# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_yy076
_database_code_depnum_ccdc_archive 'CCDC 2143525'
loop_
_audit_author_name
_audit_author_address
'Youngmee Kim'
;Ewha Womans University
South Korea
;
_audit_update_record             
;
2022-01-21 deposited with the CCDC.	2022-05-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            YV479
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 Cl2 N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         387.22

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4478(5)
_cell_length_b                   9.0425(6)
_cell_length_c                   12.7861(8)
_cell_angle_alpha                74.939(2)
_cell_angle_beta                 86.769(2)
_cell_angle_gamma                84.018(2)
_cell_volume                     826.61(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5827
_cell_measurement_theta_min      2.3426
_cell_measurement_theta_max      23.3716
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'light pink'
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396

_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             1.50
_diffrn_source_current           30.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            34242
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             4076
_reflns_number_gt                2116
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1801
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_number_reflns         4076
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0721P)²+0.4348P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.398
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.011(3)

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'

_computing_data_collection       'Bruker Instrument Service v2021.1.0.1'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1334(4) 0.7752(4) -0.0937(2) 0.0534(7) Uani d . . . 1 . .
C C2 0.1878(4) 0.7258(4) 0.0109(2) 0.0540(7) Uani d . . . 1 . .
H H2 0.183016 0.794201 0.054411 0.065 Uiso calc U . R 1 . .
C C3 0.2508(4) 0.5713(3) 0.0521(2) 0.0496(7) Uani d . . . 1 . .
C C4 0.2584(4) 0.4689(3) -0.0135(2) 0.0490(7) Uani d . . . 1 . .
C C5 0.2017(4) 0.5234(4) -0.1203(2) 0.0565(8) Uani d . . . 1 . .
H H5 0.206133 0.45633 -0.164754 0.068 Uiso calc U . R 1 . .
C C6 0.1396(4) 0.6748(4) -0.1599(2) 0.0575(8) Uani d . . . 1 . .
H H6 0.101804 0.710244 -0.230926 0.069 Uiso calc U . R 1 . .
C C7 0.3415(5) 0.2071(4) -0.0379(3) 0.0736(10) Uani d . . . 1 . .
H H7A 0.381433 0.106642 0.005448 0.11 Uiso calc U . R 1 . .
H H7B 0.428334 0.238912 -0.095708 0.11 Uiso calc U . R 1 . .
H H7C 0.226875 0.204189 -0.067637 0.11 Uiso calc U . R 1 . .
C C8 0.3769(4) 0.2650(4) 0.1351(3) 0.0565(8) Uani d . . . 1 . .
C C9 0.3525(4) 0.3814(4) 0.1982(2) 0.0550(8) Uani d . . . 1 . .
C C10 0.3963(4) 0.3268(4) 0.3157(2) 0.0549(8) Uani d . . . 1 . .
C C11 0.2742(4) 0.2192(4) 0.3840(2) 0.0569(8) Uani d . . . 1 . .
C C12 0.2120(5) 0.0479(4) 0.5596(3) 0.0672(9) Uani d . . . 1 . .
H H12A 0.129125 0.096571 0.603411 0.101 Uiso calc U . R 1 . .
H H12B 0.289344 -0.031094 0.605528 0.101 Uiso calc U . R 1 . .
H H12C 0.145657 0.003092 0.515267 0.101 Uiso calc U . R 1 . .
C C13 0.5707(4) 0.3195(3) 0.4591(2) 0.0524(7) Uani d . . . 1 . .
C C14 0.7202(4) 0.3672(4) 0.4970(3) 0.0597(8) Uani d . . . 1 . .
H H14 0.788718 0.438369 0.450359 0.072 Uiso calc U . R 1 . .
