# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_mo_180508_lhd8_0m
_database_code_depnum_ccdc_archive 'CCDC 2283702'
loop_
_audit_author_name
_audit_author_address
'Li hai-tao'
;Heze University Liaoning  University
China
;
_audit_update_record             
;
2023-11-17 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
_audit_creation_date             2023-11-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl4 Co), C14 H22 N4, 2(H2 O)'
_chemical_formula_sum            'C14 H26 Cl8 Co2 N4 O2'
_chemical_formula_weight         683.85
_chemical_melting_point          ?
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'
Co Co 0.3494 0.9721 '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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8956(5)
_cell_length_b                   14.3091(8)
_cell_length_c                   10.4218(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.766(2)
_cell_angle_gamma                90
_cell_volume                     1325.02(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    298.27
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.575
_shelx_estimated_absorpt_T_min   0.575
_exptl_absorpt_coefficient_mu    2.078
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0974 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.6228.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23877
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         2.420
_diffrn_ambient_temperature      298.27
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2868
_reflns_number_total             3256
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3256
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0267
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0261P)²+0.5482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0658
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All H(H,H) groups
2. Restrained distances
 H1AB-H1AA
 1.39 with sigma of 0.01
 O1-H1AB
 0.89 with sigma of 0.01
 O1-H1AA
 0.89 with sigma of 0.01
 H1BD-H1BC
 1.39 with sigma of 0.01
 O1-H1AA \\sim O1-H1BC
 with sigma of 0.02
 O1-H1AB \\sim O1-H1BD
 with sigma of 0.02
3. Others
 Sof(H1BC)=Sof(H1BD)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C7(H7A,H7B), C6(H6A,H6B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C3(H3), C2(H2A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Co1 Co 0.51065(3) 0.25372(2) 0.16604(2) 0.03473(8) Uani 1 1 d . . . . .
Cl1 Cl 0.65931(5) 0.25703(3) 0.35404(4) 0.04257(11) Uani 1 1 d . . . . .
Cl2 Cl 0.35257(6) 0.13149(4) 0.19208(5) 0.05049(13) Uani 1 1 d . . . . .
Cl3 Cl 0.65610(6) 0.22433(4) -0.00096(5) 0.05165(13) Uani 1 1 d . . . . .
Cl4 Cl 0.39811(6) 0.39505(3) 0.15839(6) 0.05541(14) Uani 1 1 d . . . . .
N1 N 0.63536(15) 0.48822(10) 0.36796(12) 0.0336(3) Uani 1 1 d . . . . .
H1A H 0.599149 0.433725 0.339239 0.040 Uiso 1 1 calc R U . . .
H1B H 0.597019 0.532803 0.316608 0.040 Uiso 1 1 calc R U . . .
N2 N 0.93660(17) 0.38085(10) 0.00598(15) 0.0389(3) Uani 1 1 d . . . . .
O1 O 0.5360(2) 0.64545(14) 0.2364(2) 0.0720(5) Uani 1 1 d D . . . .
C7 C 0.58447(18) 0.50396(14) 0.49976(15) 0.0382(4) Uani 1 1 d . . . . .
H7A H 0.615620 0.565576 0.529341 0.046 Uiso 1 1 calc R U . . .
H7B H 0.630379 0.458053 0.557852 0.046 Uiso 1 1 calc R U . . .
C5 C 0.84927(17) 0.45260(11) 0.23201(15) 0.0310(3) Uani 1 1 d . . . . .
C4 C 0.9717(2) 0.39272(13) 0.22934(18) 0.0403(4) Uani 1 1 d . . . . .
H4 H 1.025294 0.377012 0.305107 0.048 Uiso 1 1 calc R U . . .
C1 C 0.8205(2) 0.43913(13) 0.00420(16) 0.0396(4) Uani 1 1 d . . . . .
H1 H 0.770225 0.454377 -0.073312 0.047 Uiso 1 1 calc R U . . .
