#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/98/2239842.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_2239842
loop_
_publ_author_name
'Quinn, Taylor R.'
'Tanski, Joseph M.'
_publ_section_title
;
 Crystal structure of 4-chloro-2-iodoaniline
;
_journal_coeditor_code           JJ2191
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o944
_journal_page_last               o945
_journal_paper_doi               10.1107/S1600536814016869
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C6 H5 Cl I N'
_chemical_formula_moiety         'C6 H5 Cl I N'
_chemical_formula_sum            'C6 H5 Cl I N'
_chemical_formula_weight         253.46
_chemical_name_common            4-Chloro-2-iodoaniline
_chemical_name_systematic
;
4-Chloro-2-iodoaniline
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.1538(4)
_cell_length_b                   11.3685(11)
_cell_length_c                   15.8550(16)
_cell_measurement_reflns_used    5580
_cell_measurement_temperature    125.(2)
_cell_measurement_theta_max      30.3073
_cell_measurement_theta_min      2.2044
_cell_volume                     748.71(13)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL2014 (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL2014 (Sheldrick, 2008), OLEX2 (Dolomanov et al.,
2009) and
Mercury (Macrae et al., 2006)
;
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0657
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11850
_diffrn_reflns_theta_full        30.53
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    4.541
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.961
_refine_diff_density_min         -1.027
_refine_ls_abs_structure_details
;
Flack x determined using 742 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0292
_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)+(0.0156P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0534
_reflns_number_gt                2007
_reflns_number_total             2281
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jj2191sup1.cif
_cod_data_source_block           I
_cod_database_code               2239842
_cod_database_fobs_code          2239842
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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 1.19309(8) 0.92075(3) -0.09588(2) 0.02161(9) Uani d 1
Cl Cl1 1.0100(4) 0.80636(12) 0.24943(10) 0.0322(3) Uani d 1
N N1 0.8012(13) 1.1528(4) -0.0258(3) 0.0236(9) Uani d 1
H H1 0.795(14) 1.124(5) -0.0783(19) 0.028 Uiso d 1
H H2 0.625(10) 1.196(4) -0.017(4) 0.028 Uiso d 1
C C1 0.8463(11) 1.0685(4) 0.0375(3) 0.0187(10) Uani d 1
C C2 1.0139(12) 0.9638(4) 0.0242(3) 0.0167(10) Uani d 1
C C3 1.0695(12) 0.8840(4) 0.0886(3) 0.0190(10) Uani d 1
H H3 1.1867 0.8136 0.0784 0.023 Uiso calc 1
C C4 0.9513(13) 0.9087(5) 0.1680(3) 0.0233(11) Uani d 1
C C5 0.7803(14) 1.0111(5) 0.1839(4) 0.0255(12) Uani d 1
H H5 0.6977 1.0266 0.2387 0.031 Uiso calc 1
C C6 0.7316(12) 1.0906(4) 0.1191(3) 0.0228(11) Uani d 1
H H6 0.6182 1.1615 0.1301 0.027 Uiso calc 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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_3
_geom_angle
C4 Cl1 I1 2_465 86.03(18)
C1 N1 H1 . 115.(4)
C1 N1 H2 . 112.(4)
H1 N1 H2 . 109.(5)
C2 C1 N1 . 122.9(5)
C2 C1 C6 . 117.5(5)
N1 C1 C6 . 119.5(5)
C3 C2 C1 . 122.0(5)
C3 C2 I1 . 117.2(4)
C1 C2 I1 . 120.8(4)
C4 C3 C2 . 118.7(5)
C4 C3 H3 . 120.7
C2 C3 H3 . 120.7
C3 C4 C5 . 121.3(5)
C3 C4 Cl1 . 119.1(4)
C5 C4 Cl1 . 119.6(4)
C6 C5 C4 . 119.2(5)
C6 C5 H5 . 120.4
C4 C5 H5 . 120.4
C5 C6 C1 . 121.3(5)
C5 C6 H6 . 119.4
C1 C6 H6 . 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 C2 . 2.101(5)
Cl1 C4 . 1.755(6)
Cl1 I1 2_465 3.7850(16)
N1 C1 . 1.400(7)
N1 H1 . 0.90(2)
N1 H2 . 0.90(2)
C1 C2 . 1.395(7)
C1 C6 . 1.402(7)
C2 C3 . 1.386(7)
C3 C4 . 1.380(7)
C3 H3 . 0.95
C4 C5 . 1.387(8)
C5 C6 . 1.383(7)
C5 H5 . 0.95
C6 H6 . 0.95
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 I1 3.7850(16) 2_465 y
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
N1 H2 N1 2_475 0.90(2) 2.28(3) 3.142(6) 161(5) y
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
N1 C1 C2 C3 . 176.8(5)
C6 C1 C2 C3 . -0.5(7)
N1 C1 C2 I1 . -3.3(7)
C6 C1 C2 I1 . 179.4(4)
C1 C2 C3 C4 . 0.8(8)
I1 C2 C3 C4 . -179.1(4)
C2 C3 C4 C5 . -0.1(8)
C2 C3 C4 Cl1 . 178.2(4)
I1 Cl1 C4 C3 2_465 -49.3(4)
I1 Cl1 C4 C5 2_465 129.0(4)
C3 C4 C5 C6 . -0.9(8)
Cl1 C4 C5 C6 . -179.2(4)
C4 C5 C6 C1 . 1.2(8)
C2 C1 C6 C5 . -0.5(7)
N1 C1 C6 C5 . -177.9(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 2757615
