# 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. 
# 
#######################################################################

data_tk_Cu2_Zw_Bipy
_database_code_depnum_ccdc_archive 'CCDC 1039320'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C120 H130 Cu2 N16 O4, 4(C H2 Cl2), 2(B F4)'
_chemical_formula_sum            'C124 H138 B2 Cl8 Cu2 F8 N16 O4'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            red

_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         2500.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.9140(8)
_cell_length_b                   14.2234(7)
_cell_length_c                   18.4642(8)
_cell_angle_alpha                104.264(3)
_cell_angle_beta                 92.349(3)
_cell_angle_gamma                105.810(2)
_cell_volume                     3141.3(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7131
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      26.022
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1302
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18166
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.1042
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.15
_diffrn_reflns_theta_max         26.00
_reflns_number_total             12262
_reflns_number_gt                7503
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  PLATON

_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)+(0.0967P)²+1.8801P] 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_number_reflns         12262
_refine_ls_number_parameters     757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1378
_refine_ls_R_factor_gt           0.0745
_refine_ls_wR_factor_ref         0.2020
_refine_ls_wR_factor_gt          0.1605
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.76054(5) 0.31539(4) 0.21886(3) 0.02886(17) Uani 1 1 d . . .
Cl3 Cl 0.49574(13) 0.37331(11) 0.41890(8) 0.0579(4) Uani 1 1 d . . .
Cl2 Cl 0.85486(17) 0.14278(14) 0.32262(9) 0.0823(5) Uani 1 1 d . . .
Cl4 Cl 0.26291(16) 0.31746(14) 0.38453(11) 0.0908(6) Uani 1 1 d . . .
Cl1 Cl 0.8427(2) -0.06730(17) 0.31012(14) 0.1206(9) Uani 1 1 d . . .
F1 F 0.2818(3) 0.5846(2) 0.40539(16) 0.0607(9) Uani 1 1 d . . .
F2 F 0.1924(3) 0.5359(2) 0.28650(16) 0.0606(9) Uani 1 1 d . . .
O1 O 0.6557(3) 0.2381(2) 0.42540(17) 0.0393(8) Uani 1 1 d . . .
F3 F 0.2731(3) 0.7010(2) 0.34471(16) 0.0620(9) Uani 1 1 d . . .
F4 F 0.3735(3) 0.5999(3) 0.30589(18) 0.0718(10) Uani 1 1 d . . .
O2 O 0.3910(3) -0.0762(2) 0.32827(17) 0.0405(8) Uani 1 1 d . . .
N7 N 0.7352(3) 0.3829(2) 0.13510(17) 0.0227(8) Uani 1 1 d . . .
N8 N 0.7962(3) 0.2107(2) 0.12455(17) 0.0226(8) Uani 1 1 d . . .
N6 N 0.8528(3) 0.3914(3) 0.31658(17) 0.0276(8) Uani 1 1 d . . .
N2 N 0.4927(4) -0.1609(3) 0.4065(2) 0.0317(9) Uani 1 1 d . . .
N3 N 0.6270(3) 0.2370(3) 0.25098(18) 0.0293(9) Uani 1 1 d . . .
N1 N 0.7574(3) 0.1609(3) 0.5087(2) 0.0352(10) Uani 1 1 d . . .
C31 C 0.7539(3) 0.2419(3) -0.1328(2) 0.0276(10) Uani 1 1 d . . .
C35 C 0.7843(3) 0.1914(3) -0.0169(2) 0.0242(9) Uani 1 1 d . . .
C26 C 0.7420(3) 0.3286(3) 0.0692(2) 0.0214(9) Uani 1 1 d . . .
C36 C 0.7544(3) 0.2570(3) -0.0547(2) 0.0242(9) Uani 1 1 d . . .
C1 C 0.5207(4) 0.0851(3) 0.3690(2) 0.0283(10) Uani 1 1 d . . .
C6 C 0.4738(4) -0.0188(3) 0.3675(2) 0.0301(10) Uani 1 1 d . . .
C37 C 0.8382(4) 0.1250(3) 0.1168(2) 0.0247(10) Uani 1 1 d . . .
C22 C 0.9690(4) 0.4779(3) 0.4617(2) 0.0261(10) Uani 1 1 d . . .
C29 C 0.7013(4) 0.3962(4) -0.1171(2) 0.0362(11) Uani 1 1 d . . .
H29 H 0.6832 0.4443 -0.1391 0.043 Uiso 1 1 calc R . .
C33 C 0.8185(4) 0.0969(3) -0.1352(2) 0.0295(10) Uani 1 1 d . . .
H33 H 0.8423 0.0427 -0.1632 0.035 Uiso 1 1 calc R . .
C27 C 0.7298(3) 0.3405(3) -0.0075(2) 0.0249(9) Uani 1 1 d . . .
C23 C 0.8569(4) 0.4459(3) 0.4508(2) 0.0329(11) Uani 1 1 d . . .
H23 H 0.8170 0.4526 0.4930 0.039 Uiso 1 1 calc R . .
N4 N 0.3308(4) 0.1473(3) 0.1580(2) 0.0475(11) Uani 1 1 d . . .
C8 C 0.3772(4) 0.1031(3) 0.2807(2) 0.0289(10) Uani 1 1 d . . .
C21 C 1.0200(4) 0.4658(4) 0.3973(2) 0.0378(12) Uani 1 1 d . . .
H21 H 1.0969 0.4869 0.4014 0.045 Uiso 1 1 calc R . .
C42 C 0.9511(4) 0.1439(3) 0.1218(2) 0.0285(10) Uani 1 1 d . . .
C49 C 0.7132(4) 0.4781(3) 0.1402(2) 0.0244(9) Uani 1 1 d . . .
C10 C 0.3527(4) 0.1302(3) 0.2134(3) 0.0343(11) Uani 1 1 d . . .
C30 C 0.7243(4) 0.3145(3) -0.1627(2) 0.0336(11) Uani 1 1 d . . .
H30 H 0.7202 0.3064 -0.2155 0.040 Uiso 1 1 calc R . .
C34 C 0.8164(4) 0.1110(3) -0.0565(2) 0.0267(10) Uani 1 1 d . . .
H34 H 0.8366 0.0661 -0.0321 0.032 Uiso 1 1 calc R . .
C25 C 0.7760(3) 0.2348(3) 0.0638(2) 0.0226(9) Uani 1 1 d . . .
C54 C 0.8014(4) 0.5644(3) 0.1466(2) 0.0311(10) Uani 1 1 d . . .
C7 C 0.4816(4) 0.1254(3) 0.3123(2) 0.0274(10) Uani 1 1 d . . .
C28 C 0.7036(4) 0.4113(3) -0.0384(2) 0.0306(10) Uani 1 1 d . . .
H28 H 0.6876 0.4686 -0.0077 0.037 Uiso 1 1 calc R . .
N5 N 0.2067(4) 0.0335(3) 0.3409(2) 0.0491(11) Uani 1 1 d . . .
C11 C 0.5630(4) 0.1904(3) 0.2800(2) 0.0267(10) Uani 1 1 d . . .
C39 C 0.8124(4) -0.0535(3) 0.0910(2) 0.0369(12) Uani 1 1 d . . .
H39 H 0.7665 -0.1209 0.0820 0.044 Uiso 1 1 calc R . .
C5 C 0.5380(4) -0.0631(3) 0.4149(2) 0.0303(10) Uani 1 1 d . . .
C32 C 0.7869(4) 0.1594(3) -0.1724(2) 0.0332(11) Uani 1 1 d . . .
H32 H 0.7875 0.1464 -0.2254 0.040 Uiso 1 1 calc R . .
C24 C 0.8028(4) 0.4044(3) 0.3792(2) 0.0336(11) Uani 1 1 d . . .
H24 H 0.7259 0.3837 0.3738 0.040 Uiso 1 1 calc R . .
C50 C 0.6066(4) 0.4819(3) 0.1401(2) 0.0298(10) Uani 1 1 d . . .
C38 C 0.7667(4) 0.0260(3) 0.1033(2) 0.0285(10) Uani 1 1 d . . .
C3 C 0.6707(4) 0.0973(3) 0.4660(2) 0.0295(10) Uani 1 1 d . . .
C41 C 0.9916(4) 0.0607(4) 0.1076(2) 0.0374(12) Uani 1 1 d . . .
H41 H 1.0676 0.0711 0.1088 0.045 Uiso 1 1 calc R . .
C4 C 0.6321(4) -0.0049(3) 0.4615(2) 0.0319(11) Uani 1 1 d . . .
H4 H 0.6698 -0.0350 0.4901 0.038 Uiso 1 1 calc R . .
C46 C 0.6436(4) 0.0049(3) 0.1026(3) 0.0357(11) Uani 1 1 d . . .
H46 H 0.6262 0.0702 0.1065 0.043 Uiso 1 1 calc R . .
C2 C 0.6157(4) 0.1465(3) 0.4185(2) 0.0292(10) Uani 1 1 d . . .
C52 C 0.6741(5) 0.6610(4) 0.1483(3) 0.0493(14) Uani 1 1 d . . .
H52 H 0.6599 0.7236 0.1499 0.059 Uiso 1 1 calc R . .
C9 C 0.2845(4) 0.0604(3) 0.3150(3) 0.0333(11) Uani 1 1 d . . .
C40 C 0.9222(4) -0.0373(4) 0.0916(3) 0.0404(12) Uani 1 1 d . . .
H40 H 0.9509 -0.0934 0.0811 0.048 Uiso 1 1 calc R . .
C12 C 0.8297(4) 0.1363(4) 0.5600(3) 0.0505(14) Uani 1 1 d . . .
H12A H 0.8434 0.0714 0.5350 0.061 Uiso 1 1 calc R . .
H12B H 0.7945 0.1279 0.6056 0.061 Uiso 1 1 calc R . .
C43 C 1.0273(4) 0.2514(3) 0.1412(2) 0.0351(11) Uani 1 1 d . . .
H43 H 0.9831 0.2992 0.1570 0.042 Uiso 1 1 calc R . .
C51 C 0.5894(4) 0.5757(3) 0.1439(3) 0.0412(12) Uani 1 1 d . . .
H51 H 0.5176 0.5808 0.1434 0.049 Uiso 1 1 calc R . .
C53 C 0.7790(4) 0.6562(3) 0.1505(3) 0.0412(12) Uani 1 1 d . . .
H53 H 0.8369 0.7159 0.1547 0.049 Uiso 1 1 calc R . .
C16 C 0.5398(4) -0.2272(3) 0.4365(3) 0.0368(11) Uani 1 1 d . . .
H16A H 0.4819 -0.2866 0.4415 0.044 Uiso 1 1 calc R . .
H16B H 0.5798 -0.1904 0.4869 0.044 Uiso 1 1 calc R . .
C55 C 0.9173(4) 0.5612(4) 0.1505(3) 0.0448(13) Uani 1 1 d . . .
H55 H 0.9164 0.4900 0.1482 0.054 Uiso 1 1 calc R . .
C58 C 0.5117(4) 0.3901(3) 0.1372(3) 0.0348(11) Uani 1 1 d . . .
H58 H 0.5410 0.3312 0.1347 0.042 Uiso 1 1 calc R . .
C59 C 0.4301(4) 0.3627(4) 0.0679(3) 0.0531(14) Uani 1 1 d . . .