C C15 0.7668(4) 0.3095(4) 0.6028(3) 0.0611(8) Uani d . . . 1 . .
C C16 0.6657(5) 0.2045(4) 0.6738(3) 0.0640(9) Uani d . . . 1 . .
H H16 0.698758 0.166502 0.745586 0.077 Uiso calc U . R 1 . .
C C17 0.5171(4) 0.1565(4) 0.6384(2) 0.0588(8) Uani d . . . 1 . .
H H17 0.449 0.086481 0.686373 0.071 Uiso calc U . R 1 . .
C C18 0.4673(4) 0.2126(3) 0.5302(2) 0.0493(7) Uani d . . . 1 . .
Cl Cl1 0.05593(14) 0.96676(10) -0.14668(7) 0.0757(3) Uani d . . . 1 . .
Cl Cl2 0.95708(14) 0.36447(13) 0.64933(8) 0.0842(4) Uani d . . . 1 . .
N N1 0.3011(3) 0.5250(3) 0.15981(19) 0.0552(6) Uani d . . . 1 . .
N N2 0.3232(3) 0.3165(3) 0.0297(2) 0.0536(6) Uani d . . . 1 . .
N N3 0.3219(3) 0.1628(3) 0.48996(19) 0.0525(6) Uani d . . . 1 . .
N N4 0.5318(4) 0.3756(3) 0.3499(2) 0.0586(7) Uani d . . . 1 . .
O O1 0.4432(4) 0.1335(3) 0.1733(2) 0.0770(7) Uani d . . . 1 . .
O O2 0.1402(3) 0.1838(3) 0.34860(19) 0.0765(7) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.367(4) ?
C1 C6 . 1.388(4) ?
C1 Cl1 . 1.738(3) ?
C2 C3 . 1.399(4) ?
C2 H2 . 0.93 ?
C3 N1 . 1.392(3) ?
C3 C4 . 1.397(4) ?
C4 N2 . 1.390(4) ?
C4 C5 . 1.399(4) ?
C5 C6 . 1.371(4) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 N2 . 1.464(4) ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C8 O1 . 1.224(4) ?
C8 N2 . 1.375(4) ?
C8 C9 . 1.475(5) ?
C9 N1 . 1.288(4) ?
C9 C10 . 1.497(4) ?
C10 N4 . 1.283(4) ?
C10 C11 . 1.480(4) ?
C11 O2 . 1.224(4) ?
C11 N3 . 1.371(4) ?
C12 N3 . 1.468(4) ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
C13 C14 . 1.389(4) ?
C13 N4 . 1.392(4) ?
C13 C18 . 1.405(4) ?
C14 C15 . 1.368(4) ?
C14 H14 . 0.93 ?
C15 C16 . 1.384(5) ?
C15 Cl2 . 1.734(3) ?
C16 C17 . 1.370(4) ?
C16 H16 . 0.93 ?
C17 C18 . 1.401(4) ?
C17 H17 . 0.93 ?
C18 N3 . 1.388(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.2(3) ?
C2 C1 Cl1 . . 120.1(3) ?
C6 C1 Cl1 . . 118.7(2) ?
C1 C2 C3 . . 119.4(3) ?
C1 C2 H2 . . 120.3 ?
C3 C2 H2 . . 120.3 ?
N1 C3 C4 . . 122.3(3) ?
N1 C3 C2 . . 117.5(3) ?
C4 C3 C2 . . 120.2(3) ?
N2 C4 C3 . . 118.7(3) ?
N2 C4 C5 . . 122.4(3) ?
C3 C4 C5 . . 118.9(3) ?
C6 C5 C4 . . 120.6(3) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C1 . . 119.8(3) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
N2 C7 H7A . . 109.5 ?
N2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
N2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O1 C8 N2 . . 122.6(3) ?
O1 C8 C9 . . 122.5(3) ?
N2 C8 C9 . . 114.9(3) ?
N1 C9 C8 . . 125.3(3) ?
N1 C9 C10 . . 118.2(3) ?
C8 C9 C10 . . 116.4(3) ?
N4 C10 C11 . . 125.1(3) ?
N4 C10 C9 . . 119.3(3) ?
C11 C10 C9 . . 115.6(3) ?
O2 C11 N3 . . 122.5(3) ?
O2 C11 C10 . . 122.4(3) ?
N3 C11 C10 . . 115.1(3) ?
N3 C12 H12A . . 109.5 ?
N3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 N4 . . 118.5(3) ?
C14 C13 C18 . . 119.6(3) ?
N4 C13 C18 . . 121.8(3) ?
C15 C14 C13 . . 120.1(3) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 120.9(3) ?
C14 C15 Cl2 . . 120.2(3) ?
C16 C15 Cl2 . . 118.9(3) ?
C17 C16 C15 . . 120.0(3) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C16 C17 C18 . . 120.3(3) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
N3 C18 C17 . . 122.1(3) ?
N3 C18 C13 . . 118.7(2) ?
C17 C18 C13 . . 119.1(3) ?
C9 N1 C3 . . 117.1(3) ?
C8 N2 C4 . . 121.5(3) ?
C8 N2 C7 . . 118.1(3) ?
C4 N2 C7 . . 120.4(3) ?
C11 N3 C18 . . 121.5(2) ?
C11 N3 C12 . . 117.2(3) ?
C18 N3 C12 . . 121.2(2) ?
C10 N4 C13 . . 117.6(3) ?

