# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

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

data_cmpd_3
_database_code_depnum_ccdc_archive 'CCDC 1031118'
_audit_update_record             
;
2014-10-27 deposited with the CCDC.
2015-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            '[Me2NN]Cu(h2-ArFN=ArF)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H31 Cu F12 N4'
_chemical_formula_sum            'C37 H31 Cu F12 N4'
_chemical_formula_weight         823.20

_journal_name_requested          'Chem. Sci.'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   12.1667(16)
_cell_length_b                   12.1867(16)
_cell_length_c                   13.5954(18)
_cell_angle_alpha                81.549(2)
_cell_angle_beta                 77.873(2)
_cell_angle_gamma                65.444(2)
_cell_volume                     1788.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5845
_cell_measurement_theta_min      4.423
_cell_measurement_theta_max      53.393

_exptl_crystal_description       block
_exptl_crystal_colour            red-orange
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             836
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7850
_exptl_absorpt_correction_T_max  0.8118
_exptl_absorpt_process_details   
"SADABS based on Blessing's method; Blessing, Acta Cryst. (1995) A51 33-38"

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19867
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         27.00
_reflns_number_total             7703
_reflns_number_gt                6090
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII'

_computing_cell_refinement       'Bruker APEXII'

_computing_data_reduction        'Bruker APEXII'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    
'X-SEED: L.J. Barbour, J. Supramol. Chem. 2001, 1, 189-191 and POV-ray: http://www.povray.org/'

