# Electronic Supplementary Material (ESI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_111
_database_code_depnum_ccdc_archive 'CCDC 1486884'
_audit_update_record             
;
2016-06-21 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'BP4VA FI-1'
_chemical_name_common            4FI-1
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 N2, 2(C6 F3 I3)'
_chemical_formula_sum            'C20 H10 F3 I3 N'
_chemical_formula_weight         701.99

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   8.6902(17)
_cell_length_b                   13.870(3)
_cell_length_c                   17.377(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.80(3)
_cell_angle_gamma                90.00
_cell_volume                     2042.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15060
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1292
_exptl_absorpt_coefficient_mu    4.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5639
_exptl_absorpt_correction_T_max  0.6304
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18046
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4648
_reflns_number_gt                3413
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97

_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)+(0.0777P)²+3.4087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4648
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3030(7) 0.6937(5) 0.3686(4) 0.0466(13) Uani 1 1 d . . .
C2 C 0.2531(7) 0.7235(5) 0.4356(4) 0.0492(14) Uani 1 1 d . . .
C3 C 0.3339(8) 0.7919(4) 0.4869(4) 0.0473(14) Uani 1 1 d . . .
C4 C 0.4722(8) 0.8279(4) 0.4703(4) 0.0476(14) Uani 1 1 d . . .
C5 C 0.5267(7) 0.8002(5) 0.4057(4) 0.0481(14) Uani 1 1 d . . .
C6 C 0.4401(8) 0.7340(5) 0.3554(3) 0.0515(15) Uani 1 1 d . . .
C7 C 0.5509(7) 0.5712(5) 0.5588(4) 0.0467(13) Uani 1 1 d . . .
C8 C 0.6043(9) 0.6462(5) 0.6162(5) 0.0604(18) Uani 1 1 d . . .
H8 H 0.5482 0.6594 0.6548 0.072 Uiso 1 1 calc R . .
C9 C 0.7366(9) 0.6975(6) 0.6139(5) 0.0667(19) Uani 1 1 d . . .
H9 H 0.7682 0.7471 0.6500 0.080 Uiso 1 1 calc R . .
C10 C 0.8269(9) 0.6764(7) 0.5574(5) 0.069(2) Uani 1 1 d . . .
H10 H 0.9173 0.7119 0.5568 0.083 Uiso 1 1 calc R . .
C11 C 0.7821(8) 0.6045(6) 0.5043(5) 0.0644(19) Uani 1 1 d . . .
H11 H 0.8457 0.5899 0.4693 0.077 Uiso 1 1 calc R . .
C12 C 0.6402(8) 0.5505(5) 0.5002(4) 0.0495(14) Uani 1 1 d . . .
C13 C 0.5894(7) 0.4812(5) 0.4426(4) 0.0484(14) Uani 1 1 d . . .
C14 C 0.6884(8) 0.4619(6) 0.3849(4) 0.0578(17) Uani 1 1 d . . .
H14 H 0.7889 0.4372 0.4046 0.069 Uiso 1 1 calc R . .
C15 C 0.6467(8) 0.4766(5) 0.3081(4) 0.0565(16) Uani 1 1 d . . .
H15 H 0.5463 0.5008 0.2873 0.068 Uiso 1 1 calc R . .
C16 C 0.7519(7) 0.4565(5) 0.2533(4) 0.0484(14) Uani 1 1 d . . .
C17 C 0.8683(8) 0.3865(5) 0.2701(4) 0.0545(15) Uani 1 1 d . . .
H17 H 0.8800 0.3483 0.3150 0.065 Uiso 1 1 calc R . .
C18 C 0.9659(9) 0.3753(6) 0.2186(5) 0.0642(19) Uani 1 1 d . . .
H18 H 1.0413 0.3267 0.2297 0.077 Uiso 1 1 calc R . .
C19 C 0.8458(10) 0.4928(6) 0.1369(4) 0.065(2) Uani 1 1 d . . .
H19 H 0.8363 0.5288 0.0909 0.078 Uiso 1 1 calc R . .
