# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 loop_ _publ_author_name _publ_author_address S.Delgado ; Departamento de Quimica Inorganica. Facultad de Ciencias Universidad Autonoma de Madrid, E-28049 Madrid, Spain ; A.Gallego ; Departamento de Quimica Inorganica. Facultad de Ciencias Universidad Autonoma de Madrid, E-28049 Madrid, Spain ; O.Castillo ; Departamento de Quimica Inorganica. Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; F.Zamora ; Departamento de Quimica Inorganica. Facultad de Ciencias Universidad Autonoma de Madrid, E-28049 Madrid, Spain ; _publ_contact_author_name 'Zamora, Felix' _publ_contact_author_email felix.zamora@uam.es _publ_section_title ; Unexpected multiple bond cleavage and rearrangement of organosulfide ligands in the presence of Cu(II) assisted by solvothermal and solvothermal-microwave conditions ; _publ_contact_author ; Salome Delgado. Departamento de Quimica Inorganica. Universidad Aut\'onoma de Madrid, E-28049 Madrid, Spain ; _publ_contact_author_fax '+34-914 974 833' _publ_contact_author_phone '+34-946 974 846' # Attachment '- CIFs_Zamora.cif' data_compound-1 _database_code_depnum_ccdc_archive 'CCDC 781619' #TrackingRef '- CIFs_Zamora.cif' _audit_creation_method SHELXL97 _chemical_name_systematic ; [bis(mu-chlorido)-bis(chlorido)-bis(2-(pyrimidin-2-ylamino) -1,3-thiazole-4-carbaldehyde-k2N:N')dicopper(II)] ; _chemical_formula_moiety 'C16 H12 Cl4 Cu2 N8 O2 S2' _chemical_formula_structural 'C16 H12 Cl4 Cu2 N8 O2 S2' _chemical_formula_sum 'C16 H12 Cl4 Cu2 N8 O2 S2' _chemical_formula_weight 681.34 _chemical_compound_source 'synthesis as described' 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' Cu Cu 0.3201 1.2651 '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' Cl Cl 0.1484 0.1585 '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(1)/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 9.8830(5) _cell_length_b 9.6562(5) _cell_length_c 12.5052(7) _cell_angle_alpha 90.00 _cell_angle_beta 112.968(3) _cell_angle_gamma 90.00 _cell_volume 1098.79(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9975 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 28.72 _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.059 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 2.648 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6921 _exptl_absorpt_correction_T_max 0.8790 _exptl_absorpt_process_details ; Bruker (2008). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _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 26132 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 28.74 _reflns_number_total 2845 _reflns_number_gt 2406 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0250P)^2^+1.7595P] 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 2845 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0248 _refine_ls_wR_factor_ref 0.0651 _refine_ls_wR_factor_gt 0.0600 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 Cu1 Cu 0.49668(3) 0.17789(3) -0.00641(2) 0.01100(8) Uani 