#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/16/4101602.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_4101602
loop_
_publ_author_name
'Rodriguez-Rodriguez, Cristina'
'Sanchez de Groot, Natalia'
'Rimola, Albert'
'Alvarez-Larena, Angel'
'Lloveras, Vega'
'Vidal-Gancedo, Jose'
'Ventura, Salvador'
'Vendrell, Josep'
'Sodupe, Mariona'
'Gonzalez-Duarte, Pilar'
_publ_section_title
;
 Design, Selection, and Characterization of Thioflavin-Based
 Intercalation Compounds with Metal Chelating Properties for
 Application in Alzheimer's Disease
;
_journal_issue                   4
_journal_name_full               'JOURNAL OF THE AMERICAN CHEMICAL SOCIETY'
_journal_page_first              1436
_journal_page_last               1451
_journal_paper_doi               10.1021/ja806062g
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C13 H8 I N O S'
_chemical_formula_weight         353.16
_chemical_name_systematic
;
2-(benzo[d]thiazol-2-yl)-4-iodophenol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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
_cell_angle_beta                 106.323(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7636(15)
_cell_length_b                   4.7515(5)
_cell_length_c                   18.0167(17)
_cell_measurement_reflns_used    1736
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      20.86
_cell_measurement_theta_min      2.39
_cell_volume                     1212.9(2)
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_collection       'SMART 5.6 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_structure_refinement  'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 8.13
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7911
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         1.44
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         310
_exptl_absorpt_coefficient_mu    2.793
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 2.05'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0422
_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)+(0.0466P)²+0.1310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                1973
_reflns_number_total             2982
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            reformated.cif
_cod_data_source_block           BTI
_cod_database_code               4101602
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
I4 I 1.02910(2) 0.67410(7) 0.133486(18) 0.07562(17) Uani 1 1 d . . .
S13 S 0.79178(8) -0.1215(2) -0.07041(6) 0.0544(3) Uani 1 1 d . . .
O1 O 0.6405(2) 0.1253(7) 0.11150(19) 0.0747(9) Uani 1 1 d . . .
H1 H 0.6256 0.0126 0.0756 0.112 Uiso 1 1 calc R . .
N11 N 0.6559(2) -0.1685(7) -0.00651(18) 0.0523(8) Uani 1 1 d . . .
C14 C 0.6990(3) -0.3455(7) -0.1131(2) 0.0508(10) Uani 1 1 d . . .
C2 C 0.7747(3) 0.1667(7) 0.0611(2) 0.0474(9) Uani 1 1 d . . .
C18 C 0.6060(3) -0.6741(9) -0.2013(2) 0.0628(12) Uani 1 1 d . . .
H18 H 0.5957 -0.7856 -0.2453 0.075 Uiso 1 1 calc R . .
C4 C 0.8969(3) 0.4911(8) 0.1247(2) 0.0525(10) Uani 1 1 d . . .
C12 C 0.7352(3) -0.0385(8) 0.0000(2) 0.0468(9) Uani 1 1 d . . .
C17 C 0.5412(3) -0.6798(9) -0.1581(3) 0.0641(12) Uani 1 1 d . . .
H17 H 0.4883 -0.7950 -0.1737 0.077 Uiso 1 1 calc R . .
C3 C 0.8614(3) 0.2929(8) 0.0680(2) 0.0511(10) Uani 1 1 d . . .
H3 H 0.8960 0.2434 0.0340 0.061 Uiso 1 1 calc R . .
C15 C 0.6337(3) -0.3486(8) -0.0702(2) 0.0490(9) Uani 1 1 d . . .
C5 C 0.8467(3) 0.5659(9) 0.1748(2) 0.0600(11) Uani 1 1 d . . .
H5 H 0.8709 0.7002 0.2128 0.072 Uiso 1 1 calc R . .
C19 C 0.6852(3) -0.5061(8) -0.1800(2) 0.0568(10) Uani 1 1 d . . .
H19 H 0.7279 -0.5002 -0.2094 0.068 Uiso 1 1 calc R . .
C1 C 0.7242(3) 0.2421(9) 0.1136(2) 0.0544(10) Uani 1 1 d . . .
C6 C 0.7610(3) 0.4443(9) 0.1695(2) 0.0620(11) Uani 1 1 d . . .
