# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 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_nrb41 _audit_creation_date 2013-05-23 _audit_creation_method ; Olex2 1.2-beta (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; bis(N-methylimidazole)silver nitrate ; _chemical_formula_moiety 'C8 H12 Ag N4, N O3' _chemical_formula_sum 'C8 H12 Ag N5 O3' _chemical_formula_weight 334.10 _chemical_melting_point ? _chemical_oxdiff_formula 'Ag C8 H16 N5 O3' 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 triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 6.2877(2) _cell_length_b 7.7823(4) _cell_length_c 12.5635(5) _cell_angle_alpha 88.036(4) _cell_angle_beta 89.839(3) _cell_angle_gamma 76.687(4) _cell_volume 597.89(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5396 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.132 _cell_measurement_theta_min 3.088 _exptl_absorpt_coefficient_mu 1.691 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.668 _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_colour_primary colourless _exptl_crystal_density_diffrn 1.856 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 332 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_unetI/netI 0.0171 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 8680 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 29.20 _diffrn_reflns_theta_min 3.09 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 15.9631 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.875 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -39.00 52.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.1513 57.0000 -30.0000 91 #__ type_ start__ end____ width___ exp.time_ 2 omega -86.00 -2.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.1513 -57.0000 -180.0000 84 #__ type_ start__ end____ width___ exp.time_ 3 omega -10.00 22.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.1513 -99.0000 -30.0000 32 #__ type_ start__ end____ width___ exp.time_ 4 omega -86.00 4.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.1513 -57.0000 60.0000 90 #__ type_ start__ end____ width___ exp.time_ 5 omega -86.00 -13.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.1513 -77.0000 -60.0000 73 #__ type_ start__ end____ width___ exp.time_ 6 omega -49.00 47.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0263 -77.0000 90.0000 96 #__ type_ start__ end____ width___ exp.time_ 7 omega 27.00 75.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0263 -124.0000 29.0000 48 #__ type_ start__ end____ width___ exp.time_ 8 omega 15.00 74.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0263 -124.0000 -108.0000 59 #__ type_ start__ end____ width___ exp.time_ 9 omega -22.00 89.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0263 0.0000 90.0000 111 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0539527000 _diffrn_orient_matrix_UB_12 -0.0841893000 _diffrn_orient_matrix_UB_13 0.0214623000 _diffrn_orient_matrix_UB_21 0.0125693000 _diffrn_orient_matrix_UB_22 -0.0333389000 _diffrn_orient_matrix_UB_23 -0.0520514000 _diffrn_orient_matrix_UB_31 0.1018309000 _diffrn_orient_matrix_UB_32 0.0241500000 _diffrn_orient_matrix_UB_33 -0.0046107000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _reflns_number_gt 2517 _reflns_number_total 2842 _reflns_odcompleteness_completeness 99.92 _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 ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.446 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2842 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0247 _refine_ls_restrained_S_all 1.044 _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^)+(0.0317P)^2^+0.1573P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.0662 _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 At 1.5 times