#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:55:48 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178967 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/96/4119652.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4119652
loop_
_publ_author_name
'Han-Yuan Gong'
'Brett M. Rambo'
'Vincent M. Lynch'
'Karin M. Keller'
'Jonathan L. Sessler'
_publ_contact_author_address
;
Department of Chemistry & Biochemistry, 
1 University Station A5300,
University of Texas at Austin, Austin, Texas, 78712-0165, USA;
College of Chemistry, Beijing Normal University, Beijing, 100875 (P. R. China); 
Department of Chemistry, Yonsei University, Seoul, 120-749, Korea;
;
_publ_contact_author_email
;
hyg2070@iccas.ac.cn; sessler@mail.utexas.edu
;
_publ_contact_author_name
;
Han-Yuan Gong and Jonathan L. Sessler
;
_publ_section_title
;
 "Texas-Sized" Molecular Boxes: Building Blocks for the Construction of
 Anion-Induced Supramolecular Species via Self-Assembly
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6330
_journal_page_last               6337
_journal_paper_doi               10.1021/ja401893w
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C36 H32 F24 N12 P4'
_chemical_formula_weight         1212.62
_chemical_name_common
;
cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](2,6-dimethylenepyridinyl)
_ 4PF6
;
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.889(5)
_cell_angle_beta                 101.014(5)
_cell_angle_gamma                112.004(5)
_cell_formula_units_Z            1
_cell_length_a                   8.563(5)
_cell_length_b                   10.026(5)
_cell_length_c                   15.094(5)
_cell_measurement_reflns_used    4018
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.13
_cell_volume                     1152.9(10)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device
;
Mercury2 (2x2 bin mode)
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_av_sigmaI/netI    0.1168
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9917
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6053
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.1705
_refine_ls_R_factor_gt           0.0840
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0250P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.2079
_reflns_number_gt                2044
_reflns_number_total             4018
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja401893w_si_006.cif
_cod_data_source_block           macrocycle4b
_cod_database_code               4119652
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
P1 P 0.2280(3) -0.0097(2) 0.68223(14) 0.0542(6) Uani 1 1 d .
P2 P 0.2096(3) 0.5336(2) 0.84616(14) 0.0544(6) Uani 1 1 d .
F1 F 0.4008(5) 0.0477(5) 0.6467(3) 0.0748(13) Uani 1 1 d .
F2 F 0.3343(9) 0.0880(8) 0.7773(4) 0.176(4) Uani 1 1 d .
F3 F 0.0583(6) -0.0678(6) 0.7171(4) 0.0975(17) Uani 1 1 d .
F4 F 0.1221(9) -0.0995(7) 0.5838(4) 0.168(3) Uani 1 1 d .
F5 F 0.1944(7) 0.1231(6) 0.6518(5) 0.123(2) Uani 1 1 d .
F6 F 0.2581(9) -0.1427(7) 0.7070(6) 0.172(4) Uani 1 1 d .
F7 F 0.3762(6) 0.6140(5) 0.8099(3) 0.0776(13) Uani 1 1 d .
F8 F 0.3299(7) 0.5776(8) 0.9464(4) 0.142(3) Uani 1 1 d .
F9 F 0.0414(6) 0.4540(5) 0.8818(4) 0.0931(16) Uani 1 1 d .
F10 F 0.0900(7) 0.4949(7) 0.7463(3) 0.121(2) Uani 1 1 d .
F11 F 0.1865(8) 0.6817(5) 0.8633(4) 0.113(2) Uani 1 1 d .
F12 F 0.2316(8) 0.3871(6) 0.8329(6) 0.145(3) Uani 1 1 d .
N1 N 0.7029(6) 0.5034(5) 0.6957(3) 0.0403(13) Uani 1 1 d .
N2 N 0.7625(7) 0.5891(5) 0.8409(3) 0.0419(13) Uani 1 1 d .
N3 N 0.8045(7) 0.8856(6) 0.8706(3) 0.0426(13) Uani 1 1 d .
N4 N 0.7140(7) 0.9832(5) 0.7068(3) 0.0426(13) Uani 1 1 d .
N5 N 0.5489(7) 0.7996(5) 0.5939(3) 0.0437(14) Uani 1 1 d .
