# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2023896'
_audit_update_record             
;
2020-08-18 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 Cl2 N5 O2 Zn'
_chemical_formula_weight         561.75

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   11.749(3)
_cell_length_b                   8.961(2)
_cell_length_c                   25.585(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.49(3)
_cell_angle_gamma                90.00
_cell_volume                     2639.7(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2963
_cell_measurement_theta_min      0.267
_cell_measurement_theta_max      0.322

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    1.164
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.2307
_exptl_absorpt_correction_T_max  0.3973
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'phi and omega scans'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6870
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2331
_reflns_number_gt                1967
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0456P)²+0.9705P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2331
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C13 C 0.5695(4) 1.0093(5) 0.92608(19) 0.0913(14) Uani 1 1 d . . .
H13A H 0.6381 1.0152 0.9536 0.137 Uiso 1 1 calc R . .
H13B H 0.5184 1.0905 0.9299 0.137 Uiso 1 1 calc R . .
H13C H 0.5907 1.0151 0.8918 0.137 Uiso 1 1 calc R . .
Zn1 Zn 0.5000 0.34349(4) 0.7500 0.03504(17) Uani 1 2 d S . .
Cl2 Cl 0.36511(6) 0.21870(8) 0.69342(3) 0.0467(2) Uani 1 1 d . . .
O1 O 0.2323(2) 0.0429(2) 0.95495(8) 0.0566(6) Uani 1 1 d . . .
N5 N 0.39590(19) 0.4121(2) 0.81353(9) 0.0351(5) Uani 1 1 d . . .
N6 N 0.5000 0.5709(3) 0.7500 0.0361(7) Uani 1 2 d S . .
C1 C 0.1759(3) -0.0933(4) 0.93829(15) 0.0705(11) Uani 1 1 d . . .
H1A H 0.1118 -0.0749 0.9093 0.106 Uiso 1 1 calc R . .
H1B H 0.1478 -0.1373 0.9675 0.106 Uiso 1 1 calc R . .
H1C H 0.2298 -0.1601 0.9268 0.106 Uiso 1 1 calc R . .
C11 C 0.5000 0.8758(5) 0.7500 0.0643(14) Uani 1 2 d S . .
H11 H 0.5000 0.9796 0.7500 0.077 Uiso 1 2 calc SR . .
C10 C 0.4458(3) 0.7991(3) 0.78417(14) 0.0560(9) Uani 1 1 d . . .
H10 H 0.4082 0.8499 0.8075 0.067 Uiso 1 1 calc R . .
C2 C 0.2689(2) 0.1282(3) 0.91794(12) 0.0416(7) Uani 1 1 d . . .
C6 C 0.3052(3) 0.1845(3) 0.83158(11) 0.0399(7) Uani 1 1 d . . .
H6 H 0.3030 0.1564 0.7964 0.048 Uiso 1 1 calc R . .
C7 C 0.2612(2) 0.0890(3) 0.86532(11) 0.0429(7) Uani 1 1 d . . .
H7 H 0.2269 -0.0008 0.8525 0.052 Uiso 1 1 calc R . .
C3 C 0.3184(3) 0.2625(3) 0.93642(12) 0.0466(8) Uani 1 1 d . . .
H3 H 0.3243 0.2884 0.9720 0.056 Uiso 1 1 calc R . .
C4 C 0.3590(3) 0.3575(3) 0.90264(12) 0.0432(7) Uani 1 1 d . . .
H4 H 0.3917 0.4482 0.9154 0.052 Uiso 1 1 calc R . .
C5 C 0.3518(2) 0.3200(3) 0.84947(11) 0.0353(6) Uani 1 1 d . . .
C9 C 0.4476(3) 0.6450(3) 0.78349(12) 0.0410(7) Uani 1 1 d . . .
C8 C 0.3942(2) 0.5532(3) 0.81944(11) 0.0402(7) Uani 1 1 d . . .
C12 C 0.5114(4) 0.8702(6) 0.93048(17) 0.0776(12) Uani 1 1 d . . .
N7 N 0.4658(4) 0.7623(5) 0.93411(18) 0.1096(14) 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
C13 C12 1.436(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
Zn1 N6 2.038(3) . ?
Zn1 Cl2 2.2235(9) . ?
Zn1 Cl2 2.2235(9) 2_656 ?
Zn1 N5 2.304(2) . ?
Zn1 N5 2.304(2) 2_656 ?
O1 C2 1.352(3) . ?
O1 C1 1.413(4) . ?
N5 C8 1.274(3) . ?
N5 C5 1.408(3) . ?
N6 C9 1.328(3) . ?
N6 C9 1.328(3) 2_656 ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C11 C10 1.365(4) 2_656 ?
C11 C10 1.365(4) . ?
C11 H11 0.9300 . ?
C10 C9 1.382(4) . ?
C10 H10 0.9300 . ?
C2 C7 1.377(4) . ?
C2 C3 1.378(4) . ?
C6 C5 1.373(4) . ?
C6 C7 1.386(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C3 C4 1.365(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9300 . ?
C9 C8 1.465(4) . ?
C12 N7 1.118(6) . ?

