# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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 1567317'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H34 Cu2 N10 O2'
_chemical_formula_weight         645.71

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                   19.302(6)
_cell_length_b                   7.5206(19)
_cell_length_c                   20.583(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.211(13)
_cell_angle_gamma                90
_cell_volume                     2785.4(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1840
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.571
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15691
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.123
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_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             2450
_reflns_number_gt                2108
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0417P)²+3.6560P] 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         2450
_refine_ls_number_parameters     181
_refine_ls_number_restraints     309
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.007
_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 0.25466(2) 0.06474(4) -0.03722(2) 0.03650(14) Uani 1 1 d . U . . .
C7 C 0.29939(17) -0.0465(4) -0.15079(16) 0.0482(7) Uani 1 1 d . U . . .
H7 H 0.334561 -0.095703 -0.166666 0.058 Uiso 1 1 calc R U . . .
N5 N 0.06031(14) 0.1393(5) -0.03331(16) 0.0688(8) Uani 1 1 d . U . . .
C3 C 0.0950(2) 0.0763(5) -0.30792(17) 0.0619(9) Uani 1 1 d . U . . .
H3 H 0.050029 0.101653 -0.343409 0.074 Uiso 1 1 calc R U . . .
O1 O 0.17730(10) 0.1281(3) -0.12178(10) 0.0478(5) Uani 1 1 d . U . . .
N4 N 0.12369(13) 0.1275(3) -0.01045(12) 0.0414(5) Uani 1 1 d . U . . .
N1 N 0.31804(13) -0.0258(3) -0.08500(13) 0.0443(6) Uani 1 1 d . U . . .
N3 N 0.19003(12) 0.1202(3) 0.01609(12) 0.0419(6) Uani 1 1 d . U . . .
C6 C 0.22913(17) -0.0005(4) -0.20178(15) 0.0454(7) Uani 1 1 d . U . . .
N2 N 0.33910(12) -0.0156(3) 0.05005(12) 0.0410(5) Uani 1 1 d . U . . .
H2 H 0.370040 0.089885 0.067696 0.049 Uiso 1 1 calc R U . . .
C4 C 0.1504(2) -0.0061(6) -0.32359(18) 0.0711(10) Uani 1 1 d . U . . .
H4 H 0.143050 -0.036819 -0.369389 0.085 Uiso 1 1 calc R U . . .
C8 C 0.39231(16) -0.0758(5) -0.03790(17) 0.0543(8) Uani 1 1 d . U . . .
H8A H 0.425107 0.026505 -0.028241 0.065 Uiso 1 1 calc R U . . .
H8B H 0.412577 -0.167383 -0.059069 0.065 Uiso 1 1 calc R U . . .
C5 C 0.2164(2) -0.0427(5) -0.27156(17) 0.0609(9) Uani 1 1 d . U . . .
H5 H 0.253967 -0.097221 -0.282591 0.073 Uiso 1 1 calc R U . . .
C13 C 0.32399(17) -0.0895(4) 0.10999(16) 0.0509(8) Uani 1 1 d . U . . .
H13A H 0.295525 -0.198383 0.095814 0.061 Uiso 1 1 calc R U . . .
H13B H 0.294177 -0.005595 0.124387 0.061 Uiso 1 1 calc R U . . .
C1 C 0.17173(15) 0.0843(4) -0.18475(15) 0.0417(6) Uani 1 1 d . U . . .
C12 C 0.39484(18) -0.1287(5) 0.17126(17) 0.0567(8) Uani 1 1 d . U . . .
H12A H 0.382424 -0.186969 0.207664 0.068 Uiso 1 1 calc R U . . .
H12B H 0.419656 -0.017680 0.189911 0.068 Uiso 1 1 calc R U . . .
C2 C 0.10515(17) 0.1220(5) -0.24046(16) 0.0528(8) Uani 1 1 d . U . . .
H2A H 0.066951 0.179350 -0.231355 0.063 Uiso 1 1 calc R U . . .
C9 C 0.38632(16) -0.1431(4) 0.02775(17) 0.0503(7) Uani 1 1 d . U . . .
H9 H 0.359785 -0.256748 0.017066 0.060 Uiso 1 1 calc R U . . .
C11 C 0.44730(17) -0.2465(5) 0.15054(17) 0.0558(8) Uani 1 1 d . U . . .
