# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_nrb19 _audit_creation_date 2013-10-21 _audit_creation_method ; Olex2 1.2-beta (compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H26 N4 Ni O4' _chemical_formula_sum 'C16 H26 N4 Ni O4' _chemical_formula_weight 397.12 _chemical_melting_point ? _chemical_oxdiff_formula 'C10 H10 N2 Ni C H3 C O2' 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' Ni Ni 0.3393 1.1124 '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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.4371(15) _cell_length_b 9.820(1) _cell_length_c 15.9240(19) _cell_angle_alpha 90.00 _cell_angle_beta 97.565(12) _cell_angle_gamma 90.00 _cell_volume 1927.9(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1307 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 28.7399 _cell_measurement_theta_min 2.8474 _exptl_absorpt_coefficient_mu 1.033 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.53135 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 840 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_unetI/netI 0.0688 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4251 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 28.72 _diffrn_reflns_theta_min 2.85 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9631 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.881 _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0311803000 _diffrn_orient_matrix_UB_12 -0.0540271000 _diffrn_orient_matrix_UB_13 -0.0137746000 _diffrn_orient_matrix_UB_21 -0.0206838000 _diffrn_orient_matrix_UB_22 0.0148257000 _diffrn_orient_matrix_UB_23 -0.0426934000 _diffrn_orient_matrix_UB_31 0.0437453000 _diffrn_orient_matrix_UB_32 0.0455831000 _diffrn_orient_matrix_UB_33 -0.0024253000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'SuperNova (Mo) X-ray Source' _reflns_number_gt 1261 _reflns_number_total 2205 _reflns_odcompleteness_completeness 99.76 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELX, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.461 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.070 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 117 _refine_ls_number_reflns 2205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1114 _refine_ls_R_factor_gt 0.0632 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0845P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1561 _refine_ls_wR_factor_ref 0.1954 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C6(H6A,H6B) 2.b Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5) 2.c Idealised Me refined as rotating group: C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Ni1 Ni 1.0000 0.13710(7) 0.2500 0.0640(4) Uani 1 2 d S . . N1 N 0.8157(3) -0.0270(4) 0.1821(3) 0.0744(10) Uani 1 1 d . . . C2 C 0.9213(3) 0.0051(4) 0.1838(3) 0.0624(11) Uani 1 1 d . . . N3 N 0.9547(3) -0.0762(4) 0.1228(2) 0.0730(10) Uani 1 1 d . . . C4 C 0.8689(5) -0.1561(5) 0.0847(4) 0.0905(16) Uani 1 1 d . . . H4 H 0.8715 -0.2189 0.0414 0.109 Uiso 1 1 calc R . . C5 C 0.7843(5) -0.1256(6) 0.1217(4) 0.0933(17) Uani 1 1 d . . . H5 H 0.7154 -0.1633 0.1096 0.112 Uiso 1 1 calc R . . C6 C 0.7456(4) 0.0359(7) 0.2340(4) 0.0988(17) Uani 1 1 d . . . H6A H 0.7877 0.0983 0.2725 0.119 Uiso 1 1 