#------------------------------------------------------------------------------
#$Date: 2020-08-01 08:04:11 +0300 (Sat, 01 Aug 2020) $
#$Revision: 254731 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/35/2243519.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_2243519
loop_
_publ_author_name
'Medjroubi, Mohamed Larbi'
'Boudjada, Ali'
'Hamdouni, Noudjoud'
'Brihi, Ouarda'
'Jeannin, Olivier'
'Meinnel, Jean'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 2,6-diiodo-4-nitrotoluene and 2,4,6-tribromotoluene
;
_journal_coeditor_code           DJ2011
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1391
_journal_page_last               1397
_journal_paper_doi               10.1107/S2056989020010270
_journal_volume                  76
_journal_year                    2020
_chemical_compound_source        'see text'
_chemical_formula_iupac          'C7 H5 I2 N O2'
_chemical_formula_moiety         'C7 H5 I2 N O2'
_chemical_formula_sum            'C7 H5 I2 N O2'
_chemical_formula_weight         388.92
_chemical_name_systematic
;
2,6-Diiodo-4-nitrotoluene
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 96.5880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.3815(2)
_cell_length_b                   15.3348(6)
_cell_length_c                   14.5894(6)
_cell_measurement_reflns_used    3615
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.81
_cell_volume                     973.78(7)
_computing_cell_refinement
;
SAINT (Bruker, 2006)
;
_computing_data_collection
;
APEX2 (Bruker, 2006)
;
_computing_data_reduction
;
SAINT (Bruker, 2006)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2020)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2004 (Burla et al.,  2005)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4104
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.542
_diffrn_reflns_theta_min         2.656
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.420
_exptl_absorpt_correction_T_max  0.680
_exptl_absorpt_correction_T_min  0.382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.550
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0236
_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)+(0.0064P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0432
_refine_ls_wR_factor_ref         0.0457
_reflns_number_gt                1850
_reflns_number_total             2244
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dj2011sup1.cif
_cod_data_source_block           DINT
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243519
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_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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
I I2 0.49927(5) 0.16308(2) 0.43507(2) 0.02865(8) Uani d . 1 1 . .
I I1 0.61809(6) -0.09049(2) 0.11508(2) 0.03239(8) Uani d . 1 1 . .
O O2 1.0610(7) 0.31383(17) 0.16120(19) 0.0439(7) Uani d . 1 1 . .
O O1 1.2265(6) 0.21412(17) 0.07502(18) 0.0383(6) Uani d . 1 1 . .
N N1 1.0741(6) 0.2380(2) 0.1357(2) 0.0270(7) Uani d . 1 1 . .
C C4 0.9021(7) 0.1719(2) 0.1809(2) 0.0213(7) Uani d . 1 1 . .
C C5 0.7967(7) 0.1926(2) 0.2637(2) 0.0226(7) Uani d . 1 1 . .
C C7 0.4089(8) -0.0220(2) 0.3155(3) 0.0311(8) Uani d . 1 1 . .
C C3 0.8521(7) 0.0917(2) 0.1389(2) 0.0248(8) Uani d . 1 1 . .
C C6 0.6400(7) 0.1288(2) 0.3069(2) 0.0223(7) Uani d . 1 1 . .
C C1 0.5769(7) 0.0462(2) 0.2676(2) 0.0238(8) Uani d . 1 1 . .
C C2 0.6870(7) 0.0302(2) 0.1830(2) 0.0243(8) Uani d . 1 1 . .
H H5 0.830322 0.248772 0.290300 0.027 Uiso calc R 1 1 U .
H H3 0.927896 0.078917 0.081954 0.030 Uiso calc R 1 1 U .
H H7A 0.556153 -0.056139 0.356537 0.047 Uiso calc R 1 1 U .
H H7B 0.298926 -0.060732 0.269445 0.047 Uiso calc R 1 1 U .
H H7C 0.261494 0.006076 0.351681 0.047 Uiso calc R 1 1 U .
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'
I I -0.4742 1.8119 ' 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'
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
O2 N1 O1 . . 123.5(3) ?
O2 N1 C4 . . 118.4(3) ?
O1 N1 C4 . . 118.0(3) ?
C5 C4 C3 . . 122.8(3) ?
C5 C4 N1 . . 118.5(3) ?
C3 C4 N1 . . 118.7(3) ?
C4 C5 C6 . . 118.0(3) ?
C4 C5 H5 . . 121.0 ?
C6 C5 H5 . . 121.0 ?
C1 C7 H7A . . 109.5 ?
C1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C4 C3 C2 . . 117.6(3) ?
C4 C3 H3 . . 121.2 ?
C2 C3 H3 . . 121.2 ?
C5 C6 C1 . . 122.3(3) ?
C5 C6 I2 . . 116.1(2) ?
C1 C6 I2 . . 121.7(3) ?
C2 C1 C6 . . 116.5(3) ?
C2 C1 C7 . . 121.8(3) ?
C6 C1 C7 . . 121.6(3) ?
C3 C2 C1 . . 122.7(3) ?
C3 C2 I1 . . 115.7(3) ?
C1 C2 I1 . . 121.6(3) ?
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
I2 C6 . 2.101(3) ?
I1 C2 . 2.105(3) ?
O2 N1 . 1.224(4) ?
O1 N1 . 1.224(4) ?
N1 C4 . 1.464(4) ?
C4 C5 . 1.378(5) ?
C4 C3 . 1.381(5) ?
C5 C6 . 1.388(5) ?
C5 H5 . 0.9500 ?
C7 C1 . 1.497(5) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C3 C2 . 1.389(5) ?
C3 H3 . 0.9500 ?
C6 C1 . 1.404(5) ?
C1 C2 . 1.398(5) ?
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
O2 N1 C4 C5 . . . . -15.8(4) ?
O1 N1 C4 C5 . . . . 163.4(3) ?
O2 N1 C4 C3 . . . . 164.2(3) ?
O1 N1 C4 C3 . . . . -16.7(4) ?
C3 C4 C5 C6 . . . . 1.5(5) ?
N1 C4 C5 C6 . . . . -178.6(3) ?
C5 C4 C3 C2 . . . . 0.3(5) ?
N1 C4 C3 C2 . . . . -179.7(3) ?
C4 C5 C6 C1 . . . . -2.4(5) ?
C4 C5 C6 I2 . . . . 177.9(2) ?
C5 C6 C1 C2 . . . . 1.5(5) ?
I2 C6 C1 C2 . . . . -178.8(2) ?
C5 C6 C1 C7 . . . . 179.7(3) ?
I2 C6 C1 C7 . . . . -0.6(4) ?
C4 C3 C2 C1 . . . . -1.2(5) ?
C4 C3 C2 I1 . . . . 179.8(2) ?
C6 C1 C2 C3 . . . . 0.3(5) ?
C7 C1 C2 C3 . . . . -177.8(3) ?
C6 C1 C2 I1 . . . . 179.2(2) ?
C7 C1 C2 I1 . . . . 1.1(4) ?

_cod_database_fobs_code 2243519
