# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Niu, Hongying' 'Xia, Chao' 'Qu, Guirong' 'Zhang, Qian' 'Jiang, Yi' 'Mao, Runze' 'Li, Deyang' 'Guo, Haiming' _publ_contact_author_name 'Guo, Haiming' _publ_contact_author_email guohm518@hotmail.com _publ_section_title ; CuBr Catalyzed C-N Cross Coupling Reaction of Purines and Diaryliodonium Salts to 9-Arylpurines ; # Attachment 'A.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 825895' #TrackingRef 'A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H5 Cl3 N4' _chemical_formula_weight 299.54 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 0.0000 0.0000 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3206(10) _cell_length_b 19.054(3) _cell_length_c 8.7032(12) _cell_angle_alpha 90.00 _cell_angle_beta 99.593(2) _cell_angle_gamma 90.00 _cell_volume 1197.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3266 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 26.96 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.749 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7795 _exptl_absorpt_correction_T_max 0.8290 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7666 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2228 _reflns_number_gt 1909 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0722P)^2^+0.9904P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2228 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.1353 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 C1 C 0.0726(4) 0.75375(16) 0.2369(4) 0.0508(7) Uani 1 1 d . . . C2 C 0.1421(4) 0.86372(15) 0.2061(3) 0.0395(6) Uani 1 1 d . . . C3 C 0.1237(4) 0.85543(15) 0.0441(3) 0.0427(6) Uani 1 1 d . . . C4 C 0.0757(4) 0.78871(18) -0.0103(4) 0.0503(7) Uani 1 1 d . . . C5 C 0.1947(4) 0.96130(16) 0.0894(3) 0.0477(7) Uani 1 1 d . . . H5 H 0.2243 1.0081 0.0756 0.057 Uiso 1 1 calc R . . C6 C 0.2193(4) 0.97027(14) 0.3788(3) 0.0367(6) Uani 1 1 d . . . C7 C 0.1612(4) 1.03952(15) 0.3812(3) 0.0409(6) Uani 1 1 d . . . H7 H 0.0988 1.0605 0.2911 0.049 Uiso 1 1 calc R . . C8 C 0.1969(4) 1.07695(15) 0.5186(3) 0.0431(7) Uani 1 1 d . . . H8 H 0.1617 1.1238 0.5215 0.052 Uiso 1 1 calc R . . C9 C 0.2852(4) 1.04413(15) 0.6515(3) 0.0404(6) Uani 1 1 d . . . C10 C 0.3386(4) 0.97482(16) 0.6507(3) 0.0429(7) Uani 1 1 d . . . H10 H 0.3952 0.9534 0.7424 0.051 Uiso 1 1 calc R . . C11 C 0.3077(4) 0.93731(15) 0.5133(3) 0.0410(6) Uani 1 1 d . . . H11 H 0.3453 0.8908 0.5107 0.049 Uiso 1 1 calc R . . Cl1 Cl 0.04188(16) 0.68474(5) 0.35993(12) 0.0777(4) Uani 1 1 d . . . Cl2 Cl 0.04685(14) 0.77010(6) -0.20633(11) 0.0723(3) Uani 1 1 d . . . Cl3 Cl 0.32771(12) 1.09137(4) 0.82548(9) 0.0584(3) Uani 1 1 d . . . N1 N 0.1153(3) 0.81413(13) 0.3076(3) 0.0445(6) Uani 1 1 d . . . N2 N 0.0509(4) 0.73699(14) 0.0859(3) 0.0545(7) Uani 1 1 d . . . N3 N 0.1872(3) 0.93312(12) 0.2342(3) 0.0400(5) Uani 1 1 d . . . N4 N 0.1574(4) 0.91770(14) -0.0265(3) 0.0512(6) Uani 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 C1 0.0539(18) 0.0392(16) 0.0576(19) 0.0035(14) 0.0040(14) -0.0016(13) C2 0.0411(14) 0.0387(14) 0.0395(15) 0.0015(11) 0.0091(11) 0.0048(11) C3 0.0433(15) 0.0457(16) 0.0392(15) 0.0003(12) 0.0075(12) 0.0053(12) C4 0.0484(17) 0.0535(18) 0.0473(17) -0.0095(15) 0.0033(13) 0.0046(14) C5 0.0639(19) 0.0414(16) 0.0395(16) 0.0065(13) 0.0137(14) 0.0010(14) C6 0.0386(14) 0.0372(14) 0.0354(14) 0.0025(11) 0.0096(11) -0.0022(11) C7 0.0442(15) 0.0398(15) 0.0390(15) 0.0080(12) 0.0082(12) 0.0034(12) C8 0.0485(16) 0.0378(15) 0.0440(16) 0.0013(12) 0.0108(12) 0.0037(12) C9 0.0419(15) 