# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Trinchera, Piera' 'Musio, Biagia' 'Degennaro, Leonardo' 'Moliterni, Anna' 'Falcicchio, Aurelia' 'LUISI, RENZO' _publ_contact_author_name 'LUISI, RENZO' _publ_contact_author_email luisi@farmchim.uniba.it _publ_section_title ; One-pot Preparation of Piperazines by Regioselective Ring-Opening of Non-Activated Arylaziridines ; # Attachment '- fileunico_pt263_pt43_pt231.cif' data_meso_2n _database_code_depnum_ccdc_archive 'CCDC 859214' #TrackingRef '- fileunico_pt263_pt43_pt231.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H30 N2' _chemical_formula_sum 'C24 H30 N2' _chemical_formula_weight 346.50 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 8.4011(7) _cell_length_b 10.0557(8) _cell_length_c 13.0329(15) _cell_angle_alpha 74.541(7) _cell_angle_beta 78.907(7) _cell_angle_gamma 76.897(6) _cell_volume 1023.28(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 5.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.125 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9744 _exptl_absorpt_correction_T_max 0.9871 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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-Nonius KappaCCD' _diffrn_measurement_method '\f scans 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 12358 _diffrn_reflns_av_R_equivalents 0.0734 _diffrn_reflns_av_sigmaI/netI 0.0898 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.03 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4612 _reflns_number_gt 2354 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2002) ' _computing_cell_refinement 'DIRAX (Duisenberg,1992)' _computing_data_reduction 'EVAL (Nonius, 2002)' _computing_structure_solution 'SIR2011, updated version of SIR2008 (Burla et al., 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0663P)^2^+0.0245P] 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 4612 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1402 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1511 _refine_ls_wR_factor_gt 0.1212 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 0.46607(19) 1.62091(16) 0.04583(13) 0.0382(4) Uani 1 1 d . . . N2 N 0.0458(2) 0.87990(16) 0.45306(13) 0.0401(4) Uani 1 1 d . . . C3 C 0.6722(2) 1.4975(2) 0.17047(15) 0.0377(5) Uani 1 1 d . . . C6 C 0.2647(2) 0.9898(2) 0.32667(15) 0.0388(5) Uani 1 1 d . . . C7 C 0.3865(3) 0.8771(2) 0.36282(18) 0.0491(5) Uani 1 1 d . . . H7 H 0.3625 0.8147 0.4281 0.059 Uiso 1 1 calc R . . C8 C 0.3026(3) 1.0846(2) 0.22918(16) 0.0438(5) Uani 1 1 d . . . C9 C 0.7666(2) 1.6008(2) 0.12993(17) 0.0463(5) Uani 1 1 d . . . H9 H 0.7488 1.6641 0.0649 0.056 Uiso 1 1 calc R . . C10 C 0.6989(2) 1.4035(2) 0.26859(16) 0.0423(5) Uani 1 1 d . . . C11 C 0.3662(3) 1.7035(2) 0.11976(19) 0.0555(6) Uani 1 1 d . . . H11A H 0.4355 1.7197 0.1641 0.083 Uiso 1 1 calc R . . H11B H 0.2835 1.6534 0.1643 0.083 Uiso 1 1 calc R . . H11C H 0.3138 1.7919 0.0796 0.083 Uiso 1 1 calc R . . C12 C 0.9128(3) 1.5201(3) 0.2814(2) 0.0559(6) Uani 1 1 d . . . H12 H 0.9927 1.5279 0.3188 0.067 Uiso 1 1 calc R . . C13 C 0.8874(3) 