# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_220521g
_database_code_depnum_ccdc_archive 'CCDC 2211820'
loop_
_audit_author_name
_audit_author_address
'guoying zhang'
;Institute of Coal Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-10-08 deposited with the CCDC.	2024-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H18 Cl2 F12 P2 Pd'
_chemical_formula_weight         917.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.3207(11)
_cell_length_b                   10.3560(12)
_cell_length_c                   10.7157(13)
_cell_angle_alpha                111.948(5)
_cell_angle_beta                 107.022(4)
_cell_angle_gamma                101.956(3)
_cell_volume                     948.85(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3302
_cell_measurement_theta_min      2.424
_cell_measurement_theta_max      28.085

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7302
_exptl_absorpt_correction_T_max  0.8132
_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            4648
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3282
_reflns_number_gt                2894
_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)+(0.0793P)²+0.5004P] 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       0.072(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3282
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.5000 0.5000 0.5000 0.0371(2) Uani 1 2 d S . .
P1 P 0.51555(10) 0.70160(10) 0.70730(10) 0.0377(3) Uani 1 1 d . . .
Cl1 Cl 0.33554(11) 0.34995(11) 0.54160(11) 0.0523(3) Uani 1 1 d . . .
F1 F 0.0266(3) 0.6685(5) 0.3740(4) 0.1016(12) Uani 1 1 d . . .
F2 F 0.0757(4) 0.7372(6) 0.8474(4) 0.1147(14) Uani 1 1 d . . .
F3 F 0.7253(4) 0.9352(4) 1.2788(3) 0.0891(10) Uani 1 1 d . . .
F4 F 0.7179(5) 0.4516(4) 1.0166(4) 0.1136(14) Uani 1 1 d . . .
F5 F 1.0142(4) 1.0949(5) 0.8886(5) 0.1139(14) Uani 1 1 d . . .
F6 F 0.6087(4) 1.2075(4) 0.6880(4) 0.1032(12) Uani 1 1 d . . .
C1 C 0.3333(4) 0.7088(4) 0.6786(4) 0.0422(8) Uani 1 1 d . . .
C2 C 0.2486(4) 0.6884(5) 0.5386(5) 0.0533(10) Uani 1 1 d . . .
H2 H 0.2851 0.6744 0.4667 0.064 Uiso 1 1 calc R . .
C3 C 0.1092(5) 0.6898(6) 0.5109(5) 0.0632(12) Uani 1 1 d . . .
C4 C 0.0477(5) 0.7074(6) 0.6119(6) 0.0670(13) Uani 1 1 d . . .
H4 H -0.0463 0.7077 0.5905 0.080 Uiso 1 1 calc R . .
C5 C 0.1346(5) 0.7246(6) 0.7459(6) 0.0663(12) Uani 1 1 d . . .
C6 C 0.2756(5) 0.7259(5) 0.7832(5) 0.0523(10) Uani 1 1 d . . .
H6 H 0.3300 0.7378 0.8756 0.063 Uiso 1 1 calc R . .
C7 C 0.5926(4) 0.6981(4) 0.8833(4) 0.0428(8) Uani 1 1 d . . .
C8 C 0.6278(5) 0.8211(5) 1.0181(4) 0.0509(9) Uani 1 1 d . . .
H8 H 0.6094 0.9059 1.0201 0.061 Uiso 1 1 calc R . .
C9 C 0.6905(5) 0.8151(5) 1.1482(5) 0.0564(11) Uani 1 1 d . . .
C10 C 0.7212(5) 0.6926(6) 1.1522(5) 0.0601(11) Uani 1 1 d . . .
H10 H 0.7630 0.6903 1.2405 0.072 Uiso 1 1 calc R . .
C11 C 0.6864(6) 0.5734(6) 1.0174(6) 0.0635(12) Uani 1 1 d . . .
C12 C 0.6222(5) 0.5716(5) 0.8822(5) 0.0531(10) Uani 1 1 d . . .
H12 H 0.5999 0.4889 0.7940 0.064 Uiso 1 1 calc R . .
C13 C 0.6292(4) 0.8866(4) 0.7465(4) 0.0431(8) Uani 1 1 d . . .
C14 C 0.7800(5) 0.9237(5) 0.8076(5) 0.0566(10) Uani 1 1 d . . .
H14 H 0.8200 0.8602 0.8339 0.068 Uiso 1 1 calc R . .
C15 C 0.8686(5) 1.0578(6) 0.8279(6) 0.0719(14) Uani 1 1 d . . .
C16 C 0.8155(6) 1.1564(6) 0.7901(6) 0.0749(15) Uani 1 1 d . . .
H16 H 0.8767 1.2454 0.8050 0.090 Uiso 1 1 calc R . .
C17 C 0.6654(6) 1.1146(5) 0.7287(6) 0.0690(13) Uani 1 1 d . . .
C18 C 0.5710(5) 0.9829(5) 0.7069(5) 0.0546(10) Uani 1 1 d . . .
H18 H 0.4712 0.9596 0.6668 0.066 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
Pd1 Cl1 2.3157(9) . ?
Pd1 Cl1 2.3157(9) 2_666 ?
Pd1 P1 2.3462(10) 2_666 ?
Pd1 P1 2.3462(10) . ?
P1 C7 1.837(4) . ?
P1 C1 1.837(4) . ?
P1 C13 1.844(4) . ?
F1 C3 1.370(5) . ?
F2 C5 1.373(6) . ?
F3 C9 1.361(6) . ?
F4 C11 1.364(6) . ?
F5 C15 1.353(6) . ?
F6 C17 1.362(6) . ?
C1 C6 1.388(6) . ?
C1 C2 1.406(5) . ?
C2 C3 1.385(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(7) . ?
C4 C5 1.374(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.402(6) . ?
C7 C12 1.403(6) . ?
C8 C9 1.386(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(7) . ?
C10 C11 1.385(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.397(6) . ?
C12 H12 0.9300 . ?
C13 C18 1.396(6) . ?
C13 C14 1.402(6) . ?
C14 C15 1.394(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(8) . ?
C16 C17 1.390(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.394(6) . ?
C18 H18 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
Cl1 Pd1 Cl1 180.00(5) . 2_666 ?
Cl1 Pd1 P1 93.00(3) . 2_666 ?
Cl1 Pd1 P1 87.00(3) 2_666 2_666 ?
Cl1 Pd1 P1 87.00(3) . . ?
Cl1 Pd1 P1 93.00(3) 2_666 . ?
P1 Pd1 P1 180.0 2_666 . ?
C7 P1 C1 108.15(17) . . ?
C7 P1 C13 102.64(17) . . ?
C1 P1 C13 105.72(17) . . ?
C7 P1 Pd1 115.44(13) . . ?
C1 P1 Pd1 108.92(13) . . ?
C13 P1 Pd1 115.30(13) . . ?
C6 C1 C2 120.1(4) . . ?
C6 C1 P1 123.8(3) . . ?
C2 C1 P1 116.0(3) . . ?
C3 C2 C1 118.0(4) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
F1 C3 C4 118.3(4) . . ?
F1 C3 C2 117.8(4) . . ?
C4 C3 C2 123.9(4) . . ?
C5 C4 C3 115.5(4) . . ?
C5 C4 H4 122.2 . . ?
C3 C4 H4 122.2 . . ?
F2 C5 C4 117.3(4) . . ?
F2 C5 C6 118.3(4) . . ?
C4 C5 C6 124.3(4) . . ?
C5 C6 C1 118.1(4) . . ?
C5 C6 H6 121.0 . . ?
C1 C6 H6 121.0 . . ?
C8 C7 C12 119.6(3) . . ?
C8 C7 P1 121.5(3) . . ?
C12 C7 P1 118.9(3) . . ?
C9 C8 C7 119.3(4) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
F3 C9 C10 117.9(4) . . ?
F3 C9 C8 119.1(4) . . ?
C10 C9 C8 122.9(4) . . ?
C9 C10 C11 116.4(4) . . ?
C9 C10 H10 121.8 . . ?
C11 C10 H10 121.8 . . ?
F4 C11 C10 118.2(4) . . ?
F4 C11 C12 118.1(4) . . ?
C10 C11 C12 123.7(4) . . ?
C11 C12 C7 118.0(4) . . ?
C11 C12 H12 121.0 . . ?
C7 C12 H12 121.0 . . ?
C18 C13 C14 119.9(4) . . ?
C18 C13 P1 122.7(3) . . ?
C14 C13 P1 117.1(3) . . ?
C15 C14 C13 118.5(4) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
F5 C15 C16 117.9(5) . . ?
F5 C15 C14 118.7(5) . . ?
C16 C15 C14 123.4(5) . . ?
C15 C16 C17 116.2(4) . . ?
C15 C16 H16 121.9 . . ?
C17 C16 H16 121.9 . . ?
F6 C17 C16 118.0(4) . . ?
F6 C17 C18 118.8(5) . . ?
C16 C17 C18 123.2(5) . . ?
C17 C18 C13 118.8(4) . . ?
C17 C18 H18 120.6 . . ?
C13 C18 H18 120.6 . . ?

