# Electronic Supplementary Material (ESI) for Chemical Science.
# 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).
# 
# 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_mo_d8v19139_0m
_database_code_depnum_ccdc_archive 'CCDC 2203561'
loop_
_audit_author_name
_audit_author_address
'Guangfan Zheng'
;NENU
China
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H23 Br Cl3 N2 O2 P'
_chemical_formula_weight         684.75

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3848(2)
_cell_length_b                   11.5366(3)
_cell_length_c                   14.8861(4)
_cell_angle_alpha                79.7470(10)
_cell_angle_beta                 83.5210(10)
_cell_angle_gamma                72.5000(10)
_cell_volume                     1509.54(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      4.997
_cell_measurement_theta_max      55.032

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.713
_shelx_estimated_absorpt_T_min   0.771
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5557
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22100
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.498
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5895
_reflns_number_gt                5238
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²+0.6965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0103(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5895
_refine_ls_number_parameters     376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Br1 Br 0.06489(2) 1.15566(2) 0.30131(2) 0.03661(9) Uani 1 1 d . . . . .
P1 P 0.42673(5) 0.92235(4) 0.89063(3) 0.02327(12) Uani 1 1 d . . . . .
O1 O 0.2752(2) 0.57150(13) 0.53985(10) 0.0421(4) Uani 1 1 d . . . . .
O2 O 0.47391(15) 0.84878(12) 0.98023(9) 0.0297(3) Uani 1 1 d . . . . .
N1 N 0.34294(18) 0.67322(13) 0.63818(10) 0.0246(3) Uani 1 1 d . . . . .
N2 N 0.2777(2) 0.57069(16) 0.77919(12) 0.0370(4) Uani 1 1 d . . . . .
C1 C 0.2860(2) 0.66876(17) 0.55666(13) 0.0277(4) Uani 1 1 d . . . . .
C2 C 0.2393(2) 0.78526(16) 0.49515(12) 0.0235(4) Uani 1 1 d . . . . .
C3 C 0.1830(2) 0.78723(18) 0.41148(13) 0.0277(4) Uani 1 1 d . . . . .
H3 H 0.1786 0.7128 0.3947 0.033 Uiso 1 1 calc R U . . .
C4 C 0.1340(2) 0.89591(18) 0.35362(13) 0.0294(4) Uani 1 1 d . . . . .
H4 H 0.0963 0.8971 0.2967 0.035 Uiso 1 1 calc R U . . .
C5 C 0.1402(2) 1.00459(18) 0.37945(13) 0.0272(4) Uani 1 1 d . . . . .
C6 C 0.1971(2) 1.00577(17) 0.46018(13) 0.0271(4) Uani 1 1 d . . . . .
H6 H 0.2019 1.0808 0.4757 0.032 Uiso 1 1 calc R U . . .
C7 C 0.2480(2) 0.89499(17) 0.51942(12) 0.0240(4) Uani 1 1 d . . . . .
C8 C 0.3122(2) 0.88868(17) 0.60376(13) 0.0260(4) Uani 1 1 d . . . . .
H8 H 0.3227 0.9616 0.6198 0.031 Uiso 1 1 calc R U . . .
C9 C 0.3579(2) 0.78200(16) 0.66068(13) 0.0241(4) Uani 1 1 d . . . . .
C10 C 0.4321(2) 0.77622(16) 0.74484(13) 0.0257(4) Uani 1 1 d . . . . .
C11 C 0.3696(2) 0.86158(17) 0.80006(13) 0.0261(4) Uani 1 1 d . . . . .
C12 C 0.2245(2) 0.95401(18) 0.80595(14) 0.0289(4) Uani 1 1 d . . . . .
C13 C 0.2336(2) 1.01141(17) 0.87608(13) 0.0259(4) Uani 1 1 d . . . . .
C14 C 0.1251(2) 1.10318(17) 0.92369(13) 0.0263(4) Uani 1 1 d . . . . .
C15 C -0.0281(2) 1.12860(19) 0.91395(15) 0.0344(5) Uani 1 1 d . . . . .
H15 H -0.0618 1.0910 0.8720 0.041 Uiso 1 1 calc R U . . .
C16 C -0.1311(3) 1.2086(2) 0.96543(17) 0.0450(6) Uani 1 1 d . . . . .
H16 H -0.2351 1.2261 0.9583 0.054 Uiso 1 1 calc R U . . .
C17 C -0.0830(3) 1.2628(2) 1.02679(17) 0.0491(6) Uani 1 1 d . . . . .
H17 H -0.1541 1.3155 1.0634 0.059 Uiso 1 1 calc R U . . .
C18 C 0.0680(3) 1.2409(2) 1.03538(16) 0.0453(6) Uani 1 1 d . . . . .
H18 H 0.1006 1.2804 1.0766 0.054 Uiso 1 1 calc R U . . .
C19 C 0.1724(3) 1.16139(19) 0.98400(14) 0.0340(5) Uani 1 1 d . . . . .
