# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_zhk003
_audit_block_doi                 10.5517/ccdc.csd.cc251h3v
_database_code_depnum_ccdc_archive 'CCDC 1997426'
loop_
_audit_author_name
_audit_author_address
JD
;SCU
China
;
_audit_update_record             
;
2020-05-30 deposited with the CCDC.	2022-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H25 N O'
_chemical_formula_sum            'C26 H25 N O'
_chemical_formula_weight         367.47

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   8.8182(5)
_cell_length_b                   9.1071(6)
_cell_length_c                   13.4452(9)
_cell_angle_alpha                77.090(3)
_cell_angle_beta                 77.721(3)
_cell_angle_gamma                66.321(2)
_cell_volume                     954.67(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    4668
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.198
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6491
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23625
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_av_R_equivalents  0.1103
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.472
_diffrn_reflns_theta_max         26.538
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3943
_reflns_number_gt                2761
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+0.4895P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.056(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3943
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.83747(18) 0.20699(17) 0.47377(12) 0.0291(4) Uani 1 1 d . . . . .
N N 0.9518(2) 0.0053(2) 0.37278(14) 0.0262(4) Uani 1 1 d . . . . .
H1 H 1.026(3) -0.070(3) 0.415(2) 0.046(8) Uiso 1 1 d . . . . .
C1 C 0.8426(2) 0.1505(2) 0.39821(16) 0.0243(5) Uani 1 1 d . . . . .
C2 C 0.7212(2) 0.2330(2) 0.31553(16) 0.0233(5) Uani 1 1 d . . . . .
C3 C 0.7368(2) 0.4001(2) 0.26625(16) 0.0239(5) Uani 1 1 d . . . . .
H3 H 0.709337 0.462275 0.324496 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6091(3) 0.5038(2) 0.19146(17) 0.0260(5) Uani 1 1 d . . . . .
H4A H 0.651968 0.468962 0.122881 0.031 Uiso 1 1 calc R U . . .
H4B H 0.502829 0.486258 0.216801 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5764(3) 0.6826(3) 0.18130(18) 0.0297(5) Uani 1 1 d . . . . .
H5 H 0.685023 0.699244 0.163155 0.036 Uiso 1 1 calc R U . . .
C6 C 0.4510(3) 0.8062(3) 0.10813(19) 0.0354(6) Uani 1 1 d . . . . .
H6A H 0.365070 0.768906 0.097987 0.042 Uiso 1 1 calc R U . . .
H6B H 0.504902 0.847184 0.041473 0.042 Uiso 1 1 calc R U . . .
C7 C 0.3904(3) 0.9223(3) 0.1899(2) 0.0443(7) Uani 1 1 d . . . . .
H7A H 0.443039 1.003997 0.174947 0.053 Uiso 1 1 calc R U . . .
H7B H 0.267234 0.974224 0.204587 0.053 Uiso 1 1 calc R U . . .
C8 C 0.4687(3) 0.7751(3) 0.2719(2) 0.0397(6) Uani 1 1 d . . . . .
H8A H 0.388490 0.727762 0.314833 0.048 Uiso 1 1 calc R U . . .
H8B H 0.534480 0.795127 0.315041 0.048 Uiso 1 1 calc R U . . .
C11 C 0.9224(3) -0.0230(2) 0.28193(16) 0.0248(5) Uani 1 1 d . . . . .
C12 C 0.7892(2) 0.1086(2) 0.24320(16) 0.0238(5) Uani 1 1 d . . . . .
C13 C 0.7407(3) 0.1053(3) 0.15280(17) 0.0289(5) Uani 1 1 d . . . . .
H13 H 0.649566 0.193759 0.125543 0.035 Uiso 1 1 calc R U . . .
C14 C 0.8263(3) -0.0285(3) 0.10202(18) 0.0323(5) Uani 1 1 d . . . . .
H14 H 0.794781 -0.030446 0.039156 0.039 Uiso 1 1 calc R U . . .
C15 C 0.9569(3) -0.1586(3) 0.14252(19) 0.0345(5) Uani 1 1 d . . . . .
H15 H 1.013085 -0.249892 0.107521 0.041 Uiso 1 1 calc R U . . .
C16 C 1.0074(3) -0.1584(3) 0.23328(18) 0.0317(5) Uani 1 1 d . . . . .
H16 H 1.097116 -0.247849 0.261144 0.038 Uiso 1 1 calc R U . . .
C21 C 0.5456(2) 0.2507(2) 0.37164(16) 0.0247(5) Uani 1 1 d . . . . .
C22 C 0.4803(3) 0.1334(3) 0.37618(18) 0.0311(5) Uani 1 1 d . . . . .
H22 H 0.543808 0.042593 0.341583 0.037 Uiso 1 1 calc R U . . .
C23 C 0.3243(3) 0.1461(3) 0.43013(19) 0.0356(6) Uani 1 1 d . . . . .
H23 H 0.281731 0.064799 0.431720 0.043 Uiso 1 1 calc R U . . .
C24 C 0.2304(3) 0.2763(3) 0.48167(19) 0.0363(6) Uani 1 1 d . . . . .
H24 H 0.123847 0.284488 0.519278 0.044 Uiso 1 1 calc R U . . .
