# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 920705' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H15 N O2' _chemical_formula_sum 'C16 H15 N O2' _chemical_formula_weight 253.29 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.6796(4) _cell_length_b 21.6754(14) _cell_length_c 9.7556(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.919(2) _cell_angle_gamma 90.00 _cell_volume 1407.24(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12782 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 27.33 _exptl_crystal_description . _exptl_crystal_colour . _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8167 _exptl_absorpt_correction_T_max 0.9968 _exptl_absorpt_process_details 'Absorption was corrected by ABSCOR' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Area Detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23644 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 27.40 _reflns_number_total 3196 _reflns_number_gt 1626 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0651P)^2^+0.0427P] 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 3196 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1012 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1067 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.12373(19) 0.15160(6) 0.42154(14) 0.0516(4) Uani 1 1 d . . . H1 H 0.0044 0.1522 0.4484 0.062 Uiso 1 1 calc R . . O1 O 0.42110(17) 0.09919(5) 0.45073(13) 0.0595(4) Uani 1 1 d . . . O2 O 0.24311(17) 0.33833(6) 0.04327(14) 0.0699(4) Uani 1 1 d . . . H2O H 0.1428 0.3602 0.0315 0.105 Uiso 1 1 calc R . . C1 C 0.1638(3) -0.01993(7) 0.74417(19) 0.0563(4) Uani 1 1 d . . . C11 C 0.3425(2) 0.20475(8) 0.26506(19) 0.0558(5) Uani 1 1 d . . . H11 H 0.4476 0.1774 0.2869 0.067 Uiso 1 1 calc R . . C7 C 0.2432(3) 0.02069(8) 0.64221(19) 0.0568(5) Uani 1 1 d . . . H7 H 0.3755 0.0138 0.6231 0.068 Uiso 1 1 calc R . . C8 C 0.1465(3) 0.06641(7) 0.57384(18) 0.0520(4) Uani 1 1 d . . . H8 H 0.0125 0.0735 0.5880 0.062 Uiso 1 1 calc R . . C12 C 0.3650(2) 0.25171(8) 0.17155(19) 0.0583(5) Uani 1 1 d . . . H12 H 0.4855 0.2556 0.1311 0.070 Uiso 1 1 calc R . . C10 C 0.1636(2) 0.19840(7) 0.32635(17) 0.0485(4) Uani 1 1 d . . . C9 C 0.2432(2) 0.10611(7) 0.47696(17) 0.0493(4) Uani 1 1 d . . . C14 C 0.0337(3) 0.28713(8) 0.1991(2) 0.0627(5) Uani 1 1 d . . . H14 H -0.0706 0.3149 0.1779 0.075 Uiso 1 1 calc R . . C13 C 0.2109(2) 0.29300(7) 0.13723(18) 0.0532(4) Uani 1 1 d . . . C15 C 0.0106(3) 0.24027(8) 0.29222(19) 0.0613(5) Uani 1 1 d . . . H15 H -0.1098 0.2367 0.3328 0.074 Uiso 1 1 calc R . . C2 C -0.0312(3) -0.01601(8) 0.7826(2) 0.0610(5) Uani 1 1 d . . . H2 H -0.1188 0.0130 0.7407 0.073 Uiso 1 1 calc R . . C6 C 0.2875(3) -0.06479(9) 0.8095(2) 0.0786(6) Uani 1 1 d . . . H6 H 0.4185 -0.0692 0.7854 0.094 Uiso 1 1 calc R . . C3 C -0.0971(3) -0.05469(9) 0.8822(2) 0.0707(6) Uani 1 1 d . . . H3 H -0.2285 -0.0511 0.9059 0.085 Uiso 1 1 calc R . . C4 C 0.0278(4) -0.09872(9) 0.9478(2) 0.0765(6) Uani 1 1 d . . . C5 C 0.2196(4) -0.10281(10) 0.9091(2) 0.0890(7) Uani 1 1 d . . . H5 H 0.3065 -0.1320 0.9510 0.107 Uiso 1 1 calc R . . C16 C -0.0467(5) -0.14020(11) 1.0575(2) 0.1081(9) Uani 1 1 d . . . H16A H -0.1871 -0.1328 1.0644 0.162 Uiso 1 1 calc R . . H16B H 0.0268 -0.1316 1.1443 0.162 Uiso 1 1 calc R . . H16C H -0.0270 -0.1826 1.0332 0.162 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 0.0418(7) 0.0539(8) 0.0615(9) 0.0002(7) 0.0179(6) 0.0001(6) O1 0.0454(7) 0.0624(7) 0.0728(9) -0.0030(6) 0.0168(6) 0.0012(5) O2 0.0484(7) 0.0812(8) 0.0831(10) 0.0266(7) 0.0230(6) 0.0065(6) C1 0.0620(11) 0.0534(10) 0.0534(11) -0.0034(8) 0.0051(9) 0.0019(8) C11 0.0424(10) 0.0621(10) 0.0649(12) 0.0035(9) 0.0163(8) 0.0051(7) C7 0.0528(10) 0.0599(10) 0.0585(11) -0.0061(9) 0.0109(8) 0.0007(8) C8 0.0466(9) 0.0541(9) 0.0564(10) -0.0030(8) 0.0102(8) -0.0014(8) C12 0.0426(10) 0.0684(11) 0.0667(12) 0.0069(10) 0.0208(8) 0.0014(8) C10 0.0438(9) 0.0508(9) 0.0526(10) -0.0025(8) 0.0133(8) -0.0031(7) C9 0.0445(10) 0.0505(9) 0.0538(11) -0.0099(8) 0.0099(8) -0.0031(7) C14 0.0439(10) 0.0727(12) 0.0742(13) 0.0162(10) 0.0201(9) 0.0101(8) C13 0.0444(9) 0.0597(10) 0.0569(11) 0.0063(9) 0.0132(8) -0.0025(7) C15 0.0445(10) 0.0718(11) 0.0709(12) 0.0087(10) 0.0235(9) 0.0051(8) C2 0.0636(12) 0.0618(11) 0.0575(12) 0.0035(9) 0.0040(9) -0.0039(9) C6 0.0821(14) 0.0761(13) 0.0785(15) 0.0085(12) 0.0119(12) 0.0194(11) C3 0.0809(14) 0.0744(13) 0.0577(12) -0.0036(10) 0.0115(10) -0.0162(11) C4 0.1181(19) 0.0586(12) 0.0527(12) -0.0007(10) 0.0062(12) -0.0120(12) C5 0.118(2) 0.0727(14) 0.0762(16) 0.0132(12) 0.0059(15) 0.0178(13) C16 0.174(3) 0.0819(15) 0.0684(15) 0.0154(12) 0.0138(16) -0.0271(16) _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 C9 1.352(2) . ? N1 C10 1.416(2) . ? N1 H1 0.8600 . ? O1 C9 1.2459(18) . ? O2 C13 1.3733(19) . ? O2 H2O 0.8200 . ? C1 C2 1.388(3) . ? C1 C6 1.394(3) . ? C1 C7 1.462(3) . ? C11 C12 1.383(2) . ? C11 C10 1.388(2) . ? C11 H11 0.9300 . ? C7 C8 1.330(2) . ? C7 H7 0.9300 . ? C8 C9 1.468(2) . ? C8 H8 0.9300 . ? C12 C13 1.383(2) . ? C12 H12 0.9300 . ? C10 C15 1.386(2) . ? C14 C13 1.380(2) . ? C14 C15 1.380(2) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C2 C3 1.384(3) . ? C2 H2 0.9300 . ? C6 C5 1.380(3) . ? C6 H6 