# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2011 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_cambridge 1326 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jaromir Marek' _publ_contact_author_email marek@chemi.muni.cz loop_ _publ_author_name S.Standara K.Malinakova M.Straka Z.Zacharova M.Hocek J.Marek ; R.Marek ; data_rm-1f _database_code_depnum_ccdc_archive 'CCDC 816403' #TrackingRef '- RM_1f_CCDC_816403.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-benzyl-6-ethynyl-7H-purine ; _chemical_name_common 7-benzyl-6-ethynyl-7H-purine _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 N4' _chemical_formula_weight 234.26 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7837(11) _cell_length_b 8.7711(12) _cell_length_c 10.7042(15) _cell_angle_alpha 75.951(12) _cell_angle_beta 71.904(13) _cell_angle_gamma 77.940(13) _cell_volume 581.10(15) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1787 _cell_measurement_theta_min 2.061 _cell_measurement_theta_max 26.485 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.085 _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 'Mo K\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 4291 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2038 _reflns_number_gt 1616 _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^)+(0.0500P)^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_extinction_coef ? _refine_ls_number_reflns 2038 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0957 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 N1 N 0.3920(2) 0.34308(14) 0.27042(12) 0.0270(3) Uani 1 1 d . . . C2 C 0.4035(2) 0.49912(18) 0.24570(15) 0.0291(4) Uani 1 1 d . . . H2 H 0.4608 0.5449 0.1546 0.035 Uiso 1 1 calc R . . N3 N 0.3455(2) 0.59868(14) 0.33148(12) 0.0271(3) Uani 1 1 d . . . C4 C 0.2739(2) 0.52643(17) 0.45915(14) 0.0223(3) Uani 1 1 d . . . C5 C 0.2599(2) 0.36329(17) 0.49802(14) 0.0214(3) Uani 1 1 d . . . C6 C 0.3164(2) 0.27164(17) 0.39876(14) 0.0231(3) Uani 1 1 d . . . N7 N 0.1819(2) 0.33552(13) 0.63564(11) 0.0232(3) Uani 1 1 d . . . C8 C 0.1530(2) 0.47995(17) 0.67052(15) 0.0255(4) Uani 1 1 d . . . H8 H 0.0998 0.4943 0.7607 0.031 Uiso 1 1 calc R . . N9 N 0.2045(2) 0.59796(14) 0.56935(12) 0.0255(3) Uani 1 1 d . . . C10 C 0.2940(2) 0.10618(17) 0.42547(14) 0.0257(4) Uani 1 1 d . . . C11 C 0.2690(3) -0.0289(2) 0.45073(16) 0.0326(4) Uani 1 1 d . . . C12 C 0.1373(3) 0.18225(17) 0.72572(14) 0.0295(4) Uani 1 1 d . . . H12A H 0.2536 0.0976 0.6976 0.035 Uiso 1 1 calc R . . H12B H 0.0076 0.1552 0.7179 0.035 Uiso 1 1 calc R . . C13 C 0.1113(3) 0.18790(16) 0.86942(14) 0.0250(4) Uani 1 1 d . . . C14 C -0.0866(3) 0.20692(17) 0.95796(15) 0.0306(4) Uani 1 1 d . . . H14 H -0.2068 0.2162 0.9276 0.037 Uiso 1 1 calc R . . C15 C -0.1113(3) 0.21267(18) 1.09079(16) 