# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_Ela-15
_database_code_depnum_ccdc_archive 'CCDC 1555645'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H40 Cu2 N4 O6'
_chemical_formula_sum            'C22 H40 Cu2 N4 O6'
_chemical_formula_weight         583.66

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                   11.0854(10)
_cell_length_b                   10.0289(5)
_cell_length_c                   11.5267(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.229(8)
_cell_angle_gamma                90
_cell_volume                     1264.89(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    115.00(10)
_cell_measurement_reflns_used    1389
_cell_measurement_theta_min      4.1190
_cell_measurement_theta_max      27.8330

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.725
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.59111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      115.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4887
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.119
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2221
_reflns_number_gt                1745
_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       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_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)+(0.0494P)²] 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         2221
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.1222(3) 0.1950(3) 1.0015(3) 0.0236(7) Uani 1 1 d . . . . .
H1A H 0.0898 0.2206 0.9224 0.035 Uiso 1 1 calc R U . . .
H1B H 0.0776 0.2395 1.0551 0.035 Uiso 1 1 calc R U . . .
H1C H 0.1146 0.1003 1.0098 0.035 Uiso 1 1 calc R U . . .
C2 C 0.2543(3) 0.2335(3) 1.0286(3) 0.0202(7) Uani 1 1 d . . . . .
C3 C 0.2906(3) 0.3273(2) 1.1138(3) 0.0216(7) Uani 1 1 d . . . . .
H3 H 0.2309 0.3590 1.1550 0.026 Uiso 1 1 calc R U . . .
C4 C 0.4090(3) 0.3804(3) 1.1452(2) 0.0199(7) Uani 1 1 d . . . . .
C5 C 0.4262(3) 0.4918(2) 1.2340(3) 0.0247(7) Uani 1 1 d . . . . .
H5A H 0.4816 0.4637 1.3023 0.037 Uiso 1 1 calc R U . . .
H5B H 0.3488 0.5143 1.2561 0.037 Uiso 1 1 calc R U . . .
H5C H 0.4590 0.5685 1.2002 0.037 Uiso 1 1 calc R U . . .
C6 C 0.6238(3) 0.3985(3) 1.1344(3) 0.0239(7) Uani 1 1 d . . . . .
H6A H 0.6566 0.3754 1.2150 0.029 Uiso 1 1 calc R U . . .
H6B H 0.6168 0.4948 1.1287 0.029 Uiso 1 1 calc R U . . .
C7 C 0.7067(3) 0.3476(3) 1.0527(3) 0.0228(7) Uani 1 1 d . . . . .
H7A H 0.6885 0.3934 0.9778 0.027 Uiso 1 1 calc R U . . .
H7B H 0.7911 0.3660 1.0860 0.027 Uiso 1 1 calc R U . . .
C8 C 0.7415(3) 0.1292(3) 1.1418(3) 0.0261(7) Uani 1 1 d . . . . .
H8A H 0.8271 0.1488 1.1616 0.039 Uiso 1 1 calc R U . . .
H8B H 0.7306 0.0351 1.1285 0.039 Uiso 1 1 calc R U . . .
H8C H 0.7004 0.1559 1.2053 0.039 Uiso 1 1 calc R U . . .
C9 C 0.7560(3) 0.1617(3) 0.9392(3) 0.0261(7) Uani 1 1 d . . . . .
H9A H 0.7254 0.2107 0.8691 0.039 Uiso 1 1 calc R U . . .
H9B H 0.7442 0.0680 0.9245 0.039 Uiso 1 1 calc R U . . .
H9C H 0.8416 0.1797 0.9618 0.039 Uiso 1 1 calc R U . . .
C10 C 0.5064(3) 0.0696(3) 0.7814(3) 0.0204(7) Uani 1 1 d . . . . .
C11 C 0.5135(3) -0.0399(3) 0.6939(3) 0.0290(8) Uani 1 1 d . . . . .
H11A H 0.4324 -0.0664 0.6594 0.043 Uiso 1 1 calc R U . . .
H11B H 0.5559 -0.1149 0.7329 0.043 Uiso 1 1 calc R U . . .
H11C H 0.5567 -0.0085 0.6334 0.043 Uiso 1 1 calc R U . . .
N1 N 0.5032(2) 0.3363(2) 1.0996(2) 0.0199(6) Uani 1 1 d . . . . .
N2 N 0.6899(2) 0.2025(2) 1.0343(2) 0.0184(6) Uani 1 1 d . . . . .
O1 O 0.32510(19) 0.17480(16) 0.96592(18) 0.0208(5) Uani 1 1 d . . . . .
O2 O 0.50804(18) 0.03220(18) 0.88810(17) 0.0186(5) Uani 1 1 d . . . . .
O3 O 0.5011(2) 0.18761(16) 0.74945(19) 0.0256(5) Uani 1 1 d . . . . .
Cu1 Cu 0.50203(3) 0.17963(3) 0.99904(3) 0.01706(15) 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 1.498(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.291(4) . ?
C2 C3 1.373(4) . ?
C3 C4 1.409(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.319(4) . ?
C4 C5 1.507(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N1 1.471(4) . ?
C6 C7 1.507(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.478(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.475(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N2 1.472(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O3 1.237(3) . ?
C10 O2 1.284(3) . ?
C10 C11 1.502(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N1 Cu1 1.951(2) . ?
N2 Cu1 2.070(2) . ?
O1 Cu1 1.938(2) . ?
O2 Cu1 1.9630(19) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 125.3(3) . . ?
O1 C2 C1 115.3(2) . . ?
C3 C2 C1 119.3(3) . . ?
C2 C3 C4 126.7(3) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
N1 C4 C3 122.4(3) . . ?
N1 C4 C5 119.8(3) . . ?
C3 C4 C5 117.8(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C7 107.7(2) . . ?
N1 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
N1 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
N2 C7 C6 110.3(2) . . ?
N2 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 O2 123.9(3) . . ?
O3 C10 C11 120.3(3) . . ?
O2 C10 C11 115.8(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 N1 C6 119.5(2) . . ?
C4 N1 Cu1 125.2(2) . . ?
C6 N1 Cu1 114.99(19) . . ?
C9 N2 C8 108.3(2) . . ?
C9 N2 C7 108.3(2) . . ?
C8 N2 C7 110.3(2) . . ?
C9 N2 Cu1 115.37(18) . . ?
C8 N2 Cu1 110.62(19) . . ?
C7 N2 Cu1 103.72(17) . . ?
C2 O1 Cu1 124.43(18) . . ?
C10 O2 Cu1 114.03(17) . . ?
O1 Cu1 N1 92.70(9) . . ?
O1 Cu1 O2 89.53(8) . . ?
N1 Cu1 O2 174.75(9) . . ?
O1 Cu1 N2 175.07(8) . . ?
N1 Cu1 N2 83.31(10) . . ?
O2 Cu1 N2 94.20(9) . . ?

