Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Hiromitsu Maeda' _publ_contact_author_address ; Department of Bioscience and Biotechnology, Faculty of Science and Engineering Ritsumeikan University 1-1-1 Nojihigashi Kusatsu Shiga 525-8577 JAPAN ; _publ_contact_author_email MAEDAHIR@SE.RITSUMEI.AC.JP _publ_section_title ; Dipyrrolylpyrazoles: anion receptors in protonated form and efficient building blocks for organized structures ; loop_ _publ_author_name 'Hiromitsu Maeda' 'Yoshihiro Ito' 'Yukio Kusunose' 'Takashi Nakanishi' # Attachment 'dipypyrazole_HMaeda_CIF.cif' data_dpp _database_code_depnum_ccdc_archive 'CCDC 625142' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 N4, C2 F3 O2' _chemical_formula_sum 'C13 H11 F3 N4 O2' _chemical_formula_weight 312.26 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 14.3569(10) _cell_length_b 15.2520(11) _cell_length_c 6.0571(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.1800(10) _cell_angle_gamma 90.00 _cell_volume 1326.05(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4748 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 27.88 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9346 _exptl_absorpt_correction_T_max 0.9731 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8027 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 28.19 _reflns_number_total 3018 _reflns_number_gt 2638 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0639P)^2^+0.4490P] 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 3018 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1228 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _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 C1 C 0.21219(12) 0.17754(10) 0.8187(3) 0.0254(3) Uani 1 1 d . . . H1 H 0.1694 0.2084 0.9075 0.031 Uiso 1 1 calc R . . C2 C 0.30659(12) 0.17307(10) 0.8544(3) 0.0255(3) Uani 1 1 d . . . H2 H 0.3409 0.2001 0.9716 0.031 Uiso 1 1 calc R . . C3 C 0.34331(11) 0.12093(10) 0.6848(2) 0.0232(3) Uani 1 1 d . . . H3 H 0.4070 0.1063 0.6665 0.028 Uiso 1 1 calc R . . C4 C 0.26948(10) 0.09512(10) 0.5502(2) 0.0187(3) Uani 1 1 d . . . C5 C 0.27052(10) 0.04257(9) 0.3519(2) 0.0181(3) Uani 1 1 d . . . C6 C 0.34444(10) -0.00132(10) 0.2566(2) 0.0196(3) Uani 1 1 d . . . H6 H 0.4069 -0.0037 0.3115 0.023 Uiso 1 1 calc R . . C7 C 0.30945(10) -0.04104(9) 0.0653(2) 0.0181(3) Uani 1 1 d . . . C8 C 0.35766(10) -0.09400(10) -0.0937(2) 0.0187(3) Uani 1 1 d . . . C9 C 0.45113(11) -0.11430(10) -0.1001(3) 0.0226(3) Uani 1 1 d . . . H9 H 0.4981 -0.0954 0.0020 0.027 Uiso 1 1 calc R . . C10 C 0.46423(11) -0.16812(10) -0.2859(3) 0.0246(3) Uani 1 1 d . . . H10A H 0.5216 -0.1924 -0.3320 0.029 Uiso 1 1 calc R . . C11 C 0.37876(11) -0.17898(10) -0.3879(3) 0.0231(3) Uani 1 1 d . . . H11A H 0.3666 -0.2122 -0.5180 0.028 Uiso 1 1 calc R . . C12 C 0.06687(11) 0.83842(11) 0.3833(3) 0.0236(3) Uani 1 1 d . . . C13 C 0.05188(10) 0.89393(9) 0.5948(2) 0.0189(3) Uani 1 1 d . . . F1 F 0.15459(8) 0.81389(8) 0.35715(19) 0.0455(3) Uani 1 1 d . . . F2 F 0.01387(8) 0.76652(7) 0.38209(16) 0.0365(3) Uani 1 1 d . . . F3 F 0.04182(7) 0.88442(7) 0.20324(15) 0.0331(3) Uani 1 1 d . . . N1 N 0.19004(9) 0.13017(8) 0.6343(2) 0.0218(3) Uani 1 1 d . . . H1N H 0.1335 0.1232 0.5781 0.026 Uiso 1 1 calc R . . N2 N 0.19458(9) 0.02869(8) 0.22247(19) 0.0185(3) Uani 1 1 d . . . H2N H 0.1385 0.0493 0.2467 0.022 Uiso 1 1 calc R . . N3 N 0.21827(8) -0.02209(8) 0.0492(2) 0.0188(3) Uani 1 1 d . . . H3N H 0.1800 -0.0398 -0.0571 0.023 Uiso 1 1 calc R . . N4 N 0.31431(9) -0.13399(8) -0.2710(2) 0.0204(3) Uani 1 1 d . . . H4N H 0.2544 -0.1310 -0.3039 0.024 Uiso 1 1 calc R . . O1 O 0.12373(7) 0.91708(8) 0.69497(18) 0.0253(3) Uani 1 1 d . . . O2 O -0.03088(7) 0.90860(8) 0.63279(18) 0.0248(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 C1 0.0372(9) 0.0206(7) 0.0185(7) -0.0039(6) 0.0010(6) -0.0006(6) C2 0.0375(9) 0.0213(7) 0.0176(7) -0.0007(6) -0.0037(6) -0.0082(6) C3 0.0264(8) 0.0244(8) 0.0186(7) 0.0019(6) -0.0023(6) -0.0037(6) C4 0.0230(7) 0.0171(7) 0.0159(7) 0.0019(5) -0.0005(5) -0.0011(5) C5 0.0211(7) 0.0171(7) 0.0159(7) 0.0034(5) -0.0013(5) -0.0031(5) C6 0.0195(7) 0.0204(7) 0.0187(7) 0.0018(6) -0.0014(5) -0.0008(5) C7 0.0185(7) 0.0180(7) 0.0179(7) 0.0033(5) 0.0004(5) -0.0016(5) C8 0.0206(7) 0.0175(7) 0.0181(7) 0.0016(5) 0.0006(5) -0.0010(5) C9 0.0199(7) 0.0236(8) 0.0242(8) 0.0009(6) 0.0002(6) -0.0007(6) C10 0.0227(8) 0.0246(8) 0.0266(8) 0.0018(6) 0.0064(6) 0.0040(6) C11 0.0279(8) 0.0221(8) 0.0194(7) -0.0007(6) 0.0039(6) 0.0033(6) C12 0.0257(8) 0.0241(8) 0.0210(7) -0.0044(6) 0.0008(6) 0.0004(6) C13 0.0236(7) 0.0169(7) 0.0161(7) -0.0008(5) -0.0010(5) 0.0021(5) F1 0.0342(6) 0.0605(8) 0.0417(7) -0.0241(6) 0.0018(5) 0.0160(5) F2 0.0587(7) 0.0227(5) 0.0284(6) -0.0078(4) 0.0062(5) -0.0117(5) F3 0.0482(6) 0.0339(6) 0.0171(5) -0.0008(4) -0.0012(4) -0.0070(4) N1 0.0245(7) 0.0218(6) 0.0190(6) -0.0040(5) -0.0021(5) 0.0003(5) N2 0.0193(6) 0.0204(6) 0.0159(6) -0.0029(5) 0.0008(4) 0.0008(5) N3 0.0195(6) 0.0211(6) 0.0157(6) -0.0044(5) -0.0001(4) -0.0001(5) N4 0.0201(6) 0.0216(6) 0.0193(6) -0.0021(5) -0.0005(5) 0.0020(5) O1 0.0220(6) 0.0312(6) 0.0225(6) -0.0073(5) -0.0027(4) -0.0003(4) O2 0.0208(5) 0.0293(6) 0.0243(6) -0.0056(5) -0.0011(4) 0.0042(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 C1 N1 1.3623(19) . ? C1 C2 1.370(2) . ? C1 H1 0.9500 . ? C2 C3 1.410(2) . ? C2 H2 0.9500 . ? C3 C4 1.381(2) . ? C3 H3 0.9500 . ? C4 N1 1.3674(19) . ? C4 C5 1.445(2) . ? C5 N2 1.3463(18) . ? C5 C6 1.390(2) . ? C6 C7 1.392(2) . ? C6 H6 0.9500 . ? C7 N3 1.3422(19) . ? C7 C8 1.445(2) . ? C8 N4 1.3730(19) . ? C8 C9 1.379(2) . ? C9 C10 1.408(2) . ? C9 H9 0.9500 . ? C10 C11 1.373(2) . ? C10 H10A 0.9500 . ? C11 N4 1.3621(19) . ? C11 H11A 0.9500 . ? C12 F1 1.3263(19) . ? C12 F2 1.3346(19) . ? C12 F3 1.3395(18) . ? C12 C13 1.554(2) . ? C13 O2 1.2354(18) . ? C13 O1 1.2373(18) . ? N1 H1N 0.8800 . ? N2 N3 1.3535(17) . ? N2 H2N 0.8800 . ? N3 H3N 0.8800 . ? N4 H4N 0.8800 . ? 