# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_II
_database_code_depnum_ccdc_archive 'CCDC 1938699'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H30 Cu N4 O9'
_chemical_formula_weight         606.08

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.4804(11)
_cell_length_b                   10.7188(11)
_cell_length_c                   14.0027(15)
_cell_angle_alpha                72.559(5)
_cell_angle_beta                 82.036(6)
_cell_angle_gamma                78.107(6)
_cell_volume                     1323.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    34137
_cell_measurement_theta_min      2.168
_cell_measurement_theta_max      25.000

_exptl_crystal_description       block
_exptl_crystal_colour            blue


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             630
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.887
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.917

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6519
_exptl_absorpt_correction_T_max  0.7454

_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)


_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34137
_diffrn_reflns_av_unetI/netI     0.0999
_diffrn_reflns_av_R_equivalents  0.1889
_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       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.168
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4663
_reflns_number_gt                2601
_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 SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 4.1.3'
_computing_publication_material  ?
_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)+(0.0960P)²+0.1925P] 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         4663
_refine_ls_number_parameters     385
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1899
_refine_ls_wR_factor_gt          0.1458
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.037
_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 0.6299(6) 0.1548(5) 0.5462(4) 0.0370(13) Uani 1 1 d . . . . .
C2 C 0.5830(6) 0.2419(5) 0.6150(4) 0.0344(13) Uani 1 1 d . . . . .
C3 C 0.4645(6) 0.3491(5) 0.6012(4) 0.0337(13) Uani 1 1 d . . . . .
C4 C 0.4382(6) 0.4228(5) 0.6756(4) 0.0369(14) Uani 1 1 d . . . . .
C5 C 0.3246(6) 0.5321(5) 0.6684(4) 0.0424(15) Uani 1 1 d . . . . .
H5 H 0.2675 0.5608 0.6144 0.051 Uiso 1 1 calc R U . . .
C6 C 0.2995(7) 0.5955(6) 0.7424(5) 0.0488(16) Uani 1 1 d . . . . .
H6 H 0.2255 0.6683 0.7388 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3869(7) 0.5493(6) 0.8238(4) 0.0429(15) Uani 1 1 d . . . . .
C8 C 0.5182(6) 0.3869(5) 0.7580(4) 0.0361(13) Uani 1 1 d . . . . .
C9 C 0.6597(6) 0.2147(6) 0.6981(4) 0.0397(14) Uani 1 1 d . . . . .
H9 H 0.7371 0.1442 0.7066 0.048 Uiso 1 1 calc R U . . .
C10 C 0.7195(7) 0.2370(6) 0.8561(4) 0.0481(16) Uani 1 1 d . . . . .
H10A H 0.7372 0.3142 0.8720 0.058 Uiso 1 1 calc R U . . .
H10B H 0.8123 0.1869 0.8393 0.058 Uiso 1 1 calc R U . . .
C11 C 0.6450(8) 0.1524(7) 0.9461(5) 0.064(2) Uani 1 1 d . . . . .
H11A H 0.7045 0.1256 1.0014 0.096 Uiso 1 1 calc R U . . .
H11B H 0.5539 0.2022 0.9637 0.096 Uiso 1 1 calc R U . . .
H11C H 0.6289 0.0751 0.9309 0.096 Uiso 1 1 calc R U . . .
C12 C 0.3567(8) 0.6139(6) 0.9075(5) 0.0620(19) Uani 1 1 d . . . . .
H12A H 0.2756 0.6851 0.8939 0.093 Uiso 1 1 calc R U . . .
H12B H 0.3351 0.5495 0.9695 0.093 Uiso 1 1 calc R U . . .
H12C H 0.4401 0.6485 0.9128 0.093 Uiso 1 1 calc R U . . .
C13 C 0.1395(7) 0.5280(6) 0.4014(4) 0.0441(15) Uani 1 1 d . . . . .
H13 H 0.1621 0.5420 0.4595 0.053 Uiso 1 1 calc R U . . .
C14 C 0.0224(7) 0.6125(6) 0.3508(5) 0.0485(16) Uani 1 1 d . . . . .
H14 H -0.0319 0.6813 0.3748 0.058 Uiso 1 1 calc R U . . .
C15 C -0.0099(7) 0.5911(6) 0.2651(5) 0.0524(17) Uani 1 1 d . . . . .
H15 H -0.0869 0.6459 0.2304 0.063 Uiso 1 1 calc R U . . .
C16 C 0.0711(7) 0.4890(6) 0.2300(4) 0.0437(15) Uani 1 1 d . . . . .
C17 C 0.0450(7) 0.4570(6) 0.1421(5) 0.0537(17) Uani 1 1 d . . . . .
H17 H -0.0310 0.5079 0.1045 0.064 Uiso 1 1 calc R U . . .
C18 C 0.1294(8) 0.3537(7) 0.1128(5) 0.0571(18) Uani 1 1 d . . . . .
H18 H 0.1095 0.3355 0.0557 0.068 Uiso 1 1 calc R U . . .
C19 C 0.2459(7) 0.2738(6) 0.1667(4) 0.0430(15) Uani 1 1 d . . . . .
C20 C 0.3369(8) 0.1663(6) 0.1421(5) 0.0547(18) Uani 1 1 d . . . . .
H20 H 0.3218 0.1426 0.0861 0.066 Uiso 1 1 calc R U . . .
C21 C 0.4482(7) 0.0949(6) 0.1991(4) 0.0500(16) Uani 1 1 d . . . . .
H21 H 0.5094 0.0240 0.1817 0.060 Uiso 1 1 calc R U . . .
C22 C 0.4686(6) 0.1305(6) 0.2842(4) 0.0428(15) Uani 1 1 d . . . . .
H22 H 0.5442 0.0816 0.3230 0.051 Uiso 1 1 calc R U . . .
C23 C 0.2754(6) 0.3017(5) 0.2534(4) 0.0371(14) Uani 1 1 d . . . . .
C24 C 0.1862(6) 0.4087(5) 0.2847(4) 0.0346(13) Uani 1 1 d . . . . .
C25 C 0.1057(7) 0.0209(6) 0.7623(5) 0.0491(16) Uani 1 1 d . . . . .
C26 C 0.0515(9) -0.0594(7) 0.7089(5) 0.072(2) Uani 1 1 d . . . . .
H26A H 0.1037 -0.0513 0.6442 0.109 Uiso 1 1 calc R U . . .
H26B H 0.0655 -0.1510 0.7477 0.109 Uiso 1 1 calc R U . . .
H26C H -0.0497 -0.0275 0.7007 0.109 Uiso 1 1 calc R U . . .
Cu01 Cu 0.38228(8) 0.29069(7) 0.43379(5) 0.0407(3) Uani 1 1 d . . . . .
N1 N 0.6317(5) 0.2816(4) 0.7676(3) 0.0367(11) Uani 1 1 d . . . . .
