# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 1576869'
_audit_update_record             
;
2018-10-18 deposited with the CCDC.
2018-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 Cl Cu N4 O'
_chemical_formula_sum            'C18 H15 Cl Cu N4 O'
_chemical_formula_weight         402.33

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'
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'

_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                   11.1506(5)
_cell_length_b                   13.6960(6)
_cell_length_c                   11.6476(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.259(2)
_cell_angle_gamma                90
_cell_volume                     1646.25(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8092
_cell_measurement_theta_min      2.404
_cell_measurement_theta_max      27.118

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_F_000             820
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.503
_shelx_estimated_absorpt_T_min   0.864
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6141
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Apex II Quazar CCD'
_diffrn_measurement_method       'ω & φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14523
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.973
_diffrn_reflns_theta_max         27.118
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3631
_reflns_number_gt                3277
_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 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    Diamond3
_computing_publication_material  WinGX
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) 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)+(0.0375P)²+1.2159P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3631
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0752
_refine_ls_wR_factor_gt          0.0727
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
C9 C -0.03230(19) 0.50262(16) 0.81560(18) 0.0246(4) Uani 1 1 d . . . . .
H9 H -0.090915 0.531937 0.846953 0.030 Uiso 1 1 calc R U . . .
C1 C 0.09548(16) 0.63535(12) 0.53599(15) 0.0160(3) Uani 1 1 d . . . . .
C2 C 0.17456(16) 0.65930(13) 0.45868(15) 0.0165(3) Uani 1 1 d . . . . .
C3 C 0.16094(17) 0.74650(14) 0.39605(16) 0.0202(4) Uani 1 1 d . . . . .
H3 H 0.101209 0.794427 0.400383 0.024 Uiso 1 1 calc R U . . .
C4 C 0.23654(18) 0.76305(14) 0.32617(17) 0.0230(4) Uani 1 1 d . . . . .
H4 H 0.228837 0.822495 0.281908 0.028 Uiso 1 1 calc R U . . .
C5 C 0.32242(19) 0.69230(15) 0.32204(18) 0.0251(4) Uani 1 1 d . . . . .
H5 H 0.374883 0.702376 0.275097 0.030 Uiso 1 1 calc R U . . .
C6 C 0.33145(18) 0.60596(15) 0.38736(17) 0.0232(4) Uani 1 1 d . . . . .
H6 H 0.390615 0.557063 0.384345 0.028 Uiso 1 1 calc R U . . .
C7 C 0.08839(17) 0.50976(13) 0.68175(16) 0.0169(3) Uani 1 1 d . . . . .
C8 C 0.00035(18) 0.55181(14) 0.72700(16) 0.0200(4) Uani 1 1 d . . . . .
H8 H -0.036904 0.613721 0.697258 0.024 Uiso 1 1 calc R U . . .
C10 C 0.0194(2) 0.41134(15) 0.85897(17) 0.0257(4) Uani 1 1 d . . . . .
H10 H -0.003615 0.378721 0.919665 0.031 Uiso 1 1 calc R U . . .
C11 C 0.10483(19) 0.36795(14) 0.81324(17) 0.0229(4) Uani 1 1 d . . . . .
H11 H 0.139816 0.305270 0.842046 0.027 Uiso 1 1 calc R U . . .
C12 C 0.13904(17) 0.41636(13) 0.72531(16) 0.0177(3) Uani 1 1 d . . . . .
C13 C 0.34570(18) 0.33124(14) 0.75443(19) 0.0251(4) Uani 1 1 d . . . . .
H13A H 0.378260 0.282577 0.710395 0.030 Uiso 1 1 calc R U . . .
H13B H 0.331244 0.297395 0.823190 0.030 Uiso 1 1 calc R U . . .
C14 C 0.44633(18) 0.41008(14) 0.80708(17) 0.0217(4) Uani 1 1 d . . . . .
C15 C 0.5497(2) 0.39785(16) 0.91938(18) 0.0288(4) Uani 1 1 d . . . . .
H15 H 0.555960 0.340875 0.967843 0.035 Uiso 1 1 calc R U . . .
C16 C 0.6436(2) 0.46999(17) 0.9599(2) 0.0333(5) Uani 1 1 d . . . . .
H16 H 0.715874 0.462800 1.035896 0.040 Uiso 1 1 calc R U . . .
C17 C 0.6306(2) 0.55246(17) 0.8879(2) 0.0311(5) Uani 1 1 d . . . . .
H17 H 0.693055 0.603328 0.913865 0.037 Uiso 1 1 calc R U . . .
C18 C 0.52445(19) 0.55948(15) 0.77697(18) 0.0259(4) Uani 1 1 d . . . . .
H18 H 0.515435 0.616274 0.727564 0.031 Uiso 1 1 calc R U . . .
N1 N 0.25897(14) 0.58991(11) 0.45439(13) 0.0177(3) Uani 1 1 d . . . . .
N2 N 0.13419(14) 0.55108(11) 0.59632(13) 0.0164(3) Uani 1 1 d . . . . .
N3 N 0.22094(15) 0.37168(11) 0.66734(14) 0.0191(3) Uani 1 1 d . . . . .
H3A H 0.170892 0.317202 0.613120 1.000 Uiso 1 1 calc R U . . .
N4 N 0.43432(15) 0.48984(12) 0.73657(14) 0.0210(3) Uani 1 1 d . . . . .
O1 O 0.00922(12) 0.69251(9) 0.53681(12) 0.0206(3) Uani 1 1 d . . . . .
Cl1 Cl 0.33972(5) 0.36232(3) 0.46016(4) 0.02611(12) Uani 1 1 d . . . . .
Cu1 Cu 0.25885(2) 0.47315(2) 0.55657(2) 0.01661(8) 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
C9 C10 1.389(3) . ?
C9 C8 1.392(3) . ?
C9 H9 0.9500 . ?
C1 O1 1.243(2) . ?
C1 N2 1.335(2) . ?
C1 C2 1.516(2) . ?
C2 N1 1.352(2) . ?
C2 C3 1.378(3) . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 N1 1.338(2) . ?
C6 H6 0.9500 . ?
C7 N2 1.399(2) . ?
C7 C8 1.402(3) . ?
C7 C12 1.413(3) . ?
C8 H8 0.9500 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(2) . ?
C11 H11 0.9500 . ?
C12 N3 1.460(2) . ?
C13 N3 1.484(2) . ?
C13 C14 1.510(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N4 1.343(2) . ?
C14 C15 1.387(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 N4 1.335(3) . ?
C18 H18 0.9500 . ?
N1 Cu1 1.9938(15) . ?
N2 Cu1 1.9425(15) . ?
N3 Cu1 2.0464(15) . ?
N3 H3A 1.0000 . ?
N4 Cu1 2.2734(16) . ?
Cl1 Cu1 2.2683(5) . ?

