# Supplementary Information (SI) for RSC Mechanochemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_8s
_database_code_depnum_ccdc_archive 'CCDC 2411964'
loop_
_audit_author_name
_audit_author_address
'Paolo Pio Mazzeo'
;University of Parma
Italy
;
_audit_update_record             
;
2025-02-11 deposited with the CCDC.	2025-03-03 downloaded from the CCDC.
;
_audit_creation_date             2025-02-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 Br2 N2 O4 Zn'
_chemical_formula_sum            'C24 H18 Br2 N2 O4 Zn'
_chemical_formula_weight         623.59
_chemical_melting_point          ?
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'
Br Br -0.6763 1.2805 '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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.7920(9)
_cell_length_b                   6.1334(2)
_cell_length_c                   15.1547(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.997(2)
_cell_angle_gamma                90
_cell_volume                     2395.91(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6950
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      69.448
_cell_measurement_theta_min      4.582
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.613
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1070 before and 0.0715 after correction.
The Ratio of minimum to maximum transmission is 0.7608.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18782
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.168
_diffrn_reflns_theta_min         3.429
_diffrn_ambient_temperature      299.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon III'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1805
_reflns_number_total             2281
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+2.2457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0808
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C6(H6), C3(H3), C4(H4), C12(H12), C9(H9), C11(H11), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.40347(7) 0.750000 0.04907(15) Uani 1 2 d S T P . .
Br1 Br 0.78568(2) 1.08169(6) 0.62742(3) 0.07685(15) Uani 1 1 d . . . . .
O1 O 0.55428(7) 0.6101(3) 0.72016(15) 0.0608(5) Uani 1 1 d . . . . .
N1 N 0.46402(8) 0.2035(4) 0.65888(15) 0.0498(5) Uani 1 1 d . . . . .
O2 O 0.58680(9) 0.3427(4) 0.64293(18) 0.0802(7) Uani 1 1 d . . . . .
C2 C 0.63697(10) 0.6638(4) 0.66192(17) 0.0462(6) Uani 1 1 d . . . . .
C1 C 0.58893(10) 0.5266(4) 0.67412(19) 0.0517(6) Uani 1 1 d . . . . .
C7 C 0.64034(10) 0.8732(4) 0.69658(19) 0.0527(6) Uani 1 1 d . . . . .
H7 H 0.612669 0.930797 0.726694 0.063 Uiso 1 1 calc R U . . .
C8 C 0.48520(11) 0.0147(5) 0.6349(2) 0.0580(7) Uani 1 1 d . . . . .
H8 H 0.517553 -0.023992 0.658994 0.070 Uiso 1 1 calc R U . . .
C5 C 0.72522(10) 0.9099(4) 0.64220(19) 0.0528(6) Uani 1 1 d . . . . .
C6 C 0.68468(11) 0.9965(5) 0.6865(2) 0.0569(7) Uani 1 1 d . . . . .
H6 H 0.686922 1.136817 0.709611 0.068 Uiso 1 1 calc R U . . .
C3 C 0.67873(11) 0.5806(4) 0.61801(18) 0.0531(6) Uani 1 1 d . . . . .
H3 H 0.676765 0.440423 0.594787 0.064 Uiso 1 1 calc R U . . .
C4 C 0.72310(11) 0.7013(5) 0.60802(19) 0.0571(7) Uani 1 1 d . . . . .
H4 H 0.751098 0.643518 0.578835 0.069 Uiso 1 1 calc R U . . .
C12 C 0.41722(11) 0.2558(5) 0.6236(2) 0.0644(8) Uani 1 1 d . . . . .
H12 H 0.401628 0.385232 0.640485 0.077 Uiso 1 1 calc R U . . .
C9 C 0.46077(14) -0.1242(5) 0.5757(2) 0.0717(9) Uani 1 1 d . . . . .
H9 H 0.476293 -0.255278 0.560653 0.086 Uiso 1 1 calc R U . . .
C11 C 0.39182(14) 0.1244(7) 0.5634(2) 0.0827(11) Uani 1 1 d . . . . .
H11 H 0.359775 0.166303 0.539017 0.099 Uiso 1 1 calc R U . . .
C10 C 0.41356(16) -0.0682(7) 0.5393(2) 0.0817(10) Uani 1 1 d . . . . .
H10 H 0.396518 -0.159615 0.498872 0.098 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 O1 1.9532(19) . ?
Zn1 O1 1.9533(18) 2_656 ?
Zn1 N1 2.045(2) . ?
Zn1 N1 2.045(2) 2_656 ?
Br1 C5 1.902(3) . ?
O1 C1 1.261(3) . ?
N1 C8 1.337(4) . ?
N1 C12 1.342(3) . ?
O2 C1 1.223(3) . ?
C2 C1 1.515(4) . ?
C2 C7 1.389(4) . ?
C2 C3 1.383(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.384(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(4) . ?
C5 C6 1.370(4) . ?
C5 C4 1.381(4) . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.376(4) . ?
C4 H4 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.366(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(5) . ?
C11 H11 0.9300 . ?
C11 C10 1.363(5) . ?
C10 H10 0.9300 . ?

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 Zn1 O1 99.07(11) . 2_656 ?
O1 Zn1 N1 123.01(9) . . ?
O1 Zn1 N1 103.50(8) . 2_656 ?
O1 Zn1 N1 103.50(8) 2_656 . ?
O1 Zn1 N1 123.01(9) 2_656 2_656 ?
N1 Zn1 N1 106.31(12) 2_656 . ?
C1 O1 Zn1 113.07(17) . . ?
C8 N1 Zn1 121.56(18) . . ?
C8 N1 C12 118.0(3) . . ?
C12 N1 Zn1 120.4(2) . . ?
C7 C2 C1 120.5(2) . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 C7 118.9(3) . . ?
O1 C1 C2 116.1(2) . . ?
O2 C1 O1 124.4(3) . . ?
O2 C1 C2 119.4(2) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.3(3) . . ?
C6 C7 H7 119.9 . . ?
N1 C8 H8 118.9 . . ?
N1 C8 C9 122.2(3) . . ?
C9 C8 H8 118.9 . . ?
C6 C5 Br1 119.1(2) . . ?
C6 C5 C4 121.5(3) . . ?
C4 C5 Br1 119.4(2) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 C7 119.3(3) . . ?
C5 C6 H6 120.3 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.4 . . ?
C5 C4 H4 120.7 . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 H4 120.7 . . ?
N1 C12 H12 119.0 . . ?
N1 C12 C11 121.9(3) . . ?
C11 C12 H12 119.0 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C12 C11 H11 120.1 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.1 . . ?
C9 C10 H10 120.7 . . ?
C11 C10 C9 118.7(3) . . ?
C11 C10 H10 120.7 . . ?

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
Zn1 O1 C1 O2 7.3(4) . . . . ?
Zn1 O1 C1 C2 -169.56(17) . . . . ?
Zn1 N1 C8 C9 178.0(2) . . . . ?
Zn1 N1 C12 C11 -179.1(3) . . . . ?
Br1 C5 C6 C7 179.2(2) . . . . ?
Br1 C5 C4 C3 -178.9(2) . . . . ?
N1 C8 C9 C10 0.6(5) . . . . ?
N1 C12 C11 C10 1.5(6) . . . . ?
