# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Alessia Bacchi' 'Giulia Cantoni' 'Mauro Carcelli' 'Tiziana Chiodo' 'Cecilia De Filippo' 'Silvio Pipolo' _publ_contact_author_name 'Alessia Bacchi' _publ_contact_author_email ALESSIA.BACCHI@UNIPR.IT _publ_section_title ; A discussion on the solid state organization of 4-pyridil imino compounds and on the cocrystallization between their molecular precursors ; # Attachment 'bacchi.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 712725' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Hg Hg -4.2923 7.6849 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p21/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 10.8998(5) _cell_length_b 11.4338(4) _cell_length_c 17.9406(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.393(5) _cell_angle_gamma 90.00 _cell_volume 2233.92(14) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6 _cell_measurement_theta_max 16 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.654 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens AED diffractometer' _diffrn_measurement_method '\q/2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4453 _diffrn_reflns_av_R_equivalents 0.0126 _diffrn_reflns_av_sigmaI/netI 0.0082 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.06 _diffrn_reflns_theta_max 70.03 _reflns_number_total 4234 _reflns_number_gt 3638 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+0.4061P] 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 0.0067(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4234 _refine_ls_number_parameters 294 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1213 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.14242(14) -0.31795(13) 0.62988(8) 0.0709(4) Uani 1 1 d . . . N2 N 0.28338(12) -0.61091(11) 0.44627(6) 0.0585(3) Uani 1 1 d . . . N3 N -0.42195(13) -0.75679(13) 1.10931(7) 0.0694(4) Uani 1 1 d . . . N4 N -0.18913(12) -0.47398(12) 0.95695(7) 0.0624(3) Uani 1 1 d . . . O1 O 0.43788(12) -0.88148(9) 0.20920(6) 0.0684(3) Uani 1 1 d . . . H1O H 0.4839 -0.8443 0.1831 0.103 Uiso 1 1 calc R . . O2 O 0.02763(13) -0.20022(10) 0.74162(6) 0.0740(4) Uani 1 1 d . . . H2O H 0.0667 -0.2403 0.7130 0.111 Uiso 1 1 calc R . . C1 C 0.07912(18) -0.30235(17) 0.56570(10) 0.0770(5) Uani 1 1 d . . . H1A H 0.0177 -0.2459 0.5639 0.092 Uiso 1 1 calc R . . C2 C 0.09924(16) -0.36495(16) 0.50182(9) 0.0705(4) Uani 1 1 d . . . H2A H 0.0527 -0.3499 0.4583 0.085 Uiso 1 1 calc R . . C3 C 0.18910(13) -0.45023(13) 0.50288(8) 0.0533(3) Uani 1 1 d . . . C4 C 0.25609(16) -0.46533(15) 0.56906(8) 0.0644(4) Uani 1 1 d . . . H4 H 0.3187 -0.5206 0.5724 0.077 Uiso 1 1 calc R . . C5 C 0.23020(17) -0.39853(17) 0.63016(9) 0.0712(5) Uani 1 1 d . . . H5 H 0.2767 -0.4104 0.6741 0.085 Uiso 1 1 calc R . . C6 C 0.21447(13) -0.52269(13) 0.43577(8) 0.0539(3) Uani 1 1 d . . . C7 C 0.15490(19) -0.48772(18) 0.36244(9) 0.0817(6) Uani 1 1 d . . . H7A H 0.1689 -0.5472 0.3260 0.123 Uiso 1 1 calc R . . H7B H 0.1894 -0.4151 0.3464 0.123 Uiso 1 1 calc R . . H7C H 0.0682 -0.4784 0.3679 0.123 Uiso 1 1 calc R . . C8 C 0.31995(13) -0.67835(13) 0.38403(7) 0.0528(3) Uani 1 1 d . . . C9 C 0.40221(15) -0.63325(14) 0.33513(8) 0.0621(4) Uani 1 1 d . . . H9 H 0.4305 -0.5570 0.3415 0.074 Uiso 1 1 calc R . . C10 C 0.44317(15) -0.69953(14) 0.27685(8) 0.0593(4) Uani 1 1 d . . . H10 H 0.4991 -0.6680 0.2447 0.071 Uiso 1 1 calc R . . C11 C 0.40135(13) -0.81247(13) 0.26619(7) 0.0528(3) Uani 1 1 d . . . C12 C 0.32032(15) -0.85826(14) 0.31566(8) 0.0604(4) Uani 1 1 d . . . H12 H 0.2920 -0.9345 0.3093 0.073 Uiso 1 1 calc R . . C13 C 0.28080(14) -0.79239(14) 0.37444(8) 0.0593(4) Uani 1 1 d . . . H13 H 0.2275 -0.8250 0.4078 0.071 Uiso 1 1 calc R . . C14 C -0.31960(17) -0.69461(17) 1.11983(9) 0.0701(4) Uani 1 1 d . . . H14 H -0.2779 -0.6997 1.1660 0.084 Uiso 1 1 calc R . . C15 C -0.27166(15) -0.62354(15) 1.06681(8) 0.0656(4) Uani 1 1 d . . . H15 H -0.1993 -0.5825 1.0774 0.079 Uiso 1 1 calc R . . C16 C -0.33117(13) -0.61301(13) 0.99750(8) 0.0553(3) Uani 1 1 d . . . C17 C -0.43613(16) -0.67816(18) 0.98591(10) 0.0776(5) Uani 1 1 d . . . H17 H -0.4792 -0.6752 0.9401 0.093 Uiso 1 1 calc R . . C18 C -0.47754(18) -0.74777(19) 1.04218(10) 0.0838(6) Uani 1 1 d . . . H18 H -0.5487 -0.7911 1.0327 0.101 Uiso 1 1 calc R . . C19 C -0.28061(14) -0.53763(13) 0.93812(8) 0.0562(4) Uani 1 1 d . . . C20 C -0.3397(2) -0.5443(2) 0.86119(10) 0.0920(7) Uani 1 1 d . . . H20A H -0.2967 -0.4940 0.8283 0.138 Uiso 1 1 calc R . . H20B H -0.4238 -0.5199 0.8627 0.138 Uiso 1 1 calc R . . H20C H -0.3363 -0.6234 0.8434 0.138 Uiso 1 1 calc R . . C21 C -0.13364(13) -0.40455(14) 0.90146(8) 0.0552(4) Uani 1 1 d . . . C22 C -0.04894(15) -0.45334(14) 0.85558(8) 0.0620(4) Uani 1 1 d . . . H22 H -0.0287 -0.5320 0.8609 0.074 Uiso 1 1 calc R . . C23 C 0.00620(14) -0.38709(13) 0.80189(8) 0.0583(4) Uani 1 1 d . . . H23 H 0.0637 -0.4211 0.7717 0.070 Uiso 1 1 calc R . . C24 C -0.02397(14) -0.27072(13) 0.79314(7) 0.0541(3) Uani 1 1 d . . . C25 C -0.10774(15) -0.22143(14) 0.83941(9) 0.0632(4) Uani 1 1 d . . . H25 H -0.1283 -0.1429 0.8340 0.076 Uiso 1 1 calc R . . C26 C -0.16129(15) -0.28728(15) 0.89365(9) 0.0639(4) Uani 1 1 d . . . H26 H -0.2163 -0.2525 0.9251 0.077 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 0.0845(9) 0.0709(9) 0.0590(8) -0.0119(7) 0.0219(7) -0.0104(8) N2 0.0684(8) 0.0604(7) 0.0469(6) 0.0008(5) 0.0068(5) 0.0087(6) N3 0.0773(9) 0.0752(9) 