#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/29/2222959.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_2222959
loop_
_publ_author_name
'Jiang, Ping'
_publ_section_title
;
 1-Benzyl-3-phenylimidazolium hexafluorophosphate
;
_journal_coeditor_code           AT2854
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2177
_journal_paper_doi               10.1107/S1600536809031584
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H15 N2 +, P F6 -'
_chemical_formula_moiety         'C16 H15 N2 +, F6 P -'
_chemical_formula_sum            'C16 H15 F6 N2 P'
_chemical_formula_weight         380.27
_chemical_name_systematic
;
1-Benzyl-3-phenylimidazolium hexafluorophosphate
;
_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                110.733(2)
_cell_angle_beta                 91.969(2)
_cell_angle_gamma                110.315(2)
_cell_formula_units_Z            2
_cell_length_a                   9.221(2)
_cell_length_b                   10.046(3)
_cell_length_c                   10.108(2)
_cell_measurement_reflns_used    2516
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      3.10
_cell_volume                     807.9(3)
_computing_cell_refinement       'RAPID-AUTO (Rigaku/MSC, 2004)'
_computing_data_collection       'RAPID-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'RAPID-AUTO (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Rigaku SPIDER'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4739
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.10
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9185
_exptl_absorpt_correction_T_min  0.9049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0347
_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)+(0.043P)²+0.066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                2361
_reflns_number_total             2902
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2854.cif
_cod_data_source_block           I
_cod_database_code               2222959
_cod_database_fobs_code          2222959
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 1.23197(5) 1.00569(5) 0.79232(5) 0.02127(14) Uani d . 1 . .
F F1 1.38948(11) 1.06413(12) 0.73171(11) 0.0297(3) Uani d . 1 . .
F F2 1.07593(13) 0.94747(15) 0.85307(13) 0.0444(3) Uani d . 1 . .
F F3 1.16399(13) 1.10464(14) 0.73467(12) 0.0380(3) Uani d . 1 . .
F F4 1.30246(13) 0.90834(14) 0.85235(12) 0.0381(3) Uani d . 1 . .
F F5 1.30920(14) 1.15038(13) 0.94289(11) 0.0427(3) Uani d . 1 . .
F F6 1.15883(14) 0.86186(13) 0.64242(12) 0.0433(3) Uani d . 1 . .
N N1 0.47043(15) 0.20046(16) 0.35708(14) 0.0188(3) Uani d . 1 . .
N N2 0.28468(15) -0.02584(16) 0.25378(14) 0.0192(3) Uani d . 1 . .
C C1 0.5504(2) 0.4242(2) 0.29382(18) 0.0235(4) Uani d . 1 . .
H H1 0.4593 0.3740 0.2211 0.028 Uiso calc R 1 . .
C C2 0.6550(2) 0.5713(2) 0.31694(19) 0.0255(4) Uani d . 1 . .
H H2 0.6367 0.6216 0.2581 0.031 Uiso calc R 1 . .
C C3 0.7858(2) 0.6454(2) 0.42503(18) 0.0241(4) Uani d . 1 . .
H H3 0.8553 0.7475 0.4422 0.029 Uiso calc R 1 . .
C C4 0.8153(2) 0.5709(2) 0.50786(19) 0.0270(4) Uani d . 1 . .
H H4 0.9061 0.6213 0.5810 0.032 Uiso calc R 1 . .
C C5 0.7131(2) 0.4229(2) 0.48495(19) 0.0243(4) Uani d . 1 . .
H H5 0.7337 0.3714 0.5416 0.029 Uiso calc R 1 . .
C C6 0.58132(19) 0.3514(2) 0.37897(18) 0.0191(4) Uani d . 1 . .
C C7 0.4319(2) 0.1417(2) 0.46130(18) 0.0218(4) Uani d . 1 . .
H H7 0.4787 0.1912 0.5602 0.026 Uiso calc R 1 . .
C C8 0.3160(2) 0.0014(2) 0.39716(18) 0.0223(4) Uani d . 1 . .
