Highly Selective Removal of Trace Isomers by Nonporous Adaptive Pillararene Crystals for Chlorobutane Purification.
Zhou, Yujuan; Jie, Kecheng; Zhao, Run; Li, Errui; Huang, Feihe; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c02684

data_4134587
_publ_section_title
;
 Highly Selective Removal of Trace Isomers by Nonporous Adaptive
 Pillararene Crystals for Chlorobutane Purification.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02684
_journal_year                    2020
_chemical_formula_moiety         'C66 H84 O12, C4 H9 Cl'
_chemical_formula_sum            'C70 H93 Cl O12'
_chemical_formula_weight         1161.89
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                79.480(5)
_cell_angle_beta                 74.424(5)
_cell_angle_gamma                65.366(5)
_cell_formula_units_Z            2
_cell_length_a                   12.3608(10)
_cell_length_b                   14.6450(12)
_cell_length_c                   23.0103(17)
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    102(2)
_cell_measurement_theta_max      55.33
_cell_measurement_theta_min      3.26
_cell_volume                     3635.4(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      102.36
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.0897
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            40930
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.785
_diffrn_reflns_theta_min         2.897
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1575 before and 0.1016 after correction. The Ratio of minimum to maximum transmission is 0.6197. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.061
_exptl_crystal_description       block
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.361
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       0.0303(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     810
_refine_ls_number_reflns         13630
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      0.890
_refine_ls_R_factor_all          0.2539
_refine_ls_R_factor_gt           0.2134
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+50.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4221
_refine_ls_wR_factor_ref         0.4429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8708
_reflns_number_total             13630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02684_si_003.cif
_cod_data_source_block           zyj20181123_0m
_cod_database_code               4134587
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.944
_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
 C6-C3
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl01 \\sim C6 \\sim C3 \\sim C4 \\sim C1: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Cl02 \\sim C5 \\sim C0AA \\sim C2 \\sim C1AA: within 2A with sigma of 0.001 and
sigma for terminal atoms of 0.002
C5 \\sim Cl02 \\sim C2 \\sim C1AA \\sim C0AA: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: Cl01(0.5) Cl02(0.5) C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C2(0.5)
 H2A(0.5) H2B(0.5) C3(0.5) H3A(0.5) H3B(0.5) H3C(0.5) C4(0.5) H4A(0.5) H4B(0.5)
 C5(0.5) H5(0.5) C6(0.5) H6(0.5) C1AA(0.5) H1AB(0.5) H1AC(0.5) H1AD(0.5)
 C0AA(0.5) H0AB(0.5) H0AC(0.5) H0AD(0.5)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6)
5.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B), C00V(H00C,H00E), C00W(H00G,H00H), C014(H01A,H01B), C019(H01C,
 H01D), C01F(H01I,H01J), C01I(H01K,H01L), C01J(H01M,H01N), C01K(H01O,H01P),
 C01L(H01Q,H01R), C01O(H01W,H01X), C01Q(H01Z,HB), C01T(H0AA,HE), C01U(H1AA,HF),
 C01Z(H6AA,HO), C022(H02D,H02E), C023(H02F,H02G), C027(H02N,H02O), C2(H2A,H2B),
 C4(H4A,H4B)
5.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00M(H00M), C00P(H00P), C00X(H00X), C012(H012),
 C016(H016), C01A(H01E), C01B(H01F), C01D(H01G), C01E(H01H), C01M(H01S)
5.d Idealised Me refined as rotating group:
 C01N(H01T,H01U,H01V), C01P(H01Y,H,HA), C01S(H01,HC,HD), C01V(H2AA,HG,HH),
 C01W(H3AA,HI,HJ), C01X(H4AA,HK,HL), C01Y(H5AA,HM,HN), C020(H02A,H02B,H02C),
 C025(H02H,H02I,H02J), C026(H02K,H02L,H02M), C028(H02P,H02Q,H02R), C1(H1A,H1B,
 H1C), C3(H3A,H3B,H3C), C1AA(H1AB,H1AC,H1AD), C0AA(H0AB,H0AC,H0AD), C11(H11A,
 H11B,H11C)
;
_shelx_res_checksum              98401
_shelx_hkl_checksum              13642
_olex2_submission_special_instructions 'No special instructions were received'