calc R . . H6B H 0.7166 -0.0337 0.2680 0.119 Uiso 1 1 calc R . . C7 C 0.6572(9) 0.1089(8) 0.1883(7) 0.180(4) Uani 1 1 d . . . H7A H 0.6707 0.1218 0.1308 0.270 Uiso 1 1 calc R . . H7B H 0.6502 0.1959 0.2144 0.270 Uiso 1 1 calc R . . H7C H 0.5914 0.0580 0.1888 0.270 Uiso 1 1 calc R . . C8 C 1.0639(4) -0.0769(6) 0.0981(4) 0.0984(17) Uani 1 1 d . . . H8A H 1.0965 0.0111 0.1088 0.148 Uiso 1 1 calc R . . H8B H 1.0598 -0.0977 0.0389 0.148 Uiso 1 1 calc R . . H8C H 1.1072 -0.1444 0.1304 0.148 Uiso 1 1 calc R . . O9 O 1.0820(2) 0.2760(3) 0.3155(2) 0.0741(9) Uani 1 1 d . . . C10 C 1.0493(4) 0.3135(5) 0.3841(3) 0.0678(12) Uani 1 1 d . . . O11 O 0.9697(3) 0.2681(3) 0.4112(2) 0.0880(10) Uani 1 1 d . . . C12 C 1.1197(5) 0.4191(6) 0.4341(4) 0.113(2) Uani 1 1 d . . . H12A H 1.1940 0.3899 0.4404 0.169 Uiso 1 1 calc R . . H12B H 1.0969 0.4297 0.4890 0.169 Uiso 1 1 calc R . . H12C H 1.1129 0.5045 0.4046 0.169 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 Ni1 0.0651(5) 0.0713(6) 0.0570(6) 0.000 0.0133(4) 0.000 N1 0.067(2) 0.091(3) 0.067(3) 0.001(2) 0.013(2) -0.009(2) C2 0.067(3) 0.065(2) 0.056(3) 0.006(2) 0.009(2) 0.0000(19) N3 0.079(2) 0.079(2) 0.061(2) -0.004(2) 0.0091(19) 0.003(2) C4 0.107(4) 0.080(3) 0.080(4) -0.015(3) -0.003(3) -0.012(3) C5 0.083(4) 0.116(4) 0.078(4) 0.002(3) 0.002(3) -0.027(3) C6 0.075(3) 0.134(5) 0.090(4) 0.008(4) 0.019(3) -0.008(3) C7 0.187(10) 0.170(7) 0.176(10) -0.020(7) -0.007(8) 0.028(6) C8 0.093(4) 0.122(4) 0.082(4) -0.022(3) 0.019(3) 0.012(3) O9 0.0758(19) 0.0794(19) 0.071(2) -0.0104(17) 0.0237(16) -0.0141(15) C10 0.067(3) 0.074(3) 0.065(3) -0.002(3) 0.019(2) 0.002(2) O11 0.078(2) 0.100(2) 0.092(3) 0.000(2) 0.0362(19) -0.0038(18) C12 0.118(5) 0.131(5) 0.097(5) -0.037(4) 0.040(4) -0.030(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 Ni1 C2 1.865(4) 2_755 ? Ni1 C2 1.865(4) . ? Ni1 O9 1.926(3) 2_755 ? Ni1 O9 1.926(3) . ? N1 C2 1.347(5) . ? N1 C5 1.384(6) . ? N1 C6 1.419(7) . ? C2 N3 1.364(5) . ? N3 C4 1.397(6) . ? N3 C8 1.463(6) . ? C4 C5 1.306(9) . ? C6 C7 1.429(10) . ? O9 C10 1.270(5) . ? C10 O11 1.215(5) . ? C10 C12 1.514(7) . ? 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 C2 Ni1 C2 91.9(2) . 2_755 ? C2 Ni1 O9 89.15(17) . 2_755 ? C2 Ni1 O9 178.41(15) 2_755 2_755 ? C2 Ni1 O9 178.41(15) . . ? C2 Ni1 O9 89.15(17) 2_755 . ? O9 Ni1 O9 89.80(19) . 2_755 ? C2 N1 C5 111.2(4) . . ? C2 N1 C6 123.9(4) . . ? C5 N1 C6 124.8(5) . . ? N1 C2 Ni1 127.7(4) . . ? N1 C2 N3 103.7(4) . . ? N3 C2 Ni1 128.5(3) . . ? C2 N3 C4 110.5(4) . . ? C2 N3 C8 125.1(4) . . ? C4 N3 C8 124.3(5) . . ? C5 C4 N3 106.9(5) . . ? C4 C5 N1 107.7(5) . . ? N1 C6 C7 114.3(6) . . ? C10 O9 Ni1 117.7(3) . . ? O9 C10 C12 115.0(4) . . ? O11 C10 O9 124.6(5) . . ? O11 C10 C12 120.4(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 N3 0.0(5) . . . . ? C6 N1 C2 N3 -178.1(4) . . . . ? C5 N1 C2 Ni1 176.8(3) . . . . ? C6 N1 C2 Ni1 -1.3(7) . . . . ? C2 Ni1 C2 N1 109.7(4) 2_755 . . . ? O9 Ni1 C2 N1 -69.1(4) 2_755 . . . ? C2 Ni1 C2 N3 -74.3(4) 2_755 . . . ? O9 Ni1 C2 N3 106.9(4) 2_755 . . . ? N1 C2 N3 C4 0.2(5) . . . . ? Ni1 C2 N3 C4 -176.5(3) . . . . ? N1 C2 N3 C8 178.1(4) . . . . ? Ni1 C2 N3 C8 1.4(7) . . . . ? C2 N3 C4 C5 -0.4(6) . . . . ? C8 N3 C4 C5 -178.3(5) . . . . ? N3 C4 C5 