# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Severin, Kay' 'Lee, Boram' 'copelliti, Rosario' _publ_contact_author_name 'Dr Kay Severin' _publ_contact_author_email kay.severin@epfl.ch _publ_section_title ; A molecular probe for the optical detection of biogenic amines ; # Attachment '- coumarin C2.cif' data_bo01 _database_code_depnum_ccdc_archive 'CCDC 824329' #TrackingRef '- coumarin C2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H29 N3 O2' _chemical_formula_sum 'C20 H29 N3 O2' _chemical_formula_weight 343.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P n' _symmetry_space_group_name_Hall 'P -2yac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 5.0310(10) _cell_length_b 12.153(2) _cell_length_c 15.766(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.05(3) _cell_angle_gamma 90.00 _cell_volume 960.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 83 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(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 marmux _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3154 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.1039 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3149 _reflns_number_gt 2268 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'marmux - Micro-beam system, marresearch, 2010' _computing_cell_refinement 'automar, marresearch, 2010' _computing_data_reduction 'automar, marresearch, 2010' _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^)+(0.1243P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.40(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(2) _refine_ls_number_reflns 3149 _refine_ls_number_parameters 231 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0910 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.1874 _refine_ls_wR_factor_gt 0.1650 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _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 0.7138(5) 0.51310(19) 0.63221(16) 0.0562(7) Uani 1 1 d . . . O2 O 0.6028(5) 0.4012(2) 0.73220(17) 0.0630(7) Uani 1 1 d . . . N1 N -0.0120(6) 0.2532(2) 0.5924(2) 0.0559(8) Uani 1 1 d . . . N2 N 0.1223(6) 0.3770(3) 0.4629(2) 0.0556(8) Uani 1 1 d . . . H2 H 0.030(12) 0.309(4) 0.493(4) 0.105(17) Uiso 1 1 d . . . N3 N 0.9912(6) 0.7826(3) 0.4439(2) 0.0630(8) Uani 1 1 d . . . C1 C 0.5492(7) 0.4317(3) 0.6588(3) 0.0573(9) Uani 1 1 d . . . C2 C 0.3410(7) 0.3901(3) 0.5999(2) 0.0526(9) Uani 1 1 d . . . C3 C 0.3079(7) 0.4272(3) 0.5151(2) 0.0500(8) Uani 1 1 d . . . C4 C 0.4780(6) 0.5175(3) 0.4907(2) 0.0495(8) Uani 1 1 d . . . C5 C 0.6750(7) 0.5568(3) 0.5510(2) 0.0513(8) Uani 1 1 d . . . C6 C 0.4618(7) 0.5740(3) 0.4122(3) 0.0554(9) Uani 1 1 d . . . H6 H 0.3294 0.5522 0.3688 0.067 Uiso 1 1 calc R . . C7 C 