Stereoselective tetrapyrido[2,1-a]isoindolone synthesis via carbanionic and radical intermediates: a model study for the Tacaman alkaloid D/E ring fusionElectronic supplementary information (ESI) available: Experimental details for compounds 21?23. See http://www.rsc.org/suppdata/ob/b3/b303031h/
Hunter, Roger; Richards, Philip; Organic & Biomolecular Chemistry 1 (2003) 2348–; doi:10.1039/b303031h

data_7151431
_publ_section_title
;
 Stereoselective tetrapyrido[2,1-a]isoindolone synthesis via
 carbanionic and radical intermediates: a model study for the Tacaman
 alkaloid D/E ring fusionElectronic supplementary information (ESI)
 available: Experimental details for compounds 21?23. See
 http://www.rsc.org/suppdata/ob/b3/b303031h/
;
_journal_issue                   13
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              2348
_journal_paper_doi               10.1039/b303031h
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C14 H13 N1 O4'
_chemical_formula_sum            'C14 H13 N O4'
_chemical_formula_weight         259.08
_chemical_melting_point          'Mp decomposes >140C'
_chemical_name_common
;
(3aS,11bS,11cR)-3a,4,5,11c-Tetrahydro-10b-hydroxy-furo-(3',2':3,4)
pyrido(2,1-a)isoindol-2(1H),7(11bH)-dione
;
_chemical_name_systematic
;
(3aS,11bS,11cR)-3a,4,5,11c-Tetrahydro-10b-hydroxy-furo-[3',2' :3,4]
pyrido[2,1-a]isoindol-2(1H),7(11bH)-dione
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 100.634(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.375(1)
_cell_length_b                   7.653(1)
_cell_length_c                   9.691(1)
_cell_measurement_temperature    173(2)
_cell_volume                     610.47(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'NOnius Kappa CCD'
_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  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3358
_diffrn_reflns_theta_full        27.39
_diffrn_reflns_theta_max         27.39
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.9624
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(8)
_refine_ls_extinction_coef       0.033(4)
_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   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2511
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.280
_refine_ls_shift/su_mean         0.018
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+0.1067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0701
_reflns_number_gt                2318
_reflns_number_total             2511
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b303031h.txt
_cod_data_source_block           compound1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

2018-01-21
Z value changed to be consistent with given formula
                 miguel
;
_cod_original_formula_units_Z            4
_cod_original_cell_volume        610.5(1)
_cod_original_sg_symbol_H-M      P2(1)
_cod_original_formula_sum        'C14 H13 N1 O4'
_cod_database_code               7151431