Tetradentate halogen bonding macrocyclic anion receptor inspired by the "Texas-sized" molecular box.
Zhao, Tian; Lynch, Vincent M.; Sessler, Jonathan L.; Organic & biomolecular chemistry 20 (2022) 980–983; doi:10.1039/d1ob02381k

data_7158495
_publ_section_title
;
 Tetradentate halogen bonding macrocyclic anion receptor inspired by the
 "Texas-sized" molecular box.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              980
_journal_page_last               983
_journal_paper_doi               10.1039/d1ob02381k
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         '2(C22 H19 I2 N7 O2), C H Cl3'
_chemical_formula_sum            'C45 H39 Cl3 I4 N14 O4'
_chemical_formula_weight         1453.85
_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_block_doi                 10.5517/ccdc.csd.cc29cmw6
_audit_creation_date             2021-12-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2021-12-05 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                97.062(2)
_cell_angle_beta                 100.4278(18)
_cell_angle_gamma                115.900(3)
_cell_formula_units_Z            2
_cell_length_a                   13.4032(3)
_cell_length_b                   13.4811(6)
_cell_length_c                   19.0017(3)
_cell_measurement_reflns_used    21037
_cell_measurement_temperature    100.02(14)
_cell_measurement_theta_max      73.0800
_cell_measurement_theta_min      3.7050
_cell_volume                     2957.30(18)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Shelxtl-Plus/XP, Bruker AXS, Inc. 2009'
_computing_publication_material  'Shelxtl-Plus, Bruker AXS, Inc. 2009'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2940
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.965
_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   -116.00 -17.00   1.00    6.00    --  -41.59 -38.00 -30.00   99
  2  \w     24.00 100.00   1.00   24.00    --  107.09 -94.00 -60.00   76
  3  \w    -83.00  38.00   1.00    6.00    --  -41.59  19.00 150.00  121
  4  \w    103.00 178.00   1.00   24.00    --  107.09  77.00 -30.00   75
  5  \w    -87.00  -6.00   1.00    6.00    --  -41.59 125.00-150.00   81
  6  \w     34.00 112.00   1.00   24.00    --  107.09-125.00  90.00   78
  7  \w    -87.00  -6.00   1.00    6.00    --  -41.59 125.00 120.00   81
  8  \w    103.00 178.00   1.00   24.00    --  107.09  77.00 120.00   75
  9  \w     35.00 117.00   1.00   24.00    --  107.09-131.00 143.00   82
 10  \w    103.00 178.00   1.00   24.00    --  107.09  77.00 -90.00   75
 11  \w     34.00 133.00   1.00   24.00    --  107.09 -45.00 -90.00   99
 12  \w     79.00 178.00   1.00   24.00    --  107.09  30.00  60.00   99
 13  \w     34.00 133.00   1.00   24.00    --  107.09 -45.00-180.00   99
 14  \w     24.00 107.00   1.00   24.00    --  107.09 -94.00-180.00   83
 15  \w   -115.00 -13.00   1.00    6.00    --  -41.59 -57.00-150.00  102
 16  \w   -115.00 -13.00   1.00    6.00    --  -41.59 -57.00 -60.00  102
 17  \w   -115.00 -13.00   1.00    6.00    --  -41.59 -57.00 120.00  102
 18  \w   -115.00 -13.00   1.00    6.00    --  -41.59 -57.00  60.00  102
 19  \w     78.00 178.00   1.00   24.00    --  107.09  61.00-120.00  100
 20  \w     78.00 178.00   1.00   24.00    --  107.09  61.00 -30.00  100
 21  \w     81.00 178.00   1.00   24.00    --  107.09  45.00 120.00   97
 22  \w     78.00 178.00   1.00   24.00    --  107.09  61.00 150.00  100