0.6294(7) 0.6592(3) 0.3960(2) 0.0537(9) Uani 1 1 d . . . H7 H 0.6112 0.6938 0.3418 0.064 Uiso 1 1 calc R . . C8 C 0.8273(7) 0.6963(3) 0.4579(2) 0.0531(9) Uani 1 1 d . . . C9 C 0.8465(7) 0.6421(3) 0.5370(2) 0.0516(8) Uani 1 1 d . . . H9 H 0.9774 0.6642 0.5808 0.062 Uiso 1 1 calc R . . C10 C 0.1754(8) 0.3068(3) 0.6344(3) 0.0559(9) Uani 1 1 d . . . H10 H 0.2086 0.2905 0.6933 0.067 Uiso 1 1 calc R . . C11 C -0.1563(8) 0.1724(3) 0.6400(3) 0.0606(10) Uani 1 1 d . . . H11A H -0.3365 0.2011 0.6479 0.073 Uiso 1 1 calc R . . H11B H -0.0608 0.1620 0.6971 0.073 Uiso 1 1 calc R . . C12 C -0.1823(9) 0.0633(3) 0.5954(3) 0.0660(11) Uani 1 1 d . . . H12 H -0.0008 0.0392 0.5817 0.079 Uiso 1 1 calc R . . C13 C -0.2937(11) -0.0234(4) 0.6524(3) 0.0808(13) Uani 1 1 d . . . H13A H -0.1716 -0.0330 0.7038 0.121 Uiso 1 1 calc R . . H13B H -0.3128 -0.0934 0.6215 0.121 Uiso 1 1 calc R . . H13C H -0.4685 0.0004 0.6684 0.121 Uiso 1 1 calc R . . C14 C -0.3601(13) 0.0729(5) 0.5124(4) 0.1009(18) Uani 1 1 d . . . H14A H -0.5455 0.0839 0.5251 0.151 Uiso 1 1 calc R . . H14B H -0.3469 0.0054 0.4791 0.151 Uiso 1 1 calc R . . H14C H -0.3023 0.1357 0.4797 0.151 Uiso 1 1 calc R . . C15 C 0.0427(8) 0.3928(3) 0.3715(2) 0.0568(9) Uani 1 1 d . . . H15A H 0.2036 0.3958 0.3396 0.068 Uiso 1 1 calc R . . H15B H -0.0543 0.4633 0.3627 0.068 Uiso 1 1 calc R . . C16 C -0.1342(8) 0.2990(3) 0.3387(3) 0.0599(10) Uani 1 1 d . . . H16 H -0.2820 0.2917 0.3768 0.072 Uiso 1 1 calc R . . C17 C 0.0163(11) 0.1904(4) 0.3403(4) 0.0770(12) Uani 1 1 d . . . H17A H 0.1606 0.1951 0.3026 0.115 Uiso 1 1 calc R . . H17B H -0.1065 0.1311 0.3208 0.115 Uiso 1 1 calc R . . H17C H 0.0916 0.1748 0.3985 0.115 Uiso 1 1 calc R . . C18 C -0.2573(10) 0.3259(4) 0.2499(3) 0.0776(12) Uani 1 1 d . . . H18A H -0.3576 0.3950 0.2513 0.116 Uiso 1 1 calc R . . H18B H -0.3780 0.2664 0.2296 0.116 Uiso 1 1 calc R . . H18C H -0.1158 0.3339 0.2114 0.116 Uiso 1 1 calc R . . C19 C 0.9886(9) 0.8312(3) 0.3596(3) 0.0681(11) Uani 1 1 d . . . H19A H 1.0218 0.7739 0.3181 0.102 Uiso 1 1 calc R . . H19B H 1.1280 0.8875 0.3597 0.102 Uiso 1 1 calc R . . H19C H 0.8141 0.8649 0.3442 0.102 Uiso 1 1 calc R . . C20 C 1.1947(8) 0.8163(3) 0.5100(3) 0.0644(11) Uani 1 1 d . . . H20A H 1.1115 0.8312 0.5627 0.097 Uiso 1 1 calc R . . H20B H 1.2831 0.8831 0.4918 0.097 Uiso 1 1 calc R . . H20C H 1.3268 0.7574 0.5199 0.097 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 O1 0.0625(15) 0.0509(14) 0.0532(15) 0.0035(11) -0.0066(11) -0.0063(11) O2 0.0735(17) 0.0601(15) 0.0532(17) 0.0028(13) -0.0065(13) -0.0029(13) N1 0.0601(18) 0.0511(16) 0.0569(19) 0.0021(13) 0.0068(15) -0.0034(14) N2 0.0588(17) 0.0541(17) 0.0529(18) -0.0008(14) -0.0006(13) -0.0031(14) N3 0.0672(19) 0.0592(18) 0.062(2) 