# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

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

data_a
_audit_block_doi                 10.5517/ccdc.csd.cc20t5jk
_database_code_depnum_ccdc_archive 'CCDC 1871238'
_audit_update_record             
;
2018-10-03 deposited with the CCDC.
2018-10-31 downloaded from the CCDC.
;
_audit_creation_date             2018-10-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H16 Cu3 F24 N8'
_chemical_formula_sum            'C36 H16 Cu3 F24 N8'
_chemical_formula_weight         1207.19
_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'
Cu Cu 0.3201 1.2651 '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'
N N 0.0061 0.0033 '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                   9.1317(11)
_cell_length_b                   11.0607(13)
_cell_length_c                   11.7651(14)
_cell_angle_alpha                72.527(2)
_cell_angle_beta                 70.675(2)
_cell_angle_gamma                69.170(2)
_cell_volume                     1025.4(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5962
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.691
_cell_measurement_theta_min      2.466
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.785
_exptl_absorpt_coefficient_mu    1.693
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0668 before and 0.0281 after correction. The Ratio of minimum to maximum transmission is 0.7654. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.955
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             591
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_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            19293
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_min         1.875
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                4233
_reflns_number_total             5444
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         3.637
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0378
_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)+(0.0514P)²+0.9215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1017
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C18(H18), C14(H14), C17(H17), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.5000 0.5000 0.5000 0.01581(10) Uani 1 2 d S T P . .
Cu2 Cu 0.36670(4) 0.23821(3) 0.69051(3) 0.01941(9) Uani 1 1 d . . . . .
F12 F 0.8446(2) 0.49592(15) 0.45616(15) 0.0266(3) Uani 1 1 d . . . . .
F10 F 0.94968(19) 0.37926(16) 0.31511(14) 0.0263(3) Uani 1 1 d . . . . .
F1 F 0.5752(2) 0.67565(17) 0.60250(15) 0.0311(4) Uani 1 1 d . . . . .
F2 F 0.3352(2) 0.80470(16) 0.65730(17) 0.0367(4) Uani 1 1 d . . . . .
F6 F 0.2802(2) 0.19896(17) 0.96702(17) 0.0402(5) Uani 1 1 d . . . . .
F11 F 1.0625(2) 0.33153(17) 0.46363(17) 0.0316(4) Uani 1 1 d . . . . .
F7 F 0.5978(2) -0.01545(17) 0.80324(16) 0.0363(4) Uani 1 1 d . . . . .
F9 F 0.8541(2) -0.09769(17) 0.72692(19) 0.0434(5) Uani 1 1 d . . . . .
F3 F 0.4878(3) 0.72205(19) 0.78408(16) 0.0411(5) Uani 1 1 d . . . . .
F4 F 0.2176(3) 0.3398(2) 1.08084(15) 0.0431(5) Uani 1 1 d . . . . .
F8 F 0.6799(3) -0.08284(17) 0.63252(18) 0.0412(5) Uani 1 1 d . . . . .
F5 F 0.0501(2) 0.3453(2) 0.98607(18) 0.0425(5) Uani 1 1 d . . . . .
N1 N 0.3987(3) 0.4933(2) 0.67953(19) 0.0178(4) Uani 1 1 d . . . . .
N4 N 0.6552(3) 0.3218(2) 0.54193(19) 0.0186(4) Uani 1 1 d . . . . .
N2 N 0.3342(3) 0.3947(2) 0.75413(19) 0.0184(4) Uani 1 1 d . . . . .
N3 N 0.6013(3) 0.2170(2) 0.61328(19) 0.0195(4) Uani 1 1 d . . . . .
C6 C 0.8194(3) 0.2806(2) 0.5133(2) 0.0193(5) Uani 1 1 d . . . . .
C1 C 0.3817(3) 0.5764(2) 0.7501(2) 0.0205(5) Uani 1 1 d . . . . .
C2 C 0.3071(3) 0.5329(3) 0.8716(2) 0.0215(5) Uani 1 1 d . . . . .
H2 H 0.2809 0.5720 0.9401 0.026 Uiso 1 1 calc R . . . .
