# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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. 
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#######################################################################

data_complex5
_database_code_depnum_ccdc_archive 'CCDC 1527820'
_audit_update_record             
;
2017-06-06 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 Cu N O6, H2 O'
_chemical_formula_sum            'C13 H21 Cu N O7'
_chemical_formula_weight         366.85

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.682(5)
_cell_length_b                   26.946(5)
_cell_length_c                   8.247(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.877(5)
_cell_angle_gamma                90
_cell_volume                     1561.0(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.50

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             764
_exptl_transmission_factor_min   0.676
_exptl_transmission_factor_max   0.699
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.432
_shelx_estimated_absorpt_T_min   0.690
_shelx_estimated_absorpt_T_max   0.716
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_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 APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10742
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.096
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4146
_reflns_number_gt                3761
_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+0.4321P] 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         4146
_refine_ls_number_parameters     270
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.155
_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 0.51069(3) 0.44628(2) 0.49212(3) 0.02934(10) Uani 1 1 d . . . . .
O1A O 0.9853(9) 0.3559(3) 0.6785(9) 0.0539(19) Uani 0.310(5) 1 d . . P A 2
H1H1 H 0.996646 0.384835 0.712019 0.081 Uiso 0.310(5) 1 calc R U P A 2
O1 O 0.6980(5) 0.28929(13) 1.0094(4) 0.0669(10) Uani 0.690(5) 1 d . . P A 1
H1 H 0.623398 0.312435 0.969941 0.100 Uiso 0.690(5) 1 calc R U P A 1
O2 O 0.5292(3) 0.36092(8) 0.7975(2) 0.0537(4) Uani 1 1 d . . . . .
O3 O 0.6775(2) 0.39348(6) 0.6388(2) 0.0411(4) Uani 1 1 d . . . . .
O4 O 0.2451(2) 0.41304(7) 0.5652(2) 0.0485(4) Uani 1 1 d . . . . .
H4 H 0.315302 0.394866 0.644428 0.073 Uiso 1 1 calc R U . . .
O5 O 0.3470(2) 0.49996(5) 0.3563(2) 0.0333(3) Uani 1 1 d . . . . .
O6 O 0.7264(3) 0.44468(7) 0.3352(2) 0.0501(4) Uani 1 1 d . . . . .
H6 H 0.792775 0.466073 0.317645 0.075 Uiso 1 1 calc R U . . .
N1 N 0.3674(2) 0.40412(6) 0.2724(2) 0.0327(4) Uani 1 1 d . . . . .
C1 C 0.809(3) 0.3260(10) 0.847(4) 0.031(3) Uani 0.310(5) 1 d . . P A 2
C1A C 0.8410(14) 0.3303(4) 0.8334(16) 0.0304(15) Uani 0.690(5) 1 d . . P A 1
C2 C 0.805(3) 0.2950(10) 0.982(3) 0.047(4) Uani 0.310(5) 1 d . . P A 2
H2 H 0.708999 0.298155 1.023411 0.057 Uiso 0.310(5) 1 calc R U P A 2
C2A C 0.8377(12) 0.2934(4) 0.9544(11) 0.0381(14) Uani 0.690(5) 1 d . . P A 1
C3 C 0.938(3) 0.2616(11) 1.048(4) 0.061(4) Uani 0.310(5) 1 d . . P A 2
H3 H 0.930077 0.239671 1.132099 0.074 Uiso 0.310(5) 1 calc R U P A 2
C3A C 0.9909(11) 0.2596(3) 1.0251(12) 0.0519(18) Uani 0.690(5) 1 d . . P A 1
H3A H 0.993204 0.236138 1.108532 0.062 Uiso 0.690(5) 1 calc R U P A 1
C4 C 1.087(3) 0.2571(8) 1.000(3) 0.056(5) Uani 0.310(5) 1 d . . P A 2
H4A H 1.173761 0.231561 1.049563 0.068 Uiso 0.310(5) 1 calc R U P A 2
C4A C 1.1360(12) 0.2620(4) 0.9693(14) 0.0557(18) Uani 0.690(5) 1 d . . P A 1
H4AA H 1.235742 0.239403 1.013629 0.067 Uiso 0.690(5) 1 calc R U P A 1
C5 C 1.115(4) 0.2888(10) 0.881(4) 0.054(4) Uani 0.310(5) 1 d . . P A 2
H5 H 1.220401 0.287106 0.853436 0.064 Uiso 0.310(5) 1 calc R U P A 2
C5A C 1.1369(15) 0.2978(4) 0.8467(17) 0.0545(18) Uani 0.690(5) 1 d . . P A 1
H5A H 1.236848 0.298857 0.810518 0.065 Uiso 0.690(5) 1 calc R U P A 1
C6 C 0.960(3) 0.3260(9) 0.802(3) 0.035(3) Uani 0.310(5) 1 d . . P A 2
C6A C 0.9923(14) 0.3311(4) 0.7805(15) 0.0380(15) Uani 0.690(5) 1 d . . P A 1
H6A H 0.994041 0.354740 0.698969 0.046 Uiso 0.690(5) 1 calc R U P A 1
C7 C 0.6671(3) 0.36378(8) 0.7530(3) 0.0379(5) Uani 1 1 d . . . . .
C8 C 0.2593(3) 0.36497(9) 0.3180(3) 0.0428(5) Uani 1 1 d . . . . .
H8A H 0.348175 0.340463 0.392618 0.051 Uiso 1 1 calc R U . . .
H8B H 0.175931 0.348450 0.209904 0.051 Uiso 1 1 calc R U . . .
C9 C 0.1412(3) 0.38430(12) 0.4128(4) 0.0547(6) Uani 1 1 d . . . . .
H9A H 0.038469 0.404364 0.330729 0.066 Uiso 1 1 calc R U . . .
H9B H 0.084515 0.356340 0.447553 0.066 Uiso 1 1 calc R U . . .
C10 C 0.2366(3) 0.43833(8) 0.1332(3) 0.0415(5) Uani 1 1 d . . . . .
H10A H 0.108487 0.434971 0.127275 0.050 Uiso 1 1 calc R U . . .
H10B H 0.234349 0.429204 0.018548 0.050 Uiso 1 1 calc R U . . .
C11 C 0.3013(3) 0.49189(8) 0.1742(3) 0.0383(5) Uani 1 1 d . . . . .
H11A H 0.411882 0.497884 0.148285 0.046 Uiso 1 1 calc R U . . .
H11B H 0.200441 0.514231 0.102568 0.046 Uiso 1 1 calc R U . . .
C12 C 0.5049(3) 0.37973(9) 0.2125(3) 0.0423(5) Uani 1 1 d . . . . .
H12A H 0.434818 0.361411 0.104292 0.051 Uiso 1 1 calc R U . . .
H12B H 0.580923 0.356158 0.302039 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6354(4) 0.41629(10) 0.1791(3) 0.0488(6) Uani 1 1 d . . . . .
H13A H 0.729391 0.398802 0.150051 0.059 Uiso 1 1 calc R U . . .
H13B H 0.562799 0.437806 0.080527 0.059 Uiso 1 1 calc R U . . .
O1W O 0.0572(3) 0.48162(8) 0.7107(2) 0.0512(4) Uani 1 1 d G . . . .
H1WA H -0.062423 0.486256 0.669626 0.077 Uiso 1 1 d DG U . . .
H1WB H 0.080902 0.456643 0.659908 0.077 Uiso 1 1 d G 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
Cu1 O5 1.9365(15) 3_666 ?
Cu1 O5 1.9464(15) . ?
Cu1 O3 1.9683(15) . ?
Cu1 N1 2.0422(18) . ?
O1A C6 1.376(15) . ?
O1A H1H1 0.8200 . ?
O1 C2A 1.327(7) . ?
O1 H1 0.8200 . ?
O2 C7 1.257(3) . ?
O3 C7 1.263(3) . ?
O4 C9 1.416(3) . ?
O4 H4 0.8200 . ?
O5 C11 1.414(3) . ?
O6 C13 1.415(3) . ?
O6 H6 0.8200 . ?
N1 C8 1.482(3) . ?
N1 C12 1.488(3) . ?
N1 C10 1.498(3) . ?
C1 C6 1.349(17) . ?
C1 C2 1.40(2) . ?
C1 C7 1.46(3) . ?
C1A C6A 1.397(7) . ?
C1A C2A 1.417(9) . ?
C1A C7 1.524(10) . ?
C2 C3 1.30(3) . ?
C2 H2 0.9300 . ?
C2A C3A 1.413(9) . ?
C3 C4 1.36(2) . ?
C3 H3 0.9300 . ?
C3A C4A 1.368(8) . ?
C3A H3A 0.9300 . ?
C4 C5 1.380(19) . ?
C4 H4A 0.9300 . ?
C4A C5A 1.400(9) . ?
C4A H4AA 0.9300 . ?
C5 C6 1.49(3) . ?
C5 H5 0.9300 . ?
C5A C6A 1.358(12) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C8 C9 1.509(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.519(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.509(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8507 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Cu1 O5 83.10(7) 3_666 . ?
O5 Cu1 O3 94.99(7) 3_666 . ?
O5 Cu1 O3 177.57(6) . . ?
O5 Cu1 N1 161.72(8) 3_666 . ?
O5 Cu1 N1 84.96(7) . . ?
O3 Cu1 N1 97.25(7) . . ?
C6 O1A H1H1 109.5 . . ?
C2A O1 H1 109.5 . . ?
C7 O3 Cu1 133.98(16) . . ?
C9 O4 H4 109.5 . . ?
C11 O5 Cu1 129.30(14) . 3_666 ?
C11 O5 Cu1 108.77(12) . . ?
Cu1 O5 Cu1 96.90(7) 3_666 . ?
C13 O6 H6 109.5 . . ?
C8 N1 C12 108.40(17) . . ?
C8 N1 C10 111.21(17) . . ?
C12 N1 C10 111.30(18) . . ?
C8 N1 Cu1 109.08(14) . . ?
C12 N1 Cu1 109.89(13) . . ?
C10 N1 Cu1 106.94(13) . . ?
C6 C1 C2 121(2) . . ?
C6 C1 C7 113.1(16) . . ?
C2 C1 C7 125.6(17) . . ?
C6A C1A C2A 119.1(7) . . ?
C6A C1A C7 123.2(7) . . ?
C2A C1A C7 117.3(6) . . ?
C3 C2 C1 118.3(18) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
O1 C2A C3A 117.3(7) . . ?
O1 C2A C1A 123.2(7) . . ?
C3A C2A C1A 119.5(7) . . ?
C2 C3 C4 123(2) . . ?
C2 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C4A C3A C2A 119.2(6) . . ?
C4A C3A H3A 120.4 . . ?
C2A C3A H3A 120.4 . . ?
C3 C4 C5 122.8(18) . . ?
C3 C4 H4A 118.6 . . ?
C5 C4 H4A 118.6 . . ?
C3A C4A C5A 121.2(6) . . ?
C3A C4A H4AA 119.4 . . ?
C5A C4A H4AA 119.4 . . ?
C4 C5 C6 113.6(16) . . ?
C4 C5 H5 123.2 . . ?
C6 C5 H5 123.2 . . ?
C6A C5A C4A 120.2(7) . . ?
C6A C5A H5A 119.9 . . ?
C4A C5A H5A 119.9 . . ?
C1 C6 O1A 126.8(18) . . ?
C1 C6 C5 120.2(16) . . ?
O1A C6 C5 112.9(13) . . ?
C5A C6A C1A 120.8(7) . . ?
C5A C6A H6A 119.6 . . ?
C1A C6A H6A 119.6 . . ?
O2 C7 O3 124.9(2) . . ?
O2 C7 C1 109.8(7) . . ?
O3 C7 C1 125.3(7) . . ?
O2 C7 C1A 122.1(3) . . ?
O3 C7 C1A 113.0(3) . . ?
N1 C8 C9 113.7(2) . . ?
N1 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
O4 C9 C8 114.1(2) . . ?
O4 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
O4 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N1 C10 C11 110.89(16) . . ?
N1 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O5 C11 C10 107.52(18) . . ?
O5 C11 H11A 110.2 . . ?
C10 C11 H11A 110.2 . . ?
O5 C11 H11B 110.2 . . ?
C10 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
N1 C12 C13 112.69(19) . . ?
N1 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N1 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
O6 C13 C12 107.9(2) . . ?
O6 C13 H13A 110.1 . . ?
C12 C13 H13A 110.1 . . ?
O6 C13 H13B 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
H1WA O1W H1WB 109.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -9(5) . . . . ?
C7 C1 C2 C3 177(3) . . . . ?
C6A C1A C2A O1 -178.8(10) . . . . ?
C7 C1A C2A O1 -5.0(16) . . . . ?
C6A C1A C2A C3A 2.8(17) . . . . ?
C7 C1A C2A C3A 176.6(9) . . . . ?
C1 C2 C3 C4 4(5) . . . . ?
O1 C2A C3A C4A 178.7(8) . . . . ?
C1A C2A C3A C4A -2.7(15) . . . . ?
C2 C3 C4 C5 2(5) . . . . ?
C2A C3A C4A C5A 1.4(15) . . . . ?
C3 C4 C5 C6 -4(4) . . . . ?
C3A C4A C5A C6A -0.1(19) . . . . ?
C2 C1 C6 O1A -177(3) . . . . ?
C7 C1 C6 O1A -2(4) . . . . ?
C2 C1 C6 C5 7(4) . . . . ?
C7 C1 C6 C5 -178(3) . . . . ?
C4 C5 C6 C1 -1(4) . . . . ?
C4 C5 C6 O1A -177(2) . . . . ?
C4A C5A C6A C1A 0(2) . . . . ?
C2A C1A C6A C5A -1.5(19) . . . . ?
C7 C1A C6A C5A -174.9(13) . . . . ?
Cu1 O3 C7 O2 2.2(4) . . . . ?
Cu1 O3 C7 C1 179.0(16) . . . . ?
Cu1 O3 C7 C1A -178.4(6) . . . . ?
C6 C1 C7 O2 178.5(19) . . . . ?
C2 C1 C7 O2 -7(3) . . . . ?
C6 C1 C7 O3 1(3) . . . . ?
C2 C1 C7 O3 176(2) . . . . ?
C6A C1A C7 O2 177.0(9) . . . . ?
C2A C1A C7 O2 3.5(14) . . . . ?
C6A C1A C7 O3 -2.4(13) . . . . ?
C2A C1A C7 O3 -176.0(8) . . . . ?
C12 N1 C8 C9 169.2(2) . . . . ?
C10 N1 C8 C9 -68.2(2) . . . . ?
Cu1 N1 C8 C9 49.6(2) . . . . ?
N1 C8 C9 O4 -53.3(3) . . . . ?
C8 N1 C10 C11 138.9(2) . . . . ?
C12 N1 C10 C11 -100.1(2) . . . . ?
Cu1 N1 C10 C11 20.0(2) . . . . ?
Cu1 O5 C11 C10 164.76(14) 3_666 . . . ?
Cu1 O5 C11 C10 48.5(2) . . . . ?
N1 C10 C11 O5 -45.2(3) . . . . ?
C8 N1 C12 C13 -174.59(19) . . . . ?
C10 N1 C12 C13 62.8(2) . . . . ?
Cu1 N1 C12 C13 -55.5(2) . . . . ?
N1 C12 C13 O6 55.0(3) . . . . ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_complex1
_database_code_depnum_ccdc_archive 'CCDC 1527817'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 Cu2 N2 O6'
_chemical_formula_weight         517.51

