# 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_h2b2_p212121
_database_code_depnum_ccdc_archive 'CCDC 2281188'
loop_
_audit_author_name
_audit_author_address
'Carolina Ligiero'
;Universidade Federal do Rio de Janeiro
Brazil
;
_audit_update_record             
;
2023-07-13 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        '5-methylsalicylaldehyde 2-furoyl hydrazone'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 N2 O3, H2 O'
_chemical_formula_sum            'C13 H14 N2 O4'
_chemical_formula_weight         262.26

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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.9316(2)
_cell_length_b                   12.4514(5)
_cell_length_c                   20.7391(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1273.49(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9720
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      26.58

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.724
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6762
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_special_details   
'Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-1'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-4 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22889
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.556
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2577
_reflns_number_gt                2224
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+0.1744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.2(19)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2577
_refine_ls_number_parameters     232
_refine_ls_number_restraints     238
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.002
_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
O1 O -0.2479(5) 0.71848(16) 0.38709(10) 0.0603(6) Uani 1 1 d D . . . .
O2 O 0.3217(4) 0.70371(14) 0.23232(11) 0.0596(6) Uani 1 1 d . . . . .
N1 N -0.0139(4) 0.57702(17) 0.30390(9) 0.0413(5) Uani 1 1 d . . . . .
N2 N 0.1656(5) 0.53745(16) 0.25879(10) 0.0412(5) Uani 1 1 d D . . . .
C1 C -0.3945(5) 0.6327(2) 0.40656(12) 0.0448(6) Uani 1 1 d . . . . .
C2 C -0.5846(6) 0.6472(3) 0.45507(13) 0.0543(7) Uani 1 1 d . . . . .
H2 H -0.608327 0.715016 0.472962 0.065 Uiso 1 1 calc R U . . .
C3 C -0.7386(6) 0.5627(3) 0.47714(13) 0.0556(7) Uani 1 1 d . . . . .
H3 H -0.864698 0.574707 0.509689 0.067 Uiso 1 1 calc R U . . .
C4 C -0.7103(6) 0.4592(2) 0.45185(12) 0.0496(6) Uani 1 1 d . . . . .
C5 C -0.5201(6) 0.4456(2) 0.40344(12) 0.0467(6) Uani 1 1 d . . . . .
H5 H -0.497997 0.377563 0.385642 0.056 Uiso 1 1 calc R U . . .
C6 C -0.3597(5) 0.5298(2) 0.38014(11) 0.0406(5) Uani 1 1 d . . . . .
C7 C -0.1643(5) 0.5052(2) 0.33051(11) 0.0424(5) Uani 1 1 d . . . . .
H14 H -0.146301 0.434204 0.317166 0.051 Uiso 1 1 calc R U . . .
C8 C 0.3279(5) 0.6049(2) 0.22617(11) 0.0413(5) Uani 1 1 d . . . . .
C13 C -0.8781(7) 0.3669(3) 0.47599(17) 0.0678(9) Uani 1 1 d . . . . .
H13A H -0.867775 0.308481 0.445858 0.102 Uiso 1 1 calc R U . . .
H13B H -1.063361 0.389319 0.480431 0.102 Uiso 1 1 calc R U . . .
H13C H -0.810298 0.343795 0.517115 0.102 Uiso 1 1 calc R U . . .
H1 H -0.138(8) 0.700(3) 0.3575(17) 0.102 Uiso 1 1 d D U . . .
H2A H 0.182(9) 0.469(2) 0.254(2) 0.102 Uiso 1 1 d D U . . .
