# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_tt_a
_database_code_depnum_ccdc_archive 'CCDC 2285106'
loop_
_audit_author_name
_audit_author_address
'Minyoung Yoon'
;Kyungpook National University
South Korea
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 Cu N4 O6'
_chemical_formula_weight         413.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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'
N N 0.0044 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0078 0.0044 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3370 0.9703 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.968(2)
_cell_length_b                   7.9070(16)
_cell_length_c                   21.463(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.99(3)
_cell_angle_gamma                90
_cell_volume                     1654.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    43366
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.901
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.610
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27826
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.665
_diffrn_reflns_theta_max         33.665
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8692
_reflns_number_gt                6913
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'PAL BL2D-SMDC Program (Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  WinGX
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0804P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8692
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.87137(2) 0.43696(2) 0.63794(2) 0.01196(5) Uani 1 1 d . . . . .
O1 O 0.83584(12) 0.20791(15) 0.59631(5) 0.0181(2) Uani 1 1 d . . . . .
N1 N 0.68539(12) 0.52875(16) 0.60465(5) 0.01318(18) Uani 1 1 d . . . . .
C1 C 0.56136(14) 0.44699(17) 0.59926(6) 0.0134(2) Uani 1 1 d . . . . .
H1 H 0.820(2) 0.882(3) 0.6014(11) 0.022(5) Uiso 1 1 d . . . . .
O2 O 0.87569(15) 0.10782(17) 0.50756(6) 0.0258(2) Uani 1 1 d . . . . .
N2 N 0.92948(11) 0.67974(15) 0.64391(5) 0.01179(18) Uani 1 1 d . . . . .
C2 C 0.55650(14) 0.2797(2) 0.62199(7) 0.0161(2) Uani 1 1 d . . . . .
H2 H 0.638(2) 0.223(2) 0.6406(10) 0.010(4) Uiso 1 1 d . . . . .
O3 O 0.95615(13) 0.35554(16) 0.54208(6) 0.0235(2) Uani 1 1 d . . . . .
N3 N 0.89093(12) 0.22239(16) 0.54752(6) 0.0156(2) Uani 1 1 d . . . . .
C3 C 0.43215(15) 0.1983(2) 0.61594(7) 0.0188(3) Uani 1 1 d . . . . .
H3 H 0.429(3) 0.086(3) 0.6326(12) 0.021(6) Uiso 1 1 d . . . . .
O4 O 1.03527(11) 0.35710(14) 0.70079(5) 0.01625(18) Uani 1 1 d . . . . .
N4 N 0.98130(13) 0.32496(16) 0.74959(6) 0.0158(2) Uani 1 1 d . . . . .
C4 C 0.30882(15) 0.2803(2) 0.58738(7) 0.0215(3) Uani 1 1 d . . . . .
H4 H 1.070(2) 0.663(3) 0.5907(10) 0.018(5) Uiso 1 1 d . . . . .
O5 O 0.85396(12) 0.34606(17) 0.74175(6) 0.0228(2) Uani 1 1 d . . . . .
C5 C 0.31096(15) 0.4430(2) 0.56565(8) 0.0198(3) Uani 1 1 d . . . . .
H5 H 0.231(3) 0.491(3) 0.5461(12) 0.026(6) Uiso 1 1 d . . . . .
O6 O 1.05364(14) 0.27661(17) 0.79952(5) 0.0252(2) Uani 1 1 d . . . . .
C6 C 0.43715(14) 0.5307(2) 0.57160(6) 0.0154(2) Uani 1 1 d . . . . .
H6 H 1.073(3) 0.952(3) 0.6127(13) 0.028(7) Uiso 1 1 d . . . . .
C7 C 0.44483(15) 0.7011(2) 0.55162(7) 0.0179(2) Uani 1 1 d . . . . .
H7 H 1.218(3) 0.879(3) 0.6333(11) 0.026(6) Uiso 1 1 d . . . . .
C8 C 0.56937(15) 0.77974(19) 0.55963(7) 0.0169(2) Uani 1 1 d . . . . .
H8 H 0.573(3) 0.891(3) 0.5479(12) 0.023(6) Uiso 1 1 d . . . . .
C9 C 0.68910(14) 0.68847(18) 0.58644(6) 0.0140(2) Uani 1 1 d . . . . .
H9 H 1.182(2) 0.872(3) 0.7399(12) 0.024(6) Uiso 1 1 d . . . . .
C10 C 0.82870(14) 0.76719(19) 0.59351(7) 0.0156(2) Uani 1 1 d . . . . .
H10 H 0.860(3) 0.753(3) 0.5522(12) 0.025(6) Uiso 1 1 d . . . . .
C11 C 0.92401(14) 0.74404(18) 0.70899(6) 0.0146(2) Uani 1 1 d . . . . .
H11 H 0.972(2) 0.948(2) 0.7655(11) 0.011(5) Uiso 1 1 d . . . . .
C12 C 0.97755(17) 0.92412(19) 0.72143(7) 0.0172(2) Uani 1 1 d . . . . .