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
Cl1 Pd1 P1 C7 64.86(14) . . . . ?
Cl1 Pd1 P1 C7 -115.14(14) 2_666 . . . ?
P1 Pd1 P1 C7 112(100) 2_666 . . . ?
Cl1 Pd1 P1 C1 -57.00(13) . . . . ?
Cl1 Pd1 P1 C1 123.00(13) 2_666 . . . ?
P1 Pd1 P1 C1 -10(100) 2_666 . . . ?
Cl1 Pd1 P1 C13 -175.61(14) . . . . ?
Cl1 Pd1 P1 C13 4.39(14) 2_666 . . . ?
P1 Pd1 P1 C13 -129(100) 2_666 . . . ?
C7 P1 C1 C6 6.6(4) . . . . ?
C13 P1 C1 C6 -102.7(4) . . . . ?
Pd1 P1 C1 C6 132.8(3) . . . . ?
C7 P1 C1 C2 -170.3(3) . . . . ?
C13 P1 C1 C2 80.4(3) . . . . ?
Pd1 P1 C1 C2 -44.1(3) . . . . ?
C6 C1 C2 C3 1.6(6) . . . . ?
P1 C1 C2 C3 178.6(3) . . . . ?
C1 C2 C3 F1 -179.5(4) . . . . ?
C1 C2 C3 C4 -1.2(8) . . . . ?
F1 C3 C4 C5 178.5(5) . . . . ?
C2 C3 C4 C5 0.2(8) . . . . ?
C3 C4 C5 F2 -177.7(5) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
F2 C5 C6 C1 178.2(4) . . . . ?
C4 C5 C6 C1 0.1(8) . . . . ?
C2 C1 C6 C5 -1.1(6) . . . . ?
P1 C1 C6 C5 -177.9(4) . . . . ?
C1 P1 C7 C8 -67.2(4) . . . . ?
C13 P1 C7 C8 44.3(4) . . . . ?
Pd1 P1 C7 C8 170.6(3) . . . . ?
C1 P1 C7 C12 115.6(3) . . . . ?
C13 P1 C7 C12 -132.9(3) . . . . ?
Pd1 P1 C7 C12 -6.6(4) . . . . ?
C12 C7 C8 C9 -0.6(6) . . . . ?
P1 C7 C8 C9 -177.7(3) . . . . ?
C7 C8 C9 F3 179.6(4) . . . . ?
C7 C8 C9 C10 0.4(7) . . . . ?
F3 C9 C10 C11 -179.0(4) . . . . ?
C8 C9 C10 C11 0.2(7) . . . . ?
C9 C10 C11 F4 178.6(5) . . . . ?
C9 C10 C11 C12 -0.7(8) . . . . ?
F4 C11 C12 C7 -178.7(4) . . . . ?
C10 C11 C12 C7 0.5(8) . . . . ?
C8 C7 C12 C11 0.1(6) . . . . ?
P1 C7 C12 C11 177.4(4) . . . . ?
C7 P1 C13 C18 -133.8(4) . . . . ?
C1 P1 C13 C18 -20.5(4) . . . . ?
Pd1 P1 C13 C18 99.9(3) . . . . ?
C7 P1 C13 C14 51.6(4) . . . . ?
C1 P1 C13 C14 164.8(3) . . . . ?
Pd1 P1 C13 C14 -74.8(3) . . . . ?
C18 C13 C14 C15 0.3(7) . . . . ?
P1 C13 C14 C15 175.1(4) . . . . ?
C13 C14 C15 F5 179.2(5) . . . . ?
C13 C14 C15 C16 -0.4(8) . . . . ?
F5 C15 C16 C17 -179.7(5) . . . . ?
C14 C15 C16 C17 -0.2(8) . . . . ?
C15 C16 C17 F6 -179.1(5) . . . . ?
C15 C16 C17 C18 0.9(8) . . . . ?
F6 C17 C18 C13 179.0(4) . . . . ?
C16 C17 C18 C13 -1.0(8) . . . . ?
C14 C13 C18 C17 0.3(7) . . . . ?
P1 C13 C18 C17 -174.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.969
_refine_diff_density_min         -1.149
_refine_diff_density_rms         0.088
####################################################################### 
# 
# 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_220627e
_database_code_depnum_ccdc_archive 'CCDC 2211822'
loop_
_audit_author_name
_audit_author_address
'guoying zhang'
;Institute of Coal Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-10-08 deposited with the CCDC.	2024-05-28 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 Cl N2 O'
_chemical_formula_weight         362.84

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'
Cl Cl 0.1484 0.1585 '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/c

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

_cell_length_a                   28.395(3)
_cell_length_b                   8.7023(9)
_cell_length_c                   19.4102(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 127.674(6)
_cell_angle_gamma                90.00
_cell_volume                     3796.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1573
_cell_measurement_theta_min      2.849
_cell_measurement_theta_max      19.729