H11A H 0.494454 -0.254623 0.189186 0.067 Uiso 1 1 calc R U . . .
H11B H 0.426549 -0.365317 0.140669 0.067 Uiso 1 1 calc R U . . .
C10 C 0.46026(16) -0.1759(5) 0.08756(17) 0.0565(8) Uani 1 1 d . U . . .
H10A H 0.489527 -0.260670 0.072863 0.068 Uiso 1 1 calc R U . . .
H10B H 0.488015 -0.065518 0.099443 0.068 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 1.899(2) . ?
Cu1 N1 1.949(2) . ?
Cu1 N3 1.981(2) . ?
Cu1 N2 2.032(2) . ?
C7 N1 1.279(4) . ?
C7 C6 1.425(4) . ?
C7 H7 0.9300 . ?
N5 N4 1.144(3) . ?
C3 C2 1.374(5) . ?
C3 C4 1.372(5) . ?
C3 H3 0.9300 . ?
O1 C1 1.304(3) . ?
N4 N3 1.198(3) . ?
N1 C8 1.460(4) . ?
C6 C5 1.403(4) . ?
C6 C1 1.427(4) . ?
N2 C13 1.476(4) . ?
N2 C9 1.505(4) . ?
N2 H2 0.9800 . ?
C4 C5 1.363(5) . ?
C4 H4 0.9300 . ?
C8 C9 1.486(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 H5 0.9300 . ?
C13 C12 1.516(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C1 C2 1.407(4) . ?
C12 C11 1.518(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C2 H2A 0.9300 . ?
C9 C10 1.530(4) . ?
C9 H9 0.9800 . ?
C11 C10 1.503(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 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 N1 93.11(9) . . ?
O1 Cu1 N3 90.62(9) . . ?
N1 Cu1 N3 171.54(10) . . ?
O1 Cu1 N2 176.46(9) . . ?
N1 Cu1 N2 83.86(10) . . ?
N3 Cu1 N2 92.15(9) . . ?
N1 C7 C6 125.4(3) . . ?
N1 C7 H7 117.3 . . ?
C6 C7 H7 117.3 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C1 O1 Cu1 127.04(18) . . ?
N5 N4 N3 176.8(3) . . ?
C7 N1 C8 120.3(2) . . ?
C7 N1 Cu1 126.1(2) . . ?
C8 N1 Cu1 113.57(19) . . ?
N4 N3 Cu1 122.72(19) . . ?
C5 C6 C7 117.8(3) . . ?
C5 C6 C1 119.2(3) . . ?
C7 C6 C1 123.0(3) . . ?
C13 N2 C9 109.9(2) . . ?
C13 N2 Cu1 120.87(18) . . ?
C9 N2 Cu1 107.49(18) . . ?
C13 N2 H2 105.9 . . ?
C9 N2 H2 105.9 . . ?
Cu1 N2 H2 105.9 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C8 C9 108.1(2) . . ?
N1 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
N1 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C4 C5 C6 121.8(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
N2 C13 C12 112.1(2) . . ?
N2 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
N2 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O1 C1 C2 118.8(3) . . ?
O1 C1 C6 124.4(3) . . ?
C2 C1 C6 116.8(3) . . ?
C13 C12 C11 111.9(3) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 H2A 119.1 . . ?
C1 C2 H2A 119.1 . . ?
C8 C9 N2 108.4(2) . . ?
C8 C9 C10 115.5(2) . . ?
N2 C9 C10 110.4(3) . . ?
C8 C9 H9 107.4 . . ?
N2 C9 H9 107.4 . . ?
C10 C9 H9 107.4 . . ?
C10 C11 C12 111.8(3) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C10 C9 110.7(2) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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 1567318'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H44 Cu2 N4 O8'
_chemical_formula_weight         715.77

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                   8.654(2)
_cell_length_b                   8.757(2)
_cell_length_c                   11.861(3)
_cell_angle_alpha                101.973(5)
_cell_angle_beta                 101.335(3)
_cell_angle_gamma                109.734(5)
_cell_volume                     792.2(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1750
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             374
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    1.397
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6830
_diffrn_reflns_av_unetI/netI     0.0803
_diffrn_reflns_av_R_equivalents  0.0619
_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       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.834
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2780
_reflns_number_gt                2017
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0700P)²] 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         2780
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1417
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.060
_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 1.00239(8) 0.19301(7) 0.98659(5) 0.0251(2) Uani 1 1 d . . . . .