0.0571(8) -0.0026(6) 0.0197(6) -0.0138(7) N4 0.0664(7) 0.0710(8) 0.0501(7) -0.0005(6) 0.0046(5) -0.0169(7) O1 0.0890(8) 0.0592(6) 0.0585(6) -0.0082(5) 0.0218(5) -0.0018(6) O2 0.1066(10) 0.0590(6) 0.0583(6) -0.0026(5) 0.0265(6) -0.0133(6) C1 0.0795(11) 0.0769(11) 0.0756(11) -0.0162(9) 0.0137(9) 0.0110(9) C2 0.0747(10) 0.0756(11) 0.0609(9) -0.0101(8) -0.0001(8) 0.0120(9) C3 0.0583(8) 0.0539(8) 0.0482(7) -0.0013(6) 0.0073(6) -0.0045(6) C4 0.0740(10) 0.0674(9) 0.0519(8) -0.0019(7) 0.0034(7) 0.0039(8) C5 0.0864(12) 0.0780(11) 0.0495(8) -0.0053(8) 0.0058(8) -0.0061(10) C6 0.0594(8) 0.0552(8) 0.0471(7) -0.0013(6) 0.0029(6) 0.0004(7) C7 0.1034(14) 0.0847(12) 0.0555(9) -0.0107(9) -0.0144(9) 0.0309(11) C8 0.0585(8) 0.0562(8) 0.0440(7) 0.0028(6) 0.0040(6) 0.0074(6) C9 0.0781(10) 0.0499(8) 0.0591(8) -0.0020(7) 0.0136(7) -0.0043(7) C10 0.0680(9) 0.0578(8) 0.0534(8) 0.0032(7) 0.0162(7) -0.0043(7) C11 0.0602(8) 0.0528(8) 0.0455(7) 0.0009(6) 0.0039(6) 0.0045(6) C12 0.0705(9) 0.0537(8) 0.0576(8) -0.0006(7) 0.0089(7) -0.0082(7) C13 0.0625(8) 0.0638(9) 0.0524(8) 0.0045(7) 0.0122(6) -0.0044(7) C14 0.0789(11) 0.0826(11) 0.0491(8) 0.0004(8) 0.0059(7) -0.0113(9) C15 0.0670(9) 0.0768(10) 0.0529(8) -0.0003(7) 0.0020(7) -0.0171(8) C16 0.0558(8) 0.0587(8) 0.0517(8) -0.0023(6) 0.0057(6) -0.0051(6) C17 0.0722(11) 0.0983(13) 0.0616(9) 0.0105(9) -0.0056(8) -0.0283(10) C18 0.0749(11) 0.1060(15) 0.0706(11) 0.0077(10) 0.0049(9) -0.0355(11) C19 0.0571(8) 0.0593(8) 0.0522(8) 0.0018(6) 0.0007(6) -0.0064(7) C20 0.0952(13) 0.1124(16) 0.0664(11) 0.0258(11) -0.0208(9) -0.0430(12) C21 0.0572(8) 0.0623(9) 0.0461(7) -0.0029(6) 0.0014(6) -0.0134(7) C22 0.0752(10) 0.0520(8) 0.0593(8) -0.0004(7) 0.0078(7) -0.0017(7) C23 0.0658(9) 0.0599(9) 0.0497(7) -0.0064(6) 0.0094(6) -0.0003(7) C24 0.0643(8) 0.0551(8) 0.0431(7) -0.0048(6) 0.0034(6) -0.0116(7) C25 0.0750(10) 0.0524(8) 0.0630(9) -0.0042(7) 0.0112(7) -0.0016(7) C26 0.0643(9) 0.0670(10) 0.0614(9) -0.0077(7) 0.0147(7) -0.0034(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 N1 C5 1.328(2) . ? N1 C1 1.329(2) . ? N2 C6 1.2671(19) . ? N2 C8 1.4274(18) . ? N3 C18 1.329(2) . ? N3 C14 1.330(2) . ? N4 C19 1.2688(19) . ? N4 C21 1.4273(18) . ? O1 C11 1.3639(17) . ? O2 C24 1.3652(17) . ? C1 C2 1.377(2) . ? C2 C3 1.382(2) . ? C3 C4 1.379(2) . ? C3 C6 1.4966(19) . ? C4 C5 1.375(2) . ? C6 C7 1.497(2) . ? C8 C9 1.380(2) . ? C8 C13 1.380(2) . ? C9 C10 1.381(2) . ? C10 C11 1.380(2) . ? C11 C12 1.381(2) . ? C12 C13 1.379(2) . ? C14 C15 1.371(2) . ? C15 C16 1.383(2) . ? C16 C17 1.374(2) . ? C16 C19 1.494(2) . ? C17 C18 1.376(2) . ? C19 C20 1.500(2) . ? C21 C22 1.380(2) . ? C21 C26 1.380(2) . ? C22 C23 1.382(2) . ? C23 C24 1.378(2) . ? C24 C25 1.380(2) . ? C25 C26 1.379(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 116.36(14) . . ? C6 N2 C8 119.79(12) . . ? C18 N3 C14 115.79(14) . . ? C19 N4 C21 118.98(12) . . ? N1 C1 C2 123.81(17) . . ? C1 C2 C3 119.54(16) . . ? C4 C3 C2 116.74(14) . . ? C4 C3 C6 120.97(14) . . ? C2 C3 C6 122.29(13) . . ? C5 C4 C3 119.88(16) . . ? N1 C5 C4 123.66(16) . . ? N2 C6 C3 116.70(12) . . ? N2 C6 C7 125.16(13) . . ? C3 C6 C7 118.12(13) . . ? C9 C8 C13 118.64(13) . . ? C9 C8 N2 120.36(14) . . ? C13 C8 N2 120.85(13) . . ? C8 C9 C10 121.03(14) . . ? C11 C10 C9 120.21(14) . . ? O1 C11 C10 122.69(13) . . ? O1 C11 C12 118.49(13) . . ? C10 C11 C12 118.82(13) . . ? C13 C12 C11 120.85(14) . . ? C12 C13 C8 120.41(13) . . ? N3 C14 C15 124.07(15) . . ? C14 C15 C16 119.81(15) . . ? C17 C16 C15 116.43(14) . . ? C17 C16 C19 122.33(14) . . ? C15 C16 C19 121.21(13) . . ? C16 C17 C18 119.94(16) . . ? N3 C18 C17 123.94(16) . . ? N4 C19 C16 116.77(13) . . ? N4 C19 C20 125.20(14) . . ? C16 C19 C20 118.03(13) . . ? C22 C21 C26 118.74(14) . . ? C22 C21 N4 120.31(14) . . ? C26 C21 N4 120.93(14) . . ? C21 C22 C23 121.02(15) . . ? C24 C23 C22 119.99(14) . . ? O2 C24 C23 122.97(13) . . ? O2 C24 C25 117.89(14) . . ? C23 C24 C25 119.12(14) . . ? C26 C25 C24 120.78(15) . . ? C25 C26 C21 120.33(14) . . ? 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 H1O N3 0.82 1.98 2.7942(17) 172.4 1_654 O2 H2O N1 0.82 1.95 2.7578(17) 168.8 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 70.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.158 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.031 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 712726' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 N2 O' _chemical_formula_weight 198.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M p21ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, y+1/2, -z' 'x+1/2, -y, -z' 'x+1/2, -y+1/2, z' _cell_length_a 7.7618(6) _cell_length_b 22.981(3) _cell_length_c 5.6539(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1008.51(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 6 _cell_measurement_theta_max 16 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.688 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens AED diffractometer' _diffrn_measurement_method '\q/2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 1918 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 69.99 _reflns_number_total 1037 _reflns_number_gt 726 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0540P)^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 1037 _refine_ls_number_parameters 137 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1097 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.957 _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 0.8929(5) 0.31897(9) 0.0766(4) 0.0902(8) Uani 1 1 d . . . H1O H 0.8785 0.2937 -0.0239 0.135 Uiso 1 1 calc R . . N1 N 0.8641(5) 0.73165(10) -0.7423(5) 0.0808(8) Uani 1 1 d . . . N2 N 0.8331(4) 0.53541(11) -0.3540(5) 0.0747(8) Uani 1 1 d . . . C1 C 0.9474(6) 0.73345(14) -0.5366(6) 0.0850(12) Uani 1 1 d . . . H1 H 0.9983 0.7684 -0.4922 0.102 Uiso 1 1 calc R . . C2 C 0.9629(5) 0.68663(13) -0.3852(6) 0.0806(11) Uani 1 1 d . . . H2 H 1.0257 0.6903 -0.2458 0.097 Uiso 1 1 calc R . . C3 C 0.8852(5) 0.63455(13) -0.4410(6) 0.0692(9) Uani 1 1 d . . . C4 C 0.7918(5) 0.63268(14) -0.6530(6) 0.0750(9) Uani 1 1 d . . . H4 H 0.7345 0.5989 -0.6979 0.090 Uiso 1 1 calc R . . C5 C 0.7862(5) 0.68130(13) -0.7933(7) 0.0802(10) Uani 1 1 d . . . H5 H 0.7239 0.6791 -0.9336 0.096 Uiso 1 1 calc R . . C6 C 0.9033(5) 0.58210(13) -0.2938(6) 0.0729(9) Uani 1 1 d . . . H6 H 0.9674 0.5837 -0.1550 0.087 Uiso 1 1 calc R . . C7 C 0.8504(5) 0.48256(13) -0.2286(6) 0.0662(8) Uani 1 1 d . . . C8 C 0.9314(5) 0.47478(14) -0.0091(6) 0.0768(10) Uani 1 1 d . . . H8 H 0.9776 0.5066 0.0703 0.092 Uiso 1 1 calc R . . C9 C 0.9427(5) 0.42015(14) 0.0884(6) 0.0766(10) Uani 1 1 d . . . H9 H 0.9972 0.4154 0.2336 0.092 Uiso 1 1 calc R . . C10 C 0.8749(5) 0.37231(13) -0.0246(6) 0.0703(9) Uani 1 1 d . . . C11 C 0.7914(5) 0.38011(14) -0.2393(6) 0.0787(10) Uani 1 1 d . . . H11 H 0.7435 0.3484 -0.3177 0.094 Uiso 1 1 calc R . . C12 C 0.7800(5) 0.43456(13) -0.3351(6) 0.0751(10) Uani 1 1 d . . . H12 H 0.7222 0.4392 -0.4779 0.090 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 O1 0.116(2) 0.0800(14) 0.0749(14) 0.0089(11) -0.0053(18) -0.0020(17) N1 0.094(2) 0.0691(15) 0.0798(18) -0.0062(15) 0.0137(19) 0.0014(17) N2 0.078(2) 0.0686(15) 0.0773(17) -0.0089(14) -0.0019(16) 0.0013(15) C1 0.103(3) 0.066(2) 0.086(2) -0.0158(18) 0.024(2) -0.014(2) C2 0.087(3) 0.081(2) 0.073(2) -0.0118(18) 0.011(2) -0.008(2) C3 0.071(2) 0.0678(18) 0.0688(18) -0.0080(15) 0.0135(19) 0.0021(18) C4 0.077(2) 0.0621(17) 0.086(2) -0.0090(18) 0.003(2) -0.0012(17) C5 0.086(3) 0.075(2) 0.080(2) -0.0069(17) 0.004(2) 0.002(2) C6 0.078(2) 0.0787(19) 0.0623(18) -0.0071(16) 0.0054(19) -0.001(2) C7 0.0685(19) 0.0652(16) 0.0650(18) -0.0077(15) -0.0004(17) 0.0016(15) C8 0.088(3) 0.077(2) 0.0655(19) -0.0157(16) -0.009(2) -0.001(2) C9 0.086(3) 0.086(2) 0.0584(17) -0.0043(17) -0.0093(19) 0.005(2) C10 0.075(3) 0.0730(19) 0.0626(18) -0.0005(16) 0.0049(19) 0.0029(19) C11 0.089(3) 0.0720(18) 0.075(2) -0.0073(17) -0.017(2) -0.007(2) C12 0.084(3) 0.0742(19) 0.0668(19) -0.0032(16) -0.0150(19) -0.0009(19) _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 C10 1.360(3) . ? N1 C1 1.331(5) . ? N1 C5 1.337(4) . ? N2 C6 1.251(4) . ? N2 C7 1.413(4) . ? C1 C2 1.380(5) . ? C2 C3 1.377(4) . ? C3 C4 1.402(5) . ? C3 C6 1.471(4) . ? C4 C5 1.371(4) . ? C7 C12 1.370(4) . ? C7 C8 1.403(5) . ? C8 C9 1.374(4) . ? C9 C10 1.376(4) . ? C10 C11 1.388(4) . ? C11 C12 1.366(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 C1 N1 C5 115.8(3) . . ? C6 N2 C7 124.0(3) . . ? N1 C1 C2 124.1(3) . . ? C3 C2 C1 119.8(3) . . ? C2 C3 C4 116.7(3) . . ? C2 C3 C6 122.7(3) . . ? C4 C3 C6 120.5(3) . . ? C5 C4 C3 119.1(3) . . ? N1 C5 C4 124.5(4) . . ? N2 C6 C3 120.5(3) . . ? C12 C7 C8 117.7(3) . . ? C12 C7 N2 115.7(3) . . ? C8 C7 N2 126.6(3) . . ? C9 C8 C7 120.0(3) . . ? C8 C9 C10 121.3(3) . . ? O1 C10 C9 119.0(3) . . ? O1 C10 C11 122.2(3) . . ? C9 C10 C11 118.8(3) . . ? C12 C11 C10 119.7(3) . . ? C11 C12 C7 122.5(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 69.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.095 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.033 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 712727' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 N2 O' _chemical_formula_weight 350.40 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 p21/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 6.452(5) _cell_length_b 18.073(13) _cell_length_c 16.549(11) _cell_angle_alpha 90.00 _cell_angle_beta 109.52(3) _cell_angle_gamma 90.00 _cell_volume 1819(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 800 _cell_measurement_theta_min 4 _cell_measurement_theta_max 18 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.763395 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS procedure' _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 'SMART diffractometer' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.2 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15389 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0135 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 23.29 _reflns_number_total 2623 _reflns_number_gt 2116 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0701P)^2^+1.3650P] 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 2623 _refine_ls_number_parameters 245 _refine_ls_number_restraints 70 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1648 _refine_ls_wR_factor_gt 0.1551 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.088 _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 2.2383(3) -0.77882(13) 1.02241(15) 0.0522(6) Uani 1 1 d U . . N2 N 1.4465(4) -0.77438(16) 0.83513(18) 0.0724(8) Uani 1 1 d U . . O1 O 0.5849(3) -0.80577(10) 0.60964(14) 0.0608(6) Uani 1 1 d U . . H1O H 0.5296 -0.7648 0.5960 0.091 Uiso 1 1 calc R . . C1 C 2.1860(5) -0.83741(17) 0.97134(19) 