# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Jochen Mattay' _publ_contact_author_email OC1JM@UNI-BIELEFELD.DE _publ_section_title ; Controlling the self assembly of arene functionalised 2-aminopyrimidines by arene-perfluoroarene interaction and by silver(I) complex formation ; loop_ _publ_author_name 'Jochen Mattay' 'Ralf Brodbeck' 'Beate Neumann' 'Hans-Georg Stammler' 'Ion Stoll' # Attachment 'ION06_18_09_12_16_13_15_19_20_21.CIF' data_compound4 _database_code_depnum_ccdc_archive 'CCDC 693050' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H9 N3' _chemical_formula_sum 'C10 H9 N3' _chemical_formula_weight 171.20 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 17.8896(8) _cell_length_b 7.3769(4) _cell_length_c 6.7820(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.310(3) _cell_angle_gamma 90.00 _cell_volume 887.74(8) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 14218 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description 'fragment, plate' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9777 _exptl_absorpt_correction_T_max 0.9936 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14062 _diffrn_reflns_av_R_equivalents 0.063 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2024 _reflns_number_gt 1452 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0733P)^2^+0.0737P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.021(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2024 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1361 _refine_ls_wR_factor_gt 0.1246 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 N1 N 0.40062(6) 0.12929(16) 0.69114(19) 0.0391(3) Uani 1 1 d . . . N2 N 0.51020(6) -0.03336(17) 0.76117(18) 0.0374(3) Uani 1 1 d . . . H2A H 0.5315 0.0644 0.8176 0.045 Uiso 1 1 calc R . . H2B H 0.5364 -0.1340 0.7575 0.045 Uiso 1 1 calc R . . N3 N 0.40764(6) -0.18205(15) 0.59440(17) 0.0334(3) Uani 1 1 d . . . C1 C 0.43822(7) -0.02900(18) 0.6813(2) 0.0319(3) Uani 1 1 d . . . C2 C 0.33649(7) -0.17075(19) 0.5123(2) 0.0324(3) Uani 1 1 d . . . H2 H 0.3141 -0.2761 0.4495 0.039 Uiso 1 1 calc R . . C3 C 0.29203(7) -0.01455(18) 0.5114(2) 0.0326(3) Uani 1 1 d . . . C4 C 0.32956(7) 0.1326(2) 0.6071(2) 0.0384(4) Uani 1 1 d . . . H4 H 0.3024 0.2427 0.6126 0.046 Uiso 1 1 calc R . . C5 C 0.21224(7) -0.00776(18) 0.4232(2) 0.0342(3) Uani 1 1 d . . . C6 C 0.18527(8) -0.1132(2) 0.2594(2) 0.0405(4) Uani 1 1 d . . . H6 H 0.2192 -0.1895 0.2012 0.049 Uiso 1 1 calc R . . C7 C 0.11021(8) -0.1098(2) 0.1793(2) 0.0450(4) Uani 1 1 d . . . H7 H 0.0932 -0.1844 0.0685 0.054 Uiso 1 1 calc R . . C8 C 0.05999(8) 0.0014(2) 0.2594(2) 0.0437(4) Uani 1 1 d . . . H8 H 0.0085 0.0049 0.2038 0.052 Uiso 1 1 calc R . . C9 C 0.08551(8) 0.1076(2) 0.4214(2) 0.0430(4) Uani 1 1 d . . . H9 H 0.0512 0.1843 0.4778 0.052 Uiso 1 1 calc R . . C10 C 0.16022(8) 0.1037(2) 0.5025(2) 0.0390(4) Uani 1 1 d . . . H10 H 0.1767 0.1779 0.6141 0.047 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 N1 0.0351(6) 0.0345(7) 0.0460(8) -0.0036(6) -0.0017(5) 0.0000(5) N2 0.0352(6) 0.0317(7) 0.0437(7) -0.0017(5) -0.0018(5) 0.0003(5) N3 0.0340(6) 0.0325(7) 0.0336(6) 0.0002(5) 0.0038(5) -0.0002(5) C1 0.0341(7) 0.0323(8) 0.0292(7) 0.0028(6) 0.0032(5) -0.0009(5) C2 0.0342(7) 0.0324(8) 0.0309(7) -0.0017(6) 0.0050(5) -0.0036(5) C3 0.0331(7) 0.0346(8) 0.0299(7) 0.0004(6) 0.0029(5) -0.0008(5) C4 0.0374(8) 0.0322(8) 0.0445(9) -0.0020(6) 0.0013(6) 0.0024(6) C5 0.0341(7) 0.0343(8) 0.0338(8) 0.0016(6) 0.0032(6) -0.0009(5) C6 0.0378(8) 0.0444(9) 0.0386(8) -0.0074(7) 0.0023(6) 0.0027(6) C7 0.0426(8) 0.0507(10) 0.0396(9) -0.0070(7) -0.0026(6) -0.0018(7) C8 0.0321(7) 0.0515(9) 0.0454(9) 0.0058(7) -0.0027(6) 0.0009(6) C9 0.0375(8) 0.0448(9) 0.0469(9) -0.0014(7) 0.0054(6) 0.0066(6) C10 0.0392(8) 0.0388(8) 0.0382(8) -0.0044(6) 0.0014(6) 0.0012(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 N1 C4 1.3254(16) . ? N1 C1 1.3535(18) . ? N2 C1 1.3324(16) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 C2 1.3254(16) . ? N3 C1 1.3562(17) . ? C2 C3 1.3997(19) . ? C2 H2 0.9500 . ? C3 C4 1.3924(19) . ? C3 C5 1.4769(18) . ? C4 H4 0.9500 . ? C5 C6 1.391(2) . ? C5 C10 1.399(2) . ? C6 C7 1.3832(19) . ? C6 H6 0.9500 . ? C7 C8 1.378(2) . ? C7 H7 0.9500 . ? C8 C9 1.379(2) . ? C8 H8 0.9500 . ? C9 C10 1.3794(18) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? 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 C4 N1 C1 116.74(11) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C2 N3 C1 116.29(11) . . ? N2 C1 N1 117.48(11) . . ? N2 C1 N3 118.18(11) . . ? N1 C1 N3 124.35(12) . . ? N3 C2 C3 124.63(12) . . ? N3 C2 H2 117.7 . . ? C3 C2 H2 117.7 . . ? C4 C3 C2 113.56(12) . . ? C4 C3 C5 123.12(12) . . ? C2 C3 C5 123.30(12) . . ? N1 C4 C3 124.43(13) . . ? N1 C4 H4 117.8 . . ? C3 C4 H4 117.8 . . ? C6 C5 C10 117.09(13) . . ? C6 C5 C3 121.58(12) . . ? C10 C5 C3 121.33(12) . . ? C7 C6 C5 121.61(13) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 C7 C6 120.33(14) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 119.07(13) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C8 C9 C10 120.75(13) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C5 121.15(13) . . ? C9 C10 H10 119.4 . . ? C5 C10 H10 119.4 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.171 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.038 #============================================================================== data_compound4b _database_code_depnum_ccdc_archive 'CCDC 693051' _audit_creation_method ion18 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H9 N3' _chemical_formula_sum 'C10 H9 N3' _chemical_formula_weight 171.20 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/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 36.2306(16) _cell_length_b 5.48990(10) _cell_length_c 26.4460(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.6441(12) _cell_angle_gamma 90.00 _cell_volume 5234.7(3) _cell_formula_units_Z 24 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 25670 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 25.028 _exptl_crystal_description needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2160 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9757 _exptl_absorpt_correction_T_max 0.9975 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17873 _diffrn_reflns_av_R_equivalents 0.053 _diffrn_reflns_av_sigmaI/netI 0.0665 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4602 _reflns_number_gt 2808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0576P)^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 4602 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 N1 N 0.25430(5) 1.0328(3) 0.44756(7) 0.0354(5) Uani 1 1 d . . . N2 N 0.20615(5) 1.0449(3) 0.49750(7) 0.0428(5) Uani 1 1 d . . . H2A H 0.1855 0.9858 0.5075 0.051 Uiso 1 1 calc R . . H2B H 0.2159 1.1786 0.5114 0.051 Uiso 1 1 calc R . . N3 N 0.20692(5) 0.7280(3) 0.44067(7) 0.0407(5) Uani 1 1 d . . . N4 N 0.14633(5) 0.8244(3) 0.55399(6) 0.0335(4) Uani 1 1 d . . . N5 N 0.14414(5) 0.4691(3) 0.50709(7) 0.0397(5) Uani 1 1 d . . . H5A H 0.1334 0.3306 0.4976 0.048 Uiso 1 1 calc R . . H5B H 0.1651 0.5115 0.4953 0.048 Uiso 1 1 calc R . . N6 N 0.09659(5) 0.5413(3) 0.55639(7) 0.0363(5) Uani 1 1 d . . . N7 N 0.09054(5) 0.0331(3) 0.45977(7) 0.0348(5) Uani 1 1 d . . . N8 N 0.04408(5) 0.1892(3) 0.50382(7) 0.0447(5) Uani 1 1 d . . . H8A H 0.0214 0.1845 0.5131 0.054 Uiso 1 1 calc R . . H8B H 0.0593 0.3068 0.5149 0.054 Uiso 1 1 calc R . . N9 N 0.03071(5) -0.1572(3) 0.45739(7) 0.0393(5) Uani 1 1 d . . . C1 C 0.22260(6) 0.9320(4) 0.46121(8) 0.0333(5) Uani 1 1 d . . . C2 C 0.22401(6) 0.6270(4) 0.40377(9) 0.0416(6) Uani 1 1 d . . . H2 H 0.2135 0.4824 0.3888 0.050 Uiso 1 1 calc R . . C3 C 0.25614(6) 0.7156(4) 0.38519(8) 0.0316(5) Uani 1 1 d . . . C4 C 0.26986(6) 0.9224(4) 0.41053(8) 0.0340(5) Uani 1 1 d . . . H4 H 0.2922 0.9902 0.4006 0.041 Uiso 1 1 calc R . . C5 C 0.27373(6) 0.6024(4) 0.34295(8) 0.0320(5) Uani 1 1 d . . . C6 C 0.26152(6) 0.3814(4) 0.32121(8) 0.0384(6) Uani 1 1 d . . . H6 H 0.2419 0.2966 0.3349 0.046 Uiso 1 1 calc R . . C7 C 0.27726(7) 0.2830(4) 0.28027(9) 0.0451(6) Uani 1 1 d . . . H7 H 0.2685 0.1318 0.2664 0.054 Uiso 1 1 calc R . . C8 C 0.30566(7) 0.4024(4) 0.25947(9) 0.0487(7) Uani 1 1 d . . . H8 H 0.3162 0.3362 0.2310 0.058 Uiso 1 1 calc R . . C9 C 0.31848(7) 0.6184(4) 0.28061(9) 0.0491(7) Uani 1 1 d . . . H9 H 0.3383 0.7009 0.2669 0.059 Uiso 1 1 calc R . . C10 C 0.30296(6) 0.7172(4) 0.32163(8) 0.0404(6) Uani 1 1 d . . . H10 H 0.3124 0.8667 0.3357 0.048 Uiso 1 1 calc R . . C11 C 0.12851(6) 0.6165(4) 0.53980(8) 0.0314(5) Uani 1 1 d . . . C12 C 0.08198(6) 0.6870(4) 0.58943(8) 0.0361(6) Uani 1 1 d . . . H12 H 0.0595 0.6369 0.6020 0.043 Uiso 1 1 calc R . . C13 C 0.09727(6) 0.9062(3) 0.60670(8) 0.0308(5) Uani 1 1 d . . . C14 C 0.12999(6) 0.9634(4) 0.58682(8) 0.0339(5) Uani 1 1 d . . . H14 H 0.1418 1.1123 0.5972 0.041 Uiso 1 1 calc R . . C15 C 0.07962(6) 1.0653(3) 0.64279(8) 0.0334(5) Uani 1 1 d . . . C16 C 0.04131(7) 1.0636(4) 0.64441(9) 0.0423(6) Uani 1 1 d . . . H16 H 0.0264 0.9602 0.6220 0.051 Uiso 1 1 calc R . . C17 C 0.02468(7) 1.2112(4) 0.67830(9) 0.0491(7) Uani 1 1 d . . . H17 H -0.0015 1.2070 0.6792 0.059 Uiso 1 1 calc R . . C18 C 0.04592(8) 1.3630(4) 0.71045(9) 0.0519(7) Uani 1 1 d . . . H18 H 0.0345 1.4638 0.7336 0.062 Uiso 1 1 calc R . . C19 C 0.08379(7) 1.3697(4) 0.70927(9) 0.0493(7) Uani 1 1 d . . . H19 H 0.0985 1.4756 0.7314 0.059 Uiso 1 1 calc R . . C20 C 0.10041(7) 1.2208(4) 0.67564(8) 0.0417(6) Uani 1 1 d . . . H20 H 0.1266 1.2257 0.6751 0.050 Uiso 1 1 calc R . . C21 C 0.05542(6) 0.0175(4) 0.47291(8) 0.0329(5) Uani 1 1 d . . . C22 C 0.04255(6) -0.3238(4) 0.42618(8) 0.0403(6) Uani 1 1 d . . . H22 H 0.0259 -0.4511 0.4152 0.048 Uiso 1 1 calc R . . C23 C 0.07718(6) -0.3257(3) 0.40858(8) 0.0326(5) Uani 1 1 d . . . C24 C 0.10012(6) -0.1376(4) 0.42796(8) 0.0358(5) Uani 1 1 d . . . H24 H 0.1245 -0.1307 0.4176 0.043 Uiso 1 1 calc R . . C25 C 0.08874(6) -0.5149(4) 0.37350(8) 0.0349(6) Uani 1 1 d . . . C26 C 0.06268(7) -0.6511(4) 0.34292(8) 0.0410(6) Uani 1 1 d . . . H26 H 0.0370 -0.6168 0.3436 0.049 Uiso 1 1 calc R . . C27 C 0.07346(7) -0.8347(4) 0.31163(9) 0.0462(6) Uani 1 1 d . . . H27 H 0.0552 -0.9259 0.2915 0.055 Uiso 1 1 calc R . . C28 C 0.11055(8) -0.8859(4) 0.30958(9) 0.0489(7) Uani 1 1 d . . . H28 H 0.1180 -1.0125 0.2883 0.059 Uiso 1 1 calc R . . C29 C 0.13663(7) -0.7513(4) 0.33875(9) 0.0526(7) Uani 1 1 d . . . H29 H 0.1622 -0.7838 0.3371 0.063 Uiso 1 1 calc R . . C30 C 0.12603(7) -0.5687(4) 0.37054(9) 0.0445(6) Uani 1 1 d . . . H30 H 0.1445 -0.4790 0.3906 0.053 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 N1 0.0366(12) 0.0326(10) 0.0387(11) -0.0033(8) 0.0130(9) -0.0065(9) N2 0.0416(12) 0.0363(10) 0.0541(13) -0.0148(9) 0.0232(11) -0.0120(9) N3 0.0353(12) 0.0376(10) 0.0511(12) -0.0127(9) 0.0138(10) -0.0087(9) N4 0.0310(11) 0.0309(10) 0.0392(11) -0.0019(8) 0.0066(9) -0.0037(8) N5 0.0375(12) 0.0330(10) 0.0505(12) -0.0076(9) 0.0146(10) -0.0024(9) N6 0.0344(12) 0.0315(9) 0.0448(12) -0.0069(9) 0.0126(10) -0.0043(8) N7 0.0350(12) 0.0314(10) 0.0385(11) 0.0010(9) 0.0061(9) -0.0040(8) N8 0.0350(12) 0.0396(11) 0.0608(14) -0.0132(10) 0.0111(10) -0.0068(9) N9 0.0322(11) 0.0371(10) 0.0486(12) -0.0095(9) 0.0044(10) -0.0047(9) C1 0.0336(14) 0.0292(11) 0.0380(13) -0.0016(10) 0.0073(11) -0.0030(10) C2 0.0367(14) 0.0385(13) 0.0500(15) -0.0138(11) 0.0065(12) -0.0084(11) C3 0.0311(13) 0.0307(11) 0.0333(13) -0.0004(10) 0.0047(11) -0.0012(10) C4 0.0335(13) 0.0329(12) 0.0366(13) 0.0015(10) 0.0085(11) -0.0019(10) C5 0.0339(13) 0.0292(11) 0.0326(12) 0.0008(10) 