#------------------------------------------------------------------------------
#$Date: 2024-12-07 19:04:45 +0200 (Sat, 07 Dec 2024) $
#$Revision: 296757 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/27/2312710.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2312710
loop_
_publ_author_name
'Kanthapazham, Rajakumar'
'Osipov, Artyom A.'
'Zherebtsov, Dmitry A.'
'Efremov, Andrey N.'
'Nayfert, Sergey A.'
'Adonin, Sergey A.'
'Spiridonova, Dar'ya V.'
'Atapin, Sergey V.'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    105.00 153.00   0.50    1.20    --  113.25  15.00 -30.00   96
  2  ω    102.00 165.00   0.50    1.20    --  113.25  61.00  60.00  126
  3  ω     34.00 121.00   0.50    0.30    --   47.38  15.00 -30.00  174
  4  ω    -64.00 -38.00   0.50    1.20    -- -106.00 125.00 -30.00   52
  5  ω   -107.00 -69.00   0.50    1.20    -- -106.00 125.00 -30.00   76
  6  ω   -112.00 -56.00   0.50    1.20    -- -106.00 125.00  60.00  112
  7  ω    -70.00 -34.00   0.50    1.20    -- -106.00  61.00  90.00   72
  8  ω    -60.00 -33.00   0.50    1.20    -- -106.00  61.00 150.00   54
  9  ω    -71.00 -39.00   0.50    1.20    -- -106.00  61.00 -30.00   64
 10  ω    -69.00 -34.00   0.50    1.20    -- -106.00  61.00  60.00   70
 11  ω    -64.00 -38.00   0.50    1.20    -- -106.00  61.00 -60.00   52
 12  ω    -15.00  11.00   0.50    0.30    --  -47.38  15.00 -30.00   52
 13  ω    -60.00 -34.00   0.50    1.20    -- -106.00  61.00 -90.00   52
 14  ω    -71.00 -45.00   0.50    1.20    -- -106.00  61.00-120.00   52
 15  ω    -71.00 -33.00   0.50    1.20    -- -106.00  61.00-180.00   76
 16  ω   -174.00-136.00   0.50    1.20    -- -106.00 -15.00-120.00   76
 17  ω   -121.00 -92.00   0.50    1.20    -- -106.00 -15.00-120.00   58
 18  ω   -159.00 -92.00   0.50    1.20    -- -106.00 -15.00 159.00  134
 19  ω   -107.00 -42.00   0.50    0.30    --  -47.38 -15.00 159.00  130
 20  ω    -21.00   9.00   0.50    0.30    --   47.38 -15.00 159.00   60
 21  ω      0.00  42.00   0.50    0.30    --   47.38 -37.00   0.00   84
 22  ω     44.00  69.00   0.50    1.20    --  113.25 -61.00-150.00   50
 23  ω     43.00  68.00   0.50    1.20    --  113.25 -61.00  30.00   50
 24  ω     42.00  88.00   0.50    1.20    --  113.25 -77.00  90.00   92
 25  ω     78.00 104.00   0.50    1.20    --  113.25 -94.00  30.00   52
 26  ω     78.00 103.00   0.50    1.20    --  113.25 -94.00   0.00   50
 27  ω     43.00 110.00   0.50    1.20    --  113.25-125.00  30.00  134
 28  ω     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       'ω 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/[σ²(Fo²)+(0.0571P)²+6.9331P] where P=(Fo²+2Fc²)/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 > 2σ(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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.31876(2) -0.01283(3) 0.30746(2) 0.02406(14) Uani 1 1 d . . . . .
N1 N 0.33888(16) 0.5098(4) 0.5145(3) 0.0235(7) Uani 1 1 d . . . . .
C1 C 0.38922(17) 0.5115(4) 0.4444(4) 0.0220(8) Uani 1 1 d . . . . .
C5 C 0.44599(15) 0.3737(5) 0.3076(4) 0.0270(8) Uani 1 1 d . . . . .
H5 H 0.454817 0.278702 0.265914 0.032 Uiso 1 1 calc R U . . .
C8 C 0.29044(19) 0.4900(5) 0.4271(4) 0.0293(10) Uani 1 1 d . . . . .
H8A H 0.289870 0.577321 0.368131 0.044 Uiso 1 1 calc R U . . .
H8B H 0.256933 0.492085 0.471977 0.044 Uiso 1 1 calc R U . . .
H8C H 0.293199 0.387931 0.384663 0.044 Uiso 1 1 calc R U . . .
C6 C 0.40229(15) 0.3742(5) 0.3819(4) 0.0265(8) Uani 1 1 d . . . . .
H6 H 0.381137 0.280455 0.390315 0.032 Uiso 1 1 calc R U . . .
C4 C 0.47754(17) 0.5106(4) 0.2925(4) 0.0229(9) Uani 1 1 d . . . . .
C2 C 0.42100(16) 0.6480(5) 0.4350(4) 0.0277(8) Uani 1 1 d . . . . .
