# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_fid420_1m
_database_code_depnum_ccdc_archive 'CCDC 1033365'
_audit_update_record             
;
2016-03-14 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 Cu N2 O14'
_chemical_formula_weight         589.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.131(5)
_cell_length_b                   10.833(8)
_cell_length_c                   16.834(16)
_cell_angle_alpha                103.207(13)
_cell_angle_beta                 96.130(13)
_cell_angle_gamma                107.927(9)
_cell_volume                     1182.3(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3391
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      26.37

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             606
_exptl_absorpt_coefficient_mu    1.003
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.7665
_exptl_absorpt_correction_T_max  0.8807
_exptl_absorpt_process_details   'Bruker SADABS'

_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 SMART APEX2 CCD'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8849
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4121
_reflns_number_gt                3212
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SSAINT'
_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)+(0.0675P)²+0.0000P] 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         4121
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1094
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.0000 0.5000 0.03699(17) Uani 1 2 d S . .
Cu2 Cu 0.5000 0.5000 0.5000 0.03493(17) Uani 1 2 d S . .
N1 N 0.6449(3) 0.0656(2) 0.41699(14) 0.0347(6) Uani 1 1 d . . .
N2 N 0.5672(3) 0.4837(2) 0.38982(14) 0.0329(5) Uani 1 1 d . . .
O1 O 0.5910(3) 0.1896(2) 0.55859(12) 0.0412(5) Uani 1 1 d . . .
O2 O 0.7665(3) 0.3925(2) 0.54895(14) 0.0509(6) Uani 1 1 d . . .
O3 O 0.6944(3) 0.67923(19) 0.52634(12) 0.0373(5) Uani 1 1 d . . .
O4 O 0.8942(3) 0.8170(2) 0.46880(13) 0.0446(5) Uani 1 1 d . . .
O5 O 0.0466(4) 0.3575(2) 0.16803(14) 0.0535(7) Uani 1 1 d . . .
O6 O 0.1530(3) 0.4695(2) 0.07848(13) 0.0507(6) Uani 1 1 d . . .
O7 O -0.1242(5) 0.2218(2) -0.22579(14) 0.0717(8) Uani 1 1 d . . .
O8 O -0.2109(4) 0.0000(2) -0.25592(14) 0.0503(6) Uani 1 1 d . . .
O9 O -0.4201(4) -0.2294(2) -0.04488(14) 0.0572(7) Uani 1 1 d . . .
O10 O -0.3377(4) -0.1083(3) 0.08644(15) 0.0530(7) Uani 1 1 d . . .
O20 O 0.2425(5) 0.5773(3) 0.2784(2) 0.0628(8) Uani 1 1 d . . .
O30 O -0.1742(4) 0.0051(3) 0.59251(14) 0.0415(5) Uani 1 1 d . . .
O40 O -0.4539(6) -0.3180(3) 0.1383(2) 0.0709(9) Uani 1 1 d . . .
O50 O -0.6819(4) -0.4837(3) -0.05991(17) 0.0656(8) Uani 1 1 d . . .
C1 C -0.0588(4) 0.2401(3) 0.02773(17) 0.0333(6) Uani 1 1 d . . .
C2 C -0.0689(4) 0.2383(3) -0.05498(17) 0.0363(7) Uani 1 1 d . . .
H2 H -0.0115 0.3177 -0.0692 0.044 Uiso 1 1 calc R . .
C3 C -0.1642(4) 0.1185(3) -0.11662(17) 0.0331(6) Uani 1 1 d . . .
C4 C -0.2505(4) 0.0029(3) -0.09502(18) 0.0351(7) Uani 1 1 d . . .
H4 H -0.3120 -0.0780 -0.1364 0.042 Uiso 1 1 calc R . .
C5 C -0.2481(4) 0.0039(3) -0.01305(18) 0.0332(6) Uani 1 1 d . . .
C6 C -0.1509(4) 0.1230(3) 0.04836(18) 0.0339(6) Uani 1 1 d . . .
H6 H -0.1475 0.1243 0.1039 0.041 Uiso 1 1 calc R . .
C7 C 0.0565(4) 0.3672(3) 0.09323(17) 0.0373(7) Uani 1 1 d . . .
C8 C -0.1648(5) 0.1196(3) -0.20419(19) 0.0414(7) Uani 1 1 d . . .
C9 C -0.3454(4) -0.1232(3) 0.00815(18) 0.0360(7) Uani 1 1 d . . .
C10 C 0.7301(4) 0.2002(3) 0.43937(18) 0.0354(7) Uani 1 1 d . . .
C11 C 0.8412(5) 0.2674(4) 0.3912(2) 0.0469(8) Uani 1 1 d . . .
H11 H 0.9009 0.3609 0.4079 0.056 Uiso 1 1 calc R . .
C12 C 0.8617(5) 0.1921(4) 0.3173(2) 0.0588(10) Uani 1 1 d . . .
H12 H 0.9360 0.2346 0.2830 0.071 Uiso 1 1 calc R . .
C13 C 0.7748(5) 0.0570(4) 0.2945(2) 0.0566(9) Uani 1 1 d . . .
H13 H 0.7881 0.0062 0.2442 0.068 Uiso 1 1 calc R . .
C14 C 0.6658(5) -0.0060(4) 0.34568(19) 0.0463(8) Uani 1 1 d . . .
H14 H 0.6065 -0.0995 0.3300 0.056 Uiso 1 1 calc R . .
C15 C 0.6946(4) 0.2679(3) 0.52132(19) 0.0383(7) Uani 1 1 d . . .
C16 C 0.7089(4) 0.5962(3) 0.38672(18) 0.0336(6) Uani 1 1 d . . .
C17 C 0.7851(5) 0.6072(4) 0.3173(2) 0.0467(8) Uani 1 1 d . . .
H17 H 0.8838 0.6863 0.3166 0.056 Uiso 1 1 calc R . .
C18 C 0.7132(6) 0.4989(4) 0.2481(2) 0.0546(9) Uani 1 1 d . . .
H18 H 0.7645 0.5025 0.1999 0.066 Uiso 1 1 calc R . .
C19 C 0.5652(5) 0.3854(4) 0.25085(19) 0.0519(9) Uani 1 1 d . . .
H19 H 0.5125 0.3119 0.2039 0.062 Uiso 1 1 calc R . .
C20 C 0.4951(5) 0.3801(3) 0.32231(18) 0.0446(8) Uani 1 1 d . . .
H20 H 0.3948 0.3023 0.3239 0.054 Uiso 1 1 calc R . .
C21 C 0.7740(4) 0.7078(3) 0.46593(18) 0.0343(6) Uani 1 1 d . . .
H8A H -0.191(6) 0.010(4) -0.300(2) 0.069(13) Uiso 1 1 d . . .
H31 H -0.163(5) -0.054(4) 0.566(2) 0.036(11) Uiso 1 1 d . . .
H22 H 0.228(8) 0.643(6) 0.263(3) 0.10(2) Uiso 1 1 d . . .
H32 H -0.089(6) 0.072(4) 0.580(2) 0.064(11) Uiso 1 1 d . . .
H10A H -0.368(6) -0.162(4) 0.096(2) 0.043(12) Uiso 1 1 d . . .
H52 H -0.722(9) -0.510(6) -0.018(4) 0.13(2) Uiso 1 1 d . . .
H21 H 0.256(8) 0.593(5) 0.324(3) 0.10(2) Uiso 1 1 d . . .
H5A H 0.105(6) 0.431(4) 0.203(3) 0.070(13) Uiso 1 1 d . . .
H51 H -0.622(9) -0.397(6) -0.047(3) 0.12(2) Uiso 1 1 d . . .
H42 H -0.552(9) -0.326(7) 0.159(4) 0.14(3) Uiso 1 1 d . . .
H41 H -0.401(12) -0.380(9) 0.119(5) 0.21(4) Uiso 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
Cu1 O1 1.932(2) . ?
Cu1 O1 1.932(2) 2_656 ?
Cu1 N1 1.959(3) . ?
Cu1 N1 1.959(3) 2_656 ?
Cu2 O3 1.925(2) . ?
Cu2 O3 1.925(2) 2_666 ?
Cu2 N2 1.947(3) 2_666 ?
Cu2 N2 1.947(3) . ?
N1 C14 1.322(4) . ?
N1 C10 1.338(4) . ?
N2 C20 1.324(4) . ?
N2 C16 1.339(4) . ?
O1 C15 1.271(4) . ?
O2 C15 1.240(4) . ?
O3 C21 1.269(3) . ?
O4 C21 1.216(3) . ?
O5 C7 1.295(4) . ?
O6 C7 1.207(3) . ?
O7 C8 1.205(4) . ?
O8 C8 1.306(4) . ?
O9 C9 1.206(4) . ?
O10 C9 1.284(4) . ?
C1 C6 1.378(4) . ?
C1 C2 1.382(4) . ?
C1 C7 1.484(4) . ?
C2 C3 1.383(4) . ?
C3 C4 1.365(4) . ?
C3 C8 1.476(4) . ?
C4 C5 1.375(4) . ?
C5 C6 1.378(4) . ?
C5 C9 1.482(4) . ?
C10 C11 1.366(4) . ?
C10 C15 1.493(4) . ?
C11 C12 1.372(5) . ?
C12 C13 1.344(5) . ?
C13 C14 1.378(5) . ?
C16 C17 1.355(4) . ?
C16 C21 1.497(4) . ?
C17 C18 1.368(5) . ?
C18 C19 1.366(5) . ?
C19 C20 1.357(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.00(7) . 2_656 ?
O1 Cu1 N1 83.31(10) . . ?
O1 Cu1 N1 96.69(10) 2_656 . ?
O1 Cu1 N1 96.69(10) . 2_656 ?
O1 Cu1 N1 83.31(10) 2_656 2_656 ?
N1 Cu1 N1 180.000(1) . 2_656 ?
O3 Cu2 O3 180.0 . 2_666 ?
O3 Cu2 N2 95.83(9) . 2_666 ?
O3 Cu2 N2 84.17(9) 2_666 2_666 ?
O3 Cu2 N2 84.17(9) . . ?
O3 Cu2 N2 95.83(9) 2_666 . ?
N2 Cu2 N2 180.000(1) 2_666 . ?
C14 N1 C10 119.7(3) . . ?
C14 N1 Cu1 128.0(2) . . ?
C10 N1 Cu1 112.29(19) . . ?
C20 N2 C16 119.2(3) . . ?
C20 N2 Cu2 129.3(2) . . ?
C16 N2 Cu2 111.58(19) . . ?
C15 O1 Cu1 114.9(2) . . ?
C21 O3 Cu2 114.39(18) . . ?
C6 C1 C2 119.6(3) . . ?
C6 C1 C7 120.8(3) . . ?
C2 C1 C7 119.6(3) . . ?
C3 C2 C1 120.2(3) . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 C8 122.0(3) . . ?
C2 C3 C8 118.6(3) . . ?
C3 C4 C5 121.1(3) . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 C9 119.7(3) . . ?
C6 C5 C9 120.9(3) . . ?
C5 C6 C1 120.3(3) . . ?
O6 C7 O5 123.0(3) . . ?
O6 C7 C1 123.4(3) . . ?
O5 C7 C1 113.6(3) . . ?
O7 C8 O8 123.1(3) . . ?
O7 C8 C3 122.9(3) . . ?
O8 C8 C3 114.0(3) . . ?
O9 C9 O10 124.9(3) . . ?
O9 C9 C5 121.4(3) . . ?
O10 C9 C5 113.7(3) . . ?
N1 C10 C11 122.2(3) . . ?
N1 C10 C15 113.9(2) . . ?
C11 C10 C15 124.0(3) . . ?
C10 C11 C12 117.6(3) . . ?
C13 C12 C11 120.2(3) . . ?
C12 C13 C14 119.9(3) . . ?
N1 C14 C13 120.4(3) . . ?
O2 C15 O1 124.4(3) . . ?
O2 C15 C10 119.9(3) . . ?
O1 C15 C10 115.6(3) . . ?
N2 C16 C17 122.3(3) . . ?
N2 C16 C21 114.3(2) . . ?
C17 C16 C21 123.4(3) . . ?
C16 C17 C18 118.3(3) . . ?
C17 C18 C19 119.2(3) . . ?
C20 C19 C18 119.8(3) . . ?
N2 C20 C19 121.1(3) . . ?
O4 C21 O3 124.6(3) . . ?
O4 C21 C16 119.9(3) . . ?
O3 C21 C16 115.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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 1555021'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H24 Cu N4 O12'
_chemical_formula_weight         720.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.9068(7)
_cell_length_b                   9.2354(9)
_cell_length_c                   11.0960(10)
_cell_angle_alpha                104.3800(10)
_cell_angle_beta                 106.1680(10)
_cell_angle_gamma                101.9190(10)
_cell_volume                     719.97(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3156
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.64

