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#$Date: 2022-02-04 05:20:17 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272546 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244026.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_2244026
loop_
_publ_author_name
'Luz, Eduardo Q.'
'Santana, Francielli S.'
'Silverio, Gabriel L.'
'Tullio, Suelen C. M. C.'
'Iodice, Bianca'
'Prola, Liziê D. T.'
'Barbosa, Ronilson V.'
'Rampon, Daniel S.'
_publ_section_title
;
 Crystal structures of
 3-halo-2-organochalcogenylbenzo[b]chalcogenophenes
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022000962
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C14 H9 I S2'
_chemical_formula_moiety         'C14 H9 I S2'
_chemical_formula_structural     C14H9IS2
_chemical_formula_sum            'C14 H9 I S2'
_chemical_formula_weight         368.23
_chemical_name_systematic
;
3-Iodo-2-(phenylsulfanyl)benzo[b]thiophene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 97.0520(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4872(3)
_cell_length_b                   9.9629(4)
_cell_length_c                   15.6485(7)
_cell_measurement_reflns_used    9841
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.62
_cell_volume                     1313.18(9)
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and WINGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            56046
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.623
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.729
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.855
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0219
_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)+(0.0218P)²+0.8146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0485
_refine_ls_wR_factor_ref         0.0506
_reflns_number_gt                2585
_reflns_number_total             3001
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jy2015sup1.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2244026
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C2 0.6667(3) 0.8425(2) -0.08322(15) 0.0350(5) Uani d 1 . .
C C3 0.7271(2) 0.9337(2) -0.02410(14) 0.0308(4) Uani d 1 . .
C C4 0.6724(2) 1.0681(2) -0.04289(13) 0.0279(4) Uani d 1 . .
C C5 0.7097(3) 1.1876(2) 0.00262(15) 0.0351(5) Uani d 1 . .
C C6 0.6420(3) 1.3057(2) -0.02866(17) 0.0415(5) Uani d 1 . .
C C7 0.5388(3) 1.3091(2) -0.10526(17) 0.0434(6) Uani d 1 . .
C C8 0.5000(3) 1.1942(2) -0.15099(15) 0.0397(5) Uani d 1 . .
C C9 0.5672(2) 1.0732(2) -0.11926(13) 0.0306(4) Uani d 1 . .
C C11 0.8796(3) 0.6562(2) -0.13223(14) 0.0359(5) Uani d 1 . .
C C12 0.9622(3) 0.5360(2) -0.11839(17) 0.0459(6) Uani d 1 . .
C C13 1.1021(3) 0.5172(3) -0.15346(19) 0.0547(7) Uani d 1 . .
C C14 1.1602(3) 0.6167(3) -0.20217(19) 0.0539(7) Uani d 1 . .
C C15 1.0784(3) 0.7353(3) -0.21568(17) 0.0466(6) Uani d 1 . .
C C16 0.9382(3) 0.7558(2) -0.18094(16) 0.0408(5) Uani d 1 . .
S S1 0.53633(8) 0.91592(6) -0.16492(4) 0.04052(14) Uani d 1 . .
S S10 0.69891(8) 0.66946(6) -0.08560(5) 0.04924(16) Uani d 1 . .
I I1 0.88517(2) 0.88685(2) 0.08375(2) 0.04613(7) Uani d 1 . .
H H5 0.779(3) 1.183(3) 0.0538(17) 0.047(7) Uiso d 1 . .
H H6 0.667(3) 1.387(3) -0.0011(18) 0.048(8) Uiso d 1 . .
H H7 0.502(3) 1.394(3) -0.1290(19) 0.059(9) Uiso d 1 . .
H H8 0.434(3) 1.196(3) -0.2021(17) 0.049(7) Uiso d 1 . .
H H12 0.924(3) 0.471(3) -0.0845(17) 0.049(7) Uiso d 1 . .
H H13 1.162(3) 0.435(3) -0.1465(19) 0.061(8) Uiso d 1 . .
H H14 1.251(4) 0.604(3) -0.229(2) 0.071(10) Uiso d 1 . .
H H15 1.116(3) 0.797(3) -0.2450(17) 0.043(7) Uiso d 1 . .
H H16 0.882(3) 0.829(3) -0.1901(18) 0.053(8) Uiso d 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 C2 S1 . . 111.84(17) ?
C3 C2 S10 . . 129.12(18) ?
S1 C2 S10 . . 119.02(14) ?
C2 C3 C4 . . 113.64(19) ?
C2 C3 I1 . . 123.89(16) ?
C4 C3 I1 . . 122.46(16) ?
C9 C4 C5 . . 118.87(19) ?
C9 C4 C3 . . 111.34(19) ?
C5 C4 C3 . . 129.8(2) ?
C6 C5 C4 . . 119.2(2) ?
C6 C5 H5 . . 122.5(17) ?
C4 C5 H5 . . 118.3(17) ?
C5 C6 C7 . . 121.2(2) ?
C5 C6 H6 . . 121.4(17) ?
C7 C6 H6 . . 117.3(17) ?
