# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof. Kumar Biradha' _publ_contact_author_email kbiradha@yahoo.com _publ_section_title ; Weak Ag---Ag and Ag---Pi Interactions in Templating Regio Selective Single and Double [2+2] Reactions of N,N'-bis(3-(4-pyridyl)acryloyl)-hydrazine in the Solid State ; loop_ _publ_author_name R.Santra K.Banerjee K.Biradha # Attachment '- kbrks.cif' data_PAH _database_code_depnum_ccdc_archive 'CCDC 826880' #TrackingRef '- kbrks.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 N4 O6' _chemical_formula_weight 366.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 3.7791(7) _cell_length_b 12.616(2) _cell_length_c 17.874(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.028(6) _cell_angle_gamma 90.00 _cell_volume 848.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1499 _cell_measurement_theta_min 1.98 _cell_measurement_theta_max 24.99 _exptl_crystal_description needles _exptl_crystal_colour 'Light yellow' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.984 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD APEX2' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9932 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1499 _reflns_number_gt 1058 _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. # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.079 0.000 0.500 93 26 ' ' 2 -0.080 0.500 0.000 93 26 ' ' _platon_squeeze_details ; _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1499 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1443 _refine_ls_wR_factor_gt 0.1265 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.911 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O18 O 0.2739(4) 0.83486(11) 1.02758(7) 0.0479(5) Uani 1 1 d . . . N11 N 0.5366(5) 0.57243(14) 0.68432(10) 0.0438(5) Uani 1 1 d . . . N12 N 0.0337(4) 0.97633(12) 0.96658(8) 0.0342(4) Uani 1 1 d . . . H12 H -0.0238 1.0076 0.9245 0.041 Uiso 1 1 calc R . . C11 C 0.3828(6) 0.66766(18) 0.68200(11) 0.0430(6) Uani 1 1 d . . . H11 H 0.3002 0.6946 0.6353 0.052 Uiso 1 1 calc R . . C12 C 0.3383(5) 0.72891(17) 0.74465(11) 0.0375(5) Uani 1 1 d . . . H12A H 0.2329 0.7954 0.7396 0.045 Uiso 1 1 calc R . . C13 C 0.4533(5) 0.68958(15) 0.81531(11) 0.0318(5) Uani 1 1 d . . . C14 C 0.6160(5) 0.59116(16) 0.81764(11) 0.0389(5) Uani 1 1 d . . . H14 H 0.7017 0.5621 0.8635 0.047 Uiso 1 1 calc R . . C15 C 0.6511(6) 0.53626(17) 0.75223(12) 0.0441(6) Uani 1 1 d . . . H15 H 0.7608 0.4702 0.7556 0.053 Uiso 1 1 calc R . . C16 C 0.4004(5) 0.74446(16) 0.88598(11) 0.0357(5) Uani 1 1 d . . . H16 H 0.4837 0.7101 0.9301 0.043 Uiso 1 1 calc R . . C17 C 0.2475(5) 0.83721(15) 0.89348(10) 0.0344(5) Uani 1 1 d . . . H17 H 0.1740 0.8761 0.8507 0.041 Uiso 1 1 calc R . . C18 C 0.1898(5) 0.88112(15) 0.96807(10) 0.0310(5) 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 O18 0.0778(11) 0.0393(9) 0.0268(8) 0.0015(6) 0.0045(7) 0.0168(8) N11 0.0516(11) 0.0427(11) 0.0383(11) -0.0127(8) 0.0111(8) -0.0054(9) N12 0.0535(10) 0.0297(9) 0.0204(8) -0.0011(6) 0.0090(7) 0.0040(8) C11 0.0528(13) 0.0476(13) 0.0288(11) -0.0056(9) 0.0054(9) -0.0043(11) C12 0.0439(12) 0.0372(12) 0.0318(11) -0.0039(9) 0.0062(9) 0.0017(9) C13 0.0325(10) 0.0320(11) 0.0312(10) -0.0041(8) 0.0040(8) -0.0015(8) C14 0.0480(13) 0.0353(12) 0.0336(11) -0.0034(9) 0.0038(9) 0.0038(9) C15 0.0488(13) 0.0366(13) 0.0477(14) -0.0117(10) 0.0087(10) 0.0027(10) C16 0.0450(12) 0.0356(11) 0.0263(10) -0.0034(8) 0.0021(8) 0.0022(9) C17 0.0438(12) 0.0334(11) 0.0264(11) 0.0002(8) 0.0062(8) 0.0013(9) C18 0.0394(11) 0.0277(10) 0.0262(10) -0.0013(8) 0.0043(8) -0.0003(8) _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 O18 C18 1.230(2) . ? N11 C15 1.333(3) . ? N11 C11 1.334(3) . ? N12 C18 1.337(3) . ? N12 N12 1.379(3) 3_577 ? C11 C12 1.383(3) . ? C12 C13 1.391(3) . ? C13 C14 1.385(3) . ? C13 C16 1.470(3) . ? C14 C15 1.375(3) . ? C16 C17 1.317(3) . ? C17 C18 1.478(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 C15 N11 C11 116.26(17) . . ? C18 N12 N12 119.10(19) . 3_577 ? N11 C11 C12 124.2(2) . . ? C11 C12 C13 119.0(2) . . ? C14 C13 C12 116.75(18) . . ? C14 C13 C16 119.35(18) . . ? C12 C13 C16 123.86(18) . . ? C15 C14 C13 120.1(2) . . ? N11 C15 C14 123.6(2) . . ? C17 C16 C13 126.88(19) . . ? C16 C17 C18 121.72(18) . . ? O18 C18 N12 121.56(17) . . ? O18 C18 C17 123.70(18) . . ? N12 C18 C17 114.74(16) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.160 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.035 data_1 _database_code_depnum_ccdc_archive 'CCDC 826881' #TrackingRef '- kbrks.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Ag Cl N4 O6' _chemical_formula_weight 501.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5856(12) _cell_length_b 14.516(2) _cell_length_c 17.684(3) _cell_angle_alpha 71.470(5) _cell_angle_beta 80.448(5) _cell_angle_gamma 77.098(5) _cell_volume 1790.