# Supplementary Material (ESI) for PCCP # This journal is (c) the Owner Societies 2010 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Radek Marek' _publ_contact_author_email RMAREK@CHEMI.MUNI.CZ _publ_section_title ; Understanding the NMR Chemical Shifts for 6-Halopurines: Role of Structure, Solvent and Relativistic Effects ; loop_ _publ_author_name 'Radek Marek' 'Michal Hocek' 'Katerina Malinakova' 'Jaromir Marek' 'Stanislav Standara' 'Michal Straka' ; J.Vaara ; # Attachment '2a1.cif' data_rm3 _database_code_depnum_ccdc_archive 'CCDC 742758' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common 9-benzyl-6-chloropurine _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 Cl N4' _chemical_formula_sum 'C12 H9 Cl N4' _chemical_formula_weight 244.68 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 'P 21/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 4.9073(4) _cell_length_b 24.240(2) _cell_length_c 9.3569(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.236(8) _cell_angle_gamma 90.00 _cell_volume 1111.26(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5007 _cell_measurement_theta_min 3.3125 _cell_measurement_theta_max 28.7555 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.324 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 8.3611 _diffrn_measurement_device_type 'KUMA KM4 + CCD' _diffrn_measurement_method 'rotation method, \w--scan' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4868 _diffrn_reflns_av_R_equivalents 0.0779 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1927 _reflns_number_gt 1830 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0350P)^2^+4.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1927 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.1574 _refine_ls_wR_factor_gt 0.1562 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 Cl1 Cl 0.7483(2) 0.64767(4) 0.26898(10) 0.0332(3) Uani 1 1 d . . . N1 N 0.3794(6) 0.58998(13) 0.3947(3) 0.0271(7) Uani 1 1 d . . . C2 C 0.2421(7) 0.54293(16) 0.4184(3) 0.0258(8) Uani 1 1 d . . . H2 H 0.1045 0.5455 0.4856 0.031 Uiso 1 1 calc R . . N3 N 0.2736(6) 0.49335(13) 0.3603(3) 0.0229(7) Uani 1 1 d . . . C4 C 0.4677(7) 0.49390(14) 0.2647(3) 0.0188(7) Uani 1 1 d . . . C5 C 0.6204(7) 0.53970(14) 0.2267(3) 0.0191(7) Uani 1 1 d . . . C6 C 0.5682(7) 0.58794(15) 0.2994(4) 0.0236(8) Uani 1 1 d . . . N7 N 0.7987(6) 0.52570(12) 0.1231(3) 0.0210(6) Uani 1 1 d . . . C8 C 0.7529(7) 0.47321(14) 0.1030(3) 0.0202(7) Uani 1 1 d . . . H8 H 0.8477 0.4520 0.0363 0.024 Uiso 1 1 calc R . . N9 N 0.5573(5) 0.45073(12) 0.1853(3) 0.0197(6) Uani 1 1 d . . . C10 C 0.4526(7) 0.39410(15) 0.1777(4) 0.0264(8) Uani 1 1 d . . . H10A H 0.3416 0.3893 0.0869 0.032 Uiso 1 1 calc R . . H10B H 0.3319 0.3880 0.2575 0.032 Uiso 1 1 calc R . . C11 C 0.6770(7) 0.35147(14) 0.1857(4) 0.0209(7) Uani 1 1 d . . . C12 C 0.7937(8) 0.33422(15) 0.3182(4) 0.0265(8) Uani 1 1 d . . . H12 H 0.7301 0.3493 0.4040 0.032 Uiso 1 1 calc R . . C13 C 1.0007(8) 0.29542(15) 0.3253(4) 0.0288(8) Uani 1 1 d . . . H13 H 1.0787 0.2840 0.4158 0.035 Uiso 