# Supplementary Information (SI) 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_1
_database_code_depnum_ccdc_archive 'CCDC 2361518'
loop_
_audit_author_name
_audit_author_address
'Chun-Hua Yang'
;Anyang Normal University
China
;
_audit_update_record             
;
2024-06-10 deposited with the CCDC.	2024-09-27 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         ?
_chemical_formula_sum            'C17 H14 Cl N O'
_chemical_formula_weight         283.74

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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6809(3)
_cell_length_b                   6.2345(2)
_cell_length_c                   23.1731(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.7841(14)
_cell_angle_gamma                90
_cell_volume                     1395.58(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9925
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.15

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.268
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48680
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.231
_diffrn_reflns_theta_max         28.335
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3470
_reflns_number_gt                2767
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0695P)²+0.2065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3470
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.19950(4) 0.89852(7) 0.18286(2) 0.07747(19) Uani 1 1 d . . . . .
O1 O -0.14998(14) 0.87643(17) 0.02332(5) 0.0680(3) Uani 1 1 d . . . . .
N1 N -0.12270(12) 0.53223(18) 0.05400(5) 0.0486(3) Uani 1 1 d . . . . .
C8 C -0.00008(13) 0.5930(2) 0.17956(6) 0.0457(3) Uani 1 1 d . . . . .
C3 C -0.05485(14) 0.4076(2) 0.15241(6) 0.0457(3) Uani 1 1 d . . . . .
C9 C 0.06671(13) 0.7557(2) 0.14495(7) 0.0498(3) Uani 1 1 d . . . . .
C1 C -0.08606(15) 0.7407(2) 0.05310(6) 0.0504(3) Uani 1 1 d . . . . .
C2 C -0.04180(16) 0.3758(2) 0.08892(6) 0.0508(3) Uani 1 1 d . . . . .
H2A H 0.054835 0.387728 0.080676 0.061 Uiso 1 1 calc R U . . .
H2B H -0.072821 0.232370 0.078224 0.061 Uiso 1 1 calc R U . . .
C12 C -0.36685(15) 0.4126(2) 0.05674(6) 0.0465(3) Uani 1 1 d . . . . .
C10 C 0.03708(15) 0.8096(2) 0.09007(7) 0.0528(3) Uani 1 1 d . . . . .
H10A H 0.099622 0.899320 0.073140 0.063 Uiso 1 1 calc R U . . .
C4 C -0.11723(16) 0.2540(2) 0.18523(7) 0.0579(4) Uani 1 1 d . . . . .
H4A H -0.154368 0.131322 0.167425 0.070 Uiso 1 1 calc R U . . .
C13 C -0.41865(18) 0.5706(2) 0.09112(7) 0.0600(4) Uani 1 1 d . . . . .
H13A H -0.375801 0.704147 0.093375 0.072 Uiso 1 1 calc R U . . .
C7 C -0.00962(15) 0.6176(3) 0.23883(7) 0.0565(4) Uani 1 1 d . . . . .
H7A H 0.026245 0.740079 0.257183 0.068 Uiso 1 1 calc R U . . .
C11 C -0.24671(17) 0.4569(3) 0.02061(6) 0.0552(4) Uani 1 1 d . . . . .
H11A H -0.224227 0.326704 0.000334 0.066 Uiso 1 1 calc R U . . .
H11B H -0.274301 0.564163 -0.008220 0.066 Uiso 1 1 calc R U . . .
C17 C -0.43189(17) 0.2151(2) 0.05470(7) 0.0573(4) Uani 1 1 d . . . . .
H17A H -0.397554 0.105567 0.032450 0.069 Uiso 1 1 calc R U . . .
C6 C -0.07170(18) 0.4623(3) 0.27062(7) 0.0659(4) Uani 1 1 d . . . . .
H6A H -0.077473 0.480713 0.310218 0.079 Uiso 1 1 calc R U . . .
C15 C -0.59825(17) 0.3371(3) 0.11899(7) 0.0642(4) Uani 1 1 d . . . . .
H15A H -0.676119 0.312578 0.139498 0.077 Uiso 1 1 calc R U . . .
C5 C -0.12490(18) 0.2812(3) 0.24420(8) 0.0671(4) Uani 1 1 d . . . . .
