# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Sotelo, Eddy' _publ_contact_author_email eddy.sotelo@usc.es _publ_section_title ; Convergent Assembly of Structurally Diverse Quinazolines ; loop_ _publ_author_name E.Sotelo A.Crespo F.Fernandez H.Novoa A.Coelho data_ifix4 _database_code_depnum_ccdc_archive 'CCDC 781796' _audit_creation_date 2007-02-13T14:27:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2,5-dichloro-8-formyl-4(4-methoxyphenyl)quinazoline ; _chemical_formula_moiety 'C15 H10 Cl2 N2 O1' _chemical_formula_sum 'C16 H10 Cl2 N2 O2' _chemical_formula_weight 333.16 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.753(5) _cell_length_b 8.285(5) _cell_length_c 11.930(5) _cell_angle_alpha 84.628(5) _cell_angle_beta 76.938(5) _cell_angle_gamma 84.323(5) _cell_volume 740.8(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 7.1545 _cell_measurement_theta_max 12.6245 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'dark yellow' _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.446 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_unetI/netI 0.0489 _diffrn_reflns_number 4890 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3396 _reflns_number_gt 2223 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection Dif4 _computing_cell_refinement Dif4 _computing_data_reduction Dif4 _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _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^)+(0.0529P)^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 3396 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.107 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.304 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # 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 0.0033 0.0016 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 Cl1 Cl 0.52975(8) -0.29605(7) 0.67543(5) 0.05681(19) Uani 1 1 d . . . Cl2 Cl 1.03393(10) -0.01143(9) 0.15099(5) 0.0719(2) Uani 1 1 d . . . N3 N 0.6744(2) -0.0370(2) 0.57479(13) 0.0399(4) Uani 1 1 d . . . N4 N 0.6485(2) -0.24363(19) 0.45472(14) 0.0415(4) Uani 1 1 d . . . O5 O 0.6983(3) -0.4083(2) -0.05615(13) 0.0696(5) Uani 1 1 d . . . C6 C 0.8349(3) 0.1952(2) 0.49883(17) 0.0403(5) Uani 1 1 d . . . O7 O 0.8565(3) 0.3745(2) 0.63674(15) 0.0726(5) Uani 1 1 d . . . C8 C 0.8152(3) -0.0163(2) 0.36987(16) 0.0365(4) Uani 1 1 d . . . C9 C 1.0029(3) 0.2086(3) 0.30175(18) 0.0473(5) Uani 1 1 d . . . H9 H 1.0825 0.2615 0.243 0.059 Uiso 1 1 calc R . . C10 C 0.7715(3) 0.0467(2) 0.48066(16) 0.0364(4) Uani 1 1 d . . . C11 C 0.7316(3) -0.1601(2) 0.36066(16) 0.0388(5) Uani 1 1 d . . . C12 C 0.7061(3) -0.3575(3) 0.04803(18) 0.0498(6) Uani 1 1 d . . . C13 C 0.7233(3) -0.2254(2) 0.25093(16) 0.0402(5) Uani 1 1 d . . . C14 C 0.6321(3) -0.1774(2) 0.55549(16) 0.0395(5) Uani 1 1 d . . . C15 C 0.9398(3) 0.0673(3) 0.28286(16) 0.0431(5) Uani 1 1 d . . . C16 C 0.9475(3) 0.2736(2) 0.40945(18) 0.0454(5) Uani 1 1 d . . . H16 H 0.9879 0.3716 0.4206 0.057 Uiso 1 1 calc R . . C17 C 0.6643(3) -0.1287(3) 0.16324(18) 0.0499(6) Uani 1 1 d . . . H17 H 0.6312 -0.0189 0.1722 0.062 Uiso 1 1 calc R . . C18 C 0.7663(3) -0.3891(2) 0.23665(18) 0.0476(5) Uani 1 1 d . . . H18 H 0.8 -0.4561 0.2963 0.059 Uiso 1 1 calc R . . C19 C 0.7604(3) -0.4558(3) 0.13538(19) 0.0518(6) Uani 1 1 d . . . H19 H 0.7928 -0.5657 0.1265 0.065 Uiso 1 1 calc R . . C20 C 0.6543(3) -0.1941(3) 0.06310(19) 0.0544(6) Uani 1 1 d . . . H20 H 0.6129 -0.1288 0.0055 0.068 Uiso 1 1 calc R . . C21 C 0.7846(3) 0.2647(3) 0.61337(19) 0.0531(6) Uani 1 1 d . . . H21 H 0.6935 0.2212 0.6691 0.066 Uiso 1 1 calc R . . C22 C 0.7439(4) -0.5765(4) -0.0746(2) 0.0789(9) Uani 1 1 d . . . H22A H 0.8628 -0.6059 -0.065 0.118 Uiso 1 1 calc R . . H22B H 0.7363 -0.5956 -0.1515 0.118 Uiso 1 1 calc R . . H22C H 0.663 -0.6411 -0.0199 0.118 Uiso 1 1 calc R . . 