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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1936224'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;CQE, Instituto Superior Tecnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2019-06-24 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H28 Cu0.50 N O7'
_chemical_formula_weight         366.15

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                   10.1856(14)
_cell_length_b                   16.187(2)
_cell_length_c                   11.0278(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.519(5)
_cell_angle_gamma                90
_cell_volume                     1817.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3827
_cell_measurement_theta_min      2.235
_cell_measurement_theta_max      27.157

_exptl_crystal_description       block
_exptl_crystal_colour            blue


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             782
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.666
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  0.955

_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)


_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40879
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_av_R_equivalents  0.1208
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.235
_diffrn_reflns_theta_max         27.157
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3827
_reflns_number_gt                2768
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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


_computing_data_collection       'BRUKER SMART (Bruker, 2005)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.2'
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1433P)²+1.4845P] 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         3827
_refine_ls_number_parameters     215
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0767
_refine_ls_wR_factor_ref         0.2347
_refine_ls_wR_factor_gt          0.2110
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.0000 0.0000 0.0344(3) Uani 1 2 d S . P . .
O1 O 0.6843(3) 0.1426(2) 0.0996(3) 0.0483(8) Uani 1 1 d . . . . .
O2 O 0.6858(3) 0.1493(2) -0.1008(3) 0.0508(8) Uani 1 1 d . . . . .
N1 N 1.1063(3) 0.0826(2) 0.1037(3) 0.0408(8) Uani 1 1 d . . . . .
O4 O 0.9421(3) 0.1214(2) -0.1004(3) 0.0491(8) Uani 1 1 d D . . . .
O3 O 0.1809(3) 0.3680(2) -0.0040(3) 0.0559(9) Uani 1 1 d . . . . .
H3O H 0.1684 0.3860 0.0642 0.084 Uiso 1 1 calc R U . . .
O5 O 1.1652(3) -0.0124(2) -0.0985(3) 0.0455(8) Uani 1 1 d D . . . .
C8 C 1.2479(5) 0.0577(3) -0.0737(5) 0.0506(12) Uani 1 1 d . . . . .
H8B H 1.2178 0.1045 -0.1219 0.061 Uiso 1 1 calc R U . . .
H8A H 1.3374 0.0452 -0.0954 0.061 Uiso 1 1 calc R U . . .
C9 C 1.2434(4) 0.0788(3) 0.0595(5) 0.0499(12) Uani 1 1 d . . . . .
H9B H 1.2922 0.0375 0.1058 0.060 Uiso 1 1 calc R U . . .
H9A H 1.2858 0.1318 0.0734 0.060 Uiso 1 1 calc R U . . .
C12 C 1.1045(5) 0.0554(3) 0.2341(4) 0.0469(11) Uani 1 1 d . . . . .
H12B H 1.1321 -0.0019 0.2378 0.056 Uiso 1 1 calc R U . . .
H12A H 1.0144 0.0576 0.2603 0.056 Uiso 1 1 calc R U . . .
C13 C 1.1895(5) 0.1044(3) 0.3248(4) 0.0496(11) Uani 1 1 d . . . . .
H13A H 1.2813 0.0986 0.3051 0.060 Uiso 1 1 calc R U . . .
H13B H 1.1667 0.1625 0.3200 0.060 Uiso 1 1 calc R U . . .
C14 C 1.1683(6) 0.0729(4) 0.4528(5) 0.0634(14) Uani 1 1 d . . . . .
H14B H 1.1772 0.0132 0.4536 0.076 Uiso 1 1 calc R U . . .
H14A H 1.0797 0.0862 0.4761 0.076 Uiso 1 1 calc R U . . .
C15 C 1.2655(8) 0.1100(6) 0.5449(6) 0.084(2) Uani 1 1 d . . . . .
H15C H 1.2542 0.0845 0.6225 0.126 Uiso 1 1 calc R U . . .
H15A H 1.2502 0.1683 0.5514 0.126 Uiso 1 1 calc R U . . .
H15B H 1.3535 0.1006 0.5189 0.126 Uiso 1 1 calc R U . . .
C10 C 1.0440(5) 0.1650(3) 0.0908(4) 0.0467(11) Uani 1 1 d . . . . .
H10B H 1.1030 0.2063 0.1251 0.056 Uiso 1 1 calc R U . . .
H10A H 0.9643 0.1658 0.1372 0.056 Uiso 1 1 calc R U . . .
C11 C 1.0102(5) 0.1879(3) -0.0388(5) 0.0499(11) Uani 1 1 d . . . . .
H11B H 0.9554 0.2369 -0.0403 0.060 Uiso 1 1 calc R U . . .
H11A H 1.0902 0.2006 -0.0809 0.060 Uiso 1 1 calc R U . . .
C5 C 0.2926(4) 0.3207(3) -0.0022(4) 0.0399(9) Uani 1 1 d . . . . .
C6 C 0.3355(4) 0.2876(3) -0.1106(4) 0.0417(10) Uani 1 1 d . . . . .
H6 H 0.2902 0.2984 -0.1832 0.050 Uiso 1 1 calc R U . . .
C7 C 0.4465(4) 0.2384(3) -0.1089(4) 0.0404(10) Uani 1 1 d . . . . .
H7 H 0.4756 0.2165 -0.1814 0.048 Uiso 1 1 calc R U . . .
C2 C 0.5157(4) 0.2209(3) -0.0015(4) 0.0363(9) Uani 1 1 d . . . . .
C1 C 0.6360(4) 0.1669(3) -0.0011(4) 0.0382(9) Uani 1 1 d . . . . .
C4 C 0.3607(5) 0.3052(3) 0.1049(4) 0.0465(11) Uani 1 1 d . . . . .
H4 H 0.3321 0.3283 0.1767 0.056 Uiso 1 1 calc R U . . .
C3 C 0.4713(4) 0.2555(3) 0.1065(4) 0.0423(10) Uani 1 1 d . . . . .
H3 H 0.5163 0.2450 0.1794 0.051 Uiso 1 1 calc R U . . .
O1W O 0.0518(6) 0.4242(4) -0.2069(5) 0.0940(15) Uiso 1 1 d . . . . .
O2W O 0.0796(6) 0.4282(4) 0.1993(5) 0.1012(16) Uiso 1 1 d . . . . .
H1W H 0.1031 0.4151 -0.1452 0.121 Uiso 1 1 d . U . . .
H2W H 0.0607 0.3822 -0.2541 0.121 Uiso 1 1 d . U . . .
H3W H 0.0509 0.4199 0.2711 0.121 Uiso 1 1 d . U . . .
H4W H 0.1189 0.4758 0.2033 0.121 Uiso 1 1 d . U . . .
H4O H 0.859(2) 0.138(3) -0.100(4) 0.049(14) Uiso 1 1 d D . . . .
H5O H 1.209(6) -0.061(2) -0.100(5) 0.067(18) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O5 2.037(3) . ?
Cu1 O5 2.037(3) 3_755 ?
Cu1 N1 2.050(4) . ?
Cu1 N1 2.050(4) 3_755 ?
Cu1 O4 2.324(4) 3_755 ?
Cu1 O4 2.324(4) . ?
O1 C1 1.266(5) . ?
O2 C1 1.255(5) . ?
N1 C10 1.481(6) . ?
N1 C9 1.493(5) . ?
N1 C12 1.505(6) . ?
O4 C11 1.440(6) . ?
O4 H4O 0.886(19) . ?
O3 C5 1.372(5) . ?
O3 H3O 0.8200 . ?
O5 C8 1.435(6) . ?
O5 H5O 0.900(19) . ?
C8 C9 1.511(7) . ?
C8 H8B 0.9700 . ?
C8 H8A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9A 0.9700 . ?
C12 C13 1.528(7) . ?
C12 H12B 0.9700 . ?
C12 H12A 0.9700 . ?
C13 C14 1.521(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.524(9) . ?
C14 H14B 0.9700 . ?
C14 H14A 0.9700 . ?
C15 H15C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C10 C11 1.508(7) . ?
C10 H10B 0.9700 . ?
C10 H10A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11A 0.9700 . ?
C5 C4 1.376(7) . ?
C5 C6 1.391(6) . ?
C6 C7 1.382(6) . ?
C6 H6 0.9300 . ?
C7 C2 1.391(6) . ?
C7 H7 0.9300 . ?
C2 C3 1.402(6) . ?
C2 C1 1.505(6) . ?
C4 C3 1.384(7) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
O1W H1W 0.859(6) . ?
O1W H2W 0.863(6) . ?
O2W H3W 0.861(5) . ?
O2W H4W 0.869(7) . ?

