data_F:\structures\sm08\sm08_all.CIF _audit_creation_method SHELXL-97 _chemical_name_systematic ; JA037713C ; _chemical_name_common 'sm08' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N2 O2' _chemical_formula_weight 266.29 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8600(7) _cell_length_b 8.4944(10) _cell_length_c 13.4511(17) _cell_angle_alpha 101.721(2) _cell_angle_beta 98.011(2) _cell_angle_gamma 99.562(2) _cell_volume 636.01(13) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas '0' _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.093 _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 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-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 3280 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2189 _reflns_number_gt 1954 _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^)+(0.1197P)^2^+0.1428P] 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 0.000 _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2189 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0602 _refine_ls_wR_factor_ref 0.1701 _refine_ls_wR_factor_gt 0.1569 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.012 _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 O1 O 0.03160(19) 1.07678(14) 0.13694(9) 0.0320(4) Uani 1 1 d . . . H1 H 0.0534 0.9919 0.0981 0.048 Uiso 1 1 calc R . . O2 O 1.0051(2) 0.66737(15) 0.22549(9) 0.0333(4) Uani 1 1 d . . . H2 H 0.9248 0.6621 0.1677 0.050 Uiso 1 1 calc R . . N1 N 0.2615(2) 0.85725(16) 0.06982(10) 0.0294(4) Uani 1 1 d . . . N2 N 0.6623(2) 0.71583(16) 0.09823(10) 0.0276(4) Uani 1 1 d . . . C1 C 0.4282(3) 1.07368(19) 0.21612(11) 0.0246(4) Uani 1 1 d . . . C2 C 0.2328(3) 1.1508(2) 0.20420(12) 0.0265(4) Uani 1 1 d . . . C3 C 0.2455(3) 1.3092(2) 0.26171(12) 0.0290(4) Uani 1 1 d . . . H3 H 0.1126 1.3593 0.2551 0.035 Uiso 1 1 calc R . . C4 C 0.4500(3) 1.3937(2) 0.32837(13) 0.0302(4) Uani 1 1 d . . . H4 H 0.4569 1.5015 0.3675 0.036 Uiso 1 1 calc R . . C5 C 0.6461(3) 1.32152(19) 0.33842(12) 0.0292(4) Uani 1 1 d . . . H5 H 0.7875 1.3807 0.3832 0.035 Uiso 1 1 calc R . . C6 C 0.6344(3) 1.16405(19) 0.28321(12) 0.0261(4) Uani 1 1 d . . . H6 H 0.7688 1.1156 0.2907 0.031 Uiso 1 1 calc R . . C7 C 0.4206(3) 0.90991(19) 0.15173(12) 0.0257(4) Uani 1 1 d . . . C8 C 0.2840(3) 0.7096(2) -0.00324(13) 0.0336(4) Uani 1 1 d . . . H8A H 0.1993 0.7060 -0.0730 0.040 Uiso 1 1 calc R . . H8B H 0.2147 0.6104 0.0184 0.040 Uiso 1 1 calc R . . C9 C 0.5417(3) 0.7143(2) -0.00530(12) 