H12 H 0.918(3) 0.993(3) 0.6942(12) 0.022(5) Uiso 1 1 d . . . . .
C13 C 1.12305(16) 0.9401(2) 0.70949(8) 0.0191(3) Uani 1 1 d . . . . .
H13 H 1.154(2) 1.054(2) 0.7157(11) 0.012(5) Uiso 1 1 d . . . . .
C14 C 1.12546(15) 0.8795(2) 0.64230(7) 0.0175(2) Uani 1 1 d . . . . .
H14 H 0.360(2) 0.759(3) 0.5344(12) 0.025(6) Uiso 1 1 d . . . . .
C15 C 1.07190(14) 0.69929(19) 0.63224(7) 0.0154(2) Uani 1 1 d . . . . .
H15 H 1.127(3) 0.625(3) 0.6574(11) 0.024(6) Uiso 1 1 d . . . . .
H16 H 0.832(2) 0.734(3) 0.7178(11) 0.020(5) Uiso 1 1 d . . . . .
H17 H 0.983(2) 0.673(3) 0.7415(10) 0.015(5) Uiso 1 1 d . . . . .
H18 H 0.220(3) 0.228(3) 0.5863(13) 0.035(7) Uiso 1 1 d . . . . .


_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 1.9807(13) . ?
Cu1 O4 1.9930(12) . ?
Cu1 N2 2.0016(13) . ?
Cu1 O1 2.0180(12) . ?
Cu1 O5 2.3815(13) . ?
O1 N3 1.2847(16) . ?
N1 C9 1.3248(19) . ?
N1 C1 1.3786(18) . ?
C1 C2 1.414(2) . ?
C1 C6 1.420(2) . ?
O2 N3 1.2350(18) . ?
N2 C10 1.4853(18) . ?
N2 C11 1.4980(17) . ?
N2 C15 1.5000(18) . ?
C2 C3 1.379(2) . ?
C2 H2 0.94(2) . ?
O3 N3 1.2555(18) . ?
C3 C4 1.412(2) . ?
C3 H3 0.96(2) . ?
O4 N4 1.2981(16) . ?
N4 O6 1.2222(17) . ?
N4 O5 1.2564(17) . ?
C4 C5 1.370(3) . ?
C4 H18 0.98(3) . ?
C5 C6 1.419(2) . ?
C5 H5 0.91(3) . ?
C6 C7 1.421(2) . ?
C7 C8 1.367(2) . ?
C7 H14 0.97(2) . ?
C8 C9 1.411(2) . ?
C8 H8 0.92(2) . ?
C9 C10 1.503(2) . ?
C10 H1 0.93(3) . ?
C10 H10 1.01(3) . ?
C11 C12 1.525(2) . ?
C11 H16 0.97(2) . ?
C11 H17 0.99(2) . ?
C12 C13 1.530(2) . ?
C12 H11 0.98(2) . ?
C12 H12 0.92(3) . ?
C13 C14 1.525(2) . ?
C13 H9 0.95(2) . ?
C13 H13 0.948(19) . ?
C14 C15 1.521(2) . ?
C14 H6 0.93(3) . ?
C14 H7 0.98(3) . ?
C15 H4 0.93(2) . ?
C15 H15 0.90(2) . ?

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
N1 Cu1 O4 159.13(5) . . ?
N1 Cu1 N2 84.74(5) . . ?
O4 Cu1 N2 94.29(5) . . ?
N1 Cu1 O1 95.98(5) . . ?
O4 Cu1 O1 93.39(5) . . ?
N2 Cu1 O1 155.64(4) . . ?
N1 Cu1 O5 101.74(5) . . ?
O4 Cu1 O5 58.66(4) . . ?
N2 Cu1 O5 107.81(5) . . ?
O1 Cu1 O5 95.92(5) . . ?
N3 O1 Cu1 102.45(9) . . ?
C9 N1 C1 120.12(12) . . ?
C9 N1 Cu1 111.98(9) . . ?
C1 N1 Cu1 127.90(10) . . ?
N1 C1 C2 120.27(12) . . ?
N1 C1 C6 120.35(13) . . ?
C2 C1 C6 119.37(13) . . ?
C10 N2 C11 111.78(11) . . ?
C10 N2 C15 110.53(11) . . ?
C11 N2 C15 109.87(11) . . ?
C10 N2 Cu1 104.89(9) . . ?
C11 N2 Cu1 108.61(8) . . ?
C15 N2 Cu1 111.07(9) . . ?
C3 C2 C1 119.92(14) . . ?
C3 C2 H2 119.8(12) . . ?
C1 C2 H2 120.3(12) . . ?
O2 N3 O3 122.82(13) . . ?
O2 N3 O1 119.28(13) . . ?
O3 N3 O1 117.89(12) . . ?
C2 C3 C4 120.73(15) . . ?
C2 C3 H3 119.5(16) . . ?
C4 C3 H3 119.8(16) . . ?
N4 O4 Cu1 100.91(8) . . ?
