# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
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data_s_hxj_2023110201_0m
_database_code_depnum_ccdc_archive 'CCDC 2306225'
loop_
_audit_author_name
_audit_author_address
'chengbo li' 'huaqiao university'
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;
_audit_creation_date             2023-11-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 F N2 O3 S'
_chemical_formula_sum            'C25 H21 F N2 O3 S'
_chemical_formula_weight         448.50
_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 0.0181 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'
S S 0.3331 0.5567 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.8308(3)
_cell_length_b                   12.2131(4)
_cell_length_c                   19.0148(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2050.77(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9792
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      68.303
_cell_measurement_theta_min      4.303
_shelx_estimated_absorpt_T_max   0.579
_shelx_estimated_absorpt_T_min   0.533
_exptl_absorpt_coefficient_mu    1.753
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1028 before and 0.0596 after correction.
The Ratio of minimum to maximum transmission is 0.8103.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20903
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.301
_diffrn_reflns_theta_min         4.302
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 venture microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.11
_diffrn_source_power             0.0555
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3681
_reflns_number_total             3698
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1726 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.043(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3698
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0218
_refine_ls_restrained_S_all      1.067
_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)+(0.0256P)²+0.5182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0575
_refine_ls_wR_factor_ref         0.0576
_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. Others
 Sof(H2)=Sof(F1A)=1-FVAR(1)
 Sof(F1)=Sof(H11)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
S S 0.79299(5) 0.61190(4) 0.57735(3) 0.01609(12) Uani 1 1 d . . . . .
F1 F 0.73390(18) 0.93609(13) 0.74044(9) 0.0344(6) Uani 0.906(6) 1 d . . P A 1
O2 O 0.92892(16) 0.67058(13) 0.55939(8) 0.0251(4) Uani 1 1 d . . . . .
O3 O 0.84514(16) 0.42412(12) 0.42057(8) 0.0196(3) Uani 1 1 d . . . . .
O4 O 0.80212(17) 0.49547(12) 0.58834(8) 0.0235(3) Uani 1 1 d . . . . .
N1 N 0.61090(19) 0.38629(13) 0.46075(10) 0.0164(3) Uani 1 1 d . . . . .
N2 N 0.40919(18) 0.54513(13) 0.40598(9) 0.0151(3) Uani 1 1 d . . . . .
C1 C 0.6099(3) 0.7752(2) 0.77405(12) 0.0264(5) Uani 1 1 d . . . . .
H1 H 0.573936 0.810289 0.815390 0.032 Uiso 1 1 calc R U . . .
C2 C 0.6975(3) 0.83068(19) 0.72618(14) 0.0267(5) Uani 1 1 d . . . . .
H2 H 0.721175 0.905164 0.735478 0.032 Uiso 0.094(6) 1 calc R U P A 2
C3 C 0.7529(2) 0.78417(18) 0.66545(12) 0.0216(4) Uani 1 1 d . . . . .
H3 H 0.812957 0.824792 0.633233 0.026 Uiso 1 1 calc R U . . .
C4 C 0.7169(2) 0.67516(17) 0.65354(11) 0.0172(4) Uani 1 1 d . . . . .
C5 C 0.6495(2) 0.63491(17) 0.51254(10) 0.0145(4) Uani 1 1 d . . . . .
H5A H 0.552415 0.605179 0.530249 0.017 Uiso 1 1 calc R U . . .
H5B H 0.636518 0.714804 0.506141 0.017 Uiso 1 1 calc R U . . .
C6 C 0.6843(2) 0.58207(17) 0.43963(10) 0.0145(4) Uani 1 1 d . . . . .
C7 C 0.7229(2) 0.45742(17) 0.44144(11) 0.0151(4) Uani 1 1 d . . . . .
C8 C 0.4774(2) 0.41637(16) 0.49791(11) 0.0153(4) Uani 1 1 d . . . . .
C9 C 0.4485(2) 0.37047(16) 0.56378(11) 0.0196(4) Uani 1 1 d . . . . .
H9 H 0.520272 0.321989 0.584159 0.024 Uiso 1 1 calc R U . . .
C10 C 0.3164(3) 0.39482(18) 0.59973(12) 0.0214(5) Uani 1 1 d . . . . .
H10 H 0.297923 0.363145 0.644547 0.026 Uiso 1 1 calc R U . . .
C11 C 0.5752(3) 0.6664(2) 0.76034(12) 0.0253(5) Uani 1 1 d . . . . .
H11 H 0.514618 0.626354 0.792648 0.030 Uiso 0.906(6) 1 calc R U P A 1
C12 C 0.6283(3) 0.61541(17) 0.69980(12) 0.0203(4) Uani 1 1 d . . . . .