0.0013(11) 0.0036(10) C6 0.0408(14) 0.0362(12) 0.0379(13) -0.0004(11) 0.0035(12) -0.0007(11) C7 0.0539(17) 0.0397(13) 0.0409(15) -0.0088(11) 0.0004(13) 0.0035(12) C8 0.0499(17) 0.0536(15) 0.0437(15) -0.0081(13) 0.0109(13) 0.0102(13) C9 0.0457(16) 0.0549(15) 0.0492(15) -0.0049(13) 0.0165(13) -0.0010(13) C10 0.0399(15) 0.0405(13) 0.0418(14) -0.0064(11) 0.0095(12) -0.0032(11) C11 0.0300(13) 0.0309(12) 0.0338(13) 0.0004(10) 0.0050(11) 0.0026(10) C12 0.0320(13) 0.0350(12) 0.0429(14) 0.0000(11) 0.0116(12) -0.0045(10) C13 0.0326(13) 0.0276(11) 0.0324(12) 0.0024(9) 0.0038(11) 0.0006(10) C14 0.0360(14) 0.0275(11) 0.0386(14) -0.0027(10) 0.0056(12) -0.0020(10) C15 0.0365(14) 0.0302(11) 0.0340(13) 0.0022(10) 0.0065(11) 0.0034(10) C16 0.0394(15) 0.0412(13) 0.0474(15) -0.0056(11) 0.0094(12) 0.0039(11) C17 0.0438(16) 0.0529(15) 0.0526(16) -0.0047(13) 0.0139(14) 0.0081(13) C18 0.063(2) 0.0509(15) 0.0435(15) -0.0074(13) 0.0137(14) 0.0150(14) C19 0.0563(18) 0.0471(14) 0.0445(15) -0.0115(12) 0.0048(14) 0.0014(13) C20 0.0380(15) 0.0414(13) 0.0457(15) -0.0071(11) 0.0042(12) 0.0034(11) C21 0.0352(14) 0.0296(11) 0.0336(13) 0.0000(10) 0.0012(11) -0.0015(10) C22 0.0365(15) 0.0384(13) 0.0449(15) -0.0064(11) -0.0008(12) -0.0077(11) C23 0.0318(13) 0.0323(12) 0.0334(13) 0.0019(10) 0.0010(11) -0.0009(10) C24 0.0347(14) 0.0349(12) 0.0386(13) 0.0042(11) 0.0078(11) -0.0024(10) C25 0.0400(15) 0.0359(12) 0.0293(13) 0.0059(10) 0.0049(11) -0.0032(11) C26 0.0424(15) 0.0399(13) 0.0405(14) -0.0006(11) 0.0029(12) -0.0026(11) C27 0.0595(18) 0.0372(13) 0.0418(15) -0.0042(11) 0.0046(13) -0.0095(12) C28 0.0614(19) 0.0433(14) 0.0458(15) -0.0095(12) 0.0237(14) -0.0069(13) C29 0.0486(17) 0.0581(15) 0.0541(16) -0.0126(14) 0.0196(14) -0.0080(13) C30 0.0406(15) 0.0506(14) 0.0435(15) -0.0111(12) 0.0103(13) -0.0101(12) _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 C4 1.324(2) . ? N1 C1 1.355(3) . ? N2 C1 1.332(2) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 C2 1.328(3) . ? N3 C1 1.346(3) . ? N4 C14 1.337(2) . ? N4 C11 1.346(2) . ? N5 C11 1.349(2) . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? N6 C12 1.332(2) . ? N6 C11 1.342(2) . ? N7 C24 1.328(2) . ? N7 C21 1.354(3) . ? N8 C21 1.338(2) . ? N8 H8A 0.8800 . ? N8 H8B 0.8800 . ? N9 C22 1.331(3) . ? N9 C21 1.348(3) . ? C2 C3 1.395(3) . ? C2 H2 0.9500 . ? C3 C4 1.385(3) . ? C3 C5 1.476(3) . ? C4 H4 0.9500 . ? C5 C6 1.396(3) . ? C5 C10 1.398(3) . ? C6 C7 1.383(3) . ? C6 H6 0.9500 . ? C7 C8 1.379(3) . ? C7 H7 0.9500 . ? C8 C9 1.373(3) . ? C8 H8 0.9500 . ? C9 C10 1.381(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 C14 1.379(3) . ? C13 C15 1.484(3) . ? C14 H14 0.9500 . ? C15 C20 1.387(3) . ? C15 C16 1.393(3) . ? C16 C17 1.389(3) . ? C16 H16 0.9500 . ? C17 C18 1.371(3) . ? C17 H17 0.9500 . ? C18 C19 1.376(3) . ? C18 H18 0.9500 . ? C19 C20 1.388(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C22 C23 1.381(3) . ? C22 H22 0.9500 . ? C23 C24 1.391(3) . ? C23 C25 1.481(3) . ? C24 H24 0.9500 . ? C25 C30 1.392(3) . ? C25 C26 1.398(3) . ? C26 C27 1.385(3) . ? C26 H26 0.9500 . ? C27 C28 1.379(3) . ? C27 H27 0.9500 . ? C28 C29 1.375(3) . ? C28 H28 0.9500 . ? C29 C30 1.386(3) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? 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 C4 N1 C1 116.35(17) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C2 N3 C1 115.80(18) . . ? C14 N4 C11 115.73(18) . . ? C11 N5 H5A 120.0 . . ? C11 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C12 N6 C11 116.13(18) . . ? C24 N7 C21 115.39(18) . . ? C21 N8 H8A 120.0 . . ? C21 N8 H8B 120.0 . . ? H8A N8 H8B 120.0 . . ? C22 N9 C21 115.63(18) . . ? N2 C1 N3 118.50(19) . . ? N2 C1 N1 116.94(18) . . ? N3 C1 N1 124.56(19) . . ? N3 C2 C3 125.4(2) . . ? N3 C2 H2 117.3 . . ? C3 C2 H2 117.3 . . ? C4 C3 C2 112.81(19) . . ? C4 C3 C5 123.36(19) . . ? C2 C3 C5 123.84(19) . . ? N1 C4 C3 125.0(2) . . ? N1 C4 H4 117.5 . . ? C3 C4 H4 117.5 . . ? C6 C5 C10 116.6(2) . . ? C6 C5 C3 122.3(2) . . ? C10 C5 C3 121.04(19) . . ? C7 C6 C5 121.6(2) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 C7 C6 120.5(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C9 C8 C7 119.0(2) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C10 120.8(2) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C5 121.5(2) . . ? C9 C10 H10 119.2 . . ? C5 C10 H10 119.2 . . ? N6 C11 N4 125.08(18) . . ? N6 C11 N5 117.04(18) . . ? N4 C11 N5 117.86(19) . . ? N6 C12 C13 124.5(2) . . ? N6 C12 H12 117.7 . . ? C13 C12 H12 117.7 . . ? C14 C13 C12 113.80(19) . . ? C14 C13 C15 123.49(18) . . ? C12 C13 C15 122.70(19) . . ? N4 C14 C13 124.71(19) . . ? N4 C14 H14 117.6 . . ? C13 C14 H14 117.6 . . ? C20 C15 C16 117.8(2) . . ? C20 C15 C13 121.6(2) . . ? C16 C15 C13 120.6(2) . . ? C17 C16 C15 120.9(2) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C18 C17 C16 120.1(2) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 120.1(2) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C20 119.7(2) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C15 C20 C19 121.4(2) . . ? C15 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? N8 C21 N9 116.90(19) . . ? N8 C21 N7 117.70(19) . . ? N9 C21 N7 125.41(19) . . ? N9 C22 C23 125.0(2) . . ? N9 C22 H22 117.5 . . ? C23 C22 H22 117.5 . . ? C22 C23 C24 113.58(19) . . ? C22 C23 C25 122.6(2) . . ? C24 C23 C25 123.8(2) . . ? N7 C24 C23 125.0(2) . . ? N7 C24 H24 117.5 . . ? C23 C24 H24 117.5 . . ? C30 C25 C26 117.3(2) . . ? C30 C25 C23 121.3(2) . . ? C26 C25 C23 121.4(2) . . ? C27 C26 C25 121.4(2) . . ? C27 C26 H26 119.3 . . ? C25 C26 H26 119.3 . . ? C28 C27 C26 120.3(2) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C29 C28 C27 119.1(2) . . ? C29 C28 H28 120.4 . . ? C27 C28 H28 120.4 . . ? C28 C29 C30 120.8(2) . . ? C28 C29 H29 119.6 . . ? C30 C29 H29 119.6 . . ? C29 C30 C25 121.0(2) . . ? C29 C30 H30 119.5 . . ? C25 C30 H30 119.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.183 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.045 #============================================================================== data_compound5 _database_code_depnum_ccdc_archive 'CCDC 693052' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 N3' _chemical_formula_sum 'C14 H11 N3' _chemical_formula_weight 221.26 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' _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 7.7717(4) _cell_length_b 11.5440(7) _cell_length_c 13.2696(9) _cell_angle_alpha 71.552(3) _cell_angle_beta 89.896(4) _cell_angle_gamma 87.983(4) _cell_volume 1128.57(12) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 56710 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 25.028 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9763 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22623 _diffrn_reflns_av_R_equivalents 0.069 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3916 _reflns_number_gt 3227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1015P)^2^+0.4984P] 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 3916 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.1825 _refine_ls_wR_factor_gt 0.1732 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 N1 N 0.8638(2) 0.14920(18) 0.22325(15) 0.0360(5) Uani 1 1 d . . . N2 N 1.0231(2) 0.0968(2) 0.37774(15) 0.0436(5) Uani 1 1 d . . . H2A H 1.1217 0.0784 0.4126 0.052 Uiso 1 1 calc R . . H2B H 0.9265 0.0964 0.4125 0.052 Uiso 1 1 calc R . . N3 N 1.1704(2) 0.12496(18) 0.22090(15) 0.0362(5) Uani 1 1 d . . . N4 N 0.6700(2) 0.13651(17) 0.47853(15) 0.0348(5) Uani 1 1 d . . . N5 N 0.5226(2) 0.12193(19) 0.33258(15) 0.0398(5) Uani 1 1 d . . . H5A H 0.6212 0.1052 0.3066 0.048 Uiso 1 1 calc R . . H5B H 0.4263 0.1252 0.2969 0.048 Uiso 1 1 calc R . . N6 N 0.3624(2) 0.16667(18) 0.46190(15) 0.0364(5) Uani 1 1 d . . . C1 C 1.0200(3) 0.1251(2) 0.27237(18) 0.0331(5) Uani 1 1 d . . . C2 C 1.1611(3) 0.1551(2) 0.11593(18) 0.0344(5) Uani 1 1 d . . . H2 H 1.2653 0.1541 0.0786 0.041 Uiso 1 1 calc R . . C3 C 1.0094(3) 0.18820(19) 0.05657(17) 0.0324(5) Uani 1 1 d . . . C4 C 0.8628(3) 0.1818(2) 0.11819(18) 0.0356(5) Uani 1 1 d . . . H4 H 0.7547 0.2021 0.0825 0.043 Uiso 1 1 calc R . . C5 C 1.0036(3) 0.2230(2) -0.06059(17) 0.0328(5) Uani 1 1 d . . . C6 C 1.0657(3) 0.1421(2) -0.11078(18) 0.0363(5) Uani 1 1 d . . . H6 H 1.1151 0.0654 -0.0692 0.044 Uiso 1 1 calc R . . C7 C 1.0575(3) 0.1702(2) -0.22125(19) 0.0412(6) Uani 1 1 d . . . H7 H 1.1017 0.1129 -0.2536 0.049 Uiso 1 1 calc R . . C8 C 0.9865(3) 0.2791(2) -0.28274(19) 0.0422(6) Uani 1 1 d . . . H8 H 0.9802 0.2967 -0.3576 0.051 Uiso 1 1 calc R . . C9 C 0.9219(3) 0.3666(2) -0.23605(18) 0.0378(5) Uani 1 1 d . . . C10 C 0.8501(3) 0.4814(3) -0.2986(2) 0.0497(7) Uani 1 1 d . . . H10 H 0.8415 0.4996 -0.3735 0.060 Uiso 1 1 calc R . . C11 C 0.7933(4) 0.5659(3) -0.2533(2) 0.0549(7) Uani 1 1 d . . . H11 H 0.7450 0.6423 -0.2963 0.066 Uiso 1 1 calc R . . C12 C 0.8062(3) 0.5401(2) -0.1432(2) 0.0505(7) Uani 1 1 d . . . H12 H 0.7676 0.5998 -0.1120 0.061 Uiso 1 1 calc R . . C13 C 0.8733(3) 0.4306(2) -0.0800(2) 0.0428(6) Uani 1 1 d . . . H13 H 0.8811 0.4151 -0.0055 0.051 Uiso 1 1 calc R . . C14 C 0.9319(3) 0.3391(2) -0.12415(18) 0.0342(5) Uani 1 1 d . . . C15 C 0.5192(3) 0.1424(2) 0.42614(18) 0.0328(5) Uani 1 1 d . . . C16 C 0.3627(3) 0.1929(2) 0.55196(18) 0.0372(5) Uani 1 1 d . . . H16 H 0.2549 0.2116 0.5781 0.045 Uiso 1 1 calc R . . C17 C 0.5092(3) 0.1950(2) 0.61128(18) 0.0342(5) Uani 1 1 d . . . C18 C 0.6609(3) 0.1610(2) 0.56981(18) 0.0352(5) Uani 1 1 d . . . H18 H 0.7644 0.1549 0.6094 0.042 Uiso 1 1 calc R . . C19 C 0.5035(3) 0.2236(2) 0.71242(18) 0.0354(5) Uani 1 1 d . . . C20 C 0.5652(3) 0.1387(2) 0.80461(19) 0.0391(5) Uani 1 1 d . . . H20 H 0.6127 0.0627 0.8021 0.047 Uiso 1 1 calc R . . C21 C 0.5594(3) 0.1620(2) 0.90210(19) 0.0434(6) Uani 1 1 d . . . H21 H 0.6032 0.1022 0.9646 0.052 Uiso 1 1 calc R . . C22 C 0.4909(3) 0.2705(2) 0.90731(19) 0.0428(6) Uani 1 1 d . . . H22 H 0.4869 0.2854 0.9737 0.051 Uiso 1 1 calc R . . C23 C 0.4260(3) 0.3606(2) 0.81549(19) 0.0394(6) Uani 1 1 d . . . C24 C 0.3541(3) 0.4742(3) 0.8193(2) 0.0500(7) Uani 1 1 d . . . H24 H 0.3464 0.4890 0.8856 0.060 Uiso 1 1 calc R . . C25 C 0.2962(3) 0.5619(3) 0.7296(3) 0.0562(7) Uani 1 1 d . . . H25 H 0.2480 0.6371 0.7336 0.067 Uiso 1 1 calc R . . C26 C 0.3076(3) 0.5413(2) 0.6313(2) 0.0534(7) Uani 1 1 d . . . H26 H 0.2684 0.6032 0.5688 0.064 Uiso 1 1 calc R . . C27 C 0.3746(3) 0.4331(2) 0.6243(2) 0.0432(6) Uani 1 1 d . . . H27 H 0.3816 0.4209 0.5569 0.052 Uiso 1 1 calc R . . C28 C 0.4339(3) 0.3390(2) 0.71613(18) 0.0359(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 N1 0.0257(9) 0.0472(12) 0.0362(11) -0.0149(9) -0.0004(7) 0.0006(8) N2 0.0269(10) 0.0690(14) 0.0329(11) -0.0137(10) -0.0001(8) 0.0042(9) N3 0.0259(9) 0.0454(11) 0.0361(11) -0.0116(9) 0.0002(7) 0.0025(8) N4 0.0267(9) 0.0410(11) 0.0371(11) -0.0131(8) 0.0000(7) 0.0001(8) N5 0.0253(9) 0.0589(13) 0.0396(11) -0.0217(10) 0.0010(8) 0.0003(8) N6 0.0264(9) 0.0470(12) 0.0362(11) -0.0140(9) 0.0005(7) 0.0013(8) C1 0.0251(11) 0.0368(12) 0.0373(12) -0.0117(10) 0.0003(9) 0.0013(9) C2 0.0269(11) 0.0402(13) 0.0356(12) -0.0116(10) 0.0035(9) 0.0000(9) C3 0.0297(11) 0.0311(12) 0.0366(12) -0.0113(9) -0.0004(9) 0.0000(8) C4 0.0266(11) 0.0444(13) 0.0370(13) -0.0149(10) -0.0041(9) 0.0025(9) C5 0.0278(11) 0.0355(12) 0.0344(12) -0.0095(9) 0.0012(9) -0.0037(9) C6 0.0339(12) 0.0380(13) 0.0370(13) -0.0115(10) 0.0045(9) -0.0032(9) C7 0.0387(13) 0.0484(15) 0.0405(14) -0.0190(11) 0.0100(10) -0.0095(11) C8 0.0410(13) 0.0549(15) 0.0312(12) -0.0131(11) 0.0038(10) -0.0129(11) C9 0.0316(11) 0.0429(13) 0.0367(13) -0.0088(10) -0.0002(9) -0.0083(10) C10 0.0442(14) 0.0525(16) 0.0438(15) -0.0025(12) -0.0063(11) -0.0071(12) C11 0.0502(16) 0.0422(15) 0.0620(18) -0.0022(13) -0.0089(13) 0.0001(12) C12 0.0488(15) 0.0393(14) 0.0615(18) -0.0138(12) -0.0043(12) 0.0019(11) C13 0.0398(13) 0.0424(14) 0.0472(15) -0.0155(11) -0.0030(10) -0.0031(10) C14 0.0274(11) 0.0362(12) 0.0391(13) -0.0117(10) -0.0013(9) -0.0050(9) C15 0.0265(11) 0.0361(12) 0.0352(12) -0.0102(9) 0.0004(9) -0.0012(9) C16 0.0286(11) 0.0461(14) 0.0358(12) -0.0122(10) 0.0036(9) 0.0036(9) C17 0.0310(11) 0.0336(12) 0.0367(12) -0.0096(10) 0.0008(9) 0.0008(9) C18 0.0286(11) 0.0381(13) 0.0391(13) -0.0126(10) -0.0028(9) 0.0010(9) C19 0.0291(11) 0.0406(13) 0.0378(13) -0.0141(10) 0.0033(9) -0.0029(9) C20 0.0336(12) 0.0429(13) 0.0416(13) -0.0146(10) -0.0013(10) 0.0012(10) C21 0.0394(13) 0.0530(15) 0.0359(13) -0.0111(11) -0.0043(10) -0.0043(11) C22 0.0376(12) 0.0578(16) 0.0372(13) -0.0202(12) 0.0050(10) -0.0111(11) C23 0.0303(11) 0.0472(14) 0.0449(14) -0.0198(11) 0.0084(10) -0.0082(10) C24 0.0443(14) 0.0522(16) 0.0625(18) -0.0306(14) 0.0130(12) -0.0081(12) C25 0.0463(15) 0.0451(15) 0.083(2) -0.0287(15) 0.0128(14) -0.0030(12) C26 0.0507(15) 0.0381(14) 0.0666(19) -0.0102(13) 0.0035(13) 0.0002(11) C27 0.0436(13) 0.0395(14) 0.0456(14) -0.0119(11) 0.0063(11) -0.0036(10) C28 0.0275(11) 0.0389(13) 0.0413(13) -0.0125(10) 0.0053(9) -0.0049(9) _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 C4 1.324(3) . ? N1 C1 1.357(3) . ? N2 C1 1.331(3) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 C2 1.326(3) . ? N3 C1 1.353(3) . ? N4 C18 1.329(3) . ? N4 C15 1.352(3) . ? N5 C15 1.335(3) . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? N6 C16 1.322(3) . ? N6 C15 1.359(3) . ? C2 C3 1.392(3) . ? C2 H2 0.9500 . ? C3 C4 1.392(3) . ? C3 C5 1.478(3) . ? C4 H4 0.9500 . ? C5 C6 1.382(3) . ? C5 C14 1.432(3) . ? C6 C7 1.399(3) . ? C6 H6 0.9500 . ? C7 C8 1.361(4) . ? C7 H7 0.9500 . ? C8 C9 1.420(4) . ? C8 H8 0.9500 . ? C9 C10 1.418(3) . ? C9 C14 1.418(3) . ? C10 C11 1.359(4) . ? C10 H10 0.9500 . ? C11 C12 1.399(4) . ? C11 H11 0.9500 . ? C12 C13 1.363(4) . ? C12 H12 0.9500 . ? C13 C14 1.422(3) . ? C13 H13 0.9500 . ? C16 C17 1.391(3) . ? C16 H16 0.9500 . ? C17 C18 1.396(3) . ? C17 C19 1.480(3) . ? C18 H18 0.9500 . ? C19 C20 1.377(3) . ? C19 C28 1.436(3) . ? C20 C21 1.402(3) . ? C20 H20 0.9500 . ? C21 C22 1.365(4) . ? C21 H21 0.9500 . ? C22 C23 1.409(4) . ? C22 H22 0.9500 . ? C23 C28 1.418(3) . ? C23 C24 1.423(4) . ? C24 C25 1.361(4) . ? C24 H24 0.9500 . ? C25 C26 1.400(4) . ? C25 H25 0.9500 . ? C26 C27 1.367(4) . ? C26 H26 0.9500 . ? C27 C28 1.416(3) . ? C27 H27 0.9500 . ? 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 C4 N1 C1 116.79(18) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C2 N3 C1 116.60(18) . . ? C18 N4 C15 116.09(18) . . ? C15 N5 H5A 120.0 . . ? C15 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C16 N6 C15 115.92(18) . . ? N2 C1 N3 118.78(19) . . ? N2 C1 N1 117.34(19) . . ? N3 C1 N1 123.9(2) . . ? N3 C2 C3 124.59(19) . . ? N3 C2 H2 117.7 . . ? C3 C2 H2 117.7 . . ? C4 C3 C2 113.6(2) . . ? C4 C3 C5 123.05(19) . . ? C2 C3 C5 123.31(19) . . ? N1 C4 C3 124.39(19) . . ? N1 C4 H4 117.8 . . ? C3 C4 H4 117.8 . . ? C6 C5 C14 118.7(2) . . ? C6 C5 C3 120.0(2) . . ? C14 C5 C3 121.31(19) . . ? C5 C6 C7 121.6(2) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C8 C7 C6 120.4(2) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 120.6(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C14 119.3(2) . . ? C10 C9 C8 121.6(2) . . ? C14 C9 C8 119.1(2) . . ? C11 C10 C9 121.1(3) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 119.8(2) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C13 C12 C11 121.0(3) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 121.0(2) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C9 C14 C13 117.9(2) . . ? C9 C14 C5 119.4(2) . . ? C13 C14 C5 122.7(2) . . ? N5 C15 N4 118.23(19) . . ? N5 C15 N6 116.87(19) . . ? N4 C15 N6 124.9(2) . . ? N6 C16 C17 124.8(2) . . ? N6 C16 H16 117.6 . . ? C17 C16 H16 117.6 . . ? C16 C17 C18 113.8(2) . . ? C16 C17 C19 123.05(19) . . ? C18 C17 C19 123.1(2) . . ? N4 C18 C17 124.3(2) . . ? N4 C18 H18 117.9 . . ? C17 C18 H18 117.9 . . ? C20 C19 C28 119.2(2) . . ? C20 C19 C17 120.0(2) . . ? C28 C19 C17 120.9(2) . . ? C19 C20 C21 121.5(2) . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? C22 C21 C20 120.1(2) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 120.9(2) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C22 C23 C28 119.6(2) . . ? C22 C23 C24 121.7(2) . . ? C28 C23 C24 118.7(2) . . ? C25 C24 C23 121.2(3) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C24 C25 C26 119.9(3) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C27 C26 C25 120.7(3) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C26 C27 C28 121.0(3) . . ? C26 C27 H27 119.5 . . ? C28 C27 H27 119.5 . . ? C27 C28 C23 118.4(2) . . ? C27 C28 C19 122.7(2) . . ? C23 C28 C19 118.8(2) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.265 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.069 #============================================================================== data_compound6 _database_code_depnum_ccdc_archive 'CCDC 693053' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 N3' _chemical_formula_sum 'C14 H11 N3' _chemical_formula_weight 221.26 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 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' _cell_length_a 46.0671(8) _cell_length_b 6.28130(10) _cell_length_c 7.4605(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.0684(13) _cell_angle_gamma 90.00 _cell_volume 2146.68(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 27468 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9751 _exptl_absorpt_correction_T_max 0.9850 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17712 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -63 _diffrn_reflns_limit_h_max 64 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 29.99 _reflns_number_total 3117 _reflns_number_gt 2927 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0549P)^2^+0.4062P] 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 3117 _refine_ls_number_parameters 307 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0867 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 N1 N 0.00992(3) 0.6891(2) 0.17266(18) 0.0178(3) Uani 1 1 d . . . N2 N 0.03833(3) 0.4087(2) 0.09862(19) 0.0199(3) Uani 1 1 d . . . H2A H 0.0418 0.2715 0.0893 0.024 Uiso 1 1 calc R . . H2B H 0.0512 0.5020 0.0680 0.024 Uiso 1 1 calc R . . N3 N -0.00549(3) 0.3253(2) 0.20467(19) 0.0180(3) Uani 1 1 d . . . N4 N 0.09569(3) -0.0832(2) 0.43525(19) 0.0197(3) Uani 1 1 d . . . N5 N 0.04736(3) 0.0185(2) 0.3864(2) 0.0204(3) Uani 1 1 d . . . H5A H 0.0430 -0.1123 0.3510 0.025 Uiso 1 1 calc R . . H5B H 0.0335 0.1149 0.3872 0.025 Uiso 1 1 calc R . . N6 N 0.08078(3) 0.2738(2) 0.49529(19) 0.0198(3) Uani 1 1 d . . . C1 C 0.01363(3) 0.4753(3) 0.1592(2) 0.0165(3) Uani 1 1 d . . . C2 C -0.01547(3) 0.7535(3) 0.2240(2) 0.0172(3) Uani 1 1 d . . . H2 H -0.0187 0.9021 0.2346 0.021 Uiso 1 1 calc R . . C3 C -0.03770(3) 0.6140(3) 0.2635(2) 0.0160(3) Uani 1 1 d . . . C4 C -0.03063(3) 0.3982(3) 0.2543(2) 0.0175(3) Uani 1 1 d . . . H4 H -0.0446 0.2971 0.2853 0.021 Uiso 1 1 calc R . . C5 C -0.06619(3) 0.6888(3) 0.3108(2) 0.0158(3) Uani 1 1 d . . . C6 C -0.06843(4) 0.8842(3) 0.4059(2) 0.0181(3) Uani 1 1 d . . . H6 H -0.0512 0.9613 0.4451 0.022 Uiso 1 1 calc R . . C7 C -0.09498(4) 0.9630(3) 0.4418(2) 0.0189(3) Uani 1 1 d . . . H7 H -0.0958 1.0942 0.5043 0.023 Uiso 1 1 calc R . . C8 C -0.12118(4) 0.8511(3) 0.3867(2) 0.0177(3) Uani 1 1 d . . . C9 C -0.14901(4) 0.9288(3) 0.4204(2) 0.0213(3) Uani 1 1 d . . . H9 H -0.1505 1.0609 0.4807 0.026 Uiso 1 1 calc R . . C10 C -0.17382(4) 0.8141(3) 0.3662(2) 0.0235(3) Uani 1 1 d . . . H10 H -0.1924 0.8673 0.3896 0.028 Uiso 1 1 calc R . . C11 C -0.17192(4) 0.6174(3) 0.2758(2) 0.0229(3) Uani 1 1 d . . . H11 H -0.1892 0.5399 0.2383 0.028 Uiso 1 1 calc R . . C12 C -0.14535(4) 0.5377(3) 0.2419(2) 0.0202(3) Uani 1 1 d . . . H12 H -0.1443 0.4052 0.1815 0.024 Uiso 1 1 calc R . . C13 C -0.11925(4) 0.6521(3) 0.2967(2) 0.0170(3) Uani 1 1 d . . . C14 C -0.09150(4) 0.5757(3) 0.2594(2) 0.0170(3) Uani 1 1 d . . . H14 H -0.0903 0.4441 0.1978 0.020 Uiso 1 1 calc R . . C15 C 0.07547(4) 0.0715(3) 0.4395(2) 0.0176(3) Uani 1 1 d . . . C16 C 0.10859(4) 0.3233(3) 0.5471(2) 0.0193(3) Uani 1 1 d . . . H16 H 0.1130 0.4645 0.5869 0.023 Uiso 1 1 calc R . . C17 C 0.13150(3) 0.1791(3) 0.5458(2) 0.0172(3) Uani 1 1 d . . . C18 C 0.12307(4) -0.0254(3) 0.4882(2) 0.0202(3) Uani 1 1 d . . . H18 H 0.1379 -0.1305 0.4866 0.024 Uiso 1 1 calc R . . C19 C 0.16213(3) 0.2338(3) 0.6072(2) 0.0167(3) Uani 1 1 d . . . C20 C 0.17376(4) 0.4360(3) 0.5665(2) 0.0183(3) Uani 1 1 d . . . H20 H 0.1617 0.5352 0.4972 0.022 Uiso 1 1 calc R . . C21 C 0.20202(4) 0.4904(3) 0.6254(2) 0.0180(3) Uani 1 1 d . . . H21 H 0.2091 0.6274 0.5982 0.022 Uiso 1 1 calc R . . C22 C 0.22075(4) 0.3447(3) 0.7264(2) 0.0174(3) Uani 1 1 d . . . C23 C 0.25020(4) 0.3942(3) 0.7877(2) 0.0199(3) Uani 1 1 d . . . H23 H 0.2580 0.5290 0.7604 0.024 Uiso 1 1 calc R . . C24 C 0.26757(4) 0.2492(3) 0.8862(2) 0.0224(3) Uani 1 1 d . . . H24 H 0.2872 0.2847 0.9274 0.027 Uiso 1 1 calc R . . C25 C 0.25636(4) 0.0466(3) 0.9267(2) 0.0210(3) Uani 1 1 d . . . H25 H 0.2685 -0.0527 0.9954 0.025 Uiso 1 1 calc R . . C26 C 0.22803(4) -0.0068(3) 0.8670(2) 0.0183(3) Uani 1 1 d . . . H26 H 0.2208 -0.1436 0.8934 0.022 Uiso 1 1 calc R . . C27 C 0.20957(3) 0.1409(3) 0.7664(2) 0.0167(3) Uani 1 1 d . . . C28 C 0.18018(4) 0.0907(3) 0.7063(2) 0.0172(3) Uani 1 1 d . . . H28 H 0.1727 -0.0446 0.7348 0.021 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 N1 0.0171(6) 0.0153(6) 0.0210(6) -0.0004(5) 0.0018(5) -0.0007(5) N2 0.0198(6) 0.0159(6) 0.0247(6) 0.0004(5) 0.0056(5) -0.0001(5) N3 0.0200(6) 0.0143(6) 0.0198(6) 0.0002(5) 0.0023(5) -0.0009(5) N4 0.0200(7) 0.0156(7) 0.0237(7) -0.0028(5) 0.0028(5) -0.0011(5) N5 0.0191(7) 0.0146(6) 0.0272(7) -0.0009(5) 0.0002(5) -0.0014(5) N6 0.0181(6) 0.0162(6) 0.0249(7) -0.0008(5) 0.0017(5) 0.0010(5) C1 0.0175(7) 0.0162(7) 0.0152(6) 0.0006(5) -0.0006(5) 0.0002(6) C2 0.0176(7) 0.0142(7) 0.0194(7) -0.0005(5) -0.0001(5) 0.0002(5) C3 0.0169(7) 0.0150(7) 0.0159(7) 0.0004(5) 0.0001(5) 0.0007(6) C4 0.0197(7) 0.0147(7) 0.0179(7) 0.0000(5) 0.0013(6) -0.0016(6) C5 0.0176(7) 0.0141(7) 0.0158(7) 0.0006(5) 0.0019(5) 0.0010(5) C6 0.0189(7) 0.0164(7) 0.0187(7) -0.0005(6) 0.0007(6) -0.0007(6) C7 0.0238(8) 0.0148(7) 0.0179(7) -0.0018(6) 0.0009(6) -0.0001(6) C8 0.0195(7) 0.0178(8) 0.0157(6) 0.0002(6) 0.0013(5) 0.0028(6) C9 0.0222(8) 0.0205(8) 0.0213(7) 0.0008(6) 0.0029(6) 0.0048(6) C10 0.0181(7) 0.0263(9) 0.0259(8) 0.0017(7) 0.0021(6) 0.0043(7) C11 0.0178(7) 0.0273(9) 0.0234(7) 0.0006(7) 0.0003(6) -0.0020(7) C12 0.0190(7) 0.0222(8) 0.0193(7) -0.0013(6) 0.0010(6) -0.0020(6) C13 0.0175(7) 0.0178(7) 0.0156(6) 0.0015(6) 0.0011(5) -0.0010(6) C14 0.0193(7) 0.0155(7) 0.0161(6) -0.0011(5) 0.0017(5) -0.0001(6) C15 0.0187(7) 0.0167(7) 0.0176(7) 0.0019(6) 0.0029(5) -0.0001(6) C16 0.0185(7) 0.0159(7) 0.0230(7) -0.0020(6) 0.0007(6) 0.0005(6) C17 0.0158(7) 0.0182(7) 0.0176(7) 0.0000(5) 0.0028(5) 0.0000(6) C18 0.0186(7) 0.0174(8) 0.0248(8) -0.0012(6) 0.0033(6) 0.0024(6) C19 0.0166(7) 0.0167(7) 0.0172(7) -0.0017(6) 0.0033(5) 0.0001(6) C20 0.0207(7) 0.0166(7) 0.0177(7) 0.0003(6) 0.0025(5) 0.0020(6) C21 0.0216(8) 0.0151(7) 0.0179(7) 0.0005(6) 0.0044(6) -0.0012(6) C22 0.0204(7) 0.0178(7) 0.0144(6) -0.0006(5) 0.0036(5) -0.0007(6) C23 0.0202(8) 0.0200(8) 0.0197(7) -0.0017(6) 0.0033(6) -0.0021(6) C24 0.0183(8) 0.0258(9) 0.0226(8) -0.0020(7) -0.0004(6) -0.0020(6) C25 0.0215(8) 0.0223(8) 0.0187(7) 0.0008(6) 0.0004(6) 0.0014(7) C26 0.0222(8) 0.0178(7) 0.0150(7) 0.0011(5) 0.0019(6) 0.0010(6) C27 0.0183(7) 0.0176(7) 0.0146(6) -0.0007(6) 0.0040(5) 0.0005(6) C28 0.0179(7) 0.0160(7) 0.0181(7) 0.0007(6) 0.0040(5) -0.0009(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 N1 C2 1.332(2) . ? N1 C1 1.359(2) . ? N2 C1 1.335(2) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 C4 1.333(2) . ? N3 C1 1.357(2) . ? N4 C18 1.332(2) . ? N4 C15 1.349(2) . ? N5 C15 1.355(2) . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? N6 C16 1.335(2) . ? N6 C15 1.351(2) . ? C2 C3 1.402(2) . ? C2 H2 0.9500 . ? C3 C4 1.397(2) . ? C3 C5 1.472(2) . ? C4 H4 0.9500 . ? C5 C14 1.384(2) . ? C5 C6 1.427(2) . ? C6 C7 1.372(2) . ? C6 H6 0.9500 . ? C7 C8 1.420(2) . ? C7 H7 0.9500 . ? C8 C9 1.418(2) . ? C8 C13 1.426(2) . ? C9 C10 1.375(3) . ? C9 H9 0.9500 . ? C10 C11 1.415(3) . ? C10 H10 0.9500 . ? C11 C12 1.371(2) . ? C11 H11 0.9500 . ? C12 C13 1.423(2) . ? C12 H12 0.9500 . ? C13 C14 1.420(2) . ? C14 H14 0.9500 . ? C16 C17 1.392(2) . ? C16 H16 0.9500 . ? C17 C18 1.397(2) . ? C17 C19 1.477(2) . ? C18 H18 0.9500 . ? C19 C28 1.385(2) . ? C19 C20 1.423(2) . ? C20 C21 1.373(2) . ? C20 H20 0.9500 . ? C21 C22 1.418(2) . ? C21 H21 0.9500 . ? C22 C23 1.420(2) . ? C22 C27 1.423(2) . ? C23 C24 1.373(3) . ? C23 H23 0.9500 . ? C24 C25 1.418(3) . ? C24 H24 0.9500 . ? C25 C26 1.375(2) . ? C25 H25 0.9500 . ? C26 C27 1.419(2) . ? C26 H26 0.9500 . ? C27 C28 1.416(2) . ? C28 H28 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C1 116.28(14) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C4 N3 C1 115.86(14) . . ? C18 N4 C15 115.56(15) . . ? C15 N5 H5A 120.0 . . ? C15 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C16 N6 C15 116.43(14) . . ? N2 C1 N3 117.76(15) . . ? N2 C1 N1 116.94(14) . . ? N3 C1 N1 125.29(15) . . ? N1 C2 C3 123.60(15) . . ? N1 C2 H2 118.2 . . ? C3 C2 H2 118.2 . . ? C4 C3 C2 114.63(14) . . ? C4 C3 C5 122.66(14) . . ? C2 C3 C5 122.71(15) . . ? N3 C4 C3 124.10(14) . . ? N3 C4 H4 117.9 . . ? C3 C4 H4 117.9 . . ? C14 C5 C6 118.43(14) . . ? C14 C5 C3 121.08(14) . . ? C6 C5 C3 120.45(14) . . ? C7 C6 C5 121.34(15) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C6 C7 C8 120.89(15) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C9 C8 C7 122.36(16) . . ? C9 C8 C13 119.16(15) . . ? C7 C8 C13 118.47(14) . . ? C10 C9 C8 120.44(17) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.39(16) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 120.58(16) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 120.40(16) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 121.55(15) . . ? C14 C13 C8 119.40(14) . . ? C12 C13 C8 119.03(14) . . ? C5 C14 C13 121.42(15) . . ? C5 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? N4 C15 N6 125.58(14) . . ? N4 C15 N5 117.19(15) . . ? N6 C15 N5 117.22(14) . . ? N6 C16 C17 123.48(15) . . ? N6 C16 H16 118.3 . . ? C17 C16 H16 118.3 . . ? C16 C17 C18 114.47(14) . . ? C16 C17 C19 123.15(14) . . ? C18 C17 C19 122.33(15) . . ? N4 C18 C17 124.46(15) . . ? N4 C18 H18 117.8 . . ? C17 C18 H18 117.8 . . ? C28 C19 C20 118.34(15) . . ? C28 C19 C17 120.98(15) . . ? C20 C19 C17 120.68(15) . . ? C21 C20 C19 121.31(15) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C20 C21 C22 120.82(15) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C21 C22 C23 122.46(15) . . ? C21 C22 C27 118.59(14) . . ? C23 C22 C27 118.95(15) . . ? C24 C23 C22 120.68(16) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 120.30(16) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C26 C25 C24 120.31(16) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C27 120.45(16) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C28 C27 C26 121.40(15) . . ? C28 C27 C22 119.30(14) . . ? C26 C27 C22 119.30(14) . . ? C19 C28 C27 121.64(15) . . ? C19 C28 H28 119.2 . . ? C27 C28 H28 119.2 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.247 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.040 #============================================================================== data_compound4+HBF _database_code_depnum_ccdc_archive 'CCDC 693054' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '1.5(C6 F6), (C10 H9 N3)' _chemical_formula_sum 'C19 H9 F9 N3' _chemical_formula_weight 450.29 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/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 12.6457(9) _cell_length_b 7.7132(6) _cell_length_c 37.641(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.728(2) _cell_angle_gamma 90.00 _cell_volume 3638.1(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 21953 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 25.028 _exptl_crystal_description plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1800 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9524 _exptl_absorpt_correction_T_max 0.9870 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8087 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2873 _reflns_number_gt 2478 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0211P)^2^+18.8062P] 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 2873 _refine_ls_number_parameters 300 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1407 _refine_ls_wR_factor_gt 0.1356 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _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 F1 F 0.48203(18) 0.3710(3) 0.14878(6) 0.0429(6) Uani 1 1 d . . . F2 F 0.62430(18) 0.5718(3) 0.11956(6) 0.0434(6) Uani 1 1 d . . . F3 F 0.64665(17) 0.5370(3) 0.04909(6) 0.0411(6) Uani 1 1 d . . . F4 F 0.52427(18) 0.3038(3) 0.00783(5) 0.0419(6) Uani 1 1 d . . . F5 F 0.38154(19) 0.1047(3) 0.03703(6) 0.0484(6) Uani 1 1 d . . . F6 F 0.36047(17) 0.1363(3) 0.10773(6) 0.0443(6) Uani 1 1 d . . . N1 N 0.7403(2) -0.0635(4) 0.20450(7) 0.0218(6) Uani 1 1 d . . . N2 N 0.7509(2) 0.0934(4) 0.25698(7) 0.0244(6) Uani 1 1 d . . . H2A H 0.7491 -0.0048 0.2688 0.029 Uiso 1 1 calc R . . H2B H 0.7552 0.1925 0.2687 0.029 Uiso 1 1 calc R . . N3 N 0.7495(2) 0.2471(4) 0.20451(7) 0.0223(6) Uani 1 1 d . . . C1 C 0.7469(2) 0.0921(4) 0.22107(8) 0.0214(7) Uani 1 1 d . . . C2 C 0.7480(2) 0.2418(5) 0.16895(8) 0.0226(7) Uani 1 1 d . . . H2 H 0.7502 0.3486 0.1565 0.027 Uiso 1 1 calc R . . C3 C 0.7434(2) 0.0887(4) 0.14907(8) 0.0212(7) Uani 1 1 d . . . C4 C 0.7383(2) -0.0605(5) 0.16910(8) 0.0225(7) Uani 1 1 d . . . H4 H 0.7331 -0.1682 0.1567 0.027 Uiso 1 1 calc R . . C5 C 0.7466(3) 0.0867(4) 0.11000(8) 0.0218(7) Uani 1 1 d . . . C6 C 0.8151(3) 0.1963(5) 0.09431(9) 0.0268(8) Uani 1 1 d . . . H6 H 0.8589 0.2759 0.1089 0.032 Uiso 1 1 calc R . . C7 C 0.8201(3) 0.1903(5) 0.05755(9) 0.0305(8) Uani 1 1 d . . . H7 H 0.8668 0.2660 0.0472 0.037 Uiso 1 1 calc R . . C8 C 0.7572(3) 0.0745(5) 0.03625(9) 0.0319(9) Uani 1 1 d . . . H8 H 0.7613 0.0694 0.0113 0.038 Uiso 1 1 calc R . . C9 C 0.6884(3) -0.0343(5) 0.05119(9) 0.0310(8) Uani 1 1 d . . . H9 H 0.6450 -0.1135 0.0364 0.037 Uiso 1 1 calc R . . C10 C 0.6824(3) -0.0286(5) 0.08776(9) 0.0271(8) Uani 1 1 d . . . H10 H 0.6344 -0.1032 0.0978 0.033 Uiso 1 1 calc R . . C11 C 0.4927(3) 0.3523(5) 0.11433(9) 0.0289(8) Uani 1 1 d . . . C12 C 0.5649(3) 0.4542(5) 0.09923(10) 0.0296(8) Uani 1 1 d . . . C13 C 0.5765(3) 0.4382(5) 0.06367(10) 0.0284(8) Uani 1 1 d . . . C14 C 0.5145(3) 0.3206(5) 0.04273(9) 0.0291(8) Uani 1 1 d . . . C15 C 0.4415(3) 0.2203(5) 0.05759(10) 0.0319(8) Uani 1 1 d . . . C16 C 0.4313(3) 0.2352(5) 0.09325(10) 0.0283(8) Uani 1 1 d . . . F7A F 0.4939(5) 1.1773(11) 0.2136(3) 0.0360(18) Uiso 0.347(4) 1 d P A 1 F8A F 0.4869(5) 0.8738(13) 0.17759(17) 0.0271(15) Uiso 0.347(4) 1 d P A 1 F9A F 0.4931(5) 0.5657(10) 0.2132(2) 0.0329(17) Uiso 0.347(4) 1 d P A 1 C17A C 0.4951(13) 1.040(2) 0.2317(5) 0.021(5) Uiso 0.347(4) 1 d P . 1 C18A C 0.4947(12) 0.871(3) 0.2161(5) 0.018(5) Uiso 0.347(4) 1 d P A 1 C19A C 0.4980(13) 0.704(2) 0.2313(5) 0.019(5) Uiso 0.347(4) 1 d P . 1 F7B F 0.4943(7) 1.2091(12) 0.2291(3) 0.053(3) Uiso 0.3263(19) 1 d P B -2 F8B F 0.4896(6) 0.9597(13) 0.1786(2) 0.049(2) Uiso 0.3263(19) 1 d P B -2 F9B F 0.4983(6) 0.6196(12) 0.1993(2) 0.048(2) Uiso 0.3263(19) 1 d P B -2 F10B F 0.5056(6) 0.5306(10) 0.2704(2) 0.045(2) Uiso 0.3263(19) 1 d P B -3 F11B F 0.5058(6) 0.7865(12) 0.3199(2) 0.041(2) Uiso 0.3263(19) 1 d P B -3 F12B F 0.5036(6) 1.1233(12) 0.2998(2) 0.047(2) Uiso 0.3263(19) 1 d P B -3 C17B C 0.4997(16) 1.0365(19) 0.2411(5) 0.029(6) Uiso 0.3263(19) 1 d P B -2 C18B C 0.4936(11) 0.920(3) 0.2115(5) 0.028(5) Uiso 0.3263(19) 1 d P B -2 C19B C 0.4982(10) 0.751(3) 0.2246(4) 0.019(4) Uiso 0.3263(19) 1 d P B -2 C20B C 0.5028(15) 0.7036(18) 0.2585(5) 0.028(5) Uiso 0.3263(19) 1 d P B -3 C21B C 0.5009(12) 0.824(3) 0.2871(5) 0.026(5) Uiso 0.3263(19) 1 d P B -3 C22B C 0.5018(9) 0.988(2) 0.2745(4) 0.017(3) Uiso 0.3263(19) 1 d P B -3 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 F1 0.0516(14) 0.0503(15) 0.0281(11) -0.0010(11) 0.0104(10) 0.0063(12) F2 0.0437(13) 0.0381(13) 0.0446(13) -0.0042(11) -0.0082(10) -0.0102(11) F3 0.0333(12) 0.0409(13) 0.0499(14) 0.0133(11) 0.0085(10) -0.0084(10) F4 0.0531(14) 0.0481(15) 0.0257(11) 0.0028(10) 0.0100(10) 0.0013(11) F5 0.0548(15) 0.0448(15) 0.0435(14) -0.0074(12) -0.0012(11) -0.0198(12) F6 0.0393(13) 0.0457(14) 0.0506(14) 0.0109(12) 0.0158(10) -0.0114(11) N1 0.0228(14) 0.0229(15) 0.0200(14) 0.0009(12) 0.0040(11) -0.0006(12) N2 0.0308(15) 0.0236(16) 0.0190(14) 0.0000(12) 0.0040(11) -0.0029(13) N3 0.0207(14) 0.0248(16) 0.0214(14) 0.0011(12) 0.0029(11) 0.0004(12) C1 0.0175(16) 0.0253(19) 0.0214(16) 0.0000(14) 0.0027(12) -0.0026(14) C2 0.0190(17) 0.0252(19) 0.0234(17) 0.0046(14) 0.0023(12) 0.0000(14) C3 0.0211(17) 0.0237(18) 0.0192(16) 0.0001(14) 0.0044(12) 0.0001(14) C4 0.0206(17) 0.0252(19) 0.0214(16) -0.0015(14) 0.0026(13) -0.0016(14) C5 0.0246(18) 0.0201(18) 0.0210(16) 0.0009(14) 0.0038(13) 0.0044(14) C6 0.0307(19) 0.0257(19) 0.0242(17) 0.0007(15) 0.0046(14) -0.0003(15) C7 0.039(2) 0.028(2) 0.0262(18) 0.0081(15) 0.0124(15) 0.0028(17) C8 0.046(2) 0.030(2) 0.0205(17) 0.0033(15) 0.0063(15) 0.0081(18) C9 0.042(2) 0.027(2) 0.0222(18) -0.0023(15) -0.0018(15) 0.0021(17) C10 0.0292(19) 0.027(2) 0.0249(18) 0.0016(15) 0.0024(14) -0.0004(15) C11 0.0290(19) 0.034(2) 0.0247(17) 0.0032(16) 0.0062(14) 0.0047(16) C12 0.0287(19) 0.0229(19) 0.035(2) -0.0020(15) -0.0033(15) -0.0013(15) C13 0.0214(18) 0.028(2) 0.036(2) 0.0073(16) 0.0048(14) -0.0003(15) C14 0.031(2) 0.029(2) 0.0276(19) 0.0032(16) 0.0048(14) 0.0048(16) C15 0.033(2) 0.029(2) 0.0325(19) -0.0016(16) -0.0020(15) -0.0049(16) C16 0.0226(18) 0.028(2) 0.036(2) 0.0050(16) 0.0080(14) -0.0006(15) _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 F1 C11 1.329(4) . ? F2 C12 1.348(4) . ? F3 C13 1.341(4) . ? F4 C14 1.342(4) . ? F5 C15 1.346(4) . ? F6 C16 1.346(4) . ? N1 C4 1.330(4) . ? N1 C1 1.350(4) . ? N2 C1 1.346(4) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 C2 1.337(4) . ? N3 C1 1.351(4) . ? C2 C3 1.395(5) . ? C2 H2 0.9500 . ? C3 C4 1.382(5) . ? C3 C5 1.477(4) . ? C4 H4 0.9500 . ? C5 C6 1.397(5) . ? C5 C10 1.403(5) . ? C6 C7 1.394(5) . ? C6 H6 0.9500 . ? C7 C8 1.379(5) . ? C7 H7 0.9500 . ? C8 C9 1.382(5) . ? C8 H8 0.9500 . ? C9 C10 1.389(5) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.372(5) . ? C11 C12 1.384(5) . ? C12 C13 1.372(5) . ? C13 C14 1.376(5) . ? C14 C15 1.379(5) . ? C15 C16 1.371(5) . ? F7A C17A 1.260(17) . ? F8A C18A 1.440(19) . ? F9A C19A 1.266(17) . ? C17A C17A 1.37(4) 2_655 ? C17A C18A 1.43(3) . ? C18A C19A 1.40(3) . ? C19A C19A 1.40(3) 2_655 ? F7B C17B 1.404(17) . ? F8B C18B 1.269(18) . ? F9B C19B 1.394(17) . ? F10B C20B 1.406(15) . ? F11B C21B 1.261(18) . ? F12B C22B 1.412(16) . ? C17B C22B 1.31(2) . ? C17B C18B 1.42(2) . ? C18B C19B 1.39(2) . ? C19B C20B 1.32(2) . ? C20B C21B 1.43(2) . ? C21B C22B 1.35(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 C1 116.1(3) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C2 N3 C1 115.9(3) . . ? N2 C1 N1 117.6(3) . . ? N2 C1 N3 117.2(3) . . ? N1 C1 N3 125.3(3) . . ? N3 C2 C3 123.8(3) . . ? N3 C2 H2 118.1 . . ? C3 C2 H2 118.1 . . ? C4 C3 C2 114.5(3) . . ? C4 C3 C5 123.0(3) . . ? C2 C3 C5 122.5(3) . . ? N1 C4 C3 124.4(3) . . ? N1 C4 H4 117.8 . . ? C3 C4 H4 117.8 . . ? C6 C5 C10 118.3(3) . . ? C6 C5 C3 121.1(3) . . ? C10 C5 C3 120.6(3) . . ? C7 C6 C5 120.8(3) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C8 C7 C6 119.9(3) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.2(3) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C10 120.3(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C5 120.5(3) . . ? C9 C10 H10 119.8 . . ? C5 C10 H10 119.8 . . ? F1 C11 C16 120.8(3) . . ? F1 C11 C12 119.9(3) . . ? C16 C11 C12 119.3(3) . . ? F2 C12 C13 119.3(3) . . ? F2 C12 C11 119.8(3) . . ? C13 C12 C11 120.9(3) . . ? F3 C13 C12 120.8(3) . . ? F3 C13 C14 119.9(3) . . ? C12 C13 C14 119.4(3) . . ? F4 C14 C13 120.2(3) . . ? F4 C14 C15 119.9(3) . . ? C13 C14 C15 119.9(3) . . ? F5 C15 C16 119.9(3) . . ? F5 C15 C14 119.6(3) . . ? C16 C15 C14 120.4(3) . . ? F6 C16 C15 120.3(3) . . ? F6 C16 C11 119.7(3) . . ? C15 C16 C11 120.1(3) . . ? F7A C17A C17A 122.4(10) . 