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             369
_exptl_transmission_factor_min   0.799
_exptl_transmission_factor_max   0.857
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.838
_shelx_estimated_absorpt_T_min   0.799
_shelx_estimated_absorpt_T_max   0.857
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_T_max  0.857
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   'Bruker SADABS'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
"Bruker APEX-II CCD'_diffrn_measurement_method   'Omega scan"
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7126
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.384
_diffrn_reflns_theta_max         29.385
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3597
_reflns_number_gt                3067
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+0.2916P] 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         3597
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 0.5000 0.03401(12) Uani 1 2 d S . P . .
O1 O 0.5170(2) 0.47871(18) 0.28096(16) 0.0393(3) Uani 1 1 d D . . . .
O2 O 0.2718(2) 0.34965(18) 0.07852(15) 0.0423(4) Uani 1 1 d . . . . .
H2A H 0.2834 0.4286 0.0566 0.063 Uiso 1 1 calc R U . . .
O3 O 0.6584(3) 0.3811(2) 0.97166(19) 0.0598(5) Uani 1 1 d . . . . .
O4 O 0.4279(3) 0.2600(2) 0.78597(19) 0.0668(6) Uani 1 1 d . . . . .
O5 O 0.1959(3) 0.0095(2) 0.6696(2) 0.0823(8) Uani 1 1 d . . . . .
H5 H 0.2839 0.0892 0.7047 0.123 Uiso 1 1 calc R U . . .
O6 O 0.0887(2) -0.2003(2) 0.71043(17) 0.0523(4) Uani 1 1 d . . . . .
N1 N 0.2738(2) 0.54449(19) 0.40523(17) 0.0347(4) Uani 1 1 d . . . . .
N2 N 0.3760(2) 0.2733(2) 0.38652(18) 0.0372(4) Uani 1 1 d . . . . .
C1 C 0.1794(3) 0.6210(3) 0.4649(2) 0.0425(5) Uani 1 1 d . . . . .
H1 H 0.2209 0.6584 0.5571 0.051 Uiso 1 1 calc R U . . .
C2 C 0.0200(3) 0.6469(3) 0.3935(3) 0.0481(5) Uani 1 1 d . . . . .
H2 H -0.0431 0.7030 0.4369 0.058 Uiso 1 1 calc R U . . .
C3 C -0.0420(3) 0.5875(3) 0.2574(3) 0.0472(5) Uani 1 1 d . . . . .
H3 H -0.1488 0.6023 0.2074 0.057 Uiso 1 1 calc R U . . .
C4 C 0.0541(3) 0.5063(3) 0.1955(2) 0.0390(5) Uani 1 1 d . . . . .
H4 H 0.0130 0.4654 0.1034 0.047 Uiso 1 1 calc R U . . .
C5 C 0.2120(3) 0.4862(2) 0.2715(2) 0.0322(4) Uani 1 1 d . . . . .
C6 C 0.3271(3) 0.3918(2) 0.2146(2) 0.0339(4) Uani 1 1 d . . . . .
C7 C 0.3052(3) 0.2455(2) 0.2553(2) 0.0341(4) Uani 1 1 d . . . . .
C8 C 0.2147(3) 0.0969(3) 0.1665(2) 0.0424(5) Uani 1 1 d . . . . .
H8 H 0.1672 0.0806 0.0759 0.051 Uiso 1 1 calc R U . . .
C9 C 0.1962(4) -0.0272(3) 0.2149(3) 0.0542(6) Uani 1 1 d . . . . .
H9 H 0.1358 -0.1287 0.1571 0.065 Uiso 1 1 calc R U . . .
C10 C 0.2677(4) 0.0005(3) 0.3493(3) 0.0566(7) Uani 1 1 d . . . . .
H10 H 0.2553 -0.0818 0.3836 0.068 Uiso 1 1 calc R U . . .
C11 C 0.3577(4) 0.1517(3) 0.4320(3) 0.0497(6) Uani 1 1 d . . . . .
H11 H 0.4076 0.1702 0.5228 0.060 Uiso 1 1 calc R U . . .
C12 C 0.5019(3) 0.1215(2) 0.9426(2) 0.0311(4) Uani 1 1 d . . . . .
C13 C 0.3647(3) -0.0239(2) 0.87643(19) 0.0314(4) Uani 1 1 d . . . . .
C14 C 0.3696(3) -0.1392(2) 0.9363(2) 0.0331(4) Uani 1 1 d . . . . .
H14 H 0.2798 -0.2356 0.8918 0.040 Uiso 1 1 calc R U . . .
C15 C 0.5311(3) 0.2655(2) 0.8986(2) 0.0368(4) Uani 1 1 d . . . . .
C16 C 0.2053(3) -0.0770(3) 0.7445(2) 0.0403(5) Uani 1 1 d . . . . .
H1A H 0.542(5) 0.560(3) 0.271(3) 0.075(10) 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 N1 1.9860(17) . ?
Cu1 N1 1.9861(17) 2_666 ?
Cu1 N2 2.0209(18) . ?
Cu1 N2 2.0209(18) 2_666 ?
Cu1 O1 2.4329(16) 2_666 ?
Cu1 O1 2.4329(16) . ?
O1 C6 1.426(3) . ?
O2 C6 1.376(2) . ?
O3 C15 1.217(3) . ?
O4 C15 1.271(3) . ?
O5 C16 1.286(3) . ?
O6 C16 1.204(3) . ?
N1 C1 1.324(3) . ?
N1 C5 1.350(3) . ?
N2 C11 1.339(3) . ?
N2 C7 1.342(3) . ?
C1 C2 1.391(3) . ?
C2 C3 1.374(4) . ?
C3 C4 1.371(3) . ?
C4 C5 1.375(3) . ?
C5 C6 1.536(3) . ?
C6 C7 1.520(3) . ?
C7 C8 1.377(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.375(4) . ?
C10 C11 1.374(4) . ?
C12 C14 1.388(3) 2_657 ?
C12 C13 1.409(3) . ?
C12 C15 1.522(3) . ?
C13 C14 1.389(3) . ?
C13 C16 1.528(3) . ?
C14 C12 1.388(3) 2_657 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 180.00(9) . 2_666 ?
N1 Cu1 N2 87.21(7) . . ?
N1 Cu1 N2 92.79(7) 2_666 . ?
N1 Cu1 N2 92.79(7) . 2_666 ?
N1 Cu1 N2 87.21(7) 2_666 2_666 ?
N2 Cu1 N2 180.0 . 2_666 ?
N1 Cu1 O1 104.09(6) . 2_666 ?
N1 Cu1 O1 75.91(6) 2_666 2_666 ?
N2 Cu1 O1 106.75(6) . 2_666 ?
N2 Cu1 O1 73.25(6) 2_666 2_666 ?
N1 Cu1 O1 75.91(6) . . ?
N1 Cu1 O1 104.09(6) 2_666 . ?
N2 Cu1 O1 73.25(6) . . ?
N2 Cu1 O1 106.75(6) 2_666 . ?
O1 Cu1 O1 180.0 2_666 . ?
C6 O1 Cu1 93.26(11) . . ?
C1 N1 C5 119.45(18) . . ?
C1 N1 Cu1 124.28(15) . . ?
C5 N1 Cu1 116.22(14) . . ?
C11 N2 C7 118.5(2) . . ?
C11 N2 Cu1 125.36(17) . . ?
C7 N2 Cu1 116.17(13) . . ?
N1 C1 C2 121.9(2) . . ?
C3 C2 C1 118.3(2) . . ?
C4 C3 C2 119.9(2) . . ?
C3 C4 C5 119.1(2) . . ?
N1 C5 C4 121.3(2) . . ?
N1 C5 C6 114.45(17) . . ?
C4 C5 C6 124.15(19) . . ?
O2 C6 O1 113.85(17) . . ?
O2 C6 C7 109.47(16) . . ?
O1 C6 C7 105.00(15) . . ?
O2 C6 C5 112.43(16) . . ?
O1 C6 C5 108.21(16) . . ?
C7 C6 C5 107.45(16) . . ?
N2 C7 C8 122.39(19) . . ?
N2 C7 C6 114.25(17) . . ?
C8 C7 C6 123.32(19) . . ?
C7 C8 C9 118.5(2) . . ?
C10 C9 C8 119.5(2) . . ?
C11 C10 C9 118.8(2) . . ?
N2 C11 C10 122.3(2) . . ?
C14 C12 C13 117.36(17) 2_657 . ?
C14 C12 C15 114.11(18) 2_657 . ?
C13 C12 C15 128.53(18) . . ?
C14 C13 C12 117.67(18) . . ?
C14 C13 C16 113.01(18) . . ?
C12 C13 C16 129.32(17) . . ?
C12 C14 C13 124.97(19) 2_657 . ?
O3 C15 O4 122.08(19) . . ?
O3 C15 C12 118.18(19) . . ?
O4 C15 C12 119.69(19) . . ?
O6 C16 O5 120.0(2) . . ?
O6 C16 C13 119.85(19) . . ?
O5 C16 C13 120.15(19) . . ?

_refine_diff_density_max         0.562
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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 1555022'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 Cu0.50 N2 O7'
_chemical_formula_weight         415.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   21.289(3)
_cell_length_b                   10.6498(16)
_cell_length_c                   15.634(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.939(2)
_cell_angle_gamma                90
_cell_volume                     3408.3(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7868
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.97

_exptl_crystal_description       plate
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_F_000             1708
_exptl_transmission_factor_min   0.724
_exptl_transmission_factor_max   0.781
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.724
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_T_max  0.781
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   'Bruker SADABS'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex-II CCD'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20891
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.396
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4079
_reflns_number_gt                3417
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+2.3036P] 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         4079
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0850
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.0000 0.0000 0.02598(9) Uani 1 2 d S . P . .
O1 O -0.07512(6) 0.15862(10) 0.00661(7) 0.0293(2) Uani 1 1 d . . . . .
O2 O -0.05403(6) 0.37228(10) 0.02799(8) 0.0371(3) Uani 1 1 d . . . . .
H2A H -0.0816 0.3901 -0.0184 0.056 Uiso 1 1 calc R U . . .
O3 O 0.14804(7) 0.57817(11) 0.12476(8) 0.0439(3) Uani 1 1 d . . . . .
O4 O 0.15219(6) 0.78472(11) 0.14652(8) 0.0407(3) Uani 1 1 d . . . . .
O5 O 0.28710(7) 0.40622(12) 0.52435(8) 0.0443(3) Uani 1 1 d . . . . .
H5A H 0.2833 0.3369 0.5452 0.067 Uiso 1 1 calc R U . . .
O6 O 0.21400(7) 0.32620(12) 0.40764(8) 0.0473(3) Uani 1 1 d . . . . .
O7 O 0.32694(7) 0.84023(13) 0.43755(9) 0.0491(4) Uani 1 1 d . . . . .
H7A H 0.3233 0.9021 0.4053 0.074 Uiso 1 1 calc R U . . .
N1 N 0.04448(7) 0.10418(12) 0.10817(8) 0.0276(3) Uani 1 1 d . . . . .
N2 N 0.02286(7) 0.13504(12) -0.07355(8) 0.0281(3) Uani 1 1 d . . . . .
C1 C 0.09089(8) 0.06440(16) 0.17959(10) 0.0341(4) Uani 1 1 d . . . . .
H1 H 0.1068 -0.0170 0.1803 0.041 Uiso 1 1 calc R U . . .
C2 C 0.11559(9) 0.14116(17) 0.25203(11) 0.0384(4) Uani 1 1 d . . . . .
H2 H 0.1477 0.1118 0.3011 0.046 Uiso 1 1 calc R U . . .
C3 C 0.09218(9) 0.26164(17) 0.25074(11) 0.0392(4) Uani 1 1 d . . . . .
H3 H 0.1073 0.3140 0.2997 0.047 Uiso 1 1 calc R U . . .
C4 C 0.04588(9) 0.30418(16) 0.17576(10) 0.0346(4) Uani 1 1 d . . . . .
H4 H 0.0307 0.3864 0.1727 0.042 Uiso 1 1 calc R U . . .
C5 C 0.02282(8) 0.22271(14) 0.10596(9) 0.0262(3) Uani 1 1 d . . . . .
C6 C -0.02827(8) 0.25557(13) 0.01985(10) 0.0270(3) Uani 1 1 d . . . . .
C7 C 0.00668(8) 0.25091(14) -0.05427(10) 0.0278(3) Uani 1 1 d . . . . .
C8 C 0.02559(9) 0.35531(16) -0.09302(11) 0.0389(4) Uani 1 1 d . . . . .
H8 H 0.0143 0.4355 -0.0789 0.047 Uiso 1 1 calc R U . . .
C9 C 0.06167(11) 0.33821(19) -0.15329(13) 0.0483(5) Uani 1 1 d . . . . .
H9 H 0.0751 0.4075 -0.1800 0.058 Uiso 1 1 calc R U . . .
C10 C 0.07778(10) 0.2194(2) -0.17396(13) 0.0465(5) Uani 1 1 d . . . . .
H10 H 0.1017 0.2068 -0.2149 0.056 Uiso 1 1 calc R U . . .
C11 C 0.05754(9) 0.11921(18) -0.13245(11) 0.0381(4) Uani 1 1 d . . . . .
H11 H 0.0683 0.0382 -0.1457 0.046 Uiso 1 1 calc R U . . .
C12 C 0.25052(8) 0.53436(16) 0.39674(10) 0.0294(3) Uani 1 1 d . . . . .
C13 C 0.21271(8) 0.54528(15) 0.30872(10) 0.0276(3) Uani 1 1 d . . . . .
H13 H 0.1884 0.4772 0.2802 0.033 Uiso 1 1 calc R U . . .
C14 C 0.21150(7) 0.65809(14) 0.26405(10) 0.0270(3) Uani 1 1 d . . . . .
C15 C 0.24826(8) 0.75924(15) 0.30686(10) 0.0312(3) Uani 1 1 d . . . . .
H15 H 0.2464 0.8355 0.2773 0.037 Uiso 1 1 calc R U . . .
C16 C 0.28776(8) 0.74713(16) 0.39348(11) 0.0330(3) Uani 1 1 d . . . . .
C17 C 0.28826(8) 0.63411(16) 0.43871(10) 0.0337(4) Uani 1 1 d . . . . .
H17 H 0.3140 0.6258 0.4970 0.040 Uiso 1 1 calc R U . . .
C18 C 0.24906(8) 0.41328(16) 0.44385(10) 0.0316(3) Uani 1 1 d . . . . .
C19 C 0.16750(8) 0.67415(15) 0.17065(10) 0.0297(3) Uani 1 1 d . . . . .
H1A H -0.1045(11) 0.174(2) -0.0419(15) 0.046(6) Uiso 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
Cu1 N2 1.9836(13) 5 ?
Cu1 N2 1.9836(13) . ?
Cu1 N1 2.0268(12) . ?
Cu1 N1 2.0268(12) 5 ?
Cu1 O1 2.3479(12) . ?
Cu1 O1 2.3479(12) 5 ?
O1 C6 1.4107(19) . ?
O2 C6 1.3785(18) . ?
O3 C19 1.252(2) . ?
O4 C19 1.2520(19) . ?
O5 C18 1.2983(19) . ?
O6 C18 1.227(2) . ?
O7 C16 1.356(2) . ?
N1 C5 1.3411(19) . ?
N1 C1 1.3404(19) . ?
N2 C7 1.338(2) . ?
N2 C11 1.340(2) . ?
C1 C2 1.378(2) . ?
C2 C3 1.375(3) . ?
C3 C4 1.384(2) . ?
C4 C5 1.375(2) . ?
C5 C6 1.521(2) . ?
C6 C7 1.540(2) . ?
C7 C8 1.378(2) . ?
C8 C9 1.381(3) . ?
C9 C10 1.373(3) . ?
C10 C11 1.378(3) . ?
C12 C17 1.384(2) . ?
C12 C13 1.395(2) . ?
C12 C18 1.490(2) . ?
C13 C14 1.386(2) . ?
C14 C15 1.390(2) . ?
C14 C19 1.513(2) . ?
C15 C16 1.390(2) . ?
C16 C17 1.395(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N2 180.0 5 . ?
N2 Cu1 N1 92.64(5) 5 . ?
N2 Cu1 N1 87.36(5) . . ?
N2 Cu1 N1 87.36(5) 5 5 ?
N2 Cu1 N1 92.64(5) . 5 ?
N1 Cu1 N1 180.00(5) . 5 ?
N2 Cu1 O1 102.57(5) 5 . ?
N2 Cu1 O1 77.43(5) . . ?
N1 Cu1 O1 74.76(5) . . ?
N1 Cu1 O1 105.24(5) 5 . ?
N2 Cu1 O1 77.43(5) 5 5 ?
N2 Cu1 O1 102.56(5) . 5 ?
N1 Cu1 O1 105.24(5) . 5 ?
N1 Cu1 O1 74.76(5) 5 5 ?
O1 Cu1 O1 180.0 . 5 ?
C6 O1 Cu1 94.04(9) . . ?
C5 N1 C1 119.24(13) . . ?
C5 N1 Cu1 114.54(9) . . ?
C1 N1 Cu1 126.20(11) . . ?
C7 N2 C11 119.71(14) . . ?
C7 N2 Cu1 114.76(10) . . ?
C11 N2 Cu1 125.20(11) . . ?
N1 C1 C2 121.64(16) . . ?
C3 C2 C1 119.11(15) . . ?
C2 C3 C4 119.27(15) . . ?
C5 C4 C3 118.79(16) . . ?
N1 C5 C4 121.89(14) . . ?
N1 C5 C6 113.37(12) . . ?
C4 C5 C6 124.75(14) . . ?
O2 C6 O1 112.98(13) . . ?
O2 C6 C5 109.37(12) . . ?
O1 C6 C5 105.45(12) . . ?
O2 C6 C7 112.65(12) . . ?
O1 C6 C7 109.52(12) . . ?
C5 C6 C7 106.42(13) . . ?
N2 C7 C8 121.39(15) . . ?
N2 C7 C6 114.00(12) . . ?
C8 C7 C6 124.37(14) . . ?
C7 C8 C9 118.54(17) . . ?
C10 C9 C8 120.25(16) . . ?
C9 C10 C11 118.17(18) . . ?
N2 C11 C10 121.94(17) . . ?
C17 C12 C13 120.41(15) . . ?
C17 C12 C18 121.22(14) . . ?
C13 C12 C18 118.37(15) . . ?
C14 C13 C12 119.67(15) . . ?
C13 C14 C15 119.93(14) . . ?
C13 C14 C19 120.35(14) . . ?
C15 C14 C19 119.64(14) . . ?
C14 C15 C16 120.46(14) . . ?
O7 C16 C15 123.40(15) . . ?
O7 C16 C17 117.10(14) . . ?
C15 C16 C17 119.50(15) . . ?
C12 C17 C16 119.97(14) . . ?
O6 C18 O5 122.82(15) . . ?
O6 C18 C12 121.25(14) . . ?
O5 C18 C12 115.93(14) . . ?
O3 C19 O4 125.26(14) . . ?
O3 C19 C14 118.72(14) . . ?
O4 C19 C14 115.99(14) . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_fid420h_1
_database_code_depnum_ccdc_archive 'CCDC 1033364'
_audit_update_record             
;
2016-03-14 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 Cu2 N2 O9'
_chemical_formula_weight         553.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   15.436(2)
_cell_length_b                   10.2155(17)
_cell_length_c                   12.2521(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1932.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5661
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      29.28

