# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _publ_contact_author_name 'Prof. Brenno Neto' _publ_contact_author_address ;University of Brasilia - Chemistry Institute - IQ-UnB Campus Universit\'ario Darcy Ribeiro CEP 70904-970 - P.O.Box 4478 - Bras\'ilia - DF - Brazil ; _publ_contact_author_email brenno.ipi@gmail.com _publ_contact_author_phone 55(61)31073867 _publ_contact_author_fax 55(61)32734149 loop_ _publ_author_address ;University of Brasilia - Chemistry Institute - IQ-UnB Campus Universit\'ario Darcy Ribeiro CEP 70904-970 - P.O.Box 4478 - Bras\'ilia - DF - Brazil ; _publ_author_name B.A.Neto data_shelxl _database_code_depnum_ccdc_archive 'CCDC 842632' #TrackingRef 'Deposit_06.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'C11 H7 Br N4 S' _chemical_melting_point ? _chemical_formula_moiety 'C11 H7 Br N4 S' _chemical_formula_sum 'C11 H7 Br N4 S' _chemical_formula_weight 307.18 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.3849(3) _cell_length_b 23.419(2) _cell_length_c 11.2403(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.743(6) _cell_angle_gamma 90.00 _cell_volume 1134.03(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1743 _cell_measurement_theta_min 2.5352 _cell_measurement_theta_max 23.6157 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.799 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 3.789 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.60 _exptl_absorpt_correction_T_max 0.72 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; 'Walker, N.; Shuart, D.; Acta Crystallogr., 1983, A59, 158.' ; _diffrn_ambient_temperature 296(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 'Bruker CCD Smart APEX II' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10203 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2607 _reflns_number_gt 1648 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Instrument Service v2011.2.0.0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 2008)' _computing_publication_material 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0284P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2607 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0755 _refine_ls_wR_factor_gt 0.0644 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 1.27065(8) 0.530487(15) 0.83139(3) 0.05051(16) Uani 1 1 d . . . S2 S 1.31548(19) 0.42786(4) 0.46478(7) 0.0432(2) Uani 1 1 d . . . N16 N 0.5264(6) 0.25666(12) 0.7602(2) 0.0426(7) Uani 1 1 d . . . C13 C 0.3423(9) 0.16739(16) 0.5991(4) 0.0532(10) Uani 1 1 d . . . C11 C 0.6050(7) 0.25543(14) 0.6522(3) 0.0360(8) Uani 