# 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_Pbcn_a
_audit_block_doi                 10.5517/ccdc.csd.cc251dzm
_database_code_depnum_ccdc_archive 'CCDC 1997360'
_audit_update_record             
;
2020-04-29 deposited with the CCDC.	2022-09-05 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 H13 N O2'
_chemical_formula_weight         263.28

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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

_cell_length_a                   26.498(4)
_cell_length_b                   7.3940(10)
_cell_length_c                   6.9959(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1370.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1164
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      20.72

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   ?
_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 SMART APEXII CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7172
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         26.408
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1408
_reflns_number_gt                903
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0693P)²] 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         1408
_refine_ls_number_parameters     157
_refine_ls_number_restraints     133
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
C1 C 0.6080(3) 0.7357(16) 0.3512(17) 0.053(2) Uani 0.5 1 d G U P A -1
C2 C 0.6293(3) 0.8613(13) 0.4752(16) 0.0581(17) Uani 0.5 1 d G U P A -1
H2 H 0.609027 0.947925 0.533476 0.070 Uiso 0.5 1 calc R U P A -1
C3 C 0.6808(3) 0.8574(11) 0.5121(15) 0.0623(17) Uani 0.5 1 d G U P A -1
H3 H 0.695039 0.941393 0.595017 0.075 Uiso 0.5 1 calc R U P A -1
C4 C 0.7111(2) 0.7278(11) 0.4250(14) 0.0617(18) Uani 0.5 1 d G U P A -1
H4 H 0.745572 0.725225 0.449625 0.074 Uiso 0.5 1 calc R U P A -1
C5 C 0.6898(3) 0.6022(12) 0.3010(15) 0.069(2) Uani 0.5 1 d G U P A -1
H5 H 0.710093 0.515587 0.242688 0.083 Uiso 0.5 1 calc R U P A -1
C6 C 0.6383(3) 0.6062(15) 0.2641(16) 0.071(3) Uani 0.5 1 d G U P A -1
H6 H 0.624081 0.522117 0.181145 0.085 Uiso 0.5 1 calc R U P A -1
C7 C 0.5529(6) 0.729(3) 0.276(2) 0.057(2) Uani 0.5 1 d . U P A -1
C8 C 0.5283(6) 0.590(2) 0.272(3) 0.045(2) Uani 0.5 1 d . U P A -1
C9 C 0.5400(6) 0.394(2) 0.286(2) 0.057(2) Uani 0.5 1 d . U P A -1
H9 H 0.571112 0.342423 0.316160 0.069 Uiso 0.5 1 calc R U P A -1
C11 C 0.4773(7) 0.571(2) 0.231(3) 0.050(2) Uani 0.5 1 d D U P A -1
C12 C 0.3921(3) 0.7328(15) 0.1653(17) 0.057(2) Uani 0.5 1 d G U P A -1
C13 C 0.3552(3) 0.6130(13) 0.2276(15) 0.0527(17) Uani 0.5 1 d G U P A -1
H13 H 0.363721 0.518443 0.309102 0.063 Uiso 0.5 1 calc R U P A -1
C14 C 0.3055(3) 0.6344(11) 0.1681(13) 0.0537(15) Uani 0.5 1 d G U P A -1
H14 H 0.280789 0.554257 0.209767 0.064 Uiso 0.5 1 calc R U P A -1
C15 C 0.2927(3) 0.7757(11) 0.0463(14) 0.0644(19) Uani 0.5 1 d G U P A -1
H15 H 0.259475 0.790104 0.006493 0.077 Uiso 0.5 1 calc R U P A -1
C16 C 0.3296(3) 0.8956(11) -0.0160(15) 0.076(2) Uani 0.5 1 d G U P A -1
H16 H 0.321093 0.990141 -0.097448 0.091 Uiso 0.5 1 calc R U P A -1
C17 C 0.3793(3) 0.8741(14) 0.0436(17) 0.072(2) Uani 0.5 1 d G U P A -1
H17 H 0.404025 0.954330 0.001885 0.086 Uiso 0.5 1 calc R U P A -1
C10 C 0.4943(6) 0.2985(4) 0.245(5) 0.063(2) Uani 0.5 1 d D U P A -1
H10 H 0.491441 0.173333 0.238049 0.076 Uiso 0.5 1 calc R U P A -1
N1 N 0.4435(5) 0.734(2) 0.1873(18) 0.056(2) Uani 0.5 1 d . U P A -1
H1 H 0.458268 0.836813 0.175423 0.068 Uiso 0.5 1 calc R U P A -1
O1 O 0.53406(9) 0.8911(3) 0.2553(4) 0.0810(9) Uani 0.5 1 d . U P A -1
O2 O 0.4570(4) 0.4120(15) 0.2178(18) 0.068(2) Uani 0.5 1 d D U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C7 1.553(19) . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C7 C8 1.22(3) . ?
C7 O1 1.30(2) . ?
C8 C11 1.390(6) . ?
C8 C9 1.487(18) . ?
C9 C10 1.43(2) . ?
C11 O2 1.298(16) . ?
C11 N1 1.53(2) . ?
C12 N1 1.370(16) . ?
C12 C13 1.3900 . ?
C12 C17 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C16 C17 1.3900 . ?
C10 O2 1.310(15) . ?

