# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_I
_audit_block_doi                 10.5517/cc1j59xx
_database_code_depnum_ccdc_archive 'CCDC 1405289'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-09-28 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H26 Cu N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         646.17
_chemical_absolute_configuration syn

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   15.2618(6)
_cell_length_b                   13.0327(5)
_cell_length_c                   17.7452(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.0781(12)
_cell_angle_gamma                90
_cell_volume                     3355.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    93.(2)

_exptl_crystal_description       columun
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1332

_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
;
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            23913
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             11568
_reflns_number_gt                10939
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_gt          0.1798
_refine_ls_wR_factor_ref         0.1826
_refine_ls_goodness_of_fit_ref   1.507
_refine_ls_restrained_S_all      1.507
_refine_ls_number_reflns         11568
_refine_ls_number_parameters     876
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.510
_refine_diff_density_min         -0.539
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 4862 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.018(3)

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'

_computing_data_collection       'Bruker SMART APEXII'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1'
_computing_publication_material  'General Report'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.74956(5) 0.06288(6) 0.56234(5) 0.0147(2) Uani d . . . 1 . .
Cu Cu2 0.42933(5) 0.32866(6) 0.61327(5) 0.0145(2) Uani d . . . 1 . .
N N2 0.6455(4) 0.0826(4) 0.6041(3) 0.0149(12) Uani d . . . 1 . .
C C9 0.4776(5) 0.0856(5) 0.5574(4) 0.0162(14) Uani d . . . 1 . .
C C1 0.5852(5) 0.0702(7) 0.3170(5) 0.0266(17) Uani d . . . 1 . .
H H1 0.5931 0.0677 0.266 0.032 Uiso calc U . R 1 . .
N N1 0.6534(4) 0.0738(5) 0.4580(3) 0.0186(12) Uani d . . . 1 . .
C C12 0.5617(5) 0.0872(5) 0.6963(4) 0.0208(15) Uani d . . . 1 . .
H H12 0.5616 0.0874 0.7498 0.025 Uiso calc U . R 1 . .
C C5 0.4977(6) 0.0747(6) 0.3251(4) 0.0254(17) Uani d . . . 1 . .
H H5 0.4452 0.0753 0.2791 0.031 Uiso calc U . R 1 . .
C C4 0.5674(5) 0.0788(5) 0.4663(4) 0.0161(14) Uani d . . . 1 . .
C C2 0.6601(5) 0.0693(6) 0.3846(4) 0.0190(14) Uani d . . . 1 . .
H H2 0.7199 0.0652 0.3788 0.023 Uiso calc U . R 1 . .
C C6 0.4860(5) 0.0785(5) 0.4003(4) 0.0177(15) Uani d . . . 1 . .
C C7 0.3994(5) 0.0808(6) 0.4158(5) 0.0241(17) Uani d . . . 1 . .
H H7 0.3438 0.0804 0.3728 0.029 Uiso calc U . R 1 . .
C C10 0.5625(5) 0.0820(5) 0.5446(4) 0.0151(14) Uani d . . . 1 . .
C C14 0.6456(4) 0.0855(5) 0.6808(4) 0.0138(14) Uani d . . . 1 . .
C C11 0.4797(5) 0.0887(5) 0.6371(4) 0.0182(15) Uani d . . . 1 . .
H H11 0.4237 0.0918 0.6497 0.022 Uiso calc U . R 1 . .
C C8 0.3959(5) 0.0836(6) 0.4905(4) 0.0208(15) Uani d . . . 1 . .
H H8 0.3375 0.0843 0.4992 0.025 Uiso calc U . R 1 . .
C C23 0.8214(5) 0.0591(6) 0.7317(4) 0.0164(14) Uani d . . . 1 . .
C C22 0.9013(4) 0.0561(6) 0.7977(4) 0.0150(13) Uani d . . . 1 . .
C C18 0.9806(5) 0.0695(7) 0.9435(4) 0.0238(15) Uani d . . . 1 . .
H H18 1.0375 0.0476 0.9376 0.029 Uiso calc U . R 1 . .
C C24 0.7345(5) 0.0846(5) 0.7444(4) 0.0153(14) Uani d . . . 1 . .
C C20 0.8149(5) 0.1053(6) 0.8878(4) 0.0193(15) Uani d . . . 1 . .
C C19 0.8997(4) 0.0754(6) 0.8751(4) 0.0174(14) Uani d . . . 1 . .
C C15 0.8918(5) 0.1266(6) 1.0269(5) 0.0271(18) Uani d . . . 1 . .
H H15 0.8898 0.1441 1.0784 0.032 Uiso calc U . R 1 . .
C C17 0.9760(5) 0.0952(6) 1.0163(4) 0.0272(18) Uani d . . . 1 . .
