# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1965359'
loop_
_audit_author_name
_audit_author_address
'Santiago Gomez Ruiz'
;University of Rey Juan Carlos 
Spain
;
_audit_update_record             
;
2020-09-18 deposited with the CCDC.	2020-10-26 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         ?
_chemical_formula_sum            'C30 H30 Cu N4 O13'
_chemical_formula_weight         718.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   7.1549(6)
_cell_length_b                   13.9178(9)
_cell_length_c                   16.9211(12)
_cell_angle_alpha                110.138(2)
_cell_angle_beta                 100.826(3)
_cell_angle_gamma                91.382(2)
_cell_volume                     1546.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6444
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      26.42

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             742
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.782
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5379
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.9433.
The λ/2 correction factor is 0.00150. 
In addition, two disordered water molecules were removed using 
the program SQUEEZED implemented in Platon
;
_exptl_absorpt_special_details   
;
Squeezed: A.L. Spek, Acta Cryst C 2015, 71, 9-18
;
_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 D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26494
_diffrn_reflns_av_unetI/netI     0.0914
_diffrn_reflns_av_R_equivalents  0.1127
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         26.441
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6347
_reflns_number_gt                4776
_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 ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0594P)²+2.8972P] 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         6347
_refine_ls_number_parameters     434
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.06735(6) 0.40468(3) 0.83218(2) 0.01373(13) Uani 1 1 d . . . . .
O1 O -0.1349(3) 0.46772(16) 0.77795(14) 0.0169(5) Uani 1 1 d . . . . .
O2 O 0.0386(4) 0.5163(2) 0.69907(18) 0.0309(6) Uani 1 1 d . . . . .
O3 O -0.2922(4) 0.5294(2) 0.50103(16) 0.0349(7) Uani 1 1 d . . . . .
O4 O -0.1665(4) 0.74347(19) 0.78195(16) 0.0307(6) Uani 1 1 d . . . . .
O5 O -0.0209(3) 0.27234(16) 0.74054(14) 0.0184(5) Uani 1 1 d D . . . .
O6 O 0.3175(3) 0.43956(17) 0.77915(14) 0.0198(5) Uani 1 1 d D . . . .
O7 O 0.4378(4) 0.26101(16) 0.69082(16) 0.0249(6) Uani 1 1 d . . . . .
O8 O 0.2283(3) 0.14195(16) 0.69492(15) 0.0222(5) Uani 1 1 d . . . . .
O9 O 0.5402(4) 0.05683(17) 0.82078(15) 0.0295(6) Uani 1 1 d . . . . .
O10 O 0.3879(4) -0.10205(17) 0.52943(14) 0.0261(6) Uani 1 1 d . . . . .
N1 N 0.1847(4) 0.33958(19) 0.91705(17) 0.0154(6) Uani 1 1 d . . . . .
N2 N 0.1549(4) 0.53169(19) 0.93479(16) 0.0146(6) Uani 1 1 d . . . . .
N3 N -0.2529(4) 0.6187(2) 0.64760(17) 0.0189(6) Uani 1 1 d . . . . .
N4 N 0.4809(4) -0.00207(19) 0.67273(17) 0.0160(6) Uani 1 1 d . . . . .
C1 C 0.1842(5) 0.2386(2) 0.9023(2) 0.0210(7) Uani 1 1 d . . . . .
H1 H 0.133303 0.191119 0.845983 0.025 Uiso 1 1 calc R U . . .
C2 C 0.2554(5) 0.2016(3) 0.9667(2) 0.0256(8) Uani 1 1 d . . . . .
H2 H 0.253477 0.129642 0.954905 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3296(5) 0.2707(3) 1.0487(2) 0.0258(8) Uani 1 1 d . . . . .
H3 H 0.377165 0.246787 1.094219 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3338(5) 0.3755(3) 1.0638(2) 0.0211(7) Uani 1 1 d . . . . .
H4 H 0.387078 0.424169 1.119338 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2593(4) 0.4078(2) 0.9967(2) 0.0154(7) Uani 1 1 d . . . . .
C6 C 0.2487(4) 0.5173(2) 1.0064(2) 0.0143(6) Uani 1 1 d . . . . .
C7 C 0.3258(5) 0.5990(3) 1.0819(2) 0.0206(7) Uani 1 1 d . . . . .
H7 H 0.387508 0.587177 1.132073 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3102(5) 0.6981(2) 1.0821(2) 0.0242(8) Uani 1 1 d . . . . .
H8 H 0.364020 0.755382 1.132318 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2156(5) 0.7133(2) 1.0084(2) 0.0228(8) Uani 1 1 d . . . . .
H9 H 0.203210 0.780744 1.007601 0.027 Uiso 1 1 calc R U . . .
C10 C 0.1399(5) 0.6283(2) 0.9362(2) 0.0182(7) Uani 1 1 d . . . . .
H10 H 0.074836 0.638530 0.885803 0.022 Uiso 1 1 calc R U . . .
C11 C -0.1131(5) 0.5044(2) 0.7201(2) 0.0164(7) Uani 1 1 d . . . . .
C12 C -0.2943(5) 0.5357(2) 0.6764(2) 0.0215(7) Uani 1 1 d . . . . .
H12A H -0.360584 0.475705 0.626454 0.026 Uiso 1 1 calc R U . . .
H12B H -0.381083 0.557498 0.717224 0.026 Uiso 1 1 calc R U . . .
C13 C -0.2542(5) 0.6077(3) 0.5614(2) 0.0218(7) Uani 1 1 d . . . . .
C14 C -0.1930(5) 0.7131(3) 0.5653(2) 0.0222(7) Uani 1 1 d . . . . .
C15 C -0.1727(6) 0.7472(3) 0.4994(3) 0.0353(10) Uani 1 1 d . . . . .
H15 H -0.198524 0.702178 0.441014 0.042 Uiso 1 1 calc R U . . .
C16 C -0.1123(6) 0.8515(3) 0.5232(3) 0.0399(11) Uani 1 1 d . . . . .
H16 H -0.098277 0.878136 0.479712 0.048 Uiso 1 1 calc R U . . .
C17 C -0.0727(6) 0.9161(3) 0.6074(3) 0.0388(10) Uani 1 1 d . . . . .
H17 H -0.030089 0.986170 0.620885 0.047 Uiso 1 1 calc R U . . .
C18 C -0.0934(5) 0.8819(3) 0.6742(3) 0.0280(8) Uani 1 1 d . . . . .
H18 H -0.066227 0.926762 0.732699 0.034 Uiso 1 1 calc R U . . .
C19 C -0.1558(5) 0.7788(3) 0.6503(2) 0.0213(7) Uani 1 1 d . . . . .
C20 C -0.1887(5) 0.7175(2) 0.7038(2) 0.0189(7) Uani 1 1 d . . . . .
C21 C 0.3855(5) 0.1715(2) 0.68525(19) 0.0173(7) Uani 1 1 d . . . . .
C22 C 0.5319(5) 0.0945(2) 0.6636(2) 0.0184(7) Uani 1 1 d . . . . .
H22A H 0.545282 0.080881 0.603623 0.022 Uiso 1 1 calc R U . . .
H22B H 0.657496 0.124869 0.701909 0.022 Uiso 1 1 calc R U . . .
C23 C 0.4844(5) -0.0125(2) 0.7515(2) 0.0169(7) Uani 1 1 d . . . . .