0.9300 . ? C3 C4 1.387(3) . ? C3 H3 0.9300 . ? C4 C5 1.369(3) . ? C4 C16 1.514(3) . ? C5 H5 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C10 130.33(13) . . ? C9 N1 H1 114.8 . . ? C10 N1 H1 114.8 . . ? C13 O2 H2O 109.5 . . ? C2 C1 C6 116.89(18) . . ? C2 C1 C7 123.41(16) . . ? C6 C1 C7 119.70(17) . . ? C12 C11 C10 120.18(15) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C8 C7 C1 126.92(17) . . ? C8 C7 H7 116.5 . . ? C1 C7 H7 116.5 . . ? C7 C8 C9 122.54(16) . . ? C7 C8 H8 118.7 . . ? C9 C8 H8 118.7 . . ? C13 C12 C11 121.01(15) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C15 C10 C11 118.42(15) . . ? C15 C10 N1 116.78(14) . . ? C11 C10 N1 124.80(15) . . ? O1 C9 N1 123.12(15) . . ? O1 C9 C8 122.79(15) . . ? N1 C9 C8 114.08(14) . . ? C13 C14 C15 120.27(16) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? O2 C13 C14 123.18(15) . . ? O2 C13 C12 117.94(14) . . ? C14 C13 C12 118.88(16) . . ? C14 C15 C10 121.23(16) . . ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.4 . . ? C3 C2 C1 120.97(18) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C5 C6 C1 121.4(2) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? C2 C3 C4 121.7(2) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 117.2(2) . . ? C5 C4 C16 121.9(2) . . ? C3 C4 C16 120.9(2) . . ? C4 C5 C6 121.8(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C4 C16 H16A 109.5 . . ? C4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C7 C8 0.8(3) . . . . ? C6 C1 C7 C8 -178.26(17) . . . . ? C1 C7 C8 C9 177.62(16) . . . . ? C10 C11 C12 C13 -0.1(3) . . . . ? C12 C11 C10 C15 -0.5(3) . . . . ? C12 C11 C10 N1 179.02(15) . . . . ? C9 N1 C10 C15 -177.75(16) . . . . ? C9 N1 C10 C11 2.7(3) . . . . ? C10 N1 C9 O1 1.1(3) . . . . ? C10 N1 C9 C8 179.58(15) . . . . ? C7 C8 C9 O1 1.0(3) . . . . ? C7 C8 C9 N1 -177.45(15) . . . . ? C15 C14 C13 O2 179.65(17) . . . . ? C15 C14 C13 C12 -0.8(3) . . . . ? C11 C12 C13 O2 -179.74(16) . . . . ? C11 C12 C13 C14 0.7(3) . . . . ? C13 C14 C15 C10 0.3(3) . . . . ? C11 C10 C15 C14 0.4(3) . . . . ? N1 C10 C15 C14 -179.17(16) . . . . ? C6 C1 C2 C3 0.7(3) . . . . ? C7 C1 C2 C3 -178.39(17) . . . . ? C2 C1 C6 C5 -0.9(3) . . . . ? C7 C1 C6 C5 178.14(19) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C2 C3 C4 C16 179.46(19) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C16 C4 C5 C6 -179.7(2) . . . . ? C1 C6 C5 C4 0.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.143 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.033 data_2 _database_code_depnum_ccdc_archive 'CCDC 920706' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 N O2' _chemical_formula_weight 253.29 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 ? _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.1644(15) _cell_length_b 17.790(4) _cell_length_c 10.796(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.590(5) _cell_angle_gamma 90.00 _cell_volume 1366.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9682 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details 'Absorption was corrected by ABSCOR' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 13037 _diffrn_reflns_av_R_equivalents 0.0944 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3109 _reflns_number_gt 1373 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0790P)^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 3109 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1505 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1871 _refine_ls_wR_factor_gt 0.1435 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 O2 O 0.6961(2) 0.63590(11) 0.42084(17) 0.0788(6) Uani 1 1 d . . . H2O H 0.5949 0.6185 0.4354 0.118 Uiso 1 1 calc R . . O1 O 0.8852(2) 0.89546(10) 0.03029(16) 0.0713(5) Uani 1 1 d . . . C1 C 0.6654(4) 1.04268(15) -0.2680(2) 0.0679(7) Uani 1 1 d . . . C2 C 0.7949(5) 1.08858(18) -0.3176(3) 0.0902(9) Uani 1 1 d . . . H2 H 0.9193 1.0894 -0.2818 0.108 Uiso 1 1 calc R . . C3 C 0.7388(6) 1.1332(2) -0.4206(4) 0.1088(12) Uani 1 1 d . . . H3 H 0.8253 1.1641 -0.4538 0.131 Uiso 1 1 calc R . . C4 C 0.5570(6) 1.13165(19) -0.4728(3) 0.0957(10) Uani 1 1 d . . . H4 H 0.5214 1.1618 -0.5418 0.115 Uiso 1 1 calc R . . C5 C 0.4233(4) 1.08691(17) -0.4272(3) 0.0773(8) Uani 1 1 d . . . C6 C 0.4821(4) 1.04301(15) -0.3235(2) 0.0705(7) Uani 1 1 d . . . H6 H 0.3945 1.0127 -0.2903 0.085 Uiso 1 1 calc R . . C7 C 0.7316(4) 0.99411(15) -0.1623(2) 0.0680(7) Uani 1 1 d . . . H7 H 0.8593 0.9959 -0.1347 0.082 Uiso 1 1 calc R . . C8 C 0.6278(4) 0.94771(14) -0.1018(2) 0.0631(7) Uani 1 1 d . . . H8 H 0.4984 0.9463 -0.1233 0.076 Uiso 1 1 calc R . . C9 C 0.7141(4) 0.89869(14) -0.0018(2) 0.0591(6) Uani 1 1 d . . . C10 C 0.6238(3) 0.79947(13) 0.1453(2) 0.0546(6) Uani 1 1 d . . . C11 C 0.4706(3) 0.76349(15) 0.1825(2) 0.0683(7) Uani 1 1 d . . . H11 H 0.3509 0.7763 0.1460 0.082 Uiso 1 1 calc R . . C12 C 0.4908(3) 0.70841(16) 0.2735(2) 0.0708(7) Uani 1 1 d . . . H12 H 0.3853 0.6843 0.2973 0.085 Uiso 1 1 calc R . . C13 C 0.6664(3) 0.68928(14) 0.3285(2) 0.0606(6) Uani 1 1 d . . . C14 C 0.8195(4) 0.72490(16) 0.2901(3) 0.0737(8) Uani 1 1 d . . . H14 H 0.9392 0.7120 0.3264 0.088 Uiso 1 1 calc R . . C15 C 0.7994(3) 0.77917(15) 0.1993(2) 0.0684(7) Uani 1 1 d . . . H15 H 0.9053 0.8023 