# Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Raju Mondal' _publ_contact_author_email ICRM@IACS.RES.IN _publ_section_title ; Construction of First Anion-Assisted Helix inside a Helix Network ; loop_ _publ_author_name 'Raju Mondal' 'Tannistha Basu' # Attachment 'CLO4.cif' data_rm7 _database_code_depnum_ccdc_archive 'CCDC 742408' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 Cl2 N4 O8' _chemical_formula_weight 405.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.7440(3) _cell_length_b 13.7417(3) _cell_length_c 16.8120(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3406.24(13) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9718 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.68 _exptl_crystal_description Cube _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.580 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.430 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.857938 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0706 before correction' _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 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 47448 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 30.62 _reflns_number_total 5200 _reflns_number_gt 3863 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0764P)^2^+2.6376P] 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 5200 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1478 _refine_ls_wR_factor_gt 0.1342 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 Cl2 Cl 0.23504(3) 0.46850(4) 0.14983(3) 0.02630(14) Uani 1 1 d . . . N1 N 0.46187(12) 0.56247(12) 0.10793(10) 0.0218(3) Uani 1 1 d . . . C2 C 0.57723(12) 0.65458(13) 0.14448(10) 0.0170(3) Uani 1 1 d . . . C3 C 0.60998(13) 0.56471(14) 0.11950(11) 0.0198(4) Uani 1 1 d . . . N3 N 0.57714(14) 0.97412(15) 0.08183(15) 0.0357(5) Uani 1 1 d . . . C8 C 0.41156(13) 0.72341(15) 0.15408(12) 0.0233(4) Uani 1 1 d . . . H8A H 0.3531 0.6967 0.1416 0.035 Uiso 1 1 calc R . . H8B H 0.4218 0.7806 0.1225 0.035 Uiso 1 1 calc R . . H8C H 0.4137 0.7403 0.2095 0.035 Uiso 1 1 calc R . . C4 C 0.57689(14) 0.91541(15) 0.14559(13) 0.0265(4) Uani 1 1 d . . . N2 N 0.53853(12) 0.51083(13) 0.09724(10) 0.0238(4) Uani 1 1 d . . . C7 C 0.63145(13) 0.73972(14) 0.17331(12) 0.0198(4) Uani 1 1 d . . . C5 C 0.61778(12) 0.82834(13) 0.12275(12) 0.0196(4) Uani 1 1 d . . . O5 O 0.14406(11) 0.46853(13) 0.11801(11) 0.0388(4) Uani 1 1 d . . . C9 C 0.70428(15) 0.52668(16) 0.11436(14) 0.0288(4) Uani 1 1 d . . . H9A H 0.7032 0.4612 0.0944 0.043 Uiso 1 1 calc R . . H9B H 0.7314 0.5274 0.1663 0.043 Uiso 1 1 calc R . . H9C H 0.7391 0.5669 0.0791 0.043 Uiso 1 1 calc R . . C6 C 0.64268(13) 0.84025(15) 0.04329(12) 0.0247(4) Uani 1 1 d . . . C1 C 0.48281(12) 0.65035(14) 0.13655(11) 0.0182(4) Uani 1 1 d . . . O6 O 0.29733(12) 0.47038(15) 0.08329(11) 0.0448(5) Uani 1 1 d . . . N4 N 0.61717(13) 0.92929(15) 0.02085(13) 0.0338(5) Uani 1 1 d . . . C11 C 0.69015(15) 0.7733(2) -0.01217(13) 0.0343(5) Uani 1 1 d . . . H11A H 0.6968 0.8042 -0.0630 0.051 Uiso 1 1 calc R . . H11B H 0.6554 0.7147 -0.0181 0.051 Uiso 1 1 calc R . . H11C H 0.7489 0.7577 0.0088 0.051 Uiso 1 1 calc R . . O7 O 0.24934(16) 0.55447(15) 0.19545(12) 0.0541(6) Uani 1 1 d . . . O8 O 0.24743(14) 0.38461(15) 0.19700(14) 0.0582(6) Uani 1 1 d . . . C10 C 0.53856(18) 0.94633(19) 0.22330(16) 0.0414(6) Uani 1 1 d . . . H10A H 0.5153 1.0114 0.2188 0.062 Uiso 1 1 calc R . . H10B H 0.5852 0.9446 0.2631 0.062 Uiso 1 1 calc R . . H10C H 0.4904 0.9030 0.2382 0.062 Uiso 1 1 calc R . . Cl1 Cl 0.05761(3) 0.24081(3) 0.40529(3) 0.02306(13) Uani 1 1 d . . . O1 O 0.01124(14) 0.31780(12) 0.44753(12) 0.0427(5) Uani 1 1 d . . . O2 O 0.13180(13) 0.28053(15) 0.36263(12) 0.0458(5) Uani 1 1 d . . . O3 O -0.00414(15) 0.19211(17) 0.35333(12) 0.0545(6) Uani 1 1 d . . . O4 O 0.08795(16) 0.17156(13) 0.46363(12) 0.0495(5) Uani 1 1 d . . . H7A H 0.6174(19) 0.7516(19) 0.2271(17) 0.035(7) Uiso 1 1 d . . . H7B H 0.6967(18) 0.7232(18) 0.1726(15) 0.027(6) Uiso 1 1 d . . . H222 H 0.5372(19) 0.454(2) 0.0866(16) 0.031(7) Uiso 1 1 d . . . H111 H 0.4112(18) 0.5358(18) 0.0981(15) 0.027(7) Uiso 1 1 