_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.5213P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7703
_refine_ls_number_parameters     493
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.02173(2) 0.72282(2) 0.191019(18) 0.01445(8) Uani 1 1 d . . .
F12 F 0.36195(12) 0.52424(13) 0.52411(10) 0.0276(3) Uani 1 1 d . . .
F8 F 0.16723(12) 0.22084(12) 0.29472(10) 0.0276(3) Uani 1 1 d . . .
F9 F 0.09909(14) 0.19618(13) 0.45160(10) 0.0326(3) Uani 1 1 d . . .
F7 F -0.02354(12) 0.31546(12) 0.35198(10) 0.0272(3) Uani 1 1 d . . .
F4 F -0.59615(12) 1.07819(14) 0.42134(11) 0.0351(4) Uani 1 1 d . . .
N4 N 0.01417(15) 0.71622(16) 0.33590(12) 0.0152(4) Uani 1 1 d . . .
F10 F 0.42420(13) 0.33352(13) 0.51279(12) 0.0402(4) Uani 1 1 d . . .
F11 F 0.27983(13) 0.42155(15) 0.63054(10) 0.0345(4) Uani 1 1 d . . .
N3 N -0.09631(16) 0.73575(16) 0.31431(13) 0.0154(4) Uani 1 1 d . . .
N2 N 0.18613(16) 0.68170(17) 0.12606(13) 0.0177(4) Uani 1 1 d . . .
F5 F -0.56497(13) 1.10590(15) 0.26027(12) 0.0429(4) Uani 1 1 d . . .
N1 N -0.05445(16) 0.75432(16) 0.07602(13) 0.0171(4) Uani 1 1 d . . .
F6 F -0.54466(12) 0.92976(14) 0.32953(13) 0.0385(4) Uani 1 1 d . . .
C30 C 0.07746(18) 0.59275(19) 0.37058(15) 0.0139(4) Uani 1 1 d . . .
C31 C 0.04937(18) 0.49747(19) 0.35618(15) 0.0153(4) Uani 1 1 d . . .
H31 H -0.0142 0.5113 0.3196 0.018 Uiso 1 1 calc R . .
C22 C -0.18057(19) 0.85884(19) 0.32496(15) 0.0160(4) Uani 1 1 d . . .
C23 C -0.1509(2) 0.9485(2) 0.35102(16) 0.0191(5) Uani 1 1 d . . .
H23 H -0.0686 0.9317 0.3560 0.023 Uiso 1 1 calc R . .
C6 C -0.1829(2) 0.7796(2) 0.08782(15) 0.0199(5) Uani 1 1 d . . .
C35 C 0.16949(18) 0.57275(19) 0.42610(15) 0.0157(4) Uani 1 1 d . . .
H35 H 0.1892 0.6376 0.4358 0.019 Uiso 1 1 calc R . .
C33 C 0.20591(19) 0.3609(2) 0.45126(15) 0.0166(4) Uani 1 1 d . . .
H33 H 0.2499 0.2817 0.4783 0.020 Uiso 1 1 calc R . .
F3 F -0.22946(18) 1.25118(15) 0.33013(14) 0.0532(5) Uani 1 1 d . . .
C27 C -0.30169(19) 0.8838(2) 0.31855(15) 0.0180(5) Uani 1 1 d . . .
H27 H -0.3225 0.8233 0.3004 0.022 Uiso 1 1 calc R . .
C12 C 0.28433(19) 0.6226(2) 0.18335(15) 0.0192(5) Uani 1 1 d . . .
C32 C 0.11443(19) 0.38254(19) 0.39528(15) 0.0153(4) Uani 1 1 d . . .
C3 C 0.2161(2) 0.6943(2) 0.02603(16) 0.0191(5) Uani 1 1 d . . .
C34 C 0.23150(19) 0.4573(2) 0.46673(15) 0.0161(4) Uani 1 1 d . . .
F1 F -0.09723(18) 1.11938(16) 0.4135(2) 0.0762(7) Uani 1 1 d . . .
C26 C -0.3917(2) 0.9980(2) 0.33898(16) 0.0199(5) Uani 1 1 d . . .
F2 F -0.2805(2) 1.20561(19) 0.48444(15) 0.0695(6) Uani 1 1 d . . .
C13 C 0.3408(2) 0.4966(2) 0.18904(16) 0.0231(5) Uani 1 1 d . . .
C36 C 0.0890(2) 0.2790(2) 0.37371(16) 0.0198(5) Uani 1 1 d . . .
C17 C 0.3190(2) 0.6931(2) 0.23340(17) 0.0245(5) Uani 1 1 d . . .