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
C10 C9 C8 121.09(19) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
O1 C1 N2 129.59(16) . . ?
O1 C1 C2 119.62(15) . . ?
N2 C1 C2 110.79(15) . . ?
N1 C2 C3 121.91(16) . . ?
N1 C2 C1 116.09(15) . . ?
C3 C2 C1 122.00(16) . . ?
C2 C3 C4 118.70(17) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.25(17) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 119.17(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 121.68(18) . . ?
N1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
N2 C7 C8 126.70(17) . . ?
N2 C7 C12 114.70(16) . . ?
C8 C7 C12 118.60(16) . . ?
C9 C8 C7 119.81(18) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C11 C10 C9 119.74(18) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 119.89(18) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 120.86(17) . . ?
C11 C12 N3 122.37(16) . . ?
C7 C12 N3 116.65(15) . . ?
N3 C13 C14 111.76(15) . . ?
N3 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N3 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
N4 C14 C15 121.98(18) . . ?
N4 C14 C13 116.54(16) . . ?
C15 C14 C13 121.38(18) . . ?
C16 C15 C14 119.04(19) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C17 C16 C15 119.0(2) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 118.6(2) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
N4 C18 C17 122.8(2) . . ?
N4 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
C6 N1 C2 119.28(16) . . ?
C6 N1 Cu1 128.14(13) . . ?
C2 N1 Cu1 112.57(11) . . ?
C1 N2 C7 126.29(15) . . ?
C1 N2 Cu1 117.87(12) . . ?
C7 N2 Cu1 115.74(12) . . ?
C12 N3 C13 115.41(15) . . ?
C12 N3 Cu1 108.77(11) . . ?
C13 N3 Cu1 108.68(11) . . ?
C12 N3 H3A 107.9 . . ?
C13 N3 H3A 107.9 . . ?
Cu1 N3 H3A 107.9 . . ?
C18 N4 C14 118.57(17) . . ?
C18 N4 Cu1 131.82(13) . . ?
C14 N4 Cu1 109.51(12) . . ?
N2 Cu1 N1 82.18(6) . . ?
N2 Cu1 N3 83.43(6) . . ?
N1 Cu1 N3 165.48(6) . . ?
N2 Cu1 Cl1 160.09(5) . . ?
N1 Cu1 Cl1 98.68(4) . . ?
N3 Cu1 Cl1 94.22(5) . . ?
N2 Cu1 N4 99.70(6) . . ?
N1 Cu1 N4 105.96(6) . . ?
N3 Cu1 N4 78.35(6) . . ?
Cl1 Cu1 N4 99.16(4) . . ?

_refine_diff_density_max         0.861
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1858742'
_audit_update_record             
;
2018-07-27 deposited with the CCDC.
2018-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 Cl Cu N4 O'
_chemical_formula_sum            'C19 H15 Cl Cu N4 O'
_chemical_formula_weight         414.34

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.418(5)
_cell_length_b                   14.822(7)
_cell_length_c                   11.554(5)
_cell_angle_alpha                90
_cell_angle_beta                 118.160(5)
_cell_angle_gamma                90
_cell_volume                     1723.9(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4470
_cell_measurement_theta_min      2.426
_cell_measurement_theta_max      26.337

