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_7159856
_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 O4'
_chemical_formula_sum            'C31 H29 N3 O4'
_chemical_formula_weight         507.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-19
_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                90
_cell_angle_beta                 99.4400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.5269(2)
_cell_length_b                   11.10560(10)
_cell_length_c                   21.8729(2)
_cell_measurement_reflns_used    16060
_cell_measurement_temperature    99.93(16)
_cell_measurement_theta_max      74.0320
_cell_measurement_theta_min      4.0720
_cell_volume                     5158.32(8)
_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      99.93(16)
_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   -109.00 -14.00   1.00   12.50    --  -41.73 -57.00 -60.00   95
  2  \w    -61.00  31.00   1.00   12.50    --  -41.73  57.00  90.00   92
  3  \w    -64.00  30.00   1.00   12.50    --  -41.73  40.00-120.00   94
  4  \w    -87.00 -56.00   1.00   12.50    --  -41.73 125.00 150.00   31
  5  \w     37.00 109.00   1.00   50.00    --  107.28-111.00   0.00   72
  6  \w     53.00 127.00   1.00   50.00    --  107.28 -45.00 -60.00   74
  7  \w    105.00 178.00   1.00   50.00    --  107.28  30.00 150.00   73
  8  \w    117.00 178.00   1.00   50.00    --  107.28  77.00  30.00   61
  9  \w     39.00 132.00   1.00   50.00    --  107.28 -45.00  60.00   93
 10  \w     67.00 109.00   1.00   50.00    --  107.28-111.00-180.00   42
 11  \w     80.00 175.00   1.00   50.00    --  107.28  61.00  90.00   95
 12  \w    106.00 176.00   1.00   50.00    --  107.28  77.00   0.00   70
 13  \w     55.00 106.00   1.00   50.00    --  107.28 -94.00  60.00   51
 14  \w     43.00 138.00   1.00   50.00    --  107.28 -77.00-180.00   95
;
_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      0.0186512000
_diffrn_orient_matrix_UB_12      -0.1185850000
_diffrn_orient_matrix_UB_13      0.0347091000
_diffrn_orient_matrix_UB_21      0.0683352000
_diffrn_orient_matrix_UB_22      0.0162430000
_diffrn_orient_matrix_UB_23      -0.0110503000
_diffrn_orient_matrix_UB_31      0.0156935000
_diffrn_orient_matrix_UB_32      0.0700970000
_diffrn_orient_matrix_UB_33      0.0614297000
_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  0.0224
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32736
_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         74.347
_diffrn_reflns_theta_min         4.098
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95005
_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    1.307
_exptl_crystal_description       prism
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     701
_refine_ls_number_reflns         10318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0427P)^2^+1.5631P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8944
_reflns_number_total             10318
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00176a2.cif
_cod_data_source_block           ne143_auto
_cod_depositor_comments
'Adding full bibliography for 7159855--7159856.cif.'
_cod_database_code               7159856
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     SB133
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.939
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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:
 C2(H2A), C3(H3A), C4(H4), C9(H9), C10(H10), C12(H12), C13(H13), C17(H17),
 C19(H19), C20(H20), C21(H21), C25(H25), C26(H26), C28(H28), C29(H29),
 C2A(H2AB), C3A(H3AB), C4A(H4A), C9A(H9A), C10A(H10A), C12A(H12A), C13A(H13A),
 C17A(H17A), C19A(H19A), C20A(H20A), C21A(H21A), C25A(H25A), C26A(H26A),
 C28A(H28A), C29A(H29A)
;
_shelx_res_checksum              76492
_shelx_hkl_checksum              33361
_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 2.682
_oxdiff_exptl_absorpt_empirical_full_min 0.808