0.0422(15) 0.0380(15) -0.0007(12) 0.0088(12) -0.0052(11) C10 0.0438(15) 0.0455(16) 0.0378(15) 0.0076(12) 0.0020(12) -0.0012(12) C11 0.0441(15) 0.0362(14) 0.0429(15) 0.0061(12) 0.0078(12) 0.0004(12) Cl1 0.1050(8) 0.0465(5) 0.0784(7) 0.0153(4) 0.0061(6) -0.0173(5) Cl2 0.0836(7) 0.0812(7) 0.0509(5) -0.0229(4) 0.0077(4) -0.0057(5) Cl3 0.0728(6) 0.0577(5) 0.0434(5) -0.0089(4) 0.0056(4) -0.0052(4) N1 0.0472(13) 0.0409(14) 0.0450(14) 0.0050(11) 0.0066(11) 0.0003(10) N2 0.0566(16) 0.0459(15) 0.0584(17) -0.0054(13) 0.0015(13) -0.0025(12) N3 0.0471(13) 0.0373(12) 0.0355(12) 0.0028(10) 0.0071(10) 0.0013(10) N4 0.0639(17) 0.0525(16) 0.0381(14) 0.0039(11) 0.0110(12) 0.0028(12) _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 C1 N1 1.318(4) . ? C1 N2 1.335(4) . ? C1 Cl1 1.734(3) . ? C2 N1 1.330(4) . ? C2 N3 1.375(4) . ? C2 C3 1.403(4) . ? C3 N4 1.377(4) . ? C3 C4 1.382(4) . ? C4 N2 1.325(4) . ? C4 Cl2 1.721(3) . ? C5 N4 1.300(4) . ? C5 N3 1.379(4) . ? C5 H5 0.9300 . ? C6 C7 1.387(4) . ? C6 C11 1.389(4) . ? C6 N3 1.429(3) . ? C7 C8 1.379(4) . ? C7 H7 0.9300 . ? C8 C9 1.378(4) . ? C8 H8 0.9300 . ? C9 C10 1.378(4) . ? C9 Cl3 1.744(3) . ? C10 C11 1.379(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? 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 C1 N2 130.4(3) . . ? N1 C1 Cl1 114.7(3) . . ? N2 C1 Cl1 114.8(2) . . ? N1 C2 N3 128.5(3) . . ? N1 C2 C3 126.0(3) . . ? N3 C2 C3 105.5(2) . . ? N4 C3 C4 134.0(3) . . ? N4 C3 C2 110.9(3) . . ? C4 C3 C2 115.1(3) . . ? N2 C4 C3 121.4(3) . . ? N2 C4 Cl2 117.8(2) . . ? C3 C4 Cl2 120.8(3) . . ? N4 C5 N3 115.1(3) . . ? N4 C5 H5 122.4 . . ? N3 C5 H5 122.4 . . ? C7 C6 C11 121.2(3) . . ? C7 C6 N3 118.6(2) . . ? C11 C6 N3 120.2(2) . . ? C8 C7 C6 119.4(3) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C9 C8 C7 119.2(3) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C10 C9 C8 121.6(3) . . ? C10 C9 Cl3 119.3(2) . . ? C8 C9 Cl3 119.0(2) . . ? C9 C10 C11 119.7(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C6 118.8(3) . . ? C10 C11 H11 120.6 . . ? C6 C11 H11 120.6 . . ? C1 N1 C2 111.1(3) . . ? C4 N2 C1 115.9(3) . . ? C2 N3 C5 104.9(2) . . ? C2 N3 C6 129.2(2) . . ? C5 N3 C6 125.9(2) . . ? C5 N4 C3 103.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N4 178.6(3) . . . . ? N3 C2 C3 N4 0.3(3) . . . . ? N1 C2 C3 C4 -0.9(4) . . . . ? N3 C2 C3 C4 -179.2(3) . . . . ? N4 C3 C4 N2 -179.9(3) . . . . ? C2 C3 C4 N2 -0.5(4) . . . . ? N4 C3 C4 Cl2 0.4(5) . . . . ? C2 C3 C4 Cl2 179.7(2) . . . . ? C11 C6 C7 C8 2.0(4) . . . . ? N3 C6 C7 C8 -177.7(2) . . . . ? C6 C7 C8 C9 -1.7(4) . . . . ? C7 C8 C9 C10 -0.1(4) . . . . ? C7 C8 C9 Cl3 -179.3(2) . . . . ? C8 C9 C10 C11 1.6(4) . . . . ? Cl3 C9 C10 C11 -179.2(2) . . . . ? C9 C10 C11 C6 -1.3(4) . . . . ? C7 C6 C11 C10 -0.5(4) . . . . ? N3 C6 C11 C10 179.2(3) . . . . ? N2 C1 N1 C2 -1.3(5) . . . . ? Cl1 C1 N1 C2 178.1(2) . . . . ? N3 C2 N1 C1 179.5(3) . . . . ? C3 C2 N1 C1 1.7(4) . . . . ? C3 C4 N2 C1 0.9(5) . . . . ? Cl2 C4 N2 C1 -179.3(2) . . . . ? N1 C1 N2 C4 0.0(5) . . . . ? Cl1 C1 N2 C4 -179.3(2) . . . . ? N1 C2 N3 C5 -178.8(3) . . . . ? C3 C2 N3 C5 -0.6(3) . . . . ? N1 C2 N3 C6 0.8(5) . . . . ? C3 C2 N3 C6 179.0(3) . . . . ? N4 C5 N3 C2 0.7(4) . . . . ? N4 C5 N3 C6 -178.9(3) . . . . ? C7 C6 N3 C2 -143.9(3) . . . . ? C11 C6 N3 C2 36.4(4) . . . . ? C7 C6 N3 C5 35.6(4) . . . . ? C11 C6 N3 C5 -144.1(3) . . . . ? N3 C5 N4 C3 -0.5(4) . . . . ? C4 C3 N4 C5 179.5(3) . . . . ? C2 C3 N4 C5 0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.429 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.063