H H17 1.0301 0.0921 1.0608 0.033 Uiso calc U . R 1 . .
C C21 0.7359(5) 0.1100(5) 0.8223(4) 0.0179(15) Uani d . . . 1 . .
H H21 0.68 0.1314 0.8303 0.021 Uiso calc U . R 1 . .
C C16 0.8139(5) 0.1317(6) 0.9639(5) 0.0263(17) Uani d . . . 1 . .
H H16 0.7579 0.1536 0.9716 0.032 Uiso calc U . R 1 . .
C C26 1.0156(5) -0.0718(6) 0.7762(4) 0.0168(15) Uani d . . . 1 . .
C C25 1.0945(5) -0.0967(6) 0.7533(4) 0.0203(16) Uani d . . . 1 . .
C C29 1.1176(5) -0.2004(6) 0.7475(4) 0.0254(17) Uani d . . . 1 . .
H H29 1.171 -0.2164 0.7332 0.03 Uiso calc U . R 1 . .
C C30 1.0659(6) -0.2780(6) 0.7617(5) 0.0270(18) Uani d . . . 1 . .
H H30 1.0821 -0.3473 0.756 0.032 Uiso calc U . R 1 . .
C C27 0.9628(5) -0.1568(6) 0.7923(4) 0.0216(15) Uani d . . . 1 . .
H H27 0.9099 -0.1435 0.8082 0.026 Uiso calc U . R 1 . .
C C28 0.9881(6) -0.2551(6) 0.7850(5) 0.0259(18) Uani d . . . 1 . .
H H28 0.9525 -0.3096 0.7959 0.031 Uiso calc U . R 1 . .
C C34 0.9894(5) 0.0306(6) 0.7803(4) 0.0170(15) Uani d . . . 1 . .
C C33 1.0397(5) 0.1107(6) 0.7619(4) 0.0195(15) Uani d . . . 1 . .
C C31 1.1441(5) -0.0140(6) 0.7338(5) 0.0247(17) Uani d . . . 1 . .
H H31 1.1959 -0.0283 0.7167 0.03 Uiso calc U . R 1 . .
C C32 1.1190(5) 0.0855(6) 0.7391(5) 0.0244(17) Uani d . . . 1 . .
H H32 1.1551 0.1391 0.7275 0.029 Uiso calc U . R 1 . .
C C37 1.0137(5) 0.2193(6) 0.7636(5) 0.0260(18) Uani d . . . 1 . .
C C36 1.0235(7) 0.2701(7) 0.8362(7) 0.040(2) Uani d . . . 1 . .
H H36 1.0438 0.2335 0.8848 0.048 Uiso calc U . R 1 . .
C C38 0.9818(5) 0.2744(7) 0.6935(6) 0.0307(19) Uani d . . . 1 . .
H H38 0.9725 0.2408 0.6442 0.037 Uiso calc U . R 1 . .
C C39 0.9634(6) 0.3778(7) 0.6952(8) 0.046(3) Uani d . . . 1 . .
H H39 0.9435 0.4149 0.6468 0.055 Uiso calc U . R 1 . .
C C35 1.0035(8) 0.3716(7) 0.8356(8) 0.056(3) Uani d . . . 1 . .
H H35 1.0104 0.405 0.8847 0.067 Uiso calc U . R 1 . .
C C44 0.5602(5) 0.3293(7) 0.3767(4) 0.0241(16) Uani d . . . 1 . .
H H44 0.5599 0.3279 0.323 0.029 Uiso calc U . R 1 . .
C C40 0.3174(5) 0.3300(7) 0.4405(4) 0.0215(15) Uani d . . . 1 . .
H H40 0.2633 0.3314 0.4561 0.026 Uiso calc U . R 1 . .
C C49 0.6360(4) 0.3363(5) 0.6732(4) 0.0150(13) Uani d . . . 1 . .
C C48 0.7268(5) 0.3306(6) 0.5826(4) 0.0198(15) Uani d . . . 1 . .
H H48 0.7851 0.327 0.5739 0.024 Uiso calc U . R 1 . .
C C51 0.4776(5) 0.3299(5) 0.4731(4) 0.0162(14) Uani d . . . 1 . .
C C46 0.6448(5) 0.3317(6) 0.5168(4) 0.0182(14) Uani d . . . 1 . .
C C45 0.6419(5) 0.3305(6) 0.4364(4) 0.0233(15) Uani d . . . 1 . .
H H45 0.698 0.3306 0.4238 0.028 Uiso calc U . R 1 . .
C C50 0.5628(5) 0.3324(6) 0.5362(4) 0.0172(14) Uani d . . . 1 . .
C C47 0.7223(5) 0.3347(6) 0.6573(4) 0.0205(15) Uani d . . . 1 . .
