#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226697.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_2226697
loop_
_publ_author_name
'Liu, Ying'
'Wang, Leyong'
'Wang, Jingjing'
'Liu, Li'
'Teng, Mingyu'
_publ_section_title
;
 1,8-Bis(benzyloxy)-3,6-diiodonaphthalene
;
_journal_coeditor_code           TK2673
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1577
_journal_paper_doi               10.1107/S1600536810019355
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C24 H18 I2 O2'
_chemical_formula_moiety         'C24 H18 I2 O2'
_chemical_formula_sum            'C24 H18 I2 O2'
_chemical_formula_weight         592.18
_chemical_name_systematic
;
1,8-Bis(benzyloxy)-3,6-diiodonaphthalene
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 118.680(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.222(4)
_cell_length_b                   5.5684(8)
_cell_length_c                   27.445(4)
_cell_measurement_reflns_used    3618
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.62
_cell_volume                     4186.1(10)
_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      291(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10700
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    3.022
_exptl_absorpt_correction_T_max  0.5561
_exptl_absorpt_correction_T_min  0.4850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.860
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0522
_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)+(0.04P)²+1.22P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                2679
_reflns_number_total             4111
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            tk2673.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2226697
_cod_database_fobs_code          2226697
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
I I1BA 0.532315(16) -0.52925(9) 0.184014(16) 0.05132(16) Uani d . 1 . .
I I2BA 0.419035(16) 0.51148(9) -0.067214(17) 0.05151(15) Uani d . 1 . .
O O2BA 0.35208(14) 0.3984(7) 0.08149(16) 0.0368(9) Uani d . 1 . .
O O1BA 0.39304(14) 0.1087(7) 0.16410(16) 0.0363(9) Uani d . 1 . .
C C7BA 0.3862(2) 0.4364(11) 0.0199(2) 0.0382(14) Uani d . 1 . .
H H7AA 0.3664 0.5679 0.0024 0.046 Uiso calc R 1 . .
C C1BA 0.42086(19) 0.0189(11) 0.1420(2) 0.0324(12) Uani d . 1 . .
C C18A 0.31949(19) 0.5945(10) 0.0502(2) 0.0328(12) Uani d . 1 . .
H H18A 0.3029 0.5558 0.0109 0.039 Uiso calc R 1 . .
H H18B 0.3382 0.7401 0.0554 0.039 Uiso calc R 1 . .
C C9BA 0.41640(19) 0.1355(11) 0.0930(2) 0.0320(12) Uani d . 1 . .
C C8BA 0.38423(18) 0.3302(10) 0.0639(2) 0.0295(12) Uani d . 1 . .
C C3BA 0.4817(2) -0.2471(10) 0.1437(2) 0.0344(13) Uani d . 1 . .
C C12A 0.36459(19) 0.1100(11) 0.2302(2) 0.0319(12) Uani d . 1 . .
C C16A 0.3090(2) 0.4135(12) 0.2268(2) 0.0433(15) Uani d . 1 . .
H H16A 0.2918 0.5539 0.2108 0.052 Uiso calc R 1 . .
C C24A 0.28382(19) 0.8405(11) 0.0981(2) 0.0327(13) Uani d . 1 . .
H H24A 0.3086 0.9526 0.1070 0.039 Uiso calc R 1 . .
C C10A 0.4473(2) 0.0466(11) 0.0720(2) 0.0387(14) Uani d . 1 . .
C C20A 0.2453(2) 0.4703(11) 0.0574(2) 0.0398(14) Uani d . 1 . .
H H20A 0.2444 0.3288 0.0389 0.048 Uiso calc R 1 . .
C C5BA 0.4469(2) 0.1581(13) 0.0250(3) 0.0464(16) Uani d . 1 . .
H H5AA 0.4667 0.0990 0.0111 0.056 Uiso calc R 1 . .
C C23A 0.2477(2) 0.8811(13) 0.1134(3) 0.0479(16) Uani d . 1 . .
H H23A 0.2486 1.0209 0.1324 0.057 Uiso calc R 1 . .
C C17A 0.3387(2) 0.3144(11) 0.2077(2) 0.0351(13) Uani d . 1 . .
