# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_shelx
_audit_block_doi                 10.5517/cc1j5cjl
_database_code_depnum_ccdc_archive 'CCDC 1405339'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 Cu N4 O7'
_chemical_formula_weight         505.96

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.74690(10)
_cell_length_b                   20.6365(2)
_cell_length_c                   9.28010(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.2040(10)
_cell_angle_gamma                90
_cell_volume                     1089.32(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8487
_cell_measurement_theta_min      4.8160
_cell_measurement_theta_max      70.4980

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             522
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.111
_exptl_absorpt_coefficient_mu    1.871
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.72637
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_reflns_number            9949
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.285
_diffrn_reflns_theta_max         70.684
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 0.911
_reflns_number_total             3772
_reflns_number_gt                3741
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.806
_reflns_Friedel_fraction_full    0.817

_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       
'CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.37.35'
_computing_cell_refinement       
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.37.35'
_computing_data_reduction        
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.37.35'

_computing_structure_solution    'SIR-97_(Altomare & al., 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.3(CCDC, 2014)'
_computing_publication_material  'WINGX (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.3243P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1597 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3772
_refine_ls_number_parameters     299
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.79410(6) 0.87639(2) 0.09700(4) 0.01679(14) Uani 1 1 d . . . . .
O2 O 1.0578(4) 0.86718(13) -0.0108(2) 0.0232(5) Uani 1 1 d . . . . .
O3 O 1.2355(4) 0.91168(14) -0.1829(2) 0.0263(5) Uani 1 1 d . . . . .
O4 O 1.1414(7) 1.0726(2) 0.1410(4) 0.0643(12) Uani 1 1 d . . . . .
O5 O 0.9403(7) 1.15400(16) 0.1893(4) 0.0520(8) Uani 1 1 d . . . . .
O6 O 0.7759(9) 1.0614(2) 0.1627(4) 0.0768(15) Uani 1 1 d . . . . .
N1 N 0.5888(5) 0.89978(13) 0.2500(3) 0.0182(5) Uani 1 1 d . . . . .
N2 N 0.9360(5) 0.81465(14) 0.2517(3) 0.0196(5) Uani 1 1 d . . . . .
N3 N 0.7032(4) 0.95025(14) -0.0377(3) 0.0171(5) Uani 1 1 d . . . . .
H3A H 0.5492 0.9464 -0.0766 0.021 Uiso 1 1 calc R U . . .
H3B H 0.7210 0.9882 0.0127 0.021 Uiso 1 1 calc R U . . .
N4 N 0.9510(6) 1.09578(17) 0.1639(3) 0.0335(7) Uani 1 1 d . . . . .
C1 C 0.4111(6) 0.94116(17) 0.2441(3) 0.0214(6) Uani 1 1 d . . . . .
H1 H 0.3741 0.9673 0.1597 0.026 Uiso 1 1 calc R U . . .
C2 C 0.2759(6) 0.94777(18) 0.3577(4) 0.0244(7) Uani 1 1 d . . . . .
H2 H 0.1485 0.9775 0.3490 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3285(6) 0.91107(18) 0.4814(4) 0.0253(7) Uani 1 1 d . . . . .
H3 H 0.2387 0.9153 0.5592 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5175(6) 0.86698(18) 0.4916(3) 0.0219(7) Uani 1 1 d . . . . .
C5 C 0.5892(7) 0.82583(18) 0.6155(4) 0.0265(7) Uani 1 1 d . . . . .
H5 H 0.5051 0.8275 0.6964 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7730(6) 0.78499(19) 0.6189(4) 0.0266(7) Uani 1 1 d . . . . .
H6 H 0.8190 0.7594 0.7033 0.032 Uiso 1 1 calc R U . . .
C7 C 0.9003(6) 0.77958(17) 0.4972(4) 0.0227(7) Uani 1 1 d . . . . .
C8 C 1.0914(6) 0.73689(17) 0.4920(4) 0.0254(7) Uani 1 1 d . . . . .
H8 H 1.1478 0.7106 0.5736 0.030 Uiso 1 1 calc R U . . .