H H47 0.7779 0.3366 0.7005 0.025 Uiso calc U . R 1 . .
C C41 0.3088(5) 0.3276(6) 0.3593(4) 0.0248(16) Uani d . . . 1 . .
H H41 0.2496 0.3262 0.3207 0.03 Uiso calc U . R 1 . .
C C43 0.4749(5) 0.3301(5) 0.3944(4) 0.0196(15) Uani d . . . 1 . .
C C42 0.3869(5) 0.3274(6) 0.3362(4) 0.0232(15) Uani d . . . 1 . .
H H42 0.382 0.3254 0.2815 0.028 Uiso calc U . R 1 . .
C C53 0.5469(4) 0.3351(5) 0.7745(4) 0.0135(13) Uani d . . . 1 . .
C C55 0.7141(5) 0.3636(6) 0.8171(4) 0.0181(15) Uani d . . . 1 . .
H H55 0.7704 0.3693 0.8051 0.022 Uiso calc U . R 1 . .
C C54 0.5492(5) 0.3457(5) 0.8544(4) 0.0176(15) Uani d . . . 1 . .
C C58 0.6347(6) 0.3811(6) 0.9967(4) 0.0236(16) Uani d . . . 1 . .
H H58 0.5795 0.3785 1.0107 0.028 Uiso calc U . R 1 . .
C C56 0.7151(5) 0.3744(6) 0.8967(4) 0.0202(15) Uani d . . . 1 . .
C C57 0.6308(5) 0.3659(6) 0.9139(4) 0.0228(16) Uani d . . . 1 . .
C C52 0.6317(4) 0.3447(5) 0.7547(4) 0.0164(14) Uani d . . . 1 . .
C C59 0.7988(5) 0.3918(8) 0.9573(5) 0.034(2) Uani d . . . 1 . .
H H59 0.8547 0.3945 0.9445 0.041 Uiso calc U . R 1 . .
C C60 0.8005(6) 0.4049(8) 1.0346(5) 0.038(2) Uani d . . . 1 . .
H H60 0.857 0.4178 1.0751 0.045 Uiso calc U . R 1 . .
C C61 0.7155(6) 0.3987(7) 1.0533(5) 0.0304(19) Uani d . . . 1 . .
H H61 0.7164 0.4072 1.1067 0.037 Uiso calc U . R 1 . .
C C70 0.4065(5) 0.2558(6) 0.8640(4) 0.0217(16) Uani d . . . 1 . .
C C71 0.4569(5) 0.3445(6) 0.8677(4) 0.0197(15) Uani d . . . 1 . .
C C65 0.4642(6) 0.5374(6) 0.8823(5) 0.0312(19) Uani d . . . 1 . .
H H65 0.5277 0.5375 0.8862 0.037 Uiso calc U . R 1 . .
C C67 0.3181(6) 0.4466(9) 0.8678(5) 0.038(2) Uani d . . . 1 . .
C C66 0.4144(5) 0.4408(6) 0.8740(4) 0.0239(17) Uani d . . . 1 . .
C C69 0.3136(5) 0.2617(7) 0.8626(5) 0.0305(19) Uani d . . . 1 . .
H H69 0.2801 0.1998 0.8612 0.037 Uiso calc U . R 1 . .
C C62 0.4199(7) 0.6284(7) 0.8846(5) 0.035(2) Uani d . . . 1 . .
H H62 0.4535 0.6907 0.8896 0.042 Uiso calc U . R 1 . .
C C68 0.2711(5) 0.3510(8) 0.8632(5) 0.036(2) Uani d . . . 1 . .
H H68 0.208 0.3509 0.8605 0.043 Uiso calc U . R 1 . .
C C63 0.3256(7) 0.6322(9) 0.8796(5) 0.047(3) Uani d . . . 1 . .
H H63 0.296 0.6958 0.8817 0.056 Uiso calc U . R 1 . .
C C64 0.2774(7) 0.5401(8) 0.8716(5) 0.042(2) Uani d . . . 1 . .
H H64 0.2142 0.5417 0.8687 0.051 Uiso calc U . R 1 . .
C C73 0.4457(5) 0.1518(6) 0.8602(5) 0.0228(16) Uani d . . . 1 . .
C C74 0.3922(5) 0.0803(7) 0.8054(5) 0.0302(19) Uani d . . . 1 . .
H H74 0.3358 0.1014 0.7678 0.036 Uiso calc U . R 1 . .
C C77 0.5598(6) 0.0205(7) 0.9109(5) 0.0308(19) Uani d . . . 1 . .
H H77 0.6185 0.0016 0.9457 0.037 Uiso calc U . R 1 . .
C C72 0.5294(5) 0.1217(6) 0.9129(5) 0.0261(17) Uani d . . . 1 . .