of: All C(H,H,H,H,H,H) groups 2. Others Fixed Sof: H6A(0.5) H6B(0.5) H6C(0.5) H6D(0.5) H6E(0.5) H6F(0.5) H12A(0.5) H12B(0.5) H12C(0.5) H12D(0.5) H12E(0.5) H12F(0.5) 3.a Aromatic/amide H refined with riding coordinates: C2(H2), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11) 3.b Disordered Me refined with riding coordinates: C6(H6A,H6B,H6C,H6D,H6E,H6F), C12(H12A,H12B,H12C,H12D,H12E,H12F) ; _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 0.18973(3) 0.42206(3) 0.683686(13) 0.06576(9) Uani 1 1 d . . . N1 N 0.1240(3) 0.5677(3) 0.82485(14) 0.0522(4) Uani 1 1 d . . . C2 C -0.0676(4) 0.6554(3) 0.85807(19) 0.0569(5) Uani 1 1 d . . . H2 H -0.1984 0.6627 0.8219 0.068 Uiso 1 1 calc R . . N3 N -0.0516(3) 0.7323(2) 0.94923(16) 0.0547(4) Uani 1 1 d . . . C4 C 0.1652(4) 0.6912(3) 0.97737(18) 0.0561(5) Uani 1 1 d . . . H4 H 0.2270 0.7260 1.0378 0.067 Uiso 1 1 calc R . . C5 C 0.2702(4) 0.5908(3) 0.89996(17) 0.0535(5) Uani 1 1 d . . . H5 H 0.4202 0.5440 0.8979 0.064 Uiso 1 1 calc R . . C6 C -0.2317(5) 0.8411(4) 1.0083(3) 0.0831(8) Uani 1 1 d . . . H6A H -0.1755 0.8807 1.0716 0.125 Uiso 0.50 1 calc PR . . H6B H -0.3357 0.7725 1.0274 0.125 Uiso 0.50 1 calc PR . . H6C H -0.3020 0.9415 0.9645 0.125 Uiso 0.50 1 calc PR . . H6D H -0.3666 0.8491 0.9707 0.125 Uiso 0.50 1 calc PR . . H6E H -0.2065 0.9573 1.0149 0.125 Uiso 0.50 1 calc PR . . H6F H -0.2401 0.7883 1.0779 0.125 Uiso 0.50 1 calc PR . . N7 N 0.2610(3) 0.3006(3) 0.53526(14) 0.0551(4) Uani 1 1 d . . . C8 C 0.4436(3) 0.2729(3) 0.48081(17) 0.0525(5) Uani 1 1 d . . . H8 H 0.5642 0.3164 0.4987 0.063 Uiso 1 1 calc R . . N9 N 0.4351(3) 0.1746(2) 0.39669(13) 0.0480(4) Uani 1 1 d . . . C10 C 0.2334(4) 0.1361(3) 0.39701(18) 0.0570(5) Uani 1 1 d . . . H10 H 0.1795 0.0695 0.3481 0.068 Uiso 1 1 calc R . . C11 C 0.1287(4) 0.2141(4) 0.48260(19) 0.0608(6) Uani 1 1 d . . . H11 H -0.0124 0.2099 0.5029 0.073 Uiso 1 1 calc R . . C12 C 0.6071(4) 0.1195(4) 0.3189(2) 0.0675(6) Uani 1 1 d . . . H12A H 0.5584 0.0497 0.2666 0.101 Uiso 0.50 1 calc PR . . H12B H 0.7353 0.0504 0.3542 0.101 Uiso 0.50 1 calc PR . . H12C H 0.6410 0.2219 0.2845 0.101 Uiso 0.50 1 calc PR . . H12D H 0.7314 0.1649 0.3369 0.101 Uiso 0.50 1 calc PR . . H12E H 0.5545 0.1643 0.2493 0.101 Uiso 0.50 1 calc PR . . H12F H 0.6488 -0.0072 0.3190 0.101 Uiso 0.50 1 calc PR . . N13 N -0.2587(3) 0.2639(3) 0.74682(14) 0.0557(4) Uani 1 1 d . . . O14 O -0.0713(3) 0.1726(3) 0.7484(2) 0.0989(7) Uani 1 1 d . . . O15 O -0.3023(4) 0.4063(4) 0.6979(2) 0.1152(10) Uani 1 1 d . . . O16 O -0.4028(3) 0.2128(3) 0.79643(16) 0.0844(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.08224(15) 0.06932(14) 0.04835(11) -0.01577(8) 0.00515(9) -0.02091(10) N1 0.0550(9) 0.0585(11) 0.0445(9) -0.0064(8) 0.0008(7) -0.0154(8) C2 0.0508(11) 0.0615(14) 0.0578(12) -0.0011(10) -0.0022(9) -0.0121(10) N3 0.0619(10) 0.0432(9) 0.0575(10) -0.0024(8) 0.0118(8) -0.0089(8) C4 0.0671(13) 0.0568(13) 0.0476(11) -0.0038(9) -0.0031(10) -0.0201(10) C5 0.0512(11) 0.0602(13) 0.0494(11) -0.0023(9) -0.0034(9) -0.0133(9) C6 0.0881(18) 0.0572(15) 0.096(2) -0.0119(14) 0.0319(16) 0.0010(13) N7 0.0525(9) 0.0658(12) 0.0467(9) -0.0115(8) -0.0020(8) -0.0116(8) C8 0.0509(11) 0.0574(13) 0.0510(11) -0.0057(9) -0.0027(9) -0.0158(9) N9 0.0517(9) 0.0461(9) 0.0456(8) 0.0001(7) 0.0017(7) -0.0104(7) C10 0.0601(12) 0.0648(14) 0.0499(11) -0.0089(10) -0.0059(10) -0.0209(10) C11 0.0471(11) 0.0820(17) 0.0563(12) -0.0105(11) -0.0002(9) -0.0198(11) C12 0.0720(14) 0.0717(16) 0.0583(13) -0.0057(11) 0.0176(12) -0.0154(12) N13 0.0517(10) 0.0717(13) 0.0483(9) -0.0217(9) 0.0020(8) -0.0213(9) O14 0.0583(11) 0.0980(17) 0.139(2) -0.0390(15) 0.0152(12) -0.0102(10) O15 0.111(2) 0.111(2) 0.133(2) 0.0369(19) -0.0426(18) -0.0509(17) O16 0.0693(11) 0.1148(17) 0.0762(12) -0.0082(11) 0.0154(9) -0.0353(11) _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 