# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1b
#TrackingRef '1b.cif'


#============================================================================
# start Validation Reply Form

_vrf_PLAT029_1b                  
;
PROBLEM: Alert B - _diffrn_measured_fraction_theta_full Low ....... 0.94
RESPONSE: The available crystals of compound 1b diffracted very weakly at
high angle due to a combination of several factors: i) being an organic
compound with only low-weight elements; ii) very large unit cell (the
maximum dimension of one of the axis is over 46 A); iii) solvent disorder;
iv) large voids with smeared-out electron density.
Therefore, even though data was collected to high angle, reflections near
and above 0.83 A of resolution were of very weak intensity (below the
2s(I) treshold) and could not be properly integrated.
Collection of a full data set may only be possible using a rotating anode
or a synchrotron source.
;

_vrf_REFLT03_1b                  
;
PROBLEM: Alert C - Reflection count < 95% complete
RESPONSE: Please see our response to _vrf_PLAT029_1b.
;

_vrf_PLAT022_1b                  
;
PROBLEM: Alert C - Ratio Unique / Expected Reflections too Low .... 0.95
RESPONSE: Please see our response to _vrf_PLAT029_1b.
;

_vrf_PLAT220_1b                  
;
PROBLEM: Alert C - Large Non-Solvent C Ueq(max)/Ueq(min) ...2.60 Ratio
RESPONSE: Even at the low temperature of 100 K, molecule 1b has markedly
distinct degrees of freedom for each type of carbon atom: those composing
the terminal groups of the substituent side arms are severely affected
by thermal disorder, leading to drastically distinct Ueq values when
compared with those of the central ring.
;

_vrf_PLAT222_1b                  
;
PROBLEM: Alert C - Large Non-Solvent H Ueq(max)/Ueq(min) ...3.09 Ratio
RESPONSE: Please see our response to _vrf_PLAT220_1b.
;

_vrf_PLAT250_1b                  
;
PROBLEM: Alert C - Large U3/U1 Ratio for Average U(i,j) Tensor ....3.05
RESPONSE: Please see our response to _vrf_PLAT220_1b.
;

_vrf_PLAT244_1b                  
;
PROBLEM: Alert C - Low 'Solvent' Ueq as Compared to Neighbors for C19
RESPONSE: Please see our response to _vrf_PLAT220_1b.
;

_vrf_PLAT952_1b                  
;
PROBLEM: Alert C - Reported and Calculated Lmax Values Differ by..3
RESPONSE: Please see our response to _vrf_PLAT029_1b.
;

_vrf_PLAT860_1b                  
;
PROBLEM: Alert G - Note: Number of Least-Squares Restraints ..... 2
RESPONSE: As described in the main paper, some hydrogen atoms associated
with the nitrogen atoms were directly located from difference Fourier
maps and included in the final structural model with restrained N---H
distances.
;

_vrf_PLAT302_1b                  
;
PROBLEM: Alert G - Note Anion/Solvent Disorder
RESPONSE: Each molecule of 1b is diprotonated with two charge-balancing
fluoride anions, and corresponding H+ moieties, being statistically
distributed among the four side arms of the molecule (with fixed rate
of occupancy of 50%). Please see main paper for further details.
;


_vrf_PLAT605_1b                  
;
PROBLEM: Alert G - Structure Contains Solvent Accessible VOIDS
RESPONSE: The structural model presented was obtained after treating the
original data with the SQUEEZE subroutines implemented in the software
package PLATON: voids should contain highly disordered solvent molecules
which could not be located from difference Fourier maps. Further details
on this treatment are provided in the technical section of the main
paper.
;


# end Validation Reply Form
# =========================================================================



# =======================================================================

_audit_creation_method           'SHELXL-97, manual editing plus enCIFer'
_audit_creation_date             '14 May 2009'

# =======================================================================

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C64 H56 F16 N12, 2(C H Cl3), 2(F)'
_chemical_formula_sum            'C66 H58 Cl6 F18 N12'
_chemical_formula_weight         1573.94

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'F d d d'
_symmetry_space_group_name_Hall  '-F 2uv 2vw'


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

_cell_length_a                   14.6651(15)
_cell_length_b                   25.318(3)
_cell_length_c                   46.706(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     17341(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2591
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      20.44

_exptl_crystal_description       Needle
_exptl_crystal_colour            Purple
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             6416
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9465
_exptl_absorpt_correction_T_max  0.9621
_exptl_absorpt_process_details   
;
SADABS (Sheldrick, 1997)
;

