# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mp1038
_database_code_depnum_ccdc_archive 'CCDC 1021461'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;
_audit_creation_date             2015-04-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.02.26 svn.r3159 for OlexSys, GUI svn.r3563)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 Cu N3 O4, 2.4(H2 O)'
_chemical_formula_sum            'C25 H27.80 Cu N3 O6.40'
_chemical_formula_weight         536.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.6146(17)
_cell_length_b                   12.8338(7)
_cell_length_c                   18.1002(12)
_cell_angle_alpha                90
_cell_angle_beta                 124.050(5)
_cell_angle_gamma                90
_cell_volume                     4930.0(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.000
_cell_measurement_theta_min      0.000
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  0.872849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0425 before and 0.0304 after correction.
The Ratio of minimum to maximum transmission is 0.8728.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             2232
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            39752
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        23.984
_diffrn_reflns_theta_max         23.984
_diffrn_reflns_theta_min         1.854
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3029
_reflns_number_total             3870
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         3870
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²+11.8133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1357
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H7A(0.5) H7B(0.5) O5(0.9) H5A(0.9) H5B(0.9) O6(0.8) H6A(0.8)
 H6B(0.8) O0AA(0.11) H0AA(0.11) H0AB(0.11) O1AA(0.09) H1AA(0.09) H1AB(0.09)
3.a Riding coordinates:
 O7(H7A,H7B), O0AA(H0AA,H0AB), O1AA(H1AA,H1AB)
3.b Free rotating group:
 O5(H5A,H5B), O6(H6A,H6B)
3.c Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C19(H19A,H19B), C17(H17A,H17B)
3.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C22(H22), C2(H2), C1(H1), C11(H11), C10(H10), C23(H23), C24(H24),
 C9(H9), C26(H26), C25(H25)
3.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cu Cu 0.66815(2) 0.32767(4) 0.60534(3) 0.0586(2) Uani 1 1 d . . . . .
N1 N 0.64371(15) 0.3435(2) 0.4800(2) 0.0537(8) Uani 1 1 d . . . . .
O2 O 0.71051(15) 0.3106(3) 0.7330(2) 0.0858(10) Uani 1 1 d . . . . .
N2 N 0.70436(14) 0.1953(2) 0.5960(2) 0.0507(8) Uani 1 1 d . . . . .
O4 O 0.70201(19) 0.2779(3) 0.8445(2) 0.0949(11) Uani 1 1 d . . . . .
C13 C 0.65995(16) 0.2602(3) 0.4507(2) 0.0478(9) Uani 1 1 d . . . . .
N3 N 0.58110(16) 0.3038(2) 0.6104(2) 0.0589(9) Uani 1 1 d . . . . .
C12 C 0.69331(16) 0.1793(3) 0.5148(3) 0.0472(9) Uani 1 1 d . . . . .
O1 O 0.65032(19) 0.4720(2) 0.6127(3) 0.0919(11) Uani 1 1 d . . . . .
O3 O 0.58937(18) 0.5868(2) 0.6190(2) 0.0876(10) Uani 1 1 d . . . . .
C6 C 0.66468(19) 0.1596(4) 0.3395(3) 0.0614(11) Uani 1 1 d . . . . .
C3 C 0.6107(2) 0.3332(4) 0.3061(3) 0.0743(13) Uani 1 1 d . . . . .
H3 H 0.5994 0.3311 0.2475 0.089 Uiso 1 1 calc R . . . .
C4 C 0.64559(18) 0.2507(3) 0.3647(3) 0.0563(10) Uani 1 1 d . . . . .
C8 C 0.71086(18) 0.0893(3) 0.4900(3) 0.0573(10) Uani 1 1 d . . . . .
C14 C 0.6480(2) 0.1521(5) 0.2456(3) 0.0912(17) Uani 1 1 d . . . . .
H14A H 0.6054 0.1280 0.2068 0.137 Uiso 1 1 calc GR . . . .
H14B H 0.6760 0.1039 0.2439 0.137 Uiso 1 1 calc GR . . . .
H14C H 0.6521 0.2195 0.2262 0.137 Uiso 1 1 calc GR . . . .
C22 C 0.5688(2) 0.0588(4) 0.5461(4) 0.0813(14) Uani 1 1 d . . . . .
H22 H 0.5774 0.0489 0.6028 0.098 Uiso 1 1 calc R . . . .
C2 C 0.5933(2) 0.4166(4) 0.3348(3) 0.0823(14) Uani 1 1 d . . . . .
H2 H 0.5697 0.4706 0.2958 0.099 Uiso 1 1 calc R . . . .
C16 C 0.6032(2) 0.4964(3) 0.6139(3) 0.0625(11) Uani 1 1 d . . . . .
C1 C 0.6110(2) 0.4201(3) 0.4225(3) 0.0731(12) Uani 1 1 d . . . . .
H1 H 0.5998 0.4777 0.4418 0.088 Uiso 1 1 calc R . . . .
