# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_rad573a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1934981'
loop_
_audit_author_name
_audit_author_address
'Rasika Dias'
;The University of Texas at Arlington
United States of America
;
_audit_update_record             
;
2019-06-18 deposited with the CCDC.	2019-09-05 downloaded from the CCDC.
;
_audit_creation_date             2019-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H4 Cu2 F12 N4'
_chemical_formula_sum            'C12 H4 Cu2 F12 N4'
_chemical_formula_weight         559.27
_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                   9.2461(15)
_cell_length_b                   9.4479(16)
_cell_length_c                   11.1313(18)
_cell_angle_alpha                95.590(4)
_cell_angle_beta                 113.485(2)
_cell_angle_gamma                104.311(3)
_cell_volume                     842.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.14
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.816
_shelx_estimated_absorpt_T_min   0.619
_exptl_absorpt_coefficient_mu    2.657
_exptl_absorpt_correction_T_max  0.5638
_exptl_absorpt_correction_T_min  0.4671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0703 before and 0.0506 after correction. The Ratio of minimum to maximum transmission is 0.8285. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rods
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18287
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.147
_diffrn_reflns_theta_min         2.459
_diffrn_ambient_temperature      100.29
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  
'Bruker D8 Quest with a Photon 100 CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3871
_reflns_number_total             4530
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4530
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.038
_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)+(0.0336P)²+0.9779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0787
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C7A-C6 \\sim C7-C6 \\sim C8-C7A \\sim C8-C7 \\sim C2A-C1 \\sim C2-C1 \\sim
C3-C2A \\sim C3-C2
 with sigma of 0.005
 N2-C3 \\sim N2A-C3 \\sim N1-C1 \\sim N1A-C1 \\sim N3-C6 \\sim N3A-C6 \\sim
N4A-C8 \\sim N4-C8
 with sigma of 0.005
3. Restrained planarity
 N1A, C1, C2A, C3, N2A
 with sigma of 0.005
 N1, C1, C2, C3, N2
 with sigma of 0.005
 N3, N4, C8, C7, C6
 with sigma of 0.005
 N3A, N4A, C8, C7A, C6
 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
C7 \\sim C7A \\sim C2 \\sim C2A: within 1.7A with sigma of 0.002 and sigma for
terminal atoms of 0.002
Uanis(N2A) \\sim Ueq, Uanis(N1A) \\sim Ueq, Uanis(N4A) \\sim Ueq, Uanis(N3A)
\\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.004
Uanis(C12A) \\sim Ueq, Uanis(C11A) \\sim Ueq: with sigma of 0.004 and sigma for
terminal atoms of 0.004
5. Rigid body (RIGU) restrains
 C2A, C2, C7, C7A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N2A, N1A, N4A, N3A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C11A, C12A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Others
 Sof(Cu1A)=Sof(Cu2A)=Sof(N1A)=Sof(N2A)=Sof(N3A)=Sof(N4A)=Sof(C11A)=Sof(H11A)=
 Sof(C12A)=Sof(H12A)=Sof(C2A)=Sof(H2A)=Sof(C7A)=Sof(H7A)=1-FVAR(1)
 Sof(Cu1)=Sof(Cu2)=Sof(N3)=Sof(N4)=Sof(N1)=Sof(N2)=Sof(C11)=Sof(H11)=Sof(C12)=
 Sof(H12)=Sof(C2)=Sof(H2)=Sof(C7)=Sof(H7)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C11A(H11A), C12A(H12A)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C2A(H2A), C7A(H7A)
;
_atom_sites_solution_hydrogens   geom
_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 0.65833(3) 0.39446(3) 0.45594(3) 0.01423(8) Uani 0.8775(9) 1 d . . P A 1
Cu2 Cu 0.29015(3) 0.32249(3) 0.44267(3) 0.01423(8) Uani 0.8775(9) 1 d . . P A 1
Cu1A Cu 0.7403(3) 0.5180(3) 0.6329(2) 0.0210(6) Uani 0.1225(9) 1 d . . P A 2
Cu2A Cu 0.6271(3) 0.5647(3) 0.3833(2) 0.0216(6) Uani 0.1225(9) 1 d . . P A 2
F1 F 0.86914(19) 0.20354(19) 0.55268(16) 0.0323(4) Uani 1 1 d . . . . .
F2 F 0.97105(18) 0.30657(19) 0.76145(17) 0.0348(4) Uani 1 1 d . . . . .
F3 F 0.88774(18) 0.06628(18) 0.69926(16) 0.0292(3) Uani 1 1 d . . . . .
F4 F 0.2990(2) 0.0001(2) 0.74853(18) 0.0370(4) Uani 1 1 d . . . . .
F5 F 0.3072(2) 0.2311(2) 0.77186(15) 0.0325(4) Uani 1 1 d . . . . .
F6 F 0.15661(17) 0.08203(19) 0.57981(15) 0.0301(3) Uani 1 1 d . . . . .
F7 F 0.6432(2) 0.4386(2) 0.0954(2) 0.0520(5) Uani 1 1 d . . . . .
F8 F 0.73032(17) 0.30325(19) 0.23215(14) 0.0290(3) Uani 1 1 d . . . . .
F9 F 0.5714(2) 0.2007(2) 0.02528(17) 0.0455(5) Uani 1 1 d . . . . .
F10 F -0.03022(17) 0.14495(18) 0.18082(15) 0.0289(3) Uani 1 1 d . . . . .
F11 F -0.06795(18) 0.1314(2) -0.02468(15) 0.0330(4) Uani 1 1 d . . . . .
F12 F -0.02192(18) 0.34181(18) 0.09997(16) 0.0310(3) Uani 1 1 d . . . . .
N3 N 0.4672(2) 0.3157(2) 0.2804(2) 0.0162(4) Uani 0.8775(9) 1 d D . P A 1
N4 N 0.3126(2) 0.2912(2) 0.27415(19) 0.0155(4) Uani 0.8775(9) 1 d D . P A 1
N1 N 0.5983(2) 0.2571(2) 0.56047(19) 0.0159(4) Uani 0.8775(9) 1 d D . P A 1
N2 N 0.4492(2) 0.2359(2) 0.56420(19) 0.0150(4) Uani 0.8775(9) 1 d D . P A 1
N1A N 0.6371(18) 0.3092(10) 0.6354(12) 0.021(3) Uani 0.1225(9) 1 d D U P A 2
N2A N 0.4873(18) 0.2927(7) 0.6398(12) 0.022(3) Uani 0.1225(9) 1 d D U P A 2
N3A N 0.461(2) 0.3903(12) 0.2517(10) 0.023(3) Uani 0.1225(9) 1 d D U P A 2
N4A N 0.3058(16) 0.3651(10) 0.2451(9) 0.023(3) Uani 0.1225(9) 1 d D U P A 2
C1 C 0.6823(2) 0.1835(2) 0.64786(19) 0.0189(4) Uani 1 1 d D . . . .
C3 C 0.4460(2) 0.1506(2) 0.6549(2) 0.0188(4) Uani 1 1 d D . . . .
C4 C 0.8522(3) 0.1894(3) 0.6658(3) 0.0234(5) Uani 1 1 d . . . . .
C5 C 0.3019(3) 0.1145(3) 0.6883(2) 0.0235(5) Uani 1 1 d . . . . .
C6 C 0.4485(3) 0.2869(2) 0.1525(2) 0.0207(5) Uani 1 1 d D . . . .
C8 C 0.2025(3) 0.2471(2) 0.1420(2) 0.0206(5) Uani 1 1 d D . . . .
C9 C 0.5981(3) 0.3074(3) 0.1257(2) 0.0237(5) Uani 1 1 d . . . . .
C10 C 0.0208(3) 0.2159(3) 0.1000(2) 0.0224(5) Uani 1 1 d . . . . .
C11 C 0.8653(3) 0.5587(3) 0.5742(3) 0.0185(5) Uani 0.8775(9) 1 d . . P A 1
H11 H 0.976977 0.563850 0.643895 0.022 Uiso 0.8775(9) 1 calc R . P A 1
C12 C 0.8106(3) 0.5829(3) 0.4566(3) 0.0176(5) Uani 0.8775(9) 1 d . . P A 1
H12 H 0.862011 0.615166 0.395894 0.021 Uiso 0.8775(9) 1 calc R . P A 1
C11A C 0.825(2) 0.515(3) 0.498(2) 0.018(3) Uani 0.1225(9) 1 d . U P A 2
H11A H 0.896891 0.461495 0.478390 0.021 Uiso 0.1225(9) 1 calc R . P A 2
C12A C 0.847(2) 0.644(2) 0.543(2) 0.020(3) Uani 0.1225(9) 1 d . U P A 2
H12A H 0.941922 0.738858 0.574408 0.024 Uiso 0.1225(9) 1 calc R . P A 2
C2 C 0.5911(3) 0.1137(3) 0.7097(2) 0.0164(5) Uani 0.8775(9) 1 d D U P A 1
H2 H 0.620618 0.054528 0.774386 0.020 Uiso 0.8775(9) 1 calc R . P A 1
C7 C 0.2831(3) 0.2415(3) 0.0614(2) 0.0182(5) Uani 0.8775(9) 1 d D U P A 1
H7 H 0.236116 0.213171 -0.033730 0.022 Uiso 0.8775(9) 1 calc R . P A 1
C2A C 0.5601(6) 0.0776(7) 0.6611(9) 0.0184(16) Uani 0.1225(9) 1 d D U P A 2
H2A H 0.555619 -0.021638 0.671873 0.022 Uiso 0.1225(9) 1 calc R . P A 2
C7A C 0.2872(5) 0.1941(8) 0.0798(7) 0.0198(17) Uani 0.1225(9) 1 d D U P A 2
H7A H 0.244574 0.113011 0.004793 0.024 Uiso 0.1225(9) 1 calc R . P A 2


_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 2.6469(6) 2_666 ?
Cu1 N3 1.952(2) . ?
Cu1 N1 1.949(2) . ?
Cu1 C11 1.982(3) . ?
Cu1 C12 1.975(3) . ?
Cu2 N4 1.970(2) . ?
Cu2 N2 1.972(2) . ?
Cu2 C11 1.996(3) 2_666 ?
Cu2 C12 1.993(2) 2_666 ?
Cu1A Cu2A 2.676(3) . ?
Cu1A N1A 1.976(12) . ?
Cu1A N4A 1.909(13) 2_666 ?
Cu1A C11A 1.96(2) . ?
Cu1A C12A 1.96(2) . ?
Cu2A N2A 1.885(12) 2_666 ?
Cu2A N3A 1.926(12) . ?
Cu2A C11A 1.97(2) . ?
Cu2A C12A 1.99(2) . ?
F1 C4 1.345(3) . ?
F2 C4 1.343(3) . ?
F3 C4 1.333(3) . ?
F4 C5 1.326(3) . ?
F5 C5 1.349(3) . ?
F6 C5 1.337(3) . ?
F7 C9 1.328(3) . ?
F8 C9 1.334(3) . ?
F9 C9 1.328(3) . ?
F10 C10 1.335(3) . ?
F11 C10 1.337(3) . ?
F12 C10 1.343(3) . ?
N3 N4 1.362(3) . ?
N3 C6 1.355(3) . ?
N4 C8 1.361(3) . ?
N1 N2 1.361(3) . ?
N1 C1 1.352(2) . ?
N2 C3 1.356(2) . ?
N1A N2A 1.38(2) . ?
N1A C1 1.354(4) . ?
N2A C3 1.349(4) . ?
N3A N4A 1.36(2) . ?
N3A C6 1.351(4) . ?
N4A C8 1.350(4) . ?
C1 C4 1.488(3) . ?
C1 C2 1.377(3) . ?
C1 C2A 1.379(4) . ?
C3 C5 1.492(3) . ?
C3 C2 1.383(3) . ?
C3 C2A 1.380(4) . ?
C6 C9 1.498(3) . ?
C6 C7 1.381(3) . ?
C6 C7A 1.379(4) . ?
C8 C10 1.494(3) . ?
C8 C7 1.380(3) . ?
C8 C7A 1.379(4) . ?
C11 H11 1.0000 . ?
C11 C12 1.269(4) . ?
C12 H12 1.0000 . ?
C11A H11A 1.0000 . ?
C11A C12A 1.21(3) . ?
C12A H12A 1.0000 . ?
C2 H2 0.9500 . ?
C7 H7 0.9500 . ?
C2A H2A 0.9500 . ?
C7A H7A 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
N3 Cu1 Cu2 113.06(6) . 2_666 ?
N3 Cu1 C11 147.72(10) . . ?
N3 Cu1 C12 110.48(10) . . ?
N1 Cu1 Cu2 113.22(6) . 2_666 ?
N1 Cu1 N3 101.71(8) . . ?
N1 Cu1 C11 110.01(10) . . ?
N1 Cu1 C12 147.29(10) . . ?
C11 Cu1 Cu2 48.52(7) . 2_666 ?
C12 Cu1 Cu2 48.46(7) . 2_666 ?
