#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/25/8102508.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_8102508
loop_
_publ_author_name
'Alexander Schwärzler'
'Gerhard Laus'
'Klaus Wurst'
'Günther Bonn'
'Herwig Schottenberger'
_publ_section_title
;
 Crystal structure of 1,3-dibenzyloxy-2-methylimidazolium
 hexafluorophosphate, [C18H19N2O2][PF6]
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              595
_journal_volume                  224
_journal_year                    2009
_chemical_formula_sum            'C18 H19 F6 N2 O2 P'
_chemical_formula_weight         440.32
_chemical_name_systematic
; 
1,3-dibenzyloxy-2-methylimidazolium hexafluorophosphate, 
(C₁₈H₁₉N₂O₂)(PF₆)
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_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                 92.737(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2953(2)
_cell_length_b                   20.7322(3)
_cell_length_c                   11.5293(4)
_cell_measurement_reflns_used    8234
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.0
_cell_volume                     1980.55(9)
_computing_data_collection       COLLECT
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6097
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_coef       0.0059(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3341
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.077
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0272P)²+0.5930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                3142
_reflns_number_total             3341
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2706.cff
_cod_data_source_block           s268
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               8102508
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.73771(18) 0.65150(7) 0.61545(13) 0.0516(4) Uani 1 1 d . . .
O2 O 0.77942(17) 0.82849(7) 0.86510(13) 0.0478(4) Uani 1 1 d . . .
N1 N 0.7665(2) 0.68611(8) 0.71532(15) 0.0428(4) Uani 1 1 d . . .
N2 N 0.7823(2) 0.76518(8) 0.82825(15) 0.0414(4) Uani 1 1 d . . .
C1 C 0.7784(3) 0.74942(10) 0.71665(17) 0.0402(5) Uani 1 1 d . . .
C2 C 0.7620(3) 0.66105(11) 0.8262(2) 0.0483(5) Uani 1 1 d . . .
H2 H 0.7540 0.6173 0.8467 0.058 Uiso 1 1 calc . . .
C3 C 0.7712(3) 0.71121(11) 0.89798(18) 0.0474(5) Uani 1 1 d . . .
H3 H 0.7703 0.7102 0.9795 0.057 Uiso 1 1 calc . . .
C4 C 0.7825(3) 0.79336(12) 0.6171(2) 0.0545(6) Uani 1 1 d . . .
H4A H 0.8935 0.8000 0.5969 0.082 Uiso 1 1 calc R . .
H4B H 0.7351 0.8344 0.6372 0.082 Uiso 1 1 calc R . .
H4C H 0.7216 0.7748 0.5514 0.082 Uiso 1 1 calc R . .
C5 C 0.8852(3) 0.62046(11) 0.57455(19) 0.0506(5) Uani 1 1 d . . .
H5A H 0.9784 0.6484 0.5927 0.061 Uiso 1 1 calc . . .
H5B H 0.8749 0.6152 0.4900 0.061 Uiso 1 1 calc . . .
C6 C 0.9133(2) 0.55618(10) 0.62996(18) 0.0417(5) Uani 1 1 d . . .
C7 C 0.8304(3) 0.50282(11) 0.5873(2) 0.0553(6) Uani 1 1 d . . .
H7 H 0.7584 0.5072 0.5223 0.066 Uiso 1 1 calc . . .
C8 C 0.8517(3) 0.44338(12) 0.6385(2) 0.0663(7) Uani 1 1 d . . .
H8 H 0.7931 0.4076 0.6092 0.080 Uiso 1 1 calc . . .
C9 C 0.9588(3) 0.43616(12) 0.7325(2) 0.0627(7) Uani 1 1 d . . .
H9 H 0.9749 0.3954 0.7668 0.075 Uiso 1 1 calc . . .
C10 C 1.0415(3) 0.48863(14) 0.7756(2) 0.0598(7) Uani 1 1 d . . .
H10 H 1.1136 0.4838 0.8404 0.072 Uiso 1 1 calc . . .
C11 C 1.0203(3) 0.54854(11) 0.7251(2) 0.0513(5) Uani 1 1 d . . .
