# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2024

####################################################################### 
# 
# 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 
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data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1050752'
_audit_update_record             
;
2015-02-21 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            
Naphthalenediimide-bis-methoxyphenylphosphonium
_chemical_formula_moiety         'C68 H70 N2 O10 P2, 2(B F4)'
_chemical_formula_sum            'C68 H70 B2 F8 N2 O10 P2'
_chemical_formula_weight         1310.82

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2080(8)
_cell_length_b                   12.3079(5)
_cell_length_c                   13.6327(11)
_cell_angle_alpha                92.111(5)
_cell_angle_beta                 94.947(7)
_cell_angle_gamma                92.151(5)
_cell_volume                     1703.8(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    14110
_cell_measurement_theta_min      2
_cell_measurement_theta_max      29

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.143
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction 
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15341
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.902
_diffrn_reflns_theta_max         29.302
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7902
_reflns_number_gt                4725
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-92(Altomare et. al.,1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
Refinement showed a highly disordered BF4 group and also there was
disorder in the terminal methyl and methylene groups of the hexyl
chain. The disorder in the methyl(C13) and methylene(C12) group was
 resolvedby splittng these atoms into two positions
 and refining their sofsand Uiso as free variables over fixed C-C 
distances. Two hydrogens attached to the adjacent methylene C11 were
also split over two positions so as to correctly define the tetrahdral
disposition around it. 
 The disorder in the BF4 was also resolved in similar manner
 by splitting all five atoms 
with SADI restraints over B-F bonding and F-F non-bondings
 distances. Similar ADP(SIMU) and rigid bond (DELU) restraints
had to be used for the B atom which tend to be NPD on anisotropic
refinement.  
Apart from that there was some very diffused electron density of
a maxima around 1.4 eA3 which 
could not be modelled, but could be some solvent molecule. Therefore
it was SQEEZED out using the PLATON routine. The subsequent  model
refined well with much improved R value. It also showed SAV of the 
100 A3 which matches well with the volume of the void created (99 A3)
on removing the solvent. The number of electron recovered (16)from
the site indicate that it could be  a methanol molecule or 1.5
water molecules in the asymmetric unit.
 
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     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7902
_refine_ls_number_parameters     441
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0873
_refine_ls_wR_factor_ref         0.3127
_refine_ls_wR_factor_gt          0.2728
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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
C1 C 0.3557(3) 0.4668(2) 0.4083(2) 0.0383(7) Uani 1 1 d . . . . .
C2 C 0.4062(3) 0.3859(2) 0.3490(2) 0.0388(6) Uani 1 1 d . . . . .
C3 C 0.4628(3) 0.6433(3) 0.6286(2) 0.0422(7) Uani 1 1 d . . . . .
H3 H 0.4283 0.6968 0.6677 0.051 Uiso 1 1 calc R U . . .
C4 C 0.3841(3) 0.5948(2) 0.5507(2) 0.0391(7) Uani 1 1 d . . . . .
C5 C 0.4348(3) 0.5156(2) 0.4889(2) 0.0367(6) Uani 1 1 d . . . . .
C6 C 0.2195(3) 0.5027(3) 0.3875(2) 0.0415(7) Uani 1 1 d . . . . .
C7 C 0.2481(3) 0.6285(3) 0.5330(2) 0.0466(8) Uani 1 1 d . . . . .
C8 C 0.0391(3) 0.6214(3) 0.4275(3) 0.0558(9) Uani 1 1 d . . . . .
H8A H -0.0032 0.6279 0.4883 0.067 Uiso 1 1 calc R U . . .
H8B H -0.0114 0.5675 0.3846 0.067 Uiso 1 1 calc R U . . .
C9 C 0.0372(5) 0.7298(4) 0.3786(3) 0.0818(14) Uani 1 1 d . . . . .
H9A H -0.0529 0.7529 0.3721 0.098 Uiso 1 1 calc R U . . .
H9B H 0.0881 0.7830 0.4220 0.098 Uiso 1 1 calc R U . . .