H59A H 0.3982 0.4183 0.0698 0.080 Uiso 1 1 calc R . .
H59B H 0.3727 0.3007 0.0669 0.080 Uiso 1 1 calc R . .
H59C H 0.4668 0.3515 0.0225 0.080 Uiso 1 1 calc R . .
C17 C 0.6181(5) -0.2627(4) 0.3818(3) 0.0507(14) Uani 1 1 d . . .
H17A H 0.5788 -0.2921 0.3305 0.061 Uiso 1 1 calc R . .
H17B H 0.6785 -0.2029 0.3806 0.061 Uiso 1 1 calc R . .
C20 C 0.9612(4) 0.4236(4) 0.3269(2) 0.0352(11) Uani 1 1 d . . .
H20 H 0.9995 0.4171 0.2840 0.042 Uiso 1 1 calc R . .
C48 C 0.6059(5) -0.0330(4) 0.1701(3) 0.0546(15) Uani 1 1 d . . .
H48A H 0.6238 -0.0963 0.1680 0.082 Uiso 1 1 calc R . .
H48B H 0.5274 -0.0454 0.1692 0.082 Uiso 1 1 calc R . .
H48C H 0.6424 0.0181 0.2166 0.082 Uiso 1 1 calc R . .
B1 B 0.2782(5) 0.6033(4) 0.3352(3) 0.0339(13) Uani 1 1 d . . .
C13 C 0.9359(5) 0.2194(5) 0.5822(3) 0.0592(16) Uani 1 1 d . . .
H13A H 0.9201 0.2845 0.6033 0.071 Uiso 1 1 calc R . .
H13B H 0.9776 0.2062 0.6228 0.071 Uiso 1 1 calc R . .
C45 C 1.0819(5) 0.2754(5) 0.0743(3) 0.0677(19) Uani 1 1 d . . .
H45A H 1.1263 0.2299 0.0579 0.102 Uiso 1 1 calc R . .
H45B H 1.1280 0.3458 0.0886 0.102 Uiso 1 1 calc R . .
H45C H 1.0266 0.2661 0.0331 0.102 Uiso 1 1 calc R . .
C44 C 1.1117(5) 0.2689(4) 0.2074(3) 0.0548(15) Uani 1 1 d . . .
H44A H 1.0749 0.2542 0.2505 0.082 Uiso 1 1 calc R . .
H44B H 1.1569 0.3397 0.2212 0.082 Uiso 1 1 calc R . .
H44C H 1.1573 0.2240 0.1930 0.082 Uiso 1 1 calc R . .
C14 C 1.0058(5) 0.2315(5) 0.5204(3) 0.0601(16) Uani 1 1 d . . .
H14A H 1.0652 0.2957 0.5385 0.072 Uiso 1 1 calc R . .
H14B H 0.9618 0.2373 0.4774 0.072 Uiso 1 1 calc R . .
C47 C 0.5837(5) -0.0703(5) 0.0296(3) 0.0674(17) Uani 1 1 d . . .
H47A H 0.6077 -0.0438 -0.0130 0.101 Uiso 1 1 calc R . .
H47B H 0.5056 -0.0804 0.0301 0.101 Uiso 1 1 calc R . .
H47C H 0.5992 -0.1352 0.0247 0.101 Uiso 1 1 calc R . .
C19 C 0.7394(5) -0.3706(5) 0.3468(3) 0.0651(17) Uani 1 1 d . . .
H19A H 0.6971 -0.4101 0.2983 0.098 Uiso 1 1 calc R . .
H19B H 0.7776 -0.4120 0.3657 0.098 Uiso 1 1 calc R . .
H19C H 0.7921 -0.3099 0.3403 0.098 Uiso 1 1 calc R . .
C18 C 0.6639(5) -0.3392(4) 0.4026(3) 0.0618(16) Uani 1 1 d . . .
H18A H 0.6041 -0.3996 0.4035 0.074 Uiso 1 1 calc R . .
H18B H 0.7042 -0.3103 0.4536 0.074 Uiso 1 1 calc R . .
C56 C 0.9723(5) 0.5891(5) 0.0836(3) 0.073(2) Uani 1 1 d . . .
H56A H 0.9257 0.5497 0.0367 0.109 Uiso 1 1 calc R . .
H56B H 1.0419 0.5740 0.0826 0.109 Uiso 1 1 calc R . .
H56C H 0.9845 0.6617 0.0886 0.109 Uiso 1 1 calc R . .
C57 C 0.9826(5) 0.6294(5) 0.2243(3) 0.0561(15) Uani 1 1 d . . .
H57A H 0.9917 0.7005 0.2256 0.084 Uiso 1 1 calc R . .
H57B H 1.0540 0.6181 0.2282 0.084 Uiso 1 1 calc R . .
H57C H 0.9443 0.6134 0.2664 0.084 Uiso 1 1 calc R . .
C62 C 0.3823(5) 0.4162(4) 0.4047(3) 0.0579(15) Uani 1 1 d . . .
H62A H 0.3783 0.4681 0.4506 0.069 Uiso 1 1 calc R . .
H62B H 0.3912 0.4484 0.3626 0.069 Uiso 1 1 calc R . .
C60 C 0.4577(5) 0.4075(4) 0.2095(3) 0.0531(15) Uani 1 1 d . . .
H60A H 0.5109 0.4204 0.2529 0.080 Uiso 1 1 calc R . .
H60B H 0.3976 0.3472 0.2077 0.080 Uiso 1 1 calc R . .
H60C H 0.4300 0.4662 0.2143 0.080 Uiso 1 1 calc R . .
C15 C 1.0548(6) 0.1455(5) 0.4929(4) 0.077(2) Uani 1 1 d . . .
H15A H 1.0916 0.1338 0.5359 0.116 Uiso 1 1 calc R . .
H15B H 1.1072 0.1633 0.4580 0.116 Uiso 1 1 calc R . .
H15C H 0.9973 0.0837 0.4670 0.116 Uiso 1 1 calc R . .
C61 C 0.9173(6) 0.0467(5) 0.2942(3) 0.0676(18) Uani 1 1 d . . .
H61A H 0.9254 0.0359 0.2400 0.081 Uiso 1 1 calc R . .
H61B H 0.9906 0.0685 0.3222 0.081 Uiso 1 1 calc R . .
H1N H 0.764(4) 0.221(4) 0.508(3) 0.047(16) Uiso 1 1 d . . .
H2N H 0.436(5) -0.182(4) 0.381(3) 0.051(18) 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 N3 1.983(4) . ?
Cu1 N6 2.001(3) . ?
Cu1 N7 2.069(3) . ?
Cu1 N8 2.151(3) . ?
Cl3 C62 1.766(6) . ?
Cl2 C61 1.753(7) . ?
Cl4 C62 1.733(6) . ?
Cl1 C61 1.746(6) . ?
F1 B1 1.387(6) . ?
F2 B1 1.368(6) . ?
O1 C2 1.237(5) . ?
F3 B1 1.376(6) . ?
F4 B1 1.374(6) . ?
O2 C6 1.227(5) . ?
N7 C26 1.292(5) . ?
N7 C49 1.439(5) . ?
N8 C25 1.289(5) . ?
N8 C37 1.441(5) . ?
N6 C20 1.339(6) . ?
N6 C24 1.345(5) . ?
N2 C5 1.320(6) . ?
N2 C16 1.454(6) . ?
N3 C11 1.149(5) . ?
N1 C3 1.310(6) . ?
N1 C12 1.470(6) . ?
C31 C32 1.404(6) . ?
C31 C36 1.405(5) . ?
C31 C30 1.412(6) . ?
C35 C34 1.374(6) . ?
C35 C36 1.415(6) . ?
C35 C25 1.486(5) . ?
C26 C27 1.473(5) . ?
C26 C25 1.496(6) . ?
C36 C27 1.411(6) . ?
C1 C2 1.426(6) . ?
C1 C6 1.429(6) . ?
C1 C7 1.446(6) . ?
C6 C5 1.533(6) . ?
C37 C42 1.404(6) . ?
C37 C38 1.414(6) . ?
C22 C21 1.379(6) . ?
C22 C23 1.384(6) . ?
C22 C22 1.493(8) 2_766 ?
C29 C30 1.369(6) . ?
C29 C28 1.414(6) . ?
C33 C32 1.379(6) . ?
C33 C34 1.419(5) . ?
C27 C28 1.382(6) . ?
C23 C24 1.378(6) . ?
N4 C10 1.151(6) . ?
C8 C7 1.367(6) . ?
C8 C9 1.435(6) . ?
C8 C10 1.436(6) . ?
C21 C20 1.383(6) . ?
C42 C41 1.393(6) . ?
C42 C43 1.521(6) . ?
C49 C50 1.392(6) . ?
C49 C54 1.405(6) . ?
C54 C53 1.398(6) . ?
C54 C55 1.510(7) . ?
C7 C11 1.452(6) . ?
N5 C9 1.143(6) . ?
C39 C40 1.372(7) . ?
C39 C38 1.387(6) . ?
C5 C4 1.385(6) . ?
C50 C51 1.397(6) . ?
C50 C58 1.516(6) . ?
C38 C46 1.534(7) . ?
C3 C4 1.382(6) . ?
C3 C2 1.512(6) . ?
C41 C40 1.388(7) . ?
C46 C47 1.520(7) . ?
C46 C48 1.524(7) . ?
C52 C53 1.375(7) . ?
C52 C51 1.376(7) . ?
C12 C13 1.510(7) . ?
C43 C45 1.512(7) . ?
C43 C44 1.528(7) . ?
C16 C17 1.552(7) . ?
C55 C57 1.522(7) . ?
C55 C56 1.533(7) . ?
C58 C59 1.524(7) . ?
C58 C60 1.528(7) . ?
C17 C18 1.490(7) . ?
C13 C14 1.498(8) . ?
C14 C15 1.516(9) . ?
C19 C18 1.518(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
N3 Cu1 N6 102.87(14) . . ?
N3 Cu1 N7 115.06(14) . . ?
N6 Cu1 N7 123.27(13) . . ?
N3 Cu1 N8 105.25(14) . . ?
N6 Cu1 N8 128.50(14) . . ?
N7 Cu1 N8 80.85(12) . . ?
C26 N7 C49 117.8(3) . . ?
C26 N7 Cu1 112.0(3) . . ?
C49 N7 Cu1 130.2(2) . . ?
C25 N8 C37 116.8(3) . . ?
C25 N8 Cu1 109.2(3) . . ?
C37 N8 Cu1 134.0(2) . . ?
C20 N6 C24 116.0(4) . . ?
C20 N6 Cu1 126.1(3) . . ?
C24 N6 Cu1 117.7(3) . . ?
C5 N2 C16 125.8(4) . . ?
C11 N3 Cu1 167.0(3) . . ?
C3 N1 C12 126.1(4) . . ?
C32 C31 C36 117.0(4) . . ?
C32 C31 C30 126.9(4) . . ?
C36 C31 C30 116.1(4) . . ?
C34 C35 C36 119.9(3) . . ?
C34 C35 C25 135.0(4) . . ?
C36 C35 C25 105.0(3) . . ?
N7 C26 C27 133.9(4) . . ?
N7 C26 C25 118.3(3) . . ?
C27 C26 C25 107.6(3) . . ?
C31 C36 C27 122.9(4) . . ?
C31 C36 C35 122.2(4) . . ?