2.1258(18) . ? Ag1 N7 2.1196(18) . ? N1 C2 1.315(3) . ? N1 C5 1.364(3) . ? C2 N3 1.324(3) . ? N3 C4 1.371(3) . ? N3 C6 1.465(3) . ? C4 C5 1.343(3) . ? N7 C8 1.313(3) . ? N7 C11 1.369(3) . ? C8 N9 1.334(3) . ? N9 C10 1.369(3) . ? N9 C12 1.456(3) . ? C10 C11 1.347(3) . ? N13 O14 1.228(3) . ? N13 O15 1.223(3) . ? N13 O16 1.230(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N7 Ag1 N1 174.17(7) . . ? C2 N1 Ag1 127.05(15) . . ? C2 N1 C5 105.32(18) . . ? C5 N1 Ag1 127.63(15) . . ? N1 C2 N3 111.82(19) . . ? C2 N3 C4 106.97(19) . . ? C2 N3 C6 126.4(2) . . ? C4 N3 C6 126.6(2) . . ? C5 C4 N3 106.08(19) . . ? C4 C5 N1 109.81(19) . . ? C8 N7 Ag1 128.97(15) . . ? C8 N7 C11 105.28(18) . . ? C11 N7 Ag1 125.31(15) . . ? N7 C8 N9 111.76(18) . . ? C8 N9 C10 107.02(18) . . ? C8 N9 C12 126.56(19) . . ? C10 N9 C12 126.42(19) . . ? C11 C10 N9 106.07(19) . . ? C10 C11 N7 109.9(2) . . ? O14 N13 O16 119.6(2) . . ? O15 N13 O14 120.5(2) . . ? O15 N13 O16 119.9(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 N1 C2 N3 -179.86(15) . . . . ? Ag1 N1 C5 C4 -179.96(16) . . . . ? Ag1 N7 C8 N9 172.82(15) . . . . ? Ag1 N7 C11 C10 -173.18(17) . . . . ? N1 Ag1 N7 C8 62.7(7) . . . . ? N1 Ag1 N7 C11 -126.0(6) . . . . ? N1 C2 N3 C4 -0.2(3) . . . . ? N1 C2 N3 C6 179.5(2) . . . . ? C2 N1 C5 C4 0.2(3) . . . . ? C2 N3 C4 C5 0.3(3) . . . . ? N3 C4 C5 N1 -0.3(3) . . . . ? C5 N1 C2 N3 0.0(3) . . . . ? C6 N3 C4 C5 -179.4(2) . . . . ? N7 Ag1 N1 C2 92.7(6) . . . . ? N7 Ag1 N1 C5 -87.1(6) . . . . ? N7 C8 N9 C10 -0.1(3) . . . . ? N7 C8 N9 C12 179.6(2) . . . . ? C8 N7 C11 C10 -0.2(3) . . . . ? C8 N9 C10 C11 0.0(3) . . . . ? N9 C10 C11 N7 0.1(3) . . . . ? C11 N7 C8 N9 0.2(3) . . . . ? C12 N9 C10 C11 -179.7(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 953609' ####################################################################### # # 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_kb2008 _audit_creation_date 2013-05-23 _audit_creation_method ; Olex2 1.2-beta (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _chemical_name_common ; bis(N-butylimidazole)silver nitrate ; _chemical_name_systematic ; bis(N-butylimidazole)silver nitrate ; _chemical_formula_moiety 'C14 H24 Ag N4, N O3' _chemical_formula_sum 'C14 H24 Ag N5 O3' _chemical_formula_weight 418.25 _chemical_melting_point ? _chemical_oxdiff_formula 'Ag C14 H20 N5 O3' 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 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 16.4340(13) _cell_length_b 7.8736(7) _cell_length_c 13.8845(13) _cell_angle_alpha 90.00 _cell_angle_beta 106.748(9) _cell_angle_gamma 90.00 _cell_volume 1720.4(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4123 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 29.007 _cell_measurement_theta_min 3.097 _exptl_absorpt_coefficient_mu 1.193 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.866 _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 1.615 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 856 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_unetI/netI 0.0284 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7334 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 29.24 _diffrn_reflns_theta_min 2.89 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 15.9631 _diffrn_measured_fraction_theta_full 0.9981 _diffrn_measured_fraction_theta_max 0.8467 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -78.00 -5.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -17.1513 -57.0000 90.0000 73 #__ type_ start__ end____ width___ exp.time_ 2 omega -11.00 21.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -17.1513 -99.0000 -120.0000 32 #__ type_ start__ end____ width___ exp.time_ 3 omega -64.00 -35.