# Supplementary Information (SI) for ChemComm.
# 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_LYL_0916_1_410K
_audit_block_doi                 10.5517/ccdc.csd.cc2l4d7d
_database_code_depnum_ccdc_archive 'CCDC 2387503'
loop_
_audit_author_name
_audit_author_address
'Mao Wei-Xin'
;NanChang University
China
;
_audit_update_record             
;
2024-10-19 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;
_audit_creation_date             2024-09-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_formula_moiety         'Cl4 Cu, 2(C6 H9 N2)'
_chemical_formula_sum            'C12 H18 Cl4 Cu N4'
_chemical_formula_weight         423.659
_chemical_oxdiff_formula         'C H N Cu Cl '
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu -1.96878 0.60861 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19100 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   11.3440(9)
_cell_length_b                   12.2584(7)
_cell_length_c                   14.3901(13)
_cell_angle_alpha                90
_cell_angle_beta                 112.637(10)
_cell_angle_gamma                90
_cell_volume                     1846.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2974
_cell_measurement_temperature    410.00(10)
_cell_measurement_theta_max      71.6090
_cell_measurement_theta_min      3.3280
_exptl_absorpt_coefficient_mu    6.977
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38122
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'metallic greenish green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       block
_exptl_crystal_F_000             859.715
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.9600
_diffrn_reflns_Laue_measured_fraction_max 0.9600
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4407
_diffrn_reflns_point_group_measured_fraction_full 0.9600
_diffrn_reflns_point_group_measured_fraction_max 0.9600
_diffrn_reflns_theta_full        66.5940
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         5.56
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      410.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.9600
_diffrn_measured_fraction_theta_max 0.9600
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00  67.00   0.50    0.23    --   60.54-125.00-120.00   84
  2  ω     37.00  79.00   0.50    0.23    --   75.18 -94.00-120.00   84
  3  ω     39.00  69.00   0.50    0.23    --   60.54 -94.00 -90.00   60
  4  ω     36.00  93.00   0.50    0.23    --   75.18-125.00 -30.00  114
  5  ω     38.00  64.00   0.50    0.23    --   60.54 -94.00  90.00   52
  6  ω     43.00  82.00   0.50    0.23    --   75.18 -94.00 120.00   78
  7  ω     13.00  38.00   0.50    0.23    --   60.54 -30.00 120.00   50
  8  ω     11.00  38.00   0.50    0.23    --   60.54 -30.00  90.00   54
  9  ω     12.00  37.00   0.50    0.23    --   60.54 -30.00  30.00   50
 10  ω     12.00  38.00   0.50    0.23    --   60.54 -30.00-150.00   52
 11  ω     12.00  38.00   0.50    0.23    --   60.54 -30.00-180.00   52
 12  ω     40.00 114.00   0.50    0.23    --   75.12   0.00-180.00  148
 13  ω     75.00 101.00   0.50    0.23    --   60.54  30.00 -30.00   52
 14  ω     87.00 119.00   0.50    0.23    --   75.18  30.00  90.00   64
 15  ω     66.00 107.00   0.50    0.23    --   60.54  30.00  60.00   82
 16  ω    -90.00 -52.00   0.50    0.23    --  -60.72   0.00  30.00   76