C20 C 0.7396(9) 0.5091(6) 0.1836(4) 0.0621(18) Uani 1 1 d . . .
H20 H 0.6603 0.5549 0.1689 0.075 Uiso 1 1 calc R . .
F1 F 0.1198(5) 0.6862(3) 0.4496(3) 0.0657(11) Uani 1 1 d . . .
F2 F 0.5522(5) 0.8944(3) 0.5194(3) 0.0675(11) Uani 1 1 d . . .
F3 F 0.4899(5) 0.7069(3) 0.2909(2) 0.0682(11) Uani 1 1 d . . .
I1 I 0.17283(6) 0.59410(4) 0.29087(3) 0.06715(18) Uani 1 1 d . . .
I2 I 0.25724(7) 0.83622(4) 0.58618(3) 0.07011(19) Uani 1 1 d . . .
I3 I 0.73702(6) 0.85957(4) 0.38555(3) 0.06090(17) Uani 1 1 d . . .
N1 N 0.9620(7) 0.4278(5) 0.1543(4) 0.0654(16) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.380(9) . ?
C1 C2 1.392(9) . ?
C1 I1 2.082(6) . ?
C2 F1 1.339(7) . ?
C2 C3 1.381(9) . ?
C3 C4 1.390(9) . ?
C3 I2 2.076(6) . ?
C4 F2 1.342(7) . ?
C4 C5 1.365(9) . ?
C5 C6 1.373(9) . ?
C5 I3 2.104(6) . ?
C6 F3 1.341(7) . ?
C7 C13 1.416(9) 3_666 ?
C7 C12 1.440(8) . ?
C7 C8 1.446(10) . ?
C8 C9 1.360(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.417(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.356(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.431(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(10) . ?
C13 C7 1.416(9) 3_666 ?
C13 C14 1.484(8) . ?
C14 C15 1.318(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.486(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(9) . ?
C16 C20 1.398(9) . ?
C17 C18 1.370(10) . ?
C17 H17 0.9300 . ?
C18 N1 1.328(10) . ?
C18 H18 0.9300 . ?
C19 N1 1.338(10) . ?
C19 C20 1.376(10) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
C6 C1 C2 117.3(6) . . ?
C6 C1 I1 121.7(5) . . ?
C2 C1 I1 120.9(5) . . ?
F1 C2 C3 118.9(6) . . ?
F1 C2 C1 118.7(6) . . ?
C3 C2 C1 122.4(6) . . ?
C2 C3 C4 116.9(6) . . ?
C2 C3 I2 121.9(5) . . ?
C4 C3 I2 121.2(5) . . ?
F2 C4 C5 119.4(6) . . ?
F2 C4 C3 117.7(6) . . ?
C5 C4 C3 122.8(6) . . ?
C4 C5 C6 118.1(6) . . ?
C4 C5 I3 119.9(5) . . ?
C6 C5 I3 122.0(5) . . ?
F3 C6 C5 119.2(6) . . ?
F3 C6 C1 118.4(6) . . ?
C5 C6 C1 122.4(6) . . ?
C13 C7 C12 118.9(6) 3_666 . ?
C13 C7 C8 121.7(6) 3_666 . ?
C12 C7 C8 119.4(6) . . ?
C9 C8 C7 120.0(7) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.9(8) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 120.3(7) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 122.2(7) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 122.1(6) . . ?
C13 C12 C7 120.9(6) . . ?
C11 C12 C7 117.0(7) . . ?
C12 C13 C7 120.2(5) . 3_666 ?
C12 C13 C14 118.3(6) . . ?
C7 C13 C14 121.5(6) 3_666 . ?
C15 C14 C13 125.8(6) . . ?
C15 C14 H14 117.1 . . ?
C13 C14 H14 117.1 . . ?
C14 C15 C16 123.3(6) . . ?
C14 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
C17 C16 C20 117.4(6) . . ?
C17 C16 C15 121.4(6) . . ?
C20 C16 C15 121.2(6) . . ?