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                   12.8083(8)
_cell_length_b                   8.4214(5)
_cell_length_c                   10.2651(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.604(3)
_cell_angle_gamma                90
_cell_volume                     1076.17(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   0.608
_exptl_transmission_factor_max   0.710
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    2.015
_shelx_estimated_absorpt_T_min   0.602
_shelx_estimated_absorpt_T_max   0.726
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_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 APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28243
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.920
_diffrn_reflns_theta_max         25.074
_diffrn_reflns_theta_full        25.074
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1911
_reflns_number_gt                1706
_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      'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0251P)²+0.6965P] 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         1911
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0590
_refine_ls_wR_factor_gt          0.0568
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.36088(19) 0.7737(3) 0.6976(2) 0.0452(6) Uani 1 1 d . . . . .
H1C H 0.327144 0.688917 0.634909 0.054 Uiso 1 1 calc R U . . .
H1D H 0.378811 0.863026 0.644008 0.054 Uiso 1 1 calc R U . . .
C2 C 0.28252(18) 0.8299(3) 0.7772(2) 0.0432(5) Uani 1 1 d . . . . .
H2A H 0.281169 0.751756 0.848837 0.052 Uiso 1 1 calc R U . . .
H2B H 0.209650 0.833751 0.717306 0.052 Uiso 1 1 calc R U . . .
C3 C 0.30970(18) 0.9916(3) 0.8400(2) 0.0455(6) Uani 1 1 d . . . . .
H3A H 0.306096 1.071519 0.768389 0.055 Uiso 1 1 calc R U . . .
H3B H 0.255880 1.020692 0.891069 0.055 Uiso 1 1 calc R U . . .
C4 C 0.66895(17) 0.6449(2) 1.0818(2) 0.0352(5) Uani 1 1 d . . . . .
C5 C 0.77579(17) 0.5730(2) 1.1465(2) 0.0354(5) Uani 1 1 d . . . . .
C6 C 0.8032(2) 0.5546(3) 1.2844(2) 0.0498(6) Uani 1 1 d . . . . .
H6 H 0.756657 0.593638 1.336672 0.060 Uiso 1 1 calc R U . . .
C7 C 0.8977(2) 0.4801(4) 1.3461(3) 0.0672(8) Uani 1 1 d . . . . .
H7 H 0.916347 0.469189 1.440902 0.081 Uiso 1 1 calc R U . . .
C8 C 0.9645(2) 0.4219(4) 1.2717(3) 0.0738(9) Uani 1 1 d . . . . .
H8 H 1.028881 0.368740 1.314406 0.089 Uiso 1 1 calc R U . . .
C9 C 0.9383(2) 0.4405(4) 1.1343(3) 0.0684(8) Uani 1 1 d . . . . .
H9 H 0.984687 0.399809 1.082458 0.082 Uiso 1 1 calc R U . . .
C10 C 0.84467(19) 0.5183(3) 1.0718(3) 0.0496(6) Uani 1 1 d . . . . .
H10 H 0.827954 0.533873 0.977546 0.060 Uiso 1 1 calc R U . . .
N1 N 0.46033(17) 0.7124(3) 0.7873(2) 0.0402(5) Uani 1 1 d . . . . .
O1 O 0.41356(12) 0.99425(18) 0.92698(16) 0.0441(4) Uani 1 1 d . . . . .
O2 O 0.66282(12) 0.72353(19) 0.97439(15) 0.0422(4) Uani 1 1 d . . . . .
O3 O 0.59253(12) 0.62612(18) 1.13523(16) 0.0432(4) Uani 1 1 d . . . . .
Cu1 Cu 0.53017(2) 0.84828(3) 0.93833(3) 0.03459(10) Uani 1 1 d . . . . .
H1A H 0.449(2) 0.622(3) 0.817(3) 0.052 Uiso 1 1 d . U . . .
H1B H 0.506(2) 0.697(3) 0.745(3) 0.052 Uiso 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 1.479(3) . ?
C1 C2 1.511(3) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C2 C3 1.512(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O1 1.417(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O3 1.240(3) . ?
C4 O2 1.272(3) . ?
C4 C5 1.501(3) . ?
C5 C10 1.377(3) . ?
C5 C6 1.384(3) . ?
C6 C7 1.378(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.366(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
N1 Cu1 1.965(2) . ?
N1 H1A 0.84(3) . ?
N1 H1B 0.82(3) . ?
O1 Cu1 1.9167(15) . ?
O1 Cu1 1.9289(15) 3_677 ?
O2 Cu1 1.9574(15) . ?
Cu1 Cu1 3.0316(5) 3_677 ?

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 110.91(19) . . ?
N1 C1 H1C 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
C2 C1 H1D 109.5 . . ?
H1C C1 H1D 108.0 . . ?
C1 C2 C3 113.4(2) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
O1 C3 C2 111.78(19) . . ?
O1 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
O1 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
O3 C4 O2 123.7(2) . . ?
O3 C4 C5 119.0(2) . . ?
O2 C4 C5 117.24(19) . . ?
C10 C5 C6 119.3(2) . . ?
C10 C5 C4 121.7(2) . . ?
C6 C5 C4 118.9(2) . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 119.9(2) . . ?
C5 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C1 N1 Cu1 116.97(16) . . ?
C1 N1 H1A 110.3(18) . . ?
Cu1 N1 H1A 108.8(18) . . ?
C1 N1 H1B 110.2(19) . . ?
Cu1 N1 H1B 105(2) . . ?
H1A N1 H1B 105(3) . . ?
C3 O1 Cu1 129.09(14) . . ?
C3 O1 Cu1 126.84(14) . 3_677 ?
Cu1 O1 Cu1 104.06(7) . 3_677 ?
C4 O2 Cu1 108.49(13) . . ?
O1 Cu1 O1 75.94(7) . 3_677 ?
O1 Cu1 O2 170.07(7) . . ?
O1 Cu1 O2 94.13(7) 3_677 . ?
O1 Cu1 N1 97.01(8) . . ?
O1 Cu1 N1 171.87(7) 3_677 . ?
O2 Cu1 N1 92.89(8) . . ?
O1 Cu1 Cu1 38.11(4) . 3_677 ?
O1 Cu1 Cu1 37.83(4) 3_677 3_677 ?
O2 Cu1 Cu1 131.96(5) . 3_677 ?
N1 Cu1 Cu1 134.99(6) . 3_677 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 78.5(3) . . . . ?
C1 C2 C3 O1 -58.5(3) . . . . ?
O3 C4 C5 C10 147.1(2) . . . . ?
O2 C4 C5 C10 -33.5(3) . . . . ?
O3 C4 C5 C6 -29.8(3) . . . . ?
O2 C4 C5 C6 149.6(2) . . . . ?
C10 C5 C6 C7 -1.0(4) . . . . ?
C4 C5 C6 C7 175.9(2) . . . . ?
C5 C6 C7 C8 -0.8(4) . . . . ?
C6 C7 C8 C9 1.2(5) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C6 C5 C10 C9 2.4(4) . . . . ?
C4 C5 C10 C9 -174.5(2) . . . . ?
C8 C9 C10 C5 -2.0(5) . . . . ?
C2 C1 N1 Cu1 -50.1(2) . . . . ?
C2 C3 O1 Cu1 17.4(3) . . . . ?
C2 C3 O1 Cu1 -163.41(15) . . . 3_677 ?
O3 C4 O2 Cu1 14.1(3) . . . . ?
C5 C4 O2 Cu1 -165.23(14) . . . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_complex3
_database_code_depnum_ccdc_archive 'CCDC 1527819'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 Cu2 N2 O8'
_chemical_formula_weight         577.56

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   29.866(4)
_cell_length_b                   8.1887(9)
_cell_length_c                   10.1006(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.706(11)
_cell_angle_gamma                90
_cell_volume                     2461.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25.50

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   0.646
_exptl_transmission_factor_max   0.739
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.776
_shelx_estimated_absorpt_T_min   0.618
_shelx_estimated_absorpt_T_max   0.752
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_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 APEX'
_diffrn_measurement_method       /w-scans

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16780
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.580
_diffrn_reflns_theta_max         25.045
_diffrn_reflns_theta_full        25.045
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2173
_reflns_number_gt                1772
_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      'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+2.2278P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2173
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.23577(2) 1.09761(4) 0.42204(3) 0.03490(13) Uani 1 1 d . . . . .
O4 O -0.00733(9) 0.7168(5) 0.5684(3) 0.0991(11) Uani 1 1 d . . . . .
O3 O 0.20181(7) 0.8665(2) 0.5971(2) 0.0482(5) Uani 1 1 d . . . . .
O2 O 0.17971(7) 0.9793(3) 0.4023(2) 0.0454(5) Uani 1 1 d . . . . .
O1 O 0.28587(6) 1.2421(2) 0.45661(19) 0.0401(5) Uani 1 1 d . . . . .
N1 N 0.26401(8) 0.9560(3) 0.2957(2) 0.0402(6) Uani 1 1 d . . . . .
H1A H 0.269956 0.860559 0.335504 0.048 Uiso 1 1 calc R U . . .
H1B H 0.243867 0.937218 0.227539 0.048 Uiso 1 1 calc R U . . .
C4 C 0.17223(10) 0.8997(3) 0.5079(3) 0.0379(7) Uani 1 1 d . . . . .
C5 C 0.12441(10) 0.8506(3) 0.5203(3) 0.0383(7) Uani 1 1 d . . . . .
C10 C 0.10969(10) 0.8131(4) 0.6433(3) 0.0464(7) Uani 1 1 d . . . . .
H10 H 0.129893 0.816305 0.718415 0.056 Uiso 1 1 calc R U . . .
C9 C 0.06563(11) 0.7713(5) 0.6560(3) 0.0599(9) Uani 1 1 d . . . . .
H9 H 0.056178 0.747982 0.739367 0.072 Uiso 1 1 calc R U . . .
C8 C 0.03553(11) 0.7641(5) 0.5456(4) 0.0644(10) Uani 1 1 d . . . . .
C7 C 0.04900(12) 0.8042(6) 0.4226(4) 0.0734(12) Uani 1 1 d . . . . .
H7 H 0.028544 0.802018 0.348080 0.088 Uiso 1 1 calc R U . . .
C6 C 0.09336(11) 0.8479(5) 0.4109(3) 0.0590(9) Uani 1 1 d . . . . .
H6 H 0.102398 0.875970 0.327946 0.071 Uiso 1 1 calc R U . . .
C11 C -0.04043(13) 0.7118(8) 0.4583(5) 0.121(2) Uani 1 1 d . . . . .
H11A H -0.042680 0.817265 0.416866 0.181 Uiso 1 1 calc R U . . .
H11B H -0.068954 0.682404 0.488854 0.181 Uiso 1 1 calc R U . . .
H11C H -0.031929 0.632258 0.395210 0.181 Uiso 1 1 calc R U . . .
C3 C 0.30595(10) 1.0142(4) 0.2413(3) 0.0469(8) Uani 1 1 d . . . . .
H3A H 0.299055 1.104328 0.180710 0.056 Uiso 1 1 calc R U . . .
H3B H 0.318846 0.926682 0.191961 0.056 Uiso 1 1 calc R U . . .
C2 C 0.33951(10) 1.0693(4) 0.3528(3) 0.0448(7) Uani 1 1 d . . . . .
H2A H 0.340258 0.989187 0.423694 0.054 Uiso 1 1 calc R U . . .
H2B H 0.369143 1.072451 0.320091 0.054 Uiso 1 1 calc R U . . .
C1 C 0.32936(9) 1.2346(4) 0.4091(3) 0.0460(8) Uani 1 1 d . . . . .
H1C H 0.351688 1.259703 0.481419 0.055 Uiso 1 1 calc R U . . .
H1D H 0.331551 1.316784 0.340769 0.055 Uiso 1 1 calc R 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
Cu1 O1 1.9171(18) . ?
Cu1 O2 1.9307(19) . ?
Cu1 O1 1.9425(18) 7_576 ?
Cu1 N1 1.965(2) . ?
Cu1 Cu1 3.0351(7) 7_576 ?
O4 C8 1.375(4) . ?
O4 C11 1.427(5) . ?
O3 C4 1.239(4) . ?
O2 C4 1.285(3) . ?
O1 C1 1.422(3) . ?
N1 C3 1.487(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C4 C5 1.499(4) . ?
C5 C6 1.383(4) . ?
C5 C10 1.386(4) . ?
C10 C9 1.376(4) . ?
C10 H10 0.9300 . ?
C9 C8 1.375(5) . ?
C9 H9 0.9300 . ?
C8 C7 1.377(5) . ?
C7 C6 1.387(4) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C3 C2 1.514(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 C1 1.509(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?

