# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_TANA_2_2017_B_0m
_database_code_depnum_ccdc_archive 'CCDC 1850127'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C45 H31 Cu N O7), C3 H4 N O, 2(C3 H7 N O), C2 H6 O, 4(O0.50)'
_chemical_formula_sum            'C101 H86 Cu2 N5 O21'
_chemical_formula_weight         1832.82

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'
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

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

_cell_length_a                   22.4236(8)
_cell_length_b                   29.6641(11)
_cell_length_c                   15.5246(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10326.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    149(2)
_cell_measurement_reflns_used    8012
_cell_measurement_theta_min      3.77
_cell_measurement_theta_max      66.59

_exptl_crystal_description       cubic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_F_000             3812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    1.058
_shelx_estimated_absorpt_T_min   0.720
_shelx_estimated_absorpt_T_max   0.756
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7210
_exptl_absorpt_correction_T_max  0.7560
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      149(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44664
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.770
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             9050
_reflns_number_gt                8012
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.969

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] 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_abs_structure_details 
;
 Refined as an inversion twin.
 DMF molecules were refined with the use of 'restrain'
 and 'constrain' command.
 Short distances between protons are consequence of
 operation of double axis symmetry.
;
_refine_ls_abs_structure_Flack   -0.03(7)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         9050
_refine_ls_number_parameters     526
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.1099
_refine_ls_wR_factor_ref         0.3169
_refine_ls_wR_factor_gt          0.2886
_refine_ls_goodness_of_fit_ref   1.449
_refine_ls_restrained_S_all      1.454
_refine_ls_shift/su_max          0.065
_refine_ls_shift/su_mean         0.009

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 0.14321(5) 0.48478(3) -0.07912(6) 0.0508(4) Uani 1 1 d . . . . .
O1 O 0.2047(2) 0.46834(18) 0.0977(4) 0.0601(14) Uani 1 1 d . . . . .
O2 O 0.2074(2) 0.4452(2) -0.0403(4) 0.0577(12) Uani 1 1 d . . . . .
O3 O 0.0804(2) 0.4422(2) -0.0401(4) 0.0596(13) Uani 1 1 d . . . . .
O4 O 0.0789(3) 0.5284(2) -0.0945(4) 0.0611(13) Uani 1 1 d . . . . .
O5 O 0.5732(3) 0.3526(2) 0.1529(5) 0.0728(16) Uani 1 1 d . . . . .
H5 H 0.6068 0.3651 0.1501 0.109 Uiso 1 1 calc R U . . .
O6 O 0.7215(3) 0.3368(2) 0.0795(5) 0.0743(17) Uani 1 1 d . . . . .
H7 H 0.7504 0.3547 0.0768 0.111 Uiso 1 1 calc R U . . .
C1 C 0.2279(3) 0.4469(3) 0.0352(5) 0.0533(16) Uani 1 1 d . . . . .
C2 C 0.2832(4) 0.4211(3) 0.0533(6) 0.0574(18) Uani 1 1 d . . . . .
C3 C 0.3054(4) 0.4155(3) 0.1387(6) 0.062(2) Uani 1 1 d . . . . .
H3 H 0.2839 0.4279 0.1858 0.074 Uiso 1 1 calc R U . . .
C4 C 0.3565(5) 0.3928(3) 0.1535(6) 0.0661(19) Uani 1 1 d . . . . .
H4 H 0.3696 0.3887 0.2111 0.079 Uiso 1 1 calc R U . . .
C5 C 0.3904(4) 0.3753(3) 0.0865(6) 0.0599(18) Uani 1 1 d . . . . .
C6 C 0.4442(4) 0.3503(3) 0.1004(6) 0.063(2) Uani 1 1 d . . . . .
H6 H 0.4580 0.3457 0.1576 0.076 Uiso 1 1 calc R U . . .
C7 C 0.4759(4) 0.3330(3) 0.0335(6) 0.065(2) Uani 1 1 d . . . . .
C8 C 0.4549(4) 0.3403(4) -0.0530(7) 0.079(3) Uani 1 1 d . . . . .
H8 H 0.4773 0.3287 -0.1000 0.094 Uiso 1 1 calc R U . . .
C9 C 0.4042(5) 0.3632(4) -0.0685(7) 0.079(3) Uani 1 1 d . . . . .
H9 H 0.3913 0.3675 -0.1262 0.094 Uiso 1 1 calc R U . . .
C10 C 0.3696(4) 0.3811(3) 0.0005(6) 0.063(2) Uani 1 1 d . . . . .
C11 C 0.3154(4) 0.4037(3) -0.0132(6) 0.0620(19) Uani 1 1 d . . . . .
H11 H 0.3009 0.4070 -0.0704 0.074 Uiso 1 1 calc R U . . .
C12 C 0.5288(4) 0.3031(3) 0.0473(6) 0.063(2) Uani 1 1 d . . . . .
C13 C 0.5743(3) 0.3135(3) 0.1075(6) 0.0588(18) Uani 1 1 d . . . . .
