An amide hydrogen bond templated [1]rotaxane displaying a peptide motif - demonstrating an expedient route to synthetic mimics of lasso peptides.
Young, Matthew J.; Akien, Geoffrey R.; Evans, Nicholas H.; Organic & biomolecular chemistry 18 (2020) 5203–5209; doi:10.1039/d0ob01190h

data_7157554
_publ_section_title
;
 An amide hydrogen bond templated [1]rotaxane displaying a peptide motif -
 demonstrating an expedient route to synthetic mimics of lasso peptides.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5203
_journal_page_last               5209
_journal_paper_doi               10.1039/d0ob01190h
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C28 H31 N3 O5, C H4 O'
_chemical_formula_sum            'C29 H35 N3 O6'
_chemical_formula_weight         521.60
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-04-06 deposited with the CCDC.	2020-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.176(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9726(2)
_cell_length_b                   30.0112(8)
_cell_length_c                   11.2602(3)
_cell_measurement_reflns_used    6998
_cell_measurement_temperature    99.96(11)
_cell_measurement_theta_max      71.8890
_cell_measurement_theta_min      3.9740
_cell_volume                     2651.82(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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_environment      N~2~
_diffrn_ambient_temperature      99.96(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2303
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_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    -62.00 -27.00   1.00    9.84    --  -41.22  38.00  90.00   35
  2  \w    -88.00  -3.00   1.00    9.84    --  -41.22 125.00  90.00   85
  3  \w   -113.00 -18.00   1.00    9.84    --  -41.22 -57.00 -60.00   95
  4  \w    135.00 169.00   1.00   39.35    --  102.76  61.00  90.00   34
  5  \w     88.00 176.00   1.00   39.35    --  102.76  30.00-120.00   88
  6  \w     30.00 117.00   1.00   39.35    --  102.76-125.00  60.00   87
  7  \w     55.00 117.00   1.00   39.35    --  102.76-125.00-120.00   62
  8  \w    112.00 176.00   1.00   39.35    --  102.76 125.00-120.00   64
  9  \w    116.00 174.00   1.00   39.35    --  102.76 125.00  60.00   58
 10  \w    124.00 156.00   1.00   39.35    --  102.76 125.00-150.00   32
 11  \w     89.00 165.00   1.00   39.35    --  102.76  77.00 -30.00   76
;
_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      0.0493953000
_diffrn_orient_matrix_UB_12      -0.0055958000
_diffrn_orient_matrix_UB_13      0.1377735000
_diffrn_orient_matrix_UB_21      -0.0012445000
_diffrn_orient_matrix_UB_22      -0.0510077000
_diffrn_orient_matrix_UB_23      -0.0154819000
_diffrn_orient_matrix_UB_31      0.1899543000
_diffrn_orient_matrix_UB_32      0.0011527000
_diffrn_orient_matrix_UB_33      -0.0105774000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11400
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.099
_diffrn_reflns_theta_min         3.989
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.306
_exptl_crystal_description       prism
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     709
_refine_ls_number_reflns         7672
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0639
_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^)+(0.1157P)^2^+1.7488P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1809
_refine_ls_wR_factor_ref         0.1835
_reflns_Friedel_coverage         0.961
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                7163
_reflns_number_total             7672
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01190h2.cif
_cod_data_source_block           mc256
_cod_depositor_comments          'Adding full bibliography for 7157554.cif.'
_cod_database_code               7157554
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         C28H30N3O5
_chemical_oxdiff_usercomment     'Nick E amino macrocyle'
_diffrn_oxdiff_digest_frames
;
0158a108fe08afca8a02618fff34d3970c00025e2aa
;
_diffrn_oxdiff_digest_hkl
;
01027fc33e596a6e21c01fadada615066a094e
;
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5(3)
 0.5(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 O6A-H6A = O6-H6
 0.8 with sigma of 0.02
 O3A-C17A \\sim O3A-C16A \\sim O5_$1-C20_$1 \\sim O5B_$1-C20_$1 \\sim
O5B_$1-C21_$1 \\sim O5_$1-
 C21_$1
 with sigma of 0.02
4. Others
 Sof(H20C)=Sof(H20D)=Sof(H21C)=Sof(H21D)=Sof(O5B)=1-FVAR(1)
 Sof(O5)=Sof(H20A)=Sof(H20B)=Sof(H21A)=Sof(H21B)=FVAR(1)
5.a Rotating group:
 N2(H2A,H2B), N2A(H2AA)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
 C20(H20A,H20B), C20(H20C,H20D), C21(H21A,H21B), C21(H21C,H21D), C28(H28A,H28B),
  C9A(H9AA,H9AB), C16A(H16C,H16D), C17A(H17C,H17D), C18A(H18C,H18D), C19A(H19C,
 H19D), C20A(H20E,H20F), C21A(H21E,H21F), C28A(H28C,H28D)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C3(H3A), C5(H5), C7(H7), C11(H11), C12(H12), C14(H14),
 C15(H15), C0AA(H0AA), C24(H24), C26(H26), C27(H27), N1A(H1A), N3A(H3AA),
 C3A(H3AB), C5A(H5A), C7A(H7A), C11A(H11A), C12A(H12A), C14A(H14A), C15A(H15A),
 C23A(H23A), C24A(H24A), C26A(H26A), C27A(H27A)
5.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C29A(H29D,H29E,H29F)
5.e Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_shelx_res_checksum              67415
_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 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.667