H5A H -0.166176 0.176461 0.265876 0.081 Uiso 1 1 calc R U . . .
C16 C -0.54739(19) 0.1784(3) 0.08535(8) 0.0664(4) Uani 1 1 d . . . . .
H16A H -0.590832 0.045350 0.083128 0.080 Uiso 1 1 calc R U . . .
C14 C -0.53287(19) 0.5331(3) 0.12209(8) 0.0667(4) Uani 1 1 d . . . . .
H14A H -0.565998 0.640871 0.145231 0.080 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
Cl1 C9 1.7516(14) . ?
O1 C1 1.2323(18) . ?
N1 C1 1.3480(18) . ?
N1 C2 1.4616(18) . ?
N1 C11 1.4621(19) . ?
C8 C7 1.391(2) . ?
C8 C3 1.4034(18) . ?
C8 C9 1.4690(19) . ?
C3 C4 1.386(2) . ?
C3 C2 1.498(2) . ?
C9 C10 1.328(2) . ?
C1 C10 1.485(2) . ?
C12 C13 1.382(2) . ?
C12 C17 1.3825(19) . ?
C12 C11 1.503(2) . ?
C4 C5 1.384(2) . ?
C13 C14 1.377(3) . ?
C7 C6 1.378(2) . ?
C17 C16 1.383(2) . ?
C6 C5 1.369(3) . ?
C15 C16 1.371(3) . ?
C15 C14 1.375(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 N1 C2 121.35(12) . . ?
C1 N1 C11 120.61(12) . . ?
C2 N1 C11 118.03(11) . . ?
C7 C8 C3 119.05(13) . . ?
C7 C8 C9 121.54(12) . . ?
C3 C8 C9 119.41(12) . . ?
C4 C3 C8 119.25(14) . . ?
C4 C3 C2 121.04(12) . . ?
C8 C3 C2 119.69(12) . . ?
C10 C9 C8 128.48(13) . . ?
C10 C9 Cl1 117.15(11) . . ?
C8 C9 Cl1 114.35(11) . . ?
O1 C1 N1 123.21(14) . . ?
O1 C1 C10 118.62(13) . . ?
N1 C1 C10 118.17(12) . . ?
N1 C2 C3 112.25(11) . . ?
C13 C12 C17 118.24(14) . . ?
C13 C12 C11 120.90(13) . . ?
C17 C12 C11 120.81(13) . . ?
C9 C10 C1 126.42(13) . . ?
C3 C4 C5 120.73(15) . . ?
C14 C13 C12 120.89(14) . . ?
C6 C7 C8 120.66(14) . . ?
N1 C11 C12 113.75(11) . . ?
C16 C17 C12 120.76(15) . . ?
C5 C6 C7 120.32(15) . . ?
C16 C15 C14 119.30(16) . . ?
C6 C5 C4 119.98(16) . . ?
C15 C16 C17 120.38(15) . . ?
C15 C14 C13 120.41(16) . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.046



####################################################################### 
# 
# 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_2024031603YZT_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2361520'
loop_
_audit_author_name
_audit_author_address
'Chun-Hua Yang'
;Anyang Normal University
China
;
_audit_update_record             
;
2024-06-10 deposited with the CCDC.	2024-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 Cl F N O'
_chemical_formula_weight         377.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.9521(12)
_cell_length_b                   6.7931(5)
_cell_length_c                   18.8317(16)
_cell_angle_alpha                90
_cell_angle_beta                 95.218(5)
_cell_angle_gamma                90
_cell_volume                     1904.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    8119
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.10

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.519
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.222
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12683
_diffrn_reflns_av_unetI/netI     0.1240
_diffrn_reflns_av_R_equivalents  0.1202
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.172
_diffrn_reflns_theta_max         28.338
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             4306
_reflns_number_gt                1842
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0620P)²+0.3800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4306
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1627
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.2036
_refine_ls_wR_factor_gt          0.1388
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.44481(7) 0.96579(13) 0.59506(6) 0.0616(3) Uani 1 1 d . . . . .
O1 O 0.6310(2) 0.8533(3) 0.55439(14) 0.0631(8) Uani 1 1 d . . . . .