N2 N 0.4945(5) 0.4501(5) 0.8309(3) 0.0431(12) Uani 1 1 d . . . . .
N3 N 0.2184(5) 0.4296(4) 0.3697(3) 0.0363(11) Uani 1 1 d . . . . .
N4 N 0.3844(5) 0.2309(4) 0.3110(3) 0.0358(11) Uani 1 1 d . . . . .
O1 O 0.3794(4) 0.3827(4) 0.5323(3) 0.0430(10) Uani 1 1 d . . . . .
O2 O 0.5589(4) 0.1726(4) 0.4725(3) 0.0446(10) Uani 1 1 d . . . . .
O1W O 0.2338(5) 0.1444(4) 0.5170(3) 0.0441(10) Uani 1 1 d D . . . .
O3 O 0.7398(4) 0.0690(4) 0.5639(3) 0.0490(11) Uani 1 1 d . . . . .
O2W O 0.0572(7) 0.1615(6) 0.9836(4) 0.0891(18) Uani 1 1 d D . . . .
O4 O 0.0483(7) 0.0204(5) 0.8474(4) 0.0890(18) Uani 1 1 d . . . . .
O3W O -0.0562(6) 0.2561(5) 0.4590(5) 0.0755(15) Uani 1 1 d D . . . .
O5 O 0.2036(5) 0.0862(5) 0.7173(3) 0.0602(12) Uani 1 1 d . . . . .
O4W O 0.3197(6) 0.1826(6) 0.8462(4) 0.0761(15) Uani 1 1 d D . . . .
H1W H 0.260(9) 0.067(5) 0.501(6) 0.114 Uiso 1 1 d D U . . .
H2W H 0.233(9) 0.112(8) 0.5847(17) 0.114 Uiso 1 1 d D U . . .
H3W H 0.015(9) 0.122(7) 1.042(2) 0.114 Uiso 1 1 d D U . . .
H4W H 0.037(7) 0.128(7) 0.937(3) 0.114 Uiso 1 1 d D U . . .
H5W H 0.039(3) 0.235(8) 0.467(7) 0.114 Uiso 1 1 d D U . . .
H6W H -0.103(8) 0.189(6) 0.486(6) 0.114 Uiso 1 1 d D U . . .
H7W H 0.265(7) 0.176(9) 0.903(3) 0.114 Uiso 1 1 d D U . . .
H8W H 0.285(8) 0.146(8) 0.806(4) 0.114 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
C1 O3 1.238(7) . ?
C1 O2 1.255(7) . ?
C1 C2 1.499(7) . ?
C2 C9 1.383(8) . ?
C2 C3 1.420(8) . ?
C3 O1 1.264(6) . ?
C3 C4 1.454(7) . ?
C4 C8 1.382(8) . ?
C4 C5 1.408(8) . ?
C5 C6 1.370(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.410(8) . ?
C6 H6 0.9300 . ?
C7 N2 1.304(7) . ?
C7 C12 1.499(7) . ?
C8 N2 1.356(7) . ?
C8 N1 1.378(7) . ?
C9 N1 1.341(7) . ?
C9 H9 0.9300 . ?
C10 N1 1.491(7) . ?
C10 C11 1.498(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N3 1.316(7) . ?
C13 C14 1.405(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(8) . ?
C15 H15 0.9300 . ?
C16 C24 1.403(8) . ?
C16 C17 1.438(8) . ?
C17 C18 1.360(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.406(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.392(8) . ?
C19 C23 1.410(7) . ?
C20 C21 1.367(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.404(8) . ?
C21 H21 0.9300 . ?
C22 N4 1.321(7) . ?
C22 H22 0.9300 . ?
C23 N4 1.355(7) . ?
C23 C24 1.423(8) . ?
C24 N3 1.359(7) . ?
C25 O4 1.238(7) . ?
C25 O5 1.261(7) . ?
C25 C26 1.497(9) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
Cu01 O2 1.915(4) . ?
Cu01 O1 1.916(4) . ?
Cu01 N4 2.003(4) . ?
Cu01 N3 2.017(5) . ?
Cu01 O1W 2.271(4) . ?
O1W H1W 0.90(2) . ?
O1W H2W 0.91(2) . ?
O2W H3W 0.89(2) . ?
O2W H4W 0.90(2) . ?
O3W H5W 0.90(2) . ?
O3W H6W 0.89(2) . ?
O4W H7W 0.882(19) . ?
O4W H8W 0.90(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C1 O2 122.6(5) . . ?
O3 C1 C2 118.0(5) . . ?
O2 C1 C2 119.4(5) . . ?
C9 C2 C3 118.0(5) . . ?
C9 C2 C1 117.6(5) . . ?
C3 C2 C1 124.5(5) . . ?
O1 C3 C2 125.9(5) . . ?
O1 C3 C4 118.2(5) . . ?
C2 C3 C4 115.9(5) . . ?
C8 C4 C5 117.0(5) . . ?
C8 C4 C3 122.4(5) . . ?
C5 C4 C3 120.6(5) . . ?
C6 C5 C4 118.9(5) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C7 119.4(6) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
N2 C7 C6 122.7(5) . . ?
N2 C7 C12 117.3(6) . . ?
C6 C7 C12 120.0(6) . . ?
N2 C8 N1 116.6(5) . . ?
N2 C8 C4 124.4(5) . . ?
N1 C8 C4 119.1(5) . . ?
N1 C9 C2 125.4(5) . . ?
N1 C9 H9 117.3 . . ?
C2 C9 H9 117.3 . . ?
N1 C10 C11 111.8(5) . . ?
N1 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 122.5(5) . . ?
N3 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C15 C14 C13 118.3(6) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C16 120.5(6) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C24 117.8(5) . . ?
C15 C16 C17 124.9(6) . . ?
C24 C16 C17 117.3(6) . . ?
C18 C17 C16 121.3(6) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 121.7(6) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C20 C19 C18 125.3(6) . . ?
C20 C19 C23 115.8(6) . . ?
C18 C19 C23 118.9(6) . . ?
C21 C20 C19 121.0(6) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 119.0(6) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
N4 C22 C21 122.3(6) . . ?
N4 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
N4 C23 C19 123.9(5) . . ?
N4 C23 C24 116.7(5) . . ?
C19 C23 C24 119.4(5) . . ?
N3 C24 C16 121.8(5) . . ?
N3 C24 C23 116.8(5) . . ?
C16 C24 C23 121.4(5) . . ?
O4 C25 O5 124.7(6) . . ?
O4 C25 C26 117.0(7) . . ?
O5 C25 C26 118.2(6) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O2 Cu01 O1 93.82(16) . . ?
O2 Cu01 N4 92.45(17) . . ?
O1 Cu01 N4 168.40(17) . . ?
O2 Cu01 N3 169.41(18) . . ?
O1 Cu01 N3 89.91(17) . . ?
N4 Cu01 N3 82.28(18) . . ?
O2 Cu01 O1W 95.89(16) . . ?
O1 Cu01 O1W 100.01(16) . . ?
N4 Cu01 O1W 89.03(16) . . ?
N3 Cu01 O1W 93.21(17) . . ?
C9 N1 C8 119.3(5) . . ?
C9 N1 C10 119.5(5) . . ?
C8 N1 C10 121.2(4) . . ?
C7 N2 C8 117.7(5) . . ?
C13 N3 C24 119.1(5) . . ?
C13 N3 Cu01 129.2(4) . . ?
C24 N3 Cu01 111.6(4) . . ?
C22 N4 C23 118.2(5) . . ?
C22 N4 Cu01 129.4(4) . . ?
C23 N4 Cu01 112.3(3) . . ?
C3 O1 Cu01 125.4(3) . . ?
C1 O2 Cu01 130.3(4) . . ?
Cu01 O1W H1W 112(6) . . ?
Cu01 O1W H2W 119(5) . . ?
H1W O1W H2W 98(7) . . ?
H3W O2W H4W 108(3) . . ?
H5W O3W H6W 113(8) . . ?
H7W O4W H8W 110(3) . . ?