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6240 _cell_measurement_theta_min 1.22 _cell_measurement_theta_max 25.00 _exptl_crystal_description Plates _exptl_crystal_colour 'Light yellow' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.861 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 1.319 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.789 _exptl_absorpt_correction_T_max 0.876 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Buuker CCD APEX2' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21068 _diffrn_reflns_av_R_equivalents 0.1558 _diffrn_reflns_av_sigmaI/netI 0.1623 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6240 _reflns_number_gt 2659 _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6240 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1938 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1751 _refine_ls_wR_factor_gt 0.1374 _refine_ls_goodness_of_fit_ref 0.795 _refine_ls_restrained_S_all 0.795 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag 0.15532(12) 1.46261(5) -0.07340(5) 0.0557(3) Uani 1 1 d . . . Ag2 Ag 0.72768(12) -0.02927(5) 0.47593(5) 0.0617(3) Uani 1 1 d . . . Cl2 Cl 0.7263(4) 1.51890(18) -0.14878(16) 0.0566(8) Uani 1 1 d . . . Cl1 Cl 0.6698(4) 2.98653(19) -0.32056(16) 0.0565(7) Uani 1 1 d . . . N21B N -0.2513(12) 2.8140(5) -0.4920(5) 0.055(2) Uani 1 1 d . . . N21A N 0.1820(11) 1.3053(5) -0.0304(5) 0.044(2) Uani 1 1 d . . . N11B N 0.1651(12) 1.6167(5) -0.1098(5) 0.053(2) Uani 1 1 d . . . N11A N 0.7153(11) 0.1271(6) 0.4333(5) 0.053(2) Uani 1 1 d . . . O204 O 0.7611(11) 1.5385(5) -0.0796(4) 0.071(2) Uani 1 1 d . . . O11B O 0.2309(10) 2.1259(4) -0.2104(4) 0.060(2) Uani 1 1 d . . . C23A C 0.2424(12) 1.0983(6) 0.0266(5) 0.036(2) Uani 1 1 d . . . O203 O 0.5954(12) 1.4553(6) -0.1263(5) 0.090(3) Uani 1 1 d . . . C14B C 0.0660(15) 1.7847(7) -0.1863(6) 0.052(3) Uani 1 1 d . . . H14B H -0.0061 1.8283 -0.2251 0.063 Uiso 1 1 calc R . . C27A C 0.3744(13) 0.9302(6) 0.1106(5) 0.042(2) Uani 1 1 d . . . H27A H 0.4415 0.9563 0.1356 0.051 Uiso 1 1 calc R . . N31A N 0.5178(11) 0.6668(5) 0.2094(4) 0.043(2) Uani 1 1 d . . . H31A H 0.4599 0.6401 0.1867 0.052 Uiso 1 1 calc R . . O21A O 0.2967(10) 0.7829(4) 0.1035(4) 0.064(2) Uani 1 1 d . . . C15A C 0.6562(13) 0.1801(7) 0.3637(6) 0.048(3) Uani 1 1 d . . . H15A H 0.6194 0.1483 0.3326 0.057 Uiso 1 1 calc R . . C22A C 0.1313(13) 1.1510(7) -0.0340(5) 0.047(3) Uani 1 1 d . . . H22A H 0.0759 1.1172 -0.0573 0.056 Uiso 1 1 calc R . . N32A N 0.5001(10) 0.7679(5) 0.1867(4) 0.042(2) Uani 1 1 d . . . H32A H 0.5624 0.7956 0.2067 0.050 Uiso 1 1 calc R . . C13A C 0.6970(13) 0.3323(6) 0.3772(6) 0.040(2) Uani 1 1 d . . . C16B C 0.1886(13) 1.9235(6) -0.1696(6) 0.046(3) Uani 1 1 d . . . H16B H 0.2727 1.9377 -0.1442 0.055 Uiso 1 1 calc R . . C18B C 0.1132(15) 2.1009(7) -0.2360(6) 0.048(3) Uani 1 1 d . . . O202 O 0.8923(13) 1.4767(7) -0.1829(5) 0.102(3) Uani 1 1 d . . . C13B C 0.1734(13) 1.8188(6) -0.1502(6) 0.041(2) Uani 1 1 d . . . C15B C 0.0663(15) 1.6848(7) -0.1644(6) 0.062(3) Uani 1 1 d . . . H15B H -0.0079 1.6632 -0.1896 0.074 Uiso 1 1 calc R . . N32B N -0.0102(11) 2.2666(5) -0.2989(4) 0.047(2) Uani 1 1 d . . . H32B H 0.0603 2.2880 -0.2776 0.056 Uiso 1 1 calc R . . C28B C -0.1276(15) 2.3284(7) -0.3494(6) 0.045(3) Uani 1 1 d . . . N31B N -0.0080(11) 2.1671(5) -0.2828(4) 0.047(2) Uani 1 1 d . . . H31B H -0.0838 2.1474 -0.3026 0.056 Uiso 1 1 calc R . . C21A C 0.1028(15) 1.2516(7) -0.0597(6) 0.054(3) Uani 1 1 d . . . H21A H 0.0251 1.2846 -0.0993 0.065 Uiso 1 1 calc R . . O104 O 0.8361(12) 2.9587(6) -0.3638(5) 0.084(3) Uani 1 1 d . . . C14A C 0.6469(14) 0.2804(7) 0.3355(6) 0.053(3) Uani 1 1 d . . . H14A H 0.6044 0.3140 0.2858 0.063 Uiso 1 1 calc R . . C26B C -0.2133(13) 2.5013(6) -0.4237(6) 0.045(3) Uani 1 1 d . . . H26B H -0.2787 2.4782 -0.4517 0.053 Uiso 1 1 calc R . . C25A C 0.2877(15) 1.2544(7) 0.0282(7) 0.060(3) Uani 1 1 d . . . H25A H 0.3436 1.2898 0.0498 0.072 Uiso 1 1 calc R . . C23B C -0.2239(13) 2.6085(6) -0.4464(6) 0.044(3) Uani 1 1 d . . . C17B C 0.0948(14) 1.9984(6) -0.2193(6) 0.047(3) Uani 1 1 d . . . H17B H 0.0110 1.9853 -0.2456 0.056 Uiso 1 1 calc R . . C22B C -0.2824(15) 2.6700(7) -0.5189(6) 0.057(3) Uani 1 1 d . . . H22B H -0.3143 2.6422 -0.5543 0.068 Uiso 1 1 calc R . . C18A C 0.6250(14) 0.6087(7) 0.2670(6) 0.047(3) Uani 1 1 d . . . O21B O -0.2322(11) 2.2984(5) -0.3772(4) 0.067(2) Uani 1 1 d . . . C25B C -0.1966(14) 2.7547(7) -0.4206(6) 0.055(3) Uani 1 1 d . . . H25B H -0.1682 2.7841 -0.3857 0.066 Uiso 1 1 calc R . . O103 O 0.6826(12) 3.0719(7) -0.3002(6) 0.102(3) Uani 1 1 d . . . C24B C -0.1808(14) 2.6562(7) -0.3971(6) 0.052(3) Uani 1 1 d . . . H24B H -0.1407 2.6195 -0.3475 0.063 Uiso 1 1 calc R . . C11A C 0.7662(15) 0.1757(8) 0.4758(6) 0.060(3) Uani 1 1 d . . . H11A H 0.8087 0.1396 0.5251 0.072 Uiso 1 1 calc R . . O102 O 0.5298(11) 3.0095(5) -0.3703(5) 0.088(3) Uani 1 1 d . . . C21B C -0.2947(15) 2.7700(8) -0.5399(6) 0.059(3) Uani 1 1 d . . . H21B H -0.3344 2.8085 -0.5892 0.071 Uiso 1 1 calc R . . C12A C 0.7594(15) 0.2767(7) 0.4512(6) 0.057(3) Uani 1 1 d . . . H12A H 0.7959 0.3072 0.4834 0.068 Uiso 1 1 calc R . . O11A O 0.7141(9) 0.6446(4) 0.2984(4) 0.056(2) Uani 1 1 d . . . C24A C 0.3185(14) 1.1543(6) 0.0582(6) 0.052(3) Uani 1 1 d . . . H24A H 0.3910 1.1234 0.1000 0.062 Uiso 1 1 calc R . . O201 O 0.6552(12) 