C14 C 0.6210(3) 0.2853(3) 0.1214(6) 0.0575(18) Uani 1 1 d . . . . .
C15 C 0.6243(3) 0.2429(3) 0.0772(6) 0.0565(17) Uani 1 1 d . . . . .
C16 C 0.6695(4) 0.2116(3) 0.0923(8) 0.073(2) Uani 1 1 d . . . . .
H16 H 0.6997 0.2183 0.1332 0.087 Uiso 1 1 calc R U . . .
C17 C 0.6709(4) 0.1708(3) 0.0487(9) 0.084(3) Uani 1 1 d . . . . .
H17 H 0.7007 0.1491 0.0618 0.100 Uiso 1 1 calc R U . . .
C18 C 0.6282(5) 0.1620(3) -0.0144(9) 0.086(3) Uani 1 1 d . . . . .
H18 H 0.6302 0.1344 -0.0454 0.103 Uiso 1 1 calc R U . . .
C19 C 0.5846(4) 0.1912(3) -0.0326(9) 0.080(3) Uani 1 1 d . . . . .
H19 H 0.5563 0.1842 -0.0761 0.096 Uiso 1 1 calc R U . . .
C20 C 0.5804(4) 0.2335(3) 0.0137(6) 0.066(2) Uani 1 1 d . . . . .
C21 C 0.5338(4) 0.2637(3) 0.0002(7) 0.070(2) Uani 1 1 d . . . . .
H21 H 0.5047 0.2572 -0.0426 0.083 Uiso 1 1 calc R U . . .
C22 C 0.6679(4) 0.2955(3) 0.1863(6) 0.0578(18) Uani 1 1 d . . . . .
C23 C 0.7162(4) 0.3206(3) 0.1620(6) 0.0615(19) Uani 1 1 d . . . . .
C24 C 0.7633(4) 0.3309(3) 0.2191(6) 0.066(2) Uani 1 1 d . . . . .
C25 C 0.7588(5) 0.3152(4) 0.3050(7) 0.075(2) Uani 1 1 d . . . . .
H25 H 0.7903 0.3212 0.3445 0.090 Uiso 1 1 calc R U . . .
C26 C 0.7079(5) 0.2906(3) 0.3331(6) 0.070(2) Uani 1 1 d . . . . .
C27 C 0.7005(6) 0.2778(4) 0.4207(9) 0.089(3) Uani 1 1 d . . . . .
H27 H 0.7297 0.2857 0.4623 0.107 Uiso 1 1 calc R U . . .
C28 C 0.6499(6) 0.2534(4) 0.4451(8) 0.088(3) Uani 1 1 d . . . . .
H28 H 0.6459 0.2438 0.5032 0.105 Uiso 1 1 calc R U . . .
C29 C 0.6058(5) 0.2432(4) 0.3867(9) 0.087(3) Uani 1 1 d . . . . .
H29 H 0.5714 0.2270 0.4048 0.105 Uiso 1 1 calc R U . . .
C30 C 0.6115(4) 0.2563(3) 0.3017(7) 0.067(2) Uani 1 1 d . . . . .
H30 H 0.5808 0.2490 0.2621 0.080 Uiso 1 1 calc R U . . .
C31 C 0.6621(4) 0.2804(3) 0.2722(6) 0.0614(19) Uani 1 1 d . . . . .
C32 C 0.8175(5) 0.3562(4) 0.1941(7) 0.077(3) Uani 1 1 d . . . . .
C33 C 0.8395(5) 0.3896(4) 0.2498(8) 0.088(4) Uani 1 1 d . . . . .
H33 H 0.8193 0.3955 0.3024 0.105 Uiso 1 1 calc R U . . .
C34 C 0.8893(5) 0.4137(4) 0.2299(8) 0.090(4) Uani 1 1 d . . . . .
H34 H 0.9029 0.4360 0.2691 0.108 Uiso 1 1 calc R U . . .
C35 C 0.9212(4) 0.4067(4) 0.1533(7) 0.075(3) Uani 1 1 d . . . . .
C36 C 0.9736(5) 0.4297(3) 0.1311(7) 0.073(3) Uani 1 1 d . . . . .
H36 H 0.9893 0.4513 0.1701 0.088 Uiso 1 1 calc R U . . .
C37 C 0.0029(3) 0.4220(3) 0.0551(6) 0.0580(18) Uani 1 1 d . . . . .
C38 C 0.9808(4) 0.3908(3) -0.0047(7) 0.069(2) Uani 1 1 d . . . . .
H38 H 1.0003 0.3862 -0.0582 0.082 Uiso 1 1 calc R U . . .
C39 C 0.9283(4) 0.3664(4) 0.0166(7) 0.074(3) Uani 1 1 d . . . . .
H39 H 0.9138 0.3445 -0.0230 0.089 Uiso 1 1 calc R U . . .
C40 C 0.8978(4) 0.3731(3) 0.0923(7) 0.066(2) Uani 1 1 d . . . . .
C41 C 0.8470(4) 0.3493(3) 0.1171(7) 0.071(2) Uani 1 1 d . . . . .