C10 C 0.0889(6) 0.7321(4) 0.2799(4) 0.0980(16) Uani 1 1 d . . . . .
H10A H 0.0401 0.6780 0.2362 0.118 Uiso 1 1 calc R U . . .
H10B H 0.1804 0.7125 0.2861 0.118 Uiso 1 1 calc R U . . .
C11 C 0.0794(9) 0.8417(6) 0.2344(5) 0.142(3) Uani 1 1 d D . . . .
H11A H 0.1416 0.8933 0.2705 0.171 Uiso 0.33(17) 1 calc R U P A 1
H11B H -0.0084 0.8680 0.2391 0.171 Uiso 0.33(17) 1 calc R U P A 1
H11C H 0.1062 0.8961 0.2863 0.171 Uiso 0.67(17) 1 calc R U P A 2
H11D H -0.0131 0.8516 0.2155 0.171 Uiso 0.67(17) 1 calc R U P A 2
C12 C 0.109(3) 0.8339(18) 0.1260(11) 0.156(8) Uani 0.519(9) 1 d D . P B 1
H12A H 0.2023 0.8257 0.1228 0.187 Uiso 0.519(9) 1 calc R U P B 1
H12B H 0.0633 0.7693 0.0948 0.187 Uiso 0.519(9) 1 calc R U P B 1
C12' C 0.154(3) 0.870(2) 0.1461(13) 0.156(8) Uani 0.481(9) 1 d D . P B 2
H12C H 0.1623 0.9477 0.1390 0.187 Uiso 0.481(9) 1 calc R U P B 2
H12D H 0.2412 0.8401 0.1512 0.187 Uiso 0.481(9) 1 calc R U P B 2
C13 C 0.0673(15) 0.9318(11) 0.0690(9) 0.126(3) Uani 0.519(9) 1 d D . P B 1
H13A H 0.1204 0.9396 0.0147 0.189 Uiso 0.519(9) 1 calc R U P B 1
H13B H 0.0788 0.9960 0.1116 0.189 Uiso 0.519(9) 1 calc R U P B 1
H13C H -0.0236 0.9221 0.0445 0.189 Uiso 0.519(9) 1 calc R U P B 1
C13' C 0.0681(16) 0.8156(13) 0.0630(12) 0.126(3) Uani 0.481(9) 1 d D . P B 2
H13D H 0.1195 0.8002 0.0088 0.189 Uiso 0.481(9) 1 calc R U P B 2
H13E H -0.0008 0.8630 0.0424 0.189 Uiso 0.481(9) 1 calc R U P B 2
H13F H 0.0300 0.7490 0.0843 0.189 Uiso 0.481(9) 1 calc R U P B 2
C14 C 0.1789(3) 0.2385(3) 0.2890(2) 0.0428(7) Uani 1 1 d . . . . .
C15 C 0.1971(4) 0.1945(3) 0.3820(3) 0.0554(9) Uani 1 1 d . . . . .
H15 H 0.2758 0.2082 0.4209 0.066 Uiso 1 1 calc R U . . .
C16 C 0.0978(4) 0.1307(3) 0.4158(3) 0.0605(10) Uani 1 1 d . . . . .
H16 H 0.1109 0.1002 0.4771 0.073 Uiso 1 1 calc R U . . .
C17 C -0.0195(4) 0.1116(3) 0.3606(3) 0.0522(8) Uani 1 1 d . . . . .
C18 C -0.0399(3) 0.1557(3) 0.2696(3) 0.0555(9) Uani 1 1 d . . . . .
H18 H -0.1199 0.1430 0.2322 0.067 Uiso 1 1 calc R U . . .
C19 C 0.0581(4) 0.2187(3) 0.2342(2) 0.0530(8) Uani 1 1 d . . . . .
H19 H 0.0437 0.2486 0.1727 0.064 Uiso 1 1 calc R U . . .
C20 C -0.2366(5) 0.0315(4) 0.3514(4) 0.0939(16) Uani 1 1 d . . . . .
