# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_p _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H6 Ag N3 O4' _chemical_formula_weight 292.01 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.047(2) _cell_length_b 8.016(2) _cell_length_c 12.733(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.380(4) _cell_angle_gamma 90.00 _cell_volume 817.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 2.456 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7095 _exptl_absorpt_correction_T_max 0.7912 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3518 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1428 _reflns_number_gt 1316 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0201P)^2^+1.6438P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1428 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0604 _refine_ls_wR_factor_gt 0.0592 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag 0.46034(4) 0.73247(5) 0.45525(2) 0.04744(14) Uani 1 1 d . . . C1 C 0.4353(4) 0.8189(5) 0.6997(3) 0.0378(9) Uani 1 1 d . . . H1 H 0.3193 0.8139 0.6936 0.045 Uiso 1 1 calc R . . C2 C 0.6835(4) 0.8289(5) 0.7662(3) 0.0347(8) Uani 1 1 d . . . H2 H 0.7787 0.8318 0.8136 0.042 Uiso 1 1 calc R . . C3 C 0.9141(4) 1.0187(4) 0.6163(2) 0.0264(7) Uani 1 1 d . . . C4 C 0.8259(4) 0.8480(4) 0.5980(2) 0.0252(7) Uani 1 1 d . . . H4 H 0.7815 0.8435 0.5237 0.030 Uiso 1 1 calc R . . C5 C 0.9442(4) 0.7031(4) 0.6176(3) 0.0300(7) Uani 1 1 d . . . H5A H 0.9888 0.7044 0.6911 0.036 Uiso 1 1 calc R . . H5B H 1.0370 0.7177 0.5750 0.036 Uiso 1 1 calc R . . C6 C 0.8645(4) 0.5340(4) 0.5926(3) 0.0274(7) Uani 1 1 d . . . N1 N 0.5228(3) 0.8276(4) 0.6179(2) 0.0323(7) Uani 1 1 d . . . N2 N 0.5288(3) 0.8180(4) 0.7932(2) 0.0360(7) Uani 1 1 d . . . N3 N 0.6830(3) 0.8348(3) 0.66201(19) 0.0239(6) Uani 1 1 d . . . O1 O 0.8156(3) 1.1400(3) 0.6238(2) 0.0377(6) Uani 1 1 d . . . O2 O 1.0667(3) 1.0266(3) 0.61957(19) 0.0353(6) Uani 1 1 d . . . O3 O 0.9507(3) 0.4141(3) 0.6350(2) 0.0423(6) Uani 1 1 d . . . H3 H 0.8971 0.3272 0.6279 0.064 Uiso 1 1 calc R . . O4 O 0.7345(3) 0.5171(3) 0.5361(2) 0.0466(7) 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 0.03137(19) 0.0880(3) 0.02259(16) -0.01137(14) 0.00083(11) -0.00563(15) C1 0.0202(17) 0.069(3) 0.0251(18) -0.0024(17) 0.0035(14) -0.0045(16) C2 0.0228(18) 0.056(2) 0.0248(17) 0.0033(16) -0.0010(14) -0.0043(16) C3 0.0288(18) 0.0258(17) 0.0249(16) 0.0011(13) 0.0039(13) -0.0072(14) C4 0.0231(17) 0.0275(17) 0.0252(16) -0.0015(13) 0.0036(13) -0.0017(13) C5 0.0261(18) 0.0303(18) 0.0336(18) -0.0017(14) 0.0028(14) -0.0021(14) C6 0.0254(17) 0.0262(17) 0.0315(17) -0.0016(14) 0.0071(14) 0.0005(13) N1 0.0205(15) 0.0536(19) 0.0226(14) -0.0032(13) 0.0002(11) -0.0032(13) N2 0.0250(16) 0.062(2) 0.0213(14) 0.0011(13) 0.0033(12) -0.0053(14) N3 0.0184(13) 0.0308(15) 0.0224(13) 0.0004(11) 0.0014(10) -0.0036(11) O1 0.0260(13) 0.0242(12) 0.0621(17) 0.0014(11) 0.0002(12) -0.0013(10) O2 0.0263(13) 0.0328(13) 0.0471(15) -0.0012(11) 0.0047(11) -0.0037(10) O3 0.0379(15) 0.0243(12) 0.0617(17) 0.0007(12) -0.0119(12) -0.0024(11) O4 0.0398(15) 0.0310(14) 0.0652(18) 0.0052(13) -0.0145(13) -0.0021(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 2.220(3) . ? Ag1 N2 2.223(3) 4_575 ? Ag1 O4 2.550(3) 3_666 ? Ag1 O1 2.563(2) 3_676 ? C1 N1 1.312(4) . ? C1 N2 1.347(4) . ? C1 H1 0.9300 . ? C2 N2 1.324(4) . ? C2 N3 1.328(4) . ? C2 H2 0.9300 . ? C3 O2 1.226(4) . ? C3 O1 1.264(4) . ? C3 C4 1.549(4) . ? C4 N3 1.474(4) . ? C4 C5 1.508(5) . ? C4 H4 0.9800 . ? C5 C6 1.521(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O4 1.220(4) . ? C6 O3 1.275(4) . ? N1 N3 1.358(4) . ? N2 Ag1 2.223(3) 4_576 ? O1 Ag1 2.563(2) 3_676 ? O3 H3 0.8200 . ? O4 Ag1 2.550(3) 3_666 ? 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 N2 151.01(11) . 4_575 ? N1 Ag1 O4 108.38(10) . 3_666 ? N2 Ag1 O4 95.98(11) 4_575 3_666 ? N1 Ag1 O1 109.96(10) . 3_676 ? N2 Ag1 O1 89.37(10) 4_575 3_676 ? O4 Ag1 O1 79.43(8) 3_666 3_676 ? N1 C1 N2 113.8(3) . . ? N1 C1 H1 123.1 . . ? N2 C1 H1 123.1 . . ? N2 C2 N3 110.3(3) . . ? N2 C2 H2 124.9 . . ? N3 C2 H2 124.9 . . ? O2 C3 O1 126.2(3) . . ? O2 C3 C4 119.6(3) . . ? O1 C3 C4 114.2(3) . . ? N3 C4 C5 111.5(3) . . ? N3 C4 C3 110.5(3) . . ? C5 C4 C3 112.5(3) . . ? N3 C4 H4 107.4 . . ? C5 C4 H4 107.4 . . ? C3 C4 H4 107.4 . . ? C4 C5 C6 113.9(3) . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? O4 C6 O3 124.7(3) . . ? O4 C6 C5 122.9(3) . . ? O3 C6 C5 112.4(3) . . ? C1 N1 N3 103.5(3) . . ? C1 N1 Ag1 129.1(2) . . ? N3 N1 Ag1 121.5(2) . . ? C2 N2 C1 103.4(3) . . ? C2 N2 Ag1 125.0(2) . 4_576 ? C1 N2 Ag1 130.9(2) . 4_576 ? C2 N3 N1 109.0(3) . . ? C2 N3 C4 128.8(3) . . ? N1 N3 C4 122.3(2) . . ? C3 O1 Ag1 143.5(2) . 3_676 ? C6 O3 H3 109.5 . . ? C6 O4 Ag1 123.9(2) . 3_666 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O1 0.82 1.64 2.450(3) 171.0 1_545 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.959 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 972532'