# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 2289514'
loop_
_audit_author_name
_audit_author_address
'Dr. Tania Chowdhury'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2023-12-10 deposited with the CCDC.	2024-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H22 Cl2 N2 O Zn, H2 O'
_chemical_formula_sum            'C15 H24 Cl2 N2 O2 Zn'
_chemical_formula_weight         400.63

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.042(4)
_cell_length_b                   10.150(5)
_cell_length_c                   11.002(5)
_cell_angle_alpha                101.564(17)
_cell_angle_beta                 98.128(15)
_cell_angle_gamma                109.610(16)
_cell_volume                     907.8(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    145(2)
_cell_measurement_reflns_used    5340
_cell_measurement_theta_max      25.24
_cell_measurement_theta_min      2.21

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.654
_shelx_estimated_absorpt_T_min   0.595
_shelx_estimated_absorpt_T_max   0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4388
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
;

_diffrn_ambient_temperature      145(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7973
_diffrn_reflns_av_unetI/netI     0.0962
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.209
_diffrn_reflns_theta_max         24.403
_diffrn_reflns_theta_full        24.403
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             7973
_reflns_number_gt                7240
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'SAINT V8.38A (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component perfect 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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7973
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0895
_refine_ls_wR_factor_ref         0.2780
_refine_ls_wR_factor_gt          0.2628
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.163
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.004

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 0.37828(9) 0.71572(8) 0.59990(7) 0.0190(4) Uani 1 1 d . . . . .
Cl1 Cl 0.5765(2) 0.7505(2) 0.76238(18) 0.0335(6) Uani 1 1 d . . . . .
Cl2 Cl 0.1697(2) 0.7707(2) 0.65998(19) 0.0278(6) Uani 1 1 d . . . . .
N1 N 0.2961(7) 0.5068(7) 0.4888(6) 0.0220(14) Uani 1 1 d . . . . .
N2 N 0.1670(7) 0.2577(7) 0.7018(6) 0.0193(14) Uani 1 1 d . . . . .
H2 H 0.188448 0.180261 0.643703 0.023 Uiso 1 1 calc R U . . .
O1 O 0.4355(6) 0.8036(5) 0.4612(4) 0.0205(12) Uani 1 1 d . . . . .
C1 C 0.3184(10) 0.8583(9) 0.0302(8) 0.0271(18) Uani 1 1 d . . . . .
H1A H 0.211929 0.839798 -0.020814 0.041 Uiso 1 1 calc R U . . .
H1B H 0.386677 0.836647 -0.026205 0.041 Uiso 1 1 calc R U . . .
H1C H 0.368067 0.960408 0.079048 0.041 Uiso 1 1 calc R U . . .
C2 C 0.3003(8) 0.7621(9) 0.1214(7) 0.0214(17) Uani 1 1 d . . . . .
C3 C 0.2089(9) 0.6130(9) 0.0766(7) 0.0242(18) Uani 1 1 d . . . . .
H3 H 0.157393 0.571263 -0.011021 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1937(9) 0.5265(8) 0.1607(7) 0.0235(17) Uani 1 1 d . . . . .
H4 H 0.133618 0.425183 0.128563 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2649(8) 0.5841(8) 0.2933(7) 0.0174(16) Uani 1 1 d . . . . .
C6 C 0.3589(7) 0.7377(8) 0.3403(7) 0.0152(15) Uani 1 1 d . . . . .
C7 C 0.3734(7) 0.8244(8) 0.2512(7) 0.0158(15) Uani 1 1 d . . . . .
H7 H 0.433540 0.925892 0.280639 0.019 Uiso 1 1 calc R U . . .
C8 C 0.2469(8) 0.4787(8) 0.3669(7) 0.0183(16) Uani 1 1 d . . . . .
H8 H 0.193941 0.379393 0.321292 0.022 Uiso 1 1 calc R U . . .
C9 C 0.2831(10) 0.3831(8) 0.5434(7) 0.0233(17) Uani 1 1 d . . . . .
H9A H 0.390674 0.396486 0.591344 0.028 Uiso 1 1 calc R U . . .
H9B H 0.243997 0.292371 0.473988 0.028 Uiso 1 1 calc R U . . .
C10 C 0.1661(9) 0.3716(9) 0.6327(7) 0.0234(17) Uani 1 1 d . . . . .
H10A H 0.197691 0.466545 0.695493 0.028 Uiso 1 1 calc R U . . .
H10B H 0.055840 0.346298 0.582633 0.028 Uiso 1 1 calc R U . . .
C11 C 0.0021(8) 0.1889(9) 0.7276(8) 0.0246(18) Uani 1 1 d . . . . .
H11A H -0.080189 0.147857 0.646413 0.030 Uiso 1 1 calc R U . . .
H11B H -0.024402 0.263662 0.782876 0.030 Uiso 1 1 calc R U . . .
C12 C -0.0007(9) 0.0692(8) 0.7927(8) 0.0258(18) Uani 1 1 d . . . . .
H12A H -0.108002 0.027321 0.811502 0.031 Uiso 1 1 calc R U . . .
H12B H 0.017197 -0.009046 0.734329 0.031 Uiso 1 1 calc R U . . .
C13 C 0.1279(10) 0.1264(10) 0.9155(8) 0.034(2) Uani 1 1 d . . . . .
H13A H 0.127399 0.045577 0.953191 0.041 Uiso 1 1 calc R U . . .
H13B H 0.104531 0.197976 0.977335 0.041 Uiso 1 1 calc R U . . .
C14 C 0.2935(10) 0.1982(10) 0.8888(8) 0.031(2) Uani 1 1 d . . . . .
H14A H 0.375244 0.241538 0.970300 0.037 Uiso 1 1 calc R U . . .
H14B H 0.321922 0.123473 0.835588 0.037 Uiso 1 1 calc R U . . .
C15 C 0.2971(9) 0.3164(9) 0.8204(7) 0.0252(18) Uani 1 1 d . . . . .
H15A H 0.282866 0.397518 0.877927 0.030 Uiso 1 1 calc R U . . .
H15B H 0.403237 0.354640 0.798716 0.030 Uiso 1 1 calc R U . . .
O2 O -0.2478(6) -0.0521(6) 0.4518(5) 0.0237(12) Uani 1 1 d . . . . .
H12 H -0.248274 0.007006 0.407460 0.035 Uiso 1 1 d R U . . .
H11 H -0.353526 -0.100178 0.455111 0.035 Uiso 1 1 d 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 1.963(5) . ?
Zn1 N1 2.047(6) . ?
Zn1 Cl1 2.225(2) . ?
Zn1 Cl2 2.284(2) . ?
N1 C8 1.293(10) . ?
N1 C9 1.474(9) . ?
N2 C15 1.492(10) . ?
N2 C10 1.506(9) . ?
N2 C11 1.515(9) . ?
N2 H2 1.0000 . ?
O1 C6 1.330(9) . ?
C1 C2 1.522(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.401(11) . ?
C2 C7 1.402(10) . ?
C3 C4 1.388(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.423(11) . ?
C4 H4 0.9500 . ?
C5 C8 1.448(10) . ?
C5 C6 1.443(10) . ?
C6 C7 1.434(10) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.535(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.524(11) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.518(12) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.529(12) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.533(11) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O2 H12 0.8467 . ?
O2 H11 0.9257 . ?