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
C2 C1 C6 120.0 . . ?
C2 C1 C7 127.7(9) . . ?
C6 C1 C7 112.0(9) . . ?
C1 C2 C3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C3 C4 C5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C8 C7 O1 124.7(16) . . ?
C8 C7 C1 122.4(18) . . ?
O1 C7 C1 111.7(14) . . ?
C7 C8 C11 127(2) . . ?
C7 C8 C9 135.4(19) . . ?
C11 C8 C9 96.9(16) . . ?
C10 C9 C8 106.8(13) . . ?
O2 C11 C8 120.5(17) . . ?
O2 C11 N1 117.1(17) . . ?
C8 C11 N1 122.3(18) . . ?
N1 C12 C13 131.9(8) . . ?
N1 C12 C17 107.8(8) . . ?
C13 C12 C17 120.0 . . ?
C14 C13 C12 120.0 . . ?
C13 C14 C15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C16 C17 C12 120.0 . . ?
O2 C10 C9 110.7(3) . . ?
C12 N1 C11 126.8(14) . . ?
C11 O2 C10 105.0(12) . . ?

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.029

####################################################################### 
# 
# 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_mm
_audit_block_doi                 10.5517/ccdc.csd.cc24dvn2
_database_code_depnum_ccdc_archive 'CCDC 1978564'
loop_
_audit_author_name
_audit_author_address
'Hongwei Wang'
;Northeast Normal University
China
;
_audit_update_record             
;
2020-01-20 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H14 Cl N O'
_chemical_formula_sum            'C19 H14 Cl N O'
_chemical_formula_weight         307.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.814(5)
_cell_length_b                   11.755(5)
_cell_length_c                   15.281(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 106.222(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1520.2(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2610
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_correction_T_min  0.810970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0564 before and 0.0262 after correction.
The Ratio of minimum to maximum transmission is 0.8110.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8503
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_min         2.220
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2432
_reflns_number_total             3106
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0592P)²+0.2215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1091
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
C1 C 0.4243(2) 0.19279(15) 0.96507(11) 0.0380(4) Uani 1 1 d . . . . .
C2 C 0.5645(2) 0.13419(19) 0.97936(12) 0.0496(5) Uani 1 1 d . . . . .
C3 C 0.6194(2) 0.10816(17) 0.90517(12) 0.0447(4) Uani 1 1 d . . . . .
C4 C 0.53613(17) 0.13944(13) 0.81761(10) 0.0314(4) Uani 1 1 d . . . . .
C5 C 0.3975(2) 0.20115(14) 0.80613(12) 0.0366(4) Uani 1 1 d . . . . .
C6 C 0.3408(2) 0.22782(15) 0.87944(12) 0.0380(4) Uani 1 1 d . . . . .
C7 C 0.59451(18) 0.10891(15) 0.73729(11) 0.0341(4) Uani 1 1 d . . . . .
