#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/94/2229425.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_2229425
loop_
_publ_author_name
'Shah, Kiramat'
'Raza Shah, M.'
'Ng, Seik Weng'
_publ_section_title
;
 4,4'-Bis[(E)-(2,3-diiodoprop-2-en-1-yl)oxy]biphenyl
;
_journal_coeditor_code           JH2264
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o568
_journal_paper_doi               10.1107/S1600536811003874
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H14 I4 O2'
_chemical_formula_moiety         'C18 H14 I4 O2'
_chemical_formula_sum            'C18 H14 I4 O2'
_chemical_formula_weight         769.89
_chemical_name_systematic
;
4,4'-Bis[(E)-(2,3-diiodoprop-2-en-1-yl)oxy]biphenyl
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.760(4)
_cell_angle_beta                 101.433(3)
_cell_angle_gamma                108.211(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0470(4)
_cell_length_b                   10.2267(4)
_cell_length_c                   11.3581(4)
_cell_measurement_reflns_used    5987
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.1718
_cell_measurement_theta_min      2.3888
_cell_volume                     1014.45(8)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8121
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    2.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         3.379
_refine_diff_density_min         -1.691
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0391P)²+2.8781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0788
_reflns_number_gt                4118
_reflns_number_total             4502
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2264.cif
_cod_data_source_block           I
_cod_original_cell_volume        1014.45(7)
_cod_database_code               2229425
_cod_database_fobs_code          2229425
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
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.52321(3) 0.89339(3) 0.77411(3) 0.02006(8) Uani d . 1 . .
I I2 0.05784(3) 0.47289(3) 0.70014(3) 0.02903(10) Uani d . 1 . .
I I3 0.69630(3) -0.38925(3) 0.56256(3) 0.02370(9) Uani d . 1 . .
I I4 1.15769(3) -0.03766(3) 0.91544(3) 0.02524(9) Uani d . 1 . .
O O1 0.5470(4) 0.7096(3) 0.9645(3) 0.0202(6) Uani d . 1 . .
O O2 0.8521(4) -0.0703(3) 0.5344(3) 0.0200(6) Uani d . 1 . .
C C1 0.2354(5) 0.6460(5) 0.6979(5) 0.0207(9) Uani d . 1 . .
H H1 0.2259 0.6735 0.6242 0.025 Uiso calc R 1 . .
C C2 0.3610(5) 0.7193(5) 0.7945(4) 0.0181(9) Uani d . 1 . .
C C3 0.3993(5) 0.7013(5) 0.9214(4) 0.0194(9) Uani d . 1 . .
H H3A 0.3862 0.7788 0.9867 0.023 Uiso calc R 1 . .
H H3B 0.3297 0.6046 0.9150 0.023 Uiso calc R 1 . .
C C4 0.5783(5) 0.5922(5) 0.9042(4) 0.0177(9) Uani d . 1 . .
C C5 0.7224(5) 0.6043(5) 0.9543(4) 0.0182(9) Uani d . 1 . .
H H5 0.7893 0.6881 1.0270 0.022 Uiso calc R 1 . .
C C6 0.7679(5) 0.4940(5) 0.8981(4) 0.0184(9) Uani d . 1 . .
H H6 0.8666 0.5044 0.9316 0.022 Uiso calc R 1 . .
C C7 0.6700(5) 0.3677(5) 0.7927(4) 0.0167(8) Uani d . 1 . .
C C8 0.5257(5) 0.3563(5) 0.7479(4) 0.0193(9) Uani d . 1 . .
H H8 0.4568 0.2704 0.6782 0.023 Uiso calc R 1 . .
C C9 0.4797(5) 0.4667(5) 0.8023(4) 0.0194(9) Uani d . 1 . .
H H9 0.3806 0.4559 0.7696 0.023 Uiso calc R 1 . .
C C10 0.7198(5) 0.2529(5) 0.7296(4) 0.0160(8) Uani d . 1 . .