C3 C 0.77447(19) 0.47694(12) 0.11711(16) 0.0361(4) Uani 1 1 d . . . . .
H3 H 0.693968 0.518436 0.116377 0.043 Uiso 1 1 calc R U . . .
C6 C 0.80129(19) 0.48780(14) 0.35990(16) 0.0392(4) Uani 1 1 d . . . . .
H6A H 0.845232 0.448470 0.427613 0.047 Uiso 1 1 calc R U . . .
H6B H 0.839255 0.550747 0.373504 0.047 Uiso 1 1 calc R U . . .
C2 C 1.0133(2) 0.35679(13) 0.1142(2) 0.0438(4) Uani 1 1 d . . . . .
H2A H 1.094474 0.315951 0.111533 0.053 Uiso 1 1 calc R U . . .
H2 H 0.965(3) 0.3556(17) -0.068(2) 0.060(7) Uiso 1 1 d . . . . .
H1AA H 0.602(3) 0.682(3) 0.199(4) 0.090 Uiso 0.65(4) 1 d D U P A 1
H1AB H 0.450(2) 0.658(3) 0.194(4) 0.090 Uiso 0.65(4) 1 d D U P A 1
H1BC H 0.498(9) 0.599(6) 0.187(9) 0.14(5) Uiso 0.35(4) 1 d D . P A 2
H1BD H 0.456(7) 0.662(6) 0.279(9) 0.11(4) Uiso 0.35(4) 1 d D . P A 2


_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
Co1 Cl1 2.3108(5) . ?
Co1 Cl2 2.2687(5) . ?
Co1 Cl3 2.2577(5) . ?
Co1 Cl4 2.2562(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C7 1.4841(19) . ?
N1 C6 1.482(2) . ?
N2 C1 1.327(2) . ?
N2 C2 1.335(3) . ?
N2 H2 0.90(2) . ?
O1 H1AA 0.890(10) . ?
O1 H1AB 0.885(10) . ?
O1 H1BC 0.90(2) . ?
O1 H1BD 0.89(2) . ?
C7 C7 1.507(3) 3_666 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 C4 1.387(2) . ?
C5 C3 1.386(2) . ?
C5 C6 1.506(2) . ?
C4 H4 0.9300 . ?
C4 C2 1.373(3) . ?
C1 H1 0.9300 . ?
C1 C3 1.375(2) . ?
C3 H3 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C2 H2A 0.9300 . ?

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
Cl2 Co1 Cl1 104.301(18) . . ?
Cl3 Co1 Cl1 109.37(2) . . ?
Cl3 Co1 Cl2 109.28(2) . . ?
Cl4 Co1 Cl1 104.26(2) . . ?
Cl4 Co1 Cl2 114.75(2) . . ?
Cl4 Co1 Cl3 114.18(2) . . ?
H1A N1 H1B 107.7 . . ?
C7 N1 H1A 108.8 . . ?
C7 N1 H1B 108.8 . . ?
C6 N1 H1A 108.8 . . ?
C6 N1 H1B 108.8 . . ?
C6 N1 C7 113.71(13) . . ?
C1 N2 C2 122.69(15) . . ?
C1 N2 H2 119.6(15) . . ?
C2 N2 H2 117.7(15) . . ?
H1AA O1 H1AB 103.2(15) . . ?
H1BC O1 H1BD 102(3) . . ?
N1 C7 C7 109.90(17) . 3_666 ?
N1 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
C7 C7 H7A 109.7 3_666 . ?
C7 C7 H7B 109.7 3_666 . ?
H7A C7 H7B 108.2 . . ?
C4 C5 C6 118.74(15) . . ?
C3 C5 C4 118.85(15) . . ?
C3 C5 C6 122.41(15) . . ?
C5 C4 H4 120.2 . . ?
C2 C4 C5 119.61(17) . . ?
C2 C4 H4 120.2 . . ?
N2 C1 H1 120.0 . . ?
