Evaluation of multivalency as an organization principle for the efficient synthesis of doubly and triply threaded amide rotaxanes
Kaufmann, Lena; Traulsen, Nora L.; Springer, Andreas; Schröder, Hendrik V.; Mäkelä, Toni; Rissanen, Kari; Schalley, Christoph A.; Org. Chem. Front. 1 (2014) 521–; doi:10.1039/C4QO00077C

data_1552988
_publ_section_title
;
 Evaluation of multivalency as an organization principle for the efficient
 synthesis of doubly and triply threaded amide rotaxanes
;
_journal_issue                   5
_journal_name_full               'Org. Chem. Front.'
_journal_page_first              521
_journal_paper_doi               10.1039/C4QO00077C
_journal_volume                  1
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C59 H62 I0.5 N5 O4, 0.5(I), C17 H26 N2 O2'
_chemical_formula_sum            'C76 H88 I N7 O6'
_chemical_formula_weight         1322.43
_chemical_name_systematic        'Macrocycle + axle'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-11-06
_audit_creation_method
;
  Olex2 1.2
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.695(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   17.0807(5)
_cell_length_b                   9.5870(3)
_cell_length_c                   20.1987(6)
_cell_measurement_reflns_used    10136
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      74.9482
_cell_measurement_theta_min      3.4992
_cell_volume                     3300.72(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.9952
_diffrn_measured_fraction_theta_max 0.9952
_diffrn_measurement_details
;
  1 omega  -92.00   -2.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000   30.0000 180

  2 omega  -62.00   29.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   64.0000  -49.0000 182

  3 omega -108.00  -18.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -45.0000  -60.0000 180

  4 omega   19.00   86.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       43.8187   57.0000  -60.0000 134

  5 omega   84.00  117.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.8677   45.0000 -120.0000 66

  6 omega   39.00   99.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.8677  -45.0000  -90.0000 120

  7 omega   89.00  169.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.8677   30.0000 -180.0000 160

  8 omega   84.00  167.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.8677   45.0000  -90.0000 166

  9 omega   40.00  122.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.8677 -125.0000   90.0000 164

 10 omega   53.00   97.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.8677  -45.0000   60.0000 88

 11 omega   38.00   91.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.8677  -30.0000 -180.0000 106

 12 omega   94.00  177.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.8677  125.0000   60.0000 166

 13 omega   84.00  114.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.8677   45.0000 -150.0000 60

 14 omega  133.00  176.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.8677   45.0000 -150.0000 86

 15 omega  114.00  177.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      106.8677  125.0000 -150.0000 126
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0827328000
_diffrn_orient_matrix_UB_12      0.0550770000
_diffrn_orient_matrix_UB_13      0.0121645000
_diffrn_orient_matrix_UB_21      0.0062057000
_diffrn_orient_matrix_UB_22      0.1065547000
_diffrn_orient_matrix_UB_23      -0.0564694000
_diffrn_orient_matrix_UB_31      -0.0359212000
_diffrn_orient_matrix_UB_32      -0.1067881000
_diffrn_orient_matrix_UB_33      -0.0500799000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20126
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         3.50
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1388
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.745
_refine_diff_density_min         -1.051
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.300(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     776
_refine_ls_number_reflns         11572
_refine_ls_number_restraints     127
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.1014
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+16.1121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2315
_refine_ls_wR_factor_ref         0.2347
_reflns_number_gt                10790
_reflns_number_total             11572
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4qo00077c2.cif
_cod_data_source_block           9@1a
_cod_original_cell_volume        3300.71(17)
_cod_database_code               1552988
_chemical_oxdiff_formula         'C80 H100 N7 O8 I1'
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97