# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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. 
# 
#######################################################################

data_220627f
_database_code_depnum_ccdc_archive 'CCDC 2249896'
loop_
_audit_author_name
_audit_author_address
'guoying zhang'
;Institute of Coal Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-03-20 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 N2'
_chemical_formula_weight         326.43

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8961(11)
_cell_length_b                   18.4187(17)
_cell_length_c                   9.4952(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.962(5)
_cell_angle_gamma                90.00
_cell_volume                     1767.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1737
_cell_measurement_theta_min      2.313
_cell_measurement_theta_max      23.654

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9677
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8212
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_av_sigmaI/netI    0.1370
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3088
_reflns_number_gt                1605
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0977P)²+0.1507P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3088
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1697
_refine_ls_R_factor_gt           0.0901
_refine_ls_wR_factor_ref         0.2449
_refine_ls_wR_factor_gt          0.2066
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3476(3) 0.67451(16) 0.3456(3) 0.0378(8) Uani 1 1 d . . .
N2 N 0.4568(3) 0.66059(16) 0.3164(3) 0.0364(8) Uani 1 1 d . . .
C1 C 0.2552(4) 0.7287(2) 0.2656(4) 0.0423(11) Uani 1 1 d . . .
H1A H 0.3036 0.7689 0.2451 0.051 Uiso 1 1 calc R . .
H1B H 0.2120 0.7467 0.3313 0.051 Uiso 1 1 calc R . .
C2 C 0.1534(4) 0.7059(2) 0.1226(4) 0.0378(10) Uani 1 1 d . . .
H2 H 0.0860 0.7388 0.0744 0.045 Uiso 1 1 calc R . .
C3 C 0.1489(4) 0.6440(2) 0.0572(4) 0.0384(10) Uani 1 1 d . . .
H3 H 0.2183 0.6124 0.1060 0.046 Uiso 1 1 calc R . .
C4 C 0.0506(4) 0.6177(2) -0.0809(4) 0.0375(10) Uani 1 1 d . . .
C5 C 0.0480(4) 0.5471(2) -0.1198(5) 0.0460(11) Uani 1 1 d . . .
H5 H 0.1148 0.5167 -0.0584 0.055 Uiso 1 1 calc R . .
C6 C -0.0470(5) 0.5183(3) -0.2437(5) 0.0538(12) Uani 1 1 d . . .
H6 H -0.0459 0.4692 -0.2656 0.065 Uiso 1 1 calc R . .
C7 C -0.1435(5) 0.5617(3) -0.3352(5) 0.0612(13) Uani 1 1 d . . .
H7 H -0.2101 0.5426 -0.4203 0.073 Uiso 1 1 calc R . .
C8 C -0.1430(5) 0.6330(3) -0.3025(5) 0.0667(14) Uani 1 1 d . . .
H8 H -0.2086 0.6633 -0.3661 0.080 Uiso 1 1 calc R . .
C9 C -0.0473(4) 0.6604(2) -0.1775(5) 0.0507(11) Uani 1 1 d . . .
H9 H -0.0482 0.7097 -0.1567 0.061 Uiso 1 1 calc R . .
C10 C 0.3352(4) 0.63628(19) 0.4645(4) 0.0356(10) Uani 1 1 d . . .
C11 C 0.4403(4) 0.6009(2) 0.5680(5) 0.0462(11) Uani 1 1 d . . .
H11 H 0.5213 0.6014 0.5562 0.055 Uiso 1 1 calc R . .
C12 C 0.4300(5) 0.5652(2) 0.6877(5) 0.0513(11) Uani 1 1 d . . .
C13 C 0.3096(5) 0.5642(2) 0.7034(5) 0.0588(13) Uani 1 1 d . . .
H13 H 0.3005 0.5405 0.7855 0.071 Uiso 1 1 calc R . .
C14 C 0.2053(5) 0.5974(2) 0.5999(6) 0.0582(13) Uani 1 1 d . . .
H14 H 0.1239 0.5957 0.6107 0.070 Uiso 1 1 calc R . .
C15 C 0.2149(4) 0.6334(2) 0.4801(5) 0.0462(11) Uani 1 1 d . . .
H15 H 0.1410 0.6558 0.4094 0.055 Uiso 1 1 calc R . .
C16 C 0.5451(5) 0.5270(3) 0.7974(5) 0.0752(16) Uani 1 1 d . . .
H16A H 0.6193 0.5317 0.7668 0.113 Uiso 1 1 calc R . .
H16B H 0.5241 0.4765 0.8003 0.113 Uiso 1 1 calc R . .
H16C H 0.5667 0.5479 0.8964 0.113 Uiso 1 1 calc R . .
C17 C 0.4733(4) 0.6898(2) 0.2049(4) 0.0388(10) Uani 1 1 d . . .
H17 H 0.4091 0.7204 0.1399 0.047 Uiso 1 1 calc R . .
C18 C 0.5939(4) 0.6751(2) 0.1797(4) 0.0363(9) Uani 1 1 d . . .
C19 C 0.6936(4) 0.6362(3) 0.2781(5) 0.0594(13) Uani 1 1 d . . .
H19 H 0.6857 0.6179 0.3656 0.071 Uiso 1 1 calc R . .
C20 C 0.8060(5) 0.6233(3) 0.2511(6) 0.0723(15) Uani 1 1 d . . .
H20 H 0.8741 0.5964 0.3204 0.087 Uiso 1 1 calc R . .
C21 C 0.8191(5) 0.6490(3) 0.1262(6) 0.0629(14) Uani 1 1 d . . .
H21 H 0.8965 0.6405 0.1089 0.075 Uiso 1 1 calc R . .
C22 C 0.7211(5) 0.6869(3) 0.0265(6) 0.0692(15) Uani 1 1 d . . .
H22 H 0.7291 0.7041 -0.0617 0.083 Uiso 1 1 calc R . .
C23 C 0.6083(4) 0.7005(2) 0.0536(5) 0.0585(13) Uani 1 1 d . . .
H23 H 0.5407 0.7276 -0.0160 0.070 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.343(4) . ?
N1 C10 1.379(4) . ?
N1 C1 1.420(5) . ?
N2 C17 1.259(4) . ?
C1 C2 1.457(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.291(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.431(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.351(5) . ?
C4 C9 1.366(5) . ?
C5 C6 1.351(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.347(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.348(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.351(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.364(5) . ?
C10 C15 1.375(5) . ?
C11 C12 1.354(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(6) . ?
C12 C16 1.474(6) . ?
C13 C14 1.340(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.354(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.446(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.344(5) . ?
C18 C23 1.348(5) . ?
C19 C20 1.363(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.334(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.330(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(6) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

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
N2 N1 C10 115.9(3) . . ?
N2 N1 C1 122.0(3) . . ?
C10 N1 C1 122.0(3) . . ?
C17 N2 N1 120.5(3) . . ?
N1 C1 C2 115.8(3) . . ?
N1 C1 H1A 108.3 . . ?
C2 C1 H1A 108.3 . . ?
N1 C1 H1B 108.3 . . ?
C2 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C3 C2 C1 125.6(4) . . ?
C3 C2 H2 117.2 . . ?
C1 C2 H2 117.2 . . ?
C2 C3 C4 128.3(4) . . ?
C2 C3 H3 115.8 . . ?
C4 C3 H3 115.8 . . ?
C5 C4 C9 116.1(4) . . ?
C5 C4 C3 120.5(4) . . ?
C9 C4 C3 123.3(4) . . ?
C4 C5 C6 123.1(4) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C7 C6 C5 119.2(4) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 119.6(5) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.1(4) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C4 121.8(4) . . ?
C8 C9 H9 119.1 . . ?
C4 C9 H9 119.1 . . ?
C11 C10 C15 118.7(4) . . ?
C11 C10 N1 121.4(3) . . ?
C15 C10 N1 119.9(4) . . ?
C12 C11 C10 121.8(4) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 118.6(4) . . ?
C11 C12 C16 120.6(4) . . ?
C13 C12 C16 120.8(4) . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 121.9(4) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C10 119.1(4) . . ?
C14 C15 H15 120.4 . . ?
C10 C15 H15 120.4 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C18 118.9(3) . . ?
N2 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C19 C18 C23 118.1(4) . . ?
C19 C18 C17 122.2(4) . . ?
C23 C18 C17 119.8(4) . . ?
C18 C19 C20 120.8(4) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 120.6(5) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 119.6(4) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.1(4) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 120.9(4) . . ?
C18 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?

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
C10 N1 N2 C17 176.1(3) . . . . ?
C1 N1 N2 C17 -8.0(5) . . . . ?
N2 N1 C1 C2 86.0(4) . . . . ?
C10 N1 C1 C2 -98.4(4) . . . . ?
N1 C1 C2 C3 -7.3(6) . . . . ?
C1 C2 C3 C4 178.5(3) . . . . ?
C2 C3 C4 C5 -168.1(4) . . . . ?
C2 C3 C4 C9 9.5(6) . . . . ?
C9 C4 C5 C6 -2.0(6) . . . . ?
C3 C4 C5 C6 175.8(4) . . . . ?
C4 C5 C6 C7 0.9(6) . . . . ?
C5 C6 C7 C8 0.6(7) . . . . ?
C6 C7 C8 C9 -1.0(7) . . . . ?
C7 C8 C9 C4 -0.2(7) . . . . ?
C5 C4 C9 C8 1.6(6) . . . . ?
C3 C4 C9 C8 -176.1(4) . . . . ?
N2 N1 C10 C11 15.6(5) . . . . ?
C1 N1 C10 C11 -160.3(4) . . . . ?
N2 N1 C10 C15 -164.4(3) . . . . ?
C1 N1 C10 C15 19.7(5) . . . . ?
C15 C10 C11 C12 -2.0(6) . . . . ?
N1 C10 C11 C12 177.9(4) . . . . ?
C10 C11 C12 C13 0.6(6) . . . . ?
C10 C11 C12 C16 179.6(4) . . . . ?
C11 C12 C13 C14 0.9(7) . . . . ?
C16 C12 C13 C14 -178.0(4) . . . . ?
C12 C13 C14 C15 -1.0(7) . . . . ?
C13 C14 C15 C10 -0.4(6) . . . . ?
C11 C10 C15 C14 1.9(6) . . . . ?
N1 C10 C15 C14 -178.1(3) . . . . ?
N1 N2 C17 C18 178.3(3) . . . . ?
N2 C17 C18 C19 -5.7(6) . . . . ?
N2 C17 C18 C23 174.0(4) . . . . ?
C23 C18 C19 C20 0.4(7) . . . . ?
C17 C18 C19 C20 -180.0(4) . . . . ?
C18 C19 C20 C21 -0.1(8) . . . . ?
C19 C20 C21 C22 -0.7(8) . . . . ?
C20 C21 C22 C23 1.2(8) . . . . ?
C19 C18 C23 C22 0.2(7) . . . . ?
C17 C18 C23 C22 -179.5(4) . . . . ?
C21 C22 C23 C18 -1.0(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_220521h
_database_code_depnum_ccdc_archive 'CCDC 2249897'
loop_
_audit_author_name
_audit_author_address
'guoying zhang'
;Institute of Coal Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-03-20 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 N2'
_chemical_formula_weight         312.40

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0309(9)
_cell_length_b                   19.6236(18)
_cell_length_c                   9.0074(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.371(4)
_cell_angle_gamma                90.00
_cell_volume                     1717.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1355
_cell_measurement_theta_min      2.543
_cell_measurement_theta_max      20.328

