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_2312714
_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         '3(O12 V4), 34(H2 O), 6(C18 H26 N2)'
_chemical_formula_sum            'C108 H224 N12 O70 V12'
_chemical_formula_weight         3422.26
_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             2024-03-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_cell_angle_alpha                92.859(2)
_cell_angle_beta                 94.838(2)
_cell_angle_gamma                101.7990(10)
_cell_formula_units_Z            1
_cell_length_a                   9.07440(10)
_cell_length_b                   17.4077(2)
_cell_length_c                   25.1209(7)
_cell_measurement_reflns_used    30200
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.9260
_cell_measurement_theta_min      3.2240
_cell_volume                     3861.35(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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    -94.00 -69.00   0.50    0.30    --  -47.38 154.00   4.00   50
  2  \w    -91.00 -10.00   0.50    0.30    --  -47.38 120.00-154.00  162
  3  \w   -115.00 -86.00   0.50    0.30    --  -47.38-154.00 -35.00   58
  4  \w     73.00 112.00   0.50    0.30    --   47.38-154.00 -35.00   78
  5  \w     65.00  91.00   0.50    0.30    --   47.38 154.00   4.00   52
  6  \w     10.00  88.00   0.50    0.30    --   47.38-120.00 122.00  156
  7  \w   -102.00 -77.00   0.50    1.60    -- -106.00 154.00   4.00   50
  8  \w   -132.00-107.00   0.50    1.60    -- -106.00-154.00 -35.00   50
  9  \w   -103.00 -70.00   0.50    1.60    -- -106.00 120.00-154.00   66
 10  \w   -152.00-107.00   0.50    1.60    -- -106.00-120.00 122.00   90
 11  \w     54.00 130.00   0.50    1.60    --  113.25 154.00   4.00  152
 12  \w     94.00 131.00   0.50    1.60    --  113.25-154.00 -35.00   74
 13  \w    103.00 128.00   0.50    1.60    --  113.25 120.00-154.00   50
 14  \w     51.00  76.00   0.50    1.60    --  113.25-120.00 122.00   50
 15  \w   -118.00 -73.00   0.50    0.30    --  -47.38-125.00 150.00   90
 16  \w   -107.00 -81.00   0.50    0.30    --  -47.38-125.00-120.00   52
 17  \w    -26.00  15.00   0.50    0.30    --   47.38 -19.00-180.00   82
 18  \w     26.00 120.00   0.50    0.30    --   47.38  77.00-150.00  188
 19  \w     35.00 120.00   0.50    0.30    --   47.38  57.00 -30.00  170
 20  \w     78.00 119.00   0.50    0.30    --   47.38 125.00-120.00   82
 21  \w    -26.00  10.00   0.50    0.30    --   47.38 -19.00 -90.00   72
 22  \w   -177.00 -98.00   0.50    1.60    -- -106.00 -77.00  60.00  158
 23  \w    -67.00 -34.00   0.50    1.60    -- -106.00  61.00  60.00   66
 24  \w   -110.00 -33.00   0.50    1.60    -- -106.00 125.00-120.00  154
 25  \w   -162.00-135.00   0.50    1.60    -- -106.00 -30.00-180.00   54
 26  \w   -108.00 -54.00   0.50    1.60    -- -106.00 109.00 156.19  108
 27  \w   -121.00 -53.00   0.50    1.60    -- -106.00 139.00   2.02  136
 28  \w    -60.00 -33.00   0.50    1.60    -- -106.00  61.00-120.00   54
 29  \w   -108.00 -74.00   0.50    1.60    -- -106.00 112.00 114.23   68
 30  \w   -170.00 -84.00   0.50    1.60    -- -106.00 -77.00-180.00  172
 31  \w   -107.00 -38.00   0.50    1.60    -- -106.00 109.00  80.00  138
 32  \w    -69.00 -33.00   0.50    1.60    -- -106.00 125.00 -30.00   72
 33  \w    -70.00 -44.00   0.50    1.60    -- -106.00 140.00  90.43   52
 34  \w    -68.00 -35.00   0.50    1.60    -- -106.00  61.00-180.00   66
 35  \w   -105.00 -79.00   0.50    1.60    -- -106.00 125.00 -30.00   52
 36  \w   -108.00 -73.00   0.50    1.60    -- -106.00 125.00-180.00   70
 37  \w   -105.00 -33.00   0.50    1.60    -- -106.00 113.00  89.88  144
 38  \w   -122.00 -97.00   0.50    1.60    -- -106.00 -30.00-180.00   50
 39  \w   -119.00 -92.00   0.50    1.60    -- -106.00 135.00  -4.16   54
 40  \w    -62.00 -34.00   0.50    1.60    -- -106.00 125.00-180.00   56
 41  \w    104.00 178.00   0.50    1.60    --  113.25  30.00-150.00  148
 42  \w     97.00 174.00   0.50    1.60    --  113.25  61.00 -90.00  154
 43  \w    102.00 177.00   0.50    1.60    --  113.25  45.00 -30.00  150
 44  \w    102.00 167.00   0.50    1.60    --  113.25  15.00  90.00  130
 45  \w     50.00 103.00   0.50    1.60    --  113.25 -77.00 120.00  106
 46  \w     42.00  71.00   0.50    1.60    --  113.25 -61.00 -60.00   58
 47  \w     42.00  67.00   0.50    1.60    --  113.25 -61.00 -30.00   50
 48  \w    134.00 175.00   0.50    1.60    --  113.25  30.00 -60.00   82
 49  \w    102.00 127.00   0.50    1.60    --  113.25  30.00 -60.00   50
 50  \w     79.00 106.00   0.50    1.60    --  113.25 -94.00 -90.00   54
 51  \w     50.00  94.00   0.50    1.60    --  113.25 -94.00   0.00   88
