# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2287907'
loop_
_audit_author_name
_audit_author_address
'Prof. ENNIO ZANGRANDO'
;University of Trieste
Italy
;
_audit_update_record             
;
2024-02-19 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;

_vrf_PLAT029_2                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.950 Why?
RESPONSE: the crystal was low diffracting at higher angles. Data have not removed
 intentionally.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H24 Br2 Cl2 Cu2 N4 O2'
_chemical_formula_sum            'C28 H24 Br2 Cl2 Cu2 N4 O2'
_chemical_formula_weight         806.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   10.0356(10)
_cell_length_b                   8.9757(9)
_cell_length_c                   16.4255(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.951(2)
_cell_angle_gamma                90
_cell_volume                     1474.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6402
_cell_measurement_theta_min      5.97
_cell_measurement_theta_max      62.61

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_F_000             796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    6.900
_shelx_estimated_absorpt_T_min   0.091
_shelx_estimated_absorpt_T_max   0.545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.177
_exptl_absorpt_correction_T_max  0.596

_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause et al. J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.407
_diffrn_reflns_number            20845
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.406
_diffrn_reflns_theta_max         66.550
_diffrn_reflns_theta_full        66.550
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             2465
_reflns_number_gt                2464
_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 APEX3server_2016.5-0'
_computing_cell_refinement       'SAINT V8.37A'
_computing_data_reduction        'SAINT V8.37A'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND 3.2k,Brandenburg,K.(1999)'
_computing_publication_material  'Wingx 1.80.3 (Farrugia, 2012)'

_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)+(0.0708P)²+1.5825P] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0185(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2465
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1203
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.207
_refine_ls_restrained_S_all      1.207
_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
Cu Cu 0.40772(4) 0.57907(4) 0.55779(3) 0.0146(2) Uani 1 1 d . . . . .
Cl1 Cl 0.29478(7) 0.38660(8) 0.61645(4) 0.0208(2) Uani 1 1 d . . . . .
Br1 Br 1.07238(3) 0.56969(4) 0.80252(2) 0.0255(2) Uani 1 1 d . . . . .
N1 N 0.3495(2) 0.7822(3) 0.51201(15) 0.0174(5) Uani 1 1 d . . . . .
N2 N 0.4573(2) 0.6797(3) 0.66160(14) 0.0168(5) Uani 1 1 d . . . . .
O1 O 0.60274(19) 0.5130(2) 0.55045(12) 0.0172(5) Uani 1 1 d . . . . .
C1 C 0.3934(3) 0.8383(4) 0.44337(18) 0.0208(6) Uani 1 1 d . . . . .
H1 H 0.445672 0.777176 0.411275 0.025 Uiso 1 1 calc R U . . .
C2 C 0.3645(3) 0.9828(4) 0.41811(19) 0.0248(7) Uani 1 1 d . . . . .
H2 H 0.395584 1.019904 0.368999 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2898(4) 1.0721(3) 0.4654(2) 0.0274(8) Uani 1 1 d . . . . .
H3 H 0.270184 1.171927 0.449425 0.033 Uiso 1 1 calc R U . . .
C4 C 0.2440(3) 1.0158(4) 0.5359(2) 0.0239(7) Uani 1 1 d . . . . .
H4 H 0.192022 1.076035 0.568723 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2750(3) 0.8687(3) 0.55852(18) 0.0192(6) Uani 1 1 d . . . . .
C6 C 0.2326(3) 0.7960(4) 0.63439(19) 0.0210(6) Uani 1 1 d . . . . .
H6A H 0.186321 0.701305 0.619204 0.025 Uiso 1 1 calc R U . . .
H6B H 0.168016 0.861682 0.659190 0.025 Uiso 1 1 calc R U . . .
C7 C 0.3496(3) 0.7636(4) 0.69779(18) 0.0205(6) Uani 1 1 d . . . . .
H7A H 0.386053 0.858742 0.720573 0.025 Uiso 1 1 calc R U . . .
H7B H 0.317090 0.705019 0.743170 0.025 Uiso 1 1 calc R U . . .
C8 C 0.5744(3) 0.6835(3) 0.70014(17) 0.0174(6) Uani 1 1 d . . . . .
H8 H 0.582731 0.740279 0.749133 0.021 Uiso 1 1 calc R U . . .
C9 C 0.6949(3) 0.6117(3) 0.67772(18) 0.0166(6) Uani 1 1 d . . . . .
C10 C 0.8074(3) 0.6260(3) 0.73489(18) 0.0179(6) Uani 1 1 d . . . . .
H10 H 0.800309 0.680192 0.784012 0.022 Uiso 1 1 calc R U . . .
C11 C 0.9273(3) 0.5618(3) 0.7199(2) 0.0200(6) Uani 1 1 d . . . . .
C12 C 0.9422(3) 0.4864(4) 0.64734(19) 0.0204(6) Uani 1 1 d . . . . .
H12 H 1.025883 0.443647 0.637423 0.025 Uiso 1 1 calc R U . . .
C13 C 0.8334(3) 0.4745(3) 0.58954(18) 0.0196(6) Uani 1 1 d . . . . .
H13 H 0.844433 0.426497 0.539013 0.024 Uiso 1 1 calc R U . . .
C14 C 0.7071(3) 0.5316(3) 0.60398(18) 0.0159(6) 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
Cu O1 1.9552(19) 3_666 ?
Cu N2 1.955(2) . ?
Cu N1 2.039(2) . ?
Cu O1 2.058(2) . ?
Cu Cl1 2.3207(8) . ?
Br1 C11 1.905(3) . ?
N1 C1 1.343(4) . ?
N1 C5 1.358(4) . ?
N2 C8 1.286(4) . ?
N2 C7 1.484(4) . ?
O1 C14 1.319(4) . ?
C1 C2 1.384(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.501(4) . ?
C6 C7 1.528(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.446(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.411(4) . ?
C9 C14 1.423(4) . ?
C10 C11 1.375(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(5) . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.406(4) . ?
C13 H13 0.9500 . ?