C2 C7 C6 C5 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C1 C2 C7 C6 178.9(3) . . . . ?
C1 C2 C3 C4 -178.6(3) . . . . ?
C7 C2 C1 O1 -3.1(4) . . . . ?
C7 C2 C1 O2 179.9(3) . . . . ?
C7 C2 C3 C4 -0.2(4) . . . . ?
C8 N1 C12 C11 -1.3(5) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C6 C5 C4 C3 1.0(4) . . . . ?
C3 C2 C1 O1 175.3(3) . . . . ?
C3 C2 C1 O2 -1.7(4) . . . . ?
C3 C2 C7 C6 0.5(4) . . . . ?
C4 C5 C6 C7 -0.6(4) . . . . ?
C12 N1 C8 C9 0.3(4) . . . . ?
C12 C11 C10 C9 -0.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2s
_database_code_depnum_ccdc_archive 'CCDC 2411967'
loop_
_audit_author_name
_audit_author_address
'Paolo Pio Mazzeo'
;University of Parma
Italy
;
_audit_update_record             
;
2024-12-20 deposited with the CCDC.	2025-03-03 downloaded from the CCDC.
;
_audit_creation_date             2024-11-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 Br2 N2 O5 Zn'
_chemical_formula_sum            'C24 H20 Br2 N2 O5 Zn'
_chemical_formula_weight         641.61
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   15.382(6)
_cell_length_b                   5.866(2)
_cell_length_c                   27.370(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.924(5)
_cell_angle_gamma                90
_cell_volume                     2424.9(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    296.00
_cell_measurement_theta_max      27.809
_cell_measurement_theta_min      2.854
_shelx_estimated_absorpt_T_max   0.780
_shelx_estimated_absorpt_T_min   0.410
_exptl_absorpt_coefficient_mu    4.347
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1146 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.6716.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            73004
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         2.697
_diffrn_ambient_temperature      296.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture Photon III'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5079
_reflns_number_total             5994
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.799
_refine_diff_density_min         -1.538
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         5994
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+2.9703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C3(H3), C7(H7), C19(H19), C6(H6), C15(H15), C4(H4), C14(H14),
 C10(H10), C20(H20), C23(H23), C13(H13), C11(H11), C22(H22), C21(H21), C17(H17),
  C16(H16), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.63648(2) 0.62686(5) 0.37591(2) 0.02946(9) Uani 1 1 d . . . . .
Br1 Br 0.06617(2) 0.56394(8) 0.28390(2) 0.07573(15) Uani 1 1 d . . . . .
Br2 Br 1.16765(3) 1.19632(11) 0.45273(2) 0.0967(2) Uani 1 1 d . . . . .
O3 O 0.61886(15) 0.2839(3) 0.36370(8) 0.0392(4) Uani 1 1 d . . . . .
O5 O 0.72538(12) 0.9288(3) 0.39977(7) 0.0426(4) Uani 1 1 d . . . . .
O4 O 0.78173(13) 0.5928(3) 0.39029(8) 0.0439(5) Uani 1 1 d . . . . .
O2 O 0.50749(12) 0.7022(4) 0.36079(8) 0.0462(5) Uani 1 1 d . . . . .
N1 N 0.63231(14) 0.5923(4) 0.45413(8) 0.0358(5) Uani 1 1 d . . . . .
N2 N 0.63564(14) 0.6958(4) 0.29755(8) 0.0351(4) Uani 1 1 d . . . . .
O1 O 0.46946(14) 1.0649(4) 0.36837(10) 0.0562(6) Uani 1 1 d . . . . .
C8 C 0.79147(16) 0.7995(5) 0.40117(9) 0.0349(5) Uani 1 1 d . . . . .
C2 C 0.35818(15) 0.7953(4) 0.33672(9) 0.0310(5) Uani 1 1 d . . . . .
C1 C 0.45292(16) 0.8635(5) 0.35656(9) 0.0345(5) Uani 1 1 d . . . . .
C9 C 0.88297(16) 0.8961(4) 0.41539(9) 0.0339(5) Uani 1 1 d . . . . .
C24 C 0.67053(19) 0.8814(5) 0.28061(10) 0.0414(6) Uani 1 1 d . . . . .
H24 H 0.697250 0.989302 0.303518 0.050 Uiso 1 1 calc R U . . .
C3 C 0.28940(17) 0.9393(5) 0.34251(10) 0.0385(6) Uani 1 1 d . . . . .
H3 H 0.301915 1.081318 0.357262 0.046 Uiso 1 1 calc R U . . .
C5 C 0.18504(17) 0.6636(5) 0.30448(11) 0.0418(6) Uani 1 1 d . . . . .
C7 C 0.33888(17) 0.5858(5) 0.31402(10) 0.0370(5) Uani 1 1 d . . . . .
H7 H 0.384817 0.489142 0.309826 0.044 Uiso 1 1 calc R U . . .
C19 C 0.6614(2) 0.4111(5) 0.48163(11) 0.0468(7) Uani 1 1 d . . . . .
H19 H 0.687929 0.293036 0.467175 0.056 Uiso 1 1 calc R U . . .
C6 C 0.25191(18) 0.5182(5) 0.29747(11) 0.0410(6) Uani 1 1 d . . . . .
H6 H 0.239023 0.377846 0.281975 0.049 Uiso 1 1 calc R U . . .
C15 C 0.5953(2) 0.7601(5) 0.47578(11) 0.0446(6) Uani 1 1 d . . . . .
H15 H 0.575388 0.888378 0.457011 0.053 Uiso 1 1 calc R U . . .
C4 C 0.20177(18) 0.8731(5) 0.32643(12) 0.0446(6) Uani 1 1 d . . . . .
H4 H 0.155521 0.969010 0.330485 0.054 Uiso 1 1 calc R U . . .
C14 C 0.8971(2) 1.1107(5) 0.43649(11) 0.0433(6) Uani 1 1 d . . . . .
H14 H 0.849386 1.196276 0.442611 0.052 Uiso 1 1 calc R U . . .
C10 C 0.95497(17) 0.7712(5) 0.40614(11) 0.0420(6) Uani 1 1 d . . . . .
H10 H 0.945920 0.626589 0.392196 0.050 Uiso 1 1 calc R U . . .
C20 C 0.5959(2) 0.5469(6) 0.26376(11) 0.0486(7) Uani 1 1 d . . . . .
H20 H 0.569563 0.418518 0.274651 0.058 Uiso 1 1 calc R U . . .
C23 C 0.6688(2) 0.9207(6) 0.23067(11) 0.0489(7) Uani 1 1 d . . . . .
H23 H 0.693837 1.052298 0.220351 0.059 Uiso 1 1 calc R U . . .
C13 C 0.9822(2) 1.1981(6) 0.44850(12) 0.0527(8) Uani 1 1 d . . . . .
H13 H 0.992101 1.340658 0.463364 0.063 Uiso 1 1 calc R U . . .
C12 C 1.0517(2) 1.0713(6) 0.43817(12) 0.0533(8) Uani 1 1 d . . . . .
C11 C 1.03992(19) 0.8591(6) 0.41740(12) 0.0535(8) Uani 1 1 d . . . . .
H11 H 1.087896 0.775603 0.410963 0.064 Uiso 1 1 calc R U . . .
