# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_exp_5151
_database_code_depnum_ccdc_archive 'CCDC 1836980'
_audit_update_record             
;
2018-04-13 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'pillar[6]pyridinium hexachloride salt hydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H36 Cl6 N6 O10'
_chemical_formula_weight         925.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   22.3483(4)
_cell_length_b                   22.3483(4)
_cell_length_c                   8.00310(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3461.61(13)
_cell_formula_units_Z            3
_cell_measurement_temperature    100.1(1)
_cell_measurement_reflns_used    11730
_cell_measurement_theta_min      3.952
_cell_measurement_theta_max      71.849

_exptl_crystal_description       'hollow prism'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             1428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    3.881
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.424
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.29
_diffrn_reflns_number            15744
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.983
_diffrn_reflns_theta_max         71.920
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1507
_reflns_number_gt                1499
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;The asymmetric unit comprises one sixth of the macrocycle, one chloride anion, water molecule disordered over
two positions O1W and O1WA (refined with 0.5 site occupancy factors), and another water molecule residing in the 
macrocyclic cavity, refined as disordered over O2W and O2WA positions (refined with 0.33333 site occupancy factors 
because of their close position to the three-fold rotoinversion crystallographic axes).The crystal structure is a 
peculiar example of the two types of the whole-molecule disorder. Firstly, the P[6]P macrocycle has two orientations 
on the same site in the different unit cells. Moreover, the nitrogen atoms of the pyridinium rings cannot be reliably 
distinguished from the carbon atoms, therefore, the additional disorder has been introduced into the model. This 
substitutional disorder implies that the same site may be occupied by different atoms (carbon or nitrogen) in the 
different unit cells. As neither position has clear advantage over another, it is equally possible that nitrogen atoms
might be found in the clockwise or anticlockwise directions around the macrocycle. The disorder model was built using
PART instructions. The soft similarity restraints SIMU and DELU on anisotropic displacement parameters of P[6]P atoms 
have been applied during the refinement. The positional substitutional disorder of nitrogen and carbon atoms 
sharing the same site have been built using EXYZ (same position) and EADP (same thermal parameters) constraints.
All components of the structure except one chloride anion are disordered.,whole-molecule disorder
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+11.1606P] 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         1507
_refine_ls_number_parameters     172
_refine_ls_number_restraints     98
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.004
_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_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
C5 C 0.2509(12) 0.0646(10) 0.0235(14) 0.018(2) Uani 0.25 1 d . U P A 1
C2 C 0.1866(8) -0.0642(9) 0.0205(14) 0.0152(19) Uani 0.25 1 d . U P A 1