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_F_000             844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.438
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Apex II Quazar CCD'
_diffrn_measurement_method       'ω & φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20832
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.067
_diffrn_reflns_theta_max         26.539
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3590
_reflns_number_gt                2863
_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       Apex2
_computing_data_reduction        Apex2
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    Diamond3
_computing_publication_material  WinGX
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0201P)²+2.0469P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3590
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
C1 C 0.5783(3) 0.70604(18) 0.7101(3) 0.0250(6) Uani 1 1 d . . . . .
H1 H 0.569766 0.712172 0.787623 0.030 Uiso 1 1 calc R U . . .
C2 C 0.6790(3) 0.75194(19) 0.7014(3) 0.0301(7) Uani 1 1 d . . . . .
H2 H 0.738435 0.788971 0.771862 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6924(3) 0.74355(18) 0.5901(3) 0.0262(6) Uani 1 1 d . . . . .
H3 H 0.760818 0.774946 0.582170 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6048(3) 0.68869(17) 0.4893(3) 0.0198(6) Uani 1 1 d . . . . .
H4 H 0.612455 0.681817 0.411363 0.024 Uiso 1 1 calc R U . . .
C5 C 0.5062(2) 0.64406(15) 0.5037(2) 0.0134(5) Uani 1 1 d . . . . .
C6 C 0.4072(2) 0.58380(16) 0.3969(2) 0.0135(5) Uani 1 1 d . . . . .
C7 C 0.2086(2) 0.49667(16) 0.3527(2) 0.0134(5) Uani 1 1 d . . . . .
C8 C 0.1591(3) 0.47585(18) 0.2201(2) 0.0205(6) Uani 1 1 d . . . . .
H8 H 0.200403 0.499926 0.172251 0.025 Uiso 1 1 calc R U . . .
C9 C 0.0491(3) 0.41980(19) 0.1582(2) 0.0236(6) Uani 1 1 d . . . . .
H9 H 0.016597 0.405091 0.068189 0.028 Uiso 1 1 calc R U . . .
C10 C -0.0139(3) 0.38504(17) 0.2256(2) 0.0198(6) Uani 1 1 d . . . . .
H10 H -0.089498 0.347306 0.181193 0.024 Uiso 1 1 calc R U . . .
C11 C 0.0327(2) 0.40497(16) 0.3578(2) 0.0162(5) Uani 1 1 d . . . . .
H11 H -0.011455 0.382023 0.403698 0.019 Uiso 1 1 calc R U . . .
C12 C 0.1450(2) 0.45910(16) 0.4218(2) 0.0122(5) Uani 1 1 d . . . . .
C13 C 0.2066(2) 0.44428(16) 0.6541(2) 0.0129(5) Uani 1 1 d . . . . .
C14 C 0.1498(3) 0.35332(17) 0.6517(3) 0.0231(6) Uani 1 1 d . . . . .
H14A H 0.059799 0.359898 0.640939 0.035 Uiso 1 1 calc R U . . .
H14B H 0.205756 0.321949 0.734386 0.035 Uiso 1 1 calc R U . . .
H14C H 0.146546 0.318301 0.578319 0.035 Uiso 1 1 calc R U . . .
C15 C 0.2785(2) 0.49367(16) 0.7807(2) 0.0133(5) Uani 1 1 d . . . . .
C16 C 0.2761(2) 0.46631(18) 0.8944(2) 0.0187(6) Uani 1 1 d . . . . .
H16 H 0.230511 0.412923 0.895361 0.022 Uiso 1 1 calc R U . . .
C17 C 0.3418(3) 0.51860(19) 1.0070(2) 0.0216(6) Uani 1 1 d . . . . .
H17 H 0.342639 0.500974 1.086477 0.026 Uiso 1 1 calc R U . . .
C18 C 0.4055(3) 0.59598(18) 1.0022(2) 0.0203(6) Uani 1 1 d . . . . .
H18 H 0.448778 0.633404 1.077417 0.024 Uiso 1 1 calc R U . . .
C19 C 0.4057(3) 0.61879(17) 0.8857(2) 0.0178(5) Uani 1 1 d . . . . .
H19 H 0.450932 0.671965 0.883134 0.021 Uiso 1 1 calc R U . . .
Cl1 Cl 0.18547(6) 0.72462(4) 0.54362(6) 0.01796(14) Uani 1 1 d . . . . .
Cu1 Cu 0.32834(3) 0.58937(2) 0.59534(3) 0.01236(9) Uani 1 1 d . . . . .
N1 N 0.4919(2) 0.65298(13) 0.6131(2) 0.0159(5) Uani 1 1 d . . . . .
N2 N 0.3158(2) 0.55345(13) 0.42820(19) 0.0130(4) Uani 1 1 d . . . . .
N3 N 0.20338(19) 0.48696(13) 0.55502(18) 0.0120(4) Uani 1 1 d . . . . .
N4 N 0.3447(2) 0.56865(13) 0.77686(19) 0.0134(4) Uani 1 1 d . . . . .
O1 O 0.41836(18) 0.56950(12) 0.29642(16) 0.0230(4) 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
C1 N1 1.344(3) . ?
C1 C2 1.380(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.354(3) . ?
C5 C6 1.510(3) . ?
C6 O1 1.245(3) . ?
C6 N2 1.333(3) . ?
C7 C8 1.394(3) . ?
C7 N2 1.400(3) . ?
C7 C12 1.422(3) . ?
C8 C9 1.390(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(3) . ?
C11 H11 0.9500 . ?
C12 N3 1.420(3) . ?
C13 N3 1.293(3) . ?
C13 C15 1.489(3) . ?
C13 C14 1.491(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N4 1.357(3) . ?
C15 C16 1.387(3) . ?
C16 C17 1.391(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(4) . ?
C18 H18 0.9500 . ?
C19 N4 1.338(3) . ?
C19 H19 0.9500 . ?
Cl1 Cu1 2.4733(11) . ?
Cu1 N2 1.942(2) . ?
Cu1 N3 1.982(2) . ?
Cu1 N1 2.015(2) . ?
Cu1 N4 2.039(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.5(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 121.9(2) . . ?
N1 C5 C6 116.5(2) . . ?
C4 C5 C6 121.5(2) . . ?
O1 C6 N2 129.3(2) . . ?
O1 C6 C5 119.7(2) . . ?
N2 C6 C5 111.0(2) . . ?
C8 C7 N2 126.8(2) . . ?
C8 C7 C12 118.7(2) . . ?
N2 C7 C12 114.4(2) . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.5(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 118.9(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 N3 125.9(2) . . ?
C11 C12 C7 120.9(2) . . ?
N3 C12 C7 113.1(2) . . ?
N3 C13 C15 113.7(2) . . ?
N3 C13 C14 126.6(2) . . ?
C15 C13 C14 119.7(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 C16 122.1(2) . . ?
N4 C15 C13 115.3(2) . . ?
C16 C15 C13 122.6(2) . . ?
C15 C16 C17 118.7(2) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C18 C17 C16 119.3(2) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 119.1(2) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
N4 C19 C18 122.5(2) . . ?
N4 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
N2 Cu1 N3 81.33(8) . . ?
N2 Cu1 N1 81.90(8) . . ?
N3 Cu1 N1 155.81(8) . . ?
N2 Cu1 N4 155.42(8) . . ?
N3 Cu1 N4 80.38(8) . . ?
N1 Cu1 N4 109.59(8) . . ?
N2 Cu1 Cl1 104.54(6) . . ?
N3 Cu1 Cl1 104.15(7) . . ?
N1 Cu1 Cl1 96.86(7) . . ?
N4 Cu1 Cl1 95.77(6) . . ?
C1 N1 C5 118.2(2) . . ?
C1 N1 Cu1 129.71(18) . . ?
C5 N1 Cu1 111.92(16) . . ?
C6 N2 C7 126.9(2) . . ?
C6 N2 Cu1 118.49(16) . . ?
C7 N2 Cu1 114.64(16) . . ?
C13 N3 C12 128.3(2) . . ?
C13 N3 Cu1 116.74(16) . . ?
C12 N3 Cu1 113.28(15) . . ?
C19 N4 C15 118.4(2) . . ?
C19 N4 Cu1 129.56(17) . . ?
C15 N4 Cu1 112.05(15) . . ?