O2 O 0.8669(4) 0.0145(4) 1.0442(3) 0.0244(7) Uani 1 1 d . . . . .
O3 O 0.7275(4) 0.1785(4) 1.0898(3) 0.0331(8) Uani 1 1 d . . . . .
O1 O 0.8344(4) 0.0963(4) 0.8305(3) 0.0282(8) Uani 1 1 d . . . . .
N1 N 1.1428(5) 0.3776(5) 0.9376(3) 0.0252(9) Uani 1 1 d . . . . .
C8 C 1.2841(6) 0.5127(6) 1.0367(4) 0.0313(12) Uani 1 1 d . . . . .
H8A H 1.297392 0.622692 1.025730 0.038 Uiso 1 1 calc R U . . .
H8B H 1.390452 0.498004 1.037591 0.038 Uiso 1 1 calc R U . . .
N2 N 1.1772(5) 0.3230(5) 1.1499(3) 0.0286(9) Uani 1 1 d . . . . .
H2 H 1.272862 0.287244 1.149450 0.034 Uiso 1 1 calc R U . . .
C13 C 1.1344(6) 0.3057(6) 1.2618(4) 0.0314(12) Uani 1 1 d . . . . .
H13A H 1.098185 0.187428 1.260143 0.038 Uiso 1 1 calc R U . . .
H13B H 1.039026 0.338849 1.266276 0.038 Uiso 1 1 calc R U . . .
C10 C 1.3974(7) 0.6163(7) 1.2616(4) 0.0378(13) Uani 1 1 d . . . . .
H10A H 1.430348 0.734045 1.262307 0.045 Uiso 1 1 calc R U . . .
H10B H 1.493938 0.585344 1.256628 0.045 Uiso 1 1 calc R U . . .
C6 C 1.0048(7) 0.2583(6) 0.7242(4) 0.0298(12) Uani 1 1 d . . . . .
C14 C 0.7558(6) 0.0490(6) 1.0897(4) 0.0252(11) Uani 1 1 d . . . . .
C1 C 0.8606(7) 0.1241(6) 0.7299(4) 0.0295(12) Uani 1 1 d . . . . .
C2 C 0.7393(7) 0.0162(6) 0.6195(4) 0.0331(12) Uani 1 1 d . . . . .
H2A H 0.642306 -0.071633 0.620083 0.040 Uiso 1 1 calc R U . . .
C7 C 1.1326(6) 0.3810(6) 0.8287(4) 0.0270(11) Uani 1 1 d . . . . .
H7 H 1.216025 0.471569 0.817248 0.032 Uiso 1 1 calc R U . . .
C15 C 0.6591(7) -0.0785(6) 1.1448(5) 0.0377(13) Uani 1 1 d . . . . .
H15A H 0.726434 -0.057442 1.225358 0.057 Uiso 1 1 calc R U . . .
H15B H 0.636569 -0.191029 1.097555 0.057 Uiso 1 1 calc R U . . .
H15C H 0.552508 -0.068393 1.146765 0.057 Uiso 1 1 calc R U . . .
C12 C 1.2839(7) 0.4130(6) 1.3726(4) 0.0358(13) Uani 1 1 d . . . . .
H12A H 1.247288 0.401912 1.443751 0.043 Uiso 1 1 calc R U . . .
H12B H 1.374297 0.370977 1.372836 0.043 Uiso 1 1 calc R U . . .
C9 C 1.2445(7) 0.5040(7) 1.1522(5) 0.0378(13) Uani 1 1 d . . . . .
H9 H 1.152621 0.544735 1.155935 0.045 Uiso 1 1 calc R U . . .
C4 C 0.9032(8) 0.1665(8) 0.5059(5) 0.0507(16) Uani 1 1 d . . . . .
H4 H 0.917520 0.178607 0.432143 0.061 Uiso 1 1 calc R U . . .
C11 C 1.3538(8) 0.5971(7) 1.3781(5) 0.0417(14) Uani 1 1 d . . . . .
H11A H 1.455983 0.659323 1.446049 0.050 Uiso 1 1 calc R U . . .
H11B H 1.269411 0.644273 1.389503 0.050 Uiso 1 1 calc R U . . .
