# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 837072' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H19 N O' _chemical_formula_weight 217.30 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.493(5) _cell_length_b 11.707(5) _cell_length_c 12.816(6) _cell_angle_alpha 79.59(3) _cell_angle_beta 73.54(4) _cell_angle_gamma 73.58(3) _cell_volume 1302.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.108 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8043 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0838 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 20.23 _reflns_number_total 2452 _reflns_number_gt 1125 _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^)+(0.1000P)^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 2452 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1314 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.2003 _refine_ls_wR_factor_gt 0.1619 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _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 N2 N 0.2253(4) 0.5580(4) 0.8093(3) 0.0797(13) Uani 1 1 d . . . H2 H 0.3178 0.5464 0.8121 0.096 Uiso 1 1 calc R . . C1 C 0.7854(5) 0.3625(5) 0.6819(4) 0.0769(15) Uani 1 1 d . . . H1 H 0.6854 0.3890 0.6659 0.092 Uiso 1 1 calc R . . N1 N 0.7847(5) 0.4319(4) 0.7647(3) 0.0869(14) Uani 1 1 d . . . H1A H 0.8705 0.4298 0.7760 0.104 Uiso 1 1 calc R . . C21 C 0.1820(7) 0.4657(5) 0.7954(4) 0.0763(16) Uani 1 1 d . . . C15 C 0.1285(6) 0.6775(5) 0.8202(4) 0.0801(16) Uani 1 1 d . . . H15 H 0.0437 0.6844 0.7883 0.096 Uiso 1 1 calc R . . C7 C 0.6615(7) 0.4985(5) 0.8243(4) 0.0774(16) Uani 1 1 d . . . C20 C 0.0637(6) 0.7005(5) 0.9376(4) 0.1008(18) Uani 1 1 d . . . H20A H 0.1455 0.6907 0.9722 0.121 Uiso 1 1 calc R . . H20B H 0.0058 0.6425 0.9755 0.121 Uiso 1 1 calc R . . C9 C 0.6222(7) 0.6965(6) 0.8869(6) 0.0871(17) Uani 1 1 d . . . C19 C -0.0391(7) 0.8274(6) 0.9475(5) 0.123(2) Uani 1 1 d . . . H19A H -0.1281 0.8339 0.9217 0.147 Uiso 1 1 calc R . . H19B H -0.0726 0.8421 1.0238 0.147 Uiso 1 1 calc R . . C6 C 0.9002(7) 0.3867(5) 0.5787(4) 0.1086(19) Uani 1 1 d . . . H6A H 0.9994 0.3667 0.5937 0.130 Uiso 1 1 calc R . . H6B H 0.8754 0.4713 0.5528 0.130 Uiso 1 1 calc R . . C2 C 0.8132(7) 0.2322(5) 0.7185(5) 0.118(2) Uani 1 1 d . . . H2A H 0.7343 0.2181 0.7829 0.142 Uiso 1 1 calc R . . H2B H 0.9094 0.2050 0.7386 0.142 Uiso 1 1 calc R . . C3 C 0.8160(9) 0.1600(5) 0.6296(7) 0.145(3) Uani 1 1 d . . . H3A H 0.8376 0.0753 0.6557 0.174 Uiso 1 1 calc R . . H3B H 0.7174 0.1824 0.6132 0.174 Uiso 1 1 calc R . . C18 C 0.0425(8) 0.9199(5) 0.8820(5) 0.128(2) Uani 1 1 d . . . H18A H 0.1225 0.9211 0.9147 0.154 Uiso 1 1 calc R . . H18B H -0.0279 0.9983 0.8846 0.154 Uiso 1 1 calc R . . C5 C 0.9045(8) 0.3139(7) 0.4905(5) 0.144(3) Uani 1 1 d . . . H5A H 0.8083 0.3399 0.4704 0.173 Uiso 1 1 calc R . . H5B H 0.9830 0.3288 0.4259 0.173 Uiso 1 1 calc R . . C13 C 0.4543(11) 0.8824(9) 0.9454(9) 0.168(4) Uani 1 1 d . . . H13 H 0.3765 0.9238 0.9978 0.201 Uiso 1 1 calc R . . C10 C 0.6845(9) 0.7605(9) 0.7926(7) 0.134(3) Uani 1 1 d . . . H10 H 0.7652 0.7210 0.7407 0.160 Uiso 1 1 calc R . . C12 C 0.5191(18) 0.9434(12) 0.8501(11) 0.211(8) Uani 1 1 d . . . H12 H 0.4874 1.0263 0.8381 0.254 Uiso 1 1 calc R . . C4 C 0.9349(9) 0.1827(7) 0.5274(7) 0.152(3) Uani 1 1 d . . . H4A H 1.0345 0.1545 0.5421 0.183 Uiso 1 1 calc R . . H4B H 0.9327 0.1394 0.4703 0.183 Uiso 1 1 calc R . . C8 C 0.6850(6) 0.5652(5) 0.9047(4) 0.0875(16) Uani 1 1 d . . . H8A H 0.6373 0.5357 0.9782 0.105 Uiso 1 1 calc R . . H8B H 0.7927 0.5494 0.8991 0.105 Uiso 1 1 calc R . . O2 O 0.0534(4) 0.4730(3) 0.7886(3) 0.1079(14) Uani 1 1 d . . . O1 O 0.5344(4) 0.5042(3) 0.8147(3) 0.1079(14) Uani 1 1 d . . . C11 C 0.6290(16) 0.8815(13) 0.7743(11) 0.204(6) Uani 1 1 d . . . H11 H 0.6682 0.9221 0.7078 0.245 Uiso 1 1 calc R . . C16 C 0.2134(6) 0.7705(5) 0.7560(4) 0.1052(19) Uani 1 1 d . . . H16A H 0.2998 0.7645 0.7846 0.126 Uiso 1 1 calc R . . H16B H 0.2507 0.7554 0.6798 0.126 Uiso 1 1 calc R . . C17 C 0.1101(8) 0.8953(5) 0.7643(5) 0.131(2) Uani 1 1 d . . . H17A H 0.1672 0.9538 0.7262 0.157 Uiso 1 1 calc R . . H17B H 0.0293 0.9036 0.7290 0.157 Uiso 1 1 calc R . . C14 C 0.5054(8) 0.7593(7) 0.9631(5) 0.115(2) Uani 1 1 d . . . H14 H 0.4604 0.7181 1.0273 0.138 Uiso 1 1 calc R . . C23 C 0.3362(6) 0.3031(6) 0.6776(5) 0.0776(16) Uani 1 1 d . . . C22 C 0.2998(5) 0.3472(4) 0.7865(4) 0.0851(16) Uani 1 1 d . . . H22A H 0.3918 0.3564 0.7993 0.102 Uiso 1 1 calc R . . H22B H 0.2629 0.2879 0.8429 0.102 Uiso 1 1 calc R . . C28 C 0.3234(6) 0.1925(6) 0.6713(5) 0.110(2) Uani 1 1 d . . . H28 H 0.2892 0.1460 0.7354 0.132 Uiso 1 1 calc R . . C26 C 0.4151(8) 0.2141(8) 0.4781(7) 0.127(3) Uani 1 1 d . . . H26 H 0.4455 0.1833 0.4110 0.153 Uiso 1 1 calc R . . C25 C 0.4246(7) 0.3247(7) 0.4843(6) 0.124(2) Uani 1 1 d . . . H25 H 0.4553 0.3724 0.4201 0.148 Uiso 1 1 calc R . . C27 C 0.3593(8) 0.1469(6) 0.5729(8) 0.133(2) Uani 1 1 d . . . H27 H 0.3462 0.0718 0.5702 0.160 Uiso 1 1 calc R . . C24 C 0.3904(7) 0.3689(5) 0.5823(6) 0.1012(19) Uani 1 1 d . . . H24 H 0.4041 0.4439 0.5845 0.121 