Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_t _database_code_CSD 167808 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Al-Azmi, Amal' 'Booth, B.' 'Carpenter, Robert A.' 'Carvalho, Alice' 'Marrelec, Elodie' 'Pritchard, R.' 'Proenca, Fernanda J. R. P.' _publ_contact_author_name 'Dr B Booth' _publ_contact_author_address ; Department of Chemistry UMIST PO Box 88 Manchester M60 1QD UNITED KINGDOM ; _publ_contact_author_email 'BRIAN.BOOTH@UMIST.AC.UK' _publ_section_title ; Facile Synthesis of 6-cyano-9-sunstituted-9H-purines and their ring expansion to 8-(arylamino)-4-imino-3-methaylpyrimdino[5,4-d]pyramidines ; _audit_creation_date 2001-07-02T08:30:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H14 N6 O1' _chemical_formula_structural 'C14 H14 N6 O1' _chemical_formula_sum 'C28 H28 N12 O2' _chemical_formula_weight 564.62 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 30.542(9) _cell_length_b 12.114(2) _cell_length_c 7.3571(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2722.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 16.4 _cell_measurement_theta_max 24.1 _cell_measurement_wavelength 1.54178 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.767 _exptl_absorpt_correction_T_min 0.7751 _exptl_absorpt_correction_T_max 0.9848 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_number 4659 _diffrn_reflns_av_R_equivalents 0.1181 _diffrn_reflns_av_unetI/netI 0.1359 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.66 _diffrn_reflns_theta_max 65.17 _diffrn_reflns_theta_full 65.17 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 2317 _reflns_number_gt 1019 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0665P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2317 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1572 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1703 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.216 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.47613(12) 0.4880(3) 0.2996(6) 0.0497(10) Uani 1 1 d . . . C4 C 0.46891(12) 0.6653(3) 0.1515(5) 0.0463(9) Uani 1 1 d . . . C4A C 0.51541(11) 0.6526(3) 0.1121(5) 0.0467(9) Uani 1 1 d . . . C6 C 0.57746(13) 0.7184(3) -0.0112(7) 0.0577(12) Uani 1 1 d . . . C8 C 0.58238(12) 0.5527(3) 0.1341(6) 0.0483(9) Uani 1 1 d . . . C8A C 0.53729(11) 0.5600(3) 0.1735(5) 0.0450(10) Uani 1 1 d . . . C9 C 0.40376(13) 0.5775(4) 0.2903(8) 0.0581(12) Uani 1 1 d . . . C12 C 0.64980(11) 0.4355(3) 0.1879(6) 0.0525(10) Uani 1 1 d . . . C13 C 0.68184(14) 0.4965(4) 0.0999(7) 0.0709(14) Uani 1 1 d . . . C14 C 0.72501(14) 0.4626(4) 0.1043(8) 0.0746(14) Uani 1 1 d . . . C15 C 0.73705(13) 0.3658(4) 0.1915(7) 0.0699(13) Uani 1 1 d . . . C16 C 0.70491(15) 0.3056(5) 0.2778(8) 0.0728(14) Uani 1 1 d . . . C17 C 0.66220(13) 0.3387(3) 0.2768(7) 0.0606(12) Uani 1 1 d . . . C19 C 0.81067(17) 0.3730(6) 0.1013(11) 0.140(3) Uani 1 1 d . . . H19A H 0.8015 0.3788 -0.0231 0.211 Uiso 1 1 calc R . . H19B H 0.8368 0.329 0.1082 0.211 Uiso 1 1 calc R . . H19C H 0.8165 0.4453 0.1486 0.211 Uiso 1 1 calc R . . O18 O 0.77843(10) 0.3245(4) 0.2008(6) 0.1095(14) Uani 1 1 d . . . N1 N 0.51698(10) 0.4754(2) 0.2686(4) 0.0510(8) Uani 1 1 d . . . N3 N 0.45046(9) 0.5744(2) 0.2442(4) 0.0489(8) Uani 1 1 d . . . N5 N 0.53564(10) 0.7354(3) 0.0176(5) 0.0533(9) Uani 1 1 d . . . N7 N 0.60325(10) 0.6328(3) 0.0425(5) 0.0561(9) Uani 1 1 d . . . N10 N 0.44397(10) 0.7466(3) 0.1095(5) 0.0575(9) Uani 1 1 d . . . N11 N 