Neutral Isocyanide-Templated Assembly of Pillar[5]arene [2] and [3]Pseudorotaxanes
Khamphaijun, Korawit; Namnouad, Phitawat; Docker, Andrew; Ruengsuk, Araya; Tantirungrotechai, Jonggol; Díaz-Torres, Raúl; Harding, David J.; Bunchuay, Thanthapatra; Chemical Communications  (2022) –; doi:10.1039/D2CC02255A

data_7130171
_publ_section_title
;
 Neutral Isocyanide-Templated Assembly of Pillar[5]arene [2] and
 [3]Pseudorotaxanes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02255A
_journal_year                    2022
_chemical_formula_moiety         '2(C55 H70 O10), C12 H20 N2, 2[H2O]'
_chemical_formula_sum            'C122 H164 N2 O22'
_chemical_formula_weight         2010.54
_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
_audit_creation_date             2022-02-16
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-04-18 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                89.0960(10)
_cell_angle_beta                 86.1870(10)
_cell_angle_gamma                83.0700(10)
_cell_formula_units_Z            1
_cell_length_a                   13.02310(10)
_cell_length_b                   14.51270(10)
_cell_length_c                   15.24250(10)
_cell_measurement_reflns_used    35242
_cell_measurement_temperature    149.9(2)
_cell_measurement_theta_max      68.3440
_cell_measurement_theta_min      2.8930
_cell_volume                     2853.37(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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     -9.00  78.00   0.50    0.40    --   40.91-106.00 -88.00  174
  2  \w     29.00 107.00   0.50    1.60    --   96.59-106.00 -88.00  156
  3  \w     83.00 157.00   0.50    1.60    --   96.59 106.00  11.00  148
  4  \w   -109.00 -32.00   0.50    0.40    --  -40.91 -25.00 -60.00  154
  5  \w    -53.00  23.00   0.50    0.40    --  -40.91  37.00 -90.00  152
  6  \w   -104.00 -25.00   0.50    0.40    --  -40.91 -50.00-120.00  158
  7  \w   -109.00 -32.00   0.50    0.40    --  -40.91 -25.00-150.00  154
  8  \w   -104.00 -25.00   0.50    0.40    --  -40.91 -50.00  30.00  158
  9  \w   -105.00 -19.00   0.50    0.40    --  -40.91 -69.00 145.73  172
 10  \w    -57.00  22.00   0.50    0.40    --  -40.91  50.00-180.00  158
 11  \w   -105.00 -29.00   0.50    0.40    --  -40.91 -37.00  60.00  152
 12  \w    -97.00 -14.00   0.50    0.40    --  -40.91 138.00  90.00  166
 13  \w    -78.00   9.00   0.50    0.40    --  -40.91 106.00  11.00  174
 14  \w     15.00  42.00   0.50    0.40    --   40.91  81.00  69.45   54
 15  \w     15.00  42.00   0.50    0.40    --   40.91  82.00 -65.17   54
 16  \w    -13.00  77.00   0.50    0.40    --   40.91-104.00 -30.00  180
 17  \w     15.00  42.00   0.50    0.40    --   40.91  82.00 177.69   54
 18  \w     15.00  42.00   0.50    0.40    --   40.91  82.00  82.14   54
 19  \w     16.00  42.00   0.50    0.40    --   40.91  78.00 -46.87   52
 20  \w     16.00  42.00   0.50    0.40    --   40.91  78.00-127.73   52
 21  \w     15.00  42.00   0.50    0.40    --   40.91  82.00  20.98   54
 22  \w     29.00 105.00   0.50    0.40    --   40.91  37.00 -90.00  152
 23  \w     29.00 105.00   0.50    0.40    --   40.91  37.00   0.00  152
 24  \w     15.00  42.00   0.50    0.40    --   40.91  82.00 -19.33   54
 25  \w     33.00 126.00   0.50    1.60    --   96.59-144.00  60.00  186
 26  \w     88.00 157.00   0.50    1.60    --   96.59  25.00 -90.00  138
 27  \w     33.00 126.00   0.50    1.60    --   96.59-144.00  90.00  186
 28  \w     27.00 105.00   0.50    1.60    --   96.59 -96.00  60.00  156
 29  \w     32.00 109.00   0.50    1.60    --   96.59-117.00  60.00  154
 30  \w     34.00 110.00   0.50    1.60    --   96.59 -42.00 150.00  152
 31  \w     31.00 106.00   0.50    1.60    --   96.59 -33.00-120.00  150
 32  \w     29.00 105.00   0.50    1.60    --   96.59 -25.00 150.00  152
 33  \w     84.00 157.00   0.50    1.60    --   96.59  96.00 -30.00  146
 34  \w     34.00 110.00   0.50    1.60    --   96.59 -42.00  30.00  152
 35  \w     83.00 157.00   0.50    1.60    --   96.59  17.00  30.00  148
 36  \w     87.00 157.00   0.50    1.60    --   96.59  33.00-180.00  140
 37  \w     88.00 157.00   0.50    1.60    --   96.59  25.00 150.00  138
 38  \w     32.00 109.00   0.50    1.60    --   96.59-117.00 150.00  154
 39  \w     88.00 157.00   0.50    1.60    --   96.59  25.00 -60.00  138
 40  \w     31.00 124.00   0.50    1.60    --   96.59 -86.00-150.00  186
 41  \w     32.00 109.00   0.50    1.60    --   96.59-117.00-150.00  154
 42  \w     32.00 109.00   0.50    1.60    --   96.59-117.00-120.00  154
 43  \w     26.00 110.00   0.50    1.60    --   96.59 -17.00-150.00  168
 44  \w     34.00 113.00   0.50    1.60    --   96.59 -50.00 120.00  158
 45  \w     33.00 118.00   0.50    1.60    --   96.59 -68.00  60.00  170
