# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_rad200_0m_a_final
_database_code_depnum_ccdc_archive 'CCDC 1053391'
_audit_update_record             
;
2015-05-10 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_audit_creation_date             2015-03-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C15 H3 Cu3 F18 N6), 2(C3 H3)'
_chemical_formula_sum            'C36 H12 Cu6 F36 N12'
_chemical_formula_weight         1677.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.560(4)
_cell_length_b                   12.620(5)
_cell_length_c                   21.550(8)
_cell_angle_alpha                88.897(7)
_cell_angle_beta                 84.185(7)
_cell_angle_gamma                87.425(7)
_cell_volume                     2583.8(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.72
_cell_measurement_theta_min      2.96
_shelx_estimated_absorpt_T_max   0.752
_shelx_estimated_absorpt_T_min   0.433
_exptl_absorpt_coefficient_mu    2.600
_exptl_absorpt_correction_T_max  0.8789
_exptl_absorpt_correction_T_min  0.5315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0516 before and 0.0418 after correction.
The Ratio of minimum to maximum transmission is 0.6047.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platy
_exptl_crystal_F_000             1620
_exptl_crystal_size_max          0.387
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.116
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            28553
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.962
_diffrn_ambient_temperature      150.03
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9039
_reflns_number_total             11227
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.992
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     867
_refine_ls_number_reflns         11227
_refine_ls_number_restraints     1122
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+3.0821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1056
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 F1, F2, F3, F4, F5, F6, F7, F8, F9, F10, F11, F12, F13, F14, F15, F16, F17,
 F18, F19, F20, F21, F22, F23, F24, F25, F26, F27, F28, F29, F30, F31, F32, F33,
  F34, F35, F36, F7A, F9A, F8A, F34A, F35A, F36A, C1, C2, C3, C4, C5, C6, C7,
 C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23,
 C24, C25, C26, C27, C28, C29, C30, C31, C32, C33, C34, C35, C36
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F7 \\sim F8 \\sim F9
\\sim F10 \\sim F11 \\sim F12 \\sim F13 \\sim F14 \\sim F15 \\sim F16 \\sim F17
\\sim F18 \\sim F19 \\sim F20 \\sim F21 \\sim F22 \\sim F23 \\sim F24 \\sim F25
\\sim F26 \\sim F27 \\sim F28 \\sim F29 \\sim F30 \\sim F31 \\sim F32 \\sim F33
\\sim F34 \\sim F35 \\sim F36 \\sim F7A \\sim F9A \\sim F8A \\sim F34A \\sim
F35A \\sim F36A \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7
\\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15
\\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23
\\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31
\\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq,
Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq,
Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq,
Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq,
Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F7) \\sim
Ueq, Uanis(F8) \\sim Ueq, Uanis(F9) \\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F11)
\\sim Ueq, Uanis(F12) \\sim Ueq, Uanis(F13) \\sim Ueq, Uanis(F14) \\sim Ueq,
Uanis(F15) \\sim Ueq, Uanis(F16) \\sim Ueq, Uanis(F17) \\sim Ueq, Uanis(F18)
\\sim Ueq, Uanis(F19) \\sim Ueq, Uanis(F20) \\sim Ueq, Uanis(F21) \\sim Ueq,
Uanis(F22) \\sim Ueq, Uanis(F23) \\sim Ueq, Uanis(F24) \\sim Ueq, Uanis(F25)
\\sim Ueq, Uanis(F26) \\sim Ueq, Uanis(F27) \\sim Ueq, Uanis(F28) \\sim Ueq,
Uanis(F29) \\sim Ueq, Uanis(F30) \\sim Ueq, Uanis(F31) \\sim Ueq, Uanis(F32)
\\sim Ueq, Uanis(F33) \\sim Ueq, Uanis(F34) \\sim Ueq, Uanis(F35) \\sim Ueq,
Uanis(F36) \\sim Ueq, Uanis(F7A) \\sim Ueq, Uanis(F9A) \\sim Ueq, Uanis(F8A)
\\sim Ueq, Uanis(F34A) \\sim Ueq, Uanis(F35A) \\sim Ueq, Uanis(F36A) \\sim Ueq:
with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Sof(F7)=Sof(F9)=Sof(F8A)=1-FVAR(1)
 Sof(F8)=Sof(F7A)=Sof(F9A)=FVAR(1)
 Sof(F34A)=Sof(F35A)=Sof(F36A)=1-FVAR(2)
 Sof(F34)=Sof(F35)=Sof(F36)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C12(H12), C17(H17), C22(H22), C27(H27), C31(H31), C32(H32),
 C33(H33), C34(H34), C35(H35), C36(H36)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.15702(4) -0.11969(3) 0.47146(2) 0.03624(10) Uani 1 1 d . . . . .
Cu2 Cu 0.13647(4) 0.07486(3) 0.56692(2) 0.03874(10) Uani 1 1 d . . . . .
Cu3 Cu 0.22793(4) 0.11613(3) 0.42004(2) 0.03725(10) Uani 1 1 d . . . . .
F1 F 0.2610(3) -0.3622(2) 0.54073(17) 0.0936(10) Uani 1 1 d . U . . .
F2 F 0.0583(3) -0.3486(2) 0.51208(17) 0.0904(9) Uani 1 1 d . U . . .
F3 F 0.0859(5) -0.4179(3) 0.60036(18) 0.1338(17) Uani 1 1 d . U . . .
F4 F 0.0254(5) -0.0836(3) 0.76198(12) 0.1184(13) Uani 1 1 d . U . . .
F5 F 0.0139(3) 0.0553(3) 0.70456(12) 0.0892(10) Uani 1 1 d . U . . .
F6 F 0.2128(3) -0.0103(3) 0.72354(14) 0.0854(8) Uani 1 1 d . U . . .
F7 F 0.3120(14) 0.3783(8) 0.6528(4) 0.120(3) Uani 0.487(6) 1 d . U P A 1
F8 F 0.2979(14) 0.2117(6) 0.6602(4) 0.102(3) Uani 0.513(6) 1 d . U P A 1
F9 F 0.1166(11) 0.3053(14) 0.6615(4) 0.122(4) Uani 0.487(6) 1 d . U P A 1
F10 F 0.4045(7) 0.4518(3) 0.4103(2) 0.175(2) Uani 1 1 d . U . . .
F11 F 0.4379(7) 0.3036(4) 0.3791(2) 0.176(2) Uani 1 1 d . U . . .
F12 F 0.2505(6) 0.3736(7) 0.3709(2) 0.221(3) Uani 1 1 d . U . . .
F13 F 0.2600(4) 0.1653(2) 0.27291(16) 0.1003(11) Uani 1 1 d . U . . .
F14 F 0.4705(4) 0.1285(3) 0.28879(18) 0.1132(12) Uani 1 1 d . U . . .
F15 F 0.3876(6) 0.0641(3) 0.21048(13) 0.1384(17) Uani 1 1 d . U . . .
F16 F 0.3551(4) -0.3152(2) 0.39565(17) 0.1036(12) Uani 1 1 d . U . . .
F17 F 0.3077(5) -0.3370(3) 0.30405(15) 0.1239(15) Uani 1 1 d . U . . .
F18 F 0.1483(4) -0.3145(3) 0.3772(3) 0.1348(17) Uani 1 1 d . U . . .
N1 N 0.1146(3) -0.1447(2) 0.55705(13) 0.0400(6) Uani 1 1 d . . . . .
N2 N 0.1045(3) -0.0623(2) 0.59740(12) 0.0387(6) Uani 1 1 d . . . . .
N3 N 0.1942(3) 0.2085(2) 0.53846(13) 0.0462(7) Uani 1 1 d . . . . .
N4 N 0.2276(3) 0.2273(2) 0.47628(13) 0.0448(7) Uani 1 1 d . . . . .
N5 N 0.2471(3) 0.0018(2) 0.36518(12) 0.0382(6) Uani 1 1 d . . . . .
N6 N 0.2232(3) -0.0977(2) 0.38776(12) 0.0359(6) Uani 1 1 d . . . . .
C1 C 0.1068(4) -0.2351(3) 0.59166(18) 0.0510(9) Uani 1 1 d . U . . .
C2 C 0.0897(5) -0.2123(4) 0.65454(19) 0.0611(10) Uani 1 1 d . U . . .
H2 H 0.0800 -0.2606 0.6889 0.073 Uiso 1 1 calc R . . . .
C3 C 0.0902(4) -0.1044(3) 0.65556(16) 0.0494(8) Uani 1 1 d . U . . .
C4 C 0.1269(5) -0.3404(3) 0.5621(2) 0.0667(11) Uani 1 1 d . U . . .
C5 C 0.0845(5) -0.0349(4) 0.71123(18) 0.0641(11) Uani 1 1 d . U . . .
C6 C 0.2335(6) 0.2921(3) 0.5688(2) 0.0644(11) Uani 1 1 d . U . . .
C7 C 0.2930(6) 0.3670(3) 0.5280(2) 0.0767(14) Uani 1 1 d . U . . .
H7 H 0.3289 0.4332 0.5373 0.092 Uiso 1 1 calc R . . . .
C8 C 0.2874(5) 0.3223(3) 0.4702(2) 0.0624(11) Uani 1 1 d . U . . .
C9 C 0.2222(8) 0.2950(4) 0.6383(2) 0.0829(14) Uani 1 1 d . U . . .
C10 C 0.3394(8) 0.3669(4) 0.4084(3) 0.0890(16) Uani 1 1 d . U . . .
C11 C 0.3105(4) -0.0074(3) 0.30668(16) 0.0490(8) Uani 1 1 d . U . . .
C12 C 0.3281(4) -0.1130(3) 0.29038(16) 0.0546(9) Uani 1 1 d . U . . .
