Stereoselective synthesis of a composite knot with nine crossings
Liang Zhang; Alexander J. Stephens; Alina L. Nussbaumer; Jean-Francois Lemonnier; Pia Jurcek; Inigo J. Vitorica-Yrezabal; David A. Leigh; Nature Chemistry 10 (2018) 1083–1088; doi:10.1038/s41557-018-0124-6

data_1551500
_publ_section_title
;
 Stereoselective synthesis of a composite knot with nine crossings
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              1083
_journal_page_last               1088
_journal_paper_doi               10.1038/s41557-018-0124-6
_journal_volume                  10
_journal_year                    2018
_chemical_formula_moiety         '1(C384 Fe6 N36 O24), 5(F6 P1)'
_chemical_formula_sum            'C384 H306 F30 Fe6 N36 O24 P5'
_chemical_formula_weight         6868.65
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   .
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   47.726(5)
_cell_length_b                   47.726(5)
_cell_length_c                   39.415(8)
_cell_measurement_reflns_used    1847
_cell_measurement_temperature    100
_cell_measurement_theta_max      10.9860
_cell_measurement_theta_min      1.6470
_cell_volume                     77750(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector
;
Photon counting pixel array data_PILATUS_2M_S_N_24_0107_Diamond
;
_diffrn_measured_fraction_theta_full 0.094
_diffrn_measured_fraction_theta_max 0.953
_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   -145.00  24.00   1.00    0.20    --   30.00   0.00   0.00  169
;
_diffrn_measurement_device       'Fixed \c 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0005031000
_diffrn_orient_matrix_UB_12      0.0005083000
_diffrn_orient_matrix_UB_13      -0.0174807000
_diffrn_orient_matrix_UB_21      -0.0112183000
_diffrn_orient_matrix_UB_22      0.0050868000
_diffrn_orient_matrix_UB_23      -0.0001057000
_diffrn_orient_matrix_UB_31      0.0123323000
_diffrn_orient_matrix_UB_32      0.0158250000
_diffrn_orient_matrix_UB_33      0.0006028000
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.094
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6655
_diffrn_reflns_point_group_measured_fraction_full 0.094
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         11.024
_diffrn_reflns_theta_min         1.612
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.880
_exptl_crystal_description       plate
_exptl_crystal_F_000             21330
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.122
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.608
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     389
_refine_ls_restrained_S_all      3.180
_refine_ls_R_factor_all          0.3430
_refine_ls_R_factor_gt           0.2678
_refine_ls_shift/su_max          0.069
_refine_ls_shift/su_mean         0.001
_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          0.5742