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.089

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

####################################################################### 
# 
# 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_III
_database_code_depnum_ccdc_archive 'CCDC 1938700'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 Cu N5 O7'
_chemical_formula_weight         555.00

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.9957(9)
_cell_length_b                   12.0271(11)
_cell_length_c                   12.6970(14)
_cell_angle_alpha                94.074(5)
_cell_angle_beta                 97.486(6)
_cell_angle_gamma                108.309(5)
_cell_volume                     1141.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    35549
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      24.998

_exptl_crystal_description       needle
_exptl_crystal_colour            blue


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_F_000             570
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.016
_shelx_estimated_absorpt_T_min   0.771
_shelx_estimated_absorpt_T_max   0.990

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_correction_T_max  0.7454

_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)


_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35549
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.1155
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.277
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4025
_reflns_number_gt                2785
_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 SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 4.1.3'
_computing_publication_material  ?
_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)+(0.0613P)²+2.0282P] 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         4025
_refine_ls_number_parameters     340
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.039
_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 0.7754(6) 0.1680(4) 0.5321(3) 0.0371(10) Uani 1 1 d . . . . .
C2 C 0.6537(6) 0.1665(4) 0.4317(3) 0.0353(10) Uani 1 1 d . . . . .
C3 C 0.6209(6) 0.2673(4) 0.3956(3) 0.0327(9) Uani 1 1 d . . . . .
C4 C 0.5075(6) 0.2495(4) 0.2933(3) 0.0338(10) Uani 1 1 d . . . . .
C5 C 0.4327(6) 0.1378(4) 0.2341(3) 0.0408(11) Uani 1 1 d . . . . .
C6 C 0.5734(7) 0.0596(4) 0.3698(4) 0.0475(12) Uani 1 1 d . . . . .
H6 H 0.5964 -0.0059 0.3948 0.057 Uiso 1 1 calc R U . . .
C7 C 0.4664(6) 0.3423(4) 0.2477(4) 0.0427(11) Uani 1 1 d . . . . .
H7 H 0.5111 0.4183 0.2835 0.051 Uiso 1 1 calc R U . . .
C8 C 0.3603(7) 0.3202(5) 0.1501(4) 0.0514(13) Uani 1 1 d . . . . .
H8 H 0.3322 0.3812 0.1192 0.062 Uiso 1 1 calc R U . . .
N1 N 0.3280(6) 0.1156(3) 0.1383(3) 0.0503(10) Uani 1 1 d . . . . .
C10 C 0.3730(10) -0.0810(5) 0.2181(5) 0.079(2) Uani 1 1 d . . . . .
H10A H 0.3654 -0.1395 0.2677 0.095 Uiso 1 1 calc R U . . .
H10B H 0.2531 -0.0890 0.1844 0.095 Uiso 1 1 calc R U . . .
C11 C 0.4778(10) -0.0972(6) 0.1393(6) 0.086(2) Uani 1 1 d . . . . .
H11A H 0.4239 -0.1745 0.1004 0.129 Uiso 1 1 calc R U . . .
H11B H 0.4842 -0.0389 0.0908 0.129 Uiso 1 1 calc R U . . .
H11C H 0.5960 -0.0891 0.1738 0.129 Uiso 1 1 calc R U . . .
C12 C 0.1795(8) 0.1787(5) -0.0120(4) 0.0643(16) Uani 1 1 d . . . . .
H12A H 0.1637 0.2500 -0.0339 0.096 Uiso 1 1 calc R U . . .
H12B H 0.2368 0.1469 -0.0627 0.096 Uiso 1 1 calc R U . . .
H12C H 0.0653 0.1223 -0.0087 0.096 Uiso 1 1 calc R U . . .
C13 C 0.7558(6) 0.6302(4) 0.5061(4) 0.0423(11) Uani 1 1 d . . . . .
H13 H 0.6835 0.5819 0.4460 0.051 Uiso 1 1 calc R U . . .
C14 C 0.7752(6) 0.7499(4) 0.5161(4) 0.0445(11) Uani 1 1 d . . . . .
H14 H 0.7162 0.7801 0.4632 0.053 Uiso 1 1 calc R U . . .
C15 C 0.8805(6) 0.8227(4) 0.6030(4) 0.0439(11) Uani 1 1 d . . . . .
H15 H 0.8950 0.9028 0.6096 0.053 Uiso 1 1 calc R U . . .
C16 C 0.9669(6) 0.7753(4) 0.6827(4) 0.0397(11) Uani 1 1 d . . . . .
C17 C 1.0761(7) 0.8418(4) 0.7791(4) 0.0493(12) Uani 1 1 d . . . . .
H17 H 1.0956 0.9224 0.7908 0.059 Uiso 1 1 calc R U . . .
C18 C 1.1513(7) 0.7896(4) 0.8536(4) 0.0496(12) Uani 1 1 d . . . . .
H18 H 1.2204 0.8349 0.9160 0.060 Uiso 1 1 calc R U . . .
C19 C 1.1271(6) 0.6662(4) 0.8386(4) 0.0425(11) Uani 1 1 d . . . . .
C20 C 1.2001(7) 0.6055(5) 0.9122(4) 0.0544(14) Uani 1 1 d . . . . .
H20 H 1.2678 0.6450 0.9771 0.065 Uiso 1 1 calc R U . . .
C21 C 1.1705(7) 0.4881(5) 0.8874(4) 0.0602(15) Uani 1 1 d . . . . .
H21 H 1.2190 0.4472 0.9354 0.072 Uiso 1 1 calc R U . . .
C22 C 1.0675(7) 0.4288(4) 0.7900(4) 0.0472(12) Uani 1 1 d . . . . .
H22 H 1.0497 0.3488 0.7742 0.057 Uiso 1 1 calc R U . . .
C23 C 1.0242(6) 0.6002(4) 0.7442(3) 0.0341(10) Uani 1 1 d . . . . .
C24 C 0.9410(6) 0.6551(4) 0.6665(3) 0.0349(10) Uani 1 1 d . . . . .
Cu01 Cu 0.82258(8) 0.41421(5) 0.58567(4) 0.0387(2) Uani 1 1 d . . . . .
C9 C 0.2938(7) 0.2052(5) 0.0968(4) 0.0483(12) Uani 1 1 d . . . . .
N2 N 0.4652(6) 0.0427(3) 0.2769(3) 0.0542(11) Uani 1 1 d . . . . .
N3 N 0.8364(5) 0.5824(3) 0.5793(3) 0.0343(8) Uani 1 1 d . . . . .
N4 N 0.9955(5) 0.4827(3) 0.7206(3) 0.0372(9) Uani 1 1 d . . . . .
N5 N 0.5463(6) 0.3672(3) 0.7611(4) 0.0462(10) Uani 1 1 d . . . . .
O1 O 0.6832(4) 0.3710(2) 0.4455(2) 0.0414(8) Uani 1 1 d . . . . .
O2 O 0.8549(4) 0.2646(3) 0.5918(2) 0.0464(8) Uani 1 1 d . . . . .
O1W O 1.1021(8) 0.1150(4) 0.7173(4) 0.1003(18) Uani 1 1 d D . . . .
O3 O 0.7979(5) 0.0743(3) 0.5533(3) 0.0519(9) Uani 1 1 d . . . . .
O4 O 0.5695(5) 0.3655(5) 0.6683(3) 0.0834(14) Uani 1 1 d . . . . .
O5 O 0.3967(7) 0.3341(5) 0.7817(4) 0.1017(16) Uani 1 1 d . . . . .
O6 O 0.6722(6) 0.4088(4) 0.8335(3) 0.0886(14) Uani 1 1 d . . . . .
H1W H 1.004(7) 0.110(7) 0.671(5) 0.133 Uiso 1 1 d D U . . .
H2W H 1.195(7) 0.182(4) 0.724(7) 0.133 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
C1 O3 1.238(5) . ?
C1 O2 1.271(5) . ?
C1 C2 1.496(6) . ?
C2 C6 1.374(6) . ?
C2 C3 1.413(6) . ?
C3 O1 1.273(5) . ?
C3 C4 1.445(6) . ?
C4 C7 1.400(6) . ?
C4 C5 1.401(6) . ?
C5 N1 1.341(6) . ?
C5 N2 1.382(6) . ?
C6 N2 1.332(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.364(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.402(7) . ?
C8 H8 0.9300 . ?
N1 C9 1.319(6) . ?
C10 C11 1.426(9) . ?
C10 N2 1.525(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C9 1.507(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N3 1.327(5) . ?
C13 C14 1.394(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.405(6) . ?
C15 H15 0.9300 . ?
C16 C24 1.390(6) . ?
C16 C17 1.430(6) . ?
C17 C18 1.350(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.430(7) . ?
C18 H18 0.9300 . ?
C19 C23 1.394(6) . ?
C19 C20 1.402(7) . ?
C20 C21 1.363(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.398(7) . ?
C21 H21 0.9300 . ?
C22 N4 1.309(6) . ?
C22 H22 0.9300 . ?
C23 N4 1.363(5) . ?
C23 C24 1.432(6) . ?
C24 N3 1.361(5) . ?
Cu01 O2 1.902(3) . ?
Cu01 O1 1.915(3) . ?
Cu01 N4 1.998(4) . ?
Cu01 N3 1.999(3) . ?
Cu01 O4 2.331(4) . ?
N5 O5 1.206(6) . ?
N5 O4 1.216(5) . ?
N5 O6 1.219(5) . ?
O1W H1W 0.89(2) . ?
O1W H2W 0.90(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C1 O2 122.0(4) . . ?
O3 C1 C2 118.4(4) . . ?
O2 C1 C2 119.6(4) . . ?
C6 C2 C3 118.7(4) . . ?
C6 C2 C1 116.9(4) . . ?
C3 C2 C1 124.4(4) . . ?
O1 C3 C2 125.4(4) . . ?
O1 C3 C4 118.2(4) . . ?
C2 C3 C4 116.4(4) . . ?
C7 C4 C5 116.3(4) . . ?
C7 C4 C3 122.2(4) . . ?
C5 C4 C3 121.5(4) . . ?
N1 C5 N2 117.0(4) . . ?
N1 C5 C4 124.4(4) . . ?
N2 C5 C4 118.6(4) . . ?
N2 C6 C2 124.9(4) . . ?
N2 C6 H6 117.6 . . ?
C2 C6 H6 117.6 . . ?
C8 C7 C4 119.5(4) . . ?
C8 C7 H7 120.3 . . ?
C4 C7 H7 120.3 . . ?
C7 C8 C9 119.8(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C9 N1 C5 117.8(4) . . ?
C11 C10 N2 106.9(6) . . ?
C11 C10 H10A 110.3 . . ?
N2 C10 H10A 110.3 . . ?
C11 C10 H10B 110.3 . . ?
N2 C10 H10B 110.3 . . ?
H10A C10 H10B 108.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 122.5(4) . . ?
N3 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.2(4) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C24 C16 C15 117.1(4) . . ?
C24 C16 C17 118.5(4) . . ?
C15 C16 C17 124.5(4) . . ?
C18 C17 C16 121.2(4) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 121.5(4) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C23 C19 C20 116.8(4) . . ?
C23 C19 C18 118.3(4) . . ?
C20 C19 C18 124.9(4) . . ?
C21 C20 C19 119.2(5) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 120.3(5) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
N4 C22 C21 121.9(4) . . ?
N4 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
N4 C23 C19 123.3(4) . . ?
N4 C23 C24 116.6(4) . . ?
C19 C23 C24 120.1(4) . . ?
N3 C24 C16 123.7(4) . . ?
N3 C24 C23 115.8(4) . . ?
C16 C24 C23 120.4(4) . . ?
O2 Cu01 O1 93.69(12) . . ?
O2 Cu01 N4 92.02(13) . . ?
O1 Cu01 N4 169.92(14) . . ?
O2 Cu01 N3 169.58(15) . . ?
O1 Cu01 N3 90.54(13) . . ?
N4 Cu01 N3 82.50(14) . . ?
O2 Cu01 O4 94.65(17) . . ?
O1 Cu01 O4 92.50(14) . . ?
N4 Cu01 O4 95.32(14) . . ?
N3 Cu01 O4 94.67(16) . . ?
N1 C9 C8 122.3(4) . . ?
N1 C9 C12 116.8(4) . . ?
C8 C9 C12 120.9(4) . . ?
C6 N2 C5 119.8(4) . . ?
C6 N2 C10 120.7(4) . . ?
C5 N2 C10 119.5(4) . . ?
C13 N3 C24 117.4(4) . . ?
C13 N3 Cu01 129.8(3) . . ?
C24 N3 Cu01 112.7(3) . . ?
C22 N4 C23 118.5(4) . . ?
C22 N4 Cu01 129.0(3) . . ?
C23 N4 Cu01 112.2(3) . . ?
O5 N5 O4 119.9(5) . . ?
O5 N5 O6 119.4(5) . . ?
O4 N5 O6 120.6(5) . . ?
C3 O1 Cu01 125.7(3) . . ?
C1 O2 Cu01 129.7(3) . . ?
H1W O1W H2W 117(7) . . ?
N5 O4 Cu01 133.8(3) . . ?