C9 C 1.1946(6) 0.73383(18) 0.3674(4) 0.0271(7) Uani 1 1 d . . . . .
H9 H 1.3216 0.7049 0.3619 0.033 Uiso 1 1 calc R U . . .
C10 C 1.1118(6) 0.77355(18) 0.2484(4) 0.0233(7) Uani 1 1 d . . . . .
H10 H 1.1843 0.7708 0.1628 0.028 Uiso 1 1 calc R U . . .
C11 C 0.8297(5) 0.81762(16) 0.3732(3) 0.0190(6) Uani 1 1 d . . . . .
C12 C 0.6400(6) 0.86252(15) 0.3705(3) 0.0187(7) Uani 1 1 d . . . . .
C13 C 1.0677(5) 0.90781(17) -0.1141(3) 0.0196(6) Uani 1 1 d . . . . .
C14 C 0.8519(5) 0.95123(16) -0.1568(3) 0.0170(6) Uani 1 1 d . . . . .
H14 H 0.7573 0.9312 -0.2443 0.020 Uiso 1 1 calc R U . . .
C15 C 0.9196(5) 1.01943(17) -0.2006(3) 0.0214(7) Uani 1 1 d . . . . .
H15A H 0.9726 1.0449 -0.1115 0.026 Uiso 1 1 calc R U . . .
H15B H 1.0532 1.0163 -0.2568 0.026 Uiso 1 1 calc R U . . .
C16 C 0.7195(5) 1.05486(16) -0.2909(4) 0.0206(6) Uani 1 1 d . . . . .
C17 C 0.5431(6) 1.08555(19) -0.2287(4) 0.0300(8) Uani 1 1 d . . . . .
H17 H 0.5498 1.0864 -0.1259 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3567(7) 1.1150(2) -0.3165(5) 0.0376(10) Uani 1 1 d . . . . .
H18 H 0.2357 1.1354 -0.2731 0.045 Uiso 1 1 calc R U . . .
C19 C 0.3457(7) 1.11501(19) -0.4661(5) 0.0367(9) Uani 1 1 d . . . . .
H19 H 0.2167 1.1349 -0.5253 0.044 Uiso 1 1 calc R U . . .
C20 C 0.5231(7) 1.0860(2) -0.5296(4) 0.0338(8) Uani 1 1 d . . . . .
H20 H 0.5185 1.0866 -0.6323 0.041 Uiso 1 1 calc R U . . .
C21 C 0.7076(6) 1.05604(18) -0.4419(4) 0.0266(7) Uani 1 1 d . . . . .
H21 H 0.8286 1.0359 -0.4858 0.032 Uiso 1 1 calc R U . . .
O1 O 0.5307(4) 0.80561(13) 0.0009(3) 0.0308(6) Uani 1 1 d . . . . .
H1B H 0.5416 0.7693 -0.0358 0.050 Uiso 1 1 d . . . . .
H1A H 0.4098 0.8205 -0.0350 0.050 Uiso 1 1 d . . . . .
O7 O 0.5527(7) 0.69003(19) -0.1251(5) 0.0668(12) Uani 1 1 d . . . . .
H7A H 0.6579 0.6597 -0.1339 0.050 Uiso 1 1 d . . . . .
H7B H 0.5572 0.6767 -0.0355 0.050 Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.941(2) . ?
Cu1 N3 1.993(3) . ?
Cu1 N2 2.004(3) . ?
Cu1 N1 2.029(3) . ?
Cu1 O1 2.199(3) . ?
O2 C13 1.281(4) . ?
O3 C13 1.232(4) . ?
O4 N4 1.240(5) . ?
O5 N4 1.227(5) . ?
O6 N4 1.230(5) . ?
N1 C1 1.326(4) . ?
N1 C12 1.354(4) . ?
N2 C10 1.323(5) . ?
N2 C11 1.358(4) . ?
N3 C14 1.490(4) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
C1 C2 1.402(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.373(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.410(5) . ?
C3 H3 0.9500 . ?
C4 C12 1.412(4) . ?
C4 C5 1.441(5) . ?
C5 C6 1.348(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.435(5) . ?
C6 H6 0.9500 . ?
C7 C11 1.404(5) . ?