1 1 d . . . C12 C 0.5176(8) 0.21148(15) 0.5683(3) 0.0444(9) Uani 1 1 d . . . C14 C 0.2572(9) 0.16781(18) 0.7108(4) 0.0572(11) Uani 1 1 d . . . C15 C 0.3515(9) 0.21309(17) 0.7869(3) 0.0518(10) Uani 1 1 d . . . N1 N 1.3244(6) 0.46869(11) 0.5814(2) 0.0384(6) Uani 1 1 d . . . N3 N 1.1225(5) 0.37410(11) 0.5022(2) 0.0379(7) Uani 1 1 d . . . C8 C 1.1717(6) 0.44057(14) 0.6568(3) 0.0320(7) Uani 1 1 d . . . C9 C 1.0547(6) 0.38663(13) 0.6110(3) 0.0310(7) Uani 1 1 d . . . N10 N 0.7826(6) 0.29956(12) 0.6197(3) 0.0403(7) Uani 1 1 d . . . C7 C 1.1138(7) 0.45900(13) 0.7705(3) 0.0354(8) Uani 1 1 d . . . C6 C 0.9484(8) 0.42447(15) 0.8306(3) 0.0393(8) Uani 1 1 d . . . C5 C 0.8307(8) 0.37048(15) 0.7849(3) 0.0396(8) Uani 1 1 d . . . C4 C 0.8815(7) 0.35031(13) 0.6768(3) 0.0329(7) Uani 1 1 d . . . H5 H 0.719(6) 0.3466(14) 0.828(2) 0.043(9) Uiso 1 1 d . . . H6 H 0.920(6) 0.4356(13) 0.906(3) 0.039(9) Uiso 1 1 d . . . H14 H 0.138(7) 0.1394(15) 0.733(3) 0.056(11) Uiso 1 1 d . . . H15 H 0.313(7) 0.2115(15) 0.873(3) 0.066(11) Uiso 1 1 d . . . H10 H 0.826(6) 0.2960(13) 0.556(3) 0.033(10) Uiso 1 1 d . . . H12 H 0.600(7) 0.2132(14) 0.494(3) 0.052(10) Uiso 1 1 d . . . H13 H 0.298(8) 0.1368(17) 0.542(3) 0.080(13) 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 Br1 0.0660(3) 0.0352(2) 0.0494(2) -0.00908(17) 0.00841(17) -0.0043(2) S2 0.0519(5) 0.0423(6) 0.0394(5) -0.0013(4) 0.0186(4) -0.0061(4) N16 0.0533(17) 0.0398(18) 0.0363(16) -0.0008(13) 0.0123(13) -0.0119(14) C13 0.065(2) 0.030(2) 0.057(3) 0.001(2) -0.009(2) -0.003(2) C11 0.0391(18) 0.0279(19) 0.0400(19) 0.0016(15) 0.0046(15) 0.0005(15) C12 0.057(2) 0.032(2) 0.043(2) 0.0008(17) 0.0060(18) -0.0005(18) C14 0.063(3) 0.048(3) 0.054(3) 0.014(2) -0.004(2) -0.024(2) C15 0.062(2) 0.054(3) 0.039(2) 0.0082(19) 0.0079(18) -0.018(2) N1 0.0425(14) 0.0369(16) 0.0374(15) 0.0016(13) 0.0115(12) -0.0026(14) N3 0.0426(15) 0.0363(17) 0.0373(15) -0.0031(12) 0.0144(12) -0.0045(13) C8 0.0326(17) 0.0300(18) 0.0327(18) 0.0053(14) 0.0041(14) 0.0025(14) C9 0.0305(16) 0.0284(18) 0.0345(18) -0.0011(14) 0.0072(14) 0.0049(14) N10 0.0557(19) 0.0328(17) 0.0372(17) -0.0040(14) 0.0212(14) -0.0075(14) C7 0.0423(18) 0.0279(19) 0.0354(18) -0.0028(14) 0.0055(15) 0.0020(15) C6 0.055(2) 0.039(2) 0.0262(18) -0.0013(16) 0.0125(16) 0.0082(18) C5 0.0469(19) 0.035(2) 0.040(2) 0.0041(17) 0.0164(16) -0.0028(17) C4 0.0362(17) 0.0277(18) 0.0356(18) 0.0017(14) 0.0085(14) 0.0022(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C7 1.889(3) . ? S2 N3 1.616(3) . ? S2 N1 1.617(3) . ? N16 C11 1.323(4) . ? N16 C15 1.344(4) . ? C13 C12 1.370(5) . ? C13 C14 