#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/90/2229040.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229040
loop_
_publ_author_name
'Zhu, Run-Qiang'
_publ_section_title
;
 1-Chloromethyl-1,4-diazoniabicyclo[2.2.2]octane
 bis(hexafluorophosphate)
;
_journal_coeditor_code           FJ2377
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o346
_journal_paper_doi               10.1107/S1600536811000390
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C7 H15 Cl N2 2+, 2P F6 -'
_chemical_formula_moiety         'C7 H15 Cl N2 2+, 2(F6 P -)'
_chemical_formula_sum            'C7 H15 Cl F12 N2 P2'
_chemical_formula_weight         452.6
_chemical_name_systematic
;
1-Chloromethyl-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate)
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.414(8)
_cell_length_b                   12.976(7)
_cell_length_c                   16.115(9)
_cell_measurement_reflns_used    6697
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      2.4596
_cell_volume                     3014(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       'CCD Profile fitting'
_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  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30798
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.995
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.3000
_exptl_crystal_size_mid          0.2500
_exptl_crystal_size_min          0.2000
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.458
_refine_ls_extinction_coef       0.00140(10)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.239
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0560
_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)+(0.0625P)²+3.8206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1459
_reflns_number_gt                3197
_reflns_number_total             3447
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2377.cif
_cod_data_source_block           I
_cod_database_code               2229040
_cod_database_fobs_code          2229040
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.10243(5) 0.80778(6) 0.38500(5) 0.01982(19) Uani d . 1 . .
P P2 0.25717(5) 0.96221(6) 0.14312(5) 0.01997(19) Uani d . 1 . .
F F8 0.19471(13) 0.87588(16) 0.38218(13) 0.0359(5) Uani d . 1 . .
F F9 0.06202(13) 0.87478(14) 0.30870(11) 0.0293(4) Uani d . 1 . .
F F11 0.05718(12) 0.88833(14) 0.44911(11) 0.0268(4) Uani d . 1 . .
F F10 0.00885(13) 0.74127(15) 0.38738(13) 0.0331(4) Uani d . 1 . .
F F7 0.14303(13) 0.74224(16) 0.46061(11) 0.0343(5) Uani d . 1 . .
F F12 0.14650(13) 0.72793(15) 0.32030(12) 0.0322(4) Uani d . 1 . .
F F3 0.15177(12) 1.00058(16) 0.15861(13) 0.0347(5) Uani d . 1 . .
F F1 0.23000(15) 0.92628(16) 0.05253(11) 0.0363(5) Uani d . 1 . .
F F4 0.28151(16) 0.99851(17) 0.23639(13) 0.0430(6) Uani d . 1 . .
F F2 0.36096(14) 0.92349(19) 0.13078(16) 0.0479(6) Uani d . 1 . .
F F5 0.22953(16) 0.85130(15) 0.17743(14) 0.0421(5) Uani d . 1 . .
F F6 0.28287(17) 1.07397(16) 0.11115(15) 0.0465(6) Uani d . 1 . .
Cl Cl1 0.09951(6) 0.45726(7) 0.44115(7) 0.0419(3) Uani d . 1 . .
N N1 0.05494(16) 0.26975(18) 0.37949(15) 0.0189(5) Uani d . 1 . .
N N2 0.11243(16) 0.10322(19) 0.31629(15) 0.0206(5) Uani d . 1 . .
H H2C 0.1332 0.0434 0.2933 0.025 Uiso calc R 1 . .
C C5 -0.02655(19) 0.2006(2) 0.35656(18) 0.0207(6) Uani d . 1 . .
H H5A -0.0654 0.1896 0.4049 0.025 Uiso calc R 1 . .
H H5B -0.0638 0.2336 0.3141 0.025 Uiso calc R 1 . .
C C1 0.1107(2) 0.2924(2) 0.30230(19) 0.0224(6) Uani d . 1 . .
H H1A 0.1657 0.3316 0.3168 0.027 Uiso calc R 1 . .
H H1B 0.0740 0.3333 0.2641 0.027 Uiso calc R 1 . .
C C3 0.1568(2) 0.1167(2) 0.39967(18) 0.0278(7) Uani d . 1 . .
H H3A 0.2234 0.1239 0.3935 0.033 Uiso calc R 1 . .
H H3B 0.1446 0.0569 0.4341 0.033 Uiso calc R 1 . .
C C7 0.0138(2) 0.3663(2) 0.4162(2) 0.0266(6) Uani d . 1 . .
H H7A -0.0207 0.3486 0.4660 0.032 Uiso calc R 1 . .
H H7B -0.0293 0.3964 0.3769 0.032 Uiso calc R 1 . .
C C2 0.1390(2) 0.1914(2) 0.2609(2) 0.0280(7) Uani d . 1 . .
H H2A 0.1080 0.1847 0.2077 0.034 Uiso calc R 1 . .
H H2B 0.2054 0.1908 0.2513 0.034 Uiso calc R 1 . .
C C4 0.1162(2) 0.2138(2) 0.44068(18) 0.0232(6) Uani d . 1 . .
H H4A 0.0804 0.1946 0.4892 0.028 Uiso calc R 1 . .
H H4B 0.1662 0.2588 0.4584 0.028 Uiso calc R 1 . .
C C6 0.0090(2) 0.0978(3) 0.3247(3) 0.0364(8) Uani d . 1 . .
H H6A -0.0078 0.0434 0.3631 0.044 Uiso calc R 1 . .
H H6B -0.0188 0.0825 0.2713 0.044 Uiso calc R 1 . .
