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_2312711
_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(I3), 4(C2 H6 O S), C18 H26 N2'
_chemical_formula_sum            'C26 H50 I6 N2 O4 S4'
_chemical_formula_weight         1344.32
_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   geom
_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                72.055(2)
_cell_angle_beta                 86.424(3)
_cell_angle_gamma                73.147(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7562(4)
_cell_length_b                   13.3158(3)
_cell_length_c                   18.6498(5)
_cell_measurement_reflns_used    13768
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      32.2100
_cell_measurement_theta_min      3.4140
_cell_volume                     2205.00(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (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      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -40.00  50.00   1.00   12.50    --  -16.94  57.00-180.00   90
  2  \w    -40.00  16.00   1.00   12.50    --  -16.94 -77.00-180.00   56
  3  \w    -51.00   6.00   1.00   12.50    --  -16.94 -57.00  30.00   57
  4  \w    -11.00  56.00   1.00   12.50    --  -16.94  38.00 -60.00   67
  5  \w    -29.00  -3.00   1.00   12.50    --  -16.94 -77.00 -30.00   26
  6  \w   -100.00 -73.00   1.00   12.50    --  -16.94-178.00 -90.00   27
  7  \w    -20.00  57.00   1.00   12.50    --  -16.94  38.00  60.00   77
  8  \w     -3.00  24.00   1.00   12.50    --   18.97 -99.00  60.00   27
  9  \w     40.00 105.00   1.00   12.50    --   18.97 178.00  60.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0460429000
_diffrn_orient_matrix_UB_12      0.0172809000
_diffrn_orient_matrix_UB_13      -0.0291765000
_diffrn_orient_matrix_UB_21      -0.0405341000
_diffrn_orient_matrix_UB_22      -0.0099234000
_diffrn_orient_matrix_UB_23      -0.0260212000
_diffrn_orient_matrix_UB_31      -0.0448647000
_diffrn_orient_matrix_UB_32      0.0549118000
_diffrn_orient_matrix_UB_33      -0.0084391000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26067
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.122
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.445
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.025
_exptl_crystal_description       prism
_exptl_crystal_F_000             1268
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.813
_refine_diff_density_min         -1.505
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         10124
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+2.6003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0852
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7957
_reflns_number_total             10124
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            aw5097sup1.cif
_cod_data_source_block           hmbi_i2
_cod_depositor_comments
'Adding full bibliography for 2312709--2312717.cif.'
_cod_database_code               2312711
_cod_database_fobs_code          2312711
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C18 H26 N2 I3'
_shelx_estimated_absorpt_t_max   0.369
_shelx_estimated_absorpt_t_min   0.283
_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 C(H,H,H,H,H,H) groups
2. Restrained distances
 S4A-C27 = S4-C27
 1.7 with sigma of 0.02
3. Others
 Sof(H27d)=Sof(H27e)=Sof(H27f)=Sof(S4)=Sof(C26)=Sof(H26d)=Sof(H26e)=Sof(H26f)=
 1-FVAR(1)
 Sof(S4A)=Sof(H27a)=Sof(H27b)=Sof(H27c)=Sof(C26A)=Sof(H26a)=Sof(H26b)=
 Sof(H26c)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C16(H16), C6(H6), C3(H3), C15(H15), C13(H13), C5(H5), C12(H12)
4.b Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C17(H17a,H17b,H17c), C9(H9a,H9b,H9c), C19(H19a,H19b,
 H19c), C8(H8a,H8b,H8c), C7(H7a,H7b,H7c), C25(H25a,H25b,H25c), C22(H22a,H22b,
 H22c), C20(H20a,H20b,H20c), C24(H24a,H24b,H24c), C21(H21a,H21b,H21c), C27(H27d,
 H27e,H27f), C27(H27a,H27b,H27c), C23(H23a,H23b,H23c), C26A(H26a,H26b,H26c),
 C26(H26d,H26e,H26f)
;
_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.788