Molecular Barrel by a Hooping Strategy: Synthesis, Structure, and Selective CO2 Adsorption Facilitated by Lone Pair-π Interactions.
Wang, Qi-Qiang; Luo, Na; Wang, Xu-Dong; Ao, Yu-Fei; Chen, Yi-Fan; Liu, Jun-Min; Su, Cheng-Yong; Wang, De-Xian; Wang, Mei-Xiang; Journal of the American Chemical Society 139 (2017) 635–638; doi:10.1021/jacs.6b12386

data_4125761
_publ_section_title
;
 Molecular Barrel by a Hooping Strategy: Synthesis, Structure, and
 Selective CO2 Adsorption Facilitated by Lone Pair-\p Interactions.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              635
_journal_page_last               638
_journal_paper_doi               10.1021/jacs.6b12386
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C87 H90 N12 O12, 5(C H2 Cl2)'
_chemical_formula_sum            'C92 H100 Cl10 N12 O12'
_chemical_formula_weight         1920.33
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.71(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.036(4)
_cell_length_b                   14.730(3)
_cell_length_c                   39.096(8)
_cell_measurement_reflns_used    16720
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      1.7
_cell_volume                     10267(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear(Rigaku/MSC Inc., 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            68071
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         1.479
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4008
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_platon_squeeze_details
;
;
_refine_diff_density_max         1.031
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.0084(9)
_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   2.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1236
_refine_ls_number_reflns         17915
_refine_ls_number_restraints     293
_refine_ls_restrained_S_all      2.034
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.1145
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3043
_refine_ls_wR_factor_ref         0.3151
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14405
_reflns_number_total             17915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b12386_si_003.cif
_cod_data_source_block           r90428f
_cod_database_code               4125761
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.961
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 Cl3-Cl4 = Cl3'-Cl4' = Cl9-Cl10 = Cl11-Cl12
 2.8 with sigma of 0.01
 C96-Cl9 = C96-Cl10 = C97-Cl11 = C97-Cl12
 1.72 with sigma of 0.01
 C93-Cl3 = C93-Cl4 = C93'-Cl3' = C93'-Cl4'
 1.72 with sigma of 0.01
 C33'-C35' = C35'-C37'
 2.52 with sigma of 0.01
 C30'-C32' = C32'-C34' = C34'-C36' = C31'-C33'
 2.52 with sigma of 0.01
 C30-C32 = C32-C34 = C34-C36 = C31-C33 = C33-C35 = C35-C37
 2.52 with sigma of 0.01
 O3-C30 = O3-C30' = O4-C37 = O4-C37'
 1.42 with sigma of 0.01
 C35'-C36' = C36'-C37'
 1.54 with sigma of 0.01
 C30'-C31' = C31'-C32' = C32'-C33' = C33'-C34' = C34'-C35'
 1.54 with sigma of 0.01
 C30-C31 = C31-C32 = C32-C33 = C33-C34 = C34-C35 = C35-C36 = C36-C37
 1.54 with sigma of 0.01
 C8-C9 = C9-C10 = C10-C11 = C11-C12 = C12-C13 = C13-C14 = C14-C15
 1.54 with sigma of 0.01
 C8'-C9' = C9'-C10' = C10'-C11' = C11'-C12' = C12'-C13'
 1.54 with sigma of 0.01
 C8-C10 = C10-C12 = C12-C14 = C9-C11 = C11-C13 = C13-C15
 2.52 with sigma of 0.01
 C57-C56
 1.54 with sigma of 0.01
 C13'-C14' = C14'-C15'
 1.54 with sigma of 0.01
 C8'-C10' = C10'-C12' = C12'-C14' = C9'-C11' = C11'-C13' = C13'-C15'
 2.52 with sigma of 0.01