C12 Cu1 C11 37.41(12) . . ?
N4 Cu2 Cu1 114.07(6) . 2_666 ?
N4 Cu2 N2 104.37(8) . . ?
N4 Cu2 C11 109.28(10) . 2_666 ?
N4 Cu2 C12 146.32(10) . 2_666 ?
N2 Cu2 Cu1 112.74(6) . 2_666 ?
N2 Cu2 C11 146.02(10) . 2_666 ?
N2 Cu2 C12 109.03(10) . 2_666 ?
C11 Cu2 Cu1 48.06(8) 2_666 2_666 ?
C12 Cu2 Cu1 47.87(8) 2_666 2_666 ?
C12 Cu2 C11 37.10(11) 2_666 2_666 ?
N1A Cu1A Cu2A 111.4(4) . . ?
N4A Cu1A Cu2A 115.1(4) 2_666 . ?
N4A Cu1A N1A 103.9(5) 2_666 . ?
N4A Cu1A C11A 147.2(8) 2_666 . ?
N4A Cu1A C12A 111.3(7) 2_666 . ?
C11A Cu1A Cu2A 47.2(6) . . ?
C11A Cu1A N1A 108.5(8) . . ?
C11A Cu1A C12A 36.0(9) . . ?
C12A Cu1A Cu2A 47.8(6) . . ?
C12A Cu1A N1A 144.4(7) . . ?
N2A Cu2A Cu1A 113.1(4) 2_666 . ?
N2A Cu2A N3A 102.0(5) 2_666 . ?
N2A Cu2A C11A 146.1(8) 2_666 . ?
N2A Cu2A C12A 110.7(7) 2_666 . ?
N3A Cu2A Cu1A 112.8(4) . . ?
N3A Cu2A C11A 111.0(8) . . ?
N3A Cu2A C12A 146.3(7) . . ?
C11A Cu2A Cu1A 46.8(6) . . ?
C11A Cu2A C12A 35.6(9) . . ?
C12A Cu2A Cu1A 46.8(6) . . ?
N4 N3 Cu1 118.26(14) . . ?
C6 N3 Cu1 134.29(16) . . ?
C6 N3 N4 107.25(18) . . ?
N3 N4 Cu2 118.92(14) . . ?
C8 N4 Cu2 133.95(15) . . ?
C8 N4 N3 107.13(18) . . ?
N2 N1 Cu1 118.85(14) . . ?
C1 N1 Cu1 133.50(15) . . ?
C1 N1 N2 107.22(18) . . ?
N1 N2 Cu2 118.12(14) . . ?
C3 N2 Cu2 134.64(15) . . ?
C3 N2 N1 107.21(17) . . ?
N2A N1A Cu1A 110.7(3) . . ?
C1 N1A Cu1A 136.7(10) . . ?
C1 N1A N2A 112.1(10) . . ?
C3 N2A Cu2A 131.9(10) . 2_666 ?
C3 N2A N1A 101.8(9) . . ?
N4A N3A Cu2A 114.9(4) . . ?
C6 N3A Cu2A 137.6(11) . . ?
C6 N3A N4A 107.3(10) . . ?
C8 N4A Cu1A 129.7(10) . 2_666 ?
C8 N4A N3A 107.4(9) . . ?
N1 C1 C4 118.87(19) . . ?
N1 C1 C2 111.38(18) . . ?
N1A C1 C4 118.9(7) . . ?
N1A C1 C2A 108.0(7) . . ?
C2 C1 C4 129.74(19) . . ?
C2A C1 C4 132.2(3) . . ?
N2 C3 C5 120.44(18) . . ?
N2 C3 C2 110.99(18) . . ?
N2A C3 C5 112.0(7) . . ?
N2A C3 C2A 114.8(7) . . ?
C2 C3 C5 128.5(2) . . ?
C2A C3 C5 131.9(3) . . ?
F1 C4 C1 111.34(19) . . ?
F2 C4 F1 105.8(2) . . ?
F2 C4 C1 112.8(2) . . ?
F3 C4 F1 107.66(19) . . ?
F3 C4 F2 107.09(19) . . ?
F3 C4 C1 111.76(19) . . ?
F4 C5 F5 107.1(2) . . ?
F4 C5 F6 108.6(2) . . ?
F4 C5 C3 111.25(19) . . ?
F5 C5 C3 111.9(2) . . ?
F6 C5 F5 105.40(19) . . ?
F6 C5 C3 112.38(19) . . ?
N3 C6 C9 120.07(19) . . ?
N3 C6 C7 111.27(19) . . ?
N3A C6 C9 116.8(7) . . ?
N3A C6 C7A 111.0(7) . . ?
C7 C6 C9 128.7(2) . . ?
C7A C6 C9 131.2(3) . . ?
N4 C8 C10 120.70(19) . . ?
N4 C8 C7 111.06(19) . . ?
N4A C8 C10 116.7(7) . . ?
N4A C8 C7A 111.0(7) . . ?
C7 C8 C10 128.2(2) . . ?
C7A C8 C10 131.2(3) . . ?
F7 C9 F8 105.9(2) . . ?
F7 C9 F9 107.9(2) . . ?
F7 C9 C6 112.2(2) . . ?
F8 C9 C6 112.16(19) . . ?
F9 C9 F8 106.8(2) . . ?
F9 C9 C6 111.6(2) . . ?
F10 C10 F11 107.7(2) . . ?
F10 C10 F12 106.24(19) . . ?
F10 C10 C8 112.61(18) . . ?
F11 C10 F12 106.84(19) . . ?
F11 C10 C8 110.90(19) . . ?
F12 C10 C8 112.2(2) . . ?
Cu1 C11 Cu2 83.42(9) . 2_666 ?
Cu1 C11 H11 134.8 . . ?
Cu2 C11 H11 134.8 2_666 . ?
C12 C11 Cu1 71.00(18) . . ?
C12 C11 Cu2 71.34(16) . 2_666 ?
C12 C11 H11 134.8 . . ?
Cu1 C12 Cu2 83.67(9) . 2_666 ?
Cu1 C12 H12 134.6 . . ?
Cu2 C12 H12 134.6 2_666 . ?
C11 C12 Cu1 71.59(18) . . ?
C11 C12 Cu2 71.56(16) . 2_666 ?
C11 C12 H12 134.6 . . ?
Cu1A C11A Cu2A 86.0(7) . . ?
Cu1A C11A H11A 133.6 . . ?
Cu2A C11A H11A 133.6 . . ?
C12A C11A Cu1A 72.1(14) . . ?
C12A C11A Cu2A 73.1(14) . . ?
C12A C11A H11A 133.6 . . ?
Cu1A C12A Cu2A 85.4(8) . . ?
Cu1A C12A H12A 134.1 . . ?
Cu2A C12A H12A 134.1 . . ?
C11A C12A Cu1A 71.9(14) . . ?
C11A C12A Cu2A 71.3(14) . . ?
C11A C12A H12A 134.1 . . ?
C1 C2 C3 103.19(19) . . ?
C1 C2 H2 128.4 . . ?
C3 C2 H2 128.4 . . ?
C6 C7 H7 128.4 . . ?
C8 C7 C6 103.3(2) . . ?
C8 C7 H7 128.4 . . ?
C1 C2A C3 103.3(4) . . ?
C1 C2A H2A 128.4 . . ?
C3 C2A H2A 128.4 . . ?
C6 C7A H7A 128.3 . . ?
C8 C7A C6 103.4(4) . . ?
C8 C7A H7A 128.3 . . ?

_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_rad640_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1934985'
loop_
_audit_author_name
_audit_author_address
'Rasika Dias'
;The University of Texas at Arlington
United States of America
;
_audit_update_record             
;
2019-06-18 deposited with the CCDC.	2019-09-05 downloaded from the CCDC.
;
_audit_creation_date             2018-06-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 Cu2 F12 N4'
_chemical_formula_sum            'C18 H12 Cu2 F12 N4'
_chemical_formula_weight         639.40
_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                   10.4189(5)
_cell_length_b                   10.4808(5)
_cell_length_c                   12.2860(6)
_cell_angle_alpha                92.068(2)
_cell_angle_beta                 110.195(2)
_cell_angle_gamma                115.740(2)
_cell_volume                     1106.40(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8933
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.72
_cell_measurement_theta_min      3.15
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.630
_exptl_absorpt_coefficient_mu    2.037
_exptl_absorpt_correction_T_max  0.3394
_exptl_absorpt_correction_T_min  0.2702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0675 before and 0.0445 after correction. The Ratio of minimum to maximum transmission is 0.7961. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhomboid
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.971
_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       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14149
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.722
_diffrn_reflns_theta_min         3.152
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  
'Bruker D8 Quest with a Photon 100 CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6165
_reflns_number_total             7904
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.901
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         7904
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.020
_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)+(0.0426P)²+1.0689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0963
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C15(H15)
;
_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 0.72525(3) 0.25016(3) 0.61042(2) 0.01629(6) Uani 1 1 d . . . . .
Cu2 Cu 0.40464(3) 0.79359(3) 0.19142(2) 0.01640(6) Uani 1 1 d . . . . .
F1 F 0.9680(2) 0.15096(18) 0.60228(15) 0.0388(4) Uani 1 1 d . . . . .
F2 F 0.7840(2) -0.0653(2) 0.51888(15) 0.0442(4) Uani 1 1 d . . . . .
F3 F 0.9941(2) -0.0292(2) 0.66317(18) 0.0513(5) Uani 1 1 d . . . . .
F4 F 0.6901(2) 0.06077(16) 1.01216(13) 0.0366(4) Uani 1 1 d . . . . .
F5 F 0.5434(2) -0.15606(18) 0.91083(17) 0.0525(5) Uani 1 1 d . . . . .
F6 F 0.7810(3) -0.0884(3) 1.02328(19) 0.0618(6) Uani 1 1 d . . . . .
F7 F 0.30299(19) 0.40016(19) 0.01624(14) 0.0377(4) Uani 1 1 d . . . . .
F8 F 0.2607(2) 0.57383(17) -0.04235(14) 0.0351(3) Uani 1 1 d . . . . .
F9 F 0.07310(18) 0.35415(17) -0.10087(13) 0.0360(3) Uani 1 1 d . . . . .
F10 F 0.0657(2) 0.3361(2) 0.40164(17) 0.0500(5) Uani 1 1 d . . . . .
F11 F -0.0165(2) 0.49055(17) 0.37173(17) 0.0416(4) Uani 1 1 d . . . . .
F12 F -0.1506(2) 0.27970(18) 0.25518(16) 0.0488(5) Uani 1 1 d . . . . .
N1 N 0.7601(2) 0.11416(18) 0.70851(15) 0.0185(3) Uani 1 1 d . . . . .
N2 N 0.7046(2) 0.09572(18) 0.79483(15) 0.0184(3) Uani 1 1 d . . . . .
N3 N 0.24389(19) 0.59587(18) 0.17644(15) 0.0164(3) Uani 1 1 d . . . . .
N4 N 0.19042(19) 0.57745(18) 0.26398(15) 0.0168(3) Uani 1 1 d . . . . .
C1 C 0.8251(2) 0.0274(2) 0.71151(19) 0.0207(4) Uani 1 1 d . . . . .
C2 C 0.8130(3) -0.0499(2) 0.8001(2) 0.0257(4) Uani 1 1 d . . . . .
H2 H 0.848460 -0.118700 0.821391 0.031 Uiso 1 1 calc R . . . .
C3 C 0.7362(3) -0.0019(2) 0.84978(19) 0.0217(4) Uani 1 1 d . . . . .
C4 C 0.8930(3) 0.0210(3) 0.6249(2) 0.0288(5) Uani 1 1 d . . . . .
C5 C 0.6869(3) -0.0472(2) 0.9482(2) 0.0264(4) Uani 1 1 d . . . . .
C6 C 0.6136(3) 0.1585(3) 0.4408(2) 0.0257(4) Uani 1 1 d . . . . .
H6 H 0.596(4) 0.071(4) 0.407(3) 0.038(9) Uiso 1 1 d . . . . .
C7 C 0.6109(3) 0.2733(2) 0.45179(19) 0.0228(4) Uani 1 1 d . . . . .
C8 C 0.5754(3) 0.3945(3) 0.4289(2) 0.0262(4) Uani 1 1 d . . . . .
H8A H 0.628638 0.468351 0.503965 0.031 Uiso 1 1 calc R . . . .
H8B H 0.462058 0.357264 0.403302 0.031 Uiso 1 1 calc R . . . .
C9 C 0.6249(3) 0.4673(2) 0.33409(19) 0.0227(4) Uani 1 1 d . . . . .
H9A H 0.736858 0.499530 0.356148 0.027 Uiso 1 1 calc R . . . .
H9B H 0.565435 0.396640 0.256686 0.027 Uiso 1 1 calc R . . . .
C10 C 0.5955(3) 0.5972(2) 0.32297(19) 0.0219(4) Uani 1 1 d . . . . .