C7 C 0.6954(2) 0.0800(3) 0.4002(3) 0.0660(12) Uani 1 1 d . . . . .
C11 C 0.7346(2) 0.1211(4) 0.6576(3) 0.0686(12) Uani 1 1 d . . . . .
H11 H 0.7434 0.1315 0.7143 0.082 Uiso 1 1 calc R . . . .
C10 C 0.7532(2) 0.0292(4) 0.6389(4) 0.0820(14) Uani 1 1 d . . . . .
H10 H 0.7738 -0.0216 0.6828 0.098 Uiso 1 1 calc R . . . .
C20 C 0.5263(2) 0.2389(4) 0.5427(4) 0.0853(15) Uani 1 1 d . . . . .
H20A H 0.4958 0.2837 0.4944 0.102 Uiso 1 1 calc R . . . .
H20B H 0.5063 0.2094 0.5702 0.102 Uiso 1 1 calc R . . . .
C18 C 0.6792(2) 0.2866(3) 0.7643(3) 0.0641(11) Uani 1 1 d . . . . .
C19 C 0.6108(3) 0.2588(5) 0.6981(3) 0.0928(16) Uani 1 1 d . . . . .
H19A H 0.6075 0.1836 0.6919 0.111 Uiso 1 1 calc R . . . .
H19B H 0.5872 0.2801 0.7228 0.111 Uiso 1 1 calc R . . . .
C23 C 0.5821(3) -0.0194(5) 0.5095(6) 0.116(2) Uani 1 1 d . . . . .
H23 H 0.6000 -0.0809 0.5409 0.139 Uiso 1 1 calc R . . . .
C15 C 0.7139(3) -0.0200(4) 0.3762(4) 0.0999(18) Uani 1 1 d . . . . .
H15A H 0.6856 -0.0747 0.3683 0.150 Uiso 1 1 calc GR . . . .
H15B H 0.7562 -0.0384 0.4232 0.150 Uiso 1 1 calc GR . . . .
H15C H 0.7115 -0.0102 0.3218 0.150 Uiso 1 1 calc GR . . . .
C24 C 0.5696(4) -0.0077(8) 0.4306(7) 0.138(3) Uani 1 1 d . . . . .
H24 H 0.5795 -0.0628 0.4072 0.166 Uiso 1 1 calc R . . . .
C21 C 0.54327(18) 0.1521(3) 0.5044(3) 0.0641(11) Uani 1 1 d . . . . .
C9 C 0.7415(2) 0.0129(3) 0.5568(4) 0.0750(13) Uani 1 1 d . . . . .
H9 H 0.7539 -0.0493 0.5446 0.090 Uiso 1 1 calc R . . . .
C26 C 0.5295(3) 0.1633(6) 0.4191(4) 0.113(2) Uani 1 1 d . . . . .
H26 H 0.5115 0.2244 0.3871 0.135 Uiso 1 1 calc R . . . .
C25 C 0.5441(4) 0.0760(9) 0.3799(5) 0.130(3) Uani 1 1 d . . . . .
H25 H 0.5358 0.0798 0.3229 0.156 Uiso 1 1 calc R . . . .
C17 C 0.5602(2) 0.4109(4) 0.6063(4) 0.0891(16) Uani 1 1 d . . . . .
H17A H 0.5536 0.4202 0.6537 0.107 Uiso 1 1 calc R . . . .
H17B H 0.5196 0.4198 0.5502 0.107 Uiso 1 1 calc R . . . .
O7 O 1.0000 0.1285(5) 1.2500 0.1192(19) Uani 1 2 d S T P . .
H7A H 0.9645 0.1548 1.2108 0.179 Uiso 0.5 1 d R . . . .
H7B H 1.0208 0.1715 1.2926 0.179 Uiso 0.5 1 d R . . . .
O5 O 0.8453(2) 0.2308(4) 0.9342(3) 0.1031(13) Uani 0.9 1 d . . . A 1
H5A H 0.8574 0.1859 0.9124 0.155 Uiso 0.9 1 d G . . A 1
H5B H 0.8055 0.2379 0.8999 0.155 Uiso 0.9 1 d G . . A 1
O6 O 0.8921(3) 0.2251(7) 1.1133(3) 0.140(2) Uani 0.8 1 d . . . B 1
H6A H 0.8834 0.2237 1.0606 0.211 Uiso 0.8 1 d G . . B 1
H6B H 0.8582 0.2260 1.1113 0.211 Uiso 0.8 1 d G . . B 1
O0AA O 0.8009(16) 0.243(3) 1.007(2) 0.106(11) Uiso 0.11 1 d . . . C 2
H0AA H 0.7974 0.3075 0.9937 0.159 Uiso 0.11 1 d R . . C 2
H0AB H 0.8271 0.2363 1.0633 0.159 Uiso 0.11 1 d R . . C 2
O1AA O 0.913(2) 0.176(4) 1.048(3) 0.113(15) Uiso 0.09 1 d . . . D 2
H1AA H 0.9282 0.2340 1.0464 0.169 Uiso 0.09 1 d R . . D 2
H1AB H 0.9117 0.1347 1.0100 0.169 Uiso 0.09 1 d R . . D 2


_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
Cu N1 1.996(3) . ?