H19 H 0.2763 1.1467 0.9900 0.041 Uiso 1 1 calc R U . . .
C20 C 0.5518(2) 1.00936(18) 0.83785(14) 0.0317(4) Uani 1 1 d . . . . .
H20A H 0.5636 1.0615 0.8801 0.048 Uiso 1 1 calc R U . . .
H20B H 0.5106 1.0611 0.7817 0.048 Uiso 1 1 calc R U . . .
H20C H 0.6495 0.9530 0.8229 0.048 Uiso 1 1 calc R U . . .
C21 C 0.3704(2) 0.56300(16) 0.70549(13) 0.0268(4) Uani 1 1 d . . . . .
C22 C 0.4882(2) 0.46121(18) 0.69003(14) 0.0326(4) Uani 1 1 d . . . . .
H22 H 0.5485 0.4599 0.6343 0.039 Uiso 1 1 calc R U . . .
C23 C 0.5145(3) 0.36146(19) 0.75916(16) 0.0424(5) Uani 1 1 d . . . . .
H23 H 0.5952 0.2899 0.7523 0.051 Uiso 1 1 calc R U . . .
C24 C 0.4226(3) 0.3669(2) 0.83820(16) 0.0480(6) Uani 1 1 d . . . . .
H24 H 0.4397 0.3001 0.8871 0.058 Uiso 1 1 calc R U . . .
C25 C 0.3057(3) 0.4709(2) 0.84460(16) 0.0472(6) Uani 1 1 d . . . . .
H25 H 0.2406 0.4729 0.8984 0.057 Uiso 1 1 calc R U . . .
C26 C 0.5776(2) 0.68315(17) 0.76397(14) 0.0285(4) Uani 1 1 d . . . . .
C27 C 0.6849(2) 0.64745(19) 0.69400(15) 0.0360(5) Uani 1 1 d . . . . .
H27 H 0.6655 0.6832 0.6324 0.043 Uiso 1 1 calc R U . . .
C28 C 0.8202(3) 0.5599(2) 0.71379(19) 0.0487(6) Uani 1 1 d . . . . .
H28 H 0.8933 0.5363 0.6657 0.058 Uiso 1 1 calc R U . . .
C29 C 0.8489(3) 0.5069(2) 0.8030(2) 0.0571(7) Uani 1 1 d . . . . .
H29 H 0.9416 0.4471 0.8164 0.069 Uiso 1 1 calc R U . . .
C30 C 0.7427(3) 0.5412(2) 0.87238(18) 0.0595(8) Uani 1 1 d . . . . .
H30 H 0.7624 0.5044 0.9338 0.071 Uiso 1 1 calc R U . . .
C31 C 0.6081(3) 0.6284(2) 0.85377(15) 0.0442(6) Uani 1 1 d . . . . .
H31 H 0.5358 0.6514 0.9023 0.053 Uiso 1 1 calc R U . . .
Cl1 Cl 0.10439(7) 0.33932(6) 0.52572(4) 0.05063(16) Uani 1 1 d . . . . .
Cl2 Cl 0.40652(7) 0.21212(7) 0.57503(5) 0.05881(19) Uani 1 1 d . . . . .
Cl3 Cl 0.16877(8) 0.26546(7) 0.71504(5) 0.06051(19) Uani 1 1 d . . . . .
C32 C 0.2369(2) 0.31769(19) 0.60580(15) 0.0355(5) Uani 1 1 d . . . . .
H32 H 0.2556 0.3983 0.6068 0.043 Uiso 1 1 calc R U . . .
H12 H 0.149(3) 0.967(2) 0.7689(15) 0.030(6) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C5 1.9007(19) . ?
P1 O2 1.4831(14) . ?
P1 C20 1.795(2) . ?
P1 C13 1.810(2) . ?
P1 C11 1.8229(18) . ?
P1 C12 2.299(2) . ?
O1 C1 1.227(2) . ?
N1 C1 1.395(2) . ?
N1 C9 1.405(2) . ?
N1 C21 1.447(2) . ?
N2 C21 1.320(3) . ?
N2 C25 1.348(3) . ?
C1 C2 1.461(3) . ?
C2 C3 1.401(3) . ?
C2 C7 1.404(3) . ?
C3 C4 1.372(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(3) . ?
C6 C7 1.402(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.434(3) . ?
C8 C9 1.345(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.483(3) . ?
C10 C11 1.350(3) . ?
C10 C26 1.481(3) . ?
C11 C12 1.460(3) . ?
C12 C13 1.355(3) . ?
C12 H12 0.91(2) . ?
C13 C14 1.454(3) . ?
C14 C19 1.392(3) . ?
C14 C15 1.398(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.383(3) . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.377(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.371(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C31 1.395(3) . ?
C26 C27 1.391(3) . ?
C27 C28 1.388(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.379(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.376(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.378(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
Cl1 C32 1.752(2) . ?
Cl2 C32 1.759(2) . ?
Cl3 C32 1.751(2) . ?