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 C1 C2 108.45(14) . . ? N1 C1 H1 125.8 . . ? C2 C1 H1 125.8 . . ? C1 C2 C3 107.27(14) . . ? C1 C2 H2 126.4 . . ? C3 C2 H2 126.4 . . ? C4 C3 C2 107.26(14) . . ? C4 C3 H3 126.4 . . ? C2 C3 H3 126.4 . . ? N1 C4 C3 107.74(13) . . ? N1 C4 C5 123.34(13) . . ? C3 C4 C5 128.91(14) . . ? N2 C5 C6 107.37(13) . . ? N2 C5 C4 123.32(13) . . ? C6 C5 C4 129.31(13) . . ? C5 C6 C7 106.83(13) . . ? C5 C6 H6 126.6 . . ? C7 C6 H6 126.6 . . ? N3 C7 C6 107.57(13) . . ? N3 C7 C8 123.48(13) . . ? C6 C7 C8 128.95(13) . . ? N4 C8 C9 107.69(13) . . ? N4 C8 C7 123.67(13) . . ? C9 C8 C7 128.64(14) . . ? C8 C9 C10 107.43(13) . . ? C8 C9 H9 126.3 . . ? C10 C9 H9 126.3 . . ? C11 C10 C9 107.29(14) . . ? C11 C10 H10A 126.4 . . ? C9 C10 H10A 126.4 . . ? N4 C11 C10 108.40(14) . . ? N4 C11 H11A 125.8 . . ? C10 C11 H11A 125.8 . . ? F1 C12 F2 108.07(14) . . ? F1 C12 F3 106.88(13) . . ? F2 C12 F3 106.41(12) . . ? F1 C12 C13 113.57(13) . . ? F2 C12 C13 111.30(12) . . ? F3 C12 C13 110.26(12) . . ? O2 C13 O1 130.72(14) . . ? O2 C13 C12 113.71(13) . . ? O1 C13 C12 115.56(13) . . ? C1 N1 C4 109.28(13) . . ? C1 N1 H1N 125.4 . . ? C4 N1 H1N 125.4 . . ? C5 N2 N3 109.15(12) . . ? C5 N2 H2N 125.4 . . ? N3 N2 H2N 125.4 . . ? C7 N3 N2 109.08(12) . . ? C7 N3 H3N 125.5 . . ? N2 N3 H3N 125.5 . . ? C11 N4 C8 109.19(13) . . ? C11 N4 H4N 125.4 . . ? C8 N4 H4N 125.4 . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 28.19 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.370 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.091 #============================================================================== # End of CIF #============================================================================== data_shelxl_1 _database_code_depnum_ccdc_archive 'CCDC 625143' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 F3 N4 O2' _chemical_formula_weight 340.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.307(5) _cell_length_b 9.278(6) _cell_length_c 10.960(8) _cell_angle_alpha 85.90(3) _cell_angle_beta 87.73(3) _cell_angle_gamma 65.63(2) _cell_volume 767.5(9) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6116 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.6 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9401 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7620 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3484 _reflns_number_gt 2811 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.6.0' _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^)+(0.0919P)^2^+0.9204P] 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 3484 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1866 _refine_ls_wR_factor_gt 0.1748 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 F1 F 0.5081(3) 0.2857(3) 0.08507(17) 0.0567(6) Uani 1 1 d . . . F2 F 0.2366(2) 0.3446(3) 0.12887(19) 0.0609(7) Uani 1 1 d . . . F3 F 0.4329(3) 0.1189(2) 0.1849(2) 0.0543(6) Uani 1 1 d . . . O1 O 0.3007(2) 0.4599(2) 0.32202(16) 0.0239(4) Uani 1 1 d . . . O2 O 0.5667(2) 0.2546(2) 0.34241(16) 0.0254(4) Uani 1 1 d . . . N1 N 0.0836(2) 0.4338(2) 0.70214(17) 0.0175(4) Uani 1 1 d . . . H1 H -0.0306 0.4734 0.7182 0.021 Uiso 1 1 calc R . . N2 N -0.0947(2) 0.3190(2) 0.52412(17) 0.0173(4) Uani 1 1 d . . . H2 H -0.1739 0.3944 0.5659 0.021 Uiso 1 1 calc R . . N3 N -0.1306(2) 0.2368(2) 0.43964(17) 0.0177(4) Uani 1 1 d . . . H3 H -0.2370 0.2497 0.4186 0.021 Uiso 1 1 calc R . . N4 N -0.1092(2) 0.0178(2) 0.24727(17) 0.0182(4) Uani 1 1 d . . . H4 H -0.2205 0.0748 0.2661 0.022 Uiso 1 1 calc R . . C1 C 0.1560(3) 0.5766(3) 0.8622(2) 0.0253(5) Uani 1 1 d . . . H1A H 0.0282 0.6180 0.8769 0.030 Uiso 1 1 calc R . . H1B H 0.1895 0.6649 0.8402 0.030 Uiso 1 1 calc R . . H1C H 0.2180 0.5186 0.9365 0.030 Uiso 1 1 calc R . . C2 C 0.2051(3) 0.4680(3) 0.7605(2) 0.0191(5) Uani 1 1 d . . . C3 C 0.3682(3) 0.3836(3) 0.7089(2) 0.0222(5) Uani 1 1 d . . . H3A H 0.4769 0.3849 0.7313 0.027 Uiso 1 1 calc R . . C4 C 0.3458(3) 0.2949(3) 0.6173(2) 0.0215(5) Uani 1 1 d . . . H4A H 0.4362 0.2255 0.5669 0.026 Uiso 1 1 calc R . . C5 C 0.1682(3) 0.3276(3) 0.6141(2) 0.0180(4) Uani 1 1 d . . . C6 C 0.0815(3) 0.2667(2) 0.5336(2) 0.0166(4) Uani 1 1 d . . . C7 C 0.1592(3) 0.1485(3) 0.4515(2) 0.0193(5) Uani 1 1 d . . . H7A H 0.2822 0.0900 0.4379 0.023 Uiso 1 1 calc R . . C8 C 0.0221(3) 0.1324(2) 0.3930(2) 0.0174(4) Uani 1 1 d . . . C9 C 0.0343(3) 0.0264(3) 0.3000(2) 0.0182(4) Uani 1 1 d . . . C10 C 0.1842(3) -0.0813(3) 0.2462(2) 0.0227(5) Uani 1 1 d . . . H10A H 0.3027 -0.1012 0.2642 0.027 Uiso 1 1 calc R . . C11 C 0.1297(3) -0.1564(3) 0.1597(2) 0.0242(5) Uani 1 1 d . . . H11A H 0.2050 -0.2368 0.1091 0.029 Uiso 1 1 calc R . . C12 C -0.0524(3) -0.0925(3) 0.1615(2) 0.0206(5) Uani 1 1 d . . . C13 C -0.1780(3) -0.1266(3) 0.0876(2) 0.0260(5) Uani 1 1 d . . . H13A H -0.2996 -0.0596 0.1118 0.031 Uiso 1 1 calc R . . H13B H -0.1568 -0.2384 0.1018 0.031 Uiso 1 1 calc R . . H13C H -0.1602 -0.1040 0.0006 0.031 Uiso 1 1 calc R . . C14 C 0.4234(3) 0.3366(3) 0.2920(2) 0.0190(5) Uani 1 1 d . . . C15 C 0.3987(3) 0.2727(3) 0.1710(2) 0.0268(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 F1 0.0653(13) 0.0948(17) 0.0281(9) -0.0223(10) 0.0179(9) -0.0499(13) F2 0.0308(9) 0.0836(15) 0.0495(12) -0.0355(11) -0.0177(8) 0.0017(10) F3 0.0755(14) 0.0401(10) 0.0577(13) -0.0223(9) -0.0027(10) -0.0310(10) O1 0.0178(8) 0.0236(8) 0.0279(9) -0.0090(7) 0.0014(6) -0.0050(7) O2 0.0162(8) 0.0296(9) 0.0282(9) -0.0097(7) -0.0034(6) -0.0056(7) N1 0.0162(9) 0.0176(9) 0.0188(9) -0.0027(7) -0.0008(7) -0.0067(7) N2 0.0163(9) 0.0161(8) 0.0185(9) -0.0050(7) -0.0007(7) -0.0052(7) N3 0.0164(9) 0.0182(9) 0.0187(9) -0.0042(7) -0.0028(7) -0.0066(7) N4 0.0179(9) 0.0173(9) 0.0184(9) -0.0043(7) -0.0002(7) -0.0057(7) C1 0.0298(12) 0.0254(12) 0.0236(12) -0.0064(9) -0.0005(9) -0.0134(10) C2 0.0199(10) 0.0175(10) 0.0214(11) 0.0004(8) -0.0036(8) -0.0093(9) C3 0.0189(10) 0.0228(11) 0.0266(12) -0.0018(9) -0.0036(9) -0.0100(9) C4 0.0180(11) 0.0209(11) 0.0243(11) -0.0035(9) -0.0001(8) -0.0063(9) C5 0.0180(10) 0.0160(10) 0.0188(10) -0.0013(8) -0.0006(8) -0.0058(8) C6 0.0172(10) 0.0147(9) 0.0173(10) 0.0010(8) -0.0015(8) -0.0063(8) C7 0.0166(10) 0.0181(10) 0.0207(11) -0.0019(8) -0.0014(8) -0.0046(8) C8 0.0181(10) 0.0151(9) 0.0167(10) 0.0003(8) -0.0007(8) -0.0046(8) C9 0.0191(10) 0.0167(10) 0.0176(10) -0.0009(8) -0.0020(8) -0.0061(8) C10 0.0199(11) 0.0206(11) 0.0248(12) -0.0040(9) 0.0000(9) -0.0051(9) C11 0.0262(12) 0.0193(11) 0.0240(12) -0.0076(9) 0.0045(9) -0.0056(9) C12 0.0276(12) 0.0169(10) 0.0169(10) -0.0025(8) 0.0003(9) -0.0087(9) C13 0.0309(12) 0.0255(12) 0.0227(12) -0.0073(9) -0.0021(9) -0.0116(10) C14 0.0167(10) 0.0209(10) 0.0214(11) -0.0046(8) 0.0014(8) -0.0094(9) C15 0.0197(11) 0.0330(13) 0.0257(12) -0.0115(10) 0.0000(9) -0.0073(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 F1 C15 1.317(3) . ? F2 C15 1.318(3) . ? F3 C15 1.334(3) . ? O1 C14 1.233(3) . ? O2 C14 1.243(3) . ? N1 C2 1.369(3) . ? N1 C5 1.381(3) . ? N1 H1 0.8800 . ? N2 C6 1.344(3) . ? N2 N3 1.356(3) . ? N2 H2 0.8800 . ? N3 C8 1.347(3) . ? N3 H3 