# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_Complex1
_database_code_depnum_ccdc_archive 'CCDC 2290988'
loop_
_audit_author_name
_audit_author_address
'Thammarat Aree'
;Chulalongkorn University
Thailand
;
_audit_update_record             
;
2023-08-27 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 Cl2 Cu N4 O10'
_chemical_formula_sum            'C18 H20 Cl2 Cu N4 O10'
_chemical_formula_weight         586.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.1215(11)
_cell_length_b                   20.904(4)
_cell_length_c                   10.697(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.860(6)
_cell_angle_gamma                90
_cell_volume                     1120.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    406
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      21.83

_exptl_crystal_description       rod
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_F_000             598
_exptl_transmission_factor_min   0.6789
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.277
_shelx_estimated_absorpt_T_min   0.770
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16291
_diffrn_reflns_av_unetI/netI     0.0942
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.176
_diffrn_reflns_theta_max         30.551
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3419
_reflns_number_gt                1902
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0407P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3419
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_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 0.000000 0.500000 1.000000 0.02756(16) Uani 1 2 d S . P . .
Cl1 Cl 0.2693(2) 0.30665(4) 0.85185(8) 0.0494(3) Uani 1 1 d . . . . .
O1 O -0.2831(4) 0.55966(10) 0.83345(19) 0.0381(5) Uani 1 1 d . . . . .
H1 H -0.235294 0.535743 0.781708 0.057 Uiso 1 1 d . U . . .
O2 O 0.1824(4) 0.45051(10) 0.87488(18) 0.0341(5) Uani 1 1 d . . . . .
O3 O -0.0836(5) 0.47719(12) 0.6891(2) 0.0522(7) Uani 1 1 d . . . . .
O4 O 0.8908(6) 0.25768(13) 0.5357(2) 0.0628(8) Uani 1 1 d . . . . .
O5 O 0.7858(7) 0.32193(14) 0.3778(3) 0.0769(10) Uani 1 1 d . . . . .
N1 N 0.2305(5) 0.57554(12) 0.9926(2) 0.0350(6) Uani 1 1 d . . . . .
H1A H 0.220818 0.601705 1.057075 0.042 Uiso 1 1 calc R U . . .
H1B H 0.399174 0.562783 1.001576 0.042 Uiso 1 1 calc R U . . .
N2 N 0.7695(6) 0.30331(14) 0.4838(3) 0.0421(7) Uani 1 1 d . . . . .
C1 C -0.1444(7) 0.61903(15) 0.8372(3) 0.0399(8) Uani 1 1 d . . . . .
H1C H -0.199596 0.646927 0.899457 0.048 Uiso 1 1 calc R U . . .
H1D H -0.192227 0.639562 0.754316 0.048 Uiso 1 1 calc R U . . .
C2 C 0.1514(6) 0.61049(15) 0.8712(3) 0.0381(8) Uani 1 1 d . . . . .
H2A H 0.210167 0.587017 0.803797 0.046 Uiso 1 1 calc R U . . .
H2B H 0.237364 0.652057 0.878763 0.046 Uiso 1 1 calc R U . . .
C3 C 0.1044(6) 0.44727(14) 0.7543(3) 0.0326(7) Uani 1 1 d . . . . .
C4 C 0.2651(6) 0.40525(13) 0.6831(3) 0.0291(7) Uani 1 1 d . . . . .
C5 C 0.3666(6) 0.34493(14) 0.7246(3) 0.0310(7) Uani 1 1 d . . . . .
C6 C 0.5306(7) 0.31138(14) 0.6608(3) 0.0343(7) Uani 1 1 d . . . . .
H6 H 0.599779 0.271731 0.690097 0.041 Uiso 1 1 calc R U . . .
C7 C 0.5892(6) 0.33867(14) 0.5515(3) 0.0318(7) Uani 1 1 d . . . . .
C8 C 0.4842(7) 0.39601(15) 0.5034(3) 0.0368(8) Uani 1 1 d . . . . .
