Copper-Catalyzed Reaction of α-Aryldiazoesters with Terminal Alkynes: A Formal [3 + 2] Cycloaddition Route Leading to Indene Derivatives
Eun Ju Park; Seok Hwan Kim; Sukbok Chang; Journal of the American Chemical Society 130 (2008) 17268–17269; doi:10.1021/ja808080h

data_4108907
_publ_section_title
;
 Copper-Catalyzed Reaction of \a-Aryldiazoesters with Terminal Alkynes: A
 Formal [3 + 2] Cycloaddition Route Leading to Indene Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17268
_journal_page_last               17269
_journal_paper_doi               10.1021/ja808080h
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C21 H15 Br O2'
_chemical_formula_weight         379.24
_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                 104.200(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.181(2)
_cell_length_b                   5.5982(10)
_cell_length_c                   23.583(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1687.0(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13108
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    2.446
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_F_000             768
_refine_diff_density_max         1.003
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.242
_refine_ls_shift/su_mean         0.030
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1171P)^2^+3.2781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1931
_refine_ls_wR_factor_ref         0.2363
_reflns_number_gt                1747
_reflns_number_total             2957
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja808080h_si_002.cif
_cod_data_source_block           sbc37
_cod_database_code               4108907