N1 0.4(6) . . . . ? C2 N1 C5 C4 -0.2(6) . . . . ? C6 N1 C5 C4 177.9(5) . . . . ? C2 N1 C6 C7 117.2(6) . . . . ? C5 N1 C6 C7 -60.7(8) . . . . ? C2 Ni1 O9 C10 -85.2(3) 2_755 . . . ? O9 Ni1 O9 C10 93.6(3) 2_755 . . . ? Ni1 O9 C10 O11 -0.2(6) . . . . ? Ni1 O9 C10 C12 177.8(4) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 968222' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_nrb22 _audit_creation_date 2013-10-21 _audit_creation_method ; Olex2 1.2-beta (compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H20 Ag N4, C2 N3' _chemical_formula_sum 'C14 H20 Ag N7' _chemical_formula_weight 394.24 _chemical_melting_point 377 _chemical_oxdiff_formula 'C8 H11 N5 Ag' 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' Ag Ag -0.8971 1.1015 '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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.344(2) _cell_length_b 6.9249(4) _cell_length_c 15.2990(17) _cell_angle_alpha 90.00 _cell_angle_beta 126.766(16) _cell_angle_gamma 90.00 _cell_volume 1726.6(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1267 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.2263 _cell_measurement_theta_min 3.1899 _exptl_absorpt_coefficient_mu 1.175 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.91554 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 800 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_unetI/netI 0.0419 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 3572 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 29.29 _diffrn_reflns_theta_min 3.20 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9631 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.840 _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0140896000 _diffrn_orient_matrix_UB_12 -0.0180707000 _diffrn_orient_matrix_UB_13 -0.0318729000 _diffrn_orient_matrix_UB_21 0.0354196000 _diffrn_orient_matrix_UB_22 0.0567586000 _diffrn_orient_matrix_UB_23 0.0364201000 _diffrn_orient_matrix_UB_31 0.0210701000 _diffrn_orient_matrix_UB_32 -0.0832649000 _diffrn_orient_matrix_UB_33 0.0317466000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'SuperNova (Mo) X-ray Source' _reflns_number_gt 1303 _reflns_number_total 1981 _reflns_odcompleteness_completeness 99.74 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELX, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELX, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.340 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.063 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 104 _refine_ls_number_reflns 1981 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0360 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0332P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0743 _refine_ls_wR_factor_ref 0.0901 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C6(H6A,H6B) 2.b Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5) 2.c Idealised Me refined as rotating group: C7(H7A,H7B,H7C), C8(H8A,H8B,H8C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.0000 0.5000 0.0000 0.06008(17) Uani 1 2 d S . . N1 N 0.14903(17) 0.7523(4) 0.0668(2) 0.0604(7) Uani 1 1 d . . . C2 C 0.0669(2) 0.7249(5) -0.0011(3) 0.0576(9) Uani 1 1 d . . . N3 N 0.03861(17) 0.8824(4) -0.0668(2) 