Experimental Investigation on the Mechanism of Chelation-Assisted, Copper(II) Acetate-Accelerated Azide-Alkyne Cycloaddition
Gui-Chao Kuang; Pampa M. Guha; Wendy S. Brotherton; J. Tyler Simmons; Lisa A. Stankee; Brian T. Nguyen; Ronald J. Clark; Lei Zhu; Journal of the American Chemical Society 133 (2011) 13984–14001; doi:10.1021/ja203733q

data_4106686
_publ_section_title
;
 Experimental Investigation on the Mechanism of Chelation-Assisted,
 Copper(II) Acetate-Accelerated Azide-Alkyne Cycloaddition
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13984
_journal_page_last               14001
_journal_paper_doi               10.1021/ja203733q
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C12 H18'
_chemical_formula_sum            'C12 H18'
_chemical_formula_weight         162.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.48
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8256(5)
_cell_length_b                   10.8722(5)
_cell_length_c                   11.1507(5)
_cell_measurement_reflns_used    5311
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.64
_cell_measurement_theta_min      2.78
_cell_volume                     1164.34(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      153(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12689
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.051
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.9883
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.926
_exptl_crystal_description       irregular
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.016(6)
_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   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0990P)^2^+0.2313P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1650
_refine_ls_wR_factor_ref         0.1729
_reflns_number_gt                2274
_reflns_number_total             2668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja203733q_si_006.cif
_cod_data_source_block           zhu108
_cod_original_sg_symbol_Hall     -P2ybc
_cod_database_code               4106686