0.0351(4) Uani 1 1 d . . . H15 H -0.2476 0.2259 1.1506 0.042 Uiso 1 1 calc R . . C16 C 0.0639(3) 0.19899(18) 1.13535(15) 0.0352(4) Uani 1 1 d . . . H16 H 0.0478 0.2031 1.2259 0.042 Uiso 1 1 calc R . . C17 C 0.2626(3) 0.17927(18) 1.04791(15) 0.0344(4) Uani 1 1 d . . . H17 H 0.3826 0.1695 1.0787 0.041 Uiso 1 1 calc R . . C18 C 0.2868(3) 0.17374(17) 0.91545(15) 0.0297(4) Uani 1 1 d . . . H18 H 0.4233 0.1603 0.8559 0.036 Uiso 1 1 calc R . . H11 H 0.246(3) -0.141(2) 0.4777(18) 0.059(6) 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 N1 0.0265(7) 0.0272(7) 0.0265(7) -0.0051(5) -0.0059(6) -0.0044(6) C2 0.0286(9) 0.0293(9) 0.0266(8) -0.0014(7) -0.0058(7) -0.0054(7) N3 0.0273(7) 0.0245(7) 0.0286(7) -0.0026(5) -0.0080(6) -0.0038(6) C4 0.0185(8) 0.0217(8) 0.0272(8) -0.0029(6) -0.0089(6) -0.0019(6) C5 0.0191(8) 0.0209(8) 0.0246(8) -0.0029(6) -0.0080(6) -0.0021(6) C6 0.0192(8) 0.0237(8) 0.0268(8) -0.0052(6) -0.0081(7) -0.0008(6) N7 0.0266(7) 0.0194(6) 0.0240(7) -0.0031(5) -0.0077(6) -0.0043(5) C8 0.0273(9) 0.0227(8) 0.0283(8) -0.0071(6) -0.0095(7) -0.0021(7) N9 0.0275(7) 0.0212(7) 0.0281(7) -0.0049(5) -0.0090(6) -0.0019(6) C10 0.0255(9) 0.0253(9) 0.0285(8) -0.0088(6) -0.0087(7) -0.0020(7) C11 0.0334(10) 0.0272(10) 0.0402(10) -0.0092(7) -0.0123(8) -0.0042(8) C12 0.0420(10) 0.0191(8) 0.0279(8) -0.0002(6) -0.0108(7) -0.0086(7) C13 0.0331(9) 0.0150(7) 0.0260(8) -0.0010(6) -0.0080(7) -0.0049(7) C14 0.0306(10) 0.0224(8) 0.0358(9) -0.0004(7) -0.0110(8) -0.0002(7) C15 0.0364(10) 0.0255(9) 0.0328(9) -0.0049(7) 0.0025(8) -0.0008(8) C16 0.0527(12) 0.0268(9) 0.0252(9) -0.0077(7) -0.0086(8) -0.0038(8) C17 0.0431(11) 0.0299(9) 0.0352(9) -0.0050(7) -0.0178(8) -0.0069(8) C18 0.0300(9) 0.0258(8) 0.0319(9) -0.0046(7) -0.0058(7) -0.0060(7) _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 N1 C2 1.3437(19) . ? N1 C6 1.3497(18) . ? C2 N3 1.3349(19) . ? C2 H2 0.9500 . ? N3 C4 1.3419(18) . ? C4 N9 1.3775(18) . ? C4 C5 1.405(2) . ? C5 N7 1.3801(18) . ? C5 C6 1.3982(19) . ? C6 C10 1.440(2) . ? N7 C8 1.3648(18) . ? N7 C12 1.4793(18) . ? C8 N9 1.3183(19) . ? C8 H8 0.9500 . ? C10 C11 1.186(2) . ? C11 H11 0.98(2) . ? C12 C13 1.505(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.386(2) . ? C13 C18 1.395(2) . ? C14 C15 1.391(2) . ? C14 H14 0.9500 . ? C15 C16 1.385(2) . ? C15 H15 0.9500 . ? C16 C17 1.386(2) . ? C16 H16 0.9500 . ? C17 C18 1.388(2) . ? C17 H17 0.9500 . ? C18 H18 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 C2 N1 C6 117.80(12) . . ? N3 C2 N1 128.92(14) . . ? N3 C2 H2 115.5 . . ? N1 C2 H2 115.5 . . ? C2 N3 C4 112.96(13) . . ? N3 C4 N9 126.15(13) . . ? N3 C4 C5 123.40(13) . . ? N9 C4 C5 110.44(13) . . ? N7 C5 C6 135.55(14) . . ? N7 C5 C4 105.76(12) . . ? C6 C5 C4 118.65(13) . . ? N1 C6 C5 118.15(13) . . ? N1 C6 C10 118.16(13) . . ? C5 C6 C10 