# Electronic Supplementary Material (ESI) 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_230413_teacu_100k
_database_code_depnum_ccdc_archive 'CCDC 2337198'
loop_
_audit_author_name
_audit_author_address
'Ryo Ohtani'
;Kyushu university
Japan
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-04-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C4 Cu4 N8), C8 H20 N'
_chemical_formula_sum            'C10 H20 Cu2 N5'
_chemical_formula_weight         337.39
_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'
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      orthorhombic
_space_group_IT_number           72
_space_group_name_H-M_alt        'I b a m'
_space_group_name_Hall           '-I 2 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1, y+1, -z+1/2'
'x+1, -y+1, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'x, -y, z+1/2'
'-x, y, z+1/2'

_cell_length_a                   14.9083(10)
_cell_length_b                   8.1008(5)
_cell_length_c                   12.1620(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1468.79(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5877
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.79
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.796
_shelx_estimated_absorpt_T_min   0.374
_exptl_absorpt_coefficient_mu    2.883
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1016 before and 0.0688 after correction.
The Ratio of minimum to maximum transmission is 0.7299.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             692
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.0570
0.00 -1.00 -1.00 0.0410
1.00 -1.00 0.00 0.0250
-1.00 0.00 -1.00 0.0670
1.00 0.00 1.00 0.1490
0.00 0.00 1.00 0.2120
-1.00 0.00 1.00 0.1990
1.00 0.00 -1.00 0.0230
-1.00 0.00 0.00 0.0640
1.00 0.00 0.00 0.0080
0.00 1.00 0.00 0.0260
-1.00 1.00 -1.00 0.0590

_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.083
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5857
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.876
_diffrn_reflns_theta_min         2.733
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                851
_reflns_number_total             916
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         916
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      1.128
_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)+(0.0252P)²+1.8954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0676
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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 0.34597(2) 0.11774(4) 0.500000 0.02705(14) Uani 1 2 d S T P . .
N3 N 0.500000 0.500000 0.750000 0.0205(6) Uani 1 4 d S T P . .
N1 N 0.24690(15) 0.4467(3) 0.500000 0.0290(5) Uani 1 2 d S T P . .
N2 N 0.46452(15) 0.0319(3) 0.500000 0.0322(5) Uani 1 2 d S T P . .
C1 C 0.29378(16) 0.3316(3) 0.500000 0.0214(5) Uani 1 2 d S T P . .
C2 C 0.44286(12) 0.3942(2) 0.82604(15) 0.0271(4) Uani 1 1 d . . . . .
H2A H 0.483339 0.331150 0.875059 0.032 Uiso 1 1 calc R U . . .
H2B H 0.406466 0.468268 0.872936 0.032 Uiso 1 1 calc R U . . .
C3 C 0.38049(15) 0.2738(3) 0.76966(18) 0.0447(5) Uani 1 1 d . . . . .
H3A H 0.415631 0.197262 0.724482 0.067 Uiso 1 1 calc R U . . .
H3B H 0.338436 0.334511 0.722773 0.067 Uiso 1 1 calc R U . . .
H3C H 0.346966 0.211460 0.825182 0.067 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 N1 1.959(2) 3_546 ?
Cu1 N2 1.899(2) . ?
Cu1 C1 1.899(2) . ?
N3 C2 1.5218(17) 2_665 ?
N3 C2 1.5218(17) . ?
N3 C2 1.5218(17) 7_546 ?
N3 C2 1.5218(17) 8_456 ?
N1 C1 1.165(4) . ?
N2 N2 1.177(5) 9_656 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.512(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?

