# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_5-3
_database_code_depnum_ccdc_archive 'CCDC 1445806'
_audit_update_record             
;
2016-10-19 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 Cu N5 O8'
_chemical_formula_sum            'C18 H15 Cu N5 O8'
_chemical_formula_weight         492.89

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

loop_
_symmetry_equiv_pos_as_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                   10.0651(14)
_cell_length_b                   12.3010(17)
_cell_length_c                   16.281(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.537(2)
_cell_angle_gamma                90.00
_cell_volume                     2012.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6871
_cell_measurement_theta_min      25.89
_cell_measurement_theta_max      2.32

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1004
_exptl_absorpt_coefficient_mu    1.144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6513
_exptl_absorpt_correction_T_max  0.8749
_exptl_absorpt_process_details   'SADABS (Bruker, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19824
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4114
_reflns_number_gt                3366
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0504P)²+0.6551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4114
_refine_ls_number_parameters     299
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.215
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.17703(3) 0.58581(2) 0.15618(2) 0.04358(13) Uani 1 1 d . . .
O1 O 0.01947(17) 0.50178(13) 0.18737(13) 0.0491(5) Uani 1 1 d . . .
O5 O 0.0600(2) 0.71256(14) 0.13150(16) 0.0595(5) Uani 1 1 d . . .
N2 N 0.2534(2) 0.44060(17) 0.15753(13) 0.0438(5) Uani 1 1 d . . .
N1 N 0.3431(2) 0.65209(19) 0.11583(14) 0.0491(5) Uani 1 1 d . . .
C7 C 0.0403(3) 0.40149(19) 0.19032(16) 0.0429(6) Uani 1 1 d . . .
C9 C 0.3728(3) 0.4110(2) 0.14633(18) 0.0532(7) Uani 1 1 d . . .
H9 H 0.3952 0.3384 0.1552 0.064 Uiso 1 1 calc R . .
N5 N 0.0122(2) 0.70251(19) 0.05622(19) 0.0586(7) Uani 1 1 d . . .
C5 C -0.0739(3) 0.2236(2) 0.16651(19) 0.0568(7) Uani 1 1 d . . .
H5 H -0.0077 0.2023 0.1325 0.068 Uiso 1 1 calc R . .
O6 O -0.0652(2) 0.77183(19) 0.02805(19) 0.0900(8) Uani 1 1 d . . .
N3 N 0.1613(2) 0.36345(16) 0.17764(14) 0.0477(5) Uani 1 1 d . . .
H3 H 0.1807 0.2955 0.1817 0.057 Uiso 1 1 calc R . .
O7 O 0.0453(2) 0.62355(19) 0.01664(16) 0.0747(6) Uani 1 1 d . . .
C18 C 0.4595(3) 0.5973(3) 0.10418(16) 0.0518(7) Uani 1 1 d . . .
N4 N 0.2175(3) 0.5982(2) 0.34385(17) 0.0658(7) Uani 1 1 d U . .
C6 C -0.0669(3) 0.32412(19) 0.20629(16) 0.0447(6) Uani 1 1 d . . .
O2 O 0.2275(3) 0.65769(17) 0.28158(14) 0.0752(7) Uani 1 1 d U A .
C2 C -0.2685(3) 0.2859(2) 0.27021(18) 0.0581(7) Uani 1 1 d . . .
H2 H -0.3335 0.3062 0.3054 0.070 Uiso 1 1 calc R . .
C1 C -0.1650(3) 0.3559(2) 0.25736(17) 0.0496(6) Uani 1 1 d . . .
H1 H -0.1610 0.4237 0.2827 0.060 Uiso 1 1 calc R . .
O8 O -0.2015(3) 0.05885(19) 0.13993(19) 0.1012(10) Uani 1 1 d U . .
C10 C 0.4747(3) 0.4839(3) 0.12067(17) 0.0546(7) Uani 1 1 d . . .