H41 H 0.8318 0.3271 0.0789 0.085 Uiso 1 1 calc R U . . .
C42 C 0.0592(3) 0.4473(3) 0.0352(6) 0.0580(18) Uani 1 1 d . . . . .
O7 O 0.1464(3) 0.4625(3) -0.2112(4) 0.0805(18) Uani 1 1 d D . . . .
C44 C 0.125(3) 0.467(2) -0.413(5) 0.39(3) Uiso 1 1 d D . . . .
H44A H 0.1646 0.4531 -0.4043 0.592 Uiso 1 1 calc R U . . .
H44B H 0.1298 0.4964 -0.4396 0.592 Uiso 1 1 calc R U . . .
H44C H 0.1018 0.4472 -0.4518 0.592 Uiso 1 1 calc R U . . .
C43 C 0.136(3) 0.488(2) -0.270(4) 0.56(7) Uiso 1 1 d D . . . .
H43 H 0.1550 0.5164 -0.2761 0.672 Uiso 1 1 calc R U . . .
N1 N 0.094(2) 0.471(5) -0.329(3) 2.0(7) Uiso 1 1 d D . . . .
C45 C 0.0427(7) 0.4578(6) -0.2718(12) 0.117(5) Uiso 1 1 d D . . . .
H45A H 0.0561 0.4348 -0.2307 0.176 Uiso 1 1 calc R U . . .
H45B H 0.0103 0.4455 -0.3071 0.176 Uiso 1 1 calc R U . . .
H45C H 0.0284 0.4843 -0.2403 0.176 Uiso 1 1 calc R U . . .
O9 O 0.5000 0.1853(10) 0.7500 0.32(2) Uiso 1 2 d DS . P . .
C53 C 0.5000 0.2281(7) 0.7500 0.105(5) Uiso 1 2 d DS . P . .
H53 H 0.4961 0.2281 0.8142 0.127 Uiso 0.5 1 calc R U P . .
C55 C 0.5330(11) 0.3027(7) 0.7564(17) 0.088(6) Uiso 0.5 1 d D . P . .
O12 O 0.5377(16) 0.4335(13) 0.077(3) 0.176(12) Uiso 0.5 1 d . . P . .
C56 C 0.715(3) 0.319(5) 0.825(3) 2.0(8) Uiso 1 1 d D . . . .
H56 H 0.7537 0.3267 0.8429 2.400 Uiso 1 1 calc R U . . .
O13 O 0.7017(19) 0.3182(14) 0.748(3) 0.35(2) Uiso 1 1 d D . . . .
C58 C 0.613(3) 0.300(3) 0.845(5) 0.58(7) Uiso 1 1 d D . . . .
H58A H 0.6179 0.3004 0.7819 0.875 Uiso 1 1 calc R U . . .
H58B H 0.5855 0.3238 0.8620 0.875 Uiso 1 1 calc R U . . .
H58C H 0.5968 0.2705 0.8621 0.875 Uiso 1 1 calc R U . . .
N4 N 0.672(2) 0.3070(16) 0.887(3) 0.34(2) Uiso 1 1 d D . . . .
C57 C 0.6534(14) 0.3422(11) 0.949(2) 0.189(10) Uiso 1 1 d D . . . .
H57A H 0.6842 0.3458 0.9928 0.283 Uiso 1 1 calc R U . . .
H57B H 0.6157 0.3334 0.9758 0.283 Uiso 1 1 calc R U . . .
H57C H 0.6479 0.3709 0.9180 0.283 Uiso 1 1 calc R U . . .
C54 C 0.603(4) 0.254(2) 0.712(12) 0.61(14) Uiso 0.5 1 d D . P . .
H54A H 0.5971 0.2411 0.6538 0.922 Uiso 0.5 1 calc R U P . .
H54B H 0.6309 0.2350 0.7439 0.922 Uiso 0.5 1 calc R U P . .
H54C H 0.6184 0.2845 0.7070 0.922 Uiso 0.5 1 calc R U P . .
O8 O 0.0000 0.3872(6) 0.7500 0.117(4) Uiso 1 2 d S . P . .
C51 C 0.0517(7) 0.3635(6) 0.7751(11) 0.112(4) Uiso 1 1 d . . . . .
H51A H 0.0421 0.3432 0.8229 0.169 Uiso 1 1 calc R U . . .
H51B H 0.0824 0.3849 0.7934 0.169 Uiso 1 1 calc R U . . .
H51C H 0.0666 0.3458 0.7263 0.169 Uiso 1 1 calc R U . . .
O10 O 0.417(2) 0.503(2) 0.171(4) 0.43(3) Uiso 1 1 d . . . . .
N3 N 0.5465(11) 0.2546(8) 0.756(2) 0.130(9) Uiso 0.5 1 d D . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O4 1.951(5) . ?
Cu1 O2 1.954(6) . ?
Cu1 O1 1.979(5) 2_565 ?
Cu1 O3 1.987(5) . ?
Cu1 O7 2.156(7) . ?
Cu1 Cu1 2.617(2) 2_565 ?