N6 N 0.4133(6) 0.6401(6) 0.4528(3) 0.0414(13) Uani 1 1 d .
C1 C 0.8059(8) 0.6168(7) 0.7641(4) 0.0431(16) Uani 1 1 d .
H1A H 0.8953 0.7028 0.7585 0.052 Uiso 1 1 calc R
C2 C 0.5869(9) 0.3990(7) 0.7309(5) 0.057(2) Uani 1 1 d .
H2A H 0.4979 0.3083 0.6977 0.068 Uiso 1 1 calc R
C3 C 0.6274(9) 0.4536(7) 0.8221(4) 0.0493(18) Uani 1 1 d .
H3B H 0.5727 0.4071 0.8650 0.059 Uiso 1 1 calc R
C4 C 0.8434(9) 0.6859(7) 0.9323(4) 0.0491(18) Uani 1 1 d .
H4A H 0.9703 0.7214 0.9441 0.059 Uiso 1 1 calc R
H4B H 0.8072 0.6296 0.9790 0.059 Uiso 1 1 calc R
C5 C 0.7952(8) 0.8165(7) 0.9415(4) 0.0431(16) Uani 1 1 d .
C6 C 0.7529(9) 0.8631(8) 1.0192(4) 0.0517(18) Uani 1 1 d .
H6B H 0.7493 0.8131 1.0682 0.062 Uiso 1 1 calc R
C7 C 0.7158(9) 0.9860(8) 1.0229(5) 0.059(2) Uani 1 1 d .
H7A H 0.6860 1.0211 1.0750 0.070 Uiso 1 1 calc R
C8 C 0.7224(9) 1.0570(8) 0.9506(5) 0.0540(19) Uani 1 1 d .
H8A H 0.6964 1.1403 0.9521 0.065 Uiso 1 1 calc R
C9 C 0.7673(8) 1.0042(7) 0.8765(4) 0.0443(17) Uani 1 1 d .
C10 C 0.7882(10) 1.0833(7) 0.7975(4) 0.0564(19) Uani 1 1 d .
H10A H 0.7314 1.1518 0.8006 0.068 Uiso 1 1 calc R
H10B H 0.9125 1.1413 0.8045 0.068 Uiso 1 1 calc R
C11 C 0.5846(9) 0.8526(7) 0.6842(4) 0.0436(16) Uani 1 1 d .
H11A H 0.5260 0.8038 0.7253 0.052 Uiso 1 1 calc R
C12 C 0.7644(9) 1.0171(8) 0.6276(5) 0.060(2) Uani 1 1 d .
H12A H 0.8548 1.1037 0.6236 0.072 Uiso 1 1 calc R
C13 C 0.6612(9) 0.9044(8) 0.5582(5) 0.062(2) Uani 1 1 d .
H13A H 0.6644 0.8976 0.4960 0.074 Uiso 1 1 calc R
C14 C 0.4166(8) 0.6629(7) 0.5418(4) 0.0432(16) Uani 1 1 d .
C15 C 0.3065(9) 0.5643(8) 0.5812(5) 0.059(2) Uani 1 1 d .
H15A H 0.3139 0.5844 0.6446 0.071 Uiso 1 1 calc R
C16 C 0.1844(10) 0.4344(9) 0.5240(5) 0.071(2) Uani 1 1 d .
H16A H 0.1069 0.3640 0.5487 0.086 Uiso 1 1 calc R
C17 C 0.1749(10) 0.4066(8) 0.4306(5) 0.065(2) Uani 1 1 d .
H17A H 0.0918 0.3193 0.3903 0.078 Uiso 1 1 calc R
C18 C 0.2951(8) 0.5151(7) 0.4003(4) 0.0428(16) Uani 1 1 d .
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_3
F6 P1 F2 93.0(5) .
F6 P1 F4 90.4(5) .
F2 P1 F4 176.4(4) .
F6 P1 F3 87.2(3) .
F2 P1 F3 91.4(3) .
F4 P1 F3 89.9(3) .
F6 P1 F5 177.3(5) .
F2 P1 F5 89.5(4) .
F4 P1 F5 87.0(4) .
F3 P1 F5 93.5(3) .
F6 P1 F1 92.2(3) .
F2 P1 F1 88.7(3) .
