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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/00/4500031.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4500031
loop_
_publ_author_name
'Gagnon, Eric'
'Maris, Thierry'
'Arseneault, Pierre-Marc'
'Maly, Kenneth E.'
'Wuest,James D'
_publ_section_title
;
 Structural Features in Crystals of Derivatives of Benzene with Multiple
 Contiguous Phenyl Substituents
;
_journal_name_full               'Cryst. Growth & Design'
_journal_page_first              648
_journal_page_last               657
_journal_paper_doi               10.1021/cg9010746
_journal_volume                  10
_journal_year                    2010
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C32 H26'
_chemical_formula_sum            'C32 H26'
_chemical_formula_weight         410.53
_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
_cell_angle_beta                 95.395(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1336(2)
_cell_length_b                   8.8786(1)
_cell_length_c                   11.5617(2)
_cell_measurement_reflns_used    14299
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.83
_cell_measurement_theta_min      6.39
_cell_volume                     1137.82(3)
_computing_cell_refinement       'APEX II (Bruker, 2006)'
_computing_data_collection       'APEX II (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.2
_diffrn_measured_fraction_theta_full 0.872
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18301
_diffrn_reflns_theta_full        67.99
_diffrn_reflns_theta_max         67.99
_diffrn_reflns_theta_min         6.39
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_T_max  0.9032
_exptl_absorpt_correction_T_min  0.7527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0539P)²+0.2990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                1780
_reflns_number_total             1810
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            deposit.cif
_cod_data_source_block           DMTPB
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4500031
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.06834(11) 0.88442(12) 0.45662(8) 0.0213(3) Uani 1 1 d .
C10 C 0.14273(11) 0.76051(12) 0.41127(9) 0.0223(3) Uani 1 1 d .
C11 C 0.24849(12) 0.71141(12) 0.47270(10) 0.0260(3) Uani 1 1 d .
H11 H 0.2749 0.7568 0.5450 0.031 Uiso 1 1 calc R
C12 C 0.31615(12) 0.59633(13) 0.42940(10) 0.0282(3) Uani 1 1 d .
H12 H 0.3884 0.5638 0.4723 0.034 Uiso 1 1 calc R
C13 C 0.27875(12) 0.52872(12) 0.32392(10) 0.0281(3) Uani 1 1 d .
H13 H 0.3252 0.4504 0.2943 0.034 Uiso 1 1 calc R
C14 C 0.17308(12) 0.57658(13) 0.26234(9) 0.0285(3) Uani 1 1 d .
H14 H 0.1466 0.5307 0.1902 0.034 Uiso 1 1 calc R
C15 C 0.10567(12) 0.69140(12) 0.30576(9) 0.0261(3) Uani 1 1 d .
H15 H 0.0332 0.7234 0.2629 0.031 Uiso 1 1 calc R
C2 C 0.10776(11) 1.03465(12) 0.45174(8) 0.0214(3) Uani 1 1 d .
C20 C 0.22416(11) 1.07080(12) 0.40379(9) 0.0234(3) Uani 1 1 d .
C21 C 0.32205(12) 1.12201(13) 0.47742(10) 0.0292(3) Uani 1 1 d .
H21 H 0.3139 1.1335 0.5580 0.035 Uiso 1 1 calc R
C22 C 0.43060(13) 1.15622(14) 0.43507(12) 0.0369(4) Uani 1 1 d .
H22 H 0.4966 1.1899 0.4867 0.044 Uiso 1 1 calc R
C23 C 0.44378(14) 1.14168(15) 0.31774(13) 0.0396(4) Uani 1 1 d .
H23 H 0.5182 1.1668 0.2885 0.047 Uiso 1 1 calc R
C24 C 0.34774(14) 1.09028(14) 0.24325(12) 0.0384(4) Uani 1 1 d .
H24 H 0.3563 1.0798 0.1627 0.046 Uiso 1 1 calc R
C25 C 0.23916(13) 1.05408(13) 0.28604(10) 0.0302(3) Uani 1 1 d .
H25 H 0.1742 1.0174 0.2345 0.036 Uiso 1 1 calc R
C3 C 0.03833(11) 1.15099(12) 0.49437(9) 0.0217(3) Uani 1 1 d .
C30 C 0.07496(12) 1.31353(12) 0.48228(10) 0.0272(3) Uani 1 1 d .
