# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_yb16 _database_code_depnum_ccdc_archive 'CCDC 905035' #TrackingRef 'yb16.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H9 N5 O2' _chemical_formula_weight 183.18 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' O O 0.0106 0.0060 '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/a ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 10.619(3) _cell_length_b 5.430(2) _cell_length_c 14.639(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.69(2) _cell_angle_gamma 90.00 _cell_volume 799.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 3. _cell_measurement_theta_max 26.3 _exptl_crystal_description platelike _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.119 _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 'RU200 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '140 images, \D\F 3\%' _diffrn_detector_area_resol_mean 6.66 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12338 _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 26.37 _reflns_number_total 1620 _reflns_number_gt 1468 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement MAR _computing_data_reduction MARHKL _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The data were not corrected for absorption but the collection mode take at least partially the absorption phenomena into account (see the total number of images and collected reflexions vs the number of independent reflexions). The H atoms were localized by Fourier difference and refined with a common isotropic temperature parameter (U~eq~ = 0.024 \%A^2^). 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^)+(0.0584P)^2^+0.3815P] 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 refxyz _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.086(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1620 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 1.206 _refine_ls_restrained_S_all 1.206 _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 0.53797(12) 0.0292(2) 0.62500(9) 0.0171(3) Uani 1 1 d . . . N2 N 0.54463(14) -0.2132(2) 0.64568(10) 0.0233(3) Uani 1 1 d . . . N3 N 0.42395(14) -0.2953(3) 0.61415(10) 0.0259(4) Uani 1 1 d . . . N4 N 0.33718(13) -0.1116(3) 0.57239(10) 0.0248(4) Uani 1 1 d . . . C5 C 0.41094(15) 0.0870(3) 0.58068(11) 0.0199(4) Uani 1 1 d . . . C6 C 0.65629(15) 0.1852(3) 0.65500(11) 0.0197(4) Uani 1 1 d . . . C7 C 0.68396(15) 0.2823(3) 0.75729(11) 0.0199(4) Uani 1 1 d . . . N8 N 0.71362(12) 0.0898(2) 0.82956(9) 0.0187(3) Uani 1 1 d . . . C9 C 0.61756(15) -0.0209(3) 0.85701(11) 0.0202(4) Uani 1 1 d . . . O10 O 0.66898(11) -0.2172(2) 0.91433(8) 0.0251(3) Uani 1 1 d . . . C11 C 0.81235(17) -0.2208(3) 0.93296(12) 0.0259(4) Uani 1 1 d . . . C12 C 0.83374(16) -0.0596(3) 0.85417(13) 0.0247(4) Uani 1 1 d . . . O13 O 0.50183(11) 0.0393(2) 0.83737(9) 0.0277(3) Uani 1 1 d . . . H5 H 0.3815(18) 0.248(4) 0.5583(14) 0.0242(16) Uiso 1 1 d . . . H6A H 0.7275(19) 0.082(4) 0.6478(14) 0.0242(16) Uiso 