0.1741 0.082 Uiso 1 1 calc R . . C16 C 0.2248(5) 1.0866(2) -0.4857(3) 0.1028(11) Uani 1 1 d . . . H16A H 0.1643 1.1323 -0.4651 0.154 Uiso 1 1 calc R . . H16B H 0.1600 1.0444 -0.4551 0.154 Uiso 1 1 calc R . . H16C H 0.2221 1.0828 -0.5746 0.154 Uiso 1 1 calc R . . N1 N 0.5898(3) 0.85593(11) 0.05237(18) 0.0596(6) Uani 1 1 d . . . H1N H 0.4735 0.8641 0.0268 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 O2 0.0508(11) 0.0901(13) 0.0941(13) 0.0253(11) 0.0022(9) -0.0024(9) O1 0.0491(11) 0.0882(13) 0.0762(11) 0.0050(10) 0.0050(8) -0.0048(9) C1 0.0642(18) 0.0657(17) 0.0749(17) -0.0022(14) 0.0135(14) -0.0014(14) C2 0.079(2) 0.086(2) 0.107(2) 0.0144(19) 0.0154(18) -0.0083(17) C3 0.104(3) 0.106(3) 0.119(3) 0.037(2) 0.027(2) -0.008(2) C4 0.107(3) 0.090(2) 0.091(2) 0.0172(19) 0.018(2) 0.013(2) C5 0.083(2) 0.077(2) 0.0724(18) -0.0059(16) 0.0112(15) 0.0082(16) C6 0.0726(19) 0.0705(18) 0.0698(16) -0.0046(15) 0.0138(14) -0.0018(14) C7 0.0583(16) 0.0707(17) 0.0759(17) -0.0068(15) 0.0111(13) -0.0040(13) C8 0.0522(14) 0.0681(16) 0.0687(16) -0.0055(14) 0.0055(12) -0.0026(12) C9 0.0475(14) 0.0660(16) 0.0639(15) -0.0114(13) 0.0076(12) -0.0006(12) C10 0.0464(13) 0.0603(14) 0.0565(13) -0.0040(12) 0.0032(10) 0.0003(11) C11 0.0421(14) 0.0849(19) 0.0760(16) 0.0076(15) -0.0016(12) -0.0020(12) C12 0.0467(15) 0.0868(19) 0.0777(16) 0.0124(16) 0.0020(12) -0.0064(13) C13 0.0529(15) 0.0610(15) 0.0670(15) 0.0028(13) 0.0033(12) 0.0006(12) C14 0.0442(15) 0.0852(19) 0.0903(18) 0.0182(17) 0.0021(13) 0.0004(13) C15 0.0459(14) 0.0756(18) 0.0835(17) 0.0099(15) 0.0067(13) -0.0027(12) C16 0.097(3) 0.119(3) 0.088(2) -0.004(2) -0.0090(18) 0.018(2) N1 0.0430(11) 0.0684(13) 0.0669(12) 0.0003(11) 0.0050(9) 0.0000(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 O2 C13 1.375(3) . ? O2 H2O 0.8200 . ? O1 C9 1.237(3) . ? C1 C6 1.379(4) . ? C1 C2 1.389(4) . ? C1 C7 1.466(4) . ? C2 C3 1.388(4) . ? C2 H2 0.9300 . ? C3 C4 1.359(5) . ? C3 H3 0.9300 . ? C4 C5 1.379(4) . ? C4 H4 0.9300 . ? C5 C6 1.390(4) . ? C5 C16 1.489(4) . ? C6 H6 0.9300 . ? C7 C8 1.331(3) . ? C7 H7 0.9300 . ? C8 C9 1.468(3) . ? C8 H8 0.9300 . ? C9 N1 1.354(3) . ? C10 C11 1.370(3) . ? C10 C15 1.373(3) . ? C10 N1 1.421(3) . ? C11 C12 1.383(3) . ? C11 H11 0.9300 . ? C12 C13 1.371(3) . ? C12 H12 0.9300 . ? C13 C14 1.371(3) . ? C14 C15 1.372(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? N1 H1N 0.8600 . ? 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 C13 O2 H2O 109.5 . . ? C6 C1 C2 118.3(3) . . ? C6 C1 C7 123.2(2) . . ? C2 C1 C7 118.4(3) . . ? C3 C2 C1 120.1(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C4 C3 C2 119.7(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 122.4(3) . . ? C3 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C4 C5 C6 117.0(3) . . ? C4 C5 C16 121.3(3) . . ? C6 C5 C16 121.7(3) . . ? C1 C6 C5 122.5(3) . . ? C1 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? C8 C7 C1 126.7(3) . . ? C8 C7 H7 116.6 . . ? C1 C7 H7 116.6 . . ? C7 C8 C9 121.2(2) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? O1 C9 N1 122.2(2) . . ? O1 C9 C8 123.6(2) . . ? N1 C9 C8 114.2(2) . . ? C11 C10 C15 118.6(2) . . ? C11 C10 N1 117.3(2) . . ? C15 C10 N1 124.1(2) . . ? C10 C11 C12 121.1(2) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C13 C12 C11 120.0(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 118.7(2) . . ? C12 C13 O2 122.9(2) . . ? C14 C13 O2 118.4(2) . . ? C13 C14 C15 121.3(2) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C14 C15 C10 120.3(2) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? C5 C16 H16A 109.5 . . ? C5 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C5 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C9 N1 C10 129.4(2) . . ? C9 N1 H1N 115.3 . . ? C10 N1 H1N 115.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.1(4) . . . . ? C7 C1 C2 C3 177.6(3) . . . . ? C1 C2 C3 C4 -0.2(5) . . . . ? C2 C3 C4 C5 0.0(6) . . . . ? C3 C4 C5 C6 0.4(5) . . . . ? C3 C4 C5 C16 179.6(3) . . . . ? C2 C1 C6 C5 0.5(4) . . . . ? C7 C1 C6 C5 -177.0(2) . . . . ? C4 C5 C6 C1 -0.7(4) . . . . ? C16 C5 C6 C1 -179.9(3) . . . . ? C6 C1 C7 C8 -3.7(4) . . . . ? C2 C1 C7 C8 178.8(3) . . . . ? C1 C7 C8 C9 176.3(2) . . . . ? C7 C8 C9 O1 -2.1(4) . . . . ? C7 C8 C9 N1 178.7(2) . . . . ? C15 C10 C11 C12 0.7(4) . . . . ? N1 C10 C11 C12 -179.3(2) . . . . ? C10 C11 C12 C13 0.4(4) . . . . ? C11 C12 C13 C14 -1.0(4) . . . . ? C11 C12 C13 O2 178.9(2) . . . . ? C12 C13 C14 C15 0.5(4) . . . . ? O2 C13 C14 C15 -179.4(2) . . . . ? C13 C14 C15 C10 0.6(4) . . . . ? C11 C10 C15 C14 -1.2(4) . . . . ? N1 C10 C15 C14 178.8(2) . . . . ? O1 C9 N1 C10 -3.6(4) . . . . ? C8 C9 N1 C10 175.6(2) . . . . ? C11 C10 N1 C9 -178.9(2) . . . . ? C15 C10 N1 C9 1.