H8 H 0.520110 0.412292 0.427762 0.044 Uiso 1 1 calc R U . . .
C9 C 0.3237(7) 0.42887(15) 0.5702(3) 0.0367(8) Uani 1 1 d . . . . .
H9 H 0.252285 0.468019 0.538952 0.044 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 1.983(2) . ?
Cu1 N1 1.983(2) 3_567 ?
Cu1 O2 2.061(2) . ?
Cu1 O2 2.061(2) 3_567 ?
Cu1 O1 2.402(2) . ?
Cu1 O1 2.402(2) 3_567 ?
Cl1 C5 1.738(3) . ?
O1 C1 1.427(4) . ?
O1 H1 0.8199 . ?
O2 C3 1.271(3) . ?
O3 C3 1.236(4) . ?
O4 N2 1.210(3) . ?
O5 N2 1.217(3) . ?
N1 C2 1.472(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N2 C7 1.483(4) . ?
C1 C2 1.494(5) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.512(4) . ?
C4 C9 1.393(4) . ?
C4 C5 1.401(4) . ?
C5 C6 1.377(4) . ?
C6 C7 1.389(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.370(4) . ?
C8 C9 1.378(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 180.00(12) . 3_567 ?
N1 Cu1 O2 91.18(9) . . ?
N1 Cu1 O2 88.83(9) 3_567 . ?
N1 Cu1 O2 88.82(9) . 3_567 ?
N1 Cu1 O2 91.18(9) 3_567 3_567 ?
O2 Cu1 O2 180.00(7) . 3_567 ?
N1 Cu1 O1 80.24(9) . . ?
N1 Cu1 O1 99.76(9) 3_567 . ?
O2 Cu1 O1 93.67(7) . . ?
O2 Cu1 O1 86.33(7) 3_567 . ?
N1 Cu1 O1 99.76(9) . 3_567 ?
N1 Cu1 O1 80.24(9) 3_567 3_567 ?
O2 Cu1 O1 86.33(7) . 3_567 ?
O2 Cu1 O1 93.67(7) 3_567 3_567 ?
O1 Cu1 O1 180.00(8) . 3_567 ?
C1 O1 Cu1 102.10(17) . . ?
C1 O1 H1 109.5 . . ?
Cu1 O1 H1 88.0 . . ?
C3 O2 Cu1 126.6(2) . . ?
C2 N1 Cu1 111.86(19) . . ?
C2 N1 H1A 109.2 . . ?
Cu1 N1 H1A 109.2 . . ?
C2 N1 H1B 109.2 . . ?
Cu1 N1 H1B 109.2 . . ?
H1A N1 H1B 107.9 . . ?
O4 N2 O5 123.6(3) . . ?
O4 N2 C7 118.8(3) . . ?
O5 N2 C7 117.7(3) . . ?
O1 C1 C2 112.1(3) . . ?
O1 C1 H1C 109.2 . . ?
C2 C1 H1C 109.2 . . ?
O1 C1 H1D 109.2 . . ?
C2 C1 H1D 109.2 . . ?
H1C C1 H1D 107.9 . . ?
N1 C2 C1 110.8(3) . . ?
N1 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
O3 C3 O2 126.3(3) . . ?
O3 C3 C4 116.8(3) . . ?
O2 C3 C4 116.9(3) . . ?
C9 C4 C5 117.5(3) . . ?
C9 C4 C3 117.9(3) . . ?
C5 C4 C3 124.6(3) . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 Cl1 117.1(2) . . ?
C4 C5 Cl1 121.0(2) . . ?
C5 C6 C7 117.9(3) . . ?
C5 C6 H6 121.1 . . ?
C7 C6 H6 121.1 . . ?
C8 C7 C6 122.7(3) . . ?
C8 C7 N2 119.2(3) . . ?
C6 C7 N2 118.1(3) . . ?
C7 C8 C9 118.1(3) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C8 C9 C4 122.0(3) . . ?
C8 C9 H9 119.0 . . ?
C4 C9 H9 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C2 34.2(3) . . . . ?
