[3]Foldarotaxane-Mediated Synthesis of an Improbable [2]Rotaxane
Koehler, Victor; Gauthier, Maxime; Yao, Chenhao; Fournel-Marotte, Karine; Waeles, Philip; Kauffmann, Brice; Huc, Ivan; Coutrot, Frédéric; Ferrand, Yann; Chemical Communications  (2022) –; doi:10.1039/D2CC03066G

data_7130310
_publ_section_title
;
 [3]Foldarotaxane-Mediated Synthesis of an Improbable [2]Rotaxane
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03066G
_journal_year                    2022
_chemical_formula_moiety         'C239 H224 F13 N39 O36, C28 H35 N3 O6'
_chemical_formula_sum            'C267 H259 F13 N42 O42'
_chemical_formula_weight         4975.15
_chemical_name_systematic        634
_chemical_properties_physical    Air-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-13
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-05-27 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   28.3005(4)
_cell_length_b                   47.5333(10)
_cell_length_c                   51.9586(7)
_cell_measurement_reflns_used    24600
_cell_measurement_temperature    135
_cell_measurement_theta_max      48.7830
_cell_measurement_theta_min      1.9970
_cell_volume                     69896(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      135
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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    -65.00 -34.00   1.00   30.00    --  -64.90  30.00 144.00   31
  2  \w   -120.00 -85.00   1.00   30.00    --  -64.90  30.00 144.00   35
  3  \w    -87.00 -21.00   1.00    1.00    --    0.00  28.00 -60.00   66
  4  \w    -15.00  46.00   1.00    1.00    --    0.00  28.00 -60.00   61
  5  \w    -19.00   6.00   1.00    1.00    --    5.00  30.00 144.00   25
  6  \w   -153.00-116.00   1.00   30.00    --  -64.90  46.00 -60.00   37
  7  \w   -154.00 -53.00   1.00   30.00    --  -64.90  28.00 -60.00  101
  8  \w   -144.00-118.00   1.00   30.00    --  -64.90  18.00 -90.00   26
  9  \w    -85.00  24.00   1.00   30.00    --  -64.90  46.00 -60.00  109
 10  \w    -82.00 -56.00   1.00   30.00    --  -64.90  18.00 -90.00   26
 11  \w    -31.00  -6.00   1.00   30.00    --  -64.90  30.00 144.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0515340000
_diffrn_orient_matrix_UB_12      -0.0046879000
_diffrn_orient_matrix_UB_13      -0.0085718000
_diffrn_orient_matrix_UB_21      0.0140736000
_diffrn_orient_matrix_UB_22      -0.0284417000
_diffrn_orient_matrix_UB_23      -0.0119703000
_diffrn_orient_matrix_UB_31      -0.0106364000
_diffrn_orient_matrix_UB_32      -0.0148304000
_diffrn_orient_matrix_UB_33      0.0257079000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            160074
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        51.380
_diffrn_reflns_theta_max         51.380
_diffrn_reflns_theta_min         2.006
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    0.946
_exptl_crystal_description       block
_exptl_crystal_F_000             20864
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     3320
_refine_ls_number_reflns         37609
_refine_ls_number_restraints     198
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0953
_refine_ls_shift/su_max          3.297
_refine_ls_shift/su_mean         0.024
_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          0.2948
_refine_ls_wR_factor_ref         0.3297
_reflns_Friedel_coverage         0.000
_reflns_number_gt                21419
_reflns_number_total             37609
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03066g2.cif
_cod_data_source_block           634
_cod_database_code               7130310
_publcif_datablock.id            {8b75e194-ef77-459c-be9c-78e0c002087f}
_shelx_shelxl_version_number     2018/3
_cell_oxdiff_angle_alpha         89.9632(16)
_cell_oxdiff_angle_beta          89.9940(14)
_cell_oxdiff_angle_gamma         89.9692(18)
_cell_oxdiff_length_a            28.2829(6)
_cell_oxdiff_length_b            47.5236(12)
_cell_oxdiff_length_c            52.0015(8)
_cell_oxdiff_measurement_reflns_used 24600
_cell_oxdiff_volume              69896(2)
_olex2_refinement_description
;
1. 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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C338-C320
 1.54 with sigma of 0.02
 C330-C2
 1.54 with sigma of 0.02
 C306-C30