 17  ω    -48.00 -22.00   0.50    0.23    --  -60.72   0.00  30.00   52
 18  ω    -67.00 -32.00   0.50    0.23    --  -75.50 125.00 -90.00   70
 19  ω    -77.00 -37.00   0.50    0.23    --  -75.50 125.00 150.00   80
 20  ω   -110.00 -35.00   0.50    0.23    --  -74.13   0.00 -60.00  150
 21  ω   -114.00 -76.00   0.50    0.23    --  -75.50 -30.00-150.00   76
 22  ω   -119.00 -94.00   0.50    0.23    --  -75.50-125.00-150.00   50
 23  ω   -114.00 -86.00   0.50    0.23    --  -74.13-125.00 -90.00   56
 24  ω   -117.00 -82.00   0.50    0.23    --  -75.50 -30.00  60.00   70
 25  ω   -123.00 -97.00   0.50    0.23    --  -74.13 -30.00 150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0628395000
_diffrn_orient_matrix_UB_12      0.0319937000
_diffrn_orient_matrix_UB_13      -0.1118936000
_diffrn_orient_matrix_UB_21      -0.1119949000
_diffrn_orient_matrix_UB_22      -0.0777584000
_diffrn_orient_matrix_UB_23      -0.0133106000
_diffrn_orient_matrix_UB_31      -0.0718020000
_diffrn_orient_matrix_UB_32      0.0934779000
_diffrn_orient_matrix_UB_33      0.0272404000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1159
_reflns_number_total             1562
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.129a 64-bit (release 29-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.4793
_refine_diff_density_min         -0.8202
_refine_diff_density_rms         0.1298
_refine_ls_d_res_high            0.8400
_refine_ls_d_res_low             7.9614
_refine_ls_goodness_of_fit_ref   1.0162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    15
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1562
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0690
_refine_ls_restrained_S_all      1.0162
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2029
_refine_ls_wR_factor_ref         0.2557
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C1(H1a), C2(H2)
2.b X=CH2 refined with riding coordinates:
 N2(H2a,H2b)
2.c Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 1.0 0.75301(6) 0.25 0.0794(5) Uani 1.000000 2 S T P
Cl1 Cl 0.94250(17) 0.87688(10) 0.33975(13) 0.1087(7) Uani 1.000000 1 . . .
Cl2 Cl 0.85297(15) 0.62886(11) 0.24651(17) 0.1186(8) Uani 1.000000 1 . . .
N1 N 0.6831(4) 0.7624(3) 0.3600(4) 0.0871(12) Uani 1.000000 1 . . .
H1 H 0.7477(4) 0.7511(3) 0.3441(4) 0.1045(15) Uiso 1.000000 1 R . .
C6 C 0.6167(4) 0.6763(4) 0.3715(3) 0.0770(11) Uani 1.000000 1 . . .
N2 N 0.6520(4) 0.5773(4) 0.3548(4) 0.1065(14) Uani 1.000000 1 . . .
H2a H 0.7159(4) 0.5697(4) 0.3371(4) 0.1278(17) Uiso 1.000000 1 R . .
H2b H 0.6111(4) 0.5209(4) 0.3617(4) 0.1278(17) Uiso 1.000000 1 R . .
C5 C 0.5157(5) 0.6969(4) 0.4001(4) 0.0841(12) Uani 1.000000 1 . . .
H5 H 0.4692(5) 0.6384(4) 0.4096(4) 0.1009(15) Uiso 1.000000 1 R . .
C3 C 0.4823(5) 0.7990(5) 0.4146(4) 0.0916(14) Uani 1.000000 1 . . .
C1 C 0.6519(6) 0.8650(5) 0.3726(5) 0.1023(16) Uani 1.000000 1 . . .
H1a H 0.6994(6) 0.9224(5) 0.3627(5) 0.123(2) Uiso 1.000000 1 R . .
C2 C 0.5541(6) 0.8861(5) 0.3988(5) 0.1062(17) Uani 1.000000 1 . . .
H2 H 0.5329(6) 0.9579(5) 0.4068(5) 0.127(2) Uiso 1.000000 1 R . .
C4 C 0.3715(7) 0.8216(7) 0.4449(6) 0.133(3) Uani 1.000000 1 . . .
H4a H 0.331(4) 0.7541(8) 0.449(5) 0.200(4) Uiso 1.000000 1 GR . .
H4b H 0.4018(10) 0.857(5) 0.509(2) 0.200(4) Uiso 1.000000 1 GR . .
H4c H 0.311(3) 0.868(4) 0.396(2) 0.200(4) Uiso 1.000000 1 GR . .