d . . . H444 H 0.626(2) 0.960(2) -0.020(2) 0.058(10) Uiso 1 1 d . . . H333 H 0.567(2) 1.024(2) 0.075(2) 0.046(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl2 0.0246(2) 0.0267(3) 0.0275(2) 0.00567(18) -0.00363(18) -0.00793(18) N1 0.0210(8) 0.0175(8) 0.0270(8) 0.0012(6) 0.0001(6) -0.0033(6) C2 0.0175(8) 0.0156(8) 0.0180(8) 0.0028(6) 0.0010(6) 0.0001(6) C3 0.0222(9) 0.0178(9) 0.0195(8) 0.0028(7) 0.0029(7) 0.0027(7) N3 0.0289(10) 0.0155(9) 0.0626(14) 0.0089(9) -0.0180(9) -0.0043(7) C8 0.0181(8) 0.0207(9) 0.0311(10) 0.0004(8) 0.0010(7) 0.0027(7) C4 0.0224(9) 0.0179(9) 0.0391(11) -0.0054(8) -0.0105(8) -0.0005(7) N2 0.0282(9) 0.0133(8) 0.0300(9) -0.0020(7) 0.0031(7) -0.0009(6) C7 0.0203(9) 0.0179(9) 0.0213(9) -0.0009(7) -0.0026(7) -0.0011(7) C5 0.0172(8) 0.0155(9) 0.0260(9) -0.0010(7) -0.0038(7) -0.0030(6) O5 0.0219(8) 0.0500(11) 0.0446(9) 0.0220(8) -0.0030(7) -0.0062(7) C9 0.0273(10) 0.0267(11) 0.0325(11) -0.0007(8) 0.0044(8) 0.0094(8) C6 0.0169(8) 0.0283(10) 0.0288(10) 0.0066(8) -0.0047(7) -0.0077(7) C1 0.0176(8) 0.0165(9) 0.0206(8) 0.0028(7) 0.0020(6) -0.0010(6) O6 0.0268(8) 0.0644(13) 0.0431(10) -0.0171(9) 0.0070(7) -0.0162(8) N4 0.0261(9) 0.0335(11) 0.0418(11) 0.0185(9) -0.0063(8) -0.0101(8) C11 0.0231(10) 0.0527(15) 0.0270(10) 0.0036(10) 0.0024(8) -0.0010(9) O7 0.0745(15) 0.0459(11) 0.0420(11) -0.0130(9) 0.0143(10) -0.0252(10) O8 0.0505(12) 0.0460(12) 0.0781(15) 0.0334(11) -0.0321(11) -0.0167(9) C10 0.0409(13) 0.0373(13) 0.0461(14) -0.0231(11) -0.0141(11) 0.0147(10) Cl1 0.0263(2) 0.0163(2) 0.0266(2) -0.00109(17) 0.00050(17) -0.00105(16) O1 0.0564(12) 0.0231(8) 0.0485(11) 0.0005(7) 0.0174(9) 0.0054(8) O2 0.0381(10) 0.0496(11) 0.0497(11) 0.0004(9) 0.0134(8) -0.0098(9) O3 0.0525(12) 0.0624(14) 0.0485(12) -0.0127(10) -0.0106(9) -0.0191(10) O4 0.0802(15) 0.0244(9) 0.0437(10) 0.0049(8) -0.0079(10) 0.0100(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 Cl2 O8 1.4112(19) . ? Cl2 O7 1.4242(19) . ? Cl2 O5 1.4441(17) . ? Cl2 O6 1.4477(18) . ? N1 C1 1.336(2) . ? N1 N2 1.347(2) . ? N1 H111 0.85(3) . ? C2 C3 1.391(3) . ? C2 C1 1.400(2) . ? C2 C7 1.498(3) . ? C3 N2 1.341(3) . ? C3 C9 1.488(3) . ? N3 N4 1.334(3) . ? N3 C4 1.342(3) . ? N3 H333 0.71(3) . ? C8 C1 1.483(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C4 C5 1.394(3) . ? C4 C10 1.486(3) . ? N2 H222 0.80(3) . ? C7 C5 1.499(3) . ? C7 H7A 0.94(3) . ? C7 H7B 0.99(3) . ? C5 C6 1.395(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C6 N4 1.334(3) . ? C6 C11 1.485(3) . ? N4 H444 0.82(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? Cl1 O2 1.4173(18) . ? Cl1 O3 1.4283(19) . ? Cl1 O4 1.4379(18) . ? Cl1 O1 1.4461(17) . ? 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 O8 Cl2 O7 110.85(14) . . ? O8 Cl2 O5 109.19(11) . . ? O7 Cl2 O5 109.68(13) . . ? O8 Cl2 O6 111.51(15) . . ? O7 Cl2 O6 107.90(11) . . ? O5 Cl2 O6 107.64(11) . . ? C1 N1 N2 109.29(16) . . ? C1 N1 H111 131.6(17) . . ? N2 N1 H111 119.1(17) . . ? C3 C2 C1 106.24(17) . . ? C3 C2 C7 127.30(17) . . ? C1 C2 C7 126.46(17) . . ? N2 C3 C2 107.56(17) . . ? N2 C3 C9 121.60(18) . . ? C2 C3 C9 130.83(19) . . ? N4 N3 C4 109.7(2) . . ? N4 N3 H333 114(3) . . ? C4 N3 H333 135(3) . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C4 C5 107.2(2) . . ? N3 C4 C10 122.1(2) . . ? C5 C4 C10 130.7(2) . . ? C3 N2 N1 109.34(16) . . ? C3 N2 H222 128(2) . . ? N1 N2 H222 122(2) . . ? C2 C7 C5 112.30(16) . . ? C2 C7 H7A 109.2(16) . . ? C5 C7 H7A 112.0(16) . . ? C2 C7 H7B 109.6(14) . . ? C5 C7 H7B 108.1(15) . . ? H7A C7 H7B 105(2) . . ? C4 C5 C6 106.08(18) . . ? C4 C5 C7 126.84(19) . . ? C6 C5 C7 127.08(18) . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N4 C6 C5 107.7(2) . . ? N4 C6 C11 121.6(2) . . ? C5 C6 C11 130.7(2) . . ? N1 C1 C2 107.56(17) . . ? N1 C1 C8 121.32(17) . . ? C2 C1 C8 131.12(18) . . ? N3 N4 C6 109.3(2) . . ? N3 N4 H444 119(2) . . ? C6 N4 H444 132(2) . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 Cl1 O3 111.27(13) . . ? O2 Cl1 O4 111.10(13) . . ? O3 Cl1 O4 107.78(13) . . ? O2 Cl1 O1 109.37(11) . . ? O3 Cl1 O1 109.98(13) . . ? O4 Cl1 O1 107.24(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H111 O6 0.85(3) 1.92(3) 2.767(2) 176(3) . N2 H222 O1 0.80(3) 1.99(3) 2.786(3) 169(3) 6_656 N3 H333 O4 0.71(3) 2.15(3) 2.823(3) 159(4) 6_666 N4 H444 O5 0.82(3) 1.94(4) 2.753(3) 178(4) 4_565 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.62 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.999 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.079 # Attachment 'FORM-A.cif' data_09tba012_0m _database_code_depnum_ccdc_archive 'CCDC 742409' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H16 N4' _chemical_formula_weight 204.28 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' 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 7.2653(2) _cell_length_b 8.4142(2) _cell_length_c 9.8774(2) _cell_angle_alpha 99.3630(10) _cell_angle_beta 101.8060(10) _cell_angle_gamma 106.7770(10) _cell_volume 549.82(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2134 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 34.86 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.853349 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0305 before correction' _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 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10025 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 33.50 _reflns_number_total 4223 _reflns_number_gt 3265 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0930P)^2^+0.0635P] 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 4223 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1629 _refine_ls_wR_factor_gt 0.1535 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.06916(14) 0.31651(12) 0.30607(11) 0.0228(2) Uani 1 1 d . . . C1 C 0.21535(15) 0.32471(14) 0.24053(12) 0.0208(2) Uani 1 1 d . . . C5 C 0.59289(15) 0.71265(14) 0.21244(12) 0.0208(2) Uani 1 1 d . . . N2 N 0.11913(15) 0.46730(12) 0.40238(11) 0.0242(2) Uani 1 1 d . . . C2 C 0.36301(15) 0.48356(13) 0.29506(12) 0.0205(2) Uani 1 1 d . . . N3 N 0.74940(14) 0.98006(13) 0.20615(12) 0.0265(2) Uani 1 1 d . . . C4 C 0.77310(15) 0.84812(14) 0.25907(12) 0.0216(2) Uani 1 1 d . . . C3 C 0.29687(17) 0.56970(14) 0.39765(12) 0.0228(2) Uani 1 1 d . . . C6 C 0.46231(16) 0.77185(17) 0.12691(13) 0.0254(2) Uani 1 1 d . . . N4 N 0.55875(15) 0.93349(15) 0.12557(13) 0.0299(2) Uani 1 1 d . . . H444 H 0.5081 0.9971 0.0810 0.036 Uiso 0.50 1 calc PR . . C7 C 0.55208(18) 0.54247(16) 0.24992(18) 0.0316(3) Uani 1 1 d . . . C10 C 0.97033(18) 0.85324(18) 0.34556(14) 0.0299(3) Uani 1 1 d . . . C9 C 0.3945(2) 0.74471(16) 0.49286(15) 0.0316(3) Uani 1 1 d . . . C8 C 0.2057(2) 0.17819(17) 0.12859(15) 0.0321(3) Uani 1 1 d . . . C11 C 0.24948(18) 0.6835(2) 0.04415(17) 0.0376(3) Uani 1 1 d . . . H8C H 0.090(3) 0.084(3) 0.115(2) 0.048(5) Uiso 1 1 d . . . H9C H 0.532(4) 0.765(3) 0.540(3) 0.066(7) Uiso 1 1 d . . . H7B H 0.665(3) 0.547(3) 0.319(2) 0.051(6) Uiso 1 1 d . . . H9B H 0.326(3) 0.763(3) 0.563(2) 0.048(5) Uiso 1 1 d . . . H7A H 0.545(3) 0.448(3) 0.163(2) 0.058(6) Uiso 1 1 d . . . H9A H 0.395(3) 0.832(3) 0.436(2) 0.053(6) Uiso 1 1 d . . . H10C H 0.958(3) 0.823(3) 0.440(2) 0.043(5) Uiso 1 1 d . . . H10B H 1.023(3) 0.775(3) 0.290(2) 0.042(5) Uiso 1 1 d . . . H8B H 0.320(4) 0.135(3) 0.161(2) 0.060(6) Uiso 1 1 d . . . H10A H 1.071(3) 0.967(3) 0.368(2) 0.055(6) Uiso 1 1 d . . . H8A H 0.210(4) 0.209(3) 0.033(3) 0.067(7) Uiso 1 1 d . . . H11C H 0.221(4) 0.564(3) -0.001(3) 0.062(7) Uiso 1 1 d . . . H11B H 0.160(4) 0.667(3) 0.105(3) 0.060(6) Uiso 1 1 d . . . H11A H 0.212(4) 0.741(4) -0.017(3) 0.085(9) Uiso 1 1 d . . . H111 H -0.046(4) 0.238(4) 0.283(3) 0.017(6) Uiso 0.50 1 d P . . H222 H 0.055(4) 0.492(4) 0.458(3) 0.017(6) Uiso 0.50 1 d P . . H333 H 0.836(5) 1.085(4) 0.239(3) 0.019(7) Uiso 0.50 1 d P . . 