# Supplementary Material (ESI) for ChemComm
# This journal is © The Royal Society of Chemistry 1999
# CCDC Number: 182/1379
 
data_w124 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C13 H12 Cu1 N3 S1' 
_chemical_formula_sum 
 'C13 H12 Cu N3 S' 
_chemical_formula_weight          305.86 
 
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' 
 
_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    P2(1)/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                    10.7824(15) 
_cell_length_b                    17.348(2) 
_cell_length_c                    14.0835(18) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  97.405(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      2612.4(6) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        block-like 
_exptl_crystal_colour             red 
_exptl_crystal_size_max           0.10 
_exptl_crystal_size_mid           0.08 
_exptl_crystal_size_min           0.08 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.555 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1248 
_exptl_absorpt_coefficient_mu     1.815 
_exptl_absorpt_correction_type    SADABS
_exptl_absorpt_correction_T_min   0.8774 
_exptl_absorpt_correction_T_max   1.0000 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(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   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             13977 
_diffrn_reflns_av_R_equivalents   0.0886 
_diffrn_reflns_av_sigmaI/netI     0.1921 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -22 
_diffrn_reflns_limit_k_max        17 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          1.87 
_diffrn_reflns_theta_max          27.49 
_reflns_number_total              5941 
_reflns_number_gt                 2215 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_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^)+(0.0553P)^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      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          5941 
_refine_ls_number_parameters      325 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1718 
_refine_ls_R_factor_gt            0.0417 
_refine_ls_wR_factor_ref          0.1158 
_refine_ls_wR_factor_gt           0.0759 
_refine_ls_goodness_of_fit_ref    0.670 
_refine_ls_restrained_S_all       0.670 
_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 
Cu1 Cu -0.39279(6) 0.17679(4) 0.76757(4) 0.0439(2) Uani 1 1 d . . . 
Cu2 Cu 0.11195(6) 0.21779(4) 0.82796(5) 0.0471(2) Uani 1 1 d . . . 
S1 S -0.81154(14) 0.10114(8) 0.78503(11) 0.0552(4) Uani 1 1 d . . . 
S2 S -0.29502(13) 0.20729(9) 0.92025(10) 0.0549(4) Uani 1 1 d . . . 
N1 N -0.5595(4) 0.1341(2) 0.7701(3) 0.0440(11) Uani 1 1 d . . . 
N2 N -0.0463(5) 0.2167(3) 0.8831(3) 0.0530(12) Uani 1 1 d . . . 
N11 N -0.4291(4) 0.2810(2) 0.6891(3) 0.0388(10) Uani 1 1 d . . . 
N21 N -0.2688(4) 0.1182(2) 0.6962(3) 0.0407(11) Uani 1 1 d . . . 
N31 N 0.0651(4) 0.2928(2) 0.7103(3) 0.0457(11) Uani 1 1 d . . . 
N41 N 0.2435(4) 0.2888(2) 0.9070(3) 0.0420(11) Uani 1 1 d . . . 
C1 C -0.6633(5) 0.1214(3) 0.7769(3) 0.0372(13) Uani 1 1 d . . . 
C2 C -0.1481(5) 0.2133(3) 0.8978(3) 0.0383(13) Uani 1 1 d . . . 
C11 C -0.3889(5) 0.3504(3) 0.7193(4) 0.0476(14) Uani 1 1 d . . . 
H11A H -0.3334 0.3535 0.7755 0.057 Uiso 1 1 calc R . . 
C12 C -0.4247(6) 0.4176(3) 0.6724(4) 0.0543(16) Uani 1 1 d . . . 
H12A H -0.3944 0.4645 0.6976 0.065 Uiso 1 1 calc R . . 
C13 C -0.5054(5) 0.4160(3) 0.5881(4) 0.0448(14) Uani 1 1 d . . . 
C14 C -0.5463(5) 0.3442(3) 0.5552(4) 0.0474(15) Uani 1 1 d . . . 
H14A H -0.6000 0.3396 0.4983 0.057 Uiso 1 1 calc R . . 
C15 C -0.5072(5) 0.2798(3) 0.6069(4) 0.0474(14) Uani 1 1 d . . . 
H15A H -0.5369 0.2323 0.5835 0.057 Uiso 1 1 calc R . . 
C16 C -0.5458(6) 0.4886(3) 0.5325(4) 0.0565(16) Uani 1 1 d . . . 
H16A H -0.6267 0.4800 0.4951 0.068 Uiso 1 1 calc R . . 
H16B H -0.5548 0.5303 0.5771 0.068 Uiso 1 1 calc R . . 
C21 C -0.2244(5) 0.1465(3) 0.6192(4) 0.0547(16) Uani 1 1 d . . . 