0.0001(16) -0.0003(15) -0.0126(16) C1 0.060(2) 0.0425(18) 0.068(3) 0.0025(18) -0.0033(18) -0.0002(16) C2 0.0535(19) 0.0494(18) 0.054(2) -0.0016(17) 0.0000(16) 0.0013(15) C3 0.0510(18) 0.0424(18) 0.055(2) 0.0034(15) -0.0033(15) 0.0036(14) C4 0.0497(19) 0.0469(18) 0.051(2) -0.0002(15) 0.0003(15) 0.0025(15) C5 0.059(2) 0.0442(18) 0.049(2) 0.0023(15) -0.0021(15) 0.0061(15) C6 0.0560(19) 0.051(2) 0.058(2) -0.0005(16) -0.0049(16) 0.0019(17) C7 0.056(2) 0.0530(19) 0.051(2) 0.0017(16) 0.0007(16) -0.0027(16) C8 0.057(2) 0.0435(18) 0.059(2) -0.0029(16) 0.0065(16) -0.0007(15) C9 0.0526(18) 0.0467(18) 0.054(2) -0.0029(16) -0.0038(15) 0.0009(15) C10 0.060(2) 0.051(2) 0.057(2) 0.0004(17) 0.0040(17) -0.0007(17) C11 0.066(2) 0.056(2) 0.060(2) 0.0041(18) 0.0072(18) -0.0106(17) C12 0.068(2) 0.051(2) 0.080(3) 0.0014(19) 0.015(2) -0.0062(17) C13 0.088(3) 0.058(2) 0.096(4) 0.015(2) 0.006(3) -0.012(2) C14 0.124(4) 0.103(4) 0.077(4) -0.007(3) 0.013(3) -0.054(3) C15 0.064(2) 0.0518(19) 0.053(2) 0.0034(17) -0.0042(17) -0.0031(17) C16 0.064(2) 0.059(2) 0.055(2) -0.0012(17) -0.0022(18) -0.0085(17) C17 0.087(3) 0.060(2) 0.083(3) -0.012(2) 0.005(2) -0.009(2) C18 0.080(3) 0.089(3) 0.059(3) 0.006(2) -0.015(2) -0.024(2) C19 0.080(3) 0.061(2) 0.063(3) 0.006(2) -0.001(2) -0.015(2) C20 0.063(2) 0.056(2) 0.073(3) -0.0051(18) -0.002(2) -0.0143(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 O1 C1 1.379(4) . ? O1 C5 1.385(4) . ? O2 C1 1.222(5) . ? N1 C10 1.281(5) . ? N1 C11 1.467(5) . ? N2 C3 1.336(5) . ? N2 C15 1.474(5) . ? N2 H2 1.08(6) . ? N3 C8 1.365(5) . ? N3 C19 1.453(5) . ? N3 C20 1.454(5) . ? C1 C2 1.430(5) . ? C2 C3 1.407(5) . ? C2 C10 1.447(5) . ? C3 C4 1.463(5) . ? C4 C5 1.396(5) . ? C4 C6 1.411(5) . ? C5 C9 1.378(5) . ? C6 C7 1.374(5) . ? C6 H6 0.9500 . ? C7 C8 1.406(5) . ? C7 H7 0.9500 . ? C8 C9 1.406(5) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.501(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.523(6) . ? C12 C14 1.523(8) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.509(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C18 1.517(6) . ? C16 C17 1.521(6) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 O1 C5 121.2(3) . . ? C10 N1 C11 116.8(3) . . ? C3 N2 C15 131.1(3) . . ? C3 N2 H2 113(3) . . ? C15 N2 H2 116(3) . . ? C8 N3 C19 120.3(3) . . ? C8 N3 C20 119.9(3) . . ? C19 N3 C20 119.3(3) . . ? O2 C1 O1 114.7(3) . . ? O2 C1 C2 126.6(4) . . ? O1 C1 C2 118.7(3) . . ? C3 C2 C1 121.6(3) . . ? C3 C2 C10 123.9(3) . . ? C1 C2 C10 114.6(3) . . ? N2 C3 C2 117.1(3) . . ? N2 C3 C4 125.0(3) . . ? C2 C3 C4 117.8(3) . . ? C5 C4 C6 114.4(3) . . ? C5 C4 C3 118.3(3) . . ? C6 C4 C3 127.3(3) . . ? C9 C5 O1 113.4(3) . . ? C9 C5 C4 124.5(3) . . ? O1 C5 C4 122.1(3) . . ? C7 C6 C4 122.8(3) . . ? C7 