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 0.0223(4) 0.0178(4) 0.0251(4) 0.0032(3) 0.0085(3) 0.0015(3) C1 0.0223(4) 0.0185(4) 0.0210(5) 0.0049(4) 0.0068(4) 0.0049(3) C5 0.0186(4) 0.0200(5) 0.0240(5) 0.0069(4) 0.0072(3) 0.0048(3) N2 0.0314(5) 0.0186(4) 0.0220(4) 0.0046(3) 0.0098(4) 0.0056(3) C2 0.0196(4) 0.0172(4) 0.0246(5) 0.0074(4) 0.0054(3) 0.0048(3) N3 0.0209(4) 0.0202(4) 0.0369(6) 0.0089(4) 0.0076(4) 0.0035(3) C4 0.0202(4) 0.0217(5) 0.0220(5) 0.0048(4) 0.0069(3) 0.0050(4) C3 0.0274(5) 0.0172(4) 0.0220(5) 0.0058(4) 0.0025(4) 0.0070(4) C6 0.0194(4) 0.0348(6) 0.0254(5) 0.0128(4) 0.0088(4) 0.0091(4) N4 0.0219(4) 0.0389(6) 0.0359(6) 0.0235(5) 0.0099(4) 0.0109(4) C7 0.0233(5) 0.0229(5) 0.0553(8) 0.0179(5) 0.0166(5) 0.0085(4) C10 0.0228(5) 0.0322(6) 0.0301(6) 0.0055(5) 0.0025(4) 0.0063(4) C9 0.0355(6) 0.0202(5) 0.0319(6) -0.0008(4) 0.0012(5) 0.0080(4) C8 0.0340(6) 0.0246(6) 0.0329(6) -0.0026(5) 0.0128(5) 0.0052(5) C11 0.0196(5) 0.0552(9) 0.0366(7) 0.0192(7) 0.0042(5) 0.0080(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3438(14) . ? N1 N2 1.3589(14) . ? N1 H111 0.86(3) . ? C1 C2 1.3888(14) . ? C1 C8 1.4908(17) . ? C5 C6 1.3941(16) . ? C5 C4 1.3952(14) . ? C5 C7 1.4992(16) . ? N2 C3 1.3445(15) . ? N2 H222 0.83(3) . ? C2 C3 1.3944(16) . ? C2 C7 1.5037(15) . ? N3 C4 1.3407(15) . ? N3 N4 1.3564(14) . ? N3 H333 0.89(3) . ? C4 C10 1.4955(16) . ? C3 C9 1.4931(16) . ? C6 N4 1.3418(17) . ? C6 C11 1.4944(17) . ? N4 H444 0.8600 . ? C7 H7B 0.94(2) . ? C7 H7A 1.05(2) . ? C10 H10C 1.02(2) . ? C10 H10B 0.99(2) . ? C10 H10A 0.98(2) . ? C9 H9C 0.96(2) . ? C9 H9B 0.95(2) . ? C9 H9A 1.00(2) . ? C8 H8C 0.94(2) . ? C8 H8B 1.02(2) . ? C8 H8A 1.02(3) . ? C11 H11C 0.97(3) . ? C11 H11B 0.97(2) . ? C11 H11A 0.88(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 C1 N1 N2 108.34(9) . . ? C1 N1 H111 126.7(19) . . ? N2 N1 H111 124.2(19) . . ? N1 C1 C2 109.13(10) . . ? N1 C1 C8 121.59(10) . . ? C2 C1 C8 129.28(10) . . ? C6 C5 C4 105.03(10) . . ? C6 C5 C7 128.48(10) . . ? C4 C5 C7 126.49(11) . . ? C3 N2 N1 108.60(10) . . ? C3 N2 H222 125(2) . . ? N1 N2 H222 127(2) . . ? C1 C2 C3 105.17(9) . . ? C1 C2 C7 125.49(11) . . ? C3 C2 C7 129.34(10) . . ? C4 N3 N4 108.54(9) . . ? C4 N3 H333 122(2) . . ? N4 N3 H333 127(2) . . ? N3 C4 C5 108.91(10) . . ? N3 C4 C10 122.24(10) . . ? C5 C4 C10 128.73(11) . . ? N2 C3 C2 108.76(10) . . ? N2 C3 C9 121.66(11) . . ? C2 C3 C9 129.59(11) . . ? N4 C6 C5 108.78(10) . . ? N4 C6 C11 121.04(12) . . ? C5 C6 C11 130.18(12) . . ? C6 N4 N3 108.72(10) . . ? C6 N4 H444 125.6 . . ? N3 N4 H444 125.6 . . ? C5 C7 C2 114.55(10) . . ? C5 C7 H7B 107.7(13) . . ? C2 C7 H7B 112.5(13) . . ? C5 C7 H7A 110.0(13) . . ? C2 C7 H7A 108.2(13) . . ? H7B C7 H7A 103.4(18) . . ? C4 C10 H10C 110.5(11) . . ? C4 C10 H10B 109.8(11) . . ? H10C C10 H10B 111.7(15) . . ? C4 C10 H10A 112.2(13) . . ? H10C C10 H10A 107.1(17) . . ? H10B C10 H10A 105.5(17) . . ? C3 C9 H9C 112.3(15) . . ? C3 C9 H9B 111.0(13) . . ? H9C C9 H9B 108.5(18) . . ? C3 C9 H9A 110.1(13) . . ? H9C C9 H9A 106.2(19) . . ? H9B C9 H9A 108.5(18) . . ? C1 C8 H8C 111.2(13) . . ? C1 C8 H8B 109.8(13) . . ? H8C C8 H8B 104.7(17) . . ? C1 C8 H8A 112.8(14) . . ? H8C C8 H8A 108.8(18) . . ? H8B C8 H8A 109.2(18) . . ? C6 C11 H11C 113.2(14) . . ? C6 C11 H11B 112.6(14) . . ? H11C C11 H11B 98.5(19) . . ? C6 C11 H11A 110.8(19) . . ? H11C C11 H11A 112(2) . . ? H11B C11 H11A 109(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H111 N3 0.86(3) 2.15(3) 2.9566(14) 155(3) 1_445 N2 H222 N2 0.83(3) 2.10(3) 2.931(2) 175(3) 2_566 N3 H333 N1 0.89(3) 2.08(3) 2.9566(14) 171(3) 1_665 N4 H444 N4 0.86 2.21 2.954(2) 144.5 2_675 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 33.50 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.493 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.056 # Attachment 'FORM-B.cif' data_09tba028_0m _database_code_depnum_ccdc_archive 'CCDC 742410' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H16 N4' _chemical_formula_weight 204.28 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' 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.2313(3) _cell_length_b 16.1062(7) _cell_length_c 17.0904(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2265.76(16) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4142 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 25.61 _exptl_crystal_description Cube _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.882810 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0483 before correction' _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 