C18 C17 C16 118.1(7) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
N1 C18 C17 125.6(7) . . ?
N1 C18 H18 117.2 . . ?
C17 C18 H18 117.2 . . ?
N1 C19 C20 123.3(7) . . ?
N1 C19 H19 118.4 . . ?
C20 C19 H19 118.4 . . ?
C19 C20 C16 119.5(7) . . ?
C19 C20 H20 120.2 . . ?
C16 C20 H20 120.2 . . ?
C18 N1 C19 115.9(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F1 179.5(6) . . . . ?
I1 C1 C2 F1 0.6(8) . . . . ?
C6 C1 C2 C3 1.2(10) . . . . ?
I1 C1 C2 C3 -177.8(5) . . . . ?
F1 C2 C3 C4 179.5(6) . . . . ?
C1 C2 C3 C4 -2.2(10) . . . . ?
F1 C2 C3 I2 1.3(8) . . . . ?
C1 C2 C3 I2 179.6(5) . . . . ?
C2 C3 C4 F2 180.0(6) . . . . ?
I2 C3 C4 F2 -1.8(8) . . . . ?
C2 C3 C4 C5 1.5(10) . . . . ?
I2 C3 C4 C5 179.7(5) . . . . ?
F2 C4 C5 C6 -178.3(6) . . . . ?
C3 C4 C5 C6 0.1(10) . . . . ?
F2 C4 C5 I3 1.3(9) . . . . ?
C3 C4 C5 I3 179.7(5) . . . . ?
C4 C5 C6 F3 178.8(6) . . . . ?
I3 C5 C6 F3 -0.8(9) . . . . ?
C4 C5 C6 C1 -1.2(10) . . . . ?
I3 C5 C6 C1 179.2(5) . . . . ?
C2 C1 C6 F3 -179.4(6) . . . . ?
I1 C1 C6 F3 -0.5(9) . . . . ?
C2 C1 C6 C5 0.6(10) . . . . ?
I1 C1 C6 C5 179.5(5) . . . . ?
C13 C7 C8 C9 -177.5(7) 3_666 . . . ?
C12 C7 C8 C9 0.9(10) . . . . ?
C7 C8 C9 C10 -2.2(11) . . . . ?
C8 C9 C10 C11 0.3(13) . . . . ?
C9 C10 C11 C12 3.0(12) . . . . ?
C10 C11 C12 C13 175.8(7) . . . . ?
C10 C11 C12 C7 -4.1(11) . . . . ?
C13 C7 C12 C13 0.7(10) 3_666 . . . ?
C8 C7 C12 C13 -177.8(6) . . . . ?
C13 C7 C12 C11 -179.4(6) 3_666 . . . ?
C8 C7 C12 C11 2.1(9) . . . . ?
C11 C12 C13 C7 179.4(6) . . . 3_666 ?
C7 C12 C13 C7 -0.7(11) . . . 3_666 ?
C11 C12 C13 C14 1.3(10) . . . . ?
C7 C12 C13 C14 -178.8(6) . . . . ?
C12 C13 C14 C15 -116.4(9) . . . . ?
C7 C13 C14 C15 65.5(11) 3_666 . . . ?
C13 C14 C15 C16 179.5(7) . . . . ?
C14 C15 C16 C17 27.6(12) . . . . ?
C14 C15 C16 C20 -150.8(8) . . . . ?
C20 C16 C17 C18 1.6(11) . . . . ?
C15 C16 C17 C18 -176.8(7) . . . . ?
C16 C17 C18 N1 2.0(13) . . . . ?
N1 C19 C20 C16 0.4(13) . . . . ?
C17 C16 C20 C19 -2.7(11) . . . . ?
C15 C16 C20 C19 175.7(7) . . . . ?
C17 C18 N1 C19 -4.3(13) . . . . ?
