# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Youhong Hu' _publ_contact_author_email yhhu@mail.shcnc.ac.cn _publ_author_name 'Youhong Hu' # Attachment '- cd29368.cif' data_cd29368 _database_code_depnum_ccdc_archive 'CCDC 755402' #TrackingRef '- cd29368.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H15 N O2' _chemical_formula_weight 361.38 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)/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 12.6312(12) _cell_length_b 12.1657(12) _cell_length_c 12.2949(12) _cell_angle_alpha 90.00 _cell_angle_beta 109.240(2) _cell_angle_gamma 90.00 _cell_volume 1783.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3490 _cell_measurement_theta_min 4.783 _cell_measurement_theta_max 53.796 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.422 _exptl_crystal_size_mid 0.369 _exptl_crystal_size_min 0.311 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.79183 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _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 '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 9222 _diffrn_reflns_av_R_equivalents 0.1142 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3301 _reflns_number_gt 2618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0752P)^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 SHELXL _refine_ls_extinction_coef 0.027(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3301 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1443 _refine_ls_wR_factor_gt 0.1374 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 N1 N 0.43346(13) 0.66051(14) 0.59659(13) 0.0553(4) Uani 1 1 d . . . O1 O 0.41999(11) 1.07635(10) 0.38166(10) 0.0586(4) Uani 1 1 d . . . O2 O 0.19692(8) 0.95211(9) 0.08944(9) 0.0397(3) Uani 1 1 d . . . C1 C 0.35912(13) 1.03615(13) 0.29136(14) 0.0381(4) Uani 1 1 d . . . C2 C 0.33144(12) 1.09235(13) 0.18009(13) 0.0358(4) Uani 1 1 d . . . C3 C 0.38351(14) 1.19092(13) 0.16701(16) 0.0434(4) Uani 1 1 d . . . H3 H 0.4348 1.2241 0.2309 0.052 Uiso 1 1 calc R . . C4 C 0.35933(14) 1.23858(15) 0.06075(15) 0.0468(4) Uani 1 1 d . . . H4 H 0.3950 1.3035 0.0527 0.056 Uiso 1 1 calc R . . C5 C 0.28195(17) 1.19056(15) -0.03486(17) 0.0537(5) Uani 1 1 d . . . H5 H 0.2662 1.2234 -0.1068 0.064 Uiso 1 1 calc R . . C6 C 0.22837(15) 1.09500(15) -0.02449(15) 0.0495(5) Uani 1 1 d . . . H6 H 0.1759 1.0631 -0.0885 0.059 Uiso 1 1 calc R . . C7 C 0.25412(13) 1.04706(13) 0.08329(13) 0.0371(4) Uani 1 1 d . . . C8 C 0.22761(12) 0.89402(13) 0.18928(13) 0.0340(4) Uani 1 1 d . . . C9 C 0.30899(12) 0.92640(12) 0.28633(12) 0.0331(4) Uani 1 1 d . . . C10 C 0.34660(12) 0.85895(13) 0.38866(13) 0.0347(4) Uani 1 1 d . . . H10 H 0.3741 0.8963 0.4584 0.042 Uiso 1 1 calc R . . C11 C 0.34651(12) 0.74824(14) 0.39502(12) 0.0345(4) Uani 1 1 d . . . C12 C 0.31482(12) 0.66875(13) 0.29921(13) 