# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Guo-Cong Guo' _publ_contact_author_email GCGUO@FJIRSM.AC.CN _publ_section_title ; Molecular Design of Luminescent Halogeno-thiocyano-d10 Metal Complexes with in situ Formation of Thiocyanate Ligand ; loop_ _publ_author_name 'Guo-Cong Guo' 'Kun-Lin Huang' 'Guo-Ming Liang' 'Xi Liu' ; Ming-Sheng Wang ; # Attachment 'Complexes.CIF' # Authors: Xi Liu, Kun-Lin Huang, Guo-Ming Liang, Ming-Sheng Wang, Guo-Cong Guo # Title: Molecular Design of Luminescent Halogeno-thiocyano-d10 Metal # Complexes with Thiocyanate Ligand in situ Formation # Pre-publication: CrystEngComm # Name of author for correspondence: Xi Liu # Address: College of Chemistry, Chongqing Normal University, # Chongqing 400047, People's Republic of China # E-mail: 'xliu@cqnu.edu.cn' # Fax: '8602365362770' # Phone: '8602365362777' data_comp1 _database_code_depnum_ccdc_archive 'CCDC 714859' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H12 Br Cu N2 S' _chemical_formula_weight 275.68 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' Cu Cu 0.3201 1.2651 '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' 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(1)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 5.898(4) _cell_length_b 7.371(5) _cell_length_c 11.310(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.064(2) _cell_angle_gamma 90.00 _cell_volume 489.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1012 _cell_measurement_theta_min 3.3070 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.0400 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.872 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 6.469 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5993 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating-anode generator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3217 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 25.03 _reflns_number_total 935 _reflns_number_gt 806 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2002)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2002)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2002)' _computing_structure_solution 'Siemens SHELXTL^TM^ 5' _computing_structure_refinement 'Siemens SHELXTL^TM^ 5' _computing_molecular_graphics 'Siemens SHELXTL^TM^ 5' _computing_publication_material 'Siemens SHELXTL^TM^ 5' _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^)+(0.0420P)^2^+0.0900P] 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 935 _refine_ls_number_parameters 58 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0730 _refine_ls_wR_factor_gt 0.0693 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.94402(9) 0.2500 0.65190(5) 0.0453(2) Uani 1 2 d S . . Br1 Br 1.08497(8) 0.2500 0.85625(4) 0.0467(2) Uani 1 2 d S . . S1 S 0.1706(2) 0.2500 0.50641(12) 0.0733(5) Uani 1 2 d S . . N1 N 0.6225(6) 0.2500 0.6062(4) 0.0500(11) Uani 1 2 d S . . N11 N 0.5402(6) 0.2500 0.1877(3) 0.0324(8) Uani 1 2 d S . . C1 C 0.4348(8) 0.2500 0.5683(4) 0.0417(11) Uani 1 2 d S . . C11 C 0.3942(6) 0.0860(5) 