H21A H -0.2520 0.1951 0.5978 0.066 Uiso 1 1 calc R . . 
C22 C -0.1411(6) 0.1091(3) 0.5692(4) 0.0609(18) Uani 1 1 d . . . 
H22A H -0.1157 0.1319 0.5151 0.073 Uiso 1 1 calc R . . 
C23 C -0.0953(4) 0.0382(3) 0.5992(4) 0.0401(13) Uani 1 1 d . . . 
C24 C -0.1390(5) 0.0085(3) 0.6790(4) 0.0535(16) Uani 1 1 d . . . 
H24A H -0.1117 -0.0395 0.7025 0.064 Uiso 1 1 calc R . . 
C25 C -0.2232(5) 0.0499(3) 0.7243(4) 0.0504(15) Uani 1 1 d . . . 
H25A H -0.2500 0.0283 0.7786 0.060 Uiso 1 1 calc R . . 
C26 C -0.0025(5) -0.0070(3) 0.5508(3) 0.0506(15) Uani 1 1 d . . . 
H26A H 0.0801 0.0030 0.5848 0.061 Uiso 1 1 calc R . . 
H26B H -0.0198 -0.0614 0.5587 0.061 Uiso 1 1 calc R . . 
C31 C 0.1467(6) 0.3142(3) 0.6516(4) 0.0586(17) Uani 1 1 d . . . 
H31A H 0.2252 0.2912 0.6587 0.070 Uiso 1 1 calc R . . 
C32 C 0.1197(6) 0.3690(3) 0.5807(4) 0.0608(17) Uani 1 1 d . . . 
H32A H 0.1801 0.3827 0.5422 0.073 Uiso 1 1 calc R . . 
C33 C 0.0042(6) 0.4033(3) 0.5668(4) 0.0501(15) Uani 1 1 d . . . 
C34 C -0.0787(6) 0.3820(3) 0.6274(4) 0.0610(17) Uani 1 1 d . . . 
H34A H -0.1575 0.4046 0.6223 0.073 Uiso 1 1 calc R . . 
C35 C -0.0453(5) 0.3271(3) 0.6955(4) 0.0563(16) Uani 1 1 d . . . 
H35A H -0.1047 0.3128 0.7345 0.068 Uiso 1 1 calc R . . 
C36 C -0.0286(6) 0.4620(3) 0.4881(4) 0.0638(18) Uani 1 1 d . . . 
H36A H -0.0007 0.4432 0.4295 0.077 Uiso 1 1 calc R . . 
H36B H -0.1188 0.4678 0.4765 0.077 Uiso 1 1 calc R . . 
C41 C 0.3501(5) 0.3081(3) 0.8744(4) 0.0515(15) Uani 1 1 d . . . 
H41A H 0.3751 0.2800 0.8239 0.062 Uiso 1 1 calc R . . 
C42 C 0.4248(5) 0.3683(3) 0.9125(4) 0.0551(16) Uani 1 1 d . . . 
H42A H 0.4976 0.3804 0.8867 0.066 Uiso 1 1 calc R . . 
C43 C 0.3921(5) 0.4105(3) 0.9884(4) 0.0455(14) Uani 1 1 d . . . 
C44 C 0.2843(5) 0.3884(3) 1.0227(4) 0.0442(14) Uani 1 1 d . . . 
H44A H 0.2593 0.4142 1.0749 0.053 Uiso 1 1 calc R . . 
C45 C 0.2127(5) 0.3290(3) 0.9816(4) 0.0449(14) Uani 1 1 d . . . 
H45A H 0.1397 0.3161 1.0065 0.054 Uiso 1 1 calc R . . 
C46 C 0.4679(6) 0.4780(3) 1.0306(4) 0.072(2) Uani 1 1 d . . . 
H46A H 0.4121 0.5122 1.0594 0.086 Uiso 1 1 calc R . . 
