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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/70/7237085.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_7237085
loop_
_publ_author_name
'Kumar, Vijith'
'Leroy, César'
'Bryce, David L.'
_publ_section_title
;
 Halide ion recognition via chalcogen bonding in the solid state and in
 solution. Directionality and linearity
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              6406
_journal_paper_doi               10.1039/C8CE01365A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C14 H10 N4 Se4, 2(C16 H36 N), 2(I)'
_chemical_formula_sum            'C46 H82 I2 N6 Se4'
_chemical_formula_weight         1288.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-08-08 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.341(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.145(4)
_cell_length_b                   8.651(2)
_cell_length_c                   26.550(8)
_cell_measurement_reflns_used    7389
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      25.11
_cell_measurement_theta_min      2.16
_cell_volume                     2772.4(14)
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            29236
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.543
_exptl_absorpt_coefficient_mu    3.794
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_description       plate
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_refine_diff_density_max         1.000
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         5450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0369P)²+0.4769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0730
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3997
_reflns_number_total             5450
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01365a2.cif
_cod_data_source_block           shelx_CCDC2
_cod_original_cell_volume        2772.5(15)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7237085
_shelx_shelxl_version_number     2018/3
_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   0.463
_shelx_estimated_absorpt_t_max   0.565
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
I1 I 0.39759(2) 0.47613(3) 0.66075(2) 0.04496(9) Uani 1 1 d . .
Se1 Se 0.28652(3) 0.71817(4) 0.56499(2) 0.04409(11) Uani 1 1 d . .
Se2 Se 0.16107(3) 0.25272(4) 0.62389(2) 0.04884(12) Uani 1 1 d . .
N3 N 0.3608(2) 0.0099(3) 0.34600(9) 0.0275(6) Uani 1 1 d . .
C2 C 0.0851(2) 0.4161(3) 0.52778(11) 0.0283(7) Uani 1 1 d . .
C3 C 0.0689(2) 0.5729(3) 0.53868(12) 0.0285(7) Uani 1 1 d . .
C12 C 0.2979(3) 0.1138(4) 0.37934(12) 0.0329(8) Uani 1 1 d . .
H12A H 0.229506 0.059213 0.386299 0.040 Uiso 1 1 calc R U
H12B H 0.343953 0.127690 0.412181 0.040 Uiso 1 1 calc R U
C6 C 0.0151(3) 0.3473(4) 0.48940(11) 0.0295(7) Uani 1 1 d . .
H6 H 0.025356 0.241093 0.482152 0.035 Uiso 1 1 calc R U
C4 C 0.1372(3) 0.6547(4) 0.58124(12) 0.0320(7) Uani 1 1 d . .
H4A H 0.145934 0.585717 0.611176 0.038 Uiso 1 1 calc R U
H4B H 0.096537 0.747799 0.590517 0.038 Uiso 1 1 calc R U
C17 C 0.5439(3) -0.0102(4) 0.30607(13) 0.0358(8) Uani 1 1 d . .
H17A H 0.562451 -0.108059 0.324380 0.043 Uiso 1 1 calc R U
H17B H 0.503243 -0.036327 0.272770 0.043 Uiso 1 1 calc R U
C1 C 0.1782(3) 0.3229(4) 0.55422(12) 0.0357(8) Uani 1 1 d . .
H1A H 0.246762 0.385300 0.555479 0.043 Uiso 1 1 calc R U
H1B H 0.188905 0.230471 0.533306 0.043 Uiso 1 1 calc R U
C20 C 0.2937(3) -0.0193(4) 0.29505(12) 0.0329(7) Uani 1 1 d . .
H20A H 0.286840 0.079767 0.276299 0.039 Uiso 1 1 calc R U
H20B H 0.336296 -0.090863 0.275486 0.039 Uiso 1 1 calc R U
C16 C 0.4696(3) 0.0864(4) 0.33615(12) 0.0326(7) Uani 1 1 d . .
H16A H 0.452305 0.184452 0.317710 0.039 Uiso 1 1 calc R U
H16B H 0.511307 0.112815 0.369187 0.039 Uiso 1 1 calc R U
C13 C 0.2655(3) 0.2726(4) 0.35833(12) 0.0353(8) Uani 1 1 d . .
H13A H 0.332867 0.333316 0.353867 0.042 Uiso 1 1 calc R U
H13B H 0.221333 0.262239 0.324864 0.042 Uiso 1 1 calc R U
C8 C 0.3812(3) -0.1424(4) 0.37372(13) 0.0360(8) Uani 1 1 d . .
H8A H 0.309397 -0.181274 0.382891 0.043 Uiso 1 1 calc R U
H8B H 0.408621 -0.217945 0.350030 0.043 Uiso 1 1 calc R U
C9 C 0.4619(3) -0.1377(4) 0.42103(13) 0.0393(8) Uani 1 1 d . .
H9A H 0.442850 -0.050677 0.442670 0.047 Uiso 1 1 calc R U
H9B H 0.537575 -0.119738 0.411689 0.047 Uiso 1 1 calc R U
C10 C 0.4599(3) -0.2875(4) 0.45054(12) 0.0426(9) Uani 1 1 d . .
H10A H 0.383236 -0.308692 0.457948 0.051 Uiso 1 1 calc R U
H10B H 0.483356 -0.373561 0.429566 0.051 Uiso 1 1 calc R U
C22 C 0.1261(3) -0.1142(4) 0.24281(14) 0.0476(9) Uani 1 1 d . .