N2 C1 C3 119.92(16) . . ?
C3 C1 H1 120.0 . . ?
C5 C3 H3 120.3 . . ?
C1 C3 C5 119.35(16) . . ?
C1 C3 H3 120.3 . . ?
N1 C6 C5 112.15(13) . . ?
N1 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C2 C4 119.56(16) . . ?
N2 C2 H2A 120.2 . . ?
C4 C2 H2A 120.2 . . ?

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
N2 C1 C3 C5 -0.8(3) . . . . ?
C7 N1 C6 C5 168.37(15) . . . . ?
C5 C4 C2 N2 0.8(3) . . . . ?
C4 C5 C3 C1 1.9(2) . . . . ?
C4 C5 C6 N1 -138.40(16) . . . . ?
C1 N2 C2 C4 0.3(3) . . . . ?
C3 C5 C4 C2 -1.9(3) . . . . ?
C3 C5 C6 N1 40.8(2) . . . . ?
C6 N1 C7 C7 -175.77(19) . . . 3_666 ?
C6 C5 C4 C2 177.30(16) . . . . ?
C6 C5 C3 C1 -177.28(16) . . . . ?
C2 N2 C1 C3 -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 2283703'
loop_
_audit_author_name
_audit_author_address
'Li hai-tao'
;Heze University Liaoning  University
China
;
_audit_update_record             
;
2023-11-17 deposited with the CCDC.	2023-12-06 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         '2(Cl4 Zn), C14 H22 N4, 2(H2 O)'
_chemical_formula_sum            'C14 H26 Cl8 N4 O2 Zn2'
_chemical_formula_weight         696.73

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.9266(8)
_cell_length_b                   14.2573(12)
_cell_length_c                   10.4071(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.659(2)
_cell_angle_gamma                90
_cell_volume                     1323.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8553
_cell_measurement_theta_min      3.078
_cell_measurement_theta_max      28.319

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_F_000             700
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.89
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    2.640
_shelx_estimated_absorpt_T_min   0.628
_shelx_estimated_absorpt_T_max   0.748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4382
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7723
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.078
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             2250
_reflns_number_gt                2077
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0624P)²+5.4708P] 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         2250
_refine_ls_number_parameters     151
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.055
_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 0.49026(6) 0.75314(3) 0.83619(5) 0.0304(2) Uani 1 1 d . . . . .
Cl1 Cl 0.34053(14) 0.75555(8) 0.64751(12) 0.0359(3) Uani 1 1 d . . . . .
Cl2 Cl 0.64558(16) 0.62995(10) 0.80932(13) 0.0470(4) Uani 1 1 d . . . . .
Cl3 Cl 0.34488(17) 0.72557(11) 1.00241(13) 0.0491(4) Uani 1 1 d . . . . .
Cl4 Cl 0.60404(16) 0.89377(9) 0.83978(15) 0.0514(4) Uani 1 1 d . . . . .
N1 N 0.8655(4) 0.5125(3) 0.1319(4) 0.0318(9) Uani 1 1 d . . . . .
H1A H 0.904687 0.468562 0.184046 0.038 Uiso 1 1 calc DR U . . .
H1B H 0.900601 0.567750 0.159582 0.038 Uiso 1 1 calc R U . . .
N2 N 0.5635(5) 0.6187(3) 0.4953(4) 0.0385(10) Uani 1 1 d . . . . .
H2 H 0.536672 0.642054 0.566884 0.046 Uiso 1 1 calc R U . . .
O1 O 0.9646(5) 0.3555(3) 0.2624(5) 0.0722(14) Uani 1 1 d DG . . . .
H1D H 0.933657 0.316085 0.316380 0.108 Uiso 1 1 d DG U . . .
C2 C 0.6795(6) 0.5603(4) 0.4962(5) 0.0363(11) Uani 1 1 d . . . . .
H2A H 0.728948 0.544574 0.573855 0.044 Uiso 1 1 calc R U . . .