H20A H -0.2904 -0.0132 0.3895 0.141 Uiso 1 1 calc R U . . .
H20B H -0.2281 -0.0046 0.2887 0.141 Uiso 1 1 calc R U . . .
H20C H -0.2769 0.0999 0.3412 0.141 Uiso 1 1 calc R U . . .
C21 C 0.2777(3) 0.3995(2) 0.1447(2) 0.0435(7) Uani 1 1 d . . . . .
C22 C 0.2177(4) 0.3550(3) 0.0556(2) 0.0554(9) Uani 1 1 d . . . . .
H22 H 0.1936 0.2812 0.0507 0.067 Uiso 1 1 calc R U . . .
C24 C 0.1935(4) 0.4170(3) -0.0248(3) 0.0611(10) Uani 1 1 d . . . . .
H24 H 0.1501 0.3864 -0.0826 0.073 Uiso 1 1 calc R U . . .
C25 C 0.2346(4) 0.5268(3) -0.0192(3) 0.0589(9) Uani 1 1 d . . . . .
C26 C 0.2984(5) 0.5710(3) 0.0673(3) 0.0704(12) Uani 1 1 d . . . . .
H26 H 0.3273 0.6437 0.0708 0.084 Uiso 1 1 calc R U . . .
C27 C 0.3197(4) 0.5082(3) 0.1490(3) 0.0620(10) Uani 1 1 d . . . . .
H27 H 0.3624 0.5390 0.2070 0.074 Uiso 1 1 calc R U . . .
C28 C 0.1568(7) 0.5537(4) -0.1871(3) 0.0985(17) Uani 1 1 d . . . . .
H28A H 0.1523 0.6110 -0.2330 0.148 Uiso 1 1 calc R U . . .
H28B H 0.0695 0.5257 -0.1790 0.148 Uiso 1 1 calc R U . . .
H28C H 0.2078 0.4964 -0.2117 0.148 Uiso 1 1 calc R U . . .
C29 C 0.4202(3) 0.2142(3) 0.1980(2) 0.0446(7) Uani 1 1 d . . . . .
C30 C 0.5230(4) 0.2499(3) 0.1429(3) 0.0547(9) Uani 1 1 d . . . . .
H30 H 0.5342 0.3234 0.1310 0.066 Uiso 1 1 calc R U . . .
C31 C 0.6066(4) 0.1764(3) 0.1068(3) 0.0638(10) Uani 1 1 d . . . . .
H31 H 0.6756 0.2006 0.0719 0.077 Uiso 1 1 calc R U . . .
C32 C 0.5888(4) 0.0668(3) 0.1220(3) 0.0618(10) Uani 1 1 d . . . . .
C33 C 0.4870(4) 0.0297(3) 0.1759(3) 0.0625(10) Uani 1 1 d . . . . .
H33 H 0.4748 -0.0441 0.1865 0.075 Uiso 1 1 calc R U . . .
C34 C 0.4050(4) 0.1044(3) 0.2129(3) 0.0537(8) Uani 1 1 d . . . . .
H34 H 0.3374 0.0800 0.2491 0.064 Uiso 1 1 calc R U . . .
C35 C 0.6610(6) -0.1139(4) 0.0938(4) 0.107(2) Uani 1 1 d . . . . .
H35A H 0.7295 -0.1501 0.0632 0.160 Uiso 1 1 calc R U . . .
H35B H 0.5770 -0.1389 0.0622 0.160 Uiso 1 1 calc R U . . .
H35C H 0.6653 -0.1300 0.1623 0.160 Uiso 1 1 calc R U . . .
O1 O 0.1496(2) 0.46407(19) 0.31667(16) 0.0526(6) Uani 1 1 d . . . . .
O2 O 0.1993(3) 0.6922(2) 0.58748(19) 0.0683(8) Uani 1 1 d . . . . .
O3 O -0.1111(3) 0.0498(2) 0.4021(2) 0.0746(8) Uani 1 1 d . . . . .
