#------------------------------------------------------------------------------
#$Date: 2025-08-22 11:56:18 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301860 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/81/7128176.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7128176
loop_
_publ_author_name
'Poynder, Tiffany B.'
'Chamorro Orué, Analia I'
'Tania, ?'
'Sharp-Bucknall, Lachlan'
'Flynn, Matthew T.'
'Wilson, David J. D.'
'Athukorala Arachchige, Kasun S.'
'Clegg, Jack K.'
'Dutton, Jason L.'
_publ_section_title
;
 On the activation of PhICl₂ with pyridine.
;
_journal_issue                   40
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4970
_journal_page_last               4973
_journal_paper_doi               10.1039/d1cc01567b
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C6 H5 Cl2 I'
_chemical_formula_sum            'C6 H5 Cl2 I'
_chemical_formula_weight         274.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-02-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-03-18 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.8700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0910(2)
_cell_length_b                   5.35790(10)
_cell_length_c                   12.42400(10)
_cell_measurement_reflns_used    62344
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      55.6770
_cell_measurement_theta_min      3.2690
_cell_volume                     787.65(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     58.00  88.00   0.50   35.00    --   60.46  57.00  30.00   60
  2  ω     38.00 125.00   0.50   35.00    --   60.46  77.00   0.00  174
  3  ω     49.00 136.00   0.50   35.00    --   60.46  34.00 -93.00  174
  4  ω     41.00 130.00   0.50   35.00    --   60.46 178.00 150.00  178
  5  ω     50.00 136.00   0.50   35.00    --   60.46  37.00 150.00  172
  6  ω    -11.00  76.00   0.50    6.00    --    0.00  34.00 -93.00  174
  7  ω     -1.00  29.00   0.50   35.00    --   60.46 -57.00 -30.00   60
  8  ω    -10.00  44.00   0.50   35.00    --   60.46 -57.00  30.00  108
  9  ω     -4.00  83.00   0.50   35.00    --   60.46 -77.00 -60.00  174
 10  ω    -10.00  44.00   0.50   35.00    --   60.46 -57.00-180.00  108
 11  ω    -15.00  21.00   0.50   35.00    --   60.46 -37.00-180.00   72
 12  ω    -15.00  15.00   0.50   35.00    --   60.46 -37.00 -60.00   60
 13  ω    -10.00  44.00   0.50   35.00    --   60.46 -57.00   0.00  108
 14  ω    -10.00  44.00   0.50   35.00    --   60.46 -57.00  60.00  108
 15  ω    -11.00  20.00   0.50   35.00    --   60.46 -37.00 150.00   62
 16  ω    -15.00  18.00   0.50   35.00    --   60.46 -34.00 108.00   66
 17  ω    -15.00  21.00   0.50   35.00    --   60.46 -37.00  60.00   72
 18  ω    -15.00  11.00   0.50   35.00    --   60.46 -37.00  90.00   52
 19  ω    -23.00  33.00   0.50    6.00    --    0.00 -99.00 120.00  112
 20  ω    -40.00  46.00   0.50   35.00    --  -30.25  34.00 -93.00  172
 21  ω    -76.00  11.00   0.50    6.00    --    0.00 -34.00 108.00  174
 22  ω   -105.00 -19.00   0.50   35.00    --  -30.25 -34.00 108.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0092283000
_diffrn_orient_matrix_UB_12      -0.0441060000
_diffrn_orient_matrix_UB_13      0.0380165000
_diffrn_orient_matrix_UB_21      -0.0457843000
_diffrn_orient_matrix_UB_22      -0.0060902000
_diffrn_orient_matrix_UB_23      -0.0200292000
_diffrn_orient_matrix_UB_31      0.0072406000
_diffrn_orient_matrix_UB_32      -0.0944438000
_diffrn_orient_matrix_UB_33      -0.0164750000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ag K\a'
_diffrn_radiation_wavelength     0.56087
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            112634
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         47.557
_diffrn_reflns_theta_min         2.644
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Ag) X-ray Source'
_exptl_absorpt_coefficient_mu    2.440
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.152
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.318
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_size_rad          0.400
_refine_diff_density_max         2.011
_refine_diff_density_min         -0.874
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         15024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0162
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0180P)²+0.0412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0392
_refine_ls_wR_factor_ref         0.0402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13060
_reflns_number_total             15024
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc01567b2.cif
_cod_data_source_block           PhICl2_IAM
_cod_depositor_comments
'Adding full bibliography for 7128176--7128179.cif.'