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -17.1513 -178.0000 -150.0000 29 #__ type_ start__ end____ width___ exp.time_ 4 omega -44.00 43.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -17.1513 19.0000 -90.0000 87 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0063258000 _diffrn_orient_matrix_UB_12 0.0781839000 _diffrn_orient_matrix_UB_13 0.0220947000 _diffrn_orient_matrix_UB_21 0.0323618000 _diffrn_orient_matrix_UB_22 0.0379382000 _diffrn_orient_matrix_UB_23 -0.0174822000 _diffrn_orient_matrix_UB_31 -0.0308325000 _diffrn_orient_matrix_UB_32 0.0236855000 _diffrn_orient_matrix_UB_33 -0.0452191000 _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 3567 _reflns_number_total 3931 _reflns_odcompleteness_completeness 99.81 _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 ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.542 _refine_diff_density_min -0.507 _refine_diff_density_rms 0.068 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 3931 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0218 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0170P)^2^+0.9726P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.0511 _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), C7(H7A,H7B), C8(H8A,H8B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14) 2.c Idealised Me refined as rotating group: C9(H9A,H9B,H9C), C18(H18A,H18B,H18C) ; _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 0.742904(8) 0.728016(18) 0.726390(10) 0.01592(5) Uani 1 1 d . . . N1 N 0.61903(9) 0.6410(2) 0.72336(11) 0.0155(3) Uani 1 1 d . . . C2 C 0.58983(11) 0.6362(2) 0.80289(13) 0.0153(4) Uani 1 1 d . . . H2 H 0.6213 0.6671 0.8675 0.018 Uiso 1 1 calc R . . N3 N 0.50902(9) 0.58088(19) 0.77828(11) 0.0139(3) Uani 1 1 d . . . C4 C 0.48431(11) 0.5481(2) 0.67654(13) 0.0156(4) Uani 1 1 d . . . H4 H 0.4317 0.5079 0.6382 0.019 Uiso 1 1 calc R . . C5 C 0.55245(11) 0.5863(2) 0.64359(13) 0.0162(4) Uani 1 1 d . . . H5 H 0.5540 0.5771 0.5774 0.019 Uiso 1 1 calc R . . C6 C 0.45695(11) 0.5638(2) 0.84788(13) 0.0174(4) Uani 1 1 d . . . H6A H 0.4861 0.6180 0.9112 0.021 Uiso 1 1 calc R . . H6B H 0.4508 0.4443 0.8611 0.021 Uiso 1 1 calc R . . C7 C 0.36935(11) 0.6425(3) 0.80711(14) 0.0190(4) Uani 1 1 d . . . H7A H 0.3396 0.5871 0.7444 0.023 Uiso 1 1 calc R . . H7B H 0.3753 0.7618 0.7930 0.023 Uiso 1 1 calc R . . C8 C 0.31675(12) 0.6256(3) 0.88164(14) 0.0228(4) Uani 1 1 d . . . H8A H 0.2588 0.6606 0.8485 0.027 Uiso 1 1 calc R . . H8B H 0.3154 0.5071 0.9001 0.027 Uiso 1 1 calc R . . C9 C 0.35074(14) 0.7301(3) 0.97654(16) 0.0251(4) Uani 1 1 d . . . H9A H 0.3569 0.8463 0.9588 0.038 Uiso 1 1 calc R . . H9B H 0.4050 0.6863 1.0145 0.038 Uiso 1 1 calc R . . H9C H 0.3118 0.7240 1.0164 0.038 Uiso 1 1 calc R . . N10 N 0.87160(9) 0.8137(2) 0.77138(11) 0.0151(3) Uani 1 1 d . . . C11 C 0.92814(11) 0.7846(2) 0.72205(14) 0.0156(4) Uani 1 1 d . . . H11 H 0.9151 0.7397 0.6574 0.019 Uiso 1 1 calc R . . N12 N 1.00702(9) 0.8285(2) 0.77728(11) 0.0146(3) Uani 1 1 d . . . C13 C 1.00045(11) 0.8890(2) 0.86756(13) 0.0168(4) Uani 1 1 d . . . H13 H 1.0446 0.9287 0.9211 0.020 Uiso 1 1 calc R . . C14 C 0.91660(11) 0.8796(2) 0.86337(13) 0.0164(4) Uani 1 1 d . . . H14 H 0.8935 0.9123 0.9143 0.020 Uiso 1 1 calc R . . C15 C 1.08588(11) 0.8108(2) 0.74722(14) 0.0174(4) Uani 1 1 d . . . H15A H 1.1008 0.6915 0.7479 0.021 Uiso 1 1 calc R . . H15B H 1.1318 0.8689 0.7958 0.021 Uiso 1 1 calc R . . C16 C 1.07669(11) 0.8831(2) 0.64351(14) 0.0178(4) Uani 1 1 d . . . H16A H 1.0572 0.9997 0.6413 0.021 Uiso 1 1 calc R . . H16B H 1.0339 0.8188 0.5942 0.021 Uiso 1 1 calc R . . C17 C 1.16020(12) 0.8780(3) 0.61552(15) 0.0215(4) Uani 1 1 d . . . H17A H 1.2052 0.9266 0.6699 0.026 Uiso 1 1 calc R . . H17B H 1.1750 0.7609 0.6070 0.026 Uiso 1 1 calc R . . C18 C 1.15359(13) 0.9759(3) 0.51897(16) 0.0282(5) Uani 1 1 d . . . H18A H 1.1125 0.9222 