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 O2 170.39(8) . . ?
O1 Cu1 O1 76.31(8) . 7_576 ?
O2 Cu1 O1 94.24(8) . 7_576 ?
O1 Cu1 N1 96.43(9) . . ?
O2 Cu1 N1 92.95(9) . . ?
O1 Cu1 N1 172.46(9) 7_576 . ?
O1 Cu1 Cu1 38.45(5) . 7_576 ?
O2 Cu1 Cu1 132.07(6) . 7_576 ?
O1 Cu1 Cu1 37.86(5) 7_576 7_576 ?
N1 Cu1 Cu1 134.85(7) . 7_576 ?
C8 O4 C11 118.2(3) . . ?
C4 O2 Cu1 112.13(18) . . ?
C1 O1 Cu1 129.25(17) . . ?
C1 O1 Cu1 127.03(17) . 7_576 ?
Cu1 O1 Cu1 103.70(8) . 7_576 ?
C3 N1 Cu1 118.09(19) . . ?
C3 N1 H1A 107.8 . . ?
Cu1 N1 H1A 107.8 . . ?
C3 N1 H1B 107.8 . . ?
Cu1 N1 H1B 107.8 . . ?
H1A N1 H1B 107.1 . . ?
O3 C4 O2 123.6(3) . . ?
O3 C4 C5 120.5(3) . . ?
O2 C4 C5 115.9(3) . . ?
C6 C5 C10 118.1(3) . . ?
C6 C5 C4 121.3(3) . . ?
C10 C5 C4 120.6(3) . . ?
C9 C10 C5 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C8 O4 115.6(3) . . ?
C9 C8 C7 120.1(3) . . ?
O4 C8 C7 124.3(3) . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C5 C6 C7 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C3 C2 110.3(2) . . ?
N1 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C1 C2 C3 114.0(3) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.6 . . ?
O1 C1 C2 112.5(2) . . ?
O1 C1 H1C 109.1 . . ?
C2 C1 H1C 109.1 . . ?
O1 C1 H1D 109.1 . . ?
C2 C1 H1D 109.1 . . ?
H1C C1 H1D 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O2 C4 O3 -18.1(3) . . . . ?
Cu1 O2 C4 C5 160.55(18) . . . . ?
O3 C4 C5 C6 -163.2(3) . . . . ?
O2 C4 C5 C6 18.1(4) . . . . ?
O3 C4 C5 C10 19.5(4) . . . . ?
O2 C4 C5 C10 -159.2(3) . . . . ?
C6 C5 C10 C9 1.3(5) . . . . ?
C4 C5 C10 C9 178.6(3) . . . . ?
C5 C10 C9 C8 0.9(6) . . . . ?
C10 C9 C8 O4 178.3(4) . . . . ?
C10 C9 C8 C7 -2.3(6) . . . . ?
C11 O4 C8 C9 178.1(5) . . . . ?
C11 O4 C8 C7 -1.3(7) . . . . ?
C9 C8 C7 C6 1.6(7) . . . . ?
O4 C8 C7 C6 -179.1(4) . . . . ?
C10 C5 C6 C7 -2.0(5) . . . . ?
C4 C5 C6 C7 -179.3(3) . . . . ?
C8 C7 C6 C5 0.6(6) . . . . ?
Cu1 N1 C3 C2 50.3(3) . . . . ?
N1 C3 C2 C1 -76.9(3) . . . . ?
Cu1 O1 C1 C2 -16.3(4) . . . . ?
Cu1 O1 C1 C2 161.9(2) 7_576 . . . ?
C3 C2 C1 O1 57.1(4) . . . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.223
_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_Complex2
_database_code_depnum_ccdc_archive 'CCDC 1527818'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 Cu2 N2 O8'
_chemical_formula_weight         577.56

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                   14.7617(11)
_cell_length_b                   8.5963(7)
_cell_length_c                   10.0181(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.639(3)
_cell_angle_gamma                90
_cell_volume                     1197.31(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      25.50

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   0.637
_exptl_transmission_factor_max   0.747
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.826
_shelx_estimated_absorpt_T_min   0.629
_shelx_estimated_absorpt_T_max   0.759
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_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 APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29364
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.786
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.671
_diffrn_measured_fraction_theta_full 0.671
_diffrn_reflns_Laue_measured_fraction_max 0.671
_diffrn_reflns_Laue_measured_fraction_full 0.671
_diffrn_reflns_point_group_measured_fraction_max 0.671
_diffrn_reflns_point_group_measured_fraction_full 0.671
_reflns_number_total             1420
_reflns_number_gt                1281
_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      'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.2276P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1420
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0716
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.30291(19) 0.3347(3) 0.5615(3) 0.0370(6) Uani 1 1 d . . . . .
H1A H 0.237693 0.339829 0.568644 0.044 Uiso 1 1 calc R U . . .
H1B H 0.300941 0.258706 0.486312 0.044 Uiso 1 1 calc R U . . .
C2 C 0.37201(19) 0.2772(3) 0.7000(3) 0.0390(6) Uani 1 1 d . . . . .
H2A H 0.389146 0.363973 0.768974 0.047 Uiso 1 1 calc R U . . .
H2B H 0.340670 0.195091 0.738340 0.047 Uiso 1 1 calc R U . . .
C3 C 0.67149(18) 0.5072(3) 0.4815(3) 0.0393(6) Uani 1 1 d . . . . .
H3A H 0.674872 0.428990 0.410761 0.047 Uiso 1 1 calc R U . . .
H3B H 0.719033 0.477908 0.574136 0.047 Uiso 1 1 calc R U . . .
C4 C 0.65025(19) 0.1459(2) 0.5418(3) 0.0306(6) Uani 1 1 d . . . . .
C5 C 0.74657(17) 0.0723(3) 0.5608(3) 0.0319(5) Uani 1 1 d . . . . .
C6 C 0.7722(2) 0.0415(3) 0.4417(3) 0.0419(6) Uani 1 1 d . . . . .
H6 H 0.731546 0.071951 0.349961 0.050 Uiso 1 1 calc R U . . .
C7 C 0.8580(2) -0.0343(4) 0.4597(4) 0.0522(8) Uani 1 1 d . . . . .
H7 H 0.876410 -0.054962 0.379185 0.063 Uiso 1 1 calc R U . . .
C8 C 0.9175(2) -0.0804(4) 0.5913(4) 0.0501(8) Uani 1 1 d . . . . .
H8 H 0.975050 -0.135813 0.601105 0.060 Uiso 1 1 calc R U . . .
C9 C 0.8929(2) -0.0454(3) 0.7096(4) 0.0441(7) Uani 1 1 d . . . . .
C10 C 0.80680(18) 0.0323(3) 0.6932(3) 0.0374(6) Uani 1 1 d . . . . .
H10 H 0.789941 0.057609 0.774199 0.045 Uiso 1 1 calc R U . . .
C11 C 1.0409(3) -0.1401(6) 0.8737(6) 0.0826(15) Uani 1 1 d . . . . .
H11A H 1.071784 -0.155542 0.975909 0.124 Uiso 1 1 calc R U . . .
H11B H 1.078334 -0.065279 0.839736 0.124 Uiso 1 1 calc R U . . .
H11C H 1.037881 -0.239479 0.824520 0.124 Uiso 1 1 calc R U . . .
N1 N 0.46132(15) 0.2135(3) 0.6819(2) 0.0346(5) Uani 1 1 d . . . . .
H1C H 0.446209 0.122543 0.632966 0.042 Uiso 1 1 calc R U . . .
H1D H 0.503864 0.190890 0.769207 0.042 Uiso 1 1 calc R U . . .
O1 O 0.57816(12) 0.5056(2) 0.4918(2) 0.0390(4) Uani 1 1 d . . . . .
O2 O 0.64387(13) 0.2267(2) 0.6447(2) 0.0386(4) Uani 1 1 d . . . . .
O3 O 0.58293(15) 0.1251(2) 0.4290(2) 0.0431(5) Uani 1 1 d . . . . .
O4 O 0.94670(17) -0.0821(4) 0.8461(3) 0.0710(8) Uani 1 1 d . . . . .
Cu1 Cu 0.52586(2) 0.34983(3) 0.58360(3) 0.02908(14) 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 C2 1.503(4) . ?
C1 C3 1.511(4) 3_666 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.494(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O1 1.416(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O3 1.242(4) . ?
C4 O2 1.273(3) . ?
C4 C5 1.509(3) . ?
C5 C10 1.370(4) . ?
C5 C6 1.393(4) . ?
C6 C7 1.381(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(5) . ?
C8 H8 0.9500 . ?
C9 O4 1.368(4) . ?
C9 C10 1.395(4) . ?
C10 H10 0.9500 . ?
C11 O4 1.414(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N1 Cu1 1.970(2) . ?
N1 H1C 0.9100 . ?
N1 H1D 0.9100 . ?
O1 Cu1 1.9220(18) 3_666 ?
O1 Cu1 1.9266(17) . ?
O2 Cu1 1.9528(17) . ?
Cu1 Cu1 3.0323(6) 3_666 ?

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
C2 C1 C3 113.7(2) . 3_666 ?
C2 C1 H1A 108.8 . . ?
C3 C1 H1A 108.8 3_666 . ?
C2 C1 H1B 108.8 . . ?
C3 C1 H1B 108.8 3_666 . ?
H1A C1 H1B 107.7 . . ?
N1 C2 C1 111.2(2) . . ?
N1 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O1 C3 C1 111.9(2) . 3_666 ?
O1 C3 H3A 109.2 . . ?
C1 C3 H3A 109.2 3_666 . ?
O1 C3 H3B 109.2 . . ?
C1 C3 H3B 109.2 3_666 . ?
H3A C3 H3B 107.9 . . ?
O3 C4 O2 124.2(2) . . ?
O3 C4 C5 119.1(2) . . ?
O2 C4 C5 116.7(2) . . ?
C10 C5 C6 120.5(2) . . ?
C10 C5 C4 120.3(2) . . ?
C6 C5 C4 119.2(3) . . ?
C7 C6 C5 118.6(3) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C6 121.5(3) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 119.5(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
O4 C9 C8 125.0(3) . . ?
O4 C9 C10 115.3(3) . . ?
C8 C9 C10 119.6(3) . . ?
C5 C10 C9 120.2(3) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 N1 Cu1 115.93(17) . . ?
C2 N1 H1C 108.3 . . ?
Cu1 N1 H1C 108.3 . . ?
C2 N1 H1D 108.3 . . ?
Cu1 N1 H1D 108.3 . . ?
H1C N1 H1D 107.4 . . ?
C3 O1 Cu1 129.30(17) . 3_666 ?
C3 O1 Cu1 126.71(17) . . ?
Cu1 O1 Cu1 103.98(7) 3_666 . ?
C4 O2 Cu1 110.05(17) . . ?
C9 O4 C11 118.6(4) . . ?
O1 Cu1 O1 76.02(7) 3_666 . ?
O1 Cu1 O2 169.93(7) 3_666 . ?
O1 Cu1 O2 93.91(7) . . ?
O1 Cu1 N1 97.14(8) 3_666 . ?
O1 Cu1 N1 172.18(8) . . ?
O2 Cu1 N1 92.93(8) . . ?
O1 Cu1 Cu1 38.07(5) 3_666 3_666 ?
O1 Cu1 Cu1 37.96(5) . 3_666 ?
O2 Cu1 Cu1 131.86(6) . 3_666 ?
N1 Cu1 Cu1 135.09(7) . 3_666 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 N1 -78.8(3) 3_666 . . . ?
O3 C4 C5 C10 -151.1(3) . . . . ?
O2 C4 C5 C10 29.0(3) . . . . ?
O3 C4 C5 C6 27.0(3) . . . . ?
O2 C4 C5 C6 -152.8(2) . . . . ?
C10 C5 C6 C7 2.0(4) . . . . ?
C4 C5 C6 C7 -176.2(2) . . . . ?
C5 C6 C7 C8 0.5(5) . . . . ?
C6 C7 C8 C9 -2.4(5) . . . . ?
C7 C8 C9 O4 -178.7(3) . . . . ?
C7 C8 C9 C10 1.8(5) . . . . ?
C6 C5 C10 C9 -2.6(4) . . . . ?
C4 C5 C10 C9 175.6(2) . . . . ?
O4 C9 C10 C5 -178.9(3) . . . . ?
C8 C9 C10 C5 0.7(4) . . . . ?
C1 C2 N1 Cu1 51.4(3) . . . . ?
C1 C3 O1 Cu1 17.2(4) 3_666 . . 3_666 ?
C1 C3 O1 Cu1 -164.5(2) 3_666 . . . ?
O3 C4 O2 Cu1 -13.3(3) . . . . ?
C5 C4 O2 Cu1 166.62(15) . . . . ?
C8 C9 O4 C11 9.6(6) . . . . ?
C10 C9 O4 C11 -170.8(4) . . . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.266
_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_complex6
_database_code_depnum_ccdc_archive 'CCDC 1527821'
_audit_update_record             
;
2017-06-06 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H38 Cu2 N2 O12, C12 H26 Cu N2 O6, 2(H2 O)'
_chemical_formula_sum            'C38 H68 Cu3 N4 O20'
_chemical_formula_weight         1091.58