C7 C8 1.414(5) . ?
C8 C9 1.373(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.428(5) . ?
C13 C14 1.536(4) . ?
C14 C15 1.531(4) . ?
C14 H14 1.0000 . ?
C15 C16 1.512(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.389(5) . ?
C16 C21 1.394(5) . ?
C17 C18 1.390(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
O1 H1B 0.8291 . ?
O1 H1A 0.7886 . ?
O7 H7A 0.8821 . ?
O7 H7B 0.8728 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 N3 84.59(10) . . ?
O2 Cu1 N2 92.24(10) . . ?
N3 Cu1 N2 168.26(11) . . ?
O2 Cu1 N1 163.45(10) . . ?
N3 Cu1 N1 97.49(11) . . ?
N2 Cu1 N1 82.41(11) . . ?
O2 Cu1 O1 105.60(11) . . ?
N3 Cu1 O1 98.61(11) . . ?
N2 Cu1 O1 93.13(11) . . ?
N1 Cu1 O1 90.37(11) . . ?
C13 O2 Cu1 116.3(2) . . ?
C1 N1 C12 118.3(3) . . ?
C1 N1 Cu1 130.2(2) . . ?
C12 N1 Cu1 111.3(2) . . ?
C10 N2 C11 118.9(3) . . ?
C10 N2 Cu1 128.7(2) . . ?
C11 N2 Cu1 112.4(2) . . ?
C14 N3 Cu1 110.41(19) . . ?
C14 N3 H3A 109.6 . . ?
Cu1 N3 H3A 109.6 . . ?
C14 N3 H3B 109.6 . . ?
Cu1 N3 H3B 109.6 . . ?
H3A N3 H3B 108.1 . . ?
O6 N4 O5 120.2(4) . . ?
O6 N4 O4 121.1(4) . . ?
O5 N4 O4 118.7(4) . . ?
N1 C1 C2 122.5(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C12 117.1(3) . . ?
C3 C4 C5 124.3(3) . . ?
C12 C4 C5 118.6(3) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C11 C7 C8 117.1(3) . . ?
C11 C7 C6 118.8(3) . . ?
C8 C7 C6 124.1(3) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
N2 C10 C9 122.0(3) . . ?
N2 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
N2 C11 C7 122.9(3) . . ?
N2 C11 C12 116.6(3) . . ?
C7 C11 C12 120.5(3) . . ?
N1 C12 C4 123.1(3) . . ?
N1 C12 C11 117.3(3) . . ?
C4 C12 C11 119.6(3) . . ?
O3 C13 O2 123.5(3) . . ?
O3 C13 C14 119.4(3) . . ?
O2 C13 C14 117.0(3) . . ?
N3 C14 C15 113.8(3) . . ?
N3 C14 C13 109.2(2) . . ?
C15 C14 C13 112.2(3) . . ?
N3 C14 H14 107.1 . . ?
C15 C14 H14 107.1 . . ?
C13 C14 H14 107.1 . . ?
C16 C15 C14 112.9(3) . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C21 118.4(3) . . ?
C17 C16 C15 122.2(3) . . ?
C21 C16 C15 119.4(3) . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.7(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.8(4) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 119.4(4) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C16 121.4(4) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?
Cu1 O1 H1B 132.8 . . ?
Cu1 O1 H1A 115.2 . . ?
H1B O1 H1A 107.0 . . ?
H7A O7 H7B 86.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 0.2(5) . . . . ?
Cu1 N1 C1 C2 175.0(2) . . . . ?
N1 C1 C2 C3 0.9(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C12 -1.1(5) . . . . ?
C2 C3 C4 C5 -179.9(3) . . . . ?
C3 C4 C5 C6 -179.5(3) . . . . ?
C12 C4 C5 C6 1.8(5) . . . . ?
C4 C5 C6 C7 -1.9(5) . . . . ?
C5 C6 C7 C11 -0.1(5) . . . . ?
C5 C6 C7 C8 -178.7(3) . . . . ?
C11 C7 C8 C9 -1.1(5) . . . . ?
C6 C7 C8 C9 177.4(3) . . . . ?
C7 C8 C9 C10 0.9(5) . . . . ?