N1 N 0.6226(2) 0.5211(4) 0.54762(16) 0.0504(8) Uani 1 1 d . . . . .
F1 F 0.2736(2) 0.7008(5) 0.88230(17) 0.1192(12) Uani 1 1 d . . . . .
C7 C 0.4862(3) 0.7889(4) 0.6563(2) 0.0477(9) Uani 1 1 d . . . . .
C8 C 0.5569(3) 0.6794(5) 0.64394(19) 0.0465(9) Uani 1 1 d . . . . .
C9 C 0.5930(3) 0.5210(5) 0.69251(19) 0.0476(9) Uani 1 1 d . . . . .
C14 C 0.6132(3) 0.3457(5) 0.6599(2) 0.0497(9) Uani 1 1 d . . . . .
C15 C 0.5951(3) 0.3359(5) 0.58037(19) 0.0549(10) Uani 1 1 d . . . . .
H15A H 0.627982 0.226647 0.562190 0.066 Uiso 1 1 calc R U . . .
H15B H 0.531533 0.313580 0.567762 0.066 Uiso 1 1 calc R U . . .
C10 C 0.6111(3) 0.5415(6) 0.7662(2) 0.0594(11) Uani 1 1 d . . . . .
H10A H 0.599201 0.659590 0.788465 0.071 Uiso 1 1 calc R U . . .
C6 C 0.4308(3) 0.7673(5) 0.7168(2) 0.0497(9) Uani 1 1 d . . . . .
C16 C 0.6058(3) 0.6956(5) 0.5778(2) 0.0495(9) Uani 1 1 d . . . . .
C18 C 0.7633(3) 0.4228(5) 0.5015(2) 0.0553(10) Uani 1 1 d . . . . .
C17 C 0.6715(3) 0.5068(5) 0.4842(2) 0.0568(10) Uani 1 1 d . . . . .
H17A H 0.676502 0.636642 0.463567 0.068 Uiso 1 1 calc R U . . .
H17B H 0.638159 0.423887 0.449195 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6488(3) 0.1888(5) 0.7005(2) 0.0614(11) Uani 1 1 d . . . . .
H13A H 0.661342 0.070424 0.678714 0.074 Uiso 1 1 calc R U . . .
C1 C 0.4186(3) 0.9218(6) 0.7627(2) 0.0645(11) Uani 1 1 d . . . . .
H1A H 0.445905 1.042263 0.755554 0.077 Uiso 1 1 calc R U . . .
C5 C 0.3885(3) 0.5900(6) 0.7284(2) 0.0631(11) Uani 1 1 d . . . . .
H5A H 0.395662 0.484726 0.697861 0.076 Uiso 1 1 calc R U . . .
C11 C 0.6466(3) 0.3851(6) 0.8052(2) 0.0723(13) Uani 1 1 d . . . . .
H11A H 0.658324 0.397610 0.854373 0.087 Uiso 1 1 calc R U . . .
C12 C 0.6653(3) 0.2098(6) 0.7729(3) 0.0725(13) Uani 1 1 d . . . . .
H12A H 0.689258 0.105243 0.800325 0.087 Uiso 1 1 calc R U . . .
C4 C 0.3362(3) 0.5667(7) 0.7843(2) 0.0748(13) Uani 1 1 d . . . . .
H4A H 0.308517 0.447002 0.792026 0.090 Uiso 1 1 calc R U . . .
C2 C 0.3661(3) 0.8995(7) 0.8191(2) 0.0742(13) Uani 1 1 d . . . . .
H2A H 0.358482 1.003282 0.850204 0.089 Uiso 1 1 calc R U . . .
C3 C 0.3261(3) 0.7228(8) 0.8281(3) 0.0762(13) Uani 1 1 d . . . . .
C23 C 0.7840(3) 0.2357(6) 0.4806(3) 0.0824(15) Uani 1 1 d . . . . .
H23A H 0.741376 0.161335 0.453412 0.099 Uiso 1 1 calc R U . . .
C19 C 0.8284(4) 0.5290(8) 0.5400(3) 0.0838(15) Uani 1 1 d . . . . .
H19A H 0.815688 0.657109 0.553310 0.101 Uiso 1 1 calc R U . . .
