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_7130167
_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         'C55 H70 O10, C6 H8 N2'
_chemical_formula_sum            'C61 H78 N2 O10'
_chemical_formula_weight         999.25
_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     dual
_audit_creation_date             2022-02-15
_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                102.061(2)
_cell_angle_beta                 90.230(3)
_cell_angle_gamma                92.195(2)
_cell_formula_units_Z            4
_cell_length_a                   13.2049(4)
_cell_length_b                   20.9781(5)
_cell_length_c                   21.1995(6)
_cell_measurement_reflns_used    18433
_cell_measurement_temperature    152(3)
_cell_measurement_theta_max      67.8780
_cell_measurement_theta_min      2.0860
_cell_volume                     5738.3(3)
_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      152(3)
_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 0.975
_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     26.00 104.00   0.50    2.00    --   40.91  47.00 -11.00  156
  2  \w    -22.00  56.00   0.50    2.00    --   40.91 -47.00-160.00  156
  3  \w     82.00 157.00   0.50    8.00    --   96.59  47.00 -11.00  150
  4  \w     34.00 111.00   0.50    8.00    --   96.59 -47.00-160.00  154
  5  \w   -104.00 -21.00   0.50    2.00    --  -40.91 -63.00-150.00  166
  6  \w    -50.00  27.00   0.50    2.00    --  -40.91  25.00  30.00  154
  7  \w   -103.00 -26.00   0.50    2.00    --  -40.91 -47.00-160.00  154
  8  \w    -77.00  14.00   0.50    2.00    --  -40.91 104.00  60.00  182
  9  \w   -104.00 -21.00   0.50    2.00    --  -40.91 -63.00  30.00  166
 10  \w    -55.00  22.00   0.50    2.00    --  -40.91  47.00 -11.00  154
 11  \w     16.00  42.00   0.50    2.00    --   40.91  80.00  80.20   52
 12  \w     16.00  42.00   0.50    2.00    --   40.91  76.00 -13.05   52
 13  \w     29.00 105.00   0.50    2.00    --   40.91  37.00 -60.00  152
 14  \w    -23.00  53.00   0.50    2.00    --   40.91 -37.00  60.00  152
 15  \w     15.00  42.00   0.50    2.00    --   40.91  81.00  33.62   54
 16  \w     14.00  97.00   0.50    2.00    --   40.91-138.00 -30.00  166
 17  \w     16.00  42.00   0.50    2.00    --   40.91  79.00 152.41   52
 18  \w     15.00  42.00   0.50    2.00    --   40.91  81.00-114.74   54
 19  \w     16.00  42.00   0.50    2.00    --   40.91  76.00-168.68   52
 20  \w     16.00  42.00   0.50    2.00    --   40.91  76.00 -72.65   52
 21  \w     16.00  42.00   0.50    2.00    --   40.91  80.00  44.67   52
 22  \w     25.00 104.00   0.50    2.00    --   40.91  50.00 150.00  158
 23  \w     15.00  42.00   0.50    2.00    --   40.91  82.00 177.57   54
 24  \w     25.00 104.00   0.50    2.00    --   40.91  50.00  90.00  158
 25  \w     14.00  97.00   0.50    2.00    --   40.91-138.00 -60.00  166
 26  \w     83.00 157.00   0.50    8.00    --   96.59  77.00-120.00  148
 27  \w     33.00 126.00   0.50    8.00    --   96.59-144.00 120.00  186
 28  \w     88.00 157.00   0.50    8.00    --   96.59  25.00  30.00  138
 29  \w     27.00 105.00   0.50    8.00    --   96.59 -96.00  30.00  156
 30  \w     33.00 126.00   0.50    8.00    --   96.59-144.00  60.00  186
 31  \w     83.00 157.00   0.50    8.00    --   96.59  77.00 -60.00  148
 32  \w     32.00 109.00   0.50    8.00    --   96.59-117.00 120.00  154