_refine_diff_density_max         0.813
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.078

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1938701'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 Cu0.50 N2 O4'
_chemical_formula_weight         281.01

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.2633(5)
_cell_length_b                   7.4357(4)
_cell_length_c                   19.1577(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.821(2)
_cell_angle_gamma                90
_cell_volume                     1159.86(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2663
_cell_measurement_theta_min      2.501
_cell_measurement_theta_max      27.492

_exptl_crystal_description       Plate
_exptl_crystal_colour            Blue


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_F_000             582
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.002
_shelx_estimated_absorpt_T_min   0.795
_shelx_estimated_absorpt_T_max   0.980

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6132
_exptl_absorpt_correction_T_max  0.7461

_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)


_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17756
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.501
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2663
_reflns_number_gt                1905
_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 SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 4.1.3'
_computing_publication_material  ?
_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)+(0.0482P)²+1.6015P] 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         2663
_refine_ls_number_parameters     175
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1277
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.075
_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
C1 C 0.8761(4) 0.4383(4) 0.63070(17) 0.0313(7) Uani 1 1 d . . . . .
C2 C 0.7189(3) 0.3695(4) 0.58831(16) 0.0272(6) Uani 1 1 d . . . . .
C3 C 0.6940(3) 0.3378(4) 0.51462(16) 0.0272(6) Uani 1 1 d . . . . .
C4 C 0.5361(3) 0.2628(4) 0.48353(16) 0.0270(6) Uani 1 1 d . . . . .
C5 C 0.4124(3) 0.2351(4) 0.52459(17) 0.0298(7) Uani 1 1 d . . . . .
C6 C 0.5923(4) 0.3376(4) 0.62485(17) 0.0341(7) Uani 1 1 d . . . . .
H6 H 0.6111 0.3604 0.6733 0.041 Uiso 1 1 calc R U . . .
C7 C 0.4981(4) 0.2168(4) 0.41222(18) 0.0350(7) Uani 1 1 d . . . . .
H7 H 0.5751 0.2339 0.3827 0.042 Uiso 1 1 calc R U . . .
C8 C 0.3469(4) 0.1461(5) 0.38561(19) 0.0392(8) Uani 1 1 d . . . . .
H8 H 0.3218 0.1115 0.3383 0.047 Uiso 1 1 calc R U . . .
C9 C 0.2303(4) 0.1265(4) 0.43053(19) 0.0349(7) Uani 1 1 d . . . . .
C10 C 0.3158(4) 0.2553(9) 0.6413(2) 0.0759(16) Uani 1 1 d . . . . .
H10A H 0.2861 0.3747 0.6552 0.091 Uiso 1 1 calc R U . . .
H10B H 0.2191 0.2042 0.6123 0.091 Uiso 1 1 calc R U . . .
C11 C 0.3508(6) 0.1550(10) 0.7005(3) 0.111(3) Uani 1 1 d . . . . .
H11A H 0.2576 0.1534 0.7244 0.167 Uiso 1 1 calc R U . . .
H11B H 0.3762 0.0345 0.6881 0.167 Uiso 1 1 calc R U . . .
H11C H 0.4435 0.2057 0.7313 0.167 Uiso 1 1 calc R U . . .
C12 C 0.0628(4) 0.0529(5) 0.4030(2) 0.0482(10) Uani 1 1 d . . . . .
H12A H 0.0544 0.0251 0.3536 0.072 Uiso 1 1 calc R U . . .
H12B H 0.0454 -0.0544 0.4286 0.072 Uiso 1 1 calc R U . . .
H12C H -0.0187 0.1408 0.4092 0.072 Uiso 1 1 calc R U . . .
Cu01 Cu 1.0000 0.5000 0.5000 0.03135(18) Uani 1 2 d S . P . .
N1 N 0.4444(3) 0.2762(4) 0.59580(14) 0.0373(7) Uani 1 1 d . . . . .
N2 N 0.2616(3) 0.1717(4) 0.49845(15) 0.0363(6) Uani 1 1 d . . . . .
O1 O 0.7975(3) 0.3696(3) 0.47396(12) 0.0365(5) Uani 1 1 d . . . . .
O2 O 0.9877(3) 0.4966(3) 0.59764(12) 0.0361(5) Uani 1 1 d . . . . .
O1W O 0.7738(4) 0.1646(6) 0.7783(3) 0.1092(17) Uani 1 1 d D . . . .
O3 O 0.8936(3) 0.4381(4) 0.69521(13) 0.0505(7) Uani 1 1 d . . . . .
H3W H 0.842(6) 0.092(4) 0.758(3) 0.076 Uiso 1 1 d D U . . .
H4W H 0.817(5) 0.272(3) 0.765(2) 0.076 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
C1 O3 1.220(4) . ?
C1 O2 1.280(4) . ?
C1 C2 1.499(4) . ?
C2 C6 1.375(4) . ?
C2 C3 1.411(4) . ?
C3 O1 1.273(3) . ?
C3 C4 1.450(4) . ?
C4 C7 1.391(4) . ?
C4 C5 1.408(4) . ?
C5 N2 1.346(4) . ?
C5 N1 1.379(4) . ?
C6 N1 1.334(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.405(5) . ?
C8 H8 0.9300 . ?
C9 N2 1.326(4) . ?
C9 C12 1.498(4) . ?
C10 C11 1.347(6) . ?
C10 N1 1.493(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
Cu01 O2 1.891(2) 3_766 ?
Cu01 O2 1.891(2) . ?
Cu01 O1 1.925(2) 3_766 ?
Cu01 O1 1.925(2) . ?
O1W H3W 0.918(18) . ?
O1W H4W 0.925(19) . ?