H H8 0.2652 -0.0662 0.4423 0.027 Uiso calc R 1 . .
C C9 0.37939(19) 0.0950(2) 0.23205(18) 0.0194(4) Uani d . 1 . .
H H9 0.3822 0.1051 0.1421 0.023 Uiso calc R 1 . .
C C10 0.1627(2) -0.1631(2) 0.14214(19) 0.0233(4) Uani d . 1 . .
H H10A 0.1772 -0.1595 0.0467 0.028 Uiso calc R 1 . .
H H10B 0.0580 -0.1612 0.1581 0.028 Uiso calc R 1 . .
C C11 0.16757(19) -0.3114(2) 0.14213(17) 0.0197(4) Uani d . 1 . .
C C12 0.28553(19) -0.3616(2) 0.08983(18) 0.0224(4) Uani d . 1 . .
H H12 0.3691 -0.2983 0.0598 0.027 Uiso calc R 1 . .
C C13 0.2811(2) -0.5030(2) 0.08160(18) 0.0254(4) Uani d . 1 . .
H H13 0.3614 -0.5368 0.0453 0.030 Uiso calc R 1 . .
C C14 0.1600(2) -0.5965(2) 0.12598(18) 0.0255(4) Uani d . 1 . .
H H14 0.1569 -0.6941 0.1195 0.031 Uiso calc R 1 . .
C C15 0.0439(2) -0.5460(2) 0.17967(18) 0.0248(4) Uani d . 1 . .
H H15 -0.0385 -0.6087 0.2113 0.030 Uiso calc R 1 . .
C C16 0.04776(19) -0.4049(2) 0.18733(17) 0.0219(4) Uani d . 1 . .
H H16 -0.0325 -0.3713 0.2240 0.026 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F2 P1 F3 . . 90.46(6) ?
F2 P1 F6 . . 90.77(7) ?
F3 P1 F6 . . 90.53(7) ?
F2 P1 F1 . . 179.73(6) ?
F3 P1 F1 . . 89.79(6) ?
F6 P1 F1 . . 89.34(6) ?
F2 P1 F5 . . 90.23(7) ?
F3 P1 F5 . . 90.14(7) ?
F6 P1 F5 . . 178.80(7) ?
F1 P1 F5 . . 89.66(6) ?
F2 P1 F4 . . 89.83(6) ?
F3 P1 F4 . . 179.11(7) ?
F6 P1 F4 . . 90.31(7) ?
F1 P1 F4 . . 89.92(6) ?
F5 P1 F4 . . 89.02(7) ?
C9 N1 C7 . . 107.81(14) ?
C9 N1 C6 . . 125.48(14) ?
C7 N1 C6 . . 126.60(15) ?
C9 N2 C8 . . 108.63(14) ?
C9 N2 C10 . . 124.79(14) ?
C8 N2 C10 . . 126.53(14) ?
C2 C1 C6 . . 118.79(17) ?
C2 C1 H1 . . 120.6 ?
C6 C1 H1 . . 120.6 ?
C3 C2 C1 . . 120.50(17) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C4 C3 C2 . . 119.89(17) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 120.38(17) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C6 C5 C4 . . 119.21(17) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
C5 C6 C1 . . 121.20(17) ?
C5 C6 N1 . . 120.21(15) ?
C1 C6 N1 . . 118.58(15) ?
C8 C7 N1 . . 107.46(15) ?
C8 C7 H7 . . 126.3 ?
N1 C7 H7 . . 126.3 ?
C7 C8 N2 . . 107.13(15) ?
C7 C8 H8 . . 126.4 ?
N2 C8 H8 . . 126.4 ?
N2 C9 N1 . . 108.96(14) ?
N2 C9 H9 . . 125.5 ?
N1 C9 H9 . . 125.5 ?
N2 C10 C11 . . 112.54(14) ?
N2 C10 H10A . . 109.1 ?
C11 C10 H10A . . 109.1 ?
N2 C10 H10B . . 109.1 ?
C11 C10 H10B . . 109.1 ?
