Photon-gated foldaxane assembly/disassembly.
Yao, Chenhao; Gole, Bappaditya; Bui, Anh Thy; Kauffmann, Brice; Huc, Ivan; McClenaghan, Nathan D.; Ferrand, Yann; Chemical communications (Cambridge, England) 60 (2024) 8415–8418; doi:10.1039/d4cc03218g

data_7133375
_publ_section_title
;
 Photon-gated foldaxane assembly/disassembly.
;
_journal_issue                   64
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8415
_journal_page_last               8418
_journal_paper_doi               10.1039/d4cc03218g
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety
'C268 H258 F10 N46 O42, C45 H51 N3 O4, C H Cl3, H2 O, [+ solvents]'
_chemical_formula_sum            'C314 H312 Cl3 F10 N49 O47'
_chemical_formula_weight         5820.46
_chemical_name_systematic        foldax
_chemical_properties_physical    Air-sensitive
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.12.01 svn.r5f60950 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-03-25 deposited with the CCDC.	2024-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                101.2045(15)
_cell_angle_beta                 91.4858(14)
_cell_angle_gamma                111.9064(18)
_cell_formula_units_Z            2
_cell_length_a                   23.7615(4)
_cell_length_b                   24.0825(4)
_cell_length_c                   35.9358(6)
_cell_measurement_reflns_used    33460
_cell_measurement_temperature    135
_cell_measurement_theta_max      50.8210
_cell_measurement_theta_min      2.8810
_cell_volume                     18605.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      135
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -77.00  89.00   1.00    2.00    --    0.00  46.00   0.00  166
  2  \w    -81.00  14.00   1.00    2.00    --    5.00  37.00 150.00   95
  3  \w   -107.00  26.00   1.00   30.00    --  -63.20  53.00 107.94  133
  4  \w   -152.00-121.00   1.00   30.00    --  -63.20  55.00 140.32   31
  5  \w   -106.00 -36.00   1.00   30.00    --  -63.20  55.00-129.02   70
  6  \w   -153.00 -17.00   1.00   30.00    --  -63.20  55.00-155.34  136
  7  \w   -149.00  10.00   1.00   30.00    --  -63.20  55.00  88.26  159
  8  \w   -148.00 -83.00   1.00   30.00    --  -63.20  55.00 -19.61   65
  9  \w   -153.00-121.00   1.00   30.00    --  -63.20  55.00  45.95   32
 10  \w   -152.00-100.00   1.00   30.00    --  -63.20  55.00 -53.19   52
 11  \w   -144.00  12.00   1.00   30.00    --  -63.20  55.00 148.41  156
 12  \w   -152.00 -84.00   1.00   30.00    --  -63.20  55.00  53.59   68
 13  \w   -152.00 -59.00   1.00   30.00    --  -63.20  55.00-107.00   93
 14  \w   -111.00 -30.00   1.00   30.00    --  -63.20  55.00 168.27   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku FRX'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0179555000
_diffrn_orient_matrix_UB_12      -0.0058257000
_diffrn_orient_matrix_UB_13      -0.0410370000
_diffrn_orient_matrix_UB_21      -0.0677777000
_diffrn_orient_matrix_UB_22      -0.0343275000
_diffrn_orient_matrix_UB_23      -0.0156894000
_diffrn_orient_matrix_UB_31      -0.0049792000
_diffrn_orient_matrix_UB_32      0.0615080000
_diffrn_orient_matrix_UB_33      -0.0015330000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            122926
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        51.389
_diffrn_reflns_theta_max         51.389
_diffrn_reflns_theta_min         2.867
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.039
_exptl_crystal_description       block
_exptl_crystal_F_000             6112
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.313
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     3853
_refine_ls_number_reflns         39846
_refine_ls_number_restraints     263
_refine_ls_restrained_S_all      1.325
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.1015
_refine_ls_shift/su_max          3.453
_refine_ls_shift/su_mean         0.037
_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          0.3192
_refine_ls_wR_factor_ref         0.3510
_reflns_Friedel_coverage         0.000
_reflns_number_gt                24229
_reflns_number_total             39846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03218g2.cif
_cod_data_source_block           fold
_cod_depositor_comments          'Adding full bibliography for 7133375.cif.'