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 180.0 . 3_755 ?
O5 Cu1 N1 85.99(13) . . ?
O5 Cu1 N1 94.01(13) 3_755 . ?
O5 Cu1 N1 94.01(13) . 3_755 ?
O5 Cu1 N1 85.99(13) 3_755 3_755 ?
N1 Cu1 N1 180.0 . 3_755 ?
O5 Cu1 O4 88.15(12) . 3_755 ?
O5 Cu1 O4 91.85(12) 3_755 3_755 ?
N1 Cu1 O4 99.35(13) . 3_755 ?
N1 Cu1 O4 80.65(13) 3_755 3_755 ?
O5 Cu1 O4 91.85(12) . . ?
O5 Cu1 O4 88.15(12) 3_755 . ?
N1 Cu1 O4 80.65(13) . . ?
N1 Cu1 O4 99.35(13) 3_755 . ?
O4 Cu1 O4 180.0 3_755 . ?
C10 N1 C9 114.1(4) . . ?
C10 N1 C12 109.8(3) . . ?
C9 N1 C12 109.6(4) . . ?
C10 N1 Cu1 108.4(3) . . ?
C9 N1 Cu1 106.0(3) . . ?
C12 N1 Cu1 108.8(3) . . ?
C11 O4 Cu1 107.1(3) . . ?
C11 O4 H4O 103(4) . . ?
Cu1 O4 H4O 119(4) . . ?
C5 O3 H3O 109.5 . . ?
C8 O5 Cu1 108.0(3) . . ?
C8 O5 H5O 114(4) . . ?
Cu1 O5 H5O 121(4) . . ?
O5 C8 C9 109.3(4) . . ?
O5 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
O5 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
H8B C8 H8A 108.3 . . ?
N1 C9 C8 112.3(4) . . ?
N1 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
N1 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
H9B C9 H9A 107.9 . . ?
N1 C12 C13 116.9(4) . . ?
N1 C12 H12B 108.1 . . ?
C13 C12 H12B 108.1 . . ?
N1 C12 H12A 108.1 . . ?
C13 C12 H12A 108.1 . . ?
H12B C12 H12A 107.3 . . ?
C14 C13 C12 110.0(5) . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 C15 112.4(6) . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
H14B C14 H14A 107.9 . . ?
C14 C15 H15C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
H15C C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15C C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C10 C11 113.4(4) . . ?
N1 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
N1 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
H10B C10 H10A 107.7 . . ?
O4 C11 C10 111.0(4) . . ?
O4 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
O4 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
H11B C11 H11A 108.0 . . ?
O3 C5 C4 120.9(4) . . ?
O3 C5 C6 118.8(4) . . ?
C4 C5 C6 120.3(4) . . ?
C7 C6 C5 119.0(4) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C2 121.6(4) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
C7 C2 C3 118.3(4) . . ?
C7 C2 C1 121.0(4) . . ?
C3 C2 C1 120.7(4) . . ?
O2 C1 O1 122.8(4) . . ?
O2 C1 C2 118.5(4) . . ?
O1 C1 C2 118.7(3) . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
H1W O1W H2W 105.7(6) . . ?
H3W O2W H4W 104.9(6) . . ?

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 O5 C8 C9 39.8(5) . . . . ?
C10 N1 C9 C8 -88.6(5) . . . . ?
C12 N1 C9 C8 147.8(4) . . . . ?
Cu1 N1 C9 C8 30.6(5) . . . . ?
O5 C8 C9 N1 -48.4(6) . . . . ?
C10 N1 C12 C13 -67.3(5) . . . . ?
C9 N1 C12 C13 58.8(5) . . . . ?
Cu1 N1 C12 C13 174.3(3) . . . . ?
N1 C12 C13 C14 175.8(4) . . . . ?
C12 C13 C14 C15 171.2(5) . . . . ?
C9 N1 C10 C11 71.2(5) . . . . ?
C12 N1 C10 C11 -165.4(4) . . . . ?
Cu1 N1 C10 C11 -46.7(4) . . . . ?
Cu1 O4 C11 C10 -24.3(4) . . . . ?
N1 C10 C11 O4 48.3(5) . . . . ?
O3 C5 C6 C7 -178.7(4) . . . . ?
C4 C5 C6 C7 0.7(7) . . . . ?
C5 C6 C7 C2 0.4(7) . . . . ?
C6 C7 C2 C3 -0.9(7) . . . . ?
C6 C7 C2 C1 179.7(4) . . . . ?
C7 C2 C1 O2 11.8(6) . . . . ?
C3 C2 C1 O2 -167.5(4) . . . . ?
C7 C2 C1 O1 -169.6(4) . . . . ?
C3 C2 C1 O1 11.1(6) . . . . ?
O3 C5 C4 C3 178.2(4) . . . . ?
C6 C5 C4 C3 -1.1(7) . . . . ?
C5 C4 C3 C2 0.5(7) . . . . ?
C7 C2 C3 C4 0.5(7) . . . . ?
C1 C2 C3 C4 179.8(4) . . . . ?