1 1 d . . . H6B H 0.6411(18) 0.325(4) 0.6133(14) 0.0242(16) Uiso 1 1 d . . . H7A H 0.6074(19) 0.373(4) 0.7629(13) 0.0242(16) Uiso 1 1 d . . . H7B H 0.760(2) 0.393(4) 0.7712(14) 0.0242(16) Uiso 1 1 d . . . H11A H 0.8380(19) -0.393(4) 0.9281(13) 0.0242(16) Uiso 1 1 d . . . H11B H 0.8551(18) -0.149(4) 0.9971(14) 0.0242(16) Uiso 1 1 d . . . H12A H 0.9118(19) 0.042(4) 0.8792(14) 0.0242(16) Uiso 1 1 d . . . H12B H 0.8350(18) -0.157(4) 0.7966(14) 0.0242(16) 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 0.0194(6) 0.0147(6) 0.0174(6) 0.0008(5) 0.0063(5) 0.0005(5) N2 0.0259(7) 0.0163(7) 0.0267(7) 0.0018(5) 0.0071(5) 0.0007(5) N3 0.0286(7) 0.0191(7) 0.0281(7) -0.0016(5) 0.0062(6) -0.0027(5) N4 0.0229(7) 0.0229(7) 0.0262(7) -0.0026(6) 0.0048(5) -0.0023(5) C5 0.0200(7) 0.0192(8) 0.0201(7) -0.0004(6) 0.0056(6) 0.0013(6) C6 0.0172(7) 0.0190(8) 0.0233(8) 0.0038(6) 0.0072(6) -0.0006(6) C7 0.0183(8) 0.0167(7) 0.0229(8) 0.0011(6) 0.0040(6) -0.0015(6) N8 0.0159(6) 0.0187(7) 0.0207(7) 0.0016(5) 0.0046(5) 0.0004(5) C9 0.0228(8) 0.0189(7) 0.0192(7) -0.0036(6) 0.0072(6) -0.0016(6) O10 0.0282(6) 0.0236(6) 0.0250(6) 0.0044(5) 0.0106(5) 0.0006(5) C11 0.0263(9) 0.0263(9) 0.0238(8) 0.0036(7) 0.0062(6) 0.0052(7) C12 0.0180(8) 0.0260(9) 0.0287(9) 0.0061(7) 0.0056(6) 0.0037(6) O13 0.0204(6) 0.0303(7) 0.0345(7) -0.0008(5) 0.0117(5) 0.0001(5) _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 C5 1.333(2) . ? N1 N2 1.3471(19) . ? N1 C6 1.4613(19) . ? N2 N3 1.294(2) . ? N3 N4 1.363(2) . ? N4 C5 1.315(2) . ? C5 H5 0.95(2) . ? C6 C7 1.525(2) . ? C6 H6A 0.97(2) . ? C6 H6B 0.95(2) . ? C7 N8 1.449(2) . ? C7 H7A 0.977(19) . ? C7 H7B 0.98(2) . ? N8 C9 1.351(2) . ? N8 C12 1.456(2) . ? C9 O13 1.2138(19) . ? C9 O10 1.3584(19) . ? O10 C11 1.458(2) . ? C11 C12 1.522(2) . ? C11 H11A 0.98(2) . ? C11 H11B 0.98(2) . ? C12 H12A 0.97(2) . ? C12 H12B 1.00(2) . ? 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 C5 N1 N2 108.14(13) . . ? C5 N1 C6 130.39(13) . . ? N2 N1 C6 121.37(13) . . ? N3 N2 N1 106.37(13) . . ? N2 N3 N4 110.95(13) . . ? C5 N4 N3 105.17(13) . . ? N4 C5 N1 109.36(14) . . ? N4 C5 H5 126.9(11) . . ? N1 C5 H5 123.7(11) . . ? N1 C6 C7 111.86(12) . . ? N1 C6 H6A 104.9(11) . . ? C7 C6 H6A 113.2(11) . . ? N1 C6 H6B 108.4(11) . . ? C7 C6 H6B 107.1(12) . . ? H6A C6 H6B 111.4(16) . . ? N8 C7 C6 113.32(13) . . ? N8 C7 H7A 107.1(11) . . ? C6 C7 H7A 110.7(11) . . ? N8 C7 H7B 108.7(11) . . ? C6 C7 H7B 107.7(11) . . ? H7A C7 H7B 109.2(16) . . ? C9 N8 C7 122.01(13) . . ? C9 N8 C12 111.32(13) . . ? C7 N8 C12 123.44(12) . . ? O13 C9 N8 127.83(15) . . ? O13 C9 O10 122.26(14) . . ? N8 C9 O10 109.90(13) . . ? C9 O10 C11 108.36(12) . . ? O10 C11 C12 104.53(12) . . ? O10 C11 H11A 107.2(11) . . ? C12 C11 H11A 112.3(11) . . ? O10 C11 H11B 108.0(11) . . ? C12 C11 H11B 111.2(12) . . ? H11A C11 H11B 113.0(16) . . ? N8 C12 C11 100.16(13) . . ? N8 C12 H12A 110.6(12) . . ? C11 C12 H12A 111.1(12) . . ? N8 C12 H12B 109.5(11) . . ? C11 C12 H12B 112.5(12) . . ? H12A C12 H12B 112.4(16) . . ? 