H10A H 0.659224 0.669057 0.399743 0.026 Uiso 1 1 calc R . . . .
H10B H 0.484786 0.564842 0.306314 0.026 Uiso 1 1 calc R . . . .
C11 C 0.6339(2) 0.6704(2) 0.22495(19) 0.0217(4) Uani 1 1 d . . . . .
H11A H 0.744454 0.702438 0.241224 0.026 Uiso 1 1 calc R . . . .
H11B H 0.569590 0.598948 0.147955 0.026 Uiso 1 1 calc R . . . .
C12 C 0.6057(2) 0.7971(2) 0.21574(18) 0.0207(4) Uani 1 1 d . . . . .
C13 C 0.6221(3) 0.9200(2) 0.2187(2) 0.0240(4) Uani 1 1 d . . . . .
H13 H 0.668(4) 1.020(4) 0.224(3) 0.045(9) Uiso 1 1 d . . . . .
C14 C 0.1624(2) 0.4688(2) 0.09656(18) 0.0181(3) Uani 1 1 d . . . . .
C15 C 0.0540(2) 0.3656(2) 0.1300(2) 0.0218(4) Uani 1 1 d . . . . .
H15 H -0.018825 0.267606 0.089782 0.026 Uiso 1 1 calc R . . . .
C16 C 0.0771(2) 0.4399(2) 0.23693(19) 0.0192(4) Uani 1 1 d . . . . .
C17 C 0.1993(3) 0.4503(2) -0.00744(19) 0.0236(4) Uani 1 1 d . . . . .
C18 C -0.0060(3) 0.3865(2) 0.3159(2) 0.0268(4) 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 1.9716(17) . ?
Cu1 N4 1.9752(16) 2_666 ?
Cu1 C6 1.957(2) . ?
Cu1 C7 1.990(2) . ?
Cu2 N2 1.9838(17) 2_666 ?
Cu2 N3 1.9693(17) . ?
Cu2 C12 1.994(2) . ?
Cu2 C13 1.959(2) . ?
F1 C4 1.340(3) . ?
F2 C4 1.344(3) . ?
F3 C4 1.329(3) . ?
F4 C5 1.336(3) . ?
F5 C5 1.324(3) . ?
F6 C5 1.330(3) . ?
F7 C17 1.347(3) . ?
F8 C17 1.334(3) . ?
F9 C17 1.336(2) . ?
F10 C18 1.336(3) . ?
F11 C18 1.332(3) . ?
F12 C18 1.334(3) . ?
N1 N2 1.355(2) . ?
N1 C1 1.344(3) . ?
N2 C3 1.342(3) . ?
N3 N4 1.356(2) . ?
N3 C14 1.344(2) . ?
N4 C16 1.341(2) . ?
C1 C2 1.388(3) . ?
C1 C4 1.481(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(3) . ?
C3 C5 1.487(3) . ?
C6 H6 0.91(3) . ?
C6 C7 1.219(3) . ?
C7 C8 1.481(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.530(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.521(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.527(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.480(3) . ?
C12 C13 1.220(3) . ?
C13 H13 0.93(3) . ?
C14 C15 1.381(3) . ?
C14 C17 1.484(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(3) . ?
C16 C18 1.484(3) . ?

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 N4 100.29(7) . 2_666 ?
N1 Cu1 C7 146.56(8) . . ?
N4 Cu1 C7 111.41(8) 2_666 . ?
C6 Cu1 N1 112.13(9) . . ?
C6 Cu1 N4 147.31(9) . 2_666 ?
C6 Cu1 C7 35.98(9) . . ?
N2 Cu2 C12 147.72(8) 2_666 . ?
N3 Cu2 N2 99.78(7) . 2_666 ?
N3 Cu2 C12 110.87(8) . . ?
C13 Cu2 N2 112.63(9) . 2_666 ?
C13 Cu2 N3 146.77(9) . . ?
C13 Cu2 C12 35.94(9) . . ?
N2 N1 Cu1 116.37(13) . . ?
C1 N1 Cu1 135.92(15) . . ?
C1 N1 N2 107.70(17) . . ?
N1 N2 Cu2 116.88(13) . 2_666 ?
C3 N2 Cu2 135.42(15) . 2_666 ?
C3 N2 N1 107.66(17) . . ?
N4 N3 Cu2 115.71(12) . . ?
C14 N3 Cu2 136.71(14) . . ?
C14 N3 N4 107.48(16) . . ?
N3 N4 Cu1 117.65(12) . 2_666 ?
C16 N4 Cu1 134.19(14) . 2_666 ?
C16 N4 N3 107.90(16) . . ?
N1 C1 C2 110.87(19) . . ?
N1 C1 C4 120.3(2) . . ?
C2 C1 C4 128.8(2) . . ?
C1 C2 H2 128.6 . . ?
C1 C2 C3 102.83(19) . . ?
C3 C2 H2 128.6 . . ?
N2 C3 C2 110.9(2) . . ?
N2 C3 C5 120.44(19) . . ?
C2 C3 C5 128.6(2) . . ?
F1 C4 F2 105.5(2) . . ?
F1 C4 C1 112.76(19) . . ?
F2 C4 C1 112.2(2) . . ?
F3 C4 F1 107.1(2) . . ?
F3 C4 F2 107.2(2) . . ?
F3 C4 C1 111.7(2) . . ?
F4 C5 C3 112.03(18) . . ?
F5 C5 F4 106.0(2) . . ?
F5 C5 F6 107.5(2) . . ?
F5 C5 C3 113.2(2) . . ?
F6 C5 F4 106.6(2) . . ?
F6 C5 C3 111.1(2) . . ?
Cu1 C6 H6 126(2) . . ?
C7 C6 Cu1 73.47(14) . . ?
C7 C6 H6 161(2) . . ?
C6 C7 Cu1 70.55(14) . . ?
C6 C7 C8 163.4(2) . . ?
C8 C7 Cu1 125.75(16) . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C7 C8 C9 113.57(18) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 C8 110.03(17) . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C9 C10 C11 113.00(17) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C10 112.37(17) . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C11 C12 Cu2 125.30(15) . . ?
C13 C12 Cu2 70.45(14) . . ?
C13 C12 C11 163.9(2) . . ?
Cu2 C13 H13 125(2) . . ?
C12 C13 Cu2 73.61(14) . . ?
C12 C13 H13 161(2) . . ?
N3 C14 C15 110.93(18) . . ?
N3 C14 C17 120.88(18) . . ?
C15 C14 C17 128.09(18) . . ?
C14 C15 H15 128.4 . . ?
C14 C15 C16 103.20(17) . . ?
C16 C15 H15 128.4 . . ?
N4 C16 C15 110.49(18) . . ?
N4 C16 C18 120.75(18) . . ?
C15 C16 C18 128.75(19) . . ?
F7 C17 C14 111.70(19) . . ?
F8 C17 F7 106.18(19) . . ?
F8 C17 F9 107.55(19) . . ?
F8 C17 C14 113.09(18) . . ?
F9 C17 F7 106.23(18) . . ?
F9 C17 C14 111.67(18) . . ?
F10 C18 C16 112.5(2) . . ?
F11 C18 F10 105.7(2) . . ?
F11 C18 F12 107.1(2) . . ?
F11 C18 C16 112.30(18) . . ?
F12 C18 F10 107.4(2) . . ?
F12 C18 C16 111.5(2) . . ?

_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_rad691a_a
_database_code_depnum_ccdc_archive 'CCDC 1934982'
loop_
_audit_author_name
_audit_author_address
'Rasika Dias'
;The University of Texas at Arlington
United States of America
;
_audit_update_record             
;
2019-06-18 deposited with the CCDC.	2019-09-05 downloaded from the CCDC.
;
_audit_creation_date             2019-06-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H4 Br2 Cu2 F12 N4, C7 H8'
_chemical_formula_sum            'C21 H12 Br2 Cu2 F12 N4'
_chemical_formula_weight         835.25
_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'
Br Br -0.2901 2.4595 '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      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   17.0895(6)
_cell_length_b                   15.2842(5)
_cell_length_c                   10.1011(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2638.40(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.52
_cell_measurement_theta_min      3.34
_shelx_estimated_absorpt_T_max   0.482
_shelx_estimated_absorpt_T_min   0.383
_exptl_absorpt_coefficient_mu    4.746
_exptl_absorpt_correction_T_max  0.3455
_exptl_absorpt_correction_T_min  0.2520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1039 before and 0.0704 after correction. The Ratio of minimum to maximum transmission is 0.7294. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.103
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       parallelpipeds
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21352
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.142
_diffrn_reflns_theta_min         3.343
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  
'Bruker D8 Quest with a Photon 100 CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                4886
_reflns_number_total             5139
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.023(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         5139
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0218
_refine_ls_restrained_S_all      1.063
_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)+(0.0213P)²+0.0218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0501
_refine_ls_wR_factor_ref         0.0511
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.977(8)
 0.023(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C10-C11 \\sim C11-C12 \\sim C12-C13 \\sim C13-C14 \\sim C14-C15 \\sim C15-C10
 with sigma of 0.02
 C10-C14 \\sim C10-C12 \\sim C15-C13 \\sim C11-C15 \\sim C12-C14 \\sim C11-C13
 with sigma of 0.04
 C9-C15 \\sim C9-C11
 with sigma of 0.04
4. Restrained planarity
 C9, C10, C11, C12, C13, C14, C15
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
6. Rigid body (RIGU) restrains
 C9, C10, C11, C12, C13, C14, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Fixed Sof: C9(0.5) H9A(0.5) H9B(0.5) H9C(0.5) C10(0.5) C11(0.5) H11(0.5)
 C12(0.5) H12(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5) C15(0.5) H15(0.5)
8.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
8.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_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
Br1 Br 0.500000 -0.09288(2) 0.39211(4) 0.02586(8) Uani 1 2 d S T P . .
Br2 Br 0.500000 0.53397(2) 0.23595(3) 0.01999(7) Uani 1 2 d S T P . .
Cu Cu 0.40637(2) 0.25276(2) 0.61253(3) 0.01320(5) Uani 1 1 d . . . . .
F1 F 0.30732(10) 0.11924(12) 0.4881(3) 0.0471(6) Uani 1 1 d . . . . .
F2 F 0.32546(11) 0.00447(19) 0.6008(2) 0.0557(7) Uani 1 1 d . . . . .
F3 F 0.33408(10) 0.00025(18) 0.3910(3) 0.0504(6) Uani 1 1 d . . . . .
F4 F 0.33140(10) 0.48745(16) 0.4782(3) 0.0509(6) Uani 1 1 d . . . . .
F5 F 0.30555(9) 0.35457(12) 0.4296(2) 0.0355(4) Uani 1 1 d . . . . .
F6 F 0.33209(10) 0.44582(14) 0.2769(2) 0.0372(4) Uani 1 1 d . . . . .
N1 N 0.46036(10) 0.14512(11) 0.55635(19) 0.0139(3) Uani 1 1 d . . . . .
N2 N 0.46021(10) 0.33715(11) 0.49592(18) 0.0127(3) Uani 1 1 d . . . . .
C1 C 0.43593(12) 0.06847(14) 0.5055(2) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.500000 0.01697(19) 0.4715(3) 0.0158(5) Uani 1 2 d S T P . .
C3 C 0.35087(13) 0.04762(15) 0.4966(2) 0.0189(4) Uani 1 1 d . . . . .
C4 C 0.43591(11) 0.40004(13) 0.4124(2) 0.0135(3) Uani 1 1 d . . . . .
C5 C 0.500000 0.44178(19) 0.3566(3) 0.0127(5) Uani 1 2 d S T P . .
C6 C 0.35132(12) 0.42152(15) 0.3985(3) 0.0187(4) Uani 1 1 d . . . . .
C7 C 0.33492(15) 0.2316(2) 0.7617(3) 0.0276(5) Uani 1 1 d . . . . .
H7 H 0.314821 0.187728 0.819060 0.033 Uiso 1 1 calc R . . . .
C8 C 0.33230(15) 0.30985(18) 0.7351(3) 0.0273(5) Uani 1 1 d . . . . .
H8 H 0.309090 0.364119 0.758746 0.033 Uiso 1 1 calc R . . . .