H12 H 0.3689 -0.1418 0.2520 0.066 Uiso 1 1 calc R . . . .
C13 C 0.2729(4) -0.1666(3) 0.34264(16) 0.0450(8) Uani 1 1 d . U . . .
C14 C 0.3569(6) 0.0871(4) 0.26935(19) 0.0685(12) Uani 1 1 d . U . . .
C15 C 0.2708(5) -0.2832(3) 0.3545(2) 0.0572(10) Uani 1 1 d . U . . .
Cu4 Cu 0.15537(4) 0.39826(3) 1.04870(2) 0.03382(10) Uani 1 1 d . . . . .
Cu5 Cu 0.13454(4) 0.64009(3) 0.99652(2) 0.03346(10) Uani 1 1 d . . . . .
Cu6 Cu 0.22676(4) 0.44999(3) 0.90184(2) 0.03414(10) Uani 1 1 d . . . . .
F19 F 0.0438(3) 0.3370(2) 1.18887(14) 0.0799(8) Uani 1 1 d . U . . .
F20 F 0.0796(5) 0.4337(3) 1.26495(13) 0.1311(15) Uani 1 1 d . U . . .
F21 F 0.2497(3) 0.3771(3) 1.20136(17) 0.0979(11) Uani 1 1 d . U . . .
F22 F 0.0611(7) 0.8415(3) 1.17551(18) 0.183(3) Uani 1 1 d . U . . .
F23 F 0.2237(4) 0.8229(3) 1.1032(2) 0.1131(12) Uani 1 1 d . U . . .
F24 F 0.0161(4) 0.8311(2) 1.08204(19) 0.0977(10) Uani 1 1 d . U . . .
F25 F 0.0807(5) 0.8757(3) 0.9498(2) 0.1258(14) Uani 1 1 d . U . . .
F26 F 0.2953(4) 0.8767(2) 0.95658(15) 0.0954(10) Uani 1 1 d . U . . .
F27 F 0.2112(6) 0.9465(2) 0.87716(16) 0.1387(18) Uani 1 1 d . U . . .
F28 F 0.3452(6) 0.6182(4) 0.71279(15) 0.164(2) Uani 1 1 d . U . . .
F29 F 0.2558(6) 0.4910(4) 0.75748(19) 0.172(2) Uani 1 1 d . U . . .
F30 F 0.4538(5) 0.5187(4) 0.77101(19) 0.1417(18) Uani 1 1 d . U . . .
F31 F 0.4649(4) 0.2781(2) 0.81985(14) 0.0977(10) Uani 1 1 d . U . . .
F32 F 0.2518(5) 0.2614(4) 0.80407(14) 0.1253(15) Uani 1 1 d . U . . .
F33 F 0.3850(4) 0.1248(2) 0.81701(16) 0.1125(13) Uani 1 1 d . U . . .
F34 F 0.347(2) 0.0495(7) 1.0692(5) 0.099(4) Uani 0.50(2) 1 d . U P B 2
F35 F 0.1669(14) 0.1440(19) 1.1010(8) 0.131(6) Uani 0.50(2) 1 d . U P B 2
F36 F 0.362(2) 0.2017(7) 1.1045(6) 0.105(4) Uani 0.50(2) 1 d . U P B 2
N7 N 0.1104(3) 0.5098(2) 1.10425(11) 0.0343(5) Uani 1 1 d . . . . .
N8 N 0.1041(3) 0.6117(2) 1.08212(11) 0.0346(5) Uani 1 1 d . . . . .
N9 N 0.1907(3) 0.6705(2) 0.91283(12) 0.0360(6) Uani 1 1 d . . . . .
N10 N 0.2283(3) 0.5905(2) 0.87264(11) 0.0357(6) Uani 1 1 d . . . . .
N11 N 0.2457(3) 0.3108(2) 0.93192(13) 0.0396(6) Uani 1 1 d . . . . .
N12 N 0.2228(3) 0.2896(2) 0.99450(13) 0.0403(6) Uani 1 1 d . . . . .
C16 C 0.1026(4) 0.5140(3) 1.16699(15) 0.0463(8) Uani 1 1 d . U . . .
C17 C 0.0905(5) 0.6174(4) 1.18643(17) 0.0594(10) Uani 1 1 d . U . . .
H17 H 0.0822 0.6425 1.2280 0.071 Uiso 1 1 calc R . . . .
C18 C 0.0932(4) 0.6761(3) 1.13195(16) 0.0481(8) Uani 1 1 d . U . . .
C19 C 0.1183(5) 0.4156(4) 1.20560(18) 0.0614(11) Uani 1 1 d . U . . .
C20 C 0.0957(6) 0.7933(4) 1.1237(2) 0.0687(12) Uani 1 1 d . U . . .
C21 C 0.2248(4) 0.7625(3) 0.88259(17) 0.0477(8) Uani 1 1 d . U . . .
C22 C 0.2855(5) 0.7429(3) 0.82287(18) 0.0588(10) Uani 1 1 d . U . . .
H22 H 0.3198 0.7925 0.7919 0.071 Uiso 1 1 calc R . . . .
C23 C 0.2845(4) 0.6347(3) 0.81888(16) 0.0483(8) Uani 1 1 d . U . . .
C24 C 0.2041(6) 0.8654(3) 0.9150(2) 0.0687(12) Uani 1 1 d . U . . .
C25 C 0.3371(5) 0.5671(4) 0.76477(19) 0.0668(11) Uani 1 1 d . U . . .
C26 C 0.3124(4) 0.2238(3) 0.90572(19) 0.0529(9) Uani 1 1 d . U . . .
C27 C 0.3349(5) 0.1462(3) 0.9489(2) 0.0626(10) Uani 1 1 d . U . . .
H27 H 0.3793 0.0778 0.9424 0.075 Uiso 1 1 calc R . . . .
C28 C 0.2773(4) 0.1908(3) 1.00461(19) 0.0528(9) Uani 1 1 d . U . . .
C29 C 0.3515(6) 0.2216(4) 0.8366(2) 0.0731(13) Uani 1 1 d . U . . .
C30 C 0.2802(7) 0.1454(4) 1.0687(2) 0.0730(12) Uani 1 1 d . U . . .
C31 C 0.5249(6) -0.0390(7) 0.4405(3) 0.102(2) Uani 1 1 d . U . . .
H31 H 0.5420 -0.0661 0.3995 0.122 Uiso 1 1 calc R . . . .
C32 C 0.5444(5) 0.0674(6) 0.4511(3) 0.0965(18) Uani 1 1 d . U . . .
H32 H 0.5748 0.1134 0.4175 0.116 Uiso 1 1 calc R . . . .
C33 C 0.5192(6) 0.1052(6) 0.5105(4) 0.101(2) Uani 1 1 d . U . . .
H33 H 0.5323 0.1779 0.5180 0.121 Uiso 1 1 calc R . . . .
C34 C 0.4895(5) 0.4299(6) 1.0492(3) 0.0873(17) Uani 1 1 d . U . . .
H34 H 0.4818 0.3815 1.0836 0.105 Uiso 1 1 calc R . . . .
C35 C 0.5331(5) 0.3933(5) 0.9912(3) 0.0882(16) Uani 1 1 d . U . . .
H35 H 0.5562 0.3200 0.9850 0.106 Uiso 1 1 calc R . . . .
C36 C 0.5434(5) 0.4645(6) 0.9410(3) 0.0900(17) Uani 1 1 d . U . . .
H36 H 0.5731 0.4401 0.9002 0.108 Uiso 1 1 calc R . . . .
F7A F 0.3223(12) 0.2816(18) 0.6647(4) 0.160(6) Uani 0.513(6) 1 d . U P A 2
F9A F 0.1410(11) 0.3812(6) 0.6629(3) 0.097(3) Uani 0.513(6) 1 d . U P A 2
F8A F 0.1164(13) 0.2196(6) 0.6664(3) 0.118(4) Uani 0.487(6) 1 d . U P A 2
F34A F 0.3958(15) 0.155(2) 1.0888(9) 0.155(7) Uani 0.50(2) 1 d . U P B 1
F35A F 0.239(2) 0.0457(6) 1.0709(5) 0.118(5) Uani 0.50(2) 1 d . U P B 1
F36A F 0.1746(17) 0.1919(8) 1.1080(6) 0.099(3) Uani 0.50(2) 1 d . U P B 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cu2 3.0309(11) 2_556 ?
Cu1 N1 1.872(3) . ?
Cu1 N6 1.870(3) . ?
Cu2 Cu1 3.0310(11) 2_556 ?
Cu2 N2 1.866(3) . ?
Cu2 N3 1.871(3) . ?
Cu3 N4 1.871(3) . ?
Cu3 N5 1.874(3) . ?
F1 C4 1.336(5) . ?
F2 C4 1.326(6) . ?
F3 C4 1.314(5) . ?
F4 C5 1.332(5) . ?
F5 C5 1.310(5) . ?
F6 C5 1.332(5) . ?
F7 C9 1.445(10) . ?
F8 C9 1.354(11) . ?
F9 C9 1.084(10) . ?
F10 C10 1.266(7) . ?
F11 C10 1.325(8) . ?
F12 C10 1.229(8) . ?
F13 C14 1.320(5) . ?
F14 C14 1.334(6) . ?
F15 C14 1.308(5) . ?
F16 C15 1.304(5) . ?
F17 C15 1.304(5) . ?
F18 C15 1.298(5) . ?
N1 N2 1.363(4) . ?
N1 C1 1.351(4) . ?
N2 C3 1.349(4) . ?
N3 N4 1.365(4) . ?
N3 C6 1.340(5) . ?
N4 C8 1.350(5) . ?
N5 N6 1.358(4) . ?