C22 C 0.8685(4) 0.1577(9) 0.5000(4) 0.113(2) Uani 1 1 d . . . . .
H22A H 0.882198 0.030873 0.485881 0.136 Uiso 1 1 calc R U . . .
C20 C 0.9117(4) 0.4531(11) 0.5596(3) 0.115(2) Uani 1 1 d . . . . .
H20A H 0.954726 0.527588 0.586357 0.138 Uiso 1 1 calc R U . . .
C21 C 0.9306(5) 0.2650(11) 0.5391(4) 0.119(2) Uani 1 1 d . . . . .
H21A H 0.986802 0.211062 0.552321 0.143 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
Cl1 C7 1.741(3) . ?
O1 C16 1.231(4) . ?
N1 C16 1.349(4) . ?
N1 C17 1.458(5) . ?
N1 C15 1.476(4) . ?
F1 C3 1.352(5) . ?
C7 C8 1.330(5) . ?
C7 C6 1.475(5) . ?
C8 C9 1.482(5) . ?
C8 C16 1.504(5) . ?
C9 C14 1.386(5) . ?
C9 C10 1.396(5) . ?
C14 C13 1.389(5) . ?
C14 C15 1.500(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C10 C11 1.372(5) . ?
C10 H10A 0.9300 . ?
C6 C1 1.382(5) . ?
C6 C5 1.387(5) . ?
C18 C19 1.366(6) . ?
C18 C23 1.374(5) . ?
C18 C17 1.496(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C13 C12 1.371(6) . ?
C13 H13A 0.9300 . ?
C1 C2 1.385(6) . ?
C1 H1A 0.9300 . ?
C5 C4 1.376(6) . ?
C5 H5A 0.9300 . ?
C11 C12 1.378(6) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C4 C3 1.360(6) . ?
C4 H4A 0.9300 . ?
C2 C3 1.359(6) . ?
C2 H2A 0.9300 . ?
C23 C22 1.387(7) . ?
C23 H23A 0.9300 . ?
C19 C20 1.367(8) . ?
C19 H19A 0.9300 . ?
C22 C21 1.346(8) . ?
C22 H22A 0.9300 . ?
C20 C21 1.372(8) . ?
C20 H20A 0.9300 . ?
C21 H21A 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
C16 N1 C17 122.0(3) . . ?
C16 N1 C15 120.2(3) . . ?
C17 N1 C15 117.7(3) . . ?
C8 C7 C6 126.3(3) . . ?
C8 C7 Cl1 120.6(3) . . ?
C6 C7 Cl1 112.9(3) . . ?
C7 C8 C9 123.2(3) . . ?
C7 C8 C16 123.9(3) . . ?
C9 C8 C16 112.7(3) . . ?
C14 C9 C10 119.7(3) . . ?
C14 C9 C8 115.6(3) . . ?
C10 C9 C8 124.6(3) . . ?
C9 C14 C13 120.2(4) . . ?
C9 C14 C15 117.0(3) . . ?
C13 C14 C15 122.8(3) . . ?
N1 C15 C14 110.4(3) . . ?
N1 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N1 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C11 C10 C9 119.1(4) . . ?
C11 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
C1 C6 C5 118.2(4) . . ?
C1 C6 C7 121.5(3) . . ?
C5 C6 C7 120.3(3) . . ?
O1 C16 N1 122.6(3) . . ?
O1 C16 C8 123.2(3) . . ?
N1 C16 C8 114.1(3) . . ?
C19 C18 C23 118.2(5) . . ?
C19 C18 C17 120.7(4) . . ?
C23 C18 C17 121.1(4) . . ?
N1 C17 C18 111.5(3) . . ?
N1 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
N1 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C6 C1 C2 120.9(4) . . ?
C6 C1 H1A 119.6 . . ?
C2 C1 H1A 119.6 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C10 C11 C12 121.1(4) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C3 C4 C5 118.4(4) . . ?
C3 C4 H4A 120.8 . . ?
C5 C4 H4A 120.8 . . ?
C3 C2 C1 118.6(4) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
F1 C3 C2 119.0(4) . . ?
F1 C3 C4 118.4(5) . . ?
C2 C3 C4 122.6(4) . . ?
C18 C23 C22 120.1(5) . . ?
C18 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C18 C19 C20 122.1(5) . . ?