123.67(13) . . ? C8 N7 C5 105.24(12) . . ? C8 N7 C12 127.46(12) . . ? C5 N7 C12 127.30(11) . . ? N9 C8 N7 114.83(13) . . ? N9 C8 H8 122.6 . . ? N7 C8 H8 122.6 . . ? C8 N9 C4 103.72(12) . . ? C11 C10 C6 177.67(17) . . ? C10 C11 H11 176.4(11) . . ? N7 C12 C13 111.85(11) . . ? N7 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? N7 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C18 119.04(14) . . ? C14 C13 C12 120.64(15) . . ? C18 C13 C12 120.32(14) . . ? C13 C14 C15 120.82(16) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 119.67(15) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.03(15) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C18 120.17(16) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 120.26(15) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.157 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.040 # Attachment '- RM_1g_CCDC_816404.cif' data_rm-1g _database_code_depnum_ccdc_archive 'CCDC 816404' #TrackingRef '- RM_1g_CCDC_816404.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-benzyl-7H-purine-6-carbonitrile ; _chemical_name_common 7-benzyl-7H-purine-6-carbonitrile _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 N5 ' _chemical_formula_weight 235.25 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.9475(7) _cell_length_b 10.0332(12) _cell_length_c 21.929(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1088.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3472 _cell_measurement_theta_min 2.293 _cell_measurement_theta_max 28.2085 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.093 _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 'Mo K\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 6624 _diffrn_reflns_av_R_equivalents 0.0760 _diffrn_reflns_av_sigmaI/netI 0.0610 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1910 _reflns_number_gt 1733 _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^)+(0.0375P)^2^+0.2500P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1910 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.0924 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _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 N1 N 0.8362(4) 0.37094(17) 0.52289(9) 0.0257(5) Uani 1 1 d . . . C2 C 0.7753(5) 0.4475(2) 0.57070(11) 0.0274(5) Uani 1 1 d . . . H2 H 0.8844 0.4351 0.6059 0.033 Uiso 1 1 calc R . . N3 N 0.5815(4) 0.53924(18) 0.57559(9) 0.0260(5) Uani 1 1 d . . . C4 C 0.4365(5) 0.5547(2) 0.52500(11) 0.0229(5) Uani 1 1 d . . . C5 C 0.4834(5) 0.4818(2) 0.47164(10) 0.0213(5) Uani 1 1 d . . . C6 C 0.6877(5) 0.38758(19) 0.47261(10) 0.0218(5) Uani 1 1 d . . . N7 N 0.2976(4) 0.52661(16) 0.42989(9) 0.0226(4) Uani 1 1 d . . . C8 C 0.1555(5) 0.6233(2) 0.46003(10) 0.0242(5) Uani 1 1 d . . . H8 H 0.0149 0.6728 0.4411 0.029 Uiso 1 1 calc R . . N9 N 0.2269(4) 