C11 C -0.2216(2) 0.6849(2) 0.10779(16) 0.0240(5) Uani 1 1 d . . .
C24 C -0.2417(2) 1.0617(2) 0.36949(17) 0.0224(5) Uani 1 1 d . . .
C29 C -0.5237(2) 1.0268(2) 0.33734(19) 0.0269(5) Uani 1 1 d . . .
C15 C 0.4761(2) 0.5083(3) 0.29069(18) 0.0346(7) Uani 1 1 d . . .
H15 H 0.5435 0.4691 0.3259 0.042 Uiso 1 1 calc R . .
C1 C 0.0070(2) 0.7547(2) -0.01742(16) 0.0192(5) Uani 1 1 d . . .
C25 C -0.3627(2) 1.0879(2) 0.36413(17) 0.0234(5) Uani 1 1 d . . .
H25 H -0.4246 1.1660 0.3774 0.028 Uiso 1 1 calc R . .
C20 C 0.3003(2) 0.4215(2) 0.13820(18) 0.0280(5) Uani 1 1 d . . .
H20A H 0.2107 0.4516 0.1517 0.042 Uiso 1 1 calc R . .
H20B H 0.3355 0.3370 0.1644 0.042 Uiso 1 1 calc R . .
H20C H 0.3285 0.4270 0.0653 0.042 Uiso 1 1 calc R . .
C5 C 0.3486(2) 0.6647(2) -0.02013(17) 0.0251(5) Uani 1 1 d . . .
H5A H 0.3839 0.7011 0.0174 0.038 Uiso 1 1 calc R . .
H5B H 0.3536 0.6969 -0.0906 0.038 Uiso 1 1 calc R . .
H5C H 0.3943 0.5768 -0.0172 0.038 Uiso 1 1 calc R . .
C37 C 0.3243(2) 0.4351(2) 0.53287(17) 0.0206(5) Uani 1 1 d . . .
C2 C 0.1313(2) 0.7327(2) -0.03964(16) 0.0208(5) Uani 1 1 d . . .
H2 H 0.1623 0.7455 -0.1086 0.025 Uiso 1 1 calc R . .
C14 C 0.4373(2) 0.4410(3) 0.24400(17) 0.0307(6) Uani 1 1 d . . .
H14 H 0.4768 0.3553 0.2493 0.037 Uiso 1 1 calc R . .
C21 C 0.2531(2) 0.8282(2) 0.2299(2) 0.0316(6) Uani 1 1 d . . .
H21A H 0.2906 0.8618 0.2679 0.047 Uiso 1 1 calc R . .
H21B H 0.1668 0.8498 0.2599 0.047 Uiso 1 1 calc R . .
H21C H 0.2589 0.8611 0.1597 0.047 Uiso 1 1 calc R . .
C4 C -0.0579(2) 0.7758(2) -0.10628(17) 0.0292(6) Uani 1 1 d . . .
H4A H -0.0935 0.7159 -0.1011 0.044 Uiso 1 1 calc R . .
H4B H 0.0009 0.7678 -0.1691 0.044 Uiso 1 1 calc R . .
H4C H -0.1232 0.8572 -0.1062 0.044 Uiso 1 1 calc R . .
C8 C -0.3895(2) 0.9228(3) 0.08719(19) 0.0362(7) Uani 1 1 d . . .
H8 H -0.4475 1.0037 0.0798 0.043 Uiso 1 1 calc R . .
C16 C 0.4171(2) 0.6326(3) 0.28622(18) 0.0312(6) Uani 1 1 d . . .
H16 H 0.4436 0.6781 0.3197 0.037 Uiso 1 1 calc R . .
C10 C -0.3471(2) 0.7128(3) 0.11708(18) 0.0347(6) Uani 1 1 d . . .
H10 H -0.3758 0.6496 0.1319 0.042 Uiso 1 1 calc R . .
C7 C -0.2660(2) 0.9003(2) 0.07969(17) 0.0265(5) Uani 1 1 d . . .
C19 C -0.1332(2) 0.5554(2) 0.11840(19) 0.0323(6) Uani 1 1 d . . .
H19A H -0.1024 0.5223 0.0519 0.049 Uiso 1 1 calc R . .
H19B H -0.1750 0.5083 0.1624 0.049 Uiso 1 1 calc R . .
H19C H -0.0644 0.5510 0.1479 0.049 Uiso 1 1 calc R . .
C18 C -0.2246(3) 1.0025(2) 0.0665(2) 0.0346(6) Uani 1 1 d . . .
H18A H -0.2955 1.0797 0.0634 0.052 Uiso 1 1 calc R . .
H18B H -0.1658 0.9956 0.0038 0.052 Uiso 1 1 calc R . .
H18C H -0.1854 0.9988 0.1236 0.052 Uiso 1 1 calc R . .
C9 C -0.4290(2) 0.8300(3) 0.10514(19) 0.0416(8) Uani 1 1 d . . .