Cu1 N1 C2 C1 45.3(3) . . . . ?
O1 C1 C2 N1 -55.0(4) . . . . ?
Cu1 O2 C3 O3 6.0(5) . . . . ?
Cu1 O2 C3 C4 -177.21(18) . . . . ?
O3 C3 C4 C9 40.8(4) . . . . ?
O2 C3 C4 C9 -136.3(3) . . . . ?
O3 C3 C4 C5 -141.3(3) . . . . ?
O2 C3 C4 C5 41.6(4) . . . . ?
C9 C4 C5 C6 3.5(5) . . . . ?
C3 C4 C5 C6 -174.4(3) . . . . ?
C9 C4 C5 Cl1 -171.4(2) . . . . ?
C3 C4 C5 Cl1 10.7(4) . . . . ?
C4 C5 C6 C7 -1.3(5) . . . . ?
Cl1 C5 C6 C7 173.9(2) . . . . ?
C5 C6 C7 C8 -2.1(5) . . . . ?
C5 C6 C7 N2 178.9(3) . . . . ?
O4 N2 C7 C8 169.6(3) . . . . ?
O5 N2 C7 C8 -10.7(5) . . . . ?
O4 N2 C7 C6 -11.4(5) . . . . ?
O5 N2 C7 C6 168.3(3) . . . . ?
C6 C7 C8 C9 3.0(5) . . . . ?
N2 C7 C8 C9 -178.1(3) . . . . ?
C7 C8 C9 C4 -0.5(5) . . . . ?
C5 C4 C9 C8 -2.6(5) . . . . ?
C3 C4 C9 C8 175.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.82 1.84 2.655(3) 170.1 . yes
N1 H1B O2 0.89 2.29 3.097(3) 150.5 3_667 yes
C1 H1C Cl1 0.97 2.92 3.842(3) 158.8 3_567 yes
C2 H2B O4 0.97 2.53 3.255(4) 131.7 2_656 yes

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_Complex3
_database_code_depnum_ccdc_archive 'CCDC 2290990'
loop_
_audit_author_name
_audit_author_address
'Thammarat Aree'
;Chulalongkorn University
Thailand
;
_audit_update_record             
;
2023-08-27 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H30 Cl2 Cu N6 O10'
_chemical_formula_sum            'C22 H30 Cl2 Cu N6 O10'
_chemical_formula_weight         672.96

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.6447(15)
_cell_length_b                   6.2469(11)
_cell_length_c                   19.4239(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.353(4)
_cell_angle_gamma                90
_cell_volume                     1401.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    795
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      21.40

_exptl_crystal_description       rod
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_F_000             694
_exptl_transmission_factor_min   0.6029
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    1.035
_shelx_estimated_absorpt_T_min   0.761
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17070
_diffrn_reflns_av_unetI/netI     0.1038
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.114
_diffrn_reflns_theta_max         30.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4261
_reflns_number_gt                2401
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0757P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4261
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1731
_refine_ls_wR_factor_gt          0.1450
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 1.000000 0.000000 0.500000 0.02696(19) Uani 1 2 d S . P . .
Cl1 Cl 0.59886(11) 0.2090(2) 0.54418(7) 0.0635(4) Uani 1 1 d . . . . .
O1 O 0.9150(3) 0.3478(6) 0.28861(17) 0.0563(9) Uani 1 1 d . . . . .
H1 H 0.898849 0.372574 0.247040 0.08(2) Uiso 1 1 calc R . . . .
O2 O 0.8948(3) 0.3104(4) 0.55148(14) 0.0398(7) Uani 1 1 d . . . . .
O3 O 0.8779(3) 0.1159(4) 0.64575(14) 0.0417(7) Uani 1 1 d . . . . .
O4 O 0.4269(3) 0.8836(6) 0.6501(2) 0.0668(11) Uani 1 1 d . . . . .
O5 O 0.5564(3) 1.0146(6) 0.7265(2) 0.0797(13) Uani 1 1 d . . . . .