C25 C 0.2931(3) 0.3949(3) 0.47796(18) 0.0339(5) Uani 1 1 d . . . . .
H25 H 0.228651 0.485817 0.512284 0.041 Uiso 1 1 calc R U . . .
C26 C 0.4496(3) 0.3814(3) 0.42436(17) 0.0295(5) Uani 1 1 d . . . . .
H26 H 0.492323 0.462327 0.423476 0.035 Uiso 1 1 calc R U . . .
C31 C 0.9142(2) 0.3843(2) 0.21726(17) 0.0246(5) Uani 1 1 d . . . . .
C32 C 0.9820(3) 0.3385(3) 0.12066(18) 0.0317(5) Uani 1 1 d . . . . .
H32 H 0.918437 0.310378 0.084499 0.038 Uiso 1 1 calc R U . . .
C33 C 1.1403(3) 0.3331(3) 0.07626(19) 0.0352(6) Uani 1 1 d . . . . .
H33 H 1.184067 0.302042 0.009948 0.042 Uiso 1 1 calc R U . . .
C34 C 1.2352(3) 0.3726(3) 0.12785(19) 0.0344(6) Uani 1 1 d . . . . .
H34 H 1.343325 0.370441 0.096793 0.041 Uiso 1 1 calc R U . . .
C35 C 1.1719(3) 0.4151(3) 0.22450(19) 0.0331(5) Uani 1 1 d . . . . .
H35 H 1.237328 0.439943 0.261128 0.040 Uiso 1 1 calc R U . . .
C36 C 1.0124(3) 0.4216(3) 0.26849(18) 0.0293(5) Uani 1 1 d . . . . .
H36 H 0.969383 0.452134 0.334973 0.035 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O C1 1.223(3) . ?
N C1 1.353(3) . ?
N C11 1.398(3) . ?
C1 C2 1.560(3) . ?
C2 C12 1.512(3) . ?
C2 C21 1.533(3) . ?
C2 C3 1.566(3) . ?
C3 C31 1.525(3) . ?
C3 C4 1.541(3) . ?
C4 C5 1.514(3) . ?
C5 C8 1.556(3) . ?
C5 C6 1.557(3) . ?
C6 C7 1.558(4) . ?
C7 C8 1.552(3) . ?
C11 C16 1.385(3) . ?
C11 C12 1.392(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.391(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.386(3) . ?
C21 C22 1.389(3) . ?
C21 C26 1.395(3) . ?
C22 C23 1.384(3) . ?
C23 C24 1.381(4) . ?
C24 C25 1.386(3) . ?
C25 C26 1.385(3) . ?
C31 C32 1.389(3) . ?
C31 C36 1.390(3) . ?
C32 C33 1.382(3) . ?
C33 C34 1.383(3) . ?
C34 C35 1.376(3) . ?
C35 C36 1.388(3) . ?

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 N C11 111.59(18) . . ?
O C1 N 126.17(19) . . ?
O C1 C2 125.46(18) . . ?
N C1 C2 108.35(18) . . ?
C12 C2 C21 113.13(16) . . ?
C12 C2 C1 101.07(16) . . ?
C21 C2 C1 106.63(16) . . ?
C12 C2 C3 114.15(17) . . ?
C21 C2 C3 112.85(16) . . ?
C1 C2 C3 107.90(16) . . ?
C31 C3 C4 111.48(17) . . ?
C31 C3 C2 113.14(16) . . ?
C4 C3 C2 113.46(16) . . ?
C5 C4 C3 111.47(17) . . ?
C4 C5 C8 118.68(19) . . ?
C4 C5 C6 118.69(19) . . ?
C8 C5 C6 89.31(17) . . ?
C5 C6 C7 87.30(18) . . ?
C8 C7 C6 89.39(18) . . ?
C7 C8 C5 87.57(19) . . ?
C16 C11 C12 122.2(2) . . ?
C16 C11 N 127.88(19) . . ?
C12 C11 N 109.96(18) . . ?
C13 C12 C11 119.12(19) . . ?
C13 C12 C2 131.87(19) . . ?
C11 C12 C2 109.00(17) . . ?
C12 C13 C14 119.5(2) . . ?
C15 C14 C13 120.4(2) . . ?
C14 C15 C16 121.2(2) . . ?
C11 C16 C15 117.7(2) . . ?
C22 C21 C26 117.8(2) . . ?
C22 C21 C2 121.20(19) . . ?
C26 C21 C2 120.92(18) . . ?
C23 C22 C21 121.3(2) . . ?
C24 C23 C22 120.3(2) . . ?
C23 C24 C25 119.3(2) . . ?
C26 C25 C24 120.2(2) . . ?
C25 C26 C21 121.1(2) . . ?
C32 C31 C36 117.7(2) . . ?
C32 C31 C3 122.58(18) . . ?
C36 C31 C3 119.71(19) . . ?
C33 C32 C31 121.1(2) . . ?
C32 C33 C34 120.4(2) . . ?
C35 C34 C33 119.5(2) . . ?
C34 C35 C36 120.0(2) . . ?
C35 C36 C31 121.4(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
C11 N C1 O 179.46(19) . . . . ?
C11 N C1 C2 0.5(2) . . . . ?
O C1 C2 C12 179.67(19) . . . . ?
N C1 C2 C12 -1.4(2) . . . . ?