C9 C 0.6303(5) 0.2302(6) 0.1608(9) 0.0449(18) Uani 0.5 1 d D U . A -1
H9A H 0.644858 0.177574 0.111158 0.067 Uiso 0.5 1 calc GR . . A -1
H9B H 0.643033 0.222001 0.254587 0.067 Uiso 0.5 1 calc GR . . A -1
H9C H 0.659368 0.280537 0.126167 0.067 Uiso 0.5 1 calc GR . . A -1
C10 C 0.5438(4) 0.2464(3) 0.1462(5) 0.0271(11) Uani 0.5 1 d D U . A -1
C11 C 0.5188(3) 0.3123(3) 0.0611(6) 0.0254(11) Uani 0.5 1 d D U . A -1
H11 H 0.555920 0.347351 0.015426 0.030 Uiso 0.5 1 calc R . . A -1
C12 C 0.4392(4) 0.3267(4) 0.0434(6) 0.0308(12) Uani 0.5 1 d D U . A -1
H12 H 0.422171 0.372036 -0.014230 0.037 Uiso 0.5 1 calc R . . A -1
C13 C 0.3846(3) 0.2761(4) 0.1083(6) 0.0316(10) Uani 0.5 1 d D U . A -1
H13 H 0.330369 0.286274 0.094532 0.038 Uiso 0.5 1 calc R . . A -1
C14 C 0.4085(5) 0.2107(5) 0.1931(7) 0.0354(13) Uani 0.5 1 d D U . A -1
H14 H 0.371357 0.174798 0.237146 0.043 Uiso 0.5 1 calc R . . A -1
C15 C 0.4887(6) 0.1983(4) 0.2127(5) 0.0340(19) Uani 0.5 1 d D U . A -1
H15 H 0.505579 0.155232 0.274126 0.041 Uiso 0.5 1 calc R . . A -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
Br1 C2 1.860(3) . ?
Br2 C5 1.863(3) . ?
Cu N1 1.9697(18) . ?
Cu N2 1.9742(18) . ?
Cu C7 1.966(3) . ?
Cu C8 1.974(3) . ?
F1 C3 1.326(3) . ?
F2 C3 1.316(3) . ?
F3 C3 1.321(3) . ?
F4 C6 1.334(3) . ?
F5 C6 1.326(3) . ?
F6 C6 1.324(3) . ?
N1 N1 1.355(3) 4_655 ?
N1 C1 1.346(3) . ?
N2 N2 1.360(3) 4_655 ?
N2 C4 1.344(3) . ?
C1 C2 1.392(3) . ?
C1 C3 1.491(3) . ?
C4 C5 1.387(3) . ?
C4 C6 1.489(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.227(4) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C10 1.506(10) . ?
C10 C11 1.392(7) . ?
C10 C15 1.370(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(9) . ?
C12 H12 0.9500 . ?
C12 C13 1.378(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.397(12) . ?
C15 H15 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 Cu N2 98.94(8) . . ?
N1 Cu C8 148.24(10) . . ?
C7 Cu N1 111.96(10) . . ?
C7 Cu N2 148.68(11) . . ?
C7 Cu C8 36.29(11) . . ?
C8 Cu N2 112.60(10) . . ?
N1 N1 Cu 117.93(5) 4_655 . ?
C1 N1 Cu 133.78(14) . . ?
C1 N1 N1 108.07(11) . 4_655 ?
N2 N2 Cu 117.78(5) 4_655 . ?
C4 N2 Cu 134.22(14) . . ?
C4 N2 N2 107.99(11) . 4_655 ?
N1 C1 C2 110.04(19) . . ?
N1 C1 C3 120.77(19) . . ?
C2 C1 C3 129.1(2) . . ?
C1 C2 Br1 128.09(13) . . ?
C1 C2 Br1 128.09(13) 4_655 . ?
C1 C2 C1 103.8(3) . 4_655 ?
F1 C3 C1 112.00(19) . . ?
F2 C3 F1 106.3(2) . . ?
F2 C3 F3 107.4(3) . . ?
F2 C3 C1 112.4(2) . . ?
F3 C3 F1 106.2(2) . . ?
F3 C3 C1 112.2(2) . . ?
N2 C4 C5 109.87(18) . . ?
N2 C4 C6 121.11(19) . . ?
C5 C4 C6 128.8(2) . . ?
C4 C5 Br2 127.86(12) 4_655 . ?
C4 C5 Br2 127.86(12) . . ?
C4 C5 C4 104.3(2) 4_655 . ?
F4 C6 C4 110.95(18) . . ?
F5 C6 F4 106.8(2) . . ?
F5 C6 C4 112.34(19) . . ?
F6 C6 F4 106.5(2) . . ?
F6 C6 F5 106.9(2) . . ?
F6 C6 C4 113.0(2) . . ?
Cu C7 H7 143.9 . . ?
C8 C7 Cu 72.19(17) . . ?
C8 C7 H7 143.9 . . ?
Cu C8 H8 144.2 . . ?
C7 C8 Cu 71.52(16) . . ?
C7 C8 H8 144.2 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
C11 C10 C9 118.8(6) . . ?
C15 C10 C9 122.6(7) . . ?
C15 C10 C11 118.6(6) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.7(5) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(6) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.5(6) . . ?
C15 C14 H14 120.8 . . ?
C10 C15 C14 122.2(5) . . ?
C10 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.977(8)
2 0.023(8)
####################################################################### 
# 
# 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_rad518_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1934984'
loop_
_audit_author_name
_audit_author_address
'Rasika Dias'
;The University of Texas at Arlington
United States of America
;
_audit_update_record             
;
2019-06-18 deposited with the CCDC.	2019-09-05 downloaded from the CCDC.
;
_audit_creation_date             2017-06-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 Cu2 F12 N4'
_chemical_formula_sum            'C19 H14 Cu2 F12 N4'
_chemical_formula_weight         653.42
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0850(4)
_cell_length_b                   14.3949(5)
_cell_length_c                   14.0223(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.7460(10)
_cell_angle_gamma                90
_cell_volume                     2237.31(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.21
_cell_measurement_theta_min      3.18
_shelx_estimated_absorpt_T_max   0.765
_shelx_estimated_absorpt_T_min   0.622
_exptl_absorpt_coefficient_mu    2.017
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0632 before and 0.0467 after correction. The Ratio of minimum to maximum transmission is 0.8549. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.940
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       parallelpipeds
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            36294
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.230
_diffrn_reflns_theta_min         2.830
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  
'Bruker D8 Quest with a Photon 100 CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7340
_reflns_number_total             8553
_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.
;
# start Validation Reply Form
_vrf_PLAT934_rad518_0m_a         
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          3 Check 
RESPONSE: these reflections were partially obstructed by hardware
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         8553
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.060
_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)+(0.0367P)²+1.0853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0740
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(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)
;
_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 0.28902(2) 0.51993(2) 0.41231(2) 0.01289(4) Uani 1 1 d . . . . .
Cu2 Cu 0.45342(2) 0.52273(2) 0.23199(2) 0.01332(4) Uani 1 1 d . . . . .
F1 F 0.36850(11) 0.81600(7) 0.56552(7) 0.0375(2) Uani 1 1 d . . . . .
F2 F 0.36397(10) 0.67114(7) 0.60169(6) 0.0313(2) Uani 1 1 d . . . . .
F3 F 0.22215(8) 0.72934(8) 0.51518(7) 0.0358(2) Uani 1 1 d . . . . .
F4 F 0.65142(11) 0.82183(7) 0.24992(10) 0.0470(3) Uani 1 1 d . . . . .
F5 F 0.71417(9) 0.68161(9) 0.25254(10) 0.0490(3) Uani 1 1 d . . . . .
F6 F 0.56964(11) 0.71980(11) 0.15829(8) 0.0503(3) Uani 1 1 d . . . . .
F7 F 0.00582(9) 0.59436(7) 0.39137(8) 0.0364(2) Uani 1 1 d . . . . .
F8 F -0.01544(9) 0.44802(7) 0.37737(8) 0.0337(2) Uani 1 1 d . . . . .
F9 F -0.11401(8) 0.53874(10) 0.28375(9) 0.0443(3) Uani 1 1 d . . . . .
F10 F 0.34470(10) 0.59227(7) 0.02750(6) 0.0322(2) Uani 1 1 d . . . . .
F11 F 0.31395(10) 0.44677(6) 0.01319(6) 0.03021(19) Uani 1 1 d . . . . .
F12 F 0.17611(10) 0.54254(9) -0.03180(7) 0.0397(2) Uani 1 1 d . . . . .
N1 N 0.38941(9) 0.63270(7) 0.39443(7) 0.01386(17) Uani 1 1 d . . . . .
N2 N 0.46220(9) 0.63361(7) 0.31736(7) 0.01465(17) Uani 1 1 d . . . . .
N3 N 0.20666(9) 0.52069(7) 0.28753(7) 0.01386(17) Uani 1 1 d . . . . .
N4 N 0.27794(9) 0.52096(7) 0.20995(7) 0.01425(17) Uani 1 1 d . . . . .
C1 C 0.41000(11) 0.71153(8) 0.44348(9) 0.0170(2) Uani 1 1 d . . . . .
C2 C 0.49584(12) 0.76570(9) 0.39924(10) 0.0205(2) Uani 1 1 d . . . . .
H2 H 0.5265 0.8246 0.4182 0.025 Uiso 1 1 calc R . . . .
C3 C 0.52595(11) 0.71296(9) 0.32061(9) 0.0181(2) Uani 1 1 d . . . . .
C4 C 0.34086(13) 0.73162(10) 0.53105(9) 0.0220(2) Uani 1 1 d . . . . .
C5 C 0.61503(13) 0.73394(10) 0.24528(12) 0.0269(3) Uani 1 1 d . . . . .
C6 C 0.09161(11) 0.52494(8) 0.25681(9) 0.0162(2) Uani 1 1 d . . . . .
C7 C 0.08540(11) 0.52831(9) 0.15778(10) 0.0188(2) Uani 1 1 d . . . . .
H7 H 0.0159 0.5318 0.1176 0.023 Uiso 1 1 calc R . . . .
C8 C 0.20602(11) 0.52536(8) 0.13214(9) 0.0163(2) Uani 1 1 d . . . . .
C9 C -0.00807(12) 0.52620(9) 0.32709(11) 0.0210(2) Uani 1 1 d . . . . .
C10 C 0.26038(13) 0.52643(9) 0.03558(9) 0.0202(2) Uani 1 1 d . . . . .
C11 C 0.32939(13) 0.45798(10) 0.53243(9) 0.0216(2) Uani 1 1 d . . . . .
C12 C 0.27062(12) 0.40133(9) 0.48570(9) 0.0189(2) Uani 1 1 d . . . . .
C13 C 0.21382(13) 0.31291(9) 0.45404(10) 0.0223(2) Uani 1 1 d . . . . .
H13A H 0.1270 0.3148 0.4695 0.027 Uiso 1 1 calc R . . . .
H13B H 0.2506 0.2611 0.4906 0.027 Uiso 1 1 calc R . . . .
C14 C 0.22641(12) 0.29269(9) 0.34721(10) 0.0199(2) Uani 1 1 d . . . . .
H14A H 0.1942 0.2298 0.3339 0.024 Uiso 1 1 calc R . . . .
H14B H 0.1763 0.3377 0.3109 0.024 Uiso 1 1 calc R . . . .
C15 C 0.35555(11) 0.29793(9) 0.31127(9) 0.0191(2) Uani 1 1 d . . . . .
H15A H 0.3929 0.3567 0.3334 0.023 Uiso 1 1 calc R . . . .
H15B H 0.4029 0.2459 0.3388 0.023 Uiso 1 1 calc R . . . .
C16 C 0.36088(12) 0.29334(9) 0.20276(10) 0.0203(2) Uani 1 1 d . . . . .
H16A H 0.3015 0.3378 0.1757 0.024 Uiso 1 1 calc R . . . .
H16B H 0.3366 0.2303 0.1819 0.024 Uiso 1 1 calc R . . . .
C17 C 0.48538(13) 0.31520(10) 0.16187(10) 0.0233(2) Uani 1 1 d . . . . .
H17A H 0.5419 0.2653 0.1815 0.028 Uiso 1 1 calc R . . . .
H17B H 0.4790 0.3140 0.0914 0.028 Uiso 1 1 calc R . . . .
C18 C 0.53759(11) 0.40577(9) 0.19140(9) 0.0190(2) Uani 1 1 d . . . . .
C19 C 0.61169(11) 0.46482(10) 0.21632(10) 0.0206(2) Uani 1 1 d . . . . .
H19 H 0.687(2) 0.4926(15) 0.2309(17) 0.036(6) Uiso 1 1 d . . . . .
H11 H 0.379(3) 0.4846(17) 0.579(2) 0.053(7) 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 1.9858(10) . ?
Cu1 N3 1.9630(10) . ?
Cu1 C11 1.9527(13) . ?
Cu1 C12 2.0053(12) . ?
Cu2 N2 1.9967(10) . ?
Cu2 N4 1.9658(10) . ?
Cu2 C18 2.0108(13) . ?
Cu2 C19 1.9574(13) . ?
F1 C4 1.3413(16) . ?
F2 C4 1.3409(16) . ?
F3 C4 1.3322(17) . ?
F4 C5 1.3293(18) . ?
F5 C5 1.3352(18) . ?
F6 C5 1.329(2) . ?
F7 C9 1.3398(17) . ?
F8 C9 1.3311(16) . ?
F9 C9 1.3276(16) . ?
F10 C10 1.3371(17) . ?
F11 C10 1.3308(15) . ?
F12 C10 1.3402(15) . ?
N1 N2 1.3572(14) . ?
N1 C1 1.3449(15) . ?
N2 C3 1.3436(15) . ?
N3 N4 1.3528(14) . ?