C5 C 1.0216(7) 0.2752(7) 0.6116(5) 0.0397(13) Uani 1 1 d . . . . .
H5 H 1.116452 0.363329 0.608758 0.048 Uiso 1 1 calc R U . . .
C3 C 0.7603(8) 0.0369(7) 0.5121(5) 0.0444(15) Uani 1 1 d . . . . .
H3 H 0.677364 -0.037067 0.441189 0.053 Uiso 1 1 calc R U . . .
O4 O 0.4627(5) 0.2046(4) 0.1877(3) 0.0440(10) Uani 1 1 d . . . . .
H1O4 H 0.549846 0.184509 0.178700 0.066 Uiso 1 1 d R U . . .
H2O4 H 0.381325 0.109829 0.175970 0.066 Uiso 1 1 d 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 1.928(3) . ?
Cu1 N1 1.941(4) . ?
Cu1 O2 1.951(3) . ?
Cu1 N2 2.026(4) . ?
O2 C14 1.280(5) . ?
O3 C14 1.239(5) . ?
O1 C1 1.313(5) . ?
N1 C7 1.284(6) . ?
N1 C8 1.469(6) . ?
C8 C9 1.487(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N2 C13 1.470(6) . ?
N2 C9 1.484(6) . ?
N2 H2 0.9800 . ?
C13 C12 1.511(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C10 C9 1.523(7) . ?
C10 C11 1.529(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C6 C5 1.404(7) . ?
C6 C1 1.421(7) . ?
C6 C7 1.421(7) . ?
C14 C15 1.504(6) . ?
C1 C2 1.409(7) . ?
C2 C3 1.362(7) . ?
C2 H2A 0.9300 . ?
C7 H7 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C12 C11 1.501(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9 H9 0.9800 . ?
C4 C5 1.366(8) . ?
C4 C3 1.395(8) . ?
C4 H4 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
O4 H1O4 0.8515 . ?
O4 H2O4 0.8505 . ?

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 N1 91.90(15) . . ?
O1 Cu1 O2 90.76(13) . . ?
N1 Cu1 O2 177.13(15) . . ?
O1 Cu1 N2 172.76(14) . . ?
N1 Cu1 N2 83.31(16) . . ?
O2 Cu1 N2 93.94(14) . . ?
C14 O2 Cu1 114.2(3) . . ?
C1 O1 Cu1 125.8(3) . . ?
C7 N1 C8 119.4(4) . . ?
C7 N1 Cu1 125.9(3) . . ?
C8 N1 Cu1 114.2(3) . . ?
N1 C8 C9 108.8(4) . . ?
N1 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C13 N2 C9 110.9(4) . . ?
C13 N2 Cu1 121.4(3) . . ?
C9 N2 Cu1 106.1(3) . . ?
C13 N2 H2 105.8 . . ?
C9 N2 H2 105.8 . . ?
Cu1 N2 H2 105.8 . . ?
N2 C13 C12 112.4(4) . . ?
N2 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
N2 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C9 C10 C11 110.8(5) . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C5 C6 C1 119.5(5) . . ?
C5 C6 C7 117.8(5) . . ?
C1 C6 C7 122.7(4) . . ?
O3 C14 O2 123.3(4) . . ?
O3 C14 C15 120.8(4) . . ?
O2 C14 C15 115.9(4) . . ?
O1 C1 C2 119.0(5) . . ?
O1 C1 C6 124.2(5) . . ?
C2 C1 C6 116.8(4) . . ?
C3 C2 C1 121.8(5) . . ?
C3 C2 H2A 119.1 . . ?
C1 C2 H2A 119.1 . . ?
N1 C7 C6 125.6(5) . . ?
N1 C7 H7 117.2 . . ?
C6 C7 H7 117.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C12 C13 112.3(4) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
N2 C9 C8 108.2(4) . . ?
N2 C9 C10 112.8(4) . . ?
C8 C9 C10 112.6(5) . . ?
N2 C9 H9 107.7 . . ?
C8 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
C5 C4 C3 118.0(5) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C12 C11 C10 110.1(4) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.2 . . ?
C4 C5 C6 122.3(5) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C2 C3 C4 121.5(5) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
H1O4 O4 H2O4 107.5 . . ?

_refine_diff_density_max         0.628
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.106