H12 H 0.604281 0.541038 0.690343 0.024 Uiso 1 1 calc R U . . .
C13 C 0.8198(2) 0.64221(18) 0.40662(12) 0.0185(4) Uani 1 1 d . . . . .
H13A H 0.797906 0.720772 0.404157 0.028 Uiso 1 1 calc R U . . .
H13B H 0.837757 0.613892 0.359122 0.028 Uiso 1 1 calc R U . . .
H13C H 0.910171 0.630266 0.435553 0.028 Uiso 1 1 calc R U . . .
C14 C 0.3734(2) 0.49036(16) 0.46919(11) 0.0154(4) Uani 1 1 d . . . . .
C15 C 0.2401(2) 0.51415(17) 0.50572(11) 0.0175(4) Uani 1 1 d . . . . .
H15 H 0.169022 0.563961 0.486158 0.021 Uiso 1 1 calc R U . . .
C16 C 0.2106(2) 0.46584(17) 0.57014(13) 0.0210(4) Uani 1 1 d . . . . .
H16 H 0.118611 0.481051 0.594095 0.025 Uiso 1 1 calc R U . . .
C17 C 0.5491(2) 0.59476(16) 0.39162(11) 0.0153(4) Uani 1 1 d . . . . .
C18 C 0.5411(2) 0.64803(17) 0.32884(10) 0.0165(4) Uani 1 1 d . . . . .
H18 H 0.620347 0.688476 0.307226 0.020 Uiso 1 1 calc R U . . .
C19 C 0.3925(2) 0.63224(17) 0.30135(11) 0.0168(4) Uani 1 1 d . . . . .
C20 C 0.3113(2) 0.56761(16) 0.34994(11) 0.0162(4) Uani 1 1 d . . . . .
C21 C 0.1632(2) 0.53286(17) 0.33751(11) 0.0189(4) Uani 1 1 d . . . . .
H21 H 0.109994 0.488725 0.370390 0.023 Uiso 1 1 calc R U . . .
C22 C 0.0975(2) 0.56603(17) 0.27460(12) 0.0213(4) Uani 1 1 d . . . . .
H22 H -0.002677 0.543043 0.264021 0.026 Uiso 1 1 calc R U . . .
C23 C 0.1745(3) 0.63223(19) 0.22643(12) 0.0217(5) Uani 1 1 d . . . . .
H23 H 0.125033 0.654150 0.184360 0.026 Uiso 1 1 calc R U . . .
C24 C 0.3209(2) 0.66625(17) 0.23886(11) 0.0194(4) Uani 1 1 d . . . . .
H24 H 0.372342 0.711596 0.206033 0.023 Uiso 1 1 calc R U . . .
C25 C 0.6470(2) 0.26866(17) 0.45613(13) 0.0230(5) Uani 1 1 d . . . . .
H25A H 0.693913 0.253080 0.410511 0.035 Uiso 1 1 calc R U . . .
H25B H 0.553756 0.225796 0.460902 0.035 Uiso 1 1 calc R U . . .
H25C H 0.717354 0.248908 0.493923 0.035 Uiso 1 1 calc R U . . .
F1A F 0.504(2) 0.6310(15) 0.8059(10) 0.052(7) Uani 0.094(6) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S O2 1.4391(16) . ?
S O4 1.4395(15) . ?
S C4 1.774(2) . ?
S C5 1.790(2) . ?
F1 C2 1.354(3) . ?
O3 C7 1.220(3) . ?
N1 C7 1.367(3) . ?
N1 C8 1.423(3) . ?
N1 C25 1.474(3) . ?
N2 C14 1.411(3) . ?
N2 C17 1.403(3) . ?
N2 C20 1.400(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.374(4) . ?
C1 C11 1.388(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 C12 1.385(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.560(3) . ?
C6 C7 1.560(3) . ?
C6 C13 1.538(3) . ?
C6 C17 1.511(3) . ?
C8 C9 1.396(3) . ?
C8 C14 1.399(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9500 . ?
C10 C16 1.393(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(3) . ?
C11 F1A 1.158(17) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.397(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.361(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.426(3) . ?
C19 C20 1.411(3) . ?
C19 C24 1.409(3) . ?
C20 C21 1.395(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.398(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.378(3) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
O2 S O4 118.67(9) . . ?
O2 S C4 107.02(10) . . ?
O2 S C5 110.43(10) . . ?
O4 S C4 109.44(10) . . ?
O4 S C5 107.14(9) . . ?
C4 S C5 103.05(9) . . ?
C7 N1 C8 124.68(17) . . ?
C7 N1 C25 116.55(17) . . ?
C8 N1 C25 117.41(16) . . ?
C17 N2 C14 124.59(17) . . ?
C20 N2 C14 127.09(16) . . ?
