# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2281715'
loop_
_audit_author_name
_audit_author_address
'MUNIYANDI SANKARALINGAM'
;National Institute of Technology Calicut
India
;
_audit_update_record             
;
2023-07-15 deposited with the CCDC.	2023-09-14 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         ?
_chemical_formula_sum            'C15 H18 Cl N3 O3 Zn'
_chemical_formula_weight         389.14

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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.3813(4)
_cell_length_b                   14.5936(4)
_cell_length_c                   17.3975(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3143.52(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9579
_cell_measurement_theta_min      5.08
_cell_measurement_theta_max      69.43

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    3.899
_shelx_estimated_absorpt_T_min   0.607
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5516
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            66873
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0863
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.084
_diffrn_reflns_theta_max         69.621
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2954
_reflns_number_gt                2186
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+20.6714P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2954
_refine_ls_number_parameters     214
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1820
_refine_ls_wR_factor_gt          0.1544
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.095
_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 0.10724(6) 0.36802(5) 0.06622(5) 0.0390(3) Uani 1 1 d . . . . .
C1 C -0.1394(5) 0.4076(5) 0.1046(4) 0.0523(16) Uani 1 1 d . . . . .
H1 H -0.129423 0.464425 0.081507 0.063 Uiso 1 1 calc R U . . .
C2 C -0.2428(5) 0.3843(5) 0.1304(4) 0.0543(17) Uani 1 1 d . . . . .
H2 H -0.300008 0.424835 0.124123 0.065 Uiso 1 1 calc R U . . .
C3 C -0.2587(5) 0.3017(5) 0.1646(4) 0.0517(16) Uani 1 1 d . . . . .
H3 H -0.327305 0.284993 0.181211 0.062 Uiso 1 1 calc R U . . .
C4 C -0.1708(5) 0.2415(4) 0.1750(4) 0.0460(14) Uani 1 1 d . . . . .
C5 C -0.1807(5) 0.1554(5) 0.2110(4) 0.0536(16) Uani 1 1 d . . . . .
H5 H -0.247144 0.135931 0.229783 0.064 Uiso 1 1 calc R U . . .
C6 C -0.0929(5) 0.1014(5) 0.2179(4) 0.0534(17) Uani 1 1 d . . . . .
H6 H -0.100179 0.045335 0.242740 0.064 Uiso 1 1 calc R U . . .
C7 C 0.0101(5) 0.1264(4) 0.1892(4) 0.0480(15) Uani 1 1 d . . . . .
H7 H 0.068607 0.086978 0.194800 0.058 Uiso 1 1 calc R U . . .
C8 C 0.0228(4) 0.2097(4) 0.1526(4) 0.0413(13) Uani 1 1 d . . . . .