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 C2 C3 C4 2.7(5) . . . . ?
C1 C2 C3 C4 -176.0(3) . . . . ?
C2 C3 C4 N1 -5.2(5) . . . . ?
C2 C3 C4 C5 174.6(3) . . . . ?
N1 C6 C7 N2 -43.2(3) . . . . ?
C3 C4 N1 C6 178.6(3) . . . . ?
C5 C4 N1 C6 -1.2(4) . . . . ?
C3 C4 N1 Cu1 -8.2(4) . . . . ?
C5 C4 N1 Cu1 172.04(19) . . . . ?
C7 C6 N1 C4 -169.2(2) . . . . ?
C7 C6 N1 Cu1 16.9(3) . . . . ?
C6 C7 N2 C9 170.4(2) . . . . ?
C6 C7 N2 C8 -71.2(3) . . . . ?
C6 C7 N2 Cu1 47.3(3) . . . . ?
C3 C2 O1 Cu1 12.8(4) . . . . ?
C1 C2 O1 Cu1 -168.42(17) . . . . ?
O3 C10 O2 Cu1 -0.2(4) . . . . ?
C11 C10 O2 Cu1 178.8(2) . . . . ?

_refine_diff_density_max         0.493
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.081

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_Ela-16
_database_code_depnum_ccdc_archive 'CCDC 1555646'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H46 Cu2 N4 O7'
_chemical_formula_weight         725.81

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           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

_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, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   12.9343(7)
_cell_length_b                   9.8945(4)
_cell_length_c                   13.0557(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.231(4)
_cell_angle_gamma                90
_cell_volume                     1669.58(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    115.00(10)
_cell_measurement_reflns_used    2208
_cell_measurement_theta_min      3.7220
_cell_measurement_theta_max      27.4190

