# Supplementary Information (SI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_2021-5-20-zq-5-8-1-2a
_database_code_depnum_ccdc_archive 'CCDC 2341002'
loop_
_audit_author_name
_audit_author_address
'Ruibing Lv'
;Institute of Chemical Materials, China Academy of Engineering Physics (CAEP)
China
;
_audit_update_record             
;
2024-03-18 deposited with the CCDC.	2024-10-10 downloaded from the CCDC.
;
_audit_creation_date             2021-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 Cu N14'
_chemical_formula_sum            'C4 H4 Cu N14'
_chemical_formula_weight         311.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cu C N H'
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'
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      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                   5.2475(6)
_cell_length_b                   5.9713(7)
_cell_length_c                   8.5316(11)
_cell_angle_alpha                73.990(11)
_cell_angle_beta                 73.570(11)
_cell_angle_gamma                76.141(10)
_cell_volume                     242.66(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1252
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7070
_cell_measurement_theta_min      3.9040
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.805
_exptl_absorpt_coefficient_mu    2.268
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.133
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             155
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3401
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.733
_diffrn_reflns_theta_min         3.605
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  60.00   1.00   11.00    --   18.58 -99.00-120.00   44
  2  ω    -10.00  89.00   1.00   11.00    --   18.58  77.00  30.00   99
  3  ω     44.00  87.00   1.00   11.00    --   18.58  57.00 -60.00   43
  4  ω     35.00  87.00   1.00   11.00    --   18.58 178.00  30.00   52
  5  ω    -20.00  58.00   1.00   11.00    --   18.58 -99.00 120.00   78
  6  ω    -11.00  84.00   1.00   11.00    --   18.58  77.00-120.00   95
  7  ω      1.00  83.00   1.00   11.00    --   18.58  57.00 150.00   82
  8  ω     -7.00  45.00   1.00   11.00    --  -18.81  77.00 150.00   52
  9  ω    -70.00 -35.00   1.00   11.00    --  -18.81-178.00 120.00   35
 10  ω    -49.00  45.00   1.00   11.00    --  -18.81  77.00   0.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0905682000
_diffrn_orient_matrix_UB_12      -0.0778511000
_diffrn_orient_matrix_UB_13      0.0125245000
_diffrn_orient_matrix_UB_21      -0.0849707000
_diffrn_orient_matrix_UB_22      0.0480272000
_diffrn_orient_matrix_UB_23      0.0681415000
_diffrn_orient_matrix_UB_31      -0.0711745000
_diffrn_orient_matrix_UB_32      0.0859510000
_diffrn_orient_matrix_UB_33      -0.0557455000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1010
_reflns_number_total             1127
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.036
_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)+(0.0310P)²+0.0360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0735
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1)
;
_atom_sites_solution_hydrogens   geom
_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
Cu1 Cu 1.000000 0.500000 0.500000 0.01726(16) Uani 1 2 d S T P . .
N4 N 0.9638(4) 0.6236(4) 0.7065(3) 0.0180(5) Uani 1 1 d . . . . .
N6 N 0.9805(4) 0.8201(4) 0.8809(3) 0.0159(5) Uani 1 1 d . . . . .
N2 N 0.5313(4) 0.7596(4) 0.3827(3) 0.0179(5) Uani 1 1 d . . . . .
N7 N 1.0828(5) 0.9678(4) 0.9395(3) 0.0182(5) Uani 1 1 d . . . . .
N1 N 0.7044(5) 0.7626(4) 0.4464(3) 0.0234(5) Uani 1 1 d . . . . .
N5 N 0.7315(5) 0.6094(4) 0.8362(3) 0.0236(5) Uani 1 1 d . . . . .
C2 C 1.1096(6) 0.7490(5) 0.7358(3) 0.0188(6) Uani 1 1 d . . . . .
H2 H 1.274922 0.784164 0.668539 0.023 Uiso 1 1 calc R . . . .
N3 N 0.3540(5) 0.7684(4) 0.3228(3) 0.0296(6) Uani 1 1 d . . . . .
C1 C 0.7460(5) 0.7300(5) 0.9383(3) 0.0203(6) Uani 1 1 d . . . . .
H1 H 0.616607 0.751771 1.035603 0.024 Uiso 1 1 calc R . . . .


_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 N4 2.036(2) . ?
Cu1 N4 2.036(2) 2_766 ?
Cu1 N1 1.979(2) . ?
Cu1 N1 1.979(2) 2_766 ?
N4 N5 1.397(3) . ?
N4 C2 1.302(3) . ?
N6 N7 1.392(3) . ?
N6 C2 1.360(3) . ?
N6 C1 1.369(3) . ?
N2 N1 1.189(3) . ?
N2 N3 1.166(3) . ?
N7 N7 1.233(4) 2_777 ?
N5 C1 1.301(3) . ?
C2 H2 0.9300 . ?
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
N4 Cu1 N4 180.00(10) . 2_766 ?
N1 Cu1 N4 93.15(9) 2_766 . ?
N1 Cu1 N4 93.15(9) . 2_766 ?
N1 Cu1 N4 86.85(9) . . ?
N1 Cu1 N4 86.85(9) 2_766 2_766 ?
N1 Cu1 N1 180.0 . 2_766 ?
N5 N4 Cu1 120.05(16) . . ?
C2 N4 Cu1 130.8(2) . . ?
C2 N4 N5 108.5(2) . . ?
C2 N6 N7 121.6(2) . . ?
C2 N6 C1 106.3(2) . . ?
C1 N6 N7 132.0(2) . . ?
N3 N2 N1 176.2(3) . . ?
N7 N7 N6 110.2(3) 2_777 . ?
N2 N1 Cu1 127.06(18) . . ?
C1 N5 N4 106.7(2) . . ?
N4 C2 N6 108.8(2) . . ?
N4 C2 H2 125.6 . . ?
N6 C2 H2 125.6 . . ?
N6 C1 H1 125.1 . . ?
N5 C1 N6 109.7(2) . . ?
N5 C1 H1 125.1 . . ?


_olex2_date_sample_data_collection 2021-06-20
_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 1.126
_oxdiff_exptl_absorpt_empirical_full_min 0.876