1.374(5) . ? C13 H13 0.96(4) . ? C11 N10 1.383(4) . ? C11 C12 1.400(4) . ? C12 H12 0.97(3) . ? C14 C15 1.377(5) . ? C14 H14 0.91(3) . ? C15 H15 1.01(3) . ? N1 C8 1.346(4) . ? N3 C9 1.344(3) . ? C8 C7 1.416(4) . ? C8 C9 1.423(4) . ? C9 C4 1.434(4) . ? N10 C4 1.382(4) . ? N10 H10 0.78(3) . ? C7 C6 1.349(4) . ? C6 C5 1.425(5) . ? C6 H6 0.92(3) . ? C5 C4 1.360(4) . ? C5 H5 0.94(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 S2 N1 100.64(13) . . ? C11 N16 C15 116.5(3) . . ? C12 C13 C14 119.1(4) . . ? C12 C13 H13 116(2) . . ? C14 C13 H13 124(2) . . ? N16 C11 N10 118.8(3) . . ? N16 C11 C12 123.3(3) . . ? N10 C11 C12 117.9(3) . . ? C13 C12 C11 118.7(4) . . ? C13 C12 H12 124.4(19) . . ? C11 C12 H12 116.8(19) . . ? C13 C14 C15 118.2(4) . . ? C13 C14 H14 121(2) . . ? C15 C14 H14 121(2) . . ? N16 C15 C14 124.3(4) . . ? N16 C15 H15 116(2) . . ? C14 C15 H15 119(2) . . ? C8 N1 S2 106.3(2) . . ? C9 N3 S2 106.4(2) . . ? N1 C8 C7 127.8(3) . . ? N1 C8 C9 113.2(3) . . ? C7 C8 C9 118.9(3) . . ? N3 C9 C8 113.4(3) . . ? N3 C9 C4 124.6(3) . . ? C8 C9 C4 122.0(3) . . ? C4 N10 C11 131.5(3) . . ? C4 N10 H10 114(2) . . ? C11 N10 H10 114(2) . . ? C6 C7 C8 118.2(3) . . ? C6 C7 Br1 122.9(2) . . ? C8 C7 Br1 118.9(2) . . ? C7 C6 C5 122.9(3) . . ? C7 C6 H6 118.1(19) . . ? C5 C6 H6 118.9(19) . . ? C4 C5 C6 121.5(3) . . ? C4 C5 H5 116.3(19) . . ? C6 C5 H5 122.2(19) . . ? C5 C4 N10 128.6(3) . . ? C5 C4 C9 116.4(3) . . ? N10 C4 C9 114.9(3) . . ? 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 C15 N16 C11 N10 179.4(3) . . . . ? C15 N16 C11 C12 -0.7(5) . . . . ? C14 C13 C12 C11 0.2(5) . . . . ? N16 C11 C12 C13 -0.1(5) . . . . ? N10 C11 C12 C13 179.9(3) . . . . ? C12 C13 C14 C15 0.4(6) . . . . ? C11 N16 C15 C14 1.3(5) . . . . ? C13 C14 C15 N16 -1.2(6) . . . . ? N3 S2 N1 C8 0.2(2) . . . . ? N1 S2 N3 C9 0.2(2) . . . . ? S2 N1 C8 C7 -179.2(3) . . . . ? S2 N1 C8 C9 -0.5(3) . . . . ? S2 N3 C9 C8 -0.5(3) . . . . ? S2 N3 C9 C4 179.4(2) . . . . ? N1 C8 C9 N3 0.7(4) . . . . ? C7 C8 C9 N3 179.5(2) . . . . ? N1 C8 C9 C4 -179.2(2) . . . . ? C7 C8 C9 C4 -0.4(4) . . . . ? N16 C11 N10 C4 -6.2(5) . . . . ? C12 C11 N10 C4 173.9(3) . . . . ? N1 C8 C7 C6 178.4(3) . . . . ? C9 C8 C7 C6 -0.2(4) . . . . ? N1 C8 C7 Br1 -1.6(4) . . . . ? C9 C8 C7 Br1 179.8(2) . . . . ? C8 C7 C6 C5 0.1(5) . . . . ? Br1 C7 C6 C5 -179.8(2) . . . . ? C7 C6 C5 C4 0.5(5) . . . . ? C6 C5 C4 N10 -179.4(3) . . . . ? C6 C5 C4 C9 -1.0(5) . . . . ? C11 N10 C4 C5 0.9(6) . . . . ? C11 N10 C4 C9 -177.6(3) . . . . ? N3 C9 C4 C5 -178.9(3) . . . . ? C8 C9 C4 C5 0.9(4) . . . . ? N3 C9 C4 N10 -0.2(4) . . . . ? C8 C9 C4 N10 179.