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
N2 Cu1 N1 113.50(9) . 3_546 ?
C1 Cu1 N1 110.84(10) . 3_546 ?
C1 Cu1 N2 135.66(10) . . ?
C2 N3 C2 111.42(14) 2_665 8_456 ?
C2 N3 C2 111.42(14) 7_546 . ?
C2 N3 C2 105.15(15) 2_665 . ?
C2 N3 C2 105.15(15) 8_456 7_546 ?
C2 N3 C2 111.93(14) 2_665 7_546 ?
C2 N3 C2 111.93(14) 8_456 . ?
C1 N1 Cu1 171.9(2) . 3_556 ?
N2 N2 Cu1 175.4(3) 9_656 . ?
N1 C1 Cu1 167.3(2) . . ?
N3 C2 H2A 108.4 . . ?
N3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 N3 115.60(14) . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

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 Cu1 C1 N1 0.0 3_546 . . . ?
N2 Cu1 C1 N1 180.0 . . . . ?
C2 N3 C2 C3 -178.83(19) 2_665 . . . ?
C2 N3 C2 C3 -57.38(15) 7_546 . . . ?
C2 N3 C2 C3 60.04(15) 8_456 . . . ?

_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_230413_teacu_150k
_database_code_depnum_ccdc_archive 'CCDC 2337199'
loop_
_audit_author_name
_audit_author_address
'Ryo Ohtani'
;Kyushu university
Japan
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-04-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C4 Cu4 N8), C8 H20 N'
_chemical_formula_sum            'C10 H20 Cu2 N5'
_chemical_formula_weight         337.39
_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'
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      orthorhombic
_space_group_IT_number           72
_space_group_name_H-M_alt        'I b a m'
_space_group_name_Hall           '-I 2 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1, y+1, -z+1/2'
'x+1, -y+1, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'x, -y, z+1/2'
'-x, y, z+1/2'

_cell_length_a                   14.8851(8)
_cell_length_b                   8.1225(4)
_cell_length_c                   12.2203(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1477.49(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5696
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      29.54
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.709
_shelx_estimated_absorpt_T_min   0.391
_exptl_absorpt_coefficient_mu    2.866
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0866 before and 0.0653 after correction.
The Ratio of minimum to maximum transmission is 0.7338.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             692
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 -1.00 1.00 0.0560
1.00 -1.00 1.00 0.0720
0.00 -1.00 -1.00 0.1670
0.00 -1.00 0.00 0.0670
1.00 -1.00 0.00 0.0640
1.00 0.00 1.00 0.0520
-1.00 0.00 -1.00 0.1490
0.00 0.00 -1.00 0.2040
1.00 0.00 -1.00 0.1710
1.00 0.00 0.00 0.0620
-1.00 0.00 0.00 0.0080
-1.00 1.00 -1.00 0.1070
0.00 1.00 1.00 0.0570
1.00 1.00 1.00 0.0580
0.00 1.00 0.00 0.0340

_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.129
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5884
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.848
_diffrn_reflns_theta_min         2.737
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                832
_reflns_number_total             917
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         917
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.092
_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)+(0.0319P)²+1.4252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0717
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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 0.34540(2) 0.11537(4) 0.500000 0.03633(15) Uani 1 2 d S T P . .
N3 N 0.500000 0.500000 0.750000 0.0299(6) Uani 1 4 d S T P . .
N1 N 0.24693(15) 0.4443(3) 0.500000 0.0389(5) Uani 1 2 d S T P . .
N2 N 0.46427(16) 0.0312(3) 0.500000 0.0431(5) Uani 1 2 d S T P . .
C1 C 0.29311(16) 0.3286(3) 0.500000 0.0299(5) Uani 1 2 d S T P . .
C2 C 0.44281(13) 0.3945(2) 0.82555(16) 0.0397(5) Uani 1 1 d . . . . .
H2A H 0.483292 0.331703 0.874406 0.048 Uiso 1 1 calc R U . . .
H2B H 0.406236 0.468365 0.872140 0.048 Uiso 1 1 calc R U . . .
C3 C 0.38045(17) 0.2743(3) 0.7690(2) 0.0656(7) Uani 1 1 d . . . . .
H3A H 0.415772 0.198598 0.723776 0.098 Uiso 1 1 calc R U . . .
H3B H 0.338206 0.335019 0.722569 0.098 Uiso 1 1 calc R U . . .
H3C H 0.347014 0.211594 0.824081 0.098 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 N1 1.954(2) 3_546 ?
Cu1 N2 1.897(2) . ?
Cu1 C1 1.899(3) . ?
N3 C2 1.5201(18) 2_665 ?
N3 C2 1.5201(18) . ?
N3 C2 1.5201(18) 7_546 ?
N3 C2 1.5201(18) 8_456 ?
N1 C1 1.164(4) . ?
N2 N2 1.178(5) 9_656 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.514(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?

