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_7130170
_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         'C7 H4 I N, C55 H70 O10, C H Cl3'
_chemical_formula_sum            'C63 H75 Cl3 I N O10'
_chemical_formula_weight         1239.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-17
_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                 120.0360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.60810(10)
_cell_length_b                   21.52620(10)
_cell_length_c                   27.6794(3)
_cell_measurement_reflns_used    29588
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      68.4550
_cell_measurement_theta_min      2.7350
_cell_volume                     5987.67(11)
_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 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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     19.00 105.00   0.50    0.20    --   40.91  69.00  70.00  172
  2  \w    -23.00  63.00   0.50    0.20    --   40.91 -69.00 -62.00  172
  3  \w     75.00 157.00   0.50    0.77    --   96.90  69.00  70.00  164
  4  \w     33.00 119.00   0.50    0.77    --   96.90 -69.00 -62.00  172
  5  \w    -53.00  23.00   0.50    0.20    --  -40.91  37.00-150.00  152
  6  \w   -105.00 -29.00   0.50    0.20    --  -40.91 -37.00-180.00  152
  7  \w   -105.00 -19.00   0.50    0.20    --  -40.91 -69.00 -62.00  172
  8  \w    -63.00  23.00   0.50    0.20    --  -40.91  69.00  70.00  172
  9  \w    -53.00  23.00   0.50    0.20    --  -40.91  37.00  60.00  152
 10  \w    -50.00  27.00   0.50    0.20    --  -40.91  25.00 -30.00  154
 11  \w     29.00 105.00   0.50    0.20    --   40.91  37.00  30.00  152
 12  \w    -13.00  77.00   0.50    0.20    --   40.91-104.00 120.00  180
 13  \w    -13.00  77.00   0.50    0.20    --   40.91-104.00 -60.00  180
 14  \w     29.00 105.00   0.50    0.20    --   40.91  37.00-120.00  152
 15  \w     88.00 157.00   0.50    0.77    --   96.90  33.00 120.00  138
 16  \w     32.00 106.00   0.50    0.77    --   96.90 -33.00  90.00  148
 17  \w     34.00 110.00   0.50    0.77    --   96.90 -42.00 -60.00  152
 18  \w     34.00 113.00   0.50    0.77    --   96.90 -50.00  30.00  158
 19  \w     88.00 157.00   0.50    0.77    --   96.90  25.00 150.00  138
 20  \w     88.00 157.00   0.50    0.77    --   96.90  33.00-180.00  138
 21  \w     83.00 157.00   0.50    0.77    --   96.90  77.00-180.00  148
 22  \w     83.00 157.00   0.50    0.77    --   96.90  77.00   0.00  148
 23  \w     88.00 157.00   0.50    0.77    --   96.90  33.00   0.00  138
 24  \w     34.00 113.00   0.50    0.77    --   96.90 -50.00-180.00  158
 25  \w     32.00 109.00   0.50    0.77    --   96.90-117.00 -30.00  154
 26  \w     76.00 151.00   0.50    0.77    --   96.90  68.00-150.00  150
 27  \w     62.00 113.00   0.50    0.77    --   96.90 -68.00  90.00  102
 28  \w     96.00 149.00   0.50    0.77    --   96.90  77.00  30.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            48172
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.551
_diffrn_reflns_theta_min         2.759
_exptl_absorpt_coefficient_mu    5.902
_exptl_absorpt_correction_T_max  0.459
_exptl_absorpt_correction_T_min  0.207
_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    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             2576
_exptl_crystal_size_max          0.414
_exptl_crystal_size_mid          0.318
_exptl_crystal_size_min          0.238
_refine_diff_density_max         2.183
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.00015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     774
_refine_ls_number_reflns         10951
_refine_ls_number_restraints     263
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0612P)^2^+6.5669P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10067
_reflns_number_total             10951
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02255a2.cif
_cod_data_source_block           etp5a+i-nc-150k
_cod_original_cell_volume        5987.67(10)
_cod_database_code               7130170
_shelx_shelxl_version_number     2014/7
_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
 O8-C43A \\sim O8-C43B
 with sigma of 0.02
 I1-C60 \\sim I1A-C60A
 with sigma of 0.02
 C43A-C44A \\sim C43B-C44B
 with sigma of 0.02
 C57-C59 \\sim C57A-C59A
 with sigma of 0.04
 N1-C57 \\sim N1A-C57A
 with sigma of 0.02
 O8-C44A \\sim O8-C44B
 with sigma of 0.04
 Cl2A-Cl1 \\sim Cl2B-Cl1A
 with sigma of 0.04
 C60-C59 \\sim C60A-C59A