N5 C11 1.347(4) . ?
N6 C13 1.353(4) . ?
C1 C2 1.382(6) . ?
C1 C4 1.482(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.363(6) . ?
C3 C5 1.495(6) . ?
C6 C7 1.381(7) . ?
C6 C9 1.491(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(6) . ?
C8 C10 1.485(7) . ?
C9 F7A 1.166(11) . ?
C9 F9A 1.389(9) . ?
C9 F8A 1.495(11) . ?
C11 C12 1.384(6) . ?
C11 C14 1.485(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.374(5) . ?
C13 C15 1.489(6) . ?
Cu4 N7 1.872(3) . ?
Cu4 N12 1.868(3) . ?
Cu5 N8 1.868(3) . ?
Cu5 N9 1.867(3) . ?
Cu6 N10 1.871(3) . ?
Cu6 N11 1.868(3) . ?
F19 C19 1.323(5) . ?
F20 C19 1.316(5) . ?
F21 C19 1.322(6) . ?
F22 C20 1.288(5) . ?
F23 C20 1.326(6) . ?
F24 C20 1.304(6) . ?
F25 C24 1.335(7) . ?
F26 C24 1.326(5) . ?
F27 C24 1.296(5) . ?
F28 C25 1.279(5) . ?
F29 C25 1.283(6) . ?
F30 C25 1.265(6) . ?
F31 C29 1.339(6) . ?
F32 C29 1.317(6) . ?
F33 C29 1.316(5) . ?
F34 C30 1.345(9) . ?
F35 C30 1.227(14) . ?
F36 C30 1.378(13) . ?
N7 N8 1.363(4) . ?
N7 C16 1.348(4) . ?
N8 C18 1.352(4) . ?
N9 N10 1.355(4) . ?
N9 C21 1.357(4) . ?
N10 C23 1.348(4) . ?
N11 N12 1.368(4) . ?
N11 C26 1.349(5) . ?
N12 C28 1.352(5) . ?
C16 C17 1.375(6) . ?
C16 C19 1.491(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.375(6) . ?
C18 C20 1.488(6) . ?
C21 C22 1.379(6) . ?
C21 C24 1.482(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.370(6) . ?
C23 C25 1.491(6) . ?
C26 C27 1.363(6) . ?
C26 C29 1.498(6) . ?
C27 H27 0.9500 . ?
C27 C28 1.387(6) . ?
C28 C30 1.488(6) . ?
C30 F34A 1.238(14) . ?
C30 F35A 1.333(10) . ?
C30 F36A 1.368(14) . ?
C31 H31 0.9500 . ?
C31 C32 1.390(10) . ?
C31 C33 1.379(10) 2_656 ?
C32 H32 0.9500 . ?
C32 C33 1.369(9) . ?
C33 C31 1.378(10) 2_656 ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C34 C35 1.360(9) . ?
C34 C36 1.371(9) 2_667 ?
C35 H35 0.9500 . ?
C35 C36 1.391(9) . ?
C36 C34 1.371(9) 2_667 ?
C36 H36 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 Cu2 100.16(9) . 2_556 ?
N6 Cu1 Cu2 87.06(8) . 2_556 ?
N6 Cu1 N1 172.78(12) . . ?
N2 Cu2 Cu1 95.88(9) . 2_556 ?
N2 Cu2 N3 172.16(13) . . ?
N3 Cu2 Cu1 91.92(10) . 2_556 ?
N4 Cu3 N5 174.24(13) . . ?
N2 N1 Cu1 120.0(2) . . ?
C1 N1 Cu1 132.2(3) . . ?
C1 N1 N2 107.3(3) . . ?
N1 N2 Cu2 119.6(2) . . ?
C3 N2 Cu2 132.7(3) . . ?
C3 N2 N1 107.0(3) . . ?
N4 N3 Cu2 120.3(2) . . ?
C6 N3 Cu2 131.6(3) . . ?
C6 N3 N4 107.2(3) . . ?
N3 N4 Cu3 119.7(2) . . ?
C8 N4 Cu3 130.9(3) . . ?
C8 N4 N3 107.4(3) . . ?
N6 N5 Cu3 119.42(19) . . ?
C11 N5 Cu3 131.4(3) . . ?
C11 N5 N6 107.6(3) . . ?
N5 N6 Cu1 120.54(19) . . ?
C13 N6 Cu1 131.3(2) . . ?
C13 N6 N5 107.5(3) . . ?
N1 C1 C2 110.5(4) . . ?
N1 C1 C4 121.1(3) . . ?
C2 C1 C4 128.2(4) . . ?
C1 C2 H2 128.1 . . ?
C3 C2 C1 103.7(3) . . ?
C3 C2 H2 128.1 . . ?
N2 C3 C2 111.5(3) . . ?
N2 C3 C5 120.6(4) . . ?
C2 C3 C5 127.9(4) . . ?
F1 C4 C1 112.2(4) . . ?
F2 C4 F1 103.6(4) . . ?
F2 C4 C1 113.6(4) . . ?
F3 C4 F1 107.8(4) . . ?
F3 C4 F2 106.5(5) . . ?
F3 C4 C1 112.5(4) . . ?
F4 C5 F6 106.8(4) . . ?
F4 C5 C3 111.0(4) . . ?
F5 C5 F4 107.6(4) . . ?
F5 C5 F6 106.3(4) . . ?
F5 C5 C3 113.3(3) . . ?
F6 C5 C3 111.5(4) . . ?
N3 C6 C7 111.4(4) . . ?
N3 C6 C9 121.8(4) . . ?
C7 C6 C9 126.5(4) . . ?
C6 C7 H7 128.4 . . ?
C6 C7 C8 103.2(4) . . ?
C8 C7 H7 128.4 . . ?
N4 C8 C7 110.7(4) . . ?
N4 C8 C10 121.9(4) . . ?
C7 C8 C10 127.4(4) . . ?
F7 C9 C6 105.3(6) . . ?
F8 C9 F7 98.2(8) . . ?
F8 C9 C6 109.4(5) . . ?
F9 C9 F7 112.3(10) . . ?
F9 C9 F8 114.1(11) . . ?
F9 C9 C6 115.8(7) . . ?
C6 C9 F8A 110.9(5) . . ?
F7A C9 C6 120.4(8) . . ?
F7A C9 F9A 110.1(10) . . ?
F7A C9 F8A 106.9(12) . . ?
F9A C9 C6 113.3(6) . . ?
F9A C9 F8A 91.2(7) . . ?
F10 C10 F11 101.1(6) . . ?
F10 C10 C8 114.7(5) . . ?
F11 C10 C8 111.4(5) . . ?
F12 C10 F10 112.0(6) . . ?
F12 C10 F11 101.9(6) . . ?
F12 C10 C8 114.1(6) . . ?
N5 C11 C12 110.5(3) . . ?
N5 C11 C14 121.4(3) . . ?
C12 C11 C14 128.1(3) . . ?
C11 C12 H12 128.0 . . ?
C13 C12 C11 103.9(3) . . ?
C13 C12 H12 128.0 . . ?
N6 C13 C12 110.5(3) . . ?
N6 C13 C15 120.7(3) . . ?
C12 C13 C15 128.7(3) . . ?
F13 C14 F14 104.9(5) . . ?
F13 C14 C11 112.2(4) . . ?
F14 C14 C11 112.8(4) . . ?
F15 C14 F13 108.0(4) . . ?
F15 C14 F14 107.1(5) . . ?
F15 C14 C11 111.4(4) . . ?
F16 C15 C13 112.5(3) . . ?
F17 C15 F16 107.0(4) . . ?
F17 C15 C13 112.1(4) . . ?
F18 C15 F16 104.4(4) . . ?
F18 C15 F17 107.1(4) . . ?
F18 C15 C13 113.2(3) . . ?
N12 Cu4 N7 173.12(12) . . ?
N9 Cu5 N8 172.15(12) . . ?
N11 Cu6 N10 173.84(12) . . ?
N8 N7 Cu4 119.73(19) . . ?
C16 N7 Cu4 132.0(3) . . ?
C16 N7 N8 107.4(3) . . ?
N7 N8 Cu5 120.36(19) . . ?
C18 N8 Cu5 131.7(2) . . ?
C18 N8 N7 107.3(3) . . ?
N10 N9 Cu5 120.0(2) . . ?
N10 N9 C21 107.2(3) . . ?
C21 N9 Cu5 131.9(2) . . ?
N9 N10 Cu6 119.64(19) . . ?
C23 N10 Cu6 132.0(3) . . ?
C23 N10 N9 107.3(3) . . ?
N12 N11 Cu6 120.1(2) . . ?
C26 N11 Cu6 131.1(3) . . ?
C26 N11 N12 106.7(3) . . ?
N11 N12 Cu4 119.5(2) . . ?
C28 N12 Cu4 132.3(3) . . ?
C28 N12 N11 107.4(3) . . ?
N7 C16 C17 110.7(3) . . ?
N7 C16 C19 121.0(4) . . ?
C17 C16 C19 128.1(3) . . ?
C16 C17 H17 127.9 . . ?
C16 C17 C18 104.1(3) . . ?
C18 C17 H17 127.9 . . ?
N8 C18 C17 110.5(3) . . ?
N8 C18 C20 121.0(3) . . ?
C17 C18 C20 128.3(3) . . ?
F19 C19 C16 113.4(3) . . ?
F20 C19 F19 107.4(4) . . ?
F20 C19 F21 107.3(4) . . ?
F20 C19 C16 111.2(4) . . ?
F21 C19 F19 105.0(4) . . ?
F21 C19 C16 112.1(3) . . ?
F22 C20 F23 106.6(5) . . ?
F22 C20 F24 108.9(5) . . ?
F22 C20 C18 111.8(4) . . ?