1 1 d . . . C1 C 0.1984(2) 0.1364(2) -0.0031(2) 0.0153(4) Uani 1 1 d . . . H1 H 0.2149 0.0427 -0.0177 0.018 Uiso 1 1 calc R . . C2 C 0.0606(3) 0.1753(2) -0.0125(2) 0.0170(4) Uani 1 1 d . . . H2 H -0.0178 0.1106 -0.0325 0.020 Uiso 1 1 calc R . . C3 C 0.0410(3) 0.3132(2) 0.0085(2) 0.0174(5) Uani 1 1 d . . . H3 H -0.0549 0.3444 -0.0030 0.021 Uiso 1 1 calc R . . C4 C 0.2826(2) 0.3553(2) 0.05356(19) 0.0124(4) Uani 1 1 d . . . C5 C 0.5376(2) 0.4355(2) 0.12802(18) 0.0117(4) Uani 1 1 d . . . C6 C 0.7509(2) 0.3373(2) 0.15233(19) 0.0136(4) Uani 1 1 d . . . H6 H 0.8145 0.2652 0.1487 0.016 Uiso 1 1 calc R . . C7 C 0.8014(2) 0.4619(2) 0.20224(19) 0.0149(4) Uani 1 1 d . . . C8 C 0.9511(3) 0.5124(2) 0.2453(2) 0.0192(5) Uani 1 1 d . . . H8 H 1.0266 0.4516 0.2451 0.023 Uiso 1 1 calc R . . S1 S 0.65710(6) 0.56681(5) 0.20007(5) 0.01365(12) Uani 1 1 d . . . Cl1 Cl 0.62402(6) -0.01467(5) 0.14111(4) 0.01379(11) Uani 1 1 d . . . Cl2 Cl 0.65308(6) 0.21941(5) -0.10075(5) 0.01465(11) Uani 1 1 d . . . N1 N 0.59998(19) 0.32359(18) 0.10722(16) 0.0116(3) Uani 1 1 d . . . N2 N 0.3118(2) 0.22727(18) 0.02644(16) 0.0122(4) Uani 1 1 d . . . N3 N 0.1507(2) 0.40308(19) 0.04395(17) 0.0158(4) Uani 1 1 d . . . N4 N 0.3910(2) 0.45375(19) 0.09410(16) 0.0126(4) Uani 1 1 d . . . H4 H 0.3617 0.5388 0.0985 0.015 Uiso 1 1 calc R . . O1 O 0.9840(2) 0.6295(2) 0.28163(17) 0.0272(4) 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 Cu1 0.01062(13) 0.00904(12) 0.01374(14) -0.00189(9) 0.00520(10) -0.00029(9) C1 0.0177(11) 0.0116(9) 0.0182(11) -0.0006(8) 0.0087(9) -0.0022(8) C2 0.0153(11) 0.0159(10) 0.0211(12) -0.0005(9) 0.0084(9) -0.0036(9) C3 0.0130(10) 0.0182(11) 0.0218(12) -0.0008(9) 0.0077(9) 0.0016(8) C4 0.0138(10) 0.0129(9) 0.0109(10) 0.0009(8) 0.0053(8) -0.0002(8) C5 0.0142(10) 0.0121(9) 0.0093(10) 0.0004(8) 0.0051(8) -0.0011(8) C6 0.0123(10) 0.0142(10) 0.0139(10) 0.0016(8) 0.0045(8) 0.0005(8) C7 0.0118(10) 0.0178(10) 0.0135(10) 0.0012(8) 0.0031(8) 0.0011(8) C8 0.0162(11) 0.0239(12) 0.0163(11) -0.0009(9) 0.0051(9) -0.0028(9) S1 0.0129(2) 0.0120(2) 0.0151(3) -0.00235(19) 0.0043(2) -0.00150(19) Cl1 0.0148(2) 0.0119(2) 0.0137(2) -0.00131(18) 0.0045(2) -0.00068(18) Cl2 0.0159(2) 0.0124(2) 0.0187(3) -0.00259(19) 0.0101(2) -0.00124(18) N1 0.0108(8) 0.0109(8) 0.0126(9) 0.0003(7) 0.0040(7) 0.0002(7) N2 0.0130(9) 0.0109(8) 0.0137(9) 0.0000(7) 0.0063(7) -0.0003(7) N3 0.0123(9) 0.0133(9) 0.0228(10) -0.0016(7) 0.0080(8) 0.0013(7) N4 0.0119(9) 0.0103(8) 0.0150(9) -0.0017(7) 0.0046(7) 0.0011(7) O1 0.0220(9) 0.0284(9) 0.0317(10) -0.0073(8) 0.0108(8) -0.0094(8) _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 Cu1 N1 1.9770(18) . ? Cu1 N2 2.0788(18) . ? Cu1 Cl1 2.2751(6) 3_655 ? Cu1 Cl2 2.3163(6) . ? Cu1 Cl1 2.5754(6) . ? C1 N2 1.356(3) . ? C1 C2 1.373(3) . ? C1 H1 0.9500 . ? C2 C3 1.385(3) . ? C2 H2 0.9500 . ? C3 N3 1.323(3) . ? C3 H3 0.9500 . ? C4 N2 1.343(3) . ? C4 N3 1.343(3) . ? C4 N4 1.373(3) . ? C5 N1 1.320(3) . ? C5 N4 1.352(3) . ? C5 S1 1.727(2) . ? C6 C7 1.358(3) . ? C6 N1 1.380(3) . ? C6 H6 0.9500 . ? C7 C8 1.447(3) . ? C7 S1 1.741(2) . ? C8 O1 1.215(3) . ? C8 H8 0.9500 . ? Cl1 Cu1 2.2751(6) 3_655 ? N4 H4 0.8800 . ? 