1 1 calc R . . C14 C 1.0950(8) 0.27308(15) 0.2007(4) 0.0303(8) Uani 1 1 d . . . H14 H 1.2379 0.2466 0.2057 0.036 Uiso 1 1 calc R . . C15 C 0.9795(8) 0.28965(15) 0.0690(4) 0.0289(8) Uani 1 1 d . . . H15 H 1.0421 0.2742 -0.0165 0.035 Uiso 1 1 calc R . . C16 C 0.7733(7) 0.32867(15) 0.0616(4) 0.0251(8) Uani 1 1 d . . . H16 H 0.6965 0.3400 -0.0292 0.030 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 0.0378(6) 0.0267(5) 0.0348(5) -0.0012(4) -0.0008(4) 0.0014(4) N1 0.0256(16) 0.0388(18) 0.0165(14) -0.0019(12) -0.0012(12) 0.0100(13) C2 0.0207(18) 0.044(2) 0.0132(15) 0.0012(14) 0.0038(13) 0.0114(15) N3 0.0159(14) 0.0399(18) 0.0132(13) 0.0040(12) 0.0016(11) 0.0043(12) C4 0.0141(16) 0.0290(18) 0.0130(15) 0.0026(13) -0.0017(12) 0.0029(13) C5 0.0169(16) 0.0272(17) 0.0133(15) 0.0018(13) 0.0007(12) 0.0049(13) C6 0.0235(18) 0.0295(19) 0.0173(16) 0.0023(14) -0.0043(14) 0.0064(14) N7 0.0189(15) 0.0296(16) 0.0146(13) 0.0011(11) 0.0026(11) 0.0029(12) C8 0.0177(17) 0.0278(18) 0.0153(15) 0.0014(13) 0.0030(13) 0.0016(13) N9 0.0132(13) 0.0288(15) 0.0174(13) 0.0013(11) 0.0037(11) 0.0004(11) C10 0.0196(18) 0.0281(19) 0.0318(19) 0.0004(15) 0.0028(15) -0.0004(14) C11 0.0154(17) 0.0253(18) 0.0224(17) -0.0003(13) 0.0028(13) -0.0044(13) C12 0.033(2) 0.0272(19) 0.0200(17) 0.0002(14) 0.0049(15) -0.0029(15) C13 0.032(2) 0.0260(19) 0.0278(19) 0.0048(15) 0.0000(16) -0.0006(15) C14 0.0229(19) 0.0247(18) 0.043(2) 0.0007(16) 0.0032(16) 0.0010(15) C15 0.028(2) 0.0292(19) 0.0305(19) -0.0092(15) 0.0103(16) -0.0047(15) C16 0.0239(19) 0.033(2) 0.0186(16) -0.0022(14) 0.0009(14) -0.0042(15) _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 C6 1.728(4) . ? N1 C6 1.323(5) . ? N1 C2 1.349(5) . ? C2 N3 1.332(5) . ? C2 H2 0.9500 . ? N3 C4 1.343(4) . ? C4 N9 1.370(4) . ? C4 C5 1.396(5) . ? C5 C6 1.384(5) . ? C5 N7 1.385(4) . ? N7 C8 1.304(4) . ? C8 N9 1.377(4) . ? C8 H8 0.9500 . ? N9 C10 1.466(5) . ? C10 C11 1.509(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.392(5) . ? C11 C12 1.401(5) . ? C12 C13 1.383(5) . ? C12 H12 0.9500 . ? C13 C14 1.388(6) . ? C13 H13 0.9500 . ? C14 C15 1.387(5) . ? C14 H14 0.9500 . ? C15 C16 1.384(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 C6 N1 C2 117.0(3) . . ? N3 C2 N1 128.7(3) . . ? N3 C2 H2 115.6 . . ? N1 C2 H2 115.6 . . ? C2 N3 C4 111.5(3) . . ? N3 C4 N9 128.0(3) . . ? N3 C4 C5 126.0(3) . . ? N9 C4 C5 106.0(3) . . ? C6 C5 N7 133.9(3) . . ? C6 C5 C4 115.5(3) . . ? N7 C5 C4 110.6(3) . . ? N1 C6 C5 121.3(3) . . ? N1 C6 Cl1 117.6(3) . . ? C5 C6 Cl1 121.1(3) . . ? C8 N7 C5 103.3(3) . . ? N7 C8 N9 115.2(3) . . ? N7 C8 H8 122.4 . . ? N9 C8 H8 122.4 . . ? C4 N9 C8 104.9(3) . . ? C4 N9 C10 128.2(3) . . ? C8 N9 C10 126.7(3) . . ? N9 C10 C11 112.7(3) . . ? N9 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? N9 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C16 C11 C12 118.6(3) . . ? C16 C11 C10 120.8(3) . . ? C12 C11 C10 120.6(3) . . ? C13 C12 C11 120.5(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 120.2(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.7(4) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C16 