O6 N4 O5 123.68(13) . . ?
O6 N4 O4 120.06(13) . . ?
O5 N4 O4 116.26(12) . . ?
C5 C4 C3 120.35(14) . . ?
C5 C4 H18 118.1(16) . . ?
C3 C4 H18 121.3(16) . . ?
N4 O5 Cu1 84.11(8) . . ?
C4 C5 C6 120.30(14) . . ?
C4 C5 H5 118.3(17) . . ?
C6 C5 H5 121.3(16) . . ?
C5 C6 C1 119.31(14) . . ?
C5 C6 C7 122.59(14) . . ?
C1 C6 C7 118.09(13) . . ?
C8 C7 C6 119.87(13) . . ?
C8 C7 H14 122.1(14) . . ?
C6 C7 H14 117.9(14) . . ?
C7 C8 C9 119.18(14) . . ?
C7 C8 H8 119.3(16) . . ?
C9 C8 H8 121.5(16) . . ?
N1 C9 C8 122.33(13) . . ?
N1 C9 C10 116.55(12) . . ?
C8 C9 C10 121.08(13) . . ?
N2 C10 C9 110.65(11) . . ?
N2 C10 H1 113.2(15) . . ?
C9 C10 H1 107.9(15) . . ?
N2 C10 H10 107.6(14) . . ?
C9 C10 H10 108.5(14) . . ?
H1 C10 H10 108.8(19) . . ?
N2 C11 C12 113.64(11) . . ?
N2 C11 H16 111.8(14) . . ?
C12 C11 H16 110.5(13) . . ?
N2 C11 H17 109.5(12) . . ?
C12 C11 H17 105.6(12) . . ?
H16 C11 H17 105.2(18) . . ?
C11 C12 C13 110.95(12) . . ?
C11 C12 H11 105.2(11) . . ?
C13 C12 H11 113.3(14) . . ?
C11 C12 H12 106.4(16) . . ?
C13 C12 H12 110.8(15) . . ?
H11 C12 H12 110(2) . . ?
C14 C13 C12 109.53(13) . . ?
C14 C13 H9 110.1(15) . . ?
C12 C13 H9 108.2(15) . . ?
C14 C13 H13 111.2(14) . . ?
C12 C13 H13 110.1(14) . . ?
H9 C13 H13 108(2) . . ?
C15 C14 C13 110.78(12) . . ?
C15 C14 H6 110.5(16) . . ?
C13 C14 H6 109.7(16) . . ?
C15 C14 H7 106.4(14) . . ?
C13 C14 H7 112.9(14) . . ?
H6 C14 H7 106(2) . . ?
N2 C15 C14 112.91(11) . . ?
N2 C15 H4 107.1(14) . . ?
C14 C15 H4 111.0(14) . . ?
N2 C15 H15 108.5(16) . . ?
C14 C15 H15 111.5(16) . . ?
H4 C15 H15 105(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 -176.38(12) . . . . ?
Cu1 N1 C1 C2 3.50(18) . . . . ?
C9 N1 C1 C6 2.79(19) . . . . ?
Cu1 N1 C1 C6 -177.33(10) . . . . ?
N1 C1 C2 C3 -179.46(13) . . . . ?
C6 C1 C2 C3 1.4(2) . . . . ?
Cu1 O1 N3 O2 -172.97(11) . . . . ?
Cu1 O1 N3 O3 5.62(14) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
Cu1 O4 N4 O6 -177.76(12) . . . . ?
Cu1 O4 N4 O5 2.44(14) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
O6 N4 O5 Cu1 178.20(14) . . . . ?
O4 N4 O5 Cu1 -2.02(12) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C1 1.1(2) . . . . ?
C4 C5 C6 C7 -178.06(14) . . . . ?
N1 C1 C6 C5 179.00(12) . . . . ?
C2 C1 C6 C5 -1.8(2) . . . . ?
N1 C1 C6 C7 -1.76(19) . . . . ?
C2 C1 C6 C7 177.42(12) . . . . ?
C5 C6 C7 C8 178.86(14) . . . . ?
C1 C6 C7 C8 -0.4(2) . . . . ?
C6 C7 C8 C9 1.4(2) . . . . ?
C1 N1 C9 C8 -1.7(2) . . . . ?
Cu1 N1 C9 C8 178.40(11) . . . . ?
C1 N1 C9 C10 -179.51(12) . . . . ?
Cu1 N1 C9 C10 0.59(15) . . . . ?
C7 C8 C9 N1 -0.4(2) . . . . ?
C7 C8 C9 C10 177.27(13) . . . . ?
C11 N2 C10 C9 -82.83(14) . . . . ?
C15 N2 C10 C9 154.46(12) . . . . ?
Cu1 N2 C10 C9 34.67(13) . . . . ?
N1 C9 C10 N2 -24.75(17) . . . . ?
C8 C9 C10 N2 157.40(12) . . . . ?
C10 N2 C11 C12 -69.58(15) . . . . ?
C15 N2 C11 C12 53.52(15) . . . . ?