C4 C -0.1813(4) 0.1559(2) 0.1787(2) 0.0664(9) Uani 1 1 d . . .
C13 C 0.6891(3) 0.5987(4) 0.0611(2) 0.0821(11) Uani 1 1 d U . .
H13 H 0.7602 0.6364 0.0408 0.099 Uiso 1 1 calc R . .
C14 C 0.5692(3) 0.6552(3) 0.07330(19) 0.0656(9) Uani 1 1 d U . .
C3 C -0.2772(3) 0.1865(2) 0.2317(2) 0.0650(8) Uani 1 1 d . . .
H3A H -0.3473 0.1398 0.2413 0.078 Uiso 1 1 calc R . .
O4 O 0.2257(4) 0.5013(2) 0.3392(2) 0.1177(12) Uani 1 1 d U A .
C11 C 0.5961(3) 0.4345(3) 0.1076(2) 0.0706(9) Uani 1 1 d U . .
H11 H 0.6070 0.3608 0.1189 0.085 Uiso 1 1 calc R . .
C15 C 0.5555(4) 0.7650(4) 0.0550(2) 0.0810(11) Uani 1 1 d U . .
H15 H 0.6262 0.8029 0.0344 0.097 Uiso 1 1 calc R . .
C16 C 0.4399(4) 0.8173(3) 0.0671(2) 0.0812(11) Uani 1 1 d . . .
H16 H 0.4294 0.8907 0.0545 0.097 Uiso 1 1 calc R . .
C17 C 0.3369(3) 0.7575(3) 0.0990(2) 0.0648(8) Uani 1 1 d . . .
H17 H 0.2587 0.7941 0.1092 0.078 Uiso 1 1 calc R . .
O3 O 0.2394(8) 0.6460(7) 0.4077(4) 0.090(2) Uani 0.50 1 d PU A 1
C8 C -0.1108(6) 0.0263(3) 0.0817(4) 0.124(2) Uani 1 1 d U . .
H8A H -0.0992 0.0844 0.0434 0.186 Uiso 1 1 calc R . .
H8B H -0.1450 -0.0366 0.0525 0.186 Uiso 1 1 calc R . .
H8C H -0.0267 0.0089 0.1095 0.186 Uiso 1 1 calc R . .
C12 C 0.7025(3) 0.4938(4) 0.0778(2) 0.0841(12) Uani 1 1 d U . .
H12 H 0.7827 0.4591 0.0697 0.101 Uiso 1 1 calc R . .
O3' O 0.1567(10) 0.6372(9) 0.4025(6) 0.121(3) Uani 0.50 1 d PU A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.944(2) . ?
Cu1 O5 1.980(2) . ?
Cu1 O1 1.9851(17) . ?
Cu1 N1 2.006(2) . ?
Cu1 O2 2.254(2) . ?
O1 C7 1.252(3) . ?
O5 N5 1.295(3) . ?
N2 C9 1.280(3) . ?
N2 N3 1.380(3) . ?
N1 C17 1.326(4) . ?
N1 C18 1.376(3) . ?
C7 N3 1.333(3) . ?
C7 C6 1.474(3) . ?
C9 C10 1.444(4) . ?
C9 H9 0.9300 . ?
N5 O7 1.223(3) . ?
N5 O6 1.225(3) . ?
C5 C4 1.389(4) . ?
C5 C6 1.395(4) . ?
C5 H5 0.9300 . ?
N3 H3 0.8600 . ?
C18 C10 1.426(4) . ?
C18 C14 1.430(4) . ?
N4 O4 1.198(3) . ?
N4 O3 1.203(7) . ?
N4 O2 1.260(3) . ?
N4 O3' 1.261(8) . ?
C6 C1 1.386(4) . ?
C2 C3 1.375(4) . ?
C2 C1 1.377(4) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
O8 C4 1.360(4) . ?
O8 C8 1.414(5) . ?
C10 C11 1.392(4) . ?