C15 C14 120.2(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 120.7(3) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.390 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.081 # Attachment 'B921383J_support2.txt' data_Compound1a _database_code_depnum_ccdc_archive 'CCDC 742759' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 7-benzyl-6-chloropurine _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 Cl N4' _chemical_formula_sum 'C12 H9 Cl N4' _chemical_formula_weight 244.68 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 'P 21/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 14.7190(14) _cell_length_b 4.9706(4) _cell_length_c 15.8872(15) _cell_angle_alpha 90.00 _cell_angle_beta 111.317(11) _cell_angle_gamma 90.00 _cell_volume 1082.82(17) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3121 _cell_measurement_theta_min 2.372 _cell_measurement_theta_max 25.7165 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.332 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 8.3611 _diffrn_measurement_device_type 'KUMA KM4 + CCD' _diffrn_measurement_method 'rotation method, \w--scan' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6502 _diffrn_reflns_av_R_equivalents 0.1018 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2118 _reflns_number_gt 1834 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary constr _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2118 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1509 _refine_ls_wR_factor_gt 0.1432 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.62584(4) 0.88122(10) 0.51856(3) 0.0269(2) Uani 1 1 d . . . N1 N 0.79822(13) 0.9925(4) 0.51532(12) 0.0244(4) Uani 1 1 d . . . C2 C 0.87477(15) 0.9491(5) 0.48915(14) 0.0264(5) Uani 1 1 d . . . H2 H 0.9288 1.0666 0.5143 0.032 Uiso 1 1 calc R . . N3 N 0.88394(12) 0.7628(4) 0.43268(11) 0.0238(4) Uani 1 1 d . . . C4 C 0.80419(14) 0.6073(4) 0.39736(13) 0.0183(4) Uani 1 1 d . . . C5 C 0.71940(14) 0.6366(4) 0.41881(13) 0.0177(4) Uani 1 1 d . . . C6 C 0.72199(14) 0.8340(4) 0.48116(13) 0.0193(4) Uani 1 1 d . . . N7 N 0.65528(11) 0.4435(3) 0.36851(11) 0.0181(4) Uani 1 1 d . . . C8 C 0.70254(14) 0.3151(4) 0.32055(13) 0.0203(4) Uani 1 1 d . . . H8 H 0.6735 0.1736 0.2793 0.024 Uiso 1 1 calc R . . N9 N 0.79159(12) 0.4024(3) 0.33575(11) 0.0208(4) Uani 1 1 d . . . C10 C 0.55135(14) 0.4114(4) 0.35381(14) 0.0193(4) Uani 1 1 d . . . H10A H 0.5432 0.4122 0.4130 0.023 Uiso 1 1 calc R . . H10B H 0.5286 0.2349 0.3249 0.023 Uiso 1 1 calc R . . C11 C 0.48899(14) 0.6314(4) 0.29503(13) 0.0184(4) Uani 1 1 d . . . C12 C 0.51068(14) 0.7448(4) 0.22432(13) 0.0216(4) Uani 1 1 d . . . H12 H 0.5668 0.6873 0.2132 0.026 Uiso 1 1 calc R . . C13 C 0.45039(16) 0.9417(4) 0.17002(14) 0.0262(5) Uani 1 1 d . . . H13 H 0.4657 1.0191 0.1221 0.031 Uiso 1 1 calc R . . C14 C 0.36767(16) 1.0259(4) 0.18554(15) 0.0262(5) Uani 1 1 d . . . H14 H 0.3264 1.1602 0.1483 0.031 Uiso 1 1 calc R . . C15 C 0.34572(15) 0.9122(4) 0.25590(15) 0.0246(5) Uani 1 1 d . . . H15 