0.4639 0.042 Uiso 1 1 calc R . . H18B H 1.2079 0.9768 0.5061 0.042 Uiso 1 1 calc R . . H18C H 1.1362 1.0905 0.5260 0.042 Uiso 1 1 calc R . . N19 N 0.25765(9) 0.3903(2) 0.50398(11) 0.0152(3) Uani 1 1 d . . . O20 O 0.27056(8) 0.42653(18) 0.59441(9) 0.0210(3) Uani 1 1 d . . . O21 O 0.18960(8) 0.43393(18) 0.44084(10) 0.0256(3) Uani 1 1 d . . . O22 O 0.31323(9) 0.31014(18) 0.47604(10) 0.0224(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.00974(7) 0.01748(8) 0.02012(8) 0.00194(5) 0.00361(5) -0.00071(5) N1 0.0118(7) 0.0171(8) 0.0173(7) -0.0006(6) 0.0039(6) -0.0005(6) C2 0.0126(8) 0.0150(9) 0.0170(8) -0.0010(7) 0.0019(7) -0.0009(7) N3 0.0106(7) 0.0145(7) 0.0163(7) -0.0004(6) 0.0035(6) -0.0004(6) C4 0.0125(8) 0.0153(9) 0.0172(8) -0.0012(7) 0.0013(7) -0.0001(7) C5 0.0153(9) 0.0162(9) 0.0162(8) -0.0020(7) 0.0032(7) 0.0010(7) C6 0.0160(9) 0.0189(9) 0.0189(9) 0.0004(7) 0.0075(7) -0.0021(8) C7 0.0146(9) 0.0226(10) 0.0203(9) -0.0042(8) 0.0057(7) -0.0001(8) C8 0.0167(9) 0.0274(11) 0.0267(10) -0.0071(9) 0.0097(8) -0.0037(8) C9 0.0250(10) 0.0246(11) 0.0307(11) -0.0084(9) 0.0157(9) -0.0050(9) N10 0.0114(7) 0.0171(8) 0.0166(7) 0.0009(6) 0.0034(6) -0.0020(6) C11 0.0132(8) 0.0181(9) 0.0149(8) -0.0005(7) 0.0032(7) -0.0020(7) N12 0.0107(7) 0.0161(7) 0.0167(7) -0.0002(6) 0.0034(6) -0.0015(6) C13 0.0164(9) 0.0179(9) 0.0149(8) -0.0010(7) 0.0024(7) -0.0032(8) C14 0.0179(9) 0.0171(9) 0.0151(8) -0.0010(7) 0.0063(7) -0.0011(8) C15 0.0102(8) 0.0206(10) 0.0221(9) -0.0043(8) 0.0056(7) -0.0009(8) C16 0.0137(8) 0.0194(9) 0.0219(9) -0.0025(8) 0.0077(7) -0.0022(8) C17 0.0185(9) 0.0203(10) 0.0291(10) -0.0037(8) 0.0123(8) -0.0017(8) C18 0.0280(11) 0.0269(11) 0.0370(12) 0.0008(9) 0.0209(10) 0.0027(9) N19 0.0137(7) 0.0145(8) 0.0161(7) 0.0007(6) 0.0024(6) -0.0027(6) O20 0.0207(7) 0.0285(8) 0.0134(6) -0.0024(6) 0.0045(5) -0.0006(6) O21 0.0173(7) 0.0273(8) 0.0239(7) 0.0020(6) -0.0071(6) 0.0023(6) O22 0.0223(7) 0.0263(7) 0.0214(7) 0.0000(6) 0.0108(6) 0.0056(6) _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 2.1369(15) . ? Ag1 N10 2.1346(15) . ? N1 C2 1.325(2) . ? N1 C5 1.382(2) . ? C2 N3 1.345(2) . ? N3 C4 1.377(2) . ? N3 C6 1.470(2) . ? C4 C5 1.360(3) . ? C6 C7 1.519(2) . ? C7 C8 1.533(3) . ? C8 C9 1.517(3) . ? N10 C11 1.323(2) . ? N10 C14 1.380(2) . ? C11 N12 1.347(2) . ? N12 C13 1.374(2) . ? N12 C15 1.478(2) . ? C13 C14 1.364(2) . ? C15 C16 1.515(3) . ? C16 C17 1.531(2) . ? C17 C18 1.523(3) . ? N19 O20 1.2448(19) . ? N19 O21 1.2540(19) . ? N19 O22 1.2597(19) . ? 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 N10 Ag1 N1 164.80(6) . . ? C2 N1 Ag1 124.36(12) . . ? C2 N1 C5 105.40(15) . . ? C5 N1 Ag1 130.19(12) . . ? N1 C2 N3 111.45(15) . . ? C2 N3 C4 107.41(15) . . ? C2 N3 C6 125.58(15) . . ? C4 N3 C6 127.00(15) . . ? C5 C4 N3 105.99(15) . . ? C4 C5 N1 109.75(16) . . ? N3 C6 C7 112.74(15) . . ? C6 C7 C8 111.79(16) . . ? C9 C8 C7 113.65(16) . . ? C11 N10 Ag1 125.33(12) . . ? C11 N10 C14 105.97(15) . . ? C14 N10 Ag1 127.68(12) . . ? N10 C11 N12 111.42(16) . . ? C11 N12 C13 107.01(15) . . ? C11 N12 C15 126.39(15) . . ? C13 N12 C15 126.58(15) . . ? C14 C13 N12 106.62(15) . . ? C13 C14 N10 108.98(16) . . ? N12 C15 C16 112.18(15) . . ? C15 C16 C17 112.36(15) . . ? C18 C17 C16 111.63(16) . . ? O20 N19 O21 120.05(15) . . ? O20 N19 O22 119.84(15) . . ? O21 N19 O22 120.12(15) . . ? 