Facile synthesis of 6-cyano-9-substituted-9H-purines and their ring expansion to 8-(arylamino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidines
Al-Azmi, Amal; Booth, Brian L.; Carpenter, Robert A.; Carvalho, Alice; Marrelec, Elodie; Pritchard, Robin G.; ProenÃ§a, M. Fernanda J. R. P.; Journal of the Chemical Society, Perkin Transactions 1  (2001) 2532–; doi:10.1039/b106539b

data_7216893
_publ_section_title
;
 Facile synthesis of 6-cyano-9-substituted-9H-purines and their ring
 expansion to 8-(arylamino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidines
;
_journal_issue                   20
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2532
_journal_paper_doi               10.1039/b106539b
_journal_year                    2001
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H14 N6 O1'
_chemical_formula_structural     'C14 H14 N6 O1'
_chemical_formula_sum            'C14 H14 N6 O'
_chemical_formula_weight         282.31
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_date             2001-07-02T08:30:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.542(9)
_cell_length_b                   12.114(2)
_cell_length_c                   7.3571(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.1
_cell_measurement_theta_min      16.4
_cell_measurement_wavelength     1.54178
_cell_volume                     2722.0(10)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1181
_diffrn_reflns_av_unetI/netI     0.1359
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4659
_diffrn_reflns_theta_full        65.17
_diffrn_reflns_theta_max         65.17
_diffrn_reflns_theta_min         4.66
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.7751
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1572
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0665P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1703
_reflns_number_gt                1019
_reflns_number_total             2317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b106539b.txt
_cod_data_source_block           t
_cod_depositor_comments
;

2018-03-13
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2722.1(10)
_cod_original_formula_sum        'C28 H28 N12 O2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     564.62
_cod_database_code               7216893