C13 C 0.0138(3) 0.1978(3) 0.7891(2) 0.0244(5) Uani 1 1 d . . . . .
C8 C 0.2064(3) 0.3260(3) 0.9753(2) 0.0256(6) Uani 1 1 d . . . . .
C4 C 0.7321(3) 0.1132(2) 0.6275(2) 0.0217(5) Uani 1 1 d . . . . .
C3 C 0.2801(3) 0.4182(2) 0.8688(2) 0.0200(5) Uani 1 1 d . . . . .
C5 C 0.8731(3) 0.1480(2) 0.5664(2) 0.0225(5) Uani 1 1 d . . . . .
H5 H 0.9815 0.0939 0.5618 0.027 Uiso 1 1 calc R . . . .
C10 C 0.9189(3) 0.3715(2) 0.4368(2) 0.0220(5) Uani 1 1 d . . . . .
C12 C 0.1827(4) 0.1637(3) 0.7206(3) 0.0259(6) Uani 1 1 d . . . . .
C9 C 0.7150(4) -0.0199(3) 0.6988(3) 0.0297(6) Uani 1 1 d . . . . .
C7 C 0.4454(4) 0.6936(3) 0.6985(3) 0.0270(6) Uani 1 1 d . . . . .
C18 C -0.0836(4) 0.3283(3) 0.7788(3) 0.0295(6) Uani 1 1 d . . . . .
H18 H -0.0387 0.3984 0.7298 0.035 Uiso 1 1 calc R . . . .
C11 C 0.3078(4) 0.1000(3) 0.6613(3) 0.0315(6) Uani 1 1 d . . . . .
C14 C -0.0529(4) 0.0958(3) 0.8631(3) 0.0327(6) Uani 1 1 d . . . . .
H14 H 0.0130 0.0067 0.8706 0.039 Uiso 1 1 calc R . . . .
C17 C -0.2473(4) 0.3558(3) 0.8405(3) 0.0348(7) Uani 1 1 d . . . . .
H17 H -0.3144 0.4445 0.8319 0.042 Uiso 1 1 calc R . . . .
C15 C -0.2149(4) 0.1243(4) 0.9256(3) 0.0416(8) Uani 1 1 d . . . . .
H15 H -0.2597 0.0548 0.9765 0.050 Uiso 1 1 calc R . . . .
C16 C -0.3121(4) 0.2543(4) 0.9140(3) 0.0386(7) Uani 1 1 d . . . . .
H16 H -0.4234 0.2735 0.9568 0.046 Uiso 1 1 calc R . . . .
H11 H 0.371(5) 0.051(4) 0.615(4) 0.045(11) 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 N1 1.996(2) 2_666 ?
Cu1 N1 1.996(2) . ?
Cu1 N4 2.007(2) 2_666 ?
Cu1 N4 2.007(2) . ?
Cu2 N2 1.978(2) . ?
Cu2 N3 1.988(2) . ?
Cu2 C12 2.011(3) . ?
Cu2 C11 1.941(3) . ?
F12 C10 1.352(3) . ?
F10 C10 1.346(3) . ?
F1 C7 1.342(3) . ?
F2 C7 1.358(3) . ?
F6 C8 1.343(3) . ?
F11 C10 1.339(3) . ?
F7 C9 1.337(3) . ?
F9 C9 1.339(3) . ?
F3 C7 1.341(3) . ?
F4 C8 1.335(3) . ?
F8 C9 1.359(4) . ?
F5 C8 1.334(3) . ?
N1 N2 1.359(3) . ?
N1 C1 1.352(3) . ?
N4 N3 1.355(3) . ?
N4 C6 1.357(3) . ?
N2 C3 1.345(3) . ?
N3 C4 1.347(3) . ?
C6 C5 1.387(3) . ?
C6 C10 1.488(4) . ?
C1 C2 1.383(4) . ?
C1 C7 1.489(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(4) . ?
C13 C12 1.455(4) . ?
C13 C18 1.393(4) . ?
C13 C14 1.397(4) . ?