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 N1 C2 N3 178.01(11) . . . . ? Ag1 N1 C5 C4 -177.97(13) . . . . ? Ag1 N10 C11 N12 -169.21(12) . . . . ? Ag1 N10 C14 C13 168.83(13) . . . . ? N1 Ag1 N10 C11 149.0(2) . . . . ? N1 Ag1 N10 C14 -17.8(3) . . . . ? N1 C2 N3 C4 -0.1(2) . . . . ? N1 C2 N3 C6 -178.62(16) . . . . ? C2 N1 C5 C4 -0.5(2) . . . . ? C2 N3 C4 C5 -0.2(2) . . . . ? C2 N3 C6 C7 131.64(18) . . . . ? N3 C4 C5 N1 0.5(2) . . . . ? N3 C6 C7 C8 -179.11(15) . . . . ? C4 N3 C6 C7 -46.6(2) . . . . ? C5 N1 C2 N3 0.4(2) . . . . ? C6 N3 C4 C5 178.27(17) . . . . ? C6 C7 C8 C9 67.6(2) . . . . ? N10 Ag1 N1 C2 9.8(3) . . . . ? N10 Ag1 N1 C5 -173.19(19) . . . . ? N10 C11 N12 C13 0.1(2) . . . . ? N10 C11 N12 C15 178.76(17) . . . . ? C11 N10 C14 C13 0.0(2) . . . . ? C11 N12 C13 C14 -0.1(2) . . . . ? C11 N12 C15 C16 49.4(2) . . . . ? N12 C13 C14 N10 0.0(2) . . . . ? N12 C15 C16 C17 175.39(15) . . . . ? C13 N12 C15 C16 -132.16(19) . . . . ? C14 N10 C11 N12 -0.1(2) . . . . ? C15 N12 C13 C14 -178.74(17) . . . . ? C15 C16 C17 C18 -170.94(17) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 953610' ####################################################################### # # 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_nrb66 _audit_creation_date 2013-07-29 _audit_creation_method ; Olex2 1.2-beta (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _chemical_name_common ; bis(N-dodecylimidazole)silver nitrate dihydrate ; _chemical_name_systematic ; bis(N-dodecylimidazole)silver nitrate dihydrate ; _chemical_formula_moiety 'C30 H56 Ag N4, N O3, 2 (H2 O)' _chemical_formula_sum 'C30 H60 Ag N5 O5' _chemical_formula_weight 678.70 _chemical_melting_point ? 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 triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 4.5579(4) _cell_length_b 8.2220(5) _cell_length_c 23.099(2) _cell_angle_alpha 89.274(7) _cell_angle_beta 87.415(7) _cell_angle_gamma 78.188(6) _cell_volume 846.45(12) _cell_formula_units_Z 1 _cell_measurement_reflns_used 2084 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 29.146 _cell_measurement_theta_min 3.075 _exptl_absorpt_coefficient_mu 0.638 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.929 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 362 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.02 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_unetI/netI 0.0914 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 6872 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 29.21 _diffrn_reflns_theta_min 3.08 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 15.9631 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.839 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -86.00 -50.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.1513 -178.0000 60.0000 36 #__ type_ start__ end____ width___ exp.time_ 2 omega -17.00 25.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.1513 -99.0000 120.0000 42 #__ type_ start__ end____ width___ exp.time_ 3 omega -19.00 92.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 18.8701 19.0000 30.0000 111 #__ type_ start__ end____ width___ exp.time_ 4 omega 24.00 52.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 18.8701 -99.0000 0.0000 28 #__ type_ start__ end____ width___ exp.time_ 5 omega 9.00 84.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 18.8701 57.0000 90.0000 75 #__ type_ start__ end____ width___ exp.time_ 6 omega -51.00 47.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 18.8701 -77.0000 -120.0000 98 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1199890000 _diffrn_orient_matrix_UB_12 0.0156757000 _diffrn_orient_matrix_UB_13 0.0161395000 _diffrn_orient_matrix_UB_21 0.0601250000 _diffrn_orient_matrix_UB_22 0.0343139000 _diffrn_orient_matrix_UB_23 -0.0250643000 _diffrn_orient_matrix_UB_31 -0.0855081000 _diffrn_orient_matrix_UB_32 0.0796524000 _diffrn_orient_matrix_UB_33 0.0075036000 _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 3176 _reflns_number_total 3850 _reflns_odcompleteness_completeness 99.83 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _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 ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.511 _refine_diff_density_min -0.915 _refine_diff_density_rms 