0.0351(4) Uani 1 1 d . . . C13 C 0.37223(13) 0.56907(14) 0.31162(16) 0.0442(4) Uani 1 1 d . . . H13 H 0.4245 0.5511 0.3826 0.053 Uiso 1 1 calc R . . C14 C 0.35313(15) 0.49686(14) 0.22126(17) 0.0497(5) Uani 1 1 d . . . H14 H 0.3924 0.4309 0.2313 0.060 Uiso 1 1 calc R . . C15 C 0.27602(14) 0.52206(15) 0.11612(16) 0.0487(5) Uani 1 1 d . . . H15 H 0.2643 0.4742 0.0542 0.058 Uiso 1 1 calc R . . C16 C 0.21582(14) 0.61893(14) 0.10272(15) 0.0431(4) Uani 1 1 d . . . H16 H 0.1633 0.6355 0.0315 0.052 Uiso 1 1 calc R . . C17 C 0.23215(13) 0.69177(12) 0.19326(14) 0.0351(4) Uani 1 1 d . . . C18 C 0.15795(13) 0.79196(13) 0.17729(14) 0.0368(4) Uani 1 1 d . . . H18 H 0.1079 0.7902 0.0972 0.044 Uiso 1 1 calc R . . C19 C 0.08221(12) 0.79303(13) 0.25199(14) 0.0386(4) Uani 1 1 d . . . C20 C 0.03878(14) 0.88955(16) 0.27749(16) 0.0514(5) Uani 1 1 d . . . H20 H 0.0616 0.9561 0.2554 0.062 Uiso 1 1 calc R . . C21 C -0.03816(16) 0.88919(18) 0.33539(18) 0.0633(6) Uani 1 1 d . . . H21 H -0.0671 0.9554 0.3509 0.076 Uiso 1 1 calc R . . C22 C -0.07234(16) 0.79244(19) 0.37022(19) 0.0639(6) Uani 1 1 d . . . H22 H -0.1260 0.7922 0.4069 0.077 Uiso 1 1 calc R . . C23 C -0.02615(18) 0.69636(18) 0.3500(2) 0.0703(7) Uani 1 1 d . . . H23 H -0.0458 0.6304 0.3765 0.084 Uiso 1 1 calc R . . C24 C 0.04956(17) 0.69616(16) 0.29060(19) 0.0599(6) Uani 1 1 d . . . H24 H 0.0791 0.6298 0.2763 0.072 Uiso 1 1 calc R . . C25 C 0.39541(13) 0.70084(14) 0.50833(15) 0.0403(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 N1 0.0600(10) 0.0542(10) 0.0489(10) 0.0121(8) 0.0139(8) -0.0024(7) O1 0.0764(9) 0.0422(8) 0.0458(7) -0.0054(6) 0.0045(6) -0.0160(6) O2 0.0402(6) 0.0363(6) 0.0388(6) 0.0035(5) 0.0080(5) -0.0021(5) C1 0.0379(8) 0.0335(9) 0.0439(9) -0.0032(7) 0.0148(7) 0.0020(7) C2 0.0347(8) 0.0306(9) 0.0450(9) -0.0002(7) 0.0170(7) 0.0053(6) C3 0.0412(9) 0.0326(9) 0.0588(11) -0.0016(8) 0.0198(8) 0.0017(7) C4 0.0486(10) 0.0345(9) 0.0644(11) 0.0067(9) 0.0283(8) 0.0020(8) C5 0.0652(12) 0.0479(12) 0.0535(11) 0.0146(9) 0.0268(10) 0.0084(9) C6 0.0567(11) 0.0470(11) 0.0429(10) 0.0043(8) 0.0138(8) 0.0023(8) C7 0.0369(8) 0.0320(9) 0.0450(9) 0.0023(7) 0.0170(7) 0.0043(7) C8 0.0328(8) 0.0334(8) 0.0371(8) 0.0012(7) 0.0133(6) 0.0040(6) C9 0.0340(8) 0.0298(8) 0.0377(8) -0.0027(6) 0.0145(6) 0.0019(6) C10 0.0313(8) 0.0387(9) 0.0355(8) -0.0034(7) 0.0127(6) -0.0011(6) C11 0.0292(8) 0.0366(9) 0.0385(8) 0.0024(7) 0.0122(6) 0.0017(6) C12 0.0333(8) 0.0322(9) 0.0437(9) 0.0021(7) 0.0176(7) -0.0030(6) C13 0.0423(9) 0.0369(10) 0.0548(10) 0.0047(8) 0.0181(8) 0.0015(7) C14 0.0531(10) 0.0333(9) 0.0683(12) -0.0026(9) 0.0277(9) 0.0024(8) C15 0.0593(11) 0.0369(10) 0.0592(11) -0.0115(8) 0.0322(9) -0.0080(8) C16 0.0442(9) 0.0416(10) 0.0463(9) -0.0029(8) 0.0189(7) -0.0071(7) C17 0.0330(8) 0.0326(9) 0.0435(9) 0.0004(7) 0.0177(7) -0.0048(6) C18 0.0310(8) 0.0370(9) 0.0397(9) -0.0009(7) 