#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/47/2214763.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_2214763
loop_
_publ_author_name
'Suzuki, Noriyuki'
'Hashizume, Daisuke'
'Chihara, Teiji'
_publ_section_title
;
 1,1,6,6-Tetrakis(4-ethylphenyl)-1,2,3,4,5-hexapentaene
;
_journal_coeditor_code           IS2187
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3436
_journal_page_last               o3436
_journal_paper_doi               10.1107/S1600536807032576
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C38 H36'
_chemical_formula_moiety         'C38 H36'
_chemical_formula_sum            'C38 H36'
_chemical_formula_weight         492.67
_chemical_name_systematic
;
1,1,6,6-Tetrakis(4-ethylphenyl)-1,2,3,4,5-hexapentaene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                93.849(7)
_cell_angle_beta                 96.353(6)
_cell_angle_gamma                105.908(8)
_cell_formula_units_Z            1
_cell_length_a                   6.233(3)
_cell_length_b                   7.819(3)
_cell_length_c                   15.060(6)
_cell_measurement_reflns_used    1421
_cell_measurement_temperature    90
_cell_measurement_theta_max      31.7604
_cell_measurement_theta_min      2.7227
_cell_volume                     697.9(5)
_computing_cell_refinement       'CrystalClear SM'
_computing_data_collection       'CrystalClear SM (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear SM'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10184
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.37
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0578
_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)+(0.0818P)²+0.1721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1659
_reflns_number_gt                2271
_reflns_number_total             3169
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2187.cif
_cod_data_source_block           I
_cod_original_cell_volume        697.8(5)
_cod_database_code               2214763
_cod_database_fobs_code          2214763
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.2372(3) 0.5597(2) 0.31075(10) 0.0184(3) Uani d . 1
C C2 0.3440(3) 0.5306(2) 0.38872(11) 0.0213(4) Uani d . 1
C C3 0.4442(3) 0.5093(2) 0.46204(10) 0.0219(4) Uani d . 1
C C4 0.2487(3) 0.4593(2) 0.22565(10) 0.0188(3) Uani d . 1
C C5 0.0806(3) 0.4334(2) 0.15174(11) 0.0210(4) Uani d . 1
H H5 -0.0388 0.4863 0.1552 0.025 Uiso calc R 1
C C6 0.0876(3) 0.3317(2) 0.07406(11) 0.0224(4) Uani d . 1
H H7 -0.0276 0.3162 0.0248 0.027 Uiso calc R 1
C C7 0.2590(3) 0.2514(2) 0.06604(11) 0.0203(4) Uani d . 1
C C8 0.4270(3) 0.2776(2) 0.13952(11) 0.0219(4) Uani d . 1
H H8 0.5456 0.2238 0.1358 0.026 Uiso calc R 1
C C9 0.4237(3) 0.3804(2) 0.21753(11) 0.0214(4) Uani d . 1
H H9 0.5411 0.3979 0.2661 0.026 Uiso calc R 1
C C10 0.2656(3) 0.1413(2) -0.01962(11) 0.0246(4) Uani d . 1
H H10A 0.1135 0.1035 -0.0547 0.030 Uiso calc R 1
H H10B 0.3064 0.0322 -0.0041 0.030 Uiso calc R 1
C C11 0.4330(3) 0.2429(3) -0.07754(12) 0.0311(4) Uani d . 1
H H11A 0.4329 0.1650 -0.1313 0.047 Uiso calc R 1
H H11B 0.5840 0.2806 -0.0432 0.047 Uiso calc R 1
H H11C 0.3897 0.3483 -0.0953 0.047 Uiso calc R 1
C C12 0.1089(3) 0.6941(2) 0.31389(10) 0.0193(4) Uani d . 1
C C13 -0.0162(3) 0.7073(2) 0.38373(11) 0.0229(4) Uani d . 1
H H13 -0.0273 0.6242 0.4274 0.027 Uiso calc R 1
C C14 -0.1250(3) 0.8395(2) 0.39083(12) 0.0251(4) Uani d . 1
H H14 -0.2101 0.8450 0.4390 0.030 Uiso calc R 1
C C15 -0.1108(3) 0.9648(2) 0.32793(11) 0.0233(4) Uani d . 1
C C16 0.0145(3) 0.9506(2) 0.25801(11) 0.0230(4) Uani d . 1
H H16 0.0269 1.0345 0.2147 0.028 Uiso calc R 1
C C17 0.1212(3) 0.8180(2) 0.25001(11) 0.0215(4) Uani d . 1
H H17 0.2033 0.8107 0.2010 0.026 Uiso calc R 1
C C18 -0.2284(4) 1.1101(3) 0.33273(14) 0.0367(5) Uani d . 1