_cod_original_cell_volume        18605.6(6)
_cod_database_code               7133375
_shelx_shelxl_version_number     2018/3
_cell_oxdiff_angle_alpha         101.2045(15)
_cell_oxdiff_angle_beta          91.4858(14)
_cell_oxdiff_angle_gamma         111.9064(18)
_cell_oxdiff_length_a            23.7615(4)
_cell_oxdiff_length_b            24.0825(4)
_cell_oxdiff_length_c            35.9358(6)
_cell_oxdiff_measurement_reflns_used 33460
_cell_oxdiff_volume              18605.6(6)
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.961
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     50.38
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C1GA-C15
 1.54 with sigma of 0.02
 C201-C0HA
 1.54 with sigma of 0.02
 C2FA-C253 = C7GA-C2FA = C7GA-C232 = C236-C232 = C253-C245 = C245-C236
 1.39 with sigma of 0.02
 C232-C0FA = C28-C0FA = C28-C249 = C249-C231 = C236-C231 = C243-C239 = C245-
 C243 = C239-C226 = C231-C226 = C251-C226 = C254-C251 = C254-C1FA = C249-C1FA
 1.39 with sigma of 0.02
 O38-C189
 1.25 with sigma of 0.02
 C80-C244 = C244-C240 = C8BA-C240 = C8BA-C135
 1.54 with sigma of 0.02
 C6-C1
 1.54 with sigma of 0.02
 C29-C1GA
 2.8 with sigma of 0.02
 C29-C15 = C17-C15
 1.54 with sigma of 0.02
 O44-C1GA
 1.45 with sigma of 0.02
 C29-C17
 3 with sigma of 0.02
 C1HA-C1
 1.45 with sigma of 0.02
 C6DA-C13 = C6DA-C4FA = C6DA-C246
 1.54 with sigma of 0.02
 C244-C240 = C8BA-C240
 1.45 with sigma of 0.02
3. Restrained planarity
 C231, C249, C1FA, C254, C251, C226
 with sigma of 0.1
 C236, C232, C0FA, C28, C249, C231
 with sigma of 0.1
 C243, C245, C236, C231, C226, C239
 with sigma of 0.1
 C253, C2FA, C7GA, C232, C236, C245
 with sigma of 0.1
4. Rigid body (RIGU) restrains
 C257, C201, C0HA, C34, O30
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C253, C245, C243, C239, C226, C251, C254, C1FA, C249, C231, C236, C232, C0FA,
 C28, C2FA, C7GA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C257, C0HA, C201, C34, O30
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C17, C15, C1GA, O44
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C29, C17, C15, C1GA, O44
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C2HA, C6, C1, C1HA, O113
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
5.a Free rotating group:
 O17(H17J,H17K)
5.b Ternary CH refined with riding coordinates:
 C7CA(H7CA), C96(H96), C123(H123), C168(H168), C191(H191), C193(H193),
 C201(H201), C206(H206), C212(H212), C221(H221), C238(H238), C255(H255),
 C6DA(H6DA), C15(H15O), C1(H1)
5.c Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C80(H80A,H80B), C84(H84A,H84B), C11(H11A,H11B), C40(H40A,
 H40B), C3FA(H3FA,H3FB), C8BA(H8BA,H8BB), C8DA(H8DA,H8DB), C109(H10A,H10B),
 C133(H13M,H13N), C135(H13O,H13P), C155(H15M,H15N), C156(H15P,H15Q), C158(H15R,