C8 C3 1.492(4) . ?
C4 C5 1.377(4) . ?
C4 C9 1.494(4) . ?
C5 H5 0.9500 . ?
C12 C11 1.218(4) . ?
C18 H18 0.9500 . ?
C18 C17 1.394(4) . ?
C11 H11 0.82(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(5) . ?
C17 H17 0.9500 . ?
C17 C16 1.382(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(5) . ?
C16 H16 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 N1 180.0 2_666 . ?
N1 Cu1 N4 90.95(8) 2_666 . ?
N1 Cu1 N4 89.05(8) . . ?
N1 Cu1 N4 90.95(8) . 2_666 ?
N1 Cu1 N4 89.05(8) 2_666 2_666 ?
N4 Cu1 N4 180.0 . 2_666 ?
N2 Cu2 N3 94.12(9) . . ?
N2 Cu2 C12 121.24(10) . . ?
N3 Cu2 C12 144.64(10) . . ?
C11 Cu2 N2 157.09(12) . . ?
C11 Cu2 N3 108.79(12) . . ?
C11 Cu2 C12 35.84(13) . . ?
N2 N1 Cu1 122.60(16) . . ?
C1 N1 Cu1 129.97(17) . . ?
C1 N1 N2 107.4(2) . . ?
N3 N4 Cu1 121.14(16) . . ?
N3 N4 C6 107.60(19) . . ?
C6 N4 Cu1 131.24(17) . . ?
N1 N2 Cu2 119.54(16) . . ?
C3 N2 Cu2 131.96(17) . . ?
C3 N2 N1 107.5(2) . . ?
N4 N3 Cu2 120.97(16) . . ?
C4 N3 Cu2 131.17(17) . . ?
C4 N3 N4 107.5(2) . . ?
N4 C6 C5 110.2(2) . . ?
N4 C6 C10 122.0(2) . . ?
C5 C6 C10 127.8(2) . . ?
N1 C1 C2 111.0(2) . . ?
N1 C1 C7 121.8(2) . . ?
C2 C1 C7 127.2(2) . . ?
C1 C2 H2 128.5 . . ?
C1 C2 C3 103.0(2) . . ?
C3 C2 H2 128.5 . . ?
C18 C13 C12 121.8(3) . . ?
C18 C13 C14 119.6(3) . . ?
C14 C13 C12 118.5(3) . . ?
F6 C8 C3 112.0(2) . . ?
F4 C8 F6 107.4(2) . . ?
F4 C8 C3 110.6(2) . . ?
F5 C8 F6 106.0(2) . . ?
F5 C8 F4 107.1(2) . . ?
F5 C8 C3 113.4(2) . . ?
N3 C4 C5 111.1(2) . . ?
N3 C4 C9 121.2(2) . . ?
C5 C4 C9 127.6(2) . . ?
N2 C3 C2 111.1(2) . . ?
N2 C3 C8 121.7(2) . . ?
C2 C3 C8 127.1(2) . . ?
C6 C5 H5 128.2 . . ?
C4 C5 C6 103.5(2) . . ?
C4 C5 H5 128.2 . . ?
F12 C10 C6 111.3(2) . . ?
F10 C10 F12 106.8(2) . . ?
F10 C10 C6 113.2(2) . . ?
F11 C10 F12 107.7(2) . . ?
F11 C10 F10 106.8(2) . . ?
F11 C10 C6 110.8(2) . . ?
C13 C12 Cu2 133.2(2) . . ?
C11 C12 Cu2 68.94(19) . . ?
C11 C12 C13 157.7(3) . . ?
F7 C9 F9 108.2(2) . . ?
F7 C9 F8 106.4(2) . . ?
F7 C9 C4 113.4(2) . . ?
F9 C9 F8 106.4(2) . . ?
F9 C9 C4 110.6(2) . . ?
F8 C9 C4 111.6(2) . . ?
F1 C7 F2 106.0(2) . . ?
F1 C7 C1 112.5(2) . . ?
F2 C7 C1 113.0(2) . . ?
F3 C7 F1 107.8(2) . . ?