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      \"i1/4\"Y
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9804
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8289
_diffrn_reflns_av_R_equivalents  0.1191
_diffrn_reflns_av_sigmaI/netI    0.1180
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3020
_reflns_number_gt                1268
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0939P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3020
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1937
_refine_ls_R_factor_gt           0.0881
_refine_ls_wR_factor_ref         0.2396
_refine_ls_wR_factor_gt          0.1964
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3124(4) 0.16306(15) 0.6136(4) 0.0635(9) Uani 1 1 d . . .
N2 N 0.3950(4) 0.10878(15) 0.6706(4) 0.0633(9) Uani 1 1 d . . .
C1 C 0.4959(5) 0.09467(19) 0.6167(5) 0.0628(11) Uani 1 1 d . . .
H1 H 0.5144 0.1207 0.5379 0.075 Uiso 1 1 calc R . .
C2 C 0.5839(5) 0.03671(19) 0.6797(5) 0.0624(11) Uani 1 1 d . . .
C3 C 0.6965(5) 0.0248(2) 0.6263(6) 0.0875(14) Uani 1 1 d . . .
H3 H 0.7155 0.0526 0.5504 0.105 Uiso 1 1 calc R . .
C4 C 0.7827(6) -0.0283(3) 0.6844(8) 0.1128(19) Uani 1 1 d . . .
H4 H 0.8601 -0.0365 0.6477 0.135 Uiso 1 1 calc R . .
C5 C 0.7559(6) -0.0684(3) 0.7938(8) 0.1033(19) Uani 1 1 d . . .
H5 H 0.8166 -0.1034 0.8345 0.124 Uiso 1 1 calc R . .
C6 C 0.6422(6) -0.0590(2) 0.8458(6) 0.0957(17) Uani 1 1 d . . .
H6 H 0.6227 -0.0879 0.9195 0.115 Uiso 1 1 calc R . .
C7 C 0.5555(5) -0.0058(2) 0.7877(5) 0.0760(13) Uani 1 1 d . . .
H7 H 0.4767 0.0012 0.8224 0.091 Uiso 1 1 calc R . .
C8 C 0.1966(5) 0.16891(18) 0.6678(5) 0.0604(11) Uani 1 1 d . . .
C9 C 0.1137(5) 0.2277(2) 0.6362(5) 0.0767(13) Uani 1 1 d . . .
H9 H 0.1379 0.2630 0.5792 0.092 Uiso 1 1 calc R . .
C10 C -0.0005(6) 0.2329(3) 0.6884(6) 0.0895(16) Uani 1 1 d . . .
H10 H -0.0528 0.2725 0.6678 0.107 Uiso 1 1 calc R . .
C11 C -0.0419(6) 0.1832(3) 0.7688(7) 0.0990(17) Uani 1 1 d . . .
H11 H -0.1223 0.1875 0.8018 0.119 Uiso 1 1 calc R . .
C12 C 0.0389(6) 0.1253(3) 0.8012(6) 0.0935(15) Uani 1 1 d . . .
H12 H 0.0138 0.0905 0.8589 0.112 Uiso 1 1 calc R . .
C13 C 0.1540(5) 0.1187(2) 0.7498(5) 0.0752(13) Uani 1 1 d . . .
H13 H 0.2054 0.0789 0.7710 0.090 Uiso 1 1 calc R . .
C14 C 0.3328(5) 0.20116(19) 0.4824(5) 0.0713(12) Uani 1 1 d . . .
H14A H 0.2452 0.2209 0.4295 0.086 Uiso 1 1 calc R . .
H14B H 0.3591 0.1692 0.4125 0.086 Uiso 1 1 calc R . .
C15 C 0.4370(5) 0.25680(19) 0.5150(5) 0.0690(12) Uani 1 1 d . . .
H15 H 0.4336 0.2885 0.4373 0.083 Uiso 1 1 calc R . .
C16 C 0.5313(5) 0.26554(19) 0.6395(5) 0.0666(12) Uani 1 1 d . . .
H16 H 0.5316 0.2353 0.7190 0.080 Uiso 1 1 calc R . .
C17 C 0.6385(4) 0.31839(19) 0.6691(5) 0.0594(11) Uani 1 1 d . . .
C18 C 0.6609(5) 0.3613(2) 0.5587(5) 0.0781(13) Uani 1 1 d . . .
H18 H 0.6070 0.3574 0.4590 0.094 Uiso 1 1 calc R . .
C19 C 0.7600(6) 0.4092(3) 0.5921(7) 0.0969(16) Uani 1 1 d . . .
H19 H 0.7702 0.4393 0.5159 0.116 Uiso 1 1 calc R . .
C20 C 0.8443(5) 0.4144(2) 0.7331(8) 0.0947(17) Uani 1 1 d . . .
H20 H 0.9143 0.4468 0.7536 0.114 Uiso 1 1 calc R . .
C21 C 0.8262(5) 0.3717(2) 0.8457(6) 0.0863(14) Uani 1 1 d . . .
H21 H 0.8822 0.3754 0.9445 0.104 Uiso 1 1 calc R . .
C22 C 0.7247(5) 0.3233(2) 0.8125(5) 0.0706(12) Uani 1 1 d . . .
H22 H 0.7143 0.2932 0.8886 0.085 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.369(4) . ?
N1 C8 1.372(5) . ?
N1 C14 1.455(5) . ?
N2 C1 1.257(4) . ?
C1 C2 1.465(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.353(6) . ?
C2 C7 1.365(5) . ?
C3 C4 1.373(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.339(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.349(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.362(5) . ?
C8 C9 1.410(5) . ?
C9 C10 1.345(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.340(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.352(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.490(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.286(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.470(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(5) . ?
C17 C22 1.367(6) . ?
C18 C19 1.347(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.344(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.362(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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
N2 N1 C8 114.7(3) . . ?
N2 N1 C14 120.7(3) . . ?
C8 N1 C14 123.2(3) . . ?
C1 N2 N1 119.8(4) . . ?
N2 C1 C2 119.2(4) . . ?
N2 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C3 C2 C7 119.3(4) . . ?
C3 C2 C1 118.2(4) . . ?
C7 C2 C1 122.5(4) . . ?
C2 C3 C4 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 118.7(5) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 120.7(5) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C13 C8 N1 122.7(4) . . ?
C13 C8 C9 116.9(4) . . ?
N1 C8 C9 120.4(4) . . ?
C10 C9 C8 120.1(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 122.6(5) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C10 C11 C12 117.8(5) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C8 121.7(4) . . ?
C12 C13 H13 119.1 . . ?
C8 C13 H13 119.1 . . ?
N1 C14 C15 116.8(3) . . ?
N1 C14 H14A 108.1 . . ?
C15 C14 H14A 108.1 . . ?
N1 C14 H14B 108.1 . . ?
C15 C14 H14B 108.1 . . ?
H14A C14 H14B 107.3 . . ?
C16 C15 C14 126.7(4) . . ?
C16 C15 H15 116.7 . . ?
C14 C15 H15 116.7 . . ?
C15 C16 C17 126.8(4) . . ?
C15 C16 H16 116.6 . . ?
C17 C16 H16 116.6 . . ?
C18 C17 C22 117.7(4) . . ?
C18 C17 C16 123.3(4) . . ?
C22 C17 C16 118.9(4) . . ?
C19 C18 C17 121.0(5) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 121.4(5) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 119.2(5) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C20 C21 C22 119.5(5) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C17 C22 C21 121.1(4) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?

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 N2 C1 172.7(4) . . . . ?
C14 N1 N2 C1 5.3(5) . . . . ?
N1 N2 C1 C2 179.5(3) . . . . ?
N2 C1 C2 C3 -176.2(4) . . . . ?
N2 C1 C2 C7 4.7(6) . . . . ?
C7 C2 C3 C4 -2.0(7) . . . . ?
C1 C2 C3 C4 178.9(4) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C3 C4 C5 C6 2.0(8) . . . . ?
C4 C5 C6 C7 -2.0(8) . . . . ?
C3 C2 C7 C6 2.1(6) . . . . ?
C1 C2 C7 C6 -178.9(4) . . . . ?
C5 C6 C7 C2 -0.1(7) . . . . ?
N2 N1 C8 C13 -11.1(5) . . . . ?
C14 N1 C8 C13 155.8(4) . . . . ?
N2 N1 C8 C9 170.6(3) . . . . ?
C14 N1 C8 C9 -22.4(6) . . . . ?
C13 C8 C9 C10 1.0(6) . . . . ?
N1 C8 C9 C10 179.3(4) . . . . ?
C8 C9 C10 C11 -1.2(8) . . . . ?
C9 C10 C11 C12 1.4(8) . . . . ?
C10 C11 C12 C13 -1.6(8) . . . . ?
C11 C12 C13 C8 1.5(7) . . . . ?
N1 C8 C13 C12 -179.5(4) . . . . ?
C9 C8 C13 C12 -1.2(6) . . . . ?
N2 N1 C14 C15 -85.3(4) . . . . ?
C8 N1 C14 C15 108.5(4) . . . . ?
N1 C14 C15 C16 16.3(6) . . . . ?
C14 C15 C16 C17 176.7(4) . . . . ?
C15 C16 C17 C18 -7.8(7) . . . . ?
C15 C16 C17 C22 175.3(4) . . . . ?
C22 C17 C18 C19 -3.5(6) . . . . ?
C16 C17 C18 C19 179.6(4) . . . . ?
C17 C18 C19 C20 3.2(7) . . . . ?
C18 C19 C20 C21 -2.2(8) . . . . ?
C19 C20 C21 C22 1.6(7) . . . . ?
C18 C17 C22 C21 2.9(6) . . . . ?
C16 C17 C22 C21 -180.0(4) . . . . ?
C20 C21 C22 C17 -2.0(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_230101b
_database_code_depnum_ccdc_archive 'CCDC 2249898'
loop_
_audit_author_name
_audit_author_address
'guoying zhang'
;Institute of Coal Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-03-20 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 F N2'
_chemical_formula_weight         330.39

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4540(9)
_cell_length_b                   20.0412(18)
_cell_length_c                   9.0834(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.374(4)
_cell_angle_gamma                90.00
_cell_volume                     1825.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1634
_cell_measurement_theta_min      2.819
_cell_measurement_theta_max      25.558

