High-affinity single and double helical pseudofoldaxanes with cationic guests.
Zhong, Yulong; Sobiech, Thomas A.; Kauffmann, Brice; Song, Bo; Li, Xiaopeng; Ferrand, Yann; Huc, Ivan; Gong, Bing; Chemical science 14 (2023) 4759–4768; doi:10.1039/d3sc00524k

data_1568763
_publ_section_title
;
 High-affinity single and double helical pseudofoldaxanes with cationic
 guests.
;
_journal_issue                   18
_journal_name_full               'Chemical science'
_journal_page_first              4759
_journal_page_last               4768
_journal_paper_doi               10.1039/d3sc00524k
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety
'8(F6 P), 2(C124 H162 N8 O34.5), 2(C124 H151 N8 O35), 4.039(C25.5 H41 N2)'
_chemical_formula_sum            'C599 H792 F48 N40 O139 P8'
_chemical_formula_weight         11936.44
_chemical_properties_physical    Air-sensitive
_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             2021-08-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.12.01 svn.r5f60950 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-13 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.072(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   27.6163(5)
_cell_length_b                   45.0146(5)
_cell_length_c                   28.5060(4)
_cell_measurement_reflns_used    28225
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      58.3350
_cell_measurement_theta_min      3.2750
_cell_volume                     32839.8(10)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            146992
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        61.792
_diffrn_reflns_theta_max         61.792
_diffrn_reflns_theta_min         3.286
_diffrn_source                   'rotating anode Rigaku FRX'
_exptl_absorpt_coefficient_mu    0.965
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60788
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       bloc
_exptl_crystal_F_000             12660
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.278
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.726
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     3920
_refine_ls_number_reflns         50210
_refine_ls_number_restraints     3182
_refine_ls_restrained_S_all      1.809
_refine_ls_R_factor_all          0.1605
_refine_ls_R_factor_gt           0.1342
_refine_ls_shift/su_max          2.028
_refine_ls_shift/su_mean         0.019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4000
_refine_ls_wR_factor_ref         0.4258
_reflns_Friedel_coverage         0.000
_reflns_number_gt                34012
_reflns_number_total             50210
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00524k2.cif
_cod_data_source_block           x2
_cod_depositor_comments
'Adding full bibliography for 1568763--1568764.cif.'
_cod_original_cell_volume        32839.8(9)
_cod_database_code               1568763
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Restrained distances
 C4BA-C124
 1.54 with sigma of 0.02
 C41-C290
 1.54 with sigma of 0.02
 C84-C5CA
 1.54 with sigma of 0.02
 C5AA-C5BA
 1.54 with sigma of 0.02
 C4AA-C3AA = C3AA-C161
 1.54 with sigma of 0.02
 C4AA-C161
 2.8 with sigma of 0.02
 C68-C2AA = C2CA-C2AA