1.6081(5) -0.2036(5) 0.094(3) Uani 1 1 d . . . C28A C 0.3850(13) 0.8223(6) 0.1332(5) 0.039(2) Uani 1 1 d . . . C27B C -0.1196(13) 2.4333(6) -0.3670(5) 0.043(2) Uani 1 1 d . . . H27B H -0.0488 2.4524 -0.3385 0.051 Uiso 1 1 calc R . . C16A C 0.6941(12) 0.4382(6) 0.3506(6) 0.042(2) Uani 1 1 d . . . H16A H 0.7480 0.4632 0.3815 0.051 Uiso 1 1 calc R . . C17A C 0.6223(13) 0.5027(6) 0.2866(6) 0.041(2) Uani 1 1 d . . . H17A H 0.5693 0.4805 0.2534 0.049 Uiso 1 1 calc R . . O101 O 0.6371(13) 2.9112(7) -0.2531(5) 0.112(3) Uani 1 1 d . . . C26A C 0.2694(12) 0.9906(6) 0.0548(5) 0.041(2) Uani 1 1 d . . . H26A H 0.2064 0.9607 0.0311 0.049 Uiso 1 1 calc R . . C11B C 0.2687(15) 1.6496(7) -0.0740(7) 0.062(3) Uani 1 1 d . . . H11B H 0.3399 1.6045 -0.0355 0.074 Uiso 1 1 calc R . . C12B C 0.2735(14) 1.7493(7) -0.0926(6) 0.057(3) Uani 1 1 d . . . H12B H 0.3457 1.7697 -0.0655 0.068 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 Ag1 0.0760(7) 0.0189(4) 0.0688(6) -0.0063(4) -0.0138(5) -0.0064(4) Ag2 0.0769(7) 0.0218(4) 0.0785(7) -0.0025(4) -0.0153(5) -0.0055(4) Cl2 0.081(2) 0.0372(14) 0.0561(17) -0.0118(13) -0.0301(16) -0.0066(14) Cl1 0.075(2) 0.0408(14) 0.0562(17) -0.0071(13) -0.0230(16) -0.0137(14) N21B 0.065(6) 0.024(4) 0.063(6) -0.003(4) -0.005(5) 0.005(4) N21A 0.054(6) 0.020(4) 0.057(5) -0.012(4) -0.011(4) 0.000(4) N11B 0.058(6) 0.029(5) 0.065(6) -0.007(4) -0.002(5) -0.008(4) N11A 0.062(6) 0.028(5) 0.059(6) 0.002(4) -0.017(5) -0.002(4) O204 0.106(7) 0.065(5) 0.054(5) -0.021(4) -0.010(4) -0.032(5) O11B 0.078(5) 0.026(4) 0.083(5) -0.011(3) -0.037(5) -0.013(4) C23A 0.046(6) 0.018(4) 0.049(6) -0.014(4) -0.011(5) -0.004(4) O203 0.128(8) 0.059(5) 0.108(7) -0.018(5) -0.039(6) -0.056(5) C14B 0.086(8) 0.027(5) 0.051(7) -0.007(5) -0.026(6) -0.015(5) C27A 0.053(7) 0.025(5) 0.049(6) -0.004(4) -0.016(5) -0.009(4) N31A 0.063(6) 0.014(4) 0.058(5) -0.005(3) -0.026(4) -0.008(4) O21A 0.092(6) 0.022(4) 0.082(5) -0.007(3) -0.049(5) -0.004(4) C15A 0.065(7) 0.038(6) 0.046(6) -0.019(5) -0.004(5) -0.013(5) C22A 0.059(7) 0.042(6) 0.041(6) -0.018(5) -0.012(5) -0.002(5) N32A 0.061(5) 0.018(4) 0.049(5) -0.008(3) -0.023(4) -0.003(4) C13A 0.047(6) 0.025(5) 0.046(6) -0.005(4) -0.002(5) -0.010(4) C16B 0.055(7) 0.032(5) 0.051(6) -0.008(5) -0.014(5) -0.009(5) C18B 0.065(8) 0.025(5) 0.049(6) -0.006(5) -0.011(6) -0.003(5) O202 0.096(7) 0.109(7) 0.103(7) -0.060(6) -0.006(6) 0.017(6) C13B 0.050(6) 0.014(4) 0.056(6) -0.007(4) -0.004(5) -0.003(4) C15B 0.081(9) 0.036(6) 0.070(8) -0.004(6) -0.025(7) -0.017(6) N32B 0.070(6) 0.027(4) 0.050(5) -0.005(4) -0.030(5) -0.012(4) C28B 0.066(8) 0.035(6) 0.035(6) -0.009(5) -0.002(5) -0.012(5) N31B 0.070(6) 0.017(4) 0.059(5) -0.005(4) -0.028(5) -0.012(4) C21A 0.074(8) 0.026(5) 0.063(7) -0.008(5) -0.024(6) -0.004(5) O104 0.095(7) 0.074(6) 0.084(6) -0.032(5) -0.009(5) -0.003(5) C14A 0.072(8) 0.020(5) 0.066(7) -0.003(5) -0.031(6) -0.004(5) C26B 0.055(7) 0.031(5) 0.048(6) -0.011(5) -0.011(5) -0.008(5) C25A 0.069(8) 0.040(6) 0.085(8) -0.032(6) -0.037(7) 0.002(5) C23B 0.050(7) 0.021(5) 0.050(6) -0.002(5) 0.000(5) 0.001(4) C17B 0.066(7) 0.019(5) 0.060(7) -0.004(5) -0.019(6) -0.018(5) C22B 0.084(9) 0.034(6) 0.049(7) -0.005(5) -0.010(6) -0.012(5) C18A 0.058(7) 0.025(5) 0.057(7) -0.011(5) -0.011(6) -0.003(5) O21B 0.086(6) 0.039(4) 0.077(5) 0.001(4) -0.046(5) -0.016(4) C25B 0.075(8) 0.040(6) 0.051(7) -0.020(5) -0.010(6) 0.000(5) O103 0.104(7) 0.095(7) 0.150(8) -0.085(6) -0.020(6) -0.028(6) C24B 0.068(8) 0.024(5) 0.065(7) -0.016(5) -0.021(6) 0.009(5) C11A 0.081(9) 0.046(7) 0.049(7) 0.000(5) -0.020(6) -0.013(6) O102 0.097(7) 0.067(5) 0.107(7) 0.005(5) -0.080(6) -0.018(5) C21B 0.085(9) 0.040(6) 0.046(7) -0.014(5) -0.009(6) 0.005(6) C12A 0.087(9) 0.034(6) 0.058(7) -0.009(5) -0.026(6) -0.020(6) O11A 0.073(5) 0.025(4) 0.075(5) -0.006(3) -0.035(4) -0.015(3) C24A 0.072(8) 0.024(5) 0.062(7) -0.011(5) -0.030(6) 0.001(5) O201 0.116(7) 0.053(5) 0.097(6) 0.018(4) -0.054(6) -0.013(5) C28A 0.051(7) 0.024(5) 0.041(6) -0.003(4) -0.017(5) -0.005(5) C27B 0.053(7) 0.026(5) 0.054(6) -0.017(5) -0.020(5) 0.003(4) C16A 0.039(6) 0.036(5) 0.057(6) -0.014(5) -0.014(5) -0.009(4) C17A 0.056(7) 0.019(5) 0.057(6) -0.020(4) -0.023(5) -0.001(4) O101 0.118(8) 0.103(7) 0.083(6) 0.038(5) -0.027(6) -0.041(6) C26A 0.050(6) 0.018(5) 0.053(6) -0.005(4) -0.012(5) -0.007(4) C11B 0.074(8) 0.025(6) 0.080(8) 0.009(5) -0.030(7) -0.011(5) C12B 0.063(8) 0.031(6) 0.080(8) -0.011(5) -0.033(6) -0.005(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 N11B 2.137(8) . ? Ag1 N21A 2.139(7) . ? Ag2 N21B 2.137(8) 1_626 ? Ag2 N11A 2.138(8) . ? Cl2 O202 1.401(9) . ? Cl2 O201 1.404(7) . ? Cl2 O204 1.417(7) . ? Cl2 O203 1.429(8) . ? Cl1 O101 1.370(8) . ? Cl1 O102 1.406(7) . ? Cl1 O104 1.410(9) . ? Cl1 O103 1.423(8) . ? N21B C21B 1.329(12) . ? N21B C25B 1.352(12) . ? N21B Ag2 2.137(8) 1_484 ? N21A C25A 1.336(11) . ? N21A C21A 1.345(11) . ? N11B C11B 1.331(12) . ? N11B C15B 1.332(12) . ? N11A C15A 1.317(11) . ? N11A C11A 1.330(12) . ? O11B C18B 1.232(11) . ? C23A C24A 1.382(12) . ? C23A C22A 1.392(12) . ? C23A C26A 1.460(11) . ? C14B C13B 1.368(12) . ? C14B C15B 