#------------------------------------------------------------------------------
#$Date: 2024-08-14 04:52:55 +0300 (Wed, 14 Aug 2024) $
#$Revision: 294106 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/25/2312577.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_2312577
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 Br4 I2'
_chemical_formula_moiety         '2(C7 H10 N2), C6 Br4 I2'
_chemical_formula_sum            'C20 H20 Br4 I2 N4'
_chemical_formula_weight         889.832
_chemical_name_systematic
;
4-(Dimethylamino)pyridine--1,2,4,5-tetrabromo-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                102.484(2)
_cell_angle_beta                 108.399(2)
_cell_angle_gamma                113.064(2)
_cell_formula_units_Z            1
_cell_length_a                   8.3361(2)
_cell_length_b                   9.3089(3)
_cell_length_c                   9.8204(2)
_cell_measurement_reflns_used    8887
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      76.1890
_cell_measurement_theta_min      5.1330
_cell_volume                     612.84(4)
_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
;
SHELXT2018 (Sheldrick, 2015)
;
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9397
_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  0.0548
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11315
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.07
_diffrn_reflns_theta_min         5.15
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    27.923
_exptl_absorpt_correction_T_max  0.146
_exptl_absorpt_correction_T_min  0.011
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2023)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    2.411
_exptl_crystal_description       irregular
_exptl_crystal_F_000             412.446
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.8105
_refine_diff_density_min         -1.5901
_refine_ls_goodness_of_fit_ref   1.0305
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0305
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0862P)²+0.8994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                2429
_reflns_number_total             2446
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            vp3039sup1.cif
_cod_data_source_block           2DMAP.DITBB
_cod_database_code               2312577
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 0.66402(4) 0.55739(3) 0.82970(3) 0.02993(15) Uani 1.000000
Br Br1 1.15967(7) 0.73203(6) 1.03222(6) 0.03016(17) Uani 1.000000
Br Br2 1.46760(7) 1.13485(6) 1.18536(6) 0.03136(17) Uani 1.000000
N N1 0.4123(7) 0.2193(6) 0.6942(6) 0.0353(10) Uani 1.000000
N N2 -0.0154(7) -0.2952(6) 0.4640(6) 0.0353(10) Uani 1.000000
C C9 1.0645(7) 0.8856(6) 1.0133(6) 0.0272(9) Uani 1.000000
C C10 1.1981(7) 1.0596(6) 1.0791(6) 0.0275(9) Uani 1.000000
C C3 0.1231(7) -0.1283(6) 0.5382(6) 0.0288(10) Uani 1.000000
C C8 0.8650(7) 0.8220(6) 0.9320(6) 0.0276(10) Uani 1.000000
C C2 0.1625(8) -0.0294(7) 0.6879(6) 0.0326(10) Uani 1.000000
H H2 0.0909(8) -0.0788(7) 0.7395(6) 0.0391(12) Uiso 1.000000
C C4 0.2372(8) -0.0440(7) 0.4711(6) 0.0331(10) Uani 1.000000
H H4 0.2183(8) -0.1031(7) 0.3705(6) 0.0398(12) Uiso 1.000000
C C5 0.3767(8) 0.1251(7) 0.5530(6) 0.0318(10) Uani 1.000000
H H5 0.4529(8) 0.1783(7) 0.5058(6) 0.0381(12) Uiso 1.000000
C C1 0.3051(8) 0.1395(6) 0.7594(6) 0.0313(10) Uani 1.000000
H H1 0.3289(8) 0.2028(6) 0.8605(6) 0.0375(12) Uiso 1.000000
C C6 -0.1347(9) -0.3752(7) 0.5351(7) 0.0389(12) Uani 1.000000
H H6a -0.0505(9) -0.362(6) 0.638(3) 0.0583(18) Uiso 1.000000
H H6b -0.213(6) -0.322(4) 0.546(6) 0.0583(18) Uiso 1.000000
H H6c -0.221(5) -0.4962(15) 0.469(3) 0.0583(18) Uiso 1.000000
C C7 -0.0661(9) -0.3860(7) 0.3027(7) 0.0415(13) Uani 1.000000
H H7a -0.103(7) -0.326(4) 0.2392(13) 0.0623(19) Uiso 1.000000
H H7b 0.046(3) -0.392(6) 0.2968(11) 0.0623(19) Uiso 1.000000
H H7c -0.175(5) -0.501(2) 0.264(2) 0.0623(19) 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
Br 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090 41.43280 2.95570
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
-0.67402 1.33011 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
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)'
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
0 1 0 0.0382
0 -1 0 0.0415
1 -2 2 0.0820
2 1 1 0.0649
-1 -2 0 0.0530
2 -1 1 0.0727
2 -2 1 0.0658
-1 -1 1 0.0654
-1 0 1 0.0913
1 0 -2 0.0970
-1 1 2 0.0578
-1 -1 -2 0.0727
-2 1 0 0.1269
-1 -1 2 0.0611
-1 5 0 0.0586
1 -5 0 0.0502
-2 3 4 0.0503
0 5 -2 0.0530
1 4 0 0.0421
-1 -4 0 0.0434
0 5 -3 0.0580
3 -5 1 0.0660
5 -3 -1 0.0915
5 -3 -3 0.0982
3 0 -4 0.0990
2 -1 -2 0.0982
1 -5 1 0.0541
1 0 -3 0.0900
2 -2 -5 0.0846
1 2 -4 0.0860
0 2 -5 0.0794
0 -5 -1 0.0399
-3 -1 -2 0.0810
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
C1 N1 C5 . . 116.3(5) ?