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1576873'
_audit_update_record             
;
2018-10-18 deposited with the CCDC.
2018-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H26 Cu2 N8 O6'
_chemical_formula_sum            'C40 H26 Cu2 N8 O6'
_chemical_formula_weight         841.77

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      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                   9.4219(6)
_cell_length_b                   10.0037(7)
_cell_length_c                   10.3783(7)
_cell_angle_alpha                114.711(4)
_cell_angle_beta                 98.049(5)
_cell_angle_gamma                106.462(5)
_cell_volume                     813.82(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3690
_cell_measurement_theta_min      2.262
_cell_measurement_theta_max      25.587

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.375
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4705
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Apex II Quazar CCD'
_diffrn_measurement_method       'ω & φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14401
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.262
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3319
_reflns_number_gt                2558
_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    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    Diamond3
_computing_publication_material  WinGX
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) 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)+(0.0409P)²+1.3605P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3319
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.7981(4) 0.1005(4) 0.2903(4) 0.0255(8) Uani 1 1 d . . . . .
H1 H 0.823241 0.085672 0.373958 0.031 Uiso 1 1 calc R U . . .
C2 C 0.8851(4) 0.0748(4) 0.1921(4) 0.0283(9) Uani 1 1 d . . . . .
H2 H 0.968693 0.042592 0.207717 0.034 Uiso 1 1 calc R U . . .
C3 C 0.8481(4) 0.0968(4) 0.0713(4) 0.0288(9) Uani 1 1 d . . . . .
H3 H 0.907118 0.080988 0.003019 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7249(4) 0.1419(4) 0.0495(4) 0.0261(8) Uani 1 1 d . . . . .
H4 H 0.697740 0.156816 -0.033741 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6419(4) 0.1648(4) 0.1514(4) 0.0207(7) Uani 1 1 d . . . . .
C6 C 0.5074(4) 0.2177(4) 0.1377(4) 0.0220(8) Uani 1 1 d . . . . .
C7 C 0.3448(4) 0.3104(4) 0.2920(4) 0.0219(8) Uani 1 1 d . . . . .
C8 C 0.2663(4) 0.3597(4) 0.2065(4) 0.0260(8) Uani 1 1 d . . . . .
H8 H 0.277256 0.337688 0.110880 0.031 Uiso 1 1 calc R U . . .
C9 C 0.1735(4) 0.4402(4) 0.2616(4) 0.0265(8) Uani 1 1 d . . . . .
H9 H 0.119947 0.472840 0.203079 0.032 Uiso 1 1 calc R U . . .
C10 C 0.1570(4) 0.4743(4) 0.4011(4) 0.0269(8) Uani 1 1 d . . . . .
H10 H 0.095595 0.533394 0.439112 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2297(4) 0.4224(4) 0.4856(4) 0.0247(8) Uani 1 1 d . . . . .
H11 H 0.217140 0.445329 0.580835 0.030 Uiso 1 1 calc R U . . .
C12 C 0.3216(4) 0.3362(4) 0.4313(4) 0.0208(7) Uani 1 1 d . . . . .
C13 C 0.5965(3) 0.1625(4) 0.6584(3) 0.0104(6) Uani 1 1 d . . . . .
C14 C 0.4873(4) 0.2171(4) 0.6990(4) 0.0235(8) Uani 1 1 d . . . . .
H14 H 0.470155 0.222527 0.788750 0.028 Uiso 1 1 calc R U . . .
C15 C 0.3938(4) 0.2680(4) 0.6261(4) 0.0210(7) Uani 1 1 d . . . . .
C16 C 0.2679(4) 0.2939(4) 0.6976(4) 0.0215(8) Uani 1 1 d . . . . .
C17 C 0.3032(5) 0.4185(4) 0.8381(4) 0.0278(8) Uani 1 1 d . . . . .