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 2.2467(12) . ?
Cu1 Cl1 2.2467(12) 2_755 ?
Cu1 Cl2 2.2441(13) . ?
Cu1 Cl2 2.2441(13) 2_755 ?
N1 H1 0.8600 . ?
N1 C6 1.343(6) . ?
N1 C1 1.338(7) . ?
C6 N2 1.328(6) . ?
C6 C5 1.382(7) . ?
N2 H2a 0.8600 . ?
N2 H2b 0.8600 . ?
C5 H5 0.9300 . ?
C5 C3 1.347(8) . ?
C3 C2 1.413(8) . ?
C3 C4 1.507(8) . ?
C1 H1a 0.9300 . ?
C1 C2 1.329(8) . ?
C2 H2 0.9300 . ?
C4 H4a 0.9600 . ?
C4 H4b 0.9600 . ?
C4 H4c 0.9600 . ?

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 94.96(7) 2_755 . ?
Cl2 Cu1 Cl1 95.36(5) 2_755 2_755 ?
Cl2 Cu1 Cl1 145.41(8) 2_755 . ?
Cl2 Cu1 Cl1 145.41(8) . 2_755 ?
Cl2 Cu1 Cl1 95.36(5) . . ?
Cl2 Cu1 Cl2 94.60(7) 2_755 . ?
C6 N1 H1 118.9(3) . . ?
C1 N1 H1 118.9(3) . . ?
C1 N1 C6 122.2(5) . . ?
N2 C6 N1 118.2(5) . . ?
C5 C6 N1 117.5(5) . . ?
C5 C6 N2 124.3(5) . . ?
H2a N2 C6 120.0 . . ?
H2b N2 C6 120.0 . . ?
H2b N2 H2a 120.0 . . ?
H5 C5 C6 119.0(3) . . ?
C3 C5 C6 122.0(5) . . ?
C3 C5 H5 119.0(3) . . ?
C2 C3 C5 117.7(5) . . ?
C4 C3 C5 122.1(6) . . ?
C4 C3 C2 120.2(6) . . ?
H1a C1 N1 119.5(3) . . ?
C2 C1 N1 121.0(5) . . ?
C2 C1 H1a 119.5(4) . . ?
C1 C2 C3 119.6(5) . . ?
H2 C2 C3 120.2(3) . . ?
H2 C2 C1 120.2(4) . . ?
H4a C4 C3 109.5 . . ?
H4b C4 C3 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 C3 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl1 0.8600 2.714(4) 3.373(4) 134.51(9) .
N1 H1 Cl2 0.8600 2.633(5) 3.389(5) 147.33(10) .
N2 H2a Cl1 0.8600 3.431(6) 3.566(5) 91.97(8) 6_645
N2 H2a Cl2 0.8600 2.491(5) 3.280(5) 152.83(11) .
N2 H2b Cl1 0.8600 3.245(6) 3.566(5) 105.01(9) 6_645
N2 H2b Cl1 0.8600 2.532(5) 3.367(5) 164.21(13) 5_445
C1 H1a Cl1 0.9300 2.954(6) 3.509(6) 119.67(11) .

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 C6 C5 C3 1.1(6) . . . . ?
N1 C1 C2 C3 0.5(8) . . . . ?
C6 C5 C3 C2 0.4(6) . . . . ?
C6 C5 C3 C4 179.5(6) . . . . ?
C5 C3 C2 C1 -1.2(6) . . . . ?


