#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/06/2220680.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_2220680
loop_
_publ_author_name
'Sonoda, Yoriko'
'Yoshida, Masaru'
'Goto, Midori'
_publ_section_title
;
 (Z,E,Z)-1,6-Di-1-naphthylhexa-1,3,5-triene
;
_journal_coeditor_code           AT2699
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o294
_journal_paper_doi               10.1107/S1600536809000592
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C26 H20'
_chemical_formula_moiety         'C26 H20'
_chemical_formula_sum            'C26 H20'
_chemical_formula_weight         332.42
_chemical_name_systematic
;
(Z,E,Z)-1,6-Di-1-naphthylhexa-1,3,5-triene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 96.535(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.0071(8)
_cell_length_b                   11.0709(17)
_cell_length_c                   16.110(3)
_cell_measurement_reflns_used    1467
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.123
_cell_measurement_theta_min      2.545
_cell_volume                     887.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      203(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating unit'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5367
_diffrn_reflns_theta_full        27.26
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1186
_diffrn_standards_number         51
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_correction_T_min  0.9103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0426
_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)+(0.0527P)²+0.1208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                1366
_reflns_number_total             2023
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2699.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2220680
_cod_database_fobs_code          2220680
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.0718(2) 0.18611(12) 0.28101(8) 0.0349(3) Uani d . 1 . .
C C2 0.2135(3) 0.10461(14) 0.33764(9) 0.0425(4) Uani d . 1 . .
H H2 0.3383 0.0511 0.3183 0.051 Uiso calc R 1 . .
C C3 0.1719(3) 0.10250(15) 0.42018(9) 0.0506(4) Uani d . 1 . .
H H3 0.2711 0.0489 0.4570 0.061 Uiso calc R 1 . .
C C4 -0.0171(3) 0.17947(16) 0.45017(9) 0.0536(4) Uani d . 1 . .
H H4 -0.0446 0.1773 0.5069 0.064 Uiso calc R 1 . .
C C5 -0.1600(3) 0.25694(15) 0.39761(9) 0.0501(4) Uani d . 1 . .
H H5 -0.2894 0.3068 0.4182 0.060 Uiso calc R 1 . .
C C6 -0.1188(3) 0.26465(13) 0.31206(8) 0.0399(3) Uani d . 1 . .
C C7 -0.2601(3) 0.34839(14) 0.25750(10) 0.0476(4) Uani d . 1 . .
H H7 -0.3870 0.4002 0.2776 0.057 Uiso calc R 1 . .
C C8 -0.2140(3) 0.35465(14) 0.17611(10) 0.0482(4) Uani d . 1 . .
H H8 -0.3063 0.4120 0.1406 0.058 Uiso calc R 1 . .
C C9 -0.0295(3) 0.27621(13) 0.14452(9) 0.0428(4) Uani d . 1 . .
H H9 -0.0016 0.2818 0.0879 0.051 Uiso calc R 1 . .
C C10 0.1111(3) 0.19160(13) 0.19424(8) 0.0369(3) Uani d . 1 . .
C C11 0.3027(3) 0.10910(13) 0.16049(8) 0.0411(3) Uani d . 1 . .
H H11 0.4733 0.1020 0.1911 0.049 Uiso calc R 1 . .
C C12 0.2587(3) 0.04314(13) 0.09057(8) 0.0407(3) Uani d . 1 . .
H H12 0.4052 -0.0023 0.0761 0.049 Uiso calc R 1 . .
C C13 0.0132(3) 0.03363(13) 0.03492(8) 0.0386(3) Uani d . 1 . .
H H13 -0.1374 0.0771 0.0483 0.046 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 C6 . . 118.04(13) ?
C2 C1 C10 . . 122.72(13) ?
C6 C1 C10 . . 119.24(12) ?
C3 C2 C1 . . 121.08(14) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C2 C3 C4 . . 120.56(15) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C5 C4 C3 . . 120.03(14) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 121.45(15) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C7 C6 C5 . . 121.78(14) ?
C7 C6 C1 . . 119.41(13) ?
C5 C6 C1 . . 118.81(14) ?
C8 C7 C6 . . 120.41(14) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C7 C8 C9 . . 120.61(14) ?
C7 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
C10 C9 C8 . . 121.66(13) ?
C10 C9 H9 . . 119.2 ?
C8 C9 H9 . . 119.2 ?
C9 C10 C1 . . 118.61(13) ?
C9 C10 C11 . . 121.32(13) ?
C1 C10 C11 . . 120.06(12) ?
C12 C11 C10 . . 126.65(12) ?
C12 C11 H11 . . 116.7 ?
C10 C11 H11 . . 116.7 ?
C11 C12 C13 . . 127.61(13) ?
C11 C12 H12 . . 116.2 ?
C13 C12 H12 . . 116.2 ?
C13 C13 C12 3 . 123.89(16) ?
C13 C13 H13 3 . 118.1 ?
C12 C13 H13 . . 118.1 ?
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 . 1.4153(19) ?
C1 C6 . 1.4232(19) ?
C1 C10 . 1.4350(18) ?
C2 C3 . 1.369(2) ?
C2 H2 . 0.9400 ?
C3 C4 . 1.400(2) ?
C3 H3 . 0.9400 ?
C4 C5 . 1.351(2) ?
C4 H4 . 0.9400 ?
C5 C6 . 1.419(2) ?
C5 H5 . 0.9400 ?
C6 C7 . 1.411(2) ?
C7 C8 . 1.359(2) ?
C7 H7 . 0.9400 ?
C8 C9 . 1.405(2) ?
C8 H8 . 0.9400 ?
C9 C10 . 1.3736(19) ?
C9 H9 . 0.9400 ?
C10 C11 . 1.4727(19) ?
C11 C12 . 1.3395(19) ?
C11 H11 . 0.9400 ?
C12 C13 . 1.4404(18) ?
C12 H12 . 0.9400 ?
C13 C13 3 1.343(3) ?
C13 H13 . 0.9400 ?
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
C6 C1 C2 C3 . . . . -1.0(2) ?
C10 C1 C2 C3 . . . . 179.57(13) ?
C1 C2 C3 C4 . . . . 1.4(2) ?
C2 C3 C4 C5 . . . . -0.1(2) ?
C3 C4 C5 C6 . . . . -1.5(2) ?
C4 C5 C6 C7 . . . . -177.64(14) ?
C4 C5 C6 C1 . . . . 1.9(2) ?
C2 C1 C6 C7 . . . . 178.92(12) ?
C10 C1 C6 C7 . . . . -1.60(19) ?
C2 C1 C6 C5 . . . . -0.66(18) ?
C10 C1 C6 C5 . . . . 178.82(12) ?
C5 C6 C7 C8 . . . . 179.19(14) ?
C1 C6 C7 C8 . . . . -0.4(2) ?
C6 C7 C8 C9 . . . . 1.4(2) ?
C7 C8 C9 C10 . . . . -0.4(2) ?
C8 C9 C10 C1 . . . . -1.6(2) ?
C8 C9 C10 C11 . . . . 179.55(13) ?
C2 C1 C10 C9 . . . . -178.01(13) ?
C6 C1 C10 C9 . . . . 2.54(18) ?
C2 C1 C10 C11 . . . . 0.90(19) ?
C6 C1 C10 C11 . . . . -178.55(12) ?
C9 C10 C11 C12 . . . . -48.6(2) ?
C1 C10 C11 C12 . . . . 132.53(15) ?
C10 C11 C12 C13 . . . . -3.0(2) ?
C11 C12 C13 C13 . . . 3 179.04(17) ?
