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_7123602
_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         'F6 P, C80 H104 O12, C24 H36 N'
_chemical_formula_sum            'C104 H140 F6 N O12 P'
_chemical_formula_weight         1741.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-04-30
_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                90
_cell_angle_beta                 118.533(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.8683(5)
_cell_length_b                   17.74684(15)
_cell_length_c                   35.1729(5)
_cell_measurement_reflns_used    37526
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      75.9590
_cell_measurement_theta_min      3.4900
_cell_volume                     19121.5(6)
_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_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
  1 omega -114.00  -14.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -57.0000  -90.0000 100

  2 omega  -49.00   33.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   37.0000   60.0000 82

  3 omega  -96.00   -2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  125.0000   60.0000 94

  4 omega  -49.00   30.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   37.0000 -150.0000 79

  5 omega   48.00  116.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 68

  6 omega   38.00  116.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 78

  7 omega   36.00   91.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 55

  8 omega  106.00  178.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -120.0000 72

  9 omega   36.00  159.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000  -90.0000 123

 10 omega   34.00  109.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   90.0000 75

 11 omega   87.00  178.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -60.0000 91

 12 omega   39.00   99.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 60

 13 omega   40.00  125.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -60.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0239245000
_diffrn_orient_matrix_UB_12      0.0762698000
_diffrn_orient_matrix_UB_13      -0.0095693000
_diffrn_orient_matrix_UB_21      0.0279588000
_diffrn_orient_matrix_UB_22      0.0290986000
_diffrn_orient_matrix_UB_23      -0.0200685000
_diffrn_orient_matrix_UB_31      -0.0342792000
_diffrn_orient_matrix_UB_32      -0.0295053000
_diffrn_orient_matrix_UB_33      -0.0446263000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            120249
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         76.893
_diffrn_reflns_theta_min         2.871
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69648
_exptl_absorpt_correction_type   multi-scan
_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)
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    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             7488
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.182
_refine_diff_density_max         2.139
_refine_diff_density_min         -1.842
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2455
_refine_ls_number_reflns         39498
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0948
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1880P)^2^+18.9658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2741
_refine_ls_wR_factor_ref         0.2960
_reflns_Friedel_coverage         0.000
_reflns_number_gt                30863
_reflns_number_total             39498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03341f2.cif
_cod_data_source_block           7_hm4
_cod_original_cell_volume        19121.5(5)
_cod_database_code               7123602
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C80 H100 O20 N2 P1 F6'
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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, All C(H,H,H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(P4) \\sim Ueq, Uanis(P3) \\sim Ueq, Uanis(P2) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(C208) \\sim Ueq, Uanis(C118) \\sim Ueq, Uanis(C122) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
3. Others
 1*[Sof(P2)]+1*[Sof(P3)]+1*[Sof(P4)]=1 with esd of 0.0001
 Sof(H17H)=Sof(H17I)=Sof(H17J)=Sof(C76C)=Sof(H76A)=Sof(H76B)=Sof(C77C)=
 Sof(H77A)=Sof(H77B)=Sof(C75C)=Sof(H75A)=Sof(H75B)=1-FVAR(1)