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N10 H10 N3 0.78(3) 2.39(3) 2.783(4) 113(3) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.310 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.073 # Attachment 'Deposit_08.cif' data_08 _database_code_depnum_ccdc_archive 'CCDC 842633' #TrackingRef 'Deposit_08.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'C11 H8 N4 S' _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 N4 S' _chemical_formula_sum 'C11 H8 N4 S' _chemical_formula_weight 228.27 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 22.9294(8) _cell_length_b 3.8241(2) _cell_length_c 23.2133(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.832(2) _cell_angle_gamma 90.00 _cell_volume 2030.89(15) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2928 _cell_measurement_theta_min 2.4175 _cell_measurement_theta_max 19.7962 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.292 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; 'Walker, N.; Shuart, D.; Acta Crystallogr., 1983, A59, 158.' ; _diffrn_ambient_temperature 296(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 'Bruker CCD Smart APEX II' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24791 _diffrn_reflns_av_R_equivalents 0.1326 _diffrn_reflns_av_sigmaI/netI 0.1520 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 26.67 _reflns_number_total 4259 _reflns_number_gt 1909 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Instrument Service v2011.2.0.0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 2008)' _computing_publication_material 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0494P)^2^+6.9398P] 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 SHELXL _refine_ls_extinction_coef 0.0075(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4259 _refine_ls_number_parameters 330 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1956 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1872 _refine_ls_wR_factor_gt 0.1270 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.930 _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 S2 S 0.17895(6) 1.3224(4) 0.32778(5) 0.0523(4) Uani 1 1 d . . . S2' S 0.17224(6) 0.6897(5) 1.17986(5) 0.0612(5) Uani 1 1 d . . . N3 N 0.12393(15) 1.1537(12) 0.29112(14) 0.0434(11) Uani 1 1 d . . . N10 N 0.01742(17) 0.8320(12) 0.25675(15) 0.0445(11) Uani 1 1 d . . . N1 N 0.15661(18) 1.3089(12) 0.39193(16) 0.0487(11) Uani 1 1 d . . . N10' N 0.24414(18) 0.8043(13) 1.01171(17) 0.0477(11) Uani 1 1 d . . . N3' N 0.20865(17) 0.6998(12) 1.12296(15) 0.0498(11) Uani 1 1 d . . . N16' N 