C7 C 0.9160(5) 0.4960(4) 0.0009(4) 0.0372(11) Uani 1 1 d . . . . .
H7A H 0.869880 0.541569 -0.057776 0.045 Uiso 1 1 calc R U . . .
H7B H 0.885032 0.433914 -0.027813 0.045 Uiso 1 1 calc R U . . .
C5 C 0.6521(5) 0.5472(3) 0.2693(4) 0.0300(10) Uani 1 1 d . . . . .
C4 C 0.7268(6) 0.5231(3) 0.3837(4) 0.0346(10) Uani 1 1 d . . . . .
H4 H 0.808036 0.482219 0.384415 0.041 Uiso 1 1 calc R U . . .
C3 C 0.5287(5) 0.6073(4) 0.2714(5) 0.0374(11) Uani 1 1 d . . . . .
H3 H 0.475607 0.623220 0.195582 0.045 Uiso 1 1 calc R U . . .
C6 C 0.7011(5) 0.5119(4) 0.1407(5) 0.0379(11) Uani 1 1 d . . . . .
H6A H 0.664400 0.448431 0.127374 0.045 Uiso 1 1 calc R U . . .
H6B H 0.656487 0.550918 0.072826 0.045 Uiso 1 1 calc R U . . .
C1 C 0.4873(6) 0.6424(4) 0.3868(6) 0.0445(13) Uani 1 1 d . . . . .
H1 H 0.405755 0.682844 0.389635 0.053 Uiso 1 1 calc R U . . .
H1C H 1.07(3) 0.366(17) 0.35(2) 0.067 Uiso 0.29(3) 1 d . U P A 1
H1F H 1.052(2) 0.380(3) 0.290(5) 0.067 Uiso 0.26(3) 1 d D U P B 2
H1E H 1.0594(18) 0.338(4) 0.277(10) 0.067 Uiso 0.44(3) 1 d D U P C 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 Cl3 2.2449(15) . ?
Zn1 Cl4 2.2471(14) . ?
Zn1 Cl2 2.2631(13) . ?
Zn1 Cl1 2.3237(13) . ?
N1 C6 1.475(6) . ?
N1 C7 1.475(6) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N2 C2 1.329(7) . ?
N2 C1 1.334(7) . ?
N2 H2 0.8600 . ?
O1 H1D 0.8501 . ?
O1 H1C 1.3(2) . ?
O1 H1F 0.8900 . ?
O1 H1E 0.8900 . ?
C2 C4 1.370(7) . ?
C2 H2A 0.9300 . ?
C7 C7 1.505(10) 3_765 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 C4 1.381(7) . ?
C5 C3 1.396(7) . ?
C5 C6 1.513(6) . ?
C4 H4 0.9300 . ?
C3 C1 1.367(8) . ?
C3 H3 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C1 H1 0.9300 . ?

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 Cl4 114.86(6) . . ?
Cl3 Zn1 Cl2 109.80(6) . . ?
Cl4 Zn1 Cl2 114.55(6) . . ?
Cl3 Zn1 Cl1 108.87(6) . . ?
Cl4 Zn1 Cl1 104.04(5) . . ?
Cl2 Zn1 Cl1 103.81(5) . . ?
C6 N1 C7 113.8(4) . . ?
C6 N1 H1A 108.8 . . ?
C7 N1 H1A 108.8 . . ?
C6 N1 H1B 108.8 . . ?
C7 N1 H1B 108.8 . . ?
H1A N1 H1B 107.7 . . ?
C2 N2 C1 122.1(4) . . ?
C2 N2 H2 119.0 . . ?
C1 N2 H2 119.0 . . ?
H1D O1 H1C 81.4 . . ?
H1D O1 H1F 110.5 . . ?
H1D O1 H1E 91.9 . . ?
N2 C2 C4 120.5(5) . . ?
N2 C2 H2A 119.7 . . ?
C4 C2 H2A 119.7 . . ?
