Guest recognition enhanced by lateral interactions
Jiao, Tianyu; Cai, Kang; Liu, Zhichang; Wu, Guangcheng; Shen, Libo; Cheng, Chuyang; Feng, Yuanning; Stern, Charlotte L.; Stoddart, J. Fraser; Li, Hao; Chemical Science  (2019) –; doi:10.1039/C9SC00591A

data_1550927
_publ_section_title
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 Guest recognition enhanced by lateral interactions
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00591A
_journal_year                    2019
_chemical_formula_moiety
'6(F6 P), C13 H20 O5, 3(C17 H10 O), H2 O, C78 H60 N12, C2 H3 N'
_chemical_formula_sum            'C144 H115 F36 N13 O9 P6'
_chemical_formula_weight         3041.30
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-01-09 deposited with the CCDC.    2019-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                82.666(2)
_cell_angle_beta                 84.915(2)
_cell_angle_gamma                85.037(2)
_cell_formula_units_Z            2
_cell_length_a                   13.9039(5)
_cell_length_b                   22.9522(9)
_cell_length_c                   23.8176(9)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      50.801
_cell_measurement_theta_min      3.267
_cell_volume                     7487.2(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.01
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            81897
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        46.803
_diffrn_reflns_theta_max         46.803
_diffrn_reflns_theta_min         2.784
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.019
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1298 before and 0.0770 after correction. The Ratio of minimum to maximum transmission is 0.6688. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       prism
_exptl_crystal_F_000             3112
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.162
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.0029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2169
_refine_ls_number_reflns         20061
_refine_ls_number_restraints     2182
_refine_ls_restrained_S_all      1.927
_refine_ls_R_factor_all          0.1841
_refine_ls_R_factor_gt           0.1575
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4366
_refine_ls_wR_factor_ref         0.4621
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13949
_reflns_number_total             20061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00591a2.cif
_cod_data_source_block           wmj18096_0m
_cod_database_code               1550927
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.905
_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 O(H) groups, All O(H,H) groups
2. Restrained distances
 O2-C143
 1.2 with sigma of 0.02
 C143-C142
 1.4 with sigma of 0.02
 O2-C142
 2.4 with sigma of 0.02
 C130-C136
 1.45 with sigma of 0.02
 C111-C110
 1.4 with sigma of 0.02
 O3-C110
 1.2 with sigma of 0.02
 C133-C134 \\sim C131-C130 \\sim C136-C135 \\sim C139-C138 \\sim C127-C132
\\sim C141-C140
 with sigma of 0.01
 F42-F31 \\sim F42-F38 \\sim F42-F36 \\sim F42-F40 \\sim F31-F36 \\sim F31-F35
\\sim F31-F40 \\sim F38-F36
 \\sim F38-F35 \\sim F38-F40 \\sim F36-F35 \\sim F35-F40