C22 C 0.6298(2) 0.7635(6) 0.19668(11) 0.0509(7) Uani 1 1 d . . . . .
H22 H 0.628896 0.784160 0.162898 0.061 Uiso 1 1 calc R U . . .
C21 C 0.5920(3) 0.5749(6) 0.21347(12) 0.0578(8) Uani 1 1 d . . . . .
H21 H 0.564039 0.466589 0.191073 0.069 Uiso 1 1 calc R U . . .
C17 C 0.6140(2) 0.5649(7) 0.55256(11) 0.0564(8) Uani 1 1 d . . . . .
H17 H 0.606979 0.554187 0.585500 0.068 Uiso 1 1 calc R U . . .
C16 C 0.5852(2) 0.7524(6) 0.52486(11) 0.0530(8) Uani 1 1 d . . . . .
H16 H 0.559197 0.873356 0.538722 0.064 Uiso 1 1 calc R U . . .
C18 C 0.6535(3) 0.3920(6) 0.53097(12) 0.0576(8) Uani 1 1 d . . . . .
H18 H 0.674672 0.263432 0.549304 0.069 Uiso 1 1 calc R U . . .
H3A H 0.656(3) 0.200(7) 0.3759(15) 0.066(12) Uiso 1 1 d . . . . .
H3B H 0.580(3) 0.212(7) 0.3655(15) 0.067(13) Uiso 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
Zn1 O3 2.049(2) . ?
Zn1 O5 2.257(2) . ?
Zn1 O4 2.203(2) . ?
Zn1 O2 1.998(2) . ?
Zn1 N1 2.163(2) . ?
Zn1 N2 2.180(2) . ?
Zn1 C8 2.562(3) . ?
Br1 C5 1.901(3) . ?
Br2 C12 1.899(3) . ?
O3 H3A 0.78(4) . ?
O3 H3B 0.74(4) . ?
O5 C8 1.263(3) . ?
O4 C8 1.251(3) . ?
O2 C1 1.256(3) . ?
N1 C19 1.330(4) . ?
N1 C15 1.331(4) . ?
N2 C24 1.335(4) . ?
N2 C20 1.333(4) . ?
O1 C1 1.238(3) . ?
C8 C9 1.499(3) . ?
C2 C1 1.510(3) . ?
C2 C3 1.386(4) . ?
C2 C7 1.384(4) . ?
C9 C14 1.385(4) . ?
C9 C10 1.391(4) . ?
C24 H24 0.9300 . ?
C24 C23 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(4) . ?
C5 C6 1.378(4) . ?
C5 C4 1.371(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.386(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.383(4) . ?
C6 H6 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.382(4) . ?
C4 H4 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.386(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(4) . ?
C23 H23 0.9300 . ?
C23 C22 1.365(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.376(5) . ?
C12 C11 1.366(5) . ?
C11 H11 0.9300 . ?
C22 H22 0.9300 . ?
C22 C21 1.369(5) . ?
C21 H21 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.362(5) . ?
C17 C18 1.372(5) . ?
C16 H16 0.9300 . ?
C18 H18 0.9300 . ?

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
O3 Zn1 O5 150.67(8) . . ?
O3 Zn1 O4 92.20(8) . . ?
O3 Zn1 N1 92.38(9) . . ?
O3 Zn1 N2 92.61(9) . . ?
O3 Zn1 C8 121.32(9) . . ?
O5 Zn1 C8 29.53(8) . . ?
O4 Zn1 O5 58.75(7) . . ?
O4 Zn1 C8 29.22(8) . . ?
O2 Zn1 O3 95.04(9) . . ?
O2 Zn1 O5 114.20(9) . . ?
O2 Zn1 O4 172.21(8) . . ?
O2 Zn1 N1 90.64(8) . . ?
O2 Zn1 N2 86.26(8) . . ?
O2 Zn1 C8 143.64(9) . . ?
N1 Zn1 O5 85.25(8) . . ?
N1 Zn1 O4 91.95(8) . . ?
N1 Zn1 N2 174.33(8) . . ?
N1 Zn1 C8 88.32(8) . . ?
N2 Zn1 O5 91.69(8) . . ?
N2 Zn1 O4 90.53(8) . . ?
N2 Zn1 C8 91.37(8) . . ?
Zn1 O3 H3A 119(3) . . ?
Zn1 O3 H3B 129(3) . . ?
H3A O3 H3B 99(4) . . ?
C8 O5 Zn1 88.73(16) . . ?
C8 O4 Zn1 91.50(16) . . ?
C1 O2 Zn1 143.69(19) . . ?
C19 N1 Zn1 124.43(19) . . ?
C19 N1 C15 117.7(2) . . ?
C15 N1 Zn1 117.81(19) . . ?
C24 N2 Zn1 124.39(18) . . ?
C20 N2 Zn1 118.49(18) . . ?
C20 N2 C24 117.1(2) . . ?
O5 C8 Zn1 61.75(14) . . ?
O5 C8 C9 119.5(2) . . ?
O4 C8 Zn1 59.28(14) . . ?
O4 C8 O5 121.0(2) . . ?
O4 C8 C9 119.5(2) . . ?
C9 C8 Zn1 178.7(2) . . ?
C3 C2 C1 120.2(2) . . ?
C7 C2 C1 120.5(2) . . ?
C7 C2 C3 119.3(2) . . ?
O2 C1 C2 114.6(2) . . ?
O1 C1 O2 126.5(2) . . ?
O1 C1 C2 118.9(2) . . ?
C14 C9 C8 121.1(3) . . ?
C14 C9 C10 119.2(3) . . ?
C10 C9 C8 119.7(2) . . ?
N2 C24 H24 118.5 . . ?
N2 C24 C23 123.1(3) . . ?
C23 C24 H24 118.5 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C6 C5 Br1 118.0(2) . . ?
C4 C5 Br1 119.7(2) . . ?
C4 C5 C6 122.2(3) . . ?
C2 C7 H7 119.6 . . ?
C2 C7 C6 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
N1 C19 H19 118.8 . . ?
N1 C19 C18 122.4(3) . . ?
C18 C19 H19 118.8 . . ?
C5 C6 C7 118.5(3) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
N1 C15 H15 118.5 . . ?
N1 C15 C16 123.0(3) . . ?
C16 C15 H15 118.5 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C9 C14 H14 119.9 . . ?
C9 C14 C13 120.1(3) . . ?
C13 C14 H14 119.9 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
N2 C20 H20 118.6 . . ?
N2 C20 C21 122.8(3) . . ?
C21 C20 H20 118.6 . . ?
C24 C23 H23 120.5 . . ?
C22 C23 C24 119.0(3) . . ?
C22 C23 H23 120.5 . . ?
C14 C13 H13 120.4 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C13 C12 Br2 119.0(3) . . ?
C11 C12 Br2 119.0(3) . . ?
C11 C12 C13 122.1(3) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 C10 118.5(3) . . ?
C12 C11 H11 120.7 . . ?
C23 C22 H22 120.8 . . ?
C23 C22 C21 118.5(3) . . ?
C21 C22 H22 120.8 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 H21 120.3 . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.7(3) . . ?
C18 C17 H17 120.6 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.9(3) . . ?
C17 C16 H16 120.6 . . ?
C19 C18 H18 120.4 . . ?