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9030
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3187
_reflns_number_gt                1313
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0946P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3187
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1708
_refine_ls_R_factor_gt           0.0764
_refine_ls_wR_factor_ref         0.2275
_refine_ls_wR_factor_gt          0.1914
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9247(3) 0.45430(14) 0.2768(4) 0.1667(14) Uani 1 1 d . . .
N1 N 0.3003(4) 0.16366(15) 0.1163(4) 0.0879(10) Uani 1 1 d . . .
N2 N 0.3790(4) 0.11089(14) 0.1748(3) 0.0792(9) Uani 1 1 d . . .
C1 C 0.3163(4) 0.20016(19) -0.0190(5) 0.1041(14) Uani 1 1 d . . .
H1A H 0.2318 0.2211 -0.0703 0.125 Uiso 1 1 calc R . .
H1B H 0.3353 0.1679 -0.0896 0.125 Uiso 1 1 calc R . .
C2 C 0.4243(4) 0.2536(2) 0.0124(5) 0.1000(13) Uani 1 1 d . . .
H2 H 0.4225 0.2825 -0.0683 0.120 Uiso 1 1 calc R . .
C3 C 0.5183(4) 0.26345(19) 0.1384(5) 0.0992(14) Uani 1 1 d . . .
H3 H 0.5175 0.2353 0.2195 0.119 Uiso 1 1 calc R . .
C4 C 0.6272(4) 0.31383(17) 0.1704(4) 0.0783(11) Uani 1 1 d . . .
C5 C 0.6467(4) 0.3560(2) 0.0597(5) 0.0924(12) Uani 1 1 d . . .
H5 H 0.5916 0.3524 -0.0401 0.111 Uiso 1 1 calc R . .
C6 C 0.7454(5) 0.4032(2) 0.0929(6) 0.0992(13) Uani 1 1 d . . .
H6 H 0.7572 0.4317 0.0169 0.119 Uiso 1 1 calc R . .
C7 C 0.8251(4) 0.4076(2) 0.2377(7) 0.1008(14) Uani 1 1 d . . .
C8 C 0.8137(4) 0.3667(2) 0.3543(6) 0.0964(13) Uani 1 1 d . . .
H8 H 0.8703 0.3706 0.4533 0.116 Uiso 1 1 calc R . .
C9 C 0.7126(4) 0.31911(18) 0.3165(5) 0.0863(12) Uani 1 1 d . . .
H9 H 0.7025 0.2900 0.3921 0.104 Uiso 1 1 calc R . .
C10 C 0.1850(5) 0.17065(19) 0.1688(5) 0.0865(13) Uani 1 1 d . . .
C11 C 0.1441(5) 0.1213(2) 0.2506(5) 0.0984(14) Uani 1 1 d . . .
H11 H 0.1938 0.0822 0.2728 0.118 Uiso 1 1 calc R . .
C12 C 0.0321(5) 0.1278(2) 0.3005(6) 0.1147(15) Uani 1 1 d . . .
H12 H 0.0069 0.0931 0.3544 0.138 Uiso 1 1 calc R . .
C13 C -0.0440(5) 0.1862(3) 0.2708(6) 0.1283(18) Uani 1 1 d . . .
H13 H -0.1192 0.1914 0.3052 0.154 Uiso 1 1 calc R . .
C14 C -0.0044(6) 0.2347(3) 0.1905(7) 0.124(2) Uani 1 1 d . . .
H14 H -0.0552 0.2734 0.1682 0.149 Uiso 1 1 calc R . .
C15 C 0.1094(6) 0.2295(2) 0.1390(5) 0.1122(16) Uani 1 1 d . . .
H15 H 0.1345 0.2645 0.0859 0.135 Uiso 1 1 calc R . .
C16 C 0.4778(4) 0.09727(19) 0.1216(4) 0.0791(11) Uani 1 1 d . . .
H16 H 0.4939 0.1228 0.0432 0.095 Uiso 1 1 calc R . .
C17 C 0.5648(4) 0.04069(19) 0.1870(4) 0.0795(11) Uani 1 1 d . . .
C18 C 0.6789(5) 0.0312(3) 0.1415(5) 0.1029(13) Uani 1 1 d . . .
H18 H 0.6970 0.0592 0.0680 0.123 Uiso 1 1 calc R . .
C19 C 0.7656(5) -0.0193(3) 0.2045(7) 0.1246(17) Uani 1 1 d . . .
H19 H 0.8428 -0.0247 0.1740 0.150 Uiso 1 1 calc R . .
C20 C 0.7417(6) -0.0612(3) 0.3092(7) 0.1153(17) Uani 1 1 d . . .
H20 H 0.8020 -0.0949 0.3516 0.138 Uiso 1 1 calc R . .
C21 C 0.6268(5) -0.0535(2) 0.3530(5) 0.1035(14) Uani 1 1 d . . .
H21 H 0.6084 -0.0826 0.4241 0.124 Uiso 1 1 calc R . .
C22 C 0.5393(4) -0.0030(2) 0.2920(5) 0.0879(12) Uani 1 1 d . . .
H22 H 0.4618 0.0018 0.3220 0.105 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C7 1.371(4) . ?
N1 N2 1.353(4) . ?
N1 C10 1.422(5) . ?
N1 C1 1.480(5) . ?
N2 C16 1.286(4) . ?
C1 C2 1.523(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.297(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.488(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(5) . ?
C4 C9 1.379(5) . ?
C5 C6 1.370(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.347(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.370(6) . ?
C8 C9 1.393(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.376(6) . ?
C10 C15 1.403(5) . ?
C11 C12 1.376(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.399(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.348(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.400(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.470(5) . ?
C16 H16 0.9300 . ?
C17 C22 1.375(5) . ?
C17 C18 1.382(5) . ?
C18 C19 1.372(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.344(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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
N2 N1 C10 115.1(3) . . ?
N2 N1 C1 120.9(4) . . ?
C10 N1 C1 122.3(3) . . ?
C16 N2 N1 118.8(4) . . ?
N1 C1 C2 116.3(3) . . ?
N1 C1 H1A 108.2 . . ?
C2 C1 H1A 108.2 . . ?
N1 C1 H1B 108.2 . . ?
C2 C1 H1B 108.2 . . ?
H1A C1 H1B 107.4 . . ?
C3 C2 C1 127.6(4) . . ?
C3 C2 H2 116.2 . . ?
C1 C2 H2 116.2 . . ?
C2 C3 C4 128.6(4) . . ?
C2 C3 H3 115.7 . . ?
C4 C3 H3 115.7 . . ?
C5 C4 C9 117.9(4) . . ?
C5 C4 C3 122.6(4) . . ?
C9 C4 C3 119.5(4) . . ?
C6 C5 C4 121.5(4) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 C6 C5 118.7(4) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C8 123.5(4) . . ?
C6 C7 F1 120.8(5) . . ?
C8 C7 F1 115.7(5) . . ?
C7 C8 C9 116.3(4) . . ?
C7 C8 H8 121.8 . . ?
C9 C8 H8 121.8 . . ?
C4 C9 C8 122.0(4) . . ?
C4 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C11 C10 C15 117.7(5) . . ?
C11 C10 N1 122.1(4) . . ?
C15 C10 N1 120.2(5) . . ?
C12 C11 C10 122.2(4) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 C13 120.4(5) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 117.6(6) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C13 C14 C15 123.2(5) . . ?
C13 C14 H14 118.4 . . ?
C15 C14 H14 118.4 . . ?
C14 C15 C10 118.9(5) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?
N2 C16 C17 118.8(4) . . ?
N2 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C22 C17 C18 118.2(4) . . ?
C22 C17 C16 123.5(4) . . ?
C18 C17 C16 118.2(4) . . ?
C19 C18 C17 120.0(5) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 121.6(5) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 119.1(5) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C22 C21 C20 120.2(5) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 120.8(4) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?

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
C10 N1 N2 C16 173.1(3) . . . . ?
C1 N1 N2 C16 7.6(5) . . . . ?
N2 N1 C1 C2 -83.4(4) . . . . ?
C10 N1 C1 C2 112.1(4) . . . . ?
N1 C1 C2 C3 12.6(6) . . . . ?
C1 C2 C3 C4 177.9(4) . . . . ?
C2 C3 C4 C5 -4.3(7) . . . . ?
C2 C3 C4 C9 175.6(4) . . . . ?
C9 C4 C5 C6 -1.7(6) . . . . ?
C3 C4 C5 C6 178.2(3) . . . . ?
C4 C5 C6 C7 0.4(6) . . . . ?
C5 C6 C7 C8 0.6(6) . . . . ?
C5 C6 C7 F1 -179.6(3) . . . . ?
C6 C7 C8 C9 -0.3(6) . . . . ?
F1 C7 C8 C9 179.8(3) . . . . ?
C5 C4 C9 C8 2.0(6) . . . . ?
C3 C4 C9 C8 -177.9(3) . . . . ?
C7 C8 C9 C4 -1.0(5) . . . . ?
N2 N1 C10 C11 -11.1(5) . . . . ?
C1 N1 C10 C11 154.3(4) . . . . ?
N2 N1 C10 C15 168.3(3) . . . . ?
C1 N1 C10 C15 -26.3(5) . . . . ?
C15 C10 C11 C12 1.0(6) . . . . ?
N1 C10 C11 C12 -179.6(3) . . . . ?
C10 C11 C12 C13 -0.8(6) . . . . ?
C11 C12 C13 C14 0.9(7) . . . . ?
C12 C13 C14 C15 -1.2(7) . . . . ?
C13 C14 C15 C10 1.5(7) . . . . ?
C11 C10 C15 C14 -1.3(6) . . . . ?
N1 C10 C15 C14 179.3(4) . . . . ?
N1 N2 C16 C17 178.9(3) . . . . ?
N2 C16 C17 C22 6.7(5) . . . . ?
N2 C16 C17 C18 -172.8(3) . . . . ?
C22 C17 C18 C19 -2.2(6) . . . . ?
C16 C17 C18 C19 177.3(4) . . . . ?
C17 C18 C19 C20 1.0(7) . . . . ?
C18 C19 C20 C21 0.7(7) . . . . ?
C19 C20 C21 C22 -1.1(6) . . . . ?
C20 C21 C22 C17 -0.2(6) . . . . ?
C18 C17 C22 C21 1.8(5) . . . . ?
C16 C17 C22 C21 -177.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_220627b
_database_code_depnum_ccdc_archive 'CCDC 2249900'
loop_
_audit_author_name
_audit_author_address
'guoying zhang'
;Institute of Coal Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-03-20 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C49 H41 F3 O4 P2 Pd S'
_chemical_formula_weight         951.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/m

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.2641(11)
_cell_length_b                   18.7713(17)
_cell_length_c                   12.8967(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.380(3)
_cell_angle_gamma                90.00
_cell_volume                     2198.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1868
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.962