C4 C3 1.386(4) . ?
C13 C12 1.324(6) . ?
C13 C14 1.417(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(6) . ?
C3 H3A 0.9300 . ?
C11 C12 1.408(5) . ?
C11 H11 0.9300 . ?
C15 C16 1.355(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.398(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 O5 162.84(10) . . ?
N2 Cu1 O1 80.80(8) . . ?
O5 Cu1 O1 89.28(7) . . ?
N2 Cu1 N1 92.32(9) . . ?
O5 Cu1 N1 96.36(9) . . ?
O1 Cu1 N1 171.96(8) . . ?
N2 Cu1 O2 106.45(9) . . ?
O5 Cu1 O2 88.45(10) . . ?
O1 Cu1 O2 96.41(8) . . ?
N1 Cu1 O2 89.50(9) . . ?
C7 O1 Cu1 112.87(16) . . ?
N5 O5 Cu1 107.38(15) . . ?
C9 N2 N3 119.2(2) . . ?
C9 N2 Cu1 129.3(2) . . ?
N3 N2 Cu1 111.34(14) . . ?
C17 N1 C18 118.7(3) . . ?
C17 N1 Cu1 115.8(2) . . ?
C18 N1 Cu1 125.48(19) . . ?
O1 C7 N3 119.5(2) . . ?
O1 C7 C6 121.4(2) . . ?
N3 C7 C6 119.1(2) . . ?
N2 C9 C10 123.7(3) . . ?
N2 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
O7 N5 O6 122.9(3) . . ?
O7 N5 O5 118.5(2) . . ?
O6 N5 O5 118.6(3) . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 N3 N2 115.4(2) . . ?
C7 N3 H3 122.3 . . ?
N2 N3 H3 122.3 . . ?
N1 C18 C10 122.4(2) . . ?
N1 C18 C14 119.1(3) . . ?
C10 C18 C14 118.5(3) . . ?
O4 N4 O3 122.1(5) . . ?
O4 N4 O2 121.2(3) . . ?
O3 N4 O2 113.1(5) . . ?
O4 N4 O3' 117.7(6) . . ?
O3 N4 O3' 39.7(4) . . ?
O2 N4 O3' 117.1(6) . . ?
C1 C6 C5 120.7(2) . . ?
C1 C6 C7 118.7(2) . . ?
C5 C6 C7 120.4(2) . . ?
N4 O2 Cu1 118.44(17) . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C1 C6 119.3(2) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C4 O8 C8 118.4(3) . . ?
C11 C10 C18 118.9(3) . . ?
C11 C10 C9 114.7(3) . . ?
C18 C10 C9 126.3(2) . . ?
O8 C4 C3 115.9(3) . . ?
O8 C4 C5 123.8(3) . . ?
C3 C4 C5 120.3(3) . . ?
C12 C13 C14 121.7(3) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 C18 119.4(3) . . ?
C13 C14 C18 119.2(4) . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C10 C11 C12 121.3(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 117.9(4) . . ?
C15 C16 H16 121.1 . . ?
C17 C16 H16 121.1 . . ?
N1 C17 C16 124.4(3) . . ?
N1 C17 H17 117.8 . . ?
C16 C17 H17 117.8 . . ?
O8 C8 H8A 109.5 . . ?
O8 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O8 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?

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
N2 Cu1 O1 C7 -2.15(19) . . . . ?
O5 Cu1 O1 C7 163.8(2) . . . . ?
N1 Cu1 O1 C7 29.2(7) . . . . ?
O2 Cu1 O1 C7 -107.8(2) . . . . ?
N2 Cu1 O5 N5 -32.1(4) . . . . ?
O1 Cu1 O5 N5 -86.40(15) . . . . ?
N1 Cu1 O5 N5 87.85(16) . . . . ?
O2 Cu1 O5 N5 177.18(15) . . . . ?
O5 Cu1 N2 C9 128.3(3) . . . . ?