H H72 0.566 0.1692 0.9501 0.031 Uiso calc U . R 1 . .
C C75 0.4216(6) -0.0214(7) 0.8060(5) 0.0304(19) Uani d . . . 1 . .
H H75 0.3846 -0.0701 0.7703 0.037 Uiso calc U . R 1 . .
C C76 0.5088(7) -0.0513(7) 0.8614(5) 0.036(2) Uani d . . . 1 . .
H H76 0.5301 -0.1201 0.8631 0.044 Uiso calc U . R 1 . .
C C78 0.8817(5) 0.1071(6) 0.4960(5) 0.0229(16) Uani d . . . 1 . .
C C79 0.2539(5) 0.2789(6) 0.6163(4) 0.0220(16) Uani d . . . 1 . .
O O23 0.8300(3) 0.0354(4) 0.6629(3) 0.0216(12) Uani d . . . 1 . .
O O21 0.3039(3) 0.3534(4) 0.6077(3) 0.0229(12) Uani d . . . 1 . .
O O4 0.8464(3) 0.0256(4) 0.5151(3) 0.0208(11) Uani d . . . 1 . .
O O22 0.4664(3) 0.3156(4) 0.7228(3) 0.0175(10) Uani d . . . 1 . .
N N4 0.5581(4) 0.3332(5) 0.6113(3) 0.0135(11) Uani d . . . 1 . .
N N3 0.3986(4) 0.3303(5) 0.4955(3) 0.0158(12) Uani d . . . 1 . .
C C80 0.9733(6) 0.4290(7) 0.7659(8) 0.045(3) Uani d . . . 1 . .
H H80 0.96 0.5001 0.7669 0.055 Uiso calc U . R 1 . .
O O10 0.2784(4) 0.1869(4) 0.6216(4) 0.0365(14) Uani d . . . 1 . .
O O9 0.8512(4) 0.1941(4) 0.5048(4) 0.0326(14) Uani d . . . 1 . .
C C85 0.1588(5) 0.3076(7) 0.6183(5) 0.031(2) Uani d . . . 1 . .
H H85A 0.1142 0.2561 0.5893 0.047 Uiso calc U . R 1 . .
H H85B 0.1418 0.3749 0.5936 0.047 Uiso calc U . R 1 . .
H H85C 0.1586 0.3103 0.6735 0.047 Uiso calc U . R 1 . .
C C86 0.9583(7) 0.0952(7) 0.4624(6) 0.039(2) Uani d . . . 1 . .
H H86A 0.9745 0.1624 0.4458 0.059 Uiso calc U . R 1 . .
H H86B 0.9394 0.0492 0.4166 0.059 Uiso calc U . R 1 . .
H H86C 1.012 0.0662 0.5027 0.059 Uiso calc U . R 1 . .
O O14 0.9219(4) 0.8462(5) 0.5892(3) 0.0308(13) Uani d . . . 1 . .
O O11 0.1940(4) 0.0289(5) 0.5237(4) 0.0356(14) Uani d . . . 1 . .
O O12 0.1488(4) 0.1379(5) 0.3821(4) 0.0408(15) Uani d . . . 1 . .
O O13 0.0934(5) 0.8683(5) 0.5502(4) 0.0455(17) Uani d . . . 1 . .
O O15 0.2081(6) 0.0834(8) 0.2521(5) 0.077(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O23 . 1.860(5) ?
Cu1 N2 . 1.967(6) ?
Cu1 O4 . 1.974(5) ?
Cu1 N1 . 1.979(6) ?
Cu2 O22 . 1.857(5) ?
Cu2 O21 . 1.914(5) ?
Cu2 N4 . 1.977(5) ?
Cu2 N3 . 1.995(6) ?
N2 C14 . 1.361(9) ?
N2 C10 . 1.374(8) ?
C9 C10 . 1.386(10) ?
C9 C11 . 1.405(10) ?
C9 C8 . 1.430(10) ?
C1 C2 . 1.377(11) ?
C1 C5 . 1.387(12) ?
C1 H1 . 0.95 ?
N1 C2 . 1.340(9) ?
N1 C4 . 1.367(9) ?
C12 C11 . 1.362(10) ?
C12 C14 . 1.391(10) ?
C12 H12 . 0.95 ?
C5 C6 . 1.402(11) ?
C5 H5 . 0.95 ?
C4 C10 . 1.413(10) ?
C4 C6 . 1.418(10) ?
C2 H2 . 0.95 ?
C6 C7 . 1.432(11) ?
C7 C8 . 1.343(11) ?
C7 H7 . 0.95 ?
C14 C24 . 1.471(9) ?
C11 H11 . 0.95 ?
C8 H8 . 0.95 ?
C23 O23 . 1.305(9) ?
C23 C22 . 1.405(9) ?
C23 C24 . 1.450(9) ?