H46B H 0.5287 0.4588 1.0819 0.086 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 
Cu1 0.0367(4) 0.0448(4) 0.0520(4) 0.0011(4) 0.0133(3) 0.0053(3) 
Cu2 0.0361(4) 0.0498(5) 0.0559(4) 0.0064(4) 0.0081(3) -0.0018(3) 
S1 0.0370(9) 0.0467(10) 0.0842(11) -0.0067(8) 0.0165(8) -0.0062(7) 
S2 0.0385(9) 0.0845(12) 0.0437(8) -0.0069(8) 0.0125(6) -0.0012(8) 
N1 0.042(3) 0.038(3) 0.054(3) 0.002(2) 0.010(2) 0.000(2) 
N2 0.046(3) 0.063(3) 0.051(3) 0.006(3) 0.012(2) -0.005(3) 
N11 0.042(3) 0.031(3) 0.045(3) -0.001(2) 0.013(2) 0.000(2) 
N21 0.045(3) 0.037(3) 0.042(3) -0.001(2) 0.013(2) 0.007(2) 
N31 0.051(3) 0.043(3) 0.044(3) 0.006(2) 0.009(2) 0.007(2) 
N41 0.039(3) 0.036(3) 0.052(3) 0.000(2) 0.010(2) 0.002(2) 
C1 0.051(4) 0.024(3) 0.036(3) 0.001(2) 0.004(3) 0.003(3) 
C2 0.045(4) 0.038(3) 0.032(3) 0.000(3) 0.004(2) -0.002(3) 
C11 0.054(4) 0.042(4) 0.046(3) -0.002(3) 0.005(3) -0.005(3) 
C12 0.069(4) 0.030(4) 0.063(4) -0.003(3) 0.007(3) -0.009(3) 
C13 0.051(4) 0.040(4) 0.048(4) 0.008(3) 0.021(3) 0.000(3) 
C14 0.054(4) 0.036(4) 0.051(4) 0.004(3) 0.001(3) -0.001(3) 
C15 0.053(4) 0.036(4) 0.052(4) -0.004(3) 0.001(3) -0.005(3) 
C16 0.063(4) 0.039(4) 0.070(4) 0.011(3) 0.017(3) 0.008(3) 
C21 0.065(4) 0.035(3) 0.071(4) 0.007(3) 0.037(3) 0.013(3) 
C22 0.075(5) 0.047(4) 0.071(4) 0.014(3) 0.049(3) 0.016(3) 
C23 0.028(3) 0.044(4) 0.049(3) -0.013(3) 0.010(2) 0.001(3) 
C24 0.063(4) 0.044(4) 0.055(4) 0.003(3) 0.016(3) 0.025(3) 
C25 0.064(4) 0.052(4) 0.037(3) 0.010(3) 0.016(3) 0.014(3) 
C26 0.043(4) 0.046(4) 0.066(4) -0.014(3) 0.020(3) -0.001(3) 
C31 0.067(4) 0.056(4) 0.055(4) 0.012(3) 0.017(3) 0.024(3) 
C32 0.067(5) 0.066(4) 0.053(4) 0.013(3) 0.022(3) 0.010(4) 
C33 0.060(4) 0.041(4) 0.047(4) 0.005(3) 0.000(3) -0.002(3) 
C34 0.051(4) 0.054(4) 0.078(4) 0.018(4) 0.006(3) 0.015(3) 
C35 0.045(4) 0.059(4) 0.067(4) 0.017(4) 0.016(3) 0.007(3) 
C36 0.071(5) 0.056(4) 0.061(4) 0.003(4) -0.005(3) -0.001(3) 
C41 0.045(4) 0.054(4) 0.060(4) -0.013(3) 0.022(3) -0.003(3) 
C42 0.050(4) 0.056(4) 0.063(4) -0.020(3) 0.025(3) -0.023(3) 
C43 0.060(4) 0.038(4) 0.039(3) 0.006(3) 0.007(3) -0.002(3) 
C44 0.050(4) 0.041(4) 0.042(3) 0.000(3) 0.008(3) 0.006(3) 
C45 0.038(3) 0.045(4) 0.053(4) 0.008(3) 0.009(3) 0.002(3) 
C46 0.093(6) 0.052(4) 0.070(5) -0.011(3) 0.010(4) -0.035(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 
Cu1 N1 1.949(5) . ? 
Cu1 N21 2.044(4) . ? 
Cu1 N11 2.128(4) . ? 
Cu1 S2 2.3304(16) . ? 
Cu2 N2 1.964(5) . ? 
Cu2 N41 2.088(4) . ? 
Cu2 N31 2.117(4) . ? 
Cu2 S1 2.2956(16) 1_655 ? 
S1 C1 1.655(6) . ? 
S1 Cu2 2.2956(16) 1_455 ? 
S2 C2 1.658(6) . ? 
N1 C1 1.156(6) . ? 
N2 C2 1.145(6) . ? 
N11 C11 1.331(6) . ? 
N11 C15 1.340(6) . ? 
N21 C25 1.325(6) . ? 
N21 C21 1.334(6) . ? 
N31 C35 1.323(6) . ? 
N31 C31 1.335(7) . ? 
N41 C41 1.334(6) . ? 
N41 C45 1.338(6) . ? 
C11 C12 1.371(7) . ? 
C12 C13 1.379(7) . ? 
C13 C14 1.381(7) . ? 
C13 C16 1.517(7) . ? 