C9 C -0.0687(4) 0.2683(4) 0.1468(3) 0.0399(13) Uani 1 1 d . . . . .
C10 C 0.2024(4) 0.1946(4) 0.1011(3) 0.0385(12) Uani 1 1 d . . . . .
C11 C 0.2916(4) 0.2470(4) 0.0603(4) 0.0407(13) Uani 1 1 d . . . . .
H11A H 0.360876 0.226287 0.079625 0.049 Uiso 1 1 calc R U . . .
H11B H 0.288789 0.232842 0.005829 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3245(4) 0.3761(4) 0.1474(4) 0.0400(13) Uani 1 1 d . . . . .
H12A H 0.290168 0.338483 0.186302 0.048 Uiso 1 1 calc R U . . .
H12B H 0.303590 0.439222 0.156627 0.048 Uiso 1 1 calc R U . . .
C13 C 0.4461(5) 0.3679(4) 0.1556(4) 0.0495(15) Uani 1 1 d . . . . .
H13A H 0.467932 0.391573 0.205301 0.059 Uiso 1 1 calc R U . . .
H13B H 0.466594 0.303779 0.153216 0.059 Uiso 1 1 calc R U . . .
C14 C 0.4686(5) 0.3848(4) 0.0223(4) 0.0474(15) Uani 1 1 d . . . . .
H14A H 0.487487 0.320605 0.016733 0.057 Uiso 1 1 calc R U . . .
H14B H 0.507320 0.419117 -0.016755 0.057 Uiso 1 1 calc R U . . .
C15 C 0.3480(4) 0.3967(4) 0.0108(3) 0.0397(13) Uani 1 1 d . . . . .
H15A H 0.330453 0.461457 0.012510 0.048 Uiso 1 1 calc R U . . .
H15B H 0.328204 0.373805 -0.039630 0.048 Uiso 1 1 calc R U . . .
Cl1 Cl 0.07742(12) 0.35981(10) -0.06363(9) 0.0466(4) Uani 1 1 d . . . . .
N1 N -0.0550(4) 0.3525(3) 0.1116(3) 0.0431(11) Uani 1 1 d . . . . .
N2 N 0.1169(3) 0.2449(3) 0.1195(3) 0.0388(11) Uani 1 1 d . . . . .
N3 N 0.2843(3) 0.3477(3) 0.0702(3) 0.0356(10) Uani 1 1 d . . . . .
O1 O 0.1149(3) 0.5028(3) 0.0960(3) 0.0521(12) Uani 1 1 d D . . . .
H1B H 0.169(4) 0.537(5) 0.093(5) 0.078 Uiso 1 1 d D U . . .
H1A H 0.061(4) 0.536(5) 0.087(5) 0.078 Uiso 1 1 d D U . . .
O2 O 0.2147(3) 0.1096(3) 0.1097(3) 0.0504(11) Uani 1 1 d . . . . .
O3 O 0.5002(3) 0.4165(3) 0.0973(3) 0.0547(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N2 2.026(5) . ?
Zn1 O1 2.036(4) . ?
Zn1 N1 2.171(5) . ?
Zn1 N3 2.213(4) . ?
Zn1 Cl1 2.2921(18) . ?
C1 N1 1.324(7) . ?
C1 C2 1.398(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.410(9) . ?
C4 C9 1.412(8) . ?
C5 C6 1.347(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.417(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(8) . ?
C7 H7 0.9300 . ?
C8 N2 1.397(7) . ?
C8 C9 1.423(8) . ?
C9 N1 1.382(7) . ?
C10 O2 1.260(7) . ?
C10 N2 1.328(7) . ?
C10 C11 1.519(8) . ?
C11 N3 1.482(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N3 1.491(7) . ?
C12 C13 1.518(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.407(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O3 1.438(8) . ?
C14 C15 1.517(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N3 1.485(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O1 H1B 0.84(2) . ?
O1 H1A 0.84(2) . ?

