Styrene Purification by Guest-Induced Restructuring of Pillar[6]arene.
Jie, Kecheng; Liu, Ming; Zhou, Yujuan; Little, Marc A.; Bonakala, Satyanarayana; Chong, Samantha Y.; Stephenson, Andrew; Chen, Linjiang; Huang, Feihe; Cooper, Andrew I.; Journal of the American Chemical Society 139 (2017) 2908–2911; doi:10.1021/jacs.6b13300

data_4125599
_publ_section_title
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 Styrene Purification by Guest-Induced Restructuring of Pillar[6]arene.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2908
_journal_page_last               2911
_journal_paper_doi               10.1021/jacs.6b13300
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         '2(C55 H70 O10), 2.5(C8 H10)'
_chemical_formula_sum            'C130 H165 O20'
_chemical_formula_weight         2047.61
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_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                90
_cell_angle_beta                 96.4750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5000(8)
_cell_length_b                   20.6046(12)
_cell_length_c                   43.205(3)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    240
_cell_measurement_theta_max      23.663
_cell_measurement_theta_min      2.193
_cell_volume                     11941.3(13)
_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
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            71695
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        23.200
_diffrn_reflns_theta_max         23.255
_diffrn_reflns_theta_min         0.949
_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    0.075
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.7040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0726 before and 0.0534 after correction.
The Ratio of minimum to maximum transmission is 0.7585.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_description       block
_exptl_crystal_F_000             4420
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.241
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1402
_refine_ls_number_reflns         17119
_refine_ls_number_restraints     181
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0865
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1428P)^2^+7.3177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2383
_refine_ls_wR_factor_ref         0.2840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11208
_reflns_number_total             17119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b13300_si_003.cif
_cod_data_source_block           pillar5arene-et_ethylbenzene
_cod_depositor_comments          'Adding full bibliography for 4125599.cif.'
_cod_original_cell_volume        11941.2(12)
_cod_database_code               4125599
_olex2_refinement_description
;
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, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C119-C125 = C133-C127
 1.51 with sigma of 0.01
 C62-C59
 1.51 with sigma of 0.01
 C63-C62
 1.54 with sigma of 0.01
 C48-C2BA = C49-C48
 1.54 with sigma of 0.01
 C126-C125 = C134-C133
 1.54 with sigma of 0.01
 C138-C136
 1.54 with sigma of 0.01
 C136-C135
 1.51 with sigma of 0.01
 C136-C137_$1 = C136-C135 = C135-C137 = C136_$1-C137
 1.39 with sigma of 0.01
 C138-C136
 1.49 with sigma of 0.01
 C138-C140
 1.54 with sigma of 0.015
 C140-C139_$1
 1.54 with sigma of 0.015
 C127-C134
 2.6 with sigma of 0.02
 C127-C134
 2.6 with sigma of 0.02
 C136-C140
 2.6 with sigma of 0.02
 C132-C133 \\sim C133-C128
 with sigma of 0.02
 C136-C139_$1 \\sim C139_$1-C135_$1
 with sigma of 0.02
3. Restrained planarity
 C132, C127, C128, C133, C131, C129, C130
 with sigma of 0.001
 C135_$1, C137_$1, C136, C135, C137, C136_$1, C139_$1, C138
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C136) \\sim Ueq, Uanis(C135) \\sim Ueq, Uanis(C137) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C59, C58, C60, C62, C57, C61, C63, C56
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C119, C124, C120, C123, C121, C122
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C127, C132, C128, C131, C129, C130
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C139, C137, C135, C136
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C136, C135, C137
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Others
 Fixed Sof: H48C(0.5) H48D(0.5) H48A(0.5) H48B(0.5) H137(0.75) C125(0.5)
 H12A(0.5) H12B(0.5) C127(0.5) C132(0.5) H132(0.5) C131(0.5) H131(0.5)
 C130(0.5) H130(0.5) C129(0.5) H129(0.5) C128(0.5) H128(0.5) H136(0.75)
 C2BA(0.5) H2BA(0.5) H2BB(0.5) H2BC(0.5) C49(0.5) H49A(0.5) H49B(0.5) H49C(0.5)