C24 C 0.4104(5) -0.1202(2) 0.7324(2) 0.0157(7) Uani 1 1 d . . . . .
C25 C 0.3807(5) -0.1710(2) 0.7867(2) 0.0215(7) Uani 1 1 d . . . . .
H25 H 0.406208 -0.136955 0.847351 0.026 Uiso 1 1 calc R U . . .
C26 C 0.3115(5) -0.2746(2) 0.7485(2) 0.0217(7) Uani 1 1 d . . . . .
H26 H 0.286353 -0.311672 0.783757 0.026 Uiso 1 1 calc R U . . .
C27 C 0.2786(5) -0.3248(2) 0.6596(2) 0.0199(7) Uani 1 1 d . . . . .
H27 H 0.236158 -0.396107 0.635604 0.024 Uiso 1 1 calc R U . . .
C28 C 0.3067(5) -0.2726(2) 0.6054(2) 0.0187(7) Uani 1 1 d . . . . .
H28 H 0.282264 -0.306454 0.544674 0.022 Uiso 1 1 calc R U . . .
C29 C 0.3710(5) -0.1701(2) 0.6430(2) 0.0163(7) Uani 1 1 d . . . . .
C30 C 0.4111(5) -0.0929(2) 0.6047(2) 0.0155(7) Uani 1 1 d . . . . .
O2W O -0.2777(3) 0.28591(17) 0.61082(15) 0.0213(5) Uiso 1 1 d D . . . .
H5OA H 0.066(4) 0.226(2) 0.717(2) 0.038(12) Uiso 1 1 d D . . . .
H5OB H -0.091(4) 0.284(3) 0.6930(17) 0.032(11) Uiso 1 1 d D . . . .
H6OA H 0.239(5) 0.467(3) 0.745(2) 0.042(12) Uiso 1 1 d D . . . .
H6OB H 0.354(8) 0.379(3) 0.746(3) 0.11(2) Uiso 1 1 d D . . . .
H2AW H -0.383(4) 0.285(3) 0.634(2) 0.025(10) Uiso 1 1 d D . . . .
H2BW H -0.295(6) 0.225(3) 0.561(2) 0.078(17) 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 O5 1.951(2) . ?
Cu1 O1 1.955(2) . ?
Cu1 N2 1.989(3) . ?
Cu1 N1 2.017(3) . ?
Cu1 O6 2.260(2) . ?
O1 C11 1.280(4) . ?
O2 C11 1.229(4) . ?
O3 C13 1.191(4) . ?
O4 C20 1.222(4) . ?
O5 H5OA 0.945(18) . ?
O5 H5OB 0.932(18) . ?
O6 H6OA 0.922(18) . ?
O6 H6OB 0.915(19) . ?
O7 C21 1.258(4) . ?
O8 C21 1.247(4) . ?
O9 C23 1.221(4) . ?
O10 C30 1.213(4) . ?
N1 C1 1.341(4) . ?
N1 C5 1.352(4) . ?
N2 C10 1.343(4) . ?
N2 C6 1.351(4) . ?
N3 C20 1.383(4) . ?
N3 C13 1.411(4) . ?
N3 C12 1.445(4) . ?
N4 C30 1.388(4) . ?
N4 C23 1.385(4) . ?
N4 C22 1.450(4) . ?
C1 C2 1.379(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.481(4) . ?
C6 C7 1.391(4) . ?
C7 C8 1.385(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.519(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.497(5) . ?
C14 C15 1.382(5) . ?
C14 C19 1.385(5) . ?
C15 C16 1.399(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.369(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.399(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.485(4) . ?
C21 C22 1.520(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.482(4) . ?
C24 C25 1.379(4) . ?
C24 C29 1.399(4) . ?
C25 C26 1.395(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.393(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.390(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.373(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.480(4) . ?
O2W H2AW 0.918(17) . ?
O2W H2BW 0.947(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Cu1 O1 89.61(9) . . ?
O5 Cu1 N2 173.60(10) . . ?
O1 Cu1 N2 94.22(10) . . ?
O5 Cu1 N1 93.24(10) . . ?
O1 Cu1 N1 154.60(10) . . ?
N2 Cu1 N1 81.11(10) . . ?
O5 Cu1 O6 95.74(9) . . ?
O1 Cu1 O6 101.39(9) . . ?
N2 Cu1 O6 88.53(9) . . ?
N1 Cu1 O6 103.42(10) . . ?
C11 O1 Cu1 122.7(2) . . ?
Cu1 O5 H5OA 122(2) . . ?
Cu1 O5 H5OB 109(2) . . ?
H5OA O5 H5OB 104(2) . . ?
Cu1 O6 H6OA 90(3) . . ?
Cu1 O6 H6OB 108(4) . . ?
H6OA O6 H6OB 110(3) . . ?
C1 N1 C5 119.6(3) . . ?
C1 N1 Cu1 126.3(2) . . ?
C5 N1 Cu1 114.0(2) . . ?
C10 N2 C6 118.7(3) . . ?
C10 N2 Cu1 125.4(2) . . ?
C6 N2 Cu1 115.7(2) . . ?
C20 N3 C13 112.0(3) . . ?
C20 N3 C12 122.7(3) . . ?
C13 N3 C12 124.9(3) . . ?
C30 N4 C23 111.7(3) . . ?
C30 N4 C22 124.7(3) . . ?
C23 N4 C22 123.4(3) . . ?
N1 C1 C2 121.9(3) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 121.3(3) . . ?
N1 C5 C6 115.2(3) . . ?
C4 C5 C6 123.5(3) . . ?
N2 C6 C7 122.2(3) . . ?
N2 C6 C5 113.9(3) . . ?
C7 C6 C5 123.9(3) . . ?
C8 C7 C6 118.3(3) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 118.7(3) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N2 C10 C9 122.4(3) . . ?
N2 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
O2 C11 O1 125.7(3) . . ?
O2 C11 C12 119.4(3) . . ?
O1 C11 C12 114.9(3) . . ?
N3 C12 C11 111.4(3) . . ?
N3 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
N3 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
O3 C13 N3 125.7(3) . . ?
O3 C13 C14 129.5(3) . . ?
N3 C13 C14 104.8(3) . . ?
C15 C14 C19 121.7(3) . . ?
C15 C14 C13 129.6(3) . . ?
C19 C14 C13 108.7(3) . . ?
C14 C15 C16 116.5(4) . . ?
C14 C15 H15 121.7 . . ?
C16 C15 H15 121.7 . . ?
C17 C16 C15 121.7(4) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 121.9(4) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C19 C18 C17 116.2(4) . . ?
C19 C18 H18 121.9 . . ?
C17 C18 H18 121.9 . . ?
C14 C19 C18 121.9(3) . . ?
C14 C19 C20 107.7(3) . . ?
C18 C19 C20 130.3(3) . . ?
O4 C20 N3 123.5(3) . . ?
O4 C20 C19 129.9(3) . . ?
N3 C20 C19 106.7(3) . . ?
O8 C21 O7 126.3(3) . . ?
O8 C21 C22 118.9(3) . . ?
O7 C21 C22 114.7(3) . . ?
N4 C22 C21 112.9(3) . . ?
N4 C22 H22A 109.0 . . ?
C21 C22 H22A 109.0 . . ?
N4 C22 H22B 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
O9 C23 N4 124.0(3) . . ?
O9 C23 C24 129.7(3) . . ?