0.0603(7) Uani 1 1 d . . . C4 C 0.1025(3) 1.0004(5) -0.0399(4) 0.0723(11) Uani 1 1 d . . . H4 H 0.0982 1.1161 -0.0739 0.087 Uiso 1 1 calc R . . C5 C 0.1714(2) 0.9201(7) 0.0430(3) 0.0737(10) Uani 1 1 d . . . H5 H 0.2244 0.9677 0.0782 0.088 Uiso 1 1 calc R . . C6 C 0.2077(2) 0.6140(6) 0.1502(3) 0.0763(11) Uani 1 1 d . . . H6A H 0.1812 0.5421 0.1757 0.092 Uiso 1 1 calc R . . H6B H 0.2535 0.6840 0.2118 0.092 Uiso 1 1 calc R . . C7 C 0.2389(4) 0.4773(6) 0.1090(5) 0.1077(18) Uani 1 1 d . . . H7A H 0.1936 0.4097 0.0468 0.161 Uiso 1 1 calc R . . H7B H 0.2750 0.3862 0.1652 0.161 Uiso 1 1 calc R . . H7C H 0.2682 0.5469 0.0880 0.161 Uiso 1 1 calc R . . C8 C -0.0476(2) 0.9181(6) -0.1554(3) 0.0741(11) Uani 1 1 d . . . H8A H -0.0584 1.0542 -0.1610 0.111 Uiso 1 1 calc R . . H8B H -0.0815 0.8516 -0.1407 0.111 Uiso 1 1 calc R . . H8C H -0.0596 0.8719 -0.2227 0.111 Uiso 1 1 calc R . . N9 N 0.1253(2) 0.5121(5) 0.2974(4) 0.1065(15) Uani 1 1 d . . . C10 C 0.0653(3) 0.5664(6) 0.2751(3) 0.0692(10) Uani 1 1 d . . . N11 N 0.0000 0.6525(7) 0.2500 0.117(2) Uani 1 2 d S . . 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 0.0499(2) 0.0647(3) 0.0658(3) 0.00000(17) 0.0347(2) -0.00607(17) N1 0.0450(16) 0.0786(19) 0.0545(17) 0.0063(15) 0.0282(14) -0.0025(15) C2 0.0444(19) 0.073(2) 0.0526(19) -0.0039(18) 0.0277(16) -0.0042(18) N3 0.0451(17) 0.0700(19) 0.0552(16) 0.0005(16) 0.0244(14) -0.0068(15) C4 0.068(3) 0.076(3) 0.071(3) 0.0040(19) 0.040(2) -0.019(2) C5 0.050(2) 0.097(3) 0.067(3) -0.004(2) 0.031(2) -0.023(2) C6 0.049(2) 0.107(3) 0.063(2) 0.013(2) 0.0280(19) 0.006(2) C7 0.102(4) 0.114(4) 0.092(4) 0.013(3) 0.050(3) 0.032(3) C8 0.054(2) 0.082(2) 0.066(2) 0.008(2) 0.025(2) 0.000(2) N9 0.058(2) 0.143(4) 0.107(3) -0.009(2) 0.043(3) -0.003(2) C10 0.060(3) 0.076(2) 0.067(3) -0.012(2) 0.036(2) -0.011(2) N11 0.108(5) 0.066(3) 0.205(6) 0.000 0.109(5) 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 C2 2.075(3) 5_565 ? Ag1 C2 2.075(3) . ? N1 C2 1.352(4) . ? N1 C5 1.374(4) . ? N1 C6 1.465(4) . ? C2 N3 1.355(4) . ? N3 C4 1.374(4) . ? N3 C8 1.459(4) . ? C4 C5 1.325(5) . ? C6 C7 1.475(6) . ? N9 C10 1.118(5) . ? C10 N11 1.286(5) . ? N11 C10 1.286(5) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 Ag1 C2 180.00(17) 5_565 . ? C2 N1 C5 111.6(3) . . ? C2 N1 C6 124.4(3) . . ? C5 N1 C6 123.8(3) . . ? N1 C2 Ag1 127.8(3) . . ? N1 C2 N3 103.8(3) . . ? N3 C2 Ag1 128.3(2) . . ? C2 N3 C4 110.5(3) . . ? C2 N3 C8 124.5(3) . . ? C4 N3 C8 125.0(3) . . ? C5 C4 N3 107.8(3) . . ? C4 C5 N1 106.2(3) . . ? N1 C6 C7 112.4(3) . . ? N9 C10 N11 172.0(5) . . ? C10 N11 C10 124.8(6) . 2 ? 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 Ag1 C2 N3 C4 178.5(2) . . . . ? Ag1 C2 N3 C8 -3.1(5) . . . . ? N1 C2 N3 C4 0.9(4) . . . . ? N1 C2 N3 C8 179.3(3) . . . . ? C2 N1 C5 C4 0.7(5) . . . . ? C2 N1 C6 C7 91.2(5) . . . . ? C2 N3 C4 C5 -0.5(5) . . . . ? N3 C4 C5 N1 -0.2(5) . . . . ? C5 N1 C2 Ag1 -178.6(3) . . . . ? C5 N1 C2 N3 -1.0(4) . . . . ? C5 N1 C6 C7 -84.1(5) . . . . ? C6 N1 C2 Ag1 5.5(5) . . . . ? C6 N1 C2 N3 -176.9(3) . . . . ? C6 N1 C5 C4 176.6(3) . . . . ? C8 N3 C4 C5 -178.9(4) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 968223' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_nrb23 _audit_creation_date 