Iodoperchlorobenzene acts as a dual halogen-bond donor to template a [2 + 2] cycloaddition reaction within an organic co-crystal
Shapiro, Nicole M.; Bosch, Eric; Unruh, Daniel K.; Krueger, Herman R.; Groeneman, Ryan H.; CrystEngComm 23 (2021) 8265–8268; doi:10.1039/D1CE01194D

data_7243955
_publ_section_title
;
 Iodoperchlorobenzene acts as a dual halogen-bond donor to template a [2 +
 2] cycloaddition reaction within an organic co-crystal
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              8265
_journal_page_last               8268
_journal_paper_doi               10.1039/D1CE01194D
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C6 Cl5 I, C12 H10 N2'
_chemical_formula_sum            'C18 H10 Cl5 I N2'
_chemical_formula_weight         558.43
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_audit_update_record
;
2021-08-31 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                111.056(2)
_cell_angle_beta                 93.327(2)
_cell_angle_gamma                93.491(2)
_cell_formula_units_Z            1
_cell_length_a                   3.97460(10)
_cell_length_b                   10.7984(2)
_cell_length_c                   12.4426(3)
_cell_measurement_reflns_used    9040
_cell_measurement_temperature    290.00(10)
_cell_measurement_theta_max      77.1690
_cell_measurement_theta_min      3.7930
_cell_volume                     495.61(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.938
_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     26.00 121.00   0.50    0.11    --   48.16  77.00-120.00  190
  2  \w     95.00 178.00   0.50    0.44    --  107.78  38.00-120.00  166
  3  \w     95.00 178.00   0.50    0.44    --  107.78  38.00 -90.00  166
  4  \w     26.00 121.00   0.50    0.11    --   48.16  77.00  60.00  190
  5  \w    101.00 178.00   0.50    0.44    --  107.78  86.00 131.00  154
  6  \w    -21.00  75.00   0.50    0.11    --   48.16 -86.00  13.00  192
  7  \w     35.00 112.00   0.50    0.44    --  107.78-125.00-120.00  154
  8  \w     35.00 106.00   0.50    0.44    --  107.78 -99.00 -60.00  142
  9  \w     35.00 106.00   0.50    0.44    --  107.78 -99.00   0.00  142
 10  \w     35.00 106.00   0.50    0.44    --  107.78 -99.00  30.00  142
 11  \w     35.00 106.00   0.50    0.44    --  107.78 -99.00 150.00  142
 12  \w     35.00 135.00   0.50    0.44    --  107.78 -86.00  13.00  200
 13  \w     35.00 107.00   0.50    0.44    --  107.78 -77.00 -90.00  144
 14  \w     35.00 107.00   0.50    0.44    --  107.78 -77.00-150.00  144
 15  \w     35.00  68.00   0.50    0.44    --  107.78 -57.00  60.00   66
 16  \w     35.00  68.00   0.50    0.44    --  107.78 -57.00  90.00   66
 17  \w     35.00  68.00   0.50    0.44    --  107.78 -57.00 150.00   66
 18  \w    -25.00  45.00   0.50    0.11    --   48.16 -38.00 120.00  140
 19  \w    -41.00  25.00   0.50    0.11    --  -48.16  38.00  30.00  132
 20  \w    -64.00 -19.00   0.50    0.44    --  -91.75  57.00 -60.00   90
 21  \w    -64.00 -19.00   0.50    0.44    --  -91.75  57.00 -30.00   90
 22  \w    -64.00 -19.00   0.50    0.44    --  -91.75  57.00   0.00   90
 23  \w    -64.00 -19.00   0.50    0.44    --  -91.75  57.00  60.00   90
 24  \w    -75.00  25.00   0.50    0.11    --  -48.16  86.00 131.00  200
 25  \w    -75.00  25.00   0.50    0.11    --  -48.16  86.00 131.00  200
 26  \w   -118.00 -19.00   0.50    0.44    --  -91.75  86.00 131.00  198
 27  \w   -121.00 -25.00   0.50    0.11    --  -48.16 -77.00 150.00  192
 28  \w   -121.00 -25.00   0.50    0.11    --  -48.16 -77.00  60.00  192
 29  \w   -121.00 -35.00   0.50    0.11    --  -48.16 -38.00 150.00  172
 30  \w   -120.00 -33.00   0.50    0.11    --  -48.16 -57.00 -30.00  174
 31  \w   -121.00 -25.00   0.50    0.11    --  -48.16 -77.00 -60.00  192
 32  \w   -120.00 -33.00   0.50    0.11    --  -48.16 -57.00-120.00  174
 33  \w   -163.00 -95.00   0.50    0.44    --  -91.75 -77.00-150.00  136
 34  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 -90.00  188
 35  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 -60.00  188
 36  \w   -163.00 -71.00   0.50    0.44    --  -91.75 -71.00 -29.55  184
 37  \w   -163.00 -70.00   0.50    0.44    --  -91.75 -74.00  18.60  186
 38  \w   -163.00 -74.00   0.50    0.44    --  -91.75 -63.00  55.76  178
 39  \w   -163.00 -74.00   0.50    0.44    --  -91.75 -63.00 150.58  178
 40  \w   -165.00 -78.00   0.50    0.44    --  -91.75 -38.00 150.00  174
 41  \w   -163.00 -77.00   0.50    0.44    --  -91.75 -57.00 120.00  172
 42  \w   -163.00 -77.00   0.50    0.44    --  -91.75 -57.00  90.00  172
 43  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00  60.00  188
 44  \w   -163.00 -77.00   0.50    0.44    --  -91.75 -57.00-150.00  172
 45  \w   -121.00 -73.00   0.50    0.11    --  -48.16-125.00-180.00   96
 46  \w   -163.00 -79.00   0.50    0.44    --  -91.75 -86.00  13.00  168
;
_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      -0.1215638000
_diffrn_orient_matrix_UB_12      -0.1482098000
_diffrn_orient_matrix_UB_13      -0.0331434000
_diffrn_orient_matrix_UB_21      0.1697837000
_diffrn_orient_matrix_UB_22      -0.0335060000
_diffrn_orient_matrix_UB_23      -0.1140904000
_diffrn_orient_matrix_UB_31      0.3291054000
_diffrn_orient_matrix_UB_32      -0.0215147000
_diffrn_orient_matrix_UB_33      0.0601453000
_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  0.0525
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11021
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.065
_diffrn_reflns_theta_min         3.821
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    18.940
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_correction_T_min  0.236
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_description       irregular
_exptl_crystal_F_000             270
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene'
_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+0.1238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1836
_reflns_number_total             1952
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01194d2.cif
_cod_data_source_block           C6ICl5_BPE
_cod_depositor_comments
'Adding full bibliography for 7243952--7243955.cif.'
_cod_database_code               7243955
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18  H10  I1  Cl5  N2  '
_chemical_oxdiff_usercomment     'C6Cl5I + BPE'
_shelx_estimated_absorpt_t_max   0.368
_shelx_estimated_absorpt_t_min   0.180
_reflns_odcompleteness_completeness 99.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: I1(0.5) Cl1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C9(H9)
;
_shelx_res_checksum              22738
_shelx_hkl_checksum              64559
_olex2_exptl_crystal_mounting_method 'MiTeGen 75 micro MicroLoop'
_olex2_submission_original_sample_id gro21_18
_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 2.145
_oxdiff_exptl_absorpt_empirical_full_min 0.568