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                   7.6515(2)
_cell_length_b                   7.8302(2)
_cell_length_c                   19.9839(6)
_cell_angle_alpha                93.0960(10)
_cell_angle_beta                 90.4780(10)
_cell_angle_gamma                107.6040(10)
_cell_volume                     1139.17(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_F_000             571
_exptl_transmission_factor_min   0.697
_exptl_transmission_factor_max   0.802
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.470
_shelx_estimated_absorpt_T_min   0.667
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_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 APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56340
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0314
_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       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.734
_diffrn_reflns_theta_max         28.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5703
_reflns_number_gt                5242
_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+0.5888P] 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         5703
_refine_ls_number_parameters     300
_refine_ls_number_restraints     71
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0695
_refine_ls_wR_factor_gt          0.0673
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.47705(2) 0.48551(2) 0.42740(2) 0.01983(6) Uani 1 1 d . U . . .
Cu2 Cu 0.500000 0.500000 0.000000 0.02082(6) Uani 1 2 d S U P . .
O6 O 0.36180(14) 0.35799(13) 0.50397(5) 0.0236(2) Uani 1 1 d . U . . .
O1 O 0.31461(15) 0.31808(16) 0.36142(5) 0.0304(2) Uani 1 1 d . U . . .
O9 O 0.69276(15) 0.70676(15) 0.03875(5) 0.0282(2) Uani 1 1 d . U . . .
O2 O 0.47726(17) 0.16970(17) 0.30352(7) 0.0391(3) Uani 1 1 d . U . . .
O5 O 0.24606(18) 0.64893(17) 0.42314(6) 0.0377(3) Uani 1 1 d . U . . .
H5 H 0.176768 0.674879 0.450173 0.057 Uiso 1 1 calc R U . . .
O8 O 0.28472(18) 0.6398(2) 0.06384(7) 0.0437(3) Uani 1 1 d . U . . .
O4 O 0.74179(17) 0.38661(16) 0.37923(6) 0.0337(2) Uani 1 1 d . U . . .
H4 H 0.665069 0.312047 0.355281 0.051 Uiso 1 1 calc R U . . .
O1W O 0.95821(19) 0.2726(2) 0.47648(7) 0.0443(3) Uani 1 1 d G . . . .
H1WA H 1.072662 0.325440 0.481242 0.066 Uiso 1 1 d G U . . .
H1WB H 0.915927 0.312575 0.443307 0.066 Uiso 1 1 d G U . . .
O3 O -0.29336(18) -0.08918(19) 0.14756(7) 0.0435(3) Uani 1 1 d . U . . .
H3 H -0.371290 -0.043946 0.160914 0.065 Uiso 1 1 calc R U . . .
O7 O 0.91083(17) 0.5257(2) 0.07262(7) 0.0444(3) Uani 1 1 d . U . . .
H7A H 0.845145 0.581917 0.058386 0.067 Uiso 1 1 calc R U . . .
N2 N 0.46586(18) 0.36067(18) 0.08728(6) 0.0268(3) Uani 1 1 d . U . . .
N1 N 0.59019(17) 0.68958(16) 0.36560(6) 0.0226(2) Uani 1 1 d . U . . .
C2 C 0.1650(2) 0.11737(18) 0.27289(7) 0.0215(3) Uani 1 1 d . U . . .
C3 C 0.1679(2) -0.0065(2) 0.22059(7) 0.0263(3) Uani 1 1 d . U . . .
H3A H 0.272611 -0.041529 0.214162 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0055(2) 0.1642(2) 0.28275(7) 0.0264(3) Uani 1 1 d . U . . .
H7 H 0.000889 0.244355 0.318294 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6984(2) 0.6277(2) 0.31381(8) 0.0317(3) Uani 1 1 d . U . . .
H8A H 0.768139 0.730100 0.289981 0.038 Uiso 1 1 calc R U . . .
H8B H 0.614738 0.544644 0.281699 0.038 Uiso 1 1 calc R U . . .
C1 C 0.3332(2) 0.20655(19) 0.31585(7) 0.0227(3) Uani 1 1 d . U . . .
C6 C -0.1464(2) 0.0939(2) 0.24070(8) 0.0292(3) Uani 1 1 d . U . . .
H6 H -0.252029 0.126834 0.247905 0.035 Uiso 1 1 calc R U . . .
C19 C 0.7508(3) 0.8446(2) -0.00648(9) 0.0405(4) Uani 1 1 d . U . . .
H19A H 0.861679 0.836972 -0.027877 0.049 Uiso 1 1 calc R U . . .
H19B H 0.778426 0.960627 0.017878 0.049 Uiso 1 1 calc R U . . .
C10 C 0.4397(2) 0.7383(2) 0.33151(8) 0.0300(3) Uani 1 1 d . U . . .
H10A H 0.368958 0.636816 0.302710 0.036 Uiso 1 1 calc R U . . .
H10B H 0.492640 0.837227 0.303391 0.036 Uiso 1 1 calc R U . . .
C4 C 0.0158(2) -0.0784(2) 0.17779(8) 0.0292(3) Uani 1 1 d . U . . .
H4A H 0.019312 -0.160823 0.142916 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6287(3) 0.3858(3) 0.13261(9) 0.0423(4) Uani 1 1 d . U . . .
H14A H 0.594979 0.297407 0.166195 0.051 Uiso 1 1 calc R U . . .
H14B H 0.656197 0.503216 0.155850 0.051 Uiso 1 1 calc R U . . .
C9 C 0.8292(2) 0.5366(3) 0.34182(10) 0.0393(4) Uani 1 1 d . U . . .
H9A H 0.892438 0.497334 0.305026 0.047 Uiso 1 1 calc R U . . .
H9B H 0.920588 0.623268 0.370413 0.047 Uiso 1 1 calc R U . . .
C5 C -0.1409(2) -0.0270(2) 0.18728(7) 0.0277(3) Uani 1 1 d . U . . .
C11 C 0.3128(2) 0.7916(2) 0.38037(9) 0.0347(4) Uani 1 1 d . U . . .
H11A H 0.378632 0.900622 0.406412 0.042 Uiso 1 1 calc R U . . .
H11B H 0.211603 0.813300 0.356350 0.042 Uiso 1 1 calc R U . . .
C18 C 0.3966(3) 0.1720(2) 0.05914(9) 0.0377(4) Uani 1 1 d . U . . .
H18A H 0.347192 0.092905 0.094675 0.045 Uiso 1 1 calc R U . . .
H18B H 0.496695 0.136420 0.039431 0.045 Uiso 1 1 calc R U . . .
C17 C 0.3189(2) 0.5929(3) 0.12918(9) 0.0373(4) Uani 1 1 d . U . . .
H17A H 0.225597 0.610699 0.158933 0.045 Uiso 1 1 calc R U . . .
H17B H 0.436966 0.670814 0.146016 0.045 Uiso 1 1 calc R U . . .
C16 C 0.3182(2) 0.4016(3) 0.12906(9) 0.0365(4) Uani 1 1 d . U . . .
H16A H 0.199627 0.324815 0.112265 0.044 Uiso 1 1 calc R U . . .
H16B H 0.333627 0.372412 0.174865 0.044 Uiso 1 1 calc R U . . .
C15 C 0.8027(3) 0.3713(3) 0.10054(12) 0.0503(5) Uani 1 1 d . U . . .
H15A H 0.875999 0.337358 0.134188 0.060 Uiso 1 1 calc R U . . .
H15B H 0.769339 0.275148 0.065697 0.060 Uiso 1 1 calc R U . . .
C13 C 0.3397(2) 0.17715(19) 0.51764(7) 0.0278(3) Uani 1 1 d . U . . .
H13A H 0.452474 0.148228 0.509231 0.033 Uiso 1 1 calc R U . . .
H13B H 0.242790 0.097038 0.489123 0.033 Uiso 1 1 calc R U . . .
C12 C 0.7094(2) 0.8439(2) 0.40886(8) 0.0297(3) Uani 1 1 d . U . . .
H12A H 0.694118 0.955196 0.394713 0.036 Uiso 1 1 calc R U . . .
H12B H 0.837026 0.849882 0.403574 0.036 Uiso 1 1 calc R 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
Cu1 O6 1.9419(10) . ?
Cu1 O6 1.9440(10) 2_666 ?
Cu1 O1 1.9501(11) . ?
Cu1 N1 2.0548(12) . ?
Cu1 Cu1 2.9083(3) 2_666 ?
Cu2 O9 1.9486(10) 2_665 ?
Cu2 O9 1.9486(10) . ?
Cu2 N2 2.0836(13) 2_665 ?
Cu2 N2 2.0837(13) . ?
O6 C13 1.4164(17) . ?
O1 C1 1.2663(17) . ?
O9 C19 1.415(2) . ?
O2 C1 1.2443(19) . ?
O5 C11 1.416(2) . ?
O5 H5 0.8200 . ?
O8 C17 1.419(2) . ?
O4 C9 1.419(2) . ?
O4 H4 0.8200 . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8499 . ?
O3 C5 1.3520(19) . ?
O3 H3 0.8200 . ?
O7 C15 1.390(3) . ?
O7 H7A 0.8200 . ?
N2 C18 1.487(2) . ?
N2 C14 1.492(2) . ?
N2 C16 1.510(2) . ?
N1 C8 1.4814(18) . ?
N1 C10 1.4890(19) . ?
N1 C12 1.4992(19) . ?
C2 C7 1.390(2) . ?
C2 C3 1.3917(19) . ?
C2 C1 1.5010(19) . ?
C3 C4 1.392(2) . ?
C3 H3A 0.9300 . ?
C7 C6 1.381(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.513(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 C5 1.397(2) . ?
C6 H6 0.9300 . ?
C19 C18 1.508(3) 2_665 ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C10 C11 1.512(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C4 C5 1.387(2) . ?
C4 H4A 0.9300 . ?
C14 C15 1.514(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17 C16 1.496(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C13 C12 1.524(2) 2_666 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Cu1 O6 83.09(5) . 2_666 ?
O6 Cu1 O1 94.45(5) . . ?
O6 Cu1 O1 177.03(5) 2_666 . ?
O6 Cu1 N1 161.31(5) . . ?
O6 Cu1 N1 84.53(5) 2_666 . ?
O1 Cu1 N1 98.25(5) . . ?
O6 Cu1 Cu1 41.58(3) . 2_666 ?
O6 Cu1 Cu1 41.52(3) 2_666 2_666 ?
O1 Cu1 Cu1 136.01(4) . 2_666 ?
N1 Cu1 Cu1 124.66(3) . 2_666 ?
O9 Cu2 O9 180.0 2_665 . ?
O9 Cu2 N2 94.42(5) 2_665 2_665 ?
O9 Cu2 N2 85.58(5) . 2_665 ?
O9 Cu2 N2 85.58(5) 2_665 . ?
O9 Cu2 N2 94.42(5) . . ?
N2 Cu2 N2 180.0 2_665 . ?
C13 O6 Cu1 127.87(9) . . ?
C13 O6 Cu1 108.91(8) . 2_666 ?
Cu1 O6 Cu1 96.91(4) . 2_666 ?
C1 O1 Cu1 135.54(10) . . ?
C19 O9 Cu2 112.29(10) . . ?
C11 O5 H5 109.5 . . ?
C9 O4 H4 109.5 . . ?
H1WA O1W H1WB 109.5 . . ?
C5 O3 H3 109.5 . . ?
C15 O7 H7A 109.5 . . ?
C18 N2 C14 110.68(14) . . ?
C18 N2 C16 108.78(13) . . ?
C14 N2 C16 107.21(13) . . ?
C18 N2 Cu2 100.98(9) . . ?
C14 N2 Cu2 118.54(10) . . ?
C16 N2 Cu2 110.30(10) . . ?
C8 N1 C10 108.49(12) . . ?
C8 N1 C12 111.15(13) . . ?
C10 N1 C12 111.63(12) . . ?
C8 N1 Cu1 109.59(9) . . ?
C10 N1 Cu1 108.84(9) . . ?
C12 N1 Cu1 107.08(9) . . ?
C7 C2 C3 118.69(13) . . ?
C7 C2 C1 120.17(12) . . ?
C3 C2 C1 121.07(13) . . ?
C2 C3 C4 120.77(14) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C6 C7 C2 121.14(13) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
N1 C8 C9 113.66(13) . . ?
N1 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
O2 C1 O1 125.70(14) . . ?
O2 C1 C2 118.89(13) . . ?
O1 C1 C2 115.40(13) . . ?
C7 C6 C5 119.81(14) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
O9 C19 C18 110.49(14) . 2_665 ?
O9 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 2_665 . ?
O9 C19 H19B 109.6 . . ?
C18 C19 H19B 109.6 2_665 . ?
H19A C19 H19B 108.1 . . ?
N1 C10 C11 112.69(12) . . ?
N1 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C5 C4 C3 119.85(13) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
N2 C14 C15 117.08(16) . . ?
N2 C14 H14A 108.0 . . ?
C15 C14 H14A 108.0 . . ?
N2 C14 H14B 108.0 . . ?
C15 C14 H14B 108.0 . . ?
H14A C14 H14B 107.3 . . ?
O4 C9 C8 113.61(14) . . ?
O4 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
O4 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O3 C5 C4 123.47(14) . . ?
O3 C5 C6 116.82(15) . . ?
C4 C5 C6 119.71(14) . . ?
O5 C11 C10 107.71(13) . . ?
O5 C11 H11A 110.2 . . ?
C10 C11 H11A 110.2 . . ?
O5 C11 H11B 110.2 . . ?
C10 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
N2 C18 C19 109.78(14) . 2_665 ?
N2 C18 H18A 109.7 . . ?
C19 C18 H18A 109.7 2_665 . ?
N2 C18 H18B 109.7 . . ?
C19 C18 H18B 109.7 2_665 . ?
H18A C18 H18B 108.2 . . ?
O8 C17 C16 111.24(14) . . ?
O8 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
O8 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C17 C16 N2 114.02(14) . . ?
C17 C16 H16A 108.7 . . ?
N2 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
N2 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
O7 C15 C14 115.70(17) . . ?
O7 C15 H15A 108.4 . . ?
C14 C15 H15A 108.4 . . ?
O7 C15 H15B 108.4 . . ?
C14 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
O6 C13 C12 107.43(12) . 2_666 ?
O6 C13 H13A 110.2 . . ?
C12 C13 H13A 110.2 2_666 . ?
O6 C13 H13B 110.2 . . ?
C12 C13 H13B 110.2 2_666 . ?
H13A C13 H13B 108.5 . . ?
N1 C12 C13 110.86(12) . 2_666 ?
N1 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 2_666 . ?
N1 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 2_666 . ?
H12A C12 H12B 108.1 . . ?

_refine_diff_density_max         0.628
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_complex4
_database_code_depnum_ccdc_archive 'CCDC 1531879'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H42 Cu2 N2 O12'
_chemical_formula_weight         701.69

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.5702(5)
_cell_length_b                   26.9513(17)
_cell_length_c                   8.0232(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.061(2)
_cell_angle_gamma                90
_cell_volume                     1527.60(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      25.50

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   0.700
_exptl_transmission_factor_max   0.792
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.455
_shelx_estimated_absorpt_T_min   0.669
_shelx_estimated_absorpt_T_max   0.801
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_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 APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16092
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.824
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2686
_reflns_number_gt                2382
_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.7101P] 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         2686
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.174
_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 0.3408(4) 0.36317(9) 0.2467(3) 0.0272(6) Uani 1 1 d . . . . .
C2 C 0.1743(4) 0.32934(9) 0.1620(3) 0.0262(6) Uani 1 1 d . . . . .
C3 C 0.0165(4) 0.33224(10) 0.2093(4) 0.0333(6) Uani 1 1 d . . . . .
H3 H 0.009104 0.357231 0.289995 0.040 Uiso 1 1 calc R U . . .
C4 C -0.1314(4) 0.29887(11) 0.1397(4) 0.0440(7) Uani 1 1 d . . . . .
H4 H -0.238733 0.300632 0.174289 0.053 Uiso 1 1 calc R U . . .
C5 C -0.1221(5) 0.26295(11) 0.0195(4) 0.0486(8) Uani 1 1 d . . . . .
H5 H -0.222868 0.239955 -0.028013 0.058 Uiso 1 1 calc R U . . .
C6 C 0.0327(5) 0.26062(11) -0.0308(4) 0.0461(8) Uani 1 1 d . . . . .
H6 H 0.037554 0.236371 -0.115001 0.055 Uiso 1 1 calc R U . . .
C7 C 0.1818(4) 0.29333(10) 0.0401(4) 0.0352(6) Uani 1 1 d . . . . .
H7 H 0.289338 0.291240 0.005759 0.042 Uiso 1 1 calc R U . . .
C8 C 0.3126(4) 0.50954(10) 0.1735(3) 0.0308(6) Uani 1 1 d . . . . .
H8A H 0.210857 0.487077 0.100253 0.037 Uiso 1 1 calc R U . . .
H8B H 0.427153 0.503372 0.144287 0.037 Uiso 1 1 calc R U . . .
C9 C 0.2506(4) 0.56340(10) 0.1356(4) 0.0331(6) Uani 1 1 d . . . . .
H9A H 0.253350 0.573134 0.017543 0.040 Uiso 1 1 calc R U . . .
H9B H 0.118986 0.566939 0.131526 0.040 Uiso 1 1 calc R U . . .
C10 C 0.5202(4) 0.62141(10) 0.2157(4) 0.0330(6) Uani 1 1 d . . . . .
H10A H 0.596596 0.644626 0.309609 0.040 Uiso 1 1 calc R U . . .
H10B H 0.453831 0.641048 0.106852 0.040 Uiso 1 1 calc R U . . .
C11 C 0.6503(4) 0.58489(11) 0.1761(4) 0.0376(7) Uani 1 1 d . . . . .
H11A H 0.578251 0.563921 0.072679 0.045 Uiso 1 1 calc R U . . .
H11B H 0.750056 0.602684 0.147108 0.045 Uiso 1 1 calc R U . . .
C12 C 0.2669(4) 0.63617(10) 0.3245(4) 0.0343(6) Uani 1 1 d . . . . .
H12A H 0.185469 0.653082 0.214064 0.041 Uiso 1 1 calc R U . . .
H12B H 0.355718 0.661130 0.400218 0.041 Uiso 1 1 calc R U . . .
C13 C 0.1439(4) 0.61700(13) 0.4227(4) 0.0438(8) Uani 1 1 d . . . . .
H13A H 0.082196 0.645575 0.457062 0.053 Uiso 1 1 calc R U . . .
H13B H 0.042883 0.595980 0.340258 0.053 Uiso 1 1 calc R U . . .
N1 N 0.3775(3) 0.59690(7) 0.2761(3) 0.0251(5) Uani 1 1 d . . . . .
O1 O 0.3214(3) 0.39466(6) 0.3560(3) 0.0339(4) Uani 1 1 d . . . . .
O2 O 0.4838(3) 0.35717(8) 0.2074(3) 0.0429(5) Uani 1 1 d . . . . .
O1W O 0.9501(3) 0.48117(8) 0.2835(3) 0.0420(5) Uani 1 1 d G . . . .
H1WA H 1.071512 0.485707 0.334209 0.063 Uiso 1 1 d G U . . .
H1WB H 0.916242 0.455702 0.331687 0.063 Uiso 1 1 d G U . . .
O3 O 0.3518(3) 0.50102(6) 0.3574(2) 0.0268(4) Uani 1 1 d . . . . .
O4 O 0.7327(3) 0.55515(8) 0.3298(3) 0.0403(5) Uani 1 1 d . . . . .
O5 O 0.2422(3) 0.58914(7) 0.5778(3) 0.0389(5) Uani 1 1 d . . . . .
H5A H 0.322147 0.607358 0.652460 0.058 Uiso 1 1 calc R U . . .
Cu1 Cu 0.48586(4) 0.44611(2) 0.50501(4) 0.02325(13) Uani 1 1 d . . . . .
H4A H 0.791(5) 0.5353(13) 0.309(5) 0.049(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
C1 O2 1.242(3) . ?
C1 O1 1.266(3) . ?
C1 C2 1.505(4) . ?
C2 C3 1.379(4) . ?
C2 C7 1.393(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.371(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O3 1.416(3) . ?
C8 C9 1.522(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.494(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N1 1.488(3) . ?
C10 C11 1.505(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O4 1.414(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N1 1.485(3) . ?
C12 C13 1.511(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O5 1.414(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
N1 Cu1 2.048(2) 3_666 ?
O1 Cu1 1.9579(17) . ?
O1W H1WA 0.8700 . ?
O1W H1WB 0.8701 . ?
O3 Cu1 1.9386(17) . ?
O3 Cu1 1.9451(17) 3_666 ?
O4 H4A 0.75(3) . ?
O5 H5A 0.8400 . ?
Cu1 Cu1 2.9157(6) 3_666 ?

