Metal-Free [3 + 2 + 1]/[2 + 2 + 1] Biscyclization: Stereospecific Construction with Concomitant Functionalization of Indolizin-5(1H)-one
Tuan-Jie Li; Zhong-Qiu Liu; Hong-Mei Yin; Chang-Sheng Yao; Bo Jiang; Xiang-Shan Wang; Shu-Jiang Tu; Xiu-Ling Li; Guigen Li; Journal of Organic Chemistry 78 (2013) 11414–11420; doi:10.1021/jo401969g

data_4028759
_publ_section_title
;
 Metal-Free [3 + 2 + 1]/[2 + 2 + 1] Biscyclization: Stereospecific
 Construction with Concomitant Functionalization of Indolizin-5(1H)-one
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11414
_journal_page_last               11420
_journal_paper_doi               10.1021/jo401969g
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C43 H34 Cl2 N4 O5'
_chemical_formula_weight         757.64
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                112.753(2)
_cell_angle_beta                 99.306(2)
_cell_angle_gamma                101.604(2)
_cell_formula_units_Z            2
_cell_length_a                   11.4634(16)
_cell_length_b                   13.4376(19)
_cell_length_c                   13.962(2)
_cell_measurement_reflns_used    7324
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.82
_cell_measurement_theta_min      2.54
_cell_volume                     1873.3(5)
_computing_cell_refinement       'SAINTPLUS(Bruker, 2003)'
_computing_data_collection       'SMART(Bruker, 2003)'
_computing_data_reduction        SAINTPLUS
_computing_molecular_graphics    'SHELXTL(Bruker, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Smart Apex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13339
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.9691
_exptl_absorpt_correction_T_min  0.9521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS(Sheldrick,2003)
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6538
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0752
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1572P)^2^+1.2283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2333
_refine_ls_wR_factor_ref         0.2546
_reflns_number_gt                5336
_reflns_number_total             6538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401969g_si_002.cif
_cod_data_source_block           1
_cod_database_code               4028759