O3A O 0.684(2) 0.6182(7) 0.1487(5) 0.0525(18) Uani 0.677(13) 1 d D U P A 1
C9A C 0.519(8) 0.5522(19) 0.1835(18) 0.040(3) Uani 0.677(13) 1 d D U P A 1
C10A C 0.570(3) 0.4484(9) 0.1635(4) 0.0568(19) Uani 0.677(13) 1 d D U P A 1
H10A H 0.479473 0.386897 0.176913 0.068 Uiso 0.677(13) 1 calc R U P A 1
C11A C 0.7884(16) 0.4527(6) 0.1184(4) 0.0560(19) Uani 0.677(13) 1 d D U P A 1
H11A H 0.873730 0.394798 0.098597 0.067 Uiso 0.677(13) 1 calc R U P A 1
C12A C 0.8451(18) 0.5564(8) 0.1104(4) 0.0570(17) Uani 0.677(13) 1 d D U P A 1
H12A H 0.976679 0.583027 0.082504 0.068 Uiso 0.677(13) 1 calc R U P A 1
O3B O 0.548(3) 0.4479(12) 0.1868(6) 0.061(3) Uani 0.323(13) 1 d D U P A 2
C9B C 0.513(18) 0.555(4) 0.178(4) 0.045(7) Uani 0.323(13) 1 d D U P A 2
C10B C 0.689(9) 0.602(3) 0.1350(16) 0.061(5) Uani 0.323(13) 1 d D U P A 2
H10B H 0.712844 0.673432 0.123858 0.073 Uiso 0.323(13) 1 calc R U P A 2
C11B C 0.824(4) 0.5065(18) 0.1118(9) 0.067(5) Uani 0.323(13) 1 d D U P A 2
H11B H 0.963505 0.506180 0.081563 0.080 Uiso 0.323(13) 1 calc R U P A 2
C12B C 0.724(4) 0.4205(14) 0.1393(8) 0.064(4) Uani 0.323(13) 1 d D U P A 2
H12B H 0.767677 0.350406 0.127868 0.077 Uiso 0.323(13) 1 calc R U P A 2
O4 O 0.1700(5) 0.31371(15) 0.26038(14) 0.0693(7) Uani 1 1 d D . . . .
H4A H 0.308(7) 0.277(3) 0.268(2) 0.104 Uiso 1 1 d D U . . .
H4B H 0.025(7) 0.274(3) 0.258(2) 0.104 Uiso 1 1 d 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
O1 C1 1.351(3) . ?
O2 C8 1.237(3) . ?
N1 C7 1.287(3) . ?
N1 N2 1.379(3) . ?
N2 C8 1.343(3) . ?
C1 C2 1.387(4) . ?
C1 C6 1.405(4) . ?
C2 C3 1.376(4) . ?
C3 C4 1.398(4) . ?
C4 C5 1.385(4) . ?
C4 C13 1.502(4) . ?
C5 C6 1.399(4) . ?
C6 C7 1.443(3) . ?
C8 C9A 1.450(19) . ?
C8 C9B 1.48(4) . ?
O3A C12A 1.362(8) . ?
O3A C9A 1.36(2) . ?
C9A C10A 1.38(2) . ?
C10A C11A 1.425(10) . ?
C11A C12A 1.332(9) . ?
O3B C9B 1.35(4) . ?
O3B C12B 1.357(14) . ?
C9B C10B 1.38(4) . ?
C10B C11B 1.44(2) . ?
C11B C12B 1.309(18) . ?

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
C7 N1 N2 114.4(2) . . ?
C8 N2 N1 120.1(2) . . ?
O1 C1 C2 118.4(2) . . ?
O1 C1 C6 122.6(2) . . ?
C2 C1 C6 118.9(2) . . ?
C3 C2 C1 121.0(3) . . ?
C2 C3 C4 121.7(3) . . ?
C5 C4 C3 116.9(3) . . ?
C5 C4 C13 121.4(3) . . ?
C3 C4 C13 121.7(3) . . ?
C4 C5 C6 122.8(2) . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 117.7(2) . . ?
C1 C6 C7 123.6(2) . . ?
N1 C7 C6 122.9(2) . . ?
O2 C8 N2 123.7(2) . . ?
O2 C8 C9A 121.9(11) . . ?
N2 C8 C9A 114.4(10) . . ?
O2 C8 C9B 120(2) . . ?
N2 C8 C9B 116(2) . . ?
C12A O3A C9A 108.5(12) . . ?
O3A C9A C10A 107.2(14) . . ?
O3A C9A C8 116.0(17) . . ?
C10A C9A C8 137(2) . . ?
C9A C10A C11A 107.5(12) . . ?
C12A C11A C10A 106.0(7) . . ?
C11A C12A O3A 110.6(8) . . ?
C9B O3B C12B 104(2) . . ?
O3B C9B C10B 115(3) . . ?
O3B C9B C8 114(3) . . ?
C10B C9B C8 130(4) . . ?
C9B C10B C11B 99(3) . . ?
C12B C11B C10B 111(2) . . ?
C11B C12B O3B 110.6(14) . . ?