N1 C7 C7 110.3(5) . 3_765 ?
N1 C7 H7A 109.6 . . ?
C7 C7 H7A 109.6 3_765 . ?
N1 C7 H7B 109.6 . . ?
C7 C7 H7B 109.6 3_765 . ?
H7A C7 H7B 108.1 . . ?
C4 C5 C3 119.3(4) . . ?
C4 C5 C6 122.1(4) . . ?
C3 C5 C6 118.6(4) . . ?
C2 C4 C5 119.0(5) . . ?
C2 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C1 C3 C5 119.0(5) . . ?
C1 C3 H3 120.5 . . ?
C5 C3 H3 120.5 . . ?
N1 C6 C5 112.4(4) . . ?
N1 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
N2 C1 C3 120.2(5) . . ?
N2 C1 H1 119.9 . . ?
C3 C1 H1 119.9 . . ?

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.110



####################################################################### 
# 
# 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_230919_l1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2283704'
loop_
_audit_author_name
_audit_author_address
'Li hai-tao'
;Heze University Liaoning  University
China
;
_audit_update_record             
;
2023-11-17 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
_audit_creation_date             2023-09-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Cu, 2(Cl), C14 H22 N4'
_chemical_formula_sum            'C14 H22 Cl6 Cu N4'
_chemical_formula_weight         522.59
_chemical_melting_point          ?
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'
Cu Cu 0.3201 1.2651 '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'

_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           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   9.1035(8)
_cell_length_b                   5.0596(4)
_cell_length_c                   23.3576(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.543(3)
_cell_angle_gamma                90
_cell_volume                     1073.80(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4761
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      29.85
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.741
_shelx_estimated_absorpt_T_min   0.719
_exptl_absorpt_coefficient_mu    1.770
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5661
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0831 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.7587.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             530
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9534
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.756
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1640
_reflns_number_total             1882
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.128
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1882
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.119
_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)+(0.0371P)²+2.5157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1034
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Others
 Sof(Cu1A)=0.5*(1-FVAR(2))
 Sof(Cu1)=0.5*FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cu1 Cu 0.000000 -0.14093(14) 0.250000 0.0300(2) Uani 0.963(2) 2 d S T P A 1
Cu1A Cu 0.000000 0.140(3) 0.250000 0.012(5) Uani 0.037(2) 2 d S T P A 2
Cl1 Cl -0.23240(11) -0.2821(2) 0.25442(4) 0.0407(3) Uani 1 1 d . . . . .
Cl2 Cl 0.02872(11) 0.0188(2) 0.34140(4) 0.0443(3) Uani 1 1 d . . . . .
Cl3 Cl 0.71807(11) 0.99809(18) 0.51247(4) 0.0367(3) Uani 1 1 d . . . . .
N1 N 0.3448(4) 0.2794(9) 0.35077(17) 0.0522(11) Uani 1 1 d . . . . .
H1 H 0.256334 0.226358 0.342311 0.063 Uiso 1 1 calc R U . . .
N2 N 0.8212(3) 0.5004(6) 0.45490(12) 0.0236(6) Uani 1 1 d . . . . .
H2A H 0.786388 0.347957 0.467401 0.028 Uiso 1 1 calc R U . . .
H2B H 0.779465 0.630465 0.473765 0.028 Uiso 1 1 calc R U . . .
C1 C 0.3651(5) 0.4835(10) 0.3866(2) 0.0466(12) Uani 1 1 d . . . . .
H1A H 0.285089 0.569312 0.401101 0.056 Uiso 1 1 calc R U . . .
C2 C 0.5058(4) 0.5642(9) 0.40146(17) 0.0379(10) Uani 1 1 d . . . . .
H2 H 0.521767 0.701204 0.427661 0.045 Uiso 1 1 calc R U . . .
C3 C 0.6237(4) 0.4449(8) 0.37811(15) 0.0292(8) Uani 1 1 d . . . . .