0.0082(6) -0.0028(6) C19 0.0255(8) 0.0432(10) 0.0449(9) -0.0002(7) 0.0087(6) -0.0001(6) C20 0.0445(10) 0.0478(11) 0.0658(12) 0.0124(9) 0.0234(9) 0.0120(8) C21 0.0500(11) 0.0679(14) 0.0798(14) 0.0106(11) 0.0320(10) 0.0227(10) C22 0.0413(11) 0.0795(16) 0.0806(15) 0.0038(12) 0.0332(10) 0.0019(10) C23 0.0600(13) 0.0635(14) 0.1030(18) -0.0027(12) 0.0480(13) -0.0155(10) C24 0.0551(12) 0.0448(11) 0.0919(16) -0.0068(10) 0.0407(11) -0.0098(9) C25 0.0383(9) 0.0398(10) 0.0439(10) 0.0018(8) 0.0150(7) -0.0029(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 N1 C25 1.143(2) . ? O1 C1 1.2248(19) . ? O2 C8 1.3575(18) . ? O2 C7 1.3778(19) . ? C1 C2 1.465(2) . ? C1 C9 1.470(2) . ? C2 C7 1.381(2) . ? C2 C3 1.402(2) . ? C3 C4 1.369(2) . ? C3 H3 0.9300 . ? C4 C5 1.386(3) . ? C4 H4 0.9300 . ? C5 C6 1.372(3) . ? C5 H5 0.9300 . ? C6 C7 1.385(2) . ? C6 H6 0.9300 . ? C8 C9 1.352(2) . ? C8 C18 1.501(2) . ? C9 C10 1.445(2) . ? C10 C11 1.349(2) . ? C10 H10 0.9300 . ? C11 C25 1.445(2) . ? C11 C12 1.474(2) . ? C12 C13 1.395(2) . ? C12 C17 1.403(2) . ? C13 C14 1.374(2) . ? C13 H13 0.9300 . ? C14 C15 1.373(2) . ? C14 H14 0.9300 . ? C15 C16 1.383(2) . ? C15 H15 0.9300 . ? C16 C17 1.384(2) . ? C16 H16 0.9300 . ? C17 C18 1.510(2) . ? C18 C19 1.529(2) . ? C18 H18 0.9800 . ? C19 C20 1.375(2) . ? C19 C24 1.383(2) . ? C20 C21 1.381(2) . ? C20 H20 0.9300 . ? C21 C22 1.370(3) . ? C21 H21 0.9300 . ? C22 C23 1.365(3) . ? C22 H22 0.9300 . ? C23 C24 1.382(3) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? 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 C8 O2 C7 119.17(12) . . ? O1 C1 C2 123.06(15) . . ? O1 C1 C9 122.26(14) . . ? C2 C1 C9 114.68(13) . . ? C7 C2 C3 117.87(15) . . ? C7 C2 C1 120.13(14) . . ? C3 C2 C1 121.98(15) . . ? C4 C3 C2 120.41(16) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.27(16) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 120.65(17) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 118.57(17) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? O2 C7 C2 121.46(14) . . ? O2 C7 C6 116.33(14) . . ? C2 C7 C6 122.21(15) . . ? C9 C8 O2 123.65(14) . . ? C9 C8 C18 125.34(14) . . ? O2 C8 C18 111.00(12) . . ? C8 C9 C10 122.64(14) . . ? C8 C9 C1 119.56(14) . . ? C10 C9 C1 117.75(13) . . ? C11 C10 C9 127.66(14) . . ? C11 C10 H10 116.2 . . ? C9 C10 H10 116.2 . . ? C10 C11 C25 116.49(14) . . ? C10 C11 C12 127.88(14) . . ? C25 C11 C12 115.20(14) . . ? C13 C12 C17 118.42(15) . . ? C13 C12 C11 119.24(14) . . ? C17 C12 C11 122.27(14) . . ? C14 C13 C12 121.39(17) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C15 C14 C13 119.99(16) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 119.62(16) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C17 121.31(16) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C16 C17 C12 119.13(15) . . ? C16 C17 C18 119.38(14) . . ? C12 C17 C18 