1.376(12) . ? C27A C26A 1.333(11) . ? C27A C28A 1.475(12) . ? N31A C18A 1.354(11) . ? N31A N32A 1.374(9) . ? O21A C28A 1.237(10) . ? C15A C14A 1.370(12) . ? C22A C21A 1.362(12) . ? N32A C28A 1.331(10) . ? C13A C14A 1.353(12) . ? C13A C12A 1.397(12) . ? C13A C16A 1.454(12) . ? C16B C17B 1.309(11) . ? C16B C13B 1.474(12) . ? C18B N31B 1.343(11) . ? C18B C17B 1.455(12) . ? C13B C12B 1.377(12) . ? N32B C28B 1.338(11) . ? N32B N31B 1.378(9) . ? C28B O21B 1.218(11) . ? C28B C27B 1.467(12) . ? C26B C27B 1.333(11) . ? C26B C23B 1.465(12) . ? C25A C24A 1.360(12) . ? C23B C22B 1.387(12) . ? C23B C24B 1.387(13) . ? C22B C21B 1.366(13) . ? C18A O11A 1.226(11) . ? C18A C17A 1.469(12) . ? C25B C24B 1.339(12) . ? C11A C12A 1.381(13) . ? C16A C17A 1.326(11) . ? C11B C12B 1.386(13) . ? 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 N11B Ag1 N21A 171.8(3) . . ? N21B Ag2 N11A 175.0(4) 1_626 . ? O202 Cl2 O201 109.5(6) . . ? O202 Cl2 O204 107.6(5) . . ? O201 Cl2 O204 109.2(5) . . ? O202 Cl2 O203 112.5(6) . . ? O201 Cl2 O203 108.9(5) . . ? O204 Cl2 O203 109.1(5) . . ? O101 Cl1 O102 109.8(6) . . ? O101 Cl1 O104 110.5(6) . . ? O102 Cl1 O104 108.5(6) . . ? O101 Cl1 O103 110.8(6) . . ? O102 Cl1 O103 109.9(5) . . ? O104 Cl1 O103 107.3(5) . . ? C21B N21B C25B 116.5(8) . . ? C21B N21B Ag2 122.1(7) . 1_484 ? C25B N21B Ag2 121.4(7) . 1_484 ? C25A N21A C21A 116.2(8) . . ? C25A N21A Ag1 119.3(7) . . ? C21A N21A Ag1 124.5(6) . . ? C11B N11B C15B 116.4(8) . . ? C11B N11B Ag1 119.4(6) . . ? C15B N11B Ag1 124.1(7) . . ? C15A N11A C11A 116.7(8) . . ? C15A N11A Ag2 121.6(7) . . ? C11A N11A Ag2 121.7(6) . . ? C24A C23A C22A 115.9(8) . . ? C24A C23A C26A 123.8(8) . . ? C22A C23A C26A 120.3(8) . . ? C13B C14B C15B 119.0(9) . . ? C26A C27A C28A 120.5(9) . . ? C18A N31A N32A 121.0(8) . . ? N11A C15A C14A 122.5(9) . . ? C21A C22A C23A 120.7(9) . . ? C28A N32A N31A 118.8(8) . . ? C14A C13A C12A 115.4(8) . . ? C14A C13A C16A 125.6(9) . . ? C12A C13A C16A 118.9(9) . . ? C17B C16B C13B 126.2(9) . . ? O11B C18B N31B 122.0(9) . . ? O11B C18B C17B 123.4(9) . . ? N31B C18B C17B 114.6(10) . . ? C14B C13B C12B 116.6(8) . . ? C14B C13B C16B 124.3(8) . . ? C12B C13B C16B 119.0(9) . . ? N11B C15B C14B 124.8(10) . . ? C28B N32B N31B 116.7(8) . . ? O21B C28B N32B 121.7(9) . . ? O21B C28B C27B 123.8(9) . . ? N32B C28B C27B 114.6(9) . . ? C18B N31B N32B 119.8(8) . . ? N21A C21A C22A 122.9(9) . . ? C13A C14A C15A 122.4(9) . . ? C27B C26B C23B 126.8(9) . . ? N21A C25A C24A 124.1(9) . . ? C22B C23B C24B 115.1(9) . . ? C22B C23B C26B 121.8(10) . . ? C24B C23B C26B 123.1(9) . . ? C16B C17B C18B 124.2(10) . . ? C21B C22B C23B 121.9(10) . . ? O11A C18A N31A 120.8(8) . . ? O11A C18A C17A 125.1(9) . . ? N31A C18A C17A 114.1(9) . . ? C24B C25B N21B 124.2(10) . . ? C25B C24B C23B 120.3(10) . . ? N11A C11A C12A 123.8(9) . . ? N21B C21B C22B 121.9(10) . . ? C11A C12A C13A 119.1(10) . . ? C25A C24A C23A 120.1(9) . . ? O21A C28A N32A 120.9(8) . . ? O21A C28A C27A 123.0(8) . . ? N32A C28A C27A 116.1(9) . . ? C26B C27B C28B 120.3(9) . . ? C17A C16A C13A 126.5(9) . . ? C16A C17A C18A 121.2(9) . . ? C27A C26A C23A 127.2(9) . . ? N11B C11B C12B 121.8(9) . . ? C13B C12B C11B 121.3(10) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.563 _refine_diff_density_min -0.818 _refine_diff_density_rms 0.112 data_2 _database_code_depnum_ccdc_archive 'CCDC 826882' #TrackingRef '- kbrks.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Ag N5 O5' _chemical_formula_weight 464.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.224(3) _cell_length_b 8.903(3) _cell_length_c 12.642(4) _cell_angle_alpha 86.630(11) _cell_angle_beta 80.050(10) _cell_angle_gamma 66.214(9) _cell_volume 834.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2879 _cell_measurement_theta_min 1.64 _cell_measurement_theta_max 25.00 _exptl_crystal_description Plates _exptl_crystal_colour 'Light yellow' _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.848 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 1.250 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.799 _exptl_absorpt_correction_T_max 0.839 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD APEX2' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9742 _diffrn_reflns_av_R_equivalents 0.0864 _diffrn_reflns_av_sigmaI/netI 0.0932 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2879 _reflns_number_gt 1808 _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2879 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1176 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1740 _refine_ls_wR_factor_gt 0.1554 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.002 _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 0.36352(9) 0.53731(8) 0.91271(6) 0.0515(3) Uani 1 1 d . . . N11 N 0.5012(9) 0.3347(8) 0.8021(6) 0.0408(17) Uani 1 1 d . . . C11 C 0.4577(11) 0.2043(11) 0.8126(7) 0.045(2) Uani 1 1 d . . . H11 H 0.3759 0.1995 0.8721 0.054 Uiso 1 1 calc R . . C12 C 0.5289(10) 0.0772(11) 0.7390(7) 0.044(2) Uani 1 1 d . . . H12 H 0.4887 -0.0072 0.7467 0.053 Uiso 1 1 calc R . . C13 C 0.6593(10) 0.0746(10) 0.6542(7) 