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 Cu1 N2 86.67(7) . . ? N1 Cu1 Cl1 178.43(5) . 3_655 ? N2 Cu1 Cl1 93.32(5) . 3_655 ? N1 Cu1 Cl2 89.02(5) . . ? N2 Cu1 Cl2 150.90(5) . . ? Cl1 Cu1 Cl2 90.23(2) 3_655 . ? N1 Cu1 Cl1 91.61(5) . . ? N2 Cu1 Cl1 104.22(5) . . ? Cl1 Cu1 Cl1 89.92(2) 3_655 . ? Cl2 Cu1 Cl1 104.66(2) . . ? N2 C1 C2 122.2(2) . . ? N2 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C1 C2 C3 117.0(2) . . ? C1 C2 H2 121.5 . . ? C3 C2 H2 121.5 . . ? N3 C3 C2 122.5(2) . . ? N3 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? N2 C4 N3 126.2(2) . . ? N2 C4 N4 121.14(19) . . ? N3 C4 N4 112.69(19) . . ? N1 C5 N4 124.8(2) . . ? N1 C5 S1 115.25(16) . . ? N4 C5 S1 119.93(16) . . ? C7 C6 N1 114.68(19) . . ? C7 C6 H6 122.7 . . ? N1 C6 H6 122.7 . . ? C6 C7 C8 127.5(2) . . ? C6 C7 S1 110.88(16) . . ? C8 C7 S1 121.48(18) . . ? O1 C8 C7 122.5(2) . . ? O1 C8 H8 118.7 . . ? C7 C8 H8 118.7 . . ? C5 S1 C7 88.32(11) . . ? Cu1 Cl1 Cu1 90.08(2) 3_655 . ? C5 N1 C6 110.79(18) . . ? C5 N1 Cu1 125.06(15) . . ? C6 N1 Cu1 122.32(14) . . ? C4 N2 C1 115.38(18) . . ? C4 N2 Cu1 123.58(14) . . ? C1 N2 Cu1 119.63(14) . . ? C3 N3 C4 116.40(19) . . ? C5 N4 C4 127.72(18) . . ? C5 N4 H4 116.1 . . ? C4 N4 H4 116.1 . . ? 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 N2 C1 C2 C3 0.6(3) . . . . ? C1 C2 C3 N3 -4.6(4) . . . . ? N1 C6 C7 C8 -172.8(2) . . . . ? N1 C6 C7 S1 2.8(3) . . . . ? C6 C7 C8 O1 174.9(2) . . . . ? S1 C7 C8 O1 -0.2(3) . . . . ? N1 C5 S1 C7 -0.18(17) . . . . ? N4 C5 S1 C7 -178.14(18) . . . . ? C6 C7 S1 C5 -1.45(18) . . . . ? C8 C7 S1 C5 174.4(2) . . . . ? N1 Cu1 Cl1 Cu1 -179.62(5) . . . 3_655 ? N2 Cu1 Cl1 Cu1 93.40(5) . . . 3_655 ? Cl1 Cu1 Cl1 Cu1 0.0 3_655 . . 3_655 ? Cl2 Cu1 Cl1 Cu1 -90.22(2) . . . 3_655 ? N4 C5 N1 C6 179.6(2) . . . . ? S1 C5 N1 C6 1.7(2) . . . . ? N4 C5 N1 Cu1 14.8(3) . . . . ? S1 C5 N1 Cu1 -163.09(11) . . . . ? C7 C6 N1 C5 -2.9(3) . . . . ? C7 C6 N1 Cu1 162.39(16) . . . . ? N2 Cu1 N1 C5 -29.94(18) . . . . ? Cl2 Cu1 N1 C5 121.27(17) . . . . ? Cl1 Cu1 N1 C5 -134.09(17) . . . . ? N2 Cu1 N1 C6 166.90(17) . . . . ? Cl2 Cu1 N1 C6 -41.90(16) . . . . ? Cl1 Cu1 N1 C6 62.75(16) . . . . ? N3 C4 N2 C1 -6.3(3) . . . . ? N4 C4 N2 C1 174.6(2) . . . . ? N3 C4 N2 Cu1 159.98(17) . . . . ? N4 C4 N2 Cu1 -19.1(3) . . . . ? C2 C1 N2 C4 4.4(3) . . . . ? C2 C1 N2 Cu1 -162.50(18) . . . . ? N1 Cu1 N2 C4 32.29(17) . . . . ? Cl1 Cu1 N2 C4 -146.13(17) 3_655 . . . ? Cl2 Cu1 N2 C4 -49.7(2) . . . . ? Cl1 Cu1 N2 C4 123.11(16) . . . . ? N1 Cu1 N2 C1 -161.92(17) . . . . ? Cl1 Cu1 N2 C1 19.65(17) 3_655 . . . ? Cl2 Cu1 N2 C1 116.11(16) . . . . ? Cl1 Cu1 N2 C1 -71.11(17) . . . . ? C2 C3 N3 C4 3.1(3) . . . . ? N2 C4 N3 C3 2.7(3) . . . . ? N4 C4 N3 C3 -178.1(2) . . . . ? N1 C5 N4 C4 13.7(3) . . . . ? S1 C5 N4 C4 -168.55(17) . . . . ? N2 C4 N4 C5 -10.3(3) . . . . ? N3 C4 N4 C5 170.5(2) . . . . ? 