#------------------------------------------------------------------------------
#$Date: 2024-08-14 04:52:55 +0300 (Wed, 14 Aug 2024) $
#$Revision: 294106 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/25/2312576.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_2312576
loop_
_publ_author_name
'Bosch, Eric'
'Bowling, Nathan P.'
_publ_section_title
;
 Role of secondary interactions in a series of 2:1 halogen-bonded
 cocrystals formed between 4-(dimethylamino)pyridine and ditopic
 halogen-bond donors.
;
_journal_coeditor_code           VP3039
_journal_issue                   9
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S205322962400771X
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          '2C7 H10 N2, C6 Cl4 I2'
_chemical_formula_moiety         '2(C7 H10 N2), C6 Cl4 I2'
_chemical_formula_sum            'C20 H20 Cl4 I2 N4'
_chemical_formula_weight         712.028
_chemical_name_systematic
;
4-(Dimethylamino)pyridine--1,2,4,5-tetrachloro-3,6-diiodobenzene (2/1)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                103.727(3)
_cell_angle_beta                 107.165(3)
_cell_angle_gamma                112.180(4)
_cell_formula_units_Z            1
_cell_length_a                   8.1680(3)
_cell_length_b                   9.1290(4)
_cell_length_c                   9.8118(3)
_cell_measurement_reflns_used    5533
_cell_measurement_temperature    99.9(7)
_cell_measurement_theta_max      76.7430
_cell_measurement_theta_min      5.1670
_cell_volume                     594.91(5)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
olex2.refine (Bourhis et al., 2015)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015)
;
_diffrn_ambient_temperature      99.9(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.9796
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8921
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.78
_diffrn_reflns_theta_min         5.13
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    25.027
_exptl_absorpt_correction_T_max  0.510
_exptl_absorpt_correction_T_min  0.104
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2023)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_description       block
_exptl_crystal_F_000             344.569
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.3301
_refine_diff_density_min         -1.5107
_refine_ls_goodness_of_fit_ref   1.0238
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0238
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0833P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                2413
_reflns_number_total             2500
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            vp3039sup1.cif
_cod_data_source_block           2DMAP.DITCB
_cod_database_code               2312576
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
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_occupancy
I I1 0.66832(3) 0.55170(3) 0.83016(2) 0.02027(14) Uani 1.000000
Cl Cl1 0.55433(14) 0.87164(13) 0.82188(12) 0.0244(2) Uani 1.000000
Cl Cl2 0.84204(14) 1.25822(12) 0.96798(12) 0.0236(2) Uani 1.000000
N N1 0.4176(6) 0.2104(5) 0.6920(5) 0.0256(8) Uani 1.000000
N N2 -0.0264(6) -0.3045(5) 0.4505(5) 0.0265(8) Uani 1.000000
C C10 0.9318(6) 1.1168(5) 0.9868(5) 0.0191(7) Uani 1.000000
C C2 0.3727(6) 0.1184(6) 0.5449(5) 0.0250(8) Uani 1.000000
H H2 0.4439(6) 0.1742(6) 0.4948(5) 0.0299(10) Uiso 1.000000
C C5 0.1183(6) -0.1363(5) 0.5291(5) 0.0206(8) Uani 1.000000
C C9 0.8010(6) 0.9401(5) 0.9196(5) 0.0197(7) Uani 1.000000
C C1 0.2313(6) -0.0503(6) 0.4621(5) 0.0246(8) Uani 1.000000
H H1 0.2100(6) -0.1089(6) 0.3594(5) 0.0295(10) Uiso 1.000000
C C3 0.3125(6) 0.1261(5) 0.7584(5) 0.0240(8) Uani 1.000000
H H3 0.3424(6) 0.1869(5) 0.8631(5) 0.0287(10) Uiso 1.000000
C C8 0.8668(6) 0.8202(5) 0.9319(5) 0.0197(8) Uani 1.000000
C C4 0.1660(6) -0.0410(6) 0.6849(5) 0.0233(8) Uani 1.000000
H H4 0.0967(6) -0.0928(6) 0.7379(5) 0.0280(10) Uiso 1.000000
C C6 -0.1438(7) -0.3878(6) 0.5229(6) 0.0297(9) Uani 1.000000
H H6a -0.0579(8) -0.381(4) 0.621(2) 0.0445(14) Uiso 1.000000
H H6b -0.218(4) -0.330(3) 0.544(4) 0.0445(14) Uiso 1.000000
H H6c -0.234(4) -0.5088(14) 0.453(2) 0.0445(14) Uiso 1.000000
C C7 -0.0832(7) -0.3915(6) 0.2866(5) 0.0287(9) Uani 1.000000
H H7a -0.119(5) -0.325(3) 0.2303(8) 0.0431(13) Uiso 1.000000
H H7b 0.027(2) -0.402(4) 0.2728(6) 0.0431(13) Uiso 1.000000
H H7c -0.195(4) -0.5064(19) 0.2461(12) 0.0431(13) Uiso 1.000000
loop_
_atom_type_symbol
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_dispersion_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870 51.65120 0.21560
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Cl 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940 47.77840 -9.55740
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
0.36843 0.69943 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
H 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236 57.79970 0.00304
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
I 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600 66.87760 4.07120
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
-0.19206 6.94430 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750 0.58260 -11.52900
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 2 0 0.0651
-1 -2 0 0.0710
1 0 -2 0.0500
-1 0 2 0.0500
1 -1 0 0.0080
-1 1 0 0.0243
-1 -1 0 0.0702
1 1 0 0.0631
0 1 -2 0.0503
0 -1 2 0.0464
-2 1 0 0.0420
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
_geom_angle_publ_flag
C3 N1 C2 . . 115.7(4) ?