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.205 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.042 data_3 _database_code_depnum_ccdc_archive 'CCDC 920707' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 N O2' _chemical_formula_sum 'C15 H13 N O2' _chemical_formula_weight 239.26 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.8140(3) _cell_length_b 18.4539(9) _cell_length_c 10.2513(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.1700(10) _cell_angle_gamma 90.00 _cell_volume 1283.80(11) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 9944 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 27.47 _exptl_crystal_description . _exptl_crystal_colour . _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7673 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details 'Absorption was corrected by ABSCOR' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Area Detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12450 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2925 _reflns_number_gt 2284 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+0.0844P] 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 2925 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1203 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.65560(19) -0.04098(6) -0.29139(12) 0.0569(3) Uani 1 1 d . . . C2 C 0.4575(2) -0.04714(7) -0.33876(13) 0.0644(3) Uani 1 1 d . . . H2 H 0.3628 -0.0209 -0.2990 0.077 Uiso 1 1 calc R . . C3 C 0.4002(3) -0.09146(9) -0.44343(15) 0.0791(4) Uani 1 1 d . . . H3 H 0.2676 -0.0948 -0.4737 0.095 Uiso 1 1 calc R . . C4 C 0.5373(3) -0.13071(10) -0.50323(18) 0.0913(5) Uani 1 1 d . . . H4 H 0.4977 -0.1608 -0.5735 0.110 Uiso 1 1 calc R . . C5 C 0.7329(3) -0.12564(10) -0.45939(19) 0.0976(6) Uani 1 1 d . . . H5 H 0.8260 -0.1520 -0.5005 0.117 Uiso 1 1 calc R . . C6 C 0.7922(2) -0.08128(9) -0.35366(16) 0.0773(4) Uani 1 1 d . . . H6 H 0.9251 -0.0785 -0.3241 0.093 Uiso 1 1 calc R . . C7 C 0.72273(17) 0.00511(6) -0.18038(12) 0.0541(3) Uani 1 1 d . . . H7 H 0.8564 0.0032 -0.1527 0.065 Uiso 1 1 calc R . . C8 C 0.61371(16) 0.04954(6) -0.11449(11) 0.0500(3) Uani 1 1 d . . . H8 H 0.4786 0.0517 -0.1374 0.060 Uiso 1 1 calc R . . C9 C 0.69996(15) 0.09528(6) -0.00653(11) 0.0462(3) Uani 1 1 d . . . C10 C 0.60513(14) 0.19427(6) 0.14102(11) 0.0450(3) Uani 1 1 d . . . C11 C 0.44374(15) 0.23508(7) 0.17175(12) 0.0561(3) Uani 1 1 d . . . H11 H 0.3192 0.2242 0.1318 0.067 Uiso 1 1 calc R . . C12 C 0.46533(16) 0.29131(7) 0.26027(13) 0.0592(3) Uani 1 1 d . . . H12 H 0.3558 0.3181 0.2793 0.071 Uiso 1 1 calc R . . C13 C 0.64960(16) 0.30818(6) 0.32113(12) 0.0516(3) Uani 1 1 d . . . C14 C 0.81034(15) 0.26748(7) 0.29115(13) 0.0576(3) Uani 1 1 d . . . H14 H 0.9345 0.2783 0.3316 0.069 Uiso 1 1 calc R . . C15 C 0.78978(15) 0.21119(7) 0.20251(12) 0.0542(3) Uani 1 1 d . . . H15 H 0.8996 0.1845 0.1838 0.065 Uiso 1 1 calc R . . N1 N 0.57012(12) 0.13859(5) 0.04749(9) 0.0475(2) Uani 1 1 d . . . H1 H 0.4483 0.1312 0.0211 0.057 Uiso 1 1 calc R . . O1 O 0.68148(11) 0.36415(5) 0.40827(10) 0.0672(3) Uani 1 1 d . . . H1A H 0.5761 0.3772 0.4333 0.101 Uiso 1 1 calc R . . O2 O 0.87863(11) 0.09506(5) 0.03042(9) 0.0602(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0659(7) 0.0515(6) 0.0542(7) 0.0065(5) 0.0111(5) 0.0059(5) C2 0.0679(8) 0.0672(8) 0.0586(7) 0.0004(6) 0.0092(6) -0.0025(6) C3 0.0906(11) 0.0809(10) 0.0651(9) -0.0014(7) 0.0028(7) -0.0122(8) C4 0.1193(15) 0.0815(11) 0.0728(10) -0.0167(8) 0.0080(10) -0.0040(10) C5 0.1192(15) 0.0875(12) 0.0890(12) -0.0221(10) 0.0258(11) 0.0232(10) C6 0.0795(9) 0.0748(9) 0.0786(10) -0.0089(7) 0.0119(7) 0.0177(7) C7 0.0514(6) 0.0546(6) 0.0567(7) 0.0067(5) 0.0066(5) 0.0051(5) C8 0.0447(6) 0.0521(6) 0.0531(6) 0.0070(5) 0.0042(5) 0.0018(4) C9 0.0405(5) 0.0501(6) 0.0480(6) 0.0113(4) 0.0050(4) 0.0022(4) C10 0.0382(5) 0.0486(5) 0.0480(6) 0.0070(4) 0.0023(4) 0.0000(4) C11 0.0333(5) 0.0680(7) 0.0654(7) -0.0078(6) -0.0034(5) 0.0013(5) C12 0.0361(5) 0.0709(7) 0.0698(8) -0.0129(6) 0.0001(5) 0.0078(5) C13 0.0400(5) 0.0570(6) 0.0572(7) -0.0013(5) 0.0009(5) -0.0012(4) C14 0.0349(5) 0.0675(7) 0.0687(8) -0.0064(6) -0.0043(5) -0.0003(5) C15 0.0356(5) 0.0604(7) 0.0657(7) -0.0017(6) 0.0003(5) 0.0054(4) N1 0.0347(4) 0.0525(5) 0.0547(5) 0.0015(4) 0.0011(4) 0.0005(4) O1 0.0391(4) 0.0776(6) 0.0838(6) -0.0261(5) -0.0013(4) 0.0007(4) O2 0.0405(4) 0.0770(6) 0.0626(5) -0.0017(4) 0.0015(3) 0.0092(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 C1 C6 1.3909(19) . ? C1 C2 1.3975(19) . ? C1 C7 1.4608(18) . ? C2 C3 1.377(2) . ? C2 H2 0.9300 . ? C3 C4 1.370(2) . ? C3 H3 0.9300 . ? C4 C5 1.371(3) . ? C4 H4 0.9300 . ? C5 C6 1.389(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.3307(16) . ? C7 H7 0.9300 . ? C8 C9 1.4715(16) . ? C8 H8 0.9300 . ? C9 O2 1.2420(12) . ? C9 N1 1.3478(14) . ? C10 C15 1.3911(15) . ? C10 C11 1.3922(15) . ? C10 N1 1.4109(14) . ? C11 C12 1.3776(17) . ? C11 H11 0.9300 . ? C12 C13 1.3862(15) . ? C12 H12 0.9300 . ? C13 O1 1.3701(14) . ? C13 C14 1.3853(16) . ? C14 C15 1.3789(17) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N1 H1 0.8600 . ? O1 H1A 0.8200 . ? 