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
O1 Cu N2 167.88(9) 3_666 . ?
O1 Cu N1 92.96(9) 3_666 . ?
N2 Cu N1 87.24(10) . . ?
O1 Cu O1 78.56(9) 3_666 . ?
N2 Cu O1 90.70(9) . . ?
N1 Cu O1 118.67(9) . . ?
O1 Cu Cl1 94.18(7) 3_666 . ?
N2 Cu Cl1 94.50(7) . . ?
N1 Cu Cl1 133.17(7) . . ?
O1 Cu Cl1 108.11(6) . . ?
C1 N1 C5 119.6(3) . . ?
C1 N1 Cu 122.7(2) . . ?
C5 N1 Cu 117.3(2) . . ?
C8 N2 C7 117.1(2) . . ?
C8 N2 Cu 126.5(2) . . ?
C7 N2 Cu 116.38(18) . . ?
C14 O1 Cu 129.56(18) . 3_666 ?
C14 O1 Cu 128.98(18) . . ?
Cu O1 Cu 101.44(9) 3_666 . ?
N1 C1 C2 121.8(3) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 120.7(3) . . ?
N1 C5 C6 115.3(3) . . ?
C4 C5 C6 124.0(3) . . ?
C5 C6 C7 113.1(3) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
N2 C7 C6 111.5(2) . . ?
N2 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N2 C8 C9 127.7(3) . . ?
N2 C8 H8 116.2 . . ?
C9 C8 H8 116.2 . . ?
C10 C9 C14 119.3(3) . . ?
C10 C9 C8 115.4(3) . . ?
C14 C9 C8 125.3(3) . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.3(3) . . ?
C10 C11 Br1 118.9(2) . . ?
C12 C11 Br1 119.8(2) . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 121.6(3) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
O1 C14 C13 121.1(3) . . ?
O1 C14 C9 120.6(3) . . ?
C13 C14 C9 118.2(3) . . ?

