# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 2054567'
loop_
_audit_author_name
_audit_author_address
'Jing-Xin Liu' 'Anhui University of Technology'
_audit_update_record             
;
2021-01-08 deposited with the CCDC.	2022-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H52 Cl8 N4 O2 Zn2'
_chemical_formula_weight         1179.32

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.3073(18)
_cell_length_b                   18.584(3)
_cell_length_c                   14.516(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.319(4)
_cell_angle_gamma                90.00
_cell_volume                     2681.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      25.46

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1208
_exptl_absorpt_coefficient_mu    1.336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7398
_exptl_absorpt_correction_T_max  0.7949
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD Area Detector'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            59379
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5272
_reflns_number_gt                3498
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0458P)²+2.1429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       constr
_refine_ls_number_reflns         5272
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.26325(4) 0.17087(2) 0.49731(3) 0.03432(14) Uani 1 1 d . . .
Cl2 Cl 0.43748(10) 0.14299(5) 0.43589(7) 0.0497(3) Uani 1 1 d . . .
Cl3 Cl 0.13384(12) 0.26176(6) 0.41995(7) 0.0635(3) Uani 1 1 d . . .
Cl4 Cl 0.34505(10) 0.20230(6) 0.65242(6) 0.0569(3) Uani 1 1 d . . .
Cl1 Cl 0.13358(11) 0.07030(5) 0.48742(8) 0.0583(3) Uani 1 1 d . . .
N2 N 0.6864(3) 0.10765(14) 0.64497(18) 0.0317(6) Uani 1 1 d . . .
N1 N 1.3413(3) 0.45990(17) 0.7360(2) 0.0454(8) Uani 1 1 d . . .
C26 C 1.1336(3) 0.36298(19) 0.7146(2) 0.0355(8) Uani 1 1 d . . .
C25 C 0.9849(3) 0.26180(18) 0.6413(2) 0.0371(8) Uani 1 1 d . . .
H25A H 1.0256 0.2603 0.5912 0.045 Uiso 1 1 calc R . .
C24 C 1.0264(3) 0.31100(18) 0.7086(2) 0.0369(8) Uani 1 1 d . . .
H24A H 0.9826 0.3124 0.7569 0.044 Uiso 1 1 calc R . .
C23 C 0.6975(4) 0.16662(19) 0.6999(3) 0.0423(9) Uani 1 1 d . . .
H23A H 0.6399 0.1727 0.7389 0.051 Uiso 1 1 calc R . .
C22 C 0.8795(3) 0.21004(18) 0.6414(2) 0.0319(8) Uani 1 1 d . . .
C21 C 0.8627(4) 0.14922(19) 0.5843(2) 0.0398(9) Uani 1 1 d . . .
H21A H 0.9172 0.1425 0.5432 0.048 Uiso 1 1 calc R . .
C20 C 0.7917(4) 0.21764(19) 0.6991(3) 0.0417(9) Uani 1 1 d . . .
H20A H 0.7976 0.2581 0.7376 0.050 Uiso 1 1 calc R . .
C19 C 1.4265(4) 0.5737(2) 0.6834(3) 0.0446(10) Uani 1 1 d . . .
C18 C 1.1939(3) 0.37567(18) 0.6408(2) 0.0378(8) Uani 1 1 d . . .
H18A H 1.1648 0.3511 0.5832 0.045 Uiso 1 1 calc R . .
C17 C 0.6946(4) -0.0377(2) 0.7728(3) 0.0473(10) Uani 1 1 d . . .
H17A H 0.7319 -0.0586 0.7275 0.057 Uiso 1 1 calc R . .
C16 C 0.5836(4) 0.05200(19) 0.6496(2) 0.0412(9) Uani 1 1 d . . .
H16A H 0.5858 0.0138 0.6046 0.049 Uiso 1 1 calc R . .
H16B H 0.4948 0.0735 0.6318 0.049 Uiso 1 1 calc R . .
C15 C 1.1807(4) 0.4019(2) 0.7979(3) 0.0514(10) Uani 1 1 d . . .
H15A H 1.1412 0.3956 0.8479 0.062 Uiso 1 1 calc R . .
C14 C 1.2960(4) 0.4243(2) 0.6537(3) 0.0469(10) Uani 1 1 d . . .
H14A H 1.3352 0.4330 0.6040 0.056 Uiso 1 1 calc R . .
C13 C 0.7676(4) 0.09916(19) 0.5875(2) 0.0390(9) Uani 1 1 d . . .
H13A H 0.7590 0.0584 0.5491 0.047 Uiso 1 1 calc R . .
C12 C 0.5550(4) 0.0510(2) 0.8159(3) 0.0516(10) Uani 1 1 d . . .
H12A H 0.4973 0.0901 0.7998 0.062 Uiso 1 1 calc R . .
C11 C 1.4583(4) 0.5093(2) 0.7486(3) 0.0629(12) Uani 1 1 d . . .
H11A H 1.5332 0.4832 0.7359 0.075 Uiso 1 1 calc R . .
H11B H 1.4855 0.5256 0.8144 0.075 Uiso 1 1 calc R . .
C10 C 0.6102(3) 0.02113(19) 0.7483(2) 0.0377(9) Uani 1 1 d . . .
C9 C 1.3223(5) 0.6187(3) 0.6854(4) 0.0680(13) Uani 1 1 d . . .
H9A H 1.2689 0.6085 0.7263 0.082 Uiso 1 1 calc R . .
C8 C 1.5065(4) 0.5895(2) 0.6243(3) 0.0617(12) Uani 1 1 d . . .
H8A H 1.5773 0.5591 0.6220 0.074 Uiso 1 1 calc R . .
C7 C 1.2844(4) 0.4494(2) 0.8077(3) 0.0567(11) Uani 1 1 d . . .
H7A H 1.3158 0.4746 0.8646 0.068 Uiso 1 1 calc R . .
C6 C 0.5845(5) 0.0234(3) 0.9072(3) 0.0700(14) Uani 1 1 d . . .
H6A H 0.5472 0.0440 0.9527 0.084 Uiso 1 1 calc R . .
C5 C 0.6691(5) -0.0347(3) 0.9305(3) 0.0742(15) Uani 1 1 d . . .
H5A H 0.6893 -0.0531 0.9922 0.089 Uiso 1 1 calc R . .
C4 C 1.2958(6) 0.6771(3) 0.6294(5) 0.0952(19) Uani 1 1 d . . .
H4A H 1.2231 0.7064 0.6307 0.114 Uiso 1 1 calc R . .
C3 C 0.7238(5) -0.0656(2) 0.8641(3) 0.0630(12) Uani 1 1 d . . .
H3A H 0.7804 -0.1052 0.8804 0.076 Uiso 1 1 calc R . .
C2 C 1.4819(6) 0.6509(3) 0.5676(4) 0.0862(17) Uani 1 1 d . . .
H2A H 1.5369 0.6627 0.5284 0.103 Uiso 1 1 calc R . .
C1 C 1.3751(7) 0.6938(3) 0.5708(4) 0.0917(19) Uani 1 1 d . . .
H1A H 1.3565 0.7346 0.5326 0.110 Uiso 1 1 calc R . .
O1W O 1.5498(3) 0.33847(17) 0.7242(2) 0.0876(11) Uani 1 1 d . . .
H1WA H 1.5842 0.3209 0.7793 0.105 Uiso 1 1 d R . .
H1WB H 1.4911 0.3089 0.6936 0.105 Uiso 1 1 d R . .