 with sigma of 0.02
 P8-F42 \\sim P8-F31 \\sim P8-F38 \\sim P8-F36 \\sim P8-F35 \\sim P8-F40
 with sigma of 0.01
 F41-F32 \\sim F41-F39 \\sim F41-F37 \\sim F41-F33 \\sim F32-F37 \\sim F32-F34
\\sim F32-F33 \\sim F39-F37
 \\sim F39-F34 \\sim F39-F33 \\sim F37-F34 \\sim F34-F33
 with sigma of 0.02
 P9-F41 \\sim P9-F32 \\sim P9-F39 \\sim P9-F37 \\sim P9-F34 \\sim P9-F33
 with sigma of 0.01
 F57-F65 \\sim F57-F55 \\sim F57-F60 \\sim F57-F62 \\sim F66-F65 \\sim F66-F55
\\sim F66-F60 \\sim F66-F62
 \\sim F65-F60 \\sim F65-F62 \\sim F55-F60 \\sim F55-F62
 with sigma of 0.02
 P2-F57 \\sim P2-F66 \\sim P2-F65 \\sim P2-F55 \\sim P2-F60 \\sim P2-F62
 with sigma of 0.01
 F59-F63 \\sim F59-F58 \\sim F59-F64 \\sim F59-F56 \\sim F61-F63 \\sim F61-F58
\\sim F61-F64 \\sim F61-F56
 \\sim F63-F64 \\sim F63-F56 \\sim F58-F64 \\sim F58-F56
 with sigma of 0.02
 P1-F59 \\sim P1-F61 \\sim P1-F63 \\sim P1-F58 \\sim P1-F64 \\sim P1-F56
 with sigma of 0.01
 C122-C121 \\sim C119-C120 \\sim C123-C124 \\sim C118-C117 \\sim C115-C116
\\sim C112-C111 \\sim C113-
 C114 \\sim C126-C125
 with sigma of 0.01
 F20-F19 \\sim F20-F22 \\sim F20-F21 \\sim F19-F29 \\sim F19-F22 \\sim F19-F21
\\sim F29-F22 \\sim F29-F21
 with sigma of 0.02
 F23-F28 \\sim F23-F26 \\sim F23-F25 \\sim F23-F30 \\sim F28-F27 \\sim F28-F26
\\sim F28-F30 \\sim F27-F26
 \\sim F27-F25 \\sim F27-F30 \\sim F26-F25 \\sim F25-F30
 with sigma of 0.02
 F20-F19 \\sim F20-F22 \\sim F20-F24 \\sim F20-F21 \\sim F19-F29 \\sim F19-F22
\\sim F19-F21 \\sim F29-F22
 \\sim F29-F24 \\sim F29-F21 \\sim F22-F24 \\sim F24-F21
 with sigma of 0.02
 P6-F23 \\sim P6-F28 \\sim P6-F27 \\sim P6-F26 \\sim P6-F25 \\sim P6-F30
 with sigma of 0.01
 P7-F20 \\sim P7-F19 \\sim P7-F29 \\sim P7-F22 \\sim P7-F24 \\sim P7-F21
 with sigma of 0.01
 C108-C103 \\sim C108-C107 \\sim C106-C107 \\sim C106-C101 \\sim C101-C102
\\sim C103-C102 \\sim C104-
 C103 \\sim C105-C104 \\sim C105-C95 \\sim C96-C95 \\sim C94-C95 \\sim C94-C93
\\sim C93-C98 \\sim C97-C98
 \\sim C97-C96 \\sim C96-C102 \\sim C97-C99 \\sim C99-C100 \\sim C101-C100
 with sigma of 0.01
3. Rigid bond restraints
 P7, F21, F29, F24, F22, F20, F19, P6, F26, F28, F25, F30, F23, F27
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O2 \\sim C139 \\sim C134 \\sim C127 \\sim C129 \\sim C131 \\sim C143 \\sim C135
\\sim C138 \\sim C137 \\sim C141 \\sim C128 \\sim C130 \\sim C132 \\sim C133
\\sim C142 \\sim C136 \\sim C140: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
P9 \\sim F32 \\sim F39 \\sim F34 \\sim F41 \\sim F37 \\sim F33 \\sim P8 \\sim
F42 \\sim F36 \\sim F35 \\sim F31 \\sim F40 \\sim F38: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
P1 \\sim F61 \\sim F59 \\sim F58 \\sim F56 \\sim F63 \\sim F64 \\sim P2 \\sim
F57 \\sim F66 \\sim F65 \\sim F55 \\sim F60 \\sim F62: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
P7 \\sim F21 \\sim F29 \\sim F24 \\sim F22 \\sim F20 \\sim F19 \\sim P6 \\sim
F26 \\sim F28 \\sim F25 \\sim F30 \\sim F23 \\sim F27: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C99) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 P9, F32, F39, F34, F41, F37, F33, P8, F42, F36, F35, F31, F40, F38