0.24595(17) 0.9796(13) 0.91481(16) 0.0509(12) Uani 1 1 d . . . N1' N 0.11122(16) 0.8528(13) 1.15594(17) 0.0550(12) Uani 1 1 d . . . C15 C -0.1307(2) 0.5692(18) 0.2265(3) 0.0625(17) Uani 1 1 d . . . C11 C -0.0340(2) 0.6954(14) 0.22867(18) 0.0420(12) Uani 1 1 d . . . C8 C 0.1024(2) 1.1618(13) 0.38673(18) 0.0388(11) Uani 1 1 d . . . N16 N -0.08250(17) 0.6917(13) 0.25643(17) 0.0542(12) Uani 1 1 d . . . C4 C 0.02844(19) 0.9141(13) 0.31435(18) 0.0376(12) Uani 1 1 d . . . C15' C 0.2774(3) 1.0060(18) 0.8682(2) 0.0601(16) Uani 1 1 d . . . C11' C 0.2735(2) 0.8320(14) 0.96145(19) 0.0427(12) Uani 1 1 d . . . C4' C 0.1878(2) 0.9007(13) 1.02305(19) 0.0423(12) Uani 1 1 d . . . C5 C -0.0054(2) 0.8556(14) 0.35878(19) 0.0478(13) Uani 1 1 d . . . H5 H -0.0422 0.7568 0.3515 0.057 Uiso 1 1 calc R . . C9 C 0.0840(2) 1.0751(13) 0.32872(18) 0.0392(11) Uani 1 1 d . . . C7' C 0.0732(2) 1.0745(15) 1.0597(2) 0.0540(14) Uani 1 1 d . . . H7' H 0.0360 1.1283 1.0705 0.065 Uiso 1 1 calc R . . C6' C 0.0893(2) 1.1331(15) 1.0054(2) 0.0530(14) Uani 1 1 d . . . H6' H 0.0620 1.2336 0.9790 0.064 Uiso 1 1 calc R . . C13 C -0.0800(3) 0.4498(16) 0.1442(2) 0.0568(15) Uani 1 1 d . . . C14' C 0.3338(3) 0.8921(17) 0.8655(2) 0.0634(17) Uani 1 1 d . . . C12' C 0.3302(2) 0.7101(16) 0.9634(2) 0.0482(14) Uani 1 1 d . . . C7 C 0.0661(2) 1.0941(15) 0.4317(2) 0.0495(14) Uani 1 1 d . . . H7 H 0.0773 1.1511 0.4698 0.059 Uiso 1 1 calc R . . C8' C 0.1164(2) 0.9260(15) 1.09923(19) 0.0474(13) Uani 1 1 d . . . C9' C 0.17286(19) 0.8389(14) 1.08088(18) 0.0402(12) Uani 1 1 d . . . C6 C 0.0142(2) 0.9421(16) 0.4169(2) 0.0561(15) Uani 1 1 d . . . H6 H -0.0103 0.8905 0.4461 0.067 Uiso 1 1 calc R . . C5' C 0.1450(2) 1.0508(14) 0.9866(2) 0.0489(13) Uani 1 1 d . . . H5' H 0.1530 1.0991 0.9486 0.059 Uiso 1 1 calc R . . C13' C 0.3609(3) 0.7398(17) 0.9148(2) 0.0572(16) Uani 1 1 d . . . C12 C -0.0304(2) 0.5737(15) 0.1726(2) 0.0485(14) Uani 1 1 d . . . C14 C -0.1314(3) 0.4504(18) 0.1714(3) 0.0624(17) Uani 1 1 d . . . H10' H 0.264(2) 0.694(15) 1.040(2) 0.070(19) Uiso 1 1 d . . . H12' H 0.3497(19) 0.610(13) 0.9981(19) 0.050(14) Uiso 1 1 d . . . H12 H 0.0085(19) 0.557(12) 0.1546(17) 0.042(13) Uiso 1 1 d . . . H10 H 0.047(2) 0.865(13) 0.2310(19) 0.051(15) Uiso 1 1 d . . . H14' H 0.357(3) 0.927(18) 0.829(3) 0.11(2) Uiso 1 1 d . . . H13 H -0.076(2) 0.362(14) 0.107(2) 0.063(16) Uiso 1 1 d . . . H15 H -0.1657(19) 0.568(13) 0.2518(18) 0.048(14) Uiso 1 1 d . . . H15' H 0.257(2) 1.119(15) 0.835(2) 0.071(17) Uiso 1 1 d . . . H13' H 0.402(2) 0.669(13) 0.9148(19) 0.055(15) Uiso 1 1 d . . . H14 H -0.165(2) 0.367(16) 0.153(2) 