N4 C23 C24 106.4(3) . . ?
C25 C24 C29 121.4(3) . . ?
C25 C24 C23 130.7(3) . . ?
C29 C24 C23 107.8(3) . . ?
C24 C25 C26 117.0(3) . . ?
C24 C25 H25 121.5 . . ?
C26 C25 H25 121.5 . . ?
C27 C26 C25 121.3(3) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C28 C27 C26 121.2(3) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C29 C28 C27 117.3(3) . . ?
C29 C28 H28 121.3 . . ?
C27 C28 H28 121.3 . . ?
C28 C29 C24 121.6(3) . . ?
C28 C29 C30 131.0(3) . . ?
C24 C29 C30 107.4(3) . . ?
O10 C30 N4 124.0(3) . . ?
O10 C30 C29 129.3(3) . . ?
N4 C30 C29 106.6(3) . . ?
H2AW O2W H2BW 106(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 1.0(5) . . . . ?
Cu1 N1 C1 C2 -174.8(3) . . . . ?
N1 C1 C2 C3 -0.1(5) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C1 N1 C5 C4 -0.6(5) . . . . ?
Cu1 N1 C5 C4 175.7(2) . . . . ?
C1 N1 C5 C6 -178.7(3) . . . . ?
Cu1 N1 C5 C6 -2.3(3) . . . . ?
C3 C4 C5 N1 -0.6(5) . . . . ?
C3 C4 C5 C6 177.2(3) . . . . ?
C10 N2 C6 C7 1.6(5) . . . . ?
Cu1 N2 C6 C7 177.1(2) . . . . ?
C10 N2 C6 C5 -178.9(3) . . . . ?
Cu1 N2 C6 C5 -3.5(3) . . . . ?
N1 C5 C6 N2 3.8(4) . . . . ?
C4 C5 C6 N2 -174.2(3) . . . . ?
N1 C5 C6 C7 -176.7(3) . . . . ?
C4 C5 C6 C7 5.3(5) . . . . ?
N2 C6 C7 C8 -2.1(5) . . . . ?
C5 C6 C7 C8 178.5(3) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C6 N2 C10 C9 -0.5(5) . . . . ?
Cu1 N2 C10 C9 -175.4(2) . . . . ?
C8 C9 C10 N2 -0.1(5) . . . . ?
Cu1 O1 C11 O2 -9.3(4) . . . . ?
Cu1 O1 C11 C12 171.37(19) . . . . ?
C20 N3 C12 C11 -69.6(4) . . . . ?
C13 N3 C12 C11 104.0(4) . . . . ?
O2 C11 C12 N3 -28.5(4) . . . . ?
O1 C11 C12 N3 150.9(3) . . . . ?
C20 N3 C13 O3 175.3(3) . . . . ?
C12 N3 C13 O3 1.2(6) . . . . ?
C20 N3 C13 C14 -3.0(4) . . . . ?
C12 N3 C13 C14 -177.1(3) . . . . ?
O3 C13 C14 C15 3.0(7) . . . . ?
N3 C13 C14 C15 -178.7(4) . . . . ?
O3 C13 C14 C19 -177.1(4) . . . . ?
N3 C13 C14 C19 1.1(4) . . . . ?
C19 C14 C15 C16 0.2(6) . . . . ?
C13 C14 C15 C16 180.0(4) . . . . ?
C14 C15 C16 C17 0.8(6) . . . . ?
C15 C16 C17 C18 -1.0(6) . . . . ?
C16 C17 C18 C19 0.1(6) . . . . ?
C15 C14 C19 C18 -1.1(6) . . . . ?
C13 C14 C19 C18 179.1(3) . . . . ?
C15 C14 C19 C20 -179.2(3) . . . . ?
C13 C14 C19 C20 1.0(4) . . . . ?
C17 C18 C19 C14 0.9(5) . . . . ?
C17 C18 C19 C20 178.5(3) . . . . ?
C13 N3 C20 O4 -176.2(3) . . . . ?
C12 N3 C20 O4 -1.9(5) . . . . ?
C13 N3 C20 C19 3.6(4) . . . . ?
C12 N3 C20 C19 177.9(3) . . . . ?
C14 C19 C20 O4 177.1(4) . . . . ?
C18 C19 C20 O4 -0.8(6) . . . . ?
C14 C19 C20 N3 -2.8(4) . . . . ?
C18 C19 C20 N3 179.3(3) . . . . ?
C30 N4 C22 C21 105.0(3) . . . . ?
C23 N4 C22 C21 -70.5(4) . . . . ?
O8 C21 C22 N4 -10.9(4) . . . . ?
O7 C21 C22 N4 169.7(3) . . . . ?
C30 N4 C23 O9 179.9(3) . . . . ?
C22 N4 C23 O9 -4.1(5) . . . . ?
C30 N4 C23 C24 0.2(4) . . . . ?
C22 N4 C23 C24 176.2(3) . . . . ?
O9 C23 C24 C25 1.5(6) . . . . ?
N4 C23 C24 C25 -178.8(3) . . . . ?
O9 C23 C24 C29 -178.1(3) . . . . ?
N4 C23 C24 C29 1.6(4) . . . . ?
C29 C24 C25 C26 0.7(5) . . . . ?
C23 C24 C25 C26 -178.9(3) . . . . ?
C24 C25 C26 C27 1.5(5) . . . . ?
C25 C26 C27 C28 -2.4(5) . . . . ?
C26 C27 C28 C29 1.0(5) . . . . ?
C27 C28 C29 C24 1.1(5) . . . . ?
C27 C28 C29 C30 -178.6(3) . . . . ?
C25 C24 C29 C28 -2.0(5) . . . . ?
C23 C24 C29 C28 177.6(3) . . . . ?
C25 C24 C29 C30 177.7(3) . . . . ?
C23 C24 C29 C30 -2.6(4) . . . . ?
C23 N4 C30 O10 177.2(3) . . . . ?
C22 N4 C30 O10 1.3(5) . . . . ?
C23 N4 C30 C29 -1.8(4) . . . . ?
C22 N4 C30 C29 -177.7(3) . . . . ?
C28 C29 C30 O10 3.5(6) . . . . ?
C24 C29 C30 O10 -176.2(3) . . . . ?
C28 C29 C30 N4 -177.5(3) . . . . ?
C24 C29 C30 N4 2.8(3) . . . . ?

_refine_diff_density_max         0.551
_refine_diff_density_min         -0.977
_refine_diff_density_rms         0.096


# start Validation Reply Form
_vrf_PLAT043_shelx               
;
PROBLEM: Calculated and Reported Mol. Weight Differ by .. 36.02 Check
RESPONSE: This is a consequence of the elimination of two solvent
water molecules of the assymetric unit by using the program SQUEEZED 
as suggested by the reviewer of the manuscript
;
_vrf_PLAT601_shelx               
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of . 115 Ang**3
RESPONSE: This is because of the elimination of two solvent
water molecules of the assymetric unit by using the program SQUEEZED 
as suggested by the reviewer of the manuscript
;
# end Validation Reply Form
####################################################################### 
# 
# 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 1965360'
loop_
_audit_author_name
_audit_author_address
'Santiago Gomez Ruiz'
;University of Rey Juan Carlos 
Spain
;
_audit_update_record             
;
2020-09-18 deposited with the CCDC.	2020-10-26 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         ?