C17 C18 C19 119.2(3) . . ?
C17 C18 H18 120.4 . . ?

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
Zn1 O5 C8 O4 0.3(3) . . . . ?
Zn1 O5 C8 C9 179.5(2) . . . . ?
Zn1 O4 C8 O5 -0.4(3) . . . . ?
Zn1 O4 C8 C9 -179.5(2) . . . . ?
Zn1 O2 C1 O1 -10.0(5) . . . . ?
Zn1 O2 C1 C2 172.4(2) . . . . ?
Zn1 N1 C19 C18 -176.8(2) . . . . ?
Zn1 N1 C15 C16 176.9(2) . . . . ?
Zn1 N2 C24 C23 -179.8(2) . . . . ?
Zn1 N2 C20 C21 -179.8(3) . . . . ?
Br1 C5 C6 C7 -177.6(2) . . . . ?
Br1 C5 C4 C3 178.1(2) . . . . ?
Br2 C12 C11 C10 -178.9(2) . . . . ?
O5 C8 C9 C14 13.1(4) . . . . ?
O5 C8 C9 C10 -165.3(2) . . . . ?
O4 C8 C9 C14 -167.8(3) . . . . ?
O4 C8 C9 C10 13.9(4) . . . . ?
N1 C19 C18 C17 0.3(5) . . . . ?
N1 C15 C16 C17 -0.2(5) . . . . ?
N2 C24 C23 C22 0.0(5) . . . . ?
N2 C20 C21 C22 -0.5(6) . . . . ?
C8 C9 C14 C13 -178.8(3) . . . . ?
C8 C9 C10 C11 177.9(3) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C2 C7 C6 C5 -0.5(4) . . . . ?
C1 C2 C3 C4 -177.0(3) . . . . ?
C1 C2 C7 C6 177.4(2) . . . . ?
C9 C14 C13 C12 1.4(4) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C24 N2 C20 C21 1.9(5) . . . . ?
C24 C23 C22 C21 1.5(5) . . . . ?
C3 C2 C1 O2 162.8(2) . . . . ?
C3 C2 C1 O1 -15.0(4) . . . . ?
C3 C2 C7 C6 -0.5(4) . . . . ?
C7 C2 C1 O2 -15.1(3) . . . . ?
C7 C2 C1 O1 167.1(3) . . . . ?
C7 C2 C3 C4 1.0(4) . . . . ?
C19 N1 C15 C16 -0.7(4) . . . . ?
C6 C5 C4 C3 -0.6(5) . . . . ?
C15 N1 C19 C18 0.7(4) . . . . ?
C4 C5 C6 C7 1.1(5) . . . . ?
C14 C9 C10 C11 -0.5(4) . . . . ?
C14 C13 C12 Br2 178.0(2) . . . . ?
C14 C13 C12 C11 -1.5(5) . . . . ?
C10 C9 C14 C13 -0.5(4) . . . . ?
C20 N2 C24 C23 -1.6(4) . . . . ?
C23 C22 C21 C20 -1.2(5) . . . . ?
C13 C12 C11 C10 0.6(5) . . . . ?
C16 C17 C18 C19 -1.2(5) . . . . ?
C18 C17 C16 C15 1.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3s
_database_code_depnum_ccdc_archive 'CCDC 2411965'
loop_
_audit_author_name
_audit_author_address
'Paolo Pio Mazzeo'
;University of Parma
Italy
;
_audit_update_record             
;
2024-12-20 deposited with the CCDC.	2025-03-03 downloaded from the CCDC.
;
_audit_creation_date             2024-11-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 I2 N2 O5 Zn'
_chemical_formula_sum            'C24 H20 I2 N2 O5 Zn'
_chemical_formula_weight         735.59
_chemical_melting_point          ?
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'
I I -0.4742 1.8119 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   15.755(3)
_cell_length_b                   5.8553(8)
_cell_length_c                   27.436(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.130(7)
_cell_angle_gamma                90
_cell_volume                     2491.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9134
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      26.303
_cell_measurement_theta_min      2.408
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.502
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1663 before and 0.0870 after correction.
The Ratio of minimum to maximum transmission is 0.7141.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            68138
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.349
_diffrn_reflns_theta_min         2.408
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon III'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4875
_reflns_number_total             6214
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.312
_refine_diff_density_min         -1.809
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         6214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0278P)²+4.7620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0876
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C3(H3), C24(H24), C14(H14), C10(H10), C15(H15), C19(H19),
 C22(H22), C13(H13), C11(H11), C20(H20), C4(H4), C23(H23), C16(H16), C18(H18),
 C21(H21), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
I1 I 0.93136(2) 0.04663(6) 0.71238(2) 0.06892(11) Uani 1 1 d . . . . .
I2 I -0.15859(2) 0.75659(7) 0.54884(2) 0.07844(13) Uani 1 1 d . . . . .
Zn1 Zn 0.36406(2) 0.13201(6) 0.62425(2) 0.03076(10) Uani 1 1 d . . . . .
O3 O 0.3810(2) -0.2118(5) 0.63658(10) 0.0402(6) Uani 1 1 d . . . . .
O5 O 0.27958(14) 0.4323(4) 0.60007(9) 0.0425(6) Uani 1 1 d . . . . .
O4 O 0.22146(15) 0.1002(4) 0.61024(9) 0.0437(6) Uani 1 1 d . . . . .
O2 O 0.48916(15) 0.2073(5) 0.63961(10) 0.0480(6) Uani 1 1 d . . . . .
N2 N 0.36213(17) 0.2008(5) 0.70233(10) 0.0347(6) Uani 1 1 d . . . . .
O1 O 0.52700(17) 0.5678(5) 0.63057(11) 0.0577(7) Uani 1 1 d . . . . .
N1 N 0.37054(17) 0.0922(5) 0.54642(10) 0.0366(6) Uani 1 1 d . . . . .
C8 C 0.2140(2) 0.3073(6) 0.59911(11) 0.0353(7) Uani 1 1 d . . . . .
C1 C 0.5429(2) 0.3670(6) 0.64290(12) 0.0368(7) Uani 1 1 d . . . . .
C9 C 0.1261(2) 0.4103(6) 0.58507(11) 0.0348(7) Uani 1 1 d . . . . .
C2 C 0.63517(19) 0.2986(6) 0.66154(11) 0.0331(7) Uani 1 1 d . . . . .
C6 C 0.7381(2) 0.0203(6) 0.70020(13) 0.0413(8) Uani 1 1 d . . . . .
H6 H 0.750197 -0.119305 0.716070 0.050 Uiso 1 1 calc R U . . .
C7 C 0.6539(2) 0.0885(6) 0.68473(13) 0.0396(8) Uani 1 1 d . . . . .
H7 H 0.609144 -0.006915 0.689847 0.048 Uiso 1 1 calc R U . . .
C5 C 0.8041(2) 0.1614(6) 0.69187(13) 0.0402(8) Uani 1 1 d . . . . .
C3 C 0.7027(2) 0.4397(6) 0.65487(13) 0.0409(8) Uani 1 1 d . . . . .
H3 H 0.690889 0.582219 0.640297 0.049 Uiso 1 1 calc R U . . .
C12 C -0.0365(2) 0.6031(7) 0.56315(13) 0.0484(9) Uani 1 1 d . . . . .
