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_2312717
_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         'C36 H24 Na2 O16, C18 H26 N2, 2(H2 O)'
_chemical_formula_sum            'C54 H54 N2 Na2 O18'
_chemical_formula_weight         1064.97
_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_Hall           'P -4 2n'
_space_group_name_H-M_alt        'P -4 21 c'
_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            8
_cell_length_a                   17.13140(10)
_cell_length_b                   17.13140(10)
_cell_length_c                   35.1640(2)
_cell_measurement_reflns_used    33259
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.1880
_cell_measurement_theta_min      2.5250
_cell_volume                     10320.10(10)
_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 0.990
_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    -25.00   5.00   0.50   10.00    --  -47.38   8.00  23.00   60
  2  \w    -99.00 -19.00   0.50   10.00    --  -47.38 135.00-118.00  160
  3  \w   -101.00 -35.00   0.50   38.00    -- -106.00 135.00-118.00  132
  4  \w   -125.00 -33.00   0.50   38.00    -- -106.00 151.00 -39.00  184
  5  \w     74.00 102.00   0.50   10.00    --   47.38 125.00  30.00   56
  6  \w     95.00 120.00   0.50   10.00    --   47.38 125.00-180.00   50
  7  \w   -161.00-101.00   0.50   38.00    -- -106.00 -15.00  60.00  120
  8  \w     44.00  70.00   0.50   38.00    --  113.25 -61.00  30.00   52
  9  \w     44.00  70.00   0.50   38.00    --  113.25 -61.00 -30.00   52
 10  \w    102.00 171.00   0.50   38.00    --  113.25  15.00 -90.00  138
 11  \w     43.00  70.00   0.50   38.00    --  113.25 -61.00  60.00   54
 12  \w     43.00  69.00   0.50   38.00    --  113.25 -61.00-150.00   52
 13  \w     60.00 113.00   0.50   38.00    --  113.25-133.00  -4.00  106
 14  \w   -112.00 -74.00   0.50   10.00    --  -47.38-125.00 -30.00   76
 15  \w     74.00  99.00   0.50   10.00    --   47.38 125.00   0.00   50
 16  \w    -11.00  18.00   0.50   10.00    --   47.38 -19.00 150.00   58
 17  \w    -18.00  25.00   0.50   10.00    --   47.38 -19.00  60.00   86
 18  \w    -68.00 -33.00   0.50   38.00    -- -106.00  61.00  90.00   70
 19  \w   -112.00 -86.00   0.50   38.00    -- -106.00 -94.00-120.00   52
 20  \w   -171.00-133.00   0.50   38.00    -- -106.00 -94.00-120.00   76
 21  \w     42.00  67.00   0.50   38.00    --  113.25 -61.00   0.00   50
 22  \w    106.00 152.00   0.50   38.00    --  113.25  45.00  90.00   92
 23  \w     42.00  71.00   0.50   38.00    --  113.25 -61.00 150.00   58
 24  \w    119.00 160.00   0.50   38.00    --  113.25  15.00-120.00   82
 25  \w     42.00  67.00   0.50   38.00    --  113.25 -61.00-180.00   50
 26  \w    106.00 141.00   0.50   38.00    --  113.25  45.00-180.00   70
 27  \w    147.00 173.00   0.50   38.00    --  113.25  45.00-180.00   52
 28  \w    117.00 178.00   0.50   38.00    --  113.25  45.00 -90.00  122
 29  \w     42.00  54.50   0.50   38.00    --  113.25-125.00-180.00   25
;
_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      0.0043003000
_diffrn_orient_matrix_UB_12      0.0786553000
_diffrn_orient_matrix_UB_13      0.0211309000
_diffrn_orient_matrix_UB_21      -0.0084899000
_diffrn_orient_matrix_UB_22      0.0436239000
_diffrn_orient_matrix_UB_23      -0.0381010000
_diffrn_orient_matrix_UB_31      -0.0893935000
_diffrn_orient_matrix_UB_32      -0.0003534000
_diffrn_orient_matrix_UB_33      0.0046512000
_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  0.0603
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            74078
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.199
_diffrn_reflns_theta_min         2.513
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68699
_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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       prism
_exptl_crystal_F_000             4464
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.40(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     716
_refine_ls_number_reflns         10998
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0759
_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^)+(0.0789P)^2^+19.3704P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.1910
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                10599
_reflns_number_total             10998
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            aw5097sup1.cif
_cod_data_source_block           dadsa_hmbc_2
_cod_depositor_comments
'Adding full bibliography for 2312709--2312717.cif.'
_cod_original_cell_volume        10320.10(13)
_cod_database_code               2312717
_cod_database_fobs_code          2312717
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C39 H36 N2 O9'
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.889
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.60(16)
 0.40(16)
2. 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
3. Uiso/Uaniso restraints and constraints
Uanis(O15) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(O7) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(O13A)=Sof(H13c)=Sof(H13d)=1-FVAR(1)
 Sof(O13)=Sof(H13a)=Sof(H13b)=FVAR(1)
 Fixed X: O13A(0.68897)
 Fixed Y: O13A(0.08702)
 Fixed Z: O13A(0.74729)
5.a Free rotating group:
 O17(H17a,H17b), O13(H13a,H13b), O13A(H13c,H13d)
5.b Rotating group:
 O18(H18a,H18b), O16(H16a,H16b), O14(H14a,H14b)
5.c Secondary CH2 refined with riding coordinates:
 O15(H15a,H15b)
5.d Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C36(H36), C43(H43), C46(H46), C16(H16), C42(H42), C26(H26),
 C52(H52), C4(H4a), C3(H3a), C15(H15), C33(H33), C53(H53), C45(H45), C24(H24),
 C34(H34), C55(H55), C56(H56), C23(H23)
5.e Idealised Me refined as rotating group:
 C57(H57a,H57b,H57c), C47(H47a,H47b,H47c), C48(H48a,H48b,H48c), C49(H49a,H49b,
 H49c), C58(H58a,H58b,H58c), C59(H59a,H59b,H59c)
5.f Idealised tetrahedral OH refined as rotating group:
 O12(H12), O4(H4), O3(H3), O8(H8)
;
_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 1.632
_oxdiff_exptl_absorpt_empirical_full_min 0.615