H H17A 0.3411 0.3891 0.1788 0.042 Uiso calc R 1 . .
C C21A 0.2097(2) 0.5140(13) 0.0718(2) 0.0433(14) Uani d . 1 . .
H H21A 0.1843 0.4052 0.0619 0.052 Uiso calc R 1 . .
C C19A 0.2827(2) 0.6336(11) 0.0698(2) 0.0338(13) Uani d . 1 . .
C C4BA 0.4804(2) -0.1452(11) 0.0988(2) 0.0357(13) Uani d . 1 . .
H H4AA 0.5009 -0.1993 0.0854 0.043 Uiso calc R 1 . .
C C14A 0.3307(2) 0.1026(12) 0.2930(3) 0.0421(15) Uani d . 1 . .
H H14A 0.3280 0.0315 0.3221 0.051 Uiso calc R 1 . .
C C22A 0.2115(2) 0.7196(11) 0.1009(2) 0.0370(14) Uani d . 1 . .
H H22A 0.1879 0.7468 0.1119 0.044 Uiso calc R 1 . .
C C6BA 0.4180(2) 0.3482(12) 0.0009(2) 0.0397(14) Uani d . 1 . .
C C2BA 0.4528(2) -0.1716(10) 0.1661(2) 0.0331(12) Uani d . 1 . .
H H2AA 0.4547 -0.2482 0.1972 0.040 Uiso calc R 1 . .
C C11A 0.3975(2) -0.0106(11) 0.2126(2) 0.0341(12) Uani d . 1 . .
H H11A 0.4310 -0.0026 0.2422 0.041 Uiso calc R 1 . .
H H11B 0.3885 -0.1783 0.2044 0.041 Uiso calc R 1 . .
C C15A 0.3048(2) 0.3079(13) 0.2684(3) 0.0470(16) Uani d . 1 . .
H H15A 0.2842 0.3741 0.2806 0.056 Uiso calc R 1 . .
C C13A 0.3607(2) 0.0025(13) 0.2745(3) 0.0469(15) Uani d . 1 . .
H H13A 0.3784 -0.1359 0.2911 0.056 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C8BA O2BA C18A . . 115.2(4) ?
C1BA O1BA C11A . . 116.2(4) ?
C8BA C7BA C6BA . . 120.7(5) ?
C8BA C7BA H7AA . . 119.6 ?
C6BA C7BA H7AA . . 119.6 ?
O1BA C1BA C2BA . . 122.2(5) ?
O1BA C1BA C9BA . . 116.8(5) ?
C2BA C1BA C9BA . . 121.0(5) ?
O2BA C18A C19A . . 109.6(4) ?
O2BA C18A H18A . . 109.7 ?
C19A C18A H18A . . 109.7 ?
O2BA C18A H18B . . 109.7 ?
C19A C18A H18B . . 109.7 ?
H18A C18A H18B . . 108.2 ?
C10A C9BA C8BA . . 117.7(5) ?
C10A C9BA C1BA . . 116.1(5) ?
C8BA C9BA C1BA . . 126.2(5) ?
O2BA C8BA C7BA . . 123.0(5) ?
O2BA C8BA C9BA . . 116.9(5) ?
C7BA C8BA C9BA . . 120.2(5) ?
C4BA C3BA C2BA . . 122.9(5) ?
C4BA C3BA I1BA . . 118.7(4) ?
C2BA C3BA I1BA . . 118.4(4) ?
C17A C12A C13A . . 117.9(5) ?
C17A C12A C11A . . 125.6(5) ?
C13A C12A C11A . . 116.5(5) ?
C15A C16A C17A . . 120.3(6) ?
C15A C16A H16A . . 119.9 ?
C17A C16A H16A . . 119.9 ?
C19A C24A C23A . . 119.9(6) ?
C19A C24A H24A . . 120.1 ?
C23A C24A H24A . . 120.1 ?
C4BA C10A C5BA . . 119.0(6) ?
C4BA C10A C9BA . . 121.0(5) ?
C5BA C10A C9BA . . 120.0(6) ?
C21A C20A C19A . . 121.1(6) ?
C21A C20A H20A . . 119.5 ?
C19A C20A H20A . . 119.5 ?
