#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:22:48 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179575 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/40/4504067.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_4504067
loop_
_publ_author_name
'Reichert, W. Matthew'
'Holbrey, John D.'
'Swatloski, Richard P.'
'Gutowski, Keith E.'
'Visser, Ann E.'
'Nieuwenhuyzen, Mark'
'Seddon, Kenneth R.'
'Rogers, Robin D.'
_publ_section_title
;
 Solid-State Analysis of Low-Melting 1,3-Dialkylimidazolium
 Hexafluorophosphate Salts (Ionic Liquids) by Combined X-ray
 Crystallographic and Computational Analyses
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1106
_journal_paper_doi               10.1021/cg060746u
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C8 H15 F6 N2 P'
_chemical_formula_weight         284.19
_chemical_name_common
'1-sec-butyl-3-methylimidazolium hexafluorophosphate'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 116.416(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9541(9)
_cell_length_b                   8.0375(8)
_cell_length_c                   9.6548(9)
_cell_measurement_reflns_used    766
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      21.61
_cell_measurement_theta_min      2.469
_cell_volume                     622.29(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7232
_diffrn_reflns_theta_full        28.58
_diffrn_reflns_theta_max         28.58
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.698544
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             292
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1569
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.253
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1303P)²+0.3671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2147
_refine_ls_wR_factor_ref         0.2261
_reflns_number_gt                1285
_reflns_number_total             1569
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060746usi20061024_064425.cif
_cod_data_source_block           6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               4504067
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
P P -0.23614(14) 0.2500 0.22476(11) 0.0428(4) Uani 1 2 d S
F1A F -0.3936(6) 0.1946(6) 0.2394(7) 0.0907(18) Uani 0.50 1 d P
F1B F -0.0795(10) 0.1713(8) 0.2103(11) 0.121(3) Uani 0.50 1 d P
F2A F -0.3702(17) 0.390(2) 0.1023(18) 0.075(5) Uani 0.33 1 d P
F2B F -0.3055(18) 0.3830(18) 0.0955(14) 0.052(4) Uani 0.33 1 d P
F2C F -0.239(2) 0.372(3) 0.098(2) 0.074(5) Uani 0.33 1 d P
F3A F -0.113(2) 0.123(3) 0.355(3) 0.072(4) Uani 0.33 1 d P
F3B F -0.172(3) 0.123(3) 0.353(2) 0.069(8) Uani 0.33 1 d P
F3C F -0.218(3) 0.110(2) 0.354(2) 0.063(5) Uani 0.33 1 d P
N1 N 0.1935(4) 0.2500 -0.1896(4) 0.0381(7) Uani 1 2 d S
N2 N -0.0574(5) 0.2500 -0.2232(5) 0.0654(13) Uani 1 2 d S
C1 C 0.3372(6) 0.2500 -0.2246(6) 0.0582(12) Uani 1 2 d S
H1A H 0.2979 0.2500 -0.3348 0.087 Uiso 1 2 d SR
H1B H 0.4036 0.3475 -0.1813 0.087 Uiso 1 1 d R
C2 C 0.2000(5) 0.2500 -0.0466(4) 0.0450(10) Uani 1 2 d S
H2A H 0.2980 0.2500 0.0491 0.054 Uiso 1 2 calc SR
C3 C 0.0424(6) 0.2500 -0.0653(5) 0.0537(11) Uani 1 2 d S
H3A H 0.0066 0.2500 0.0137 0.064 Uiso 1 2 calc SR
C4 C 0.0387(5) 0.2500 -0.2940(5) 0.0535(11) Uani 1 2 d S
H4A H 0.0015 0.2500 -0.4027 0.064 Uiso 1 2 calc SR
C5 C -0.2421(9) 0.2500 -0.3071(11) 0.118(3) Uani 1 2 d SDU
H5A H -0.2760 0.2663 -0.4155 0.142 Uiso 0.50 1 d PR
C6 C -0.3326(11) 0.3647(16) -0.3052(16) 0.093(3) Uani 0.50 1 d PDU
H6A H -0.2770 0.3764 -0.1947 0.111 Uiso 0.50 1 d PR
H6B H -0.4505 0.3518 -0.3402 0.111 Uiso 0.50 1 d PR
C7 C -0.2764(10) 0.5220(11) -0.3360(10) 0.0641(19) Uani 0.50 1 d PDU
H7A H -0.3138 0.6266 -0.3150 0.096 Uiso 0.50 1 d PR
H7B H -0.1578 0.5255 -0.3006 0.096 Uiso 0.50 1 d PR
H7C H -0.3304 0.5011 -0.4453 0.096 Uiso 0.50 1 d PR
C8 C -0.2935(11) 0.0506(15) -0.2794(12) 0.066(2) Uani 0.50 1 d PDU
H8A H -0.4131 0.0468 -0.3328 0.099 Uiso 0.50 1 d PR
H8B H -0.2480 -0.0351 -0.3187 0.099 Uiso 0.50 1 d PR
H8C H -0.2577 0.0333 -0.1708 0.099 Uiso 0.50 1 d PR
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_1
_geom_angle_site_symmetry_3
F3B P F3B 85.4(18) 4_565 .