C8 C 0.6743(2) -0.00030(16) 0.73248(12) 0.0390(4) Uani 1 1 d . . . . .
C9 C 0.50915(18) 0.01745(14) 0.66934(11) 0.0341(4) Uani 1 1 d . . . . .
C10 C 0.37849(18) -0.04337(13) 0.68823(11) 0.0306(3) Uani 1 1 d . . . . .
C11 C 0.24664(18) -0.07977(13) 0.62690(10) 0.0315(4) Uani 1 1 d . . . . .
C12 C 0.2229(2) -0.06031(16) 0.53091(12) 0.0454(5) Uani 1 1 d . . . . .
C13 C 0.12464(17) -0.15144(13) 0.65182(10) 0.0307(3) Uani 1 1 d . . . . .
C14 C 0.09685(16) -0.13460(13) 0.74308(10) 0.0272(3) Uani 1 1 d . . . . .
C15 C 0.10475(18) -0.02812(13) 0.78335(11) 0.0297(3) Uani 1 1 d . . . . .
C16 C 0.06586(19) -0.01457(15) 0.86492(11) 0.0349(4) Uani 1 1 d . . . . .
C17 C 0.02167(18) -0.10791(16) 0.90639(11) 0.0369(4) Uani 1 1 d . . . . .
C18 C 0.0153(2) -0.21478(15) 0.86764(12) 0.0367(4) Uani 1 1 d . . . . .
C19 C 0.05155(19) -0.22800(14) 0.78600(12) 0.0333(4) Uani 1 1 d . . . . .
N1 N 0.2009(3) -0.04225(19) 0.45489(11) 0.0763(6) Uani 1 1 d . . . . .
O1 O 0.05035(15) -0.22155(10) 0.59827(8) 0.0450(3) Uani 1 1 d . . . . .
Cl1 Cl 0.34901(6) 0.21976(5) 1.05720(3) 0.05685(19) Uani 1 1 d . . . . .
H2 H 0.621(2) 0.1126(18) 1.0391(15) 0.060(6) Uiso 1 1 d . . . . .
H3 H 0.715(3) 0.0682(18) 0.9130(14) 0.060(6) Uiso 1 1 d . . . . .
H5 H 0.334(2) 0.2238(16) 0.7441(15) 0.049(5) Uiso 1 1 d . . . . .
H6 H 0.248(2) 0.2676(16) 0.8706(13) 0.046(5) Uiso 1 1 d . . . . .
H7 H 0.626(2) 0.1724(17) 0.7084(12) 0.042(5) Uiso 1 1 d . . . . .
H8A H 0.6828(19) -0.0546(14) 0.7803(11) 0.030(4) Uiso 1 1 d . . . . .
H8B H 0.756(2) -0.0068(16) 0.7019(14) 0.055(6) Uiso 1 1 d . . . . .
H9 H 0.5011(19) 0.0313(14) 0.6076(12) 0.035(4) Uiso 1 1 d . . . . .
H10 H 0.3870(17) -0.0606(12) 0.7517(11) 0.022(4) Uiso 1 1 d . . . . .
H15 H 0.135(2) 0.0346(15) 0.7555(12) 0.035(4) Uiso 1 1 d . . . . .
H16 H 0.069(2) 0.0589(16) 0.8903(12) 0.039(5) Uiso 1 1 d . . . . .
H17 H -0.004(2) -0.0991(15) 0.9614(13) 0.045(5) Uiso 1 1 d . . . . .
H18 H -0.008(2) -0.2786(16) 0.8969(13) 0.043(5) Uiso 1 1 d . . . . .
H19 H 0.050(2) -0.3005(16) 0.7608(12) 0.038(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.378(3) . ?
C1 C6 1.373(3) . ?
C1 Cl1 1.7452(18) . ?
C2 C3 1.385(3) . ?
C2 H2 0.94(2) . ?
C3 C4 1.384(2) . ?
C3 H3 0.94(2) . ?
C4 C5 1.390(2) . ?
C4 C7 1.501(2) . ?
C5 C6 1.384(2) . ?
C5 H5 0.99(2) . ?
C6 H6 0.92(2) . ?
C7 C8 1.475(3) . ?
C7 C9 1.537(2) . ?
C7 H7 0.947(19) . ?
C8 C9 1.519(2) . ?
C8 H8A 0.957(17) . ?
C8 H8B 0.97(2) . ?
C9 C10 1.451(2) . ?
C9 H9 0.940(18) . ?
C10 C11 1.343(2) . ?
C10 H10 0.972(15) . ?
C11 C12 1.441(2) . ?
C11 C13 1.497(2) . ?
C12 N1 1.143(2) . ?
C13 C14 1.495(2) . ?
C13 O1 1.2159(18) . ?
C14 C15 1.388(2) . ?
C14 C19 1.393(2) . ?
C15 C16 1.391(2) . ?
C15 H15 0.925(18) . ?
C16 C17 1.377(2) . ?
C16 H16 0.944(18) . ?
C17 C18 1.383(3) . ?
C17 H17 0.936(19) . ?
C18 C19 1.380(2) . ?
C18 H18 0.927(19) . ?
C19 H19 0.934(18) . ?