 23  \w     54.00 178.00   1.00   24.00    --  107.09  15.00-120.00  124
 24  \w     78.00 178.00   1.00   24.00    --  107.09  61.00   0.00  100
 25  \w     78.00 178.00   1.00   24.00    --  107.09  61.00  60.00  100
 26  \w     78.00 178.00   1.00   24.00    --  107.09  61.00 -90.00  100
 27  \w    -87.00  -6.00   1.00    6.00    --  -41.59 125.00 -30.00   81
 28  \w   -115.00 -13.00   1.00    6.00    --  -41.59 -57.00 150.00  102
 29  \w   -115.00 -13.00   1.00    6.00    --  -41.59 -57.00 -90.00  102
 30  \w   -115.00 -13.00   1.00    6.00    --  -41.59 -57.00   0.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0385572000
_diffrn_orient_matrix_UB_12      0.0324368000
_diffrn_orient_matrix_UB_13      0.0846335000
_diffrn_orient_matrix_UB_21      0.0374650000
_diffrn_orient_matrix_UB_22      0.1250838000
_diffrn_orient_matrix_UB_23      -0.0014680000
_diffrn_orient_matrix_UB_31      -0.1210294000
_diffrn_orient_matrix_UB_32      -0.0180987000
_diffrn_orient_matrix_UB_33      0.0021498000
_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  0.1067
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            48255
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.796
_diffrn_reflns_theta_min         2.428
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    18.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
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    1.633
_exptl_crystal_description       plate
_exptl_crystal_F_000             1404
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.057
_refine_diff_density_max         3.934
_refine_diff_density_min         -1.952
_refine_diff_density_rms         0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     785
_refine_ls_number_reflns         11564
_refine_ls_number_restraints     897
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2102
_refine_ls_wR_factor_ref         0.2250
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9715
_reflns_number_total             11564
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02381k2.cif
_cod_data_source_block           tbu-ibox-x2
_cod_depositor_comments          'Adding full bibliography for 7158495.cif.'
_cod_original_cell_volume        2957.28(17)
_cod_database_code               7158495
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C46 H34 N14 O4 Cl6 I4'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1A-Cl1 = C1A-Cl2 = C1A-Cl3 = C1AA-Cl1A = C1AA-Cl2A = C1AA-Cl3A
 1.75 with sigma of 0.02
 Cl1-Cl2 \\sim Cl1-Cl3 \\sim Cl1A-Cl2A \\sim Cl1A-Cl3A \\sim Cl2A-Cl3A \\sim
Cl2-Cl3
 with sigma of 0.01
 C12-C14 \\sim C12-C14A
 with sigma of 0.04
 C12-C13 \\sim C12-C13A
 with sigma of 0.02
 C12-C17 \\sim C12-C17A
 with sigma of 0.02
 C13-C15 \\sim C13A-C15
 with sigma of 0.04
 C13-C14 \\sim C13A-C14A
 with sigma of 0.02
 C12-C16 \\sim C12-C16A
 with sigma of 0.04
 C14-C15 \\sim C14A-C15
 with sigma of 0.02
 C15-C17 \\sim C15-C17A
 with sigma of 0.04
 C15-C16 \\sim C15-C16A
 with sigma of 0.02
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 O4-C28 \\sim O4A-C28
 with sigma of 0.04
 O4-C41 \\sim O4A-C41A
 with sigma of 0.02
 O4-C43 \\sim O4A-C43A
 with sigma of 0.04
 O3-C40 \\sim O3A-C40A
 with sigma of 0.02
 C41-C42 \\sim C41A-C42A
 with sigma of 0.02
 C28-C40 \\sim C28-C40A
 with sigma of 0.02
 C41-C43 \\sim C41A-C43A
 with sigma of 0.02
 O4-C42 \\sim O4A-C42A