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
N2 Cu1 N1 113.56(9) . 3_546 ?
N2 Cu1 C1 135.33(10) . . ?
C1 Cu1 N1 111.11(10) . 3_546 ?
C2 N3 C2 111.40(15) 2_665 8_456 ?
C2 N3 C2 111.40(15) 7_546 . ?
C2 N3 C2 105.21(16) 2_665 . ?
C2 N3 C2 105.21(16) 8_456 7_546 ?
C2 N3 C2 111.89(14) 8_456 . ?
C2 N3 C2 111.89(14) 2_665 7_546 ?
C1 N1 Cu1 171.5(2) . 3_556 ?
N2 N2 Cu1 175.7(3) 9_656 . ?
N1 C1 Cu1 168.0(2) . . ?
N3 C2 H2A 108.4 . . ?
N3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 N3 115.44(15) . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

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 Cu1 C1 N1 0.0 3_546 . . . ?
N2 Cu1 C1 N1 180.0 . . . . ?
C2 N3 C2 C3 -178.7(2) 2_665 . . . ?
C2 N3 C2 C3 -57.32(16) 7_546 . . . ?
C2 N3 C2 C3 60.14(17) 8_456 . . . ?

_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_230413_teacu_350k
_database_code_depnum_ccdc_archive 'CCDC 2337200'
loop_
_audit_author_name
_audit_author_address
'Ryo Ohtani'
;Kyushu university
Japan
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-04-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C4 Cu4 N8), C8 H20 N'
_chemical_formula_sum            'C10 H20 Cu2 N5'
_chemical_formula_weight         337.39
_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'
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      orthorhombic
_space_group_IT_number           72
_space_group_name_H-M_alt        'I b a m'
_space_group_name_Hall           '-I 2 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1, y+1, -z+1/2'
'x+1, -y+1, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'x, -y, z+1/2'
'-x, y, z+1/2'

_cell_length_a                   14.7778(10)
_cell_length_b                   8.2376(6)
_cell_length_c                   12.5337(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1525.77(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4315
_cell_measurement_temperature    350.0
_cell_measurement_theta_max      25.79
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.784
_shelx_estimated_absorpt_T_min   0.459
_exptl_absorpt_coefficient_mu    2.775
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0980 before and 0.0629 after correction.
The Ratio of minimum to maximum transmission is 0.7824.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             692
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -1.00 0.00 0.0480
-1.00 -1.00 -1.00 0.1110
0.00 -1.00 1.00 0.1040
0.00 -1.00 0.00 0.0600
-1.00 0.00 0.00 0.0460
1.00 0.00 0.00 0.0160
-1.00 0.00 1.00 0.0910
1.00 0.00 -1.00 0.1310
0.00 0.00 -1.00 0.1660
-1.00 1.00 1.00 0.0680
0.00 1.00 -1.00 0.0930
0.00 1.00 1.00 0.0760
0.00 1.00 0.00 0.0200