C6 N2 C5 . . 120.4(4) ?
C7 N2 C5 . . 119.7(4) ?
C7 N2 C6 . . 119.2(4) ?
C9 C10 Cl2 . . 119.0(3) ?
C8 C10 Cl2 2_777 . 119.9(3) ?
C8 C10 C9 2_777 . 121.1(4) ?
H2 C2 N1 . . 117.8(2) ?
C1 C2 N1 . . 124.4(4) ?
C1 C2 H2 . . 117.8(3) ?
C1 C5 N2 . . 122.1(4) ?
C4 C5 N2 . . 121.8(4) ?
C4 C5 C1 . . 116.1(4) ?
C10 C9 Cl1 . . 118.5(3) ?
C8 C9 Cl1 . . 120.4(3) ?
C8 C9 C10 . . 121.1(4) ?
C5 C1 C2 . . 119.9(4) ?
H1 C1 C2 . . 120.1(3) ?
H1 C1 C5 . . 120.1(2) ?
H3 C3 N1 . . 117.8(3) ?
C4 C3 N1 . . 124.3(4) ?
C4 C3 H3 . . 117.8(3) ?
C10 C8 I1 2_777 . 121.0(3) ?
C9 C8 I1 . . 121.2(3) ?
C9 C8 C10 . 2_777 117.8(4) ?
C3 C4 C5 . . 119.5(4) ?
H4 C4 C5 . . 120.3(2) ?
H4 C4 C3 . . 120.3(3) ?
H6a C6 N2 . . 109.5 ?
H6b C6 N2 . . 109.5 ?
H6b C6 H6a . . 109.5 ?
H6c C6 N2 . . 109.5 ?
H6c C6 H6a . . 109.5 ?
H6c C6 H6b . . 109.5 ?
H7a C7 N2 . . 109.5 ?
H7b C7 N2 . . 109.5 ?
H7b C7 H7a . . 109.5 ?
H7c C7 N2 . . 109.5 ?
H7c C7 H7a . . 109.5 ?
H7c C7 H7b . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C8 . 2.125(4) ?
Cl1 C9 . 1.730(4) ?
Cl2 C10 . 1.728(4) ?
N1 C2 . 1.343(6) ?
N1 C3 . 1.350(6) ?
N2 C5 . 1.371(6) ?
N2 C6 . 1.453(6) ?
N2 C7 . 1.451(6) ?
C10 C9 . 1.398(6) ?
C10 C8 2_777 1.402(6) ?
C2 H2 . 0.9500 ?
C2 C1 . 1.370(6) ?
C5 C1 . 1.398(6) ?
C5 C4 . 1.417(6) ?
C9 C8 . 1.405(6) ?
C1 H1 . 0.9500 ?
C3 H3 . 0.9500 ?
C3 C4 . 1.367(6) ?
C4 H4 . 0.9500 ?
C6 H6a . 0.9800 ?
C6 H6b . 0.9800 ?
C6 H6c . 0.9800 ?
C7 H7a . 0.9800 ?
C7 H7b . 0.9800 ?
C7 H7c . 0.9800 ?
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
I1 C8 C10 Cl2 . . 2_777 2_777 -0.2(3) ?
I1 C8 C10 C9 . . 2_777 2_777 -179.9(3) ?
I1 C8 C9 Cl1 . . . . 0.6(3) ?
I1 C8 C9 C10 . . . . 179.9(3) ?
Cl1 C9 C10 Cl2 . . . . -0.6(3) ?
Cl1 C9 C10 C8 . . . 2_777 179.7(3) ?
Cl1 C9 C8 C10 . . . 2_777 -179.7(3) ?
Cl2 C10 C9 C8 . . . . -179.9(3) ?
Cl2 C10 C8 C9 . . 2_777 2_777 179.9(3) ?
N1 C2 C1 C5 . . . . 2.1(5) ?
N1 C3 C4 C5 . . . . 0.5(5) ?
N2 C5 C1 C2 . . . . 179.3(4) ?
N2 C5 C4 C3 . . . . 179.5(4) ?
C10 C9 C8 C10 . . . 2_777 -0.4(4) ?
C10 C8 C9 C10 2_777 . . . -0.4(4) ?
C2 C1 C5 C4 . . . . -2.6(5) ?

_cod_database_fobs_code 2312576