C6 N2 C3 . . 120.3(5) ?
C7 N2 C3 . . 119.5(5) ?
C7 N2 C6 . . 119.4(5) ?
C10 C9 Br1 . . 118.8(4) ?
C8 C9 Br1 . . 119.3(4) ?
C8 C9 C10 . . 121.9(5) ?
C9 C10 Br2 . . 119.1(4) ?
C8 C10 Br2 2_777 . 120.0(4) ?
C8 C10 C9 2_777 . 121.0(5) ?
C2 C3 N2 . . 121.9(5) ?
C4 C3 N2 . . 122.2(5) ?
C4 C3 C2 . . 115.9(5) ?
C9 C8 I1 . . 121.5(4) ?
C10 C8 I1 2_777 . 121.3(4) ?
C10 C8 C9 2_777 . 117.1(5) ?
H2 C2 C3 . . 120.0(3) ?
C1 C2 C3 . . 120.1(5) ?
C1 C2 H2 . . 120.0(3) ?
H4 C4 C3 . . 120.3(3) ?
C5 C4 C3 . . 119.4(5) ?
C5 C4 H4 . . 120.3(3) ?
C4 C5 N1 . . 124.6(5) ?
H5 C5 N1 . . 117.7(3) ?
H5 C5 C4 . . 117.7(3) ?
C2 C1 N1 . . 123.7(5) ?
H1 C1 N1 . . 118.1(3) ?
H1 C1 C2 . . 118.1(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 . 2.126(5) ?
Br1 C9 . 1.902(5) ?
Br2 C10 . 1.897(5) ?
N1 C5 . 1.338(7) ?
N1 C1 . 1.345(7) ?
N2 C3 . 1.361(7) ?
N2 C6 . 1.454(8) ?
N2 C7 . 1.457(7) ?
C9 C10 . 1.400(7) ?
C9 C8 . 1.393(7) ?
C10 C8 2_777 1.404(7) ?
C3 C2 . 1.411(8) ?
C3 C4 . 1.410(7) ?
C2 H2 . 0.9500 ?
C2 C1 . 1.382(8) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.380(8) ?
C5 H5 . 0.9500 ?
C1 H1 . 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 C9 Br1 . . . . 0.3(4) ?
I1 C8 C9 C10 . . . . 179.1(4) ?
I1 C8 C10 Br2 . . 2_777 2_777 0.6(4) ?
I1 C8 C10 C9 . . 2_777 2_777 -179.1(4) ?
Br1 C9 C10 Br2 . . . . -0.4(4) ?
Br1 C9 C10 C8 . . . 2_777 179.9(4) ?
Br1 C9 C8 C10 . . . 2_777 -179.9(4) ?
Br2 C10 C9 C8 . . . . -179.2(4) ?
Br2 C10 C8 C9 . . 2_777 2_777 179.2(4) ?
N1 C5 C4 C3 . . . . -0.9(7) ?
N1 C1 C2 C3 . . . . 0.4(7) ?
N2 C3 C2 C1 . . . . 179.7(5) ?
N2 C3 C4 C5 . . . . -179.4(5) ?
C9 C10 C8 C9 . . 2_777 2_777 -1.1(4) ?
C9 C8 C10 C9 . . 2_777 2_777 1.1(4) ?

_cod_database_fobs_code 2312577
