Structures of hexamethyl-[1,1'-biphenyl]-4,4'-diammonium salts.
Kanthapazham, Rajakumar; Osipov, Artyom A.; Zherebtsov, Dmitry A.; Efremov, Andrey N.; Nayfert, Sergey A.; Adonin, Sergey A.; Spiridonova, Dar'ya V.; Atapin, Sergey V.; Acta crystallographica Section B, Structural science, crystal engineering and materials 80 (2024) 751–759; doi:10.1107/S2052520624009818

data_2312716
_publ_section_title
;
 Structures of hexamethyl-[1,1'-biphenyl]-4,4'-diammonium salts.
;
_journal_coeditor_code           AW5097
_journal_issue                   6
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_page_first              751
_journal_page_last               759
_journal_paper_doi               10.1107/S2052520624009818
_journal_volume                  80
_journal_year                    2024
_chemical_formula_moiety         'C24 H8 O8, 10(H2 O), 2(C18 H26 N2)'
_chemical_formula_sum            'C60 H80 N4 O18'
_chemical_formula_weight         1145.28
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                92.431(3)
_cell_angle_beta                 90.386(3)
_cell_angle_gamma                113.564(4)
_cell_formula_units_Z            1
_cell_length_a                   10.0218(4)
_cell_length_b                   11.3143(4)
_cell_length_c                   13.6143(4)
_cell_measurement_reflns_used    8305
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.4870
_cell_measurement_theta_min      3.2490
_cell_volume                     1413.25(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_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    -47.00  24.00   0.50   40.00    --  -47.13  52.00-119.00  142
  2  \w   -118.00 -53.00   0.50   40.00    --  -47.13 -52.00  95.00  130
  3  \w    -21.00  28.00   0.50   40.00    --   47.13 -52.00  95.00   98
  4  \w     72.00 100.00   0.50   40.00    --   47.13  52.00-119.00   56
  5  \w   -176.00 -94.00   0.50   40.00    -- -106.00 -52.00  95.00  164
  6  \w    -58.00 -33.00   0.50   40.00    -- -106.00  52.00-119.00   50
  7  \w    101.00 178.00   0.50   40.00    --  113.25  52.00-119.00  154
  8  \w   -119.00 -94.00   0.50   40.00    --  -47.13-125.00  30.00   50
  9  \w    -95.00 -14.00   0.50   40.00    --  -47.13 125.00   0.00  162
 10  \w    -27.00   7.00   0.50   40.00    --   47.13 -19.00 -60.00   68
 11  \w     76.00 119.00   0.50   40.00    --   47.13 125.00  90.00   86
 12  \w      2.00  70.00   0.50   40.00    --   47.13 -77.00-180.00  136
 13  \w      8.00  37.00   0.50   40.00    --   47.13 -37.00  30.00   58
 14  \w    -63.00 -35.00   0.50   40.00    -- -106.00 106.00-124.68   56
 15  \w    -98.00 -47.00   0.50   40.00    -- -106.00  77.00-180.00  102
 16  \w   -170.00 -94.00   0.50   40.00    -- -106.00 -61.00-180.00  152
 17  \w    -71.00 -35.00   0.50   40.00    -- -106.00  61.00-120.00   72
 18  \w   -126.00 -85.00   0.50   40.00    -- -106.00 145.00  57.38   82
 19  \w   -108.00 -33.00   0.50   40.00    -- -106.00 109.00 167.60  150
 20  \w   -107.00 -81.00   0.50   40.00    -- -106.00 106.00-124.68   52
 21  \w   -108.00 -61.00   0.50   40.00    -- -106.00 110.00 -71.01   94
 22  \w   -109.00 -54.00   0.50   40.00    -- -106.00 115.00 -43.04  110
 23  \w    -66.00 -33.00   0.50   40.00    -- -106.00 125.00-120.00   66
 24  \w    -76.00 -50.00   0.50   40.00    -- -106.00 143.00-140.87   52
 25  \w    -83.00 -39.00   0.50   40.00    -- -106.00 125.00   0.00   88
 26  \w   -123.00 -79.00   0.50   40.00    -- -106.00 143.00-140.87   88
 27  \w   -111.00 -64.00   0.50   40.00    -- -106.00 125.00-150.00   94
 28  \w   -101.00 -76.00   0.50   40.00    -- -106.00  77.00  60.00   50
 29  \w    -58.00 -33.00   0.50   40.00    -- -106.00 136.00  -5.57   50
 30  \w   -108.00 -47.00   0.50   40.00    -- -106.00 109.00 110.09  122
 31  \w    -69.00 -43.00   0.50   40.00    -- -106.00 145.00  57.38   52
 32  \w   -120.00 -72.00   0.50   40.00    -- -106.00 136.00  -5.57   96