_refine_ls_wR_factor_ref         0.6393
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1440
_reflns_number_total             2948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            41557_2018_124_MOESM30_ESM.cif
_cod_data_source_block           m_973_ck_collection_
_cod_original_cell_volume        77749(23)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               1551500
_reflns_odcompleteness_completeness 95.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     11.02
_olex2_refinement_description
;
1. Restrained distances
 C133-C135
 2.4 with sigma of 0.02
 C131-C135
 2.4 with sigma of 0.02
 C140-C132
 2.4 with sigma of 0.02
 C132-C136
 2.4 with sigma of 0.02
 C137-C141
 2.4 with sigma of 0.02
 C58-C61
 1.45 with sigma of 0.02
 C57-C61
 2.4 with sigma of 0.02
 C59-C61
 2.4 with sigma of 0.02
 O54-C55
 1.45 with sigma of 0.02
 C56-O54
 2.4 with sigma of 0.02
 C60-O54
 2.4 with sigma of 0.02
 C51-O54
 1.45 with sigma of 0.02
 C52-O54
 2.4 with sigma of 0.02
 C50-O54
 2.4 with sigma of 0.02
 C51-C55
 2.4 with sigma of 0.02
 C129-O128
 1.45 with sigma of 0.02
 O128-C130
 2.4 with sigma of 0.02
 C134-O128
 2.4 with sigma of 0.02
 C48-O47
 1.45 with sigma of 0.02
 O47-C53
 2.4 with sigma of 0.02
 C49-O47
 2.4 with sigma of 0.02
 O47-C46
 1.45 with sigma of 0.02
 C46-C48
 2.4 with sigma of 0.02
 C41-C42
 1.54 with sigma of 0.02
 N22-C18
 2.4 with sigma of 0.02
 C46-C42
 4 with sigma of 0.02
 C64-N72
 2.4 with sigma of 0.02
 C68-C64
 2.4 with sigma of 0.02
 C88-C87
 1.54 with sigma of 0.02
 C138-C141
 1.4 with sigma of 0.02
 C142-C138
 2.4 with sigma of 0.02
 N0AA-C138
 2.4 with sigma of 0.02
 C74-C80
 2.4 with sigma of 0.02
 N1-C8
 2.4 with sigma of 0.02
 C8-C5
 2.4 with sigma of 0.02
 C8-C6
 1.4 with sigma of 0.02
 C6-C9
 2.4 with sigma of 0.02
 C6-N7
 2.4 with sigma of 0.02
 C18-C21
 1.4 with sigma of 0.02
 C14-C20
 2.4 with sigma of 0.02
 C16-C14
 2.4 with sigma of 0.02
 C64-Fe2
 2.8 with sigma of 0.02
 C66-Fe2
 2.8 with sigma of 0.02
 C146_$2-C147_$1
 1.54 with sigma of 0.02
 C73-C74
 1.54 with sigma of 0.02
 C70-C73
 1.45 with sigma of 0.02
 C75-C74
 1.45 with sigma of 0.02
 C120-O121
 1.45 with sigma of 0.02
 C115-C116
 1.54 with sigma of 0.02
 C118-C120
 2.4 with sigma of 0.02
 C117-C118
 1.54 with sigma of 0.02
 C116-C118
 2.4 with sigma of 0.02
 C116-C117
 1.54 with sigma of 0.02
 C118-C116
 2.4 with sigma of 0.02
 C115-C117
 2.4 with sigma of 0.02
 C13-C14
 1.54 with sigma of 0.02
 C145-C146
 2.4 with sigma of 0.003
 C146-C143
 2.4 with sigma of 0.003
 O128-C125
 1.45 with sigma of 0.02
 O128-C126
 2.4 with sigma of 0.02
 O128-C124
 2.4 with sigma of 0.02
 O121-C122
 1.45 with sigma of 0.02
 C120-C122
 2.4 with sigma of 0.02
 C42-C37
 3 with sigma of 0.02
 C41-C37
 2.4 with sigma of 0.02
 C42_$1-C43_$1
 1.54 with sigma of 0.02
