A pyridine-<i>N</i>-oxide catenane for cation recognition.
Barlow, Sean R.; Halcovitch, Nathan R.; Evans, Nicholas H.; Organic & biomolecular chemistry 22 (2024) 3001–3008; doi:10.1039/d4ob00176a

data_7159855
_publ_section_title
;
 A pyridine-<i>N</i>-oxide catenane for cation recognition.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3001
_journal_page_last               3008
_journal_paper_doi               10.1039/d4ob00176a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C31 H29 N3 O5, [+ solvents]'
_chemical_formula_sum            'C31 H29 N3 O5'
_chemical_formula_weight         523.57
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-11-02 deposited with the CCDC.	2024-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                102.718(2)
_cell_angle_beta                 111.425(3)
_cell_angle_gamma                105.578(3)
_cell_formula_units_Z            4
_cell_length_a                   14.6339(5)
_cell_length_b                   15.1689(5)
_cell_length_c                   16.0492(3)
_cell_measurement_reflns_used    12442
_cell_measurement_temperature    139.9(4)
_cell_measurement_theta_max      75.5180
_cell_measurement_theta_min      4.6080
_cell_volume                     2986.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      139.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_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    -66.00  33.00   1.00   10.00    --  -41.73  38.00-180.00   99
  2  \w    -70.00  31.00   1.00   10.00    --  -41.73  57.00  30.00  101
  3  \w   -114.00 -14.00   1.00   10.00    --  -41.73 -57.00-120.00  100
  4  \w      8.00  42.00   1.00   10.00    --   41.73  81.00 125.27   34
  5  \w      6.00  82.00   1.00   10.00    --   41.73 -99.00  60.00   76
  6  \w     10.00  36.00   1.00   10.00    --   41.73  73.00-111.21   26
  7  \w      8.00  42.00   1.00   10.00    --   41.73  81.00-171.02   34
  8  \w     83.00 178.00   1.00   40.00    --  112.00  61.00-150.00   95
  9  \w     82.00 178.00   1.00   40.00    --  112.00  68.00 -84.15   96
 10  \w     36.00 145.00   1.00   40.00    --  112.00 -77.00 150.00  109
 11  \w     83.00 178.00   1.00   40.00    --  112.00  61.00 150.00   95
 12  \w     83.00 178.00   1.00   40.00    --  112.00  61.00 120.00   95
 13  \w     29.00 107.00   1.00   40.00    --  112.00 -94.00-120.00   78
 14  \w     39.00 109.00   1.00   40.00    --  112.00-111.00   0.00   70
 15  \w     40.00 141.00   1.00   40.00    --  112.00 -61.00 -30.00  101
 16  \w     84.00 178.00   1.00   40.00    --  112.00  30.00-150.00   94
 17  \w     84.00 178.00   1.00   40.00    --  112.00  30.00 -90.00   94
 18  \w     39.00 109.00   1.00   40.00    --  112.00-111.00 -60.00   70
 19  \w     39.00 109.00   1.00   40.00    --  112.00-111.00  60.00   70
 20  \w     29.00 107.00   1.00   40.00    --  112.00 -94.00 120.00   78
 21  \w     39.00 109.00   1.00   40.00    --  112.00-111.00-150.00   70
 22  \w     39.00 109.00   1.00   40.00    --  112.00-111.00-120.00   70
 23  \w     39.00 138.00   1.00   40.00    --  112.00 -45.00-120.00   99
 24  \w     39.00 109.00   1.00   40.00    --  112.00-111.00 -30.00   70
 25  \w    104.00 178.00   1.00   40.00    --  112.00 111.00-150.00   74
 26  \w    104.00 178.00   1.00   40.00    --  112.00 111.00 -30.00   74
 27  \w     36.00 140.00   1.00   40.00    --  112.00 -30.00 -90.00  104
 28  \w     40.00 126.00   1.00   40.00    --  112.00-142.00-147.28   86
 29  \w     39.00 109.00   1.00   40.00    --  112.00-111.00  30.00   70
 30  \w     39.00 109.00   1.00   40.00    --  112.00-111.00  90.00   70
 31  \w     34.00 108.00   1.00   40.00    --  112.00-104.00  98.20   74
 32  \w   -116.00 -17.00   1.00   10.00    --  -41.73 -38.00  30.00   99
 33  \w    -87.00  -6.00   1.00   10.00    --  -41.73 125.00-180.00   81
 34  \w      9.00  42.00   1.00   10.00    --   41.73  80.00  16.77   33
;
_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      -0.0335461000
_diffrn_orient_matrix_UB_12      0.0700575000
_diffrn_orient_matrix_UB_13      0.0564864000
_diffrn_orient_matrix_UB_21      0.0937540000
_diffrn_orient_matrix_UB_22      0.0879877000
_diffrn_orient_matrix_UB_23      0.0140037000
_diffrn_orient_matrix_UB_31      -0.0713444000
_diffrn_orient_matrix_UB_32      0.0082701000
_diffrn_orient_matrix_UB_33      -0.0936931000
_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  0.0811
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48309
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.266
_diffrn_reflns_theta_min         3.510
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0007(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   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     712
_refine_ls_number_reflns         12420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0658
_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^)+(0.1073P)^2^+0.1992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.2141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8456
_reflns_number_total             12420
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00176a2.cif
_cod_data_source_block           ne129_auto
_cod_depositor_comments
'Adding full bibliography for 7159855--7159856.cif.'
_cod_original_cell_volume        2986.62(17)
_cod_database_code               7159855
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C56  H56  N56  O56 '
_chemical_oxdiff_usercomment     SB137
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.950
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C14(H14A,H14B), C23(H23A,H23B), C30(H30A,H30B),
 C31(H31A,H31B), C6A(H6AA,H6AB), C7A(H7AA,H7AB), C14A(H14C,H14D), C23A(H23C,
 H23D), C30A(H30C,H30D), C31A(H31C,H31D)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2A), C3(H3A), C4(H4), C9(H9), C10(H10), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C21(H21), C25(H25), C26(H26), C28(H28), C29(H29),
  N2A(H2AA), C2A(H2AB), C3A(H3AB), C4A(H4A), C9A(H9A), C10A(H10A), C12A(H12A),
 C13A(H13A), C17A(H17A), C18A(H18A), C19A(H19A), C21A(H21A), C25A(H25A),
 C26A(H26A), C28A(H28A), C29A(H29A)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 174 electrons were 
found in a volume of 569 A^3 per unit cell. 
This is consistent with the presence of 
3 molecules of CHCl3 per Unit Cell 
which account for 174 electrons.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              57390
_shelx_hkl_checksum              1978
_shelx_fab_checksum              93623
_olex2_exptl_crystal_mounting_method
'mounted on a Mitegen loop using Paratone-N oil'
_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 2.341
_oxdiff_exptl_absorpt_empirical_full_min 0.465