O C1 C2 C21 -61.9(3) . . . . ?
N C1 C2 C21 117.08(18) . . . . ?
O C1 C2 C3 59.6(3) . . . . ?
N C1 C2 C3 -121.44(18) . . . . ?
C12 C2 C3 C31 -53.3(2) . . . . ?
C21 C2 C3 C31 175.69(17) . . . . ?
C1 C2 C3 C31 58.2(2) . . . . ?
C12 C2 C3 C4 75.0(2) . . . . ?
C21 C2 C3 C4 -56.0(2) . . . . ?
C1 C2 C3 C4 -173.56(17) . . . . ?
C31 C3 C4 C5 -75.1(2) . . . . ?
C2 C3 C4 C5 155.76(18) . . . . ?
C3 C4 C5 C8 -73.9(2) . . . . ?
C3 C4 C5 C6 179.63(18) . . . . ?
C4 C5 C6 C7 141.7(2) . . . . ?
C8 C5 C6 C7 18.98(18) . . . . ?
C5 C6 C7 C8 -19.02(18) . . . . ?
C6 C7 C8 C5 19.03(18) . . . . ?
C4 C5 C8 C7 -141.8(2) . . . . ?
C6 C5 C8 C7 -19.05(18) . . . . ?
C1 N C11 C16 -179.3(2) . . . . ?
C1 N C11 C12 0.7(2) . . . . ?
C16 C11 C12 C13 -0.5(3) . . . . ?
N C11 C12 C13 179.49(18) . . . . ?
C16 C11 C12 C2 178.34(19) . . . . ?
N C11 C12 C2 -1.6(2) . . . . ?
C21 C2 C12 C13 66.8(3) . . . . ?
C1 C2 C12 C13 -179.5(2) . . . . ?
C3 C2 C12 C13 -64.0(3) . . . . ?
C21 C2 C12 C11 -111.85(19) . . . . ?
C1 C2 C12 C11 1.8(2) . . . . ?
C3 C2 C12 C11 117.29(19) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C2 C12 C13 C14 -179.1(2) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C16 -1.0(4) . . . . ?
C12 C11 C16 C15 0.8(3) . . . . ?
N C11 C16 C15 -179.2(2) . . . . ?
C14 C15 C16 C11 0.0(3) . . . . ?
C12 C2 C21 C22 16.7(3) . . . . ?
C1 C2 C21 C22 -93.5(2) . . . . ?
C3 C2 C21 C22 148.3(2) . . . . ?
C12 C2 C21 C26 -166.60(19) . . . . ?
C1 C2 C21 C26 83.2(2) . . . . ?
C3 C2 C21 C26 -35.1(3) . . . . ?
C26 C21 C22 C23 0.7(3) . . . . ?
C2 C21 C22 C23 177.5(2) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C22 C23 C24 C25 0.6(4) . . . . ?
C23 C24 C25 C26 -1.0(3) . . . . ?
C24 C25 C26 C21 1.2(3) . . . . ?
C22 C21 C26 C25 -1.1(3) . . . . ?
C2 C21 C26 C25 -177.86(19) . . . . ?
C4 C3 C31 C32 -50.0(3) . . . . ?
C2 C3 C31 C32 79.3(2) . . . . ?
C4 C3 C31 C36 127.9(2) . . . . ?
C2 C3 C31 C36 -102.8(2) . . . . ?
C36 C31 C32 C33 -1.2(3) . . . . ?
C3 C31 C32 C33 176.8(2) . . . . ?
C31 C32 C33 C34 0.4(3) . . . . ?
C32 C33 C34 C35 1.0(3) . . . . ?
C33 C34 C35 C36 -1.5(3) . . . . ?
C34 C35 C36 C31 0.7(3) . . . . ?
C32 C31 C36 C35 0.7(3) . . . . ?
C3 C31 C36 C35 -177.33(19) . . . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_zhk004
_database_code_depnum_ccdc_archive 'CCDC 1997427'
loop_
_audit_author_name
_audit_author_address
JD
;SCU
China
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2022-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 F N O'
_chemical_formula_sum            'C23 H20 F N O'
_chemical_formula_weight         345.40

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   7.2842(2)
_cell_length_b                   10.4854(3)
_cell_length_c                   13.1094(4)
_cell_angle_alpha                66.4510(10)
_cell_angle_beta                 79.5030(10)
_cell_angle_gamma                72.7980(10)
_cell_volume                     874.47(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9994
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      26.42

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.118
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21700
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.221
_diffrn_reflns_theta_max         26.438
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3545
_reflns_number_gt                3092
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0323P)²+0.3960P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3545
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F 0.68431(12) 0.87699(9) 0.00346(8) 0.0437(2) Uani 1 1 d . . . . .
O O 0.07317(12) 0.53146(10) 0.34477(7) 0.0293(2) Uani 1 1 d . . . . .
N N 0.25682(15) 0.40994(11) 0.49442(9) 0.0247(2) Uani 1 1 d . . . . .
H1 H 0.162(3) 0.4270(18) 0.5445(14) 0.044(5) Uiso 1 1 d . . . . .
C1 C 0.22725(17) 0.45778(13) 0.38506(10) 0.0230(3) Uani 1 1 d . . . . .
C2 C 0.41860(16) 0.40143(13) 0.32221(10) 0.0205(2) Uani 1 1 d . . . . .