C32 H32 1.0000 . ?

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 C20 113.27(9) . . ?
O2 P1 C13 120.71(9) . . ?
C20 P1 C13 110.93(9) . . ?
O2 P1 C11 123.90(8) . . ?
C20 P1 C11 107.01(9) . . ?
C13 P1 C11 75.44(9) . . ?
O2 P1 C12 134.04(8) . . ?
C20 P1 C12 112.66(9) . . ?
C13 P1 C12 36.09(8) . . ?
C11 P1 C12 39.41(8) . . ?
C1 N1 C9 122.86(15) . . ?
C1 N1 C21 117.06(15) . . ?
C9 N1 C21 119.68(15) . . ?
C21 N2 C25 115.74(19) . . ?
O1 C1 N1 120.58(18) . . ?
O1 C1 C2 123.19(17) . . ?
N1 C1 C2 116.22(15) . . ?
C3 C2 C7 119.80(17) . . ?
C3 C2 C1 119.27(16) . . ?
C7 C2 C1 120.93(16) . . ?
C4 C3 C2 120.52(17) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.10(18) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.92(18) . . ?
C6 C5 Br1 119.13(15) . . ?
C4 C5 Br1 118.94(14) . . ?
C5 C6 C7 119.27(17) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C2 119.36(17) . . ?
C6 C7 C8 122.39(17) . . ?
C2 C7 C8 118.24(17) . . ?
C9 C8 C7 121.63(17) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 N1 120.02(16) . . ?
C8 C9 C10 120.70(16) . . ?
N1 C9 C10 119.19(16) . . ?
C11 C10 C26 121.02(17) . . ?
C11 C10 C9 118.81(17) . . ?
C26 C10 C9 120.05(16) . . ?
C10 C11 C12 134.01(18) . . ?
C10 C11 P1 137.65(16) . . ?
C12 C11 P1 88.17(12) . . ?
C13 C12 C11 104.24(17) . . ?
C13 C12 P1 51.91(11) . . ?
C11 C12 P1 52.43(9) . . ?
C13 C12 H12 130.7(14) . . ?
C11 C12 H12 125.1(14) . . ?
P1 C12 H12 175.9(14) . . ?
C12 C13 C14 133.07(18) . . ?
C12 C13 P1 91.99(13) . . ?
C14 C13 P1 134.83(14) . . ?
C19 C14 C15 119.10(18) . . ?
C19 C14 C13 120.18(18) . . ?
C15 C14 C13 120.61(18) . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.1(2) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
P1 C20 H20A 109.5 . . ?
P1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
P1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 125.33(18) . . ?
N2 C21 N1 114.85(17) . . ?
C22 C21 N1 119.81(17) . . ?
C23 C22 C21 117.1(2) . . ?
C23 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
C24 C23 C22 119.3(2) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 118.4(2) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
N2 C25 C24 123.9(2) . . ?
N2 C25 H25 118.0 . . ?
C24 C25 H25 118.0 . . ?
C31 C26 C27 118.74(19) . . ?
C31 C26 C10 119.77(19) . . ?
C27 C26 C10 121.48(18) . . ?
C28 C27 C26 120.3(2) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C27 120.2(2) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 119.7(2) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 120.7(2) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C26 120.3(2) . . ?
C30 C31 H31 119.8 . . ?
C26 C31 H31 119.8 . . ?
Cl1 C32 Cl3 110.19(12) . . ?
Cl1 C32 Cl2 110.40(12) . . ?
Cl3 C32 Cl2 110.15(12) . . ?
Cl1 C32 H32 108.7 . . ?
Cl3 C32 H32 108.7 . . ?
Cl2 C32 H32 108.7 . . ?

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
C9 N1 C1 O1 179.90(19) . . . . ?
C21 N1 C1 O1 -7.4(3) . . . . ?
C9 N1 C1 C2 -1.0(3) . . . . ?
C21 N1 C1 C2 171.69(17) . . . . ?
O1 C1 C2 C3 -1.8(3) . . . . ?
N1 C1 C2 C3 179.13(17) . . . . ?
O1 C1 C2 C7 177.2(2) . . . . ?
N1 C1 C2 C7 -1.8(3) . . . . ?
C7 C2 C3 C4 -1.0(3) . . . . ?
C1 C2 C3 C4 177.99(18) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C3 C4 C5 Br1 -177.54(15) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
Br1 C5 C6 C7 177.85(14) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C5 C6 C7 C8 178.43(18) . . . . ?
C3 C2 C7 C6 1.4(3) . . . . ?
C1 C2 C7 C6 -177.67(18) . . . . ?
C3 C2 C7 C8 -177.38(18) . . . . ?
C1 C2 C7 C8 3.6(3) . . . . ?
C6 C7 C8 C9 178.68(19) . . . . ?
C2 C7 C8 C9 -2.6(3) . . . . ?
C7 C8 C9 N1 -0.1(3) . . . . ?
C7 C8 C9 C10 176.34(18) . . . . ?