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.325
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.80333
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      115.00(10)
_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  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6711
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.995
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2940
_reflns_number_gt                2491
_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       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_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)+(0.0326P)²+0.4745P] 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         2940
_refine_ls_number_parameters     210
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0706
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.022
_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 1.29448(18) 0.2349(2) -0.10776(18) 0.0178(5) Uani 1 1 d . . . . .
H1 H 1.2418 0.2576 -0.1551 0.021 Uiso 1 1 calc R U . . .
C2 C 1.39595(18) 0.2396(2) -0.13652(19) 0.0205(5) Uani 1 1 d . . . . .
H2 H 1.4114 0.2662 -0.2025 0.025 Uiso 1 1 calc R U . . .
C3 C 1.47476(19) 0.2046(2) -0.0666(2) 0.0244(6) Uani 1 1 d . . . . .
H3 H 1.5433 0.2079 -0.0854 0.029 Uiso 1 1 calc R U . . .
C4 C 1.45106(19) 0.1649(2) 0.0310(2) 0.0277(6) Uani 1 1 d . . . . .
H4 H 1.5039 0.1405 0.0777 0.033 Uiso 1 1 calc R U . . .
C5 C 1.34926(19) 0.1609(2) 0.06001(19) 0.0221(5) Uani 1 1 d . . . . .
H5 H 1.3342 0.1342 0.1261 0.027 Uiso 1 1 calc R U . . .
C6 C 1.26958(17) 0.1965(2) -0.00897(18) 0.0148(5) Uani 1 1 d . . . . .
C7 C 1.15816(18) 0.1985(2) 0.01866(18) 0.0151(5) Uani 1 1 d . . . . .
C8 C 1.12469(18) 0.1152(2) 0.09524(18) 0.0170(5) Uani 1 1 d . . . . .
H8 H 1.1748 0.0665 0.1326 0.020 Uiso 1 1 calc R U . . .
C9 C 1.02087(18) 0.0975(2) 0.12169(17) 0.0158(5) Uani 1 1 d . . . . .
C10 C 0.99907(18) -0.0132(2) 0.19654(19) 0.0211(5) Uani 1 1 d . . . . .
H10A H 0.9513 0.0189 0.2454 0.032 Uiso 1 1 calc R U . . .
H10B H 1.0624 -0.0399 0.2317 0.032 Uiso 1 1 calc R U . . .
H10C H 0.9696 -0.0893 0.1604 0.032 Uiso 1 1 calc R U . . .
C11 C 0.83895(17) 0.1398(2) 0.10792(19) 0.0190(5) Uani 1 1 d . . . . .
H11A H 0.8279 0.1645 0.1786 0.023 Uiso 1 1 calc R U . . .
H11B H 0.8258 0.0438 0.0999 0.023 Uiso 1 1 calc R U . . .
C12 C 0.76727(18) 0.2197(2) 0.03663(19) 0.0186(5) Uani 1 1 d . . . . .
H12A H 0.7629 0.1765 -0.0301 0.022 Uiso 1 1 calc R U . . .
H12B H 0.6984 0.2215 0.0636 0.022 Uiso 1 1 calc R U . . .
C13 C 0.80016(18) 0.4327(2) 0.12413(17) 0.0173(5) Uani 1 1 d . . . . .
H13A H 0.8420 0.3871 0.1758 0.026 Uiso 1 1 calc R U . . .
H13B H 0.7296 0.4347 0.1443 0.026 Uiso 1 1 calc R U . . .
H13C H 0.8248 0.5234 0.1163 0.026 Uiso 1 1 calc R U . . .
C14 C 0.74168(18) 0.4325(2) -0.05162(18) 0.0201(5) Uani 1 1 d . . . . .
H14A H 0.7447 0.3866 -0.1162 0.030 Uiso 1 1 calc R U . . .
H14B H 0.7668 0.5232 -0.0585 0.030 Uiso 1 1 calc R U . . .
H14C H 0.6714 0.4348 -0.0306 0.030 Uiso 1 1 calc R U . . .
C15 C 1.06028(17) 0.5469(2) 0.19174(18) 0.0161(5) Uani 1 1 d . . . . .
C16 C 1.0585(2) 0.4335(2) 0.26859(19) 0.0274(6) Uani 1 1 d . . . . .
H16A H 1.1280 0.4109 0.2905 0.041 Uiso 1 1 calc R U . . .
H16B H 1.0256 0.3558 0.2376 0.041 Uiso 1 1 calc R U . . .
H16C H 1.0206 0.4615 0.3267 0.041 Uiso 1 1 calc R U . . .
N1 N 0.80637(14) 0.36013(17) 0.02608(14) 0.0153(4) Uani 1 1 d . . . . .
N2 N 0.94493(14) 0.17096(17) 0.08170(14) 0.0152(4) Uani 1 1 d . . . . .
O1 O 1.10047(11) 0.27974(15) -0.03556(12) 0.0167(4) Uani 1 1 d . . . . .
O2 O 1.03208(11) 0.51737(14) 0.09891(11) 0.0150(3) Uani 1 1 d . . . . .
O3 O 1.08891(12) 0.66119(14) 0.21907(12) 0.0201(4) Uani 1 1 d D . . . .
O4 O 1.2500 0.8507(2) 0.2500 0.0313(6) Uani 1 2 d DS T P . .
Cu1 Cu 0.96045(2) 0.32839(2) -0.00505(2) 0.01322(10) Uani 1 1 d . . . . .
H1O4 H 1.1971(17) 0.797(2) 0.239(3) 0.058(10) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.380(3) . ?
C1 C6 1.394(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.499(3) . ?
C7 O1 1.289(3) . ?
C7 C8 1.379(3) . ?
C8 C9 1.410(3) . ?
C8 H8 0.9300 . ?
C9 N2 1.313(3) . ?
C9 C10 1.502(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N2 1.459(3) . ?
C11 C12 1.511(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N1 1.487(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N1 1.472(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N1 1.475(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O3 1.238(3) . ?
C15 O2 1.286(3) . ?
C15 C16 1.506(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 Cu1 2.0732(19) . ?
N2 Cu1 1.9409(18) . ?
O1 Cu1 1.9305(15) . ?
O2 Cu1 1.9620(15) 3_765 ?
O4 H1O4 0.876(13) . ?
Cu1 O2 1.9620(15) 3_765 ?

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 C6 121.2(2) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 C7 122.9(2) . . ?
C1 C6 C7 118.6(2) . . ?
O1 C7 C8 125.4(2) . . ?
O1 C7 C6 114.66(19) . . ?
C8 C7 C6 119.9(2) . . ?
C7 C8 C9 125.5(2) . . ?
C7 C8 H8 117.3 . . ?
C9 C8 H8 117.3 . . ?
N2 C9 C8 122.6(2) . . ?
N2 C9 C10 120.4(2) . . ?
C8 C9 C10 117.0(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 107.74(18) . . ?
N2 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
N2 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
N1 C12 C11 110.06(18) . . ?
N1 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
N1 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
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 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O2 123.4(2) . . ?
O3 C15 C16 120.1(2) . . ?
O2 C15 C16 116.59(19) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 N1 C14 108.22(17) . . ?
C13 N1 C12 110.16(17) . . ?
C14 N1 C12 109.36(17) . . ?
C13 N1 Cu1 109.25(14) . . ?
C14 N1 Cu1 117.55(14) . . ?
C12 N1 Cu1 102.10(13) . . ?
C9 N2 C11 119.01(18) . . ?
C9 N2 Cu1 125.67(15) . . ?
C11 N2 Cu1 115.21(14) . . ?
C7 O1 Cu1 124.73(14) . . ?
C15 O2 Cu1 113.14(13) . 3_765 ?
O1 Cu1 N2 92.26(7) . . ?
O1 Cu1 O2 89.75(6) . 3_765 ?
N2 Cu1 O2 175.93(7) . 3_765 ?
O1 Cu1 N1 174.21(6) . . ?
N2 Cu1 N1 83.41(7) . . ?
O2 Cu1 N1 94.34(6) 3_765 . ?