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 N1 94.6(2) . . ?
O1 Zn1 Cl1 117.84(16) . . ?
N1 Zn1 Cl1 110.01(19) . . ?
O1 Zn1 Cl2 108.49(16) . . ?
N1 Zn1 Cl2 110.42(18) . . ?
Cl1 Zn1 Cl2 113.82(8) . . ?
C8 N1 C9 117.5(6) . . ?
C8 N1 Zn1 120.2(5) . . ?
C9 N1 Zn1 122.2(5) . . ?
C15 N2 C10 112.3(6) . . ?
C15 N2 C11 112.1(5) . . ?
C10 N2 C11 109.6(6) . . ?
C15 N2 H2 107.6 . . ?
C10 N2 H2 107.6 . . ?
C11 N2 H2 107.6 . . ?
C6 O1 Zn1 121.9(4) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 120.2(7) . . ?
C3 C2 C1 120.4(7) . . ?
C7 C2 C1 119.5(7) . . ?
C4 C3 C2 119.8(7) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 122.3(7) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C8 115.7(7) . . ?
C4 C5 C6 118.2(6) . . ?
C8 C5 C6 125.9(6) . . ?
O1 C6 C7 117.8(6) . . ?
O1 C6 C5 123.9(6) . . ?
C7 C6 C5 118.3(6) . . ?
C2 C7 C6 121.2(7) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
N1 C8 C5 126.2(7) . . ?
N1 C8 H8 116.9 . . ?
C5 C8 H8 116.9 . . ?
N1 C9 C10 110.1(6) . . ?
N1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
N2 C10 C9 110.8(6) . . ?
N2 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C12 110.2(6) . . ?
N2 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
N2 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 111.4(7) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 109.9(7) . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C13 111.9(7) . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N2 C15 C14 110.9(7) . . ?
N2 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
H12 O2 H11 107.3 . . ?