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_CuH2B2_p21_n
_database_code_depnum_ccdc_archive 'CCDC 2281196'
loop_
_audit_author_name
_audit_author_address
'Carolina Ligiero'
;Universidade Federal do Rio de Janeiro
Brazil
;
_audit_update_record             
;
2023-10-08 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
{mu-[N-{[2-(hydroxy)-5-methylphenyl]methylidene}furan-2-carbohydrazonato]}-bis(propan-2-ol)-di-copper
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H36 Cu2 N4 O8'
_chemical_formula_sum            'C32 H36 Cu2 N4 O8'
_chemical_formula_weight         731.73

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'
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'
Cu Cu 0.3201 1.2651 '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                   6.2379(5)
_cell_length_b                   14.5843(10)
_cell_length_c                   17.5885(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.394(2)
_cell_angle_gamma                90
_cell_volume                     1595.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4976
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      23.19

_exptl_crystal_description       Needle
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.349
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    1.390
_shelx_estimated_absorpt_T_min   0.643
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6431
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and 
absorption correction
;
_exptl_absorpt_special_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
J. Appl. Cryst. 48 (2015) 3-1
;
_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-4 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25923
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.710
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3029
_reflns_number_gt                2193
_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Fo-Fc map on Cu1-O1-N1 plane shows the presence of a strong negative 
and spherical peak around Cu atom, followed by a weakest positive peak.
This effect can be explained by the truncation Fourier ripples, that 
can appear around heavy atoms
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0808P)²+1.5980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Dual
_atom_sites_solution_secondary   Difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3029
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1747
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_restrained_S_all      1.205
_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 0.83753(9) 0.57074(4) 0.47097(3) 0.0449(2) Uani 1 1 d . . . . .
O1 O 0.9407(5) 0.5106(2) 0.56544(18) 0.0478(8) Uani 1 1 d . . . . .
O2 O 0.7012(5) 0.6233(2) 0.37872(19) 0.0499(8) Uani 1 1 d . . . . .
O3 O 0.1820(6) 0.7216(3) 0.3378(2) 0.0619(10) Uani 1 1 d . . . . .
N1 N 0.5738(6) 0.6093(2) 0.5105(2) 0.0444(9) Uani 1 1 d . . . . .
N2 N 0.4265(6) 0.6494(3) 0.4566(2) 0.0451(9) Uani 1 1 d . . . . .
C1 C 0.8587(7) 0.5229(3) 0.6344(3) 0.0422(10) Uani 1 1 d . . . . .
C2 C 0.9761(8) 0.4950(3) 0.7003(3) 0.0483(11) Uani 1 1 d . . . . .
H2 H 1.112614 0.470421 0.697056 0.058 Uiso 1 1 calc R U . . .
C3 C 0.8948(8) 0.5030(3) 0.7709(3) 0.0522(12) Uani 1 1 d . . . . .
H3 H 0.978782 0.484109 0.814054 0.063 Uiso 1 1 calc R U . . .
C4 C 0.6902(8) 0.5385(3) 0.7793(3) 0.0511(12) Uani 1 1 d . . . . .
C5 C 0.5772(8) 0.5686(3) 0.7134(3) 0.0466(11) Uani 1 1 d . . . . .
H5 H 0.441832 0.594118 0.717361 0.056 Uiso 1 1 calc R U . . .
C6 C 0.6551(7) 0.5630(3) 0.6412(3) 0.0422(10) Uani 1 1 d . . . . .
C7 C 0.5169(7) 0.5979(3) 0.5792(3) 0.0448(10) Uani 1 1 d . . . . .
H7 H 0.377044 0.613531 0.588910 0.054 Uiso 1 1 calc R U . . .
C8 C 0.5118(7) 0.6522(3) 0.3908(3) 0.0435(10) Uani 1 1 d . . . . .
C9 C 0.3817(8) 0.6903(3) 0.3251(3) 0.0466(11) Uani 1 1 d . . . . .
C10 C 0.4185(9) 0.6983(4) 0.2515(3) 0.0585(13) Uani 1 1 d . . . . .
H10 H 0.542683 0.681962 0.228737 0.070 Uiso 1 1 calc R U . . .
C11 C 0.2253(10) 0.7376(4) 0.2150(4) 0.0675(16) Uani 1 1 d . . . . .
H11 H 0.199466 0.751555 0.163520 0.081 Uiso 1 1 calc R U . . .
C12 C 0.0928(10) 0.7499(4) 0.2687(4) 0.0693(16) Uani 1 1 d . . . . .
H12 H -0.044373 0.774674 0.260570 0.083 Uiso 1 1 calc R U . . .
C13 C 0.5957(11) 0.5457(5) 0.8552(3) 0.0717(16) Uani 1 1 d . . . . .
H13A H 0.541978 0.606668 0.861573 0.107 Uiso 1 1 calc R U . . .