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    2.263
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.5501
_exptl_absorpt_correction_T_max  0.6731
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 SMART APEX2 CCD'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4462
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2250
_reflns_number_gt                2180
_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)+(0.0470P)²+0.0473P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.43(2)
_refine_ls_number_reflns         2250
_refine_ls_number_parameters     311
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0643
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.070
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0252(3) 0.8432(5) 0.3264(4) 0.0394(12) Uani 1 1 d . . .
H1 H 0.0219 0.8306 0.2801 0.047 Uiso 1 1 calc R . .
C2 C -0.0911(4) 0.9237(4) 0.2925(4) 0.0429(13) Uani 1 1 d . . .
H2 H -0.0879 0.9676 0.2261 0.051 Uiso 1 1 calc R . .
C9 C -0.1410(4) 0.9606(5) 0.8215(6) 0.0586(16) Uani 1 1 d . . .
H9 H -0.1751 1.0338 0.8354 0.070 Uiso 1 1 calc R . .
C10 C -0.0925(4) 0.9058(5) 0.9041(5) 0.0482(13) Uani 1 1 d . . .
H10 H -0.0925 0.9418 0.9738 0.058 Uiso 1 1 calc R . .
C11 C -0.0444(4) 0.7971(5) 0.8809(4) 0.0413(11) Uani 1 1 d . . .
H11 H -0.0128 0.7578 0.9366 0.050 Uiso 1 1 calc R . .
C19 C 0.3576(2) 0.9398(4) 1.0990(3) 0.0207(8) Uani 1 1 d . . .
C20 C 0.1416(3) 0.6400(4) 1.2754(3) 0.0248(9) Uani 1 1 d . . .
O5 O 0.14480(19) 0.7075(3) 1.3610(2) 0.0254(6) Uani 1 1 d . . .
O6 O 0.1033(2) 0.5307(3) 1.2677(3) 0.0450(8) Uani 1 1 d . . .
O7 O 0.4025(2) 0.9428(3) 1.1831(2) 0.0302(7) Uani 1 1 d . . .
O8 O 0.3610(2) 1.0181(3) 1.0201(3) 0.0380(8) Uani 1 1 d . . .
O9 O 0.1414(3) 0.8240(4) 0.5830(4) 0.0432(9) Uani 1 1 d . . .
H91 H 0.151(4) 0.782(6) 0.642(7) 0.058(19) Uiso 1 1 d . . .
H21 H -0.162(3) 0.603(4) 0.646(4) 0.015(12) Uiso 1 1 d . . .
H92 H 0.180(4) 0.838(6) 0.571(6) 0.05(3) Uiso 1 1 d . . .
C3 C -0.1616(3) 0.9374(4) 0.3590(5) 0.0411(12) Uani 1 1 d . . .
H3 H -0.2069 0.9922 0.3387 0.049 Uiso 1 1 calc R . .
C4 C -0.1654(3) 0.8690(4) 0.4573(4) 0.0373(11) Uani 1 1 d . . .
H4 H -0.2143 0.8733 0.5014 0.045 Uiso 1 1 calc R . .
C5 C -0.0948(3) 0.7951(4) 0.4875(4) 0.0289(9) Uani 1 1 d . . .
C6 C -0.0904(2) 0.7159(4) 0.5934(4) 0.0269(9) Uani 1 1 d . . .
C7 C -0.0891(3) 0.7968(4) 0.6993(4) 0.0325(10) Uani 1 1 d . . .
C8 C -0.1389(4) 0.9073(4) 0.7188(5) 0.0495(14) Uani 1 1 d . . .
H8 H -0.1707 0.9451 0.6625 0.059 Uiso 1 1 calc R . .
C12 C 0.1505(3) 0.6813(4) 0.8701(4) 0.0295(10) Uani 1 1 d . . .
C13 C 0.1877(3) 0.7127(3) 0.9808(4) 0.0256(8) Uani 1 1 d . . .
C14 C 0.2559(3) 0.8020(3) 0.9891(4) 0.0252(8) Uani 1 1 d . . .
H14 H 0.2797 0.8384 0.9264 0.030 Uiso 1 1 calc R . .
C15 C 0.2879(3) 0.8365(3) 1.0909(4) 0.0220(8) Uani 1 1 d . . .
C16 C 0.2530(3) 0.7825(3) 1.1846(3) 0.0212(8) Uani 1 1 d . . .
H16 H 0.2749 0.8052 1.2527 0.025 Uiso 1 1 calc R . .
C17 C 0.1843(3) 0.6933(3) 1.1764(3) 0.0225(9) Uani 1 1 d . . .
C18 C 0.1536(3) 0.6587(3) 1.0741(4) 0.0231(9) Uani 1 1 d . . .
H18 H 0.1091 0.5978 1.0685 0.028 Uiso 1 1 calc R . .
N1 N -0.0255(2) 0.7822(3) 0.4228(3) 0.0294(8) Uani 1 1 d . . .
N2 N -0.0414(3) 0.7442(3) 0.7786(3) 0.0320(8) Uani 1 1 d . . .
O1 O -0.01886(16) 0.6342(3) 0.5919(2) 0.0234(6) Uani 1 1 d . . .
O2 O -0.1682(2) 0.6432(3) 0.5971(4) 0.0373(8) Uani 1 1 d . . .
O3 O 0.0916(2) 0.5915(3) 0.8707(3) 0.0344(7) Uani 1 1 d . . .
O4 O 0.1736(2) 0.7425(3) 0.7905(3) 0.0457(9) Uani 1 1 d . . .
Cu1 Cu 0.06614(3) 0.66371(4) 0.47865(4) 0.02317(13) Uani 1 1 d . . .
Cu2 Cu 0.02853(3) 0.59038(4) 0.73437(4) 0.02338(13) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.336(6) . ?
C1 C2 1.373(7) . ?
C2 C3 1.366(8) . ?
C9 C8 1.372(9) . ?
C9 C10 1.377(9) . ?
C10 C11 1.365(7) . ?
C11 N2 1.365(6) . ?
C19 O7 1.242(5) . ?
C19 O8 1.256(5) . ?
C19 C15 1.510(5) . ?
C20 O5 1.256(5) . ?
C20 O6 1.267(5) . ?
C20 C17 1.484(6) . ?
O5 Cu1 1.937(3) 1_556 ?
O6 Cu2 2.416(3) 2_565 ?
O7 Cu2 1.950(3) 4 ?
O8 Cu1 1.933(3) 4 ?
O9 Cu1 2.380(4) . ?
C3 C4 1.393(7) . ?
C4 C5 1.377(6) . ?
C5 N1 1.339(6) . ?
C5 C6 1.530(7) . ?
C6 O1 1.384(5) . ?
C6 O2 1.413(5) . ?
C6 C7 1.539(6) . ?
C7 N2 1.333(6) . ?
C7 C8 1.387(6) . ?
C12 O4 1.213(6) . ?
C12 O3 1.291(5) . ?
C12 C13 1.508(6) . ?
C13 C18 1.374(6) . ?
C13 C14 1.397(6) . ?
C14 C15 1.387(6) . ?
C15 C16 1.384(6) . ?
C16 C17 1.402(5) . ?
C17 C18 1.385(6) . ?
N1 Cu1 1.983(3) . ?
N2 Cu2 1.982(4) . ?
O1 Cu1 1.934(3) . ?
O1 Cu2 1.944(3) . ?
O3 Cu2 1.934(3) . ?
Cu1 O8 1.933(3) 4_544 ?
Cu1 O5 1.937(3) 1_554 ?
Cu2 O7 1.950(3) 4_544 ?
Cu2 O6 2.416(3) 2_564 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.0(5) . . ?
C3 C2 C1 118.1(5) . . ?
C8 C9 C10 120.0(5) . . ?
C11 C10 C9 118.2(5) . . ?
N2 C11 C10 122.1(5) . . ?
O7 C19 O8 126.8(3) . . ?
O7 C19 C15 118.0(3) . . ?
O8 C19 C15 115.1(4) . . ?
O5 C20 O6 124.3(4) . . ?
O5 C20 C17 117.7(3) . . ?
O6 C20 C17 118.0(4) . . ?
C20 O5 Cu1 118.0(3) . 1_556 ?
C20 O6 Cu2 148.9(3) . 2_565 ?
C19 O7 Cu2 126.3(3) . 4 ?
C19 O8 Cu1 135.8(3) . 4 ?
C2 C3 C4 119.9(4) . . ?
C5 C4 C3 118.3(5) . . ?
N1 C5 C4 121.8(5) . . ?
N1 C5 C6 114.5(3) . . ?
C4 C5 C6 123.6(4) . . ?
O1 C6 O2 111.3(3) . . ?
O1 C6 C5 110.1(4) . . ?
O2 C6 C5 105.5(4) . . ?
O1 C6 C7 108.9(4) . . ?
O2 C6 C7 105.4(4) . . ?
C5 C6 C7 115.5(3) . . ?
N2 C7 C8 120.6(5) . . ?
N2 C7 C6 113.9(4) . . ?
C8 C7 C6 125.2(5) . . ?
C9 C8 C7 119.6(5) . . ?
O4 C12 O3 125.3(4) . . ?
O4 C12 C13 120.1(4) . . ?
O3 C12 C13 114.5(4) . . ?
C18 C13 C14 119.4(4) . . ?
C18 C13 C12 121.2(3) . . ?
C14 C13 C12 119.4(4) . . ?
C15 C14 C13 120.0(4) . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 C19 120.1(4) . . ?
C14 C15 C19 119.4(4) . . ?
C15 C16 C17 119.7(4) . . ?
C18 C17 C16 119.3(4) . . ?
C18 C17 C20 119.6(4) . . ?
C16 C17 C20 121.0(4) . . ?
C13 C18 C17 121.3(4) . . ?
C5 N1 C1 118.8(4) . . ?
C5 N1 Cu1 115.2(3) . . ?
C1 N1 Cu1 126.0(3) . . ?
C7 N2 C11 119.4(4) . . ?
C7 N2 Cu2 114.9(3) . . ?
C11 N2 Cu2 125.7(4) . . ?
C6 O1 Cu1 117.2(3) . . ?
C6 O1 Cu2 115.3(3) . . ?
Cu1 O1 Cu2 115.14(13) . . ?
C12 O3 Cu2 110.7(3) . . ?
O8 Cu1 O1 94.95(12) 4_544 . ?
O8 Cu1 O5 90.48(12) 4_544 1_554 ?
O1 Cu1 O5 174.57(12) . 1_554 ?
O8 Cu1 N1 167.24(15) 4_544 . ?
O1 Cu1 N1 81.90(14) . . ?
O5 Cu1 N1 92.82(14) 1_554 . ?
O8 Cu1 O9 95.97(15) 4_544 . ?
O1 Cu1 O9 93.04(16) . . ?
O5 Cu1 O9 86.26(15) 1_554 . ?
N1 Cu1 O9 96.54(15) . . ?
O3 Cu2 O1 164.45(12) . . ?
O3 Cu2 O7 90.45(12) . 4_544 ?
O1 Cu2 O7 95.41(12) . 4_544 ?
O3 Cu2 N2 91.89(15) . . ?
O1 Cu2 N2 81.84(14) . . ?
O7 Cu2 N2 176.98(15) 4_544 . ?
O3 Cu2 O6 106.33(13) . 2_564 ?
O1 Cu2 O6 87.29(12) . 2_564 ?
O7 Cu2 O6 96.82(12) 4_544 2_564 ?
N2 Cu2 O6 84.33(14) . 2_564 ?