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
C7 C2 C3 C4 -1.4(11) . . . . ?
C1 C2 C3 C4 179.9(7) . . . . ?
C2 C3 C4 C5 1.6(12) . . . . ?
C3 C4 C5 C8 -176.1(7) . . . . ?
C3 C4 C5 C6 -1.4(11) . . . . ?
Zn1 O1 C6 C7 161.7(5) . . . . ?
Zn1 O1 C6 C5 -19.5(9) . . . . ?
C4 C5 C6 O1 -177.8(7) . . . . ?
C8 C5 C6 O1 -3.7(11) . . . . ?
C4 C5 C6 C7 1.0(10) . . . . ?
C8 C5 C6 C7 175.2(7) . . . . ?
C3 C2 C7 C6 1.1(10) . . . . ?
C1 C2 C7 C6 179.8(6) . . . . ?
O1 C6 C7 C2 178.0(6) . . . . ?
C5 C6 C7 C2 -0.9(10) . . . . ?
C9 N1 C8 C5 -172.9(7) . . . . ?
Zn1 N1 C8 C5 9.9(10) . . . . ?
C4 C5 C8 N1 -177.1(7) . . . . ?
C6 C5 C8 N1 8.6(12) . . . . ?
C8 N1 C9 C10 -116.3(7) . . . . ?
Zn1 N1 C9 C10 60.9(8) . . . . ?
C15 N2 C10 C9 86.0(8) . . . . ?
C11 N2 C10 C9 -148.7(6) . . . . ?
N1 C9 C10 N2 -173.0(6) . . . . ?
C15 N2 C11 C12 -57.0(8) . . . . ?
C10 N2 C11 C12 177.7(6) . . . . ?
N2 C11 C12 C13 57.2(9) . . . . ?
C11 C12 C13 C14 -56.2(9) . . . . ?
C12 C13 C14 C15 54.7(10) . . . . ?
C10 N2 C15 C14 179.4(6) . . . . ?
C11 N2 C15 C14 55.6(8) . . . . ?
C13 C14 C15 N2 -54.6(9) . . . . ?

_refine_diff_density_max         2.432
_refine_diff_density_min         -1.710
_refine_diff_density_rms         0.202



####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2289515'
loop_
_audit_author_name
_audit_author_address
'Dr. Tania Chowdhury'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2023-12-10 deposited with the CCDC.	2024-01-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_I                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.959 Why?  
RESPONSE: Diffraction data collected with Cu-K\a radiation by rotation around   
     the spindle axis only
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 Cl2 N3 O Zn'
_chemical_formula_sum            'C14 H21 Cl2 N3 O Zn'
_chemical_formula_weight         383.61

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.7511(11)
_cell_length_b                   18.385(2)
_cell_length_c                   10.2906(11)
_cell_angle_alpha                90
_cell_angle_beta                 113.811(3)
_cell_angle_gamma                90
_cell_volume                     1687.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      5.70
_cell_measurement_theta_max      70.10