F3B P F1A 98.6(9) 4_565 .
F3B P F1A 76.0(10) . .
F3B P F1A 76.0(10) 4_565 4_565
F3B P F1A 98.6(9) . 4_565
F1A P F1A 33.5(4) . 4_565
F3B P F2B 178.1(10) 4_565 4_565
F3B P F2B 93.6(10) . 4_565
F1A P F2B 79.6(5) . 4_565
F1A P F2B 102.6(6) 4_565 4_565
F3B P F2B 93.6(10) 4_565 .
F3B P F2B 178.1(10) . .
F1A P F2B 102.6(6) . .
F1A P F2B 79.6(5) 4_565 .
F2B P F2B 87.4(11) 4_565 .
F3B P F2C 159.8(11) 4_565 4_565
F3B P F2C 94.9(12) . 4_565
F1A P F2C 101.1(6) . 4_565
F1A P F2C 123.7(7) 4_565 4_565
F2B P F2C 21.9(6) 4_565 4_565
F2B P F2C 86.6(8) . 4_565
F3B P F2C 94.9(12) 4_565 .
F3B P F2C 159.8(11) . .
F1A P F2C 123.7(7) . .
F1A P F2C 101.1(6) 4_565 .
F2B P F2C 86.6(8) 4_565 .
F2B P F2C 21.9(6) . .
F2C P F2C 77.9(15) 4_565 .
F3B P F1B 77.0(9) 4_565 4_565
F3B P F1B 108.2(10) . 4_565
F1A P F1B 173.5(3) . 4_565
F1A P F1B 140.0(3) 4_565 4_565
F2B P F1B 104.8(5) 4_565 4_565
F2B P F1B 73.1(5) . 4_565
F2C P F1B 83.7(6) 4_565 4_565
F2C P F1B 52.7(7) . 4_565
F3B P F1B 108.2(10) 4_565 .
F3B P F1B 77.0(9) . .
F1A P F1B 140.0(3) . .
F1A P F1B 173.5(3) 4_565 .
F2B P F1B 73.1(5) 4_565 .
F2B P F1B 104.8(5) . .
F2C P F1B 52.7(7) 4_565 .
F2C P F1B 83.7(6) . .
F1B P F1B 46.6(5) 4_565 .
F3B P F3A 85.0(8) 4_565 .
F3B P F3A 18.8(15) . .
F1A P F3A 94.6(8) . .
F1A P F3A 116.5(8) 4_565 .
F2B P F3A 94.5(10) 4_565 .
F2B P F3A 162.8(10) . .
F2C P F3A 88.9(12) 4_565 .
F2C P F3A 141.0(10) . .
F1B P F3A 89.9(9) 4_565 .
F1B P F3A 59.8(8) . .
F3B P F3A 18.8(15) 4_565 4_565
F3B P F3A 85.0(8) . 4_565
F1A P F3A 116.5(8) . 4_565
F1A P F3A 94.6(8) 4_565 4_565
F2B P F3A 162.8(10) 4_565 4_565
F2B P F3A 94.5(10) . 4_565
F2C P F3A 141.0(10) 4_565 4_565
F2C P F3A 88.9(12) . 4_565
F1B P F3A 59.8(8) 4_565 4_565
F1B P F3A 89.9(9) . 4_565
F3A P F3A 78.8(18) . 4_565
F1A F1A P 73.23(19) 4_565 .
F1A F1A F2A 115.4(7) 4_565 4_565
P F1A F2A 65.2(5) . 4_565
F1A F1A F3C 115.0(6) 4_565 .
P F1A F3C 62.1(5) . .
F2A F1A F3C 86.5(9) 4_565 .
F1B F1B F2C 104.4(9) 4_565 4_565
F1B F1B P 66.7(3) 4_565 .