2013-10-21 _audit_creation_method ; Olex2 1.2-beta (compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H20 Ag N4, C N S' _chemical_formula_sum 'C13 H20 Ag N5 S' _chemical_formula_weight 386.27 _chemical_melting_point 381 _chemical_oxdiff_formula 'C13 H22 N5 S Ag' 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' Ag Ag -0.8971 1.1015 '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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.7075(11) _cell_length_b 8.1360(5) _cell_length_c 13.3162(8) _cell_angle_alpha 90.00 _cell_angle_beta 111.810(7) _cell_angle_gamma 90.00 _cell_volume 1680.53(18) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6030 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.0350 _cell_measurement_theta_min 2.8214 _exptl_absorpt_coefficient_mu 1.321 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.77307 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_unetI/netI 0.0155 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 10704 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 29.10 _diffrn_reflns_theta_min 2.83 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9631 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.916 _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0114050000 _diffrn_orient_matrix_UB_12 -0.0783020000 _diffrn_orient_matrix_UB_13 0.0138897000 _diffrn_orient_matrix_UB_21 0.0392750000 _diffrn_orient_matrix_UB_22 -0.0329072000 _diffrn_orient_matrix_UB_23 -0.0001314000 _diffrn_orient_matrix_UB_31 0.0204544000 _diffrn_orient_matrix_UB_32 0.0195442000 _diffrn_orient_matrix_UB_33 0.0556864000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'SuperNova (Mo) X-ray Source' _reflns_number_gt 1848 _reflns_number_total 2066 _reflns_odcompleteness_completeness 99.78 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELX, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELX, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.684 _refine_diff_density_min -0.554 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 106 _refine_ls_number_reflns 2066 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0266 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0216P)^2^+1.7387P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.0600 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All C(H,H,H,H,H,H) groups 2. Others Fixed Sof: H8A(0.5) H8B(0.5) H8C(0.5) H8D(0.5) H8E(0.5) H8F(0.5) S9(0.5) C10(0.5) N11(0.5) 3.a Secondary CH2 refined with riding coordinates: C6(H6A,H6B) 3.b Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5) 3.c Disordered Me refined with riding coordinates: C8(H8A,H8B,H8C,H8D,H8E,H8F) 3.d Idealised Me refined as rotating group: C7(H7A,H7B,H7C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.5000 0.11547(3) 0.7500 0.05832(10) Uani 1 2 d S . . N1 N 0.65933(11) 0.0649(2) 0.68516(13) 0.0520(4) Uani 1 1 d . . . C2 C 0.57738(14) 0.1165(2) 0.65812(16) 0.0488(4) Uani 1 1 d . . . N3 N 0.55746(11) 0.1843(2) 0.55934(13) 0.0498(4) Uani 1 1 d . . . C4 C 0.62588(15) 0.1740(3) 0.52582(18) 0.0612(6) Uani 1 1 d . . . H4 H 0.6273 0.2119 0.4606 0.073 Uiso 1 1 calc R . . C5 C 0.68960(15) 0.0996(3) 0.60450(19) 0.0629(6) Uani 1 1 d . . . H5 H 0.7441 0.0757 0.6049 0.075 Uiso 