_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 9.304
_oxdiff_exptl_absorpt_empirical_full_min 0.264
####################################################################### 
# 
# 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_lyl_240406_5_300k-r
_audit_block_doi                 10.5517/ccdc.csd.cc2kwhsr
_database_code_depnum_ccdc_archive 'CCDC 2379925'
loop_
_audit_author_name
_audit_author_address
'Mao Wei-Xin'
;NanChang University
China
;
_audit_update_record             
;
2024-10-19 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;
_audit_creation_date             2024-05-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Cu, 2(C6 H9 N2)'
_chemical_formula_sum            'C12 H18 Cl4 Cu N4'
_chemical_formula_weight         423.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H  N O Cu Cl '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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                   13.3776(3)
_cell_length_b                   8.3515(2)
_cell_length_c                   15.9482(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.345(2)
_cell_angle_gamma                90
_cell_volume                     1778.75(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4008
_cell_measurement_temperature    299.12(10)
_cell_measurement_theta_max      76.0250
_cell_measurement_theta_min      6.2210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5781
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.238
_diffrn_reflns_theta_min         5.557
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.12(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  60.00   0.50    0.14    --  108.36 -61.00 -90.00   50
  2  ω     75.00 100.00   0.50    0.14    --  108.36 -77.00   0.00   50
  3  ω     38.00  67.00   0.50    0.14    --  108.36 -77.00   0.00   58
  4  ω     35.00  60.00   0.50    0.14    --  108.36 -61.00 -30.00   50
  5  ω     42.00  73.00   0.50    0.14    --  108.36 -61.00  60.00   62
  6  ω     35.00 101.00   0.50    0.14    --  108.36 -75.00 133.00  132
  7  ω    -12.00  22.00   0.50    0.05    --   45.20 -75.00 133.00   68
  8  ω    -25.00  25.00   0.50    0.05    --   45.20 -19.00 120.00  100
  9  ω    -29.00  27.00   0.50    0.05    --   45.20 -19.00 -30.00  112
 10  ω    120.00 178.00   0.50    0.14    --  108.36  77.00   0.00  116
 11  ω     85.00 163.00   0.50    0.14    --  108.36  75.00 -98.00  156
 12  ω     90.00 173.00   0.50    0.14    --  108.36  30.00-150.00  166
 13  ω     97.00 178.00   0.50    0.14    --  108.36  30.00-180.00  162
 14  ω     45.00  70.00   0.50    0.05    --   45.20  75.00 -98.00   50
 15  ω    -65.00  28.00   0.50    0.05    --  -45.20  75.00 -98.00  186
 16  ω    -64.00 -28.00   0.50    0.14    -- -102.00  61.00-120.00   72
 17  ω    -58.00 -28.00   0.50    0.14    -- -102.00  75.00 -98.00   60
 18  ω    -84.00 -59.00   0.50    0.14    -- -102.00  75.00 -98.00   50
 19  ω    -69.00 -28.00   0.50    0.14    -- -102.00  61.00 -30.00   82
 20  ω    -60.00 -32.00   0.50    0.14    -- -102.00  61.00  90.00   56
 21  ω    -69.00 -34.00   0.50    0.14    -- -102.00  61.00 120.00   70
 22  ω   -153.00-127.00   0.50    0.14    -- -102.00 -75.00 133.00   52
 23  ω   -100.00 -23.00   0.50    0.05    --  -45.20 -75.00 133.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0652017000
_diffrn_orient_matrix_UB_12      0.1430202000
_diffrn_orient_matrix_UB_13      0.0304677000
_diffrn_orient_matrix_UB_21      0.0152100000
_diffrn_orient_matrix_UB_22      0.0467873000
_diffrn_orient_matrix_UB_23      -0.0918517000
_diffrn_orient_matrix_UB_31      -0.0938727000
_diffrn_orient_matrix_UB_32      0.1068037000
_diffrn_orient_matrix_UB_33      -0.0006772000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1629
_reflns_number_total             1790
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.00058(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1790
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.083
_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)+(0.0611P)²+1.1832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1069
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C2(H2)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_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
Cu1 Cu 0.500000 0.49436(5) 0.250000 0.0445(2) Uani 1 2 d S T P . .
Cl1 Cl 0.62917(5) 0.57836(8) 0.33562(4) 0.0629(2) Uani 1 1 d . . . . .
