Spontaneous Assembly of Rotaxanes from a Primary Amine, Crown Ether and Electrophile.
Fielden, Stephen D. P.; Leigh, David A.; McTernan, Charlie T.; Pérez-Saavedra, Borja; Vitorica-Yrezabal, Iñigo J; Journal of the American Chemical Society 140 (2018) 6049–6052; doi:10.1021/jacs.8b03394

data_4132372
_publ_section_title
;
 Spontaneous Assembly of Rotaxanes from a Primary Amine, Crown Ether and
 Electrophile.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6049
_journal_page_last               6052
_journal_paper_doi               10.1021/jacs.8b03394
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'Cl, C16 H32 O8, C30 H48 N, 2(H2 O)'
_chemical_formula_sum            'C46 H84 Cl N O10'
_chemical_formula_weight         846.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.5755(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.22760(14)
_cell_length_b                   16.08441(15)
_cell_length_c                   20.7588(2)
_cell_measurement_reflns_used    25614
_cell_measurement_temperature    150
_cell_measurement_theta_max      71.9370
_cell_measurement_theta_min      2.2490
_cell_volume                     4873.11(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.977
_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     31.00  56.00   1.00    1.00    --   55.00  25.00  80.00   25
  2  \w     95.00 170.00   1.00    1.00    --  110.00  25.00  80.00   75
  3  \w     31.00  58.00   1.00    1.00    --  110.00  25.00  80.00   27
  4  \w    -85.00  78.00   1.00    1.00    --    0.00  57.00 150.00  163
  5  \w    -12.00  14.00   1.00    1.00    --    0.00  60.00-180.00   26
  6  \w     -3.00  24.00   1.00    1.00    --    0.00  25.00  80.00   27
  7  \w    -34.00   5.00   1.00    1.00    --   55.00  60.00 150.00   39
  8  \w    -31.00 142.00   1.00    1.00    --   55.00  60.00-180.00  173
  9  \w    -15.00 143.00   1.00    1.00    --   55.00  57.00 -60.00  158
 10  \w     31.00 141.00   1.00    1.00    --   55.00  60.00 150.00  110
 11  \w    -28.00 108.00   1.00    1.00    --   55.00  43.00 -90.00  136
 12  \w    -30.00  91.00   1.00    1.00    --   55.00  57.00-150.00  121
 13  \w     62.00  89.00   1.00    1.00    --  110.00  60.00 150.00   27
 14  \w     21.00  47.00   1.00    1.00    --  110.00  60.00-180.00   26
 15  \w    138.00 180.00   1.00    1.00    --  110.00  60.00 120.00   42
 16  \w     81.00 198.00   1.00    1.00    --  110.00  60.00-180.00  117
 17  \w     85.00 111.00   1.00    1.00    --  110.00  46.00 120.00   26
 18  \w     21.00  48.00   1.00    1.00    --  110.00  60.00 150.00   27
 19  \w    107.00 132.00   1.00    1.00    --  110.00  46.00-150.00   25
 20  \w     22.00  49.00   1.00    1.00    --  110.00  60.00 120.00   27
 21  \w     21.00  47.00   1.00    1.00    --  110.00  46.00-180.00   26
 22  \w     21.00  47.00   1.00    1.00    --  110.00  57.00-120.00   26
 23  \w     21.00  47.00   1.00    1.00    --  110.00  57.00-150.00   26
 24  \w     21.00  47.00   1.00    1.00    --  110.00  60.00-120.00   26
 25  \w    107.00 141.00   1.00    1.00    --  110.00  60.00-120.00   34
 26  \w    145.00 197.00   1.00    1.00    --  110.00  60.00-120.00   52
 27  \w     21.00  47.00   1.00    1.00    --  110.00  57.00 150.00   26
 28  \w     21.00  47.00   1.00    1.00    --  110.00  46.00 150.00   26
 29  \w     22.00  49.00   1.00    1.00    --  110.00  60.00-150.00   27
 30  \w     21.00  47.00   1.00    1.00    --  110.00  34.00-150.00   26
 31  \w     22.00  47.00   1.00    1.00    --  110.00  46.00 120.00   25
 32  \w     21.00 119.00   1.00    1.00    --  110.00  11.00 120.00   98
 33  \w    118.00 179.00   1.00    1.00    --  110.00  46.00 120.00   61
 34  \w    109.00 190.00   1.00    1.00    --  110.00  23.00-120.00   81
 35  \w     21.00  57.00   1.00    1.00    --  110.00  34.00-120.00   36
 36  \w     21.00  48.00   1.00    1.00    --  110.00  34.00-180.00   27
 37  \w    107.00 133.00   1.00    1.00    --  110.00  46.00-120.00   26
 38  \w    112.00 199.00   1.00    1.00    --  110.00  11.00-150.00   87
 39  \w     22.00  47.00   1.00    1.00    --  110.00  34.00 120.00   25
 40  \w     21.00  47.00   1.00    1.00    --  110.00  34.00 150.00   26
 41  \w     21.00  39.00   1.00    1.00    --  110.00  57.00-180.00   18
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0181614000
_diffrn_orient_matrix_UB_12      -0.0398233000
_diffrn_orient_matrix_UB_13      -0.0624897000
_diffrn_orient_matrix_UB_21      -0.1027419000
_diffrn_orient_matrix_UB_22      0.0062367000
_diffrn_orient_matrix_UB_23      -0.0377001000
_diffrn_orient_matrix_UB_31      0.0158207000
_diffrn_orient_matrix_UB_32      0.0868965000
_diffrn_orient_matrix_UB_33      -0.0258851000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            44061
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.109
_diffrn_reflns_theta_min         3.534
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         9392
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0908P)^2^+2.9413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1521
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9084
_reflns_number_total             9392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b03394_si_002.cif
_cod_data_source_block           ldl3
_cod_original_cell_volume        4873.10(8)
_cod_database_code               4132372
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.615
_shelx_estimated_absorpt_t_min   0.578
_reflns_odcompleteness_completeness 98.61
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O58-H58B = O58-H58A = O57-H57B = O57-H57A
 0.85 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 N33(H33A,H33B), C34(H34A,H34B), C32(H32A,H32B), C4(H4A,H4B), C13(H13A,H13B),
 C22(H22A,H22B), C3(H3A,H3B), C25(H25A,H25B), C21(H21A,H21B), C16(H16A,H16B),
 C6(H6A,H6B), C19(H19A,H19B), C10(H10A,H10B), C12(H12A,H12B), C7(H7A,H7B),
 C15(H15A,H15B), C9(H9A,H9B), C24(H24A,H24B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C29(H29), C31(H31), C27(H27), C36(H36), C38(H38), C40(H40)
3.c Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C50(H50A,H50B,H50C), C46(H46A,H46B,H46C), C47(H47A,H47B,
 H47C), C43(H43A,H43B,H43C), C51(H51A,H51B,H51C), C54(H54A,H54B,H54C), C44(H44A,
 H44B,H44C), C55(H55A,H55B,H55C), C48(H48A,H48B,H48C), C56(H56A,H56B,H56C),
 C52(H52A,H52B,H52C)
;
_shelx_res_checksum              47223
_shelx_hkl_checksum              88369
_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 1.542
_oxdiff_exptl_absorpt_empirical_full_min 0.641