_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.092
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5790
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         2.757
_diffrn_ambient_temperature      350.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.984
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                667
_reflns_number_total             779
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         779
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.049
_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)+(0.0430P)²+1.0916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0930
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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 0.65780(3) 0.10087(6) 0.500000 0.0850(3) Uani 1 2 d S T P . .
C1 C 0.7096(2) 0.3111(4) 0.500000 0.0779(9) Uani 1 2 d S T P . .
N3 N 0.500000 0.500000 0.250000 0.0777(11) Uani 1 4 d S T P . .
N1 N 0.7531(3) 0.4261(4) 0.500000 0.0956(10) Uani 1 2 d S T P . .
N2 N 0.5364(2) 0.0268(5) 0.500000 0.1009(11) Uani 1 2 d S T P . .
C2 C 0.5576(2) 0.3953(4) 0.1769(3) 0.1107(12) Uani 1 1 d . . . . .
H2A H 0.517599 0.332929 0.131238 0.133 Uiso 1 1 calc R U . . .
H2B H 0.593032 0.466117 0.131407 0.133 Uiso 1 1 calc R U . . .
C3 C 0.6206(3) 0.2802(7) 0.2320(5) 0.186(3) Uani 1 1 d . . . . .
H3A H 0.656251 0.223833 0.179729 0.279 Uiso 1 1 calc R U . . .
H3B H 0.586190 0.203169 0.272658 0.279 Uiso 1 1 calc R U . . .
H3C H 0.659837 0.339821 0.278800 0.279 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 C1 1.893(4) . ?
Cu1 N1 1.952(4) 3_646 ?
Cu1 N2 1.896(3) . ?
C1 N1 1.144(5) . ?
N3 C2 1.519(3) . ?
N3 C2 1.519(3) 2_665 ?
N3 C2 1.519(3) 8_455 ?
N3 C2 1.519(3) 7_545 ?
N2 N2 1.162(7) 9_656 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.497(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 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
C1 Cu1 N1 113.69(15) . 3_646 ?
C1 Cu1 N2 132.63(16) . . ?
N2 Cu1 N1 113.69(15) . 3_646 ?
N1 C1 Cu1 169.7(3) . . ?
C2 N3 C2 111.9(3) 2_665 7_545 ?
C2 N3 C2 110.8(3) . 7_545 ?
C2 N3 C2 105.8(3) 8_455 7_545 ?
C2 N3 C2 110.8(3) 8_455 2_665 ?
C2 N3 C2 111.9(3) . 8_455 ?
C2 N3 C2 105.8(3) . 2_665 ?
C1 N1 Cu1 171.7(3) . 3_656 ?
N2 N2 Cu1 176.4(5) 9_656 . ?
N3 C2 H2A 108.4 . . ?
N3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 N3 115.5(3) . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

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 Cu1 C1 N1 0.0 3_646 . . . ?
N2 Cu1 C1 N1 180.0 . . . . ?
C2 N3 C2 C3 -179.9(4) 2_665 . . . ?
C2 N3 C2 C3 -58.5(3) 7_545 . . . ?
C2 N3 C2 C3 59.4(3) 8_455 . . . ?

_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_230413_teacu_300k
_database_code_depnum_ccdc_archive 'CCDC 2337201'
loop_
_audit_author_name
_audit_author_address
'Ryo Ohtani'
;Kyushu university
Japan
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-04-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C4 Cu4 N8), C8 H20 N'
_chemical_formula_sum            'C10 H20 Cu2 N5'
_chemical_formula_weight         337.39
_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'
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      orthorhombic
_space_group_IT_number           72
_space_group_name_H-M_alt        'I b a m'
_space_group_name_Hall           '-I 2 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1, y+1, -z+1/2'
'x+1, -y+1, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'x, -y, z+1/2'
'-x, y, z+1/2'

_cell_length_a                   14.8065(7)
_cell_length_b                   8.2051(3)
_cell_length_c                   12.4448(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1511.90(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4993
_cell_measurement_temperature    300.0
_cell_measurement_theta_max      27.16
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   0.741
_shelx_estimated_absorpt_T_min   0.520
_exptl_absorpt_coefficient_mu    2.801
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0998 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.7721.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             692
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 -1.00 0.00 0.0090
1.00 -1.00 -1.00 0.0740
0.00 -1.00 0.00 0.0200
0.00 0.00 1.00 0.1230
1.00 0.00 -1.00 0.0940
-1.00 0.00 -1.00 0.0840
1.00 0.00 1.00 0.1280
-1.00 0.00 0.00 0.0020
1.00 0.00 0.00 0.0650
1.00 1.00 1.00 0.1000
1.00 1.00 -1.00 0.0590
1.00 1.00 0.00 0.0830
-1.00 1.00 1.00 0.0970
0.00 1.00 0.00 0.0720