C6BA C5BA C10A . . 120.2(6) ?
C6BA C5BA H5AA . . 119.9 ?
C10A C5BA H5AA . . 119.9 ?
C22A C23A C24A . . 120.9(6) ?
C22A C23A H23A . . 119.6 ?
C24A C23A H23A . . 119.6 ?
C12A C17A C16A . . 121.5(6) ?
C12A C17A H17A . . 119.2 ?
C16A C17A H17A . . 119.2 ?
C20A C21A C22A . . 120.2(6) ?
C20A C21A H21A . . 119.9 ?
C22A C21A H21A . . 119.9 ?
C24A C19A C20A . . 118.5(5) ?
C24A C19A C18A . . 120.4(5) ?
C20A C19A C18A . . 121.0(5) ?
C3BA C4BA C10A . . 119.3(5) ?
C3BA C4BA H4AA . . 120.4 ?
C10A C4BA H4AA . . 120.4 ?
C15A C14A C13A . . 119.8(6) ?
C15A C14A H14A . . 120.1 ?
C13A C14A H14A . . 120.1 ?
C23A C22A C21A . . 119.5(6) ?
C23A C22A H22A . . 120.2 ?
C21A C22A H22A . . 120.2 ?
C5BA C6BA C7BA . . 121.1(6) ?
C5BA C6BA I2BA . . 119.3(5) ?
C7BA C6BA I2BA . . 119.6(4) ?
C3BA C2BA C1BA . . 119.7(5) ?
C3BA C2BA H2AA . . 120.1 ?
C1BA C2BA H2AA . . 120.1 ?
O1BA C11A C12A . . 108.6(5) ?
O1BA C11A H11A . . 110.0 ?
C12A C11A H11A . . 110.0 ?
O1BA C11A H11B . . 110.0 ?
C12A C11A H11B . . 110.0 ?
H11A C11A H11B . . 108.4 ?
C16A C15A C14A . . 120.5(6) ?
C16A C15A H15A . . 119.8 ?
C14A C15A H15A . . 119.8 ?
C14A C13A C12A . . 120.0(6) ?
C14A C13A H13A . . 120.0 ?
C12A C13A H13A . . 120.0 ?
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
I1BA C3BA . 2.124(6) ?
I2BA C6BA . 2.092(6) ?
O2BA C8BA . 1.361(6) ?
O2BA C18A . 1.458(6) ?
O1BA C1BA . 1.369(7) ?
O1BA C11A . 1.434(6) ?
C7BA C8BA . 1.371(8) ?
C7BA C6BA . 1.414(8) ?
C7BA H7AA . 0.9300 ?
C1BA C2BA . 1.387(8) ?
C1BA C9BA . 1.439(7) ?
C18A C19A . 1.499(7) ?
C18A H18A . 0.9700 ?
C18A H18B . 0.9700 ?
C9BA C10A . 1.430(8) ?
C9BA C8BA . 1.433(8) ?
C3BA C4BA . 1.338(8) ?
C3BA C2BA . 1.379(8) ?
C12A C17A . 1.361(8) ?
C12A C13A . 1.410(8) ?
C12A C11A . 1.489(8) ?
C16A C15A . 1.345(9) ?
C16A C17A . 1.381(8) ?
C16A H16A . 0.9300 ?
C24A C19A . 1.380(8) ?
C24A C23A . 1.397(8) ?
C24A H24A . 0.9300 ?
C10A C4BA . 1.421(8) ?
C10A C5BA . 1.425(8) ?
C20A C21A . 1.368(9) ?
C20A C19A . 1.387(8) ?
C20A H20A . 0.9300 ?
C5BA C6BA . 1.342(9) ?
C5BA H5AA . 0.9300 ?
C23A C22A . 1.354(9) ?
C23A H23A . 0.9300 ?
C17A H17A . 0.9300 ?
C21A C22A . 1.382(9) ?
C21A H21A . 0.9300 ?
C4BA H4AA . 0.9300 ?
C14A C15A . 1.376(9) ?
C14A C13A . 1.381(9) ?
C14A H14A . 0.9300 ?
C22A H22A . 0.9300 ?
C2BA H2AA . 0.9300 ?