_chemical_formula_sum            'C30 H26 N4 O12 Zn'
_chemical_formula_weight         699.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Zn Zn 0.2839 1.4301 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   32.858(3)
_cell_length_b                   12.1027(10)
_cell_length_c                   7.3119(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.642(4)
_cell_angle_gamma                90
_cell_volume                     2898.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4307
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.30

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.923
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.583
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.9433.
The λ/2 correction factor is 0.00150.
;
_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 D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21318
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_av_R_equivalents  0.1268
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.488
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2985
_reflns_number_gt                2370
_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 ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0381P)²+52.0667P] 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         2985
_refine_ls_number_parameters     216
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.1850
_refine_ls_wR_factor_gt          0.1750
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_restrained_S_all      1.185
_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
Zn1 Zn 0.500000 0.22277(7) 1.250000 0.0081(2) Uani 1 2 d S T P . .
O1 O 0.44345(11) 0.1099(3) 0.7059(6) 0.0151(9) Uani 1 1 d . . . . .
O2 O 0.39431(12) 0.1627(4) 0.4950(6) 0.0210(10) Uani 1 1 d . . . . .
O3 O 0.32699(13) 0.3019(4) 0.8732(7) 0.0249(10) Uani 1 1 d . . . . .
O4 O 0.32032(13) -0.0379(4) 0.6003(7) 0.0253(10) Uani 1 1 d . . . . .
O5 O 0.49770(11) 0.2079(3) 0.9598(5) 0.0115(8) Uiso 1 1 d . . . . .
O6 O 0.44862(12) 0.1168(3) 1.2411(6) 0.0150(9) Uani 1 1 d D . . . .
N1 N 0.45941(13) 0.3629(4) 1.2210(6) 0.0090(9) Uani 1 1 d . . . . .
N2 N 0.33420(14) 0.1316(4) 0.7373(7) 0.0161(11) Uani 1 1 d . . . . .
C1 C 0.47737(15) 0.4624(4) 1.2307(7) 0.0096(11) Uani 1 1 d . . . . .
C2 C 0.45523(18) 0.5595(5) 1.2033(10) 0.0220(14) Uani 1 1 d . . . . .
H2 H 0.468524 0.629247 1.212250 0.026 Uiso 1 1 calc R U . . .
C3 C 0.41289(19) 0.5528(5) 1.1621(10) 0.0234(14) Uani 1 1 d . . . . .
H3 H 0.396909 0.617840 1.143582 0.028 Uiso 1 1 calc R U . . .
C4 C 0.39495(19) 0.4500(5) 1.1491(9) 0.0214(13) Uani 1 1 d . . . . .
H4 H 0.366422 0.443110 1.118073 0.026 Uiso 1 1 calc R U . . .
C5 C 0.41871(17) 0.3576(5) 1.1816(8) 0.0166(12) Uani 1 1 d . . . . .
H5 H 0.405922 0.287102 1.175913 0.020 Uiso 1 1 calc R U . . .
C6 C 0.40601(17) 0.1309(5) 0.6498(8) 0.0130(12) Uani 1 1 d . . . . .
C7 C 0.37661(17) 0.1111(5) 0.7946(9) 0.0191(13) Uani 1 1 d . . . . .
H7A H 0.379447 0.033404 0.836195 0.023 Uiso 1 1 calc R U . . .
H7B H 0.384597 0.158882 0.901432 0.023 Uiso 1 1 calc R U . . .
C8 C 0.31223(17) 0.2220(5) 0.7930(8) 0.0166(12) Uani 1 1 d . . . . .
C9 C 0.26834(16) 0.1978(5) 0.7338(8) 0.0145(12) Uani 1 1 d . . . . .
C10 C 0.23408(18) 0.2604(5) 0.7540(8) 0.0185(13) Uani 1 1 d . . . . .
H10 H 0.235725 0.330604 0.812129 0.022 Uiso 1 1 calc R U . . .
C11 C 0.19646(18) 0.2155(6) 0.6843(9) 0.0233(14) Uani 1 1 d . . . . .
H11 H 0.171963 0.255694 0.695550 0.028 Uiso 1 1 calc R U . . .
C12 C 0.19487(18) 0.1137(6) 0.5999(9) 0.0234(14) Uani 1 1 d . . . . .
H12 H 0.169098 0.085390 0.553682 0.028 Uiso 1 1 calc R U . . .
C13 C 0.22979(18) 0.0507(5) 0.5799(8) 0.0181(13) Uani 1 1 d . . . . .
H13 H 0.228409 -0.019454 0.521310 0.022 Uiso 1 1 calc R U . . .
C14 C 0.26670(17) 0.0957(5) 0.6502(8) 0.0126(11) Uani 1 1 d . . . . .
C15 C 0.30922(16) 0.0503(5) 0.6554(8) 0.0136(12) Uani 1 1 d . . . . .
H6OA H 0.452(2) 0.040(2) 1.225(8) 0.03(2) Uiso 1 1 d D . . . .
H6OB H 0.4370(18) 0.122(4) 1.356(5) 0.018(17) 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
Zn1 O6 2.117(4) . ?
Zn1 O6 2.117(4) 2_657 ?
Zn1 O5 2.125(4) . ?
Zn1 O5 2.125(4) 2_657 ?
Zn1 N1 2.157(4) . ?
Zn1 N1 2.157(4) 2_657 ?
O1 C6 1.290(7) . ?
O2 C6 1.227(7) . ?
O3 C8 1.211(7) . ?
O4 C15 1.207(7) . ?
O6 H6OA 0.95(2) . ?
O6 H6OB 0.952(19) . ?
N1 C1 1.341(7) . ?
N1 C5 1.347(7) . ?
N2 C15 1.386(7) . ?
N2 C8 1.391(8) . ?
N2 C7 1.444(7) . ?
C1 C2 1.388(8) . ?
C1 C1 1.492(10) 2_657 ?
C2 C3 1.402(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(8) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.509(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.501(7) . ?
C9 C10 1.375(8) . ?
C9 C14 1.377(8) . ?
C10 C11 1.408(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.499(8) . ?

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
O6 Zn1 O6 105.5(2) . 2_657 ?
O6 Zn1 O5 87.39(15) . . ?
O6 Zn1 O5 86.74(15) 2_657 . ?
O6 Zn1 O5 86.74(15) . 2_657 ?
O6 Zn1 O5 87.39(15) 2_657 2_657 ?
O5 Zn1 O5 170.3(2) . 2_657 ?
O6 Zn1 N1 89.30(16) . . ?
O6 Zn1 N1 164.66(16) 2_657 . ?
O5 Zn1 N1 89.80(15) . . ?
O5 Zn1 N1 97.83(15) 2_657 . ?
O6 Zn1 N1 164.66(16) . 2_657 ?
O6 Zn1 N1 89.30(16) 2_657 2_657 ?
O5 Zn1 N1 97.83(16) . 2_657 ?
O5 Zn1 N1 89.80(16) 2_657 2_657 ?
N1 Zn1 N1 76.4(2) . 2_657 ?
Zn1 O6 H6OA 120(4) . . ?
Zn1 O6 H6OB 108(4) . . ?
H6OA O6 H6OB 103(3) . . ?
C1 N1 C5 118.6(5) . . ?
C1 N1 Zn1 115.8(3) . . ?
C5 N1 Zn1 125.4(4) . . ?
C15 N2 C8 112.5(4) . . ?
C15 N2 C7 121.8(5) . . ?
