#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226652.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_2226652
loop_
_publ_author_name
'Lei, Ke-Wei'
'Xia, Dong-Guo'
'Li, Jie'
_publ_section_title
;
 1,3-Bis(3,5-dimethylphenyl)-5-methylbenzene
;
_journal_coeditor_code           RZ2458
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1840
_journal_paper_doi               10.1107/S1600536810024013
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C23 H24'
_chemical_formula_moiety         'C23 H24'
_chemical_formula_sum            'C23 H24'
_chemical_formula_weight         300.42
_chemical_name_systematic
;
1,3-Bis(3,5-dimethylphenyl)-5-methylbenzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.839(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.955(2)
_cell_length_b                   7.6081(12)
_cell_length_c                   16.207(2)
_cell_measurement_reflns_used    4929
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.60
_cell_volume                     1765.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12155
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0676P)²+0.6595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                2485
_reflns_number_total             3087
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz2458.cif
_cod_data_source_block           I
_cod_original_cell_volume        1765.0(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226652
_cod_database_fobs_code          2226652
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.28892(13) 0.9286(3) -0.18056(11) 0.0430(5) Uani d . 1 . .
H H1A 0.3479 0.9757 -0.1822 0.064 Uiso calc R 1 . .
H H1B 0.2406 1.0136 -0.2032 0.064 Uiso calc R 1 . .
H H1C 0.2756 0.8235 -0.2147 0.064 Uiso calc R 1 . .
C C2 0.29293(12) 0.8859(2) -0.08860(10) 0.0323(4) Uani d . 1 . .
C C3 0.21125(11) 0.8739(2) -0.06402(10) 0.0317(4) Uani d . 1 . .
H H3A 0.1544 0.9012 -0.1039 0.038 Uiso calc R 1 . .
C C4 0.21242(11) 0.8221(2) 0.01890(10) 0.0293(4) Uani d . 1 . .
C C5 0.29861(11) 0.7810(2) 0.07781(10) 0.0289(4) Uani d . 1 . .
H H5A 0.3004 0.7432 0.1328 0.035 Uiso calc R 1 . .
C C6 0.38219(11) 0.7953(2) 0.05594(10) 0.0292(4) Uani d . 1 . .
C C7 0.37750(11) 0.8499(2) -0.02774(10) 0.0325(4) Uani d . 1 . .
H H7A 0.4326 0.8623 -0.0429 0.039 Uiso calc R 1 . .
C C8 0.12366(11) 0.8067(2) 0.04287(10) 0.0290(4) Uani d . 1 . .
C C9 0.04176(11) 0.7501(2) -0.01771(10) 0.0332(4) Uani d . 1 . .
H H9A 0.0432 0.7229 -0.0733 0.040 Uiso calc R 1 . .
C C10 -0.04181(11) 0.7333(2) 0.00311(11) 0.0357(4) Uani d . 1 . .
C C11 -0.04208(11) 0.7735(2) 0.08674(11) 0.0357(4) Uani d . 1 . .
H H11A -0.0972 0.7609 0.1017 0.043 Uiso calc R 1 . .
C C12 0.03733(11) 0.8317(2) 0.14839(11) 0.0329(4) Uani d . 1 . .
C C13 0.12016(11) 0.8473(2) 0.12570(10) 0.0300(4) Uani d . 1 . .
H H13A 0.1740 0.8856 0.1667 0.036 Uiso calc R 1 . .
C C14 -0.12950(12) 0.6743(3) -0.06379(13) 0.0489(5) Uani d . 1 . .
H H14A -0.1131 0.6047 -0.1066 0.073 Uiso calc R 1 . .
H H14B -0.1645 0.7753 -0.0906 0.073 Uiso calc R 1 . .
H H14C -0.1668 0.6052 -0.0367 0.073 Uiso calc R 1 . .
C C15 0.03426(13) 0.8813(3) 0.23773(12) 0.0474(5) Uani d . 1 . .
H H15A 0.0840 0.8231 0.2798 0.071 Uiso calc R 1 . .
H H15B -0.0246 0.8462 0.2451 0.071 Uiso calc R 1 . .
H H15C 0.0414 1.0063 0.2451 0.071 Uiso calc R 1 . .
C C16 0.47339(11) 0.7497(2) 0.11903(10) 0.0286(4) Uani d . 1 . .
