Probing the Guest-Binding Preference of Three Structurally Similar and Conformationally Adaptive Macrocycles
Chai, Hongxin; Pan, Zhi-Sheng; Yang, Liu-Pan; He, Shan; Pan, Fangfang; Rissanen, Kari; Jiang, Wei; Chemical Communications  (2019) –; doi:10.1039/C9CC03341F

data_7123603
_publ_section_title
;
 Probing the Guest-Binding Preference of Three Structurally Similar and
 Conformationally Adaptive Macrocycles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03341F
_journal_year                    2019
_chemical_formula_moiety
'2(C80 H104 O12), 2(C28 H42 N2), 4(F6 P), 9(C2 H3 N)'
_chemical_formula_sum            'C234 H319 F24 N13 O24 P4'
_chemical_formula_weight         4277.88
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-05-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-05-31 deposited with the CCDC.    2019-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                76.681(3)
_cell_angle_beta                 82.212(3)
_cell_angle_gamma                86.269(3)
_cell_formula_units_Z            2
_cell_length_a                   17.6647(7)
_cell_length_b                   24.7902(10)
_cell_length_c                   26.8978(11)
_cell_measurement_reflns_used    6842
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      25.0450
_cell_measurement_theta_min      3.3770
_cell_volume                     11349.3(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega  -47.00   43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.7586   77.0000 -120.0000 90

  2 omega  -55.00   42.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9305  -37.0000  -30.0000 97

  3 omega  -19.00   25.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.7586  -99.0000  120.0000 44

  4 omega   -7.00   84.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9305   37.0000  150.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0387352000
_diffrn_orient_matrix_UB_12      -0.0070299000
_diffrn_orient_matrix_UB_13      0.0019022000
_diffrn_orient_matrix_UB_21      0.0032002000
_diffrn_orient_matrix_UB_22      -0.0180082000
_diffrn_orient_matrix_UB_23      0.0243369000
_diffrn_orient_matrix_UB_31      -0.0115684000
_diffrn_orient_matrix_UB_32      0.0221785000
_diffrn_orient_matrix_UB_33      0.0122453000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.1679
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            65707
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         3.008
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             4564
_exptl_crystal_size_max          0.584
_exptl_crystal_size_mid          0.5085
_exptl_crystal_size_min          0.2199
_refine_diff_density_max         1.247
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2976
_refine_ls_number_reflns         40660
_refine_ls_number_restraints     516
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.2346
_refine_ls_R_factor_gt           0.1109
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1549P)^2^+16.2629P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2690
_refine_ls_wR_factor_ref         0.3682
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16969
_reflns_number_total             40660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03341f2.cif