121.45(14) . . ? C8 C18 C17 109.65(13) . . ? C8 C18 C19 113.36(13) . . ? C17 C18 C19 114.40(13) . . ? C8 C18 H18 106.3 . . ? C17 C18 H18 106.3 . . ? C19 C18 H18 106.3 . . ? C20 C19 C24 117.56(16) . . ? C20 C19 C18 121.32(15) . . ? C24 C19 C18 121.01(15) . . ? C19 C20 C21 121.08(17) . . ? C19 C20 H20 119.5 . . ? C21 C20 H20 119.5 . . ? C22 C21 C20 120.77(18) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C23 C22 C21 118.76(18) . . ? C23 C22 H22 120.6 . . ? C21 C22 H22 120.6 . . ? C22 C23 C24 120.63(19) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C23 C24 C19 121.11(17) . . ? C23 C24 H24 119.4 . . ? C19 C24 H24 119.4 . . ? N1 C25 C11 178.10(18) . . ? 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 O1 C1 C2 C7 -173.97(15) . . . . ? C9 C1 C2 C7 6.7(2) . . . . ? O1 C1 C2 C3 7.8(2) . . . . ? C9 C1 C2 C3 -171.58(13) . . . . ? C7 C2 C3 C4 -1.3(2) . . . . ? C1 C2 C3 C4 177.02(14) . . . . ? C2 C3 C4 C5 0.8(2) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C4 C5 C6 C7 -0.7(3) . . . . ? C8 O2 C7 C2 -8.8(2) . . . . ? C8 O2 C7 C6 172.20(13) . . . . ? C3 C2 C7 O2 -178.10(13) . . . . ? C1 C2 C7 O2 3.5(2) . . . . ? C3 C2 C7 C6 0.8(2) . . . . ? C1 C2 C7 C6 -177.53(14) . . . . ? C5 C6 C7 O2 179.12(15) . . . . ? C5 C6 C7 C2 0.1(3) . . . . ? C7 O2 C8 C9 3.0(2) . . . . ? C7 O2 C8 C18 -178.15(12) . . . . ? O2 C8 C9 C10 -174.74(13) . . . . ? C18 C8 C9 C10 6.6(2) . . . . ? O2 C8 C9 C1 7.8(2) . . . . ? C18 C8 C9 C1 -170.87(13) . . . . ? O1 C1 C9 C8 168.47(15) . . . . ? C2 C1 C9 C8 -12.2(2) . . . . ? O1 C1 C9 C10 -9.1(2) . . . . ? C2 C1 C9 C10 170.25(12) . . . . ? C8 C9 C10 C11 28.8(2) . . . . ? C1 C9 C10 C11 -153.73(15) . . . . ? C9 C10 C11 C25 176.30(14) . . . . ? C9 C10 C11 C12 4.2(2) . . . . ? C10 C11 C12 C13 144.94(15) . . . . ? C25 C11 C12 C13 -27.24(19) . . . . ? C10 C11 C12 C17 -31.9(2) . . . . ? C25 C11 C12 C17 155.87(14) . . . . ? C17 C12 C13 C14 3.2(2) . . . . ? C11 C12 C13 C14 -173.78(14) . . . . ? C12 C13 C14 C15 -0.1(2) . . . . ? C13 C14 C15 C16 -1.7(2) . . . . ? C14 C15 C16 C17 0.4(2) . . . . ? C15 C16 C17 C12 2.7(2) . . . . ? C15 C16 C17 C18 -175.06(14) . . . . ? C13 C12 C17 C16 -4.4(2) . . . . ? C11 C12 C17 C16 172.48(13) . . . . ? C13 C12 C17 C18 173.29(13) . . . . ? C11 C12 C17 C18 -9.8(2) . . . . ? C9 C8 C18 C17 -64.3(2) . . . . ? O2 C8 C18 C17 116.85(14) . . . . ? C9 C8 C18 C19 64.9(2) . . . . ? O2 C8 C18 C19 -113.95(14) . . . . ? C16 C17 C18 C8 -116.87(15) . . . . ? C12 C17 C18 C8 65.41(18) . . . . ? C16 C17 C18 C19 114.49(16) . . . . ? C12 C17 C18 C19 -63.23(18) . . . . ? C8 C18 C19 C20 31.3(2) . . . . ? C17 C18 C19 C20 158.07(15) . . . . ? C8 C18 C19 C24 -152.58(17) . . . . ? C17 C18 C19 C24 -25.8(2) . . . . ? C24 C19 C20 C21 -2.6(3) . . . . ? C18 C19 C20 C21 173.61(16) . . . . ? C19 C20 C21 C22 0.8(3) . . . . ? C20 C21 C22 C23 2.1(3) . . . . ? C21 C22 C23 C24 -3.1(4) . . . . ? C22 C23 C24 C19 1.3(3) . . . . ? C20 C19 C24 C23 1.6(3) . . . . ? C18 C19 C24 C23 -174.61(18) . . . . ? C10 C11 C25 N1 -179(100) . . . . ? C12 C11 C25 N1 -6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.241 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.048 data_cd201431 _database_code_depnum_ccdc_archive 'CCDC 792937' #TrackingRef '- cd201431.