C3 C 0.38001(17) 0.29914(13) 0.26819(10) 0.0229(3) Uani 1 1 d . . . . .
C4 C 0.26612(19) 0.19778(15) 0.35699(12) 0.0310(3) Uani 1 1 d . . . . .
H4A H 0.139724 0.253836 0.374993 0.047 Uiso 1 1 calc R U . . .
H4B H 0.337004 0.145495 0.424433 0.047 Uiso 1 1 calc R U . . .
H4C H 0.248883 0.129261 0.328273 0.047 Uiso 1 1 calc R U . . .
C5 C 0.25713(18) 0.38333(15) 0.16716(11) 0.0298(3) Uani 1 1 d . . . . .
H5A H 0.133237 0.437559 0.189892 0.045 Uiso 1 1 calc R U . . .
H5B H 0.234826 0.316176 0.138747 0.045 Uiso 1 1 calc R U . . .
H5C H 0.325029 0.449919 0.108471 0.045 Uiso 1 1 calc R U . . .
C11 C 0.44388(17) 0.32427(13) 0.51769(10) 0.0219(2) Uani 1 1 d . . . . .
C12 C 0.54720(16) 0.31392(12) 0.41941(10) 0.0210(2) Uani 1 1 d . . . . .
C13 C 0.73606(17) 0.23121(13) 0.42531(10) 0.0226(3) Uani 1 1 d . . . . .
H13 H 0.809158 0.220647 0.360057 0.027 Uiso 1 1 calc R U . . .
C14 C 0.81726(18) 0.16385(13) 0.52805(11) 0.0256(3) Uani 1 1 d . . . . .
H14 H 0.947304 0.109027 0.532184 0.031 Uiso 1 1 calc R U . . .
C15 C 0.71064(19) 0.17592(14) 0.62407(10) 0.0273(3) Uani 1 1 d . . . . .
H15 H 0.768355 0.129285 0.693311 0.033 Uiso 1 1 calc R U . . .
C16 C 0.52012(18) 0.25549(14) 0.62033(10) 0.0258(3) Uani 1 1 d . . . . .
H16 H 0.445134 0.262215 0.686173 0.031 Uiso 1 1 calc R U . . .
C21 C 0.49071(17) 0.53108(13) 0.23696(10) 0.0210(2) Uani 1 1 d . . . . .
C22 C 0.36452(17) 0.65073(13) 0.16723(10) 0.0248(3) Uani 1 1 d . . . . .
H22 H 0.231938 0.652093 0.173960 0.030 Uiso 1 1 calc R U . . .
C23 C 0.42804(19) 0.76727(14) 0.08864(11) 0.0283(3) Uani 1 1 d . . . . .
H23 H 0.340948 0.847363 0.041518 0.034 Uiso 1 1 calc R U . . .
C24 C 0.62016(19) 0.76409(13) 0.08056(11) 0.0289(3) Uani 1 1 d . . . . .
C25 C 0.74891(18) 0.65089(14) 0.14852(11) 0.0288(3) Uani 1 1 d . . . . .
H25 H 0.880446 0.652044 0.142342 0.035 Uiso 1 1 calc R U . . .
C26 C 0.68357(17) 0.53475(13) 0.22638(10) 0.0247(3) Uani 1 1 d . . . . .
H26 H 0.771983 0.455920 0.273581 0.030 Uiso 1 1 calc R U . . .
C31 C 0.57221(17) 0.21510(13) 0.22998(10) 0.0232(3) Uani 1 1 d . . . . .
C32 C 0.68756(18) 0.28576(14) 0.14004(10) 0.0268(3) Uani 1 1 d . . . . .
H32 H 0.644664 0.386387 0.101566 0.032 Uiso 1 1 calc R U . . .
C33 C 0.86346(19) 0.21179(16) 0.10589(11) 0.0335(3) Uani 1 1 d . . . . .
H33 H 0.941274 0.262582 0.046097 0.040 Uiso 1 1 calc R U . . .
C34 C 0.9263(2) 0.06463(17) 0.15828(13) 0.0382(3) Uani 1 1 d . . . . .
H34 H 1.046355 0.013902 0.134506 0.046 Uiso 1 1 calc R U . . .
C35 C 0.8122(2) -0.00766(16) 0.24570(13) 0.0383(3) Uani 1 1 d . . . . .
H35 H 0.853009 -0.108975 0.281410 0.046 Uiso 1 1 calc R U . . .
C36 C 0.63832(19) 0.06684(14) 0.28165(12) 0.0307(3) Uani 1 1 d . . . . .
H36 H 0.562842 0.015670 0.342763 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F C24 1.3565(15) . ?
O C1 1.2299(15) . ?
N C1 1.3518(16) . ?
N C11 1.4018(15) . ?
C1 C2 1.5666(15) . ?
C2 C12 1.5281(16) . ?
C2 C21 1.5387(16) . ?
C2 C3 1.6089(16) . ?
C3 C4 1.5343(17) . ?
C3 C31 1.5346(16) . ?
C3 C5 1.5378(17) . ?
C11 C16 1.3780(17) . ?
C11 C12 1.3959(16) . ?
C12 C13 1.3893(16) . ?
C13 C14 1.3949(17) . ?