C27 C36 C35 114.8(3) . . ?
C2 C1 C6 121.3(4) . . ?
C2 C1 C7 118.4(4) . . ?
C6 C1 C7 119.7(4) . . ?
O2 C6 C1 125.7(4) . . ?
O2 C6 C5 117.8(4) . . ?
C1 C6 C5 116.4(4) . . ?
C42 C37 C38 122.1(4) . . ?
C42 C37 N8 117.6(4) . . ?
C38 C37 N8 120.3(4) . . ?
C21 C22 C23 115.7(4) . . ?
C21 C22 C22 122.0(5) . 2_766 ?
C23 C22 C22 122.2(5) . 2_766 ?
C30 C29 C28 122.1(4) . . ?
C32 C33 C34 122.2(4) . . ?
C28 C27 C36 119.4(4) . . ?
C28 C27 C26 135.2(4) . . ?
C36 C27 C26 105.4(3) . . ?
C24 C23 C22 120.4(4) . . ?
C7 C8 C9 123.4(4) . . ?
C7 C8 C10 121.4(4) . . ?
C9 C8 C10 114.9(4) . . ?
C22 C21 C20 121.2(4) . . ?
C41 C42 C37 117.7(4) . . ?
C41 C42 C43 120.7(4) . . ?
C37 C42 C43 121.5(4) . . ?
C50 C49 C54 122.5(4) . . ?
C50 C49 N7 119.4(4) . . ?
C54 C49 N7 118.1(4) . . ?
N4 C10 C8 176.8(5) . . ?
C29 C30 C31 121.3(4) . . ?
C35 C34 C33 118.0(4) . . ?
N8 C25 C35 133.6(4) . . ?
N8 C25 C26 119.1(3) . . ?
C35 C25 C26 107.1(3) . . ?
C53 C54 C49 117.7(4) . . ?
C53 C54 C55 119.8(4) . . ?
C49 C54 C55 122.5(4) . . ?
C8 C7 C1 127.6(4) . . ?
C8 C7 C11 115.5(4) . . ?
C1 C7 C11 116.7(4) . . ?
C27 C28 C29 118.2(4) . . ?
N3 C11 C7 176.0(4) . . ?
C40 C39 C38 121.8(4) . . ?
N2 C5 C4 125.0(4) . . ?
N2 C5 C6 112.4(4) . . ?
C4 C5 C6 122.6(4) . . ?
C33 C32 C31 120.6(4) . . ?
N6 C24 C23 123.7(4) . . ?
C49 C50 C51 117.1(4) . . ?
C49 C50 C58 122.7(4) . . ?
C51 C50 C58 120.2(4) . . ?
C39 C38 C37 117.1(4) . . ?
C39 C38 C46 120.3(4) . . ?
C37 C38 C46 122.6(4) . . ?
N1 C3 C4 125.5(4) . . ?
N1 C3 C2 112.8(4) . . ?
C4 C3 C2 121.7(4) . . ?
C40 C41 C42 120.7(5) . . ?
C3 C4 C5 119.4(4) . . ?
C47 C46 C48 110.7(4) . . ?
C47 C46 C38 111.4(4) . . ?
C48 C46 C38 110.4(4) . . ?
O1 C2 C1 123.9(4) . . ?
O1 C2 C3 117.7(4) . . ?
C1 C2 C3 118.4(4) . . ?
C53 C52 C51 120.4(4) . . ?
N5 C9 C8 173.3(5) . . ?
C39 C40 C41 120.4(4) . . ?
N1 C12 C13 110.4(4) . . ?
C45 C43 C42 112.0(4) . . ?
C45 C43 C44 110.6(5) . . ?
C42 C43 C44 110.7(4) . . ?
C52 C51 C50 121.6(5) . . ?
C52 C53 C54 120.7(4) . . ?
N2 C16 C17 108.4(4) . . ?
C54 C55 C57 111.5(4) . . ?
C54 C55 C56 111.7(5) . . ?
C57 C55 C56 110.4(4) . . ?
C50 C58 C59 112.4(4) . . ?
C50 C58 C60 110.0(4) . . ?
C59 C58 C60 111.3(4) . . ?
C18 C17 C16 113.6(4) . . ?
N6 C20 C21 122.9(4) . . ?
F2 B1 F4 109.9(4) . . ?
F2 B1 F3 110.6(4) . . ?
F4 B1 F3 106.3(4) . . ?
F2 B1 F1 112.4(4) . . ?
F4 B1 F1 109.1(4) . . ?
F3 B1 F1 108.2(4) . . ?
C14 C13 C12 115.7(5) . . ?
C13 C14 C15 114.5(5) . . ?
C17 C18 C19 110.7(5) . . ?
Cl4 C62 Cl3 111.5(3) . . ?
Cl1 C61 Cl2 111.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.121
####################################################################### 
# 
# 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_pbvr100430
_database_code_depnum_ccdc_archive 'CCDC 1039321'
_audit_update_record             
;
2015-01-19 deposited with the CCDC.
2015-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C74 H82 Cu N12 O4, B F4, C H2 Cl2'
_chemical_formula_sum            'C75 H84 B Cl2 Cu F4 N12 O4'
_chemical_formula_weight         1438.79

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   14.8235(5)
_cell_length_b                   17.2794(7)
_cell_length_c                   17.8129(6)
_cell_angle_alpha                92.405(2)
_cell_angle_beta                 109.546(2)
_cell_angle_gamma                108.388(2)
_cell_volume                     4024.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    10680
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             1508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.399
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27157
_diffrn_reflns_av_unetI/netI     0.1225
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.230
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             18316
_reflns_number_gt                9832
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.1502P)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_number_reflns         18316
_refine_ls_number_parameters     886
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1660
_refine_ls_R_factor_gt           0.0987
_refine_ls_wR_factor_ref         0.2800
_refine_ls_wR_factor_gt          0.2511
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1737(3) 0.6835(3) 0.8391(2) 0.0268(9) Uani 1 1 d . . . . .
C2 C 0.0635(3) 0.6564(3) 0.8005(3) 0.0301(10) Uani 1 1 d . . . . .
C3 C 0.0072(3) 0.6895(3) 0.8364(3) 0.0313(10) Uani 1 1 d . . . . .
C4 C 0.0654(3) 0.7610(3) 0.9058(3) 0.0300(10) Uani 1 1 d . . . . .
C5 C 0.1715(3) 0.7912(3) 0.9400(3) 0.0299(9) Uani 1 1 d . . . . .
H5 H 0.2062 0.8353 0.9845 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2262(3) 0.7560(2) 0.9083(2) 0.0259(9) Uani 1 1 d . . . . .
C7 C 0.0095(3) 0.5923(3) 0.7318(3) 0.0295(9) Uani 1 1 d . . . . .
C8 C -0.0924(4) 0.5378(3) 0.7204(3) 0.0417(12) Uani 1 1 d . . . . .
C9 C 0.0428(3) 0.5764(3) 0.6713(3) 0.0307(10) Uani 1 1 d . . . . .
C10 C -0.0194(4) 0.5064(3) 0.6063(3) 0.0386(11) Uani 1 1 d . . . . .
C11 C 0.1348(3) 0.6284(3) 0.6632(3) 0.0312(10) Uani 1 1 d . . . . .
C12 C 0.3925(3) 0.8475(3) 1.0040(3) 0.0329(10) Uani 1 1 d . . . . .
H12A H 0.3868 0.8280 1.0542 0.039 Uiso 1 1 calc R U . . .
H12B H 0.3692 0.8955 0.9975 0.039 Uiso 1 1 calc R U . . .
C13 C 0.5028(3) 0.8745(3) 1.0113(3) 0.0310(10) Uani 1 1 d . . . . .
H13A H 0.5092 0.8984 0.9630 0.037 Uiso 1 1 calc R U . . .
H13B H 0.5240 0.8255 1.0128 0.037 Uiso 1 1 calc R U . . .
C14 C 0.5740(4) 0.9380(3) 1.0865(3) 0.0451(12) Uani 1 1 d . . . . .
H14A H 0.5554 0.9883 1.0838 0.054 Uiso 1 1 calc R U . . .
H14B H 0.5655 0.9153 1.1349 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6847(4) 0.9607(4) 1.0946(3) 0.0578(15) Uani 1 1 d . . . . .
H15A H 0.7038 0.9113 1.0990 0.087 Uiso 1 1 calc R U . . .
H15B H 0.7285 1.0022 1.1431 0.087 Uiso 1 1 calc R U . . .
H15C H 0.6933 0.9833 1.0469 0.087 Uiso 1 1 calc R U . . .
C16 C 0.0392(4) 0.8627(3) 0.9909(3) 0.0464(13) Uani 1 1 d . . . . .
H16A H -0.0076 0.8940 0.9731 0.056 Uiso 1 1 calc R U . . .
H16B H 0.1081 0.8994 0.9960 0.056 Uiso 1 1 calc R U . . .
C17 C 0.0429(10) 0.8431(6) 1.0708(6) 0.137(2) Uani 1 1 d . . . . .
H17A H 0.0984 0.8204 1.0921 0.165 Uiso 1 1 calc R U . . .
H17B H 0.0628 0.8957 1.1069 0.165 Uiso 1 1 calc R U . . .
C18 C -0.0444(10) 0.7884(6) 1.0775(6) 0.137(2) Uani 1 1 d . . . . .
H18A H -0.0628 0.7339 1.0451 0.165 Uiso 1 1 calc R U . . .
H18B H -0.1016 0.8089 1.0552 0.165 Uiso 1 1 calc R U . . .
C19 C -0.0293(9) 0.7784(6) 1.1635(6) 0.137(2) Uani 1 1 d . . . . .
H19A H 0.0375 0.7732 1.1901 0.206 Uiso 1 1 calc R U . . .
H19B H -0.0833 0.7287 1.1650 0.206 Uiso 1 1 calc R U . . .
H19C H -0.0324 0.8269 1.1917 0.206 Uiso 1 1 calc R U . . .
C20 C 0.6254(3) 0.7517(3) 0.8707(3) 0.0278(9) Uani 1 1 d . . . . .
C21 C 0.6981(3) 0.7125(3) 0.8714(3) 0.0312(10) Uani 1 1 d . . . . .
C22 C 0.6649(3) 0.6187(3) 0.8670(3) 0.0287(9) Uani 1 1 d . . . . .
C23 C 0.5708(3) 0.5724(3) 0.8686(3) 0.0315(10) Uani 1 1 d . . . . .
H23 H 0.5530 0.5145 0.8681 0.038 Uiso 1 1 calc R U . . .
C24 C 0.5018(3) 0.6116(3) 0.8707(3) 0.0293(9) Uani 1 1 d . . . . .
C25 C 0.5264(3) 0.7036(3) 0.8695(2) 0.0258(9) Uani 1 1 d . . . . .
C26 C 0.6580(3) 0.8397(3) 0.8777(3) 0.0267(9) Uani 1 1 d . . . . .
C27 C 0.7636(4) 0.8889(3) 0.9220(3) 0.0403(12) Uani 1 1 d . . . . .
C28 C 0.5969(3) 0.8855(3) 0.8477(2) 0.0253(9) Uani 1 1 d . . . . .
C29 C 0.6378(3) 0.9737(3) 0.8643(2) 0.0271(9) Uani 1 1 d . . . . .