H17 H 0.406463 0.493476 0.890731 0.033 Uiso 1 1 calc R U . . .
C18 C 0.1836(5) 0.4308(5) 0.9001(4) 0.0325(10) Uani 1 1 d . . . . .
H18 H 0.202382 0.516914 0.995293 0.039 Uiso 1 1 calc R U . . .
C19 C 0.0368(5) 0.3163(5) 0.8214(5) 0.0329(9) Uani 1 1 d . . . . .
H19 H -0.046906 0.321312 0.862251 0.039 Uiso 1 1 calc R U . . .
C20 C 0.0128(5) 0.1935(5) 0.6819(4) 0.0318(9) Uani 1 1 d . . . . .
H20 H -0.088637 0.114193 0.629180 0.038 Uiso 1 1 calc R U . . .
N1 N 0.1258(4) 0.1812(4) 0.6178(3) 0.0271(7) Uani 1 1 d . . . . .
N2 N 0.4080(3) 0.2811(3) 0.5072(3) 0.0196(6) Uani 1 1 d . . . . .
N3 N 0.4526(3) 0.2422(3) 0.2553(3) 0.0195(6) Uani 1 1 d . . . . .
N4 N 0.6799(3) 0.1455(3) 0.2712(3) 0.0211(6) Uani 1 1 d . . . . .
O1 O 0.6590(3) 0.1058(3) 0.7276(3) 0.0326(6) Uani 1 1 d . . . . .
O2 O 0.6427(3) 0.1579(3) 0.5441(3) 0.0232(5) Uani 1 1 d . . . . .
O3 O 0.4640(3) 0.2344(3) 0.0294(3) 0.0268(6) Uani 1 1 d . . . . .
Cu1 Cu 0.54524(5) 0.20021(5) 0.40089(5) 0.02250(15) 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
C1 N4 1.334(4) . ?
C1 C2 1.382(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.376(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9500 . ?
C5 N4 1.351(4) . ?
C5 C6 1.516(5) . ?
C6 O3 1.236(4) . ?
C6 N3 1.347(4) . ?
C7 N3 1.389(4) . ?
C7 C8 1.402(5) . ?
C7 C12 1.419(5) . ?
C8 C9 1.377(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(5) . ?
C11 H11 0.9500 . ?
C12 N2 1.424(4) . ?
C13 O1 1.263(4) . ?
C13 O2 1.308(4) . ?
C13 C14 1.335(4) . ?
C14 C15 1.413(5) . ?
C14 H14 0.9500 . ?
C15 N2 1.315(4) . ?
C15 C16 1.512(5) . ?
C16 N1 1.343(5) . ?
C16 C17 1.378(5) . ?
C17 C18 1.384(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(6) . ?
C19 H19 0.9500 . ?
C20 N1 1.340(5) . ?
C20 H20 0.9500 . ?
N2 Cu1 1.946(3) . ?
N3 Cu1 1.894(3) . ?
N4 Cu1 1.995(3) . ?
O2 Cu1 1.896(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 C2 122.0(3) . . ?
N4 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 118.7(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N4 C5 C4 121.4(3) . . ?
N4 C5 C6 116.5(3) . . ?
C4 C5 C6 122.1(3) . . ?
O3 C6 N3 129.1(3) . . ?
O3 C6 C5 120.0(3) . . ?
N3 C6 C5 110.9(3) . . ?
N3 C7 C8 125.2(3) . . ?
N3 C7 C12 114.9(3) . . ?
C8 C7 C12 119.8(3) . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.9(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 118.7(3) . . ?
C11 C12 N2 126.8(3) . . ?
C7 C12 N2 114.3(3) . . ?
O1 C13 O2 115.3(3) . . ?
O1 C13 C14 120.9(3) . . ?
O2 C13 C14 123.7(3) . . ?
C13 C14 C15 128.6(3) . . ?
C13 C14 H14 115.7 . . ?
C15 C14 H14 115.7 . . ?
N2 C15 C14 124.8(3) . . ?
N2 C15 C16 124.8(3) . . ?
C14 C15 C16 110.3(3) . . ?
N1 C16 C17 124.5(3) . . ?
N1 C16 C15 114.5(3) . . ?
C17 C16 C15 120.9(3) . . ?
C16 C17 C18 117.9(4) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C19 C18 C17 118.9(4) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C20 119.1(3) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
N1 C20 C19 123.1(4) . . ?
N1 C20 H20 118.4 . . ?
C19 C20 H20 118.4 . . ?
C20 N1 C16 116.4(3) . . ?
C15 N2 C12 127.7(3) . . ?
C15 N2 Cu1 120.5(2) . . ?
C12 N2 Cu1 111.5(2) . . ?
C6 N3 C7 127.6(3) . . ?
C6 N3 Cu1 117.8(2) . . ?
C7 N3 Cu1 114.4(2) . . ?
C1 N4 C5 119.4(3) . . ?
C1 N4 Cu1 129.5(2) . . ?
C5 N4 Cu1 111.0(2) . . ?
C13 O2 Cu1 124.4(2) . . ?
N3 Cu1 O2 178.35(11) . . ?
N3 Cu1 N2 84.81(11) . . ?
O2 Cu1 N2 96.77(11) . . ?
N3 Cu1 N4 83.84(11) . . ?
O2 Cu1 N4 94.55(11) . . ?
N2 Cu1 N4 167.59(11) . . ?