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 0.6(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 -178.0(2) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C1 C6 C7 177.68(19) . . . . ?
C5 C6 C7 O1 154.3(2) . . . . ?
C1 C6 C7 O1 -24.3(3) . . . . ?
C5 C6 C7 C8 -27.1(3) . . . . ?
C1 C6 C7 C8 154.2(2) . . . . ?
O1 C7 C8 C9 5.0(4) . . . . ?
C6 C7 C8 C9 -173.4(2) . . . . ?
C7 C8 C9 N2 -7.2(4) . . . . ?
C7 C8 C9 C10 171.1(2) . . . . ?
N2 C11 C12 N1 -43.4(2) . . . . ?
C11 C12 N1 C13 -66.9(2) . . . . ?
C11 C12 N1 C14 174.28(18) . . . . ?
C11 C12 N1 Cu1 49.1(2) . . . . ?
C8 C9 N2 C11 175.8(2) . . . . ?
C10 C9 N2 C11 -2.4(3) . . . . ?
C8 C9 N2 Cu1 -8.3(3) . . . . ?
C10 C9 N2 Cu1 173.56(15) . . . . ?
C12 C11 N2 C9 -169.05(19) . . . . ?
C12 C11 N2 Cu1 14.6(2) . . . . ?
C8 C7 O1 Cu1 12.4(3) . . . . ?
C6 C7 O1 Cu1 -169.14(13) . . . . ?
O3 C15 O2 Cu1 0.2(3) . . . 3_765 ?
C16 C15 O2 Cu1 -179.06(16) . . . 3_765 ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_Ela-18
_database_code_depnum_ccdc_archive 'CCDC 1555647'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H34 Cu2 N2 O8'
_chemical_formula_sum            'C20 H34 Cu2 N2 O8'
_chemical_formula_weight         557.57

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                   8.8928(3)
_cell_length_b                   7.2198(2)
_cell_length_c                   18.5441(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.554(3)
_cell_angle_gamma                90
_cell_volume                     1190.17(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    115.5(4)
_cell_measurement_reflns_used    2378
_cell_measurement_theta_min      3.5690
_cell_measurement_theta_max      27.8470