C14 C15 1.3844(18) . ?
C15 C16 1.3898(18) . ?
C21 C26 1.3968(17) . ?
C21 C22 1.4007(17) . ?
C22 C23 1.3868(18) . ?
C23 C24 1.3756(19) . ?
C24 C25 1.3723(19) . ?
C25 C26 1.3871(18) . ?
C31 C36 1.3935(18) . ?
C31 C32 1.3980(17) . ?
C32 C33 1.3872(18) . ?
C33 C34 1.383(2) . ?
C34 C35 1.382(2) . ?
C35 C36 1.3887(19) . ?

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 N C11 112.15(10) . . ?
O C1 N 124.28(11) . . ?
O C1 C2 127.26(11) . . ?
N C1 C2 108.46(10) . . ?
C12 C2 C21 112.83(9) . . ?
C12 C2 C1 100.60(9) . . ?
C21 C2 C1 108.68(9) . . ?
C12 C2 C3 110.85(9) . . ?
C21 C2 C3 114.08(9) . . ?
C1 C2 C3 108.87(9) . . ?
C4 C3 C31 111.33(10) . . ?
C4 C3 C5 106.99(10) . . ?
C31 C3 C5 108.15(10) . . ?
C4 C3 C2 107.68(10) . . ?
C31 C3 C2 110.00(9) . . ?
C5 C3 C2 112.69(10) . . ?
C16 C11 C12 123.04(11) . . ?
C16 C11 N 127.31(11) . . ?
C12 C11 N 109.63(10) . . ?
C13 C12 C11 118.43(11) . . ?
C13 C12 C2 132.43(11) . . ?
C11 C12 C2 109.14(10) . . ?
C12 C13 C14 119.32(11) . . ?
C15 C14 C13 120.81(11) . . ?
C14 C15 C16 120.75(12) . . ?
C11 C16 C15 117.62(11) . . ?
C26 C21 C22 117.38(11) . . ?
C26 C21 C2 121.54(10) . . ?
C22 C21 C2 121.08(10) . . ?
C23 C22 C21 121.73(11) . . ?
C24 C23 C22 118.41(12) . . ?
F C24 C25 118.88(12) . . ?
F C24 C23 118.96(12) . . ?
C25 C24 C23 122.15(12) . . ?
C24 C25 C26 118.81(12) . . ?
C25 C26 C21 121.49(11) . . ?
C36 C31 C32 117.30(11) . . ?
C36 C31 C3 122.12(11) . . ?
C32 C31 C3 120.58(11) . . ?
C33 C32 C31 121.28(12) . . ?
C34 C33 C32 120.47(13) . . ?
C35 C34 C33 119.11(13) . . ?
C34 C35 C36 120.42(14) . . ?
C35 C36 C31 121.39(13) . . ?

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
C11 N C1 O 177.92(12) . . . . ?
C11 N C1 C2 -1.20(14) . . . . ?
O C1 C2 C12 -177.65(12) . . . . ?
N C1 C2 C12 1.44(12) . . . . ?
O C1 C2 C21 63.67(15) . . . . ?
N C1 C2 C21 -117.24(11) . . . . ?
O C1 C2 C3 -61.13(16) . . . . ?
N C1 C2 C3 117.96(11) . . . . ?
C12 C2 C3 C4 64.35(12) . . . . ?
C21 C2 C3 C4 -166.97(10) . . . . ?
C1 C2 C3 C4 -45.41(12) . . . . ?
C12 C2 C3 C31 -57.13(12) . . . . ?
C21 C2 C3 C31 71.55(12) . . . . ?
C1 C2 C3 C31 -166.89(10) . . . . ?
C12 C2 C3 C5 -177.90(10) . . . . ?
C21 C2 C3 C5 -49.22(13) . . . . ?
C1 C2 C3 C5 72.34(12) . . . . ?
C1 N C11 C16 -178.13(12) . . . . ?
C1 N C11 C12 0.39(14) . . . . ?
C16 C11 C12 C13 -0.46(18) . . . . ?
N C11 C12 C13 -179.05(10) . . . . ?
C16 C11 C12 C2 179.22(11) . . . . ?
N C11 C12 C2 0.62(13) . . . . ?
C21 C2 C12 C13 -66.00(16) . . . . ?
C1 C2 C12 C13 178.39(12) . . . . ?
C3 C2 C12 C13 63.35(16) . . . . ?
C21 C2 C12 C11 114.39(11) . . . . ?
C1 C2 C12 C11 -1.22(12) . . . . ?
C3 C2 C12 C11 -116.26(10) . . . . ?
C11 C12 C13 C14 -1.22(17) . . . . ?
C2 C12 C13 C14 179.20(12) . . . . ?
C12 C13 C14 C15 1.46(18) . . . . ?
C13 C14 C15 C16 0.00(19) . . . . ?
C12 C11 C16 C15 1.87(19) . . . . ?
N C11 C16 C15 -179.80(12) . . . . ?
C14 C15 C16 C11 -1.61(19) . . . . ?
C12 C2 C21 C26 23.34(15) . . . . ?
C1 C2 C21 C26 134.01(11) . . . . ?
C3 C2 C21 C26 -104.33(13) . . . . ?
C12 C2 C21 C22 -156.27(11) . . . . ?