C11 N2 C10 C9 -1.2(5) . . . . ?
Cu1 N2 C10 C9 178.9(3) . . . . ?
C8 C9 C10 N2 0.2(6) . . . . ?
C10 N2 C11 C7 1.0(5) . . . . ?
Cu1 N2 C11 C7 -179.1(2) . . . . ?
C10 N2 C11 C12 -179.6(3) . . . . ?
Cu1 N2 C11 C12 0.3(3) . . . . ?
C8 C7 C11 N2 0.2(5) . . . . ?
C6 C7 C11 N2 -178.4(3) . . . . ?
C8 C7 C11 C12 -179.2(3) . . . . ?
C6 C7 C11 C12 2.2(5) . . . . ?
C1 N1 C12 C4 -1.8(5) . . . . ?
Cu1 N1 C12 C4 -177.6(2) . . . . ?
C1 N1 C12 C11 179.0(3) . . . . ?
Cu1 N1 C12 C11 3.3(3) . . . . ?
C3 C4 C12 N1 2.3(5) . . . . ?
C5 C4 C12 N1 -178.9(3) . . . . ?
C3 C4 C12 C11 -178.6(3) . . . . ?
C5 C4 C12 C11 0.2(5) . . . . ?
N2 C11 C12 N1 -2.5(4) . . . . ?
C7 C11 C12 N1 177.0(3) . . . . ?
N2 C11 C12 C4 178.4(3) . . . . ?
C7 C11 C12 C4 -2.2(5) . . . . ?
Cu1 O2 C13 O3 173.1(3) . . . . ?
Cu1 O2 C13 C14 -9.8(4) . . . . ?
Cu1 N3 C14 C15 -141.9(2) . . . . ?
Cu1 N3 C14 C13 -15.7(3) . . . . ?
O3 C13 C14 N3 -165.7(3) . . . . ?
O2 C13 C14 N3 17.0(4) . . . . ?
O3 C13 C14 C15 -38.5(4) . . . . ?
O2 C13 C14 C15 144.2(3) . . . . ?
N3 C14 C15 C16 -75.5(3) . . . . ?
C13 C14 C15 C16 159.9(3) . . . . ?
C14 C15 C16 C17 80.6(4) . . . . ?
C14 C15 C16 C21 -98.2(3) . . . . ?
C21 C16 C17 C18 1.7(5) . . . . ?
C15 C16 C17 C18 -177.1(3) . . . . ?
C16 C17 C18 C19 -0.9(6) . . . . ?
C17 C18 C19 C20 -0.7(6) . . . . ?
C18 C19 C20 C21 1.4(6) . . . . ?
C19 C20 C21 C16 -0.5(6) . . . . ?
C17 C16 C21 C20 -1.1(5) . . . . ?
C15 C16 C21 C20 177.8(3) . . . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_D-Isomer
_database_code_depnum_ccdc_archive 'CCDC 1472957'
_audit_update_record             
;
2016-04-08 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        SS12B
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 Cu N4 O7'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Blue
_chemical_formula_weight         505.97

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   'P 21'
_symmetry_int_tables_number      4
_chemical_absolute_configuration rmad

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

_cell_length_a                   5.728(5)
_cell_length_b                   20.587(5)
_cell_length_c                   9.252(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.308(5)
_cell_angle_gamma                90
_cell_volume                     1079.6(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      25.50
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             522
_exptl_absorpt_coefficient_mu    1.064
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.7695
_exptl_absorpt_correction_T_max  0.8568
_exptl_absorpt_process_details   Sadabs

_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  'BRUKER SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12893
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3787
_reflns_number_gt                3579
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0224P)²+0.4479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.027(11)
_refine_ls_number_reflns         3787
_refine_ls_number_parameters     321
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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 0.29423(5) 0.730936(18) 0.59664(3) 0.01211(10) Uani 1 1 d . . .
O1 O 0.5583(3) 0.74049(11) 0.4885(2) 0.0150(5) Uani 1 1 d . . .
O3 O 0.0297(5) 0.80194(14) 0.5032(3) 0.0220(6) Uani 1 1 d . . .