0.64271(16) 0.51665(9) 0.0246(5) Uani 1 1 d . . . C10 C 0.2842(5) 0.4986(2) 0.36512(10) 0.0244(5) Uani 1 1 d . . . H10A H 0.1057 0.5270 0.3494 0.029 Uiso 1 1 calc R . . H10B H 0.3001 0.4012 0.3588 0.029 Uiso 1 1 calc R . . C11 C 0.5030(5) 0.5681(2) 0.32924(10) 0.0236(5) Uani 1 1 d . . . C12 C 0.6035(5) 0.5113(2) 0.27655(11) 0.0278(6) Uani 1 1 d . . . H12 H 0.5398 0.4262 0.2641 0.033 Uiso 1 1 calc R . . C13 C 0.7943(5) 0.5758(3) 0.24173(11) 0.0323(6) Uani 1 1 d . . . H13 H 0.8602 0.5357 0.2054 0.039 Uiso 1 1 calc R . . C14 C 0.8902(5) 0.6996(3) 0.25972(11) 0.0321(6) Uani 1 1 d . . . H14 H 1.0219 0.7447 0.2359 0.038 Uiso 1 1 calc R . . C15 C 0.7934(5) 0.7563(2) 0.31222(11) 0.0312(6) Uani 1 1 d . . . H15 H 0.8604 0.8406 0.3249 0.037 Uiso 1 1 calc R . . C16 C 0.6001(5) 0.6926(2) 0.34678(11) 0.0263(6) Uani 1 1 d . . . H16 H 0.5328 0.7338 0.3827 0.032 Uiso 1 1 calc R . . C17 C 0.7540(5) 0.3061(2) 0.42071(11) 0.0232(5) Uani 1 1 d . . . N18 N 0.8059(4) 0.24532(18) 0.37823(9) 0.0311(5) 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 N1 0.0303(12) 0.0202(9) 0.0265(11) 0.0012(8) 0.0003(9) -0.0013(8) C2 0.0305(14) 0.0245(11) 0.0272(12) -0.0003(10) -0.0001(12) -0.0003(11) N3 0.0297(12) 0.0195(9) 0.0289(11) 0.0003(8) 0.0016(9) -0.0038(9) C4 0.0236(13) 0.0144(11) 0.0307(13) 0.0022(10) 0.0038(11) -0.0049(10) C5 0.0230(13) 0.0129(10) 0.0281(13) 0.0016(9) 0.0043(10) -0.0029(9) C6 0.0249(13) 0.0170(10) 0.0236(12) 0.0005(9) 0.0059(11) -0.0022(10) N7 0.0200(10) 0.0165(8) 0.0311(10) -0.0007(8) 0.0015(9) -0.0015(8) C8 0.0228(13) 0.0164(10) 0.0335(14) 0.0003(10) 0.0040(11) -0.0006(10) N9 0.0255(12) 0.0161(9) 0.0322(12) -0.0025(8) 0.0037(9) -0.0004(9) C10 0.0250(13) 0.0185(11) 0.0298(12) -0.0006(9) -0.0038(11) 0.0004(10) C11 0.0232(13) 0.0217(12) 0.0257(13) 0.0004(10) -0.0048(10) 0.0021(10) C12 0.0288(14) 0.0246(12) 0.0301(14) -0.0030(10) -0.0051(11) 0.0047(11) C13 0.0362(15) 0.0374(13) 0.0233(13) -0.0003(10) 0.0032(11) 0.0081(13) C14 0.0327(15) 0.0369(14) 0.0266(13) 0.0112(12) 0.0025(12) 0.0004(12) C15 0.0373(16) 0.0244(12) 0.0321(14) 0.0037(10) -0.0007(13) -0.0052(12) C16 0.0321(15) 0.0204(11) 0.0264(13) -0.0020(10) -0.0011(11) 0.0015(11) C17 0.0243(14) 0.0183(10) 0.0270(13) 0.0041(10) 0.0021(11) 0.0006(10) N18 0.0382(13) 0.0253(10) 0.0299(12) 0.0003(9) 0.0059(10) 0.0020(10) _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 N1 C2 1.334(3) . ? N1 C6 1.335(3) . ? C2 N3 1.333(3) . ? C2 H2 0.9500 . ? N3 C4 1.330(3) . ? C4 N9 1.374(3) . ? C4 C5 1.400(3) . ? C5 N7 1.373(3) . ? C5 C6 1.384(3) . ? C6 C17 1.439(3) . ? N7 C8 1.369(3) . ? N7 C10 1.449(3) . ? C8 N9 1.305(3) . ? C8 H8 0.9500 . ? C10 C11 1.509(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.381(3) . ? C11 C16 1.393(3) . ? C12 C13 1.376(3) . ? C12 H12 0.9500 . ? C13 C14 1.387(4) . ? C13 