C25 C26 C27 C28 0.8(4) . . . . ?
C1 P1 N1 C25 -87.14(18) . . . . ?
C1 P1 C8 C9 -52.81(16) . . . . ?
C1 P1 C8 C13 125.34(17) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
C1 C6 C5 C4 2.4(3) . . . . ?
C15 O2 C9 C8 126.32(18) . . . . ?
C15 O2 C9 C10 -60.2(2) . . . . ?
C15 C16 C21 C20 178.47(18) . . . . ?
C30 N2 C31 C32 1.2(3) . . . . ?
C30 C25 C26 C27 0.0(3) . . . . ?
C30 C29 C33 C32 1.0(3) . . . . ?
C30 C29 C28 C27 0.1(4) . . . . ?
C16 C21 C20 C19 0.0(3) . . . . ?
C2 C1 C6 C5 -2.6(3) . . . . ?
C2 C1 C6 C7 176.9(2) . . . . ?
C2 C3 C4 C5 -2.1(4) . . . . ?
C8 P1 N1 C25 162.13(17) . . . . ?
C8 P1 C1 C2 116.92(15) . . . . ?
C8 P1 C1 C6 -62.67(17) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C6 C5 C4 C3 0.0(4) . . . . ?
C26 C25 C30 N2 -179.10(19) . . . . ?
C26 C25 C30 C29 -0.8(3) . . . . ?
C26 C27 C28 C29 -0.8(5) . . . . ?
C21 C20 C19 C18 1.3(3) . . . . ?
C21 C20 C19 C22 -178.9(2) . . . . ?
C19 C18 C17 C16 -0.4(3) . . . . ?
C29 C33 C32 C31 -1.5(4) . . . . ?
C33 C29 C28 C27 178.4(3) . . . . ?
C33 C32 C31 N2 0.4(4) . . . . ?
C10 C9 C8 P1 177.41(16) . . . . ?
C10 C9 C8 C13 -0.9(3) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C7 C6 C5 C4 -177.2(2) . . . . ?
C31 N2 C30 C25 176.70(19) . . . . ?
C31 N2 C30 C29 -1.6(3) . . . . ?
C28 C29 C33 C32 -177.3(3) . . . . ?
C11 C12 C13 C8 1.3(4) . . . . ?
C11 C12 C13 C14 -178.0(2) . . . . ?
C24 C22 C19 C18 166.7(2) . . . . ?
C24 C22 C19 C20 -13.0(3) . . . . ?
C23 C22 C19 C18 -68.2(3) . . . . ?
C23 C22 C19 C20 112.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
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