C22 C19 . 1.404(10) ?
C22 C34 . 1.508(9) ?
C18 C17 . 1.356(11) ?
C18 C19 . 1.440(9) ?
C18 H18 . 0.95 ?
C24 C21 . 1.416(10) ?
C20 C21 . 1.392(10) ?
C20 C16 . 1.396(11) ?
C20 C19 . 1.435(10) ?
C15 C16 . 1.358(11) ?
C15 C17 . 1.416(11) ?
C15 H15 . 0.95 ?
C17 H17 . 0.95 ?
C21 H21 . 0.95 ?
C16 H16 . 0.95 ?
C26 C34 . 1.402(11) ?
C26 C25 . 1.423(11) ?
C26 C27 . 1.449(11) ?
C25 C29 . 1.408(11) ?
C25 C31 . 1.420(11) ?
C29 C30 . 1.353(12) ?
C29 H29 . 0.95 ?
C30 C28 . 1.405(12) ?
C30 H30 . 0.95 ?
C27 C28 . 1.355(11) ?
C27 H27 . 0.95 ?
C28 H28 . 0.95 ?
C34 C33 . 1.394(10) ?
C33 C32 . 1.428(10) ?
C33 C37 . 1.473(11) ?
C31 C32 . 1.363(12) ?
C31 H31 . 0.95 ?
C32 H32 . 0.95 ?
C37 C38 . 1.387(13) ?
C37 C36 . 1.413(13) ?
C36 C35 . 1.357(13) ?
C36 H36 . 0.95 ?
C38 C39 . 1.378(13) ?
C38 H38 . 0.95 ?
C39 C80 . 1.388(16) ?
C39 H39 . 0.95 ?
C35 C80 . 1.395(18) ?
C35 H35 . 0.95 ?
C44 C45 . 1.363(11) ?
C44 C43 . 1.432(10) ?
C44 H44 . 0.95 ?
C40 N3 . 1.318(9) ?
C40 C41 . 1.406(10) ?
C40 H40 . 0.95 ?
C49 N4 . 1.345(9) ?
C49 C47 . 1.430(9) ?
C49 C52 . 1.473(10) ?
C48 C47 . 1.351(10) ?
C48 C46 . 1.422(10) ?
C48 H48 . 0.95 ?
C51 N3 . 1.381(9) ?
C51 C43 . 1.384(10) ?
C51 C50 . 1.429(10) ?
C46 C50 . 1.396(10) ?
C46 C45 . 1.414(10) ?
C45 H45 . 0.95 ?
C50 N4 . 1.357(9) ?
C47 H47 . 0.95 ?
C41 C42 . 1.375(11) ?
C41 H41 . 0.95 ?
C43 C42 . 1.418(10) ?
C42 H42 . 0.95 ?
C53 O22 . 1.309(8) ?
C53 C54 . 1.414(9) ?
C53 C52 . 1.448(9) ?
C55 C56 . 1.415(10) ?
C55 C52 . 1.415(10) ?
C55 H55 . 0.95 ?
C54 C57 . 1.386(10) ?
C54 C71 . 1.500(9) ?
C58 C61 . 1.347(11) ?
C58 C57 . 1.465(10) ?
C58 H58 . 0.95 ?
C56 C59 . 1.409(10) ?
C56 C57 . 1.415(10) ?
C59 C60 . 1.375(12) ?
C59 H59 . 0.95 ?
C60 C61 . 1.437(12) ?
C60 H60 . 0.95 ?
C61 H61 . 0.95 ?
C70 C71 . 1.379(11) ?
C70 C69 . 1.413(11) ?
C70 C73 . 1.492(12) ?
C71 C66 . 1.433(11) ?
C65 C62 . 1.372(12) ?
C65 C66 . 1.455(12) ?
C65 H65 . 0.95 ?
C67 C64 . 1.378(14) ?
C67 C68 . 1.428(15) ?
C67 C66 . 1.441(11) ?
C69 C68 . 1.334(13) ?
C69 H69 . 0.95 ?
C62 C63 . 1.415(14) ?
C62 H62 . 0.95 ?
C68 H68 . 0.95 ?
C63 C64 . 1.392(16) ?
C63 H63 . 0.95 ?
C64 H64 . 0.95 ?
C73 C72 . 1.385(11) ?
C73 C74 . 1.410(11) ?
C74 C75 . 1.399(13) ?
C74 H74 . 0.95 ?
C77 C76 . 1.352(13) ?
C77 C72 . 1.402(12) ?
C77 H77 . 0.95 ?
C72 H72 . 0.95 ?
C75 C76 . 1.442(13) ?
C75 H75 . 0.95 ?
C76 H76 . 0.95 ?
C78 O9 . 1.253(10) ?
C78 O4 . 1.283(9) ?