N1 N 0.9096(3) 0.0394(4) 0.40402(15) 0.0267(7) Uani 1 1 d . . . . .
H1A H 0.965375 0.032717 0.370348 0.032 Uiso 1 1 calc R U . . .
N2 N 0.8713(3) -0.2038(4) 0.51704(15) 0.0306(7) Uani 1 1 d . . . . .
H2A H 0.898993 -0.336456 0.522311 0.037 Uiso 1 1 calc R U . . .
H2B H 0.842686 -0.166865 0.555683 0.037 Uiso 1 1 calc R U . . .
N3 N 0.5232(3) 0.8841(6) 0.6814(2) 0.0465(9) Uani 1 1 d . . . . .
C1 C 0.7785(3) -0.1952(6) 0.4569(2) 0.0366(9) Uani 1 1 d . . . . .
H1B H 0.723339 -0.083624 0.464026 0.044 Uiso 1 1 calc R U . . .
H1C H 0.737665 -0.330752 0.452101 0.044 Uiso 1 1 calc R U . . .
C2 C 0.8337(3) -0.1491(5) 0.39211(19) 0.0320(9) Uani 1 1 d . . . . .
H2C H 0.878535 -0.271947 0.380654 0.038 Uiso 1 1 calc R U . . .
H2D H 0.774029 -0.122150 0.353461 0.038 Uiso 1 1 calc R U . . .
C3 C 0.8479(3) 0.2461(5) 0.39351(18) 0.0284(8) Uani 1 1 d . . . . .
H3A H 0.897209 0.358716 0.415266 0.034 Uiso 1 1 calc R U . . .
H3B H 0.778762 0.240734 0.416478 0.034 Uiso 1 1 calc R U . . .
C4 C 0.8135(3) 0.3022(6) 0.3174(2) 0.0350(9) Uani 1 1 d . . . . .
H4A H 0.773078 0.182950 0.293221 0.042 Uiso 1 1 calc R U . . .
H4B H 0.762528 0.425609 0.313340 0.042 Uiso 1 1 calc R U . . .
C5 C 0.8539(3) 0.2726(5) 0.60567(19) 0.0291(8) Uani 1 1 d . . . . .
C6 C 0.7642(3) 0.4269(5) 0.62689(17) 0.0248(7) Uani 1 1 d . . . . .
C7 C 0.6484(3) 0.4155(6) 0.6012(2) 0.0332(9) Uani 1 1 d . . . . .
C8 C 0.5680(4) 0.5609(6) 0.6194(2) 0.0390(10) Uani 1 1 d . . . . .
H8 H 0.490111 0.549370 0.601923 0.047 Uiso 1 1 calc R U . . .
C9 C 0.6068(3) 0.7222(6) 0.6640(2) 0.0328(8) Uani 1 1 d . . . . .
C10 C 0.7207(3) 0.7409(6) 0.6918(2) 0.0333(8) Uani 1 1 d . . . . .
H10 H 0.744564 0.850294 0.722796 0.040 Uiso 1 1 calc R U . . .
C11 C 0.8000(3) 0.5922(6) 0.67249(19) 0.0320(8) Uani 1 1 d . . . . .
H11 H 0.877733 0.603863 0.690358 0.038 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 N2 2.025(3) 3_756 ?
Cu1 N2 2.025(3) . ?
Cu1 N1 2.035(3) 3_756 ?
Cu1 N1 2.035(3) . ?
Cl1 C7 1.749(4) . ?
O1 C4 1.400(5) . ?
O1 H1 0.8200 . ?
O2 C5 1.232(4) . ?
O3 C5 1.260(4) . ?
O4 N3 1.205(5) . ?
O5 N3 1.224(5) . ?
N1 C2 1.473(4) . ?
N1 C3 1.479(4) . ?
N1 H1A 0.9800 . ?
N2 C1 1.488(5) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N3 C9 1.473(5) . ?
C1 C2 1.512(6) . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 C4 1.522(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.517(5) . ?
C6 C7 1.379(5) . ?