0.0356(19) Uani 1 1 d . . . C14 C 0.7096(11) 0.2065(10) 0.6457(7) 0.039(2) Uani 1 1 d . . . H14 H 0.7980 0.2091 0.5897 0.047 Uiso 1 1 calc R . . C15 C 0.6296(12) 0.3337(10) 0.7194(7) 0.041(2) Uani 1 1 d . . . H15 H 0.6650 0.4212 0.7120 0.050 Uiso 1 1 calc R . . C16 C 0.7415(11) -0.0564(10) 0.5727(7) 0.040(2) Uani 1 1 d . . . H16 H 0.8413 -0.0555 0.5255 0.048 Uiso 1 1 calc R . . C17 C 0.6909(11) -0.1753(10) 0.5583(7) 0.041(2) Uani 1 1 d . . . H17 H 0.5895 -0.1799 0.6017 0.049 Uiso 1 1 calc R . . N21 N 1.1943(9) -1.2707(8) 0.0250(5) 0.0403(17) Uani 1 1 d . . . C21 C 1.0596(11) -1.2841(10) 0.0935(7) 0.044(2) Uani 1 1 d . . . H21 H 1.0344 -1.3759 0.0876 0.053 Uiso 1 1 calc R . . C22 C 0.9546(11) -1.1700(10) 0.1729(7) 0.041(2) Uani 1 1 d . . . H22 H 0.8660 -1.1883 0.2217 0.049 Uiso 1 1 calc R . . C23 C 0.9831(10) -1.0257(10) 0.1793(7) 0.037(2) Uani 1 1 d . . . C24 C 1.1215(10) -1.0100(10) 0.1069(6) 0.037(2) Uani 1 1 d . . . H24 H 1.1458 -0.9168 0.1079 0.044 Uiso 1 1 calc R . . C25 C 1.2229(11) -1.1340(11) 0.0331(7) 0.043(2) Uani 1 1 d . . . H25 H 1.3171 -1.1223 -0.0141 0.051 Uiso 1 1 calc R . . C26 C 0.8680(10) -0.9018(10) 0.2602(6) 0.037(2) Uani 1 1 d . . . H26 H 0.7754 -0.9219 0.3035 0.045 Uiso 1 1 calc R . . C27 C 0.8827(10) -0.7629(10) 0.2782(7) 0.039(2) Uani 1 1 d . . . H27 H 0.9735 -0.7392 0.2358 0.047 Uiso 1 1 calc R . . O31 O 0.9332(8) -0.3072(8) 0.4170(5) 0.0565(18) Uani 1 1 d . . . O32 O 0.6223(8) -0.6519(7) 0.4143(5) 0.0499(16) Uani 1 1 d . . . N32 N 0.8121(9) -0.5241(8) 0.3787(6) 0.0432(18) Uani 1 1 d . . . H32 H 0.9052 -0.5201 0.3376 0.052 Uiso 1 1 calc R . . N31 N 0.7226(8) -0.4077(8) 0.4574(5) 0.0416(18) Uani 1 1 d . . . H31 H 0.6233 -0.4028 0.4956 0.050 Uiso 1 1 calc R . . C31 C 0.7934(11) -0.3016(10) 0.4737(7) 0.041(2) Uani 1 1 d . . . C32 C 0.7599(11) -0.6447(10) 0.3630(7) 0.040(2) Uani 1 1 d . . . N100 N 0.7116(13) 0.6684(9) 0.8427(8) 0.064(3) Uani 1 1 d . . . O101 O 0.8219(9) 0.6042(10) 0.7632(6) 0.079(2) Uani 1 1 d . . . O102 O 0.7576(18) 0.6860(12) 0.9249(8) 0.128(4) Uani 1 1 d . . . O103 O 0.5529(11) 0.7063(11) 0.8337(8) 0.104(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 0.0480(5) 0.0353(4) 0.0602(5) -0.0248(3) -0.0023(3) -0.0047(3) N11 0.040(4) 0.030(4) 0.050(4) -0.016(3) -0.003(4) -0.011(3) C11 0.035(5) 0.043(5) 0.057(6) -0.019(4) 0.006(4) -0.019(4) C12 0.031(4) 0.039(5) 0.066(6) -0.013(4) -0.003(4) -0.019(4) C13 0.031(4) 0.028(4) 0.045(5) -0.008(4) -0.006(4) -0.008(4) C14 0.033(4) 0.039(5) 0.043(5) -0.006(4) 0.002(4) -0.015(4) C15 0.049(5) 0.023(4) 0.052(6) -0.003(4) -0.013(5) -0.012(4) C16 0.033(4) 0.033(5) 0.045(5) -0.011(4) 0.001(4) -0.005(4) C17 0.034(4) 0.044(5) 0.042(5) -0.017(4) 0.003(4) -0.014(4) N21 0.037(4) 0.039(4) 0.043(4) -0.016(3) -0.002(3) -0.012(3) C21 0.044(5) 0.031(5) 0.059(6) -0.010(4) -0.010(5) -0.015(4) C22 0.037(5) 0.044(5) 0.046(5) -0.008(4) -0.002(4) -0.021(4) C23 0.035(4) 0.030(4) 0.045(5) -0.010(4) -0.003(4) -0.013(4) C24 0.033(4) 0.029(4) 0.047(5) -0.013(4) -0.003(4) -0.012(4) C25 0.037(5) 0.043(5) 0.043(5) -0.013(4) 0.006(4) -0.014(4) C26 0.030(4) 0.034(5) 0.041(5) -0.012(4) 0.006(4) -0.009(4) C27 0.029(4) 0.030(5) 0.048(5) -0.012(4) 0.006(4) -0.002(4) O31 0.054(4) 0.056(4) 0.060(4) -0.027(3) 0.020(3) -0.031(3) O32 0.042(3) 0.050(4) 0.052(4) -0.024(3) 0.017(3) -0.019(3) N32 0.035(4) 0.038(4) 0.048(4) -0.016(3) 0.003(3) -0.007(3) N31 0.029(3) 0.035(4) 0.052(4) -0.024(3) 0.010(3) -0.007(3) C31 0.034(5) 0.034(5) 0.048(5) -0.015(4) 0.000(4) -0.007(4) C32 0.041(5) 0.035(5) 0.039(5) -0.015(4) -0.008(4) -0.006(4) N100 0.063(6) 0.033(5) 0.084(7) -0.014(5) 0.019(5) -0.018(4) O101 0.056(4) 0.075(5) 0.085(6) -0.004(4) 0.025(4) -0.019(4) O102 0.256(15) 0.082(7) 0.077(6) -0.003(5) -0.039(8) -0.095(9) O103 0.058(5) 0.068(6) 0.173(9) -0.012(6) 0.024(6) -0.028(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 N21 2.135(6) 1_476 ? Ag1 N11 2.143(6) . ? Ag1 Ag1 3.2693(17) 2_667 ? N11 C11 1.339(11) . ? N11 C15 1.350(11) . ? C11 C12 1.374(11) . ? C12 C13 1.373(11) . ? C13 C14 1.387(11) . ? C13 C16 1.464(10) . ? C14 C15 1.376(11) . ? C16 C17 1.316(11) . ? C17 C31 1.477(10) . ? N21 C21 1.325(11) . ? N21 C25 1.342(11) . ? N21 Ag1 2.135(6) 1_634 ? C21 C22 1.378(11) . ? C22 C23 1.405(11) . ? C23 C24 1.380(11) . ? C23 C26 1.454(10) . ? C24 C25 1.376(11) . ? C26 C27 1.326(11) . ? C27 C32 1.476(10) . ? O31 C31 1.229(9) . ? O32 C32 1.227(10) . ? N32 C32 1.343(11) . ? N32 N31 1.364(9) . ? N31 C31 1.335(10) . ? N100 O102 1.204(12) . ? N100 O101 1.223(10) . ? N100 O103 1.234(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 N21 Ag1 N11 171.8(3) 1_476 . ? N21 Ag1 Ag1 81.93(18) 1_476 2_667 ? N11 Ag1 Ag1 102.97(19) . 2_667 ? C11 N11 C15 117.7(7) . . ? C11 N11 Ag1 119.8(6) . . ? C15 N11 Ag1 122.5(5) . . ? N11 C11 C12 122.7(8) . . ? C13 C12 C11 120.2(8) . . ? C12 C13 C14 117.0(7) . . ? C12 C13 C16 123.3(8) . . ? C14 C13 C16 119.6(7) . . ? C15 C14 C13 120.6(8) . . ? N11 C15 C14 121.7(8) . . ? C17 C16 C13 127.7(8) . . ? C16 C17 C31 120.6(8) . . ? C21 N21 C25 116.6(7) . . ? C21 N21 Ag1 121.2(5) . 1_634 ? C25 N21 Ag1 122.1(6) . 