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_7130169
_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, C12 H20 N2'
_chemical_formula_sum            'C67 H90 N2 O10'
_chemical_formula_weight         1083.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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                90
_cell_angle_beta                 100.5510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.23130(10)
_cell_length_b                   22.6354(2)
_cell_length_c                   20.6987(2)
_cell_measurement_reflns_used    30344
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      68.4010
_cell_measurement_theta_min      2.8950
_cell_volume                     6094.36(9)
_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 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_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    -83.00   1.00   0.50    0.36    --  -40.91 116.00-146.00  168
  2  \w   -105.00 -53.00   0.50    0.36    --  -40.91-162.00 -24.00  104
  3  \w   -111.00 -27.00   0.50    0.36    --  -40.91 162.00   2.00  168
  4  \w     54.00 105.00   0.50    0.36    --   40.91 162.00   2.00  102
  5  \w     -1.00  84.00   0.50    0.36    --   40.91-116.00 125.00  170
  6  \w     27.00 112.00   0.50    0.36    --   40.91-162.00 -24.00  170
  7  \w     32.00 108.00   0.50    1.44    --   96.59-116.00 125.00  152
  8  \w     53.00 156.00   0.50    1.44    --   96.59 162.00   2.00  206
  9  \w     81.00 157.00   0.50    1.44    --   96.59 116.00-146.00  152
 10  \w     32.00 136.00   0.50    1.44    --   96.59-162.00 -24.00  208
 11  \w    -97.00 -14.00   0.50    0.36    --  -40.91 138.00  90.00  166
 12  \w    -50.00  27.00   0.50    0.36    --  -40.91  25.00   0.00  154
 13  \w   -104.00 -25.00   0.50    0.36    --  -40.91 -50.00   0.00  158
 14  \w   -104.00 -25.00   0.50    0.36    --  -40.91 -50.00 -90.00  158
 15  \w    -57.00  22.00   0.50    0.36    --  -40.91  50.00-180.00  158
 16  \w     29.00 105.00   0.50    0.36    --   40.91  37.00-150.00  152
 17  \w    -23.00  53.00   0.50    0.36    --   40.91 -37.00   0.00  152
 18  \w     26.00  51.00   0.50    0.36    --   40.91 -37.00-120.00   50
 19  \w    -13.00  15.00   0.50    0.36    --   40.91 -37.00-120.00   56
 20  \w     48.00  74.00   0.50    0.36    --   40.91-138.00-180.00   52
 21  \w     34.00 123.00   0.50    1.44    --   96.59-144.00 -60.00  178
 22  \w     38.00  91.00   0.50    1.44    --   96.59 -96.00 -60.00  106
 23  \w     76.00 107.00   0.50    1.44    --   96.59-117.00-180.00   62
 24  \w     77.00 103.00   0.50    1.44    --   96.59 -33.00-120.00   52
 25  \w     88.00 155.00   0.50    1.44    --   96.59  25.00  30.00  134
 26  \w     72.00  98.00   0.50    1.44    --   96.59 -96.00-180.00   52
 27  \w     27.00  86.00   0.50    1.44    --   96.59 -96.00 120.00  118
 28  \w    116.00 157.00   0.50    1.44    --   96.59  96.00-180.00   82
 29  \w     85.00 111.00   0.50    1.44    --   96.59  96.00-180.00   52
 30  \w     33.00 108.00   0.50    1.44    --   96.59 -59.00 -60.00  150
 31  \w     77.00 157.00   0.50    1.44    --   96.59  68.00-150.00  160
 32  \w     39.00 109.00   0.50    1.44    --   96.59 -59.00  90.00  140
 33  \w     36.00 110.00   0.50    1.44    --   96.59 -17.00  60.00  148
;
_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      -0.0124866000
_diffrn_orient_matrix_UB_12      0.0661331000
_diffrn_orient_matrix_UB_13      0.0141867000
_diffrn_orient_matrix_UB_21      0.0274582000
_diffrn_orient_matrix_UB_22      -0.0123337000
_diffrn_orient_matrix_UB_23      0.0743534000
_diffrn_orient_matrix_UB_31      0.1145465000
_diffrn_orient_matrix_UB_32      0.0101909000
_diffrn_orient_matrix_UB_33      -0.0019402000
_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  0.0466
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            48466
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.552
_diffrn_reflns_theta_min         2.920
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.821
_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    1.181
_exptl_crystal_description       block
_exptl_crystal_F_000             2344
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.167
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     722
_refine_ls_number_reflns         11105
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0942P)^2^+3.4113P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.1750
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9586
_reflns_number_total             11105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02255a2.cif
_cod_data_source_block           etp5a+c10dinc+fib-2-1-2-150k
_cod_database_code               7130169
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         C67H90N2O10
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Restrained distances
 C57-N1
 1.42 with sigma of 0.02
 N2-C67
 1.15 with sigma of 0.02
 N2-C66
 1.42 with sigma of 0.02
 N1-C56
 1.15 with sigma of 0.02
2. Rigid body (RIGU) restrains
 C57, N1, C56
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C67, N2, C66
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C59, C58, C57
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C66, C65, C64
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C59, C60, C61, C62
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C19(H19A,H19B), C20(H20A,H20B),
 C22(H22A,H22B), C30(H30A,H30B), C31(H31A,H31B), C33(H33A,H33B), C41(H41A,H41B),
  C42(H42A,H42B), C44(H44A,H44B), C52(H52A,H52B), C53(H53A,H53B), C55(H55A,
 H55B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B),
 C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,H65B),
  C66(H66A,H66B)
3.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)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C21(H21A,H21B,
 H21C), C29(H29A,H29B,H29C), C32(H32A,H32B,H32C), C40(H40A,H40B,H40C), C43(H43A,
 H43B,H43C), C51(H51A,H51B,H51C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              37575
_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 2.257
_oxdiff_exptl_absorpt_empirical_full_min 0.700