0.0321(4) Uani 1 1 d . . . H9A H 0.5611 0.6170 -0.0556 0.038 Uiso 1 1 calc R . . H9B H 0.6108 0.8139 -0.0268 0.038 Uiso 1 1 calc R . . C10 C 0.5980(3) 0.80491(18) 0.17449(12) 0.0245(4) Uani 1 1 d . . . C11 C 0.6900(3) 0.79662(18) 0.28032(12) 0.0238(4) Uani 1 1 d . . . C12 C 0.5752(3) 0.84558(18) 0.36247(12) 0.0249(4) Uani 1 1 d . . . H12 H 0.4349 0.8861 0.3495 0.030 Uiso 1 1 calc R . . C13 C 0.6600(3) 0.83664(19) 0.46167(12) 0.0280(4) Uani 1 1 d . . . H13 H 0.5782 0.8695 0.5161 0.034 Uiso 1 1 calc R . . C14 C 0.8675(3) 0.7788(2) 0.48120(13) 0.0299(4) Uani 1 1 d . . . H14 H 0.9301 0.7760 0.5497 0.036 Uiso 1 1 calc R . . C15 C 0.9818(3) 0.72577(19) 0.40200(13) 0.0285(4) Uani 1 1 d . . . H15 H 1.1225 0.6863 0.4162 0.034 Uiso 1 1 calc R . . C16 C 0.8925(3) 0.72953(19) 0.30103(13) 0.0264(4) 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 0.0288(7) 0.0324(7) 0.0330(7) 0.0044(5) 0.0001(5) 0.0093(5) O2 0.0328(7) 0.0395(7) 0.0327(7) 0.0109(5) 0.0099(5) 0.0147(5) N1 0.0335(8) 0.0273(8) 0.0258(8) 0.0054(6) 0.0010(6) 0.0064(6) N2 0.0322(8) 0.0242(7) 0.0267(8) 0.0056(5) 0.0065(6) 0.0059(6) C1 0.0277(8) 0.0253(8) 0.0230(8) 0.0086(6) 0.0069(6) 0.0058(6) C2 0.0277(8) 0.0295(9) 0.0253(8) 0.0113(6) 0.0069(6) 0.0066(6) C3 0.0312(9) 0.0289(9) 0.0319(9) 0.0111(7) 0.0105(7) 0.0111(7) C4 0.0372(9) 0.0236(8) 0.0321(9) 0.0066(7) 0.0107(7) 0.0085(7) C5 0.0305(9) 0.0259(9) 0.0296(9) 0.0063(7) 0.0032(7) 0.0030(7) C6 0.0277(8) 0.0256(8) 0.0278(8) 0.0095(6) 0.0071(6) 0.0074(6) C7 0.0284(8) 0.0259(8) 0.0253(8) 0.0094(6) 0.0060(6) 0.0069(6) C8 0.0418(10) 0.0283(9) 0.0276(9) 0.0027(7) -0.0016(7) 0.0095(7) C9 0.0457(10) 0.0288(9) 0.0233(8) 0.0068(6) 0.0067(7) 0.0106(7) C10 0.0257(8) 0.0201(8) 0.0273(8) 0.0049(6) 0.0058(6) 0.0033(6) C11 0.0257(8) 0.0185(8) 0.0268(8) 0.0053(6) 0.0045(6) 0.0035(6) C12 0.0265(8) 0.0191(8) 0.0286(9) 0.0049(6) 0.0039(6) 0.0044(6) C13 0.0333(9) 0.0236(8) 0.0264(8) 0.0041(6) 0.0064(7) 0.0052(7) C14 0.0320(9) 0.0267(8) 0.0278(9) 0.0069(6) -0.0011(7) 0.0019(7) C15 0.0250(8) 0.0259(9) 0.0354(9) 0.0104(7) 0.0029(7) 0.0053(6) C16 0.0263(8) 0.0229(8) 0.0308(9) 0.0072(6) 0.0068(6) 0.0045(6) _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 C2 1.352(2) . ? O2 C16 1.3535(19) . ? N1 C7 1.288(2) . ? N1 C8 1.465(2) . ? N2 C10 1.286(2) . ? N2 C9 1.468(2) . ? C1 C6 1.404(2) . ? C1 C2 1.417(2) . ? C1 C7 1.472(2) . ? C2 C3 1.393(2) . ? C3 C4 1.382(2) . ? C4 C5 1.393(2) . ? C5 C6 1.377(2) . ? C7 C10 1.517(2) . ? C8 C9 1.508(3) . ? C10 C11 1.470(2) . ? C11 C12 1.400(2) . ? C11 C16 1.417(2) . ? C12 C13 1.379(2) . ? C13 C14 1.397(2) . ? C14 C15 1.375(2) . ? C15 C16 1.395(2) . ? 