0.8800 . ? N4 C12 1.363(3) . ? N4 C9 1.378(3) . ? N4 H4 0.8800 . ? C1 C2 1.487(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.377(3) . ? C3 C4 1.407(3) . ? C3 H3A 0.9500 . ? C4 C5 1.379(3) . ? C4 H4A 0.9500 . ? C5 C6 1.440(3) . ? C6 C7 1.393(3) . ? C7 C8 1.393(3) . ? C7 H7A 0.9500 . ? C8 C9 1.439(3) . ? C9 C10 1.377(3) . ? C10 C11 1.406(3) . ? C10 H10A 0.9500 . ? C11 C12 1.378(3) . ? C11 H11A 0.9500 . ? C12 C13 1.490(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.545(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 109.37(19) . . ? C2 N1 H1 125.3 . . ? C5 N1 H1 125.3 . . ? C6 N2 N3 108.95(18) . . ? C6 N2 H2 125.5 . . ? N3 N2 H2 125.5 . . ? C8 N3 N2 109.39(18) . . ? C8 N3 H3 125.3 . . ? N2 N3 H3 125.3 . . ? C12 N4 C9 109.63(19) . . ? C12 N4 H4 125.2 . . ? C9 N4 H4 125.2 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 107.7(2) . . ? N1 C2 C1 122.5(2) . . ? C3 C2 C1 129.8(2) . . ? C2 C3 C4 108.0(2) . . ? C2 C3 H3A 126.0 . . ? C4 C3 H3A 126.0 . . ? C5 C4 C3 107.3(2) . . ? C5 C4 H4A 126.4 . . ? C3 C4 H4A 126.4 . . ? C4 C5 N1 107.65(19) . . ? C4 C5 C6 127.5(2) . . ? N1 C5 C6 124.8(2) . . ? N2 C6 C7 107.54(19) . . ? N2 C6 C5 124.5(2) . . ? C7 C6 C5 128.0(2) . . ? C6 C7 C8 106.9(2) . . ? C6 C7 H7A 126.5 . . ? C8 C7 H7A 126.5 . . ? N3 C8 C7 107.2(2) . . ? N3 C8 C9 124.6(2) . . ? C7 C8 C9 128.2(2) . . ? C10 C9 N4 107.5(2) . . ? C10 C9 C8 128.2(2) . . ? N4 C9 C8 124.4(2) . . ? C9 C10 C11 107.4(2) . . ? C9 C10 H10A 126.3 . . ? C11 C10 H10A 126.3 . . ? C12 C11 C10 107.8(2) . . ? C12 C11 H11A 126.1 . . ? C10 C11 H11A 126.1 . . ? N4 C12 C11 107.6(2) . . ? N4 C12 C13 122.0(2) . . ? C11 C12 C13 130.4(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 C14 O2 130.8(2) . . ? O1 C14 C15 115.6(2) . . ? O2 C14 C15 113.6(2) . . ? F1 C15 F2 108.2(2) . . ? F1 C15 F3 106.1(2) . . ? F2 C15 F3 106.3(2) . . ? F1 C15 C14 111.6(2) . . ? F2 C15 C14 113.0(2) . . ? F3 C15 C14 111.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N2 N3 C8 -0.8(2) . . . . ? C5 N1 C2 C3 0.3(2) . . . . ? C5 N1 C2 C1 -178.7(2) . . . . ? N1 C2 C3 C4 -0.4(3) . . . . ? C1 C2 C3 C4 178.6(2) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C4 C5 N1 -0.1(3) . . . . ? C3 C4 C5 C6 178.8(2) . . . . ? C2 N1 C5 C4 -0.1(2) . . . . ? C2 N1 C5 C6 -179.1(2) . . . . ? N3 N2 C6 C7 0.5(2) . . . . ? N3 N2 C6 C5 179.59(19) . . . . ? C4 C5 C6 N2 -170.7(2) . . . . ? N1 C5 C6 N2 8.0(3) . . . . ? C4 C5 C6 C7 8.1(4) . . . . ? N1 C5 C6 C7 -173.1(2) . . . . ? N2 C6 C7 C8 -0.1(2) . . . . ? C5 C6 C7 C8 -179.1(2) . . . . ? N2 N3 C8 C7 0.7(2) . . . . ? N2 N3 C8 C9 -179.3(2) . . . . ? C6 C7 C8 N3 -0.3(2) . . . . ? C6 C7 C8 C9 179.7(2) . . . . ? C12 N4 C9 C10 -0.2(2) . . . . ? C12 N4 C9 C8 179.1(2) . . . . ? N3 C8 C9 C10 178.8(2) . . . . ? C7 C8 C9 C10 -1.2(4) . . . . ? N3 C8 C9 N4 -0.4(4) . . . . ? C7 C8 C9 N4 179.6(2) . . . . ? N4 C9 C10 C11 -0.2(3) . . . . ? C8 C9 C10 C11 -179.4(2) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C9 N4 C12 C11 0.5(3) . . . . ? C9 N4 C12 C13 -179.1(2) . . . . ? C10 C11 C12 N4 -0.6(3) . . . . ? C10 C11 C12 C13 178.9(2) . . . . ? O1 C14 C15 F1 110.9(3) . . . . ? O2 C14 C15 F1 -68.3(3) . . . . ? O1 C14 C15 F2 -11.2(3) . . . . ? O2 C14 C15 F2 169.6(2) . . . . ? O1 C14 C15 F3 -130.8(2) . . . . ? O2 C14 C15 F3 50.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.681 _refine_diff_density_min -0.755 _refine_diff_density_rms 0.094 #============================================================================== # End of CIF #============================================================================== data_shelxl_2 _database_code_depnum_ccdc_archive 'CCDC 625144' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H7 F4 N4, C2 F3 O2' _chemical_formula_sum 'C13 H7 F7 N4 O2' _chemical_formula_weight 384.23 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.200(4) _cell_length_b 24.567(11) _cell_length_c 8.844(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.441(19) _cell_angle_gamma 90.00 _cell_volume 1456.1(12) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 9333 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.6 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.753 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.181 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9072 _exptl_absorpt_correction_T_max 0.9478 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12803 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3170 _reflns_number_gt 2480 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.6.0' _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^)+(0.0793P)^2^+2.7463P] 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 3170 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0822 _refine_ls_R_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.1870 _refine_ls_wR_factor_gt 0.1768 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 F1 F 1.2060(3) -0.17442(8) 0.8604(2) 0.0393(5) Uani 1 1 d . . . F2 F 1.0586(3) -0.06162(8) 0.8675(2) 0.0411(5) Uani 1 1 d . . . F3 F 0.7671(4) 0.11206(8) 0.8279(2) 0.0449(6) Uani 1 1 d . . . F4 F 0.5966(4) 0.22350(8) 0.7739(2) 0.0456(6) Uani 1 1 d . . . F5 F 0.1732(6) 0.19664(11) -0.1803(3) 0.0970(14) Uani 1 1 d . . . F6 F 0.3848(4) 0.21013(9) 0.0541(4) 0.0791(10) Uani 1 1 d . . . F7 F 0.1075(5) 0.17994(10) 0.0262(5) 0.0836(11) Uani 1 1 d . . . O1 O 0.3016(4) 0.09577(9) -0.1576(3) 0.0385(6) Uani 1 1 d . . . O2 O 0.4003(4) 0.09920(9) 0.1134(3) 0.0347(6) Uani 1 1 d . . . N1 N 0.9046(4) -0.12178(9) 0.4828(3) 0.0231(5) Uani 1 1 d . . . H1 H 0.8427 -0.1228 0.3767 0.028 Uiso 1 1 calc R . . N2 N 0.7012(4) -0.01612(9) 0.3654(3) 0.0201(5) Uani 1 1 d . . . H2 H 0.6882 -0.0379 0.2833 0.024 Uiso 1 1 calc R . . N3 N 0.6231(4) 0.03469(9) 0.3539(3) 0.0203(5) Uani 1 1 d . . . H3 H 0.5512 0.0511 0.2629 0.024 Uiso 1 1 calc R . . N4 N 0.5050(4) 0.14621(9) 0.4223(3) 0.0222(5) Uani 1 1 d . . . H4 H 0.4554 0.1403 0.3169 0.027 Uiso 1 1 calc R . . C1 C 1.0155(5) -0.16324(12) 0.5747(4) 0.0272(7) Uani 1 1 d . . . H1A H 1.0386 -0.1977 0.5361 0.033 Uiso 1 1 calc R . . C2 C 1.0872(5) -0.14600(12) 0.7323(4) 0.0262(6) Uani 1 1 d . . . C3 C 1.0180(5) -0.09321(12) 0.7359(3) 0.0255(6) Uani 1 1 d . . . C4 C 0.9034(4) -0.07818(11) 0.5797(3) 0.0207(6) Uani 1 1 d . . . C5 C 0.8018(4) -0.02763(11) 0.5232(3) 0.0194(6) Uani 1 1 d . . . C6 C 0.7869(4) 0.01728(11) 0.6140(3) 0.0210(6) Uani 1 1 d . . . H6 H 0.8433 0.0209 0.7289 0.025 Uiso 1 1 calc R . . C7 C 0.6731(4) 0.05585(11) 0.5036(3) 0.0190(6) Uani 1 1 d . . . C8 C 0.6149(4) 0.10930(11) 