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 C6 C1 C2 117.56(13) . . ? C6 C1 C7 119.56(13) . . ? C2 C1 C7 122.88(11) . . ? C3 C2 C1 121.07(14) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C4 C3 C2 120.38(16) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.96(16) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.15(16) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 120.88(16) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? C8 C7 C1 127.18(11) . . ? C8 C7 H7 116.4 . . ? C1 C7 H7 116.4 . . ? C7 C8 C9 122.13(11) . . ? C7 C8 H8 118.9 . . ? C9 C8 H8 118.9 . . ? O2 C9 N1 122.57(10) . . ? O2 C9 C8 122.79(10) . . ? N1 C9 C8 114.62(9) . . ? C15 C10 C11 118.47(11) . . ? C15 C10 N1 124.20(10) . . ? C11 C10 N1 117.33(9) . . ? C12 C11 C10 121.12(10) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 120.28(11) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? O1 C13 C14 118.12(10) . . ? O1 C13 C12 123.15(10) . . ? C14 C13 C12 118.73(11) . . ? C15 C14 C13 121.28(10) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C10 120.12(10) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? C9 N1 C10 129.34(9) . . ? C9 N1 H1 115.3 . . ? C10 N1 H1 115.3 . . ? C13 O1 H1A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.1(2) . . . . ? C7 C1 C2 C3 -179.73(12) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C4 C5 C6 C1 -0.5(3) . . . . ? C2 C1 C6 C5 0.3(2) . . . . ? C7 C1 C6 C5 179.94(14) . . . . ? C6 C1 C7 C8 176.41(13) . . . . ? C2 C1 C7 C8 -3.96(19) . . . . ? C1 C7 C8 C9 -177.91(10) . . . . ? C7 C8 C9 O2 -0.48(17) . . . . ? C7 C8 C9 N1 178.26(10) . . . . ? C15 C10 C11 C12 0.42(18) . . . . ? N1 C10 C11 C12 -178.82(11) . . . . ? C10 C11 C12 C13 -0.2(2) . . . . ? C11 C12 C13 O1 178.85(12) . . . . ? C11 C12 C13 C14 0.0(2) . . . . ? O1 C13 C14 C15 -178.81(11) . . . . ? C12 C13 C14 C15 0.1(2) . . . . ? C13 C14 C15 C10 0.06(19) . . . . ? C11 C10 C15 C14 -0.32(18) . . . . ? N1 C10 C15 C14 178.86(11) . . . . ? O2 C9 N1 C10 6.70(17) . . . . ? C8 C9 N1 C10 -172.04(10) . . . . ? C15 C10 N1 C9 -4.69(18) . . . . ? C11 C10 N1 C9 174.50(11) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.138 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.036 data_4 _database_code_depnum_ccdc_archive 'CCDC 920708' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H15 N O2' _chemical_formula_sum 'C16 H15 N O2' _chemical_formula_weight 253.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 20.0583(4) _cell_length_b 7.16980(10) _cell_length_c 20.3740(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.1500(10) _cell_angle_gamma 90.00 _cell_volume 2694.13(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20849 _cell_measurement_theta_min 3.57 _cell_measurement_theta_max 68.17 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.662 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7397 _exptl_absorpt_correction_T_max 0.9740 _exptl_absorpt_process_details 'Absorption was corrected by ABSCOR' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID II IP Area Detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29886 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.72 _diffrn_reflns_theta_max 68.18 _reflns_number_total 4892 _reflns_number_gt 2956 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0864P)^2^+0.2554P] 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 4892 _refine_ls_number_parameters 345 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0858 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1765 _refine_ls_wR_factor_gt 0.1305 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.41443(13) -0.0011(3) 0.37560(12) 0.0533(6) Uani 1 1 d . . . C2 C 0.45933(14) -0.1535(4) 0.40852(13) 0.0579(6) Uani 1 1 d . . . C3 C 0.53384(15) -0.1283(5) 0.43458(15) 0.0755(8) Uani 1 1 d . . . H3 H 0.5642 -0.2278 0.4565 0.091 Uiso 1 1 calc R . . C4 C 0.56403(17) 0.0397(5) 0.42889(16) 0.0837(9) Uani 1 1 d . . . H4 H 0.6142 0.0532 0.4473 0.100 Uiso 1 1 calc R . . C5 C 0.52019(17) 0.1880(5) 0.39605(16) 0.0796(9) Uani 1 1 d . . . H5 H 0.5405 0.3013 0.3914 0.096 Uiso 1 1 calc R . . C6 C 0.44607(15) 0.1679(4) 0.37013(14) 0.0653(7) Uani 1 1 d . . . H6 H 0.4166 0.2691 0.3486 0.078 Uiso 1 1 calc R . . C7 C 0.33589(13) -0.0219(3) 0.34789(12) 0.0528(6) Uani 1 1 d . . . H7 H 0.3189 -0.1439 0.3432 0.063 Uiso 1 1 calc R . . C8 C 0.28543(13) 0.1095(3) 0.32849(12) 0.0521(6) Uani 1 1 d . . . H8 H 0.2992 0.2341 0.3310 0.062 Uiso 1 1 calc R . . C9 C 0.20788(13) 0.0618(3) 0.30306(12) 0.0484(6) Uani 1 1 d . . . C10 C 0.08667(13) 0.2056(3) 0.27747(12) 0.0483(6) Uani 1 1 d . . . C11 C 0.05165(13) 0.3766(3) 0.26699(12) 0.0526(6) Uani 1 1 d . . . H11 H 0.0784 0.4858 0.2729 0.063 Uiso 1 1 calc R . . C12 C -0.02240(13) 0.3870(3) 0.24792(12) 0.0526(6) Uani 1 1 d . . . H12 H -0.0451 0.5026 0.2413 0.063 Uiso 1 1 calc R . . C13 C -0.06249(13) 0.2260(3) 0.23876(12) 0.0517(6) Uani 1 1 d . . . C14 C -0.02775(14) 0.0564(4) 0.25005(16) 0.0712(8) Uani 1 1 d . . . H14 H -0.0545 -0.0526 0.2449 0.085 Uiso 1 1 calc R . . C15 C 0.04634(14) 0.0456(3) 0.26898(15) 0.0683(8) Uani 1 1 d . . . H15 H 0.0689 -0.0702 0.2760 0.082 Uiso 1 1 calc R . . C16 C 0.42881(16) -0.3407(4) 0.41531(16) 0.0768(8) Uani 1 1 d . . . H16A H 0.4678 -0.4275 0.4370 0.115 Uiso 1 1 calc R . . H16B H 0.3978 -0.3850 0.3688 0.115 Uiso 1 1 calc R . . H16C H 0.4013 -0.3291 0.4445 0.115 Uiso 1 1 calc R . . O1 O 0.18515(8) -0.1006(2) 0.28881(9) 0.0591(5) Uani 1 1 d . . . O2 O -0.13667(9) 0.2261(2) 0.21910(9) 0.0647(5) Uani 1 1 d . . . H2 H -0.1516 0.3338 0.2137 0.097 Uiso 1 1 calc R . . C17 C 0.63578(13) 0.1426(3) 0.10555(13) 0.0539(6) Uani 1 1 d . . . C18 C 0.60734(13) -0.0124(4) 0.06144(13) 0.0587(6) Uani 1 1 d . . . C19 C 0.58546(14) 0.0104(5) -0.01210(15) 0.0716(8) Uani 1 1 d . . . H19 H 0.5666 -0.0912 -0.0420 0.086 Uiso 1 1 calc R . . C20 C 0.59108(16) 0.1789(5) -0.04135(16) 