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 25866 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 25.52 _reflns_number_total 2106 _reflns_number_gt 1717 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0706P)^2^+0.7192P] 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 2106 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.1264 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.0067(2) 0.89347(8) 0.33961(9) 0.0322(4) Uani 1 1 d . . . H1A H -0.0299 0.8458 0.3171 0.039 Uiso 1 1 calc R . . N2 N 0.1413(2) 0.91485(9) 0.36829(9) 0.0323(4) Uani 1 1 d . . . C5 C -0.0269(2) 1.17709(9) 0.37412(10) 0.0245(4) Uani 1 1 d . . . N3 N 0.1026(2) 1.29554(9) 0.35332(9) 0.0351(4) Uani 1 1 d . . . H3A H 0.1577 1.3416 0.3614 0.042 Uiso 1 1 calc R . . C2 C -0.0303(2) 1.02019(10) 0.38807(9) 0.0242(4) Uani 1 1 d . . . N4 N 0.0489(2) 1.26874(9) 0.28250(9) 0.0358(4) Uani 1 1 d . . . C1 C -0.1120(2) 0.95571(10) 0.35070(10) 0.0273(4) Uani 1 1 d . . . C6 C -0.0304(2) 1.19723(10) 0.29444(10) 0.0281(4) Uani 1 1 d . . . C3 C 0.1280(2) 0.99180(10) 0.39819(9) 0.0268(4) Uani 1 1 d . . . C7 C -0.1007(2) 1.10230(10) 0.41306(11) 0.0276(4) Uani 1 1 d . . . C4 C 0.0592(2) 1.24123(10) 0.40918(10) 0.0295(4) Uani 1 1 d . . . C11 C -0.1020(3) 1.15069(13) 0.22756(12) 0.0376(5) Uani 1 1 d . . . C9 C 0.2683(3) 1.03219(13) 0.43803(11) 0.0348(5) Uani 1 1 d . . . C8 C -0.2847(3) 0.94843(14) 0.32571(13) 0.0390(5) Uani 1 1 d . . . C10 C 0.1029(3) 1.25511(14) 0.49287(13) 0.0440(6) Uani 1 1 d . . . H7B H -0.082(2) 1.1063(12) 0.4654(13) 0.035(5) Uiso 1 1 d . . . H7A H -0.225(3) 1.1018(12) 0.3999(11) 0.038(5) Uiso 1 1 d . . . H11C H -0.048(3) 1.0993(17) 0.2209(15) 0.067(8) Uiso 1 1 d . . . H9C H 0.244(3) 1.0461(15) 0.4956(16) 0.072(8) Uiso 1 1 d . . . H9B H 0.291(3) 1.0866(17) 0.4169(15) 0.063(7) Uiso 1 1 d . . . H8C H -0.306(3) 0.9801(17) 0.2807(17) 0.071(8) Uiso 1 1 d . . . H11B H -0.102(4) 1.1857(19) 0.1826(18) 0.084(9) Uiso 1 1 d . . . H11A H -0.215(4) 1.1347(16) 0.2384(15) 0.072(8) Uiso 1 1 d . . . H8B H -0.364(4) 0.9713(19) 0.3622(19) 0.092(10) Uiso 1 1 d . . . H8A H -0.303(3) 0.8925(19) 0.3149(16) 0.077(9) Uiso 1 1 d . . . H9A H 0.363(4) 0.9972(18) 0.4367(15) 0.073(8) Uiso 1 1 d . . . H10B H 0.082(4) 1.305(2) 0.5113(19) 0.102(11) Uiso 1 1 d . . . H10A H 0.039(5) 1.219(2) 0.534(2) 0.129(13) Uiso 1 1 d . . . H10C H 0.201(5) 1.234(2) 0.504(2) 0.113(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0455(10) 0.0239(7) 0.0272(8) -0.0035(6) 0.0026(7) -0.0007(7) N2 0.0404(9) 0.0275(7) 0.0290(8) 0.0010(6) 0.0024(7) 0.0050(7) C5 0.0250(9) 0.0200(8) 0.0284(9) -0.0013(6) 0.0010(7) 0.0022(7) N3 0.0372(9) 0.0249(7) 0.0432(9) 0.0051(6) -0.0064(7) -0.0072(7) C2 0.0302(10) 0.0219(8) 0.0205(8) 0.0011(6) 0.0038(7) -0.0012(7) N4 0.0411(10) 0.0251(8) 0.0411(9) 0.0059(6) -0.0075(8) -0.0020(7) C1 0.0338(10) 0.0252(8) 0.0228(8) 0.0006(6) 0.0051(7) -0.0019(7) C6 0.0295(10) 0.0217(8) 0.0330(9) 0.0014(7) -0.0047(7) 0.0020(7) C3 0.0339(10) 0.0256(8) 0.0208(8) 0.0024(6) 0.0051(7) 0.0017(7) C7 0.0324(11) 0.0230(8) 0.0274(10) -0.0022(7) 0.0047(8) -0.0012(7) C4 0.0313(10) 0.0261(8) 0.0310(10) -0.0007(7) -0.0008(8) -0.0014(7) C11 0.0510(14) 0.0309(10) 0.0310(11) 0.0011(8) -0.0092(9) -0.0009(9) C9 0.0322(11) 0.0408(11) 0.0312(11) 0.0032(8) 0.0001(8) -0.0018(9) C8 0.0384(13) 0.0396(11) 0.0390(12) -0.0059(9) -0.0026(9) -0.0088(9) C10 0.0599(16) 0.0365(11) 0.0357(11) -0.0057(9) -0.0079(11) -0.0086(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 N1 C1 1.339(2) . ? N1 N2 1.357(2) . ? N1 H1A 0.8800 . ? N2 C3 1.345(2) . ? C5 C4 1.389(2) . ? C5 C6 1.400(2) . ? C5 C7 1.504(2) . ? N3 C4 1.343(2) . ? N3 N4 1.359(2) . ? N3 H3A 0.8800 . ? C2 C1 1.392(2) . ? C2 C3 1.392(3) . ? C2 C7 1.506(2) . ? N4 C6 1.339(2) . ? C1 C8 1.489(3) . ? C6 C11 1.488(3) . ? C3 C9 1.490(3) . ? C7 H7B 0.91(2) . ? C7 H7A 1.05(2) . ? C4 C10 1.492(3) . ? C11 H11C 0.95(3) . ? C11 H11B 0.95(3) . ? C11 H11A 0.99(3) . ? C9 H9C 1.03(3) . ? C9 H9B 0.96(3) . ? C9 H9A 0.96(3) . ? C8 H8C 0.94(3) . ? C8 H8B 0.98(3) . ? C8 H8A 0.93(3) . ? C10 H10B 0.88(4) . ? C10 H10A 1.05(4) . ? C10 H10C 0.89(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 