Intramolecular Direct C-H Arylation Approach to Fused Purines. Synthesis of Purino[8,9-f]phenanthridines and 5,6-Dihydropurino[8,9-a]isoquinolines
Igor Čerňa; Radek Pohl; Blanka Klepetářová; Michal Hocek; Journal of Organic Chemistry 75 (2010) 2302–2308; doi:10.1021/jo100111t

data_4025331
_publ_contact_author_address
;Institute of Organic Chemistry and Biochemistry
Gilead Sciences & IOCHB Research Center
Academy of Sciences of the Czech Republic
Flemingovo nam. 2
16010 Prague 6
Czech Republic
;
_publ_contact_author_email       hocek@uochb.cas.cz
_publ_contact_author_fax         +420220183559
_publ_contact_author_name        'Michal Hocek'
_publ_contact_author_phone       +420220183324
_publ_section_title
;
 Intramolecular Direct C-H Arylation Approach to Fused Purines. Synthesis
 of Purino[8,9-f]phenanthridines and 5,6-Dihydropurino[8,9-a]isoquinolines
;
_journal_issue                   7
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2302
_journal_page_last               2308
_journal_paper_doi               10.1021/jo100111t
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C13 H11 N5'
_chemical_formula_sum            'C13 H11 N5'
_chemical_formula_weight         237.26
_chemical_name_systematic
'11-amino-5,6-dihydropurino[8,9-a]isoquinoline '
_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
_cell_angle_alpha                103.269(7)
_cell_angle_beta                 93.029(6)
_cell_angle_gamma                91.387(7)
_cell_formula_units_Z            4
_cell_length_a                   7.3513(6)
_cell_length_b                   10.8273(10)
_cell_length_c                   13.9340(10)
_cell_measurement_reflns_used    12021
_cell_measurement_temperature    150
_cell_measurement_theta_max      77
_cell_measurement_theta_min      4
_cell_volume                     1077.20(16)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35870
_diffrn_reflns_theta_full        74.114
_diffrn_reflns_theta_max         78.015
_diffrn_reflns_theta_min         4.198
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.26
_refine_ls_extinction_coef       7.4(12)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0786
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.0002957
_refine_ls_shift/su_mean         0.0001783
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 6.95 1.83 4.82 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0743
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0562
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3288
_reflns_number_total             4541
_reflns_threshold_expression     I>2.0\s(I)
_oxford_refine_ls_r_factor_ref   0.0497
_oxford_reflns_number_all        4523
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            jo100111t_si_003.cif
_cod_data_source_block           1
_cod_database_code               4025331