 C43-C41
 2.4 with sigma of 0.02
 C87-C85 = C88-C89
 1.54 with sigma of 0.02
 C24-C27
 1.45 with sigma of 0.02
 O33-C30
 1.45 with sigma of 0.02
 O33-C29
 2.4 with sigma of 0.02
 O33-C31
 2.4 with sigma of 0.02
 C27-C23
 2.4 with sigma of 0.02
 C25-C32
 2.4 with sigma of 0.02
 C32-C24
 2.4 with sigma of 0.02
 C28-C24
 2.4 with sigma of 0.02
 C44-C46
 2.4 with sigma of 0.02
 C43-C44
 1.35 with sigma of 0.02
 C42_$1-C44_$1
 2.4 with sigma of 0.02
 C119-C120
 1.54 with sigma of 0.02
 C119-O121
 2.4 with sigma of 0.02
 C118-C119
 1.54 with sigma of 0.02
 C117-C119
 2.4 with sigma of 0.02
 C116-C119
 3.2 with sigma of 0.02
 C119-C127
 3 with sigma of 0.02
 C13-C11 = C15-C14
 1.54 with sigma of 0.02
 F104-P0A = F109-P0A
 1.4 with sigma of 0.02
 P0A-F104_$2 = P0A-F109 = P0A-F109_$1 = P0A-F109_$2 = P0A-F104_$1 = P0A-F104
 1.6 with sigma of 0.02
 F109-F109_$2
 2.26 with sigma of 0.002
 F109_$2-F104_$1 = F109_$1-F104 = F109-F104_$2
 2.26 with sigma of 0.002
 F104_$1-F104_$2
 2.26 with sigma of 0.002
 F104-F104_$1
 2.26 with sigma of 0.002
 F109_$2-F109_$1
 2.26 with sigma of 0.002
 F109-F109_$1
 2.26 with sigma of 0.002
 F109-F104
 2.26 with sigma of 0.002
 C45-C46
 1.54 with sigma of 0.02
 O47-C45
 2.4 with sigma of 0.02
 C45-C43
 2.4 with sigma of 0.02
 C45-C44
 1.54 with sigma of 0.02
 C41-O40
 1.45 with sigma of 0.02
 C42-O40
 2.4 with sigma of 0.02
 O40-C37
 1.45 with sigma of 0.02
 P1-F4AA = P1-F4 = P1-F5 = P1-F3 = P1-F2 = P1-F26
 1.6 with sigma of 0.02
 F4AA-F4 = F4AA-F26
 2.2 with sigma of 0.02
 F4-F5
 2.2 with sigma of 0.02
 F5-F2
 2.2 with sigma of 0.02
 F2-F4AA
 2.2 with sigma of 0.02
 F26-F2
 2.2 with sigma of 0.02
 F26-F5
 2.2 with sigma of 0.02
 F26-F4
 2.2 with sigma of 0.02
 F3-F4
 2.2 with sigma of 0.02
 F3-F5
 2.2 with sigma of 0.02
 F3-F2
 2.2 with sigma of 0.02
 F3-F4AA
 2.2 with sigma of 0.02
 P2-F0AA = P2-F23 = P2-F18 = P2-F14 = P2-F17 = P2-F1
 1.6 with sigma of 0.02
 F18-F0AA = F23-F0AA = F14-F0AA = F18-F17 = F17-F1
 2.2 with sigma of 0.02
 F17-F14 = F23-F1
 2.2 with sigma of 0.02
 F14-F18
 2.2 with sigma of 0.02
 F14-F1
 2.2 with sigma of 0.02
 F14-F23
 2.2 with sigma of 0.02
 F18-F17
 2.2 with sigma of 0.02
 F18-F1
 2.2 with sigma of 0.02
 F17-F1
 2.2 with sigma of 0.02
 F17-F23
 2.2 with sigma of 0.02
 F17-F0AA
 2.2 with sigma of 0.02
 F17-F18
 2.2 with sigma of 0.02
 O107-C104
 1.45 with sigma of 0.02
 C105-O107
 2.4 with sigma of 0.02
 C103-O107
 2.4 with sigma of 0.02
 C116-O114_$2
 2.4 with sigma of 0.02
 C115-O114_$2
 1.45 with sigma of 0.02
 C111-O114
 1.45 with sigma of 0.02
 C104-C108
 2.4 with sigma of 0.02
 C115-C111_$2
 2.4 with sigma of 0.02
 C3-C147
 1.45 with sigma of 0.02
 C127-O121 \\sim O121-C123
 with sigma of 0.002
 C39-O33 \\sim O33-C35
 with sigma of 0.02
 O33-C30 \\sim O33-C34
 with sigma of 0.02
 O33-C35 \\sim C34-C30
 with sigma of 0.002