C30 C 0.4979(4) 0.8484(3) 0.7877(3) 0.0302(10) Uani 1 1 d . . . . .
C31 C 0.3739(4) 0.4876(3) 0.8831(4) 0.0544(14) Uani 1 1 d . . . . .
H31A H 0.4248 0.4770 0.9300 0.065 Uiso 1 1 calc R U . . .
H31B H 0.3641 0.4513 0.8343 0.065 Uiso 1 1 calc R U . . .
C32 C 0.2741(4) 0.4675(4) 0.8958(4) 0.0664(17) Uani 1 1 d . . . . .
H32A H 0.2636 0.4184 0.9229 0.080 Uiso 1 1 calc R U . . .
H32B H 0.2776 0.5145 0.9318 0.080 Uiso 1 1 calc R U . . .
C33 C 0.1899(6) 0.4516(4) 0.8225(4) 0.0740(19) Uani 1 1 d . . . . .
H33A H 0.1809 0.4003 0.7895 0.089 Uiso 1 1 calc R U . . .
H33B H 0.2044 0.4975 0.7919 0.089 Uiso 1 1 calc R U . . .
C34 C 0.0862(5) 0.4418(5) 0.8371(5) 0.095(2) Uani 1 1 d . . . . .
H34A H 0.0693 0.3943 0.8644 0.143 Uiso 1 1 calc R U . . .
H34B H 0.0307 0.4331 0.7850 0.143 Uiso 1 1 calc R U . . .
H34C H 0.0951 0.4921 0.8707 0.143 Uiso 1 1 calc R U . . .
C35 C 0.7252(4) 0.5021(3) 0.8545(4) 0.0469(13) Uani 1 1 d . . . . .
H35A H 0.7119 0.4808 0.7979 0.056 Uiso 1 1 calc R U . . .
H35B H 0.6663 0.4697 0.8682 0.056 Uiso 1 1 calc R U . . .
C36 C 0.8197(4) 0.4901(3) 0.9090(4) 0.0555(15) Uani 1 1 d . . . . .
H36A H 0.8321 0.5102 0.9657 0.067 Uiso 1 1 calc R U . . .
H36B H 0.8789 0.5236 0.8963 0.067 Uiso 1 1 calc R U . . .
C37 C 0.8121(5) 0.4009(4) 0.9008(4) 0.0739(19) Uani 1 1 d . . . . .
H37A H 0.7524 0.3677 0.9131 0.089 Uiso 1 1 calc R U . . .
H37B H 0.7994 0.3811 0.8439 0.089 Uiso 1 1 calc R U . . .
C38 C 0.9023(7) 0.3864(6) 0.9528(6) 0.107(3) Uani 1 1 d . . . . .
H38A H 0.9625 0.4211 0.9431 0.161 Uiso 1 1 calc R U . . .
H38B H 0.8938 0.3281 0.9411 0.161 Uiso 1 1 calc R U . . .
H38C H 0.9115 0.4003 1.0095 0.161 Uiso 1 1 calc R U . . .
C39 C 0.3686(3) 0.7266(3) 0.4984(3) 0.0289(9) Uani 1 1 d . . . . .
C40 C 0.3071(3) 0.7836(3) 0.4818(2) 0.0272(9) Uani 1 1 d . . . . .
C41 C 0.2974(3) 0.8032(3) 0.3993(3) 0.0296(9) Uani 1 1 d . . . . .
C42 C 0.2563(3) 0.8541(3) 0.3528(3) 0.0380(11) Uani 1 1 d . . . . .
H42 H 0.2232 0.8854 0.3713 0.046 Uiso 1 1 calc R U . . .
C43 C 0.2655(4) 0.8582(3) 0.2763(3) 0.0464(13) Uani 1 1 d . . . . .
H43 H 0.2371 0.8925 0.2429 0.056 Uiso 1 1 calc R U . . .
C44 C 0.3145(4) 0.8140(3) 0.2486(3) 0.0421(12) Uani 1 1 d . . . . .
H44 H 0.3184 0.8182 0.1967 0.051 Uiso 1 1 calc R U . . .
C45 C 0.3579(3) 0.7635(3) 0.2954(3) 0.0347(10) Uani 1 1 d . . . . .
C46 C 0.4111(4) 0.7150(3) 0.2758(3) 0.0409(12) Uani 1 1 d . . . . .
H46 H 0.4191 0.7148 0.2251 0.049 Uiso 1 1 calc R U . . .
C47 C 0.4506(4) 0.6689(3) 0.3285(3) 0.0420(12) Uani 1 1 d . . . . .
H47 H 0.4859 0.6376 0.3133 0.050 Uiso 1 1 calc R U . . .
C48 C 0.4416(3) 0.6654(3) 0.4047(3) 0.0357(10) Uani 1 1 d . . . . .
H48 H 0.4698 0.6324 0.4401 0.043 Uiso 1 1 calc R U . . .
C49 C 0.3911(3) 0.7112(3) 0.4260(3) 0.0302(9) Uani 1 1 d . . . . .
C50 C 0.3489(3) 0.7591(3) 0.3709(2) 0.0291(9) Uani 1 1 d . . . . .
C51 C 0.4617(3) 0.6618(3) 0.5930(3) 0.0346(10) Uani 1 1 d . . . . .
C52 C 0.5681(4) 0.7025(3) 0.6116(3) 0.0435(12) Uani 1 1 d . . . . .
C53 C 0.6323(4) 0.6580(4) 0.6418(3) 0.0587(16) Uani 1 1 d . . . . .
H53 H 0.7040 0.6845 0.6564 0.070 Uiso 1 1 calc R U . . .
C54 C 0.5950(5) 0.5771(5) 0.6509(4) 0.0669(18) Uani 1 1 d . . . . .
H54 H 0.6405 0.5481 0.6708 0.080 Uiso 1 1 calc R U . . .
C55 C 0.4919(5) 0.5380(4) 0.6315(4) 0.0615(17) Uani 1 1 d . . . . .
H55 H 0.4671 0.4820 0.6384 0.074 Uiso 1 1 calc R U . . .
C56 C 0.4219(4) 0.5792(3) 0.6014(3) 0.0408(12) Uani 1 1 d . . . . .
C57 C 0.3082(4) 0.5319(3) 0.5761(3) 0.0426(12) Uani 1 1 d . . . . .
H57 H 0.2725 0.5721 0.5586 0.051 Uiso 1 1 calc R U . . .
C58 C 0.2697(5) 0.4648(4) 0.5052(4) 0.0684(17) Uani 1 1 d . . . . .
H58A H 0.2818 0.4891 0.4592 0.103 Uiso 1 1 calc R U . . .
H58B H 0.1963 0.4358 0.4909 0.103 Uiso 1 1 calc R U . . .
H58C H 0.3058 0.4256 0.5192 0.103 Uiso 1 1 calc R U . . .
C59 C 0.2794(5) 0.4980(4) 0.6449(4) 0.0688(18) Uani 1 1 d . . . . .
H59A H 0.3141 0.4589 0.6646 0.103 Uiso 1 1 calc R U . . .
H59B H 0.2053 0.4694 0.6259 0.103 Uiso 1 1 calc R U . . .
H59C H 0.3002 0.5435 0.6888 0.103 Uiso 1 1 calc R U . . .
C60 C 0.6547(7) 0.8481(5) 0.6755(5) 0.1008(19) Uani 1 1 d . . . . .
H60A H 0.6018 0.8427 0.6983 0.151 Uiso 1 1 calc R U . . .
H60B H 0.6799 0.9048 0.6654 0.151 Uiso 1 1 calc R U . . .
H60C H 0.7114 0.8355 0.7137 0.151 Uiso 1 1 calc R U . . .
C61 C 0.6120(4) 0.7909(4) 0.6001(3) 0.0546(14) Uani 1 1 d . . . . .
H61 H 0.5549 0.8054 0.5622 0.066 Uiso 1 1 calc R U . . .
C62 C 0.6936(7) 0.8019(5) 0.5621(5) 0.1008(19) Uani 1 1 d . . . . .
H62A H 0.7071 0.8551 0.5426 0.151 Uiso 1 1 calc R U . . .
H62B H 0.6690 0.7570 0.5167 0.151 Uiso 1 1 calc R U . . .
H62C H 0.7568 0.8008 0.6027 0.151 Uiso 1 1 calc R U . . .
C63 C 0.2203(3) 0.8610(3) 0.5208(3) 0.0317(10) Uani 1 1 d . . . . .
C64 C 0.2729(3) 0.9460(3) 0.5521(3) 0.0358(10) Uani 1 1 d . . . . .
C65 C 0.2153(4) 0.9978(3) 0.5363(3) 0.0462(13) Uani 1 1 d . . . . .
H65 H 0.2482 1.0554 0.5564 0.055 Uiso 1 1 calc R U . . .
C66 C 0.1121(4) 0.9673(4) 0.4924(4) 0.0548(15) Uani 1 1 d . . . . .
H66 H 0.0750 1.0039 0.4809 0.066 Uiso 1 1 calc R U . . .
C67 C 0.0627(4) 0.8843(4) 0.4652(3) 0.0517(14) Uani 1 1 d . . . . .
H67 H -0.0090 0.8642 0.4360 0.062 Uiso 1 1 calc R U . . .
C68 C 0.1140(3) 0.8287(3) 0.4789(3) 0.0407(11) Uani 1 1 d . . . . .
C69 C 0.0570(4) 0.7362(3) 0.4522(3) 0.0503(13) Uani 1 1 d . . . . .
H69 H 0.1085 0.7080 0.4674 0.060 Uiso 1 1 calc R U . . .
C70 C 0.0018(5) 0.7153(4) 0.3611(4) 0.080(2) Uani 1 1 d . . . . .
H70A H -0.0551 0.7360 0.3454 0.120 Uiso 1 1 calc R U . . .
H70B H -0.0245 0.6552 0.3444 0.120 Uiso 1 1 calc R U . . .
H70C H 0.0495 0.7412 0.3347 0.120 Uiso 1 1 calc R U . . .
C71 C -0.0160(4) 0.7044(4) 0.4944(4) 0.0713(18) Uani 1 1 d . . . . .
H71A H 0.0213 0.7175 0.5529 0.107 Uiso 1 1 calc R U . . .
H71B H -0.0491 0.6443 0.4781 0.107 Uiso 1 1 calc R U . . .
H71C H -0.0680 0.7305 0.4797 0.107 Uiso 1 1 calc R U . . .
C72 C 0.4118(5) 1.0190(5) 0.6860(4) 0.0730(18) Uani 1 1 d . . . . .
H72A H 0.3845 1.0638 0.6860 0.109 Uiso 1 1 calc R U . . .
H72B H 0.4861 1.0411 0.7142 0.109 Uiso 1 1 calc R U . . .
H72C H 0.3813 0.9763 0.7137 0.109 Uiso 1 1 calc R U . . .
C73 C 0.3863(4) 0.9817(3) 0.5998(4) 0.0497(13) Uani 1 1 d . . . . .
H73 H 0.4131 0.9352 0.6020 0.060 Uiso 1 1 calc R U . . .
C74 C 0.4408(5) 1.0442(5) 0.5588(4) 0.085(2) Uani 1 1 d . . . . .
H74A H 0.4216 1.0203 0.5025 0.128 Uiso 1 1 calc R U . . .
H74B H 0.5148 1.0598 0.5868 0.128 Uiso 1 1 calc R U . . .