C1 N1 C9 C8 2.0(3) . . . . ?
C21 N1 C9 C8 -170.50(18) . . . . ?
C1 N1 C9 C10 -174.50(17) . . . . ?
C21 N1 C9 C10 13.0(3) . . . . ?
C8 C9 C10 C11 47.9(3) . . . . ?
N1 C9 C10 C11 -135.63(19) . . . . ?
C8 C9 C10 C26 -128.1(2) . . . . ?
N1 C9 C10 C26 48.4(3) . . . . ?
C26 C10 C11 C12 -171.9(2) . . . . ?
C9 C10 C11 C12 12.2(3) . . . . ?
C26 C10 C11 P1 14.6(3) . . . . ?
C9 C10 C11 P1 -161.34(17) . . . . ?
O2 P1 C11 C10 -64.5(3) . . . . ?
C20 P1 C11 C10 70.2(2) . . . . ?
C13 P1 C11 C10 178.0(2) . . . . ?
C12 P1 C11 C10 175.4(3) . . . . ?
O2 P1 C11 C12 120.10(13) . . . . ?
C20 P1 C11 C12 -105.21(13) . . . . ?
C13 P1 C11 C12 2.64(12) . . . . ?
C10 C11 C12 C13 -179.2(2) . . . . ?
P1 C11 C12 C13 -3.52(16) . . . . ?
C10 C11 C12 P1 -175.7(3) . . . . ?
C11 C12 C13 C14 -173.0(2) . . . . ?
P1 C12 C13 C14 -176.6(3) . . . . ?
C11 C12 C13 P1 3.55(16) . . . . ?
O2 P1 C13 C12 -123.91(13) . . . . ?
C20 P1 C13 C12 100.11(14) . . . . ?
C11 P1 C13 C12 -2.85(13) . . . . ?
O2 P1 C13 C14 52.6(2) . . . . ?
C20 P1 C13 C14 -83.4(2) . . . . ?
C11 P1 C13 C14 173.6(2) . . . . ?
C12 P1 C13 C14 176.5(3) . . . . ?
C12 C13 C14 C19 -169.1(2) . . . . ?
P1 C13 C14 C19 15.8(3) . . . . ?
C12 C13 C14 C15 14.9(3) . . . . ?
P1 C13 C14 C15 -160.28(17) . . . . ?
C19 C14 C15 C16 -1.5(3) . . . . ?
C13 C14 C15 C16 174.63(19) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 2.1(4) . . . . ?
C16 C17 C18 C19 -1.8(4) . . . . ?
C17 C18 C19 C14 -0.1(3) . . . . ?
C15 C14 C19 C18 1.7(3) . . . . ?
C13 C14 C19 C18 -174.4(2) . . . . ?
C25 N2 C21 C22 2.0(3) . . . . ?
C25 N2 C21 N1 -177.02(19) . . . . ?
C1 N1 C21 N2 -109.5(2) . . . . ?
C9 N1 C21 N2 63.5(2) . . . . ?
C1 N1 C21 C22 71.4(2) . . . . ?
C9 N1 C21 C22 -115.6(2) . . . . ?
N2 C21 C22 C23 -2.9(3) . . . . ?
N1 C21 C22 C23 176.12(18) . . . . ?
C21 C22 C23 C24 1.1(3) . . . . ?
C22 C23 C24 C25 1.3(4) . . . . ?
C21 N2 C25 C24 0.6(4) . . . . ?
C23 C24 C25 N2 -2.2(4) . . . . ?
C11 C10 C26 C31 40.4(3) . . . . ?
C9 C10 C26 C31 -143.8(2) . . . . ?
C11 C10 C26 C27 -140.4(2) . . . . ?
C9 C10 C26 C27 35.5(3) . . . . ?
C31 C26 C27 C28 -0.6(3) . . . . ?
C10 C26 C27 C28 -179.9(2) . . . . ?
C26 C27 C28 C29 0.4(4) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
C28 C29 C30 C31 -0.3(4) . . . . ?
C29 C30 C31 C26 0.1(4) . . . . ?
C27 C26 C31 C30 0.4(3) . . . . ?
C10 C26 C31 C30 179.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C32 H32 O1 1.00 2.12 3.033(2) 151.0 .
C24 H24 O2 0.95 2.41 3.344(3) 166.6 2_667
C20 H20A O2 0.98 2.43 3.356(2) 157.7 2_677

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_d8v19140_0m
_database_code_depnum_ccdc_archive 'CCDC 2203562'
loop_
_audit_author_name
_audit_author_address
'Guangfan Zheng'
;SNNU
China
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H26 Cl2 N3 O3 P'
_chemical_formula_weight         602.43

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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3078(2)
_cell_length_b                   12.9452(3)
_cell_length_c                   13.3909(3)
_cell_angle_alpha                83.5890(10)
_cell_angle_beta                 79.8970(10)
_cell_angle_gamma                69.5020(10)
_cell_volume                     1485.69(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      4.693
_cell_measurement_theta_max      54.943

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.310
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4940
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21981
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5519
_reflns_number_gt                4672
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+0.8159P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5519
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cl1 Cl 0.8911(6) 0.7191(4) 0.3527(4) 0.0756(10) Uani 0.6 1 d . . P A 1
Cl1' Cl 0.8949(10) 0.7189(7) 0.3865(7) 0.124(3) Uani 0.4 1 d . . P A 2
Cl2 Cl 0.61104(10) 0.90028(6) 0.41264(7) 0.0750(3) Uani 1 1 d . . . . .