 N0AA-C138 \\sim C138-C142
 with sigma of 0.02
 C137-C141 \\sim C141-N139
 with sigma of 0.02
 C106-C98 \\sim C98-C102
 with sigma of 0.02
 C102-C98 \\sim C98-C106
 with sigma of 0.02
 C98-C101 \\sim C92-C95
 with sigma of 0.02
 N96-C92 \\sim C92-C100
 with sigma of 0.02
 C91-C95 \\sim C95-N93
 with sigma of 0.02
 C86-Fe1 \\sim Fe1-C82
 with sigma of 0.0002
 C14-C11 \\sim C13-C15
 with sigma of 0.002
 C12-C13 \\sim C13-C10
 with sigma of 0.002
 C38-O40 \\sim O40-C36
 with sigma of 0.002
 O47-C44 \\sim C43-O40
 with sigma of 0.02
 O40-C42 \\sim C45-O47
 with sigma of 0.002
 O40-C44 \\sim O47-C43
 with sigma of 0.02
 C109-O107 \\sim O107-C113
 with sigma of 0.002
 C112-O114 \\sim O114-C110
 with sigma of 0.002
2. Restrained planarity
 C145, C144, C143, C146
 with sigma of 0.1
 C135, C131, C132, C133
 with sigma of 0.1
 C136, C135, C140, C132
 with sigma of 0.1
 C61, C57, C58, C59
 with sigma of 0.1
 C66, C62, C61, C58
 with sigma of 0.1
 O54, C60, C55, C56
 with sigma of 0.1
 O54, C50, C51, C52
 with sigma of 0.1
 C129, C130, C134, O128
 with sigma of 0.1
 C48, C49, C53, O47
 with sigma of 0.1
 O128, C125, C124, C126
 with sigma of 0.1
 C123, C122, C127, O121
 with sigma of 0.1
 O33, C34, C39, C35
 with sigma of 0.1
 C29, C30, C31, O33
 with sigma of 0.1
 C24, C27, C28, C32
 with sigma of 0.1
 C21, C26, C25, C24, C23, N22, C27
 with sigma of 0.002
 N0AA, C145, C144, C143, C142, C141, C138, C137, C136, C135, C140, N139
 with sigma of 0.1
 C118, C117, C119, C116
 with sigma of 0.1
 C98, C105, C104, C103, C102, C101, C106
 with sigma of 0.1
 N96, C95, C100, C99, C98, C97, C101
 with sigma of 0.1
 N96, C95, C100, C99, C98, C97, C92
 with sigma of 0.1
 C21, C15, C16, N17, C18, C19, C20
 with sigma of 0.1
 C21, C26, C25, C24, C23, N22, C18
 with sigma of 0.1
 C45, C44, C43, C42
 with sigma of 0.1
 O40, C38, C37, C36
 with sigma of 0.1
 O107, C105, C104, C103
 with sigma of 0.1
 C113, C108, C109, O107
 with sigma of 0.1
 C112, C110, C111, O114
 with sigma of 0.1
 C112_$1, C113_$1, C108_$1, C109_$1, C110_$1, C111_$1, O107_$1, O114_$1
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
C105 \\sim C104 \\sim C103 \\sim C102 \\sim C101 \\sim C106: within 2A with
sigma of 0.002 and sigma for terminal atoms of 0.004
C46 \\sim C45 \\sim O40 \\sim C41 \\sim O54 \\sim O33 \\sim C48 \\sim C49 \\sim
C50 \\sim C51 \\sim C52 \\sim C53 \\sim C34 \\sim C39 \\sim C38 \\sim C37 \\sim
C36 \\sim C35 \\sim O47 \\sim C44 \\sim C43 \\sim C42: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
C29 \\sim C30 \\sim C31 \\sim O33: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
O54 \\sim C60 \\sim C55 \\sim C56: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C120 \\sim C123 \\sim C122 \\sim C127 \\sim O121: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08
F2 \\sim F4AA \\sim P1 \\sim F3 \\sim F5 \\sim F4 \\sim F26: within 2A with