2_655 ? F7A C17A C18A 123.3(17) . . ? C17A C17A C18A 114.1(11) 2_655 . ? C19A C18A C17A 132.0(16) . . ? C19A C18A F8A 114.9(19) . . ? C17A C18A F8A 113.2(19) . . ? F9A C19A C19A 122.4(10) . 2_655 ? F9A C19A C18A 123.7(17) . . ? C19A C19A C18A 113.9(11) 2_655 . ? C22B C17B F7B 125.1(17) . . ? C22B C17B C18B 124.2(15) . . ? F7B C17B C18B 110.6(14) . . ? F8B C18B C19B 124.4(18) . . ? F8B C18B C17B 127.0(17) . . ? C19B C18B C17B 108.5(15) . . ? C20B C19B C18B 126.8(16) . . ? C20B C19B F9B 116.9(18) . . ? C18B C19B F9B 116.4(17) . . ? C19B C20B F10B 124.6(16) . . ? C19B C20B C21B 122.9(14) . . ? F10B C20B C21B 112.4(14) . . ? F11B C21B C22B 124(2) . . ? F11B C21B C20B 125.7(18) . . ? C22B C21B C20B 110.1(15) . . ? C17B C22B C21B 127.3(17) . . ? C17B C22B F12B 115.5(18) . . ? C21B C22B F12B 117.2(17) . . ? _diffrn_measured_fraction_theta_max 0.899 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.899 _refine_diff_density_max 0.542 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.061 #============================================================================== data_compound5+HBF _database_code_depnum_ccdc_archive 'CCDC 693055' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 N3, C6 F6' _chemical_formula_sum 'C20 H11 F6 N3' _chemical_formula_weight 407.32 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 17.7639(4) _cell_length_b 7.0692(2) _cell_length_c 14.1054(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.9350(16) _cell_angle_gamma 90.00 _cell_volume 1703.24(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10254 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9694 _exptl_absorpt_correction_T_max 0.9929 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19875 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3896 _reflns_number_gt 2901 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0612P)^2^+0.0930P] 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 3896 _refine_ls_number_parameters 270 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1088 _refine_ls_wR_factor_gt 0.0992 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 N1 N 0.42473(6) -0.02830(15) 0.31618(8) 0.0218(3) Uani 1 1 d . . . N2 N 0.51640(7) 0.12406(17) 0.25593(9) 0.0228(3) Uani 1 1 d . . . H2A H 0.5425(9) 0.229(3) 0.2483(11) 0.033(4) Uiso 1 1 d . . . H2B H 0.5104(10) 0.032(3) 0.2111(12) 0.036(5) Uiso 1 1 d . . . N3 N 0.47137(6) 0.28137(15) 0.37319(8) 0.0209(3) Uani 1 1 d . . . C1 C 0.47007(7) 0.12623(17) 0.31652(9) 0.0194(3) Uani 1 1 d . . . C2 C 0.42249(7) 0.28048(18) 0.43030(10) 0.0205(3) Uani 1 1 d . . . H2 H 0.4229 0.3866 0.4718 0.025 Uiso 1 1 calc R . . C3 C 0.37093(7) 0.13307(18) 0.43261(9) 0.0189(3) Uani 1 1 d . . . C4 C 0.37668(8) -0.02056(19) 0.37332(9) 0.0214(3) Uani 1 1 d . . . H4 H 0.3441 -0.1268 0.3738 0.026 Uiso 1 1 calc R . . C5 C 0.31557(7) 0.13902(17) 0.49476(9) 0.0183(3) Uani 1 1 d . . . C6 C 0.34383(8) 0.16272(19) 0.59478(9) 0.0215(3) Uani 1 1 d . . . H6 H 0.3987 0.1756 0.6229 0.026 Uiso 1 1 calc R . . C7 C 0.29401(8) 0.16858(19) 0.65707(10) 0.0237(3) Uani 1 1 d . . . H7 H 0.3155 0.1834 0.7262 0.028 Uiso 1 1 calc R . . C8 C 0.21487(8) 0.15305(19) 0.61839(10) 0.0233(3) Uani 1 1 d . . . H8 H 0.1816 0.1563 0.6608 0.028 Uiso 1 1 calc R . . C9 C 0.18210(8) 0.13205(17) 0.51532(10) 0.0197(3) Uani 1 1 d . . . C10 C 0.09955(8) 0.12123(19) 0.47324(11) 0.0248(3) Uani 1 1 d . . . H10 H 0.0658 0.1271 0.5150 0.030 Uiso 1 1 calc R . . C11 C 0.06825(8) 0.1026(2) 0.37406(11) 0.0280(3) Uani 1 1 d . . . H11 H 0.0131 0.0960 0.3472 0.034 Uiso 1 1 calc R . . C12 C 0.11763(8) 0.0933(2) 0.31121(10) 0.0259(3) Uani 1 1 d . . . H12 H 0.0955 0.0797 0.2421 0.031 Uiso 1 1 calc R . . C13 C 0.19736(8) 0.10354(19) 0.34908(10) 0.0223(3) Uani 1 1 d . . . H13 H 0.2298 0.0976 0.3057 0.027 Uiso 1 1 calc R . . C14 C 0.23228(8) 0.12284(17) 0.45203(9) 0.0179(3) Uani 1 1 d . . . F1 F 0.27674(5) 0.55853(11) 0.36183(6) 0.0311(2) Uani 1 1 d . . . F2 F 0.34479(4) 0.62441(12) 0.55653(6) 0.0324(2) Uani 1 1 d . . . F3 F 0.25342(5) 0.68583(12) 0.68055(6) 0.0343(2) Uani 1 1 d . . . F4 F 0.09540(5) 0.69297(13) 0.60802(6) 0.0388(2) Uani 1 1 d . . . F5 F 0.02770(5) 0.63196(12) 0.41338(7) 0.0382(2) Uani 1 1 d . . . F6 F 0.11872(5) 0.56739(13) 0.28996(6) 0.0350(2) Uani 1 1 d . . . C15 C 0.23210(8) 0.59177(18) 0.42298(10) 0.0227(3) Uani 1 1 d . . . C16 C 0.26652(8) 0.62340(18) 0.52190(10) 0.0231(3) Uani 1 1 d . . . C17 C 0.22063(8) 0.65569(19) 0.58442(10) 0.0245(3) Uani 1 1 d . . . C18 C 0.14023(8) 0.6577(2) 0.54784(10) 0.0261(3) Uani 1 1 d . . . C19 C 0.10573(8) 0.62756(19) 0.44880(11) 0.0263(3) Uani 1 1 d . . . C20 C 0.15170(8) 0.59509(19) 0.38626(10) 0.0242(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 N1 0.0222(6) 0.0195(6) 0.0254(6) 0.0002(5) 0.0093(5) -0.0001(5) N2 0.0246(6) 0.0192(6) 0.0285(6) 0.0003(5) 0.0138(5) -0.0005(5) N3 0.0186(6) 0.0205(6) 0.0247(6) 0.0002(5) 0.0080(5) 0.0001(5) C1 0.0172(6) 0.0194(7) 0.0217(6) 0.0030(5) 0.0054(5) 0.0033(5) C2 0.0202(7) 0.0207(7) 0.0205(6) -0.0011(5) 0.0054(5) 0.0015(5) C3 0.0169(6) 0.0216(7) 0.0178(6) 0.0025(5) 0.0042(5) 0.0016(5) C4 0.0214(7) 0.0197(7) 0.0251(7) 0.0011(5) 0.0096(6) -0.0011(5) C5 0.0204(7) 0.0152(6) 0.0203(6) 0.0025(5) 0.0070(5) 0.0009(5) C6 0.0204(7) 0.0217(7) 0.0216(7) 0.0013(5) 0.0047(6) -0.0010(5) C7 0.0300(8) 0.0248(7) 0.0157(6) -0.0002(5) 0.0051(6) -0.0005(6) C8 0.0272(7) 0.0226(7) 0.0241(7) -0.0001(6) 0.0135(6) -0.0007(6) C9 0.0220(7) 0.0155(6) 0.0231(7) 0.0001(5) 0.0086(6) 0.0006(5) C10 0.0216(7) 0.0233(7) 0.0322(8) -0.0004(6) 0.0120(6) 0.0012(5) C11 0.0185(7) 0.0285(8) 0.0350(8) -0.0007(6) 0.0038(6) 0.0005(6) C12 0.0260(7) 0.0279(7) 0.0213(7) -0.0007(6) 0.0022(6) 0.0016(6) C13 0.0245(7) 0.0222(7) 0.0214(7) 0.0009(6) 0.0081(6) 0.0009(5) C14 0.0203(7) 0.0138(6) 0.0200(6) 0.0019(5) 0.0065(5) 0.0005(5) F1 0.0351(5) 0.0303(5) 0.0326(5) -0.0008(4) 0.0172(4) -0.0006(4) F2 0.0214(4) 0.0320(5) 0.0409(5) -0.0019(4) 0.0036(4) -0.0001(3) F3 0.0415(5) 0.0362(5) 0.0212(4) -0.0016(4) 0.0015(4) 0.0032(4) F4 0.0393(5) 0.0460(6) 0.0371(5) -0.0012(4) 0.0208(4) 0.0051(4) F5 0.0201(4) 0.0445(6) 0.0464(6) -0.0017(4) 0.0033(4) 0.0035(4) F6 0.0393(5) 0.0381(5) 0.0222(4) -0.0008(4) -0.0005(4) 0.0029(4) C15 0.0277(7) 0.0176(6) 0.0254(7) 0.0020(6) 0.0115(6) 0.0013(5) C16 0.0200(7) 0.0177(7) 0.0295(8) 0.0025(6) 0.0035(6) 0.0011(5) C17 0.0315(8) 0.0199(7) 0.0200(7) 0.0015(6) 0.0033(6) 0.0010(6) C18 0.0285(8) 0.0243(7) 0.0289(8) 0.0023(6) 0.0138(6) 0.0043(6) C19 0.0205(7) 0.0235(7) 0.0324(8) 0.0024(6) 0.0029(6) 0.0025(6) C20 0.0289(8) 0.0204(7) 0.0202(7) 0.0016(6) 0.0016(6) 0.0015(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 N1 C4 1.3262(17) . ? N1 C1 1.3565(17) . ? N2 C1 1.3395(17) . ? N2 H2A 0.897(18) . ? N2 H2B 0.893(18) . ? N3 C2 1.3369(17) . ? N3 C1 1.3535(17) . ? C2 C3 1.3936(18) . ? C2 H2 0.9500 . ? C3 C4 1.3915(18) . ? C3 C5 1.4869(18) . ? C4 H4 0.9500 . ? C5 C6 1.3717(18) . ? C5 C14 1.4409(18) . ? C6 C7 1.4084(19) . ? C6 H6 0.9500 . ? C7 C8 1.366(2) . ? C7 H7 0.9500 . ? C8 C9 1.4177(19) . ? C8 H8 0.9500 . ? C9 C10 1.4250(19) . ? C9 C14 1.4258(18) . ? C10 C11 1.362(2) . ? C10 H10 0.9500 . ? C11 C12 1.409(2) . ? C11 H11 0.9500 . ? C12 C13 1.3716(19) . ? C12 H12 0.9500 . ? C13 C14 1.4203(18) . ? C13 H13 0.9500 . ? F1 C15 1.3429(15) . ? F2 C16 1.3414(16) . ? F3 C17 1.3377(15) . ? F4 C18 1.3374(16) . ? F5 C19 1.3386(16) . ? F6 C20 1.3377(15) . ? C15 C16 1.379(2) . ? C15 C20 1.3793(19) . ? C16 C17 1.374(2) . ? C17 C18 1.379(2) . ? C18 C19 1.379(2) . ? C19 C20 1.376(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 C1 116.43(11) . . ? C1 N2 H2A 119.7(10) . . ? C1 N2 H2B 119.0(11) . . ? H2A N2 H2B 118.9(15) . . ? C2 N3 C1 116.32(11) . . ? N2 C1 N3 118.18(12) . . ? N2 C1 N1 117.17(12) . . ? N3 C1 N1 124.65(12) . . ? N3 C2 C3 123.87(12) . . ? N3 C2 H2 118.1 . . ? C3 C2 H2 118.1 . . ? C4 C3 C2 114.36(12) . . ? C4 C3 C5 123.10(11) . . ? C2 C3 C5 122.54(12) . . ? N1 C4 C3 124.28(12) . . ? N1 C4 H4 117.9 . . ? C3 C4 H4 117.9 . . ? C6 C5 C14 118.93(12) . . ? C6 C5 C3 119.70(11) . . ? C14 C5 C3 121.37(11) . . ? C5 C6 C7 122.01(12) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C8 C7 C6 120.17(12) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 120.40(12) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C10 121.25(12) . . ? C8 C9 C14 119.70(12) . . ? C10 C9 C14 119.05(12) . . ? C11 C10 C9 121.07(13) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 120.09(13) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 120.46(12) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 121.18(13) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C13 C14 C9 118.16(12) . . ? C13 C14 C5 123.05(12) . . ? C9 C14 C5 118.77(11) . . ? F1 C15 C16 120.15(12) . . ? F1 C15 C20 119.67(12) . . ? C16 C15 C20 120.18(13) . . ? F2 C16 C17 120.24(12) . . ? F2 C16 C15 119.77(12) . . ? C17 C16 C15 119.99(12) . . ? F3 C17 C16 120.46(12) . . ? F3 C17 C18 119.72(13) . . ? C16 C17 C18 119.82(12) . . ? F4 C18 C17 120.03(12) . . ? F4 C18 C19 119.69(13) . . ? C17 C18 C19 120.27(13) . . ? F5 C19 C20 120.04(12) . . ? F5 C19 C18 120.07(13) . . ? C20 C19 C18 119.89(13) . . ? F6 C20 C19 120.26(12) . . ? F6 C20 C15 119.90(13) . . ? C19 C20 C15 119.85(12) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.244 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.051 #============================================================================== data_compound6+HBF _database_code_depnum_ccdc_archive 'CCDC 693056' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C14 H11 N3, 0.5(C6 F6)' _chemical_formula_sum 'C17 H11 F3 N3' _chemical_formula_weight 314.29 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 14.7028(6) _cell_length_b 7.3888(4) _cell_length_c 13.7709(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.236(3) _cell_angle_gamma 90.00 _cell_volume 1403.68(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 26353 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9653 _exptl_absorpt_correction_T_max 0.9653 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17838 