_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.114
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5802
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.751
_diffrn_ambient_temperature      300.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                711
_reflns_number_total             805
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         805
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.065
_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)+(0.0466P)²+0.8524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0883
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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 0.34326(3) 0.89405(5) 0.500000 0.0701(2) Uani 1 2 d S T P . .
N3 N 0.500000 0.500000 0.750000 0.0641(9) Uani 1 4 d S T P . .
N1 N 0.2467(2) 0.5676(4) 0.500000 0.0783(8) Uani 1 2 d S T P . .
N2 N 0.46360(19) 0.9720(4) 0.500000 0.0825(8) Uani 1 2 d S T P . .
C1 C 0.2911(2) 0.6833(4) 0.500000 0.0629(7) Uani 1 2 d S T P . .
C2 C 0.44222(19) 0.6047(3) 0.8238(2) 0.0872(9) Uani 1 1 d . . . . .
H2A H 0.406386 0.533268 0.868894 0.105 Uiso 1 1 calc R U . . .
H2B H 0.481977 0.666389 0.870531 0.105 Uiso 1 1 calc R U . . .
C3 C 0.3797(3) 0.7219(6) 0.7684(3) 0.1470(19) Uani 1 1 d . . . . .
H3A H 0.337224 0.662229 0.725430 0.220 Uiso 1 1 calc R U . . .
H3B H 0.414156 0.793452 0.723177 0.220 Uiso 1 1 calc R U . . .
H3C H 0.347843 0.784832 0.821215 0.220 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 N1 1.950(3) 3_556 ?
Cu1 N2 1.893(3) . ?
Cu1 C1 1.894(3) . ?
N3 C2 1.521(2) 8_456 ?
N3 C2 1.521(2) . ?
N3 C2 1.521(2) 2_665 ?
N3 C2 1.521(2) 7_546 ?
N1 C1 1.154(5) . ?
N2 N2 1.172(6) 9_676 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.502(5) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 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
N2 Cu1 N1 113.37(13) . 3_556 ?
N2 Cu1 C1 133.80(14) . . ?
C1 Cu1 N1 112.83(13) . 3_556 ?
C2 N3 C2 105.7(2) 8_456 7_546 ?
C2 N3 C2 105.7(2) 2_665 . ?
C2 N3 C2 111.6(2) 8_456 . ?
C2 N3 C2 111.6(2) 7_546 2_665 ?
C2 N3 C2 111.2(2) 7_546 . ?
C2 N3 C2 111.2(2) 8_456 2_665 ?
C1 N1 Cu1 171.6(3) . 3_546 ?
N2 N2 Cu1 176.6(4) 9_676 . ?
N1 C1 Cu1 169.4(3) . . ?
N3 C2 H2A 108.4 . . ?
N3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 N3 115.6(2) . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

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 Cu1 C1 N1 0.0 3_556 . . . ?
N2 Cu1 C1 N1 180.0 . . . . ?
C2 N3 C2 C3 -59.9(3) 8_456 . . . ?
C2 N3 C2 C3 179.1(3) 2_665 . . . ?
C2 N3 C2 C3 57.8(3) 7_546 . . . ?

_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_230413_teacu_200k
_database_code_depnum_ccdc_archive 'CCDC 2337202'
loop_
_audit_author_name
_audit_author_address
'Ryo Ohtani'
;Kyushu university
Japan
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-04-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C4 Cu4 N8), C8 H20 N'
_chemical_formula_sum            'C10 H20 Cu2 N5'
_chemical_formula_weight         337.39
_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'
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      orthorhombic
_space_group_IT_number           72
_space_group_name_H-M_alt        'I b a m'
_space_group_name_Hall           '-I 2 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1, y+1, -z+1/2'
'x+1, -y+1, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'x, -y, z+1/2'
'-x, y, z+1/2'

_cell_length_a                   14.8624(4)
_cell_length_b                   8.1463(2)
_cell_length_c                   12.2872(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1487.66(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5565
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.826
_shelx_estimated_absorpt_T_min   0.384
_exptl_absorpt_coefficient_mu    2.846
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0883 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.7371.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             692
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -1.00 0.00 0.0500
0.00 -1.00 0.00 0.0550
-1.00 0.00 -1.00 0.1540
-1.00 0.00 0.00 0.0330
1.00 0.00 0.00 0.0350
0.00 0.00 1.00 0.0360
0.00 0.00 -1.00 0.2080
-1.00 1.00 0.00 0.0320
0.00 1.00 0.00 0.0250

