Tuning the porosity of triangular supramolecular adsorbents for superior haloalkane isomer separations
Hua, Bin; Ding, Yanjun; Alimi, Lukman O.; Moosa, Basem; Zhang, Gengwu; Baslyman, Walaa S.; Sessler, Jonathan; Khashab, Niveen M.; Chemical Science  (2021) –; doi:10.1039/D1SC03509F

data_1564600
_publ_section_title
;
 Tuning the porosity of triangular supramolecular adsorbents for superior
 haloalkane isomer separations
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03509F
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         '0.5(C4 H9 Cl), C45 H60 N6'
_chemical_formula_sum            'C47 H64.5 Cl0.5 N6'
_chemical_formula_weight         731.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-18 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8982(5)
_cell_length_b                   41.8156(12)
_cell_length_c                   5.6166(2)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.39
_cell_measurement_theta_min      2.69
_cell_volume                     4203.6(2)
_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      120.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            21071
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        66.579
_diffrn_reflns_theta_max         66.579
_diffrn_reflns_theta_min         2.685
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_description       block
_exptl_crystal_F_000             1588
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2381 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     764
_refine_ls_number_reflns         7304
_refine_ls_number_restraints     1100
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0616
_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^)+(0.0644P)^2^+1.7815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1612
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                6487
_reflns_number_total             7304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03509f2.cif
_cod_data_source_block           s
_cod_original_formula_sum        'C47 H64.50 Cl0.50 N6'
_cod_database_code               1564600
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.910
_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
2. Restrained distances
 C16A-C20A
 2.515 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
N3 \\sim N4 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14
\\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22
\\sim C23 \\sim C24 \\sim C29 \\sim C28 \\sim C27 \\sim C26 \\sim C25 \\sim C30
\\sim C37 \\sim N5 \\sim N6 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35
\\sim C36: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
N3A \\sim N4A \\sim N5A \\sim C8A \\sim C9A \\sim C14A \\sim C13A \\sim C12A
\\sim C11A \\sim C10A \\sim C15A \\sim C16A \\sim C17A \\sim C18A \\sim C19A
\\sim C20A \\sim C21A \\sim C22A \\sim C23A \\sim C24A \\sim C29A \\sim C28A
\\sim C27A \\sim C26A \\sim C25A \\sim C30A \\sim C31A \\sim C35A \\sim C36A
\\sim C37A \\sim N6A \\sim C32A \\sim C33A \\sim C34A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
Cl1 \\sim C46 \\sim C47 \\sim C48 \\sim C49: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 N3, N4, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21,
 C22, C23, C24, C29, C28, C27, C26, C25, C37, N5, N6, C30, C31, C32, C33, C34,
 C35, C36, C38, N2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N3A, N4A, N5A, C8A, C9A, C14A, C13A, C12A, C11A, C10A, C15A, C16A, C17A, C18A,
  C19A, C20A, C21A, C22A, C23A, C24A, C29A, C28A, C27A, C26A, C25A, C30A, C37A,
 N6A, C31A, C32A, C33A, C34A, C35A, C36A, C38
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 Cl1, C46, C47, C48, C49
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(N3A)=Sof(N4A)=Sof(N5A)=Sof(N6A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)=
 Sof(C14A)=Sof(H14A)=Sof(C13A)=Sof(H13A)=Sof(C12A)=Sof(C11A)=Sof(H11A)=
 Sof(C10A)=Sof(H10A)=Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16A)=
 Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18C)=Sof(H18D)=Sof(C19A)=Sof(H19C)=
 Sof(H19D)=Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C21A)=Sof(H21C)=Sof(H21D)=
 Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(C24A)=
 Sof(C29A)=Sof(H29A)=Sof(C28A)=Sof(H28A)=Sof(C27A)=Sof(C26A)=Sof(H26A)=
 Sof(C25A)=Sof(H25A)=Sof(C30A)=Sof(H30C)=Sof(H30D)=Sof(C31A)=Sof(H31A)=
 Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33C)=Sof(H33D)=Sof(C34A)=Sof(H34C)=
 Sof(H34D)=Sof(C35A)=Sof(H35C)=Sof(H35D)=Sof(C36A)=Sof(H36C)=Sof(H36D)=
 Sof(C37A)=Sof(H37C)=Sof(H37D)=Sof(H38C)=Sof(H38D)=1-FVAR(1)
 Sof(N3)=Sof(N4)=Sof(N5)=Sof(N6)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C9)=Sof(C10)=
 Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=
 Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=
 Sof(H23B)=Sof(C24)=Sof(C29)=Sof(H29)=Sof(C28)=Sof(H28)=Sof(C27)=Sof(C26)=
 Sof(H26)=Sof(C25)=Sof(H25)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31)=
 Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C34)=Sof(H34A)=Sof(H34B)=
 Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C37)=Sof(H37A)=
 Sof(H37B)=Sof(H38A)=Sof(H38B)=FVAR(1)
 Fixed Sof: Cl1(0.5) C46(0.5) H46A(0.5) H46B(0.5) C47(0.5) H47A(0.5) H47B(0.5)
 C48(0.5) H48A(0.5) H48B(0.5) C49(0.5) H49A(0.5) H49B(0.5) H49C(0.5)
6.a Riding coordinates:
 C49(H49A,H49B,H49C)
6.b Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C16(H16), C16A(H16A), C17(H17), C17A(H17A), C31(H31),
 C31A(H31A), C32(H32), C32A(H32A)
6.c Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C3(H3A,H3B), C4(H4A,H4B),
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C8A(H8AA,H8AB), C15(H15A,
 H15B), C15A(H15C,H15D), C18(H18A,H18B), C18A(H18C,H18D), C19(H19A,H19B),
 C19A(H19C,H19D), C20(H20A,H20B), C20A(H20C,H20D), C21(H21A,H21B), C21A(H21C,
 H21D), C22(H22A,H22B), C22A(H22C,H22D), C23(H23A,H23B), C23A(H23C,H23D),
 C30(H30A,H30B), C30A(H30C,H30D), C33(H33A,H33B), C33A(H33C,H33D), C34(H34A,
 H34B), C34A(H34C,H34D), C35(H35A,H35B), C35A(H35C,H35D), C36(H36A,H36B),
 C36A(H36C,H36D), C37(H37A,H37B), C37A(H37C,H37D), C38(H38A,H38B), C38(H38C,
 H38D), C45(H45A,H45B)
6.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C14A(H14A), C13A(H13A), C11A(H11A),
 C10A(H10A), C29(H29), C28(H28), C26(H26), C25(H25), C29A(H29A), C28A(H28A),
 C26A(H26A), C25A(H25A), C40(H40), C41(H41), C43(H43), C44(H44)
6.e Fitted hexagon refined as free rotating group:
 C9(C10,C11,C12,C13,C14), C9A(C14A,C13A,C12A,C11A,C10A), C24(C29,C28,C27,C26,
 C25), C24A(C29A,C28A,C27A,C26A,C25A)
;
_shelx_res_checksum              28025
_shelx_hkl_checksum              35053
_olex2_submission_special_instructions 'No special instructions were received'