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             580
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    1.833
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.93514
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      115.5(4)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4581
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.132
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2093
_reflns_number_gt                1653
_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       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_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)+(0.0309P)²+0.0264P] 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         2093
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0673
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.6581(3) -0.2650(4) 0.27343(13) 0.0259(7) Uani 1 1 d . . . . .
H1A H 0.6842 -0.3873 0.2898 0.039 Uiso 1 1 calc R U . . .
H1B H 0.7094 -0.2384 0.2297 0.039 Uiso 1 1 calc R U . . .
H1C H 0.5514 -0.2579 0.2645 0.039 Uiso 1 1 calc R U . . .
C2 C 0.7037(3) -0.1263(4) 0.33022(13) 0.0195(6) Uani 1 1 d . . . . .
C3 C 0.7932(3) 0.0211(4) 0.31199(14) 0.0194(6) Uani 1 1 d . . . . .
H3 H 0.8196 0.0297 0.2639 0.023 Uiso 1 1 calc R U . . .
C4 C 0.8491(3) 0.1607(4) 0.35900(13) 0.0174(6) Uani 1 1 d . . . . .
C5 C 0.9452(3) 0.3102(4) 0.32691(13) 0.0256(6) Uani 1 1 d . . . . .
H5A H 0.9004 0.4290 0.3353 0.038 Uiso 1 1 calc R U . . .
H5B H 0.9522 0.2901 0.2759 0.038 Uiso 1 1 calc R U . . .
H5C H 1.0440 0.3065 0.3490 0.038 Uiso 1 1 calc R U . . .
C6 C 0.8817(3) 0.3107(4) 0.47408(13) 0.0196(6) Uani 1 1 d . . . . .
H6A H 0.8183 0.4197 0.4699 0.023 Uiso 1 1 calc R U . . .
H6B H 0.9819 0.3436 0.4592 0.023 Uiso 1 1 calc R U . . .
C7 C 0.8871(3) 0.2428(4) 0.55086(13) 0.0205(6) Uani 1 1 d . . . . .
H7A H 0.9661 0.1514 0.5577 0.025 Uiso 1 1 calc R U . . .
H7B H 0.9063 0.3449 0.5838 0.025 Uiso 1 1 calc R U . . .
C8 C 0.7271(3) 0.1062(4) 0.63686(12) 0.0227(6) Uani 1 1 d . . . . .
H8A H 0.8019 0.0146 0.6490 0.034 Uiso 1 1 calc R U . . .
H8B H 0.6288 0.0549 0.6431 0.034 Uiso 1 1 calc R U . . .
H8C H 0.7405 0.2119 0.6678 0.034 Uiso 1 1 calc R U . . .
C9 C 0.6190(3) -0.2914(4) 0.56286(12) 0.0168(6) Uani 1 1 d . . . . .
C10 C 0.5214(3) -0.4284(4) 0.60008(14) 0.0265(6) Uani 1 1 d . . . . .
H10A H 0.4882 -0.5215 0.5663 0.040 Uiso 1 1 calc R U . . .
H10B H 0.4356 -0.3659 0.6189 0.040 Uiso 1 1 calc R U . . .
H10C H 0.5777 -0.4857 0.6389 0.040 Uiso 1 1 calc R U . . .
N1 N 0.8206(2) 0.1620(3) 0.42802(10) 0.0160(5) Uani 1 1 d . . . . .
O1 O 0.65263(19) -0.1583(2) 0.39308(8) 0.0218(4) Uani 1 1 d . . . . .
O2 O 0.74239(18) 0.1616(2) 0.56352(8) 0.0171(4) Uani 1 1 d . . . . .
O3 O 0.55086(17) -0.1548(2) 0.53128(8) 0.0149(4) Uani 1 1 d . . . . .
O4 O 0.75707(19) -0.3112(3) 0.56240(9) 0.0257(4) Uani 1 1 d . . . . .
Cu1 Cu 0.68077(3) 0.00165(4) 0.47485(2) 0.01435(12) 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 1.501(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.283(3) . ?
C2 C3 1.377(4) . ?
C3 C4 1.414(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.312(3) . ?
C4 C5 1.509(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N1 1.467(3) . ?
C6 C7 1.505(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O2 1.439(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O2 1.428(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O4 1.237(3) . ?
C9 O3 1.290(3) . ?
C9 C10 1.497(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 Cu1 1.9230(19) . ?
O1 Cu1 1.9171(17) . ?
O2 Cu1 2.0710(16) . ?
O3 Cu1 1.9418(15) . ?
O3 Cu1 2.3379(16) 3_656 ?
Cu1 O3 2.3379(16) 3_656 ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 125.7(2) . . ?
O1 C2 C1 114.9(2) . . ?
C3 C2 C1 119.4(2) . . ?
C2 C3 C4 126.6(2) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
N1 C4 C3 122.2(2) . . ?
N1 C4 C5 120.4(2) . . ?
C3 C4 C5 117.4(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C7 108.3(2) . . ?
N1 C6 H6A 110.0 . . ?
C7 C6 H6A 110.0 . . ?
N1 C6 H6B 110.0 . . ?
C7 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
O2 C7 C6 106.33(19) . . ?
O2 C7 H7A 110.5 . . ?
C6 C7 H7A 110.5 . . ?
O2 C7 H7B 110.5 . . ?
C6 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 O3 122.7(2) . . ?
O4 C9 C10 121.0(2) . . ?
O3 C9 C10 116.3(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 N1 C6 119.7(2) . . ?
C4 N1 Cu1 125.52(18) . . ?
C6 N1 Cu1 114.29(14) . . ?
C2 O1 Cu1 124.61(16) . . ?
C8 O2 C7 112.21(18) . . ?
C8 O2 Cu1 124.77(15) . . ?
C7 O2 Cu1 108.43(12) . . ?
C9 O3 Cu1 114.23(15) . . ?
C9 O3 Cu1 141.82(15) . 3_656 ?
Cu1 O3 Cu1 103.60(7) . 3_656 ?
O1 Cu1 N1 94.45(8) . . ?
O1 Cu1 O3 90.52(7) . . ?
N1 Cu1 O3 174.14(8) . . ?
O1 Cu1 O2 171.90(7) . . ?
N1 Cu1 O2 82.09(7) . . ?
O3 Cu1 O2 92.58(6) . . ?
O1 Cu1 O3 98.66(7) . 3_656 ?
N1 Cu1 O3 105.84(7) . 3_656 ?
O3 Cu1 O3 76.40(7) . 3_656 ?
O2 Cu1 O3 89.35(6) . 3_656 ?

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 C2 C3 C4 2.1(4) . . . . ?
C1 C2 C3 C4 -178.3(2) . . . . ?
C2 C3 C4 N1 0.6(4) . . . . ?
C2 C3 C4 C5 -179.8(3) . . . . ?
N1 C6 C7 O2 -48.0(3) . . . . ?
C3 C4 N1 C6 -180.0(2) . . . . ?
C5 C4 N1 C6 0.4(3) . . . . ?
C3 C4 N1 Cu1 -8.8(3) . . . . ?
C5 C4 N1 Cu1 171.64(17) . . . . ?
C7 C6 N1 C4 -157.7(2) . . . . ?
C7 C6 N1 Cu1 30.2(2) . . . . ?
C3 C2 O1 Cu1 3.7(4) . . . . ?
C1 C2 O1 Cu1 -175.86(16) . . . . ?
C6 C7 O2 C8 -174.6(2) . . . . ?
C6 C7 O2 Cu1 43.6(2) . . . . ?
O4 C9 O3 Cu1 6.1(3) . . . . ?
C10 C9 O3 Cu1 -173.25(16) . . . . ?
O4 C9 O3 Cu1 -165.59(17) . . . 3_656 ?
C10 C9 O3 Cu1 15.1(4) . . . 3_656 ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_Ela-17
_database_code_depnum_ccdc_archive 'CCDC 1555648'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H24 Cu N2 O3), H2 O'
_chemical_formula_sum            'C26 H50 Cu2 N4 O7'
_chemical_formula_weight         657.78

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                   22.4102(19)
_cell_length_b                   12.7485(9)
_cell_length_c                   11.2535(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.524(7)
_cell_angle_gamma                90
_cell_volume                     3205.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    116(1)
_cell_measurement_reflns_used    2097
_cell_measurement_theta_min      3.6560
_cell_measurement_theta_max      26.1740

