# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'J.E. Davies' _publ_contact_author_email jed2@cam.ac.uk loop_ _publ_author_name C.Smith N.Nikbin S.Ley H.Lange I.R.Baxendale # Attachment 'sl0926.cif' data_sl0926 _database_code_depnum_ccdc_archive 'CCDC 791579' #TrackingRef 'sl0926.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H9 N5 O' _chemical_formula_sum 'C10 H9 N5 O' _chemical_formula_weight 215.22 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' 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 27.8326(7) _cell_length_b 6.2301(2) _cell_length_c 11.8916(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.99(3) _cell_angle_gamma 90.00 _cell_volume 2054.20(15) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6875 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 32.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 10352 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 32.00 _reflns_number_total 3544 _reflns_number_gt 2918 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0530P)^2^+1.4080P] 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 3544 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 O1 O 0.21531(3) 0.19323(14) 0.59637(7) 0.03023(19) Uani 1 1 d . . . N1 N 0.10347(3) 0.43184(15) 0.94082(7) 0.02308(18) Uani 1 1 d . . . N2 N 0.10677(4) 0.33486(17) 1.04552(8) 0.0295(2) Uani 1 1 d . . . N3 N 0.07796(4) 0.43723(17) 1.10660(8) 0.0281(2) Uani 1 1 d . . . N4 N -0.00184(4) 0.8746(2) 1.11955(9) 0.0378(3) Uani 1 1 d . . . N5 N 0.05977(4) 0.71391(17) 0.84355(8) 0.0308(2) Uani 1 1 d . . . H5A H 0.0734 0.6878 0.7809 0.037 Uiso 1 1 calc R . . H5B H 0.0385 0.8182 0.8456 0.037 Uiso 1 1 calc R . . C1 C 0.07136(4) 0.59506(16) 0.93572(8) 0.02126(19) Uani 1 1 d . . . C2 C 0.05561(4) 0.59947(17) 1.04393(8) 0.0228(2) Uani 1 1 d . . . C3 C 0.02364(4) 0.74836(19) 1.08746(8) 0.0266(2) Uani 1 1 d . . . C4 C 0.13256(4) 0.36354(17) 0.85358(8) 0.0223(2) Uani 1 1 d . . . C5 C 0.17310(4) 0.4813(2) 0.83253(10) 0.0310(2) Uani 1 1 d . . . H5 H 0.1823 0.6034 0.8773 0.037 Uiso 1 1 calc R . . C6 C 0.20001(4) 0.4192(2) 0.74569(10) 0.0322(3) Uani 1 1 d . . . H6 H 0.2277 0.4996 0.7301 0.039 Uiso 1 1 calc R . . C7 C 0.18660(4) 0.23842(17) 0.68078(8) 0.0231(2) Uani 1 1 d . . . C6' C 0.14659(4) 0.11832(18) 0.70382(9) 0.0261(2) Uani 1 1 d . . . H6' H 0.1379 -0.0066 0.6610 0.031 Uiso 1 1 calc R . . C5' C 0.11934(4) 0.18348(19) 0.79072(9) 0.0265(2) Uani 1 1 d . . . H5' H 0.0916 0.1038 0.8067 0.032 Uiso 1 1 calc R . . C8 C 0.20311(5) 0.0091(2) 0.52848(11) 0.0384(3) Uani 1 1 d . . . H8A H 0.2262 -0.0062 0.4712 0.058 Uiso 1 1 calc R . . H8B H 0.1705 0.0262 0.4913 0.058 Uiso 1 1 calc R . . H8C H 0.2043 -0.1193 0.5763 0.058 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 O1 0.0308(4) 0.0327(4) 0.0293(4) -0.0091(3) 0.0144(3) -0.0046(3) N1 0.0277(4) 0.0242(4) 0.0181(4) 0.0003(3) 0.0063(3) 0.0033(3) N2 0.0366(5) 0.0327(5) 0.0199(4) 0.0042(3) 0.0065(3) 0.0084(4) N3 0.0343(5) 0.0312(5) 0.0195(4) 0.0019(3) 0.0068(3) 0.0060(4) N4 0.0475(6) 0.0406(6) 0.0272(5) 0.0028(4) 0.0145(4) 0.0138(5) N5 0.0448(6) 0.0294(5) 0.0197(4) 0.0039(3) 0.0102(4) 0.0126(4) C1 0.0253(4) 0.0212(4) 0.0178(4) -0.0013(3) 0.0050(3) 0.0002(4) C2 0.0266(5) 0.0252(5) 0.0173(4) -0.0007(3) 0.0056(3) 0.0008(4) C3 0.0318(5) 0.0304(5) 0.0186(4) 0.0012(4) 0.0076(4) 0.0028(4) C4 0.0244(4) 0.0236(5) 0.0196(4) -0.0008(3) 0.0060(3) 0.0030(4) C5 0.0313(5) 