_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  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'omega/phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25756
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0835
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         25.32
_reflns_number_total             3759
_reflns_number_gt                1964
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 '
_computing_data_reduction        'SAINT+ (Bruker, 1997-2005)'
_computing_structure_solution    'SHELXTL (Bruker 2001)'
_computing_structure_refinement  'SHELXTL '
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXTL '

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1722P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3759
_refine_ls_number_parameters     256
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1629
_refine_ls_R_factor_gt           0.0887
_refine_ls_wR_factor_ref         0.2886
_refine_ls_wR_factor_gt          0.2558
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.046
_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
C1 C 0.6175(3) 0.29276(19) 1.11076(10) 0.0444(12) Uani 1 1 d . . .
H1 H 0.6101 0.3231 1.0991 0.053 Uiso 1 1 calc R . .
C2 C 0.6145(3) 0.23869(18) 1.10116(10) 0.0381(12) Uani 1 1 d . . .
C3 C 0.6062(3) 0.22041(18) 1.07332(10) 0.0352(12) Uani 1 1 d . . .
C4 C 0.6149(3) 0.16751(18) 1.06445(10) 0.0351(11) Uani 1 1 d . . .
C5 C 0.6172(3) 0.15077(17) 1.03479(10) 0.0364(11) Uani 1 1 d . . .
H5 H 0.6092 0.1726 1.0184 0.044 Uiso 1 1 calc R . .
C6 C 0.5891(3) 0.26054(18) 1.05055(10) 0.0383(12) Uani 1 1 d . . .
C7 C 0.6567(3) 0.2857(2) 1.03559(11) 0.0482(13) Uani 1 1 d . . .
C8 C 0.6413(3) 0.3215(2) 1.01403(11) 0.0536(15) Uani 1 1 d . . .
C9 C 0.5535(3) 0.33504(18) 1.00531(10) 0.0403(12) Uani 1 1 d . . .
C10 C 0.4847(3) 0.30898(18) 1.02062(11) 0.0417(12) Uani 1 1 d . . .
C11 C 0.5018(3) 0.27401(17) 1.04207(10) 0.0367(12) Uani 1 1 d . . .
C13 C 0.5906(4) 0.3977(2) 0.96509(12) 0.0558(15) Uani 1 1 d . . .
H13A H 0.6432 0.4112 0.9762 0.067 Uiso 1 1 calc R . .
H13B H 0.5581 0.4285 0.9570 0.067 Uiso 1 1 calc R . .
C14 C 0.6258(3) 0.3641(2) 0.94084(11) 0.0541(15) Uani 1 1 d . . .
H14A H 0.6707 0.3845 0.9295 0.065 Uiso 1 1 calc R . .
H14B H 0.6570 0.3326 0.9487 0.065 Uiso 1 1 calc R . .
C16 C 0.5682(3) 0.3192(3) 0.90098(14) 0.0648(16) Uani 1 1 d . . .
C17 C 0.6615(4) 0.3014(3) 0.89203(14) 0.083(2) Uani 1 1 d . . .
H17A H 0.7010 0.3323 0.8895 0.125 Uiso 1 1 calc R . .
H17B H 0.6573 0.2819 0.8739 0.125 Uiso 1 1 calc R . .
H17C H 0.6872 0.2784 0.9068 0.125 Uiso 1 1 calc R . .
C18 C 0.4925(4) 0.3014(4) 0.88181(14) 0.091(2) Uani 1 1 d . . .
H18A H 0.4339 0.3129 0.8898 0.136 Uiso 1 1 calc R . .
H18B H 0.4933 0.2628 0.8803 0.136 Uiso 1 1 calc R . .
H18C H 0.5006 0.3169 0.8627 0.136 Uiso 1 1 calc R . .