1 1 calc R . . C6 C 0.71001(17) -0.0138(3) 0.78789(19) 0.0697(6) Uani 1 1 d . . . H6A H 0.7548 -0.0803 0.7781 0.084 Uiso 1 1 calc R . . H6B H 0.6729 -0.0865 0.8089 0.084 Uiso 1 1 calc R . . C7 C 0.7504(2) 0.1063(4) 0.8759(2) 0.0954(10) Uani 1 1 d . . . H7A H 0.7874 0.1786 0.8558 0.143 Uiso 1 1 calc R . . H7B H 0.7838 0.0488 0.9410 0.143 Uiso 1 1 calc R . . H7C H 0.7063 0.1694 0.8881 0.143 Uiso 1 1 calc R . . C8 C 0.47452(15) 0.2586(3) 0.49705(19) 0.0661(6) Uani 1 1 d . . . H8A H 0.4753 0.2986 0.4296 0.099 Uiso 0.50 1 calc PR . . H8B H 0.4638 0.3484 0.5372 0.099 Uiso 0.50 1 calc PR . . H8C H 0.4298 0.1779 0.4833 0.099 Uiso 0.50 1 calc PR . . H8D H 0.4373 0.2513 0.5372 0.099 Uiso 0.50 1 calc PR . . H8E H 0.4487 0.2015 0.4295 0.099 Uiso 0.50 1 calc PR . . H8F H 0.4828 0.3720 0.4834 0.099 Uiso 0.50 1 calc PR . . S9 S 0.5769(2) 0.5224(3) 0.7873(3) 0.0820(6) Uani 0.50 1 d P A -1 C10 C 0.4744(4) 0.5578(9) 0.7349(5) 0.0679(15) Uani 0.50 1 d P A -1 N11 N 0.4061(7) 0.5882(14) 0.7000(9) 0.116(4) Uani 0.50 1 d P A -1 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 0.06180(16) 0.07021(18) 0.05122(14) 0.000 0.03059(11) 0.000 N1 0.0495(10) 0.0593(10) 0.0453(9) -0.0054(8) 0.0153(7) -0.0059(8) C2 0.0535(11) 0.0498(11) 0.0445(10) -0.0084(8) 0.0197(9) -0.0090(9) N3 0.0513(9) 0.0552(10) 0.0425(8) -0.0064(7) 0.0169(7) -0.0068(8) C4 0.0640(14) 0.0774(15) 0.0481(11) -0.0063(11) 0.0278(10) -0.0156(12) C5 0.0514(12) 0.0839(17) 0.0590(13) -0.0100(12) 0.0269(10) -0.0086(11) C6 0.0653(14) 0.0766(17) 0.0597(13) 0.0067(12) 0.0145(11) 0.0016(13) C7 0.104(2) 0.109(2) 0.0495(14) 0.0042(14) 0.0011(15) -0.0171(19) C8 0.0648(14) 0.0681(15) 0.0586(13) 0.0004(11) 0.0153(11) 0.0023(12) S9 0.0625(14) 0.0965(16) 0.0845(13) -0.0114(12) 0.0244(12) 0.0008(12) C10 0.056(4) 0.096(4) 0.054(4) 0.007(3) 0.022(4) -0.002(3) N11 0.084(6) 0.160(10) 0.112(6) 0.054(6) 0.047(4) 0.032(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 Ag1 C2 2.084(2) 2_656 ? Ag1 C2 2.084(2) . ? N1 C2 1.347(3) . ? N1 C5 1.376(3) . ? N1 C6 1.462(3) . ? C2 N3 1.349(3) . ? N3 C4 1.376(3) . ? N3 C8 1.456(3) . ? C4 C5 1.330(4) . ? C6 C7 1.483(4) . ? S9 C10 1.617(8) . ? C10 N11 1.089(11) . ? 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 C2 Ag1 C2 179.56(11) 2_656 . ? C2 N1 C5 111.06(18) . . ? C2 N1 C6 124.36(19) . . ? C5 N1 C6 124.6(2) . . ? N1 C2 Ag1 129.24(15) . . ? N1 C2 N3 104.25(17) . . ? N3 C2 Ag1 126.28(16) . . ? C2 N3 C4 110.97(18) . . ? C2 N3 C8 124.27(18) . . ? C4 N3 C8 124.76(19) . . ? C5 C4 N3 106.9(2) . . ? C4 C5 N1 106.8(2) . . ? N1 C6 C7 112.7(2) . . ? N11 C10 S9 177.1(10) . . ? 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 Ag1 C2 N3 C4 175.16(15) . . . . ? Ag1 C2 N3 C8 -4.7(3) . . . . ? N1 C2 N3 C4 0.3(2) . . . . ? N1 C2 N3 C8 -179.58(19) . . . . ? C2 N1 C5 C4 0.0(3) . . . . ? C2 N1 C6 C7 -83.0(3) . . . . ? C2 N3 C4 C5 -0.2(3) . . . . ? N3 C4 C5 N1 0.1(3) . . . . ? C5 N1 C2 Ag1 -174.88(16) . . . . ? C5 N1 C2 N3 -0.2(2) . . . . ? C5 N1 C6 C7 95.4(3) . . . . ? C6 N1 C2 Ag1 3.7(3) . . . . ? C6 N1 C2 N3 178.4(2) . . . . ? C6 N1 C5 C4 -178.5(2) . . . . ? C8 N3 C4 C5 179.6(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 968224' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_nrb118-rt _audit_creation_date 2013-10-21 _audit_creation_method ; Olex2 1.2-beta (compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H20 Ag N4, C2 H3 O2' _chemical_formula_sum 'C14 H23 Ag N4 O2' _chemical_formula_weight 387.23 _chemical_melting_point 367 _chemical_oxdiff_formula 'Ag C14 H32 N4 O2' 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' Ag Ag -0.8971 1.1015 '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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.4432(7) _cell_length_b 8.6443(4) _cell_length_c 13.5597(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.450(5) _cell_angle_gamma 90.00 _cell_volume 1717.13(13) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2643 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 28.8210 _cell_measurement_theta_min 3.4880 _exptl_absorpt_coefficient_mu 1.183 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.66619 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0127 _diffrn_reflns_av_unetI/netI 0.0197 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 3891 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 29.14 _diffrn_reflns_theta_min 2.93 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9631 _diffrn_measured_fraction_theta_full 0.9973 _diffrn_measured_fraction_theta_max 0.5121 _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0147787000 _diffrn_orient_matrix_UB_12 -0.0690068000 _diffrn_orient_matrix_UB_13 0.0180733000 _diffrn_orient_matrix_UB_21 0.0370084000 _diffrn_orient_matrix_UB_22 0.0052863000 _diffrn_orient_matrix_UB_23 0.0468264000 _diffrn_orient_matrix_UB_31 -0.0275392000 _diffrn_orient_matrix_UB_32 0.0441514000 _diffrn_orient_matrix_UB_33 0.0226660000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'SuperNova (Mo) X-ray Source' _reflns_number_gt 1810 _reflns_number_total 1974 _reflns_odcompleteness_completeness 99.73 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELX, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELX, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.407 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 99 _refine_ls_number_reflns 1974 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0237 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+0.2081P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0610 _refine_ls_wR_factor_ref 0.0643 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Others Fixed Sof: H11A(0.5) H11B(0.5) H11C(0.5) 3.a Secondary CH2 refined with riding coordinates: C6(H6A,H6B) 3.b Me refined with riding coordinates: C11(H11A,H11B,H11C) 3.c Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5) 3.d Idealised Me refined as rotating group: C7(H7A,H7B,H7C), C8(H8A,H8B,H8C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.0000 0.44832(2) 0.2500 0.05360(10) Uani 1 2 d S . . N1 N 0.17822(12) 0.44552(17) 0.18804(14) 0.0495(4) Uani 1 1 d . . . C2 C 0.08868(13) 0.4086(2) 0.16221(15) 0.0460(4) Uani 1 1 d . . . N3 N 0.06985(11) 0.34174(18) 0.06832(12) 0.0481(4) Uani 1 1 d . . . C4 C 0.14617(15) 0.3372(3) 0.03537(17) 0.0575(5) Uani 1 1 d . . . H4 H 0.1494 0.2976 -0.0271 0.069 Uiso 1 1 calc R . . C5 C 0.21362(15) 0.4007(3) 0.11081(18) 0.0603(5) Uani 1 1 d . . . H5 H 0.2737 0.4129 0.1116 0.072 Uiso 1 1 calc R . . C6 C 