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_7150923
_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         'C19 H22 N2 O7'
_chemical_formula_sum            'C19 H22 N2 O7'
_chemical_formula_weight         390.39
_chemical_name_common
;
11-Hydroxy-4,5-dimethyl-8,13-diaza-
tricyclo(7.3.1.02,7)trideca-2(7),3,5,10-tetraene-8,13-tricarboxylic
acid trimethyl ester
;
_chemical_name_systematic
;
11-Hydroxy-4,5-dimethyl-8,13-diaza-tricyclo[7.3.1.02,7]trideca-2(7),3,5,10-
tetraene-8,13-tricarboxylic acid trimethyl ester
;
_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_method           SHELXL-97
_cell_angle_alpha                103.88(3)
_cell_angle_beta                 96.73(3)
_cell_angle_gamma                105.83(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1758(16)
_cell_length_b                   8.9304(18)
_cell_length_c                   13.714(3)
_cell_measurement_reflns_used    5006
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      62.672
_cell_measurement_theta_min      4.950
_cell_volume                     917.1(4)
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_collection       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997), DIAMOND v3.0a (Brandenburg, 2005)
;
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20522
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0368P)^2^+0.6087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1098
_reflns_number_gt                3601
_reflns_number_total             4169
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b803141j.txt
_cod_data_source_block           avkv11
_cod_original_cell_volume        917.1(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150923