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 C5 N1 N2 N3 -0.04(16) . . . . ? C6 N1 N2 N3 176.81(13) . . . . ? N1 N2 N3 N4 0.29(17) . . . . ? N2 N3 N4 C5 -0.43(18) . . . . ? N3 N4 C5 N1 0.40(17) . . . . ? N2 N1 C5 N4 -0.24(17) . . . . ? C6 N1 C5 N4 -176.70(14) . . . . ? C5 N1 C6 C7 90.13(18) . . . . ? N2 N1 C6 C7 -85.93(17) . . . . ? N1 C6 C7 N8 63.40(16) . . . . ? C6 C7 N8 C9 -90.15(17) . . . . ? C6 C7 N8 C12 67.76(18) . . . . ? C7 N8 C9 O13 -10.2(2) . . . . ? C12 N8 C9 O13 -170.53(16) . . . . ? C7 N8 C9 O10 171.02(13) . . . . ? C12 N8 C9 O10 10.70(18) . . . . ? O13 C9 O10 C11 -173.17(15) . . . . ? N8 C9 O10 C11 5.68(16) . . . . ? C9 O10 C11 C12 -18.63(17) . . . . ? C9 N8 C12 C11 -21.09(17) . . . . ? C7 N8 C12 C11 178.93(14) . . . . ? O10 C11 C12 N8 22.97(16) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.263 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.072 data_yb17 _database_code_depnum_ccdc_archive 'CCDC 905036' #TrackingRef 'yb17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H11 N9 O' _chemical_formula_weight 237.25 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' O O 0.0106 0.0060 '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/a ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 12.849(3) _cell_length_b 5.378(2) _cell_length_c 16.169(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.50(2) _cell_angle_gamma 90.00 _cell_volume 1090.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 3.9 _cell_measurement_theta_max 23.4 _exptl_crystal_description platelike _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.109 _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 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'RU200 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '200 images, \D\F 3\%' _diffrn_detector_area_resol_mean 6.66 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4521 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 23.24 _reflns_number_total 1525 _reflns_number_gt 1315 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement MAR _computing_data_reduction MARHKL _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The data were not corrected for absorption but the collection mode take at least partially the absorption phenomena into account (see the total number of images and collected reflexions vs the number of independent reflexions). The H atoms were localized by Fourier difference and refined with a common isotropic temperature parameter (U~eq~ = 0.059 \%A^2^). 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^)+(0.0487P)^2^+0.3161P] 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 refxyz _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.036(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1525 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _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 0.74951(13) 0.0531(3) 0.40126(10) 0.0468(5) Uani 1 1 d . . . N2 N 0.69884(16) -0.1297(4) 0.43333(12) 0.0635(6) Uani 