H9 H -0.5134 0.8472 0.1093 0.050 Uiso 1 1 calc R . .
C28 C -0.2108(2) 1.1579(2) 0.3988(2) 0.0344(6) 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 N2 1.8939(18) . ?
Cu1 N1 1.8940(17) . ?
Cu1 N3 1.9430(17) . ?
Cu1 N4 1.9438(17) . ?
F12 C37 1.326(3) . ?
F8 C36 1.340(2) . ?
F9 C36 1.339(2) . ?
F7 C36 1.336(2) . ?
F4 C29 1.342(3) . ?
N4 N3 1.352(2) . ?
N4 C30 1.435(3) . ?
F10 C37 1.339(3) . ?
F11 C37 1.338(3) . ?
N3 C22 1.430(3) . ?
N2 C3 1.335(3) . ?
N2 C12 1.437(3) . ?
F5 C29 1.342(3) . ?
N1 C1 1.332(3) . ?
N1 C6 1.440(3) . ?
F6 C29 1.332(3) . ?
C30 C31 1.389(3) . ?
C30 C35 1.399(3) . ?
C31 C32 1.381(3) . ?
C31 H31 0.9500 . ?
C22 C23 1.394(3) . ?
C22 C27 1.395(3) . ?
C23 C24 1.381(3) . ?
C23 H23 0.9500 . ?
C6 C11 1.390(3) . ?
C6 C7 1.400(3) . ?
C35 C34 1.385(3) . ?
C35 H35 0.9500 . ?
C33 C34 1.387(3) . ?
C33 C32 1.393(3) . ?
C33 H33 0.9500 . ?
F3 C28 1.333(3) . ?
C27 C26 1.390(3) . ?
C27 H27 0.9500 . ?
C12 C13 1.395(3) . ?
C12 C17 1.405(3) . ?
C32 C36 1.499(3) . ?
C3 C2 1.394(3) . ?
C3 C5 1.510(3) . ?
C34 C37 1.502(3) . ?
F1 C28 1.311(3) . ?
C26 C25 1.388(3) . ?
C26 C29 1.498(3) . ?
F2 C28 1.337(3) . ?
C13 C14 1.398(3) . ?
C13 C20 1.503(3) . ?
C17 C16 1.399(3) . ?
C17 C21 1.500(4) . ?
C11 C10 1.401(3) . ?
C11 C19 1.503(4) . ?
C24 C25 1.386(3) . ?
C24 C28 1.497(3) . ?
C15 C14 1.378(4) . ?
C15 C16 1.379(4) . ?
C15 H15 0.9500 . ?
C1 C2 1.395(3) . ?
C1 C4 1.514(3) . ?
C25 H25 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C2 H2 0.9500 . ?
C14 H14 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C8 C9 1.375(4) . ?
C8 C7 1.395(3) . ?
C8 H8 0.9500 . ?
C16 H16 0.9500 . ?
C10 C9 1.369(4) . ?
C10 H10 0.9500 . ?
C7 C18 1.502(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C9 H9 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
N2 Cu1 N1 99.19(8) . . ?
N2 Cu1 N3 149.63(7) . . ?
N1 Cu1 N3 110.94(7) . . ?
N2 Cu1 N4 109.37(7) . . ?
N1 Cu1 N4 151.41(7) . . ?
N3 Cu1 N4 40.72(7) . . ?
N3 N4 C30 111.59(17) . . ?
N3 N4 Cu1 69.60(10) . . ?
C30 N4 Cu1 108.36(13) . . ?
N4 N3 C22 111.73(17) . . ?
N4 N3 Cu1 69.67(10) . . ?
C22 N3 Cu1 110.15(13) . . ?
C3 N2 C12 117.54(18) . . ?
C3 N2 Cu1 122.18(15) . . ?
C12 N2 Cu1 119.92(13) . . ?
C1 N1 C6 117.77(18) . . ?
C1 N1 Cu1 122.11(15) . . ?
C6 N1 Cu1 120.12(13) . . ?
C31 C30 C35 120.13(19) . . ?
C31 C30 N4 124.58(18) . . ?
C35 C30 N4 115.23(18) . . ?
C32 C31 C30 119.61(19) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C23 C22 C27 119.9(2) . . ?
C23 C22 N3 124.00(19) . . ?
C27 C22 N3 115.78(19) . . ?
C24 C23 C22 119.6(2) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C11 C6 C7 121.7(2) . . ?
C11 C6 N1 119.8(2) . . ?
C7 C6 N1 118.5(2) . . ?
C34 C35 C30 119.3(2) . . ?
C34 C35 H35 120.4 . . ?
C30 C35 H35 120.4 . . ?