C C17 0.48839(11) 0.7751(2) 0.20766(10) 0.0294(4) Uani d . 1 . .
H H17A 0.4406 0.8217 0.2270 0.035 Uiso calc R 1 . .
C C18 0.57282(11) 0.7322(2) 0.26727(10) 0.0302(4) Uani d . 1 . .
C C19 0.64405(11) 0.6637(2) 0.23696(11) 0.0321(4) Uani d . 1 . .
H H19A 0.7006 0.6331 0.2763 0.039 Uiso calc R 1 . .
C C20 0.63239(11) 0.6404(2) 0.14940(11) 0.0318(4) Uani d . 1 . .
C C21 0.54670(11) 0.6821(2) 0.09147(10) 0.0310(4) Uani d . 1 . .
H H21A 0.5379 0.6646 0.0329 0.037 Uiso calc R 1 . .
C C22 0.58804(12) 0.7640(3) 0.36219(11) 0.0404(4) Uani d . 1 . .
H H22A 0.5334 0.8179 0.3708 0.061 Uiso calc R 1 . .
H H22B 0.6408 0.8403 0.3837 0.061 Uiso calc R 1 . .
H H22C 0.5996 0.6541 0.3925 0.061 Uiso calc R 1 . .
C C23 0.71275(12) 0.5809(3) 0.11702(12) 0.0437(5) Uani d . 1 . .
H H23A 0.7562 0.5144 0.1612 0.066 Uiso calc R 1 . .
H H23B 0.7437 0.6818 0.1026 0.066 Uiso calc R 1 . .
H H23C 0.6893 0.5088 0.0668 0.066 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C7 C2 C3 . . 118.56(14) ?
C7 C2 C1 . . 120.78(15) ?
C3 C2 C1 . . 120.60(15) ?
C2 C3 C4 . . 121.76(15) ?
C2 C3 H3A . . 119.1 ?
C4 C3 H3A . . 119.1 ?
C3 C4 C5 . . 118.18(14) ?
C3 C4 C8 . . 120.59(14) ?
C5 C4 C8 . . 121.21(14) ?
C6 C5 C4 . . 121.59(14) ?
C6 C5 H5A . . 119.2 ?
C4 C5 H5A . . 119.2 ?
C5 C6 C7 . . 118.08(14) ?
C5 C6 C16 . . 121.04(14) ?
C7 C6 C16 . . 120.86(14) ?
C2 C7 C6 . . 121.78(14) ?
C2 C7 H7A . . 119.1 ?
C6 C7 H7A . . 119.1 ?
C13 C8 C9 . . 118.38(14) ?
C13 C8 C4 . . 121.21(14) ?
C9 C8 C4 . . 120.41(14) ?
C10 C9 C8 . . 121.59(15) ?
C10 C9 H9A . . 119.2 ?
C8 C9 H9A . . 119.2 ?
C11 C10 C9 . . 118.20(15) ?
C11 C10 C14 . . 121.26(16) ?
C9 C10 C14 . . 120.54(16) ?
C12 C11 C10 . . 121.97(15) ?
C12 C11 H11A . . 119.0 ?
C10 C11 H11A . . 119.0 ?
C11 C12 C13 . . 118.58(15) ?
C11 C12 C15 . . 120.93(15) ?
C13 C12 C15 . . 120.48(15) ?
C8 C13 C12 . . 121.27(15) ?
C8 C13 H13A . . 119.4 ?
C12 C13 H13A . . 119.4 ?
C10 C14 H14A . . 109.5 ?
C10 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C10 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C12 C15 H15A . . 109.5 ?
C12 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C12 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C21 C16 C17 . . 118.10(14) ?
C21 C16 C6 . . 120.92(14) ?
C17 C16 C6 . . 120.97(14) ?
C18 C17 C16 . . 121.62(14) ?
C18 C17 H17A . . 119.2 ?
C16 C17 H17A . . 119.2 ?
C17 C18 C19 . . 118.39(15) ?
C17 C18 C22 . . 120.69(14) ?
C19 C18 C22 . . 120.90(15) ?
C20 C19 C18 . . 121.59(15) ?
C20 C19 H19A . . 119.2 ?
C18 C19 H19A . . 119.2 ?
C21 C20 C19 . . 118.64(14) ?