1 1 d . . . N3 N 0.60067(17) -0.0649(5) 0.42139(14) 0.0737(6) Uani 1 1 d . . . N4 N 0.58511(16) 0.1584(4) 0.38137(14) 0.0745(6) Uani 1 1 d . . . C5 C 0.67851(19) 0.2237(5) 0.37041(16) 0.0598(6) Uani 1 1 d . . . C6 C 0.86271(17) 0.0355(5) 0.40180(15) 0.0558(6) Uani 1 1 d . . . C7 C 0.88291(18) -0.1197(5) 0.32874(14) 0.0521(6) Uani 1 1 d . . . N8 N 0.82528(12) -0.0271(3) 0.24709(10) 0.0445(5) Uani 1 1 d . . . C9 C 0.87037(18) 0.1799(4) 0.20883(14) 0.0475(5) Uani 1 1 d . . . C10 C 0.96090(17) 0.1027(4) 0.16748(14) 0.0492(6) Uani 1 1 d . . . N11 N 0.92286(13) -0.0556(3) 0.09360(11) 0.0461(5) Uani 1 1 d . . . N12 N 0.92678(18) -0.3034(3) 0.09914(14) 0.0681(6) Uani 1 1 d . . . N13 N 0.88578(18) -0.3861(4) 0.02365(16) 0.0741(7) Uani 1 1 d . . . N14 N 0.85525(16) -0.1971(4) -0.03123(13) 0.0658(6) Uani 1 1 d . . . C15 C 0.87922(18) 0.0039(4) 0.01410(15) 0.0542(6) Uani 1 1 d . . . C16 C 0.73379(18) -0.1344(5) 0.20845(15) 0.0573(6) Uani 1 1 d . . . O17 O 0.69324(14) -0.3139(4) 0.23530(12) 0.0798(6) Uani 1 1 d . . . H5 H 0.6949(18) 0.361(5) 0.3466(14) 0.0592(19) Uiso 1 1 d . . . H6A H 0.8882(19) 0.202(5) 0.3964(15) 0.0592(19) Uiso 1 1 d . . . H6B H 0.8974(19) -0.030(4) 0.4519(16) 0.0592(19) Uiso 1 1 d . . . H7A H 0.8640(18) -0.284(5) 0.3358(14) 0.0592(19) Uiso 1 1 d . . . H7B H 0.961(2) -0.125(4) 0.3298(13) 0.0592(19) Uiso 1 1 d . . . H9A H 0.8975(18) 0.304(4) 0.2516(15) 0.0592(19) Uiso 1 1 d . . . H9B H 0.8091(18) 0.260(4) 0.1675(14) 0.0592(19) Uiso 1 1 d . . . H10A H 1.0162(19) 0.003(4) 0.2077(15) 0.0592(19) Uiso 1 1 d . . . H10B H 0.9934(18) 0.248(4) 0.1467(14) 0.0592(19) Uiso 1 1 d . . . H14 H 0.8723(18) 0.166(5) -0.0028(15) 0.0592(19) Uiso 1 1 d . . . H16 H 0.7007(18) -0.051(4) 0.1529(16) 0.0592(19) 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 0.0477(10) 0.0527(11) 0.0384(9) 0.0007(8) 0.0060(7) -0.0055(8) N2 0.0617(13) 0.0689(13) 0.0591(12) 0.0112(10) 0.0117(9) -0.0128(10) N3 0.0573(13) 0.0922(17) 0.0729(14) 0.0035(12) 0.0174(10) -0.0149(11) N4 0.0549(13) 0.0885(17) 0.0804(15) 0.0007(12) 0.0157(10) 0.0060(11) C5 0.0618(15) 0.0533(14) 0.0640(15) 0.0050(11) 0.0127(11) 0.0032(12) C6 0.0463(12) 0.0735(16) 0.0434(12) 0.0036(11) 0.0006(9) -0.0067(11) C7 0.0473(13) 0.0517(13) 0.0546(13) 0.0088(10) 0.0052(10) 0.0061(10) N8 0.0429(9) 0.0463(10) 0.0437(10) -0.0002(7) 0.0076(7) 0.0007(8) C9 0.0534(13) 0.0399(12) 0.0490(12) -0.0020(9) 0.0106(10) 0.0019(9) C10 0.0489(12) 0.0464(12) 0.0522(13) -0.0003(10) 0.0108(10) -0.0037(10) N11 0.0481(10) 0.0373(10) 0.0565(11) -0.0012(8) 0.0194(8) -0.0006(7) N12 0.0894(15) 0.0389(11) 0.0796(15) 0.0008(10) 0.0262(12) 0.0009(10) N13 0.0868(15) 0.0495(12) 0.0915(17) -0.0167(12) 0.0314(13) -0.0086(11) N14 0.0672(13) 0.0615(13) 0.0688(13) -0.0151(11) 0.0151(10) -0.0051(10) C15 0.0596(14) 0.0447(13) 0.0591(15) -0.0018(11) 0.0144(11) -0.0017(11) C16 0.0550(14) 0.0632(15) 0.0515(13) -0.0049(11) 0.0070(11) -0.0071(12) O17 0.0736(12) 0.0816(13) 0.0804(12) 0.0009(10) 0.0085(9) -0.0303(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 