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.951
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.064
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_fid1072h_n_0m
_database_code_depnum_ccdc_archive 'CCDC 1555020'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H34 Cu4 N4 O21'
_chemical_formula_weight         1232.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   23.644(3)
_cell_length_b                   11.6083(16)
_cell_length_c                   18.180(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.0070(10)
_cell_angle_gamma                90.00
_cell_volume                     4363.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.66

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2488
_exptl_absorpt_coefficient_mu    2.019
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.6428
_exptl_absorpt_correction_T_max  0.8391
_exptl_absorpt_process_details   'Bruker SADABS'

_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       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26547
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         28.73
_reflns_number_total             5557
_reflns_number_gt                4929
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0400P)²+4.1530P] 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         5557
_refine_ls_number_parameters     358
_refine_ls_number_restraints     325
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.030
_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 0.193089(10) 0.683586(18) 0.252167(12) 0.02506(7) Uani 1 1 d U . .
Cu2 Cu 0.314280(10) 0.62869(2) 0.225789(13) 0.02962(7) Uani 1 1 d U . .
O3 O 0.26497(6) 0.66389(12) 0.36443(8) 0.0343(3) Uani 1 1 d U . .
O1 O 0.22830(6) 0.57616(10) 0.20112(7) 0.0258(2) Uani 1 1 d U . .
N2 N 0.27595(8) 0.62317(13) 0.10294(10) 0.0289(3) Uani 1 1 d U . .
O5 O 0.14878(7) 0.75326(12) 0.30923(9) 0.0345(3) Uani 1 1 d U . .
N1 N 0.11545(7) 0.67155(13) 0.14040(10) 0.0300(3) Uani 1 1 d U . .
O4 O 0.34931(7) 0.62222(15) 0.34507(9) 0.0435(4) Uani 1 1 d U . .
O7 O 0.39353(7) 0.70418(14) 0.24188(10) 0.0423(3) Uani 1 1 d U . .
C12 C 0.13829(8) 0.86046(16) 0.31255(11) 0.0278(3) Uani 1 1 d U . .
C23 C 0.5000 0.8160(2) 0.2500 0.0276(5) Uani 1 2 d SU . .
O6 O 0.14060(8) 0.93482(12) 0.26508(10) 0.0436(4) Uani 1 1 d U . .
C18 C 0.11986(8) 0.89471(15) 0.37792(11) 0.0268(3) Uani 1 1 d U . .
O8 O 0.35463(8) 0.86831(16) 0.26318(12) 0.0527(4) Uani 1 1 d U . .
C15 C 0.08480(9) 0.96799(17) 0.49564(12) 0.0321(4) Uani 1 1 d U . .
H15A H 0.0727 0.9909 0.5351 0.039 Uiso 1 1 calc R . .
O11 O 0.21785(8) 0.84417(13) 0.20087(9) 0.0410(3) Uani 1 1 d U . .
H11A H 0.1973 0.8993 0.2037 0.062 Uiso 1 1 calc R . .
H11B H 0.2557 0.8604 0.2211 0.062 Uiso 1 1 d R . .
C24 C 0.39504(9) 0.81263(18) 0.25292(12) 0.0344(4) Uani 1 1 d U . .
C10 C 0.28288(12) 0.6212(2) -0.02323(14) 0.0438(5) Uani 1 1 d U . .
H10D H 0.3037 0.6443 -0.0529 0.053 Uiso 1 1 calc R . .
C5 C 0.12234(9) 0.60647(17) 0.08507(12) 0.0333(4) Uani 1 1 d U . .
C7 C 0.21994(9) 0.56605(16) 0.06477(11) 0.0304(4) Uani 1 1 d U . .
C13 C 0.15396(8) 0.85474(15) 0.45983(11) 0.0260(3) Uani 1 1 d U . .
H13A H 0.1874 0.8019 0.4750 0.031 Uiso 1 1 calc R . .
O9 O -0.00016(10) 1.0795(2) 0.39562(13) 0.0727(6) Uani 1 1 d U . .
H9AA H -0.0247 1.0804 0.3447 0.109 Uiso 1 1 calc R . .
C17 C 0.06951(9) 0.9738(2) 0.35580(12) 0.0369(4) Uani 1 1 d U . .
C16 C 0.05041(9) 1.00666(19) 0.41339(13) 0.0392(4) Uani 1 1 d U . .
C1 C 0.05888(10) 0.7253(2) 0.11715(14) 0.0448(5) Uani 1 1 d U . .
H1A H 0.0547 0.7710 0.1563 0.054 Uiso 1 1 calc R . .
C20 C 0.45006(9) 0.87557(16) 0.25181(13) 0.0319(4) Uani 1 1 d U . .
C9 C 0.22708(12) 0.5575(2) -0.06137(13) 0.0483(6) Uani 1 1 d U . .
H9A H 0.2106 0.5346 -0.1171 0.058 Uiso 1 1 calc R . .
C6 C 0.18750(8) 0.54277(15) 0.11842(11) 0.0278(3) Uani 1 1 d U . .
C11 C 0.30723(10) 0.65009(17) 0.06017(13) 0.0361(4) Uani 1 1 d U . .
H11C H 0.3464 0.6893 0.0876 0.043 Uiso 1 1 calc R . .
C8 C 0.19528(11) 0.5273(2) -0.01735(13) 0.0446(5) Uani 1 1 d U . .
H8A H 0.1582 0.4820 -0.0422 0.053 Uiso 1 1 calc R . .
C4 C 0.07195(12) 0.5924(3) 0.00481(17) 0.0747(10) Uani 1 1 d U . .
H4A H 0.0769 0.5462 -0.0335 0.090 Uiso 1 1 calc R . .
C3 C 0.01377(13) 0.6478(4) -0.01853(18) 0.0841(12) Uani 1 1 d U . .
H3A H -0.0207 0.6389 -0.0726 0.101 Uiso 1 1 calc R . .
C21 C 0.44979(17) 0.9945(2) 0.2512(2) 0.0706(10) Uani 1 1 d U . .
C2 C 0.00752(12) 0.7152(3) 0.03824(17) 0.0622(7) Uani 1 1 d U . .
H2A H -0.0310 0.7536 0.0235 0.075 Uiso 1 1 calc R . .
O10 O 0.47718(17) 1.1685(3) 0.2142(3) 0.0696(14) Uani 0.50 1 d PU . .
H10A H 0.4407 1.1897 0.2078 0.104 Uiso 0.50 1 d PR . .
C22 C 0.48398(19) 1.0531(3) 0.2286(3) 0.0405(11) Uani 0.50 1 d PU . .
H23A H 0.5000 0.736(3) 0.2500 0.040(9) Uiso 1 2 d S . .
H17A H 0.0500(11) 1.007(2) 0.3021(16) 0.041(6) Uiso 1 1 d . . .
O2 O 0.17493(8) 0.42365(12) 0.11060(10) 0.0419(3) Uani 1 1 d U . .
H2B H 0.1659 0.4028 0.1467 0.063 Uiso 1 1 calc R . .
C14 C 0.13739(8) 0.89499(14) 0.51925(11) 0.0252(3) Uani 1 1 d U . .
C19 C 0.32237(8) 0.63379(15) 0.38937(11) 0.0269(3) Uani 1 1 d U . .
H21A H 0.4217(15) 1.030(3) 0.252(2) 0.071(9) Uiso 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
Cu1 O3 1.9344(13) . ?
Cu1 O1 1.9644(12) . ?
Cu1 O5 1.9702(13) . ?
Cu1 N1 1.9749(15) . ?
Cu1 O11 2.2840(15) . ?
Cu2 O4 1.9111(14) . ?
Cu2 O1 1.9548(12) . ?
Cu2 O7 1.9579(14) . ?
Cu2 N2 1.9622(16) . ?
O3 C19 1.254(2) . ?
O1 C6 1.391(2) . ?
N2 C7 1.336(3) . ?
N2 C11 1.344(3) . ?
O5 C12 1.276(2) . ?
N1 C5 1.330(2) . ?
N1 C1 1.345(2) . ?
O4 C19 1.253(2) . ?
O7 C24 1.273(3) . ?
C12 O6 1.240(2) . ?
C12 C18 1.504(2) . ?
C23 C20 1.383(2) 2_655 ?
C23 C20 1.383(2) . ?
C23 H23A 0.93(3) . ?
C18 C13 1.385(2) . ?
C18 C17 1.399(3) . ?
O8 C24 1.240(2) . ?
C15 C16 1.385(3) . ?
C15 C14 1.390(2) . ?
C15 H15A 0.9300 . ?
O11 H11A 0.8200 . ?
O11 H11B 0.8068 . ?
C24 C20 1.501(3) . ?
C10 C9 1.372(4) . ?
C10 C11 1.377(3) . ?
C10 H10D 0.9300 . ?
C5 C4 1.374(3) . ?
C5 C6 1.543(2) . ?
C7 C8 1.388(3) . ?
C7 C6 1.529(3) . ?
C13 C14 1.396(2) . ?
C13 H13A 0.9300 . ?
O9 C16 1.369(2) . ?
O9 H9AA 0.8200 . ?
C17 C16 1.380(3) . ?
C17 H17A 0.94(3) . ?
C1 C2 1.363(3) . ?
C1 H1A 0.9300 . ?
C20 C21 1.380(3) . ?
C9 C8 1.383(3) . ?
C9 H9A 0.9300 . ?
C6 O2 1.407(2) . ?
C11 H11C 0.9300 . ?
C8 H8A 0.9300 . ?
C4 C3 1.385(4) . ?
C4 H4A 0.9300 . ?
C3 C2 1.359(4) . ?
C3 H3A 0.9300 . ?
C21 C22 1.267(6) . ?
C21 C22 1.579(5) 2_655 ?
C21 H21A 0.79(3) . ?
C2 H2A 0.9300 . ?
O10 O10 1.223(9) 2_655 ?
O10 C22 1.360(5) . ?
O10 C22 1.672(5) 2_655 ?
O10 H10A 0.8500 . ?
C22 C22 0.780(8) 2_655 ?
C22 C21 1.579(5) 2_655 ?
C22 O10 1.672(5) 2_655 ?
O2 H2B 0.8200 . ?
C14 C19 1.498(2) 7_566 ?
C19 C14 1.498(2) 7_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Cu1 O1 93.82(5) . . ?
O3 Cu1 O5 84.97(6) . . ?
O1 Cu1 O5 164.74(6) . . ?
O3 Cu1 N1 168.48(7) . . ?
O1 Cu1 N1 82.21(6) . . ?
O5 Cu1 N1 96.00(6) . . ?
O3 Cu1 O11 105.02(6) . . ?
O1 Cu1 O11 94.24(5) . . ?
O5 Cu1 O11 100.77(6) . . ?
N1 Cu1 O11 86.11(6) . . ?
O4 Cu2 O1 94.49(6) . . ?
O4 Cu2 O7 89.50(7) . . ?
O1 Cu2 O7 170.89(6) . . ?
O4 Cu2 N2 175.60(7) . . ?
O1 Cu2 N2 82.75(6) . . ?
O7 Cu2 N2 93.72(7) . . ?
C19 O3 Cu1 131.10(12) . . ?
C6 O1 Cu2 115.71(10) . . ?
C6 O1 Cu1 117.19(10) . . ?
Cu2 O1 Cu1 108.99(6) . . ?
C7 N2 C11 119.99(17) . . ?
C7 N2 Cu2 113.69(12) . . ?
C11 N2 Cu2 124.81(14) . . ?
C12 O5 Cu1 126.19(12) . . ?
C5 N1 C1 119.60(17) . . ?
C5 N1 Cu1 115.14(12) . . ?
C1 N1 Cu1 125.24(14) . . ?
C19 O4 Cu2 130.50(13) . . ?
C24 O7 Cu2 114.70(13) . . ?
O6 C12 O5 124.80(17) . . ?
O6 C12 C18 119.54(16) . . ?
O5 C12 C18 115.63(16) . . ?
C20 C23 C20 119.9(2) 2_655 . ?
C20 C23 H23A 120.03(12) 2_655 . ?
C20 C23 H23A 120.03(12) . . ?
C13 C18 C17 119.96(17) . . ?
C13 C18 C12 121.35(16) . . ?
C17 C18 C12 118.58(16) . . ?
C16 C15 C14 119.99(17) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