 1.54 with sigma of 0.02
 C7AA-C6AA = C8AA-C7AA
 1.54 with sigma of 0.02
 C6AA-C331 = C8CA-C331 = C8CA-C0BA
 1.54 with sigma of 0.02
 C6AA-C19
 1.54 with sigma of 0.02
 C4BA-C124 = C1BA-C124
 1.54 with sigma of 0.02
 C331-C19
 1.54 with sigma of 0.02
 C68-C2AA
 2.8 with sigma of 0.02
 C1DA-C5CA
 2.8 with sigma of 0.02
 C37-C2BA = C61-C37 = C54-C37 = C54-C36
 1.5 with sigma of 0.02
 C52-C10 = C52-C3BA = C52-C0CA
 1.5 with sigma of 0.02
 C7CA-C1AA = C2DA-C1AA = C1AA-C10
 1.5 with sigma of 0.02
 C7CA-C2DA
 2.8 with sigma of 0.02
 C3DA-C0BA
 1.54 with sigma of 0.02
 C4CA-C0AA
 1.54 with sigma of 0.02
 C65-C43
 1.54 with sigma of 0.02
 C2CA-C2AA = C68-C2CA = C68-C42
 1.54 with sigma of 0.02
 C84-C65 = C84-C5CA
 1.54 with sigma of 0.02
 C5AA-C50
 1.54 with sigma of 0.02
 C50-C31 = C5BA-C5AA
 1.54 with sigma of 0.02
2. Rigid body (RIGU) restrains
 N192, C326, C9, C19, C6AA, C331, C8CA, C0BA, C7AA, C8AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C5CA, C84, C65, C43, O283
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C2CA, C2AA, C42, C68, O269
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C2BA, C37, C61, C54, C36, O299, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7CA, C2DA, C1AA, C10, C295, O128
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C0CA, C3BA, C52, C10, C295
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C5CA, C84, C65
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
3. Others
 Fixed Sof: C331(0.5) H33H(0.5) H33I(0.5) H10A(0.5) H10B(0.5) H10C(0.5)
 H10D(0.5) H19C(0.5) H19D(0.5) H19E(0.5) H19F(0.5) C35(0.5) H35(0.5) C41(0.5)
 H41A(0.5) H41B(0.5) O49(0.5) C52(0.5) C58(0.5) H58A(0.5) H58B(0.5) H58C(0.5)
 C67(0.5) H67A(0.5) H67B(0.5) C110(0.5) H11A(0.5) H11B(0.5) H11C(0.5) C7AA(0.5)
 H7AA(0.5) H7AB(0.5) C8AA(0.5) H8AA(0.5) H8AB(0.5) C3BA(0.5) H3BA(0.5)
 H3BB(0.5) H3BC(0.5) C6AA(0.5) H6AA(0.5) H6AB(0.5) C7BA(0.5) H7BA(0.5)
 H7BB(0.5) C9AA(0.5) H9AA(0.5) H9AB(0.5) C0BA(0.5) H0BA(0.5) H0BB(0.5)
 C124(0.5) H12A(0.5) H12B(0.5) C0CA(0.5) H0CA(0.5) H0CB(0.5) H0CC(0.5)
 C8CA(0.5) H8CA(0.5) H8CB(0.5) C1BA(0.5) H1BA(0.5) H1BB(0.5) H1BC(0.5) C1(0.5)
 H1A(0.5) H1B(0.5) H1C(0.5) C0DA(0.5) H0DA(0.5) H0DB(0.5) C1DA(0.5) H1DA(0.5)
 H1DB(0.5) H1DC(0.5) C1AA(0.5) H1AA(0.5) C2DA(0.5) H2DA(0.5) H2DB(0.5)
 H2DC(0.5) C7CA(0.5) H7CA(0.5) H7CB(0.5) H7CC(0.5) C3DA(0.5) H3DA(0.5)
 H3DB(0.5) H3DC(0.5)
4.a Ternary CH refined with riding coordinates:
 C309(H309), C22(H22), C4(H4), C16(H16), C21(H21), C35(H35), C37(H37),
 C53(H53), C62(H62), C71(H71), C3AA(H3AA), C1AA(H1AA)
4.b Secondary CH2 refined with riding coordinates:
 C083(H08A,H08B), C142(H14A,H14B), C179(H17A,H17B), C181(H18A,H18B), C193(H19A,
 H19B), C200(H20A,H20B), C211(H21A,H21B), C212(H21C,H21D), C219(H21H,H21I),
 C223(H22C,H22D), C228(H22A,H22B), C231(H23A,H23B), C234(H23C,H23D), C235(H23J,
 H23K), C238(H23H,H23I), C247(H24A,H24B), C253(H25M,H25N), C255(H25O,H25P),
 C263(H26A,H26B), C267(H26K,H26L), C268(H26M,H26N), C271(H27F,H27G), C276(H27H,
 H27I), C277(H27J,H27K), C279(H27A,H27B), C281(H28A,H28B), C282(H28C,H28D),
 C284(H28H,H28I), C290(H29A,H29B), C291(H29K,H29L), C295(H29F,H29G), C300(H30F,
 H30G), C301(H30J,H30K), C305(H30H,H30I), C308(H30D,H30E), C310(H31J,H31K),
