# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Brian Jennings' _publ_contact_author_email WBJ@SKY.COM _publ_section_title ; Topically resolved intramolecular CH-? interactions in phenylalanine derivatives ; loop_ _publ_author_name 'Brian Jennings' 'Padraig Kelly' 'John F Malone' 'Noel J. P. McCarthy' # Attachment 'nitrone4.cif' data_nitrone4 _database_code_depnum_ccdc_archive 'CCDC 739741' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H21 N O3' _chemical_formula_sum 'C23 H21 N O3' _chemical_formula_weight 359.41 _chemical_absolute_configuration rm 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.729(2) _cell_length_b 10.168(2) _cell_length_c 18.965(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1876.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 979 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 24.98 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19868 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.40 _reflns_number_total 3843 _reflns_number_gt 3457 _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 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0513P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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(9) _refine_ls_number_reflns 3843 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0802 _refine_ls_wR_factor_gt 0.0779 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 C1 C 0.22650(13) 0.37661(12) 0.86237(7) 0.0266(3) Uani 1 1 d . . . N1 N 0.17639(11) 0.29782(10) 0.91123(5) 0.0261(2) Uani 1 1 d . . . O1 O 0.04702(9) 0.28365(9) 0.92451(5) 0.0327(2) Uani 1 1 d . . . C2 C 0.37487(13) 0.37488(13) 0.84301(7) 0.0285(3) Uani 1 1 d . . . C3 C 0.45220(15) 0.48937(15) 0.84941(7) 0.0364(3) Uani 1 1 d . . . H3 H 0.4107 0.5668 0.8676 0.044 Uiso 1 1 calc R . . C4 C 0.58935(17) 0.49147(18) 0.82949(8) 0.0450(4) Uani 1 1 d . . . H4 H 0.6417 0.5697 0.8349 0.054 Uiso 1 1 calc R . . C5 C 0.64994(16) 0.38042(19) 0.80181(8) 0.0479(4) Uani 1 1 d . . . H5 H 0.7443 0.3816 0.7889 0.057 Uiso 1 1 calc R . . C6 C 0.57301(16) 0.26722(17) 0.79279(7) 0.0437(4) Uani 1 1 d . . . H6 H 0.6141 0.1913 0.7726 0.052 Uiso 1 1 calc R . . C7 C 0.43612(16) 0.26408(14) 0.81316(7) 0.0355(3) Uani 1 1 d . . . H7 H 0.3838 0.1861 0.8067 0.043 Uiso 1 1 calc R . . C8 C 0.13553(13) 0.46810(12) 0.82373(7) 0.0265(3) Uani 1 1 d . . . C9 C 0.02970(15) 0.53659(14) 0.85744(8) 0.0342(3) Uani 1 1 d . . . H9 H 0.0097 0.5197 0.9056 0.041 Uiso 1 1 calc R . . C10 C -0.04602(16) 0.62913(15) 0.82043(8) 0.0397(3) Uani 1 1 d . . . H10 H -0.1160 0.6775 0.8438 0.041(4) Uiso 1 1 calc R . . C11 C -0.02046(16) 0.65161(14) 0.74967(8) 0.0401(4) Uani 1 1 d . . . H11 H -0.0739 0.7141 0.7245 0.048 Uiso 1 1 calc R . . C12 C 0.08251(16) 0.58341(15) 0.71567(8) 0.0389(3) Uani 1 1 d . . . H12 H 0.0990 0.5979 0.6669 0.047 Uiso 1 1 calc R . . C13 C 0.16190(14) 0.49370(13) 0.75263(7) 0.0325(3) Uani 1 1 d . . . H13 H 0.2349 0.4492 0.7294 0.039 Uiso 1 1 calc R . . C14 C 0.26543(14) 0.22548(12) 0.96194(7) 0.0277(3) Uani 1 1 d . . . H14 H 0.3641 0.2433 0.9507 0.033 Uiso 1 1 calc R . . C15 C 0.23392(14) 0.27313(12) 1.03693(6) 0.0284(3) Uani 1 1 d . . . H15A H 0.1432 0.2385 1.0516 0.034 Uiso 1 1 calc R . . H15B H 0.3039 0.2373 1.0696 0.034 Uiso 1 1 calc R . . C16 C 0.23266(14) 0.42103(13) 1.04268(6) 0.0306(3) Uani 1 1 d . . . C17 C 0.11536(16) 0.48576(15) 1.06637(8) 0.0414(4) Uani 1 1 d . . . H17 H 0.0370 0.4360 1.0799 0.050 Uiso 1 1 calc R . . C18 C 0.1114(2) 0.62166(17) 1.07050(10) 0.0542(5) Uani 1 1 d . . . H18 H 0.0305 0.6642 1.0869 0.065 Uiso 1 1 calc R . . C19 C 0.2226(2) 0.69503(16) 1.05116(9) 0.0543(5) Uani 1 1 d . . . H19 H 0.2189 0.7883 1.0533 0.065 Uiso 1 1 calc R . . C20 C 0.3403(2) 0.63263(17) 1.02854(9) 0.0520(5) Uani 1 1 d . . . H20 H 0.4180 0.6835 1.0152 0.062 Uiso 1 1 calc R . . C21 C 0.34679(17) 0.49621(15) 1.02495(8) 0.0402(4) Uani 1 1 d . . . H21 H 0.4293 0.4544 1.0104 0.048 Uiso 1 1 calc R . . C22 C 0.23756(15) 0.07890(13) 0.95563(7) 0.0334(3) Uani 1 1 d . . . O22 O 0.22849(18) 0.00744(11) 1.00499(6) 0.0650(4) Uani 1 1 d . . . O23 O 0.22842(12) 0.04002(9) 0.88908(5) 0.0413(3) Uani 1 1 d . . . C23 C 0.1960(2) -0.09751(15) 