N2 109.87(14) . . ? C1 N1 H1A 125.1 . . ? N2 N1 H1A 125.1 . . ? C3 N2 N1 107.35(14) . . ? C4 C5 C6 104.94(14) . . ? C4 C5 C7 127.65(16) . . ? C6 C5 C7 127.42(15) . . ? C4 N3 N4 109.85(14) . . ? C4 N3 H3A 125.1 . . ? N4 N3 H3A 125.1 . . ? C1 C2 C3 105.32(15) . . ? C1 C2 C7 126.85(16) . . ? C3 C2 C7 127.83(16) . . ? C6 N4 N3 107.22(14) . . ? N1 C1 C2 108.11(16) . . ? N1 C1 C8 121.24(16) . . ? C2 C1 C8 130.65(17) . . ? N4 C6 C5 109.72(15) . . ? N4 C6 C11 120.60(16) . . ? C5 C6 C11 129.66(16) . . ? N2 C3 C2 109.35(16) . . ? N2 C3 C9 120.88(16) . . ? C2 C3 C9 129.71(16) . . ? C5 C7 C2 115.01(14) . . ? C5 C7 H7B 108.2(12) . . ? C2 C7 H7B 106.1(12) . . ? C5 C7 H7A 107.8(10) . . ? C2 C7 H7A 107.9(11) . . ? H7B C7 H7A 111.9(16) . . ? N3 C4 C5 108.27(15) . . ? N3 C4 C10 121.32(17) . . ? C5 C4 C10 130.41(17) . . ? C6 C11 H11C 110.2(16) . . ? C6 C11 H11B 108.7(18) . . ? H11C C11 H11B 115(2) . . ? C6 C11 H11A 111.3(15) . . ? H11C C11 H11A 104(2) . . ? H11B C11 H11A 108(2) . . ? C3 C9 H9C 112.3(16) . . ? C3 C9 H9B 112.0(15) . . ? H9C C9 H9B 101.3(19) . . ? C3 C9 H9A 111.2(16) . . ? H9C C9 H9A 108(2) . . ? H9B C9 H9A 112(2) . . ? C1 C8 H8C 111.6(16) . . ? C1 C8 H8B 115.3(19) . . ? H8C C8 H8B 101(2) . . ? C1 C8 H8A 106.9(18) . . ? H8C C8 H8A 109(2) . . ? H8B C8 H8A 112(3) . . ? C4 C10 H10B 116(2) . . ? C4 C10 H10A 116(2) . . ? H10B C10 H10A 100(3) . . ? C4 C10 H10C 111(2) . . ? H10B C10 H10C 117(3) . . ? H10A C10 H10C 96(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 C1 N1 N2 C3 0.27(18) . . . . ? C4 N3 N4 C6 0.6(2) . . . . ? N2 N1 C1 C2 -0.07(19) . . . . ? N2 N1 C1 C8 -179.11(16) . . . . ? C3 C2 C1 N1 -0.14(18) . . . . ? C7 C2 C1 N1 -179.24(15) . . . . ? C3 C2 C1 C8 178.78(18) . . . . ? C7 C2 C1 C8 -0.3(3) . . . . ? N3 N4 C6 C5 -0.4(2) . . . . ? N3 N4 C6 C11 -178.81(17) . . . . ? C4 C5 C6 N4 0.1(2) . . . . ? C7 C5 C6 N4 -179.93(16) . . . . ? C4 C5 C6 C11 178.3(2) . . . . ? C7 C5 C6 C11 -1.7(3) . . . . ? N1 N2 C3 C2 -0.35(18) . . . . ? N1 N2 C3 C9 177.03(15) . . . . ? C1 C2 C3 N2 0.31(18) . . . . ? C7 C2 C3 N2 179.39(15) . . . . ? C1 C2 C3 C9 -176.77(17) . . . . ? C7 C2 C3 C9 2.3(3) . . . . ? C4 C5 C7 C2 -116.6(2) . . . . ? C6 C5 C7 C2 63.5(2) . . . . ? C1 C2 C7 C5 -117.58(19) . . . . ? C3 C2 C7 C5 63.5(2) . . . . ? N4 N3 C4 C5 -0.5(2) . . . . ? N4 N3 C4 C10 179.88(19) . . . . ? C6 C5 C4 N3 0.23(19) . . . . ? C7 C5 C4 N3 -179.71(16) . . . . ? C6 C5 C4 C10 179.8(2) . . . . ? C7 C5 C4 C10 -0.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A N4 0.88 2.11 2.917(2) 151.8 3_545 N3 H3A N2 0.88 2.04 2.864(2) 156.4 8_665 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.52 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.290 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.043 # Attachment 'TFA.cif' data_rm16 _database_code_depnum_ccdc_archive 'CCDC 742411' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 F6 N4 O4' _chemical_formula_weight 432.33 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.3698(9) _cell_length_b 13.6543(8) _cell_length_c 18.7565(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3936.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4065 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 25.1 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1776 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.833942 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0706 before correction' _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 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 52216 _diffrn_reflns_av_R_equivalents 0.0873 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.53 _reflns_number_total 3638 _reflns_number_gt 2734 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0851P)^2^+4.8529P] 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 3638 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0796 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1714 _refine_ls_wR_factor_gt 0.1563 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.03877(15) 0.51306(17) 0.09380(13) 0.0272(5) Uani 1 1 d . . . N2 N -0.03599(16) 0.56294(17) 0.09934(12) 0.0252(5) Uani 