C20 C19 N1 C18 3.0(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         2.177
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.150
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method THF
_chemical_properties_physical    ', Efflorescent'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_3f3i-4-2
_database_code_depnum_ccdc_archive 'CCDC 1486885'
_audit_update_record             
;
2016-06-21 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'BP4VA FI-2'
_chemical_name_common            4FI-2
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 N2, 2(C6 F3 I3)'
_chemical_formula_sum            'C40 H20 F6 I6 N2'
_chemical_formula_weight         1403.98

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   5.1420(10)
_cell_length_b                   12.724(3)
_cell_length_c                   16.436(3)
_cell_angle_alpha                109.15(3)
_cell_angle_beta                 96.00(3)
_cell_angle_gamma                93.79(3)
_cell_volume                     1004.5(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8669
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      27.67

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             646
_exptl_absorpt_coefficient_mu    4.699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5591
_exptl_absorpt_correction_T_max  0.6260
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9853
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4537
_reflns_number_gt                3719
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97

_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)+(0.0279P)²+2.1660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4537
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0815
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2729(8) 0.9376(4) 0.2501(3) 0.0413(10) Uani 1 1 d . . .
C2 C 0.1110(9) 0.8629(4) 0.2724(3) 0.0449(10) Uani 1 1 d . . .
C3 C -0.0896(9) 0.7984(4) 0.2090(3) 0.0434(10) Uani 1 1 d . . .
C4 C -0.1329(8) 0.8058(4) 0.1271(3) 0.0396(9) Uani 1 1 d . . .
C5 C 0.0357(9) 0.8824(4) 0.1094(3) 0.0417(10) Uani 1 1 d . . .
C6 C 0.2370(9) 0.9504(3) 0.1705(3) 0.0399(9) Uani 1 1 d . . .
C7 C 0.9277(8) 0.3902(3) 0.4417(2) 0.0330(8) Uani 1 1 d . . .
C8 C 1.1506(7) 0.4132(3) 0.5087(2) 0.0312(8) Uani 1 1 d . . .
C9 C 1.3023(9) 0.3232(4) 0.5092(3) 0.0413(10) Uani 1 1 d . . .
H9 H 1.4508 0.3373 0.5502 0.050 Uiso 1 1 calc R . .
C10 C 1.2382(10) 0.2192(4) 0.4527(3) 0.0489(11) Uani 1 1 d . . .
H10 H 1.3410 0.1626 0.4552 0.059 Uiso 1 1 calc R . .
C11 C 1.0140(10) 0.1952(4) 0.3891(3) 0.0496(11) Uani 1 1 d . . .
H11 H 0.9677 0.1225 0.3511 0.060 Uiso 1 1 calc R . .
C12 C 0.8682(8) 0.2766(4) 0.3832(3) 0.0416(10) Uani 1 1 d . . .
H12 H 0.7243 0.2591 0.3401 0.050 Uiso 1 1 calc R . .
C13 C 0.7815(7) 0.4764(4) 0.4328(3) 0.0332(8) Uani 1 1 d . . .
C14 C 0.5565(8) 0.4473(4) 0.3627(3) 0.0382(9) Uani 1 1 d . . .
H14 H 0.4312 0.3901 0.3607 0.046 Uiso 1 1 calc R . .
C15 C 0.5163(8) 0.4950(4) 0.3026(3) 0.0408(10) Uani 1 1 d . . .
H15 H 0.6397 0.5527 0.3041 0.049 Uiso 1 1 calc R . .
C16 C 0.2894(7) 0.4629(3) 0.2332(3) 0.0342(8) Uani 1 1 d . . .
C17 C 0.1227(10) 0.3655(4) 0.2131(3) 0.0512(12) Uani 1 1 d . . .
H17 H 0.1493 0.3164 0.2437 0.061 Uiso 1 1 calc R . .
C18 C -0.0841(10) 0.3422(5) 0.1468(3) 0.0609(15) Uani 1 1 d . . .
H18 H -0.1930 0.2760 0.1341 0.073 Uiso 1 1 calc R . .
C19 C 0.0219(10) 0.4991(4) 0.1190(3) 0.0522(12) Uani 1 1 d . . .
H19 H -0.0085 0.5457 0.0864 0.063 Uiso 1 1 calc R . .
