#------------------------------------------------------------------------------
#$Date: 2022-01-06 23:12:42 +0200 (Thu, 06 Jan 2022) $
#$Revision: 271828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/39/7243954.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7243954
loop_
_publ_author_name
'Shapiro, Nicole M.'
'Bosch, Eric'
'Unruh, Daniel K.'
'Krueger, Herman R.'
'Groeneman, Ryan H.'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00 121.00   0.50    0.11    --   48.16  77.00  90.00  190
  2  ω     26.00 121.00   0.50    0.11    --   48.16  77.00  30.00  190
  3  ω     26.00 121.00   0.50    0.11    --   48.16  77.00-180.00  190
  4  ω    -64.00 -19.00   0.50    0.44    --  -91.75  57.00-180.00   90
  5  ω    -24.00  27.00   0.50    0.11    --  -48.16  19.00-180.00  102
  6  ω    -24.00  27.00   0.50    0.11    --  -48.16  19.00-120.00  102
  7  ω    -24.00  27.00   0.50    0.11    --  -48.16  19.00 -60.00  102
  8  ω    -24.00  27.00   0.50    0.11    --  -48.16  19.00 -30.00  102
  9  ω     35.00 106.00   0.50    0.44    --  107.78 -99.00  90.00  142
 10  ω     35.00 107.00   0.50    0.44    --  107.78-105.00 165.00  144
 11  ω     18.00  85.00   0.50    0.11    --   48.16-105.00 165.00  134
 12  ω     35.00 106.00   0.50    0.44    --  107.78 -99.00  30.00  142
 13  ω     35.00 106.00   0.50    0.44    --  107.78 -99.00   0.00  142
 14  ω     35.00  68.00   0.50    0.44    --  107.78 -57.00-180.00   66
 15  ω     35.00 107.00   0.50    0.44    --  107.78 -77.00 -60.00  144
 16  ω     35.00  68.00   0.50    0.44    --  107.78 -57.00   0.00   66
 17  ω     35.00  68.00   0.50    0.44    --  107.78 -57.00  30.00   66
 18  ω     35.00  68.00   0.50    0.44    --  107.78 -57.00  90.00   66
 19  ω     35.00 107.00   0.50    0.44    --  107.78 -77.00 150.00  144
 20  ω    105.00 178.00   0.50    0.44    --  107.78 105.00 -95.00  146
 21  ω     93.00 178.00   0.50    0.44    --  107.78  57.00-120.00  170
 22  ω     95.00 178.00   0.50    0.44    --  107.78  38.00-180.00  166
 23  ω     95.00 178.00   0.50    0.44    --  107.78  38.00-150.00  166
 24  ω    -85.00 -19.00   0.50    0.44    --  -91.75 125.00-150.00  132
 25  ω    -85.00 -19.00   0.50    0.44    --  -91.75 125.00 -90.00  132
 26  ω    -81.00 -19.00   0.50    0.44    --  -91.75 105.00 -95.00  124
 27  ω    -81.00   3.00   0.50    0.11    --  -48.16 105.00 -95.00  168
 28  ω   -121.00 -25.00   0.50    0.11    --  -48.16 -77.00 -60.00  192
 29  ω   -120.00 -33.00   0.50    0.11    --  -48.16 -57.00   0.00  174
 30  ω   -120.00 -33.00   0.50    0.11    --  -48.16 -57.00-120.00  174
 31  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00-180.00  188
 32  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00-150.00  188
 33  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00-120.00  188
 34  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 -60.00  188
 35  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 -30.00  188
 36  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00  30.00  188
 37  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00  60.00  188
 38  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 120.00  188
 39  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 150.00  188
 40  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00  90.00  188
 41  ω   -166.00 -79.00   0.50    0.44    --  -91.75 -19.00   0.00  174
 42  ω   -166.00 -79.00   0.50    0.44    --  -91.75 -19.00 -60.00  174
 43  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 -90.00  188
 44  ω   -121.00 -73.00   0.50    0.11    --  -48.16-125.00-150.00   96
 45  ω   -121.00 -73.00   0.50    0.11    --  -48.16-125.00 -90.00   96
 46  ω   -163.00 -73.00   0.50    0.44    --  -91.75-125.00 -30.00  180
 47  ω   -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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0449P)²+0.1162P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.2015(2) 0.71801(10) 0.78590(9) 0.04324(19) Uani 0.5 1 d . . P A 2
Cl1 Cl 1.1953(16) 0.7240(6) 0.7952(5) 0.091(3) Uani 0.5 1 d . . P A 1
Cl2 Cl 1.2738(2) 1.01490(8) 0.77553(5) 0.0602(2) Uani 1 1 d . . . . .
Cl3 Cl 1.0893(2) 1.27620(8) 0.96969(7) 0.0668(3) Uani 1 1 d . . . . .
C1 C 1.0844(7) 0.8816(3) 0.9114(2) 0.0458(6) Uani 1 1 d . . . . .
C2 C 1.1206(7) 1.0060(3) 0.8997(2) 0.0454(6) Uani 1 1 d . . . . .
C3 C 1.0376(7) 1.1234(3) 0.9872(2) 0.0474(6) Uani 1 1 d . . . . .
N1 N 0.6105(8) 0.5500(2) 0.3688(2) 0.0591(6) Uani 1 1 d . . . . .
C4 C 0.7127(9) 0.6376(3) 0.4737(3) 0.0557(7) Uani 1 1 d . . . . .
H4 H 0.816792 0.604834 0.526176 0.067 Uiso 1 1 calc R U . . .