C6 H6 118.6 . . ? C4 C6 H6 118.6 . . ? C6 C7 C8 121.4(3) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? N3 C8 C9 120.6(3) . . ? N3 C8 C7 122.3(3) . . ? C9 C8 C7 117.1(3) . . ? C5 C9 C8 119.9(3) . . ? C5 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? N1 C10 C2 125.7(4) . . ? N1 C10 H10 117.2 . . ? C2 C10 H10 117.2 . . ? N1 C11 C12 112.3(3) . . ? N1 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? N1 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C13 110.9(4) . . ? C11 C12 C14 110.8(4) . . ? C13 C12 C14 109.9(4) . . ? C11 C12 H12 108.4 . . ? C13 C12 H12 108.4 . . ? C14 C12 H12 108.4 . . ? 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 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 C16 109.7(3) . . ? N2 C15 H15A 109.7 . . ? C16 C15 H15A 109.7 . . ? N2 C15 H15B 109.7 . . ? C16 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C15 C16 C18 109.5(3) . . ? C15 C16 C17 111.9(3) . . ? C18 C16 C17 111.4(4) . . ? C15 C16 H16 108.0 . . ? C18 C16 H16 108.0 . . ? C17 C16 H16 108.0 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 H19A 109.5 . . ? N3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 O1 C1 O2 -179.2(3) . . . . ? C5 O1 C1 C2 2.0(5) . . . . ? O2 C1 C2 C3 -176.1(3) . . . . ? O1 C1 C2 C3 2.5(5) . . . . ? O2 C1 C2 C10 2.7(5) . . . . ? O1 C1 C2 C10 -178.6(3) . . . . ? C15 N2 C3 C2 -178.0(3) . . . . ? C15 N2 C3 C4 2.1(6) . . . . ? C1 C2 C3 N2 174.6(3) . . . . ? C10 C2 C3 N2 -4.2(5) . . . . ? C1 C2 C3 C4 -5.6(5) . . . . ? C10 C2 C3 C4 175.7(3) . . . . ? N2 C3 C4 C5 -175.9(3) . . . . ? C2 C3 C4 C5 4.2(5) . . . . ? N2 C3 C4 C6 6.4(6) . . . . ? C2 C3 C4 C6 -173.5(3) . . . . ? C1 O1 C5 C9 176.0(3) . . . . ? C1 O1 C5 C4 -3.3(5) . . . . ? C6 C4 C5 C9 -1.2(5) . . . . ? C3 C4 C5 C9 -179.1(3) . . . . ? C6 C4 C5 O1 178.1(3) . . . . ? C3 C4 C5 O1 0.1(5) . . . . ? C5 C4 C6 C7 1.2(5) . . . . ? C3 C4 C6 C7 179.0(3) . . . . ? C4 C6 C7 C8 -0.8(5) . . . . ? C19 N3 C8 C9 173.9(4) . . . . ? C20 N3 C8 C9 2.4(5) . . . . ? C19 N3 C8 C7 -7.7(5) . . . . ? C20 N3 C8 C7 -179.2(4) . . . . ? C6 C7 C8 N3 -178.3(3) . . . . ? C6 C7 C8 C9 0.2(5) . . . . ? O1 C5 C9 C8 -178.7(3) . . . . ? C4 C5 C9 C8 0.7(5) . . . . ? N3 C8 C9 C5 178.4(3) . . . . ? C7 C8 C9 C5 -0.1(5) . . . . ? C11 N1 C10 C2 -179.8(3) . . . . ? C3 C2 C10 N1 3.2(6) . . . . ? C1 C2 C10 N1 -175.6(4) . . . . ? C10 N1 C11 C12 -131.7(4) . . . . ? N1 C11 C12 C13 171.2(4) . . . . ? N1 C11 C12 C14 -66.5(5) . . . . ? C3 N2 C15 C16 167.5(3) . . . . ? N2 C15 C16 C18 169.4(3) . . . . ? N2 C15 C16 C17 -66.7(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 N2 H2 N1 1.08(6) 1.74(6) 2.670(5) 141(5) . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.308 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.065