_exptl_crystal_description       needle
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    4.945
_shelx_estimated_absorpt_T_min   0.255
_shelx_estimated_absorpt_T_max   0.470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.401
_exptl_absorpt_correction_T_max  0.610
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31610
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.801
_diffrn_reflns_theta_max         70.261
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             3075
_reflns_number_gt                3056
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_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)+(0.0863P)²+2.7613P] 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         3075
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1463
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_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 0.30060(5) 0.40226(2) 0.59616(4) 0.0212(2) Uani 1 1 d . . . . .
Cl1 Cl 0.15245(9) 0.39002(4) 0.71672(9) 0.0286(2) Uani 1 1 d . . . . .
Cl2 Cl 0.53882(9) 0.38671(5) 0.74677(8) 0.0347(3) Uani 1 1 d . . . . .
N1 N 0.2638(3) 0.49493(14) 0.4846(3) 0.0206(5) Uani 1 1 d . . . . .
N2 N 0.4136(3) 0.63616(13) 0.7688(2) 0.0166(5) Uani 1 1 d . . . . .
N3 N 0.6127(3) 0.70958(14) 1.0227(3) 0.0187(5) Uani 1 1 d . . . . .
H3A H 0.628(4) 0.678(2) 1.089(4) 0.022 Uiso 1 1 d . U . . .
H3B H 0.661(4) 0.757(2) 1.049(4) 0.022 Uiso 1 1 d . U . . .
O1 O 0.2406(2) 0.33843(12) 0.4303(2) 0.0224(5) Uani 1 1 d . . . . .
C1 C -0.1036(3) 0.26258(19) -0.0418(3) 0.0276(7) Uani 1 1 d . . . . .
H1A H -0.206891 0.275301 -0.104454 0.041 Uiso 1 1 calc R U . . .
H1B H -0.103088 0.216561 0.006482 0.041 Uiso 1 1 calc R U . . .
H1C H -0.043705 0.257393 -0.098129 0.041 Uiso 1 1 calc R U . . .
C2 C -0.0377(3) 0.32186(17) 0.0673(3) 0.0180(6) Uani 1 1 d . . . . .
C3 C -0.0778(3) 0.39451(17) 0.0320(3) 0.0201(6) Uani 1 1 d . . . . .
H3 H -0.150019 0.406812 -0.059766 0.024 Uiso 1 1 calc R U . . .
C4 C -0.0121(3) 0.44802(17) 0.1309(3) 0.0183(6) Uani 1 1 d . . . . .
H4 H -0.041306 0.497104 0.105938 0.022 Uiso 1 1 calc R U . . .
C5 C 0.0968(3) 0.43296(16) 0.2677(3) 0.0160(6) Uani 1 1 d . . . . .
C6 C 0.1361(3) 0.35891(16) 0.3047(3) 0.0151(5) Uani 1 1 d . . . . .
C7 C 0.0661(3) 0.30554(16) 0.2030(3) 0.0170(6) Uani 1 1 d . . . . .
H7 H 0.090383 0.255985 0.227810 0.020 Uiso 1 1 calc R U . . .
C8 C 0.1691(3) 0.49547(16) 0.3535(3) 0.0195(6) Uani 1 1 d . . . . .
H8 H 0.144170 0.541686 0.308812 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3369(4) 0.56315(18) 0.5497(3) 0.0250(7) Uani 1 1 d . . . . .
H9A H 0.291556 0.603992 0.483439 0.030 Uiso 1 1 calc R U . . .
H9B H 0.444704 0.560865 0.568631 0.030 Uiso 1 1 calc R U . . .
C10 C 0.3190(3) 0.57638(17) 0.6887(3) 0.0208(6) Uani 1 1 d . . . . .
H10A H 0.212849 0.587805 0.667476 0.025 Uiso 1 1 calc R U . . .
H10B H 0.346002 0.531585 0.746965 0.025 Uiso 1 1 calc R U . . .
C11 C 0.3611(3) 0.66127(17) 0.8757(3) 0.0200(6) Uani 1 1 d . . . . .
H11A H 0.371271 0.621424 0.943636 0.024 Uiso 1 1 calc R U . . .
H11B H 0.253679 0.674363 0.828670 0.024 Uiso 1 1 calc R U . . .
C12 C 0.4495(3) 0.72638(17) 0.9551(3) 0.0200(6) Uani 1 1 d . . . . .
H12A H 0.432287 0.767635 0.888473 0.024 Uiso 1 1 calc R U . . .
H12B H 0.414380 0.741010 1.029065 0.024 Uiso 1 1 calc R U . . .
C13 C 0.6669(3) 0.67725(19) 0.9190(3) 0.0245(7) Uani 1 1 d . . . . .
H13A H 0.772025 0.661079 0.969714 0.029 Uiso 1 1 calc R U . . .
H13B H 0.664190 0.714629 0.848763 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5707(3) 0.61321(18) 0.8426(3) 0.0231(7) Uani 1 1 d . . . . .
H14A H 0.607185 0.593202 0.773083 0.028 Uiso 1 1 calc R U . . .
H14B H 0.578014 0.574479 0.911993 0.028 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 1.956(2) . ?
Zn1 N1 2.004(3) . ?
Zn1 Cl2 2.2300(9) . ?
Zn1 Cl1 2.2636(9) . ?
N1 C8 1.291(4) . ?
N1 C9 1.464(4) . ?
N2 C10 1.458(4) . ?
N2 C11 1.463(3) . ?
N2 C14 1.470(4) . ?
N3 C12 1.489(4) . ?
N3 C13 1.492(4) . ?
N3 H3A 0.86(4) . ?
N3 H3B 0.97(4) . ?
O1 C6 1.337(3) . ?
C1 C2 1.509(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.387(4) . ?
C2 C3 1.398(4) . ?
C3 C4 1.374(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.424(4) . ?
C5 C8 1.448(4) . ?
C6 C7 1.396(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.529(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.508(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.513(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