C20 C 0.2330(10) 0.5306(4) 0.1844(3) 0.0510(12) Uani 1 1 d . . .
H20 H 0.3375 0.5975 0.1956 0.061 Uiso 1 1 calc R . .
F1 F 0.4735(6) 0.9997(2) 0.31013(18) 0.0593(8) Uani 1 1 d . . .
F2 F -0.2530(6) 0.7277(3) 0.2299(2) 0.0632(8) Uani 1 1 d . . .
F3 F 0.0005(6) 0.8929(3) 0.03096(18) 0.0593(8) Uani 1 1 d . . .
I1 I 0.15920(10) 0.84894(4) 0.39530(3) 0.08026(15) Uani 1 1 d . . .
I2 I -0.43853(6) 0.70518(3) 0.03258(2) 0.04692(10) Uani 1 1 d . . .
I3 I 0.47441(8) 1.06804(3) 0.14130(3) 0.06635(13) Uani 1 1 d . . .
N1 N -0.1387(7) 0.4069(3) 0.1002(3) 0.0485(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.353(5) . ?
C1 C6 1.365(6) . ?
C1 C2 1.386(6) . ?
C2 C3 1.387(6) . ?
C2 I1 2.076(5) . ?
C3 F2 1.341(5) . ?
C3 C4 1.375(6) . ?
C4 C5 1.383(6) . ?
C4 I2 2.107(4) . ?
C5 F3 1.335(5) . ?
C5 C6 1.387(6) . ?
C6 I3 2.078(4) . ?
C7 C13 1.407(6) . ?
C7 C12 1.441(6) . ?
C7 C8 1.446(5) . ?
C8 C13 1.413(6) 2_766 ?
C8 C9 1.430(6) . ?
C9 C10 1.339(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.417(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.340(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C8 1.413(6) 2_766 ?
C13 C14 1.479(5) . ?
C14 C15 1.325(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.477(5) . ?
C15 H15 0.9300 . ?
C16 C20 1.380(6) . ?
C16 C17 1.383(6) . ?
C17 C18 1.382(6) . ?
C17 H17 0.9300 . ?
C18 N1 1.319(7) . ?
C18 H18 0.9300 . ?
C19 N1 1.317(6) . ?
C19 C20 1.382(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
F1 C1 C6 119.5(4) . . ?
F1 C1 C2 118.0(4) . . ?
C6 C1 C2 122.5(4) . . ?
C1 C2 C3 116.9(4) . . ?
C1 C2 I1 122.0(3) . . ?
C3 C2 I1 121.1(3) . . ?
F2 C3 C4 118.7(4) . . ?
F2 C3 C2 117.8(4) . . ?
C4 C3 C2 123.4(4) . . ?
C3 C4 C5 116.6(4) . . ?
C3 C4 I2 122.0(3) . . ?
C5 C4 I2 121.4(3) . . ?
F3 C5 C4 118.8(4) . . ?
F3 C5 C6 118.6(4) . . ?
C4 C5 C6 122.6(4) . . ?
C1 C6 C5 117.9(4) . . ?
C1 C6 I3 121.4(3) . . ?
C5 C6 I3 120.7(3) . . ?
C13 C7 C12 121.8(4) . . ?
C13 C7 C8 121.0(4) . . ?
C12 C7 C8 117.2(4) . . ?
C13 C8 C9 122.8(3) 2_766 . ?
C13 C8 C7 119.4(4) 2_766 . ?
C9 C8 C7 117.7(4) . . ?
C10 C9 C8 122.4(4) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 122.0(4) . . ?
C11 C12 H12 119.0 . . ?
C7 C12 H12 119.0 . . ?
C7 C13 C8 119.7(3) . 2_766 ?
C7 C13 C14 118.3(4) . . ?
C8 C13 C14 122.1(4) 2_766 . ?
C15 C14 C13 126.3(4) . . ?
C15 C14 H14 116.9 . . ?
C13 C14 H14 116.9 . . ?
C14 C15 C16 124.6(4) . . ?