_cod_data_source_block           8_hm4
_cod_database_code               7123603
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C50 H50 O6 N4 P2 F12'
_reflns_odcompleteness_completeness 96.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H13F,H13G,H13H,H13I,H13D,H13E} of C130, All C(H,H) groups,
   All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, {H13O,H13P,H13Q,H13L,H13M,H13N} of C132, {H60A,H60B,
  H60C,H60D,H60E,H60F} of C60, {H23C,H23D,H23E,H23F,H23G,H23H} of C232
2. Restrained distances
 C219-C220
 1.4 with sigma of 0.02
 C21C-C22C = C159-C160
 1.54 with sigma of 0.02
 C153-C154 = C154-C155 = C155-C156 = C131-C130 = C158-C159 = C21C-C158
 1.54 with sigma of 0.02
 C63B-C62 = C66-C67 = C67-C68 = C75B-C74 = C219-C220 = C150-C1K = C1J-C1K
 1.54 with sigma of 0.02
 C1K-C149
 2.54 with sigma of 0.01
 C157-C21C = C158-C160 = O22-C158
 2.52 with sigma of 0.04
 H15L-H1JB = H15L-H1JC
 2.2 with sigma of 0.04
 H17G-H68D
 2.2 with sigma of 0.04
 C67-C66 \\sim C66-C67B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F4) \\sim Ueq, Uanis(N6) \\sim Ueq, Uanis(N11) \\sim Ueq: with sigma of
0.003 and sigma for terminal atoms of 0.006
Uanis(F6) \\sim Ueq, Uanis(F13) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(C52) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C148) \\sim Ueq, Uanis(C175)
\\sim Ueq, Uanis(C218) \\sim Ueq, Uanis(C220) \\sim Ueq, Uanis(C230) \\sim Ueq,
Uanis(F3) \\sim Ueq, Uanis(F21) \\sim Ueq, Uanis(F23) \\sim Ueq, Uanis(N5)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C57) \\sim Ueq, Uanis(C58) \\sim Ueq, Uanis(C59B) \\sim Ueq, Uanis(C62)
\\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C63B) \\sim Ueq,
Uanis(C64B) \\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(C67B) \\sim Ueq, Uanis(C68B)
\\sim Ueq, Uanis(C70) \\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C72) \\sim Ueq,
Uanis(C72B) \\sim Ueq, Uanis(C75B) \\sim Ueq, Uanis(C76B) \\sim Ueq, Uanis(C79)
\\sim Ueq, Uanis(C80) \\sim Ueq, Uanis(C130) \\sim Ueq, Uanis(C131) \\sim Ueq,
Uanis(C138) \\sim Ueq, Uanis(C135) \\sim Ueq, Uanis(C136) \\sim Ueq,
Uanis(C140) \\sim Ueq, Uanis(C143) \\sim Ueq, Uanis(C144) \\sim Ueq,
Uanis(C145) \\sim Ueq, Uanis(C146) \\sim Ueq, Uanis(C147) \\sim Ueq,
Uanis(C149) \\sim Ueq, Uanis(C152) \\sim Ueq, Uanis(C153) \\sim Ueq,
Uanis(C157) \\sim Ueq, Uanis(C158) \\sim Ueq, Uanis(C159) \\sim Ueq,
Uanis(C160) \\sim Ueq, Uanis(C219) \\sim Ueq, Uanis(C223) \\sim Ueq,
Uanis(C227) \\sim Ueq, Uanis(C229) \\sim Ueq, Uanis(C231) \\sim Ueq, Uanis(C1J)
\\sim Ueq, Uanis(C1K) \\sim Ueq, Uanis(C5C) \\sim Ueq, Uanis(C6C) \\sim Ueq,
Uanis(C11C) \\sim Ueq, Uanis(C12C) \\sim Ueq, Uanis(C13C) \\sim Ueq,
Uanis(C14C) \\sim Ueq, Uanis(C15C) \\sim Ueq, Uanis(C17C) \\sim Ueq,
Uanis(C18C) \\sim Ueq, Uanis(C19C) \\sim Ueq, Uanis(C21C) \\sim Ueq,
Uanis(C22C) \\sim Ueq, Uanis(F19) \\sim Ueq, Uanis(F20) \\sim Ueq, Uanis(F22)
\\sim Ueq, Uanis(F24) \\sim Ueq, Uanis(N8) \\sim Ueq, Uanis(N14) \\sim Ueq,
Uanis(C221) \\sim Ueq, Uanis(C232) \\sim Ueq, Uanis(O22) \\sim Ueq, Uanis(N15)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C159) = Uanis(C160)
Uanis(C22C) = Uanis(C21C)
Uanis(C158) = Uanis(C157)
Uanis(C151) = Uanis(C1K)