0.5361(3) 0.0201(6) Uani 1 1 d . . . C9 C 0.6620(5) 0.13434(12) 0.6844(3) 0.0263(6) Uani 1 1 d . . . C10 C 0.5817(5) 0.18673(12) 0.6581(4) 0.0283(7) Uani 1 1 d . . . C11 C 0.4834(5) 0.19316(11) 0.4947(4) 0.0257(6) Uani 1 1 d . . . H11 H 0.4129 0.2247 0.4417 0.031 Uiso 1 1 calc R . . C12 C 0.3257(5) 0.11764(12) -0.0261(3) 0.0264(6) Uani 1 1 d . . . C13 C 0.2482(5) 0.17681(12) -0.0348(3) 0.0254(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0405(12) 0.0365(11) 0.0335(10) 0.0144(8) 0.0049(8) 0.0134(9) F2 0.0537(14) 0.0372(11) 0.0217(9) -0.0022(7) 0.0012(8) 0.0088(9) F3 0.0624(15) 0.0397(11) 0.0198(9) -0.0026(8) -0.0001(9) 0.0151(10) F4 0.0604(15) 0.0337(11) 0.0336(11) -0.0161(8) 0.0065(10) 0.0091(9) F5 0.194(4) 0.0514(16) 0.0341(13) 0.0146(11) 0.0277(17) 0.064(2) F6 0.0517(17) 0.0277(12) 0.124(3) -0.0101(13) -0.0081(16) 0.0015(10) F7 0.097(2) 0.0399(14) 0.158(3) 0.0203(16) 0.098(2) 0.0200(14) O1 0.0610(18) 0.0298(12) 0.0223(11) -0.0017(8) 0.0125(10) 0.0115(11) O2 0.0520(16) 0.0272(11) 0.0195(10) 0.0025(8) 0.0068(10) 0.0096(10) N1 0.0267(14) 0.0215(12) 0.0223(12) 0.0037(9) 0.0103(10) 0.0029(9) N2 0.0240(13) 0.0174(11) 0.0183(11) 0.0002(8) 0.0072(9) 0.0008(9) N3 0.0227(13) 0.0176(11) 0.0200(11) 0.0015(8) 0.0071(9) 0.0016(9) N4 0.0259(14) 0.0190(11) 0.0205(11) -0.0005(9) 0.0069(9) -0.0009(9) C1 0.0280(17) 0.0223(14) 0.0333(16) 0.0062(11) 0.0134(13) 0.0059(11) C2 0.0211(16) 0.0289(15) 0.0265(15) 0.0103(11) 0.0062(11) 0.0049(11) C3 0.0237(16) 0.0285(15) 0.0228(14) 0.0025(11) 0.0067(11) 0.0008(11) C4 0.0196(15) 0.0202(13) 0.0233(13) 0.0027(10) 0.0090(11) -0.0006(10) C5 0.0170(14) 0.0210(13) 0.0201(13) 0.0031(10) 0.0068(10) -0.0022(10) C6 0.0194(15) 0.0231(13) 0.0192(13) 0.0006(10) 0.0057(10) -0.0013(10) C7 0.0171(14) 0.0204(13) 0.0208(13) -0.0014(10) 0.0083(10) -0.0038(10) C8 0.0189(15) 0.0197(13) 0.0219(13) -0.0006(10) 0.0077(10) -0.0019(10) C9 0.0289(17) 0.0263(14) 0.0205(14) -0.0007(10) 0.0053(11) 0.0009(11) C10 0.0312(18) 0.0237(14) 0.0282(15) -0.0084(11) 0.0088(12) -0.0014(12) C11 0.0302(17) 0.0171(13) 0.0297(15) -0.0011(11) 0.0109(12) -0.0003(11) C12 0.0331(18) 0.0228(14) 0.0225(14) 0.0001(11) 0.0091(12) 0.0027(12) C13 0.0302(17) 0.0234(14) 0.0238(14) 0.0017(11) 0.0114(12) 0.0023(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C2 1.339(3) . ? F2 C3 1.339(4) . ? F3 C9 1.335(3) . ? F4 C10 1.340(3) . ? F5 C13 1.294(4) . ? F6 C13 1.300(4) . ? F7 C13 1.313(4) . ? O1 C12 1.235(4) . ? O2 C12 1.238(4) . ? N1 C1 1.364(4) . ? N1 C4 1.374(4) . ? N1 H1 0.8800 . ? N2 C5 1.346(4) . ? N2 N3 1.357(3) . ? N2 H2 0.8800 . ? N3 C7 1.343(4) . ? N3 H3 0.8800 . ? N4 C11 1.355(4) . ? N4 C8 1.371(4) . ? N4 H4 0.8800 . ? C1 C2 1.365(4) . ? C1 H1A 0.9500 . ? C2 C3 1.394(4) . ? C3 C4 1.376(4) . ? C4 C5 1.435(4) . ? C5 C6 1.392(4) . ? C6 C7 1.392(4) . ? C6 H6 0.9500 . ? C7 C8 1.439(4) . ? C8 C9 1.374(4) . ? C9 C10 1.395(4) . ? C10 C11 1.367(4) . ? C11 H11 0.9500 . ? C12 C13 1.549(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 C1 N1 C4 110.3(2) . . ? C1 N1 H1 124.9 . . ? C4 N1 H1 124.9 . . ? C5 N2 N3 108.8(2) . . ? C5 N2 H2 125.6 . . ? N3 N2 H2 125.6 . . ? C7 N3 N2 109.1(2) . . ? C7 N3 H3 125.4 . . ? N2 N3 H3 125.4 . . ? C11 N4 C8 110.6(2) . . ? C11 N4 H4 124.7 . . ? C8 N4 H4 124.7 . . ? N1 C1 C2 107.3(3) . . ? N1 C1 H1A 126.4 . . ? C2 C1 H1A 126.4 . . ? F1 C2 C1 126.0(3) . . ? F1 C2 C3 126.1(3) . . ? C1 C2 C3 107.9(2) . . ? F2 C3 C4 125.3(3) . . ? F2 C3 C2 126.4(3) . . ? C4 C3 C2 108.4(3) . . ? N1 C4 C3 106.2(2) . . ? N1 C4 C5 125.2(2) . . ? C3 C4 C5 128.6(3) . . ? N2 C5 C6 107.8(2) . . ? N2 C5 C4 123.7(2) . . ? C6 C5 C4 128.4(3) . . ? C5 C6 C7 106.5(2) . . ? C5 C6 H6 126.7 . . ? C7 C6 H6 126.7 . . ? N3 C7 C6 107.8(2) . . ? N3 C7 C8 123.9(2) . . ? C6 C7 C8 128.4(3) . . ? N4 C8 C9 106.2(2) . . ? N4 C8 C7 126.1(2) . . ? C9 C8 C7 127.7(3) . . ? F3 C9 C8 125.5(3) . . ? F3 C9 C10 126.4(3) . . ? C8 C9 C10 108.2(3) . . ? F4 C10 C11 126.6(3) . . ? F4 C10 C9 125.6(3) . . ? C11 C10 C9 107.8(3) . . ? N4 C11 C10 107.3(3) . . ? N4 C11 H11 126.4 . . ? C10 C11 H11 126.4 . . ? O1 C12 O2 129.8(3) . . ? O1 C12 C13 115.9(3) . . ? O2 C12 C13 114.2(3) . . ? F5 C13 F6 108.2(3) . . ? F5 C13 F7 106.4(3) . . ? F6 C13 F7 104.0(3) . . ? F5 C13 C12 114.5(3) . . ? F6 C13 C12 112.4(3) . . ? F7 C13 C12 110.7(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N2 N3 C7 0.0(3) . . . . ? C4 N1 C1 C2 -0.3(4) . . . . ? N1 C1 C2 F1 -178.7(3) . . . . ? N1 C1 C2 C3 0.1(4) . . . . ? F1 C2 C3 F2 0.2(6) . . . . ? C1 C2 C3 F2 -178.6(3) . . . . ? F1 C2 C3 C4 178.9(3) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C1 N1 C4 C3 0.3(3) . . . . ? C1 N1 C4 C5 179.8(3) . . . . ? F2 C3 C4 N1 178.5(3) . . . . ? C2 C3 C4 N1 -0.2(3) . . . . ? F2 C3 C4 C5 -1.0(5) . . . . ? C2 C3 C4 C5 -179.7(3) . . . . ? N3 N2 C5 C6 0.0(3) . . . . ? N3 N2 C5 C4 179.9(3) . . . . ? N1 C4 C5 N2 -2.9(5) . . . . ? C3 C4 C5 N2 176.5(3) . . . . ? N1 C4 C5 C6 177.1(3) . . . . ? C3 C4 C5 C6 -3.5(5) . . . . ? N2 C5 C6 C7 0.1(3) . . . . ? C4 C5 C6 C7 -179.9(3) . . . . ? N2 N3 C7 C6 0.1(3) . . . . ? N2 N3 C7 C8 180.0(3) . . . . ? C5 C6 C7 N3 -0.1(3) . . . . ? C5 C6 C7 C8 -180.0(3) . . . . ? C11 N4 C8 C9 0.3(3) . . . . ? C11 N4 C8 C7 -177.9(3) . . . . ? N3 C7 C8 N4 -1.0(5) . . . . ? C6 C7 C8 N4 178.8(3) . . . . ? N3 C7 C8 C9 -178.8(3) . . . . ? C6 C7 C8 C9 1.0(5) . . . . ? N4 C8 C9 F3 179.4(3) . . . . ? C7 C8 C9 F3 -2.4(5) . . . . ? N4 C8 C9 C10 -0.8(4) . . . . ? C7 C8 C9 C10 177.4(3) . . . . ? F3 C9 C10 F4 -0.2(6) . . . . ? C8 C9 C10 F4 180.0(3) . . . . ? F3 C9 C10 C11 -179.2(3) . . . . ? C8 C9 C10 C11 1.0(4) . . . . ? C8 N4 C11 C10 0.3(4) . . . . ? F4 C10 C11 N4 -179.8(3) . . . . ? C9 C10 C11 N4 -0.8(4) . . . . ? O1 C12 C13 F5 -2.3(5) . . . . ? O2 C12 C13 F5 178.9(3) . . . . ? O1 C12 C13 F6 -126.3(4) . . . . ? O2 C12 C13 F6 54.8(4) . . . . ? O1 C12 C13 F7 118.0(4) . . . . ? O2 C12 C13 F7 -60.