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 N4 H4 Cl2 0.88 2.34 3.1915(19) 162.9 3_665 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.74 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.577 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.090 _chemical_name_common ; (bis(mu-chlorido)-bis(chlorido)-bis(2-(pyrimidin-2-ylamino) - 1,3-thiazole-4-carbaldehyde-k2N:N')dicopper(ii)) ; #===END data_compound-2 _database_code_depnum_ccdc_archive 'CCDC 781620' _audit_creation_method SHELXL97 _chemical_name_systematic ; poly-[mu-chlorido-(mu-bis(2-pyrimidyl-disulfide-k2N:N')copper(I)]-methanol (1/1) ; _chemical_formula_moiety 'C16 H12 Cl4 Cu2 N8 S5.80' _chemical_formula_structural 'C16 H12 Cl4 Cu2 N8 S5.80' _chemical_formula_sum 'C16 H12 Cl4 Cu2 N8 S5.80' _chemical_formula_weight 771.11 _chemical_compound_source 'synthesis as described' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 11.9670(6) _cell_length_b 6.8657(4) _cell_length_c 16.9169(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.541(3) _cell_angle_gamma 90.00 _cell_volume 1301.55(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 20691 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 29.72 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.984 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 765.5 _exptl_absorpt_coefficient_mu 2.553 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.170.32 (release 06.06.2003 CrysAlis170 VC++) (compiled Jun 6 2003,13:53:32) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. ; _exptl_absorpt_correction_T_min 0.738 _exptl_absorpt_correction_T_max 0.834 _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method \w _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 20691 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 29.72 _reflns_number_total 3681 _reflns_number_gt 3144 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Sir92 (Altamore et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0345P)^2^+5.4377P] 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 3681 _refine_ls_number_parameters 171 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.170 _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 Cu1 Cu 0.15932(4) -0.04280(6) 0.06289(3) 0.01568(12) Uani 1 1 d . . . Cl1 Cl -0.01112(8) -0.18839(13) 0.06373(5) 0.01706(18) Uani 1 1 d . . . Cl2 Cl 0.19155(8) -0.25764(14) -0.02888(6) 0.0227(2) Uani 1 1 d . A . N1 N 0.3159(4) 0.0884(7) 0.0685(4) 0.018(2) Uiso 0.898(2) 1 d PD A -1 N2 N 0.5258(3) 0.0836(6) 0.1026(3) 0.0232(9) Uiso 0.898(2) 1 d PD A -1 N3 N 0.1548(3) 0.1366(6) 0.1595(2) 0.0164(6) Uiso 0.898(2) 1 d PDU A -1 N4 N 0.1955(4) 0.2028(6) 0.3058(2) 0.0226(8) Uiso 0.898(2) 1 d PD A -1 C1 C 0.4265(4) 0.0220(6) 0.1113(3) 0.0189(8) Uiso 0.898(2) 1 d PD A -1 C2 C 0.5152(5) 0.2231(9) 0.0450(3) 0.0258(12) Uiso 0.898(2) 1 d PD A -1 H2 H 0.5833 0.2667 0.0358 0.031 Uiso 0.898(2) 1 calc PR A -1 C3 C 0.4077(4) 0.3029(8) -0.0004(3) 0.0255(9) Uiso 0.898(2) 1 d PD A -1 H3 H 0.4012 0.4002 -0.0400 0.031 Uiso 0.898(2) 1 calc PR A -1 C4 C 0.3085(4) 