0.0310(6) 0.0319(5) -0.0120(4) 0.0089(4) -0.0066(4) C6 0.0285(5) 0.0338(6) 0.0361(6) -0.0113(5) 0.0124(4) -0.0099(4) C7 0.0234(4) 0.0249(5) 0.0217(4) -0.0026(4) 0.0061(3) 0.0007(4) C6' 0.0287(5) 0.0243(5) 0.0263(5) -0.0057(4) 0.0086(4) -0.0040(4) C5' 0.0279(5) 0.0259(5) 0.0272(5) -0.0037(4) 0.0099(4) -0.0042(4) C8 0.0476(7) 0.0364(7) 0.0339(6) -0.0127(5) 0.0191(5) -0.0068(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 O1 C7 1.3658(12) . ? O1 C8 1.4269(15) . ? N1 C1 1.3517(13) . ? N1 N2 1.3797(12) . ? N1 C4 1.4348(13) . ? N2 N3 1.2957(13) . ? N3 C2 1.3722(14) . ? N4 C3 1.1466(15) . ? N5 C1 1.3387(13) . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? C1 C2 1.3953(13) . ? C2 C3 1.4145(15) . ? C4 C5' 1.3801(15) . ? C4 C5 1.3870(16) . ? C5 C6 1.3827(16) . ? C5 H5 0.9500 . ? C6 C7 1.3977(15) . ? C6 H6 0.9500 . ? C7 C6' 1.3884(15) . ? C6' C5' 1.3945(14) . ? C6' H6' 0.9500 . ? C5' H5' 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 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 C7 O1 C8 117.12(9) . . ? C1 N1 N2 111.21(8) . . ? C1 N1 C4 127.09(9) . . ? N2 N1 C4 121.68(9) . . ? N3 N2 N1 107.13(9) . . ? N2 N3 C2 109.36(9) . . ? C1 N5 H5A 120.0 . . ? C1 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? N5 C1 N1 124.34(9) . . ? N5 C1 C2 132.19(10) . . ? N1 C1 C2 103.47(9) . . ? N3 C2 C1 108.81(9) . . ? N3 C2 C3 123.66(9) . . ? C1 C2 C3 127.49(10) . . ? N4 C3 C2 177.31(12) . . ? C5' C4 C5 121.00(9) . . ? C5' C4 N1 119.48(9) . . ? C5 C4 N1 119.51(10) . . ? C6 C5 C4 119.26(10) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C7 120.13(10) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? O1 C7 C6' 124.37(10) . . ? O1 C7 C6 115.26(9) . . ? C6' C7 C6 120.37(10) . . ? C7 C6' C5' 119.12(10) . . ? C7 C6' H6' 120.4 . . ? C5' C6' H6' 120.4 . . ? C4 C5' C6' 120.10(10) . . ? C4 C5' H5' 120.0 . . ? C6' C5' H5' 120.0 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 C1 N1 N2 N3 -1.18(13) . . . . ? C4 N1 N2 N3 177.19(10) . . . . ? N1 N2 N3 C2 0.19(13) . . . . ? N2 N1 C1 N5 -178.03(11) . . . . ? C4 N1 C1 N5 3.71(18) . . . . ? N2 N1 C1 C2 1.61(12) . . . . ? C4 N1 C1 C2 -176.65(10) . . . . ? N2 N3 C2 C1 0.81(13) . . . . ? N2 N3 C2 C3 -176.79(11) . . . . ? N5 C1 C2 N3 178.14(12) . . . . ? N1 C1 C2 N3 -1.46(12) . . . . ? N5 C1 C2 C3 -4.4(2) . . . . ? N1 C1 C2 C3 176.02(11) . . . . ? N3 C2 C3 N4 155(3) . . . . ? C1 C2 C3 N4 -22(3) . . . . ? C1 N1 C4 C5' -102.16(13) . . . . ? N2 N1 C4 C5' 79.74(14) . . . . ? C1 N1 C4 C5 76.83(15) . . . . ? N2 N1 C4 C5 -101.27(13) . . . . ? C5' C4 C5 C6 1.29(19) . . . . ? N1 C4 C5 C6 -177.69(11) . . . . ? C4 C5 C6 C7 -0.6(2) . . . . ? C8 O1 C7 C6' -0.40(17) . . . . ? C8 O1 C7 C6 179.59(11) . . . . ? C5 C6 C7 O1 179.18(12) . . . . ? C5 C6 C7 C6' -0.83(19) . . . . ? O1 C7 C6' C5' -178.47(11) . . . . ? C6 C7 C6' C5' 1.55(18) . . . . ? C5 C4 C5' C6' -0.57(18) . . . . ? N1 C4 C5' C6' 178.41(10) . . . . ? C7 C6' C5' C4 -0.85(17) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 32.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.344 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.046 # Attachment 'sl0975.cif' data_sl0975 _database_code_depnum_ccdc_archive 'CCDC 791580' #TrackingRef 'sl0975.