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             972
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8598
_exptl_absorpt_correction_T_max  0.9649
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10808
_diffrn_reflns_av_R_equivalents  0.1069
_diffrn_reflns_av_sigmaI/netI    0.1122
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3991
_reflns_number_gt                2260
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0979P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3991
_refine_ls_number_parameters     328
_refine_ls_number_restraints     296
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.2120
_refine_ls_wR_factor_gt          0.1853
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.128
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.18495(9) 0.2500 0.74372(7) 0.0568(4) Uani 1 2 d S . .
P1 P 0.1357(2) 0.14889(12) 0.63511(17) 0.0607(6) Uani 1 1 d . . .
S1 S 0.3350(7) 0.7211(4) 0.0891(6) 0.144(3) Uani 0.50 1 d PDU . .
F1 F 0.4646(18) 0.7500 -0.0576(14) 0.221(7) Uani 0.649(13) 2 d SPDU A 1
F2 F 0.2387(14) 0.7007(7) -0.0927(11) 0.238(6) Uani 0.649(13) 1 d PDU A 1
F1' F 0.1863(19) 0.7500 -0.0847(16) 0.221(7) Uani 0.351(13) 2 d SPD A 2
F2' F 0.418(3) 0.6906(13) -0.0256(19) 0.238(6) Uani 0.351(13) 1 d PD A 2
O1 O 0.1346(7) 0.2500 0.4699(6) 0.064(2) Uani 1 2 d S . .
O2 O 0.4579(13) 0.7500 0.1624(11) 0.214(5) Uani 1 2 d SDU . .
O3 O 0.1974(12) 0.7500 0.1079(12) 0.215(5) Uani 1 2 d SDU . .
O4 O 0.3550(19) 0.6472(6) 0.0650(16) 0.206(7) Uani 0.50 1 d PDU . .
C1 C 0.1980(8) 0.1334(5) 0.5122(7) 0.061(2) Uani 1 1 d . . .
C2 C 0.1954(8) 0.1873(5) 0.4428(6) 0.062(2) Uani 1 1 d . . .
C3 C 0.2460(9) 0.1846(5) 0.3483(7) 0.072(2) Uani 1 1 d . . .
C4 C 0.2993(9) 0.1192(6) 0.3249(8) 0.086(3) Uani 1 1 d . . .
H4 H 0.3366 0.1139 0.2635 0.103 Uiso 1 1 calc R . .
C5 C 0.2981(11) 0.0624(6) 0.3901(9) 0.096(3) Uani 1 1 d . . .
H5 H 0.3303 0.0184 0.3703 0.116 Uiso 1 1 calc R . .
C6 C 0.2509(9) 0.0679(5) 0.4843(7) 0.078(3) Uani 1 1 d . . .
H6 H 0.2542 0.0287 0.5288 0.093 Uiso 1 1 calc R . .
C7 C 0.2343(15) 0.2500 0.2789(11) 0.092(4) Uani 1 2 d S . .
C8 C 0.0814(18) 0.2500 0.2049(12) 0.133(6) Uani 1 2 d S . .
H8A H 0.0102 0.2704 0.2412 0.199 Uiso 0.50 1 calc PR . .
H8B H 0.0534 0.2020 0.1847 0.199 Uiso 0.50 1 calc PR . .
H8C H 0.0853 0.2776 0.1429 0.199 Uiso 0.50 1 calc PR . .
C9 C 0.3499(19) 0.2500 0.2118(12) 0.119(6) Uani 1 2 d S . .
H9A H 0.3406 0.2924 0.1694 0.179 Uiso 0.50 1 calc PR . .
H9B H 0.3370 0.2090 0.1665 0.179 Uiso 0.50 1 calc PR . .
H9C H 0.4458 0.2486 0.2566 0.179 Uiso 1 2 calc SR . .
C10 C -0.0622(9) 0.1424(5) 0.5967(7) 0.072(2) Uani 1 1 d . . .
C11 C -0.1434(10) 0.1569(7) 0.6724(9) 0.119(5) Uani 1 1 d . . .
H11 H -0.0959 0.1668 0.7414 0.143 Uiso 1 1 calc R . .
C12 C -0.2971(11) 0.1570(8) 0.6464(11) 0.146(6) Uani 1 1 d . . .
H12 H -0.3516 0.1674 0.6978 0.175 Uiso 1 1 calc R . .
C13 C -0.3642(10) 0.1425(6) 0.5498(11) 0.115(4) Uani 1 1 d . . .
H13 H -0.4665 0.1414 0.5328 0.138 Uiso 1 1 calc R . .
C14 C -0.2853(10) 0.1293(6) 0.4750(9) 0.103(3) Uani 1 1 d . . .
H14 H -0.3343 0.1200 0.4062 0.123 Uiso 1 1 calc R . .
C15 C -0.1343(9) 0.1290(5) 0.4974(8) 0.083(3) Uani 1 1 d . . .
H15 H -0.0820 0.1197 0.4443 0.100 Uiso 1 1 calc R . .
C16 C 0.1980(11) 0.0679(5) 0.7038(7) 0.077(2) Uani 1 1 d . . .
C17 C 0.1058(15) 0.0111(7) 0.7158(9) 0.107(4) Uani 1 1 d . . .
H17 H 0.0052 0.0140 0.6886 0.129 Uiso 1 1 calc R . .
C18 C 0.164(3) -0.0487(10) 0.7676(15) 0.159(8) Uani 1 1 d . . .
H18 H 0.1025 -0.0860 0.7790 0.191 Uiso 1 1 calc R . .
C19 C 0.311(3) -0.0534(11) 0.8023(17) 0.190(12) Uani 1 1 d . . .
H19 H 0.3492 -0.0955 0.8348 0.227 Uiso 1 1 calc R . .
C20 C 0.406(2) -0.0013(10) 0.7928(12) 0.165(7) Uani 1 1 d . . .
H20 H 0.5062 -0.0071 0.8175 0.198 Uiso 1 1 calc R . .
C21 C 0.3485(12) 0.0623(7) 0.7444(9) 0.108(4) Uani 1 1 d . . .
H21 H 0.4107 0.1005 0.7394 0.129 Uiso 1 1 calc R . .
C22 C 0.1580(18) 0.2500 0.9129(11) 0.098(4) Uani 1 2 d SU . .
H22 H 0.0609 0.2500 0.9322 0.118 Uiso 1 2 calc SR . .
C23 C 0.2281(12) 0.1873(6) 0.8934(8) 0.108(3) Uani 1 1 d U . .
H23A H 0.1719 0.1437 0.8936 0.130 Uiso 0.50 1 calc PR B -2
H23B H 0.3304 0.1825 0.9283 0.130 Uiso 0.50 1 calc PR B -2
H23 H 0.3327 0.1926 0.9240 0.130 Uiso 0.50 1 d PR B -2
C24 C 0.178(2) 0.1264(12) 0.9496(18) 0.113(4) Uani 0.50 1 d PDU C -1
C25 C 0.029(2) 0.1149(12) 0.9487(18) 0.121(5) Uani 0.50 1 d PDU C -1
H25 H -0.0387 0.1495 0.9193 0.145 Uiso 0.50 1 calc PR C -1
C26 C -0.023(3) 0.0539(12) 0.990(2) 0.127(5) Uani 0.50 1 d PDU C -1
H26 H -0.1215 0.0458 0.9900 0.153 Uiso 0.50 1 calc PR C -1
C27 C 0.088(2) 0.0063(16) 1.030(2) 0.132(5) Uani 0.50 1 d PDU C -1
H27 H 0.0594 -0.0360 1.0580 0.158 Uiso 0.50 1 calc PR C -1
C28 C 0.237(3) 0.0153(12) 1.0343(19) 0.131(5) Uani 0.50 1 d PDU C -1
H28 H 0.3046 -0.0183 1.0677 0.157 Uiso 0.50 1 calc PR C -1
C29 C 0.285(2) 0.0752(11) 0.9877(17) 0.115(4) Uani 0.50 1 d PDU C -1
H29 H 0.3824 0.0810 0.9821 0.138 Uiso 0.50 1 calc PR C -1
C30 C 0.3295(15) 0.7500 -0.0411(9) 0.199(6) Uani 1 2 d SDU . .


_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
Pd1 C23 2.228(10) 4_565 ?
Pd1 C23 2.228(10) . ?
Pd1 C22 2.244(14) . ?
Pd1 P1 2.349(2) . ?
Pd1 P1 2.349(2) 4_565 ?
P1 C16 1.797(10) . ?
P1 C10 1.807(8) . ?
P1 C1 1.814(8) . ?
S1 S1 1.085(15) 4_575 ?
S1 O2 1.435(9) . ?
S1 O4 1.442(9) . ?
S1 O3 1.449(8) . ?
S1 C30 1.756(9) . ?
F1 C30 1.310(10) . ?
F2 C30 1.337(9) . ?
F1' C30 1.336(11) . ?
F2' C30 1.372(10) . ?
O1 C2 1.379(9) 4_565 ?
O1 C2 1.379(9) . ?
O2 S1 1.435(9) 4_575 ?
O3 S1 1.449(8) 4_575 ?
C1 C2 1.349(11) . ?
C1 C6 1.395(12) . ?
C2 C3 1.391(11) . ?
C3 C4 1.379(13) . ?
C3 C7 1.510(12) . ?
C4 C5 1.360(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(12) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C9 1.504(18) . ?
C7 C3 1.510(12) 4_565 ?
C7 C8 1.54(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.345(11) . ?
C10 C11 1.372(12) . ?
C11 C12 1.397(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.306(15) . ?
C12 H12 0.9300 . ?
C13 C14 1.344(14) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(12) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.393(13) . ?
C16 C17 1.395(13) . ?
C17 C18 1.36(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.36(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.33(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.403(17) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.390(13) 4_565 ?
C22 C23 1.390(12) . ?
C22 H22 0.9800 . ?
C23 C24 1.48(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23 0.9765 . ?
C24 C25 1.396(10) . ?
C24 C29 1.396(10) . ?
C25 C26 1.384(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.384(10) . ?
C26 H26 0.9300 . ?
C27 C28 1.383(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.386(10) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 F2 1.337(9) 4_575 ?
C30 F2' 1.372(10) 4_575 ?
C30 S1 1.756(9) 4_575 ?