O1 C1 1.271(10) . ?
O1 Cu1 1.979(5) 2_565 ?
O2 C1 1.260(10) . ?
O3 C42 1.270(11) . ?
O4 C42 1.252(11) 2_565 ?
O5 C13 1.357(10) . ?
O5 H5 0.8400 . ?
O6 C23 1.373(12) . ?
O6 H7 0.8400 . ?
C1 C2 1.485(11) . ?
C2 C11 1.361(13) . ?
C2 C3 1.425(13) . ?
C3 C4 1.348(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(13) . ?
C4 H4 0.9500 . ?
C5 C10 1.424(14) . ?
C5 C6 1.432(12) . ?
C6 C7 1.360(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.439(15) . ?
C7 C12 1.497(13) . ?
C8 C9 1.347(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.425(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.406(13) . ?
C11 H11 0.9500 . ?
C12 C21 1.382(13) . ?
C12 C13 1.417(13) . ?
C13 C14 1.359(12) . ?
C14 C15 1.433(11) . ?
C14 C22 1.490(13) . ?
C15 C16 1.393(13) . ?
C15 C20 1.422(14) . ?
C16 C17 1.387(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.395(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.336(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.450(13) . ?
C19 H19 0.9500 . ?
C20 C21 1.393(14) . ?
C21 H21 0.9500 . ?
C22 C23 1.368(12) . ?
C22 C31 1.413(13) . ?
C23 C24 1.411(14) . ?
C24 C25 1.417(15) . ?
C24 C32 1.480(12) . ?
C25 C26 1.425(14) . ?
C25 H25 0.9500 . ?
C26 C27 1.421(16) . ?
C26 C31 1.427(14) . ?
C27 C28 1.396(17) . ?
C27 H27 0.9500 . ?
C28 C29 1.376(19) . ?
C28 H28 0.9500 . ?
C29 C30 1.380(16) . ?
C29 H29 0.9500 . ?
C30 C31 1.418(12) . ?
C30 H30 0.9500 . ?
C32 C41 1.381(13) . ?
C32 C33 1.406(14) . ?
C33 C34 1.361(14) . ?
C33 H33 0.9500 . ?
C34 C35 1.403(14) . ?
C34 H34 0.9500 . ?
C35 C36 1.402(13) . ?
C35 C40 1.471(12) . ?
C36 C37 1.371(13) 1_655 ?
C36 H36 0.9500 . ?
C37 C36 1.371(13) 1_455 ?
C37 C38 1.401(13) 1_455 ?
C37 C42 1.500(11) . ?
C38 C37 1.401(13) 1_655 ?
C38 C39 1.421(13) . ?
C38 H38 0.9500 . ?
C39 C40 1.375(14) . ?
C39 H39 0.9500 . ?
C40 C41 1.392(12) . ?
C41 H41 0.9500 . ?
C42 O4 1.252(11) 2_565 ?
O7 C43 1.20(3) . ?
C44 N1 1.50(3) . ?
C44 H44A 1.0637 . ?
C44 H44B 1.0551 . ?
C44 H44C 1.0525 . ?
C43 N1 1.41(3) . ?
C43 H43 0.9500 . ?
N1 C45 1.50(3) . ?
C45 C45 2.03(3) 3_554 ?
C45 H45A 0.9893 . ?
C45 H45B 0.9868 . ?
C45 H45C 0.9977 . ?
O9 C53 1.27(2) . ?
C53 N3 1.31(2) . ?
C53 N3 1.31(2) 3_656 ?
C53 H53 1.0000 . ?
C55 N3 1.46(2) . ?
C55 C55 1.49(5) 3_656 ?
C55 C58 2.26(7) . ?
C56 O13 1.23(3) . ?
C56 N4 1.39(3) . ?
C56 H56 0.9500 . ?
C58 N4 1.49(3) . ?
C58 H58A 1.1110 . ?
C58 H58B 1.0681 . ?
C58 H58C 1.1079 . ?
N4 C57 1.48(3) . ?
C57 H57A 0.9803 . ?
C57 H57B 0.9803 . ?
C57 H57C 0.9802 . ?
C54 N3 1.44(3) . ?
C54 H54A 1.0393 . ?
C54 H54B 1.0410 . ?
C54 H54C 1.0440 . ?
O8 C51 1.411(18) 3_556 ?
O8 C51 1.411(18) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cu1 O2 168.8(2) . . ?
O4 Cu1 O1 91.8(2) . 2_565 ?
O2 Cu1 O1 87.4(2) . 2_565 ?
O4 Cu1 O3 86.3(3) . . ?
O2 Cu1 O3 92.6(2) . . ?
O1 Cu1 O3 170.1(3) 2_565 . ?
O4 Cu1 O7 96.4(3) . . ?
O2 Cu1 O7 94.8(3) . . ?
O1 Cu1 O7 93.1(3) 2_565 . ?
O3 Cu1 O7 96.8(3) . . ?
O4 Cu1 Cu1 83.47(17) . 2_565 ?