N3 C6 1.3422(15) . ?
N4 C8 1.3443(15) . ?
C1 C2 1.3833(18) . ?
C1 C4 1.4843(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.3831(19) . ?
C3 C5 1.4864(19) . ?
C6 C7 1.3903(18) . ?
C6 C9 1.4901(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.3897(18) . ?
C8 C10 1.4894(19) . ?
C11 C12 1.2279(19) . ?
C11 H11 0.93(3) . ?
C12 C13 1.4853(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.534(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5256(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5249(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.534(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.4832(19) . ?
C18 C19 1.2296(19) . ?
C19 H19 0.95(2) . ?

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 C12 145.25(5) . . ?
N3 Cu1 N1 97.92(4) . . ?
N3 Cu1 C12 114.39(5) . . ?
C11 Cu1 N1 111.08(5) . . ?
C11 Cu1 N3 150.47(5) . . ?
C11 Cu1 C12 36.12(6) . . ?
N2 Cu2 C18 145.07(5) . . ?
N4 Cu2 N2 98.34(4) . . ?
N4 Cu2 C18 113.99(5) . . ?
C19 Cu2 N2 111.77(5) . . ?
C19 Cu2 N4 149.70(5) . . ?
C19 Cu2 C18 36.07(6) . . ?
N2 N1 Cu1 116.64(7) . . ?
C1 N1 Cu1 135.79(9) . . ?
C1 N1 N2 107.48(10) . . ?
N1 N2 Cu2 116.41(7) . . ?
C3 N2 Cu2 136.17(9) . . ?
C3 N2 N1 107.40(10) . . ?
N4 N3 Cu1 116.56(7) . . ?
C6 N3 Cu1 135.66(9) . . ?
C6 N3 N4 107.71(10) . . ?
N3 N4 Cu2 117.43(7) . . ?
C8 N4 Cu2 134.60(9) . . ?
C8 N4 N3 107.84(10) . . ?
N1 C1 C2 111.06(11) . . ?
N1 C1 C4 120.09(11) . . ?
C2 C1 C4 128.81(12) . . ?
C1 C2 H2 128.6 . . ?
C3 C2 C1 102.86(11) . . ?
C3 C2 H2 128.6 . . ?
N2 C3 C2 111.19(11) . . ?
N2 C3 C5 120.17(12) . . ?
C2 C3 C5 128.64(12) . . ?
F1 C4 C1 110.89(12) . . ?
F2 C4 F1 106.33(11) . . ?
F2 C4 C1 112.89(11) . . ?
F3 C4 F1 107.63(12) . . ?
F3 C4 F2 106.63(12) . . ?
F3 C4 C1 112.12(11) . . ?
F4 C5 F5 106.51(13) . . ?
F4 C5 C3 111.26(13) . . ?
F5 C5 C3 112.64(12) . . ?
F6 C5 F4 107.56(14) . . ?
F6 C5 F5 106.56(15) . . ?
F6 C5 C3 111.97(12) . . ?
N3 C6 C7 110.89(11) . . ?
N3 C6 C9 119.87(11) . . ?
C7 C6 C9 129.24(11) . . ?
C6 C7 H7 128.6 . . ?
C8 C7 C6 102.83(11) . . ?
C8 C7 H7 128.6 . . ?
N4 C8 C7 110.73(11) . . ?
N4 C8 C10 119.71(11) . . ?
C7 C8 C10 129.56(11) . . ?
F7 C9 C6 111.97(11) . . ?
F8 C9 F7 105.66(13) . . ?
F8 C9 C6 113.03(11) . . ?
F9 C9 F7 107.55(12) . . ?
F9 C9 F8 107.30(11) . . ?
F9 C9 C6 110.98(12) . . ?
F10 C10 F12 107.41(12) . . ?
F10 C10 C8 112.08(11) . . ?
F11 C10 F10 106.04(12) . . ?
F11 C10 F12 106.97(11) . . ?
F11 C10 C8 113.12(11) . . ?
F12 C10 C8 110.87(12) . . ?
Cu1 C11 H11 123.0(16) . . ?
C12 C11 Cu1 74.28(8) . . ?
C12 C11 H11 162.2(16) . . ?
C11 C12 Cu1 69.61(8) . . ?
C11 C12 C13 161.54(13) . . ?
C13 C12 Cu1 128.44(9) . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C12 C13 C14 114.26(11) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C13 114.26(11) . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C14 112.10(11) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C15 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C15 C16 C17 114.26(11) . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C16 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C18 C17 C16 115.19(11) . . ?
C18 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
C17 C18 Cu2 129.36(9) . . ?
C19 C18 Cu2 69.60(8) . . ?
C19 C18 C17 160.71(13) . . ?
Cu2 C19 H19 125.9(14) . . ?
C18 C19 Cu2 74.33(8) . . ?
C18 C19 H19 159.7(14) . . ?

_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_rad230_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1934983'
loop_
_audit_author_name
_audit_author_address
'Rasika Dias'
;The University of Texas at Arlington
United States of America
;
_audit_update_record             
;
2019-06-18 deposited with the CCDC.	2019-09-05 downloaded from the CCDC.
;
_audit_creation_date             2019-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H14 Cu2 F12 N4'
_chemical_formula_sum            'C26 H14 Cu2 F12 N4'
_chemical_formula_weight         737.49
_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                   12.9771(15)
_cell_length_b                   13.6360(15)
_cell_length_c                   17.588(3)
_cell_angle_alpha                71.399(3)
_cell_angle_beta                 71.758(2)
_cell_angle_gamma                79.715(2)
_cell_volume                     2790.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    175(2)
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.737
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  0.4330
_exptl_absorpt_correction_T_min  0.3849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0496 before and 0.0405 after correction. The Ratio of minimum to maximum transmission is 0.8889. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35889
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.129
_diffrn_reflns_theta_min         2.950
_diffrn_ambient_temperature      175.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  
'Bruker D8 Quest with a Photon 100 CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11883
_reflns_number_total             14970
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.597
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     849
_refine_ls_number_reflns         14970
_refine_ls_number_restraints     117
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.119
_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)+(0.0771P)²+2.7681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1401
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F24A-C36 \\sim F22-C36 \\sim F22A-C36 \\sim F23-C36 \\sim F23A-C36 \\sim
F24-C36
 with sigma of 0.02
 F13-C30 \\sim F13A-C30 \\sim F14A-C30 \\sim F14-C30 \\sim F15-C30 \\sim
F15A-C30
 with sigma of 0.02
 F13-F14 \\sim F13-F15 \\sim F14-F15 \\sim F13A-F14A \\sim F13A-F15A \\sim
F14A-F15A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F24A) \\sim Ueq, Uanis(F22) \\sim Ueq, Uanis(F22A) \\sim Ueq, Uanis(F23)
\\sim Ueq, Uanis(F23A) \\sim Ueq, Uanis(F24) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.005
Uanis(F15A) \\sim Ueq, Uanis(F13) \\sim Ueq, Uanis(F13A) \\sim Ueq, Uanis(F14A)
\\sim Ueq, Uanis(F14) \\sim Ueq, Uanis(F15) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.005
4. Others
 Sof(F22A)=Sof(F23A)=Sof(F24A)=1-FVAR(1)
 Sof(F22)=Sof(F23)=Sof(F24)=FVAR(1)
 Sof(F13A)=Sof(F14A)=Sof(F15A)=1-FVAR(2)
 Sof(F13)=Sof(F14)=Sof(F15)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C33(H33),
  C37(H37), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45),
 C48(H48), C49(H49), C50(H50), C51(H51), C52(H52)
;
_atom_sites_solution_hydrogens   geom
_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 0.53856(2) -0.17691(2) 0.21531(2) 0.02530(8) Uani 1 1 d . . . . .
Cu2 Cu 0.70444(3) -0.03510(2) 0.06616(2) 0.02718(8) Uani 1 1 d . . . . .
F1 F 0.6520(4) -0.4335(3) 0.31025(18) 0.1273(16) Uani 1 1 d . . . . .
F2 F 0.5577(2) -0.4339(2) 0.2366(2) 0.0964(11) Uani 1 1 d . . . . .
F3 F 0.7055(2) -0.52557(17) 0.2245(2) 0.0873(10) Uani 1 1 d . . . . .
F4 F 0.94459(17) -0.11470(16) -0.00367(15) 0.0589(6) Uani 1 1 d . . . . .
F5 F 0.8966(2) -0.1849(2) -0.07853(13) 0.0666(6) Uani 1 1 d . . . . .
F6 F 1.00954(16) -0.27021(17) -0.01010(16) 0.0625(6) Uani 1 1 d . . . . .
F7 F 0.5780(3) -0.21133(18) 0.41094(17) 0.0867(10) Uani 1 1 d . . . . .
F8 F 0.43160(19) -0.1218(2) 0.39597(13) 0.0695(7) Uani 1 1 d . . . . .
F9 F 0.5281(2) -0.0757(2) 0.45334(12) 0.0624(6) Uani 1 1 d . . . . .
F10 F 0.7428(2) 0.22574(19) 0.1487(3) 0.1240(16) Uani 1 1 d . . . . .
F11 F 0.8174(2) 0.1236(2) 0.07444(14) 0.0750(8) Uani 1 1 d . . . . .
F12 F 0.8689(2) 0.1149(2) 0.17852(16) 0.0743(8) Uani 1 1 d . . . . .
N1 N 0.67514(18) -0.24915(17) 0.16250(14) 0.0291(4) Uani 1 1 d . . . . .
N2 N 0.74570(18) -0.18697(18) 0.09882(14) 0.0293(4) Uani 1 1 d . . . . .
N3 N 0.59874(17) -0.07181(17) 0.23965(13) 0.0268(4) Uani 1 1 d . . . . .
N4 N 0.66429(18) -0.00677(17) 0.17515(14) 0.0277(4) Uani 1 1 d . . . . .
C1 C 0.7171(2) -0.3476(2) 0.16912(18) 0.0337(6) Uani 1 1 d . . . . .
C2 C 0.8165(2) -0.3520(2) 0.10978(19) 0.0369(6) Uani 1 1 d . . . . .
H2 H 0.863756 -0.411397 0.100699 0.044 Uiso 1 1 calc R . . . .
C3 C 0.8298(2) -0.2491(2) 0.06733(18) 0.0332(6) Uani 1 1 d . . . . .
C4 C 0.6607(3) -0.4353(3) 0.2351(2) 0.0490(8) Uani 1 1 d . . . . .
C5 C 0.9210(3) -0.2049(3) -0.0057(2) 0.0436(7) Uani 1 1 d . . . . .
C6 C 0.5953(2) -0.0508(2) 0.30992(17) 0.0287(5) Uani 1 1 d . . . . .
C7 C 0.6586(2) 0.0292(2) 0.29250(18) 0.0331(6) Uani 1 1 d . . . . .
H7 H 0.670696 0.059771 0.330187 0.040 Uiso 1 1 calc R . . . .
C8 C 0.6998(2) 0.0539(2) 0.20672(17) 0.0297(5) Uani 1 1 d . . . . .
C9 C 0.5333(3) -0.1149(2) 0.39246(18) 0.0365(6) Uani 1 1 d . . . . .
C10 C 0.7797(3) 0.1314(3) 0.1524(2) 0.0409(7) Uani 1 1 d . . . . .
C11 C 0.4106(2) -0.2301(2) 0.21293(18) 0.0334(6) Uani 1 1 d . . . . .
H11 H 0.386969 -0.285599 0.202734 0.040 Uiso 1 1 calc R . . . .
C12 C 0.3785(2) -0.1489(2) 0.23252(16) 0.0293(5) Uani 1 1 d . . . . .
C13 C 0.3083(2) -0.0590(2) 0.25007(17) 0.0299(5) Uani 1 1 d . . . . .
C14 C 0.2005(3) -0.0712(3) 0.2979(2) 0.0456(7) Uani 1 1 d . . . . .
H14 H 0.175576 -0.138543 0.323449 0.055 Uiso 1 1 calc R . . . .
C15 C 0.1301(3) 0.0165(4) 0.3077(3) 0.0659(12) Uani 1 1 d . . . . .
H15 H 0.056731 0.008501 0.340308 0.079 Uiso 1 1 calc R . . . .
C16 C 0.1649(3) 0.1141(3) 0.2709(3) 0.0600(10) Uani 1 1 d . . . . .
H16 H 0.115643 0.173245 0.277665 0.072 Uiso 1 1 calc R . . . .
C17 C 0.2715(3) 0.1266(3) 0.2242(3) 0.0505(8) Uani 1 1 d . . . . .
H17 H 0.295610 0.194298 0.198460 0.061 Uiso 1 1 calc R . . . .
C18 C 0.3437(3) 0.0401(2) 0.2149(2) 0.0382(6) Uani 1 1 d . . . . .
H18 H 0.417688 0.048679 0.184222 0.046 Uiso 1 1 calc R . . . .
C19 C 0.7183(3) 0.0115(2) -0.05293(19) 0.0398(6) Uani 1 1 d . . . . .
