# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2266553'
loop_
_audit_author_name
_audit_author_address
'Hui Jin'
;Shenyang University of Chemical Technology
China
;
_audit_update_record             
;
2023-05-31 deposited with the CCDC.	2023-07-17 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            'C12 H8 Cl N3 O'
_chemical_formula_weight         245.66

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.1261(7)
_cell_length_b                   7.8636(5)
_cell_length_c                   25.4825(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2229.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2047
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      19.42

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.327
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15315
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_av_R_equivalents  0.1092
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.198
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_full        25.003
_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             1957
_reflns_number_gt                1166
_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+0.9908P] 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         1957
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.1237(2) 0.5423(3) 0.62735(8) 0.0486(10) Uani 1 1 d G . . . .
H1 H 0.1225 0.5047 0.5928 0.058 Uiso 1 1 calc R U . . .
C2 C 0.01950(17) 0.5368(3) 0.65738(12) 0.0652(12) Uani 1 1 d G . . . .
H2 H -0.0514 0.4956 0.6429 0.078 Uiso 1 1 calc R U . . .
C3 C 0.0213(2) 0.5931(4) 0.70909(11) 0.0785(14) Uani 1 1 d G . . . .
H3 H -0.0484 0.5894 0.7292 0.094 Uiso 1 1 calc R U . . .
C4 C 0.1273(3) 0.6548(3) 0.73077(7) 0.0716(13) Uani 1 1 d G . . . .
H4 H 0.1285 0.6924 0.7654 0.086 Uiso 1 1 calc R U . . .
C5 C 0.2315(2) 0.6602(3) 0.70074(8) 0.0529(10) Uani 1 1 d G . . . .
H5 H 0.3025 0.7015 0.7152 0.063 Uiso 1 1 calc R U . . .
C6 C 0.22975(17) 0.6040(3) 0.64903(8) 0.0389(8) Uani 1 1 d G . . . .
C7 C 0.4368(3) 0.5209(4) 0.64056(14) 0.0408(9) Uani 1 1 d . . . . .
H7 H 0.4287 0.4631 0.6722 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5455(3) 0.5239(4) 0.61679(13) 0.0395(9) Uani 1 1 d . . . . .
C9 C 0.5597(3) 0.6097(4) 0.56728(13) 0.0393(9) Uani 1 1 d . . . . .
C10 C 0.4582(3) 0.6819(4) 0.54589(13) 0.0391(8) Uani 1 1 d . . . . .
C11 C 0.3438(3) 0.6809(4) 0.57033(13) 0.0392(8) Uani 1 1 d . . . . .
C12 C 0.6452(3) 0.4347(5) 0.63963(15) 0.0516(10) Uani 1 1 d . . . . .
Cl1 Cl 0.46768(8) 0.78360(12) 0.48631(3) 0.0525(3) Uani 1 1 d . . . . .
N1 N 0.3391(2) 0.5992(3) 0.61977(10) 0.0380(7) Uani 1 1 d . . . . .
N2 N 0.7261(3) 0.3655(5) 0.65653(14) 0.0747(11) Uani 1 1 d . . . . .
N3 N 0.6687(2) 0.6150(4) 0.54437(11) 0.0539(9) Uani 1 1 d . . . . .
H3A H 0.6777 0.6656 0.5147 0.065 Uiso 1 1 calc R U . . .
H3B H 0.7293 0.5678 0.5594 0.065 Uiso 1 1 calc R U . . .
O1 O 0.2520(2) 0.7498(3) 0.55324(9) 0.0511(7) 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 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 H1 0.9300 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 N1 1.428(3) . ?
C7 C8 1.353(4) . ?
C7 N1 1.357(4) . ?
C7 H7 0.9300 . ?
C8 C12 1.435(5) . ?
C8 C9 1.439(5) . ?
C9 N3 1.346(4) . ?
C9 C10 1.376(4) . ?
C10 C11 1.418(5) . ?
C10 Cl1 1.719(3) . ?
C11 O1 1.236(4) . ?
C11 N1 1.415(4) . ?
C12 N2 1.137(4) . ?
N3 H3A 0.8600 . ?
N3 H3B 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
C2 C1 C6 120.0 . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 N1 119.43(19) . . ?
C1 C6 N1 120.43(19) . . ?
C8 C7 N1 122.2(3) . . ?
C8 C7 H7 118.9 . . ?
N1 C7 H7 118.9 . . ?
C7 C8 C12 120.0(3) . . ?
C7 C8 C9 119.9(3) . . ?
C12 C8 C9 120.0(3) . . ?
N3 C9 C10 123.7(3) . . ?
N3 C9 C8 119.5(3) . . ?
C10 C9 C8 116.8(3) . . ?
C9 C10 C11 124.1(3) . . ?
C9 C10 Cl1 119.4(3) . . ?
C11 C10 Cl1 116.5(3) . . ?
O1 C11 N1 118.9(3) . . ?
O1 C11 C10 125.8(3) . . ?
N1 C11 C10 115.3(3) . . ?
N2 C12 C8 178.0(4) . . ?
C7 N1 C11 121.6(3) . . ?
C7 N1 C6 119.4(3) . . ?
C11 N1 C6 119.0(3) . . ?
C9 N3 H3A 120.0 . . ?
C9 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?

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 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 N1 -175.7(2) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C6 N1 175.6(2) . . . . ?
N1 C7 C8 C12 -178.2(3) . . . . ?
N1 C7 C8 C9 -1.2(5) . . . . ?
C7 C8 C9 N3 178.7(3) . . . . ?
C12 C8 C9 N3 -4.3(5) . . . . ?
C7 C8 C9 C10 -1.6(5) . . . . ?
C12 C8 C9 C10 175.4(3) . . . . ?
N3 C9 C10 C11 -178.3(3) . . . . ?
C8 C9 C10 C11 2.0(5) . . . . ?
N3 C9 C10 Cl1 0.7(5) . . . . ?
C8 C9 C10 Cl1 -178.9(3) . . . . ?
C9 C10 C11 O1 177.1(3) . . . . ?
Cl1 C10 C11 O1 -1.9(5) . . . . ?
C9 C10 C11 N1 0.2(5) . . . . ?
Cl1 C10 C11 N1 -178.8(2) . . . . ?
C8 C7 N1 C11 3.6(5) . . . . ?
C8 C7 N1 C6 -174.5(3) . . . . ?
O1 C11 N1 C7 179.8(3) . . . . ?
C10 C11 N1 C7 -3.1(4) . . . . ?
O1 C11 N1 C6 -2.1(4) . . . . ?
C10 C11 N1 C6 175.1(3) . . . . ?
C5 C6 N1 C7 50.9(3) . . . . ?
C1 C6 N1 C7 -124.7(3) . . . . ?
C5 C6 N1 C11 -127.2(2) . . . . ?
C1 C6 N1 C11 57.1(3) . . . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.058

