#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/95/2239502.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_2239502
loop_
_publ_author_name
'Li, Xueshu'
'Parkin, Sean'
'Lehmler, Hans-Joachim'
_publ_section_title
;
 2,4-Dichloro-1-iodo-6-nitrobenzene
;
_journal_coeditor_code           LH5698
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o607
_journal_paper_doi               10.1107/S1600536814008733
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C6 H2 Cl2 I N O2'
_chemical_formula_moiety         'C6 H2 Cl2 I N O2'
_chemical_formula_sum            'C6 H2 Cl2 I N O2'
_chemical_formula_weight         317.89
_chemical_name_systematic
;
2,4-Dichloro-1-iodo-6-nitrobenzene
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7760(5)
_cell_length_b                   6.8989(4)
_cell_length_c                   14.3518(8)
_cell_measurement_reflns_used    6956
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      67.74
_cell_measurement_theta_min      5.91
_cell_volume                     868.93(9)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics
'XP in SHELXTL (Sheldrick, 2008a)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008a) and CIFFIX (Parkin, 2013)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008a)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9625
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.993
_diffrn_reflns_theta_min         5.910
_exptl_absorpt_coefficient_mu    34.296
_exptl_absorpt_correction_T_max  0.216
_exptl_absorpt_correction_T_min  0.052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008b)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    2.430
_exptl_crystal_description       'rounded block'
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.682
_refine_ls_extinction_coef       0.0021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL2013 (Sheldrick, 2008a)'
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0368
_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)+(0.0668P)²+0.2013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0983
_reflns_number_gt                827
_reflns_number_total             862
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5698sup1.cif
_cod_data_source_block           I
_cod_database_code               2239502
_cod_database_fobs_code          2239502
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelx_estimated_absorpt_t_min   0.095
_shelx_estimated_absorpt_t_max   0.341
_shelxl_version_number           .2013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
I I1 0.10397(4) 0.2500 0.70325(2) 0.0776(3) Uani d 1
Cl Cl1 -0.18714(15) 0.2500 0.54761(10) 0.0783(4) Uani d 1
Cl Cl2 0.16156(18) 0.2500 0.24439(10) 0.0807(4) Uani d 1
N N1 0.4037(5) 0.2500 0.5700(4) 0.0797(14) Uani d 1
O O1 0.4576(4) 0.4066(6) 0.5918(2) 0.0946(9) Uani d 1
C C1 0.1230(7) 0.2500 0.5590(5) 0.0739(13) Uani d 1
C C2 -0.0053(7) 0.2500 0.5003(5) 0.0753(13) Uani d 1
C C3 0.0065(7) 0.2500 0.4060(4) 0.0754(13) Uani d 1
H H3 -0.0828 0.2500 0.3686 0.090 Uiso calc 1
C C4 0.1510(8) 0.2500 0.3637(5) 0.0740(13) Uani d 1
C C5 0.2811(7) 0.2500 0.4179(5) 0.0765(13) Uani d 1
H H5 0.3796 0.2500 0.3904 0.092 Uiso calc 1
C C6 0.2624(7) 0.2500 0.5133(4) 0.0757(13) Uani 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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
O1 N1 O1 . 7_565 124.6(6)
O1 N1 C6 . . 117.7(3)
O1 N1 C6 7_565 . 117.7(3)
C6 C1 C2 . . 114.9(6)
C6 C1 I1 . . 122.9(5)
C2 C1 I1 . . 122.2(5)
C3 C2 C1 . . 122.4(6)
C3 C2 Cl1 . . 117.4(5)
C1 C2 Cl1 . . 120.2(5)
C2 C3 C4 . . 119.9(6)
C2 C3 H3 . . 120.0
C4 C3 H3 . . 120.0
C5 C4 C3 . . 120.2(6)
C5 C4 Cl2 . . 121.1(5)
C3 C4 Cl2 . . 118.7(5)
C6 C5 C4 . . 117.4(6)
C6 C5 H5 . . 121.3
C4 C5 H5 . . 121.3
C5 C6 C1 . . 125.1(6)
C5 C6 N1 . . 116.5(5)
C1 C6 N1 . . 118.4(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 C1 . 2.077(7)
Cl1 C2 . 1.734(7)
Cl2 C4 . 1.715(7)
N1 O1 . 1.220(4)
N1 O1 7_565 1.220(4)
N1 C6 . 1.484(8)
C1 C6 . 1.388(9)
C1 C2 . 1.406(9)
C2 C3 . 1.358(9)
C3 C4 . 1.406(10)
C3 H3 . 0.9500
C4 C5 . 1.381(9)
C5 C6 . 1.379(9)
C5 H5 . 0.9500
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
C3 H3 Cl2 6_556 0.95 2.77 3.718(7) 179
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
C6 C1 C2 C3 . 0.000(2)
I1 C1 C2 C3 . 180.0000(10)
C6 C1 C2 Cl1 . 180.0000(10)
I1 C1 C2 Cl1 . 0.0000(10)
C1 C2 C3 C4 . 0.000(2)
Cl1 C2 C3 C4 . 180.0000(10)
C2 C3 C4 C5 . 0.000(2)
C2 C3 C4 Cl2 . 180.0000(10)
C3 C4 C5 C6 . 0.0000(10)
Cl2 C4 C5 C6 . 180.0000(10)
C4 C5 C6 C1 . 0.000(2)
C4 C5 C6 N1 . 180.0000(10)
C2 C1 C6 C5 . 0.000(2)
I1 C1 C6 C5 . 180.0000(10)
C2 C1 C6 N1 . 180.0000(10)
I1 C1 C6 N1 . 0.000(2)
O1 N1 C6 C5 . 90.0(5)
O1 N1 C6 C5 7_565 -90.0(5)
O1 N1 C6 C1 . -90.0(5)
O1 N1 C6 C1 7_565 90.0(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 43381252
