# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_crystal
_audit_block_doi                 10.5517/ccdc.csd.cc26mvh6
_database_code_depnum_ccdc_archive 'CCDC 2044868'
loop_
_audit_author_name
_audit_author_address
liulehui
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2020-11-17 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
_audit_creation_date             2020-09-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C3 H6 Cl3 N6 Zn, C3 H7 N6'
_chemical_formula_sum            'C6 H13 Cl3 N12 Zn'
_chemical_formula_weight         425.00
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O Zn'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0147 0.0070 '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 0.3292 0.5397 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0135 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -2.8157 0.5450 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.3520(7)
_cell_length_b                   6.7310(5)
_cell_length_c                   12.1408(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.778(7)
_cell_angle_gamma                90
_cell_volume                     748.15(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2628
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.4020
_cell_measurement_theta_min      3.2410
_shelx_estimated_absorpt_T_max   0.451
_shelx_estimated_absorpt_T_min   0.253
_exptl_absorpt_coefficient_mu    4.733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5569
_diffrn_reflns_point_group_measured_fraction_full 0.910
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.601
_diffrn_reflns_theta_min         3.233
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     50.00  79.00   0.50    0.15    --   72.03  77.00   0.00   58
  2  ω     98.00 144.00   0.50    0.15    --   72.03 105.00  47.00   92
  3  ω    107.00 145.00   0.50    0.15    --   72.03 125.00  90.00   76
  4  ω    101.00 145.00   0.50    0.15    --   72.03  77.00   0.00   88
  5  ω      0.00  26.00   0.50    0.15    --   72.03 -19.00  90.00   52
  6  ω     34.00  84.00   0.50    0.15    --   72.03-105.00 -52.00  100
  7  ω     11.00  37.00   0.50    0.15    --   72.03 -38.00 -30.00   52
  8  ω      1.00  42.00   0.50    0.15    --   72.03 -38.00 -60.00   82
  9  ω    -26.00  -1.00   0.50    0.15    --  -75.46  19.00  30.00   50
 10  ω    -43.00 -10.00   0.50    0.15    --  -75.46  38.00  60.00   66
 11  ω    -44.00 -19.00   0.50    0.15    --  -75.46  57.00 -60.00   50
 12  ω    -26.00  -1.00   0.50    0.15    --  -75.46  19.00   0.00   50
 13  ω    -26.00  -1.00   0.50    0.15    --  -75.46  19.00  90.00   50
 14  ω    -26.00  -1.00   0.50    0.15    --  -75.46  19.00  60.00   50
 15  ω    -26.00  -1.00   0.50    0.15    --  -75.46  19.00 150.00   50
 16  ω     34.00  70.00   0.50    0.05    --   -1.72  38.00   0.00   72
 17  ω      4.00  72.00   0.50    0.05    --   -1.72  38.00 -90.00  136
 18  ω    -26.00   0.00   0.50    0.15    --  -75.46  19.00-150.00   52
 19  ω   -104.00 -36.00   0.50    0.15    --  -75.46 105.00  47.00  136
 20  ω   -136.00 -93.00   0.50    0.15    --  -75.46-105.00 -52.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0266899000
_diffrn_orient_matrix_UB_12      -0.1919088000
_diffrn_orient_matrix_UB_13      0.0252078000
_diffrn_orient_matrix_UB_21      0.1197684000
_diffrn_orient_matrix_UB_22      0.0083556000
_diffrn_orient_matrix_UB_23      -0.0442611000
_diffrn_orient_matrix_UB_31      0.0796157000
_diffrn_orient_matrix_UB_32      0.0517329000
_diffrn_orient_matrix_UB_33      0.1005486000
_diffrn_oxdiff_digest_frames     
;
010fbd73b2bee6dd322dc39e8e0527f3b9014485559
;
_diffrn_oxdiff_digest_hkl        
;
01e626c28799c804fdc3a8aedc6ee5130166dd
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_source                   'micro-focus metaljet'
_reflns_Friedel_coverage         0.616
_reflns_Friedel_fraction_full    0.803
_reflns_Friedel_fraction_max     0.711
_reflns_number_gt                2502
_reflns_number_total             2916
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_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       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details 
;
 Flack x determined using 835 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2916
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²+1.3787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1354
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N7(H7)
2.b X=CH2 refined with riding coordinates:
 N10(H10A,H10B), N11(H11A,H11B), N6(H6A,H6B), N4(H4A,H4B), N12(H12A,H12B),
 N5(H5A,H5B)
;
_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 0.91153(11) 0.4349(2) 0.74453(8) 0.0286(3) Uani 1 1 d . . . . .
Cl1 Cl 0.9919(2) 0.2555(3) 0.90470(15) 0.0335(4) Uani 1 1 d . . . . .
Cl3 Cl 0.9827(2) 0.2721(4) 0.60114(16) 0.0379(5) Uani 1 1 d . . . . .