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 N2 0.056(3) 0.091(3) 0.101(3) -0.027(3) -0.028(2) -0.013(3) C1 0.063(4) 0.081(4) 0.096(4) -0.017(3) -0.022(3) -0.026(3) N1 0.056(3) 0.115(4) 0.099(3) -0.031(3) -0.027(3) -0.018(3) C21 0.066(5) 0.097(5) 0.071(3) -0.022(3) -0.010(3) -0.028(4) C15 0.064(4) 0.093(4) 0.084(4) -0.022(3) -0.015(3) -0.014(4) C7 0.069(5) 0.087(4) 0.077(4) -0.006(3) -0.028(4) -0.013(4) C20 0.106(5) 0.100(5) 0.083(4) -0.021(3) -0.002(3) -0.019(4) C9 0.079(5) 0.106(5) 0.092(5) -0.017(5) -0.035(4) -0.030(4) C19 0.127(6) 0.119(5) 0.106(5) -0.043(4) -0.005(4) -0.010(5) C6 0.128(6) 0.124(5) 0.081(4) -0.004(4) -0.014(4) -0.058(4) C2 0.141(6) 0.092(5) 0.120(5) 0.002(4) -0.032(4) -0.035(4) C3 0.179(8) 0.091(5) 0.180(7) -0.031(5) -0.062(7) -0.028(5) C18 0.155(7) 0.100(5) 0.122(6) -0.030(4) -0.028(5) -0.014(5) C5 0.180(7) 0.167(7) 0.094(5) -0.040(5) -0.015(5) -0.057(6) C13 0.191(9) 0.104(7) 0.235(12) -0.080(7) -0.114(9) 0.022(7) C10 0.153(7) 0.146(7) 0.126(7) -0.002(6) -0.038(5) -0.079(7) C12 0.36(2) 0.111(10) 0.257(18) 0.020(9) -0.223(17) -0.074(11) C4 0.152(8) 0.152(7) 0.156(8) -0.075(6) -0.055(6) 0.011(6) C8 0.073(4) 0.114(5) 0.078(4) -0.024(4) -0.017(3) -0.019(4) O2 0.055(3) 0.129(3) 0.155(4) -0.050(2) -0.028(3) -0.024(2) O1 0.056(3) 0.146(3) 0.135(3) -0.047(2) -0.032(3) -0.016(2) C11 0.316(18) 0.185(14) 0.192(12) 0.022(9) -0.150(12) -0.128(13) C16 0.106(5) 0.111(5) 0.088(4) -0.023(4) -0.005(4) -0.020(4) C17 0.166(7) 0.112(5) 0.099(5) -0.020(4) -0.014(4) -0.023(5) C14 0.107(6) 0.129(7) 0.117(5) -0.052(5) -0.037(5) -0.010(4) C23 0.063(4) 0.073(4) 0.098(5) -0.031(4) -0.018(3) -0.007(3) C22 0.075(4) 0.081(4) 0.100(4) -0.014(3) -0.025(3) -0.015(3) C28 0.114(5) 0.108(6) 0.106(5) -0.032(4) -0.019(4) -0.018(4) C26 0.117(6) 0.133(7) 0.131(7) -0.063(6) -0.022(5) -0.008(5) C25 0.125(6) 0.127(6) 0.086(5) -0.011(5) -0.004(4) 0.000(5) C27 0.128(7) 0.121(6) 0.156(7) -0.047(6) -0.022(6) -0.031(5) C24 0.104(5) 0.098(5) 0.092(5) -0.007(5) -0.005(4) -0.031(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C21 1.315(6) . ? N2 C15 1.447(5) . ? C1 N1 1.446(5) . ? C1 C2 1.483(6) . ? C1 C6 1.496(6) . ? N1 C7 1.324(6) . ? C21 O2 1.226(5) . ? C21 C22 1.516(6) . ? C15 C20 1.497(6) . ? C15 C16 1.520(6) . ? C7 O1 1.229(5) . ? C7 C8 1.497(6) . ? C20 C19 1.534(6) . ? C9 C10 1.375(8) . ? C9 C14 1.382(7) . ? C9 C8 1.483(7) . ? C19 C18 1.502(7) . ? C6 C5 1.519(7) . ? C2 C3 1.527(7) . ? C3 C4 1.506(9) . ? C18 C17 1.509(7) . ? C5 C4 1.494(8) . ? C13 C12 1.374(13) . ? C13 C14 1.384(8) . ? C10 C11 1.367(12) . ? C12 C11 1.345(16) . ? C16 C17 1.515(6) . ? C23 C28 1.353(7) . ? C23 C24 1.370(7) . ? C23 C22 1.489(6) . ? C28 C27 1.374(8) . ? C26 C25 1.340(8) . ? C26 C27 1.378(8) . ? C25 C24 1.364(7) . ? 