 H15S), C164(H16A,H16B), C169(H16C,H16D), C183(H18A,H18B), C186(H18F,H18G),
 C195(H19A,H19B), C204(H20G,H20H), C214(H21O,H21P), C216(H21G,H21H), C233(H23G,
 H23H), C240(H24F,H24G), C244(H24H,H24I), C246(H24D,H24E), C247(H24J,H24K),
 C1GA(H1GA,H1GB), C1HA(H1HA,H1HB)
5.d Aromatic/amide H refined with riding coordinates:
 C23(H23), C26(H26), N28(H28), N32(H32), C33(H33), N37(H37), N42(H42),
 N1AA(H1AA), N49(H49), N52(H52), N56(H56), N58(H58), N59(H59), N65(H65), N9(H9),
  C10(H10), N11(H11), N14(H14), C18(H18), C9EA(H9EA), N3AA(H3AA), N22(H22),
 C25(H25), N0AA(H0AA), C7AA(H7AA), N1BA(H1BA), N45(H45), C4BA(H4BA), C53(H53),
 N55(H55), C56(H56A), C60(H60), C5DA(H5DA), N67(H67), C72(H72), C74(H74),
 N76(H76), C77(H77), N82(H82), C4(H4), C2CA(H2CA), C9(H9A), C12(H12), N13(H13),
 C14(H14A), N15(H15), C16(H16), C22(H22A), C3AA(H3AB), C30(H30), C0BA(H0BA),
 C9GA(H9GA), C35(H35), C37(H37A), C38(H38), C41(H41), C42(H42A), N44(H44),
 C45(H45A), C0DA(H0DA), C2DA(H2DA), C8GA(H8GA), C54(H54), C3DA(H3DA), C62(H62),
 C66(H66), C1CA(H1CA), C5CA(H5CA), C7DA(H7DA), C89(H89), C91(H91), C93(H93),
 C98(H98), C102(H102), C103(H103), C105(H105), C110(H110), C111(H111),
 C120(H120), C121(H121), C125(H125), C126(H126), C128(H128), C130(H130),
 C134(H134), C144(H144), C146(H146), C162(H162), C165(H165), C170(H170),
 C176(H176), C182(H182), C184(H184), C192(H192), C194(H194), C197(H197),
 C203(H203), C208(H208), C215(H215), C222(H222), C234(H234), C239(H239),
 C243(H243), C251(H251), C254(H254), C9FA(H9FA), C0FA(H0FA), C2FA(H2FA),
 C28(H28A), C1FA(H1FA), C7GA(H7GA)
5.e Idealised Me refined as rotating group:
 C6BA(H6BA,H6BB,H6BC), C21(H21A,H21B,H21C), C88(H88A,H88B,H88C), C114(H11C,
 H11D,H11E), C118(H11F,H11G,H11H), C122(H12A,H12B,H12C), C132(H13A,H13B,H13C),
 C136(H13D,H13E,H13F), C139(H13G,H13H,H13I), C151(H15A,H15B,H15C), C152(H15D,
 H15E,H15F), C153(H15G,H15H,H15I), C154(H15J,H15K,H15L), C173(H17A,H17B,H17C),
 C175(H17D,H17E,H17F), C185(H18C,H18D,H18E), C187(H18H,H18I,H18J), C188(H18K,
 H18L,H18M), C198(H19C,H19D,H19E), C202(H20A,H20B,H20C), C209(H20D,H20E,H20F),
 C210(H21D,H21E,H21F), C217(H21I,H21J,H21K), C218(H21L,H21M,H21N), C220(H22B,
 H22C,H22D), C224(H22E,H22F,H22G), C229(H22H,H22I,H22J), C235(H23A,H23B,H23C),
 C237(H23D,H23E,H23F), C241(H24A,H24B,H24C), C252(H25A,H25B,H25C), C257(H25D,
 H25E,H25F), C258(H25G,H25H,H25I), C8FA(H8FA,H8FB,H8FC), C7FA(H7FA,H7FB,H7FC),
 C4FA(H4FA,H4FB,H4FC), C0HA(H0HA,H0HB,H0HC), C2HA(H2HA,H2HB,H2HC), C17(H17G,
 H17H,H17I), C13(H13J,H13K,H13L), C6(H6A,H6B,H6C), C29(H29A,H29B,H29C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              28771
_shelx_hkl_checksum              39511
_shelx_fab_checksum              28169
_olex2_submission_original_sample_id bg-01-207-217
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.235
_oxdiff_exptl_absorpt_empirical_full_min 0.499