Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Jing Wang' _publ_contact_author_address ; School of Pharmaceutical Sciences Hebei Medical University Shijiazhuang Hebei 050017 CHINA ; _publ_contact_author_email JINGWANG@HOME.IPE.AC.CN _publ_section_title ; Three concomitant polymorphs of 1:1 4,4'-dihydroxybenzophenone/1,2-bis(4-pyridyl)-ethylene: applications of hydrothermal method in searching polymorphs ; loop_ _publ_author_name 'Jing Wang.' 'Liyu Ding.' 'Caiqin Yan.' data_p2c _database_code_depnum_ccdc_archive 'CCDC 633775' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H20 N2 O3' _chemical_formula_weight 396.43 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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 18.9100(16) _cell_length_b 5.9777(6) _cell_length_c 17.2465(17) _cell_angle_alpha 90.00 _cell_angle_beta 96.236(4) _cell_angle_gamma 90.00 _cell_volume 1938.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(1) _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 'SMART CCD 1000' _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 17139 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 32.21 _reflns_number_total 5965 _reflns_number_gt 4270 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.0680P)^2^+0.4249P] 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 0.024(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5965 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 O1 O 0.25824(5) 0.68587(16) 0.36289(6) 0.0221(2) Uani 1 1 d . . . O2 O 0.5000 1.2719(2) 0.2500 0.0383(4) Uani 1 2 d S . . O3 O 0.23740(5) 0.28203(16) 0.13526(6) 0.0256(2) Uani 1 1 d . . . O4 O 0.00873(18) -0.3204(3) 0.27159(14) 0.0371(8) Uani 0.50 1 d P . . H2 H 0.2687(11) 0.165(4) 0.1245(12) 0.056(6) Uiso 1 1 d . . . C1 C 0.40292(6) 1.0713(2) 0.33378(8) 0.0186(2) Uani 1 1 d . . . C2 C 0.34336(6) 0.9846(2) 0.36271(7) 0.0189(3) Uani 1 1 d . . . H2A H 0.3179(8) 1.072(3) 0.3998(9) 0.024(4) Uiso 1 1 d . . . C3 C 0.31819(6) 0.7738(2) 0.33842(7) 0.0168(2) Uani 1 1 d . . . C4 C 0.35483(6) 0.6480(2) 0.28738(7) 0.0171(2) Uani 1 1 d . . . H4A H 0.3363(8) 0.505(3) 0.2699(9) 0.019(4) Uiso 1 1 d . . . C5 C 0.41590(6) 0.7348(2) 0.26029(7) 0.0160(2) Uani 1 1 d . . . H5A H 0.4402(7) 0.645(3) 0.2243(8) 0.018(4) Uiso 1 1 d . . . C6 C 0.44042(6) 0.9487(2) 0.28230(7) 0.0164(2) Uani 1 1 d . . . C7 C 0.5000 1.0662(3) 0.2500 0.0205(4) Uani 1 2 d S . . C8 C 0.05974(6) 0.2167(2) 0.19365(7) 0.0174(2) Uani 1 1 d . . . H8A H 0.0170(7) 0.306(2) 0.1902(8) 0.016(4) Uiso 1 1 d . . . C9 C 0.11896(7) 0.3098(2) 0.16501(8) 0.0192(3) Uani 1 1 d . . . H9A H 0.1173(8) 0.458(3) 0.1415(9) 0.019(4) Uiso 1 1 d . . . C10 C 0.18197(6) 0.1871(2) 0.16644(7) 0.0183(2) Uani 1 1 d . . . C11 C 0.18574(7) -0.0274(2) 0.19884(7) 0.0188(3) Uani 1 1 d . . . H11A H 0.2307(8) -0.115(3) 0.2017(9) 0.024(4) Uiso 1 1 d . . . C12 C 0.12636(7) -0.1186(2) 0.22673(8) 0.0206(3) Uani 1 1 d . . . H12A H 0.1289(8) -0.268(3) 0.2482(10) 0.031(4) Uiso 1 1 d . . . C13 C 0.06222(7) 0.0004(2) 0.22429(7) 0.0189(3) Uani 1 1 d . . . C14 C 0.0000 -0.1170(3) 0.2500 0.0353(5) Uani 1 2 d S . . C15 C 0.30037(7) 0.7584(2) 0.05883(8) 0.0212(3) Uani 1 1 d . . . H15A H 0.2503(8) 0.723(3) 0.0601(9) 0.024(4) Uiso 1 1 d . . . C16 C 0.34461(6) 0.6048(2) 0.02814(8) 0.0196(3) Uani 1 1 d . . . H16A H 0.3243(8) 0.461(3) 0.0083(9) 0.024(4) Uiso 1 1 d . . . C17 C 0.41678(6) 0.6554(2) 0.02740(7) 0.0168(2) Uani 1 1 d . . . C18 C 0.43994(6) 0.8626(2) 0.05773(7) 0.0187(3) Uani 1 1 d . . . H18A H 0.4905(8) 0.910(3) 0.0588(9) 0.028(4) Uiso 1 1 d . . . C19 C 0.39176(7) 1.0071(2) 0.08593(8) 0.0197(3) Uani 1 1 d . . . H19A H 0.4059(7) 1.151(3) 0.1074(8) 0.019(4) Uiso 1 1 d . . . C20 C 0.46435(6) 0.4944(2) -0.00471(7) 0.0181(2) Uani 1 1 d . . . H20A H 0.4413(8) 0.378(3) -0.0361(9) 0.026(4) Uiso 1 1 d . . . C21 C 0.16343(8) 1.2139(2) 0.38719(8) 0.0261(3) Uani 1 1 d . . . H21A H 0.1909(9) 1.250(3) 0.3449(10) 0.038(5) Uiso 1 1 d . . . C22 C 0.11423(9) 1.3644(3) 0.40920(11) 0.0410(4) Uani 1 1 d . . . H22A H 0.1085(10) 1.504(3) 0.3805(12) 0.049(6) Uiso 1 1 d . . . C23 C 0.07386(8) 1.3106(3) 0.46961(13) 0.0504(6) Uani 1 1 d . . . C24 C 0.08796(8) 1.1055(3) 0.50588(10) 0.0407(5) Uani 1 1 d . . . H24A H 0.0632(10) 1.061(3) 0.5476(12) 0.052(6) Uiso 1 1 d . . . C25 C 0.13791(7) 0.9628(3) 0.47992(8) 0.0239(3) Uani 1 1 d . . . H25A H 0.1490(9) 0.818(3) 0.5033(10) 0.032(4) Uiso 1 1 d . . . C26' C 0.02207(12) 1.5039(4) 0.47167(14) 0.0134(4) Uani 0.50 1 d P . . H26A H 0.0084(9) 1.635(3) 0.4331(11) 0.042(5) Uiso 1 1 d . . . C26 C 0.01659(14) 1.4110(4) 0.51588(16) 0.0199(5) Uani 0.50 1 d P . . N1 N 0.32251(6) 0.95824(19) 0.08693(6) 0.0204(2) Uani 1 1 d . . . N2 N 0.17545(5) 1.01353(18) 0.42074(6) 0.0184(2) Uani 1 1 d . . . H1A H 0.4196(8) 1.217(3) 0.3499(9) 0.024(4) Uiso 1 1 d . . . H1 H 0.2335(11) 0.804(4) 0.3861(12) 0.059(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0192(4) 0.0192(5) 0.0301(5) 0.0029(4) 0.0125(4) 0.0024(3) O2 0.0324(8) 0.0127(7) 0.0737(12) 0.000 0.0231(8) 0.000 O3 0.0194(5) 0.0212(5) 0.0388(6) 0.0032(4) 0.0155(4) 0.0001(4) O4 0.0328(17) 0.0157(8) 0.067(2) 0.0093(9) 0.0261(18) 0.0036(9) C1 0.0172(5) 0.0155(6) 0.0230(6) -0.0029(5) 0.0015(5) 0.0023(4) C2 0.0177(6) 0.0199(6) 0.0197(6) -0.0033(5) 0.0042(5) 0.0045(5) C3 0.0156(5) 0.0173(6) 0.0181(6) 0.0041(4) 0.0041(4) 0.0032(4) C4 0.0180(6) 0.0132(5) 0.0207(6) 0.0006(4) 0.0053(4) 0.0018(4) C5 0.0169(5) 0.0141(5) 0.0176(6) 0.0006(4) 0.0046(4) 0.0029(4) C6 0.0147(5) 0.0142(5) 0.0206(6) 0.0008(4) 0.0032(4) 0.0024(4) C7 0.0184(8) 0.0135(8) 0.0303(10) 0.000 0.0056(7) 0.000 C8 0.0173(6) 0.0181(6) 0.0176(6) 0.0006(4) 0.0051(4) 0.0023(4) C9 0.0204(6) 0.0169(6) 0.0213(6) 0.0042(5) 0.0068(5) 0.0026(5) C10 0.0170(6) 0.0194(6) 0.0193(6) 0.0009(5) 0.0061(4) -0.0003(4) C11 0.0195(6) 0.0199(6) 0.0177(6) 0.0015(5) 0.0051(5) 0.0049(5) C12 0.0266(6) 0.0146(6) 0.0221(6) 0.0018(5) 0.0090(5) 0.0036(5) C13 0.0209(6) 0.0153(6) 0.0222(6) -0.0019(5) 0.0103(5) -0.0005(4) C14 0.0331(11) 0.0147(9) 0.0636(15) 0.000 0.0300(11) 0.000 C15 0.0146(6) 0.0242(6) 0.0253(7) 0.0044(5) 0.0038(5) 