 with sigma of 0.02
 Cl3A-C63 \\sim Cl3B-C63A
 with sigma of 0.02
 Cl2A-Cl3A \\sim Cl2B-Cl3B
 with sigma of 0.04
 C60-C61 \\sim C60A-C61A
 with sigma of 0.02
 Cl3A-Cl1 \\sim Cl3B-Cl1A
 with sigma of 0.04
 Cl1-C63 \\sim Cl1A-C63A
 with sigma of 0.02
 C62-C58 \\sim C62A-C58A
 with sigma of 0.04
 Cl2A-C63 \\sim Cl2B-C63A
 with sigma of 0.02
 C60-C58 \\sim C60A-C58A
 with sigma of 0.04
 C59-C58 \\sim C59A-C58A
 with sigma of 0.02
 C57-C61 \\sim C57A-C61A
 with sigma of 0.04
 C61-C62 \\sim C61A-C62A
 with sigma of 0.02
 C59-C61 \\sim C59A-C61A
 with sigma of 0.04
 I1-C59 \\sim I1A-C59A
 with sigma of 0.04
 I1-C61 \\sim I1A-C61A
 with sigma of 0.04
 N1-C62 \\sim N1A-C62A
 with sigma of 0.04
 C57-C56 \\sim C57A-C56A
 with sigma of 0.04
 N1-C58 \\sim N1A-C58A
 with sigma of 0.04
 C57-C62 \\sim C57A-C62A
 with sigma of 0.02
 C57-C58 \\sim C57A-C58A
 with sigma of 0.02
 C60-C62 \\sim C60A-C62A
 with sigma of 0.04
 I1A-C56A \\sim I1-C56
 with sigma of 0.001
 N1-C56 \\sim N1A-C56A
 with sigma of 0.001
 N1A-C57A \\sim N1-C57
 with sigma of 0.001
 C56-C57 \\sim C57A-C56A
 with sigma of 0.001
3. Restrained planarity
 C57A, N1A, C56A, C58A
 with sigma of 0.1
 C59A, I1A, C60A, C61A, C58A, C62A, C57A, N1A, C56A
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
C62A \\sim I1A \\sim C60A \\sim C59A \\sim C61A \\sim C58A \\sim C57A \\sim N1A
\\sim C56A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
Uanis(C61) \\sim Ueq, Uanis(I1) \\sim Ueq, Uanis(C60) \\sim Ueq, Uanis(C59)
\\sim Ueq, Uanis(C62) \\sim Ueq, Uanis(C58) \\sim Ueq, Uanis(C57) \\sim Ueq,
Uanis(N1) \\sim Ueq, Uanis(C56) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C57) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C63A) \\sim Ueq, Uanis(Cl2B) \\sim Ueq, Uanis(Cl3B) \\sim Ueq,
Uanis(Cl1A) \\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(Cl2A) \\sim Ueq, Uanis(Cl3A)
\\sim Ueq, Uanis(Cl1) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
5. Rigid body (RIGU) restrains
 Cl1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 Cl1, Cl3A, Cl2A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C63
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl3A, Cl2A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl3A, C63, Cl2A, Cl1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl1, C63
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O8, C43B, C44B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O8, C43A, C44A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 Cl2A, C63, Cl3A, Cl1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C63A, Cl2B, Cl3B, Cl1A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C60, I1, C61, C59, C62, C58, C57, N1, C56
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(I1A)=Sof(C57A)=Sof(C58A)=Sof(H58A)=Sof(C59A)=Sof(H59A)=Sof(C60A)=
 Sof(C61A)=Sof(H61A)=Sof(C62A)=Sof(H62A)=Sof(N1A)=Sof(C56A)=1-FVAR(1)
 Sof(I1)=Sof(N1)=Sof(C57)=Sof(C62)=Sof(H62)=Sof(C61)=Sof(H61)=Sof(C60)=
 Sof(C59)=Sof(H59)=Sof(C58)=Sof(H58)=Sof(C56)=FVAR(1)
 Sof(C63A)=Sof(H63A)=Sof(Cl2B)=Sof(Cl3B)=Sof(Cl1A)=1-FVAR(2)
 Sof(Cl2A)=Sof(Cl3A)=Sof(Cl1)=Sof(C63)=Sof(H63)=FVAR(2)
 Fixed Sof: C43A(0.6) H43A(0.6) H43B(0.6) C44A(0.6) H44A(0.6) H44B(0.6)
 H44C(0.6) C43B(0.4) H43C(0.4) H43D(0.4) C44B(0.4) H44D(0.4) H44E(0.4) H44F(0.4)
 Fixed Uiso: I1A(0.06) C57A(0.06) C58A(0.06) C59A(0.06) C60A(0.06) C61A(0.06)
 C62A(0.06) N1A(0.06) C56A(0.06)
7.a Ternary CH refined with riding coordinates:
 C63(H63), C63A(H63A)
7.b Secondary CH2 refined with riding coordinates:
 C52(H52A,H52B), C23(H23A,H23B), C12(H12A,H12B), C34(H34A,H34B), C10(H10A,
 H10B), C19(H19A,H19B), C1(H1A,H1B), C45(H45A,H45B), C30(H30A,H30B), C32(H32A,
 H32B), C54(H54A,H54B), C21(H21A,H21B), C8(H8A,H8B), C41(H41A,H41B), C43A(H43A,
 H43B), C43B(H43C,H43D)
7.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C25(H25), C28(H28), C17(H17), C47(H47), C6(H6), C39(H39), C3(H3),
 C50(H50), C36(H36), C62(H62), C61(H61), C59(H59), C58(H58), C58A(H58A),
 C59A(H59A), C61A(H61A), C62A(H62A)
7.d Fitted hexagon refined as free rotating group:
 C57(C62,C61,C60,C59,C58), C57A(C58A,C59A,C60A,C61A,C62A)
7.e Idealised Me refined as rotating group:
 C53(H53A,H53B,H53C), C55(H55A,H55B,H55C), C11(H11A,H11B,H11C), C33(H33A,H33B,
 H33C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C31(H31A,H31B,H31C), C9(H9A,
 H9B,H9C), C42(H42A,H42B,H42C), C44A(H44A,H44B,H44C), C44B(H44D,H44E,H44F)
;
_shelx_res_checksum              13424
_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
;