# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2007 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _publ_section_title ;Highly fluorescent donor-acceptor purines ; _publ_contact_author_name 'Prof. Ronald Castellano' _publ_contact_author_email CASTELLANO@CHEM.UFL.EDU loop_ _publ_author_name 'Khalil A. Abboud' 'Prabhu Bellarmine' 'Roslyn S. Butler' 'Andrea K. Myers' data_rlm2 _database_code_depnum_ccdc_archive 'CCDC 630370' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 N7' _chemical_formula_weight 293.34 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 8.5576(6) _cell_length_b 9.1964(7) _cell_length_c 10.2811(7) _cell_angle_alpha 79.739(1) _cell_angle_beta 74.878(1) _cell_angle_gamma 65.164(1) _cell_volume 706.68(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 58 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9819 _exptl_absorpt_correction_T_max 0.9894 _exptl_absorpt_process_details 'based on measured indexed crystal faces, Bruker SHELXTL v6.14 (Bruker 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'SMART CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 4656 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3099 _reflns_number_gt 2624 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART v5.624 (Bruker 1998)' _computing_cell_refinement 'Bruker SMART v5.624 & SAINT 6.36a (Bruker 1998)' _computing_data_reduction 'Bruker SHELXTL v6.14 (Bruker 2000)' _computing_structure_solution 'Bruker SHELXTL v6.14' _computing_structure_refinement 'Bruker SHELXTL v6.14' _computing_molecular_graphics 'Bruker SHELXTL v6.14' _computing_publication_material 'Bruker SHELXTL v6.14' _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^)+(0.0624P)^2^+0.1284P] 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 3099 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.24132(13) 0.39985(12) -0.11767(10) 0.0260(2) Uani 1 1 d . . . C2 C 0.33021(15) 0.25565(14) -0.05696(11) 0.0248(2) Uani 1 1 d . . . N3 N 0.39388(13) 0.22551(11) 0.05628(9) 0.0242(2) Uani 1 1 d . . . C4 C 0.36353(14) 0.36389(13) 0.10415(11) 0.0222(2) Uani 1 1 d . . . C5 C 0.27895(15) 0.52058(13) 0.05124(11) 0.0234(2) Uani 1 1 d . . . C6 C 0.21327(14) 0.53543(13) -0.06699(11) 0.0240(2) Uani 1 1 d . . . N7 N 0.27708(13) 0.63084(11) 0.12755(10) 0.0256(2) Uani 1 1 d . . . C8 C 0.35759(15) 0.54148(14) 0.22400(11) 0.0242(2) Uani 1 1 d . . . N9 N 0.41338(12) 0.37798(11) 0.21652(9) 0.0231(2) Uani 1 1 d . . . N10 N 0.12722(14) 0.67593(12) -0.13204(10) 0.0300(2) Uani 1 1 d . . . N11 N 0.35326(16) 0.12704(13) -0.11826(12) 0.0340(3) Uani 1 1 d . . . H11A H 0.427(2) 0.022(2) -0.0954(17) 0.050(5) Uiso 1 1 d . . . H11B H 0.324(2) 0.149(2) -0.1990(17) 0.047(5) Uiso 1 1 d . . . C12 C 0.38330(16) 0.60717(14) 0.32902(12) 0.0282(3) Uani 1 1 d . . . N13 N 0.39907(16) 0.66263(14) 0.41343(12) 0.0382(3) Uani 1 1 d . . . C14 C 0.06424(18) 