C34 C33 C32 118.7(2) . . ?
C34 C33 H33 120.6 . . ?
C32 C33 H33 120.6 . . ?
C26 C27 C22 119.4(2) . . ?
C26 C27 H27 120.3 . . ?
C22 C27 H27 120.3 . . ?
C13 C12 C17 122.1(2) . . ?
C13 C12 N2 118.8(2) . . ?
C17 C12 N2 119.1(2) . . ?
C31 C32 C33 121.1(2) . . ?
C31 C32 C36 119.22(18) . . ?
C33 C32 C36 119.65(19) . . ?
N2 C3 C2 123.5(2) . . ?
N2 C3 C5 119.21(19) . . ?
C2 C3 C5 117.30(19) . . ?
C35 C34 C33 121.14(19) . . ?
C35 C34 C37 120.3(2) . . ?
C33 C34 C37 118.46(19) . . ?
C25 C26 C27 121.1(2) . . ?
C25 C26 C29 117.9(2) . . ?
C27 C26 C29 121.1(2) . . ?
C12 C13 C14 117.8(2) . . ?
C12 C13 C20 121.8(2) . . ?
C14 C13 C20 120.4(2) . . ?
F7 C36 F9 107.30(18) . . ?
F7 C36 F8 106.61(17) . . ?
F9 C36 F8 106.46(18) . . ?
F7 C36 C32 111.96(18) . . ?
F9 C36 C32 112.29(17) . . ?
F8 C36 C32 111.85(18) . . ?
C16 C17 C12 117.5(2) . . ?
C16 C17 C21 121.5(2) . . ?
C12 C17 C21 121.0(2) . . ?
C6 C11 C10 118.2(2) . . ?
C6 C11 C19 122.0(2) . . ?
C10 C11 C19 119.8(2) . . ?
C23 C24 C25 121.3(2) . . ?
C23 C24 C28 119.9(2) . . ?
C25 C24 C28 118.8(2) . . ?
F6 C29 F5 107.0(2) . . ?
F6 C29 F4 106.9(2) . . ?
F5 C29 F4 105.94(19) . . ?
F6 C29 C26 113.13(19) . . ?
F5 C29 C26 111.9(2) . . ?
F4 C29 C26 111.6(2) . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
N1 C1 C2 123.7(2) . . ?
N1 C1 C4 119.6(2) . . ?
C2 C1 C4 116.66(19) . . ?
C24 C25 C26 118.7(2) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
F12 C37 F11 106.50(18) . . ?
F12 C37 F10 107.02(18) . . ?
F11 C37 F10 105.74(18) . . ?
F12 C37 C34 113.06(18) . . ?
F11 C37 C34 111.93(18) . . ?
F10 C37 C34 112.12(18) . . ?
C3 C2 C1 128.5(2) . . ?
C3 C2 H2 115.7 . . ?
C1 C2 H2 115.7 . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C15 C16 C17 121.4(2) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C9 C10 C11 120.8(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C8 C7 C6 117.7(2) . . ?
C8 C7 C18 120.9(2) . . ?
C6 C7 C18 121.3(2) . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C11 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 C18 H18A 109.5 . . ?
C7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C7 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
F1 C28 F3 107.3(2) . . ?
F1 C28 F2 105.7(3) . . ?
F3 C28 F2 105.1(2) . . ?
F1 C28 C24 113.6(2) . . ?
F3 C28 C24 112.2(2) . . ?
F2 C28 C24 112.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_ArFN=ArF
_database_code_depnum_ccdc_archive 'CCDC 1031119'
_audit_update_record             
;
2014-10-27 deposited with the CCDC.
2015-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ArFN=NArF
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H6 F12 N2'
_chemical_formula_sum            'C16 H6 F12 N2'
_chemical_formula_weight         454.20