C11A H11A . 0.9700 ?
C11A H11B . 0.9700 ?
C15A H15A . 0.9300 ?
C13A H13A . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C24A H24A O1BA 1_565 0.93 2.49 3.348(8) 154
C18A H18A Cg 7_565 0.97 2.77 3.513(5) 134
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
C11A O1BA C1BA C2BA . . . . -2.1(8) ?
C11A O1BA C1BA C9BA . . . . 179.4(5) ?
C8BA O2BA C18A C19A . . . . 174.0(5) ?
O1BA C1BA C9BA C10A . . . . 177.3(5) ?
C2BA C1BA C9BA C10A . . . . -1.2(8) ?
O1BA C1BA C9BA C8BA . . . . -2.7(8) ?
C2BA C1BA C9BA C8BA . . . . 178.8(6) ?
C18A O2BA C8BA C7BA . . . . -0.1(8) ?
C18A O2BA C8BA C9BA . . . . -179.1(5) ?
C6BA C7BA C8BA O2BA . . . . -175.7(5) ?
C6BA C7BA C8BA C9BA . . . . 3.3(9) ?
C10A C9BA C8BA O2BA . . . . 174.3(5) ?
C1BA C9BA C8BA O2BA . . . . -5.7(8) ?
C10A C9BA C8BA C7BA . . . . -4.7(8) ?
C1BA C9BA C8BA C7BA . . . . 175.3(5) ?
C8BA C9BA C10A C4BA . . . . 179.6(5) ?
C1BA C9BA C10A C4BA . . . . -0.3(8) ?
C8BA C9BA C10A C5BA . . . . 2.7(8) ?
C1BA C9BA C10A C5BA . . . . -177.3(5) ?
C4BA C10A C5BA C6BA . . . . -176.2(6) ?
C9BA C10A C5BA C6BA . . . . 0.8(9) ?
C19A C24A C23A C22A . . . . 0.2(9) ?
C13A C12A C17A C16A . . . . -0.8(9) ?
C11A C12A C17A C16A . . . . 180.0(6) ?
C15A C16A C17A C12A . . . . -0.3(9) ?
C19A C20A C21A C22A . . . . -2.2(9) ?
C23A C24A C19A C20A . . . . -0.1(8) ?
C23A C24A C19A C18A . . . . 176.4(5) ?
C21A C20A C19A C24A . . . . 1.1(9) ?
C21A C20A C19A C18A . . . . -175.3(5) ?
O2BA C18A C19A C24A . . . . 111.8(6) ?
O2BA C18A C19A C20A . . . . -71.8(6) ?
C2BA C3BA C4BA C10A . . . . -1.2(9) ?
I1BA C3BA C4BA C10A . . . . -179.0(4) ?
C5BA C10A C4BA C3BA . . . . 178.5(6) ?
C9BA C10A C4BA C3BA . . . . 1.5(9) ?
C24A C23A C22A C21A . . . . -1.2(9) ?
C20A C21A C22A C23A . . . . 2.2(9) ?
C10A C5BA C6BA C7BA . . . . -2.3(10) ?
C10A C5BA C6BA I2BA . . . . 179.0(5) ?
C8BA C7BA C6BA C5BA . . . . 0.3(10) ?
C8BA C7BA C6BA I2BA . . . . 179.0(4) ?
C4BA C3BA C2BA C1BA . . . . -0.4(9) ?
I1BA C3BA C2BA C1BA . . . . 177.4(4) ?
O1BA C1BA C2BA C3BA . . . . -176.8(5) ?
C9BA C1BA C2BA C3BA . . . . 1.7(8) ?
C1BA O1BA C11A C12A . . . . -179.6(4) ?
C17A C12A C11A O1BA . . . . -6.4(8) ?
C13A C12A C11A O1BA . . . . 174.3(5) ?
C17A C16A C15A C14A . . . . 1.2(10) ?
C13A C14A C15A C16A . . . . -0.8(10) ?
C15A C14A C13A C12A . . . . -0.3(10) ?
C17A C12A C13A C14A . . . . 1.1(9) ?
C11A C12A C13A C14A . . . . -179.6(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745165
2 PubChem 139079200