0.67768(16) -0.25104(13) 0.0359(3) Uani 1 1 d . . . H14A H 0.0065 0.7868 -0.2850 0.054 Uiso 0.50 1 calc PR A 1 H14B H -0.0174 0.6261 -0.2273 0.054 Uiso 0.50 1 calc PR A 1 H14C H 0.1621 0.6213 -0.3194 0.054 Uiso 0.50 1 calc PR A 1 H14D H 0.1074 0.7548 -0.3247 0.054 Uiso 0.50 1 d PR A 2 H14E H -0.0824 0.7429 -0.2370 0.054 Uiso 0.50 1 d PR A 2 H14F H 0.0977 0.5747 -0.2802 0.054 Uiso 0.50 1 d PR A 2 C15 C 0.0770(2) 0.83092(15) -0.08130(14) 0.0395(3) Uani 1 1 d . . . H15A H -0.0483 0.8886 -0.0691 0.059 Uiso 0.50 1 calc PR B 3 H15B H 0.1348 0.8919 -0.1450 0.059 Uiso 0.50 1 calc PR B 3 H15C H 0.1112 0.8144 0.0037 0.059 Uiso 0.50 1 calc PR B 3 H15D H 0.0175 0.9154 -0.1427 0.059 Uiso 0.50 1 calc PR B 4 H15E H 0.1805 0.8427 -0.0737 0.059 Uiso 0.50 1 calc PR B 4 H15F H -0.0002 0.8368 0.0059 0.059 Uiso 0.50 1 calc PR B 4 C16 C 0.34348(14) 0.21110(13) 0.42119(11) 0.0237(2) Uani 1 1 d . . . C17 C 0.31416(16) 0.07446(14) 0.41809(12) 0.0288(3) Uani 1 1 d . . . H17 H 0.3835 0.0039 0.3515 0.035 Uiso 1 1 calc R . . C18 C 0.18214(17) 0.04242(15) 0.51366(14) 0.0330(3) Uani 1 1 d . . . H18 H 0.1640 -0.0498 0.5111 0.040 Uiso 1 1 calc R . . C19 C 0.07740(16) 0.14711(16) 0.61271(13) 0.0325(3) Uani 1 1 d . . . H19 H -0.0125 0.1265 0.6756 0.039 Uiso 1 1 calc R . . C20 C 0.10703(18) 0.28253(17) 0.61772(13) 0.0360(3) Uani 1 1 d . . . H20 H 0.0378 0.3526 0.6847 0.043 Uiso 1 1 calc R . . C21 C 0.23977(17) 0.31403(15) 0.52298(13) 0.0325(3) Uani 1 1 d . . . H21 H 0.2598 0.4047 0.5274 0.039 Uiso 1 1 calc R . . C22 C 0.48585(15) 0.24878(14) 0.31747(11) 0.0243(2) Uani 1 1 d . . . H22A H 0.5515 0.2802 0.3630 0.029 Uiso 1 1 calc R . . H22B H 0.5669 0.1528 0.2722 0.029 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 0.0285(5) 0.0244(5) 0.0239(5) -0.0045(4) -0.0063(4) -0.0077(4) C2 0.0261(6) 0.0239(6) 0.0239(5) -0.0052(4) -0.0041(4) -0.0087(4) N3 0.0283(5) 0.0213(5) 0.0230(5) -0.0039(4) -0.0055(4) -0.0087(4) C4 0.0225(5) 0.0244(5) 0.0197(5) -0.0039(4) -0.0017(4) -0.0100(4) C5 0.0257(5) 0.0218(5) 0.0214(5) -0.0043(4) -0.0016(4) -0.0090(4) C6 0.0241(5) 0.0237(5) 0.0213(5) -0.0026(4) -0.0008(4) -0.0085(4) N7 0.0287(5) 0.0245(5) 0.0239(5) -0.0060(4) -0.0016(4) -0.0116(4) C8 0.0270(5) 0.0236(5) 0.0234(5) -0.0061(4) -0.0017(4) -0.0117(4) N9 0.0261(5) 0.0232(5) 0.0211(5) -0.0047(4) -0.0037(4) -0.0105(4) N10 0.0377(6) 0.0225(5) 0.0266(5) -0.0012(4) -0.0095(4) -0.0075(4) N11 0.0470(7) 0.0239(5) 0.0322(6) -0.0071(4) -0.0183(5) -0.0072(5) C12 0.0308(6) 0.0256(6) 0.0291(6) -0.0059(5) -0.0044(5) -0.0115(5) N13 0.0468(7) 0.0342(6) 0.0384(6) -0.0108(5) -0.0120(5) -0.0157(5) C14 0.0415(7) 0.0317(6) 0.0333(7) 0.0021(5) -0.0165(5) -0.0098(5) C15 0.0504(8) 0.0224(6) 0.0391(7) -0.0029(5) -0.0106(6) -0.0070(6) C16 0.0251(5) 0.0251(5) 0.0217(5) -0.0003(4) -0.0090(4) -0.0088(4) C17 0.0303(6) 0.0242(6) 0.0311(6) -0.0045(5) -0.0078(5) -0.0081(5) C18 