C14 C15 1.370(7) . ? 
C16 C16 1.484(10) 3_466 ? 
C21 C22 1.374(7) . ? 
C22 C23 1.372(7) . ? 
C23 C24 1.374(7) . ? 
C23 C26 1.502(6) . ? 
C24 C25 1.377(7) . ? 
C26 C26 1.460(9) 3_556 ? 
C31 C32 1.383(7) . ? 
C32 C33 1.371(7) . ? 
C33 C34 1.364(7) . ? 
C33 C36 1.513(7) . ? 
C34 C35 1.367(7) . ? 
C36 C36 1.476(10) 3_566 ? 
C41 C42 1.385(7) . ? 
C42 C43 1.379(6) . ? 
C43 C44 1.369(7) . ? 
C43 C46 1.507(7) . ? 
C44 C45 1.371(7) . ? 
C46 C46 1.399(10) 3_667 ? 
 
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 N21 118.93(17) . . ? 
N1 Cu1 N11 102.94(17) . . ? 
N21 Cu1 N11 104.78(16) . . ? 
N1 Cu1 S2 112.19(12) . . ? 
N21 Cu1 S2 108.65(12) . . ? 
N11 Cu1 S2 108.52(13) . . ? 
N2 Cu2 N41 111.12(18) . . ? 
N2 Cu2 N31 100.58(18) . . ? 
N41 Cu2 N31 97.60(16) . . ? 
N2 Cu2 S1 117.09(14) . 1_655 ? 
N41 Cu2 S1 114.68(12) . 1_655 ? 
N31 Cu2 S1 113.18(12) . 1_655 ? 
C1 S1 Cu2 102.37(18) . 1_455 ? 
C2 S2 Cu1 99.66(17) . . ? 
C1 N1 Cu1 168.1(4) . . ? 
C2 N2 Cu2 167.1(4) . . ? 
C11 N11 C15 115.6(5) . . ? 
C11 N11 Cu1 124.9(4) . . ? 
C15 N11 Cu1 119.3(4) . . ? 
C25 N21 C21 114.5(4) . . ? 
C25 N21 Cu1 122.6(3) . . ? 
C21 N21 Cu1 122.9(4) . . ? 
C35 N31 C31 115.4(5) . . ? 
C35 N31 Cu2 121.2(4) . . ? 
C31 N31 Cu2 123.1(4) . . ? 
C41 N41 C45 116.8(4) . . ? 
C41 N41 Cu2 121.3(4) . . ? 
C45 N41 Cu2 120.4(4) . . ? 
N1 C1 S1 178.5(5) . . ? 
N2 C2 S2 179.1(5) . . ? 
N11 C11 C12 123.7(5) . . ? 
C11 C12 C13 120.4(5) . . ? 
C12 C13 C14 116.4(5) . . ? 
C12 C13 C16 122.4(5) . . ? 
C14 C13 C16 121.2(5) . . ? 
C15 C14 C13 119.7(5) . . ? 
N11 C15 C14 124.2(5) . . ? 
C16 C16 C13 111.7(6) 3_466 . ? 
N21 C21 C22 124.7(5) . . ? 
C23 C22 C21 119.9(5) . . ? 
C22 C23 C24 116.1(5) . . ? 
C22 C23 C26 124.3(5) . . ? 
C24 C23 C26 119.6(5) . . ? 
C23 C24 C25 120.0(5) . . ? 
N21 C25 C24 124.7(5) . . ? 
C26 C26 C23 117.9(6) 3_556 . ? 
N31 C31 C32 123.0(6) . . ? 
C33 C32 C31 120.3(5) . . ? 
C34 C33 C32 116.7(5) . . ? 
C34 C33 C36 122.0(6) . . ? 
C32 C33 C36 121.2(5) . . ? 
C33 C34 C35 119.6(6) . . ? 
N31 C35 C34 125.0(5) . . ? 
C36 C36 C33 112.5(6) 3_566 . ? 
N41 C41 C42 122.7(5) . . ? 
C43 C42 C41 120.4(5) . . ? 
C44 C43 C42 116.1(5) . . ? 
C44 C43 C46 121.3(5) . . ? 
C42 C43 C46 122.6(5) . . ? 
C43 C44 C45 121.2(5) . . ? 
N41 C45 C44 122.7(5) . . ? 
C46 C46 C43 117.8(6) 3_667 . ? 
 
_diffrn_measured_fraction_theta_max    0.992 
_diffrn_reflns_theta_full              27.49 
_diffrn_measured_fraction_theta_full   0.992 
_refine_diff_density_max    0.303 
_refine_diff_density_min   -0.289 
_refine_diff_density_rms    0.068