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 O1 137.6(2) . . ?
N2 Zn1 N1 78.18(17) . . ?
O1 Zn1 N1 92.95(18) . . ?
N2 Zn1 N3 78.96(17) . . ?
O1 Zn1 N3 94.34(16) . . ?
N1 Zn1 N3 153.05(19) . . ?
N2 Zn1 Cl1 114.46(15) . . ?
O1 Zn1 Cl1 107.97(16) . . ?
N1 Zn1 Cl1 101.77(15) . . ?
N3 Zn1 Cl1 100.56(13) . . ?
N1 C1 C2 123.0(6) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 119.3(6) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.8(6) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 123.1(6) . . ?
C3 C4 C9 118.3(6) . . ?
C5 C4 C9 118.6(6) . . ?
C6 C5 C4 119.4(6) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 123.0(6) . . ?
C5 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
C8 C7 C6 119.4(6) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 N2 127.4(5) . . ?
C7 C8 C9 118.1(5) . . ?
N2 C8 C9 114.4(5) . . ?
N1 C9 C4 120.6(5) . . ?
N1 C9 C8 117.9(5) . . ?
C4 C9 C8 121.5(5) . . ?
O2 C10 N2 127.7(5) . . ?
O2 C10 C11 117.7(5) . . ?
N2 C10 C11 114.5(5) . . ?
N3 C11 C10 113.6(4) . . ?
N3 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
N3 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
N3 C12 C13 113.2(5) . . ?
N3 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
N3 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
O3 C13 C12 111.4(5) . . ?
O3 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
O3 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O3 C14 C15 110.5(5) . . ?
O3 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
O3 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N3 C15 C14 112.1(5) . . ?
N3 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
N3 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C1 N1 C9 118.9(5) . . ?
C1 N1 Zn1 129.3(4) . . ?
C9 N1 Zn1 111.5(3) . . ?
C10 N2 C8 124.2(5) . . ?
C10 N2 Zn1 115.2(4) . . ?
C8 N2 Zn1 117.7(4) . . ?
C11 N3 C15 111.4(4) . . ?
C11 N3 C12 111.1(4) . . ?
C15 N3 C12 108.4(4) . . ?
C11 N3 Zn1 101.0(3) . . ?
C15 N3 Zn1 116.1(3) . . ?
C12 N3 Zn1 108.8(3) . . ?
Zn1 O1 H1B 126(6) . . ?
Zn1 O1 H1A 119(6) . . ?
H1B O1 H1A 106(8) . . ?
C13 O3 C14 111.3(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
N1 C1 C2 C3 0.3(11) . . . . ?
C1 C2 C3 C4 1.1(10) . . . . ?
C2 C3 C4 C5 179.1(6) . . . . ?
C2 C3 C4 C9 -2.1(9) . . . . ?
C3 C4 C5 C6 179.3(6) . . . . ?
C9 C4 C5 C6 0.5(10) . . . . ?
C4 C5 C6 C7 -1.3(11) . . . . ?
C5 C6 C7 C8 0.5(11) . . . . ?
C6 C7 C8 N2 -178.6(6) . . . . ?
C6 C7 C8 C9 1.2(10) . . . . ?
C3 C4 C9 N1 1.6(9) . . . . ?
C5 C4 C9 N1 -179.5(6) . . . . ?
C3 C4 C9 C8 -177.7(6) . . . . ?
C5 C4 C9 C8 1.2(9) . . . . ?
C7 C8 C9 N1 178.6(6) . . . . ?
N2 C8 C9 N1 -1.5(8) . . . . ?
C7 C8 C9 C4 -2.0(9) . . . . ?
N2 C8 C9 C4 177.8(5) . . . . ?
O2 C10 C11 N3 -165.2(5) . . . . ?
N2 C10 C11 N3 18.6(7) . . . . ?
N3 C12 C13 O3 54.8(7) . . . . ?
O3 C14 C15 N3 -57.7(6) . . . . ?
C2 C1 N1 C9 -0.8(10) . . . . ?
C2 C1 N1 Zn1 173.1(5) . . . . ?
C4 C9 N1 C1 -0.2(9) . . . . ?
C8 C9 N1 C1 179.1(6) . . . . ?
C4 C9 N1 Zn1 -175.2(4) . . . . ?
C8 C9 N1 Zn1 4.2(7) . . . . ?
O2 C10 N2 C8 -0.1(10) . . . . ?
C11 C10 N2 C8 175.6(5) . . . . ?
O2 C10 N2 Zn1 -160.6(5) . . . . ?
C11 C10 N2 Zn1 15.1(6) . . . . ?
C7 C8 N2 C10 17.5(10) . . . . ?
C9 C8 N2 C10 -162.3(5) . . . . ?
C7 C8 N2 Zn1 177.6(5) . . . . ?
C9 C8 N2 Zn1 -2.2(7) . . . . ?
C10 C11 N3 C15 -161.4(5) . . . . ?
C10 C11 N3 C12 77.7(6) . . . . ?
C10 C11 N3 Zn1 -37.5(5) . . . . ?
C14 C15 N3 C11 -69.9(6) . . . . ?
C14 C15 N3 C12 52.6(6) . . . . ?
C14 C15 N3 Zn1 175.3(4) . . . . ?
C13 C12 N3 C11 71.6(6) . . . . ?
C13 C12 N3 C15 -51.1(6) . . . . ?
C13 C12 N3 Zn1 -178.1(4) . . . . ?
C12 C13 O3 C14 -57.9(6) . . . . ?
C15 C14 O3 C13 59.5(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 Cl1 0.93 2.66 3.552(7) 160.3 5_565 yes
C2 H2 O3 0.93 2.52 3.269(7) 137.6 1_455 yes
C7 H7 O2 0.93 2.36 2.895(8) 116.4 . yes
C11 H11A Cl1 0.97 2.97 3.868(5) 153.7 3 yes
C12 H12B O2 0.97 2.63 3.503(7) 150.5 7_665 yes
C14 H14A Cl1 0.97 2.97 3.882(6) 156.7 3 yes
O1 H1B O2 0.84(2) 1.81(3) 2.635(6) 167(8) 7_665 yes
O1 H1A Cl1 0.84(2) 2.33(2) 3.163(4) 175(8) 5_565 yes