H22A H 0.177325 -0.176420 0.224497 0.057 Uiso 1 1 calc R U
H22B H 0.114690 -0.013888 0.225022 0.057 Uiso 1 1 calc R U
C21 C 0.1791(3) -0.0852(4) 0.29615(14) 0.0426(9) Uani 1 1 d . .
H21A H 0.133105 -0.011976 0.313406 0.051 Uiso 1 1 calc R U
H21B H 0.183606 -0.183400 0.315430 0.051 Uiso 1 1 calc R U
C7 C 0.0512(4) 0.1081(5) 0.60659(16) 0.0561(11) Uani 1 1 d . .
C5 C 0.2378(3) 0.8707(5) 0.51842(15) 0.0516(10) Uani 1 1 d . .
N1 N 0.2201(4) 0.9693(4) 0.49042(15) 0.0746(11) Uani 1 1 d . .
C14 C 0.1983(3) 0.3546(4) 0.39477(15) 0.0484(10) Uani 1 1 d . .
H14A H 0.131298 0.292407 0.398562 0.058 Uiso 1 1 calc R U
H14B H 0.242571 0.359377 0.428357 0.058 Uiso 1 1 calc R U
N2 N -0.0127(4) 0.0106(4) 0.60131(18) 0.0840(13) Uani 1 1 d . .
C19 C 0.7153(3) -0.0106(4) 0.26176(16) 0.0556(11) Uani 1 1 d . .
H19A H 0.675570 -0.007453 0.227577 0.083 Uiso 1 1 calc R U
H19B H 0.726227 -0.118394 0.272516 0.083 Uiso 1 1 calc R U
H19C H 0.787455 0.039981 0.261632 0.083 Uiso 1 1 calc R U
C18 C 0.6487(3) 0.0724(4) 0.29792(16) 0.0544(11) Uani 1 1 d . .
H18A H 0.694455 0.084300 0.330926 0.065 Uiso 1 1 calc R U
H18B H 0.630114 0.177152 0.284562 0.065 Uiso 1 1 calc R U
C11 C 0.5356(3) -0.2809(4) 0.49980(14) 0.0519(10) Uani 1 1 d . .
H11A H 0.611495 -0.259414 0.492617 0.078 Uiso 1 1 calc R U
H11B H 0.533479 -0.380256 0.517394 0.078 Uiso 1 1 calc R U
H11C H 0.510647 -0.198686 0.521277 0.078 Uiso 1 1 calc R U
C15 C 0.1631(3) 0.5150(4) 0.37928(17) 0.0588(11) Uani 1 1 d . .
H15A H 0.110012 0.510568 0.348725 0.088 Uiso 1 1 calc R U
H15B H 0.228095 0.575127 0.372256 0.088 Uiso 1 1 calc R U
H15C H 0.128273 0.564309 0.406723 0.088 Uiso 1 1 calc R U
C23 C 0.0160(3) -0.1976(5) 0.24095(19) 0.0761(14) Uani 1 1 d . .
H23A H -0.015800 -0.209269 0.205595 0.114 Uiso 1 1 calc R U
H23B H -0.034779 -0.137524 0.259520 0.114 Uiso 1 1 calc R U
H23C H 0.027374 -0.299839 0.256531 0.114 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 0.0033 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'
Se Se -0.0929 2.2259 '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
C5 Se1 C4 96.29(16) .
C7 Se2 C1 97.05(16) .
C8 N3 C20 109.3(2) .
C8 N3 C12 107.2(2) .
C20 N3 C12 111.1(2) .
C8 N3 C16 111.2(2) .
C20 N3 C16 108.0(2) .
C12 N3 C16 110.0(2) .
C6 C2 C3 118.5(3) .
C6 C2 C1 118.9(3) .
C3 C2 C1 122.6(3) .
C6 C3 C2 118.9(3) 3_566
C6 C3 C4 119.0(3) 3_566
C2 C3 C4 122.1(3) .
C13 C12 N3 116.5(2) .
C3 C6 C2 122.6(3) 3_566
C3 C4 Se1 114.1(2) .
C18 C17 C16 112.2(3) .
C2 C1 Se2 116.8(2) .
C21 C20 N3 116.8(3) .
C17 C16 N3 115.3(3) .
C14 C13 C12 109.0(3) .
C9 C8 N3 116.0(3) .
C8 C9 C10 111.2(3) .
C11 C10 C9 111.8(3) .
C21 C22 C23 113.1(3) .
C20 C21 C22 110.1(3) .
N2 C7 Se2 171.8(4) .
N1 C5 Se1 172.3(4) .
C15 C14 C13 114.7(3) .
C17 C18 C19 113.0(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 C5 1.860(4) .
Se1 C4 1.988(3) .
Se2 C7 1.850(5) .
Se2 C1 1.979(3) .
N3 C8 1.516(4) .
N3 C20 1.521(4) .
N3 C12 1.525(4) .
N3 C16 1.526(4) .
C2 C6 1.387(4) .
C2 C3 1.405(4) .
C2 C1 1.499(4) .
C3 C6 1.380(4) 3_566
C3 C4 1.503(4) .
C12 C13 1.519(4) .
C17 C18 1.496(5) .
C17 C16 1.520(4) .
C20 C21 1.507(5) .
C13 C14 1.510(5) .
C8 C9 1.506(4) .
C9 C10 1.516(4) .
C10 C11 1.514(5) .
C22 C21 1.510(5) .
C22 C23 1.516(5) .
C7 N2 1.145(5) .
C5 N1 1.136(5) .
C14 C15 1.496(5) .
C19 C18 1.505(5) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339917
