#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/91/1509133.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_1509133
loop_
_publ_author_name
'Gunbas, Gorkem'
'Hafezi, Nema'
'Sheppard, William L'
'Olmstead, Marilyn M'
'Stoyanova, Irini V'
'Tham, Fook S'
'Meyer, Matthew P'
'Mascal, Mark'
_publ_section_title
;
 Extreme oxatriquinanes and a record C-O bond length.
;
_journal_issue                   12
_journal_name_full               'Nature chemistry'
_journal_page_first              1018
_journal_page_last               1023
_journal_paper_doi               10.1038/nchem.1502
_journal_volume                  4
_journal_year                    2012
_chemical_formula_moiety         'C18 H33 O , P F6'
_chemical_formula_sum            'C18 H33 F6 O P'
_chemical_formula_weight         410.41
_chemical_melting_point          492
_chemical_name_systematic
; 
 1,4,7- tri-iso-propyloxatriquinanium Hexafluorophosphate
;
_space_group_IT_number           161
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'R 3 -2"c'
_symmetry_space_group_name_H-M   'R 3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   10.2958(19)
_cell_length_b                   10.2958(19)
_cell_length_c                   32.340(6)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      31.6
_cell_measurement_theta_min      2.6
_cell_volume                     2968.9(10)
_computing_cell_refinement       'SAINT (Bruker, 2011)'
_computing_data_collection       'Apex2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART DUO'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0115
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            15378
_diffrn_reflns_theta_full        31.61
_diffrn_reflns_theta_max         31.61
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0194
_refine_ls_R_factor_gt           0.0191
_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)+(0.0449P)²+0.3179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0568
_reflns_number_gt                2180
_reflns_number_total             2208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nchem.1502-s4.cif
_cod_data_source_block           gg02
_cod_original_cell_volume        2968.8(10)
_cod_original_sg_symbol_H-M      'R 3c'
_cod_database_code               1509133
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'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'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'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'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'
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
O1 O 0.0000 0.0000 0.13986(3) 0.01244(14) Uani 1 3 d S
C1 C 0.16370(7) 0.06005(7) 0.12469(2) 0.01430(10) Uani 1 1 d .
C2 C 0.20497(7) 0.21277(7) 0.10681(2) 0.01767(11) Uani 1 1 d .
H2A H 0.2756 0.2382 0.0834 0.021 Uiso 1 1 calc R
H2B H 0.2524 0.2918 0.1282 0.021 Uiso 1 1 calc R
C3 C 0.05712(7) 0.19876(7) 0.09214(2) 0.01805(11) Uani 1 1 d .
H3A H 0.0664 0.2990 0.0899 0.022 Uiso 1 1 calc R
H3B H 0.0287 0.1494 0.0647 0.022 Uiso 1 1 calc R
C4 C 0.25630(7) 0.06346(7) 0.16232(2) 0.01689(11) Uani 1 1 d .
H4 H 0.2179 -0.0423 0.1715 0.020 Uiso 1 1 calc R
C5 C 0.24660(8) 0.15208(9) 0.19913(2) 0.02225(13) Uani 1 1 d .
H5A H 0.1413 0.1118 0.2068 0.033 Uiso 1 1 calc R
H5B H 0.2906 0.2579 0.1914 0.033 Uiso 1 1 calc R
H5C H 0.3018 0.1432 0.2226 0.033 Uiso 1 1 calc R
C6 C 0.42178(7) 0.12971(8) 0.14978(3) 0.02579(14) Uani 1 1 d .
H6A H 0.4294 0.0686 0.1277 0.039 Uiso 1 1 calc R
H6B H 0.4801 0.1301 0.1738 0.039 Uiso 1 1 calc R
H6C H 0.4612 0.2326 0.1399 0.039 Uiso 1 1 calc R
P1 P 0.3333 0.6667 0.131636(10) 0.01415(6) Uani 1 3 d S
F1 F 0.24981(5) 0.52058(6) 0.160693(16) 0.02529(11) Uani 1 1 d .
F2 F 0.39558(6) 0.58265(6) 0.103189(16) 0.02959(12) Uani 1 1 d .
