Single-Step Enantioselective Synthesis of Mechanically Planar Chiral [2]Rotaxanes Using a Chiral Leaving Group Strategy.
Tian, Chong; Fielden, Stephen D. P.; Pérez-Saavedra, Borja; Vitorica-Yrezabal, Iñigo J; Leigh, David A.; Journal of the American Chemical Society 142 (2020) 9803–9808; doi:10.1021/jacs.0c03447

data_4134955
_publ_section_title
;
 Single-Step Enantioselective Synthesis of Mechanically Planar Chiral
 [2]Rotaxanes Using a Chiral Leaving Group Strategy.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9803
_journal_page_last               9808
_journal_paper_doi               10.1021/jacs.0c03447
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C28 H33 N O10, C24 H27 F6 N O, 2(C3 H8 O)'
_chemical_formula_sum            'C58 H76 F6 N2 O13'
_chemical_formula_weight         1123.20
_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     direct
_audit_creation_date             2019-11-28
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                74.834(3)
_cell_angle_beta                 76.745(2)
_cell_angle_gamma                81.664(2)
_cell_formula_units_Z            2
_cell_length_a                   13.2744(3)
_cell_length_b                   14.5586(4)
_cell_length_c                   16.0139(5)
_cell_measurement_reflns_used    29877
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      75.7620
_cell_measurement_theta_min      2.8860
_cell_volume                     2895.51(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_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    'ShelXS n/a (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.948
_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    -34.00  54.00   1.00    2.00    --    5.00  38.00  30.00   88
  2  \w    -35.00  93.00   1.00    2.00    --    5.00  76.00-180.00  128
  3  \w    -94.00 -55.00   1.00    2.00    --  -45.90 -76.00   0.00   39
  4  \w    -31.00  -6.00   1.00    2.00    --  -45.90 -76.00   0.00   25
  5  \w    -85.00  42.00   1.00    2.00    --  -45.90  76.00  90.00  127
  6  \w    -40.00  -6.00   1.00    2.00    --  -45.90 -76.00 120.00   34
  7  \w   -130.00 -97.00   1.00    2.00    --  -45.90 -76.00   0.00   33
  8  \w   -134.00 -50.00   1.00    2.00    --  -45.90 -76.00 120.00   84
  9  \w   -150.00-123.00   1.00    2.00    --  -62.00 -76.00 111.21   27
 10  \w    -58.00 -22.00   1.00    2.00    --  -62.00 -76.00 -69.02   36
 11  \w   -137.00-110.00   1.00    2.00    --  -62.00 -76.00 -69.02   27
 12  \w    -53.00 -22.00   1.00    2.00    --  -62.00 -76.00 111.21   31
 13  \w    -61.00 -26.00   1.00    2.00    --  -66.00 -76.00 -18.34   35
 14  \w   -145.00-119.00   1.00    2.00    --  -66.00 -76.00   9.50   26
 15  \w    -56.00 -26.00   1.00    2.00    --  -66.00 -76.00-130.77   30
 16  \w   -154.00-128.00   1.00    2.00    --  -66.00 -76.00-130.77   26
 17  \w    -60.00 -27.00   1.00    2.00    --  -66.00 -75.00 -86.34   33
 18  \w    -52.00 -26.00   1.00    2.00    --  -66.00 -76.00   9.50   26
 19  \w    -59.00 -34.00   1.00    2.00    --  -74.00 -76.00-172.03   25
 20  \w   -120.00 -95.00   1.00    2.00    --  -74.00 -76.00-172.03   25
 21  \w   -160.00-135.00   1.00    2.00    --  -74.00 -75.00  94.85   25
 22  \w    -60.00 -35.00   1.00    2.00    --  -74.00 -75.00  94.85   25
 23  \w    -61.00 -34.00   1.00    2.00    --  -74.00 -76.00 -41.03   27
 24  \w   -164.00-139.00   1.00    7.00    --  -78.00 -74.00 164.81   25
 25  \w    -64.00 -39.00   1.00    7.00    --  -78.00 -74.00 164.81   25
 26  \w    -72.00 -43.00   1.00    7.00    --  -82.00 -74.00 137.51   29
 27  \w    -70.00 -43.00   1.00    7.00    --  -82.00 -74.00  42.58   27
 28  \w   -169.00-142.00   1.00    7.00    --  -82.00 -76.00  77.09   27
 29  \w    -68.00 -42.00   1.00    7.00    --  -82.00 -76.00  77.09   26
 30  \w    -73.00 -47.00   1.00    7.00    --  -86.00 -74.00 104.05   26
 31  \w    -74.00 -47.00   1.00    7.00    --  -86.00 -75.00-112.41   27
 32  \w    -77.00 -51.00   1.00    7.00    --  -90.00 -75.00 -73.12   26
 33  \w   -101.00 -55.00   1.00    7.00    --  -94.00 -75.00-124.08   46
 34  \w   -178.00-107.00   1.00    7.00    --  -94.00 -75.00-124.08   71
 35  \w   -113.00 -59.00   1.00    7.00    --  -94.00 -67.00  90.94   54
 36  \w   -182.00-120.00   1.00    7.00    --  -94.00 -67.00  90.94   62
 37  \w   -107.00 -55.00   1.00    7.00    --  -94.00 -75.00  17.44   52
 38  \w   -180.00-108.00   1.00    7.00    --  -94.00 -75.00  17.44   72
 39  \w   -162.00 -57.00   1.00    7.00    --  -94.00 -70.00  26.06  105
 40  \w    -98.00 -55.00   1.00    7.00    --  -94.00 -75.00 -31.72   43
 41  \w   -183.00-109.00   1.00    7.00    --  -94.00 -75.00 -31.72   74
