#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:18:41 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180499 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/68/7216890.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_7216890
loop_
_publ_author_name
'Anelli, Pier Lucio'
'Brocchetta, Marino'
'Maffezzoni, (the late) Costantino'
'Paoli, Paola'
'Rossi, Patrizia'
'Uggeri, Fulvio'
'Visigalli, Massimo'
_publ_section_title
;
 Syntheses and X-ray crystal structures of derivatives of
 2,2′,4,4′,6,6′-hexaiodobiphenyl
;
_journal_issue                   10
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1175
_journal_paper_doi               10.1039/b009666k
_journal_year                    2001
_chemical_formula_moiety         'C12 H4 I6 O4, 3(C3 H6 O)'
_chemical_formula_sum            'C21 H22 I6 O7'
_chemical_formula_weight         1147.79
_chemical_name_systematic
;
2,2'4,4'6,6'-hexaiodo-1,1'-biphenyl-3,3',5,5'-tetrol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 106.10(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.818(3)
_cell_length_b                   16.400(6)
_cell_length_c                   14.252(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     3103.0(15)
_computing_cell_refinement       'NONIUS CAD4'
_computing_data_collection       'NONIUS CAD4'
_computing_data_reduction        'NONIUS CAD4'
_computing_molecular_graphics    'ORTEP (Johnson, 1971)'
_computing_publication_material  'PARST (Nardelli, 1983)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et al 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'NONIUS CAD4'
_diffrn_measurement_method       'θ/2θ method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4259
_diffrn_reflns_theta_full        22.99
_diffrn_reflns_theta_max         22.99
_diffrn_reflns_theta_min         2.72
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    6.041
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   'Difabs by Walker and Stuart'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    2.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallepiped
_exptl_crystal_F_000             2088
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.848
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.076
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0634P)²+39.0124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1325
_reflns_number_gt                3163
_reflns_number_total             4063
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b009666k.txt
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7216890
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.75138(7) 0.45413(6) 0.66738(7) 0.0509(3) Uani 1 1 d .
I2 I 0.57224(8) 0.16773(7) 0.41707(8) 0.0599(3) Uani 1 1 d .
I3 I 0.38880(8) 0.27801(7) 0.73078(8) 0.0654(4) Uani 1 1 d .
I4 I 0.42552(8) 0.51125(7) 0.60477(7) 0.0637(3) Uani 1 1 d .
I5 I 0.59590(8) 0.61367(6) 1.02146(8) 0.0583(3) Uani 1 1 d .
I6 I 0.71126(8) 0.28882(6) 0.89230(7) 0.0558(3) Uani 1 1 d .
O1 O 0.7191(6) 0.3181(6) 0.5125(7) 0.046(2) Uani 1 1 d .
H1 H 0.7018 0.2983 0.4576 0.09(4) Uiso 1 1 calc R
O2 O 0.4313(8) 0.1786(7) 0.5487(8) 0.064(3) Uani 1 1 d .
H2 H 0.3922 0.1769 0.5826 0.09(4) Uiso 1 1 calc R
O3 O 0.4705(9) 0.6135(6) 0.8055(8) 0.063(3) Uani 1 1 d .
H3 H 0.4454 0.6214 0.7470 0.09(4) Uiso 1 1 calc R
O4 O 0.7041(8) 0.4376(7) 1.0206(7) 0.062(3) Uani 1 1 d .
H4 H 0.7189 0.4792 1.0535 0.09(4) Uiso 1 1 calc R
C1 C 0.6427(8) 0.3621(7) 0.6316(8) 0.032(3) Uani 1 1 d .
C2 C 0.6449(9) 0.3072(8) 0.5565(9) 0.039(3) Uani 1 1 d .
C3 C 0.5725(9) 0.2462(8) 0.5298(9) 0.040(3) Uani 1 1 d .
C4 C 0.4989(9) 0.2393(9) 0.5807(10) 0.047(4) Uani 1 1 d .
C5 C 0.4985(9) 0.2950(8) 0.6560(9) 0.038(3) Uani 1 1 d .
C6 C 0.5713(10) 0.3556(8) 0.6820(9) 0.039(3) Uani 1 1 d .
C7 C 0.5708(9) 0.4141(8) 0.7641(9) 0.039(3) Uani 1 1 d .
C8 C 0.5163(9) 0.4854(8) 0.7436(10) 0.042(3) Uani 1 1 d .
C9 C 0.5227(10) 0.5421(9) 0.8185(11) 0.047(3) Uani 1 1 d .