H74C H 0.4216 1.0934 0.5606 0.128 Uiso 1 1 calc R U . . .
C75 C 0.7127(6) 0.7849(5) 0.2767(5) 0.096(2) Uani 1 1 d . . . . .
H75A H 0.7070 0.7407 0.2363 0.115 Uiso 1 1 calc R U . . .
H75B H 0.6481 0.7965 0.2582 0.115 Uiso 1 1 calc R U . . .
N1 N 0.3260(2) 0.7811(2) 0.9349(2) 0.0283(8) Uani 1 1 d . . . . .
H1 H 0.3549 0.7569 0.9102 0.034 Uiso 1 1 calc R U . . .
N2 N 0.0061(3) 0.7919(2) 0.9279(2) 0.0371(9) Uani 1 1 d . . . . .
H2 H -0.0602 0.7676 0.9023 0.044 Uiso 1 1 calc R U . . .
N3 N 0.2026(3) 0.6701(2) 0.6510(2) 0.0340(9) Uani 1 1 d . . . . .
N4 N -0.0695(4) 0.4526(3) 0.5542(3) 0.0600(13) Uani 1 1 d . . . . .
N5 N -0.1708(3) 0.4884(3) 0.7077(3) 0.0608(13) Uani 1 1 d . . . . .
N6 N 0.4122(3) 0.5743(2) 0.8733(2) 0.0360(9) Uani 1 1 d . . . . .
H6 H 0.3716 0.6030 0.8688 0.043 Uiso 1 1 calc R U . . .
N7 N 0.7336(3) 0.5881(2) 0.8612(2) 0.0375(9) Uani 1 1 d . . . . .
H7 H 0.7911 0.6240 0.8613 0.045 Uiso 1 1 calc R U . . .
N8 N 0.4207(3) 0.8192(2) 0.7337(2) 0.0354(9) Uani 1 1 d . . . . .
N9 N 0.8438(3) 0.9341(3) 0.9576(4) 0.0805(19) Uani 1 1 d . . . . .
N10 N 0.6725(3) 1.0445(3) 0.8782(2) 0.0417(10) Uani 1 1 d . . . . .
N11 N 0.2780(2) 0.8063(2) 0.5360(2) 0.0269(8) Uani 1 1 d . . . . .
N12 N 0.3935(3) 0.7069(2) 0.5693(2) 0.0301(8) Uani 1 1 d . . . . .
O1 O 0.2276(2) 0.65069(18) 0.82059(18) 0.0324(7) Uani 1 1 d . . . . .
O2 O -0.0878(2) 0.6639(2) 0.8123(2) 0.0442(8) Uani 1 1 d . . . . .
O3 O 0.4620(2) 0.73278(17) 0.87151(17) 0.0302(7) Uani 1 1 d . . . . .
O4 O 0.7845(2) 0.75018(19) 0.8725(2) 0.0449(9) Uani 1 1 d . . . . .
F1 F 0.5766(3) 0.6895(3) 0.0689(3) 0.0883(12) Uani 1 1 d . . . . .
F2 F 0.4098(4) 0.6346(4) 0.0352(3) 0.156(3) Uani 1 1 d . . . . .
F3 F 0.4950(4) 0.7474(3) 0.1259(2) 0.0952(15) Uani 1 1 d . . . . .
F4 F 0.5114(3) 0.63034(19) 0.1607(2) 0.0675(10) Uani 1 1 d . . . . .
Cl1 Cl 0.73094(19) 0.7518(2) 0.36904(19) 0.1515(12) Uani 1 1 d . . . . .
Cl2 Cl 0.8111(2) 0.87125(17) 0.28372(17) 0.1279(9) Uani 1 1 d . . . . .
Cu1 Cu 0.31634(4) 0.74965(3) 0.63563(3) 0.03225(18) Uani 1 1 d . . . . .
B1 B 0.4994(5) 0.6755(4) 0.0970(4) 0.0539(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.231(4) . ?
C1 C2 1.449(6) . ?
C1 C6 1.520(6) . ?
C2 C7 1.428(6) . ?
C2 C3 1.434(5) . ?
C3 O2 1.244(5) . ?
C3 C4 1.512(6) . ?
C4 N2 1.313(5) . ?
C4 C5 1.390(6) . ?
C5 C6 1.391(5) . ?
C5 H5 0.9500 . ?
C6 N1 1.309(5) . ?
C7 C9 1.377(6) . ?
C7 C8 1.447(6) . ?
C8 N5 1.145(6) . ?
C9 C11 1.434(6) . ?
C9 C10 1.456(7) . ?
C10 N4 1.144(6) . ?
C11 N3 1.132(5) . ?
C12 N1 1.470(6) . ?
C12 C13 1.510(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.520(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.516(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N2 1.460(6) . ?
C16 C17 1.465(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.386(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.499(12) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C26 1.429(6) . ?
C20 C25 1.434(5) . ?
C20 C21 1.439(5) . ?
C21 O4 1.233(5) . ?
C21 C22 1.529(6) . ?
C22 N7 1.316(5) . ?
C22 C23 1.381(6) . ?
C23 C24 1.403(5) . ?
C23 H23 0.9500 . ?
C24 N6 1.299(5) . ?
C24 C25 1.516(6) . ?
C25 O3 1.222(4) . ?
C26 C28 1.378(5) . ?
C26 C27 1.440(6) . ?
C27 N9 1.137(6) . ?
C28 C30 1.417(6) . ?
C28 C29 1.427(6) . ?
C29 N10 1.147(6) . ?
C30 N8 1.161(6) . ?
C31 N6 1.464(6) . ?
C31 C32 1.505(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.414(9) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.602(9) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 N7 1.448(5) . ?
C35 C36 1.497(7) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.507(8) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.454(9) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 N12 1.285(5) . ?
C39 C49 1.471(6) . ?
C39 C40 1.516(6) . ?
C40 N11 1.274(5) . ?
C40 C41 1.493(6) . ?
C41 C42 1.376(6) . ?
C41 C50 1.419(6) . ?
C42 C43 1.417(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.383(7) . ?
C43 H43 0.9500 . ?
C44 C45 1.388(6) . ?
C44 H44 0.9500 . ?
C45 C50 1.398(6) . ?
C45 C46 1.422(6) . ?
C46 C47 1.359(7) . ?
C46 H46 0.9500 . ?
C47 C48 1.408(6) . ?
C47 H47 0.9500 . ?
C48 C49 1.367(6) . ?
C48 H48 0.9500 . ?
C49 C50 1.423(6) . ?
C51 C56 1.398(7) . ?
C51 C52 1.423(7) . ?
C51 N12 1.431(5) . ?
C52 C53 1.392(7) . ?
C52 C61 1.512(8) . ?
C53 C54 1.371(9) . ?
C53 H53 0.9500 . ?
C54 C55 1.373(9) . ?
C54 H54 0.9500 . ?
C55 C56 1.412(7) . ?
C55 H55 0.9500 . ?
C56 C57 1.518(7) . ?
C57 C58 1.498(7) . ?
C57 C59 1.509(7) . ?
C57 H57 1.0000 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C60 C61 1.451(9) . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C61 C62 1.541(8) . ?
C61 H61 1.0000 . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
C63 C68 1.405(6) . ?
C63 C64 1.412(6) . ?
C63 N11 1.440(5) . ?
C64 C65 1.398(6) . ?
C64 C73 1.508(7) . ?
C65 C66 1.373(8) . ?
C65 H65 0.9500 . ?
C66 C67 1.367(8) . ?
C66 H66 0.9500 . ?
C67 C68 1.386(6) . ?
C67 H67 0.9500 . ?
C68 C69 1.519(7) . ?
C69 C71 1.498(8) . ?
C69 C70 1.520(8) . ?
C69 H69 1.0000 . ?
C70 H70A 0.9800 . ?
C70 H70B 0.9800 . ?
C70 H70C 0.9800 . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C72 C73 1.515(8) . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
C73 C74 1.504(8) . ?
C73 H73 1.0000 . ?
C74 H74A 0.9800 . ?
C74 H74B 0.9800 . ?
C74 H74C 0.9800 . ?
C75 Cl2 1.691(8) . ?
C75 Cl1 1.728(9) . ?
C75 H75A 0.9900 . ?
C75 H75B 0.9900 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?
N3 Cu1 1.919(4) . ?
N6 H6 0.8800 . ?
N7 H7 0.8800 . ?
N8 Cu1 1.932(4) . ?
N11 Cu1 2.063(3) . ?
N12 Cu1 2.147(3) . ?
F1 B1 1.356(7) . ?
F2 B1 1.357(8) . ?
F3 B1 1.354(7) . ?
F4 B1 1.397(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 C1 C2 124.4(4) . . ?
O1 C1 C6 117.7(4) . . ?
C2 C1 C6 117.9(3) . . ?
C7 C2 C3 119.5(4) . . ?
C7 C2 C1 121.0(3) . . ?
C3 C2 C1 119.3(4) . . ?
O2 C3 C2 123.6(4) . . ?
O2 C3 C4 117.6(3) . . ?
C2 C3 C4 118.8(4) . . ?
N2 C4 C5 124.5(4) . . ?
N2 C4 C3 113.4(4) . . ?
C5 C4 C3 122.0(3) . . ?
C4 C5 C6 119.2(4) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 123.9(4) . . ?
N1 C6 C1 113.9(3) . . ?
C5 C6 C1 122.2(4) . . ?
C9 C7 C2 127.0(4) . . ?
C9 C7 C8 113.9(4) . . ?
C2 C7 C8 119.1(4) . . ?
N5 C8 C7 172.9(5) . . ?
C7 C9 C11 124.3(4) . . ?
C7 C9 C10 120.7(4) . . ?
C11 C9 C10 114.8(4) . . ?
N4 C10 C9 178.2(6) . . ?
N3 C11 C9 174.5(5) . . ?
N1 C12 C13 111.8(3) . . ?
N1 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
N1 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 112.5(3) . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 111.4(4) . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 115.8(5) . . ?
N2 C16 H16A 108.3 . . ?
C17 C16 H16A 108.3 . . ?
N2 C16 H16B 108.3 . . ?
C17 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C18 C17 C16 118.4(10) . . ?
C18 C17 H17A 107.7 . . ?
C16 C17 H17A 107.7 . . ?
C18 C17 H17B 107.7 . . ?
C16 C17 H17B 107.7 . . ?
H17A C17 H17B 107.1 . . ?
C17 C18 C19 111.7(10) . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C26 C20 C25 121.6(3) . . ?
C26 C20 C21 118.1(3) . . ?
C25 C20 C21 120.1(4) . . ?
O4 C21 C20 123.5(4) . . ?
O4 C21 C22 118.2(3) . . ?
C20 C21 C22 118.3(3) . . ?
N7 C22 C23 124.8(4) . . ?
N7 C22 C21 113.5(3) . . ?
C23 C22 C21 121.7(3) . . ?
C22 C23 C24 119.5(4) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
N6 C24 C23 124.5(4) . . ?
N6 C24 C25 113.6(3) . . ?
C23 C24 C25 121.9(4) . . ?
O3 C25 C20 123.9(4) . . ?
O3 C25 C24 117.7(3) . . ?
C20 C25 C24 118.4(3) . . ?
C28 C26 C20 126.4(4) . . ?
C28 C26 C27 113.9(4) . . ?
