Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-allyl-1H-imidazol-3-ium) bis(hexafluoro phosphate)(V), C10H12F6N2P
Yuan, Kun; Wu, Su-Qin; Nie, Xu-Liang; Xiong, Wan-Ming; Chen, Jing; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 231–233; doi:10.1515/ncrs-2022-0558

data_8107403
_publ_section_title
;
 Crystal structure of
 3,3&#x2032;-(1,4-phenylenebis(methylene))bis(1-allyl-1H-imidazol-3-ium)
 bis(hexafluoro phosphate)(V), C10H12F6N2P
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              231
_journal_page_last               233
_journal_paper_doi               10.1515/ncrs-2022-0558
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C10 H12 N2, F6 P'
_chemical_formula_sum            'C10 H12 F6 N2 P'
_chemical_formula_weight         305.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                66.667(3)
_cell_angle_beta                 74.875(3)
_cell_angle_gamma                74.024(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9854(3)
_cell_length_b                   9.1004(3)
_cell_length_c                   9.2312(3)
_cell_measurement_reflns_used    4627
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0270
_cell_measurement_theta_min      5.1970
_cell_volume                     656.40(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.49a [1]'
_computing_data_collection       'CrysAlisPro 1.171.41.49a [1]'
_computing_data_reduction        'CrysAlisPro 1.171.41.49a [1]'
_computing_molecular_graphics    'Olex2 1.3 [2]'
_computing_publication_material  'Diamond 4.0 [5]'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)[3,4]'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)[3,4]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -119.00 -93.00   0.50    0.05    --  -47.82-171.00 -23.00   52
  2  \w    -78.00 -48.00   0.50    0.05    --  -47.82-171.00 -23.00   60
  3  \w     90.00 118.00   0.50    0.05    --   47.82 171.00  -9.00   56
  4  \w     27.00  89.00   0.50    0.05    --   47.82-114.00 117.00  124
  5  \w    -71.00 -46.00   0.50    0.22    --  -86.25-171.00 -23.00   50
  6  \w   -144.00-119.00   0.50    0.22    --  -86.25-114.00 117.00   50
  7  \w    -55.00 -30.00   0.50    0.22    --  -86.25 114.00-151.00   50
  8  \w    111.00 145.00   0.50    0.22    --  106.49-171.00 -23.00   68
  9  \w     62.00 104.00   0.50    0.22    --  106.49-114.00 117.00   84
 10  \w    104.00 130.00   0.50    0.22    --  106.49 114.00-151.00   52
 11  \w     57.00 108.00   0.50    0.22    --  106.49-171.00 -23.00  102
 12  \w    -25.00  28.00   0.50    0.05    --  -47.82  19.00 120.00  106
 13  \w   -108.00 -77.00   0.50    0.05    --  -47.82-125.00 -90.00   62
 14  \w    -62.00 -33.00   0.50    0.05    --  -47.82 -77.00   0.00   58
 15  \w   -100.00 -75.00   0.50    0.05    --  -47.82-125.00-180.00   50
 16  \w    -71.00 -46.00   0.50    0.05    --  -47.82 114.00-151.00   50
 17  \w   -114.00 -71.00   0.50    0.05    --  -47.82 -77.00   0.00   86
 18  \w    -32.00  -7.00   0.50    0.05    --  -47.82 114.00-151.00   50
 19  \w    -24.00   1.00   0.50    0.05    --   47.82 -19.00-150.00   50
 20  \w    -50.00 -22.00   0.50    0.22    --  -86.25  45.00 -30.00   56
 21  \w   -147.00 -98.00   0.50    0.22    --  -86.25 -30.00 120.00   98
 22  \w   -155.00 -74.00   0.50    0.22    --  -86.25 -45.00-180.00  162
 23  \w    -44.00 -18.00   0.50    0.22    --  -86.25  45.00  90.00   52
 24  \w     37.00  83.00   0.50    0.22    --  106.49 -77.00 150.00   92
 25  \w     43.00  73.00   0.50    0.22    --  106.49 -94.00-150.00   60
 26  \w     35.00  67.00   0.50    0.22    --  106.49 -61.00   0.00   64
 27  \w     79.00 109.00   0.50    0.22    --  106.49-125.00  90.00   60
 28  \w     34.00  69.00   0.50    0.22    --  106.49-125.00  90.00   70
 29  \w     35.00  60.00   0.50    0.22    --  106.49 -61.00  90.00   50