Cu1 N2 C11 C12 175.18(10) . . . . ?
N2 C11 C12 C13 -54.98(16) . . . . ?
C11 C12 C13 C14 54.98(16) . . . . ?
C12 C13 C14 C15 -56.26(16) . . . . ?
C10 N2 C15 C14 69.30(15) . . . . ?
C11 N2 C15 C14 -54.52(15) . . . . ?
Cu1 N2 C15 C14 -174.70(9) . . . . ?
C13 C14 C15 N2 57.31(16) . . . . ?

_refine_diff_density_max         1.042
_refine_diff_density_min         -1.847
_refine_diff_density_rms         0.128

####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 2285107'
loop_
_audit_author_name
_audit_author_address
'Minyoung Yoon'
;Kyungpook National University
South Korea
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Cu N4 O7'
_chemical_formula_weight         415.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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'
N N 0.0044 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0078 0.0044 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3370 0.9703 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1870(14)
_cell_length_b                   8.2690(16)
_cell_length_c                   14.574(3)
_cell_angle_alpha                74.02(3)
_cell_angle_beta                 89.47(3)
_cell_angle_gamma                69.01(3)
_cell_volume                     773.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13621
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_F_000             426
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.967
_shelx_estimated_absorpt_T_min   0.830
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.610
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11409
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.333
_diffrn_reflns_theta_max         33.652
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.742
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.742
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.742
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             7198
_reflns_number_gt                6664
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'PAL BL2D-SMDC Program (Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  WinGX
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0776P)²+0.2567P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7198
_refine_ls_number_parameters     299
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.700
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu01 Cu 0.35847(2) 0.43579(2) 0.22241(2) 0.00659(5) Uani 1 1 d . U . . .
N01 N 0.74955(16) 0.32906(15) 0.26384(9) 0.01181(18) Uani 1 1 d . . . . .
N02 N 0.41500(15) 0.16323(14) 0.15421(9) 0.00929(16) Uani 1 1 d . . . . .
C011 C 0.17810(17) 0.71200(16) -0.02468(9) 0.00944(18) Uani 1 1 d . . . . .
N011 N 0.19725(14) 0.69987(12) 0.14883(7) 0.00627(14) Uani 1 1 d . U . . .
O011 O -0.03371(14) 0.76245(13) -0.02775(7) 0.01115(16) Uani 1 1 d . . . . .
C012 C 0.25892(17) 0.76909(15) 0.05207(9) 0.00881(17) Uani 1 1 d . . . . .
N012 N 0.27559(15) 0.52356(13) 0.33467(8) 0.00768(15) Uani 1 1 d . . . . .
C013 C -0.02359(16) 0.74357(15) 0.14109(9) 0.00860(17) Uani 1 1 d . . . . .
C014 C -0.08611(18) 0.67923(17) 0.06276(10) 0.01102(19) Uani 1 1 d . . . . .
C015 C 0.24703(18) 0.79477(15) 0.21274(9) 0.00846(17) Uani 1 1 d . U . . .
C016 C 0.24232(17) 0.69887(15) 0.31579(9) 0.00784(17) Uani 1 1 d . . . . .
H17 H 0.185(4) 0.906(4) 0.3732(19) 0.018(6) Uiso 1 1 d . . . . .
C017 C 0.21104(19) 0.78753(16) 0.38774(10) 0.01059(19) Uani 1 1 d . . . . .
H18 H 0.205(4) 0.732(3) 0.5324(18) 0.013(5) Uiso 1 1 d . . . . .
C018 C 0.21523(19) 0.68899(17) 0.48088(10) 0.01090(19) Uani 1 1 d . . . . .
C019 C 0.24439(17) 0.50322(16) 0.50299(9) 0.00868(17) Uani 1 1 d . . . . .
H20 H 0.231(4) 0.440(3) 0.6468(19) 0.016(6) Uiso 1 1 d . . . . .
C020 C 0.24385(19) 0.39468(18) 0.59725(10) 0.0118(2) Uani 1 1 d . . . . .
H21 H 0.271(4) 0.145(3) 0.6731(18) 0.010(5) Uiso 1 1 d . . . . .
C021 C 0.26881(19) 0.21622(17) 0.61391(10) 0.0122(2) Uani 1 1 d . . . . .
H22 H 0.308(4) 0.010(4) 0.545(2) 0.023(6) Uiso 1 1 d . . . . .
C022 C 0.29157(19) 0.13966(16) 0.53698(10) 0.0122(2) Uani 1 1 d . . . . .
H23 H 0.308(4) 0.194(4) 0.398(2) 0.020(6) Uiso 1 1 d . . . . .
C023 C 0.29429(18) 0.24024(15) 0.44478(10) 0.01020(18) Uani 1 1 d . . . . .
C024 C 0.27256(16) 0.42332(14) 0.42677(9) 0.00718(16) Uani 1 1 d . . . . .
O01A O 0.92855(17) 0.25476(19) 0.29195(11) 0.0245(3) Uani 1 1 d . . . . .