O1 Cu1 N2 C9 -176.3(3) . . . . ?
N1 Cu1 N2 C9 7.9(3) . . . . ?
O2 Cu1 N2 C9 -82.2(3) . . . . ?
O5 Cu1 N2 N3 -55.0(4) . . . . ?
O1 Cu1 N2 N3 0.42(17) . . . . ?
N1 Cu1 N2 N3 -175.40(17) . . . . ?
O2 Cu1 N2 N3 94.43(17) . . . . ?
N2 Cu1 N1 C17 175.6(2) . . . . ?
O5 Cu1 N1 C17 10.4(2) . . . . ?
O1 Cu1 N1 C17 144.6(6) . . . . ?
O2 Cu1 N1 C17 -77.9(2) . . . . ?
N2 Cu1 N1 C18 -4.0(2) . . . . ?
O5 Cu1 N1 C18 -169.2(2) . . . . ?
O1 Cu1 N1 C18 -35.0(8) . . . . ?
O2 Cu1 N1 C18 102.5(2) . . . . ?
Cu1 O1 C7 N3 3.6(3) . . . . ?
Cu1 O1 C7 C6 -175.4(2) . . . . ?
N3 N2 C9 C10 176.4(2) . . . . ?
Cu1 N2 C9 C10 -7.1(4) . . . . ?
Cu1 O5 N5 O7 -0.4(3) . . . . ?
Cu1 O5 N5 O6 178.91(19) . . . . ?
O1 C7 N3 N2 -3.4(4) . . . . ?
C6 C7 N3 N2 175.7(2) . . . . ?
C9 N2 N3 C7 178.3(2) . . . . ?
Cu1 N2 N3 C7 1.3(3) . . . . ?
C17 N1 C18 C10 -180.0(3) . . . . ?
Cu1 N1 C18 C10 -0.4(4) . . . . ?
C17 N1 C18 C14 -0.9(4) . . . . ?
Cu1 N1 C18 C14 178.67(19) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?
C4 C5 C6 C7 -175.6(3) . . . . ?
O1 C7 C6 C1 -32.9(4) . . . . ?
N3 C7 C6 C1 148.0(3) . . . . ?
O1 C7 C6 C5 143.0(3) . . . . ?
N3 C7 C6 C5 -36.0(4) . . . . ?
O4 N4 O2 Cu1 24.9(5) . . . . ?
O3 N4 O2 Cu1 -176.0(5) . . . . ?
O3' N4 O2 Cu1 -132.2(6) . . . . ?
N2 Cu1 O2 N4 -42.0(3) . . . . ?
O5 Cu1 O2 N4 129.4(3) . . . . ?
O1 Cu1 O2 N4 40.3(3) . . . . ?
N1 Cu1 O2 N4 -134.3(3) . . . . ?
C3 C2 C1 C6 -1.5(5) . . . . ?
C5 C6 C1 C2 1.6(4) . . . . ?
C7 C6 C1 C2 177.5(3) . . . . ?
N1 C18 C10 C11 -179.7(3) . . . . ?
C14 C18 C10 C11 1.2(4) . . . . ?
N1 C18 C10 C9 3.7(4) . . . . ?
C14 C18 C10 C9 -175.3(3) . . . . ?
N2 C9 C10 C11 -176.6(3) . . . . ?
N2 C9 C10 C18 0.0(5) . . . . ?
C8 O8 C4 C3 176.6(4) . . . . ?
C8 O8 C4 C5 -2.3(6) . . . . ?
C6 C5 C4 O8 176.6(3) . . . . ?
C6 C5 C4 C3 -2.2(5) . . . . ?
C12 C13 C14 C15 -179.5(3) . . . . ?
C12 C13 C14 C18 -0.2(5) . . . . ?
N1 C18 C14 C15 -0.6(4) . . . . ?
C10 C18 C14 C15 178.5(3) . . . . ?