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
C23 Pd1 C23 63.7(7) 4_565 . ?
C23 Pd1 C22 36.2(3) 4_565 . ?
C23 Pd1 C22 36.2(3) . . ?
C23 Pd1 P1 157.4(3) 4_565 . ?
C23 Pd1 P1 94.0(3) . . ?
C22 Pd1 P1 122.26(14) . . ?
C23 Pd1 P1 94.0(3) 4_565 4_565 ?
C23 Pd1 P1 157.4(3) . 4_565 ?
C22 Pd1 P1 122.26(14) . 4_565 ?
P1 Pd1 P1 107.77(12) . 4_565 ?
C16 P1 C10 106.7(4) . . ?
C16 P1 C1 99.7(4) . . ?
C10 P1 C1 103.3(4) . . ?
C16 P1 Pd1 112.6(3) . . ?
C10 P1 Pd1 106.6(3) . . ?
C1 P1 Pd1 126.4(3) . . ?
S1 S1 O2 67.8(3) 4_575 . ?
S1 S1 O4 164.2(8) 4_575 . ?
O2 S1 O4 112.8(8) . . ?
S1 S1 O3 68.0(3) 4_575 . ?
O2 S1 O3 111.0(8) . . ?
O4 S1 O3 123.4(9) . . ?
S1 S1 C30 72.0(3) 4_575 . ?
O2 S1 C30 112.5(7) . . ?
O4 S1 C30 94.1(9) . . ?
O3 S1 C30 100.6(7) . . ?
C2 O1 C2 117.1(8) 4_565 . ?
S1 O2 S1 44.4(7) . 4_575 ?
S1 O3 S1 44.0(7) 4_575 . ?
C2 C1 C6 116.8(7) . . ?
C2 C1 P1 119.5(6) . . ?
C6 C1 P1 123.7(7) . . ?
C1 C2 O1 115.3(7) . . ?
C1 C2 C3 126.1(8) . . ?
O1 C2 C3 118.6(8) . . ?
C4 C3 C2 114.9(9) . . ?
C4 C3 C7 125.6(8) . . ?
C2 C3 C7 119.5(9) . . ?
C5 C4 C3 121.1(9) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 122.0(10) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 119.0(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C9 C7 C3 111.4(7) . 4_565 ?
C9 C7 C3 111.4(7) . . ?
C3 C7 C3 108.8(11) 4_565 . ?
C9 C7 C8 108.3(13) . . ?
C3 C7 C8 108.4(8) 4_565 . ?
C3 C7 C8 108.4(8) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.4(8) . . ?
C15 C10 P1 124.0(6) . . ?
C11 C10 P1 117.4(7) . . ?
C10 C11 C12 120.4(10) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.9(10) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.0(9) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 121.7(10) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C10 C15 C14 119.6(9) . . ?
C10 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C21 C16 C17 119.4(10) . . ?
C21 C16 P1 116.7(8) . . ?
C17 C16 P1 123.9(9) . . ?
C18 C17 C16 119.7(14) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 119(2) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C20 C19 C18 124(2) . . ?
C20 C19 H19 118.0 . . ?
C18 C19 H19 118.0 . . ?
C19 C20 C21 118.1(19) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
C16 C21 C20 119.5(13) . . ?
C16 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C23 C22 C23 115.6(15) 4_565 . ?
C23 C22 Pd1 71.3(7) 4_565 . ?
C23 C22 Pd1 71.3(7) . . ?
C23 C22 H22 122.1 4_565 . ?
C23 C22 H22 122.1 . . ?
Pd1 C22 H22 122.1 . . ?
C22 C23 C24 111.3(12) . . ?
C22 C23 Pd1 72.5(7) . . ?
C24 C23 Pd1 144.5(12) . . ?
C22 C23 H23A 116.3 . . ?
C24 C23 H23A 28.9 . . ?
Pd1 C23 H23A 116.3 . . ?
C22 C23 H23B 116.3 . . ?
C24 C23 H23B 94.2 . . ?
Pd1 C23 H23B 116.3 . . ?
H23A C23 H23B 113.3 . . ?
C22 C23 H23 107.6 . . ?
C24 C23 H23 105.3 . . ?
Pd1 C23 H23 106.9 . . ?
H23A C23 H23 125.1 . . ?
H23B C23 H23 11.8 . . ?
C25 C24 C29 122(2) . . ?
C25 C24 C23 121.5(17) . . ?
C29 C24 C23 115.9(17) . . ?
C26 C25 C24 123(2) . . ?
C26 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
C25 C26 C27 113(3) . . ?
C25 C26 H26 123.4 . . ?
C27 C26 H26 123.4 . . ?
C28 C27 C26 126(3) . . ?
C28 C27 H27 116.8 . . ?
C26 C27 H27 116.8 . . ?
C27 C28 C29 119(3) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 H28 120.6 . . ?
C28 C29 C24 117(2) . . ?
C28 C29 H29 121.7 . . ?
C24 C29 H29 121.7 . . ?
F1 C30 F1' 146.4(17) . . ?
F1 C30 F2 116.5(11) . . ?
F1' C30 F2 46.8(8) . . ?
F1 C30 F2 116.5(11) . 4_575 ?
F1' C30 F2 46.8(8) . 4_575 ?
F2 C30 F2 87.7(15) . 4_575 ?
F1 C30 F2' 57.6(17) . 4_575 ?
F1' C30 F2' 125.0(14) . 4_575 ?
F2 C30 F2' 158.8(15) . 4_575 ?
F2 C30 F2' 78.9(13) 4_575 4_575 ?
F1 C30 F2' 57.6(17) . . ?
F1' C30 F2' 125.0(14) . . ?
F2 C30 F2' 78.9(13) . . ?
F2 C30 F2' 158.8(15) 4_575 . ?
F2' C30 F2' 109(3) 4_575 . ?
F1 C30 S1 107.9(10) . 4_575 ?
F1' C30 S1 104.0(11) . 4_575 ?
F2 C30 S1 126.0(10) . 4_575 ?
F2 C30 S1 99.2(9) 4_575 4_575 ?
F2' C30 S1 72.9(13) 4_575 4_575 ?
F2' C30 S1 102.0(11) . 4_575 ?
F1 C30 S1 107.9(10) . . ?
F1' C30 S1 104.0(11) . . ?
F2 C30 S1 99.2(9) . . ?
F2 C30 S1 126.0(10) 4_575 . ?
F2' C30 S1 102.0(11) 4_575 . ?
F2' C30 S1 72.9(13) . . ?
S1 C30 S1 36.0(5) 4_575 . ?

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
C23 Pd1 P1 C16 -25.4(8) 4_565 . . . ?
C23 Pd1 P1 C16 -15.8(4) . . . . ?
C22 Pd1 P1 C16 -40.0(6) . . . . ?
P1 Pd1 P1 C16 170.1(3) 4_565 . . . ?
C23 Pd1 P1 C10 91.3(8) 4_565 . . . ?
C23 Pd1 P1 C10 100.9(4) . . . . ?
C22 Pd1 P1 C10 76.6(6) . . . . ?
P1 Pd1 P1 C10 -73.3(3) 4_565 . . . ?
C23 Pd1 P1 C1 -147.5(8) 4_565 . . . ?
C23 Pd1 P1 C1 -138.0(4) . . . . ?
C22 Pd1 P1 C1 -162.2(6) . . . . ?
P1 Pd1 P1 C1 47.9(4) 4_565 . . . ?
O4 S1 O2 S1 162.9(9) . . . 4_575 ?
O3 S1 O2 S1 -53.9(7) . . . 4_575 ?
C30 S1 O2 S1 58.0(6) . . . 4_575 ?
O2 S1 O3 S1 53.7(7) . . . 4_575 ?
O4 S1 O3 S1 -167.7(11) . . . 4_575 ?
C30 S1 O3 S1 -65.5(5) . . . 4_575 ?
C16 P1 C1 C2 -168.8(7) . . . . ?
C10 P1 C1 C2 81.3(7) . . . . ?
Pd1 P1 C1 C2 -41.3(8) . . . . ?
C16 P1 C1 C6 10.6(8) . . . . ?
C10 P1 C1 C6 -99.3(7) . . . . ?
Pd1 P1 C1 C6 138.1(6) . . . . ?
C6 C1 C2 O1 176.4(7) . . . . ?
P1 C1 C2 O1 -4.2(10) . . . . ?
C6 C1 C2 C3 -2.7(12) . . . . ?
P1 C1 C2 C3 176.7(6) . . . . ?
C2 O1 C2 C1 145.1(6) 4_565 . . . ?
C2 O1 C2 C3 -35.7(12) 4_565 . . . ?
C1 C2 C3 C4 1.8(12) . . . . ?
O1 C2 C3 C4 -177.3(7) . . . . ?
C1 C2 C3 C7 179.7(9) . . . . ?
O1 C2 C3 C7 0.6(12) . . . . ?
C2 C3 C4 C5 1.2(13) . . . . ?
C7 C3 C4 C5 -176.5(10) . . . . ?
C3 C4 C5 C6 -3.2(15) . . . . ?
C4 C5 C6 C1 2.2(15) . . . . ?
C2 C1 C6 C5 0.7(12) . . . . ?
P1 C1 C6 C5 -178.7(7) . . . . ?
C4 C3 C7 C9 -28.7(15) . . . . ?
C2 C3 C7 C9 153.7(10) . . . . ?
C4 C3 C7 C3 -151.9(7) . . . 4_565 ?
C2 C3 C7 C3 30.5(14) . . . 4_565 ?
C4 C3 C7 C8 90.4(12) . . . . ?
C2 C3 C7 C8 -87.2(11) . . . . ?
C16 P1 C10 C15 -104.7(9) . . . . ?
C1 P1 C10 C15 -0.2(10) . . . . ?
Pd1 P1 C10 C15 134.8(8) . . . . ?
C16 P1 C10 C11 80.0(9) . . . . ?
C1 P1 C10 C11 -175.4(9) . . . . ?
Pd1 P1 C10 C11 -40.5(9) . . . . ?
C15 C10 C11 C12 0.6(18) . . . . ?
P1 C10 C11 C12 176.2(10) . . . . ?
C10 C11 C12 C13 1(2) . . . . ?
C11 C12 C13 C14 -2(2) . . . . ?
C12 C13 C14 C15 1(2) . . . . ?
C11 C10 C15 C14 -1.0(16) . . . . ?
P1 C10 C15 C14 -176.2(8) . . . . ?
C13 C14 C15 C10 0.0(18) . . . . ?
C10 P1 C16 C21 -177.8(8) . . . . ?
C1 P1 C16 C21 75.1(8) . . . . ?
Pd1 P1 C16 C21 -61.2(8) . . . . ?
C10 P1 C16 C17 3.9(9) . . . . ?
C1 P1 C16 C17 -103.3(8) . . . . ?
Pd1 P1 C16 C17 120.5(8) . . . . ?
C21 C16 C17 C18 0.5(16) . . . . ?
P1 C16 C17 C18 178.8(10) . . . . ?
C16 C17 C18 C19 -3(2) . . . . ?
C17 C18 C19 C20 3(3) . . . . ?
C18 C19 C20 C21 0(3) . . . . ?
C17 C16 C21 C20 2.6(16) . . . . ?
P1 C16 C21 C20 -175.9(9) . . . . ?
C19 C20 C21 C16 -3(2) . . . . ?
C23 Pd1 C22 C23 126.6(15) . . . 4_565 ?
P1 Pd1 C22 C23 170.5(6) . . . 4_565 ?
P1 Pd1 C22 C23 -43.9(10) 4_565 . . 4_565 ?
C23 Pd1 C22 C23 -126.6(15) 4_565 . . . ?
P1 Pd1 C22 C23 43.9(10) . . . . ?
P1 Pd1 C22 C23 -170.5(6) 4_565 . . . ?
C23 C22 C23 C24 160.1(13) 4_565 . . . ?
Pd1 C22 C23 C24 -142.5(13) . . . . ?
C23 C22 C23 Pd1 -57.4(12) 4_565 . . . ?
C23 Pd1 C23 C22 31.9(9) 4_565 . . . ?
P1 Pd1 C23 C22 -144.0(8) . . . . ?
P1 Pd1 C23 C22 21.3(13) 4_565 . . . ?
C23 Pd1 C23 C24 134.3(18) 4_565 . . . ?
C22 Pd1 C23 C24 102(2) . . . . ?
P1 Pd1 C23 C24 -41.6(19) . . . . ?
P1 Pd1 C23 C24 123.7(18) 4_565 . . . ?
C22 C23 C24 C25 46(3) . . . . ?
Pd1 C23 C24 C25 -44(3) . . . . ?
C22 C23 C24 C29 -144.6(19) . . . . ?
Pd1 C23 C24 C29 125.9(19) . . . . ?
C29 C24 C25 C26 3(4) . . . . ?
C23 C24 C25 C26 172(2) . . . . ?
C24 C25 C26 C27 0(4) . . . . ?
C25 C26 C27 C28 1(4) . . . . ?
C26 C27 C28 C29 -4(4) . . . . ?
C27 C28 C29 C24 7(4) . . . . ?
C25 C24 C29 C28 -6(4) . . . . ?
C23 C24 C29 C28 -175.8(19) . . . . ?
S1 S1 C30 F1 96.0(4) 4_575 . . . ?
O2 S1 C30 F1 40.4(7) . . . . ?
O4 S1 C30 F1 -76.3(8) . . . . ?
O3 S1 C30 F1 158.6(5) . . . . ?
S1 S1 C30 F1' -94.7(4) 4_575 . . . ?
O2 S1 C30 F1' -150.3(6) . . . . ?
O4 S1 C30 F1' 93.0(8) . . . . ?
O3 S1 C30 F1' -32.1(6) . . . . ?
S1 S1 C30 F2 -142.2(8) 4_575 . . . ?
O2 S1 C30 F2 162.2(9) . . . . ?
O4 S1 C30 F2 45.5(10) . . . . ?
O3 S1 C30 F2 -79.7(9) . . . . ?
S1 S1 C30 F2 -48.4(9) 4_575 . . 4_575 ?
O2 S1 C30 F2 -104.0(11) . . . 4_575 ?
O4 S1 C30 F2 139.3(13) . . . 4_575 ?
O3 S1 C30 F2 14.1(12) . . . 4_575 ?
S1 S1 C30 F2' 36.5(17) 4_575 . . 4_575 ?
O2 S1 C30 F2' -19.1(19) . . . 4_575 ?
O4 S1 C30 F2' -135.8(19) . . . 4_575 ?
O3 S1 C30 F2' 99.0(18) . . . 4_575 ?
S1 S1 C30 F2' 142.5(16) 4_575 . . . ?
O2 S1 C30 F2' 86.9(16) . . . . ?
O4 S1 C30 F2' -29.8(16) . . . . ?
O3 S1 C30 F2' -155.0(16) . . . . ?
O2 S1 C30 S1 -55.6(6) . . . 4_575 ?
O4 S1 C30 S1 -172.3(7) . . . 4_575 ?
O3 S1 C30 S1 62.5(5) . . . 4_575 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.108
####################################################################### 
# 
# 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_220627c
_database_code_depnum_ccdc_archive 'CCDC 2249901'
loop_
_audit_author_name
_audit_author_address
'guoying zhang'
;Institute of Coal Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-03-20 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H43 Cl O P2 Pd'
_chemical_formula_weight         839.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   19.3124(17)
_cell_length_b                   18.4281(16)
_cell_length_c                   12.7741(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.027(3)
_cell_angle_gamma                90.00
_cell_volume                     4429.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2653
_cell_measurement_theta_min      2.165
_cell_measurement_theta_max      23.311