H19 H 0.746946 -0.009839 -0.102458 0.048 Uiso 1 1 calc R . . . .
C20 C 0.6684(2) 0.0846(2) -0.02671(17) 0.0346(6) Uani 1 1 d . . . . .
C21 C 0.6050(2) 0.1821(2) -0.02139(17) 0.0342(6) Uani 1 1 d . . . . .
C22 C 0.4916(3) 0.1865(3) -0.0017(2) 0.0434(7) Uani 1 1 d . . . . .
H22 H 0.456807 0.124588 0.013678 0.052 Uiso 1 1 calc R . . . .
C23 C 0.4298(3) 0.2808(3) -0.0047(2) 0.0550(9) Uani 1 1 d . . . . .
H23 H 0.352738 0.283785 0.008448 0.066 Uiso 1 1 calc R . . . .
C24 C 0.4804(4) 0.3706(3) -0.0267(3) 0.0624(11) Uani 1 1 d . . . . .
H24 H 0.438059 0.435464 -0.029479 0.075 Uiso 1 1 calc R . . . .
C25 C 0.5918(4) 0.3666(3) -0.0447(3) 0.0552(9) Uani 1 1 d . . . . .
H25 H 0.625738 0.428852 -0.059360 0.066 Uiso 1 1 calc R . . . .
C26 C 0.6554(3) 0.2728(2) -0.0417(2) 0.0431(7) Uani 1 1 d . . . . .
H26 H 0.732259 0.270385 -0.053333 0.052 Uiso 1 1 calc R . . . .
Cu3 Cu 0.03083(3) 0.29668(2) 0.43937(2) 0.02659(8) Uani 1 1 d . . . . .
Cu4 Cu 0.18410(2) 0.44617(2) 0.28500(2) 0.02527(8) Uani 1 1 d . . . . .
F13 F -0.1374(8) 0.1451(5) 0.3390(5) 0.053(2) Uani 0.323(10) 1 d D U P A 1
F14 F -0.2576(7) 0.2688(9) 0.3524(9) 0.092(4) Uani 0.323(10) 1 d D U P A 1
F15 F -0.1664(10) 0.2105(9) 0.4399(6) 0.053(3) Uani 0.323(10) 1 d D U P A 1
F16 F 0.1152(3) 0.55263(19) 0.10555(14) 0.0749(8) Uani 1 1 d . . . . .
F17 F 0.2056(2) 0.4113(2) 0.09649(16) 0.0860(10) Uani 1 1 d . . . . .
F18 F 0.0631(2) 0.4574(2) 0.05384(13) 0.0763(8) Uani 1 1 d . . . . .
F19 F 0.27132(18) -0.00618(16) 0.51422(15) 0.0612(6) Uani 1 1 d . . . . .
F20 F 0.10790(18) 0.05681(18) 0.50679(15) 0.0610(6) Uani 1 1 d . . . . .
F21 F 0.1837(2) 0.10439(19) 0.57912(13) 0.0649(6) Uani 1 1 d . . . . .
F22 F 0.4276(5) 0.4011(5) 0.2096(4) 0.083(2) Uani 0.567(8) 1 d D U P B 1
F23 F 0.4920(4) 0.2471(4) 0.2040(3) 0.0705(16) Uani 0.567(8) 1 d D U P B 1
F24 F 0.5345(4) 0.3116(6) 0.2787(4) 0.087(2) Uani 0.567(8) 1 d D U P B 1
N5 N -0.00669(18) 0.33948(17) 0.33257(14) 0.0287(4) Uani 1 1 d . . . . .
N6 N 0.06438(18) 0.39650(17) 0.26587(13) 0.0269(4) Uani 1 1 d . . . . .
N7 N 0.18721(18) 0.24843(17) 0.40366(14) 0.0286(4) Uani 1 1 d . . . . .
N8 N 0.25360(18) 0.31133(17) 0.33658(14) 0.0292(4) Uani 1 1 d . . . . .
C27 C -0.0768(2) 0.3101(2) 0.30356(19) 0.0332(6) Uani 1 1 d . . . . .
C28 C -0.0527(2) 0.3467(2) 0.21785(19) 0.0355(6) Uani 1 1 d . . . . .
H28 H -0.089184 0.337343 0.181835 0.043 Uiso 1 1 calc R . . . .
C29 C 0.0377(2) 0.4006(2) 0.19715(17) 0.0294(5) Uani 1 1 d . . . . .
C30 C -0.1641(3) 0.2427(3) 0.3618(2) 0.0521(9) Uani 1 1 d D . . . .
C31 C 0.1054(3) 0.4546(3) 0.11355(19) 0.0385(6) Uani 1 1 d . . . . .
C32 C 0.2500(2) 0.1638(2) 0.43322(18) 0.0321(5) Uani 1 1 d . . . . .
C33 C 0.3572(2) 0.1700(2) 0.3867(2) 0.0370(6) Uani 1 1 d . . . . .
H33 H 0.417988 0.121310 0.394141 0.044 Uiso 1 1 calc R . . . .
C34 C 0.3549(2) 0.2642(2) 0.32649(18) 0.0340(6) Uani 1 1 d . . . . .
C35 C 0.2029(3) 0.0794(3) 0.5075(2) 0.0433(7) Uani 1 1 d . . . . .
C36 C 0.4474(3) 0.3117(3) 0.2565(2) 0.0532(9) Uani 1 1 d D . . . .
C37 C -0.0109(2) 0.2841(3) 0.55826(18) 0.0375(6) Uani 1 1 d . . . . .
H37 H 0.013401 0.254702 0.607083 0.045 Uiso 1 1 calc R . . . .
C38 C -0.0867(2) 0.3363(2) 0.53312(17) 0.0324(5) Uani 1 1 d . . . . .
C39 C -0.1868(2) 0.4023(2) 0.52874(17) 0.0332(6) Uani 1 1 d . . . . .
C40 C -0.1848(3) 0.5094(3) 0.5027(2) 0.0436(7) Uani 1 1 d . . . . .
H40 H -0.117241 0.539441 0.482327 0.052 Uiso 1 1 calc R . . . .
C41 C -0.2812(4) 0.5725(3) 0.5063(3) 0.0570(9) Uani 1 1 d . . . . .
H41 H -0.279624 0.645863 0.489011 0.068 Uiso 1 1 calc R . . . .
C42 C -0.3802(3) 0.5296(4) 0.5349(3) 0.0591(10) Uani 1 1 d . . . . .
H42 H -0.446313 0.573158 0.537938 0.071 Uiso 1 1 calc R . . . .
C43 C -0.3819(3) 0.4225(3) 0.5591(2) 0.0514(9) Uani 1 1 d . . . . .
H43 H -0.449604 0.392967 0.578198 0.062 Uiso 1 1 calc R . . . .
C44 C -0.2864(2) 0.3585(3) 0.5558(2) 0.0405(7) Uani 1 1 d . . . . .
H44 H -0.288125 0.285262 0.571698 0.049 Uiso 1 1 calc R . . . .
C45 C 0.2545(2) 0.5611(2) 0.28322(19) 0.0349(6) Uani 1 1 d . . . . .
H45 H 0.317563 0.578316 0.291030 0.042 Uiso 1 1 calc R . . . .
C46 C 0.1683(2) 0.5983(2) 0.26586(16) 0.0300(5) Uani 1 1 d . . . . .
C47 C 0.0772(2) 0.6731(2) 0.25003(17) 0.0303(5) Uani 1 1 d . . . . .
C48 C -0.0290(3) 0.6438(3) 0.2797(2) 0.0390(6) Uani 1 1 d . . . . .
H48 H -0.042209 0.572852 0.305801 0.047 Uiso 1 1 calc R . . . .
C49 C -0.1151(3) 0.7188(3) 0.2707(3) 0.0505(8) Uani 1 1 d . . . . .
H49 H -0.187767 0.699527 0.292206 0.061 Uiso 1 1 calc R . . . .
C50 C -0.0957(4) 0.8213(3) 0.2307(3) 0.0592(10) Uani 1 1 d . . . . .
H50 H -0.154898 0.872345 0.223834 0.071 Uiso 1 1 calc R . . . .
C51 C 0.0093(4) 0.8501(3) 0.2006(3) 0.0610(10) Uani 1 1 d . . . . .
H51 H 0.022164 0.920884 0.173193 0.073 Uiso 1 1 calc R . . . .
C52 C 0.0959(3) 0.7765(2) 0.2100(2) 0.0435(7) Uani 1 1 d . . . . .
H52 H 0.168239 0.796584 0.189171 0.052 Uiso 1 1 calc R . . . .
F22A F 0.4126(6) 0.3631(6) 0.1882(4) 0.067(2) Uani 0.433(8) 1 d D U P B 2
F23A F 0.5305(6) 0.2515(6) 0.2498(6) 0.092(3) Uani 0.433(8) 1 d D U P B 2
F24A F 0.4765(7) 0.3882(7) 0.2769(5) 0.093(3) Uani 0.433(8) 1 d D U P B 2
F13A F -0.1982(6) 0.1907(6) 0.3286(3) 0.093(2) Uani 0.677(10) 1 d D U P A 2
F14A F -0.2572(3) 0.3047(4) 0.3912(3) 0.0763(16) Uani 0.677(10) 1 d D U P A 2
F15A F -0.1385(5) 0.1860(5) 0.4321(3) 0.0633(16) Uani 0.677(10) 1 d D U P A 2


_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 1.976(2) . ?
Cu1 N3 1.962(2) . ?
Cu1 C11 1.944(3) . ?
Cu1 C12 1.987(3) . ?
Cu2 N2 1.986(2) . ?
Cu2 N4 1.967(2) . ?
Cu2 C19 1.944(3) . ?
Cu2 C20 2.014(3) . ?
F1 C4 1.298(5) . ?
F2 C4 1.325(5) . ?
F3 C4 1.308(4) . ?
F4 C5 1.332(4) . ?
F5 C5 1.348(4) . ?
F6 C5 1.320(4) . ?
F7 C9 1.320(4) . ?
F8 C9 1.320(4) . ?
F9 C9 1.321(3) . ?
F10 C10 1.279(4) . ?
F11 C10 1.335(4) . ?
F12 C10 1.333(4) . ?
N1 N2 1.357(3) . ?
N1 C1 1.339(4) . ?
N2 C3 1.344(3) . ?
N3 N4 1.349(3) . ?
N3 C6 1.341(3) . ?
N4 C8 1.340(3) . ?
C1 C2 1.387(4) . ?
C1 C4 1.487(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(4) . ?
C3 C5 1.491(4) . ?
C6 C7 1.382(4) . ?
C6 C9 1.493(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(4) . ?
C8 C10 1.493(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.228(4) . ?
C12 C13 1.447(4) . ?
C13 C14 1.396(4) . ?
C13 C18 1.388(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.371(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.225(4) . ?
C20 C21 1.446(4) . ?
C21 C22 1.397(4) . ?
C21 C26 1.396(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.375(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.389(5) . ?
C26 H26 0.9500 . ?
Cu3 N5 1.969(2) . ?
Cu3 N7 1.984(2) . ?
Cu3 C37 1.947(3) . ?
Cu3 C38 2.009(3) . ?
Cu4 N6 1.958(2) . ?
Cu4 N8 1.968(2) . ?
Cu4 C45 1.938(3) . ?
Cu4 C46 1.975(3) . ?
F13 C30 1.464(7) . ?
F14 C30 1.248(8) . ?
F15 C30 1.294(9) . ?
F16 C31 1.323(4) . ?
F17 C31 1.313(4) . ?
F18 C31 1.316(4) . ?
F19 C35 1.331(4) . ?
F20 C35 1.328(4) . ?
F21 C35 1.345(4) . ?
F22 C36 1.270(6) . ?
F23 C36 1.403(6) . ?
F24 C36 1.306(6) . ?
N5 N6 1.352(3) . ?
N5 C27 1.342(3) . ?
N6 C29 1.340(3) . ?
N7 N8 1.361(3) . ?
N7 C32 1.346(3) . ?
N8 C34 1.340(4) . ?
C27 C28 1.378(4) . ?
C27 C30 1.491(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.386(4) . ?
C29 C31 1.486(4) . ?
C30 F13A 1.256(5) . ?
C30 F14A 1.401(6) . ?
C30 F15A 1.340(6) . ?
C32 C33 1.378(4) . ?
C32 C35 1.482(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.382(4) . ?
C34 C36 1.489(4) . ?
C36 F22A 1.352(7) . ?
C36 F23A 1.232(6) . ?
C36 F24A 1.351(7) . ?
C37 H37 0.9500 . ?
C37 C38 1.221(4) . ?
C38 C39 1.450(4) . ?
C39 C40 1.388(4) . ?
C39 C44 1.401(4) . ?
C40 H40 0.9500 . ?
C40 C41 1.382(5) . ?
C41 H41 0.9500 . ?
C41 C42 1.386(6) . ?
C42 H42 0.9500 . ?
C42 C43 1.386(6) . ?