_refine_diff_density_max         0.753
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1576874'
_audit_update_record             
;
2018-10-16 deposited with the CCDC.
2018-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Cl Cu N4 O2'
_chemical_formula_weight         432.36

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'
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'

_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                   8.5866(7)
_cell_length_b                   8.9466(7)
_cell_length_c                   12.3484(8)
_cell_angle_alpha                85.996(6)
_cell_angle_beta                 73.744(6)
_cell_angle_gamma                75.759(7)
_cell_volume                     882.70(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3037
_cell_measurement_theta_min      3.7600
_cell_measurement_theta_max      28.2920

_exptl_crystal_description       
;
'Fri Apr 15 02:05:46 2016'
;
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_F_000             442
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    1.412
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.42361
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
'Fri Apr 15 02:05:46 2016'
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_reflns_number            7159
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.909
_diffrn_reflns_theta_max         28.900
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4054
_reflns_number_gt                3377
_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       
;
'Fri Apr 15 02:05:46 2016'
;
_computing_cell_refinement       
;
'Fri Apr 15 02:05:46 2016'
;
_computing_data_reduction        
;
'Fri Apr 15 02:05:46 2016'
;
_computing_structure_solution    'WinGX v2014.1'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 v2014.1'
_computing_publication_material  'WinGX v2014.1'

_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)+(0.0668P)²+2.2927P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4054
_refine_ls_number_parameters     264
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1641
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.077
_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 0.37224(6) 0.51729(5) 0.33340(4) 0.01936(17) Uani 1 1 d . . . . .
Cl1 Cl 0.14142(12) 0.66764(11) 0.25130(8) 0.0221(2) Uani 1 1 d . . . . .
O1 O 0.6039(4) 0.8412(3) 0.3774(3) 0.0255(6) Uani 1 1 d . . . . .
O1W O 0.3508(5) 0.8106(4) 0.0415(3) 0.0326(7) Uani 1 1 d D . . . .
N1 N 0.5611(4) 0.5607(4) 0.2018(3) 0.0205(7) Uani 1 1 d . . . . .
N2 N 0.4264(4) 0.6767(4) 0.4048(3) 0.0224(7) Uani 1 1 d . . . . .
N3 N 0.2425(4) 0.4897(4) 0.4866(3) 0.0214(7) Uani 1 1 d . . . . .
C7 C 0.3334(5) 0.7090(5) 0.5162(3) 0.0177(8) Uani 1 1 d . . . . .
C13 C 0.1864(5) 0.3676(5) 0.5080(4) 0.0236(9) Uani 1 1 d . . . . .
N4 N 0.3274(4) 0.3059(4) 0.3149(3) 0.0246(8) Uani 1 1 d . . . . .
C2 C 0.6240(5) 0.6708(5) 0.2295(4) 0.0222(8) Uani 1 1 d . . . . .
C14 C 0.2311(5) 0.2622(5) 0.4128(4) 0.0247(9) Uani 1 1 d . . . . .
C3 C 0.7545(5) 0.7212(5) 0.1559(4) 0.0248(9) Uani 1 1 d . . . . .
H11 H 0.7969 0.7970 0.1775 0.030 Uiso 1 1 calc R U . . .
C8 C 0.3286(5) 0.8294(5) 0.5844(4) 0.0210(8) Uani 1 1 d . . . . .
H12 H 0.3951 0.8989 0.5569 0.025 Uiso 1 1 calc R U . . .
C11 C 0.1267(5) 0.6231(5) 0.6726(4) 0.0272(10) Uani 1 1 d . . . . .
H13 H 0.0604 0.5541 0.7025 0.033 Uiso 1 1 calc R U . . .
C12 C 0.2290(5) 0.6053(5) 0.5617(4) 0.0212(8) Uani 1 1 d . . . . .
C6 C 0.6238(6) 0.5006(5) 0.0997(4) 0.0260(9) Uani 1 1 d . . . . .
H15 H 0.5790 0.4248 0.0806 0.031 Uiso 1 1 calc R U . . .
C9 C 0.2252(5) 0.8443(5) 0.6922(4) 0.0265(9) Uani 1 1 d . . . . .
H16 H 0.2225 0.9250 0.7368 0.032 Uiso 1 1 calc R U . . .
C15 C 0.1767(5) 0.1247(5) 0.4235(4) 0.0266(9) Uani 1 1 d . . . . .
H17 H 0.1094 0.0978 0.4915 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3261(5) 0.0762(5) 0.2308(4) 0.0273(9) Uani 1 1 d . . . . .
H18 H 0.3620 0.0142 0.1669 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2266(5) 0.0305(5) 0.3297(4) 0.0261(9) Uani 1 1 d . . . . .
H19 H 0.1936 -0.0617 0.3332 0.031 Uiso 1 1 calc R U . . .
C4 C 0.8207(6) 0.6568(6) 0.0498(4) 0.0308(10) Uani 1 1 d . . . . .
H20 H 0.9096 0.6879 -0.0009 0.037 Uiso 1 1 calc R U . . .
C10 C 0.1251(6) 0.7432(5) 0.7368(4) 0.0275(9) Uani 1 1 d . . . . .
H21 H 0.0565 0.7564 0.8102 0.033 Uiso 1 1 calc R U . . .
C1 C 0.5494(5) 0.7407(5) 0.3469(4) 0.0222(8) Uani 1 1 d . . . . .
C18 C 0.3723(5) 0.2149(5) 0.2271(4) 0.0267(9) Uani 1 1 d . . . . .
H23 H 0.4380 0.2447 0.1595 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7537(6) 0.5453(5) 0.0193(4) 0.0298(10) Uani 1 1 d . . . . .
H24 H 0.7943 0.5019 -0.0525 0.036 Uiso 1 1 calc R U . . .
C1W C 0.2130(7) 0.9074(6) 0.0064(5) 0.0396(12) Uani 1 1 d D . . . .
H7 H 0.112(6) 0.344(5) 0.580(4) 0.017(11) Uiso 1 1 d . . . . .
H1W H 0.137(6) 0.839(6) -0.015(5) 0.10(3) Uiso 1 1 d D . . . .
H2W H 0.135(5) 0.989(5) 0.072(3) 0.061(19) Uiso 1 1 d D . . . .
H3W H 0.268(7) 0.969(6) -0.068(3) 0.11(3) Uiso 1 1 d D . . . .
H1A H 0.281(8) 0.786(10) 0.093(5) 0.10(3) Uiso 1 1 d 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 N2 1.939(4) . ?
Cu1 N3 1.942(4) . ?
Cu1 N1 2.041(4) . ?
Cu1 N4 2.060(4) . ?
Cu1 Cl1 2.5275(11) . ?
O1 C1 1.233(5) . ?
O1W C1W 1.438(6) . ?
O1W H1A 0.806(10) . ?
N1 C6 1.320(6) . ?
N1 C2 1.337(6) . ?
N2 C1 1.331(5) . ?
N2 C7 1.393(5) . ?
N3 C13 1.281(5) . ?
N3 C12 1.399(5) . ?
C7 C8 1.399(6) . ?
C7 C12 1.427(6) . ?
C13 C14 1.464(6) . ?
C13 H7 0.98(5) . ?
N4 C18 1.312(6) . ?
N4 C14 1.353(6) . ?
C2 C3 1.381(6) . ?
C2 C1 1.522(6) . ?
C14 C15 1.405(6) . ?
C3 C4 1.378(6) . ?
C3 H11 0.9300 . ?
C8 C9 1.372(6) . ?
C8 H12 0.9300 . ?
C11 C10 1.374(7) . ?
C11 C12 1.400(6) . ?
C11 H13 0.9300 . ?
C6 C5 1.391(7) . ?
C6 H15 0.9300 . ?
C9 C10 1.382(7) . ?
C9 H16 0.9300 . ?
C15 C16 1.385(6) . ?
C15 H17 0.9300 . ?
C17 C16 1.381(7) . ?
C17 C18 1.387(6) . ?
C17 H18 0.9300 . ?
C16 H19 0.9300 . ?
C4 C5 1.388(7) . ?
C4 H20 0.9300 . ?
C10 H21 0.9300 . ?
C18 H23 0.9300 . ?
C5 H24 0.9300 . ?
C1W H1W 1.090(10) . ?
C1W H2W 1.087(10) . ?
C1W H3W 1.088(10) . ?