Cu1 O11 H11A 109.5 . . ?
Cu1 O11 H11B 116.8 . . ?
H11A O11 H11B 110.4 . . ?
O8 C24 O7 125.07(19) . . ?
O8 C24 C20 118.97(19) . . ?
O7 C24 C20 115.95(17) . . ?
C9 C10 C11 118.3(2) . . ?
C9 C10 H10D 120.9 . . ?
C11 C10 H10D 120.9 . . ?
N1 C5 C4 120.62(19) . . ?
N1 C5 C6 116.12(16) . . ?
C4 C5 C6 123.12(19) . . ?
N2 C7 C8 120.88(18) . . ?
N2 C7 C6 115.72(16) . . ?
C8 C7 C6 123.34(18) . . ?
C18 C13 C14 118.97(16) . . ?
C18 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C16 O9 H9AA 109.5 . . ?
C16 C17 C18 120.62(18) . . ?
C16 C17 H17A 119.9(15) . . ?
C18 C17 H17A 119.4(15) . . ?
O9 C16 C17 124.16(19) . . ?
O9 C16 C15 116.30(19) . . ?
C17 C16 C15 119.51(18) . . ?
N1 C1 C2 122.2(2) . . ?
N1 C1 H1A 118.9 . . ?
C2 C1 H1A 118.9 . . ?
C21 C20 C23 120.0(2) . . ?
C21 C20 C24 119.11(19) . . ?
C23 C20 C24 120.84(17) . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
O1 C6 O2 112.64(15) . . ?
O1 C6 C7 109.93(14) . . ?
O2 C6 C7 104.84(15) . . ?
O1 C6 C5 109.14(14) . . ?
O2 C6 C5 108.02(15) . . ?
C7 C6 C5 112.26(15) . . ?
N2 C11 C10 121.8(2) . . ?
N2 C11 H11C 119.1 . . ?
C10 C11 H11C 119.1 . . ?
C9 C8 C7 118.5(2) . . ?
C9 C8 H8A 120.7 . . ?
C7 C8 H8A 120.7 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C22 C21 C20 122.6(3) . . ?
C22 C21 C22 29.3(4) . 2_655 ?
C20 C21 C22 115.4(2) . 2_655 ?
C22 C21 H21A 114(2) . . ?
C20 C21 H21A 122(2) . . ?
C22 C21 H21A 121(2) 2_655 . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
O10 O10 C22 80.5(3) 2_655 . ?
O10 O10 C22 53.3(2) 2_655 2_655 ?
C22 O10 C22 27.4(3) . 2_655 ?
O10 O10 H10A 117.3 2_655 . ?
C22 O10 H10A 109.2 . . ?
C22 O10 H10A 122.2 2_655 . ?
C22 C22 C21 98.1(8) 2_655 . ?
C22 C22 O10 99.2(3) 2_655 . ?
C21 C22 O10 123.8(4) . . ?
C22 C22 C21 52.6(6) 2_655 2_655 ?
C21 C22 C21 114.2(3) . 2_655 ?
O10 C22 C21 118.7(3) . 2_655 ?
C22 C22 O10 53.4(2) 2_655 2_655 ?
C21 C22 O10 118.2(4) . 2_655 ?
O10 C22 O10 46.2(4) . 2_655 ?
C21 C22 O10 91.0(2) 2_655 2_655 ?
C6 O2 H2B 109.5 . . ?
C15 C14 C13 120.66(16) . . ?
C15 C14 C19 118.07(16) . 7_566 ?
C13 C14 C19 121.19(16) . 7_566 ?
O4 C19 O3 126.57(17) . . ?
O4 C19 C14 116.20(16) . 7_566 ?
O3 C19 C14 117.20(16) . 7_566 ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        28.73
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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 1555025'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H35 Cu4 N4 O23'
_chemical_formula_weight         1157.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.208(6)
_cell_length_b                   16.333(9)
_cell_length_c                   27.106(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.515(14)
_cell_angle_gamma                90
_cell_volume                     4505(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9854
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_F_000             2340
_exptl_transmission_factor_min   0.652
_exptl_transmission_factor_max   0.772
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.953
_shelx_estimated_absorpt_T_min   0.652
_shelx_estimated_absorpt_T_max   0.772
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_T_max  0.772
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   'Bruker SADABS'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex-II CCD'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43882
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.358
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8140
_reflns_number_gt                7411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0767P)²+16.3351P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8140
_refine_ls_number_parameters     613
_refine_ls_number_restraints     664
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1467
_refine_ls_wR_factor_gt          0.1447
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      11.404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6370(6) 0.7232(4) 0.4170(2) 0.0492(14) Uani 1 1 d . U . . .
H1 H 0.7164 0.7336 0.4351 0.059 Uiso 1 1 calc R U . . .
C2 C 0.5555(8) 0.6644(5) 0.4335(3) 0.072(2) Uani 1 1 d . U . . .
H2 H 0.5771 0.6363 0.4628 0.086 Uiso 1 1 calc R U . . .
C3 C 0.4398(8) 0.6480(5) 0.4049(3) 0.083(3) Uani 1 1 d . U . . .
H3 H 0.3833 0.6075 0.4147 0.099 Uiso 1 1 calc R U . . .
C4 C 0.4087(6) 0.6913(4) 0.3626(3) 0.0596(17) Uani 1 1 d . U . . .
H4 H 0.3308 0.6810 0.3434 0.072 Uiso 1 1 calc R U . . .
C5 C 0.4948(4) 0.7507(3) 0.34844(18) 0.0285(9) Uani 1 1 d . U . . .
C6 C 0.4748(4) 0.7991(3) 0.29966(16) 0.0240(8) Uani 1 1 d . U . . .
C7 C 0.3362(4) 0.8332(3) 0.29160(17) 0.0256(9) Uani 1 1 d . U . . .
C8 C 0.2289(5) 0.7875(3) 0.2737(2) 0.0388(12) Uani 1 1 d . U . . .
H8 H 0.2389 0.7340 0.2628 0.047 Uiso 1 1 calc R U . . .
C9 C 0.1061(5) 0.8237(3) 0.2724(3) 0.0505(15) Uani 1 1 d . U . . .
H9 H 0.0321 0.7957 0.2593 0.061 Uiso 1 1 calc R U . . .
C10 C 0.0949(5) 0.9019(3) 0.2910(3) 0.0547(17) Uani 1 1 d . U . . .
H10 H 0.0123 0.9251 0.2931 0.066 Uiso 1 1 calc R U . . .
C11 C 0.2062(5) 0.9454(3) 0.3062(2) 0.0447(14) Uani 1 1 d . U . . .
H11 H 0.1985 0.9988 0.3175 0.054 Uiso 1 1 calc R U . . .
C12 C 1.5299(6) 1.4626(3) 0.3269(2) 0.0438(13) Uani 1 1 d . U . . .
H12 H 1.4630 1.4971 0.3142 0.053 Uiso 1 1 calc R U . . .
C13 C 1.6535(6) 1.4930(4) 0.3345(3) 0.0619(18) Uani 1 1 d . U . . .
H13 H 1.6710 1.5480 0.3291 0.074 Uiso 1 1 calc R U . . .
C14 C 1.7521(8) 1.4398(5) 0.3506(3) 0.0673(17) Uani 1 1 d . U . . .
H14 H 1.8388 1.4579 0.3539 0.081 Uiso 1 1 calc R U . . .
C15 C 1.7234(6) 1.3593(4) 0.3619(3) 0.068(2) Uani 1 1 d . U . . .
H15 H 1.7893 1.3237 0.3741 0.082 Uiso 1 1 calc R U . . .
C16 C 1.5959(5) 1.3335(3) 0.35472(18) 0.0315(10) Uani 1 1 d . U . . .
C17 C 1.5555(4) 1.2440(3) 0.36228(16) 0.0258(9) Uani 1 1 d . U . . .
C18 C 1.5936(4) 1.2103(3) 0.41386(17) 0.0283(9) Uani 1 1 d . U . . .
C19 C 1.7220(5) 1.1929(4) 0.4308(2) 0.0476(14) Uani 1 1 d . U . . .
H19 H 1.7907 1.2036 0.4112 0.057 Uiso 1 1 calc R U . . .
C20 C 1.7463(6) 1.1590(4) 0.4780(3) 0.0596(17) Uani 1 1 d . U . . .
H20 H 1.8320 1.1474 0.4902 0.071 Uiso 1 1 calc R U . . .
C21 C 1.6448(6) 1.1429(4) 0.5057(2) 0.0565(16) Uani 1 1 d . U . . .
H21 H 1.6593 1.1207 0.5373 0.068 Uiso 1 1 calc R U . . .
C22 C 1.5201(5) 1.1603(4) 0.4862(2) 0.0433(12) Uani 1 1 d . U . . .
H22 H 1.4500 1.1486 0.5050 0.052 Uiso 1 1 calc R U . . .
C23 C 0.8661(4) 1.0526(2) 0.26914(15) 0.0208(8) Uani 1 1 d . U . . .
C24 C 0.8876(4) 1.0464(3) 0.21882(17) 0.0253(9) Uani 1 1 d . U . . .
C25 C 0.9859(4) 1.0939(3) 0.20079(16) 0.0263(9) Uani 1 1 d . U . . .
H25 H 0.9986 1.0914 0.1672 0.032 Uiso 1 1 calc R U . . .
C26 C 1.0658(4) 1.1450(2) 0.23093(16) 0.0218(8) Uani 1 1 d . U . . .
C27 C 1.0469(4) 1.1487(2) 0.28150(16) 0.0207(8) Uani 1 1 d . U . . .
C28 C 0.9471(4) 1.1030(3) 0.29971(16) 0.0229(8) Uani 1 1 d . U . . .
H28 H 0.9338 1.1060 0.3332 0.027 Uiso 1 1 calc R U . . .
C29 C 0.7619(4) 1.0028(3) 0.29218(16) 0.0225(8) Uani 1 1 d . U . . .
C30 C 1.1374(4) 1.1996(3) 0.31575(15) 0.0219(8) Uani 1 1 d . U . . .
C31 C 0.8155(5) 0.9842(3) 0.18536(18) 0.0389(12) Uani 1 1 d . U . . .
C32 C 1.1766(4) 1.1913(3) 0.20942(16) 0.0236(8) Uani 1 1 d . U . . .
C33 C 1.0150(4) 0.9855(3) 0.45037(16) 0.0256(9) Uani 1 1 d . U . . .
H33 H 1.0257 0.9758 0.4171 0.031 Uiso 1 1 calc R U . . .
C34 C 0.9093(4) 0.9513(3) 0.47177(15) 0.0232(8) Uani 1 1 d . U . . .
C35 C 0.8944(4) 0.9657(3) 0.52209(15) 0.0235(8) Uani 1 1 d . U . . .
C36 C 0.8058(4) 0.9092(3) 0.43893(15) 0.0247(9) Uani 1 1 d . U . . .
C37 C 0.7875(4) 0.9262(3) 0.54867(15) 0.0260(9) Uani 1 1 d . U . . .
N1 N 0.6060(4) 0.7664(2) 0.37548(14) 0.0287(8) Uani 1 1 d . U . . .
N2 N 0.3256(3) 0.9119(2) 0.30500(16) 0.0297(8) Uani 1 1 d . U . . .
N3 N 1.5003(4) 1.3841(2) 0.33698(15) 0.0300(8) Uani 1 1 d . U . . .
N4 N 1.4944(4) 1.1934(2) 0.44111(14) 0.0284(8) Uani 1 1 d . U . . .