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9347
_exptl_absorpt_correction_T_max  0.9727
_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            9403
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3355
_reflns_number_gt                1509
_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)+(0.0850P)²+0.1426P] 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         3355
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1463
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1966
_refine_ls_wR_factor_gt          0.1654
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.00178(5) 0.31135(18) 0.37173(7) 0.1317(6) Uani 1 1 d . . .
N1 N 0.12815(15) 0.3481(3) 0.69435(19) 0.0832(9) Uani 1 1 d . . .
N2 N 0.07080(14) 0.2984(3) 0.6350(2) 0.0779(8) Uani 1 1 d . . .
O1 O 0.19765(18) 0.4259(4) 0.8286(2) 0.1481(15) Uani 1 1 d . . .
C1 C 0.1477(2) 0.3800(5) 0.7766(3) 0.1032(14) Uani 1 1 d . . .
C2 C 0.1062(2) 0.3509(5) 0.7988(3) 0.1012(13) Uani 1 1 d . . .
H2 H 0.0653 0.3497 0.7448 0.121 Uiso 1 1 calc R . .
C3 C 0.1199(2) 0.1974(5) 0.8412(3) 0.0799(11) Uani 1 1 d . . .
C4 C 0.1706(2) 0.1739(6) 0.9223(3) 0.0958(12) Uani 1 1 d . . .
H4 H 0.1977 0.2538 0.9514 0.115 Uiso 1 1 calc R . .
C5 C 0.1825(2) 0.0356(7) 0.9617(3) 0.1052(13) Uani 1 1 d . . .
H5 H 0.2177 0.0210 1.0174 0.126 Uiso 1 1 calc R . .
C6 C 0.1433(3) -0.0815(6) 0.9203(4) 0.1138(15) Uani 1 1 d . . .
H6 H 0.1509 -0.1763 0.9474 0.137 Uiso 1 1 calc R . .
C7 C 0.0937(3) -0.0587(7) 0.8403(4) 0.1281(18) Uani 1 1 d . . .
H7 H 0.0667 -0.1388 0.8107 0.154 Uiso 1 1 calc R . .
C8 C 0.0822(2) 0.0786(6) 0.8016(3) 0.1082(14) Uani 1 1 d . . .
H8 H 0.0470 0.0919 0.7457 0.130 Uiso 1 1 calc R . .
C9 C 0.1123(3) 0.4806(5) 0.8559(3) 0.158(2) Uani 1 1 d . . .
H9A H 0.0861 0.4624 0.8707 0.237 Uiso 1 1 calc R . .
H9B H 0.1020 0.5762 0.8251 0.237 Uiso 1 1 calc R . .
H9C H 0.1526 0.4853 0.9082 0.237 Uiso 1 1 calc R . .
C10 C 0.16719(17) 0.3671(4) 0.6722(2) 0.0742(10) Uani 1 1 d . . .
C11 C 0.2040(2) 0.2511(5) 0.6868(3) 0.0975(13) Uani 1 1 d . . .
H11 H 0.2048 0.1606 0.7129 0.117 Uiso 1 1 calc R . .
C12 C 0.2399(2) 0.2686(7) 0.6625(4) 0.1240(17) Uani 1 1 d . . .
H12 H 0.2649 0.1890 0.6715 0.149 Uiso 1 1 calc R . .
C13 C 0.2392(2) 0.4002(9) 0.6259(3) 0.1189(17) Uani 1 1 d . . .
H13 H 0.2642 0.4127 0.6105 0.143 Uiso 1 1 calc R . .
C14 C 0.2028(3) 0.5121(6) 0.6118(3) 0.1159(15) Uani 1 1 d . . .
H14 H 0.2020 0.6027 0.5857 0.139 Uiso 1 1 calc R . .
C15 C 0.16633(19) 0.4969(5) 0.6349(2) 0.0942(12) Uani 1 1 d . . .
H15 H 0.1410 0.5767 0.6247 0.113 Uiso 1 1 calc R . .
C16 C 0.05200(16) 0.2761(4) 0.5581(2) 0.0733(10) Uani 1 1 d . . .
H16 H 0.0766 0.2939 0.5423 0.088 Uiso 1 1 calc R . .
C17 C -0.00809(16) 0.2225(4) 0.4944(2) 0.0699(9) Uani 1 1 d . . .
C18 C -0.03493(17) 0.2286(4) 0.4073(3) 0.0792(10) Uani 1 1 d . . .
C19 C -0.0912(2) 0.1743(5) 0.3469(3) 0.0993(13) Uani 1 1 d . . .
H19 H -0.1084 0.1782 0.2880 0.119 Uiso 1 1 calc R . .
C20 C -0.1215(2) 0.1158(5) 0.3725(4) 0.1117(15) Uani 1 1 d . . .
H20 H -0.1601 0.0802 0.3313 0.134 Uiso 1 1 calc R . .
C21 C -0.0966(2) 0.1079(5) 0.4570(4) 0.1157(16) Uani 1 1 d . . .
H21 H -0.1179 0.0659 0.4745 0.139 Uiso 1 1 calc R . .
C22 C -0.0403(2) 0.1609(5) 0.5180(3) 0.0999(13) Uani 1 1 d . . .
H22 H -0.0237 0.1547 0.5767 0.120 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
Cl1 C18 1.721(4) . ?
N1 C1 1.361(5) . ?
N1 N2 1.368(4) . ?
N1 C10 1.423(4) . ?
N2 C16 1.256(4) . ?
O1 C1 1.200(5) . ?
C1 C2 1.501(6) . ?
C2 C3 1.491(5) . ?
C2 C9 1.517(5) . ?
C2 H2 0.9800 . ?
C3 C8 1.342(5) . ?
C3 C4 1.349(5) . ?
C4 C5 1.354(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.353(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.327(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.341(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.334(5) . ?
C10 C11 1.352(5) . ?
C11 C12 1.369(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.341(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.322(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.442(5) . ?
C16 H16 0.9300 . ?
C17 C22 1.358(5) . ?
C17 C18 1.367(5) . ?
C18 C19 1.365(5) . ?
C19 C20 1.328(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.334(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.363(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
C1 N1 N2 118.3(3) . . ?
C1 N1 C10 119.8(4) . . ?
N2 N1 C10 121.9(3) . . ?
C16 N2 N1 118.2(3) . . ?
O1 C1 N1 118.6(4) . . ?
O1 C1 C2 123.1(4) . . ?
N1 C1 C2 118.2(4) . . ?
C3 C2 C1 108.9(3) . . ?
C3 C2 C9 112.8(3) . . ?
C1 C2 C9 109.0(4) . . ?
C3 C2 H2 108.7 . . ?
C1 C2 H2 108.7 . . ?
C9 C2 H2 108.7 . . ?
C8 C3 C4 117.4(4) . . ?
C8 C3 C2 121.8(4) . . ?
C4 C3 C2 120.8(4) . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 120.2(5) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 118.8(5) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 120.7(5) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 122.0(5) . . ?
C3 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 120.1(4) . . ?
C15 C10 N1 120.2(4) . . ?
C11 C10 N1 119.7(4) . . ?
C10 C11 C12 119.2(4) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.3(5) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.7(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.1(5) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 119.7(4) . . ?
C10 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
N2 C16 C17 119.3(3) . . ?
N2 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C22 C17 C18 116.8(4) . . ?
C22 C17 C16 121.8(4) . . ?
C18 C17 C16 121.3(3) . . ?
C19 C18 C17 121.6(4) . . ?
C19 C18 Cl1 118.6(3) . . ?
C17 C18 Cl1 119.8(3) . . ?
C20 C19 C18 119.8(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.2(5) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 120.5(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 121.0(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
C1 N1 N2 C16 176.6(3) . . . . ?
C10 N1 N2 C16 -3.2(5) . . . . ?
N2 N1 C1 O1 -178.9(4) . . . . ?
C10 N1 C1 O1 1.0(6) . . . . ?
N2 N1 C1 C2 3.2(5) . . . . ?
C10 N1 C1 C2 -176.9(3) . . . . ?
O1 C1 C2 C3 -81.3(5) . . . . ?
N1 C1 C2 C3 96.5(4) . . . . ?
O1 C1 C2 C9 42.1(6) . . . . ?
N1 C1 C2 C9 -140.1(4) . . . . ?
C1 C2 C3 C8 -110.9(4) . . . . ?
C9 C2 C3 C8 128.0(4) . . . . ?
C1 C2 C3 C4 70.5(5) . . . . ?
C9 C2 C3 C4 -50.6(5) . . . . ?
C8 C3 C4 C5 -0.1(6) . . . . ?
C2 C3 C4 C5 178.5(4) . . . . ?
C3 C4 C5 C6 -0.4(6) . . . . ?
C4 C5 C6 C7 1.1(7) . . . . ?
C5 C6 C7 C8 -1.2(8) . . . . ?
C4 C3 C8 C7 0.1(6) . . . . ?
C2 C3 C8 C7 -178.6(4) . . . . ?
C6 C7 C8 C3 0.6(8) . . . . ?
C1 N1 C10 C15 -95.6(4) . . . . ?
N2 N1 C10 C15 84.3(4) . . . . ?
C1 N1 C10 C11 86.4(4) . . . . ?
N2 N1 C10 C11 -93.8(4) . . . . ?
C15 C10 C11 C12 -0.3(6) . . . . ?
N1 C10 C11 C12 177.8(4) . . . . ?
C10 C11 C12 C13 1.0(7) . . . . ?
C11 C12 C13 C14 -1.2(8) . . . . ?
C12 C13 C14 C15 0.8(8) . . . . ?
C11 C10 C15 C14 -0.1(6) . . . . ?
N1 C10 C15 C14 -178.2(4) . . . . ?
C13 C14 C15 C10 -0.1(7) . . . . ?
N1 N2 C16 C17 179.5(3) . . . . ?
N2 C16 C17 C22 -16.0(5) . . . . ?
N2 C16 C17 C18 165.4(3) . . . . ?
C22 C17 C18 C19 -0.5(5) . . . . ?
C16 C17 C18 C19 178.2(3) . . . . ?
C22 C17 C18 Cl1 177.6(3) . . . . ?
C16 C17 C18 Cl1 -3.7(5) . . . . ?
C17 C18 C19 C20 1.0(6) . . . . ?
Cl1 C18 C19 C20 -177.2(3) . . . . ?
C18 C19 C20 C21 -1.0(7) . . . . ?
C19 C20 C21 C22 0.6(7) . . . . ?
C18 C17 C22 C21 0.1(6) . . . . ?
C16 C17 C22 C21 -178.6(4) . . . . ?
C20 C21 C22 C17 -0.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_220903b
_database_code_depnum_ccdc_archive 'CCDC 2211824'
loop_
_audit_author_name
_audit_author_address
'guoying zhang'
;Institute of Coal Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-10-08 deposited with the CCDC.	2024-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H21 N2 O'
_chemical_formula_weight         377.45

