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_1564601
_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         '1(C4 H9 Cl1), C45 H60 N6'
_chemical_formula_sum            'C49 H69 Cl N6'
_chemical_formula_weight         777.55
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2020-10-23
_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                107.383(7)
_cell_angle_beta                 104.681(8)
_cell_angle_gamma                104.350(7)
_cell_formula_units_Z            2
_cell_length_a                   10.9057(15)
_cell_length_b                   14.2504(17)
_cell_length_c                   16.844(2)
_cell_measurement_reflns_used    9825
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      26.367
_cell_measurement_theta_min      2.579
_cell_volume                     2263.3(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            82923
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.061
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0702 before and 0.0481 after correction. The Ratio of minimum to maximum transmission is 0.9632. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_description       block
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.747
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 8024 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.100(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1157
_refine_ls_number_reflns         18192
_refine_ls_number_restraints     618
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0914P)^2^+0.7378P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1423
_reflns_Friedel_coverage         0.975
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                17213
_reflns_number_total             18192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03509f2.cif
_cod_data_source_block           pta_2cb_0m
_cod_original_cell_volume        2263.4(5)
_cod_database_code               1564601
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.985
_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
 Cl2-C97
 1.79 with sigma of 0.02
 C93-C97 = C97-C95
 1.54 with sigma of 0.02
 C97-C95 = C95-C94
 1.54 with sigma of 0.02
 C103-C104 = C104-C105
 1.54 with sigma of 0.02
 C104-C105 = C105-C106
 1.54 with sigma of 0.02
 Cl4-C105
 1.79 with sigma of 0.02
 C105-C104 = C104-C103
 1.54 with sigma of 0.02
 C91-C96 = C96-C98
 1.54 with sigma of 0.02
 C96-C98 = C98-C92
 1.54 with sigma of 0.02
 Cl1-C96
 1.79 with sigma of 0.02
 C101-C100 = C100-C99
 1.54 with sigma of 0.02
 C99-C100 = C100-C101
 1.54 with sigma of 0.02
 C1-C101 = C101-C100
 1.54 with sigma of 0.02
 C92-C101 = C101-C100
 1.54 with sigma of 0.02
 C101-C100 = C100-C91
 1.54 with sigma of 0.02
 Cl3B-C101
 1.79 with sigma of 0.02
 C1B-C2AA = C2AA-C1AA
 1.54 with sigma of 0.02
 C2AA-C1AA = C1AA-C0AA
 1.54 with sigma of 0.02
 Cl3A-C2AA
 1.79 with sigma of 0.02
 Cl2-C93
 2.723 with sigma of 0.04
 Cl2-C95
 2.723 with sigma of 0.04
 C93-C95
 2.515 with sigma of 0.04
 C97-C94
 2.515 with sigma of 0.04
 C103-C105
 2.515 with sigma of 0.04
 C105-C103
 2.515 with sigma of 0.04
 Cl4-C106
 2.723 with sigma of 0.04
 C104-C106
 2.515 with sigma of 0.04
 Cl4-C104
 2.723 with sigma of 0.001
 C101-C99
 2.515 with sigma of 0.04
 C91-C98
 2.515 with sigma of 0.04
 C96-C92
 2.515 with sigma of 0.04
 Cl1-C91
 2.723 with sigma of 0.04
 Cl1-C98
 2.723 with sigma of 0.04
 C99-C101
 2.515 with sigma of 0.04
 C1-C100
 2.515 with sigma of 0.04
 Cl3B-C1
 2.723 with sigma of 0.001
 C92-C100
 2.515 with sigma of 0.04
 C101-C91
 2.515 with sigma of 0.04
 Cl3B-C100
 2.723 with sigma of 0.04
 Cl3B-C92
 2.723 with sigma of 0.04
 C1B-C1AA
 2.515 with sigma of 0.04
 C2AA-C0AA
 2.515 with sigma of 0.04
 Cl3A-C1B
 2.723 with sigma of 0.04
 Cl3A-C1AA
 2.723 with sigma of 0.04
 Cl2-C94 \\sim Cl4-C103
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl2 \\sim C93 \\sim C94 \\sim C95 \\sim C97 \\sim Cl4 \\sim C103 \\sim C104
\\sim C105 \\sim C106: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Cl1 \\sim C91 \\sim C92 \\sim C96 \\sim C98 \\sim Cl3B \\sim C99 \\sim C100
\\sim C101 \\sim C1: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02