Cl2 Cl 1.0016(2) 0.7455(3) 0.77754(18) 0.0383(5) Uani 1 1 d . . . . .
N3 N 0.6898(6) 0.4838(10) 0.7117(5) 0.0239(14) Uani 1 1 d . . . . .
N1 N 0.4719(7) 0.5605(11) 0.7763(5) 0.0271(14) Uani 1 1 d . . . . .
N2 N 0.4708(7) 0.5520(11) 0.5805(5) 0.0306(16) Uani 1 1 d . . . . .
N10 N 0.3057(7) 0.4843(10) 0.3428(5) 0.0312(16) Uani 1 1 d . . . . .
H10A H 0.349569 0.496975 0.411971 0.037 Uiso 1 1 calc R . . . .
H10B H 0.214269 0.455408 0.326569 0.037 Uiso 1 1 calc R . . . .
N9 N 0.5187(7) 0.5532(11) 0.2852(5) 0.0288(14) Uani 1 1 d . . . . .
N8 N 0.5201(7) 0.5502(12) 0.0878(5) 0.0297(15) Uani 1 1 d . . . . .
N7 N 0.3054(7) 0.4859(11) 0.1524(5) 0.0292(16) Uani 1 1 d . . . . .
H7 H 0.214635 0.453224 0.137858 0.035 Uiso 1 1 calc R . . . .
N11 N 0.3037(8) 0.5090(13) -0.0367(5) 0.042(2) Uani 1 1 d . . . . .
H11A H 0.347072 0.527617 -0.091828 0.050 Uiso 1 1 calc R . . . .
H11B H 0.211321 0.486161 -0.049566 0.050 Uiso 1 1 calc R . . . .
N6 N 0.6815(7) 0.4901(11) 0.9011(5) 0.0328(17) Uani 1 1 d . . . . .
H6A H 0.635249 0.510081 0.954439 0.039 Uiso 1 1 calc R . . . .
H6B H 0.772284 0.457424 0.916633 0.039 Uiso 1 1 calc R . . . .
N4 N 0.6831(7) 0.5094(13) 0.5219(5) 0.040(2) Uani 1 1 d . . . . .
H4A H 0.637187 0.532284 0.454208 0.048 Uiso 1 1 calc R . . . .
H4B H 0.775181 0.484253 0.535199 0.048 Uiso 1 1 calc R . . . .
C2 C 0.6133(8) 0.5094(11) 0.7955(6) 0.0238(15) Uani 1 1 d . . . . .
N12 N 0.7271(7) 0.6028(13) 0.2201(6) 0.0391(18) Uani 1 1 d . . . . .
H12A H 0.773844 0.615101 0.166419 0.047 Uiso 1 1 calc R . . . .
H12B H 0.772677 0.614234 0.288922 0.047 Uiso 1 1 calc R . . . .
C3 C 0.6118(8) 0.5127(12) 0.6058(6) 0.0252(16) Uani 1 1 d . . . . .
C5 C 0.3787(8) 0.5090(12) 0.2619(6) 0.0238(15) Uani 1 1 d . . . . .
N5 N 0.2650(7) 0.6211(14) 0.6459(6) 0.0414(19) Uani 1 1 d . . . . .
H5A H 0.219593 0.639866 0.699914 0.050 Uiso 1 1 calc R . . . .
H5B H 0.219116 0.631994 0.577226 0.050 Uiso 1 1 calc R . . . .
C6 C 0.3783(8) 0.5153(12) 0.0668(6) 0.0255(16) Uani 1 1 d . . . . .
C4 C 0.5871(8) 0.5669(12) 0.1973(6) 0.0268(16) Uani 1 1 d . . . . .