C4 C 0.2203(5) 0.55206(14) 0.2089(3) 0.0139(6) Uani 1 1 d . . .
O6 O 0.5626(5) 0.95268(11) 0.3090(3) 0.0349(6) Uani 1 1 d . . .
C13 C 0.0164(5) 0.73987(17) 0.9915(3) 0.0152(7) Uani 1 1 d . . .
N1 N 0.2035(5) 0.65736(14) 0.4615(3) 0.0133(6) Uani 1 1 d . . .
C14 C 0.0878(6) 0.78080(15) 1.1151(3) 0.0192(7) Uani 1 1 d . . .
H14 H 0.0052 0.7789 1.1945 0.023 Uiso 1 1 calc R . .
C18 C 0.6935(6) 0.87347(15) 0.8683(3) 0.0191(7) Uani 1 1 d . . .
H18 H 0.8173 0.9022 0.8630 0.023 Uiso 1 1 calc R . .
C17 C 0.5907(5) 0.87022(14) 0.9925(3) 0.0176(7) Uani 1 1 d . . .
H17 H 0.6459 0.8960 1.0726 0.021 Uiso 1 1 calc R . .
C6 C 0.0228(6) 0.52113(16) -0.0297(4) 0.0245(8) Uani 1 1 d . . .
H6 H 0.0180 0.5206 -0.1306 0.029 Uiso 1 1 calc R . .
C11 C -0.2248(6) 0.65924(15) 0.8560(3) 0.0172(7) Uani 1 1 d . . .
H11 H -0.3507 0.6303 0.8466 0.021 Uiso 1 1 calc R . .
C5 C 0.2069(6) 0.55080(15) 0.0574(3) 0.0175(7) Uani 1 1 d . . .
H5 H 0.3254 0.5705 0.0141 0.021 Uiso 1 1 calc R . .
C20 C 0.3301(5) 0.78949(14) 0.8739(3) 0.0125(6) Uani 1 1 d . . .
C16 C 0.4001(5) 0.82738(15) 0.9981(3) 0.0149(6) Uani 1 1 d . . .
C10 C -0.0895(5) 0.66565(14) 0.7433(3) 0.0141(7) Uani 1 1 d . . .
H10 H -0.1253 0.6398 0.6607 0.017 Uiso 1 1 calc R . .
C15 C 0.2710(5) 0.82183(15) 1.1194(3) 0.0170(7) Uani 1 1 d . . .
H15 H 0.3149 0.8470 1.2023 0.020 Uiso 1 1 calc R . .
N3 N 0.4367(4) 0.79256(12) 0.7520(3) 0.0140(6) Uani 1 1 d . . .
C8 C -0.1428(6) 0.49197(16) 0.1846(4) 0.0265(8) Uani 1 1 d . . .
H8 H -0.2615 0.4722 0.2275 0.032 Uiso 1 1 calc R . .
N2 N 0.0885(4) 0.70728(12) 0.7492(3) 0.0137(6) Uani 1 1 d . . .
C21 C 0.1399(5) 0.74446(13) 0.8713(3) 0.0128(7) Uani 1 1 d . . .
C19 C 0.6124(5) 0.83358(15) 0.7493(3) 0.0165(7) Uani 1 1 d . . .
H19 H 0.6847 0.8361 0.6657 0.020 Uiso 1 1 calc R . .
C3 C 0.4206(5) 0.58756(15) 0.2992(3) 0.0151(6) Uani 1 1 d . . .
H3A H 0.5517 0.5907 0.2439 0.018 Uiso 1 1 calc R . .
H3B H 0.4731 0.5625 0.3867 0.018 Uiso 1 1 calc R . .
C2 C 0.3538(5) 0.65589(15) 0.3437(3) 0.0121(6) Uani 1 1 d . . .
C9 C 0.0431(6) 0.52088(15) 0.2710(4) 0.0203(7) Uani 1 1 d . . .
H9 H 0.0510 0.5197 0.3721 0.024 Uiso 1 1 calc R . .
C12 C -0.1730(5) 0.69548(15) 0.9810(3) 0.0183(7) Uani 1 1 d . . .