0.0604(8) Uani 1 1 d U . . H1 H 2.2968 -0.8713 0.9744 0.072 Uiso 1 1 calc R . . C2 C 1.9818(5) -0.85154(19) 0.91479(19) 0.0630(8) Uani 1 1 d U . . H2 H 1.9560 -0.8942 0.8814 0.076 Uiso 1 1 calc R . . C3 C 1.8166(5) -0.80307(18) 0.90754(18) 0.0601(8) Uani 1 1 d U . . C4 C 1.8619(4) -0.74154(19) 0.9606(2) 0.0665(9) Uani 1 1 d U . . H4 H 1.7521 -0.7075 0.9584 0.080 Uiso 1 1 calc R . . C5 C 2.0777(5) -0.73153(17) 1.0180(2) 0.0596(8) Uani 1 1 d U . . H5 H 2.1083 -0.6905 1.0539 0.072 Uiso 1 1 calc R . . C6 C 1.5920(5) -0.81740(19) 0.8426(2) 0.0668(8) Uani 1 1 d U . . H6 H 1.5672 -0.8596 0.8085 0.080 Uiso 1 1 calc R . . C7 C 1.2300(4) -0.78781(17) 0.77316(18) 0.0555(7) Uani 1 1 d U . . C8 C 1.1398(4) -0.85549(17) 0.74026(18) 0.0545(7) Uani 1 1 d U . . H8 H 1.2268 -0.8977 0.7551 0.065 Uiso 1 1 calc R . . C9 C 0.9215(4) -0.86248(14) 0.68532(16) 0.0455(6) Uani 1 1 d U . . C10 C 0.7944(4) -0.79796(14) 0.66433(16) 0.0446(6) Uani 1 1 d U . . C11 C 0.8835(4) -0.72907(15) 0.69548(16) 0.0463(6) Uani 1 1 d U . . C12 C 1.1000(4) -0.72581(16) 0.75044(18) 0.0543(7) Uani 1 1 d U . . H12 H 1.1588 -0.6802 0.7726 0.065 Uiso 1 1 calc R . . C13 C 0.7600(4) -0.65867(15) 0.66995(17) 0.0486(7) Uani 1 1 d U . . C14 C 0.5865(5) -0.63942(18) 0.6975(2) 0.0635(8) Uani 1 1 d U . . H14 H 0.5400 -0.6723 0.7312 0.076 Uiso 1 1 calc R . . C15 C 0.4822(6) -0.5723(2) 0.6755(2) 0.0775(10) Uani 1 1 d U . . H15 H 0.3663 -0.5599 0.6945 0.093 Uiso 1 1 calc R . . C16 C 0.5488(7) -0.5237(2) 0.6258(3) 0.0841(11) Uani 1 1 d U . . H16 H 0.4783 -0.4783 0.6110 0.101 Uiso 1 1 calc R . . C17 C 0.7190(7) -0.54193(19) 0.5978(3) 0.0850(11) Uani 1 1 d U . . H17 H 0.7634 -0.5090 0.5636 0.102 Uiso 1 1 calc R . . C18 C 0.8248(5) -0.60864(17) 0.6200(2) 0.0670(8) Uani 1 1 d U . . H18 H 0.9415 -0.6203 0.6012 0.080 Uiso 1 1 calc R . . C19 C 0.8368(4) -0.93571(15) 0.64994(18) 0.0489(7) Uani 1 1 d U . . C20 C 0.9666(5) -0.98180(18) 0.6204(3) 0.0759(10) Uani 1 1 d U . . H20 H 1.1051 -0.9657 0.6223 0.091 Uiso 1 1 calc R . . C21 C 0.8963(6) -1.0505(2) 0.5884(3) 0.0894(12) Uani 1 1 d U . . H21 H 0.9877 -1.0804 0.5693 0.107 Uiso 1 1 calc R . . C22 C 0.6930(6) -1.07595(18) 0.5842(2) 0.0710(9) Uani 1 1 d U . . H22 H 0.6455 -1.1227 0.5622 0.085 Uiso 1 1 calc R . . C23 C 0.5613(5) -1.03136(18) 0.6127(2) 0.0669(9) Uani 1 1 d U . . H23 H 0.4230 -1.0480 0.6104 0.080 Uiso 1 1 calc R . . C24 C 0.6307(4) -0.96219(16) 0.6450(2) 0.0589(8) Uani 1 1 d U . . H24 H 0.5382 -0.9326 0.6638 0.071 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 0.0344(12) 0.0570(14) 0.0548(14) 0.0005(11) 0.0010(10) -0.0025(10) N2 0.0478(14) 0.0828(19) 0.0811(19) 0.0231(15) 0.0141(13) 0.0042(14) O1 0.0337(10) 0.0494(11) 0.0769(14) -0.0029(10) -0.0112(9) 0.0029(8) C1 0.0466(16) 0.0663(19) 0.0636(19) -0.0046(16) 0.0124(14) -0.0035(14) C2 0.0485(17) 0.076(2) 0.0569(18) -0.0052(16) 0.0081(14) -0.0117(15) C3 0.0469(16) 0.077(2) 0.0434(16) 0.0108(15) -0.0022(13) -0.0223(15) C4 0.0378(15) 0.075(2) 0.083(2) 0.0246(17) 0.0160(15) 0.0162(14) C5 0.0475(16) 0.0591(18) 0.0653(19) -0.0021(15) 0.0095(14) -0.0004(14) C6 0.066(2) 0.063(2) 0.071(2) 0.0077(16) 0.0226(16) -0.0010(16) C7 0.0297(13) 0.0733(19) 0.0509(16) 0.0101(14) -0.0031(11) -0.0117(13) C8 0.0332(14) 0.0644(18) 0.0594(17) 0.0174(14) 0.0067(12) 0.0074(12) C9 0.0325(13) 0.0509(15) 0.0486(15) 0.0076(12) 0.0078(11) 0.0010(11) C10 0.0285(12) 0.0539(15) 0.0440(14) 0.0028(12) 0.0025(10) -0.0006(11) C11 0.0339(13) 0.0546(16) 0.0448(15) 0.0010(12) 0.0060(11) -0.0048(11) C12 0.0409(14) 0.0602(17) 0.0516(16) 0.0040(14) 0.0018(12) -0.0103(13) C13 0.0422(14) 0.0478(15) 0.0480(15) -0.0047(12) 0.0045(12) -0.0056(12) C14 0.0539(18) 0.068(2) 0.067(2) 0.0010(16) 0.0182(15) 0.0032(15) C15 0.069(2) 0.075(2) 0.082(2) -0.0134(19) 0.0160(18) 0.0160(18) C16 0.092(3) 0.051(2) 0.089(3) -0.0078(18) 0.004(2) 0.0140(18) C17 0.097(3) 0.052(2) 0.099(3) 0.0132(19) 0.024(2) -0.0031(19) C18 0.068(2) 0.0577(19) 0.076(2) 0.0042(16) 0.0258(17) -0.0040(15) C19 0.0384(14) 0.0497(15) 0.0531(16) 0.0099(12) 0.0078(12) 0.0062(12) C20 0.0518(18) 0.0585(19) 0.121(3) -0.0059(19) 0.0331(19) 0.0027(15) C21 0.075(2) 0.062(2) 0.138(4) -0.016(2) 0.045(2) 0.0069(18) C22 0.076(2) 0.0491(18) 0.079(2) -0.0013(16) 0.0142(18) -0.0022(15) C23 0.0525(17) 0.063(2) 0.080(2) -0.0002(16) 0.0154(16) -0.0093(15) C24 0.0458(16) 0.0585(18) 0.071(2) -0.0029(15) 0.0177(14) -0.0023(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.326(4) . ? N1 C5 1.326(4) . ? N2 C6 1.193(4) . ? N2 C7 1.451(4) . ? O1 C10 1.360(3) . ? C1 C2 1.361(4) . ? C2 C3 1.354(4) . ? C3 C4 1.386(5) . ? C3 C6 1.510(4) . ? C4 C5 1.410(4) . ? C7 C12 1.375(4) . ? C7 C8 1.385(4) . ? C8 C9 1.404(4) . ? C9 C10 1.401(4) . ? C9 C19 1.476(4) . ? C10 C11 1.396(4) . ? C11 C12 1.390(4) . ? C11 C13 1.486(4) . ? C13 C18 1.380(4) . ? C13 C14 1.387(4) . ? C14 C15 1.377(5) . ? C15 C16 1.366(5) . ? C16 C17 1.368(5) . ? C17 C18 1.374(5) . ? C19 C20 1.381(4) . ? C19 C24 1.390(4) . ? C20 C21 1.366(5) . ? C21 C22 1.370(5) . ? C22 C23 1.365(5) . ? C23 C24 1.374(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 C1 N1 C5 116.8(2) . . ? C6 N2 C7 120.2(3) . . ? N1 C1 C2 124.7(3) . . ? C3 C2 C1 119.5(3) . . ? C2 C3 C4 118.0(3) . . ? C2 C3 C6 119.5(3) . . ? C4 C3 C6 122.5(3) . . ? C3 C4 C5 118.8(3) . . ? N1 C5 C4 122.1(3) . . ? N2 C6 C3 119.7(3) . . ? C12 C7 C8 118.3(2) . . ? C12 C7 N2 114.4(3) . . ? C8 C7 N2 127.2(3) . . ? C7 C8 C9 122.2(3) . . ? C10 C9 C8 