O4 O 0.2174(4) 0.5953(2) -0.0942(2) 0.0836(10) Uani 1 1 d . . . . .
O5 O 0.6777(3) 0.0024(3) 0.0841(2) 0.0892(10) Uani 1 1 d . . . . .
P1 P 0.31334(8) 0.31295(6) 0.24506(5) 0.0403(3) Uani 1 1 d . . . . .
N1 N 0.1743(2) 0.5828(2) 0.44974(19) 0.0448(6) Uani 1 1 d . . . . .
B1 B 0.645(2) 0.6919(16) 0.3298(13) 0.452(15) Uani 0.617(5) 1 d D U P C 1
F1 F 0.6130(18) 0.7399(13) 0.4058(10) 0.300(7) Uani 0.617(5) 1 d D . P C 1
F2 F 0.7233(13) 0.6218(9) 0.3807(9) 0.245(5) Uani 0.617(5) 1 d D . P C 1
F3 F 0.7212(11) 0.7235(10) 0.2620(9) 0.230(5) Uani 0.617(5) 1 d D . P C 1
F4 F 0.5722(12) 0.6100(7) 0.2983(7) 0.189(4) Uani 0.617(5) 1 d D . P C 1
B1' B 0.580(2) 0.697(2) 0.3220(19) 0.452(15) Uani 0.383(5) 1 d D U P C 2
F1' F 0.503(2) 0.7504(17) 0.2484(14) 0.300(7) Uani 0.383(5) 1 d D . P C 2
F2' F 0.651(2) 0.7897(16) 0.3323(15) 0.245(5) Uani 0.383(5) 1 d D . P C 2
F3' F 0.6260(19) 0.6422(16) 0.2452(15) 0.230(5) Uani 0.383(5) 1 d D . P C 2
F4' F 0.4569(15) 0.6813(12) 0.3361(11) 0.189(4) Uani 0.383(5) 1 d D . P C 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
C1 C2 1.400(4) . ?
C1 C5 1.407(4) . ?
C1 C6 1.482(4) . ?
C2 C3 1.408(4) 2_666 ?
C2 P1 1.823(3) . ?
C3 C4 1.378(4) . ?
C3 C2 1.408(4) 2_666 ?
C3 H3 0.9300 . ?
C4 C5 1.407(4) . ?
C4 C7 1.467(4) . ?
C5 C5 1.411(6) 2_666 ?
C6 O1 1.220(4) . ?
C6 N1 1.395(4) . ?
C7 O2 1.210(4) . ?
C7 N1 1.396(4) . ?
C8 N1 1.486(4) . ?
C8 C9 1.514(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.488(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.508(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12' 1.523(18) . ?
C11 C12 1.534(16) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C12 C13 1.512(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12' C13' 1.493(18) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?
C14 C19 1.394(5) . ?
C14 C15 1.397(5) . ?
C14 P1 1.781(3) . ?
C15 C16 1.380(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(5) . ?
C16 H16 0.9300 . ?
C17 O3 1.358(4) . ?
C17 C18 1.375(5) . ?
C18 C19 1.374(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O3 1.409(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C27 1.387(5) . ?
C21 C22 1.396(4) . ?
C21 P1 1.786(3) . ?
C22 C24 1.369(5) . ?
C22 H22 0.9300 . ?
C24 C25 1.397(5) . ?
C24 H24 0.9300 . ?
C25 O4 1.352(4) . ?
C25 C26 1.380(5) . ?
C26 C27 1.387(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 O4 1.430(5) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C34 1.379(5) . ?
C29 C30 1.408(5) . ?
C29 P1 1.801(3) . ?
C30 C31 1.374(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.379(6) . ?
C31 H31 0.9300 . ?
C32 O5 1.350(4) . ?
C32 C33 1.395(6) . ?
C33 C34 1.378(5) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 O5 1.448(6) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
B1 F1 1.248(16) . ?
B1 F4 1.268(17) . ?
B1 F3 1.319(16) . ?
B1 F2 1.366(18) . ?
B1' F4' 1.293(18) . ?