_refine_diff_density_max         1.533
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.112

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1936225'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;CQE, Instituto Superior Tecnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2019-06-24 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H31 Cu N O6'
_chemical_formula_weight         481.03

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

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

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

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

_cell_length_a                   10.6013(6)
_cell_length_b                   25.1550(13)
_cell_length_c                   8.9311(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.342(2)
_cell_angle_gamma                90
_cell_volume                     2247.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14787
_cell_measurement_theta_min      2.549
_cell_measurement_theta_max      26.382

_exptl_crystal_description       block
_exptl_crystal_colour            blue


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             1012
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.011
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.960

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  0.960

_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)


_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14787
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.549
_diffrn_reflns_theta_max         26.382
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             4455
_reflns_number_gt                2782
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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


_computing_data_collection       'BRUKER SMART (Bruker, 2005)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.2'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+24.8780P] 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         4455
_refine_ls_number_parameters     284
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1572
_refine_ls_R_factor_gt           0.1015
_refine_ls_wR_factor_ref         0.2197
_refine_ls_wR_factor_gt          0.1928
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.93519(16) 0.05204(3) 0.97808(10) 0.0697(5) Uani 1 1 d . . . . .
O2 O 0.7621(5) 0.06087(18) 0.6154(6) 0.0412(13) Uani 1 1 d . . . . .
C10 C 0.8767(8) 0.2294(2) 0.4718(7) 0.0307(17) Uani 1 1 d . . . . .
C3 C 0.6592(8) 0.1713(3) 0.5073(7) 0.0352(18) Uani 1 1 d . . . . .
C15 C 0.9004(8) 0.1818(2) 0.5667(7) 0.0314(17) Uani 1 1 d . . . . .
N1 N 0.8397(7) 0.0829(2) 1.1214(7) 0.0424(17) Uani 1 1 d D . . . .
C9 C 0.7464(8) 0.2464(3) 0.3983(8) 0.0369(19) Uani 1 1 d . . . . .
H9 H 0.7313 0.2776 0.3348 0.044 Uiso 1 1 calc R U . . .
C2 C 0.7908(8) 0.1535(3) 0.5804(7) 0.0304(16) Uani 1 1 d . . . . .
O3 O 1.1039(10) 0.1058(3) 1.1328(7) 0.093(2) Uani 1 1 d D . . . .
O1 O 0.8829(6) 0.10917(19) 0.8238(5) 0.0514(17) Uani 1 1 d . . . . .
C14 C 1.0352(8) 0.1652(2) 0.6395(8) 0.0303(16) Uani 1 1 d . . . . .
H14 H 1.0533 0.1335 0.7008 0.036 Uiso 1 1 calc R U . . .
C11 C 0.9868(8) 0.2582(3) 0.4571(8) 0.0316(16) Uani 1 1 d . . . . .
H11 H 0.9713 0.2898 0.3956 0.038 Uiso 1 1 calc R U . . .
C13 C 1.1390(9) 0.1938(3) 0.6229(9) 0.0411(19) Uani 1 1 d . . . . .
H13 H 1.2284 0.1824 0.6735 0.049 Uiso 1 1 calc R U . . .
C8 C 0.6368(8) 0.2195(3) 0.4144(8) 0.0342(17) Uani 1 1 d . . . . .
C12 C 1.1125(10) 0.2414(3) 0.5288(10) 0.050(2) Uani 1 1 d . . . . .
H12 H 1.1849 0.2613 0.5171 0.060 Uiso 1 1 calc R U . . .
C18 C 0.8536(11) 0.0441(3) 1.2521(9) 0.056(3) Uani 1 1 d . . . . .
H18A H 0.9009 0.0614 1.3551 0.067 Uiso 1 1 calc R U . . .
H18B H 0.7636 0.0337 1.2521 0.067 Uiso 1 1 calc R U . . .
C4 C 0.5437(9) 0.1458(3) 0.5241(8) 0.042(2) Uani 1 1 d . . . . .
H4 H 0.5558 0.1144 0.5864 0.050 Uiso 1 1 calc R U . . .
C17 C 0.9058(8) 0.1338(3) 1.1781(9) 0.0407(19) Uani 1 1 d . . . . .
H17A H 0.8714 0.1482 1.2603 0.049 Uiso 1 1 calc R U . . .
H17B H 0.8826 0.1593 1.0887 0.049 Uiso 1 1 calc R U . . .
C7 C 0.5049(9) 0.2379(3) 0.3438(9) 0.048(2) Uani 1 1 d . . . . .
H7 H 0.4900 0.2693 0.2811 0.057 Uiso 1 1 calc R U . . .