N1 C18 C14 C13 -179.8(3) . . . . ?
C10 C18 C14 C13 -0.7(4) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
O8 C4 C3 C2 -176.6(3) . . . . ?
C5 C4 C3 C2 2.3(5) . . . . ?
C18 C10 C11 C12 -0.8(4) . . . . ?
C9 C10 C11 C12 176.2(3) . . . . ?
C13 C14 C15 C16 179.9(3) . . . . ?
C18 C14 C15 C16 0.7(5) . . . . ?
C14 C15 C16 C17 0.7(6) . . . . ?
C18 N1 C17 C16 2.4(5) . . . . ?
Cu1 N1 C17 C16 -177.2(3) . . . . ?
C15 C16 C17 N1 -2.3(6) . . . . ?
C14 C13 C12 C11 0.7(6) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_6-3
_database_code_depnum_ccdc_archive 'CCDC 1445807'
_audit_update_record             
;
2016-10-19 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 Cu N4 O5'
_chemical_formula_sum            'C18 H16 Cu N4 O5'
_chemical_formula_weight         431.89

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

loop_
_symmetry_equiv_pos_as_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                   7.854(3)
_cell_length_b                   10.712(3)
_cell_length_c                   21.440(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.575(6)
_cell_angle_gamma                90.00
_cell_volume                     1788.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4770
_cell_measurement_theta_min      26.37
_cell_measurement_theta_max      2.66

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             884
_exptl_absorpt_coefficient_mu    1.261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7776
_exptl_absorpt_correction_T_max  0.8634
_exptl_absorpt_process_details   'SADABS (Bruker, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12597
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3642
_reflns_number_gt                3027
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.7703P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3642
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.81395(4) 0.61897(3) 0.079419(13) 0.03459(13) Uani 1 1 d . . .
O3 O 0.8444(2) 0.73569(17) 0.15125(8) 0.0437(4) Uani 1 1 d . . .
O1 O 0.7226(3) 0.75262(17) 0.02284(9) 0.0451(4) Uani 1 1 d . . .
N2 N 0.7539(2) 0.52261(19) 0.00313(9) 0.0332(4) Uani 1 1 d . . .
N3 N 0.6673(3) 0.5902(2) -0.04637(10) 0.0368(5) Uani 1 1 d . . .
H3 H 0.6247 0.5590 -0.0820 0.044 Uiso 1 1 calc R . .
N1 N 0.9463(3) 0.4745(2) 0.12388(10) 0.0391(5) Uani 1 1 d . . .
C7 C 0.6593(3) 0.7094(2) -0.03102(11) 0.0333(5) Uani 1 1 d . . .
O4 O 1.0019(4) 0.8779(2) 0.20006(12) 0.0754(8) Uani 1 1 d . . .
O2 O 0.5639(2) 0.5673(2) 0.11824(9) 0.0502(5) Uani 1 1 d . . .
N11 N 0.9815(3) 0.8019(2) 0.15752(11) 0.0478(6) Uani 1 1 d . . .
C6 C 0.5713(3) 0.7975(2) -0.07834(12) 0.0368(5) Uani 1 1 d . . .
C17 C 0.9446(3) 0.3535(2) 0.10185(12) 0.0354(5) Uani 1 1 d . . .
C5 C 0.4879(4) 0.7579(3) -0.13647(12) 0.0449(6) Uani 1 1 d . . .
H5 H 0.4904 0.6740 -0.1476 0.054 Uiso 1 1 calc R . .
C16 C 1.0322(4) 0.4976(3) 0.18018(14) 0.0528(7) Uani 1 1 d . . .
H16 H 1.0317 0.5790 0.1951 0.063 Uiso 1 1 calc R . .
C13 C 1.0306(3) 0.2572(3) 0.13946(14) 0.0448(6) Uani 1 1 d . . .
C9 C 0.8566(3) 0.3196(2) 0.04158(13) 0.0394(6) Uani 1 1 d . . .