C78 C86 . 1.476(11) ?
C79 O10 . 1.251(10) ?
C79 O21 . 1.272(9) ?
C79 C85 . 1.511(11) ?
C80 H80 . 0.95 ?
C85 H85A . 0.98 ?
C85 H85B . 0.98 ?
C85 H85C . 0.98 ?
C86 H86A . 0.98 ?
C86 H86B . 0.98 ?
C86 H86C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O23 Cu1 N2 . . 91.9(2) ?
O23 Cu1 O4 . . 90.1(2) ?
N2 Cu1 O4 . . 172.5(2) ?
O23 Cu1 N1 . . 171.3(2) ?
N2 Cu1 N1 . . 83.8(2) ?
O4 Cu1 N1 . . 93.2(2) ?
O22 Cu2 O21 . . 92.6(2) ?
O22 Cu2 N4 . . 92.3(2) ?
O21 Cu2 N4 . . 168.0(2) ?
O22 Cu2 N3 . . 173.9(2) ?
O21 Cu2 N3 . . 92.2(2) ?
N4 Cu2 N3 . . 83.9(2) ?
C14 N2 C10 . . 119.0(6) ?
C14 N2 Cu1 . . 129.0(4) ?
C10 N2 Cu1 . . 111.6(4) ?
C10 C9 C11 . . 115.8(6) ?
C10 C9 C8 . . 118.8(6) ?
C11 C9 C8 . . 125.3(6) ?
C2 C1 C5 . . 118.5(7) ?
C2 C1 H1 . . 120.8 ?
C5 C1 H1 . . 120.8 ?
C2 N1 C4 . . 118.2(6) ?
C2 N1 Cu1 . . 130.4(5) ?
C4 N1 Cu1 . . 111.1(4) ?
C11 C12 C14 . . 121.9(7) ?
C11 C12 H12 . . 119.0 ?
C14 C12 H12 . . 119.0 ?
C1 C5 C6 . . 120.7(7) ?
C1 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
N1 C4 C10 . . 116.9(6) ?
N1 C4 C6 . . 122.3(6) ?
C10 C4 C6 . . 120.8(6) ?
N1 C2 C1 . . 123.6(7) ?
N1 C2 H2 . . 118.2 ?
C1 C2 H2 . . 118.2 ?
C5 C6 C4 . . 116.7(6) ?
C5 C6 C7 . . 125.6(7) ?
C4 C6 C7 . . 117.7(6) ?
C8 C7 C6 . . 120.8(7) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
N2 C10 C9 . . 124.0(6) ?
N2 C10 C4 . . 116.0(6) ?
C9 C10 C4 . . 120.0(6) ?
N2 C14 C12 . . 118.9(6) ?
N2 C14 C24 . . 118.8(6) ?
C12 C14 C24 . . 122.3(6) ?
C12 C11 C9 . . 120.4(6) ?
C12 C11 H11 . . 119.8 ?
C9 C11 H11 . . 119.8 ?
C7 C8 C9 . . 121.9(7) ?
C7 C8 H8 . . 119.1 ?
C9 C8 H8 . . 119.1 ?
O23 C23 C22 . . 117.4(6) ?
O23 C23 C24 . . 124.2(6) ?
C22 C23 C24 . . 118.4(6) ?
C19 C22 C23 . . 122.5(6) ?
C19 C22 C34 . . 121.9(6) ?
C23 C22 C34 . . 115.7(6) ?
C17 C18 C19 . . 120.3(7) ?
C17 C18 H18 . . 119.9 ?
C19 C18 H18 . . 119.9 ?
C21 C24 C23 . . 117.9(6) ?
C21 C24 C14 . . 118.6(6) ?
C23 C24 C14 . . 123.5(6) ?
C21 C20 C16 . . 122.1(7) ?
C21 C20 C19 . . 118.0(6) ?
C16 C20 C19 . . 119.9(6) ?
C22 C19 C20 . . 119.5(6) ?
C22 C19 C18 . . 122.9(6) ?
C20 C19 C18 . . 117.5(6) ?
C16 C15 C17 . . 120.2(7) ?
C16 C15 H15 . . 119.9 ?
C17 C15 H15 . . 119.9 ?
C18 C17 C15 . . 121.0(7) ?
C18 C17 H17 . . 119.5 ?
C15 C17 H17 . . 119.5 ?
C20 C21 C24 . . 123.6(6) ?
C20 C21 H21 . . 118.2 ?
C24 C21 H21 . . 118.2 ?
C15 C16 C20 . . 121.0(7) ?
C15 C16 H16 . . 119.5 ?
C20 C16 H16 . . 119.5 ?
C34 C26 C25 . . 120.8(6) ?
C34 C26 C27 . . 122.2(6) ?