Cu O2 1.938(3) . ?
Cu N2 1.988(3) . ?
Cu N3 2.302(3) . ?
Cu O1 1.929(3) . ?
N1 C13 1.359(5) . ?
N1 C1 1.333(5) . ?
O2 C18 1.254(5) . ?
N2 C12 1.348(5) . ?
N2 C11 1.334(5) . ?
O4 C18 1.229(5) . ?
C13 C12 1.429(5) . ?
C13 C4 1.390(5) . ?
N3 C20 1.497(6) . ?
N3 C19 1.443(6) . ?
N3 C17 1.462(5) . ?
C12 C8 1.402(5) . ?
O1 C16 1.260(5) . ?
O3 C16 1.231(5) . ?
C6 C4 1.436(6) . ?
C6 C14 1.506(6) . ?
C6 C7 1.380(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.409(6) . ?
C3 C2 1.370(7) . ?
C8 C7 1.446(6) . ?
C8 C9 1.406(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C22 H22 0.9300 . ?
C22 C23 1.346(8) . ?
C22 C21 1.370(6) . ?
C2 H2 0.9300 . ?
C2 C1 1.385(7) . ?
C16 C17 1.505(7) . ?
C1 H1 0.9300 . ?
C7 C15 1.512(6) . ?
C11 H11 0.9300 . ?
C11 C10 1.383(7) . ?
C10 H10 0.9300 . ?
C10 C9 1.358(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.499(6) . ?
C18 C19 1.510(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C23 H23 0.9300 . ?
C23 C24 1.286(10) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C24 H24 0.9300 . ?
C24 C25 1.324(11) . ?
C21 C26 1.385(7) . ?
C9 H9 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.482(11) . ?
C25 H25 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
O7 H7A 0.8499 . ?
O7 H7B 0.8501 . ?
O5 H5A 0.8504 . ?
O5 H5B 0.8501 . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8500 . ?
O0AA H0AA 0.8493 . ?
O0AA H0AB 0.8497 . ?
O1AA H1AA 0.8499 . ?
O1AA H1AB 0.8503 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu N3 111.32(13) . . ?
O2 Cu N1 167.37(13) . . ?
O2 Cu N2 91.63(14) . . ?
O2 Cu N3 81.15(13) . . ?
N2 Cu N1 81.65(12) . . ?
N2 Cu N3 113.46(12) . . ?
O1 Cu N1 92.56(14) . . ?
O1 Cu O2 91.29(16) . . ?
O1 Cu N2 164.98(14) . . ?
O1 Cu N3 81.55(13) . . ?
C13 N1 Cu 113.2(2) . . ?
C1 N1 Cu 128.5(3) . . ?
C1 N1 C13 118.1(4) . . ?
C18 O2 Cu 119.6(3) . . ?
C12 N2 Cu 113.5(2) . . ?
C11 N2 Cu 128.3(3) . . ?
C11 N2 C12 118.1(3) . . ?
N1 C13 C12 115.4(3) . . ?
N1 C13 C4 124.0(4) . . ?
C4 C13 C12 120.6(3) . . ?
C20 N3 Cu 121.8(3) . . ?
C19 N3 Cu 99.9(3) . . ?
C19 N3 C20 110.7(4) . . ?
C19 N3 C17 112.6(4) . . ?
C17 N3 Cu 102.1(3) . . ?
C17 N3 C20 109.4(4) . . ?
N2 C12 C13 116.1(3) . . ?
N2 C12 C8 124.4(4) . . ?
C8 C12 C13 119.4(4) . . ?
C16 O1 Cu 120.4(3) . . ?
C4 C6 C14 118.6(4) . . ?
C7 C6 C4 119.6(4) . . ?
C7 C6 C14 121.7(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(4) . . ?
C13 C4 C6 120.2(4) . . ?
C13 C4 C3 115.8(4) . . ?
C3 C4 C6 123.9(4) . . ?
C12 C8 C7 119.5(4) . . ?
C12 C8 C9 115.1(4) . . ?
C9 C8 C7 125.3(4) . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C23 C22 H22 118.2 . . ?
C23 C22 C21 123.7(6) . . ?
C21 C22 H22 118.2 . . ?
C3 C2 H2 120.2 . . ?
C3 C2 C1 119.5(4) . . ?
C1 C2 H2 120.2 . . ?
O1 C16 C17 118.5(4) . . ?
O3 C16 O1 123.7(4) . . ?
O3 C16 C17 117.8(4) . . ?
N1 C1 C2 122.1(4) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 C15 122.0(4) . . ?
C8 C7 C15 117.4(5) . . ?
N2 C11 H11 119.2 . . ?
N2 C11 C10 121.6(4) . . ?
C10 C11 H11 119.2 . . ?
C11 C10 H10 119.9 . . ?