B1' F2' 1.323(18) . ?
B1' F3' 1.356(19) . ?
B1' F1' 1.410(19) . ?
F1' F4' 1.59(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
C2 C1 C5 120.0(3) . . ?
C2 C1 C6 121.0(3) . . ?
C5 C1 C6 119.0(3) . . ?
C1 C2 C3 118.4(3) . 2_666 ?
C1 C2 P1 124.6(2) . . ?
C3 C2 P1 117.0(2) 2_666 . ?
C4 C3 C2 122.0(3) . 2_666 ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 2_666 . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 C7 118.7(3) . . ?
C5 C4 C7 121.1(3) . . ?
C4 C5 C1 120.6(3) . . ?
C4 C5 C5 118.5(3) . 2_666 ?
C1 C5 C5 120.9(3) . 2_666 ?
O1 C6 N1 121.0(3) . . ?
O1 C6 C1 120.6(3) . . ?
N1 C6 C1 118.4(3) . . ?
O2 C7 N1 120.2(3) . . ?
O2 C7 C4 122.8(3) . . ?
N1 C7 C4 117.0(3) . . ?
N1 C8 C9 113.0(3) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 116.1(4) . . ?
C10 C9 H9A 108.3 . . ?
C8 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
C8 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C9 C10 C11 113.0(5) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12' 121.4(13) . . ?
C10 C11 C12 110.7(9) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C10 C11 H11C 107.0 . . ?
C12' C11 H11C 107.0 . . ?
C10 C11 H11D 107.0 . . ?
C12' C11 H11D 107.0 . . ?
H11C C11 H11D 106.7 . . ?
C13 C12 C11 113.4(15) . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C13' C12' C11 101.7(15) . . ?
C13' C12' H12C 111.4 . . ?
C11 C12' H12C 111.4 . . ?
C13' C12' H12D 111.4 . . ?
C11 C12' H12D 111.4 . . ?
H12C C12' H12D 109.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12' C13' H13D 109.5 . . ?
C12' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C12' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C19 C14 C15 118.4(3) . . ?
C19 C14 P1 123.4(2) . . ?
C15 C14 P1 118.2(3) . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
O3 C17 C16 115.9(3) . . ?
O3 C17 C18 124.0(3) . . ?
C16 C17 C18 120.1(3) . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C14 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C27 C21 C22 118.3(3) . . ?
C27 C21 P1 121.8(3) . . ?
C22 C21 P1 119.5(2) . . ?
C24 C22 C21 121.7(3) . . ?
C24 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C24 C25 119.4(3) . . ?
C22 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
O4 C25 C26 116.0(3) . . ?
O4 C25 C24 124.5(3) . . ?
C26 C25 C24 119.5(3) . . ?
C25 C26 C27 120.7(4) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C21 C27 C26 120.3(3) . . ?
C21 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
O4 C28 H28A 109.5 . . ?
O4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C34 C29 C30 118.4(3) . . ?
C34 C29 P1 122.7(3) . . ?
C30 C29 P1 118.9(3) . . ?
C31 C30 C29 120.1(3) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 120.4(4) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
O5 C32 C31 115.2(4) . . ?
O5 C32 C33 124.5(4) . . ?
C31 C32 C33 120.3(3) . . ?
C34 C33 C32 118.7(4) . . ?
C34 C33 H33 120.6 . . ?
C32 C33 H33 120.6 . . ?
C33 C34 C29 122.0(4) . . ?
C33 C34 H34 119.0 . . ?
C29 C34 H34 119.0 . . ?
O5 C35 H35A 109.5 . . ?
O5 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O5 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C17 O3 C20 118.9(3) . . ?
C25 O4 C28 118.9(3) . . ?
C32 O5 C35 117.9(4) . . ?
C14 P1 C21 117.48(15) . . ?
C14 P1 C29 106.68(15) . . ?
C21 P1 C29 104.43(14) . . ?
C14 P1 C2 108.86(14) . . ?
C21 P1 C2 111.76(14) . . ?