O1 O 0.5653(3) 0.86316(17) 0.30022(11) 0.0221(6) Uani 1 1 d . U . . .
O2 O 0.4918(3) 0.7448(2) 0.26036(12) 0.0324(7) Uani 1 1 d . U . . .
H2A H 0.5659 0.7251 0.2636 0.049 Uiso 1 1 calc R U . . .
O3 O 1.4196(3) 1.23636(18) 0.35125(11) 0.0254(6) Uani 1 1 d . U . . .
O4 O 1.6231(3) 1.1939(2) 0.33048(13) 0.0381(8) Uani 1 1 d . U . . .
H4A H 1.6072 1.2092 0.3018 0.057 Uiso 1 1 calc R U . . .
O5 O 0.6453(3) 1.02560(18) 0.28227(13) 0.0287(7) Uani 1 1 d . U . . .
O6 O 0.8028(3) 0.9471(2) 0.32067(12) 0.0320(7) Uani 1 1 d . U . . .
O7 O 1.1793(3) 1.26512(18) 0.29825(12) 0.0290(7) Uani 1 1 d . U . . .
O8 O 1.1647(3) 1.1723(2) 0.35844(12) 0.0349(8) Uani 1 1 d . U . . .
O9 O 0.8099(6) 0.9947(4) 0.1401(2) 0.0900(16) Uani 1 1 d . U . . .
O10 O 0.7604(3) 0.92747(19) 0.20615(12) 0.0321(7) Uani 1 1 d . U . . .
O11 O 1.1487(3) 1.2497(2) 0.18135(13) 0.0342(7) Uani 1 1 d . U . . .
O12 O 1.2899(3) 1.16322(19) 0.22127(13) 0.0308(7) Uani 1 1 d D U . . .
O13 O 0.5134(4) 1.0074(3) 0.38406(13) 0.0439(9) Uani 1 1 d . U . . .
H13A H 0.5843 1.0392 0.3962 0.066 Uiso 1 1 calc R U . . .
H13B H 0.4515 0.9901 0.4052 0.066 Uiso 1 1 calc DR U . . .
O14 O 0.3973(3) 1.07976(18) 0.29780(13) 0.0314(7) Uani 1 1 d . U . . .
H14A H 0.4401 1.1255 0.2864 0.047 Uiso 1 1 calc R U . . .
H14B H 0.3105 1.0838 0.3056 0.047 Uiso 1 1 calc R U . . .
O15 O 0.8456(3) 0.8624(2) 0.40549(11) 0.0295(7) Uani 1 1 d . U . . .
O16 O 0.6900(3) 0.9247(2) 0.44404(12) 0.0365(8) Uani 1 1 d . U . . .
O17 O 0.7769(3) 0.8479(2) 0.54369(11) 0.0308(7) Uani 1 1 d . U . . .
O18 O 0.7236(3) 0.9685(2) 0.57523(13) 0.0392(8) Uani 1 1 d . U . . .
O19 O 1.2583(5) 1.3431(3) 0.4114(2) 0.0792(15) Uani 1 1 d D U . . .
H19A H 1.2063 1.3337 0.4264 0.119 Uiso 1 1 d DR U . . .
H19B H 1.2941 1.3641 0.4279 0.119 Uiso 1 1 d R U . . .
Cu1 Cu 0.49188(5) 0.97310(3) 0.30551(2) 0.02250(15) Uani 1 1 d . U . . .
Cu2 Cu 0.71755(5) 0.85116(3) 0.34788(2) 0.02247(14) Uani 1 1 d . U . . .
Cu3 Cu 1.32730(5) 1.33208(3) 0.32298(2) 0.02630(15) Uani 1 1 d . U . . .
Cu4 Cu 1.31992(5) 1.19585(3) 0.40409(2) 0.02575(15) Uani 1 1 d . U . . .
O20 O 1.0712(8) 0.7620(6) 0.3981(4) 0.146(3) Uani 1 1 d . . . . .
O30 O 2.0286(14) 1.2831(9) 0.4544(6) 0.219(6) Uani 1 1 d . U . . .
O40 O 0.5450(14) 0.5534(9) 0.5454(5) 0.216(5) Uani 1 1 d . U . . .
O50 O 0.899(3) 1.1143(19) 0.0600(11) 0.429(15) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.344(7) . ?
C1 C2 1.368(8) . ?
C2 C3 1.386(11) . ?
C3 C4 1.365(10) . ?
C4 C5 1.384(7) . ?
C5 N1 1.326(6) . ?
C5 C6 1.540(6) . ?
C6 O1 1.396(5) . ?
C6 O2 1.407(5) . ?
C6 C7 1.519(6) . ?
C7 N2 1.342(6) . ?
C7 C8 1.381(6) . ?
C8 C9 1.384(7) . ?
C9 C10 1.380(8) . ?
C10 C11 1.377(8) . ?
C11 N2 1.339(6) . ?
C12 N3 1.350(6) . ?
C12 C13 1.357(8) . ?
C13 C14 1.374(10) . ?
C14 C15 1.387(10) . ?
C15 C16 1.368(7) . ?
C16 N3 1.339(6) . ?
C16 C17 1.538(6) . ?
C17 O3 1.401(5) . ?
C17 O4 1.408(6) . ?
C17 C18 1.524(6) . ?
C18 N4 1.329(6) . ?
C18 C19 1.383(7) . ?
C19 C20 1.398(8) . ?
C20 C21 1.354(9) . ?
C21 C22 1.369(8) . ?
C22 N4 1.344(6) . ?
C23 C28 1.392(6) . ?
C23 C24 1.402(6) . ?
C23 C29 1.513(5) . ?
C24 C25 1.387(6) . ?
C24 C31 1.514(6) . ?
C25 C26 1.387(6) . ?
C26 C27 1.401(6) . ?
C26 C32 1.515(5) . ?
C27 C28 1.385(6) . ?
C27 C30 1.507(6) . ?
C29 O6 1.245(5) . ?
C29 O5 1.256(5) . ?
C30 O8 1.252(5) . ?
C30 O7 1.258(5) . ?
C31 O9 1.236(8) . ?
C31 O10 1.242(6) . ?
C32 O11 1.239(5) . ?
C32 O12 1.263(5) . ?
C33 C34 1.383(6) . ?
C33 C35 1.393(6) 3_776 ?
C34 C35 1.404(6) . ?
C34 C36 1.495(6) . ?
C35 C33 1.393(6) 3_776 ?
C35 C37 1.499(6) . ?
C36 O16 1.227(5) . ?
C36 O15 1.277(5) . ?
C37 O18 1.223(6) . ?
C37 O17 1.290(6) . ?
N1 Cu2 1.977(4) . ?
N2 Cu1 1.969(4) . ?
N3 Cu3 1.969(4) . ?
N4 Cu4 1.975(4) . ?
O1 Cu2 1.951(3) . ?
O1 Cu1 1.956(3) . ?
O3 Cu4 1.938(3) . ?
O3 Cu3 1.951(3) . ?
O5 Cu1 1.934(3) . ?
O6 Cu2 1.964(3) . ?
O7 Cu3 1.941(3) . ?
O8 Cu4 1.970(3) . ?
O10 Cu3 1.934(3) 2_745 ?
O11 Cu2 2.325(3) 2_755 ?
O13 Cu1 2.196(4) . ?
O14 Cu1 1.995(3) . ?
O15 Cu2 1.965(3) . ?
O17 Cu4 1.926(3) 3_776 ?
Cu2 O11 2.326(3) 2_745 ?
Cu3 O10 1.934(3) 2_755 ?
Cu4 O17 1.926(3) 3_776 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.2(6) . . ?
C1 C2 C3 117.8(6) . . ?
C4 C3 C2 120.1(6) . . ?
C3 C4 C5 119.1(6) . . ?
N1 C5 C4 121.1(5) . . ?
N1 C5 C6 115.2(4) . . ?
C4 C5 C6 123.5(5) . . ?
O1 C6 O2 111.1(3) . . ?
O1 C6 C7 109.6(3) . . ?
O2 C6 C7 106.9(3) . . ?
O1 C6 C5 109.4(3) . . ?
O2 C6 C5 108.1(3) . . ?
C7 C6 C5 111.8(3) . . ?
N2 C7 C8 122.2(4) . . ?
N2 C7 C6 114.0(4) . . ?
C8 C7 C6 123.8(4) . . ?
C7 C8 C9 118.1(5) . . ?
C10 C9 C8 119.1(5) . . ?
C11 C10 C9 119.8(5) . . ?
N2 C11 C10 120.9(5) . . ?
N3 C12 C13 122.5(5) . . ?
C12 C13 C14 117.8(6) . . ?
C13 C14 C15 120.5(7) . . ?
C16 C15 C14 118.4(6) . . ?
N3 C16 C15 121.3(5) . . ?
N3 C16 C17 116.0(4) . . ?
C15 C16 C17 122.4(5) . . ?
O3 C17 O4 110.1(4) . . ?
O3 C17 C18 109.9(3) . . ?
O4 C17 C18 104.5(4) . . ?
O3 C17 C16 109.1(3) . . ?
O4 C17 C16 108.7(4) . . ?
C18 C17 C16 114.4(4) . . ?
N4 C18 C19 121.1(4) . . ?
N4 C18 C17 115.7(4) . . ?
C19 C18 C17 123.0(4) . . ?
C18 C19 C20 118.7(5) . . ?
C21 C20 C19 119.8(5) . . ?
C20 C21 C22 118.3(5) . . ?
N4 C22 C21 123.0(5) . . ?
C28 C23 C24 119.4(4) . . ?
C28 C23 C29 118.4(4) . . ?
C24 C23 C29 122.1(4) . . ?
C25 C24 C23 118.4(4) . . ?
C25 C24 C31 119.7(4) . . ?
C23 C24 C31 121.7(4) . . ?
C26 C25 C24 122.5(4) . . ?
C25 C26 C27 118.8(4) . . ?
C25 C26 C32 119.8(4) . . ?
C27 C26 C32 121.3(4) . . ?
C28 C27 C26 119.2(4) . . ?
C28 C27 C30 120.7(4) . . ?
C26 C27 C30 120.1(4) . . ?
C27 C28 C23 121.7(4) . . ?
O6 C29 O5 128.0(4) . . ?
O6 C29 C23 115.9(4) . . ?
O5 C29 C23 116.0(4) . . ?
O8 C30 O7 126.5(4) . . ?
O8 C30 C27 117.0(4) . . ?
O7 C30 C27 116.6(4) . . ?
O9 C31 O10 124.5(5) . . ?
O9 C31 C24 119.0(5) . . ?
O10 C31 C24 116.4(4) . . ?
O11 C32 O12 126.7(4) . . ?
O11 C32 C26 118.6(4) . . ?
O12 C32 C26 114.7(4) . . ?
C34 C33 C35 120.9(4) . 3_776 ?
C33 C34 C35 119.2(4) . . ?
C33 C34 C36 118.3(4) . . ?
C35 C34 C36 122.0(4) . . ?
C33 C35 C34 119.9(4) 3_776 . ?
C33 C35 C37 117.8(4) 3_776 . ?
C34 C35 C37 122.3(4) . . ?
O16 C36 O15 124.5(4) . . ?
O16 C36 C34 118.7(4) . . ?
O15 C36 C34 116.7(4) . . ?
O18 C37 O17 125.3(4) . . ?
O18 C37 C35 118.8(4) . . ?
O17 C37 C35 115.7(4) . . ?
C5 N1 C1 119.7(4) . . ?
C5 N1 Cu2 114.8(3) . . ?
C1 N1 Cu2 125.5(4) . . ?
C11 N2 C7 119.4(4) . . ?
C11 N2 Cu1 125.3(3) . . ?
C7 N2 Cu1 113.6(3) . . ?
C16 N3 C12 119.4(4) . . ?
C16 N3 Cu3 114.9(3) . . ?
C12 N3 Cu3 125.6(4) . . ?
C18 N4 C22 119.1(4) . . ?
C18 N4 Cu4 114.2(3) . . ?
C22 N4 Cu4 125.0(3) . . ?
C6 O1 Cu2 115.1(3) . . ?
C6 O1 Cu1 115.6(2) . . ?
Cu2 O1 Cu1 109.49(14) . . ?
C17 O3 Cu4 116.2(3) . . ?
C17 O3 Cu3 116.9(2) . . ?
Cu4 O3 Cu3 107.35(15) . . ?
C29 O5 Cu1 125.2(3) . . ?
C29 O6 Cu2 132.8(3) . . ?
C30 O7 Cu3 128.8(3) . . ?
C30 O8 Cu4 128.4(3) . . ?
C31 O10 Cu3 128.8(3) . 2_745 ?
C32 O11 Cu2 130.2(3) . 2_755 ?
C36 O15 Cu2 113.0(3) . . ?
C37 O17 Cu4 109.5(3) . 3_776 ?
O5 Cu1 O1 93.34(12) . . ?
O5 Cu1 N2 160.49(16) . . ?
O1 Cu1 N2 82.43(14) . . ?
O5 Cu1 O14 88.64(13) . . ?
O1 Cu1 O14 168.38(13) . . ?
N2 Cu1 O14 91.91(15) . . ?
O5 Cu1 O13 100.42(15) . . ?
O1 Cu1 O13 107.21(14) . . ?
N2 Cu1 O13 99.01(16) . . ?
O14 Cu1 O13 83.65(14) . . ?
O1 Cu2 O6 91.42(13) . . ?
O1 Cu2 O15 164.25(13) . . ?
O6 Cu2 O15 86.39(14) . . ?
O1 Cu2 N1 82.45(14) . . ?
O6 Cu2 N1 170.56(15) . . ?
O15 Cu2 N1 97.57(15) . . ?
O1 Cu2 O11 107.73(12) . 2_745 ?
O6 Cu2 O11 98.67(14) . 2_745 ?
O15 Cu2 O11 88.02(13) . 2_745 ?
N1 Cu2 O11 90.06(15) . 2_745 ?
O10 Cu3 O7 89.44(14) 2_755 . ?
O10 Cu3 O3 178.47(14) 2_755 . ?
O7 Cu3 O3 91.33(13) . . ?
O10 Cu3 N3 96.34(16) 2_755 . ?
O7 Cu3 N3 166.22(16) . . ?
O3 Cu3 N3 82.62(15) . . ?
O17 Cu4 O3 178.17(14) 3_776 . ?
O17 Cu4 O8 87.44(14) 3_776 . ?
O3 Cu4 O8 92.64(13) . . ?
O17 Cu4 N4 96.51(15) 3_776 . ?
O3 Cu4 N4 82.94(14) . . ?
O8 Cu4 N4 164.57(16) . . ?