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H7 N5' _chemical_formula_sum 'C11 H7 N5' _chemical_formula_weight 209.22 _chemical_absolute_configuration ; 786 Friedel pairs were averaged for the refinement ; 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 Cc _symmetry_space_group_name_Hall 'C -2yc' 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' _cell_length_a 10.1129(2) _cell_length_b 14.7360(5) _cell_length_c 7.3628(2) _cell_angle_alpha 90.00 _cell_angle_beta 118.152(3) _cell_angle_gamma 90.00 _cell_volume 967.43(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3880 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 5715 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.18 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1106 _reflns_number_gt 996 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0435P)^2^+0.0808P] 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 -2(2) _refine_ls_number_reflns 1106 _refine_ls_number_parameters 146 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0702 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.049 _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 0.32002(16) 0.49144(11) 0.2311(2) 0.0290(4) Uani 1 1 d . . . N2 N 0.2255(2) 0.55775(11) 0.2322(3) 0.0357(4) Uani 1 1 d . . . N3 N 0.1094(2) 0.51515(11) 0.2262(2) 0.0367(4) Uani 1 1 d . . . N4 N -0.0650(2) 0.30787(14) 0.2101(4) 0.0504(5) Uani 1 1 d . . . N5 N 0.33693(17) 0.32865(10) 0.2256(2) 0.0325(4) Uani 1 1 d . . . C1 C 0.2645(2) 0.40702(11) 0.2254(2) 0.0295(4) Uani 1 1 d . . . C2 C 0.1287(2) 0.42360(12) 0.2217(3) 0.0326(4) Uani 1 1 d . . . C3 C 0.0211(2) 0.35994(14) 0.2153(3) 0.0383(5) Uani 1 1 d . . . C4 C 0.4594(2) 0.50578(14) 0.2412(3) 0.0299(4) Uani 1 1 d . . . C5 C 0.5156(2) 0.59219(13) 0.2461(3) 0.0341(5) Uani 1 1 d . . . H5 H 0.4591 0.6447 0.2398 0.041 Uiso 1 1 calc R . . C6 C 0.6569(2) 0.59948(15) 0.2606(3) 0.0396(5) Uani 1 1 d . . . H6 H 0.6977 0.6578 0.2633 0.048 Uiso 1 1 calc R . . C7 C 0.7399(2) 0.52212(15) 0.2712(3) 0.0408(5) Uani 1 1 d . . . H7 H 0.8374 0.5283 0.2836 0.049 Uiso 1 1 calc R . . C8 C 0.6814(2) 0.43682(16) 0.2639(3) 0.0373(5) Uani 1 1 d . . . H8 H 0.7387 0.3847 0.2702 0.045 Uiso 1 1 calc R . . C9 C 0.5382(2) 0.42627(13) 0.2473(2) 0.0304(4) Uani 1 1 d . . . C10 C 0.4697(2) 0.33772(13) 0.2373(3) 0.0326(5) Uani 1 1 d . . . C11 C 0.5513(2) 0.25240(16) 0.2401(3) 0.0438(6) Uani 1 1 d . . . H11A H 0.4871 0.1999 0.2236 0.066 Uiso 1 1 calc R . . H11B H 0.6435 0.2478 0.3717 0.066 Uiso 1 1 calc R . . H11C H 0.5765 0.2538 0.1270 0.066 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 0.0306(9) 0.0271(7) 0.0271(8) -0.0011(6) 0.0117(7) 0.0021(6) N2 0.0366(9) 0.0332(9) 0.0377(8) -0.0006(7) 0.0178(7) 0.0068(8) N3 0.0380(9) 0.0340(8) 0.0387(9) -0.0003(7) 0.0186(7) 0.0043(8) N4 0.0428(11) 0.0424(11) 0.0733(13) 0.0048(9) 0.0334(10) 0.0024(8) N5 0.0350(10) 0.0299(8) 0.0284(8) 0.0002(6) 0.0115(7) 0.0059(7) C1 0.0306(11) 0.0301(9) 0.0251(10) 0.0009(7) 0.0109(8) 0.0002(7) C2 0.0316(11) 0.0339(9) 0.0315(10) 0.0016(8) 0.0142(8) 0.0040(8) C3 0.0356(12) 0.0368(10) 0.0438(11) 0.0032(8) 0.0198(9) 0.0068(8) C4 0.0286(10) 0.0362(10) 0.0227(10) -0.0004(7) 0.0102(8) 0.0008(7) C5 0.0415(12) 0.0310(10) 0.0263(10) -0.0012(7) 0.0130(9) -0.0003(9) C6 0.0406(13) 0.0452(12) 0.0307(11) -0.0001(8) 0.0150(10) -0.0087(9) C7 0.0327(12) 0.0576(15) 0.0305(11) -0.0005(9) 0.0137(9) -0.0041(9) C8 0.0334(11) 0.0497(12) 0.0278(11) -0.0007(8) 0.0136(9) 0.0067(9) C9 0.0307(10) 0.0357(10) 0.0213(10) 0.0003(7) 0.0095(8) 0.0053(7) C10 0.0349(11) 0.0356(11) 0.0231(9) 0.0005(7) 0.0102(8) 0.0072(8) C11 0.0444(14) 0.0352(10) 0.0488(13) -0.0001(9) 0.0193(11) 0.0135(9) _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 C1 1.357(2) . ? N1 N2 1.370(2) . ? N1 C4 1.392(2) . ? N2 N3 1.314(3) . ? N3 C2 1.366(2) . ? N4 C3 1.147(3) . ? N5 C10 1.311(3) . ? N5 C1 1.367(2) . ? C1 C2 1.382(3) . ? C2 C3 1.420(3) . ? C4 C5 1.388(3) . ? C4 C9 1.406(2) . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.396(3) . ? C6 H6 0.9500 . ? C7 C8 1.380(3) . ? C7 H7 0.9500 . ? C8 C9 1.403(3) . ? C8 H8 0.9500 . ? C9 C10 1.463(3) . ? C10 C11 1.498(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 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 C1 N1 N2 111.99(15) . . ? C1 N1 C4 122.31(14) . . ? N2 N1 C4 125.67(16) . . ? N3 N2 N1 105.90(16) . . ? N2 N3 C2 109.71(17) . . ? C10 N5 C1 116.47(17) . . ? N1 C1 N5 124.07(16) . . ? N1 C1 C2 103.38(15) . . ? N5 C1 C2 132.55(17) . . ? N3 C2 C1 109.02(17) . . ? N3 C2 C3 122.50(18) . . ? C1 C2 C3 128.47(17) . . ? N4 C3 C2 179.4(2) . . ? C5 C4 N1 122.20(17) . . ? C5 C4 C9 122.98(18) . . ? N1 C4 C9 114.82(17) . . ? C6 C5 C4 117.92(18) . . ? C6 C5 H5 121.0 . . ? C4 C5 H5 121.0 . . ? C5 C6 C7 120.8(2) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 120.4(2) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 120.7(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C4 117.18(18) . . ? C8 C9 C10 123.23(17) . . ? C4 C9 C10 119.59(17) . . ? N5 C10 C9 122.70(17) . . ? N5 C10 C11 117.09(19) . . ? C9 C10 C11 120.21(17) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 C1 N1 N2 N3 -0.3(2) . . . . ? C4 N1 N2 N3 -178.33(15) . . . . ? N1 N2 N3 C2 0.1(2) . . . . ? N2 N1 C1 N5 -179.20(16) . . . . ? C4 N1 C1 N5 -1.1(2) . . . . ? N2 N1 C1 C2 0.32(19) . . . . ? C4 N1 C1 C2 178.45(15) . . . . ? C10 N5 C1 N1 1.8(2) . . . . ? C10 N5 C1 C2 -177.60(18) . . . . ? N2 N3 C2 C1 0.1(2) . . . . ? N2 N3 C2 C3 179.9(2) . . . . ? N1 C1 C2 N3 -0.24(19) . . . . ? N5 C1 C2 N3 179.22(18) . . . . ? N1 C1 C2 C3 180.0(2) . . . . ? N5 C1 C2 C3 -0.5(4) . . . . ? N3 C2 C3 N4 -179(100) . . . . ? C1 C2 C3 N4 1(23) . . . . ? C1 N1 C4 C5 179.71(14) . . . . ? N2 N1 C4 C5 -2.4(2) . . . . ? C1 N1 C4 C9 -0.7(2) . . . . ? N2 N1 C4 C9 177.17(16) . . . . ? N1 C4 C5 C6 178.65(16) . . . . ? C9 C4 C5 C6 -0.9(2) . . . . ? C4 C5 C6 C7 -0.4(3) . . . . ? C5 C6 C7 C8 1.1(3) . . . . ? C6 C7 C8 C9 -0.5(3) . . . . ? C7 C8 C9 C4 -0.8(3) . . . . ? C7 C8 C9 C10 179.52(16) . . . . ? C5 C4 C9 C8 1.5(2) . . . . ? N1 C4 C9 C8 -178.09(14) . . . . ? C5 C4 C9 C10 -178.78(16) . . . . ? N1 C4 C9 C10 1.6(2) . . . . ? C1 N5 C10 C9 -0.7(2) . . . . ? C1 N5 C10 C11 179.31(17) . . . . ? C8 C9 C10 N5 178.72(15) . . . . ? C4 C9 C10 N5 -1.0(2) . . . . ? C8 C9 C10 C11 -1.3(3) . . . . ? C4 C9 C10 C11 178.98(17) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.154 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.032 # Attachment 'sl1007.cif' data_sl1007 _database_code_depnum_ccdc_archive 'CCDC 791582' #TrackingRef 'sl1007.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 N5' _chemical_formula_sum 'C12 H13 N5' _chemical_formula_weight 227.27 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' 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 33.4277(8) _cell_length_b 6.1102(2) _cell_length_c 12.4082(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.375(2) _cell_angle_gamma 90.00 _cell_volume 2431.57(11) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 8116 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 31.