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
C2 C1 Cl1 119.30(14) . . ?
C6 C1 C2 121.30(17) . . ?
C6 C1 Cl1 119.38(14) . . ?
C1 C2 C3 118.90(17) . . ?
C1 C2 H2 119.8(12) . . ?
C3 C2 H2 121.3(12) . . ?
C2 C3 H3 120.7(13) . . ?
C4 C3 C2 121.38(18) . . ?
C4 C3 H3 117.9(13) . . ?
C3 C4 C5 118.08(16) . . ?
C3 C4 C7 121.13(15) . . ?
C5 C4 C7 120.79(14) . . ?
C4 C5 H5 120.1(11) . . ?
C6 C5 C4 121.31(16) . . ?
C6 C5 H5 118.5(11) . . ?
C1 C6 C5 118.99(17) . . ?
C1 C6 H6 120.8(12) . . ?
C5 C6 H6 120.3(12) . . ?
C4 C7 C9 120.30(13) . . ?
C4 C7 H7 113.8(11) . . ?
C8 C7 C4 121.71(15) . . ?
C8 C7 C9 60.52(11) . . ?
C8 C7 H7 117.2(11) . . ?
C9 C7 H7 112.9(11) . . ?
C7 C8 C9 61.76(11) . . ?
C7 C8 H8A 118.7(10) . . ?
C7 C8 H8B 121.6(12) . . ?
C9 C8 H8A 115.7(10) . . ?
C9 C8 H8B 114.6(12) . . ?
H8A C8 H8B 113.9(15) . . ?
C7 C9 H9 116.2(10) . . ?
C8 C9 C7 57.72(11) . . ?
C8 C9 H9 116.9(10) . . ?
C10 C9 C7 118.42(14) . . ?
C10 C9 C8 118.59(15) . . ?
C10 C9 H9 116.3(10) . . ?
C9 C10 H10 117.2(9) . . ?
C11 C10 C9 126.75(15) . . ?
C11 C10 H10 116.1(9) . . ?
C10 C11 C12 120.74(15) . . ?
C10 C11 C13 123.03(14) . . ?
C12 C11 C13 115.98(13) . . ?
N1 C12 C11 177.9(2) . . ?
C14 C13 C11 118.65(13) . . ?
O1 C13 C11 120.03(14) . . ?
O1 C13 C14 121.32(14) . . ?
C15 C14 C13 122.14(14) . . ?
C15 C14 C19 119.17(15) . . ?
C19 C14 C13 118.55(14) . . ?
C14 C15 C16 120.41(15) . . ?
C14 C15 H15 120.0(10) . . ?
C16 C15 H15 119.6(11) . . ?
C15 C16 H16 119.2(11) . . ?
C17 C16 C15 119.56(16) . . ?
C17 C16 H16 121.3(11) . . ?
C16 C17 C18 120.64(15) . . ?
C16 C17 H17 119.7(12) . . ?
C18 C17 H17 119.6(11) . . ?
C17 C18 H18 121.1(11) . . ?
C19 C18 C17 119.82(16) . . ?
C19 C18 H18 119.1(11) . . ?
C14 C19 H19 119.7(11) . . ?
C18 C19 C14 120.39(16) . . ?
C18 C19 H19 119.8(11) . . ?

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 C2 C3 C4 -0.2(3) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C2 C3 C4 C7 -178.74(17) . . . . ?
C3 C4 C5 C6 -2.0(2) . . . . ?
C3 C4 C7 C8 36.4(2) . . . . ?
C3 C4 C7 C9 108.42(19) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C7 C8 C9 109.39(16) . . . . ?
C4 C7 C9 C8 -111.66(18) . . . . ?
C4 C7 C9 C10 -4.1(2) . . . . ?
C5 C4 C7 C8 -144.29(16) . . . . ?
C5 C4 C7 C9 -72.3(2) . . . . ?
C6 C1 C2 C3 -1.5(3) . . . . ?
C7 C4 C5 C6 178.68(15) . . . . ?
C7 C8 C9 C10 -107.27(17) . . . . ?
C7 C9 C10 C11 144.57(17) . . . . ?
C8 C7 C9 C10 107.56(18) . . . . ?
C8 C9 C10 C11 -148.80(17) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C9 C10 C11 C13 174.10(15) . . . . ?
C10 C11 C13 C14 32.7(2) . . . . ?
C10 C11 C13 O1 -147.36(16) . . . . ?
C11 C13 C14 C15 36.1(2) . . . . ?
C11 C13 C14 C19 -148.17(14) . . . . ?
C12 C11 C13 C14 -153.10(15) . . . . ?
C12 C11 C13 O1 26.8(2) . . . . ?
C13 C14 C15 C16 174.86(14) . . . . ?
C13 C14 C19 C18 -176.02(14) . . . . ?
C14 C15 C16 C17 1.0(2) . . . . ?
C15 C14 C19 C18 -0.1(2) . . . . ?
C15 C16 C17 C18 -0.1(2) . . . . ?
C16 C17 C18 C19 -0.9(2) . . . . ?
C17 C18 C19 C14 1.0(2) . . . . ?
C19 C14 C15 C16 -0.9(2) . . . . ?
O1 C13 C14 C15 -143.85(16) . . . . ?
O1 C13 C14 C19 31.9(2) . . . . ?
Cl1 C1 C2 C3 176.79(15) . . . . ?
Cl1 C1 C6 C5 -176.84(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