1_634 ? N21 C21 C22 123.8(8) . . ? C21 C22 C23 119.1(8) . . ? C24 C23 C22 117.2(7) . . ? C24 C23 C26 123.5(7) . . ? C22 C23 C26 119.4(7) . . ? C25 C24 C23 119.2(7) . . ? N21 C25 C24 124.1(8) . . ? C27 C26 C23 126.1(7) . . ? C26 C27 C32 122.3(8) . . ? C32 N32 N31 122.3(7) . . ? C31 N31 N32 118.2(6) . . ? O31 C31 N31 120.3(7) . . ? O31 C31 C17 123.0(8) . . ? N31 C31 C17 116.6(7) . . ? O32 C32 N32 122.2(7) . . ? O32 C32 C27 124.7(7) . . ? N32 C32 C27 113.1(7) . . ? O102 N100 O101 121.4(11) . . ? O102 N100 O103 123.2(11) . . ? O101 N100 O103 115.3(11) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.321 _refine_diff_density_min -1.186 _refine_diff_density_rms 0.158 data_TCHD _database_code_depnum_ccdc_archive 'CCDC 826883' #TrackingRef '- kbrks.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7,8,15,16-tetrakis(4-pyridyl)tricycle[12,2,0,06,9] [3,4,11,12]tetra-aza-cyclohexadecane[2,5,10,13]tetraone, hexa hydrate ; _chemical_name_common ; 7,8,15,16-tetrakis(4-pyridyl)tricycle(12,2,0,06,9) (3,4,11,12)tetra-aza-cyclohexadecane(2,5,10,13)tetraone, hexa hydrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H40 N8 O10' _chemical_formula_weight 696.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.253(6) _cell_length_b 12.694(5) _cell_length_c 17.639(7) _cell_angle_alpha 90.00 _cell_angle_beta 116.174(11) _cell_angle_gamma 90.00 _cell_volume 3467(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3057 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 24.99 _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD APEX2' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20176 _diffrn_reflns_av_R_equivalents 0.0871 _diffrn_reflns_av_sigmaI/netI 0.0526 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3057 _reflns_number_gt 1839 _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3057 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1239 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.2060 _refine_ls_wR_factor_gt 0.1857 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.165 _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 N11 N -0.39774(18) 0.8107(2) -0.0650(2) 0.0560(8) Uani 1 1 d . . . N12 N 0.02808(17) 0.8429(2) -0.01632(17) 0.0454(7) Uani 1 1 d . . . H12 H 0.0697 0.8162 -0.0243 0.055 Uiso 1 1 calc R . . N13 N 0.02843(16) 0.8285(2) 0.06131(17) 0.0471(8) Uani 1 1 d . . . H13 H -0.0083 0.7864 0.0658 0.057 Uiso 1 1 calc R . . O17 O -0.02956(15) 0.9049(2) -0.14785(16) 0.0607(8) Uani 1 1 d . . . O18 O 0.08839(15) 0.8627(2) 0.19988(15) 0.0602(8) Uani 1 1 d . . . C10 C -0.3343(2) 0.8748(3) -0.0184(3) 0.0615(11) Uani 1 1 d . . . H10 H -0.3344 0.9020 0.0305 0.074 Uiso 1 1 calc R . . C11 C -0.2676(2) 0.9043(3) -0.0374(2) 0.0544(10) Uani 1 1 d . . . H11 H -0.2259 0.9518 -0.0030 0.065 Uiso 1 1 calc R . . C12 C -0.26349(19) 0.8625(2) -0.1076(2) 0.0401(8) Uani 1 1 d . . . C13 C -0.3297(2) 0.7967(3) -0.1562(2) 0.0641(12) Uani 1 1 d . . . H13A H -0.3309 0.7675 -0.2051 0.077 Uiso 1 1 calc R . . C14 C -0.3943(2) 0.7734(3) -0.1336(3) 0.0652(12) Uani 1 1 d . . . H14 H -0.4383 0.7287 -0.1685 0.078 Uiso 1 1 calc R . . C15 C -0.19490(19) 0.8835(3) -0.1355(2) 0.0420(8) Uani 1 1 d . . . H15 H -0.1815 0.8202 -0.1593 0.050 Uiso 1 1 calc R . . C16 C -0.11035(19) 0.9390(3) -0.0695(2) 0.0414(8) Uani 1 1 d . . . H16 H -0.1032 0.9383 -0.0112 0.050 Uiso 1 1 calc R . . C17 C -0.0341(2) 0.8967(3) -0.0806(2) 0.0428(9) Uani 1 1 d . . . C18 C 0.0859(2) 0.8799(3) 0.1303(2) 0.0415(8) Uani 1 1 d . . . N21 N -0.4682(2) 1.0906(4) -0.3536(3) 0.0905(14) Uani 1 1 d . . . C21 C -0.4374(3) 1.0008(5) -0.3672(3) 0.0908(17) Uani 1 1 d . . . H21 H -0.4736 0.9599 -0.4129 0.109 Uiso 1 1 calc R . . C22 C -0.3546(2) 0.9639(3) -0.3177(2) 0.0723(13) Uani 1 1 d . . . H22 H -0.3364 0.9005 -0.3309 0.087 Uiso 1 1 calc R . . C23 C -0.2992(2) 1.0219(3) -0.2488(2) 0.0493(9) Uani 1 1 d . . . C24 C -0.3299(2) 1.1158(3) -0.2348(3) 0.0706(12) Uani 1 1 d . . . H24 H -0.2951 1.1587 -0.1899 0.085 Uiso 1 1 calc R . . C25 C -0.4135(3) 1.1462(4) -0.2885(3) 0.0892(15) Uani 1 1 d . . . H25 H -0.4327 1.2106 -0.2779 0.107 Uiso 1 1 calc R . . C26 C -0.20966(18) 0.9825(3) -0.19484(19) 0.0430(9) Uani 1 1 d . . . H26 H -0.1817 0.9686 -0.2316 0.052 Uiso 1 1 calc R . . C27 C -0.14621(18) 1.0443(2) -0.11787(19) 0.0391(8) Uani 1 1 d . . . H27 H -0.1783 1.0816 -0.0921 0.047 Uiso 1 1 calc R . . O1W O -0.62778(17) 1.1892(2) -0.45055(19) 0.0844(10) Uani 1 1 d . . . O2W O -0.7234(2) 1.3299(3) -0.3979(2) 0.1155(13) Uani 1 1 d . . . O3W O 0.11367(17) 1.0012(2) -0.15601(18) 0.0840(10) 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 N11 0.0406(16) 0.059(2) 0.070(2) 0.0047(17) 0.0254(15) -0.0113(15) N12 0.0347(15) 0.0528(18) 0.0489(17) 0.0018(14) 0.0185(13) -0.0018(13) N13 0.0375(15) 0.0510(18) 0.0501(17) 0.0080(14) 0.0167(13) -0.0110(13) O17 0.0468(15) 0.087(2) 0.0541(16) 0.0110(14) 0.0275(13) 0.0072(13) O18 0.0524(15) 0.0739(19) 0.0498(15) 0.0126(13) 0.0184(12) -0.0160(13) C10 0.057(2) 0.068(3) 0.072(3) -0.015(2) 0.040(2) -0.017(2) C11 0.046(2) 0.054(2) 0.065(2) -0.0154(19) 0.0271(19) -0.0207(17) C12 0.0332(17) 0.0384(19) 0.0475(19) 0.0004(16) 0.0169(15) -0.0050(14) C13 