 33  \w     88.00 157.00   0.50    8.00    --   96.59  25.00 120.00  138
 34  \w     33.00 126.00   0.50    8.00    --   96.59-144.00 -60.00  186
 35  \w     33.00 126.00   0.50    8.00    --   96.59-144.00-120.00  186
 36  \w     27.00 105.00   0.50    8.00    --   96.59 -96.00-150.00  156
 37  \w     33.00 115.00   0.50    8.00    --   96.59 -59.00  30.00  164
 38  \w     83.00 157.00   0.50    8.00    --   96.59  77.00 -90.00  148
 39  \w     88.00 157.00   0.50    8.00    --   96.59  25.00 -60.00  138
 40  \w     73.00 157.00   0.50    8.00    --   96.59  73.00-143.31  168
 41  \w     32.00 122.00   0.50    8.00    --   96.59 -77.00-120.00  180
 42  \w     83.00 157.00   0.50    8.00    --   96.59  17.00  90.00  148
 43  \w     81.00 157.00   0.50    8.00    --   96.59 117.00 -30.00  152
 44  \w     67.00 157.00   0.50    8.00    --   96.59 144.00 -90.00  180
 45  \w     33.00 126.00   0.50    8.00    --   96.59-144.00  30.00  186
 46  \w     32.00 109.00   0.50    8.00    --   96.59-117.00 -90.00  154
 47  \w     31.00 106.00   0.50    8.00    --   96.59 -33.00   0.00  150
 48  \w     33.00 115.00   0.50    8.00    --   96.59 -59.00 120.00  164
 49  \w     67.00 157.00   0.50    8.00    --   96.59 144.00-120.00  180
 50  \w     88.00 157.00   0.50    8.00    --   96.59  25.00-180.00  138
 51  \w     31.00 124.00   0.50    8.00    --   96.59 -86.00  60.00  186
 52  \w     32.00 122.00   0.50    8.00    --   96.59 -77.00 -60.00  180
 53  \w     34.00 110.00   0.50    8.00    --   96.59 -42.00-120.00  152
 54  \w     84.00 157.00   0.50    8.00    --   96.59  96.00-120.00  146
 55  \w     84.00 157.00   0.50    8.00    --   96.59  96.00-180.00  146
 56  \w     33.00 126.00   0.50    8.00    --   96.59-144.00  90.00  186
 57  \w   -104.00 -21.00   0.50    2.00    --  -40.91 -63.00   0.00  166
 58  \w   -104.00 -21.00   0.50    2.00    --  -40.91 -63.00 150.00  166
 59  \w    -97.00 -14.00   0.50    2.00    --  -40.91 138.00  90.00  166
 60  \w   -104.00 -21.00   0.50    2.00    --  -40.91 -63.00 -90.00  166
 61  \w   -104.00 -25.00   0.50    2.00    --  -40.91 -50.00 -60.00  158
 62  \w   -104.00 -21.00   0.50    2.00    --  -40.91 -63.00  90.00  166
 63  \w    -53.00  23.00   0.50    2.00    --  -40.91  37.00  90.00  152
 64  \w   -109.00 -32.00   0.50    2.00    --  -40.91 -25.00  30.00  154
 65  \w    -23.00  53.00   0.50    2.00    --   40.91 -37.00 120.00  152
 66  \w     15.00  42.00   0.50    2.00    --   40.91  77.00 118.39   54
 67  \w     15.00  42.00   0.50    2.00    --   40.91  81.00 134.28   54
 68  \w     16.00  42.00   0.50    2.00    --   40.91  80.00-139.26   52
 69  \w     15.00  42.00   0.50    2.00    --   40.91  81.00  76.85   54
 70  \w     16.00  42.00   0.50    2.00    --   40.91  78.00 -96.89   52
 71  \w     16.00  42.00   0.50    2.00    --   40.91  79.00 -53.73   52
 72  \w     15.00  42.00   0.50    2.00    --   40.91  82.00   2.26   54
 73  \w     16.00  42.00   0.50    2.00    --   40.91  80.00 -61.64   52
 74  \w     75.00 143.00   0.50    8.00    --   96.59  68.00-180.00  136
 75  \w     75.00 157.00   0.50    8.00    --   96.59  69.00  40.32  164
 76  \w     75.00 157.00   0.50    8.00    --   96.59  68.00 120.00  164
;
_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      0.0026621000
_diffrn_orient_matrix_UB_12      -0.0017833000
_diffrn_orient_matrix_UB_13      0.0722668000
_diffrn_orient_matrix_UB_21      0.0976591000
_diffrn_orient_matrix_UB_22      0.0436728000