C8 C7 C6 . . 120.9(2) ?
C8 C7 H7 . . 119.3(18) ?
C6 C7 H7 . . 119.5(18) ?
C7 C8 C9 . . 118.3(2) ?
C7 C8 H8 . . 121.6(18) ?
C9 C8 H8 . . 120.0(18) ?
C8 C9 C4 . . 121.5(2) ?
C8 C9 S1 . . 126.88(17) ?
C4 C9 S1 . . 111.62(15) ?
C16 C11 C12 . . 119.7(2) ?
C16 C11 S10 . . 123.96(19) ?
C12 C11 S10 . . 116.29(19) ?
C13 C12 C11 . . 119.8(3) ?
C13 C12 H12 . . 120.7(17) ?
C11 C12 H12 . . 119.5(17) ?
C14 C13 C12 . . 120.4(3) ?
C14 C13 H13 . . 117.1(18) ?
C12 C13 H13 . . 122.5(18) ?
C15 C14 C13 . . 119.7(3) ?
C15 C14 H14 . . 118(2) ?
C13 C14 H14 . . 122(2) ?
C14 C15 C16 . . 120.7(3) ?
C14 C15 H15 . . 119.1(18) ?
C16 C15 H15 . . 120.2(18) ?
C11 C16 C15 . . 119.7(2) ?
C11 C16 H16 . . 117.6(19) ?
C15 C16 H16 . . 122.6(19) ?
C9 S1 C2 . . 91.54(11) ?
C2 S10 C11 . . 103.12(11) ?
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
C2 C3 . 1.353(3) ?
C2 S1 . 1.745(2) ?
C2 S10 . 1.746(2) ?
C3 C4 . 1.436(3) ?
C3 I1 . 2.076(2) ?
C4 C9 . 1.402(3) ?
C4 C5 . 1.403(3) ?
C5 C6 . 1.374(3) ?
C5 H5 . 0.93(3) ?
C6 C7 . 1.395(4) ?
C6 H6 . 0.93(3) ?
C7 C8 . 1.369(4) ?
C7 H7 . 0.96(3) ?
C8 C9 . 1.399(3) ?
C8 H8 . 0.92(3) ?
C9 S1 . 1.728(2) ?
C11 C16 . 1.381(3) ?
C11 C12 . 1.391(3) ?
C11 S10 . 1.782(2) ?
C12 C13 . 1.380(4) ?
C12 H12 . 0.92(3) ?
C13 C14 . 1.378(4) ?
C13 H13 . 0.96(3) ?
C14 C15 . 1.374(4) ?
C14 H14 . 0.93(3) ?
C15 C16 . 1.383(4) ?
C15 H15 . 0.85(3) ?
C16 H16 . 0.87(3) ?
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
S1 C2 C3 C4 . . . . -0.9(2) ?
S10 C2 C3 C4 . . . . -179.35(17) ?
S1 C2 C3 I1 . . . . 179.47(11) ?
S10 C2 C3 I1 . . . . 1.0(3) ?
C2 C3 C4 C9 . . . . 0.1(3) ?
I1 C3 C4 C9 . . . . 179.77(14) ?
C2 C3 C4 C5 . . . . -179.4(2) ?
I1 C3 C4 C5 . . . . 0.2(3) ?
C9 C4 C5 C6 . . . . 0.2(3) ?
C3 C4 C5 C6 . . . . 179.7(2) ?
C4 C5 C6 C7 . . . . -0.9(4) ?
C5 C6 C7 C8 . . . . 0.9(4) ?
C6 C7 C8 C9 . . . . -0.3(4) ?
C7 C8 C9 C4 . . . . -0.3(3) ?
C7 C8 C9 S1 . . . . 179.78(19) ?
C5 C4 C9 C8 . . . . 0.4(3) ?
C3 C4 C9 C8 . . . . -179.2(2) ?
C5 C4 C9 S1 . . . . -179.70(16) ?
C3 C4 C9 S1 . . . . 0.7(2) ?
C16 C11 C12 C13 . . . . 0.0(4) ?
S10 C11 C12 C13 . . . . 179.1(2) ?
C11 C12 C13 C14 . . . . -0.1(4) ?
C12 C13 C14 C15 . . . . 0.1(4) ?
C13 C14 C15 C16 . . . . 0.0(4) ?
C12 C11 C16 C15 . . . . 0.1(4) ?
S10 C11 C16 C15 . . . . -178.93(19) ?
C14 C15 C16 C11 . . . . -0.1(4) ?
C8 C9 S1 C2 . . . . 178.9(2) ?
C4 C9 S1 C2 . . . . -1.01(17) ?
C3 C2 S1 C9 . . . . 1.09(17) ?
S10 C2 S1 C9 . . . . 179.73(14) ?
C3 C2 S10 C11 . . . . -83.5(2) ?
S1 C2 S10 C11 . . . . 98.17(15) ?
C16 C11 S10 C2 . . . . -20.5(2) ?
C12 C11 S10 C2 . . . . 160.48(19) ?

_cod_database_fobs_code 2244026