C21 C20 C23 . . 120.27(15) ?
C19 C20 C23 . . 121.00(15) ?
C20 C21 C16 . . 121.63(15) ?
C20 C21 H21A . . 119.2 ?
C16 C21 H21A . . 119.2 ?
C18 C22 H22A . . 109.5 ?
C18 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C18 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C20 C23 H23A . . 109.5 ?
C20 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C20 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.509(2) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C7 . 1.387(2) ?
C2 C3 . 1.393(2) ?
C3 C4 . 1.396(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.399(2) ?
C4 C8 . 1.492(2) ?
C5 C6 . 1.399(2) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.401(2) ?
C6 C16 . 1.489(2) ?
C7 H7A . 0.9300 ?
C8 C13 . 1.393(2) ?
C8 C9 . 1.398(2) ?
C9 C10 . 1.392(2) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.391(2) ?
C10 C14 . 1.508(2) ?
C11 C12 . 1.385(2) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.396(2) ?
C12 C15 . 1.510(2) ?
C13 H13A . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 C21 . 1.397(2) ?
C16 C17 . 1.401(2) ?
C17 C18 . 1.388(2) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.397(2) ?
C18 C22 . 1.508(2) ?
C19 C20 . 1.390(2) ?
C19 H19A . 0.9300 ?
C20 C21 . 1.388(2) ?
C20 C23 . 1.513(2) ?
C21 H21A . 0.9300 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C23 H23A . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C2 C3 C4 . . . . -1.9(2) ?
C1 C2 C3 C4 . . . . 175.21(15) ?
C2 C3 C4 C5 . . . . -0.3(2) ?
C2 C3 C4 C8 . . . . -178.69(15) ?
C3 C4 C5 C6 . . . . 1.7(2) ?
C8 C4 C5 C6 . . . . -179.86(14) ?
C4 C5 C6 C7 . . . . -1.0(2) ?
C4 C5 C6 C16 . . . . -179.49(14) ?
C3 C2 C7 C6 . . . . 2.6(2) ?
C1 C2 C7 C6 . . . . -174.43(15) ?
C5 C6 C7 C2 . . . . -1.3(2) ?
C16 C6 C7 C2 . . . . 177.26(15) ?
C3 C4 C8 C13 . . . . -145.64(16) ?
C5 C4 C8 C13 . . . . 36.0(2) ?
C3 C4 C8 C9 . . . . 34.7(2) ?
C5 C4 C8 C9 . . . . -143.73(16) ?
C13 C8 C9 C10 . . . . -0.2(2) ?
C4 C8 C9 C10 . . . . 179.53(15) ?
C8 C9 C10 C11 . . . . -0.5(2) ?
C8 C9 C10 C14 . . . . 179.17(16) ?
C9 C10 C11 C12 . . . . 1.1(2) ?
C14 C10 C11 C12 . . . . -178.51(16) ?
C10 C11 C12 C13 . . . . -1.1(2) ?
C10 C11 C12 C15 . . . . 177.55(17) ?
C9 C8 C13 C12 . . . . 0.2(2) ?
C4 C8 C13 C12 . . . . -179.50(15) ?
C11 C12 C13 C8 . . . . 0.4(2) ?
C15 C12 C13 C8 . . . . -178.23(16) ?
C5 C6 C16 C21 . . . . 148.88(16) ?
C7 C6 C16 C21 . . . . -29.6(2) ?
C5 C6 C16 C17 . . . . -31.8(2) ?
C7 C6 C16 C17 . . . . 149.78(15) ?
C21 C16 C17 C18 . . . . -1.0(2) ?
C6 C16 C17 C18 . . . . 179.61(14) ?
C16 C17 C18 C19 . . . . 0.6(2) ?
C16 C17 C18 C22 . . . . 178.76(15) ?
C17 C18 C19 C20 . . . . 0.8(2) ?
C22 C18 C19 C20 . . . . -177.33(15) ?
C18 C19 C20 C21 . . . . -1.8(2) ?
C18 C19 C20 C23 . . . . 174.69(16) ?
C19 C20 C21 C16 . . . . 1.3(2) ?
C23 C20 C21 C16 . . . . -175.17(16) ?
C17 C16 C21 C20 . . . . 0.0(2) ?
C6 C16 C21 C20 . . . . 179.43(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745382
2 PubChem 91433649