0.0007(5) C16 0.0164(6) 0.0196(6) 0.0230(6) 0.0026(5) 0.0029(5) -0.0009(5) C17 0.0155(5) 0.0198(6) 0.0152(5) 0.0037(4) 0.0028(4) 0.0009(4) C18 0.0154(5) 0.0229(6) 0.0182(6) 0.0020(5) 0.0042(4) -0.0022(5) C19 0.0202(6) 0.0200(6) 0.0196(6) 0.0020(5) 0.0050(5) -0.0012(5) C20 0.0168(6) 0.0191(6) 0.0187(6) 0.0010(5) 0.0032(4) 0.0000(4) C21 0.0319(7) 0.0215(7) 0.0241(7) -0.0013(5) -0.0014(6) 0.0016(5) C22 0.0367(9) 0.0233(7) 0.0573(11) -0.0163(7) -0.0217(8) 0.0131(6) C23 0.0141(6) 0.0542(11) 0.0803(14) -0.0539(11) -0.0064(7) 0.0082(7) C24 0.0190(7) 0.0656(12) 0.0405(9) -0.0356(9) 0.0162(6) -0.0153(7) C25 0.0206(6) 0.0316(7) 0.0202(6) -0.0054(5) 0.0061(5) -0.0070(5) C26' 0.0132(11) 0.0133(10) 0.0142(11) 0.0001(9) 0.0040(9) 0.0014(9) C26 0.0193(13) 0.0217(13) 0.0193(14) -0.0044(11) 0.0037(9) -0.0026(11) N1 0.0181(5) 0.0218(5) 0.0221(5) 0.0040(4) 0.0060(4) 0.0018(4) N2 0.0180(5) 0.0201(5) 0.0179(5) -0.0012(4) 0.0053(4) 0.0023(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 O1 C3 1.3576(14) . ? O2 C7 1.229(2) . ? O3 C10 1.3535(14) . ? O4 O4 0.781(5) 2 ? O4 C14 1.277(3) . ? C1 C2 1.3813(17) . ? C1 C6 1.4019(16) . ? C2 C3 1.3956(18) . ? C3 C4 1.3975(17) . ? C4 C5 1.3923(16) . ? C5 C6 1.3986(17) . ? C6 C7 1.4864(14) . ? C7 C6 1.4864(14) 2_655 ? C8 C9 1.3885(17) . ? C8 C13 1.3957(17) . ? C9 C10 1.3969(17) . ? C10 C11 1.3977(17) . ? C11 C12 1.3809(17) . ? C12 C13 1.4026(17) . ? C13 C14 1.4787(15) . ? C14 O4 1.277(3) 2 ? C14 C13 1.4787(15) 2 ? C15 N1 1.3393(17) . ? C15 C16 1.3854(18) . ? C16 C17 1.3992(16) . ? C17 C18 1.3965(18) . ? C17 C20 1.4662(17) . ? C18 C19 1.3817(18) . ? C19 N1 1.3437(16) . ? C20 C20 1.342(2) 3_665 ? C21 N2 1.3389(17) . ? C21 C22 1.377(2) . ? C22 C23 1.394(3) . ? C23 C24 1.389(3) . ? C23 C26' 1.518(3) . ? C23 C26 1.536(3) . ? C24 C25 1.383(2) . ? C25 N2 1.3397(16) . ? C26' C26 0.935(3) 3_586 ? C26' C26 0.958(3) . ? C26' C26' 1.353(4) 3_586 ? C26 C26' 0.935(3) 3_586 ? C26 C26 1.324(6) 3_586 ? 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 O4 O4 C14 72.19(11) 2 . ? C2 C1 C6 121.39(12) . . ? C1 C2 C3 119.70(11) . . ? O1 C3 C2 121.69(11) . . ? O1 C3 C4 118.39(11) . . ? C2 C3 C4 119.91(11) . . ? C5 C4 C3 119.80(11) . . ? C4 C5 C6 120.82(11) . . ? C5 C6 C1 118.32(11) . . ? C5 C6 C7 124.94(11) . . ? C1 C6 C7 116.52(11) . . ? O2 C7 C6 118.20(7) . 2_655 ? O2 C7 C6 118.20(7) . . ? C6 C7 C6 123.59(15) 2_655 . ? C9 C8 C13 120.71(11) . . ? C8 C9 C10 120.19(12) . . ? O3 C10 C9 117.97(11) . . ? O3 C10 C11 122.36(11) . . ? C9 C10 C11 119.67(11) . . ? C12 C11 C10 119.56(11) . . ? C11 C12 C13 121.51(12) . . ? C8 C13 C12 118.32(11) . . ? C8 C13 C14 123.92(12) . . ? C12 C13 C14 117.65(12) . . ? O4 C14 O4 35.6(2) 2 . ? O4 C14 C13 116.50(17) 2 . ? O4 C14 C13 117.22(17) . . ? O4 C14 C13 117.22(17) 2 2 ? O4 C14 C13 116.50(17) . 2 ? C13 C14 C13 123.35(17) . 