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H19 N O2' _chemical_formula_weight 341.39 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)/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 12.568(2) _cell_length_b 15.248(2) _cell_length_c 9.6494(15) _cell_angle_alpha 90.00 _cell_angle_beta 98.182(3) _cell_angle_gamma 90.00 _cell_volume 1830.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1257 _cell_measurement_theta_min 5.033 _cell_measurement_theta_max 47.799 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.305 _exptl_crystal_size_mid 0.237 _exptl_crystal_size_min 0.221 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.45053 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _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 '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 9251 _diffrn_reflns_av_R_equivalents 0.1108 _diffrn_reflns_av_sigmaI/netI 0.1071 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3392 _reflns_number_gt 1614 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0571P)^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_number_reflns 3392 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1162 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1479 _refine_ls_wR_factor_gt 0.1309 _refine_ls_goodness_of_fit_ref 0.840 _refine_ls_restrained_S_all 0.840 _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 0.3302(2) 0.52158(19) 0.3912(3) 0.0892(10) Uani 1 1 d . . . O1 O -0.02211(16) 0.44779(11) 0.6753(2) 0.0709(7) Uani 1 1 d . . . O2 O 0.06288(14) 0.19057(10) 0.6918(2) 0.0553(5) Uani 1 1 d . . . C1 C 0.0041(2) 0.36906(16) 0.6832(3) 0.0514(7) Uani 1 1 d . . . C2 C -0.0530(2) 0.30498(15) 0.7556(3) 0.0464(7) Uani 1 1 d . . . C3 C -0.1389(2) 0.32777(18) 0.8249(3) 0.0606(8) Uani 1 1 d . . . H3 H -0.1608 0.3860 0.8260 0.073 Uiso 1 1 calc R . . C4 C -0.1915(2) 0.26549(18) 0.8914(4) 0.0669(9) Uani 1 1 d . . . H4 H -0.2476 0.2816 0.9394 0.080 Uiso 1 1 calc R . . C5 C -0.1609(2) 0.17785(18) 0.8871(3) 0.0625(8) Uani 1 1 d . . . H5 H -0.1976 0.1355 0.9310 0.075 Uiso 1 1 calc R . . C6 C -0.0772(2) 0.15342(17) 0.8188(3) 0.0562(8) Uani 1 1 d . . . H6 H -0.0572 0.0949 0.8146 0.067 Uiso 1 1 calc R . . C7 C -0.0235(2) 0.21775(16) 0.7565(3) 0.0487(7) Uani 1 1 d . . . C8 C 0.1184(2) 0.24936(16) 0.6257(3) 0.0520(7) Uani 1 1 d . . . C9 C 0.0943(2) 0.33613(16) 0.6197(3) 0.0487(7) Uani 1 1 d . . . C10 C 0.1535(2) 0.39672(16) 0.5431(3) 0.0543(8) Uani 1 1 d . . . H10 H 0.1139 