0.23056(16) 0.5175(3) 0.28569(19) 0.0643(6) Uani 1 1 d . . . H6A H 0.1909 0.5853 0.3090 0.077 Uiso 1 1 calc R . . H6B H 0.2787 0.5801 0.2745 0.077 Uiso 1 1 calc R . . C7 C 0.2718(3) 0.4002(4) 0.3682(2) 0.1087(12) Uani 1 1 d . . . H7A H 0.3123 0.3345 0.3461 0.163 Uiso 1 1 calc R . . H7B H 0.2243 0.3389 0.3802 0.163 Uiso 1 1 calc R . . H7C H 0.3054 0.4520 0.4313 0.163 Uiso 1 1 calc R . . C8 C -0.01891(15) 0.2783(3) 0.00871(17) 0.0635(5) Uani 1 1 d . . . H8A H -0.0304 0.2990 -0.0639 0.095 Uiso 1 1 calc R . . H8B H -0.0657 0.3256 0.0312 0.095 Uiso 1 1 calc R . . H8C H -0.0190 0.1686 0.0196 0.095 Uiso 1 1 calc R . . O9 O -0.07044(11) 0.7711(2) 0.20032(15) 0.0853(5) Uani 1 1 d . . . C10 C 0.0000 0.8384(3) 0.2500 0.0458(6) Uani 1 2 d S . . C11 C 0.0000 1.0074(6) 0.2500 0.135(3) Uani 1 2 d S . . H11A H 0.0132 1.0444 0.3200 0.203 Uiso 0.50 1 calc PR A -1 H11B H -0.0589 1.0444 0.2085 0.203 Uiso 0.50 1 calc PR A -1 H11C H 0.0457 1.0444 0.2215 0.203 Uiso 0.50 1 calc PR A -1 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 0.04934(14) 0.06984(18) 0.04591(14) 0.000 0.02118(10) 0.000 N1 0.0440(9) 0.0570(10) 0.0466(10) -0.0013(7) 0.0133(7) 0.0081(6) C2 0.0478(10) 0.0473(10) 0.0440(10) 0.0031(8) 0.0159(8) 0.0071(8) N3 0.0494(8) 0.0507(9) 0.0437(8) 0.0005(7) 0.0140(7) 0.0048(7) C4 0.0602(12) 0.0671(13) 0.0502(11) -0.0028(10) 0.0246(9) 0.0123(10) C5 0.0485(11) 0.0765(14) 0.0609(13) -0.0006(11) 0.0245(10) 0.0122(11) C6 0.0507(12) 0.0783(15) 0.0587(13) -0.0127(12) 0.0098(10) 0.0040(11) C7 0.117(3) 0.120(2) 0.0586(17) -0.0113(18) -0.0157(16) 0.038(2) C8 0.0607(12) 0.0667(13) 0.0583(13) -0.0070(11) 0.0121(10) -0.0037(10) O9 0.0651(10) 0.1016(13) 0.0824(12) -0.0216(11) 0.0138(9) -0.0232(9) C10 0.0443(13) 0.0584(16) 0.0365(13) 0.000 0.0154(10) 0.000 C11 0.116(4) 0.059(2) 0.230(8) 0.000 0.052(5) 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 C2 2.1077(19) 2 ? Ag1 C2 2.1077(19) . ? N1 C2 1.353(3) . ? N1 C5 1.381(3) . ? N1 C6 1.455(3) . ? C2 N3 1.344(2) . ? N3 C4 1.387(3) . ? N3 C8 1.460(3) . ? C4 C5 1.326(3) . ? C6 C7 1.495(4) . ? O9 C10 1.230(2) . ? C10 O9 1.230(2) 2 ? C10 C11 1.460(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 C2 Ag1 C2 161.25(11) 2 . ? C2 N1 C5 110.79(18) . . ? C2 N1 C6 124.37(19) . . ? C5 N1 C6 124.80(19) . . ? N1 C2 Ag1 127.52(15) . . ? N3 C2 Ag1 128.37(14) . . ? N3 C2 N1 104.11(16) . . ? C2 N3 C4 111.48(17) . . ? C2 N3 C8 124.74(17) . . ? C4 N3 C8 123.76(17) . . ? C5 C4 N3 106.26(18) . . ? C4 C5 N1 107.35(19) . . ? N1 C6 C7 112.0(2) . . ? O9 C10 O9 123.5(3) . 2 ? O9 C10 C11 118.24(15) . . ? O9 C10 C11 118.24(15) 2 . ? 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 Ag1 C2 N3 C4 179.60(14) . . . . ? Ag1 C2 N3 C8 -1.7(3) . . . . ? N1 C2 N3 C4 -0.3(2) . . . . ? N1 C2 N3 C8 178.47(17) . . . . ? C2 Ag1 C2 N1 -115.35(16) 2 . . . ? C2 Ag1 C2 N3 64.82(16) 2 . . . ? C2 N1 C5 C4 0.8(3) . . . . ? C2 N1 C6 C7 88.6(3) . . . . ? C2 N3 C4 C5 0.8(2) . . . . ? N3 C4 C5 N1 -0.9(3) . . . . ? C5 N1 C2 Ag1 179.81(15) . . . . ? C5 N1 C2 N3 -0.3(2) . . . . ? C5 N1 C6 C7 -89.0(3) . . . . ? C6 N1 C2 Ag1 1.9(3) . . . . ? C6 N1 C2 N3 -178.24(18) . . . . ? C6 N1 C5 C4 178.7(2) . . . . ? C8 N3 C4 C5 -178.0(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 968225'