C24 C 0.3285(2) 0.3868(6) 0.71910(13) 0.0416(8) Uani 1 1 d . . . . .
H24 H 0.303423 0.495296 0.696271 0.050 Uiso 1 1 calc R U . . .
C14 C 0.1150(2) 0.6244(7) 0.56346(13) 0.0446(8) Uani 1 1 d . . . . .
H14 H 0.162592 0.704249 0.556620 0.053 Uiso 1 1 calc R U . . .
C10 C 0.0542(2) 0.2938(7) 0.59520(13) 0.0441(8) Uani 1 1 d . . . . .
H10 H 0.061052 0.149523 0.609526 0.053 Uiso 1 1 calc R U . . .
C15 C 0.4064(2) 0.2598(7) 0.52431(13) 0.0452(9) Uani 1 1 d . . . . .
H15 H 0.425081 0.389636 0.542626 0.054 Uiso 1 1 calc R U . . .
C19 C 0.3432(2) -0.0901(7) 0.51929(14) 0.0479(9) Uani 1 1 d . . . . .
H19 H 0.317952 -0.208995 0.534095 0.057 Uiso 1 1 calc R U . . .
C22 C 0.3656(3) 0.2695(7) 0.80288(14) 0.0509(10) Uani 1 1 d . . . . .
H22 H 0.365257 0.290514 0.836444 0.061 Uiso 1 1 calc R U . . .
C13 C 0.0337(3) 0.7203(7) 0.55196(14) 0.0495(9) Uani 1 1 d . . . . .
H13 H 0.026402 0.862765 0.536801 0.059 Uiso 1 1 calc R U . . .
C11 C -0.0271(2) 0.3888(8) 0.58433(14) 0.0502(9) Uani 1 1 d . . . . .
H11 H -0.074763 0.309685 0.591184 0.060 Uiso 1 1 calc R U . . .
C20 C 0.3996(3) 0.0512(7) 0.73602(13) 0.0487(9) Uani 1 1 d . . . . .
H20 H 0.424725 -0.078474 0.725119 0.058 Uiso 1 1 calc R U . . .
C4 C 0.7877(2) 0.3714(7) 0.66962(14) 0.0447(8) Uani 1 1 d . . . . .
H4 H 0.832763 0.465900 0.664568 0.054 Uiso 1 1 calc R U . . .
C23 C 0.3289(3) 0.4271(7) 0.76871(14) 0.0488(9) Uani 1 1 d . . . . .
H23 H 0.304562 0.559780 0.778798 0.059 Uiso 1 1 calc R U . . .
C16 C 0.4172(3) 0.2502(8) 0.47552(14) 0.0535(10) Uani 1 1 d . . . . .
H16 H 0.442800 0.370678 0.461435 0.064 Uiso 1 1 calc R U . . .
C18 C 0.3508(3) -0.1109(8) 0.47018(15) 0.0577(11) Uani 1 1 d . . . . .
H18 H 0.329840 -0.239727 0.452144 0.069 Uiso 1 1 calc R U . . .
C21 C 0.4028(3) 0.0792(8) 0.78618(14) 0.0567(10) Uani 1 1 d . . . . .
H21 H 0.429891 -0.029063 0.808429 0.068 Uiso 1 1 calc R U . . .
C17 C 0.3896(3) 0.0614(8) 0.44837(14) 0.0588(11) Uani 1 1 d . . . . .
H17 H 0.396918 0.049485 0.415569 0.071 Uiso 1 1 calc R U . . .
H3A H 0.420(3) -0.270(7) 0.6359(15) 0.041(13) Uiso 1 1 d . . . . .
H3B H 0.345(3) -0.292(9) 0.6243(18) 0.068(16) Uiso 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
I1 C5 2.096(3) . ?
I2 C12 2.097(4) . ?
Zn1 O3 2.051(3) . ?
Zn1 O5 2.234(2) . ?
Zn1 O4 2.220(2) . ?
Zn1 O2 1.991(2) . ?
Zn1 N2 2.185(3) . ?
Zn1 N1 2.168(3) . ?
Zn1 C8 2.558(3) . ?
O3 H3A 0.71(4) . ?
O3 H3B 0.77(5) . ?
O5 C8 1.263(4) . ?
O4 C8 1.251(4) . ?
O2 C1 1.253(4) . ?
N2 C24 1.328(4) . ?
N2 C20 1.333(4) . ?
O1 C1 1.237(4) . ?
N1 C15 1.331(4) . ?
N1 C19 1.329(5) . ?
C8 C9 1.497(4) . ?
C1 C2 1.508(4) . ?
C9 C14 1.384(5) . ?
C9 C10 1.392(5) . ?
C2 C7 1.393(5) . ?
C2 C3 1.384(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(5) . ?
C6 C5 1.378(5) . ?
C7 H7 0.9300 . ?
C5 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(5) . ?
C12 C13 1.381(6) . ?
C12 C11 1.380(6) . ?
C24 H24 0.9300 . ?
C24 C23 1.380(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.383(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(5) . ?
C19 H19 0.9300 . ?
C19 C18 1.379(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.369(6) . ?
C22 C21 1.375(6) . ?
C13 H13 0.9300 . ?
C11 H11 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.378(5) . ?
C4 H4 0.9300 . ?
C23 H23 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.361(6) . ?
C18 H18 0.9300 . ?
C18 C17 1.371(6) . ?
C21 H21 0.9300 . ?
C17 H17 0.9300 . ?

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
O3 Zn1 O5 151.02(11) . . ?
O3 Zn1 O4 92.56(11) . . ?
O3 Zn1 N2 92.47(11) . . ?
O3 Zn1 N1 91.69(11) . . ?
O3 Zn1 C8 121.71(12) . . ?
O5 Zn1 C8 29.58(10) . . ?
O4 Zn1 O5 58.84(9) . . ?
O4 Zn1 C8 29.27(10) . . ?
O2 Zn1 O3 94.99(12) . . ?
O2 Zn1 O5 113.86(10) . . ?
O2 Zn1 O4 171.66(11) . . ?
O2 Zn1 N2 86.31(10) . . ?
O2 Zn1 N1 90.92(11) . . ?
O2 Zn1 C8 143.30(12) . . ?
N2 Zn1 O5 92.06(9) . . ?
N2 Zn1 O4 89.83(9) . . ?
N2 Zn1 C8 91.08(10) . . ?
N1 Zn1 O5 85.47(10) . . ?
N1 Zn1 O4 92.40(10) . . ?
N1 Zn1 N2 175.19(11) . . ?
N1 Zn1 C8 88.79(10) . . ?
Zn1 O3 H3A 124(3) . . ?
Zn1 O3 H3B 117(4) . . ?
H3A O3 H3B 106(5) . . ?
C8 O5 Zn1 89.6(2) . . ?
C8 O4 Zn1 90.6(2) . . ?
C1 O2 Zn1 144.2(2) . . ?
C24 N2 Zn1 124.5(2) . . ?
C24 N2 C20 116.9(3) . . ?
C20 N2 Zn1 118.6(2) . . ?
C15 N1 Zn1 117.8(2) . . ?
C19 N1 Zn1 124.8(2) . . ?
C19 N1 C15 117.3(3) . . ?
O5 C8 Zn1 60.84(17) . . ?
O5 C8 C9 119.2(3) . . ?