C20 N2 C17 108.12(16) . . ?
C2 C1 H1 120.9 . . ?
C2 C1 C11 118.2(2) . . ?
C11 C1 H1 120.9 . . ?
F1 C2 C1 118.0(2) . . ?
F1 C2 C3 118.4(2) . . ?
C1 C2 H2 118.2 . . ?
C1 C2 C3 123.5(2) . . ?
C3 C2 H2 118.2 . . ?
C2 C3 H3 121.6 . . ?
C2 C3 C4 116.8(2) . . ?
C4 C3 H3 121.6 . . ?
C3 C4 S 117.67(16) . . ?
C12 C4 S 120.21(16) . . ?
C12 C4 C3 122.1(2) . . ?
S C5 H5A 108.7 . . ?
S C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 S 114.05(13) . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C5 C6 C7 115.28(16) . . ?
C13 C6 C5 108.58(16) . . ?
C13 C6 C7 107.76(16) . . ?
C17 C6 C5 109.80(16) . . ?
C17 C6 C7 106.62(16) . . ?
C17 C6 C13 108.63(16) . . ?
O3 C7 N1 121.05(19) . . ?
O3 C7 C6 120.75(18) . . ?
N1 C7 C6 117.91(16) . . ?
C9 C8 N1 119.57(18) . . ?
C9 C8 C14 119.32(18) . . ?
C14 C8 N1 121.11(18) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C16 119.9(2) . . ?
C16 C10 H10 120.0 . . ?
C1 C11 H11 119.7 . . ?
C1 C11 C12 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
F1A C11 C1 109.7(10) . . ?
F1A C11 C12 129.6(10) . . ?
C4 C12 C11 118.7(2) . . ?
C4 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 N2 119.44(17) . . ?
C15 C14 N2 120.89(18) . . ?
C15 C14 C8 119.54(19) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C10 C16 H16 120.1 . . ?
C15 C16 C10 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
N2 C17 C6 122.27(17) . . ?
C18 C17 N2 109.36(18) . . ?
C18 C17 C6 128.30(19) . . ?
C17 C18 H18 126.1 . . ?
C17 C18 C19 107.73(18) . . ?
C19 C18 H18 126.1 . . ?
C20 C19 C18 107.67(18) . . ?
C24 C19 C18 133.0(2) . . ?
C24 C19 C20 119.3(2) . . ?
N2 C20 C19 107.10(17) . . ?
C21 C20 N2 130.42(19) . . ?
C21 C20 C19 122.41(19) . . ?
C20 C21 H21 121.7 . . ?
C22 C21 C20 116.6(2) . . ?
C22 C21 H21 121.7 . . ?
C21 C22 H22 119.0 . . ?
C21 C22 C23 122.0(2) . . ?
C23 C22 H22 119.0 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.2(2) . . ?
C24 C23 H23 119.4 . . ?
C19 C24 H24 120.8 . . ?
C23 C24 C19 118.5(2) . . ?
C23 C24 H24 120.8 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
S C4 C12 C11 177.61(16) . . . . ?
S C5 C6 C7 53.0(2) . . . . ?
S C5 C6 C13 -67.96(19) . . . . ?
S C5 C6 C17 173.41(14) . . . . ?
F1 C2 C3 C4 178.2(2) . . . . ?
O2 S C4 C3 25.19(18) . . . . ?
O2 S C4 C12 -153.10(17) . . . . ?
O2 S C5 C6 68.66(16) . . . . ?
O4 S C4 C3 154.99(16) . . . . ?
O4 S C4 C12 -23.31(19) . . . . ?
O4 S C5 C6 -61.93(16) . . . . ?
N1 C8 C9 C10 -177.29(19) . . . . ?
N1 C8 C14 N2 -7.0(3) . . . . ?
N1 C8 C14 C15 177.06(18) . . . . ?
N2 C14 C15 C16 -175.44(18) . . . . ?
N2 C17 C18 C19 -0.3(2) . . . . ?
N2 C20 C21 C22 -177.3(2) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C11 C12 C4 0.2(3) . . . . ?
C2 C1 C11 C12 0.1(3) . . . . ?
C2 C1 C11 F1A 178.7(12) . . . . ?
C2 C3 C4 S -177.64(16) . . . . ?
C2 C3 C4 C12 0.6(3) . . . . ?
C3 C4 C12 C11 -0.6(3) . . . . ?
C4 S C5 C6 -177.33(14) . . . . ?
C5 S C4 C3 -91.27(17) . . . . ?
C5 S C4 C12 90.44(18) . . . . ?
C5 C6 C7 O3 -119.5(2) . . . . ?
C5 C6 C7 N1 66.5(2) . . . . ?
C5 C6 C17 N2 -64.0(2) . . . . ?