0.4423 0.4971 0.065 Uiso 1 1 calc R . . C11 C 0.2587(2) 0.39489(16) 0.5306(3) 0.0522(7) Uani 1 1 d . . . C12 C 0.3391(2) 0.33374(16) 0.6027(3) 0.0526(7) Uani 1 1 d . . . C13 C 0.3126(2) 0.24737(16) 0.6315(3) 0.0555(8) Uani 1 1 d . . . C14 C 0.2064(2) 0.20879(17) 0.5555(4) 0.0658(9) Uani 1 1 d . . . H14 H 0.1977 0.2332 0.4606 0.079 Uiso 1 1 calc R . . C15 C 0.4414(2) 0.36521(19) 0.6527(3) 0.0642(9) Uani 1 1 d . . . H15 H 0.4606 0.4215 0.6284 0.077 Uiso 1 1 calc R . . C16 C 0.5135(3) 0.3155(2) 0.7360(4) 0.0764(10) Uani 1 1 d . . . H16 H 0.5818 0.3373 0.7670 0.092 Uiso 1 1 calc R . . C17 C 0.4855(3) 0.2325(2) 0.7750(4) 0.0778(10) Uani 1 1 d . . . H17 H 0.5326 0.1998 0.8377 0.093 Uiso 1 1 calc R . . C18 C 0.3859(3) 0.19853(18) 0.7192(4) 0.0680(9) Uani 1 1 d . . . H18 H 0.3683 0.1415 0.7417 0.082 Uiso 1 1 calc R . . C19 C 0.2982(2) 0.46576(19) 0.4525(4) 0.0634(8) Uani 1 1 d . . . C20 C 0.2005(3) 0.11219(19) 0.5377(4) 0.0737(9) Uani 1 1 d . . . H20A H 0.1283 0.0964 0.4957 0.088 Uiso 1 1 calc R . . H20B H 0.2139 0.0848 0.6293 0.088 Uiso 1 1 calc R . . C21 C 0.2804(3) 0.07611(19) 0.4471(4) 0.0716(9) Uani 1 1 d . . . H21A H 0.2585 0.0935 0.3505 0.086 Uiso 1 1 calc R . . H21B H 0.3509 0.1009 0.4778 0.086 Uiso 1 1 calc R . . C22 C 0.2869(3) -0.0222(2) 0.4557(4) 0.0893(11) Uani 1 1 d . . . H22A H 0.3066 -0.0390 0.5529 0.107 Uiso 1 1 calc R . . H22B H 0.2162 -0.0463 0.4238 0.107 Uiso 1 1 calc R . . C23 C 0.3650(3) -0.0617(2) 0.3721(5) 0.1041(13) Uani 1 1 d . . . H23A H 0.3427 -0.0499 0.2746 0.156 Uiso 1 1 calc R . . H23B H 0.3681 -0.1239 0.3872 0.156 Uiso 1 1 calc R . . H23C H 0.4349 -0.0367 0.4005 0.156 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 N1 0.077(2) 0.0742(18) 0.121(3) 0.0223(18) 0.0309(18) -0.0121(16) O1 0.0663(14) 0.0365(11) 0.1148(19) 0.0083(10) 0.0296(12) 0.0108(9) O2 0.0423(11) 0.0334(9) 0.0917(15) -0.0031(9) 0.0145(10) 0.0009(8) C1 0.0429(17) 0.0410(16) 0.069(2) -0.0010(13) 0.0056(14) -0.0002(13) C2 0.0369(15) 0.0363(14) 0.0646(19) -0.0004(13) 0.0024(14) 0.0033(12) C3 0.0531(19) 0.0457(16) 0.085(2) 0.0040(15) 0.0172(17) 0.0087(14) C4 0.0520(19) 0.064(2) 0.087(2) 0.0061(17) 0.0187(17) 0.0062(16) C5 0.0492(19) 0.0543(18) 0.084(2) 0.0148(16) 0.0081(17) -0.0056(15) C6 0.0415(17) 0.0400(15) 0.085(2) 0.0081(15) 0.0015(16) -0.0018(14) C7 0.0330(15) 0.0405(15) 0.070(2) -0.0018(14) -0.0009(14) 0.0004(12) C8 0.0376(16) 0.0404(15) 0.078(2) -0.0059(14) 0.0096(15) -0.0052(13) C9 0.0360(15) 0.0391(14) 0.070(2) -0.0049(13) 0.0034(14) 0.0003(12) C10 0.0521(19) 0.0410(15) 0.070(2) -0.0021(14) 0.0087(15) -0.0025(14) C11 0.0489(18) 0.0408(14) 0.069(2) -0.0058(14) 0.0161(15) -0.0051(14) C12 0.0439(17) 0.0459(16) 0.071(2) -0.0069(14) 0.0188(15) -0.0042(14) C13 0.0422(17) 0.0429(15) 0.084(2) -0.0054(14) 0.0194(16) 0.0038(13) C14 0.0450(18) 0.0450(16) 0.109(3) -0.0028(16) 0.0170(18) -0.0017(14) C15 