C32 C 0.6993(4) 0.7581(2) 0.4190(2) 0.0548(7) Uani 1 1 d . . . . .
P1 P 0.53761(6) 0.09746(4) 0.12079(4) 0.02626(16) Uani 1 1 d . . . . .
O1 O 0.48861(17) 0.14715(12) 0.02159(10) 0.0350(3) Uani 1 1 d . . . . .
O2 O 0.7341(2) 0.60594(13) 0.61815(12) 0.0507(5) Uani 1 1 d . . . . .
O3 O 0.79611(18) 0.47289(12) 0.74067(11) 0.0392(4) Uani 1 1 d . . . . .
N1 N 0.67629(19) 0.37193(13) 0.33742(12) 0.0270(4) Uani 1 1 d . . . . .
N2 N 0.7155(3) 0.53664(16) 0.27531(14) 0.0453(5) Uani 1 1 d . . . . .
N3 N 0.5610(2) 0.46497(14) 0.19861(13) 0.0337(4) Uani 1 1 d . . . . .
C1 C 0.6907(2) 0.37304(15) 0.44026(14) 0.0265(4) Uani 1 1 d . . . . .
C2 C 0.7096(2) 0.45265(16) 0.49290(15) 0.0303(4) Uani 1 1 d . . . . .
H2 H 0.7129 0.5210 0.4603 0.036 Uiso 1 1 calc R U . . .
C3 C 0.7235(2) 0.42851(16) 0.59543(15) 0.0299(4) Uani 1 1 d . . . . .
C4 C 0.7155(2) 0.32857(17) 0.64418(15) 0.0313(4) Uani 1 1 d . . . . .
H4 H 0.7248 0.3144 0.7143 0.038 Uiso 1 1 calc R U . . .
C5 C 0.6942(2) 0.25086(16) 0.59176(15) 0.0298(4) Uani 1 1 d . . . . .
H5 H 0.6881 0.1835 0.6252 0.036 Uiso 1 1 calc R U . . .
C6 C 0.6817(2) 0.27257(15) 0.48800(14) 0.0260(4) Uani 1 1 d . . . . .
C7 C 0.6650(2) 0.20996(16) 0.41273(14) 0.0272(4) Uani 1 1 d . . . . .
H7 H 0.6571 0.1382 0.4236 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6622(2) 0.27005(15) 0.32263(14) 0.0262(4) Uani 1 1 d . . . . .
C9 C 0.6659(2) 0.23246(15) 0.22201(14) 0.0266(4) Uani 1 1 d . . . . .
C10 C 0.5695(2) 0.17778(15) 0.21312(14) 0.0271(4) Uani 1 1 d . . . . .
C11 C 0.4443(2) 0.15518(17) 0.28279(15) 0.0302(4) Uani 1 1 d . . . . .
C12 C 0.3934(2) 0.09468(16) 0.22986(14) 0.0283(4) Uani 1 1 d . . . . .
C13 C 0.2673(2) 0.04980(16) 0.25366(15) 0.0297(4) Uani 1 1 d . . . . .
C14 C 0.1625(2) 0.07503(18) 0.34354(16) 0.0372(5) Uani 1 1 d . . . . .
H14 H 0.1772 0.1180 0.3914 0.045 Uiso 1 1 calc R U . . .
C15 C 0.0379(3) 0.0377(2) 0.36292(19) 0.0470(6) Uani 1 1 d . . . . .
H15 H -0.0329 0.0554 0.4240 0.056 Uiso 1 1 calc R U . . .
C16 C 0.0155(3) -0.0250(2) 0.2943(2) 0.0509(7) Uani 1 1 d . . . . .
H16 H -0.0710 -0.0499 0.3078 0.061 Uiso 1 1 calc R U . . .
C17 C 0.1192(3) -0.0516(2) 0.2058(2) 0.0480(6) Uani 1 1 d . . . . .
H17 H 0.1040 -0.0950 0.1586 0.058 Uiso 1 1 calc R U . . .
C18 C 0.2455(3) -0.01501(18) 0.18575(17) 0.0368(5) Uani 1 1 d . . . . .
H18 H 0.3172 -0.0344 0.1253 0.044 Uiso 1 1 calc R U . . .
C19 C 0.6929(3) -0.03233(17) 0.10989(17) 0.0373(5) Uani 1 1 d . . . . .
H19A H 0.6609 -0.0842 0.0787 0.056 Uiso 1 1 calc R U . . .