0.2342(6) 0.0144(3) 0.0212(9) Uiso 0.898(2) 1 d PDU A -1 H4 H 0.2346 0.2906 -0.0140 0.025 Uiso 0.898(2) 1 calc PR A -1 C5 C 0.1992(5) 0.0932(6) 0.2423(3) 0.0182(12) Uiso 0.898(2) 1 d PD A -1 C6 C 0.1393(4) 0.3714(6) 0.2859(3) 0.0209(8) Uiso 0.898(2) 1 d PDU A -1 H6 H 0.1344 0.4517 0.3289 0.025 Uiso 0.898(2) 1 calc PR A -1 C7 C 0.0881(4) 0.4312(6) 0.2038(3) 0.0189(9) Uiso 0.898(2) 1 d PD A -1 H7 H 0.0489 0.5502 0.1905 0.023 Uiso 0.898(2) 1 calc PR A -1 C8 C 0.0966(4) 0.3090(7) 0.1411(4) 0.0166(11) Uiso 0.898(2) 1 d PD A -1 H8 H 0.0615 0.3463 0.0850 0.020 Uiso 0.898(2) 1 calc PR A -1 S1 S 0.45942(10) -0.17358(18) 0.18336(8) 0.0265(3) Uani 0.898(2) 1 d P A -1 S2 S 0.29923(9) -0.26903(15) 0.18556(7) 0.0194(2) Uani 0.898(2) 1 d P A -1 S3 S 0.27145(11) -0.12997(16) 0.28327(7) 0.0238(3) Uani 0.898(2) 1 d P A -1 N1A N 0.3234(9) 0.095(3) 0.0769(17) 0.013(18) Uiso 0.102(2) 1 d PD A -2 N2A N 0.5352(8) 0.087(3) 0.1262(15) 0.024(10) Uiso 0.102(2) 1 d PD A -2 N3A N 0.1428(9) 0.148(4) 0.1566(11) 0.0164(11) Uiso 0.102(2) 1 d PDU A -2 N4A N 0.2361(10) 0.182(3) 0.3062(11) 0.016(6) Uiso 0.102(2) 1 d PD A -2 C1A C 0.4311(11) 0.0453(17) 0.1327(12) 0.040(15) Uiso 0.102(2) 1 d PD A -2 C2A C 0.5330(17) 0.187(3) 0.0577(17) 0.012(8) Uiso 0.102(2) 1 d PD A -2 H2A H 0.6048 0.2184 0.0511 0.015 Uiso 0.102(2) 1 calc PR A -2 C3A C 0.429(2) 0.244(3) -0.0025(13) 0.017(7) Uiso 0.102(2) 1 d PD A -2 H3A H 0.4285 0.3132 -0.0498 0.020 Uiso 0.102(2) 1 calc PR A -2 C4A C 0.3241(16) 0.195(4) 0.0092(16) 0.0211(13) Uiso 0.102(2) 1 d PDU A -2 H4A H 0.2518 0.2319 -0.0312 0.025 Uiso 0.102(2) 1 calc PR A -2 C5A C 0.2131(4) 0.088(3) 0.2339(12) 0.020(14) Uiso 0.102(2) 1 d PD A -2 C6A C 0.1848(17) 0.354(3) 0.3025(15) 0.0205(13) Uiso 0.102(2) 1 d PDU A -2 H6A H 0.1990 0.4245 0.3521 0.025 Uiso 0.102(2) 1 calc PR A -2 C7A C 0.1113(19) 0.432(3) 0.2277(19) 0.029(12) Uiso 0.102(2) 1 d PD A -2 H7A H 0.0757 0.5527 0.2259 0.035 Uiso 0.102(2) 1 calc PR A -2 C8A C 0.0916(15) 0.324(4) 0.1549(14) 0.030(17) Uiso 0.102(2) 1 d PD A -2 H8A H 0.0419 0.3744 0.1035 0.037 Uiso 0.102(2) 1 calc PR A -2 S1A S 0.4379(9) -0.0851(14) 0.2225(7) 0.025(2) Uani 0.102(2) 1 d PD A -2 S2A S 0.2737(8) -0.1489(14) 0.2242(6) 0.022(2) Uani 0.102(2) 1 d PD A -2 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 Cu1 0.0153(2) 0.0177(2) 0.0147(2) -0.00229(16) 0.00604(16) -0.00325(16) Cl1 0.0163(4) 0.0190(4) 0.0159(4) 0.0022(3) 0.0056(3) -0.0032(3) Cl2 0.0195(4) 0.0244(4) 0.0259(4) -0.0081(4) 0.0102(4) -0.0031(3) S1 0.0175(5) 0.0283(6) 0.0321(6) 0.0066(5) 0.0068(5) 0.0027(4) S2 0.0200(5) 0.0171(5) 0.0214(5) 0.0005(4) 0.0075(4) 0.0007(4) S3 0.0324(6) 0.0217(5) 0.0167(5) 0.0047(4) 0.0079(4) 0.0072(4) S1A 0.021(5) 0.019(4) 0.026(5) 0.012(4) -0.001(4) 0.001(3) S2A 0.016(4) 0.020(4) 0.028(5) 0.005(4) 0.005(4) -0.002(3) _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 Cu1 N1 2.050(4) . ? Cu1 N3 2.062(4) . ? Cu1 N1A 2.115(12) . ? Cu1 N3A 2.12(2) . ? Cu1 Cl2 2.2705(10) . ? Cu1 Cl1 2.2760(9) . ? Cu1 S2 2.6616(11) . ? Cu1 S2A 2.689(10) . ? Cu1 