0.0805(9) Uani 1 1 d . . . H20 H 0.5759 0.1905 -0.0906 0.097 Uiso 1 1 calc R . . C21 C 0.61904(17) 0.3300(5) 0.00176(16) 0.0819(9) Uani 1 1 d . . . H21 H 0.6228 0.4444 -0.0180 0.098 Uiso 1 1 calc R . . C22 C 0.64149(15) 0.3114(4) 0.07449(14) 0.0698(8) Uani 1 1 d . . . H22 H 0.6609 0.4141 0.1036 0.084 Uiso 1 1 calc R . . C23 C 0.65866(12) 0.1252(3) 0.18262(13) 0.0554(6) Uani 1 1 d . . . H23 H 0.6634 0.0039 0.2001 0.066 Uiso 1 1 calc R . . C24 C 0.67364(13) 0.2591(3) 0.23108(12) 0.0549(6) Uani 1 1 d . . . H24 H 0.6715 0.3827 0.2167 0.066 Uiso 1 1 calc R . . C25 C 0.69352(12) 0.2173(3) 0.30716(12) 0.0511(6) Uani 1 1 d . . . C26 C 0.71984(12) 0.3717(3) 0.42445(12) 0.0484(6) Uani 1 1 d . . . C27 C 0.70839(14) 0.5377(3) 0.45327(13) 0.0596(7) Uani 1 1 d . . . H27 H 0.6891 0.6395 0.4236 0.071 Uiso 1 1 calc R . . C28 C 0.72527(15) 0.5535(3) 0.52535(13) 0.0624(7) Uani 1 1 d . . . H28 H 0.7172 0.6658 0.5439 0.075 Uiso 1 1 calc R . . C29 C 0.75404(13) 0.4046(3) 0.57038(12) 0.0509(6) Uani 1 1 d . . . C30 C 0.76570(13) 0.2394(3) 0.54193(12) 0.0535(6) Uani 1 1 d . . . H30 H 0.7852 0.1381 0.5719 0.064 Uiso 1 1 calc R . . C31 C 0.74877(13) 0.2221(3) 0.46945(12) 0.0542(6) Uani 1 1 d . . . H31 H 0.7569 0.1097 0.4510 0.065 Uiso 1 1 calc R . . C32 C 0.59971(16) -0.1999(4) 0.09044(15) 0.0774(8) Uani 1 1 d . . . H32A H 0.5751 -0.2834 0.0516 0.116 Uiso 1 1 calc R . . H32B H 0.5722 -0.1875 0.1196 0.116 Uiso 1 1 calc R . . H32C H 0.6469 -0.2486 0.1187 0.116 Uiso 1 1 calc R . . N1 N 0.16289(10) 0.2078(3) 0.29689(10) 0.0525(5) Uani 1 1 d . . . H1 H 0.1831 0.3159 0.3059 0.063 Uiso 1 1 calc R . . N17 N 0.70307(10) 0.3673(3) 0.34995(10) 0.0529(5) Uani 1 1 d . . . H17 H 0.6984 0.4741 0.3294 0.064 Uiso 1 1 calc R . . O17 O 0.70011(9) 0.0554(2) 0.33033(9) 0.0639(5) Uani 1 1 d . . . O18 O 0.76983(9) 0.4272(2) 0.64197(8) 0.0612(5) Uani 1 1 d . . . H18 H 0.7866 0.3298 0.6631 0.092 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0601(15) 0.0453(14) 0.0545(14) -0.0041(11) 0.0227(11) 0.0004(12) C2 0.0635(16) 0.0546(16) 0.0544(15) 0.0003(12) 0.0218(12) 0.0061(13) C3 0.0608(17) 0.087(2) 0.0734(19) 0.0003(16) 0.0206(14) 0.0101(16) C4 0.0603(18) 0.103(3) 0.084(2) -0.0108(19) 0.0247(16) -0.0111(18) C5 0.077(2) 0.077(2) 0.088(2) -0.0125(17) 0.0364(17) -0.0194(17) C6 0.0698(18) 0.0533(17) 0.0751(18) -0.0078(13) 0.0308(14) -0.0070(13) C7 0.0587(14) 0.0416(14) 0.0565(14) 0.0006(11) 0.0209(11) 0.0001(11) C8 0.0609(15) 0.0402(14) 0.0560(14) 0.0012(11) 0.0239(11) -0.0018(11) C9 0.0604(15) 0.0385(14) 0.0450(13) 0.0013(10) 0.0192(11) 0.0049(11) C10 0.0554(14) 0.0380(13) 0.0495(13) 0.0008(10) 0.0184(10) 0.0033(11) C11 0.0639(15) 0.0377(14) 0.0556(14) 0.0022(11) 0.0227(11) -0.0011(11) C12 0.0599(15) 0.0366(14) 0.0589(15) 0.0013(11) 0.0209(12) 0.0039(11) C13 0.0524(14) 0.0456(14) 0.0560(14) -0.0053(11) 0.0200(11) 0.0007(11) C14 0.0594(16) 0.0369(15) 0.113(2) -0.0055(14) 0.0298(15) 0.0000(12) C15 0.0625(17) 0.0352(15) 0.103(2) -0.0019(14) 0.0280(15) 0.0022(12) C16 0.086(2) 0.0535(18) 0.083(2) 0.0100(15) 0.0250(16) 0.0140(15) O1 0.0635(10) 0.0368(10) 0.0689(11) -0.0061(8) 0.0173(8) -0.0011(8) O2 0.0564(10) 0.0456(10) 0.0844(13) -0.0069(9) 0.0195(9) 0.0017(8) C17 0.0587(15) 0.0500(15) 0.0526(14) -0.0055(12) 0.0216(11) -0.0009(12) C18 0.0584(15) 0.0567(16) 0.0598(16) -0.0091(13) 0.0219(12) 0.0011(12) C19 0.0694(18) 0.080(2) 0.0636(18) -0.0175(16) 0.0239(14) -0.0039(15) C20 0.084(2) 0.102(3) 0.0532(17) -0.0051(17) 0.0247(15) -0.0096(18) C21 0.101(2) 0.081(2) 0.0624(19) 0.0040(16) 0.0308(16) -0.0111(18) C22 0.090(2) 0.0588(18) 0.0579(17) -0.0019(13) 0.0257(14) -0.0088(15) C23 0.0627(15) 0.0470(15) 0.0547(15) -0.0002(11) 0.0213(12) 0.0039(12) C24 0.0634(16) 0.0465(15) 0.0511(14) 0.0012(11) 0.0184(11) 0.0007(11) C25 0.0506(13) 0.0442(15) 0.0533(14) -0.0032(11) 0.0147(10) -0.0027(11) C26 0.0519(13) 0.0437(14) 0.0471(13) -0.0030(10) 0.0168(10) -0.0036(11) C27 0.0769(17) 0.0421(15) 0.0554(15) 0.0019(11) 0.0214(12) 0.0048(12) C28 0.0873(19) 0.0392(15) 0.0576(16) -0.0035(12) 0.0252(13) 0.0046(13) C29 0.0615(14) 0.0412(14) 0.0492(14) -0.0040(11) 0.0210(11) -0.0073(11) C30 0.0650(15) 0.0403(14) 0.0535(14) 0.0022(11) 0.0215(11) 0.0003(11) C31 0.0659(15) 0.0431(14) 0.0535(15) 0.0007(11) 0.0235(12) 0.0050(11) C32 0.084(2) 0.0542(18) 0.085(2) -0.0137(15) 0.0244(16) -0.0058(15) N1 0.0562(12) 0.0351(11) 0.0632(13) -0.0009(9) 0.0201(9) -0.0009(9) N17 0.0646(12) 0.0407(11) 0.0500(12) -0.0012(9) 0.0188(9) -0.0017(9) O17 0.0806(12) 0.0412(10) 0.0592(11) -0.0001(8) 0.0161(9) -0.0012(8) O18 0.0857(12) 0.0433(10) 0.0507(10) -0.0036(7) 0.0227(9) -0.0033(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.393(3) . ? C1 C2 1.407(3) . ? C1 C7 1.457(3) . ? C2 C3 1.387(3) . ? C2 C16 1.504(4) . ? C3 C4 1.373(4) . ? C3 H3 0.9300 . ? C4 C5 1.374(4) . ? C4 H4 0.9300 . ? C5 C6 1.376(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.324(3) . ? C7 H7 0.9300 . ? C8 C9 1.474(3) . ? C8 H8 0.9300 . ? C9 O1 1.243(3) . ? C9 N1 1.355(3) . ? C10 C15 1.375(3) . ? C10 C11 1.387(3) . ? C10 N1 1.421(3) . ? C11 C12 1.382(3) . ? C11 H11 0.9300 . ? C12 C13 1.377(3) . ? C12 H12 0.9300 . ? C13 C14 1.375(3) . ? C13 O2 1.381(3) . ? C14 C15 1.383(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? O2 H2 0.8200 . ? C17 C22 1.391(3) . ? C17 C18 1.402(3) . ? C17 C23 1.458(3) . ? C18 C19 1.395(4) . ? C18 C32 1.500(3) . ? C19 C20 1.371(4) . ? C19 H19 0.9300 . ? C20 C21 1.368(4) . ? C20 H20 0.9300 . ? C21 C22 1.375(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.324(3) . ? C23 H23 0.9300 . ? C24 C25 1.472(3) . ? C24 H24 0.9300 . ? C25 O17 1.240(3) . ? C25 N17 1.350(3) . ? C26 C31 1.382(3) . ? C26 C27 1.386(3) . ? C26 N17 1.420(3) . ? C27 C28 1.376(3) . ? C27 H27 0.9300 . ? C28 C29 1.378(3) . ? C28 H28 0.9300 . ? C29 O18 1.375(3) . ? C29 C30 1.378(3) . ? C30 C31 1.385(3) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? N1 H1 0.8600 . ? N17 H17 0.8600 . ? O18 H18 0.8200 . ? 