H11 H 1.0784 0.5842 0.7552 0.062 Uiso 1 1 calc . . .
C12 C 0.9347(3) 0.84645(10) 0.9245(2) 0.0454(5) Uani 1 1 d . . .
H12A H 1.0256 0.8314 0.8804 0.055 Uiso 1 1 calc . . .
H12B H 0.9439 0.8278 1.0026 0.055 Uiso 1 1 calc . . .
C13 C 0.9322(3) 0.91859(9) 0.93019(18) 0.0396(4) Uani 1 1 d . . .
C14 C 0.9901(3) 0.95516(11) 0.84072(18) 0.0503(5) Uani 1 1 d . . .
H14 H 1.0361 0.9347 0.7775 0.060 Uiso 1 1 calc . . .
C15 C 0.9805(3) 1.02147(13) 0.8442(2) 0.0645(7) Uani 1 1 d . . .
H15 H 1.0194 1.0461 0.7831 0.077 Uiso 1 1 calc . . .
C16 C 0.9144(4) 1.05189(11) 0.9366(2) 0.0643(7) Uani 1 1 d . . .
H16 H 0.9083 1.0971 0.9388 0.077 Uiso 1 1 calc . . .
C17 C 0.8574(4) 1.01584(12) 1.0253(2) 0.0615(7) Uani 1 1 d . . .
H17 H 0.8119 1.0365 1.0885 0.074 Uiso 1 1 calc . . .
C18 C 0.8661(3) 0.94958(10) 1.02276(18) 0.0466(5) Uani 1 1 d . . .
H18 H 0.8270 0.9253 1.0843 0.056 Uiso 1 1 calc . . .
P1 P 0.78569(6) 0.75909(3) 0.24912(5) 0.03990(16) Uani 1 1 d . . .
F1 F 0.64652(17) 0.78651(7) 0.32552(13) 0.0681(4) Uani 1 1 d . A .
F2 F 0.92221(16) 0.73152(7) 0.17061(12) 0.0624(4) Uani 1 1 d . A .
F3 F 0.6984(6) 0.7891(3) 0.1346(3) 0.0997(17) Uani 0.70 1 d P A 1
F4 F 0.8756(6) 0.7276(3) 0.3540(3) 0.1084(17) Uani 0.70 1 d P A 1
F5 F 0.8826(5) 0.82333(19) 0.2620(5) 0.0958(12) Uani 0.70 1 d P A 1
F6 F 0.6878(7) 0.6956(2) 0.2216(6) 0.119(3) Uani 0.70 1 d P A 1
F3A F 0.7655(14) 0.8164(5) 0.1706(12) 0.115(5) Uani 0.30 1 d P A 2
F4A F 0.7883(10) 0.7013(5) 0.3359(9) 0.090(3) Uani 0.30 1 d P A 2
F5A F 0.9086(9) 0.7953(5) 0.3328(9) 0.097(3) Uani 0.30 1 d P A 2
F6A F 0.6568(13) 0.7217(7) 0.1827(8) 0.107(5) Uani 0.30 1 d P A 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'
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'
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
N1 O1 C5 112.50(15) . . ?
N2 O2 C12 110.77(14) . . ?
C1 N1 O1 122.88(17) . . ?
C1 N1 C2 111.69(17) . . ?
O1 N1 C2 124.74(18) . . ?
C1 N2 O2 122.20(17) . . ?
C1 N2 C3 111.42(17) . . ?
O2 N2 C3 125.99(17) . . ?
N1 C1 N2 104.79(17) . . ?
N1 C1 C4 127.9(2) . . ?
N2 C1 C4 127.3(2) . . ?
C3 C2 N1 106.18(18) . . ?
C2 C3 N2 105.92(17) . . ?
O1 C5 C6 111.52(17) . . ?
C7 C6 C11 118.6(2) . . ?
C7 C6 C5 119.89(19) . . ?
C11 C6 C5 121.46(19) . . ?
C8 C7 C6 120.9(2) . . ?
C7 C8 C9 120.0(2) . . ?