2 ? N1 C15 C16 123.47(11) . . ? C15 C16 C17 119.36(12) . . ? C18 C17 C16 117.05(11) . . ? C18 C17 C20 122.90(11) . . ? C16 C17 C20 120.05(11) . . ? C19 C18 C17 119.64(11) . . ? N1 C19 C18 123.33(12) . . ? C20 C20 C17 124.83(15) 3_665 . ? N2 C21 C22 123.60(15) . . ? C21 C22 C23 119.76(17) . . ? C24 C23 C22 116.51(13) . . ? C24 C23 C26' 138.96(19) . . ? C22 C23 C26' 104.41(19) . . ? C24 C23 C26 102.86(19) . . ? C22 C23 C26 140.6(2) . . ? C26' C23 C26 36.57(13) . . ? C25 C24 C23 120.19(15) . . ? N2 C25 C24 122.99(15) . . ? C26 C26' C26 88.7(3) 3_586 . ? C26 C26' C26' 45.1(2) 3_586 3_586 ? C26 C26' C26' 43.7(2) . 3_586 ? C26 C26' C23 160.5(3) 3_586 . ? C26 C26' C23 72.7(3) . . ? C26' C26' C23 116.2(3) 3_586 . ? C26' C26 C26' 91.3(3) 3_586 . ? C26' C26 C26 46.4(2) 3_586 3_586 ? C26' C26 C26 44.9(2) . 3_586 ? C26' C26 C23 161.0(3) 3_586 . ? C26' C26 C23 70.7(3) . . ? C26 C26 C23 115.4(3) 3_586 . ? C15 N1 C19 117.13(11) . . ? C21 N2 C25 116.90(12) . . ? 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 O1 H1 N2 0.96(2) 1.81(2) 2.7608(13) 171.6(19) . O3 H2 N1 0.95(2) 1.77(2) 2.7060(14) 169.9(19) 1_545 _diffrn_measured_fraction_theta_max 0.871 _diffrn_reflns_theta_full 32.21 _diffrn_measured_fraction_theta_full 0.871 _refine_diff_density_max 0.486 _refine_diff_density_min -0.512 _refine_diff_density_rms 0.098 # Attachment '2.CIF' data_pca21 _database_code_depnum_ccdc_archive 'CCDC 633776' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H20 N2 O3' _chemical_formula_weight 396.43 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 Pca2(1) 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 43.6174(15) _cell_length_b 5.9652(2) _cell_length_c 7.4612(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1941.30(12) _cell_formula_units_Z 4 _cell_measurement_temperature 90(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate-like _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(1) _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 'SMART CCD 1000' _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 19126 _diffrn_reflns_av_R_equivalents 0.1024 _diffrn_reflns_av_sigmaI/netI 0.1163 _diffrn_reflns_limit_h_min -62 _diffrn_reflns_limit_h_max 54 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 0.93 _diffrn_reflns_theta_max 30.49 _reflns_number_total 4775 _reflns_number_gt 2984 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.0431P)^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 SHELXL _refine_ls_extinction_coef 0.0156(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 4775 _refine_ls_number_parameters 352 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1055 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.954 _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 O1 O -0.21868(4) 0.2626(3) 0.9495(3) 0.0261(5) Uani 1 1 d . . . O2 O -0.09976(4) 0.8153(3) 0.8190(3) 0.0288(5) Uani 1 1 d . . . O3 O 0.01579(4) 0.1920(3) 0.9023(3) 0.0221(5) Uani 1 1 d . . . N1 N 0.23857(5) 1.4111(4) 0.9540(3) 0.0198(5) Uani 1 1 d . . . N2 N 0.06158(5) 0.5075(3) 0.8714(3) 0.0186(5) Uani 1 1 d . . . C1 C -0.13739(6) 0.2898(4) 0.8458(4) 0.0173(6) Uani 1 1 d . . . C2 C -0.16701(6) 0.2106(5) 0.8651(4) 0.0184(6) Uani 1 1 d . . . C3 C -0.18968(6) 0.3468(4) 0.9383(4) 