Preference of halogen bonds over hydrogen bonds within a discrete three-component co-crystal that undergo a [2+2] cycloaddition reaction
Powell, Conrad J.; Bosch, Eric; Krueger, Herman R.; Groeneman, Ryan H.; New Journal of Chemistry 47 (2023) 13084–13087; doi:10.1039/D3NJ02449K

data_7062520
_publ_section_title
;
 Preference of halogen bonds over hydrogen bonds within a discrete
 three-component co-crystal that undergo a [2+2] cycloaddition reaction
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13084
_journal_page_last               13087
_journal_paper_doi               10.1039/D3NJ02449K
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C12 H10 N2, 2(C6 H Cl4 I)'
_chemical_formula_sum            'C24 H12 Cl8 I2 N2'
_chemical_formula_weight         865.805
_chemical_name_systematic
'(E)-1,2-bis(4-pyridyl)ethene and 1,2,4,5-tetrachloro-3-iodobenzene cocrystal'
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-05-23 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.484(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.0650(1)
_cell_length_b                   11.0283(2)
_cell_length_c                   32.1854(6)
_cell_measurement_reflns_used    8144
_cell_measurement_temperature    299.36(13)
_cell_measurement_theta_max      78.6970
_cell_measurement_theta_min      2.7440
_cell_volume                     1442.39(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.36(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9926
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     48.00  73.00   0.50    0.42    --  111.50-125.00 120.00   50
  2  \w     84.00 111.00   0.50    0.42    --  111.50-125.00 120.00   54
  3  \w     68.00  98.00   0.50    0.42    --  111.50-125.00  60.00   60
  4  \w     56.00 100.00   0.50    0.42    --  111.50 -95.00 120.00   88
  5  \w     40.00 104.00   0.50    0.42    --  111.50 -95.00 150.00  128
  6  \w     48.00  73.00   0.50    0.42    --  111.50 -95.00  90.00   50
  7  \w     55.00  81.00   0.50    0.42    --  111.50 -95.00 -90.00   52
  8  \w     75.00 105.00   0.50    0.42    --  111.50 -95.00-120.00   60
  9  \w     58.00  84.00   0.50    0.42    --  111.50 -95.00-150.00   52
 10  \w     43.00  71.00   0.50    0.42    --  111.50 -61.00-120.00   56
 11  \w     44.00  73.00   0.50    0.42    --  111.50 -61.00-180.00   58
 12  \w     43.00  75.00   0.50    0.42    --  111.50 -61.00 -30.00   64
 13  \w     42.00  76.00   0.50    0.42    --  111.50 -61.00  30.00   68
 14  \w     40.00  76.00   0.50    0.42    --  111.50 -61.00  90.00   72
 15  \w     57.00  84.00   0.50    0.42    --  111.50 -77.00 150.00   54
 16  \w     92.00 117.00   0.50    0.42    --  111.50 -80.00 150.34   50
 17  \w      5.00  33.00   0.50    0.11    --   48.90 -25.00-175.00   56
 18  \w    -22.00  48.00   0.50    0.11    --   48.90 -38.00  60.00  140
 19  \w    131.00 171.00   0.50    0.42    --  111.50 125.00-180.00   80
 20  \w    118.00 149.00   0.50    0.42    --  111.50 125.00 -60.00   62
 21  \w    117.00 172.00   0.50    0.42    --  111.50  77.00 -90.00  110
 22  \w    101.00 175.00   0.50    0.42    --  111.50  45.00-150.00  148
 23  \w    112.00 137.00   0.50    0.42    --  111.50  77.00-180.00   50
 24  \w    112.00 159.00   0.50    0.42    --  111.50  45.00-120.00   94
 25  \w    144.00 169.00   0.50    0.42    --  111.50  77.00-120.00   50
 26  \w    114.00 140.00   0.50    0.42    --  111.50  77.00-120.00   52
 27  \w    118.00 143.00   0.50    0.42    --  111.50  61.00 -60.00   50
 28  \w     43.00  93.00   0.50    0.11    --   48.90  25.00 -11.00  100
 29  \w    109.00 161.00   0.50    0.42    --  111.50  30.00 -60.00  104
 30  \w    101.00 163.00   0.50    0.42    --  111.50  30.00 -30.00  124
 31  \w    116.00 152.00   0.50    0.42    --  111.50  45.00   0.00   72
 32  \w    139.00 174.00   0.50    0.42    --  111.50  25.00 -11.00   70
 33  \w    -26.00  24.00   0.50    0.11    --  -48.90  25.00 -11.00  100
 34  \w    -81.00 -44.00   0.50    0.11    --  -48.90 125.00-180.00   74
 35  \w    -45.00 -18.00   0.50    0.42    --  -90.00  45.00-150.00   54
 36  \w   -116.00 -46.00   0.50    0.11    --  -48.90 -25.00-175.00  140
 37  \w   -145.00-120.00   0.50    0.42    --  -90.00 -25.00-175.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2215478000
_diffrn_orient_matrix_UB_12      -0.0029845000
_diffrn_orient_matrix_UB_13      -0.0395589000
_diffrn_orient_matrix_UB_21      0.2918872000
_diffrn_orient_matrix_UB_22      -0.0459565000
_diffrn_orient_matrix_UB_23      -0.0251638000
_diffrn_orient_matrix_UB_31      -0.0974642000
_diffrn_orient_matrix_UB_32      -0.1318833000
_diffrn_orient_matrix_UB_33      0.0096723000
_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  0.0497
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.9988
_diffrn_reflns_Laue_measured_fraction_max 0.9926
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            14136
_diffrn_reflns_point_group_measured_fraction_full 0.9988
_diffrn_reflns_point_group_measured_fraction_max 0.9926
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         79.60
_diffrn_reflns_theta_min         4.24
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    24.107
_exptl_absorpt_correction_T_max  0.543
_exptl_absorpt_correction_T_min  0.103
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.994
_exptl_crystal_description       block
_exptl_crystal_F_000             832.222
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.3083
_refine_diff_density_min         -0.7349
_refine_diff_density_rms         0.1160
_refine_ls_d_res_high            0.7838
_refine_ls_d_res_low             10.4325
_refine_ls_goodness_of_fit_ref   1.0334
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3100
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0332
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          -0.0010
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+1.3887P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1200
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              40
_reflns_limit_l_min              0
_reflns_number_gt                2819
_reflns_number_total             3100
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3nj02449k2.cif
_cod_data_source_block           1_eb_a_156_2
_cod_depositor_comments
'Adding full bibliography for 7062520--7062522.cif.'
_cod_database_code               7062520
_chemical_oxdiff_formula         'C22 H12 Cl8 I2 N2'
_chemical_oxdiff_usercomment     'cut rod'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C3-C6A
 1.49 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C6) = Uanis(C6A)
4. Others
 Sof(C6A)=Sof(H6A)=1-FVAR(1)
 Sof(C6)=Sof(H6)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C10(H10), C6A(H6A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.786