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8216
_exptl_absorpt_correction_T_max  0.8725
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10773
_diffrn_reflns_av_R_equivalents  0.1110
_diffrn_reflns_av_sigmaI/netI    0.1586
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3994
_reflns_number_gt                2114
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0998P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3994
_refine_ls_number_parameters     278
_refine_ls_number_restraints     438
_refine_ls_R_factor_all          0.1566
_refine_ls_R_factor_gt           0.0929
_refine_ls_wR_factor_ref         0.2385
_refine_ls_wR_factor_gt          0.2139
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.096
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.37833(4) 0.0000 0.34609(7) 0.0432(4) Uani 1 2 d S . .
P1 P 0.32713(11) 0.10174(14) 0.41178(17) 0.0486(7) Uani 1 1 d . . .
Cl1 Cl 0.5000 0.0392(3) 0.5000 0.151(2) Uani 1 2 d S . .
O1 O 0.3177(4) 0.0000 0.5719(6) 0.047(2) Uani 1 2 d S . .
C1 C 0.3488(4) 0.1197(6) 0.5559(7) 0.065(2) Uani 1 1 d U . .
C2 C 0.3442(4) 0.0634(7) 0.6234(7) 0.069(2) Uani 1 1 d U . .
C3 C 0.3636(5) 0.0643(7) 0.7336(8) 0.080(3) Uani 1 1 d U . .
C4 C 0.3846(5) 0.1330(9) 0.7738(9) 0.092(3) Uani 1 1 d U . .
H4 H 0.3982 0.1385 0.8480 0.110 Uiso 1 1 calc R . .
C5 C 0.3868(6) 0.1948(8) 0.7092(10) 0.096(3) Uani 1 1 d U . .
H5 H 0.3999 0.2399 0.7400 0.115 Uiso 1 1 calc R . .
C6 C 0.3691(5) 0.1866(7) 0.6013(8) 0.079(3) Uani 1 1 d U . .
H6 H 0.3705 0.2264 0.5572 0.095 Uiso 1 1 calc R . .
C7 C 0.3532(7) 0.0000 0.7967(12) 0.085(4) Uani 1 2 d SU . .
C8 C 0.2787(7) 0.0000 0.8149(12) 0.095(5) Uani 1 2 d SU . .
H8A H 0.2701 -0.0450 0.8477 0.143 Uiso 0.50 1 calc PR . .
H8B H 0.2453 0.0054 0.7472 0.143 Uiso 0.50 1 calc PR . .
H8C H 0.2734 0.0396 0.8613 0.143 Uiso 0.50 1 calc PR . .
C9 C 0.4061(10) 0.0000 0.9073(14) 0.128(6) Uani 1 2 d SU . .
H9A H 0.4139 0.0489 0.9329 0.192 Uiso 0.50 1 calc PR . .
H9B H 0.4504 -0.0209 0.9002 0.192 Uiso 0.50 1 calc PR . .
H9C H 0.3868 -0.0281 0.9573 0.192 Uiso 0.50 1 calc PR . .
C10 C 0.2316(5) 0.1016(6) 0.3747(8) 0.068(2) Uani 1 1 d U . .
C11 C 0.2002(5) 0.0903(7) 0.2698(10) 0.091(3) Uani 1 1 d U . .
H11 H 0.2282 0.0805 0.2209 0.109 Uiso 1 1 calc R . .
C12 C 0.1258(6) 0.0932(7) 0.2342(12) 0.107(3) Uani 1 1 d U . .
H12 H 0.1050 0.0905 0.1612 0.128 Uiso 1 1 calc R . .
C13 C 0.0859(6) 0.0998(7) 0.3036(11) 0.095(3) Uani 1 1 d U . .
H13 H 0.0367 0.0983 0.2807 0.114 Uiso 1 1 calc R . .
C14 C 0.1172(5) 0.1092(6) 0.4121(10) 0.083(3) Uani 1 1 d U . .
H14 H 0.0889 0.1139 0.4618 0.099 Uiso 1 1 calc R . .
C15 C 0.1888(5) 0.1115(6) 0.4452(8) 0.068(2) Uani 1 1 d U . .
H15 H 0.2093 0.1199 0.5173 0.082 Uiso 1 1 calc R . .
C16 C 0.3494(4) 0.1891(5) 0.3652(6) 0.047(2) Uani 1 1 d . . .
C17 C 0.3008(5) 0.2395(7) 0.3180(8) 0.068(3) Uani 1 1 d . . .
H17 H 0.2527 0.2284 0.3041 0.081 Uiso 1 1 calc R . .
C18 C 0.3218(7) 0.3056(7) 0.2911(8) 0.078(3) Uani 1 1 d . . .
H18 H 0.2876 0.3395 0.2603 0.093 Uiso 1 1 calc R . .
C19 C 0.3898(8) 0.3233(6) 0.3073(9) 0.077(3) Uani 1 1 d . . .
H19 H 0.4030 0.3690 0.2877 0.093 Uiso 1 1 calc R . .
C20 C 0.4411(6) 0.2734(6) 0.3537(8) 0.068(3) Uani 1 1 d . . .
H20 H 0.4891 0.2849 0.3654 0.081 Uiso 1 1 calc R . .
C21 C 0.4203(4) 0.2084(5) 0.3814(7) 0.051(2) Uani 1 1 d . . .
H21 H 0.4547 0.1748 0.4127 0.062 Uiso 1 1 calc R . .
C22 C 0.4083(8) 0.0000 0.1937(12) 0.065(3) Uani 1 2 d SU . .
H22 H 0.3696 0.0000 0.1291 0.078 Uiso 1 2 calc SR . .
C23 C 0.4283(6) 0.0607(6) 0.2344(10) 0.088(3) Uani 1 1 d U . .
H23A H 0.4026 0.1028 0.2001 0.105 Uiso 1 1 calc R A -2
H23B H 0.4792 0.0683 0.2567 0.105 Uiso 1 1 calc R A -2
H23 H 0.4799 0.0663 0.2581 0.105 Uiso 0.50 1 calc PR A -1
C24 C 0.3880(11) 0.1190(11) 0.1309(15) 0.066(4) Uani 0.50 1 d PU B -1
C25 C 0.3211(12) 0.1131(12) 0.0672(17) 0.073(4) Uani 0.50 1 d PU B -1
H25 H 0.2945 0.0721 0.0744 0.088 Uiso 0.50 1 calc PR B -1
C26 C 0.2932(13) 0.1614(13) -0.0022(17) 0.083(4) Uani 0.50 1 d PU B -1
H26 H 0.2466 0.1568 -0.0418 0.100 Uiso 0.50 1 calc PR B -1
C27 C 0.3331(13) 0.2187(13) -0.0159(18) 0.084(4) Uani 0.50 1 d PU B -1
H27 H 0.3145 0.2520 -0.0695 0.100 Uiso 0.50 1 calc PR B -1
C28 C 0.4033(12) 0.2310(12) 0.0486(16) 0.076(4) Uani 0.50 1 d PU B -1
H28 H 0.4295 0.2719 0.0394 0.091 Uiso 0.50 1 calc PR B -1
C29 C 0.4284(12) 0.1817(11) 0.1208(17) 0.075(4) Uani 0.50 1 d PU B -1
H29 H 0.4731 0.1879 0.1658 0.090 Uiso 0.50 1 calc PR B -1


_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
Pd1 C22 2.152(13) . ?
Pd1 C23 2.199(11) . ?
Pd1 C23 2.199(11) 6 ?
Pd1 P1 2.360(2) 6 ?
Pd1 P1 2.360(2) . ?
Pd1 Cl1 2.7977(18) . ?
Pd1 Cl1 2.7977(18) 5_656 ?
P1 C10 1.799(9) . ?
P1 C16 1.802(10) . ?
P1 C1 1.824(9) . ?
Cl1 Cl1 1.446(12) 5_656 ?
Cl1 Pd1 2.7977(18) 5_656 ?
O1 C2 1.382(10) . ?
O1 C2 1.382(10) 6 ?
C1 C2 1.364(15) . ?
C1 C6 1.380(14) . ?
C2 C3 1.373(13) . ?
C3 C4 1.392(17) . ?
C3 C7 1.471(14) . ?
C4 C5 1.413(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.352(13) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C3 1.471(14) 6 ?
C7 C8 1.508(18) . ?
C7 C9 1.55(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.357(13) . ?
C10 C15 1.364(11) . ?
C11 C12 1.408(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.304(16) . ?
C12 H12 0.9300 . ?
C13 C14 1.392(15) . ?
C13 H13 0.9300 . ?
C14 C15 1.353(12) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.360(13) . ?
C16 C21 1.384(11) . ?
C17 C18 1.351(15) . ?
C17 H17 0.9300 . ?
C18 C19 1.324(14) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(14) . ?
C19 H19 0.9300 . ?
C20 C21 1.338(12) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.257(13) . ?
C22 C23 1.257(13) 6 ?
C22 H22 0.9800 . ?
C23 C24 1.75(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23 0.9800 . ?
C24 C25 1.37(3) . ?
C24 C29 1.42(3) . ?
C25 C26 1.29(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.34(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.44(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.31(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?