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 -0.2(4) . . . . ?
Cu N1 C1 C2 -172.8(2) . . . . ?
N1 C1 C2 C3 0.8(5) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C1 N1 C5 C4 -0.3(4) . . . . ?
Cu N1 C5 C4 172.7(2) . . . . ?
C1 N1 C5 C6 -179.2(3) . . . . ?
Cu N1 C5 C6 -6.3(3) . . . . ?
C3 C4 C5 N1 0.2(5) . . . . ?
C3 C4 C5 C6 179.0(3) . . . . ?
N1 C5 C6 C7 67.3(3) . . . . ?
C4 C5 C6 C7 -111.6(3) . . . . ?
C8 N2 C7 C6 160.0(3) . . . . ?
Cu N2 C7 C6 -18.1(3) . . . . ?
C5 C6 C7 N2 -52.2(3) . . . . ?
C7 N2 C8 C9 180.0(3) . . . . ?
Cu N2 C8 C9 -2.1(4) . . . . ?
N2 C8 C9 C10 -175.4(3) . . . . ?
N2 C8 C9 C14 5.2(5) . . . . ?
C14 C9 C10 C11 -0.7(4) . . . . ?
C8 C9 C10 C11 179.9(3) . . . . ?
C9 C10 C11 C12 2.3(5) . . . . ?
C9 C10 C11 Br1 -174.9(2) . . . . ?
C10 C11 C12 C13 -0.8(5) . . . . ?
Br1 C11 C12 C13 176.4(2) . . . . ?
C11 C12 C13 C14 -2.5(5) . . . . ?
Cu O1 C14 C13 -3.9(4) 3_666 . . . ?
Cu O1 C14 C13 178.0(2) . . . . ?
Cu O1 C14 C9 175.5(2) 3_666 . . . ?
Cu O1 C14 C9 -2.6(4) . . . . ?
C12 C13 C14 O1 -176.5(3) . . . . ?
C12 C13 C14 C9 4.1(4) . . . . ?
C10 C9 C14 O1 178.2(3) . . . . ?
C8 C9 C14 O1 -2.5(5) . . . . ?
C10 C9 C14 C13 -2.5(4) . . . . ?
C8 C9 C14 C13 176.9(3) . . . . ?

_refine_diff_density_max         0.851
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.154