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   25.693(3)
_cell_length_b                   10.5137(15)
_cell_length_c                   17.6798(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.976(6)
_cell_angle_gamma                90.00
_cell_volume                     4006.4(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2372
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      21.239

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1592
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_T_max  0.9759
_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            9863
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3541
_reflns_number_gt                1991
_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)+(0.1340P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0065(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3541
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0716
_refine_ls_wR_factor_ref         0.2420
_refine_ls_wR_factor_gt          0.2083
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.95366(11) 0.8343(2) 0.31067(16) 0.0533(7) Uani 1 1 d . . .
N2 N 0.91699(12) 0.7352(2) 0.25776(15) 0.0537(7) Uani 1 1 d . . .
O1 O 1.04949(10) 0.8961(2) 0.41753(14) 0.0674(7) Uani 1 1 d . . .
C1 C 1.01553(15) 0.8102(3) 0.3731(2) 0.0552(8) Uani 1 1 d . . .
C2 C 1.03810(16) 0.6772(3) 0.3831(2) 0.0636(9) Uani 1 1 d . . .
H2 H 1.0608 0.6480 0.3599 0.076 Uiso 1 1 calc R . .
C3 C 1.02022(17) 0.5963(4) 0.4343(2) 0.0699(10) Uani 1 1 d . . .
H3A H 0.9755 0.5862 0.3996 0.084 Uiso 1 1 calc R . .
H3B H 1.0324 0.6381 0.4906 0.084 Uiso 1 1 calc R . .
C4 C 1.05050(17) 0.4668(3) 0.4542(2) 0.0602(9) Uani 1 1 d . . .
C5 C 1.02013(19) 0.3725(4) 0.3951(3) 0.0759(11) Uani 1 1 d . . .
H5 H 0.9820 0.3898 0.3426 0.091 Uiso 1 1 calc R . .
C6 C 1.0435(2) 0.2518(4) 0.4096(3) 0.0801(11) Uani 1 1 d . . .
H6 H 1.0214 0.1898 0.3661 0.096 Uiso 1 1 calc R . .
C7 C 1.0965(2) 0.2213(4) 0.4839(3) 0.0734(11) Uani 1 1 d . . .
H7 H 1.1102 0.1374 0.4935 0.088 Uiso 1 1 calc R . .
C8 C 1.13271(16) 0.3150(4) 0.5491(2) 0.0639(10) Uani 1 1 d . . .
C9 C 1.10921(16) 0.4409(3) 0.5339(2) 0.0585(9) Uani 1 1 d . . .
C10 C 1.1445(2) 0.5328(4) 0.5980(3) 0.0859(12) Uani 1 1 d . . .
H10 H 1.1300 0.6161 0.5888 0.103 Uiso 1 1 calc R . .
C11 C 1.1978(2) 0.5041(6) 0.6715(3) 0.1131(17) Uani 1 1 d . . .
H11 H 1.2204 0.5675 0.7136 0.136 Uiso 1 1 calc R . .
C12 C 1.2216(2) 0.3809(7) 0.6881(3) 0.119(2) Uani 1 1 d . . .
H12 H 1.2597 0.3628 0.7404 0.143 Uiso 1 1 calc R . .
C13 C 1.1884(2) 0.2868(5) 0.6271(3) 0.0971(14) Uani 1 1 d . . .
H13 H 1.2034 0.2039 0.6384 0.117 Uiso 1 1 calc R . .
C14 C 0.92975(13) 0.9594(3) 0.30249(18) 0.0505(8) Uani 1 1 d . . .
C15 C 0.92019(15) 1.0049(3) 0.3666(2) 0.0611(9) Uani 1 1 d . . .
H15 H 0.9300 0.9549 0.4161 0.073 Uiso 1 1 calc R . .
C16 C 0.89631(16) 1.1232(4) 0.3576(2) 0.0676(10) Uani 1 1 d . . .
H16 H 0.8902 1.1545 0.4014 0.081 Uiso 1 1 calc R . .
C17 C 0.88125(15) 1.1963(4) 0.2849(2) 0.0668(10) Uani 1 1 d . . .
H17 H 0.8642 1.2767 0.2784 0.080 Uiso 1 1 calc R . .
C18 C 0.89128(16) 1.1511(3) 0.2215(2) 0.0653(10) Uani 1 1 d . . .
H18 H 0.8815 1.2014 0.1721 0.078 Uiso 1 1 calc R . .
C19 C 0.91555(15) 1.0332(3) 0.2300(2) 0.0593(9) Uani 1 1 d . . .
H19 H 0.9224 1.0028 0.1868 0.071 Uiso 1 1 calc R . .
C20 C 0.85913(16) 0.7534(3) 0.2055(2) 0.0594(9) Uani 1 1 d . . .
H20 H 0.8425 0.8319 0.2055 0.071 Uiso 1 1 calc R . .
C21 C 0.81840(14) 0.6541(3) 0.1456(2) 0.0537(8) Uani 1 1 d . . .
C22 C 0.83999(15) 0.5396(3) 0.1375(2) 0.0625(9) Uani 1 1 d . . .
H22 H 0.8822 0.5215 0.1738 0.075 Uiso 1 1 calc R . .
C23 C 0.80016(18) 0.4511(4) 0.0766(3) 0.0753(11) Uani 1 1 d . . .
H23 H 0.8155 0.3738 0.0713 0.090 Uiso 1 1 calc R . .
C24 C 0.73843(19) 0.4756(5) 0.0240(2) 0.0805(12) Uani 1 1 d . . .
H24 H 0.7117 0.4154 -0.0177 0.097 Uiso 1 1 calc R . .
C25 C 0.71567(18) 0.5876(4) 0.0321(3) 0.0831(12) Uani 1 1 d . . .
H25 H 0.6732 0.6036 -0.0027 0.100 Uiso 1 1 calc R . .
C26 C 0.75579(17) 0.6771(4) 0.0920(2) 0.0725(10) Uani 1 1 d . . .
H26 H 0.7403 0.7548 0.0963 0.087 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 1.374(3) . ?
N1 C1 1.378(4) . ?
N1 C14 1.426(4) . ?
N2 C20 1.267(4) . ?
O1 C1 1.203(4) . ?
C1 C2 1.487(5) . ?
C2 C3 1.486(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.512(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.340(5) . ?
C4 C9 1.422(5) . ?
C5 C6 1.368(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.317(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.413(5) . ?
C7 H7 0.9300 . ?
C8 C13 1.374(5) . ?
C8 C9 1.418(5) . ?
C9 C10 1.386(5) . ?
C10 C11 1.312(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.366(4) . ?
C14 C15 1.369(4) . ?
C15 C16 1.358(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.360(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.359(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.449(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(5) . ?
C21 C26 1.373(5) . ?
C22 C23 1.369(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.357(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.357(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.371(5) . ?
C25 H25 0.9300 . ?
C26 H26 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 C1 118.1(3) . . ?
N2 N1 C14 122.2(2) . . ?
C1 N1 C14 119.7(3) . . ?
C20 N2 N1 118.7(3) . . ?
O1 C1 N1 119.7(3) . . ?
O1 C1 C2 122.1(3) . . ?
N1 C1 C2 118.2(3) . . ?
C3 C2 C1 112.4(3) . . ?
C3 C2 H2 123.8 . . ?
C1 C2 H2 123.8 . . ?
C2 C3 C4 111.5(3) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C9 119.0(3) . . ?
C5 C4 C3 118.5(3) . . ?
C9 C4 C3 122.5(3) . . ?
C4 C5 C6 122.0(4) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 121.6(4) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 120.5(4) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C13 C8 C7 122.1(4) . . ?
C13 C8 C9 119.6(4) . . ?
C7 C8 C9 118.2(3) . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 C4 123.1(3) . . ?
C8 C9 C4 118.6(3) . . ?
C11 C10 C9 121.0(5) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 121.6(5) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C8 119.8(5) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C19 C14 C15 120.0(3) . . ?
C19 C14 N1 120.0(3) . . ?
C15 C14 N1 120.0(3) . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C14 119.6(3) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
N2 C20 C21 121.2(3) . . ?
N2 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C26 118.2(3) . . ?
C22 C21 C20 122.6(3) . . ?
C26 C21 C20 119.1(3) . . ?
C21 C22 C23 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.3(4) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.2(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 119.4(4) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C21 121.2(4) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?

