# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Swagata Banerjee' 'Jonathan A. Kitchen' 'John M. Kelly' 'Thorfinnur Gunnlaugsson' _publ_contact_author_name 'Jonathan A. Kitchen' _publ_contact_author_email JKITCHEN@tcd.ie data_sb67 _database_code_depnum_ccdc_archive 'CCDC 843421' #TrackingRef 'SB67.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 F6 N3 O2 P' _chemical_formula_weight 463.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.4536(19) _cell_length_b 9.3865(19) _cell_length_c 21.293(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.03(3) _cell_angle_gamma 90.00 _cell_volume 1860.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 112(2) _cell_measurement_reflns_used 4005 _cell_measurement_theta_min 1.9424 _cell_measurement_theta_max 31.3254 _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.43 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.5575 _exptl_absorpt_process_details Crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 112(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 'Rigaku Saturn 724' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6793 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3184 _reflns_number_gt 3052 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0734P)^2^+2.7508P] 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 3184 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1512 _refine_ls_wR_factor_gt 0.1447 _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 O1 O 0.04515(18) 0.85881(19) 0.03802(8) 0.0214(4) Uani 1 1 d . . . O2 O 0.40945(19) 1.12811(19) 0.14510(8) 0.0228(4) Uani 1 1 d . . . N1 N 0.7747(2) 0.7067(2) -0.00059(11) 0.0266(5) Uani 1 1 d . . . H1X H 0.8703 0.7259 0.0113 0.032 Uiso 1 1 d . . . H1Y H 0.7445 0.6353 -0.0328 0.032 Uiso 1 1 d . . . N2 N 0.2282(2) 0.9917(2) 0.09120(9) 0.0163(4) Uani 1 1 d . . . N3 N 0.2108(2) 1.0291(2) 0.23046(10) 0.0184(5) Uani 1 1 d . . . C1 C 0.3748(3) 1.0278(3) 0.10828(11) 0.0175(5) Uani 1 1 d . . . C2 C 0.4758(3) 0.9416(3) 0.08150(11) 0.0167(5) Uani 1 1 d . . . C3 C 0.6224(3) 0.9675(3) 0.09726(12) 0.0206(5) Uani 1 1 d . . . H3 H 0.6559 1.0412 0.1267 0.025 Uiso 1 1 calc R . . C4 C 0.7210(3) 0.8876(3) 0.07076(12) 0.0216(5) Uani 1 1 d . . . H4 H 0.8207 0.9059 0.0835 0.026 Uiso 1 1 calc R . . C5 C 0.6767(3) 0.7803(3) 0.02545(12) 0.0212(5) Uani 1 1 d . . . C6 C 0.5257(3) 0.7516(3) 0.00739(12) 0.0206(5) Uani 1 1 d . . . C7 C 0.4694(3) 0.6488(3) -0.03930(13) 0.0254(6) Uani 1 1 d . . . H7 H 0.5337 0.5967 -0.0602 0.030 Uiso 1 1 calc R . . C8 C 0.3253(3) 0.6227(3) -0.05503(13) 0.0276(6) Uani 1 1 d . . . H8 H 0.2909 0.5536 -0.0866 0.033 Uiso 1 1 calc R . . C9 C 0.2288(3) 0.6976(3) -0.02471(12) 0.0233(6) Uani 1 1 d . . . H9 H 0.1290 0.6775 -0.0348 0.028 Uiso 1 1 calc R . . C10 C 0.2784(3) 0.8013(3) 0.01999(11) 0.0174(5) Uani 1 1 d . . . C11 C 0.4272(3) 0.8312(2) 0.03675(11) 0.0170(5) Uani 1 1 d . . . C12 C 0.1742(3) 0.8822(3) 0.04932(11) 0.0171(5) Uani 