Construction of [2]pseudorotaxane and [3]pseudorotaxane based on perbromoethylated pillar[5]arene/pyridinium iodide ion-pair recognition
Shao, Li; Hua, Bin; Liu, Jiyong; Huang, Feihe; Chemical Communications  (2019) –; doi:10.1039/C9CC01984G

data_7123175
_publ_section_title
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 Construction of [2]pseudorotaxane and [3]pseudorotaxane based on
 perbromoethylated pillar[5]arene/pyridinium iodide ion-pair recognition
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01984G
_journal_year                    2019
_chemical_formula_moiety         '2(C55 H60 Br10 O10), C15 H20 N2, 2(I)'
_chemical_formula_sum            'C125 H140 Br20 I2 N2 O20'
_chemical_formula_weight         3842.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-03-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-01 deposited with the CCDC.    2019-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                81.626(2)
_cell_angle_beta                 80.866(2)
_cell_angle_gamma                75.600(2)
_cell_formula_units_Z            1
_cell_length_a                   12.5317(9)
_cell_length_b                   15.7091(12)
_cell_length_c                   18.2229(15)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.84
_cell_measurement_theta_min      2.39
_cell_volume                     3409.4(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            56647
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.495
_diffrn_reflns_theta_min         2.393
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.384
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0841 before and 0.0505 after correction.
The Ratio of minimum to maximum transmission is 0.6096.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_description       block
_exptl_crystal_F_000             1870
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.118
_refine_diff_density_max         3.064
_refine_diff_density_min         -3.432
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     917
_refine_ls_number_reflns         13929
_refine_ls_number_restraints     688
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0703
_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^)+(0.1291P)^2^+12.4088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2075
_refine_ls_wR_factor_ref         0.2208
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10712
_reflns_number_total             13929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01984g2.cif
_cod_data_source_block           1
_cod_database_code               7123175
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C36-C55
 1.5 with sigma of 0.01
 O7-C36A = O7-C36 = C55-C36 = C55A-C36A
 1.5 with sigma of 0.01
 Br10-C55 = Br-C55A
 1.9 with sigma of 0.01
 O7-C55
 2.5 with sigma of 0.02
 O7-C55A
 2.5 with sigma of 0.02
 C36-Br10
 2.8 with sigma of 0.02
 C36A-Br
 2.8 with sigma of 0.02
 O2-C8A
 2.5 with sigma of 0.02
 Br2-C7
 2.9 with sigma of 0.02
 O4-C19A = O4-C19 = C20A-C19A = C20-C19
 1.5 with sigma of 0.02
 O4-C20
 2.5 with sigma of 0.02
 O4-C20A
 2.5 with sigma of 0.02
 Br4A-C20A = Br4-C20
 1.85 with sigma of 0.02
 C19A-Br4A
 2.9 with sigma of 0.02
 Br4-C19
 2.9 with sigma of 0.02
 Br9A-C52 = Br9-C52
 1.9 with sigma of 0.02
 O9-C46 = C47-C46
 1.5 with sigma of 0.01
 O10-C51 = C52-C51
 1.5 with sigma of 0.02
 Br4_$2-Br10
 2.3 with sigma of 0.02
 C60-C62
 2.5 with sigma of 0.02
 C56-C62
 2.5 with sigma of 0.02
 C63-C62 = C62-C61
 1.5 with sigma of 0.02
 C63-C61
 2.5 with sigma of 0.02
 C63-C56
 3.5 with sigma of 0.02
 C63_$1-C61_$1
 2.5 with sigma of 0.005
 C63-C63_$1
 1.5 with sigma of 0.001
 C63_$1-C62_$1
 1.5 with sigma of 0.001
 C62-C63
 1.5 with sigma of 0.001
 C71_$1-C59_$1
 2.5 with sigma of 0.02
 C71_$1-C57_$1
 2.5 with sigma of 0.01
 C71-C59
 2.5 with sigma of 0.02
 C71-C57
 2.5 with sigma of 0.02
 I11-C62_$1
 2.8 with sigma of 0.02
 C70_$1-C67_$1
 2.5 with sigma of 0.01
 C68_$1-C70_$1
 2.5 with sigma of 0.02
 Br2A-C8A = Br2-C8
 1.9 with sigma of 0.01
 O2-C8
 2.5 with sigma of 0.02
 C63-C64
 1.5 with sigma of 0.01
 C64-C66
 2.5 with sigma of 0.02
 N2-C70 = C65-C64
 1.5 with sigma of 0.01
 Br3-C15 = Br3A-C15
 1.9 with sigma of 0.02
 C7A-Br2A
 2.9 with sigma of 0.02
 O2-C7 = O2-C7A = C8A-C7A = C8-C7
 1.5 with sigma of 0.01
 H21-H19B
 2.01 with sigma of 0.01
3. Restrained planarity
 C57, N1, C59, C60, C61, C56, C62, C71