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 1.207 _refine_diff_density_min -0.578 _refine_diff_density_rms 0.085 #============================================================================== # End of CIF #============================================================================== data_shelxl_3 _database_code_depnum_ccdc_archive 'CCDC 625145' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 N4' _chemical_formula_weight 226.28 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 16.129(5) _cell_length_b 16.450(4) _cell_length_c 36.383(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.023(10) _cell_angle_gamma 90.00 _cell_volume 9653(4) _cell_formula_units_Z 32 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 20254 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3840 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9922 _exptl_absorpt_correction_T_max 0.9961 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45036 _diffrn_reflns_av_R_equivalents 0.1009 _diffrn_reflns_av_sigmaI/netI 0.0905 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 10976 _reflns_number_gt 6337 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.6.0' _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^)+(0.1048P)^2^+19.0511P] 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 10976 _refine_ls_number_parameters 614 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1524 _refine_ls_R_factor_gt 0.0870 _refine_ls_wR_factor_ref 0.2387 _refine_ls_wR_factor_gt 0.2030 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.5568(2) 0.36500(19) 0.02324(8) 0.0419(8) Uani 1 1 d . . . N2 N 0.49001(17) 0.19678(17) 0.08205(7) 0.0301(6) Uani 1 1 d . . . H2N H 0.5104 0.2118 0.1034 0.036 Uiso 1 1 calc R . . N3 N 0.45498(17) 0.12277(17) 0.07563(7) 0.0298(6) Uani 1 1 d . . . N4 N 0.40329(16) 0.03046(16) -0.01204(7) 0.0288(6) Uani 1 1 d . . . N5 N 0.25084(19) -0.0720(2) 0.15283(7) 0.0423(8) Uani 1 1 d . . . N6 N 0.46055(17) 0.00051(17) 0.13435(7) 0.0318(6) Uani 1 1 d . . . H6N H 0.4518 0.0338 0.1158 0.038 Uiso 1 1 calc R . . N7 N 0.53713(17) -0.02143(18) 0.14654(7) 0.0334(7) Uani 1 1 d . . . N8 N 0.5976(2) -0.18371(19) 0.20752(8) 0.0452(8) Uani 1 1 d . . . N9 N 0.76786(19) -0.15610(18) 0.05500(8) 0.0400(7) Uani 1 1 d . . . N10 N 0.68780(17) 0.01298(16) 0.11039(7) 0.0296(6) Uani 1 1 d . . . H10N H 0.6404 -0.0073 0.1181 0.035 Uiso 1 1 calc R . . N11 N 0.71133(17) 0.09075(17) 0.11569(7) 0.0298(6) Uani 1 1 d . . . N12 N 0.80467(18) 0.24657(17) 0.08798(7) 0.0341(7) Uani 1 1 d . . . N13 N 0.68953(18) 0.11952(18) 0.25819(7) 0.0364(7) Uani 1 1 d . . . N14 N 0.61846(17) 0.18113(17) 0.16879(7) 0.0290(6) Uani 1 1 d . . . H14N H 0.6421 0.1429 0.1555 0.035 Uiso 1 1 calc R . . N15 N 0.55929(16) 0.23210(17) 0.15603(7) 0.0304(6) Uani 1 1 d . . . N16 N 0.40551(19) 0.3442(2) 0.16504(8) 0.0472(9) Uani 1 1 d . . . C1 C 0.5707(3) 0.4445(2) 0.03197(10) 0.0497(10) Uani 1 1 d . . . H1 H 0.5961 0.4834 0.0163 0.060 Uiso 1 1 calc R . . C2 C 0.5424(3) 0.4593(2) 0.06646(10) 0.0453(10) Uani 1 1 d . . . H2 H 0.5438 0.5099 0.0790 0.054 Uiso 1 1 calc R . . C3 C 0.5106(2) 0.3858(2) 0.08021(9) 0.0356(8) Uani 1 1 d . . . H3 H 0.4876 0.3775 0.1039 0.043 Uiso 1 1 calc R . . C4 C 0.5188(2) 0.3279(2) 0.05308(8) 0.0305(7) Uani 1 1 d . . . C5 C 0.48982(19) 0.2445(2) 0.05192(8) 0.0277(7) Uani 1 1 d . . . C6 C 0.4529(2) 0.1996(2) 0.02414(8) 0.0291(7) Uani 1 1 d . . . H6 H 0.4440 0.2162 -0.0006 0.035 Uiso 1 1 calc R . . C7 C 0.43164(19) 0.1249(2) 0.03994(8) 0.0272(7) Uani 1 1 d . . . C8 C 0.3892(2) 0.0556(2) 0.02361(8) 0.0269(7) Uani 1 1 d . . . C9 C 0.3342(2) 0.0017(2) 0.03915(9) 0.0333(8) Uani 1 1 d . . . H9 H 0.3131 0.0039 0.0635 0.040 Uiso 1 1 calc R . . C10 C 0.3149(2) -0.0575(2) 0.01225(9) 0.0355(8) Uani 1 1 d . . . H10 H 0.2782 -0.1022 0.0152 0.043 Uiso 1 1 calc R . . C11 C 0.3587(2) -0.0384(2) -0.01862(8) 0.0323(8) Uani 1 1 d . . . H11 H 0.3582 -0.0682 -0.0410 0.039 Uiso 1 1 calc R . . C12 C 0.5805(3) 0.3268(3) -0.01117(11) 0.0689(14) Uani 1 1 d . . . H12A H 0.6371 0.3056 -0.0091 0.083 Uiso 1 1 calc R . . H12C H 0.5781 0.3670 -0.0310 0.083 Uiso 1 1 calc R . . H12B H 0.5424 0.2820 -0.0166 0.083 Uiso 1 1 calc R . . C13 C 0.4561(2) 0.0707(2) -0.03943(8) 0.0310(7) Uani 1 1 d . . . H13A H 0.5124 0.0487 -0.0379 0.037 Uiso 1 1 calc R . . H13B H 0.4574 0.1293 -0.0346 0.037 Uiso 1 1 calc R . . H13C H 0.4336 0.0609 -0.0641 0.037 Uiso 1 1 calc R . . C14 C 0.1782(3) -0.0374(3) 0.14265(10) 0.0538(11) Uani 1 1 d . . . H14 H 0.1253 -0.0627 0.1440 0.065 Uiso 1 1 calc R . . C15 C 0.1929(2) 0.0391(3) 0.13018(11) 0.0542(11) Uani 1 1 d . . . H15 H 0.1525 0.0766 0.1216 0.065 Uiso 1 1 calc R . . C16 C 0.2788(2) 0.0524(2) 0.13224(9) 0.0396(9) Uani 1 1 d . . . H16 H 0.3073 0.1005 0.1251 0.047 Uiso 1 1 calc R . . C17 C 0.3139(2) -0.0167(2) 0.14639(8) 0.0336(8) Uani 1 1 d . . . C18 C 0.3997(2) -0.0349(2) 0.15414(8) 0.0317(8) Uani 1 1 d . . . C19 C 0.4386(2) -0.0822(2) 0.18065(8) 0.0350(8) Uani 1 1 d . . . H19 H 0.4127 -0.1148 0.1989 0.042 Uiso 1 1 calc R . . C20 C 0.5235(2) -0.0720(2) 0.17509(8) 0.0329(8) Uani 1 1 d . . . C21 C 0.5939(2) -0.1046(2) 0.19554(9) 0.0362(8) Uani 1 1 d . . . C22 C 0.6648(2) -0.0667(2) 0.20647(9) 0.0399(9) Uani 1 1 d . . . H22 H 0.6787 -0.0114 0.2022 0.048 Uiso 1 1 calc R . . C23 C 0.7143(3) -0.1245(2) 0.22548(10) 0.0449(9) Uani 1 1 d . . . H23 H 0.7672 -0.1154 0.2362 0.054 Uiso 1 1 calc R . . C24 C 0.6714(3) -0.1948(3) 0.22527(10) 0.0484(10) Uani 1 1 d . . . H24 H 0.6896 -0.2445 0.2358 0.058 Uiso 1 1 calc R . . C25 C 0.2584(3) -0.1535(2) 0.16788(10) 0.0496(11) Uani 1 1 d . . . H25A H 0.2665 -0.1925 0.1478 0.060 Uiso 1 1 calc R . . H25B H 0.2077 -0.1674 0.1814 0.060 Uiso 1 1 calc R . . H25C H 0.3060 -0.1557 0.1846 0.060 Uiso 1 1 calc R . . C26 C 0.5379(4) -0.2479(3) 0.19932(14) 0.0751(16) Uani 1 1 d . . . H26A H 0.5121 -0.2374 0.1754 0.090 Uiso 1 1 calc R . . H26B H 0.4951 -0.2490 0.2184 0.090 Uiso 1 1 calc R . . H26C H 0.5665 -0.3005 0.1986 0.090 Uiso 1 1 calc R . . C27 C 0.7442(3) -0.2359(2) 0.05622(12) 0.0508(10) Uani 1 1 d . . . H27 H 0.7609 -0.2770 0.0394 0.061 Uiso 1 1 calc R . . C28 C 0.6932(3) -0.2467(2) 0.08527(13) 0.0538(11) Uani 1 1 d . . . H28 H 0.6670 -0.2962 0.0921 0.065 Uiso 1 1 calc R . . C29 C 0.6856(2) -0.1711(2) 0.10378(11) 0.0432(9) Uani 1 1 d . . . H29 H 0.6544 -0.1607 0.1254 0.052 Uiso 1 1 calc R . . C30 C 0.7322(2) -0.1159(2) 0.08433(9) 0.0347(8) Uani 1 1 d . . . C31 C 0.7457(2) -0.0305(2) 0.09169(8) 0.0294(7) Uani 1 1 d . . . C32 C 0.8097(2) 0.0230(2) 0.08433(8) 0.0297(7) Uani 1 1 d . . . H32 H 0.8596 0.0115 0.0714 0.036 Uiso 1 1 calc R . . C33 C 0.7865(2) 0.0973(2) 0.09968(8) 0.0274(7) Uani 1 1 d . . . C34 C 0.8343(2) 0.1727(2) 0.09981(8) 0.0295(7) Uani 1 1 d . . . C35 C 0.9171(2) 0.1829(2) 0.10801(9) 0.0363(8) Uani 1 1 d . . . H35 H 0.9538 0.1420 0.1167 0.044 Uiso 1 1 calc R . . C36 C 0.9379(2) 0.2647(2) 0.10115(9) 0.0391(9) Uani 1 1 d . . . H36 H 0.9906 0.2892 0.1046 0.047 Uiso 1 1 calc R . . C37 C 0.8676(2) 0.3020(2) 0.08861(9) 0.0387(9) Uani 1 1 d . . . H37 H 0.8633 0.3574 0.0815 0.046 Uiso 1 1 calc R . . C38 C 0.8156(2) -0.1194(2) 0.02547(10) 0.0433(9) Uani 1 1 d . . . H38A H 0.8567 -0.1585 0.0164 0.052 Uiso 