 C311(H31A,H31B), C314(H31L,H31M), C315(H31N,H31O), C316(H31F,H31G), C317(H31H,
 H31I), C318(H31P,H31Q), C320(H32C,H32D), C321(H32E,H32F), C322(H32G,H32H),
 C325(H32M,H32N), C326(H32K,H32L), C327(H32A,H32B), C328(H32I,H32J), C330(H33F,
 H33G), C331(H33H,H33I), C332(H33A,H33B), C334(H33J,H33K), C3(H3A,H3B), C5(H5A,
 H5B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C10(H10C,H10D),
 C11(H11D,H11E), C12(H12C,H12D), C14(H14C,H14D), C17(H17C,H17D), C18(H18C,H18D),
  C19(H19C,H19D), C19(H19E,H19F), C24(H24F,H24G), C26(H26F,H26G), C28(H28M,
 H28N), C31(H31R,H31S), C32(H32O,H32P), C36(H36A,H36B), C38(H38A,H38B),
 C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B),
  C50(H50A,H50B), C54(H54A,H54B), C55(H55A,H55B), C57(H57A,H57B), C65(H65A,
 H65B), C67(H67A,H67B), C68(H68A,H68B), C84(H84A,H84B), C5AA(H5AA,H5AB),
 C7AA(H7AA,H7AB), C8AA(H8AA,H8AB), C6AA(H6AA,H6AB), C0AA(H0AA,H0AB), C7BA(H7BA,
 H7BB), C9AA(H9AA,H9AB), C0BA(H0BA,H0BB), C8BA(H8BA,H8BB), C124(H12A,H12B),
 C8CA(H8CA,H8CB), C0DA(H0DA,H0DB)
4.c Aromatic/amide H refined with riding coordinates:
 N019(H019), N020(H020), N023(H023), N025(H025), N048(H048), N050(H050),
 N051(H051), N056(H056), N073(H073), N084(H084), C085(H085), N086(H086),
 C087(H087), N090(H090), C094(H094), N102(H102), C103(H103), C104(H104),
 N112(H112), C115(H115), C125(H125), C129(H129), C138(H138), C143(H143),
 C144(H144), C145(H145), C148(H148), C149(H149), C152(H152), C156(H156),
 C157(H157), C158(H158), C174(H174), C175(H175), C176(H176), C178(H178),
 C185(H185), C186(H186), C187(H187), C195(H195), C196(H196), C201(H201),
 C206(H206), C209(H209), C213(H213), C214(H214), C216(H216), C220(H220),
 C221(H221), N225(H225), C230(H230), C232(H232), C236(H236), C237(H237),
 C240(H240), C241(H241), C244(H244), C248(H248), C252(H252), C254(H254),
 C273(H273), C296(H296), C297(H297), C298(H298), C303(H303), C304(H304),
 C313(H313), C319(H319), C329(H329), C13(H13), C30(H30)
4.d Idealised Me refined as rotating group:
 C173(H17E,H17F,H17G), C215(H21J,H21K,H21L), C217(H21E,H21F,H21G), C239(H23E,
 H23F,H23G), C249(H24C,H24D,H24E), C250(H25G,H25H,H25I), C251(H25J,H25K,H25L),
 C257(H25A,H25B,H25C), C260(H26H,H26I,H26J), C264(H26C,H26D,H26E), C285(H28J,
 H28K,H28L), C289(H28E,H28F,H28G), C292(H29H,H29I,H29J), C294(H29C,H29D,H29E),
 C302(H30A,H30B,H30C), C312(H31C,H31D,H31E), C335(H33C,H33D,H33E), C2(H2A,H2B,
 H2C), C6(H6A,H6B,H6C), C15(H15A,H15B,H15C), C20(H20C,H20D,H20E), C25(H25D,H25E,
 H25F), C27(H27C,H27D,H27E), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C51(H51A,
 H51B,H51C), C58(H58A,H58B,H58C), C61(H61A,H61B,H61C), C63(H63A,H63B,H63C),
 C89(H89A,H89B,H89C), C91(H91A,H91B,H91C), C110(H11A,H11B,H11C), C2BA(H2BA,H2BB,
 H2BC), C3BA(H3BA,H3BB,H3BC), C4AA(H4AA,H4AB,H4AC), C161(H16A,H16B,H16C),
 C1CA(H1CA,H1CB,H1CC), C9BA(H9BA,H9BB,H9BC), C3CA(H3CA,H3CB,H3CC), C56(H56A,
 H56B,H56C), C95(H95A,H95B,H95C), C5BA(H5BA,H5BB,H5BC), C0CA(H0CA,H0CB,H0CC),
 C1BA(H1BA,H1BB,H1BC), C1(H1A,H1B,H1C), C1DA(H1DA,H1DB,H1DC), C2DA(H2DA,H2DB,
 H2DC), C7CA(H7CA,H7CB,H7CC), C3DA(H3DA,H3DB,H3DC)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              20712
_shelx_fab_checksum              33752
_olex2_submission_special_instructions 'No special instructions were received'