C9 C10 C11 120.2(4) . . ?
C9 C10 H10 119.9 . . ?
N3 C20 H20A 108.7 . . ?
N3 C20 H20B 108.7 . . ?
N3 C20 C21 114.2(4) . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
O2 C18 C19 116.8(4) . . ?
O4 C18 O2 123.7(5) . . ?
O4 C18 C19 119.3(5) . . ?
N3 C19 C18 116.2(4) . . ?
N3 C19 H19A 108.2 . . ?
N3 C19 H19B 108.2 . . ?
C18 C19 H19A 108.2 . . ?
C18 C19 H19B 108.2 . . ?
H19A C19 H19B 107.4 . . ?
C22 C23 H23 120.5 . . ?
C24 C23 C22 119.0(8) . . ?
C24 C23 H23 120.5 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C23 C24 H24 117.1 . . ?
C23 C24 C25 125.8(9) . . ?
C25 C24 H24 117.1 . . ?
C22 C21 C20 124.6(5) . . ?
C22 C21 C26 116.7(5) . . ?
C26 C21 C20 118.6(5) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C21 C26 H26 120.6 . . ?
C21 C26 C25 118.8(6) . . ?
C25 C26 H26 120.6 . . ?
C24 C25 C26 116.1(7) . . ?
C24 C25 H25 122.0 . . ?
C26 C25 H25 122.0 . . ?
N3 C17 C16 116.8(4) . . ?
N3 C17 H17A 108.1 . . ?
N3 C17 H17B 108.1 . . ?
C16 C17 H17A 108.1 . . ?
C16 C17 H17B 108.1 . . ?
H17A C17 H17B 107.3 . . ?
H7A O7 H7B 109.5 . . ?
H5A O5 H5B 109.5 . . ?
H6A O6 H6B 109.5 . . ?
H0AA O0AA H0AB 109.5 . . ?
H1AA O1AA H1AB 109.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A O6 0.85 1.92 2.764(7) 169.7 .
O7 H7B O6 0.85 2.02 2.764(7) 145.1 2_757
O6 H6A O5 0.85 1.92 2.756(6) 167.0 .
O0AA H0AB O4 0.85 2.18 2.74(4) 122.7 7_657

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
Cu N1 C13 C12 -2.4(4) . . . . ?
Cu N1 C13 C4 177.1(3) . . . . ?
Cu N1 C1 C2 -174.8(3) . . . . ?
Cu O2 C18 O4 -177.4(3) . . . . ?
Cu O2 C18 C19 7.7(6) . . . . ?
Cu N2 C12 C13 2.1(4) . . . . ?
Cu N2 C12 C8 -176.3(3) . . . . ?
Cu N2 C11 C10 175.2(3) . . . . ?
Cu N3 C20 C21 29.7(6) . . . . ?
Cu N3 C19 C18 26.1(5) . . . . ?
Cu N3 C17 C16 -8.5(5) . . . . ?
Cu O1 C16 O3 179.5(3) . . . . ?
Cu O1 C16 C17 -2.1(6) . . . . ?
N1 C13 C12 N2 0.2(5) . . . . ?
N1 C13 C12 C8 178.7(3) . . . . ?
N1 C13 C4 C6 -180.0(3) . . . . ?
N1 C13 C4 C3 -1.6(5) . . . . ?
O2 C18 C19 N3 -26.1(7) . . . . ?
N2 C12 C8 C7 178.8(3) . . . . ?
N2 C12 C8 C9 0.4(5) . . . . ?
N2 C11 C10 C9 0.8(7) . . . . ?
O4 C18 C19 N3 158.8(4) . . . . ?
C13 N1 C1 C2 0.3(6) . . . . ?
C13 C12 C8 C7 0.5(5) . . . . ?
C13 C12 C8 C9 -177.9(3) . . . . ?
N3 C20 C21 C22 79.5(6) . . . . ?
N3 C20 C21 C26 -104.1(5) . . . . ?
C12 N2 C11 C10 -1.4(6) . . . . ?
C12 C13 C4 C6 -0.5(5) . . . . ?
C12 C13 C4 C3 177.9(3) . . . . ?
C12 C8 C7 C6 1.2(6) . . . . ?
C12 C8 C7 C15 -178.4(4) . . . . ?
C12 C8 C9 C10 -1.0(6) . . . . ?
O1 C16 C17 N3 8.2(7) . . . . ?
O3 C16 C17 N3 -173.3(4) . . . . ?
C3 C2 C1 N1 -1.3(7) . . . . ?
C4 C13 C12 N2 -179.3(3) . . . . ?
C4 C13 C12 C8 -0.8(5) . . . . ?
C4 C6 C7 C8 -2.5(6) . . . . ?
C4 C6 C7 C15 177.0(4) . . . . ?
C4 C3 C2 C1 0.9(7) . . . . ?
C14 C6 C4 C13 179.8(4) . . . . ?
C14 C6 C4 C3 1.5(6) . . . . ?
