Rapid synthesis of hydrogen bond templated handcuff rotaxanes.
Barlow, Sean R.; Tomkinson, David; Halcovitch, Nathan R.; Evans, Nicholas H.; Organic & biomolecular chemistry 22 (2024) 5393–5400; doi:10.1039/d4ob00672k

data_7159971
_publ_section_title
;
 Rapid synthesis of hydrogen bond templated handcuff rotaxanes.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5393
_journal_page_last               5400
_journal_paper_doi               10.1039/d4ob00672k
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C74 H80 N6 O11'
_chemical_formula_sum            'C74 H80 N6 O11'
_chemical_formula_weight         1229.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-03-25 deposited with the CCDC.	2024-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.854(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   27.7031(18)
_cell_length_b                   13.0253(10)
_cell_length_c                   9.5007(5)
_cell_measurement_reflns_used    4785
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.8920
_cell_measurement_theta_min      4.7910
_cell_volume                     3420.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_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    -66.00  33.00   1.00   25.00    --  -41.68  37.00-120.00   99
  2  \w    -66.00  33.00   1.00   25.00    --  -41.68  37.00  90.00   99
  3  \w     27.00  96.00   1.00   25.00    --   41.68-125.00-180.00   69
  4  \w     27.00  96.00   1.00   25.00    --   41.68-125.00-150.00   69
  5  \w     76.00 178.00   1.00  100.00    --  104.41  30.00-150.00  102
  6  \w     31.00 109.00   1.00  100.00    --  104.41-111.00  90.00   78
  7  \w     39.00 130.00   1.00  100.00    --  104.41-149.00  33.00   91
  8  \w    104.00 178.00   1.00  100.00    --  104.41 111.00   0.00   74
  9  \w    104.00 178.00   1.00  100.00    --  104.41 111.00  60.00   74
 10  \w     31.00 130.00   1.00  100.00    --  104.41 -45.00 -90.00   99
 11  \w     31.00 130.00   1.00  100.00    --  104.41 -45.00  30.00   99
 12  \w   -116.00 -17.00   1.00   25.00    --  -41.68 -37.00  90.00   99
 13  \w   -115.00 -14.00   1.00   25.00    --  -41.68 -57.00  30.00  101
 14  \w   -115.00 -14.00   1.00   25.00    --  -41.68 -57.00 -60.00  101
;
_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      -0.0300674000
_diffrn_orient_matrix_UB_12      0.0984746000
_diffrn_orient_matrix_UB_13      0.0144463000
_diffrn_orient_matrix_UB_21      -0.0466786000
_diffrn_orient_matrix_UB_22      -0.0607262000
_diffrn_orient_matrix_UB_23      -0.0396906000
_diffrn_orient_matrix_UB_31      -0.0051729000
_diffrn_orient_matrix_UB_32      -0.0245538000
_diffrn_orient_matrix_UB_33      0.1568855000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8629
_diffrn_reflns_point_group_measured_fraction_full 0.527
_diffrn_reflns_point_group_measured_fraction_max 0.515
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.840
_diffrn_reflns_theta_min         3.751
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (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    1.194
_exptl_crystal_description       plate
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.142
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     828
_refine_ls_number_reflns         8629
_refine_ls_number_restraints     187
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.1052
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3054
_refine_ls_wR_factor_ref         0.3275
_reflns_Friedel_coverage         0.052
_reflns_Friedel_fraction_full    0.055
_reflns_Friedel_fraction_max     0.051
_reflns_number_gt                6135
_reflns_number_total             8629
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9952\% 
around [1.00 0.00 0.00] (reciprocal) or [0.98 -0.00 0.19] (direct)
;
_cod_data_source_file            d4ob00672k2.cif
_cod_data_source_block           ne157_twin1_hklf4
_cod_depositor_comments          'Adding full bibliography for 7159971.cif.'
_cod_database_code               7159971
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     SB159-2
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.549(3)
 0.451(3)
2. 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
3. Restrained distances
 O6-C40 \\sim O02L-C37 \\sim O1-C36 \\sim O1-C1
 with sigma of 0.02
 O6-C39 \\sim O6-C76 \\sim O6-C40 \\sim O02L-C38 \\sim O02L-C75
 with sigma of 0.02
 C36-C37 \\sim C02H-C37
 with sigma of 0.02
 C37-C02H \\sim C8A-C02H
 with sigma of 0.02
 O1-C36 \\sim O1-C02H
 with sigma of 0.02
 C36-C37 \\sim C36-C8A
 with sigma of 0.02
 O02L-C37 \\sim O02L-C8A
 with sigma of 0.02
 C8A-C02H \\sim C37-C36
 with sigma of 0.02
 O4-C22 \\sim O4-C23 \\sim O3-C16 \\sim O3-C15
 with sigma of 0.02
 C16-C17 \\sim C22-C21
 with sigma of 0.02
 O9-C55 \\sim O9-C54 \\sim O8-C61 \\sim O8-C62
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C41) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C8A)
\\sim Ueq, Uanis(C02H) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C36) \\sim Ueq,
Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C31) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C15) \\sim Ueq: with
sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C12) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C8) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C4) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(C02H) = Uanis(C39)
Uanis(C37) = Uanis(C75)
Uanis(C36) = Uanis(C76)
Uanis(C8A) = Uanis(C38)
Uanis(C36) = Uanis(C37)
Uanis(C02H) = Uanis(C8A)
5. Others
 Sof(C02H)=Sof(H02A)=Sof(H02B)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C75)=Sof(H75A)=
 Sof(H75B)=Sof(C76)=Sof(H76A)=Sof(H76B)=1-FVAR(1)
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(C38)=Sof(H38A)=
 Sof(H38B)=Sof(C39)=Sof(H39A)=Sof(H39B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C15(H15A,H15B), C16(H16A,H16B), C22(H22A,H22B), C23(H23A,H23B),
 C30(H30A,H30B), C47(H47A,H47B), C54(H54A,H54B), C55(H55A,H55B), C61(H61A,H61B),
  C62(H62A,H62B), C69(H69A,H69B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,
 H38B), C39(H39A,H39B), C02H(H02A,H02B), C8A(H8AA,H8AB), C75(H75A,H75B),
 C76(H76A,H76B)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N4(H4), N5(H5), C2(H2A), C4(H4A), C6(H6), C10(H10), C11(H11),
 C13(H13), C14(H14), C18(H18), C20(H20), C25(H25), C26(H26), C28(H28), C29(H29),
  C41(H41), C43(H43), C45(H45), C49(H49), C50(H50), C52(H52), C53(H53),
 C57(H57), C59(H59), C64(H64), C65(H65), C67(H67), C68(H68)
6.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C72(H72A,H72B,
 H72C), C73(H73A,H73B,H73C), C74(H74A,H74B,H74C)
;
_shelx_res_checksum              99599
_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 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.778
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2