The imidato-alkenyllithium route for the synthesis of the isoquinocycline-pyrrolopyrrole substructure.
Breuning, M André; Harms, Klaus; Koert, Ulrich; Organic letters 13 (2011) 1402–1405; doi:10.1021/ol200085g

data_1502022
_publ_section_title
;
 The imidato-alkenyllithium route for the synthesis of the
 isoquinocycline-pyrrolopyrrole substructure.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1402
_journal_page_last               1405
_journal_paper_doi               10.1021/ol200085g
_journal_volume                  13
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C31 H40 N2 O5 S Si, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C33 H44 N2 O6 S Si'
_chemical_formula_weight         624.85
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-01-11T14:22:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                79.724(6)
_cell_angle_beta                 89.131(6)
_cell_angle_gamma                71.349(5)
_cell_formula_units_Z            2
_cell_length_a                   10.6719(7)
_cell_length_b                   12.0517(8)
_cell_length_c                   13.6594(10)
_cell_measurement_reflns_used    16455
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4.5
_cell_measurement_wavelength     0.71073
_cell_volume                     1636.2(2)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-AREA'
_computing_molecular_graphics    'DIAMOND 3.2'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16685
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         4.64
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.0003
_exptl_absorpt_correction_T_min  0.9089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'c.f. R.H. Blessing, Acta Cryst. (1995), A51, 33-38'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0068(17)
_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   1.044
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         5729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+0.2055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                4707
_reflns_number_total             5729
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol200085g_si_002.cif
_cod_data_source_block           mab1014
_cod_original_cell_volume        1636.19(19)
_cod_database_code               1502022