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_2312715
_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         '2(C8 H5 O4), C18 H26 N2, 6(H2 O)'
_chemical_formula_sum            'C34 H48 N2 O14'
_chemical_formula_weight         708.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.836(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.9176(2)
_cell_length_b                   8.8157(2)
_cell_length_c                   15.5173(2)
_cell_measurement_reflns_used    10931
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.4600
_cell_measurement_theta_min      3.4460
_cell_volume                     1741.10(5)
_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 2018/3 (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 1.000
_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     85.00 112.00   0.50    0.15    --   47.38 125.00-120.00   54
  2  \w     77.00 104.00   0.50    0.15    --   47.38 125.00 -30.00   54
  3  \w     75.00 110.00   0.50    0.15    --   47.38 125.00   0.00   70
  4  \w     75.00 119.00   0.50    0.15    --   47.38 125.00  60.00   88
  5  \w     74.00 119.00   0.50    0.15    --   47.38 125.00  90.00   90
  6  \w    113.00 176.00   0.50    0.80    --  113.25  15.00-120.00  126
  7  \w     43.00  71.00   0.50    0.80    --  113.25 -61.00-180.00   56
  8  \w     44.00  69.00   0.50    0.80    --  113.25 -61.00-120.00   50
  9  \w     44.00  71.00   0.50    0.80    --  113.25 -61.00 -60.00   54
 10  \w     48.00 100.00   0.50    0.80    --  113.25 -77.00  30.00  104
 11  \w     42.00  67.00   0.50    0.80    --  113.25 -61.00  30.00   50
 12  \w     42.00  67.00   0.50    0.80    --  113.25 -61.00  60.00   50
 13  \w     42.00  67.00   0.50    0.80    --  113.25 -61.00  90.00   50
 14  \w     43.00  70.00   0.50    0.80    --  113.25 -61.00 120.00   54
 15  \w     84.00 170.00   0.50    0.80    --  113.25 105.00 145.00  172
 16  \w     43.00  68.00   0.50    0.80    --  113.25 -61.00-150.00   50
 17  \w    -64.00 -36.00   0.50    0.80    -- -106.00  61.00 -30.00   56
 18  \w   -103.00 -77.00   0.50    0.80    -- -106.00  77.00 -90.00   52
 19  \w    -64.00 -38.00   0.50    0.80    -- -106.00  77.00-180.00   52
 20  \w   -106.00 -80.00   0.50    0.80    -- -106.00  77.00-180.00   52
 21  \w    -58.00 -33.00   0.50    0.80    -- -106.00  77.00 -90.00   50
 22  \w    -69.00 -35.00   0.50    0.80    -- -106.00  61.00 -90.00   68
 23  \w    -58.00 -33.00   0.50    0.80    -- -106.00  61.00   0.00   50
 24  \w     69.00 106.00   0.50    0.80    --  113.25-105.00  44.00   74
 25  \w      1.00  70.00   0.50    0.15    --   47.38-105.00  44.00  138
 26  \w    -71.00 -46.00   0.50    0.80    -- -106.00  61.00 150.00   50
 27  \w   -105.00 -55.00   0.50    0.80    -- -106.00 105.00 145.00  100
 28  \w   -110.00 -75.00   0.50    0.80    -- -106.00 125.00  60.00   70
 29  \w    -70.00 -38.00   0.50    0.80    -- -106.00 125.00  60.00   64
 30  \w    -74.00 -10.00   0.50    0.15    --  -47.38 105.00 145.00  128
 31  \w   -176.00-118.00   0.50    0.80    -- -106.00 -30.00  60.00  116
 32  \w   -172.00-146.00   0.50    0.80    -- -106.00 -77.00  90.00   52
 33  \w   -117.00 -91.00   0.50    0.80    -- -106.00-105.00  44.00   52
 34  \w   -117.00 -86.00   0.50    0.80    -- -106.00 -77.00  90.00   62
 35  \w   -108.00 -73.00   0.50    0.15    --  -47.38-125.00 120.00   70
;
_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      0.1196620000
_diffrn_orient_matrix_UB_12      0.0134193000
_diffrn_orient_matrix_UB_13      0.0041315000
_diffrn_orient_matrix_UB_21      0.0047946000
_diffrn_orient_matrix_UB_22      -0.1682549000
_diffrn_orient_matrix_UB_23      -0.0259670000
_diffrn_orient_matrix_UB_31      -0.0176162000
_diffrn_orient_matrix_UB_32      0.0453154000
_diffrn_orient_matrix_UB_33      -0.0972549000
_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  0.0267
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13802
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.977
_diffrn_reflns_theta_min         3.473
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.883
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85535
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       prism
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.00108(19)
_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)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0399P)^2^+0.5555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3075
_reflns_number_total             3298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            aw5097sup1.cif
_cod_data_source_block           tahmbc
_cod_depositor_comments
'Adding full bibliography for 2312709--2312717.cif.'
_cod_database_code               2312715
_cod_database_fobs_code          2312715
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C27 H28 O7 N2'
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.857
_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) groups, All O(H,H) groups
2. Others
 Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=
 Sof(H13A)=1-FVAR(1)
 Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=FVAR(1)
3.a Free rotating group:
 O7(H7A,H7B), O6(H6A,H6B), O5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3), C6(H6), C12(H12), C13(H13), C15(H15), C16A(H16A),
 C16(H16), C15A(H15A), C12A(H12A), C13A(H13A)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              63388
_shelx_hkl_checksum              12790
_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 1.302
_oxdiff_exptl_absorpt_empirical_full_min 0.762