H13B H 0.704694 0.532512 0.895192 0.107 Uiso 1 1 calc R U . . .
H13C H 0.480124 0.502517 0.857159 0.107 Uiso 1 1 calc R U . . .
O4 O 1.0365(6) 0.7068(2) 0.5110(2) 0.0523(9) Uani 1 1 d . . . . .
H4 H 1.138(10) 0.6983(19) 0.495(4) 0.078 Uiso 1 1 calc R U . . .
C14 C 0.8021(9) 0.8254(4) 0.5460(4) 0.0686(15) Uani 1 1 d . . . . .
H14A H 0.747337 0.885204 0.532520 0.103 Uiso 1 1 calc R U . . .
H14B H 0.871314 0.826952 0.596628 0.103 Uiso 1 1 calc R U . . .
H14C H 0.685657 0.782209 0.544068 0.103 Uiso 1 1 calc R U . . .
C15 C 0.9623(8) 0.7968(3) 0.4906(3) 0.0510(12) Uani 1 1 d . . . . .
H15 H 0.889498 0.794732 0.439229 0.061 Uiso 1 1 calc R U . . .
C16 C 1.1478(10) 0.8628(4) 0.4906(4) 0.0751(17) Uani 1 1 d . . . . .
H16A H 1.249323 0.841092 0.456406 0.113 Uiso 1 1 calc R U . . .
H16B H 1.216625 0.867313 0.541178 0.113 Uiso 1 1 calc R U . . .
H16C H 1.095674 0.922069 0.474225 0.113 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 1.919(4) . ?
Cu1 O2 1.932(3) . ?
Cu1 O1 1.944(3) . ?
Cu1 O1 1.967(3) 3_766 ?
Cu1 O4 2.416(4) . ?
Cu1 Cu1 3.0153(10) 3_766 ?
O1 C1 1.364(5) . ?
O2 C8 1.288(5) . ?
O3 C12 1.361(7) . ?
O3 C9 1.361(6) . ?
N1 C7 1.297(6) . ?
N1 N2 1.397(5) . ?
N2 C8 1.309(6) . ?
C1 C2 1.385(6) . ?
C1 C6 1.411(6) . ?
C2 C3 1.381(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(7) . ?
C4 C13 1.503(7) . ?
C5 C6 1.397(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.430(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.469(6) . ?
C9 C10 1.337(7) . ?
C10 C11 1.440(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.315(9) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O4 C15 1.428(6) . ?
O4 H4 0.73(6) . ?
C14 C15 1.507(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.505(7) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
N1 Cu1 O2 81.56(15) . . ?
N1 Cu1 O1 93.42(15) . . ?
O2 Cu1 O1 172.89(14) . . ?
N1 Cu1 O1 159.88(15) . 3_766 ?
O2 Cu1 O1 103.96(13) . 3_766 ?
O1 Cu1 O1 79.11(15) . 3_766 ?
N1 Cu1 O4 95.12(14) . . ?
O2 Cu1 O4 95.86(13) . . ?
O1 Cu1 O4 89.58(13) . . ?
O1 Cu1 O4 103.41(13) 3_766 . ?
N1 Cu1 Cu1 130.61(12) . 3_766 ?
O2 Cu1 Cu1 142.86(10) . 3_766 ?
O1 Cu1 Cu1 39.83(9) . 3_766 ?
O1 Cu1 Cu1 39.28(9) 3_766 3_766 ?
O4 Cu1 Cu1 98.42(8) . 3_766 ?
C1 O1 Cu1 125.3(3) . . ?
C1 O1 Cu1 133.6(3) . 3_766 ?
Cu1 O1 Cu1 100.89(15) . 3_766 ?
C8 O2 Cu1 110.0(3) . . ?
C12 O3 C9 105.8(4) . . ?
C7 N1 N2 118.3(4) . . ?
C7 N1 Cu1 127.1(3) . . ?
N2 N1 Cu1 114.5(3) . . ?
C8 N2 N1 108.8(4) . . ?
O1 C1 C2 119.7(4) . . ?
O1 C1 C6 122.1(4) . . ?
C2 C1 C6 118.2(4) . . ?
C3 C2 C1 121.4(4) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 121.8(5) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 116.2(5) . . ?
C5 C4 C13 120.8(5) . . ?
C3 C4 C13 122.9(5) . . ?
C4 C5 C6 123.6(4) . . ?
C4 C5 H5 118.2 . . ?
C6 C5 H5 118.2 . . ?
C5 C6 C1 118.6(4) . . ?