0.87739(9) 0.0502(4) Uani 1 1 d . . . H23A H 0.1132 -0.1208 0.9040 0.075 Uiso 1 1 calc R . . H23B H 0.2730 -0.1522 0.8932 0.075 Uiso 1 1 calc R . . H23C H 0.1799 -0.1125 0.8270 0.075 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 C1 0.0316(7) 0.0236(6) 0.0246(6) -0.0002(5) -0.0007(5) -0.0009(5) N1 0.0263(6) 0.0246(5) 0.0274(6) 0.0013(4) -0.0020(4) -0.0005(4) O1 0.0246(5) 0.0365(5) 0.0369(5) 0.0063(4) -0.0002(4) -0.0047(4) C2 0.0297(7) 0.0322(7) 0.0237(6) 0.0050(5) -0.0004(5) 0.0002(6) C3 0.0374(8) 0.0374(8) 0.0344(7) 0.0040(6) 0.0001(6) -0.0053(6) C4 0.0387(8) 0.0591(10) 0.0371(8) 0.0068(7) 0.0002(6) -0.0153(8) C5 0.0299(8) 0.0794(13) 0.0344(8) 0.0112(8) 0.0049(6) -0.0025(8) C6 0.0412(9) 0.0583(10) 0.0316(8) 0.0033(7) 0.0085(6) 0.0129(8) C7 0.0372(8) 0.0378(8) 0.0314(7) 0.0036(6) 0.0021(6) 0.0025(6) C8 0.0280(6) 0.0237(6) 0.0278(6) 0.0004(5) -0.0026(5) -0.0042(5) C9 0.0379(8) 0.0340(7) 0.0308(7) 0.0002(6) 0.0011(6) 0.0041(6) C10 0.0372(8) 0.0352(8) 0.0466(9) -0.0010(7) -0.0013(7) 0.0090(7) C11 0.0428(9) 0.0329(7) 0.0446(9) 0.0081(7) -0.0105(7) 0.0047(7) C12 0.0470(8) 0.0408(8) 0.0291(7) 0.0077(6) -0.0034(6) -0.0012(7) C13 0.0345(8) 0.0313(7) 0.0317(7) 0.0013(6) 0.0005(6) 0.0004(6) C14 0.0274(7) 0.0260(7) 0.0298(7) 0.0057(5) -0.0004(5) 0.0004(5) C15 0.0300(7) 0.0274(7) 0.0279(7) 0.0040(5) -0.0023(5) 0.0002(5) C16 0.0383(8) 0.0283(7) 0.0252(6) 0.0025(5) -0.0081(6) -0.0015(6) C17 0.0402(8) 0.0352(8) 0.0487(9) -0.0001(7) -0.0074(7) 0.0036(7) C18 0.0633(11) 0.0370(9) 0.0621(11) -0.0052(8) -0.0148(9) 0.0137(9) C19 0.0904(14) 0.0274(8) 0.0452(9) 0.0014(7) -0.0209(9) 0.0006(9) C20 0.0764(13) 0.0422(9) 0.0376(9) 0.0056(7) -0.0088(8) -0.0250(9) C21 0.0469(9) 0.0390(8) 0.0349(8) 0.0005(6) -0.0018(6) -0.0118(7) C22 0.0375(8) 0.0292(7) 0.0335(7) 0.0025(6) 0.0037(6) 0.0027(6) O22 0.1287(13) 0.0282(5) 0.0382(6) 0.0076(5) 0.0018(7) -0.0062(7) O23 0.0595(7) 0.0298(5) 0.0347(5) -0.0008(4) 0.0029(5) -0.0047(5) C23 0.0721(12) 0.0304(8) 0.0481(10) -0.0063(7) 0.0055(8) -0.0060(8) _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 C1 N1 1.3184(16) . ? C1 C8 1.4784(18) . ? C1 C2 1.4896(19) . ? N1 O1 1.2917(14) . ? N1 C14 1.4887(16) . ? C2 C3 1.391(2) . ? C2 C7 1.395(2) . ? C3 C4 1.387(2) . ? C3 H3 0.9500 . ? C4 C5 1.378(2) . ? C4 H4 0.9500 . ? C5 C6 1.384(2) . ? C5 H5 0.9500 . ? C6 C7 1.387(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.3970(18) . ? C8 C9 1.3978(19) . ? C9 C10 1.386(2) . ? C9 H9 0.9500 . ? C10 C11 1.384(2) . ? C10 H10 0.9500 . ? C11 C12 1.379(2) . ? C11 H11 0.9500 . ? C12 C13 1.386(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C22 1.5196(19) . ? C14 C15 1.5336(17) . ? C14 H14 1.0000 . ? C15 C16 1.5078(19) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C21 1.389(2) . ? C16 C17 1.392(2) . ? C17 C18 1.385(2) . ? C17 H17 0.9500 . ? C18 C19 1.365(3) . ? C18 H18 0.9500 . ? C19 C20 1.377(3) . ? C19 H19 0.9500 . ? C20 C21 1.390(2) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 O22 1.1882(16) . ? C22 O23 1.3257(17) . ? O23 C23 1.4506(18) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 N1 C1 C8 120.62(12) . . ? N1 C1 C2 121.63(12) . . ? C8 C1 C2 117.73(11) . . ? O1 N1 C1 124.42(11) . . ? O1 N1 C14 112.70(10) . . ? C1 N1 C14 122.62(11) . . ? C3 C2 C7 118.70(13) . . ? C3 C2 C1 119.52(13) . . ? C7 C2 C1 121.58(13) . . ? C4 C3 C2 120.62(15) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 120.19(15) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.83(14) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C7 120.27(15) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C2 120.32(15) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? C13 C8 C9 118.94(12) . . ? C13 C8 C1 119.06(12) . . ? C9 C8 C1 121.85(12) . . ? C10 C9 C8 119.88(13) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C11 C10 C9 120.52(14) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 120.08(13) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 119.97(13) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C8 120.57(13) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? N1 C14 C22 109.26(11) . . ? N1 C14 C15 109.07(10) . . ? C22 C14 C15 110.31(10) . . ? N1 C14 H14 109.4 . . ? C22 C14 H14 109.4 . . ? C15 C14 H14 109.4 . . ? C16 C15 C14 112.56(10) . . ? C16 C15 H15A 109.1 . . ? C14 C15 H15A 109.1 . . ? C16 C15 H15B 109.1 . . ? C14 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? C21 C16 C17 118.24(14) . . ? C21 C16 C15 121.65(13) . . ? C17 C16 C15 120.10(12) . . ? C18 C17 C16 120.88(16) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C19 C18 C17 120.53(17) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 119.42(15) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C19 C20 C21 120.84(17) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C16 C21 C20 120.05(17) . . ? C16 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? O22 C22 O23 124.24(13) . . ? O22 C22 C14 123.44(13) . . ? O23 C22 C14 112.29(11) . . ? C22 O23 C23 116.59(12) . . ? O23 C23 H23A 109.5 . . ? O23 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O23 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C8 C1 N1 O1 7.16(19) . . . . ? C2 C1 N1 O1 -171.47(12) . . . . ? C8 C1 N1 C14 -166.52(11) . . . . ? C2 C1 N1 C14 14.85(18) . . . . ? N1 C1 C2 C3 -121.64(14) . . . . ? C8 C1 C2 C3 59.69(17) . . . . ? N1 C1 C2 C7 63.62(18) . . . . ? C8 C1 C2 C7 -115.05(14) . . . . ? C7 C2 C3 C4 -2.9(2) . . . . ? C1 C2 C3 C4 -177.82(13) . . . . ? C2 C3 C4 C5 1.2(2) . . . . ? C3 C4 C5 C6 1.1(2) . . . . ? C4 C5 C6 C7 -1.6(2) . . . . ? C5 C6 C7 C2 -0.1(2) . . . . ? C3 C2 C7 C6 2.4(2) . . . . ? C1 C2 C7 C6 177.15(12) . . . . ? N1 C1 C8 C13 -144.46(13) . . . . ? C2 C1 C8 C13 34.22(17) . . . . ? N1 C1 C8 C9 40.00(18) . . . . ? C2 C1 C8 C9 -141.31(13) . . . . ? C13 C8 C9 C10 -0.7(2) . . . . ? C1 C8 C9 C10 174.87(13) . . . . ? C8 C9 C10 C11 1.9(2) . . . . ? C9 C10 C11 C12 -1.1(2) . . . . ? C10 C11 C12 C13 -1.0(2) . . . . ? C11 C12 C13 C8 2.2(2) . . . . ? C9 C8 C13 C12 -1.4(2) . . . . ? C1 C8 C13 C12 -177.08(13) . . . . ? O1 N1 C14 C22 63.00(13) . . . . ? C1 N1 C14 C22 -122.64(13) . . . . ? O1 N1 C14 C15 -57.65(13) . . . . ? C1 N1 C14 C15 116.70(13) . . . . ? N1 C14 C15 C16 -48.69(14) . . . . ? C22 C14 C15 C16 -168.70(11) . . . . ? C14 C15 C16 C21 -58.41(16) . . . . ? C14 C15 C16 C17 121.74(14) . . . . ? C21 C16 C17 C18 1.6(2) . . . . ? C15 C16 C17 C18 -178.56(14) . . . . ? C16 C17 C18 C19 0.2(3) . . . . ? C17 C18 C19 C20 -1.1(3) . . . . ? C18 C19 C20 C21 0.2(3) . . . . ? C17 C16 C21 C20 -2.4(2) . . . . ? C15 C16 C21 C20 177.73(13) . . . . ? C19 C20 C21 C16 1.5(2) . . . . ? N1 C14 C22 O22 -138.06(16) . . . . ? C15 C14 C22 O22 -18.2(2) . . . . ? N1 C14 C22 O23 43.66(15) . . . . ? C15 C14 C22 O23 163.55(11) . . . . ? O22 C22 O23 C23 4.3(2) . . . . ? C14 C22 O23 C23 -177.41(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.163 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.030 # Attachment 'nitrone6.cif' data_nitrone6 _database_code_depnum_ccdc_archive 'CCDC 739742' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H20 N2 O5' _chemical_formula_sum 'C23 H20 N2 O5' _chemical_formula_weight 404.41 _chemical_absolute_configuration rm 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.094(2) _cell_length_b 11.642(3) _cell_length_c 9.371(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.370(4) _cell_angle_gamma 90.00 _cell_volume 991.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 879 _cell_measurement_theta_min 3.16 _cell_measurement_theta_max 26.29 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.937 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8232 _diffrn_reflns_av_R_equivalents 0.0090 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3955 _reflns_number_gt 3698 _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 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0464P)^2^+0.0462P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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 0.3(7) _refine_ls_number_reflns 3955 _refine_ls_number_parameters 272 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0770 _refine_ls_wR_factor_gt 0.0752 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 C1 C 0.12183(14) 0.84798(11) 0.82632(14) 0.0241(3) Uani 1 1 d . . . N1 N 0.04176(12) 0.86532(10) 0.70900(11) 0.0259(2) Uani 1 1 d . . . 