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
C22 Pd1 C23 33.6(3) . . ?
C22 Pd1 C23 33.6(3) . 6 ?
C23 Pd1 C23 61.1(6) . 6 ?
C22 Pd1 P1 122.76(15) . 6 ?
C23 Pd1 P1 156.2(3) . 6 ?
C23 Pd1 P1 96.1(3) 6 6 ?
C22 Pd1 P1 122.76(15) . . ?
C23 Pd1 P1 96.1(3) . . ?
C23 Pd1 P1 156.2(3) 6 . ?
P1 Pd1 P1 105.19(12) 6 . ?
C22 Pd1 Cl1 106.3(4) . . ?
C23 Pd1 Cl1 84.4(3) . . ?
C23 Pd1 Cl1 99.5(3) 6 . ?
P1 Pd1 Cl1 107.96(11) 6 . ?
P1 Pd1 Cl1 84.12(11) . . ?
C22 Pd1 Cl1 106.3(4) . 5_656 ?
C23 Pd1 Cl1 99.5(3) . 5_656 ?
C23 Pd1 Cl1 84.4(3) 6 5_656 ?
P1 Pd1 Cl1 84.12(11) 6 5_656 ?
P1 Pd1 Cl1 107.96(11) . 5_656 ?
Cl1 Pd1 Cl1 30.0(2) . 5_656 ?
C10 P1 C16 102.8(5) . . ?
C10 P1 C1 104.7(4) . . ?
C16 P1 C1 98.8(4) . . ?
C10 P1 Pd1 113.1(3) . . ?
C16 P1 Pd1 116.3(3) . . ?
C1 P1 Pd1 119.0(4) . . ?
Cl1 Cl1 Pd1 75.02(12) 5_656 . ?
Cl1 Cl1 Pd1 75.02(12) 5_656 5_656 ?
Pd1 Cl1 Pd1 150.0(2) . 5_656 ?
C2 O1 C2 115.5(11) . 6 ?
C2 C1 C6 117.8(9) . . ?
C2 C1 P1 117.8(8) . . ?
C6 C1 P1 124.4(9) . . ?
C1 C2 C3 126.7(10) . . ?
C1 C2 O1 114.4(8) . . ?
C3 C2 O1 118.9(11) . . ?
C2 C3 C4 112.2(12) . . ?
C2 C3 C7 120.8(11) . . ?
C4 C3 C7 126.5(10) . . ?
C3 C4 C5 124.3(10) . . ?
C3 C4 H4 117.9 . . ?
C5 C4 H4 117.9 . . ?
C6 C5 C4 118.1(11) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 120.8(12) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C3 C7 C3 107.2(13) . 6 ?
C3 C7 C8 109.7(8) . . ?
C3 C7 C8 109.7(8) 6 . ?
C3 C7 C9 110.9(8) . . ?
C3 C7 C9 110.9(8) 6 . ?
C8 C7 C9 108.4(13) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 118.1(9) . . ?
C11 C10 P1 117.6(7) . . ?
C15 C10 P1 124.3(8) . . ?
C10 C11 C12 120.6(11) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.1(13) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.8(11) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.9(10) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 121.2(10) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C17 C16 C21 116.8(9) . . ?
C17 C16 P1 124.4(7) . . ?
C21 C16 P1 118.7(7) . . ?
C18 C17 C16 120.8(9) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 121.7(10) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C20 119.5(11) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 118.7(10) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C20 C21 C16 122.5(9) . . ?
C20 C21 H21 118.8 . . ?
C16 C21 H21 118.8 . . ?
C23 C22 C23 125.7(19) . 6 ?
C23 C22 Pd1 75.3(8) . . ?
C23 C22 Pd1 75.3(8) 6 . ?
C23 C22 H22 116.9 . . ?
C23 C22 H22 116.9 6 . ?
Pd1 C22 H22 116.9 . . ?
C22 C23 C24 101.0(13) . . ?
C22 C23 Pd1 71.2(8) . . ?
C24 C23 Pd1 128.3(9) . . ?
C22 C23 H23A 116.5 . . ?
C24 C23 H23A 21.6 . . ?
Pd1 C23 H23A 116.5 . . ?
C22 C23 H23B 116.5 . . ?
C24 C23 H23B 112.5 . . ?
Pd1 C23 H23B 116.5 . . ?
H23A C23 H23B 113.5 . . ?
C22 C23 H23 114.7 . . ?
C24 C23 H23 114.7 . . ?
Pd1 C23 H23 114.7 . . ?
H23A C23 H23 115.8 . . ?
H23B C23 H23 2.4 . . ?
C25 C24 C29 119(2) . . ?
C25 C24 C23 127.0(17) . . ?
C29 C24 C23 114.2(17) . . ?
C26 C25 C24 123(2) . . ?
C26 C25 H25 118.4 . . ?
C24 C25 H25 118.4 . . ?
C25 C26 C27 118(2) . . ?
C25 C26 H26 121.0 . . ?
C27 C26 H26 121.0 . . ?
C26 C27 C28 123(2) . . ?
C26 C27 H27 118.5 . . ?
C28 C27 H27 118.5 . . ?
C29 C28 C27 117(2) . . ?
C29 C28 H28 121.7 . . ?
C27 C28 H28 121.7 . . ?
C28 C29 C24 120(2) . . ?
C28 C29 H29 119.8 . . ?
C24 C29 H29 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 Pd1 P1 C10 91.4(6) . . . . ?
C23 Pd1 P1 C10 113.3(5) . . . . ?
C23 Pd1 P1 C10 96.7(9) 6 . . . ?
P1 Pd1 P1 C10 -55.9(4) 6 . . . ?
Cl1 Pd1 P1 C10 -162.9(4) . . . . ?
Cl1 Pd1 P1 C10 -144.6(4) 5_656 . . . ?
C22 Pd1 P1 C16 -27.2(6) . . . . ?
C23 Pd1 P1 C16 -5.3(5) . . . . ?
C23 Pd1 P1 C16 -21.9(9) 6 . . . ?
P1 Pd1 P1 C16 -174.5(3) 6 . . . ?
Cl1 Pd1 P1 C16 78.5(3) . . . . ?
Cl1 Pd1 P1 C16 96.8(3) 5_656 . . . ?
C22 Pd1 P1 C1 -145.1(6) . . . . ?
C23 Pd1 P1 C1 -123.2(5) . . . . ?
C23 Pd1 P1 C1 -139.8(9) 6 . . . ?
P1 Pd1 P1 C1 67.6(3) 6 . . . ?
Cl1 Pd1 P1 C1 -39.5(3) . . . . ?
Cl1 Pd1 P1 C1 -21.1(4) 5_656 . . . ?
C22 Pd1 Cl1 Cl1 -94.50(12) . . . 5_656 ?
C23 Pd1 Cl1 Cl1 -120.2(3) . . . 5_656 ?
C23 Pd1 Cl1 Cl1 -60.7(3) 6 . . 5_656 ?
P1 Pd1 Cl1 Cl1 38.95(6) 6 . . 5_656 ?
P1 Pd1 Cl1 Cl1 143.05(6) . . . 5_656 ?
C22 Pd1 Cl1 Pd1 -94.50(12) . . . 5_656 ?
C23 Pd1 Cl1 Pd1 -120.2(3) . . . 5_656 ?
C23 Pd1 Cl1 Pd1 -60.7(3) 6 . . 5_656 ?
P1 Pd1 Cl1 Pd1 38.95(6) 6 . . 5_656 ?
P1 Pd1 Cl1 Pd1 143.05(6) . . . 5_656 ?
Cl1 Pd1 Cl1 Pd1 0.0 5_656 . . 5_656 ?
C10 P1 C1 C2 79.0(8) . . . . ?
C16 P1 C1 C2 -175.2(7) . . . . ?
Pd1 P1 C1 C2 -48.5(8) . . . . ?
C10 P1 C1 C6 -100.5(9) . . . . ?
C16 P1 C1 C6 5.3(9) . . . . ?
Pd1 P1 C1 C6 132.0(8) . . . . ?
C6 C1 C2 C3 -6.2(15) . . . . ?
P1 C1 C2 C3 174.3(8) . . . . ?
C6 C1 C2 O1 174.6(8) . . . . ?
P1 C1 C2 O1 -4.9(11) . . . . ?
C2 O1 C2 C1 147.9(7) 6 . . . ?
C2 O1 C2 C3 -31.4(13) 6 . . . ?
C1 C2 C3 C4 4.9(14) . . . . ?
O1 C2 C3 C4 -175.9(8) . . . . ?
C1 C2 C3 C7 177.8(10) . . . . ?
O1 C2 C3 C7 -3.0(14) . . . . ?
C2 C3 C4 C5 -0.7(15) . . . . ?
C7 C3 C4 C5 -173.1(11) . . . . ?
C3 C4 C5 C6 -1.8(17) . . . . ?
C4 C5 C6 C1 0.7(15) . . . . ?
C2 C1 C6 C5 2.9(14) . . . . ?
P1 C1 C6 C5 -177.6(8) . . . . ?
C2 C3 C7 C3 33.6(16) . . . 6 ?
C4 C3 C7 C3 -154.6(8) . . . 6 ?
C2 C3 C7 C8 -85.4(13) . . . . ?
C4 C3 C7 C8 86.3(14) . . . . ?
C2 C3 C7 C9 154.9(11) . . . . ?
C4 C3 C7 C9 -33.4(17) . . . . ?
C16 P1 C10 C11 76.3(10) . . . . ?
C1 P1 C10 C11 179.1(9) . . . . ?
Pd1 P1 C10 C11 -49.9(10) . . . . ?
C16 P1 C10 C15 -104.2(10) . . . . ?
C1 P1 C10 C15 -1.4(11) . . . . ?
Pd1 P1 C10 C15 129.6(9) . . . . ?
C15 C10 C11 C12 3.8(18) . . . . ?
P1 C10 C11 C12 -176.6(10) . . . . ?
C10 C11 C12 C13 -7(2) . . . . ?
C11 C12 C13 C14 5(2) . . . . ?
C12 C13 C14 C15 0.0(19) . . . . ?
C13 C14 C15 C10 -2.9(17) . . . . ?
C11 C10 C15 C14 0.8(17) . . . . ?
P1 C10 C15 C14 -178.6(9) . . . . ?
C10 P1 C16 C17 2.1(8) . . . . ?
C1 P1 C16 C17 -105.3(8) . . . . ?
Pd1 P1 C16 C17 126.2(7) . . . . ?
C10 P1 C16 C21 179.6(6) . . . . ?
C1 P1 C16 C21 72.2(7) . . . . ?
Pd1 P1 C16 C21 -56.3(7) . . . . ?
C21 C16 C17 C18 -1.5(13) . . . . ?
P1 C16 C17 C18 176.0(7) . . . . ?
C16 C17 C18 C19 1.4(16) . . . . ?
C17 C18 C19 C20 -0.4(17) . . . . ?
C18 C19 C20 C21 -0.3(15) . . . . ?
C19 C20 C21 C16 0.1(14) . . . . ?
C17 C16 C21 C20 0.8(13) . . . . ?
P1 C16 C21 C20 -176.9(7) . . . . ?
C23 Pd1 C22 C23 -133.9(18) 6 . . . ?
P1 Pd1 C22 C23 -176.1(7) 6 . . . ?
P1 Pd1 C22 C23 42.2(11) . . . . ?
Cl1 Pd1 C22 C23 -51.3(9) . . . . ?
Cl1 Pd1 C22 C23 -82.6(9) 5_656 . . . ?
C23 Pd1 C22 C23 133.9(18) . . . 6 ?
P1 Pd1 C22 C23 -42.2(11) 6 . . 6 ?
P1 Pd1 C22 C23 176.1(7) . . . 6 ?
Cl1 Pd1 C22 C23 82.6(9) . . . 6 ?
Cl1 Pd1 C22 C23 51.3(9) 5_656 . . 6 ?
C23 C22 C23 C24 174.0(13) 6 . . . ?
Pd1 C22 C23 C24 -126.9(9) . . . . ?
C23 C22 C23 Pd1 -59.2(15) 6 . . . ?
C23 Pd1 C23 C22 27.1(10) 6 . . . ?
P1 Pd1 C23 C22 8.1(15) 6 . . . ?
P1 Pd1 C23 C22 -145.4(9) . . . . ?
Cl1 Pd1 C23 C22 131.2(9) . . . . ?
Cl1 Pd1 C23 C22 105.2(9) 5_656 . . . ?
C22 Pd1 C23 C24 89.3(15) . . . . ?
C23 Pd1 C23 C24 116.4(11) 6 . . . ?
P1 Pd1 C23 C24 97.5(13) 6 . . . ?
P1 Pd1 C23 C24 -56.0(12) . . . . ?
Cl1 Pd1 C23 C24 -139.5(12) . . . . ?
Cl1 Pd1 C23 C24 -165.4(11) 5_656 . . . ?
C22 C23 C24 C25 41(2) . . . . ?
Pd1 C23 C24 C25 -34(2) . . . . ?
C22 C23 C24 C29 -145.1(15) . . . . ?
Pd1 C23 C24 C29 140.3(13) . . . . ?
C29 C24 C25 C26 1(3) . . . . ?
C23 C24 C25 C26 174.5(18) . . . . ?
C24 C25 C26 C27 3(3) . . . . ?
C25 C26 C27 C28 -5(3) . . . . ?
C26 C27 C28 C29 2(3) . . . . ?
C27 C28 C29 C24 2(3) . . . . ?
C25 C24 C29 C28 -3(3) . . . . ?
C23 C24 C29 C28 -177.8(17) . . . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.000 -0.004 348.7 11.7
2 0.500 0.500 -0.006 348.8 11.7
_platon_squeeze_details          
;
;