O4 C8 Zn1 60.17(17) . . ?
O4 C8 O5 121.0(3) . . ?
O4 C8 C9 119.8(3) . . ?
C9 C8 Zn1 179.3(2) . . ?
O2 C1 C2 115.1(3) . . ?
O1 C1 O2 126.0(3) . . ?
O1 C1 C2 118.8(3) . . ?
C14 C9 C8 121.1(3) . . ?
C14 C9 C10 118.9(3) . . ?
C10 C9 C8 120.0(3) . . ?
C7 C2 C1 120.3(3) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 C7 118.8(3) . . ?
C7 C6 H6 120.4 . . ?
C7 C6 C5 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C6 C5 I1 118.5(3) . . ?
C4 C5 I1 120.1(3) . . ?
C4 C5 C6 121.4(3) . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C13 C12 I2 119.3(3) . . ?
C11 C12 I2 119.7(3) . . ?
C11 C12 C13 121.0(3) . . ?
N2 C24 H24 118.4 . . ?
N2 C24 C23 123.3(3) . . ?
C23 C24 H24 118.4 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.5(4) . . ?
C13 C14 H14 119.8 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(4) . . ?
C11 C10 H10 119.5 . . ?
N1 C15 H15 118.4 . . ?
N1 C15 C16 123.1(4) . . ?
C16 C15 H15 118.4 . . ?
N1 C19 H19 118.5 . . ?
N1 C19 C18 122.9(4) . . ?
C18 C19 H19 118.5 . . ?
C23 C22 H22 120.9 . . ?
C23 C22 C21 118.1(3) . . ?
C21 C22 H22 120.9 . . ?
C12 C13 C14 119.5(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C12 C11 H11 120.5 . . ?
C10 C11 C12 119.0(4) . . ?
C10 C11 H11 120.5 . . ?
N2 C20 H20 118.4 . . ?
N2 C20 C21 123.3(4) . . ?
C21 C20 H20 118.4 . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C24 C23 H23 120.4 . . ?
C22 C23 C24 119.2(4) . . ?
C22 C23 H23 120.4 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.8(4) . . ?
C17 C16 H16 120.6 . . ?
C19 C18 H18 120.5 . . ?
C17 C18 C19 118.9(4) . . ?
C17 C18 H18 120.5 . . ?
C22 C21 C20 119.1(4) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C16 C17 C18 118.9(4) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?

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
I1 C5 C4 C3 177.8(3) . . . . ?
I2 C12 C13 C14 177.0(3) . . . . ?
I2 C12 C11 C10 -177.6(3) . . . . ?
Zn1 O5 C8 O4 0.0(3) . . . . ?
Zn1 O5 C8 C9 179.2(3) . . . . ?
Zn1 O4 C8 O5 0.0(3) . . . . ?
Zn1 O4 C8 C9 -179.2(3) . . . . ?
Zn1 O2 C1 O1 -7.7(7) . . . . ?
Zn1 O2 C1 C2 175.3(3) . . . . ?
Zn1 N2 C24 C23 -179.3(3) . . . . ?
Zn1 N2 C20 C21 179.3(3) . . . . ?
Zn1 N1 C15 C16 177.5(3) . . . . ?
Zn1 N1 C19 C18 -178.2(3) . . . . ?
O5 C8 C9 C14 13.5(5) . . . . ?
O5 C8 C9 C10 -164.3(3) . . . . ?
O4 C8 C9 C14 -167.3(3) . . . . ?
O4 C8 C9 C10 14.8(5) . . . . ?
O2 C1 C2 C7 -15.5(4) . . . . ?
O2 C1 C2 C3 162.8(3) . . . . ?
N2 C24 C23 C22 0.0(6) . . . . ?
N2 C20 C21 C22 0.3(7) . . . . ?
O1 C1 C2 C7 167.3(3) . . . . ?
O1 C1 C2 C3 -14.3(5) . . . . ?
N1 C15 C16 C17 0.3(6) . . . . ?
N1 C19 C18 C17 1.3(6) . . . . ?
C8 C9 C14 C13 -178.1(3) . . . . ?
C8 C9 C10 C11 177.5(3) . . . . ?
C1 C2 C7 C6 177.5(3) . . . . ?
C1 C2 C3 C4 -176.5(3) . . . . ?
C9 C14 C13 C12 1.4(6) . . . . ?
C9 C10 C11 C12 -0.1(6) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C6 C5 C4 C3 -0.8(6) . . . . ?
C7 C2 C3 C4 1.9(5) . . . . ?
C7 C6 C5 I1 -176.9(3) . . . . ?
C7 C6 C5 C4 1.7(6) . . . . ?
C5 C6 C7 C2 -0.9(5) . . . . ?
C3 C2 C7 C6 -0.9(5) . . . . ?
C24 N2 C20 C21 1.5(6) . . . . ?
C14 C9 C10 C11 -0.4(5) . . . . ?
C10 C9 C14 C13 -0.3(5) . . . . ?
C15 N1 C19 C18 0.1(5) . . . . ?
C15 C16 C17 C18 1.1(6) . . . . ?
C19 N1 C15 C16 -0.9(5) . . . . ?
C19 C18 C17 C16 -1.9(6) . . . . ?
C13 C12 C11 C10 1.2(6) . . . . ?
C11 C12 C13 C14 -1.9(6) . . . . ?
C20 N2 C24 C23 -1.7(5) . . . . ?
C23 C22 C21 C20 -2.0(6) . . . . ?
C21 C22 C23 C24 1.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1s
_database_code_depnum_ccdc_archive 'CCDC 2411966'
loop_
_audit_author_name
_audit_author_address
'Paolo Pio Mazzeo'
;University of Parma
Italy
;
_audit_update_record             
;
2024-12-20 deposited with the CCDC.	2025-03-03 downloaded from the CCDC.
;
_audit_creation_date             2024-11-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 Cl2 N2 O5 Zn'
_chemical_formula_sum            'C24 H20 Cl2 N2 O5 Zn'
_chemical_formula_weight         552.69
_chemical_melting_point          ?
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   15.130(4)
_cell_length_b                   5.8821(15)
_cell_length_c                   27.358(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.212(8)
_cell_angle_gamma                90
_cell_volume                     2388.3(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8250
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      22.812
_cell_measurement_theta_min      2.745
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.782
_exptl_absorpt_coefficient_mu    1.291
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1146 before and 0.0807 after correction.
The Ratio of minimum to maximum transmission is 0.8946.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0954
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            71946
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_min         2.419
_diffrn_ambient_temperature      299.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture Photon III'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4548
_reflns_number_total             5915
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         5915
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+1.4402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0976
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C15(H15), C13(H13), C6(H6), C20(H20), C14(H14), C10(H10),
 C4(H4), C19(H19), C18(H18), C17(H17), C16(H16), C11(H11), C21(H21), C24(H24),
 C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.63720(2) 0.37266(4) 0.37596(2) 0.03144(9) Uani 1 1 d . . . . .
Cl1 Cl 0.06609(5) 0.41539(16) 0.28155(4) 0.0822(3) Uani 1 1 d . . . . .
Cl2 Cl 1.17260(6) -0.1586(2) 0.45546(4) 0.0995(4) Uani 1 1 d . . . . .