0.0194(7) Uani 1 1 d . . . C4 C -0.18209(6) 0.5605(5) 0.9960(4) 0.0198(6) Uani 1 1 d . . . C5 C -0.15247(6) 0.6416(5) 0.9720(4) 0.0184(6) Uani 1 1 d . . . C6 C -0.12954(6) 0.5074(4) 0.8965(4) 0.0170(6) Uani 1 1 d . . . C7 C -0.09943(6) 0.6156(4) 0.8603(4) 0.0186(6) Uani 1 1 d . . . C8 C -0.06999(6) 0.4935(4) 0.8685(4) 0.0166(6) Uani 1 1 d . . . C9 C -0.06633(6) 0.2814(4) 0.9479(4) 0.0172(6) Uani 1 1 d . . . C10 C -0.03740(6) 0.1813(4) 0.9576(4) 0.0181(6) Uani 1 1 d . . . C11 C -0.01203(6) 0.2917(4) 0.8893(4) 0.0182(6) Uani 1 1 d . . . C12 C -0.01551(6) 0.5028(5) 0.8089(4) 0.0176(6) Uani 1 1 d . . . C13 C -0.04383(6) 0.6007(5) 0.8015(4) 0.0179(6) Uani 1 1 d . . . C14 C 0.21060(6) 1.4584(5) 1.0194(4) 0.0203(7) Uani 1 1 d . . . C15 C 0.18567(7) 1.3151(5) 1.0046(4) 0.0218(7) Uani 1 1 d . . . C16 C 0.18879(6) 1.1133(4) 0.9119(4) 0.0193(6) Uani 1 1 d . . . C17 C 0.21798(6) 1.0662(5) 0.8448(4) 0.0213(7) Uani 1 1 d . . . C18 C 0.24181(7) 1.2135(5) 0.8682(4) 0.0220(7) Uani 1 1 d . . . C19 C 0.16375(7) 0.9542(5) 0.8783(4) 0.0215(6) Uani 1 1 d . . . C20 C 0.13550(6) 0.9721(5) 0.9445(4) 0.0210(6) Uani 1 1 d . . . C21 C 0.11048(6) 0.8098(5) 0.9142(4) 0.0183(7) Uani 1 1 d . . . C22 C 0.08102(6) 0.8657(5) 0.9658(4) 0.0205(6) Uani 1 1 d . . . C23 C 0.05759(6) 0.7112(5) 0.9434(4) 0.0196(6) Uani 1 1 d . . . C24 C 0.09043(6) 0.4550(5) 0.8194(4) 0.0202(6) Uani 1 1 d . . . C25 C 0.11505(6) 0.5990(5) 0.8383(4) 0.0204(7) Uani 1 1 d . . . H23A H 0.0357(6) 0.743(4) 0.975(4) 0.014(7) Uiso 1 1 d . . . H10A H -0.0364(6) 0.030(4) 1.022(4) 0.016(7) Uiso 1 1 d . . . H19A H 0.1693(5) 0.815(4) 0.800(4) 0.016(7) Uiso 1 1 d . . . H5A H -0.1486(6) 0.795(5) 1.003(4) 0.031(9) Uiso 1 1 d . . . H20A H 0.1306(6) 1.112(4) 1.024(4) 0.020(8) Uiso 1 1 d . . . H1A H -0.1229(5) 0.180(4) 0.788(3) 0.005(6) Uiso 1 1 d . . . H2 H 0.0307(8) 0.292(6) 0.867(6) 0.068(13) Uiso 1 1 d . . . H2A H -0.1739(7) 0.072(5) 0.830(5) 0.036(9) Uiso 1 1 d . . . H9A H -0.0848(6) 0.205(5) 1.017(4) 0.029(8) Uiso 1 1 d . . . H12A H 0.0019(6) 0.574(4) 0.753(3) 0.010(7) Uiso 1 1 d . . . H17A H 0.2231(6) 0.924(5) 0.777(4) 0.028(9) Uiso 1 1 d . . . H22A H 0.0757(6) 1.014(5) 1.020(4) 0.027(8) Uiso 1 1 d . . . H13A H -0.0466(7) 0.752(5) 0.751(4) 0.030(9) Uiso 1 1 d . . . H14A H 0.2106(6) 1.605(5) 1.082(4) 0.025(9) Uiso 1 1 d . . . H18A H 0.2613(7) 1.180(5) 0.832(5) 0.036(9) Uiso 1 1 d . . . H25A H 0.1366(6) 0.548(5) 0.796(4) 0.033(9) Uiso 1 1 d . . . H24A H 0.0930(6) 0.307(5) 0.763(4) 0.029(9) Uiso 1 1 d . . . H15A H 0.1689(7) 1.370(5) 1.052(4) 0.025(9) Uiso 1 1 d . . . H1 H -0.2336(8) 0.405(6) 0.941(6) 0.078(13) Uiso 1 1 d . . . H4A H -0.1976(6) 0.655(5) 1.055(4) 0.024(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0160(10) 0.0215(10) 0.0408(13) 0.0030(11) 0.0019(10) -0.0004(8) O2 0.0248(11) 0.0154(11) 0.0462(14) 0.0033(10) 0.0029(11) 0.0021(8) O3 0.0139(11) 0.0189(10) 0.0336(14) 0.0001(10) -0.0033(9) 0.0008(8) N1 0.0172(12) 0.0220(12) 0.0202(13) -0.0011(12) 0.0036(11) -0.0001(10) N2 0.0170(12) 0.0195(13) 0.0193(14) 0.0024(11) 