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
O2 C1 O1 126.3(2) . . ?
O2 C1 C2 118.1(2) . . ?
O1 C1 C2 115.6(2) . . ?
C3 C2 C7 119.4(2) . . ?
C3 C2 C1 120.6(2) . . ?
C7 C2 C1 120.0(2) . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
O3 C8 C9 107.3(2) . . ?
O3 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O3 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
N1 C9 C8 110.9(2) . . ?
N1 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.0 . . ?
N1 C10 C11 112.7(2) . . ?
N1 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
O4 C11 C10 107.7(2) . . ?
O4 C11 H11A 110.2 . . ?
C10 C11 H11A 110.2 . . ?
O4 C11 H11B 110.2 . . ?
C10 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
N1 C12 C13 113.8(2) . . ?
N1 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N1 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
O5 C13 C12 114.4(2) . . ?
O5 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
O5 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C12 N1 C10 108.2(2) . . ?
C12 N1 C9 111.0(2) . . ?
C10 N1 C9 111.6(2) . . ?
C12 N1 Cu1 109.74(16) . 3_666 ?
C10 N1 Cu1 109.17(15) . 3_666 ?
C9 N1 Cu1 107.14(15) . 3_666 ?
C1 O1 Cu1 133.73(18) . . ?
H1WA O1W H1WB 109.5 . . ?
C8 O3 Cu1 128.91(16) . . ?
C8 O3 Cu1 109.00(14) . 3_666 ?
Cu1 O3 Cu1 97.31(8) . 3_666 ?
C11 O4 H4A 109(3) . . ?
C13 O5 H5A 109.5 . . ?
O3 Cu1 O3 82.69(8) . 3_666 ?
O3 Cu1 O1 95.12(8) . . ?
O3 Cu1 O1 177.22(8) 3_666 . ?
O3 Cu1 N1 161.49(8) . 3_666 ?
O3 Cu1 N1 84.64(8) 3_666 3_666 ?
O1 Cu1 N1 97.88(8) . 3_666 ?
O3 Cu1 Cu1 41.43(5) . 3_666 ?
O3 Cu1 Cu1 41.26(5) 3_666 3_666 ?
O1 Cu1 Cu1 136.52(6) . 3_666 ?
N1 Cu1 Cu1 124.63(6) 3_666 3_666 ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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_sg5
_database_code_depnum_ccdc_archive 'CCDC 1527824'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H48 Cu N2 O10'
_chemical_formula_sum            'C30 H48 Cu N2 O10'
_chemical_formula_weight         660.24

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   P21/n

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

_cell_length_a                   7.3376(14)
_cell_length_b                   21.415(4)
_cell_length_c                   10.712(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.900(19)
_cell_angle_gamma                90
_cell_volume                     1634.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      25.50

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             702
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8229
_exptl_absorpt_correction_T_max  0.8867
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(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 APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6445
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_sigmaI/netI    0.1162
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2833
_reflns_number_gt                1595
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  ?

_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)+(0.1713P)²+0.5330P] 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         2833
_refine_ls_number_parameters     204
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.2335
_refine_ls_wR_factor_gt          0.2066
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.085
_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 0.5000 0.5000 0.0000 0.0489(6) Uani 1 2 d SD . .
O2 O 0.6831(8) 0.5428(3) 0.1553(6) 0.0656(17) Uani 1 1 d D . .
O4 O 0.5689(8) 0.6378(3) 0.2652(7) 0.080(2) Uani 1 1 d . . .
O3 O 0.2605(9) 0.6176(3) 0.2234(7) 0.0740(19) Uani 1 1 d . . .
N1 N 0.4142(9) 0.4315(3) 0.1052(7) 0.0544(18) Uani 1 1 d . . .
O1 O 0.7331(8) 0.4279(3) 0.0013(6) 0.0667(17) Uani 1 1 d D . .
C9 C 0.3922(11) 0.6809(4) 0.4043(9) 0.057(2) Uani 1 1 d . . .
C8 C 0.4062(13) 0.6431(4) 0.2885(9) 0.063(2) Uani 1 1 d . . .
O5 O 0.7108(10) 0.7137(5) 0.4477(10) 0.112(3) Uani 1 1 d . . .
H5 H 0.6954 0.7084 0.3701 0.169 Uiso 1 1 calc R . .
C14 C 0.5394(14) 0.7145(5) 0.4785(10) 0.074(3) Uani 1 1 d . . .
C13 C 0.5236(16) 0.7469(5) 0.5855(9) 0.079(3) Uani 1 1 d . . .
H13 H 0.6251 0.7691 0.6340 0.095 Uiso 1 1 calc R . .
C2 C 0.5881(13) 0.3969(5) 0.1698(10) 0.071(3) Uani 1 1 d . . .
H2A H 0.6637 0.4231 0.2364 0.085 Uiso 1 1 calc R . .
H2B H 0.5534 0.3599 0.2109 0.085 Uiso 1 1 calc R . .
C12 C 0.3560(17) 0.7461(5) 0.6195(10) 0.079(3) Uani 1 1 d . . .
H12 H 0.3455 0.7667 0.6939 0.094 Uiso 1 1 calc R . .
C10 C 0.2191(13) 0.6832(4) 0.4401(9) 0.067(2) Uani 1 1 d . . .
H10 H 0.1150 0.6625 0.3909 0.080 Uiso 1 1 calc R . .
C11 C 0.2044(15) 0.7161(6) 0.5474(11) 0.082(3) Uani 1 1 d . . .
H11 H 0.0902 0.7176 0.5707 0.098 Uiso 1 1 calc R . .
C7 C 0.8189(11) 0.5721(5) 0.0983(10) 0.074(3) Uani 1 1 d D . .
H7A H 0.8978 0.5405 0.0729 0.088 Uiso 1 1 calc R . .
H7B H 0.8984 0.5994 0.1605 0.088 Uiso 1 1 calc R . .
C1 C 0.7023(13) 0.3780(5) 0.0786(11) 0.076(3) Uani 1 1 d D . .
H1A H 0.8224 0.3621 0.1268 0.091 Uiso 1 1 calc R . .
H1B H 0.6384 0.3447 0.0240 0.091 Uiso 1 1 calc R . .
C4 C 0.3235(13) 0.4610(4) 0.2021(9) 0.065(2) Uani 1 1 d . . .
H4A H 0.2094 0.4818 0.1564 0.078 Uiso 1 1 calc R . .
H4B H 0.4073 0.4927 0.2484 0.078 Uiso 1 1 calc R . .
C3 C 0.2769(12) 0.3917(4) 0.0148(10) 0.068(3) Uani 1 1 d . . .
H3A H 0.3416 0.3566 -0.0122 0.082 Uiso 1 1 calc R . .
H3B H 0.1851 0.3754 0.0581 0.082 Uiso 1 1 calc R . .
C5 C 0.2738(18) 0.4157(6) 0.3004(12) 0.096(4) Uani 1 1 d . . .
H5A H 0.3886 0.4010 0.3581 0.115 Uiso 1 1 calc R . .
H5B H 0.2087 0.3798 0.2554 0.115 Uiso 1 1 calc R . .
C6 C 0.148(2) 0.4469(7) 0.3804(15) 0.126(5) Uani 1 1 d D . .
H6A H 0.0454 0.4687 0.3231 0.151 Uiso 1 1 calc R . .
H6B H 0.0950 0.4149 0.4251 0.151 Uiso 1 1 calc R . .
C6A C 0.254(3) 0.4905(11) 0.473(2) 0.232(15) Uani 1 1 d D . .
H0AA H 0.3359 0.4679 0.5416 0.348 Uiso 1 1 calc R . .
H0AB H 0.1692 0.5156 0.5075 0.348 Uiso 1 1 calc R . .
H0AC H 0.3274 0.5170 0.4318 0.348 Uiso 1 1 calc R . .
H2 H 0.689(10) 0.558(5) 0.230(5) 0.348 Uiso 1 1 d D . .
H1 H 0.805(12) 0.416(3) -0.047(8) 0.348 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 2.040(7) 3_665 ?
Cu1 N1 2.040(7) . ?
Cu1 O2 2.083(6) . ?
Cu1 O2 2.083(6) 3_665 ?
Cu1 O1 2.302(6) 3_665 ?
Cu1 O1 2.302(6) . ?
O2 C7 1.432(10) . ?
O4 C8 1.282(10) . ?
O3 C8 1.252(11) . ?
N1 C3 1.487(11) . ?
N1 C2 1.494(11) . ?
N1 C4 1.501(10) . ?
O1 C1 1.403(11) . ?
C9 C14 1.379(13) . ?
C9 C10 1.413(12) . ?
C9 C8 1.506(12) . ?
O5 C14 1.375(12) . ?
C14 C13 1.368(14) . ?
C13 C12 1.364(14) . ?
C2 C1 1.488(13) . ?
C12 C11 1.355(14) . ?
C10 C11 1.374(14) . ?
C7 C3 1.468(14) 3_665 ?
C4 C5 1.538(14) . ?
C3 C7 1.468(14) 3_665 ?
C5 C6 1.552(15) . ?
C6 C6A 1.447(17) . ?

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 180.000(1) 3_665 . ?
N1 Cu1 O2 84.2(3) 3_665 . ?
N1 Cu1 O2 95.8(3) . . ?
N1 Cu1 O2 95.8(3) 3_665 3_665 ?
N1 Cu1 O2 84.2(3) . 3_665 ?
O2 Cu1 O2 180.0(3) . 3_665 ?
N1 Cu1 O1 80.9(2) 3_665 3_665 ?
N1 Cu1 O1 99.1(2) . 3_665 ?
O2 Cu1 O1 92.6(2) . 3_665 ?
O2 Cu1 O1 87.4(2) 3_665 3_665 ?
N1 Cu1 O1 99.1(2) 3_665 . ?
N1 Cu1 O1 80.9(2) . . ?
O2 Cu1 O1 87.4(2) . . ?
O2 Cu1 O1 92.6(2) 3_665 . ?
O1 Cu1 O1 180.000(1) 3_665 . ?
C7 O2 Cu1 103.5(5) . . ?
C3 N1 C2 112.8(7) . . ?
C3 N1 C4 110.3(6) . . ?
C2 N1 C4 111.1(7) . . ?
C3 N1 Cu1 107.7(5) . . ?
C2 N1 Cu1 105.7(5) . . ?
C4 N1 Cu1 109.1(5) . . ?
C1 O1 Cu1 106.8(5) . . ?
C14 C9 C10 117.1(9) . . ?
C14 C9 C8 123.8(9) . . ?
C10 C9 C8 119.1(8) . . ?
O3 C8 O4 124.4(9) . . ?
O3 C8 C9 118.3(8) . . ?
O4 C8 C9 117.3(8) . . ?
C13 C14 O5 118.2(10) . . ?
C13 C14 C9 122.4(11) . . ?
O5 C14 C9 119.3(10) . . ?
C12 C13 C14 118.7(10) . . ?
C1 C2 N1 112.5(8) . . ?
C11 C12 C13 121.5(10) . . ?
C11 C10 C9 120.1(10) . . ?
C12 C11 C10 120.1(10) . . ?
O2 C7 C3 109.8(7) . 3_665 ?
O1 C1 C2 112.2(8) . . ?
N1 C4 C5 115.2(8) . . ?
C7 C3 N1 110.4(7) 3_665 . ?
C4 C5 C6 112.2(10) . . ?
C6A C6 C5 111.4(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 O2 C7 -26.5(5) 3_665 . . . ?
N1 Cu1 O2 C7 153.5(5) . . . . ?
O2 Cu1 O2 C7 -143(100) 3_665 . . . ?
O1 Cu1 O2 C7 -107.1(5) 3_665 . . . ?
O1 Cu1 O2 C7 72.9(5) . . . . ?
N1 Cu1 N1 C3 -17(100) 3_665 . . . ?
O2 Cu1 N1 C3 -179.7(5) . . . . ?
O2 Cu1 N1 C3 0.3(5) 3_665 . . . ?
O1 Cu1 N1 C3 86.7(5) 3_665 . . . ?
O1 Cu1 N1 C3 -93.3(5) . . . . ?
N1 Cu1 N1 C2 104(100) 3_665 . . . ?
O2 Cu1 N1 C2 -58.9(6) . . . . ?
O2 Cu1 N1 C2 121.1(6) 3_665 . . . ?
O1 Cu1 N1 C2 -152.5(5) 3_665 . . . ?
O1 Cu1 N1 C2 27.5(5) . . . . ?
N1 Cu1 N1 C4 -136(100) 3_665 . . . ?
O2 Cu1 N1 C4 60.6(5) . . . . ?
O2 Cu1 N1 C4 -119.4(5) 3_665 . . . ?
O1 Cu1 N1 C4 -33.0(5) 3_665 . . . ?
O1 Cu1 N1 C4 147.0(5) . . . . ?
N1 Cu1 O1 C1 176.2(6) 3_665 . . . ?
N1 Cu1 O1 C1 -3.8(6) . . . . ?
O2 Cu1 O1 C1 92.5(6) . . . . ?
O2 Cu1 O1 C1 -87.5(6) 3_665 . . . ?
O1 Cu1 O1 C1 -11(100) 3_665 . . . ?
C14 C9 C8 O3 -175.6(9) . . . . ?
C10 C9 C8 O3 4.0(12) . . . . ?
C14 C9 C8 O4 6.1(13) . . . . ?
C10 C9 C8 O4 -174.3(8) . . . . ?
C10 C9 C14 C13 2.4(14) . . . . ?
C8 C9 C14 C13 -178.0(9) . . . . ?
C10 C9 C14 O5 180.0(9) . . . . ?
C8 C9 C14 O5 -0.5(15) . . . . ?
O5 C14 C13 C12 -177.7(10) . . . . ?
C9 C14 C13 C12 -0.2(16) . . . . ?
C3 N1 C2 C1 67.1(10) . . . . ?
C4 N1 C2 C1 -168.4(8) . . . . ?
Cu1 N1 C2 C1 -50.3(9) . . . . ?
C14 C13 C12 C11 -2.5(16) . . . . ?
C14 C9 C10 C11 -2.2(13) . . . . ?
C8 C9 C10 C11 178.1(9) . . . . ?
C13 C12 C11 C10 2.6(17) . . . . ?
C9 C10 C11 C12 -0.2(15) . . . . ?
Cu1 O2 C7 C3 49.4(8) . . . 3_665 ?
Cu1 O1 C1 C2 -22.0(9) . . . . ?
N1 C2 C1 O1 49.6(11) . . . . ?
C3 N1 C4 C5 69.4(11) . . . . ?
C2 N1 C4 C5 -56.5(11) . . . . ?
Cu1 N1 C4 C5 -172.5(7) . . . . ?
C2 N1 C3 C7 -143.6(8) . . . 3_665 ?
C4 N1 C3 C7 91.5(9) . . . 3_665 ?
Cu1 N1 C3 C7 -27.4(8) . . . 3_665 ?
N1 C4 C5 C6 -169.3(10) . . . . ?
C4 C5 C6 C6A -73.1(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.951
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.117
####################################################################### 
# 
# 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_complex11
_database_code_depnum_ccdc_archive 'CCDC 1527826'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H46 Cu2 N6 O12'
_chemical_formula_weight         977.95