C5 C 0.6724(8) 0.7751(3) 0.5091(2) 0.0496(6) Uani 1 1 d . . . . .
H5 H 0.747903 0.833232 0.583170 0.060 Uiso 1 1 calc R U . . .
C6 C 0.5163(7) 0.8230(2) 0.4308(2) 0.0450(5) Uani 1 1 d . . . . .
C7 C 0.4045(9) 0.7336(3) 0.3225(2) 0.0546(6) Uani 1 1 d . . . . .
H7 H 0.295958 0.762933 0.268500 0.066 Uiso 1 1 calc R U . . .
C8 C 0.4585(9) 0.5988(3) 0.2964(3) 0.0595(7) Uani 1 1 d . . . . .
H8 H 0.383199 0.538476 0.223165 0.071 Uiso 1 1 calc R U . . .
N2A N 0.4573(7) 0.9617(3) 0.4508(2) 0.0480(8) Uani 0.937(8) 1 d . . P B 1
N2B N 0.529(12) 0.964(5) 0.527(4) 0.055(9) Uani 0.063(8) 1 d . . P B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 2 0.0151
-2 3 -3 0.0535
0 4 -8 0.0169
0 6 0 0.0581
2 4 -1 0.0489
0 -6 -1 0.0649
-1 5 2 0.0662
-2 -1 -5 0.0519
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 119.78(19) . . ?
C2 C1 Cl1 121.3(3) . . ?
C2 C1 C3 118.8(2) . 2_777 ?
C3 C1 I1 121.4(2) 2_777 . ?
C3 C1 Cl1 119.9(3) 2_777 . ?
C1 C2 Cl2 119.7(2) . . ?
C3 C2 Cl2 119.5(2) . . ?
C3 C2 C1 120.9(2) . . ?
C1 C3 Cl3 120.2(2) 2_777 . ?
C2 C3 Cl3 119.4(2) . . ?
C2 C3 C1 120.3(3) . 2_777 ?
C8 N1 C4 117.0(2) . . ?
N1 C4 H4 118.2 . . ?
N1 C4 C5 123.6(3) . . ?
C5 C4 H4 118.2 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.9(3) . . ?
C6 C5 H5 121.1 . . ?
C5 C6 N2A 125.9(2) . . ?
C5 C6 N2B 88.6(19) . . ?
C7 C6 C5 119.3(2) . . ?
C7 C6 N2A 114.8(2) . . ?
C7 C6 N2B 151.5(19) . . ?
C6 C7 H7 121.0 . . ?
C6 C7 C8 117.9(3) . . ?
C8 C7 H7 121.0 . . ?
N1 C8 C7 124.3(3) . . ?
N1 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
N2A N2A C6 113.6(3) 2_676 . ?
N2B N2B C6 102(5) 2_676 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 1.961(3) . ?
Cl1 C1 1.859(7) . ?
Cl2 C2 1.728(2) . ?
Cl3 C3 1.733(3) . ?
C1 C2 1.393(4) . ?
C1 C3 1.397(4) 2_777 ?
C2 C3 1.391(4) . ?
N1 C4 1.331(4) . ?
N1 C8 1.323(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(4) . ?
C6 C7 1.377(4) . ?
C6 N2A 1.439(4) . ?
C6 N2B 1.54(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(4) . ?
C8 H8 0.9300 . ?
N2A N2A 1.222(6) 2_676 ?
N2B N2B 1.22(10) 2_676 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 Cl2 -0.8(3) . . . . ?
I1 C1 C2 C3 179.66(19) . . . . ?
Cl1 C1 C2 Cl2 -0.4(4) . . . . ?
Cl1 C1 C2 C3 -179.9(3) . . . . ?
Cl2 C2 C3 Cl3 0.1(3) . . . . ?
Cl2 C2 C3 C1 -179.5(2) . . . 2_777 ?
C1 C2 C3 Cl3 179.5(2) . . . . ?
C1 C2 C3 C1 -0.1(4) . . . 2_777 ?
C3 C1 C2 Cl2 179.54(19) 2_777 . . . ?
C3 C1 C2 C3 0.1(4) 2_777 . . . ?
N1 C4 C5 C6 0.2(5) . . . . ?
C4 N1 C8 C7 0.8(5) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C4 C5 C6 N2A -178.9(3) . . . . ?
C4 C5 C6 N2B 174.6(17) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C5 C6 N2A N2A -3.9(5) . . . 2_676 ?
C5 C6 N2B N2B 165(5) . . . 2_676 ?
C6 C7 C8 N1 0.1(5) . . . . ?
C7 C6 N2A N2A 176.5(3) . . . 2_676 ?
C7 C6 N2B N2B -26(8) . . . 2_676 ?
C8 N1 C4 C5 -1.0(5) . . . . ?
N2A C6 C7 C8 178.8(3) . . . . ?
N2B C6 C7 C8 -168(4) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -0.9988 1.9982 0.2508 0.0021 0.0351
-2.1563 3.4324 -2.8686 -0.5869 0.0159 0.8095
-0.0701 4.1842 -7.7906 -0.9945 0.0254 -0.1014
0.3975 6.1649 0.4210 -0.1822 0.9805 0.0734
2.0801 3.7181 -1.1574 -0.1345 0.7197 -0.6811
-0.0526 -6.1953 -0.6891 0.1785 -0.9612 -0.2105
-1.2454 5.1978 1.5670 -0.1325 0.7165 0.6849
-1.6849 -1.1327 -4.6077 -0.5504 -0.7189 0.4245
