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_7062522
_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         'C10 H8 N4, 2(C6 H Cl4 I)'
_chemical_formula_sum            'C22 H10 Cl8 I2 N4'
_chemical_formula_weight         867.781
_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     direct
_audit_creation_date             2023-04-10
_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                 91.490(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.0199(1)
_cell_length_b                   10.8882(3)
_cell_length_c                   32.3284(10)
_cell_measurement_reflns_used    7693
_cell_measurement_temperature    298.36(16)
_cell_measurement_theta_max      79.0370
_cell_measurement_theta_min      4.8800
_cell_volume                     1414.52(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.36(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.9782
_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    124.00 161.00   0.50    0.65    --  111.50 125.00-180.00   74
  2  \w    123.00 159.00   0.50    0.65    --  111.50 125.00  30.00   72
  3  \w    -34.00  11.00   0.50    0.16    --  -48.65  35.00 -80.00   90
  4  \w    -62.00 -35.00   0.50    0.65    --  -90.00  61.00  90.00   54
  5  \w    -20.00  21.00   0.50    0.16    --  -48.65  19.00  60.00   82
  6  \w     10.00  38.00   0.50    0.16    --   48.65 -35.00 122.00   56
  7  \w    122.00 157.00   0.50    0.65    --  111.50  77.00 -30.00   70
  8  \w    112.00 146.00   0.50    0.65    --  111.50  61.00-120.00   68
  9  \w    118.00 144.00   0.50    0.65    --  111.50  61.00-150.00   52
 10  \w    107.00 144.00   0.50    0.65    --  111.50  61.00-180.00   74
 11  \w    108.00 178.00   0.50    0.65    --  111.50  45.00 -60.00  140
 12  \w    103.00 136.00   0.50    0.65    --  111.50  45.00-150.00   66
 13  \w    102.00 127.00   0.50    0.65    --  111.50  45.00-120.00   50
 14  \w    130.00 156.00   0.50    0.65    --  111.50  35.00 -80.00   52
 15  \w    142.00 173.00   0.50    0.65    --  111.50  45.00 120.00   62
 16  \w    103.00 137.00   0.50    0.65    --  111.50  45.00 120.00   68
 17  \w    114.00 145.00   0.50    0.65    --  111.50  61.00 150.00   62
 18  \w    153.00 178.00   0.50    0.65    --  111.50  61.00 150.00   50
 19  \w    127.00 168.00   0.50    0.65    --  111.50  30.00 150.00   82
 20  \w     56.00  81.00   0.50    0.16    --   48.65  35.00 -80.00   50
 21  \w     40.00  65.00   0.50    0.65    --  111.50 -61.00 -30.00   50
 22  \w     44.00  82.00   0.50    0.65    --  111.50 -77.00-120.00   76
 23  \w     84.00 110.00   0.50    0.65    --  111.50 -77.00 -90.00   52
 24  \w     40.00  76.00   0.50    0.65    --  111.50 -61.00 -90.00   72
 25  \w     40.00  65.00   0.50    0.65    --  111.50 -61.00-150.00   50
 26  \w     62.00  88.00   0.50    0.65    --  111.50 -77.00 -30.00   52
 27  \w     42.00  67.00   0.50    0.65    --  111.50 -61.00   0.00   50
 28  \w     47.00  73.00   0.50    0.65    --  111.50 -77.00  30.00   52
 29  \w     46.00  71.00   0.50    0.65    --  111.50 -61.00  30.00   50
 30  \w     49.00  76.00   0.50    0.65    --  111.50 -61.00  90.00   54
 31  \w     43.00  68.00   0.50    0.65    --  111.50 -95.00  90.00   50
 32  \w     41.00  67.00   0.50    0.65    --  111.50 -95.00 120.00   52
 33  \w     69.00  99.00   0.50    0.65    --  111.50 -95.00 120.00   60
 34  \w     71.00  99.00   0.50    0.65    --  111.50 -95.00  90.00   56
 35  \w    102.00 128.00   0.50    0.65    --  111.50 -87.00   8.27   52
 36  \w     94.00 120.00   0.50    0.65    --  111.50 -84.00 148.34   52
 37  \w     53.00  82.00   0.50    0.65    --  111.50 -87.00   8.27   58
 38  \w     66.00  92.00   0.50    0.65    --  111.50 -95.00 -30.00   52
 39  \w     71.00 105.00   0.50    0.65    --  111.50 -95.00-120.00   68
 40  \w     49.00  76.00   0.50    0.65    --  111.50 -95.00-180.00   54
 41  \w   -101.00 -40.00   0.50    0.16    --  -48.65 -38.00  60.00  122
 42  \w    -97.00 -39.00   0.50    0.16    --  -48.65 -35.00 122.00  116
 43  \w   -121.00 -96.00   0.50    0.65    --  -90.00 -35.00 122.00   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      0.2567323000
_diffrn_orient_matrix_UB_12      0.0582957000
_diffrn_orient_matrix_UB_13      0.0302163000
_diffrn_orient_matrix_UB_21      0.2357962000
_diffrn_orient_matrix_UB_22      0.0222213000
_diffrn_orient_matrix_UB_23      -0.0360822000
_diffrn_orient_matrix_UB_31      -0.1593399000
_diffrn_orient_matrix_UB_32      0.1270312000
_diffrn_orient_matrix_UB_33      -0.0075703000
_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  0.0717
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.9961
_diffrn_reflns_Laue_measured_fraction_max 0.9782
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            12094
_diffrn_reflns_point_group_measured_fraction_full 0.9961
_diffrn_reflns_point_group_measured_fraction_max 0.9782
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         79.95
_diffrn_reflns_theta_min         2.73
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    24.605
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.974
_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 orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.037
_exptl_crystal_description       block
_exptl_crystal_F_000             832.276
_exptl_crystal_preparation       'from pure components'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.8540
_refine_diff_density_min         -1.4139
_refine_diff_density_rms         0.2646
_refine_ls_d_res_high            0.7829
_refine_ls_d_res_low             16.1587
_refine_ls_goodness_of_fit_ref   1.0388
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    15
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3011
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.0385
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0673
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0563P)^2^+21.0115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1769
_refine_ls_wR_factor_ref         0.1800
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              41
_reflns_limit_l_min              0
_reflns_number_gt                2690
_reflns_number_total             3011
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3nj02449k2.cif
_cod_data_source_block           3_eb_a_158_3
_cod_depositor_comments
'Adding full bibliography for 7062520--7062522.cif.'
_cod_database_code               7062522
_chemical_oxdiff_formula         'C24 H10 Cl8 I2 N4'
_chemical_oxdiff_usercomment     'cut block'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C5-N2
 1.43 with sigma of 0.02
 C5A-N2A
 1.43 with sigma of 0.02
3. Others
 Sof(N2A)=Sof(C5A)=1-FVAR(1)
 Sof(N2)=Sof(C5)=FVAR(1)
 Fixed Sof: H1a(0.5) H1b(0.5) H4a(0.5) H4b(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1a), C1(H1b), C2(H2), C3(H3), C4(H4a), C4(H4b), C9(H9)
;
_olex2_exptl_crystal_mounting_method 'in Paratone oil on a mitagen mount'
_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 2.101
_oxdiff_exptl_absorpt_empirical_full_min 0.452