C1 C2 C21 C22 -45.60(14) . . . . ?
C3 C2 C21 C22 76.07(13) . . . . ?
C26 C21 C22 C23 1.54(18) . . . . ?
C2 C21 C22 C23 -178.83(11) . . . . ?
C21 C22 C23 C24 -0.50(19) . . . . ?
C22 C23 C24 F 179.53(11) . . . . ?
C22 C23 C24 C25 -1.0(2) . . . . ?
F C24 C25 C26 -179.22(12) . . . . ?
C23 C24 C25 C26 1.3(2) . . . . ?
C24 C25 C26 C21 -0.1(2) . . . . ?
C22 C21 C26 C25 -1.22(18) . . . . ?
C2 C21 C26 C25 179.16(11) . . . . ?
C4 C3 C31 C36 -7.09(16) . . . . ?
C5 C3 C31 C36 -124.36(13) . . . . ?
C2 C3 C31 C36 112.18(13) . . . . ?
C4 C3 C31 C32 172.25(11) . . . . ?
C5 C3 C31 C32 54.99(14) . . . . ?
C2 C3 C31 C32 -68.47(14) . . . . ?
C36 C31 C32 C33 -1.92(18) . . . . ?
C3 C31 C32 C33 178.70(11) . . . . ?
C31 C32 C33 C34 2.0(2) . . . . ?
C32 C33 C34 C35 -0.5(2) . . . . ?
C33 C34 C35 C36 -1.1(2) . . . . ?
C34 C35 C36 C31 1.2(2) . . . . ?
C32 C31 C36 C35 0.33(19) . . . . ?
C3 C31 C36 C35 179.70(12) . . . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_zhk001
_database_code_depnum_ccdc_archive 'CCDC 1997425'
loop_
_audit_author_name
_audit_author_address
JD
;SCU
China
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2022-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 Cl N O, C H2 Cl2'
_chemical_formula_sum            'C24 H22 Cl3 N O'
_chemical_formula_weight         446.77

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   10.4147(4)
_cell_length_b                   10.9205(3)
_cell_length_c                   10.9542(4)
_cell_angle_alpha                84.656(2)
_cell_angle_beta                 63.300(2)
_cell_angle_gamma                85.811(2)
_cell_volume                     1107.50(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    7588
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      26.43

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.179
_exptl_absorpt_coefficient_mu    0.429
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9217
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23390
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.709
_diffrn_reflns_theta_max         26.439
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4421
_reflns_number_gt                3396
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0096P)²+1.3841P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4421
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0812
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_restrained_S_all      1.231
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.72325(9) 0.98953(7) 0.07166(9) 0.0320(2) Uani 1 1 d . . . . .
O O 0.3704(2) 0.60571(18) 0.4601(2) 0.0244(5) Uani 1 1 d . . . . .
N N 0.6113(3) 0.6147(2) 0.3960(3) 0.0218(6) Uani 1 1 d . . . . .
H1 H 0.619(3) 0.554(3) 0.445(3) 0.021(8) Uiso 1 1 d . . . . .
C1 C 0.7256(3) 0.6873(3) 0.3073(3) 0.0201(7) Uani 1 1 d . . . . .
C2 C 0.8630(3) 0.6793(3) 0.2955(3) 0.0273(7) Uani 1 1 d . . . . .
H2 H 0.891696 0.616756 0.345354 0.033 Uiso 1 1 calc R U . . .
C3 C 0.9579(3) 0.7666(3) 0.2075(4) 0.0329(8) Uani 1 1 d . . . . .
H3 H 1.054748 0.762453 0.194267 0.040 Uiso 1 1 calc R U . . .
C4 C 0.9136(3) 0.8593(3) 0.1392(3) 0.0295(8) Uani 1 1 d . . . . .
H4 H 0.978736 0.920344 0.082140 0.035 Uiso 1 1 calc R U . . .
C5 C 0.7735(3) 0.8636(2) 0.1534(3) 0.0210(7) Uani 1 1 d . . . . .
C6 C 0.6777(3) 0.7748(2) 0.2342(3) 0.0170(6) Uani 1 1 d . . . . .
C11 C 0.4884(3) 0.6497(3) 0.3886(3) 0.0194(6) Uani 1 1 d . . . . .
C12 C 0.5209(3) 0.7513(2) 0.2708(3) 0.0179(6) Uani 1 1 d . . . . .
C13 C 0.4234(3) 0.8646(3) 0.3290(3) 0.0210(7) Uani 1 1 d . . . . .
C14 C 0.3919(4) 0.8905(3) 0.4613(3) 0.0305(8) Uani 1 1 d . . . . .
H14 H 0.428730 0.836604 0.512233 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3082(4) 0.9928(3) 0.5211(4) 0.0412(9) Uani 1 1 d . . . . .
H15 H 0.287909 1.008136 0.612115 0.049 Uiso 1 1 calc R U . . .
C16 C 0.2543(4) 1.0724(3) 0.4486(4) 0.0441(10) Uani 1 1 d . . . . .
H16 H 0.195846 1.142160 0.489468 0.053 Uiso 1 1 calc R U . . .
C17 C 0.2858(4) 1.0496(3) 0.3173(4) 0.0435(10) Uani 1 1 d . . . . .
H17 H 0.250057 1.104637 0.266415 0.052 Uiso 1 1 calc R U . . .