4. Others
 Fixed Sof: H57A(0.55) H57B(0.55) H57C(0.45) H57D(0.45) C58(0.55) H58A(0.55)
 H58B(0.55) C58B(0.45) H58C(0.45) H58D(0.45) C59(0.55) H59A(0.55) H59B(0.55)
 C59B(0.45) H59C(0.45) H59D(0.45) H60A(0.55) H60B(0.55) H60C(0.55) H60D(0.45)
 H60E(0.45) H60F(0.45) H62A(0.65) H62B(0.65) H62C(0.35) H62D(0.35) C63(0.65)
 H63A(0.65) H63B(0.65) C63B(0.35) H63C(0.35) H63D(0.35) C64(0.65) H64A(0.65)
 H64B(0.65) H64C(0.65) C64B(0.35) H64D(0.35) H64E(0.35) H64F(0.35) H66A(0.65)
 H66B(0.65) H66C(0.35) H66D(0.35) C67(0.65) H67A(0.65) H67B(0.65) C67B(0.35)
 H67C(0.35) H67D(0.35) C68(0.65) H68A(0.65) H68B(0.65) H68C(0.65) C68B(0.35)
 H68D(0.35) H68E(0.35) H68F(0.35) H71A(0.6) H71B(0.6) H71C(0.4) H71D(0.4)
 C72(0.6) H72A(0.6) H72B(0.6) H72C(0.6) C72B(0.4) H72D(0.4) H72E(0.4) H72F(0.4)
 H74A(0.7) H74B(0.7) H74C(0.3) H74D(0.3) C75(0.7) H75A(0.7) H75B(0.7) C75B(0.3)
 H75C(0.3) H75D(0.3) C76(0.7) H76A(0.7) H76B(0.7) H76C(0.7) C76B(0.3) H76D(0.3)
 H76E(0.3) H76F(0.3) C1C(0.6) H1CA(0.6) H1CB(0.6) C1J(0.35) H1JA(0.35)
 H1JB(0.35) H1JC(0.35) C1K(0.35) H1KA(0.35) H1KB(0.35) C2C(0.6) H2CA(0.6)
 H2CB(0.6) C3C(0.6) H3CA(0.6) H3CB(0.6) H3CC(0.6) C4C(0.33333) H4CA(0.33333)
 H4CB(0.33333) C5C(0.33333) H5CA(0.33333) H5CB(0.33333) C6C(0.33333)
 H6CA(0.33333) H6CB(0.33333) H6CC(0.33333) C11C(0.5) H11A(0.5) H11B(0.5)
 C12C(0.5) H12A(0.5) H12B(0.5) C13C(0.5) H13A(0.5) H13B(0.5) H13C(0.5)
 C21C(0.5) H21A(0.5) H21B(0.5) C22C(0.5) H22A(0.5) H22B(0.5) H22C(0.5)
 H13F(0.33333) H13G(0.33333) H13H(0.33333) H13I(0.33333) H13D(0.33333)
 H13E(0.33333) C131(0.33333) H13J(0.33333) H13K(0.33333) C132(0.66667)
 H13O(0.33333) H13P(0.33333) H13Q(0.33333) H13L(0.33333) H13M(0.33333)
 H13N(0.33333) H13Z(0.7) HA(0.7) HB(0.3) HC(0.3) C138(0.4) H13(0.4) HD(0.4)
 C139(0.4) H0AA(0.4) HE(0.4) C140(0.4) H14A(0.4) H14B(0.4) H14C(0.4) H14D(0.5)
 H14E(0.5) H14F(0.5) H14G(0.5) C142(0.5) H14H(0.5) H14I(0.5) C143(0.5)
 H14J(0.5) H14K(0.5) C144(0.5) H14L(0.5) H14M(0.5) H14N(0.5) H15A(0.35)
 H15B(0.35) H15C(0.65) H15D(0.65) C151(0.65) H15E(0.65) H15F(0.65) C152(0.65)
 H15G(0.65) H15H(0.65) H15I(0.65) H15U(0.5) H15V(0.5) H15W(0.5) H15X(0.5)
 C159(0.5) H15Y(0.5) HF(0.5) C160(0.5) H16A(0.5) H16B(0.5) H16C(0.5) C14C(0.5)
 H14Z(0.5) HG(0.5) HH(0.5) C15C(0.5) H15Z(0.5) HI(0.5) HJ(0.5) C16C(0.5)
 H16D(0.5) H16E(0.5) H16F(0.5) C17C(0.5) H17A(0.5) H17B(0.5) H17C(0.5)
 C18C(0.5) H18A(0.5) H18B(0.5) H18C(0.5) C19C(0.5) H19A(0.5) H19B(0.5)
 H19C(0.5) P4(0.5) P4B(0.5) C233(0.25) C234(0.25) H23L(0.25) H23M(0.25)
 H23N(0.25) N13(0.25) C225(0.75) C226(0.75) H22P(0.75) H22Q(0.75) H22R(0.75)
 N12(0.75) C231(0.4) H23C(0.4) H23D(0.4) H23E(0.4) H23F(0.6) H23G(0.6)
 H23H(0.6) C237(0.6) N14(0.6) N15(0.4)
 Fixed Uiso: C154(0.14) C155(0.16) C156(0.18)
5.a Riding coordinates:
 C22C(H22A,H22B,H22C), C232(H23C,H23D,H23E), C232(H23F,H23G,H23H)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11G,H11H), C12(H12I,H12J), C23(H23A,H23B), C24(H24A,H24B), C35(H35A,
 H35B), C36(H36A,H36B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B),
 C50(H50A,H50B), C51(H51A,H51B), C53(H53A,H53B), C54(H54A,H54B), C55(H55A,H55B),
  C57(H57A,H57B), C57(H57C,H57D), C58(H58A,H58B), C58B(H58C,H58D), C59(H59A,
 H59B), C59B(H59C,H59D), C61(H61A,H61B), C62(H62A,H62B), C62(H62C,H62D),