H30A H 0.0028 1.3754 0.4639 0.041 Uiso 1 1 calc R
H30B H 0.1281 1.3225 0.4197 0.041 Uiso 1 1 calc R
H30C H 0.1177 1.3481 0.5554 0.041 Uiso 1 1 calc R
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'
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_publ_flag
C3 C1 C2 120.61(10) 3_576 y
C3 C1 C10 119.61(10) 3_576 y
C2 C1 C10 119.76(11) . y
C11 C10 C15 118.51(11) . y
C11 C10 C1 121.41(10) . y
C15 C10 C1 120.07(10) . y
C10 C11 C12 120.61(10) . y
C10 C11 H11 119.7 . y
C12 C11 H11 119.7 . y
C13 C12 C11 120.43(11) . y
C13 C12 H12 119.8 . y
C11 C12 H12 119.8 . y
C14 C13 C12 119.33(11) . y
C14 C13 H13 120.3 . y
C12 C13 H13 120.3 . y
C13 C14 C15 120.14(10) . y
C13 C14 H14 119.9 . y
C15 C14 H14 119.9 . y
C14 C15 C10 120.98(11) . y
C14 C15 H15 119.5 . y
C10 C15 H15 119.5 . y
C3 C2 C1 119.89(11) . y
C3 C2 C20 119.83(10) . y
C1 C2 C20 120.27(10) . y
C21 C20 C25 118.17(12) . y
C21 C20 C2 119.98(10) . y
C25 C20 C2 121.85(11) . y
C22 C21 C20 121.03(11) . y
C22 C21 H21 119.5 . y
C20 C21 H21 119.5 . y
C21 C22 C23 120.29(13) . y
C21 C22 H22 119.9 . y
C23 C22 H22 119.9 . y
C22 C23 C24 119.54(13) . y
C22 C23 H23 120.2 . y
C24 C23 H23 120.2 . y
C23 C24 C25 120.16(12) . y
C23 C24 H24 119.9 . y
C25 C24 H24 119.9 . y
C24 C25 C20 120.79(12) . y
C24 C25 H25 119.6 . y
C20 C25 H25 119.6 . y
C1 C3 C2 119.49(10) 3_576 y
C1 C3 C30 119.95(10) 3_576 y
C2 C3 C30 120.49(11) . y
C3 C30 H30A 109.5 . y
C3 C30 H30B 109.5 . y
H30A C30 H30B 109.5 . y
C3 C30 H30C 109.5 . y
H30A C30 H30C 109.5 . y
H30B C30 H30C 109.5 . y
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
C1 C3 1.3989(17) 3_576 y
C1 C2 1.4069(15) . y
C1 C10 1.5010(15) . y
C10 C11 1.3870(17) . y
C10 C15 1.3929(16) . y
C11 C12 1.3903(17) . y
C11 H11 0.9500 . y
C12 C13 1.3876(17) . y
C12 H12 0.9500 . y
C13 C14 1.3834(18) . y
C13 H13 0.9500 . y
C14 C15 1.3876(17) . y
C14 H14 0.9500 . y
C15 H15 0.9500 . y
C2 C3 1.4068(16) . y
C2 C20 1.4917(17) . y
C20 C21 1.3946(18) . y
C20 C25 1.3951(16) . y
C21 C22 1.380(2) . y
C21 H21 0.9500 . y
C22 C23 1.384(2) . y
C22 H22 0.9500 . y
C23 C24 1.386(2) . y
C23 H23 0.9500 . y
C24 C25 1.386(2) . y
C24 H24 0.9500 . y
C25 H25 0.9500 . y
C3 C1 1.3989(17) 3_576 y
C3 C30 1.5097(15) . y
C30 H30A 0.9800 . y
C30 H30B 0.9800 . y
C30 H30C 0.9800 . y
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_4
_geom_torsion_publ_flag
C3 C1 C10 C11 -103.77(13) 3_576 . y
C2 C1 C10 C11 74.89(14) . . y
C3 C1 C10 C15 75.78(13) 3_576 . y
C2 C1 C10 C15 -105.56(13) . . y
C15 C10 C11 C12 0.35(17) . . y
C1 C10 C11 C12 179.91(10) . . y
C10 C11 C12 C13 -0.04(18) . . y
C11 C12 C13 C14 -0.24(17) . . y
C12 C13 C14 C15 0.21(17) . . y
C13 C14 C15 C10 0.11(18) . . y
C11 C10 C15 C14 -0.38(17) . . y
C1 C10 C15 C14 -179.95(10) . . y
C3 C1 C2 C3 -1.24(16) 3_576 . y
C10 C1 C2 C3 -179.89(9) . . y
C3 C1 C2 C20 177.48(9) 3_576 . y
C10 C1 C2 C20 -1.17(15) . . y
C3 C2 C20 C21 68.26(14) . . y
C1 C2 C20 C21 -110.46(12) . . y
C3 C2 C20 C25 -112.14(12) . . y
C1 C2 C20 C25 69.14(14) . . y
C25 C20 C21 C22 0.42(17) . . y
C2 C20 C21 C22 -179.97(11) . . y
C20 C21 C22 C23 0.70(19) . . y
C21 C22 C23 C24 -1.0(2) . . y
C22 C23 C24 C25 0.2(2) . . y
C23 C24 C25 C20 0.97(19) . . y
C21 C20 C25 C24 -1.25(17) . . y
C2 C20 C25 C24 179.15(11) . . y
C1 C2 C3 C1 1.23(16) . 3_576 y
C20 C2 C3 C1 -177.50(9) . 3_576 y
C1 C2 C3 C30 -175.79(10) . . y
C20 C2 C3 C30 5.48(15) . . y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 5082699