C5 C6 C7 116.1(4) . . ?
C1 C6 C7 125.2(4) . . ?
N1 C7 C6 124.4(4) . . ?
N1 C7 H7 117.8 . . ?
C6 C7 H7 117.8 . . ?
O2 C8 N2 125.2(4) . . ?
O2 C8 C9 116.9(4) . . ?
N2 C8 C9 118.0(4) . . ?
C10 C9 O3 110.9(4) . . ?
C10 C9 C8 132.0(5) . . ?
O3 C9 C8 117.1(4) . . ?
C9 C10 C11 105.5(5) . . ?
C9 C10 H10 127.3 . . ?
C11 C10 H10 127.3 . . ?
C12 C11 C10 106.5(5) . . ?
C12 C11 H11 126.7 . . ?
C10 C11 H11 126.7 . . ?
C11 C12 O3 111.3(5) . . ?
C11 C12 H12 124.3 . . ?
O3 C12 H12 124.3 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 O4 Cu1 122.2(3) . . ?
C15 O4 H4 109.5 . . ?
Cu1 O4 H4 100.8 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 C16 110.7(4) . . ?
O4 C15 C14 108.1(4) . . ?
C16 C15 C14 111.8(5) . . ?
O4 C15 H15 108.7 . . ?
C16 C15 H15 108.7 . . ?
C14 C15 H15 108.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C7 N1 N2 C8 -178.1(4) . . . . ?
Cu1 N1 N2 C8 -1.4(4) . . . . ?
Cu1 O1 C1 C2 -164.0(3) . . . . ?
Cu1 O1 C1 C2 20.9(6) 3_766 . . . ?
Cu1 O1 C1 C6 16.6(6) . . . . ?
Cu1 O1 C1 C6 -158.6(3) 3_766 . . . ?
O1 C1 C2 C3 -177.3(4) . . . . ?
C6 C1 C2 C3 2.1(7) . . . . ?
C1 C2 C3 C4 0.7(7) . . . . ?
C2 C3 C4 C5 -2.5(7) . . . . ?
C2 C3 C4 C13 178.4(5) . . . . ?
C3 C4 C5 C6 1.6(7) . . . . ?
C13 C4 C5 C6 -179.3(5) . . . . ?
C4 C5 C6 C1 1.1(7) . . . . ?
C4 C5 C6 C7 -179.7(4) . . . . ?
O1 C1 C6 C5 176.5(4) . . . . ?
C2 C1 C6 C5 -3.0(6) . . . . ?
O1 C1 C6 C7 -2.6(7) . . . . ?
C2 C1 C6 C7 177.9(4) . . . . ?
N2 N1 C7 C6 -176.1(4) . . . . ?
Cu1 N1 C7 C6 7.6(7) . . . . ?
C5 C6 C7 N1 170.5(4) . . . . ?
C1 C6 C7 N1 -10.4(7) . . . . ?
Cu1 O2 C8 N2 2.1(6) . . . . ?
Cu1 O2 C8 C9 -177.1(3) . . . . ?
N1 N2 C8 O2 -0.5(6) . . . . ?
N1 N2 C8 C9 178.8(4) . . . . ?
C12 O3 C9 C10 0.1(6) . . . . ?
C12 O3 C9 C8 -177.9(4) . . . . ?
O2 C8 C9 C10 3.0(8) . . . . ?
N2 C8 C9 C10 -176.3(5) . . . . ?
O2 C8 C9 O3 -179.5(4) . . . . ?
N2 C8 C9 O3 1.1(6) . . . . ?
O3 C9 C10 C11 -0.2(6) . . . . ?
C8 C9 C10 C11 177.4(5) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 O3 -0.2(7) . . . . ?
C9 O3 C12 C11 0.1(6) . . . . ?
Cu1 O4 C15 C16 -154.5(4) . . . . ?
Cu1 O4 C15 C14 82.8(5) . . . . ?