F2C F1B P 62.2(7) 4_565 .
F1B F1B F3A 104.1(9) 4_565 .
F2C F1B F3A 95.2(10) 4_565 .
P F1B F3A 60.5(6) . .
F2B F2A F2C 4.0(16) . .
F2B F2A F1A 122(2) . 4_565
F2C F2A F1A 118.3(18) . 4_565
F2B F2A P 66.7(16) . .
F2C F2A P 62.9(14) . .
F1A F2A P 56.3(6) 4_565 .
F2C F2B F2A 172(3) . .
F2C F2B P 80(3) . .
F2A F2B P 92.0(19) . .
F2B F2C F2A 4.1(17) . .
F2B F2C F1B 137(3) . 4_565
F2A F2C F1B 133(2) . 4_565
F2B F2C P 78(3) . .
F2A F2C P 73.9(14) . .
F1B F2C P 65.1(8) 4_565 .
F3B F3A F3C 7(4) . .
F3B F3A F1B 124(5) . .
F3C F3A F1B 126(3) . .
F3B F3A P 69(5) . .
F3C F3A P 74.4(19) . .
F1B F3A P 59.8(10) . .
F3A F3B P 92(6) . .
F3A F3C F1A 129(2) . .
F3A F3C P 72(2) . .
F1A F3C P 56.7(6) . .
C4 N1 C2 109.7(4) . .
C4 N1 C1 124.2(4) . .
C2 N1 C1 126.1(4) . .
C4 N2 C3 108.8(4) . .
C4 N2 C5 123.0(5) . .
C3 N2 C5 128.2(5) . .
N1 C1 H1A 109.2 . .
N1 C1 H1B 109.6 . .
H1A C1 H1B 109.5 . .
C3 C2 N1 107.3(4) . .
C3 C2 H2A 126.4 . .
N1 C2 H2A 126.4 . .
C2 C3 N2 105.9(4) . .
C2 C3 H3A 127.1 . .
N2 C3 H3A 127.1 . .
N1 C4 N2 108.4(4) . .
N1 C4 H4A 125.8 . .
N2 C4 H4A 125.8 . .
C6 C5 C6 96.8(11) . 4_565
C6 C5 N2 124.9(7) . .
C6 C5 N2 124.9(7) 4_565 .
C6 C5 C8 118.1(9) . .
C6 C5 C8 22.8(5) 4_565 .
N2 C5 C8 103.0(4) . .
C6 C5 C8 22.8(5) . 4_565
C6 C5 C8 118.1(9) 4_565 4_565
N2 C5 C8 103.0(4) . 4_565
C8 C5 C8 137.3(9) . 4_565
C6 C5 H5A 91.3 . .
C6 C5 H5A 103.1 4_565 .
N2 C5 H5A 109.3 . .
C8 C5 H5A 108.6 . .
C8 C5 H5A 93.8 4_565 .
C8 C6 C5 117.9(13) 4_565 .
C8 C6 C7 28.8(11) 4_565 .
C5 C6 C7 111.1(7) . .
C8 C6 C6 154.3(12) 4_565 4_565
C5 C6 C6 41.6(6) . 4_565
C7 C6 C6 151.4(6) . 4_565
C8 C6 H5A 115.6 4_565 .
C5 C6 H5A 37.4 . .
C7 C6 H5A 93.1 . .
C6 C6 H5A 60.0 4_565 .
C8 C6 H6A 67.1 4_565 .
C5 C6 H6A 94.0 . .
C7 C6 H6A 95.0 . .
C6 C6 H6A 95.6 4_565 .
H5A C6 H6A 129.3 . .
C8 C6 H6B 119.3 4_565 .
C5 C6 H6B 122.7 . .
C7 C6 H6B 116.9 . .
C6 C6 H6B 83.8 4_565 .
H5A C6 H6B 109.9 . .
H6A C6 H6B 110.4 . .
C8 C7 C6 25.1(10) 4_565 .
C8 C7 H7A 106.4 4_565 .
C6 C7 H7A 122.6 . .
C8 C7 H7B 106.0 4_565 .
C6 C7 H7B 112.7 . .
H7A C7 H7B 109.5 . .
C8 C7 H7C 115.8 4_565 .
C6 C7 H7C 91.3 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C6 C8 C7 126(2) 4_565 4_565
C6 C8 C5 39.3(10) 4_565 .
C7 C8 C5 113.4(10) 4_565 .