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 C21 N2 C15 124.7(5) . . ? N1 C1 C2 112.6(5) . . ? N1 C1 C6 110.0(4) . . ? C2 C1 C6 110.5(4) . . ? C7 N1 C1 124.7(4) . . ? O2 C21 N2 122.8(5) . . ? O2 C21 C22 120.2(5) . . ? N2 C21 C22 116.9(5) . . ? N2 C15 C20 112.0(4) . . ? N2 C15 C16 110.5(5) . . ? C20 C15 C16 111.3(4) . . ? O1 C7 N1 121.6(5) . . ? O1 C7 C8 121.8(5) . . ? N1 C7 C8 116.6(5) . . ? C15 C20 C19 111.3(4) . . ? C10 C9 C14 117.7(7) . . ? C10 C9 C8 119.5(7) . . ? C14 C9 C8 122.8(7) . . ? C18 C19 C20 111.2(5) . . ? C1 C6 C5 111.2(5) . . ? C1 C2 C3 112.0(5) . . ? C4 C3 C2 110.4(6) . . ? C19 C18 C17 112.0(5) . . ? C4 C5 C6 112.1(5) . . ? C12 C13 C14 119.7(11) . . ? C11 C10 C9 120.7(10) . . ? C11 C12 C13 119.2(15) . . ? C5 C4 C3 109.2(6) . . ? C9 C8 C7 112.9(4) . . ? C12 C11 C10 121.6(16) . . ? C17 C16 C15 110.4(5) . . ? C18 C17 C16 111.3(5) . . ? C9 C14 C13 121.0(7) . . ? C28 C23 C24 118.0(5) . . ? C28 C23 C22 119.9(6) . . ? C24 C23 C22 122.0(6) . . ? C23 C22 C21 112.7(4) . . ? C23 C28 C27 122.0(6) . . ? C25 C26 C27 118.8(7) . . ? C26 C25 C24 121.7(7) . . ? C28 C27 C26 119.1(7) . . ? C25 C24 C23 120.3(6) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 20.23 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.169 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.046 data_tk4 _database_code_depnum_ccdc_archive 'CCDC 837222' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 N2 O2' _chemical_compound_source Synthesised _exptl_crystal_recrystallization_method Methanol _chemical_melting_point ? _exptl_crystal_description rod _exptl_crystal_colour colourless _diffrn_ambient_temperature 296(2) _chemical_formula_weight 268.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_int_tables_number 29 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 10.0436(5) _cell_length_b 14.5106(8) _cell_length_c 9.4623(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1379.02(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2022 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 18.69 _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17142 _diffrn_reflns_av_R_equivalents 0.1407 _diffrn_reflns_av_sigmaI/netI 0.1426 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 28.33 _reflns_number_total 3382 _reflns_number_gt 1342 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(18) _refine_ls_number_reflns 