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 C20 174.2(3) . . . . ?
C14 N1 N2 C20 -6.1(4) . . . . ?
N2 N1 C1 O1 176.5(3) . . . . ?
C14 N1 C1 O1 -3.2(5) . . . . ?
N2 N1 C1 C2 -3.4(4) . . . . ?
C14 N1 C1 C2 176.8(3) . . . . ?
O1 C1 C2 C3 103.6(4) . . . . ?
N1 C1 C2 C3 -76.4(4) . . . . ?
C1 C2 C3 C4 -172.6(3) . . . . ?
C2 C3 C4 C5 -91.1(4) . . . . ?
C2 C3 C4 C9 90.3(4) . . . . ?
C9 C4 C5 C6 0.9(6) . . . . ?
C3 C4 C5 C6 -177.9(4) . . . . ?
C4 C5 C6 C7 1.8(6) . . . . ?
C5 C6 C7 C8 -3.5(6) . . . . ?
C6 C7 C8 C13 -179.6(4) . . . . ?
C6 C7 C8 C9 2.5(5) . . . . ?
C13 C8 C9 C10 1.7(5) . . . . ?
C7 C8 C9 C10 179.6(3) . . . . ?
C13 C8 C9 C4 -177.8(3) . . . . ?
C7 C8 C9 C4 0.1(5) . . . . ?
C5 C4 C9 C10 178.8(4) . . . . ?
C3 C4 C9 C10 -2.5(5) . . . . ?
C5 C4 C9 C8 -1.7(5) . . . . ?
C3 C4 C9 C8 177.0(3) . . . . ?
C8 C9 C10 C11 -0.9(6) . . . . ?
C4 C9 C10 C11 178.6(4) . . . . ?
C9 C10 C11 C12 0.5(7) . . . . ?
C10 C11 C12 C13 -0.8(8) . . . . ?
C11 C12 C13 C8 1.5(7) . . . . ?
C7 C8 C13 C12 -179.8(4) . . . . ?
C9 C8 C13 C12 -2.0(6) . . . . ?
N2 N1 C14 C19 -73.5(4) . . . . ?
C1 N1 C14 C19 106.2(3) . . . . ?
N2 N1 C14 C15 105.6(3) . . . . ?
C1 N1 C14 C15 -74.7(4) . . . . ?
C19 C14 C15 C16 0.3(5) . . . . ?
N1 C14 C15 C16 -178.8(3) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C15 C16 C17 C18 -1.2(5) . . . . ?
C16 C17 C18 C19 0.7(5) . . . . ?
C17 C18 C19 C14 0.2(5) . . . . ?
C15 C14 C19 C18 -0.7(5) . . . . ?
N1 C14 C19 C18 178.3(3) . . . . ?
N1 N2 C20 C21 177.7(2) . . . . ?
N2 C20 C21 C22 -4.5(5) . . . . ?
N2 C20 C21 C26 178.2(3) . . . . ?
C26 C21 C22 C23 0.9(5) . . . . ?
C20 C21 C22 C23 -176.5(3) . . . . ?
C21 C22 C23 C24 -0.7(6) . . . . ?
C22 C23 C24 C25 -0.6(6) . . . . ?
C23 C24 C25 C26 1.8(6) . . . . ?
C24 C25 C26 C21 -1.7(6) . . . . ?
C22 C21 C26 C25 0.4(5) . . . . ?
C20 C21 C26 C25 177.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_220903a
_database_code_depnum_ccdc_archive 'CCDC 2211821'
loop_
_audit_author_name
_audit_author_address
'guoying zhang'
;Institute of Coal Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-10-08 deposited with the CCDC.	2024-05-28 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 H18 F2 N2 O'
_chemical_formula_weight         364.38

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'
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                   19.924(2)
_cell_length_b                   9.8441(11)
_cell_length_c                   9.3555(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.522(3)
_cell_angle_gamma                90.00
_cell_volume                     1829.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1651
_cell_measurement_theta_min      2.309
_cell_measurement_theta_max      28.295