F23 C20 C18 111.0(4) . . ?
F24 C20 F23 104.4(4) . . ?
F24 C20 C18 113.7(4) . . ?
N9 C21 C22 110.7(3) . . ?
N9 C21 C24 120.9(3) . . ?
C22 C21 C24 128.4(3) . . ?
C21 C22 H22 128.3 . . ?
C23 C22 C21 103.4(3) . . ?
C23 C22 H22 128.3 . . ?
N10 C23 C22 111.4(3) . . ?
N10 C23 C25 120.5(4) . . ?
C22 C23 C25 128.1(3) . . ?
F25 C24 C21 113.1(4) . . ?
F26 C24 F25 102.4(4) . . ?
F26 C24 C21 112.6(4) . . ?
F27 C24 F25 106.6(5) . . ?
F27 C24 F26 108.2(4) . . ?
F27 C24 C21 113.1(4) . . ?
F28 C25 F29 104.9(5) . . ?
F28 C25 C23 113.0(4) . . ?
F29 C25 C23 112.3(4) . . ?
F30 C25 F28 109.4(5) . . ?
F30 C25 F29 102.7(6) . . ?
F30 C25 C23 113.6(4) . . ?
N11 C26 C27 112.0(4) . . ?
N11 C26 C29 119.8(4) . . ?
C27 C26 C29 128.3(4) . . ?
C26 C27 H27 128.3 . . ?
C26 C27 C28 103.4(4) . . ?
C28 C27 H27 128.3 . . ?
N12 C28 C27 110.6(4) . . ?
N12 C28 C30 121.5(4) . . ?
C27 C28 C30 127.7(4) . . ?
F31 C29 C26 111.6(4) . . ?
F32 C29 F31 105.9(5) . . ?
F32 C29 C26 113.5(4) . . ?
F33 C29 F31 105.7(4) . . ?
F33 C29 F32 107.9(5) . . ?
F33 C29 C26 111.8(4) . . ?
F34 C30 F36 100.5(8) . . ?
F34 C30 C28 112.4(6) . . ?
F35 C30 F34 110.6(8) . . ?
F35 C30 F36 103.0(11) . . ?
F35 C30 C28 116.4(8) . . ?
F36 C30 C28 112.4(6) . . ?
F34A C30 C28 111.8(8) . . ?
F34A C30 F35A 113.1(9) . . ?
F34A C30 F36A 110.7(13) . . ?
F35A C30 C28 110.5(7) . . ?
F35A C30 F36A 99.9(9) . . ?
F36A C30 C28 110.1(6) . . ?
C32 C31 H31 120.0 . . ?
C33 C31 H31 120.0 2_656 . ?
C33 C31 C32 120.0(7) 2_656 . ?
C31 C32 H32 120.4 . . ?
C33 C32 C31 119.3(7) . . ?
C33 C32 H32 120.4 . . ?
C31 C33 H33 119.6 2_656 . ?
C32 C33 C31 120.7(7) . 2_656 ?
C32 C33 H33 119.6 . . ?
C35 C34 H34 119.4 . . ?
C35 C34 C36 121.1(6) . 2_667 ?
C36 C34 H34 119.4 2_667 . ?
C34 C35 H35 120.4 . . ?
C34 C35 C36 119.2(6) . . ?
C36 C35 H35 120.4 . . ?
C34 C36 C35 119.7(6) 2_667 . ?
C34 C36 H36 120.2 2_667 . ?
C35 C36 H36 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 Cu2 N2 N1 82.8(2) 2_556 . . . ?
Cu1 Cu2 N2 C3 -108.1(3) 2_556 . . . ?
Cu1 Cu2 N3 N4 -78.2(3) 2_556 . . . ?
Cu1 Cu2 N3 C6 114.5(4) 2_556 . . . ?
Cu1 N1 N2 Cu2 -1.1(3) . . . . ?
Cu1 N1 N2 C3 -172.8(2) . . . . ?
Cu1 N1 C1 C2 172.0(3) . . . . ?
Cu1 N1 C1 C4 -3.4(6) . . . . ?
Cu1 N6 C13 C12 -171.4(3) . . . . ?
Cu1 N6 C13 C15 5.1(5) . . . . ?
Cu2 Cu1 N1 N2 -88.0(2) 2_556 . . . ?
Cu2 Cu1 N1 C1 101.7(3) 2_556 . . . ?
Cu2 Cu1 N6 N5 85.1(2) 2_556 . . . ?
Cu2 Cu1 N6 C13 -105.0(3) 2_556 . . . ?
Cu2 N2 C3 C2 -170.5(3) . . . . ?
Cu2 N2 C3 C5 6.4(5) . . . . ?
Cu2 N3 N4 Cu3 -4.3(4) . . . . ?
Cu2 N3 N4 C8 -169.8(3) . . . . ?
Cu2 N3 C6 C7 168.5(3) . . . . ?
Cu2 N3 C6 C9 -6.9(7) . . . . ?
Cu3 N4 C8 C7 -163.7(3) . . . . ?
Cu3 N4 C8 C10 15.6(7) . . . . ?
Cu3 N5 N6 Cu1 5.1(3) . . . . ?
Cu3 N5 N6 C13 -166.9(2) . . . . ?
Cu3 N5 C11 C12 165.2(3) . . . . ?
Cu3 N5 C11 C14 -12.4(6) . . . . ?
N1 N2 C3 C2 -0.4(4) . . . . ?
N1 N2 C3 C5 176.5(3) . . . . ?
N1 C1 C2 C3 -1.0(5) . . . . ?
N1 C1 C4 F1 72.2(5) . . . . ?
N1 C1 C4 F2 -44.9(6) . . . . ?
N1 C1 C4 F3 -166.0(4) . . . . ?
N2 N1 C1 C2 0.8(4) . . . . ?
N2 N1 C1 C4 -174.6(4) . . . . ?
N2 C3 C5 F4 159.5(4) . . . . ?
N2 C3 C5 F5 38.4(6) . . . . ?
N2 C3 C5 F6 -81.6(5) . . . . ?
N3 N4 C8 C7 -0.4(5) . . . . ?
N3 N4 C8 C10 178.9(5) . . . . ?
N3 C6 C7 C8 -0.3(6) . . . . ?
N3 C6 C9 F7 162.7(7) . . . . ?
N3 C6 C9 F8 58.1(10) . . . . ?
N3 C6 C9 F9 -72.7(13) . . . . ?
N3 C6 C9 F7A 103.8(16) . . . . ?
N3 C6 C9 F9A -122.9(7) . . . . ?
N3 C6 C9 F8A -22.0(9) . . . . ?
N4 N3 C6 C7 0.0(5) . . . . ?
N4 N3 C6 C9 -175.4(5) . . . . ?
N4 C8 C10 F10 -173.8(6) . . . . ?
N4 C8 C10 F11 -59.7(8) . . . . ?
N4 C8 C10 F12 55.1(8) . . . . ?
N5 N6 C13 C12 -0.5(4) . . . . ?
N5 N6 C13 C15 176.0(3) . . . . ?
N5 C11 C12 C13 -0.6(5) . . . . ?
N5 C11 C14 F13 -45.2(6) . . . . ?
N5 C11 C14 F14 73.1(5) . . . . ?
N5 C11 C14 F15 -166.4(4) . . . . ?
N6 N5 C11 C12 0.2(4) . . . . ?
N6 N5 C11 C14 -177.4(4) . . . . ?
N6 C13 C15 F16 -66.6(5) . . . . ?
N6 C13 C15 F17 172.8(4) . . . . ?
N6 C13 C15 F18 51.5(6) . . . . ?
C1 N1 N2 Cu2 171.4(2) . . . . ?
C1 N1 N2 C3 -0.3(4) . . . . ?
C1 C2 C3 N2 0.9(5) . . . . ?
C1 C2 C3 C5 -175.7(4) . . . . ?
C2 C1 C4 F1 -102.4(5) . . . . ?
C2 C1 C4 F2 140.5(5) . . . . ?
C2 C1 C4 F3 19.4(7) . . . . ?
C2 C3 C5 F4 -24.2(6) . . . . ?
C2 C3 C5 F5 -145.3(4) . . . . ?
C2 C3 C5 F6 94.7(5) . . . . ?
C4 C1 C2 C3 174.0(4) . . . . ?
C6 N3 N4 Cu3 165.7(3) . . . . ?
C6 N3 N4 C8 0.3(4) . . . . ?
C6 C7 C8 N4 0.4(6) . . . . ?
C6 C7 C8 C10 -178.9(6) . . . . ?
C7 C6 C9 F7 -12.0(10) . . . . ?
C7 C6 C9 F8 -116.6(8) . . . . ?
C7 C6 C9 F9 112.7(13) . . . . ?
C7 C6 C9 F7A -70.9(16) . . . . ?
C7 C6 C9 F9A 62.4(10) . . . . ?
C7 C6 C9 F8A 163.3(7) . . . . ?
C7 C8 C10 F10 5.5(10) . . . . ?
C7 C8 C10 F11 119.5(7) . . . . ?
C7 C8 C10 F12 -125.7(7) . . . . ?
C9 C6 C7 C8 174.9(5) . . . . ?
C11 N5 N6 Cu1 172.2(2) . . . . ?
C11 N5 N6 C13 0.2(4) . . . . ?
C11 C12 C13 N6 0.7(4) . . . . ?
C11 C12 C13 C15 -175.5(4) . . . . ?
C12 C11 C14 F13 137.6(5) . . . . ?
C12 C11 C14 F14 -104.1(5) . . . . ?
C12 C11 C14 F15 16.4(7) . . . . ?
C12 C13 C15 F16 109.2(5) . . . . ?
C12 C13 C15 F17 -11.4(6) . . . . ?