C6 C11 1.389(5) . ?
C7 C8 1.382(5) . ?
C8 C9 1.367(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(5) . ?
C10 C11 1.394(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N2 180.00(11) 3_756 . ?
N2 Cu1 N1 85.36(12) 3_756 3_756 ?
N2 Cu1 N1 94.65(12) . 3_756 ?
N2 Cu1 N1 94.64(12) 3_756 . ?
N2 Cu1 N1 85.36(12) . . ?
N1 Cu1 N1 180.0 3_756 . ?
C4 O1 H1 109.5 . . ?
C2 N1 C3 113.9(3) . . ?
C2 N1 Cu1 106.1(2) . . ?
C3 N1 Cu1 114.7(2) . . ?
C2 N1 H1A 107.3 . . ?
C3 N1 H1A 107.3 . . ?
Cu1 N1 H1A 107.3 . . ?
C1 N2 Cu1 109.1(2) . . ?
C1 N2 H2A 109.9 . . ?
Cu1 N2 H2A 109.9 . . ?
C1 N2 H2B 109.9 . . ?
Cu1 N2 H2B 109.9 . . ?
H2A N2 H2B 108.3 . . ?
O4 N3 O5 123.5(4) . . ?
O4 N3 C9 118.9(4) . . ?
O5 N3 C9 117.7(4) . . ?
N2 C1 C2 108.5(3) . . ?
N2 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
N2 C1 H1C 110.0 . . ?
C2 C1 H1C 110.0 . . ?
H1B C1 H1C 108.4 . . ?
N1 C2 C1 109.4(3) . . ?
N1 C2 H2C 109.8 . . ?
C1 C2 H2C 109.8 . . ?
N1 C2 H2D 109.8 . . ?
C1 C2 H2D 109.8 . . ?
H2C C2 H2D 108.2 . . ?
N1 C3 C4 113.5(3) . . ?
N1 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
N1 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O1 C4 C3 107.7(3) . . ?
O1 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
O1 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
O2 C5 O3 126.7(3) . . ?
O2 C5 C6 117.7(3) . . ?
O3 C5 C6 115.6(3) . . ?
C7 C6 C11 117.9(3) . . ?
C7 C6 C5 123.0(3) . . ?
C11 C6 C5 119.0(3) . . ?
C6 C7 C8 122.5(3) . . ?
C6 C7 Cl1 119.7(3) . . ?
C8 C7 Cl1 117.9(3) . . ?
C9 C8 C7 117.8(4) . . ?
C9 C8 H8 121.1 . . ?
C7 C8 H8 121.1 . . ?
C8 C9 C10 122.5(3) . . ?
C8 C9 N3 118.5(4) . . ?
C10 C9 N3 119.1(3) . . ?
C9 C10 C11 118.5(3) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C6 C11 C10 120.8(4) . . ?
C6 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?

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
Cu1 N2 C1 C2 31.8(3) . . . . ?
C3 N1 C2 C1 -83.1(4) . . . . ?
Cu1 N1 C2 C1 44.0(3) . . . . ?
N2 C1 C2 N1 -51.2(4) . . . . ?
C2 N1 C3 C4 -75.6(4) . . . . ?
Cu1 N1 C3 C4 161.9(3) . . . . ?
N1 C3 C4 O1 -69.4(4) . . . . ?
O2 C5 C6 C7 83.4(5) . . . . ?
O3 C5 C6 C7 -95.9(4) . . . . ?
O2 C5 C6 C11 -94.4(4) . . . . ?
O3 C5 C6 C11 86.3(4) . . . . ?
C11 C6 C7 C8 -0.3(6) . . . . ?
C5 C6 C7 C8 -178.1(4) . . . . ?
C11 C6 C7 Cl1 -179.5(3) . . . . ?
C5 C6 C7 Cl1 2.7(5) . . . . ?
C6 C7 C8 C9 0.8(6) . . . . ?
Cl1 C7 C8 C9 180.0(3) . . . . ?