C25 C26 C27 . . 117.0(7) ?
C29 C25 C31 . . 123.2(7) ?
C29 C25 C26 . . 119.5(7) ?
C31 C25 C26 . . 117.3(7) ?
C30 C29 C25 . . 122.0(7) ?
C30 C29 H29 . . 119.0 ?
C25 C29 H29 . . 119.0 ?
C29 C30 C28 . . 119.4(7) ?
C29 C30 H30 . . 120.3 ?
C28 C30 H30 . . 120.3 ?
C28 C27 C26 . . 120.7(7) ?
C28 C27 H27 . . 119.6 ?
C26 C27 H27 . . 119.6 ?
C27 C28 C30 . . 121.4(8) ?
C27 C28 H28 . . 119.3 ?
C30 C28 H28 . . 119.3 ?
C33 C34 C26 . . 121.0(6) ?
C33 C34 C22 . . 118.3(6) ?
C26 C34 C22 . . 120.5(6) ?
C34 C33 C32 . . 118.1(7) ?
C34 C33 C37 . . 122.9(6) ?
C32 C33 C37 . . 119.0(7) ?
C32 C31 C25 . . 121.5(7) ?
C32 C31 H31 . . 119.2 ?
C25 C31 H31 . . 119.2 ?
C31 C32 C33 . . 121.3(7) ?
C31 C32 H32 . . 119.4 ?
C33 C32 H32 . . 119.4 ?
C38 C37 C36 . . 118.9(8) ?
C38 C37 C33 . . 120.0(8) ?
C36 C37 C33 . . 121.1(8) ?
C35 C36 C37 . . 119.3(11) ?
C35 C36 H36 . . 120.4 ?
C37 C36 H36 . . 120.4 ?
C39 C38 C37 . . 120.2(10) ?
C39 C38 H38 . . 119.9 ?
C37 C38 H38 . . 119.9 ?
C38 C39 C80 . . 121.6(11) ?
C38 C39 H39 . . 119.2 ?
C80 C39 H39 . . 119.2 ?
C36 C35 C80 . . 122.8(11) ?
C36 C35 H35 . . 118.6 ?
C80 C35 H35 . . 118.6 ?
C45 C44 C43 . . 120.2(7) ?
C45 C44 H44 . . 119.9 ?
C43 C44 H44 . . 119.9 ?
N3 C40 C41 . . 121.8(7) ?
N3 C40 H40 . . 119.1 ?
C41 C40 H40 . . 119.1 ?
N4 C49 C47 . . 118.3(6) ?
N4 C49 C52 . . 120.5(6) ?
C47 C49 C52 . . 121.3(6) ?
C47 C48 C46 . . 120.3(6) ?
C47 C48 H48 . . 119.8 ?
C46 C48 H48 . . 119.8 ?
N3 C51 C43 . . 122.3(6) ?
N3 C51 C50 . . 116.0(6) ?
C43 C51 C50 . . 121.7(6) ?
C50 C46 C45 . . 119.9(7) ?
C50 C46 C48 . . 115.2(6) ?
C45 C46 C48 . . 124.9(6) ?
C44 C45 C46 . . 121.3(7) ?
C44 C45 H45 . . 119.3 ?
C46 C45 H45 . . 119.3 ?
N4 C50 C46 . . 124.5(6) ?
N4 C50 C51 . . 117.2(6) ?
C46 C50 C51 . . 118.3(6) ?
C48 C47 C49 . . 121.6(7) ?
C48 C47 H47 . . 119.2 ?
C49 C47 H47 . . 119.2 ?
C42 C41 C40 . . 119.4(7) ?
C42 C41 H41 . . 120.3 ?
C40 C41 H41 . . 120.3 ?
C51 C43 C42 . . 117.4(7) ?
C51 C43 C44 . . 118.5(7) ?
C42 C43 C44 . . 124.0(7) ?
C41 C42 C43 . . 119.7(7) ?
C41 C42 H42 . . 120.1 ?
C43 C42 H42 . . 120.1 ?
O22 C53 C54 . . 116.6(6) ?
O22 C53 C52 . . 124.2(6) ?
C54 C53 C52 . . 119.2(6) ?
C56 C55 C52 . . 122.0(6) ?
C56 C55 H55 . . 119.0 ?
C52 C55 H55 . . 119.0 ?
C57 C54 C53 . . 121.3(6) ?
C57 C54 C71 . . 123.3(6) ?
C53 C54 C71 . . 115.1(6) ?
C61 C58 C57 . . 120.9(7) ?
C61 C58 H58 . . 119.5 ?
C57 C58 H58 . . 119.5 ?
C59 C56 C55 . . 120.3(7) ?
C59 C56 C57 . . 121.1(7) ?
C55 C56 C57 . . 118.6(7) ?