Cl1 2.7545(10) 3 ? Cl1 Cu1 2.7545(10) 3 ? N1 C4 1.339(5) . ? N1 C1 1.346(6) . ? N2 C1 1.317(5) . ? N2 C2 1.341(7) . ? N3 C5 1.347(5) . ? N3 C8 1.353(5) . ? N4 C6 1.321(6) . ? N4 C5 1.325(6) . ? C1 S1 1.763(4) . ? C2 C3 1.361(8) . ? C3 C4 1.378(6) . ? C5 S3 1.776(5) . ? C6 C7 1.371(7) . ? C7 C8 1.383(7) . ? S1 S2 2.0385(15) . ? S2 S3 2.0348(15) . ? N1A C4A 1.339(7) . ? N1A C1A 1.345(7) . ? N2A C1A 1.319(8) . ? N2A C2A 1.340(8) . ? N3A C5A 1.347(6) . ? N3A C8A 1.353(7) . ? N4A C6A 1.321(7) . ? N4A C5A 1.325(7) . ? C1A S1A 1.74(2) . ? C2A C3A 1.361(9) . ? C3A C4A 1.378(7) . ? C5A S2A 1.81(2) . ? C6A C7A 1.370(8) . ? C7A C8A 1.383(8) . ? S1A S2A 2.023(14) . ? 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 Cu1 N3 88.8(2) . . ? N1 Cu1 N1A 3.6(8) . . ? N3 Cu1 N1A 85.8(7) . . ? N1 Cu1 N3A 91.0(5) . . ? N3 Cu1 N3A 4.0(3) . . ? N1A Cu1 N3A 88.1(8) . . ? N1 Cu1 Cl2 86.87(16) . . ? N3 Cu1 Cl2 171.07(10) . . ? N1A Cu1 Cl2 89.6(7) . . ? N3A Cu1 Cl2 175.0(4) . . ? N1 Cu1 Cl1 177.17(17) . . ? N3 Cu1 Cl1 89.12(11) . . ? N1A Cu1 Cl1 173.6(7) . . ? N3A Cu1 Cl1 87.0(5) . . ? Cl2 Cu1 Cl1 94.97(4) . . ? N1 Cu1 S2 84.58(13) . . ? N3 Cu1 S2 85.12(10) . . ? N1A Cu1 S2 82.4(6) . . ? N3A Cu1 S2 88.6(5) . . ? Cl2 Cu1 S2 86.71(4) . . ? Cl1 Cu1 S2 93.37(3) . . ? N1 Cu1 S2A 86.6(2) . . ? N3 Cu1 S2A 60.2(2) . . ? N1A Cu1 S2A 83.4(7) . . ? N3A Cu1 S2A 63.6(6) . . ? Cl2 Cu1 S2A 111.7(2) . . ? Cl1 Cu1 S2A 90.73(19) . . ? S2 Cu1 S2A 25.0(2) . . ? N1 Cu1 Cl1 96.40(13) . 3 ? N3 Cu1 Cl1 94.78(10) . 3 ? N1A Cu1 Cl1 98.6(6) . 3 ? N3A Cu1 Cl1 91.3(5) . 3 ? Cl2 Cu1 Cl1 93.44(3) . 3 ? Cl1 Cu1 Cl1 85.65(3) . 3 ? S2 Cu1 Cl1 179.01(3) . 3 ? S2A Cu1 Cl1 154.8(2) . 3 ? Cu1 Cl1 Cu1 94.35(3) . 3 ? C4 N1 C1 115.9(4) . . ? C4 N1 Cu1 117.2(4) . . ? C1 N1 Cu1 125.9(3) . . ? C1 N2 C2 116.8(4) . . ? C5 N3 C8 114.6(4) . . ? C5 N3 Cu1 125.6(3) . . ? C8 N3 Cu1 119.7(3) . . ? C6 N4 C5 116.8(4) . . ? N2 C1 N1 126.0(4) . . ? N2 C1 S1 109.3(3) . . ? N1 C1 S1 124.6(3) . . ? N2 C2 C3 121.8(4) . . ? C2 C3 C4 117.6(4) . . ? N1 C4 C3 121.8(4) . . ? N4 C5 N3 127.2(4) . . ? N4 C5 S3 108.9(3) . . ? N3 C5 S3 123.8(4) . . ? N4 C6 C7 121.8(4) . . ? C6 C7 C8 118.0(4) . . ? N3 C8 C7 121.7(4) . . ? C1 S1 S2 105.92(14) . . ? S3 S2 S1 106.66(7) . . ? S3 S2 Cu1 97.02(5) . . ? S1 S2 Cu1 97.84(5) . . ? C5 S3 S2 106.5(2) . . ? C4A N1A C1A 115.9(5) . . ? C4A N1A Cu1 114.6(12) . . ? C1A N1A Cu1 126.1(10) . . ? C1A N2A C2A 116.7(5) . . ? C5A N3A C8A 114.6(5) . . ? C5A N3A Cu1 110.4(11) . . ? C8A N3A Cu1 134.3(12) . . ? C6A N4A C5A 116.8(5) . . ? N2A C1A N1A 126.0(5) . . ? N2A C1A S1A 115.3(11) . . ? N1A C1A S1A 118.7(10) . . ? N2A C2A C3A 121.9(5) . . ? C2A C3A C4A 117.6(5) . . ? N1A C4A C3A 121.8(5) . . ? N4A C5A N3A 127.2(5) . . ? N4A C5A S2A 124.2(11) . . ? N3A C5A S2A 108.6(12) . . ? N4A C6A C7A 121.8(5) . . ? C6A C7A C8A 118.0(5) . . ? N3A C8A C7A 121.6(5) . . ? C1A S1A S2A 112.1(7) . . ? C5A S2A S1A 103.2(5) . . ? C5A S2A Cu1 76.8(7) . . ? S1A S2A Cu1 94.5(4) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 29.72 