N1 N 0.6250 0.1250 1.08206(10) 0.0324(12) Uani 1 2 d S . .
N2 N 0.6250 0.2066(2) 1.1250 0.0339(13) Uani 1 2 d SD . .
H2 H 0.6250 0.1691(5) 1.1250 0.051 Uiso 1 2 d SD . .
N3 N 0.5298(3) 0.37026(18) 0.98440(10) 0.0559(13) Uani 1 1 d D . .
H3 H 0.4677(14) 0.371(2) 0.9788(13) 0.084 Uiso 1 1 d D . .
N4 N 0.5518(3) 0.3476(2) 0.92249(10) 0.0577(12) Uani 1 1 d D . .
H4 H 0.4955 0.3573 0.9263 0.087 Uiso 0.50 1 calc PRD . .
F1 F 0.39765(17) 0.31972(11) 1.01284(7) 0.0634(10) Uani 1 1 d . . .
F2 F 0.43065(17) 0.25227(11) 1.05602(7) 0.0607(9) Uani 1 1 d . . .
F3 F 0.74477(18) 0.27477(15) 1.04217(7) 0.0807(12) Uani 1 1 d . . .
F4 F 0.71378(19) 0.34433(16) 1.00140(7) 0.0872(13) Uani 1 1 d . . .
F5 F 0.3750 0.3750 0.94343(13) 0.157(4) Uani 1 2 d S . .
C19 C 0.3963(11) 0.2283(5) 0.9481(3) 0.092(5) Uani 0.50 1 d P . .
H19 H 0.3918 0.2666 0.9431 0.110 Uiso 0.50 1 calc PR . .
Cl1 Cl 0.3193(4) 0.21705(19) 0.97079(11) 0.144(2) Uani 0.50 1 d P . .
Cl2 Cl 0.3791(4) 0.19261(19) 0.91531(9) 0.1260(17) Uani 0.50 1 d P . .
Cl3 Cl 0.5097(3) 0.21714(16) 0.95810(10) 0.1154(15) Uani 0.50 1 d P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.040(3) 0.046(3) 0.047(3) 0.011(2) -0.005(2) 0.001(2)
C2 0.023(2) 0.044(3) 0.047(3) -0.004(2) 0.003(2) 0.002(2)
C3 0.015(2) 0.049(3) 0.041(3) -0.002(2) 0.0029(19) -0.0049(19)
C4 0.017(2) 0.050(3) 0.039(3) 0.002(2) 0.003(2) -0.0010(19)
C5 0.021(2) 0.055(3) 0.034(3) 0.006(2) -0.003(2) -0.002(2)
C6 0.032(3) 0.042(3) 0.041(3) 0.001(2) -0.003(2) 0.000(2)
C7 0.017(2) 0.078(4) 0.049(3) 0.017(3) -0.002(2) 0.004(2)
C8 0.026(3) 0.089(4) 0.046(3) 0.024(3) 0.003(2) -0.001(3)
C9 0.035(3) 0.051(3) 0.035(3) 0.001(2) 0.002(2) 0.009(2)
C10 0.020(2) 0.049(3) 0.057(3) -0.001(3) -0.004(2) 0.004(2)
C11 0.021(2) 0.042(3) 0.047(3) 0.008(2) 0.005(2) -0.002(2)
C13 0.044(3) 0.066(3) 0.057(3) 0.015(3) -0.004(3) 0.004(3)
C14 0.029(3) 0.085(4) 0.048(3) 0.019(3) -0.006(3) -0.008(3)
C16 0.024(3) 0.103(5) 0.067(4) -0.001(4) 0.003(3) -0.007(3)
C17 0.040(3) 0.133(6) 0.078(4) -0.026(4) -0.001(3) 0.010(4)
C18 0.042(3) 0.160(7) 0.070(4) -0.004(4) -0.006(3) -0.011(4)
N1 0.020(3) 0.044(3) 0.034(3) 0.000 0.000 -0.002(2)
N2 0.024(3) 0.045(3) 0.033(3) 0.000 -0.001(2) 0.000
N3 0.032(2) 0.081(3) 0.055(3) 0.026(3) 0.004(2) 0.011(2)
N4 0.024(2) 0.097(3) 0.052(3) 0.003(3) 0.002(2) 0.002(2)
F1 0.0246(15) 0.0640(19) 0.102(2) 0.0304(17) -0.0038(15) 0.0056(13)
F2 0.0240(14) 0.0617(18) 0.096(2) 0.0309(17) 0.0002(15) -0.0025(13)
F3 0.0222(15) 0.146(3) 0.074(2) 0.062(2) 0.0004(14) 0.0025(17)
F4 0.0281(17) 0.157(3) 0.077(2) 0.068(2) 0.0042(16) -0.0003(18)
F5 0.064(4) 0.334(11) 0.073(4) 0.000 0.000 0.049(5)
C19 0.120(12) 0.078(9) 0.077(9) 0.022(7) 0.024(9) 0.036(8)
Cl1 0.179(5) 0.120(3) 0.132(4) 0.023(3) 0.061(4) 0.035(3)
Cl2 0.164(5) 0.111(3) 0.103(3) -0.013(3) -0.029(3) -0.022(3)
Cl3 0.131(4) 0.109(3) 0.106(3) 0.004(2) -0.037(3) 0.028(3)