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
O3 C1 O2 122.0(3) . . ?
O3 C1 C2 119.4(3) . . ?
O2 C1 C2 118.6(3) . . ?
C6 C2 C3 119.1(3) . . ?
C6 C2 C1 116.6(3) . . ?
C3 C2 C1 124.3(3) . . ?
O1 C3 C2 125.6(3) . . ?
O1 C3 C4 118.1(3) . . ?
C2 C3 C4 116.3(2) . . ?
C7 C4 C5 116.7(3) . . ?
C7 C4 C3 122.3(3) . . ?
C5 C4 C3 121.0(3) . . ?
N2 C5 N1 117.0(3) . . ?
N2 C5 C4 123.9(3) . . ?
N1 C5 C4 119.0(3) . . ?
N1 C6 C2 124.7(3) . . ?
N1 C6 H6 117.7 . . ?
C2 C6 H6 117.7 . . ?
C8 C7 C4 119.9(3) . . ?
C8 C7 H7 120.1 . . ?
C4 C7 H7 120.1 . . ?
C7 C8 C9 119.2(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
N2 C9 C8 122.4(3) . . ?
N2 C9 C12 116.9(3) . . ?
C8 C9 C12 120.7(3) . . ?
C11 C10 N1 118.5(4) . . ?
C11 C10 H10A 107.7 . . ?
N1 C10 H10A 107.7 . . ?
C11 C10 H10B 107.7 . . ?
N1 C10 H10B 107.7 . . ?
H10A C10 H10B 107.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 Cu01 O2 180.0 3_766 . ?
O2 Cu01 O1 93.36(9) 3_766 3_766 ?
O2 Cu01 O1 86.64(9) . 3_766 ?
O2 Cu01 O1 86.64(9) 3_766 . ?
O2 Cu01 O1 93.36(9) . . ?
O1 Cu01 O1 180.0 3_766 . ?
C6 N1 C5 119.7(3) . . ?
C6 N1 C10 119.0(3) . . ?
C5 N1 C10 121.3(3) . . ?
C9 N2 C5 117.8(3) . . ?
C3 O1 Cu01 125.5(2) . . ?
C1 O2 Cu01 131.2(2) . . ?
H3W O1W H4W 95(2) . . ?

_refine_diff_density_max         0.493
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.077

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

####################################################################### 
# 
# 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_V
_database_code_depnum_ccdc_archive 'CCDC 1938703'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H54 Cl2 Cu2 N8 O14'
_chemical_formula_weight         1164.97

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'
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'
H H 0.0000 0.0000 '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                   9.069(6)
_cell_length_b                   12.511(10)
_cell_length_c                   12.708(9)
_cell_angle_alpha                116.23(6)
_cell_angle_beta                 91.24(6)
_cell_angle_gamma                97.94(6)
_cell_volume                     1275.4(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    33096
_cell_measurement_theta_min      2.682
_cell_measurement_theta_max      24.999

_exptl_crystal_description       plate
_exptl_crystal_colour            blue


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             602
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.013
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.970

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5845
_exptl_absorpt_correction_T_max  0.7454

_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)