O2 Cu1 Cu1 85.30(18) . 2_565 ?
O1 Cu1 Cu1 83.94(18) 2_565 2_565 ?
O3 Cu1 Cu1 86.17(18) . 2_565 ?
O7 Cu1 Cu1 177.0(2) . 2_565 ?
C1 O1 Cu1 121.7(5) . 2_565 ?
C1 O2 Cu1 122.1(5) . . ?
C42 O3 Cu1 118.0(5) . . ?
C42 O4 Cu1 123.6(5) 2_565 . ?
C13 O5 H5 109.4 . . ?
C23 O6 H7 109.5 . . ?
O1 C1 O2 125.5(7) . . ?
O1 C1 C2 117.1(7) . . ?
O2 C1 C2 117.3(7) . . ?
C11 C2 C3 118.4(8) . . ?
C11 C2 C1 119.7(8) . . ?
C3 C2 C1 121.8(8) . . ?
C4 C3 C2 120.9(8) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 121.6(8) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C10 118.5(8) . . ?
C4 C5 C6 122.8(9) . . ?
C10 C5 C6 118.6(8) . . ?
C7 C6 C5 121.4(8) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 119.0(8) . . ?
C6 C7 C12 121.9(8) . . ?
C8 C7 C12 118.8(8) . . ?
C9 C8 C7 121.3(9) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.9(9) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C5 118.9(8) . . ?
C11 C10 C9 122.3(9) . . ?
C5 C10 C9 118.8(8) . . ?
C10 C11 C2 121.6(8) . . ?
C10 C11 H11 119.2 . . ?
C2 C11 H11 119.2 . . ?
C21 C12 C13 118.4(8) . . ?
C21 C12 C7 119.3(8) . . ?
C13 C12 C7 122.3(7) . . ?
C14 C13 O5 117.3(8) . . ?
C14 C13 C12 121.6(8) . . ?
O5 C13 C12 121.1(8) . . ?
C13 C14 C15 120.4(8) . . ?
C13 C14 C22 121.7(7) . . ?
C15 C14 C22 117.8(7) . . ?
C16 C15 C14 122.8(9) . . ?
C16 C15 C20 119.3(8) . . ?
C14 C15 C20 117.9(7) . . ?
C17 C16 C15 121.1(10) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 119.3(10) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 122.0(9) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C18 C19 C20 120.3(11) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C15 119.9(8) . . ?
C21 C20 C19 122.1(9) . . ?
C15 C20 C19 117.9(9) . . ?
C12 C21 C20 121.6(9) . . ?
C12 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C23 C22 C31 120.4(8) . . ?
C23 C22 C14 119.0(8) . . ?
C31 C22 C14 120.6(7) . . ?
O6 C23 C22 121.1(9) . . ?
O6 C23 C24 116.5(7) . . ?
C22 C23 C24 122.4(9) . . ?
C25 C24 C23 117.9(8) . . ?
C25 C24 C32 118.1(9) . . ?
C23 C24 C32 123.9(9) . . ?
C24 C25 C26 120.9(9) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.6 . . ?
C27 C26 C31 119.6(9) . . ?
C27 C26 C25 121.6(10) . . ?
C31 C26 C25 118.8(9) . . ?
C28 C27 C26 119.5(12) . . ?
C28 C27 H27 120.3 . . ?
C26 C27 H27 120.2 . . ?
C29 C28 C27 121.2(11) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.3 . . ?
C30 C29 C28 120.0(9) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C31 121.7(10) . . ?
C29 C30 H30 119.2 . . ?
C31 C30 H30 119.1 . . ?
C30 C31 C22 122.6(9) . . ?
C30 C31 C26 117.9(8) . . ?
C22 C31 C26 119.5(8) . . ?
C41 C32 C33 117.9(8) . . ?
C41 C32 C24 123.1(8) . . ?
C33 C32 C24 119.0(8) . . ?
C34 C33 C32 121.2(9) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C33 C34 C35 122.1(9) . . ?
C33 C34 H34 118.9 . . ?
C35 C34 H34 119.0 . . ?
C34 C35 C36 124.2(8) . . ?
C34 C35 C40 117.7(8) . . ?
C36 C35 C40 118.1(8) . . ?
C37 C36 C35 122.2(9) 1_655 . ?
C37 C36 H36 118.9 1_655 . ?
C35 C36 H36 118.9 . . ?
C36 C37 C38 120.6(8) 1_455 1_455 ?
C36 C37 C42 119.9(8) 1_455 . ?
C38 C37 C42 119.4(7) 1_455 . ?
C37 C38 C39 118.5(8) 1_655 . ?
C37 C38 H38 120.8 1_655 . ?
C39 C38 H38 120.7 . . ?
C40 C39 C38 122.5(8) . . ?
C40 C39 H39 118.8 . . ?
C38 C39 H39 118.7 . . ?
C39 C40 C41 124.8(8) . . ?
C39 C40 C35 118.0(8) . . ?
C41 C40 C35 117.2(8) . . ?
C32 C41 C40 123.8(8) . . ?