C8 N2 C7 124.2(5) . . ?
N1 C1 C2 122.0(5) . . ?
N1 C1 C1 116.0(3) . 2_657 ?
C2 C1 C1 122.0(3) . 2_657 ?
C1 C2 C3 118.8(5) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 118.7(6) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 119.3(6) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 122.6(5) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
O2 C6 O1 125.1(5) . . ?
O2 C6 C7 121.8(5) . . ?
O1 C6 C7 113.2(5) . . ?
N2 C7 C6 115.2(5) . . ?
N2 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
N2 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
O3 C8 N2 125.0(5) . . ?
O3 C8 C9 129.3(6) . . ?
N2 C8 C9 105.7(5) . . ?
C10 C9 C14 122.6(5) . . ?
C10 C9 C8 129.6(6) . . ?
C14 C9 C8 107.8(5) . . ?
C9 C10 C11 116.8(6) . . ?
C9 C10 H10 121.6 . . ?
C11 C10 H10 121.6 . . ?
C12 C11 C10 120.5(6) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 122.3(6) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 116.5(6) . . ?
C14 C13 H13 121.7 . . ?
C12 C13 H13 121.7 . . ?
C9 C14 C13 121.2(5) . . ?
C9 C14 C15 108.4(5) . . ?
C13 C14 C15 130.5(5) . . ?
O4 C15 N2 126.0(5) . . ?
O4 C15 C14 128.5(5) . . ?
N2 C15 C14 105.6(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.7(8) . . . . ?
Zn1 N1 C1 C2 176.0(5) . . . . ?
C5 N1 C1 C1 -178.2(6) . . . 2_657 ?
Zn1 N1 C1 C1 -2.9(8) . . . 2_657 ?
N1 C1 C2 C3 -0.8(9) . . . . ?
C1 C1 C2 C3 178.1(7) 2_657 . . . ?
C1 C2 C3 C4 -0.5(10) . . . . ?
C2 C3 C4 C5 1.7(10) . . . . ?
C1 N1 C5 C4 0.6(9) . . . . ?
Zn1 N1 C5 C4 -174.2(5) . . . . ?
C3 C4 C5 N1 -1.9(10) . . . . ?
C15 N2 C7 C6 88.1(7) . . . . ?
C8 N2 C7 C6 -106.9(7) . . . . ?
O2 C6 C7 N2 0.3(9) . . . . ?
O1 C6 C7 N2 -178.9(5) . . . . ?
C15 N2 C8 O3 177.5(6) . . . . ?
C7 N2 C8 O3 11.3(9) . . . . ?
C15 N2 C8 C9 -2.3(6) . . . . ?
C7 N2 C8 C9 -168.5(5) . . . . ?
O3 C8 C9 C10 0.7(11) . . . . ?
N2 C8 C9 C10 -179.5(6) . . . . ?
O3 C8 C9 C14 -179.0(6) . . . . ?
N2 C8 C9 C14 0.8(6) . . . . ?
C14 C9 C10 C11 -0.1(9) . . . . ?
C8 C9 C10 C11 -179.8(6) . . . . ?
C9 C10 C11 C12 -0.2(9) . . . . ?
C10 C11 C12 C13 0.2(10) . . . . ?
C11 C12 C13 C14 0.1(9) . . . . ?
C10 C9 C14 C13 0.4(9) . . . . ?
C8 C9 C14 C13 -179.8(5) . . . . ?
C10 C9 C14 C15 -178.9(5) . . . . ?
C8 C9 C14 C15 0.9(6) . . . . ?
C12 C13 C14 C9 -0.4(9) . . . . ?
C12 C13 C14 C15 178.7(6) . . . . ?
C8 N2 C15 O4 -177.4(6) . . . . ?
C7 N2 C15 O4 -10.9(9) . . . . ?
C8 N2 C15 C14 2.8(6) . . . . ?
C7 N2 C15 C14 169.4(5) . . . . ?
C9 C14 C15 O4 178.1(6) . . . . ?
C13 C14 C15 O4 -1.2(11) . . . . ?
C9 C14 C15 N2 -2.2(6) . . . . ?
C13 C14 C15 N2 178.5(6) . . . . ?

_refine_diff_density_max         2.456
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.156


# start Validation Reply Form
_vrf_PLAT201_shelx               
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) ....... 1 Report
RESPONSE: This is the oxygen atom O5 directly coordinated to the
metal, the structure is severely twinned and there might be 
a disorder of this atom, we have tried several attempts to refine 
this atom splitted in various positions, however, we were unable 
to solve the problem associated with this and considered better to
leave the atom only isotropic as the anisotropic refinement
led to slightly worse factors.
;
_vrf_PLAT430_shelx               
;
PROBLEM: Short Inter D...A Contact O1 ..O5 . 2.64 Ang.
RESPONSE: This is because of the lack of refinement of the H atoms
of O5 due to the disorder/twinned structure.
;
# end Validation Reply Form
####################################################################### 
# 
# 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 1965363'
loop_
_audit_author_name
_audit_author_address
'Santiago Gomez Ruiz'
;University of Rey Juan Carlos 
Spain
;
_audit_update_record             
;
2020-09-18 deposited with the CCDC.	2020-10-26 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         ?
_chemical_formula_sum            'C32 H28 Co N4 O12'
_chemical_formula_weight         719.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Co Co 0.3494 0.9721 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   32.6329(15)
_cell_length_b                   12.9695(4)
_cell_length_c                   7.2447(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.143(2)
_cell_angle_gamma                90
_cell_volume                     3058.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    24938
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      28.69

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             1484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.636
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.686
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.9433.
The λ/2 correction factor is 0.00150.
;
_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 D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41234
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.448
_diffrn_reflns_theta_max         28.728
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3955
_reflns_number_gt                3623
_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 ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0391P)²+2.6025P] 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         3955
_refine_ls_number_parameters     238
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.066
_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
Co1 Co 0.500000 0.20345(2) 0.750000 0.01309(7) Uani 1 2 d S T P . .
O1 O 0.39211(3) 0.15906(8) 0.00531(13) 0.0254(2) Uani 1 1 d . . . . .
O2 O 0.44131(2) 0.10047(7) 0.20915(12) 0.01872(17) Uani 1 1 d . . . . .
O3 O 0.32818(3) 0.28625(8) 0.37249(15) 0.0314(2) Uani 1 1 d . . . . .
O4 O 0.31428(3) -0.03535(8) 0.11950(15) 0.0304(2) Uani 1 1 d . . . . .
O5 O 0.49760(3) 0.17267(7) 0.47571(12) 0.01944(17) Uani 1 1 d D . . . .
H5OA H 0.4750(5) 0.1465(15) 0.414(3) 0.045(6) Uiso 1 1 d D . . . .
H5OB H 0.5202(5) 0.1451(16) 0.418(3) 0.051(6) Uiso 1 1 d D . . . .
O6 O 0.44469(3) 0.11105(7) 0.73944(13) 0.01920(18) Uani 1 1 d D . . . .
H6OA H 0.4473(7) 0.0414(12) 0.735(3) 0.054(6) Uiso 1 1 d D . . . .
H6OB H 0.4278(6) 0.1255(15) 0.831(3) 0.047(6) Uiso 1 1 d D . . . .
N1 N 0.45864(3) 0.33328(8) 0.71198(14) 0.01570(19) Uani 1 1 d . . . . .