_exptl_crystal_size_max          0.416
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5963
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.848
_diffrn_reflns_theta_min         2.741
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                823
_reflns_number_total             922
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.065
_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)+(0.0419P)²+1.4195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0837
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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 0.65524(2) 0.11271(4) 0.500000 0.04626(18) Uani 1 2 d S T P . .
N3 N 0.500000 0.500000 0.250000 0.0402(7) Uani 1 4 d S T P . .
N1 N 0.75311(17) 0.4404(3) 0.500000 0.0497(6) Uani 1 2 d S T P . .
N2 N 0.53597(17) 0.0304(3) 0.500000 0.0536(6) Uani 1 2 d S T P . .
C1 C 0.70756(18) 0.3252(3) 0.500000 0.0397(6) Uani 1 2 d S T P . .
C2 C 0.55739(15) 0.3948(3) 0.17495(18) 0.0536(6) Uani 1 1 d . . . . .
H2A H 0.516912 0.331729 0.126530 0.064 Uiso 1 1 calc R U . . .
H2B H 0.593866 0.468436 0.128425 0.064 Uiso 1 1 calc R U . . .
C3 C 0.6200(2) 0.2757(5) 0.2315(3) 0.0880(10) Uani 1 1 d . . . . .
H3A H 0.653893 0.213449 0.176828 0.132 Uiso 1 1 calc R U . . .
H3B H 0.584775 0.199773 0.276285 0.132 Uiso 1 1 calc R U . . .
H3C H 0.662024 0.336609 0.277821 0.132 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 N1 1.956(3) 3_646 ?
Cu1 N2 1.895(3) . ?
Cu1 C1 1.898(3) . ?
N3 C2 1.520(2) 8_455 ?
N3 C2 1.520(2) . ?
N3 C2 1.520(2) 7_545 ?
N3 C2 1.520(2) 2_665 ?
N1 C1 1.157(4) . ?
N2 N2 1.179(5) 9_656 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.514(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?

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
N2 Cu1 N1 113.43(11) . 3_646 ?
N2 Cu1 C1 134.90(12) . . ?
C1 Cu1 N1 111.67(11) . 3_646 ?
C2 N3 C2 111.42(18) 8_455 2_665 ?
C2 N3 C2 111.42(18) 7_545 . ?
C2 N3 C2 111.76(17) 8_455 . ?
C2 N3 C2 111.76(17) 2_665 7_545 ?
C2 N3 C2 105.32(19) 2_665 . ?
C2 N3 C2 105.32(19) 8_455 7_545 ?
C1 N1 Cu1 171.7(2) . 3_656 ?
N2 N2 Cu1 175.8(3) 9_656 . ?
N1 C1 Cu1 168.4(2) . . ?
N3 C2 H2A 108.4 . . ?
N3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 N3 115.35(18) . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

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 Cu1 C1 N1 0.0 3_646 . . . ?
N2 Cu1 C1 N1 180.0 . . . . ?
C2 N3 C2 C3 59.9(2) 8_455 . . . ?
C2 N3 C2 C3 -57.6(2) 7_545 . . . ?
C2 N3 C2 C3 -178.9(3) 2_665 . . . ?

_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_230413_teacu_250k
_database_code_depnum_ccdc_archive 'CCDC 2337204'
loop_
_audit_author_name
_audit_author_address
'Ryo Ohtani'
;Kyushu university
Japan
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-04-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C4 Cu4 N8), C8 H20 N'
_chemical_formula_sum            'C10 H20 Cu2 N5'
_chemical_formula_weight         337.39
_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'
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      orthorhombic
_space_group_IT_number           72
_space_group_name_H-M_alt        'I b a m'
_space_group_name_Hall           '-I 2 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1, y+1, -z+1/2'
'x+1, -y+1, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'x, -y, z+1/2'
'-x, y, z+1/2'