01 O 0.03607(11) 0.79749(9) 0.59988(10) 0.0348(2) Uani 1 1 d . . . C2 C 0.11120(14) 0.93091(11) 0.94625(14) 0.0253(3) Uani 1 1 d . . . C3 C 0.21300(17) 1.01891(13) 0.96168(16) 0.0348(3) Uani 1 1 d . . . H3 H 0.2888 1.0273 0.8945 0.042 Uiso 1 1 calc R . . C4 C 0.20396(19) 1.09456(15) 1.07515(17) 0.0424(4) Uani 1 1 d . . . H4 H 0.2724 1.1560 1.0838 0.051 Uiso 1 1 calc R . . C5 C 0.09687(18) 1.08190(14) 1.17583(16) 0.0387(4) Uani 1 1 d . . . H5 H 0.0921 1.1338 1.2538 0.046 Uiso 1 1 calc R . . C6 C -0.00342(17) 0.99320(14) 1.16238(16) 0.0364(3) Uani 1 1 d . . . H6 H -0.0768 0.9836 1.2318 0.044 Uiso 1 1 calc R . . C7 C 0.00286(16) 0.91823(13) 1.04779(14) 0.0317(3) Uani 1 1 d . . . H7 H -0.0670 0.8579 1.0384 0.038 Uiso 1 1 calc R . . C8 C 0.21888(14) 0.74729(11) 0.84430(14) 0.0258(3) Uani 1 1 d . . . C9 C 0.27201(14) 0.68200(12) 0.73170(14) 0.0280(3) Uani 1 1 d . . . H9 H 0.2460 0.7020 0.6361 0.034 Uiso 1 1 calc R . . C10 C 0.36265(15) 0.58805(13) 0.75840(16) 0.0316(3) Uani 1 1 d . . . H10 H 0.3996 0.5453 0.6807 0.038 Uiso 1 1 calc R . . C11 C 0.39962(17) 0.55606(13) 0.89616(17) 0.0360(3) Uani 1 1 d . . . H11 H 0.4597 0.4906 0.9135 0.043 Uiso 1 1 calc R . . C12 C 0.34866(17) 0.61992(13) 1.00887(16) 0.0375(4) Uani 1 1 d . . . H12 H 0.3741 0.5982 1.1040 0.045 Uiso 1 1 calc R . . C13 C 0.26077(17) 0.71540(13) 0.98436(15) 0.0332(3) Uani 1 1 d . . . H13 H 0.2285 0.7597 1.0627 0.040 Uiso 1 1 calc R . . C14 C -0.05411(15) 0.96904(11) 0.68846(15) 0.0276(3) Uani 1 1 d . . . H14 H -0.0524 1.0163 0.7776 0.033 Uiso 1 1 calc R . . C15 C 0.00023(17) 1.04078(13) 0.56391(15) 0.0339(3) Uani 1 1 d . . . H15A H 0.0078 0.9909 0.4788 0.041 Uiso 1 1 calc R . . H15B H -0.0731 1.1014 0.5413 0.041 Uiso 1 1 calc R . . C16 C 0.14699(16) 1.09614(13) 0.59410(14) 0.0309(3) Uani 1 1 d . . . C17 C 0.27620(17) 1.04275(13) 0.55494(16) 0.0347(3) Uani 1 1 d . . . H17 H 0.2715 0.9700 0.5092 0.042 Uiso 1 1 calc R . . C18 C 0.41199(17) 1.09342(13) 0.58125(15) 0.0350(3) Uani 1 1 d . . . H18 H 0.5002 1.0563 0.5544 0.042 Uiso 1 1 calc R . . C19 C 0.41568(16) 1.19981(13) 0.64793(16) 0.0318(3) Uani 1 1 d . . . N19 N 0.55873(15) 1.25639(11) 0.67101(14) 0.0381(3) Uani 1 1 d . . . 019 O 0.67078(13) 1.20312(11) 0.64276(14) 0.0522(3) Uani 1 1 d . . . O20 O 0.56092(14) 1.35364(11) 0.71872(17) 0.0604(4) Uani 1 1 d . . . C20 C 0.28949(17) 1.25540(13) 0.68848(17) 0.0357(3) Uani 1 1 d . . . H20 H 0.2947 1.3282 0.7341 0.043 Uiso 1 1 calc R . . C21 C 0.15511(16) 1.20294(13) 0.66128(16) 0.0345(3) Uani 1 1 d . . . H21 H 0.0672 1.2402 0.6887 0.041 Uiso 1 1 calc R . . C22 C -0.20939(16) 0.92507(12) 0.65765(15) 0.0303(3) Uani 1 1 d . . . 022 O -0.27739(12) 0.94003(10) 0.54844(11) 0.0403(3) Uani 1 1 d . . . 023 O -0.26120(11) 0.87125(10) 0.77164(11) 0.0390(3) Uani 1 1 d . . . C23 C -0.40921(18) 0.82658(17) 0.7540(2) 0.0538(5) Uani 1 1 d . . . H23A H -0.4743 0.8873 0.7171 0.081 Uiso 1 1 calc R . . H23B H -0.4442 0.7999 0.8463 0.081 Uiso 1 1 calc R . . H23C H -0.4092 0.7623 0.6865 0.081 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 C1 0.0251(6) 0.0235(6) 0.0238(6) 0.0000(5) 0.0003(5) -0.0020(5) N1 0.0303(6) 0.0240(6) 0.0234(5) -0.0011(5) -0.0014(4) 0.0016(5) 01 0.0440(6) 0.0336(5) 0.0262(5) -0.0092(4) -0.0093(4) 0.0072(5) C2 0.0283(7) 0.0243(6) 0.0230(6) 0.0007(5) -0.0045(5) 0.0031(5) C3 0.0348(8) 0.0364(8) 0.0332(8) -0.0041(6) 0.0008(6) -0.0049(6) C4 0.0484(9) 0.0352(8) 0.0433(9) -0.0104(7) -0.0065(7) -0.0075(7) C5 0.0464(9) 0.0367(8) 0.0325(8) -0.0125(6) -0.0071(6) 0.0109(7) C6 0.0351(8) 0.0457(9) 0.0286(8) -0.0046(7) 0.0017(6) 0.0086(7) C7 0.0308(7) 0.0345(7) 0.0298(7) -0.0009(6) -0.0011(6) 0.0005(6) C8 0.0254(6) 0.0255(6) 0.0265(7) -0.0009(5) -0.0021(5) -0.0021(5) C9 0.0279(7) 0.0283(7) 0.0279(7) -0.0018(6) 0.0004(5) -0.0030(5) C10 0.0294(7) 0.0297(7) 0.0357(8) -0.0061(6) 0.0014(5) 0.0005(6) C11 0.0357(8) 0.0281(7) 0.0438(8) -0.0015(7) -0.0060(6) 0.0065(6) C12 0.0446(9) 0.0349(8) 0.0324(8) 0.0007(7) -0.0087(7) 0.0076(7) C13 0.0394(8) 0.0317(7) 0.0283(7) -0.0034(6) -0.0041(6) 0.0074(6) C14 0.0313(7) 0.0243(7) 0.0271(7) 0.0005(5) -0.0031(5) 0.0050(5) C15 0.0387(8) 0.0330(7) 0.0297(7) 0.0063(6) -0.0037(6) 0.0032(6) C16 0.0385(8) 0.0304(7) 0.0239(7) 