C14 C6 C7 C8 180.0(4) . . . . ?
C14 C6 C7 C15 -0.5(6) . . . . ?
C22 C23 C24 C25 -0.2(11) . . . . ?
C22 C21 C26 C25 -1.1(7) . . . . ?
C2 C3 C4 C13 0.5(6) . . . . ?
C2 C3 C4 C6 178.8(4) . . . . ?
C1 N1 C13 C12 -178.2(4) . . . . ?
C1 N1 C13 C4 1.3(5) . . . . ?
C7 C6 C4 C13 2.2(6) . . . . ?
C7 C6 C4 C3 -176.0(4) . . . . ?
C7 C8 C9 C10 -179.3(4) . . . . ?
C11 N2 C12 C13 179.1(3) . . . . ?
C11 N2 C12 C8 0.8(5) . . . . ?
C11 C10 C9 C8 0.5(7) . . . . ?
C20 N3 C19 C18 155.6(4) . . . . ?
C20 N3 C17 C16 -138.8(5) . . . . ?
C20 C21 C26 C25 -177.8(4) . . . . ?
C19 N3 C20 C21 -87.0(5) . . . . ?
C19 N3 C17 C16 97.7(5) . . . . ?
C23 C22 C21 C20 178.1(5) . . . . ?
C23 C22 C21 C26 1.6(7) . . . . ?
C23 C24 C25 C26 0.6(11) . . . . ?
C21 C22 C23 C24 -1.0(9) . . . . ?
C21 C26 C25 C24 0.1(9) . . . . ?
C9 C8 C7 C6 179.4(4) . . . . ?
C9 C8 C7 C15 -0.1(6) . . . . ?
C17 N3 C20 C21 148.3(4) . . . . ?
C17 N3 C19 C18 -81.5(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mprl4
_database_code_depnum_ccdc_archive 'CCDC 1021462'
_audit_update_record             
;
2015-03-04 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 Cu N3 O6'
_chemical_formula_weight         500.98

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.873(3)
_cell_length_b                   16.336(5)
_cell_length_c                   13.048(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.869(4)
_cell_angle_gamma                90.00
_cell_volume                     2073.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1036
_exptl_absorpt_coefficient_mu    1.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6198
_exptl_absorpt_correction_T_max  0.7193
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'APEX II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31684
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         27.50
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0
_reflns_number_total             4729
_reflns_number_gt                4121
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX-II (BRUKER-NONIUS, 2003)'
_computing_cell_refinement       
; 
  APEX-II(BRUKER-NONIUS, 2003) 
;
_computing_data_reduction        APEX-II
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    Olex2
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0620P)²+4.8966P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4729
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.86743(3) 0.73871(2) 0.44059(3) 0.01582(13) Uani 1 1 d . . .
O1 O 1.0058(2) 0.82316(13) 0.45873(17) 0.0228(5) Uani 1 1 d . . .
O2 O 1.1704(2) 0.88622(14) 0.56672(19) 0.0278(5) Uani 1 1 d . . .
O3 O 0.9962(2) 0.65890(13) 0.39858(16) 0.0216(5) Uani 1 1 d . . .
O4 O 1.1495(2) 0.56094(14) 0.44822(18) 0.0272(5) Uani 1 1 d . . .
N1 N 0.7077(2) 0.66200(15) 0.41277(18) 0.0167(5) Uani 1 1 d . . .
N2 N 0.7178(2) 0.82288(15) 0.41665(18) 0.0152(5) Uani 1 1 d . . .
N3 N 0.9792(3) 0.69937(15) 0.60300(19) 0.0189(5) Uani 1 1 d . . .
C1 C 0.7072(3) 0.58111(19) 0.4106(3) 0.0228(6) Uani 1 1 d . . .
H1 H 0.7926 0.5528 0.4212 0.027 Uiso 1 1 calc R . .
C2 C 0.5851(3) 0.5357(2) 0.3933(3) 0.0280(7) Uani 1 1 d . . .
H2 H 0.5884 0.4776 0.3920 0.034 Uiso 1 1 calc R . .
C3 C 0.4606(3) 0.57526(19) 0.3781(3) 0.0241(6) Uani 1 1 d . . .
H3 H 0.3773 0.5449 0.3665 0.029 Uiso 1 1 calc R . .
C4 C 0.4581(3) 0.66146(18) 0.3800(2) 0.0176(6) Uani 1 1 d . . .
C5 C 0.5852(3) 0.70168(17) 0.3972(2) 0.0152(5) Uani 1 1 d . . .
C6 C 0.3344(3) 0.70918(19) 0.3647(2) 0.0196(6) Uani 1 1 d . . .
H6 H 0.2478 0.6823 0.3536 0.024 Uiso 1 1 calc R . .
C7 C 0.3395(3) 0.79274(19) 0.3658(2) 0.0200(6) Uani 1 1 d . . .
H7 H 0.2565 0.8233 0.3554 0.024 Uiso 1 1 calc R . .