C18 C 0.3697(4) 0.9468(3) 0.2574(4) 0.0325(8) Uani 1 1 d . . . . .
H18 H 0.390557 0.932559 0.165954 0.039 Uiso 1 1 calc R U . . .
C21 C 0.5069(3) 0.6833(3) 0.1522(3) 0.0223(7) Uani 1 1 d . . . . .
C22 C 0.5795(4) 0.7529(3) 0.0107(3) 0.0295(8) Uani 1 1 d . . . . .
H22A H 0.679010 0.768963 -0.010541 0.044 Uiso 1 1 calc R U . . .
H22B H 0.526878 0.831197 0.011386 0.044 Uiso 1 1 calc R U . . .
H22C H 0.579005 0.703034 -0.058938 0.044 Uiso 1 1 calc R U . . .
C23 C 0.3471(3) 0.6711(3) 0.1880(4) 0.0312(8) Uani 1 1 d . . . . .
H23A H 0.295139 0.638668 0.283360 0.047 Uiso 1 1 calc R U . . .
H23B H 0.339083 0.614749 0.127350 0.047 Uiso 1 1 calc R U . . .
H23C H 0.305543 0.752082 0.176068 0.047 Uiso 1 1 calc R U . . .
C24 C 0.5820(3) 0.5544(3) 0.1433(3) 0.0256(7) Uani 1 1 d . . . . .
C25 C 0.7303(4) 0.5392(3) 0.0706(4) 0.0313(8) Uani 1 1 d . . . . .
H25 H 0.785800 0.608426 0.021655 0.038 Uiso 1 1 calc R U . . .
C26 C 0.7994(4) 0.4248(3) 0.0678(4) 0.0433(10) Uani 1 1 d . . . . .
H26 H 0.901023 0.416666 0.017375 0.052 Uiso 1 1 calc R U . . .
C27 C 0.7210(5) 0.3235(3) 0.1379(4) 0.0470(11) Uani 1 1 d . . . . .
H27 H 0.768233 0.245547 0.137126 0.056 Uiso 1 1 calc R U . . .
C28 C 0.5742(4) 0.3355(3) 0.2088(4) 0.0417(10) Uani 1 1 d . . . . .
H28 H 0.519636 0.265515 0.256456 0.050 Uiso 1 1 calc R U . . .
C29 C 0.5048(4) 0.4497(3) 0.2112(4) 0.0324(8) Uani 1 1 d . . . . .
H29 H 0.402973 0.456515 0.260102 0.039 Uiso 1 1 calc R U . . .
Cl1S Cl -0.05109(15) 0.63354(11) 0.62481(17) 0.0829(4) Uani 1 1 d . . . . .
Cl2S Cl -0.00542(11) 0.80830(12) 0.78402(12) 0.0638(3) Uani 1 1 d . . . . .
C1S C 0.0632(5) 0.7407(5) 0.6289(6) 0.0863(18) Uani 1 1 d . . . . .
H1SA H 0.157020 0.699209 0.611338 0.104 Uiso 1 1 calc R U . . .
H1SB H 0.080033 0.805718 0.554583 0.104 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl C5 1.747(3) . ?
O C11 1.227(3) . ?
N C11 1.344(4) . ?
N C1 1.395(4) . ?
C1 C2 1.374(4) . ?
C1 C6 1.396(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.378(4) . ?
C4 C5 1.394(4) . ?
C5 C6 1.380(4) . ?
C6 C12 1.533(4) . ?
C11 C12 1.552(4) . ?
C12 C13 1.533(4) . ?
C12 C21 1.621(4) . ?
C13 C18 1.387(4) . ?
C13 C14 1.387(4) . ?
C14 C15 1.385(5) . ?
C15 C16 1.379(5) . ?
C16 C17 1.367(5) . ?
C17 C18 1.391(5) . ?
C21 C22 1.538(4) . ?
C21 C23 1.542(4) . ?
C21 C24 1.548(4) . ?
C24 C25 1.389(4) . ?
C24 C29 1.395(4) . ?
C25 C26 1.391(5) . ?
C26 C27 1.375(5) . ?
C27 C28 1.371(5) . ?
C28 C29 1.391(5) . ?
Cl1S C1S 1.746(5) . ?
Cl2S C1S 1.735(5) . ?

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
C11 N C1 112.2(2) . . ?
C2 C1 N 126.5(3) . . ?
C2 C1 C6 124.3(3) . . ?
N C1 C6 109.2(2) . . ?
C1 C2 C3 117.1(3) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C5 120.2(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 Cl 122.0(2) . . ?
C4 C5 Cl 117.0(2) . . ?
C5 C6 C1 116.5(3) . . ?
C5 C6 C12 134.4(3) . . ?
C1 C6 C12 109.0(2) . . ?
O C11 N 125.7(3) . . ?
O C11 C12 125.3(3) . . ?
N C11 C12 109.0(2) . . ?
C6 C12 C13 111.1(2) . . ?
C6 C12 C11 100.0(2) . . ?
C13 C12 C11 108.6(2) . . ?
C6 C12 C21 112.0(2) . . ?
C13 C12 C21 118.9(2) . . ?
C11 C12 C21 104.2(2) . . ?
C18 C13 C14 117.3(3) . . ?