_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 C1 1.348(9) 11_556 ?
C1 C2 1.441(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(6) . ?
C2 N2 1.388(6) . ?
C3 C4 1.408(6) . ?
C3 C6 1.492(6) . ?
C4 N1 1.363(5) . ?
C4 C5 1.449(6) . ?
C5 C5 1.324(9) 14_545 ?
C5 H5 0.9500 . ?
C6 C7 1.371(6) . ?
C6 C11 1.382(6) . ?
C7 F3 1.356(5) . ?
C7 C8 1.373(7) . ?
C8 F4 1.347(5) . ?
C8 C9 1.393(7) . ?
C9 N3 1.367(6) . ?
C9 C10 1.402(7) . ?
C10 F1 1.354(5) . ?
C10 C11 1.360(6) . ?
C11 F2 1.348(5) . ?
C13 N3 1.445(7) . ?
C13 C14 1.507(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N4 1.445(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 N4 1.258(7) . ?
C16 C18 1.496(8) . ?
C16 C17 1.501(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1 C4 1.363(5) 14_545 ?
N2 C2 1.388(6) 11_556 ?
N2 H2 0.949(10) . ?
N3 H3 0.95(3) . ?
N4 H4 0.8800 . ?
C19 Cl1 1.576(14) . ?
C19 Cl3 1.749(16) . ?
C19 Cl2 1.795(15) . ?
C19 H19 1.0000 . ?

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
C1 C1 C2 108.2(3) 11_556 . ?
C1 C1 H1 125.9 11_556 . ?
C2 C1 H1 125.9 . . ?
C3 C2 N2 124.5(4) . . ?
C3 C2 C1 127.7(4) . . ?
N2 C2 C1 107.7(4) . . ?
C2 C3 C4 125.9(4) . . ?
C2 C3 C6 117.1(4) . . ?
C4 C3 C6 117.0(4) . . ?
N1 C4 C3 125.7(4) . . ?
N1 C4 C5 110.1(4) . . ?
C3 C4 C5 124.2(4) . . ?
C5 C5 C4 107.0(3) 14_545 . ?
C5 C5 H5 126.5 14_545 . ?
C4 C5 H5 126.5 . . ?
C7 C6 C11 114.2(4) . . ?
C7 C6 C3 123.9(4) . . ?
C11 C6 C3 121.9(4) . . ?
F3 C7 C6 118.6(4) . . ?
F3 C7 C8 117.3(4) . . ?
C6 C7 C8 124.1(4) . . ?
F4 C8 C7 118.3(4) . . ?
F4 C8 C9 119.7(4) . . ?
C7 C8 C9 122.0(4) . . ?
N3 C9 C8 127.1(5) . . ?
N3 C9 C10 119.3(4) . . ?
C8 C9 C10 113.6(4) . . ?
F1 C10 C11 120.2(4) . . ?
F1 C10 C9 116.6(4) . . ?
C11 C10 C9 123.3(4) . . ?
F2 C11 C10 118.6(4) . . ?
F2 C11 C6 118.5(4) . . ?
C10 C11 C6 122.9(4) . . ?
N3 C13 C14 114.1(5) . . ?
N3 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
N3 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
N4 C14 C13 110.6(4) . . ?
N4 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N4 C16 C18 120.5(5) . . ?
N4 C16 C17 124.6(5) . . ?
C18 C16 C17 114.8(6) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 N1 C4 105.7(5) 14_545 . ?
C2 N2 C2 108.2(5) 11_556 . ?
C2 N2 H2 125.9(3) 11_556 . ?
C2 N2 H2 125.9(3) . . ?
C9 N3 C13 127.0(4) . . ?
C9 N3 H3 117(4) . . ?
C13 N3 H3 114(4) . . ?
C16 N4 C14 119.7(4) . . ?
C16 N4 H4 120.2 . . ?
C14 N4 H4 120.2 . . ?
Cl1 C19 Cl3 118.1(8) . . ?
Cl1 C19 Cl2 112.4(10) . . ?
Cl3 C19 Cl2 106.3(7) . . ?
Cl1 C19 H19 106.4 . . ?
Cl3 C19 H19 106.4 . . ?
Cl2 C19 H19 106.4 . . ?