1 1 d . . . C13 C 0.1224(3) 1.0800(3) 0.11640(11) 0.0188(5) Uani 1 1 d . . . H13A H 0.0340 1.0868 0.0839 0.023 Uiso 1 1 calc R . . H13B H 0.1615 1.1774 0.1244 0.023 Uiso 1 1 calc R . . C14 C 0.0841(3) 1.0206(3) 0.17800(12) 0.0224(6) Uani 1 1 d . . . H14A H 0.0034 1.0758 0.1898 0.027 Uiso 1 1 calc R . . H14B H 0.0531 0.9202 0.1715 0.027 Uiso 1 1 calc R . . C15 C 0.2909(3) 0.9116(3) 0.24809(12) 0.0233(6) Uani 1 1 d . . . H15 H 0.2605 0.8217 0.2302 0.028 Uiso 1 1 calc R . . C16 C 0.4162(3) 0.9220(3) 0.29189(13) 0.0291(6) Uani 1 1 d . . . H16 H 0.4720 0.8395 0.3049 0.035 Uiso 1 1 calc R . . C17 C 0.4597(3) 1.0548(3) 0.31672(13) 0.0304(6) Uani 1 1 d . . . H17 H 0.5476 1.0644 0.3458 0.036 Uiso 1 1 calc R . . C18 C 0.3756(3) 1.1725(3) 0.29919(13) 0.0287(6) Uani 1 1 d . . . H18 H 0.4034 1.2631 0.3170 0.034 Uiso 1 1 calc R . . C19 C 0.2509(3) 1.1579(3) 0.25567(12) 0.0233(6) Uani 1 1 d . . . H19 H 0.1926 1.2389 0.2432 0.028 Uiso 1 1 calc R . . P1 P 0.10629(7) 0.53203(7) 0.16054(3) 0.0228(2) Uani 1 1 d . . . F1 F 0.20744(17) 0.66053(16) 0.14535(7) 0.0261(4) Uani 1 1 d . . . F2 F 0.0078(2) 0.4032(2) 0.17685(11) 0.0485(5) Uani 1 1 d . . . F3 F -0.0077(3) 0.6432(2) 0.17576(16) 0.0763(9) Uani 1 1 d . . . F4 F 0.0330(3) 0.5274(3) 0.08780(11) 0.0655(7) Uani 1 1 d . . . F5 F 0.2237(2) 0.42113(19) 0.14503(12) 0.0510(6) Uani 1 1 d . . . F6 F 0.1858(3) 0.5331(3) 0.23285(9) 0.0658(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0191(9) 0.0206(9) 0.0244(9) 0.0013(7) 0.0030(7) -0.0028(7) O2 0.0270(9) 0.0209(9) 0.0213(9) -0.0053(7) 0.0063(7) -0.0062(7) N1 0.0213(11) 0.0250(12) 0.0344(12) -0.0029(10) 0.0075(9) -0.0007(9) N2 0.0190(10) 0.0159(10) 0.0148(9) 0.0004(8) 0.0056(8) 0.0008(8) N3 0.0225(10) 0.0177(10) 0.0169(10) 0.0004(8) 0.0085(8) -0.0011(8) C1 0.0207(12) 0.0173(12) 0.0148(11) 0.0060(9) 0.0040(9) -0.0025(10) C2 0.0202(12) 0.0157(11) 0.0151(11) 0.0050(9) 0.0050(9) -0.0001(9) C3 0.0223(13) 0.0206(13) 0.0189(12) 0.0043(9) 0.0035(10) -0.0027(10) C4 0.0147(11) 0.0264(13) 0.0237(12) 0.0085(10) 0.0038(10) -0.0009(10) C5 0.0267(13) 0.0190(12) 0.0205(12) 0.0084(10) 0.0107(10) 0.0021(10) C6 0.0255(13) 0.0173(12) 0.0207(12) 0.0067(10) 0.0088(10) 0.0011(10) C7 0.0338(15) 0.0196(13) 0.0254(13) -0.0012(10) 0.0127(11) 0.0016(11) C8 0.0335(15) 0.0232(13) 0.0278(14) -0.0069(11) 0.0101(11) -0.0046(11) C9 0.0269(13) 0.0207(13) 0.0235(13) -0.0001(10) 0.0075(10) -0.0055(10) C10 0.0228(12) 0.0145(11) 0.0159(11) 0.0030(9) 0.0059(9) -0.0024(9) C11 0.0233(12) 0.0133(11) 0.0153(11) 0.0061(9) 0.0055(9) 0.0001(9) C12 0.0208(12) 0.0148(11) 0.0161(11) 0.0044(9) 0.0045(9) -0.0009(9) C13 0.0199(12) 0.0197(12) 0.0178(12) -0.0004(9) 0.0057(9) 0.0039(10) C14 0.0200(12) 0.0269(14) 0.0210(12) -0.0012(10) 0.0059(10) -0.0011(10) C15 0.0358(14) 0.0146(12) 0.0219(12) 0.0007(10) 0.0113(11) 0.0037(11) C16 0.0338(15) 0.0312(15) 0.0239(13) 0.0057(11) 0.0096(11) 0.0087(12) C17 0.0271(14) 0.0447(17) 0.0203(13) -0.0022(12) 