Cl2 Cl 0.59370(5) 0.39414(8) 0.15111(5) 0.0655(2) Uani 1 1 d . . . . .
N1 N 0.62111(17) 0.2488(2) 0.44384(14) 0.0560(5) Uani 1 1 d . . . . .
H1 H 0.610029 0.337859 0.417823 0.067 Uiso 1 1 calc R U . . .
N2 N 0.70241(19) 0.1616(3) 0.32891(15) 0.0656(6) Uani 1 1 d . . . . .
H2A H 0.689542 0.251503 0.304338 0.079 Uiso 1 1 calc R U . . .
H2B H 0.735076 0.088762 0.303924 0.079 Uiso 1 1 calc R U . . .
C1 C 0.67177(18) 0.1350(3) 0.40561(16) 0.0490(5) Uani 1 1 d . . . . .
C4 C 0.60247(18) 0.0955(3) 0.56699(16) 0.0503(5) Uani 1 1 d . . . . .
C3 C 0.6547(2) -0.0257(3) 0.52774(19) 0.0564(6) Uani 1 1 d . . . . .
H3 H 0.667055 -0.121205 0.556490 0.068 Uiso 1 1 calc R U . . .
C6 C 0.5861(2) 0.2316(3) 0.52174(17) 0.0576(6) Uani 1 1 d . . . . .
H6 H 0.550136 0.314822 0.544436 0.069 Uiso 1 1 calc R U . . .
C2 C 0.6881(2) -0.0098(3) 0.4494(2) 0.0583(7) Uani 1 1 d . . . . .
H2 H 0.721500 -0.093805 0.424921 0.070 Uiso 1 1 calc R U . . .
C5 C 0.5670(3) 0.0772(4) 0.65393(19) 0.0683(7) Uani 1 1 d . . . . .
H5A H 0.552839 -0.033572 0.664276 0.103 Uiso 1 1 calc R U . . .
H5B H 0.507261 0.139317 0.659045 0.103 Uiso 1 1 calc R U . . .
H5C H 0.618044 0.113973 0.694137 0.103 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 2.2511(6) 2_655 ?
Cu1 Cl1 2.2511(6) . ?
Cu1 Cl2 2.2338(6) 2_655 ?
Cu1 Cl2 2.2338(6) . ?
N1 H1 0.8600 . ?
N1 C1 1.335(3) . ?
N1 C6 1.361(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.331(4) . ?
C1 C2 1.407(4) . ?
C4 C3 1.398(4) . ?
C4 C6 1.358(4) . ?
C4 C5 1.500(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.358(4) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

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 143.68(4) . 2_655 ?
Cl2 Cu1 Cl1 95.89(3) 2_655 2_655 ?
Cl2 Cu1 Cl1 95.89(3) . . ?
Cl2 Cu1 Cl1 97.52(3) 2_655 . ?
Cl2 Cu1 Cl1 97.53(3) . 2_655 ?
Cl2 Cu1 Cl2 135.99(4) . 2_655 ?
C1 N1 H1 118.2 . . ?
C1 N1 C6 123.6(2) . . ?
C6 N1 H1 118.2 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
N1 C1 C2 117.0(2) . . ?
N2 C1 N1 119.5(2) . . ?
N2 C1 C2 123.5(2) . . ?
C3 C4 C5 122.3(2) . . ?
C6 C4 C3 116.0(2) . . ?
C6 C4 C5 121.8(2) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 C4 122.7(2) . . ?
C2 C3 H3 118.6 . . ?
N1 C6 H6 119.3 . . ?
C4 C6 N1 121.3(2) . . ?
C4 C6 H6 119.3 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 Cl1 0.86 2.42 3.253(2) 163.3 . yes
N1 H1 Cl2 0.86 2.92 3.393(2) 116.9 2_655 yes
N2 H2B Cl2 0.86 2.87 3.525(3) 134.9 4_645 yes
C3 H3 Cl1 0.93 3.16 3.545(3) 107.1 7_656 yes
C2 H2 Cl2 0.93 2.82 3.504(3) 131.5 4_645 yes

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 -1.6(4) . . . . ?