_refine_diff_density_max         0.808
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_ZN(AqPr)Cl
_database_code_depnum_ccdc_archive 'CCDC 2281716'
loop_
_audit_author_name
_audit_author_address
'MUNIYANDI SANKARALINGAM'
;National Institute of Technology Calicut
India
;
_audit_update_record             
;
2023-07-15 deposited with the CCDC.	2023-09-14 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         ?
_chemical_formula_sum            'C17 H22 Cl N3 O Zn'
_chemical_formula_weight         385.19

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'
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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.818(3)
_cell_length_b                   13.426(6)
_cell_length_c                   16.796(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1763.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    7872
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      70.26
_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'



_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.092
_exptl_absorpt_coefficient_mu    3.379
_shelx_estimated_absorpt_T_min   0.374
_shelx_estimated_absorpt_T_max   0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4636
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a

_diffrn_radiation_source         'micro-focus sealed tube'

_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12951
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.215
_diffrn_reflns_theta_max         70.255
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3256
_reflns_number_gt                3133
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_max     0.937
_reflns_Friedel_fraction_full    0.956

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²+0.7463P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.12(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3256
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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_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 0.51164(7) 0.59923(4) 0.52974(3) 0.0411(2) Uani 1 1 d . . . . .
Cl1 Cl 0.35507(17) 0.46214(10) 0.50446(10) 0.0654(4) Uani 1 1 d . . . . .
C1 C 0.2704(8) 0.5864(5) 0.6809(4) 0.0673(16) Uani 1 1 d . . . . .
H1 H 0.202079 0.545579 0.649501 0.081 Uiso 1 1 calc R U . . .
C2 C 0.2182(10) 0.6066(7) 0.7603(4) 0.090(2) Uani 1 1 d . . . . .
H2 H 0.118377 0.578581 0.780325 0.107 Uiso 1 1 calc R U . . .
C3 C 0.3145(9) 0.6667(6) 0.8062(4) 0.0745(18) Uani 1 1 d . . . . .
H3 H 0.280277 0.680758 0.858054 0.089 Uiso 1 1 calc R U . . .
C4 C 0.4671(8) 0.7085(4) 0.7762(3) 0.0558(13) Uani 1 1 d . . . . .
C5 C 0.5112(7) 0.6834(3) 0.6963(2) 0.0429(9) Uani 1 1 d . . . . .
C6 C 0.6647(7) 0.7206(4) 0.6617(3) 0.0444(10) Uani 1 1 d . . . . .
C7 C 0.7649(8) 0.7822(5) 0.7066(3) 0.0608(14) Uani 1 1 d . . . . .
H7 H 0.865311 0.807875 0.685091 0.073 Uiso 1 1 calc R U . . .
C8 C 0.7173(10) 0.8074(5) 0.7859(3) 0.0693(17) Uani 1 1 d . . . . .
H8 H 0.787550 0.849617 0.815183 0.083 Uiso 1 1 calc R U . . .
C9 C 0.5737(9) 0.7720(5) 0.8197(3) 0.0631(15) Uani 1 1 d . . . . .
H9 H 0.545463 0.789636 0.871639 0.076 Uiso 1 1 calc R U . . .
C10 C 0.8085(6) 0.7244(3) 0.5346(3) 0.0416(9) Uani 1 1 d . . . . .
C11 C 0.8169(6) 0.6739(3) 0.4535(3) 0.0444(11) Uani 1 1 d . . . . .
H11A H 0.759481 0.715731 0.414712 0.053 Uiso 1 1 calc R U . . .
H11B H 0.935759 0.668244 0.437575 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6828(7) 0.5481(4) 0.3695(3) 0.0465(11) Uani 1 1 d . . . . .
H12A H 0.597540 0.596376 0.353108 0.056 Uiso 1 1 calc R U . . .
H12B H 0.626800 0.483651 0.371522 0.056 Uiso 1 1 calc R U . . .
C13 C 0.8193(8) 0.5437(5) 0.3055(3) 0.0574(13) Uani 1 1 d . . . . .
H13A H 0.894112 0.487499 0.315597 0.069 Uiso 1 1 calc R U . . .
H13B H 0.887799 0.603886 0.307624 0.069 Uiso 1 1 calc R U . . .
C14 C 0.7413(10) 0.5335(6) 0.2231(3) 0.0752(18) Uani 1 1 d . . . . .