C C11 0.6679(5) 0.1820(5) 0.5947(4) 0.0189(9) Uani d . 1 . .
H H11 0.5995 0.2077 0.5448 0.023 Uiso calc R 1 . .
C C12 0.7143(5) 0.0756(5) 0.5334(4) 0.0191(9) Uani d . 1 . .
H H12 0.6784 0.0294 0.4424 0.023 Uiso calc R 1 . .
C C13 0.8144(5) 0.0367(4) 0.6066(4) 0.0163(8) Uani d . 1 . .
C C14 0.8670(5) 0.1041(5) 0.7393(4) 0.0181(9) Uani d . 1 . .
H H14 0.9346 0.0775 0.7891 0.022 Uiso calc R 1 . .
C C15 0.8192(5) 0.2116(5) 0.7992(4) 0.0172(8) Uani d . 1 . .
H H15 0.8558 0.2579 0.8902 0.021 Uiso calc R 1 . .
C C16 0.9582(5) -0.1128(5) 0.6013(4) 0.0192(9) Uani d . 1 . .
H H16A 1.0423 -0.0230 0.6631 0.023 Uiso calc R 1 . .
H H16B 0.9961 -0.1666 0.5386 0.023 Uiso calc R 1 . .
C C17 0.8964(5) -0.2085(5) 0.6726(4) 0.0172(8) Uani d . 1 . .
C C18 0.9551(5) -0.1992(5) 0.7908(4) 0.0201(9) Uani d . 1 . .
H H18 0.9018 -0.2705 0.8211 0.024 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
C4 O1 C3 . . 118.0(3) ?
C13 O2 C16 . . 117.6(3) ?
C2 C1 I2 . . 123.3(4) ?
C2 C1 H1 . . 118.3 ?
I2 C1 H1 . . 118.3 ?
C1 C2 C3 . . 128.2(4) ?
C1 C2 I1 . . 117.0(3) ?
C3 C2 I1 . . 114.7(3) ?
O1 C3 C2 . . 113.8(4) ?
O1 C3 H3A . . 108.8 ?
C2 C3 H3A . . 108.8 ?
O1 C3 H3B . . 108.8 ?
C2 C3 H3B . . 108.8 ?
H3A C3 H3B . . 107.7 ?
O1 C4 C9 . . 125.3(4) ?
O1 C4 C5 . . 115.2(4) ?
C9 C4 C5 . . 119.5(4) ?
C6 C5 C4 . . 120.2(4) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C7 . . 120.9(4) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
C8 C7 C6 . . 117.5(4) ?
C8 C7 C10 . . 121.5(4) ?
C6 C7 C10 . . 121.0(4) ?
C9 C8 C7 . . 122.0(4) ?
C9 C8 H8 . . 119.0 ?
C7 C8 H8 . . 119.0 ?
C4 C9 C8 . . 119.8(4) ?
C4 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C15 C10 C11 . . 117.5(4) ?
C15 C10 C7 . . 122.1(4) ?
C11 C10 C7 . . 120.4(4) ?
C12 C11 C10 . . 121.5(4) ?
C12 C11 H11 . . 119.3 ?
C10 C11 H11 . . 119.3 ?
C11 C12 C13 . . 119.5(4) ?
C11 C12 H12 . . 120.2 ?
C13 C12 H12 . . 120.2 ?
C14 C13 O2 . . 125.7(4) ?
C14 C13 C12 . . 120.3(4) ?
O2 C13 C12 . . 114.0(4) ?
C13 C14 C15 . . 119.2(4) ?
C13 C14 H14 . . 120.4 ?
C15 C14 H14 . . 120.4 ?
C10 C15 C14 . . 122.0(4) ?
C10 C15 H15 . . 119.0 ?
C14 C15 H15 . . 119.0 ?
O2 C16 C17 . . 113.0(4) ?
O2 C16 H16A . . 109.0 ?
