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#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/87/7058771.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_7058771
loop_
_publ_author_name
'Hayashi, Satoko'
'Uegaito, Manabu'
'Nishide, Taro'
'Tanaka, Eiichiro'
'Nakanishi, Waro'
'Sasamori, Takahiro'
'Tokitoh, Norihiro'
'Minoura, Mao'
_publ_section_title
;
 Nature of the E⋯E′ interactions (E, E′ = O, S, Se,
 and Te) at naphthalene 1,8-positions with fine details of the structures:
 experimental and theoretical investigations
;
_journal_issue                   36
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14224
_journal_paper_doi               10.1039/C9NJ02198A
_journal_volume                  43
_journal_year                    2019
_chemical_formula_sum            'C22 H16 O Te'
_chemical_formula_weight         423.95
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-07-25 deposited with the CCDC.    2019-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                91.7130(10)
_cell_angle_beta                 113.071(6)
_cell_angle_gamma                117.707(5)
_cell_formula_units_Z            2
_cell_length_a                   9.529(4)
_cell_length_b                   10.002(5)
_cell_length_c                   11.385(5)
_cell_measurement_reflns_used    2942
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      31.18
_cell_measurement_theta_min      2.52
_cell_volume                     853.3(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.831
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.831
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5359
_diffrn_reflns_point_group_measured_fraction_full 0.831
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.596
_diffrn_source                   'Mo K\a'
_exptl_absorpt_coefficient_mu    1.747
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.673
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0284
_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)+(0.0601P)²+1.0124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3224
_reflns_number_total             3279
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj02198a2.cif
_cod_data_source_block           3c_PhO-PhTe-Nap
_cod_depositor_comments
'Adding full bibliography for 7058768--7058773.cif.'
_cod_database_code               7058771
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.732
_shelx_estimated_absorpt_t_max   0.902
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Te1 Te 0.78845(2) 0.59930(2) 0.06472(2) 0.01391(11) Uani 1 1 d . .
O4 O 1.0470(3) 0.7813(3) -0.0071(2) 0.0208(4) Uani 1 1 d . .
C3 C 1.5338(4) 0.9044(3) 0.3071(3) 0.0164(5) Uani 1 1 d . .
H3 H 1.6450 0.9352 0.3804 0.020 Uiso 1 1 calc R U
C5 C 0.6470(4) 0.5003(3) 0.1753(3) 0.0141(5) Uani 1 1 d . .
C6 C 1.2073(4) 0.7812(3) 0.2121(3) 0.0121(5) Uani 1 1 d . .
C7 C 1.0286(4) 0.8043(3) -0.1316(3) 0.0148(5) Uani 1 1 d . .
C8 C 1.3751(4) 0.8290(3) 0.3215(3) 0.0130(5) Uani 1 1 d . .
C9 C 0.6148(4) 0.5917(3) 0.2437(3) 0.0163(5) Uani 1 1 d . .
H9 H 0.6632 0.6995 0.2461 0.020 Uiso 1 1 calc R U
C10 C 1.0637(4) 0.6767(3) 0.3506(3) 0.0147(5) Uani 1 1 d . .
H10 H 0.9592 0.6248 0.3620 0.018 Uiso 1 1 calc R U
C11 C 1.3838(4) 0.8016(3) 0.4451(3) 0.0157(5) Uani 1 1 d . .
H11 H 1.4956 0.8338 0.5183 0.019 Uiso 1 1 calc R U
C12 C 1.2094(4) 0.8186(3) 0.0919(3) 0.0134(5) Uani 1 1 d . .
C13 C 1.2308(4) 0.7287(3) 0.4588(3) 0.0158(5) Uani 1 1 d . .
H13 H 1.2377 0.7130 0.5423 0.019 Uiso 1 1 calc R U
C14 C 0.9930(4) 0.6866(3) -0.2261(3) 0.0185(6) Uani 1 1 d . .
H14 H 0.9916 0.5952 -0.2045 0.022 Uiso 1 1 calc R U
C15 C 0.4709(4) 0.2756(3) 0.2354(3) 0.0168(5) Uani 1 1 d . .