1.6117(2) 0.1844(2) 0.0544(6) Uani 1 1 d . . . H13 H 0.9511 1.6809 0.1555 0.065 Uiso 1 1 calc R . . C14 C 0.8200(3) 1.4172(2) 0.32276(18) 0.0513(6) Uani 1 1 d . . . H14 H 0.8382 1.3552 0.3883 0.062 Uiso 1 1 calc R . . C15 C 0.1823(3) 1.2149(2) 0.18594(19) 0.0594(6) Uani 1 1 d . . . H15A H 0.1248 1.2547 0.2460 0.071 Uiso 1 1 calc R . . H15B H 0.2455 1.2827 0.1387 0.071 Uiso 1 1 calc R . . C16 C 0.6055(3) 1.2855(2) 0.31835(19) 0.0618(7) Uani 1 1 d . . . H16A H 0.5829 1.2503 0.2612 0.074 Uiso 1 1 calc R . . H16B H 0.6757 1.2096 0.3615 0.074 Uiso 1 1 calc R . . C17 C 0.5407(3) 0.8550(3) 0.3053(2) 0.0579(6) Uani 1 1 d . . . H17 H 0.6205 0.7791 0.3314 0.069 Uiso 1 1 calc R . . C18 C 0.4592(3) 1.0593(2) 0.17146(18) 0.0543(6) Uani 1 1 d . . . H18 H 0.4851 1.1205 0.1059 0.065 Uiso 1 1 calc R . . C20 C 0.5761(3) 0.9463(3) 0.2087(2) 0.0611(7) Uani 1 1 d . . . H20 H 0.6798 0.9315 0.1684 0.073 Uiso 1 1 calc R . . C19 C 0.0225(3) 0.8007(2) 0.3800(2) 0.0613(7) Uani 1 1 d . . . H19A H 0.1248 0.7789 0.3349 0.092 Uiso 1 1 calc R . . H19B H -0.0598 0.8559 0.3361 0.092 Uiso 1 1 calc R . . H19C H -0.0129 0.7152 0.4209 0.092 Uiso 1 1 calc R . . C1 C 0.5482(2) 1.4839(2) 0.10376(16) 0.0366(5) Uani 1 1 d . . . H1A H 0.462(2) 1.4316(19) 0.1545(16) 0.044 Uiso 1 1 d . . . C4 C 0.3593(2) 1.5994(2) -0.02258(17) 0.0394(5) Uani 1 1 d . . . H4B H 0.268(2) 1.549(2) 0.0244(16) 0.047 Uiso 1 1 d . . . H4A H 0.305(2) 1.695(2) -0.0583(16) 0.047 Uiso 1 1 d . . . C23 C 0.0406(5) 1.0882(4) 0.1048(3) 0.0932(11) Uani 1 1 d . . . H23A H -0.045(4) 1.090(3) 0.065(3) 0.112 Uiso 1 1 d . . . H23B H 0.111(4) 1.005(3) 0.128(3) 0.112 Uiso 1 1 d . . . C5 C 0.0984(2) 1.0123(2) 0.39548(16) 0.0367(5) Uani 1 1 d . . . H5A H 0.011(2) 1.071(2) 0.3503(15) 0.044 Uiso 1 1 d . . . C2 C -0.1092(3) 0.9086(2) 0.52314(17) 0.0410(5) Uani 1 1 d . . . H2A H -0.198(3) 0.966(2) 0.4777(16) 0.049 Uiso 1 1 d . . . H2B H -0.140(2) 0.817(2) 0.5618(16) 0.049 Uiso 1 1 d . . . C22 C 0.4482(4) 1.3227(5) 0.3865(3) 0.0819(9) Uani 1 1 d . . . H22A H 0.391(4) 1.239(3) 0.422(2) 0.098 Uiso 1 1 d . . . C21 C 0.0573(3) 1.1993(4) 0.1268(2) 0.0722(8) Uani 1 1 d . . . H21A H -0.027(3) 1.297(3) 0.096(2) 0.087 Uiso 1 1 d . . . C24 C 0.3823(5) 1.4421(5) 0.4074(3) 0.1020(12) Uani 1 1 d . . . H24A H 0.283(5) 1.461(3) 0.453(3) 0.122 Uiso 1 1 d . . . H24B H 0.438(4) 1.520(4) 0.379(3) 0.122 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 0.0384(9) 0.0416(9) 0.0380(9) -0.0137(7) -0.0114(7) -0.0040(7) N2 0.0439(10) 0.0402(9) 0.0398(9) -0.0143(8) 0.0011(8) -0.0146(8) C3 0.0353(11) 0.0447(11) 0.0359(10) -0.0138(9) -0.0066(9) -0.0068(9) C6 0.0364(11) 0.0457(12) 0.0369(11) -0.0144(9) -0.0035(9) -0.0090(9) C7 0.0418(12) 0.0577(14) 0.0456(12) -0.0118(11) -0.0035(10) -0.0075(11) C8 0.0468(12) 0.0470(12) 0.0400(11) -0.0122(10) -0.0010(10) -0.0152(10) C9 0.0413(12) 0.0567(13) 0.0419(12) -0.0095(10) -0.0073(10) -0.0124(10) C10 0.0452(12) 0.0467(12) 0.0367(11) -0.0114(9) -0.0086(9) -0.0073(10) C11 0.0524(13) 0.0626(14) 0.0584(14) -0.0304(12) -0.0169(11) 0.0023(11) C12 0.0456(13) 0.0683(16) 0.0663(16) -0.0313(13) -0.0248(12) -0.0033(12) C13 