C20 C26 C27 119.7(3) . . ?
N9 C27 C26 173.2(5) . . ?
C26 C28 C30 121.2(4) . . ?
C26 C28 C29 120.8(4) . . ?
C30 C28 C29 117.0(4) . . ?
N10 C29 C28 178.7(5) . . ?
N8 C30 C28 174.2(4) . . ?
N6 C31 C32 110.8(4) . . ?
N6 C31 H31A 109.5 . . ?
C32 C31 H31A 109.5 . . ?
N6 C31 H31B 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 108.1 . . ?
C33 C32 C31 112.5(6) . . ?
C33 C32 H32A 109.1 . . ?
C31 C32 H32A 109.1 . . ?
C33 C32 H32B 109.1 . . ?
C31 C32 H32B 109.1 . . ?
H32A C32 H32B 107.8 . . ?
C32 C33 C34 112.3(6) . . ?
C32 C33 H33A 109.1 . . ?
C34 C33 H33A 109.1 . . ?
C32 C33 H33B 109.1 . . ?
C34 C33 H33B 109.1 . . ?
H33A C33 H33B 107.9 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N7 C35 C36 112.3(4) . . ?
N7 C35 H35A 109.1 . . ?
C36 C35 H35A 109.1 . . ?
N7 C35 H35B 109.1 . . ?
C36 C35 H35B 109.1 . . ?
H35A C35 H35B 107.9 . . ?
C35 C36 C37 112.4(5) . . ?
C35 C36 H36A 109.1 . . ?
C37 C36 H36A 109.1 . . ?
C35 C36 H36B 109.1 . . ?
C37 C36 H36B 109.1 . . ?
H36A C36 H36B 107.9 . . ?
C38 C37 C36 114.2(7) . . ?
C38 C37 H37A 108.7 . . ?
C36 C37 H37A 108.7 . . ?
C38 C37 H37B 108.7 . . ?
C36 C37 H37B 108.7 . . ?
H37A C37 H37B 107.6 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N12 C39 C49 134.9(4) . . ?
N12 C39 C40 117.3(3) . . ?
C49 C39 C40 107.7(3) . . ?
N11 C40 C41 133.7(4) . . ?
N11 C40 C39 119.7(4) . . ?
C41 C40 C39 106.5(3) . . ?
C42 C41 C50 119.9(4) . . ?
C42 C41 C40 134.3(4) . . ?
C50 C41 C40 105.7(3) . . ?
C41 C42 C43 117.4(4) . . ?
C41 C42 H42 121.3 . . ?
C43 C42 H42 121.3 . . ?
C44 C43 C42 122.2(4) . . ?
C44 C43 H43 118.9 . . ?
C42 C43 H43 118.9 . . ?
C43 C44 C45 121.1(4) . . ?
C43 C44 H44 119.5 . . ?
C45 C44 H44 119.5 . . ?
C44 C45 C50 117.0(4) . . ?
C44 C45 C46 127.7(4) . . ?
C50 C45 C46 115.3(4) . . ?
C47 C46 C45 121.0(4) . . ?
C47 C46 H46 119.5 . . ?
C45 C46 H46 119.5 . . ?
C46 C47 C48 123.1(4) . . ?
C46 C47 H47 118.4 . . ?
C48 C47 H47 118.4 . . ?
C49 C48 C47 117.8(4) . . ?
C49 C48 H48 121.1 . . ?
C47 C48 H48 121.1 . . ?
C48 C49 C50 119.4(4) . . ?
C48 C49 C39 134.8(4) . . ?
C50 C49 C39 105.8(3) . . ?
C45 C50 C41 122.4(4) . . ?
C45 C50 C49 123.3(4) . . ?
C41 C50 C49 114.3(4) . . ?
C56 C51 C52 121.6(4) . . ?
C56 C51 N12 118.4(4) . . ?
C52 C51 N12 119.9(4) . . ?
C53 C52 C51 117.6(5) . . ?
C53 C52 C61 120.2(5) . . ?
C51 C52 C61 122.3(4) . . ?
C54 C53 C52 121.7(5) . . ?
C54 C53 H53 119.1 . . ?
C52 C53 H53 119.1 . . ?
C53 C54 C55 120.2(5) . . ?
C53 C54 H54 119.9 . . ?
C55 C54 H54 119.9 . . ?
C54 C55 C56 121.5(6) . . ?
C54 C55 H55 119.3 . . ?
C56 C55 H55 119.3 . . ?
C51 C56 C55 117.4(5) . . ?
C51 C56 C57 123.0(4) . . ?
C55 C56 C57 119.5(5) . . ?
C58 C57 C59 110.8(5) . . ?
C58 C57 C56 112.0(4) . . ?
C59 C57 C56 112.7(5) . . ?
C58 C57 H57 107.0 . . ?
C59 C57 H57 107.0 . . ?
C56 C57 H57 107.0 . . ?
C57 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C57 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C57 C59 H59A 109.5 . . ?
C57 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
C57 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C61 C60 H60A 109.5 . . ?
C61 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C61 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C60 C61 C52 111.7(5) . . ?
C60 C61 C62 109.7(6) . . ?
C52 C61 C62 111.9(5) . . ?
C60 C61 H61 107.8 . . ?
C52 C61 H61 107.8 . . ?
C62 C61 H61 107.8 . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C61 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C68 C63 C64 121.9(4) . . ?
C68 C63 N11 119.9(4) . . ?
C64 C63 N11 118.1(4) . . ?
C65 C64 C63 117.1(4) . . ?
C65 C64 C73 120.0(4) . . ?
C63 C64 C73 122.9(4) . . ?
C66 C65 C64 121.3(5) . . ?
C66 C65 H65 119.3 . . ?
C64 C65 H65 119.3 . . ?
C67 C66 C65 120.3(4) . . ?
C67 C66 H66 119.9 . . ?
C65 C66 H66 119.9 . . ?
C66 C67 C68 121.9(5) . . ?
C66 C67 H67 119.0 . . ?
C68 C67 H67 119.0 . . ?
C67 C68 C63 117.3(5) . . ?
C67 C68 C69 121.2(4) . . ?
C63 C68 C69 121.4(4) . . ?
C71 C69 C68 111.2(5) . . ?
C71 C69 C70 110.8(5) . . ?
C68 C69 C70 111.0(5) . . ?
C71 C69 H69 107.9 . . ?
C68 C69 H69 107.9 . . ?
C70 C69 H69 107.9 . . ?
C69 C70 H70A 109.5 . . ?
C69 C70 H70B 109.5 . . ?
H70A C70 H70B 109.5 . . ?
C69 C70 H70C 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
C69 C71 H71A 109.5 . . ?
C69 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C69 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C73 C72 H72A 109.5 . . ?
C73 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
C73 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
C74 C73 C64 111.7(5) . . ?
C74 C73 C72 110.1(5) . . ?
C64 C73 C72 112.9(4) . . ?
C74 C73 H73 107.3 . . ?
C64 C73 H73 107.3 . . ?
C72 C73 H73 107.3 . . ?
C73 C74 H74A 109.5 . . ?
C73 C74 H74B 109.5 . . ?
H74A C74 H74B 109.5 . . ?
C73 C74 H74C 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
Cl2 C75 Cl1 110.7(5) . . ?
Cl2 C75 H75A 109.5 . . ?
Cl1 C75 H75A 109.5 . . ?
Cl2 C75 H75B 109.5 . . ?
Cl1 C75 H75B 109.5 . . ?
H75A C75 H75B 108.1 . . ?
C6 N1 C12 123.3(3) . . ?
C6 N1 H1 118.3 . . ?
C12 N1 H1 118.3 . . ?
C4 N2 C16 126.5(4) . . ?
C4 N2 H2 116.7 . . ?
C16 N2 H2 116.7 . . ?
C11 N3 Cu1 174.5(4) . . ?
C24 N6 C31 124.5(4) . . ?
C24 N6 H6 117.7 . . ?
C31 N6 H6 117.7 . . ?
C22 N7 C35 127.2(4) . . ?
C22 N7 H7 116.4 . . ?
C35 N7 H7 116.4 . . ?
C30 N8 Cu1 161.3(3) . . ?
C40 N11 C63 120.0(3) . . ?
C40 N11 Cu1 111.5(3) . . ?
C63 N11 Cu1 128.4(3) . . ?
C39 N12 C51 120.7(3) . . ?
C39 N12 Cu1 109.6(3) . . ?
C51 N12 Cu1 129.7(3) . . ?
N3 Cu1 N8 114.53(15) . . ?
N3 Cu1 N11 114.84(15) . . ?
N8 Cu1 N11 116.80(15) . . ?
N3 Cu1 N12 118.45(14) . . ?
N8 Cu1 N12 106.82(14) . . ?
N11 Cu1 N12 81.09(13) . . ?
F3 B1 F1 111.1(5) . . ?
F3 B1 F2 108.2(6) . . ?
F1 B1 F2 108.6(5) . . ?
F3 B1 F4 106.4(5) . . ?
F1 B1 F4 112.3(5) . . ?
F2 B1 F4 110.2(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 -5.7(6) . . . . ?
C6 C1 C2 C7 175.9(4) . . . . ?
O1 C1 C2 C3 168.8(4) . . . . ?
C6 C1 C2 C3 -9.6(6) . . . . ?
C7 C2 C3 O2 2.1(7) . . . . ?
C1 C2 C3 O2 -172.5(4) . . . . ?
C7 C2 C3 C4 -176.2(4) . . . . ?
C1 C2 C3 C4 9.3(6) . . . . ?
O2 C3 C4 N2 -5.4(6) . . . . ?
C2 C3 C4 N2 173.0(4) . . . . ?
O2 C3 C4 C5 176.4(4) . . . . ?
C2 C3 C4 C5 -5.2(6) . . . . ?
N2 C4 C5 C6 -176.5(4) . . . . ?
C3 C4 C5 C6 1.6(6) . . . . ?
C4 C5 C6 N1 178.4(4) . . . . ?
C4 C5 C6 C1 -2.0(6) . . . . ?
O1 C1 C6 N1 7.2(5) . . . . ?
C2 C1 C6 N1 -174.3(4) . . . . ?
O1 C1 C6 C5 -172.4(4) . . . . ?
C2 C1 C6 C5 6.1(6) . . . . ?
C3 C2 C7 C9 151.5(4) . . . . ?
C1 C2 C7 C9 -34.1(7) . . . . ?
C3 C2 C7 C8 -26.9(6) . . . . ?
C1 C2 C7 C8 147.6(4) . . . . ?
C2 C7 C9 C11 -7.1(7) . . . . ?
C8 C7 C9 C11 171.3(4) . . . . ?
C2 C7 C9 C10 177.5(4) . . . . ?
C8 C7 C9 C10 -4.1(6) . . . . ?
N1 C12 C13 C14 -175.1(4) . . . . ?
C12 C13 C14 C15 177.1(4) . . . . ?
N2 C16 C17 C18 -54.7(12) . . . . ?
C16 C17 C18 C19 -177.1(8) . . . . ?
C26 C20 C21 O4 -4.9(7) . . . . ?
C25 C20 C21 O4 -179.9(4) . . . . ?
C26 C20 C21 C22 177.8(4) . . . . ?
C25 C20 C21 C22 2.8(6) . . . . ?
O4 C21 C22 N7 -2.9(6) . . . . ?