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.820 _refine_diff_density_min -0.539 _refine_diff_density_rms 0.132 #===END data_compound-3 _database_code_depnum_ccdc_archive 'CCDC 781621' _audit_creation_method SHELXL97 _chemical_name_systematic ; 2-(pyrimidin-2-ylamino)-1,3-thiazole-4-carbaldehyde ; _chemical_formula_moiety 'C8 H6 N4 O S' _chemical_formula_structural 'C8 H6 N4 O S' _chemical_formula_sum 'C8 H6 N4 O S' _chemical_formula_weight 206.23 _chemical_compound_source 'synthesis as described' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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(1)/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 5.4675(4) _cell_length_b 21.7393(16) _cell_length_c 8.3532(5) _cell_angle_alpha 90.00 _cell_angle_beta 120.377(4) _cell_angle_gamma 90.00 _cell_volume 856.56(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10249 _cell_measurement_theta_min 4.07 _cell_measurement_theta_max 71.06 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 3.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6921 _exptl_absorpt_correction_T_max 0.8790 _exptl_absorpt_process_details ; Bruker (2008). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _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 10249 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 71.06 _reflns_number_total 1612 _reflns_number_gt 1554 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0468P)^2^+0.4388P] 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 1612 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0852 _refine_ls_wR_factor_gt 0.0840 _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 S1 S 0.25580(7) -0.089332(16) 0.78828(5) 0.01558(15) Uani 1 1 d . . . C1 C 0.3819(3) -0.15233(7) 0.7242(2) 0.0172(3) Uani 1 1 d . . . C2 C 0.4905(3) -0.13407(7) 0.6160(2) 0.0168(3) Uani 1 1 d . . . H2 H 0.5679 -0.1625 0.5672 0.020 Uiso 1 1 calc R . . C3 C 0.3643(3) -0.04329(7) 0.66651(19) 0.0140(3) Uani 1 1 d . . . C4 C 0.3737(3) -0.21345(7) 0.7869(2) 0.0215(3) Uani 1 1 d . . . H4 H 0.4420 -0.2462 0.7448 0.026 Uiso 1 1 calc R . . C5 C 0.2233(3) 0.05661(7) 0.72893(19) 0.0145(3) Uani 1 1 d . . . C6 C 0.0059(3) 0.06955(8) 0.8961(2) 0.0186(3) Uani 1 1 d . . . H6 H -0.0707 0.0534 0.9672 0.022 Uiso 1 1 calc R . . C7 C -0.0030(3) 0.13210(8) 0.8690(2) 0.0199(3) Uani 1 1 d . . . H7 H -0.0860 0.1591 0.9175 0.024 Uiso 1 1 calc R . . C8 C 0.1156(3) 0.15363(7) 0.7668(2) 0.0187(3) Uani 1 1 d . . . H8 H 0.1138 0.1967 0.7464 0.022 Uiso 1 1 calc R . . N1 N 0.4809(3) -0.07271(6) 0.58270(17) 0.0158(3) Uani 1 1 d . . . N2 N 0.3372(3) 0.01878(6) 0.65118(17) 0.0152(3) Uani 1 1 d . . . H2A H 0.3993 0.0368 0.5842 0.018 Uiso 1 1 calc R . . N3 N 0.1177(2) 0.03052(6) 0.82695(16) 0.0140(3) Uani 1 1 d . . . N4 N 0.2319(2) 0.11673(6) 0.69606(17) 0.0166(3) Uani 1 1 d . . . O1 O 0.2847(3) -0.22611(6) 0.89074(17) 0.0290(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 S1 0.0197(2) 0.0138(2) 0.0182(2) -0.00020(12) 0.01330(17) -0.00127(12) C1 0.0186(7) 0.0153(8) 