117.6(2) . . ? C10 C9 C19 122.7(2) . . ? C8 C9 C19 119.7(2) . . ? O1 C10 C11 122.2(2) . . ? O1 C10 C9 116.6(2) . . ? C11 C10 C9 121.1(2) . . ? C12 C11 C10 118.6(2) . . ? C12 C11 C13 118.4(2) . . ? C10 C11 C13 122.9(2) . . ? C7 C12 C11 122.2(3) . . ? C18 C13 C14 118.1(3) . . ? C18 C13 C11 119.4(3) . . ? C14 C13 C11 122.4(3) . . ? C15 C14 C13 120.8(3) . . ? C16 C15 C14 120.1(3) . . ? C15 C16 C17 119.9(3) . . ? C16 C17 C18 120.2(4) . . ? C17 C18 C13 120.9(3) . . ? C20 C19 C24 116.9(3) . . ? C20 C19 C9 119.5(2) . . ? C24 C19 C9 123.5(2) . . ? C21 C20 C19 121.5(3) . . ? C20 C21 C22 120.9(3) . . ? C23 C22 C21 118.7(3) . . ? C22 C23 C24 120.8(3) . . ? C23 C24 C19 121.2(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.786 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.043 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 712728' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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 p21/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 11.737(2) _cell_length_b 7.473(2) _cell_length_c 13.759(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.814(4) _cell_angle_gamma 90.00 _cell_volume 1104.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 800 _cell_measurement_theta_min 4 _cell_measurement_theta_max 18 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5981 _exptl_absorpt_correction_T_max 0.7443 _exptl_absorpt_process_details 'SADABS procedure' _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 'APEX diffractometer' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.2 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5973 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 18.91 _reflns_number_total 879 _reflns_number_gt 713 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+1.3511P] 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 879 _refine_ls_number_parameters 146 _refine_ls_number_restraints 38 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1477 _refine_ls_wR_factor_gt 0.1370 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.002 _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 -0.4393(4) 0.2994(5) -0.3087(3) 0.0630(12) Uani 1 1 d U . . N2 N -0.0572(5) 0.2649(6) 0.0310(4) 0.0803(14) Uani 1 1 d U . . O1 O 0.3739(4) 0.3347(5) 0.4856(3) 0.1218(18) Uani 1 1 d U . . H1O H 0.4374 0.3200 0.5395 0.183 Uiso 1 1 calc R . . C1 C -0.3266(5) 0.3642(6) -0.2841(4) 0.0637(14) Uani 1 1 d U . . H1 H -0.3093 0.4198 -0.3371 0.076 Uiso 1 1 calc R . . C2 C -0.2330(4) 0.3532(6) -0.1833(4) 0.0628(14) Uani 1 1 d U . . H2 H -0.1541 0.3988 -0.1688 0.075 Uiso 1 1 calc R . . C3 C -0.2595(5) 0.2732(6) -0.1050(4) 0.0590(14) Uani 1 1 d U . . C4 C -0.3766(5) 0.2108(7) -0.1307(4) 0.0692(15) Uani 1 1 d U . . H4 H -0.3983 0.1587 -0.0792 0.083 Uiso 1 1 calc R . . C5 C -0.4609(4) 0.2252(7) -0.2315(5) 0.0658(15) Uani 1 1 d U . . H5 H -0.5401 0.1793 -0.2476 0.079 Uiso 1 1 calc R . . C6 C -0.1631(6) 0.2450(7) 0.0097(5) 0.0800(17) Uani 1 1 d U . . H6 H -0.1896 0.2119 0.0624 0.096 Uiso 1 1 calc R . . C7 C 0.0302(4) 0.2375(6) 0.1418(4) 0.0548(13) Uani 1 1 d U . . C8 C 0.1393(5) 0.1558(6) 0.1550(4) 0.0604(14) Uani 1 1 d U . . H8 H 0.1526 0.1164 0.0963 0.072 Uiso 1 1 calc R . . C9 C 0.2292(4) 0.1321(6) 0.2553(4) 0.0581(13) Uani 1 1 d U . . H9 H 0.3022 0.0725 0.2639 0.070 Uiso 1 1 calc R . . C10 C 0.2146(4) 0.1941(6) 0.3436(4) 0.0543(13) Uani 1 1 d U . . C11 C 0.1044(5) 0.2783(6) 0.3281(4) 0.0613(14) Uani 1 1 d U . . H11 H 0.0924 0.3219 0.3866 0.074 Uiso 1 1 calc R . . C12 C 0.0119(4) 0.2995(6) 0.2287(4) 0.0592(14) Uani 1 1 d U . . H12 H -0.0625 0.3552 0.2200 0.071 Uiso 1 1 calc R . . C13 C 0.3155(5) 0.1746(7) 0.4529(4) 0.0882(18) Uani 1 1 d U . . H13A H 0.2799 0.1351 0.5017 0.106 Uiso 1 1 calc R . . H13B H 0.3752 0.0853 0.4522 0.106 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 0.058(3) 0.060(3) 0.051(3) 0.002(2) 0.000(2) 0.003(2) N2 0.071(3) 0.068(3) 0.089(3) -0.018(2) 0.019(3) -0.008(3) O1 0.136(4) 0.079(3) 0.072(3) 0.008(2) -0.039(2) -0.025(3) C1 0.078(4) 0.059(3) 0.057(3) 0.007(3) 0.030(3) 0.000(3) C2 0.039(3) 0.061(3) 0.077(4) -0.014(3) 0.012(3) -0.007(2) C3 0.062(4) 0.058(3) 0.038(3) -0.003(2) 0.000(3) 0.015(3) C4 0.077(4) 0.067(4) 0.062(4) 0.009(3) 0.027(3) 0.004(3) C5 0.044(3) 0.063(3) 0.083(4) -0.001(3) 0.018(3) -0.002(3) C6 0.078(4) 0.070(4) 0.096(4) -0.005(3) 0.039(4) 0.004(3) C7 0.057(3) 0.051(3) 0.039(3) -0.003(2) 0.000(3) -0.004(2) C8 0.065(3) 0.063(3) 0.050(3) -0.005(3) 0.020(3) 0.005(3) C9 0.047(3) 0.056(3) 0.066(3) 0.001(3) 0.017(3) 0.002(2) C10 0.051(3) 0.049(3) 0.045(3) 0.000(2) 0.001(3) -0.004(2) C11 0.073(4) 0.065(3) 0.043(3) -0.005(2) 0.020(3) 0.007(3) C12 0.043(3) 0.060(3) 0.067(3) 0.001(3) 0.014(3) 0.008(2) C13 0.093(4) 0.065(4) 0.063(3) 0.002(3) -0.014(3) -0.003(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 C5 1.310(6) . ? N1 C1 1.319(6) . ? N2 C6 1.165(6) . ? N2 C7 1.468(6) . ? O1 C13 1.362(6) . ? C1 C2 1.381(6) . ? C2 C3 1.373(6) . ? C3 C4 1.356(6) . ? C3 C6 1.541(7) . ? C4 C5 1.344(7) . ? C7 C8 1.363(6) . ? C7 C12 1.378(6) . ? C8 C9 1.368(6) . ? C9 C10 1.374(6) . ? C10 C11 1.376(6) . ? C10 C13 1.499(6) . ? C11 C12 1.369(6) . ? 