O02A O 0.34217(16) 0.13190(15) 0.23171(8) 0.01487(18) Uani 1 1 d . . . . .
H11A H 0.198(4) 0.774(3) -0.0842(19) 0.017(6) Uiso 1 1 d . . . . .
H12A H 0.397(4) 0.725(3) 0.0559(18) 0.011(5) Uiso 1 1 d . . . . .
H13A H -0.058(3) 0.686(3) 0.2016(15) 0.001(4) Uiso 1 1 d . . . . .
H14A H -0.227(4) 0.713(4) 0.054(2) 0.019(6) Uiso 1 1 d . . . . .
H15A H 0.163(3) 0.910(3) 0.2017(17) 0.009(5) Uiso 1 1 d . . . . .
O01B O 0.62887(15) 0.24571(13) 0.29363(8) 0.01282(16) Uani 1 1 d . . . . .
O02B O 0.49150(16) 0.05100(14) 0.11141(9) 0.01551(19) Uani 1 1 d . . . . .
H11B H 0.241(3) 0.588(3) -0.0167(15) 0.004(4) Uiso 1 1 d . . . . .
H12B H 0.217(4) 0.897(3) 0.0382(19) 0.014(5) Uiso 1 1 d . . . . .
H13B H -0.094(3) 0.885(3) 0.1243(16) 0.005(4) Uiso 1 1 d . . . . .
H14B H -0.015(4) 0.545(4) 0.083(2) 0.018(6) Uiso 1 1 d . . . . .
H15B H 0.371(4) 0.788(3) 0.2044(19) 0.015(6) Uiso 1 1 d . . . . .
O01C O 0.67466(16) 0.48689(14) 0.20832(8) 0.01379(17) Uani 1 1 d . . . . .
O02C O 0.41034(15) 0.32828(12) 0.11713(8) 0.01117(15) Uani 1 1 d . 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
Cu01 O02C 1.9459(11) . ?
Cu01 N012 1.9708(12) . ?
Cu01 N011 2.0451(13) . ?
Cu01 O01B 2.0678(14) . ?
N01 O01A 1.2269(15) . ?
N01 O01C 1.2535(16) . ?
N01 O01B 1.2932(16) . ?
N02 O02B 1.2245(15) . ?
N02 O02A 1.2418(16) . ?
N02 O02C 1.3106(14) . ?
C011 O011 1.4246(16) . ?
C011 C012 1.5201(17) . ?
C011 H11A 0.92(3) . ?
C011 H11B 0.93(2) . ?
N011 C015 1.4904(15) . ?
N011 C013 1.4942(15) . ?
N011 C012 1.4960(17) . ?
O011 C014 1.4255(18) . ?
C012 H12A 0.92(2) . ?
C012 H12B 0.95(3) . ?
N012 C016 1.3295(15) . ?
N012 C024 1.3745(17) . ?
C013 C014 1.5177(18) . ?
C013 H13A 0.96(2) . ?
C013 H13B 1.05(2) . ?
C014 H14A 0.95(3) . ?
C014 H14B 1.00(3) . ?
C015 C016 1.4994(18) . ?
C015 H15A 0.90(2) . ?
C015 H15B 0.89(3) . ?
C016 C017 1.4101(18) . ?
C017 C018 1.372(2) . ?
C017 H17 0.89(3) . ?
C018 C019 1.4162(17) . ?
C018 H18 0.91(2) . ?
C019 C024 1.4197(17) . ?
C019 C020 1.4199(19) . ?
C020 C021 1.3721(19) . ?
C020 H20 0.89(3) . ?
C021 C022 1.413(2) . ?
C021 H21 0.90(2) . ?
C022 C023 1.376(2) . ?
C022 H22 1.01(3) . ?
C023 C024 1.4134(16) . ?
C023 H23 0.85(3) . ?

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
O02C Cu01 N012 170.62(4) . . ?
O02C Cu01 N011 100.34(5) . . ?
N012 Cu01 N011 82.72(5) . . ?
O02C Cu01 O01B 88.77(5) . . ?
N012 Cu01 O01B 93.32(5) . . ?
N011 Cu01 O01B 147.52(4) . . ?
O01A N01 O01C 122.82(13) . . ?
O01A N01 O01B 119.89(13) . . ?
O01C N01 O01B 117.27(11) . . ?
O02B N02 O02A 124.64(12) . . ?
O02B N02 O02C 118.54(12) . . ?
O02A N02 O02C 116.82(11) . . ?
O011 C011 C012 111.72(10) . . ?
O011 C011 H11A 103.9(16) . . ?
C012 C011 H11A 110.0(16) . . ?
O011 C011 H11B 110.8(13) . . ?
C012 C011 H11B 111.5(13) . . ?
H11A C011 H11B 109(2) . . ?
C015 N011 C013 109.27(9) . . ?
C015 N011 C012 107.39(9) . . ?
C013 N011 C012 109.42(10) . . ?
C015 N011 Cu01 100.76(7) . . ?