C5 C6 C17 C18 119.3(2) . . . . ?
C6 C17 C18 C19 176.70(19) . . . . ?
C7 N1 C8 C9 -119.1(2) . . . . ?
C7 N1 C8 C14 61.6(3) . . . . ?
C7 C6 C17 N2 61.5(2) . . . . ?
C7 C6 C17 C18 -115.2(2) . . . . ?
C8 N1 C7 O3 167.4(2) . . . . ?
C8 N1 C7 C6 -18.7(3) . . . . ?
C8 C9 C10 C16 0.0(3) . . . . ?
C8 C14 C15 C16 0.4(3) . . . . ?
C9 C8 C14 N2 173.75(17) . . . . ?
C9 C8 C14 C15 -2.2(3) . . . . ?
C9 C10 C16 C15 -1.8(3) . . . . ?
C11 C1 C2 F1 -178.6(2) . . . . ?
C11 C1 C2 C3 -0.1(3) . . . . ?
C13 C6 C7 O3 1.9(3) . . . . ?
C13 C6 C7 N1 -172.07(18) . . . . ?
C13 C6 C17 N2 177.41(17) . . . . ?
C13 C6 C17 C18 0.7(3) . . . . ?
C14 N2 C17 C6 8.0(3) . . . . ?
C14 N2 C17 C18 -174.78(18) . . . . ?
C14 N2 C20 C19 174.69(17) . . . . ?
C14 N2 C20 C21 -8.3(3) . . . . ?
C14 C8 C9 C10 2.0(3) . . . . ?
C14 C15 C16 C10 1.6(3) . . . . ?
C17 N2 C14 C8 -45.6(3) . . . . ?
C17 N2 C14 C15 130.3(2) . . . . ?
C17 N2 C20 C19 -0.4(2) . . . . ?
C17 N2 C20 C21 176.6(2) . . . . ?
C17 C6 C7 O3 118.3(2) . . . . ?
C17 C6 C7 N1 -55.6(2) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C17 C18 C19 C24 -179.0(2) . . . . ?
C18 C19 C20 N2 0.2(2) . . . . ?
C18 C19 C20 C21 -177.12(18) . . . . ?
C18 C19 C24 C23 177.1(2) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C20 N2 C14 C8 140.09(19) . . . . ?
C20 N2 C14 C15 -44.0(3) . . . . ?
C20 N2 C17 C6 -176.77(17) . . . . ?
C20 N2 C17 C18 0.5(2) . . . . ?
C20 C19 C24 C23 -1.9(3) . . . . ?
C20 C21 C22 C23 -0.9(3) . . . . ?
C21 C22 C23 C24 1.0(3) . . . . ?
C22 C23 C24 C19 0.4(3) . . . . ?
C24 C19 C20 N2 179.40(17) . . . . ?
C24 C19 C20 C21 2.1(3) . . . . ?
C25 N1 C7 O3 1.0(3) . . . . ?
C25 N1 C7 C6 174.96(17) . . . . ?
C25 N1 C8 C9 47.1(3) . . . . ?
C25 N1 C8 C14 -132.2(2) . . . . ?
F1A C11 C12 C4 -178.0(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_hxj110202
_database_code_depnum_ccdc_archive 'CCDC 2306226'
loop_
_audit_author_name
_audit_author_address
'chengbo li' 'huaqiao university'
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;
_audit_creation_date             2023-11-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H29 N2 O4 P'
_chemical_formula_sum            'C33 H29 N2 O4 P'
_chemical_formula_weight         548.55
_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'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7645(2)
_cell_length_b                   35.2767(6)
_cell_length_c                   8.46120(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.3930(10)
_cell_angle_gamma                90
_cell_volume                     2765.65(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9799
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      68.168
_cell_measurement_theta_min      3.759
_shelx_estimated_absorpt_T_max   0.704
_shelx_estimated_absorpt_T_min   0.654
_exptl_absorpt_coefficient_mu    1.219
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0843 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.8415.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            32848
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.232
_diffrn_reflns_theta_min         2.505
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 venture microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4836
_reflns_number_total             5033
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00059(10)
_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   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5033
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.074
_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)+(0.0378P)²+1.9562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0947
_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:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8), C13(H13), C14(H14), C15(H15), C17(H17),
 C18(H18), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29),
  C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C22(H22A,H22B,H22C), C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.24422(4) 0.33457(2) 0.69203(4) 0.01500(11) Uani 1 1 d . . . . .
O1 O 0.69355(14) 0.52198(3) 0.69951(15) 0.0295(3) Uani 1 1 d . . . . .
O2 O 0.34647(12) 0.30673(3) 0.79980(13) 0.0199(2) Uani 1 1 d . . . . .