C43 H43 0.9500 . ?
C43 C44 1.380(5) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C45 C46 1.231(4) . ?
C46 C47 1.453(4) . ?
C47 C48 1.395(4) . ?
C47 C52 1.386(4) . ?
C48 H48 0.9500 . ?
C48 C49 1.385(4) . ?
C49 H49 0.9500 . ?
C49 C50 1.379(6) . ?
C50 H50 0.9500 . ?
C50 C51 1.377(6) . ?
C51 H51 0.9500 . ?
C51 C52 1.381(5) . ?
C52 H52 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 C12 146.91(10) . . ?
N3 Cu1 N1 99.77(9) . . ?
N3 Cu1 C12 111.63(10) . . ?
C11 Cu1 N1 112.02(11) . . ?
C11 Cu1 N3 147.93(11) . . ?
C11 Cu1 C12 36.38(12) . . ?
N2 Cu2 C20 143.63(11) . . ?
N4 Cu2 N2 100.57(9) . . ?
N4 Cu2 C20 114.73(11) . . ?
C19 Cu2 N2 108.86(11) . . ?
C19 Cu2 N4 150.52(11) . . ?
C19 Cu2 C20 36.01(13) . . ?
N2 N1 Cu1 115.36(17) . . ?
C1 N1 Cu1 136.77(19) . . ?
C1 N1 N2 107.7(2) . . ?
N1 N2 Cu2 118.71(17) . . ?
C3 N2 Cu2 133.89(19) . . ?
C3 N2 N1 107.2(2) . . ?
N4 N3 Cu1 117.70(16) . . ?
C6 N3 Cu1 134.17(19) . . ?
C6 N3 N4 108.0(2) . . ?
N3 N4 Cu2 116.90(16) . . ?
C8 N4 Cu2 134.84(19) . . ?
C8 N4 N3 107.3(2) . . ?
N1 C1 C2 110.8(2) . . ?
N1 C1 C4 121.2(3) . . ?
C2 C1 C4 128.0(3) . . ?
C1 C2 H2 128.5 . . ?
C3 C2 C1 103.0(3) . . ?
C3 C2 H2 128.5 . . ?
N2 C3 C2 111.3(2) . . ?
N2 C3 C5 120.8(3) . . ?
C2 C3 C5 127.9(3) . . ?
F1 C4 F2 102.3(4) . . ?
F1 C4 F3 110.3(4) . . ?
F1 C4 C1 113.4(3) . . ?
F2 C4 C1 113.2(3) . . ?
F3 C4 F2 104.6(3) . . ?
F3 C4 C1 112.2(3) . . ?
F4 C5 F5 105.8(3) . . ?
F4 C5 C3 112.0(3) . . ?
F5 C5 C3 112.0(3) . . ?
F6 C5 F4 109.2(3) . . ?
F6 C5 F5 106.2(3) . . ?
F6 C5 C3 111.4(3) . . ?
N3 C6 C7 110.7(2) . . ?
N3 C6 C9 120.1(2) . . ?
C7 C6 C9 129.2(3) . . ?
C6 C7 H7 128.6 . . ?
C6 C7 C8 102.9(2) . . ?
C8 C7 H7 128.6 . . ?
N4 C8 C7 111.1(2) . . ?
N4 C8 C10 121.3(3) . . ?
C7 C8 C10 127.5(3) . . ?
F7 C9 F8 106.0(3) . . ?
F7 C9 F9 107.7(3) . . ?
F7 C9 C6 111.9(3) . . ?
F8 C9 F9 106.1(3) . . ?
F8 C9 C6 113.2(2) . . ?
F9 C9 C6 111.5(3) . . ?
F10 C10 F11 107.9(4) . . ?
F10 C10 F12 106.6(3) . . ?
F10 C10 C8 114.1(3) . . ?
F11 C10 C8 112.3(2) . . ?
F12 C10 F11 103.8(3) . . ?
F12 C10 C8 111.4(3) . . ?
Cu1 C11 H11 143.1 . . ?
C12 C11 Cu1 73.72(18) . . ?
C12 C11 H11 143.1 . . ?
C11 C12 Cu1 69.90(18) . . ?
C11 C12 C13 160.7(3) . . ?
C13 C12 Cu1 128.9(2) . . ?
C14 C13 C12 119.3(3) . . ?
C18 C13 C12 121.1(3) . . ?
C18 C13 C14 119.4(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(4) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 119.9(4) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.4(3) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
Cu2 C19 H19 142.4 . . ?
C20 C19 Cu2 75.1(2) . . ?
C20 C19 H19 142.4 . . ?
C19 C20 Cu2 68.87(19) . . ?
C19 C20 C21 162.2(3) . . ?
C21 C20 Cu2 128.5(2) . . ?
C22 C21 C20 119.0(3) . . ?
C26 C21 C20 121.1(3) . . ?
C26 C21 C22 119.7(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.9(4) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.3(4) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.8(4) . . ?
C26 C25 H25 119.6 . . ?
C21 C26 H26 120.4 . . ?
C25 C26 C21 119.2(3) . . ?
C25 C26 H26 120.4 . . ?
N5 Cu3 N7 100.98(9) . . ?
N5 Cu3 C38 114.12(11) . . ?
N7 Cu3 C38 143.86(11) . . ?
C37 Cu3 N5 149.81(11) . . ?
C37 Cu3 N7 109.16(11) . . ?
C37 Cu3 C38 35.91(12) . . ?
N6 Cu4 N8 98.88(9) . . ?
N6 Cu4 C46 112.62(10) . . ?
N8 Cu4 C46 146.94(10) . . ?
C45 Cu4 N6 149.19(11) . . ?
C45 Cu4 N8 111.71(11) . . ?
C45 Cu4 C46 36.66(12) . . ?
N6 N5 Cu3 116.53(16) . . ?
C27 N5 Cu3 134.93(19) . . ?
C27 N5 N6 107.1(2) . . ?
N5 N6 Cu4 118.13(16) . . ?
C29 N6 Cu4 133.68(19) . . ?
C29 N6 N5 108.0(2) . . ?
N8 N7 Cu3 118.59(17) . . ?
C32 N7 Cu3 134.27(19) . . ?
C32 N7 N8 107.1(2) . . ?
N7 N8 Cu4 115.74(17) . . ?
C34 N8 Cu4 136.45(19) . . ?
C34 N8 N7 107.7(2) . . ?
N5 C27 C28 111.3(3) . . ?
N5 C27 C30 120.5(3) . . ?
C28 C27 C30 128.1(3) . . ?
C27 C28 H28 128.5 . . ?
C27 C28 C29 102.9(2) . . ?
C29 C28 H28 128.5 . . ?
N6 C29 C28 110.6(2) . . ?
N6 C29 C31 120.0(2) . . ?
C28 C29 C31 129.4(3) . . ?
F13 C30 C27 105.1(4) . . ?
F14 C30 F13 101.4(6) . . ?
F14 C30 F15 111.6(8) . . ?
F14 C30 C27 116.8(6) . . ?
F15 C30 F13 101.3(6) . . ?
F15 C30 C27 117.6(6) . . ?
F13A C30 C27 114.5(4) . . ?
F13A C30 F14A 103.4(4) . . ?
F13A C30 F15A 113.4(5) . . ?
F14A C30 C27 109.6(3) . . ?
F15A C30 C27 112.2(4) . . ?
F15A C30 F14A 102.4(4) . . ?
F16 C31 C29 113.1(3) . . ?
F17 C31 F16 105.2(3) . . ?
F17 C31 F18 108.1(3) . . ?
F17 C31 C29 112.7(3) . . ?
F18 C31 F16 105.6(3) . . ?
F18 C31 C29 111.7(3) . . ?
N7 C32 C33 111.1(2) . . ?
N7 C32 C35 121.1(3) . . ?
C33 C32 C35 127.7(3) . . ?
C32 C33 H33 128.4 . . ?
C32 C33 C34 103.2(2) . . ?
C34 C33 H33 128.4 . . ?
N8 C34 C33 110.9(2) . . ?
N8 C34 C36 121.3(3) . . ?
C33 C34 C36 127.8(3) . . ?
F19 C35 F21 105.5(3) . . ?
F19 C35 C32 111.1(3) . . ?
F20 C35 F19 109.3(3) . . ?
F20 C35 F21 105.8(3) . . ?
F20 C35 C32 112.5(3) . . ?
F21 C35 C32 112.3(3) . . ?
F22 C36 F23 106.2(5) . . ?
F22 C36 F24 108.9(6) . . ?
F22 C36 C34 117.3(3) . . ?
F23 C36 C34 110.3(3) . . ?
F24 C36 F23 97.7(5) . . ?
F24 C36 C34 114.3(4) . . ?
F22A C36 C34 110.0(4) . . ?
F23A C36 C34 112.3(4) . . ?
F23A C36 F22A 119.5(7) . . ?
F23A C36 F24A 102.9(7) . . ?
F24A C36 C34 107.6(4) . . ?
F24A C36 F22A 103.2(6) . . ?
Cu3 C37 H37 142.6 . . ?
C38 C37 Cu3 74.82(19) . . ?
C38 C37 H37 142.6 . . ?
C37 C38 Cu3 69.27(19) . . ?
C37 C38 C39 162.4(3) . . ?
C39 C38 Cu3 128.0(2) . . ?
C40 C39 C38 119.8(3) . . ?
C40 C39 C44 119.8(3) . . ?
C44 C39 C38 120.3(3) . . ?
C39 C40 H40 120.0 . . ?
C41 C40 C39 120.0(3) . . ?
C41 C40 H40 120.0 . . ?
C40 C41 H41 119.8 . . ?
C40 C41 C42 120.5(4) . . ?
C42 C41 H41 119.8 . . ?
C41 C42 H42 120.2 . . ?
C43 C42 C41 119.5(3) . . ?
C43 C42 H42 120.2 . . ?
C42 C43 H43 119.7 . . ?
C44 C43 C42 120.7(3) . . ?
C44 C43 H43 119.7 . . ?
C39 C44 H44 120.2 . . ?
C43 C44 C39 119.6(3) . . ?
C43 C44 H44 120.2 . . ?
Cu4 C45 H45 143.3 . . ?
C46 C45 Cu4 73.35(18) . . ?
C46 C45 H45 143.3 . . ?
C45 C46 Cu4 69.99(18) . . ?
C45 C46 C47 160.0(3) . . ?
C47 C46 Cu4 129.5(2) . . ?
C48 C47 C46 120.9(3) . . ?
C52 C47 C46 119.1(3) . . ?
C52 C47 C48 119.9(3) . . ?
C47 C48 H48 120.2 . . ?
C49 C48 C47 119.5(3) . . ?
C49 C48 H48 120.2 . . ?
C48 C49 H49 119.9 . . ?
C50 C49 C48 120.2(4) . . ?
C50 C49 H49 119.9 . . ?
C49 C50 H50 119.9 . . ?
C51 C50 C49 120.2(3) . . ?
C51 C50 H50 119.9 . . ?
C50 C51 H51 119.8 . . ?
C50 C51 C52 120.3(3) . . ?
C52 C51 H51 119.8 . . ?
C47 C52 H52 120.1 . . ?
C51 C52 C47 119.9(3) . . ?
C51 C52 H52 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT910_rad230_0m_a         
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         16 Note  
RESPONSE: These refelections were partially obstructed by hardware
;
####################################################################### 
# 
# 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_rad517_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1934986'
loop_
_audit_author_name
_audit_author_address
'Rasika Dias'
;The University of Texas at Arlington
United States of America
;
_audit_update_record             
;
2019-06-18 deposited with the CCDC.	2019-09-05 downloaded from the CCDC.
;
_audit_creation_date             2017-06-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 Cu2 F12 N4'
_chemical_formula_sum            'C22 H20 Cu2 F12 N4'
_chemical_formula_weight         695.50
_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                   8.4602(3)
_cell_length_b                   9.2660(4)
_cell_length_c                   17.3777(7)
_cell_angle_alpha                97.7580(10)
_cell_angle_beta                 90.3530(10)
_cell_angle_gamma                107.1170(10)
_cell_volume                     1288.50(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.41
_cell_measurement_theta_min      3.03
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.678
_exptl_absorpt_coefficient_mu    1.757
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0499 before and 0.0366 after correction. The Ratio of minimum to maximum transmission is 0.8953. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plates
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17811
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.414
_diffrn_reflns_theta_min         2.755
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  
'Bruker D8 Quest with a Photon 100 CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6796
_reflns_number_total             7741
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         7741
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.041
_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)+(0.0308P)²+0.8429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0685
_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:
 C15(H15A,H15B), C18(H18A,H18B), C16(H16A,H16B), C17(H17A,H17B), C21(H21A,
 H21B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_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 0.35783(2) 0.70080(2) 0.76353(2) 0.01147(5) Uani 1 1 d . . . . .
Cu2 Cu 0.61981(2) 0.62642(2) 0.27280(2) 0.01143(5) Uani 1 1 d . . . . .