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 C5 N1 C1 116.7(4) . . ? C6 N2 C7 118.1(5) . . ? N1 C1 C2 123.0(4) . . ? C3 C2 C1 118.2(4) . . ? C4 C3 C2 118.2(4) . . ? C4 C3 C6 117.9(5) . . ? C2 C3 C6 123.9(5) . . ? C5 C4 C3 119.2(5) . . ? N1 C5 C4 124.6(5) . . ? N2 C6 C3 120.5(6) . . ? C8 C7 C12 120.1(4) . . ? C8 C7 N2 115.2(4) . . ? C12 C7 N2 124.5(5) . . ? C7 C8 C9 119.5(4) . . ? C8 C9 C10 121.8(4) . . ? C9 C10 C11 117.6(4) . . ? C9 C10 C13 121.6(5) . . ? C11 C10 C13 120.8(5) . . ? C12 C11 C10 121.6(4) . . ? C11 C12 C7 119.3(4) . . ? O1 C13 C10 109.5(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 18.91 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.415 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.034 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 712729' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N2 O2' _chemical_formula_weight 244.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p21/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 10.913(4) _cell_length_b 8.774(3) _cell_length_c 14.000(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.55(2) _cell_angle_gamma 90.00 _cell_volume 1321.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6 _cell_measurement_theta_max 16 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'Siemens AED diffractometer' _diffrn_measurement_method '\q/2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7474 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 30.05 _reflns_number_total 3863 _reflns_number_gt 2365 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3863 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1446 _refine_ls_wR_factor_gt 0.1276 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.68183(10) 0.64746(14) -0.16592(8) 0.0565(3) Uani 1 1 d . . . N2 N 1.23542(13) 0.8962(2) 0.36960(10) 0.0684(4) Uani 1 1 d . . . O1 O 0.44795(11) 0.71807(16) -0.49995(8) 0.0876(4) Uani 1 1 d . . . O2 O 0.83993(8) 0.66399(12) 0.01614(6) 0.0580(3) Uani 1 1 d . . . H2O H 0.7940 0.6573 -0.0363 0.087 Uiso 1 1 calc R . . C1 C 0.71052(12) 0.70567(16) -0.24756(11) 0.0568(4) Uani 1 1 d . . . H1 H 0.7884 0.7499 -0.2450 0.068 Uiso 1 1 calc R . . C2 C 0.63174(12) 0.70412(15) -0.33517(10) 0.0505(3) Uani 1 1 d . . . H2 H 0.6555 0.7480 -0.3897 0.061 Uiso 1 1 calc R . . C3 C 0.51594(10) 0.63568(13) -0.34046(9) 0.0403(3) Uani 1 1 d . . . C4 C 0.48642(11) 0.57215(16) -0.25697(10) 0.0495(3) Uani 1 1 d . . . H4 H 0.4106 0.5233 -0.2579 0.059 Uiso 1 1 calc R . . C5 C 0.57123(13) 0.58204(17) -0.17177(10) 0.0574(4) Uani 1 1 d . . . H5 H 0.5495 0.5406 -0.1158 0.069 Uiso 1 1 calc R . . C6 C 0.42744(11) 0.63505(16) -0.43545(10) 0.0502(3) Uani 1 1 d . . . C7 C 0.31818(12) 0.53110(18) -0.44799(12) 0.0624(4) Uani 1 1 d . . . H7A H 0.2733 0.5403 -0.5128 0.094 Uiso 1 1 calc R . . H7B H 0.2648 0.5581 -0.4027 0.094 Uiso 1 1 calc R . . H7C H 0.3460 0.4279 -0.4366 0.094 Uiso 1 1 calc R . . C8 C 1.16641(10) 0.85183(15) 0.28200(9) 0.0456(3) Uani 1 1 d . . . C9 C 1.06585(11) 0.93953(15) 0.23815(10) 0.0510(3) Uani 1 1 d . . . H9 H 1.0433 1.0263 0.2692 0.061 Uiso 1 1 calc R . . C10 C 0.99956(11) 0.89872(15) 0.14903(10) 0.0501(3) Uani 1 1 d . . . H10 H 0.9325 0.9586 0.1216 0.060 Uiso 1 1 calc R . . C11 C 1.02974(10) 0.77141(14) 0.09917(9) 0.0440(3) Uani 1 1 d . . . C12 C 1.12979(11) 0.68513(14) 0.14321(10) 0.0476(3) Uani 1 1 d . . . H12 H 1.1524 0.5989 0.1116 0.057 Uiso 1 1 calc R . . C13 C 1.19711(11) 0.72324(14) 0.23270(9) 0.0472(3) Uani 1 1 d . . . H13 H 1.2635 0.6624 0.2602 0.057 Uiso 1 1 calc R . . C14 C 0.95513(12) 0.72861(18) 0.00269(9) 0.0567(4) Uani 1 1 d . . . H14A H 0.9403 0.8184 -0.0380 0.068 Uiso 1 1 calc R . . H14B H 1.0012 0.6557 -0.0295 0.068 Uiso 1 1 calc R . . H2NB H 1.2050(14) 0.970(2) 0.4018(12) 0.066(5) Uiso 1 1 d . . . H2NA H 1.2901(17) 0.835(2) 0.4007(13) 0.080(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 N1 0.0513(6) 0.0623(7) 0.0507(7) -0.0093(6) -0.0066(5) 0.0062(5) N2 0.0606(8) 0.0877(10) 0.0517(7) -0.0178(7) -0.0061(6) 0.0090(7) O1 0.0794(7) 0.1164(10) 0.0596(7) 0.0351(7) -0.0105(6) -0.0116(7) O2 0.0495(5) 0.0749(6) 0.0448(5) 0.0017(5) -0.0064(4) -0.0117(5) C1 0.0418(6) 0.0615(8) 0.0644(9) -0.0122(7) 0.0011(6) -0.0094(6) C2 0.0504(7) 0.0516(7) 0.0494(7) -0.0011(6) 0.0081(6) -0.0087(6) C3 0.0375(6) 0.0402(6) 0.0420(6) -0.0019(5) 0.0031(5) 0.0031(4) C4 0.0396(6) 0.0586(8) 0.0496(7) 0.0035(6) 0.0050(5) -0.0031(5) C5 0.0547(7) 0.0727(9) 0.0433(7) 0.0044(7) 0.0040(6) 0.0032(7) C6 0.0457(7) 0.0571(7) 0.0453(7) -0.0016(6) -0.0002(5) 0.0080(6) C7 0.0493(7) 0.0729(9) 0.0601(8) -0.0169(8) -0.0055(6) -0.0024(7) C8 0.0388(6) 0.0550(7) 0.0424(7) -0.0008(6) 0.0046(5) -0.0053(5) C9 0.0438(6) 0.0514(7) 0.0576(8) -0.0102(6) 0.0079(6) 0.0046(5) C10 0.0373(6) 0.0537(7) 0.0569(8) 0.0034(6) 0.0008(5) 0.0062(5) C11 0.0391(6) 0.0502(7) 0.0419(6) 0.0025(5) 0.0043(5) -0.0072(5) C12 0.0479(6) 0.0402(6) 0.0535(8) -0.0043(6) 0.0053(5) -0.0012(5) C13 0.0419(6) 0.0439(6) 0.0529(7) 0.0052(6) -0.0008(5) 0.0034(5) C14 0.0517(7) 0.0749(9) 0.0419(7) 0.0008(7) 0.0033(6) -0.0098(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.3267(19) . ? N1 C1 1.3357(19) . ? N2 C8 1.3842(18) . ? O1 C6 1.2096(17) . ? O2 C14 1.4199(16) . ? C1 C2 1.3762(18) . ? C2 C3 1.3900(17) . ? C3 C4 1.3805(19) . ? C3 C6 1.5083(18) . ? C4 C5 1.3858(19) . ? C6 C7 1.488(2) . ? C8 C13 1.3922(18) . ? C8 C9 1.3963(18) . ? C9 C10 1.382(2) . ? C10 C11 1.3856(19) . ? C11 C12 1.3863(18) . ? C11 C14 1.5045(18) . ? C12 C13 1.3842(18) . ? 