0.0352(7) 0.0252(6) 0.0412(7) 0.0022(5) -0.0114(5) -0.0141(5) C19 0.0291(6) 0.0362(7) 0.0313(6) 0.0048(5) -0.0064(5) -0.0147(5) C20 0.0364(7) 0.0401(7) 0.0299(6) -0.0098(5) 0.0011(5) -0.0155(6) C21 0.0375(7) 0.0315(6) 0.0318(6) -0.0091(5) -0.0012(5) -0.0175(5) C22 0.0249(5) 0.0242(5) 0.0231(5) -0.0036(4) -0.0062(4) -0.0077(4) _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 C6 1.3411(15) . ? N1 C2 1.3536(15) . ? C2 N3 1.3484(15) . ? C2 N11 1.3563(15) . ? N3 C4 1.3446(14) . ? C4 N9 1.3749(14) . ? C4 C5 1.3952(16) . ? C5 N7 1.3810(14) . ? C5 C6 1.4301(16) . ? C6 N10 1.3450(15) . ? N7 C8 1.3129(16) . ? C8 N9 1.3834(14) . ? C8 C12 1.4308(15) . ? N9 C22 1.4666(14) . ? N10 C14 1.4552(16) . ? N10 C15 1.4565(15) . ? N11 H11A 0.932(19) . ? N11 H11B 0.894(17) . ? C12 N13 1.1437(16) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C14 H14D 1.0461 . ? C14 H14E 1.1225 . ? C14 H14F 0.9476 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C15 H15D 0.9600 . ? C15 H15E 0.9600 . ? C15 H15F 0.9600 . ? C16 C17 1.3878(16) . ? C16 C21 1.3934(16) . ? C16 C22 1.5122(15) . ? C17 C18 1.3878(18) . ? C17 H17 0.9300 . ? C18 C19 1.3839(18) . ? C18 H18 0.9300 . ? C19 C20 1.3831(19) . ? C19 H19 0.9300 . ? C20 C21 1.3862(18) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? 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 119.68(10) . . ? N3 C2 N1 128.27(10) . . ? N3 C2 N11 117.20(10) . . ? N1 C2 N11 114.51(10) . . ? C4 N3 C2 110.37(10) . . ? N3 C4 N9 125.99(10) . . ? N3 C4 C5 128.08(10) . . ? N9 C4 C5 105.93(9) . . ? N7 C5 C4 110.83(10) . . ? N7 C5 C6 133.41(11) . . ? C4 C5 C6 115.76(10) . . ? N1 C6 N10 117.64(10) . . ? N1 C6 C5 117.78(10) . . ? N10 C6 C5 124.57(10) . . ? C8 N7 C5 103.84(9) . . ? N7 C8 N9 114.17(10) . . ? N7 C8 C12 123.04(10) . . ? N9 C8 C12 122.77(11) . . ? C4 N9 C8 105.22(9) . . ? C4 N9 C22 126.95(9) . . ? C8 N9 C22 127.25(9) . . ? C6 N10 C14 120.18(10) . . ? C6 N10 C15 122.78(10) . . ? C14 N10 C15 116.76(10) . . ? C2 N11 H11A 122.9(11) . . ? C2 N11 H11B 115.9(11) . . ? H11A N11 H11B 118.2(15) . . ? N13 C12 C8 178.09(14) . . ? N10 C14 H14A 109.5 . . ? N10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N10 C14 H14D 105.7 . . ? H14A C14 H14D 46.9 . . ? H14B C14 H14D 143.2 . . ? H14C C14 H14D 67.1 . . ? N10 C14 H14E 112.1 . . ? H14A C14 H14E 56.0 . . ? H14B C14 H14E 55.5 . . ? H14C C14 H14E 138.4 . . ? H14D C14 H14E 101.3 . . ? N10 C14 H14F 114.4 . . ? H14A C14 H14F 135.8 . . ? H14B C14 H14F 60.0 . . ? H14C C14 H14F 50.9 . . ? H14D C14 H14F 113.6 . . ? H14E C14 H14F 109.0 . . ? N10 C15 H15A 109.5 . . ? N10 C15 H15B 109.5 . . ? N10 C15 H15C 109.5 . . ? N10 C15 H15D 109.5 . . ? H15A C15 H15D 54.7 . . ? H15B C15 H15D 57.8 . . ? H15C C15 H15D 141.0 . . ? N10 C15 H15E 109.5 . . ? H15A C15 H15E 141.0 . . ? H15B C15 H15E 54.7 . . ? H15C C15 H15E 57.8 . . ? H15D C15 H15E 109.5 . . ? N10 C15 H15F 109.5 . . ? H15A C15 H15F 57.8 . . ? H15B C15 H15F 141.0 . . ? H15C C15 H15F 54.7 . . ? H15D C15 H15F 109.5 . . ? H15E C15 H15F 109.5 . . ? C17 C16 C21 118.82(11) . . ? C17 C16 C22 121.30(10) . . ? C21 C16 C22 119.88(10) . . ? C18 C17 C16 120.47(11) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C19 C18 C17 120.29(11) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 119.68(12) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C21 120.09(12) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C16 120.63(11) . . ? C20 C21 H21 119.7 . . ? C16 C21 H21 119.7 . . ? N9 C22 C16 112.08(9) . . ? N9 C22 H22A 109.2 . . ? C16 C22 H22A 109.2 . . ? N9 C22 H22B 109.2 . . ? C16 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.229 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.061 ###END data_rlm3 _database_code_depnum_ccdc_archive 'CCDC 630371' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 N7' _chemical_formula_weight 293.34 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 P21/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 10.0863(8) _cell_length_b 8.6914(7) _cell_length_c 16.9812(14) _cell_angle_alpha 90.00 _cell_angle_beta 98.137(2) _cell_angle_gamma 90.00 _cell_volume 1473.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 81 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9803 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_process_details 'based on measured indexed crystal faces, Bruker SHELXTL v6.14 (Bruker 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'SMART CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 9095 _diffrn_reflns_av_R_equivalents 0.0615 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3304 _reflns_number_gt 2770 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART v5.624 (Bruker 1998)' _computing_cell_refinement 'Bruker SMART v5.624 & SAINT 6.36a (Bruker 1998)' _computing_data_reduction 'Bruker SHELXTL v6.14 (Bruker 2000)' _computing_structure_solution 'Bruker SHELXTL v6.14' _computing_structure_refinement 'Bruker SHELXTL v6.14' _computing_molecular_graphics 'Bruker SHELXTL v6.14' _computing_publication_material 'Bruker SHELXTL v6.14' _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^)+(0.0543P)^2^+0.6005P] 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 3304 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1200 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.70829(12) 0.31616(14) -0.07922(7) 0.0289(3) Uani 1 1 d . . . C2 C 0.70165(14) 0.45737(17) -0.04476(8) 0.0256(3) Uani 1 1 d . . . N3 N 0.78278(12) 0.51284(14) 0.01960(7) 0.0255(3) Uani 1 1 d . . . C4 C 0.87794(13) 0.41162(16) 0.04609(8) 0.0230(3) Uani 1 1 d . . . C5 C 0.89785(14) 0.26601(16) 0.01605(8) 0.0245(3) Uani 1 1 d . . . C6 C 0.80530(15) 0.21968(17) -0.05021(8) 0.0271(3) Uani 1 1 d . . . N7 N 1.00767(12) 0.19454(15) 0.05827(7) 0.0272(3) Uani 1 1 d . . . C8 C 1.05213(14) 0.29723(17) 0.11290(8) 0.0265(3) Uani 1 1 d . . . N9 N 0.97853(11) 0.43124(14) 0.10918(7) 0.0246(3) Uani 1 1 d . . . N10 N 0.81225(16) 0.08092(17) -0.08399(9) 0.0417(4) Uani 1 1 d . . . H10A H 0.880(2) 0.012(3) -0.0657(13) 0.056(6) Uiso 1 1 d . . . H10B H 0.756(2) 0.064(3) -0.1297(14) 0.059(6) Uiso 1 1 d . . . N11 N 0.60321(13) 0.55119(15) -0.07891(8) 0.0325(3) Uani 1 1 d . . . C12 C 1.16786(15) 0.27241(19) 0.17138(9) 0.0310(3) Uani 1 1 d . . . N13 N 1.25865(14) 0.2492(2) 0.21811(9) 0.0450(4) Uani 1 1 d . . . C14 C 0.58324(17) 0.70309(19) -0.04696(10) 0.0366(4) Uani 1 1 d . . . H14A H 0.6524 0.7229 -0.0015 0.055 Uiso 1 1 calc R . . H14B H 0.4947 0.7081 -0.0297 0.055 Uiso 1 1 calc R . . H14C H 0.5891 0.7807 -0.0882 0.055 Uiso 1 1 calc R . . C15 C 0.50768(17) 0.5043(2) -0.14720(10) 0.0398(4) Uani 1 1 d . . . H15A H 0.5300 0.4006 -0.1638 0.060 Uiso 1 1 calc R . . H15B H 0.5117 0.5764 -0.1912 0.060 Uiso 1 1 calc R . . H15C H 0.4171 0.5042 -0.1326 0.060 Uiso 1 1 calc R . . C16 C 0.92782(14) 0.55186(16) 0.23418(8) 0.0248(3) Uani 1 1 d . . . C17 C 0.81578(17) 0.6400(2) 0.24107(10) 0.0365(4) Uani 1 1 d . . . H17 H 0.7825 0.7095 0.1998 0.044 Uiso 1 1 calc R . . C18 C 0.75157(18) 0.6274(2) 0.30818(11) 0.0451(4) Uani 1 1 d . . . H18 H 0.6743 0.6879 0.3122 0.054 Uiso 1 1 calc R . . C19 C 0.79919(19) 0.5281(2) 0.36880(11) 0.0418(4) Uani 1 1 d . . . H19 H 0.7550 0.5196 0.4144 0.050 Uiso 1 1 calc R . . C20 C 0.91225(18) 0.4406(2) 0.36272(10) 0.0376(4) Uani 1 1 d . . . H20 H 0.9463 0.3727 0.4046 0.045 Uiso 1 1 calc R . . C21 C 0.97546(15) 0.45199(18) 0.29581(9) 0.0305(3) Uani 1 1 d . . . H21 H 1.0523 0.3909 0.2919 0.037 Uiso 1 1 calc R . . C22 C 0.99874(15) 0.56644(17) 0.16176(9) 0.0279(3) Uani 1 1 d . . . H22A H 0.9654 0.6592 0.1314 0.033 Uiso 1 1 calc R . . H22B H 1.0958 0.5804 0.1793 0.033 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 0.0307(7) 0.0266(6) 0.0275(6) -0.0020(5) -0.0022(5) 0.0037(5) C2 0.0265(7) 0.0260(7) 0.0240(7) 0.0032(5) 0.0029(5) 0.0017(6) N3 0.0281(6) 0.0235(6) 0.0245(6) 0.0008(5) 0.0020(5) 0.0021(5) C4 0.0229(6) 0.0251(7) 0.0210(6) 0.0015(5) 0.0037(5) -0.0016(5) C5 0.0252(7) 0.0247(7) 0.0235(7) 0.0019(5) 0.0028(5) 0.0023(6) C6 0.0292(7) 0.0258(7) 0.0255(7) -0.0006(6) 0.0009(5) 0.0024(6) N7 0.0272(6) 0.0279(6) 0.0259(6) 0.0008(5) 0.0019(5) 0.0033(5) C8 0.0243(7) 0.0292(7) 0.0256(7) 0.0025(6) 0.0024(5) 0.0015(6) N9 0.0241(6) 0.0260(6) 0.0233(6) -0.0002(5) 0.0015(5) 0.0003(5) N10 0.0467(9) 0.0314(8) 0.0403(8) -0.0110(6) -0.0166(7) 0.0125(7) N11 0.0354(7) 0.0282(7) 0.0316(7) -0.0003(5) -0.0036(5) 0.0080(6) C12 0.0274(7) 0.0364(9) 0.0288(8) -0.0008(6) 0.0025(6) 0.0043(6) N13 0.0330(7) 0.0623(10) 0.0377(8) 0.0016(7) -0.0019(6) 0.0097(7) C14 0.0395(9) 0.0308(8) 0.0385(8) -0.0011(7) 0.0022(7) 0.0115(7) C15 0.0368(9) 0.0388(9) 0.0392(9) 0.0012(7) -0.0103(7) 0.0072(7) C16 