0.0464(18) 0.0580(18) 0.089(2) -0.0009(17) 0.0123(17) -0.0088(15) C16 0.052(2) 0.067(2) 0.108(3) -0.003(2) 0.002(2) -0.0043(17) C17 0.067(2) 0.075(2) 0.089(3) 0.0054(19) 0.003(2) 0.0164(19) C18 0.059(2) 0.0496(17) 0.098(3) 0.0023(17) 0.0222(19) 0.0023(16) C19 0.0520(19) 0.0562(18) 0.085(2) -0.0032(17) 0.0191(17) -0.0024(16) C20 0.063(2) 0.0600(18) 0.098(3) -0.0102(17) 0.0108(19) 0.0028(16) C21 0.063(2) 0.080(2) 0.074(2) -0.0219(17) 0.0190(17) 0.0080(17) C22 0.103(3) 0.066(2) 0.103(3) 0.001(2) 0.029(2) -0.001(2) C23 0.103(3) 0.072(2) 0.145(4) -0.001(2) 0.043(3) 0.022(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 C19 1.142(3) . ? O1 C1 1.244(3) . ? O2 C8 1.351(3) . ? O2 C7 1.390(3) . ? C1 C2 1.449(3) . ? C1 C9 1.453(4) . ? C2 C7 1.380(3) . ? C2 C3 1.393(4) . ? C3 C4 1.367(4) . ? C3 H3 0.9300 . ? C4 C5 1.393(4) . ? C4 H4 0.9300 . ? C5 C6 1.369(4) . ? C5 H5 0.9300 . ? C6 C7 1.376(3) . ? C6 H6 0.9300 . ? C8 C9 1.357(3) . ? C8 C14 1.509(4) . ? C9 C10 1.453(4) . ? C10 C11 1.345(4) . ? C10 H10 0.9300 . ? C11 C19 1.444(4) . ? C11 C12 1.474(4) . ? C12 C15 1.393(4) . ? C12 C13 1.396(3) . ? C13 C18 1.377(4) . ? C13 C14 1.546(4) . ? C14 C20 1.483(4) . ? C14 H14 0.9800 . ? C15 C16 1.355(4) . ? C15 H15 0.9300 . ? C16 C17 1.379(4) . ? C16 H16 0.9300 . ? C17 C18 1.391(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C20 C21 1.526(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.503(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.484(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? 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 C8 O2 C7 120.20(19) . . ? O1 C1 C2 122.4(3) . . ? O1 C1 C9 121.5(3) . . ? C2 C1 C9 116.1(2) . . ? C7 C2 C3 117.6(3) . . ? C7 C2 C1 120.1(3) . . ? C3 C2 C1 122.3(2) . . ? C4 C3 C2 120.7(3) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.6(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 118.3(3) . . ? C5 C6 H6 120.9 . . ? C7 C6 H6 120.9 . . ? C6 C7 C2 122.8(3) . . ? C6 C7 O2 116.5(2) . . ? C2 C7 O2 120.7(2) . . ? O2 C8 C9 122.7(3) . . ? O2 C8 C14 113.6(2) . . ? C9 C8 C14 123.6(3) . . ? C8 C9 C10 121.0(3) . . ? C8 C9 C1 120.1(3) . . ? C10 C9 C1 118.8(2) . . ? C11 C10 C9 127.9(3) . . ? C11 C10 H10 116.1 . . ? C9 C10 H10 116.1 . . ? C10 C11 C19 116.5(2) . . ? C10 C11 C12 125.9(3) . . ? C19 C11 C12 117.2(2) . . ? C15 C12 C13 119.4(3) . . ? C15 C12 C11 118.8(2) . . ? C13 C12 C11 121.6(2) . . ? C18 C13 C12 118.4(3) . . ? C18 C13 C14 122.9(3) . . ? C12 C13 C14 118.6(3) . . ? C20 C14 C8 115.5(3) . . ? C20 C14 C13 117.3(2) . . ? C8 C14 C13 105.6(2) . . ? C20 C14 H14 105.8 . . ? C8 C14 H14 105.8 . . ? C13 C14 H14 105.8 . . ? C16 C15 C12 121.3(3) . . ? C16 C15 H15 119.4 . . ? C12 C15 H15 119.4 . . ? C15 C16 C17 120.0(3) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C18 119.1(3) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C13 C18 