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 N3 82.01(15) . . ?
N2 Cu1 N1 82.15(14) . . ?
N3 Cu1 N1 160.46(14) . . ?
N2 Cu1 N4 157.59(15) . . ?
N3 Cu1 N4 80.99(15) . . ?
N1 Cu1 N4 110.88(15) . . ?
N2 Cu1 Cl1 102.71(10) . . ?
N3 Cu1 Cl1 99.72(10) . . ?
N1 Cu1 Cl1 94.86(9) . . ?
N4 Cu1 Cl1 94.47(10) . . ?
C1W O1W H1A 86(6) . . ?
C6 N1 C2 118.7(4) . . ?
C6 N1 Cu1 130.8(3) . . ?
C2 N1 Cu1 110.5(3) . . ?
C1 N2 C7 126.1(4) . . ?
C1 N2 Cu1 118.9(3) . . ?
C7 N2 Cu1 115.0(3) . . ?
C13 N3 C12 128.1(4) . . ?
C13 N3 Cu1 117.5(3) . . ?
C12 N3 Cu1 114.4(3) . . ?
N2 C7 C8 128.2(4) . . ?
N2 C7 C12 113.5(4) . . ?
C8 C7 C12 118.3(4) . . ?
N3 C13 C14 115.3(4) . . ?
N3 C13 H7 126(3) . . ?
C14 C13 H7 119(3) . . ?
C18 N4 C14 118.3(4) . . ?
C18 N4 Cu1 131.3(3) . . ?
C14 N4 Cu1 110.4(3) . . ?
N1 C2 C3 122.4(4) . . ?
N1 C2 C1 118.3(4) . . ?
C3 C2 C1 119.3(4) . . ?
N4 C14 C15 122.6(4) . . ?
N4 C14 C13 115.8(4) . . ?
C15 C14 C13 121.6(4) . . ?
C4 C3 C2 118.6(4) . . ?
C4 C3 H11 120.7 . . ?
C2 C3 H11 120.7 . . ?
C9 C8 C7 119.6(4) . . ?
C9 C8 H12 120.2 . . ?
C7 C8 H12 120.2 . . ?
C10 C11 C12 119.5(4) . . ?
C10 C11 H13 120.2 . . ?
C12 C11 H13 120.2 . . ?
N3 C12 C11 125.8(4) . . ?
N3 C12 C7 113.8(4) . . ?
C11 C12 C7 120.4(4) . . ?
N1 C6 C5 123.1(4) . . ?
N1 C6 H15 118.5 . . ?
C5 C6 H15 118.5 . . ?
C8 C9 C10 122.1(4) . . ?
C8 C9 H16 118.9 . . ?
C10 C9 H16 118.9 . . ?
C16 C15 C14 117.9(4) . . ?
C16 C15 H17 121.1 . . ?
C14 C15 H17 121.1 . . ?
C16 C17 C18 119.7(4) . . ?
C16 C17 H18 120.2 . . ?
C18 C17 H18 120.2 . . ?
C17 C16 C15 118.7(4) . . ?
C17 C16 H19 120.7 . . ?
C15 C16 H19 120.7 . . ?
C3 C4 C5 119.5(4) . . ?
C3 C4 H20 120.3 . . ?
C5 C4 H20 120.3 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H21 120.0 . . ?
C9 C10 H21 120.0 . . ?
O1 C1 N2 128.7(4) . . ?
O1 C1 C2 121.1(4) . . ?
N2 C1 C2 110.2(3) . . ?
N4 C18 C17 122.8(4) . . ?
N4 C18 H23 118.6 . . ?
C17 C18 H23 118.6 . . ?
C4 C5 C6 117.6(4) . . ?
C4 C5 H24 121.2 . . ?
C6 C5 H24 121.2 . . ?
O1W C1W H1W 111(3) . . ?
O1W C1W H2W 111(3) . . ?
H1W C1W H2W 109.3(14) . . ?
O1W C1W H3W 106(3) . . ?
H1W C1W H3W 109.5(14) . . ?
H2W C1W H3W 109.7(14) . . ?