 with sigma of 0.01
 C64, C68, C69, C65, C66, C67, N2, C70
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C36 \\sim Br10 \\sim C55 \\sim C36A \\sim C55A \\sim Br: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
Br4 \\sim C19 \\sim C20 \\sim Br4A \\sim C19A \\sim C20A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
C27 \\sim C24 \\sim O5: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C67 \\sim C57 \\sim N1 \\sim C56 \\sim C59 \\sim C71 \\sim C61 \\sim C60 \\sim
C62 \\sim C63 \\sim C64 \\sim C65 \\sim C69 \\sim C66 \\sim C68 \\sim N2 \\sim
C70: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Br2 \\sim C7 \\sim C8 \\sim Br2A \\sim C7A \\sim C8A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C24) \\sim Ueq, Uanis(C27) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C27) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C67) \\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C56)
\\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C61) \\sim Ueq,
Uanis(C60) \\sim Ueq, Uanis(C62) \\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C64)
\\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C66) \\sim Ueq,
Uanis(C68) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C70) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(Br2) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(Br2A)
\\sim Ueq, Uanis(C7A) \\sim Ueq, Uanis(C8A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C24) = Uanis(O5)
5. Rigid body (RIGU) restrains
 C36, Br10, C55, C36A, C55A, Br
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Br4, C19, C20, Br4A, C19A, C20A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C27, C24, O5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C67, C57, N1, C56, C59, C71, C61, C60, C62, C63, C64, C65, C69, C66, C68, N2,
 C70
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Br2, C7, C8, Br2A, C7A, C8A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Others
 Sof(C36A)=Sof(H36C)=Sof(H36D)=Sof(C55A)=Sof(H55C)=Sof(H55D)=Sof(Br)=1-FVAR(1)
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(Br10)=Sof(C55)=Sof(H55A)=Sof(H55B)=FVAR(1)
 Sof(Br2A)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=1-FVAR(2)
 Sof(Br2)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8A)=Sof(H8B)=FVAR(2)
 Sof(Br4A)=Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20C)=Sof(H20D)=1-FVAR(3)
 Sof(Br4)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=FVAR(3)
 Sof(H15C)=Sof(H15D)=Sof(Br3A)=1-FVAR(4)
 Sof(Br3)=Sof(H15A)=Sof(H15B)=FVAR(4)
 Sof(H52C)=Sof(H52D)=Sof(Br9A)=1-FVAR(5)
 Sof(Br9)=Sof(H52A)=Sof(H52B)=FVAR(5)
 Fixed Sof: C57(0.5) H57(0.5) N1(0.5) C59(0.5) H59(0.5) C60(0.5) H60(0.5)
 C61(0.5) C56(0.5) H56(0.5) I11(0.55) I12(0.45) C62(0.5) H62A(0.5) H62B(0.5)
 C63(0.5) H63A(0.5) H63B(0.5) C71(0.5) H71A(0.5) H71B(0.5) H71C(0.5) C64(0.5)
 H64A(0.5) H64B(0.5) C68(0.5) H68(0.5) C69(0.5) H69(0.5) C65(0.5) C66(0.5)
 H66(0.5) C67(0.5) H67(0.5) N2(0.5) C70(0.5) H70A(0.5) H70B(0.5) H70C(0.5)
 Fixed U11: C5(0.008818)
 Fixed U12: C5(0.002775)
 Fixed U13: C5(-0.005243)
 Fixed U22: C5(0.023191)
 Fixed U23: C5(0.011006)
 Fixed U33: C5(0.03268)
7.a Riding coordinates:
 C7A(H7AA,H7AB), C64(H64A,H64B)
7.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C22(H22A,H22B), C14(H14A,H14B), C33(H33A,H33B), C43(H43A,
 H43B), C40(H40A,H40B), C1(H1A,H1B), C54(H54A,H54B), C52(H52A,H52B), C52(H52C,
 H52D), C41(H41A,H41B), C15(H15A,H15B), C15(H15C,H15D), C2(H2A,H2B), C31(H31A,
 H31B), C19(H19A,H19B), C46(H46A,H46B), C25(H25A,H25B), C30(H30A,H30B),
 C47(H47A,H47B), C26(H26A,H26B), C51(H51A,H51B), C7(H7A,H7B), C20(H20A,H20B),
 C8(H8A,H8B), C36(H36A,H36B), C55(H55A,H55B), C62(H62A,H62B), C63(H63A,H63B),
 C36A(H36C,H36D), C55A(H55C,H55D), C8A(H8AA,H8AB), C19A(H19C,H19D), C20A(H20C,
 H20D)
7.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C21(H21), C42(H42), C4(H4), C32(H32), C48(H48), C9(H9), C16(H16),
 C37(H37), C53(H53), C57(H57), C59(H59), C60(H60), C56(H56), C68(H68), C69(H69),
  C66(H66), C67(H67)
7.d Fitted hexagon refined as free rotating group:
 C57(N1,C59,C60,C61,C56), C68(C69,C65,C66,C67,N2)
7.e Idealised Me refined as rotating group:
 C71(H71A,H71B,H71C), C70(H70A,H70B,H70C)
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_shelx_res_checksum              82531
_olex2_submission_special_instructions 'No special instructions were received'