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.807 _exptl_absorpt_correction_T_max 1.007 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 12156 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -48 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 31.01 _reflns_number_total 3828 _reflns_number_gt 2729 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0734P)^2^+0.3676P] 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 3828 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.1327 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 0.08895(3) 0.59533(16) 0.01008(7) 0.0262(2) Uani 1 1 d . . . N2 N 0.09147(3) 0.67727(17) 0.11573(8) 0.0334(2) Uani 1 1 d . . . N3 N 0.06690(3) 0.56027(18) 0.15649(8) 0.0322(2) Uani 1 1 d . . . N4 N 0.00050(3) 0.1046(2) 0.11991(9) 0.0411(3) Uani 1 1 d . . . N5 N 0.05296(3) 0.31554(18) -0.11273(8) 0.0356(3) Uani 1 1 d . . . H5A H 0.0647 0.3529 -0.1652 0.043 Uiso 1 1 calc R . . H5B H 0.0352 0.2060 -0.1241 0.043 Uiso 1 1 calc R . . C1 C 0.06215(3) 0.42526(18) -0.01564(8) 0.0248(2) Uani 1 1 d . . . C2 C 0.04823(3) 0.4023(2) 0.07976(8) 0.0271(2) Uani 1 1 d . . . C3 C 0.02155(3) 0.2405(2) 0.10240(8) 0.0301(3) Uani 1 1 d . . . C4 C 0.11610(3) 0.67745(18) -0.05204(8) 0.0261(2) Uani 1 1 d . . . C5 C 0.15818(3) 0.6185(2) -0.01935(9) 0.0286(2) Uani 1 1 d . . . C6 C 0.18284(4) 0.7033(2) -0.08341(10) 0.0372(3) Uani 1 1 d . . . H6 H 0.2117 0.6675 -0.0640 0.045 Uiso 1 1 calc R . . C7 C 0.16623(4) 0.8386(2) -0.17483(10) 0.0406(3) Uani 1 1 d . . . H7 H 0.1838 0.8938 -0.2169 0.049 Uiso 1 1 calc R . . C8 C 0.12459(4) 0.8937(2) -0.20529(10) 0.0393(3) Uani 1 1 d . . . H8 H 0.1134 0.9866 -0.2680 0.047 Uiso 1 1 calc R . . C9 C 0.09909(4) 0.8123(2) -0.14355(9) 0.0330(3) Uani 1 1 d . . . H9 H 0.0703 0.8485 -0.1638 0.040 Uiso 1 1 calc R . . C10 C 0.17687(4) 0.4704(2) 0.08049(9) 0.0341(3) Uani 1 1 d . . . H10 H 0.1537 0.4256 0.1121 0.041 Uiso 1 1 calc R . . C11 C 0.20840(7) 0.5933(4) 0.17145(15) 0.0867(8) Uani 1 1 d . . . H11A H 0.2192 0.4969 0.2363 0.130 Uiso 1 1 calc R . . H11B H 0.1950 0.7209 0.1943 0.130 Uiso 1 1 calc R . . H11C H 0.2314 0.6417 0.1428 0.130 Uiso 1 1 calc R . . C11' C 0.19445(10) 0.2656(4) 0.04498(18) 0.1058(10) Uani 1 1 d . . . H11D H 0.2044 0.1685 0.1099 0.159 Uiso 1 1 calc R . . H11E H 0.2177 0.3034 0.0151 0.159 Uiso 1 1 calc R . . H11F H 0.1727 0.1911 -0.0132 0.159 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 0.0296(4) 0.0296(5) 0.0212(4) -0.0024(3) 0.0098(3) -0.0032(4) N2 0.0404(5) 0.0376(6) 0.0254(4) -0.0084(4) 0.0143(4) -0.0066(4) N3 0.0354(5) 0.0376(6) 0.0262(4) -0.0043(4) 0.0128(4) -0.0037(4) N4 0.0466(6) 0.0482(7) 0.0338(5) -0.0049(5) 0.0201(4) -0.0127(5) N5 0.0467(6) 0.0387(6) 0.0254(4) -0.0070(4) 0.0167(4) -0.0161(5) C1 0.0257(5) 0.0268(6) 0.0226(4) 0.0009(4) 0.0078(4) 0.0002(4) C2 0.0278(5) 0.0319(6) 0.0229(5) -0.0005(4) 0.0094(4) -0.0003(4) C3 0.0306(5) 0.0400(7) 0.0218(5) -0.0013(4) 0.0108(4) -0.0012(5) C4 0.0305(5) 0.0255(5) 0.0243(5) -0.0025(4) 0.0110(4) -0.0045(4) C5 0.0305(5) 0.0289(6) 0.0273(5) -0.0014(4) 0.0098(4) -0.0041(5) C6 0.0340(6) 0.0425(8) 0.0384(6) 0.0004(5) 0.0154(5) -0.0057(5) C7 0.0496(7) 0.0422(8) 0.0363(6) 0.0015(5) 0.0227(5) -0.0109(6) C8 0.0534(7) 0.0349(7) 0.0303(6) 0.0061(5) 0.0130(5) -0.0036(6) C9 0.0367(6) 0.0320(6) 0.0299(5) 0.0021(4) 0.0088(4) 0.0012(5) C10 0.0307(5) 0.0372(7) 0.0332(6) 0.0043(5) 0.0072(4) 0.0005(5) C11 0.0960(14) 0.0885(15) 0.0488(9) 0.0230(9) -0.0232(9) -0.0452(12) C11' 0.190(3) 0.0749(15) 0.0630(12) 0.0242(11) 0.0523(15) 0.0763(17) _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 C1 1.3502(14) . ? N1 N2 1.3835(12) . ? N1 C4 1.4366(13) . ? N2 N3 1.2946(14) . ? N3 C2 1.3758(14) . ? N4 C3 1.1482(16) . ? N5 C1 1.3365(13) . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? C1 C2 1.3957(13) . ? C2 C3 1.4119(16) . ? C4 C9 1.3882(16) . ? C4 C5 1.3969(15) . ? C5 C6 1.3962(16) . ? C5 C10 1.5190(16) . ? C6 C7 1.3868(18) . ? C6 H6 0.9500 . ? C7 C8 1.3773(19) . ? C7 H7 0.9500 . ? C8 C9 1.3891(17) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11' 1.501(2) . ? C10 C11 1.509(2) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C11' H11D 0.9800 . ? C11' H11E 0.9800 . ? C11' H11F 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 C1 N1 N2 111.20(8) . . ? C1 N1 C4 128.27(9) . . ? N2 N1 C4 120.20(9) . . ? N3 N2 N1 107.13(9) . . ? N2 N3 C2 109.33(9) . . ? C1 N5 H5A 120.0 . . ? C1 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? N5 C1 N1 124.59(9) . . ? N5 C1 C2 131.85(10) . . ? N1 C1 C2 103.57(9) . . ? N3 C2 C1 108.77(9) . . ? N3 C2 C3 122.84(9) . . ? C1 C2 C3 128.28(10) . . ? N4 C3 C2 178.13(13) . . ? C9 C4 C5 122.50(10) . . ? C9 C4 N1 118.09(10) . . ? C5 C4 N1 119.40(10) . . ? C6 C5 C4 116.54(11) . . ? C6 C5 C10 120.82(10) . . ? C4 C5 C10 122.63(9) . . ? C7 C6 C5 121.49(12) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C8 C7 C6 120.72(11) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 119.41(11) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C4 C9 C8 119.34(11) . . ? C4 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C11' C10 C11 112.67(18) . . ? C11' C10 C5 111.25(11) . . ? C11 C10 C5 110.70(11) . . ? C11' C10 H10 107.3 . . ? C11 C10 H10 107.3 . . ? C5 C10 H10 107.3 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C11' H11D 109.5 . . ? C10 C11' H11E 109.5 . . ? H11D C11' H11E 109.5 . . ? C10 C11' H11F 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? 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 C1 N1 N2 N3 0.39(13) . . . . ? C4 N1 N2 N3 -173.57(10) . . . . ? N1 N2 N3 C2 0.09(13) . . . . ? N2 N1 C1 N5 178.99(11) . . . . ? C4 N1 C1 N5 -7.66(18) . . . . ? N2 N1 C1 C2 -0.67(12) . . . . ? C4 N1 C1 C2 172.67(10) . . . . ? N2 N3 C2 C1 -0.51(13) . . . . ? N2 N3 C2 C3 176.13(11) . . . . ? N5 C1 C2 N3 -178.92(12) . . . . ? N1 C1 C2 N3 0.71(12) . . . . ? N5 C1 C2 C3 4.7(2) . . . . ? N1 C1 C2 C3 -175.70(11) . . . . ? N3 C2 C3 N4 -128(4) . . . . ? C1 C2 C3 N4 48(4) . . . . ? C1 N1 C4 C9 80.03(15) . . . . ? N2 N1 C4 C9 -107.15(12) . . . . ? C1 N1 C4 C5 -99.49(13) . . . . ? N2 N1 C4 C5 73.32(14) . . . . ? C9 C4 C5 C6 0.30(17) . . . . ? N1 C4 C5 C6 179.81(10) . . . . ? C9 C4 C5 C10 -179.78(11) . . . . ? N1 C4 C5 C10 -0.28(16) . . . . ? C4 C5 C6 C7 -0.12(18) . . . . ? C10 C5 C6 C7 179.96(12) . . . . ? C5 C6 C7 C8 0.0(2) . . . . ? C6 C7 C8 C9 -0.1(2) . . . . ? C5 C4 C9 C8 -0.37(18) . . . . ? N1 C4 C9 C8 -179.88(11) . . . . ? C7 C8 C9 C4 0.24(19) . . . . ? C6 C5 C10 C11' -61.1(2) . . . . ? C4 C5 C10 C11' 118.97(18) . . . . ? C6 C5 C10 C11 64.97(17) . . . . ? C4 C5 C10 C11 -114.94(16) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 31.01 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.292 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.044 # Attachment 'sl1010.cif' data_sl1010 _database_code_depnum_ccdc_archive 'CCDC 791583' #TrackingRef 'sl1010.