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_2312712
_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         'C4 H4 O4, 6(H2 O), C18 H26 N2'
_chemical_formula_sum            'C22 H42 N2 O10'
_chemical_formula_weight         494.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-22
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.1134(3)
_cell_length_b                   8.38700(10)
_cell_length_c                   11.8570(2)
_cell_measurement_reflns_used    12259
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.9090
_cell_measurement_theta_min      3.5400
_cell_volume                     2497.39(6)
_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      100.01(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    -66.00  14.00   0.50    0.25    --  -47.51  67.00 116.00  160
  2  \w    -84.00 -33.00   0.50    1.00    -- -106.00  71.00 -13.00  102
  3  \w     45.00 131.00   0.50    1.00    --  113.25 -84.00 106.00  172
  4  \w    103.00 170.00   0.50    1.00    --  113.25  67.00 116.00  134
  5  \w     76.00 102.00   0.50    0.25    --   47.51 125.00  90.00   52
  6  \w     90.00 115.00   0.50    0.25    --   47.51 125.00  30.00   50
  7  \w     74.00 120.00   0.50    0.25    --   47.51 125.00  60.00   92
  8  \w    -59.00 -33.00   0.50    1.00    -- -106.00  61.00  60.00   52
  9  \w    -71.00 -41.00   0.50    1.00    -- -106.00  61.00-150.00   60
 10  \w    -71.00 -45.00   0.50    1.00    -- -106.00  61.00-180.00   52
 11  \w    -66.00 -33.00   0.50    1.00    -- -106.00  61.00 150.00   66
 12  \w    -71.00 -46.00   0.50    1.00    -- -106.00  61.00 -60.00   50
 13  \w     60.00 106.00   0.50    1.00    --  113.25 -77.00-150.00   92
 14  \w     45.00  71.00   0.50    1.00    --  113.25 -61.00 120.00   52
 15  \w     42.00  67.00   0.50    1.00    --  113.25 -61.00   0.00   50
 16  \w     44.00  69.00   0.50    1.00    --  113.25 -61.00 -90.00   50
 17  \w     42.00  67.00   0.50    1.00    --  113.25 -61.00-120.00   50
 18  \w   -172.00-146.00   0.50    1.00    -- -106.00 -84.00 106.00   52
 19  \w   -107.00 -81.00   0.50    0.25    --  -47.51-125.00  90.00   52
 20  \w    -22.00  23.00   0.50    0.25    --  -47.51  19.00-120.00   90
 21  \w    -21.00   5.00   0.50    0.25    --   47.51 -19.00 -60.00   52
 22  \w   -135.00-106.00   0.50    1.00    -- -106.00 -30.00 -90.00   58
 23  \w   -177.00-146.00   0.50    1.00    -- -106.00 -30.00 -90.00   62
 24  \w   -104.00 -78.00   0.50    1.00    -- -106.00  77.00  60.00   52
 25  \w   -128.00 -88.00   0.50    1.00    -- -106.00 -84.00 106.00   80
 26  \w    -62.00 -33.00   0.50    1.00    -- -106.00  77.00  60.00   58
 27  \w     42.00  67.00   0.50    1.00    --  113.25 -61.00  60.00   50
 28  \w     45.00  71.00   0.50    1.00    --  113.25 -61.00  30.00   52
 29  \w    108.00 144.00   0.50    1.00    --  113.25  30.00-180.00   72
 30  \w     71.00 102.00   0.50    1.00    --  113.25-125.00   0.00   62
 31  \w     46.00  72.00   0.50    1.00    --  113.25-125.00-120.00   52
 32  \w     42.00  68.00   0.50    1.00    --  113.25 -61.00 -60.00   52
 33  \w     42.00  84.00   0.50    1.00    --  113.25 -77.00-180.00   84
 34  \w    147.00 173.00   0.50    1.00    --  113.25  30.00-180.00   52
;
_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      -0.0090104000
_diffrn_orient_matrix_UB_12      -0.0907494000
_diffrn_orient_matrix_UB_13      0.1113828000
_diffrn_orient_matrix_UB_21      0.0479029000
_diffrn_orient_matrix_UB_22      -0.1083737000
_diffrn_orient_matrix_UB_23      -0.0267510000
_diffrn_orient_matrix_UB_31      0.0372277000
_diffrn_orient_matrix_UB_32      0.1173378000
_diffrn_orient_matrix_UB_33      0.0613299000
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17634
_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         69.993
_diffrn_reflns_theta_min         3.520
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75142
_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    1.315
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0722P)^2^+2.1081P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1407
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2191
_reflns_number_total             2369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            aw5097sup1.cif
_cod_data_source_block           hmb_yant
_cod_depositor_comments
'Adding full bibliography for 2312709--2312717.cif.'
_cod_database_code               2312712
_cod_database_fobs_code          2312712
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H30 N2 O4'
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.889
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B), O4(H4A,H4B), O6(H6A,H6B)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C3(H3)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              45789
_shelx_hkl_checksum              79266
_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 1.475
_oxdiff_exptl_absorpt_empirical_full_min 0.674