0.1886(4) 0.0582(10) Uani 1 1 d . . . H11A H 0.2848 0.0863 0.1194 0.087 Uiso 1 1 calc R . . H11B H 0.3158 0.0864 0.2588 0.087 Uiso 1 1 calc R . . H11D H 0.4875 -0.0206 0.1881 0.087 Uiso 1 1 calc R . . C12 C 0.6602(9) 0.2500 0.0783(4) 0.0506(13) Uani 1 2 d S . . H12C H 0.7528 0.3569 0.0771 0.076 Uiso 0.50 1 calc PR . . H12D H 0.5500 0.2488 0.0095 0.076 Uiso 1 2 calc SR . . H12A H 0.7551 0.1443 0.0778 0.076 Uiso 0.50 1 calc PR . . C13 C 0.7122(10) 0.2500 0.2934(4) 0.0688(17) Uani 1 2 d S . . H13D H 0.8047 0.3571 0.2926 0.103 Uiso 0.50 1 calc PR . . H13B H 0.8071 0.1444 0.2916 0.103 Uiso 0.50 1 calc PR . . H13A H 0.6362 0.2485 0.3644 0.103 Uiso 1 2 calc SR . . 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 0.0243(3) 0.0607(4) 0.0508(4) 0.000 0.0040(2) 0.000 Br1 0.0390(3) 0.0565(3) 0.0435(3) 0.000 -0.0004(2) 0.000 S1 0.0247(6) 0.1563(16) 0.0382(7) 0.000 0.0009(5) 0.000 N1 0.025(2) 0.081(3) 0.045(2) 0.000 0.0074(17) 0.000 N11 0.0302(19) 0.0334(19) 0.0332(19) 0.000 0.0019(15) 0.000 C1 0.032(3) 0.060(3) 0.036(2) 0.000 0.013(2) 0.000 C11 0.055(2) 0.045(2) 0.077(3) 0.004(2) 0.020(2) -0.0113(18) C12 0.052(3) 0.060(3) 0.041(3) 0.000 0.012(2) 0.000 C13 0.063(4) 0.099(5) 0.040(3) 0.000 -0.014(3) 0.000 _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 1.912(4) . ? Cu1 S1 2.2266(17) 1_655 ? Cu1 Br1 2.3720(15) . ? S1 C1 1.640(5) . ? S1 Cu1 2.2266(17) 1_455 ? N1 C1 1.144(6) . ? N11 C13 1.484(6) . ? N11 C11 1.485(4) . ? N11 C11 1.485(4) 4_565 ? N11 C12 1.489(6) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11D 0.9600 . ? C12 H12C 0.9600 . ? C12 H12D 0.9600 . ? C12 H12A 0.9600 . ? C13 H13D 0.9600 . ? C13 H13B 0.9600 . ? C13 H13A 0.9600 . ? 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 S1 117.12(13) . 1_655 ? N1 Cu1 Br1 119.91(12) . . ? S1 Cu1 Br1 122.97(6) 1_655 . ? C1 S1 Cu1 107.60(17) . 1_455 ? C1 N1 Cu1 173.7(4) . . ? C13 N11 C11 110.0(3) . . ? C13 N11 C11 110.0(3) . 4_565 ? C11 N11 C11 109.0(4) . 4_565 ? C13 N11 C12 108.9(4) . . ? C11 N11 C12 109.4(2) . . ? C11 N11 C12 109.4(2) 4_565 . ? N1 C1 S1 176.8(4) . . ? N11 C11 H11A 109.5 . . ? N11 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N11 C11 H11D 109.5 . . ? H11A C11 H11D 109.5 . . ? H11B C11 H11D 109.5 . . ? N11 C12 H12C 109.5 . . ? N11 C12 H12D 109.5 . . ? H12C C12 H12D 109.5 . . ? N11 C12 H12A 109.5 . . ? H12C C12 H12A 109.5 . . ? H12D C12 H12A 109.5 . . ? N11 C13 H13D 109.5 . . ? N11 C13 H13B 109.5 . . ? H13D C13 H13B 109.5 . . ? N11 C13 H13A 109.5 . . ? H13D C13 H13A 109.5 . . ? H13B C13 H13A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.373 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.069 #===END data_Comp2 _database_code_depnum_ccdc_archive 'CCDC 714860' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H12 Cu I N2 S' _chemical_formula_weight 322.67 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' I I -0.4742 1.8119 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.931(6) _cell_length_b 7.710(7) _cell_length_c 11.488(10) _cell_angle_alpha 101.668(13) _cell_angle_beta 95.652(18) _cell_angle_gamma 