C29 P1 C2 106.93(14) . . ?
C6 N1 C7 123.8(2) . . ?
C6 N1 C8 118.6(3) . . ?
C7 N1 C8 117.6(3) . . ?
F1 B1 F4 116.0(17) . . ?
F1 B1 F3 131.2(18) . . ?
F4 B1 F3 110.7(15) . . ?
F1 B1 F2 93.8(13) . . ?
F4 B1 F2 87.7(14) . . ?
F3 B1 F2 101.6(15) . . ?
F4' B1' F2' 128(2) . . ?
F4' B1' F3' 117.6(19) . . ?
F2' B1' F3' 105.1(19) . . ?
F4' B1' F1' 71.8(14) . . ?
F2' B1' F1' 85.1(17) . . ?
F3' B1' F1' 84.6(16) . . ?
B1' F1' F4' 50.7(9) . . ?
B1' F4' F1' 57.5(11) . . ?

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
C5 C1 C2 C3 -0.9(4) . . . 2_666 ?
C6 C1 C2 C3 178.8(3) . . . 2_666 ?
C5 C1 C2 P1 178.0(2) . . . . ?
C6 C1 C2 P1 -2.3(4) . . . . ?
C2 C3 C4 C5 -1.7(5) 2_666 . . . ?
C2 C3 C4 C7 179.1(3) 2_666 . . . ?
C3 C4 C5 C1 -179.2(3) . . . . ?
C7 C4 C5 C1 0.0(5) . . . . ?
C3 C4 C5 C5 2.5(5) . . . 2_666 ?
C7 C4 C5 C5 -178.3(3) . . . 2_666 ?
C2 C1 C5 C4 -178.2(3) . . . . ?
C6 C1 C5 C4 2.1(4) . . . . ?
C2 C1 C5 C5 0.0(5) . . . 2_666 ?
C6 C1 C5 C5 -179.7(3) . . . 2_666 ?
C2 C1 C6 O1 -1.7(5) . . . . ?
C5 C1 C6 O1 178.0(3) . . . . ?
C2 C1 C6 N1 179.4(3) . . . . ?
C5 C1 C6 N1 -0.9(4) . . . . ?
C3 C4 C7 O2 -4.6(5) . . . . ?
C5 C4 C7 O2 176.2(3) . . . . ?
C3 C4 C7 N1 175.9(3) . . . . ?
C5 C4 C7 N1 -3.3(5) . . . . ?
N1 C8 C9 C10 63.4(5) . . . . ?
C8 C9 C10 C11 178.0(5) . . . . ?
C9 C10 C11 C12' 165.6(12) . . . . ?
C9 C10 C11 C12 -169.1(14) . . . . ?
C10 C11 C12 C13 165.1(15) . . . . ?
C12' C11 C12 C13 -74(4) . . . . ?
C10 C11 C12' C13' 80(2) . . . . ?
C12 C11 C12' C13' 9(3) . . . . ?
C19 C14 C15 C16 1.9(5) . . . . ?
P1 C14 C15 C16 -176.0(3) . . . . ?
C14 C15 C16 C17 -1.4(6) . . . . ?
C15 C16 C17 O3 -178.5(3) . . . . ?
C15 C16 C17 C18 0.3(6) . . . . ?
O3 C17 C18 C19 179.0(3) . . . . ?
C16 C17 C18 C19 0.3(6) . . . . ?
C17 C18 C19 C14 0.2(6) . . . . ?
C15 C14 C19 C18 -1.3(5) . . . . ?
P1 C14 C19 C18 176.4(3) . . . . ?
C27 C21 C22 C24 -3.6(6) . . . . ?
P1 C21 C22 C24 -177.2(3) . . . . ?
C21 C22 C24 C25 2.7(6) . . . . ?
C22 C24 C25 O4 179.1(4) . . . . ?
C22 C24 C25 C26 -0.3(6) . . . . ?
O4 C25 C26 C27 179.3(4) . . . . ?
C24 C25 C26 C27 -1.2(7) . . . . ?