C1 C 0.8133(8) 0.1035(3) 0.6795(8) 0.0372(19) Uani 1 1 d . . . . .
C6 C 0.3978(10) 0.2122(3) 0.3627(10) 0.054(2) Uani 1 1 d . . . . .
H6 H 0.3101 0.2258 0.3146 0.064 Uiso 1 1 calc R U . . .
O4 O 1.0321(10) 0.0076(3) 0.8797(7) 0.093(2) Uani 1 1 d . . . . .
C5 C 0.4185(9) 0.1644(3) 0.4555(9) 0.047(2) Uani 1 1 d . . . . .
H5 H 0.3445 0.1461 0.4685 0.057 Uiso 1 1 calc R U . . .
C19 C 0.9270(10) -0.0034(4) 1.2358(13) 0.076(4) Uani 1 1 d . . . . .
H19A H 1.0057 -0.0065 1.3334 0.091 Uiso 1 1 calc R U . . .
H19B H 0.8690 -0.0344 1.2335 0.091 Uiso 1 1 calc R U . . .
C16 C 1.0524(8) 0.1293(4) 1.2451(9) 0.048(2) Uani 1 1 d . . . . .
H14A H 1.0921 0.1650 1.2745 0.058 Uiso 1 1 calc R U . . .
H16B H 1.0770 0.1072 1.3424 0.058 Uiso 1 1 calc R U . . .
O1W O 0.5618(7) 0.0170(3) 0.3609(7) 0.0651(19) Uani 1 1 d . . . . .
C23 C 0.3725(10) 0.1219(6) 1.0067(13) 0.095(4) Uani 1 1 d D . . . .
H23A H 0.2841 0.1155 0.9284 0.142 Uiso 1 1 calc R U . A 1
H23B H 0.3763 0.1065 1.1088 0.142 Uiso 1 1 calc R U . A 1
H23C H 0.3886 0.1603 1.0190 0.142 Uiso 1 1 calc R U . A 1
O2W O 1.2960(7) 0.0411(3) 1.3082(12) 0.126(4) Uani 1 1 d . . . . .
C20 C 0.7029(13) 0.0768(5) 1.0093(14) 0.048(5) Uani 0.576(17) 1 d D . P B 1
H20A H 0.6777 0.0387 0.9983 0.058 Uiso 0.576(17) 1 calc R U P B 1
H20B H 0.6978 0.0905 0.9036 0.058 Uiso 0.576(17) 1 calc R U P B 1
C21 C 0.6106(13) 0.1069(5) 1.0710(16) 0.044(3) Uani 0.576(17) 1 d D . P B 1
H21A H 0.6334 0.1452 1.0789 0.053 Uiso 0.576(17) 1 calc R U P B 1
H21B H 0.6164 0.0938 1.1776 0.053 Uiso 0.576(17) 1 calc R U P B 1
C22 C 0.4714(13) 0.0982(6) 0.954(2) 0.044(3) Uani 0.576(17) 1 d D . P B 1
H22A H 0.4660 0.1134 0.8503 0.053 Uiso 0.576(17) 1 calc R U P B 1
H22B H 0.4538 0.0596 0.9402 0.053 Uiso 0.576(17) 1 calc R U P B 1
C20A C 0.6906(19) 0.1098(7) 1.0621(19) 0.028(4) Uiso 0.424(17) 1 d . . P B 2
H20C H 0.6647 0.1195 1.1553 0.033 Uiso 0.424(17) 1 calc R U P B 2
H20D H 0.6918 0.1427 1.0015 0.033 Uiso 0.424(17) 1 calc R U P B 2
C21A C 0.589(2) 0.0708(7) 0.957(2) 0.039(5) Uiso 0.424(17) 1 d . . P B 2
H21C H 0.5826 0.0396 1.0221 0.046 Uiso 0.424(17) 1 calc R U P B 2
H21D H 0.6215 0.0581 0.8718 0.046 Uiso 0.424(17) 1 calc R U P B 2
C22A C 0.444(2) 0.0955(9) 0.880(2) 0.042(6) Uiso 0.424(17) 1 d . . P B 2
H22C H 0.3839 0.0674 0.8171 0.050 Uiso 0.424(17) 1 calc R U P B 2
H22D H 0.4490 0.1237 0.8043 0.050 Uiso 0.424(17) 1 calc R U P B 2
H3O H 1.120(8) 0.0727(11) 1.152(9) 0.050 Uiso 1 1 d D U . . .
H1W H 0.6112 0.0449 0.3708 0.050 Uiso 1 1 d . U . . .
H2W H 0.5692 -0.0001 0.2808 0.050 Uiso 1 1 d . U . . .
H3W H 1.2874 0.0100 1.2638 0.050 Uiso 1 1 d . U . . .
H4W H 1.3483 0.0365 1.4035 0.050 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
Cu1 O4 1.917(7) . ?
Cu1 O4 1.921(6) 3_757 ?
Cu1 O1 1.940(5) . ?
Cu1 N1 2.031(7) . ?
Cu1 O3 2.303(9) . ?
Cu1 Cu1 2.922(2) 3_757 ?
O2 C1 1.252(8) . ?
C10 C9 1.387(11) . ?
C10 C11 1.416(10) . ?
C10 C15 1.440(8) . ?
C3 C2 1.404(11) . ?
C3 C4 1.433(10) . ?
C3 C8 1.444(9) . ?
C15 C2 1.402(10) . ?
C15 C14 1.422(10) . ?
N1 C17 1.466(9) . ?
N1 C20 1.473(13) . ?
N1 C18 1.491(8) . ?
N1 C20A 1.637(19) . ?
C9 C8 1.394(11) . ?
C9 H9 0.9500 . ?
C2 C1 1.509(9) . ?
O3 C16 1.419(10) . ?
O3 H3O 0.86(2) . ?
O1 C1 1.264(8) . ?
C14 C13 1.364(10) . ?
C14 H14 0.9500 . ?
C11 C12 1.341(12) . ?
C11 H11 0.9500 . ?
C13 C12 1.436(10) . ?
C13 H13 0.9500 . ?
C8 C7 1.409(11) . ?
C12 H12 0.9500 . ?
C18 C19 1.459(13) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C4 C5 1.348(11) . ?
C4 H4 0.9500 . ?
C17 C16 1.473(11) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C7 C6 1.365(12) . ?
C7 H7 0.9500 . ?
C6 C5 1.434(12) . ?
C6 H6 0.9500 . ?
O4 C19 1.249(10) 3_757 ?
O4 Cu1 1.921(6) 3_757 ?
C5 H5 0.9500 . ?
C19 O4 1.249(10) 3_757 ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C16 H14A 0.9900 . ?
C16 H16B 0.9900 . ?
O1W H1W 0.862(6) . ?
O1W H2W 0.859(6) . ?
C23 C22 1.413(14) . ?
C23 C22A 1.69(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O2W H3W 0.868(10) . ?
O2W H4W 0.856(8) . ?
C20 C21 1.481(15) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.514(15) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C20A C21A 1.53(3) . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C21A C22A 1.59(3) . ?
C21A H21C 0.9900 . ?
C21A H21D 0.9900 . ?
C22A H22C 0.9900 . ?
C22A H22D 0.9900 . ?