90.59(2) _cell_volume 511.7(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1464 _cell_measurement_theta_min 3.4529 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Prism _exptl_crystal_colour Orange _exptl_crystal_size_max 0.5000 _exptl_crystal_size_mid 0.0800 _exptl_crystal_size_min 0.0800 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.094 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 5.294 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4432 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating-anode generator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3291 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1781 _reflns_number_gt 1565 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2002)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2002)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2002)' _computing_structure_solution 'Siemens SHELXTL^TM^ 5' _computing_structure_refinement 'Siemens SHELXTL^TM^ 5' _computing_molecular_graphics 'Siemens SHELXTL^TM^ 5' _computing_publication_material 'Siemens SHELXTL^TM^ 5' _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^)+(0.0940P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1781 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1334 _refine_ls_wR_factor_gt 0.1299 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.09606(15) -0.13594(17) -0.11392(9) 0.0492(3) Uani 1 1 d . . . I1 I -0.07629(7) -0.19539(6) -0.33380(4) 0.0360(2) Uani 1 1 d . . . S1 S -0.1402(3) -0.2124(3) 0.02018(16) 0.0398(5) Uani 1 1 d . . . N1 N -0.5907(10) -0.1992(9) -0.0774(6) 0.0413(15) Uani 1 1 d . . . N11 N 0.4711(10) 0.6942(7) 0.3143(5) 0.0299(12) Uani 1 1 d . . . C1 C -0.4047(11) -0.2029(9) -0.0400(6) 0.0312(15) Uani 1 1 d . . . C11 C 0.6242(15) 0.5428(11) 0.3174(8) 0.050(2) Uani 1 1 d . . . H11A H 0.7132 0.5283 0.2508 0.075 Uiso 1 1 calc R . . H11B H 0.5352 0.4365 0.3127 0.075 Uiso 1 1 calc R . . H11C H 0.7229 0.5661 0.3906 0.075 Uiso 1 1 calc R . . C12 C 0.3132(16) 0.6581(14) 0.2018(7) 0.059(2) Uani 1 1 d . . . H12A H 0.3993 0.6420 0.1341 0.089 Uiso 1 1 calc R . . H12B H 0.2156 0.7564 0.2004 0.089 Uiso 1 1 calc R . . H12C H 0.2232 0.5527 0.1985 0.089 Uiso 1 1 calc R . . C13 C 0.3341(14) 0.7178(11) 0.4184(7) 0.0446(19) Uani 1 1 d . . . H13A H 0.2441 0.6121 0.4141 0.067 Uiso 1 1 calc R . . H13B H 0.2364 0.8160 0.4168 0.067 Uiso 1 1 calc R . . H13C H 0.4337 0.7405 0.4913 0.067 Uiso 1 1 calc R . . C14 C 0.6104(15) 0.8592(11) 0.3210(8) 0.047(2) Uani 1 1 d . . . H14A H 0.7001 0.8437 0.2548 0.071 Uiso 1 1 calc R . . H14B H 0.7083 0.8832 0.3945 0.071 Uiso 1 1 calc R . . H14C H 0.5121 0.9568 0.3182 0.071 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 0.0192(5) 0.0864(8) 0.0417(6) 0.0148(5) -0.0015(4) 0.0016(5) I1 0.0326(3) 0.0408(3) 0.0325(3) 0.0066(2) -0.0047(2) -0.0031(2) S1 0.0196(9) 0.0672(13) 0.0328(10) 0.0130(9) -0.0016(7) 0.0022(8) N1 0.027(4) 0.047(4) 0.044(4) -0.003(3) 0.003(3) 0.000(3) N11 0.031(3) 0.027(3) 0.030(3) 0.004(2) 0.001(2) 0.000(2) C1 0.019(4) 0.041(4) 0.031(4) 0.001(3) 0.002(3) -0.003(3) C11 0.048(5) 0.040(4) 