_journal_name_requested          'Chem. Sci.'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   I41/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   36.710(3)
_cell_length_b                   36.710(3)
_cell_length_c                   4.9148(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6623.4(12)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3632
_cell_measurement_theta_min      4.961
_cell_measurement_theta_max      47.030

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3584
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18954
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.11
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3634
_reflns_number_gt                2173
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII'

_computing_cell_refinement       'Bruker APEXII'

_computing_data_reduction        'Bruker APEXII'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    
'X-SEED: L.J. Barbour, J. Supramol. Chem. 2001, 1, 189-191 and POV-ray: http://www.povray.org/'

_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0947P)²+0.1982P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3634
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1668
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F8 F 0.59924(5) 0.73622(5) 0.0914(4) 0.0396(5) Uani 1 1 d . . .
N2 N 0.61767(6) 0.86003(6) 0.8759(5) 0.0220(5) Uani 1 1 d . . .
F9 F 0.57058(5) 0.74147(5) 0.4691(4) 0.0389(5) Uani 1 1 d . . .
F7 F 0.55876(5) 0.77760(5) 0.1396(4) 0.0418(5) Uani 1 1 d . . .
N1 N 0.64182(6) 0.88127(6) 0.9592(5) 0.0236(6) Uani 1 1 d . . .
F10 F 0.71670(5) 0.79850(7) 0.0217(4) 0.0550(7) Uani 1 1 d . . .
C5 C 0.58597(7) 0.93046(7) 1.4746(6) 0.0211(6) Uani 1 1 d . . .
C8 C 0.54891(8) 0.92925(8) 1.5999(6) 0.0243(7) Uani 1 1 d . . .
C10 C 0.60418(7) 0.81130(7) 0.5698(6) 0.0215(6) Uani 1 1 d . . .
H10 H 0.5804 0.8118 0.6353 0.026 Uiso 1 1 calc R . .
C4 C 0.61024(7) 0.95789(7) 1.5490(6) 0.0226(6) Uani 1 1 d . . .
H4 H 0.6036 0.9753 1.6771 0.027 Uiso 1 1 calc R . .
C12 C 0.64938(7) 0.78530(7) 0.2714(6) 0.0206(6) Uani 1 1 d . . .
H12 H 0.6559 0.7685 0.1383 0.025 Uiso 1 1 calc R . .
C3 C 0.64451(8) 0.95878(7) 1.4285(6) 0.0225(6) Uani 1 1 d . . .
F12 F 0.73085(7) 0.83896(7) 0.3047(7) 0.0976(12) Uani 1 1 d . . .
C1 C 0.62951(7) 0.90610(7) 1.1621(6) 0.0197(6) Uani 1 1 d . . .
C13 C 0.67497(8) 0.81000(7) 0.3758(6) 0.0216(6) Uani 1 1 d . . .
C9 C 0.62993(7) 0.83548(7) 0.6711(6) 0.0206(6) Uani 1 1 d . . .
C11 C 0.61393(7) 0.78647(7) 0.3714(6) 0.0204(6) Uani 1 1 d . . .
C7 C 0.67019(9) 0.98885(8) 1.5040(7) 0.0297(7) Uani 1 1 d . . .
C16 C 0.71363(8) 0.80787(8) 0.2775(7) 0.0270(7) Uani 1 1 d . . .
C15 C 0.58559(8) 0.76043(8) 0.2678(6) 0.0244(7) Uani 1 1 d . . .
C6 C 0.59502(7) 0.90497(7) 1.2815(6) 0.0204(6) Uani 1 1 d . . .
H6 H 0.5784 0.8871 1.2307 0.024 Uiso 1 1 calc R . .
C14 C 0.66567(7) 0.83475(7) 0.5725(6) 0.0208(6) Uani 1 1 d . . .
H14 H 0.6830 0.8509 0.6400 0.025 Uiso 1 1 calc R . .
F11 F 0.73294(6) 0.78436(9) 0.4139(6) 0.0903(11) Uani 1 1 d . . .
C2 C 0.65435(7) 0.93297(7) 1.2375(6) 0.0233(7) Uani 1 1 d . . .
H2 H 0.6774 0.9335 1.1596 0.028 Uiso 1 1 calc R . .
F6 F 0.53856(6) 0.89483(5) 1.6492(5) 0.0548(7) Uani 1 1 d . . .
F4 F 0.52345(5) 0.94326(6) 1.4416(4) 0.0477(6) Uani 1 1 d . . .
F5 F 0.54684(5) 0.94646(5) 1.8368(4) 0.0386(5) Uani 1 1 d . . .
F3 F 0.67589(8) 0.99089(7) 1.7697(5) 0.0756(9) Uani 1 1 d . . .
F2 F 0.70274(5) 0.98524(5) 1.3917(5) 0.0477(6) Uani 1 1 d . . .
F1 F 0.65807(5) 1.02129(5) 1.4230(6) 0.0530(7) 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
F8 C15 1.339(3) . ?
N2 N1 1.250(3) . ?
N2 C9 1.424(4) . ?
F9 C15 1.329(4) . ?
F7 C15 1.328(3) . ?
N1 C1 1.425(4) . ?
F10 C16 1.308(4) . ?
C5 C6 1.374(4) . ?
C5 C4 1.393(4) . ?
C5 C8 1.494(4) . ?
C8 F4 1.320(3) . ?
C8 F5 1.327(3) . ?
C8 F6 1.341(3) . ?
C10 C11 1.382(4) . ?
C10 C9 1.389(4) . ?
C4 C3 1.391(4) . ?
C12 C11 1.392(4) . ?
C12 C13 1.403(4) . ?
C3 C2 1.382(4) . ?
C3 C7 1.498(4) . ?
F12 C16 1.311(4) . ?
C1 C2 1.393(4) . ?
C1 C6 1.396(4) . ?
C13 C14 1.370(4) . ?
C13 C16 1.501(4) . ?
C9 C14 1.399(4) . ?
C11 C15 1.502(4) . ?
C7 F2 1.323(4) . ?
C7 F3 1.325(4) . ?
C7 F1 1.332(4) . ?
C16 F11 1.303(4) . ?