H13 0.9500 . ? C14 C15 1.371(3) . ? C14 H14 0.9500 . ? C15 C16 1.377(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N18 1.143(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 C2 N1 C6 116.9(2) . . ? N3 C2 N1 128.5(2) . . ? N3 C2 H2 115.7 . . ? N1 C2 H2 115.7 . . ? C4 N3 C2 113.67(19) . . ? N3 C4 N9 126.4(2) . . ? N3 C4 C5 123.1(2) . . ? N9 C4 C5 110.5(2) . . ? N7 C5 C6 136.3(2) . . ? N7 C5 C4 105.96(19) . . ? C6 C5 C4 117.7(2) . . ? N1 C6 C5 119.99(19) . . ? N1 C6 C17 117.2(2) . . ? C5 C6 C17 122.8(2) . . ? C8 N7 C5 104.73(19) . . ? C8 N7 C10 125.97(19) . . ? C5 N7 C10 128.34(19) . . ? N9 C8 N7 115.2(2) . . ? N9 C8 H8 122.4 . . ? N7 C8 H8 122.4 . . ? C8 N9 C4 103.63(18) . . ? N7 C10 C11 112.87(19) . . ? 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 . . ? C12 C11 C16 118.5(2) . . ? C12 C11 C10 120.3(2) . . ? C16 C11 C10 121.2(2) . . ? C13 C12 C11 121.1(2) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 119.9(2) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 119.4(2) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 120.8(2) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C11 120.2(2) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? N18 C17 C6 177.6(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.171 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.041 # Attachment '- RM_2b_CCDC_816405.cif' data_rm-2b _database_code_depnum_ccdc_archive 'CCDC 816405' #TrackingRef '- RM_2b_CCDC_816405.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-benzyl-N-methyl-9H-purin-6-amine ; _chemical_name_common 9-benzyl-N-methyl-9H-purin-6-amine _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 N5' _chemical_formula_weight 239.28 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M ' C 2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.133(2) _cell_length_b 8.8277(12) _cell_length_c 13.0345(16) _cell_angle_alpha 90.00 _cell_angle_beta 96.616(10) _cell_angle_gamma 90.00 _cell_volume 2415.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2069 _cell_measurement_theta_min 1.962 _cell_measurement_theta_max 21.9335 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.085 _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 'Mo K\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 11355 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 26.80 _reflns_number_total 2561 _reflns_number_gt 1603 _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^)+(0.0640P)^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 2561 _refine_ls_number_parameters 255 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.952 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.28155(6) 0.62921(14) 0.37772(9) 0.0420(3) Uani 1 1 d . A . C2 C 0.29574(8) 0.58046(19) 0.47494(11) 0.0459(4) Uani 1 1 d . . . H2 H 0.2670 0.6117 