H H18A -0.1119 1.2269 0.3447 0.044 Uiso calc R 1
H H18B -0.3142 1.1076 0.2730 0.044 Uiso calc R 1
C C19 -0.3871(3) 1.0999(3) 0.40214(13) 0.0320(4) Uani d . 1
H H19A -0.4614 1.1949 0.3965 0.048 Uiso calc R 1
H H19B -0.3022 1.1150 0.4623 0.048 Uiso calc R 1
H H19C -0.5009 0.9833 0.3927 0.048 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_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C4 . 120.27(14) no
C2 C1 C12 . 117.92(14) no
C4 C1 C12 . 121.81(13) no
C1 C2 C3 . 177.96(17) yes
C2 C3 C3 2_666 177.9(3) yes
C9 C4 C5 . 118.00(14) no
C9 C4 C1 . 120.79(13) no
C5 C4 C1 . 121.15(14) no
C6 C5 C4 . 120.54(15) no
C6 C5 H5 . 119.7 no
C4 C5 H5 . 119.7 no
C5 C6 C7 . 121.71(14) no
C5 C6 H7 . 119.1 no
C7 C6 H7 . 119.1 no
C6 C7 C8 . 117.80(14) no
C6 C7 C10 . 121.20(14) no
C8 C7 C10 . 121.00(15) no
C9 C8 C7 . 121.23(15) no
C9 C8 H8 . 119.4 no
C7 C8 H8 . 119.4 no
C8 C9 C4 . 120.71(14) no
C8 C9 H9 . 119.6 no
C4 C9 H9 . 119.6 no
C7 C10 C11 . 112.81(14) no
C7 C10 H10A . 109.0 no
C11 C10 H10A . 109.0 no
C7 C10 H10B . 109.0 no
C11 C10 H10B . 109.0 no
H10A C10 H10B . 107.8 no
C10 C11 H11A . 109.5 no
C10 C11 H11B . 109.5 no
H11A C11 H11B . 109.5 no
C10 C11 H11C . 109.5 no
H11A C11 H11C . 109.5 no
H11B C11 H11C . 109.5 no
C13 C12 C17 . 118.07(15) no
C13 C12 C1 . 120.59(14) no
C17 C12 C1 . 121.22(15) no
C14 C13 C12 . 121.30(15) no
C14 C13 H13 . 119.3 no
C12 C13 H13 . 119.3 no
C13 C14 C15 . 120.82(16) no
C13 C14 H14 . 119.6 no
C15 C14 H14 . 119.6 no
C16 C15 C14 . 117.61(15) no
C16 C15 C18 . 119.85(15) no
C14 C15 C18 . 122.53(16) no
C17 C16 C15 . 121.84(15) no
C17 C16 H16 . 119.1 no
C15 C16 H16 . 119.1 no
C16 C17 C12 . 120.34(15) no
C16 C17 H17 . 119.8 no
C12 C17 H17 . 119.8 no
C19 C18 C15 . 116.43(16) no
C19 C18 H18A . 108.2 no
C15 C18 H18A . 108.2 no
C19 C18 H18B . 108.2 no
C15 C18 H18B . 108.2 no
H18A C18 H18B . 107.3 no
C18 C19 H19A . 109.5 no
C18 C19 H19B . 109.5 no
H19A C19 H19B . 109.5 no
C18 C19 H19C . 109.5 no
H19A C19 H19C . 109.5 no
H19B C19 H19C . 109.5 no
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 . 1.349(2) yes
C1 C4 . 1.477(2) no
C1 C12 . 1.486(2) no
C2 C3 . 1.251(2) yes
C3 C3 2_666 1.310(3) yes
C4 C9 . 1.404(2) no
C4 C5 . 1.405(2) no
C5 C6 . 1.381(2) no
C5 H5 . 0.9500 no
C6 C7 . 1.392(2) no
C6 H7 . 0.9500 no
C7 C8 . 1.399(2) no
C7 C10 . 1.513(2) no
C8 C9 . 1.384(2) no
C8 H8 . 0.9500 no
C9 H9 . 0.9500 no
C10 C11 . 1.523(2) no
C10 H10A . 0.9900 no
C10 H10B . 0.9900 no
C11 H11A . 0.9800 no
C11 H11B . 0.9800 no
C11 H11C . 0.9800 no
C12 C13 . 1.391(2) no
C12 C17 . 1.404(2) no
C13 C14 . 1.387(2) no
C13 H13 . 0.9500 no
C14 C15 . 1.400(2) no
C14 H14 . 0.9500 no
C15 C16 . 1.395(2) no
C15 C18 . 1.513(2) no
C16 C17 . 1.382(2) no
C16 H16 . 0.9500 no
C17 H17 . 0.9500 no
C18 C19 . 1.508(3) no
C18 H18A . 0.9900 no
C18 H18B . 0.9900 no
C19 H19A . 0.9800 no
C19 H19B . 0.9800 no
C19 H19C . 0.9800 no
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_publ_flag
C2 C1 C4 C9 -21.7(2) yes
C12 C1 C4 C9 158.52(15) no
C2 C1 C4 C5 155.61(16) yes
C12 C1 C4 C5 -24.1(2) no
C9 C4 C5 C6 0.7(2) no
C1 C4 C5 C6 -176.76(15) no
C4 C5 C6 C7 0.2(3) no
C5 C6 C7 C8 -0.4(2) no
C5 C6 C7 C10 -179.58(15) no
C6 C7 C8 C9 -0.2(2) no
C10 C7 C8 C9 178.97(15) no
C7 C8 C9 C4 1.1(3) no
C5 C4 C9 C8 -1.3(2) no
C1 C4 C9 C8 176.17(15) no
C6 C7 C10 C11 101.36(19) no
C8 C7 C10 C11 -77.8(2) no
C2 C1 C12 C13 -39.3(2) yes
C4 C1 C12 C13 140.43(16) no
C2 C1 C12 C17 136.72(17) yes
C4 C1 C12 C17 -43.5(2) no
C17 C12 C13 C14 -0.4(2) no
C1 C12 C13 C14 175.78(14) no
C12 C13 C14 C15 -0.4(3) no
C13 C14 C15 C16 0.5(3) no
C13 C14 C15 C18 179.49(17) no
C14 C15 C16 C17 0.2(2) no
C18 C15 C16 C17 -178.78(16) no
C15 C16 C17 C12 -1.1(2) no
C13 C12 C17 C16 1.1(2) no
C1 C12 C17 C16 -175.03(14) no
C16 C15 C18 C19 171.39(16) no
C14 C15 C18 C19 -7.6(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101852686
