Copper-Catalyzed Formal [4 + 2] Annulation between Alkyne and Fullerene Bromide
Zuo Xiao; Yutaka Matsuo; Eiichi Nakamura; Journal of the American Chemical Society 132 (2010) 12234–12236; doi:10.1021/ja1056399

data_4103025
_publ_contact_author             'MATSUO, Yutaka'
_publ_contact_author_email       matsuo@chem.s.u-tokyo.ac.jp
_publ_section_title
;
 Copper-Catalyzed Formal [4 + 2] Annulation between Alkyne and Fullerene
 Bromide
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12234
_journal_page_last               12236
_journal_paper_doi               10.1021/ja1056399
_journal_volume                  132
_journal_year                    2010
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C101 H34 Cl1 O1 S2'
_chemical_formula_sum            'C101 H34 Cl O S2'
_chemical_formula_weight         1362.85
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-06-06T18:49:34-00:00
_cell_angle_alpha                90
_cell_angle_beta                 129.4760(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.7585(6)
_cell_length_b                   17.8536(4)
_cell_length_c                   25.6731(5)
_cell_measurement_reflns_used    69339
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      50.7
_cell_measurement_theta_min      2.74
_cell_measurement_wavelength     1.5418
_cell_volume                     12297.6(5)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0965
_diffrn_reflns_av_unetI/netI     0.1277
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            69339
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    1.664
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             5576
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.309
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.00006(2)
_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   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     972
_refine_ls_number_reflns         11254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0799
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1547P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2424
_refine_ls_wR_factor_ref         0.2643
_reflns_number_gt                6973
_reflns_number_total             11254
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1056399_si_002.cif
_cod_data_source_block           annulationOMe
_cod_original_cell_volume        12297.6(4)
_cod_database_code               4103025