_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33096
_diffrn_reflns_av_unetI/netI     0.1479
_diffrn_reflns_av_R_equivalents  0.2823
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.682
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4491
_reflns_number_gt                1939
_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 SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 4.1.3'
_computing_publication_material  ?
_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)+(0.1279P)²] 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         4491
_refine_ls_number_parameters     343
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.2057
_refine_ls_R_factor_gt           0.0799
_refine_ls_wR_factor_ref         0.2632
_refine_ls_wR_factor_gt          0.1897
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.7736(9) 0.5891(8) 0.2372(8) 0.054(2) Uani 1 1 d . . . . .
C2 C 0.6351(9) 0.5421(7) 0.2724(7) 0.048(2) Uani 1 1 d . . . . .
C3 C 0.5241(9) 0.6125(8) 0.2987(7) 0.054(2) Uani 1 1 d . . . . .
H3 H 0.5396 0.6824 0.2888 0.065 Uiso 1 1 calc R U . . .
C4 C 0.3695(9) 0.4869(8) 0.3594(7) 0.050(2) Uani 1 1 d . . . . .
C5 C 0.4749(9) 0.4092(8) 0.3324(7) 0.050(2) Uani 1 1 d . . . . .
C6 C 0.6128(9) 0.4312(8) 0.2816(7) 0.049(2) Uani 1 1 d . . . . .
C7 C 0.2152(9) 0.3738(8) 0.4253(7) 0.055(2) Uani 1 1 d . . . . .
C8 C 0.3116(10) 0.2886(8) 0.3978(8) 0.061(2) Uani 1 1 d . . . . .
H8 H 0.2878 0.2209 0.4107 0.073 Uiso 1 1 calc R U . . .
C9 C 0.4409(10) 0.3076(8) 0.3517(7) 0.053(2) Uani 1 1 d . . . . .
H9 H 0.5069 0.2525 0.3330 0.064 Uiso 1 1 calc R U . . .
C10 C 0.2800(10) 0.6664(8) 0.3570(8) 0.064(3) Uani 1 1 d . . . . .
H10A H 0.2898 0.7014 0.3024 0.077 Uiso 1 1 calc R U . . .
H10B H 0.1804 0.6197 0.3414 0.077 Uiso 1 1 calc R U . . .
C11 C 0.3002(11) 0.7654(9) 0.4809(9) 0.083(3) Uani 1 1 d . . . . .
H11A H 0.2263 0.8164 0.4913 0.125 Uiso 1 1 calc R U . . .
H11B H 0.2890 0.7308 0.5348 0.125 Uiso 1 1 calc R U . . .
H11C H 0.3982 0.8124 0.4959 0.125 Uiso 1 1 calc R U . . .
C12 C 0.0709(10) 0.3541(9) 0.4756(9) 0.076(3) Uani 1 1 d . . . . .
H12A H 0.0653 0.2823 0.4861 0.114 Uiso 1 1 calc R U . . .
H12B H 0.0674 0.4222 0.5503 0.114 Uiso 1 1 calc R U . . .
H12C H -0.0119 0.3453 0.4225 0.114 Uiso 1 1 calc R U . . .
C13 C 1.1439(10) 0.4445(8) 0.0764(8) 0.055(2) Uani 1 1 d . . . . .
H13 H 1.0981 0.5088 0.0822 0.066 Uiso 1 1 calc R U . . .
C14 C 1.2856(10) 0.4376(9) 0.0379(8) 0.063(3) Uani 1 1 d . . . . .
H14 H 1.3338 0.4969 0.0195 0.076 Uiso 1 1 calc R U . . .
C15 C 1.3538(10) 0.3435(9) 0.0272(8) 0.064(3) Uani 1 1 d . . . . .
H15 H 1.4489 0.3381 0.0013 0.077 Uiso 1 1 calc R U . . .
C16 C 1.2798(10) 0.2547(8) 0.0556(8) 0.055(2) Uani 1 1 d . . . . .
C17 C 1.3413(11) 0.1555(9) 0.0515(9) 0.066(3) Uani 1 1 d . . . . .
H17 H 1.4355 0.1444 0.0251 0.079 Uiso 1 1 calc R U . . .
C18 C 1.2682(12) 0.0782(10) 0.0844(9) 0.075(3) Uani 1 1 d . . . . .
H18 H 1.3120 0.0139 0.0810 0.090 Uiso 1 1 calc R U . . .
C19 C 1.1212(11) 0.0914(8) 0.1255(8) 0.059(2) Uani 1 1 d . . . . .
C20 C 1.0387(12) 0.0142(9) 0.1648(8) 0.068(3) Uani 1 1 d . . . . .
H20 H 1.0779 -0.0508 0.1647 0.082 Uiso 1 1 calc R U . . .
C21 C 0.9024(13) 0.0347(9) 0.2026(9) 0.078(3) Uani 1 1 d . . . . .
H21 H 0.8473 -0.0151 0.2295 0.093 Uiso 1 1 calc R U . . .
C22 C 0.8450(11) 0.1336(8) 0.2004(8) 0.063(3) Uani 1 1 d . . . . .
H22 H 0.7503 0.1469 0.2247 0.076 Uiso 1 1 calc R U . . .
C23 C 1.0598(10) 0.1879(8) 0.1287(7) 0.052(2) Uani 1 1 d . . . . .
C24 C 1.1395(9) 0.2712(8) 0.0948(7) 0.048(2) Uani 1 1 d . . . . .
Cl1 Cl 0.7221(2) 0.2615(2) -0.0372(2) 0.0654(7) Uani 1 1 d . . . . .
Cu01 Cu 0.86824(12) 0.35746(10) 0.16312(10) 0.0574(5) Uani 1 1 d . . . . .
N1 N 0.3941(8) 0.5851(6) 0.3382(6) 0.0562(19) Uani 1 1 d . . . . .
N2 N 0.2408(7) 0.4709(6) 0.4052(6) 0.0554(19) Uani 1 1 d . . . . .
N3 N 1.0720(7) 0.3646(6) 0.1048(6) 0.0494(18) Uani 1 1 d . . . . .
N4 N 0.9218(8) 0.2074(6) 0.1650(6) 0.0519(18) Uani 1 1 d . . . . .
O1 O 0.7021(6) 0.3578(5) 0.2558(5) 0.0587(16) Uani 1 1 d . . . . .
O2 O 0.8725(6) 0.5230(5) 0.1984(5) 0.0624(17) Uani 1 1 d . . . . .
O1W O 1.0736(8) 0.8024(6) 0.2495(7) 0.091(2) Uani 1 1 d . . . . .
O3 O 0.7904(7) 0.6941(5) 0.2477(6) 0.0700(19) Uani 1 1 d . . . . .
O2W O 0.6850(11) 0.9096(7) 0.3652(7) 0.103(3) Uani 1 1 d D . . . .
O3W O 0.4851(10) 0.9759(7) 0.2537(9) 0.116(3) Uani 1 1 d D . . . .
O4W O 0.7449(10) 0.9833(7) 0.5991(8) 0.117(3) Uani 1 1 d . . . . .
H1W H 1.0154 0.7528 0.2667 0.175 Uiso 1 1 d . U . . .
H2W H 1.1008 0.7586 0.1809 0.175 Uiso 1 1 d . U . . .
H3W H 0.7227 0.8524 0.3135 0.175 Uiso 1 1 d . U . . .
H7W H 0.8090 1.0482 0.6365 0.175 Uiso 1 1 d . U . . .
H8W H 0.6595 1.0031 0.6245 0.175 Uiso 1 1 d . U . . .
H6W H 0.431(14) 0.914(8) 0.191(8) 0.175 Uiso 1 1 d D U . . .
H5W H 0.539(13) 0.934(10) 0.277(11) 0.175 Uiso 1 1 d D U . . .
H4W H 0.650(16) 0.911(14) 0.431(8) 0.175 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
C1 O3 1.246(9) . ?
C1 O2 1.263(9) . ?
C1 C2 1.476(11) . ?
C2 C3 1.378(11) . ?
C2 C6 1.430(11) . ?
C3 N1 1.351(10) . ?
C3 H3 0.9300 . ?
C4 N2 1.346(10) . ?
C4 N1 1.361(10) . ?
C4 C5 1.397(11) . ?
C5 C9 1.394(11) . ?
C5 C6 1.467(11) . ?
C6 O1 1.247(9) . ?
C7 N2 1.339(10) . ?
C7 C8 1.402(12) . ?
C7 C12 1.506(12) . ?
C8 C9 1.360(11) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.499(13) . ?
C10 N1 1.500(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N3 1.307(10) . ?
C13 C14 1.385(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.406(13) . ?
C15 H15 0.9300 . ?
C16 C24 1.385(11) . ?
C16 C17 1.410(11) . ?
C17 C18 1.320(13) . ?
C17 H17 0.9300 . ?
C18 C19 1.447(14) . ?
C18 H18 0.9300 . ?
C19 C23 1.383(11) . ?
C19 C20 1.409(13) . ?
C20 C21 1.353(13) . ?
C20 H20 0.9300 . ?
C21 C22 1.418(12) . ?
C21 H21 0.9300 . ?
C22 N4 1.320(10) . ?
C22 H22 0.9300 . ?
C23 N4 1.360(10) . ?
C23 C24 1.412(12) . ?
C24 N3 1.351(10) . ?
Cl1 Cu01 2.528(4) . ?
Cu01 O2 1.910(6) . ?
Cu01 O1 1.932(6) . ?
Cu01 N3 2.011(7) . ?
Cu01 N4 2.013(7) . ?
O1W H1W 0.863(7) . ?
O1W H2W 0.864(7) . ?
O2W H3W 0.850(7) . ?
O2W H4W 0.90(2) . ?
O3W H6W 0.90(2) . ?
O3W H5W 0.90(2) . ?
O4W H7W 0.860(8) . ?
O4W H8W 0.871(9) . ?