O5 O 0.72897(11) 0.0681(3) 0.39951(7) 0.0465(4) Uani 1 1 d . . . . .
O4 O 0.78425(11) 0.4058(3) 0.38990(7) 0.0458(4) Uani 1 1 d . . . . .
O3 O 0.61933(13) 0.7147(3) 0.36403(7) 0.0406(4) Uani 1 1 d . . . . .
O1 O 0.46786(12) -0.0645(3) 0.36765(8) 0.0600(5) Uani 1 1 d . . . . .
O2 O 0.50574(11) 0.2993(3) 0.36159(6) 0.0478(4) Uani 1 1 d . . . . .
N2 N 0.63452(13) 0.4049(3) 0.45427(7) 0.0368(4) Uani 1 1 d . . . . .
N1 N 0.63419(13) 0.3028(3) 0.29740(7) 0.0373(4) Uani 1 1 d . . . . .
C2 C 0.35388(14) 0.2029(4) 0.33628(8) 0.0323(5) Uani 1 1 d . . . . .
C9 C 0.88925(15) 0.1080(4) 0.41535(8) 0.0357(5) Uani 1 1 d . . . . .
C7 C 0.33380(16) 0.4133(4) 0.31397(9) 0.0392(5) Uani 1 1 d . . . . .
H7 H 0.380306 0.512089 0.310740 0.047 Uiso 1 1 calc R U . . .
C1 C 0.45065(15) 0.1362(4) 0.35654(8) 0.0360(5) Uani 1 1 d . . . . .
C3 C 0.28416(16) 0.0571(4) 0.34087(9) 0.0409(5) Uani 1 1 d . . . . .
H3 H 0.297094 -0.084861 0.355456 0.049 Uiso 1 1 calc R U . . .
C8 C 0.79548(15) 0.2001(4) 0.40085(8) 0.0365(5) Uani 1 1 d . . . . .
C15 C 0.59359(19) 0.4511(5) 0.26365(9) 0.0511(7) Uani 1 1 d . . . . .
H15 H 0.567294 0.579480 0.274606 0.061 Uiso 1 1 calc R U . . .
C13 C 0.9933(2) -0.1870(5) 0.44879(10) 0.0539(7) Uani 1 1 d . . . . .
H13 H 1.004627 -0.329741 0.463272 0.065 Uiso 1 1 calc R U . . .
C6 C 0.24531(16) 0.4778(4) 0.29646(9) 0.0437(6) Uani 1 1 d . . . . .
H6 H 0.231889 0.618069 0.281134 0.052 Uiso 1 1 calc R U . . .
C20 C 0.66458(18) 0.5852(5) 0.48193(9) 0.0485(6) Uani 1 1 d . . . . .
H20 H 0.692106 0.702121 0.467564 0.058 Uiso 1 1 calc R U . . .
C14 C 0.90542(17) -0.1068(4) 0.43605(9) 0.0437(6) Uani 1 1 d . . . . .
H14 H 0.857655 -0.196785 0.441397 0.052 Uiso 1 1 calc R U . . .
C12 C 1.06322(18) -0.0546(6) 0.43988(10) 0.0562(7) Uani 1 1 d . . . . .
C10 C 0.96163(16) 0.2383(5) 0.40730(9) 0.0436(6) Uani 1 1 d . . . . .
H10 H 0.951337 0.382792 0.393568 0.052 Uiso 1 1 calc R U . . .
C4 C 0.19511(17) 0.1207(5) 0.32391(10) 0.0484(6) Uani 1 1 d . . . . .
H4 H 0.148253 0.023177 0.327217 0.058 Uiso 1 1 calc R U . . .
C19 C 0.66916(17) 0.1184(4) 0.28037(9) 0.0430(6) Uani 1 1 d . . . . .
H19 H 0.696527 0.010738 0.303291 0.052 Uiso 1 1 calc R U . . .
C18 C 0.66692(19) 0.0787(5) 0.23047(10) 0.0504(7) Uani 1 1 d . . . . .
H18 H 0.692313 -0.052652 0.220216 0.061 Uiso 1 1 calc R U . . .
C17 C 0.62698(19) 0.2345(5) 0.19644(9) 0.0523(7) Uani 1 1 d . . . . .
H17 H 0.625668 0.213678 0.162613 0.063 Uiso 1 1 calc R U . . .
C16 C 0.5887(2) 0.4230(5) 0.21331(10) 0.0596(8) Uani 1 1 d . . . . .
H16 H 0.559817 0.530812 0.190910 0.072 Uiso 1 1 calc R U . . .
C5 C 0.17765(16) 0.3298(5) 0.30224(10) 0.0458(6) Uani 1 1 d . . . . .
C11 C 1.04866(18) 0.1563(5) 0.41939(10) 0.0552(7) Uani 1 1 d . . . . .
H11 H 1.096726 0.244041 0.413619 0.066 Uiso 1 1 calc R U . . .
C21 C 0.6564(2) 0.6053(5) 0.53129(11) 0.0606(8) Uani 1 1 d . . . . .
H21 H 0.678126 0.733551 0.549656 0.073 Uiso 1 1 calc R U . . .
C24 C 0.59729(17) 0.2377(5) 0.47596(9) 0.0459(6) Uani 1 1 d . . . . .
H24 H 0.577450 0.109042 0.457254 0.055 Uiso 1 1 calc R U . . .
C22 C 0.6159(2) 0.4332(6) 0.55271(10) 0.0582(8) Uani 1 1 d . . . . .
H22 H 0.608491 0.443955 0.585584 0.070 Uiso 1 1 calc R U . . .
C23 C 0.58671(19) 0.2457(5) 0.52466(10) 0.0535(7) Uani 1 1 d . . . . .
H23 H 0.560037 0.125196 0.538377 0.064 Uiso 1 1 calc R U . . .
H3A H 0.657(2) 0.802(6) 0.3747(11) 0.059(10) Uiso 1 1 d . . . . .
H3B H 0.571(3) 0.786(7) 0.3666(14) 0.109(15) Uiso 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
Zn1 O5 2.2811(18) . ?
Zn1 O4 2.1916(18) . ?
Zn1 O3 2.0475(18) . ?
Zn1 O2 1.9982(17) . ?
Zn1 N2 2.1591(19) . ?
Zn1 N1 2.1798(19) . ?
Zn1 C8 2.568(2) . ?
Cl1 C5 1.747(2) . ?
Cl2 C12 1.738(3) . ?
O5 C8 1.266(3) . ?
O4 C8 1.250(3) . ?
O3 H3A 0.78(3) . ?
O3 H3B 0.86(4) . ?
O1 C1 1.234(3) . ?
O2 C1 1.261(3) . ?
N2 C20 1.331(3) . ?
N2 C24 1.329(3) . ?
N1 C15 1.330(3) . ?
N1 C19 1.330(3) . ?
C2 C7 1.387(3) . ?
C2 C1 1.513(3) . ?
C2 C3 1.384(3) . ?
C9 C8 1.498(3) . ?
C9 C14 1.387(3) . ?
C9 C10 1.389(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(4) . ?
C13 C12 1.374(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.376(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(4) . ?
C14 H14 0.9300 . ?
C12 C11 1.362(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.361(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.371(4) . ?
C16 H16 0.9300 . ?
C11 H11 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.372(4) . ?