F3 C7 F2 106.1(2) . . ?
F3 C7 C1 111.0(2) . . ?
C13 C18 H18 120.1 . . ?
C13 C18 C17 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
Cu2 C11 H11 121(3) . . ?
C12 C11 Cu2 75.21(19) . . ?
C12 C11 H11 162(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT094_a                   
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       9.28 Report
RESPONSE: Analysis of reciprocal space have revealed that crystal of 
{[((CF3)2Pz)4Cu3]/Phenylacetylene2} is 
the growth twin with at least 5 different domains. All attempts to integrate 
frames within two- , three and even four domains model lead to the same value 
of the residual density ca. 3.6 e-3. As the result used the model without 
twining in which the maximum for electron density is in the special position 
and cannot be refined. Considering that all other peaks of residual electron 
density are located \"i?/>?in the expected positions ( centers of bonds)\"i?/>? and that 
all anisotropic displacement parameters of atoms are rather accurate and reliable 
we came to conclusion that maxima located at  0.5  0.0  0.5  with the height  3.57e A-3 
should be considered as the \"i?/>?false peak\"i?/>? due to unresolved twining.  It should be noted 
that all other peaks are not more than 0.7 eA3. 
;
_vrf_PLAT097_a                   
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       3.64 eA-3  
RESPONSE: Analysis of reciprocal space have revealed that crystal of 
{[((CF3)2Pz)4Cu3]/Phenylacetylene2} is 
the growth twin with at least 5 different domains. All attempts to integrate 
frames within two- , three and even four domains model lead to the same value 
of the residual density ca. 3.6 e-3. As the result used the model without 
twining in which the maximum for electron density is in the special position 
and cannot be refined. Considering that all other peaks of residual electron 
density are located \"i?/>?in the expected positions ( centers of bonds)\"i?/>? and that 
all anisotropic displacement parameters of atoms are rather accurate and reliable 
we came to conclusion that maxima located at  0.5  0.0  0.5  with the height  3.57e A-3 
should be considered as the \"i?/>?false peak\"i?/>? due to unresolved twining.  It should be noted 
that all other peaks are not more than 0.7 eA3. 
;
_vrf_PLAT971_a                   
;
PROBLEM: Check Calcd Resid. Dens.  2.36A   From C11             3.59 eA-3  
RESPONSE: Analysis of reciprocal space have revealed that crystal of 
{[((CF3)2Pz)4Cu3]/Phenylacetylene2} is 
the growth twin with at least 5 different domains. All attempts to integrate 
frames within two- , three and even four domains model lead to the same value 
of the residual density ca. 3.6 e-3. As the result used the model without 
twining in which the maximum for electron density is in the special position 
and cannot be refined. Considering that all other peaks of residual electron 
density are located \"i?/>?in the expected positions ( centers of bonds)\"i?/>? and that 
all anisotropic displacement parameters of atoms are rather accurate and reliable 
we came to conclusion that maxima located at  0.5  0.0  0.5  with the height  3.57e A-3 
should be considered as the \"i?/>?false peak\"i?/>? due to unresolved twining.  It should be noted 
that all other peaks are not more than 0.7 eA3. 
;
####################################################################### 
# 
# 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_a_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc20t5kl
_database_code_depnum_ccdc_archive 'CCDC 1871239'
_audit_update_record             
;
2018-10-03 deposited with the CCDC.
2018-10-31 downloaded from the CCDC.
;
_audit_creation_date             2018-10-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H32 Cu3 F24 N8'
_chemical_formula_sum            'C36 H32 Cu3 F24 N8'
_chemical_formula_weight         1223.31
_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'
Cu Cu 0.3201 1.2651 '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'
N N 0.0061 0.0033 '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                   8.550(9)
_cell_length_b                   10.660(12)
_cell_length_c                   13.468(14)
_cell_angle_alpha                107.62(3)
_cell_angle_beta                 100.88(2)
_cell_angle_gamma                95.18(2)
_cell_volume                     1135(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7996
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.691
_cell_measurement_theta_min      2.466
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.739
_exptl_absorpt_coefficient_mu    1.531
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0668 before and 0.0281 after correction. The Ratio of minimum to maximum transmission is 0.7654. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             607
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15153
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.571
_diffrn_reflns_theta_min         1.629
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                6032
_reflns_number_total             6937
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6937
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+0.2851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0717
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C14(H14a,H14b), C15(H15a,H15b), C16(H16a,H16b), C17(H17a,H17b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7)
2.c Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.5000 0.5000 0.5000 0.01442(5) Uani 1 2 d S T P . .