H 0.2892 0.9682 0.2666 0.029 Uiso 1 1 calc R . . C16 C 0.40637(14) 0.7171(4) 0.31043(13) 0.0214(4) Uani 1 1 d . . . H16 H 0.3913 0.6413 0.3587 0.026 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 0.0291(3) 0.0278(4) 0.0286(3) -0.00367(19) 0.0160(3) 0.0050(2) N1 0.0250(9) 0.0193(9) 0.0245(9) -0.0013(7) 0.0036(7) -0.0001(7) C2 0.0230(10) 0.0224(11) 0.0288(11) -0.0013(8) 0.0035(9) -0.0036(8) N3 0.0185(8) 0.0227(9) 0.0295(9) 0.0030(7) 0.0078(7) 0.0002(7) C4 0.0174(9) 0.0163(9) 0.0226(10) 0.0037(7) 0.0087(8) 0.0026(7) C5 0.0176(9) 0.0147(9) 0.0205(9) 0.0043(7) 0.0065(8) 0.0024(7) C6 0.0197(9) 0.0178(9) 0.0199(9) 0.0020(7) 0.0066(8) 0.0043(7) N7 0.0175(8) 0.0158(8) 0.0222(8) -0.0011(6) 0.0084(7) 0.0017(6) C8 0.0228(10) 0.0166(9) 0.0241(10) -0.0014(8) 0.0118(8) 0.0020(8) N9 0.0215(9) 0.0183(9) 0.0250(9) 0.0015(6) 0.0113(7) 0.0032(6) C10 0.0163(9) 0.0172(9) 0.0272(10) -0.0002(7) 0.0113(8) -0.0018(7) C11 0.0183(9) 0.0144(9) 0.0221(10) -0.0033(7) 0.0068(8) -0.0031(7) C12 0.0215(10) 0.0211(10) 0.0248(10) -0.0033(8) 0.0117(8) -0.0039(8) C13 0.0310(11) 0.0232(11) 0.0218(10) 0.0002(8) 0.0067(9) -0.0050(9) C14 0.0239(10) 0.0198(10) 0.0284(11) 0.0011(8) 0.0019(8) 0.0010(8) C15 0.0174(9) 0.0232(10) 0.0317(11) -0.0028(8) 0.0074(8) -0.0003(8) C16 0.0179(9) 0.0207(10) 0.0271(10) -0.0004(8) 0.0102(8) -0.0027(8) _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 C6 1.739(2) . ? N1 C6 1.316(3) . ? N1 C2 1.353(3) . ? C2 N3 1.330(3) . ? C2 H2 0.9500 . ? N3 C4 1.346(3) . ? C4 N9 1.378(3) . ? C4 C5 1.416(3) . ? C5 N7 1.379(2) . ? C5 C6 1.385(3) . ? N7 C8 1.363(3) . ? N7 C10 1.470(2) . ? C8 N9 1.317(3) . ? C8 H8 0.9500 . ? C10 C11 1.513(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.392(3) . ? C11 C12 1.394(3) . ? C12 C13 1.390(3) . ? C12 H12 0.9500 . ? C13 C14 1.392(3) . ? C13 H13 0.9500 . ? C14 C15 1.391(3) . ? C14 H14 0.9500 . ? C15 C16 1.388(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 C6 N1 C2 117.28(18) . . ? N3 C2 N1 128.2(2) . . ? N3 C2 H2 115.9 . . ? N1 C2 H2 115.9 . . ? C2 N3 C4 113.22(17) . . ? N3 C4 N9 126.35(18) . . ? N3 C4 C5 123.52(18) . . ? N9 C4 C5 110.13(17) . . ? N7 C5 C6 137.95(19) . . ? N7 C5 C4 105.46(16) . . ? C6 C5 C4 116.59(18) . . ? N1 C6 C5 121.13(19) . . ? N1 C6 Cl1 117.13(16) . . ? C5 C6 Cl1 121.74(16) . . ? C8 N7 C5 105.60(16) . . ? C8 N7 C10 125.00(17) . . ? C5 N7 C10 128.41(16) . . ? N9 C8 N7 114.80(18) . . ? N9 C8 H8 122.6 . . ? N7 C8 H8 122.6 . . ? C8 N9 C4 103.99(16) . . ? N7 C10 C11 112.48(15) . . ? N7 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? N7 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C16 C11 C12 119.27(18) . . ? C16 C11 C10 119.06(18) . . ? C12 C11 C10 121.65(17) . . ? C13 C12 C11 120.21(18) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.27(19) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.6(2) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C16 C15 C14 120.06(19) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 120.61(19) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.381 