0.08(2) 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 S2 0.0479(8) 0.0662(10) 0.0422(7) -0.0045(7) -0.0013(6) -0.0091(8) S2' 0.0545(9) 0.0888(12) 0.0406(7) 0.0081(8) 0.0048(6) 0.0001(9) N3 0.035(2) 0.063(3) 0.0317(18) -0.004(2) -0.0011(16) -0.007(2) N10 0.040(2) 0.062(3) 0.0311(19) -0.007(2) -0.0021(17) -0.006(2) N1 0.055(3) 0.050(3) 0.040(2) -0.002(2) -0.0015(19) -0.003(2) N10' 0.040(2) 0.065(3) 0.038(2) 0.003(2) 0.0040(19) 0.004(2) N3' 0.052(3) 0.060(3) 0.036(2) 0.004(2) 0.0001(18) -0.001(2) N16' 0.042(2) 0.068(3) 0.042(2) 0.002(2) -0.0011(19) -0.007(2) N1' 0.037(2) 0.080(3) 0.049(2) -0.003(3) 0.0041(18) 0.004(3) C15 0.041(3) 0.086(5) 0.059(3) -0.002(4) -0.007(3) -0.011(4) C11 0.048(3) 0.043(3) 0.035(2) 0.000(2) -0.003(2) 0.000(3) C8 0.038(3) 0.045(3) 0.033(2) 0.000(2) 0.0023(19) -0.001(3) N16 0.042(2) 0.073(3) 0.047(2) -0.005(3) 0.0010(19) -0.006(3) C4 0.031(2) 0.048(3) 0.032(2) -0.002(2) -0.0048(19) 0.001(2) C15' 0.060(4) 0.080(5) 0.040(3) 0.006(3) 0.004(3) -0.015(4) C11' 0.041(3) 0.051(3) 0.035(2) -0.005(3) -0.004(2) -0.006(3) C4' 0.044(3) 0.047(3) 0.036(2) -0.004(2) 0.001(2) -0.001(3) C5 0.040(3) 0.059(4) 0.044(3) 0.002(3) 0.004(2) -0.004(3) C9 0.042(3) 0.042(3) 0.034(2) 0.003(2) 0.000(2) 0.003(3) C7' 0.045(3) 0.060(4) 0.056(3) -0.006(3) -0.003(2) 0.003(3) C6' 0.052(3) 0.061(4) 0.045(3) 0.001(3) -0.004(2) 0.008(3) C13 0.070(4) 0.057(4) 0.042(3) -0.004(3) -0.009(3) -0.003(3) C14' 0.072(4) 0.070(4) 0.049(3) -0.005(3) 0.014(3) -0.019(4) C12' 0.037(3) 0.062(4) 0.045(3) 0.001(3) -0.001(2) 0.003(3) C7 0.043(3) 0.067(4) 0.037(2) -0.002(3) -0.008(2) 0.000(3) C8' 0.051(3) 0.057(3) 0.035(2) -0.010(3) 0.009(2) -0.008(3) C9' 0.037(3) 0.050(3) 0.034(2) -0.005(2) 0.0040(19) -0.006(3) C6 0.060(3) 0.070(4) 0.038(3) 0.005(3) 0.006(2) 0.001(3) C5' 0.052(3) 0.056(3) 0.037(2) 0.000(3) -0.005(2) 0.001(3) C13' 0.045(3) 0.066(4) 0.061(3) -0.006(3) 0.015(3) -0.001(3) C12 0.040(3) 0.064(4) 0.040(3) -0.006(3) -0.007(2) 0.001(3) C14 0.055(4) 0.070(4) 0.060(4) 0.001(3) -0.014(3) -0.014(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 S2 N1 1.608(4) . ? S2 N3 1.609(4) . ? S2' N1' 1.597(4) . ? S2' N3' 1.610(4) . ? N3 C9 1.340(5) . ? N10 C4 1.380(5) . ? N10 C11 1.410(6) . ? N10 H10 0.95(4) . ? N1 C8 1.362(6) . ? N10' C4' 1.385(6) . ? N10' C11' 1.390(6) . ? N10' H10' 0.88(5) . ? N3' C9' 1.343(6) . ? N16' C11' 1.341(6) . ? N16' C15' 1.345(6) . ? N1' C8' 1.359(6) . ? C15 N16 1.348(6) . ? C15 C14 1.356(8) . ? C15 H15 1.03(4) . ? C11 N16 1.321(6) . ? C11 C12 1.389(6) . ? C8 C7 1.403(6) . ? C8 C9 1.423(6) . ? C4 C5 1.349(6) . ? C4 C9 1.434(6) . ? C15' C14' 