1 1 calc R . . H38B H 0.8441 -0.0708 0.0347 0.052 Uiso 1 1 calc R . . H38C H 0.7784 -0.1040 0.0054 0.052 Uiso 1 1 calc R . . C39 C 0.7206(2) 0.2633(2) 0.07512(11) 0.0450(9) Uani 1 1 d . . . H39A H 0.6816 0.2267 0.0875 0.054 Uiso 1 1 calc R . . H39B H 0.7176 0.2547 0.0485 0.054 Uiso 1 1 calc R . . H39C H 0.7060 0.3198 0.0808 0.054 Uiso 1 1 calc R . . C40 C 0.7607(2) 0.0823(2) 0.26966(9) 0.0415(9) Uani 1 1 d . . . H40 H 0.7685 0.0555 0.2925 0.050 Uiso 1 1 calc R . . C41 C 0.8186(2) 0.0903(2) 0.24261(10) 0.0435(9) Uani 1 1 d . . . H41 H 0.8739 0.0705 0.2433 0.052 Uiso 1 1 calc R . . C42 C 0.7813(2) 0.1336(2) 0.21330(9) 0.0381(8) Uani 1 1 d . . . H42 H 0.8069 0.1480 0.1907 0.046 Uiso 1 1 calc R . . C43 C 0.7017(2) 0.1507(2) 0.22354(8) 0.0309(7) Uani 1 1 d . . . C44 C 0.6370(2) 0.19599(19) 0.20454(8) 0.0273(7) Uani 1 1 d . . . C45 C 0.58644(19) 0.2584(2) 0.21575(8) 0.0283(7) Uani 1 1 d . . . H45 H 0.5841 0.2823 0.2395 0.034 Uiso 1 1 calc R . . C46 C 0.5390(2) 0.2794(2) 0.18493(8) 0.0302(7) Uani 1 1 d . . . C47 C 0.4816(2) 0.3479(2) 0.18203(9) 0.0363(8) Uani 1 1 d . . . C48 C 0.4959(3) 0.4266(3) 0.19241(10) 0.0503(10) Uani 1 1 d . . . H48 H 0.5434 0.4464 0.2050 0.060 Uiso 1 1 calc R . . C49 C 0.4268(3) 0.4731(3) 0.18082(11) 0.0602(13) Uani 1 1 d . . . H49 H 0.4197 0.5301 0.1837 0.072 Uiso 1 1 calc R . . C50 C 0.3722(3) 0.4205(3) 0.16474(11) 0.0616(14) Uani 1 1 d . . . H50 H 0.3195 0.4347 0.1549 0.074 Uiso 1 1 calc R . . C51 C 0.6091(3) 0.1103(3) 0.27631(11) 0.0595(12) Uani 1 1 d . . . H51A H 0.5659 0.1020 0.2577 0.071 Uiso 1 1 calc R . . H51B H 0.5967 0.1595 0.2905 0.071 Uiso 1 1 calc R . . H51C H 0.6108 0.0633 0.2928 0.071 Uiso 1 1 calc R . . C52 C 0.3630(3) 0.2721(3) 0.15267(13) 0.0681(14) Uani 1 1 d . . . H52A H 0.3779 0.2262 0.1685 0.082 Uiso 1 1 calc R . . H52B H 0.3792 0.2601 0.1273 0.082 Uiso 1 1 calc R . . H52C H 0.3030 0.2811 0.1538 0.082 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 0.057(2) 0.0380(18) 0.0310(15) 0.0024(12) -0.0003(14) -0.0149(15) N2 0.0342(15) 0.0325(16) 0.0235(12) 0.0005(11) -0.0068(11) -0.0063(13) N3 0.0326(15) 0.0313(16) 0.0254(13) 0.0013(11) -0.0064(11) -0.0039(12) N4 0.0297(15) 0.0304(16) 0.0263(13) 0.0030(11) -0.0095(11) -0.0003(12) N5 0.0421(18) 0.053(2) 0.0320(15) 0.0053(13) -0.0060(13) -0.0220(16) N6 0.0357(16) 0.0327(16) 0.0271(13) 0.0067(11) -0.0015(12) -0.0070(13) N7 0.0351(16) 0.0355(17) 0.0297(14) 0.0056(12) -0.0048(12) -0.0028(13) N8 0.060(2) 0.0348(18) 0.0411(16) 0.0087(13) -0.0132(15) -0.0101(16) N9 0.0402(17) 0.0292(17) 0.0507(18) -0.0061(13) -0.0140(14) 0.0020(14) N10 0.0308(15) 0.0285(16) 0.0294(13) 0.0035(11) -0.0042(11) -0.0018(12) N11 0.0336(15) 0.0293(16) 0.0265(13) -0.0008(11) -0.0011(11) -0.0056(13) N12 0.0401(17) 0.0303(16) 0.0319(14) 0.0017(12) 0.0000(12) -0.0034(14) N13 0.0412(17) 0.0407(18) 0.0272(14) 0.0051(12) -0.0036(12) 0.0068(14) N14 0.0322(15) 0.0308(16) 0.0240(13) -0.0011(11) -0.0027(11) -0.0013(12) N15 0.0278(15) 0.0365(17) 0.0267(13) 0.0012(11) -0.0044(11) -0.0010(13) N16 0.0318(17) 0.076(3) 0.0334(16) 0.0090(15) -0.0031(13) 0.0096(17) C1 0.061(3) 0.042(2) 0.046(2) 0.0095(17) -0.0130(19) -0.020(2) C2 0.060(3) 0.034(2) 0.042(2) -0.0028(16) -0.0145(18) -0.0108(19) C3 0.045(2) 0.033(2) 0.0294(16) -0.0019(14) -0.0059(15) -0.0061(16) C4 0.0358(18) 0.0325(19) 0.0232(15) 0.0043(13) -0.0050(13) -0.0045(15) C5 0.0272(17) 0.0322(19) 0.0235(15) 0.0019(12) -0.0028(13) 0.0000(14) C6 0.0342(18) 0.0308(18) 0.0222(15) 0.0028(12) -0.0042(13) 0.0011(15) C7 0.0267(16) 0.0318(18) 0.0231(14) 0.0014(12) -0.0045(12) 0.0015(14) C8 0.0279(16) 0.0300(18) 0.0227(14) 0.0036(12) -0.0064(12) 0.0026(14) C9 0.0308(18) 0.040(2) 0.0295(16) 0.0028(14) -0.0052(14) -0.0044(16) C10 0.0355(19) 0.035(2) 0.0359(18) 0.0045(14) -0.0117(15) -0.0072(16) C11 0.040(2) 0.0289(19) 0.0282(16) 0.0001(13) -0.0122(14) -0.0028(15) C12 0.099(4) 0.072(3) 0.037(2) -0.008(2) 0.023(2) -0.028(3) C13 0.0349(19) 0.0308(19) 0.0275(15) 0.0024(13) -0.0059(14) 0.0016(15) C14 0.041(2) 0.076(3) 0.045(2) 0.014(2) -0.0095(18) -0.024(2) C15 0.036(2) 0.076(3) 0.051(2) 0.016(2) -0.0145(18) -0.012(2) C16 0.039(2) 0.049(2) 0.0299(17) 0.0035(15) -0.0067(15) -0.0128(18) C17 0.039(2) 0.040(2) 0.0217(15) -0.0002(13) -0.0016(14) -0.0173(16) C18 0.0376(19) 0.0338(19) 0.0236(15) -0.0024(13) 0.0015(14) -0.0120(16) C19 0.044(2) 0.034(2) 0.0263(16) 0.0040(13) -0.0018(15) -0.0126(16) C20 0.043(2) 0.0272(18) 0.0284(16) 0.0017(13) -0.0037(15) -0.0049(16) C21 0.046(2) 0.032(2) 0.0302(17) 0.0039(14) -0.0017(15) -0.0036(17) C22 0.046(2) 0.036(2) 0.0378(18) 0.0025(15) -0.0048(16) -0.0033(18) C23 0.052(2) 0.047(2) 0.0360(19) 0.0049(16) -0.0077(17) -0.001(2) C24 0.062(3) 0.045(2) 0.039(2) 0.0090(16) -0.0143(19) 0.007(2) C25 0.058(3) 0.053(3) 0.0379(19) 0.0056(17) -0.0044(18) -0.032(2) C26 0.098(4) 0.042(3) 0.086(3) 0.021(2) -0.040(3) -0.023(3) C27 0.052(3) 0.030(2) 0.070(3) -0.0098(19) -0.020(2) 0.0013(19) C28 0.053(3) 0.030(2) 0.079(3) 0.005(2) -0.022(2) -0.0103(19) C29 0.037(2) 0.036(2) 0.056(2) 0.0074(17) -0.0134(17) -0.0015(17) C30 0.0304(18) 0.030(2) 0.0435(19) 0.0000(15) -0.0132(15) 0.0028(15) C31 0.0315(18) 0.0319(19) 0.0250(15) 0.0008(13) -0.0089(13) 0.0034(15) C32 0.0279(17) 0.0298(19) 0.0314(16) -0.0031(13) -0.0082(13) -0.0006(14) C33 0.0309(17) 0.0284(18) 0.0229(14) 0.0017(12) -0.0066(13) -0.0020(14) C34 0.0347(18) 0.0304(19) 0.0233(15) -0.0017(13) -0.0013(13) -0.0034(15) C35 0.037(2) 0.039(2) 0.0324(17) -0.0001(14) -0.0051(15) -0.0041(17) C36 0.044(2) 0.041(2) 0.0319(17) -0.0041(15) -0.0017(16) -0.0136(18) C37 0.049(2) 0.033(2) 0.0337(18) -0.0009(14) 0.0008(16) -0.0135(18) C38 0.048(2) 0.041(2) 0.041(2) -0.0081(16) -0.0066(17) 0.0037(18) C39 0.042(2) 0.042(2) 0.052(2) 0.0118(17) -0.0066(18) 0.0006(18) C40 0.054(2) 0.042(2) 0.0286(17) -0.0010(15) -0.0092(17) 0.0134(19) C41 0.045(2) 0.044(2) 0.042(2) -0.0057(16) -0.0117(17) 0.0169(18) C42 0.044(2) 0.039(2) 0.0314(17) -0.0038(15) -0.0040(15) 0.0097(17) C43 0.0372(19) 0.0298(19) 0.0257(15) -0.0032(13) -0.0059(14) 0.0002(15) C44 0.0303(17) 0.0269(18) 0.0248(15) 0.0021(12) -0.0018(13) -0.0027(14) C45 0.0271(17) 0.0315(19) 0.0263(15) 0.0012(13) -0.0005(13) -0.0010(14) C46 0.0251(17) 0.040(2) 0.0253(15) 0.0003(13) 0.0006(13) -0.0029(15) C47 0.0291(18) 0.054(2) 0.0260(16) 0.0033(15) -0.0003(14) 0.0095(17) C48 0.051(2) 0.054(3) 0.045(2) -0.0055(19) 0.0007(18) 0.025(2) C49 0.072(3) 0.063(3) 0.045(2) 0.003(2) 0.007(2) 0.033(3) C50 0.049(3) 0.099(4) 0.037(2) 0.014(2) 0.0046(19) 0.036(3) C51 0.055(3) 0.082(3) 0.041(2) 0.025(2) 