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_2312713
_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 H2 O4, 6(H2 O), C18 H26 N2'
_chemical_formula_sum            'C22 H40 N2 O10'
_chemical_formula_weight         492.56
_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             2024-07-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.8529(3)
_cell_length_b                   8.38690(10)
_cell_length_c                   11.93900(10)
_cell_measurement_reflns_used    16681
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.5360
_cell_measurement_theta_min      3.5410
_cell_volume                     2488.55(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 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 0.969
_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   -109.00 -59.00   0.50    0.20    --  -47.51 -47.00  36.00  100
  2  \w      3.00  28.00   0.50    0.20    --   47.51-112.00 169.00   50
  3  \w   -167.00-110.00   0.50    0.80    -- -106.00 -47.00  36.00  114
  4  \w    -94.00 -34.00   0.50    0.80    -- -106.00  76.00  16.00  120
  5  \w     63.00 108.00   0.50    0.80    --  113.25-112.00 169.00   90
  6  \w     84.00 110.00   0.50    0.20    --   47.51 125.00-180.00   52
  7  \w     48.00  83.00   0.50    0.20    --   47.51-112.00 169.00   70
  8  \w    -27.00  26.00   0.50    0.20    --   47.51 -19.00-120.00  106
  9  \w    -89.00 -42.00   0.50    0.80    -- -106.00  77.00 -30.00   94
 10  \w   -170.00-140.00   0.50    0.80    -- -106.00 -30.00 -90.00   60
 11  \w   -125.00 -99.00   0.50    0.80    -- -106.00 -30.00 -90.00   52
 12  \w     54.00 106.00   0.50    0.80    --  113.25 -77.00 150.00  104
 13  \w     42.00  67.00   0.50    0.80    --  113.25 -61.00 150.00   50
 14  \w     42.00  67.00   0.50    0.80    --  113.25 -61.00  90.00   50
 15  \w     45.00  70.00   0.50    0.80    --  113.25 -61.00  60.00   50
 16  \w     42.00  67.00   0.50    0.80    --  113.25 -61.00-180.00   50
 17  \w     77.00 102.00   0.50    0.80    --  113.25 -76.00-110.00   50
 18  \w   -119.00 -73.00   0.50    0.20    --  -47.51-125.00 120.00   92
 19  \w    -19.00  21.00   0.50    0.20    --   47.51 -19.00 120.00   80
 20  \w     46.00  95.00   0.50    0.20    --   47.51-125.00 -60.00   98
 21  \w     43.00 119.00   0.50    0.20    --   47.51  57.00-180.00  152
 22  \w     75.00 118.00   0.50    0.20    --   47.51 125.00-120.00   86
 23  \w    -15.00  25.00   0.50    0.20    --   47.51 -19.00 -60.00   80
 24  \w    -14.00  13.00   0.50    0.20    --   47.51 -19.00 -90.00   54
 25  \w    -27.00  -1.00   0.50    0.20    --   47.51 -19.00  90.00   52
 26  \w   -123.00 -92.00   0.50    0.80    -- -106.00 -15.00 120.00   62
 27  \w   -138.00 -85.00   0.50    0.80    -- -106.00-125.00 150.00  106
 28  \w   -177.00 -91.00   0.50    0.80    -- -106.00 -61.00 150.00  172
 29  \w    -66.00 -36.00   0.50    0.80    -- -106.00  61.00  30.00   60
 30  \w    -60.00 -33.00   0.50    0.80    -- -106.00  61.00 150.00   54
 31  \w   -112.00 -75.00   0.50    0.80    -- -106.00 125.00 -60.00   74
 32  \w   -171.00-113.00   0.50    0.80    -- -106.00 -30.00-150.00  116
 33  \w    -70.00 -33.00   0.50    0.80    -- -106.00 125.00 -60.00   74
 34  \w   -155.00 -95.00   0.50    0.80    -- -106.00 -15.00 150.00  120
 35  \w   -173.00-140.00   0.50    0.80    -- -106.00 -30.00  90.00   66
 36  \w   -108.00 -39.00   0.50    0.80    -- -106.00 125.00   0.00  138
 37  \w   -174.00-161.00   0.50    0.80    -- -106.00 -15.00 120.00   26
;
_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      -0.0125741000
_diffrn_orient_matrix_UB_12      -0.1465546000
_diffrn_orient_matrix_UB_13      -0.0733510000
_diffrn_orient_matrix_UB_21      0.0341056000
_diffrn_orient_matrix_UB_22      -0.1050973000
_diffrn_orient_matrix_UB_23      0.0784282000
_diffrn_orient_matrix_UB_31      -0.0502063000
_diffrn_orient_matrix_UB_32      -0.0348648000
_diffrn_orient_matrix_UB_33      0.0715687000
_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  0.0422
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23452
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.663
_diffrn_reflns_theta_min         3.557
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80300
_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             1064
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.870
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0587
_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^)+(0.0848P)^2^+2.6008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1647
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2466
_reflns_number_total             2633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            aw5097sup1.cif
_cod_data_source_block           fumarate0002
_cod_depositor_comments
'Adding full bibliography for 2312709--2312717.cif.'
_cod_database_code               2312713
_cod_database_fobs_code          2312713
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C22 H28 N2 O4'
_shelx_estimated_absorpt_t_max   0.888
_shelx_estimated_absorpt_t_min   0.793
_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.a Free rotating group:
 O5(H5a,H5b), O3(H3a,H3b), O4(H4a,H4b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C2(H2), C11(H11)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c)
;
_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 1.636
_oxdiff_exptl_absorpt_empirical_full_min 0.501