 Sof(C175)=Sof(H17A)=Sof(H17B)=Sof(H17E)=Sof(H17F)=Sof(H17G)=Sof(C176)=
 Sof(H17K)=Sof(H17L)=Sof(C177)=Sof(H17M)=Sof(H17N)=FVAR(1)
 Sof(H76E)=Sof(H76F)=Sof(H78D)=Sof(H78E)=Sof(H78F)=Sof(O11B)=Sof(C77B)=
 Sof(H77E)=Sof(H77F)=Sof(C75B)=Sof(H75E)=Sof(H75F)=1-FVAR(2)
 Sof(O11)=Sof(H76C)=Sof(H76D)=Sof(C75)=Sof(H75C)=Sof(H75D)=Sof(H78A)=Sof(H78B)=
 Sof(H78C)=Sof(C77)=Sof(H77C)=Sof(H77D)=FVAR(2)
 Sof(C211)=Sof(H21A)=Sof(H21B)=Sof(C210)=Sof(H21C)=Sof(H21D)=Sof(H21E)=
 Sof(C209)=Sof(H20M)=Sof(H20N)=Sof(H20O)=Sof(C216)=Sof(H216)=Sof(C215)=
 Sof(H215)=Sof(C212)=Sof(C214)=Sof(H214)=Sof(C213)=Sof(H213)=1-FVAR(3)
 Sof(C188)=Sof(C186)=Sof(H18O)=Sof(H18P)=Sof(H18Q)=Sof(C185)=Sof(H18R)=
 Sof(H18S)=Sof(H18T)=Sof(C189)=Sof(H189)=Sof(C187)=Sof(H18U)=Sof(H18V)=
 Sof(C190)=Sof(H190)=Sof(C192)=Sof(H192)=Sof(C193)=Sof(H193)=FVAR(3)
 Sof(H20C)=Sof(C218)=Sof(C221)=Sof(C222)=Sof(H22A)=Sof(H22B)=Sof(H22C)=
 Sof(C220)=Sof(H220)=Sof(C219)=Sof(H219)=Sof(C217)=Sof(H217)=Sof(C224)=
 Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C223)=Sof(H22G)=Sof(H22H)=Sof(H22I)=1-FVAR(4)
 Sof(C201)=Sof(H201)=Sof(H200)=Sof(C202)=Sof(C204)=Sof(H204)=Sof(C206)=
 Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C208)=Sof(H20G)=Sof(H20H)=Sof(H20I)=
 Sof(C203)=Sof(H203)=Sof(C205)=Sof(C207)=Sof(H20J)=Sof(H20K)=Sof(H20L)=FVAR(4)
 Fixed Uiso: F7(0.15) F8(0.15) F9(0.15) F10(0.15) F12(0.15) F11(0.15)
4.a Secondary CH2 refined with riding coordinates:
 C144(H14A,H14B), C60(H60A,H60B), C123(H12A,H12B), C163(H16A,H16B), C143(H14C,
 H14D), C124(H12C,H12D), C59(H59A,H59B), C19(H19A,H19B), C80(H80A,H80B),
 C155(H15A,H15B), C183(H18A,H18B), C39(H39A,H39B), C79(H79A,H79B), C12(H12L,
 H12M), C164(H16C,H16D), C94(H94A,H94B), C11(H11L,H11M), C55(H55A,H55B),
 C20(H20A,H20B), C15(H15L,H15M), C40(H40A,H40B), C17(H17O,H17P), C16(H16L,H16M),
  C184(H18C,H18D), C83(H83A,H83B), C71(H71A,H71B), C175(H17A,H17B), C157(H15C,
 H15D), C13(H13L,H13M), C159(H15E,H15F), C139(H13A,H13B), C56(H56A,H56B),
 C76(H76C,H76D), C76(H76E,H76F), C135(H13C,H13D), C198(H19C,H19D), C35(H35A,
 H35B), C72(H72A,H72B), C156(H15J,H15K), C57(H57A,H57B), C75(H75C,H75D),
 C32(H32A,H32B), C140(H14E,H14F), C119(H11A,H11B), C73(H73A,H73B), C31(H31A,
 H31B), C115(H11C,H11D), C141(H14G,H14H), C51(H51A,H51B), C37(H37A,H37B),
 C36(H36A,H36B), C136(H13E,H13F), C160(H16H,H16I), C161(H16J,H16K), C179(H17C,
 H17D), C33(H33A,H33B), C180(H18E,H18F), C181(H18G,H18H), C116(H11E,H11F),
 C77(H77C,H77D), C137(H13G,H13H), C120(H12E,H12F), C117(H11G,H11H), C187(H18U,
 H18V), C176(H17K,H17L), C52(H52A,H52B), C121(H12G,H12H), C177(H17M,H17N),
 C53(H53A,H53B), C211(H21A,H21B), C76C(H76A,H76B), C77C(H77A,H77B), C75C(H75A,
 H75B), C77B(H77E,H77F), C75B(H75E,H75F)
4.b Me refined with riding coordinates:
 C78(H78A,H78B,H78C), C78(H78D,H78E,H78F), C178(H17E,H17F,H17G), C178(H17H,
 H17I,H17J)
4.c Aromatic/amide H refined with riding coordinates:
 C131(H131), C7(H7), C168(H168), C50(H50), C111(H111), C10(H10), C169(H169),
 C154(H154), C151(H151), C67(H67), C24(H24), C47(H47), C132(H132), C9(H9),
 C114(H114), C112(H112), C96(H96), C27(H27), C171(H171), C153(H153), C48(H48),
 C28(H28), C8(H8), C25(H25), C113(H113), C100(H100), C64(H64), C172(H172),
 C68(H68), C128(H128), C152(H152), C97(H97), C65(H65), C99(H99), C86(H86),
 C49(H49), C88(H88), C85(H85), C129(H129), C201(H201), C89(H89), C200(H200),
 C200(H20C), C204(H204), C203(H203), C189(H189), C190(H190), C192(H192),
 C193(H193), C216(H216), C215(H215), C214(H214), C213(H213), C220(H220),
 C219(H219), C217(H217)
4.d Idealised Me refined as rotating group:
 C82(H82A,H82B,H82C), C81(H81A,H81B,H81C), C104(H10A,H10B,H10C), C91(H91A,H91B,
 H91C), C158(H15G,H15H,H15I), C74(H74A,H74B,H74C), C14(H14L,H14M,H14N),
 C162(H16E,H16F,H16G), C18(H18L,H18M,H18N), C93(H93A,H93B,H93C), C58(H58A,H58B,
 H58C), C34(H34A,H34B,H34C), C92(H92A,H92B,H92C), C102(H10D,H10E,H10F),
 C206(H20D,H20E,H20F), C142(H14I,H14J,H14K), C103(H10G,H10H,H10I), C196(H19E,
 H19F,H19G), C197(H19H,H19I,H19J), C208(H20G,H20H,H20I), C186(H18O,H18P,H18Q),
 C195(H19K,H19L,H19M), C138(H13I,H13J,H13K), C185(H18R,H18S,H18T), C207(H20J,
 H20K,H20L), C38(H38A,H38B,H38C), C118(H11I,H11J,H11K), C182(H18I,H18J,H18K),
 C122(H12I,H12J,H12K), C210(H21C,H21D,H21E), C209(H20M,H20N,H20O), C54(H54A,
 H54B,H54C), C222(H22A,H22B,H22C), C224(H22D,H22E,H22F), C223(H22G,H22H,H22I)
;
_shelx_res_checksum              95210
_olex2_submission_special_instructions 'No special instructions were received'