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 C5 N1 C1 116.92(11) . . ? N1 C1 C2 123.94(12) . . ? C1 C2 C3 118.67(12) . . ? C4 C3 C2 117.85(12) . . ? C4 C3 C6 122.67(11) . . ? C2 C3 C6 119.48(12) . . ? C3 C4 C5 119.16(12) . . ? N1 C5 C4 123.43(13) . . ? O1 C6 C7 121.66(13) . . ? O1 C6 C3 119.03(12) . . ? C7 C6 C3 119.31(12) . . ? N2 C8 C13 121.78(13) . . ? N2 C8 C9 120.47(13) . . ? C13 C8 C9 117.70(11) . . ? C10 C9 C8 120.65(12) . . ? C9 C10 C11 122.09(12) . . ? C10 C11 C12 116.85(11) . . ? C10 C11 C14 121.00(12) . . ? C12 C11 C14 122.14(12) . . ? C13 C12 C11 122.09(12) . . ? C12 C13 C8 120.62(11) . . ? O2 C14 C11 109.87(11) . . ? 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 O2 H2O N1 0.82 2.01 2.8346(17) 178.3 . N2 H2NB O2 0.883(18) 2.157(19) 3.032(2) 171.0(14) 2_755 N2 H2NA O1 0.863(18) 2.273(19) 3.123(2) 168.4(16) 1_656 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.130 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.053 #===END data_7 _database_code_depnum_ccdc_archive 'CCDC 712730' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N O' _chemical_formula_weight 261.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p21/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 11.3071(14) _cell_length_b 17.413(2) _cell_length_c 7.2568(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.005(2) _cell_angle_gamma 90.00 _cell_volume 1402.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 800 _cell_measurement_theta_min 4 _cell_measurement_theta_max 18 _exptl_crystal_description prism _exptl_crystal_colour violet _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.762934 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS procedure' _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 'SMART diffractometer' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.2 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13177 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 24.77 _reflns_number_total 2409 _reflns_number_gt 1811 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+0.1091P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2409 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 -0.08173(15) -0.82356(9) 0.93342(17) 0.0492(4) Uani 1 1 d . . . O1 O 0.07365(9) -0.88425(7) 0.25851(14) 0.0505(3) Uani 1 1 d . . . H1O H 0.0189 -0.8762 0.1688 0.076 Uiso 1 1 calc R . . C1 C 0.03234(13) -0.87274(8) 0.42269(19) 0.0388(3) Uani 1 1 d . . . C2 C 0.11532(12) -0.84587(8) 0.57910(19) 0.0391(3) Uani 1 1 d . . . C3 C 0.07401(13) -0.82851(8) 0.74383(19) 0.0407(3) Uani 1 1 d . . . H3 H 0.1281 -0.8096 0.8466 0.049 Uiso 1 1 calc R . . C4 C -0.04612(13) -0.83883(8) 0.75828(19) 0.0396(3) Uani 1 1 d . . . C5 C -0.12548(13) -0.86848(8) 0.6053(2) 0.0408(3) Uani 1 1 d . . . H5 H -0.2051 -0.8773 0.6153 0.049 Uiso 1 1 calc R . . C6 C -0.08885(12) -0.88558(8) 0.43573(19) 0.0383(3) Uani 1 1 d . . . C7 C 0.24639(13) -0.83787(9) 0.57632(19) 0.0443(4) Uani 1 1 d . . . C8 C 0.30999(15) -0.89646(10) 0.5059(2) 0.0568(4) Uani 1 1 d . . . H8 H 0.2695 -0.9401 0.4536 0.068 Uiso 1 1 calc R . . C9 C 0.43343(17) -0.88974(13) 0.5137(3) 0.0724(6) Uani 1 1 d . . . H9 H 0.4752 -0.9289 0.4668 0.087 Uiso 1 1 calc R . . C10 C 0.49412(17) -0.82501(15) 0.5912(3) 0.0771(6) Uani 1 1 d . . . H10 H 0.5768 -0.8209 0.5973 0.093 Uiso 1 1 calc R . . C11 C 0.43292(17) -0.76714(14) 0.6588(3) 0.0724(6) Uani 1 1 d . . . H11 H 0.4740 -0.7234 0.7091 0.087 Uiso 1 1 calc R . . C12 C 0.30988(15) -0.77320(11) 0.6530(2) 0.0546(4) Uani 1 1 d . . . H12 H 0.2694 -0.7337 0.7008 0.066 Uiso 1 1 calc R . . C13 C -0.17828(13) -0.91521(8) 0.2722(2) 0.0411(4) Uani 1 1 d . . . C14 C -0.15394(15) -0.97994(9) 0.1725(2) 0.0494(4) Uani 1 1 d . . . H14 H -0.0813 -1.0058 0.2093 0.059 Uiso 1 1 calc R . . C15 C -0.23657(16) -1.00625(10) 0.0193(3) 0.0616(5) Uani 1 1 d . . . H15 H -0.2190 -1.0494 -0.0462 0.074 Uiso 1 1 calc R . . C16 C -0.34493(17) -0.96845(13) -0.0361(3) 0.0711(6) Uani 1 1 d . . . H16 H -0.4003 -0.9861 -0.1389 0.085 Uiso 1 1 calc R . . C17 C -0.37095(16) -0.90472(12) 0.0605(3) 0.0716(6) Uani 1 1 d . . . H17 H -0.4439 -0.8793 0.0228 0.086 Uiso 1 1 calc R . . C18 C -0.28867(14) -0.87824(11) 0.2144(2) 0.0556(4) Uani 1 1 d . . . H18 H -0.3073 -0.8354 0.2797 0.067 Uiso 1 1 calc R . . H1NB H -0.1600(19) -0.8332(11) 0.930(3) 0.073(6) Uiso 1 1 d . . . H1NA H -0.0633(17) -0.7755(12) 0.972(3) 0.074(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 N1 0.0591(9) 0.0544(9) 0.0374(7) -0.0035(6) 0.0176(6) -0.0030(7) O1 0.0462(6) 0.0728(7) 0.0342(5) -0.0046(5) 0.0123(4) 0.0015(5) C1 0.0442(8) 0.0402(8) 0.0334(7) 0.0018(6) 0.0112(6) 0.0033(6) C2 0.0422(8) 0.0395(8) 0.0355(7) 0.0043(6) 0.0073(6) 0.0012(6) C3 0.0480(8) 0.0397(8) 0.0332(7) 0.0006(6) 0.0049(6) -0.0018(6) C4 0.0516(9) 0.0367(8) 0.0325(7) 0.0027(6) 0.0129(6) 0.0025(6) C5 0.0410(8) 0.0438(8) 0.0395(8) 0.0028(6) 0.0124(6) 0.0003(6) C6 0.0428(8) 0.0379(8) 0.0348(7) 0.0008(6) 0.0091(6) 0.0003(6) C7 0.0445(8) 0.0556(9) 0.0328(7) 0.0062(7) 0.0073(6) 0.0006(7) C8 0.0525(10) 0.0614(11) 0.0566(10) 0.0042(8) 0.0107(8) 0.0084(8) C9 0.0541(11) 0.0961(15) 0.0693(13) 0.0127(11) 0.0176(9) 0.0219(11) C10 0.0426(10) 0.132(2) 0.0558(11) 0.0081(12) 0.0074(8) -0.0050(12) C11 0.0581(11) 0.1127(17) 0.0466(10) -0.0085(10) 0.0102(8) -0.0283(11) C12 0.0518(9) 0.0749(12) 0.0378(8) -0.0062(8) 0.0103(7) -0.0119(8) C13 0.0429(8) 0.0467(8) 0.0353(7) 0.0018(6) 0.0112(6) -0.0037(6) C14 0.0538(9) 0.0447(9) 0.0483(9) -0.0025(7) 0.0067(7) 0.0001(7) C15 0.0718(12) 0.0564(10) 0.0548(10) -0.0127(8) 0.0076(9) -0.0042(9) C16 0.0624(12) 0.0910(15) 0.0545(11) -0.0176(10) -0.0028(9) -0.0107(10) C17 