N2 N 0.33152(3) 0.12276(8) 0.24941(14) 0.0180(2) Uani 1 1 d . . . . .
C1 C 0.47802(3) 0.42597(8) 0.72770(14) 0.0131(2) Uani 1 1 d . . . . .
C2 C 0.45719(4) 0.52055(9) 0.70384(16) 0.0158(2) Uani 1 1 d . . . . .
C3 C 0.41448(4) 0.51720(10) 0.65625(17) 0.0201(2) Uani 1 1 d . . . . .
H3 H 0.399218 0.579295 0.639639 0.024 Uiso 1 1 calc R U . . .
C4 C 0.39523(4) 0.42365(10) 0.63422(18) 0.0218(2) Uani 1 1 d . . . . .
H4 H 0.366682 0.420047 0.598414 0.026 Uiso 1 1 calc R U . . .
C5 C 0.41836(4) 0.33319(9) 0.66539(18) 0.0201(2) Uani 1 1 d . . . . .
H5 H 0.404614 0.268730 0.652660 0.024 Uiso 1 1 calc R U . . .
C6 C 0.47947(4) 0.61509(9) 0.72754(18) 0.0210(2) Uani 1 1 d . . . . .
H6 H 0.465309 0.678818 0.711575 0.025 Uiso 1 1 calc R U . . .
C7 C 0.40405(3) 0.12349(8) 0.15782(16) 0.0152(2) Uani 1 1 d . . . . .
C8 C 0.37400(4) 0.10004(11) 0.30385(18) 0.0226(3) Uani 1 1 d . . . . .
H8A H 0.376290 0.026032 0.336427 0.027 Uiso 1 1 calc R U . . .
H8B H 0.382272 0.140144 0.416708 0.027 Uiso 1 1 calc R U . . .
C9 C 0.31153(4) 0.21277(10) 0.29723(17) 0.0192(2) Uani 1 1 d . . . . .
C10 C 0.26725(4) 0.19649(10) 0.23669(16) 0.0186(2) Uani 1 1 d . . . . .
C11 C 0.23389(4) 0.26086(12) 0.24823(19) 0.0267(3) Uani 1 1 d . . . . .
H11 H 0.236726 0.327239 0.303119 0.032 Uiso 1 1 calc R U . . .
C12 C 0.19578(4) 0.22450(14) 0.1760(2) 0.0343(3) Uani 1 1 d . . . . .
H12 H 0.172192 0.267097 0.180601 0.041 Uiso 1 1 calc R U . . .
C13 C 0.19183(4) 0.12736(15) 0.0977(2) 0.0352(4) Uani 1 1 d . . . . .
H13 H 0.165525 0.104739 0.049325 0.042 Uiso 1 1 calc R U . . .
C14 C 0.22553(4) 0.06175(12) 0.08795(19) 0.0283(3) Uani 1 1 d . . . . .
H14 H 0.222749 -0.005160 0.035145 0.034 Uiso 1 1 calc R U . . .
C15 C 0.26319(3) 0.09895(10) 0.15901(17) 0.0190(2) Uani 1 1 d . . . . .
C16 C 0.30454(4) 0.04990(10) 0.16864(17) 0.0191(2) 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
Co1 O5 2.0228(9) 2_656 ?
Co1 O5 2.0228(9) . ?
Co1 N1 2.1631(10) . ?
Co1 N1 2.1632(10) 2_656 ?
Co1 O6 2.1634(8) . ?
Co1 O6 2.1634(8) 2_656 ?
O1 C7 1.2342(15) . ?
O2 C7 1.2809(13) . ?
O3 C9 1.2073(16) . ?
O4 C16 1.2111(16) . ?
O5 H5OA 0.900(14) . ?
O5 H5OB 0.941(14) . ?
O6 H6OA 0.908(15) . ?
O6 H6OB 0.912(14) . ?
N1 C5 1.3335(15) . ?
N1 C1 1.3592(14) . ?
N2 C16 1.3914(15) . ?
N2 C9 1.3932(15) . ?
N2 C8 1.4440(14) . ?
C1 C2 1.4070(15) . ?
C1 C1 1.448(2) 2_656 ?
C2 C3 1.4121(16) . ?
C2 C6 1.4294(16) . ?
C3 C4 1.3703(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.4044(17) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C6 1.356(2) 2_656 ?
C6 H6 0.9500 . ?
C7 C8 1.5243(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.4943(16) . ?
C10 C11 1.3793(17) . ?
C10 C15 1.3871(18) . ?
C11 C12 1.396(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3844(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.4890(16) . ?

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
O5 Co1 O5 157.24(6) 2_656 . ?
O5 Co1 N1 104.96(4) 2_656 . ?
O5 Co1 N1 92.81(4) . . ?
O5 Co1 N1 92.81(4) 2_656 2_656 ?
O5 Co1 N1 104.96(4) . 2_656 ?
N1 Co1 N1 77.76(5) . 2_656 ?
O5 Co1 O6 84.17(3) 2_656 . ?
O5 Co1 O6 83.28(3) . . ?
N1 Co1 O6 85.15(4) . . ?
N1 Co1 O6 161.27(4) 2_656 . ?
O5 Co1 O6 83.28(3) 2_656 2_656 ?
O5 Co1 O6 84.17(3) . 2_656 ?
N1 Co1 O6 161.27(4) . 2_656 ?
N1 Co1 O6 85.15(4) 2_656 2_656 ?
O6 Co1 O6 112.72(5) . 2_656 ?
Co1 O5 H5OA 122.2(13) . . ?
Co1 O5 H5OB 122.1(13) . . ?
H5OA O5 H5OB 106.1(15) . . ?
Co1 O6 H6OA 118.2(14) . . ?
Co1 O6 H6OB 113.9(13) . . ?
H6OA O6 H6OB 106.9(16) . . ?
C5 N1 C1 117.79(10) . . ?
C5 N1 Co1 128.77(8) . . ?
C1 N1 Co1 113.30(7) . . ?
C16 N2 C9 112.35(10) . . ?
C16 N2 C8 122.82(11) . . ?
C9 N2 C8 124.10(11) . . ?
N1 C1 C2 122.90(10) . . ?
N1 C1 C1 117.79(6) . 2_656 ?
C2 C1 C1 119.31(6) . 2_656 ?
C1 C2 C3 117.56(10) . . ?
C1 C2 C6 119.74(10) . . ?
C3 C2 C6 122.70(11) . . ?
C4 C3 C2 119.46(11) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 118.98(11) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 123.26(11) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C6 C6 C2 120.94(7) 2_656 . ?
C6 C6 H6 119.5 2_656 . ?
C2 C6 H6 119.5 . . ?
O1 C7 O2 125.37(11) . . ?
O1 C7 C8 121.23(10) . . ?
O2 C7 C8 113.38(10) . . ?
N2 C8 C7 115.01(10) . . ?
N2 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
N2 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
O3 C9 N2 124.76(12) . . ?
O3 C9 C10 129.65(12) . . ?
N2 C9 C10 105.59(10) . . ?
C11 C10 C15 121.59(12) . . ?
C11 C10 C9 130.35(12) . . ?
C15 C10 C9 108.07(10) . . ?
C10 C11 C12 117.29(14) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C13 C12 C11 121.01(13) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 121.70(13) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 116.73(14) . . ?
C15 C14 H14 121.6 . . ?
C13 C14 H14 121.6 . . ?
C14 C15 C10 121.68(12) . . ?