####################################################################### 
# 
# 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_cl_cu_i_curm_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2287908'
loop_
_audit_author_name
_audit_author_address
'RIMPA MONDAL'
;UNIVERSITY OF TRIESTE
Italy
;
_audit_update_record             
;
2024-02-28 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2024-02-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H24 Cl4 Cu2 N4 O2'
_chemical_formula_sum            'C28 H24 Cl4 Cu2 N4 O2'
_chemical_formula_weight         717.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.9490(7)
_cell_length_b                   8.9918(7)
_cell_length_c                   16.3641(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.912(2)
_cell_angle_gamma                90
_cell_volume                     1456.14(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9821
_cell_measurement_temperature    183.00
_cell_measurement_theta_min      4.92
_cell_measurement_theta_max      66.99
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.457
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1177 before and 0.0750 after correction.
The Ratio of minimum to maximum transmission is 0.5680.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24910
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.980
_diffrn_reflns_theta_max         66.980
_diffrn_reflns_theta_min         8.895
_diffrn_ambient_temperature      183.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2522
_reflns_number_total             2530
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2530
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.205
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+1.0309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0962
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.40673(3) 0.41930(3) 0.55626(2) 0.01663(15) Uani 1 1 d . . . . .
Cl1 Cl 0.29176(6) 0.61294(6) 0.61267(3) 0.02486(17) Uani 1 1 d . . . . .
Cl2 Cl -0.06714(6) 0.58274(8) 0.19950(4) 0.03556(19) Uani 1 1 d . . . . .
O1 O 0.39790(14) 0.51027(17) 0.44718(9) 0.0193(3) Uani 1 1 d . . . . .
N1 N 0.54558(18) 0.6797(2) 0.33818(11) 0.0189(4) Uani 1 1 d . . . . .
N2 N 0.65391(18) 0.7837(2) 0.48933(11) 0.0189(4) Uani 1 1 d . . . . .
C1 C 0.2924(2) 0.5313(2) 0.39281(13) 0.0173(4) Uani 1 1 d . . . . .
C2 C 0.1644(2) 0.4751(3) 0.40541(14) 0.0217(5) Uani 1 1 d . . . . .
H2 H 0.153306 0.424817 0.455321 0.026 Uiso 1 1 calc R U . . .
C3 C 0.0542(2) 0.4908(3) 0.34742(14) 0.0242(5) Uani 1 1 d . . . . .
H3 H -0.030712 0.449299 0.356655 0.029 Uiso 1 1 calc R U . . .
C4 C 0.0692(2) 0.5683(3) 0.27526(15) 0.0237(5) Uani 1 1 d . . . . .
C5 C 0.1907(2) 0.6313(3) 0.26177(13) 0.0220(5) Uani 1 1 d . . . . .
H5 H 0.197846 0.687524 0.213258 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3052(2) 0.6131(2) 0.31963(13) 0.0180(4) Uani 1 1 d . . . . .
C7 C 0.4272(2) 0.6843(2) 0.29822(13) 0.0202(4) Uani 1 1 d . . . . .
H7 H 0.418932 0.741001 0.248980 0.024 Uiso 1 1 calc R U . . .
C8 C 0.6551(2) 0.7616(3) 0.30304(13) 0.0253(5) Uani 1 1 d . . . . .
H8A H 0.618796 0.856096 0.278852 0.030 Uiso 1 1 calc R U . . .
H8B H 0.688116 0.701642 0.258444 0.030 Uiso 1 1 calc R U . . .
C9 C 0.7727(2) 0.7951(3) 0.36764(14) 0.0229(5) Uani 1 1 d . . . . .
H9A H 0.819959 0.701046 0.383684 0.027 Uiso 1 1 calc R U . . .
H9B H 0.837716 0.860763 0.343165 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7297(2) 0.8686(3) 0.44339(13) 0.0218(5) Uani 1 1 d . . . . .
C11 C 0.7621(3) 1.0141(3) 0.46607(15) 0.0298(5) Uani 1 1 d . . . . .
H11 H 0.815260 1.073226 0.433583 0.036 Uiso 1 1 calc R U . . .
C12 C 0.7163(3) 1.0721(3) 0.53638(17) 0.0352(6) Uani 1 1 d . . . . .
H12 H 0.737369 1.171616 0.552391 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6399(3) 0.9845(3) 0.58317(15) 0.0300(5) Uani 1 1 d . . . . .
H13 H 0.608603 1.022478 0.631975 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6096(2) 0.8397(3) 0.55760(13) 0.0234(5) Uani 1 1 d . . . . .
H14 H 0.556253 0.779205 0.589233 0.028 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 Cl1 2.3259(6) . ?
Cu1 O1 2.0506(15) 3_666 ?
Cu1 O1 1.9572(14) . ?
Cu1 N1 1.9578(18) 3_666 ?
Cu1 N2 2.0392(18) 3_666 ?
Cl2 C4 1.746(2) . ?
O1 C1 1.318(2) . ?
N1 C7 1.288(3) . ?
N1 C8 1.479(3) . ?
N2 C10 1.355(3) . ?
N2 C14 1.341(3) . ?
C1 C2 1.404(3) . ?
C1 C6 1.422(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(3) . ?
C4 C5 1.373(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.414(3) . ?
C6 C7 1.446(3) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.524(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.505(3) . ?
C10 C11 1.388(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(4) . ?
C14 H14 0.9500 . ?