0.0081(6) -0.0010(5) 0.0011(6) C17 0.0455(9) 0.0288(7) 0.0297(7) -0.0004(6) 0.0022(6) 0.0033(6) C18 0.0404(8) 0.0339(8) 0.0311(7) 0.0026(6) 0.0071(6) 0.0071(7) C19 0.0374(8) 0.0288(7) 0.0292(7) 0.0079(6) 0.0038(6) 0.0005(6) N19 0.0405(7) 0.0364(7) 0.0376(7) 0.0056(6) 0.0055(6) -0.0004(6) 019 0.0375(6) 0.0586(8) 0.0612(8) -0.0097(7) 0.0158(5) -0.0016(6) O20 0.0493(7) 0.0372(7) 0.0945(11) -0.0113(7) -0.0043(7) -0.0023(6) C20 0.0419(8) 0.0245(7) 0.0407(8) -0.0001(6) 0.0023(6) 0.0027(6) C21 0.0364(8) 0.0301(7) 0.0372(8) 0.0040(6) 0.0033(6) 0.0077(6) C22 0.0317(7) 0.0242(6) 0.0347(8) -0.0032(6) -0.0037(6) 0.0044(6) 022 0.0376(6) 0.0450(6) 0.0377(6) -0.0012(5) -0.0110(5) 0.0061(5) 023 0.0328(5) 0.0380(6) 0.0459(6) 0.0111(5) -0.0068(4) -0.0046(5) C23 0.0327(8) 0.0497(11) 0.0782(13) 0.0244(9) -0.0118(8) -0.0103(7) _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 C1 N1 1.3197(17) . ? C1 C8 1.4746(19) . ? C1 C2 1.4865(18) . ? N1 01 1.2921(15) . ? N1 C14 1.4991(17) . ? C2 C3 1.386(2) . ? C2 C7 1.394(2) . ? C3 C4 1.385(2) . ? C3 H3 0.9500 . ? C4 C5 1.380(2) . ? C4 H4 0.9500 . ? C5 C6 1.382(2) . ? C5 H5 0.9500 . ? C6 C7 1.386(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.3961(19) . ? C8 C13 1.408(2) . ? C9 C10 1.389(2) . ? C9 H9 0.9500 . ? C10 C11 1.378(2) . ? C10 H10 0.9500 . ? C11 C12 1.381(2) . ? C11 H11 0.9500 . ? C12 C13 1.385(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C22 1.5231(19) . ? C14 C15 1.527(2) . ? C14 H14 1.0000 . ? C15 C16 1.503(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.386(2) . ? C16 C21 1.395(2) . ? C17 C18 1.385(2) . ? C17 H17 0.9500 . ? C18 C19 1.387(2) . ? C18 H18 0.9500 . ? C19 C20 1.379(2) . ? C19 N19 1.470(2) . ? N19 O20 1.2172(18) . ? N19 019 1.2271(18) . ? C20 C21 1.384(2) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 022 1.1958(17) . ? C22 023 1.3341(18) . ? 023 C23 1.4487(19) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 N1 C1 C8 122.25(11) . . ? N1 C1 C2 119.08(11) . . ? C8 C1 C2 118.65(11) . . ? 01 N1 C1 125.22(11) . . ? 01 N1 C14 112.24(10) . . ? C1 N1 C14 122.53(11) . . ? C3 C2 C7 119.23(13) . . ? C3 C2 C1 120.24(12) . . ? C7 C2 C1 120.48(12) . . ? C4 C3 C2 119.90(14) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.86(15) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 119.51(14) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C7 120.13(15) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C2 120.34(14) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? C9 C8 C13 118.05(12) . . ? C9 C8 C1 124.30(12) . . ? C13 C8 C1 117.65(12) . . ? C10 C9 C8 120.48(12) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 120.82(13) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 119.50(13) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 120.54(13) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 120.57(13) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? N1 C14 C22 106.69(11) . . ? N1 C14 C15 109.93(11) . . ? C22 C14 C15 110.76(11) . . ? N1 C14 H14 109.8 . . ? C22 C14 H14 109.8 . . ? C15 C14 H14 109.8 . . ? C16 C15 C14 113.13(11) . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C17 C16 C21 118.89(14) . . ? C17 C16 C15 120.81(14) . . ? C21 C16 C15 120.30(13) . . ? C18 C17 C16 121.30(14) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C19 118.18(14) . . ? C17 C18 H18 120.9 . . ? C19 C18 H18 120.9 . . ? C20 C19 C18 122.13(14) . . ? C20 C19 N19 119.26(13) . . ? C18 C19 N19 118.57(13) . . ? O20 N19 019 122.88(14) . . ? O20 N19 C19 118.53(13) . . ? 019 N19 C19 118.58(13) . . ? C19 C20 C21 118.62(14) . . ? C19 C20 H20 120.7 . . ? C21 C20 H20 120.7 . . ? C20 C21 C16 120.88(14) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? 022 C22 023 124.64(14) . . ? 022 C22 C14 124.84(14) . . ? 023 C22 C14 110.47(11) . . ? C22 023 C23 114.95(12) . . ? 023 C23 H23A 109.5 . . ? 023 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? 