Near-Ideal Xylene Selectivity in Adaptive Molecular Pillar[ n]arene Crystals.
Jie, Kecheng; Liu, Ming; Zhou, Yujuan; Little, Marc A.; Pulido, Angeles; Chong, Samantha Y.; Stephenson, Andrew; Hughes, Ashlea R.; Sakakibara, Fumiyasu; Ogoshi, Tomoki; Blanc, Frédéric; Day, Graeme M.; Huang, Feihe; Cooper, Andrew I.; Journal of the American Chemical Society 140 (2018) 6921–6930; doi:10.1021/jacs.8b02621

data_4132263
_publ_section_title
;
 Near-Ideal Xylene Selectivity in Adaptive Molecular Pillar[ n]arene
 Crystals.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6921
_journal_page_last               6930
_journal_paper_doi               10.1021/jacs.8b02621
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         '2(C55 H70 O10), 3.49(C8 H10)'
_chemical_formula_sum            'C137.88 H174.85 O20'
_chemical_formula_weight         2152.11
_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
_audit_creation_date             2016-03-02
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                76.973(2)
_cell_angle_beta                 84.468(2)
_cell_angle_gamma                84.137(2)
_cell_formula_units_Z            2
_cell_length_a                   14.0646(13)
_cell_length_b                   21.414(2)
_cell_length_c                   21.8397(19)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    240
_cell_measurement_theta_max      21.342
_cell_measurement_theta_min      2.321
_cell_volume                     6356.6(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      240.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            63348
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        21.966
_diffrn_reflns_theta_max         21.966
_diffrn_reflns_theta_min         0.960
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.7579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0949 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.8166.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_description       block
_exptl_crystal_F_000             2324
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1533
_refine_ls_number_reflns         15388
_refine_ls_number_restraints     301
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0525
_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^)+(0.0693P)^2^+2.4648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1562
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10230
_reflns_number_total             15388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b02621_si_006.cif
_cod_data_source_block           pillar_5_arene_meta_xylene
_cod_original_cell_volume        6356.7(10)
_cod_database_code               4132263
_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
 C141-C144 = C143-C137
 1.49 with sigma of 0.01
 C9B-C10B
 1.54 with sigma of 0.01
 C142-C144 \\sim C144-C140
 with sigma of 0.02
 C142-C143 \\sim C143-C138
 with sigma of 0.02
3. Restrained planarity
 C137, C138, C139, C140, C141, C142, C143, C144
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C9B) \\sim Ueq, Uanis(C10B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C54) \\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(C56)
\\sim Ueq, Uanis(O11) \\sim Ueq, Uanis(O10) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C113, C114, C115, C116, C117, C118, C119, C120
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C129, C130, C131, C132, C133, C134, C135, C136
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C137, C138, C139, C140, C141, C142, C143, C144
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O21, C9B, C10B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O10, C56, C57
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O11, C54, C55
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C121, C122, C123, C124, C125, C126, C127, C128
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Others
 Sof(O11)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(H55C)=
 1-FVAR(1)
 Sof(O10)=Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(C57)=Sof(H57A)=Sof(H57B)=Sof(H57C)=
 FVAR(1)
 Sof(O21)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=Sof(C10B)=Sof(H10X)=Sof(H10Y)=Sof(H)=1-
 FVAR(2)
 Sof(O20)=Sof(C109)=Sof(H10Z)=Sof(HA)=Sof(C110)=Sof(H11F)=Sof(H11G)=Sof(H11H)=
 Sof(C141)=Sof(C142)=Sof(H142)=Sof(C137)=Sof(C138)=Sof(H138)=Sof(C139)=
 Sof(H139)=Sof(C140)=Sof(H140)=Sof(C143)=Sof(H14C)=Sof(H14D)=Sof(H14E)=
 Sof(C144)=Sof(H14F)=Sof(H14G)=Sof(H14H)=FVAR(2)
7.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C21(H21A,H21B), C28(H28A,H28B), C35(H35A,H35B),
 C36(H36A,H36B), C38(H38A,H38B), C40(H40A,H40B), C42(H42A,H42B), C44(H44A,H44B),
  C46(H46A,H46B), C48(H48A,H48B), C50(H50A,H50B), C52(H52A,H52B), C56(H56A,
 H56B), C54(H54A,H54B), C64(H64A,H64B), C71(H71A,H71B), C78(H78A,H78B),
 C85(H85A,H85B), C92(H92A,H92B), C93(H93A,H93B), C95(H95A,H95B), C97(H97A,H97B),
  C99(H99A,H99B), C101(H10D,H10E), C103(H10I,H10J), C105(H10N,H10O), C107(H10S,
 H10T), C111(H11A,H11B), C9B(H9BA,H9BB), C109(H10Z,HA)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C12(H12), C16(H16), C19(H19), C23(H23), C26(H26),
 C30(H30), C33(H33), C58(H58), C61(H61), C66(H66), C69(H69), C73(H73), C76(H76),
  C80(H80), C83(H83), C87(H87), C90(H90), C131(H131), C132(H132), C133(H133),
 C135(H135), C122(H122), C123(H123), C124(H124), C126(H126), C115(H115),
 C116(H116), C117(H117), C119(H119), C142(H142), C138(H138), C139(H139),
 C140(H140)
7.c Fitted hexagon refined as free rotating group:
 C141(C142,C137,C138,C139,C140)
7.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C39(H39A,H39B,H39C), C41(H41A,H41B,H41C), C43(H43A,H43B,
 H43C), C45(H45A,H45B,H45C), C47(H47A,H47B,H47C), C49(H49A,H49B,H49C), C51(H51A,
 H51B,H51C), C53(H53A,H53B,H53C), C57(H57A,H57B,H57C), C55(H55A,H55B,H55C),
 C94(H94A,H94B,H94C), C96(H96A,H96B,H96C), C98(H98A,H98B,H98C), C100(H10A,H10B,
 H10C), C102(H10F,H10G,H10H), C104(H10K,H10L,H10M), C106(H10P,H10Q,H10R),
 C108(H10U,H10V,H10W), C112(H11C,H11D,H11E), C10B(H10X,H10Y,H), C110(H11F,H11G,
 H11H), C129(H12A,H12B,H12C), C136(H13A,H13B,H13C), C127(H12D,H12E,H12F),
 C128(H12G,H12H,H12I), C113(H11I,H11J,H11K), C120(H12J,H12K,H12L), C143(H14C,
 H14D,H14E), C144(H14F,H14G,H14H)
;
_shelx_res_checksum              91686
_shelx_hkl_checksum              96142
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'