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_T_max  0.9933
_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            3184
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1413
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3184
_reflns_number_gt                1510
_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)+(0.0582P)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         3184
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1861
_refine_ls_R_factor_gt           0.0921
_refine_ls_wR_factor_ref         0.2020
_refine_ls_wR_factor_gt          0.1735
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_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 0.57674(12) 0.4916(3) 0.6173(3) 0.0906(9) Uani 1 1 d . . .
F2 F 0.68281(12) 0.8020(3) 0.9249(3) 0.0854(9) Uani 1 1 d . . .
N1 N 0.67920(14) 0.5440(3) 0.8190(4) 0.0552(9) Uani 1 1 d . . .
N2 N 0.74412(14) 0.5421(3) 0.7817(3) 0.0546(9) Uani 1 1 d . . .
O1 O 0.60482(14) 0.4437(3) 0.9473(3) 0.0752(9) Uani 1 1 d . . .
C1 C 0.6609(2) 0.4422(5) 0.9058(4) 0.0611(11) Uani 1 1 d . . .
C2 C 0.71094(19) 0.3323(4) 0.9447(5) 0.0610(11) Uani 1 1 d . . .
H2 H 0.7336 0.3083 0.8589 0.073 Uiso 1 1 calc R . .
C3 C 0.76283(19) 0.3772(4) 1.0580(4) 0.0563(10) Uani 1 1 d . . .
C4 C 0.7468(2) 0.4544(5) 1.1731(5) 0.0711(13) Uani 1 1 d . . .
H4 H 0.7026 0.4836 1.1787 0.085 Uiso 1 1 calc R . .
C5 C 0.7940(3) 0.4881(5) 1.2777(5) 0.0793(14) Uani 1 1 d . . .
H5 H 0.7816 0.5396 1.3547 0.095 Uiso 1 1 calc R . .
C6 C 0.8589(3) 0.4493(5) 1.2742(6) 0.0871(16) Uani 1 1 d . . .
H6 H 0.8910 0.4734 1.3474 0.105 Uiso 1 1 calc R . .
C7 C 0.8760(2) 0.3738(6) 1.1600(7) 0.0942(17) Uani 1 1 d . . .
H7 H 0.9204 0.3463 1.1549 0.113 Uiso 1 1 calc R . .
C8 C 0.8293(2) 0.3390(5) 1.0549(6) 0.0783(13) Uani 1 1 d . . .
H8 H 0.8421 0.2878 0.9781 0.094 Uiso 1 1 calc R . .
C9 C 0.6746(2) 0.2074(5) 0.9943(5) 0.0873(16) Uani 1 1 d . . .
H9A H 0.7065 0.1353 1.0136 0.131 Uiso 1 1 calc R . .
H9B H 0.6412 0.1794 0.9206 0.131 Uiso 1 1 calc R . .
H9C H 0.6532 0.2285 1.0799 0.131 Uiso 1 1 calc R . .
C10 C 0.63179(17) 0.6433(4) 0.7713(4) 0.0500(10) Uani 1 1 d . . .
C11 C 0.58098(19) 0.6173(5) 0.6725(4) 0.0606(11) Uani 1 1 d . . .
C12 C 0.5346(2) 0.7096(5) 0.6224(5) 0.0711(13) Uani 1 1 d . . .
H12 H 0.5006 0.6868 0.5525 0.085 Uiso 1 1 calc R . .
C13 C 0.5396(2) 0.8372(5) 0.6782(5) 0.0743(13) Uani 1 1 d . . .
H13 H 0.5085 0.9032 0.6464 0.089 Uiso 1 1 calc R . .
C14 C 0.5895(2) 0.8693(5) 0.7798(5) 0.0706(12) Uani 1 1 d . . .
H14 H 0.5928 0.9568 0.8174 0.085 Uiso 1 1 calc R . .
C15 C 0.63398(19) 0.7737(5) 0.8254(4) 0.0600(11) Uani 1 1 d . . .
C16 C 0.76455(17) 0.6372(4) 0.7041(4) 0.0514(10) Uani 1 1 d . . .
H16 H 0.7353 0.7068 0.6734 0.062 Uiso 1 1 calc R . .
C17 C 0.83317(17) 0.6375(4) 0.6633(4) 0.0523(10) Uani 1 1 d . . .
C18 C 0.8531(2) 0.7407(5) 0.5785(5) 0.0678(12) Uani 1 1 d . . .
H18 H 0.8224 0.8072 0.5464 0.081 Uiso 1 1 calc R . .
C19 C 0.9180(2) 0.7472(6) 0.5403(5) 0.0828(15) Uani 1 1 d . . .
H19 H 0.9311 0.8172 0.4820 0.099 Uiso 1 1 calc R . .
C20 C 0.9627(2) 0.6514(6) 0.5879(6) 0.0885(16) Uani 1 1 d . . .
H20 H 1.0070 0.6569 0.5638 0.106 Uiso 1 1 calc R . .
C21 C 0.9438(2) 0.5472(6) 0.6703(5) 0.0825(15) Uani 1 1 d . . .
H21 H 0.9748 0.4809 0.7020 0.099 Uiso 1 1 calc R . .
C22 C 0.8783(2) 0.5404(5) 0.7067(5) 0.0727(13) Uani 1 1 d . . .
H22 H 0.8649 0.4682 0.7619 0.087 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 C11 1.341(5) . ?
F2 C15 1.322(4) . ?
N1 C1 1.358(5) . ?
N1 N2 1.366(4) . ?
N1 C10 1.407(5) . ?
N2 C16 1.271(5) . ?
O1 C1 1.211(5) . ?
C1 C2 1.497(6) . ?
C2 C3 1.488(5) . ?
C2 C9 1.518(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.377(6) . ?
C3 C8 1.379(5) . ?
C4 C5 1.344(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.352(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.367(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.344(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.341(5) . ?
C10 C15 1.379(5) . ?
C11 C12 1.354(6) . ?
C12 C13 1.361(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.340(6) . ?