_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 Cl3 2.2587(11) . ?
Zn1 Cl4 2.2624(10) . ?
Zn1 Cl2 2.2659(10) . ?
Zn1 Cl1 2.2800(11) . ?
N2 C13 1.339(4) . ?
N2 C23 1.342(4) . ?
N2 C16 1.495(4) . ?
N1 C14 1.336(5) . ?
N1 C7 1.336(5) . ?
N1 C11 1.488(5) . ?
C26 C15 1.382(5) . ?
C26 C18 1.394(4) . ?
C26 C24 1.452(5) . ?
C25 C24 1.324(5) . ?
C25 C22 1.452(5) . ?
C23 C20 1.359(5) . ?
C22 C21 1.385(5) . ?
C22 C20 1.393(5) . ?
C21 C13 1.360(5) . ?
C19 C9 1.367(6) . ?
C19 C8 1.370(5) . ?
C19 C11 1.508(5) . ?
C18 C14 1.361(5) . ?
C17 C3 1.380(5) . ?
C17 C10 1.384(5) . ?
C16 C10 1.499(5) . ?
C15 C7 1.364(5) . ?
C12 C10 1.374(5) . ?
C12 C6 1.378(5) . ?
C9 C4 1.340(7) . ?
C8 C2 1.390(7) . ?
C6 C5 1.372(7) . ?
C5 C3 1.366(6) . ?
C4 C1 1.362(8) . ?
C2 C1 1.369(8) . ?

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
Cl3 Zn1 Cl4 108.51(4) . . ?
Cl3 Zn1 Cl2 113.62(4) . . ?
Cl4 Zn1 Cl2 108.96(4) . . ?
Cl3 Zn1 Cl1 108.81(5) . . ?
Cl4 Zn1 Cl1 109.42(4) . . ?
Cl2 Zn1 Cl1 107.47(4) . . ?
C13 N2 C23 119.8(3) . . ?
C13 N2 C16 120.9(3) . . ?
C23 N2 C16 119.2(3) . . ?
C14 N1 C7 120.1(3) . . ?
C14 N1 C11 119.8(3) . . ?
C7 N1 C11 120.1(3) . . ?
C15 C26 C18 117.3(3) . . ?
C15 C26 C24 119.1(3) . . ?
C18 C26 C24 123.6(3) . . ?
C24 C25 C22 123.6(3) . . ?
C25 C24 C26 126.6(3) . . ?
N2 C23 C20 120.9(3) . . ?
C21 C22 C20 116.3(3) . . ?
C21 C22 C25 121.0(3) . . ?
C20 C22 C25 122.6(3) . . ?
C13 C21 C22 121.0(3) . . ?
C23 C20 C22 120.9(3) . . ?
C9 C19 C8 119.3(4) . . ?
C9 C19 C11 120.9(4) . . ?
C8 C19 C11 119.8(4) . . ?
C14 C18 C26 119.5(3) . . ?
C3 C17 C10 120.4(4) . . ?
N2 C16 C10 110.8(3) . . ?
C7 C15 C26 121.0(3) . . ?
N1 C14 C18 121.8(3) . . ?
N2 C13 C21 121.0(3) . . ?
C10 C12 C6 120.6(4) . . ?
N1 C11 C19 112.2(3) . . ?
C12 C10 C17 119.0(3) . . ?
C12 C10 C16 121.5(3) . . ?
C17 C10 C16 119.5(3) . . ?
C4 C9 C19 121.2(5) . . ?
C19 C8 C2 120.0(5) . . ?
N1 C7 C15 120.4(4) . . ?
C5 C6 C12 119.6(4) . . ?
C3 C5 C6 120.7(4) . . ?
C9 C4 C1 120.1(6) . . ?
C5 C3 C17 119.6(4) . . ?
C1 C2 C8 118.7(5) . . ?
C4 C1 C2 120.7(5) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.068