Cu2 Cu 0.43469(2) 0.44466(2) 0.72231(2) 0.01892(5) Uani 1 1 d . . . . .
F1 F 0.32780(10) 0.32533(8) 0.28596(7) 0.02552(17) Uani 1 1 d . . . . .
F2 F 0.46474(12) 0.16235(10) 0.26403(7) 0.0329(2) Uani 1 1 d . . . . .
F3 F 0.20456(13) 0.12165(9) 0.22835(7) 0.0367(2) Uani 1 1 d . . . . .
F4 F 0.24084(15) 0.20060(10) 0.72197(8) 0.0437(3) Uani 1 1 d . . . . .
F5 F 0.38029(13) 0.04559(11) 0.67022(9) 0.0409(2) Uani 1 1 d . . . . .
F6 F 0.12977(12) 0.01730(10) 0.59415(8) 0.0389(2) Uani 1 1 d . . . . .
F7 F 0.14048(14) 0.52674(11) 0.81759(8) 0.0425(2) Uani 1 1 d . . . . .
F8 F 0.27247(14) 0.72556(11) 0.88412(8) 0.0421(2) Uani 1 1 d . . . . .
F9 F 0.01980(14) 0.69440(15) 0.81008(10) 0.0576(4) Uani 1 1 d . . . . .
F10 F 0.28572(13) 0.79541(9) 0.44723(8) 0.0348(2) Uani 1 1 d . . . . .
F11 F 0.03975(12) 0.69626(12) 0.40355(9) 0.0427(3) Uani 1 1 d . . . . .
F12 F 0.23098(12) 0.58440(9) 0.36037(7) 0.0319(2) Uani 1 1 d . . . . .
N1 N 0.40182(13) 0.31961(10) 0.49390(9) 0.0175(2) Uani 1 1 d . . . . .
N2 N 0.38258(13) 0.29439(11) 0.58441(9) 0.0185(2) Uani 1 1 d . . . . .
N3 N 0.32360(13) 0.57719(11) 0.56775(9) 0.0181(2) Uani 1 1 d . . . . .
N4 N 0.31147(13) 0.56625(11) 0.66400(9) 0.0192(2) Uani 1 1 d . . . . .
C1 C 0.33563(16) 0.20889(12) 0.40934(10) 0.0188(2) Uani 1 1 d . . . . .
C2 C 0.27125(17) 0.10924(13) 0.44368(11) 0.0229(3) Uani 1 1 d . . . . .
H2 H 0.2175 0.0219 0.4018 0.027 Uiso 1 1 calc R . . . .
C3 C 0.30463(16) 0.16856(13) 0.55440(11) 0.0201(2) Uani 1 1 d . . . . .
C4 C 0.33379(17) 0.20413(13) 0.29728(11) 0.0222(3) Uani 1 1 d . . . . .
C5 C 0.26412(18) 0.10854(14) 0.63523(12) 0.0259(3) Uani 1 1 d . . . . .
C6 C 0.19458(16) 0.63465(14) 0.69565(11) 0.0225(3) Uani 1 1 d . . . . .
C7 C 0.12695(17) 0.69072(15) 0.62022(12) 0.0259(3) Uani 1 1 d . . . . .
H7 H 0.0427 0.7431 0.6223 0.031 Uiso 1 1 calc R . . . .
C8 C 0.21287(16) 0.65143(13) 0.54085(11) 0.0203(2) Uani 1 1 d . . . . .
C9 C 0.19254(18) 0.68192(15) 0.43861(12) 0.0254(3) Uani 1 1 d . . . . .