C013 N011 Cu01 113.13(8) . . ?
C012 N011 Cu01 116.22(8) . . ?
C011 O011 C014 109.79(10) . . ?
N011 C012 C011 112.37(9) . . ?
N011 C012 H12A 108.3(15) . . ?
C011 C012 H12A 109.2(15) . . ?
N011 C012 H12B 107.3(16) . . ?
C011 C012 H12B 112.7(15) . . ?
H12A C012 H12B 107(2) . . ?
C016 N012 C024 119.88(11) . . ?
C016 N012 Cu01 111.70(9) . . ?
C024 N012 Cu01 127.95(8) . . ?
N011 C013 C014 111.04(10) . . ?
N011 C013 H13A 108.3(12) . . ?
C014 C013 H13A 110.1(12) . . ?
N011 C013 H13B 107.3(12) . . ?
C014 C013 H13B 109.4(12) . . ?
H13A C013 H13B 110.7(17) . . ?
O011 C014 C013 110.75(10) . . ?
O011 C014 H14A 105.0(17) . . ?
C013 C014 H14A 112.1(17) . . ?
O011 C014 H14B 111.9(16) . . ?
C013 C014 H14B 105.4(16) . . ?
H14A C014 H14B 112(2) . . ?
N011 C015 C016 110.41(9) . . ?
N011 C015 H15A 113.9(15) . . ?
C016 C015 H15A 107.2(15) . . ?
N011 C015 H15B 106.6(17) . . ?
C016 C015 H15B 107.9(17) . . ?
H15A C015 H15B 111(2) . . ?
N012 C016 C017 122.59(12) . . ?
N012 C016 C015 115.18(11) . . ?
C017 C016 C015 122.20(10) . . ?
C018 C017 C016 118.70(11) . . ?
C018 C017 H17 120.2(18) . . ?
C016 C017 H17 121.0(18) . . ?
C017 C018 C019 120.10(11) . . ?
C017 C018 H18 125.0(16) . . ?
C019 C018 H18 114.9(16) . . ?
C018 C019 C024 118.13(11) . . ?
C018 C019 C020 123.08(12) . . ?
C024 C019 C020 118.79(11) . . ?
C021 C020 C019 120.40(12) . . ?
C021 C020 H20 118.7(17) . . ?
C019 C020 H20 120.8(17) . . ?
C020 C021 C022 120.21(13) . . ?
C020 C021 H21 121.7(15) . . ?
C022 C021 H21 118.1(15) . . ?
C023 C022 C021 121.03(11) . . ?
C023 C022 H22 115.8(17) . . ?
C021 C022 H22 123.2(17) . . ?
C022 C023 C024 119.40(12) . . ?
C022 C023 H23 121.1(19) . . ?
C024 C023 H23 119.5(19) . . ?
N012 C024 C023 119.34(11) . . ?
N012 C024 C019 120.52(10) . . ?
C023 C024 C019 120.13(11) . . ?
N01 O01B Cu01 101.40(8) . . ?
N02 O02C Cu01 104.75(9) . . ?

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
C012 C011 O011 C014 -59.58(13) . . . . ?
C015 N011 C012 C011 -168.29(9) . . . . ?
C013 N011 C012 C011 -49.79(12) . . . . ?
Cu01 N011 C012 C011 79.85(10) . . . . ?
O011 C011 C012 N011 54.32(13) . . . . ?
C015 N011 C013 C014 169.40(10) . . . . ?
C012 N011 C013 C014 52.07(12) . . . . ?
Cu01 N011 C013 C014 -79.24(11) . . . . ?
C011 O011 C014 C013 62.20(12) . . . . ?
N011 C013 C014 O011 -59.36(13) . . . . ?
C013 N011 C015 C016 76.76(12) . . . . ?
C012 N011 C015 C016 -164.64(9) . . . . ?
Cu01 N011 C015 C016 -42.58(10) . . . . ?
C024 N012 C016 C017 2.57(17) . . . . ?
Cu01 N012 C016 C017 -170.18(9) . . . . ?
C024 N012 C016 C015 -179.34(10) . . . . ?
Cu01 N012 C016 C015 7.91(12) . . . . ?
N011 C015 C016 N012 25.44(14) . . . . ?
N011 C015 C016 C017 -156.46(11) . . . . ?
N012 C016 C017 C018 0.04(18) . . . . ?
C015 C016 C017 C018 -177.92(11) . . . . ?
C016 C017 C018 C019 -1.91(18) . . . . ?
C017 C018 C019 C024 1.19(17) . . . . ?
C017 C018 C019 C020 -177.88(12) . . . . ?
C018 C019 C020 C021 178.64(12) . . . . ?
C024 C019 C020 C021 -0.43(18) . . . . ?
C019 C020 C021 C022 -1.19(19) . . . . ?
C020 C021 C022 C023 1.66(19) . . . . ?
C021 C022 C023 C024 -0.44(19) . . . . ?
C016 N012 C024 C023 175.63(10) . . . . ?