H2 H 0.412877 0.741213 0.479674 0.033 Uiso 1 1 calc R U . . .
C9 C 0.33028(16) 0.6621(5) 0.5831(4) 0.0284(8) Uani 1 1 d . . . . .
H9A H 0.361299 0.680552 0.639540 0.043 Uiso 1 1 calc R U . . .
H9B H 0.297001 0.653617 0.628388 0.043 Uiso 1 1 calc R U . . .
H9C H 0.326930 0.751284 0.526030 0.043 Uiso 1 1 calc R U . . .
C3 C 0.46465(16) 0.6459(5) 0.3597(4) 0.0288(8) Uani 1 1 d . . . . .
H3 H 0.486399 0.738889 0.353395 0.035 Uiso 1 1 calc R U . . .
C7 C 0.33963(17) 0.3739(5) 0.6037(4) 0.0312(9) Uani 1 1 d . . . . .
H7A H 0.342179 0.272588 0.560181 0.047 Uiso 1 1 calc R U . . .
H7B H 0.306167 0.375566 0.648782 0.047 Uiso 1 1 calc R U . . .
H7C H 0.371027 0.385272 0.660258 0.047 Uiso 1 1 calc R U . . .
O1 O 0.4514(4) 0.0009(7) 0.1783(11) 0.078(2) Uani 0.667(10) 1 d G U P A -2
H1A H 0.461508 0.012862 0.104349 0.117 Uiso 0.667(10) 1 d G U P A -2
H1B H 0.481317 0.008609 0.222390 0.117 Uiso 0.667(10) 1 d G U P A -2
O1A O 0.4053(8) -0.0170(16) 0.0695(19) 0.078(2) Uani 0.333(10) 1 d G U P A -1
H1AA H 0.426859 -0.097779 0.060115 0.117 Uiso 0.333(10) 1 d G U P A -1
H1AB H 0.401684 -0.010683 0.147244 0.117 Uiso 0.333(10) 1 d G U P A -1
O2 O 0.5237(8) 0.0330(14) 0.0626(19) 0.128(6) Uani 0.5 1 d G U P B -1
H2A H 0.554359 -0.003080 0.092957 0.192 Uiso 0.5 1 d G U P B -1
H2B H 0.506107 -0.051833 0.038059 0.192 Uiso 0.5 1 d G U P B -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 108.7(3) . . ?
C1 N1 C9 113.0(3) . . ?
C1 N1 C7 111.1(3) . . ?
C9 N1 C8 106.9(3) . . ?
C9 N1 C7 108.1(3) . . ?
C7 N1 C8 108.9(3) . . ?
C6 C1 N1 117.8(3) . . ?
C6 C1 C2 120.2(4) . . ?
C2 C1 N1 122.0(3) . . ?
C6 C5 H5 119.4 . . ?
C6 C5 C4 121.2(4) . . ?
C4 C5 H5 119.4 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 H6 120.0 . . ?
C5 C4 C4 120.6(3) . 2_655 ?
C3 C4 C5 117.6(4) . . ?
C3 C4 C4 121.9(3) . 2_655 ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 H2 120.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C3 H3 119.1 . . ?
C2 C3 C4 121.8(4) . . ?
C2 C3 H3 119.1 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H1A O1 H1B 104.6 . . ?
H1AA O1A H1AB 104.5 . . ?
H2A O2 H2B 104.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.488(5) . ?
N1 C8 1.515(6) . ?
N1 C9 1.504(5) . ?
N1 C7 1.507(5) . ?
C1 C6 1.387(5) . ?
C1 C2 1.393(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(5) . ?
C5 C4 1.400(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C6 H6 0.9500 . ?
C4 C4 1.480(8) 2_655 ?
C4 C3 1.400(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C3 H3 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O1 H1A 0.8698 . ?
O1 H1B 0.8697 . ?
O1A H1AA 0.8701 . ?
O1A H1AB 0.8697 . ?
O2 H2A 0.8698 . ?
O2 H2B 0.8700 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C6 C5 174.7(4) . . . . ?
N1 C1 C2 C3 -174.3(4) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C5 C4 C3 C2 -2.5(6) . . . . ?
C8 N1 C1 C6 -64.2(4) . . . . ?
C8 N1 C1 C2 112.2(4) . . . . ?
C6 C1 C2 C3 2.0(6) . . . . ?
C6 C5 C4 C4 -176.7(4) . . . 2_655 ?
C6 C5 C4 C3 2.7(6) . . . . ?
C4 C5 C6 C1 -0.7(6) . . . . ?
C4 C4 C3 C2 177.0(5) 2_655 . . . ?
C2 C1 C6 C5 -1.8(6) . . . . ?
C9 N1 C1 C6 177.3(4) . . . . ?
C9 N1 C1 C2 -6.3(5) . . . . ?
C7 N1 C1 C6 55.7(5) . . . . ?
C7 N1 C1 C2 -128.0(4) . . . . ?