023 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C8 C1 N1 01 1.4(2) . . . . ? C2 C1 N1 01 -176.89(12) . . . . ? C8 C1 N1 C14 -178.36(12) . . . . ? C2 C1 N1 C14 3.30(18) . . . . ? N1 C1 C2 C3 -96.30(16) . . . . ? C8 C1 C2 C3 85.30(16) . . . . ? N1 C1 C2 C7 86.47(16) . . . . ? C8 C1 C2 C7 -91.93(16) . . . . ? C7 C2 C3 C4 -1.6(2) . . . . ? C1 C2 C3 C4 -178.82(14) . . . . ? C2 C3 C4 C5 1.7(2) . . . . ? C3 C4 C5 C6 -0.6(2) . . . . ? C4 C5 C6 C7 -0.6(2) . . . . ? C5 C6 C7 C2 0.7(2) . . . . ? C3 C2 C7 C6 0.4(2) . . . . ? C1 C2 C7 C6 177.62(13) . . . . ? N1 C1 C8 C9 20.8(2) . . . . ? C2 C1 C8 C9 -160.84(12) . . . . ? N1 C1 C8 C13 -159.38(13) . . . . ? C2 C1 C8 C13 18.97(18) . . . . ? C13 C8 C9 C10 0.4(2) . . . . ? C1 C8 C9 C10 -179.76(13) . . . . ? C8 C9 C10 C11 1.3(2) . . . . ? C9 C10 C11 C12 -1.5(2) . . . . ? C10 C11 C12 C13 0.1(2) . . . . ? C11 C12 C13 C8 1.6(2) . . . . ? C9 C8 C13 C12 -1.8(2) . . . . ? C1 C8 C13 C12 178.33(14) . . . . ? 01 N1 C14 C22 56.94(14) . . . . ? C1 N1 C14 C22 -123.23(13) . . . . ? 01 N1 C14 C15 -63.22(14) . . . . ? C1 N1 C14 C15 116.61(14) . . . . ? N1 C14 C15 C16 -68.01(15) . . . . ? C22 C14 C15 C16 174.33(12) . . . . ? C14 C15 C16 C17 93.46(16) . . . . ? C14 C15 C16 C21 -87.04(16) . . . . ? C21 C16 C17 C18 0.0(2) . . . . ? C15 C16 C17 C18 179.49(13) . . . . ? C16 C17 C18 C19 -0.1(2) . . . . ? C17 C18 C19 C20 0.2(2) . . . . ? C17 C18 C19 N19 -177.54(13) . . . . ? C20 C19 N19 O20 -3.8(2) . . . . ? C18 C19 N19 O20 174.04(15) . . . . ? C20 C19 N19 019 175.49(14) . . . . ? C18 C19 N19 019 -6.7(2) . . . . ? C18 C19 C20 C21 -0.1(2) . . . . ? N19 C19 C20 C21 177.64(13) . . . . ? C19 C20 C21 C16 -0.1(2) . . . . ? C17 C16 C21 C20 0.1(2) . . . . ? C15 C16 C21 C20 -179.37(13) . . . . ? N1 C14 C22 022 -116.47(15) . . . . ? C15 C14 C22 022 3.16(19) . . . . ? N1 C14 C22 023 65.92(14) . . . . ? C15 C14 C22 023 -174.46(12) . . . . ? 022 C22 023 C23 2.0(2) . . . . ? C14 C22 023 C23 179.59(13) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.125 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.032 # Attachment 'imine2.cif' data_imine2 _database_code_depnum_ccdc_archive 'CCDC 739743' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H21 N O3' _chemical_formula_sum 'C23 H21 N O3' _chemical_formula_weight 359.41 _chemical_absolute_configuration rm 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.212(2) _cell_length_b 10.822(3) _cell_length_c 19.309(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1924.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 997 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 24.90 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.946 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20500 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 26.42 _reflns_number_total 3936 _reflns_number_gt 3447 _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 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0496P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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 -0.5(9) _refine_ls_number_reflns 3936 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0851 _refine_ls_wR_factor_gt 0.0824 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 C1 C 0.04287(15) -0.20932(13) 0.87906(7) 0.0282(3) Uani 1 1 d . . . N1 N 0.08001(13) -0.09534(11) 0.87465(6) 0.0308(3) Uani 1 1 d . . . C2 C 0.14528(15) -0.31699(13) 0.88565(7) 0.0292(3) Uani 1 1 d . . . C3 C 0.17869(16) -0.38851(14) 0.82851(8) 0.0320(3) Uani 1 1 d . . . H3 H 0.1403 -0.3674 0.7844 0.038 Uiso 1 1 calc R . . C4 C 0.26790(16) -0.49073(14) 0.83536(9) 0.0383(4) Uani 1 1 d . . . H4 H 0.2913 -0.5392 0.7959 0.046 Uiso 1 1 calc R . . C5 C 0.32288(19) -0.52229(15) 0.89942(10) 0.0444(4) Uani 1 1 d . . . H5 H 0.3825 -0.5934 0.9042 0.053 Uiso 1 1 calc R . . C6 C 0.2912(2) -0.45043(17) 0.95662(9) 0.0483(4) Uani 1 1 d . . . H6 H 0.3303 -0.4713 1.0006 0.058 Uiso 1 1 calc R . . C7 C 0.20240(17) -0.34806(15) 0.94971(8) 0.0399(4) Uani 1 1 d . . . H7 H 0.1805 -0.2988 0.9891 0.048 Uiso 1 1 calc R . . C8 C -0.11474(16) -0.23857(14) 0.87664(7) 0.0312(3) Uani 1 1 d . . . C9 C -0.21449(16) -0.14723(15) 0.85731(8) 0.0362(4) Uani 1 1 d . . . H9 H -0.1810 -0.0667 0.8461 0.043 Uiso 1 1 calc R . . C10 C -0.36093(17) -0.17325(16) 0.85443(9) 0.0429(4) Uani 1 1 d . . . H10 H -0.4275 -0.1103 0.8415 0.052 Uiso 1 1 calc R . . C11 C -0.41175(19) -0.29039(16) 0.87024(9) 0.0464(4) Uani 1 1 d . . . H11 H -0.5126 -0.3082 0.8680 0.056 Uiso 1 1 calc R . . C12 C -0.31390(18) -0.38107(16) 0.88935(10) 0.0465(4) Uani 1 1 d . . . H12 H -0.3478 -0.4616 0.9004 0.056 Uiso 1 1 calc R . . C13 C -0.16704(18) -0.35527(14) 0.89244(9) 0.0392(4) Uani 1 1 d . . . H13 H -0.1010 -0.4185 0.9056 0.047 Uiso 1 1 calc R . . C14 C 0.23222(15) -0.06209(13) 0.86918(7) 0.0305(3) Uani 1 1 d . . . H14 H 0.2954 -0.1353 0.8786 0.037 Uiso 1 1 calc R . . C15 C 0.25978(18) -0.01119(14) 0.79484(7) 0.0349(3) Uani 1 1 d . . . H15A H 0.1990 0.0631 0.7874 0.042 Uiso 1 1 calc R . . H15B H 0.3628 0.0139 0.7906 0.042 Uiso 1 1 calc R . . C16 C 0.22535(17) -0.10579(14) 0.73971(7) 0.0321(3) Uani 1 1 d . . . C17 C 0.08389(17) -0.12166(14) 0.71688(7) 0.0327(3) Uani 1 1 d . . . H17 H 0.0092 -0.0713 0.7358 0.039 Uiso 1 1 calc R . . C18 C 0.04875(17) -0.20891(14) 0.66732(7) 0.0333(3) Uani 1 1 d . . . H18 H -0.0491 -0.2181 0.6526 0.040 Uiso 1 1 calc R . . C19 C 0.15605(17) -0.28265(13) 0.63921(7) 0.0327(3) Uani 1 1 d . . . O19 O 0.12954(12) -0.36839(10) 0.58900(5) 0.0405(3) Uani 1 1 d . . . H19 H 0.0400 -0.3825 0.5869 0.061 Uiso 1 1 calc R . . C20 C 0.29900(17) -0.26848(15) 0.66149(8) 0.0375(4) Uani 1 1 d . . . H20 H 0.3734 -0.3190 0.6426 0.045 Uiso 1 1 calc R . . C21 C 0.33253(17) -0.18092(15) 0.71109(8) 0.0361(4) Uani 1 1 d . . . H21 H 0.4303 -0.1718 0.7259 0.043 Uiso 1 1 calc R . . C22 C 0.26331(18) 0.04075(14) 0.92040(7) 0.0330(3) Uani 1 1 d . . . O22 O 0.17512(13) 0.11297(11) 0.94215(6) 0.0464(3) Uani 1 1 d . . . O23 O 0.40350(12) 0.04253(11) 0.93688(5) 0.0411(3) Uani 1 1 d . . . C23 C 0.4477(2) 0.13698(16) 0.98600(9) 0.0491(4) Uani 1 1 d . . . H23A H 0.3940 0.1263 1.0294 0.074 Uiso 1 1 calc R . . H23B H 0.4270 0.2189 0.9667 0.074 Uiso 1 1 calc R . . H23C H 0.5521 0.1295 0.9950 0.074 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 C1 0.0327(8) 0.0289(8) 0.0232(7) -0.0009(6) -0.0004(6) 0.0007(6) N1 0.0324(6) 0.0301(7) 0.0299(6) -0.0019(5) -0.0014(5) 0.0003(5) C2 0.0292(7) 0.0255(7) 0.0330(7) 0.0034(6) 0.0004(6) -0.0025(6) C3 0.0333(8) 0.0285(7) 0.0342(7) 0.0003(6) -0.0034(6) -0.0028(6) C4 0.0341(8) 0.0300(8) 0.0508(9) -0.0035(7) 0.0019(7) -0.0001(7) C5 0.0407(9) 0.0298(8) 0.0626(11) 0.0123(8) -0.0024(8) 0.0055(7) C6 0.0545(11) 0.0491(10) 0.0412(9) 0.0176(8) -0.0055(8) 0.0056(9) C7 0.0470(10) 0.0413(9) 0.0314(8) 0.0055(7) -0.0008(7) 0.0033(8) C8 0.0343(8) 0.0299(8) 0.0292(7) -0.0042(6) 0.0012(6) 0.0004(6) C9 0.0350(8) 0.0346(8) 0.0391(8) 0.0001(7) -0.0026(7) 0.0001(7) C10 0.0352(9) 0.0437(10) 0.0499(9) -0.0017(8) -0.0051(7) 0.0044(7) C11 0.0309(8) 0.0485(11) 0.0599(11) -0.0096(9) 0.0017(8) -0.0028(8) C12 0.0406(9) 0.0359(9) 0.0632(11) -0.0069(9) 0.0079(8) -0.0073(8) C13 0.0371(8) 0.0320(8) 0.0485(9) -0.0011(7) 0.0052(7) 0.0019(7) C14 0.0326(8) 0.0276(7) 0.0312(7) -0.0004(6) -0.0040(6) 0.0013(6) C15 0.0400(9) 0.0308(8) 0.0339(8) 0.0008(6) -0.0026(7) -0.0042(7) C16 0.0392(8) 0.0297(7) 0.0274(7) 0.0042(6) -0.0015(6) -0.0017(7) C17 0.0374(8) 0.0305(8) 0.0302(7) 0.0014(6) -0.0016(6) 0.0061(7) C18 0.0359(8) 0.0348(8) 0.0294(7) 0.0034(6) -0.0040(6) 0.0007(7) C19 0.0445(9) 0.0274(8) 0.0262(7) 0.0015(6) 0.0014(6) -0.0026(7) O19 0.0503(7) 0.0345(6) 0.0369(6) -0.0082(5) 0.0035(5) -0.0045(5) C20 0.0385(9) 0.0383(9) 0.0357(8) -0.0010(7) 0.0073(7) 0.0038(7) C21 0.0325(8) 0.0407(9) 0.0351(8) 0.0001(7) 0.0006(6) -0.0037(7) C22 0.0404(9) 0.0287(8) 0.0298(7) 0.0031(6) -0.0038(7) 0.0000(7) O22 0.0511(7) 0.0386(6) 0.0493(7) -0.0116(6) -0.0095(6) 0.0089(6) O23 0.0415(6) 0.0427(7) 0.0391(6) -0.0092(5) -0.0094(5) -0.0028(5) C23 0.0621(11) 0.0426(10) 0.0427(9) -0.0085(8) -0.0156(8) -0.0076(9) _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 C1 N1 1.2829(19) . ? C1 C8 1.487(2) . ? C1 C2 1.505(2) . ? N1 C14 1.4514(19) . ? C2 C3 1.382(2) . ? C2 C7 1.386(2) . ? C3 C4 1.384(2) . ? C3 H3 0.9500 . ? C4 C5 1.379(2) . ? C4 H4 0.9500 . ? C5 C6 1.382(3) . ? C5 H5 0.9500 . ? C6 C7 1.383(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.386(2) . ? C8 C9 1.400(2) . ? C9 C10 1.379(2) . ? C9 H9 0.9500 . ? C10 C11 1.385(2) . ? C10 H10 0.9500 . ? C11 C12 1.383(3) . ? C11 H11 0.9500 . ? C12 C13 1.383(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C22 