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
O3 C1 O2 121.7(8) . . ?
O3 C1 C2 118.8(8) . . ?
O2 C1 C2 119.4(8) . . ?
C3 C2 C6 119.9(7) . . ?
C3 C2 C1 116.2(8) . . ?
C6 C2 C1 123.9(7) . . ?
N1 C3 C2 123.4(8) . . ?
N1 C3 H3 118.3 . . ?
C2 C3 H3 118.3 . . ?
N2 C4 N1 116.2(7) . . ?
N2 C4 C5 124.0(8) . . ?
N1 C4 C5 119.8(7) . . ?
C9 C5 C4 117.1(8) . . ?
C9 C5 C6 121.4(8) . . ?
C4 C5 C6 121.4(8) . . ?
O1 C6 C2 125.8(7) . . ?
O1 C6 C5 119.4(8) . . ?
C2 C6 C5 114.7(7) . . ?
N2 C7 C8 123.7(8) . . ?
N2 C7 C12 117.1(8) . . ?
C8 C7 C12 119.1(8) . . ?
C9 C8 C7 118.2(8) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C9 C5 120.3(8) . . ?
C8 C9 H9 119.8 . . ?
C5 C9 H9 119.8 . . ?
C11 C10 N1 110.7(8) . . ?
C11 C10 H10A 109.5 . . ?
N1 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 122.7(8) . . ?
N3 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
C15 C14 C13 119.6(8) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 119.6(8) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C24 C16 C15 116.1(8) . . ?
C24 C16 C17 119.3(9) . . ?
C15 C16 C17 124.5(9) . . ?
C18 C17 C16 121.4(9) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 121.3(9) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C23 C19 C20 118.3(9) . . ?
C23 C19 C18 117.5(9) . . ?
C20 C19 C18 124.2(9) . . ?
C21 C20 C19 119.8(9) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 118.8(10) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
N4 C22 C21 122.0(9) . . ?
N4 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
N4 C23 C19 121.9(9) . . ?
N4 C23 C24 117.2(7) . . ?
C19 C23 C24 120.9(8) . . ?
N3 C24 C16 124.0(8) . . ?
N3 C24 C23 116.4(7) . . ?
C16 C24 C23 119.6(8) . . ?
O2 Cu01 O1 92.4(2) . . ?
O2 Cu01 N3 89.5(3) . . ?
O1 Cu01 N3 165.2(3) . . ?
O2 Cu01 N4 161.3(3) . . ?
O1 Cu01 N4 92.0(3) . . ?
N3 Cu01 N4 81.8(3) . . ?
O2 Cu01 Cl1 98.5(2) . . ?
O1 Cu01 Cl1 97.9(2) . . ?
N3 Cu01 Cl1 96.3(2) . . ?
N4 Cu01 Cl1 98.9(2) . . ?
C3 N1 C4 120.4(7) . . ?
C3 N1 C10 117.6(7) . . ?
C4 N1 C10 122.1(7) . . ?
C7 N2 C4 116.5(7) . . ?
C13 N3 C24 117.9(7) . . ?
C13 N3 Cu01 129.3(6) . . ?
C24 N3 Cu01 112.7(6) . . ?
C22 N4 C23 119.3(8) . . ?
C22 N4 Cu01 128.8(6) . . ?
C23 N4 Cu01 111.8(6) . . ?
C6 O1 Cu01 124.2(5) . . ?
C1 O2 Cu01 129.9(6) . . ?
H1W O1W H2W 105.3(7) . . ?
H3W O2W H4W 125(10) . . ?
H6W O3W H5W 99(3) . . ?
H7W O4W H8W 104.9(9) . . ?

_refine_diff_density_max         0.889
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.108

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

####################################################################### 
# 
# 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_IV
_database_code_depnum_ccdc_archive 'CCDC 1938702'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;CQE, Instituto Superior Tecnico, IST ID
Portugal
;
_audit_update_record             
;
2019-09-23 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H42 Cl2 Cu2 N8 O8'
_chemical_formula_weight         528.45

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                   8.998(3)
_cell_length_b                   19.758(5)
_cell_length_c                   12.654(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.021(9)
_cell_angle_gamma                90
_cell_volume                     2227.6(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3841
_cell_measurement_theta_min      2.508
_cell_measurement_theta_max      24.997

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_F_000             1084
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.141
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.956

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5131
_exptl_absorpt_correction_T_max  0.7454

_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)