_exptl_crystal_description       blue
_exptl_crystal_colour            plate
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.372
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.40287
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      116(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10414
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.168
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        25.000
_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             2816
_reflns_number_gt                2074
_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       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_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)+(0.0462P)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         2816
_refine_ls_number_parameters     236
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_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 0.29636(16) 0.0430(3) 0.8799(3) 0.0318(9) Uani 1 1 d . . . . .
H1A H 0.3250 0.0951 0.8606 0.048 Uiso 1 1 calc R U . . .
H1B H 0.3154 -0.0245 0.8857 0.048 Uiso 1 1 calc R U . . .
H1C H 0.2810 0.0602 0.9548 0.048 Uiso 1 1 calc R U . . .
C2 C 0.24574(16) 0.0402(3) 0.7841(3) 0.0241(8) Uani 1 1 d . . . . .
C3 C 0.23403(16) -0.0499(3) 0.7195(3) 0.0246(8) Uani 1 1 d . . . . .
H3 H 0.2582 -0.1076 0.7397 0.029 Uiso 1 1 calc R U . . .
C4 C 0.18913(16) -0.0640(3) 0.6257(3) 0.0236(8) Uani 1 1 d . . . . .
C5 C 0.18413(17) -0.1723(3) 0.5696(3) 0.0307(9) Uani 1 1 d . . . . .
H5A H 0.1446 -0.1996 0.5766 0.046 Uiso 1 1 calc R U . . .
H5B H 0.2131 -0.2182 0.6097 0.046 Uiso 1 1 calc R U . . .
H5C H 0.1915 -0.1675 0.4868 0.046 Uiso 1 1 calc R U . . .
C6 C 0.10905(17) -0.0062(3) 0.4858(3) 0.0325(9) Uani 1 1 d . . . . .
H6A H 0.0901 -0.0739 0.4940 0.039 Uiso 0.55 1 calc R U P A 1
H6B H 0.1289 -0.0064 0.4123 0.039 Uiso 0.55 1 calc R U P A 1
H6C H 0.0698 -0.0190 0.5135 0.039 Uiso 0.45 1 calc R U P B 2
H6D H 0.1203 -0.0662 0.4395 0.039 Uiso 0.45 1 calc R U P B 2
C7 C 0.0626(3) 0.0783(5) 0.4811(6) 0.0318(17) Uani 0.55 1 d . . P C 1
H7A H 0.0365 0.0698 0.5453 0.038 Uiso 0.55 1 calc R U P C 1
H7B H 0.0385 0.0764 0.4057 0.038 Uiso 0.55 1 calc R U P C 1
C7' C 0.1086(4) 0.0988(6) 0.4070(6) 0.0251(19) Uani 0.45 1 d . . P C 2
H7'1 H 0.1465 0.1083 0.3723 0.030 Uiso 0.45 1 calc R U P C 2
H7'2 H 0.0767 0.0969 0.3435 0.030 Uiso 0.45 1 calc R U P C 2
C8 C 0.1312(3) 0.2047(6) 0.4021(6) 0.0321(17) Uani 0.55 1 d . . P C 1
H8A H 0.1050 0.2068 0.3294 0.038 Uiso 0.55 1 calc R U P C 1
H8B H 0.1593 0.1475 0.3950 0.038 Uiso 0.55 1 calc R U P C 1
C9 C 0.1653(5) 0.3057(10) 0.4143(11) 0.033(3) Uani 0.55 1 d . . P C 1
H9A H 0.1377 0.3634 0.4121 0.049 Uiso 0.55 1 calc R U P C 1
H9B H 0.1907 0.3122 0.3498 0.049 Uiso 0.55 1 calc R U P C 1
H9C H 0.1894 0.3063 0.4887 0.049 Uiso 0.55 1 calc R U P C 1
C10 C 0.0493(4) 0.2654(7) 0.5170(7) 0.032(2) Uani 0.55 1 d . . P C 1
H10A H 0.0263 0.2395 0.5805 0.038 Uiso 0.55 1 calc R U P C 1
H10B H 0.0682 0.3304 0.5442 0.038 Uiso 0.55 1 calc R U P C 1
C11 C 0.0066(5) 0.2885(8) 0.4086(8) 0.039(2) Uani 0.55 1 d . . P C 1
H11A H 0.0286 0.3161 0.3459 0.059 Uiso 0.55 1 calc R U P C 1
H11B H -0.0226 0.3390 0.4294 0.059 Uiso 0.55 1 calc R U P C 1
H11C H -0.0133 0.2250 0.3821 0.059 Uiso 0.55 1 calc R U P C 1
C8' C 0.1249(4) 0.2887(7) 0.4321(7) 0.0229(19) Uani 0.45 1 d . . P C 2
H8'1 H 0.1089 0.2905 0.3495 0.027 Uiso 0.45 1 calc R U P C 2
H8'2 H 0.1104 0.3506 0.4709 0.027 Uiso 0.45 1 calc R U P C 2
C9' C 0.1935(5) 0.2949(13) 0.4356(14) 0.035(3) Uani 0.45 1 d . . P C 2
H9'1 H 0.2100 0.2961 0.5169 0.052 Uiso 0.45 1 calc R U P C 2
H9'2 H 0.2049 0.3576 0.3959 0.052 Uiso 0.45 1 calc R U P C 2
H9'3 H 0.2085 0.2348 0.3960 0.052 Uiso 0.45 1 calc R U P C 2
C10' C 0.0396(4) 0.2045(8) 0.5164(8) 0.023(2) Uani 0.45 1 d . . P C 2
H10C H 0.0397 0.2624 0.5723 0.027 Uiso 0.45 1 calc R U P C 2
H10D H 0.0253 0.1434 0.5570 0.027 Uiso 0.45 1 calc R U P C 2
C11' C -0.0068(5) 0.2299(9) 0.4144(10) 0.034(3) Uani 0.45 1 d . . P C 2
H11D H 0.0049 0.2922 0.3744 0.051 Uiso 0.45 1 calc R U P C 2
H11E H -0.0450 0.2410 0.4454 0.051 Uiso 0.45 1 calc R U P C 2
H11F H -0.0096 0.1725 0.3590 0.051 Uiso 0.45 1 calc R U P C 2
C12 C 0.10727(17) 0.2959(3) 0.7897(3) 0.0253(8) Uani 1 1 d . . . . .
C13 C 0.09700(19) 0.4035(3) 0.8422(3) 0.0417(11) Uani 1 1 d . . . . .