0.0086(19) 0.016(2) C52 0.037(2) 0.101(4) 0.066(3) -0.001(3) -0.012(2) 0.000(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 N1 C1 1.364(5) . ? N1 C4 1.388(4) . ? N1 C12 1.452(5) . ? N2 C5 1.348(4) . ? N2 N3 1.362(4) . ? N2 H2N 0.8800 . ? N3 C7 1.352(4) . ? N4 C11 1.363(4) . ? N4 C8 1.380(4) . ? N4 C13 1.468(4) . ? N5 C14 1.355(5) . ? N5 C17 1.385(4) . ? N5 C25 1.453(5) . ? N6 C18 1.350(4) . ? N6 N7 1.361(4) . ? N6 H6N 0.8800 . ? N7 C20 1.349(4) . ? N8 C24 1.366(5) . ? N8 C21 1.373(5) . ? N8 C26 1.460(5) . ? N9 C27 1.368(5) . ? N9 C30 1.381(5) . ? N9 C38 1.454(5) . ? N10 N11 1.348(4) . ? N10 C31 1.358(4) . ? N10 H10N 0.8800 . ? N11 C33 1.350(4) . ? N12 C37 1.365(4) . ? N12 C34 1.374(4) . ? N12 C39 1.461(5) . ? N13 C40 1.366(5) . ? N13 C43 1.375(4) . ? N13 C51 1.464(5) . ? N14 N15 1.353(4) . ? N14 C44 1.357(4) . ? N14 H14N 0.8800 . ? N15 C46 1.349(4) . ? N16 C50 1.365(6) . ? N16 C47 1.375(4) . ? N16 C52 1.442(6) . ? C1 C2 1.357(5) . ? C1 H1 0.9500 . ? C2 C3 1.404(5) . ? C2 H2 0.9500 . ? C3 C4 1.379(5) . ? C3 H3 0.9500 . ? C4 C5 1.450(5) . ? C5 C6 1.385(4) . ? C6 C7 1.400(4) . ? C6 H6 0.9500 . ? C7 C8 1.456(4) . ? C8 C9 1.375(5) . ? C9 C10 1.416(5) . ? C9 H9 0.9500 . ? C10 C11 1.364(5) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12C 0.9800 . ? C12 H12B 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.358(6) . ? C14 H14 0.9500 . ? C15 C16 1.405(5) . ? C15 H15 0.9500 . ? C16 C17 1.370(5) . ? C16 H16 0.9500 . ? C17 C18 1.444(5) . ? C18 C19 1.389(5) . ? C19 C20 1.394(5) . ? C19 H19 0.9500 . ? C20 C21 1.459(5) . ? C21 C22 1.362(5) . ? C22 C23 1.421(5) . ? C22 H22 0.9500 . ? C23 C24 1.348(6) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.351(6) . ? C27 H27 0.9500 . ? C28 C29 1.419(6) . ? C28 H28 0.9500 . ? C29 C30 1.376(5) . ? C29 H29 0.9500 . ? C30 C31 1.446(5) . ? C31 C32 1.384(5) . ? C32 C33 1.395(4) . ? C32 H32 0.9500 . ? C33 C34 1.461(5) . ? C34 C35 1.380(5) . ? C35 C36 1.408(5) . ? C35 H35 0.9500 . ? C36 C37 1.367(5) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 C41 1.363(5) . ? C40 H40 0.9500 . ? C41 C42 1.415(5) . ? C41 H41 0.9500 . ? C42 C43 1.367(5) . ? C42 H42 0.9500 . ? C43 C44 1.456(5) . ? C44 C45 1.373(4) . ? C45 C46 1.401(4) . ? C45 H45 0.9500 . ? C46 C47 1.463(5) . ? C47 C48 1.368(6) . ? C48 C49 1.416(6) . ? C48 H48 0.9500 . ? C49 C50 1.367(7) . ? C49 H49 0.9500 . ? C50 H50 0.9500 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? 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 C1 N1 C4 108.2(3) . . ? C1 N1 C12 124.9(3) . . ? C4 N1 C12 126.9(3) . . ? C5 N2 N3 112.3(2) . . ? C5 N2 H2N 123.8 . . ? N3 N2 H2N 123.8 . . ? C7 N3 N2 104.9(2) . . ? C11 N4 C8 109.1(3) . . ? C11 N4 C13 124.1(3) . . ? C8 N4 C13 126.8(3) . . ? C14 N5 C17 108.2(3) . . ? C14 N5 C25 124.3(3) . . ? C17 N5 C25 127.5(3) . . ? C18 N6 N7 111.9(3) . . ? C18 N6 H6N 124.1 . . ? N7 N6 H6N 124.1 . . ? C20 N7 N6 105.4(3) . . ? C24 N8 C21 108.4(3) . . ? C24 N8 C26 125.0(4) . . ? C21 N8 C26 126.3(3) . . ? C27 N9 C30 108.6(3) . . ? C27 N9 C38 124.8(3) . . ? C30 N9 C38 126.3(3) . . ? N11 N10 C31 112.2(3) . . ? N11 N10 H10N 123.9 . . ? C31 N10 H10N 123.9 . . ? N10 N11 C33 105.5(3) . . ? C37 N12 C34 109.1(3) . . ? C37 N12 C39 124.7(3) . . ? C34 N12 C39 126.1(3) . . ? C40 N13 C43 109.1(3) . . ? C40 N13 C51 124.2(3) . . ? C43 N13 C51 125.3(3) . . ? N15 N14 C44 111.9(3) . . ? N15 N14 H14N 124.0 . . ? C44 N14 H14N 124.0 . . ? C46 N15 N14 105.2(2) . . ? C50 N16 C47 108.3(4) . . ? C50 N16 C52 124.5(4) . . ? C47 N16 C52 126.9(4) . . ? C2 C1 N1 109.4(3) . . ? C2 C1 H1 125.3 . . ? N1 C1 H1 125.3 . . ? C1 C2 C3 107.3(3) . . ? C1 C2 H2 126.3 . . ? C3 C2 H2 126.3 . . ? C4 C3 C2 107.7(3) . . ? C4 C3 H3 126.1 . . ? C2 C3 H3 126.1 . . ? C3 C4 N1 107.4(3) . . ? C3 C4 C5 130.1(3) . . ? N1 C4 C5 122.4(3) . . ? N2 C5 C6 106.5(3) . . ? N2 C5 C4 121.8(3) . . ? C6 C5 C4 131.6(3) . . ? C5 C6 C7 105.9(3) . . ? C5 C6 H6 127.1 . . ? C7 C6 H6 127.1 . . ? N3 C7 C6 110.4(3) . . ? N3 C7 C8 120.2(3) . . ? C6 C7 C8 129.4(3) . . ? C9 C8 N4 107.5(3) . . ? C9 C8 C7 129.8(3) . . ? N4 C8 C7 122.7(3) . . ? C8 C9 C10 107.5(3) . . ? C8 C9 H9 126.2 . . ? C10 C9 H9 126.2 . . ? C11 C10 C9 107.3(3) . . ? C11 C10 H10 126.4 . . ? C9 C10 H10 126.4 . . ? N4 C11 C10 108.6(3) . . ? N4 C11 H11 125.7 . . ? C10 C11 H11 125.7 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? N4 C13 H13A 109.5 . . ? N4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N5 C14 C15 109.2(4) . . ? N5 C14 H14 125.4 . . ? C15 C14 H14 125.4 . . ? C14 C15 C16 107.4(4) . . ? C14 C15 H15 126.3 . . ? C16 C15 H15 126.3 . . ? C17 C16 C15 107.3(3) . . ? C17 C16 H16 126.4 . . ? C15 C16 H16 126.4 . . ? C16 C17 N5 107.8(3) . . ? C16 C17 C18 129.9(3) . . ? N5 C17 C18 122.3(3) . . ? N6 C18 C19 106.4(3) . . ? N6 C18 C17 120.2(3) . . ? C19 C18 C17 133.3(3) . . ? C18 C19 C20 106.0(3) . . ? C18 C19 H19 127.0 . . ? C20 C19 H19 127.0 . . ? N7 C20 C19 110.2(3) . . ? N7 C20 C21 119.5(3) . . ? C19 C20 C21 130.2(3) . . ? C22 C21 N8 107.7(3) . . ? C22 C21 C20 129.3(3) . . ? N8 C21 C20 123.0(3) . . ? C21 C22 C23 107.9(3) . . ? C21 C22 H22 126.0 . . ? C23 C22 H22 126.0 . . ? C24 C23 C22 106.4(4) . . ? C24 C23 H23 126.8 . . ? C22 C23 H23 126.8 . . ? C23 C24 N8 109.6(4) . . ? C23 C24 H24 125.2 . . ? N8 C24 H24 125.2 . . ? N5 C25 H25A 109.5 . . ? N5 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N5 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N8 C26 H26A 109.5 . . ? N8 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N8 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 N9 108.7(4) . . ? C28 C27 H27 125.6 . . ? N9 C27 H27 125.6 . . ? C27 C28 C29 108.0(4) . . ? C27 C28 H28 126.0 . . ? C29 C28 H28 126.0 . . ? C30 C29 C28 106.7(4) . . ? C30 C29 H29 126.7 . . ? C28 C29 H29 126.7 . . ? C29 C30 N9 108.0(3) . . ? C29 C30 C31 128.9(3) . . ? N9 C30 C31 123.1(3) . . ? N10 C31 C32 106.0(3) . . ? N10 C31 C30 120.1(3) . . ? C32 C31 C30 133.9(3) . . ? C31 C32 C33 106.2(3) . . ? C31 C32 H32 126.9 . . ? C33 C32 H32 126.9 . . ? N11 C33 C32 110.2(3) . . ? N11 C33 C34 122.7(3) . . ? C32 C33 C34 127.1(3) . . ? N12 C34 C35 107.3(3) . . ? N12 C34 C33 124.5(3) . . ? C35 C34 C33 128.0(3) . . ? C34 C35 C36 107.9(3) . . ? C34 C35 H35 126.0 . . ? C36 C35 H35 126.0 . . ? C37 C36 C35 107.0(3) . . ? C37 C36 H36 126.5 . . ? C35 C36 H36 126.5 . . ? N12 C37 C36 108.7(3) . . ? N12 C37 H37 125.6 . . ? C36 C37 H37 125.6 . . ? N9 C38 H38A 109.5 . . ? N9 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? N9 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N12 