0.0418(13) 0.0639(15) 0.0649(15) -0.0240(12) -0.0073(11) -0.0143(11) C14 0.0544(14) 0.0560(13) 0.0467(13) -0.0154(11) -0.0230(11) 0.0011(11) C15 0.0638(15) 0.0558(14) 0.0486(13) 0.0009(11) 0.0006(12) -0.0135(12) C16 0.0781(18) 0.0603(15) 0.0505(14) 0.0016(12) -0.0279(14) -0.0210(14) C17 0.0396(13) 0.0651(15) 0.0683(16) -0.0218(13) -0.0059(12) -0.0025(11) C18 0.0537(14) 0.0609(14) 0.0473(13) -0.0135(11) 0.0118(11) -0.0237(12) C20 0.0396(13) 0.0751(17) 0.0717(17) -0.0305(14) 0.0118(12) -0.0174(12) C19 0.0665(16) 0.0668(15) 0.0642(15) -0.0361(13) 0.0058(12) -0.0278(13) C1 0.0381(11) 0.0408(11) 0.0318(10) -0.0061(8) -0.0085(9) -0.0088(9) C4 0.0378(11) 0.0422(11) 0.0403(11) -0.0104(9) -0.0130(10) -0.0044(10) C23 0.107(3) 0.093(2) 0.089(2) -0.033(2) -0.042(2) -0.001(2) C5 0.0355(11) 0.0396(11) 0.0350(10) -0.0078(9) -0.0036(9) -0.0090(9) C2 0.0406(12) 0.0421(12) 0.0420(12) -0.0111(10) 0.0007(10) -0.0146(10) C22 0.068(2) 0.106(3) 0.0698(19) 0.0068(19) -0.0131(16) -0.0404(19) C21 0.0637(17) 0.084(2) 0.0589(16) -0.0070(15) -0.0067(13) -0.0055(15) C24 0.073(2) 0.142(4) 0.079(2) -0.020(2) 0.0074(17) -0.016(2) _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 C11 1.457(3) . ? N1 C4 1.465(2) . ? N1 C1 1.469(2) . ? N2 C2 1.458(2) . ? N2 C19 1.458(2) . ? N2 C5 1.462(2) . ? C3 C9 1.381(3) . ? C3 C10 1.396(3) . ? C3 C1 1.528(2) . ? C6 C7 1.389(3) . ? C6 C8 1.400(3) . ? C6 C5 1.514(3) . ? C7 C17 1.369(3) . ? C7 H7 0.9300 . ? C8 C18 1.389(3) . ? C8 C15 1.510(3) . ? C9 C13 1.383(3) . ? C9 H9 0.9300 . ? C10 C14 1.395(3) . ? C10 C16 1.504(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C14 1.369(3) . ? C12 C13 1.373(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C21 1.474(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C22 1.475(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C20 1.371(3) . ? C17 H17 0.9300 . ? C18 C20 1.369(3) . ? C18 H18 0.9300 . ? C20 H20 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C1 C4 1.512(3) 2_685 ? C1 H1A 1.02(2) . ? C4 C1 1.512(3) 2_685 ? C4 H4B 1.02(2) . ? C4 H4A 0.99(2) . ? C23 C21 1.267(4) . ? C23 H23A 0.96(3) . ? C23 H23B 0.92(3) . ? C5 C2 1.512(3) 2_576 ? C5 H5A 1.012(19) . ? C2 C5 1.512(3) 2_576 ? C2 H2A 1.01(2) . ? C2 H2B 0.99(2) . ? C22 C24 1.280(5) . ? C22 H22A 1.02(3) . ? C21 H21A 1.10(3) . ? C24 H24A 0.94(4) . ? C24 H24B 0.95(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 C11 N1 C4 108.84(15) . . ? C11 N1 C1 111.50(15) . . ? C4 N1 C1 109.34(14) . . ? C2 N2 C19 108.80(16) . . ? C2 N2 C5 109.40(15) . . ? C19 N2 C5 112.11(16) . . ? C9 C3 C10 119.07(17) . . ? C9 C3 C1 119.13(17) . . ? C10 C3 C1 121.70(17) . . ? C7 C6 C8 118.64(19) . . ? C7 C6 C5 119.80(18) . . ? C8 C6 C5 121.47(18) . . ? C17 C7 C6 122.0(2) . . ? C17 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? C18 C8 C6 118.4(2) . . ? C18 C8 C15 118.8(2) . . ? C6 C8 C15 122.78(19) . . ? C3 C9 C13 121.2(2) . . ? C3 C9 H9 119.4 . . ? C13 C9 H9 119.4 . . ? C14 C10 C3 118.85(19) . . ? C14 C10 C16 117.91(19) . . ? C3 C10 C16 123.23(17) . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C14 C12 C13 119.74(19) . . ? C14 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C9 119.8(2) . . ? C12 C13 H13 120.1 . . ? C9 C13 H13 120.1 . . ? C12 C14 C10 121.3(2) . . ? C12 C14 H14 119.3 . . ? C10 C14 H14 119.3 . . ? C21 C15 C8 117.6(2) . . ? C21 C15 H15A 107.9 . . ? C8 C15 H15A 107.9 . . ? C21 C15 H15B 107.9 . . ? C8 C15 H15B 107.9 . . ? H15A C15 H15B 107.2 . . ? C22 C16 C10 115.1(2) . . ? C22 C16 H16A 108.5 . . ? C10 C16 H16A 108.5 . . ? C22 C16 H16B 108.5 . . ? C10 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C7 C17 C20 119.1(2) . . ? C7 C17 H17 120.4 . . ? C20 C17 H17 120.4 . . ? C20 C18 C8 121.6(2) . . ? C20 C18 H18 119.2 . . ? C8 C18 H18 119.2 . . ? C18 C20 C17 120.2(2) . . ? C18 C20 H20 119.9 . . ? C17 C20 H20 119.9 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N1 C1 C4 108.64(15) . 2_685 ? N1 C1 C3 112.47(15) . . ? C4 C1 C3 107.98(15) 2_685 . ? N1 C1 H1A 109.7(11) . . ? C4 C1 H1A 110.1(11) 2_685 . ? C3 C1 H1A 108.0(10) . . ? N1 C4 C1 113.10(16) . 2_685 ? N1 C4 H4B 109.5(11) . . ? C1 C4 H4B 109.3(11) 2_685 . ? N1 C4 H4A 106.0(11) . . ? C1 C4 H4A 111.5(11) 2_685 . ? H4B C4 H4A 107.3(16) . . ? C21 C23 H23A 120.9(19) . . ? C21 C23 H23B 120(2) . . ? H23A C23 H23B 119(3) . . ? N2 C5 C2 108.59(15) . 2_576 ? N2 C5 C6 112.22(16) . . ? C2 C5 C6 108.89(16) 2_576 . ? N2 C5 H5A 108.6(11) . . ? C2 C5 H5A 107.4(11) 2_576 . ? C6 C5 H5A 110.9(11) . . ? N2 C2 C5 113.41(16) . 2_576 ? N2 C2 H2A 109.3(11) . . ? C5 C2 H2A 108.2(11) 2_576 . ? N2 C2 H2B 107.1(12) . . ? C5 C2 H2B 108.9(11) 2_576 . ? H2A C2 H2B 109.9(16) . . ? C24 C22 C16 128.1(3) . . ? C24 C22 H22A 119.0(17) . . ? C16 C22 H22A 112.9(16) . . ? C23 C21 C15 127.4(3) . . ? C23 C21 H21A 117.4(13) . . ? C15 C21 H21A 115.1(13) . . ? C22 C24 H24A 125(2) . . ? C22 C24 H24B 120(2) . . ? H24A C24 H24B 115(3) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.161 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.037 #===END data_2f _database_code_depnum_ccdc_archive 'CCDC 859215' #TrackingRef '- fileunico_pt263_pt43_pt231.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 Cl2 N2' _chemical_formula_weight 335.26 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' Cl Cl 0.1484 0.1585 '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 9.783(3) _cell_length_b 13.775(3) _cell_length_c 12.7176(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.574(18) _cell_angle_gamma 90.00 _cell_volume 1713.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3892 _cell_measurement_theta_min 5.03 _cell_measurement_theta_max 27.57 _exptl_crystal_description needle _exptl_crystal_colour white _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.377 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8794 _exptl_absorpt_correction_T_max 0.9562 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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-Nonius KappaCCD' _diffrn_measurement_method '\f scans 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 18747 _diffrn_reflns_av_R_equivalents 0.1125 _diffrn_reflns_av_sigmaI/netI 0.1349 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.03 _diffrn_reflns_theta_max 27.57 _reflns_number_total 3892 _reflns_number_gt 1435 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2002) ' _computing_cell_refinement 'DIRAX (Duisenberg,1992)' _computing_data_reduction 'EVAL (Nonius, 2002)' _computing_structure_solution 'SIR2011, updated version of SIR2008 (Burla et al., 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0457P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3892 _refine_ls_number_parameters 243 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2083 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1287 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.17474(9) 0.26090(7) 0.82834(8) 0.1027(4) Uani 1 1 d . . . Cl2 Cl 0.71567(12) -0.00017(7) 1.53686(6) 0.1163(4) Uani 1 1 d . . . N1 N 0.8250(2) 0.17862(16) 1.05250(17) 0.0584(6) Uani 1 1 d . . . N2 N 0.7772(2) 0.02400(17) 0.90671(16) 0.0603(7) Uani 1 1 d . . . C2 C 0.8163(3) 0.06174(19) 1.1992(2) 0.0531(7) Uani 1 1 d . . . C6 C 0.6092(3) 0.1594(2) 0.8652(2) 0.0561(8) Uani 1 1 d . . . C12 C 0.7545(4) 0.0242(2) 1.4062(2) 0.0699(9) Uani 1 1 d . . . C13 C 0.6995(4) -0.0464(2) 0.8453(2) 0.0816(10) Uani 1 1 d . . . H13A H 0.7164 -0.0365 0.7719 0.122 Uiso 1 1 calc R . . H13B H 0.6038 -0.0383 0.8587 0.122 Uiso 1 1 calc R . . H13C H 0.7271 -0.1108 0.8650 0.122 Uiso 1 1 calc R . . C15 C 0.9174(3) 0.2431(2) 1.1098(2) 0.0852(10) Uani 1 1 d . . . H15A H 0.9063 0.2336 1.1840 0.128 Uiso 1 1 calc R . . H15B H 0.8967 0.3093 1.0921 0.128 Uiso 1 1 calc R . . H15C H 1.0101 0.2288 1.0910 0.128 Uiso 1 1 calc R . . C18 C 0.3422(3) 0.2223(2) 0.8422(3) 0.0666(9) Uani 1 1 d . . . C1 C 0.7534(3) 0.0126(2) 1.0185(2) 0.0573(8) Uani 1 1 d . . . H1B H 0.772(3) -0.054(2) 1.0343(18) 0.069 Uiso 1 1 d . . . H1A H 0.657(3) 0.0207(18) 1.0396(18) 0.069 Uiso 1 1 d . . . C3 C 0.6633(4) 0.0729(2) 1.3454(3) 0.0669(9) Uani 1 1 d . . . H3 H 0.584(3) 0.098(2) 1.373(2) 0.080 Uiso 1 1 d . . . C4 C 0.6958(3) 0.0924(2) 1.2421(2) 0.0607(9) Uani 1 1 d . . . H4 H 0.635(3) 0.1233(19) 1.2021(19) 0.073 Uiso 1 1 d . . . C5 C 0.8465(3) 0.0772(2) 1.0839(2) 0.0553(8) Uani 1 1 d . . . H5 H 0.939(3) 0.0581(19) 1.0697(19) 0.066 Uiso 1 1 d . . . C7 C 0.9064(4) 0.0120(3) 1.2636(3) 0.0724(10) Uani 1 1 d . . . H7 H 0.989(3) -0.006(2) 1.240(2) 0.087 Uiso 1 1 d . . . C8 C 0.7556(3) 0.1249(2) 0.8732(2) 0.0614(9) Uani 1 1 d . . . H8 H 0.785(3) 0.1272(19) 0.802(2) 0.074 Uiso 1 1 d . . . C9 C 0.8482(3) 0.1880(3) 0.9395(3) 0.0685(9) Uani 1 1 d . . . H9A H 0.837(3) 0.254(2) 0.920(2) 0.082 Uiso 1 1 d . . . H9B H 0.942(3) 0.172(2) 0.926(2) 0.082 Uiso 1 1 d . . . C10 C 0.4072(4) 0.2313(2) 0.9370(2) 0.0655(9) Uani 1 1 d . . . H10 H 0.364(3) 0.2628(19) 0.995(2) 0.079 Uiso 1 1 d . . . C11 C 0.5393(3) 0.1998(2) 0.9482(2) 0.0611(9) Uani 1 1 d . . . H11 H 0.583(3) 0.2055(19) 1.011(2) 0.073 Uiso 1 1 d . . . C14 C 0.4078(4) 0.1835(3) 0.7590(3) 0.0797(11) Uani 1 1 d . . . H14 H 0.369(3) 0.176(2) 0.701(2) 0.096 Uiso 1 1 d . . . C16 C 0.5393(4) 0.1522(3) 0.7701(2) 0.0759(10) Uani 1 1 d . . . H16 H 0.588(3) 0.130(2) 0.714(2) 0.091 Uiso 1 1 d . . . C17 C 0.8761(4) -0.0063(3) 