O3 O 0.63503(12) 0.35878(3) 0.96827(13) 0.0226(3) Uani 1 1 d . . . . .
O4 O 0.81626(14) 0.55093(3) 0.55068(18) 0.0340(3) Uani 1 1 d . . . . .
N1 N 0.64570(14) 0.33210(4) 0.73045(16) 0.0177(3) Uani 1 1 d . . . . .
N2 N 0.60028(14) 0.39295(4) 0.49592(16) 0.0174(3) Uani 1 1 d . . . . .
C1 C -0.05578(19) 0.27386(5) 0.2321(2) 0.0244(4) Uani 1 1 d . . . . .
H1 H -0.114764 0.261008 0.135990 0.029 Uiso 1 1 calc R U . . .
C2 C 0.0883(2) 0.26424(5) 0.2998(2) 0.0268(4) Uani 1 1 d . . . . .
H2 H 0.127969 0.244654 0.250638 0.032 Uiso 1 1 calc R U . . .
C3 C 0.17469(18) 0.28311(5) 0.4392(2) 0.0235(3) Uani 1 1 d . . . . .
H3 H 0.273497 0.276347 0.485269 0.028 Uiso 1 1 calc R U . . .
C4 C 0.11778(16) 0.31198(4) 0.51235(18) 0.0167(3) Uani 1 1 d . . . . .
C5 C 0.33381(16) 0.36899(4) 0.59881(18) 0.0163(3) Uani 1 1 d . . . . .
H5A H 0.355885 0.356634 0.504610 0.020 Uiso 1 1 calc R U . . .
H5B H 0.265227 0.389869 0.552182 0.020 Uiso 1 1 calc R U . . .
C6 C 0.47610(16) 0.38657(4) 0.71651(18) 0.0172(3) Uani 1 1 d . . . . .
C7 C 0.55248(16) 0.40951(4) 0.61862(18) 0.0168(3) Uani 1 1 d . . . . .
C8 C 0.59270(16) 0.44672(4) 0.63658(19) 0.0188(3) Uani 1 1 d . . . . .
H8 H 0.573051 0.464267 0.711835 0.023 Uiso 1 1 calc R U . . .
C9 C 0.66949(17) 0.45455(4) 0.52218(19) 0.0195(3) Uani 1 1 d . . . . .
C10 C 0.74268(17) 0.48668(4) 0.4871(2) 0.0230(3) Uani 1 1 d . . . . .
C11 C 0.75523(18) 0.52311(5) 0.5793(2) 0.0258(4) Uani 1 1 d . . . . .
C12 C 0.6999(2) 0.55664(5) 0.7928(3) 0.0369(5) Uani 1 1 d . . . . .
H12A H 0.800832 0.563002 0.851639 0.055 Uiso 1 1 calc R U . . .
H12B H 0.647943 0.553161 0.873803 0.055 Uiso 1 1 calc R U . . .
H12C H 0.655067 0.577255 0.716330 0.055 Uiso 1 1 calc R U . . .
C13 C -0.0334(2) 0.39152(6) 0.9695(3) 0.0386(5) Uani 1 1 d . . . . .
H13 H -0.093917 0.402195 1.026500 0.046 Uiso 1 1 calc R U . . .
C14 C 0.0527(2) 0.36079(6) 1.0372(2) 0.0351(4) Uani 1 1 d . . . . .
H14 H 0.054278 0.351037 1.142469 0.042 Uiso 1 1 calc R U . . .
C15 C 0.13669(19) 0.34421(5) 0.9515(2) 0.0251(4) Uani 1 1 d . . . . .
H15 H 0.193932 0.322635 0.996533 0.030 Uiso 1 1 calc R U . . .
C16 C 0.13741(17) 0.35912(5) 0.7994(2) 0.0202(3) Uani 1 1 d . . . . .
C17 C 0.05401(18) 0.39098(5) 0.7340(2) 0.0268(4) Uani 1 1 d . . . . .
H17 H 0.056313 0.401679 0.631801 0.032 Uiso 1 1 calc R U . . .
C18 C -0.03245(19) 0.40697(6) 0.8191(3) 0.0351(4) Uani 1 1 d . . . . .
H18 H -0.090668 0.428410 0.774350 0.042 Uiso 1 1 calc R U . . .
C19 C -0.11407(18) 0.30226(5) 0.3044(2) 0.0264(4) Uani 1 1 d . . . . .
H19 H -0.213108 0.308772 0.258071 0.032 Uiso 1 1 calc R U . . .
C20 C -0.02792(17) 0.32122(5) 0.4445(2) 0.0227(3) Uani 1 1 d . . . . .
H20 H -0.068411 0.340535 0.494265 0.027 Uiso 1 1 calc R U . . .
C21 C 0.58935(16) 0.35742(4) 0.81650(18) 0.0177(3) Uani 1 1 d . . . . .