3382 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1304 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1419 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 0.595 _refine_ls_restrained_S_all 0.595 _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 0.2174(2) 0.51815(15) 0.4730(3) 0.0491(6) Uani 1 1 d . . . H1 H 0.1374 0.5064 0.5000 0.059 Uiso 1 1 calc R . . C11 C 0.1759(3) 0.90166(19) 0.4576(3) 0.0454(7) Uani 1 1 d . . . C2 C 0.2844(3) 0.39592(19) 0.6312(3) 0.0454(7) Uani 1 1 d . . . C12 C 0.0695(3) 0.8619(2) 0.5274(3) 0.0550(8) Uani 1 1 d . . . H12 H 0.0553 0.7987 0.5199 0.066 Uiso 1 1 calc R . . C9 C 0.2632(3) 0.6836(2) 0.4321(3) 0.0466(7) Uani 1 1 d . . . C8 C 0.2387(3) 0.58876(19) 0.3686(3) 0.0523(8) Uani 1 1 d . . . H8A H 0.1615 0.5918 0.3073 0.063 Uiso 1 1 calc R . . H8B H 0.3147 0.5719 0.3108 0.063 Uiso 1 1 calc R . . C5 C 0.2360(4) 0.2547(2) 0.8243(4) 0.0735(10) Uani 1 1 d . . . H5 H 0.2203 0.2075 0.8887 0.088 Uiso 1 1 calc R . . C6 C 0.1317(3) 0.2946(2) 0.7504(4) 0.0686(10) Uani 1 1 d . . . H6 H 0.0450 0.2743 0.7649 0.082 Uiso 1 1 calc R . . C14 C 0.0059(4) 1.0088(3) 0.6221(4) 0.0724(10) Uani 1 1 d . . . H14 H -0.0491 1.0442 0.6795 0.087 Uiso 1 1 calc R . . C15 C 0.1089(4) 1.0489(2) 0.5509(4) 0.0729(10) Uani 1 1 d . . . H15 H 0.1222 1.1122 0.5575 0.088 Uiso 1 1 calc R . . C10 C 0.2795(3) 0.84800(19) 0.3767(3) 0.0585(9) Uani 1 1 d . . . H10A H 0.2980 0.8806 0.2894 0.070 Uiso 1 1 calc R . . H10B H 0.3610 0.8477 0.4318 0.070 Uiso 1 1 calc R . . C16 C 0.1931(3) 0.9962(2) 0.4696(4) 0.0626(9) Uani 1 1 d . . . H16 H 0.2629 1.0245 0.4217 0.075 Uiso 1 1 calc R . . C3 C 0.3880(3) 0.3548(3) 0.7045(4) 0.0674(10) Uani 1 1 d . . . H3 H 0.4751 0.3738 0.6884 0.081 Uiso 1 1 calc R . . C4 C 0.3631(4) 0.2861(3) 0.8007(4) 0.0811(11) Uani 1 1 d . . . H4 H 0.4336 0.2604 0.8508 0.097 Uiso 1 1 calc R . . C1 C 0.3182(3) 0.47006(19) 0.5295(3) 0.0486(7) Uani 1 1 d . . . N2 N 0.2461(2) 0.75291(15) 0.3417(3) 0.0526(6) Uani 1 1 d . . . H2 H 0.2141 0.7411 0.2594 0.063 Uiso 1 1 calc R . . C13 C -0.0162(3) 0.9150(3) 0.6083(4) 0.0658(9) Uani 1 1 d . . . H13 H -0.0885 0.8876 0.6534 0.079 Uiso 1 1 calc R . . C7 C 0.1568(3) 0.3647(2) 0.6552(3) 0.0572(8) Uani 1 1 d . . . H7 H 0.0863 0.3914 0.6064 0.069 Uiso 1 1 calc R . . O2 O 0.2992(2) 0.69529(15) 0.5535(2) 0.0649(6) Uani 1 1 d . . . O1 O 0.43469(18) 0.48734(14) 0.4952(3) 0.0689(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0318(12) 0.0556(14) 0.0600(17) 0.0002(14) 0.0049(11) -0.0025(11) C11 