1.3665(3) 0.0824(11) Uani 1 1 d . . . H17 H 0.932(3) -0.040(2) 1.411(2) 0.099 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 Cl1 0.0598(6) 0.1210(8) 0.1270(8) 0.0444(6) -0.0155(5) -0.0119(6) Cl2 0.1653(10) 0.1247(9) 0.0590(5) 0.0073(5) 0.0076(6) -0.0109(7) N1 0.0547(16) 0.0502(16) 0.0702(16) -0.0007(12) -0.0019(13) -0.0078(13) N2 0.0692(18) 0.0580(16) 0.0539(14) -0.0030(13) 0.0080(12) -0.0007(13) C2 0.050(2) 0.0520(18) 0.0569(18) -0.0073(14) -0.0030(16) 0.0069(16) C6 0.062(2) 0.0527(19) 0.0541(18) 0.0087(15) 0.0030(17) -0.0065(16) C12 0.088(3) 0.071(2) 0.0507(18) -0.0056(17) -0.0016(19) -0.003(2) C13 0.114(3) 0.071(2) 0.0603(18) -0.0121(17) 0.0057(19) -0.002(2) C15 0.072(2) 0.079(2) 0.105(2) -0.0136(19) -0.014(2) -0.0213(19) C18 0.059(2) 0.072(2) 0.069(2) 0.0268(18) -0.0077(19) -0.0141(17) C1 0.063(2) 0.0541(19) 0.0552(18) 0.0018(16) 0.0062(16) -0.0007(19) C3 0.069(3) 0.065(2) 0.067(2) -0.0124(17) 0.010(2) 0.0033(19) C4 0.059(2) 0.063(2) 0.060(2) -0.0049(16) -0.0053(17) 0.0127(17) C5 0.0441(19) 0.058(2) 0.0640(19) -0.0046(15) 0.0020(16) 0.0041(16) C7 0.063(2) 0.090(3) 0.065(2) -0.0057(18) -0.007(2) 0.020(2) C8 0.066(2) 0.068(2) 0.0502(17) 0.0039(17) 0.0149(18) -0.0080(18) C9 0.059(2) 0.070(2) 0.076(2) 0.0116(19) 0.0091(19) -0.007(2) C10 0.064(2) 0.070(2) 0.062(2) 0.0139(16) 0.0030(18) -0.0005(19) C11 0.062(2) 0.068(2) 0.0535(18) 0.0046(17) -0.0060(18) -0.0018(18) C14 0.083(3) 0.090(3) 0.065(2) 0.015(2) -0.021(2) -0.013(2) C16 0.085(3) 0.091(3) 0.052(2) -0.0020(17) 0.002(2) -0.004(2) C17 0.093(3) 0.083(3) 0.071(2) 0.000(2) -0.023(2) 0.016(2) _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 Cl1 C18 1.730(3) . ? Cl2 C12 1.741(3) . ? N1 C15 1.457(3) . ? N1 C9 1.463(3) . ? N1 C5 1.468(3) . ? N2 C1 1.452(3) . ? N2 C13 1.454(3) . ? N2 C8 1.468(3) . ? C2 C4 1.372(4) . ? C2 C7 1.380(4) . ? C2 C5 1.513(4) . ? C6 C11 1.380(4) . ? C6 C16 1.388(4) . ? C6 C8 1.512(4) . ? C12 C3 1.353(4) . ? C12 C17 1.364(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C18 C14 1.352(4) . ? C18 C10 1.363(4) . ? C1 C5 1.516(4) . ? C1 H1B 0.96(3) . ? C1 H1A 0.99(3) . ? C3 C4 1.380(4) . ? C3 H3 0.92(3) . ? C4 H4 0.89(2) . ? C5 H5 0.96(3) . ? C7 C17 1.368(4) . ? C7 H7 0.90(3) . ? C8 C9 1.507(4) . ? C8 H8 0.96(2) . ? C9 H9A 0.95(3) . ? C9 H9B 0.96(3) . ? C10 C11 1.370(4) . ? C10 H10 0.96(3) . ? C11 H11 0.90(2) . ? C14 C16 1.363(4) . ? C14 H14 0.84(3) . ? C16 H16 0.92(3) . ? C17 H17 0.91(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 C15 N1 C9 109.6(2) . . ? C15 N1 C5 110.9(2) . . ? C9 N1 C5 109.2(2) . . ? C1 N2 C13 111.4(2) . . ? C1 N2 C8 111.3(2) . . ? C13 N2 C8 113.7(2) . . ? C4 C2 C7 117.6(3) . . ? C4 C2 C5 121.3(3) . . ? C7 C2 C5 121.0(3) . . ? C11 C6 C16 116.9(3) . . ? C11 C6 C8 123.5(3) . . ? C16 C6 C8 119.6(3) . . ? C3 C12 C17 120.9(3) . . ? C3 C12 Cl2 119.5(3) . . ? C17 C12 Cl2 119.5(3) . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C18 C10 120.5(3) . . ? C14 C18 Cl1 119.9(3) . . ? C10 C18 Cl1 119.6(3) . . ? N2 C1 C5 111.9(3) . . ? N2 C1 H1B 105.9(15) . . ? C5 C1 H1B 109.6(15) . . ? N2 C1 H1A 114.5(14) . . ? C5 C1 H1A 110.8(15) . . ? H1B C1 H1A 104(2) . . ? C12 C3 C4 118.9(3) . . ? C12 C3 H3 121.6(17) . . ? C4 C3 H3 119.3(17) . . ? C2 C4 C3 121.7(3) . . ? C2 C4 H4 119.7(18) . . ? C3 C4 H4 118.5(18) . . ? N1 C5 C2 111.6(2) . . ? N1 C5 C1 109.0(2) . . ? C2 C5 C1 109.1(2) . . ? N1 C5 H5 110.0(16) . . ? C2 C5 H5 109.8(15) . . ? C1 C5 H5 107.3(15) . . ? C17 C7 C2 121.1(3) . . ? C17 C7 H7 118.4(19) . . ? C2 C7 H7 120.4(19) . . ? N2 C8 C9 107.4(2) . . ? N2 C8 C6 116.8(2) . . ? C9 C8 C6 114.8(3) . . ? N2 C8 H8 105.3(16) . . ? C9 C8 H8 109.1(16) . . ? C6 C8 H8 102.7(15) . . ? N1 C9 C8 113.6(3) . . ? N1 C9 H9A 108.9(17) . . ? C8 C9 H9A 110.0(16) . . ? N1 C9 H9B 108.5(16) . . ? C8 C9 H9B 109.3(17) . . ? H9A C9 H9B 106(3) . . ? C18 C10 C11 119.6(3) . . ? C18 C10 H10 121.2(16) . . ? C11 C10 H10 119.1(16) . . ? C10 C11 C6 121.5(3) . . ? C10 C11 H11 120.2(18) . . ? C6 C11 H11 118.3(18) . . ? C18 C14 C16 120.0(3) . . ? C18 C14 H14 122(2) . . ? C16 C14 H14 118(2) . . ? C14 C16 C6 121.5(3) . . ? C14 C16 H16 121.3(19) . . ? C6 C16 H16 117.0(19) . . ? C12 C17 C7 119.7(3) . . ? C12 C17 H17 117(2) . . ? C7 C17 H17 123(2) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.139 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.034 #===END data_meso_2a _database_code_depnum_ccdc_archive 'CCDC 859216' #TrackingRef '- fileunico_pt263_pt43_pt231.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H11 N' _chemical_formula_weight 133.19 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 5.804(2) _cell_length_b 21.720(10) _cell_length_c 6.563(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.508(4) _cell_angle_gamma 90.00 _cell_volume 758.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 5.36 _cell_measurement_theta_max 27.52 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.166 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9665 _exptl_absorpt_correction_T_max 0.9731 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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-Nonius KappaCCD' _diffrn_measurement_method '\f scans 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 8529 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 5.36 _diffrn_reflns_theta_max 27.52 _reflns_number_total 1648 _reflns_number_gt 1045 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2002) ' _computing_cell_refinement 'DIRAX (Duisenberg,1992)' _computing_data_reduction 'EVAL (Nonius, 2002)' _computing_structure_solution 'SIR2011, updated version of SIR2008 (Burla et al., 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.1844P)^2^+0.8804P] 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 1648 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1601 _refine_ls_R_factor_gt 0.1174 _refine_ls_wR_factor_ref 0.3582 _refine_ls_wR_factor_gt 0.3181 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.2056(6) 0.04100(16) 0.5394(6) 0.0685(12) Uani 1 1 d . . . C2 C -0.0780(7) 0.11670(17) 0.2850(7) 0.0530(10) Uani 1 1 d . . . C3 C 0.3927(7) 0.08667(19) 0.6672(7) 0.0617(12) Uani 1 1 d . . . H3A H 0.5579 0.0693 0.7134 0.093 Uiso 1 1 calc R . . H3B H 0.3632 0.0985 