C18 C13 C12 125.0(3) . . ?
C14 C13 C12 117.6(3) . . ?
C15 C14 C13 121.7(3) . . ?
C16 C15 C14 120.0(3) . . ?
C17 C16 C15 119.2(3) . . ?
C16 C17 C18 120.8(3) . . ?
C13 C18 C17 121.0(3) . . ?
C22 C21 C23 107.9(2) . . ?
C22 C21 C24 108.2(3) . . ?
C23 C21 C24 110.3(2) . . ?
C22 C21 C12 112.8(2) . . ?
C23 C21 C12 110.1(2) . . ?
C24 C21 C12 107.6(2) . . ?
C25 C24 C29 117.2(3) . . ?
C25 C24 C21 121.1(3) . . ?
C29 C24 C21 121.7(3) . . ?
C24 C25 C26 121.5(3) . . ?
C27 C26 C25 120.1(4) . . ?
C28 C27 C26 119.6(3) . . ?
C27 C28 C29 120.3(3) . . ?
C28 C29 C24 121.2(3) . . ?
Cl2S C1S Cl1S 112.8(3) . . ?

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
C11 N C1 C2 176.5(3) . . . . ?
C11 N C1 C6 -1.1(3) . . . . ?
N C1 C2 C3 -175.4(3) . . . . ?
C6 C1 C2 C3 1.8(5) . . . . ?
C1 C2 C3 C4 2.1(5) . . . . ?
C2 C3 C4 C5 -2.6(5) . . . . ?
C3 C4 C5 C6 -1.0(5) . . . . ?
C3 C4 C5 Cl 176.1(3) . . . . ?
C4 C5 C6 C1 4.6(4) . . . . ?
Cl C5 C6 C1 -172.4(2) . . . . ?
C4 C5 C6 C12 -179.4(3) . . . . ?
Cl C5 C6 C12 3.7(5) . . . . ?
C2 C1 C6 C5 -5.1(4) . . . . ?
N C1 C6 C5 172.6(3) . . . . ?
C2 C1 C6 C12 177.8(3) . . . . ?
N C1 C6 C12 -4.5(3) . . . . ?
C1 N C11 O -176.2(3) . . . . ?
C1 N C11 C12 6.1(3) . . . . ?
C5 C6 C12 C13 -54.4(4) . . . . ?
C1 C6 C12 C13 121.9(3) . . . . ?
C5 C6 C12 C11 -168.9(3) . . . . ?
C1 C6 C12 C11 7.4(3) . . . . ?
C5 C6 C12 C21 81.3(4) . . . . ?
C1 C6 C12 C21 -102.4(3) . . . . ?
O C11 C12 C6 174.2(3) . . . . ?
N C11 C12 C6 -8.0(3) . . . . ?
O C11 C12 C13 57.8(4) . . . . ?
N C11 C12 C13 -124.5(3) . . . . ?
O C11 C12 C21 -69.9(3) . . . . ?
N C11 C12 C21 107.8(3) . . . . ?
C6 C12 C13 C18 102.8(3) . . . . ?
C11 C12 C13 C18 -148.2(3) . . . . ?
C21 C12 C13 C18 -29.4(4) . . . . ?
C6 C12 C13 C14 -74.0(3) . . . . ?
C11 C12 C13 C14 35.1(3) . . . . ?
C21 C12 C13 C14 153.8(3) . . . . ?
C18 C13 C14 C15 1.1(5) . . . . ?
C12 C13 C14 C15 178.1(3) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
C14 C15 C16 C17 -0.7(6) . . . . ?
C15 C16 C17 C18 0.8(6) . . . . ?
C14 C13 C18 C17 -1.0(5) . . . . ?
C12 C13 C18 C17 -177.8(3) . . . . ?
C16 C17 C18 C13 0.1(6) . . . . ?
C6 C12 C21 C22 -54.9(3) . . . . ?
C13 C12 C21 C22 77.0(3) . . . . ?
C11 C12 C21 C22 -162.0(2) . . . . ?
C6 C12 C21 C23 -175.4(2) . . . . ?
C13 C12 C21 C23 -43.6(3) . . . . ?
C11 C12 C21 C23 77.4(3) . . . . ?
C6 C12 C21 C24 64.4(3) . . . . ?
C13 C12 C21 C24 -163.8(2) . . . . ?
C11 C12 C21 C24 -42.8(3) . . . . ?
C22 C21 C24 C25 40.7(4) . . . . ?
C23 C21 C24 C25 158.5(3) . . . . ?
C12 C21 C24 C25 -81.4(3) . . . . ?
C22 C21 C24 C29 -141.5(3) . . . . ?
C23 C21 C24 C29 -23.7(4) . . . . ?
C12 C21 C24 C29 96.4(3) . . . . ?
C29 C24 C25 C26 -1.2(5) . . . . ?
C21 C24 C25 C26 176.7(3) . . . . ?
C24 C25 C26 C27 0.0(5) . . . . ?
C25 C26 C27 C28 0.9(6) . . . . ?
C26 C27 C28 C29 -0.7(6) . . . . ?
C27 C28 C29 C24 -0.6(5) . . . . ?
C25 C24 C29 C28 1.5(5) . . . . ?
C21 C24 C29 C28 -176.4(3) . . . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.062