1.516(2) . ? C14 C15 1.558(2) . ? C14 H14 1.0000 . ? C15 C16 1.511(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.386(2) . ? C16 C21 1.393(2) . ? C17 C18 1.383(2) . ? C17 H17 0.9500 . ? C18 C19 1.381(2) . ? C18 H18 0.9500 . ? C19 O19 1.3641(17) . ? C19 C20 1.394(2) . ? O19 H19 0.8400 . ? C20 C21 1.382(2) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 O22 1.2030(19) . ? C22 O23 1.3302(19) . ? O23 C23 1.4527(18) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 N1 C1 C8 117.59(13) . . ? N1 C1 C2 125.66(13) . . ? C8 C1 C2 116.75(12) . . ? C1 N1 C14 120.05(13) . . ? C3 C2 C7 119.48(14) . . ? C3 C2 C1 120.37(12) . . ? C7 C2 C1 120.10(13) . . ? C2 C3 C4 120.21(14) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 120.10(15) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.98(15) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C7 119.89(15) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C6 C7 C2 120.32(16) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? C13 C8 C9 118.28(14) . . ? C13 C8 C1 121.78(14) . . ? C9 C8 C1 119.93(13) . . ? C10 C9 C8 120.56(15) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 120.56(16) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 119.21(16) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C13 120.40(16) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C8 120.98(16) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? N1 C14 C22 108.48(12) . . ? N1 C14 C15 108.18(12) . . ? C22 C14 C15 108.09(12) . . ? N1 C14 H14 110.7 . . ? C22 C14 H14 110.7 . . ? C15 C14 H14 110.7 . . ? C16 C15 C14 112.05(12) . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C21 117.89(14) . . ? C17 C16 C15 120.36(14) . . ? C21 C16 C15 121.74(14) . . ? C18 C17 C16 121.64(14) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C19 C18 C17 119.92(14) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? O19 C19 C18 122.96(14) . . ? O19 C19 C20 117.60(14) . . ? C18 C19 C20 119.42(14) . . ? C19 O19 H19 109.5 . . ? C21 C20 C19 120.03(14) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C16 121.09(15) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? O22 C22 O23 124.25(14) . . ? O22 C22 C14 125.24(14) . . ? O23 C22 C14 110.49(13) . . ? C22 O23 C23 116.02(13) . . ? O23 C23 H23A 109.5 . . ? O23 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O23 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C8 C1 N1 C14 -173.35(11) . . . . ? C2 C1 N1 C14 5.9(2) . . . . ? N1 C1 C2 C3 -100.79(17) . . . . ? C8 C1 C2 C3 78.44(17) . . . . ? N1 C1 C2 C7 81.73(19) . . . . ? C8 C1 C2 C7 -99.04(16) . . . . ? C7 C2 C3 C4 0.3(2) . . . . ? C1 C2 C3 C4 -177.16(13) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C3 C4 C5 C6 -1.3(2) . . . . ? C4 C5 C6 C7 1.1(3) . . . . ? C5 C6 C7 C2 -0.2(3) . . . . ? C3 C2 C7 C6 -0.5(2) . . . . ? C1 C2 C7 C6 176.96(14) . . . . ? N1 C1 C8 C13 -169.06(14) . . . . ? C2 C1 C8 C13 11.65(19) . . . . ? N1 C1 C8 C9 11.6(2) . . . . ? C2 C1 C8 C9 -167.69(13) . . . . ? C13 C8 C9 C10 0.2(2) . . . . ? C1 C8 C9 C10 179.60(14) . . . . ? C8 C9 C10 C11 -0.4(3) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C10 C11 C12 C13 -0.2(3) . . . . ? C11 C12 C13 C8 0.1(3) . . . . ? C9 C8 C13 C12 -0.1(2) . . . . ? C1 C8 C13 C12 -179.45(16) . . . . ? C1 N1 C14 C22 -132.46(14) . . . . ? C1 N1 C14 C15 110.51(14) . . . . ? N1 C14 C15 C16 -60.27(16) . . . . ? C22 C14 C15 C16 -177.55(12) . . . . ? C14 C15 C16 C17 83.27(17) . . . . ? C14 C15 C16 C21 -95.61(17) . . . . ? C21 C16 C17 C18 0.0(2) . . . . ? C15 C16 C17 C18 -178.91(13) . . . . ? C16 C17 C18 C19 -0.2(2) . . . . ? C17 C18 C19 O19 -178.38(13) . . . . ? C17 C18 C19 C20 0.3(2) . . . . ? O19 C19 C20 C21 178.48(14) . . . . ? C18 C19 C20 C21 -0.3(2) . . . . ? C19 C20 C21 C16 0.1(2) . . . . ? C17 C16 C21 C20 0.0(2) . . . . ? C15 C16 C21 C20 178.92(14) . . . . ? N1 C14 C22 O22 -25.4(2) . . . . ? C15 C14 C22 O22 91.68(18) . . . . ? N1 C14 C22 O23 156.24(12) . . . . ? C15 C14 C22 O23 -86.68(15) . . . . ? O22 C22 O23 C23 1.8(2) . . . . ? C14 C22 O23 C23 -179.79(12) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.150 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.030