 42  \w   -151.00 -55.00   1.00    7.00    --  -94.00 -75.00 -51.14   96
 43  \w    -85.00 -58.00   1.00    7.00    --  -98.00 -76.00 151.70   27
 44  \w   -184.00 -89.00   1.00    7.00    --  -98.00 -76.00 151.70   95
 45  \w   -165.00 -60.00   1.00    7.00    --  -98.00 -73.00  83.46  105
 46  \w   -176.00 -64.00   1.00    7.00    --  -98.00 -73.00-162.66  112
 47  \w   -185.00 -60.00   1.00    7.00    --  -98.00 -72.00-176.71  125
 48  \w    -90.00 -60.00   1.00    7.00    --  -98.00 -72.00 -80.87   30
 49  \w   -141.00 -59.00   1.00    7.00    --  -98.00 -75.00-142.40   82
 50  \w   -184.00 -94.00   1.00    7.00    --  -98.00 -72.00 -80.87   90
 51  \w   -191.00 -64.00   1.00    7.00    -- -102.00 -73.00  63.28  127
 52  \w   -170.00 -64.00   1.00    7.00    -- -102.00 -72.00  -7.77  106
 53  \w   -102.00 -51.00   1.00    7.00    -- -107.20  76.00  90.00   51
 54  \w   -148.00 -20.00   1.00    7.00    -- -107.20  76.00 120.00  128
 55  \w   -112.00 -52.00   1.00    7.00    -- -107.20  76.00 -30.00   60
 56  \w   -137.00 -68.00   1.00    7.00    -- -107.20  76.00 -90.00   69
 57  \w   -194.00 -68.00   1.00    7.00    -- -107.20 -74.00 133.42  126
 58  \w   -196.00 -67.00   1.00    7.00    -- -107.20 -76.00 -90.00  129
 59  \w   -115.00 -40.00   1.00    7.00    -- -107.20  76.00-150.00   75
 60  \w   -119.00 -51.00   1.00    7.00    -- -107.20  76.00  30.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1184301000
_diffrn_orient_matrix_UB_12      -0.0021997000
_diffrn_orient_matrix_UB_13      -0.0343808000
_diffrn_orient_matrix_UB_21      -0.0162101000
_diffrn_orient_matrix_UB_22      0.0122089000
_diffrn_orient_matrix_UB_23      -0.0946608000
_diffrn_orient_matrix_UB_31      -0.0067101000
_diffrn_orient_matrix_UB_32      0.1093867000
_diffrn_orient_matrix_UB_33      -0.0144058000
_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  0.0379
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            71520
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.200
_diffrn_reflns_theta_min         2.918
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
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    1.288
_exptl_crystal_description       plank
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00108(10)
_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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     765
_refine_ls_number_reflns         11495
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0457P)^2^+1.7920P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10183
_reflns_number_total             11495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c03447_si_002.cif
_cod_data_source_block           rdl43
_cod_depositor_comments          'Adding full bibliography for 4134955.cif.'
_cod_database_code               4134955
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.874
_reflns_odcompleteness_completeness 99.31
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O76-C77 \\sim O76A-C77A
 with sigma of 0.02
 C77-C79 \\sim C77A-C79A
 with sigma of 0.02
 C77-C78 \\sim C77A-C78A
 with sigma of 0.02
 O76-C79 \\sim O76A-C79A
 with sigma of 0.04
 O76-C78 \\sim O76A-C78A
 with sigma of 0.04
 C79-C78 \\sim C79A-C78A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C78A \\sim O76 \\sim C77 \\sim C79 \\sim C78 \\sim C77A \\sim O76A \\sim C79A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(C77A)=Sof(H77A)=Sof(C78A)=Sof(H78D)=Sof(H78E)=Sof(H78F)=Sof(C79A)=
 Sof(H79D)=Sof(H79E)=Sof(H79F)=Sof(O76A)=Sof(H76A)=1-FVAR(1)
 Sof(O76)=Sof(H76)=Sof(C77)=Sof(H77)=Sof(C79)=Sof(H79A)=Sof(H79B)=Sof(H79C)=
 Sof(C78)=Sof(H78A)=Sof(H78B)=Sof(H78C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C73(H73), C77(H77), C77A(H77A)
5.b Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C28(H28A,H28B), C17(H17A,H17B), C12(H12A,H12B), C18(H18A,
 H18B), C5(H5A,H5B), C15(H15A,H15B), C27(H27A,H27B), C6(H6A,H6B), C14(H14A,
 H14B), C8(H8A,H8B), C11(H11A,H11B), C9(H9A,H9B)
5.c Aromatic/amide H refined with riding coordinates:
 N47(H47), C61(H61), C41(H41), C21(H21), C59(H59), C43(H43), C63(H63),
 C45(H45), C2(H2), C31(H31), C35(H35), C22(H22), C33(H33), C36(H36), C24(H24),
 C34(H34)
5.d Idealised Me refined as rotating group:
 C66(H66A,H66B,H66C), C65(H65A,H65B,H65C), C69(H69A,H69B,H69C), C67(H67A,H67B,
 H67C), C70(H70A,H70B,H70C), C71(H71A,H71B,H71C), C75(H75A,H75B,H75C), C74(H74A,
 H74B,H74C), C79(H79A,H79B,H79C), C78(H78A,H78B,H78C), C78A(H78D,H78E,H78F),
 C79A(H79D,H79E,H79F)
5.e Idealised tetrahedral OH refined as rotating group:
 O72(H72), O76(H76), O76A(H76A)
;
_shelx_res_checksum              68581
_shelx_hkl_checksum              81747
_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.824