C7 C8 C9 C10 -1.4(6) . . . . ?
C7 C8 C9 N3 177.2(4) . . . . ?
O4 N3 C9 C8 -8.3(6) . . . . ?
O5 N3 C9 C8 172.8(4) . . . . ?
O4 N3 C9 C10 170.4(4) . . . . ?
O5 N3 C9 C10 -8.5(6) . . . . ?
C8 C9 C10 C11 1.5(6) . . . . ?
N3 C9 C10 C11 -177.2(3) . . . . ?
C7 C6 C11 C10 0.3(6) . . . . ?
C5 C6 C11 C10 178.2(3) . . . . ?
C9 C10 C11 C6 -0.9(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.82 1.95 2.763(4) 169.3 4_565 yes
N1 H1A O3 0.98 2.11 2.935(4) 141.2 3_756 yes
N2 H2A O2 0.89 2.28 3.112(4) 155.6 1_545 yes
N2 H2B O3 0.89 2.48 3.193(4) 137.1 . yes
C1 H1B Cl1 0.97 2.91 3.813(4) 156.0 . yes

_refine_diff_density_max         0.630
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_Complex2
_database_code_depnum_ccdc_archive 'CCDC 2290989'
loop_
_audit_author_name
_audit_author_address
'Thammarat Aree'
;Chulalongkorn University
Thailand
;
_audit_update_record             
;
2023-08-27 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H24 Cu N4 O2, 2(C7 H3 Cl N O4)'
_chemical_formula_sum            'C22 H30 Cl2 Cu N6 O10'
_chemical_formula_weight         672.96

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.2188(10)
_cell_length_b                   7.2384(11)
_cell_length_c                   13.1301(19)
_cell_angle_alpha                96.606(4)
_cell_angle_beta                 90.314(4)
_cell_angle_gamma                99.721(4)
_cell_volume                     671.52(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4275
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      27.06

_exptl_crystal_description       hexagon
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             347
_exptl_transmission_factor_min   0.6330
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    1.080
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19449
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.864
_diffrn_reflns_theta_max         30.612
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4126
_reflns_number_gt                2908
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0418P)²+0.2910P] 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         4126
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
Cu1 Cu 0.000000 0.500000 0.500000 0.02360(11) Uani 1 2 d S . P . .
O1 O 0.1363(2) 0.8312(2) 0.55104(11) 0.0299(3) Uani 1 1 d . . . . .
H1 H 0.216453 0.838048 0.596416 0.045 Uiso 1 1 calc R U . . .
O2 O 0.5795(3) 0.6908(3) 0.64961(12) 0.0433(4) Uani 1 1 d . . . . .
O3 O 0.3796(3) 0.8814(3) 0.70448(13) 0.0554(5) Uani 1 1 d . . . . .
O4 O 0.1755(3) 0.6877(4) 1.04818(18) 0.0766(8) Uani 1 1 d . . . . .
O5 O 0.3863(3) 0.6511(4) 1.15615(14) 0.0667(6) Uani 1 1 d . . . . .
N1 N -0.2328(2) 0.5827(3) 0.44652(13) 0.0257(4) Uani 1 1 d . . . . .
H1A H -0.320737 0.482175 0.428318 0.031 Uiso 1 1 calc R U . . .
H1B H -0.278271 0.656790 0.495539 0.031 Uiso 1 1 calc R U . . .
N2 N 0.1209(2) 0.5777(2) 0.36812(13) 0.0252(4) Uani 1 1 d . . . . .
H2 H 0.177165 0.471578 0.336613 0.030 Uiso 1 1 calc R U . . .
N3 N 0.3378(4) 0.6916(3) 1.07307(16) 0.0461(6) Uani 1 1 d . . . . .
C1 C -0.1843(3) 0.6865(3) 0.35690(17) 0.0319(5) Uani 1 1 d . . . . .
H1C H -0.138857 0.818832 0.379622 0.038 Uiso 1 1 calc R U . . .
H1D H -0.294742 0.677312 0.313008 0.038 Uiso 1 1 calc R U . . .