H12 H -0.2610 0.6909 1.0574 0.022 Uiso 1 1 calc R . .
O5 O 0.7182(6) 1.04780(15) 0.3343(3) 0.0550(9) Uani 1 1 d . . .
O4 O 0.3538(5) 1.03356(14) 0.3600(3) 0.0457(8) Uani 1 1 d . . .
N4 N 0.5465(5) 1.01166(14) 0.3348(3) 0.0251(7) Uani 1 1 d . . .
C7 C -0.1554(6) 0.49196(16) 0.0335(4) 0.0257(8) Uani 1 1 d . . .
H7 H -0.2824 0.4725 -0.0246 0.031 Uiso 1 1 calc R . .
C1 C 0.5679(5) 0.69960(15) 0.3848(3) 0.0146(7) Uani 1 1 d . . .
O2 O 0.7355(4) 0.69564(11) 0.3159(2) 0.0179(5) Uani 1 1 d . . .
O1W O 0.0512(6) 0.91740(16) 0.3722(4) 0.0461(8) Uiso 1 1 d D . .
H2N1 H 0.226(6) 0.6234(17) 0.513(4) 0.013(9) Uiso 1 1 d . . .
H1N1 H 0.064(6) 0.6634(16) 0.427(4) 0.013(10) Uiso 1 1 d . . .
H2 H 0.267(6) 0.6758(16) 0.265(4) 0.015(8) Uiso 1 1 d . . .
H1O3 H -0.089(7) 0.7861(19) 0.465(4) 0.028(12) Uiso 1 1 d . . .
H2O3 H 0.051(8) 0.833(3) 0.473(5) 0.041(16) Uiso 1 1 d . . .
H1OW H 0.127(4) 0.9333(13) 0.445(2) 0.000(7) Uiso 1 1 d D . .
H2OW H -0.073(14) 0.927(4) 0.356(9) 0.17(4) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.941(2) . ?
Cu1 N1 1.985(3) . ?
Cu1 N3 2.001(3) . ?
Cu1 N2 2.024(3) . ?
Cu1 O3 2.191(3) . ?
O1 C1 1.283(4) . ?
O3 H1O3 0.79(4) . ?
O3 H2O3 0.72(5) . ?
C4 C9 1.393(4) . ?
C4 C5 1.393(4) . ?
C4 C3 1.507(4) . ?
O6 N4 1.243(4) . ?
C13 C21 1.405(4) . ?
C13 C12 1.411(4) . ?
C13 C14 1.432(4) . ?
N1 C2 1.484(4) . ?
N1 H2N1 0.84(4) . ?
N1 H1N1 0.83(4) . ?
C14 C15 1.343(5) . ?
C14 H14 0.9300 . ?
C18 C17 1.366(4) . ?
C18 C19 1.398(4) . ?
C18 H18 0.9300 . ?
C17 C16 1.410(4) . ?
C17 H17 0.9300 . ?
C6 C5 1.374(5) . ?
C6 C7 1.385(5) . ?
C6 H6 0.9300 . ?
C11 C12 1.372(4) . ?
C11 C10 1.392(4) . ?
C11 H11 0.9300 . ?
C5 H5 0.9300 . ?
C20 N3 1.360(4) . ?
C20 C16 1.398(4) . ?
C20 C21 1.428(4) . ?
C16 C15 1.435(4) . ?
C10 N2 1.327(4) . ?
C10 H10 0.9300 . ?
C15 H15 0.9300 . ?
N3 C19 1.317(4) . ?
C8 C9 1.372(5) . ?
C8 C7 1.389(5) . ?
C8 H8 0.9300 . ?
N2 C21 1.361(4) . ?
C19 H19 0.9300 . ?
C3 C2 1.530(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 C1 1.524(4) . ?
C2 H2 0.92(3) . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
O5 N4 1.234(4) . ?
O4 N4 1.245(4) . ?
C7 H7 0.9300 . ?
C1 O2 1.230(4) . ?
O1W H1OW 0.812(17) . ?
O1W H2OW 0.74(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 84.56(10) . . ?
O1 Cu1 N3 92.22(10) . . ?
N1 Cu1 N3 168.23(11) . . ?
