Separation of Monochlorotoluene Isomers by Nonporous Adaptive Crystals of Perethylated Pillar[5]arene and Pillar[6]arene.
Wang, Mengbin; Zhou, Jiong; Li, Errui; Zhou, Yujuan; Li, Qing; Huang, Feihe; Journal of the American Chemical Society 141 (2019) 17102–17106; doi:10.1021/jacs.9b09988

data_4127859
_publ_section_title
;
 Separation of Monochlorotoluene Isomers by Nonporous Adaptive Crystals of
 Perethylated Pillar[5]arene and Pillar[6]arene.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17102
_journal_page_last               17106
_journal_paper_doi               10.1021/jacs.9b09988
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C66 H84 O12, C7 H7 Cl'
_chemical_formula_sum            'C73 H91 Cl O12'
_chemical_formula_weight         1195.90
_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   geom
_audit_creation_date             2019-07-21
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.927(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2674(5)
_cell_length_b                   12.9976(5)
_cell_length_c                   22.3812(11)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      3.04
_cell_volume                     3275.9(3)
_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      273.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            35208
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.425
_diffrn_reflns_theta_min         2.971
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0870 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.8845.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1284
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         6680
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0622
_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^)+(0.0950P)^2^+2.4671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1624
_refine_ls_wR_factor_ref         0.1852
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4926
_reflns_number_total             6680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09988_si_004.cif
_cod_data_source_block           a
_cod_database_code               4127859
_shelx_shelxl_version_number     2017/1
_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
 C1-C1S
 1.73 with sigma of 0.01
 C1S-C1
 1.53 with sigma of 0.02
 C6S-C1 \\sim C1-C2S
 with sigma of 0.02
3. Restrained planarity
 C1, C1S, C6S, C2S
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C2S \\sim C4S \\sim C5S \\sim C6S \\sim C3S \\sim C1S: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
C1 \\sim C1S \\sim C2S \\sim C6S \\sim C3S \\sim C5S \\sim C4S: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
Cl7S \\sim C1S \\sim C2S \\sim C6S \\sim C1 \\sim C3S \\sim C5S \\sim C4S:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq, Uanis(C1S) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
5. Others
 Fixed Sof: C1S(0.5) C2S(0.5) C3S(0.5) H3S(0.5) C4S(0.5) H4S(0.5) C5S(0.5)
 H5S(0.5) C6S(0.5) H6S(0.5) Cl7S(0.5) C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C14(H14A,H14B), C22(H22A,H22B), C32(H32A,H32B), C49(H49A,H49B),
 C51(H51A,H51B), C55(H55A,H55B), C56(H56A,H56B), C57(H57A,H57B)
6.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C17(H17), C21(H21), C26(H26), C27(H27), C3S(H3S),
 C4S(H4S), C5S(H5S), C6S(H6S)
6.c Fitted hexagon refined as free rotating group:
 C1S(C2S,C3S,C4S,C5S,C6S)
6.d Idealised Me refined as rotating group:
 C50(H50A,H50B,H50C), C52(H52A,H52B,H52C), C54(H54A,H54B,H54C), C58(H58A,H58B,
 H58C), C59(H59A,H59B,H59C), C61(H61A,H61B,H61C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              35985
_shelx_hkl_checksum              81096
_olex2_submission_special_instructions 'No special instructions were received'