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
C1 N2 C7 C8 11.3(7) . . . . ?
Cu1 N2 C7 C8 -171.2(3) . . . . ?
C1 N2 C7 C12 -170.3(4) . . . . ?
Cu1 N2 C7 C12 7.3(4) . . . . ?
C12 N3 C13 C14 -175.7(4) . . . . ?
Cu1 N3 C13 C14 1.1(5) . . . . ?
C6 N1 C2 C3 -1.5(6) . . . . ?
Cu1 N1 C2 C3 179.4(3) . . . . ?
C6 N1 C2 C1 179.2(4) . . . . ?
Cu1 N1 C2 C1 0.1(4) . . . . ?
C18 N4 C14 C15 -0.6(6) . . . . ?
Cu1 N4 C14 C15 178.0(3) . . . . ?
C18 N4 C14 C13 179.4(4) . . . . ?
Cu1 N4 C14 C13 -2.0(4) . . . . ?
N3 C13 C14 N4 0.8(5) . . . . ?
N3 C13 C14 C15 -179.2(4) . . . . ?
N1 C2 C3 C4 0.8(6) . . . . ?
C1 C2 C3 C4 -180.0(4) . . . . ?
N2 C7 C8 C9 178.5(4) . . . . ?
C12 C7 C8 C9 0.2(6) . . . . ?
C13 N3 C12 C11 -11.4(6) . . . . ?
Cu1 N3 C12 C11 171.8(3) . . . . ?
C13 N3 C12 C7 167.9(4) . . . . ?
Cu1 N3 C12 C7 -9.0(4) . . . . ?
C10 C11 C12 N3 -179.5(4) . . . . ?
C10 C11 C12 C7 1.2(6) . . . . ?
N2 C7 C12 N3 1.1(5) . . . . ?
C8 C7 C12 N3 179.7(3) . . . . ?
N2 C7 C12 C11 -179.6(3) . . . . ?
C8 C7 C12 C11 -0.9(5) . . . . ?
C2 N1 C6 C5 0.6(6) . . . . ?
Cu1 N1 C6 C5 179.5(3) . . . . ?
C7 C8 C9 C10 0.4(6) . . . . ?
N4 C14 C15 C16 0.8(6) . . . . ?
C13 C14 C15 C16 -179.2(4) . . . . ?
C18 C17 C16 C15 -0.7(6) . . . . ?
C14 C15 C16 C17 -0.2(6) . . . . ?
C2 C3 C4 C5 0.8(7) . . . . ?
C12 C11 C10 C9 -0.7(6) . . . . ?
C8 C9 C10 C11 -0.1(6) . . . . ?
C7 N2 C1 O1 -1.5(7) . . . . ?
Cu1 N2 C1 O1 -178.9(3) . . . . ?
C7 N2 C1 C2 178.0(3) . . . . ?
Cu1 N2 C1 C2 0.5(4) . . . . ?
N1 C2 C1 O1 179.1(4) . . . . ?
C3 C2 C1 O1 -0.2(6) . . . . ?
N1 C2 C1 N2 -0.4(5) . . . . ?
C3 C2 C1 N2 -179.7(4) . . . . ?
C14 N4 C18 C17 -0.4(6) . . . . ?
Cu1 N4 C18 C17 -178.5(3) . . . . ?
C16 C17 C18 N4 1.0(7) . . . . ?
C3 C4 C5 C6 -1.7(7) . . . . ?
N1 C6 C5 C4 1.0(7) . . . . ?

_refine_diff_density_max         1.936
_refine_diff_density_min         -1.023
_refine_diff_density_rms         0.134

_shelxl_version_number           2014-3