C8 C 0.4690(3) 0.83478(18) 0.3824(2) 0.0175(6) Uani 1 1 d . . .
C10 C 0.5906(3) 0.78882(18) 0.3986(2) 0.0152(5) Uani 1 1 d . . .
C11 C 0.4822(3) 0.92043(19) 0.3829(2) 0.0223(6) Uani 1 1 d . . .
H11 H 0.4029 0.9544 0.3716 0.027 Uiso 1 1 calc R . .
C12 C 0.6116(3) 0.95451(19) 0.4001(3) 0.0247(7) Uani 1 1 d . . .
H12 H 0.6221 1.0123 0.4002 0.030 Uiso 1 1 calc R . .
C13 C 0.7281(3) 0.90378(18) 0.4174(2) 0.0208(6) Uani 1 1 d . . .
H13 H 0.8168 0.9281 0.4300 0.025 Uiso 1 1 calc R . .
C14 C 1.0857(3) 0.83012(18) 0.5452(2) 0.0202(6) Uani 1 1 d . . .
C15 C 1.0769(4) 0.7674(2) 0.6304(3) 0.0275(7) Uani 1 1 d . . .
H15A H 1.1696 0.7439 0.6528 0.033 Uiso 1 1 calc R . .
H15B H 1.0516 0.7966 0.6909 0.033 Uiso 1 1 calc R . .
C16 C 1.0688(3) 0.61458(18) 0.4672(2) 0.0194(6) Uani 1 1 d . . .
C17 C 1.0492(3) 0.62382(19) 0.5796(2) 0.0237(6) Uani 1 1 d . . .
H17A H 0.9957 0.5764 0.5979 0.028 Uiso 1 1 calc R . .
H17B H 1.1406 0.6218 0.6247 0.028 Uiso 1 1 calc R . .
C18 C 0.8975(3) 0.6840(2) 0.6878(2) 0.0252(7) Uani 1 1 d . . .
H18A H 0.9511 0.7029 0.7547 0.030 Uiso 1 1 calc R . .
H18B H 0.8826 0.6244 0.6934 0.030 Uiso 1 1 calc R . .
C19 C 0.7600(3) 0.72673(19) 0.6695(2) 0.0199(6) Uani 1 1 d . . .
C20 C 0.6400(4) 0.6793(2) 0.6528(2) 0.0261(7) Uani 1 1 d . . .
H20 H 0.6469 0.6213 0.6529 0.031 Uiso 1 1 calc R . .
C21 C 0.5114(4) 0.7159(2) 0.6361(3) 0.0296(7) Uani 1 1 d . . .
H21 H 0.4310 0.6829 0.6251 0.036 Uiso 1 1 calc R . .
C22 C 0.4997(4) 0.7996(2) 0.6353(2) 0.0301(7) Uani 1 1 d . . .
H22 H 0.4116 0.8247 0.6234 0.036 Uiso 1 1 calc R . .
C23 C 0.6179(4) 0.8473(2) 0.6521(2) 0.0278(7) Uani 1 1 d . . .
H23 H 0.6101 0.9052 0.6517 0.033 Uiso 1 1 calc R . .
C24 C 0.7469(3) 0.8114(2) 0.6695(2) 0.0245(6) Uani 1 1 d . . .
H24 H 0.8268 0.8449 0.6815 0.029 Uiso 1 1 calc R . .
O5 O 0.8420(3) 0.47848(18) 0.1348(2) 0.0440(7) Uani 1 1 d . . .
H5A H 0.8381 0.4523 0.0780 0.066 Uiso 1 1 d R . .
H5B H 0.9255 0.4877 0.1608 0.066 Uiso 1 1 d R . .
O6 O 1.1171(3) 0.51689(15) 0.23766(19) 0.0331(6) Uani 1 1 d . . .
H6A H 1.1479 0.5548 0.1945 0.050 Uiso 1 1 d R . .
H6B H 1.1255 0.5372 0.3022 0.050 Uiso 1 1 d R . .


_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(2) . ?
Cu1 O3 1.964(2) . ?
Cu1 N1 1.998(2) . ?
Cu1 N2 2.003(2) . ?
Cu1 N3 2.306(3) . ?
O1 C14 1.266(4) . ?
O2 C14 1.240(4) . ?
O3 C16 1.272(4) . ?
O4 C16 1.238(4) . ?
N1 C1 1.322(4) . ?
N1 C5 1.356(4) . ?
N2 C13 1.325(4) . ?
N2 C10 1.357(4) . ?
N3 C17 1.472(4) . ?
N3 C15 1.475(4) . ?
N3 C18 1.497(4) . ?
C1 C2 1.401(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.372(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(4) . ?
C4 C6 1.433(4) . ?
C5 C10 1.425(4) . ?
C6 C7 1.366(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.434(4) . ?
C7 H7 0.9500 . ?
C8 C10 1.401(4) . ?
C8 C11 1.405(4) . ?
C11 C12 1.376(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.525(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.519(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.509(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C24 1.390(4) . ?