Cu01 N012 C024 C023 -12.92(15) . . . . ?
C016 N012 C024 C019 -3.26(16) . . . . ?
Cu01 N012 C024 C019 168.19(8) . . . . ?
C022 C023 C024 N012 179.91(11) . . . . ?
C022 C023 C024 C019 -1.20(17) . . . . ?
C018 C019 C024 N012 1.39(16) . . . . ?
C020 C019 C024 N012 -179.49(10) . . . . ?
C018 C019 C024 C023 -177.49(11) . . . . ?
C020 C019 C024 C023 1.63(16) . . . . ?
O01A N01 O01B Cu01 -179.87(11) . . . . ?
O01C N01 O01B Cu01 1.87(13) . . . . ?
O02B N02 O02C Cu01 -162.73(10) . . . . ?
O02A N02 O02C Cu01 16.56(12) . . . . ?

_refine_diff_density_max         1.132
_refine_diff_density_min         -1.463
_refine_diff_density_rms         0.131



# start Validation Reply Form
_vrf_PLAT029_a_a                 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.951 Why?
RESPONSE: This alert was generated because of the data collection of one axis rotation 
(omega scan) of a low symmetry crystal, which is the restriction of a synchrotron 
instrument. To avoid the structure issue, the molecular structure 
was also confirmed by IR data.
;
_vrf_PLAT213_a_a                 
;
PROBLEM: Atom Cu01 has ADP max/min Ratio ..... 3.7 prolat
RESPONSE: Because of the significant distortion of Cu metal center and 
significant distortion on Cu metal center (distorted square planar 
or distorted octahedron) geometry, non-negligible disorder occurred.
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2285108'
loop_
_audit_author_name
_audit_author_address
'Hyosun Lee'
;Kyungpook National University
South Korea
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H32 Cl4 Cu2 N4'
_chemical_formula_sum            'C22 H32 Cl4 Cu2 N4'
_chemical_formula_weight         621.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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'
N N 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1230 0.1251 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3383 1.0251 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.682(2)
_cell_length_b                   7.1300(14)
_cell_length_c                   16.493(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.03(3)
_cell_angle_gamma                90
_cell_volume                     1236.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    31318
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    1.553
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'HKL3000sm Scalepack'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12134
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.716
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3481
_reflns_number_gt                2595
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'PAL BL2D-SMDC Program (Shin et. al, 2016)'
_computing_cell_refinement       HKL3000sm
_computing_data_reduction        HKL3000sm
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  WinGX
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3481
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.16622(3) 0.51394(4) 0.54373(2) 0.00868(10) Uani 1 1 d . . . . .
Cl1 Cl 0.03224(6) 0.26864(9) 0.49645(4) 0.01228(15) Uani 1 1 d . . . . .
Cl2 Cl 0.27531(7) 0.50015(9) 0.43855(4) 0.01615(16) Uani 1 1 d . . . . .
N1 N 0.1474(2) 0.4629(3) 0.66202(13) 0.0101(4) Uani 1 1 d . . . . .
N2 N 0.27593(19) 0.7345(3) 0.60161(12) 0.0077(4) Uani 1 1 d . . . . .
C1 C 0.1150(3) 0.2997(4) 0.69389(16) 0.0143(6) Uani 1 1 d . . . . .
H1 H 0.089951 0.197148 0.657934 0.017 Uiso 1 1 calc R U . . .
C2 C 0.1170(3) 0.2768(4) 0.77751(17) 0.0169(6) Uani 1 1 d . . . . .
H2 H 0.095743 0.159232 0.798598 0.020 Uiso 1 1 calc R U . . .
C3 C 0.1500(3) 0.4260(5) 0.82970(17) 0.0181(6) Uani 1 1 d . . . . .
H3 H 0.151646 0.412739 0.887190 0.022 Uiso 1 1 calc R U . . .
C4 C 0.1808(3) 0.5962(4) 0.79741(16) 0.0149(6) Uani 1 1 d . . . . .
H4 H 0.202259 0.702030 0.832063 0.018 Uiso 1 1 calc R U . . .
C5 C 0.1796(2) 0.6082(4) 0.71308(16) 0.0095(5) Uani 1 1 d . . . . .
C6 C 0.2109(2) 0.7838(4) 0.67145(15) 0.0109(5) Uani 1 1 d . . . . .
H6A H 0.132035 0.854529 0.650857 0.013 Uiso 1 1 calc R U . . .
H6B H 0.267034 0.864148 0.711188 0.013 Uiso 1 1 calc R U . . .
C7 C 0.4078(2) 0.6617(4) 0.63130(16) 0.0119(5) Uani 1 1 d . . . . .
H7A H 0.443136 0.614188 0.583563 0.014 Uiso 1 1 calc R U . . .
H7B H 0.403285 0.554983 0.669083 0.014 Uiso 1 1 calc R U . . .
C8 C 0.4981(3) 0.8106(4) 0.67605(17) 0.0173(6) Uani 1 1 d . . . . .