H13A H 0.0685 0.4414 0.7905 0.063 Uiso 1 1 calc R U . . .
H13B H 0.1341 0.4414 0.8500 0.063 Uiso 1 1 calc R U . . .
H13C H 0.0819 0.3957 0.9192 0.063 Uiso 1 1 calc R U . . .
N1 N 0.15317(13) 0.0115(2) 0.5869(2) 0.0247(7) Uani 1 1 d . . . . .
N2 N 0.09819(14) 0.1853(2) 0.4951(2) 0.0286(8) Uani 1 1 d . . . . .
O1 O 0.21563(11) 0.12740(18) 0.7705(2) 0.0245(6) Uani 1 1 d . . . . .
O2 O 0.14379(11) 0.29281(18) 0.70844(19) 0.0249(6) Uani 1 1 d . . . . .
O3 O 0.07954(11) 0.2191(2) 0.8240(2) 0.0336(7) Uani 1 1 d D . . . .
O4 O 0.0000 0.0542(3) 0.7500 0.0363(9) Uani 1 2 d DS T P . .
Cu1 Cu 0.15273(2) 0.15187(3) 0.64788(3) 0.02319(17) Uani 1 1 d . . . . .
H1O4 H 0.0270(13) 0.098(2) 0.769(3) 0.024(10) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.503(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.303(4) . ?
C2 C3 1.374(5) . ?
C3 C4 1.412(5) . ?
C3 H3 0.9300 . ?
C4 N1 1.308(4) . ?
C4 C5 1.518(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N1 1.464(4) . ?
C6 C7 1.496(8) . ?
C6 C7' 1.605(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C6 H6D 0.9700 . ?
C7 N2 1.581(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7' N2 1.513(8) . ?
C7' H7'1 0.9700 . ?
C7' H7'2 0.9700 . ?
C8 N2 1.352(7) . ?
C8 C9 1.498(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.519(13) . ?
C10 N2 1.532(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C8' C9' 1.538(13) . ?
C8' N2 1.632(9) . ?
C8' H8'1 0.9700 . ?
C8' H8'2 0.9700 . ?
C9' H9'1 0.9600 . ?
C9' H9'2 0.9600 . ?
C9' H9'3 0.9600 . ?
C10' N2 1.376(10) . ?
C10' C11' 1.522(15) . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C11' H11D 0.9600 . ?
C11' H11E 0.9600 . ?
C11' H11F 0.9600 . ?
C12 O3 1.238(4) . ?
C12 O2 1.275(4) . ?
C12 C13 1.518(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 Cu1 1.917(3) . ?
N2 Cu1 2.074(3) . ?
O1 Cu1 1.919(2) . ?
O2 Cu1 1.938(2) . ?
O4 H1O4 0.840(14) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 125.2(3) . . ?
O1 C2 C1 114.7(3) . . ?
C3 C2 C1 120.1(3) . . ?
C2 C3 C4 126.7(3) . . ?
C2 C3 H3 116.6 . . ?
C4 C3 H3 116.6 . . ?
N1 C4 C3 122.7(3) . . ?
N1 C4 C5 120.5(3) . . ?
C3 C4 C5 116.9(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C7 110.0(4) . . ?
N1 C6 C7' 106.0(4) . . ?
N1 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N1 C6 H6C 110.5 . . ?
C7' C6 H6C 110.5 . . ?
N1 C6 H6D 110.5 . . ?
C7' C6 H6D 110.5 . . ?
H6C C6 H6D 108.7 . . ?
C6 C7 N2 105.9(5) . . ?
C6 C7 H7A 110.6 . . ?
N2 C7 H7A 110.6 . . ?
C6 C7 H7B 110.6 . . ?
N2 C7 H7B 110.6 . . ?
H7A C7 H7B 108.7 . . ?
N2 C7' C6 103.9(4) . . ?
N2 C7' H7'1 111.0 . . ?
C6 C7' H7'1 111.0 . . ?
N2 C7' H7'2 111.0 . . ?
C6 C7' H7'2 111.0 . . ?
H7'1 C7' H7'2 109.0 . . ?
N2 C8 C9 113.1(7) . . ?
N2 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
N2 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N2 114.4(6) . . ?
C11 C10 H10A 108.7 . . ?
N2 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
N2 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9' C8' N2 115.5(8) . . ?
C9' C8' H8'1 108.4 . . ?
N2 C8' H8'1 108.4 . . ?
C9' C8' H8'2 108.4 . . ?
N2 C8' H8'2 108.4 . . ?
H8'1 C8' H8'2 107.5 . . ?
C8' C9' H9'1 109.5 . . ?
C8' C9' H9'2 109.5 . . ?
H9'1 C9' H9'2 109.5 . . ?
C8' C9' H9'3 109.5 . . ?
H9'1 C9' H9'3 109.5 . . ?
H9'2 C9' H9'3 109.5 . . ?
N2 C10' C11' 120.8(7) . . ?
N2 C10' H10C 107.1 . . ?
C11' C10' H10C 107.1 . . ?
N2 C10' H10D 107.1 . . ?
C11' C10' H10D 107.1 . . ?
H10C C10' H10D 106.8 . . ?
C10' C11' H11D 109.5 . . ?
C10' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C10' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
O3 C12 O2 124.4(3) . . ?
O3 C12 C13 119.9(3) . . ?
O2 C12 C13 115.7(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 N1 C6 120.4(3) . . ?
C4 N1 Cu1 126.0(2) . . ?
C6 N1 Cu1 113.5(2) . . ?
C10' N2 C7' 116.2(6) . . ?
C8 N2 C10 116.4(5) . . ?
C8 N2 C7 112.6(4) . . ?
C10 N2 C7 103.2(5) . . ?
C10' N2 C8' 108.6(5) . . ?
C7' N2 C8' 102.9(4) . . ?
C8 N2 Cu1 110.9(4) . . ?
C10' N2 Cu1 113.6(4) . . ?
C7' N2 Cu1 106.4(3) . . ?
C10 N2 Cu1 112.7(3) . . ?
C7 N2 Cu1 99.5(3) . . ?
C8' N2 Cu1 108.3(4) . . ?
C2 O1 Cu1 124.6(2) . . ?
C12 O2 Cu1 111.8(2) . . ?
N1 Cu1 O1 94.67(11) . . ?
N1 Cu1 O2 174.37(11) . . ?
O1 Cu1 O2 89.33(10) . . ?
N1 Cu1 N2 85.08(12) . . ?
O1 Cu1 N2 168.88(11) . . ?
O2 Cu1 N2 91.75(11) . . ?