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'
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F7 P1 F8 . . 90.65(12) ?
F7 P1 F12 . . 90.40(11) ?
F8 P1 F12 . . 90.53(12) ?
F7 P1 F10 . . 90.19(12) ?
F8 P1 F10 . . 178.98(12) ?
F12 P1 F10 . . 90.06(11) ?
F7 P1 F11 . . 90.26(11) ?
F8 P1 F11 . . 89.79(11) ?
F12 P1 F11 . . 179.26(11) ?
F10 P1 F11 . . 89.62(11) ?
F7 P1 F9 . . 179.52(13) ?
F8 P1 F9 . . 88.90(11) ?
F12 P1 F9 . . 89.75(11) ?
F10 P1 F9 . . 90.26(11) ?
F11 P1 F9 . . 89.59(10) ?
F1 P2 F6 . . 91.58(13) ?
F1 P2 F2 . . 91.39(12) ?
F6 P2 F2 . . 91.64(14) ?
F1 P2 F5 . . 89.54(12) ?
F6 P2 F5 . . 178.30(13) ?
F2 P2 F5 . . 89.61(13) ?
F1 P2 F4 . . 178.20(13) ?
F6 P2 F4 . . 89.13(13) ?
F2 P2 F4 . . 90.24(13) ?
F5 P2 F4 . . 89.71(13) ?
F1 P2 F3 . . 90.03(11) ?
F6 P2 F3 . . 89.32(13) ?
F2 P2 F3 . . 178.26(14) ?
F5 P2 F3 . . 89.40(12) ?
F4 P2 F3 . . 88.32(11) ?
C7 N1 C4 . . 111.9(2) ?
C7 N1 C1 . . 111.8(2) ?
C4 N1 C1 . . 108.7(2) ?
C7 N1 C5 . . 106.3(2) ?
C4 N1 C5 . . 109.0(2) ?
C1 N1 C5 . . 109.0(2) ?
C6 N2 C3 . . 110.4(3) ?
C6 N2 C2 . . 110.1(3) ?
C3 N2 C2 . . 109.6(2) ?
C6 N2 H2C . . 108.9 ?
C3 N2 H2C . . 108.9 ?
C2 N2 H2C . . 108.9 ?
C6 C5 N1 . . 109.8(2) ?
C6 C5 H5A . . 109.7 ?
N1 C5 H5A . . 109.7 ?
C6 C5 H5B . . 109.7 ?
N1 C5 H5B . . 109.7 ?
H5A C5 H5B . . 108.2 ?
N1 C1 C2 . . 109.6(2) ?
N1 C1 H1A . . 109.8 ?
C2 C1 H1A . . 109.8 ?
N1 C1 H1B . . 109.8 ?
C2 C1 H1B . . 109.8 ?
H1A C1 H1B . . 108.2 ?
N2 C3 C4 . . 108.6(2) ?
N2 C3 H3A . . 110.0 ?
C4 C3 H3A . . 110.0 ?
N2 C3 H3B . . 110.0 ?
C4 C3 H3B . . 110.0 ?
H3A C3 H3B . . 108.3 ?
N1 C7 Cl1 . . 111.8(2) ?
N1 C7 H7A . . 109.3 ?
Cl1 C7 H7A . . 109.3 ?
N1 C7 H7B . . 109.3 ?
Cl1 C7 H7B . . 109.3 ?
H7A C7 H7B . . 107.9 ?
N2 C2 C1 . . 109.1(2) ?
N2 C2 H2A . . 109.9 ?
C1 C2 H2A . . 109.9 ?
N2 C2 H2B . . 109.9 ?
C1 C2 H2B . . 109.9 ?
H2A C2 H2B . . 108.3 ?
N1 C4 C3 . . 109.6(2) ?
N1 C4 H4A . . 109.8 ?
C3 C4 H4A . . 109.8 ?
N1 C4 H4B . . 109.8 ?
C3 C4 H4B . . 109.8 ?
H4A C4 H4B . . 108.2 ?
N2 C6 C5 . . 109.0(2) ?
N2 C6 H6A . . 109.9 ?
C5 C6 H6A . . 109.9 ?
N2 C6 H6B . . 109.9 ?
C5 C6 H6B . . 109.9 ?
H6A C6 H6B . . 108.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 F7 . 1.597(2) ?
P1 F8 . 1.598(2) ?
P1 F12 . 1.601(2) ?
P1 F10 . 1.602(2) ?
P1 F11 . 1.6079(19) ?
P1 F9 . 1.6147(19) ?
P2 F1 . 1.582(2) ?
P2 F6 . 1.583(2) ?
P2 F2 . 1.591(2) ?
P2 F5 . 1.592(2) ?
P2 F4 . 1.614(2) ?
P2 F3 . 1.618(2) ?
Cl1 C7 . 1.756(3) ?
N1 C7 . 1.507(4) ?
N1 C4 . 1.510(4) ?
N1 C1 . 1.510(4) ?
N1 C5 . 1.524(3) ?
N2 C6 . 1.498(4) ?
N2 C3 . 1.498(4) ?
N2 C2 . 1.501(4) ?
N2 H2C . 0.9100 ?
C5 C6 . 1.518(4) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C1 C2 . 1.527(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C3 C4 . 1.538(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2C F3 1_545 0.91 2.26 2.924(3) 130
N2 H2C F4 1_545 0.91 2.40 3.073(3) 131
N2 H2C F9 1_545 0.91 2.43 3.055(3) 126