C4 C 0.4017(4) 0.8426(3) -0.17749(14) 0.0566(8) Uani 1 1 d . . .
H4 H 0.3445 0.8150 -0.2158 0.068 Uiso 1 1 calc R . .
C8 C 0.7717(3) 0.4053(2) -0.00525(12) 0.0387(6) Uani 1 1 d . . .
H8 H 0.7271 0.3723 -0.0441 0.046 Uiso 1 1 calc R . .
C12 C 1.0227(4) 0.1324(3) 0.11838(17) 0.0566(8) Uani 1 1 d . . .
H12 H 1.0806 0.0706 0.1432 0.068 Uiso 1 1 calc R . .
C3 C 0.3991(4) 0.9675(3) -0.16254(15) 0.0586(8) Uani 1 1 d . . .
H3A H 0.3407 1.0239 -0.1906 0.070 Uiso 1 1 calc R . .
C1 C 0.5686(4) 0.9238(3) -0.06347(14) 0.0500(7) Uani 1 1 d . . .
H1 H 0.6240 0.9517 -0.0250 0.060 Uiso 1 1 calc R . .
C14 C 1.1229(4) 0.2900(3) 0.19812(14) 0.0527(7) Uani 1 1 d . . .
H14 H 1.1837 0.2292 0.2228 0.063 Uiso 1 1 calc R . .
C15 C 1.1232(4) 0.4085(3) 0.21848(15) 0.0617(9) Uani 1 1 d . . .
H15 H 1.1829 0.4307 0.2573 0.074 Uiso 1 1 calc R . .
C11 C 0.9319(5) 0.1013(3) 0.06249(18) 0.0617(9) Uani 1 1 d . . .
H11 H 0.9221 0.0182 0.0500 0.074 Uiso 1 1 calc R . .
C10 C 0.8532(4) 0.1949(3) 0.02374(15) 0.0517(7) Uani 1 1 d . . .
H10 H 0.7962 0.1730 -0.0155 0.062 Uiso 1 1 calc R . .
O5 O 1.0856(3) 0.7846(3) 0.12083(13) 0.0841(8) Uani 1 1 d . . .
C18 C 0.5015(5) 0.6095(4) 0.17230(17) 0.0670(10) Uani 1 1 d . . .
H18A H 0.3785 0.6026 0.1669 0.101 Uiso 1 1 calc R . .
H18B H 0.5338 0.6952 0.1797 0.101 Uiso 1 1 calc R . .
H18C H 0.5490 0.5599 0.2076 0.101 Uiso 1 1 calc R . .
C2 C 0.4838(5) 1.0085(3) -0.10571(16) 0.0630(9) Uani 1 1 d . . .
H2 H 0.4840 1.0930 -0.0957 0.076 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.939(2) . ?
Cu1 O1 1.9510(18) . ?
Cu1 O3 1.9736(18) . ?
Cu1 N1 2.031(2) . ?
Cu1 O2 2.300(2) . ?
O3 N11 1.282(3) . ?
O1 C7 1.282(3) . ?
N2 C8 1.280(3) . ?
N2 N3 1.387(3) . ?
N3 C7 1.322(3) . ?
N3 H3 0.8600 . ?
N1 C16 1.326(3) . ?
N1 C17 1.379(3) . ?
C7 C6 1.488(3) . ?
O4 N11 1.217(3) . ?
O2 C18 1.392(4) . ?
N11 O5 1.221(4) . ?
C6 C1 1.391(4) . ?
C6 C5 1.395(4) . ?
C17 C13 1.423(4) . ?
C17 C9 1.429(4) . ?
C5 C4 1.378(4) . ?
C5 H5 0.9300 . ?
C16 C15 1.393(4) . ?
C16 H16 0.9300 . ?
C13 C14 1.410(4) . ?
C13 C12 1.411(4) . ?