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3204 _reflns_number_gt 2483 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0772P)^2^+0.2583P] 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 3204 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 N1 N 0.42357(8) 0.48055(14) 0.32747(9) 0.0249(3) Uani 1 1 d . . . N2 N 0.50085(9) 0.31640(16) 0.23718(9) 0.0252(3) Uani 1 1 d . . . H2A H 0.5226(12) 0.214(3) 0.2238(13) 0.034(4) Uiso 1 1 d . . . H2B H 0.5071(12) 0.415(3) 0.2069(13) 0.036(4) Uiso 1 1 d . . . N3 N 0.45648(8) 0.16453(14) 0.36047(9) 0.0245(3) Uani 1 1 d . . . C1 C 0.45914(9) 0.31977(16) 0.30922(10) 0.0221(3) Uani 1 1 d . . . C2 C 0.41070(9) 0.17141(17) 0.42868(10) 0.0249(3) Uani 1 1 d . . . H2 H 0.4071 0.0634 0.4646 0.030 Uiso 1 1 calc R . . C3 C 0.36765(9) 0.32709(17) 0.45066(10) 0.0232(3) Uani 1 1 d . . . C4 C 0.37923(9) 0.47977(18) 0.39676(10) 0.0255(3) Uani 1 1 d . . . H4 H 0.3537 0.5911 0.4105 0.031 Uiso 1 1 calc R . . C5 C 0.31535(9) 0.33062(18) 0.52540(10) 0.0236(3) Uani 1 1 d . . . C6 C 0.26923(10) 0.17176(18) 0.54436(10) 0.0265(3) Uani 1 1 d . . . H6 H 0.2723 0.0632 0.5086 0.032 Uiso 1 1 calc R . . C7 C 0.22071(10) 0.17250(19) 0.61295(10) 0.0281(3) Uani 1 1 d . . . H7 H 0.1907 0.0645 0.6241 0.034 Uiso 1 1 calc R . . C8 C 0.21446(9) 0.33088(19) 0.66756(10) 0.0269(3) Uani 1 1 d . . . C9 C 0.16325(10) 0.3373(2) 0.73832(11) 0.0321(3) Uani 1 1 d . . . H9 H 0.1326 0.2311 0.7508 0.039 Uiso 1 1 calc R . . C10 C 0.15763(11) 0.4939(2) 0.78841(11) 0.0354(4) Uani 1 1 d . . . H10 H 0.1226 0.4965 0.8348 0.042 Uiso 1 1 calc R . . C11 C 0.20372(10) 0.6519(2) 0.77139(11) 0.0351(4) Uani 1 1 d . . . H11 H 0.1998 0.7602 0.8069 0.042 Uiso 1 1 calc R . . C12 C 0.25423(10) 0.6511(2) 0.70427(11) 0.0306(3) Uani 1 1 d . . . H12 H 0.2856 0.7583 0.6942 0.037 Uiso 1 1 calc R . . C13 C 0.25991(9) 0.49081(18) 0.64970(10) 0.0258(3) Uani 1 1 d . . . C14 C 0.30990(9) 0.48615(18) 0.57805(10) 0.0250(3) Uani 1 1 d . . . H14 H 0.3404 0.5931 0.5662 0.030 Uiso 1 1 calc R . . F1 F 0.00018(7) 0.20301(13) 0.38384(7) 0.0450(3) Uani 1 1 d . . . F2 F 0.09063(7) 0.51047(14) 0.35822(7) 0.0480(3) Uani 1 1 d . . . F3 F 0.09154(7) 0.80550(13) 0.47525(8) 0.0492(3) Uani 1 1 d . . . C15 C 0.00013(11) 0.3494(2) 0.44130(11) 0.0344(4) Uani 1 1 d . . . C16 C 0.04655(11) 0.5044(2) 0.42870(11) 0.0346(3) Uani 1 1 d . . . C17 C 0.04646(11) 0.6547(2) 0.48781(12) 0.0354(4) 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 N1 0.0290(6) 0.0178(5) 0.0282(6) 0.0001(4) 0.0102(5) 0.0008(4) N2 0.0319(6) 0.0151(5) 0.0305(6) -0.0010(4) 0.0132(5) -0.0005(5) N3 0.0267(5) 0.0179(5) 0.0288(6) 0.0006(4) 0.0095(5) 0.0011(4) C1 0.0219(6) 0.0181(6) 0.0241(6) -0.0016(5) 0.0052(5) -0.0018(5) C2 0.0271(6) 0.0200(6) 0.0268(6) 0.0023(5) 0.0080(5) 0.0001(5) C3 0.0224(6) 0.0214(6) 0.0239(6) -0.0014(5) 0.0057(5) -0.0005(5) C4 0.0274(6) 0.0199(6) 0.0280(7) -0.0014(5) 0.0081(5) 0.0028(5) C5 0.0226(6) 0.0238(7) 0.0218(6) 0.0013(5) 0.0042(5) 0.0022(5) C6 0.0288(6) 0.0227(7) 0.0259(7) 0.0007(5) 0.0067(5) 0.0008(5) C7 0.0290(7) 0.0246(7) 0.0283(7) 0.0040(5) 0.0068(5) -0.0010(5) C8 0.0242(6) 0.0301(7) 0.0233(6) 0.0029(5) 0.0044(5) 0.0015(5) C9 0.0291(7) 0.0382(8) 0.0271(7) 0.0042(6) 0.0073(6) 0.0004(6) C10 0.0294(7) 0.0495(9) 0.0271(7) -0.0020(6) 0.0095(6) 0.0036(7) C11 0.0285(7) 0.0404(8) 0.0329(8) -0.0101(6) 0.0062(6) 0.0040(6) C12 0.0260(6) 0.0304(7) 0.0321(7) -0.0056(6) 0.0059(6) 0.0013(6) C13 0.0228(6) 0.0261(7) 0.0240(6) -0.0014(5) 0.0024(5) 0.0017(5) C14 0.0232(6) 0.0234(6) 0.0261(6) 0.0002(5) 0.0055(5) 0.0001(5) F1 0.0461(5) 0.0333(5) 0.0479(6) -0.0116(4) 0.0064(4) 0.0057(4) F2 0.0472(6) 0.0541(6) 0.0446(6) -0.0053(5) 0.0183(4) -0.0054(5) F3 0.0567(6) 0.0339(5) 0.0518(6) 0.0021(4) 0.0121(5) -0.0127(4) C15 0.0334(7) 0.0282(8) 0.0328(7) -0.0033(6) 0.0002(6) 0.0055(6) C16 0.0314(7) 0.0373(8) 0.0309(7) 0.0006(6) 0.0053(6) 0.0027(6) C17 0.0340(7) 0.0283(8) 0.0360(8) 0.0029(6) 0.0019(6) -0.0022(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 N1 C4 1.3288(18) . ? N1 C1 1.3561(16) . ? N2 C1 1.3348(18) . ? N2 H2A 0.869(19) . ? N2 H2B 0.86(2) . ? N3 C2 1.3325(18) . ? N3 C1 1.3544(16) . ? C2 C3 1.3957(18) . ? C2 H2 0.9500 . ? C3 C4 1.3928(18) . ? C3 C5 1.4829(19) . ? C4 H4 0.9500 . ? C5 C14 1.3758(18) . ? C5 C6 1.4242(19) . ? C6 C7 1.366(2) . ? C6 H6 0.9500 . ? C7 C8 1.411(2) . ? C7 H7 0.9500 . ? C8 C13 1.4202(19) . ? C8 C9 1.423(2) . ? C9 C10 1.364(2) . ? C9 H9 0.9500 . ? C10 C11 1.409(2) . ? C10 H10 0.9500 . ? C11 C12 1.371(2) . ? C11 H11 0.9500 . ? C12 C13 1.4207(19) . ? C12 H12 0.9500 . ? C13 C14 1.420(2) . ? C14 H14 0.9500 . ? F1 C15 1.3402(17) . ? F2 C16 1.3413(18) . ? F3 C17 1.3380(18) . ? C15 C17 1.373(2) 3_566 ? C15 C16 1.375(2) . ? C16 C17 1.377(2) . ? C17 C15 1.373(2) 3_566 ? 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 C4 N1 C1 116.47(11) . . ? C1 N2 H2A 118.1(11) . . ? C1 N2 H2B 119.8(12) . . ? H2A N2 H2B 122.0(16) . . ? C2 N3 C1 116.59(11) . . ? N2 C1 N3 118.36(11) . . ? N2 C1 N1 117.38(11) . . ? N3 C1 N1 124.26(12) . . ? N3 C2 C3 124.19(12) . . ? N3 C2 H2 117.9 . . ? C3 C2 H2 117.9 . . ? C4 C3 C2 113.82(12) . . ? C4 C3 C5 122.95(11) . . ? C2 C3 C5 123.23(11) . . ? N1 C4 C3 124.54(12) . . ? N1 C4 H4 117.7 . . ? C3 C4 H4 117.7 . . ? C14 C5 C6 118.27(12) . . ? C14 C5 C3 121.28(12) . . ? C6 C5 C3 120.45(11) . . ? C7 C6 C5 121.26(12) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C8 121.17(13) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C7 C8 C13 118.45(13) . . ? C7 C8 C9 122.66(13) . . ? C13 C8 C9 118.88(13) . . ? C10 C9 C8 120.86(14) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 120.12(14) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 120.82(14) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 120.29(14) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C8 119.19(12) . . ? C14 C13 C12 121.80(13) . . ? C8 C13 C12 119.01(13) . . ? C5 C14 C13 121.66(12) . . ? C5 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? F1 C15 C17 120.29(14) . 3_566 ? F1 C15 C16 119.75(15) . . ? C17 C15 C16 119.96(14) 3_566 . ? F2 C16 C15 120.28(14) . . ? F2 C16 C17 120.03(15) . . ? C15 C16 C17 119.69(15) . . ? F3 C17 C15 120.08(14) . 3_566 ? F3 C17 C16 119.56(15) . . ? C15 C17 C16 120.36(14) 3_566 . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.331 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.050 #============================================================================== data_compound4+AgBF4 _database_code_depnum_ccdc_archive 'CCDC 693057' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C10 H9 N3)2 Ag, B F4, O1.43' _chemical_formula_sum 'C20 H18 Ag B F4 N6 O1.43' _chemical_formula_weight 560.04 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 'C 2/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 7.49100(10) _cell_length_b 19.1270(4) _cell_length_c 15.8200(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.8670(15) _cell_angle_gamma 90.00 _cell_volume 2263.86(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10787 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1118 _exptl_absorpt_coefficient_mu 0.950 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7636 _exptl_absorpt_correction_T_max 0.9279 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19690 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2606 _reflns_number_gt 2239 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Disorder of BF4 on a two-fold axes. Two disordered waterpositions with a occupation of 0.36 and 0.35 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^)+(0.0397P)^2^+7.1068P] 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 2606 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0857 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 1.0000 0.0000 0.0000 0.02500(10) Uani 1 2 d S . . N1 N 0.8678(3) 0.07958(10) 0.07337(12) 0.0214(4) Uani 1 1 d . . . N2 N 0.8540(3) 0.15931(12) -0.03789(14) 0.0337(5) Uani 1 1 d . . . H2A H 0.8269 0.2010 -0.0582 0.040 Uiso 1 1 calc R . . H2B H 0.8998 0.1276 -0.0708 0.040 Uiso 1 1 calc R . . N3 N 0.7553(3) 0.19563(11) 0.08885(13) 0.0258(4) Uani 1 1 d . . . C1 C 0.8258(3) 0.14420(13) 0.04257(15) 0.0234(5) Uani 1 1 d . . . C2 C 0.7257(3) 0.18132(13) 0.16866(16) 0.0255(5) Uani 1 1 d . . . H2 H 0.6742 0.2169 0.2016 0.031 Uiso 1 1 calc R . . C3 C 0.7653(3) 0.11725(13) 0.20766(15) 0.0216(5) Uani 1 1 d . . . C4 C 0.8368(3) 0.06751(12) 0.15515(15) 0.0213(5) Uani 1 1 d . . . H4 H 0.8652 0.0227 0.1781 0.026 Uiso 1 1 calc R . . C5 C 0.7299(3) 0.10457(13) 0.29748(15) 0.0234(5) Uani 1 1 d . . . C6 C 0.7404(4) 0.15976(14) 0.35578(16) 0.0291(5) Uani 1 1 d . . . H6 H 0.7729 0.2051 0.3376 0.035 Uiso 1 1 calc R . . C7 C 0.7037(4) 0.14867(16) 0.44002(17) 0.0346(6) Uani 1 1 d . . . H7 H 0.7090 0.1867 0.4787 0.042 Uiso 1 1 calc R . . C8 C 0.6597(4) 0.08278(17) 0.46790(18) 0.0363(7) Uani 1 1 d . . . H8 H 0.6364 0.0752 0.5257 0.044 Uiso 1 1 calc R . . C9 C 0.6498(4) 0.02774(17) 0.41072(18) 0.0330(6) Uani 1 1 d . . . H9 H 0.6196 -0.0177 0.4296 0.040 Uiso 1 1 calc R . . C10 C 0.6837(3) 0.03843(14) 0.32590(16) 0.0269(5) Uani 1 1 d . . . H10 H 0.6753 0.0004 0.2873 0.032 Uiso 1 1 calc R . . F1 F 1.0066(4) -0.08637(10) 0.32059(15) 0.0829(10) Uani 1 1 d . . 1 F2 F 1.2329(8) -0.1455(5) 0.2528(4) 0.113(3) Uani 0.50 1 d P A 1 F3 F 1.0000 -0.18564(18) 0.2500 0.114(2) Uani 1 2 d S . 1 B1 B 1.0607(10) -0.1256(3) 0.2589(5) 0.0394(17) Uani 0.50 1 d P . 1 O1 O 1.4024(15) -0.1156(6) 0.3194(7) 0.087(5) Uiso 0.363(13) 1 d P B 2 O2 O 1.5031(18) -0.1528(7) 0.2960(8) 0.101(6) Uiso 0.346(13) 1 d P . 3 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 0.03494(17) 0.02003(15) 0.02031(15) -0.00065(9) 0.00409(10) 0.00828(10) N1 0.0263(10) 0.0195(10) 0.0184(9) -0.0005(8) 0.0012(8) 0.0048(8) N2 0.0563(15) 0.0277(11) 0.0178(10) 0.0040(9) 0.0079(10) 0.0188(11) N3 0.0367(12) 0.0217(10) 0.0194(10) 0.0030(8) 0.0053(8) 0.0099(9) C1 0.0285(12) 0.0230(12) 0.0189(11) 0.0018(9) 0.0022(9) 0.0062(9) C2 0.0325(13) 0.0238(12) 0.0208(12) 0.0015(9) 0.0056(10) 0.0081(10) C3 0.0243(11) 0.0222(11) 0.0184(11) 0.0024(9) 0.0016(9) 0.0020(9) C4 0.0249(12) 0.0193(11) 0.0197(11) 0.0018(9) 0.0002(9) 0.0017(9) C5 0.0236(11) 0.0268(12) 0.0201(11) 0.0041(10) 0.0036(9) 0.0032(9) C6 0.0381(14) 0.0279(13) 0.0217(12) 0.0021(10) 0.0070(10) 0.0059(11) C7 0.0408(16) 0.0411(16) 0.0228(13) -0.0015(11) 0.0085(11) 0.0084(13) C8 0.0328(14) 0.0539(18) 0.0227(13) 0.0104(12) 0.0076(11) 0.0021(13) C9 0.0286(13) 0.0406(16) 0.0296(14) 0.0147(12) 0.0007(11) -0.0051(12) C10 0.0255(12) 0.0300(13) 0.0249(12) 0.0051(10) -0.0012(9) -0.0015(10) F1 0.162(3) 0.0286(10) 0.0642(14) -0.0132(10) 0.0683(17) -0.0254(13) F2 0.076(4) 0.175(7) 0.090(4) 0.043(5) 0.020(3) 0.032(4) F3 0.233(6) 0.0287(17) 0.076(3) 0.000 -0.030(3) 0.000 B1 0.059(5) 0.028(3) 0.033(4) 0.008(3) 0.016(4) -0.004(3) _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 2.182(2) . ? Ag1 N1 2.182(2) 5_755 ? N1 C4 1.346(3) . ? N1 C1 1.360(3) . ? N2 C1 1.332(3) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 C2 1.321(3) . ? N3 C1 1.350(3) . ? C2 C3 1.397(3) . ? C2 H2 0.9500 . ? C3 C4 1.388(3) . ? C3 C5 1.478(3) . ? C4 H4 0.9500 . ? C5 C10 1.392(4) . ? C5 C6 1.401(4) . ? C6 C7 1.390(4) . ? C6 H6 0.9500 . ? C7 C8 1.381(4) . ? C7 H7 0.9500 . ? C8 C9 1.388(5) . ? C8 H8 0.9500 . ? C9 C10 1.393(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? F1 B1 1.311(8) . ? F1 B1 1.529(8) 2_755 ? F2 B1 1.353(9) . ? F3 B1 1.241(7) . ? F3 B1 1.241(7) 2_755 ? B1 B1 0.939(15) 2_755 ? B1 F1 1.528(8) 2_755 ? O2 O2 1.45(2) 2_855 ? 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 180.0 . 