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
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N6 Zn1 Cl2 120.19(2) . . ?
N6 Zn1 Cl2 120.19(2) . 2_656 ?
Cl2 Zn1 Cl2 119.61(5) . 2_656 ?
N6 Zn1 N5 74.53(6) . . ?
Cl2 Zn1 N5 100.59(6) . . ?
Cl2 Zn1 N5 94.84(6) 2_656 . ?
N6 Zn1 N5 74.53(6) . 2_656 ?
Cl2 Zn1 N5 94.85(6) . 2_656 ?
Cl2 Zn1 N5 100.59(6) 2_656 2_656 ?
N5 Zn1 N5 149.07(11) . 2_656 ?
C2 O1 C1 118.2(2) . . ?
C8 N5 C5 119.1(2) . . ?
C8 N5 Zn1 111.81(19) . . ?
C5 N5 Zn1 128.35(16) . . ?
C9 N6 C9 120.0(3) . 2_656 ?
C9 N6 Zn1 119.98(16) . . ?
C9 N6 Zn1 119.98(16) 2_656 . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C10 C11 C10 119.6(4) 2_656 . ?
C10 C11 H11 120.2 2_656 . ?
C10 C11 H11 120.2 . . ?
C11 C10 C9 119.0(3) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
O1 C2 C7 124.9(3) . . ?
O1 C2 C3 115.2(3) . . ?
C7 C2 C3 119.9(3) . . ?
C5 C6 C7 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C6 119.4(3) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 118.9(3) . . ?
C6 C5 N5 118.3(2) . . ?
C4 C5 N5 122.7(2) . . ?
N6 C9 C10 121.2(3) . . ?
N6 C9 C8 115.9(2) . . ?
C10 C9 C8 122.9(3) . . ?
N5 C8 C9 117.6(3) . . ?
N7 C12 C13 179.6(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
N6 Zn1 N5 C8 -3.25(18) . . . . ?
Cl2 Zn1 N5 C8 -121.88(19) . . . . ?
Cl2 Zn1 N5 C8 116.77(19) 2_656 . . . ?
N5 Zn1 N5 C8 -3.24(18) 2_656 . . . ?
N6 Zn1 N5 C5 -173.5(2) . . . . ?
Cl2 Zn1 N5 C5 67.9(2) . . . . ?
Cl2 Zn1 N5 C5 -53.5(2) 2_656 . . . ?
N5 Zn1 N5 C5 -173.5(2) 2_656 . . . ?
Cl2 Zn1 N6 C9 94.47(15) . . . . ?
Cl2 Zn1 N6 C9 -85.53(15) 2_656 . . . ?
N5 Zn1 N6 C9 1.05(15) . . . . ?
N5 Zn1 N6 C9 -178.94(15) 2_656 . . . ?
Cl2 Zn1 N6 C9 -85.53(15) . . . 2_656 ?
Cl2 Zn1 N6 C9 94.48(15) 2_656 . . 2_656 ?
N5 Zn1 N6 C9 -178.94(15) . . . 2_656 ?
N5 Zn1 N6 C9 1.06(15) 2_656 . . 2_656 ?
C10 C11 C10 C9 0.3(2) 2_656 . . . ?
C1 O1 C2 C7 -3.8(5) . . . . ?
C1 O1 C2 C3 177.2(3) . . . . ?
O1 C2 C7 C6 -178.1(3) . . . . ?
C3 C2 C7 C6 0.9(5) . . . . ?
C5 C6 C7 C2 -2.7(4) . . . . ?
O1 C2 C3 C4 179.7(3) . . . . ?
C7 C2 C3 C4 0.7(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C7 C6 C5 C4 2.8(4) . . . . ?
C7 C6 C5 N5 179.6(2) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C3 C4 C5 N5 -177.8(3) . . . . ?
C8 N5 C5 C6 150.9(3) . . . . ?
Zn1 N5 C5 C6 -39.5(3) . . . . ?
C8 N5 C5 C4 -32.4(4) . . . . ?
Zn1 N5 C5 C4 137.2(2) . . . . ?
C9 N6 C9 C10 0.3(2) 2_656 . . . ?
Zn1 N6 C9 C10 -179.7(2) . . . . ?
C9 N6 C9 C8 -179.0(3) 2_656 . . . ?
Zn1 N6 C9 C8 1.0(3) . . . . ?
C11 C10 C9 N6 -0.6(4) . . . . ?
C11 C10 C9 C8 178.6(2) . . . . ?
C5 N5 C8 C9 176.1(2) . . . . ?
Zn1 N5 C8 C9 4.8(3) . . . . ?
N6 C9 C8 N5 -4.2(4) . . . . ?
C10 C9 C8 N5 176.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.059