 O1-C8 = O1-C8' = O2-C15 = O2-C15'
 1.42 with sigma of 0.01
 C16-C15
 2.5 with sigma of 0.02
 C15'-C16
 2.5 with sigma of 0.02
3. Rigid bond restraints
 C17, C16
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C4, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C30 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C37:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C93) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(Cl4) \\sim Ueq, Uanis(C93')
\\sim Ueq, Uanis(Cl3') \\sim Ueq, Uanis(Cl4') \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C33)
\\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36) \\sim Ueq,
Uanis(C37) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C15) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C37) = Uanis(C37')
Uanis(C36) = Uanis(C36')
Uanis(C35) = Uanis(C35')
Uanis(C34) = Uanis(C34')
Uanis(C33) = Uanis(C33')
Uanis(C32) = Uanis(C32')
Uanis(C31) = Uanis(C31')
Uanis(C30) = Uanis(C30')
Uanis(C14) = Uanis(C14')
Uanis(C13) = Uanis(C13')
Uanis(C12) = Uanis(C12')
Uanis(C11) = Uanis(C11')
Uanis(C10) = Uanis(C10')
Uanis(C9) = Uanis(C9')
Uanis(C8) = Uanis(C8')
Uanis(C93) = Uanis(C93')
5. Others
 Sof(Cl11)=Sof(Cl12)=Sof(C97)=Sof(H97A)=Sof(H97B)=1-FVAR(1)
 Sof(Cl9)=Sof(Cl10)=Sof(C96)=Sof(H96A)=Sof(H96B)=FVAR(1)
 Sof(C30')=Sof(H30C)=Sof(H30D)=Sof(C31')=Sof(H31C)=Sof(H31D)=Sof(C32')=
 Sof(H32C)=Sof(H32D)=Sof(C33')=Sof(H33C)=Sof(H33D)=Sof(C34')=Sof(H34C)=
 Sof(H34D)=Sof(C35')=Sof(H35C)=Sof(H35D)=Sof(C36')=Sof(H36C)=Sof(H36D)=
 Sof(C37')=Sof(H37C)=Sof(H37D)=1-FVAR(2)
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32A)=
 Sof(H32B)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C35)=
 Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C37)=Sof(H37A)=Sof(H37B)=
 FVAR(2)
 Sof(C8')=Sof(H8'A)=Sof(H8'B)=Sof(C9')=Sof(H9'A)=Sof(H9'B)=Sof(C10')=Sof(H10C)=
 Sof(H10D)=Sof(C11')=Sof(H11C)=Sof(H11D)=Sof(C12')=Sof(H12C)=Sof(H12D)=
 Sof(C13')=Sof(H13C)=Sof(H13D)=Sof(C14')=Sof(H14C)=Sof(H14D)=Sof(C15')=
 Sof(H15C)=Sof(H15D)=1-FVAR(3)
 Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=
 Sof(H10B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=
 Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=
 FVAR(3)
 Sof(C93')=Sof(H93C)=Sof(H93D)=Sof(Cl3')=Sof(Cl4')=1-FVAR(4)
 Sof(C93)=Sof(H93A)=Sof(H93B)=Sof(Cl3)=Sof(Cl4)=FVAR(4)
 Fixed Uiso: C15'(0.1)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C8'(H8'A,H8'B),
  C9'(H9'A,H9'B), C10'(H10C,H10D), C11'(H11C,H11D), C12'(H12C,H12D), C13'(H13C,
 H13D), C14'(H14C,H14D), C15'(H15C,H15D), C22(H22A,H22B), C23(H23A,H23B),
 C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
  C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C30'(H30C,H30D), C31'(H31C,
 H31D), C32'(H32C,H32D), C33'(H33C,H33D), C34'(H34C,H34D), C35'(H35C,H35D),
 C36'(H36C,H36D), C37'(H37C,H37D), C44(H44A,H44B), C45(H45A,H45B), C52(H52A,
 H52B), C53(H53A,H53B), C54(H54A,H54B), C55(H55A,H55B), C56(H56A,H56B),
 C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C66(H66A,H66B), C92(H92A,H92B),
  C93(H93A,H93B), C93'(H93C,H93D), C94(H94A,H94B), C95(H95A,H95B), C96(H96A,
 H96B), C97(H97A,H97B)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C17(H17), C18(H18), C20(H20), C21(H21),
 C25(H25), C26(H26), C28(H28), C29(H29), C39(H39), C40(H40), C42(H42), C43(H43),
  C47(H47), C48(H48), C50(H50), C51(H51), C61(H61), C62(H62), C64(H64),
 C65(H65), C81(H81), C83(H83), C85(H85), C87(H87), C89(H89), C91(H91)
;
_shelx_res_checksum              23447
_shelx_hkl_checksum              15391
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'