C32 C41 H41 118.1 . . ?
C40 C41 H41 118.1 . . ?
O4 C42 O3 127.9(7) 2_565 . ?
O4 C42 C37 115.7(7) 2_565 . ?
O3 C42 C37 116.4(8) . . ?
C43 O7 Cu1 122(5) . . ?
N1 C44 H44A 115.6 . . ?
N1 C44 H44B 121.3 . . ?
H44A C44 H44B 101.1 . . ?
N1 C44 H44C 113.7 . . ?
H44A C44 H44C 100.7 . . ?
H44B C44 H44C 101.5 . . ?
O7 C43 N1 113(4) . . ?
O7 C43 H43 120.8 . . ?
N1 C43 H43 125.7 . . ?
C43 N1 C45 103(3) . . ?
C43 N1 C44 106(3) . . ?
C45 N1 C44 149(7) . . ?
N1 C45 C45 156(4) . 3_554 ?
N1 C45 H45A 109.1 . . ?
C45 C45 H45A 94.5 3_554 . ?
N1 C45 H45B 106.4 . . ?
C45 C45 H45B 63.2 3_554 . ?
H45A C45 H45B 108.3 . . ?
N1 C45 H45C 116.0 . . ?
C45 C45 H45C 55.3 3_554 . ?
H45A C45 H45C 107.2 . . ?
H45B C45 H45C 109.6 . . ?
O9 C53 N3 127.0(13) . . ?
O9 C53 N3 127.0(13) . 3_656 ?
N3 C53 N3 106(3) . 3_656 ?
O9 C53 H53 90.0 . . ?
N3 C53 H53 89.9 . . ?
N3 C53 H53 90.1 3_656 . ?
N3 C55 C55 101.8(14) . 3_656 ?
N3 C55 C58 79(3) . . ?
C55 C55 C58 150(3) 3_656 . ?
O13 C56 N4 120(5) . . ?
O13 C56 H56 120.2 . . ?
N4 C56 H56 119.6 . . ?
N4 C58 C55 165(7) . . ?
N4 C58 H58A 122.4 . . ?
C55 C58 H58A 46.5 . . ?
N4 C58 H58B 116.7 . . ?
C55 C58 H58B 63.0 . . ?
H58A C58 H58B 100.5 . . ?
N4 C58 H58C 124.2 . . ?
C55 C58 H58C 70.2 . . ?
H58A C58 H58C 94.0 . . ?
H58B C58 H58C 92.6 . . ?
C56 N4 C58 110(4) . . ?
C56 N4 C57 118(5) . . ?
C58 N4 C57 98(2) . . ?
N4 C57 H57A 110.0 . . ?
N4 C57 H57B 110.3 . . ?
H57A C57 H57B 109.5 . . ?
N4 C57 H57C 108.2 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.4 . . ?
N3 C54 H54A 115.6 . . ?
N3 C54 H54B 115.8 . . ?
H54A C54 H54B 102.7 . . ?
N3 C54 H54C 116.6 . . ?
H54A C54 H54C 101.2 . . ?
H54B C54 H54C 102.8 . . ?
C51 O8 C51 120.2(18) 3_556 . ?
O8 C51 H51A 109.5 . . ?
O8 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
O8 C51 H51C 109.4 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C53 N3 C54 131(5) . . ?
C53 N3 C55 115(2) . . ?
C54 N3 C55 102(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 O2 -15.7(11) 2_565 . . . ?
Cu1 O1 C1 C2 165.2(5) 2_565 . . . ?
Cu1 O2 C1 O1 11.3(11) . . . . ?
Cu1 O2 C1 C2 -169.6(5) . . . . ?
O1 C1 C2 C11 -169.1(8) . . . . ?
O2 C1 C2 C11 11.8(11) . . . . ?
O1 C1 C2 C3 8.1(11) . . . . ?
O2 C1 C2 C3 -171.0(8) . . . . ?
C11 C2 C3 C4 -1.2(14) . . . . ?
C1 C2 C3 C4 -178.5(8) . . . . ?
C2 C3 C4 C5 2.0(15) . . . . ?
C3 C4 C5 C10 -1.0(14) . . . . ?
C3 C4 C5 C6 -178.7(9) . . . . ?
C4 C5 C6 C7 179.0(10) . . . . ?
C10 C5 C6 C7 1.4(14) . . . . ?
C5 C6 C7 C8 0.3(15) . . . . ?
C5 C6 C7 C12 -173.9(8) . . . . ?
C6 C7 C8 C9 -1.0(17) . . . . ?
C12 C7 C8 C9 173.3(10) . . . . ?
C7 C8 C9 C10 0.1(18) . . . . ?
C4 C5 C10 C11 -0.7(13) . . . . ?
C6 C5 C10 C11 177.1(8) . . . . ?
C4 C5 C10 C9 180.0(10) . . . . ?
C6 C5 C10 C9 -2.3(13) . . . . ?
C8 C9 C10 C11 -177.7(10) . . . . ?
C8 C9 C10 C5 1.6(16) . . . . ?