F4 P1 F1 89.9(3) .
F3 P1 F1 179.4(3) .
F5 P1 F1 87.1(3) .
F12 P2 F8 89.0(4) .
F12 P2 F10 92.8(4) .
F8 P2 F10 178.1(4) .
F12 P2 F11 177.9(4) .
F8 P2 F11 89.4(4) .
F10 P2 F11 88.8(4) .
F12 P2 F7 91.9(3) .
F8 P2 F7 89.4(3) .
F10 P2 F7 90.2(3) .
F11 P2 F7 89.5(3) .
F12 P2 F9 88.7(3) .
F8 P2 F9 91.1(3) .
F10 P2 F9 89.3(3) .
F11 P2 F9 90.0(3) .
F7 P2 F9 179.3(3) .
C1 N1 C2 108.6(5) .
C1 N1 C18 128.0(5) 2_666
C2 N1 C18 123.4(5) 2_666
C1 N2 C3 108.9(5) .
C1 N2 C4 126.2(6) .
C3 N2 C4 124.8(5) .
C9 N3 C5 117.5(5) .
C11 N4 C12 108.0(5) .
C11 N4 C10 127.6(5) .
C12 N4 C10 124.3(6) .
C11 N5 C13 107.4(5) .
C11 N5 C14 127.3(5) .
C13 N5 C14 125.2(5) .
C18 N6 C14 117.0(5) .
N1 C1 N2 108.7(5) .
N1 C1 H1A 125.6 .
N2 C1 H1A 125.6 .
C3 C2 N1 106.1(6) .
C3 C2 H2A 127.0 .
N1 C2 H2A 127.0 .
C2 C3 N2 107.7(6) .
C2 C3 H3B 126.2 .
N2 C3 H3B 126.2 .
N2 C4 C5 112.5(5) .
N2 C4 H4A 109.1 .
C5 C4 H4A 109.1 .
N2 C4 H4B 109.1 .
C5 C4 H4B 109.1 .
H4A C4 H4B 107.8 .
N3 C5 C6 123.3(6) .
N3 C5 C4 115.1(5) .
C6 C5 C4 121.5(6) .
C5 C6 C7 117.5(7) .
C5 C6 H6B 121.2 .
C7 C6 H6B 121.2 .
C6 C7 C8 120.0(7) .
C6 C7 H7A 120.0 .
C8 C7 H7A 120.0 .
C9 C8 C7 118.6(7) .
C9 C8 H8A 120.7 .
C7 C8 H8A 120.7 .
N3 C9 C8 123.1(6) .
N3 C9 C10 115.8(6) .
C8 C9 C10 121.0(6) .
N4 C10 C9 113.0(5) .
N4 C10 H10A 109.0 .
C9 C10 H10A 109.0 .
N4 C10 H10B 109.0 .
C9 C10 H10B 109.0 .
H10A C10 H10B 107.8 .
N4 C11 N5 109.5(6) .
N4 C11 H11A 125.2 .
N5 C11 H11A 125.2 .
C13 C12 N4 107.3(6) .
C13 C12 H12A 126.4 .
N4 C12 H12A 126.3 .
C12 C13 N5 107.7(6) .
C12 C13 H13A 126.1 .
N5 C13 H13A 126.1 .
N6 C14 C15 124.1(6) .
N6 C14 N5 113.5(5) .
C15 C14 N5 122.4(6) .
C16 C15 C14 117.4(6) .
C16 C15 H15A 121.3 .
C14 C15 H15A 121.3 .
C15 C16 C17 120.6(7) .
C15 C16 H16A 119.7 .
C17 C16 H16A 119.7 .
C16 C17 C18 116.0(7) .
C16 C17 H17A 122.0 .
C18 C17 H17A 122.0 .
N6 C18 C17 125.0(6) .
N6 C18 N1 114.6(5) 2_666
C17 C18 N1 120.4(6) 2_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 F6 1.524(5) .
P1 F2 1.531(6) .
P1 F4 1.547(6) .
P1 F3 1.569(5) .
P1 F5 1.565(5) .
P1 F1 1.596(4) .
P2 F12 1.544(5) .
P2 F8 1.565(5) .
P2 F10 1.563(5) .
P2 F11 1.568(5) .
P2 F7 1.590(4) .