0.0000(11) 0.0004(10) C1 0.0194(15) 0.0156(14) 0.0170(15) 0.0015(13) 0.0007(13) 0.0032(12) C2 0.0164(14) 0.0175(15) 0.0213(16) 0.0013(13) -0.0022(13) 0.0022(12) C3 0.0156(14) 0.0220(15) 0.0204(16) 0.0090(13) 0.0000(13) 0.0006(12) C4 0.0204(15) 0.0182(15) 0.0209(17) 0.0006(13) -0.0003(13) 0.0065(12) C5 0.0194(15) 0.0131(13) 0.0226(16) -0.0042(13) -0.0055(13) 0.0036(12) C6 0.0185(14) 0.0156(14) 0.0168(16) -0.0002(12) -0.0018(11) 0.0034(11) C7 0.0212(15) 0.0150(14) 0.0197(17) -0.0024(13) -0.0007(13) 0.0007(12) C8 0.0172(14) 0.0165(14) 0.0161(15) -0.0036(13) 0.0015(12) 0.0010(11) C9 0.0191(14) 0.0167(14) 0.0160(14) -0.0029(13) 0.0007(13) -0.0016(11) C10 0.0184(14) 0.0178(14) 0.0181(15) 0.0021(13) -0.0014(13) 0.0015(11) C11 0.0167(15) 0.0212(14) 0.0166(16) -0.0057(13) -0.0011(12) 0.0031(12) C12 0.0146(14) 0.0192(15) 0.0191(16) 0.0015(13) -0.0006(12) -0.0011(12) C13 0.0190(15) 0.0179(15) 0.0167(15) 0.0002(12) -0.0010(12) -0.0027(12) C14 0.0188(16) 0.0231(16) 0.0192(16) 0.0003(13) -0.0013(12) 0.0012(13) C15 0.0130(15) 0.0287(17) 0.0237(17) 0.0034(14) 0.0042(13) 0.0028(13) C16 0.0191(14) 0.0215(15) 0.0172(16) 0.0053(12) -0.0044(12) -0.0027(12) C17 0.0199(15) 0.0216(15) 0.0223(17) 0.0016(14) 0.0042(13) 0.0008(12) C18 0.0163(15) 0.0261(16) 0.0235(18) 0.0022(14) 0.0028(14) 0.0024(13) C19 0.0230(15) 0.0215(15) 0.0200(16) 0.0028(14) 0.0002(13) 0.0000(12) C20 0.0220(16) 0.0226(15) 0.0185(15) 0.0023(14) -0.0019(13) -0.0013(12) C21 0.0158(14) 0.0230(15) 0.0163(17) 0.0020(13) 0.0000(12) -0.0032(11) C22 0.0187(14) 0.0203(14) 0.0227(16) 0.0044(14) 0.0012(13) 0.0004(12) C23 0.0147(14) 0.0240(15) 0.0203(16) -0.0009(14) 0.0038(13) 0.0017(12) C24 0.0206(15) 0.0219(15) 0.0181(16) 0.0041(13) -0.0010(12) 0.0025(13) C25 0.0105(14) 0.0311(16) 0.0196(17) 0.0047(14) -0.0003(12) 0.0002(12) _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 C3 1.363(3) . ? O2 C7 1.230(3) . ? O3 C11 1.355(3) . ? N1 C14 1.344(3) . ? N1 C18 1.348(4) . ? N2 C23 1.340(3) . ? N2 C24 1.354(3) . ? C1 C2 1.383(4) . ? C1 C6 1.394(4) . ? C2 C3 1.392(4) . ? C3 C4 1.385(4) . ? C4 C5 1.391(4) . ? C5 C6 1.399(4) . ? C6 C7 1.488(4) . ? C7 C8 1.477(4) . ? C8 C13 1.400(4) . ? C8 C9 1.406(4) . ? C9 C10 1.398(4) . ? C10 C11 1.385(4) . ? C11 C12 1.403(4) . ? C12 C13 1.367(4) . ? C14 C15 1.388(4) . ? C15 C16 1.395(4) . ? C16 C17 1.396(4) . ? C16 C19 1.468(4) . ? C17 C18 1.373(4) . ? C19 C20 1.332(4) . ? C20 C21 1.476(4) . ? C21 C22 1.382(4) . ? C21 C25 1.393(4) . ? C22 C23 1.386(4) . ? C24 C25 1.382(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 N1 C18 116.8(2) . . ? C23 N2 C24 116.5(2) . . ? C2 C1 C6 121.3(3) . . ? C1 C2 C3 120.3(3) . . ? O1 C3 C4 122.8(3) . . ? O1 C3 C2 117.9(2) . . ? C4 C3 C2 119.3(3) . . ? C3 C4 C5 120.1(3) . . ? C4 C5 C6 121.1(3) . . ? C1 C6 C5 117.8(2) . . ? C1 C6 C7 124.8(2) . . ? C5 C6 C7 117.1(2) . . ? O2 C7 C8 119.8(2) . . ? O2 C7 C6 117.1(2) . . ? C8 C7 C6 123.1(2) . . ? C13 C8 C9 118.0(2) . . ? C13 C8 C7 117.9(2) . . ? C9 C8 C7 124.0(2) . . ? C10 C9 C8 120.6(3) . . ? C11 C10 C9 120.0(3) . . ? O3 