 1.54 with sigma of 0.002
 C24-C21
 1.54 with sigma of 0.02
 C47-C2AA = C3-C2AA = C9-C2AA
 1.54 with sigma of 0.02
 C6-C2
 2.8 with sigma of 0.02
 C330-C2 = C6-C330 = C330-C304
 1.54 with sigma of 0.002
 C24-C21 = C3AA-C24 = C318-C24
 1.54 with sigma of 0.02
 C1_1-C2_1 \\sim C2_1-C3_1 \\sim C3_1-C4_1 \\sim C4_1-C5_1 \\sim C5_1-C6_1
\\sim C6_1-C1_1
 with sigma of 0.02
 C1_1-C5_1 \\sim C1_1-C5_1 \\sim C4_1-C2_1 \\sim C4_1-C6_1 \\sim C6_1-C2_1
\\sim C5_1-C3_1
 with sigma of 0.04
3. Restrained planarity
 C1_1, C2_1, C3_1, C4_1, C5_1, C6_1
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C1_1 \\sim C2_1 \\sim C3_1 \\sim C4_1 \\sim C5_1 \\sim C6_1: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C1_1, C2_1, C3_1, C4_1, C5_1, C6_1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C30, C306, C337, C295
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C39, C328, C49, C269
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C21, C24, C3AA, C318, O217
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C9, C2AA, C3, C47, O309
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C21, C3AA, C318, O217
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: H15D(0.5) H15E(0.5) H15F(0.5) H15G(0.5) H23A(0.5) H23B(0.5)
 H23C(0.5) H23D(0.5) C4(0.5) H4(0.5) C5(0.5) H5(0.5)
7.a Ternary CH refined with riding coordinates:
 C268(H268), C284(H284), C286(H286), C293(H293), C306(H306), C307(H307),
 C312(H312), C314(H314), C320(H320), C328(H328), C330(H330), C332(H332),
 C24(H24), C12(H12), C2AA(H2AA), C4(H4), C5(H5)
7.b Secondary CH2 refined with riding coordinates:
 C074(H07A,H07B), C084(H08A,H08B), C110(H11A,H11B), C114(H11C,H11D), C117(H11E,
 H11F), C142(H14A,H14B), C157(H15D,H15E), C157(H15F,H15G), C161(H16A,H16B),
 C187(H18A,H18B), C204(H20A,H20B), C220(H22A,H22B), C225(H22F,H22G), C235(H23A,
 H23B), C235(H23C,H23D), C241(H24A,H24B), C254(H25A,H25B), C262(H26A,H26B),
 C264(H26C,H26D), C267(H26E,H26F), C269(H26G,H26H), C295(H29A,H29B), C302(H30A,
 H30B), C304(H30C,H30D), C316(H31D,H31E), C318(H31I,H31J), C20(H20C,H20D),
 C47(H47A,H47B)
7.c Aromatic/amide H refined with riding coordinates:
 N027(H027), N028(H028), N035(H035), N036(H036), N040(H040), N048(H048),
 N051(H051), C058(H058), C063(H063), N066(H066), N071(H071), N076(H076),
 C081(H081), N083(H083), N086(H086), N087(H087), N088(H088), N095(H095),
 C109(H109), N115(H115), N116(H116), N119(H119), C122(H122), N124(H124),
 C130(H130), N138(H138), C144(H144), C145(H145), N150(H150), C152(H152),
 C153(H153), C156(H156), C159(H159), C163(H163), C165(H165), C166(H166),
 C170(H170), C172(H172), C174(H174), C175(H175), C178(H178), C182(H182),
 C184(H184), C190(H190), C194(H194), C197(H197), C198(H198), C199(H199),
 C200(H200), C202(H202), C208(H208), C215(H215), C216(H216), C218(H218),
 C221(H221), C222(H222), C223(H223), C226(H226), C227(H227), C230(H230),
 C231(H231), C236(H236), C246(H246), C250(H250), C251(H251), C255(H255),
 C256(H256), C263(H263), C266(H266), C271(H271), C275(H275), C279(H279),
 C280(H280), C281(H281), C282(H282), C288(H288), C289(H289), C290(H290),
 C292(H292), C294(H294), C296(H296), C301(H301), C313(H313), C315(H315), C1(H1),
  C2(H2), C3(H3), C4(H4), C5(H5)
7.d Idealised Me refined as rotating group:
 C229(H22C,H22D,H22E), C297(H29C,H29D,H29E), C305(H30E,H30F,H30G), C311(H31A,
 H31B,H31C), C317(H31F,H31G,H31H), C322(H32A,H32B,H32C), C323(H32D,H32E,H32F),
 C324(H32G,H32H,H32I), C325(H32J,H32K,H32L), C326(H32M,H32N,H32O), C329(H32P,
 H32Q,H32R), C331(H33A,H33B,H33C), C334(H33D,H33E,H33F), C335(H33G,H33H,H33I),
 C337(H33J,H33K,H33L), C338(H33M,H33N,H33O), C339(H33P,H33Q,H33R), C15(H15A,
 H15B,H15C), C44(H44A,H44B,H44C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C30(H30H,
 H30I,H30J), C0AA(H0AA,H0AB,H0AC), C49(H49A,H49B,H49C), C3AA(H3AA,H3AB,H3AC),
 C1AA(H1AA,H1AB,H1AC), C50(H50A,H50B,H50C), C39(H39A,H39B,H39C), C4AA(H4AA,H4AB,
 H4AC), C35(H35A,H35B,H35C), C2(H2A,H2B,H2C), C21(H21A,H21B,H21C), C9(H9A,H9B,
 H9C), C3(H3A,H3B,H3C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              44326
_shelx_hkl_checksum              48617
_shelx_fab_checksum              64869
_olex2_submission_original_sample_id vk634
_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 1.729
_oxdiff_exptl_absorpt_empirical_full_min 0.563
_publcif_funding_html
;
;