C14 H14 0.9300 . ?
C16 C17 1.448(5) . ?
C16 H16 0.9300 . ?
C17 C22 1.352(5) . ?
C17 C18 1.368(6) . ?
C18 C19 1.369(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.348(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.355(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.376(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
C1 N1 N2 116.6(3) . . ?
C1 N1 C10 119.8(3) . . ?
N2 N1 C10 123.7(3) . . ?
C16 N2 N1 119.2(3) . . ?
O1 C1 N1 118.8(4) . . ?
O1 C1 C2 123.0(4) . . ?
N1 C1 C2 118.2(4) . . ?
C3 C2 C1 111.8(3) . . ?
C3 C2 C9 110.1(4) . . ?
C1 C2 C9 109.6(3) . . ?
C3 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
C9 C2 H2 108.4 . . ?
C4 C3 C8 116.7(4) . . ?
C4 C3 C2 122.0(4) . . ?
C8 C3 C2 121.2(4) . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 122.0(5) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C7 118.0(5) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C8 C7 C6 120.6(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C3 121.8(5) . . ?
C7 C8 H8 119.1 . . ?
C3 C8 H8 119.1 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 115.6(4) . . ?
C11 C10 N1 122.5(4) . . ?
C15 C10 N1 121.9(3) . . ?
C10 C11 F1 117.6(4) . . ?
C10 C11 C12 124.6(4) . . ?
F1 C11 C12 117.7(4) . . ?
C11 C12 C13 117.3(4) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.3(5) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
F2 C15 C14 120.5(4) . . ?
F2 C15 C10 117.1(4) . . ?
C14 C15 C10 122.4(4) . . ?
N2 C16 C17 120.2(4) . . ?
N2 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C22 C17 C18 118.8(4) . . ?
C22 C17 C16 122.6(4) . . ?
C18 C17 C16 118.6(4) . . ?
C19 C18 C17 120.6(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.6(5) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.7(5) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C22 119.3(5) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C17 C22 C21 120.8(5) . . ?
C17 C22 H22 119.6 . . ?
C21 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
C1 N1 N2 C16 -177.9(3) . . . . ?
C10 N1 N2 C16 2.8(5) . . . . ?
N2 N1 C1 O1 176.3(3) . . . . ?
C10 N1 C1 O1 -4.3(6) . . . . ?
N2 N1 C1 C2 -4.2(5) . . . . ?
C10 N1 C1 C2 175.2(3) . . . . ?
O1 C1 C2 C3 -102.8(5) . . . . ?
N1 C1 C2 C3 77.8(5) . . . . ?
O1 C1 C2 C9 19.6(6) . . . . ?
N1 C1 C2 C9 -159.9(4) . . . . ?
C1 C2 C3 C4 40.8(5) . . . . ?
C9 C2 C3 C4 -81.3(5) . . . . ?
C1 C2 C3 C8 -141.6(4) . . . . ?
C9 C2 C3 C8 96.3(5) . . . . ?
C8 C3 C4 C5 -1.0(7) . . . . ?
C2 C3 C4 C5 176.7(4) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
C4 C5 C6 C7 0.1(8) . . . . ?
C5 C6 C7 C8 -0.3(8) . . . . ?
C6 C7 C8 C3 -0.2(8) . . . . ?
C4 C3 C8 C7 0.8(7) . . . . ?
C2 C3 C8 C7 -176.9(4) . . . . ?
C1 N1 C10 C11 -72.5(5) . . . . ?
N2 N1 C10 C11 106.8(4) . . . . ?
C1 N1 C10 C15 106.3(4) . . . . ?
N2 N1 C10 C15 -74.4(5) . . . . ?
C15 C10 C11 F1 -179.8(4) . . . . ?
N1 C10 C11 F1 -0.9(6) . . . . ?
C15 C10 C11 C12 1.8(6) . . . . ?
N1 C10 C11 C12 -179.3(4) . . . . ?
C10 C11 C12 C13 -1.0(7) . . . . ?
F1 C11 C12 C13 -179.5(4) . . . . ?
C11 C12 C13 C14 0.2(7) . . . . ?
C12 C13 C14 C15 -0.2(7) . . . . ?
C13 C14 C15 F2 -179.6(4) . . . . ?
C13 C14 C15 C10 1.1(7) . . . . ?
C11 C10 C15 F2 178.8(3) . . . . ?
N1 C10 C15 F2 0.0(6) . . . . ?
C11 C10 C15 C14 -1.8(6) . . . . ?
N1 C10 C15 C14 179.3(4) . . . . ?
N1 N2 C16 C17 179.9(3) . . . . ?
N2 C16 C17 C22 -1.2(6) . . . . ?
N2 C16 C17 C18 179.3(4) . . . . ?
C22 C17 C18 C19 -1.2(7) . . . . ?
C16 C17 C18 C19 178.3(4) . . . . ?
C17 C18 C19 C20 -0.5(7) . . . . ?
C18 C19 C20 C21 1.5(8) . . . . ?
C19 C20 C21 C22 -0.6(8) . . . . ?
C18 C17 C22 C21 2.1(6) . . . . ?
C16 C17 C22 C21 -177.4(4) . . . . ?
C20 C21 C22 C17 -1.2(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_220627d
_database_code_depnum_ccdc_archive 'CCDC 2211823'
loop_
_audit_author_name
_audit_author_address
'guoying zhang'
;Institute of Coal Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-10-08 deposited with the CCDC.	2024-05-28 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 Cl N2 O'
_chemical_formula_weight         362.84