C12 C13 C15 F18 -132.7(5) . . . . ?
C14 C11 C12 C13 176.9(4) . . . . ?
Cu4 N7 N8 Cu5 1.9(3) . . . . ?
Cu4 N7 N8 C18 -170.1(2) . . . . ?
Cu4 N7 C16 C17 169.0(3) . . . . ?
Cu4 N7 C16 C19 -6.3(5) . . . . ?
Cu4 N12 C28 C27 -169.7(3) . . . . ?
Cu4 N12 C28 C30 6.2(6) . . . . ?
Cu5 N8 C18 C17 -171.5(3) . . . . ?
Cu5 N8 C18 C20 4.3(6) . . . . ?
Cu5 N9 N10 Cu6 -1.1(3) . . . . ?
Cu5 N9 N10 C23 -170.5(2) . . . . ?
Cu5 N9 C21 C22 168.5(3) . . . . ?
Cu5 N9 C21 C24 -7.8(6) . . . . ?
Cu6 N10 C23 C22 -167.1(3) . . . . ?
Cu6 N10 C23 C25 12.3(6) . . . . ?
Cu6 N11 N12 Cu4 6.0(3) . . . . ?
Cu6 N11 N12 C28 -164.7(2) . . . . ?
Cu6 N11 C26 C27 162.7(3) . . . . ?
Cu6 N11 C26 C29 -17.5(6) . . . . ?
N7 N8 C18 C17 -0.8(4) . . . . ?
N7 N8 C18 C20 175.0(4) . . . . ?
N7 C16 C17 C18 -0.7(4) . . . . ?
N7 C16 C19 F19 -46.2(5) . . . . ?
N7 C16 C19 F20 -167.4(4) . . . . ?
N7 C16 C19 F21 72.6(5) . . . . ?
N8 N7 C16 C17 0.3(4) . . . . ?
N8 N7 C16 C19 -175.0(3) . . . . ?
N8 C18 C20 F22 169.4(5) . . . . ?
N8 C18 C20 F23 -71.8(5) . . . . ?
N8 C18 C20 F24 45.5(6) . . . . ?
N9 N10 C23 C22 0.4(4) . . . . ?
N9 N10 C23 C25 179.8(4) . . . . ?
N9 C21 C22 C23 0.6(5) . . . . ?
N9 C21 C24 F25 -44.0(6) . . . . ?
N9 C21 C24 F26 71.5(6) . . . . ?
N9 C21 C24 F27 -165.4(4) . . . . ?
N10 N9 C21 C22 -0.4(4) . . . . ?
N10 N9 C21 C24 -176.7(4) . . . . ?
N10 C23 C25 F28 159.2(5) . . . . ?
N10 C23 C25 F29 40.7(7) . . . . ?
N10 C23 C25 F30 -75.4(6) . . . . ?
N11 N12 C28 C27 -0.6(4) . . . . ?
N11 N12 C28 C30 175.3(4) . . . . ?
N11 C26 C27 C28 0.0(5) . . . . ?
N11 C26 C29 F31 76.7(6) . . . . ?
N11 C26 C29 F32 -42.9(6) . . . . ?
N11 C26 C29 F33 -165.2(4) . . . . ?
N12 N11 C26 C27 -0.3(4) . . . . ?
N12 N11 C26 C29 179.5(4) . . . . ?
N12 C28 C30 F34 -175.6(9) . . . . ?
N12 C28 C30 F35 55.4(15) . . . . ?
N12 C28 C30 F36 -63.0(10) . . . . ?
N12 C28 C30 F34A -97.6(16) . . . . ?
N12 C28 C30 F35A 135.4(11) . . . . ?
N12 C28 C30 F36A 26.0(9) . . . . ?
C16 N7 N8 Cu5 172.3(2) . . . . ?
C16 N7 N8 C18 0.3(3) . . . . ?
C16 C17 C18 N8 0.9(5) . . . . ?
C16 C17 C18 C20 -174.5(4) . . . . ?
C17 C16 C19 F19 139.4(4) . . . . ?
C17 C16 C19 F20 18.3(6) . . . . ?
C17 C16 C19 F21 -101.8(5) . . . . ?
C17 C18 C20 F22 -15.7(8) . . . . ?
C17 C18 C20 F23 103.1(5) . . . . ?
C17 C18 C20 F24 -139.6(5) . . . . ?
C19 C16 C17 C18 174.1(4) . . . . ?
C21 N9 N10 Cu6 169.4(2) . . . . ?
C21 N9 N10 C23 0.0(4) . . . . ?
C21 C22 C23 N10 -0.6(5) . . . . ?
C21 C22 C23 C25 -180.0(4) . . . . ?
C22 C21 C24 F25 140.5(5) . . . . ?
C22 C21 C24 F26 -104.0(5) . . . . ?
C22 C21 C24 F27 19.1(7) . . . . ?
C22 C23 C25 F28 -21.4(7) . . . . ?
C22 C23 C25 F29 -139.9(5) . . . . ?
C22 C23 C25 F30 104.0(6) . . . . ?
C24 C21 C22 C23 176.5(4) . . . . ?
C26 N11 N12 Cu4 171.3(2) . . . . ?
C26 N11 N12 C28 0.6(4) . . . . ?
C26 C27 C28 N12 0.4(5) . . . . ?
C26 C27 C28 C30 -175.2(4) . . . . ?
C27 C26 C29 F31 -103.6(5) . . . . ?
C27 C26 C29 F32 136.8(5) . . . . ?
C27 C26 C29 F33 14.5(8) . . . . ?
C27 C28 C30 F34 -0.4(11) . . . . ?
C27 C28 C30 F35 -129.4(14) . . . . ?
C27 C28 C30 F36 112.2(10) . . . . ?
C27 C28 C30 F34A 77.6(16) . . . . ?
C27 C28 C30 F35A -49.4(12) . . . . ?
C27 C28 C30 F36A -158.9(8) . . . . ?
C29 C26 C27 C28 -179.8(4) . . . . ?
C31 C32 C33 C31 0.0(8) . . . 2_656 ?
C33 C31 C32 C33 0.0(8) 2_656 . . . ?
C34 C35 C36 C34 0.4(7) . . . 2_667 ?
C36 C34 C35 C36 -0.4(7) 2_667 . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rad202_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1053392'
_audit_update_record             
;
2015-05-10 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_audit_creation_date             2015-03-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H3 Cu3 F18 N6, C9 H12'
_chemical_formula_sum            'C24 H15 Cu3 F18 N6'
_chemical_formula_weight         920.04
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   19.975(2)
_cell_length_b                   19.975(2)
_cell_length_c                   13.2744(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4586.8(11)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.598
_shelx_estimated_absorpt_T_min   0.465
_exptl_absorpt_coefficient_mu    2.207
_exptl_absorpt_correction_T_max  0.9029
_exptl_absorpt_correction_T_min  0.7449
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.998
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2700
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36711
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         40.268
_diffrn_reflns_theta_min         3.474
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Quest CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.968
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                5699
_reflns_number_total             6277
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 2575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         6277
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0330P)²+1.4054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0659
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.36546(2) 0.59489(2) 0.44746(2) 0.01890(4) Uani 1 1 d . . . . .
F1 F 0.30852(16) 0.42304(16) 0.57809(16) 0.0696(7) Uani 1 1 d . . . . .
F2 F 0.23200(10) 0.32432(9) 0.4906(2) 0.0597(6) Uani 1 1 d . . . . .
F3 F 0.33312(11) 0.41712(13) 0.42519(17) 0.0574(5) Uani 1 1 d . . . . .
F4 F 0.00658(8) 0.39413(9) 0.4017(2) 0.0577(5) Uani 1 1 d . . . . .
F5 F 0.07039(12) 0.48717(19) 0.29984(16) 0.0751(8) Uani 1 1 d . . . . .
F6 F 0.05333(12) 0.51007(14) 0.4504(2) 0.0643(6) Uani 1 1 d . . . . .
N1 N 0.26278(8) 0.51507(7) 0.45645(10) 0.0180(2) Uani 1 1 d . . . . .
N2 N 0.20664(8) 0.53196(7) 0.43416(10) 0.0173(2) Uani 1 1 d . . . . .
C1 C 0.22944(9) 0.43750(9) 0.46059(13) 0.0207(2) Uani 1 1 d . . . . .
C2 C 0.15092(10) 0.40257(9) 0.44047(14) 0.0223(3) Uani 1 1 d . . . . .
H2 H 0.1138 0.3490 0.4386 0.027 Uiso 1 1 calc R . . . .
C3 C 0.13980(9) 0.46469(9) 0.42381(12) 0.0193(2) Uani 1 1 d . . . . .
C4 C 0.27515(11) 0.40011(11) 0.48902(18) 0.0291(3) Uani 1 1 d . . . . .
C5 C 0.06734(10) 0.46387(11) 0.39375(16) 0.0273(3) Uani 1 1 d . . . . .
C6 C 0.40898(11) 0.67912(12) 0.69613(13) 0.0247(3) Uani 1 1 d . . . . .
C7 C 0.34548(12) 0.60425(10) 0.69595(14) 0.0253(3) Uani 1 1 d . . . . .
H7 H 0.3539 0.5614 0.6957 0.030 Uiso 1 1 calc R . . . .
C8 C 0.49037(14) 0.69250(17) 0.69884(16) 0.0366(5) Uani 1 1 d . . . . .
H8A H 0.5034 0.6801 0.6329 0.055 Uiso 1 1 calc GR . . . .
H8B H 0.4940 0.6593 0.7504 0.055 Uiso 1 1 calc GR . . . .
H8C H 0.5265 0.7468 0.7150 0.055 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu N1 1.8689(13) . ?