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
O4 Cu1 O4 80.8(3) . 3_757 ?
O4 Cu1 O1 100.2(3) . . ?
O4 Cu1 O1 173.8(3) 3_757 . ?
O4 Cu1 N1 165.1(2) . . ?
O4 Cu1 N1 84.3(3) 3_757 . ?
O1 Cu1 N1 94.5(2) . . ?
O4 Cu1 O3 101.0(3) . . ?
O4 Cu1 O3 97.3(3) 3_757 . ?
O1 Cu1 O3 88.5(2) . . ?
N1 Cu1 O3 81.2(3) . . ?
O4 Cu1 Cu1 40.48(17) . 3_757 ?
O4 Cu1 Cu1 40.4(2) 3_757 3_757 ?
O1 Cu1 Cu1 140.34(19) . 3_757 ?
N1 Cu1 Cu1 124.66(17) . 3_757 ?
O3 Cu1 Cu1 102.04(19) . 3_757 ?
C9 C10 C11 121.3(6) . . ?
C9 C10 C15 119.2(7) . . ?
C11 C10 C15 119.5(7) . . ?
C2 C3 C4 124.1(6) . . ?
C2 C3 C8 119.0(7) . . ?
C4 C3 C8 116.9(7) . . ?
C2 C15 C14 123.2(6) . . ?
C2 C15 C10 119.0(7) . . ?
C14 C15 C10 117.8(6) . . ?
C17 N1 C20 125.3(7) . . ?
C17 N1 C18 112.9(6) . . ?
C20 N1 C18 106.5(8) . . ?
C17 N1 C20A 92.9(8) . . ?
C18 N1 C20A 111.0(8) . . ?
C17 N1 Cu1 105.7(5) . . ?
C20 N1 Cu1 96.6(6) . . ?
C18 N1 Cu1 107.6(5) . . ?
C20A N1 Cu1 125.7(7) . . ?
C10 C9 C8 122.3(6) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C15 C2 C3 121.5(6) . . ?
C15 C2 C1 119.9(7) . . ?
C3 C2 C1 118.5(6) . . ?
C16 O3 Cu1 105.3(6) . . ?
C16 O3 H3O 111(5) . . ?
Cu1 O3 H3O 67(6) . . ?
C1 O1 Cu1 125.0(4) . . ?
C13 C14 C15 121.3(6) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C12 C11 C10 120.9(6) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C14 C13 C12 119.7(8) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C9 C8 C7 122.1(7) . . ?
C9 C8 C3 119.0(7) . . ?
C7 C8 C3 119.0(7) . . ?
C11 C12 C13 120.8(8) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C19 C18 N1 112.1(7) . . ?
C19 C18 H18A 109.2 . . ?
N1 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
N1 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C5 C4 C3 122.9(7) . . ?
C5 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
N1 C17 C16 113.1(6) . . ?
N1 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
N1 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C6 C7 C8 122.1(8) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
O2 C1 O1 125.6(6) . . ?
O2 C1 C2 119.0(6) . . ?
O1 C1 C2 115.4(6) . . ?
C7 C6 C5 119.6(8) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C19 O4 Cu1 144.4(6) 3_757 . ?
C19 O4 Cu1 116.4(6) 3_757 3_757 ?
Cu1 O4 Cu1 99.2(3) . 3_757 ?
C4 C5 C6 119.5(8) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
O4 C19 C18 119.6(7) 3_757 . ?
O4 C19 H19A 107.4 3_757 . ?
C18 C19 H19A 107.4 . . ?
O4 C19 H19B 107.4 3_757 . ?
C18 C19 H19B 107.4 . . ?
H19A C19 H19B 106.9 . . ?
O3 C16 C17 110.2(7) . . ?
O3 C16 H14A 109.6 . . ?
C17 C16 H14A 109.6 . . ?
O3 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H14A C16 H16B 108.1 . . ?
H1W O1W H2W 105.8(6) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H3W O2W H4W 105.5(6) . . ?
N1 C20 C21 108.5(10) . . ?
N1 C20 H20A 110.0 . . ?
C21 C20 H20A 110.0 . . ?
N1 C20 H20B 110.0 . . ?
C21 C20 H20B 110.0 . . ?
H20A C20 H20B 108.4 . . ?
C20 C21 C22 106.5(11) . . ?
C20 C21 H21A 110.4 . . ?
C22 C21 H21A 110.4 . . ?
C20 C21 H21B 110.4 . . ?
C22 C21 H21B 110.4 . . ?
H21A C21 H21B 108.6 . . ?
C23 C22 C21 111.9(12) . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C21A C20A N1 110.0(13) . . ?
C21A C20A H20C 109.7 . . ?
N1 C20A H20C 109.7 . . ?
C21A C20A H20D 109.7 . . ?
N1 C20A H20D 109.7 . . ?
H20C C20A H20D 108.2 . . ?
C20A C21A C22A 113.6(15) . . ?
C20A C21A H21C 108.9 . . ?
C22A C21A H21C 108.9 . . ?
C20A C21A H21D 108.9 . . ?
C22A C21A H21D 108.8 . . ?
H21C C21A H21D 107.7 . . ?
C21A C22A C23 116.2(15) . . ?
C21A C22A H22C 108.2 . . ?
C23 C22A H22C 108.2 . . ?
C21A C22A H22D 108.2 . . ?
C23 C22A H22D 108.2 . . ?
H22C C22A H22D 107.4 . . ?