C2 C -0.0333(3) 0.6010(4) 0.29822(17) 0.0340(5) Uani 1 1 d . . . . .
H2A H -0.088042 0.479032 0.262453 0.041 Uiso 1 1 calc R U . . .
H2B H 0.017138 0.681931 0.247428 0.041 Uiso 1 1 calc R U . . .
C3 C 0.2742(3) 0.7419(3) 0.38882(17) 0.0316(5) Uani 1 1 d . . . . .
H3A H 0.309803 0.790302 0.324558 0.038 Uiso 1 1 calc R U . . .
H3B H 0.382787 0.700268 0.416631 0.038 Uiso 1 1 calc R U . . .
C4 C 0.2222(3) 0.8993(3) 0.46249(17) 0.0295(5) Uani 1 1 d . . . . .
H4A H 0.334432 0.990496 0.483053 0.035 Uiso 1 1 calc R U . . .
H4B H 0.136393 0.963185 0.428234 0.035 Uiso 1 1 calc R U . . .
C5 C 0.5066(3) 0.7888(3) 0.71666(17) 0.0313(5) Uani 1 1 d . . . . .
C6 C 0.5712(3) 0.7924(3) 0.82758(16) 0.0272(4) Uani 1 1 d . . . . .
C7 C 0.7566(3) 0.8224(3) 0.86150(18) 0.0309(5) Uani 1 1 d . . . . .
C8 C 0.8071(4) 0.8120(4) 0.9628(2) 0.0434(6) Uani 1 1 d . . . . .
H8 H 0.933144 0.833549 0.983418 0.052 Uiso 1 1 calc R U . . .
C9 C 0.6689(4) 0.7694(4) 1.03224(19) 0.0444(6) Uani 1 1 d . . . . .
H9 H 0.699996 0.760213 1.100092 0.053 Uiso 1 1 calc R U . . .
C10 C 0.4853(4) 0.7409(3) 0.99962(17) 0.0338(5) Uani 1 1 d . . . . .
C11 C 0.4334(3) 0.7547(3) 0.89991(17) 0.0312(5) Uani 1 1 d . . . . .
H11 H 0.306826 0.738982 0.880973 0.037 Uiso 1 1 calc R U . . .
Cl1 Cl 0.93897(9) 0.88167(10) 0.77911(5) 0.04680(18) Uani 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 2.0245(17) 2_566 ?
Cu1 N1 2.0245(17) . ?
Cu1 N2 2.0373(17) . ?
Cu1 N2 2.0373(17) 2_566 ?
O1 C4 1.420(3) . ?
O1 H1 0.8200 . ?
O2 C5 1.242(3) . ?
O3 C5 1.243(3) . ?
O4 N3 1.209(3) . ?
O5 N3 1.226(3) . ?
N1 C1 1.480(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N2 C3 1.480(3) . ?
N2 C2 1.482(3) . ?
N2 H2 0.9800 . ?
N3 C10 1.467(3) . ?
C1 C2 1.514(3) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.507(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.523(3) . ?
C6 C7 1.382(3) . ?
C6 C11 1.394(3) . ?
C7 C8 1.391(3) . ?
C7 Cl1 1.737(2) . ?
C8 C9 1.375(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.366(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(3) . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 180.0 2_566 . ?
N1 Cu1 N2 94.31(7) 2_566 . ?
N1 Cu1 N2 85.69(7) . . ?
N1 Cu1 N2 85.69(7) 2_566 2_566 ?
N1 Cu1 N2 94.31(7) . 2_566 ?
N2 Cu1 N2 180.0 . 2_566 ?
C4 O1 H1 109.5 . . ?
C1 N1 Cu1 109.45(13) . . ?
C1 N1 H1A 109.8 . . ?
Cu1 N1 H1A 109.8 . . ?
C1 N1 H1B 109.8 . . ?
Cu1 N1 H1B 109.8 . . ?
H1A N1 H1B 108.2 . . ?