0.60486(10) 0.4632(3) 0.1944(5) 0.0539(9) Uani 1 1 d . . . H2 H 0.4572(15) 0.432(4) 0.354(7) 0.092(16) Uiso 1 1 d . . . H6 H 0.5915(13) 0.784(3) -0.076(6) 0.071(13) Uiso 1 1 d . . . H9A H 0.3848(16) 0.574(5) 0.175(8) 0.109(18) Uiso 1 1 d . . . H9B H 0.3945(15) 0.508(4) 0.357(6) 0.091(15) Uiso 1 1 d . . . H9C H 0.3948(16) 0.640(5) 0.364(8) 0.12(2) Uiso 1 1 d . . . H10 H 0.4653(13) 0.795(3) 0.049(6) 0.065(13) Uiso 1 1 d . . . H11 H 0.5892(11) 0.422(3) 0.246(5) 0.043(12) Uiso 1 1 d . . . H13 H 0.6725(15) 0.563(5) 0.047(7) 0.099(19) Uiso 1 1 d . . . H14 H 0.749(2) 0.504(5) 0.036(8) 0.13(2) Uiso 1 1 d . . . H16 H 0.7141(18) 0.242(5) 0.335(9) 0.13(2) Uiso 1 1 d . . . H17 H 0.6359(11) 0.298(3) 0.338(5) 0.054(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.051(2) 0.041(2) 0.056(3) -0.001(2) 0.0007(19) -0.0021(18) C4 0.057(2) 0.041(2) 0.041(2) -0.0014(19) -0.0027(18) -0.0017(18) C4A 0.052(2) 0.045(2) 0.043(2) -0.006(2) 0.0022(18) 0.0010(17) C6 0.060(3) 0.051(3) 0.062(3) 0.003(2) 0.004(2) -0.003(2) C8 0.054(2) 0.043(2) 0.048(2) 0.000(2) -0.0027(18) 0.0010(18) C8A 0.049(2) 0.039(2) 0.047(2) -0.0054(19) -0.0018(17) 0.0007(16) C9 0.053(2) 0.058(3) 0.063(3) -0.001(3) 0.008(2) 0.000(2) C12 0.050(2) 0.059(2) 0.049(2) -0.002(2) -0.0026(19) 0.0029(18) C13 0.050(2) 0.077(3) 0.085(4) 0.016(3) 0.003(2) 0.004(2) C14 0.054(2) 0.088(3) 0.082(4) 0.014(3) 0.008(2) -0.002(2) C15 0.049(2) 0.085(3) 0.075(3) 0.001(3) 0.000(2) 0.010(2) C16 0.065(3) 0.075(3) 0.079(4) 0.011(3) -0.003(3) 0.012(3) C17 0.054(2) 0.057(3) 0.071(3) 0.004(3) 0.001(2) 0.006(2) C19 0.061(3) 0.182(7) 0.177(8) 0.014(6) 0.006(4) 0.020(4) O18 0.0534(18) 0.147(3) 0.128(4) 0.025(3) 0.013(2) 0.016(2) N1 0.0558(17) 0.0421(19) 0.055(2) 0.0042(18) -0.0011(16) -0.0046(14) N3 0.0500(17) 0.0422(17) 0.054(2) 0.0006(17) 0.0033(15) 0.0005(14) N5 0.059(2) 0.0409(18) 0.060(2) 0.0090(18) 0.0055(16) -0.0044(16) N7 0.055(2) 0.0498(18) 0.063(2) 0.0011(19) 0.0087(17) -0.0048(16) N10 0.0578(19) 0.0482(17) 0.067(2) 0.008(2) 0.0021(18) 0.0099(18) N11 0.0479(18) 0.050(2) 0.064(2) 0.0070(19) 0.0086(17) -0.0012(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 N1 1.277(5) . ? C2 N3 1.370(5) . ? C4 N10 1.283(4) . ? C4 N3 1.413(5) . ? C4 C4A 1.458(5) . ? C4A N5 1.367(5) . ? C4A C8A 1.382(5) . ? C6 N5 1.311(5) . ? C6 N7 1.361(5) . ? C8 N7 1.343(5) . ? C8 N11 1.357(5) . ? C8 C8A 1.410(5) . ? C8A N1 1.388(5) . ? C9 N3 1.466(5) . ? C12 C13 1.386(6) . ? C12 C17 1.396(6) . ? C12 N11 1.414(5) . ? C13 C14 1.381(6) . ? C14 C15 1.387(6) . ? C15 O18 1.361(5) . ? C15 C16 1.378(7) . ? C16 C17 1.365(6) . ? C19 O18 1.360(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 N3 126.7(4) . . ? N10 C4 N3 118.6(3) . . ? N10 C4 C4A 127.7(4) . . ? N3 C4 C4A 113.7(3) . . ? N5 C4A C8A 122.9(3) . . ? N5 C4A C4 117.7(3) . . ? C8A C4A C4 119.4(3) . . ? N5 C6 N7 129.5(4) . . ? N7 C8 N11 120.1(3) . . ? N7 C8 C8A 121.4(4) . . ? N11 C8 C8A 118.5(4) . . ? C4A C8A N1 123.3(3) . . ? C4A C8A C8 117.1(3) . . ? N1 C8A C8 119.6(3) . . ? C13 C12 C17 118.3(4) . . ? C13 C12 N11 125.1(4) . . ? C17 C12 N11 116.6(4) . . ? C14 C13 C12 120.3(5) . . ? C13 C14 C15 121.0(5) . . ? O18 C15 C16 116.4(5) . . ? O18 C15 C14 125.5(4) . . ? C16 C15 C14 118.2(4) . . ? C17 C16 C15 121.5(5) . . ? C16 C17 C12 120.6(4) . . ? C19 O18 C15 119.1(5) . . ? C2 N1 C8A 116.0(3) . . ? C2 N3 C4 120.8(3) . . ? C2 N3 C9 120.5(3) . . ? C4 N3 C9 118.6(3) . . ? C6 N5 C4A 114.0(3) . . ? C8 N7 C6 115.0(3) . . ? C8 N11 C12 132.0(4) . . ?