C5 C10 C11 C2 1.4(14) . . . . ?
C9 C10 C11 C2 -179.2(10) . . . . ?
C3 C2 C11 C10 -0.5(13) . . . . ?
C1 C2 C11 C10 176.8(8) . . . . ?
C6 C7 C12 C21 133.2(10) . . . . ?
C8 C7 C12 C21 -41.0(13) . . . . ?
C6 C7 C12 C13 -46.7(13) . . . . ?
C8 C7 C12 C13 139.1(10) . . . . ?
C21 C12 C13 C14 -2.1(13) . . . . ?
C7 C12 C13 C14 177.8(8) . . . . ?
C21 C12 C13 O5 177.0(8) . . . . ?
C7 C12 C13 O5 -3.1(13) . . . . ?
O5 C13 C14 C15 178.6(7) . . . . ?
C12 C13 C14 C15 -2.2(12) . . . . ?
O5 C13 C14 C22 2.6(11) . . . . ?
C12 C13 C14 C22 -178.2(8) . . . . ?
C13 C14 C15 C16 -176.5(8) . . . . ?
C22 C14 C15 C16 -0.3(11) . . . . ?
C13 C14 C15 C20 5.2(11) . . . . ?
C22 C14 C15 C20 -178.6(7) . . . . ?
C14 C15 C16 C17 179.5(9) . . . . ?
C20 C15 C16 C17 -2.3(13) . . . . ?
C15 C16 C17 C18 3.3(15) . . . . ?
C16 C17 C18 C19 -2.1(17) . . . . ?
C17 C18 C19 C20 -0.1(16) . . . . ?
C16 C15 C20 C21 177.7(8) . . . . ?
C14 C15 C20 C21 -4.0(12) . . . . ?
C16 C15 C20 C19 0.1(12) . . . . ?
C14 C15 C20 C19 178.4(7) . . . . ?
C18 C19 C20 C21 -176.4(10) . . . . ?
C18 C19 C20 C15 1.1(14) . . . . ?
C13 C12 C21 C20 3.4(14) . . . . ?
C7 C12 C21 C20 -176.5(8) . . . . ?
C15 C20 C21 C12 -0.3(13) . . . . ?
C19 C20 C21 C12 177.2(9) . . . . ?
C13 C14 C22 C23 -88.2(10) . . . . ?
C15 C14 C22 C23 95.7(9) . . . . ?
C13 C14 C22 C31 90.6(10) . . . . ?
C15 C14 C22 C31 -85.5(9) . . . . ?
C31 C22 C23 O6 -177.9(8) . . . . ?
C14 C22 C23 O6 0.8(12) . . . . ?
C31 C22 C23 C24 2.8(13) . . . . ?
C14 C22 C23 C24 -178.5(8) . . . . ?
O6 C23 C24 C25 179.3(9) . . . . ?
C22 C23 C24 C25 -1.3(13) . . . . ?
O6 C23 C24 C32 -2.2(13) . . . . ?
C22 C23 C24 C32 177.2(9) . . . . ?
C23 C24 C25 C26 -1.3(15) . . . . ?
C32 C24 C25 C26 -179.9(9) . . . . ?
C24 C25 C26 C27 -174.7(11) . . . . ?
C24 C25 C26 C31 2.4(15) . . . . ?
C31 C26 C27 C28 3.2(17) . . . . ?
C25 C26 C27 C28 -179.7(11) . . . . ?
C26 C27 C28 C29 -2.7(19) . . . . ?
C27 C28 C29 C30 1.1(19) . . . . ?
C28 C29 C30 C31 0.0(18) . . . . ?
C29 C30 C31 C22 -177.7(10) . . . . ?
C29 C30 C31 C26 0.6(14) . . . . ?
C23 C22 C31 C30 176.7(8) . . . . ?
C14 C22 C31 C30 -2.0(12) . . . . ?
C23 C22 C31 C26 -1.5(12) . . . . ?
C14 C22 C31 C26 179.7(8) . . . . ?
C27 C26 C31 C30 -2.1(14) . . . . ?
C25 C26 C31 C30 -179.3(9) . . . . ?
C27 C26 C31 C22 176.2(10) . . . . ?
C25 C26 C31 C22 -1.0(13) . . . . ?
C25 C24 C32 C41 137.2(12) . . . . ?
C23 C24 C32 C41 -41.3(17) . . . . ?
C25 C24 C32 C33 -44.4(16) . . . . ?
C23 C24 C32 C33 137.1(12) . . . . ?
C41 C32 C33 C34 -2(2) . . . . ?
C24 C32 C33 C34 179.8(13) . . . . ?
C32 C33 C34 C35 0(2) . . . . ?
C33 C34 C35 C36 -178.1(14) . . . . ?
C33 C34 C35 C40 2(2) . . . . ?
C34 C35 C36 C37 -179.3(13) . . . 1_655 ?
C40 C35 C36 C37 0.5(18) . . . 1_655 ?
C37 C38 C39 C40 1.9(17) 1_655 . . . ?
C38 C39 C40 C41 -178.5(11) . . . . ?