F8 F 0.73593(15) 0.87928(11) 0.16241(6) 0.0293(2) Uani 1 1 d . . . . .
F12 F 0.66445(14) 0.14009(11) 0.04844(7) 0.0306(2) Uani 1 1 d . . . . .
F2 F 0.08435(15) 0.81730(12) 0.70497(6) 0.0308(2) Uani 1 1 d . . . . .
F9 F 0.53253(14) 0.78022(13) 0.07907(7) 0.0323(2) Uani 1 1 d . . . . .
F7 F 0.78018(15) 0.84925(12) 0.03978(6) 0.0294(2) Uani 1 1 d . . . . .
F10 F 0.83334(16) 0.27045(13) -0.02503(6) 0.0335(3) Uani 1 1 d . . . . .
F6 F -0.12302(13) 0.10175(12) 0.57562(7) 0.0319(2) Uani 1 1 d . . . . .
F1 F 0.08475(18) 0.78392(13) 0.58120(7) 0.0381(3) Uani 1 1 d . . . . .
F11 F 0.91479(17) 0.25300(15) 0.08907(8) 0.0457(4) Uani 1 1 d . . . . .
F4 F 0.12941(15) 0.13161(14) 0.55308(9) 0.0487(4) Uani 1 1 d . . . . .
N3 N 0.66478(16) 0.56368(14) 0.16410(7) 0.0134(2) Uani 1 1 d . . . . .
N1 N 0.18767(15) 0.56315(13) 0.68664(7) 0.0120(2) Uani 1 1 d . . . . .
N2 N 0.19076(15) 0.41639(13) 0.67611(7) 0.0123(2) Uani 1 1 d . . . . .
N4 N 0.68796(16) 0.42404(13) 0.15056(7) 0.0133(2) Uani 1 1 d . . . . .
F3 F -0.14056(15) 0.69604(15) 0.63818(11) 0.0552(4) Uani 1 1 d . . . . .
F5 F 0.0452(3) 0.10124(14) 0.66730(8) 0.0662(6) Uani 1 1 d . . . . .
C19 C 0.47458(18) 0.66889(16) 0.35547(8) 0.0139(2) Uani 1 1 d . . . . .
C14 C 0.51243(18) 0.87183(16) 0.71922(8) 0.0150(3) Uani 1 1 d . . . . .
C8 C 0.74326(18) 0.40738(16) 0.07864(8) 0.0144(3) Uani 1 1 d . . . . .
C15 C 0.49886(19) 0.90333(16) 0.63851(8) 0.0146(3) Uani 1 1 d . . . . .
H15A H 0.5900 0.9949 0.6308 0.018 Uiso 1 1 calc R . . . .
H15B H 0.3929 0.9255 0.6303 0.018 Uiso 1 1 calc R . . . .
C18 C 0.49551(18) 0.65513(16) 0.43863(8) 0.0136(2) Uani 1 1 d . . . . .
H18A H 0.6037 0.6376 0.4474 0.016 Uiso 1 1 calc R . . . .
H18B H 0.4080 0.5647 0.4508 0.016 Uiso 1 1 calc R . . . .
C6 C 0.70621(18) 0.63110(16) 0.10025(8) 0.0144(3) Uani 1 1 d . . . . .
C3 C 0.06279(18) 0.33487(16) 0.62699(8) 0.0139(3) Uani 1 1 d . . . . .
C13 C 0.56319(19) 0.87299(17) 0.78600(9) 0.0172(3) Uani 1 1 d . . . . .
C1 C 0.05806(18) 0.56951(16) 0.64383(8) 0.0141(3) Uani 1 1 d . . . . .
C20 C 0.41315(18) 0.68336(17) 0.29343(8) 0.0150(3) Uani 1 1 d . . . . .
C16 C 0.50652(19) 0.76897(16) 0.57843(8) 0.0143(3) Uani 1 1 d . . . . .
H16A H 0.6139 0.7491 0.5860 0.017 Uiso 1 1 calc R . . . .
H16B H 0.4177 0.6768 0.5877 0.017 Uiso 1 1 calc R . . . .
C9 C 0.6895(2) 0.78479(18) 0.09570(9) 0.0193(3) Uani 1 1 d . . . . .
C7 C 0.75770(19) 0.53658(17) 0.04359(8) 0.0164(3) Uani 1 1 d . . . . .
H7 H 0.7939 0.5555 -0.0067 0.020 Uiso 1 1 calc R . . . .
C17 C 0.48758(18) 0.79529(16) 0.49469(8) 0.0126(2) Uani 1 1 d . . . . .
H17A H 0.5771 0.8860 0.4844 0.015 Uiso 1 1 calc R . . . .
H17B H 0.3802 0.8147 0.4863 0.015 Uiso 1 1 calc R . . . .
C10 C 0.7881(2) 0.26747(17) 0.04822(9) 0.0178(3) Uani 1 1 d . . . . .
C2 C -0.02632(18) 0.42707(17) 0.60428(9) 0.0164(3) Uani 1 1 d . . . . .
H2 H -0.1217 0.3994 0.5700 0.020 Uiso 1 1 calc R . . . .
C4 C 0.0209(2) 0.71626(18) 0.64240(10) 0.0209(3) Uani 1 1 d . . . . .
C21 C 0.2979(2) 0.7061(2) 0.23523(9) 0.0208(3) Uani 1 1 d . . . . .
H21A H 0.3610 0.7790 0.2017 0.025 Uiso 1 1 calc R . . . .
H21B H 0.2173 0.7513 0.2624 0.025 Uiso 1 1 calc R . . . .
C5 C 0.0298(2) 0.16761(18) 0.60614(10) 0.0204(3) Uani 1 1 d . . . . .
C12 C 0.6657(2) 0.9110(2) 0.85985(9) 0.0246(3) Uani 1 1 d . . . . .
H12A H 0.6448 0.8184 0.8855 0.029 Uiso 1 1 calc R . . . .
H12B H 0.6316 0.9885 0.8951 0.029 Uiso 1 1 calc R . . . .
C22 C 0.2043(2) 0.5575(2) 0.18462(11) 0.0326(4) Uani 1 1 d . . . . .
H22A H 0.1279 0.5775 0.1478 0.049 Uiso 1 1 calc GR . . . .
H22B H 0.1416 0.4848 0.2176 0.049 Uiso 1 1 calc GR . . . .
H22C H 0.2833 0.5145 0.1559 0.049 Uiso 1 1 calc GR . . . .
C11 C 0.8480(2) 0.9709(3) 0.84768(11) 0.0321(4) Uani 1 1 d . . . . .
H11A H 0.8830 0.8939 0.8136 0.048 Uiso 1 1 calc GR . . . .
H11B H 0.9099 0.9936 0.8979 0.048 Uiso 1 1 calc GR . . . .
H11C H 0.8700 1.0642 0.8236 0.048 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 1.9799(12) . ?
Cu1 N4 1.9816(12) 2_666 ?
Cu1 C14 1.9841(15) . ?
Cu1 C13 1.9770(15) . ?
Cu2 N3 1.9731(12) . ?
Cu2 N2 1.9915(12) 2_666 ?
Cu2 C19 1.9704(14) . ?
Cu2 C20 1.9908(14) . ?
F8 C9 1.3351(18) . ?
F12 C10 1.3274(19) . ?
F2 C4 1.330(2) . ?
F9 C9 1.344(2) . ?
F7 C9 1.3363(18) . ?
F10 C10 1.3330(18) . ?
F6 C5 1.3282(19) . ?
F1 C4 1.343(2) . ?
F11 C10 1.3310(19) . ?
F4 C5 1.328(2) . ?
N3 N4 1.3549(16) . ?
N3 C6 1.3445(18) . ?
N1 N2 1.3554(16) . ?
N1 C1 1.3413(18) . ?
N2 Cu2 1.9915(12) 2_666 ?
N2 C3 1.3433(18) . ?
N4 Cu1 1.9816(12) 2_666 ?
N4 C8 1.3425(18) . ?
F3 C4 1.323(2) . ?
F5 C5 1.322(2) . ?
C19 C18 1.4819(19) . ?
C19 C20 1.234(2) . ?
C14 C15 1.481(2) . ?
C14 C13 1.233(2) . ?
C8 C7 1.390(2) . ?
C8 C10 1.487(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5303(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C17 1.5332(19) . ?
C6 C9 1.484(2) . ?
C6 C7 1.387(2) . ?
C3 C2 1.386(2) . ?
C3 C5 1.484(2) . ?
C13 C12 1.486(2) . ?
C1 C2 1.385(2) . ?
C1 C4 1.486(2) . ?
C20 C21 1.478(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5227(19) . ?
C7 H7 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C2 H2 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.523(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.505(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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 N4 97.89(5) . 2_666 ?
N1 Cu1 C14 113.33(5) . . ?
N4 Cu1 C14 147.53(6) 2_666 . ?
C13 Cu1 N1 149.06(6) . . ?
C13 Cu1 N4 111.53(6) . 2_666 ?
C13 Cu1 C14 36.26(6) . . ?
N3 Cu2 N2 97.80(5) . 2_666 ?
N3 Cu2 C20 118.36(6) . . ?
C19 Cu2 N3 153.16(6) . . ?
C19 Cu2 N2 107.14(6) . 2_666 ?
C19 Cu2 C20 36.31(6) . . ?
C20 Cu2 N2 143.43(5) . 2_666 ?
N4 N3 Cu2 114.39(9) . . ?
C6 N3 Cu2 136.84(10) . . ?
C6 N3 N4 107.68(11) . . ?
N2 N1 Cu1 114.13(9) . . ?
C1 N1 Cu1 138.13(10) . . ?
C1 N1 N2 107.55(11) . . ?
N1 N2 Cu2 116.83(9) . 2_666 ?
C3 N2 Cu2 135.38(10) . 2_666 ?
C3 N2 N1 107.62(11) . . ?
N3 N4 Cu1 116.79(9) . 2_666 ?
C8 N4 Cu1 135.53(10) . 2_666 ?
C8 N4 N3 107.65(11) . . ?
C18 C19 Cu2 125.59(10) . . ?
C20 C19 Cu2 72.75(9) . . ?
C20 C19 C18 161.30(15) . . ?
C15 C14 Cu1 124.74(10) . . ?
C13 C14 Cu1 71.56(10) . . ?
C13 C14 C15 163.40(15) . . ?
N4 C8 C7 110.93(13) . . ?
N4 C8 C10 120.35(13) . . ?
C7 C8 C10 128.63(13) . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C14 C15 C16 112.06(12) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C19 C18 C17 113.97(11) . . ?
H18A C18 H18B 107.7 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
N3 C6 C9 120.94(13) . . ?
N3 C6 C7 110.90(13) . . ?
C7 C6 C9 128.13(13) . . ?
N2 C3 C2 110.89(13) . . ?
N2 C3 C5 120.34(13) . . ?
C2 C3 C5 128.73(14) . . ?
C14 C13 Cu1 72.18(10) . . ?
C14 C13 C12 163.06(16) . . ?
C12 C13 Cu1 124.68(12) . . ?
N1 C1 C2 111.07(12) . . ?
N1 C1 C4 120.87(13) . . ?
C2 C1 C4 128.06(13) . . ?
C19 C20 Cu2 70.94(9) . . ?
C19 C20 C21 162.03(15) . . ?
C21 C20 Cu2 126.90(11) . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.56(12) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
F8 C9 F9 106.04(13) . . ?
F8 C9 F7 107.97(14) . . ?
F8 C9 C6 112.52(13) . . ?
F9 C9 C6 112.37(13) . . ?
F7 C9 F9 106.47(13) . . ?
F7 C9 C6 111.12(13) . . ?
C8 C7 H7 128.6 . . ?
C6 C7 C8 102.83(13) . . ?
C6 C7 H7 128.6 . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C16 C17 C18 110.06(11) . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.2 . . ?
F12 C10 F10 106.66(13) . . ?
F12 C10 F11 106.83(14) . . ?
F12 C10 C8 113.18(13) . . ?
F10 C10 C8 110.95(13) . . ?
F11 C10 F10 106.69(14) . . ?
F11 C10 C8 112.14(13) . . ?
C3 C2 H2 128.6 . . ?
C1 C2 C3 102.86(13) . . ?
C1 C2 H2 128.6 . . ?
F2 C4 F1 105.75(14) . . ?
F2 C4 C1 112.45(13) . . ?
F1 C4 C1 111.95(14) . . ?
F3 C4 F2 107.74(15) . . ?
F3 C4 F1 107.18(15) . . ?
F3 C4 C1 111.43(14) . . ?
C20 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
C20 C21 C22 112.23(15) . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
F6 C5 F4 105.68(13) . . ?
F6 C5 C3 111.26(13) . . ?
F4 C5 C3 112.79(14) . . ?
F5 C5 F6 107.07(15) . . ?
F5 C5 F4 107.67(16) . . ?
F5 C5 C3 112.00(13) . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C13 C12 C11 112.71(15) . . ?
H12A C12 H12B 107.8 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#===END