C4 C 0.5973(5) 0.2363(9) 0.34037(18) 0.0407(10) Uani 1 1 d . . . . .
H4 H 0.675172 0.152504 0.323832 0.049 Uiso 1 1 calc R U . . .
C5 C 0.4548(6) 0.1544(10) 0.3276(2) 0.0530(13) Uani 1 1 d . . . . .
H5 H 0.435698 0.012495 0.302953 0.064 Uiso 1 1 calc R U . . .
C6 C 0.7801(4) 0.5275(8) 0.39234(16) 0.0319(9) Uani 1 1 d . . . . .
H6A H 0.845290 0.419287 0.370846 0.038 Uiso 1 1 calc R U . . .
H6B H 0.792666 0.709996 0.380895 0.038 Uiso 1 1 calc R U . . .
C7 C 0.9840(4) 0.5089(8) 0.46771(15) 0.0293(8) Uani 1 1 d . . . . .
H7A H 1.023642 0.672337 0.453365 0.035 Uiso 1 1 calc R U . . .
H7B H 1.030298 0.362459 0.448962 0.035 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
Cu1 Cl1 2.2414(10) 2 ?
Cu1 Cl1 2.2415(10) . ?
Cu1 Cl2 2.2827(10) . ?
Cu1 Cl2 2.2827(10) 2 ?
Cu1A Cl2 2.221(4) 2 ?
Cu1A Cl2 2.221(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.334(6) . ?
N1 C5 1.327(7) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C6 1.492(5) . ?
N2 C7 1.495(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.369(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(6) . ?
C3 C4 1.386(6) . ?
C3 C6 1.502(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(7) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.521(7) 3_766 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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
Cl1 Cu1 Cl1 142.83(7) 2 . ?
Cl1 Cu1 Cl2 97.11(4) 2 2 ?
Cl1 Cu1 Cl2 95.85(4) . 2 ?
Cl1 Cu1 Cl2 95.85(4) 2 . ?
Cl1 Cu1 Cl2 97.11(4) . . ?
Cl2 Cu1 Cl2 138.52(7) . 2 ?
Cl2 Cu1A Cl2 147.9(7) 2 . ?
C1 N1 H1 118.5 . . ?
C5 N1 H1 118.5 . . ?
C5 N1 C1 123.0(4) . . ?
H2A N2 H2B 107.9 . . ?
C6 N2 H2A 109.2 . . ?
C6 N2 H2B 109.2 . . ?
C6 N2 C7 112.3(3) . . ?
C7 N2 H2A 109.2 . . ?
C7 N2 H2B 109.2 . . ?
N1 C1 H1A 120.6 . . ?
N1 C1 C2 118.8(4) . . ?
C2 C1 H1A 120.6 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 118.6(4) . . ?
C2 C3 C6 122.9(4) . . ?
C4 C3 C6 118.5(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 119.5(4) . . ?
N1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N2 C6 C3 111.6(3) . . ?
N2 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C3 C6 H6A 109.3 . . ?
C3 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 C7 108.9(4) . 3_766 ?
N2 C7 H7A 109.9 . . ?
N2 C7 H7B 109.9 . . ?
C7 C7 H7A 109.9 3_766 . ?
C7 C7 H7B 109.9 3_766 . ?
H7A C7 H7B 108.3 . . ?

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
N1 C1 C2 C3 2.8(7) . . . . ?
C1 N1 C5 C4 -0.2(7) . . . . ?
C1 C2 C3 C4 -1.8(6) . . . . ?
C1 C2 C3 C6 179.2(4) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C2 C3 C6 N2 59.7(5) . . . . ?
C3 C4 C5 N1 1.3(7) . . . . ?
C4 C3 C6 N2 -119.3(4) . . . . ?
C5 N1 C1 C2 -1.8(7) . . . . ?
C6 N2 C7 C7 177.8(4) . . . 3_766 ?
C6 C3 C4 C5 178.8(4) . . . . ?