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'

_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                   25.0426(14)
_cell_length_b                   10.0519(5)
_cell_length_c                   23.0481(13)
_cell_angle_alpha                90
_cell_angle_beta                 119.402(2)
_cell_angle_gamma                90
_cell_volume                     5054.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.13
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             2024
_exptl_transmission_factor_min   0.797
_exptl_transmission_factor_max   0.866
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.902
_shelx_estimated_absorpt_T_min   0.774
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_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 APEX'
_diffrn_measurement_method       /w-scans

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            72333
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.231
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_full        25.046
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4465
_reflns_number_gt                3875
_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+4.6840P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4465
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.13357(10) 0.4138(2) 0.18550(11) 0.0400(5) Uani 1 1 d . . . . .
C19 C 0.9517(3) 0.2260(9) 0.1518(3) 0.196(4) Uani 1 1 d . . . . .
H19A H 0.963454 0.284060 0.125780 0.294 Uiso 1 1 calc R U . . .
H19B H 0.984256 0.160973 0.176267 0.294 Uiso 1 1 calc R U . . .
H19C H 0.945306 0.279800 0.183349 0.294 Uiso 1 1 calc R U . . .
C20 C 0.8959(4) 0.1576(6) 0.1078(4) 0.138(2) Uani 1 1 d . . . . .
C4 C 0.22873(12) 0.4755(3) 0.28081(14) 0.0600(7) Uani 1 1 d . . . . .
H4 H 0.260352 0.539085 0.303472 0.072 Uiso 1 1 calc R U . . .
C5 C 0.23231(12) 0.3528(3) 0.30937(13) 0.0517(6) Uani 1 1 d . . . . .
C8 C 0.28759(15) 0.2144(3) 0.40548(15) 0.0721(9) Uani 1 1 d . . . . .
H8A H 0.288442 0.137723 0.379712 0.108 Uiso 1 1 calc R U . . .
H8B H 0.252193 0.207171 0.412591 0.108 Uiso 1 1 calc R U . . .
H8C H 0.325355 0.216378 0.448632 0.108 Uiso 1 1 calc R U . . .
C6 C 0.18650(12) 0.2606(3) 0.27681(13) 0.0561(7) Uani 1 1 d . . . . .
H6 H 0.188421 0.176573 0.296583 0.067 Uiso 1 1 calc R U . . .
C7 C 0.13744(12) 0.2917(3) 0.21478(13) 0.0516(6) Uani 1 1 d . . . . .
H7 H 0.105951 0.227878 0.192061 0.062 Uiso 1 1 calc R U . . .
C1 C 0.08231(10) 0.4455(2) 0.11747(11) 0.0380(5) Uani 1 1 d . . . . .
C9 C 0.07443(10) 0.4355(2) -0.03963(11) 0.0382(5) Uani 1 1 d . . . . .
C10 C 0.12076(11) 0.3958(2) -0.05916(12) 0.0402(5) Uani 1 1 d . . . . .
C12 C 0.20901(14) 0.4484(3) -0.07019(17) 0.0658(8) Uani 1 1 d . . . . .
H12 H 0.238532 0.511201 -0.067345 0.079 Uiso 1 1 calc R U . . .
C13 C 0.21102(12) 0.3195(3) -0.08889(14) 0.0538(7) Uani 1 1 d . . . . .
C16 C 0.26312(19) 0.1608(4) -0.1200(2) 0.0939(12) Uani 1 1 d . . . . .
H16A H 0.228300 0.142033 -0.164158 0.141 Uiso 1 1 calc R U . . .
H16B H 0.263118 0.097572 -0.087630 0.141 Uiso 1 1 calc R U . . .
H16C H 0.301406 0.151956 -0.121474 0.141 Uiso 1 1 calc R U . . .
C14 C 0.16847(13) 0.2283(3) -0.09339(15) 0.0588(7) Uani 1 1 d . . . . .
H14 H 0.169679 0.139397 -0.106695 0.071 Uiso 1 1 calc R U . . .
C15 C 0.12366(13) 0.2675(3) -0.07827(15) 0.0538(7) Uani 1 1 d . . . . .
H15 H 0.094240 0.204331 -0.081160 0.065 Uiso 1 1 calc R U . . .
C17 C -0.07536(11) 0.0696(3) -0.03762(14) 0.0510(6) Uani 1 1 d . . . . .
C18 C -0.10450(15) -0.0594(3) -0.0561(2) 0.0905(13) Uani 1 1 d . . . . .
H18A H -0.118516 -0.075958 -0.103289 0.136 Uiso 1 1 calc R U . . .
H18B H -0.139672 -0.061278 -0.048399 0.136 Uiso 1 1 calc R U . . .
H18C H -0.075067 -0.128263 -0.029032 0.136 Uiso 1 1 calc R U . . .
C11 C 0.16405(12) 0.4862(3) -0.05557(15) 0.0553(7) Uani 1 1 d . . . . .
H11 H 0.162714 0.575498 -0.042856 0.066 Uiso 1 1 calc R U . . .
C3 C 0.17968(11) 0.5061(3) 0.21978(12) 0.0510(6) Uani 1 1 d . . . . .
H3 H 0.177314 0.591321 0.200860 0.061 Uiso 1 1 calc R U . . .
N1 N -0.05303(10) 0.1696(2) -0.02368(11) 0.0510(5) Uani 1 1 d . . . . .
N2 N 0.8501(4) 0.1137(6) 0.0727(4) 0.206(3) Uani 1 1 d . . . . .
C21 C 0.9268(5) 0.8785(9) 0.2824(5) 0.200(4) Uani 1 1 d . . . . .
O5 O -0.07343(7) 0.44414(16) 0.02489(8) 0.0445(4) Uani 1 1 d . . . . .
N3 N 0.9191(9) 0.9784(10) 0.2740(8) 0.445(11) Uani 1 1 d . . . . .
O6 O 0.25813(10) 0.2916(2) -0.10089(13) 0.0793(7) Uani 1 1 d . . . . .
O2 O 0.04605(8) 0.35217(17) 0.08488(8) 0.0486(4) Uani 1 1 d . . . . .
O3 O 0.28291(9) 0.3332(2) 0.37003(10) 0.0709(6) Uani 1 1 d . . . . .
O4 O 0.04011(8) 0.34582(17) -0.03794(9) 0.0490(4) Uani 1 1 d . . . . .
O1 O 0.07948(8) 0.56216(17) 0.09686(8) 0.0458(4) Uani 1 1 d . . . . .
Cu1 Cu -0.01965(2) 0.37675(2) -0.00756(2) 0.03197(11) Uani 1 1 d . . . . .
C22 C 0.9402(4) 0.7468(9) 0.2902(4) 0.208(4) Uani 1 1 d . . . . .
H22A H 0.956030 0.720033 0.260598 0.312 Uiso 1 1 calc R U . . .
H22B H 0.903037 0.695938 0.279176 0.312 Uiso 1 1 calc R U . . .
H22C H 0.971271 0.729190 0.336529 0.312 Uiso 1 1 calc R 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
C2 C7 1.381(4) . ?
C2 C3 1.386(3) . ?
C2 C1 1.494(3) . ?
C19 C20 1.435(9) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N2 1.121(8) . ?
C4 C3 1.373(4) . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 O3 1.364(3) . ?
C5 C6 1.376(4) . ?
C8 O3 1.419(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C6 C7 1.388(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C1 O1 1.254(3) . ?
C1 O2 1.264(3) . ?
C9 O4 1.259(3) . ?
C9 O5 1.260(3) 5_565 ?
C9 C10 1.490(3) . ?
C10 C15 1.376(3) . ?
C10 C11 1.385(3) . ?
C12 C13 1.374(4) . ?
C12 C11 1.378(4) . ?
C12 H12 0.9500 . ?
C13 O6 1.366(3) . ?
C13 C14 1.371(4) . ?
C16 O6 1.411(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 N1 1.118(3) . ?
C17 C18 1.445(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C11 H11 0.9500 . ?
C3 H3 0.9500 . ?
N1 Cu1 2.206(2) . ?
C21 N3 1.023(9) . ?
C21 C22 1.356(10) . ?
O5 Cu1 1.9549(15) . ?
O2 Cu1 1.9660(16) . ?
O4 Cu1 1.9634(16) . ?
O1 Cu1 1.9573(16) 5_565 ?
Cu1 Cu1 2.6253(5) 5_565 ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C7 C2 C3 118.5(2) . . ?
C7 C2 C1 121.3(2) . . ?
C3 C2 C1 120.1(2) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C19 174.5(9) . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
O3 C5 C6 124.6(2) . . ?
O3 C5 C4 115.3(2) . . ?
C6 C5 C4 120.0(2) . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C6 C7 119.3(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 121.2(2) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
O1 C1 O2 125.3(2) . . ?
O1 C1 C2 117.1(2) . . ?
O2 C1 C2 117.5(2) . . ?
O4 C9 O5 125.1(2) . 5_565 ?
O4 C9 C10 117.6(2) . . ?
O5 C9 C10 117.4(2) 5_565 . ?
C15 C10 C11 118.1(2) . . ?
C15 C10 C9 121.2(2) . . ?
C11 C10 C9 120.6(2) . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
O6 C13 C14 124.3(3) . . ?
O6 C13 C12 115.2(3) . . ?
C14 C13 C12 120.5(2) . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 C15 119.1(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C10 C15 C14 121.6(2) . . ?
C10 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
N1 C17 C18 179.6(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C17 N1 Cu1 172.6(2) . . ?
N3 C21 C22 174(2) . . ?
C9 O5 Cu1 122.97(15) 5_565 . ?
C13 O6 C16 118.2(3) . . ?
C1 O2 Cu1 121.70(15) . . ?
C5 O3 C8 119.0(2) . . ?
C9 O4 Cu1 123.30(15) . . ?
C1 O1 Cu1 124.28(15) . 5_565 ?
O5 Cu1 O1 88.74(7) . 5_565 ?
O5 Cu1 O4 168.59(7) . . ?
O1 Cu1 O4 89.92(8) 5_565 . ?
O5 Cu1 O2 89.78(7) . . ?
O1 Cu1 O2 168.63(7) 5_565 . ?
O4 Cu1 O2 89.30(8) . . ?
O5 Cu1 N1 96.67(8) . . ?
O1 Cu1 N1 95.04(8) 5_565 . ?
O4 Cu1 N1 94.74(8) . . ?
O2 Cu1 N1 96.33(8) . . ?
O5 Cu1 Cu1 84.61(5) . 5_565 ?
O1 Cu1 Cu1 83.51(5) 5_565 5_565 ?
O4 Cu1 Cu1 83.98(5) . 5_565 ?
O2 Cu1 Cu1 85.13(5) . 5_565 ?
N1 Cu1 Cu1 178.05(6) . 5_565 ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C4 C5 O3 -179.9(3) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
O3 C5 C6 C7 -179.4(3) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
C3 C2 C7 C6 -0.6(4) . . . . ?
C1 C2 C7 C6 177.2(2) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C7 C2 C1 O1 174.3(2) . . . . ?
C3 C2 C1 O1 -7.9(3) . . . . ?
C7 C2 C1 O2 -7.0(3) . . . . ?
C3 C2 C1 O2 170.8(2) . . . . ?
O4 C9 C10 C15 3.6(4) . . . . ?
O5 C9 C10 C15 -177.7(2) 5_565 . . . ?
O4 C9 C10 C11 -173.4(2) . . . . ?
O5 C9 C10 C11 5.3(3) 5_565 . . . ?
C11 C12 C13 O6 -178.6(3) . . . . ?
C11 C12 C13 C14 0.3(5) . . . . ?
O6 C13 C14 C15 178.3(3) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C11 C10 C15 C14 0.2(4) . . . . ?
C9 C10 C15 C14 -176.8(2) . . . . ?
C13 C14 C15 C10 0.3(4) . . . . ?
C13 C12 C11 C10 0.3(5) . . . . ?
C15 C10 C11 C12 -0.5(4) . . . . ?
C9 C10 C11 C12 176.6(3) . . . . ?
C5 C4 C3 C2 -1.0(4) . . . . ?
C7 C2 C3 C4 1.4(4) . . . . ?
C1 C2 C3 C4 -176.5(2) . . . . ?
C14 C13 O6 C16 0.8(5) . . . . ?
C12 C13 O6 C16 179.7(3) . . . . ?
O1 C1 O2 Cu1 3.1(3) . . . . ?
C2 C1 O2 Cu1 -175.47(15) . . . . ?
C6 C5 O3 C8 -5.1(4) . . . . ?
C4 C5 O3 C8 174.6(3) . . . . ?
O5 C9 O4 Cu1 -2.9(3) 5_565 . . . ?
C10 C9 O4 Cu1 175.69(15) . . . . ?
O2 C1 O1 Cu1 -2.6(3) . . . 5_565 ?
C2 C1 O1 Cu1 175.98(14) . . . 5_565 ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_Complex8
_database_code_depnum_ccdc_archive 'CCDC 1527823'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H40 Cu N2 O10'
_chemical_formula_weight         604.14