1.369(8) . ? C15' H15' 0.98(5) . ? C11' C12' 1.378(6) . ? C4' C5' 1.378(6) . ? C4' C9' 1.427(6) . ? C5 C6 1.432(6) . ? C5 H5 0.9300 . ? C7' C6' 1.353(6) . ? C7' C8' 1.423(7) . ? C7' H7' 0.9300 . ? C6' C5' 1.414(7) . ? C6' H6' 0.9300 . ? C13 C12 1.361(7) . ? C13 C14 1.374(8) . ? C13 H13 0.94(5) . ? C14' C13' 1.393(8) . ? C14' H14' 1.04(6) . ? C12' C13' 1.373(7) . ? C12' H12' 0.98(4) . ? C7 C6 1.349(7) . ? C7 H7 0.9300 . ? C8' C9' 1.428(6) . ? C6 H6 0.9300 . ? C5' H5' 0.9300 . ? C13' H13' 0.98(5) . ? C12 H12 1.01(4) . ? C14 H14 0.91(6) . ? 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 N1 S2 N3 100.9(2) . . ? N1' S2' N3' 101.3(2) . . ? C9 N3 S2 106.9(3) . . ? C4 N10 C11 128.7(4) . . ? C4 N10 H10 119(3) . . ? C11 N10 H10 112(3) . . ? C8 N1 S2 106.0(3) . . ? C4' N10' C11' 130.5(4) . . ? C4' N10' H10' 116(3) . . ? C11' N10' H10' 114(3) . . ? C9' N3' S2' 106.3(3) . . ? C11' N16' C15' 115.6(5) . . ? C8' N1' S2' 106.6(3) . . ? N16 C15 C14 124.1(6) . . ? N16 C15 H15 111(2) . . ? C14 C15 H15 125(3) . . ? N16 C11 C12 123.9(4) . . ? N16 C11 N10 118.9(4) . . ? C12 C11 N10 117.1(4) . . ? N1 C8 C7 126.4(4) . . ? N1 C8 C9 113.0(4) . . ? C7 C8 C9 120.6(4) . . ? C11 N16 C15 116.0(4) . . ? C5 C4 N10 128.7(4) . . ? C5 C4 C9 116.1(4) . . ? N10 C4 C9 115.2(4) . . ? N16' C15' C14' 124.9(6) . . ? N16' C15' H15' 114(3) . . ? C14' C15' H15' 121(3) . . ? N16' C11' C12' 124.1(4) . . ? N16' C11' N10' 118.7(4) . . ? C12' C11' N10' 117.1(4) . . ? C5' C4' N10' 129.0(4) . . ? C5' C4' C9' 116.1(4) . . ? N10' C4' C9' 114.9(4) . . ? C4 C5 C6 121.4(5) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? N3 C9 C8 113.0(4) . . ? N3 C9 C4 125.4(4) . . ? C8 C9 C4 121.5(4) . . ? C6' C7' C8' 116.5(5) . . ? C6' C7' H7' 121.8 . . ? C8' C7' H7' 121.8 . . ? C7' C6' C5' 123.9(5) . . ? C7' C6' H6' 118.0 . . ? C5' C6' H6' 118.0 . . ? C12 C13 C14 119.4(5) . . ? C12 C13 H13 116(3) . . ? C14 C13 H13 124(3) . . ? C15' C14' C13' 117.8(5) . . ? C15' C14' H14' 122(4) . . ? C13' C14' H14' 121(4) . . ? C13' C12' C11' 118.6(5) . . ? C13' C12' H12' 119(3) . . ? C11' C12' H12' 123(3) . . ? C6 C7 C8 116.5(4) . . ? C6 C7 H7 121.7 . . ? C8 C7 H7 121.7 . . ? N1' C8' C7' 127.2(5) . . ? N1' C8' C9' 112.4(4) . . ? C7' C8' C9' 120.4(4) . . ? N3' C9' C4' 125.2(4) . . ? N3' C9' C8' 113.4(4) . . ? C4' C9' C8' 121.4(4) . . ? C7 C6 C5 123.8(5) . . ? C7 C6 H6 118.1 . . ? C5 C6 H6 118.1 . . ? C4' C5' C6' 121.6(4) . . ? C4' C5' H5' 119.2 . . ? C6' C5' H5' 119.2 . . ? C12' C13' C14' 119.0(6) . . ? C12' C13' H13' 121(3) . . ? C14' C13' H13' 119(3) . . ? C13 C12 C11 118.0(5) . . ? C13 C12 H12 120(2) . . ? C11 C12 H12 121(2) . . ? C15 C14 C13 118.5(5) . . ? C15 C14 H14 120(4) . . ? C13 C14 H14 121(4) . . ? 