Catalytic "Active-Metal" Template Synthesis of [2]Rotaxanes, [3]Rotaxanes, and Molecular Shuttles, and Some Observations on the Mechanism of the Cu(I)-Catalyzed Azide-Alkyne 1,3-Cycloaddition
Vincent Aucagne; José Berná; James D. Crowley; Stephen M. Goldup; Kevin D. Hänni; David A. Leigh; Paul J. Lusby; Vicki E. Ronaldson; Alexandra M. Z. Slawin; Aurélien Viterisi; D. Barney Walker; Journal of the American Chemical Society 129 (2007) 11950–11963; doi:10.1021/ja073513f

data_4109958
_publ_contact_author_address
;School of Chemistry
University of Edinburgh
The King's Buildings
West Mains Road
Edinburgh
United Kingdom
;
_publ_contact_author_email       'David.Leigh@ed.ac.uk '
_publ_contact_author_fax         '+44 131 650 6453'
_publ_contact_author_name        'David A. Leigh'
_publ_contact_author_phone       '+44 131 650 4721'
_publ_section_title
;
 Catalytic "Active-Metal" Template Synthesis of [2]Rotaxanes,
 [3]Rotaxanes, and Molecular Shuttles, and Some Observations on the
 Mechanism of the Cu(I)-Catalyzed Azide-Alkyne 1,3-Cycloaddition
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11950
_journal_page_last               11963
_journal_paper_doi               10.1021/ja073513f
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C80 H95 N3 O2.2(C33 H43 N O2)'
_chemical_formula_sum            'C146 H181 N5 O6'
_chemical_formula_weight         2101.96
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.390(4)
_cell_angle_beta                 73.528(4)
_cell_angle_gamma                83.845(4)
_cell_formula_units_Z            2
_cell_length_a                   14.0813(12)
_cell_length_b                   19.2182(17)
_cell_length_c                   24.208(2)
_cell_measurement_reflns_used    17179
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      62.99
_cell_measurement_theta_min      1.88
_cell_volume                     6230.4(9)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\o scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1469
_diffrn_reflns_av_sigmaI/netI    0.1038
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31202
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         44.72
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.511
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.0040
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_description       prism
_exptl_crystal_F_000             2280
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.211
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.0007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.819
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1319
_refine_ls_number_reflns         9695
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.819
_refine_ls_R_factor_all          0.2049
_refine_ls_R_factor_gt           0.1765
_refine_ls_shift/su_max          0.179
_refine_ls_shift/su_mean         0.023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4507
_refine_ls_wR_factor_ref         0.4713
_reflns_number_gt                7198
_reflns_number_total             9695
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja073513fsi20070517_034444.cif
_cod_data_source_block           dled118
_cod_original_cell_volume        6230.5(10)
_cod_database_code               4109958