P2 F9 1.593(5) .
N1 C1 1.325(7) .
N1 C2 1.386(8) .
N1 C18 1.442(7) 2_666
N2 C1 1.314(7) .
N2 C3 1.366(8) .
N2 C4 1.460(7) .
N3 C9 1.339(8) .
N3 C5 1.342(8) .
N4 C11 1.311(8) .
N4 C12 1.385(8) .
N4 C10 1.464(8) .
N5 C11 1.334(7) .
N5 C13 1.378(8) .
N5 C14 1.420(7) .
N6 C18 1.314(7) .
N6 C14 1.329(7) .
C1 H1A 0.9400 .
C2 C3 1.345(9) .
C2 H2A 0.9400 .
C3 H3B 0.9400 .
C4 C5 1.513(9) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C5 C6 1.372(8) .
C6 C7 1.381(9) .
C6 H6B 0.9400 .
C7 C8 1.372(9) .
C7 H7A 0.9400 .
C8 C9 1.362(9) .
C8 H8A 0.9400 .
C9 C10 1.512(9) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C11 H11A 0.9400 .
C12 C13 1.330(9) .
C12 H12A 0.9400 .
C13 H13A 0.9400 .
C14 C15 1.370(9) .
C15 C16 1.378(9) .
C15 H15A 0.9400 .
C16 C17 1.385(9) .
C16 H16A 0.9400 .
C17 C18 1.383(9) .
C17 H17A 0.9400 .
C18 N1 1.442(7) 2_666
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_4
C2 N1 C1 N2 0.7(7) . .
C18 N1 C1 N2 -179.2(6) 2_666 .
C3 N2 C1 N1 0.1(7) . .
C4 N2 C1 N1 -179.8(6) . .
C1 N1 C2 C3 -1.1(8) . .
C18 N1 C2 C3 178.7(6) 2_666 .
N1 C2 C3 N2 1.2(8) . .
C1 N2 C3 C2 -0.8(8) . .
C4 N2 C3 C2 179.0(6) . .
C1 N2 C4 C5 72.9(8) . .
C3 N2 C4 C5 -106.9(7) . .
C9 N3 C5 C6 -1.2(9) . .
C9 N3 C5 C4 -178.3(6) . .
N2 C4 C5 N3 -45.7(8) . .
N2 C4 C5 C6 137.1(6) . .
N3 C5 C6 C7 1.0(10) . .
C4 C5 C6 C7 178.0(6) . .
C5 C6 C7 C8 -0.1(10) . .
C6 C7 C8 C9 -0.6(11) . .
C5 N3 C9 C8 0.4(10) . .
C5 N3 C9 C10 177.0(6) . .
C7 C8 C9 N3 0.4(11) . .
C7 C8 C9 C10 -176.0(6) . .
C11 N4 C10 C9 27.7(10) . .
C12 N4 C10 C9 -156.8(6) . .
N3 C9 C10 N4 44.9(8) . .
C8 C9 C10 N4 -138.5(7) . .
C12 N4 C11 N5 0.3(8) . .
C10 N4 C11 N5 176.4(6) . .
C13 N5 C11 N4 -0.9(8) . .
C14 N5 C11 N4 -179.0(6) . .
C11 N4 C12 C13 0.5(8) . .
C10 N4 C12 C13 -175.8(7) . .
N4 C12 C13 N5 -1.0(9) . .
C11 N5 C13 C12 1.2(8) . .
C14 N5 C13 C12 179.3(6) . .
C18 N6 C14 C15 0.6(10) . .
C18 N6 C14 N5 179.4(6) . .
C11 N5 C14 N6 -179.7(6) . .
C13 N5 C14 N6 2.5(10) . .
C11 N5 C14 C15 -0.9(11) . .
C13 N5 C14 C15 -178.6(7) . .
N6 C14 C15 C16 -0.5(11) . .
N5 C14 C15 C16 -179.3(7) . .
C14 C15 C16 C17 -0.2(12) . .
C15 C16 C17 C18 0.8(12) . .
C14 N6 C18 C17 0.1(10) . .
C14 N6 C18 N1 179.8(5) . 2_666
C16 C17 C18 N6 -0.7(12) . .
C16 C17 C18 N1 179.6(7) . 2_666
