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_2312710
_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(I), C18 H26 N2, 3(H2 O)'
_chemical_formula_sum            'C18 H32 I2 N2 O3'
_chemical_formula_weight         578.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 92.245(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.6407(5)
_cell_length_b                   8.38540(10)
_cell_length_c                   11.0576(2)
_cell_measurement_reflns_used    6740
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.4630
_cell_measurement_theta_min      3.5860
_cell_volume                     2282.99(7)
_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      100.01(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    105.00 153.00   0.50    1.20    --  113.25  15.00 -30.00   96
  2  \w    102.00 165.00   0.50    1.20    --  113.25  61.00  60.00  126
  3  \w     34.00 121.00   0.50    0.30    --   47.38  15.00 -30.00  174
  4  \w    -64.00 -38.00   0.50    1.20    -- -106.00 125.00 -30.00   52
  5  \w   -107.00 -69.00   0.50    1.20    -- -106.00 125.00 -30.00   76
  6  \w   -112.00 -56.00   0.50    1.20    -- -106.00 125.00  60.00  112
  7  \w    -70.00 -34.00   0.50    1.20    -- -106.00  61.00  90.00   72
  8  \w    -60.00 -33.00   0.50    1.20    -- -106.00  61.00 150.00   54
  9  \w    -71.00 -39.00   0.50    1.20    -- -106.00  61.00 -30.00   64
 10  \w    -69.00 -34.00   0.50    1.20    -- -106.00  61.00  60.00   70
 11  \w    -64.00 -38.00   0.50    1.20    -- -106.00  61.00 -60.00   52
 12  \w    -15.00  11.00   0.50    0.30    --  -47.38  15.00 -30.00   52
 13  \w    -60.00 -34.00   0.50    1.20    -- -106.00  61.00 -90.00   52
 14  \w    -71.00 -45.00   0.50    1.20    -- -106.00  61.00-120.00   52
 15  \w    -71.00 -33.00   0.50    1.20    -- -106.00  61.00-180.00   76
 16  \w   -174.00-136.00   0.50    1.20    -- -106.00 -15.00-120.00   76
 17  \w   -121.00 -92.00   0.50    1.20    -- -106.00 -15.00-120.00   58
 18  \w   -159.00 -92.00   0.50    1.20    -- -106.00 -15.00 159.00  134
 19  \w   -107.00 -42.00   0.50    0.30    --  -47.38 -15.00 159.00  130
 20  \w    -21.00   9.00   0.50    0.30    --   47.38 -15.00 159.00   60
 21  \w      0.00  42.00   0.50    0.30    --   47.38 -37.00   0.00   84
 22  \w     44.00  69.00   0.50    1.20    --  113.25 -61.00-150.00   50
 23  \w     43.00  68.00   0.50    1.20    --  113.25 -61.00  30.00   50
 24  \w     42.00  88.00   0.50    1.20    --  113.25 -77.00  90.00   92
 25  \w     78.00 104.00   0.50    1.20    --  113.25 -94.00  30.00   52
 26  \w     78.00 103.00   0.50    1.20    --  113.25 -94.00   0.00   50
 27  \w     43.00 110.00   0.50    1.20    --  113.25-125.00  30.00  134
 28  \w     26.00  76.00   0.50    0.30    --   47.38-125.00-180.00  100
;
_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      0.0608447000
_diffrn_orient_matrix_UB_12      -0.0156319000
_diffrn_orient_matrix_UB_13      0.0354068000
_diffrn_orient_matrix_UB_21      -0.0142453000
_diffrn_orient_matrix_UB_22      -0.0320619000
_diffrn_orient_matrix_UB_23      0.1322158000
_diffrn_orient_matrix_UB_31      -0.0027263000
_diffrn_orient_matrix_UB_32      -0.1802528000
_diffrn_orient_matrix_UB_33      -0.0266498000
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0321
_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       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7879
_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         69.959
_diffrn_reflns_theta_min         3.590
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    21.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44334
_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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_description       prism
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.017
_refine_diff_density_min         -0.983
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2166
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0571P)^2^+6.9331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2072
_reflns_number_total             2166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            aw5097sup1.cif
_cod_data_source_block           hmb_fumar
_cod_depositor_comments
'Adding full bibliography for 2312709--2312717.cif.'
_cod_database_code               2312710
_cod_database_fobs_code          2312710
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C22 H28 O4 N2'
_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. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O1) \\sim Ueq, Uanis(O1A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O1) = Uanis(O1A)
3. Others
 Sof(O1)=Sof(H1a)=Sof(H1b)=1-FVAR(1)
 Sof(O1A)=Sof(H1Aa)=Sof(H1Ab)=FVAR(1)
 Fixed Sof: O2(0.5) H2a(0.5) H2b(0.5)
4.a Free rotating group:
 O1(H1a,H1b), O1A(H1Aa,H1Ab), O2(H2a,H2b)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C2(H2), C3(H3)
4.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C7(H7a,H7b,H7c)
;
_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 2.134
_oxdiff_exptl_absorpt_empirical_full_min 0.436