_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28999
_diffrn_reflns_av_unetI/netI     0.1174
_diffrn_reflns_av_R_equivalents  0.2160
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.508
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3841
_reflns_number_gt                1900
_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 SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 4.1.3'
_computing_publication_material  ?
_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)+(0.1080P)²] 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         3841
_refine_ls_number_parameters     313
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1660
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.2084
_refine_ls_wR_factor_gt          0.1543
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.2879(9) 0.7110(3) 0.6290(6) 0.0453(18) Uani 1 1 d . . . . .
C2 C 0.4081(9) 0.6588(3) 0.6184(5) 0.0435(18) Uani 1 1 d . . . . .
C3 C 0.4024(9) 0.5903(3) 0.6554(5) 0.0404(17) Uani 1 1 d . . . . .
C4 C 0.5254(8) 0.5479(3) 0.6342(5) 0.0366(16) Uani 1 1 d . . . . .
C5 C 0.6461(9) 0.5722(3) 0.5865(5) 0.0418(17) Uani 1 1 d . . . . .
C6 C 0.5301(10) 0.6792(3) 0.5728(6) 0.0478(19) Uani 1 1 d . . . . .
H6 H 0.5329 0.7242 0.5519 0.057 Uiso 1 1 calc R U . . .
C7 C 0.5345(9) 0.4802(3) 0.6653(5) 0.0433(18) Uani 1 1 d . . . . .
H7 H 0.4615 0.4616 0.7018 0.052 Uiso 1 1 calc R U . . .
C8 C 0.6507(9) 0.4412(3) 0.6420(6) 0.0482(19) Uani 1 1 d . . . . .
H8 H 0.6542 0.3954 0.6592 0.058 Uiso 1 1 calc R U . . .
C9 C 0.7645(9) 0.4704(4) 0.5923(5) 0.0484(19) Uani 1 1 d . . . . .
C10 C 0.7722(9) 0.6687(4) 0.5067(6) 0.050(2) Uani 1 1 d . . . . .
H10A H 0.8651 0.6475 0.5383 0.060 Uiso 1 1 calc R U . . .
H10B H 0.7799 0.7168 0.5217 0.060 Uiso 1 1 calc R U . . .
C11 C 0.7511(10) 0.6578(4) 0.3882(6) 0.067(2) Uani 1 1 d . . . . .
H11A H 0.8346 0.6768 0.3589 0.100 Uiso 1 1 calc R U . . .
H11B H 0.7452 0.6101 0.3733 0.100 Uiso 1 1 calc R U . . .
H11C H 0.6601 0.6794 0.3567 0.100 Uiso 1 1 calc R U . . .
C12 C 0.8941(10) 0.4284(4) 0.5668(7) 0.062(2) Uani 1 1 d . . . . .
H12A H 0.8823 0.3826 0.5898 0.093 Uiso 1 1 calc R U . . .
H12B H 0.8966 0.4290 0.4912 0.093 Uiso 1 1 calc R U . . .
H12C H 0.9861 0.4466 0.6032 0.093 Uiso 1 1 calc R U . . .
C13 C -0.1086(10) 0.7169(4) 0.7740(6) 0.051(2) Uani 1 1 d . . . . .
H13 H -0.0538 0.7495 0.7429 0.062 Uiso 1 1 calc R U . . .
C14 C -0.2448(10) 0.7352(4) 0.8037(6) 0.059(2) Uani 1 1 d . . . . .
H14 H -0.2787 0.7794 0.7932 0.071 Uiso 1 1 calc R U . . .
C15 C -0.3307(10) 0.6890(4) 0.8483(6) 0.055(2) Uani 1 1 d . . . . .
H15 H -0.4230 0.7011 0.8678 0.066 Uiso 1 1 calc R U . . .
C16 C -0.2753(8) 0.6222(3) 0.8641(5) 0.0416(17) Uani 1 1 d . . . . .
C17 C -0.3538(10) 0.5690(4) 0.9090(6) 0.057(2) Uani 1 1 d . . . . .
H17 H -0.4461 0.5780 0.9310 0.069 Uiso 1 1 calc R U . . .
C18 C -0.2960(9) 0.5056(4) 0.9200(6) 0.053(2) Uani 1 1 d . . . . .
H18 H -0.3504 0.4716 0.9478 0.064 Uiso 1 1 calc R U . . .
C19 C -0.1517(9) 0.4902(3) 0.8891(5) 0.0441(18) Uani 1 1 d . . . . .
C20 C -0.0824(10) 0.4262(4) 0.8985(6) 0.055(2) Uani 1 1 d . . . . .
H20 H -0.1305 0.3899 0.9260 0.066 Uiso 1 1 calc R U . . .
C21 C 0.0545(10) 0.4176(4) 0.8674(6) 0.057(2) Uani 1 1 d . . . . .
H21 H 0.1003 0.3753 0.8732 0.068 Uiso 1 1 calc R U . . .
C22 C 0.1269(10) 0.4722(3) 0.8265(6) 0.052(2) Uani 1 1 d . . . . .
H22 H 0.2218 0.4657 0.8070 0.062 Uiso 1 1 calc R U . . .
C23 C -0.0730(9) 0.5419(3) 0.8465(5) 0.0424(18) Uani 1 1 d . . . . .
C24 C -0.1345(9) 0.6084(3) 0.8324(5) 0.0416(17) Uani 1 1 d . . . . .
Cl1 Cl 0.2960(2) 0.65940(9) 0.92732(16) 0.0559(6) Uani 1 1 d . . . . .
Cu01 Cu 0.14647(11) 0.61798(4) 0.75832(7) 0.0467(3) Uani 1 1 d . . . . .
N1 N 0.6454(7) 0.6400(3) 0.5557(4) 0.0448(15) Uani 1 1 d . . . . .
N2 N 0.7628(7) 0.5352(3) 0.5658(4) 0.0429(14) Uani 1 1 d . . . . .
N3 N -0.0519(7) 0.6543(3) 0.7878(4) 0.0394(14) Uani 1 1 d . . . . .
N4 N 0.0653(7) 0.5329(3) 0.8148(4) 0.0424(14) Uani 1 1 d . . . . .
O1 O 0.3016(6) 0.5660(2) 0.7035(4) 0.0499(13) Uani 1 1 d . . . . .
O2 O 0.1719(6) 0.6931(2) 0.6678(4) 0.0582(15) Uani 1 1 d . . . . .
O1W O 0.0457(8) 0.8519(3) 0.6436(5) 0.0755(18) Uani 1 1 d D . . . .
O3 O 0.3045(7) 0.7684(3) 0.5955(5) 0.0697(17) Uani 1 1 d . . . . .
H1W H -0.036(7) 0.858(5) 0.596(6) 0.105 Uiso 1 1 d D U . . .
H2W H 0.124(7) 0.826(4) 0.634(8) 0.105 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
C1 O3 1.227(8) . ?
C1 O2 1.264(9) . ?
C1 C2 1.514(10) . ?
C2 C6 1.370(10) . ?
C2 C3 1.434(9) . ?
C3 O1 1.256(8) . ?
C3 C4 1.443(9) . ?
C4 C7 1.394(8) . ?
C4 C5 1.399(9) . ?
C5 N2 1.336(9) . ?
C5 N1 1.394(8) . ?
C6 N1 1.336(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.364(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.400(10) . ?
C8 H8 0.9300 . ?
C9 N2 1.323(8) . ?
C9 C12 1.502(10) . ?
C10 N1 1.485(9) . ?
C10 C11 1.501(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N3 1.340(9) . ?
C13 C14 1.379(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.415(10) . ?
C15 H15 0.9300 . ?
C16 C24 1.408(10) . ?
C16 C17 1.426(10) . ?
C17 C18 1.356(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.440(10) . ?
C18 H18 0.9300 . ?
C19 C23 1.392(9) . ?
C19 C20 1.408(10) . ?
C20 C21 1.355(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.397(10) . ?
C21 H21 0.9300 . ?
C22 N4 1.320(8) . ?
C22 H22 0.9300 . ?
C23 N4 1.372(9) . ?
C23 C24 1.428(9) . ?
C24 N3 1.346(8) . ?
Cl1 Cu01 2.500(2) . ?
Cu01 O2 1.908(5) . ?
Cu01 O1 1.937(5) . ?
Cu01 N4 2.004(5) . ?
Cu01 N3 2.006(6) . ?
O1W H1W 0.89(2) . ?
O1W H2W 0.89(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
O3 C1 O2 122.6(7) . . ?
O3 C1 C2 118.4(7) . . ?
O2 C1 C2 118.9(6) . . ?
C6 C2 C3 118.8(7) . . ?
C6 C2 C1 117.5(6) . . ?
C3 C2 C1 123.7(7) . . ?
O1 C3 C2 125.4(7) . . ?
O1 C3 C4 119.5(6) . . ?
C2 C3 C4 115.0(6) . . ?
C7 C4 C5 115.6(6) . . ?
C7 C4 C3 121.4(6) . . ?
C5 C4 C3 122.9(6) . . ?
N2 C5 N1 116.4(6) . . ?
N2 C5 C4 125.1(6) . . ?
N1 C5 C4 118.4(6) . . ?
N1 C6 C2 125.7(6) . . ?
N1 C6 H6 117.2 . . ?
C2 C6 H6 117.2 . . ?
C8 C7 C4 119.9(6) . . ?
C8 C7 H7 120.0 . . ?
C4 C7 H7 120.0 . . ?
C7 C8 C9 119.7(6) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
N2 C9 C8 122.0(7) . . ?
N2 C9 C12 117.5(7) . . ?
C8 C9 C12 120.5(7) . . ?
N1 C10 C11 111.4(7) . . ?
N1 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 122.9(7) . . ?
N3 C13 H13 118.6 . . ?
C14 C13 H13 118.6 . . ?
C15 C14 C13 120.9(7) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 118.2(7) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C24 C16 C15 117.0(6) . . ?
C24 C16 C17 119.1(6) . . ?
C15 C16 C17 124.0(7) . . ?
C18 C17 C16 121.1(7) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 121.0(7) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C23 C19 C20 116.6(7) . . ?
C23 C19 C18 118.4(7) . . ?
C20 C19 C18 124.9(7) . . ?
C21 C20 C19 119.8(7) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.1(7) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
N4 C22 C21 122.2(7) . . ?
N4 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
N4 C23 C19 123.3(6) . . ?
N4 C23 C24 115.7(6) . . ?
C19 C23 C24 120.9(7) . . ?
N3 C24 C16 124.1(6) . . ?
N3 C24 C23 116.5(6) . . ?
C16 C24 C23 119.4(6) . . ?
O2 Cu01 O1 92.5(2) . . ?
O2 Cu01 N4 161.2(3) . . ?
O1 Cu01 N4 90.0(2) . . ?
O2 Cu01 N3 91.0(2) . . ?
O1 Cu01 N3 163.8(2) . . ?
N4 Cu01 N3 81.7(2) . . ?
O2 Cu01 Cl1 99.43(18) . . ?
O1 Cu01 Cl1 98.67(17) . . ?
N4 Cu01 Cl1 98.57(17) . . ?
N3 Cu01 Cl1 96.32(17) . . ?
C6 N1 C5 119.0(6) . . ?
C6 N1 C10 120.4(6) . . ?
C5 N1 C10 120.6(6) . . ?
C9 N2 C5 117.5(6) . . ?
C13 N3 C24 117.0(6) . . ?
C13 N3 Cu01 129.7(5) . . ?
C24 N3 Cu01 113.2(4) . . ?
C22 N4 C23 117.9(6) . . ?
C22 N4 Cu01 129.3(5) . . ?
C23 N4 Cu01 112.8(4) . . ?
C3 O1 Cu01 125.2(4) . . ?
C1 O2 Cu01 128.7(5) . . ?
H1W O1W H2W 125(9) . . ?

_refine_diff_density_max         0.809
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.099

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