H15 H 0.4202 0.1673 0.2315 0.020 Uiso 1 1 calc R U
C16 C 1.3640(4) 0.8905(3) 0.0798(3) 0.0159(5) Uani 1 1 d . .
H16 H 1.3607 0.9115 -0.0017 0.019 Uiso 1 1 calc R U
C17 C 0.9602(4) 0.8388(4) -0.3847(3) 0.0178(5) Uani 1 1 d . .
H17 H 0.9358 0.8503 -0.4718 0.021 Uiso 1 1 calc R U
C18 C 0.5758(4) 0.3420(3) 0.1725(3) 0.0158(5) Uani 1 1 d . .
H18 H 0.5991 0.2796 0.1274 0.019 Uiso 1 1 calc R U
C19 C 0.5118(4) 0.5253(4) 0.3084(3) 0.0182(5) Uani 1 1 d . .
H19 H 0.4908 0.5881 0.3554 0.022 Uiso 1 1 calc R U
C20 C 0.9971(4) 0.9555(3) -0.2884(3) 0.0188(6) Uani 1 1 d . .
H20 H 0.9986 1.0471 -0.3099 0.023 Uiso 1 1 calc R U
C21 C 1.5283(4) 0.9331(4) 0.1893(3) 0.0174(5) Uani 1 1 d . .
H21 H 1.6351 0.9818 0.1808 0.021 Uiso 1 1 calc R U
C22 C 0.9591(4) 0.7050(4) -0.3533(3) 0.0202(6) Uani 1 1 d . .
H22 H 0.9352 0.6258 -0.4190 0.024 Uiso 1 1 calc R U
C24 C 1.0480(4) 0.6997(3) 0.2274(3) 0.0118(5) Uani 1 1 d . .
C27 C 0.4398(4) 0.3675(4) 0.3044(3) 0.0179(5) Uani 1 1 d . .
H27 H 0.3695 0.3223 0.3486 0.022 Uiso 1 1 calc R U
C28 C 1.0318(4) 0.9393(3) -0.1608(3) 0.0182(6) Uani 1 1 d . .
H28 H 1.0572 1.0191 -0.0948 0.022 Uiso 1 1 calc R U
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Te Te -0.5308 1.6751 '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
C24 Te1 C5 95.73(11)
C12 O4 C7 120.6(2)
C21 C3 C8 120.9(3)
C21 C3 H3 119.6
C8 C3 H3 119.6
C9 C5 C18 119.6(2)
C9 C5 Te1 119.7(2)
C18 C5 Te1 120.5(2)
C8 C6 C12 116.8(2)
C8 C6 C24 119.2(2)
C12 C6 C24 124.0(2)
C14 C7 C28 121.7(3)
C14 C7 O4 119.3(3)
C28 C7 O4 118.8(3)
C11 C8 C3 120.0(3)
C11 C8 C6 119.9(3)
C3 C8 C6 120.1(3)
C19 C9 C5 120.1(3)
C19 C9 H9 119.9
C5 C9 H9 119.9
C24 C10 C13 121.5(3)
C24 C10 H10 119.3
C13 C10 H10 119.3
C13 C11 C8 120.0(3)
C13 C11 H11 120.0
C8 C11 H11 120.0
O4 C12 C16 123.2(2)
O4 C12 C6 114.7(2)
C16 C12 C6 122.1(3)
C11 C13 C10 120.7(3)
C11 C13 H13 119.6
C10 C13 H13 119.6
C7 C14 C22 118.8(3)
C7 C14 H14 120.6
C22 C14 H14 120.6
C18 C15 C27 120.2(3)
C18 C15 H15 119.9
C27 C15 H15 119.9
C12 C16 C21 119.8(3)
C12 C16 H16 120.1
C21 C16 H16 120.1
C20 C17 C22 119.9(3)
C20 C17 H17 120.0
C22 C17 H17 120.0
C15 C18 C5 120.1(2)
C15 C18 H18 119.9
C5 C18 H18 119.9
C27 C19 C9 120.2(3)
C27 C19 H19 119.9
C9 C19 H19 119.9