C9 C10 1.389(4) . ?
C9 C8 1.455(4) . ?
C4 C3 1.377(5) . ?
C4 H4 0.9300 . ?
C8 H8 0.9300 . ?
C12 C11 1.352(5) . ?
C12 H12 0.9300 . ?
C3 C2 1.381(5) . ?
C3 H3A 0.9300 . ?
C1 C2 1.389(4) . ?
C1 H1 0.9300 . ?
C14 C15 1.343(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C11 C10 1.394(4) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 O1 80.65(8) . . ?
N2 Cu1 O3 170.56(8) . . ?
O1 Cu1 O3 90.97(8) . . ?
N2 Cu1 N1 92.44(9) . . ?
O1 Cu1 N1 167.08(9) . . ?
O3 Cu1 N1 96.60(8) . . ?
N2 Cu1 O2 93.04(8) . . ?
O1 Cu1 O2 98.05(8) . . ?
O3 Cu1 O2 83.76(7) . . ?
N1 Cu1 O2 93.18(8) . . ?
N11 O3 Cu1 116.48(18) . . ?
C7 O1 Cu1 111.24(16) . . ?
C8 N2 N3 117.2(2) . . ?
C8 N2 Cu1 128.49(18) . . ?
N3 N2 Cu1 114.06(15) . . ?
C7 N3 N2 110.39(19) . . ?
C7 N3 H3 124.8 . . ?
N2 N3 H3 124.8 . . ?
C16 N1 C17 117.9(2) . . ?
C16 N1 Cu1 116.9(2) . . ?
C17 N1 Cu1 125.06(17) . . ?
O1 C7 N3 123.2(2) . . ?
O1 C7 C6 118.4(2) . . ?
N3 C7 C6 118.4(2) . . ?
C18 O2 Cu1 129.39(18) . . ?
O4 N11 O5 123.5(3) . . ?
O4 N11 O3 118.3(3) . . ?
O5 N11 O3 118.2(3) . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 C7 118.7(2) . . ?
C5 C6 C7 122.5(2) . . ?
N1 C17 C13 120.3(2) . . ?
N1 C17 C9 122.0(2) . . ?
C13 C17 C9 117.7(2) . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
N1 C16 C15 124.7(3) . . ?
N1 C16 H16 117.7 . . ?
C15 C16 H16 117.7 . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 C17 118.4(3) . . ?
C12 C13 C17 120.5(3) . . ?
C10 C9 C17 118.8(3) . . ?
C10 C9 C8 115.2(2) . . ?
C17 C9 C8 125.9(2) . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
N2 C8 C9 124.8(2) . . ?
N2 C8 H8 117.6 . . ?
C9 C8 H8 117.6 . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 118.5(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C9 C10 C11 122.5(3) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?

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
N2 Cu1 O3 N11 -110.1(5) . . . . ?
O1 Cu1 O3 N11 -82.72(17) . . . . ?
N1 Cu1 O3 N11 86.79(17) . . . . ?
O2 Cu1 O3 N11 179.28(17) . . . . ?
N2 Cu1 O1 C7 5.50(17) . . . . ?
O3 Cu1 O1 C7 -170.11(18) . . . . ?
N1 Cu1 O1 C7 63.9(4) . . . . ?
O2 Cu1 O1 C7 -86.28(18) . . . . ?
O1 Cu1 N2 C8 -180.0(2) . . . . ?
O3 Cu1 N2 C8 -152.2(4) . . . . ?
N1 Cu1 N2 C8 11.0(2) . . . . ?
O2 Cu1 N2 C8 -82.3(2) . . . . ?
O1 Cu1 N2 N3 -6.12(16) . . . . ?
O3 Cu1 N2 N3 21.7(6) . . . . ?
N1 Cu1 N2 N3 -175.14(16) . . . . ?
O2 Cu1 N2 N3 91.54(16) . . . . ?
C8 N2 N3 C7 -179.8(2) . . . . ?