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
C9 C10 C15 C2 0.9(9) . . . . ?
C11 C10 C15 C2 -179.9(6) . . . . ?
C9 C10 C15 C14 179.6(6) . . . . ?
C11 C10 C15 C14 -1.3(9) . . . . ?
C11 C10 C9 C8 -178.4(6) . . . . ?
C15 C10 C9 C8 0.8(9) . . . . ?
C14 C15 C2 C3 179.7(6) . . . . ?
C10 C15 C2 C3 -1.7(9) . . . . ?
C14 C15 C2 C1 1.6(9) . . . . ?
C10 C15 C2 C1 -179.9(6) . . . . ?
C4 C3 C2 C15 -176.3(6) . . . . ?
C8 C3 C2 C15 0.8(9) . . . . ?
C4 C3 C2 C1 1.9(10) . . . . ?
C8 C3 C2 C1 179.0(6) . . . . ?
C2 C15 C14 C13 179.9(6) . . . . ?
C10 C15 C14 C13 1.3(9) . . . . ?
C9 C10 C11 C12 179.9(7) . . . . ?
C15 C10 C11 C12 0.8(10) . . . . ?
C15 C14 C13 C12 -0.8(10) . . . . ?
C10 C9 C8 C7 177.9(6) . . . . ?
C10 C9 C8 C3 -1.7(10) . . . . ?
C2 C3 C8 C9 0.9(9) . . . . ?
C4 C3 C8 C9 178.2(6) . . . . ?
C2 C3 C8 C7 -178.7(6) . . . . ?
C4 C3 C8 C7 -1.4(9) . . . . ?
C10 C11 C12 C13 -0.2(11) . . . . ?
C14 C13 C12 C11 0.2(11) . . . . ?
C17 N1 C18 C19 -117.4(9) . . . . ?
C20 N1 C18 C19 101.5(10) . . . . ?
C20A N1 C18 C19 139.8(10) . . . . ?
Cu1 N1 C18 C19 -1.2(10) . . . . ?
C2 C3 C4 C5 178.4(7) . . . . ?
C8 C3 C4 C5 1.3(10) . . . . ?
C20 N1 C17 C16 -161.1(8) . . . . ?
C18 N1 C17 C16 66.4(9) . . . . ?
C20A N1 C17 C16 -179.3(8) . . . . ?
Cu1 N1 C17 C16 -50.9(7) . . . . ?
C9 C8 C7 C6 -178.4(7) . . . . ?
C3 C8 C7 C6 1.2(11) . . . . ?
Cu1 O1 C1 O2 3.6(13) . . . . ?
Cu1 O1 C1 C2 -177.2(5) . . . . ?
C15 C2 C1 O2 -121.8(8) . . . . ?
C3 C2 C1 O2 59.9(10) . . . . ?
C15 C2 C1 O1 59.0(10) . . . . ?
C3 C2 C1 O1 -119.3(8) . . . . ?
C8 C7 C6 C5 -0.7(12) . . . . ?
C3 C4 C5 C6 -0.9(11) . . . . ?
C7 C6 C5 C4 0.6(12) . . . . ?
N1 C18 C19 O4 -0.8(15) . . . 3_757 ?
Cu1 O3 C16 C17 -28.5(8) . . . . ?
N1 C17 C16 O3 55.4(9) . . . . ?
C17 N1 C20 C21 -53.7(13) . . . . ?
C18 N1 C20 C21 81.2(11) . . . . ?
Cu1 N1 C20 C21 -168.2(9) . . . . ?
N1 C20 C21 C22 -178.5(10) . . . . ?
C20 C21 C22 C23 175.6(12) . . . . ?
C17 N1 C20A C21A 167.1(12) . . . . ?
C18 N1 C20A C21A -77.0(13) . . . . ?
Cu1 N1 C20A C21A 55.4(15) . . . . ?
N1 C20A C21A C22A -174.1(13) . . . . ?
C20A C21A C22A C23 -56(2) . . . . ?

_refine_diff_density_max         1.545
_refine_diff_density_min         -1.703
_refine_diff_density_rms         0.121

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

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

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1936226'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;CQE, Instituto Superior Tecnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2019-06-24 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H44 Cu2 N2 O8'
_chemical_formula_weight         687.75

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'
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                   16.608(2)
_cell_length_b                   11.434(4)
_cell_length_c                   16.771(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.803(6)
_cell_angle_gamma                90
_cell_volume                     3128.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5751
_cell_measurement_theta_min      2.175
_cell_measurement_theta_max      25.649

_exptl_crystal_description       block
_exptl_crystal_colour            blue


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.411
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.920

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  0.919

_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)


_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25910
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_av_R_equivalents  0.1301
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.175
_diffrn_reflns_theta_max         25.649
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             5751
_reflns_number_gt                3113
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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