sigma of 0.002 and sigma for terminal atoms of 0.004
F1 \\sim P2 \\sim F14 \\sim F17 \\sim F18 \\sim F0AA \\sim F23: within 2A with
sigma of 0.002 and sigma for terminal atoms of 0.004
C112 \\sim C113 \\sim C108 \\sim C109 \\sim C110 \\sim C111 \\sim O107 \\sim
O114: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
C112 \\sim C113 \\sim C108 \\sim C109 \\sim C110 \\sim C111 \\sim C82 \\sim C83
\\sim C84 \\sim C85 \\sim C86 \\sim C21 \\sim C26 \\sim C25 \\sim C24 \\sim C23
\\sim C118 \\sim C120 \\sim C66 \\sim C64 \\sim C63 \\sim C62 \\sim C61 \\sim
C46 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C88 \\sim C70 \\sim
C69 \\sim C68 \\sim C67 \\sim C71 \\sim C15 \\sim C16 \\sim C18 \\sim C19 \\sim
C20 \\sim C95 \\sim C100 \\sim C99 \\sim C98 \\sim C97 \\sim C92 \\sim C94
\\sim C89 \\sim C90 \\sim C91 \\sim C145 \\sim C144 \\sim C143 \\sim C142 \\sim
C141 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C138 \\sim C137 \\sim
C136 \\sim C135 \\sim C140 \\sim C74 \\sim C78 \\sim C77 \\sim C76 \\sim C75
\\sim C80 \\sim C73 \\sim C13 \\sim C129 \\sim C130 \\sim C131 \\sim C132 \\sim
C133 \\sim C134 \\sim C87 \\sim C105 \\sim C104 \\sim C103 \\sim C102 \\sim
C101 \\sim C106 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32
\\sim C45 \\sim C41 \\sim C14 \\sim C117 \\sim C146 \\sim C57 \\sim C58 \\sim
C59 \\sim C60 \\sim C55 \\sim C56 \\sim C119 \\sim C48 \\sim C49 \\sim C50
\\sim C51 \\sim C52 \\sim C53 \\sim C147 \\sim C34 \\sim C39 \\sim C38 \\sim
C37 \\sim C36 \\sim C35 \\sim C115 \\sim C125 \\sim C124 \\sim C123 \\sim C122
\\sim C127 \\sim C126 \\sim C44 \\sim C43 \\sim C42 \\sim C116: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
O107 \\sim C104: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
4. Rigid body (RIGU) restrains
 C118, C120, C117, C119, C115, O121, C116
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Uiso(C112)=Uiso(C113)=Uiso(C108)=Uiso(C109)=Uiso(C110)=Uiso(C111)=Uiso(O107)=
 Uiso(O114)=FVAR(1)
 Fixed Sof: F1(0.33333) P2(0.33333) F14(0.33333) F17(0.33333) F18(0.33333)
 F0AA(0.33333) F23(0.33333)
6.a Fitted hexagon refined as free rotating group:
 C112(C113,C108,C109,C110,C111), C82(C83,C84,C85,C86,N81), C21(C26,C25,C24,C23,
 N22), C66(N65,C64,C63,C62,C61), N7(C8,C9,C10,C11,C12), C70(C69,C68,C67,N72,
 C71), C15(C16,N17,C18,C19,C20), N96(C95,C100,C99,C98,C97), C92(N93,C94,C89,C90,
 C91), N0AA(C145,C144,C143,C142,C141), N1(C2,C3,C4,C5,C6), C138(C137,C136,C135,
 C140,N139), C78(C77,C76,C75,C80,N79), C129(C130,C131,C132,C133,C134),
 C105(C104,C103,C102,C101,C106), C27(C28,C29,C30,C31,C32), C57(C58,C59,C60,C55,
 C56), C48(C49,C50,C51,C52,C53), C34(C39,C38,C37,C36,C35), C125(C124,C123,C122,
 C127,C126)
;
_shelx_res_checksum              27117
_shelx_hkl_checksum              24257
_shelx_fab_checksum              70017