0.0485(10) 0.1012(16) 0.0608(12) -0.0120(11) -0.0003(9) 0.0119(10) C18 0.0485(9) 0.0707(11) 0.0476(9) -0.0109(8) 0.0090(7) 0.0080(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 N1 C4 1.4295(18) . ? O1 C1 1.3749(17) . ? C1 C2 1.407(2) . ? C1 C6 1.409(2) . ? C2 C3 1.397(2) . ? C2 C7 1.493(2) . ? C3 C4 1.394(2) . ? C4 C5 1.387(2) . ? C5 C6 1.403(2) . ? C6 C13 1.496(2) . ? C7 C12 1.393(2) . ? C7 C8 1.400(2) . ? C8 C9 1.391(2) . ? C9 C10 1.382(3) . ? C10 C11 1.366(3) . ? C11 C12 1.388(2) . ? C13 C18 1.396(2) . ? C13 C14 1.395(2) . ? C14 C15 1.387(2) . ? C15 C16 1.381(3) . ? C16 C17 1.374(3) . ? C17 C18 1.388(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 117.57(12) . . ? O1 C1 C6 122.05(12) . . ? C2 C1 C6 120.37(12) . . ? C3 C2 C1 118.79(13) . . ? C3 C2 C7 119.11(12) . . ? C1 C2 C7 122.07(12) . . ? C4 C3 C2 121.76(13) . . ? C5 C4 C3 118.59(13) . . ? C5 C4 N1 122.14(13) . . ? C3 C4 N1 119.13(13) . . ? C4 C5 C6 121.79(13) . . ? C5 C6 C1 118.61(13) . . ? C5 C6 C13 120.04(12) . . ? C1 C6 C13 121.34(12) . . ? C12 C7 C8 118.26(15) . . ? C12 C7 C2 120.49(14) . . ? C8 C7 C2 121.16(14) . . ? C9 C8 C7 120.34(17) . . ? C10 C9 C8 120.12(19) . . ? C11 C10 C9 120.11(17) . . ? C10 C11 C12 120.44(19) . . ? C11 C12 C7 120.73(17) . . ? C18 C13 C14 118.05(14) . . ? C18 C13 C6 120.64(13) . . ? C14 C13 C6 121.31(13) . . ? C15 C14 C13 120.90(15) . . ? C16 C15 C14 120.03(17) . . ? C17 C16 C15 120.05(16) . . ? C16 C17 C18 120.17(17) . . ? C17 C18 C13 120.81(16) . . ? 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 H1O N1 0.82 2.08 2.8612(18) 160.2 1_554 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.77 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.124 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.030 #===END data_8 _database_code_depnum_ccdc_archive 'CCDC 712731' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H9 N O' _chemical_formula_weight 123.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 15.0879(7) _cell_length_b 7.4306(3) _cell_length_c 5.77510(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 647.46(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6 _cell_measurement_theta_max 16 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.687 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens AED diffractometer' _diffrn_measurement_method '\q/2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 677 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0104 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 5.87 _diffrn_reflns_theta_max 70.02 _reflns_number_total 677 _reflns_number_gt 617 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0973P)^2^+0.0143P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 677 _refine_ls_number_parameters 91 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1287 _refine_ls_wR_factor_gt 0.1261 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.074 _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 0.34884(16) 0.3279(3) -0.1853(6) 0.0559(6) Uani 1 1 d . . . O1 O 0.72145(11) 0.0235(2) 0.1786(7) 0.0707(7) Uani 1 1 d . . . H1 H 0.7006 -0.0761 0.2070 0.106 Uiso 1 1 calc R . . C1 C 0.67053(16) 0.1585(3) 0.2947(7) 0.0610(8) Uani 1 1 d . . . H1A H 0.7061 0.2665 0.3099 0.073 Uiso 1 1 calc R . . H1B H 0.6563 0.1166 0.4494 0.073 Uiso 1 1 calc R . . C2 C 0.58576(15) 0.2044(3) 0.1696(5) 0.0446(7) Uani 1 1 d . . . C3 C 0.58768(16) 0.2884(3) -0.0457(5) 0.0489(7) Uani 1 1 d . . . H3 H 0.6420 0.3156 -0.1132 0.059 Uiso 1 1 calc R . . C4 C 0.51088(16) 0.3321(3) -0.1602(5) 0.0471(7) Uani 1 1 d . . . H4 H 0.5139 0.3888 -0.3035 0.056 Uiso 1 1 calc R . . C5 C 0.42862(15) 0.2925(3) -0.0645(5) 0.0431(6) Uani 1 1 d . . . C6 C 0.42609(15) 0.2099(3) 0.1525(4) 0.0445(7) Uani 1 1 d . . . H6 H 0.3718 0.1837 0.2207 0.053 Uiso 1 1 calc R . . C7 C 0.50363(15) 0.1667(3) 0.2667(5) 0.0444(6) Uani 1 1 d . . . H7 H 0.5008 0.1114 0.4110 0.053 Uiso 1 1 calc R . . H1NA H 0.358(2) 0.407(6) -0.301(11) 0.109(13) Uiso 1 1 d . . . H1NB H 0.308(2) 0.368(5) -0.108(8) 0.076(11) 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 0.0559(12) 0.0490(11) 0.0629(14) 0.0042(12) -0.0069(12) 0.0040(9) O1 0.0495(9) 0.0569(10) 0.1058(17) 0.0117(13) 0.0130(11) 0.0047(8) C1 0.0495(13) 0.0554(14) 0.078(2) -0.0036(16) -0.0106(14) -0.0026(10) C2 0.0461(12) 0.0382(10) 0.0497(16) -0.0067(13) -0.0003(11) -0.0003(8) C3 0.0484(12) 0.0452(12) 0.0529(19) -0.0051(14) 0.0108(11) -0.0061(9) C4 0.0615(14) 0.0385(11) 0.0412(16) -0.0004(12) 0.0055(11) -0.0049(9) C5 0.0504(12) 0.0321(10) 0.0469(15) -0.0058(13) -0.0003(11) 0.0010(8) C6 0.0454(12) 0.0418(11) 0.0464(16) -0.0006(12) 0.0081(10) -0.0028(8) C7 0.0527(12) 0.0408(11) 0.0397(15) -0.0001(12) 0.0023(9) -0.0008(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 N1 C5 1.416(3) . ? O1 C1 1.430(4) . ? C1 C2 1.508(4) . ? C2 C7 1.389(3) . ? C2 C3 1.391(3) . ? C3 C4 1.373(4) . ? C4 C5 1.390(3) . ? C5 C6 1.396(3) . ? C6 C7 1.381(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 O1 C1 C2 112.9(3) . . ? C7 C2 C3 118.0(2) . . ? C7 C2 C1 121.2(3) . . ? C3 C2 C1 120.8(2) . . ? C4 C3 C2 121.3(2) . . ? C3 C4 C5 120.8(3) . . ? C4 C5 C6 118.3(2) . . ? C4 C5 N1 121.6(3) . . ? C6 C5 N1 120.0(2) . . ? C7 C6 C5 120.5(2) . . ? C6 C7 C2 121.1(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 70.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.160 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.043