0.5218 0.055 Uiso 1 1 calc R . . N3 N 0.34414(6) 0.49468(14) 0.51582(8) 0.0409(3) Uani 1 1 d . A . C4 C 0.38248(6) 0.45915(16) 0.44317(11) 0.0356(4) Uani 1 1 d . . . C5 C 0.37397(6) 0.49889(15) 0.33984(10) 0.0323(3) Uani 1 1 d . A . C6 C 0.31967(6) 0.58626(15) 0.30643(10) 0.0325(3) Uani 1 1 d . . . N6 N 0.30475(5) 0.62600(14) 0.20785(9) 0.0404(3) Uani 1 1 d . A . H6 H 0.3292 0.5937 0.1622 0.048 Uiso 1 1 calc R . . N7 N 0.4265(9) 0.444(2) 0.2966(17) 0.0316(18) Uani 0.475(10) 1 d PU A 1 C8 C 0.4625(7) 0.3836(16) 0.3775(8) 0.034(2) Uani 0.475(10) 1 d P A 1 H8 H 0.5030 0.3407 0.3704 0.040 Uiso 0.475(10) 1 calc PR A 1 N9 N 0.4388(9) 0.3862(17) 0.4711(10) 0.036(2) Uani 0.475(10) 1 d P A 1 C11 C 0.4627(4) 0.3208(10) 0.5701(5) 0.0327(13) Uani 0.475(10) 1 d P A 1 H11A H 0.4526 0.3905 0.6254 0.039 Uiso 0.475(10) 1 calc PR A 1 H11B H 0.5097 0.3136 0.5741 0.039 Uiso 0.475(10) 1 calc PR A 1 C12 C 0.4370(6) 0.1676(14) 0.5909(7) 0.0311(17) Uani 0.475(10) 1 d P A 1 C13 C 0.4070(3) 0.0775(8) 0.5107(5) 0.0425(14) Uani 0.475(10) 1 d P A 1 H13 H 0.4029 0.1143 0.4417 0.051 Uiso 0.475(10) 1 calc PR A 1 C14 C 0.3834(4) -0.0656(11) 0.5312(8) 0.0487(18) Uani 0.475(10) 1 d P A 1 H14 H 0.3634 -0.1260 0.4765 0.058 Uiso 0.475(10) 1 calc PR A 1 C15 C 0.3892(9) -0.120(3) 0.6324(13) 0.058(4) Uani 0.475(10) 1 d P A 1 H15 H 0.3730 -0.2164 0.6476 0.070 Uiso 0.475(10) 1 calc PR A 1 C16 C 0.4187(5) -0.0310(6) 0.7090(4) 0.065(2) Uani 0.475(10) 1 d P A 1 H16 H 0.4247 -0.0691 0.7776 0.078 Uiso 0.475(10) 1 calc PR A 1 C17 C 0.4404(4) 0.1153(6) 0.6892(4) 0.0503(15) Uani 0.475(10) 1 d P A 1 H17 H 0.4575 0.1779 0.7449 0.060 Uiso 0.475(10) 1 calc PR A 1 N7A N 0.4201(9) 0.443(3) 0.2796(16) 0.050(4) Uani 0.525(10) 1 d PU A 2 C8A C 0.4570(6) 0.3631(15) 0.3466(9) 0.042(2) Uani 0.525(10) 1 d P A 2 H8A H 0.4929 0.3072 0.3301 0.050 Uiso 0.525(10) 1 calc PR A 2 N9A N 0.4376(8) 0.3697(13) 0.4440(9) 0.035(2) Uani 0.525(10) 1 d P A 2 C11A C 0.4674(4) 0.2927(9) 0.5362(6) 0.0444(14) Uani 0.525(10) 1 d P A 2 H11C H 0.4676 0.3613 0.5963 0.053 Uiso 0.525(10) 1 calc PR A 2 H11D H 0.5123 0.2691 0.5271 0.053 Uiso 0.525(10) 1 calc PR A 2 C12A C 0.4328(5) 0.1457(11) 0.5581(7) 0.0348(17) Uani 0.525(10) 1 d P A 2 C13A C 0.4256(3) 0.0313(7) 0.4854(5) 0.0459(12) Uani 0.525(10) 1 d P A 2 H13A H 0.4405 0.0445 0.4200 0.055 Uiso 0.525(10) 1 calc PR A 2 C14A C 0.3960(4) -0.1040(9) 0.5089(8) 0.0490(16) Uani 0.525(10) 1 d P A 2 H14A H 0.3891 -0.1811 0.4580 0.059 Uiso 0.525(10) 1 calc PR A 2 C15A C 0.3771(8) -0.126(2) 0.6035(12) 0.050(3) Uani 0.525(10) 1 d P A 2 H15A H 0.3589 -0.2206 0.6191 0.060 Uiso 0.525(10) 1 calc PR A 2 C16A C 0.3837(3) -0.0139(6) 0.6777(5) 0.0553(13) Uani 0.525(10) 1 d P A 2 H16A H 0.3689 -0.0292 0.7430 0.066 Uiso 0.525(10) 1 calc PR A 2 C17A C 0.4125(3) 0.1221(6) 0.6553(6) 0.0466(12) Uani 