C39 H39A 109.5 . . ? N12 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? N12 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C41 C40 N13 108.2(3) . . ? C41 C40 H40 125.9 . . ? N13 C40 H40 125.9 . . ? C40 C41 C42 107.6(3) . . ? C40 C41 H41 126.2 . . ? C42 C41 H41 126.2 . . ? C43 C42 C41 107.3(3) . . ? C43 C42 H42 126.4 . . ? C41 C42 H42 126.4 . . ? C42 C43 N13 107.9(3) . . ? C42 C43 C44 130.5(3) . . ? N13 C43 C44 121.6(3) . . ? N14 C44 C45 106.8(3) . . ? N14 C44 C43 121.4(3) . . ? C45 C44 C43 131.8(3) . . ? C44 C45 C46 105.8(3) . . ? C44 C45 H45 127.1 . . ? C46 C45 H45 127.1 . . ? N15 C46 C45 110.4(3) . . ? N15 C46 C47 122.8(3) . . ? C45 C46 C47 126.4(3) . . ? C48 C47 N16 108.5(3) . . ? C48 C47 C46 127.1(3) . . ? N16 C47 C46 124.3(4) . . ? C47 C48 C49 107.2(4) . . ? C47 C48 H48 126.4 . . ? C49 C48 H48 126.4 . . ? C50 C49 C48 107.0(4) . . ? C50 C49 H49 126.5 . . ? C48 C49 H49 126.5 . . ? N16 C50 C49 108.9(4) . . ? N16 C50 H50 125.5 . . ? C49 C50 H50 125.5 . . ? N13 C51 H51A 109.5 . . ? N13 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? N13 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? N16 C52 H52A 109.5 . . ? N16 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? N16 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N2 N3 C7 -0.3(3) . . . . ? C18 N6 N7 C20 -0.3(4) . . . . ? C31 N10 N11 C33 0.3(3) . . . . ? C44 N14 N15 C46 -1.2(3) . . . . ? C4 N1 C1 C2 -0.2(5) . . . . ? C12 N1 C1 C2 -178.6(4) . . . . ? N1 C1 C2 C3 0.9(5) . . . . ? C1 C2 C3 C4 -1.3(4) . . . . ? C2 C3 C4 N1 1.2(4) . . . . ? C2 C3 C4 C5 -174.3(3) . . . . ? C1 N1 C4 C3 -0.6(4) . . . . ? C12 N1 C4 C3 177.7(4) . . . . ? C1 N1 C4 C5 175.3(3) . . . . ? C12 N1 C4 C5 -6.4(6) . . . . ? N3 N2 C5 C6 -0.1(4) . . . . ? N3 N2 C5 C4 175.7(3) . . . . ? C3 C4 C5 N2 -37.1(5) . . . . ? N1 C4 C5 N2 148.0(3) . . . . ? C3 C4 C5 C6 137.5(4) . . . . ? N1 C4 C5 C6 -37.3(6) . . . . ? N2 C5 C6 C7 0.5(4) . . . . ? C4 C5 C6 C7 -174.7(3) . . . . ? N2 N3 C7 C6 0.6(3) . . . . ? N2 N3 C7 C8 -178.3(3) . . . . ? C5 C6 C7 N3 -0.7(4) . . . . ? C5 C6 C7 C8 178.1(3) . . . . ? C11 N4 C8 C9 -0.7(4) . . . . ? C13 N4 C8 C9 178.3(3) . . . . ? C11 N4 C8 C7 176.3(3) . . . . ? C13 N4 C8 C7 -4.8(5) . . . . ? N3 C7 C8 C9 33.7(5) . . . . ? C6 C7 C8 C9 -145.0(4) . . . . ? N3 C7 C8 N4 -142.5(3) . . . . ? C6 C7 C8 N4 38.8(5) . . . . ? N4 C8 C9 C10 0.2(4) . . . . ? C7 C8 C9 C10 -176.5(3) . . . . ? C8 C9 C10 C11 0.3(4) . . . . ? C8 N4 C11 C10 0.9(4) . . . . ? C13 N4 C11 C10 -178.1(3) . . . . ? C9 C10 C11 N4 -0.8(4) . . . . ? C17 N5 C14 C15 -0.6(4) . . . . ? C25 N5 C14 C15 179.3(3) . . . . ? N5 C14 C15 C16 0.8(5) . . . . ? C14 C15 C16 C17 -0.6(4) . . . . ? C15 C16 C17 N5 0.3(4) . . . . ? C15 C16 C17 C18 -179.9(3) . . . . ? C14 N5 C17 C16 0.2(4) . . . . ? C25 N5 C17 C16 -179.7(3) . . . . ? C14 N5 C17 C18 -179.7(3) . . . . ? C25 N5 C17 C18 0.5(5) . . . . ? N7 N6 C18 C19 0.2(4) . . . . ? N7 N6 C18 C17 177.5(3) . . . . ? C16 C17 C18 N6 -28.8(5) . . . . ? N5 C17 C18 N6 151.0(3) . . . . ? C16 C17 C18 C19 147.8(4) . . . . ? N5 C17 C18 C19 -32.4(6) . . . . ? N6 C18 C19 C20 0.1(4) . . . . ? C17 C18 C19 C20 -176.8(4) . . . . ? N6 N7 C20 C19 0.4(4) . . . . ? N6 N7 C20 C21 -177.7(3) . . . . ? C18 C19 C20 N7 -0.3(4) . . . . ? C18 C19 C20 C21 177.5(3) . . . . ? C24 N8 C21 C22 -1.0(4) . . . . ? C26 N8 C21 C22 -174.6(4) . . . . ? C24 N8 C21 C20 179.4(3) . . . . ? C26 N8 C21 C20 5.8(6) . . . . ? N7 C20 C21 C22 41.2(5) . . . . ? C19 C20 C21 C22 -136.4(4) . . . . ? N7 C20 C21 N8 -139.3(3) . . . . ? C19 C20 C21 N8 43.0(6) . . . . ? N8 C21 C22 C23 0.6(4) . . . . ? C20 C21 C22 C23 -179.8(3) . . . . ? C21 C22 C23 C24 0.0(4) . . . . ? C22 C23 C24 N8 -0.6(4) . . . . ? C21 N8 C24 C23 1.0(4) . . . . ? C26 N8 C24 C23 174.7(4) . . . . ? C30 N9 C27 C28 1.1(4) . . . . ? C38 N9 C27 C28 -173.2(3) . . . . ? N9 C27 C28 C29 -1.4(5) . . . . ? C27 C28 C29 C30 1.1(4) . . . . ? C28 C29 C30 N9 -0.4(4) . . . . ? C28 C29 C30 C31 -179.6(3) . . . . ? C27 N9 C30 C29 -0.4(4) . . . . ? C38 N9 C30 C29 173.8(3) . . . . ? C27 N9 C30 C31 178.8(3) . . . . ? C38 N9 C30 C31 -6.9(5) . . . . ? N11 N10 C31 C32 -0.5(3) . . . . ? N11 N10 C31 C30 178.3(3) . . . . ? C29 C30 C31 N10 -26.9(5) . . . . ? N9 C30 C31 N10 154.0(3) . . . . ? C29 C30 C31 C32 151.5(4) . . . . ? N9 C30 C31 C32 -27.6(6) . . . . ? N10 C31 C32 C33 0.5(3) . . . . ? C30 C31 C32 C33 -178.0(3) . . . . ? N10 N11 C33 C32 0.0(3) . . . . ? N10 N11 C33 C34 -179.1(3) . . . . ? C31 C32 C33 N11 -0.3(3) . . . . ? C31 C32 C33 C34 178.7(3) . . . . ? C37 N12 C34 C35 0.2(3) . . . . ? C39 N12 C34 C35 177.6(3) . . . . ? C37 N12 C34 C33 -174.3(3) . . . . ? C39 N12 C34 C33 3.2(5) . . . . ? N11 C33 C34 N12 -53.5(4) . . . . ? C32 C33 C34 N12 127.6(4) . . . . ? N11 C33 C34 C35 133.2(4) . . . . ? C32 C33 C34 C35 -45.7(5) . . . . ? N12 C34 C35 C36 0.3(4) . . . . ? C33 C34 C35 C36 174.5(3) . . . . ? C34 C35 C36 C37 -0.6(4) . . . . ? C34 N12 C37 C36 -0.6(4) . . . . ? C39 N12 C37 C36 -178.1(3) . . . . ? C35 C36 C37 N12 0.7(4) . . . . ? C43 N13 C40 C41 0.6(4) . . . . ? C51 N13 C40 C41 167.5(4) . . . . ? N13 C40 C41 C42 -0.4(4) . . . . ? C40 C41 C42 C43 0.1(4) . . . . ? C41 C42 C43 N13 0.2(4) . . . . ? C41 C42 C43 C44 177.7(3) . . . . ? C40 N13 C43 C42 -0.5(4) . . . . ? C51 N13 C43 C42 -167.2(4) . . . . ? C40 N13 C43 C44 -178.2(3) . . . . ? C51 N13 C43 C44 15.0(5) . . . . ? N15 N14 C44 C45 1.3(4) . . . . ? N15 N14 C44 C43 -177.3(3) . . . . ? C42 C43 C44 N14 48.6(5) . . . . ? N13 C43 C44 N14 -134.2(3) . . . . ? C42 C43 C44 C45 -129.6(4) . . . . ? N13 C43 C44 C45 47.6(5) . . . . ? N14 C44 C45 C46 -0.8(3) . . . . ? C43 C44 C45 C46 177.6(3) . . . . ? N14 N15 C46 C45 0.7(4) . . . . ? N14 N15 C46 C47 174.7(3) . . . . ? C44 C45 C46 N15 0.1(4) . . . . ? C44 C45 C46 C47 -173.6(3) . . . . ? C50 N16 C47 C48 0.0(4) . . . . ? C52 N16 C47 C48 -174.3(4) . . . . ? C50 N16 C47 C46 -174.9(3) . . . . ? C52 N16 C47 C46 10.8(5) . . . . ? N15 C46 C47 C48 -125.9(4) . . . . ? C45 C46 C47 C48 47.1(5) . . . . ? N15 C46 C47 N16 48.0(5) . . . . ? C45 C46 C47 N16 -139.0(3) . . . . ? N16 C47 C48 C49 -1.0(4) . . . . ? C46 C47 C48 C49 173.7(3) . . . . ? C47 C48 C49 C50 1.6(4) . . . . ? C47 N16 C50 C49 1.0(4) . . . . ? C52 N16 C50 C49 175.5(4) . . . . ? C48 C49 C50 N16 -1.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.536 _refine_diff_density_min -0.563 _refine_diff_density_rms 0.067 #============================================================================== # End of CIF #==============================================================================