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O2, C139, C134, C127, C129, C131, C143, C135, C138, C137, C141, C128, C130,
 C132, C133, C142, C136, C140
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 P1, F61, F59, F58, F56, F63, F64, P2, F57, F66, F65, F55, F60, F62
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O3, C119, C113, C117, C124, C126, C115, C122, C116, C121, C120, C123, C118,
 C125, C111, C112, C110, C114
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.01
 N13, C145, C144
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 P4, F1, F5, F2, F4, F6, F3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(P8)=Sof(F42)=Sof(F36)=Sof(F35)=Sof(F31)=Sof(F40)=Sof(F38)=1-FVAR(1)
 Sof(P9)=Sof(F32)=Sof(F39)=Sof(F34)=Sof(F41)=Sof(F37)=Sof(F33)=FVAR(1)
 Sof(P6)=Sof(F26)=Sof(F28)=Sof(F25)=Sof(F30)=Sof(F23)=Sof(F27)=1-FVAR(2)
 Sof(P7)=Sof(F21)=Sof(F29)=Sof(F24)=Sof(F22)=Sof(F20)=Sof(F19)=FVAR(2)
 Sof(P2)=Sof(F57)=Sof(F66)=Sof(F65)=Sof(F55)=Sof(F60)=Sof(F62)=1-FVAR(3)
 Sof(P1)=Sof(F61)=Sof(F59)=Sof(F58)=Sof(F56)=Sof(F63)=Sof(F64)=FVAR(3)
 Fixed Sof: H92A(0.5) H92B(0.5) H92C(0.5) H92D(0.5) C91(0.5) H91A(0.5)
 H91B(0.5) P10(0.5) P4(0.5) F52(0.5) F1(0.5) F5(0.5) F2(0.5) F4(0.5) F50(0.5)
 F6(0.5) F47(0.5) F49(0.5) F44(0.5) F45(0.5) F3(0.5) C90(0.5) H90A(0.5)
 H90B(0.5) P11(0.5) F46(0.5) F54(0.5) F51(0.5) F53(0.5) F48(0.5) F43(0.5)
 P5(0.5) F14(0.5) F18(0.5) F16(0.5) F17(0.5) F13(0.5) F15(0.5)
7.a Free rotating group:
 O6(H6A,H6B)
7.b Secondary CH2 refined with riding coordinates:
 C89(H89A,H89B), C87(H87A,H87B), C88(H88A,H88B), C92(H92A,H92B), C92(H92C,
 H92D), C86(H86A,H86B), C84(H84A,H84B), C85(H85A,H85B), C91(H91A,H91B),
 C34(H34A,H34B), C1(H1A,H1B), C41(H41A,H41B), C48(H48A,H48B), C17(H17A,H17B),
 C24(H24A,H24B), C90(H90A,H90B)
7.c Aromatic/amide H refined with riding coordinates:
 C81(H81), C80(H80), C82(H82), C104(H104), C98(H98), C106(H106), C93(H93),
 C100(H100), C99(H99), C107(H107), C105(H105), C109(H109), C94(H94), C113(H113),
  C117(H117), C126(H126), C121(H121), C123(H123), C122(H122), C118(H118),
 C125(H125), C112(H112), C110(H110), C134(H134), C127(H127), C128(H128),
 C132(H132), C143(H143), C138(H138), C137(H137), C133(H133), C140(H140),
 C141(H141), C58(H58), C45(H45), C13(H13), C43(H43), C44(H44), C47(H47),
 C75(H75), C59(H59), C71(H71), C73(H73), C52(H52), C57(H57), C33(H33), C62(H62),
  C30(H30), C12(H12), C78(H78), C56(H56), C31(H31), C19(H19), C6(H6), C49(H49),
 C7(H7), C29(H29), C77(H77), C70(H70), C63(H63), C76(H76), C72(H72), C15(H15),
 C16(H16), C55(H55), C50(H50), C36(H36), C20(H20), C22(H22), C23(H23), C66(H66),
  C68(H68), C38(H38), C67(H67), C37(H37), C65(H65), C60(H60), C4(H4), C53(H53),
 C40(H40), C3(H3)
7.d Fitted hexagon refined as free rotating group:
 C121(C119,C120,C124,C123,C122), C127(C128,C129,C130,C131,C132), C142(C135,
 C136,C139,C140,C141)
7.e Tetrahedral OH refined with riding coordinates:
 O7(H7A)
7.f Idealised Me refined as rotating group:
 C145(H14A,H14B,H14C)
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_shelx_res_checksum              99177
_shelx_fab_checksum              61696
_olex2_submission_special_instructions 'No special instructions were received'