1 1 d . . . O1 O 0.30348(13) 0.99569(16) -0.06387(11) 0.0361(5) Uani 1 1 d . . . O2 O 0.16720(13) 1.03237(17) -0.09487(11) 0.0407(6) Uani 1 1 d . . . N3 N 0.07532(15) 0.98395(18) 0.07441(12) 0.0265(5) Uani 1 1 d . . . O3 O 0.03610(15) 0.16783(14) 0.03933(11) 0.0387(6) Uani 1 1 d . . . N4 N 0.12291(15) 0.93814(17) 0.02445(13) 0.0267(5) Uani 1 1 d . . . F4 F 0.13286(15) 0.17862(17) 0.15924(12) 0.0628(7) Uani 1 1 d . . . C2 C 0.06956(17) 0.66044(18) 0.13482(14) 0.0224(6) Uani 1 1 d . . . F1 F 0.30580(16) 0.9985(2) -0.21752(11) 0.0697(7) Uani 1 1 d . . . O4 O 0.02977(16) 0.33089(14) 0.04389(11) 0.0414(6) Uani 1 1 d . . . C3 C -0.01996(17) 0.65305(19) 0.12328(13) 0.0232(6) Uani 1 1 d . . . C5 C 0.10912(17) 0.83790(19) 0.11602(14) 0.0235(6) Uani 1 1 d . . . C4 C 0.06604(17) 0.92471(19) 0.13107(14) 0.0245(6) Uani 1 1 d . . . F5 F 0.0965(2) 0.32873(15) 0.17339(12) 0.0841(10) Uani 1 1 d . . . F2 F 0.22242(17) 1.1202(3) -0.21108(14) 0.1016(12) Uani 1 1 d . . . C10 C 0.0147(2) 0.9567(2) 0.19435(16) 0.0313(7) Uani 1 1 d . . . F3 F 0.35225(18) 1.12491(19) -0.16562(13) 0.0757(8) Uani 1 1 d . . . F6 F 0.00602(19) 0.2160(2) 0.18838(12) 0.0781(8) Uani 1 1 d . . . C13 C 0.2467(2) 1.0298(2) -0.10345(15) 0.0301(7) Uani 1 1 d . . . C1 C 0.10453(18) 0.5703(2) 0.11561(14) 0.0253(6) Uani 1 1 d . . . C6 C 0.14393(17) 0.8490(2) 0.04749(14) 0.0254(6) Uani 1 1 d . . . C9 C -0.0905(2) 0.7258(2) 0.13192(18) 0.0305(7) Uani 1 1 d . . . C15 C 0.04369(19) 0.2485(2) 0.06850(15) 0.0278(6) Uani 1 1 d . . . C11 C 0.1938(3) 0.7795(3) 0.00249(19) 0.0381(8) Uani 1 1 d . . . C14 C 0.0728(2) 0.2447(2) 0.14673(16) 0.0352(7) Uani 1 1 d . . . C7 C 0.11751(19) 0.7487(2) 0.16254(15) 0.0261(6) Uani 1 1 d . . . C8 C 0.19601(19) 0.5339(2) 0.11549(17) 0.0339(7) Uani 1 1 d . . . H8A H 0.1972 0.4674 0.0988 0.051 Uiso 1 1 calc R . . H8B H 0.2191 0.5366 0.1630 0.051 Uiso 1 1 calc R . . H8C H 0.2307 0.5741 0.0846 0.051 Uiso 1 1 calc R . . C12 C 0.2805(2) 1.0716(3) -0.17448(18) 0.0454(9) Uani 1 1 d . . . H7A H 0.099(2) 0.765(2) 0.2104(19) 0.038(9) Uiso 1 1 d . . . H7B H 0.179(2) 0.728(2) 0.1669(17) 0.035(8) Uiso 1 1 d . . . H9A H -0.084(2) 0.774(3) 0.095(2) 0.050(10) Uiso 1 1 d . . . H333 H 0.061(2) 1.047(2) 0.0665(16) 0.029(8) Uiso 1 1 d . . . H9B H -0.088(2) 0.761(3) 0.174(2) 0.049(10) Uiso 1 1 d . . . H9C H -0.147(2) 0.695(3) 0.1327(17) 0.040(9) Uiso 1 1 d . . . H10A H 0.022(2) 0.910(3) 0.233(2) 0.053(10) Uiso 1 1 d . . . H111 H 0.039(2) 0.446(3) 0.0784(18) 0.040(9) Uiso 1 1 d . . . H222 H -0.084(2) 0.539(3) 0.0861(18) 0.038(10) Uiso 1 1 d . . . H11A H 0.238(3) 0.754(3) 0.028(2) 0.058(12) Uiso 1 1 d . . . H11B H 0.214(3) 0.814(3) -0.036(2) 0.071(13) Uiso 1 1 d . . . H10B H -0.041(3) 0.958(3) 0.185(2) 0.071(14) Uiso 1 1 d . . . H10C H 0.037(3) 1.022(4) 0.212(3) 0.091(16) Uiso 1 1 d . . . H444 H 0.139(3) 0.965(3) -0.016(2) 0.064(12) Uiso 1 1 d . . . H11C H 0.158(3) 0.725(4) -0.012(3) 0.080(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0280(13) 0.0187(12) 0.0348(13) -0.0016(10) -0.0028(10) 0.0018(10) N2 0.0247(13) 0.0203(12) 0.0306(12) 0.0014(10) -0.0027(10) -0.0031(10) O1 0.0288(11) 0.0459(13) 0.0335(11) 0.0111(10) 0.0051(9) 0.0097(10) O2 0.0271(12) 0.0561(15) 0.0388(12) 0.0161(11) 0.0050(9) 0.0076(10) N3 0.0291(13) 0.0195(12) 0.0308(12) -0.0002(10) -0.0016(10) -0.0004(10) O3 0.0627(15) 0.0191(11) 0.0343(11) -0.0022(9) -0.0114(10) -0.0019(10) N4 0.0284(13) 0.0230(12) 0.0287(12) 0.0020(10) 0.0026(10) -0.0043(10) F4 0.0718(15) 0.0592(14) 0.0575(13) -0.0092(10) -0.0305(11) 0.0304(12) C2 0.0257(14) 0.0174(13) 0.0241(13) 0.0034(10) -0.0011(11) -0.0013(11) F1 0.0690(16) 0.1008(19) 0.0392(11) -0.0092(12) 0.0171(11) 0.0095(14) O4 0.0717(17) 0.0181(11) 0.0343(11) 0.0009(9) -0.0106(11) -0.0005(10) C3 0.0270(14) 0.0196(13) 0.0229(13) 0.0039(11) -0.0010(11) -0.0008(11) C5 0.0236(13) 0.0202(13) 0.0267(13) -0.0024(11) -0.0024(11) -0.0043(11) C4 0.0233(14) 0.0211(14) 0.0290(14) -0.0003(11) -0.0038(11) -0.0044(11) F5 0.165(3) 0.0322(12) 0.0556(13) -0.0053(10) -0.0517(16) -0.0056(14) F2 0.0730(17) 0.159(3) 0.0731(16) 0.0786(19) 0.0344(14) 0.0633(18) C10 0.0333(18) 0.0306(17) 0.0299(15) -0.0012(13) 