0.058(2) 0.079(3) 0.057(2) -0.021(2) 0.027(2) -0.035(2) C14 0.054(2) 0.075(3) 0.065(3) -0.013(2) 0.025(2) -0.034(2) C15 0.0338(17) 0.041(2) 0.0474(19) 0.0000(15) 0.0146(15) -0.0068(14) C16 0.0322(16) 0.049(2) 0.0432(18) 0.0021(16) 0.0165(14) -0.0059(14) C17 0.0327(18) 0.046(2) 0.048(2) 0.0020(16) 0.0167(16) -0.0077(15) C18 0.0330(18) 0.042(2) 0.045(2) 0.0071(16) 0.0139(16) -0.0021(14) N21 0.045(2) 0.097(3) 0.104(3) 0.033(3) 0.009(2) -0.005(2) C21 0.055(3) 0.104(4) 0.074(3) 0.014(3) -0.008(2) -0.022(3) C22 0.048(2) 0.082(3) 0.064(3) -0.004(2) 0.004(2) -0.007(2) C23 0.0331(17) 0.060(3) 0.052(2) 0.0104(18) 0.0156(16) -0.0094(17) C24 0.044(2) 0.072(3) 0.078(3) 0.003(2) 0.010(2) 0.002(2) C25 0.061(3) 0.083(3) 0.114(4) 0.019(3) 0.030(3) 0.012(3) C26 0.0302(16) 0.056(2) 0.0406(19) 0.0016(16) 0.0134(14) -0.0062(15) C27 0.0308(16) 0.0392(19) 0.0442(19) 0.0043(15) 0.0139(15) -0.0038(14) O1W 0.0560(17) 0.079(2) 0.100(2) 0.0083(17) 0.0184(16) -0.0062(15) O2W 0.087(2) 0.114(3) 0.122(3) -0.013(2) 0.024(2) 0.014(2) O3W 0.0681(18) 0.108(2) 0.0721(19) 0.0005(17) 0.0271(16) -0.0043(18) _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 N11 C14 1.324(5) . ? N11 C10 1.320(4) . ? N12 C17 1.353(4) . ? N12 N13 1.379(4) . ? N13 C18 1.351(4) . ? O17 C17 1.228(4) . ? O18 C18 1.228(4) . ? C10 C11 1.385(5) . ? C11 C12 1.378(5) . ? C12 C13 1.369(4) . ? C12 C15 1.492(4) . ? C13 C14 1.371(5) . ? C15 C16 1.576(4) . ? C15 C26 1.583(4) . ? C16 C17 1.511(4) . ? C16 C27 1.559(4) . ? C18 C27 1.503(4) 5_575 ? N21 C21 1.323(6) . ? N21 C25 1.324(6) . ? C21 C22 1.387(6) . ? C22 C23 1.381(5) . ? C23 C24 1.371(5) . ? C23 C26 1.498(4) . ? C24 C25 1.386(6) . ? C26 C27 1.531(4) . ? C27 C18 1.503(4) 5_575 ? 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 C14 N11 C10 115.5(3) . . ? C17 N12 N13 123.6(3) . . ? C18 N13 N12 120.8(3) . . ? N11 C10 C11 124.4(4) . . ? C12 C11 C10 119.4(3) . . ? C11 C12 C13 116.0(3) . . ? C11 C12 C15 126.2(3) . . ? C13 C12 C15 117.8(3) . . ? C14 C13 C12 120.7(4) . . ? N11 C14 C13 123.9(3) . . ? C12 C15 C16 116.5(3) . . ? C12 C15 C26 116.1(3) . . ? C16 C15 C26 87.7(2) . . ? C17 C16 C27 113.1(3) . . ? C17 C16 C15 108.7(3) . . ? C27 C16 C15 88.0(2) . . ? O17 C17 N12 119.2(3) . . ? O17 C17 C16 121.7(3) . . ? N12 C17 C16 119.0(3) . . ? O18 C18 N13 120.2(3) . . ? O18 C18 C27 122.6(3) . 5_575 ? N13 C18 C27 117.2(3) . 5_575 ? C21 N21 C25 115.3(4) . . ? N21 C21 C22 124.2(4) . . ? C23 C22 C21 119.7(5) . . ? C24 C23 C22 116.7(3) . . ? C24 C23 C26 123.2(3) . . ? C22 C23 C26 120.0(4) . . ? C23 C24 C25 119.2(4) . . ? N21 C25 C24 124.9(5) . . ? C23 C26 C27 121.7(3) . . ? C23 C26 C15 120.3(3) . . ? C27 C26 C15 88.7(2) . . ? C18 C27 C26 117.9(3) 5_575 . ? C18 C27 C16 119.7(2) 5_575 . ? C26 C27 C16 90.1(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.330 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.055 data_MCB _database_code_depnum_ccdc_archive 'CCDC 826884' #TrackingRef '- kbrks.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; r-1,t-3-bis(4-pyridyl)-c-2,t-4-bis(N-(3(4-pyridyl)acryloyl) -hydrazinocarbonyl)cyclobutane,tetra hydrate ; _chemical_name_common ; r-1,t-3-bis(4-pyridyl)-c-2,t-4-bis(N-(3(4-pyridyl)acryloyl) - hydrazinocarbonyl)cyclobutane,tetra hydrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H36 N8 O8' _chemical_formula_weight 660.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.7469(9) _cell_length_b 9.6101(18) _cell_length_c 17.895(3) _cell_angle_alpha 84.941(6) _cell_angle_beta 84.373(8) _cell_angle_gamma 80.613(6) _cell_volume 799.4(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2625 _cell_measurement_theta_min 1.15 _cell_measurement_theta_max 25 _exptl_crystal_description Plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.983 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD APEX2' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7661 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2625 _reflns_number_gt 1834 _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2625 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0973 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_ref 0.2007 _refine_ls_wR_factor_gt 0.1796 _refine_ls_goodness_of_fit_ref 1.242 _refine_ls_restrained_S_all 1.242 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.001 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 N1 N 1.3753(5) 1.2442(2) -0.35826(13) 0.0291(6) Uani 1 1 d . . . H1 H 1.1933 1.2633 -0.3615 0.035 Uiso 1 1 calc R . . N2 N 1.4845(5) 1.1400(3) -0.30559(14) 0.0334(7) Uani 1 1 d . . . H2 H 1.6554 1.0945 -0.3128 0.040 Uiso 1 1 calc R . . O11 O 1.0759(5) 1.1756(3) -0.22957(14) 0.0611(8) Uani 1 1 d . . . N11 N 1.6395(8) 0.6474(4) 0.04106(19) 0.0657(10) Uani 1 1 d . . . C11 C 1.4240(13) 0.7419(5) 0.0543(2) 0.0850(16) Uani 1 1 d . . . H11 H 1.3344 0.7432 0.1029 0.102 Uiso 1 1 calc R . . C12 C 1.3169(14) 0.8418(7) 0.0008(3) 0.130(3) Uani 1 1 d . . . H12 H 1.1574 0.9077 0.0141 0.156 Uiso 1 1 calc R . . C13 C 1.4381(8) 0.8474(4) -0.07154(19) 0.0500(10) Uani 1 1 d . . . C14 C 1.6615(11) 0.7471(5) -0.0858(2) 0.0747(15) Uani 1 1 d . . . H14 