0.0175(7) -0.0009(6) 0.0090(6) -0.0012(5) C2 0.0184(7) 0.0145(8) 0.0188(7) -0.0007(5) 0.0102(6) 0.0000(5) C3 0.0124(6) 0.0157(8) 0.0143(7) -0.0004(5) 0.0071(6) -0.0015(5) C4 0.0286(8) 0.0152(8) 0.0229(8) -0.0021(6) 0.0146(7) -0.0027(6) C5 0.0131(6) 0.0159(8) 0.0137(7) -0.0004(5) 0.0062(6) 0.0001(5) C6 0.0182(7) 0.0217(9) 0.0193(7) -0.0012(6) 0.0120(6) -0.0005(6) C7 0.0194(7) 0.0209(8) 0.0207(8) -0.0027(6) 0.0111(6) 0.0014(6) C8 0.0189(7) 0.0148(8) 0.0217(8) -0.0010(6) 0.0097(6) 0.0006(5) N1 0.0175(6) 0.0147(7) 0.0187(6) -0.0003(5) 0.0117(5) -0.0004(5) N2 0.0190(6) 0.0130(7) 0.0192(6) 0.0015(5) 0.0137(5) -0.0007(4) N3 0.0148(6) 0.0144(6) 0.0158(6) -0.0004(4) 0.0099(5) -0.0001(5) N4 0.0172(6) 0.0158(7) 0.0184(6) 0.0004(5) 0.0102(5) -0.0002(5) O1 0.0459(7) 0.0196(6) 0.0312(7) 0.0000(5) 0.0266(6) -0.0071(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 S1 C3 1.7315(14) . ? S1 C1 1.7352(15) . ? C1 C2 1.368(2) . ? C1 C4 1.437(2) . ? C2 N1 1.358(2) . ? C2 H2 0.9500 . ? C3 N1 1.3256(19) . ? C3 N2 1.356(2) . ? C4 O1 1.221(2) . ? C4 H4 0.9500 . ? C5 N4 1.341(2) . ? C5 N3 1.3428(19) . ? C5 N2 1.3766(19) . ? C6 N3 1.3361(19) . ? C6 C7 1.375(2) . ? C6 H6 0.9500 . ? C7 C8 1.388(2) . ? C7 H7 0.9500 . ? C8 N4 1.333(2) . ? C8 H8 0.9500 . ? N2 H2A 0.8800 . ? 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 C3 S1 C1 88.14(7) . . ? C2 C1 C4 127.83(14) . . ? C2 C1 S1 110.36(11) . . ? C4 C1 S1 121.79(12) . . ? N1 C2 C1 115.82(13) . . ? N1 C2 H2 122.1 . . ? C1 C2 H2 122.1 . . ? N1 C3 N2 119.26(13) . . ? N1 C3 S1 115.50(11) . . ? N2 C3 S1 125.25(11) . . ? O1 C4 C1 124.34(15) . . ? O1 C4 H4 117.8 . . ? C1 C4 H4 117.8 . . ? N4 C5 N3 127.36(13) . . ? N4 C5 N2 114.49(13) . . ? N3 C5 N2 118.15(13) . . ? N3 C6 C7 122.85(14) . . ? N3 C6 H6 118.6 . . ? C7 C6 H6 118.6 . . ? C6 C7 C8 116.49(14) . . ? C6 C7 H7 121.8 . . ? C8 C7 H7 121.8 . . ? N4 C8 C7 123.05(14) . . ? N4 C8 H8 118.5 . . ? C7 C8 H8 118.5 . . ? C3 N1 C2 110.18(12) . . ? C3 N2 C5 127.12(12) . . ? C3 N2 H2A 116.4 . . ? C5 N2 H2A 116.4 . . ? C6 N3 C5 115.29(13) . . ? C8 N4 C5 114.94(12) . . ? 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 C3 S1 C1 C2 -0.75(11) . . . . ? C3 S1 C1 C4 177.43(13) . . . . ? C4 C1 C2 N1 -177.54(14) . . . . ? S1 C1 C2 N1 0.50(17) . . . . ? C1 S1 C3 N1 0.92(11) . . . . ? C1 S1 C3 N2 -179.40(13) . . . . ? C2 C1 C4 O1 176.46(16) . . . . ? S1 C1 C4 O1 -1.4(2) . . . . ? N3 C6 C7 C8 -1.0(2) . . . . ? C6 C7 C8 N4 0.4(2) . . . . ? N2 C3 N1 C2 179.50(12) . . . . ? S1 C3 N1 C2 -0.80(15) . . . . ? C1 C2 N1 C3 0.17(18) . . . . ? N1 C3 N2 C5 -179.70(13) . . . . ? S1 C3 N2 C5 0.6(2) . . . . ? N4 C5 N2 C3 177.86(13) . . . . ? N3 C5 N2 C3 -2.2(2) . . . . ? C7 C6 N3 C5 0.3(2) . . . . ? N4 C5 N3 C6 1.0(2) . . . . ? N2 C5 N3 C6 -178.90(12) . . . . ? C7 C8 N4 C5 0.7(2) . . . . ? N3 C5 N4 C8 -1.6(2) . . . . ? N2 C5 N4 C8 178.38(12) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 71.06 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.403 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.062