C3 N2 C2 115.99(18) . . ?
C3 N2 Cu1 111.63(13) . . ?
C2 N2 Cu1 106.96(13) . . ?
C3 N2 H2 107.3 . . ?
C2 N2 H2 107.3 . . ?
Cu1 N2 H2 107.3 . . ?
O4 N3 O5 123.4(2) . . ?
O4 N3 C10 119.0(2) . . ?
O5 N3 C10 117.6(2) . . ?
N1 C1 C2 108.55(18) . . ?
N1 C1 H1C 110.0 . . ?
C2 C1 H1C 110.0 . . ?
N1 C1 H1D 110.0 . . ?
C2 C1 H1D 110.0 . . ?
H1C C1 H1D 108.4 . . ?
N2 C2 C1 111.07(17) . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 C4 113.57(17) . . ?
N2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
N2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O1 C4 C3 111.72(18) . . ?
O1 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
O1 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
O2 C5 O3 127.3(2) . . ?
O2 C5 C6 117.8(2) . . ?
O3 C5 C6 114.9(2) . . ?
C7 C6 C11 117.3(2) . . ?
C7 C6 C5 125.0(2) . . ?
C11 C6 C5 117.7(2) . . ?
C6 C7 C8 122.3(2) . . ?
C6 C7 Cl1 121.03(18) . . ?
C8 C7 Cl1 116.65(19) . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 118.7(2) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 122.4(2) . . ?
C9 C10 N3 118.8(2) . . ?
C11 C10 N3 118.8(2) . . ?
C10 C11 C6 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?

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
Cu1 N1 C1 C2 34.0(2) . . . . ?
C3 N2 C2 C1 -87.9(2) . . . . ?
Cu1 N2 C2 C1 37.3(2) . . . . ?
N1 C1 C2 N2 -48.1(3) . . . . ?
C2 N2 C3 C4 76.0(2) . . . . ?
Cu1 N2 C3 C4 -46.8(2) . . . . ?
N2 C3 C4 O1 47.9(3) . . . . ?
O2 C5 C6 C7 48.7(3) . . . . ?
O3 C5 C6 C7 -133.7(3) . . . . ?
O2 C5 C6 C11 -128.5(2) . . . . ?
O3 C5 C6 C11 49.1(3) . . . . ?
C11 C6 C7 C8 1.4(4) . . . . ?
C5 C6 C7 C8 -175.7(2) . . . . ?
C11 C6 C7 Cl1 -176.85(17) . . . . ?
C5 C6 C7 Cl1 6.0(3) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
Cl1 C7 C8 C9 178.7(2) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C8 C9 C10 N3 178.7(2) . . . . ?
O4 N3 C10 C9 171.5(3) . . . . ?
O5 N3 C10 C9 -10.5(4) . . . . ?
O4 N3 C10 C11 -9.2(4) . . . . ?
O5 N3 C10 C11 168.8(2) . . . . ?
C9 C10 C11 C6 2.4(4) . . . . ?
N3 C10 C11 C6 -176.9(2) . . . . ?
C7 C6 C11 C10 -2.7(3) . . . . ?
C5 C6 C11 C10 174.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.82 1.80 2.618(2) 171.9 . yes
N1 H1A O2 0.89 2.24 3.081(3) 158.5 2_566 yes
N1 H1B O2 0.89 2.28 3.079(2) 149.1 1_455 yes
N2 H2 O2 0.98 2.29 3.136(2) 143.9 2_666 yes
N2 H2 Cl1 0.98 2.81 3.6064(19) 138.5 2_666 yes
C1 H1C O1 0.97 2.59 3.519(3) 160.9 2_576 yes
C2 H2A Cl1 0.97 2.98 3.701(3) 131.8 2_666 yes
C3 H3A O5 0.97 2.43 3.188(3) 134.9 1_554 yes
C4 H4B O1 0.97 2.66 3.508(3) 146.6 2_576 yes
C8 H8 O4 0.93 2.39 3.185(3) 143.4 1_655 yes

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.074