_computing_data_collection       'BRUKER SMART (Bruker, 2005)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.2'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0917P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5751
_refine_ls_number_parameters     380
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1642
_refine_ls_wR_factor_gt          0.1368
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_restrained_S_all      0.911
_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 0.1780(3) -0.0463(5) 0.0116(3) 0.0437(13) Uani 1 1 d . . . . .
C2 C 0.1931(3) -0.0245(5) -0.0714(3) 0.0394(12) Uani 1 1 d . . . . .
C3 C 0.2102(4) 0.0869(5) -0.0947(3) 0.0530(15) Uani 1 1 d . . . . .
H3 H 0.2100 0.1489 -0.0589 0.064 Uiso 1 1 calc R U . . .
C7 C 0.1923(3) -0.1145(5) -0.1256(3) 0.0426(13) Uani 1 1 d . . . . .
H7 H 0.1806 -0.1900 -0.1107 0.051 Uiso 1 1 calc R U . . .
C13 C 0.0725(4) 0.2660(6) 0.1327(5) 0.076(2) Uani 1 1 d . . . . .
H13A H 0.0794 0.2985 0.1870 0.091 Uiso 1 1 calc R U . . .
H13B H 0.1267 0.2523 0.1209 0.091 Uiso 1 1 calc R U . . .
C14 C 0.0303(6) 0.3524(8) 0.0749(6) 0.123(4) Uani 1 1 d D . . . .
H14A H -0.0253 0.3615 0.0841 0.148 Uiso 1 1 calc R U . . .
H14B H 0.0577 0.4272 0.0861 0.148 Uiso 1 1 calc R U . . .
C15 C 0.0272(11) 0.3246(11) -0.0076(7) 0.197(7) Uani 1 1 d D . . . .
H15A H 0.0816 0.3256 -0.0193 0.296 Uiso 1 1 calc R U . . .
H15B H -0.0061 0.3811 -0.0411 0.296 Uiso 1 1 calc R U . . .
H15C H 0.0039 0.2481 -0.0186 0.296 Uiso 1 1 calc R U . . .
C19 C 0.5052(4) 0.1106(6) 0.3559(4) 0.0627(18) Uani 1 1 d . . . . .
H19A H 0.5025 0.0739 0.4074 0.075 Uiso 1 1 calc R U . . .
H19B H 0.5558 0.1550 0.3621 0.075 Uiso 1 1 calc R U . . .
O1 O 0.1735(3) -0.1485(4) 0.0349(3) 0.0703(13) Uani 1 1 d . . . . .
O6 O 0.4367(2) 0.1868(4) 0.3326(2) 0.0578(11) Uani 1 1 d . . . . .
H6O H 0.4206 0.2094 0.3733 0.087 Uiso 1 1 calc R U . . .
C22 C 0.4205(6) -0.3406(9) 0.4062(6) 0.129(3) Uani 1 1 d D U . . .
H22A H 0.3842 -0.4071 0.3931 0.154 Uiso 1 1 calc R U . . .
H22B H 0.4744 -0.3629 0.3970 0.154 Uiso 1 1 calc R U . . .
C23 C 0.4249(10) -0.3121(15) 0.4816(7) 0.263(11) Uani 1 1 d D U . . .
H23A H 0.3981 -0.2383 0.4848 0.394 Uiso 1 1 calc R U . . .
H23B H 0.4813 -0.3059 0.5076 0.394 Uiso 1 1 calc R U . . .
H23C H 0.3984 -0.3710 0.5084 0.394 Uiso 1 1 calc R U . . .
H3O H 0.159(5) -0.167(8) 0.1349(15) 0.11(3) Uiso 1 1 d D . . . .
C4 C 0.2279(4) 0.1074(5) -0.1712(3) 0.0601(17) Uani 1 1 d . . . . .
H4 H 0.2394 0.1832 -0.1858 0.072 Uiso 1 1 calc R U . . .
C5 C 0.2288(3) 0.0164(5) -0.2267(3) 0.0399(13) Uani 1 1 d . . . . .
C6 C 0.2087(3) -0.0939(5) -0.2028(3) 0.0456(13) Uani 1 1 d . . . . .
H6 H 0.2060 -0.1558 -0.2392 0.055 Uiso 1 1 calc R U . . .
C8 C 0.0833(4) -0.1576(6) 0.1998(5) 0.074(2) Uani 1 1 d . . . . .
H8A H 0.0823 -0.1595 0.2574 0.089 Uiso 1 1 calc R U . . .
H8B H 0.0578 -0.2289 0.1759 0.089 Uiso 1 1 calc R U . . .
C9 C 0.0343(4) -0.0550(6) 0.1624(4) 0.0631(18) Uani 1 1 d . . . . .
H9A H 0.0258 -0.0622 0.1038 0.076 Uiso 1 1 calc R U . . .
H9B H -0.0191 -0.0570 0.1780 0.076 Uiso 1 1 calc R U . . .
C10 C 0.1580(3) 0.0596(7) 0.3267(3) 0.0588(18) Uani 1 1 d . . . . .
H10A H 0.1643 0.1002 0.3783 0.071 Uiso 1 1 calc R U . . .
H10B H 0.1611 -0.0239 0.3370 0.071 Uiso 1 1 calc R U . . .
C11 C 0.0773(3) 0.0907(8) 0.2737(4) 0.071(2) Uani 1 1 d . . . . .
H11A H 0.0337 0.0499 0.2934 0.085 Uiso 1 1 calc R U . . .
H11B H 0.0679 0.1740 0.2782 0.085 Uiso 1 1 calc R U . . .
C12 C 0.0286(3) 0.1505(6) 0.1314(4) 0.0590(17) Uani 1 1 d . . . . .
H12A H -0.0244 0.1636 0.1464 0.071 Uiso 1 1 calc R U . . .
H12B H 0.0188 0.1203 0.0764 0.071 Uiso 1 1 calc R U . . .
C16 C 0.3646(4) -0.0105(7) 0.1489(4) 0.069(2) Uani 1 1 d . . . . .
H16A H 0.4040 0.0445 0.1346 0.083 Uiso 1 1 calc R U . . .
H16B H 0.3348 -0.0452 0.0993 0.083 Uiso 1 1 calc R U . . .
C17 C 0.4086(4) -0.1044(7) 0.2031(4) 0.071(2) Uani 1 1 d . . . . .
H17A H 0.3730 -0.1719 0.2023 0.085 Uiso 1 1 calc R U . . .
H17B H 0.4570 -0.1286 0.1830 0.085 Uiso 1 1 calc R U . . .
C18 C 0.5039(3) 0.0212(6) 0.2935(4) 0.0588(17) Uani 1 1 d . . . . .
H18A H 0.5545 -0.0233 0.3052 0.071 Uiso 1 1 calc R U . . .
H18B H 0.5015 0.0591 0.2413 0.071 Uiso 1 1 calc R U . . .
C20 C 0.4570(4) -0.1589(6) 0.3462(4) 0.0691(19) Uani 1 1 d . U . . .
H20A H 0.5011 -0.2025 0.3293 0.083 Uiso 1 1 calc R U . . .
H20B H 0.4782 -0.1265 0.3994 0.083 Uiso 1 1 calc R U . . .
C21 C 0.3893(6) -0.2408(9) 0.3528(7) 0.129(3) Uani 1 1 d D U . . .
H21A H 0.3472 -0.2000 0.3748 0.154 Uiso 1 1 calc R U . . .
H21B H 0.3649 -0.2696 0.2993 0.154 Uiso 1 1 calc R U . . .
C24 C 0.3349(3) 0.0957(6) 0.4679(3) 0.0486(14) Uani 1 1 d . . . . .
C25 C 0.3045(3) 0.0728(5) 0.5446(3) 0.0417(13) Uani 1 1 d . . . . .
C26 C 0.2723(4) -0.0335(5) 0.5620(3) 0.0533(15) Uani 1 1 d . . . . .
