#------------------------------------------------------------------------------
#$Date: 2025-05-03 21:18:00 +0200 (Sat 03 de May de 2025) $
#$Revision: 299510 $
#$URL: svn://www.crystallography.net/cod/cif/2/31/27/2312781.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_2312781
loop_
_publ_author_name
'Shapiro, Nicole M.'
'Govero, Mark D.'
'Bosch, Eric'
'Unruh, Daniel K.'
'Groeneman, Ryan H.'
_publ_section_title
;
 Mixed cocrystal approach influences the yield for a [2+2] cycloaddition
 reaction within a halogen-bonded organic solid.
;
_journal_coeditor_code           JX3092
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              193
_journal_page_last               197
_journal_paper_doi               10.1107/S2053229625001913
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C12 H10 N2, 0.75C6 Cl4 I2, 0.25C6 Cl5 I1'
_chemical_formula_moiety         'C12 H10 N2, 0.75(C6 Cl4 I2), 0.25(C6 Cl5 I1)'
_chemical_formula_sum            'C18 H10 Cl4.22 I1.78 N2'
_chemical_formula_weight         629.76
_chemical_name_systematic
;
trans-1,2-Bis(pyridin-4-yl)ethylene
1,4-diiodoperchlorobenzene--iodoperchlorobenzene(0.75/0.25)
;
_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_hydrogens   geom
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                110.4810(10)
_cell_angle_beta                 92.7290(10)
_cell_angle_gamma                94.387(2)
_cell_formula_units_Z            1
_cell_length_a                   4.0273(2)
_cell_length_b                   10.8796(5)
_cell_length_c                   12.3274(5)
_cell_measurement_reflns_used    6939
_cell_measurement_temperature    210
_cell_measurement_theta_max      28.239
_cell_measurement_theta_min      3.113
_cell_volume                     502.90(4)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX6 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      210
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker D8 VENTURE DUO with a Photon III detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18122
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.375
_diffrn_reflns_theta_min         2.008
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    3.355
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    2.079
_exptl_crystal_description       irregular
_exptl_crystal_F_000             298
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.566
_refine_ls_extinction_coef       0.0082(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2019 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2524
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0226
_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)+0.4137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0422
_refine_ls_wR_factor_ref         0.0430
_reflns_number_gt                2425
_reflns_number_total             2524
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jx3092sup1.cif
_cod_data_source_block           C6I2CL4_C6ICl5_BPE_290and210_210
_cod_depositor_comments
'Adding full bibliography for 2312780--2312781.cif.'
_cod_database_code               2312781
_cod_database_fobs_code          2312781
_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   0.543
_shelx_estimated_absorpt_t_max   0.799
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.22857(16) 0.98625(6) 0.72799(5) 0.03525(17) Uani d 1 . .
Cl Cl2 0.40215(17) 0.73240(6) 0.53997(5) 0.03816(18) Uani d 1 . .
N N1 0.8832(6) 0.45561(19) 0.14247(18) 0.0354(5) Uani d 1 . .
C C1 0.3783(5) 0.9951(2) 0.60147(17) 0.0248(4) Uani d 1 . .
C C2 0.4593(5) 0.8800(2) 0.51649(18) 0.0254(4) Uani d 1 . .
C C3 0.5823(5) 0.8830(2) 0.41308(17) 0.0230(4) Uani d 1 . .
C C4 1.0429(7) 0.4086(2) 0.2151(2) 0.0384(6) Uani d 1 . .
H H4 1.111263 0.466832 0.290799 0.046 Uiso calc 1 . .
C C5 1.1123(6) 0.2789(2) 0.1846(2) 0.0333(5) Uani d 1 . .
H H5 1.229782 0.251427 0.238325 0.040 Uiso calc 1 . .
C C6 1.0082(6) 0.1892(2) 0.07423(19) 0.0264(5) Uani d 1 . .
C C7 0.8431(6) 0.2377(2) -0.0018(2) 0.0306(5) Uani d 1 . .
H H7 0.769401 0.181487 -0.077718 0.037 Uiso calc 1 . .
C C8 0.7887(6) 0.3704(2) 0.0362(2) 0.0346(5) Uani d 1 . .
H H8 0.678451 0.401621 -0.016443 0.041 Uiso calc 1 . .
C C9 1.0770(6) 0.0505(2) 0.04336(19) 0.0276(5) Uani d 1 . .
H H9 1.245280 0.032279 0.089414 0.033 Uiso calc 1 . .
I I1 0.70611(17) 0.71086(4) 0.28588(4) 0.02737(9) Uani d 0.889(2) A 1
Cl Cl3 0.715(6) 0.7348(16) 0.3050(14) 0.0311(19) Uani d 0.111(2) A 2
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N1 I1 . . 105.59(15) ?
