#------------------------------------------------------------------------------
#$Date: 2023-10-06 03:02:36 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286724 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/72/7247289.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_7247289
loop_
_publ_author_name
'Korobeynikov, Nikita A.'
'Usoltsev, Andrey N.'
'Sokolov, Maxim N.'
'Novikov, Alexander S.'
'Sukhikh, Taisiya S.'
'Adonin, Sergey A.'
_publ_section_title
;
 Halogen bonding in chloroiodates(iii)
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              5233
_journal_page_last               5237
_journal_paper_doi               10.1039/D3CE00400G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'Cl4 I, C8 H12 N'
_chemical_formula_sum            'C8 H12 Cl4 I N'
_chemical_formula_weight         390.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-04-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-19 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.6000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4476(6)
_cell_length_b                   9.9715(4)
_cell_length_c                   7.8504(3)
_cell_measurement_reflns_used    9025
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.00
_cell_measurement_theta_min      2.37
_cell_volume                     1332.91(9)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13777
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.372
_diffrn_reflns_theta_min         2.367
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    3.169
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0525 before and 0.0448 after correction.
The Ratio of minimum to maximum transmission is 0.9091.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.948
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0166
_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)+(0.0121P)²+0.7387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0351
_refine_ls_wR_factor_ref         0.0365
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2021
_reflns_number_total             2315
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00400g2.cif
_cod_data_source_block           nk704_a
_cod_depositor_comments
'Adding full bibliography for 7247286--7247294.cif.'
_cod_database_code               7247289
_shelx_shelxl_version_number     2017/1
_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   0.648
_shelx_estimated_absorpt_t_min   0.648
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Cl1 Cl 0.39466(2) 0.79149(4) 0.55384(5) 0.03039(8) Uani 1 1 d . . . . .
I1 I 0.250000 0.750000 0.500000 0.01887(4) Uani 1 2 d S . P . .
Cl2 Cl 0.23727(2) 0.94528(4) 0.69174(5) 0.02965(8) Uani 1 1 d . . . . .
N1 N 0.500000 0.77299(16) 0.250000 0.0235(3) Uani 1 2 d S T P . .
C1 C 0.500000 0.9204(2) 0.250000 0.0381(5) Uani 1 2 d S T P . .
H1A H 0.462378 0.953206 0.316573 0.057 Uiso 0.5 1 calc R U P . .
H1B H 0.484947 0.953206 0.129626 0.057 Uiso 0.5 1 calc R U P . .
H1C H 0.552675 0.953206 0.303800 0.057 Uiso 0.5 1 calc R U P . .
C2 C 0.37208(11) 0.7838(2) 0.0387(3) 0.0394(4) Uani 1 1 d . . . . .
H2A H 0.3315(15) 0.725(2) -0.019(3) 0.059 Uiso 1 1 d . U . . .
H2B H 0.3513(13) 0.839(2) 0.108(3) 0.059 Uiso 1 1 d . U . . .
H2C H 0.3880(13) 0.836(2) -0.050(3) 0.059 Uiso 1 1 d . U . . .
C3 C 0.43861(8) 0.70595(15) 0.14747(18) 0.0246(3) Uani 1 1 d . . . . .
C4 C 0.43890(8) 0.56842(15) 0.14691(19) 0.0272(3) Uani 1 1 d . . . . .
H4 H 0.396721 0.521003 0.075006 0.033 Uiso 1 1 calc R U . . .
C5 C 0.500000 0.4985(2) 0.250000 0.0285(4) Uani 1 2 d S T P . .
H5 H 0.500001 0.403266 0.249999 0.034 Uiso 1 2 calc R U P . .
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'
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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 I1 Cl1 180.0 . 7_566 ?
Cl2 I1 Cl1 90.669(12) . 7_566 ?
Cl2 I1 Cl1 90.668(12) 7_566 . ?
Cl2 I1 Cl1 89.331(12) . . ?
Cl2 I1 Cl1 89.333(12) 7_566 7_566 ?
Cl2 I1 Cl2 180.0 . 7_566 ?
C3 N1 C1 119.30(8) 2_655 . ?
C3 N1 C1 119.30(8) . . ?
C3 N1 C3 121.39(17) 2_655 . ?
N1 C1 H1A 109.470(7) . 2_655 ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.471(2) . 2_655 ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.470(17) . 2_655 ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1A 141.1 . 2_655 ?
H1A C1 H1B 56.3 . 2_655 ?
H1A C1 H1B 109.5 2_655 2_655 ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 56.3 . 2_655 ?
H1A C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 2_655 2_655 ?
H1B C1 H1A 56.3 . 2_655 ?
H1B C1 H1B 141.1 . 2_655 ?
H1B C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 2_655 2_655 ?
H1B C1 H1C 56.3 . 2_655 ?
H1C C1 H1A 56.3 . 2_655 ?
H1C C1 H1B 56.2 . 2_655 ?
H1C C1 H1C 141.1 . 2_655 ?
H2A C2 H2B 108(2) . . ?
H2A C2 H2C 107(2) . . ?
H2B C2 H2C 109.2(19) . . ?
C3 C2 H2A 110.6(14) . . ?
C3 C2 H2B 109.5(14) . . ?
C3 C2 H2C 112.6(13) . . ?
N1 C3 C2 119.50(15) . . ?
N1 C3 C4 119.23(13) . . ?
C4 C3 C2 121.26(14) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.43(14) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C4 119.28(19) 2_655 . ?
C4 C5 H5 120.4 . . ?
C4 C5 H5 120.4 2_655 . ?
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
Cl1 I1 2.5010(4) . ?
I1 Cl2 2.5005(3) . ?
I1 Cl2 2.5006(3) 7_566 ?
N1 C1 1.470(3) . ?
N1 C3 1.3659(16) 2_655 ?
N1 C3 1.3659(16) . ?
C1 H1A 0.9800 . ?
C1 H1A 0.9800 2_655 ?
C1 H1B 0.9800 . ?
C1 H1B 0.9800 2_655 ?
C1 H1C 0.9800 2_655 ?
C1 H1C 0.9800 . ?
C2 H2A 0.96(2) . ?
C2 H2B 0.91(2) . ?
C2 H2C 0.96(2) . ?
C2 C3 1.499(2) . ?
C3 C4 1.371(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3787(17) . ?
C5 H5 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
N1 C3 C4 C5 0.69(19) . . . . ?
C1 N1 C3 C2 -0.70(15) . . . . ?
C1 N1 C3 C4 179.65(9) . . . . ?
C2 C3 C4 C5 -178.95(13) . . . . ?
C3 N1 C3 C2 179.30(15) 2_655 . . . ?
C3 N1 C3 C4 -0.35(9) 2_655 . . . ?
C3 C4 C5 C4 -0.35(10) . . . 2_655 ?