C22 C21 C27 C26 2.0(6) . . . . ?
P1 C21 C27 C26 175.5(3) . . . . ?
C25 C26 C27 C21 0.4(7) . . . . ?
C34 C29 C30 C31 -1.1(5) . . . . ?
P1 C29 C30 C31 179.5(3) . . . . ?
C29 C30 C31 C32 1.6(6) . . . . ?
C30 C31 C32 O5 -179.4(3) . . . . ?
C30 C31 C32 C33 -1.2(6) . . . . ?
O5 C32 C33 C34 178.2(4) . . . . ?
C31 C32 C33 C34 0.2(6) . . . . ?
C32 C33 C34 C29 0.3(6) . . . . ?
C30 C29 C34 C33 0.1(5) . . . . ?
P1 C29 C34 C33 179.5(3) . . . . ?
C16 C17 O3 C20 176.8(4) . . . . ?
C18 C17 O3 C20 -2.0(6) . . . . ?
C26 C25 O4 C28 177.5(4) . . . . ?
C24 C25 O4 C28 -1.9(7) . . . . ?
C31 C32 O5 C35 -177.3(4) . . . . ?
C33 C32 O5 C35 4.5(6) . . . . ?
C19 C14 P1 C21 19.3(3) . . . . ?
C15 C14 P1 C21 -162.9(3) . . . . ?
C19 C14 P1 C29 -97.3(3) . . . . ?
C15 C14 P1 C29 80.4(3) . . . . ?
C19 C14 P1 C2 147.6(3) . . . . ?
C15 C14 P1 C2 -34.7(3) . . . . ?
C27 C21 P1 C14 127.6(3) . . . . ?
C22 C21 P1 C14 -59.0(3) . . . . ?
C27 C21 P1 C29 -114.5(3) . . . . ?
C22 C21 P1 C29 58.9(3) . . . . ?
C27 C21 P1 C2 0.8(4) . . . . ?
C22 C21 P1 C2 174.2(3) . . . . ?
C34 C29 P1 C14 -10.4(3) . . . . ?
C30 C29 P1 C14 169.0(3) . . . . ?
C34 C29 P1 C21 -135.4(3) . . . . ?
C30 C29 P1 C21 44.0(3) . . . . ?
C34 C29 P1 C2 106.0(3) . . . . ?
C30 C29 P1 C2 -74.6(3) . . . . ?
C1 C2 P1 C14 -62.4(3) . . . . ?
C3 C2 P1 C14 116.5(2) 2_666 . . . ?
C1 C2 P1 C21 69.0(3) . . . . ?
C3 C2 P1 C21 -112.1(2) 2_666 . . . ?
C1 C2 P1 C29 -177.3(3) . . . . ?
C3 C2 P1 C29 1.6(3) 2_666 . . . ?
O1 C6 N1 C7 178.5(3) . . . . ?
C1 C6 N1 C7 -2.6(5) . . . . ?
O1 C6 N1 C8 -0.6(5) . . . . ?
C1 C6 N1 C8 178.3(3) . . . . ?
O2 C7 N1 C6 -174.9(3) . . . . ?
C4 C7 N1 C6 4.6(5) . . . . ?
O2 C7 N1 C8 4.3(5) . . . . ?
C4 C7 N1 C8 -176.3(3) . . . . ?
C9 C8 N1 C6 -101.7(4) . . . . ?
C9 C8 N1 C7 79.1(4) . . . . ?
F2' B1' F1' F4' -133(2) . . . . ?
F3' B1' F1' F4' 121.4(18) . . . . ?
F2' B1' F4' F1' 68(2) . . . . ?
F3' B1' F4' F1' -74(2) . . . . ?

_refine_diff_density_max         0.989
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4
# 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 0.500 1.000 0.500 99 16 ' '
_platon_squeeze_details          
;
The sixteen electron recovered could be due to a methanol or 1.5 water
molecules. The volume of the void created matches well with the SAV of
99 A3 shown by PLATON.
;