C24 H24 0.9300 . ?
C24 C23 1.373(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.367(4) . ?
C23 H23 0.9300 . ?

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
O5 Zn1 C8 29.51(7) . . ?
O4 Zn1 O5 58.61(6) . . ?
O4 Zn1 C8 29.10(7) . . ?
O3 Zn1 O5 150.55(7) . . ?
O3 Zn1 O4 92.21(7) . . ?
O3 Zn1 N2 92.55(7) . . ?
O3 Zn1 N1 92.94(7) . . ?
O3 Zn1 C8 121.20(8) . . ?
O2 Zn1 O5 114.45(7) . . ?
O2 Zn1 O4 172.48(7) . . ?
O2 Zn1 O3 94.89(8) . . ?
O2 Zn1 N2 90.23(7) . . ?
O2 Zn1 N1 86.34(7) . . ?
O2 Zn1 C8 143.91(8) . . ?
N2 Zn1 O5 85.20(7) . . ?
N2 Zn1 O4 91.94(7) . . ?
N2 Zn1 N1 173.75(7) . . ?
N2 Zn1 C8 88.16(7) . . ?
N1 Zn1 O5 91.46(7) . . ?
N1 Zn1 O4 90.82(7) . . ?
N1 Zn1 C8 91.53(7) . . ?
C8 O5 Zn1 87.90(15) . . ?
C8 O4 Zn1 92.40(14) . . ?
Zn1 O3 H3A 122(2) . . ?
Zn1 O3 H3B 124(3) . . ?
H3A O3 H3B 102(3) . . ?
C1 O2 Zn1 142.89(17) . . ?
C20 N2 Zn1 124.33(17) . . ?
C24 N2 Zn1 118.01(16) . . ?
C24 N2 C20 117.6(2) . . ?
C15 N1 Zn1 118.62(17) . . ?
C19 N1 Zn1 124.45(16) . . ?
C19 N1 C15 116.9(2) . . ?
C7 C2 C1 120.4(2) . . ?
C3 C2 C7 119.1(2) . . ?
C3 C2 C1 120.4(2) . . ?
C14 C9 C8 121.4(2) . . ?
C14 C9 C10 119.1(2) . . ?
C10 C9 C8 119.6(2) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.7(2) . . ?
C6 C7 H7 119.6 . . ?
O1 C1 O2 126.7(2) . . ?
O1 C1 C2 118.7(2) . . ?
O2 C1 C2 114.5(2) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
O5 C8 Zn1 62.59(12) . . ?
O5 C8 C9 119.5(2) . . ?
O4 C8 Zn1 58.50(12) . . ?
O4 C8 O5 121.1(2) . . ?
O4 C8 C9 119.4(2) . . ?
C9 C8 Zn1 177.91(18) . . ?
N1 C15 H15 118.5 . . ?
N1 C15 C16 123.0(3) . . ?
C16 C15 H15 118.5 . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.7(3) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 C7 118.5(2) . . ?
C5 C6 H6 120.7 . . ?
N2 C20 H20 118.7 . . ?
N2 C20 C21 122.5(3) . . ?
C21 C20 H20 118.7 . . ?
C9 C14 C13 119.7(3) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C13 C12 Cl2 119.1(2) . . ?
C11 C12 Cl2 119.5(2) . . ?
C11 C12 C13 121.4(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 H4 120.7 . . ?
N1 C19 H19 118.3 . . ?
N1 C19 C18 123.4(2) . . ?
C18 C19 H19 118.3 . . ?
C19 C18 H18 120.5 . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 H18 120.5 . . ?
C18 C17 H17 120.8 . . ?
C18 C17 C16 118.3(2) . . ?
C16 C17 H17 120.8 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C6 C5 Cl1 118.3(2) . . ?
C4 C5 Cl1 119.5(2) . . ?
C4 C5 C6 122.2(2) . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.0(3) . . ?
C22 C21 H21 120.5 . . ?
N2 C24 H24 118.4 . . ?
N2 C24 C23 123.2(3) . . ?
C23 C24 H24 118.4 . . ?
C21 C22 H22 120.7 . . ?
C23 C22 C21 118.6(3) . . ?
C23 C22 H22 120.7 . . ?
C24 C23 H23 120.5 . . ?
C22 C23 C24 119.1(3) . . ?
C22 C23 H23 120.5 . . ?

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
Zn1 O5 C8 O4 -0.8(2) . . . . ?
Zn1 O5 C8 C9 179.78(18) . . . . ?
Zn1 O4 C8 O5 0.8(2) . . . . ?
Zn1 O4 C8 C9 -179.74(17) . . . . ?
Zn1 O2 C1 O1 12.3(4) . . . . ?
Zn1 O2 C1 C2 -169.94(18) . . . . ?
Zn1 N2 C20 C21 175.8(2) . . . . ?
Zn1 N2 C24 C23 -175.8(2) . . . . ?
Zn1 N1 C15 C16 179.5(2) . . . . ?
Zn1 N1 C19 C18 -179.6(2) . . . . ?
Cl2 C12 C11 C10 -179.7(2) . . . . ?
N2 C20 C21 C22 0.0(4) . . . . ?
N2 C24 C23 C22 -0.3(4) . . . . ?
N1 C15 C16 C17 0.1(5) . . . . ?
N1 C19 C18 C17 -0.1(4) . . . . ?
C2 C7 C6 C5 0.8(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C7 C2 C1 O1 -166.7(2) . . . . ?
C7 C2 C1 O2 15.3(3) . . . . ?
C7 C2 C3 C4 -0.7(4) . . . . ?
C7 C6 C5 Cl1 178.33(19) . . . . ?
C7 C6 C5 C4 -1.0(4) . . . . ?
C1 C2 C7 C6 -178.4(2) . . . . ?
C1 C2 C3 C4 177.7(2) . . . . ?
C3 C2 C7 C6 0.0(4) . . . . ?
C3 C2 C1 O1 14.9(3) . . . . ?
C3 C2 C1 O2 -163.1(2) . . . . ?
C3 C4 C5 Cl1 -179.0(2) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C8 C9 C14 C13 179.7(2) . . . . ?
C8 C9 C10 C11 -178.8(2) . . . . ?
C15 N1 C19 C18 1.6(4) . . . . ?
C13 C12 C11 C10 -0.1(4) . . . . ?
C20 N2 C24 C23 1.6(4) . . . . ?
C20 C21 C22 C23 1.3(4) . . . . ?
C14 C9 C8 O5 -12.0(3) . . . . ?
C14 C9 C8 O4 168.6(2) . . . . ?
C14 C9 C10 C11 0.3(4) . . . . ?
C14 C13 C12 Cl2 -179.4(2) . . . . ?
C14 C13 C12 C11 1.0(4) . . . . ?
C12 C13 C14 C9 -1.2(4) . . . . ?
C10 C9 C8 O5 167.0(2) . . . . ?
C10 C9 C8 O4 -12.4(3) . . . . ?
C10 C9 C14 C13 0.6(4) . . . . ?
C19 N1 C15 C16 -1.6(4) . . . . ?
C19 C18 C17 C16 -1.4(4) . . . . ?
C18 C17 C16 C15 1.4(5) . . . . ?
C21 C22 C23 C24 -1.2(4) . . . . ?
C24 N2 C20 C21 -1.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