C19 C20 1.401(5) . ?
C20 C21 1.387(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.372(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
O5 H5A 0.8501 . ?
O5 H5B 0.8500 . ?
O6 H6A 0.9226 . ?
O6 H6B 0.8951 . ?

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 O3 91.73(10) . . ?
O1 Cu1 N1 172.72(9) . . ?
O3 Cu1 N1 93.52(10) . . ?
O1 Cu1 N2 90.93(10) . . ?
O3 Cu1 N2 155.20(9) . . ?
N1 Cu1 N2 82.20(10) . . ?
O1 Cu1 N3 82.48(9) . . ?
O3 Cu1 N3 80.84(9) . . ?
N1 Cu1 N3 103.33(9) . . ?
N2 Cu1 N3 123.95(9) . . ?
C14 O1 Cu1 119.60(19) . . ?
C16 O3 Cu1 119.66(19) . . ?
C1 N1 C5 118.3(3) . . ?
C1 N1 Cu1 129.1(2) . . ?
C5 N1 Cu1 112.53(19) . . ?
C13 N2 C10 118.6(3) . . ?
C13 N2 Cu1 129.0(2) . . ?
C10 N2 Cu1 112.43(19) . . ?
C17 N3 C15 111.8(3) . . ?
C17 N3 C18 110.1(2) . . ?
C15 N3 C18 111.1(3) . . ?
C17 N3 Cu1 102.16(17) . . ?
C15 N3 Cu1 101.67(18) . . ?
C18 N3 Cu1 119.46(19) . . ?
N1 C1 C2 122.2(3) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 116.9(3) . . ?
C5 C4 C6 119.1(3) . . ?
C3 C4 C6 124.0(3) . . ?
N1 C5 C4 123.5(3) . . ?
N1 C5 C10 116.5(2) . . ?
C4 C5 C10 120.1(3) . . ?
C7 C6 C4 120.9(3) . . ?
C7 C6 H6 119.6 . . ?
C4 C6 H6 119.6 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C10 C8 C11 117.2(3) . . ?
C10 C8 C7 119.0(3) . . ?
C11 C8 C7 123.9(3) . . ?
N2 C10 C8 123.4(3) . . ?
N2 C10 C5 116.3(2) . . ?
C8 C10 C5 120.3(3) . . ?
C12 C11 C8 119.1(3) . . ?
C12 C11 H11 120.4 . . ?
C8 C11 H11 120.4 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
N2 C13 C12 121.8(3) . . ?
N2 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
O2 C14 O1 124.1(3) . . ?
O2 C14 C15 116.8(3) . . ?
O1 C14 C15 119.0(3) . . ?
N3 C15 C14 116.5(3) . . ?
N3 C15 H15A 108.2 . . ?
C14 C15 H15A 108.2 . . ?
N3 C15 H15B 108.2 . . ?
C14 C15 H15B 108.2 . . ?
H15A C15 H15B 107.3 . . ?
O4 C16 O3 124.5(3) . . ?
O4 C16 C17 117.1(3) . . ?
O3 C16 C17 118.3(3) . . ?
N3 C17 C16 115.2(2) . . ?
N3 C17 H17A 108.5 . . ?
C16 C17 H17A 108.5 . . ?
N3 C17 H17B 108.5 . . ?
C16 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
N3 C18 C19 113.0(2) . . ?
N3 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
N3 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C24 C19 C20 118.4(3) . . ?
C24 C19 C18 122.8(3) . . ?
C20 C19 C18 118.9(3) . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 120.3(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.3(3) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C19 120.2(3) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
H5A O5 H5B 109.5 . . ?
H6A O6 H6B 109.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Cu1 O1 C14 -87.3(2) . . . . ?
N1 Cu1 O1 C14 136.5(7) . . . . ?
N2 Cu1 O1 C14 117.4(2) . . . . ?
N3 Cu1 O1 C14 -6.8(2) . . . . ?
O1 Cu1 O3 C16 90.3(2) . . . . ?
N1 Cu1 O3 C16 -94.8(2) . . . . ?
N2 Cu1 O3 C16 -173.7(2) . . . . ?
N3 Cu1 O3 C16 8.2(2) . . . . ?
O1 Cu1 N1 C1 159.9(7) . . . . ?
O3 Cu1 N1 C1 23.9(3) . . . . ?
N2 Cu1 N1 C1 179.3(3) . . . . ?
N3 Cu1 N1 C1 -57.6(3) . . . . ?
O1 Cu1 N1 C5 -22.0(9) . . . . ?
O3 Cu1 N1 C5 -158.09(19) . . . . ?
N2 Cu1 N1 C5 -2.65(19) . . . . ?
N3 Cu1 N1 C5 120.50(19) . . . . ?
O1 Cu1 N2 C13 -0.9(3) . . . . ?
O3 Cu1 N2 C13 -97.0(3) . . . . ?
N1 Cu1 N2 C13 -178.5(3) . . . . ?
N3 Cu1 N2 C13 80.7(3) . . . . ?