C17 C20 C28 120.4(3)
C17 C20 H20 119.8
C28 C20 H20 119.8
C3 C21 C16 120.3(3)
C3 C21 H21 119.9
C16 C21 H21 119.9
C17 C22 C14 120.4(3)
C17 C22 H22 119.8
C14 C22 H22 119.8
C10 C24 C6 118.7(2)
C10 C24 Te1 119.0(2)
C6 C24 Te1 122.21(19)
C19 C27 C15 119.8(3)
C19 C27 H27 120.1
C15 C27 H27 120.1
C7 C28 C20 118.8(3)
C7 C28 H28 120.6
C20 C28 H28 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Te1 C24 2.132(3)
Te1 C5 2.132(3)
O4 C12 1.370(3)
O4 C7 1.399(3)
C3 C21 1.366(4)
C3 C8 1.423(4)
C3 H3 0.9500
C5 C9 1.393(4)
C5 C18 1.397(4)
C6 C8 1.424(4)
C6 C12 1.435(4)
C6 C24 1.437(4)
C7 C14 1.387(4)
C7 C28 1.389(4)
C8 C11 1.420(4)
C9 C19 1.392(4)
C9 H9 0.9500
C10 C24 1.389(4)
C10 C13 1.407(4)
C10 H10 0.9500
C11 C13 1.370(4)
C11 H11 0.9500
C12 C16 1.373(4)
C13 H13 0.9500
C14 C22 1.393(4)
C14 H14 0.9500
C15 C18 1.388(4)
C15 C27 1.393(4)
C15 H15 0.9500
C16 C21 1.415(4)
C16 H16 0.9500
C17 C20 1.388(4)
C17 C22 1.392(4)
C17 H17 0.9500
C18 H18 0.9500
C19 C27 1.389(4)
C19 H19 0.9500
C20 C28 1.391(4)
C20 H20 0.9500
C21 H21 0.9500
C22 H22 0.9500
C27 H27 0.9500
C28 H28 0.9500
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
C12 O4 C7 C14 87.8(3)
C12 O4 C7 C28 -97.6(3)
C21 C3 C8 C11 -179.4(3)
C21 C3 C8 C6 0.5(4)
C12 C6 C8 C11 177.4(2)
C24 C6 C8 C11 -2.6(4)
C12 C6 C8 C3 -2.5(3)
C24 C6 C8 C3 177.5(2)
C18 C5 C9 C19 -0.2(4)
Te1 C5 C9 C19 175.5(2)
C3 C8 C11 C13 -179.9(3)
C6 C8 C11 C13 0.2(4)
C7 O4 C12 C16 5.2(4)
C7 O4 C12 C6 -176.8(2)
C8 C6 C12 O4 -175.1(2)
C24 C6 C12 O4 4.9(4)
C8 C6 C12 C16 3.0(4)
C24 C6 C12 C16 -177.0(2)
C8 C11 C13 C10 1.6(4)
C24 C10 C13 C11 -1.1(4)
C28 C7 C14 C22 -0.2(5)
O4 C7 C14 C22 174.3(3)
O4 C12 C16 C21 176.4(3)
C6 C12 C16 C21 -1.5(4)
C27 C15 C18 C5 -1.5(4)
C9 C5 C18 C15 1.2(4)
Te1 C5 C18 C15 -174.4(2)
C5 C9 C19 C27 -0.4(4)
C22 C17 C20 C28 -0.4(5)
C8 C3 C21 C16 1.1(4)
C12 C16 C21 C3 -0.7(4)
C20 C17 C22 C14 0.7(5)
C7 C14 C22 C17 -0.4(5)
C13 C10 C24 C6 -1.3(4)
C13 C10 C24 Te1 174.5(2)
C8 C6 C24 C10 3.0(4)
C12 C6 C24 C10 -176.9(2)
C8 C6 C24 Te1 -172.61(18)
C12 C6 C24 Te1 7.4(3)
C9 C19 C27 C15 0.0(4)
C18 C15 C27 C19 0.9(4)
C14 C7 C28 C20 0.4(5)
O4 C7 C28 C20 -174.1(3)
C17 C20 C28 C7 -0.1(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101371938