C14 C15 C16 130.21(12) . . ?
C10 C15 C16 108.11(10) . . ?
O4 C16 N2 124.90(12) . . ?
O4 C16 C15 129.23(12) . . ?
N2 C16 C15 105.86(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 2.43(17) . . . . ?
Co1 N1 C1 C2 178.49(8) . . . . ?
C5 N1 C1 C1 -178.01(12) . . . 2_656 ?
Co1 N1 C1 C1 -1.95(15) . . . 2_656 ?
N1 C1 C2 C3 -1.88(17) . . . . ?
C1 C1 C2 C3 178.57(12) 2_656 . . . ?
N1 C1 C2 C6 178.28(11) . . . . ?
C1 C1 C2 C6 -1.26(19) 2_656 . . . ?
C1 C2 C3 C4 -0.41(18) . . . . ?
C6 C2 C3 C4 179.42(12) . . . . ?
C2 C3 C4 C5 1.99(19) . . . . ?
C1 N1 C5 C4 -0.73(18) . . . . ?
Co1 N1 C5 C4 -176.09(9) . . . . ?
C3 C4 C5 N1 -1.5(2) . . . . ?
C1 C2 C6 C6 0.1(2) . . . 2_656 ?
C3 C2 C6 C6 -179.70(15) . . . 2_656 ?
C16 N2 C8 C7 92.54(14) . . . . ?
C9 N2 C8 C7 -98.02(14) . . . . ?
O1 C7 C8 N2 -0.14(18) . . . . ?
O2 C7 C8 N2 -178.64(11) . . . . ?
C16 N2 C9 O3 178.43(13) . . . . ?
C8 N2 C9 O3 8.0(2) . . . . ?
C16 N2 C9 C10 -1.38(13) . . . . ?
C8 N2 C9 C10 -171.80(10) . . . . ?
O3 C9 C10 C11 0.9(2) . . . . ?
N2 C9 C10 C11 -179.28(13) . . . . ?
O3 C9 C10 C15 -179.22(14) . . . . ?
N2 C9 C10 C15 0.58(13) . . . . ?
C15 C10 C11 C12 -0.91(19) . . . . ?
C9 C10 C11 C12 178.94(13) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 C10 0.22(19) . . . . ?
C13 C14 C15 C16 -179.42(13) . . . . ?
C11 C10 C15 C14 0.53(19) . . . . ?
C9 C10 C15 C14 -179.35(12) . . . . ?
C11 C10 C15 C16 -179.77(11) . . . . ?
C9 C10 C15 C16 0.35(13) . . . . ?
C9 N2 C16 O4 -178.04(12) . . . . ?
C8 N2 C16 O4 -7.48(19) . . . . ?
C9 N2 C16 C15 1.59(13) . . . . ?
C8 N2 C16 C15 172.15(10) . . . . ?
C14 C15 C16 O4 -1.9(2) . . . . ?
C10 C15 C16 O4 178.45(13) . . . . ?
C14 C15 C16 N2 178.51(13) . . . . ?
C10 C15 C16 N2 -1.16(13) . . . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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 1965362'
loop_
_audit_author_name
_audit_author_address
'Santiago Gomez Ruiz'
;University of Rey Juan Carlos 
Spain
;
_audit_update_record             
;
2020-09-18 deposited with the CCDC.	2020-10-26 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         ?
_chemical_formula_sum            'C30 H28 Co N4 O12'
_chemical_formula_weight         695.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Co Co 0.3494 0.9721 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   32.8560(15)
_cell_length_b                   12.1150(6)
_cell_length_c                   7.2898(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.678(2)
_cell_angle_gamma                90
_cell_volume                     2892.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12332
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      28.83

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             1436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.670
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.9433.
The λ/2 correction factor is 0.00150.
;
_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 D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23999
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.488
_diffrn_reflns_theta_max         28.818
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3737
_reflns_number_gt                3303
_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 ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0274P)²+3.4566P] 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         3737
_refine_ls_number_parameters     229
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.062
_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
Co1 Co 0.000000 0.22350(2) 0.250000 0.01021(7) Uani 1 2 d S T P . .
O1 O 0.89425(3) 0.83845(9) -0.00809(13) 0.0202(2) Uani 1 1 d . . . . .
O2 O 0.94380(3) 0.88641(8) 0.20526(13) 0.01587(19) Uani 1 1 d . . . . .
O3 O 0.82059(3) 1.03870(9) 0.10188(15) 0.0240(2) Uani 1 1 d . . . . .
O4 O 0.82708(3) 0.69817(9) 0.37289(15) 0.0255(2) Uani 1 1 d . . . . .
O5 O -0.00262(3) 0.20907(8) -0.03236(13) 0.01544(19) Uani 1 1 d D . . . .
H5OA H -0.0248(5) 0.1789(17) -0.090(3) 0.041(6) Uiso 1 1 d D . . . .
H5OB H 0.0196(5) 0.1765(18) -0.084(3) 0.051(7) Uiso 1 1 d D . . . .
O6 O -0.05068(3) 0.11441(8) 0.24127(13) 0.0177(2) Uani 1 1 d D . . . .
H6OA H -0.0692(6) 0.1286(16) 0.328(3) 0.045(6) Uiso 1 1 d D . . . .
H6OB H -0.0481(7) 0.0393(13) 0.233(3) 0.045(6) Uiso 1 1 d D . . . .
N1 N 0.04079(3) 0.36110(9) 0.27748(14) 0.0134(2) Uani 1 1 d . . . . .
N2 N 0.83430(3) 0.86882(10) 0.23719(15) 0.0154(2) Uani 1 1 d . . . . .
C1 C 0.02265(4) 0.46116(10) 0.26965(17) 0.0135(2) Uani 1 1 d . . . . .
C2 C 0.04504(4) 0.55827(11) 0.2980(2) 0.0208(3) Uani 1 1 d . . . . .
H2 H 0.031739 0.627938 0.290851 0.025 Uiso 1 1 calc R U . . .
C3 C 0.08701(5) 0.55180(12) 0.3368(2) 0.0234(3) Uani 1 1 d . . . . .
H3 H 0.102846 0.617016 0.355969 0.028 Uiso 1 1 calc R U . . .
C4 C 0.10555(4) 0.44903(12) 0.3472(2) 0.0201(3) Uani 1 1 d . . . . .
H4 H 0.134195 0.442341 0.375064 0.024 Uiso 1 1 calc R U . . .
C5 C 0.08131(4) 0.35623(11) 0.31613(19) 0.0173(3) Uani 1 1 d . . . . .
H5 H 0.094043 0.285781 0.322528 0.021 Uiso 1 1 calc R U . . .
C6 C 0.90646(4) 0.86804(10) 0.14913(17) 0.0124(2) Uani 1 1 d . . . . .
C7 C 0.87679(4) 0.88797(13) 0.29523(18) 0.0189(3) Uani 1 1 d . . . . .
H7A H 0.884570 0.839541 0.401748 0.023 Uiso 1 1 calc R U . . .
H7B H 0.879879 0.965293 0.338048 0.023 Uiso 1 1 calc R U . . .
C8 C 0.80901(4) 0.94995(11) 0.15413(17) 0.0157(3) Uani 1 1 d . . . . .
C9 C 0.76676(4) 0.90516(11) 0.14906(17) 0.0144(2) Uani 1 1 d . . . . .