C10 C 0.15600(18) 0.64539(17) 0.80139(13) 0.0299(3) Uani 1 1 d . . . . .
C11 C 0.5503(2) 0.52216(17) 0.87363(12) 0.0320(3) Uani 1 1 d . . . . .
H11 H 0.545(3) 0.600(3) 0.9135(19) 0.053(7) Uiso 1 1 d . . . . .
C12 C 0.58848(18) 0.41196(15) 0.84027(11) 0.0262(3) Uani 1 1 d . . . . .
C13 C 0.66647(18) 0.29118(15) 0.83206(13) 0.0276(3) Uani 1 1 d . . . . .
H13A H 0.6570 0.2410 0.7556 0.033 Uiso 1 1 calc R . . . .
H13B H 0.6085 0.2330 0.8629 0.033 Uiso 1 1 calc R . . . .
C14 C 0.84507(17) 0.32441(15) 0.89009(12) 0.0254(3) Uani 1 1 d . . . . .
H14A H 0.9049 0.3802 0.8583 0.030 Uiso 1 1 calc R . . . .
H14B H 0.8560 0.3754 0.9665 0.030 Uiso 1 1 calc R . . . .
C15 C 0.91586(18) 0.19548(15) 0.88018(13) 0.0289(3) Uani 1 1 d . . . . .
H15A H 0.8529 0.1402 0.9108 0.035 Uiso 1 1 calc R . . . .
H15B H 0.9023 0.1453 0.8033 0.035 Uiso 1 1 calc R . . . .
C16 C 1.09390(18) 0.21484(16) 0.93525(12) 0.0286(3) Uani 1 1 d . . . . .
H16A H 1.1079 0.2583 1.0132 0.034 Uiso 1 1 calc R . . . .
H16B H 1.1576 0.2741 0.9083 0.034 Uiso 1 1 calc R . . . .
C17 C 1.15693(19) 0.08081(18) 0.91446(15) 0.0341(3) Uani 1 1 d . . . . .
H17A H 1.0957 0.0235 0.9443 0.041 Uiso 1 1 calc R . . . .
H17B H 1.1369 0.0356 0.8363 0.041 Uiso 1 1 calc R . . . .
C18 C 1.3359(2) 0.0953(2) 0.96321(17) 0.0458(4) Uani 1 1 d . . . . .
H18A H 1.3973 0.1538 0.9355 0.069 Uiso 1 1 calc GR . . . .
H18B H 1.3701 0.0074 0.9444 0.069 Uiso 1 1 calc GR . . . .
H18C H 1.3557 0.1339 1.0412 0.069 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
Cu1 N1 1.999(2) 2_666 ?
Cu1 N1 1.999(2) . ?
Cu1 N3 2.0184(18) . ?
Cu1 N3 2.0184(18) 2_666 ?
Cu2 N2 1.993(2) . ?
Cu2 N4 1.9893(18) . ?
Cu2 C11 1.971(2) . ?
Cu2 C12 2.001(2) . ?
F1 C4 1.350(2) . ?
F2 C4 1.346(2) . ?
F3 C4 1.3413(19) . ?
F4 C5 1.340(2) . ?
F5 C5 1.340(2) . ?
F6 C5 1.343(2) . ?
F7 C10 1.346(2) . ?
F8 C10 1.347(2) . ?
F9 C10 1.329(2) . ?
F10 C9 1.348(2) . ?
F11 C9 1.342(2) . ?
F12 C9 1.352(2) . ?
N1 N2 1.361(2) . ?
N1 C1 1.354(2) . ?
N2 C3 1.347(2) . ?
N3 N4 1.358(2) . ?
N3 C8 1.3540(19) . ?
N4 C6 1.348(2) . ?
C1 C2 1.390(2) . ?
C1 C4 1.492(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(2) . ?
C3 C5 1.496(2) . ?
C6 C7 1.390(2) . ?
C6 C10 1.495(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.392(2) . ?
C8 C9 1.491(2) . ?
C11 H11 0.86(3) . ?
C11 C12 1.222(3) . ?