H26 H 0.2679 -0.0942 0.5245 0.064 Uiso 1 1 calc R U . . .
C27 C 0.2467(4) -0.0499(5) 0.6343(3) 0.0538(15) Uani 1 1 d . . . . .
H27 H 0.2239 -0.1216 0.6440 0.065 Uiso 1 1 calc R U . . .
C28 C 0.2533(3) 0.0366(5) 0.6939(3) 0.0390(12) Uani 1 1 d . . . . .
C29 C 0.2867(3) 0.1434(5) 0.6749(3) 0.0447(13) Uani 1 1 d . . . . .
H29 H 0.2927 0.2037 0.7128 0.054 Uiso 1 1 calc R U . . .
C30 C 0.3106(3) 0.1611(5) 0.6028(3) 0.0459(13) Uani 1 1 d . . . . .
H30 H 0.3314 0.2337 0.5920 0.055 Uiso 1 1 calc R U . . .
N1 N 0.0734(2) 0.0606(4) 0.1864(3) 0.0475(12) Uani 1 1 d . . . . .
N2 N 0.4328(3) -0.0609(4) 0.2880(3) 0.0513(12) Uani 1 1 d . . . . .
O2 O 0.1725(2) 0.0436(3) 0.0556(2) 0.0470(9) Uani 1 1 d . . . . .
O3 O 0.1661(3) -0.1547(4) 0.1890(3) 0.0632(11) Uani 1 1 d D . . . .
O4 O 0.2198(2) 0.0944(4) 0.2842(2) 0.0455(9) Uani 1 1 d . . . . .
O5 O 0.3101(2) 0.0480(4) 0.1893(2) 0.0489(10) Uani 1 1 d . . . . .
O7 O 0.3347(2) 0.0088(4) 0.4188(2) 0.0490(10) Uani 1 1 d . . . . .
O8 O 0.3602(3) 0.1960(4) 0.4553(3) 0.0724(13) Uani 1 1 d . . . . .
Cu1 Cu 0.19298(3) 0.04994(6) 0.17222(3) 0.0375(2) Uani 1 1 d . . . . .
Cu2 Cu 0.33157(4) 0.03401(6) 0.30480(4) 0.0403(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.239(7) . ?
C1 O2 1.278(7) . ?
C1 C2 1.481(7) . ?
C2 C7 1.371(7) . ?
C2 C3 1.378(8) . ?
C3 C4 1.389(8) . ?
C7 C6 1.391(7) . ?
C13 C14 1.467(10) . ?
C13 C12 1.508(9) . ?
C14 C15 1.412(11) . ?
C19 O6 1.428(7) . ?
C19 C18 1.460(9) . ?
C22 C23 1.296(11) . ?
C22 C21 1.482(11) . ?
C4 C5 1.397(8) . ?
C5 C6 1.383(8) . ?
C5 C28 1.482(7) 1_554 ?
C8 O3 1.420(8) . ?
C8 C9 1.496(9) . ?
C9 N1 1.495(8) . ?
C10 O4 1.413(7) . ?
C10 C11 1.506(8) . ?
C11 N1 1.494(8) . ?
C12 N1 1.484(7) . ?
C16 O5 1.398(7) . ?
C16 C17 1.505(10) . ?
C17 N2 1.491(8) . ?
C18 N2 1.498(7) . ?
C20 C21 1.484(11) . ?
C20 N2 1.491(8) . ?
C24 O8 1.252(8) . ?
C24 O7 1.289(7) . ?
C24 C25 1.491(8) . ?
C25 C26 1.381(8) . ?
C25 C30 1.396(8) . ?
C26 C27 1.372(8) . ?
C27 C28 1.396(7) . ?
C28 C29 1.403(8) . ?
C28 C5 1.482(7) 1_556 ?
C29 C30 1.356(7) . ?
N1 Cu1 2.048(4) . ?
N2 Cu2 2.064(5) . ?
O2 Cu1 1.922(3) . ?
O3 Cu1 2.408(5) . ?
O4 Cu1 1.916(3) . ?
O4 Cu2 1.949(3) . ?
O5 Cu2 1.910(3) . ?
O5 Cu1 1.912(4) . ?
O7 Cu2 1.925(4) . ?
Cu1 Cu2 2.8908(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
O1 C1 O2 124.1(5) . . ?
O1 C1 C2 119.1(5) . . ?
O2 C1 C2 116.8(5) . . ?
C7 C2 C3 118.8(5) . . ?
C7 C2 C1 121.0(5) . . ?
C3 C2 C1 120.1(5) . . ?
C2 C3 C4 120.6(5) . . ?
C2 C7 C6 120.7(5) . . ?
C14 C13 C12 114.3(6) . . ?
C15 C14 C13 114.9(9) . . ?
O6 C19 C18 109.1(5) . . ?
C23 C22 C21 110.2(12) . . ?
C3 C4 C5 121.3(6) . . ?
C6 C5 C4 116.9(5) . . ?
C6 C5 C28 121.6(5) . 1_554 ?
C4 C5 C28 121.4(5) . 1_554 ?
C5 C6 C7 121.6(5) . . ?
O3 C8 C9 113.1(6) . . ?
N1 C9 C8 114.0(5) . . ?
O4 C10 C11 106.6(5) . . ?
N1 C11 C10 113.3(5) . . ?
N1 C12 C13 114.4(5) . . ?
O5 C16 C17 109.5(5) . . ?
N2 C17 C16 110.6(6) . . ?
C19 C18 N2 112.8(5) . . ?
C21 C20 N2 114.1(5) . . ?
C22 C21 C20 110.3(8) . . ?
O8 C24 O7 124.0(6) . . ?
O8 C24 C25 119.0(5) . . ?
O7 C24 C25 117.0(6) . . ?
C26 C25 C30 118.0(5) . . ?
C26 C25 C24 123.0(5) . . ?
C30 C25 C24 119.0(5) . . ?
C27 C26 C25 120.2(5) . . ?
C26 C27 C28 122.8(6) . . ?
C27 C28 C29 115.8(5) . . ?
C27 C28 C5 122.4(5) . 1_556 ?
C29 C28 C5 121.8(5) . 1_556 ?
C30 C29 C28 121.8(5) . . ?
C29 C30 C25 121.4(6) . . ?
C12 N1 C11 112.0(5) . . ?
C12 N1 C9 107.6(4) . . ?
C11 N1 C9 113.8(5) . . ?
C12 N1 Cu1 110.7(4) . . ?
C11 N1 Cu1 105.2(3) . . ?
C9 N1 Cu1 107.3(4) . . ?
C17 N2 C20 111.4(5) . . ?
C17 N2 C18 109.6(5) . . ?
C20 N2 C18 108.5(4) . . ?
C17 N2 Cu2 103.0(3) . . ?
C20 N2 Cu2 115.7(4) . . ?
C18 N2 Cu2 108.4(4) . . ?
C1 O2 Cu1 126.8(3) . . ?
C8 O3 Cu1 104.0(4) . . ?
C10 O4 Cu1 111.3(3) . . ?
C10 O4 Cu2 124.6(3) . . ?
Cu1 O4 Cu2 96.82(16) . . ?
C16 O5 Cu2 115.9(3) . . ?
C16 O5 Cu1 131.8(4) . . ?
Cu2 O5 Cu1 98.30(17) . . ?
C24 O7 Cu2 121.0(4) . . ?
O5 Cu1 O4 79.23(14) . . ?
O5 Cu1 O2 97.62(16) . . ?
O4 Cu1 O2 166.28(18) . . ?
O5 Cu1 N1 164.75(17) . . ?
O4 Cu1 N1 85.58(17) . . ?
O2 Cu1 N1 97.47(17) . . ?
O5 Cu1 O3 100.19(17) . . ?
O4 Cu1 O3 99.07(16) . . ?
O2 Cu1 O3 94.63(16) . . ?
N1 Cu1 O3 80.75(18) . . ?
O5 Cu1 Cu2 40.83(10) . . ?
O4 Cu1 Cu2 42.03(10) . . ?
O2 Cu1 Cu2 138.03(12) . . ?
N1 Cu1 Cu2 124.35(13) . . ?
O3 Cu1 Cu2 89.29(11) . . ?
O5 Cu2 O7 170.21(16) . . ?
O5 Cu2 O4 78.44(14) . . ?
O7 Cu2 O4 94.40(16) . . ?
O5 Cu2 N2 84.72(17) . . ?
O7 Cu2 N2 100.70(18) . . ?
O4 Cu2 N2 159.19(17) . . ?
O5 Cu2 Cu1 40.87(11) . . ?
O7 Cu2 Cu1 130.01(12) . . ?
O4 Cu2 Cu1 41.14(10) . . ?
N2 Cu2 Cu1 118.67(13) . . ?

_refine_diff_density_max         0.910
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.108

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