C54 C57 C56 . . 120.8(7) ?
C54 C57 C58 . . 122.5(7) ?
C56 C57 C58 . . 116.7(7) ?
C55 C52 C53 . . 118.0(6) ?
C55 C52 C49 . . 118.8(6) ?
C53 C52 C49 . . 123.2(6) ?
C60 C59 C56 . . 120.9(7) ?
C60 C59 H59 . . 119.6 ?
C56 C59 H59 . . 119.6 ?
C59 C60 C61 . . 119.0(7) ?
C59 C60 H60 . . 120.5 ?
C61 C60 H60 . . 120.5 ?
C58 C61 C60 . . 121.3(8) ?
C58 C61 H61 . . 119.3 ?
C60 C61 H61 . . 119.3 ?
C71 C70 C69 . . 119.8(7) ?
C71 C70 C73 . . 122.5(6) ?
C69 C70 C73 . . 117.7(7) ?
C70 C71 C66 . . 118.7(6) ?
C70 C71 C54 . . 122.6(7) ?
C66 C71 C54 . . 118.2(7) ?
C62 C65 C66 . . 120.3(8) ?
C62 C65 H65 . . 119.9 ?
C66 C65 H65 . . 119.9 ?
C64 C67 C68 . . 123.3(8) ?
C64 C67 C66 . . 120.5(10) ?
C68 C67 C66 . . 116.1(8) ?
C71 C66 C67 . . 121.0(8) ?
C71 C66 C65 . . 122.1(7) ?
C67 C66 C65 . . 116.8(8) ?
C68 C69 C70 . . 122.3(8) ?
C68 C69 H69 . . 118.8 ?
C70 C69 H69 . . 118.8 ?
C65 C62 C63 . . 122.0(9) ?
C65 C62 H62 . . 119.0 ?
C63 C62 H62 . . 119.0 ?
C69 C68 C67 . . 121.7(7) ?
C69 C68 H68 . . 119.1 ?
C67 C68 H68 . . 119.1 ?
C64 C63 C62 . . 118.1(8) ?
C64 C63 H63 . . 120.9 ?
C62 C63 H63 . . 120.9 ?
C67 C64 C63 . . 122.4(9) ?
C67 C64 H64 . . 118.8 ?
C63 C64 H64 . . 118.8 ?
C72 C73 C74 . . 119.6(8) ?
C72 C73 C70 . . 121.7(7) ?
C74 C73 C70 . . 118.4(7) ?
C75 C74 C73 . . 120.3(8) ?
C75 C74 H74 . . 119.9 ?
C73 C74 H74 . . 119.9 ?
C76 C77 C72 . . 122.7(9) ?
C76 C77 H77 . . 118.6 ?
C72 C77 H77 . . 118.6 ?
C73 C72 C77 . . 119.4(8) ?
C73 C72 H72 . . 120.3 ?
C77 C72 H72 . . 120.3 ?
C74 C75 C76 . . 119.3(8) ?
C74 C75 H75 . . 120.4 ?
C76 C75 H75 . . 120.4 ?
C77 C76 C75 . . 118.6(8) ?
C77 C76 H76 . . 120.7 ?
C75 C76 H76 . . 120.7 ?
O9 C78 O4 . . 120.9(6) ?
O9 C78 C86 . . 121.1(7) ?
O4 C78 C86 . . 118.0(7) ?
O10 C79 O21 . . 124.4(7) ?
O10 C79 C85 . . 120.1(7) ?
O21 C79 C85 . . 115.5(7) ?
C23 O23 Cu1 . . 128.6(4) ?
C79 O21 Cu2 . . 119.5(5) ?
C78 O4 Cu1 . . 109.8(4) ?
C53 O22 Cu2 . . 129.1(4) ?
C49 N4 C50 . . 119.9(5) ?
C49 N4 Cu2 . . 128.1(4) ?
C50 N4 Cu2 . . 111.9(4) ?
C40 N3 C51 . . 119.4(6) ?
C40 N3 Cu2 . . 129.6(5) ?
C51 N3 Cu2 . . 111.0(4) ?
C39 C80 C35 . . 117.2(9) ?
C39 C80 H80 . . 121.4 ?
C35 C80 H80 . . 121.4 ?
C79 C85 H85A . . 109.5 ?
C79 C85 H85B . . 109.5 ?
H85A C85 H85B . . 109.5 ?
C79 C85 H85C . . 109.5 ?
H85A C85 H85C . . 109.5 ?
H85B C85 H85C . . 109.5 ?
C78 C86 H86A . . 109.5 ?
C78 C86 H86B . . 109.5 ?
H86A C86 H86B . . 109.5 ?
C78 C86 H86C . . 109.5 ?
H86A C86 H86C . . 109.5 ?
H86B C86 H86C . . 109.5 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