 C63(H63A,H63B), C63B(H63C,H63D), C65(H65A,H65B), C66(H66A,H66B), C66(H66C,
 H66D), C67(H67A,H67B), C67B(H67C,H67D), C69(H69A,H69B), C70(H70A,H70B),
 C71(H71A,H71B), C71(H71C,H71D), C73(H73A,H73B), C74(H74A,H74B), C74(H74C,H74D),
  C75(H75A,H75B), C75B(H75C,H75D), C77(H77A,H77B), C78(H78A,H78B), C79(H79A,
 H79B), C1C(H1CA,H1CB), C1K(H1KA,H1KB), C2C(H2CA,H2CB), C4C(H4CA,H4CB),
 C5C(H5CA,H5CB), C11C(H11A,H11B), C12C(H12A,H12B), C21C(H21A,H21B), C91(H91A,
 H91B), C92(H92A,H92B), C103(H10A,H10B), C104(H10C,H10D), C115(H11C,H11D),
 C116(H11E,H11F), C127(H12C,H12D), C128(H12E,H12F), C129(H12G,H12H), C130(H13F,
 H13G), C130(H13H,H13I), C130(H13D,H13E), C131(H13J,H13K), C133(H13R,H13S),
 C134(H13T,H13U), C135(H13V,H13W), C137(H13Z,HA), C137(HB,HC), C138(H13,HD),
 C139(H0AA,HE), C141(H14D,H14E), C141(H14F,H14G), C142(H14H,H14I), C143(H14J,
 H14K), C145(H14O,H14P), C146(H14Q,H14R), C147(H14S,H14T), C149(H14X,H14Y),
 C150(H15A,H15B), C150(H15C,H15D), C151(H15E,H15F), C153(H15J,H15K), C154(H15L,
 H15M), C155(H15N,H15O), C157(H15S,H15T), C158(H15U,H15V), C158(H15W,H15X),
 C159(H15Y,HF), C189(H18D,H18E), C190(H19D,H19E), C191(H19F,H19G), C192(H19H,
 H19I), C193(H19J,H19K), C194(H19L,H19M), C195(H19N,H19O), C206(H20J,H20K),
 C161(H16G,H16H), C162(H16I,H16J), C163(H16K,H16L), C164(H16M,H16N), C165(H16O,
 H16P), C166(H16Q,H16R), C167(H16S,H16T), C178(H17M,H17N)
5.c Me refined with riding coordinates:
 C60(H60A,H60B,H60C), C60(H60D,H60E,H60F)
5.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C19(H19), C20(H20),
 C31(H31), C32(H32), C33(H33), C34(H34), C39(H39), C40(H40), C43(H43), C44(H44),
  C87(H87), C88(H88), C89(H89), C90(H90), C95(H95), C96(H96), C99(H99),
 C100(H100), C111(H111), C112(H112), C113(H113), C114(H114), C119(H119),
 C120(H120), C123(H123), C124(H124), C197(H197), C198(H198), C200(H200),
 C201(H201), C208(H208), C209(H209), C211(H211), C212(H212), C169(H169),
 C170(H170), C172(H172), C173(H173), C180(H180), C181(H181), C183(H183),
 C184(H184)
5.e Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C56(H56A,H56B,H56C), C64(H64A,H64B,H64C), C64B(H64D,H64E,
 H64F), C68(H68A,H68B,H68C), C68B(H68D,H68E,H68F), C72(H72A,H72B,H72C),
 C72B(H72D,H72E,H72F), C76(H76A,H76B,H76C), C76B(H76D,H76E,H76F), C80(H80A,H80B,
 H80C), C1J(H1JA,H1JB,H1JC), C3C(H3CA,H3CB,H3CC), C6C(H6CA,H6CB,H6CC),
 C13C(H13A,H13B,H13C), C132(H13O,H13P,H13Q), C132(H13L,H13M,H13N), C136(H13X,
 H13Y,H), C140(H14A,H14B,H14C), C144(H14L,H14M,H14N), C148(H14U,H14V,H14W),
 C152(H15G,H15H,H15I), C156(H15P,H15Q,H15R), C160(H16A,H16B,H16C), C14C(H14Z,HG,
 HH), C15C(H15Z,HI,HJ), C16C(H16D,H16E,H16F), C17C(H17A,H17B,H17C), C18C(H18A,
 H18B,H18C), C19C(H19A,H19B,H19C), C203(H20A,H20B,H20C), C204(H20D,H20E,H20F),
 C205(H20G,H20H,H20I), C175(H17D,H17E,H17F), C176(H17G,H17H,H17I), C177(H17J,
 H17K,H17L), C186(H18F,H18G,H18H), C187(H18I,H18J,H18K), C188(H18L,H18M,H18N),
 C236(H23I,H23J,H23K), C220(H22D,H22E,H22F), C234(H23L,H23M,H23N), C228(H22G,
 H22H,H22I), C230(H23O,H23P,H23Q), C222(H22J,H22K,H22L), C218(H21C,H21D,H21E),
 C224(H22M,H22N,H22O), C226(H22P,H22Q,H22R)
;
_shelx_res_checksum              53879
_olex2_submission_special_instructions 'No special instructions were received'