5_755 ? C4 N1 C1 116.9(2) . . ? C4 N1 Ag1 119.77(16) . . ? C1 N1 Ag1 123.14(16) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C2 N3 C1 117.1(2) . . ? N2 C1 N3 116.4(2) . . ? N2 C1 N1 119.6(2) . . ? N3 C1 N1 123.9(2) . . ? N3 C2 C3 124.2(2) . . ? N3 C2 H2 117.9 . . ? C3 C2 H2 117.9 . . ? C4 C3 C2 114.6(2) . . ? C4 C3 C5 123.8(2) . . ? C2 C3 C5 121.6(2) . . ? N1 C4 C3 123.2(2) . . ? N1 C4 H4 118.4 . . ? C3 C4 H4 118.4 . . ? C10 C5 C6 118.6(2) . . ? C10 C5 C3 121.3(2) . . ? C6 C5 C3 120.1(2) . . ? C7 C6 C5 120.6(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C8 C7 C6 120.5(3) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 119.3(3) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C10 120.7(3) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C5 C10 C9 120.3(3) . . ? C5 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? B1 F1 B1 37.6(6) . 2_755 ? B1 F3 B1 44.5(7) . 2_755 ? B1 B1 F3 67.8(4) 2_755 . ? B1 B1 F1 83.9(7) 2_755 . ? F3 B1 F1 119.3(5) . . ? B1 B1 F2 153.0(10) 2_755 . ? F3 B1 F2 94.4(6) . . ? F1 B1 F2 123.1(7) . . ? B1 B1 F1 58.5(7) 2_755 2_755 ? F3 B1 F1 104.9(5) . 2_755 ? F1 B1 F1 103.3(5) . 2_755 ? F2 B1 F1 110.9(5) . 2_755 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.872 _refine_diff_density_min -0.795 _refine_diff_density_rms 0.089 #============================================================================== data_compound5+AgBF4 _database_code_depnum_ccdc_archive 'CCDC 693058' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C14 H11 N3)2 Ag, B F4' _chemical_formula_sum 'C28 H22 Ag B F4 N6' _chemical_formula_weight 637.20 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 18.8540(5) _cell_length_b 13.3354(3) _cell_length_c 10.1094(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.6513(15) _cell_angle_gamma 90.00 _cell_volume 2519.13(12) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 32870 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.862 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8265 _exptl_absorpt_correction_T_max 0.9830 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41367 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5751 _reflns_number_gt 4191 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0272P)^2^+2.6406P] 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 5751 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0831 _refine_ls_wR_factor_gt 0.0749 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.476590(12) 0.371674(19) 0.01612(2) 0.03601(8) Uani 1 1 d . . . N1 N 0.54378(11) 0.36731(18) 0.2080(2) 0.0264(5) Uani 1 1 d . . . N2 N 0.44421(12) 0.36513(18) 0.3214(2) 0.0312(5) Uani 1 1 d . . . H2A H 0.4251 0.3573 0.3956 0.037 Uiso 1 1 calc R . . H2B H 0.4167 0.3791 0.2463 0.037 Uiso 1 1 calc R . . N3 N 0.55334(13) 0.3345(2) 0.4418(2) 0.0336(6) Uani 1 1 d . . . N4 N 0.40470(12) 0.36742(18) -0.1697(2) 0.0275(5) Uani 1 1 d . . . N5 N 0.49763(12) 0.37364(19) -0.2981(2) 0.0341(6) Uani 1 1 d . . . H5A H 0.5139 0.3671 -0.3752 0.041 Uiso 1 1 calc R . . H5B H 0.5271 0.3895 -0.2261 0.041 Uiso 1 1 calc R . . N6 N 0.38625(12) 0.33521(19) -0.4049(2) 0.0312(5) Uani 1 1 d . . . C1 C 0.51494(14) 0.3559(2) 0.3229(3) 0.0262(6) Uani 1 1 d . . . C2 C 0.62390(15) 0.3278(2) 0.4452(3) 0.0348(7) Uani 1 1 d . . . H2 H 0.6515 0.3121 0.5282 0.042 Uiso 1 1 calc R . . C3 C 0.65984(15) 0.3420(2) 0.3357(3) 0.0286(6) Uani 1 1 d . . . C4 C 0.61579(14) 0.3615(2) 0.2173(3) 0.0282(6) Uani 1 1 d . . . H4 H 0.6374 0.3712 0.1386 0.034 Uiso 1 1 calc R . . C5 C 0.73915(14) 0.3319(2) 0.3440(3) 0.0295(6) Uani 1 1 d . . . C6 C 0.78619(15) 0.3932(2) 0.4324(3) 0.0302(6) Uani 1 1 d . . . C7 C 0.76224(17) 0.4681(2) 0.5151(3) 0.0366(7) Uani 1 1 d . . . H7 H 0.7123 0.4779 0.5147 0.044 Uiso 1 1 calc R . . C8 C 0.80933(18) 0.5269(3) 0.5956(3) 0.0462(8) Uani 1 1 d . . . H8 H 0.7919 0.5762 0.6511 0.055 Uiso 1 1 calc R . . C9 C 0.88362(19) 0.5145(3) 0.5964(4) 0.0492(9) Uani 1 1 d . . . H9 H 0.9162 0.5567 0.6504 0.059 Uiso 1 1 calc R . . C10 C 0.90878(17) 0.4423(3) 0.5199(3) 0.0433(8) Uani 1 1 d . . . H10 H 0.9590 0.4340 0.5221 0.052 Uiso 1 1 calc R . . C11 C 0.86157(15) 0.3795(2) 0.4372(3) 0.0338(6) Uani 1 1 d . . . C12 C 0.88782(16) 0.3035(3) 0.3587(3) 0.0422(8) Uani 1 1 d . . . H12 H 0.9379 0.2927 0.3639 0.051 Uiso 1 1 calc R . . C13 C 0.84182(17) 0.2461(3) 0.2760(3) 0.0442(8) Uani 1 1 d . . . H13 H 0.8599 0.1954 0.2236 0.053 Uiso 1 1 calc R . . C14 C 0.76749(16) 0.2613(2) 0.2674(3) 0.0371(7) Uani 1 1 d . . . H14 H 0.7362 0.2216 0.2072 0.045 Uiso 1 1 calc R . . C15 C 0.42854(14) 0.3596(2) -0.2902(3) 0.0273(6) Uani 1 1 d . . . C16 C 0.31765(15) 0.3222(2) -0.3973(3) 0.0334(7) Uani 1 1 d . . . H16 H 0.2875 0.3051 -0.4770 0.040 Uiso 1 1 calc R . . C17 C 0.28598(15) 0.3318(2) -0.2810(3) 0.0311(6) Uani 1 1 d . . . C18 C 0.33348(15) 0.3544(2) -0.1681(3) 0.0304(6) Uani 1 1 d . . . H18 H 0.3152 0.3611 -0.0854 0.037 Uiso 1 1 calc R . . C19 C 0.20750(16) 0.3135(2) -0.2858(3) 0.0344(7) Uani 1 1 d . . . C20 C 0.17793(17) 0.2308(2) -0.3549(3) 0.0384(7) Uani 1 1 d . . . H20 H 0.2089 0.1860 -0.3927 0.046 Uiso 1 1 calc R . . C21 C 0.10462(18) 0.2100(3) -0.3718(3) 0.0487(9) Uani 1 1 d . . . H21 H 0.0862 0.1530 -0.4212 0.058 Uiso 1 1 calc R . . C22 C 0.05921(18) 0.2742(3) -0.3150(3) 0.0488(9) Uani 1 1 d . . . H22 H 0.0093 0.2607 -0.3251 0.059 Uiso 1 1 calc R . . C23 C 0.08651(15) 0.3595(3) -0.2425(3) 0.0373(7) Uani 1 1 d . . . C24 C 0.04116(17) 0.4263(3) -0.1845(3) 0.0483(9) Uani 1 1 d . . . H24 H -0.0087 0.4128 -0.1940 0.058 Uiso 1 1 calc R . . C25 C 0.06656(18) 0.5085(3) -0.1162(4) 0.0516(9) Uani 1 1 d . . . H25 H 0.0347 0.5522 -0.0789 0.062 Uiso 1 1 calc R . . C26 C 0.14011(18) 0.5292(3) -0.1003(3) 0.0465(8) Uani 1 1 d . . . H26 H 0.1578 0.5866 -0.0511 0.056 Uiso 1 1 calc R . . C27 C 0.18675(16) 0.4680(2) -0.1546(3) 0.0356(7) Uani 1 1 d . . . H27 H 0.2362 0.4844 -0.1445 0.043 Uiso 1 1 calc R . . C28 C 0.16184(15) 0.3798(2) -0.2263(3) 0.0351(7) Uani 1 1 d . . . B1 B 0.66122(19) 0.4606(3) -0.1318(4) 0.0377(8) Uani 1 1 d . . . F1 F 0.59632(10) 0.45573(15) -0.08076(17) 0.0468(5) Uani 1 1 d . . . F2 F 0.71008(11) 0.40472(16) -0.0507(2) 0.0587(6) Uani 1 1 d . . . F3 F 0.65077(10) 0.42429(17) -0.26114(18) 0.0519(5) Uani 1 1 d . . . F4 F 0.68018(11) 0.56125(16) -0.1322(2) 0.0566(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 Ag1 0.03426(13) 0.05150(15) 0.02129(11) 0.00086(11) 0.00003(8) 0.00205(12) N1 0.0247(11) 0.0327(13) 0.0218(11) 0.0016(10) 0.0027(9) 0.0000(10) N2 0.0255(11) 0.0453(15) 0.0226(11) 0.0032(11) 0.0023(9) 0.0001(11) N3 0.0292(12) 0.0494(15) 0.0220(12) 0.0038(11) 0.0021(10) 0.0006(12) N4 0.0287(12) 0.0332(13) 0.0208(11) 0.0000(10) 0.0037(9) 0.0022(11) N5 0.0280(12) 0.0513(16) 0.0238(11) -0.0053(12) 0.0060(10) -0.0040(12) N6 0.0308(13) 0.0409(14) 0.0214(12) -0.0004(10) 0.0022(10) 0.0014(11) C1 0.0270(14) 0.0282(16) 0.0232(13) 0.0002(11) 0.0023(11) -0.0022(12) C2 0.0301(15) 0.0505(19) 0.0226(14) 0.0058(13) -0.0010(12) -0.0006(14) C3 0.0284(14) 0.0326(16) 0.0248(14) -0.0016(11) 0.0034(11) -0.0033(12) C4 0.0285(14) 0.0314(16) 0.0255(13) -0.0013(12) 0.0067(11) -0.0029(12) C5 0.0245(14) 0.0372(16) 0.0268(14) 0.0024(12) 0.0036(11) -0.0013(12) C6 0.0284(14) 0.0363(17) 0.0257(14) 0.0067(12) 0.0025(11) -0.0012(12) C7 0.0353(16) 0.0398(18) 0.0336(16) -0.0001(13) -0.0001(13) 0.0017(14) C8 0.051(2) 0.0403(19) 0.0437(19) -0.0086(15) -0.0050(16) 0.0045(16) C9 0.048(2) 0.044(2) 0.050(2) -0.0036(16) -0.0113(16) -0.0100(17) C10 0.0307(16) 0.052(2) 0.0449(19) 0.0055(16) -0.0020(14) -0.0094(15) C11 0.0295(14) 0.0417(17) 0.0298(14) 0.0046(13) 0.0028(12) -0.0040(14) C12 0.0288(16) 0.059(2) 0.0406(18) 0.0005(16) 0.0092(14) 0.0027(15) C13 0.0389(18) 0.053(2) 0.0425(18) -0.0121(16) 0.0105(15) 0.0051(16) C14 0.0319(16) 0.0449(19) 0.0340(16) -0.0061(14) 0.0027(13) -0.0014(14) C15 0.0283(14) 0.0295(16) 0.0238(13) 0.0008(11) 0.0026(11) 0.0033(12) C16 0.0296(15) 0.0416(18) 0.0279(15) -0.0006(13) -0.0006(12) 0.0005(14) C17 0.0265(14) 0.0341(16) 0.0327(15) 0.0043(12) 0.0038(12) 0.0028(13) C18 0.0296(14) 0.0363(17) 0.0268(14) 0.0039(12) 0.0090(11) 0.0051(12) C19 0.0327(16) 0.0423(19) 0.0281(15) 0.0045(13) 0.0034(12) 0.0003(14) C20 0.0374(17) 0.0440(19) 0.0333(16) -0.0017(14) 0.0030(13) -0.0036(15) C21 0.0429(19) 0.055(2) 0.046(2) -0.0016(17) -0.0012(16) -0.0147(17) C22 0.0334(17) 0.070(3) 0.0413(19) 0.0097(17) -0.0003(15) -0.0134(18) C23 0.0259(14) 0.054(2) 0.0314(15) 0.0093(15) 0.0016(12) -0.0029(14) C24 0.0313(17) 0.070(3) 0.0437(19) 0.0095(18) 0.0048(15) 0.0043(17) C25 0.0383(18) 0.071(3) 0.048(2) 0.0031(19) 0.0130(16) 0.0173(19) C26 0.0445(19) 0.054(2) 0.0413(18) 0.0016(16) 0.0076(15) 0.0079(17) C27 0.0323(15) 0.0411(18) 0.0338(16) -0.0003(13) 0.0060(13) 0.0029(14) C28 0.0280(14) 0.0491(19) 0.0279(14) 0.0102(14) 0.0026(11) 0.0033(14) B1 0.0362(19) 0.042(2) 0.0328(18) -0.0025(15) -0.0024(15) 0.0000(16) F1 0.0468(11) 0.0632(13) 0.0308(9) -0.0063(9) 0.0062(8) -0.0043(10) F2 0.0536(12) 0.0634(14) 0.0541(12) -0.0047(10) -0.0108(10) 0.0155(11) F3 0.0452(11) 0.0742(14) 0.0366(10) -0.0141(10) 0.0065(8) 0.0057(10) F4 0.0586(13) 0.0527(13) 0.0560(13) 0.0027(10) -0.0018(10) -0.0142(10) _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 N4 2.166(2) . ? Ag1 N1 2.172(2) . ? N1 C4 1.351(3) . ? N1 C1 1.354(3) . ? N2 C1 1.337(3) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 C2 1.329(4) . ? N3 C1 1.349(3) . ? N4 C18 1.356(3) . ? N4 C15 1.357(3) . ? N5 C15 1.329(3) . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? N6 C16 1.317(4) . ? N6 C15 1.356(3) . ? C2 C3 1.386(4) . ? C2 H2 0.9500 . ? C3 C4 1.387(4) . ? C3 C5 1.493(4) . ? C4 H4 0.9500 . ? C5 C14 1.372(4) . ? C5 C6 1.429(4) . ? C6 C7 1.415(4) . ? C6 C11 1.427(4) . ? C7 C8 1.369(4) . ? C7 H7 0.9500 . ? C8 C9 1.409(5) . ? C8 H8 0.9500 . ? C9 C10 1.359(5) . ? C9 H9 0.9500 . ? C10 C11 1.413(4) . ? C10 H10 0.9500 . ? C11 C12 1.416(4) . ? C12 C13 1.358(5) . ? C12 H12 0.9500 . ? C13 C14 1.407(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C16 C17 1.394(4) . ? C16 H16 0.9500 . ? C17 C18 1.387(4) . ? C17 C19 1.494(4) . ? C18 H18 0.9500 . ? C19 C20 1.382(4) . ? C19 C28 1.421(4) . ? C20 C21 1.398(4) . ? C20 H20 0.9500 . ? C21 C22 1.388(5) . ? C21 H21 0.9500 . ? C22 C23 1.413(5) . ? C22 H22 0.9500 . ? C23 C24 1.414(5) . ? C23 C28 1.433(4) . ? C24 C25 1.350(5) . ? C24 H24 0.9500 . ? C25 C26 1.402(5) . ? C25 H25 0.9500 . ? C26 C27 1.367(4) . ? C26 H26 0.9500 . ? C27 C28 1.429(4) . ? C27 H27 0.9500 . ? B1 F2 1.369(4) . ? B1 F3 1.384(4) . ? B1 F4 1.389(4) . ? B1 F1 1.391(4) . ? 