C5 1.314(3) . ? N1 N2 1.343(2) . ? N1 C6 1.456(3) . ? N2 N3 1.282(3) . ? N3 N4 1.358(3) . ? N4 C5 1.299(3) . ? C5 H5 0.88(2) . ? C6 C7 1.514(3) . ? C6 H6A 0.96(2) . ? C6 H6B 0.91(2) . ? C7 N8 1.455(3) . ? C7 H7A 0.93(2) . ? C7 H7B 1.00(2) . ? N8 C16 1.337(3) . ? N8 C9 1.453(3) . ? C9 C10 1.519(3) . ? C9 H9A 0.97(2) . ? C9 H9B 1.01(2) . ? C10 N11 1.462(3) . ? C10 H10A 1.01(2) . ? C10 H10B 0.98(2) . ? N11 C15 1.326(3) . ? N11 N12 1.336(2) . ? N12 N13 1.299(3) . ? N13 N14 1.350(3) . ? N14 C15 1.305(3) . ? C15 H14 0.91(3) . ? C16 O17 1.221(3) . ? C16 H16 1.01(2) . ? 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 C5 N1 N2 107.63(19) . . ? C5 N1 C6 131.2(2) . . ? N2 N1 C6 121.15(19) . . ? N3 N2 N1 106.62(19) . . ? N2 N3 N4 110.53(19) . . ? C5 N4 N3 105.0(2) . . ? N4 C5 N1 110.2(2) . . ? N4 C5 H5 127.0(15) . . ? N1 C5 H5 122.7(15) . . ? N1 C6 C7 111.77(18) . . ? N1 C6 H6A 107.3(14) . . ? C7 C6 H6A 108.8(14) . . ? N1 C6 H6B 109.2(15) . . ? C7 C6 H6B 110.4(15) . . ? H6A C6 H6B 109(2) . . ? N8 C7 C6 112.30(18) . . ? N8 C7 H7A 110.0(14) . . ? C6 C7 H7A 109.5(15) . . ? N8 C7 H7B 109.7(13) . . ? C6 C7 H7B 110.0(12) . . ? H7A C7 H7B 105.2(19) . . ? C16 N8 C9 121.51(18) . . ? C16 N8 C7 119.98(19) . . ? C9 N8 C7 118.50(17) . . ? N8 C9 C10 113.07(17) . . ? N8 C9 H9A 109.8(13) . . ? C10 C9 H9A 108.1(13) . . ? N8 C9 H9B 106.5(12) . . ? C10 C9 H9B 112.7(13) . . ? H9A C9 H9B 106.5(18) . . ? N11 C10 C9 111.48(17) . . ? N11 C10 H10A 106.3(13) . . ? C9 C10 H10A 111.2(13) . . ? N11 C10 H10B 106.0(13) . . ? C9 C10 H10B 111.0(14) . . ? H10A C10 H10B 110.7(19) . . ? C15 N11 N12 107.90(18) . . ? C15 N11 C10 130.42(18) . . ? N12 N11 C10 121.67(18) . . ? N13 N12 N11 106.07(19) . . ? N12 N13 N14 111.16(18) . . ? C15 N14 N13 104.8(2) . . ? N14 C15 N11 110.1(2) . . ? N14 C15 H14 128.9(15) . . ? N11 C15 H14 120.9(15) . . ? O17 C16 N8 125.1(2) . . ? O17 C16 H16 122.3(13) . . ? N8 C16 H16 112.6(13) . . ? 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 C5 N1 N2 N3 -0.2(2) . . . . ? C6 N1 N2 N3 -177.99(19) . . . . ? N1 N2 N3 N4 0.3(3) . . . . ? N2 N3 N4 C5 -0.3(3) . . . . ? N3 N4 C5 N1 0.1(3) . . . . ? N2 N1 C5 N4 0.1(3) . . . . ? C6 N1 C5 N4 177.5(2) . . . . ? C5 N1 C6 C7 -95.5(3) . . . . ? N2 N1 C6 C7 81.7(2) . . . . ? N1 C6 C7 N8 56.0(3) . . . . ? C6 C7 N8 C16 -99.4(2) . . . . ? C6 C7 N8 C9 81.5(2) . . . . ? C16 N8 C9 C10 -101.1(2) . . . . ? C7 N8 C9 C10 77.9(2) . . . . ? N8 C9 C10 N11 67.0(2) . . . . ? C9 C10 N11 C15 83.5(3) . . . . ? C9 C10 N11 N12 -95.2(2) . . . . ? C15 N11 N12 N13 0.0(2) . . . . ? C10 N11 N12 N13 178.95(17) . . . . ? N11 N12 N13 N14 0.1(3) . . . . ? N12 N13 N14 C15 -0.1(3) . . . . ? N13 N14 C15 N11 0.1(3) . . . . ? N12 N11 C15 N14 0.0(2) . . . . ? C10 N11 C15 N14 -178.91(19) . . . . ? C9 N8 C16 O17 177.3(2) . . . . ? C7 N8 C16 O17 -1.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 23.24 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.182 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.054