O1 Cu1 N2 C10 179.83(19) . . . . ?
O3 Cu1 N2 C10 83.7(3) . . . . ?
N1 Cu1 N2 C10 2.24(19) . . . . ?
N3 Cu1 N2 C10 -98.62(19) . . . . ?
O1 Cu1 N3 C17 -108.35(19) . . . . ?
O3 Cu1 N3 C17 -15.36(19) . . . . ?
N1 Cu1 N3 C17 76.1(2) . . . . ?
N2 Cu1 N3 C17 165.62(18) . . . . ?
O1 Cu1 N3 C15 7.3(2) . . . . ?
O3 Cu1 N3 C15 100.3(2) . . . . ?
N1 Cu1 N3 C15 -168.3(2) . . . . ?
N2 Cu1 N3 C15 -78.8(2) . . . . ?
O1 Cu1 N3 C18 129.9(2) . . . . ?
O3 Cu1 N3 C18 -137.1(2) . . . . ?
N1 Cu1 N3 C18 -45.6(2) . . . . ?
N2 Cu1 N3 C18 43.9(3) . . . . ?
C5 N1 C1 C2 -0.2(5) . . . . ?
Cu1 N1 C1 C2 177.7(2) . . . . ?
N1 C1 C2 C3 -0.2(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C2 C3 C4 C6 179.7(3) . . . . ?
C1 N1 C5 C4 0.6(4) . . . . ?
Cu1 N1 C5 C4 -177.7(2) . . . . ?
C1 N1 C5 C10 -179.1(3) . . . . ?
Cu1 N1 C5 C10 2.6(3) . . . . ?
C3 C4 C5 N1 -0.6(4) . . . . ?
C6 C4 C5 N1 179.8(3) . . . . ?
C3 C4 C5 C10 179.1(3) . . . . ?
C6 C4 C5 C10 -0.5(4) . . . . ?
C5 C4 C6 C7 0.6(4) . . . . ?
C3 C4 C6 C7 -178.9(3) . . . . ?
C4 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C10 -0.7(4) . . . . ?
C6 C7 C8 C11 179.0(3) . . . . ?
C13 N2 C10 C8 -1.1(4) . . . . ?
Cu1 N2 C10 C8 178.2(2) . . . . ?
C13 N2 C10 C5 179.2(2) . . . . ?
Cu1 N2 C10 C5 -1.5(3) . . . . ?
C11 C8 C10 N2 1.5(4) . . . . ?
C7 C8 C10 N2 -178.9(3) . . . . ?
C11 C8 C10 C5 -178.8(3) . . . . ?
C7 C8 C10 C5 0.8(4) . . . . ?
N1 C5 C10 N2 -0.8(4) . . . . ?
C4 C5 C10 N2 179.5(2) . . . . ?
N1 C5 C10 C8 179.5(2) . . . . ?
C4 C5 C10 C8 -0.2(4) . . . . ?
C10 C8 C11 C12 -0.6(4) . . . . ?
C7 C8 C11 C12 179.8(3) . . . . ?
C8 C11 C12 C13 -0.4(5) . . . . ?
C10 N2 C13 C12 0.0(4) . . . . ?
Cu1 N2 C13 C12 -179.3(2) . . . . ?
C11 C12 C13 N2 0.8(5) . . . . ?
Cu1 O1 C14 O2 -174.2(2) . . . . ?
Cu1 O1 C14 C15 4.4(4) . . . . ?
C17 N3 C15 C14 101.0(3) . . . . ?
C18 N3 C15 C14 -135.5(3) . . . . ?
Cu1 N3 C15 C14 -7.3(3) . . . . ?
O2 C14 C15 N3 -178.0(3) . . . . ?
O1 C14 C15 N3 3.3(4) . . . . ?
Cu1 O3 C16 O4 177.7(2) . . . . ?
Cu1 O3 C16 C17 1.7(4) . . . . ?
C15 N3 C17 C16 -87.6(3) . . . . ?
C18 N3 C17 C16 148.4(3) . . . . ?
Cu1 N3 C17 C16 20.4(3) . . . . ?
O4 C16 C17 N3 166.3(3) . . . . ?
O3 C16 C17 N3 -17.5(4) . . . . ?
C17 N3 C18 C19 -140.0(3) . . . . ?
C15 N3 C18 C19 95.5(3) . . . . ?
Cu1 N3 C18 C19 -22.3(3) . . . . ?
N3 C18 C19 C24 -65.9(4) . . . . ?
N3 C18 C19 C20 114.7(3) . . . . ?
C24 C19 C20 C21 0.3(4) . . . . ?
C18 C19 C20 C21 179.8(3) . . . . ?
C19 C20 C21 C22 0.3(5) . . . . ?
C20 C21 C22 C23 -0.5(5) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C22 C23 C24 C19 0.5(5) . . . . ?
C20 C19 C24 C23 -0.7(4) . . . . ?
C18 C19 C24 C23 179.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.752
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.111