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.082 # Attachment '1c1.cif' data_rm5a _database_code_depnum_ccdc_archive 'CCDC 742760' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 7-benzyl-6-iodopurine _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 I N4' _chemical_formula_sum 'C12 H9 I N4' _chemical_formula_weight 336.13 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 15.2864(12) _cell_length_b 4.9202(3) _cell_length_c 16.7267(14) _cell_angle_alpha 90.00 _cell_angle_beta 114.466(10) _cell_angle_gamma 90.00 _cell_volume 1145.09(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3455 _cell_measurement_theta_min 2.9045 _cell_measurement_theta_max 28.4245 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.950 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 2.778 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7268 _exptl_absorpt_correction_T_max 0.7614 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.6 (release 21-05-2007 CrysAlis171 .NET) (compiled May 21 2007,16:32:00) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 8.3611 _diffrn_measurement_device_type 'KUMA KM4 + CCD' _diffrn_measurement_method 'rotation method, \w--scan' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5484 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2001 _reflns_number_gt 1815 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0350P)^2^+0.0500P] 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 2001 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0245 _refine_ls_R_factor_gt 0.0213 _refine_ls_wR_factor_ref 0.0547 _refine_ls_wR_factor_gt 0.0532 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.002 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I 0.627240(12) 0.88385(4) 0.526755(11) 0.01692(9) Uani 1 1 d . . . N1 N 0.80683(17) 0.9914(5) 0.50855(16) 0.0170(5) Uani 1 1 d . . . C2 C 0.8789(2) 0.9495(7) 0.48282(19) 0.0185(6) Uani 1 1 d . . . H2 H 0.9323 1.0690 0.5072 0.022 Uiso 1 1 calc R . . N3 N 0.88450(17) 0.7627(5) 0.42785(16) 0.0165(5) Uani 1 1 d . . . C4 C 0.8047(2) 0.6086(5) 0.39212(19) 0.0132(6) Uani 1 1 d . . . C5 C 0.72325(19) 0.6378(5) 0.41130(18) 0.0123(6) Uani 1 1 d . . . C6 C 0.73033(19) 0.8310(6) 0.47471(18) 0.0131(6) Uani 1 1 d . . . N7 N 0.65793(16) 0.4470(5) 0.36071(15) 0.0125(5) Uani 1 1 d . . . C8 C 0.7019(2) 0.3175(6) 0.31455(19) 0.0151(6) Uani 1 1 d . . . H8 H 0.6714 0.1770 0.2734 0.018 Uiso 1 1 calc R . . N9 N 0.78975(17) 0.4034(4) 0.33171(16) 0.0143(5) Uani 1 1 d . . . C10 C 0.55577(19) 0.4161(5) 0.34264(19) 0.0139(6) Uani 1 1 d . . . H10A H 0.5489 0.4185 0.3989 0.017 Uiso 1 1 calc R . . H10B H 0.5329 0.2373 0.3146 0.017 Uiso 1 1 calc R . . C11 C 0.49329(19) 0.6371(5) 0.28354(18) 0.0121(6) Uani 1 1 d . . . C12 C 0.51336(19) 0.7546(6) 0.21660(18) 0.0152(6) Uani 1 1 d . . . H12 H 0.5686 0.6995 0.2083 0.018 Uiso 1 1 calc R . . C13 C 0.4522(2) 0.9524(6) 0.16229(19) 0.0189(6) Uani 1 1 d . . . H13 H 0.4664 1.0322 0.1173 0.023 Uiso 1 1 calc R . . C14 C 0.3714(2) 1.0336(6) 0.17314(19) 0.0194(6) Uani 1 1 d . . . H14 H 0.3302 1.1688 0.1359 0.023 Uiso 1 1 