C18 C19 H19A 118.9 . . ?
C20 C19 H19A 118.9 . . ?
C21 C22 C23 120.2(6) . . ?
C21 C22 H22A 119.9 . . ?
C23 C22 H22A 119.9 . . ?
C19 C20 C21 118.8(6) . . ?
C19 C20 H20A 120.6 . . ?
C21 C20 H20A 120.6 . . ?
C22 C21 C20 120.6(6) . . ?
C22 C21 H21A 119.7 . . ?
C20 C21 H21A 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C7 C8 C9 -2.8(6) . . . . ?
Cl1 C7 C8 C9 -177.4(3) . . . . ?
C6 C7 C8 C16 174.0(3) . . . . ?
Cl1 C7 C8 C16 -0.6(5) . . . . ?
C7 C8 C9 C14 134.6(4) . . . . ?
C16 C8 C9 C14 -42.5(4) . . . . ?
C7 C8 C9 C10 -48.5(6) . . . . ?
C16 C8 C9 C10 134.4(4) . . . . ?
C10 C9 C14 C13 1.8(6) . . . . ?
C8 C9 C14 C13 178.9(4) . . . . ?
C10 C9 C14 C15 -177.9(4) . . . . ?
C8 C9 C14 C15 -0.8(5) . . . . ?
C16 N1 C15 C14 -41.0(5) . . . . ?
C17 N1 C15 C14 136.3(4) . . . . ?
C9 C14 C15 N1 41.5(5) . . . . ?
C13 C14 C15 N1 -138.2(4) . . . . ?
C14 C9 C10 C11 -1.6(6) . . . . ?
C8 C9 C10 C11 -178.4(4) . . . . ?
C8 C7 C6 C1 123.3(4) . . . . ?
Cl1 C7 C6 C1 -61.7(4) . . . . ?
C8 C7 C6 C5 -57.4(6) . . . . ?
Cl1 C7 C6 C5 117.6(3) . . . . ?
C17 N1 C16 O1 -0.6(6) . . . . ?
C15 N1 C16 O1 176.6(4) . . . . ?
C17 N1 C16 C8 -178.3(3) . . . . ?
C15 N1 C16 C8 -1.1(5) . . . . ?
C7 C8 C16 O1 49.0(6) . . . . ?
C9 C8 C16 O1 -133.9(4) . . . . ?
C7 C8 C16 N1 -133.3(4) . . . . ?
C9 C8 C16 N1 43.8(4) . . . . ?
C16 N1 C17 C18 108.7(4) . . . . ?
C15 N1 C17 C18 -68.6(4) . . . . ?
C19 C18 C17 N1 -70.3(5) . . . . ?
C23 C18 C17 N1 108.3(4) . . . . ?
C9 C14 C13 C12 -1.1(6) . . . . ?
C15 C14 C13 C12 178.6(4) . . . . ?
C5 C6 C1 C2 0.5(6) . . . . ?
C7 C6 C1 C2 179.9(4) . . . . ?
C1 C6 C5 C4 -0.4(6) . . . . ?
C7 C6 C5 C4 -179.8(4) . . . . ?
C9 C10 C11 C12 0.6(7) . . . . ?
C14 C13 C12 C11 0.1(7) . . . . ?
C10 C11 C12 C13 0.2(7) . . . . ?
C6 C5 C4 C3 0.5(7) . . . . ?
C6 C1 C2 C3 -0.6(7) . . . . ?
C1 C2 C3 F1 -178.9(4) . . . . ?
C1 C2 C3 C4 0.7(8) . . . . ?
C5 C4 C3 F1 179.0(4) . . . . ?
C5 C4 C3 C2 -0.7(8) . . . . ?
C19 C18 C23 C22 1.5(8) . . . . ?
C17 C18 C23 C22 -177.1(5) . . . . ?
C23 C18 C19 C20 -1.8(8) . . . . ?
C17 C18 C19 C20 176.8(5) . . . . ?
C18 C23 C22 C21 -0.3(10) . . . . ?
C18 C19 C20 C21 0.8(10) . . . . ?
C23 C22 C21 C20 -0.7(11) . . . . ?
C19 C20 C21 C22 0.5(11) . . . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.051