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H5 Br N6' _chemical_formula_sum 'C10 H5 Br N6' _chemical_formula_weight 289.11 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' Br Br -0.2901 2.4595 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2576(2) _cell_length_b 8.4262(2) _cell_length_c 8.8405(2) _cell_angle_alpha 97.305(1) _cell_angle_beta 110.101(1) _cell_angle_gamma 90.585(1) _cell_volume 502.74(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5799 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 32.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.910 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 4.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.613 _exptl_absorpt_correction_T_max 0.757 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 9286 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 32.02 _reflns_number_total 3475 _reflns_number_gt 3053 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0374P)^2^+0.2488P] 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 3475 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0811 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 Br1 Br 0.02984(3) 0.32350(2) 0.31503(2) 0.02511(7) Uani 1 1 d . . . N1 N -0.3249(2) 0.84892(17) -0.07837(18) 0.0195(3) Uani 1 1 d . . . N2 N -0.2912(3) 1.01096(18) -0.0353(2) 0.0256(3) Uani 1 1 d . . . N3 N -0.4130(3) 1.07523(19) -0.1549(2) 0.0253(3) Uani 1 1 d . . . N4 N -0.7837(3) 1.0286(2) -0.5330(2) 0.0361(4) Uani 1 1 d . . . N5 N -0.5284(2) 0.65817(18) -0.30058(18) 0.0206(3) Uani 1 1 d . . . N6 N -0.4968(3) 0.39128(19) -0.2895(2) 0.0274(4) Uani 1 1 d . . . H6A H -0.5835 0.3720 -0.3887 0.033 Uiso 1 1 calc R . . H6B H -0.4442 0.3112 -0.2377 0.033 Uiso 1 1 calc R . . C1 C -0.4687(3) 0.8092(2) -0.2269(2) 0.0192(3) Uani 1 1 d . . . C2 C -0.5247(3) 0.9583(2) -0.2733(2) 0.0217(3) Uani 1 1 d . . . C3 C -0.6702(3) 0.9953(2) -0.4175(2) 0.0253(4) Uani 1 1 d . . . C4 C -0.2351(3) 0.7326(2) 0.0162(2) 0.0190(3) Uani 1 1 d . . . C5 C -0.0912(3) 0.7726(2) 0.1704(2) 0.0227(3) Uani 1 1 d . . . H5B H -0.0491 0.8814 0.2131 0.027 Uiso 1 1 calc R . . C6 C -0.0115(3) 0.6508(2) 0.2595(2) 0.0230(3) Uani 1 1 d . . . H6C H 0.0868 0.6752 0.3642 0.028 Uiso 1 1 calc R . . C7 C -0.0765(3) 0.4915(2) 0.1945(2) 0.0200(3) Uani 1 1 d . . . C8 C -0.2164(3) 0.4514(2) 0.0409(2) 0.0195(3) Uani 1 1 d . . . H8A H -0.2565 0.3423 -0.0016 0.023 Uiso 1 1 calc R . . C9 C -0.2983(3) 0.5734(2) -0.0517(2) 0.0176(3) Uani 1 1 d . . . C10 C -0.4449(3) 0.5425(2) -0.2172(2) 0.0188(3) 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 Br1 0.02530(11) 0.02559(10) 0.02380(10) 0.01229(7) 0.00453(7) 0.00549(7) N1 0.0232(8) 0.0125(6) 0.0196(6) 0.0024(5) 0.0034(6) 0.0007(5) N2 0.0326(9) 0.0134(6) 0.0256(7) 0.0027(5) 0.0036(7) 0.0004(6) N3 0.0310(9) 0.0149(6) 0.0260(7) 0.0041(6) 0.0042(6) 0.0019(6) N4 0.0371(11) 0.0302(9) 0.0344(9) 0.0118(7) 0.0015(8) 0.0041(8) N5 0.0228(8) 0.0151(6) 0.0202(6) 0.0040(5) 0.0023(6) 0.0004(6) N6 0.0337(9) 0.0144(7) 0.0236(7) 0.0023(5) -0.0031(7) -0.0001(6) C1 0.0214(8) 0.0161(7) 0.0186(7) 0.0045(6) 0.0042(6) 0.0016(6) C2 0.0257(9) 0.0148(7) 0.0233(8) 0.0052(6) 0.0059(7) 0.0028(6) C3 0.0294(10) 0.0162(7) 0.0278(9) 0.0055(6) 0.0062(7) 0.0018(7) C4 0.0208(8) 0.0162(7) 0.0188(7) 