C17 121.5(3) . . ? C13 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? N1 C19 C11 179.4(3) . . ? C14 C20 C21 113.4(3) . . ? C14 C20 H20A 108.9 . . ? C21 C20 H20A 108.9 . . ? C14 C20 H20B 108.9 . . ? C21 C20 H20B 108.9 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C20 111.3(3) . . ? C22 C21 H21A 109.4 . . ? C20 C21 H21A 109.4 . . ? C22 C21 H21B 109.4 . . ? C20 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? C23 C22 C21 114.1(3) . . ? C23 C22 H22A 108.7 . . ? C21 C22 H22A 108.7 . . ? C23 C22 H22B 108.7 . . ? C21 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 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 O1 C1 C2 C7 177.4(2) . . . . ? C9 C1 C2 C7 -2.6(4) . . . . ? O1 C1 C2 C3 -2.0(4) . . . . ? C9 C1 C2 C3 178.0(3) . . . . ? C7 C2 C3 C4 0.1(4) . . . . ? C1 C2 C3 C4 179.5(3) . . . . ? C2 C3 C4 C5 -1.7(5) . . . . ? C3 C4 C5 C6 1.1(4) . . . . ? C4 C5 C6 C7 0.9(4) . . . . ? C5 C6 C7 C2 -2.5(4) . . . . ? C5 C6 C7 O2 178.2(2) . . . . ? C3 C2 C7 C6 2.0(4) . . . . ? C1 C2 C7 C6 -177.4(2) . . . . ? C3 C2 C7 O2 -178.7(2) . . . . ? C1 C2 C7 O2 1.9(4) . . . . ? C8 O2 C7 C6 178.6(2) . . . . ? C8 O2 C7 C2 -0.8(4) . . . . ? C7 O2 C8 C9 0.6(4) . . . . ? C7 O2 C8 C14 -177.4(2) . . . . ? O2 C8 C9 C10 -177.7(2) . . . . ? C14 C8 C9 C10 0.0(4) . . . . ? O2 C8 C9 C1 -1.5(4) . . . . ? C14 C8 C9 C1 176.3(3) . . . . ? O1 C1 C9 C8 -177.6(2) . . . . ? C2 C1 C9 C8 2.5(4) . . . . ? O1 C1 C9 C10 -1.3(4) . . . . ? C2 C1 C9 C10 178.8(2) . . . . ? C8 C9 C10 C11 -35.9(4) . . . . ? C1 C9 C10 C11 147.8(3) . . . . ? C9 C10 C11 C19 -177.5(3) . . . . ? C9 C10 C11 C12 -5.2(5) . . . . ? C10 C11 C12 C15 -140.8(3) . . . . ? C19 C11 C12 C15 31.4(4) . . . . ? C10 C11 C12 C13 34.1(4) . . . . ? C19 C11 C12 C13 -153.7(3) . . . . ? C15 C12 C13 C18 5.6(4) . . . . ? C11 C12 C13 C18 -169.2(3) . . . . ? C15 C12 C13 C14 -170.0(3) . . . . ? C11 C12 C13 C14 15.1(4) . . . . ? O2 C8 C14 C20 15.2(4) . . . . ? C9 C8 C14 C20 -162.8(3) . . . . ? O2 C8 C14 C13 -116.2(3) . . . . ? C9 C8 C14 C13 65.9(4) . . . . ? C18 C13 C14 C20 -21.0(5) . . . . ? C12 C13 C14 C20 154.4(3) . . . . ? C18 C13 C14 C8 109.3(3) . . . . ? C12 C13 C14 C8 -75.2(3) . . . . ? C13 C12 C15 C16 -4.1(5) . . . . ? C11 C12 C15 C16 170.9(3) . . . . ? C12 C15 C16 C17 -1.2(5) . . . . ? C15 C16 C17 C18 4.8(5) . . . . ? C12 C13 C18 C17 -2.0(5) . . . . ? C14 C13 C18 C17 173.4(3) . . . . ? C16 C17 C18 C13 -3.2(5) . . . . ? C10 C11 C19 N1 169(100) . . . . ? C12 C11 C19 N1 -4(35) . . . . ? C8 C14 C20 C21 171.2(3) . . . . ? C13 C14 C20 C21 -63.2(4) . . . . ? C14 C20 C21 C22 168.7(3) . . . . ? C20 C21 C22 C23 -178.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C6 H6 O1 0.93 2.45 3.372(3) 171.1 2_546 C10 H10 O1 0.93 2.52 3.435(3) 167.1 3_566 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.482 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.040