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 Cl1 0.0637(4) 0.0545(3) 0.0454(3) 0.0096(2) 0.0004(3) -0.0132(3) Cl2 0.0774(5) 0.0865(5) 0.0465(3) -0.0187(3) 0.0155(3) -0.0355(4) N3 0.0403(10) 0.0415(9) 0.0380(8) -0.0030(7) -0.0082(7) -0.0044(8) N4 0.0436(10) 0.0380(9) 0.0421(9) -0.0007(7) -0.0063(8) -0.0089(8) O5 0.0812(14) 0.0872(13) 0.0441(8) -0.0216(8) -0.0083(9) -0.0214(11) C6 0.0391(12) 0.0405(11) 0.0431(10) -0.0049(8) -0.0128(9) -0.0020(9) O7 0.0919(15) 0.0651(11) 0.0674(11) -0.0268(9) -0.0147(10) -0.0246(10) C8 0.0347(11) 0.0364(10) 0.0378(10) -0.0019(8) -0.0067(8) -0.0039(8) C9 0.0478(13) 0.0469(12) 0.0477(12) 0.0046(9) -0.0098(10) -0.0147(10) C10 0.0335(11) 0.0368(10) 0.0384(10) -0.0030(8) -0.0075(8) -0.0009(8) C11 0.0370(11) 0.0366(10) 0.0411(10) -0.0033(8) -0.0051(9) -0.0027(9) C12 0.0460(13) 0.0650(15) 0.0393(11) -0.0110(10) -0.0026(10) -0.0175(11) C13 0.0416(12) 0.0399(11) 0.0389(10) -0.0056(8) -0.0041(9) -0.0110(9) C14 0.0354(11) 0.0426(11) 0.0376(10) 0.0032(8) -0.0050(9) -0.0017(9) C15 0.0445(13) 0.0473(12) 0.0362(10) -0.0018(8) -0.0044(9) -0.0090(10) C16 0.0478(13) 0.0382(11) 0.0534(12) -0.0033(9) -0.0147(10) -0.0110(10) C17 0.0609(15) 0.0415(12) 0.0476(12) -0.0030(9) -0.0119(11) -0.0062(11) C18 0.0558(14) 0.0423(12) 0.0462(11) -0.0037(9) -0.0122(11) -0.0086(11) C19 0.0566(15) 0.0436(12) 0.0544(13) -0.0143(10) -0.0043(11) -0.0086(11) C20 0.0626(16) 0.0592(14) 0.0433(11) 0.0036(10) -0.0167(11) -0.0100(12) C21 0.0577(15) 0.0506(13) 0.0527(13) -0.0158(10) -0.0097(11) -0.0064(12) C22 0.0710(19) 0.100(2) 0.0702(17) -0.0499(16) -0.0032(15) -0.0181(17) #----------------------------------------------------------------------------# # 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 Cl1 C14 1.738(2) . ? Cl2 C15 1.736(2) . ? N3 C14 1.294(3) . ? N3 C10 1.373(2) . ? N4 C11 1.330(2) . ? N4 C14 1.343(3) . ? O5 C12 1.365(3) . ? O5 C22 1.428(3) . ? C6 C16 1.372(3) . ? C6 C10 1.421(3) . ? C6 C21 1.488(3) . ? O7 C21 1.197(3) . ? C8 C10 1.423(3) . ? C8 C15 1.427(3) . ? C8 C11 1.436(3) . ? C9 C15 1.368(3) . ? C9 C16 1.400(3) . ? C11 C13 1.479(3) . ? C12 C19 1.378(3) . ? C12 C20 1.389(3) . ? C13 C18 1.381(3) . ? C13 C17 1.390(3) . ? C17 C20 1.377(3) . ? C18 C19 1.386(3) . ? 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 C14 N3 C10 115.08(16) . . ? C11 N4 C14 116.53(17) . . ? C12 O5 C22 117.8(2) . . ? C16 C6 C10 119.12(18) . . ? C16 C6 C21 119.65(19) . . ? C10 C6 C21 121.22(18) . . ? C10 C8 C15 116.54(17) . . ? C10 C8 C11 115.49(17) . . ? C15 C8 C11 127.93(17) . . ? C15 C9 C16 120.02(19) . . ? N3 C10 C6 117.53(17) . . ? N3 C10 C8 121.46(18) . . ? C6 C10 C8 120.93(17) . . ? N4 C11 C8 120.62(17) . . ? N4 C11 C13 114.38(17) . . ? C8 C11 C13 124.97(17) . . ? O5 C12 C19 124.6(2) . . ? O5 C12 C20 115.5(2) . . ? C19 C12 C20 119.9(2) . . ? C18 C13 C17 118.41(19) . . ? C18 C13 C11 119.44(19) . . ? C17 C13 C11 122.07(19) . . ? N3 C14 N4 129.36(17) . . ? N3 C14 Cl1 116.35(15) . . ? N4 C14 Cl1 114.22(15) . . ? C9 C15 C8 121.85(18) . . ? C9 C15 Cl2 115.75(16) . . ? C8 C15 Cl2 122.21(16) . . ? C6 C16 C9 121.21(19) . . ? C20 C17 C13 120.6(2) . . ? C13 C18 C19 121.5(2) . . ? C12 C19 C18 119.3(2) . . ? C17 C20 C12 120.1(2) . . ? O7 C21 C6 122.7(2) . . ? #END _chemical_name_common 2,5-dichloro-8-formyl-4(4-methoxyphenyl)quinazoline