0.0053(6) 0.0046(6) 0.0018(6) C5 0.0251(9) 0.0187(7) 0.0200(7) 0.0014(6) 0.0027(7) -0.0005(7) C6 0.0222(9) 0.0255(8) 0.0185(7) 0.0047(6) 0.0026(6) 0.0021(7) C7 0.0204(8) 0.0206(8) 0.0187(7) 0.0079(6) 0.0045(6) 0.0032(6) C8 0.0210(8) 0.0161(7) 0.0206(7) 0.0069(6) 0.0047(6) 0.0032(6) C9 0.0199(8) 0.0149(7) 0.0169(7) 0.0041(5) 0.0044(6) 0.0022(6) C10 0.0209(8) 0.0146(7) 0.0193(7) 0.0035(6) 0.0044(6) 0.0000(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 Br1 C7 1.8910(17) . ? N1 C1 1.365(2) . ? N1 N2 1.366(2) . ? N1 C4 1.390(2) . ? N2 N3 1.306(2) . ? N3 C2 1.365(2) . ? N4 C3 1.140(3) . ? N5 C10 1.322(2) . ? N5 C1 1.347(2) . ? N6 C10 1.338(2) . ? N6 H6A 0.8800 . ? N6 H6B 0.8800 . ? C1 C2 1.393(2) . ? C2 C3 1.421(3) . ? C4 C5 1.400(2) . ? C4 C9 1.401(2) . ? C5 C6 1.383(3) . ? C5 H5B 0.9500 . ? C6 C7 1.400(3) . ? C6 H6C 0.9500 . ? C7 C8 1.385(2) . ? C8 C9 1.404(2) . ? C8 H8A 0.9500 . ? C9 C10 1.473(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 C1 N1 N2 112.23(14) . . ? C1 N1 C4 121.53(15) . . ? N2 N1 C4 126.17(15) . . ? N3 N2 N1 106.07(15) . . ? N2 N3 C2 110.10(15) . . ? C10 N5 C1 116.15(15) . . ? C10 N6 H6A 120.0 . . ? C10 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? N5 C1 N1 124.78(15) . . ? N5 C1 C2 132.58(17) . . ? N1 C1 C2 102.63(15) . . ? N3 C2 C1 108.96(16) . . ? N3 C2 C3 121.82(16) . . ? C1 C2 C3 129.22(17) . . ? N4 C3 C2 178.1(2) . . ? N1 C4 C5 121.87(16) . . ? N1 C4 C9 115.95(15) . . ? C5 C4 C9 122.17(16) . . ? C6 C5 C4 118.77(17) . . ? C6 C5 H5B 120.6 . . ? C4 C5 H5B 120.6 . . ? C5 C6 C7 119.61(17) . . ? C5 C6 H6C 120.2 . . ? C7 C6 H6C 120.2 . . ? C8 C7 C6 121.75(16) . . ? C8 C7 Br1 118.02(13) . . ? C6 C7 Br1 120.21(13) . . ? C7 C8 C9 119.41(17) . . ? C7 C8 H8A 120.3 . . ? C9 C8 H8A 120.3 . . ? C4 C9 C8 118.26(16) . . ? C4 C9 C10 118.38(15) . . ? C8 C9 C10 123.35(16) . . ? N5 C10 N6 117.46(16) . . ? N5 C10 C9 122.99(16) . . ? N6 C10 C9 119.55(15) . . ? 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 C1 N1 N2 N3 0.3(2) . . . . ? C4 N1 N2 N3 -176.66(18) . . . . ? N1 N2 N3 C2 0.3(2) . . . . ? C10 N5 C1 N1 2.9(3) . . . . ? C10 N5 C1 C2 -178.2(2) . . . . ? N2 N1 C1 N5 178.44(18) . . . . ? C4 N1 C1 N5 -4.5(3) . . . . ? N2 N1 C1 C2 -0.7(2) . . . . ? C4 N1 C1 C2 176.40(17) . . . . ? N2 N3 C2 C1 -0.8(2) . . . . ? N2 N3 C2 C3 179.8(2) . . . . ? N5 C1 C2 N3 -178.2(2) . . . . ? N1 C1 C2 N3 0.8(2) . . . . ? N5 C1 C2 C3 1.2(4) . . . . ? N1 C1 C2 C3 -179.8(2) . . . . ? N3 C2 C3 N4 34(7) . . . . ? C1 C2 C3 N4 -145(7) . . . . ? C1 N1 C4 C5 -178.29(18) . . . . ? N2 N1 C4 C5 -1.6(3) . . . . ? C1 N1 C4 C9 1.2(3) . . . . ? N2 N1 C4 C9 177.89(18) . . . . ? N1 C4 C5 C6 178.41(18) . . . . ? C9 C4 C5 C6 -1.1(3) . . . . ? C4 C5 C6 C7 -0.3(3) . . . . ? C5 C6 C7 C8 1.5(3) . . . . ? C5 C6 C7 Br1 -179.70(15) . . . . ? C6 C7 C8 C9 -1.2(3) . . . . ? Br1 C7 C8 C9 179.96(14) . . . . ? N1 C4 C9 C8 -178.16(16) . . . . ? C5 C4 C9 C8 1.4(3) . . . . ? N1 C4 C9 C10 2.8(3) . . . . ? C5 C4 C9 C10 -177.68(18) . . . . ? C7 C8 C9 C4 -0.2(3) . . . . ? C7 C8 C9 C10 178.77(17) . . . . ? C1 N5 C10 N6 -177.93(18) . . . . ? C1 N5 C10 C9 1.5(3) . . . . ? C4 C9 C10 N5 -4.4(3) . . . . ? C8 C9 C10 N5 176.60(18) . . . . ? C4 C9 C10 N6 175.02(19) . . . . ? C8 C9 C10 N6 -4.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 32.02 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.495 _refine_diff_density_min -0.865 _refine_diff_density_rms 0.098