#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/89/2218996.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_2218996
loop_
_publ_author_name
'Brito, Iván'
'Cárdenas, Alejandro'
'Mundaca, Aldo'
'López-Rodríguez, Matías'
'Reyes, Andrea'
_publ_section_title
;
 2-Iodo-N-(2-nitrophenylsulfanyl)aniline
;
_journal_coeditor_code           FL2204
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1387
_journal_paper_doi               10.1107/S1600536808019491
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C12 H9 I N2 O2 S'
_chemical_formula_moiety         'C12 H9 I N2 O2 S'
_chemical_formula_sum            'C12 H9 I N2 O2 S'
_chemical_formula_weight         372.17
_chemical_melting_point          472
_chemical_name_systematic
;
2-Iodo-N-(2-nitrophenylsulfanyl)aniline
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   28.6221(12)
_cell_length_b                   28.6221(12)
_cell_length_c                   8.4062(17)
_cell_measurement_reflns_used    909
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      1.4
_cell_volume                     5963.9(13)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.96
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ scans, and ω scans with κ  offsets'
_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  0.0588
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11358
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.53
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    2.568
_exptl_absorpt_correction_T_max  0.600
_exptl_absorpt_correction_T_min  0.380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3240
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.038
_refine_diff_density_min         -1.046
_refine_ls_extinction_coef       0.0064(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.212
_refine_ls_R_factor_gt           0.0716
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.087P)²+39.1076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2049
_reflns_number_gt                2801
_reflns_number_total             3251
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2204.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2218996
_cod_database_fobs_code          2218996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
I I1 1.003222(18) 0.07997(2) 0.27240(7) 0.0680(3) Uani d . 1
S S1 0.81458(6) -0.00495(6) 0.12352(17) 0.0458(4) Uani d . 1
N N1 0.8810(2) 0.0367(2) 0.1625(7) 0.0565(13) Uani d . 1
H H1 0.9042 0.0289 0.1244 0.068 Uiso calc R 1
N N2 0.70588(19) -0.0418(2) -0.0484(7) 0.0529(12) Uani d . 1
O O1 0.7146(2) -0.0679(2) 0.0488(7) 0.0679(13) Uani d . 1
O O2 0.6610(2) -0.0547(3) -0.0985(9) 0.0865(19) Uani d . 1
C C1 0.9522(2) 0.1110(2) 0.3204(7) 0.0450(12) Uani d . 1
C C2 0.8998(2) 0.0847(2) 0.2574(6) 0.0427(11) Uani d . 1
C C3 0.8677(3) 0.1073(3) 0.2903(7) 0.0498(13) Uani d . 1
H H3 0.8328 0.0909 0.25 0.06 Uiso calc R 1
C C4 0.8862(3) 0.1532(3) 0.3809(8) 0.0559(15) Uani d . 1