 46  \w     26.00 110.00   0.50    1.60    --   96.59 -17.00 -30.00  168
 47  \w     34.00 113.00   0.50    1.60    --   96.59 -50.00 -30.00  158
 48  \w     33.00 126.00   0.50    1.60    --   96.59-144.00-150.00  186
 49  \w     33.00 115.00   0.50    1.60    --   96.59 -59.00-120.00  164
 50  \w     32.00 109.00   0.50    1.60    --   96.59-117.00   0.00  154
 51  \w   -105.00 -18.00   0.50    0.40    --  -40.91 -71.00  69.75  174
 52  \w    -50.00  27.00   0.50    0.40    --  -40.91  25.00-180.00  154
 53  \w    -66.00  24.00   0.50    0.40    --  -40.91  77.00 -60.00  180
 54  \w    -63.00  32.00   0.50    0.40    --  -40.91  12.00 -60.00  190
 55  \w   -104.00 -25.00   0.50    0.40    --  -40.91 -50.00-180.00  158
 56  \w   -105.00 -18.00   0.50    0.40    --  -40.91 -72.00  29.52  174
 57  \w   -105.00 -20.00   0.50    0.40    --  -40.91 -66.00 -38.71  170
 58  \w   -104.00 -21.00   0.50    0.40    --  -40.91 -63.00-150.00  166
 59  \w     15.00  42.00   0.50    0.40    --   40.91  82.00 162.04   54
 60  \w     16.00  42.00   0.50    0.40    --   40.91  79.00-159.71   52
 61  \w     15.00  42.00   0.50    0.40    --   40.91  82.00  12.48   54
 62  \w     15.00  42.00   0.50    0.40    --   40.91  81.00 130.55   54
 63  \w     16.00  42.00   0.50    0.40    --   40.91  78.00 -76.84   52
 64  \w     15.00  42.00   0.50    0.40    --   40.91  82.00 -77.19   54
 65  \w     15.00  42.00   0.50    0.40    --   40.91  77.00 158.19   54
 66  \w    -22.00  57.00   0.50    0.40    --   40.91 -50.00 -30.00  158
 67  \w     15.00  42.00   0.50    0.40    --   40.91  81.00 -33.24   54
 68  \w     29.00 105.00   0.50    0.40    --   40.91  37.00-180.00  152
 69  \w     21.00 105.00   0.50    0.40    --   40.91  63.00 120.00  168
 70  \w     15.00  42.00   0.50    0.40    --   40.91  82.00-114.95   54
 71  \w     16.00  42.00   0.50    0.40    --   40.91  76.00  46.86   52
 72  \w     16.00  42.00   0.50    0.40    --   40.91  80.00-109.07   52
 73  \w     16.00  42.00   0.50    0.40    --   40.91  78.00-146.72   52
 74  \w    -23.00  53.00   0.50    0.40    --   40.91 -37.00  60.00  152
 75  \w     74.00 157.00   0.50    1.60    --   96.59  71.00  95.33  166
 76  \w     75.00 157.00   0.50    1.60    --   96.59  68.00  30.00  164
 77  \w     78.00 157.00   0.50    1.60    --   96.59  59.00-150.00  158
 78  \w     77.00 157.00   0.50    1.60    --   96.59  62.00 -42.33  160
 79  \w     84.00 157.00   0.50    1.60    --   96.59  42.00  90.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0718924000
_diffrn_orient_matrix_UB_12      0.0039129000
_diffrn_orient_matrix_UB_13      -0.0765948000
_diffrn_orient_matrix_UB_21      -0.0843115000
_diffrn_orient_matrix_UB_22      -0.0379534000
_diffrn_orient_matrix_UB_23      0.0612259000
_diffrn_orient_matrix_UB_31      -0.0445404000
_diffrn_orient_matrix_UB_32      0.0998990000
_diffrn_orient_matrix_UB_33      0.0254117000
_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  0.0440
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            57277
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.588
_diffrn_reflns_theta_min         2.906
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.170
_exptl_crystal_description       block
_exptl_crystal_F_000             1086
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.128
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     659
_refine_ls_number_reflns         10461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.5184P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1150
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9031
_reflns_number_total             10461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02255a2.cif
_cod_data_source_block           etp5a-c10dinc-dcm-meoh-150k
_cod_database_code               7130171
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C67H90O10N2
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.818
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C18(H18A,H18B), C20(H20A,H20B),
 C22(H22A,H22B), C29(H29A,H29B), C31(H31A,H31B), C33(H33A,H33B), C40(H40A,H40B),
  C42(H42A,H42B), C44(H44A,H44B), C51(H51A,H51B), C53(H53A,H53B), C55(H55A,
 H55B), C56(H56A,H56B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B),
 C60(H60A,H60B)
1.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C14(H14), C17(H17), C25(H25), C28(H28), C36(H36), C39(H39),
 C47(H47), C50(H50)
1.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C41(H41A,H41B,H41C), C43(H43A,
 H43B,H43C), C52(H52A,H52B,H52C), C54(H54A,H54B,H54C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              20435
_shelx_fab_checksum              68639
_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 1.573
_oxdiff_exptl_absorpt_empirical_full_min 0.678