H 1.7517 0.7417 -0.1343 0.090 Uiso 1 1 calc R . . C15 C 1.7575(14) 0.6517(6) -0.0285(3) 0.116(2) Uani 1 1 d . . . H15 H 1.9182 0.5851 -0.0398 0.139 Uiso 1 1 calc R . . C16 C 1.3260(9) 0.9555(5) -0.1286(2) 0.0645(12) Uani 1 1 d . . . H16 H 1.1402 1.0014 -0.1177 0.077 Uiso 1 1 calc R . . C17 C 1.4538(8) 0.9950(3) -0.19238(18) 0.0385(8) Uani 1 1 d . . . H17 H 1.6363 0.9488 -0.2068 0.046 Uiso 1 1 calc R . . C18 C 1.3169(7) 1.1119(3) -0.24311(17) 0.0351(8) Uani 1 1 d . . . O21 O 1.8098(4) 1.2919(2) -0.40376(12) 0.0374(6) Uani 1 1 d . . . N21 N 0.9429(6) 1.9189(3) -0.35723(16) 0.0439(8) Uani 1 1 d . . . C21 C 0.9302(8) 1.7842(4) -0.3351(2) 0.0492(9) Uani 1 1 d . . . H21 H 0.7935 1.7651 -0.2963 0.059 Uiso 1 1 calc R . . C22 C 1.1053(7) 1.6709(3) -0.36575(18) 0.0392(8) Uani 1 1 d . . . H22 H 1.0875 1.5790 -0.3472 0.047 Uiso 1 1 calc R . . C23 C 1.3084(6) 1.6952(3) -0.42454(16) 0.0279(7) Uani 1 1 d . . . C24 C 1.3258(7) 1.8345(3) -0.44706(18) 0.0382(8) Uani 1 1 d . . . H24 H 1.4618 1.8567 -0.4854 0.046 Uiso 1 1 calc R . . C25 C 1.1412(8) 1.9413(3) -0.41278(19) 0.0401(8) Uani 1 1 d . . . H25 H 1.1567 2.0344 -0.4296 0.048 Uiso 1 1 calc R . . C26 C 1.5070(6) 1.5728(3) -0.45719(15) 0.0247(7) Uani 1 1 d . . . H26 H 1.6813 1.5570 -0.4304 0.030 Uiso 1 1 calc R . . C27 C 1.3999(6) 1.4291(3) -0.45671(15) 0.0241(7) Uani 1 1 d . . . H27 H 1.1912 1.4391 -0.4467 0.029 Uiso 1 1 calc R . . C28 C 1.5504(6) 1.3152(3) -0.40401(15) 0.0240(7) Uani 1 1 d . . . O1W O 0.2476(8) 1.5329(4) -0.1773(2) 0.0833(12) Uani 1 1 d . . . H1W2 H 0.579(9) 1.479(4) -0.223(2) 0.050 Uiso 1 1 d . . . H2W2 H 0.828(9) 1.386(5) -0.248(2) 0.050 Uiso 1 1 d . . . O2W O 0.7797(9) 1.4641(4) -0.2495(2) 0.0840(11) Uani 1 1 d . . . H1W1 H 0.250(8) 1.486(4) -0.135(2) 0.050 Uiso 1 1 d . . . H2W1 H 0.150(9) 1.514(5) -0.197(3) 0.050 Uiso 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 N1 0.0248(14) 0.0277(14) 0.0316(14) 0.0096(11) -0.0012(11) -0.0020(11) N2 0.0302(15) 0.0306(15) 0.0336(15) 0.0104(11) 0.0011(12) 0.0033(11) O11 0.0476(17) 0.0677(19) 0.0501(16) 0.0219(13) 0.0150(13) 0.0189(14) N11 0.083(3) 0.060(2) 0.047(2) 0.0221(16) -0.0099(19) 0.000(2) C11 0.118(4) 0.080(3) 0.038(2) 0.023(2) 0.015(3) 0.015(3) C12 0.146(5) 0.130(5) 0.058(3) 0.050(3) 0.051(3) 0.082(4) C13 0.056(2) 0.050(2) 0.036(2) 0.0159(16) 0.0057(18) -0.0007(19) C14 0.103(4) 0.062(3) 0.038(2) 0.0189(19) 0.016(2) 0.025(3) C15 0.141(5) 0.097(4) 0.065(3) 0.039(3) 0.029(3) 0.062(4) C16 0.058(3) 0.071(3) 0.046(2) 0.024(2) 0.012(2) 0.019(2) C17 0.045(2) 0.0348(19) 0.0303(17) 0.0060(13) 0.0020(15) 0.0022(15) C18 0.038(2) 0.0334(18) 0.0298(17) 0.0051(13) 0.0046(15) -0.0017(15) O21 0.0227(12) 0.0390(13) 0.0486(14) 0.0124(10) -0.0053(10) -0.0065(10) N21 0.0503(19) 0.0323(16) 0.0458(17) -0.0089(13) 0.0044(15) 0.0012(14) C21 0.056(2) 0.040(2) 0.047(2) -0.0040(16) 0.0146(18) -0.0049(18) C22 0.049(2) 0.0277(18) 0.0366(18) 0.0008(14) 0.0079(16) -0.0027(15) C23 0.0309(17) 0.0238(16) 0.0283(16) -0.0007(12) -0.0034(14) -0.0023(13) C24 0.045(2) 0.0284(18) 0.0399(19) -0.0027(14) 0.0103(16) -0.0093(15) C25 0.050(2) 0.0230(17) 0.045(2) -0.0029(14) 0.0014(17) -0.0048(15) C26 0.0235(16) 0.0224(15) 0.0279(15) 0.0022(11) -0.0034(12) -0.0041(12) C27 0.0200(15) 0.0211(15) 0.0289(15) 0.0036(11) 0.0019(12) -0.0015(12) C28 0.0197(16) 0.0242(15) 0.0291(15) -0.0017(12) -0.0006(12) -0.0077(12) O1W 0.089(3) 0.100(3) 0.053(2) 0.0199(19) -0.0094(18) -0.003(2) O2W 0.079(2) 0.061(2) 0.103(3) 0.003(2) 0.028(2) -0.010(2) _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 N1 C28 1.334(3) . ? N1 N2 1.386(3) . ? N2 C18 1.341(4) . ? O11 C18 1.219(4) . ? N11 C11 1.271(5) . ? N11 C15 1.314(6) . ? C11 C12 1.368(6) . ? C12 C13 1.364(6) . ? C13 C14 1.332(5) . ? C13 C16 1.464(5) . ? C14 C15 1.375(6) . ? C16 C17 1.296(5) . ? C17 C18 1.486(4) . ? O21 C28 1.215(3) . ? N21 C25 1.329(4) . ? N21 C21 1.329(4) . ? C21 C22 1.377(5) . ? C22 C23 1.386(4) . ? C23 C24 1.377(4) . ? C23 C26 1.505(4) . ? C24 C25 1.382(4) . ? C26 C27 1.546(4) . ? C26 C27 1.561(4) 2_884 ? C27 C28 1.514(4) . ? C27 C26 1.561(4) 2_884 ? 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 C28 N1 N2 120.5(2) . . ? C18 N2 N1 118.3(2) . . ? C11 N11 C15 115.4(4) . . ? N11 C11 C12 123.4(4) . . ? C13 C12 C11 121.7(5) . . ? C14 C13 C12 115.0(3) . . ? C14 C13 C16 123.3(3) . . ? C12 C13 C16 121.7(4) . . ? C13 C14 C15 119.5(4) . . ? N11 C15 C14 124.9(5) . . ? C17 C16 C13 128.0(4) . . ? C16 C17 C18 121.8(3) . . ? O11 C18 N2 123.3(3) . . ? O11 C18 C17 123.4(3) . . ? N2 C18 C17 113.3(3) . . ? C25 N21 C21 115.7(3) . . ? N21 C21 C22 124.5(3) . . ? C21 C22 C23 119.4(3) . . ? C24 C23 C22 116.4(3) . . ? C24 C23 C26 123.4(3) . . ? C22 C23 C26 120.1(3) . . ? C23 C24 C25 120.1(3) . . ? N21 C25 C24 123.8(3) . . ? C23 C26 C27 118.9(2) . . ? C23 C26 C27 121.9(2) . 2_884 ? C27 C26 C27 91.1(2) . 2_884 ? C28 C27 C26 113.3(2) . . ? C28 C27 C26 118.2(2) . 2_884 ? C26 C27 C26 88.9(2) . 2_884 ? O21 C28 N1 123.4(3) . . ? O21 C28 C27 122.1(3) . . ? N1 C28 C27 114.5(2) . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.328 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.070