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_7062521
_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         '2(C6 H Cl4 I), C12 H8 N2'
_chemical_formula_sum            'C24 H10 Cl8 I2 N2'
_chemical_formula_weight         863.789
_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             2023-05-23
_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                 91.831(1)
_cell_angle_gamma                90
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_cell_length_b                   11.2938(1)
_cell_length_c                   31.5449(4)
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_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
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_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.06(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9942
_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     43.00  76.00   0.50    0.15    --  111.50 -61.00-150.00   66
  2  \w     71.00  96.00   0.50    0.15    --  111.50 -77.00  30.00   50
  3  \w     51.00  76.00   0.50    0.15    --  111.50 -61.00  60.00   50
  4  \w     63.00 108.00   0.50    0.15    --  111.50 -77.00  90.00   90
  5  \w     66.00  92.00   0.50    0.15    --  111.50 -77.00 120.00   52
  6  \w     41.00  76.00   0.50    0.15    --  111.50 -61.00 120.00   70
  7  \w     49.00  74.00   0.50    0.15    --  111.50 -61.00  30.00   50
  8  \w     47.00  75.00   0.50    0.15    --  111.50 -61.00 -30.00   56
  9  \w     49.00  74.00   0.50    0.15    --  111.50 -61.00 -60.00   50
 10  \w     40.00  72.00   0.50    0.15    --  111.50 -61.00-120.00   64
 11  \w     50.00  86.00   0.50    0.15    --  111.50 -95.00 -60.00   72
 12  \w     86.00 111.00   0.50    0.15    --  111.50-125.00-120.00   50
 13  \w     66.00 109.00   0.50    0.15    --  111.50-125.00-150.00   86
 14  \w     54.00  97.00   0.50    0.15    --  111.50-125.00-180.00   86
 15  \w     50.00  75.00   0.50    0.15    --  111.50 -95.00-150.00   50
 16  \w     40.00 101.00   0.50    0.15    --  111.50 -95.00  30.00  122
 17  \w    116.00 142.00   0.50    0.15    --  111.50  15.00 -60.00   52
 18  \w    153.00 178.00   0.50    0.15    --  111.50  77.00  90.00   50
 19  \w    142.00 176.00   0.50    0.15    --  111.50  45.00  60.00   68
 20  \w    102.00 130.00   0.50    0.15    --  111.50  45.00  60.00   56
 21  \w    103.00 169.00   0.50    0.15    --  111.50  45.00   0.00  132
 22  \w    124.00 150.00   0.50    0.15    --  111.50  45.00 150.00   52
 23  \w    144.00 172.00   0.50    0.15    --  111.50  77.00   0.00   56
 24  \w    120.00 178.00   0.50    0.15    --  111.50  32.00  35.00  116
 25  \w     56.00  81.00   0.50    0.05    --   48.90  32.00  35.00   50
 26  \w    101.00 133.00   0.50    0.15    --  111.50  30.00 150.00   64
 27  \w    106.00 166.00   0.50    0.15    --  111.50  61.00 -60.00  120
 28  \w    102.00 133.00   0.50    0.15    --  111.50  30.00 -30.00   62
 29  \w    109.00 135.00   0.50    0.15    --  111.50  30.00 -60.00   52
 30  \w    111.00 136.00   0.50    0.15    --  111.50  45.00-120.00   50
 31  \w    135.00 161.00   0.50    0.15    --  111.50  45.00-180.00   52
 32  \w    101.00 127.00   0.50    0.15    --  111.50  30.00-180.00   52
 33  \w    113.00 138.00   0.50    0.15    --  111.50 125.00 -60.00   50
 34  \w    153.00 178.00   0.50    0.15    --  111.50 125.00 -60.00   50
 35  \w    -14.00  11.00   0.50    0.05    --   48.90 -32.00-123.00   50
 36  \w     -8.00  25.00   0.50    0.05    --  -48.90  19.00  60.00   66
 37  \w    -32.00  -7.00   0.50    0.05    --  -48.90  32.00  35.00   50
 38  \w    -80.00 -55.00   0.50    0.05    --  -48.90 125.00-180.00   50
 39  \w    -44.00 -18.00   0.50    0.15    --  -90.00  45.00-150.00   52
 40  \w    -37.00  23.00   0.50    0.05    --  -48.90  38.00-180.00  120
 41  \w   -122.00 -40.00   0.50    0.05    --  -48.90 -32.00-123.00  164
 42  \w   -145.00-120.00   0.50    0.15    --  -90.00 -32.00-123.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0596685000
_diffrn_orient_matrix_UB_12      0.0402368000
_diffrn_orient_matrix_UB_13      0.0462788000
_diffrn_orient_matrix_UB_21      -0.3565330000
_diffrn_orient_matrix_UB_22      -0.0383664000
_diffrn_orient_matrix_UB_23      0.0103251000
_diffrn_orient_matrix_UB_31      0.1291181000
_diffrn_orient_matrix_UB_32      -0.1245548000
_diffrn_orient_matrix_UB_33      0.0117638000
_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  0.0451
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.9942
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            14488
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9942
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         79.77
_diffrn_reflns_theta_min         2.80
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    24.313
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    2.006
_exptl_crystal_description       block
_exptl_crystal_F_000             828.223
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
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_refine_diff_density_rms         0.1171
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_refine_ls_d_res_low             15.7644
_refine_ls_goodness_of_fit_ref   1.0274
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    10
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0274
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+1.2404P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0893
_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                2900
_reflns_number_total             3089
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3nj02449k2.cif
_cod_data_source_block           eb_a_159_2_auto
_cod_depositor_comments
'Adding full bibliography for 7062520--7062522.cif.'
_cod_database_code               7062521
_chemical_oxdiff_formula         'C24 H10 Cl8 I2 N2'
_chemical_oxdiff_usercomment     'cut block'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C2(H2), C4(H4), C3(H3)
;
_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 1.849
_oxdiff_exptl_absorpt_empirical_full_min 0.696