C20 C21 C22 N7 174.6(4) . . . . ?
O4 C21 C22 C23 177.6(4) . . . . ?
C20 C21 C22 C23 -5.0(6) . . . . ?
N7 C22 C23 C24 -176.7(4) . . . . ?
C21 C22 C23 C24 2.8(6) . . . . ?
C22 C23 C24 N6 -179.1(4) . . . . ?
C22 C23 C24 C25 1.4(6) . . . . ?
C26 C20 C25 O3 2.7(7) . . . . ?
C21 C20 C25 O3 177.5(4) . . . . ?
C26 C20 C25 C24 -173.7(4) . . . . ?
C21 C20 C25 C24 1.1(6) . . . . ?
N6 C24 C25 O3 0.4(6) . . . . ?
C23 C24 C25 O3 179.9(4) . . . . ?
N6 C24 C25 C20 177.0(4) . . . . ?
C23 C24 C25 C20 -3.5(6) . . . . ?
C25 C20 C26 C28 -32.7(6) . . . . ?
C21 C20 C26 C28 152.4(4) . . . . ?
C25 C20 C26 C27 145.3(4) . . . . ?
C21 C20 C26 C27 -29.6(6) . . . . ?
C20 C26 C28 C30 -16.9(6) . . . . ?
C27 C26 C28 C30 165.0(4) . . . . ?
C20 C26 C28 C29 175.2(4) . . . . ?
C27 C26 C28 C29 -2.9(6) . . . . ?
N6 C31 C32 C33 80.9(7) . . . . ?
C31 C32 C33 C34 -172.6(5) . . . . ?
N7 C35 C36 C37 -178.6(5) . . . . ?
C35 C36 C37 C38 -179.9(6) . . . . ?
N12 C39 C40 N11 -3.5(6) . . . . ?
C49 C39 C40 N11 180.0(4) . . . . ?
N12 C39 C40 C41 174.6(4) . . . . ?
C49 C39 C40 C41 -1.9(5) . . . . ?
N11 C40 C41 C42 2.2(9) . . . . ?
C39 C40 C41 C42 -175.6(5) . . . . ?
N11 C40 C41 C50 178.5(5) . . . . ?
C39 C40 C41 C50 0.7(5) . . . . ?
C50 C41 C42 C43 1.7(7) . . . . ?
C40 C41 C42 C43 177.6(5) . . . . ?
C41 C42 C43 C44 -0.7(8) . . . . ?
C42 C43 C44 C45 -0.5(8) . . . . ?
C43 C44 C45 C50 0.6(7) . . . . ?
C43 C44 C45 C46 -179.4(5) . . . . ?
C44 C45 C46 C47 179.3(5) . . . . ?
C50 C45 C46 C47 -0.7(7) . . . . ?
C45 C46 C47 C48 0.3(8) . . . . ?
C46 C47 C48 C49 -0.4(7) . . . . ?
C47 C48 C49 C50 0.8(7) . . . . ?
C47 C48 C49 C39 -177.5(5) . . . . ?
N12 C39 C49 C48 5.1(9) . . . . ?
C40 C39 C49 C48 -179.3(5) . . . . ?
N12 C39 C49 C50 -173.4(5) . . . . ?
C40 C39 C49 C50 2.2(5) . . . . ?
C44 C45 C50 C41 0.4(7) . . . . ?
C46 C45 C50 C41 -179.5(4) . . . . ?
C44 C45 C50 C49 -178.8(4) . . . . ?
C46 C45 C50 C49 1.2(7) . . . . ?
C42 C41 C50 C45 -1.6(7) . . . . ?
C40 C41 C50 C45 -178.6(4) . . . . ?
C42 C41 C50 C49 177.7(4) . . . . ?
C40 C41 C50 C49 0.7(5) . . . . ?
C48 C49 C50 C45 -1.3(7) . . . . ?
C39 C49 C50 C45 177.5(4) . . . . ?
C48 C49 C50 C41 179.4(4) . . . . ?
C39 C49 C50 C41 -1.9(5) . . . . ?
C56 C51 C52 C53 -2.7(7) . . . . ?
N12 C51 C52 C53 173.9(4) . . . . ?
C56 C51 C52 C61 177.8(4) . . . . ?
N12 C51 C52 C61 -5.6(7) . . . . ?
C51 C52 C53 C54 2.2(8) . . . . ?
C61 C52 C53 C54 -178.3(5) . . . . ?
C52 C53 C54 C55 -1.1(9) . . . . ?
C53 C54 C55 C56 0.3(9) . . . . ?
C52 C51 C56 C55 2.0(7) . . . . ?
N12 C51 C56 C55 -174.7(4) . . . . ?
C52 C51 C56 C57 -175.2(4) . . . . ?
N12 C51 C56 C57 8.2(6) . . . . ?
C54 C55 C56 C51 -0.8(8) . . . . ?
C54 C55 C56 C57 176.5(5) . . . . ?
C51 C56 C57 C58 112.2(5) . . . . ?
C55 C56 C57 C58 -64.8(6) . . . . ?
C51 C56 C57 C59 -122.1(5) . . . . ?
C55 C56 C57 C59 60.8(6) . . . . ?
C53 C52 C61 C60 -80.1(7) . . . . ?
C51 C52 C61 C60 99.4(6) . . . . ?
C53 C52 C61 C62 43.3(7) . . . . ?
C51 C52 C61 C62 -137.2(5) . . . . ?
C68 C63 C64 C65 -2.9(7) . . . . ?
N11 C63 C64 C65 179.8(4) . . . . ?
C68 C63 C64 C73 177.8(4) . . . . ?
N11 C63 C64 C73 0.5(6) . . . . ?
C63 C64 C65 C66 0.0(7) . . . . ?
C73 C64 C65 C66 179.4(5) . . . . ?
C64 C65 C66 C67 2.2(8) . . . . ?
C65 C66 C67 C68 -1.5(8) . . . . ?
C66 C67 C68 C63 -1.3(8) . . . . ?
C66 C67 C68 C69 176.7(5) . . . . ?
C64 C63 C68 C67 3.5(7) . . . . ?
N11 C63 C68 C67 -179.2(4) . . . . ?
C64 C63 C68 C69 -174.4(4) . . . . ?
N11 C63 C68 C69 2.8(6) . . . . ?
C67 C68 C69 C71 -62.5(6) . . . . ?
C63 C68 C69 C71 115.4(5) . . . . ?
C67 C68 C69 C70 61.3(6) . . . . ?
C63 C68 C69 C70 -120.8(5) . . . . ?
C65 C64 C73 C74 -60.2(7) . . . . ?
C63 C64 C73 C74 119.1(5) . . . . ?
C65 C64 C73 C72 64.5(6) . . . . ?
C63 C64 C73 C72 -116.2(5) . . . . ?
C5 C6 N1 C12 2.6(6) . . . . ?
C1 C6 N1 C12 -177.0(4) . . . . ?
C13 C12 N1 C6 -169.1(4) . . . . ?
C5 C4 N2 C16 0.4(7) . . . . ?
C3 C4 N2 C16 -177.7(4) . . . . ?
C17 C16 N2 C4 -94.8(7) . . . . ?
C23 C24 N6 C31 6.9(7) . . . . ?
C25 C24 N6 C31 -173.6(4) . . . . ?
C32 C31 N6 C24 171.7(5) . . . . ?
C23 C22 N7 C35 0.7(8) . . . . ?
C21 C22 N7 C35 -178.9(4) . . . . ?
C36 C35 N7 C22 -134.8(5) . . . . ?
C41 C40 N11 C63 1.9(7) . . . . ?
C39 C40 N11 C63 179.5(4) . . . . ?
C41 C40 N11 Cu1 178.3(4) . . . . ?
C39 C40 N11 Cu1 -4.1(5) . . . . ?
C68 C63 N11 C40 83.6(5) . . . . ?
C64 C63 N11 C40 -99.1(5) . . . . ?
C68 C63 N11 Cu1 -92.1(5) . . . . ?
C64 C63 N11 Cu1 85.2(4) . . . . ?
C49 C39 N12 C51 2.9(8) . . . . ?
C40 C39 N12 C51 -172.3(4) . . . . ?
C49 C39 N12 Cu1 -176.1(4) . . . . ?
C40 C39 N12 Cu1 8.6(5) . . . . ?
C56 C51 N12 C39 -108.6(5) . . . . ?
C52 C51 N12 C39 74.7(6) . . . . ?
C56 C51 N12 Cu1 70.2(5) . . . . ?
C52 C51 N12 Cu1 -106.5(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
N1 H1 O3 0.88 2.07 2.921(4) 162.0 .
N2 H2 O4 0.88 2.10 2.926(5) 156.3 1_455
N6 H6 O1 0.88 2.43 3.282(4) 162.7 .
N7 H7 O2 0.88 2.19 2.989(5) 151.3 1_655

_refine_diff_density_max         1.425
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.098

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.007 0.097 0.277 215.9 62.1
2 0.006 -0.097 0.723 215.3 61.5
3 0.131 0.674 0.251 9.3 1.5
4 0.252 0.191 0.918 11.0 2.1
5 0.748 0.809 0.082 10.4 2.4
6 0.869 0.326 0.749 9.3 1.6
_platon_squeeze_details          
;
 The residual electron density was assigned to two molecules of the
 dichloromethane solvent [131/2 = 66 e per asymmetric unit; two molecules
 of CH2Cl2 would give 84e].
;

_shelxl_version_number           2013-4

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

data_pbtk101123
_database_code_depnum_ccdc_archive 'CCDC 1039322'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H40 Cu N10 O4'
_chemical_formula_sum            'C38 H40 Cu N10 O4'
_chemical_formula_weight         764.34

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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   11.0282(5)
_cell_length_b                   13.5670(7)
_cell_length_c                   14.6751(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.707(2)
_cell_angle_gamma                90.00
_cell_volume                     2079.69(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7685
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             798
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74761
_exptl_absorpt_correction_T_max  0.98146
_exptl_absorpt_process_details   'MULscanABS in PLATON (Spek, 2003)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12679
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4761
_reflns_number_gt                3454
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.1367P)²+1.9359P] 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         4761
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0753
_refine_ls_wR_factor_ref         0.2349
_refine_ls_wR_factor_gt          0.2102
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6563(3) 0.9637(3) 0.1816(2) 0.0187(7) Uani 1 1 d . . .
C2 C 0.7153(3) 0.9222(3) 0.2734(2) 0.0198(7) Uani 1 1 d . . .
C3 C 0.8258(3) 0.9698(3) 0.3402(2) 0.0215(8) Uani 1 1 d . . .
C4 C 0.8756(3) 1.0626(3) 0.3070(2) 0.0224(8) Uani 1 1 d . . .
C5 C 0.8233(3) 1.0978(3) 0.2151(2) 0.0226(8) Uani 1 1 d . . .
H5 H 0.8599 1.1540 0.1954 0.027 Uiso 1 1 calc R . .
C6 C 0.7161(3) 1.0518(3) 0.1495(2) 0.0187(7) Uani 1 1 d . . .
C7 C 0.7038(3) 1.1541(3) 0.0125(3) 0.0241(8) Uani 1 1 d . . .
H7A H 0.6836 1.1382 -0.0567 0.029 Uiso 1 1 calc R . .
H7B H 0.7980 1.1592 0.0408 0.029 Uiso 1 1 calc R . .