_diffrn_orient_matrix_UB_23      0.0088710000
_diffrn_orient_matrix_UB_31      -0.0639404000
_diffrn_orient_matrix_UB_32      0.0611370000
_diffrn_orient_matrix_UB_33      0.0148911000
_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  0.0877
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            109597
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.582
_diffrn_reflns_theta_min         2.131
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.855
_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    1.157
_exptl_crystal_description       block
_exptl_crystal_F_000             2152
_exptl_crystal_size_max          0.331
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.293
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1335
_refine_ls_number_reflns         21044
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.295
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.1103
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3212
_refine_ls_wR_factor_ref         0.3433
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15041
_reflns_number_total             21044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02255a2.cif
_cod_data_source_block           etp5a+c4dincdcm-meoh-150k
_cod_database_code               7130167
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C61H78O10N2
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.821
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C122-N4
 1.1 with sigma of 0.02
 C121-N4
 1.4 with sigma of 0.02
 N3-C117
 1.1 with sigma of 0.02
 C118-N3
 1.4 with sigma of 0.02
 C120-C119
 1.5 with sigma of 0.02
 C119-C118
 1.5 with sigma of 0.02
 C121-C120
 1.5 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C118, C119, C120, C121
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C118, N3, C117
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C122, N4, C121
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C1(H1A,H1B), C45(H45A,H45B), C23(H23A,H23B), C34(H34A,H34B),
 C41(H41A,H41B), C54(H54A,H54B), C30(H30A,H30B), C19(H19A,H19B), C10(H10A,H10B),
  C8(H8A,H8B), C52(H52A,H52B), C106(H10C,H10D), C84(H84A,H84B), C95(H95A,H95B),
 C43(H43A,H43B), C113(H11D,H11E), C21(H21A,H21B), C73(H73A,H73B), C82(H82A,
 H82B), C80(H80A,H80B), C69(H69A,H69B), C93(H93A,H93B), C102(H10E,H10F),
 C57(H57A,H57B), C62(H62A,H62B), C104(H10G,H10H), C60(H60A,H60B), C91(H91A,
 H91B), C115(H11I,H11J), C32(H32A,H32B), C59(H59A,H59B), C71(H71A,H71B),
 C58(H58A,H58B), C121(H12C,H12D), C118(H11N,H11O), C119(H11P,H11Q), C120(H12E,
 H12F)
4.b Aromatic/amide H refined with riding coordinates:
 C28(H28), C3(H3), C17(H17), C39(H39), C47(H47), C14(H14), C6(H6), C50(H50),
 C25(H25), C36(H36), C67(H67), C111(H111), C78(H78), C89(H89), C100(H100),
 C86(H86), C75(H75), C97(H97), C64(H64), C108(H108)
4.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C31(H31A,H31B,H31C), C55(H55A,H55B,H55C), C83(H83A,H83B,
 H83C), C81(H81A,H81B,H81C), C94(H94A,H94B,H94C), C22(H22A,H22B,H22C), C53(H53A,
 H53B,H53C), C44(H44A,H44B,H44C), C114(H11F,H11G,H11H), C9(H9A,H9B,H9C),
 C11(H11A,H11B,H11C), C42(H42A,H42B,H42C), C70(H70A,H70B,H70C), C105(H10I,H10J,
 H10K), C103(H10L,H10M,H10N), C33(H33A,H33B,H33C), C72(H72A,H72B,H72C),
 C92(H92A,H92B,H92C), C116(H11K,H11L,H11M)
;
_shelx_res_checksum              32169
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.910
_oxdiff_exptl_absorpt_empirical_full_min 0.576