N2 C1 C2 C3 179.6(3) . . . . ?
C1 N1 C6 C4 1.2(4) . . . . ?
C4 C3 C2 C1 1.2(4) . . . . ?
C3 C4 C6 N1 -1.7(4) . . . . ?
C6 N1 C1 N2 179.3(2) . . . . ?
C6 N1 C1 C2 0.5(4) . . . . ?
C6 C4 C3 C2 0.4(4) . . . . ?
C5 C4 C3 C2 -179.3(3) . . . . ?
C5 C4 C6 N1 178.1(3) . . . . ?

_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 2.786
_oxdiff_exptl_absorpt_empirical_full_min 0.488
####################################################################### 
# 
# 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_LYL_220916_1(230309)_R
_audit_block_doi                 10.5517/ccdc.csd.cc2kwhts
_database_code_depnum_ccdc_archive 'CCDC 2379926'
loop_
_audit_author_name
_audit_author_address
'Mao Wei-Xin'
;NanChang University
China
;
_audit_update_record             
;
2024-10-19 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;
_computing_data_collection       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_audit_creation_date             2024-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_formula_moiety         'Cl4 Cu, 2(C6 H9 N2)'
_chemical_formula_sum            'C12 H18 Cl4 Cu N4'
_chemical_formula_weight         423.659
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu 0.34125 1.28947 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19100 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   11.3689(18)
_cell_length_b                   12.3269(11)
_cell_length_c                   14.343(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.26(2)
_cell_angle_gamma                90
_cell_volume                     1846.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    2772
_cell_measurement_theta_min      2.5020
_cell_measurement_theta_max      27.4330
_exptl_absorpt_coefficient_mu    1.759
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'metallic greenish green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       block
_exptl_crystal_F_000             864.139
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9780
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14849
_diffrn_reflns_point_group_measured_fraction_full 0.9994
_diffrn_reflns_point_group_measured_fraction_max 0.9780
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         2.56
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9780
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                1628
_reflns_number_total             2620
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.7337
_refine_diff_density_min         -0.8522
_refine_diff_density_rms         0.1348
_refine_ls_d_res_high            0.7114
_refine_ls_d_res_low             7.9687
_refine_ls_goodness_of_fit_ref   1.0808
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    15
_refine_ls_number_parameters     98
_refine_ls_number_reflns         2620
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.0808
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0861P)²+3.0386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1843
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N2(H2a,H2b)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1a), C2(H2), C5(H5)
2.c Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.5 0.00056(5) 0.25 0.0498(2) Uani 1.000000 2 S T P
Cl1 Cl 0.64905(10) 0.12537(9) 0.33834(10) 0.0676(4) Uani 1.000000 1 . . .
Cl2 Cl 0.35585(11) -0.12389(9) 0.25445(12) 0.0735(4) Uani 1.000000 1 . . .
N1 N 0.4276(4) 0.5098(3) 0.3603(3) 0.0525(8) Uani 1.000000 1 . . .
H1 H 0.3473(4) 0.4987(3) 0.3442(3) 0.0630(10) Uiso 1.000000 1 R . .
N2 N 0.4544(4) 0.3228(3) 0.3535(3) 0.0659(10) Uani 1.000000 1 . . .
H2a H 0.481(3) 0.2869(10) 0.4094(7) 0.0791(13) Uiso 1.000000 1 GR . .
H2b H 0.3723(4) 0.3278(3) 0.329(3) 0.0791(13) Uiso 1.000000 1 GR . .
C1 C 0.4718(5) 0.6135(4) 0.3730(4) 0.0657(12) Uani 1.000000 1 . . .
H1a H 0.4147(5) 0.6707(4) 0.3629(4) 0.0789(15) Uiso 1.000000 1 R . .