C7 N2 C6 C3 164.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_231030_l1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2283705'
loop_
_audit_author_name
_audit_author_address
'Li hai-tao'
;Heze University Liaoning  University
China
;
_audit_update_record             
;
2023-10-30 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
_audit_creation_date             2023-10-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl4 Cu H2 O), C14 H22 N4'
_chemical_formula_sum            'C14 H26 Cl8 Cu2 N4 O2'
_chemical_formula_weight         693.07
_chemical_melting_point          ?
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'
Cu Cu 0.3201 1.2651 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3666(3)
_cell_length_b                   9.1403(5)
_cell_length_c                   11.6139(6)
_cell_angle_alpha                74.548(2)
_cell_angle_beta                 88.019(2)
_cell_angle_gamma                80.640(2)
_cell_volume                     642.71(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9308
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      30.60
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.634
_shelx_estimated_absorpt_T_min   0.573
_exptl_absorpt_coefficient_mu    2.506
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4763
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1074 before and 0.0430 after correction.
The Ratio of minimum to maximum transmission is 0.6384.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9903
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         2.342
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2157
_reflns_number_total             2270
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2270
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0238P)²+0.8163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0651
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H1B-H2A
 2.8 with sigma of 0.01
3.a Rotating group:
 O1(H1B,H1C)
3.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cu1 Cu 0.44124(5) 0.75343(4) 0.70166(3) 0.02792(11) Uani 1 1 d . . . . .
Cl1 Cl 0.50287(12) 0.87093(9) 0.84632(6) 0.04351(19) Uani 1 1 d . . . . .
Cl2 Cl 0.29700(10) 0.85604(7) 0.50223(6) 0.03278(16) Uani 1 1 d . . . . .
Cl3 Cl 0.58073(9) 0.48810(7) 0.69948(6) 0.03059(15) Uani 1 1 d . . . . .
Cl4 Cl 0.12795(10) 0.69363(9) 0.78442(6) 0.03997(18) Uani 1 1 d . . . . .
O1 O 0.7187(3) 0.8016(2) 0.62425(15) 0.0264(4) Uani 1 1 d . . . . .
H1B H 0.831100 0.768869 0.675998 0.040 Uiso 1 1 d DR U . . .
H1C H 0.722229 0.904426 0.600315 0.040 Uiso 1 1 d R U . . .
N1 N 1.1193(4) 0.7885(3) 0.03043(19) 0.0338(5) Uani 1 1 d . . . . .
H1 H 1.183874 0.787644 -0.035730 0.041 Uiso 1 1 calc R U . . .
N2 N 0.7547(3) 0.6365(2) 0.42680(18) 0.0270(4) Uani 1 1 d . . . . .
H2A H 0.698790 0.646923 0.496018 0.032 Uiso 1 1 calc DR U . . .
H2B H 0.651818 0.618258 0.385084 0.032 Uiso 1 1 calc R U . . .
C1 C 1.1901(4) 0.8632(3) 0.1015(2) 0.0337(6) Uani 1 1 d . . . . .
H1A H 1.305851 0.914486 0.078775 0.040 Uiso 1 1 calc R U . . .
C2 C 1.0916(4) 0.8642(3) 0.2082(2) 0.0307(6) Uani 1 1 d . . . . .
H2 H 1.139377 0.916953 0.257773 0.037 Uiso 1 1 calc R U . . .
C3 C 0.9201(4) 0.7862(3) 0.2419(2) 0.0251(5) Uani 1 1 d . . . . .
C4 C 0.8490(5) 0.7130(3) 0.1641(2) 0.0343(6) Uani 1 1 d . . . . .
H4 H 0.731656 0.662676 0.183613 0.041 Uiso 1 1 calc R U . . .
C5 C 0.9522(5) 0.7149(3) 0.0580(2) 0.0386(7) Uani 1 1 d . . . . .
H5 H 0.905930 0.665164 0.005665 0.046 Uiso 1 1 calc R U . . .