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 C6 C1 C2 119.2(2) . . ? C6 C1 C7 121.0(2) . . ? C2 C1 C7 119.8(2) . . ? C3 C2 C1 118.2(3) . . ? C3 C2 C16 119.8(3) . . ? C1 C2 C16 122.0(2) . . ? C4 C3 C2 121.8(3) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 119.6(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 121.2(3) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? C8 C7 C1 128.7(2) . . ? C8 C7 H7 115.6 . . ? C1 C7 H7 115.6 . . ? C7 C8 C9 121.1(2) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? O1 C9 N1 122.2(2) . . ? O1 C9 C8 122.6(2) . . ? N1 C9 C8 115.2(2) . . ? C15 C10 C11 118.7(2) . . ? C15 C10 N1 124.0(2) . . ? C11 C10 N1 117.2(2) . . ? C12 C11 C10 120.9(2) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C13 C12 C11 119.9(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 119.2(2) . . ? C14 C13 O2 117.8(2) . . ? C12 C13 O2 123.0(2) . . ? C13 C14 C15 121.0(2) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C10 C15 C14 120.2(2) . . ? C10 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C2 C16 H16A 109.5 . . ? C2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 O2 H2 109.5 . . ? C22 C17 C18 118.9(2) . . ? C22 C17 C23 121.1(2) . . ? C18 C17 C23 119.9(2) . . ? C19 C18 C17 118.2(3) . . ? C19 C18 C32 119.4(2) . . ? C17 C18 C32 122.5(2) . . ? C20 C19 C18 121.7(3) . . ? C20 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C21 C20 C19 120.1(3) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 119.5(3) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C21 C22 C17 121.6(3) . . ? C21 C22 H22 119.2 . . ? C17 C22 H22 119.2 . . ? C24 C23 C17 128.6(2) . . ? C24 C23 H23 115.7 . . ? C17 C23 H23 115.7 . . ? C23 C24 C25 121.7(2) . . ? C23 C24 H24 119.1 . . ? C25 C24 H24 119.1 . . ? O17 C25 N17 122.2(2) . . ? O17 C25 C24 122.4(2) . . ? N17 C25 C24 115.4(2) . . ? C31 C26 C27 118.8(2) . . ? C31 C26 N17 123.6(2) . . ? C27 C26 N17 117.6(2) . . ? C28 C27 C26 120.7(2) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C27 C28 C29 120.6(2) . . ? C27 C28 H28 119.7 . . ? C29 C28 H28 119.7 . . ? O18 C29 C28 118.5(2) . . ? O18 C29 C30 122.7(2) . . ? C28 C29 C30 118.8(2) . . ? C29 C30 C31 121.0(2) . . ? C29 C30 H30 119.5 . . ? C31 C30 H30 119.5 . . ? C26 C31 C30 120.1(2) . . ? C26 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C18 C32 H32A 109.5 . . ? C18 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C18 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C9 N1 C10 128.4(2) . . ? C9 N1 H1 115.8 . . ? C10 N1 H1 115.8 . . ? C25 N17 C26 128.4(2) . . ? C25 N17 H17 115.8 . . ? C26 N17 H17 115.8 . . ? C29 O18 H18 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.3(3) . . . . ? C7 C1 C2 C3 -179.7(2) . . . . ? C6 C1 C2 C16 -179.1(2) . . . . ? C7 C1 C2 C16 0.9(4) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? C16 C2 C3 C4 179.4(3) . . . . ? C2 C3 C4 C5 -0.7(5) . . . . ? C3 C4 C5 C6 1.2(5) . . . . ? C4 C5 C6 C1 -0.9(4) . . . . ? C2 C1 C6 C5 0.2(4) . . . . ? C7 C1 C6 C5 -179.8(2) . . . . ? C6 C1 C7 C8 -14.7(4) . . . . ? C2 C1 C7 C8 165.3(2) . . . . ? C1 C7 C8 C9 -178.5(2) . . . . ? C7 C8 C9 O1 -10.5(3) . . . . ? C7 C8 C9 N1 168.9(2) . . . . ? C15 C10 C11 C12 -0.4(4) . . . . ? N1 C10 C11 C12 179.92(19) . . . . ? C10 C11 C12 C13 -0.3(4) . . . . ? C11 C12 C13 C14 1.2(4) . . . . ? C11 C12 C13 O2 -179.4(2) . . . . ? C12 C13 C14 C15 -1.3(4) . . . . ? O2 C13 C14 C15 179.2(2) . . . . ? C11 C10 C15 C14 0.3(4) . . . . ? N1 C10 C15 C14 179.9(2) . . . . ? C13 C14 C15 C10 0.6(4) . . . . ? C22 C17 C18 C19 -0.4(4) . . . . ? C23 C17 C18 C19 179.4(2) . . . . ? C22 C17 C18 C32 179.6(2) . . . . ? C23 C17 C18 C32 -0.5(4) . . . . ? C17 C18 C19 C20 -0.2(4) . . . . ? C32 C18 C19 C20 179.8(3) . . . . ? C18 C19 C20 C21 0.3(4) . . . . ? C19 C20 C21 C22 0.1(5) . . . . ? C20 C21 C22 C17 -0.7(4) . . . . ? C18 C17 C22 C21 0.9(4) . . . . ? C23 C17 C22 C21 -179.0(2) . . . . ? C22 C17 C23 C24 13.8(4) . . . . ? C18 C17 C23 C24 -166.1(2) . . . . ? C17 C23 C24 C25 177.6(2) . . . . ? C23 C24 C25 O17 2.9(4) . . . . ? C23 C24 C25 N17 -176.1(2) . . . . ? C31 C26 C27 C28 -0.2(4) . . . . ? N17 C26 C27 C28 -178.2(2) . . . . ? C26 C27 C28 C29 0.1(4) . . . . ? C27 C28 C29 O18 -179.8(2) . . . . ? C27 C28 C29 C30 0.1(4) . . . . ? O18 C29 C30 C31 179.7(2) . . . . ? C28 C29 C30 C31 -0.2(4) . . . . ? C27 C26 C31 C30 0.1(4) . . . . ? N17 C26 C31 C30 178.0(2) . . . . ? C29 C30 C31 C26 0.1(4) . . . . ? O1 C9 N1 C10 2.9(4) . . . . ? C8 C9 N1 C10 -176.5(2) . . . . ? C15 C10 N1 C9 7.6(4) . . . . ? C11 C10 N1 C9 -172.8(2) . . . . ? O17 C25 N17 C26 -1.4(4) . . . . ? C24 C25 N17 C26 177.7(2) . . . . ? C31 C26 N17 C25 18.7(4) . . . . ? C27 C26 N17 C25 -163.