0.0408(15) 0.0516(17) 0.0438(16) -0.0009(14) -0.0026(13) -0.0028(13) C2 0.0398(16) 0.0441(16) 0.0523(17) -0.0101(14) -0.0028(13) 0.0067(13) C12 0.0453(16) 0.0596(18) 0.0600(19) 0.0082(16) -0.0024(16) -0.0009(14) C9 0.0465(17) 0.0552(18) 0.0381(16) -0.0043(16) 0.0027(13) -0.0059(14) C8 0.0551(18) 0.0565(18) 0.0453(16) -0.0027(17) 0.0005(14) -0.0070(15) C5 0.089(3) 0.0569(19) 0.074(2) 0.0105(19) 0.003(2) 0.017(2) C6 0.061(2) 0.061(2) 0.084(2) 0.0123(19) 0.014(2) 0.0027(18) C14 0.065(2) 0.079(3) 0.074(2) -0.005(2) 0.0029(19) 0.0244(19) C15 0.069(2) 0.059(2) 0.091(3) -0.006(2) -0.001(2) 0.0061(17) C10 0.063(2) 0.056(2) 0.0562(19) -0.0039(16) 0.0118(16) -0.0122(15) C16 0.0556(19) 0.059(2) 0.074(2) -0.0067(19) 0.0010(18) -0.0044(15) C3 0.0453(19) 0.069(2) 0.088(2) -0.008(2) -0.0107(18) 0.0103(17) C4 0.081(3) 0.072(3) 0.090(3) 0.007(2) -0.026(2) 0.022(2) C1 0.0293(15) 0.0552(17) 0.0612(19) -0.0156(16) 0.0035(15) -0.0034(13) N2 0.0674(16) 0.0523(14) 0.0382(13) -0.0027(13) 0.0019(12) -0.0089(13) C13 0.0497(19) 0.078(2) 0.070(2) 0.0144(19) 0.0053(17) 0.0083(17) C7 0.0470(18) 0.0573(19) 0.067(2) 0.0058(16) 0.0022(16) 0.0042(15) O2 0.0829(15) 0.0688(14) 0.0429(13) -0.0103(11) -0.0084(11) 0.0033(10) O1 0.0304(11) 0.0879(15) 0.0884(16) -0.0069(13) 0.0057(11) -0.0063(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.341(3) . ? N1 C8 1.439(4) . ? C11 C12 1.382(4) . ? C11 C16 1.387(4) . ? C11 C10 1.509(4) . ? C2 C7 1.377(4) . ? C2 C3 1.386(4) . ? C2 C1 1.483(4) . ? C12 C13 1.387(4) . ? C9 O2 1.216(3) . ? C9 N2 1.331(3) . ? C9 C8 1.522(4) . ? C5 C4 1.374(5) . ? C5 C6 1.386(5) . ? C6 C7 1.383(4) . ? C14 C15 1.364(5) . ? C14 C13 1.386(5) . ? C15 C16 1.376(4) . ? C10 N2 1.458(3) . ? C3 C4 1.371(5) . ? C1 O1 1.240(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 C8 122.2(2) . . ? C12 C11 C16 118.1(3) . . ? C12 C11 C10 124.1(3) . . ? C16 C11 C10 117.7(3) . . ? C7 C2 C3 118.3(3) . . ? C7 C2 C1 123.9(3) . . ? C3 C2 C1 117.8(3) . . ? C11 C12 C13 120.8(3) . . ? O2 C9 N2 122.7(3) . . ? O2 C9 C8 123.2(3) . . ? N2 C9 C8 114.1(2) . . ? N1 C8 C9 113.4(2) . . ? C4 C5 C6 118.8(3) . . ? C7 C6 C5 119.9(3) . . ? C15 C14 C13 119.6(3) . . ? C14 C15 C16 120.3(3) . . ? N2 C10 C11 116.4(2) . . ? C15 C16 C11 121.2(3) . . ? C4 C3 C2 120.5(3) . . ? C3 C4 C5 121.2(3) . . ? O1 C1 N1 120.2(3) . . ? O1 C1 C2 122.2(3) . . ? N1 C1 C2 117.6(2) . . ? C9 N2 C10 122.6(3) . . ? C14 C13 C12 119.9(3) . . ? C2 C7 C6 121.3(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.120 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.043