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.756
_refine_diff_density_min         -1.381
_refine_diff_density_rms         0.146
####################################################################### 
# 
# 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_230101a
_database_code_depnum_ccdc_archive 'CCDC 2249902'
loop_
_audit_author_name
_audit_author_address
'guoying zhang'
;Institute of Coal Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-03-20 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O'
_chemical_formula_weight         340.41

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4394(7)
_cell_length_b                   10.1901(9)
_cell_length_c                   13.5234(12)
_cell_angle_alpha                98.505(3)
_cell_angle_beta                 92.733(2)
_cell_angle_gamma                110.436(5)
_cell_volume                     944.63(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1583
_cell_measurement_theta_min      2.424
_cell_measurement_theta_max      25.867

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4785
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3278
_reflns_number_gt                1925
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1238P)²+0.0747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.026(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3278
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0731
_refine_ls_wR_factor_ref         0.2311
_refine_ls_wR_factor_gt          0.2015
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6828(3) 0.2793(2) 0.19623(17) 0.0598(7) Uani 1 1 d . . .
N2 N 0.5083(3) 0.1821(2) 0.21594(17) 0.0576(7) Uani 1 1 d . . .
O1 O 0.9969(3) 0.3931(3) 0.25186(17) 0.0909(8) Uani 1 1 d . . .
C1 C 0.8402(4) 0.3109(3) 0.2664(2) 0.0657(8) Uani 1 1 d . . .
C2 C 0.8080(4) 0.2417(4) 0.3592(2) 0.0701(9) Uani 1 1 d . . .
H2A H 0.7115 0.2671 0.3948 0.084 Uiso 1 1 calc R . .
H2B H 0.7599 0.1391 0.3390 0.084 Uiso 1 1 calc R . .
C3 C 0.9921(5) 0.2881(5) 0.4284(3) 0.0915(12) Uani 1 1 d . . .
H3 H 1.0486 0.3857 0.4511 0.110 Uiso 1 1 calc R . .
C4 C 1.0783(5) 0.2179(5) 0.4590(3) 0.0921(12) Uani 1 1 d . . .
H4 H 1.0178 0.1202 0.4382 0.111 Uiso 1 1 calc R . .
C5 C 1.2639(5) 0.2610(4) 0.5242(2) 0.0735(10) Uani 1 1 d . . .
C6 C 1.3495(6) 0.1631(5) 0.5264(3) 0.0898(11) Uani 1 1 d . . .
H6 H 1.2872 0.0714 0.4907 0.108 Uiso 1 1 calc R . .
C7 C 1.5270(6) 0.1970(5) 0.5806(3) 0.0957(12) Uani 1 1 d . . .
H7 H 1.5828 0.1282 0.5792 0.115 Uiso 1 1 calc R . .
C8 C 1.6216(5) 0.3288(5) 0.6356(3) 0.0863(11) Uani 1 1 d . . .
H8 H 1.7413 0.3502 0.6712 0.104 Uiso 1 1 calc R . .
C9 C 1.5386(6) 0.4294(4) 0.6379(3) 0.0885(11) Uani 1 1 d . . .
H9 H 1.6009 0.5196 0.6760 0.106 Uiso 1 1 calc R . .
C10 C 1.3585(6) 0.3960(4) 0.5827(3) 0.0866(11) Uani 1 1 d . . .
H10 H 1.3017 0.4643 0.5850 0.104 Uiso 1 1 calc R . .
C11 C 0.7021(4) 0.3430(3) 0.1060(2) 0.0567(7) Uani 1 1 d . . .
C12 C 0.7014(5) 0.2630(4) 0.0141(2) 0.0727(9) Uani 1 1 d . . .
H12 H 0.6857 0.1676 0.0094 0.087 Uiso 1 1 calc R . .
C13 C 0.7242(5) 0.3258(5) -0.0715(2) 0.0824(11) Uani 1 1 d . . .
H13 H 0.7212 0.2716 -0.1337 0.099 Uiso 1 1 calc R . .
C14 C 0.7510(5) 0.4674(4) -0.0644(3) 0.0792(10) Uani 1 1 d . . .
H14 H 0.7687 0.5096 -0.1214 0.095 Uiso 1 1 calc R . .
C15 C 0.7517(5) 0.5464(4) 0.0274(3) 0.0800(10) Uani 1 1 d . . .
H15 H 0.7690 0.6421 0.0322 0.096 Uiso 1 1 calc R . .
C16 C 0.7266(5) 0.4840(3) 0.1130(2) 0.0686(9) Uani 1 1 d . . .
H16 H 0.7265 0.5378 0.1749 0.082 Uiso 1 1 calc R . .
C17 C 0.3539(4) 0.1633(3) 0.1609(2) 0.0583(7) Uani 1 1 d . . .
H17 H 0.3584 0.2149 0.1092 0.070 Uiso 1 1 calc R . .
C18 C 0.1682(4) 0.0595(3) 0.1795(2) 0.0575(7) Uani 1 1 d . . .
C19 C 0.1611(5) -0.0378(3) 0.2429(2) 0.0680(9) Uani 1 1 d . . .
H19 H 0.2749 -0.0386 0.2738 0.082 Uiso 1 1 calc R . .
C20 C -0.0150(6) -0.1335(4) 0.2600(3) 0.0822(10) Uani 1 1 d . . .
H20 H -0.0188 -0.1975 0.3030 0.099 Uiso 1 1 calc R . .
C21 C -0.1838(5) -0.1339(4) 0.2136(3) 0.0841(11) Uani 1 1 d . . .
H21 H -0.3015 -0.1985 0.2251 0.101 Uiso 1 1 calc R . .
C22 C -0.1790(5) -0.0392(4) 0.1504(3) 0.0832(11) Uani 1 1 d . . .
H22 H -0.2936 -0.0393 0.1198 0.100 Uiso 1 1 calc R . .
C23 C -0.0023(4) 0.0575(3) 0.1317(3) 0.0731(9) Uani 1 1 d . . .
H23 H 0.0007 0.1199 0.0876 0.088 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.383(4) . ?
N1 N2 1.396(3) . ?
N1 C11 1.456(3) . ?
N2 C17 1.278(3) . ?
O1 C1 1.220(3) . ?
C1 C2 1.518(4) . ?
C2 C3 1.506(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.216(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.491(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(5) . ?
C5 C10 1.400(5) . ?
C6 C7 1.384(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.359(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.407(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.372(4) . ?
C11 C12 1.380(4) . ?
C12 C13 1.394(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.477(4) . ?
C17 H17 0.9300 . ?
C18 C23 1.388(4) . ?
C18 C19 1.392(4) . ?
C19 C20 1.387(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.401(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

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
C1 N1 N2 116.6(2) . . ?
C1 N1 C11 120.9(2) . . ?
N2 N1 C11 122.5(2) . . ?
C17 N2 N1 119.0(2) . . ?
O1 C1 N1 119.3(2) . . ?
O1 C1 C2 122.9(2) . . ?
N1 C1 C2 117.8(2) . . ?
C3 C2 C1 111.2(3) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 130.0(4) . . ?
C4 C3 H3 115.0 . . ?
C2 C3 H3 115.0 . . ?
C3 C4 C5 131.2(4) . . ?
C3 C4 H4 114.4 . . ?
C5 C4 H4 114.4 . . ?
C6 C5 C10 117.3(3) . . ?
C6 C5 C4 117.9(3) . . ?
C10 C5 C4 124.8(4) . . ?
C5 C6 C7 121.5(4) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 121.4(4) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 119.1(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 119.8(4) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C5 C10 C9 120.8(4) . . ?
C5 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C16 C11 C12 120.1(3) . . ?
C16 C11 N1 119.7(3) . . ?
C12 C11 N1 120.1(3) . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.7(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 119.8(3) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
N2 C17 C18 119.9(2) . . ?
N2 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C23 C18 C19 119.4(3) . . ?
C23 C18 C17 119.3(3) . . ?
C19 C18 C17 121.3(3) . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 119.5(3) . . ?
C18 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?

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
C1 N1 N2 C17 170.9(3) . . . . ?
C11 N1 N2 C17 -10.3(4) . . . . ?
N2 N1 C1 O1 178.6(3) . . . . ?
C11 N1 C1 O1 -0.2(5) . . . . ?
N2 N1 C1 C2 -1.9(4) . . . . ?
C11 N1 C1 C2 179.2(3) . . . . ?
O1 C1 C2 C3 0.1(5) . . . . ?
N1 C1 C2 C3 -179.3(3) . . . . ?
C1 C2 C3 C4 -121.3(4) . . . . ?
C2 C3 C4 C5 177.4(4) . . . . ?
C3 C4 C5 C6 -164.1(4) . . . . ?
C3 C4 C5 C10 15.1(6) . . . . ?
C10 C5 C6 C7 -2.8(5) . . . . ?
C4 C5 C6 C7 176.4(3) . . . . ?
C5 C6 C7 C8 1.4(6) . . . . ?
C6 C7 C8 C9 0.5(6) . . . . ?
C7 C8 C9 C10 -0.8(6) . . . . ?
C6 C5 C10 C9 2.5(5) . . . . ?
C4 C5 C10 C9 -176.7(3) . . . . ?
C8 C9 C10 C5 -0.7(5) . . . . ?
C1 N1 C11 C16 -72.6(4) . . . . ?
N2 N1 C11 C16 108.6(3) . . . . ?
C1 N1 C11 C12 105.5(3) . . . . ?
N2 N1 C11 C12 -73.3(4) . . . . ?
C16 C11 C12 C13 -0.5(5) . . . . ?
N1 C11 C12 C13 -178.6(3) . . . . ?
C11 C12 C13 C14 1.3(5) . . . . ?
C12 C13 C14 C15 -1.2(5) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C12 C11 C16 C15 -0.3(5) . . . . ?
N1 C11 C16 C15 177.8(3) . . . . ?
C14 C15 C16 C11 0.4(5) . . . . ?
N1 N2 C17 C18 179.1(2) . . . . ?
N2 C17 C18 C23 168.8(3) . . . . ?
N2 C17 C18 C19 -12.2(4) . . . . ?
C23 C18 C19 C20 -1.6(5) . . . . ?
C17 C18 C19 C20 179.4(3) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C19 C20 C21 C22 -0.2(6) . . . . ?
C20 C21 C22 C23 0.7(6) . . . . ?
C19 C18 C23 C22 2.0(5) . . . . ?
C17 C18 C23 C22 -179.0(3) . . . . ?
C21 C22 C23 C18 -1.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.046