C96 \\sim Cl1 \\sim C98 \\sim C99 \\sim C1 \\sim C101 \\sim C91 \\sim C100
\\sim C92 \\sim Cl3B \\sim C2AA \\sim Cl3A \\sim C1AA \\sim C1B \\sim C0AA:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl3A) \\sim Ueq, Uanis(C2AA) \\sim Ueq, Uanis(Cl1) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
Uanis(C98) \\sim Ueq, Uanis(C93) \\sim Ueq, Uanis(C99) \\sim Ueq, Uanis(C0AA)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 Cl2, C93, C94, C95, C97
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 Cl4, C103, C104, C105, C106
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 Cl1, C91, C92, C96, C98
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 Cl3B, C99, C100, C101, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C101, C91, C100, C92, Cl3B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C96, Cl1, C98, C99, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C2AA, Cl3A, C1AA, C1B, C0AA
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 1*[Sof(Cl1)+Sof(C96)+Sof(H96)+Sof(C98)+Sof(H98A)+Sof(H98B)+Sof(C99)+Sof(H99A)+
 Sof(H99B)+Sof(H99C)+Sof(C1)+Sof(H1A)+Sof(H1B)+Sof(H1C)]+1*[Sof(C91)+Sof(H91A)+
 Sof(H91B)+Sof(H91C)+Sof(C92)+Sof(H92A)+Sof(H92B)+Sof(H92C)+Sof(Cl2)+Sof(C93)+
 Sof(H93A)+Sof(H93B)+Sof(H93C)+Sof(C94)+Sof(H94A)+Sof(H94B)+Sof(H94C)+Sof(C95)+
 Sof(H95A)+Sof(H95B)+Sof(C97)+Sof(H97)+Sof(Cl3B)+Sof(C100)+Sof(H10A)+Sof(H10B)+
 Sof(C101)+Sof(H101)+Sof(Cl4)+Sof(C103)+Sof(H10C)+Sof(H10D)+Sof(H10E)+Sof(C104)+
 Sof(H10F)+Sof(H10G)+Sof(C105)+Sof(H105)+Sof(C106)+Sof(H10H)+Sof(H10I)+
 Sof(H10J)]+1*[Sof(C2AA)+Sof(H2AA)+Sof(C0AA)+Sof(H0AA)+Sof(H0AB)+Sof(H0AC)+
 Sof(C1AA)+Sof(H1AA)+Sof(H1AB)+Sof(C1B)+Sof(H1BA)+Sof(H1BB)+Sof(H1BC)+
 Sof(Cl3A)]=1 with esd of 0.0001
 Sof(Cl1)=Sof(C96)=Sof(H96)=Sof(C98)=Sof(H98A)=Sof(H98B)=Sof(C99)=Sof(H99A)=
 Sof(H99B)=Sof(H99C)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(1)
 Sof(Cl4)=Sof(C103)=Sof(H10C)=Sof(H10D)=Sof(H10E)=Sof(C104)=Sof(H10F)=
 Sof(H10G)=Sof(C105)=Sof(H105)=Sof(C106)=Sof(H10H)=Sof(H10I)=Sof(H10J)=1-FVAR(2)
 Sof(C91)=Sof(H91A)=Sof(H91B)=Sof(H91C)=Sof(C92)=Sof(H92A)=Sof(H92B)=Sof(H92C)=
 Sof(Cl2)=Sof(C93)=Sof(H93A)=Sof(H93B)=Sof(H93C)=Sof(C94)=Sof(H94A)=Sof(H94B)=
 Sof(H94C)=Sof(C95)=Sof(H95A)=Sof(H95B)=Sof(C97)=Sof(H97)=Sof(Cl3B)=Sof(C100)=
 Sof(H10A)=Sof(H10B)=Sof(C101)=Sof(H101)=FVAR(2)
 Sof(C2AA)=Sof(H2AA)=Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(H0AC)=Sof(C1AA)=
 Sof(H1AA)=Sof(H1AB)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(Cl3A)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C96(H96), C97(H97), C101(H101), C105(H105), C16(H16), C21(H21), C37(H37),
 C49(H49), C51(H51), C53(H53), C25(H25), C36(H36), C45(H45), C52(H52), C58(H58),
  C71(H71), C2AA(H2AA)
6.b Secondary CH2 refined with riding coordinates:
 C98(H98A,H98B), C95(H95A,H95B), C100(H10A,H10B), C104(H10F,H10G), C18(H18A,
 H18B), C22(H22A,H22B), C27(H27A,H27B), C30(H30A,H30B), C32(H32A,H32B),
 C35(H35A,H35B), C39(H39A,H39B), C48(H48A,H48B), C50(H50A,H50B), C57(H57A,H57B),
  C59(H59A,H59B), C60(H60A,H60B), C63(H63A,H63B), C64(H64A,H64B), C72(H72A,
 H72B), C75(H75A,H75B), C81(H81A,H81B), C82(H82A,H82B), C85(H85A,H85B),
 C86(H86A,H86B), C88(H88A,H88B), C6(H6A,H6B), C8(H8A,H8B), C12(H12A,H12B),
 C23(H23A,H23B), C40(H40A,H40B), C44(H44A,H44B), C55(H55A,H55B), C61(H61A,H61B),
  C62(H62A,H62B), C65(H65A,H65B), C66(H66A,H66B), C68(H68A,H68B), C69(H69A,
 H69B), C73(H73A,H73B), C77(H77A,H77B), C78(H78A,H78B), C79(H79A,H79B),
 C83(H83A,H83B), C87(H87A,H87B), C89(H89A,H89B), C90(H90A,H90B), C1AA(H1AA,H1AB)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C10(H10), C15(H15), C17(H17), C28(H28), C29(H29), C38(H38),
 C41(H41), C42(H42), C54(H54), C56(H56), C4(H4), C14(H14), C19(H19), C33(H33),
 C34(H34), C43(H43), C67(H67), C70(H70), C74(H74), C76(H76), C80(H80), C84(H84)
6.d Idealised Me refined as rotating group:
 C91(H91A,H91B,H91C), C92(H92A,H92B,H92C), C93(H93A,H93B,H93C), C94(H94A,H94B,
 H94C), C99(H99A,H99B,H99C), C1(H1A,H1B,H1C), C103(H10C,H10D,H10E), C106(H10H,
 H10I,H10J), C0AA(H0AA,H0AB,H0AC), C1B(H1BA,H1BB,H1BC)
;
_shelx_res_checksum              52865
_shelx_hkl_checksum              32752
_olex2_submission_special_instructions 'No special instructions were received'