0.7957 0.093 Uiso 1 1 calc R . . H3C H 0.3799 0.1222 0.5763 0.093 Uiso 1 1 calc R . . C4 C -0.1874(8) 0.21326(18) -0.0173(7) 0.0630(12) Uani 1 1 d . . . H4 H -0.2259 0.2456 -0.1183 0.076 Uiso 1 1 calc R . . C5 C 0.0341(8) 0.12065(19) 0.1350(8) 0.0646(13) Uani 1 1 d . . . H5 H 0.1478 0.0905 0.1350 0.078 Uiso 1 1 calc R . . C7 C -0.2424(8) 0.1621(2) 0.2805(7) 0.0613(11) Uani 1 1 d . . . H7 H -0.3184 0.1607 0.3812 0.074 Uiso 1 1 calc R . . C8 C -0.2982(8) 0.20950(19) 0.1322(8) 0.0641(12) Uani 1 1 d . . . H8 H -0.4122 0.2396 0.1324 0.077 Uiso 1 1 calc R . . C9 C -0.0204(9) 0.1690(2) -0.0159(7) 0.0621(12) Uani 1 1 d . . . H9 H 0.0569 0.1711 -0.1154 0.075 Uiso 1 1 calc R . . C1 C 0.2242(7) -0.01235(18) 0.6784(7) 0.0513(10) Uani 1 1 d . . . C6 C -0.0400(8) 0.0638(2) 0.4461(8) 0.0670(13) Uani 1 1 d . . . H6 H -0.0846 0.0783 0.5672 0.080 Uiso 1 1 calc R . . H1A H 0.188(10) -0.004(2) 0.806(9) 0.080 Uiso 1 1 d . . . H1B H 0.401(10) -0.032(2) 0.716(9) 0.080 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 0.0495(19) 0.057(2) 0.068(2) 0.0187(17) -0.0096(16) -0.0179(15) C2 0.0438(18) 0.048(2) 0.054(2) 0.0056(16) 0.0052(16) -0.0112(16) C3 0.048(2) 0.060(2) 0.061(2) 0.0060(18) 0.0049(18) -0.0175(17) C4 0.067(3) 0.047(2) 0.057(2) 0.0088(18) 0.006(2) -0.0059(18) C5 0.051(2) 0.049(2) 0.079(3) -0.009(2) 0.011(2) 0.0088(17) C7 0.054(2) 0.069(3) 0.058(2) 0.000(2) 0.0198(19) -0.0085(19) C8 0.062(2) 0.051(2) 0.070(3) -0.0020(19) 0.016(2) 0.0081(19) C9 0.066(3) 0.066(3) 0.056(2) 0.003(2) 0.026(2) -0.006(2) C1 0.0381(18) 0.050(2) 0.051(2) 0.0126(16) 0.0029(16) -0.0065(15) C6 0.053(2) 0.055(2) 0.073(3) 0.015(2) 0.003(2) -0.0116(18) _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 C6 1.399(6) . ? N1 C3 1.463(5) . ? N1 C1 1.452(5) . ? C2 C7 1.364(6) . ? C2 C5 1.383(6) . ? C2 C6 1.516(5) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C9 1.362(6) . ? C4 C8 1.374(6) . ? C4 H4 0.9300 . ? C5 C9 1.391(6) . ? C5 H5 0.9300 . ? C7 C8 1.364(6) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C1 C6 1.538(5) 3_556 ? C1 H1A 0.96(5) . ? C1 H1B 1.04(5) . ? C6 C1 1.538(5) 3_556 ? C6 H6 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 C6 N1 C3 113.8(4) . . ? C6 N1 C1 111.4(3) . . ? C3 N1 C1 109.2(3) . . ? C7 C2 C5 117.6(4) . . ? C7 C2 C6 118.0(4) . . ? C5 C2 C6 124.4(4) . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C9 C4 C8 119.2(4) . . ? C9 C4 H4 120.4 . . ? C8 C4 H4 120.4 . . ? C2 C5 C9 121.0(4) . . ? C2 C5 H5 119.5 . . ? C9 C5 H5 119.5 . . ? C8 C7 C2 121.8(4) . . ? C8 C7 H7 119.1 . . ? C2 C7 H7 119.1 . . ? C7 C8 C4 120.6(4) . . ? C7 C8 H8 119.7 . . ? C4 C8 H8 119.7 . . ? C4 C9 C5 119.8(4) . . ? C4 C9 H9 120.1 . . ? C5 C9 H9 120.1 . . ? N1 C1 C6 112.6(3) . 3_556 ? N1 C1 H1A 114(3) . . ? C6 C1 H1A 105(3) 3_556 . ? N1 C1 H1B 107(3) . . ? C6 C1 H1B 104(3) 3_556 . ? H1A C1 H1B 114(5) . . ? N1 C6 C2 114.4(4) . . ? N1 C6 C1 110.2(4) . 3_556 ? C2 C6 C1 107.7(3) . 3_556 ? N1 C6 H6 108.1 . . ? C2 C6 H6 108.1 . . ? C1 C6 H6 108.1 3_556 . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.943 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.078