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 C2 C3 C4 1.9(5) . . . . ?
C1 C2 C3 C4 -178.6(3) . . . . ?
C2 C3 C4 N1 1.6(5) . . . . ?
C2 C3 C4 C5 -178.7(3) . . . . ?
N1 C6 C7 N2 47.8(5) . . . . ?
C7' C6 C7 N2 -47.8(4) . . . . ?
N1 C6 C7' N2 -53.3(5) . . . . ?
C7 C6 C7' N2 50.0(5) . . . . ?
C3 C4 N1 C6 177.4(3) . . . . ?
C5 C4 N1 C6 -2.3(5) . . . . ?
C3 C4 N1 Cu1 -0.9(5) . . . . ?
C5 C4 N1 Cu1 179.4(2) . . . . ?
C7 C6 N1 C4 163.6(4) . . . . ?
C7' C6 N1 C4 -140.0(4) . . . . ?
C7 C6 N1 Cu1 -18.0(4) . . . . ?
C7' C6 N1 Cu1 38.4(4) . . . . ?
C9 C8 N2 C10' 94.0(9) . . . . ?
C9 C8 N2 C7' -166.9(9) . . . . ?
C9 C8 N2 C10 61.2(8) . . . . ?
C9 C8 N2 C7 -179.9(7) . . . . ?
C9 C8 N2 C8' 25.5(6) . . . . ?
C9 C8 N2 Cu1 -69.4(7) . . . . ?
C11' C10' N2 C8 17.2(13) . . . . ?
C11' C10' N2 C7' -55.7(10) . . . . ?
C11' C10' N2 C10 85.0(13) . . . . ?
C11' C10' N2 C7 -87.0(9) . . . . ?
C11' C10' N2 C8' 59.7(10) . . . . ?
C11' C10' N2 Cu1 -179.7(7) . . . . ?
C6 C7' N2 C8 148.6(6) . . . . ?
C6 C7' N2 C10' -84.1(6) . . . . ?
C6 C7' N2 C10 -113.7(7) . . . . ?
C6 C7' N2 C7 -46.3(4) . . . . ?
C6 C7' N2 C8' 157.3(5) . . . . ?
C6 C7' N2 Cu1 43.5(5) . . . . ?
C11 C10 N2 C8 52.8(9) . . . . ?
C11 C10 N2 C10' -78.8(12) . . . . ?
C11 C10 N2 C7' -21.1(12) . . . . ?
C11 C10 N2 C7 -71.0(8) . . . . ?
C11 C10 N2 C8' 76.9(8) . . . . ?
C11 C10 N2 Cu1 -177.4(6) . . . . ?
C6 C7 N2 C8 65.5(6) . . . . ?
C6 C7 N2 C10' -163.8(6) . . . . ?
C6 C7 N2 C7' 51.5(5) . . . . ?
C6 C7 N2 C10 -168.1(4) . . . . ?
C6 C7 N2 C8' 99.9(9) . . . . ?
C6 C7 N2 Cu1 -51.9(4) . . . . ?
C9' C8' N2 C8 -62.6(9) . . . . ?
C9' C8' N2 C10' 162.6(9) . . . . ?
C9' C8' N2 C7' -73.7(10) . . . . ?
C9' C8' N2 C10 149.4(10) . . . . ?
C9' C8' N2 C7 -111.8(11) . . . . ?
C9' C8' N2 Cu1 38.7(9) . . . . ?
C3 C2 O1 Cu1 -5.6(5) . . . . ?
C1 C2 O1 Cu1 174.9(2) . . . . ?
O3 C12 O2 Cu1 -1.8(4) . . . . ?
C13 C12 O2 Cu1 -179.6(2) . . . . ?

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-4

