# 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_202010226
_database_code_depnum_ccdc_archive 'CCDC 2202803'
loop_
_audit_author_name
_audit_author_address
'wenbo cai'
;zhengzhou university
China
;
_audit_update_record             
;
2022-08-20 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Cl2 N3 O'
_chemical_formula_weight         359.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.4903(6)
_cell_length_b                   9.7844(8)
_cell_length_c                   10.1573(9)
_cell_angle_alpha                117.682(9)
_cell_angle_beta                 100.666(7)
_cell_angle_gamma                93.883(6)
_cell_volume                     807.88(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             370
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.696
_shelx_estimated_absorpt_T_min   0.589
_shelx_estimated_absorpt_T_max   0.709
_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      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5805
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.817
_diffrn_reflns_theta_max         67.084
_diffrn_reflns_theta_full        67.084
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2881
_reflns_number_gt                2291
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0538P)²+0.2293P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0036(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2881
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.5757(3) 0.8266(3) -0.1549(3) 0.0405(6) Uani 1 1 d . . . . .
C2 C 0.6130(3) 0.8611(3) 0.0003(3) 0.0382(6) Uani 1 1 d . . . . .
C3 C 0.7392(3) 0.9455(3) 0.1237(3) 0.0389(6) Uani 1 1 d . . . . .
C4 C 0.8595(3) 1.0246(3) 0.1091(3) 0.0474(7) Uani 1 1 d . . . . .
H4 H 0.8595 1.0208 0.0158 0.057 Uiso 1 1 calc R U . . .
C5 C 0.9769(3) 1.1074(3) 0.2320(4) 0.0538(8) Uani 1 1 d . . . . .
H5 H 1.0566 1.1585 0.2213 0.065 Uiso 1 1 calc R U . . .
C6 C 0.9777(3) 1.1156(3) 0.3716(4) 0.0529(8) Uani 1 1 d . . . . .
H6 H 1.0570 1.1743 0.4549 0.064 Uiso 1 1 calc R U . . .
C7 C 0.8620(3) 1.0375(3) 0.3885(3) 0.0476(7) Uani 1 1 d . . . . .
H7 H 0.8641 1.0428 0.4827 0.057 Uiso 1 1 calc R U . . .
C8 C 0.7410(3) 0.9501(3) 0.2647(3) 0.0394(6) Uani 1 1 d . . . . .
C9 C 0.6147(3) 0.8672(3) 0.2750(3) 0.0398(6) Uani 1 1 d . . . . .
C10 C 0.4935(3) 0.7921(3) 0.1599(3) 0.0376(6) Uani 1 1 d . . . . .
C11 C 0.3578(3) 0.7126(3) 0.1664(3) 0.0386(6) Uani 1 1 d . . . . .
C12 C 0.3514(3) 0.5679(3) 0.1589(4) 0.0534(7) Uani 1 1 d . . . . .
H12 H 0.4315 0.5176 0.1457 0.064 Uiso 1 1 calc R U . . .
C13 C 0.2272(3) 0.4970(3) 0.1707(4) 0.0582(8) Uani 1 1 d . . . . .
H13 H 0.2227 0.3989 0.1645 0.070 Uiso 1 1 calc R U . . .
C14 C 0.1110(3) 0.5729(3) 0.1917(3) 0.0509(7) Uani 1 1 d . . . . .
C15 C 0.1144(3) 0.7166(3) 0.1987(3) 0.0514(7) Uani 1 1 d . . . . .
H15 H 0.0340 0.7663 0.2118 0.062 Uiso 1 1 calc R U . . .
C16 C 0.2392(3) 0.7868(3) 0.1861(3) 0.0458(6) Uani 1 1 d . . . . .
H16 H 0.2429 0.8843 0.1910 0.055 Uiso 1 1 calc R U . . .
C17 C 0.3423(3) 0.6716(3) -0.3614(3) 0.0501(7) Uani 1 1 d . . . . .
H17A H 0.3876 0.7078 -0.4203 0.060 Uiso 1 1 calc R U . . .
H17B H 0.2499 0.7078 -0.3556 0.060 Uiso 1 1 calc R U . . .
C18 C 0.3150(4) 0.4949(4) -0.4431(4) 0.0671(9) Uani 1 1 d . . . . .
H18A H 0.2667 0.4582 -0.3874 0.101 Uiso 1 1 calc R U . . .
H18B H 0.4061 0.4583 -0.4495 0.101 Uiso 1 1 calc R U . . .
H18C H 0.2546 0.4556 -0.5446 0.101 Uiso 1 1 calc R U . . .
Cl1 Cl 0.61881(7) 0.86600(8) 0.44694(8) 0.0501(2) Uani 1 1 d . . . . .
Cl2 Cl -0.04519(10) 0.48625(11) 0.20980(11) 0.0791(3) Uani 1 1 d . . . . .
N1 N 0.4963(2) 0.7920(2) 0.0226(2) 0.0375(5) Uani 1 1 d . . . . .
N2 N 0.3873(2) 0.7171(3) -0.1016(2) 0.0427(5) Uani 1 1 d . . . . .
H2 H 0.3049 0.6660 -0.1120 0.051 Uiso 1 1 calc R U . . .
N3 N 0.4357(2) 0.7396(2) -0.2070(2) 0.0415(5) Uani 1 1 d . . . . .
O1 O 0.6424(2) 0.8600(2) -0.2334(2) 0.0549(5) Uani 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 O1 1.242(3) . ?
C1 N3 1.392(3) . ?
C1 C2 1.417(4) . ?
C2 N1 1.367(3) . ?
C2 C3 1.427(3) . ?
C3 C4 1.404(4) . ?
C3 C8 1.409(4) . ?