C10 C 0.73001(4) 0.94988(12) 0.07851(19) 0.0194(3) Uani 1 1 d . . . . .
H10 H 0.728743 1.019942 0.019803 0.023 Uiso 1 1 calc R U . . .
C11 C 0.69492(4) 0.88752(13) 0.0974(2) 0.0230(3) Uani 1 1 d . . . . .
H11 H 0.669179 0.915853 0.050553 0.028 Uiso 1 1 calc R U . . .
C12 C 0.69666(4) 0.78480(13) 0.1833(2) 0.0227(3) Uani 1 1 d . . . . .
H12 H 0.672197 0.744407 0.194208 0.027 Uiso 1 1 calc R U . . .
C13 C 0.73396(4) 0.74045(12) 0.2534(2) 0.0198(3) Uani 1 1 d . . . . .
H13 H 0.735397 0.670450 0.312331 0.024 Uiso 1 1 calc R U . . .
C14 C 0.76863(4) 0.80217(11) 0.23402(18) 0.0151(3) Uani 1 1 d . . . . .
C15 C 0.81230(4) 0.77792(11) 0.29309(18) 0.0161(3) 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
Co1 O5 2.0606(9) 2 ?
Co1 O5 2.0606(9) . ?
Co1 O6 2.1226(10) 2 ?
Co1 O6 2.1227(10) . ?
Co1 N1 2.1380(11) . ?
Co1 N1 2.1380(11) 2 ?
O1 C6 1.2362(16) . ?
O2 C6 1.2807(16) . ?
O3 C8 1.2123(17) . ?
O4 C15 1.2089(17) . ?
O5 H5OA 0.892(14) . ?
O5 H5OB 0.936(15) . ?
O6 H6OA 0.926(15) . ?
O6 H6OB 0.916(15) . ?
N1 C5 1.3396(17) . ?
N1 C1 1.3499(16) . ?
N2 C8 1.3932(17) . ?
N2 C15 1.3963(17) . ?
N2 C7 1.4442(17) . ?
C1 C2 1.3941(18) . ?
C1 C1 1.493(3) 2 ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3857(19) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.5206(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.4883(18) . ?
C9 C10 1.3837(19) . ?
C9 C14 1.3920(18) . ?
C10 C11 1.395(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3797(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.4931(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Co1 O5 170.27(6) 2 . ?
O5 Co1 O6 87.04(4) 2 2 ?
O5 Co1 O6 86.90(4) . 2 ?
O5 Co1 O6 86.90(4) 2 . ?
O5 Co1 O6 87.04(4) . . ?
O6 Co1 O6 102.98(6) 2 . ?
O5 Co1 N1 89.87(4) 2 . ?
O5 Co1 N1 97.73(4) . . ?
O6 Co1 N1 89.92(4) 2 . ?
O6 Co1 N1 166.50(4) . . ?
O5 Co1 N1 97.74(4) 2 2 ?
O5 Co1 N1 89.87(4) . 2 ?
O6 Co1 N1 166.51(4) 2 2 ?
O6 Co1 N1 89.91(4) . 2 ?
N1 Co1 N1 77.53(6) . 2 ?
Co1 O5 H5OA 118.3(13) . . ?
Co1 O5 H5OB 117.7(14) . . ?
H5OA O5 H5OB 105.9(16) . . ?
Co1 O6 H6OA 114.9(13) . . ?
Co1 O6 H6OB 123.0(14) . . ?
H6OA O6 H6OB 107.5(16) . . ?
C5 N1 C1 118.43(11) . . ?
C5 N1 Co1 126.16(9) . . ?
C1 N1 Co1 115.16(9) . . ?
C8 N2 C15 112.25(11) . . ?
C8 N2 C7 122.82(12) . . ?
C15 N2 C7 123.53(12) . . ?
N1 C1 C2 121.72(12) . . ?
N1 C1 C1 115.97(7) . 2 ?
C2 C1 C1 122.31(8) . 2 ?
C3 C2 C1 119.11(13) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 119.16(13) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 118.42(13) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 123.15(13) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
O1 C6 O2 125.22(12) . . ?
O1 C6 C7 121.15(12) . . ?
O2 C6 C7 113.62(11) . . ?
N2 C7 C6 115.40(11) . . ?
N2 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
N2 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
O3 C8 N2 124.82(13) . . ?
O3 C8 C9 129.17(13) . . ?
N2 C8 C9 105.99(11) . . ?
C10 C9 C14 121.46(13) . . ?
C10 C9 C8 130.57(12) . . ?
C14 C9 C8 107.97(11) . . ?
C9 C10 C11 117.04(13) . . ?
C9 C10 H10 121.5 . . ?
C11 C10 H10 121.5 . . ?
C12 C11 C10 121.64(13) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 120.77(13) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 117.46(13) . . ?
C14 C13 H13 121.3 . . ?
C12 C13 H13 121.3 . . ?
C13 C14 C9 121.64(13) . . ?
C13 C14 C15 130.23(13) . . ?
C9 C14 C15 108.14(12) . . ?
O4 C15 N2 125.00(13) . . ?
O4 C15 C14 129.41(13) . . ?
N2 C15 C14 105.59(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.92(19) . . . . ?
Co1 N1 C1 C2 175.53(10) . . . . ?
C5 N1 C1 C1 -178.63(13) . . . 2 ?
Co1 N1 C1 C1 -4.02(17) . . . 2 ?
N1 C1 C2 C3 -0.5(2) . . . . ?
C1 C1 C2 C3 178.98(15) 2 . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C1 N1 C5 C4 -0.5(2) . . . . ?
Co1 N1 C5 C4 -174.41(10) . . . . ?
C3 C4 C5 N1 -0.4(2) . . . . ?
C8 N2 C7 C6 -87.65(16) . . . . ?
C15 N2 C7 C6 106.91(14) . . . . ?
O1 C6 C7 N2 0.62(19) . . . . ?
O2 C6 C7 N2 179.65(11) . . . . ?
C15 N2 C8 O3 176.36(13) . . . . ?
C7 N2 C8 O3 9.4(2) . . . . ?
C15 N2 C8 C9 -2.48(14) . . . . ?
C7 N2 C8 C9 -169.40(11) . . . . ?
O3 C8 C9 C10 2.7(2) . . . . ?
N2 C8 C9 C10 -178.52(13) . . . . ?
O3 C8 C9 C14 -176.79(14) . . . . ?
N2 C8 C9 C14 1.98(14) . . . . ?
C14 C9 C10 C11 0.4(2) . . . . ?
C8 C9 C10 C11 -179.02(13) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 C9 0.5(2) . . . . ?
C12 C13 C14 C15 -179.89(13) . . . . ?
C10 C9 C14 C13 -0.6(2) . . . . ?
C8 C9 C14 C13 178.91(12) . . . . ?
C10 C9 C14 C15 179.63(12) . . . . ?
C8 C9 C14 C15 -0.82(14) . . . . ?
C8 N2 C15 O4 -177.87(13) . . . . ?
C7 N2 C15 O4 -11.1(2) . . . . ?
C8 N2 C15 C14 1.99(14) . . . . ?
C7 N2 C15 C14 168.79(11) . . . . ?
C13 C14 C15 O4 -0.5(2) . . . . ?
C9 C14 C15 O4 179.21(14) . . . . ?
C13 C14 C15 N2 179.67(13) . . . . ?
C9 C14 C15 N2 -0.64(14) . . . . ?

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.059