C11 C10 118.7(2) . . ? O3 C11 C12 121.4(2) . . ? C10 C11 C12 119.8(2) . . ? C13 C12 C11 119.9(3) . . ? C12 C13 C8 121.8(3) . . ? N1 C14 C15 123.6(3) . . ? C14 C15 C16 119.6(3) . . ? C15 C16 C17 116.1(3) . . ? C15 C16 C19 124.7(3) . . ? C17 C16 C19 119.1(3) . . ? C18 C17 C16 121.1(3) . . ? N1 C18 C17 122.7(3) . . ? C20 C19 C16 125.0(3) . . ? C19 C20 C21 125.1(3) . . ? C22 C21 C25 117.6(3) . . ? C22 C21 C20 119.1(3) . . ? C25 C21 C20 123.3(2) . . ? C21 C22 C23 119.4(3) . . ? N2 C23 C22 123.7(2) . . ? N2 C24 C25 123.3(3) . . ? C24 C25 C21 119.4(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 O3 H2 N2 0.92(4) 1.86(3) 2.754(3) 162(4) . O1 H1 N1 1.07(4) 1.64(4) 2.696(3) 168(3) 3_475 _diffrn_measured_fraction_theta_max 0.832 _diffrn_reflns_theta_full 30.49 _diffrn_measured_fraction_theta_full 0.832 _refine_diff_density_max 0.387 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.099 # Attachment '3.CIF' data_c2c _database_code_depnum_ccdc_archive 'CCDC 633777' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H20 N2 O3' _chemical_formula_weight 396.43 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.760(2) _cell_length_b 6.0368(5) _cell_length_c 13.6085(12) _cell_angle_alpha 90.00 _cell_angle_beta 101.123(3) _cell_angle_gamma 90.00 _cell_volume 1915.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(1) _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 'SMART CCD 1000' _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 6628 _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 32.34 _reflns_number_total 3074 _reflns_number_gt 2536 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.0609P)^2^+0.8534P] 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 0.0171(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3074 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1177 _refine_ls_wR_factor_gt 0.1078 _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 N1 N 0.16434(4) -0.25068(15) 0.74787(6) 0.01645(19) Uani 1 1 d . . . O1 O 0.11904(3) 0.07490(13) 0.60992(5) 0.01824(18) Uani 1 1 d . . . O2 O 0.0000 -0.50730(18) 0.2500 0.0216(2) Uani 1 2 d S . . C1 C 0.05218(4) 0.02577(16) 0.34599(7) 0.01398(19) Uani 1 1 d . . . C2 C 0.08279(4) 0.11070(17) 0.43586(7) 0.0151(2) Uani 1 1 d . . . C3 C 0.08902(4) -0.01368(17) 0.52390(7) 0.01414(19) Uani 1 1 d . . . C4 C 0.06470(4) -0.22452(18) 0.52128(7) 0.0170(2) Uani 1 1 d . . . C5 C 0.03557(4) -0.30980(17) 0.43154(7) 0.0161(2) Uani 1 1 d . . . C6 C 0.02845(4) -0.18685(16) 0.34260(7) 0.01245(18) Uani 1 1 d . . . C7 C 0.0000 -0.3030(2) 0.2500 0.0134(2) Uani 1 2 d S . . C8 C 0.14486(4) -0.45177(18) 0.76752(7) 0.0179(2) Uani 1 1 d . . . C9 C 0.17313(4) -0.59130(17) 0.84223(7) 0.0158(2) Uani 1 1 d . . . C10 C 0.22551(4) -0.52340(16) 0.90032(7) 0.01281(18) Uani 1 1 d . . . C11 C 0.24628(4) -0.31585(16) 0.87893(7) 0.01394(19) Uani 1 1 d . . . C12 C 0.21441(4) -0.18615(17) 0.80400(7) 0.01478(19) Uani 1 1 d . . . C13 C 0.25934(4) -0.65861(16) 0.98032(7) 0.01404(19) Uani 1 1 d . . . H13A H 0.2983(6) -0.603(2) 