H19B H 0.7184 -0.0622 0.1776 0.056 Uiso 1 1 calc R U . . .
H19C H 0.7842 -0.0215 0.0675 0.056 Uiso 1 1 calc R U . . .
C20 C 0.6500(2) 0.46298(16) 0.26630(14) 0.0298(4) Uani 1 1 d . . . . .
C21 C 0.5406(3) 0.54962(18) 0.12961(16) 0.0423(6) Uani 1 1 d . . . . .
H21 H 0.4804 0.5533 0.0780 0.051 Uiso 1 1 calc R U . . .
C22 C 0.6019(3) 0.6311(2) 0.12955(18) 0.0522(7) Uani 1 1 d . . . . .
H22 H 0.5859 0.6909 0.0799 0.063 Uiso 1 1 calc R U . . .
C23 C 0.6878(4) 0.6213(2) 0.20543(19) 0.0558(7) Uani 1 1 d . . . . .
H23 H 0.7301 0.6776 0.2088 0.067 Uiso 1 1 calc R U . . .
C24 C 0.7831(2) 0.24813(15) 0.13699(15) 0.0283(4) Uani 1 1 d . . . . .
C25 C 0.7518(3) 0.26562(17) 0.03720(15) 0.0350(5) Uani 1 1 d . . . . .
H25 H 0.6548 0.2664 0.0234 0.042 Uiso 1 1 calc R U . . .
C26 C 0.8608(3) 0.28194(19) -0.04200(17) 0.0435(6) Uani 1 1 d . . . . .
H26 H 0.8381 0.2939 -0.1097 0.052 Uiso 1 1 calc R U . . .
C27 C 1.0026(3) 0.2808(2) -0.02252(18) 0.0469(6) Uani 1 1 d . . . . .
H27 H 1.0772 0.2921 -0.0768 0.056 Uiso 1 1 calc R U . . .
C28 C 1.0355(3) 0.26312(19) 0.07561(19) 0.0434(6) Uani 1 1 d . . . . .
H28 H 1.1333 0.2614 0.0889 0.052 Uiso 1 1 calc R U . . .
C29 C 0.9261(2) 0.24783(17) 0.15503(16) 0.0342(5) Uani 1 1 d . . . . .
H29 H 0.9490 0.2370 0.2226 0.041 Uiso 1 1 calc R U . . .
C30 C 0.7500(3) 0.51245(17) 0.65030(16) 0.0347(5) Uani 1 1 d . . . . .
C31 C 0.8191(4) 0.5515(2) 0.7988(2) 0.0593(8) Uani 1 1 d . . . . .
H31A H 0.8990 0.5793 0.7602 0.089 Uiso 1 1 calc R U . . .
H31B H 0.8523 0.5155 0.8632 0.089 Uiso 1 1 calc R U . . .
H31C H 0.7217 0.6132 0.8124 0.089 Uiso 1 1 calc R U . . .
H11 H 0.406(3) 0.1803(18) 0.3520(18) 0.039(6) Uiso 1 1 d . . . . .
H32B H 0.644(4) 0.734(3) 0.377(3) 0.103(13) Uiso 1 1 d . . . . .
H32A H 0.688(5) 0.732(4) 0.491(4) 0.142(17) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C32 1.773(6) . ?
Cl1' C32 1.699(9) . ?
Cl2 C32 1.733(3) . ?
C32 H32B 0.97(4) . ?
C32 H32A 0.98(5) . ?
P1 O1 1.4842(14) . ?
P1 C19 1.793(2) . ?
P1 C12 1.809(2) . ?
P1 C10 1.8246(19) . ?
P1 C11 2.295(2) . ?
O2 C30 1.205(3) . ?
O3 C30 1.342(2) . ?
O3 C31 1.440(3) . ?
N1 C8 1.409(2) . ?
N1 C20 1.409(2) . ?
N1 C1 1.409(2) . ?
N2 C20 1.325(3) . ?
N2 C23 1.342(3) . ?
N3 C20 1.323(3) . ?
N3 C21 1.334(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.407(3) . ?
C2 C3 1.392(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.403(3) . ?
C3 C30 1.487(3) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.422(3) . ?
C7 C8 1.360(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.474(3) . ?
C9 C10 1.350(3) . ?
C9 C24 1.481(3) . ?
C10 C11 1.453(3) . ?
C11 C12 1.357(3) . ?
C11 H11 0.98(2) . ?
C12 C13 1.456(3) . ?
C13 C18 1.388(3) . ?
C13 C14 1.400(3) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C22 1.363(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.369(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C29 1.393(3) . ?
C24 C25 1.394(3) . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.385(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.378(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(3) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 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
Cl1' C32 Cl2 112.4(3) . . ?
Cl2 C32 Cl1 111.0(2) . . ?
Cl1' C32 H32B 117(2) . . ?
Cl2 C32 H32B 102(2) . . ?
Cl1 C32 H32B 104(2) . . ?