_cod_database_code               7128176
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C6 H5 I Cl2'
_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_max   0.910
_shelx_estimated_absorpt_t_min   0.714
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     53.05
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.24873(2) 0.32391(2) 0.39958(2) 0.00975(1) Uani 1 1 d . . . . .
Cl2 Cl 0.37742(2) -0.01936(2) 0.36412(2) 0.01370(1) Uani 1 1 d . . . . .
Cl1 Cl 0.12355(2) 0.65687(2) 0.44604(2) 0.01546(2) Uani 1 1 d . . . . .
C2 C 0.40528(4) 0.51282(7) 0.60308(3) 0.01244(5) Uani 1 1 d . . . . .
H2 H 0.421058 0.638745 0.554548 0.015 Uiso 1 1 calc R U . . .
C1 C 0.33061(3) 0.31978(6) 0.56571(3) 0.01021(4) Uani 1 1 d . . . . .
C3 C 0.45626(4) 0.51502(8) 0.71450(3) 0.01380(5) Uani 1 1 d . . . . .
H3 H 0.507742 0.644432 0.742925 0.017 Uiso 1 1 calc R U . . .
C4 C 0.43215(4) 0.32872(8) 0.78425(3) 0.01345(5) Uani 1 1 d . . . . .
H4 H 0.467093 0.332401 0.860068 0.016 Uiso 1 1 calc R U . . .
C5 C 0.35718(4) 0.13671(9) 0.74393(3) 0.01415(5) Uani 1 1 d . . . . .
H5 H 0.341672 0.009956 0.792218 0.017 Uiso 1 1 calc R U . . .
C6 C 0.30493(4) 0.13026(8) 0.63296(3) 0.01277(5) Uani 1 1 d . . . . .
H6 H 0.253558 0.000850 0.604287 0.015 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0013 0.0009 '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'
Cl Cl 0.1009 0.0992 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.8561 1.1928 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0500
0 0 1 0.0550
0 1 1 0.4827
0 -1 -1 0.4113
1 0 1 0.0737
-1 0 -1 0.0737
-1 0 1 0.0268
1 0 -1 0.0268
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 I1 Cl2 176.701(4) . . ?
C1 I1 Cl2 88.900(10) . . ?
C1 I1 Cl1 88.035(10) . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.54(4) . . ?
C3 C2 H2 121.2 . . ?
C2 C1 I1 117.64(3) . . ?
C2 C1 C6 123.60(4) . . ?
C6 C1 I1 118.72(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.37(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.63(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.17(4) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 117.69(4) . . ?
C1 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Cl2 2.50592(11) . ?
I1 Cl1 2.48319(12) . ?
I1 C1 2.0977(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.3885(5) . ?
C2 C3 1.3947(6) . ?
C1 C6 1.3901(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.3915(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.3943(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.3938(6) . ?
C6 H6 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C6 C5 -177.62(3) . . . . ?
C2 C1 C6 C5 0.24(6) . . . . ?
C2 C3 C4 C5 0.27(7) . . . . ?
C1 C2 C3 C4 0.07(6) . . . . ?
C3 C2 C1 I1 177.55(3) . . . . ?
C3 C2 C1 C6 -0.33(6) . . . . ?
C3 C4 C5 C6 -0.37(7) . . . . ?
C4 C5 C6 C1 0.11(7) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 288571
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0005 -0.0001 -0.9994 -0.0380 0.0200 0.0165
-0.0005 0.0001 0.9994 0.0380 -0.0200 -0.0165
0.0078 1.0002 0.9994 -0.0062 -0.0265 -0.1109
-0.0078 -1.0002 -0.9994 0.0062 0.0265 0.1109
1.0131 0.0001 0.9861 0.0281 -0.0661 -0.0089
-1.0131 -0.0001 -0.9861 -0.0281 0.0661 0.0089
-0.9909 -0.0005 1.0094 0.0475 0.0252 -0.0238
0.9909 0.0005 -1.0094 -0.0475 -0.0252 0.0238