C22 C 0.75069(18) 0.30498(5) 0.8306(2) 0.0250(4) Uani 1 1 d . . . . .
H22A H 0.810458 0.317356 0.932827 0.037 Uiso 1 1 calc R U . . .
H22B H 0.812266 0.295931 0.766782 0.037 Uiso 1 1 calc R U . . .
H22C H 0.699721 0.283454 0.859507 0.037 Uiso 1 1 calc R U . . .
C23 C 0.59264(16) 0.32544(4) 0.55642(18) 0.0163(3) Uani 1 1 d . . . . .
C24 C 0.55902(16) 0.28842(4) 0.49784(19) 0.0186(3) Uani 1 1 d . . . . .
H24 H 0.572431 0.268171 0.575263 0.022 Uiso 1 1 calc R U . . .
C25 C 0.50647(17) 0.28080(4) 0.3287(2) 0.0203(3) Uani 1 1 d . . . . .
H25 H 0.481795 0.255575 0.291149 0.024 Uiso 1 1 calc R U . . .
C26 C 0.48984(17) 0.30994(5) 0.21406(19) 0.0205(3) Uani 1 1 d . . . . .
H26 H 0.456525 0.304666 0.098049 0.025 Uiso 1 1 calc R U . . .
C27 C 0.52228(16) 0.34693(4) 0.27019(19) 0.0183(3) Uani 1 1 d . . . . .
H27 H 0.509165 0.367002 0.191955 0.022 Uiso 1 1 calc R U . . .
C28 C 0.57397(16) 0.35484(4) 0.44052(19) 0.0163(3) Uani 1 1 d . . . . .
C29 C 0.8111(2) 0.48358(5) 0.3682(2) 0.0303(4) Uani 1 1 d . . . . .
H29 H 0.859938 0.504978 0.343840 0.036 Uiso 1 1 calc R U . . .
C30 C 0.8103(2) 0.44980(5) 0.2829(2) 0.0316(4) Uani 1 1 d . . . . .
H30 H 0.858262 0.448822 0.201229 0.038 Uiso 1 1 calc R U . . .
C31 C 0.74168(18) 0.41757(5) 0.3135(2) 0.0249(4) Uani 1 1 d . . . . .
H31 H 0.742004 0.394545 0.255381 0.030 Uiso 1 1 calc R U . . .
C32 C 0.67202(17) 0.42055(4) 0.4339(2) 0.0194(3) Uani 1 1 d . . . . .
C33 C 0.43809(18) 0.41260(5) 0.8420(2) 0.0214(3) Uani 1 1 d . . . . .
H33A H 0.526219 0.424500 0.914520 0.032 Uiso 1 1 calc R U . . .
H33B H 0.392875 0.397633 0.909586 0.032 Uiso 1 1 calc R U . . .
H33C H 0.370893 0.432277 0.781870 0.032 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 1.4896(11) . ?
P1 C4 1.8129(15) . ?
P1 C5 1.8155(15) . ?
P1 C16 1.8056(16) . ?
O1 C11 1.336(2) . ?
O1 C12 1.447(2) . ?
O3 C21 1.2202(19) . ?
O4 C11 1.212(2) . ?
N1 C21 1.372(2) . ?
N1 C22 1.462(2) . ?
N1 C23 1.4179(19) . ?
N2 C7 1.394(2) . ?
N2 C28 1.4201(19) . ?
N2 C32 1.395(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.383(3) . ?
C1 C19 1.386(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(2) . ?
C4 C20 1.394(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.560(2) . ?
C6 C7 1.512(2) . ?
C6 C21 1.551(2) . ?
C6 C33 1.535(2) . ?
C7 C8 1.365(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.426(2) . ?
C9 C10 1.420(2) . ?
C9 C32 1.417(2) . ?
C10 C11 1.488(2) . ?
C10 C29 1.376(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.381(3) . ?
C13 C18 1.388(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.393(2) . ?
C16 C17 1.396(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.390(2) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.398(2) . ?
C23 C28 1.399(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.390(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.397(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.392(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.385(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.396(2) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
O2 P1 C4 111.77(7) . . ?
O2 P1 C5 112.65(7) . . ?
O2 P1 C16 112.97(7) . . ?
C4 P1 C5 102.93(7) . . ?
C16 P1 C4 106.50(7) . . ?
C16 P1 C5 109.38(7) . . ?
C11 O1 C12 116.01(14) . . ?
C21 N1 C22 116.33(13) . . ?
C21 N1 C23 125.63(13) . . ?
C23 N1 C22 116.95(13) . . ?
C7 N2 C28 125.06(12) . . ?
C7 N2 C32 108.26(12) . . ?
