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_7243952
_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 I1'
_chemical_formula_sum            'C6 Cl5 I'
_chemical_formula_weight         376.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                90
_cell_angle_beta                 92.013(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1229(2)
_cell_length_b                   3.91380(10)
_cell_length_c                   15.0718(4)
_cell_measurement_reflns_used    5231
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.7300
_cell_measurement_theta_min      5.7960
_cell_volume                     478.86(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      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.943
_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    -46.00  24.00   0.50    0.34    --  -47.91  43.00-113.00  140
  2  \w   -120.00 -34.00   0.50    0.34    --  -47.91 -43.00  94.00  172
  3  \w     36.00 120.00   0.50    0.34    --   47.91  43.00-113.00  168
  4  \w    -24.00  50.00   0.50    0.34    --   47.91 -43.00  94.00  148
  5  \w   -164.00 -78.00   0.50    1.35    --  -91.75 -43.00  94.00  172
  6  \w    -46.00 -19.00   0.50    1.35    --  -91.75  43.00-113.00   54
  7  \w     94.00 178.00   0.50    1.35    --  107.78  43.00-113.00  168
  8  \w   -119.00 -25.00   0.50    0.34    --  -47.91 -77.00  30.00  188
  9  \w    -24.00  28.00   0.50    0.34    --  -47.91  19.00  30.00  104
 10  \w    -24.00  28.00   0.50    0.34    --  -47.91  19.00-120.00  104
 11  \w   -163.00 -77.00   0.50    1.35    --  -91.75 -56.00 -44.46  172
 12  \w   -163.00 -69.00   0.50    1.35    --  -91.75 -77.00  30.00  188
 13  \w   -163.00 -69.00   0.50    1.35    --  -91.75 -76.00  41.73  188
 14  \w   -163.00 -78.00   0.50    1.35    --  -91.75 -50.00 -20.92  170
 15  \w    -64.00 -19.00   0.50    1.35    --  -91.75  57.00  60.00   90
 16  \w   -163.00 -77.00   0.50    1.35    --  -91.75 -54.00  -6.62  172
 17  \w   -163.00 -77.00   0.50    1.35    --  -91.75 -55.00 -38.84  172
 18  \w   -103.00 -19.00   0.50    1.35    --  -91.75  77.00  90.00  168
 19  \w   -163.00 -69.00   0.50    1.35    --  -91.75 -77.00   0.00  188
 20  \w   -163.00 -77.00   0.50    1.35    --  -91.75 -57.00  60.00  172
 21  \w    -64.00 -19.00   0.50    1.35    --  -91.75  57.00  90.00   90
 22  \w    -64.00 -19.00   0.50    1.35    --  -91.75  57.00   0.00   90
 23  \w   -163.00 -76.00   0.50    1.35    --  -91.75 -60.00 -11.47  174
 24  \w     35.00  68.00   0.50    1.35    --  107.78 -57.00 -60.00   66
 25  \w     35.00  68.00   0.50    1.35    --  107.78 -57.00  90.00   66
 26  \w     35.00 106.00   0.50    1.35    --  107.78 -99.00-180.00  142
 27  \w     35.00 106.00   0.50    1.35    --  107.78 -99.00 150.00  142
 28  \w     35.00 106.00   0.50    1.35    --  107.78 -99.00 -90.00  142
 29  \w     35.00 107.00   0.50    1.35    --  107.78 -77.00-180.00  144
 30  \w   -119.00 -73.00   0.50    0.34    --  -47.91-125.00-180.00   92
 31  \w   -119.00 -33.00   0.50    0.34    --  -47.91 -57.00-120.00  172
 32  \w   -119.00 -33.00   0.50    0.34    --  -47.91 -57.00  90.00  172
 33  \w     25.00 121.00   0.50    0.34    --   47.91  77.00 -60.00  192
 34  \w     25.00 121.00   0.50    0.34    --   47.91  77.00 150.00  192
 35  \w   -163.00-132.00   0.50    1.35    --  -91.75 -73.00 161.00   62
 36  \w     95.00 178.00   0.50    1.35    --  107.78  19.00-180.00  166
;
_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      -0.1369145000
_diffrn_orient_matrix_UB_12      -0.2096482000
_diffrn_orient_matrix_UB_13      -0.0478673000
_diffrn_orient_matrix_UB_21      0.0896060000
_diffrn_orient_matrix_UB_22      0.0357145000
_diffrn_orient_matrix_UB_23      -0.0879417000
_diffrn_orient_matrix_UB_31      0.0961285000
_diffrn_orient_matrix_UB_32      -0.3312422000
_diffrn_orient_matrix_UB_33      0.0208488000
_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  0.0437
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6562
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.974
_diffrn_reflns_theta_min         5.875
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    38.608
_exptl_absorpt_correction_T_max  0.535
_exptl_absorpt_correction_T_min  0.168
_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    2.609
_exptl_crystal_description       irregular
_exptl_crystal_F_000             348
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene'
_exptl_crystal_size_max          0.084
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.0013(2)
_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   1.112
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         946
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0260
_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^)+(0.0298P)^2^+0.7779P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                892
_reflns_number_total             946
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01194d2.cif
_cod_data_source_block           C6ICl5
_cod_depositor_comments
'Adding full bibliography for 7243952--7243955.cif.'
_cod_database_code               7243952
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12  Cl10  I2  '
_chemical_oxdiff_usercomment     'vial 4'
_shelx_estimated_absorpt_t_max   0.381
_shelx_estimated_absorpt_t_min   0.140
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Restrained distances
 C1-Cl3 = C3-Cl2 = C2-Cl1
 1.74392 with sigma of 0.02
 C1-I1 = C2-I2 = C3-I3
 1.93416 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(I2)
Uanis(Cl2) = Uanis(I3)
3. Rigid body (RIGU) restrains
 C1, C2, C3, I1, I2, I3, Cl1, Cl2, Cl3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 1*[Sof(I1)+Sof(Cl3)]+1*[Sof(Cl1)+Sof(I2)]+1*[Sof(Cl2)+Sof(I3)]=0.5 with esd
 of 0
 Sof(Cl3)=1-FVAR(1)
 Sof(I1)=FVAR(1)
 Sof(Cl1)=1-FVAR(2)
 Sof(I2)=FVAR(2)
 Sof(Cl2)=1-FVAR(3)
 Sof(I3)=FVAR(3)
;
_shelx_res_checksum              59519
_shelx_hkl_checksum              93985
_olex2_exptl_crystal_mounting_method
'Hampton Research 20 micron nylon CryoLoop'
_olex2_submission_original_sample_id gro21_23
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   284
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.507
_oxdiff_exptl_absorpt_empirical_full_min 0.657