0.059(5) 0.002(4) 0.003(4) 0.009(4) C12 0.062(6) 0.073(6) 0.038(5) 0.012(4) -0.020(4) -0.014(5) C13 0.049(5) 0.050(5) 0.035(4) 0.003(3) 0.015(4) 0.000(4) C14 0.044(5) 0.039(4) 0.058(5) 0.006(4) 0.012(4) -0.009(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 1.953(7) 1_655 ? Cu1 S1 2.337(3) . ? Cu1 I1 2.579(2) . ? Cu1 S1 2.684(3) 2 ? S1 C1 1.659(7) . ? S1 Cu1 2.684(3) 2 ? N1 C1 1.147(8) . ? N1 Cu1 1.953(7) 1_455 ? N11 C11 1.490(9) . ? N11 C13 1.493(9) . ? N11 C14 1.494(10) . ? N11 C12 1.496(9) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 S1 111.7(2) 1_655 . ? N1 Cu1 I1 118.95(19) 1_655 . ? S1 Cu1 I1 115.08(8) . . ? N1 Cu1 S1 98.2(2) 1_655 2 ? S1 Cu1 S1 97.79(9) . 2 ? I1 Cu1 S1 111.57(6) . 2 ? C1 S1 Cu1 106.8(3) . . ? C1 S1 Cu1 94.8(3) . 2 ? Cu1 S1 Cu1 82.21(9) . 2 ? C1 N1 Cu1 165.8(6) . 1_455 ? C11 N11 C13 109.5(6) . . ? C11 N11 C14 109.3(6) . . ? C13 N11 C14 109.4(6) . . ? C11 N11 C12 110.0(6) . . ? C13 N11 C12 108.7(6) . . ? C14 N11 C12 110.0(7) . . ? N1 C1 S1 176.9(7) . . ? N11 C11 H11A 109.5 . . ? N11 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N11 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N11 C12 H12A 109.5 . . ? N11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N11 C13 H13A 109.5 . . ? N11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N11 C14 H14A 109.5 . . ? N11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 3.812 _refine_diff_density_min -1.091 _refine_diff_density_rms 0.220 #===END data_Comp3 _database_code_depnum_ccdc_archive 'CCDC 714861' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H12 Ag2 Cl N3 O0 S2' _chemical_formula_weight 441.50 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' 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pmn2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y, z+1/2' '-x, y, z' _cell_length_a 14.900(4) _cell_length_b 6.4724(13) _cell_length_c 6.4724(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 624.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1829 _cell_measurement_theta_min 3.1484 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Prism _exptl_crystal_colour Red _exptl_crystal_size_max 0.5000 _exptl_crystal_size_mid 0.3000 _exptl_crystal_size_min 0.3000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 3.652 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6075 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating-anode generator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3901 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1096 _reflns_number_gt 1066 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2002)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2002)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2002)' _computing_structure_solution 'Siemens SHELXTL^TM^ 5' _computing_structure_refinement 'Siemens SHELXTL^TM^ 5' _computing_molecular_graphics 'Siemens SHELXTL^TM^ 5' _computing_publication_material 'Siemens SHELXTL^TM^ 5' _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^)+(0.0458P)^2^+0.4000P] 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 