 33  \w   -112.00 -86.00   0.50   40.00    -- -106.00 125.00   0.00   52
 34  \w    123.00 165.00   0.50   40.00    --  113.25  45.00 150.00   84
 35  \w     52.00 109.00   0.50   40.00    --  113.25-125.00   0.00  114
 36  \w     55.00  95.00   0.50   40.00    --  113.25 -77.00-180.00   80
 37  \w     46.00  79.00   0.50   40.00    --  113.25 -94.00  30.00   66
 38  \w     91.00 173.00   0.50   40.00    --  113.25  77.00  90.00  164
 39  \w    103.00 178.00   0.50   40.00    --  113.25  30.00   0.00  150
 40  \w     61.00 107.00   0.50   40.00    --  113.25-107.00 154.52   92
 41  \w     70.00  95.00   0.50   40.00    --  113.25 -77.00-150.00   50
 42  \w    103.00 169.00   0.50   40.00    --  113.25  30.00  30.00  132
 43  \w     46.00  86.00   0.50   40.00    --  113.25 -77.00 -30.00   80
 44  \w     42.00  67.00   0.50   40.00    --  113.25 -61.00  60.00   50
 45  \w     71.00  97.00   0.50   40.00    --  113.25-125.00 -30.00   52
 46  \w    136.00 161.00   0.50   40.00    --  113.25  45.00 -60.00   50
 47  \w    105.00 133.00   0.50   40.00    --  113.25  45.00 -60.00   56
 48  \w     44.00  69.00   0.50   40.00    --  113.25-125.00 -90.00   50
 49  \w     86.00 111.00   0.50   40.00    --  113.25-125.00 -90.00   50
 50  \w    101.00 161.00   0.50   40.00    --  113.25  45.00-180.00  120
 51  \w    100.00 139.00   0.50   40.00    --  113.25  15.00-180.00   78
 52  \w     46.00 121.00   0.50   40.00    --  113.25-137.00 119.95  150
 53  \w     73.00  99.00   0.50   40.00    --  113.25-125.00 120.00   52
 54  \w     45.00  70.00   0.50   40.00    --  113.25 -61.00   0.00   50
 55  \w     43.00  70.00   0.50   40.00    --  113.25 -61.00-120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1381366000
_diffrn_orient_matrix_UB_12      -0.0932709000
_diffrn_orient_matrix_UB_13      -0.0566426000
_diffrn_orient_matrix_UB_21      0.0831137000
_diffrn_orient_matrix_UB_22      -0.0810398000
_diffrn_orient_matrix_UB_23      -0.0376150000
_diffrn_orient_matrix_UB_31      -0.0464137000
_diffrn_orient_matrix_UB_32      -0.0827820000
_diffrn_orient_matrix_UB_33      0.0906260000
_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  0.0430
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18105
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.000
_diffrn_reflns_theta_min         3.250
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       prism
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5307
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0686
_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^)+(0.1171P)^2^+1.3826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1999
_refine_ls_wR_factor_ref         0.2100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4336
_reflns_number_total             5307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            aw5097sup1.cif
_cod_data_source_block           hmbc-petk
_cod_depositor_comments
'Adding full bibliography for 2312709--2312717.cif.'
_cod_original_cell_volume        1413.25(9)
_cod_database_code               2312716
_cod_database_fobs_code          2312716
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C43 H34 N2 O11 K4'
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.945
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H7e-H6a
 2.5 with sigma of 0.02
3.a Free rotating group:
 O5(H5a,H5b), O7(H7d,H7e), O8(H8d,H8e), O6(H6a,H6b), O9(H9d,H9e)
3.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C22(H22), C23(H23), C6(H6), C28(H28), C29(H29), C5(H5), C2(H2),
 C13(H13), C16(H16), C3(H3), C15(H15)
3.c Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C19(H19a,H19b,H19c), C8(H8a,H8b,H8c), C7(H7a,H7b,H7c),
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c)
;
_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 2.211
_oxdiff_exptl_absorpt_empirical_full_min 0.570