C8 C 0.6441(6) 1.2520(4) 0.0225(5) 0.0572(16) Uani 1 1 d . B .
H8A H 0.6596 1.2658 0.0915 0.069 Uiso 1 1 calc R . .
H8B H 0.5504 1.2481 -0.0095 0.069 Uiso 1 1 calc R . .
C9 C 0.6975(8) 1.3359(5) -0.0212(7) 0.101(3) Uani 1 1 d . . .
H9A H 0.6554 1.3365 -0.0918 0.122 Uiso 1 1 calc R A 1
H9B H 0.7904 1.3257 -0.0083 0.122 Uiso 1 1 calc R A 1
C10 C 0.6748(18) 1.4391(10) 0.0225(16) 0.101(3) Uani 0.50 1 d P B 1
H10A H 0.5940 1.4371 0.0369 0.152 Uiso 0.50 1 calc PR B 1
H10B H 0.6709 1.4915 -0.0243 0.152 Uiso 0.50 1 calc PR B 1
H10C H 0.7455 1.4522 0.0817 0.152 Uiso 0.50 1 calc PR B 1
C10B C 0.5890(17) 1.4197(10) -0.0534(16) 0.101(3) Uani 0.50 1 d P B 2
H10D H 0.5117 1.3920 -0.0998 0.152 Uiso 0.50 1 calc PR B 2
H10E H 0.6203 1.4745 -0.0832 0.152 Uiso 0.50 1 calc PR B 2
H10F H 0.5691 1.4436 0.0032 0.152 Uiso 0.50 1 calc PR B 2
C11 C 1.0311(4) 1.1975(3) 0.3645(3) 0.0330(10) Uani 1 1 d . . .
H11A H 1.0499 1.1975 0.3029 0.040 Uiso 1 1 calc R . .
H11B H 1.1133 1.2045 0.4172 0.040 Uiso 1 1 calc R . .
C12 C 0.9463(5) 1.2847(4) 0.3662(4) 0.0448(12) Uani 1 1 d . . .
H12A H 0.8635 1.2770 0.3142 0.054 Uiso 1 1 calc R . .
H12B H 0.9287 1.2853 0.4283 0.054 Uiso 1 1 calc R . .
C13 C 1.0055(8) 1.3818(5) 0.3536(7) 0.099(2) Uani 1 1 d . . .
H13A H 1.0228 1.3815 0.2914 0.119 Uiso 1 1 calc R . .
H13B H 1.0884 1.3896 0.4055 0.119 Uiso 1 1 calc R . .
C14 C 0.9197(8) 1.4687(5) 0.3558(8) 0.099(2) Uani 1 1 d . . .
H14A H 0.9620 1.5301 0.3479 0.148 Uiso 1 1 calc R . .
H14B H 0.9033 1.4698 0.4176 0.148 Uiso 1 1 calc R . .
H14C H 0.8384 1.4622 0.3034 0.148 Uiso 1 1 calc R . .
C15 C 0.6600(3) 0.8364(3) 0.3025(2) 0.0220(8) Uani 1 1 d . . .
C16 C 0.5221(4) 0.8297(4) 0.2749(3) 0.0354(10) Uani 1 1 d . . .
C17 C 0.7278(4) 0.7603(3) 0.3563(3) 0.0247(8) Uani 1 1 d . . .
C18 C 0.8615(4) 0.7502(3) 0.3733(3) 0.0286(9) Uani 1 1 d . . .
C19 C 0.6677(4) 0.6821(3) 0.3917(3) 0.0319(9) Uani 1 1 d . . .
N1 N 0.6578(3) 1.0741(2) 0.06012(19) 0.0193(6) Uani 1 1 d . . .
N2 N 0.9725(3) 1.1037(3) 0.3751(2) 0.0296(8) Uani 1 1 d . . .
H2 H 1.0033 1.0723 0.4301 0.036 Uiso 1 1 calc R . .
N3 N 0.4136(4) 0.8223(4) 0.2571(3) 0.0622(14) Uani 1 1 d . . .
N4 N 0.9670(4) 0.7369(3) 0.3826(3) 0.0438(10) Uani 1 1 d . . .
N5 N 0.6228(4) 0.6196(3) 0.4209(3) 0.0477(10) Uani 1 1 d . . .
O1 O 0.5582(2) 0.92625(19) 0.12232(17) 0.0246(6) Uani 1 1 d . . .
O2 O 0.8778(3) 0.9415(2) 0.42245(17) 0.0292(6) Uani 1 1 d . . .
Cu1 Cu 0.5000 1.0000 0.0000 0.0226(2) Uani 1 2 d S . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.257(4) . ?
C1 C2 1.412(5) . ?
C1 C6 1.511(5) . ?
C2 C15 1.440(5) . ?
C2 C3 1.448(5) . ?
C3 O2 1.220(4) . ?
C3 C4 1.515(5) . ?
C4 N2 1.329(5) . ?
C4 C5 1.371(5) . ?
C5 C6 1.409(5) . ?
C5 H5 0.9500 . ?
C6 N1 1.298(4) . ?
C7 N1 1.467(4) . ?
C7 C8 1.510(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.515(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.593(17) . ?
C9 C10B 1.607(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11 N2 1.457(5) . ?
C11 C12 1.514(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.508(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.519(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C17 1.368(5) . ?
C15 C16 1.446(5) . ?
C16 N3 1.144(6) . ?
C17 C18 1.421(5) . ?
C17 C19 1.433(6) . ?
C18 N4 1.141(5) . ?
C19 N5 1.134(6) . ?
N1 Cu1 1.958(3) . ?
N2 H2 0.8800 . ?
O1 Cu1 1.974(2) . ?
Cu1 N1 1.958(3) 3_675 ?
Cu1 O1 1.974(2) 3_675 ?

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 C1 C2 122.0(3) . . ?
O1 C1 C6 117.9(3) . . ?
C2 C1 C6 119.9(3) . . ?
C1 C2 C15 119.7(3) . . ?
C1 C2 C3 119.9(3) . . ?
C15 C2 C3 120.3(3) . . ?
O2 C3 C2 123.8(3) . . ?
O2 C3 C4 118.4(3) . . ?
C2 C3 C4 117.7(3) . . ?
N2 C4 C5 125.1(3) . . ?
N2 C4 C3 113.2(3) . . ?
C5 C4 C3 121.7(3) . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
N1 C6 C5 128.4(3) . . ?
N1 C6 C1 112.1(3) . . ?
C5 C6 C1 119.5(3) . . ?
N1 C7 C8 112.1(3) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 112.3(4) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 111.0(7) . . ?
C8 C9 C10B 107.6(7) . . ?
C10 C9 C10B 45.5(9) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C10B C9 H9A 68.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C10B C9 H9B 141.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
C9 C10B H10D 109.5 . . ?
C9 C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C9 C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
N2 C11 C12 112.5(4) . . ?
N2 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 112.7(4) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 112.2(5) . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C15 C2 125.2(3) . . ?
C17 C15 C16 116.4(3) . . ?
C2 C15 C16 118.4(3) . . ?
N3 C16 C15 176.8(4) . . ?
C15 C17 C18 121.2(3) . . ?
C15 C17 C19 122.5(4) . . ?
C18 C17 C19 116.1(3) . . ?
N4 C18 C17 175.3(5) . . ?
N5 C19 C17 178.5(5) . . ?
C6 N1 C7 121.3(3) . . ?
C6 N1 Cu1 114.6(2) . . ?
C7 N1 Cu1 124.0(2) . . ?
C4 N2 C11 124.3(3) . . ?
C4 N2 H2 117.8 . . ?
C11 N2 H2 117.8 . . ?
C1 O1 Cu1 112.4(2) . . ?
N1 Cu1 N1 180.0 . 3_675 ?
N1 Cu1 O1 82.40(11) . . ?
N1 Cu1 O1 97.60(11) 3_675 . ?
N1 Cu1 O1 97.60(11) . 3_675 ?
N1 Cu1 O1 82.40(11) 3_675 3_675 ?
O1 Cu1 O1 180.00(13) . 3_675 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C15 -2.3(5) . . . . ?
C6 C1 C2 C15 -178.0(3) . . . . ?
O1 C1 C2 C3 -178.2(3) . . . . ?
C6 C1 C2 C3 6.0(5) . . . . ?
C1 C2 C3 O2 175.9(4) . . . . ?
C15 C2 C3 O2 0.0(6) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C15 C2 C3 C4 -177.1(3) . . . . ?
O2 C3 C4 N2 -0.9(5) . . . . ?
C2 C3 C4 N2 176.4(3) . . . . ?
O2 C3 C4 C5 178.9(4) . . . . ?
C2 C3 C4 C5 -3.8(6) . . . . ?
N2 C4 C5 C6 -176.6(4) . . . . ?
C3 C4 C5 C6 3.6(6) . . . . ?
C4 C5 C6 N1 -178.1(4) . . . . ?
C4 C5 C6 C1 1.3(5) . . . . ?
O1 C1 C6 N1 -2.8(5) . . . . ?
C2 C1 C6 N1 173.2(3) . . . . ?
O1 C1 C6 C5 177.8(3) . . . . ?
C2 C1 C6 C5 -6.3(5) . . . . ?
N1 C7 C8 C9 176.4(6) . . . . ?
C7 C8 C9 C10 -158.9(10) . . . . ?
C7 C8 C9 C10B 152.9(10) . . . . ?
N2 C11 C12 C13 -179.0(5) . . . . ?
C11 C12 C13 C14 -179.8(7) . . . . ?
C1 C2 C15 C17 142.9(4) . . . . ?
C3 C2 C15 C17 -41.2(5) . . . . ?
C1 C2 C15 C16 -38.4(5) . . . . ?
C3 C2 C15 C16 137.5(4) . . . . ?
C2 C15 C17 C18 -12.4(6) . . . . ?
C16 C15 C17 C18 168.9(4) . . . . ?
C2 C15 C17 C19 173.1(4) . . . . ?
C16 C15 C17 C19 -5.7(6) . . . . ?
C5 C6 N1 C7 2.6(6) . . . . ?
C1 C6 N1 C7 -176.9(3) . . . . ?
C5 C6 N1 Cu1 -173.0(3) . . . . ?
C1 C6 N1 Cu1 7.5(4) . . . . ?
C8 C7 N1 C6 -90.2(5) . . . . ?
C8 C7 N1 Cu1 85.0(4) . . . . ?
C5 C4 N2 C11 5.3(7) . . . . ?
C3 C4 N2 C11 -174.9(4) . . . . ?
C12 C11 N2 C4 72.7(5) . . . . ?
C2 C1 O1 Cu1 -179.2(3) . . . . ?
C6 C1 O1 Cu1 -3.4(4) . . . . ?
C6 N1 Cu1 O1 -7.5(3) . . . . ?
C7 N1 Cu1 O1 177.0(3) . . . . ?
C6 N1 Cu1 O1 172.5(3) . . . 3_675 ?
C7 N1 Cu1 O1 -3.0(3) . . . 3_675 ?
C1 O1 Cu1 N1 5.7(3) . . . . ?
C1 O1 Cu1 N1 -174.3(3) . . . 3_675 ?

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
N2 H2 O2 0.88 2.15 2.964(4) 153.9 3_776

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.492
_refine_diff_density_min         -1.193
_refine_diff_density_rms         0.235