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
O1 Cu1 Cl1 106.62(5) 3_666 . ?
O1 Cu1 Cl1 94.09(5) . . ?
O1 Cu1 O1 78.43(6) . 3_666 ?
O1 Cu1 N1 168.17(7) . 3_666 ?
O1 Cu1 N2 93.25(7) . 3_666 ?
N1 Cu1 Cl1 94.29(6) 3_666 . ?
N1 Cu1 O1 91.17(7) 3_666 3_666 ?
N1 Cu1 N2 87.21(7) 3_666 3_666 ?
N2 Cu1 Cl1 132.54(5) 3_666 . ?
N2 Cu1 O1 120.79(7) 3_666 3_666 ?
Cu1 O1 Cu1 101.57(6) . 3_666 ?
C1 O1 Cu1 128.95(13) . 3_666 ?
C1 O1 Cu1 129.29(13) . . ?
C7 N1 Cu1 126.04(15) . 3_666 ?
C7 N1 C8 117.30(18) . . ?
C8 N1 Cu1 116.62(14) . 3_666 ?
C10 N2 Cu1 117.55(15) . 3_666 ?
C14 N2 Cu1 122.08(16) . 3_666 ?
C14 N2 C10 120.0(2) . . ?
O1 C1 C2 121.36(19) . . ?
O1 C1 C6 120.52(19) . . ?
C2 C1 C6 118.12(19) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 C1 122.0(2) . . ?
C3 C2 H2 119.0 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.1(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 Cl2 119.73(18) . . ?
C5 C4 Cl2 119.20(18) . . ?
C5 C4 C3 121.1(2) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 125.69(19) . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 C7 115.13(19) . . ?
N1 C7 C6 127.5(2) . . ?
N1 C7 H7 116.2 . . ?
C6 C7 H7 116.2 . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
N1 C8 C9 111.87(17) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C8 113.27(19) . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
N2 C10 C9 115.54(19) . . ?
N2 C10 C11 120.7(2) . . ?
C11 C10 C9 123.8(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.8(2) . . ?
C14 C13 H13 120.6 . . ?
N2 C14 C13 121.5(2) . . ?
N2 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?

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
Cu1 O1 C1 C2 -5.6(3) . . . . ?
Cu1 O1 C1 C2 -179.70(16) 3_666 . . . ?
Cu1 O1 C1 C6 173.89(15) . . . . ?
Cu1 O1 C1 C6 -0.2(3) 3_666 . . . ?
Cu1 N1 C7 C6 -3.0(3) 3_666 . . . ?
Cu1 N1 C8 C9 -18.3(2) 3_666 . . . ?
Cu1 N2 C10 C9 -6.3(2) 3_666 . . . ?
Cu1 N2 C10 C11 172.90(17) 3_666 . . . ?
Cu1 N2 C14 C13 -172.93(17) 3_666 . . . ?
Cl2 C4 C5 C6 -175.82(17) . . . . ?
O1 C1 C2 C3 -177.2(2) . . . . ?
O1 C1 C6 C5 178.82(19) . . . . ?
O1 C1 C6 C7 -2.4(3) . . . . ?
N1 C8 C9 C10 -51.4(3) . . . . ?
N2 C10 C11 C12 0.1(4) . . . . ?
C1 C2 C3 C4 -1.9(4) . . . . ?
C1 C6 C7 N1 4.3(4) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C2 C1 C6 C7 177.1(2) . . . . ?
C2 C3 C4 Cl2 177.40(18) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 2.8(3) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C5 C6 C7 179.8(2) . . . . ?
C5 C6 C7 N1 -176.9(2) . . . . ?
C6 C1 C2 C3 3.3(3) . . . . ?
C7 N1 C8 C9 159.4(2) . . . . ?
C8 N1 C7 C6 179.5(2) . . . . ?
C8 C9 C10 N2 66.6(3) . . . . ?
C8 C9 C10 C11 -112.5(2) . . . . ?
C9 C10 C11 C12 179.2(2) . . . . ?
C10 N2 C14 C13 -0.2(3) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C12 C13 C14 N2 0.6(4) . . . . ?
C14 N2 C10 C9 -179.36(19) . . . . ?
C14 N2 C10 C11 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