Cu N2 1.8720(13) 2_665 ?
F1 C4 1.322(3) . ?
F2 C4 1.315(2) . ?
F3 C4 1.335(3) . ?
F4 C5 1.317(2) . ?
F5 C5 1.321(3) . ?
F6 C5 1.324(3) . ?
N1 N2 1.3554(19) . ?
N1 C1 1.347(2) . ?
N2 Cu 1.8720(13) 3_565 ?
N2 C3 1.346(2) . ?
C1 C2 1.387(2) . ?
C1 C4 1.489(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(2) . ?
C3 C5 1.494(2) . ?
C6 C7 1.392(3) 2_665 ?
C6 C7 1.396(3) . ?
C6 C8 1.510(3) . ?
C7 C6 1.392(3) 3_565 ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu N2 178.25(6) . 2_665 ?
N2 N1 Cu 117.73(10) . . ?
C1 N1 Cu 133.18(12) . . ?
C1 N1 N2 107.48(13) . . ?
N1 N2 Cu 118.24(10) . 3_565 ?
C3 N2 Cu 132.77(11) . 3_565 ?
C3 N2 N1 107.75(13) . . ?
N1 C1 C2 110.80(14) . . ?
N1 C1 C4 120.86(15) . . ?
C2 C1 C4 128.27(15) . . ?
C1 C2 H2 128.4 . . ?
C3 C2 C1 103.17(13) . . ?
C3 C2 H2 128.4 . . ?
N2 C3 C2 110.79(14) . . ?
N2 C3 C5 120.68(14) . . ?
C2 C3 C5 128.48(15) . . ?
F1 C4 F3 104.9(2) . . ?
F1 C4 C1 112.49(17) . . ?
F2 C4 F1 108.2(2) . . ?
F2 C4 F3 106.8(2) . . ?
F2 C4 C1 111.61(16) . . ?
F3 C4 C1 112.51(18) . . ?
F4 C5 F5 107.7(2) . . ?
F4 C5 F6 106.7(2) . . ?
F4 C5 C3 111.46(16) . . ?
F5 C5 F6 106.2(2) . . ?
F5 C5 C3 112.00(16) . . ?
F6 C5 C3 112.45(17) . . ?
C7 C6 C7 118.64(18) 2_665 . ?
C7 C6 C8 120.6(2) 2_665 . ?
C7 C6 C8 120.71(19) . . ?
C6 C7 C6 121.36(18) 3_565 . ?
C6 C7 H7 119.3 . . ?
C6 C7 H7 119.3 3_565 . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
Cu N1 N2 Cu -24.33(15) . . . 3_565 ?
Cu N1 N2 C3 166.78(11) . . . . ?
Cu N1 C1 C2 -164.37(13) . . . . ?
Cu N1 C1 C4 18.6(3) . . . . ?
Cu N2 C3 C2 -165.86(12) 3_565 . . . ?
Cu N2 C3 C5 16.5(3) 3_565 . . . ?
N1 N2 C3 C2 0.77(19) . . . . ?
N1 N2 C3 C5 -176.83(15) . . . . ?
N1 C1 C2 C3 0.1(2) . . . . ?
N1 C1 C4 F1 57.0(3) . . . . ?
N1 C1 C4 F2 178.8(2) . . . . ?
N1 C1 C4 F3 -61.2(2) . . . . ?
N2 N1 C1 C2 0.32(19) . . . . ?
N2 N1 C1 C4 -176.75(17) . . . . ?
N2 C3 C5 F4 -170.96(19) . . . . ?
N2 C3 C5 F5 68.3(3) . . . . ?
N2 C3 C5 F6 -51.2(3) . . . . ?
C1 N1 N2 Cu 168.23(11) . . . 3_565 ?
C1 N1 N2 C3 -0.66(18) . . . . ?
C1 C2 C3 N2 -0.6(2) . . . . ?
C1 C2 C3 C5 176.81(18) . . . . ?
C2 C1 C4 F1 -119.5(2) . . . . ?
C2 C1 C4 F2 2.3(3) . . . . ?
C2 C1 C4 F3 122.3(2) . . . . ?
C2 C3 C5 F4 11.9(3) . . . . ?
C2 C3 C5 F5 -108.8(3) . . . . ?
C2 C3 C5 F6 131.7(2) . . . . ?
C4 C1 C2 C3 176.93(19) . . . . ?
C7 C6 C7 C6 -0.3(3) 2_665 . . 3_565 ?
C8 C6 C7 C6 178.30(13) . . . 3_565 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rad194_0m_a_final
_database_code_depnum_ccdc_archive 'CCDC 1053393'
_audit_update_record             
;
2015-05-10 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_audit_creation_date             2015-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H3 Cu3 F18 N6, 2(C5 H4)'
_chemical_formula_sum            'C25 H11 Cu3 F18 N6'
_chemical_formula_weight         928.02
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.7936(11)
_cell_length_b                   12.4534(11)
_cell_length_c                   12.7263(11)
_cell_angle_alpha                109.803(2)
_cell_angle_beta                 117.447(2)
_cell_angle_gamma                95.807(2)
_cell_volume                     1484.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      40.30
_cell_measurement_theta_min      3.14
_shelx_estimated_absorpt_T_max   0.732
_shelx_estimated_absorpt_T_min   0.393
_exptl_absorpt_coefficient_mu    2.274
_exptl_absorpt_correction_T_max  0.8377
_exptl_absorpt_correction_T_min  0.5966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0359 before and 0.0292 after correction.
The Ratio of minimum to maximum transmission is 0.7122.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.076
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.505
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.146
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16256
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         3.135
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6098
_reflns_number_total             6379
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         6379
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0223
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0292P)²+1.1218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0576
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C9-F7 = C9-F8 = C9-F9 = C9A-F7A = C9A-F8A = C9A-F9A
 1.335 with sigma of 0.005
 F7-F8 \\sim F8-F9 \\sim F9-F7
 with sigma of 0.01
 F7A-F8A \\sim F8A-F9A \\sim F9A-F7A
 with sigma of 0.01
 C9-C6 \\sim C9A-C6
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(F8A) \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F9A) \\sim Ueq, Uanis(F9)
\\sim Ueq, Uanis(F7A) \\sim Ueq, Uanis(F7) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.005
Uanis(C9) \\sim Ueq, Uanis(C9A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C9) = Uanis(C9A)
4. Others
 Sof(C9A)=Sof(F8A)=Sof(F7A)=Sof(F9A)=1-FVAR(1)
 Sof(C9)=Sof(F7)=Sof(F8)=Sof(F9)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C12(H12), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21),
 C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.55606(2) 0.24945(2) 0.78282(2) 0.01421(5) Uani 1 1 d . . . . .
Cu2 Cu 0.43957(2) 0.26865(2) 0.50887(2) 0.01596(5) Uani 1 1 d . . . . .
Cu3 Cu 0.24341(2) 0.22376(2) 0.60939(2) 0.01522(5) Uani 1 1 d . . . . .
F1 F 1.02389(9) 0.37648(9) 0.97470(10) 0.0250(2) Uani 1 1 d . . . . .
F2 F 0.87185(11) 0.21535(9) 0.90832(10) 0.0292(2) Uani 1 1 d . . . . .
F3 F 0.86834(10) 0.38764(9) 1.01907(9) 0.0251(2) Uani 1 1 d . . . . .
F4 F 0.82507(11) 0.47917(10) 0.55240(11) 0.0292(2) Uani 1 1 d . . . . .
F5 F 0.62450(12) 0.47778(11) 0.50653(12) 0.0350(3) Uani 1 1 d . . . . .
F6 F 0.65809(12) 0.31985(10) 0.40531(10) 0.0295(2) Uani 1 1 d . . . . .
F10 F -0.15103(13) 0.14314(12) 0.32615(16) 0.0503(4) Uani 1 1 d . . . . .
F11 F -0.11253(12) 0.32439(12) 0.35521(13) 0.0380(3) Uani 1 1 d . . . . .
F12 F -0.00851(13) 0.28360(17) 0.51911(12) 0.0549(4) Uani 1 1 d . . . . .
F13 F 0.02350(11) 0.05920(12) 0.62208(11) 0.0393(3) Uani 1 1 d . . . . .
F14 F 0.06321(12) 0.23405(12) 0.76304(15) 0.0424(3) Uani 1 1 d . . . . .
F15 F 0.05035(11) 0.08377(13) 0.80771(12) 0.0379(3) Uani 1 1 d . . . . .
F16 F 0.68985(10) 0.25107(10) 1.05004(11) 0.0275(2) Uani 1 1 d . . . . .
F17 F 0.60688(11) 0.06163(10) 0.97262(11) 0.0341(3) Uani 1 1 d . . . . .
F18 F 0.59520(11) 0.18027(12) 1.13287(10) 0.0351(3) Uani 1 1 d . . . . .
N1 N 0.67449(13) 0.30207(11) 0.73810(12) 0.0142(2) Uani 1 1 d . . . . .
N2 N 0.62469(13) 0.32260(11) 0.62909(12) 0.0140(2) Uani 1 1 d . . . . .
N3 N 0.25407(13) 0.23354(12) 0.39799(13) 0.0170(3) Uani 1 1 d . . . . .
N4 N 0.17684(13) 0.23918(12) 0.45163(12) 0.0155(2) Uani 1 1 d . . . . .
N5 N 0.30510(13) 0.19037(11) 0.75599(12) 0.0141(2) Uani 1 1 d . . . . .
N6 N 0.43707(13) 0.20150(11) 0.82912(12) 0.0138(2) Uani 1 1 d . . . . .
C1 C 0.80925(15) 0.34020(13) 0.80090(14) 0.0152(3) Uani 1 1 d . . . . .