0.100 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 214 _refine_ls_number_reflns 3850 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0526 _refine_ls_restrained_S_all 1.021 _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^)+(0.0278P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0840 _refine_ls_wR_factor_ref 0.0937 _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: N18(0.5) O19(0.5) O20(0.5) O21(0.5) O1W(0.5) O2W(0.5) 3.a Secondary CH2 refined with riding coordinates: C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A, H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B) 3.b Me refined with riding coordinates: C17(H17A,H17B,H17C) 3.c Aromatic/amide H refined with riding coordinates: C2(H2), C4(H4), C5(H5) ; _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 0.0000 1.0000 0.03075(13) Uani 1 2 d S . . N1 N 0.3361(5) -0.0843(3) 0.93579(10) 0.0194(6) Uani 1 1 d . . . N3 N 0.6784(5) -0.0928(3) 0.86459(10) 0.0150(5) Uani 1 1 d . . . C2 C 0.4845(6) 0.0043(4) 0.90176(13) 0.0197(7) Uani 1 1 d . . . H2 H 0.4585 0.1193 0.9033 0.024 Uiso 1 1 calc R . . C4 C 0.6503(6) -0.2536(3) 0.87545(13) 0.0204(7) Uani 1 1 d . . . H4 H 0.7543 -0.3484 0.8564 0.025 Uiso 1 1 calc R . . C5 C 0.4408(7) -0.2469(4) 0.91949(13) 0.0239(7) Uani 1 1 d . . . H5 H 0.3776 -0.3382 0.9361 0.029 Uiso 1 1 calc R . . C6 C 0.8570(6) -0.0369(4) 0.81716(12) 0.0189(6) Uani 1 1 d . . . H6A H 1.0350 -0.1220 0.8089 0.023 Uiso 1 1 calc R . . H6B H 0.9210 0.0628 0.8288 0.023 Uiso 1 1 calc R . . C7 C 0.6790(6) -0.0008(3) 0.76249(12) 0.0170(6) Uani 1 1 d . . . H7A H 0.5037 0.0860 0.7708 0.020 Uiso 1 1 calc R . . H7B H 0.6097 -0.0998 0.7518 0.020 Uiso 1 1 calc R . . C8 C 0.8598(6) 0.0534(3) 0.71125(12) 0.0169(6) Uani 1 1 d . . . H8A H 0.9372 0.1494 0.7225 0.020 Uiso 1 1 calc R . . H8B H 1.0299 -0.0355 0.7017 0.020 Uiso 1 1 calc R . . C9 C 0.6769(6) 0.0972(3) 0.65765(12) 0.0176(6) Uani 1 1 d . . . H9A H 0.5075 0.1865 0.6673 0.021 Uiso 1 1 calc R . . H9B H 0.5981 0.0014 0.6468 0.021 Uiso 1 1 calc R . . C10 C 0.8535(6) 0.1504(3) 0.60581(12) 0.0165(6) Uani 1 1 d . . . H10A H 1.0208 0.0603 0.5958 0.020 Uiso 1 1 calc R . . H10B H 0.9355 0.2449 0.6169 0.020 Uiso 1 1 calc R . . C11 C 0.6692(6) 0.1973(4) 0.55242(12) 0.0171(6) Uani 1 1 d . . . H11A H 0.5875 0.1029 0.5413 0.021 Uiso 1 1 calc R . . H11B H 0.5019 0.2874 0.5625 0.021 Uiso 1 1 calc R . . C12 C 0.8463(6) 0.2506(3) 0.50075(12) 0.0173(6) Uani 1 1 d . . . H12A H 1.0125 0.1601 0.4906 0.021 Uiso 1 1 calc R . . H12B H 0.9300 0.3442 0.5121 0.021 Uiso 1 1 calc R . . C13 C 0.6644(6) 0.2997(3) 0.44723(12) 0.0170(6) Uani 1 1 d . . . H13A H 0.4984 0.3905 0.4573 0.020 Uiso 1 1 calc R . . H13B H 0.5805 0.2062 0.4358 0.020 Uiso 1 1 calc R . . C14 C 0.8444(6) 0.3526(3) 0.39565(12) 0.0173(6) Uani 1 1 d . . . H14A H 0.9277 0.4462 0.4071 0.021 Uiso 1 1 calc R . . H14B H 1.0109 0.2619 0.3858 0.021 Uiso 1 1 calc R . . C15 C 0.6651(6) 0.4012(3) 0.34178(12) 0.0175(6) Uani 1 1 d . . . H15A H 0.5872 0.3067 0.3294 0.021 Uiso 1 1 calc R . . H15B H 0.4952 0.4899 0.3517 0.021 Uiso 1 1 calc R . . C16 C 0.8475(6) 0.4585(4) 0.29156(12) 0.0200(7) Uani 1 1 d . . . H16A H 1.0183 0.3702 0.2818 0.024 Uiso 1 1 calc R . . H16B H 0.9239 0.5537 0.3039 0.024 Uiso 1 1 calc R . . C17 C 0.6679(6) 0.5058(4) 0.23738(13) 0.0238(7) Uani 1 1 d . . . H17A H 0.7945 0.5407 0.2074 0.036 Uiso 1 1 calc R . . H17B H 0.5009 0.5951 0.2464 0.036 Uiso 1 1 calc R . . H17C H 0.5955 0.4115 0.2243 0.036 Uiso 1 1 calc R . . N18 N 0.0868(10) 0.6389(6) 0.0817(2) 0.0191(11) Uani 0.50 1 d P A 1 O19 O 0.2810(9) 0.6499(5) 0.04286(19) 0.0299(11) Uani 0.50 1 d P A 1 O20 O -0.1472(10) 0.5931(6) 0.0671(2) 0.0310(11) Uani 0.50 1 d P A 1 O21 O 0.1245(19) 0.6764(17) 0.1318(6) 0.040(3) Uani 0.50 1 d P A 1 O1W O -0.0835(10) 0.6328(6) 0.0292(2) 0.0314(11) Uani 