_refine_diff_density_max         0.750
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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 2281678'
loop_
_audit_author_name
_audit_author_address
'Renata Diniz'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2023-07-14 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 Cl Cu N2 O3, H2 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C13 H13 Cl Cu N2 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         360.25
_chemical_compound_source        'see text'

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   12.6740(4)
_cell_length_b                   6.9206(2)
_cell_length_c                   16.1553(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.109(3)
_cell_angle_gamma                90
_cell_volume                     1416.74(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    299.4(3)
_cell_measurement_reflns_used    14205
_cell_measurement_theta_min      2.5140
_cell_measurement_theta_max      30.7340
_exptl_crystal_description       prismatic
_exptl_crystal_colour            green

_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.040
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             732
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0071
-1 0 0 0.0328
0 0 1 0.0312
0 0 -1 0.0225
0 1 0 0.0957
0 -1 0 0.1066
loop_
_exptl_absorpt_coefficient_mu
1.746
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.794
_oxdiff_exptl_absorpt_empirical_full_max 1.467
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      296
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            31799
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         31.05
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             4009
# number of observed reflections (> n sig(I))
_reflns_number_gt                2953
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXL-201n (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-201n (Sheldrick, 2014)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'W=1/[Σ²(FO²)+(0.0390P)²+0.5984P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed


# Permitted for _refine_ls_hydrogen_treatment :
# refall            - refined all H-atom parameters
# refxyz            - refined H-atom coordinates only
# refU              - refined H-atom U only
# noref             - no refinement of H-atom parameters
# constr            - H-atom parameters constrained
# hetero            - H-atom parameters constrained for H on C,
#                     all H-atom parameters refined for H on
#                     heteroatoms
# heteroxyz         - H-atom parameters constrained for H on C,
#                     refined H-atom coordinates only for H
#                     on heteroatoms
# heteroU           - H-atom parameters constrained for H on C,
#                     refined H-atom U's only for H on
#                     heteroatoms
# heteronoref       - H-atom parameters constrained for H on C,
#                     no refinement of H-atom parameters for
#                     H on heteroatoms
# hetero-mixed      - H-atom parameters constrained for H on C
#                     and some heteroatoms, all H-atom
#                     parameters refined for H on remaining
#                     heteroatoms.
# heteroxyz-mixed   - H-atom parameters constrained for H on C
#                     and some heteroatoms, refined H-atom
#                     coordinates only for H on remaining
#                     heteroatoms.
# heteroU-mixed     - H-atom parameters constrained for H on C
#                     and some heteroatoms, refined H-atom
#                     U's only for H on remaining heteroatoms
# heteronoref-mixed - H-atom parameters constrained for H on C
#                     and some heteroatoms, no refinement of
#                     H-atom parameters for H on remaining
#                     heteroatoms
# mixed   - some constrained, some independent
# undef   - H-atom parameters not defined
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         4009
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.062

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu Uani 0.35868(2) 0.67657(4) 0.43166(2) 1.000 0.0354(1) d . . .
Cl Cl Uani 0.29529(5) 0.60728(10) 0.30691(3) 1.000 0.0545(2) d . . .
O1 O Uani 0.48974(12) 0.7594(2) 0.38980(8) 1.000 0.0407(4) d . . .
O2 O Uani 0.22720(11) 0.6120(2) 0.48849(9) 1.000 0.0412(5) d . . .
O3 O Uani 0.06081(13) 0.5060(3) 0.57763(11) 1.000 0.0586(6) d . . .
N1 N Uani 0.40987(13) 0.6884(2) 0.54523(10) 1.000 0.0314(5) d . . .
N2 N Uani 0.33371(13) 0.6378(2) 0.60081(10) 1.000 0.0347(5) d . . .
C1 C Uani 0.57646(17) 0.8036(3) 0.43263(13) 1.000 0.0348(6) d . . .
C2 C Uani 0.66639(18) 0.8592(3) 0.38918(14) 1.000 0.0426(7) d . . .
C3 C Uani 0.75932(18) 0.9059(3) 0.42978(15) 1.000 0.0458(7) d . . .
C4 C Uani 0.76958(17) 0.9017(3) 0.51615(15) 1.000 0.0440(7) d . . .
O4 O Uani 0.43806(14) 0.5089(3) 0.74529(10) 1.000 0.0530(6) d G . .
C5 C Uani 0.68230(17) 0.8482(3) 0.55963(14) 1.000 0.0398(7) d . . .
C6 C Uani 0.58536(16) 0.7976(3) 0.52044(12) 1.000 0.0333(6) d . . .
C7 C Uani 0.50155(16) 0.7427(3) 0.57297(12) 1.000 0.0330(6) d . . .
C8 C Uani 0.23925(16) 0.5989(3) 0.56568(12) 1.000 0.0343(6) d . . .
C9 C Uani 0.15310(16) 0.5451(3) 0.61781(13) 1.000 0.0392(6) d . . .
C10 C Uani 0.1422(2) 0.5230(5) 0.69922(16) 1.000 0.0691(10) d . . .