0.525(10) 1 d P A 2 H17A H 0.4184 0.1993 0.7063 0.056 Uiso 0.525(10) 1 calc PR A 2 C10 C 0.25027(8) 0.7196(2) 0.17195(13) 0.0648(6) Uani 1 1 d . . . H10A H 0.2115 0.6736 0.1926 0.097 Uiso 1 1 calc R A . H10B H 0.2466 0.7277 0.0965 0.097 Uiso 1 1 calc R . . H10C H 0.2559 0.8209 0.2025 0.097 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 N1 0.0423(8) 0.0506(8) 0.0360(7) 0.0102(6) 0.0173(6) 0.0186(6) C2 0.0548(10) 0.0475(9) 0.0388(8) 0.0075(7) 0.0197(7) 0.0192(8) N3 0.0473(8) 0.0394(7) 0.0373(7) 0.0060(5) 0.0100(6) 0.0102(6) C4 0.0296(8) 0.0316(8) 0.0463(8) 0.0070(6) 0.0072(6) 0.0039(6) C5 0.0279(8) 0.0322(8) 0.0391(8) 0.0024(6) 0.0136(6) 0.0030(6) C6 0.0295(8) 0.0364(8) 0.0333(7) 0.0033(6) 0.0107(6) 0.0034(6) N6 0.0335(7) 0.0543(8) 0.0354(7) 0.0084(6) 0.0129(5) 0.0085(6) N7 0.024(4) 0.040(4) 0.035(3) 0.002(2) 0.019(4) 0.009(3) C8 0.028(3) 0.037(4) 0.036(6) 0.002(3) 0.007(3) 0.011(3) N9 0.030(2) 0.051(4) 0.029(5) 0.003(3) 0.007(3) 0.007(2) C11 0.031(2) 0.043(3) 0.023(3) 0.006(2) 0.002(2) 0.0093(19) C12 0.024(3) 0.045(3) 0.024(4) -0.001(3) 0.000(3) 0.010(2) C13 0.040(3) 0.055(4) 0.032(3) 0.011(2) 0.000(2) 0.001(3) C14 0.039(4) 0.047(5) 0.059(4) -0.002(3) -0.001(3) 0.008(3) C15 0.073(10) 0.050(4) 0.057(8) 0.010(5) 0.031(6) 0.009(6) C16 0.092(6) 0.060(3) 0.046(3) 0.014(2) 0.020(3) 0.011(3) C17 0.065(5) 0.050(2) 0.037(3) 0.007(2) 0.010(2) 0.008(3) N7A 0.038(5) 0.046(4) 0.067(9) 0.013(5) 0.015(4) 0.008(3) C8A 0.039(4) 0.042(4) 0.050(6) -0.001(4) 0.024(4) 0.009(3) N9A 0.033(2) 0.034(3) 0.038(6) 0.015(3) 0.007(4) 0.010(2) C11A 0.045(2) 0.044(3) 0.045(4) 0.010(3) 0.007(3) 0.007(2) C12A 0.029(2) 0.037(4) 0.036(5) 0.011(3) -0.005(4) 0.005(3) C13A 0.038(3) 0.047(3) 0.054(3) 0.002(2) 0.0111(18) 0.0062(19) C14A 0.037(3) 0.037(3) 0.074(4) 0.000(2) 0.008(3) 0.008(2) C15A 0.043(3) 0.037(3) 0.069(9) 0.013(5) 0.009(4) 0.001(2) C16A 0.045(3) 0.057(3) 0.066(3) 0.013(2) 0.019(2) 0.000(2) C17A 0.039(3) 0.044(2) 0.058(3) 0.001(2) 0.012(2) 0.007(2) C10 0.0469(10) 0.0955(15) 0.0530(10) 0.0270(10) 0.0102(8) 0.0222(10) _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 N1 C2 1.3392(17) . ? N1 C6 1.3523(17) . ? C2 N3 1.3334(18) . ? C2 H2 0.9500 . ? N3 C4 1.3520(18) . ? C4 N9 1.365(18) . ? C4 C5 1.3833(19) . ? C4 N9A 1.406(15) . ? C5 N7 1.391(14) . ? C5 C6 1.4094(18) . ? C5 N7A 1.410(15) . ? C6 N6 1.3342(17) . ? N6 C10 1.4503(19) . ? N6 H6 0.8800 . ? N7 C8 1.34(3) . ? C8 N9 1.371(16) . ? C8 H8 0.9500 . ? N9 C11 1.450(16) . ? C11 C12 1.494(16) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C17 1.356(12) . ? C12 C13 1.405(8) . ? C13 C14 1.396(12) . ? C13 H13 0.9500 . ? C14 C15 1.39(2) . ? C14 H14 0.9500 . ? C15 C16 1.361(18) . ? C15 H15 0.9500 . ? C16 C17 1.405(7) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? N7A C8A 1.31(3) . ? C8A N9A 1.379(14) . ? C8A H8A 0.9500 . ? N9A C11A 1.459(14) . ? C11A C12A 1.533(14) . ? C11A H11C 0.9900 . ? C11A H11D 0.9900 . ? C12A C13A 1.381(8) . ? C12A C17A 1.399(11) . ? C13A C14A 1.399(11) . ? C13A H13A 0.9500 . ? C14A C15A 1.35(2) . ? C14A H14A 0.9500 . ? C15A C16A 1.38(2) . ? C15A H15A 0.9500 . ? C16A C17A 1.391(7) . ? C16A H16A 0.9500 . ? C17A H17A 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? 