C6 C 0.8166(4) 0.7874(3) 0.3605(2) 0.0312(6) Uani 1 1 d . . . . .
H6A H 0.914247 0.815991 0.409873 0.037 Uiso 1 1 calc R U . . .
H6B H 0.690474 0.865412 0.347050 0.037 Uiso 1 1 calc R U . . .
C7 C 0.9228(4) 0.4971(3) 0.4532(2) 0.0289(5) Uani 1 1 d . . . . .
H7A H 0.999285 0.490580 0.380590 0.035 Uiso 1 1 calc R U . . .
H7B H 0.856483 0.405783 0.481126 0.035 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
Cu1 Cl1 2.2966(7) . ?
Cu1 Cl2 2.4076(7) . ?
Cu1 Cl3 2.4497(7) . ?
Cu1 Cl4 2.2678(7) . ?
Cu1 O1 2.0137(16) . ?
O1 H1B 0.9094 . ?
O1 H1C 0.9102 . ?
N1 H1 0.8600 . ?
N1 C1 1.333(4) . ?
N1 C5 1.335(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C6 1.497(3) . ?
N2 C7 1.495(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.371(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(4) . ?
C3 C4 1.386(4) . ?
C3 C6 1.507(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(4) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.507(5) 2_766 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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
Cl1 Cu1 Cl2 131.62(3) . . ?
Cl1 Cu1 Cl3 126.42(3) . . ?
Cl2 Cu1 Cl3 100.89(2) . . ?
Cl4 Cu1 Cl1 92.32(3) . . ?
Cl4 Cu1 Cl2 94.45(3) . . ?
Cl4 Cu1 Cl3 93.60(3) . . ?
O1 Cu1 Cl1 89.72(5) . . ?
O1 Cu1 Cl2 84.47(5) . . ?
O1 Cu1 Cl3 84.89(5) . . ?
O1 Cu1 Cl4 177.93(5) . . ?
Cu1 O1 H1B 112.9 . . ?
Cu1 O1 H1C 112.4 . . ?
H1B O1 H1C 101.0 . . ?
C1 N1 H1 118.7 . . ?
C1 N1 C5 122.6(2) . . ?
C5 N1 H1 118.7 . . ?
H2A N2 H2B 107.1 . . ?
C6 N2 H2A 107.7 . . ?
C6 N2 H2B 107.7 . . ?
C7 N2 H2A 107.7 . . ?
C7 N2 H2B 107.7 . . ?
C7 N2 C6 118.4(2) . . ?
N1 C1 H1A 120.1 . . ?
N1 C1 C2 119.7(2) . . ?
C2 C1 H1A 120.1 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C6 118.7(2) . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 C6 122.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 119.6(3) . . ?
N1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N2 C6 C3 113.8(2) . . ?
N2 C6 H6A 108.8 . . ?
N2 C6 H6B 108.8 . . ?
C3 C6 H6A 108.8 . . ?
C3 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
N2 C7 C7 111.0(3) . 2_766 ?
N2 C7 H7A 109.4 . . ?
N2 C7 H7B 109.4 . . ?
C7 C7 H7A 109.4 2_766 . ?
C7 C7 H7B 109.4 2_766 . ?
H7A C7 H7B 108.0 . . ?

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 0.6(4) . . . . ?
C1 N1 C5 C4 -1.0(4) . . . . ?
C1 C2 C3 C4 -2.0(4) . . . . ?
C1 C2 C3 C6 179.2(2) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
C2 C3 C6 N2 -140.0(2) . . . . ?
C3 C4 C5 N1 -0.5(5) . . . . ?
C4 C3 C6 N2 41.2(4) . . . . ?
C5 N1 C1 C2 0.9(4) . . . . ?
C6 N2 C7 C7 70.8(3) . . . 2_766 ?
C6 C3 C4 C5 -179.3(3) . . . . ?
C7 N2 C6 C3 56.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