0.50 1 d P B 2 O2W O 0.2459(18) 0.6516(15) 0.1279(6) 0.030(2) Uani 0.50 1 d P C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.01909(19) 0.0506(3) 0.0199(2) -0.00850(16) -0.00068(14) -0.00045(16) N1 0.0142(12) 0.0265(15) 0.0187(14) -0.0027(11) 0.0006(10) -0.0071(11) N3 0.0120(11) 0.0161(13) 0.0174(13) 0.0012(10) -0.0016(10) -0.0037(10) C2 0.0167(15) 0.0191(16) 0.0235(18) -0.0023(13) -0.0053(13) -0.0029(12) C4 0.0247(16) 0.0136(16) 0.0219(17) -0.0021(12) -0.0007(13) -0.0011(12) C5 0.0249(16) 0.0245(18) 0.0241(18) -0.0001(13) 0.0021(13) -0.0102(13) C6 0.0144(14) 0.0222(16) 0.0211(17) 0.0034(12) -0.0007(12) -0.0060(12) C7 0.0143(14) 0.0182(15) 0.0193(16) 0.0010(12) -0.0016(12) -0.0049(12) C8 0.0124(13) 0.0188(16) 0.0199(16) -0.0002(12) -0.0012(12) -0.0039(11) C9 0.0144(14) 0.0179(16) 0.0204(17) 0.0012(12) -0.0016(12) -0.0031(12) C10 0.0118(13) 0.0151(15) 0.0227(17) 0.0012(12) 0.0004(12) -0.0030(11) C11 0.0126(14) 0.0194(16) 0.0194(16) -0.0004(12) 0.0000(12) -0.0034(11) C12 0.0130(14) 0.0184(15) 0.0206(17) -0.0011(12) -0.0018(12) -0.0032(12) C13 0.0135(14) 0.0175(15) 0.0198(16) 0.0001(12) -0.0009(12) -0.0028(12) C14 0.0143(14) 0.0173(16) 0.0206(17) -0.0037(12) -0.0023(12) -0.0034(12) C15 0.0149(14) 0.0174(15) 0.0200(16) -0.0024(12) -0.0019(12) -0.0025(12) C16 0.0170(14) 0.0219(16) 0.0209(17) -0.0003(12) -0.0012(12) -0.0033(12) C17 0.0247(16) 0.0255(17) 0.0203(17) -0.0012(13) -0.0016(13) -0.0024(13) N18 0.015(3) 0.010(3) 0.030(3) 0.003(2) 0.006(2) 0.002(2) O19 0.023(2) 0.039(3) 0.029(3) 0.001(2) 0.006(2) -0.012(2) O20 0.018(2) 0.026(3) 0.051(4) -0.011(2) 0.002(2) -0.008(2) O21 0.064(7) 0.032(5) 0.023(4) -0.001(3) -0.002(6) -0.006(5) O1W 0.029(3) 0.032(3) 0.035(3) -0.002(2) -0.004(2) -0.009(2) O2W 0.046(5) 0.013(4) 0.032(4) -0.004(3) -0.013(5) -0.006(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 Ag1 N1 2.101(2) . ? Ag1 N1 2.101(2) 2_557 ? N1 C2 1.321(4) . ? N1 C5 1.375(4) . ? N3 C2 1.347(3) . ? N3 C4 1.373(3) . ? N3 C6 1.461(3) . ? C4 C5 1.357(4) . ? C6 C7 1.525(4) . ? C7 C8 1.526(4) . ? C8 C9 1.522(4) . ? C9 C10 1.522(4) . ? C10 C11 1.525(4) . ? C11 C12 1.521(4) . ? C12 C13 1.524(4) . ? C13 C14 1.525(4) . ? C14 C15 1.524(4) . ? C15 C16 1.522(4) . ? C16 C17 1.529(4) . ? N18 O19 1.247(6) . ? N18 O20 1.261(7) . ? N18 O21 1.232(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ag1 N1 180.00(18) 2_557 . ? C2 N1 Ag1 128.4(2) . . ? C2 N1 C5 105.6(2) . . ? C5 N1 Ag1 126.0(2) . . ? C2 N3 C4 106.8(2) . . ? C2 N3 C6 126.6(2) . . ? C4 N3 C6 126.2(2) . . ? N1 C2 N3 111.6(3) . . ? C5 C4 N3 106.5(3) . . ? C4 C5 N1 109.6(3) . . ? N3 C6 C7 111.5(2) . . ? C6 C7 C8 113.3(2) . . ? C9 C8 C7 113.1(2) . . ? C8 C9 C10 114.0(2) . . ? C9 C10 C11 114.0(2) . . ? C12 C11 C10 113.9(2) . . ? C11 C12 C13 114.5(2) . . ? C12 C13 C14 114.1(2) . . ? C15 C14 C13 114.5(2) . . ? C16 C15 C14 113.5(2) . . ? C15 C16 C17 113.4(2) . . ? O19 N18 O20 117.7(6) . . ? O21 N18 O19 119.8(7) . . ? O21 N18 O20 122.5(8) . . ? 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 N1 C2 N3 -178.26(17) . . . . ? Ag1 N1 C5 C4 177.94(19) . . . . ? N1 Ag1 N1 C2 140(38) 2_557 . . . ? N1 Ag1 N1 C5 -38(38) 2_557 . . . ? N3 C4 C5 N1 0.6(3) . . . . ? N3 C6 C7 C8 -178.4(2) . . . . ? C2 N1 C5 C4 -0.4(3) . . . . ? C2 N3 C4 C5 -0.6(3) . . . . ? C2 N3 C6 C7 -84.7(3) . . . . ? C4 N3 C2 N1 0.4(3) . . . . ? C4 N3 C6 C7 87.2(3) . . . . ? C5 N1 C2 N3 0.0(3) . . . . ? C6 N3 C2 N1 173.5(2) . . . . ? C6 N3 C4 C5 -173.7(3) . . . . ? C6 C7 C8 C9 -177.3(2) . . . . ? C7 C8 C9 C10 -179.6(2) . . . . ? C8 C9 C10 C11 -178.9(2) . . . . ? C9 C10 C11 C12 179.9(2) . . . . ? C10 C11 C12 C13 -179.4(2) . . . . ? C11 C12 C13 C14 -179.9(2) . . . . ? C12 C13 C14 C15 179.8(2) . . . . ? C13 C14 C15 C16 178.3(2) . . . . ? C14 C15 C16 C17 179.5(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 953611'