 52  \w     45.00  81.00   0.50    1.60    --  113.25 -77.00  90.00   72
 53  \w     47.00  77.00   0.50    1.60    --  113.25 -94.00-150.00   60
 54  \w     45.00  70.00   0.50    1.60    --  113.25 -61.00   0.00   50
 55  \w     44.00 106.00   0.50    1.60    --  113.25 -94.00-120.00  124
 56  \w     60.00 106.00   0.50    1.60    --  113.25 -94.00 -30.00   92
 57  \w    105.00 163.00   0.50    1.60    --  113.25  15.00  30.00  116
 58  \w     47.00 102.00   0.50    1.60    --  113.25 -94.00 -60.00  110
 59  \w    117.00 142.00   0.50    1.60    --  113.25  61.00  90.00   50
 60  \w     45.00  70.00   0.50    1.60    --  113.25 -61.00 -90.00   50
;
_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      0.0369552000
_diffrn_orient_matrix_UB_12      0.0328036000
_diffrn_orient_matrix_UB_13      0.0587853000
_diffrn_orient_matrix_UB_21      -0.0021883000
_diffrn_orient_matrix_UB_22      0.0834093000
_diffrn_orient_matrix_UB_23      -0.0174017000
_diffrn_orient_matrix_UB_31      -0.1702726000
_diffrn_orient_matrix_UB_32      -0.0133998000
_diffrn_orient_matrix_UB_33      0.0068771000
_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  0.0559
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            64319
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.000
_diffrn_reflns_theta_min         2.599
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       prism
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         6.930
_refine_diff_density_min         -0.978
_refine_diff_density_rms         0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.480
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1026
_refine_ls_number_reflns         14611
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.495
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.1236
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3152
_refine_ls_wR_factor_ref         0.3227
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12930
_reflns_number_total             14611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            aw5097sup1.cif
_cod_data_source_block           hmbv
_cod_depositor_comments
'Adding full bibliography for 2312709--2312717.cif.'
_cod_database_code               2312714
_cod_database_fobs_code          2312714
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C18 H27 N2 V O4'
_shelx_estimated_absorpt_t_max   0.693
_shelx_estimated_absorpt_t_min   0.418
_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
 O36-H36B = O36-H36A = O21-H21B = O21-H21A
 0.87 with sigma of 0.00001
 H21A-H21B = H36B-H36A
 1.376 with sigma of 0.00001
 O35A-H35C = O35A-H35D = O35-H35B = O35-H35A
 0.87 with sigma of 0.0001
 H35A-H35B = H35D-H35C
 1.376 with sigma of 0.0001
3. Uiso/Uaniso restraints and constraints
Uanis(O36) \\sim Ueq, Uanis(O21) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O13) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O18) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O33) = Uanis(O33A)
Uanis(O34) = Uanis(O34A)
Uanis(O28A) = Uanis(O28)
Uanis(O35A) = Uanis(O35)
4. Others
 Sof(O34A)=Sof(H34C)=Sof(H34D)=1-FVAR(1)
 Sof(O34)=Sof(H34A)=Sof(H34B)=FVAR(1)
 Sof(O35A)=Sof(H35C)=Sof(H35D)=1-FVAR(2)
 Sof(O35)=Sof(H35A)=Sof(H35B)=FVAR(2)
 Sof(O33A)=Sof(H33A)=Sof(H33B)=1-FVAR(3)
 Sof(O33)=Sof(H33C)=Sof(H33D)=FVAR(3)
 Sof(O28A)=Sof(H28D)=Sof(H28E)=1-FVAR(4)
 Sof(O28)=Sof(H28F)=Sof(H28G)=FVAR(4)
 Sof(O21)=Sof(H21A)=Sof(H21B)=1-FVAR(5)
 Sof(O36)=Sof(H36A)=Sof(H36B)=FVAR(5)
5.a Free rotating group:
 O29(H29D,H29E), O30(H30A,H30B), O31(H31A,H31B), O25(H25A,H25B), O23(H23A,
 H23B), O24(H24A,H24B), O22(H22A,H22B), O19(H19D,H19E), O20(H20A,H20B),
 O32(H32A,H32B), O27(H27D,H27E), O26(H26A,H26B), O28A(H28D,H28E), O35(H35A,
 H35B), O34(H34A,H34B), O33A(H33A,H33B), O33(H33C,H33D), O34A(H34C,H34D),
 O35A(H35C,H35D), O28(H28F,H28G)
5.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C6(H6), C26(H26), C36(H36), C23(H23), C45(H45), C25(H25), C46(H46),
 C55(H55), C15(H15), C56(H56), C35(H35), C42(H42), C16(H16), C32(H32), C53(H53),
  C3(H3), C52(H52), C5(H5), C33(H33), C2(H2), C43(H43), C12(H12), C13(H13)
5.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C8(H8A,H8B,H8C), C47(H47A,H47B,H47C), C39(H39A,H39B,
 H39C), C48(H48A,H48B,H48C), C7(H7A,H7B,H7C), C38(H38A,H38B,H38C), C59(H59A,
 H59B,H59C), C17(H17A,H17B,H17C), C37(H37A,H37B,H37C), C58(H58A,H58B,H58C),
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C), C49(H49A,H49B,H49C), C57(H57A,H57B,H57C),
  C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              62561
_shelx_hkl_checksum              25306
_olex2_submission_original_sample_id HMBV
_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 1.992
_oxdiff_exptl_absorpt_empirical_full_min 0.614