calc R . . C15 C 0.3506(2) 0.9164(6) 0.2390(2) 0.0188(6) Uani 1 1 d . . . H15 H 0.2946 0.9698 0.2463 0.023 Uiso 1 1 calc R . . C16 C 0.4116(2) 0.7218(6) 0.29410(19) 0.0153(6) Uani 1 1 d . . . H16 H 0.3975 0.6451 0.3396 0.018 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 I 0.01751(12) 0.02115(13) 0.01466(12) -0.00089(7) 0.00922(9) 0.00348(7) N1 0.0159(12) 0.0171(12) 0.0153(13) -0.0011(10) 0.0038(10) 0.0013(10) C2 0.0146(15) 0.0190(15) 0.0187(16) -0.0007(12) 0.0037(13) -0.0013(11) N3 0.0151(12) 0.0150(13) 0.0198(13) 0.0013(10) 0.0077(10) 0.0003(10) C4 0.0166(14) 0.0121(14) 0.0110(13) 0.0034(11) 0.0058(11) 0.0028(11) C5 0.0142(14) 0.0104(14) 0.0117(13) 0.0030(11) 0.0049(11) 0.0032(10) C6 0.0149(14) 0.0138(13) 0.0114(13) 0.0049(11) 0.0063(11) 0.0055(11) N7 0.0130(12) 0.0123(12) 0.0126(12) 0.0006(9) 0.0056(10) 0.0008(9) C8 0.0200(15) 0.0123(14) 0.0143(14) 0.0004(12) 0.0084(12) 0.0025(12) N9 0.0176(13) 0.0132(12) 0.0145(12) 0.0008(9) 0.0089(10) 0.0022(9) C10 0.0118(14) 0.0140(14) 0.0170(15) 0.0002(11) 0.0070(12) -0.0016(10) C11 0.0137(14) 0.0102(14) 0.0108(13) -0.0020(10) 0.0035(11) -0.0037(10) C12 0.0158(15) 0.0160(15) 0.0140(15) -0.0036(12) 0.0063(12) -0.0036(11) C13 0.0256(16) 0.0179(15) 0.0113(14) 0.0012(12) 0.0057(13) -0.0046(12) C14 0.0191(15) 0.0161(15) 0.0149(15) 0.0012(12) -0.0009(12) -0.0012(12) C15 0.0157(15) 0.0198(16) 0.0199(16) -0.0038(12) 0.0064(12) 0.0013(11) C16 0.0150(14) 0.0161(15) 0.0150(14) -0.0023(12) 0.0063(12) -0.0052(11) _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 I C6 2.108(3) . ? N1 C6 1.327(4) . ? N1 C2 1.354(4) . ? C2 N3 1.328(4) . ? C2 H2 0.9500 . ? N3 C4 1.348(4) . ? C4 N9 1.379(4) . ? C4 C5 1.415(4) . ? C5 N7 1.376(3) . ? C5 C6 1.395(4) . ? N7 C8 1.372(4) . ? N7 C10 1.471(3) . ? C8 N9 1.322(4) . ? C8 H8 0.9500 . ? C10 C11 1.513(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.396(4) . ? C11 C12 1.402(4) . ? C12 C13 1.394(4) . ? C12 H12 0.9500 . ? C13 C14 1.381(4) . ? C13 H13 0.9500 . ? C14 C15 1.393(4) . ? C14 H14 0.9500 . ? C15 C16 1.387(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 C6 N1 C2 117.6(2) . . ? N3 C2 N1 128.3(3) . . ? N3 C2 H2 115.9 . . ? N1 C2 H2 115.9 . . ? C2 N3 C4 113.0(2) . . ? N3 C4 N9 125.5(3) . . ? N3 C4 C5 124.2(2) . . ? N9 C4 C5 110.3(2) . . ? N7 C5 C6 137.8(3) . . ? N7 C5 C4 105.9(2) . . ? C6 C5 C4 116.3(2) . . ? N1 C6 C5 120.4(2) . . ? N1 C6 I 115.33(19) . . ? C5 C6 I 124.2(2) . . ? C8 N7 C5 105.3(2) . . ? C8 N7 C10 124.2(2) . . ? C5 N7 C10 129.4(2) . . ? N9 C8 N7 114.8(3) . . ? N9 C8 H8 122.6 . . ? N7 C8 H8 122.6 . . ? C8 N9 C4 103.8(2) . . ? N7 C10 C11 112.9(2) . . ? N7 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? N7 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C16 C11 C12 118.8(3) . . ? C16 C11 C10 119.2(2) . . ? C12 C11 C10 122.0(2) . . ? C13 C12 C11 119.9(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 119.6(3) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 120.9(3) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.642 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.092