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 N2 C9 113.7(2) . . ?
N2 N1 C1 113.8(2) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 C8 119.0(2) . . ?
C4 C5 C8 119.7(3) . . ?
F4 C8 F5 106.9(2) . . ?
F4 C8 F6 105.8(3) . . ?
F5 C8 F6 105.9(3) . . ?
F4 C8 C5 113.0(3) . . ?
F5 C8 C5 113.5(2) . . ?
F6 C8 C5 111.1(2) . . ?
C11 C10 C9 119.9(3) . . ?
C3 C4 C5 118.9(3) . . ?
C11 C12 C13 118.5(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 C7 120.6(3) . . ?
C4 C3 C7 118.8(3) . . ?
C2 C1 C6 120.2(3) . . ?
C2 C1 N1 115.6(2) . . ?
C6 C1 N1 124.2(2) . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 C16 119.8(3) . . ?
C12 C13 C16 118.8(3) . . ?
C10 C9 C14 120.1(3) . . ?
C10 C9 N2 116.3(2) . . ?
C14 C9 N2 123.6(2) . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 C15 118.7(3) . . ?
C12 C11 C15 120.5(3) . . ?
F2 C7 F3 105.9(3) . . ?
F2 C7 F1 105.4(3) . . ?
F3 C7 F1 107.3(3) . . ?
F2 C7 C3 113.0(3) . . ?
F3 C7 C3 112.7(3) . . ?
F1 C7 C3 112.0(3) . . ?
F11 C16 F10 105.9(3) . . ?
F11 C16 F12 105.2(3) . . ?
F10 C16 F12 106.6(3) . . ?
F11 C16 C13 112.5(3) . . ?
F10 C16 C13 113.8(3) . . ?
F12 C16 C13 112.2(3) . . ?
F7 C15 F9 107.1(2) . . ?
F7 C15 F8 106.6(2) . . ?
F9 C15 F8 106.8(2) . . ?
F7 C15 C11 111.9(2) . . ?
F9 C15 C11 111.6(3) . . ?
F8 C15 C11 112.5(2) . . ?
C5 C6 C1 119.3(3) . . ?
C13 C14 C9 119.4(3) . . ?
C3 C2 C1 119.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.075