0.0066(11) -0.0035(13) C18 0.0383(15) 0.0280(14) 0.0223(13) -0.0078(11) 0.0120(11) -0.0096(12) C19 0.0321(14) 0.0171(12) 0.0231(13) -0.0028(10) 0.0119(11) 0.0005(10) P1 0.0261(4) 0.0158(4) 0.0279(4) 0.0021(2) 0.0089(3) 0.0002(3) F1 0.0331(8) 0.0169(8) 0.0293(8) 0.0004(6) 0.0083(6) -0.0038(6) F2 0.0386(10) 0.0311(10) 0.0791(15) 0.0166(9) 0.0192(10) -0.0073(8) F3 0.0635(15) 0.0342(12) 0.150(3) 0.0126(13) 0.0709(16) 0.0152(10) F4 0.0726(16) 0.0654(15) 0.0471(12) 0.0132(11) -0.0209(11) -0.0340(13) F5 0.0493(12) 0.0188(9) 0.0919(16) -0.0040(9) 0.0314(11) 0.0013(8) F6 0.1002(19) 0.0690(16) 0.0256(10) 0.0092(10) 0.0039(11) -0.0311(14) _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 O1 C12 1.222(3) . ? O2 C1 1.233(3) . ? N1 C5 1.350(3) . ? N1 H1X 0.9128 . ? N1 H1Y 0.9658 . ? N2 C12 1.397(3) . ? N2 C1 1.412(3) . ? N2 C13 1.470(3) . ? N3 C19 1.350(3) . ? N3 C15 1.353(3) . ? N3 C14 1.491(3) . ? C1 C2 1.442(3) . ? C2 C3 1.390(3) . ? C2 C11 1.428(3) . ? C3 C4 1.390(4) . ? C3 H3 0.9500 . ? C4 C5 1.407(4) . ? C4 H4 0.9500 . ? C5 C6 1.437(4) . ? C6 C11 1.421(3) . ? C6 C7 1.421(4) . ? C7 C8 1.367(4) . ? C7 H7 0.9500 . ? C8 C9 1.396(4) . ? C8 H8 0.9500 . ? C9 C10 1.385(4) . ? C9 H9 0.9500 . ? C10 C11 1.418(3) . ? C10 C12 1.467(3) . ? C13 C14 1.526(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.378(4) . ? C15 H15 0.9500 . ? C16 C17 1.388(4) . ? C16 H16 0.9500 . ? C17 C18 1.374(4) . ? C17 H17 0.9500 . ? C18 C19 1.373(4) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? P1 F3 1.574(2) . ? P1 F4 1.583(2) . ? P1 F6 1.591(2) . ? P1 F5 1.5977(19) . ? P1 F2 1.6008(18) . ? P1 F1 1.6067(16) . ? 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 C5 N1 H1X 120.1 . . ? C5 N1 H1Y 120.5 . . ? H1X N1 H1Y 119.4 . . ? C12 N2 C1 125.0(2) . . ? C12 N2 C13 116.9(2) . . ? C1 N2 C13 118.1(2) . . ? C19 N3 C15 121.0(2) . . ? C19 N3 C14 118.7(2) . . ? C15 N3 C14 120.1(2) . . ? O2 C1 N2 119.1(2) . . ? O2 C1 C2 124.0(2) . . ? N2 C1 C2 116.8(2) . . ? C3 C2 C11 118.7(2) . . ? C3 C2 C1 120.5(2) . . ? C11 C2 C1 120.8(2) . . ? C2 C3 C4 121.2(2) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 121.6(2) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? N1 C5 C4 120.3(2) . . ? N1 C5 C6 121.0(2) . . ? C4 C5 C6 118.7(2) . . ? C11 C6 C7 118.1(2) . . ? C11 C6 C5 118.7(2) . . ? C7 C6 C5 123.3(2) . . ? C8 C7 C6 122.0(2) . . ? C8 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? C7 C8 C9 120.0(3) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 121.0(2) . . ? C9 C10 C12 119.0(2) . . ? C11 C10 C12 120.0(2) . . ? C10 C11 C6 118.9(2) . . ? C10 C11 C2 120.1(2) . . ? C6 C11 C2 121.0(2) . . ? O1 C12 N2 119.9(2) . . ? O1 C12 C10 123.0(2) . . ? N2 C12 C10 117.1(2) . . ? N2 C13 C14 112.7(2) . . ? N2 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? N2 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? N3 C14 C13 110.2(2) . . ? N3 C14 H14A 109.6 . . ? C13 C14 H14A 109.6 . . ? N3 C14 H14B 109.6 . . ? C13 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? N3 C15 C16 120.3(2) . . ? N3 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C17 118.9(3) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C18 C17 C16 119.9(3) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C19 C18 C17 119.4(3) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? N3 C19 C18 120.4(2) . . ? N3 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? F3 P1 F4 91.22(17) . . ? F3 P1 F6 91.23(17) . . ? F4 P1 F6 177.50(16) . . ? F3 P1 F5 179.14(12) . . ? F4 P1 F5 88.92(15) . . ? F6 P1 F5 88.63(14) . . ? F3 P1 F2 90.61(12) . . ? F4 P1 F2 91.10(12) . . ? F6 P1 F2 89.40(12) . . ? F5 P1 F2 90.24(11) . . ? F3 P1 F1 89.82(10) . . ? F4 P1 F1 89.90(10) . . ? F6 P1 F1 89.58(10) . . ? F5 P1 F1 89.32(9) . . ? F2 P1 F1 178.90(11) . . ? 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 C12 N2 C1 O2 179.0(2) . . . . ? C13 N2 C1 O2 2.4(3) . . . . ? C12 N2 C1 C2 -1.8(3) . . . . ? C13 N2 C1 C2 -178.40(19) . . . . ? O2 C1 C2 C3 0.9(4) . . . . ? N2 C1 C2 C3 -178.2(2) . . . . ? O2 C1 C2 C11 -177.0(2) . . . . ? N2 C1 C2 C11 3.8(3) . . . . ? C11 C2 C3 C4 -0.5(3) . . . . ? C1 C2 C3 C4 -178.5(2) . . . . ? C2 C3 C4 C5 2.0(4) . . . . ? C3 C4 C5 N1 178.4(2) . . . . ? C3 C4 C5 C6 -1.2(4) . . . . ? N1 C5 C6 C11 179.4(2) . . . . ? C4 C5 C6 C11 -1.0(3) . . . . ? N1 C5 C6 C7 -1.7(4) . . . . ? C4 C5 C6 C7 178.0(2) . . . . ? C11 C6 C7 C8 -1.8(4) . . . . ? C5 C6 C7 C8 179.3(2) . . . . ? C6 C7 C8 C9 -0.3(4) . . . . ? C7 C8 C9 C10 1.9(4) . . . . ? C8 C9 C10 C11 -1.3(4) . . . . ? C8 C9 C10 C12 177.6(2) . . . . ? C9 C10 C11 C6 -0.7(3) . . . . ? C12 C10 C11 C6 -179.7(2) . . . . ? C9 C10 C11 C2 178.0(2) . . . . ? C12 C10 C11 C2 -0.9(3) . . . . ? C7 C6 C11 C10 2.2(3) . . . . ? C5 C6 C11 C10 -178.8(2) . . . . ? C7 C6 C11 C2 -176.6(2) . . . . ? C5 C6 C11 C2 2.5(3) . . . . ? C3 C2 C11 C10 179.5(2) . . . . ? C1 C2 C11 C10 -2.5(3) . . . . ? C3 C2 C11 C6 -1.7(3) . . . . ? C1 C2 C11 C6 176.2(2) . . . . ? C1 N2 C12 O1 179.4(2) . . . . ? C13 N2 C12 O1 -4.0(3) . . . . ? C1 N2 C12 C10 -1.4(3) . . . . ? C13 N2 C12 C10 175.16(19) . . . . ? C9 C10 C12 O1 3.0(4) . . . . ? C11 C10 C12 O1 -178.1(2) . . . . ? C9 C10 C12 N2 -176.2(2) . . . . ? C11 C10 C12 N2 2.8(3) . . . . ? C12 N2 C13 C14 89.4(2) . . . . ? C1 N2 C13 C14 -93.8(3) . . . . ? C19 N3 C14 C13 72.9(3) . . . . ? C15 N3 C14 C13 -101.2(3) . . . . ? N2 C13 C14 N3 67.0(3) . . . . ? C19 N3 C15 C16 -0.7(4) . . . . ? C14 N3 C15 C16 173.3(2) . . . . ? N3 C15 C16 C17 -1.0(4) . . . . ? C15 C16 C17 C18 2.2(4) . . . . ? C16 C17 C18 C19 -1.9(4) . . . . ? C15 N3 C19 C18 1.0(4) . . . . ? C14 N3 C19 C18 -173.1(2) . . . . ? C17 C18 C19 N3 0.3(4) . . . . ? 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 H1X O1 0.91 2.07 2.919(3) 154.1 1_655 N1 H1Y F5 0.97 2.52 3.304(3) 138.7 3_665 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.721 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.081