C4 N1 Cl3 . . 103.7(4) ?
C8 N1 C4 . . 116.7(2) ?
C8 N1 I1 . . 135.85(17) ?
C8 N1 Cl3 . . 138.0(4) ?
C2 C1 Cl1 . . 119.01(17) ?
C2 C1 C3 . 2_676 121.55(19) ?
C3 C1 Cl1 2_676 . 119.44(16) ?
C1 C2 Cl2 . . 119.08(16) ?
C1 C2 C3 . . 120.8(2) ?
C3 C2 Cl2 . . 120.13(16) ?
C1 C3 C2 2_676 . 117.65(19) ?
C1 C3 I1 2_676 . 121.43(15) ?
C1 C3 Cl3 2_676 . 121.0(7) ?
C2 C3 I1 . . 120.91(16) ?
C2 C3 Cl3 . . 121.3(7) ?
N1 C4 H4 . . 118.3 ?
N1 C4 C5 . . 123.4(2) ?
C5 C4 H4 . . 118.3 ?
C4 C5 H5 . . 120.0 ?
C4 C5 C6 . . 119.9(2) ?
C6 C5 H5 . . 120.0 ?
C5 C6 C7 . . 116.9(2) ?
C5 C6 C9 . . 119.5(2) ?
C7 C6 C9 . . 123.6(2) ?
C6 C7 H7 . . 120.4 ?
C8 C7 C6 . . 119.1(2) ?
C8 C7 H7 . . 120.4 ?
N1 C8 C7 . . 123.9(2) ?
N1 C8 H8 . . 118.0 ?
C7 C8 H8 . . 118.0 ?
C6 C9 H9 . . 117.1 ?
C9 C9 C6 2_755 . 125.7(3) ?
C9 C9 H9 2_755 . 117.1 ?
C3 I1 N1 . . 170.11(8) ?
C3 Cl3 N1 . . 170.7(11) ?
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
Cl1 C1 . 1.730(2) ?
Cl2 C2 . 1.729(2) ?
N1 C4 . 1.339(3) ?
N1 C8 . 1.331(3) ?
N1 I1 . 2.887(2) ?
N1 Cl3 . 3.144(16) ?
C1 C2 . 1.396(3) ?
C1 C3 2_676 1.397(3) ?
C2 C3 . 1.399(3) ?
C3 I1 . 2.092(2) ?
C3 Cl3 . 1.832(16) ?
C4 H4 . 0.9400 ?
C4 C5 . 1.381(3) ?
C5 H5 . 0.9400 ?
C5 C6 . 1.390(3) ?
C6 C7 . 1.392(3) ?
C6 C9 . 1.473(3) ?
C7 H7 . 0.9400 ?
C7 C8 . 1.392(3) ?
C8 H8 . 0.9400 ?
C9 C9 2_755 1.321(5) ?
C9 H9 . 0.9400 ?
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
Cl1 C1 C2 Cl2 . . . . 0.8(3) ?
Cl1 C1 C2 C3 . . . . -179.79(16) ?
Cl2 C2 C3 C1 . . . 2_676 179.65(16) ?
Cl2 C2 C3 I1 . . . . -0.9(3) ?
Cl2 C2 C3 Cl3 . . . . -4.6(8) ?
N1 C4 C5 C6 . . . . -1.5(4) ?
C1 C2 C3 C1 . . . 2_676 0.2(3) ?
C1 C2 C3 I1 . . . . 179.69(16) ?
C1 C2 C3 Cl3 . . . . 176.0(8) ?
C3 C1 C2 Cl2 2_676 . . . -179.67(16) ?
C3 C1 C2 C3 2_676 . . . -0.2(4) ?
C4 N1 C8 C7 . . . . 0.7(4) ?
C4 C5 C6 C7 . . . . 1.6(3) ?
C4 C5 C6 C9 . . . . -178.7(2) ?
C5 C6 C7 C8 . . . . -0.7(3) ?
C5 C6 C9 C9 . . . 2_755 161.1(3) ?
C6 C7 C8 N1 . . . . -0.5(4) ?
C7 C6 C9 C9 . . . 2_755 -19.2(4) ?
C8 N1 C4 C5 . . . . 0.3(4) ?
C9 C6 C7 C8 . . . . 179.6(2) ?
I1 N1 C4 C5 . . . . 167.2(2) ?
I1 N1 C8 C7 . . . . -161.03(19) ?
Cl3 N1 C4 C5 . . . . 168.4(5) ?
Cl3 N1 C8 C7 . . . . -161.8(6) ?