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 C7 N1 C8 117.09(13) . . ? C10 N2 C9 116.38(13) . . ? C6 C1 C2 118.05(15) . . ? C6 C1 C7 121.40(14) . . ? C2 C1 C7 120.26(14) . . ? O1 C2 C3 117.83(14) . . ? O1 C2 C1 122.20(14) . . ? C3 C2 C1 119.96(15) . . ? C4 C3 C2 120.46(15) . . ? C3 C4 C5 120.22(15) . . ? C6 C5 C4 119.83(15) . . ? C5 C6 C1 121.41(14) . . ? N1 C7 C1 118.00(14) . . ? N1 C7 C10 118.79(14) . . ? C1 C7 C10 123.14(13) . . ? N1 C8 C9 108.42(14) . . ? N2 C9 C8 108.98(13) . . ? N2 C10 C11 119.29(13) . . ? N2 C10 C7 118.58(14) . . ? C11 C10 C7 122.08(13) . . ? C12 C11 C16 117.82(14) . . ? C12 C11 C10 121.70(13) . . ? C16 C11 C10 120.39(14) . . ? C13 C12 C11 121.83(14) . . ? C12 C13 C14 119.25(15) . . ? C15 C14 C13 120.52(15) . . ? C14 C15 C16 120.42(14) . . ? O2 C16 C15 117.80(14) . . ? O2 C16 C11 122.22(14) . . ? C15 C16 C11 119.99(14) . . ? 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 C6 C1 C2 O1 176.17(14) . . . . ? C7 C1 C2 O1 2.2(2) . . . . ? C6 C1 C2 C3 -2.8(2) . . . . ? C7 C1 C2 C3 -176.78(14) . . . . ? O1 C2 C3 C4 -177.19(14) . . . . ? C1 C2 C3 C4 1.9(2) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C3 C4 C5 C6 -1.3(2) . . . . ? C4 C5 C6 C1 0.2(2) . . . . ? C2 C1 C6 C5 1.8(2) . . . . ? C7 C1 C6 C5 175.69(14) . . . . ? C8 N1 C7 C1 168.58(14) . . . . ? C8 N1 C7 C10 -8.4(2) . . . . ? C6 C1 C7 N1 -157.31(15) . . . . ? C2 C1 C7 N1 16.4(2) . . . . ? C6 C1 C7 C10 19.5(2) . . . . ? C2 C1 C7 C10 -166.73(14) . . . . ? C7 N1 C8 C9 -36.3(2) . . . . ? C10 N2 C9 C8 -40.13(19) . . . . ? N1 C8 C9 N2 60.95(17) . . . . ? C9 N2 C10 C11 172.58(13) . . . . ? C9 N2 C10 C7 -4.8(2) . . . . ? N1 C7 C10 N2 32.8(2) . . . . ? C1 C7 C10 N2 -144.06(16) . . . . ? N1 C7 C10 C11 -144.53(16) . . . . ? C1 C7 C10 C11 38.6(2) . . . . ? N2 C10 C11 C12 -158.98(15) . . . . ? C7 C10 C11 C12 18.3(2) . . . . ? N2 C10 C11 C16 17.5(2) . . . . ? C7 C10 C11 C16 -165.27(15) . . . . ? C16 C11 C12 C13 2.9(2) . . . . ? C10 C11 C12 C13 179.44(13) . . . . ? C11 C12 C13 C14 0.7(2) . . . . ? C12 C13 C14 C15 -2.3(2) . . . . ? C13 C14 C15 C16 0.2(2) . . . . ? C14 C15 C16 O2 -176.40(14) . . . . ? C14 C15 C16 C11 3.5(2) . . . . ? C12 C11 C16 O2 174.91(13) . . . . ? C10 C11 C16 O2 -1.7(2) . . . . ? C12 C11 C16 C15 -5.0(2) . . . . ? C10 C11 C16 C15 178.47(13) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.506 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.086