Cl1' C32 H32A 102(3) . . ?
Cl2 C32 H32A 108(3) . . ?
Cl1 C32 H32A 116(3) . . ?
H32B C32 H32A 115(4) . . ?
O1 P1 C19 112.98(9) . . ?
O1 P1 C12 119.98(9) . . ?
C19 P1 C12 111.53(10) . . ?
O1 P1 C10 122.17(9) . . ?
C19 P1 C10 109.47(10) . . ?
C12 P1 C10 75.48(9) . . ?
O1 P1 C11 131.27(8) . . ?
C19 P1 C11 115.72(9) . . ?
C12 P1 C11 36.24(8) . . ?
C10 P1 C11 39.25(8) . . ?
C30 O3 C31 115.22(17) . . ?
C8 N1 C20 124.72(16) . . ?
C8 N1 C1 107.94(15) . . ?
C20 N1 C1 126.29(16) . . ?
C20 N2 C23 114.3(2) . . ?
C20 N3 C21 115.29(19) . . ?
C2 C1 C6 122.03(18) . . ?
C2 C1 N1 130.82(18) . . ?
C6 C1 N1 107.15(16) . . ?
C1 C2 C3 117.38(18) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C2 C3 C4 121.36(18) . . ?
C2 C3 C30 117.03(18) . . ?
C4 C3 C30 121.60(18) . . ?
C5 C4 C3 120.84(18) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.96(18) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.41(18) . . ?
C5 C6 C7 133.00(18) . . ?
C1 C6 C7 107.56(16) . . ?
C8 C7 C6 108.49(17) . . ?
C8 C7 H7 125.8 . . ?
C6 C7 H7 125.8 . . ?
C7 C8 N1 108.84(16) . . ?
C7 C8 C9 127.05(17) . . ?
N1 C8 C9 123.62(17) . . ?
C10 C9 C8 118.28(17) . . ?
C10 C9 C24 122.61(17) . . ?
C8 C9 C24 118.94(16) . . ?
C9 C10 C11 132.72(18) . . ?
C9 C10 P1 139.11(15) . . ?
C11 C10 P1 88.12(13) . . ?
C12 C11 C10 104.60(17) . . ?
C12 C11 P1 51.98(11) . . ?
C10 C11 P1 52.63(10) . . ?
C12 C11 H11 129.0(14) . . ?
C10 C11 H11 126.4(14) . . ?
P1 C11 H11 179.0(14) . . ?
C11 C12 C13 132.72(19) . . ?
C11 C12 P1 91.77(14) . . ?
C13 C12 P1 135.48(15) . . ?
C18 C13 C14 118.9(2) . . ?
C18 C13 C12 120.54(18) . . ?
C14 C13 C12 120.48(19) . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.3(2) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
P1 C19 H19A 109.5 . . ?
P1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
P1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 N2 127.68(19) . . ?
N3 C20 N1 115.66(17) . . ?
N2 C20 N1 116.66(17) . . ?
N3 C21 C22 123.2(2) . . ?
N3 C21 H21 118.4 . . ?
C22 C21 H21 118.4 . . ?
C21 C22 C23 115.8(2) . . ?
C21 C22 H22 122.1 . . ?
C23 C22 H22 122.1 . . ?
N2 C23 C22 123.6(2) . . ?
N2 C23 H23 118.2 . . ?
C22 C23 H23 118.2 . . ?
C29 C24 C25 118.39(19) . . ?
C29 C24 C9 120.77(17) . . ?
C25 C24 C9 120.83(18) . . ?
C26 C25 C24 120.7(2) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C27 C26 C25 120.0(2) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C28 C27 C26 120.0(2) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 120.1(2) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C24 120.8(2) . . ?
C28 C29 H29 119.6 . . ?
C24 C29 H29 119.6 . . ?
O2 C30 O3 122.62(19) . . ?
O2 C30 C3 124.67(19) . . ?
O3 C30 C3 112.70(18) . . ?
O3 C31 H31A 109.5 . . ?
O3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
C8 N1 C1 C2 179.0(2) . . . . ?
C20 N1 C1 C2 -12.4(3) . . . . ?
C8 N1 C1 C6 -1.3(2) . . . . ?
C20 N1 C1 C6 167.32(18) . . . . ?
C6 C1 C2 C3 1.6(3) . . . . ?
N1 C1 C2 C3 -178.77(19) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C1 C2 C3 C30 177.64(18) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C30 C3 C4 C5 -178.59(19) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 177.5(2) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
N1 C1 C6 C5 179.39(17) . . . . ?
C2 C1 C6 C7 -179.11(18) . . . . ?
N1 C1 C6 C7 1.2(2) . . . . ?
C5 C6 C7 C8 -178.5(2) . . . . ?
C1 C6 C7 C8 -0.6(2) . . . . ?
C6 C7 C8 N1 -0.2(2) . . . . ?
C6 C7 C8 C9 171.88(18) . . . . ?
C20 N1 C8 C7 -167.90(18) . . . . ?