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 N4 Ag1 N1 175.72(8) . . ? C4 N1 C1 116.7(2) . . ? C4 N1 Ag1 121.65(17) . . ? C1 N1 Ag1 121.05(17) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C2 N3 C1 117.0(2) . . ? C18 N4 C15 116.6(2) . . ? C18 N4 Ag1 119.92(17) . . ? C15 N4 Ag1 122.45(18) . . ? C15 N5 H5A 120.0 . . ? C15 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C16 N6 C15 116.9(2) . . ? N2 C1 N3 116.4(2) . . ? N2 C1 N1 119.6(2) . . ? N3 C1 N1 124.0(2) . . ? N3 C2 C3 124.4(3) . . ? N3 C2 H2 117.8 . . ? C3 C2 H2 117.8 . . ? C2 C3 C4 114.5(3) . . ? C2 C3 C5 122.3(3) . . ? C4 C3 C5 123.1(2) . . ? N1 C4 C3 123.5(2) . . ? N1 C4 H4 118.3 . . ? C3 C4 H4 118.3 . . ? C14 C5 C6 119.3(3) . . ? C14 C5 C3 119.5(3) . . ? C6 C5 C3 121.1(3) . . ? C7 C6 C11 117.7(3) . . ? C7 C6 C5 123.6(3) . . ? C11 C6 C5 118.7(3) . . ? C8 C7 C6 121.5(3) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C7 C8 C9 120.1(3) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.1(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 121.1(3) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C10 C11 C12 121.1(3) . . ? C10 C11 C6 119.3(3) . . ? C12 C11 C6 119.6(3) . . ? C13 C12 C11 120.4(3) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.4(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C5 C14 C13 121.6(3) . . ? C5 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? N5 C15 N6 116.9(2) . . ? N5 C15 N4 119.2(2) . . ? N6 C15 N4 123.9(2) . . ? N6 C16 C17 124.8(3) . . ? N6 C16 H16 117.6 . . ? C17 C16 H16 117.6 . . ? C18 C17 C16 114.3(3) . . ? C18 C17 C19 126.2(3) . . ? C16 C17 C19 119.4(3) . . ? N4 C18 C17 123.3(2) . . ? N4 C18 H18 118.3 . . ? C17 C18 H18 118.3 . . ? C20 C19 C28 118.9(3) . . ? C20 C19 C17 118.5(3) . . ? C28 C19 C17 122.5(3) . . ? C19 C20 C21 123.1(3) . . ? C19 C20 H20 118.5 . . ? C21 C20 H20 118.5 . . ? C22 C21 C20 118.8(3) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C21 C22 C23 120.6(3) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C24 121.6(3) . . ? C22 C23 C28 119.8(3) . . ? C24 C23 C28 118.6(3) . . ? C25 C24 C23 122.0(3) . . ? C25 C24 H24 119.0 . . ? C23 C24 H24 119.0 . . ? C24 C25 C26 119.8(3) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C27 C26 C25 121.1(3) . . ? C27 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? C26 C27 C28 120.6(3) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C19 C28 C27 123.4(3) . . ? C19 C28 C23 118.8(3) . . ? C27 C28 C23 117.8(3) . . ? F2 B1 F3 112.0(3) . . ? F2 B1 F4 112.0(3) . . ? F3 B1 F4 109.9(3) . . ? F2 B1 F1 107.9(3) . . ? F3 B1 F1 108.2(3) . . ? F4 B1 F1 106.6(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.721 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.074 #============================================================================== data_compound6+AgBF4 _database_code_depnum_ccdc_archive 'CCDC 693059' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C14 H11 N3) Ag, B F4 ' _chemical_formula_sum 'C28 H22 Ag B F4 N6' _chemical_formula_weight 637.20 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 21.7294(13) _cell_length_b 9.7649(6) _cell_length_c 12.1235(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.099(4) _cell_angle_gamma 90.00 _cell_volume 2546.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 21533 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 25.028 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.852 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9046 _exptl_absorpt_correction_T_max 0.9832 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23647 _diffrn_reflns_av_R_equivalents 0.137 _diffrn_reflns_av_sigmaI/netI 0.0987 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4484 _reflns_number_gt 2424 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0693P)^2^+34.1016P] 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 4484 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1629 _refine_ls_R_factor_gt 0.0909 _refine_ls_wR_factor_ref 0.2454 _refine_ls_wR_factor_gt 0.2069 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 0.49845(4) 0.24732(10) 0.85320(8) 0.0416(3) Uani 1 1 d . . . N1 N 0.5583(4) 0.4164(10) 0.8847(8) 0.042(2) Uani 1 1 d . . . N2 N 0.4779(5) 0.5704(11) 0.8692(8) 0.049(3) Uani 1 1 d . . . H2A H 0.4629 0.6533 0.8758 0.059 Uiso 1 1 calc R . . H2B H 0.4528 0.5029 0.8448 0.059 Uiso 1 1 calc R . . N3 N 0.5760(5) 0.6509(10) 0.9326(8) 0.045(2) Uani 1 1 d . . . N4 N 0.4357(5) 0.0792(10) 0.8525(8) 0.045(2) Uani 1 1 d . . . N5 N 0.5159(5) -0.0762(10) 0.8804(8) 0.049(3) Uani 1 1 d . . . H5A H 0.5303 -0.1599 0.8928 0.059 Uiso 1 1 calc R . . H5B H 0.5415 -0.0089 0.8707 0.059 Uiso 1 1 calc R . . N6 N 0.4168(5) -0.1532(11) 0.8909(9) 0.050(3) Uani 1 1 d . . . C1 C 0.5371(6) 0.5479(13) 0.8952(10) 0.041(3) Uiso 1 1 d . . . C2 C 0.6376(6) 0.6247(14) 0.9549(10) 0.049(3) Uiso 1 1 d . . . H2 H 0.6652 0.6978 0.9785 0.059 Uiso 1 1 calc R . . C3 C 0.6619(6) 0.4946(14) 0.9445(11) 0.050(3) Uiso 1 1 d . . . C4 C 0.6224(6) 0.3943(15) 0.9063(11) 0.055(4) Uiso 1 1 d . . . H4 H 0.6384 0.3061 0.8936 0.066 Uiso 1 1 calc R . . C5 C 0.7300(6) 0.4670(13) 0.9641(10) 0.042(3) Uiso 1 1 d . . . C6 C 0.7717(7) 0.5431(15) 1.0425(12) 0.061(4) Uiso 1 1 d . . . H6 H 0.7555 0.6120 1.0857 0.073 Uiso 1 1 calc R . . C7 C 0.8330(7) 0.5198(16) 1.0568(12) 0.063(4) Uiso 1 1 d . . . H7 H 0.8593 0.5718 1.1105 0.076 Uiso 1 1 calc R . . C8 C 0.8595(7) 0.4198(15) 0.9939(12) 0.058(4) Uiso 1 1 d . . . C9 C 0.9244(8) 0.3973(18) 1.0048(14) 0.078(5) Uiso 1 1 d . . . H9 H 0.9523 0.4529 1.0528 0.093 Uiso 1 1 calc R . . C10 C 0.9465(8) 0.2920(17) 0.9437(13) 0.077(5) Uiso 1 1 d . . . H10 H 0.9898 0.2728 0.9547 0.093 Uiso 1 1 calc R . . C11 C 0.9094(7) 0.2170(16) 0.8706(12) 0.068(4) Uiso 1 1 d . . . H11 H 0.9267 0.1502 0.8270 0.082 Uiso 1 1 calc R . . C12 C 0.8460(6) 0.2362(15) 0.8580(10) 0.053(3) Uiso 1 1 d . . . H12 H 0.8198 0.1802 0.8075 0.063 Uiso 1 1 calc R . . C13 C 0.8195(6) 0.3381(15) 0.9192(11) 0.054(3) Uiso 1 1 d . . . C14 C 0.7559(6) 0.3629(14) 0.9058(11) 0.050(3) Uiso 1 1 d . . . H14 H 0.7291 0.3075 0.8555 0.060 Uiso 1 1 calc R . . C15 C 0.4570(6) -0.0523(13) 0.8764(10) 0.040(3) Uiso 1 1 d . . . C16 C 0.3557(6) -0.1277(15) 0.8812(10) 0.052(3) Uiso 1 1 d . . . H16 H 0.3283 -0.2005 0.8929 0.062 Uiso 1 1 calc R . . C17 C 0.3309(6) 0.0003(13) 0.8547(10) 0.043(3) Uiso 1 1 d . . . C18 C 0.3757(6) 0.0989(14) 0.8391(10) 0.044(3) Uiso 1 1 d . . . H18 H 0.3611 0.1878 0.8169 0.053 Uiso 1 1 calc R . . C19 C 0.2630(6) 0.0330(14) 0.8399(11) 0.050(3) Uiso 1 1 d . . . C20 C 0.2229(7) -0.0445(16) 0.8975(12) 0.061(4) Uiso 1 1 d . . . H20 H 0.2391 -0.1154 0.9469 0.073 Uiso 1 1 calc R . . C21 C 0.1609(7) -0.0169(16) 0.8819(12) 0.065(4) Uiso 1 1 d . . . H21 H 0.1343 -0.0678 0.9223 0.078 Uiso 1 1 calc R . . C22 C 0.1354(7) 0.0845(16) 0.8077(12) 0.064(4) Uiso 1 1 d . . . C23 C 0.0704(8) 0.1195(18) 0.7892(14) 0.077(5) Uiso 1 1 d . . . H23 H 0.0419 0.0696 0.8263 0.092 Uiso 1 1 calc R . . C24 C 0.0488(8) 0.2270(18) 0.7166(13) 0.078(5) Uiso 1 1 d . . . H24 H 0.0060 0.2512 0.7060 0.094 Uiso 1 1 calc R . . C25 C 0.0893(8) 0.2951(18) 0.6624(14) 0.075(5) Uiso 1 1 d . . . H25 H 0.0741 0.3651 0.6113 0.090 Uiso 1 1 calc R . . C26 C 0.1515(6) 0.2670(15) 0.6784(11) 0.058(3) Uiso 1 1 d . . . H26 H 0.1782 0.3176 0.6380 0.069 Uiso 1 1 calc R . . C27 C 0.1766(6) 0.1659(15) 0.7525(11) 0.055(3) Uiso 1 1 d . . . C28 C 0.2401(6) 0.1326(13) 0.7694(10) 0.047(3) Uiso 1 1 d . . . H28 H 0.2677 0.1819 0.7297 0.056 Uiso 1 1 calc R . . B1 B 0.3347(7) 0.4958(17) 0.7034(15) 0.055(4) Uani 1 1 d . . . F1 F 0.3728(4) 0.4119(9) 0.7774(9) 0.087(3) Uani 1 1 d . . . F2 F 0.2994(6) 0.4129(12) 0.6314(10) 0.121(4) Uani 1 1 d . . . F3 F 0.3007(6) 0.5794(12) 0.7548(11) 0.125(4) Uani 1 1 d . . . F4 F 0.3725(4) 0.5769(9) 0.6435(8) 0.082(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 0.0418(5) 0.0274(4) 0.0557(5) -0.0008(5) 0.0067(3) -0.0013(5) N1 0.038(6) 0.041(6) 0.046(6) 0.003(5) 0.006(4) -0.005(5) N2 0.059(7) 0.033(6) 0.054(7) -0.006(5) 0.004(5) 0.009(5) N3 0.044(6) 0.037(6) 0.055(7) 0.000(5) 0.010(5) -0.004(5) N4 0.056(7) 0.029(5) 0.050(6) -0.003(5) 0.010(5) 0.003(5) N5 0.084(9) 0.022(5) 0.043(7) 0.008(4) 0.015(6) 0.018(6) N6 0.058(7) 0.034(6) 0.060(7) 0.003(5) 0.018(5) 0.002(5) B1 0.040(9) 0.045(9) 0.079(12) 0.013(9) -0.001(8) -0.001(8) F1 0.058(5) 0.060(6) 0.138(9) 0.035(6) -0.002(5) -0.015(5) F2 0.137(10) 0.092(8) 0.118(9) 0.016(7) -0.034(7) -0.044(8) F3 0.146(11) 0.089(8) 0.159(11) 0.022(8) 0.088(9) 0.028(8) F4 0.044(5) 0.064(6) 0.140(8) 0.042(6) 0.026(5) 0.009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N1 2.103(10) . ? Ag1 N4 2.133(10) . ? N1 C1 1.377(15) . ? N1 C4 1.396(16) . ? N2 C1 1.298(15) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 C1 1.351(15) . ? N3 C2 1.352(16) . ? N4 C18 1.305(15) . ? N4 C15 1.381(15) . ? N5 C15 1.294(15) . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? N6 C16 1.341(16) . ? N6 C15 1.344(16) . ? C2 C3 1.388(18) . ? C2 H2 0.9500 . ? C3 C4 1.341(18) . ? C3 C5 1.490(17) . ? C4 H4 0.9500 . ? C5 C14 1.401(17) . ? C5 C6 1.425(18) . ? C6 C7 1.339(19) . ? C6 H6 0.9500 . ? C7 C8 1.41(2) . ? C7 H7 0.9500 . ? C8 C13 1.410(19) . ? C8 C9 1.41(2) . ? C9 C10 1.39(2) . ? C9 H9 0.9500 . ? C10 C11 1.33(2) . ? C10 H10 0.9500 . ? C11 C12 1.376(19) . ? C11 H11 0.9500 . ? C12 C13 1.411(18) . ? C12 H12 0.9500 . ? C13 C14 1.391(18) . ? C14 H14 0.9500 . ? C16 C17 1.380(18) . ? C16 H16 0.9500 . ? C17 C18 1.401(17) . ? C17 C19 1.495(17) . ? C18 H18 0.9500 . ? C19 C28 1.344(17) . ? C19 C20 1.411(18) . ? C20 C21 1.361(19) . ? C20 H20 0.9500 . ? C21 C22 1.40(2) . ? C21 H21 0.9500 . ? C22 C27 1.433(19) . ? C22 C23 1.44(2) . ? C23 C24 1.41(2) . ? C23 H23 0.9500 . ? C24 C25 1.35(2) . ? C24 H24 0.9500 . ? C25 C26 1.37(2) . ? C25 H25 0.9500 . ? C26 C27 1.394(19) . ? C26 H26 0.9500 . ? C27 C28 1.404(18) . ? C28 H28 0.9500 . ? B1 F3 1.32(2) . ? B1 F2 1.348(19) . ? B1 F1 1.398(17) . ? B1 F4 1.412(18) . ? 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 N4 169.6(4) . . ? C1 N1 C4 117.7(11) . . ? C1 N1 Ag1 122.8(8) . . ? C4 N1 Ag1 119.2(9) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C1 N3 C2 118.8(11) . . ? C18 N4 C15 117.6(11) . . ? C18 N4 Ag1 120.9(8) . . ? C15 N4 Ag1 121.3(8) . . ? C15 N5 H5A 120.0 . . ? C15 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C16 N6 C15 120.4(11) . . ? N2 C1 N3 120.5(12) . . ? N2 C1 N1 118.0(11) . . ? N3 C1 N1 121.6(11) . . ? N3 C2 C3 122.3(12) . . ? N3 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C4 C3 C2 117.8(13) . . ? C4 C3 C5 119.7(12) . . ? C2 C3 C5 122.2(12) . . ? C3 C4 N1 121.7(13) . . ? C3 C4 H4 119.2 . . ? N1 C4 H4 119.2 . . ? C14 C5 C6 116.9(12) . . ? C14 C5 C3 120.8(12) . . ? C6 C5 C3 122.4(12) . . ? C7 C6 C5 121.7(14) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C8 121.5(15) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C7 C8 C13 118.5(13) . . ? C7 C8 C9 122.3(14) . . ? C13 C8 C9 119.1(14) . . ? C10 C9 C8 118.7(16) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? C11 C10 C9 122.6(17) . . ? C11 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? C10 C11 C12 120.1(16) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C13 120.9(14) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C8 119.2(13) . . ? C14 C13 C12 122.3(13) . . ? C8 C13 C12 118.5(13) . . ? C13 C14 C5 122.1(13) . . ? C13 C14 H14 119.0 . . ? C5 C14 H14 119.0 . . ? N5 C15 N6 121.3(12) . . ? N5 C15 N4 118.4(11) . . ? N6 C15 N4 120.3(11) . . ? N6 C16 C17 122.5(13) . . ? N6 C16 H16 118.7 . . ? C17 C16 H16 118.7 . . ? C16 C17 C18 113.5(11) . . ? C16 C17 C19 124.5(12) . . ? C18 C17 C19 122.0(12) . . ? N4 C18 C17 125.6(12) . . ? N4 C18 H18 117.2 . . ? C17 C18 H18 117.2 . . ? C28 C19 C20 120.2(13) . . ? C28 C19 C17 120.1(12) . . ? C20 C19 C17 119.6(12) . . ? C21 C20 C19 119.6(14) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 121.7(15) . . ? C20 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C21 C22 C27 118.4(14) . . ? C21 C22 C23 124.1(15) . . ? C27 C22 C23 117.4(14) . . ? C24 C23 C22 120.6(16) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C25 C24 C23 119.3(17) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 122.2(17) . . ? C24 C25 H25 118.9 . . ? C26 C25 H25 118.9 . . ? C25 C26 C27 121.6(14) . . ? C25 C26 H26 119.2 . . ? C27 C26 H26 119.2 . . ? C26 C27 C28 123.1(13) . . ? C26 C27 C22 118.7(13) . . ? C28 C27 C22 118.0(13) . . ? C19 C28 C27 121.9(13) . . ? C19 C28 H28 119.0 . . ? C27 C28 H28 119.0 . . ? F3 B1 F2 111.9(14) . . ? F3 B1 F1 112.4(15) . . ? F2 B1 F1 107.2(13) . . ? F3 B1 F4 107.5(13) . . ? F2 B1 F4 108.8(15) . . ? F1 B1 F4 108.9(11) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.407 _refine_diff_density_min -1.392 _refine_diff_density_rms 0.148 #===END