C11 C Uani 0.0353(2) 0.4663(5) 0.71021(19) 1.000 0.0752(13) d . . .
C12 C Uani -0.0093(2) 0.4590(5) 0.63617(19) 1.000 0.0640(10) d . . .
C13 C Uani 0.8732(2) 0.9468(5) 0.55904(19) 1.000 0.0642(10) d . . .
H2 H Uiso 0.34557 0.63167 0.65334 1.000 0.0420 c RU . .
H2A H Uiso 0.66305 0.86467 0.33167 1.000 0.0510 c RU . .
H3 H Uiso 0.81727 0.94150 0.39879 1.000 0.0550 c RU . .
H5 H Uiso 0.68706 0.84508 0.61713 1.000 0.0480 c RU . .
H7 H Uiso 0.51332 0.74597 0.62995 1.000 0.0400 c RU . .
H10 H Uiso 0.19367 0.54084 0.74030 1.000 0.0830 c RU . .
H11 H Uiso 0.00330 0.43953 0.76023 1.000 0.0900 c RU . .
H12 H Uiso -0.07946 0.42612 0.62558 1.000 0.0770 c RU . .
H13A H Uiso 0.86193 0.96594 0.61706 1.000 0.0960 c RU . .
H13B H Uiso 0.90250 1.06215 0.53579 1.000 0.0960 c RU . .
H13C H Uiso 0.92115 0.84118 0.55161 1.000 0.0960 c RU . .
H4A H Uiso 0.45526 0.59166 0.78198 1.000 0.0790 d GU . .
H4B H Uiso 0.49561 0.45281 0.73382 1.000 0.0790 d GU . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu Cl 2.2078(6) . . yes
Cu O1 1.8943(15) . . yes
Cu O2 1.9694(14) . . yes
Cu N1 1.9359(17) . . yes
O1 C1 1.323(3) . . yes
O2 C8 1.257(2) . . yes
O3 C9 1.354(3) . . yes
O3 C12 1.350(3) . . yes
N1 N2 1.376(2) . . yes
N1 C7 1.293(3) . . yes
N2 C8 1.342(3) . . yes
C1 C2 1.404(3) . . no
C1 C6 1.422(3) . . no
C2 C3 1.376(3) . . no
N2 H2 0.8600 . . no
C3 C4 1.399(3) . . no
C4 C5 1.373(3) . . no
C4 C13 1.506(3) . . no
C5 C6 1.415(3) . . no
C6 C7 1.424(3) . . no
C8 C9 1.441(3) . . no
C9 C10 1.334(3) . . no
C10 C11 1.425(4) . . no
C11 C12 1.314(4) . . no
C2 H2A 0.9300 . . no
C3 H3 0.9300 . . no
O4 H4A 0.8500 . . no
O4 H4B 0.8500 . . no
C5 H5 0.9300 . . no
C7 H7 0.9300 . . no
C10 H10 0.9300 . . no
C11 H11 0.9300 . . no
C12 H12 0.9300 . . no
C13 H13C 0.9600 . . no
C13 H13A 0.9600 . . no
C13 H13B 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl Cu O1 92.63(4) . . . yes
Cl Cu O2 94.59(5) . . . yes
Cl Cu N1 169.63(5) . . . yes
O1 Cu O2 172.21(6) . . . yes
O1 Cu N1 92.61(6) . . . yes
O2 Cu N1 80.73(7) . . . yes
Cu O1 C1 127.48(13) . . . yes
Cu O2 C8 113.04(13) . . . yes
C9 O3 C12 106.65(19) . . . yes
Cu N1 N2 112.41(12) . . . yes
Cu N1 C7 128.55(14) . . . yes
N2 N1 C7 118.99(16) . . . yes
N1 N2 C8 113.97(16) . . . yes
O1 C1 C2 118.43(19) . . . yes
O1 C1 C6 124.34(19) . . . yes
C2 C1 C6 117.23(19) . . . no
C1 C2 C3 121.5(2) . . . no
N1 N2 H2 123.00 . . . no
C8 N2 H2 123.00 . . . no
C2 C3 C4 122.2(2) . . . no
C3 C4 C13 121.2(2) . . . no
C3 C4 C5 117.1(2) . . . no
C5 C4 C13 121.7(2) . . . no
C4 C5 C6 122.6(2) . . . no
C1 C6 C7 123.84(19) . . . no
C5 C6 C7 116.78(18) . . . no
C1 C6 C5 119.38(19) . . . no
N1 C7 C6 123.14(18) . . . yes