Cu1 N2 N3 C7 5.5(2) . . . . ?
N2 Cu1 N1 C16 173.8(2) . . . . ?
O1 Cu1 N1 C16 116.6(4) . . . . ?
O3 Cu1 N1 C16 -8.9(2) . . . . ?
O2 Cu1 N1 C16 -93.0(2) . . . . ?
N2 Cu1 N1 C17 -10.5(2) . . . . ?
O1 Cu1 N1 C17 -67.7(4) . . . . ?
O3 Cu1 N1 C17 166.7(2) . . . . ?
O2 Cu1 N1 C17 82.7(2) . . . . ?
Cu1 O1 C7 N3 -4.3(3) . . . . ?
Cu1 O1 C7 C6 175.16(17) . . . . ?
N2 N3 C7 O1 -0.8(3) . . . . ?
N2 N3 C7 C6 179.8(2) . . . . ?
N2 Cu1 O2 C18 -174.7(3) . . . . ?
O1 Cu1 O2 C18 -93.7(3) . . . . ?
O3 Cu1 O2 C18 -3.6(3) . . . . ?
N1 Cu1 O2 C18 92.7(3) . . . . ?
Cu1 O3 N11 O4 177.60(19) . . . . ?
Cu1 O3 N11 O5 -3.1(3) . . . . ?
O1 C7 C6 C1 3.1(4) . . . . ?
N3 C7 C6 C1 -177.4(2) . . . . ?
O1 C7 C6 C5 -175.3(2) . . . . ?
N3 C7 C6 C5 4.2(4) . . . . ?
C16 N1 C17 C13 1.0(4) . . . . ?
Cu1 N1 C17 C13 -174.61(18) . . . . ?
C16 N1 C17 C9 -179.5(3) . . . . ?
Cu1 N1 C17 C9 4.8(3) . . . . ?
C1 C6 C5 C4 -1.4(4) . . . . ?
C7 C6 C5 C4 177.1(3) . . . . ?
C17 N1 C16 C15 0.9(5) . . . . ?
Cu1 N1 C16 C15 176.9(3) . . . . ?
N1 C17 C13 C14 -2.7(4) . . . . ?
C9 C17 C13 C14 177.9(2) . . . . ?
N1 C17 C13 C12 177.1(2) . . . . ?
C9 C17 C13 C12 -2.4(4) . . . . ?
N1 C17 C9 C10 -176.9(2) . . . . ?
C13 C17 C9 C10 2.6(4) . . . . ?
N1 C17 C9 C8 5.1(4) . . . . ?
C13 C17 C9 C8 -175.5(2) . . . . ?
C6 C5 C4 C3 1.3(5) . . . . ?
N3 N2 C8 C9 -179.1(2) . . . . ?
Cu1 N2 C8 C9 -5.4(4) . . . . ?
C10 C9 C8 N2 176.6(3) . . . . ?
C17 C9 C8 N2 -5.2(4) . . . . ?
C14 C13 C12 C11 179.0(3) . . . . ?
C17 C13 C12 C11 -0.7(5) . . . . ?
C5 C4 C3 C2 -0.1(5) . . . . ?
C5 C6 C1 C2 0.3(4) . . . . ?
C7 C6 C1 C2 -178.3(3) . . . . ?
C12 C13 C14 C15 -177.3(3) . . . . ?
C17 C13 C14 C15 2.5(4) . . . . ?
C13 C14 C15 C16 -0.6(5) . . . . ?
N1 C16 C15 C14 -1.2(5) . . . . ?
C13 C12 C11 C10 3.6(5) . . . . ?
C17 C9 C10 C11 0.2(4) . . . . ?
C8 C9 C10 C11 178.5(3) . . . . ?
C12 C11 C10 C9 -3.4(5) . . . . ?
C4 C3 C2 C1 -1.0(5) . . . . ?
C6 C1 C2 C3 0.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.062