0.0247(7) 0.0232(7) 0.0254(7) -0.0039(5) -0.0003(5) -0.0035(5) C17 0.0370(8) 0.0359(9) 0.0350(8) -0.0015(7) -0.0006(7) 0.0095(7) C18 0.0375(9) 0.0499(11) 0.0495(10) -0.0100(9) 0.0114(8) 0.0099(8) C19 0.0473(10) 0.0435(10) 0.0382(9) -0.0100(8) 0.0186(8) -0.0060(8) C20 0.0499(10) 0.0328(8) 0.0302(8) 0.0019(6) 0.0065(7) -0.0023(7) C21 0.0301(7) 0.0297(8) 0.0310(8) -0.0012(6) 0.0020(6) 0.0023(6) C22 0.0315(7) 0.0251(7) 0.0262(7) -0.0027(6) 0.0013(6) -0.0050(6) _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 C6 1.3292(19) . ? N1 C2 1.3654(19) . ? C2 N11 1.3506(19) . ? C2 N3 1.3577(18) . ? N3 C4 1.3323(18) . ? C4 N9 1.3779(17) . ? C4 C5 1.390(2) . ? C5 N7 1.3791(18) . ? C5 C6 1.415(2) . ? C6 N10 1.342(2) . ? N7 C8 1.3192(19) . ? C8 N9 1.3779(19) . ? C8 C12 1.438(2) . ? N9 C22 1.4725(18) . ? N10 H10A 0.93(2) . ? N10 H10B 0.91(2) . ? N11 C14 1.452(2) . ? N11 C15 1.457(2) . ? C12 N13 1.142(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.384(2) . ? C16 C21 1.392(2) . ? C16 C22 1.513(2) . ? C17 C18 1.392(2) . ? C17 H17 0.9500 . ? C18 C19 1.377(3) . ? C18 H18 0.9500 . ? C19 C20 1.387(3) . ? C19 H19 0.9500 . ? C20 C21 1.383(2) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? 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 119.11(13) . . ? N11 C2 N3 117.00(13) . . ? N11 C2 N1 115.87(13) . . ? N3 C2 N1 127.13(13) . . ? C4 N3 C2 111.13(12) . . ? N3 C4 N9 126.64(13) . . ? N3 C4 C5 127.74(13) . . ? N9 C4 C5 105.62(12) . . ? N7 C5 C4 111.51(12) . . ? N7 C5 C6 132.54(13) . . ? C4 C5 C6 115.96(13) . . ? N1 C6 N10 119.28(14) . . ? N1 C6 C5 118.90(13) . . ? N10 C6 C5 121.82(14) . . ? C8 N7 C5 103.23(12) . . ? N7 C8 N9 114.35(12) . . ? N7 C8 C12 123.10(14) . . ? N9 C8 C12 122.55(13) . . ? C8 N9 C4 105.29(12) . . ? C8 N9 C22 128.27(12) . . ? C4 N9 C22 126.43(12) . . ? C6 N10 H10A 121.0(14) . . ? C6 N10 H10B 116.8(14) . . ? H10A N10 H10B 122(2) . . ? C2 N11 C14 121.39(13) . . ? C2 N11 C15 122.41(13) . . ? C14 N11 C15 116.15(13) . . ? N13 C12 C8 178.34(19) . . ? N11 C14 H14A 109.5 . . ? N11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N11 C15 H15A 109.5 . . ? N11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 118.73(14) . . ? C17 C16 C22 120.53(14) . . ? C21 C16 C22 120.72(13) . . ? C16 C17 C18 120.38(16) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 120.50(16) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 119.46(15) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C21 C20 C19 120.10(16) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C16 120.82(15) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? N9 C22 C16 112.66(12) . . ? N9 C22 H22A 109.1 . . ? C16 C22 H22A 109.1 . . ? N9 C22 H22B 109.1 . . ? C16 C22 H22B 109.1 . . ? H22A C22 H22B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.275 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.047 # Formatted by publCIF