O2 C8 C9 121.32(18) . . . yes
O2 C8 N2 119.70(18) . . . yes
N2 C8 C9 118.98(17) . . . yes
O3 C9 C10 110.2(2) . . . yes
C8 C9 C10 134.4(2) . . . no
O3 C9 C8 115.39(18) . . . yes
C9 C10 C11 105.7(2) . . . no
C10 C11 C12 106.9(3) . . . no
O3 C12 C11 110.6(2) . . . yes
C1 C2 H2A 119.00 . . . no
C3 C2 H2A 119.00 . . . no
C2 C3 H3 119.00 . . . no
C4 C3 H3 119.00 . . . no
H4A O4 H4B 104.00 . . . no
C4 C5 H5 119.00 . . . no
C6 C5 H5 119.00 . . . no
C6 C7 H7 118.00 . . . no
N1 C7 H7 118.00 . . . no
C9 C10 H10 127.00 . . . no
C11 C10 H10 127.00 . . . no
C12 C11 H11 127.00 . . . no
C10 C11 H11 127.00 . . . no
O3 C12 H12 125.00 . . . no
C11 C12 H12 125.00 . . . no
C4 C13 H13B 109.00 . . . no
C4 C13 H13C 109.00 . . . no
C4 C13 H13A 109.00 . . . no
H13A C13 H13C 109.00 . . . no
H13B C13 H13C 109.00 . . . no
H13A C13 H13B 109.00 . . . no

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
Cl Cu O1 C1 -171.24(16) . . . . no
N1 Cu O1 C1 -0.19(16) . . . . no
Cl Cu O2 C8 167.03(13) . . . . no
N1 Cu O2 C8 -3.64(14) . . . . no
O1 Cu N1 N2 179.27(11) . . . . no
O1 Cu N1 C7 2.00(17) . . . . no
O2 Cu N1 N2 3.32(11) . . . . no
O2 Cu N1 C7 -173.94(17) . . . . no
Cu O1 C1 C2 178.95(14) . . . . no
Cu O1 C1 C6 -0.7(3) . . . . no
Cu O2 C8 N2 3.3(2) . . . . no
Cu O2 C8 C9 -177.47(15) . . . . no
C12 O3 C9 C8 180.0(2) . . . . no
C12 O3 C9 C10 0.2(3) . . . . no
C9 O3 C12 C11 -0.3(3) . . . . no
Cu N1 N2 C8 -2.65(18) . . . . no
C7 N1 N2 C8 174.91(17) . . . . no
Cu N1 C7 C6 -3.0(3) . . . . no
N2 N1 C7 C6 179.94(17) . . . . no
N1 N2 C8 O2 -0.5(3) . . . . no
N1 N2 C8 C9 -179.71(16) . . . . no
O1 C1 C2 C3 -179.60(19) . . . . no
C6 C1 C2 C3 0.0(3) . . . . no
O1 C1 C6 C5 -180.0(2) . . . . no
O1 C1 C6 C7 0.1(3) . . . . no
C2 C1 C6 C5 0.4(3) . . . . no
C2 C1 C6 C7 -179.5(2) . . . . no
C1 C2 C3 C4 -0.3(3) . . . . no
C2 C3 C4 C5 0.1(3) . . . . no
C2 C3 C4 C13 177.9(2) . . . . no
C3 C4 C5 C6 0.4(3) . . . . no
C13 C4 C5 C6 -177.4(2) . . . . no
C4 C5 C6 C1 -0.7(3) . . . . no
C4 C5 C6 C7 179.3(2) . . . . no
C1 C6 C7 N1 1.8(3) . . . . no
C5 C6 C7 N1 -178.17(19) . . . . no
O2 C8 C9 O3 1.5(3) . . . . no
O2 C8 C9 C10 -178.8(3) . . . . no
N2 C8 C9 O3 -179.26(18) . . . . no
N2 C8 C9 C10 0.4(4) . . . . no
O3 C9 C10 C11 -0.1(3) . . . . no
C8 C9 C10 C11 -179.8(3) . . . . no
C9 C10 C11 C12 -0.1(4) . . . . no
C10 C11 C12 O3 0.3(4) . . . . no

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N2 H2 O4 0.8600 2.0600 2.806(2) 145.00 . yes
O4 H4A O1 0.8500 2.0600 2.897(2) 167.00 4_565 yes
O4 H4B Cl 0.8500 2.7700 3.5901(19) 161.00 3_666 yes
O4 H4B O1 0.8500 2.4900 3.021(2) 121.00 3_666 yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;