C6 C8 H8A 67.0 4_565 .
C7 C8 H8A 96.3 4_565 .
C5 C8 H8A 104.9 . .
C6 C8 H8B 137.1 4_565 .
C7 C8 H8B 14.9 4_565 .
C5 C8 H8B 114.6 . .
H8A C8 H8B 109.5 . .
C6 C8 H8C 111.8 4_565 .
C7 C8 H8C 122.0 4_565 .
C5 C8 H8C 108.8 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P F3B 1.51(2) 4_565
P F3B 1.51(2) .
P F1A 1.543(4) .
P F1A 1.543(4) 4_565
P F2B 1.548(12) 4_565
P F2B 1.548(12) .
P F2C 1.560(19) 4_565
P F2C 1.560(19) .
P F1B 1.601(5) 4_565
P F1B 1.601(5) .
P F3A 1.61(2) .
P F3A 1.61(2) 4_565
F1A F1A 0.890(10) 4_565
F1A F2A 1.582(16) 4_565
F1A F3C 1.62(2) .
F1B F1B 1.265(14) 4_565
F1B F2C 1.40(2) 4_565
F1B F3A 1.60(3) .
F2A F2B 0.614(14) .
F2A F2C 1.200(19) .
F2A F1A 1.582(16) 4_565
F2B F2C 0.589(17) .
F2C F1B 1.40(2) 4_565
F3A F3B 0.52(3) .
F3A F3C 0.93(3) .
N1 C4 1.301(5) .
N1 C2 1.356(5) .
N1 C1 1.469(5) .
N2 C4 1.315(6) .
N2 C3 1.382(6) .
N2 C5 1.483(7) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C2 C3 1.340(6) .
C2 H2A 0.9500 .
C3 H3A 0.9500 .
C4 H4A 0.9500 .
C5 C6 1.233(12) .
C5 C6 1.233(12) 4_565
C5 C8 1.721(11) .
C5 C8 1.721(11) 4_565
C5 H5A 0.9600 .
C6 C8 0.755(13) 4_565
C6 C7 1.440(11) .
C6 C6 1.84(3) 4_565
C6 H5A 1.5800 .
C6 H6A 0.9600 .
C6 H6B 0.9601 .
C7 C8 0.859(12) 4_565
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 C6 0.755(13) 4_565
C8 C7 0.859(12) 4_565
C8 H8A 0.9600 .
C8 H8B 0.9601 .
C8 H8C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7B F1B 0.96 2.24 3.102(11) 149.6 2
C7 H7A H7A 0.96 1.98 2.862(17) 151.2 4_575
C1 H1B F2A 0.96 2.60 3.276(17) 127.3 1_655
C4 H4A F3A 0.95 2.33 3.21(2) 153.0 1_554
C4 H4A F3A 0.95 2.33 3.21(2) 153.0 4_564
C4 H4A F3B 0.95 2.40 3.24(2) 147.3 1_554
C4 H4A F3B 0.95 2.40 3.24(2) 147.3 4_564
C6 H6B C1 0.96 2.72 3.499(10) 138.3 1_455
C3 H3A F1B 0.95 2.43 3.355(7) 164.9 .
C3 H3A F1B 0.95 2.43 3.355(7) 164.9 4_565
C4 H4A F3C 0.95 2.56 3.342(19) 139.9 1_554
C4 H4A F3C 0.95 2.56 3.342(19) 139.9 4_564
C6 H6B H1B 0.96 2.42 3.089(11) 126.7 1_455
C6 H6A F2C 0.96 2.69 3.60(2) 157.7 .
C2 H2A F1A 0.95 2.59 3.482(7) 157.5 1_655
C2 H2A F1A 0.95 2.59 3.482(7) 157.5 4_665
C1 H1B F2B 0.96 2.80 3.483(15) 129.3 1_655
C1 H1B F2B 0.96 2.61 3.264(15) 125.9 3_565
C8 H8C F2C 0.96 2.64 3.51(2) 151.2 4_565
C7 H7A C7 0.96 2.86 3.666(17) 141.9 4_575
C7 H7C F3C 0.96 2.71 3.432(16) 132.8 4_564
C1 H1B F2B 0.96 2.61 3.264(15) 125.9 3_565
C5 H5A F3C 0.96 2.70 3.56(2) 150.2 4_564
C1 H1B F3C 0.96 2.74 3.141(17) 105.8 2
C1 H1B H6B 0.96 2.42 2.723(10) 98.0 1_655