H10A C10 H10B . . 107.8 ?
C16 C11 C12 . . 118.95(16) ?
C16 C11 C10 . . 119.61(15) ?
C12 C11 C10 . . 121.34(15) ?
C13 C12 C11 . . 120.18(16) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C12 C13 C14 . . 120.50(17) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 C13 . . 119.44(17) ?
C15 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
C16 C15 C14 . . 120.11(16) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C11 . . 120.81(16) ?
C15 C16 H16 . . 119.6 ?
C11 C16 H16 . . 119.6 ?
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 F2 . 1.5875(11) ?
P1 F3 . 1.5933(11) ?
P1 F6 . 1.5942(12) ?
P1 F1 . 1.5978(11) ?
P1 F5 . 1.6052(12) ?
P1 F4 . 1.6066(11) ?
N1 C9 . 1.336(2) ?
N1 C7 . 1.380(2) ?
N1 C6 . 1.437(2) ?
N2 C9 . 1.323(2) ?
N2 C8 . 1.376(2) ?
N2 C10 . 1.474(2) ?
C1 C2 . 1.385(2) ?
C1 C6 . 1.389(2) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.383(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.380(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.386(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.378(2) ?
C5 H5 . 0.9500 ?
C7 C8 . 1.345(2) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 C11 . 1.505(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C16 . 1.389(2) ?
C11 C12 . 1.396(2) ?
C12 C13 . 1.379(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.391(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.386(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.380(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
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
_geom_hbond_publ_flag
C7 H7 F1 1_445 0.95 2.50 3.099(2) 121 yes
C8 H8 F6 1_445 0.95 2.50 3.392(2) 156 yes
C9 H9 F5 1_444 0.95 2.34 3.247(2) 159 yes
C10 H10A F4 1_444 0.99 2.49 3.444(2) 161 yes
C10 H10B F3 2_666 0.99 2.49 3.455(3) 164 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.4(3) ?
C1 C2 C3 C4 . . . . 1.9(3) ?
C2 C3 C4 C5 . . . . -1.0(3) ?
C3 C4 C5 C6 . . . . -0.3(3) ?
C4 C5 C6 C1 . . . . 0.8(3) ?
C4 C5 C6 N1 . . . . -177.50(15) ?
C2 C1 C6 C5 . . . . 0.0(3) ?
C2 C1 C6 N1 . . . . 178.40(15) ?
C9 N1 C6 C5 . . . . -151.02(16) ?
C7 N1 C6 C5 . . . . 33.1(2) ?
C9 N1 C6 C1 . . . . 30.6(2) ?
C7 N1 C6 C1 . . . . -145.30(16) ?
C9 N1 C7 C8 . . . . -0.76(18) ?
C6 N1 C7 C8 . . . . 175.73(15) ?
N1 C7 C8 N2 . . . . 0.46(18) ?
C9 N2 C8 C7 . . . . 0.01(18) ?
C10 N2 C8 C7 . . . . -177.88(15) ?
C8 N2 C9 N1 . . . . -0.49(18) ?
C10 N2 C9 N1 . . . . 177.44(14) ?
C7 N1 C9 N2 . . . . 0.77(18) ?
C6 N1 C9 N2 . . . . -175.77(14) ?
C9 N2 C10 C11 . . . . 132.27(16) ?
C8 N2 C10 C11 . . . . -50.2(2) ?
N2 C10 C11 C16 . . . . 109.96(17) ?
N2 C10 C11 C12 . . . . -73.7(2) ?
C16 C11 C12 C13 . . . . 0.9(2) ?
C10 C11 C12 C13 . . . . -175.41(16) ?
C11 C12 C13 C14 . . . . -0.4(3) ?
C12 C13 C14 C15 . . . . -0.4(3) ?
C13 C14 C15 C16 . . . . 0.7(2) ?
C14 C15 C16 C11 . . . . -0.2(2) ?
C12 C11 C16 C15 . . . . -0.6(2) ?
C10 C11 C16 C15 . . . . 175.78(15) ?