C1 C 0.4046(8) 0.5759(12) 0.6685(6) 0.0264(15) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0219(5) 0.0371(6) 0.0256(5) -0.0004(5) 0.0023(4) 0.0004(6)
Cl1 0.0255(8) 0.0422(11) 0.0313(9) 0.0069(9) 0.0021(7) 0.0013(8)
Cl3 0.0291(10) 0.0530(13) 0.0302(9) -0.0059(10) 0.0027(7) 0.0073(10)
Cl2 0.0280(9) 0.0357(11) 0.0509(12) -0.0052(10) 0.0075(8) -0.0035(9)
N3 0.017(3) 0.037(4) 0.016(3) 0.000(3) 0.002(2) 0.001(3)
N1 0.023(3) 0.038(4) 0.019(3) 0.002(3) 0.003(2) -0.001(3)
N2 0.022(3) 0.048(5) 0.020(3) -0.001(3) 0.002(2) 0.004(3)
N10 0.025(3) 0.044(5) 0.025(3) 0.002(3) 0.006(3) -0.002(3)
N9 0.026(3) 0.038(4) 0.022(3) -0.001(3) 0.005(2) 0.001(3)
N8 0.021(3) 0.047(4) 0.019(3) 0.000(3) 0.002(2) -0.001(3)
N7 0.017(3) 0.044(4) 0.025(3) -0.002(3) 0.001(2) -0.001(3)
N11 0.024(3) 0.077(6) 0.021(3) -0.001(3) -0.002(3) -0.006(3)
N6 0.024(3) 0.056(5) 0.017(3) 0.001(3) 0.003(2) 0.006(3)
N4 0.022(3) 0.081(6) 0.015(3) 0.005(3) 0.001(2) 0.014(3)
C2 0.022(3) 0.028(4) 0.022(3) 0.001(3) 0.004(3) 0.004(3)
N12 0.022(3) 0.064(5) 0.030(4) 0.006(4) 0.003(3) -0.004(4)
C3 0.021(3) 0.034(4) 0.020(4) 0.000(3) 0.003(3) 0.000(3)
C5 0.021(3) 0.030(4) 0.019(3) -0.002(3) 0.001(3) 0.001(3)
N5 0.023(3) 0.075(6) 0.025(3) 0.003(4) 0.002(3) 0.005(4)
C6 0.023(4) 0.033(4) 0.019(3) -0.002(3) 0.001(3) 0.000(3)
C4 0.024(4) 0.035(4) 0.020(3) 0.003(3) 0.000(3) -0.003(3)
C1 0.021(3) 0.032(4) 0.026(4) -0.001(3) 0.004(3) 0.001(3)

_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 Cl1 2.282(2) . ?
Zn1 Cl3 2.269(2) . ?
Zn1 Cl2 2.260(3) . ?
Zn1 N3 2.057(6) . ?
N3 C2 1.369(9) . ?
N3 C3 1.356(9) . ?
N1 C2 1.340(9) . ?
N1 C1 1.336(10) . ?
N2 C3 1.319(9) . ?
N2 C1 1.349(9) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N10 C5 1.316(9) . ?
N9 C5 1.316(9) . ?
N9 C4 1.355(9) . ?
N8 C6 1.319(9) . ?
N8 C4 1.353(9) . ?
N7 H7 0.8600 . ?
N7 C5 1.374(9) . ?
N7 C6 1.368(9) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N11 C6 1.307(9) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N6 C2 1.316(9) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C3 1.327(9) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N12 C4 1.305(10) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N5 C1 1.313(10) . ?

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
Cl3 Zn1 Cl1 107.53(10) . . ?
Cl2 Zn1 Cl1 107.01(9) . . ?
Cl2 Zn1 Cl3 115.20(10) . . ?
N3 Zn1 Cl1 113.18(18) . . ?
N3 Zn1 Cl3 111.75(18) . . ?
N3 Zn1 Cl2 102.2(2) . . ?
C2 N3 Zn1 122.4(5) . . ?
C3 N3 Zn1 122.2(5) . . ?
C3 N3 C2 115.2(6) . . ?
C1 N1 C2 116.2(6) . . ?
C3 N2 C1 116.0(6) . . ?
H10A N10 H10B 120.0 . . ?
C5 N10 H10A 120.0 . . ?
C5 N10 H10B 120.0 . . ?
C5 N9 C4 117.1(6) . . ?
C6 N8 C4 116.8(6) . . ?
C5 N7 H7 120.3 . . ?
C6 N7 H7 120.3 . . ?
C6 N7 C5 119.4(6) . . ?
H11A N11 H11B 120.0 . . ?
C6 N11 H11A 120.0 . . ?
C6 N11 H11B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C2 N6 H6A 120.0 . . ?
C2 N6 H6B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C3 N4 H4A 120.0 . . ?
C3 N4 H4B 120.0 . . ?
N1 C2 N3 123.3(6) . . ?
N6 C2 N3 119.2(6) . . ?
N6 C2 N1 117.4(7) . . ?
H12A N12 H12B 120.0 . . ?
C4 N12 H12A 120.0 . . ?
C4 N12 H12B 120.0 . . ?
N2 C3 N3 124.7(7) . . ?
N2 C3 N4 117.3(7) . . ?
N4 C3 N3 117.9(7) . . ?
N10 C5 N9 120.8(7) . . ?
N10 C5 N7 118.4(7) . . ?
N9 C5 N7 120.7(7) . . ?
H5A N5 H5B 120.0 . . ?
C1 N5 H5A 120.0 . . ?
C1 N5 H5B 120.0 . . ?
N8 C6 N7 121.0(6) . . ?
N11 C6 N8 120.6(7) . . ?
N11 C6 N7 118.3(7) . . ?
N8 C4 N9 124.7(7) . . ?
N12 C4 N9 117.4(7) . . ?
N12 C4 N8 117.9(7) . . ?
N1 C1 N2 124.5(7) . . ?
N5 C1 N1 118.1(7) . . ?
N5 C1 N2 117.4(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.775
_oxdiff_exptl_absorpt_empirical_full_min 0.415
