#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/40/4504070.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_4504070
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            'C14 H27 F6 N2 P'
_chemical_formula_weight         368.35
_chemical_name_common
'1-decyl-3-methylimidazolium hexafluorophosphate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 99.3390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.4684(14)
_cell_length_b                   9.8087(6)
_cell_length_c                   9.3107(6)
_cell_measurement_temperature    173(2)
_cell_volume                     1844.5(2)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_method       'ω 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  0.0714
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7815
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       frag
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0015(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.052
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0442P)²+1.0637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                2297
_reflns_number_total             2629
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060746usi20061024_064425.cif
_cod_data_source_block           10
_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)/c
_cod_database_code               4504070
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
P P 0.35455(3) 0.51749(7) 0.27544(7) 0.0433(2) Uani 1 1 d
F1 F 0.41644(10) 0.5782(2) 0.38217(19) 0.0942(7) Uani 1 1 d
F2 F 0.36599(12) 0.62173(18) 0.1515(2) 0.0891(7) Uani 1 1 d
F3 F 0.30665(11) 0.61991(18) 0.3369(2) 0.0811(6) Uani 1 1 d
F4 F 0.40333(8) 0.41176(19) 0.21437(16) 0.0647(5) Uani 1 1 d
F5 F 0.29458(8) 0.45317(18) 0.16743(17) 0.0620(5) Uani 1 1 d
F6 F 0.34369(8) 0.41112(16) 0.39782(16) 0.0590(5) Uani 1 1 d
N1 N 0.34201(10) 0.00298(19) 0.3036(2) 0.0377(5) Uani 1 1 d
N3 N 0.43210(10) 0.1172(2) 0.3684(2) 0.0406(5) Uani 1 1 d
C2 C 0.37069(13) 0.0993(3) 0.3905(3) 0.0400(6) Uani 1 1 d
H2A H 0.3501(12) 0.143(3) 0.453(3) 0.041(7) Uiso 1 1 d
C4 C 0.44279(15) 0.0288(3) 0.2599(3) 0.0526(7) Uani 1 1 d
H4A H 0.4825(15) 0.027(3) 0.231(3) 0.064(9) Uiso 1 1 d
C5 C 0.38729(14) -0.0415(3) 0.2202(3) 0.0508(7) Uani 1 1 d
H5A H 0.3775(15) -0.111(3) 0.156(3) 0.067(9) Uiso 1 1 d
C6 C 0.48048(17) 0.2121(4) 0.4475(4) 0.0586(8) Uani 1 1 d
H6A H 0.461(2) 0.268(5) 0.500(5) 0.14(2) Uiso 1 1 d
H6B H 0.502(2) 0.265(5) 0.387(5) 0.114(15) Uiso 1 1 d
H6C H 0.519(2) 0.172(4) 0.487(4) 0.106(14) Uiso 1 1 d
C7 C 0.27386(13) -0.0474(3) 0.2961(3) 0.0452(6) Uani 1 1 d
H7A H 0.2554(13) -0.003(3) 0.378(3) 0.051(7) Uiso 1 1 d
H7B H 0.2784(13) -0.142(3) 0.308(3) 0.052(8) Uiso 1 1 d
C8 C 0.23128(14) -0.0151(3) 0.1508(3) 0.0431(6) Uani 1 1 d
H8A H 0.1869(13) -0.065(3) 0.145(3) 0.046(7) Uiso 1 1 d
H8B H 0.2516(12) -0.053(3) 0.072(3) 0.044(7) Uiso 1 1 d
C9 C 0.21949(15) 0.1350(3) 0.1266(3) 0.0469(6) Uani 1 1 d
H9A H 0.2631(14) 0.181(3) 0.139(3) 0.055(8) Uiso 1 1 d
H9B H 0.1954(14) 0.168(3) 0.197(3) 0.060(8) Uiso 1 1 d
C10 C 0.18015(14) 0.1708(3) -0.0228(3) 0.0488(7) Uani 1 1 d
H10A H 0.2068(14) 0.139(3) -0.097(3) 0.065(9) Uiso 1 1 d
H10B H 0.1772(15) 0.276(4) -0.029(3) 0.071(9) Uiso 1 1 d
C11 C 0.11151(14) 0.1092(3) -0.0562(3) 0.0492(7) Uani 1 1 d
H11A H 0.0864(15) 0.127(3) 0.015(3) 0.063(9) Uiso 1 1 d
H11B H 0.1166(14) 0.009(3) -0.062(3) 0.067(9) Uiso 1 1 d