_cell_length_a                   14.8279(4)
_cell_length_b                   8.1752(2)
_cell_length_c                   12.3660(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1499.02(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5284
_cell_measurement_temperature    250.0
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   0.773
_shelx_estimated_absorpt_T_min   0.505
_exptl_absorpt_coefficient_mu    2.825
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0917 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.7776.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             692
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 -1.00 -1.00 0.0590
0.00 -1.00 -1.00 0.0580
0.00 -1.00 0.00 0.0140
-1.00 0.00 1.00 0.1170
-1.00 0.00 -1.00 0.0780
1.00 0.00 1.00 0.1260
0.00 0.00 1.00 0.1400
1.00 0.00 -1.00 0.0960
1.00 0.00 0.00 0.0480
-1.00 0.00 0.00 0.0260
1.00 1.00 -1.00 0.0680
0.00 1.00 0.00 0.0600

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.096
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5845
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.721
_diffrn_reflns_theta_min         2.747
_diffrn_ambient_temperature      250.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.981
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                746
_reflns_number_total             823
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.050
_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     47
_refine_ls_number_reflns         823
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.097
_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)+(0.0384P)²+1.1742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0819
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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 0.65588(3) 0.88985(5) 0.500000 0.0572(2) Uani 1 2 d S T P . .
N3 N 0.500000 0.500000 0.250000 0.0510(8) Uani 1 4 d S T P . .
N1 N 0.75317(19) 0.5628(4) 0.500000 0.0625(7) Uani 1 2 d S T P . .
N2 N 0.53623(18) 0.9708(4) 0.500000 0.0680(8) Uani 1 2 d S T P . .
C1 C 0.70829(19) 0.6786(4) 0.500000 0.0497(7) Uani 1 2 d S T P . .
C2 C 0.55757(17) 0.6049(3) 0.1757(2) 0.0686(7) Uani 1 1 d . . . . .
H2A H 0.593666 0.532455 0.129779 0.082 Uiso 1 1 calc R U . . .
H2B H 0.517449 0.667553 0.128263 0.082 Uiso 1 1 calc R U . . .
C3 C 0.6203(2) 0.7228(5) 0.2318(3) 0.1142(14) Uani 1 1 d . . . . .
H3A H 0.653790 0.784496 0.178167 0.171 Uiso 1 1 calc R U . . .
H3B H 0.662034 0.662347 0.277107 0.171 Uiso 1 1 calc R U . . .
H3C H 0.585439 0.797402 0.276239 0.171 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 N1 1.954(3) 3_656 ?
Cu1 N2 1.894(3) . ?
Cu1 C1 1.894(3) . ?
N3 C2 1.519(2) 2_665 ?
N3 C2 1.519(2) . ?
N3 C2 1.519(2) 7_545 ?
N3 C2 1.519(2) 8_455 ?
N1 C1 1.157(4) . ?
N2 N2 1.176(6) 9_676 ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 C3 1.508(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 H3C 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
N2 Cu1 N1 113.17(12) . 3_656 ?
N2 Cu1 C1 134.70(13) . . ?
C1 Cu1 N1 112.13(12) . 3_656 ?
C2 N3 C2 111.2(2) 2_665 8_455 ?
C2 N3 C2 111.2(2) 7_545 . ?
C2 N3 C2 105.6(2) 2_665 . ?
C2 N3 C2 105.6(2) 8_455 7_545 ?
C2 N3 C2 111.63(19) 8_455 . ?
C2 N3 C2 111.63(19) 2_665 7_545 ?
C1 N1 Cu1 171.5(3) . 3_646 ?
N2 N2 Cu1 176.5(4) 9_676 . ?
N1 C1 Cu1 169.1(3) . . ?
N3 C2 H2A 108.4 . . ?
N3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 N3 115.4(2) . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

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 Cu1 C1 N1 0.0 3_656 . . . ?
N2 Cu1 C1 N1 180.0 . . . . ?
C2 N3 C2 C3 179.1(3) 2_665 . . . ?
C2 N3 C2 C3 57.9(2) 7_545 . . . ?
C2 N3 C2 C3 -59.8(2) 8_455 . . . ?