C2 C 0.85034(15) 0.38695(13) 0.73523(15) 0.0166(3) Uani 1 1 d . . . . .
H2 H 0.9392 0.4198 0.7581 0.020 Uiso 1 1 calc R . . . .
C3 C 0.73035(15) 0.37407(13) 0.62814(15) 0.0148(3) Uani 1 1 d . . . . .
C4 C 0.89329(16) 0.32968(14) 0.92525(15) 0.0185(3) Uani 1 1 d . . . . .
C5 C 0.70944(16) 0.41203(14) 0.52285(16) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.17806(16) 0.22812(15) 0.27712(15) 0.0192(3) Uani 1 1 d D . . . .
C7 C 0.05096(16) 0.23046(16) 0.25025(16) 0.0203(3) Uani 1 1 d . . . . .
H7 H -0.0222 0.2275 0.1728 0.024 Uiso 1 1 calc R . . . .
C8 C 0.05582(15) 0.23815(14) 0.36344(15) 0.0169(3) Uani 1 1 d . . . . .
C9 C 0.2316(3) 0.2121(2) 0.1880(2) 0.0249(5) Uani 0.762(4) 1 d D U P A 1
F7 F 0.3660(3) 0.2529(3) 0.2558(4) 0.0359(7) Uani 0.762(4) 1 d D U P A 1
F8 F 0.1866(2) 0.2721(2) 0.1164(2) 0.0483(7) Uani 0.762(4) 1 d D U P A 1
F9 F 0.1959(2) 0.09783(17) 0.10277(17) 0.0496(6) Uani 0.762(4) 1 d D U P A 1
C9A C 0.2344(8) 0.2444(6) 0.1980(6) 0.0249(5) Uani 0.238(4) 1 d D U P A 2
F8A F 0.2567(7) 0.3526(5) 0.2014(7) 0.0473(18) Uani 0.238(4) 1 d D U P A 2
F7A F 0.3486(9) 0.2165(8) 0.2327(11) 0.033(2) Uani 0.238(4) 1 d D U P A 2
F9A F 0.1481(6) 0.1671(6) 0.0729(5) 0.052(2) Uani 0.238(4) 1 d D U P A 2
C10 C -0.05344(17) 0.24720(17) 0.39182(17) 0.0237(3) Uani 1 1 d . . . . .
C11 C 0.24256(15) 0.15279(13) 0.80870(14) 0.0151(3) Uani 1 1 d . . . . .
C12 C 0.33268(15) 0.13894(14) 0.91747(15) 0.0162(3) Uani 1 1 d . . . . .
H12 H 0.3157 0.1137 0.9728 0.019 Uiso 1 1 calc R . . . .
C13 C 0.45347(15) 0.17087(13) 0.92582(14) 0.0148(3) Uani 1 1 d . . . . .
C14 C 0.09549(17) 0.13264(16) 0.75080(16) 0.0206(3) Uani 1 1 d . . . . .
C15 C 0.58632(16) 0.16662(14) 1.02043(15) 0.0187(3) Uani 1 1 d . . . . .
C16 C 0.31643(18) -0.03602(15) 0.43636(17) 0.0252(3) Uani 1 1 d . . . . .
H16 H 0.2361 -0.0399 0.3642 0.030 Uiso 1 1 calc R . . . .
C17 C 0.31025(19) -0.06268(16) 0.53000(19) 0.0285(4) Uani 1 1 d . . . . .
H17 H 0.2261 -0.0856 0.5217 0.034 Uiso 1 1 calc R . . . .
C18 C 0.4290(2) -0.05616(15) 0.63891(18) 0.0280(4) Uani 1 1 d . . . . .
H18 H 0.4247 -0.0744 0.7039 0.034 Uiso 1 1 calc R . . . .
C19 C 0.55042(18) -0.02346(15) 0.65058(17) 0.0251(3) Uani 1 1 d . . . . .
H19 H 0.6296 -0.0185 0.7247 0.030 Uiso 1 1 calc R . . . .
C20 C 0.56042(17) 0.00296(14) 0.55505(16) 0.0216(3) Uani 1 1 d . . . . .
C21 C 0.5954(2) 0.52965(16) 0.9238(2) 0.0307(4) Uani 1 1 d . . . . .
H21 H 0.6849 0.5453 0.9427 0.037 Uiso 1 1 calc R . . . .
C22 C 0.4941(2) 0.52461(17) 0.8087(2) 0.0351(5) Uani 1 1 d . . . . .
H22 H 0.5141 0.5366 0.7485 0.042 Uiso 1 1 calc R . . . .
C23 C 0.3611(2) 0.50181(17) 0.77924(19) 0.0353(4) Uani 1 1 d . . . . .
H23 H 0.2919 0.4987 0.6994 0.042 Uiso 1 1 calc R . . . .
C24 C 0.3309(2) 0.48403(16) 0.86535(19) 0.0301(4) Uani 1 1 d . . . . .
H24 H 0.2407 0.4687 0.8445 0.036 Uiso 1 1 calc R . . . .
C25 C 0.43275(19) 0.48831(14) 0.98516(17) 0.0245(3) 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
Cu1 N1 1.8720(13) . ?
Cu1 N6 1.8719(13) . ?
Cu2 N2 1.8671(13) . ?
Cu2 N3 1.8738(13) . ?
Cu3 N4 1.8770(13) . ?
Cu3 N5 1.8757(13) . ?
F1 C4 1.3358(18) . ?
F2 C4 1.3441(19) . ?
F3 C4 1.3476(19) . ?
F4 C5 1.3355(19) . ?
F5 C5 1.3440(19) . ?
F6 C5 1.3351(19) . ?
F10 C10 1.334(2) . ?
F11 C10 1.329(2) . ?
F12 C10 1.331(2) . ?
F13 C14 1.337(2) . ?
F14 C14 1.335(2) . ?
F15 C14 1.3292(19) . ?
F16 C15 1.3365(19) . ?
F17 C15 1.341(2) . ?
F18 C15 1.3346(19) . ?
N1 N2 1.3619(17) . ?
N1 C1 1.3451(19) . ?
N2 C3 1.3495(19) . ?
N3 N4 1.3617(18) . ?
N3 C6 1.3493(19) . ?
N4 C8 1.3442(19) . ?
N5 N6 1.3570(17) . ?
N5 C11 1.3462(19) . ?
N6 C13 1.3457(19) . ?
C1 C2 1.385(2) . ?
C1 C4 1.492(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(2) . ?
C3 C5 1.493(2) . ?
C6 C7 1.381(2) . ?
C6 C9 1.502(3) . ?
C6 C9A 1.491(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(2) . ?
C8 C10 1.495(2) . ?
C9 F7 1.340(3) . ?
C9 F8 1.329(3) . ?
C9 F9 1.338(3) . ?
C9A F8A 1.329(5) . ?
C9A F7A 1.334(5) . ?
C9A F9A 1.329(5) . ?
C11 C12 1.385(2) . ?
C11 C14 1.491(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(2) . ?
C13 C15 1.493(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.371(3) . ?
C16 C20 1.412(3) 2_656 ?
C17 H17 0.9500 . ?
C17 C18 1.414(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.372(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.413(3) . ?
C20 C16 1.412(3) 2_656 ?
C20 C20 1.438(3) 2_656 ?
C21 H21 0.9500 . ?
C21 C22 1.373(3) . ?
C21 C25 1.420(3) 2_667 ?
C22 H22 0.9500 . ?
C22 C23 1.406(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.373(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.419(3) . ?
C25 C21 1.420(3) 2_667 ?
C25 C25 1.422(4) 2_667 ?

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
N6 Cu1 N1 178.26(5) . . ?
N2 Cu2 N3 173.08(6) . . ?
N5 Cu3 N4 173.75(6) . . ?
N2 N1 Cu1 119.00(10) . . ?
C1 N1 Cu1 133.09(10) . . ?
C1 N1 N2 107.38(12) . . ?
N1 N2 Cu2 119.60(10) . . ?
C3 N2 Cu2 132.75(11) . . ?
C3 N2 N1 107.43(12) . . ?
N4 N3 Cu2 118.17(10) . . ?
C6 N3 Cu2 132.63(11) . . ?
C6 N3 N4 107.41(12) . . ?
N3 N4 Cu3 118.29(10) . . ?
C8 N4 Cu3 133.46(11) . . ?
C8 N4 N3 107.47(12) . . ?
N6 N5 Cu3 119.66(10) . . ?
C11 N5 Cu3 132.70(11) . . ?
C11 N5 N6 107.63(12) . . ?
N5 N6 Cu1 119.86(9) . . ?
C13 N6 Cu1 132.68(11) . . ?
C13 N6 N5 107.45(12) . . ?
N1 C1 C2 111.16(13) . . ?
N1 C1 C4 120.15(14) . . ?
C2 C1 C4 128.69(14) . . ?
C1 C2 H2 128.5 . . ?
C3 C2 C1 103.08(13) . . ?
C3 C2 H2 128.5 . . ?
N2 C3 C2 110.95(13) . . ?
N2 C3 C5 120.73(13) . . ?
C2 C3 C5 128.30(14) . . ?
F1 C4 F2 107.69(13) . . ?
F1 C4 F3 107.07(12) . . ?
F1 C4 C1 110.96(13) . . ?
F2 C4 F3 105.89(13) . . ?
F2 C4 C1 112.62(13) . . ?
F3 C4 C1 112.28(13) . . ?
F4 C5 F5 107.14(13) . . ?
F4 C5 C3 111.02(13) . . ?
F5 C5 C3 111.75(13) . . ?
F6 C5 F4 107.07(13) . . ?
F6 C5 F5 106.29(13) . . ?
F6 C5 C3 113.22(13) . . ?
N3 C6 C7 110.85(14) . . ?