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                   8.4412(3)
_cell_length_b                   10.9602(4)
_cell_length_c                   15.2987(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.7410(10)
_cell_angle_gamma                90
_cell_volume                     1413.77(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.50

_exptl_crystal_description       Needle
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             638
_exptl_transmission_factor_min   0.811
_exptl_transmission_factor_max   0.890
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.830
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_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 APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60722
_diffrn_reflns_av_unetI/netI     0.0090
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.287
_diffrn_reflns_theta_max         25.072
_diffrn_reflns_theta_full        25.072
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2507
_reflns_number_gt                2285
_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.6552P] 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         2507
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1452(3) -0.01264(19) -0.22615(15) 0.0476(5) Uani 1 1 d . . . . .
C2 C 0.0193(2) -0.00571(16) -0.29857(14) 0.0401(4) Uani 1 1 d . . . . .
C3 C -0.0690(3) 0.10020(19) -0.31233(14) 0.0480(5) Uani 1 1 d . . . . .
H3 H -0.052073 0.168007 -0.274349 0.058 Uiso 1 1 calc R U . . .
C4 C -0.1811(3) 0.1075(2) -0.38072(15) 0.0531(5) Uani 1 1 d . . . . .
H4 H -0.242519 0.179619 -0.388672 0.064 Uiso 1 1 calc R U . . .
C5 C -0.2048(2) 0.01069(18) -0.43786(14) 0.0443(5) Uani 1 1 d . . . . .
C6 C -0.1211(3) -0.09622(19) -0.42373(15) 0.0495(5) Uani 1 1 d . . . . .
H6 H -0.139300 -0.164358 -0.461263 0.059 Uiso 1 1 calc R U . . .
C7 C -0.0100(3) -0.10298(19) -0.35402(15) 0.0486(5) Uani 1 1 d . . . . .
H7 H 0.047332 -0.176695 -0.344278 0.058 Uiso 1 1 calc R U . . .
C8 C -0.3377(3) -0.0636(3) -0.56864(15) 0.0629(6) Uani 1 1 d . . . . .
H8A H -0.411325 -0.034900 -0.615680 0.094 Uiso 1 1 calc R U . . .
H8B H -0.382759 -0.135223 -0.540570 0.094 Uiso 1 1 calc R U . . .
H8C H -0.236407 -0.085728 -0.593093 0.094 Uiso 1 1 calc R U . . .
C9 C 0.4796(3) 0.2084(2) -0.10426(15) 0.0527(5) Uani 1 1 d . . . . .
H9A H 0.527835 0.264574 -0.059825 0.063 Uiso 1 1 calc R U . . .
H9B H 0.421823 0.257929 -0.149565 0.063 Uiso 1 1 calc R U . . .
C10 C 0.6071(3) 0.1355(2) -0.14525(15) 0.0577(6) Uani 1 1 d . . . . .
H10A H 0.561747 0.091045 -0.196935 0.069 Uiso 1 1 calc R U . . .
H10B H 0.690952 0.190807 -0.164938 0.069 Uiso 1 1 calc R U . . .
C11 C 0.7316(3) -0.0666(2) -0.12220(16) 0.0602(6) Uani 1 1 d . . . . .
H11A H 0.810064 -0.045410 -0.165822 0.072 Uiso 1 1 calc R U . . .
H11B H 0.785705 -0.118236 -0.076846 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6005(3) -0.1376(2) -0.16610(15) 0.0609(6) Uani 1 1 d . . . . .
H12A H 0.567043 -0.097276 -0.221867 0.073 Uiso 1 1 calc R U . . .
H12B H 0.639067 -0.220392 -0.179904 0.073 Uiso 1 1 calc R U . . .
C13 C 0.8126(3) 0.1025(3) -0.03091(17) 0.0668(7) Uani 1 1 d . . . . .
H13A H 0.782315 0.182440 -0.008363 0.100 Uiso 1 1 calc R U . . .
H13B H 0.901059 0.112300 -0.069531 0.100 Uiso 1 1 calc R U . . .
H13C H 0.845057 0.049049 0.018078 0.100 Uiso 1 1 calc R U . . .
N1 N 0.67579(19) 0.04774(16) -0.08060(10) 0.0413(4) Uani 1 1 d . . . . .
O1 O 0.37221(17) 0.12801(13) -0.06417(9) 0.0432(3) Uani 1 1 d . . . . .
O2 O 0.4682(2) -0.14714(15) -0.11234(10) 0.0540(4) Uani 1 1 d . . . . .
O3 O 0.2283(2) -0.10640(17) -0.22017(13) 0.0766(6) Uani 1 1 d . . . . .
O4 O 0.1585(2) 0.07792(18) -0.17601(12) 0.0730(5) Uani 1 1 d . . . . .
O5 O -0.3125(2) 0.03073(17) -0.50558(12) 0.0631(4) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.000000 0.000000 0.03256(13) Uani 1 2 d S . P . .
H1 H 0.312(3) 0.109(2) -0.0959(16) 0.049 Uiso 1 1 d . U . . .
H2 H 0.400(3) -0.136(2) -0.1400(16) 0.049 Uiso 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 O3 1.245(3) . ?
C1 O4 1.256(3) . ?
C1 C2 1.500(3) . ?
C2 C7 1.377(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 O5 1.363(3) . ?
C5 C6 1.380(3) . ?
C6 C7 1.388(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O5 1.423(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O1 1.424(3) . ?
C9 C10 1.501(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N1 1.478(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.487(4) . ?
C11 N1 1.492(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O2 1.423(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N1 1.479(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 Cu1 2.0423(15) . ?
O1 Cu1 1.9986(14) . ?
O1 H1 0.72(2) . ?
O2 Cu1 2.3628(16) . ?
O2 H2 0.71(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C1 O4 125.0(2) . . ?
O3 C1 C2 118.2(2) . . ?
O4 C1 C2 116.80(19) . . ?
C7 C2 C3 118.27(19) . . ?
C7 C2 C1 121.05(18) . . ?
C3 C2 C1 120.67(19) . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.55(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
O5 C5 C6 125.0(2) . . ?
O5 C5 C4 115.33(18) . . ?
C6 C5 C4 119.7(2) . . ?
C5 C6 C7 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 121.79(19) . . ?
C2 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
O5 C8 H8A 109.5 . . ?
O5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 C10 109.51(17) . . ?
O1 C9 H9A 109.8 . . ?
C10 C9 H9A 109.8 . . ?
O1 C9 H9B 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
N1 C10 C9 109.47(17) . . ?
N1 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
N1 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 N1 112.90(19) . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
N1 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O2 C12 C11 111.43(18) . . ?
O2 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
O2 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 N1 C13 110.59(18) . . ?
C10 N1 C11 112.52(17) . . ?
C13 N1 C11 107.78(18) . . ?
C10 N1 Cu1 107.30(13) . . ?
C13 N1 Cu1 111.45(13) . . ?
C11 N1 Cu1 107.20(13) . . ?
C9 O1 Cu1 107.84(12) . . ?
C9 O1 H1 110(2) . . ?
Cu1 O1 H1 118(2) . . ?
C12 O2 Cu1 107.77(13) . . ?
C12 O2 H2 106(2) . . ?
Cu1 O2 H2 112(2) . . ?
C5 O5 C8 118.09(19) . . ?
O1 Cu1 O1 180.0 . 3_655 ?
O1 Cu1 N1 85.08(6) . . ?
O1 Cu1 N1 94.92(6) 3_655 . ?
O1 Cu1 N1 94.92(6) . 3_655 ?
O1 Cu1 N1 85.08(6) 3_655 3_655 ?
N1 Cu1 N1 180.0 . 3_655 ?
O1 Cu1 O2 94.70(6) . . ?
O1 Cu1 O2 85.30(6) 3_655 . ?
N1 Cu1 O2 78.25(6) . . ?
N1 Cu1 O2 101.75(6) 3_655 . ?
O1 Cu1 O2 85.30(6) . 3_655 ?
O1 Cu1 O2 94.70(6) 3_655 3_655 ?
N1 Cu1 O2 101.75(6) . 3_655 ?
N1 Cu1 O2 78.25(6) 3_655 3_655 ?
O2 Cu1 O2 180.0 . 3_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C1 C2 C7 3.7(3) . . . . ?
O4 C1 C2 C7 -176.5(2) . . . . ?
O3 C1 C2 C3 -175.2(2) . . . . ?
O4 C1 C2 C3 4.6(3) . . . . ?
C7 C2 C3 C4 -1.0(3) . . . . ?
C1 C2 C3 C4 177.9(2) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C3 C4 C5 O5 -176.6(2) . . . . ?
C3 C4 C5 C6 3.2(3) . . . . ?
O5 C5 C6 C7 177.4(2) . . . . ?
C4 C5 C6 C7 -2.4(3) . . . . ?
C3 C2 C7 C6 1.8(3) . . . . ?
C1 C2 C7 C6 -177.1(2) . . . . ?
C5 C6 C7 C2 -0.1(3) . . . . ?
O1 C9 C10 N1 -50.6(3) . . . . ?
N1 C11 C12 O2 -45.6(3) . . . . ?
C9 C10 N1 C13 -90.6(2) . . . . ?
C9 C10 N1 C11 148.8(2) . . . . ?
C9 C10 N1 Cu1 31.1(2) . . . . ?
C12 C11 N1 C10 -64.2(2) . . . . ?
C12 C11 N1 C13 173.62(19) . . . . ?
C12 C11 N1 Cu1 53.5(2) . . . . ?
C10 C9 O1 Cu1 43.4(2) . . . . ?
C11 C12 O2 Cu1 15.6(2) . . . . ?
C6 C5 O5 C8 -2.2(3) . . . . ?
C4 C5 O5 C8 177.6(2) . . . . ?

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_complex10
_database_code_depnum_ccdc_archive 'CCDC 1527825'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H32 Cu2 O12'
_chemical_formula_weight         855.75

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'
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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.7710(9)
_cell_length_b                   11.7039(11)
_cell_length_c                   15.2527(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.111(5)
_cell_angle_gamma                90
_cell_volume                     1922.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      25.50

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             876
_exptl_transmission_factor_min   0.744
_exptl_transmission_factor_max   0.839
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.171
_shelx_estimated_absorpt_T_min   0.720
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_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 APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26448
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.193
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.047
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3393
_reflns_number_gt                3091
_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      'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+0.7717P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3393
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 0.33856(18) 0.68448(17) 0.59498(13) 0.0406(4) Uani 1 1 d . . . . .
C2 C 0.32454(19) 0.56547(18) 0.62625(13) 0.0431(4) Uani 1 1 d . . . . .
C3 C 0.2170(2) 0.5284(2) 0.66533(17) 0.0602(6) Uani 1 1 d . . . . .
H3 H 0.151038 0.578539 0.672754 0.072 Uiso 1 1 calc R U . . .
C4 C 0.2080(3) 0.4166(2) 0.6933(2) 0.0736(8) Uani 1 1 d . . . . .
H4 H 0.135952 0.391711 0.719950 0.088 Uiso 1 1 calc R U . . .
C5 C 0.3043(3) 0.3422(2) 0.68193(17) 0.0681(7) Uani 1 1 d . . . . .
H5 H 0.297371 0.266965 0.700740 0.082 Uiso 1 1 calc R U . . .
C6 C 0.4109(3) 0.3781(2) 0.64305(17) 0.0624(7) Uani 1 1 d . . . . .
H6 H 0.475842 0.327005 0.635089 0.075 Uiso 1 1 calc R U . . .
C7 C 0.4222(2) 0.49011(18) 0.61558(14) 0.0501(5) Uani 1 1 d . . . . .
H7 H 0.495223 0.514771 0.590028 0.060 Uiso 1 1 calc R U . . .
C8 C 0.27976(16) 1.05306(16) 0.54546(12) 0.0358(4) Uani 1 1 d . . . . .
C9 C 0.15135(17) 1.08423(17) 0.57045(13) 0.0393(4) Uani 1 1 d . . . . .
C10 C 0.0776(2) 1.0113(2) 0.61755(16) 0.0595(6) Uani 1 1 d . . . . .
H10 H 0.108172 0.940749 0.635815 0.071 Uiso 1 1 calc R U . . .
C11 C -0.0421(2) 1.0435(3) 0.6376(2) 0.0754(8) Uani 1 1 d . . . . .
H11 H -0.091456 0.994896 0.670276 0.090 Uiso 1 1 calc R U . . .
C12 C -0.0888(2) 1.1468(3) 0.60951(19) 0.0689(7) Uani 1 1 d . . . . .
H12 H -0.169927 1.167223 0.622144 0.083 Uiso 1 1 calc R U . . .
C13 C -0.0161(2) 1.2192(2) 0.5632(2) 0.0691(7) Uani 1 1 d . . . . .
H13 H -0.047604 1.289185 0.544313 0.083 Uiso 1 1 calc R U . . .
C14 C 0.1038(2) 1.1891(2) 0.54445(17) 0.0558(6) Uani 1 1 d . . . . .
H14 H 0.153553 1.239738 0.513928 0.067 Uiso 1 1 calc R U . . .
C15 C 0.41852(16) 0.96287(16) 0.34659(12) 0.0355(4) Uani 1 1 d . . . . .
C16 C 0.36270(16) 0.94156(18) 0.25777(12) 0.0385(4) Uani 1 1 d . . . . .
C17 C 0.3397(2) 1.0324(2) 0.20107(14) 0.0517(5) Uani 1 1 d . . . . .
H17 H 0.363443 1.106101 0.216949 0.062 Uiso 1 1 calc R U . . .
C18 C 0.2811(2) 1.0128(2) 0.12072(15) 0.0644(7) Uani 1 1 d . . . . .
H18 H 0.265966 1.073451 0.082642 0.077 Uiso 1 1 calc R U . . .
C19 C 0.2452(2) 0.9041(2) 0.09692(16) 0.0635(7) Uani 1 1 d . . . . .
H19 H 0.206050 0.891572 0.042919 0.076 Uiso 1 1 calc R U . . .
C20 C 0.2674(2) 0.8141(2) 0.15300(16) 0.0629(6) Uani 1 1 d . . . . .
H20 H 0.242261 0.740836 0.137191 0.075 Uiso 1 1 calc R U . . .
C21 C 0.3268(2) 0.8325(2) 0.23277(14) 0.0512(5) Uani 1 1 d . . . . .
H21 H 0.342957 0.771138 0.270019 0.061 Uiso 1 1 calc R U . . .
O1 O 0.43109(13) 0.71930(12) 0.55988(10) 0.0472(3) Uani 1 1 d . . . . .
O2 O 0.24049(16) 0.74879(14) 0.60775(14) 0.0715(5) Uani 1 1 d . . . . .
H2 H 0.254881 0.814228 0.591638 0.107 Uiso 1 1 calc R U . . .
O3 O 0.31467(12) 0.95024(11) 0.55429(9) 0.0420(3) Uani 1 1 d . . . . .
O4 O 0.65267(12) 0.86922(12) 0.48428(9) 0.0432(3) Uani 1 1 d . . . . .
O5 O 0.42328(13) 0.88013(11) 0.39931(9) 0.0420(3) Uani 1 1 d . . . . .
O6 O 0.54498(13) 0.93695(12) 0.63650(9) 0.0452(3) Uani 1 1 d . . . . .
Cu1 Cu 0.48212(2) 0.89335(2) 0.52084(2) 0.03162(9) 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 O1 1.211(2) . ?
C1 O2 1.315(2) . ?
C1 C2 1.481(3) . ?
C2 C3 1.383(3) . ?
C2 C7 1.385(3) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O4 1.255(2) 3_676 ?
C8 O3 1.267(2) . ?
C8 C9 1.487(3) . ?
C9 C10 1.377(3) . ?
C9 C14 1.385(3) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O5 1.259(2) . ?
C15 O6 1.262(2) 3_676 ?
C15 C16 1.492(3) . ?
C16 C21 1.385(3) . ?
C16 C17 1.390(3) . ?
C17 C18 1.387(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
O1 Cu1 2.1952(14) . ?
O2 H2 0.8200 . ?
O3 Cu1 1.9980(13) . ?
O4 Cu1 1.9507(13) . ?
O5 Cu1 1.9535(13) . ?
O6 Cu1 1.9454(13) . ?
Cu1 Cu1 2.6066(5) 3_676 ?