C2 C 0.5979(5) 0.6344(4) 0.4003(4) 0.0664(12) Uani 1.000000 1 . . .
H2 H 0.6271(5) 0.7057(4) 0.4087(4) 0.0796(15) Uiso 1.000000 1 R . .
C3 C 0.6852(4) 0.5478(4) 0.4159(3) 0.0576(10) Uani 1.000000 1 . . .
C4 C 0.8276(5) 0.5684(6) 0.4491(5) 0.0865(17) Uani 1.000000 1 . . .
H4a H 0.8622(10) 0.595(4) 0.5175(13) 0.130(3) Uiso 1.000000 1 GR . .
H4b H 0.8697(9) 0.5019(10) 0.446(3) 0.130(3) Uiso 1.000000 1 GR . .
H4c H 0.8409(6) 0.621(3) 0.405(2) 0.130(3) Uiso 1.000000 1 GR . .
C5 C 0.6376(4) 0.4434(4) 0.4020(3) 0.0533(10) Uani 1.000000 1 . . .
H5 H 0.6935(4) 0.3853(4) 0.4127(3) 0.0640(12) Uiso 1.000000 1 R . .
C6 C 0.5057(4) 0.4233(3) 0.3720(3) 0.0469(8) Uani 1.000000 1 . . .


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 2.2689(12) 2_655 ?
Cu1 Cl1 2.2689(12) . ?
Cu1 Cl2 2.2640(11) . ?
Cu1 Cl2 2.2640(11) 2_655 ?
N1 H1 0.8600 . ?
N1 C1 1.359(6) . ?
N1 C6 1.354(5) . ?
N2 H2a 0.8595 . ?
N2 H2b 0.8599 . ?
N2 C6 1.351(5) . ?
C1 H1a 0.9300 . ?
C1 C2 1.354(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.414(7) . ?
C3 C4 1.517(7) . ?
C3 C5 1.380(6) . ?
C4 H4a 0.9600 . ?
C4 H4b 0.9600 . ?
C4 H4c 0.9600 . ?
C5 H5 0.9300 . ?
C5 C6 1.409(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
Cl1 Cu1 Cl1 94.61(6) . 2_655 ?
Cl2 Cu1 Cl1 146.41(6) . . ?
Cl2 Cu1 Cl1 94.93(4) 2_655 . ?
Cl2 Cu1 Cl1 94.93(4) . 2_655 ?
Cl2 Cu1 Cl1 146.41(6) 2_655 2_655 ?
Cl2 Cu1 Cl2 94.69(6) 2_655 . ?
C1 N1 H1 118.8(3) . . ?
C6 N1 H1 118.8(2) . . ?
C6 N1 C1 122.3(4) . . ?
H2b N2 H2a 109.5 . . ?
C6 N2 H2a 109.0 . . ?
C6 N2 H2b 109.2 . . ?
H1a C1 N1 119.6(3) . . ?
C2 C1 N1 120.7(4) . . ?
C2 C1 H1a 119.6(3) . . ?
H2 C2 C1 120.0(3) . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.0(3) . . ?
C4 C3 C2 121.3(5) . . ?
C5 C3 C2 118.1(4) . . ?
C5 C3 C4 120.7(5) . . ?
H4a C4 C3 109.5 . . ?
H4b C4 C3 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 C3 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?
H5 C5 C3 119.4(3) . . ?
C6 C5 C3 121.2(4) . . ?
C6 C5 H5 119.4(3) . . ?
N2 C6 N1 119.2(4) . . ?
C5 C6 N1 117.8(4) . . ?
C5 C6 N2 123.1(4) . . ?

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 -0.1(6) . . . . ?
N1 C6 C5 C3 -2.0(5) . . . . ?
N2 C6 C5 C3 177.2(4) . . . . ?
C1 C2 C3 C4 -178.5(5) . . . . ?
C1 C2 C3 C5 0.4(6) . . . . ?
C2 C3 C5 C6 0.7(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