C4 C5 1.371(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.401(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.448(3) . ?
C9 C10 1.349(3) . ?
C9 Cl1 1.746(3) . ?
C10 N1 1.399(3) . ?
C10 C11 1.487(3) . ?
C11 C16 1.376(4) . ?
C11 C12 1.378(4) . ?
C12 C13 1.380(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(4) . ?
C14 Cl2 1.740(3) . ?
C15 C16 1.385(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N3 1.457(3) . ?
C17 C18 1.507(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 N2 1.324(3) . ?
N2 N3 1.339(3) . ?
N2 H2 0.8600 . ?

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
O1 C1 N3 125.4(2) . . ?
O1 C1 C2 132.6(2) . . ?
N3 C1 C2 102.1(2) . . ?
N1 C2 C1 106.4(2) . . ?
N1 C2 C3 119.9(2) . . ?
C1 C2 C3 133.8(2) . . ?
C4 C3 C8 119.6(2) . . ?
C4 C3 C2 122.2(2) . . ?
C8 C3 C2 118.2(2) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C3 118.8(2) . . ?
C7 C8 C9 123.4(2) . . ?
C3 C8 C9 117.8(2) . . ?
C10 C9 C8 123.9(2) . . ?
C10 C9 Cl1 118.0(2) . . ?
C8 C9 Cl1 118.12(19) . . ?
C9 C10 N1 116.2(2) . . ?
C9 C10 C11 126.3(2) . . ?
N1 C10 C11 117.5(2) . . ?
C16 C11 C12 119.6(2) . . ?
C16 C11 C10 119.7(2) . . ?
C12 C11 C10 120.7(2) . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.4(3) . . ?
C13 C14 Cl2 119.6(2) . . ?
C15 C14 Cl2 119.0(2) . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 120.2(3) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
N3 C17 C18 112.5(2) . . ?
N3 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
N3 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 N1 C2 113.4(2) . . ?
N2 N1 C10 122.6(2) . . ?
C2 N1 C10 124.0(2) . . ?
N1 N2 N3 103.66(19) . . ?
N1 N2 H2 128.2 . . ?
N3 N2 H2 128.2 . . ?
N2 N3 C1 114.5(2) . . ?
N2 N3 C17 119.0(2) . . ?
C1 N3 C17 126.5(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
O1 C1 C2 N1 -179.5(3) . . . . ?
N3 C1 C2 N1 0.6(3) . . . . ?
O1 C1 C2 C3 -0.2(5) . . . . ?
N3 C1 C2 C3 179.9(3) . . . . ?
N1 C2 C3 C4 -177.1(2) . . . . ?
C1 C2 C3 C4 3.7(5) . . . . ?
N1 C2 C3 C8 2.2(4) . . . . ?
C1 C2 C3 C8 -177.0(3) . . . . ?
C8 C3 C4 C5 -0.9(4) . . . . ?
C2 C3 C4 C5 178.4(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C7 1.6(5) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C6 C7 C8 C3 -0.9(4) . . . . ?
C6 C7 C8 C9 -179.0(3) . . . . ?
C4 C3 C8 C7 1.7(4) . . . . ?
C2 C3 C8 C7 -177.6(2) . . . . ?
C4 C3 C8 C9 179.9(2) . . . . ?
C2 C3 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C10 175.1(3) . . . . ?
C3 C8 C9 C10 -3.0(4) . . . . ?
C7 C8 C9 Cl1 -4.3(4) . . . . ?
C3 C8 C9 Cl1 177.61(19) . . . . ?
C8 C9 C10 N1 2.4(4) . . . . ?
Cl1 C9 C10 N1 -178.21(18) . . . . ?
C8 C9 C10 C11 -176.5(2) . . . . ?
Cl1 C9 C10 C11 2.9(4) . . . . ?
C9 C10 C11 C16 100.9(3) . . . . ?
N1 C10 C11 C16 -78.0(3) . . . . ?
C9 C10 C11 C12 -76.5(4) . . . . ?
N1 C10 C11 C12 104.6(3) . . . . ?
C16 C11 C12 C13 0.1(4) . . . . ?
C10 C11 C12 C13 177.5(3) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C12 C13 C14 C15 1.1(5) . . . . ?
C12 C13 C14 Cl2 -179.0(2) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
Cl2 C14 C15 C16 179.3(2) . . . . ?
C12 C11 C16 C15 0.2(4) . . . . ?
C10 C11 C16 C15 -177.3(2) . . . . ?
C14 C15 C16 C11 0.2(4) . . . . ?
C1 C2 N1 N2 -0.2(3) . . . . ?
C3 C2 N1 N2 -179.6(2) . . . . ?
C1 C2 N1 C10 176.5(2) . . . . ?
C3 C2 N1 C10 -2.9(4) . . . . ?
C9 C10 N1 N2 177.0(2) . . . . ?
C11 C10 N1 N2 -3.9(3) . . . . ?
C9 C10 N1 C2 0.6(4) . . . . ?
C11 C10 N1 C2 179.6(2) . . . . ?
C2 N1 N2 N3 -0.3(3) . . . . ?
C10 N1 N2 N3 -177.1(2) . . . . ?
N1 N2 N3 C1 0.8(3) . . . . ?
N1 N2 N3 C17 179.8(2) . . . . ?
O1 C1 N3 N2 179.2(3) . . . . ?
C2 C1 N3 N2 -0.9(3) . . . . ?
O1 C1 N3 C17 0.3(4) . . . . ?
C2 C1 N3 C17 -179.8(2) . . . . ?
C18 C17 N3 N2 -65.2(3) . . . . ?
C18 C17 N3 C1 113.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 Cl2 0.86 2.55 3.388(2) 165.1 2_565

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.046

