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_7243954
_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, C10 H8 N4'
_chemical_formula_sum            'C16 H8 Cl5 I N4'
_chemical_formula_weight         560.41
_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             2021-06-23
_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                111.5100(10)
_cell_angle_beta                 93.2050(10)
_cell_angle_gamma                91.8070(10)
_cell_formula_units_Z            1
_cell_length_a                   3.91440(10)
_cell_length_b                   10.69090(10)
_cell_length_c                   12.4925(2)
_cell_measurement_reflns_used    9834
_cell_measurement_temperature    290.00(10)
_cell_measurement_theta_max      76.8540
_cell_measurement_theta_min      3.7840
_cell_volume                     484.858(16)
_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 0.989
_diffrn_measured_fraction_theta_max 0.935
_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  90.00  190
  2  \w     26.00 121.00   0.50    0.11    --   48.16  77.00  30.00  190
  3  \w     26.00 121.00   0.50    0.11    --   48.16  77.00-180.00  190
  4  \w    -64.00 -19.00   0.50    0.44    --  -91.75  57.00-180.00   90
  5  \w    -24.00  27.00   0.50    0.11    --  -48.16  19.00-180.00  102
  6  \w    -24.00  27.00   0.50    0.11    --  -48.16  19.00-120.00  102
  7  \w    -24.00  27.00   0.50    0.11    --  -48.16  19.00 -60.00  102
  8  \w    -24.00  27.00   0.50    0.11    --  -48.16  19.00 -30.00  102
  9  \w     35.00 106.00   0.50    0.44    --  107.78 -99.00  90.00  142
 10  \w     35.00 107.00   0.50    0.44    --  107.78-105.00 165.00  144
 11  \w     18.00  85.00   0.50    0.11    --   48.16-105.00 165.00  134
 12  \w     35.00 106.00   0.50    0.44    --  107.78 -99.00  30.00  142
 13  \w     35.00 106.00   0.50    0.44    --  107.78 -99.00   0.00  142
 14  \w     35.00  68.00   0.50    0.44    --  107.78 -57.00-180.00   66
 15  \w     35.00 107.00   0.50    0.44    --  107.78 -77.00 -60.00  144
 16  \w     35.00  68.00   0.50    0.44    --  107.78 -57.00   0.00   66
 17  \w     35.00  68.00   0.50    0.44    --  107.78 -57.00  30.00   66
 18  \w     35.00  68.00   0.50    0.44    --  107.78 -57.00  90.00   66
 19  \w     35.00 107.00   0.50    0.44    --  107.78 -77.00 150.00  144
 20  \w    105.00 178.00   0.50    0.44    --  107.78 105.00 -95.00  146
 21  \w     93.00 178.00   0.50    0.44    --  107.78  57.00-120.00  170
 22  \w     95.00 178.00   0.50    0.44    --  107.78  38.00-180.00  166
 23  \w     95.00 178.00   0.50    0.44    --  107.78  38.00-150.00  166
 24  \w    -85.00 -19.00   0.50    0.44    --  -91.75 125.00-150.00  132
 25  \w    -85.00 -19.00   0.50    0.44    --  -91.75 125.00 -90.00  132
 26  \w    -81.00 -19.00   0.50    0.44    --  -91.75 105.00 -95.00  124
 27  \w    -81.00   3.00   0.50    0.11    --  -48.16 105.00 -95.00  168
 28  \w   -121.00 -25.00   0.50    0.11    --  -48.16 -77.00 -60.00  192
 29  \w   -120.00 -33.00   0.50    0.11    --  -48.16 -57.00   0.00  174
 30  \w   -120.00 -33.00   0.50    0.11    --  -48.16 -57.00-120.00  174
 31  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00-180.00  188
 32  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00-150.00  188
 33  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00-120.00  188
 34  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 -60.00  188
 35  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 -30.00  188
 36  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00  30.00  188
 37  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00  60.00  188
 38  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 120.00  188
 39  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 150.00  188
 40  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00  90.00  188
 41  \w   -166.00 -79.00   0.50    0.44    --  -91.75 -19.00   0.00  174
 42  \w   -166.00 -79.00   0.50    0.44    --  -91.75 -19.00 -60.00  174
 43  \w   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 -90.00  188
 44  \w   -121.00 -73.00   0.50    0.11    --  -48.16-125.00-150.00   96
 45  \w   -121.00 -73.00   0.50    0.11    --  -48.16-125.00 -90.00   96
 46  \w   -163.00 -73.00   0.50    0.44    --  -91.75-125.00 -30.00  180
 47  \w   -163.00 -83.00   0.50    0.44    --  -91.75-105.00 165.00  160
;
_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      0.0671301000
_diffrn_orient_matrix_UB_12      -0.0410580000
_diffrn_orient_matrix_UB_13      0.1050012000
_diffrn_orient_matrix_UB_21      0.1264250000
_diffrn_orient_matrix_UB_22      0.1458462000
_diffrn_orient_matrix_UB_23      0.0739376000
_diffrn_orient_matrix_UB_31      -0.3679352000
_diffrn_orient_matrix_UB_32      0.0332975000
_diffrn_orient_matrix_UB_33      0.0342152000
_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  0.0490
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       4
_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            10832
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.039
_diffrn_reflns_theta_min         3.813
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    19.394
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.189
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_description       plate
_exptl_crystal_F_000             270
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene'
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0049(6)
_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   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1902
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0272
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.1162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0758
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1830
_reflns_number_total             1902
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01194d2.cif
_cod_data_source_block           C6ICl5_AP
_cod_depositor_comments
'Adding full bibliography for 7243952--7243955.cif.'
_cod_database_code               7243954
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16  H8  I1  Cl5  N4  '
_chemical_oxdiff_usercomment     'C6Cl5I + Azo'
_shelx_estimated_absorpt_t_max   0.526
_shelx_estimated_absorpt_t_min   0.119
_reflns_odcompleteness_completeness 98.90
_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. Rigid body (RIGU) restrains
 N2A, N2B, C7, C6, C8, N1, C4, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(N2B)=1-FVAR(1)
 Sof(N2A)=FVAR(1)
 Fixed Sof: I1(0.5) Cl1(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
;
_shelx_res_checksum              95247
_shelx_hkl_checksum              86098
_olex2_exptl_crystal_mounting_method 'MiTeGen 75 micron MicroLoop'
_olex2_submission_original_sample_id gro21_20
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.474
_oxdiff_exptl_absorpt_empirical_full_min 0.666