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 N1 S2 N3 C9 -0.1(4) . . . . ? N3 S2 N1 C8 0.4(4) . . . . ? N1' S2' N3' C9' 0.2(4) . . . . ? N3' S2' N1' C8' 0.2(4) . . . . ? C4 N10 C11 N16 12.3(8) . . . . ? C4 N10 C11 C12 -168.1(5) . . . . ? S2 N1 C8 C7 179.4(5) . . . . ? S2 N1 C8 C9 -0.5(5) . . . . ? C12 C11 N16 C15 -1.8(8) . . . . ? N10 C11 N16 C15 177.7(5) . . . . ? C14 C15 N16 C11 0.7(9) . . . . ? C11 N10 C4 C5 6.4(9) . . . . ? C11 N10 C4 C9 -175.3(5) . . . . ? C11' N16' C15' C14' 0.6(9) . . . . ? C15' N16' C11' C12' -0.3(8) . . . . ? C15' N16' C11' N10' 178.4(5) . . . . ? C4' N10' C11' N16' 1.4(9) . . . . ? C4' N10' C11' C12' -179.8(5) . . . . ? C11' N10' C4' C5' 0.5(9) . . . . ? C11' N10' C4' C9' -178.6(5) . . . . ? N10 C4 C5 C6 176.7(5) . . . . ? C9 C4 C5 C6 -1.5(8) . . . . ? S2 N3 C9 C8 -0.1(5) . . . . ? S2 N3 C9 C4 -179.0(4) . . . . ? N1 C8 C9 N3 0.4(6) . . . . ? C7 C8 C9 N3 -179.4(5) . . . . ? N1 C8 C9 C4 179.3(4) . . . . ? C7 C8 C9 C4 -0.5(8) . . . . ? C5 C4 C9 N3 179.7(5) . . . . ? N10 C4 C9 N3 1.2(7) . . . . ? C5 C4 C9 C8 1.0(7) . . . . ? N10 C4 C9 C8 -177.5(5) . . . . ? C8' C7' C6' C5' 1.1(9) . . . . ? N16' C15' C14' C13' -0.5(10) . . . . ? N16' C11' C12' C13' 0.0(9) . . . . ? N10' C11' C12' C13' -178.8(5) . . . . ? N1 C8 C7 C6 -179.2(5) . . . . ? C9 C8 C7 C6 0.6(8) . . . . ? S2' N1' C8' C7' 179.9(5) . . . . ? S2' N1' C8' C9' -0.6(6) . . . . ? C6' C7' C8' N1' 178.1(6) . . . . ? C6' C7' C8' C9' -1.4(8) . . . . ? S2' N3' C9' C4' 179.1(4) . . . . ? S2' N3' C9' C8' -0.5(6) . . . . ? C5' C4' C9' N3' -179.1(5) . . . . ? N10' C4' C9' N3' 0.1(8) . . . . ? C5' C4' C9' C8' 0.5(7) . . . . ? N10' C4' C9' C8' 179.7(5) . . . . ? N1' C8' C9' N3' 0.7(7) . . . . ? C7' C8' C9' N3' -179.7(5) . . . . ? N1' C8' C9' C4' -178.9(5) . . . . ? C7' C8' C9' C4' 0.7(8) . . . . ? C8 C7 C6 C5 -1.2(9) . . . . ? C4 C5 C6 C7 1.8(9) . . . . ? N10' C4' C5' C6' 180.0(5) . . . . ? C9' C4' C5' C6' -0.9(8) . . . . ? C7' C6' C5' C4' 0.1(9) . . . . ? C11' C12' C13' C14' 0.1(9) . . . . ? C15' C14' C13' C12' 0.1(9) . . . . ? C14 C13 C12 C11 0.2(9) . . . . ? N16 C11 C12 C13 1.4(8) . . . . ? N10 C11 C12 C13 -178.2(5) . . . . ? N16 C15 C14 C13 0.8(10) . . . . ? C12 C13 C14 C15 -1.3(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N10 H10 N1' 0.95(4) 2.35(5) 3.283(6) 168(4) 1_554 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.67 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.309 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.074