The synthesis of a pyridine-N-oxide isophthalamide rotaxane utilizing supplementary amide hydrogen bond interactions.
Evans, Nicholas H.; Gell, Charles E.; Peach, Michael J. G.; Organic & biomolecular chemistry 14 (2016) 7972–7981; doi:10.1039/c6ob01435f

data_7155225
_publ_section_title
;
 The synthesis of a pyridine-N-oxide isophthalamide rotaxane utilizing
 supplementary amide hydrogen bond interactions.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7972
_journal_page_last               7981
_journal_paper_doi               10.1039/c6ob01435f
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C32 H30 N2 O4'
_chemical_formula_sum            'C32 H30 N2 O4'
_chemical_formula_weight         506.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-04-11 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.314(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7998(4)
_cell_length_b                   13.3320(6)
_cell_length_c                   12.0001(6)
_cell_measurement_reflns_used    2255
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      73.4030
_cell_measurement_theta_min      3.9210
_cell_volume                     1320.28(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2303
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w    -59.00  33.00   1.00   40.00    --  -38.50  38.00 150.00   92
  2  \w   -116.00  -5.00   1.00   40.00    --  -38.50 -19.00 -30.00  111
  3  \w     25.00 109.00   1.00  200.00    --  104.55 -94.00  90.00   84
  4  \w    124.00 165.00   1.00  200.00    --  104.55 125.00 -60.00   41
  5  \w     84.00 171.00   1.00  200.00    --  104.55  45.00-120.00   87
  6  \w     57.00 125.00   1.00  200.00    --  104.55 -30.00-180.00   68
  7  \w     75.00 171.00   1.00  200.00    --  104.55  77.00 -30.00   96
  8  \w     76.00 117.00   1.00  200.00    --  104.55-125.00  60.00   41
  9  \w    -47.00  29.00   1.00   40.00    --  -38.50  38.00 -30.00   76
 10  \w     33.00  59.00   1.00   40.00    --   42.26-125.00-180.00   26
 11  \w      3.00  78.00   1.00   40.00    --   42.26 -99.00 -90.00   75
 12  \w     25.00 108.00   1.00  200.00    --  104.55 -94.00-120.00   83
 13  \w    153.00 178.00   1.00  200.00    --  104.55  15.00  60.00   25
 14  \w     35.00  63.00   1.00  200.00    --  104.55 -94.00 150.00   28
 15  \w     90.00 116.00   1.00  200.00    --  104.55 -45.00 -60.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1057548000
_diffrn_orient_matrix_UB_12      -0.0824488000
_diffrn_orient_matrix_UB_13      -0.0798343000
_diffrn_orient_matrix_UB_21      0.0247810000
_diffrn_orient_matrix_UB_22      0.0479522000
_diffrn_orient_matrix_UB_23      -0.1092435000
_diffrn_orient_matrix_UB_31      0.1517998000
_diffrn_orient_matrix_UB_32      -0.0652997000
_diffrn_orient_matrix_UB_33      0.0206974000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7970
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.902
_diffrn_reflns_theta_min         3.928
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.274
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.066
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1372 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4647
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0431P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.814
_reflns_Friedel_fraction_max     0.750
_reflns_number_gt                3926
_reflns_number_total             4647
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01435f5.cif
_cod_data_source_block           ne104
_cod_depositor_comments
'Adding full bibliography for 7155225--7155226.cif.'
_cod_database_code               7155225
_chemical_oxdiff_formula         'C20 H30 N2 O2'
_chemical_oxdiff_usercomment     ne118
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C9(H9A,H9B), C7(H7A,H7B), C16(H16A,H16B), C20(H20A,H20B), C22(H22A,H22B),
 C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 N30(H30), N17(H17), C2(H2), C34(H34), C12(H12), C38(H38), C6(H6), C11(H11),
 C15(H15), C14(H14), C35(H35), C24(H24), C27(H27), C3(H3), C36(H36), C4(H4),
 C28(H28), C25(H25)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder 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 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.831