N3 C6 C9 120.45(16) . . ?
N3 C6 C9A 123.1(3) . . ?
C7 C6 C9 128.53(16) . . ?
C7 C6 C9A 124.8(3) . . ?
C6 C7 H7 128.3 . . ?
C6 C7 C8 103.30(13) . . ?
C8 C7 H7 128.3 . . ?
N4 C8 C7 110.96(14) . . ?
N4 C8 C10 121.92(14) . . ?
C7 C8 C10 127.11(14) . . ?
F7 C9 C6 112.0(3) . . ?
F8 C9 C6 110.6(2) . . ?
F8 C9 F7 107.1(3) . . ?
F8 C9 F9 106.4(2) . . ?
F9 C9 C6 113.7(2) . . ?
F9 C9 F7 106.6(2) . . ?
F8A C9A C6 116.2(6) . . ?
F8A C9A F7A 108.0(6) . . ?
F8A C9A F9A 106.9(6) . . ?
F7A C9A C6 111.1(9) . . ?
F9A C9A C6 108.0(5) . . ?
F9A C9A F7A 106.1(6) . . ?
F10 C10 C8 112.56(15) . . ?
F11 C10 F10 105.77(14) . . ?
F11 C10 F12 107.42(16) . . ?
F11 C10 C8 110.95(14) . . ?
F12 C10 F10 107.22(16) . . ?
F12 C10 C8 112.54(14) . . ?
N5 C11 C12 110.84(13) . . ?
N5 C11 C14 120.80(13) . . ?
C12 C11 C14 128.35(14) . . ?
C11 C12 H12 128.5 . . ?
C13 C12 C11 103.07(13) . . ?
C13 C12 H12 128.5 . . ?
N6 C13 C12 111.01(13) . . ?
N6 C13 C15 121.44(14) . . ?
C12 C13 C15 127.44(14) . . ?
F13 C14 C11 112.47(13) . . ?
F14 C14 F13 105.97(14) . . ?
F14 C14 C11 112.58(14) . . ?
F15 C14 F13 106.72(15) . . ?
F15 C14 F14 107.07(14) . . ?
F15 C14 C11 111.61(13) . . ?
F16 C15 F17 105.81(13) . . ?
F16 C15 C13 112.98(13) . . ?
F17 C15 C13 112.07(13) . . ?
F18 C15 F16 107.67(13) . . ?
F18 C15 F17 106.87(13) . . ?
F18 C15 C13 111.07(13) . . ?
C17 C16 H16 119.3 . . ?
C17 C16 C20 121.41(17) . 2_656 ?
C20 C16 H16 119.3 2_656 . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.04(17) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.95(17) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.59(17) . . ?
C20 C19 H19 119.2 . . ?
C16 C20 C19 122.99(16) 2_656 . ?
C16 C20 C20 118.7(2) 2_656 2_656 ?
C19 C20 C20 118.3(2) . 2_656 ?
C22 C21 H21 119.8 . . ?
C22 C21 C25 120.47(19) . 2_667 ?
C25 C21 H21 119.8 2_667 . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.54(18) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.31(19) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.6 . . ?
C23 C24 C25 120.8(2) . . ?
C25 C24 H24 119.6 . . ?
C21 C25 C25 119.1(2) 2_667 2_667 ?
C24 C25 C21 122.09(19) . 2_667 ?
C24 C25 C25 118.8(2) . 2_667 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 N2 Cu2 -12.60(14) . . . . ?
Cu1 N1 N2 C3 172.12(9) . . . . ?
Cu1 N1 C1 C2 -170.85(11) . . . . ?
Cu1 N1 C1 C4 8.7(2) . . . . ?
Cu1 N6 C13 C12 -178.59(11) . . . . ?
Cu1 N6 C13 C15 -2.2(2) . . . . ?
Cu2 N2 C3 C2 -173.84(11) . . . . ?
Cu2 N2 C3 C5 7.8(2) . . . . ?
Cu2 N3 N4 Cu3 -22.60(15) . . . . ?
Cu2 N3 N4 C8 166.16(10) . . . . ?
Cu2 N3 C6 C7 -163.80(12) . . . . ?
Cu2 N3 C6 C9 20.5(3) . . . . ?
Cu2 N3 C6 C9A 4.0(4) . . . . ?
Cu3 N4 C8 C7 -168.67(12) . . . . ?
Cu3 N4 C8 C10 12.6(2) . . . . ?
Cu3 N5 N6 Cu1 -0.21(15) . . . . ?
Cu3 N5 N6 C13 -179.14(10) . . . . ?
Cu3 N5 C11 C12 178.92(11) . . . . ?
Cu3 N5 C11 C14 -1.6(2) . . . . ?
N1 N2 C3 C2 0.57(17) . . . . ?
N1 N2 C3 C5 -177.82(13) . . . . ?
N1 C1 C2 C3 -0.05(17) . . . . ?
N1 C1 C4 F1 -177.63(13) . . . . ?
N1 C1 C4 F2 61.57(19) . . . . ?
N1 C1 C4 F3 -57.86(18) . . . . ?
N2 N1 C1 C2 0.40(16) . . . . ?
N2 N1 C1 C4 179.97(13) . . . . ?
N2 C3 C5 F4 169.05(13) . . . . ?
N2 C3 C5 F5 49.5(2) . . . . ?
N2 C3 C5 F6 -70.48(18) . . . . ?
N3 N4 C8 C7 0.69(18) . . . . ?
N3 N4 C8 C10 -178.07(15) . . . . ?
N3 C6 C7 C8 0.23(19) . . . . ?
N3 C6 C9 F7 -25.7(3) . . . . ?
N3 C6 C9 F8 -145.1(2) . . . . ?
N3 C6 C9 F9 95.2(2) . . . . ?
N3 C6 C9A F8A -98.8(6) . . . . ?
N3 C6 C9A F7A 25.1(6) . . . . ?
N3 C6 C9A F9A 141.1(4) . . . . ?
N4 N3 C6 C7 0.17(19) . . . . ?
N4 N3 C6 C9 -175.54(17) . . . . ?
N4 N3 C6 C9A 168.0(3) . . . . ?
N4 C8 C10 F10 -106.67(18) . . . . ?
N4 C8 C10 F11 135.02(16) . . . . ?
N4 C8 C10 F12 14.6(2) . . . . ?
N5 N6 C13 C12 0.15(17) . . . . ?
N5 N6 C13 C15 176.55(13) . . . . ?
N5 C11 C12 C13 -0.04(17) . . . . ?
N5 C11 C14 F13 53.4(2) . . . . ?
N5 C11 C14 F14 -66.23(19) . . . . ?
N5 C11 C14 F15 173.32(14) . . . . ?
N6 N5 C11 C12 0.14(17) . . . . ?
N6 N5 C11 C14 179.57(13) . . . . ?
N6 C13 C15 F16 35.0(2) . . . . ?
N6 C13 C15 F17 -84.42(18) . . . . ?
N6 C13 C15 F18 156.13(14) . . . . ?
C1 N1 N2 Cu2 174.70(10) . . . . ?
C1 N1 N2 C3 -0.58(15) . . . . ?
C1 C2 C3 N2 -0.32(17) . . . . ?
C1 C2 C3 C5 177.92(15) . . . . ?
C2 C1 C4 F1 1.9(2) . . . . ?
C2 C1 C4 F2 -118.94(17) . . . . ?
C2 C1 C4 F3 121.63(17) . . . . ?
C2 C3 C5 F4 -9.0(2) . . . . ?
C2 C3 C5 F5 -128.59(17) . . . . ?
C2 C3 C5 F6 111.43(18) . . . . ?
C4 C1 C2 C3 -179.58(15) . . . . ?
C6 N3 N4 Cu3 170.73(11) . . . . ?
C6 N3 N4 C8 -0.51(17) . . . . ?
C6 C7 C8 N4 -0.56(19) . . . . ?
C6 C7 C8 C10 178.11(17) . . . . ?
C7 C6 C9 F7 159.4(2) . . . . ?
C7 C6 C9 F8 40.0(3) . . . . ?
C7 C6 C9 F9 -79.7(3) . . . . ?
C7 C6 C9A F8A 67.3(6) . . . . ?
C7 C6 C9A F7A -168.8(4) . . . . ?
C7 C6 C9A F9A -52.8(6) . . . . ?
C7 C8 C10 F10 74.8(2) . . . . ?
C7 C8 C10 F11 -43.5(2) . . . . ?
C7 C8 C10 F12 -163.91(18) . . . . ?
C9 C6 C7 C8 175.50(19) . . . . ?
C9A C6 C7 C8 -167.3(3) . . . . ?
C11 N5 N6 Cu1 178.76(10) . . . . ?
C11 N5 N6 C13 -0.17(16) . . . . ?
C11 C12 C13 N6 -0.07(17) . . . . ?
C11 C12 C13 C15 -176.19(15) . . . . ?
C12 C11 C14 F13 -127.27(17) . . . . ?
C12 C11 C14 F14 113.10(18) . . . . ?
C12 C11 C14 F15 -7.3(2) . . . . ?
C12 C13 C15 F16 -149.22(15) . . . . ?
C12 C13 C15 F17 91.34(19) . . . . ?
C12 C13 C15 F18 -28.1(2) . . . . ?
C14 C11 C12 C13 -179.42(15) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
C18 C19 C20 C16 -179.53(16) . . . 2_656 ?
C18 C19 C20 C20 1.2(3) . . . 2_656 ?
C20 C16 C17 C18 0.7(3) 2_656 . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C24 C25 C21 179.97(16) . . . 2_667 ?
C23 C24 C25 C25 0.2(3) . . . 2_667 ?
C25 C21 C22 C23 0.1(3) 2_667 . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