 30  \w     84.00 109.00   0.50    0.22    --  106.49 171.00  -9.00   50
 31  \w     85.00 111.00   0.50    0.22    --  106.49-125.00  60.00   52
 32  \w     40.00 111.00   0.50    0.22    --  106.49-125.00 -90.00  142
 33  \w     96.00 177.00   0.50    0.22    --  106.49  45.00   0.00  162
 34  \w    112.00 138.00   0.50    0.22    --  106.49  30.00 -30.00   52
 35  \w    142.00 177.00   0.50    0.22    --  106.49  30.00 -30.00   70
 36  \w     99.00 139.00   0.50    0.22    --  106.49 125.00-150.00   80
 37  \w    152.00 178.00   0.50    0.22    --  106.49 125.00-150.00   52
 38  \w     35.00  93.00   0.50    0.22    --  106.49-125.00-180.00  116
 39  \w     50.00  92.00   0.50    0.22    --  106.49 -94.00 -30.00   84
 40  \w     59.00 100.00   0.50    0.22    --  106.49 -94.00 -60.00   82
 41  \w     37.00  62.00   0.50    0.22    --  106.49 -94.00  30.00   50
 42  \w     80.00 105.00   0.50    0.22    --  106.49 -94.00  30.00   50
 43  \w     97.00 171.00   0.50    0.22    --  106.49 125.00  60.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1708059000
_diffrn_orient_matrix_UB_12      -0.0911951000
_diffrn_orient_matrix_UB_13      -0.0281441000
_diffrn_orient_matrix_UB_21      -0.0515680000
_diffrn_orient_matrix_UB_22      -0.0938720000
_diffrn_orient_matrix_UB_23      -0.0794215000
_diffrn_orient_matrix_UB_31      0.0306837000
_diffrn_orient_matrix_UB_32      0.1348675000
_diffrn_orient_matrix_UB_33      -0.1641376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7414
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.545
_diffrn_reflns_theta_min         5.198
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.474
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.49a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_description       block
_exptl_crystal_F_000             310
_exptl_crystal_preparation       .
_exptl_crystal_recrystallization_method .
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0068(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)[3,4]'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2601
_refine_ls_number_restraints     187
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0747P)^2^+0.1471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1515
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2224
_reflns_number_total             2765
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0558_suppl.cif
_cod_data_source_block           z-2-1027
_cod_database_code               8107403
_shelx_estimated_absorpt_t_max   0.790
_shelx_estimated_absorpt_t_min   0.612
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F5-F4 \\sim F5-F2 \\sim F5-F3 \\sim F5-F1 \\sim F6-F4 \\sim F6-F2 \\sim F6-F3
\\sim F6-F1 \\sim F4-F2 \\sim F4-F3
 \\sim F2-F1 \\sim F3-F1
 with sigma of 0.04
 P1-F5 \\sim P1-F6 \\sim P1-F4 \\sim P1-F2 \\sim P1-F3 \\sim P1-F1
 with sigma of 0.02
 P1-F1 \\sim P1-F1A
 with sigma of 0.02
 P1-F2 \\sim P1-F2A
 with sigma of 0.02
 P1-F3 \\sim P1-F3A
 with sigma of 0.02
 P1-F4 \\sim P1-F4A
 with sigma of 0.02
 P1-F5 \\sim P1-F5A
 with sigma of 0.02
 P1-F6 \\sim P1-F6A
 with sigma of 0.02
 F2A-F4A \\sim F2A-F1A \\sim F2A-F5A \\sim F2A-F6A \\sim F4A-F6A \\sim F4A-F3A
\\sim F1A-F5A \\sim F1A-F6A
 \\sim F1A-F3A \\sim F5A-F3A \\sim F6A-F3A
 with sigma of 0.04
 P1-F2A \\sim P1-F4A \\sim P1-F1A \\sim P1-F5A \\sim P1-F6A \\sim P1-F3A
 with sigma of 0.02
3. Others
 Sof(F2A)=Sof(F4A)=Sof(F6A)=Sof(F3A)=Sof(F1A)=Sof(F5A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10)
4.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_shelx_res_checksum              45345
_shelx_hkl_checksum              64261
_olex2_exptl_crystal_mounting_method .
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.468
_oxdiff_exptl_absorpt_empirical_full_min 0.731