C14 C15 H15 117.7 . . ?
C16 C15 H15 117.7 . . ?
C20 C16 C17 116.2(4) . . ?
C20 C16 C15 120.8(4) . . ?
C17 C16 C15 123.0(4) . . ?
C18 C17 C16 119.0(4) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
N1 C18 C17 124.9(5) . . ?
N1 C18 H18 117.5 . . ?
C17 C18 H18 117.5 . . ?
N1 C19 C20 123.7(5) . . ?
N1 C19 H19 118.1 . . ?
C20 C19 H19 118.1 . . ?
C16 C20 C19 120.2(4) . . ?
C16 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C19 N1 C18 116.0(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 -178.6(4) . . . . ?
C6 C1 C2 C3 1.3(7) . . . . ?
F1 C1 C2 I1 2.5(6) . . . . ?
C6 C1 C2 I1 -177.5(4) . . . . ?
C1 C2 C3 F2 -178.2(4) . . . . ?
I1 C2 C3 F2 0.7(6) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
I1 C2 C3 C4 178.8(4) . . . . ?
F2 C3 C4 C5 178.0(4) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
F2 C3 C4 I2 -2.3(6) . . . . ?
C2 C3 C4 I2 179.5(4) . . . . ?
C3 C4 C5 F3 -179.6(4) . . . . ?
I2 C4 C5 F3 0.7(6) . . . . ?
C3 C4 C5 C6 -0.9(7) . . . . ?
I2 C4 C5 C6 179.4(3) . . . . ?
F1 C1 C6 C5 177.6(4) . . . . ?
C2 C1 C6 C5 -2.4(7) . . . . ?
F1 C1 C6 I3 -2.6(6) . . . . ?
C2 C1 C6 I3 177.4(4) . . . . ?
F3 C5 C6 C1 -179.1(4) . . . . ?
C4 C5 C6 C1 2.2(7) . . . . ?
F3 C5 C6 I3 1.1(6) . . . . ?
C4 C5 C6 I3 -177.6(3) . . . . ?
C13 C7 C8 C13 1.4(6) . . . 2_766 ?
C12 C7 C8 C13 179.5(4) . . . 2_766 ?
C13 C7 C8 C9 -175.0(4) . . . . ?
C12 C7 C8 C9 3.0(6) . . . . ?
C13 C8 C9 C10 -179.1(4) 2_766 . . . ?
C7 C8 C9 C10 -2.8(6) . . . . ?
C8 C9 C10 C11 0.4(8) . . . . ?
C9 C10 C11 C12 1.8(8) . . . . ?
C10 C11 C12 C7 -1.4(8) . . . . ?
C13 C7 C12 C11 177.0(4) . . . . ?
C8 C7 C12 C11 -1.0(7) . . . . ?
C12 C7 C13 C8 -179.4(4) . . . 2_766 ?
C8 C7 C13 C8 -1.4(6) . . . 2_766 ?
C12 C7 C13 C14 1.8(6) . . . . ?
C8 C7 C13 C14 179.8(4) . . . . ?
C7 C13 C14 C15 -126.7(5) . . . . ?
C8 C13 C14 C15 54.5(6) 2_766 . . . ?
C13 C14 C15 C16 179.6(4) . . . . ?
C14 C15 C16 C20 166.7(5) . . . . ?
C14 C15 C16 C17 -13.4(8) . . . . ?
C20 C16 C17 C18 0.3(8) . . . . ?
C15 C16 C17 C18 -179.7(5) . . . . ?
C16 C17 C18 N1 -0.4(9) . . . . ?
C17 C16 C20 C19 -0.7(8) . . . . ?
C15 C16 C20 C19 179.3(5) . . . . ?
N1 C19 C20 C16 1.4(9) . . . . ?
C20 C19 N1 C18 -1.5(8) . . . . ?
C17 C18 N1 C19 1.0(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         1.590
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.105
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'THF and ethanol'
_chemical_properties_physical    ', Efflorescent'
_exptl_crystal_preparation       ', Luminescent'