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
C1 C1 C2 C3 -175.6(5) 11_556 . . . ?
C1 C1 C2 N2 2.1(6) 11_556 . . . ?
N2 C2 C3 C4 -5.8(6) . . . . ?
C1 C2 C3 C4 171.6(4) . . . . ?
N2 C2 C3 C6 176.0(3) . . . . ?
C1 C2 C3 C6 -6.7(6) . . . . ?
C2 C3 C4 N1 6.0(6) . . . . ?
C6 C3 C4 N1 -175.8(3) . . . . ?
C2 C3 C4 C5 -171.8(4) . . . . ?
C6 C3 C4 C5 6.4(6) . . . . ?
N1 C4 C5 C5 -2.7(6) . . . 14_545 ?
C3 C4 C5 C5 175.4(4) . . . 14_545 ?
C2 C3 C6 C7 90.4(6) . . . . ?
C4 C3 C6 C7 -88.0(6) . . . . ?
C2 C3 C6 C11 -92.0(5) . . . . ?
C4 C3 C6 C11 89.6(5) . . . . ?
C11 C6 C7 F3 -179.4(5) . . . . ?
C3 C6 C7 F3 -1.7(8) . . . . ?
C11 C6 C7 C8 0.2(8) . . . . ?
C3 C6 C7 C8 177.9(5) . . . . ?
F3 C7 C8 F4 -1.7(8) . . . . ?
C6 C7 C8 F4 178.6(5) . . . . ?
F3 C7 C8 C9 179.1(5) . . . . ?
C6 C7 C8 C9 -0.5(9) . . . . ?
F4 C8 C9 N3 0.3(9) . . . . ?
C7 C8 C9 N3 179.4(5) . . . . ?
F4 C8 C9 C10 -178.9(5) . . . . ?
C7 C8 C9 C10 0.2(8) . . . . ?
N3 C9 C10 F1 1.9(7) . . . . ?
C8 C9 C10 F1 -178.9(4) . . . . ?
N3 C9 C10 C11 -178.9(5) . . . . ?
C8 C9 C10 C11 0.4(7) . . . . ?
F1 C10 C11 F2 -2.8(7) . . . . ?
C9 C10 C11 F2 178.1(4) . . . . ?
F1 C10 C11 C6 178.5(4) . . . . ?
C9 C10 C11 C6 -0.7(8) . . . . ?
C7 C6 C11 F2 -178.4(4) . . . . ?
C3 C6 C11 F2 3.8(7) . . . . ?
C7 C6 C11 C10 0.4(7) . . . . ?
C3 C6 C11 C10 -177.4(4) . . . . ?
N3 C13 C14 N4 63.9(6) . . . . ?
C3 C4 N1 C4 -177.1(5) . . . 14_545 ?
C5 C4 N1 C4 1.0(2) . . . 14_545 ?
C3 C2 N2 C2 177.1(5) . . . 11_556 ?
C1 C2 N2 C2 -0.8(2) . . . 11_556 ?
C8 C9 N3 C13 5.9(9) . . . . ?
C10 C9 N3 C13 -175.0(5) . . . . ?
C14 C13 N3 C9 76.9(7) . . . . ?
C18 C16 N4 C14 179.6(6) . . . . ?
C17 C16 N4 C14 -1.5(9) . . . . ?
C13 C14 N4 C16 179.9(5) . . . . ?

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.125 0.875 0.125 148 48 ' '
2 -0.125 0.375 0.125 148 49 ' '
3 0.125 0.125 0.375 148 48 ' '
4 0.125 0.625 0.375 148 49 ' '
5 -0.125 0.375 0.625 148 48 ' '
6 -0.125 0.875 0.625 148 49 ' '
7 0.125 0.625 0.875 148 48 ' '
8 0.125 0.125 0.875 148 49 ' '
9 0.375 0.375 0.125 148 48 ' '
10 0.375 0.875 0.125 148 49 ' '
11 0.375 0.875 0.625 148 48 ' '
12 0.375 0.375 0.625 148 49 ' '
13 0.625 0.625 0.375 148 48 ' '
14 0.625 0.125 0.375 148 49 ' '
15 0.625 0.125 0.875 148 48 ' '
16 0.625 0.625 0.875 148 49 ' '
_platon_squeeze_details          
;
;

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 F5 0.95(3) 2.14(4) 2.972(6) 146(5) .
N4 H4 F5 0.88 1.99 2.856(5) 167.9 .

_diffrn_measured_fraction_theta_max 0.945
_diffrn_reflns_theta_full        25.32
_diffrn_measured_fraction_theta_full 0.945
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.072

# ===== END ===== #

_database_code_depnum_ccdc_archive 'CCDC 732151'