1.0066(10) 0.015(3) Uiso 1 1 d . . . H4A H 0.0673(7) -0.309(3) 0.5833(12) 0.030(4) Uiso 1 1 d . . . H2A H 0.1012(6) 0.255(2) 0.4385(10) 0.018(3) Uiso 1 1 d . . . H1A H 0.0497(6) 0.112(2) 0.2863(10) 0.018(3) Uiso 1 1 d . . . H9A H 0.1547(6) -0.736(2) 0.8518(10) 0.017(3) Uiso 1 1 d . . . H12A H 0.2275(6) -0.039(2) 0.7889(10) 0.021(3) Uiso 1 1 d . . . H5A H 0.0190(6) -0.459(2) 0.4282(11) 0.024(4) Uiso 1 1 d . . . H8A H 0.1083(6) -0.497(2) 0.7266(11) 0.020(3) Uiso 1 1 d . . . H11A H 0.2838(6) -0.264(2) 0.9145(10) 0.018(3) Uiso 1 1 d . . . H1 H 0.1295(8) -0.049(3) 0.6551(14) 0.053(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0177(4) 0.0181(4) 0.0131(4) 0.0022(3) 0.0019(3) 0.0028(3) O1 0.0202(4) 0.0187(4) 0.0128(3) 0.0002(3) -0.0045(2) -0.0016(3) O2 0.0301(6) 0.0126(5) 0.0193(5) 0.000 -0.0026(4) 0.000 C1 0.0152(4) 0.0136(5) 0.0124(4) 0.0020(3) 0.0006(3) 0.0003(3) C2 0.0162(4) 0.0129(5) 0.0146(4) 0.0013(3) -0.0012(3) -0.0009(3) C3 0.0125(4) 0.0169(5) 0.0120(4) -0.0006(3) -0.0003(3) 0.0003(3) C4 0.0185(4) 0.0186(5) 0.0127(4) 0.0039(3) 0.0002(3) -0.0032(3) C5 0.0182(4) 0.0153(5) 0.0140(4) 0.0027(3) 0.0008(3) -0.0036(3) C6 0.0123(4) 0.0134(4) 0.0113(4) 0.0009(3) 0.0015(3) 0.0005(3) C7 0.0139(5) 0.0131(6) 0.0129(5) 0.000 0.0016(4) 0.000 C8 0.0153(4) 0.0207(5) 0.0162(4) 0.0031(4) -0.0008(3) 0.0006(3) C9 0.0153(4) 0.0161(5) 0.0153(4) 0.0019(3) 0.0011(3) -0.0004(3) C10 0.0140(4) 0.0150(5) 0.0097(3) 0.0007(3) 0.0028(3) 0.0015(3) C11 0.0158(4) 0.0152(5) 0.0106(4) 0.0000(3) 0.0021(3) -0.0002(3) C12 0.0192(4) 0.0147(5) 0.0109(4) 0.0013(3) 0.0040(3) 0.0010(3) C13 0.0144(4) 0.0154(5) 0.0119(4) 0.0008(3) 0.0014(3) 0.0008(3) _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 C12 1.3416(13) . ? N1 C8 1.3443(14) . ? O1 C3 1.3576(11) . ? O2 C7 1.2331(18) . ? C1 C2 1.3943(13) . ? C1 C6 1.3991(14) . ? C2 C3 1.3974(13) . ? C3 C4 1.3954(14) . ? C4 C5 1.3817(13) . ? C5 C6 1.4019(13) . ? C6 C7 1.4861(11) . ? C7 C6 1.4861(11) 2 ? C8 C9 1.3896(13) . ? C9 C10 1.4008(13) . ? C10 C11 1.3977(14) . ? C10 C13 1.4697(13) . ? C11 C12 1.3887(13) . ? C13 C13 1.3390(19) 7_537 ? 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 C12 N1 C8 116.77(8) . . ? C2 C1 C6 120.33(9) . . ? C1 C2 C3 120.36(9) . . ? O1 C3 C4 121.83(8) . . ? O1 C3 C2 118.61(9) . . ? C4 C3 C2 119.56(8) . . ? C5 C4 C3 119.79(9) . . ? C4 C5 C6 121.48(9) . . ? C1 C6 C5 118.46(8) . . ? C1 C6 C7 125.13(8) . . ? C5 C6 C7 116.21(9) . . ? O2 C7 C6 118.16(6) . . ? O2 C7 C6 118.16(6) . 2 ? C6 C7 C6 123.67(12) . 2 ? N1 C8 C9 123.81(9) . . ? C8 C9 C10 119.15(9) . . ? C11 C10 C9 117.11(9) . . ? C11 C10 C13 119.17(8) . . ? C9 C10 C13 123.71(9) . . ? C12 C11 C10 119.60(9) . . ? N1 C12 C11 123.54(9) . . ? C13 C13 C10 125.29(11) 7_537 . ? 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 O1 H1 N1 0.97(2) 1.83(2) 2.7868(11) 167.4(17) . _diffrn_measured_fraction_theta_max 0.899 _diffrn_reflns_theta_full 32.34 _diffrn_measured_fraction_theta_full 0.899 _refine_diff_density_max 0.550 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.098