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 C2 N1 C6 118.29(12) . . ? N3 C2 N1 129.68(14) . . ? N3 C2 H2 115.2 . . ? N1 C2 H2 115.2 . . ? C2 N3 C4 110.23(12) . . ? N3 C4 N9 119.8(6) . . ? N3 C4 C5 127.01(13) . . ? N9 C4 C5 113.0(6) . . ? N3 C4 N9A 133.4(5) . . ? C5 C4 N9A 99.5(5) . . ? N7 C5 C4 106.6(10) . . ? N7 C5 C6 136.6(10) . . ? C4 C5 C6 116.71(13) . . ? C4 C5 N7A 115.6(9) . . ? C6 C5 N7A 127.6(9) . . ? N6 C6 N1 119.64(12) . . ? N6 C6 C5 122.36(13) . . ? N1 C6 C5 117.99(12) . . ? C6 N6 C10 123.46(12) . . ? C6 N6 H6 118.3 . . ? C10 N6 H6 118.3 . . ? C8 N7 C5 103.1(14) . . ? N7 C8 N9 117.6(14) . . ? N7 C8 H8 121.2 . . ? N9 C8 H8 121.2 . . ? C4 N9 C8 99.6(11) . . ? C4 N9 C11 129.0(12) . . ? C8 N9 C11 131.2(15) . . ? N9 C11 C12 115.2(9) . . ? N9 C11 H11A 108.5 . . ? C12 C11 H11A 108.5 . . ? N9 C11 H11B 108.5 . . ? C12 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C17 C12 C13 118.7(10) . . ? C17 C12 C11 119.9(6) . . ? C13 C12 C11 121.3(8) . . ? C12 C13 C14 120.7(8) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 119.7(11) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 118.7(16) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C15 C16 C17 121.7(10) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C12 C17 C16 120.2(6) . . ? C12 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C8A N7A C5 102.4(14) . . ? N7A C8A N9A 112.0(13) . . ? N7A C8A H8A 124.0 . . ? N9A C8A H8A 124.0 . . ? C8A N9A C4 110.5(10) . . ? C8A N9A C11A 126.3(12) . . ? C4 N9A C11A 123.2(10) . . ? N9A C11A C12A 112.2(8) . . ? N9A C11A H11C 109.2 . . ? C12A C11A H11C 109.2 . . ? N9A C11A H11D 109.2 . . ? C12A C11A H11D 109.2 . . ? H11C C11A H11D 107.9 . . ? C13A C12A C17A 119.4(8) . . ? C13A C12A C11A 120.5(8) . . ? C17A C12A C11A 119.8(5) . . ? C12A C13A C14A 119.4(7) . . ? C12A C13A H13A 120.3 . . ? C14A C13A H13A 120.3 . . ? C15A C14A C13A 120.6(9) . . ? C15A C14A H14A 119.7 . . ? C13A C14A H14A 119.7 . . ? C14A C15A C16A 121.2(13) . . ? C14A C15A H15A 119.4 . . ? C16A C15A H15A 119.4 . . ? C17A C16A C15A 118.9(9) . . ? C17A C16A H16A 120.5 . . ? C15A C16A H16A 120.5 . . ? C16A C17A C12A 120.4(5) . . ? C16A C17A H17A 119.8 . . ? C12A C17A H17A 119.8 . . ? N6 C10 H10A 109.5 . . ? N6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.80 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.202 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.040