C1 C 0.1565(9) -0.0829(11) -0.134(3) 0.020(2) Uani 0.5 1 d . U P A 1
H1 H 0.1780 -0.0547 -0.2291 0.024 Uiso 0.5 1 calc R U P A 1
C4 C 0.1532(6) -0.1090(7) 0.1560(18) 0.0185(18) Uani 0.5 1 d . U P A 1
H4 H 0.1731 -0.0970 0.2643 0.022 Uiso 0.5 1 calc R U P A 1
C7 C 0.2551(2) 0.0006(2) 0.0475(7) 0.0176(8) Uani 0.5 1 d . U P A 1
H7A H 0.2715 0.0002 0.1623 0.021 Uiso 0.5 1 calc R U P A 1
H7B H 0.2894 0.0010 -0.0316 0.021 Uiso 0.5 1 calc R U P A 1
C6 C 0.2380(14) 0.0957(9) 0.149(3) 0.022(2) Uani 0.5 1 d . U P A 1
H6 H 0.2271 0.0737 0.2549 0.026 Uiso 0.5 1 calc R U P A 1
C3 C 0.2623(9) 0.0923(6) -0.1333(17) 0.0169(17) Uani 0.5 1 d . U P A 1
H3 H 0.2700 0.0699 -0.2247 0.020 Uiso 0.5 1 calc R U P A 1
N2 N 0.1866(8) -0.0642(9) 0.0205(14) 0.0152(19) Uani 0.25 1 d . . P B 2
N5 N 0.2509(12) 0.0646(10) 0.0235(14) 0.018(2) Uani 0.25 1 d . . P C 2
C5A C 0.2507(11) 0.0646(9) -0.0197(14) 0.0153(19) Uani 0.25 1 d . U P D 3
C2A C 0.1856(9) -0.0654(9) -0.0242(13) 0.015(2) Uani 0.25 1 d . U P D 3
C1A C 0.1429(9) -0.0951(11) -0.152(2) 0.020(2) Uani 0.5 1 d . U P D 3
H1A H 0.1549 -0.0726 -0.2578 0.024 Uiso 0.5 1 calc R U P D 3
C4A C 0.1698(6) -0.0931(7) 0.1328(17) 0.0164(17) Uani 0.5 1 d . U P D 3
H4A H 0.2001 -0.0708 0.2241 0.020 Uiso 0.5 1 calc R U P D 3
C7A C 0.2545(2) -0.0007(2) -0.0477(7) 0.0168(8) Uani 0.5 1 d . U P D 3
H7A1 H 0.2713 -0.0001 -0.1624 0.020 Uiso 0.5 1 calc R U P D 3
H7A2 H 0.2882 -0.0013 0.0314 0.020 Uiso 0.5 1 calc R U P D 3
C6A C 0.2391(13) 0.0823(9) 0.139(3) 0.0184(18) Uani 0.5 1 d . U P D 3
H6A H 0.2323 0.0538 0.2331 0.022 Uiso 0.5 1 calc R U P D 3
C3A C 0.2629(8) 0.1095(6) -0.1546(16) 0.0167(18) Uani 0.5 1 d . U P D 3
H3A H 0.2712 0.0975 -0.2626 0.020 Uiso 0.5 1 calc R U P D 3
N5A N 0.2507(11) 0.0646(9) -0.0197(14) 0.0153(19) Uani 0.25 1 d . . P E 4
N2A N 0.1856(9) -0.0654(9) -0.0242(13) 0.015(2) Uani 0.25 1 d . . P F 4
O1W O 0.3225(3) 0.5503(2) 0.2360(7) 0.0620(12) Uani 0.5 1 d . . P G 1
O1WA O 0.3442(3) 0.5612(3) 0.0971(7) 0.0620(12) Uani 0.5 1 d . . P H 2
O2W O 0.3080(11) 0.5738(7) 0.5794(19) 0.118(8) Uani 0.3333 1 d . . P I 1
O2WA O 0.2661(8) 0.5742(7) 0.5790(19) 0.116(7) Uani 0.3333 1 d . . P J 2
Cl1 Cl 0.33327(2) 0.41816(2) 0.16667(5) 0.01868(19) 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
C5 C6 1.331(14) . ?
C5 C3 1.365(10) . ?
C5 C7 1.493(18) . ?
C2 C1 1.371(12) . ?
C2 C4 1.410(12) . ?
C2 C7 1.506(15) . ?
C1 C6 1.348(17) 11 ?
C4 C3 1.374(12) 11 ?
C6 C1 1.348(17) 12 ?
C3 C4 1.374(12) 12 ?
C5A C6A 1.391(15) . ?
C5A C3A 1.404(12) . ?
C5A C7A 1.520(17) . ?
C2A C1A 1.330(11) . ?
C2A C4A 1.367(10) . ?
C2A C7A 1.506(15) . ?
C1A C6A 1.371(17) 11 ?
C4A C3A 1.360(11) 11 ?
C6A C1A 1.371(17) 12 ?
C3A C4A 1.360(11) 12 ?

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 C5 C3 119.7(18) . . ?
C6 C5 C7 122.5(12) . . ?
C3 C5 C7 117.8(11) . . ?
C1 C2 C4 118.2(14) . . ?
C1 C2 C7 122.1(11) . . ?
C4 C2 C7 119.7(8) . . ?
C6 C1 C2 118.5(19) 11 . ?
C3 C4 C2 120.8(13) 11 . ?
C5 C7 C2 112.4(12) . . ?
C5 C6 C1 124(2) . 12 ?
C5 C3 C4 118.6(15) . 12 ?
C6A C5A C3A 119.7(16) . . ?
C6A C5A C7A 121.0(12) . . ?
C3A C5A C7A 119.2(9) . . ?
C1A C2A C4A 121.6(15) . . ?
C1A C2A C7A 121.1(10) . . ?
C4A C2A C7A 117.2(9) . . ?
C2A C1A C6A 123(2) . 11 ?
C3A C4A C2A 118.1(13) 11 . ?
C2A C7A C5A 112.5(11) . . ?
C1A C6A C5A 117(2) 12 . ?
C4A C3A C5A 120.9(13) 12 . ?

_refine_diff_density_max         0.888
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 'Vapour deposition'
