# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_i17819
_database_code_depnum_ccdc_archive 'CCDC 2173865'
loop_
_audit_author_name
_audit_author_address
'Yuh-Sheng Wen'
;Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-05-20 deposited with the CCDC.	2023-01-09 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         'C25 H18 Cl2 N3 Zn'
_chemical_formula_sum            'C25 H18 Cl2 N3 Zn'
_chemical_formula_weight         496.69

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           68
_space_group_name_H-M_alt        'C c c a'
_space_group_name_Hall           '-C 2b 2bc'

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

_cell_length_a                   13.8231(4)
_cell_length_b                   20.1276(6)
_cell_length_c                   16.7673(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4665.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    8852
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      27.04

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             2024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.121
_exptl_absorpt_coefficient_mu    1.299
_shelx_estimated_absorpt_T_min   0.806
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.9989
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(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            56938
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.161
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.242
_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             2584
_reflns_number_gt                2104
_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.

 Structure factors included contributions from the .fab file.

 _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 Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1088P)²+31.5496P] 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         2584
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1913
_refine_ls_wR_factor_gt          0.1762
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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
Zn1 Zn 0.500000 0.46852(3) 0.250000 0.0198(2) Uani 1 2 d S T P . .
Cl1 Cl 0.59946(7) 0.41476(5) 0.16924(6) 0.0253(3) Uani 1 1 d . . . . .
N1 N 1.000000 0.750000 0.5818(2) 0.0108(8) Uani 1 2 d S T P . .
N2 N 0.5863(2) 0.52631(17) 0.3195(2) 0.0192(7) Uani 1 1 d . . . . .
C1 C 0.9307(2) 0.71190(17) 0.5413(2) 0.0114(7) Uani 1 1 d . . . . .
C2 C 0.8381(3) 0.70198(19) 0.5732(2) 0.0152(7) Uani 1 1 d . . . . .
H2 H 0.822042 0.720870 0.623413 0.018 Uiso 1 1 calc R U . . .
C3 C 0.7698(3) 0.66489(19) 0.5323(2) 0.0155(7) Uani 1 1 d . . . . .
H3 H 0.707806 0.657945 0.555310 0.019 Uiso 1 1 calc R U . . .
C4 C 0.7907(3) 0.63755(18) 0.4576(2) 0.0146(7) Uani 1 1 d . . . . .
C5 C 0.8838(3) 0.64662(19) 0.4267(2) 0.0153(7) Uani 1 1 d . . . . .
H5 H 0.899677 0.627963 0.376382 0.018 Uiso 1 1 calc R U . . .
C6 C 0.9529(3) 0.68218(18) 0.4681(2) 0.0141(7) Uani 1 1 d . . . . .
H6 H 1.016202 0.686525 0.446602 0.017 Uiso 1 1 calc R U . . .
C7 C 0.7186(3) 0.60039(19) 0.4108(2) 0.0161(7) Uani 1 1 d . . . . .
C8 C 0.6411(3) 0.5672(2) 0.4461(2) 0.0192(8) Uani 1 1 d . . . . .
H8 H 0.631861 0.569550 0.502169 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5775(3) 0.5309(2) 0.3995(2) 0.0194(8) Uani 1 1 d . . . . .
H9 H 0.525542 0.508363 0.424833 0.023 Uiso 1 1 calc R U . . .
C10 C 0.6596(3) 0.5591(2) 0.2846(2) 0.0193(8) Uani 1 1 d . . . . .
H10 H 0.666400 0.556544 0.228308 0.023 Uiso 1 1 calc R U . . .
C11 C 0.7253(3) 0.5963(2) 0.3276(2) 0.0186(8) Uani 1 1 d . . . . .
H11 H 0.775479 0.619296 0.300452 0.022 Uiso 1 1 calc R U . . .
C12 C 1.000000 0.750000 0.6673(3) 0.0099(9) Uani 1 2 d S T P . .
C13 C 0.9996(3) 0.80971(18) 0.7085(2) 0.0139(7) Uani 1 1 d . . . . .
H13 H 0.998874 0.850553 0.680100 0.017 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
Zn1 N2 2.033(3) . ?
Zn1 N2 2.033(3) 3_655 ?
Zn1 Cl1 2.2123(10) 3_655 ?
Zn1 Cl1 2.2124(10) . ?
N1 C1 1.403(4) 6_665 ?
N1 C1 1.403(4) . ?
N1 C12 1.434(6) . ?
N2 C10 1.343(5) . ?
N2 C9 1.349(5) . ?
C1 C6 1.400(5) . ?
C1 C2 1.401(5) . ?
C2 C3 1.386(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(5) . ?
C4 C7 1.473(5) . ?
C5 C6 1.381(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.395(5) . ?
C7 C11 1.401(5) . ?
C8 C9 1.385(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.380(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.386(4) . ?
C12 C13 1.386(4) 6_665 ?
C13 C13 1.392(7) 3_756 ?
C13 H13 0.9500 . ?

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
N2 Zn1 N2 110.2(2) . 3_655 ?
N2 Zn1 Cl1 107.05(11) . 3_655 ?
N2 Zn1 Cl1 105.44(10) 3_655 3_655 ?
N2 Zn1 Cl1 105.44(10) . . ?
N2 Zn1 Cl1 107.05(11) 3_655 . ?
Cl1 Zn1 Cl1 121.44(6) 3_655 . ?
C1 N1 C1 122.1(4) 6_665 . ?
C1 N1 C12 118.9(2) 6_665 . ?
C1 N1 C12 118.9(2) . . ?
C10 N2 C9 117.9(3) . . ?
C10 N2 Zn1 118.2(3) . . ?
C9 N2 Zn1 123.8(3) . . ?
C6 C1 C2 118.3(3) . . ?
C6 C1 N1 120.5(3) . . ?
C2 C1 N1 121.1(3) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.1(3) . . ?
C3 C4 C7 122.5(3) . . ?
C5 C4 C7 119.4(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C8 C7 C11 116.4(3) . . ?
C8 C7 C4 122.5(3) . . ?
C11 C7 C4 121.1(3) . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
N2 C9 C8 122.7(4) . . ?
N2 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
N2 C10 C11 122.4(4) . . ?
N2 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C7 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C7 C11 H11 119.7 . . ?
C13 C12 C13 120.2(5) . 6_665 ?
C13 C12 N1 119.9(2) . . ?
C13 C12 N1 119.9(2) 6_665 . ?
C12 C13 C13 119.9(2) . 3_756 ?
C12 C13 H13 120.1 . . ?
C13 C13 H13 120.1 3_756 . ?

_refine_diff_density_max         0.791
_refine_diff_density_min         -1.267
_refine_diff_density_rms         0.173