C32 N2 C28 126.64(13) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C19 119.98(15) . . ?
C19 C1 H1 120.0 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.11(16) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.52(15) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 P1 115.59(12) . . ?
C20 C4 P1 125.36(12) . . ?
C20 C4 C3 119.05(14) . . ?
P1 C5 H5A 108.2 . . ?
P1 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
C6 C5 P1 116.28(10) . . ?
C6 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
C7 C6 C5 110.91(12) . . ?
C7 C6 C21 105.28(12) . . ?
C7 C6 C33 109.11(12) . . ?
C21 C6 C5 115.00(12) . . ?
C33 C6 C5 108.56(13) . . ?
C33 C6 C21 107.80(12) . . ?
N2 C7 C6 121.51(13) . . ?
C8 C7 N2 109.50(13) . . ?
C8 C7 C6 128.90(14) . . ?
C7 C8 H8 126.1 . . ?
C7 C8 C9 107.78(14) . . ?
C9 C8 H8 126.1 . . ?
C10 C9 C8 134.70(15) . . ?
C32 C9 C8 107.09(13) . . ?
C32 C9 C10 118.16(15) . . ?
C9 C10 C11 122.92(15) . . ?
C29 C10 C9 118.77(15) . . ?
C29 C10 C11 118.24(15) . . ?
O1 C11 C10 113.00(14) . . ?
O4 C11 O1 123.00(16) . . ?
O4 C11 C10 123.99(17) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 H13 119.7 . . ?
C14 C13 C18 120.63(17) . . ?
C18 C13 H13 119.7 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.88(18) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.10(18) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 P1 117.14(13) . . ?
C15 C16 C17 119.87(15) . . ?
C17 C16 P1 122.96(13) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.67(17) . . ?
C18 C17 H17 120.2 . . ?
C13 C18 C17 119.79(18) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C1 C19 H19 119.9 . . ?
C1 C19 C20 120.15(15) . . ?
C20 C19 H19 119.9 . . ?
C4 C20 H20 119.9 . . ?
C19 C20 C4 120.18(15) . . ?
C19 C20 H20 119.9 . . ?
O3 C21 N1 120.61(14) . . ?
O3 C21 C6 120.60(14) . . ?
N1 C21 C6 118.58(13) . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 N1 119.40(13) . . ?
C24 C23 C28 118.66(14) . . ?
C28 C23 N1 121.93(13) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 121.08(14) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.12(14) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.53(14) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.61(14) . . ?
C28 C27 H27 119.7 . . ?
C23 C28 N2 120.03(13) . . ?
C27 C28 N2 119.91(13) . . ?
C27 C28 C23 119.98(14) . . ?
C10 C29 H29 119.2 . . ?
C10 C29 C30 121.52(16) . . ?
C30 C29 H29 119.2 . . ?
C29 C30 H30 119.0 . . ?
C31 C30 C29 121.98(16) . . ?
C31 C30 H30 119.0 . . ?
C30 C31 H31 121.6 . . ?
C30 C31 C32 116.77(16) . . ?
C32 C31 H31 121.6 . . ?
N2 C32 C9 107.36(13) . . ?
N2 C32 C31 129.78(15) . . ?
C31 C32 C9 122.81(14) . . ?
C6 C33 H33A 109.5 . . ?
C6 C33 H33B 109.5 . . ?
C6 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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 C4 C20 C19 178.96(13) . . . . ?
P1 C5 C6 C7 170.53(10) . . . . ?
P1 C5 C6 C21 51.22(16) . . . . ?
P1 C5 C6 C33 -69.61(14) . . . . ?
P1 C16 C17 C18 176.02(13) . . . . ?
O2 P1 C4 C3 -38.69(14) . . . . ?
O2 P1 C4 C20 141.31(13) . . . . ?
O2 P1 C5 C6 -44.63(13) . . . . ?
O2 P1 C16 C15 -14.00(15) . . . . ?
O2 P1 C16 C17 168.11(13) . . . . ?
N1 C23 C24 C25 179.79(14) . . . . ?
N1 C23 C28 N2 -3.7(2) . . . . ?
N1 C23 C28 C27 179.57(14) . . . . ?
N2 C7 C8 C9 -0.17(17) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C19 C20 C4 0.5(3) . . . . ?
C2 C1 C19 C20 0.3(3) . . . . ?
C2 C3 C4 P1 -179.13(13) . . . . ?
C2 C3 C4 C20 0.9(2) . . . . ?
C3 C4 C20 C19 -1.0(2) . . . . ?
C4 P1 C5 C6 -165.17(11) . . . . ?
C4 P1 C16 C15 109.08(13) . . . . ?
C4 P1 C16 C17 -68.82(15) . . . . ?
C5 P1 C4 C3 82.46(13) . . . . ?