O1 Cu1 N2 163.64(9) . . ?
N1 Cu1 N2 97.45(11) . . ?
N3 Cu1 N2 82.51(11) . . ?
O1 Cu1 O3 105.96(11) . . ?
N1 Cu1 O3 99.06(12) . . ?
N3 Cu1 O3 92.71(11) . . ?
N2 Cu1 O3 89.81(11) . . ?
C1 O1 Cu1 116.09(19) . . ?
Cu1 O3 H1O3 114(3) . . ?
Cu1 O3 H2O3 127(4) . . ?
H1O3 O3 H2O3 112(4) . . ?
C9 C4 C5 118.0(3) . . ?
C9 C4 C3 122.4(3) . . ?
C5 C4 C3 119.6(3) . . ?
C21 C13 C12 117.3(3) . . ?
C21 C13 C14 118.3(3) . . ?
C12 C13 C14 124.3(3) . . ?
C2 N1 Cu1 110.6(2) . . ?
C2 N1 H2N1 110(2) . . ?
Cu1 N1 H2N1 106(2) . . ?
C2 N1 H1N1 111(2) . . ?
Cu1 N1 H1N1 106(2) . . ?
H2N1 N1 H1N1 114(3) . . ?
C15 C14 C13 121.7(3) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C17 C16 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
N3 C20 C16 123.1(3) . . ?
N3 C20 C21 116.7(3) . . ?
C16 C20 C21 120.2(3) . . ?
C20 C16 C17 116.8(3) . . ?
C20 C16 C15 118.6(3) . . ?
C17 C16 C15 124.6(3) . . ?
N2 C10 C11 122.5(3) . . ?
N2 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C14 C15 C16 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C19 N3 C20 118.8(3) . . ?
C19 N3 Cu1 128.8(2) . . ?
C20 N3 Cu1 112.4(2) . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 N2 C21 118.0(3) . . ?
C10 N2 Cu1 130.4(2) . . ?
C21 N2 Cu1 111.44(19) . . ?
N2 C21 C13 123.1(3) . . ?
N2 C21 C20 116.9(2) . . ?
C13 C21 C20 120.0(3) . . ?
N3 C19 C18 122.0(3) . . ?
N3 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C4 C3 C2 113.3(3) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
N1 C2 C1 109.6(3) . . ?
N1 C2 C3 114.2(3) . . ?
C1 C2 C3 112.7(3) . . ?
N1 C2 H2 106(2) . . ?
C1 C2 H2 105(2) . . ?
C3 C2 H2 109(2) . . ?
C8 C9 C4 120.7(3) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
O5 N4 O6 120.5(3) . . ?
O5 N4 O4 120.7(3) . . ?
O6 N4 O4 118.8(3) . . ?
C6 C7 C8 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
O2 C1 O1 123.5(3) . . ?
O2 C1 C2 119.4(3) . . ?
O1 C1 C2 117.0(3) . . ?
H1OW O1W H2OW 116(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 O1 C1 -0.3(2) . . . . ?
N3 Cu1 O1 C1 168.3(2) . . . . ?
N2 Cu1 O1 C1 97.6(4) . . . . ?
O3 Cu1 O1 C1 -98.2(2) . . . . ?
O1 Cu1 N1 C2 -8.5(2) . . . . ?
N3 Cu1 N1 C2 -83.1(6) . . . . ?
N2 Cu1 N1 C2 -172.2(2) . . . . ?
O3 Cu1 N1 C2 96.8(2) . . . . ?
C21 C13 C14 C15 -1.4(4) . . . . ?
C12 C13 C14 C15 179.5(3) . . . . ?
C19 C18 C17 C16 -1.2(5) . . . . ?
C7 C6 C5 C4 0.4(5) . . . . ?
C9 C4 C5 C6 1.4(5) . . . . ?
C3 C4 C5 C6 -177.5(3) . . . . ?
N3 C20 C16 C17 0.0(4) . . . . ?
C21 C20 C16 C17 179.4(3) . . . . ?
N3 C20 C16 C15 178.1(3) . . . . ?
C21 C20 C16 C15 -2.5(4) . . . . ?