H14A H 0.830793 0.530909 0.184043 0.113 Uiso 1 1 calc R U . . .
H14B H 0.675004 0.473336 0.220578 0.113 Uiso 1 1 calc R U . . .
H14C H 0.668697 0.589616 0.212613 0.113 Uiso 1 1 calc R U . . .
C15 C 0.8633(6) 0.5015(3) 0.4862(3) 0.0461(11) Uani 1 1 d . . . . .
H15A H 0.892588 0.523038 0.539624 0.055 Uiso 1 1 calc R U . . .
H15B H 0.967008 0.503615 0.454580 0.055 Uiso 1 1 calc R U . . .
C16 C 0.8023(7) 0.3952(4) 0.4902(3) 0.0563(12) Uani 1 1 d . . . . .
H16A H 0.782158 0.370628 0.436673 0.068 Uiso 1 1 calc R U . . .
H16B H 0.694961 0.392378 0.519036 0.068 Uiso 1 1 calc R U . . .
C17 C 0.9332(8) 0.3290(4) 0.5314(3) 0.0599(13) Uani 1 1 d . . . . .
H17A H 0.891308 0.261803 0.533092 0.090 Uiso 1 1 calc R U . . .
H17B H 1.038920 0.330840 0.502352 0.090 Uiso 1 1 calc R U . . .
H17C H 0.951832 0.352563 0.584612 0.090 Uiso 1 1 calc R U . . .
N1 N 0.4102(6) 0.6229(3) 0.6505(2) 0.0488(10) Uani 1 1 d . . . . .
N2 N 0.6960(5) 0.6861(3) 0.5836(2) 0.0412(8) Uani 1 1 d . . . . .
N3 N 0.7385(5) 0.5740(3) 0.4520(2) 0.0397(8) Uani 1 1 d . . . . .
O1 O 0.9028(5) 0.7984(3) 0.54646(19) 0.0515(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.062(3) 2_466 ?
Zn1 N2 2.063(4) . ?
Zn1 N1 2.201(4) . ?
Zn1 N3 2.228(4) . ?
Zn1 Cl1 2.2509(15) . ?
C1 N1 1.303(7) . ?
C1 C2 1.419(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.347(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.411(9) . ?
C3 H3 0.9300 . ?
C4 C9 1.399(8) . ?
C4 C5 1.426(6) . ?
C5 N1 1.369(6) . ?
C5 C6 1.423(7) . ?
C6 C7 1.365(7) . ?
C6 N2 1.413(6) . ?
C7 C8 1.425(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.345(9) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 O1 1.253(6) . ?
C10 N2 1.311(6) . ?
C10 C11 1.523(6) . ?
C11 N3 1.474(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N3 1.493(6) . ?
C12 C13 1.516(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.519(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N3 1.494(6) . ?
C15 C16 1.507(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.521(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 N2 100.59(15) 2_466 . ?
O1 Zn1 N1 109.08(15) 2_466 . ?
N2 Zn1 N1 76.44(15) . . ?
O1 Zn1 N3 93.76(14) 2_466 . ?
N2 Zn1 N3 77.70(14) . . ?
N1 Zn1 N3 148.09(15) . . ?
O1 Zn1 Cl1 101.75(12) 2_466 . ?
N2 Zn1 Cl1 157.65(12) . . ?
N1 Zn1 Cl1 95.52(12) . . ?
N3 Zn1 Cl1 101.43(10) . . ?
N1 C1 C2 122.5(7) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 119.5(6) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.4(6) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C9 C4 C3 124.0(5) . . ?
C9 C4 C5 119.5(5) . . ?
C3 C4 C5 116.5(6) . . ?
N1 C5 C6 117.7(4) . . ?
N1 C5 C4 122.0(5) . . ?
C6 C5 C4 120.3(5) . . ?
C7 C6 N2 127.7(5) . . ?
C7 C6 C5 118.1(4) . . ?
N2 C6 C5 114.2(4) . . ?
C6 C7 C8 120.6(6) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 122.0(6) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C4 119.5(5) . . ?
C8 C9 H9 120.3 . . ?
C4 C9 H9 120.3 . . ?
O1 C10 N2 127.3(4) . . ?
O1 C10 C11 118.1(4) . . ?
N2 C10 C11 114.6(4) . . ?
N3 C11 C10 113.7(4) . . ?
N3 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
N3 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N3 C12 C13 117.5(4) . . ?
N3 C12 H12A 107.9 . . ?
C13 C12 H12A 107.9 . . ?
N3 C12 H12B 107.9 . . ?
C13 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
C12 C13 C14 111.5(5) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C16 115.4(4) . . ?
N3 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
N3 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
C15 C16 C17 111.2(5) . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 N1 C5 119.1(5) . . ?
C1 N1 Zn1 127.6(4) . . ?
C5 N1 Zn1 113.3(3) . . ?
C10 N2 C6 124.8(4) . . ?
C10 N2 Zn1 114.5(3) . . ?
C6 N2 Zn1 118.2(3) . . ?
C11 N3 C12 110.5(3) . . ?
C11 N3 C15 108.3(4) . . ?
C12 N3 C15 113.3(4) . . ?
C11 N3 Zn1 100.5(3) . . ?
C12 N3 Zn1 110.3(3) . . ?
C15 N3 Zn1 113.1(3) . . ?
C10 O1 Zn1 132.2(3) . 2_566 ?

