Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by cyclization of 1,3-bis(silyl enol ethers) with quinazolines
Karapetyan, Vahuni; Mkrtchyan, Satenik; Schmidt, Andreas; Gütlein, Jörg-Peter; Villinger, Alexander; Reinke, Helmut; Jiao, Haijun; Fischer, Christine; Langer, Peter; Organic & Biomolecular Chemistry 6 (2008) 2961–2968; doi:10.1039/b803141j

data_7150922
_publ_section_title
;
 Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by
 cyclization of 1,3-bis(silyl enol ethers) with quinazolines
;
_journal_issue                   16
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              2961
_journal_page_last               2968
_journal_paper_doi               10.1039/b803141j
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C20 H22 N2 O7'
_chemical_formula_sum            'C20 H22 N2 O7'
_chemical_formula_weight         402.40
_chemical_melting_point          371
_chemical_name_common
;
11-Hydroxy-4,5(1',3')-propylene-8,13-diaza-
tricyclo(7.3.1.0$2,7!)trideca-2(7),3,5,10-tetraene-8,10,13-
tricarboxylic acid trimethyl ester
;
_chemical_name_systematic
;
11-Hydroxy-4,5(1',3')-propylene-8,13-diaza-
tricyclo[7.3.1.0^2,7^]trideca-2(7),3,5,10-tetraene-8,10,13-
tricarboxylic acid trimethyl ester
;
_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                91.2360(10)
_cell_angle_beta                 98.8450(10)
_cell_angle_gamma                95.8850(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2926(2)
_cell_length_b                   8.4322(2)
_cell_length_c                   13.9059(3)
_cell_measurement_reflns_used    8603
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      39.73
_cell_measurement_theta_min      2.43
_cell_volume                     955.05(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  '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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29775
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'fragment of plate'
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.061
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         5469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0867P)^2^+0.4115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1569
_reflns_number_gt                4810
_reflns_number_total             5469
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b803141j.txt
_cod_data_source_block           kv9(5z)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P-1 '
_cod_database_code               7150922