C12 C13 1.487(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.534(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.531(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.528(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.538(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.521(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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 Cu1 N1 180.0 2_666 . ?
N1 Cu1 N3 88.84(7) . . ?
N1 Cu1 N3 88.84(7) 2_666 2_666 ?
N1 Cu1 N3 91.16(7) . 2_666 ?
N1 Cu1 N3 91.16(7) 2_666 . ?
N3 Cu1 N3 180.0 2_666 . ?
N2 Cu2 C12 114.17(9) . . ?
N4 Cu2 N2 94.87(9) . . ?
N4 Cu2 C12 150.58(6) . . ?
C11 Cu2 N2 149.99(7) . . ?
C11 Cu2 N4 115.04(8) . . ?
C11 Cu2 C12 35.82(8) . . ?
N2 N1 Cu1 120.96(9) . . ?
C1 N1 Cu1 130.83(11) . . ?
C1 N1 N2 108.07(13) . . ?
N1 N2 Cu2 118.88(11) . . ?
C3 N2 Cu2 132.92(10) . . ?
C3 N2 N1 107.27(12) . . ?
N4 N3 Cu1 119.05(9) . . ?
C8 N3 Cu1 132.84(10) . . ?
C8 N3 N4 107.90(11) . . ?
N3 N4 Cu2 120.04(9) . . ?
C6 N4 Cu2 131.95(11) . . ?
C6 N4 N3 107.46(11) . . ?
N1 C1 C2 110.39(14) . . ?
N1 C1 C4 121.73(13) . . ?
C2 C1 C4 127.87(12) . . ?
C1 C2 H2 128.4 . . ?
C1 C2 C3 103.15(13) . . ?
C3 C2 H2 128.4 . . ?
N2 C3 C2 111.12(12) . . ?
N2 C3 C5 121.15(13) . . ?
C2 C3 C5 127.73(14) . . ?
F1 C4 C1 111.55(11) . . ?
F2 C4 F1 106.45(11) . . ?
F2 C4 C1 113.25(12) . . ?
F3 C4 F1 107.06(12) . . ?
F3 C4 F2 106.97(14) . . ?
F3 C4 C1 111.20(12) . . ?
F4 C5 F6 107.69(14) . . ?
F4 C5 C3 112.03(14) . . ?
F5 C5 F4 106.50(14) . . ?
F5 C5 F6 106.11(14) . . ?
F5 C5 C3 112.71(14) . . ?
F6 C5 C3 111.43(13) . . ?
N4 C6 C7 111.11(13) . . ?
N4 C6 C10 120.36(13) . . ?
C7 C6 C10 128.51(14) . . ?
C6 C7 H7 128.5 . . ?
C6 C7 C8 103.09(14) . . ?
C8 C7 H7 128.5 . . ?
N3 C8 C7 110.45(13) . . ?
N3 C8 C9 121.95(12) . . ?
C7 C8 C9 127.60(13) . . ?
F10 C9 F12 106.10(13) . . ?
F10 C9 C8 113.27(13) . . ?
F11 C9 F10 106.43(13) . . ?
F11 C9 F12 107.59(13) . . ?
F11 C9 C8 111.18(12) . . ?
F12 C9 C8 111.88(13) . . ?
F7 C10 F8 105.64(14) . . ?
F7 C10 C6 112.19(13) . . ?
F8 C10 C6 112.36(14) . . ?
F9 C10 F7 107.77(14) . . ?
F9 C10 F8 107.00(15) . . ?
F9 C10 C6 111.53(13) . . ?
Cu2 C11 H11 123.7(16) . . ?
C12 C11 Cu2 73.41(11) . . ?
C12 C11 H11 162.8(16) . . ?
C11 C12 Cu2 70.76(11) . . ?
C11 C12 C13 162.95(15) . . ?
C13 C12 Cu2 126.24(11) . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C12 C13 C14 112.75(13) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C13 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 C13 109.71(13) . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C14 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 C14 114.96(13) . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C15 C16 C17 111.15(14) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C16 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 C16 113.22(16) . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