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
N1 C1 C2 C3 0.9(13) . . . . ?
C1 C2 C3 C4 -0.7(12) . . . . ?
C2 C3 C4 C9 179.5(7) . . . . ?
C2 C3 C4 C5 -0.1(10) . . . . ?
C9 C4 C5 N1 -178.9(5) . . . . ?
C3 C4 C5 N1 0.8(7) . . . . ?
C9 C4 C5 C6 1.6(7) . . . . ?
C3 C4 C5 C6 -178.8(5) . . . . ?
N1 C5 C6 C7 179.0(5) . . . . ?
C4 C5 C6 C7 -1.4(7) . . . . ?
N1 C5 C6 N2 -2.4(6) . . . . ?
C4 C5 C6 N2 177.2(4) . . . . ?
N2 C6 C7 C8 -177.9(5) . . . . ?
C5 C6 C7 C8 0.5(9) . . . . ?
C6 C7 C8 C9 0.2(10) . . . . ?
C7 C8 C9 C4 0.0(10) . . . . ?
C3 C4 C9 C8 179.5(6) . . . . ?
C5 C4 C9 C8 -0.9(8) . . . . ?
O1 C10 C11 N3 164.6(4) . . . . ?
N2 C10 C11 N3 -17.7(6) . . . . ?
N3 C12 C13 C14 -170.6(5) . . . . ?
N3 C15 C16 C17 -175.8(4) . . . . ?
C2 C1 N1 C5 -0.2(10) . . . . ?
C2 C1 N1 Zn1 179.6(6) . . . . ?
C6 C5 N1 C1 178.9(5) . . . . ?
C4 C5 N1 C1 -0.7(7) . . . . ?
C6 C5 N1 Zn1 -0.9(5) . . . . ?
C4 C5 N1 Zn1 179.5(4) . . . . ?
O1 C10 N2 C6 -2.2(8) . . . . ?
C11 C10 N2 C6 -179.7(4) . . . . ?
O1 C10 N2 Zn1 159.5(4) . . . . ?
C11 C10 N2 Zn1 -18.0(5) . . . . ?
C7 C6 N2 C10 -15.7(8) . . . . ?
C5 C6 N2 C10 165.9(4) . . . . ?
C7 C6 N2 Zn1 -176.7(5) . . . . ?
C5 C6 N2 Zn1 4.8(5) . . . . ?
C10 C11 N3 C12 155.5(4) . . . . ?
C10 C11 N3 C15 -79.9(5) . . . . ?
C10 C11 N3 Zn1 39.0(4) . . . . ?
C13 C12 N3 C11 60.7(6) . . . . ?
C13 C12 N3 C15 -61.1(5) . . . . ?
C13 C12 N3 Zn1 170.9(4) . . . . ?
C16 C15 N3 C11 179.2(4) . . . . ?
C16 C15 N3 C12 -57.8(6) . . . . ?
C16 C15 N3 Zn1 68.7(5) . . . . ?
N2 C10 O1 Zn1 -152.4(4) . . . 2_566 ?
C11 C10 O1 Zn1 25.0(6) . . . 2_566 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 Cl1 0.93 2.94 3.466(7) 117.5 . yes
C7 H7 O1 0.93 2.35 2.905(7) 118.0 . yes
C11 H11A N1 0.97 2.70 3.320(6) 122.4 2_566 yes
C16 H16B Cl1 0.97 2.83 3.619(6) 139.2 . yes

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.069

