Adsorptive separation of para-xylene by nonporous adaptive crystals of phenanthrene[2]arene
Hou, Ying; Duan, Yin-Rong; Ding, Man-Hua; Tang, Lin-Li; Zeng, Fei; RSC Advances 12 (2022) 22060–22063; doi:10.1039/D2RA03773D

data_7245287
_publ_section_title
;
 Adsorptive separation of para-xylene by nonporous adaptive crystals of
 phenanthrene[2]arene
;
_journal_issue                   34
_journal_name_full               'RSC Advances'
_journal_page_first              22060
_journal_page_last               22063
_journal_paper_doi               10.1039/D2RA03773D
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C66 H60 O12, C8 H10'
_chemical_formula_sum            'C74 H70 O12'
_chemical_formula_weight         1151.30
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-22
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-04-09 deposited with the CCDC.	2022-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.502(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.047(4)
_cell_length_b                   8.2362(19)
_cell_length_c                   26.661(6)
_cell_measurement_reflns_used    9125
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.43
_cell_volume                     3198.8(13)
_computing_data_collection       'Bruker SMART APEX II diffractrometer'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            34096
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         1.423
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         7226
_refine_ls_number_restraints     850
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0627
_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^)+(0.1176P)^2^+0.5847P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.2054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4827
_reflns_number_total             7226
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra03773d2.cif
_cod_data_source_block           22022501_0m_a
_cod_original_cell_volume        3198.7(13)
_cod_database_code               7245287
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.990
_exptl_crystal_mounting_method
'The title complex was mounted in a sealed capillary.'
_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
 C40-C34 = C41-C37
 1.5 with sigma of 0.01
 O5A-C26A \\sim O5-C26
 with sigma of 0.02
 C26A-C31A \\sim C26-C31
 with sigma of 0.02
 C40-C39 \\sim C40-C35
 with sigma of 0.02
 C41-C36 \\sim C41-C38
 with sigma of 0.02
 C26-C25 \\sim C26A-C25
 with sigma of 0.02
 O5-C31 \\sim O5A-C31A
 with sigma of 0.02
 C30A-C29A \\sim C30-C29
 with sigma of 0.02
 C30-C25 \\sim C30A-C25
 with sigma of 0.02
 O6-C32 \\sim O6A-C32A
 with sigma of 0.02
 C29-C28 \\sim C29A-C28
 with sigma of 0.02
 C32-C29 \\sim C32A-C29A
 with sigma of 0.02
 C28-C27 \\sim C28-C27A
 with sigma of 0.02
 O6-C29 \\sim O6A-C29A
 with sigma of 0.02
 O4-C21 \\sim O4A-C21A
 with sigma of 0.02
 C22A-C17 \\sim C22-C17
 with sigma of 0.02
 O4-C24 \\sim O4A-C24A
 with sigma of 0.02
 C24-C21 \\sim C24A-C21A
 with sigma of 0.02
 C22A-C21A \\sim C22-C21
 with sigma of 0.02
 O3-C23 \\sim O3A-C23A
 with sigma of 0.02
 C21A-C20 \\sim C21-C20
 with sigma of 0.02
 C19-C18 \\sim C19A-C18A
 with sigma of 0.02
 O3-C18 \\sim O3A-C18A
 with sigma of 0.02
 C20-C19 \\sim C20-C19A
 with sigma of 0.02
 C18-C23 \\sim C18A-C23A
 with sigma of 0.02
 C18-C17 \\sim C18A-C17
 with sigma of 0.02
3. Restrained planarity
 C29A, C30A, C25, C26A, C27A, C28, O6A, O5A
 with sigma of 0.1
 C39, C34, C40, C35, C38, C36, C37, C41
 with sigma of 0.1
 C28, C29, C30, C25, C26, C27, O5, O6
 with sigma of 0.1
 C19A, C18A, C17, C22A, C20, C21A, O4A, O3A
 with sigma of 0.1
 O3, C18, C17, C22, C21, C20, C19, O4
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
O5 \\sim C27 \\sim C31 \\sim O5A \\sim C26A \\sim C27A \\sim C31A \\sim C26
\\sim O6 \\sim C32 \\sim O6A \\sim C32A \\sim C29 \\sim C30 \\sim C29A \\sim
C30A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
C34 \\sim C39 \\sim C35 \\sim C40 \\sim C38 \\sim C36 \\sim C37 \\sim C41:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
O4 \\sim C21 \\sim C22 \\sim C24 \\sim O4A \\sim C21A \\sim C22A \\sim C24A
\\sim O3 \\sim C18 \\sim C19 \\sim C23 \\sim O3A \\sim C18A \\sim C19A \\sim
C23A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
Uanis(C40) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C35)
\\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C37) \\sim Ueq,
Uanis(C41) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C37, C34, C40, C39, C35, C38, C36, C41
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O5A, C28, C32A, C29A, C26A, C31A, C27A, O6A, C25, C30A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O5, C29, C31, O6, C30, C26, C32, C27, C25, C28
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C17, C22, C21, C20, C19, C18, C24, O4, O3, C23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C23A, O3A, C18A, C17, C22A, C21A, C20, C19A, O4A, C24A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Sof(O5A)=Sof(O6A)=Sof(C26A)=Sof(C27A)=Sof(H27A)=Sof(C29A)=Sof(C30A)=Sof(H30A)=
 Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=Sof(C32A)=Sof(H32D)=Sof(H32E)=
 Sof(H32F)=1-FVAR(1)
 Sof(O5)=Sof(O6)=Sof(C26)=Sof(C27)=Sof(H27)=Sof(C29)=Sof(C30)=Sof(H30)=
 Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=
 FVAR(1)
 Sof(O3A)=Sof(O4A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C21A)=Sof(C22A)=Sof(H22A)=
 Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(C24A)=Sof(H24D)=Sof(H24E)=
 Sof(H24F)=1-FVAR(2)
 Sof(O3)=Sof(O4)=Sof(C18)=Sof(C19)=Sof(H19)=Sof(C21)=Sof(C22)=Sof(H22)=
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=
 FVAR(2)
 Fixed Sof: C34(0.5) C39(0.5) H39(0.5) C38(0.5) H38(0.5) C37(0.5) C36(0.5)
 H36(0.5) C35(0.5) H35(0.5) C40(0.5) H40A(0.5) H40B(0.5) H40C(0.5) C41(0.5)
 H41A(0.5) H41B(0.5) H41C(0.5)
 Fixed X: C26A(0.84472)
7.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C9(H9), C11(H11), C12(H12), C19(H19), C22(H22),
 C27(H27), C30(H30), C39(H39), C38(H38), C36(H36), C35(H35), C27A(H27A),
 C30A(H30A), C19A(H19A), C22A(H22A)
7.c Fitted hexagon refined as free rotating group:
 C34(C39,C38,C37,C36,C35)
7.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C40(H40A,H40B,H40C), C41(H41A,
 H41B,H41C), C31A(H31D,H31E,H31F), C32A(H32D,H32E,H32F), C23A(H23D,H23E,H23F),
 C24A(H24D,H24E,H24F)
;
_shelx_res_checksum              55365
_olex2_submission_special_instructions 'No special instructions were received'