H8A H 0.469083 0.847969 0.727545 0.021 Uiso 1 1 calc R U . . .
H8B H 0.584649 0.757330 0.690826 0.021 Uiso 1 1 calc R U . . .
C9 C 0.5019(3) 0.9828(4) 0.6214(2) 0.0192(6) Uani 1 1 d . . . . .
H9A H 0.543272 0.949487 0.574154 0.023 Uiso 1 1 calc R U . . .
H9B H 0.553086 1.082498 0.653309 0.023 Uiso 1 1 calc R U . . .
C10 C 0.3676(3) 1.0567(4) 0.58963(18) 0.0160(6) Uani 1 1 d . . . . .
H10A H 0.330866 1.107291 0.636250 0.019 Uiso 1 1 calc R U . . .
H10B H 0.371837 1.160015 0.550115 0.019 Uiso 1 1 calc R U . . .
C11 C 0.2823(3) 0.9013(4) 0.54747(16) 0.0119(5) Uani 1 1 d . . . . .
H11A H 0.195385 0.951628 0.529948 0.014 Uiso 1 1 calc R U . . .
H11B H 0.314362 0.860953 0.497424 0.014 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 2.029(2) . ?
Cu1 N2 2.090(2) . ?
Cu1 Cl2 2.2541(9) . ?
Cu1 Cl1 2.3079(8) . ?
Cu1 Cl1 2.6168(8) 3_566 ?
N1 C5 1.342(3) . ?
N1 C1 1.347(3) . ?
N2 C6 1.487(3) . ?
N2 C11 1.496(3) . ?
N2 C7 1.501(3) . ?
C1 C2 1.385(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.375(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.493(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.534(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.527(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.533(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.524(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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
N1 Cu1 N2 80.64(9) . . ?
N1 Cu1 Cl2 152.05(7) . . ?
N2 Cu1 Cl2 93.46(6) . . ?
N1 Cu1 Cl1 91.69(7) . . ?
N2 Cu1 Cl1 171.86(6) . . ?
Cl2 Cu1 Cl1 94.60(3) . . ?
N1 Cu1 Cl1 97.95(7) . 3_566 ?
N2 Cu1 Cl1 92.01(6) . 3_566 ?
Cl2 Cu1 Cl1 109.61(3) . 3_566 ?
Cl1 Cu1 Cl1 86.33(3) . 3_566 ?
Cu1 Cl1 Cu1 93.67(3) . 3_566 ?
C5 N1 C1 118.5(2) . . ?
C5 N1 Cu1 114.04(18) . . ?
C1 N1 Cu1 127.28(19) . . ?
C6 N2 C11 110.5(2) . . ?
C6 N2 C7 111.56(19) . . ?
C11 N2 C7 109.4(2) . . ?
C6 N2 Cu1 103.38(15) . . ?
C11 N2 Cu1 113.93(15) . . ?
C7 N2 Cu1 107.98(16) . . ?
N1 C1 C2 122.0(3) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 122.5(3) . . ?
N1 C5 C6 114.4(2) . . ?
C4 C5 C6 123.2(2) . . ?
N2 C6 C5 109.3(2) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 C8 113.1(2) . . ?
N2 C7 H7A 108.9 . . ?
C8 C7 H7A 109.0 . . ?
N2 C7 H7B 108.9 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 110.6(2) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 111.0(2) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 110.9(2) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C10 113.0(2) . . ?
N2 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
N2 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?

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
C5 N1 C1 C2 -1.6(4) . . . . ?
Cu1 N1 C1 C2 173.7(2) . . . . ?
N1 C1 C2 C3 1.6(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C1 N1 C5 C4 0.1(4) . . . . ?
Cu1 N1 C5 C4 -175.8(2) . . . . ?
C1 N1 C5 C6 -178.6(2) . . . . ?
Cu1 N1 C5 C6 5.5(3) . . . . ?
C3 C4 C5 N1 1.3(4) . . . . ?
C3 C4 C5 C6 179.9(2) . . . . ?
C11 N2 C6 C5 167.23(19) . . . . ?
C7 N2 C6 C5 -70.8(3) . . . . ?
Cu1 N2 C6 C5 45.0(2) . . . . ?
N1 C5 C6 N2 -35.3(3) . . . . ?
C4 C5 C6 N2 146.0(2) . . . . ?
C6 N2 C7 C8 -66.5(3) . . . . ?
C11 N2 C7 C8 56.1(3) . . . . ?
Cu1 N2 C7 C8 -179.40(17) . . . . ?
N2 C7 C8 C9 -55.4(3) . . . . ?
C7 C8 C9 C10 53.0(3) . . . . ?
C8 C9 C10 C11 -53.5(3) . . . . ?
C6 N2 C11 C10 66.8(3) . . . . ?
C7 N2 C11 C10 -56.4(3) . . . . ?
Cu1 N2 C11 C10 -177.35(18) . . . . ?
C9 C10 C11 N2 56.1(3) . . . . ?

_refine_diff_density_max         1.012
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.137