H6 H 0.7273 0.4976 0.2037 0.074 Uiso 1 1 calc R . .
C16 C 0.5540(3) -0.5191(9) -0.0930(2) 0.0600(11) Uani 1 1 d . . .
H16 H 0.5103 -0.5236 -0.0645 0.072 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I4 0.0664(2) 0.0671(2) 0.0870(3) -0.01189(16) 0.01112(17) -0.01061(15)
S13 0.0650(7) 0.0483(5) 0.0528(6) -0.0035(5) 0.0212(5) -0.0048(5)
O1 0.076(2) 0.082(2) 0.077(2) -0.0219(17) 0.0391(18) -0.0090(17)
N11 0.057(2) 0.0518(19) 0.0474(19) 0.0028(16) 0.0141(15) 0.0038(16)
C14 0.063(3) 0.0382(19) 0.047(2) 0.0072(17) 0.0079(19) 0.0066(17)
C2 0.056(2) 0.0394(19) 0.045(2) 0.0025(17) 0.0119(17) 0.0054(17)
C18 0.075(3) 0.053(2) 0.052(3) -0.005(2) 0.005(2) 0.006(2)
C4 0.063(3) 0.043(2) 0.046(2) 0.0031(18) 0.0071(19) 0.0020(18)
C12 0.056(2) 0.0411(19) 0.042(2) 0.0058(16) 0.0111(17) 0.0043(18)
C17 0.061(3) 0.061(3) 0.060(3) -0.003(2) 0.001(2) -0.003(2)
C3 0.059(3) 0.042(2) 0.049(2) 0.0054(18) 0.0113(19) 0.0097(18)
C15 0.058(2) 0.043(2) 0.042(2) 0.0049(17) 0.0076(18) 0.0061(18)
C5 0.086(3) 0.044(2) 0.047(2) -0.0022(19) 0.014(2) 0.002(2)
C19 0.072(3) 0.050(2) 0.049(2) -0.002(2) 0.017(2) 0.007(2)
C1 0.057(3) 0.054(2) 0.052(2) 0.0050(19) 0.016(2) 0.0045(19)
C6 0.080(3) 0.058(2) 0.054(3) -0.008(2) 0.029(2) 0.002(2)
C16 0.053(2) 0.065(3) 0.061(3) 0.001(2) 0.014(2) -0.003(2)
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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 S13 C12 89.0(2) . . ?
C12 N11 C15 111.3(3) . . ?
C19 C14 C15 121.2(4) . . ?
C19 C14 S13 128.8(4) . . ?
C15 C14 S13 110.1(3) . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 C12 121.1(4) . . ?
C1 C2 C12 120.2(4) . . ?
C19 C18 C17 121.2(4) . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 I4 120.5(3) . . ?
C3 C4 I4 119.3(3) . . ?
N11 C12 C2 122.8(4) . . ?
N11 C12 S13 115.4(3) . . ?
C2 C12 S13 121.8(3) . . ?
C16 C17 C18 121.2(4) . . ?
C4 C3 C2 120.6(4) . . ?
C16 C15 N11 125.7(4) . . ?
C16 C15 C14 120.1(4) . . ?
N11 C15 C14 114.2(3) . . ?
C4 C5 C6 120.4(4) . . ?
C18 C19 C14 117.7(4) . . ?
O1 C1 C6 118.4(4) . . ?
O1 C1 C2 122.1(4) . . ?
C6 C1 C2 119.4(4) . . ?
C5 C6 C1 120.6(4) . . ?
C17 C16 C15 118.7(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I4 C4 2.101(4) . ?
S13 C14 1.734(4) . ?
S13 C12 1.748(4) . ?
O1 C1 1.345(5) . ?
N11 C12 1.300(5) . ?
N11 C15 1.395(5) . ?
C14 C19 1.392(5) . ?
C14 C15 1.397(6) . ?
C2 C3 1.388(6) . ?
C2 C1 1.405(6) . ?
C2 C12 1.464(5) . ?
C18 C19 1.378(6) . ?
C18 C17 1.394(7) . ?
C4 C5 1.366(6) . ?
C4 C3 1.380(5) . ?
C17 C16 1.367(6) . ?
C15 C16 1.391(5) . ?
C5 C6 1.369(6) . ?
C1 C6 1.387(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660047