C18 C17 C16 C20 1.0(4) . . . . ?
C18 C17 C16 C15 -177.0(3) . . . . ?
C12 C11 C10 N2 -1.7(5) . . . . ?
C13 C14 C15 C16 1.4(5) . . . . ?
C20 C16 C15 C14 0.5(4) . . . . ?
C17 C16 C15 C14 178.5(3) . . . . ?
C16 C20 N3 C19 -0.8(4) . . . . ?
C21 C20 N3 C19 179.7(3) . . . . ?
C16 C20 N3 Cu1 179.3(2) . . . . ?
C21 C20 N3 Cu1 -0.2(3) . . . . ?
O1 Cu1 N3 C19 14.5(3) . . . . ?
N1 Cu1 N3 C19 88.3(6) . . . . ?
N2 Cu1 N3 C19 178.9(3) . . . . ?
O3 Cu1 N3 C19 -91.6(3) . . . . ?
O1 Cu1 N3 C20 -165.6(2) . . . . ?
N1 Cu1 N3 C20 -91.8(6) . . . . ?
N2 Cu1 N3 C20 -1.2(2) . . . . ?
O3 Cu1 N3 C20 88.3(2) . . . . ?
C11 C10 N2 C21 0.5(4) . . . . ?
C11 C10 N2 Cu1 -174.7(2) . . . . ?
O1 Cu1 N2 C10 -110.2(4) . . . . ?
N1 Cu1 N2 C10 -14.1(3) . . . . ?
N3 Cu1 N2 C10 177.7(3) . . . . ?
O3 Cu1 N2 C10 85.0(3) . . . . ?
O1 Cu1 N2 C21 74.3(4) . . . . ?
N1 Cu1 N2 C21 170.43(19) . . . . ?
N3 Cu1 N2 C21 2.30(19) . . . . ?
O3 Cu1 N2 C21 -90.5(2) . . . . ?
C10 N2 C21 C13 1.2(4) . . . . ?
Cu1 N2 C21 C13 177.3(2) . . . . ?
C10 N2 C21 C20 -179.1(3) . . . . ?
Cu1 N2 C21 C20 -3.1(3) . . . . ?
C12 C13 C21 N2 -1.7(4) . . . . ?
C14 C13 C21 N2 179.1(3) . . . . ?
C12 C13 C21 C20 178.7(3) . . . . ?
C14 C13 C21 C20 -0.5(4) . . . . ?
N3 C20 C21 N2 2.2(4) . . . . ?
C16 C20 C21 N2 -177.2(3) . . . . ?
N3 C20 C21 C13 -178.1(3) . . . . ?
C16 C20 C21 C13 2.4(4) . . . . ?
C20 N3 C19 C18 0.6(4) . . . . ?
Cu1 N3 C19 C18 -179.5(2) . . . . ?
C17 C18 C19 N3 0.4(5) . . . . ?
C9 C4 C3 C2 -80.8(4) . . . . ?
C5 C4 C3 C2 98.1(3) . . . . ?
Cu1 N1 C2 C1 14.5(3) . . . . ?
Cu1 N1 C2 C3 142.1(2) . . . . ?
C4 C3 C2 N1 74.7(3) . . . . ?
C4 C3 C2 C1 -159.3(3) . . . . ?
C7 C8 C9 C4 1.4(5) . . . . ?
C5 C4 C9 C8 -2.3(5) . . . . ?
C3 C4 C9 C8 176.6(3) . . . . ?
C10 C11 C12 C13 1.1(4) . . . . ?
C21 C13 C12 C11 0.5(4) . . . . ?
C14 C13 C12 C11 179.6(3) . . . . ?
C5 C6 C7 C8 -1.3(5) . . . . ?
C9 C8 C7 C6 0.4(5) . . . . ?
Cu1 O1 C1 O2 -172.9(2) . . . . ?
Cu1 O1 C1 C2 9.3(3) . . . . ?
N1 C2 C1 O2 166.2(3) . . . . ?
C3 C2 C1 O2 37.8(4) . . . . ?
N1 C2 C1 O1 -15.9(4) . . . . ?
C3 C2 C1 O1 -144.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.061