0.0002(13) 0.0031(14) F3 0.0881(18) 0.0749(17) 0.0642(15) 0.0149(12) 0.0246(13) -0.0327(15) F6 0.0882(18) 0.100(2) 0.0461(13) 0.0113(13) 0.0241(12) 0.0120(16) C13 0.0315(16) 0.0279(15) 0.0310(14) 0.0046(12) 0.0074(12) 0.0069(13) C1 0.0270(15) 0.0206(13) 0.0282(13) 0.0044(11) -0.0015(11) 0.0009(11) C6 0.0226(14) 0.0233(14) 0.0302(14) -0.0003(11) -0.0014(11) -0.0035(11) C9 0.0267(17) 0.0265(15) 0.0383(17) 0.0008(14) -0.0009(13) 0.0023(12) C15 0.0327(15) 0.0218(15) 0.0289(14) 0.0001(12) 0.0004(12) -0.0011(12) C11 0.043(2) 0.0336(18) 0.0382(18) 0.0000(15) 0.0091(16) 0.0038(16) C14 0.0494(19) 0.0240(15) 0.0324(16) -0.0023(12) -0.0022(14) 0.0077(14) C7 0.0280(16) 0.0212(14) 0.0291(15) -0.0007(11) -0.0037(12) -0.0019(12) C8 0.0286(16) 0.0286(16) 0.0446(17) 0.0004(13) -0.0008(13) 0.0053(13) C12 0.0353(18) 0.058(2) 0.0424(19) 0.0179(17) 0.0115(15) 0.0144(17) _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 N2 1.340(3) . ? N1 C1 1.341(4) . ? N1 H111 0.97(4) . ? N2 C3 1.333(4) . ? N2 H222 0.84(4) . ? O1 C13 1.236(4) . ? O2 C13 1.234(4) . ? N3 N4 1.343(3) . ? N3 C4 1.343(4) . ? N3 H333 0.90(3) . ? O3 C15 1.236(3) . ? N4 C6 1.331(4) . ? N4 H444 0.88(4) . ? F4 C14 1.313(4) . ? C2 C1 1.391(4) . ? C2 C3 1.397(4) . ? C2 C7 1.505(4) . ? F1 C12 1.341(4) . ? O4 C15 1.234(3) . ? C3 C9 1.480(4) . ? C5 C4 1.387(4) . ? C5 C6 1.401(4) . ? C5 C7 1.504(4) . ? C4 C10 1.490(4) . ? F5 C14 1.303(4) . ? F2 C12 1.307(4) . ? C10 H10A 0.98(4) . ? C10 H10B 0.88(5) . ? C10 H10C 1.02(5) . ? F3 C12 1.332(4) . ? F6 C14 1.348(4) . ? C13 C12 1.539(4) . ? C1 C8 1.491(4) . ? C6 C11 1.484(4) . ? C9 H9A 0.96(4) . ? C9 H9B 0.93(4) . ? C9 H9C 0.96(4) . ? C15 C14 1.535(4) . ? C11 H11A 0.90(4) . ? C11 H11B 0.92(5) . ? C11 H11C 0.95(5) . ? C7 H7A 0.97(3) . ? C7 H7B 0.99(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? 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 N2 N1 C1 109.1(2) . . ? N2 N1 H111 121(2) . . ? C1 N1 H111 130(2) . . ? C3 N2 N1 109.7(2) . . ? C3 N2 H222 128(2) . . ? N1 N2 H222 122(2) . . ? N4 N3 C4 109.2(2) . . ? N4 N3 H333 118(2) . . ? C4 N3 H333 133(2) . . ? C6 N4 N3 109.4(2) . . ? C6 N4 H444 126(3) . . ? N3 N4 H444 124(3) . . ? C1 C2 C3 106.1(2) . . ? C1 C2 C7 127.5(2) . . ? C3 C2 C7 126.4(2) . . ? N2 C3 C2 107.5(2) . . ? N2 C3 C9 121.4(3) . . ? C2 C3 C9 131.0(3) . . ? C4 C5 C6 106.0(2) . . ? C4 C5 C7 128.0(3) . . ? C6 C5 C7 126.0(2) . . ? N3 C4 C5 107.6(2) . . ? N3 C4 C10 120.7(3) . . ? C5 C4 C10 131.7(3) . . ? C4 C10 H10A 110(2) . . ? C4 C10 H10B 112(3) . . ? H10A C10 H10B 106(4) . . ? C4 C10 H10C 110(3) . . ? H10A C10 H10C 107(3) . . ? H10B C10 H10C 112(4) . . ? O2 C13 O1 129.2(3) . . ? O2 C13 C12 115.9(3) . . ? O1 C13 C12 114.9(3) . . ? N1 C1 C2 107.7(2) . . ? N1 C1 C8 121.0(2) . . ? C2 C1 C8 131.3(3) . . ? N4 C6 C5 107.7(2) . . ? N4 C6 C11 121.7(3) . . ? C5 C6 C11 130.5(3) . . ? C3 C9 H9A 108(2) . . ? C3 C9 H9B 114(2) . . ? H9A C9 H9B 105(3) . . ? C3 C9 H9C 112(2) . . ? H9A C9 H9C 114(3) . . ? H9B C9 H9C 104(3) . . ? O4 C15 O3 129.1(3) . . ? O4 C15 C14 116.0(2) . . ? O3 C15 C14 114.9(2) . . ? C6 C11 H11A 110(3) . . ? C6 C11 H11B 107(3) . . ? H11A C11 H11B 111(4) . . ? C6 C11 H11C 111(3) . . ? H11A C11 H11C 106(4) . . ? H11B C11 H11C 111(4) . . ? F5 C14 F4 109.8(3) . . ? F5 C14 F6 104.3(3) . . ? F4 C14 F6 103.4(3) . . ? F5 C14 C15 114.7(2) . . ? F4 C14 C15 113.5(2) . . ? F6 C14 C15 110.0(3) . . ? C5 C7 C2 114.0(2) . . ? C5 C7 H7A 108.7(19) . . ? C2 C7 H7A 111(2) . . ? C5 C7 H7B 111.4(19) . . ? C2 C7 H7B 105.3(19) . . ? H7A C7 H7B 106(3) . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? F2 C12 F3 110.7(3) . . ? F2 C12 F1 105.1(3) . . ? F3 C12 F1 104.0(3) . . ? F2 C12 C13 114.4(3) . . ? F3 C12 C13 111.9(3) . . ? F1 C12 C13 110.1(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H111 O4 0.97(4) 1.70(4) 2.661(3) 173(3) . N2 H222 O1 0.84(4) 1.84(4) 2.678(3) 171(3) 4_465 N3 H333 O3 0.90(3) 1.77(3) 2.665(3) 173(3) 1_565 N4 H444 O2 0.88(4) 1.80(5) 2.670(3) 173(4) . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.53 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.755 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.062