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
O1 0.0114(2) 0.0114(2) 0.0145(4) 0.000 0.000 0.00569(10)
C1 0.0111(2) 0.0141(2) 0.0171(2) 0.0000(2) 0.00202(18) 0.0058(2)
C2 0.0151(2) 0.0147(2) 0.0220(3) 0.0037(2) 0.0041(2) 0.0066(2)
C3 0.0180(3) 0.0178(2) 0.0184(2) 0.0051(2) 0.0027(2) 0.0090(2)
C4 0.0134(2) 0.0161(2) 0.0216(3) -0.0029(2) -0.0036(2) 0.0076(2)
C5 0.0225(3) 0.0238(3) 0.0217(3) -0.0077(2) -0.0076(2) 0.0125(3)
C6 0.0135(3) 0.0245(3) 0.0384(4) -0.0044(3) -0.0020(3) 0.0087(2)
P1 0.01315(8) 0.01315(8) 0.01614(11) 0.000 0.000 0.00658(4)
F1 0.0285(2) 0.0161(2) 0.0259(2) 0.00509(17) 0.00315(17) 0.00718(17)
F2 0.0370(3) 0.0340(2) 0.0268(3) -0.00491(18) 0.00497(19) 0.0245(2)
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'
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_1
_geom_angle_site_symmetry_3
C1 O1 C1 110.54(4) . 3
C1 O1 C1 110.54(4) . 2
C1 O1 C1 110.54(4) 3 2
C2 C1 C3 114.06(5) . 3
C2 C1 C4 115.33(5) . .
C3 C1 C4 114.14(5) 3 .
C2 C1 O1 102.56(4) . .
C3 C1 O1 101.50(5) 3 .
C4 C1 O1 107.22(5) . .
C1 C2 C3 105.63(5) . .
C1 C2 H2A 110.6 . .
C3 C2 H2A 110.6 . .
C1 C2 H2B 110.6 . .
C3 C2 H2B 110.6 . .
H2A C2 H2B 108.7 . .
C1 C3 C2 106.01(5) 2 .
C1 C3 H3A 110.5 2 .
C2 C3 H3A 110.5 . .
C1 C3 H3B 110.5 2 .
C2 C3 H3B 110.5 . .
H3A C3 H3B 108.7 . .
C5 C4 C1 113.86(5) . .
C5 C4 C6 109.14(6) . .
C1 C4 C6 109.77(6) . .
C5 C4 H4 108.0 . .
C1 C4 H4 108.0 . .
C6 C4 H4 108.0 . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C4 C6 H6A 109.5 . .
C4 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C4 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
F2 P1 F2 90.23(3) . 2_665
F2 P1 F2 90.23(3) . 3_565
F2 P1 F2 90.23(3) 2_665 3_565
F2 P1 F1 90.30(3) . 2_665
F2 P1 F1 90.10(3) 2_665 2_665
F2 P1 F1 179.37(4) 3_565 2_665
F2 P1 F1 179.37(4) . 3_565
F2 P1 F1 90.30(3) 2_665 3_565
F2 P1 F1 90.10(3) 3_565 3_565
F1 P1 F1 89.36(3) 2_665 3_565
F2 P1 F1 90.10(3) . .
F2 P1 F1 179.37(4) 2_665 .
F2 P1 F1 90.31(3) 3_565 .
F1 P1 F1 89.36(3) 2_665 .
F1 P1 F1 89.36(3) 3_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.5562(7) .
O1 C1 1.5562(7) 3
O1 C1 1.5562(7) 2
C1 C2 1.5228(9) .
C1 C3 1.5300(9) 3
C1 C4 1.5355(9) .
C2 C3 1.5309(10) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C1 1.5300(9) 2
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.5330(9) .
C4 C6 1.5396(10) .
C4 H4 1.0000 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
P1 F2 1.5999(6) .
P1 F2 1.6000(6) 2_665
P1 F2 1.6000(6) 3_565
P1 F1 1.6097(5) 2_665
P1 F1 1.6097(5) 3_565
P1 F1 1.6098(5) .
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
C1 O1 C1 C2 131.74(4) 3 .
C1 O1 C1 C2 9.01(7) 2 .
C1 O1 C1 C3 13.60(7) 3 3
C1 O1 C1 C3 -109.12(5) 2 3
C1 O1 C1 C4 -106.40(7) 3 .
C1 O1 C1 C4 130.88(6) 2 .
C3 C1 C2 C3 80.45(7) 3 .
C4 C1 C2 C3 -144.57(5) . .
O1 C1 C2 C3 -28.40(6) . .
C1 C2 C3 C1 38.94(6) . 2
C2 C1 C4 C5 59.05(7) . .
C3 C1 C4 C5 -166.01(6) 3 .
O1 C1 C4 C5 -54.45(7) . .
C2 C1 C4 C6 -63.63(7) . .
C3 C1 C4 C6 71.31(7) 3 .
O1 C1 C4 C6 -177.12(5) . .