C1 N1 C8 C7 1.0(2) . . . . ?
C20 N1 C8 C9 19.7(3) . . . . ?
C1 N1 C8 C9 -171.46(17) . . . . ?
C7 C8 C9 C10 47.6(3) . . . . ?
N1 C8 C9 C10 -141.43(19) . . . . ?
C7 C8 C9 C24 -127.7(2) . . . . ?
N1 C8 C9 C24 43.3(3) . . . . ?
C8 C9 C10 C11 7.3(3) . . . . ?
C24 C9 C10 C11 -177.65(19) . . . . ?
C8 C9 C10 P1 -169.21(17) . . . . ?
C24 C9 C10 P1 5.8(3) . . . . ?
O1 P1 C10 C9 -65.1(3) . . . . ?
C19 P1 C10 C9 70.3(2) . . . . ?
C12 P1 C10 C9 178.4(2) . . . . ?
C11 P1 C10 C9 177.4(3) . . . . ?
O1 P1 C10 C11 117.50(13) . . . . ?
C19 P1 C10 C11 -107.15(13) . . . . ?
C12 P1 C10 C11 0.95(12) . . . . ?
C9 C10 C11 C12 -179.0(2) . . . . ?
P1 C10 C11 C12 -1.26(15) . . . . ?
C9 C10 C11 P1 -177.7(3) . . . . ?
C10 C11 C12 C13 -177.0(2) . . . . ?
P1 C11 C12 C13 -178.2(3) . . . . ?
C10 C11 C12 P1 1.27(16) . . . . ?
O1 P1 C12 C11 -120.06(13) . . . . ?
C19 P1 C12 C11 104.53(14) . . . . ?
C10 P1 C12 C11 -1.01(12) . . . . ?
O1 P1 C12 C13 58.1(2) . . . . ?
C19 P1 C12 C13 -77.3(2) . . . . ?
C10 P1 C12 C13 177.1(2) . . . . ?
C11 P1 C12 C13 178.2(3) . . . . ?
C11 C12 C13 C18 -176.8(2) . . . . ?
P1 C12 C13 C18 5.7(3) . . . . ?
C11 C12 C13 C14 5.8(3) . . . . ?
P1 C12 C13 C14 -171.71(17) . . . . ?
C18 C13 C14 C15 -1.3(3) . . . . ?
C12 C13 C14 C15 176.1(2) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C14 C13 C18 C17 1.6(3) . . . . ?
C12 C13 C18 C17 -175.8(2) . . . . ?
C16 C17 C18 C13 -0.9(3) . . . . ?
C21 N3 C20 N2 2.6(3) . . . . ?
C21 N3 C20 N1 -178.01(18) . . . . ?
C23 N2 C20 N3 -1.0(3) . . . . ?
C23 N2 C20 N1 179.6(2) . . . . ?
C8 N1 C20 N3 22.3(3) . . . . ?
C1 N1 C20 N3 -144.49(19) . . . . ?
C8 N1 C20 N2 -158.23(19) . . . . ?
C1 N1 C20 N2 34.9(3) . . . . ?
C20 N3 C21 C22 -2.1(3) . . . . ?
N3 C21 C22 C23 0.2(4) . . . . ?
C20 N2 C23 C22 -1.2(4) . . . . ?
C21 C22 C23 N2 1.6(4) . . . . ?
C10 C9 C24 C29 -145.1(2) . . . . ?
C8 C9 C24 C29 29.9(3) . . . . ?
C10 C9 C24 C25 36.1(3) . . . . ?
C8 C9 C24 C25 -148.90(19) . . . . ?
C29 C24 C25 C26 0.2(3) . . . . ?
C9 C24 C25 C26 179.01(19) . . . . ?
C24 C25 C26 C27 0.1(3) . . . . ?
C25 C26 C27 C28 0.2(4) . . . . ?
C26 C27 C28 C29 -0.8(4) . . . . ?
C27 C28 C29 C24 1.1(3) . . . . ?
C25 C24 C29 C28 -0.8(3) . . . . ?
C9 C24 C29 C28 -179.63(19) . . . . ?
C31 O3 C30 O2 2.5(3) . . . . ?
C31 O3 C30 C3 -178.2(2) . . . . ?
C2 C3 C30 O2 13.3(3) . . . . ?
C4 C3 C30 O2 -167.8(2) . . . . ?
C2 C3 C30 O3 -166.00(18) . . . . ?
C4 C3 C30 O3 12.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C32 H32A O2 0.98(5) 2.21(5) 3.127(4) 154(4) .
C11 H11 O2 0.98(2) 2.66(2) 3.260(3) 120.0(16) 2_666
C23 H23 Cl1 0.95 2.84 3.552(4) 132.7 .
C22 H22 O1 0.95 2.32 3.264(3) 170.3 2_665
C19 H19A O1 0.98 2.47 3.398(3) 158.1 2_655
C2 H2 N2 0.95 2.46 2.992(3) 115.4 .

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

