Cycloaddition-based Formal C–H Alkynylation of Isoindoles Leading to the Synthesis of Air-stable Fluorescent 1,3-Dialkynylisoindoles
Ohmura, Toshimichi; Kijima, Akihito; Komori, Yusuke; Suginome, Michinori; Organic Letters 15 (2013) 3510–; doi:10.1021/ol401051d

data_1512164
_publ_section_title
;
 Cycloaddition-based Formal C--H Alkynylation of Isoindoles Leading to the
 Synthesis of Air-stable Fluorescent 1,3-Dialkynylisoindoles
;
_journal_issue                   14
_journal_name_full               'Organic Letters'
_journal_page_first              3510
_journal_paper_doi               10.1021/ol401051d
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C31 H49 N Si2'
_chemical_formula_weight         491.89
_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                 91.1723(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5545(6)
_cell_length_b                   14.3605(6)
_cell_length_c                   16.0482(8)
_cell_measurement_temperature    296(2)
_cell_volume                     3123.1(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'Yadokari-XG (Wakita, 2000)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_sigmaI/netI    0.0777
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29510
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_density_diffrn    1.046
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         7126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+3.7352P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1508
_reflns_number_gt                4392
_reflns_number_total             7126
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol401051d_si_003.cif
_cod_data_source_block           1
_cod_original_sg_symbol_Hall     -p_2ybc
_cod_original_sg_symbol_H-M      p_21/c
_cod_database_code               1512164