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 N1 95.10(9) . . ?
O1 Zn1 Cl2 112.96(7) . . ?
N1 Zn1 Cl2 113.72(8) . . ?
O1 Zn1 Cl1 112.73(7) . . ?
N1 Zn1 Cl1 113.10(8) . . ?
Cl2 Zn1 Cl1 108.82(4) . . ?
C8 N1 C9 118.8(3) . . ?
C8 N1 Zn1 119.5(2) . . ?
C9 N1 Zn1 121.66(19) . . ?
C10 N2 C11 109.2(2) . . ?
C10 N2 C14 111.4(2) . . ?
C11 N2 C14 108.0(2) . . ?
C12 N3 C13 111.6(2) . . ?
C12 N3 H3A 109(3) . . ?
C13 N3 H3A 108(3) . . ?
C12 N3 H3B 104(2) . . ?
C13 N3 H3B 106(2) . . ?
H3A N3 H3B 118(3) . . ?
C6 O1 Zn1 121.15(18) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.8(3) . . ?
C7 C2 C1 120.7(3) . . ?
C3 C2 C1 120.4(3) . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 122.6(3) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C6 118.0(3) . . ?
C4 C5 C8 116.1(3) . . ?
C6 C5 C8 125.7(3) . . ?
O1 C6 C7 118.6(3) . . ?
O1 C6 C5 123.1(3) . . ?
C7 C6 C5 118.3(3) . . ?
C2 C7 C6 122.7(3) . . ?
C2 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
N1 C8 C5 126.8(3) . . ?
N1 C8 H8 116.6 . . ?
C5 C8 H8 116.6 . . ?
N1 C9 C10 110.2(3) . . ?
N1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N2 C10 C9 111.3(2) . . ?
N2 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N2 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N2 C11 C12 111.2(2) . . ?
N2 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N3 C12 C11 111.0(2) . . ?
N3 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
N3 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N3 C13 C14 110.9(2) . . ?
N3 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.0 . . ?
N2 C14 C13 110.1(3) . . ?
N2 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
N2 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.2 . . ?

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
C7 C2 C3 C4 1.2(4) . . . . ?
C1 C2 C3 C4 -177.4(3) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -1.8(4) . . . . ?
C3 C4 C5 C8 172.6(3) . . . . ?
Zn1 O1 C6 C7 -161.3(2) . . . . ?
Zn1 O1 C6 C5 21.1(4) . . . . ?
C4 C5 C6 O1 178.3(3) . . . . ?
C8 C5 C6 O1 4.6(4) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C8 C5 C6 C7 -173.0(3) . . . . ?
C3 C2 C7 C6 -2.3(4) . . . . ?
C1 C2 C7 C6 176.4(3) . . . . ?
O1 C6 C7 C2 -176.4(2) . . . . ?
C5 C6 C7 C2 1.3(4) . . . . ?
C9 N1 C8 C5 173.8(3) . . . . ?
Zn1 N1 C8 C5 -8.9(4) . . . . ?
C4 C5 C8 N1 174.8(3) . . . . ?
C6 C5 C8 N1 -11.4(5) . . . . ?
C8 N1 C9 C10 127.9(3) . . . . ?
Zn1 N1 C9 C10 -49.3(3) . . . . ?
C11 N2 C10 C9 162.9(3) . . . . ?
C14 N2 C10 C9 -77.8(3) . . . . ?
N1 C9 C10 N2 169.2(2) . . . . ?
C10 N2 C11 C12 -176.3(2) . . . . ?
C14 N2 C11 C12 62.3(3) . . . . ?
C13 N3 C12 C11 51.1(3) . . . . ?
N2 C11 C12 N3 -56.9(3) . . . . ?
C12 N3 C13 C14 -52.0(3) . . . . ?
C10 N2 C14 C13 177.4(2) . . . . ?
C11 N2 C14 C13 -62.6(3) . . . . ?
N3 C13 C14 N2 58.2(3) . . . . ?

_refine_diff_density_max         0.669
_refine_diff_density_min         -1.210
_refine_diff_density_rms         0.122