 C133(0.5) H13A(0.5) H13B(0.5) C134(0.5) H13C(0.5) H13D(0.5) H13E(0.5)
 C126(0.5) H12C(0.5) H12D(0.5) H12E(0.5) C119(0.5) C124(0.5) H124(0.5)
 C123(0.5) H123(0.5) C122(0.5) H122(0.5) C121(0.5) H121(0.5) C120(0.5)
 H120(0.5) C139(0.25) H13G(0.25) H13H(0.25) C138(0.25) H13I(0.25) H13J(0.25)
 C140(0.5) H14A(0.25) H14C(0.25) H14B(0.25) H13F(0.25) H14D(0.25) H14E(0.25)
 Fixed X: H14A(0.72203) H14C(0.63717) H14B(0.671141) H13F(0.7126)
 H14D(0.664381) H14E(0.59577)
 Fixed Y: H14A(0.48366) H14C(0.5246) H14B(0.54228) H13F(0.51585) H14D(0.46224)
 H14E(0.51466)
 Fixed Z: H14A(0.58215) H14C(0.59555) H14B(0.56266) H13F(0.59351)
 H14D(0.57021) H14E(0.58408)
7.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C98(H98A,H98B), C8(H8A,H8B), C77(H77A,H77B), C91(H91A,H91B),
 C70(H70A,H70B), C84(H84A,H84B), C38(H38A,H38B), C22(H22A,H22B), C15(H15A,H15B),
  C29(H29A,H29B), C115(H11A,H11B), C101(H10A,H10B), C109(H10C,H10D), C54(H54A,
 H54B), C107(H10H,H10I), C117(H11F,H11G), C40(H40A,H40B), C46(H46A,H46B),
 C99(H99A,H99B), C111(H11H,H11I), C52(H52A,H52B), C105(H10M,H10N), C50(H50A,
 H50B), C42(H42A,H42B), C44(H44A,H44B), C36(H36A,H36B), C103(H10R,H10S),
 C113(H11S,H11T), C48(H48C,H48D), C48(H48A,H48B), C62(H62A,H62B), C125(H12A,
 H12B), C133(H13A,H13B), C139(H13G,H13H), C138(H13I,H13J)
7.b Me refined with riding coordinates:
 C134(H13C,H13D,H13E)
7.c Aromatic/amide H refined with riding coordinates:
 C66(H66), C76(H76), C6(H6), C69(H69), C3(H3), C80(H80), C10(H10), C97(H97),
 C13(H13), C73(H73), C20(H20), C94(H94), C27(H27), C87(H87), C24(H24), C34(H34),
  C83(H83), C31(H31), C90(H90), C17(H17), C58(H58), C57(H57), C56(H56),
 C61(H61), C60(H60), C137(H137), C135(H135), C132(H132), C131(H131), C130(H130),
  C129(H129), C128(H128), C136(H136), C124(H124), C123(H123), C122(H122),
 C121(H121), C120(H120)
7.d Fitted hexagon refined as free rotating group:
 C59(C58,C57,C56,C61,C60), C127(C132,C131,C130,C129,C128), C119(C124,C123,C122,
 C121,C120)
7.e Idealised Me refined as rotating group:
 C108(H10E,H10F,H10G), C110(H11C,H11D,H11E), C55(H55A,H55B,H55C), C39(H39A,
 H39B,H39C), C47(H47A,H47B,H47C), C102(H10J,H10K,H10L), C116(H11J,H11K,H11L),
 C112(H11M,H11N,H11O), C118(H11P,H11Q,H11R), C51(H51A,H51B,H51C), C41(H41A,H41B,
 H41C), C106(H10O,H10P,H10Q), C104(H10T,H10U,H10V), C53(H53A,H53B,H53C),
 C43(H43A,H43B,H43C), C100(H10W,H10X,H10Y), C37(H37A,H37B,H37C), C45(H45A,H45B,
 H45C), C63(H63A,H63B,H63C), C114(H11U,H11V,H11W), C2BA(H2BA,H2BB,H2BC),
 C49(H49A,H49B,H49C), C126(H12C,H12D,H12E)
;
_plat027_alert_3_a
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Problem:  _diffrn_reflns_theta_full (too) Low ............ 23.20 Degree
Response: Due to disorder the single crystal was weakly diffracting and a 
suitable resolution limit of 0.85 ang. was applied during refinement. 
;
_plat413_alert_2_a
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Problem:  Short Inter XH3 .. XHn H36A .. H49A .. 1.83 Ang.
Response: In the crystal structure the ethyl groups of EtP5 were disordered
and one -CH3 group was modelled over two positions. Due to disorder, 
and the limited resolution of the diffraction data, it was not possible to 
accurately determine H-atom positions. H-atoms were therefore placed in 
estimated positions are refined using the riding model. The estimated 
positions of disordered -CH2- group H-atom H36A and disordered -CH3 group 
H-atom H49A are unlikely to be correct resulting in this close intermolecular 
H-H contact.    THETM01_ALERT_3_B 
Problem: The value of sine(theta_max)/wavelength is less than 0.575
Calculated sin(theta_max)/wavelength = 0.5555
Response: Due to disorder the single crystal was weakly diffracting and a 
suitable resolution limit of 0.85 ang. was applied during refinement.
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_plat410_alert_2_b
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Problem:  Short Intra H...H Contact H24 .. H48C .. 1.81 Ang.
Response: In the crystal structure the ethyl groups of EtP5 were disordered
and one -CH3 group was modelled over two positions. Due to disorder, 
and the limited resolution of the diffraction data, it was not possible to 
accurately determine H-atom positions. H-atoms were therefore placed in 
estimated positions are refined using the riding model. The estimated 
positions of disordered -CH2- group H-atom H48C is unlikely to be correct 
resulting in a close intramolecular H-H contact with aryl C-H H-atom H24.   
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_shelx_res_checksum              98107
_shelx_hkl_checksum              25137
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'