_refine_diff_density_max         2.126
_refine_diff_density_min         -0.925
_refine_diff_density_rms         0.126

####################################################################### 
# 
# 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 1555023'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 Cu2 N2 O9'
_chemical_formula_weight         592.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   23.809(3)
_cell_length_b                   11.5102(12)
_cell_length_c                   18.1434(19)
_cell_angle_alpha                90
_cell_angle_beta                 119.9250(10)
_cell_angle_gamma                90
_cell_volume                     4309.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.03

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_F_000             2392
_exptl_transmission_factor_min   0.544
_exptl_transmission_factor_max   0.723
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    2.036
_shelx_estimated_absorpt_T_min   0.544
_shelx_estimated_absorpt_T_max   0.723
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_T_max  0.723
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   'Bruker SADABS'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex-II CCD'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21675
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.591
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3893
_reflns_number_gt                3583
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+5.1683P] 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         3893
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0629
_refine_ls_goodness_of_fit_ref   1.062
_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
Cu1 Cu 0.19704(2) 0.31710(2) 0.25387(2) 0.02372(8) Uani 1 1 d . . . . .
Cu2 Cu 0.31712(2) 0.37228(2) 0.22759(2) 0.02534(8) Uani 1 1 d . . . . .
O1 O 0.23088(6) 0.42563(12) 0.20231(8) 0.0232(3) Uani 1 1 d . . . . .
O2 O 0.17562(8) 0.57833(13) 0.11039(10) 0.0388(4) Uani 1 1 d . . . . .
H2A H 0.1585 0.5960 0.1385 0.058 Uiso 1 1 calc R U . . .
O3 O 0.27057(7) 0.33745(14) 0.36630(9) 0.0328(3) Uani 1 1 d . . . . .
O4 O 0.35510(7) 0.37927(15) 0.34947(9) 0.0371(4) Uani 1 1 d . . . . .
O5 O 0.15478(7) 0.24923(13) 0.31247(9) 0.0307(3) Uani 1 1 d . . . . .
O6 O 0.14594(8) 0.06721(13) 0.26573(10) 0.0344(4) Uani 1 1 d . . . . .
O7 O 0.39304(7) 0.28951(14) 0.24053(10) 0.0348(4) Uani 1 1 d . . . . .
O8 O 0.35708(8) 0.12516(15) 0.26644(11) 0.0416(4) Uani 1 1 d . . . . .
O9 O 0.22102(11) 0.15722(16) 0.20042(12) 0.0368(4) Uani 1 1 d . . . . .
N1 N 0.11822(8) 0.32763(15) 0.14046(11) 0.0289(4) Uani 1 1 d . . . . .
N2 N 0.27568(9) 0.37698(15) 0.10235(11) 0.0267(4) Uani 1 1 d . . . . .
C1 C 0.06194(11) 0.2727(2) 0.11676(16) 0.0439(6) Uani 1 1 d . . . . .
H1 H 0.0583 0.2267 0.1563 0.053 Uiso 1 1 calc R U . . .
C2 C 0.01013(13) 0.2823(3) 0.03689(18) 0.0614(9) Uani 1 1 d . . . . .
H2 H -0.0281 0.2422 0.0215 0.074 Uiso 1 1 calc R U . . .
C3 C 0.01550(15) 0.3518(4) -0.01985(19) 0.0866(14) Uani 1 1 d . . . . .
H3 H -0.0197 0.3616 -0.0743 0.104 Uiso 1 1 calc R U . . .
C4 C 0.07289(14) 0.4073(4) 0.00343(18) 0.0752(12) Uani 1 1 d . . . . .
H4 H 0.0771 0.4539 -0.0354 0.090 Uiso 1 1 calc R U . . .
C5 C 0.12429(10) 0.3935(2) 0.08487(14) 0.0322(5) Uani 1 1 d . . . . .
C6 C 0.18897(10) 0.45836(18) 0.11862(12) 0.0255(4) Uani 1 1 d . . . . .
C7 C 0.22029(10) 0.43639(19) 0.06414(13) 0.0278(4) Uani 1 1 d . . . . .
C8 C 0.19530(12) 0.4772(2) -0.01777(14) 0.0394(6) Uani 1 1 d . . . . .
H8 H 0.1585 0.5238 -0.0422 0.047 Uiso 1 1 calc R U . . .
C9 C 0.22571(13) 0.4477(2) -0.06295(15) 0.0438(6) Uani 1 1 d . . . . .
H9 H 0.2088 0.4724 -0.1189 0.053 Uiso 1 1 calc R U . . .
C10 C 0.28095(13) 0.3817(2) -0.02494(15) 0.0408(6) Uani 1 1 d . . . . .
H10 H 0.3012 0.3589 -0.0551 0.049 Uiso 1 1 calc R U . . .
C11 C 0.30579(12) 0.3501(2) 0.05844(15) 0.0338(5) Uani 1 1 d . . . . .
H11 H 0.3445 0.3090 0.0855 0.041 Uiso 1 1 calc R U . . .
C12 C 0.12112(10) 0.10503(18) 0.37459(13) 0.0248(4) Uani 1 1 d . . . . .
C13 C 0.07211(10) 0.0231(2) 0.34897(13) 0.0328(5) Uani 1 1 d . . . . .
H13 H 0.0535 -0.0082 0.2945 0.039 Uiso 1 1 calc R U . . .
C14 C 0.05065(11) -0.0126(2) 0.40339(15) 0.0370(5) Uani 1 1 d . . . . .
H14 H 0.0156 -0.0629 0.3842 0.044 Uiso 1 1 calc R U . . .
C15 C 0.08144(10) 0.0268(2) 0.48632(14) 0.0318(5) Uani 1 1 d . . . . .
H15 H 0.0675 0.0020 0.5233 0.038 Uiso 1 1 calc R U . . .
C16 C 0.13326(10) 0.10344(17) 0.51455(13) 0.0244(4) Uani 1 1 d . . . . .
C17 C 0.15180(10) 0.14560(17) 0.45784(12) 0.0238(4) Uani 1 1 d . . . . .
H17 H 0.1846 0.2007 0.4756 0.029 Uiso 1 1 calc R U . . .
C18 C 0.14279(9) 0.14164(18) 0.31293(12) 0.0256(4) Uani 1 1 d . . . . .
C19 C 0.32776(10) 0.36765(17) 0.39281(13) 0.0247(4) Uani 1 1 d . . . . .
C20 C 0.44998(10) 0.11800(18) 0.25168(14) 0.0271(4) Uani 1 1 d . . . . .
C21 C 0.45035(12) -0.0023(2) 0.25126(19) 0.0456(6) Uani 1 1 d . . . . .
H21 H 0.4169 -0.0431 0.2518 0.055 Uiso 1 1 calc R U . . .
C22 C 0.5000 -0.0616(3) 0.2500 0.0614(12) Uani 1 2 d S T P . .
H22 H 0.5000 -0.1424 0.2500 0.074 Uiso 1 2 calc R U P . .
C23 C 0.5000 0.1774(3) 0.2500 0.0253(6) Uani 1 2 d S T P . .
H23 H 0.5000 0.2582 0.2500 0.030 Uiso 1 2 calc R U P . .
C24 C 0.39567(10) 0.1814(2) 0.25344(13) 0.0282(5) Uani 1 1 d . . . . .
H9A H 0.2531(16) 0.137(3) 0.220(2) 0.044(10) Uiso 1 1 d . . . . .
H9B H 0.2019(18) 0.107(3) 0.212(2) 0.068(11) Uiso 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
Cu1 O3 1.9281(15) . ?
Cu1 O5 1.9548(14) . ?
Cu1 O1 1.9588(13) . ?
Cu1 N1 1.9793(17) . ?
Cu1 O9 2.2815(18) . ?
Cu2 O4 1.9285(15) . ?
Cu2 O7 1.9512(15) . ?
Cu2 O1 1.9655(13) . ?
Cu2 N2 1.9756(17) . ?
Cu2 O6 2.3909(16) 4 ?
O1 C6 1.390(2) . ?
O2 C6 1.408(3) . ?
O3 C19 1.246(3) . ?
O4 C19 1.253(3) . ?
O5 C18 1.272(3) . ?
O6 C18 1.240(3) . ?
O6 Cu2 2.3909(16) 4_545 ?
O7 C24 1.262(3) . ?
O8 C24 1.239(3) . ?
N1 C5 1.326(3) . ?
N1 C1 1.344(3) . ?
N2 C7 1.332(3) . ?
N2 C11 1.347(3) . ?
C1 C2 1.360(4) . ?
C2 C3 1.359(4) . ?
C3 C4 1.371(4) . ?
C4 C5 1.379(4) . ?
C5 C6 1.537(3) . ?
C6 C7 1.527(3) . ?
C7 C8 1.379(3) . ?
C8 C9 1.380(4) . ?
C9 C10 1.370(4) . ?
C10 C11 1.370(3) . ?
C12 C13 1.388(3) . ?
C12 C17 1.390(3) . ?
C12 C18 1.507(3) . ?
C13 C14 1.381(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.390(3) . ?
C16 C17 1.394(3) . ?
C16 C19 1.497(3) 7_556 ?
C19 C16 1.497(3) 7_556 ?
C20 C21 1.385(3) . ?
C20 C23 1.387(2) . ?
C20 C24 1.499(3) . ?
C21 C22 1.375(3) . ?
C22 C21 1.375(3) 2_655 ?
C23 C20 1.387(2) 2_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Cu1 O5 85.13(6) . . ?
O3 Cu1 O1 93.16(6) . . ?
O5 Cu1 O1 163.88(6) . . ?
O3 Cu1 N1 169.10(7) . . ?
O5 Cu1 N1 96.40(7) . . ?
O1 Cu1 N1 82.36(6) . . ?
O3 Cu1 O9 105.08(7) . . ?
O5 Cu1 O9 102.40(7) . . ?
O1 Cu1 O9 93.54(6) . . ?
N1 Cu1 O9 85.18(8) . . ?
O4 Cu2 O7 90.35(7) . . ?
O4 Cu2 O1 95.29(6) . . ?
O7 Cu2 O1 167.91(6) . . ?
O4 Cu2 N2 175.71(7) . . ?
O7 Cu2 N2 93.03(7) . . ?
O1 Cu2 N2 81.89(6) . . ?
O4 Cu2 O6 87.28(6) . 4 ?
O7 Cu2 O6 99.02(6) . 4 ?
O1 Cu2 O6 91.93(6) . 4 ?
N2 Cu2 O6 89.58(6) . 4 ?
C6 O1 Cu1 116.90(12) . . ?
C6 O1 Cu2 115.91(11) . . ?
Cu1 O1 Cu2 108.66(6) . . ?
C19 O3 Cu1 133.06(13) . . ?
C19 O4 Cu2 128.45(14) . . ?
C18 O5 Cu1 124.81(13) . . ?
C18 O6 Cu2 139.54(13) . 4_545 ?
C24 O7 Cu2 117.45(14) . . ?
C5 N1 C1 119.68(19) . . ?
C5 N1 Cu1 114.79(14) . . ?
C1 N1 Cu1 125.51(15) . . ?
C7 N2 C11 119.39(19) . . ?
C7 N2 Cu2 114.15(13) . . ?
C11 N2 Cu2 124.50(16) . . ?
N1 C1 C2 122.2(2) . . ?
C3 C2 C1 118.5(3) . . ?
C2 C3 C4 119.8(3) . . ?
C3 C4 C5 119.5(3) . . ?
N1 C5 C4 120.4(2) . . ?
N1 C5 C6 116.25(18) . . ?
C4 C5 C6 123.2(2) . . ?
O1 C6 O2 112.51(17) . . ?
O1 C6 C7 110.23(16) . . ?
O2 C6 C7 104.54(16) . . ?
O1 C6 C5 109.52(16) . . ?
O2 C6 C5 107.82(17) . . ?
C7 C6 C5 112.16(17) . . ?
N2 C7 C8 121.2(2) . . ?
N2 C7 C6 115.12(17) . . ?
C8 C7 C6 123.6(2) . . ?
C7 C8 C9 119.0(2) . . ?
C10 C9 C8 119.6(2) . . ?
C9 C10 C11 118.7(2) . . ?
N2 C11 C10 121.9(2) . . ?
C13 C12 C17 119.37(19) . . ?
C13 C12 C18 118.91(18) . . ?
C17 C12 C18 121.59(18) . . ?
C14 C13 C12 120.8(2) . . ?
C13 C14 C15 119.8(2) . . ?
C14 C15 C16 120.06(19) . . ?
C15 C16 C17 119.92(19) . . ?
C15 C16 C19 119.61(18) . 7_556 ?
C17 C16 C19 120.28(18) . 7_556 ?
C12 C17 C16 119.80(19) . . ?
O6 C18 O5 125.25(19) . . ?
O6 C18 C12 118.73(19) . . ?
O5 C18 C12 115.99(18) . . ?
O3 C19 O4 126.66(19) . . ?
O3 C19 C16 116.20(17) . 7_556 ?
O4 C19 C16 117.10(18) . 7_556 ?
C21 C20 C23 119.0(2) . . ?
C21 C20 C24 119.65(19) . . ?
C23 C20 C24 121.3(2) . . ?
C22 C21 C20 120.3(2) . . ?
C21 C22 C21 120.4(3) 2_655 . ?
C20 C23 C20 120.9(3) . 2_655 ?
O8 C24 O7 125.3(2) . . ?
O8 C24 C20 118.6(2) . . ?
O7 C24 C20 116.07(18) . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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 1555024'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Cu0.50 N2 O7'
_chemical_formula_weight         417.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.744(17)
_cell_length_b                   7.959(10)
_cell_length_c                   16.19(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.942(15)
_cell_angle_gamma                90
_cell_volume                     1764(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3192
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      22.53

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_F_000             862
_exptl_transmission_factor_min   0.802
_exptl_transmission_factor_max   0.850
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.700
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.850
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   'Bruker SADABS'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex-II CCD'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11927
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.526
_diffrn_reflns_theta_max         24.886
_diffrn_reflns_theta_full        24.886
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2992
_reflns_number_gt                2004
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0683P)²+12.5476P] 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         2992
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1877
_refine_ls_wR_factor_gt          0.1581
_refine_ls_goodness_of_fit_ref   0.837
_refine_ls_restrained_S_all      0.837
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.0000 0.5000 0.0391(3) Uani 1 2 d S . P . .
O1 O 0.0936(3) 0.0124(4) 0.3766(2) 0.0398(9) Uani 1 1 d . . . . .
H1A H 0.1534 0.0126 0.3832 0.060 Uiso 1 1 calc R U . . .
O2 O 0.0904(3) -0.1993(5) 0.2741(2) 0.0548(11) Uani 1 1 d . . . . .
H2A H 0.1501 -0.2068 0.2777 0.082 Uiso 1 1 calc R U . . .
O3 O 0.2761(3) 0.0890(6) 0.4228(2) 0.0540(11) Uani 1 1 d . . . . .
O4 O 0.3690(4) 0.0393(5) 0.3198(2) 0.0560(12) Uani 1 1 d . . . . .
O5 O 0.4184(4) 0.3619(6) 0.6756(3) 0.0678(14) Uani 1 1 d . . . . .
H5A H 0.4183 0.3990 0.7229 0.102 Uiso 1 1 calc R U . . .
O6 O 0.5734(4) 0.4380(6) 0.6929(3) 0.0633(12) Uani 1 1 d . . . . .
O7 O 0.7286(4) 0.2202(8) 0.7476(4) 0.0709(15) Uani 1 1 d . . . . .
N1 N 0.0666(4) -0.2271(5) 0.4960(3) 0.0407(11) Uani 1 1 d . . . . .
N2 N -0.0892(4) -0.0706(5) 0.4044(3) 0.0384(11) Uani 1 1 d . . . . .
C1 C 0.0890(5) -0.3270(7) 0.5612(4) 0.0466(15) Uani 1 1 d . . . . .
H1 H 0.0722 -0.2931 0.6131 0.056 Uiso 1 1 calc R U . . .
C2 C 0.1365(5) -0.4799(7) 0.5541(4) 0.0563(17) Uani 1 1 d . . . . .
H2 H 0.1522 -0.5468 0.6005 0.068 Uiso 1 1 calc R U . . .
C3 C 0.1600(5) -0.5304(7) 0.4760(4) 0.0582(18) Uani 1 1 d . . . . .
H3 H 0.1914 -0.6324 0.4694 0.070 Uiso 1 1 calc R U . . .
C4 C 0.1366(5) -0.4286(7) 0.4088(4) 0.0496(15) Uani 1 1 d . . . . .
H4 H 0.1515 -0.4617 0.3562 0.059 Uiso 1 1 calc R U . . .
C5 C 0.0902(4) -0.2757(6) 0.4197(3) 0.0401(13) Uani 1 1 d . . . . .
C6 C 0.0600(4) -0.1512(7) 0.3502(3) 0.0407(13) Uani 1 1 d . . . . .
C7 C -0.0492(5) -0.1400(6) 0.3399(3) 0.0413(14) Uani 1 1 d . . . . .
C8 C -0.1038(5) -0.2018(7) 0.2715(3) 0.0442(14) Uani 1 1 d . . . . .
H8 H -0.0741 -0.2552 0.2292 0.053 Uiso 1 1 calc R U . . .
C9 C -0.2033(5) -0.1829(8) 0.2671(4) 0.0534(16) Uani 1 1 d . . . . .
H9 H -0.2418 -0.2215 0.2209 0.064 Uiso 1 1 calc R U . . .
C10 C -0.2468(5) -0.1057(7) 0.3319(4) 0.0487(15) Uani 1 1 d . . . . .
H10 H -0.3140 -0.0904 0.3294 0.058 Uiso 1 1 calc R U . . .
C11 C -0.1867(5) -0.0521(7) 0.4003(4) 0.0449(14) Uani 1 1 d . . . . .
H11 H -0.2147 -0.0022 0.4444 0.054 Uiso 1 1 calc R U . . .
C12 C 0.4412(5) 0.1772(7) 0.4397(3) 0.0430(14) Uani 1 1 d . . . . .
C13 C 0.4332(5) 0.2384(7) 0.5196(3) 0.0445(14) Uani 1 1 d . . . . .
H13 H 0.3740 0.2298 0.5430 0.053 Uiso 1 1 calc R U . . .
C14 C 0.5121(5) 0.3116(7) 0.5644(3) 0.0428(14) Uani 1 1 d . . . . .
C15 C 0.6015(5) 0.3245(8) 0.5300(4) 0.0528(16) Uani 1 1 d . . . . .
H15 H 0.6553 0.3716 0.5603 0.063 Uiso 1 1 calc R U . . .
C16 C 0.6092(5) 0.2659(8) 0.4499(4) 0.0550(16) Uani 1 1 d . . . . .
H16 H 0.6681 0.2768 0.4261 0.066 Uiso 1 1 calc R U . . .
C17 C 0.5306(5) 0.1920(7) 0.4054(4) 0.0511(16) Uani 1 1 d . . . . .
H17 H 0.5371 0.1518 0.3522 0.061 Uiso 1 1 calc R U . . .
C18 C 0.3567(5) 0.0960(7) 0.3915(3) 0.0453(14) Uani 1 1 d . . . . .
C19 C 0.5052(5) 0.3765(8) 0.6507(4) 0.0530(16) Uani 1 1 d . . . . .
H7A H 0.684(7) 0.300(12) 0.721(5) 0.11(3) Uiso 1 1 d . . . . .
H7B H 0.690(6) 0.133(10) 0.719(5) 0.08(2) Uiso 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
Cu1 N2 1.971(5) . ?
Cu1 N2 1.971(5) 3_556 ?
Cu1 N1 2.029(5) 3_556 ?
Cu1 N1 2.029(5) . ?
O1 C6 1.434(6) . ?
O2 C6 1.388(6) . ?
O3 C18 1.259(7) . ?
O4 C18 1.270(7) . ?
O5 C19 1.297(8) . ?
O6 C19 1.215(8) . ?
N1 C1 1.336(7) . ?
N1 C5 1.361(7) . ?
N2 C11 1.343(8) . ?
N2 C7 1.341(7) . ?
C1 C2 1.391(8) . ?
C2 C3 1.391(9) . ?
C3 C4 1.373(9) . ?
C4 C5 1.392(8) . ?
C5 C6 1.531(8) . ?
C6 C7 1.499(9) . ?
C7 C8 1.374(8) . ?
C8 C9 1.371(9) . ?
C9 C10 1.393(9) . ?
C10 C11 1.390(8) . ?
C12 C17 1.396(9) . ?
C12 C13 1.396(8) . ?
C12 C18 1.489(9) . ?
C13 C14 1.380(8) . ?
C14 C15 1.396(9) . ?
C14 C19 1.500(8) . ?
C15 C16 1.391(9) . ?
C16 C17 1.378(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N2 180.00(17) . 3_556 ?
N2 Cu1 N1 91.55(19) . 3_556 ?
N2 Cu1 N1 88.45(19) 3_556 3_556 ?
N2 Cu1 N1 88.46(19) . . ?
N2 Cu1 N1 91.54(19) 3_556 . ?
N1 Cu1 N1 180.0 3_556 . ?
C1 N1 C5 119.4(5) . . ?
C1 N1 Cu1 125.4(4) . . ?
C5 N1 Cu1 115.2(3) . . ?
C11 N2 C7 118.7(5) . . ?
C11 N2 Cu1 123.9(4) . . ?
C7 N2 Cu1 117.4(4) . . ?
N1 C1 C2 122.3(6) . . ?
C3 C2 C1 118.4(6) . . ?
C4 C3 C2 119.6(6) . . ?
C3 C4 C5 119.6(6) . . ?
N1 C5 C4 120.8(5) . . ?
N1 C5 C6 114.4(5) . . ?
C4 C5 C6 124.8(5) . . ?
O2 C6 O1 113.7(4) . . ?
O2 C6 C7 107.0(5) . . ?
O1 C6 C7 105.8(4) . . ?
O2 C6 C5 113.0(5) . . ?
O1 C6 C5 107.9(4) . . ?
C7 C6 C5 109.0(4) . . ?
N2 C7 C8 122.9(6) . . ?
N2 C7 C6 114.3(5) . . ?
C8 C7 C6 122.8(5) . . ?
C9 C8 C7 118.4(5) . . ?
C8 C9 C10 119.9(6) . . ?
C11 C10 C9 118.1(6) . . ?
N2 C11 C10 121.8(5) . . ?
C17 C12 C13 118.8(6) . . ?
C17 C12 C18 120.1(5) . . ?
C13 C12 C18 121.1(5) . . ?
C14 C13 C12 120.9(6) . . ?
C13 C14 C15 120.0(5) . . ?
C13 C14 C19 121.7(6) . . ?
C15 C14 C19 118.3(6) . . ?
C16 C15 C14 119.2(6) . . ?
C15 C16 C17 120.7(6) . . ?
C12 C17 C16 120.4(6) . . ?
O3 C18 O4 122.9(6) . . ?
O3 C18 C12 118.8(5) . . ?
O4 C18 C12 118.3(6) . . ?
O6 C19 O5 123.1(6) . . ?
O6 C19 C14 123.8(6) . . ?
O5 C19 C14 113.1(6) . . ?