H H4 0.8642 0.1679 0.3997 0.067 Uiso calc R 1
C C5 0.9383(3) 0.1777(3) 0.4448(8) 0.0596(17) Uani d . 1
H H5 0.9507 0.2083 0.5081 0.072 Uiso calc R 1
C C6 0.9706(3) 0.1569(2) 0.4143(7) 0.0518(14) Uani d . 1
H H6 1.0053 0.1733 0.4562 0.062 Uiso calc R 1
C C7 0.80300(19) 0.02629(18) -0.0433(6) 0.0340(9) Uani d . 1
C C8 0.75198(19) 0.00701(19) -0.1113(6) 0.0365(10) Uani d . 1
C C9 0.7438(2) 0.0326(3) -0.2401(7) 0.0482(13) Uani d . 1
H H9 0.7093 0.0191 -0.2816 0.058 Uiso calc R 1
C C10 0.7861(3) 0.0775(3) -0.3060(7) 0.0549(15) Uani d . 1
H H10 0.7809 0.0938 -0.3946 0.066 Uiso calc R 1
C C11 0.8368(3) 0.0982(2) -0.2383(7) 0.0495(13) Uani d . 1
H H11 0.8656 0.1294 -0.2798 0.059 Uiso calc R 1
C C12 0.8450(2) 0.0729(2) -0.1094(6) 0.0391(10) Uani d . 1
H H12 0.8795 0.0875 -0.0663 0.047 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
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
N1 S1 C7 102.9(3)
C2 N1 S1 122.0(5)
C2 N1 H1 119
S1 N1 H1 119
O1 N2 O2 123.7(6)
O1 N2 C8 117.8(5)
O2 N2 C8 118.5(6)
C6 C1 C2 121.3(6)
C6 C1 I1 119.6(5)
C2 C1 I1 119.1(4)
C3 C2 C1 117.1(5)
C3 C2 N1 122.3(5)
C1 C2 N1 120.6(5)
C4 C3 C2 121.6(6)
C4 C3 H3 119.2
C2 C3 H3 119.2
C3 C4 C5 119.9(6)
C3 C4 H4 120.1
C5 C4 H4 120.1
C6 C5 C4 119.8(6)
C6 C5 H5 120.1
C4 C5 H5 120.1
C5 C6 C1 120.3(6)
C5 C6 H6 119.8
C1 C6 H6 119.8
C12 C7 C8 116.5(5)
C12 C7 S1 120.5(4)
C8 C7 S1 122.9(4)
C9 C8 C7 121.8(5)
C9 C8 N2 118.4(5)
C7 C8 N2 119.7(5)
C10 C9 C8 120.5(5)
C10 C9 H9 119.8
C8 C9 H9 119.8
C9 C10 C11 118.8(6)
C9 C10 H10 120.6
C11 C10 H10 120.6
C10 C11 C12 120.8(5)
C10 C11 H11 119.6
C12 C11 H11 119.6
C11 C12 C7 121.5(5)
C11 C12 H12 119.3
C7 C12 H12 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.092(6)
S1 N1 1.696(6)
S1 C7 1.781(5)
N1 C2 1.441(7)
N1 H1 0.86
N2 O1 1.216(8)
N2 O2 1.219(7)
N2 C8 1.458(7)
C1 C6 1.391(9)
C1 C2 1.402(8)
C2 C3 1.392(8)
C3 C4 1.375(9)
C3 H3 0.93
C4 C5 1.400(11)
C4 H4 0.93
C5 C6 1.352(10)
C5 H5 0.93
C6 H6 0.93
C7 C12 1.390(7)
C7 C8 1.399(7)
C8 C9 1.392(8)
C9 C10 1.365(10)
C9 H9 0.93
C10 C11 1.386(10)
C10 H10 0.93
C11 C12 1.387(8)
C11 H11 0.93
C12 H12 0.93
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
_geom_hbond_publ_flag
C10 H10 O1 5_544 0.93 2.55 3.445(10) 161 yes
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
C7 S1 N1 C2 83.9(5)
C6 C1 C2 C3 1.3(8)
I1 C1 C2 C3 -179.0(4)
C6 C1 C2 N1 -179.0(5)
I1 C1 C2 N1 0.8(7)
S1 N1 C2 C3 -16.1(8)
S1 N1 C2 C1 164.2(4)
C1 C2 C3 C4 -0.2(9)
N1 C2 C3 C4 -179.9(6)
C2 C3 C4 C5 -1.2(10)
C3 C4 C5 C6 1.4(10)
C4 C5 C6 C1 -0.3(9)
C2 C1 C6 C5 -1.0(9)
I1 C1 C6 C5 179.2(5)
N1 S1 C7 C12 1.6(5)
N1 S1 C7 C8 -176.3(4)
C12 C7 C8 C9 1.0(7)
S1 C7 C8 C9 178.9(4)
C12 C7 C8 N2 180.0(5)
S1 C7 C8 N2 -2.1(7)
O1 N2 C8 C9 170.0(6)
O2 N2 C8 C9 -8.4(8)
O1 N2 C8 C7 -9.0(8)
O2 N2 C8 C7 172.6(6)
C7 C8 C9 C10 1.0(9)
N2 C8 C9 C10 -178.0(5)
C8 C9 C10 C11 -2.5(9)
C9 C10 C11 C12 2.2(9)
C10 C11 C12 C7 -0.3(9)
C8 C7 C12 C11 -1.3(7)
S1 C7 C12 C11 -179.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24740326
