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_4103026
_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         'C98 H29 Br, 1.5(C S2)'
_chemical_formula_sum            'C99.5 H29 Br S3'
_chemical_formula_weight         1400.31
_chemical_name_systematic
;
 C60Ph4CHCC6H4BrC6H3
;
_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             2009-03-25T16:48:33-00:00
_cell_angle_alpha                90
_cell_angle_beta                 129.5250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.6322(6)
_cell_length_b                   17.6805(3)
_cell_length_c                   25.6132(5)
_cell_measurement_reflns_used    67912
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      71.88
_cell_measurement_theta_min      3.00
_cell_measurement_wavelength     1.54187
_cell_volume                     12097.3(4)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            67912
_diffrn_reflns_theta_full        71.88
_diffrn_reflns_theta_max         71.88
_diffrn_reflns_theta_min         3
_exptl_absorpt_coefficient_mu    2.359
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             5672
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.921
_refine_diff_density_min         -1.611
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     920
_refine_ls_number_reflns         11668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0839
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1682P)^2^+36.3540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2623
_refine_ls_wR_factor_ref         0.269
_reflns_number_gt                10014
_reflns_number_total             11668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1056399_si_003.cif
_cod_data_source_block           annulation_alkyneBr
_cod_depositor_comments
;

2021-09-13
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C199 H58 Br2 S6'
_cod_original_formula_weight         2800.63
_cod_original_formula_moiety         'C199 H58 Br2 S6'
_cod_original_formula_units_Z            4
_cod_database_code               4103026