 with sigma of 0.04
 O4-C44 \\sim O4A-C44A
 with sigma of 0.04
 C42-C43 \\sim C42A-C43A
 with sigma of 0.04
 C40-C41 \\sim C40A-C41A
 with sigma of 0.04
 C41-C44 \\sim C41A-C44A
 with sigma of 0.02
 C42-C44 \\sim C42A-C44A
 with sigma of 0.04
 C43-C44 \\sim C43A-C44A
 with sigma of 0.04
 O3-O4 \\sim O3A-O4A
 with sigma of 0.04
 O4-C40 \\sim O4A-C40A
 with sigma of 0.02
 O3-C28 \\sim O3A-C28
 with sigma of 0.04
 C36-C37 \\sim C36A-C37
 with sigma of 0.02
 C37-C39 \\sim C37-C39A
 with sigma of 0.04
 C38-C39 \\sim C38A-C39A
 with sigma of 0.02
 C37-C38 \\sim C37-C38A
 with sigma of 0.02
 C34-C35 \\sim C34-C35A
 with sigma of 0.02
 C34-C36 \\sim C34-C36A
 with sigma of 0.04
 C34-C39 \\sim C34-C39A
 with sigma of 0.02
 C34-C38 \\sim C34-C38A
 with sigma of 0.04
 C35-C37 \\sim C35A-C37
 with sigma of 0.04
 C35-C36 \\sim C35A-C36A
 with sigma of 0.02
3. Restrained planarity
 C36A, C35A, C34, C39A, C38A, C37
 with sigma of 0.02
 C38, C37, C36, C35, C34, C39
 with sigma of 0.02
 C28, C40A, O3A, O4A
 with sigma of 0.02
 C28, C40, O3, O4
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C14A \\sim C14 \\sim C13 \\sim C13A \\sim C17A \\sim C17 \\sim C16 \\sim C16A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C38 \\sim C38A \\sim C39 \\sim C39A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
O4 \\sim O4A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
C40 \\sim C40A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
O3 \\sim O3A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
Uanis(O3A) \\sim Ueq, Uanis(O3) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C1AA) = Uanis(C1A)
Uanis(C41) = Uanis(C41A)
Uanis(C40A) = Uanis(C40)
Uanis(O4) = Uanis(O4A)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=Sof(C1AA)=Sof(H1AB)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C1A)=Sof(H1AA)=FVAR(1)
 Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=
 Sof(H17A)=1-FVAR(2)
 Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=FVAR(2)
 Sof(O3A)=Sof(C40A)=Sof(O4A)=Sof(C41A)=Sof(C43A)=Sof(H43D)=Sof(H43E)=Sof(H43F)=
 Sof(C44A)=Sof(H44D)=Sof(H44E)=Sof(H44F)=Sof(C42A)=Sof(H42D)=Sof(H42E)=
 Sof(H42F)=1-FVAR(3)
 Sof(O3)=Sof(O4)=Sof(C40)=Sof(C41)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(H42C)=
 Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(H43C)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=
 FVAR(3)
 Sof(C38A)=Sof(H38A)=Sof(C39A)=Sof(H39A)=Sof(C35A)=Sof(H35A)=Sof(C36A)=
 Sof(H36A)=1-FVAR(4)
 Sof(C35)=Sof(H35)=Sof(C36)=Sof(H36)=Sof(C38)=Sof(H38)=Sof(C39)=Sof(H39)=FVAR(4)
7.a Ternary CH refined with riding coordinates:
 C1A(H1AA), C1AA(H1AB)
7.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C23(H23A,H23B), C33(H33A,H33B)
7.c Me refined with riding coordinates:
 C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C43A(H43D,H43E,
 H43F), C44A(H44D,H44E,H44F), C42A(H42D,H42E,H42F)
7.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C13(H13), C14(H14), C16(H16), C17(H17), C27(H27), C29(H29),
 C35(H35), C36(H36), C38(H38), C39(H39), C13A(H13A), C14A(H14A), C16A(H16A),
 C17A(H17A), C38A(H38A), C39A(H39A), C35A(H35A), C36A(H36A)
7.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              60017
_shelx_fab_checksum              53759
_olex2_date_sample_data_collection 2021-05-06
_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 2.222
_oxdiff_exptl_absorpt_empirical_full_min 0.430