C5 P1 C4 C20 -97.54(14) . . . . ?
C5 P1 C16 C15 -140.34(12) . . . . ?
C5 P1 C16 C17 41.76(15) . . . . ?
C5 C6 C7 N2 -60.80(18) . . . . ?
C5 C6 C7 C8 123.05(17) . . . . ?
C5 C6 C21 O3 -123.32(15) . . . . ?
C5 C6 C21 N1 61.96(17) . . . . ?
C6 C7 C8 C9 176.35(14) . . . . ?
C7 N2 C28 C23 -45.3(2) . . . . ?
C7 N2 C28 C27 131.38(16) . . . . ?
C7 N2 C32 C9 0.73(17) . . . . ?
C7 N2 C32 C31 178.17(16) . . . . ?
C7 C6 C21 O3 114.29(15) . . . . ?
C7 C6 C21 N1 -60.44(16) . . . . ?
C7 C8 C9 C10 -176.55(17) . . . . ?
C7 C8 C9 C32 0.62(17) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C8 C9 C10 C29 177.71(18) . . . . ?
C8 C9 C32 N2 -0.83(17) . . . . ?
C8 C9 C32 C31 -178.49(15) . . . . ?
C9 C10 C11 O1 1.4(2) . . . . ?
C9 C10 C11 O4 -179.46(16) . . . . ?
C9 C10 C29 C30 -0.2(3) . . . . ?
C10 C9 C32 N2 176.89(13) . . . . ?
C10 C9 C32 C31 -0.8(2) . . . . ?
C10 C29 C30 C31 -0.4(3) . . . . ?
C11 C10 C29 C30 176.72(17) . . . . ?
C12 O1 C11 O4 1.7(2) . . . . ?
C12 O1 C11 C10 -179.15(15) . . . . ?
C13 C14 C15 C16 1.7(3) . . . . ?
C14 C13 C18 C17 1.2(3) . . . . ?
C14 C15 C16 P1 -177.52(13) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C18 -1.8(2) . . . . ?
C16 P1 C4 C3 -162.51(12) . . . . ?
C16 P1 C4 C20 17.49(16) . . . . ?
C16 P1 C5 C6 81.89(12) . . . . ?
C16 C17 C18 C13 1.0(3) . . . . ?
C18 C13 C14 C15 -2.6(3) . . . . ?
C19 C1 C2 C3 -0.4(3) . . . . ?
C21 N1 C23 C24 -126.49(16) . . . . ?
C21 N1 C23 C28 54.1(2) . . . . ?
C21 C6 C7 N2 64.19(17) . . . . ?
C21 C6 C7 C8 -111.96(17) . . . . ?
C22 N1 C21 O3 6.0(2) . . . . ?
C22 N1 C21 C6 -179.30(13) . . . . ?
C22 N1 C23 C24 41.1(2) . . . . ?
C22 N1 C23 C28 -138.26(15) . . . . ?
C23 N1 C21 O3 173.66(14) . . . . ?
C23 N1 C21 C6 -11.6(2) . . . . ?
C23 C24 C25 C26 1.7(2) . . . . ?
C24 C23 C28 N2 176.88(14) . . . . ?
C24 C23 C28 C27 0.2(2) . . . . ?
C24 C25 C26 C27 -1.9(2) . . . . ?
C25 C26 C27 C28 1.2(2) . . . . ?
C26 C27 C28 N2 -177.10(14) . . . . ?
C26 C27 C28 C23 -0.4(2) . . . . ?
C28 N2 C7 C6 5.2(2) . . . . ?
C28 N2 C7 C8 -177.95(14) . . . . ?
C28 N2 C32 C9 178.28(14) . . . . ?
C28 N2 C32 C31 -4.3(3) . . . . ?
C28 C23 C24 C25 -0.8(2) . . . . ?
C29 C10 C11 O1 -175.46(15) . . . . ?
C29 C10 C11 O4 3.7(3) . . . . ?
C29 C30 C31 C32 0.4(3) . . . . ?
C30 C31 C32 N2 -176.91(17) . . . . ?
C30 C31 C32 C9 0.2(2) . . . . ?
C32 N2 C7 C6 -177.18(13) . . . . ?
C32 N2 C7 C8 -0.35(17) . . . . ?
C32 N2 C28 C23 137.53(16) . . . . ?
C32 N2 C28 C27 -45.8(2) . . . . ?
C32 C9 C10 C11 -176.04(15) . . . . ?
C32 C9 C10 C29 0.8(2) . . . . ?
C33 C6 C7 N2 179.66(13) . . . . ?
C33 C6 C7 C8 3.5(2) . . . . ?
C33 C6 C21 O3 -2.08(19) . . . . ?
C33 C6 C21 N1 -176.81(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