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'
Cl Cl 0.1484 0.1585 '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)/n

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

_cell_length_a                   9.6555(9)
_cell_length_b                   19.9306(17)
_cell_length_c                   10.6995(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.967(5)
_cell_angle_gamma                90.00
_cell_volume                     1851.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2075
_cell_measurement_theta_min      2.541
_cell_measurement_theta_max      20.435

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9174
_exptl_absorpt_correction_T_max  0.9432
_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            9408
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_av_sigmaI/netI    0.0736
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3259
_reflns_number_gt                1847
_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)+(0.1269P)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       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3259
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0768
_refine_ls_wR_factor_ref         0.2378
_refine_ls_wR_factor_gt          0.2122
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Cl1 Cl 0.87889(16) 0.52611(7) 1.11866(14) 0.1128(6) Uani 1 1 d . . .
N1 N 0.3358(3) 0.63353(13) 0.4499(3) 0.0530(7) Uani 1 1 d . . .
N2 N 0.2783(3) 0.57399(14) 0.4733(3) 0.0553(7) Uani 1 1 d . . .
O1 O 0.4362(3) 0.73215(12) 0.5354(3) 0.0707(8) Uani 1 1 d . . .
C1 C 0.3783(4) 0.68098(17) 0.5504(4) 0.0542(9) Uani 1 1 d . . .
C2 C 0.3515(4) 0.66751(17) 0.6745(3) 0.0567(9) Uani 1 1 d . . .
H2 H 0.2617 0.6379 0.6462 0.068 Uiso 1 1 calc R . .
C3 C 0.4869(4) 0.63187(17) 0.7833(3) 0.0549(9) Uani 1 1 d . . .
C4 C 0.4791(5) 0.56535(19) 0.8111(4) 0.0737(11) Uani 1 1 d . . .
H4 H 0.3889 0.5416 0.7594 0.088 Uiso 1 1 calc R . .
C5 C 0.6000(5) 0.5333(2) 0.9123(4) 0.0791(12) Uani 1 1 d . . .
H5 H 0.5926 0.4879 0.9289 0.095 Uiso 1 1 calc R . .
C6 C 0.7300(5) 0.5669(2) 0.9885(4) 0.0706(11) Uani 1 1 d . . .
C7 C 0.7420(5) 0.6321(2) 0.9631(4) 0.0703(11) Uani 1 1 d . . .
H7 H 0.8328 0.6553 1.0151 0.084 Uiso 1 1 calc R . .
C8 C 0.6210(5) 0.66408(18) 0.8609(4) 0.0650(10) Uani 1 1 d . . .
H8 H 0.6305 0.7092 0.8438 0.078 Uiso 1 1 calc R . .
C9 C 0.3144(5) 0.73233(19) 0.7257(4) 0.0774(12) Uani 1 1 d . . .
H9A H 0.4019 0.7617 0.7565 0.116 Uiso 1 1 calc R . .
H9B H 0.2896 0.7232 0.8018 0.116 Uiso 1 1 calc R . .
H9C H 0.2279 0.7534 0.6516 0.116 Uiso 1 1 calc R . .
C10 C 0.3564(4) 0.64392(16) 0.3277(3) 0.0518(8) Uani 1 1 d . . .
C11 C 0.4960(5) 0.63359(19) 0.3295(4) 0.0685(10) Uani 1 1 d . . .
H11 H 0.5794 0.6212 0.4119 0.082 Uiso 1 1 calc R . .
C12 C 0.5143(6) 0.6412(2) 0.2124(5) 0.0803(13) Uani 1 1 d . . .
H12 H 0.6103 0.6346 0.2136 0.096 Uiso 1 1 calc R . .
C13 C 0.3923(7) 0.6583(2) 0.0942(5) 0.0862(14) Uani 1 1 d . . .
H13 H 0.4037 0.6626 0.0127 0.103 Uiso 1 1 calc R . .
C14 C 0.2534(6) 0.6695(2) 0.0915(4) 0.0869(14) Uani 1 1 d . . .
H14 H 0.1705 0.6821 0.0089 0.104 Uiso 1 1 calc R . .
C15 C 0.2341(5) 0.66242(19) 0.2095(4) 0.0687(11) Uani 1 1 d . . .
H15 H 0.1387 0.6702 0.2086 0.082 Uiso 1 1 calc R . .
C16 C 0.2529(4) 0.52690(17) 0.3883(4) 0.0564(9) Uani 1 1 d . . .
H16 H 0.2738 0.5325 0.3120 0.068 Uiso 1 1 calc R . .
C17 C 0.1910(4) 0.46390(17) 0.4085(4) 0.0573(9) Uani 1 1 d . . .
C18 C 0.1773(5) 0.41218(19) 0.3193(4) 0.0747(11) Uani 1 1 d . . .
H18 H 0.2061 0.4185 0.2478 0.090 Uiso 1 1 calc R . .
C19 C 0.1219(5) 0.3517(2) 0.3348(6) 0.0888(14) Uani 1 1 d . . .
H19 H 0.1126 0.3168 0.2740 0.107 Uiso 1 1 calc R . .
C20 C 0.0800(5) 0.3425(2) 0.4400(6) 0.0888(14) Uani 1 1 d . . .
H20 H 0.0430 0.3010 0.4514 0.107 Uiso 1 1 calc R . .
C21 C 0.0920(4) 0.3930(2) 0.5272(5) 0.0744(11) Uani 1 1 d . . .
H21 H 0.0623 0.3864 0.5981 0.089 Uiso 1 1 calc R . .
C22 C 0.1476(4) 0.45415(18) 0.5123(4) 0.0624(10) Uani 1 1 d . . .
H22 H 0.1556 0.4890 0.5730 0.075 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
Cl1 C6 1.707(4) . ?
N1 C1 1.354(4) . ?
N1 N2 1.379(4) . ?
N1 C10 1.421(4) . ?
N2 C16 1.254(4) . ?
O1 C1 1.207(4) . ?
C1 C2 1.485(5) . ?
C2 C3 1.496(5) . ?
C2 C9 1.507(5) . ?
C2 H2 0.9800 . ?
C3 C8 1.355(5) . ?
C3 C4 1.368(5) . ?
C4 C5 1.356(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.339(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.343(6) . ?
C7 C8 1.359(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.350(5) . ?
C10 C11 1.355(5) . ?
C11 C12 1.349(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.342(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.347(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.447(5) . ?
C16 H16 0.9300 . ?
C17 C22 1.362(5) . ?
C17 C18 1.371(5) . ?
C18 C19 1.357(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.341(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(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
C1 N1 N2 117.6(3) . . ?
C1 N1 C10 120.9(3) . . ?
N2 N1 C10 121.5(3) . . ?
C16 N2 N1 118.7(3) . . ?
O1 C1 N1 118.8(3) . . ?
O1 C1 C2 123.0(3) . . ?
N1 C1 C2 118.2(3) . . ?
C1 C2 C3 110.3(3) . . ?
C1 C2 C9 109.4(3) . . ?
C3 C2 C9 113.0(3) . . ?
C1 C2 H2 108.0 . . ?
C3 C2 H2 108.0 . . ?
C9 C2 H2 108.0 . . ?
C8 C3 C4 117.1(4) . . ?
C8 C3 C2 121.8(3) . . ?
C4 C3 C2 121.1(3) . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C6 C5 C4 120.0(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.1(4) . . ?
C5 C6 Cl1 119.3(3) . . ?
C7 C6 Cl1 120.6(3) . . ?
C6 C7 C8 119.8(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C7 121.6(4) . . ?
C3 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 120.7(3) . . ?
C15 C10 N1 119.0(3) . . ?
C11 C10 N1 120.2(3) . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.1(4) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 121.2(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C15 120.1(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 118.6(4) . . ?
C10 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N2 C16 C17 120.3(3) . . ?
N2 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C22 C17 C18 119.3(4) . . ?
C22 C17 C16 122.7(3) . . ?
C18 C17 C16 118.0(4) . . ?
C19 C18 C17 120.4(4) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.6(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.4(4) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.3(4) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 119.9(4) . . ?
C17 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?

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 C16 -172.9(3) . . . . ?
C10 N1 N2 C16 4.4(4) . . . . ?
N2 N1 C1 O1 176.3(3) . . . . ?
C10 N1 C1 O1 -1.0(5) . . . . ?
N2 N1 C1 C2 -3.7(4) . . . . ?
C10 N1 C1 C2 179.0(3) . . . . ?
O1 C1 C2 C3 -91.3(4) . . . . ?
N1 C1 C2 C3 88.6(4) . . . . ?
O1 C1 C2 C9 33.5(5) . . . . ?
N1 C1 C2 C9 -146.5(3) . . . . ?
C1 C2 C3 C8 74.4(4) . . . . ?
C9 C2 C3 C8 -48.4(5) . . . . ?
C1 C2 C3 C4 -107.3(4) . . . . ?
C9 C2 C3 C4 129.9(4) . . . . ?
C8 C3 C4 C5 0.4(6) . . . . ?
C2 C3 C4 C5 -178.0(4) . . . . ?
C3 C4 C5 C6 0.7(7) . . . . ?
C4 C5 C6 C7 -1.3(7) . . . . ?
C4 C5 C6 Cl1 178.2(3) . . . . ?
C5 C6 C7 C8 0.9(6) . . . . ?
Cl1 C6 C7 C8 -178.6(3) . . . . ?
C4 C3 C8 C7 -0.8(6) . . . . ?
C2 C3 C8 C7 177.6(3) . . . . ?
C6 C7 C8 C3 0.2(6) . . . . ?
C1 N1 C10 C15 -100.8(4) . . . . ?
N2 N1 C10 C15 82.0(4) . . . . ?
C1 N1 C10 C11 80.9(4) . . . . ?
N2 N1 C10 C11 -96.3(4) . . . . ?
C15 C10 C11 C12 -0.5(6) . . . . ?
N1 C10 C11 C12 177.7(3) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
C11 C12 C13 C14 1.5(7) . . . . ?
C12 C13 C14 C15 -1.1(7) . . . . ?
C11 C10 C15 C14 1.0(6) . . . . ?
N1 C10 C15 C14 -177.3(3) . . . . ?
C13 C14 C15 C10 -0.2(6) . . . . ?
N1 N2 C16 C17 -179.4(3) . . . . ?
N2 C16 C17 C22 4.8(5) . . . . ?
N2 C16 C17 C18 -174.7(3) . . . . ?
C22 C17 C18 C19 -0.4(6) . . . . ?
C16 C17 C18 C19 179.1(4) . . . . ?
C17 C18 C19 C20 -0.1(7) . . . . ?
C18 C19 C20 C21 0.6(7) . . . . ?
C19 C20 C21 C22 -0.5(7) . . . . ?
C18 C17 C22 C21 0.5(6) . . . . ?
C16 C17 C22 C21 -179.0(3) . . . . ?
C20 C21 C22 C17 0.0(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.063