_refine_diff_density_max         0.758
_refine_diff_density_min         -1.215
_refine_diff_density_rms         0.101

####################################################################### 
# 
# 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_fid1056cl_0m
_database_code_depnum_ccdc_archive 'CCDC 1033366'
_audit_update_record             
;
2016-03-14 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H42 Cu N4 O22'
_chemical_formula_weight         994.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.658(5)
_cell_length_b                   8.814(5)
_cell_length_c                   13.685(5)
_cell_angle_alpha                99.284(5)
_cell_angle_beta                 95.029(5)
_cell_angle_gamma                102.349(5)
_cell_volume                     998.7(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4348
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.01

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             515
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.8602
_exptl_absorpt_correction_T_max  0.9323
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 SMART APEX2 CCD'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7662
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3507
_reflns_number_gt                3118
_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)+(0.0457P)²+0.3778P] 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         3507
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1174(3) 0.0524(3) 0.80803(16) 0.0322(5) Uani 1 1 d . . .
H1 H 1.0357 -0.0342 0.7786 0.039 Uiso 1 1 calc R . .
C2 C 1.2124(3) 0.1277(3) 0.74902(17) 0.0361(5) Uani 1 1 d . . .
H2 H 1.1956 0.0942 0.6801 0.043 Uiso 1 1 calc R . .
C3 C 1.3317(3) 0.2519(3) 0.79150(17) 0.0348(5) Uani 1 1 d . . .
H3 H 1.3986 0.3057 0.7524 0.042 Uiso 1 1 calc R . .
C4 C 1.3530(3) 0.2973(2) 0.89189(16) 0.0305(5) Uani 1 1 d . . .
H4 H 1.4356 0.3820 0.9229 0.037 Uiso 1 1 calc R . .
C5 C 1.2529(2) 0.2181(2) 0.94628(15) 0.0252(4) Uani 1 1 d . . .
C6 C 1.2584(2) 0.2609(2) 1.05659(15) 0.0271(4) Uani 1 1 d . . .
C7 C 1.1122(2) 0.3209(2) 1.07764(15) 0.0273(4) Uani 1 1 d . . .
C8 C 1.1127(3) 0.4708(3) 1.11735(16) 0.0365(5) Uani 1 1 d . . .
H8 H 1.2080 0.5469 1.1349 0.044 Uiso 1 1 calc R . .
C9 C 0.9717(3) 0.5086(3) 1.13129(18) 0.0428(6) Uani 1 1 d . . .
H9 H 0.9695 0.6114 1.1595 0.051 Uiso 1 1 calc R . .
C10 C 0.8352(3) 0.3981(3) 1.10451(18) 0.0416(6) Uani 1 1 d . . .
H10 H 0.7377 0.4232 1.1129 0.050 Uiso 1 1 calc R . .
C11 C 0.8422(3) 0.2504(3) 1.06537(18) 0.0367(5) Uani 1 1 d . . .
H11 H 0.7480 0.1731 1.0469 0.044 Uiso 1 1 calc R . .
C12 C 1.0601(2) 0.3138(3) 0.53483(16) 0.0318(5) Uani 1 1 d . . .
C13 C 1.1079(3) 0.2736(3) 0.44427(16) 0.0333(5) Uani 1 1 d . . .
H13 H 1.0560 0.1784 0.4031 0.040 Uiso 1 1 calc R . .
C14 C 1.2297(2) 0.3698(3) 0.41303(16) 0.0305(5) Uani 1 1 d . . .
C15 C 1.3051(2) 0.5079(3) 0.47334(16) 0.0311(5) Uani 1 1 d . . .
H15 H 1.3875 0.5758 0.4519 0.037 Uiso 1 1 calc R . .
C16 C 1.2608(2) 0.5477(3) 0.56524(15) 0.0308(5) Uani 1 1 d . . .
C17 C 1.1376(2) 0.4506(3) 0.59578(16) 0.0324(5) Uani 1 1 d . . .
H17 H 1.1068 0.4781 0.6584 0.039 Uiso 1 1 calc R . .
C18 C 0.9228(3) 0.2101(3) 0.56293(17) 0.0362(5) Uani 1 1 d . . .
C19 C 1.2795(3) 0.3268(3) 0.31423(16) 0.0328(5) Uani 1 1 d . . .
C20 C 1.3469(3) 0.6946(3) 0.62913(16) 0.0337(5) Uani 1 1 d . . .
N1 N 1.13629(19) 0.09690(19) 0.90513(12) 0.0261(4) Uani 1 1 d . . .
N2 N 0.9781(2) 0.2121(2) 1.05248(13) 0.0282(4) Uani 1 1 d . . .
O1 O 1.24763(16) 0.12144(17) 1.09309(11) 0.0281(3) Uani 1 1 d . . .
O2 O 1.39467(18) 0.36917(19) 1.09376(13) 0.0358(4) Uani 1 1 d . . .
O3 O 0.8958(2) 0.2519(2) 0.65311(13) 0.0498(5) Uani 1 1 d . . .
O4 O 0.8443(2) 0.0988(2) 0.50760(14) 0.0569(5) Uani 1 1 d . . .
O5 O 1.21943(19) 0.18892(18) 0.26984(11) 0.0400(4) Uani 1 1 d . . .
O6 O 1.37135(19) 0.42479(19) 0.28156(11) 0.0395(4) Uani 1 1 d . . .
O7 O 1.45148(19) 0.78492(19) 0.60469(12) 0.0409(4) Uani 1 1 d . . .
O8 O 1.2986(2) 0.7158(2) 0.71562(13) 0.0530(5) Uani 1 1 d . . .
O9 O 1.4673(2) 0.9516(3) 0.84795(15) 0.0439(4) Uani 1 1 d . . .
O10 O 1.4260(3) 0.1391(3) 0.56706(15) 0.0549(6) Uani 1 1 d . . .
O11 O 0.6433(3) 0.0872(3) 0.70026(18) 0.0504(5) Uani 1 1 d . . .
Cu1 Cu 1.0000 0.0000 1.0000 0.02623(13) Uani 1 2 d S . .
H1A H 1.241(3) 0.145(3) 1.159(2) 0.058(8) Uiso 1 1 d . . .
H2A H 1.392(4) 0.384(4) 1.150(3) 0.058(10) Uiso 1 1 d . . .
H9A H 1.537(4) 0.924(3) 0.873(2) 0.047(9) Uiso 1 1 d . . .
H10A H 1.462(4) 0.161(4) 0.520(3) 0.060(10) Uiso 1 1 d . . .
H3A H 0.815(4) 0.186(4) 0.667(3) 0.085(11) Uiso 1 1 d . . .
H8A H 1.350(4) 0.789(4) 0.748(2) 0.064(10) Uiso 1 1 d . . .
H10B H 1.365(4) 0.073(4) 0.547(3) 0.063(12) Uiso 1 1 d . . .
H9B H 1.509(5) 1.023(5) 0.822(3) 0.095(15) Uiso 1 1 d . . .
H11A H 0.581(4) 0.096(4) 0.666(3) 0.048(12) Uiso 1 1 d . . .
H11B H 0.649(4) 0.004(5) 0.692(3) 0.068(13) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.309(3) . ?
C1 C2 1.351(3) . ?
C2 C3 1.345(3) . ?
C3 C4 1.352(3) . ?
C4 C5 1.347(3) . ?
C5 N1 1.312(3) . ?
C5 C6 1.490(3) . ?
C6 O2 1.348(3) . ?
C6 O1 1.388(3) . ?
C6 C7 1.506(3) . ?
C7 N2 1.317(3) . ?
C7 C8 1.344(3) . ?
C8 C9 1.354(4) . ?
C9 C10 1.340(4) . ?
C10 C11 1.341(3) . ?
C11 N2 1.310(3) . ?
C12 C17 1.353(3) . ?
C12 C13 1.358(3) . ?
C12 C18 1.457(3) . ?
C13 C14 1.352(3) . ?
C14 C15 1.353(3) . ?
C14 C19 1.471(3) . ?
C15 C16 1.361(3) . ?
C16 C17 1.359(3) . ?
C16 C20 1.451(3) . ?
C18 O4 1.176(3) . ?
C18 O3 1.286(3) . ?
C19 O6 1.213(3) . ?
C19 O5 1.246(3) . ?
C20 O7 1.181(3) . ?
C20 O8 1.288(3) . ?
N1 Cu1 2.0006(17) . ?
N2 Cu1 1.947(2) . ?
O1 Cu1 2.3377(17) . ?
Cu1 N2 1.947(2) 2_757 ?
Cu1 N1 2.0006(17) 2_757 ?
Cu1 O1 2.3377(17) 2_757 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.3(2) . . ?
C3 C2 C1 118.9(2) . . ?
C2 C3 C4 119.0(2) . . ?
C5 C4 C3 119.0(2) . . ?
N1 C5 C4 122.2(2) . . ?
N1 C5 C6 113.47(17) . . ?
C4 C5 C6 124.33(19) . . ?
O2 C6 O1 112.76(18) . . ?
O2 C6 C5 109.13(17) . . ?
O1 C6 C5 106.45(16) . . ?
O2 C6 C7 112.53(18) . . ?
O1 C6 C7 107.77(16) . . ?
C5 C6 C7 107.92(17) . . ?
N2 C7 C8 121.2(2) . . ?
N2 C7 C6 113.83(18) . . ?
C8 C7 C6 125.0(2) . . ?
C7 C8 C9 118.6(2) . . ?
C10 C9 C8 120.0(2) . . ?
C9 C10 C11 118.7(2) . . ?
N2 C11 C10 121.8(2) . . ?
C17 C12 C13 119.6(2) . . ?
C17 C12 C18 121.4(2) . . ?
C13 C12 C18 118.9(2) . . ?
C14 C13 C12 121.0(2) . . ?
C13 C14 C15 119.3(2) . . ?
C13 C14 C19 120.8(2) . . ?
C15 C14 C19 119.90(19) . . ?
C14 C15 C16 120.3(2) . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 C20 118.88(19) . . ?
C17 C16 C20 121.1(2) . . ?
C12 C17 C16 119.8(2) . . ?
O4 C18 O3 123.4(2) . . ?
O4 C18 C12 122.6(2) . . ?
O3 C18 C12 113.9(2) . . ?
O6 C19 O5 125.1(2) . . ?
O6 C19 C14 119.5(2) . . ?
O5 C19 C14 115.37(19) . . ?
O7 C20 O8 123.5(2) . . ?
O7 C20 C16 123.5(2) . . ?
O8 C20 C16 113.05(19) . . ?
C1 N1 C5 118.52(18) . . ?
C1 N1 Cu1 126.19(15) . . ?
C5 N1 Cu1 115.28(14) . . ?
C11 N2 C7 119.6(2) . . ?
C11 N2 Cu1 124.66(16) . . ?
C7 N2 Cu1 115.69(14) . . ?
C6 O1 Cu1 93.75(11) . . ?
N2 Cu1 N2 180.0 . 2_757 ?
N2 Cu1 N1 92.94(7) . 2_757 ?
N2 Cu1 N1 87.06(7) 2_757 2_757 ?
N2 Cu1 N1 87.06(7) . . ?
N2 Cu1 N1 92.94(7) 2_757 . ?
N1 Cu1 N1 180.000(1) 2_757 . ?
N2 Cu1 O1 76.36(7) . . ?
N2 Cu1 O1 103.64(7) 2_757 . ?
N1 Cu1 O1 106.00(7) 2_757 . ?
N1 Cu1 O1 74.00(7) . . ?
N2 Cu1 O1 103.64(7) . 2_757 ?
N2 Cu1 O1 76.36(7) 2_757 2_757 ?
N1 Cu1 O1 74.00(7) 2_757 2_757 ?
N1 Cu1 O1 106.00(7) . 2_757 ?
O1 Cu1 O1 180.0 . 2_757 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.049