C12 C 0.07137(14) 0.1601(3) -0.1987(3) 0.0475(6) Uani 1 1 d
H12A H 0.0972(14) 0.144(3) -0.277(3) 0.055(8) Uiso 1 1 d
H12B H 0.0656(15) 0.261(4) -0.198(3) 0.072(9) Uiso 1 1 d
C13 C 0.00419(15) 0.0954(4) -0.2405(3) 0.0562(7) Uani 1 1 d
H13A H -0.0207(17) 0.102(4) -0.164(4) 0.087(11) Uiso 1 1 d
H13B H 0.0104(15) -0.006(4) -0.254(3) 0.073(10) Uiso 1 1 d
C14 C -0.03501(14) 0.1492(3) -0.3813(3) 0.0507(7) Uani 1 1 d
H14A H -0.0081(16) 0.141(3) -0.457(3) 0.073(9) Uiso 1 1 d
H14B H -0.0420(19) 0.244(5) -0.372(4) 0.108(13) Uiso 1 1 d
C15 C -0.10052(16) 0.0817(4) -0.4302(4) 0.0701(10) Uani 1 1 d
H15A H -0.123(2) 0.068(5) -0.365(5) 0.131(18) Uiso 1 1 d
H15B H -0.092(2) -0.025(5) -0.457(5) 0.134(17) Uiso 1 1 d
C16 C -0.1387(2) 0.1369(5) -0.5699(6) 0.0833(12) Uani 1 1 d
H16A H -0.179(2) 0.095(4) -0.598(4) 0.107(13) Uiso 1 1 d
H16B H -0.112(3) 0.140(6) -0.648(6) 0.17(3) Uiso 1 1 d
H16C H -0.151(3) 0.218(7) -0.552(7) 0.18(3) Uiso 1 1 d
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
F3 P F5 91.20(11)
F3 P F6 89.45(9)
F5 P F6 90.55(9)
F3 P F2 91.58(11)
F5 P F2 89.17(11)
F6 P F2 178.94(10)
F3 P F1 90.79(12)
F5 P F1 178.01(11)
F6 P F1 89.30(11)
F2 P F1 90.95(12)
F3 P F4 179.29(10)
F5 P F4 88.87(9)
F6 P F4 89.84(9)
F2 P F4 89.13(10)
F1 P F4 89.15(11)
C2 N1 C5 107.5(2)
C2 N1 C7 126.5(2)
C5 N1 C7 126.0(2)
C2 N3 C4 107.5(2)
C2 N3 C6 126.1(3)
C4 N3 C6 126.4(3)
N3 C2 N1 109.9(2)
C5 C4 N3 107.5(2)
C4 C5 N1 107.6(3)
N1 C7 C8 112.0(2)
C9 C8 C7 113.1(2)
C8 C9 C10 114.1(2)
C11 C10 C9 115.4(2)
C10 C11 C12 113.4(2)
C13 C12 C11 115.2(2)
C12 C13 C14 114.1(3)
C15 C14 C13 115.5(3)
C14 C15 C16 114.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P F3 1.5749(18)
P F5 1.5859(17)
P F6 1.5869(15)
P F2 1.5876(17)
P F1 1.5933(18)
P F4 1.6063(16)
N1 C2 1.318(3)
N1 C5 1.374(3)
N1 C7 1.471(3)
N3 C2 1.318(3)
N3 C4 1.375(3)
N3 C6 1.467(4)
C4 C5 1.329(4)
C7 C8 1.519(4)
C8 C9 1.503(4)
C9 C10 1.531(4)
C10 C11 1.514(4)
C11 C12 1.527(4)
C12 C13 1.507(4)
C13 C14 1.517(4)
C14 C15 1.498(4)
C15 C16 1.506(5)
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
C2 H2A F4 0.88(3) 2.56(2) 2.982(3) 110.4(19) 4_566
C2 H2A F5 0.88(3) 2.63(2) 3.262(3) 129(2) 4_566
C2 H2A F6 0.88(3) 2.68(2) 3.111(3) 111.6(18) .
C4 H4A F1 0.90(3) 2.52(3) 3.395(4) 165(3) 2_645
C4 H4A F4 0.90(3) 2.57(3) 3.324(3) 142(2) 2_645
C5 H5A F1 0.91(3) 2.81(3) 3.316(3) 117(2) 4_565
C5 H5A F2 0.91(3) 2.64(3) 3.380(4) 140(2) 1_545
C6 H6A F6 0.88(5) 2.81(5) 3.383(4) 125(4) .
C6 H6B F1 0.93(5) 2.93(4) 3.180(4) 97(3) 3_666
C6 H6C F2 0.90(4) 2.91(4) 3.528(5) 127(3) 2_645
C6 H6B F1 0.93(5) 2.93(4) 3.180(4) 97(3) 3_666
C6 H6B F4 0.93(5) 2.77(4) 3.151(4) 106(3) .
C7 H7A F5 1.01(3) 2.73(3) 3.537(3) 137.8(19) 4_566
C7 H7B F3 0.94(3) 2.41(3) 3.341(3) 172(2) 1_545
C8 H8B F3 0.98(3) 2.70(3) 3.666(3) 172(2) 4_565
C9 H9A F5 0.99(3) 2.75(3) 3.472(3) 130.2(19) .
C10 H10A F6 1.00(3) 2.85(3) 3.633(3) 136(2) 4_565
C16 H16A F5 0.93(5) 2.72(5) 3.649(5) 175(3) 2_544
C8 H8A H16C 1.02(3) 2.37(7) 3.14(7) 132(2) 2_544
C16 H16C H8A 0.86(7) 2.37(7) 3.13(3) 148(5) 2_554
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
N1 C7 C8 C9 -66.4(3)
C7 C8 C9 C10 176.5(2)
C8 C9 C10 C11 59.9(4)
C9 C10 C11 C12 173.6(3)
C10 C11 C12 C13 176.6(3)
C11 C12 C13 C14 179.2(3)
C12 C13 C14 C15 176.9(3)
C13 C14 C15 C16 179.8(4)
C2 N1 C7 C8 114.4(3)
C5 N1 C7 C8 -65.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8220090
2 PubChem 10044526