C38 C39 C40 C35 -0.6(17) . . . . ?
C34 C35 C40 C39 179.2(12) . . . . ?
C36 C35 C40 C39 -0.6(17) . . . . ?
C34 C35 C40 C41 -2.7(18) . . . . ?
C36 C35 C40 C41 177.5(10) . . . . ?
C33 C32 C41 C40 1.0(19) . . . . ?
C24 C32 C41 C40 179.5(11) . . . . ?
C39 C40 C41 C32 179.1(12) . . . . ?
C35 C40 C41 C32 1.2(17) . . . . ?
Cu1 O3 C42 O4 -12.0(12) . . . 2_565 ?
Cu1 O3 C42 C37 166.2(6) . . . . ?
C36 C37 C42 O4 5.9(13) 1_455 . . 2_565 ?
C38 C37 C42 O4 -174.2(9) 1_455 . . 2_565 ?
C36 C37 C42 O3 -172.5(9) 1_455 . . . ?
C38 C37 C42 O3 7.4(13) 1_455 . . . ?
Cu1 O7 C43 N1 -129(5) . . . . ?
O7 C43 N1 C45 51(8) . . . . ?
O7 C43 N1 C44 -118(10) . . . . ?
C43 N1 C45 C45 123(7) . . . 3_554 ?
C44 N1 C45 C45 -77(27) . . . 3_554 ?
O13 C56 N4 C58 -5(14) . . . . ?
O13 C56 N4 C57 -116(11) . . . . ?
C55 C58 N4 C56 -31(19) . . . . ?
C55 C58 N4 C57 93(18) . . . . ?
O9 C53 N3 C54 47(9) . . . . ?
N3 C53 N3 C54 -133(9) 3_656 . . . ?
O9 C53 N3 C55 -178.5(16) . . . . ?
N3 C53 N3 C55 1.5(16) 3_656 . . . ?
C55 C55 N3 C53 -4(4) 3_656 . . . ?
C58 C55 N3 C53 146(3) . . . . ?
C55 C55 N3 C54 143(8) 3_656 . . . ?
C58 C55 N3 C54 -67(8) . . . . ?

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
C54 H54C O13 1.04 2.14 2.98(11) 136.4 .
C58 H58C N3 1.11 1.82 2.43(5) 110.1 .
C45 H45C N1 1.00 2.86 3.46(5) 119.2 3_554
C43 H43 O1 0.95 2.99 3.35(7) 104.0 2_565
C54 H54C O13 1.04 2.14 2.98(11) 136.4 .
C57 H57A O6 0.98 1.61 2.55(3) 159.3 1_556
C58 H58C N3 1.11 1.82 2.43(5) 110.1 .
C54 H54C O13 1.04 2.14 2.98(11) 136.4 .
C57 H57A O6 0.98 1.61 2.55(3) 159.3 1_556
C58 H58C N3 1.11 1.82 2.43(5) 110.1 .
C45 H45A O8 0.99 1.92 2.33(2) 101.6 1_554
C54 H54C O13 1.04 2.14 2.98(11) 136.4 .
C58 H58C N3 1.11 1.82 2.43(5) 110.1 .
C45 H45C N1 1.00 2.86 3.46(5) 119.2 3_554
C43 H43 O1 0.95 2.99 3.35(7) 104.0 2_565
C54 H54C O13 1.04 2.14 2.98(11) 136.4 .
C57 H57A O6 0.98 1.61 2.55(3) 159.3 1_556
C45 H45A O8 0.99 1.92 2.33(2) 101.6 1_554
C54 H54C O13 1.04 2.14 2.98(11) 136.4 .
C57 H57A O6 0.98 1.61 2.55(3) 159.3 1_556
C45 H45A O8 0.99 1.92 2.33(2) 101.6 1_554
C45 H45C N1 1.00 2.86 3.46(5) 119.2 3_554
C57 H57A O6 0.98 1.61 2.55(3) 159.3 1_556
C54 H54C O13 1.04 2.14 2.98(11) 136.4 .
C45 H45A O8 0.99 1.92 2.33(2) 101.6 1_554
C57 H57A O6 0.98 1.61 2.55(3) 159.3 1_556
C54 H54C O13 1.04 2.14 2.98(11) 136.4 .
C45 H45A O8 0.99 1.92 2.33(2) 101.6 1_554
C58 H58C N3 1.11 1.82 2.43(5) 110.1 .
C57 H57A O6 0.98 1.61 2.55(3) 159.3 1_556
C54 H54C O13 1.04 2.14 2.98(11) 136.4 .
C57 H57A O6 0.98 1.61 2.55(3) 159.3 1_556
C54 H54C O13 1.04 2.14 2.98(11) 136.4 .
C43 H43 O1 0.95 2.99 3.35(7) 104.0 2_565
C45 H45C N1 1.00 2.86 3.46(5) 119.2 3_554
C57 H57A O6 0.98 1.61 2.55(3) 159.3 1_556

_refine_diff_density_max         1.375
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.166

_shelxl_version_number           2014-3