_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_230413_teacu_400k
_database_code_depnum_ccdc_archive 'CCDC 2337203'
loop_
_audit_author_name
_audit_author_address
'Ryo Ohtani'
;Kyushu university
Japan
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-04-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C4 Cu4 N8), C8 H20 N'
_chemical_formula_sum            'C10 H20 Cu2 N5'
_chemical_formula_weight         337.39
_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'
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      orthorhombic
_space_group_IT_number           72
_space_group_name_H-M_alt        'I b a m'
_space_group_name_Hall           '-I 2 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1, y+1, -z+1/2'
'x+1, -y+1, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'x, -y, z+1/2'
'-x, y, z+1/2'

_cell_length_a                   14.7531(7)
_cell_length_b                   8.2731(4)
_cell_length_c                   12.6466(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1543.57(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3729
_cell_measurement_temperature    400.0
_cell_measurement_theta_max      23.49
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.783
_shelx_estimated_absorpt_T_min   0.494
_exptl_absorpt_coefficient_mu    2.743
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1059 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.7808.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             692
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -1.00 0.00 0.0600
-1.00 -1.00 1.00 0.0780
0.00 -1.00 0.00 0.0670
1.00 0.00 1.00 0.1050
-1.00 0.00 0.00 0.0130
1.00 0.00 0.00 0.0470
0.00 0.00 -1.00 0.1360
1.00 1.00 -1.00 0.0940
0.00 1.00 0.00 0.0130

_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.094
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5704
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.671
_diffrn_reflns_theta_min         2.761
_diffrn_ambient_temperature      400.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                619
_reflns_number_total             757
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.063
_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)+(0.0416P)²+1.0344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0997
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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 0.34096(4) 0.09454(7) 0.500000 0.1032(3) Uani 1 2 d S T P . .
C1 C 0.2895(3) 0.3028(5) 0.500000 0.0964(12) Uani 1 2 d S T P . .
N1 N 0.2470(3) 0.4184(5) 0.500000 0.1181(14) Uani 1 2 d S T P . .
N3 N 0.500000 0.500000 0.250000 0.0944(14) Uani 1 4 d S T P . .
N2 N 0.4633(3) 0.0249(6) 0.500000 0.1231(14) Uani 1 2 d S T P . .
C2 C 0.4423(3) 0.3963(5) 0.1774(3) 0.1409(16) Uani 1 1 d . . . . .
H2A H 0.406701 0.467074 0.132520 0.169 Uiso 1 1 calc R U . . .
H2B H 0.482288 0.334445 0.131867 0.169 Uiso 1 1 calc R U . . .
C3 C 0.3796(4) 0.2821(9) 0.2320(6) 0.240(4) Uani 1 1 d . . . . .
H3A H 0.343474 0.226493 0.180396 0.360 Uiso 1 1 calc R U . . .
H3B H 0.340781 0.341266 0.278981 0.360 Uiso 1 1 calc R U . . .
H3C H 0.414293 0.204888 0.271726 0.360 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 C1 1.883(5) . ?
Cu1 N1 1.951(5) 3_546 ?
Cu1 N2 1.894(4) . ?
C1 N1 1.144(6) . ?
N3 C2 1.517(4) 8_455 ?
N3 C2 1.517(4) 7_545 ?
N3 C2 1.517(4) 2_665 ?
N3 C2 1.517(4) . ?
N2 N2 1.160(7) 9_656 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.492(7) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 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
C1 Cu1 N1 114.51(18) . 3_546 ?
C1 Cu1 N2 131.48(19) . . ?
N2 Cu1 N1 114.00(17) . 3_546 ?
N1 C1 Cu1 170.6(4) . . ?
C1 N1 Cu1 171.5(4) . 3_556 ?
C2 N3 C2 105.5(4) 8_455 7_545 ?
C2 N3 C2 111.8(3) 7_545 2_665 ?
C2 N3 C2 111.2(3) 8_455 2_665 ?
C2 N3 C2 111.2(3) 7_545 . ?
C2 N3 C2 111.8(3) 8_455 . ?
C2 N3 C2 105.5(4) 2_665 . ?
N2 N2 Cu1 176.9(6) 9_656 . ?
N3 C2 H2A 108.5 . . ?
N3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 N3 115.2(4) . . ?
C3 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

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
C2 N3 C2 C3 -59.4(4) 8_455 . . . ?
C2 N3 C2 C3 58.2(4) 7_545 . . . ?
C2 N3 C2 C3 179.6(6) 2_665 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