C17 C16 H16A . . 109.0 ?
O2 C16 H16B . . 109.0 ?
C17 C16 H16B . . 109.0 ?
H16A C16 H16B . . 107.8 ?
C18 C17 C16 . . 128.5(4) ?
C18 C17 I3 . . 116.8(3) ?
C16 C17 I3 . . 114.6(3) ?
C17 C18 I4 . . 124.2(4) ?
C17 C18 H18 . . 117.9 ?
I4 C18 H18 . . 117.9 ?
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
I1 C2 . 2.107(4) ?
I2 C1 . 2.094(4) ?
I3 C17 . 2.109(4) ?
I4 C18 . 2.089(5) ?
O1 C4 . 1.372(5) ?
O1 C3 . 1.435(6) ?
O2 C13 . 1.381(5) ?
O2 C16 . 1.432(5) ?
C1 C2 . 1.331(7) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.493(6) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C9 . 1.383(6) ?
C4 C5 . 1.399(6) ?
C5 C6 . 1.392(6) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.403(6) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.395(6) ?
C7 C10 . 1.482(6) ?
C8 C9 . 1.389(6) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 C15 . 1.390(6) ?
C10 C11 . 1.410(6) ?
C11 C12 . 1.386(6) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.400(6) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.386(6) ?
C14 C15 . 1.398(6) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 C17 . 1.500(6) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.319(6) ?
C18 H18 . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
I2 C1 C2 C3 . . . . -3.1(7) ?
I2 C1 C2 I1 . . . . -178.41(19) ?
C4 O1 C3 C2 . . . . -73.4(5) ?
C1 C2 C3 O1 . . . . 139.5(5) ?
I1 C2 C3 O1 . . . . -45.1(4) ?
C3 O1 C4 C9 . . . . 1.6(6) ?
C3 O1 C4 C5 . . . . -177.3(4) ?
O1 C4 C5 C6 . . . . -177.9(4) ?
C9 C4 C5 C6 . . . . 3.1(6) ?
C4 C5 C6 C7 . . . . -1.5(7) ?
C5 C6 C7 C8 . . . . -0.9(6) ?
C5 C6 C7 C10 . . . . 177.6(4) ?
C6 C7 C8 C9 . . . . 1.8(7) ?
C10 C7 C8 C9 . . . . -176.8(4) ?
O1 C4 C9 C8 . . . . 178.9(4) ?
C5 C4 C9 C8 . . . . -2.3(7) ?
C7 C8 C9 C4 . . . . -0.2(7) ?
C8 C7 C10 C15 . . . . -143.3(4) ?
C6 C7 C10 C15 . . . . 38.2(6) ?
C8 C7 C10 C11 . . . . 37.3(6) ?
C6 C7 C10 C11 . . . . -141.2(4) ?
C15 C10 C11 C12 . . . . -0.3(7) ?
C7 C10 C11 C12 . . . . 179.2(4) ?
C10 C11 C12 C13 . . . . 0.3(7) ?
C16 O2 C13 C14 . . . . -2.1(6) ?
C16 O2 C13 C12 . . . . 177.8(4) ?
C11 C12 C13 C14 . . . . -0.1(7) ?
C11 C12 C13 O2 . . . . -179.9(4) ?
O2 C13 C14 C15 . . . . 179.6(4) ?
C12 C13 C14 C15 . . . . -0.2(6) ?
C11 C10 C15 C14 . . . . 0.0(6) ?
C7 C10 C15 C14 . . . . -179.5(4) ?
C13 C14 C15 C10 . . . . 0.3(7) ?
C13 O2 C16 C17 . . . . 74.9(5) ?
O2 C16 C17 C18 . . . . -135.0(5) ?
O2 C16 C17 I3 . . . . 49.6(4) ?
C16 C17 C18 I4 . . . . 1.3(7) ?
I3 C17 C18 I4 . . . . 176.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656534