C10 C9 C8 119.6(2) . . ?
C9 C10 C11 120.7(2) . . ?
C10 C11 C6 120.0(2) . . ?
O2 C12 C13 104.97(15) . . ?
C18 C13 C14 119.04(18) . . ?
C18 C13 C12 120.38(19) . . ?
C14 C13 C12 120.5(2) . . ?
C15 C14 C13 120.1(2) . . ?
C16 C15 C14 120.5(2) . . ?
C17 C16 C15 119.5(2) . . ?
C16 C17 C18 120.6(2) . . ?
C17 C18 C13 120.3(2) . . ?
F3A P1 F6A 92.6(7) . . ?
F3A P1 F4 148.1(7) . . ?
F6A P1 F4 119.3(5) . . ?
F3A P1 F5 54.7(6) . . ?
F6A P1 F5 147.3(6) . . ?
F4 P1 F5 93.4(3) . . ?
F3A P1 F4A 173.7(5) . . ?
F6A P1 F4A 85.3(6) . . ?
F5 P1 F4A 127.1(5) . . ?
F3A P1 F5A 92.4(7) . . ?
F6A P1 F5A 172.5(6) . . ?
F4 P1 F5A 55.9(5) . . ?
F4A P1 F5A 89.1(6) . . ?
F3A P1 F6 120.0(7) . . ?
F4 P1 F6 91.7(3) . . ?
F5 P1 F6 173.8(3) . . ?
F4A P1 F6 58.5(4) . . ?
F5A P1 F6 147.5(6) . . ?
F3A P1 F2 90.2(4) . . ?
F6A P1 F2 91.9(5) . . ?
F4 P1 F2 87.90(14) . . ?
F5 P1 F2 89.06(15) . . ?
F4A P1 F2 95.8(3) . . ?
F5A P1 F2 93.6(3) . . ?
F6 P1 F2 87.7(2) . . ?
F3A P1 F1 89.3(4) . . ?
F6A P1 F1 87.1(5) . . ?
F4 P1 F1 93.07(14) . . ?
F5 P1 F1 91.51(15) . . ?
F4A P1 F1 84.7(3) . . ?
F5A P1 F1 87.5(3) . . ?
F6 P1 F1 91.7(2) . . ?
F2 P1 F1 178.84(9) . . ?
F6A P1 F3 59.8(5) . . ?
F4 P1 F3 176.4(2) . . ?
F5 P1 F3 87.6(3) . . ?
F4A P1 F3 145.0(5) . . ?
F5A P1 F3 125.3(5) . . ?
F6 P1 F3 87.1(3) . . ?
F2 P1 F3 88.67(17) . . ?
F1 P1 F3 90.34(17) . . ?
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
O1 N1 1.368(2) . ?
O1 C5 1.479(3) . ?
O2 N2 1.380(2) . ?
O2 C12 1.477(2) . ?
N1 C1 1.316(3) . ?
N1 C2 1.382(3) . ?
N2 C1 1.326(3) . ?
N2 C3 1.384(3) . ?
C1 C4 1.467(3) . ?
C2 C3 1.329(3) . ?
C5 C6 1.491(3) . ?
C6 C7 1.381(3) . ?
C6 C11 1.386(3) . ?
C7 C8 1.374(3) . ?
C8 C9 1.377(4) . ?
C9 C10 1.367(4) . ?
C10 C11 1.380(4) . ?
C12 C13 1.497(3) . ?
C13 C18 1.381(3) . ?
C13 C14 1.385(3) . ?
C14 C15 1.378(3) . ?
C15 C16 1.374(4) . ?
C16 C17 1.369(4) . ?
C17 C18 1.376(3) . ?
P1 F3A 1.498(6) . ?
P1 F6A 1.501(7) . ?
P1 F4 1.535(3) . ?
P1 F5 1.559(3) . ?
P1 F4A 1.561(7) . ?
P1 F5A 1.562(7) . ?
P1 F6 1.571(4) . ?
P1 F2 1.5895(13) . ?
P1 F1 1.5903(13) . ?
P1 F3 1.601(3) . ?
