# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_esk-915-2
_database_code_depnum_ccdc_archive 'CCDC 2496541'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2025-10-20 deposited with the CCDC.	2025-12-14 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 Cl2 N2 O Zn'
_chemical_formula_sum            'C14 H22 Cl2 N2 O Zn'
_chemical_formula_weight         370.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   13.779(2)
_cell_length_b                   7.4635(12)
_cell_length_c                   17.382(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.328(6)
_cell_angle_gamma                90
_cell_volume                     1641.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    450
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      24.32

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.819
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_detector_type            'Bruker PHOTON II CPAD area detector'
_diffrn_measurement_method       'ο scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15020
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.419
_diffrn_reflns_theta_max         29.214
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4406
_reflns_number_gt                2839
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0478P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4406
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_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 0.11961(3) 0.25330(5) 0.66482(2) 0.02025(11) Uani 1 1 d . . . . .
O1 O 0.44986(19) 0.6889(3) 0.73598(14) 0.0321(6) Uani 1 1 d . . . . .
N1 N 0.2182(2) 0.2318(3) 0.59956(15) 0.0199(5) Uani 1 1 d . . . . .
N2 N 0.1470(2) 0.5145(3) 0.70777(15) 0.0193(5) Uani 1 1 d . . . . .
C1 C 0.2569(3) 0.0447(4) 0.6050(2) 0.0283(7) Uani 1 1 d . . . . .
H1A H 0.304613 0.035199 0.575741 0.042 Uiso 1 1 calc R U . . .
H1B H 0.196665 -0.036175 0.578778 0.042 Uiso 1 1 calc R U . . .
H1C H 0.294847 0.011537 0.663904 0.042 Uiso 1 1 calc R U . . .
C2 C 0.1593(3) 0.2761(4) 0.50985(19) 0.0245(7) Uani 1 1 d . . . . .
H2A H 0.207508 0.271531 0.480866 0.037 Uiso 1 1 calc R U . . .
H2B H 0.129437 0.396779 0.504887 0.037 Uiso 1 1 calc R U . . .
H2C H 0.102139 0.189237 0.484469 0.037 Uiso 1 1 calc R U . . .
C3 C 0.1318(3) 0.5279(4) 0.78760(19) 0.0269(7) Uani 1 1 d . . . . .
H3A H 0.142833 0.652164 0.807476 0.040 Uiso 1 1 calc R U . . .
H3B H 0.182682 0.449932 0.829728 0.040 Uiso 1 1 calc R U . . .
H3C H 0.059772 0.490625 0.778227 0.040 Uiso 1 1 calc R U . . .
C4 C 0.0687(2) 0.6386(4) 0.64729(19) 0.0228(7) Uani 1 1 d . . . . .
H4A H 0.083618 0.761720 0.668218 0.034 Uiso 1 1 calc R U . . .
H4B H -0.002788 0.605132 0.641203 0.034 Uiso 1 1 calc R U . . .
H4C H 0.073759 0.630277 0.592738 0.034 Uiso 1 1 calc R U . . .
C5 C 0.3119(2) 0.3493(4) 0.63728(18) 0.0203(6) Uani 1 1 d . . . . .
H5A H 0.352199 0.346370 0.601114 0.024 Uiso 1 1 calc R U . . .
H5B H 0.357981 0.298894 0.692370 0.024 Uiso 1 1 calc R U . . .
C6 C 0.2564(2) 0.5747(4) 0.72383(18) 0.0208(6) Uani 1 1 d . . . . .
H6A H 0.306551 0.509062 0.772984 0.025 Uiso 1 1 calc R U . . .
H6B H 0.262605 0.703746 0.738138 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2883(2) 0.5462(4) 0.64995(18) 0.0188(6) Uani 1 1 d . . . . .
H7A H 0.231196 0.592311 0.597544 0.023 Uiso 1 1 calc R U . . .
C8 C 0.3909(2) 0.6461(4) 0.66544(19) 0.0214(6) Uani 1 1 d . . . . .
C9 C 0.4188(3) 0.6823(4) 0.59198(19) 0.0214(6) Uani 1 1 d . . . . .
C10 C 0.5248(3) 0.7189(4) 0.6073(2) 0.0283(8) Uani 1 1 d . . . . .
H10A H 0.576841 0.718016 0.663087 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5534(3) 0.7561(5) 0.5417(2) 0.0346(8) Uani 1 1 d . . . . .
H11A H 0.625264 0.780774 0.552488 0.042 Uiso 1 1 calc R U . . .
C12 C 0.4795(3) 0.7581(4) 0.4608(2) 0.0304(7) Uani 1 1 d . . . . .
H12A H 0.500038 0.786375 0.416124 0.036 Uiso 1 1 calc R U . . .
C13 C 0.3751(3) 0.7191(4) 0.4443(2) 0.0292(8) Uani 1 1 d . . . . .
H13A H 0.324144 0.717690 0.388195 0.035 Uiso 1 1 calc R U . . .
C14 C 0.3447(3) 0.6818(4) 0.5099(2) 0.0252(7) Uani 1 1 d . . . . .
H14A H 0.272757 0.655982 0.498515 0.030 Uiso 1 1 calc R U . . .
Cl1 Cl 0.18300(7) 0.07572(11) 0.77675(5) 0.0298(2) Uani 1 1 d . . . . .
Cl2 Cl -0.04581(6) 0.22101(11) 0.57086(5) 0.02629(19) 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 2.068(3) . ?
Zn1 N1 2.092(2) . ?
Zn1 Cl1 2.2269(9) . ?
Zn1 Cl2 2.2299(9) . ?
O1 C8 1.215(4) . ?
N1 C5 1.482(4) . ?
N1 C2 1.482(4) . ?
N1 C1 1.484(4) . ?
N2 C3 1.487(4) . ?
N2 C6 1.489(4) . ?
N2 C4 1.493(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C7 1.539(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.528(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.525(4) . ?
C7 H7A 1.0000 . ?
C8 C9 1.497(4) . ?
C9 C14 1.387(4) . ?
C9 C10 1.404(4) . ?
C10 C11 1.375(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.371(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.382(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.390(4) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N1 101.72(9) . . ?
N2 Zn1 Cl1 107.05(7) . . ?
N1 Zn1 Cl1 108.29(7) . . ?
N2 Zn1 Cl2 110.72(7) . . ?
N1 Zn1 Cl2 106.82(7) . . ?
Cl1 Zn1 Cl2 120.60(3) . . ?
C5 N1 C2 110.6(2) . . ?
C5 N1 C1 107.5(2) . . ?
C2 N1 C1 108.0(2) . . ?
C5 N1 Zn1 110.72(17) . . ?
C2 N1 Zn1 110.56(19) . . ?
C1 N1 Zn1 109.39(18) . . ?
C3 N2 C6 108.1(2) . . ?
C3 N2 C4 106.6(2) . . ?
C6 N2 C4 109.9(2) . . ?
C3 N2 Zn1 109.13(19) . . ?
C6 N2 Zn1 112.26(18) . . ?
C4 N2 Zn1 110.66(19) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C7 115.6(2) . . ?
N1 C5 H5A 108.4 . . ?
C7 C5 H5A 108.4 . . ?
N1 C5 H5B 108.4 . . ?
C7 C5 H5B 108.4 . . ?
H5A C5 H5B 107.4 . . ?
N2 C6 C7 114.0(2) . . ?
N2 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
N2 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C6 109.8(2) . . ?
C8 C7 C5 105.0(2) . . ?
C6 C7 C5 113.6(2) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C5 C7 H7A 109.4 . . ?
O1 C8 C9 121.2(3) . . ?
O1 C8 C7 120.6(3) . . ?
C9 C8 C7 118.1(3) . . ?
C14 C9 C10 118.9(3) . . ?
C14 C9 C8 122.9(3) . . ?
C10 C9 C8 118.2(3) . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C9 C14 C13 120.3(3) . . ?
C9 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?