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 C1 O2 122.91(19) . . ?
O1 C1 C2 123.28(18) . . ?
O2 C1 C2 113.81(18) . . ?
C3 C2 C7 119.7(2) . . ?
C3 C2 C1 121.7(2) . . ?
C7 C2 C1 118.60(19) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 119.8(2) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
O4 C8 O3 123.62(17) 3_676 . ?
O4 C8 C9 117.61(17) 3_676 . ?
O3 C8 C9 118.77(17) . . ?
C10 C9 C14 118.97(19) . . ?
C10 C9 C8 122.03(18) . . ?
C14 C9 C8 118.99(18) . . ?
C9 C10 C11 119.7(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
O5 C15 O6 125.13(17) . 3_676 ?
O5 C15 C16 117.51(17) . . ?
O6 C15 C16 117.34(17) 3_676 . ?
C21 C16 C17 119.24(19) . . ?
C21 C16 C15 120.61(18) . . ?
C17 C16 C15 120.05(18) . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 120.5(2) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C1 O1 Cu1 130.14(13) . . ?
C1 O2 H2 109.5 . . ?
C8 O3 Cu1 123.84(12) . . ?
C8 O4 Cu1 123.65(12) 3_676 . ?
C15 O5 Cu1 123.61(12) . . ?
C15 O6 Cu1 122.05(12) 3_676 . ?
O6 Cu1 O4 89.09(6) . . ?
O6 Cu1 O5 169.13(6) . . ?
O4 Cu1 O5 90.42(6) . . ?
O6 Cu1 O3 88.91(6) . . ?
O4 Cu1 O3 168.81(5) . . ?
O5 Cu1 O3 89.48(6) . . ?
O6 Cu1 O1 94.70(6) . . ?
O4 Cu1 O1 100.68(6) . . ?
O5 Cu1 O1 96.06(6) . . ?
O3 Cu1 O1 90.46(5) . . ?
O6 Cu1 Cu1 85.38(4) . 3_676 ?
O4 Cu1 Cu1 85.67(4) . 3_676 ?
O5 Cu1 Cu1 83.75(4) . 3_676 ?
O3 Cu1 Cu1 83.19(4) . 3_676 ?
O1 Cu1 Cu1 173.65(4) . 3_676 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.4(2) . . . . ?
O2 C1 C2 C3 -0.2(3) . . . . ?
O1 C1 C2 C7 0.5(3) . . . . ?
O2 C1 C2 C7 179.7(2) . . . . ?
C7 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 C4 179.8(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C5 C6 C7 C2 -1.1(4) . . . . ?
C3 C2 C7 C6 0.8(3) . . . . ?
C1 C2 C7 C6 -179.1(2) . . . . ?
O4 C8 C9 C10 -168.4(2) 3_676 . . . ?
O3 C8 C9 C10 12.3(3) . . . . ?
O4 C8 C9 C14 12.6(3) 3_676 . . . ?
O3 C8 C9 C14 -166.7(2) . . . . ?
C14 C9 C10 C11 0.3(4) . . . . ?
C8 C9 C10 C11 -178.7(2) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C11 C12 C13 -1.4(5) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C9 1.4(4) . . . . ?
C10 C9 C14 C13 -1.6(4) . . . . ?
C8 C9 C14 C13 177.4(2) . . . . ?
O5 C15 C16 C21 -4.9(3) . . . . ?
O6 C15 C16 C21 176.42(18) 3_676 . . . ?
O5 C15 C16 C17 171.37(18) . . . . ?
O6 C15 C16 C17 -7.3(3) 3_676 . . . ?
C21 C16 C17 C18 0.2(3) . . . . ?
C15 C16 C17 C18 -176.2(2) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
C19 C20 C21 C16 1.2(4) . . . . ?
C17 C16 C21 C20 -0.9(3) . . . . ?
C15 C16 C21 C20 175.5(2) . . . . ?
O2 C1 O1 Cu1 8.2(3) . . . . ?
C2 C1 O1 Cu1 -172.77(13) . . . . ?
O4 C8 O3 Cu1 -1.0(3) 3_676 . . . ?
C9 C8 O3 Cu1 178.27(12) . . . . ?
O6 C15 O5 Cu1 2.9(3) 3_676 . . . ?
C16 C15 O5 Cu1 -175.59(11) . . . . ?

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.077

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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data_Complex7
_database_code_depnum_ccdc_archive 'CCDC 1527822'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H36 Cu N2 O8'
_chemical_formula_weight         544.09

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      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                   7.055(5)
_cell_length_b                   8.673(5)
_cell_length_c                   21.625(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.895(5)
_cell_angle_gamma                90
_cell_volume                     1321.5(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             574
_exptl_transmission_factor_min   0.802
_exptl_transmission_factor_max   0.862
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.874
_shelx_estimated_absorpt_T_min   0.792
_shelx_estimated_absorpt_T_max   0.866
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_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 APEX'
_diffrn_measurement_method       /w-scans

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52698
_diffrn_reflns_av_unetI/netI     0.0091
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.531
_diffrn_reflns_theta_max         25.072
_diffrn_reflns_theta_full        25.072
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2357
_reflns_number_gt                2238
_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.5097P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0275(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2357
_refine_ls_number_parameters     168
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2075(3) 0.8814(2) 0.37546(8) 0.0412(4) Uani 1 1 d . . . . .
C2 C -0.2719(3) 0.97702(19) 0.32014(9) 0.0430(4) Uani 1 1 d . . . . .
C3 C -0.1463(4) 1.0126(2) 0.27524(11) 0.0608(6) Uani 1 1 d . . . . .
H3 H -0.021606 0.977802 0.278994 0.073 Uiso 1 1 calc R U . . .
C4 C -0.2077(5) 1.1010(3) 0.22434(11) 0.0864(9) Uani 1 1 d . . . . .
H4 H -0.123143 1.125828 0.194263 0.104 Uiso 1 1 calc R U . . .
C5 C -0.3915(6) 1.1517(3) 0.21815(13) 0.0958(11) Uani 1 1 d . . . . .
H5 H -0.431755 1.209023 0.183587 0.115 Uiso 1 1 calc R U . . .
C6 C -0.5151(5) 1.1184(3) 0.26251(14) 0.0870(9) Uani 1 1 d . . . . .
H6 H -0.639445 1.154082 0.258467 0.104 Uiso 1 1 calc R U . . .
C7 C -0.4564(4) 1.0310(3) 0.31385(12) 0.0596(6) Uani 1 1 d . . . . .
H7 H -0.541440 1.008844 0.344108 0.071 Uiso 1 1 calc R U . . .
C8 C -0.1993(3) 0.7755(3) 0.55940(11) 0.0603(5) Uani 1 1 d D . . . .
H8A H -0.308755 0.795128 0.583614 0.072 Uiso 1 1 calc R U . . .
H8B H -0.157949 0.873018 0.542762 0.072 Uiso 1 1 calc R U . . .
C9 C -0.0430(3) 0.7084(3) 0.60032(10) 0.0568(5) Uani 1 1 d . . . . .
H9A H 0.005924 0.787666 0.628470 0.068 Uiso 1 1 calc R U . . .
H9B H -0.094593 0.626575 0.625000 0.068 Uiso 1 1 calc R U . . .
C10 C 0.2175(3) 0.7686(2) 0.53190(10) 0.0554(5) Uani 1 1 d . . . . .
H10A H 0.132731 0.854885 0.523429 0.067 Uiso 1 1 calc R U . . .
H10B H 0.325141 0.805194 0.557477 0.067 Uiso 1 1 calc R U . . .
C11 C 0.2842(3) 0.7060(2) 0.47266(10) 0.0496(5) Uani 1 1 d D . . . .
H11A H 0.334245 0.788679 0.448058 0.060 Uiso 1 1 calc R U . . .
H11B H 0.384541 0.631227 0.481058 0.060 Uiso 1 1 calc R U . . .
C12 C 0.2495(3) 0.5643(3) 0.60933(10) 0.0645(6) Uani 1 1 d . . . . .
H12A H 0.290808 0.633462 0.641960 0.097 Uiso 1 1 calc R U . . .
H12B H 0.357359 0.529509 0.587858 0.097 Uiso 1 1 calc R U . . .
H12C H 0.186824 0.477309 0.626636 0.097 Uiso 1 1 calc R U . . .
N1 N 0.1161(2) 0.64552(16) 0.56547(6) 0.0390(3) Uani 1 1 d . . . . .
O1 O -0.25140(17) 0.67446(15) 0.51008(6) 0.0451(3) Uani 1 1 d D . . . .
O2 O 0.12661(16) 0.63386(14) 0.43945(5) 0.0394(3) Uani 1 1 d D . . . .
O3 O -0.3273(2) 0.84438(19) 0.41243(7) 0.0656(4) Uani 1 1 d . . . . .
O4 O -0.0357(2) 0.8474(2) 0.38039(8) 0.0733(5) Uani 1 1 d . . . . .
Cu1 Cu 0.000000 0.500000 0.500000 0.02963(13) Uani 1 2 d DS . P . .
H1 H -0.289(2) 0.7371(17) 0.4802(6) 0.044 Uiso 1 1 d D U . . .
H2 H 0.071(2) 0.7054(16) 0.4174(7) 0.044 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O3 1.235(2) . ?
C1 O4 1.247(2) . ?
C1 C2 1.507(2) . ?
C2 C3 1.382(3) . ?
C2 C7 1.384(3) . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.360(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O1 1.414(3) . ?
C8 C9 1.496(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.487(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.490(3) . ?
C10 N1 1.493(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O2 1.436(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N1 1.480(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 Cu1 2.0374(14) . ?
O1 Cu1 2.3499(17) . ?
O1 H1 0.875(9) . ?
O2 Cu1 1.9946(13) . ?
O2 H2 0.865(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C1 O4 125.26(17) . . ?
O3 C1 C2 117.96(17) . . ?
O4 C1 C2 116.78(17) . . ?
C3 C2 C7 119.2(2) . . ?
C3 C2 C1 120.2(2) . . ?
C7 C2 C1 120.57(19) . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 120.3(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
O1 C8 C9 111.17(17) . . ?
O1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
O1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 C8 113.29(17) . . ?
N1 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 N1 109.73(16) . . ?
C11 C10 H10A 109.7 . . ?
N1 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
N1 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O2 C11 C10 108.56(15) . . ?
O2 C11 H11A 110.0 . . ?
C10 C11 H11A 110.0 . . ?
O2 C11 H11B 110.0 . . ?
C10 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C12 N1 C9 108.75(17) . . ?
C12 N1 C10 110.29(16) . . ?
C9 N1 C10 112.12(16) . . ?
C12 N1 Cu1 111.77(12) . . ?
C9 N1 Cu1 106.98(11) . . ?
C10 N1 Cu1 106.90(11) . . ?
C8 O1 Cu1 107.45(11) . . ?
C8 O1 H1 103.3(11) . . ?
Cu1 O1 H1 122.4(11) . . ?
C11 O2 Cu1 106.64(11) . . ?
C11 O2 H2 106.5(11) . . ?
Cu1 O2 H2 124.9(11) . . ?
O2 Cu1 O2 180.0 3_566 . ?
O2 Cu1 N1 94.71(6) 3_566 . ?
O2 Cu1 N1 85.29(6) . . ?
O2 Cu1 N1 85.29(6) 3_566 3_566 ?
O2 Cu1 N1 94.71(6) . 3_566 ?
N1 Cu1 N1 180.00(6) . 3_566 ?
O2 Cu1 O1 87.06(6) 3_566 . ?
O2 Cu1 O1 92.94(6) . . ?
N1 Cu1 O1 79.37(6) . . ?
N1 Cu1 O1 100.63(6) 3_566 . ?
O2 Cu1 O1 92.94(6) 3_566 3_566 ?
O2 Cu1 O1 87.06(6) . 3_566 ?
N1 Cu1 O1 100.63(6) . 3_566 ?
N1 Cu1 O1 79.37(6) 3_566 3_566 ?
O1 Cu1 O1 180.0 . 3_566 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C1 C2 C3 -175.60(19) . . . . ?
O4 C1 C2 C3 5.1(3) . . . . ?
O3 C1 C2 C7 4.9(3) . . . . ?
O4 C1 C2 C7 -174.4(2) . . . . ?
C7 C2 C3 C4 -0.5(3) . . . . ?
C1 C2 C3 C4 180.0(2) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C4 C5 C6 C7 -0.8(5) . . . . ?
C3 C2 C7 C6 0.9(3) . . . . ?
C1 C2 C7 C6 -179.6(2) . . . . ?
C5 C6 C7 C2 -0.2(4) . . . . ?
O1 C8 C9 N1 47.6(3) . . . . ?
N1 C10 C11 O2 51.7(2) . . . . ?
C8 C9 N1 C12 -172.60(18) . . . . ?
C8 C9 N1 C10 65.2(2) . . . . ?
C8 C9 N1 Cu1 -51.7(2) . . . . ?
C11 C10 N1 C12 92.76(19) . . . . ?
C11 C10 N1 C9 -145.89(17) . . . . ?
C11 C10 N1 Cu1 -28.95(19) . . . . ?
C9 C8 O1 Cu1 -19.0(2) . . . . ?
C10 C11 O2 Cu1 -47.37(17) . . . . ?

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.056