SHELXL _refine_ls_extinction_coef 0.0193(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(12) _refine_ls_number_reflns 1096 _refine_ls_number_parameters 72 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0671 _refine_ls_wR_factor_gt 0.0664 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 Ag1 Ag 0.165595(10) 0.37425(2) 0.55508(5) 0.05451(6) Uani 1 1 d . . . Cl1 Cl 0.0000 0.48249(10) 0.53915(15) 0.04145(17) Uani 1 2 d S . . S1 S 0.22054(4) 0.34518(7) 0.97958(9) 0.03780(14) Uani 1 1 d . . . N1 N 0.30986(13) -0.0357(2) 0.9969(3) 0.0397(5) Uani 1 1 d . . . C1 C 0.27465(15) 0.1215(2) 0.9904(3) 0.0300(6) Uani 1 1 d . . . N2 N 0.0000 0.8896(3) 0.0252(4) 0.0303(6) Uani 1 2 d S . . C2 C 0.08118(14) 0.7573(4) 0.0401(7) 0.0624(7) Uani 1 1 d . . . H2A H 0.0822 0.6621 -0.0736 0.094 Uiso 1 1 calc R . . H2B H 0.0799 0.6818 0.1678 0.094 Uiso 1 1 calc R . . H2C H 0.1339 0.8425 0.0359 0.094 Uiso 1 1 calc R . . C3 C 0.0000 1.0399(6) 0.2008(6) 0.0534(10) Uani 1 2 d S . . H3A H 0.0000 0.9657 0.3293 0.080 Uiso 1 2 calc SR . . H3B H -0.0526 1.1251 0.1929 0.080 Uiso 0.50 1 calc PR . . H3C H 0.0526 1.1251 0.1929 0.080 Uiso 0.50 1 calc PR . . C4 C 0.0000 1.0026(7) -0.1746(6) 0.0642(13) Uani 1 2 d S . . H4A H 0.0000 0.9052 -0.2865 0.096 Uiso 1 2 calc SR . . H4B H 0.0526 1.0878 -0.1832 0.096 Uiso 0.50 1 calc PR . . H4C H -0.0526 1.0878 -0.1832 0.096 Uiso 0.50 1 calc PR . . 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 Ag1 0.03670(9) 0.02475(8) 0.10208(15) -0.00113(9) 0.00033(14) 0.00157(5) Cl1 0.0259(3) 0.0376(3) 0.0609(4) -0.0012(4) 0.000 0.000 S1 0.0331(2) 0.02303(19) 0.0572(3) -0.0018(2) -0.0085(2) 0.00197(19) N1 0.0480(9) 0.0200(7) 0.0511(12) 0.0004(8) 0.0032(8) 0.0059(7) C1 0.0284(10) 0.0275(10) 0.0342(11) -0.0001(8) 0.0016(7) -0.0054(7) N2 0.0211(9) 0.0319(10) 0.0378(15) -0.0003(10) 0.000 0.000 C2 0.0415(10) 0.0652(13) 0.0806(15) -0.0109(16) -0.0086(17) 0.0218(10) C3 0.0514(19) 0.055(2) 0.054(2) -0.0168(18) 0.000 0.000 C4 0.085(3) 0.062(2) 0.046(2) 0.0208(19) 0.000 0.000 _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 Ag1 N1 2.2534(16) 2_554 ? Ag1 S1 2.5328(7) 2_564 ? Ag1 Cl1 2.5670(7) . ? Ag1 S1 2.8731(8) . ? Cl1 Ag1 2.5670(7) 4 ? S1 C1 1.6588(18) . ? S1 Ag1 2.5328(7) 2_565 ? N1 C1 1.145(2) . ? N1 Ag1 2.2534(16) 2 ? N2 C2 1.485(3) 4 ? N2 C2 1.485(3) . ? N2 C4 1.486(5) . ? N2 C3 1.496(4) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? 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 Ag1 S1 123.80(5) 2_554 2_564 ? N1 Ag1 Cl1 114.50(5) 2_554 . ? S1 Ag1 Cl1 116.13(3) 2_564 . ? N1 Ag1 S1 92.86(4) 2_554 . ? S1 Ag1 S1 92.326(17) 2_564 . ? Cl1 Ag1 S1 109.28(3) . . ? Ag1 Cl1 Ag1 147.98(3) . 4 ? C1 S1 Ag1 106.98(8) . 2_565 ? C1 S1 Ag1 103.66(7) . . ? Ag1 S1 Ag1 109.17(2) 2_565 . ? C1 N1 Ag1 160.76(17) . 2 ? N1 C1 S1 178.1(2) . . ? C2 N2 C2 109.1(2) 4 . ? C2 N2 C4 109.9(2) 4 . ? C2 N2 C4 109.9(2) . . ? C2 N2 C3 109.0(2) 4 . ? C2 N2 C3 109.0(2) . . ? C4 N2 C3 110.0(3) . . ? N2 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.513 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.086