C10 C 0.5872(9) 0.5276(8) 0.9107(10) 0.043(3) Uani 1 1 d .
C11 C 0.6418(9) 0.4570(8) 0.9313(9) 0.038(3) Uani 1 1 d .
C12 C 0.6329(9) 0.3998(7) 0.8571(9) 0.034(3) Uani 1 1 d .
C20 C 0.2697(17) 0.2376(12) 0.2884(16) 0.086(6) Uani 1 1 d .
O20 O 0.2141(10) 0.1962(7) 0.3244(8) 0.072(3) Uani 1 1 d .
C21 C 0.3258(15) 0.3069(12) 0.3419(15) 0.082(5) Uani 1 1 d .
C22 C 0.269(3) 0.2218(16) 0.1807(18) 0.155(13) Uani 1 1 d .
C30 C 0.844(3) 0.524(2) 0.255(3) 0.19(2) Uani 1 1 d .
O30 O 0.758(2) 0.4875(13) 0.2131(13) 0.164(8) Uani 1 1 d .
C31 C 0.852(2) 0.506(2) 0.367(2) 0.149(11) Uani 1 1 d .
C32 C 0.899(4) 0.564(3) 0.226(5) 0.34(5) Uani 1 1 d .
C40 C 0.0738(16) 0.3947(14) 0.1316(17) 0.090(6) Uani 1 1 d .
O40 O 0.0861(12) 0.4107(10) 0.2163(14) 0.110(5) Uani 1 1 d .
C41 C -0.001(2) 0.335(2) 0.074(3) 0.192(16) Uani 1 1 d .
C42 C 0.135(2) 0.437(2) 0.074(2) 0.160(13) Uani 1 1 d .
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
C6 C1 C2 121.1(11)
C6 C1 I1 120.0(9)
C2 C1 I1 118.9(9)
O1 C2 C3 123.2(12)
O1 C2 C1 116.5(11)
C3 C2 C1 120.3(12)
C2 C3 C4 118.9(12)
C2 C3 I2 120.6(10)
C4 C3 I2 120.5(10)
O2 C4 C3 114.5(13)
O2 C4 C5 125.7(13)
C3 C4 C5 119.8(12)
C6 C5 C4 120.7(11)
C6 C5 I3 122.1(9)
C4 C5 I3 117.2(9)
C1 C6 C5 119.2(11)
C1 C6 C7 120.8(12)
C5 C6 C7 120.0(11)
C8 C7 C12 120.2(12)
C8 C7 C6 119.6(11)
C12 C7 C6 119.9(12)
C7 C8 C9 119.2(12)
C7 C8 I4 121.8(10)
C9 C8 I4 119.1(10)
O3 C9 C10 116.9(12)
O3 C9 C8 123.3(13)
C10 C9 C8 119.8(13)
C11 C10 C9 121.3(13)
C11 C10 I5 119.6(10)
C9 C10 I5 119.0(10)
O4 C11 C10 124.5(12)
O4 C11 C12 116.8(12)
C10 C11 C12 118.6(11)
C7 C12 C11 120.9(11)
C7 C12 I6 121.0(9)
C11 C12 I6 118.0(9)
O20 C20 C21 120.7(19)
O20 C20 C22 119(2)
C21 C20 C22 120(2)
C32 C30 O30 133(5)
C32 C30 C31 127(4)
O30 C30 C31 100(4)
O40 C40 C41 125(3)
O40 C40 C42 121(2)
C41 C40 C42 114(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.089(12)
I2 C3 2.057(14)
I3 C5 2.099(13)
I4 C8 2.072(13)
I5 C10 2.096(14)
I6 C12 2.106(11)
O1 C2 1.353(15)
O2 C4 1.354(16)
O3 C9 1.361(16)
O4 C11 1.361(15)
C1 C6 1.376(17)
C1 C2 1.405(18)
C2 C3 1.392(18)
C3 C4 1.408(19)
C4 C5 1.411(19)
C5 C6 1.390(18)
C6 C7 1.515(18)
C7 C8 1.377(18)
C7 C12 1.385(17)
C8 C9 1.399(19)
C9 C10 1.388(19)
C10 C11 1.368(18)
C11 C12 1.394(17)
C20 O20 1.24(2)
C20 C21 1.47(3)
C20 C22 1.55(3)
C30 C32 1.17(6)
C30 O30 1.31(4)
C30 C31 1.59(5)
C40 O40 1.20(2)
C40 C41 1.50(3)
C40 C42 1.50(3)