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
C2 N1 C5 C7 71.2(3) . . . . ?
C1 N1 C5 C7 -171.1(2) . . . . ?
Zn1 N1 C5 C7 -51.7(3) . . . . ?
C3 N2 C6 C7 172.8(3) . . . . ?
C4 N2 C6 C7 -71.3(3) . . . . ?
Zn1 N2 C6 C7 52.3(3) . . . . ?
N2 C6 C7 C8 168.2(3) . . . . ?
N2 C6 C7 C5 -74.6(3) . . . . ?
N1 C5 C7 C8 -164.7(2) . . . . ?
N1 C5 C7 C6 75.3(3) . . . . ?
C6 C7 C8 O1 20.8(4) . . . . ?
C5 C7 C8 O1 -101.7(3) . . . . ?
C6 C7 C8 C9 -161.9(3) . . . . ?
C5 C7 C8 C9 75.6(3) . . . . ?
O1 C8 C9 C14 -161.9(3) . . . . ?
C7 C8 C9 C14 20.8(5) . . . . ?
O1 C8 C9 C10 17.8(5) . . . . ?
C7 C8 C9 C10 -159.5(3) . . . . ?
C14 C9 C10 C11 0.9(5) . . . . ?
C8 C9 C10 C11 -178.8(3) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C10 C11 C12 C13 -1.2(5) . . . . ?
C11 C12 C13 C14 1.5(5) . . . . ?
C10 C9 C14 C13 -0.7(5) . . . . ?
C8 C9 C14 C13 179.0(3) . . . . ?
C12 C13 C14 C9 -0.5(5) . . . . ?

_refine_diff_density_max         0.757
_refine_diff_density_min         -1.277
_refine_diff_density_rms         0.105