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 68.18 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.267 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.058 data_6 _database_code_depnum_ccdc_archive 'CCDC 920709' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C16 H15 N O2)' _chemical_formula_sum 'C32 H30 N2 O4' _chemical_formula_weight 506.58 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.8016(6) _cell_length_b 12.5421(10) _cell_length_c 16.2644(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.012(2) _cell_angle_gamma 90.00 _cell_volume 1385.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7139 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.33 _exptl_crystal_description . _exptl_crystal_colour . _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4775 _exptl_absorpt_correction_T_max 0.9896 _exptl_absorpt_process_details 'Absorption was corrected by ABSCOR' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Area Detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13035 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.42 _reflns_number_total 3147 _reflns_number_gt 1505 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0614P)^2^+0.1719P] 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 3147 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1183 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1577 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2954(7) 0.0106(2) -0.0911(3) 0.189(2) Uani 1 1 d . . . H1A H 0.2908 0.0024 -0.1499 0.283 Uiso 1 1 calc R . . H1B H 0.1976 -0.0343 -0.0684 0.283 Uiso 1 1 calc R . . H1C H 0.4235 -0.0094 -0.0686 0.283 Uiso 1 1 calc R . . C2 C 0.2547(6) 0.1267(2) -0.06964(18) 0.1061(11) Uani 1 1 d . . . C3 C 0.3994(5) 0.1937(2) -0.03876(17) 0.0993(9) Uani 1 1 d . . . H3 H 0.5269 0.1678 -0.0302 0.119 Uiso 1 1 calc R . . C4 C 0.3612(4) 0.29857(19) -0.02006(15) 0.0760(7) Uani 1 1 d . . . H4 H 0.4630 0.3418 0.0008 0.091 Uiso 1 1 calc R . . C5 C 0.1737(3) 0.34062(16) -0.03188(13) 0.0627(6) Uani 1 1 d . . . C6 C 0.0259(4) 0.27338(17) -0.06280(16) 0.0810(7) Uani 1 1 d . . . H6 H -0.1018 0.2991 -0.0712 0.097 Uiso 1 1 calc R . . C7 C 0.0671(5) 0.1680(2) -0.08126(18) 0.1008(9) Uani 1 1 d . . . H7 H -0.0341 0.1241 -0.1019 0.121 Uiso 1 1 calc R . . C8 C 0.1370(3) 0.45531(15) -0.01142(13) 0.0596(5) Uani 1 1 d . . . H8 H 0.2623 0.4940 -0.0074 0.072 Uiso 1 1 calc R . . C9 C 0.0468(3) 0.03784(17) 0.27730(13) 0.0662(6) Uani 1 1 d . . . C10 C -0.1084(3) 0.10720(17) 0.27930(13) 0.0668(6) Uani 1 1 d . . . H10 H -0.2187 0.0887 0.3076 0.080 Uiso 1 1 calc R . . C11 C -0.1025(3) 0.20494(17) 0.23939(14) 0.0678(6) Uani 1 1 d . . . H11 H -0.2083 0.2517 0.2414 0.081 Uiso 1 1 calc R . . C12 C 0.0591(3) 0.23277(16) 0.19691(12) 0.0580(5) Uani 1 1 d . . . C13 C 0.2145(3) 0.16240(19) 0.19458(15) 0.0775(7) Uani 1 1 d . . . H13 H 0.3244 0.1804 0.1658 0.093 Uiso 1 1 calc R . . C14 C 0.2082(3) 0.0656(2) 0.23453(16) 0.0840(8) Uani 1 1 d . . . H14 H 0.3138 0.0187 0.2325 0.101 Uiso 1 1 calc R . . C15 C -0.0619(3) 0.38843(15) 0.11312(13) 0.0578(5) Uani 1 1 d . . . C16 C 0.0153(3) 0.48118(15) 0.06613(13) 0.0585(5) Uani 1 1 d . . . H16 H 0.0898 0.5295 0.1035 0.070 Uiso 1 1 calc R . . N1 N 0.0775(2) 0.33209(13) 0.15545(11) 0.0644(5) Uani 1 1 d . . . H1 H 0.1934 0.3596 0.1579 0.077 Uiso 1 1 calc R . . O1 O 0.0493(2) -0.05963(14) 0.31631(12) 0.0939(6) Uani 1 1 d . . . H1O H -0.0541 -0.0680 0.3393 0.141 Uiso 1 1 calc R . . O2 O -0.2380(2) 0.36447(11) 0.11181(10) 0.0716(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.276(5) 0.096(2) 0.183(4) -0.064(2) -0.100(4) 0.091(3) C2 0.159(3) 0.0718(17) 0.0840(19) -0.0166(14) -0.0286(19) 0.0446(19) C3 0.119(2) 0.092(2) 0.0853(19) -0.0099(15) -0.0159(17) 0.0476(18) C4 0.0797(15) 0.0756(16) 0.0719(15) 0.0005(12) -0.0035(12) 0.0196(12) C5 0.0686(13) 0.0574(13) 0.0628(13) -0.0001(10) 0.0091(11) 0.0054(11) C6 0.0843(16) 0.0605(14) 0.0978(19) -0.0114(13) 0.0008(14) 0.0044(12) C7 0.135(3) 0.0607(15) 0.104(2) -0.0178(14) -0.0194(19) 0.0084(16) C8 0.0517(11) 0.0532(11) 0.0741(14) -0.0026(10) 0.0038(10) -0.0003(9) C9 0.0556(12) 0.0750(14) 0.0680(14) 0.0186(11) 0.0042(10) 0.0057(11) C10 0.0604(12) 0.0744(15) 0.0668(14) 0.0049(11) 0.0154(10) 0.0035(11) C11 0.0652(13) 0.0666(14) 0.0729(14) -0.0013(11) 0.0145(11) 0.0107(11) C12 0.0563(12) 0.0615(12) 0.0561(12) 0.0043(10) 0.0023(9) 0.0006(10) C13 0.0555(13) 0.0943(17) 0.0843(17) 0.0294(13) 0.0167(11) 0.0130(12) C14 0.0579(14) 0.0978(18) 0.0979(19) 0.0374(15) 0.0173(13) 0.0216(12) C15 0.0571(12) 0.0536(12) 0.0625(13) -0.0095(9) 0.0021(10) -0.0007(10) C16 0.0578(11) 0.0494(11) 0.0678(13) -0.0074(9) -0.0001(10) -0.0017(9) N1 0.0564(10) 0.0641(11) 0.0724(12) 0.0051(9) -0.0011(9) -0.0046(8) O1 0.0648(10) 0.0988(12) 0.1197(14) 0.0521(11) 0.0189(9) 0.0159(8) O2 0.0550(9) 0.0685(9) 0.0915(11) 0.0048(8) 0.0054(7) -0.0004(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.526(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.370(4) . ? C2 C7 1.381(4) . ? C3 C4 1.378(3) . ? C3 H3 0.9300 . ? C4 C5 1.384(3) . ? C4 H4 0.9300 . ? C5 C6 1.386(3) . ? C5 C8 1.500(3) . ? C6 C7 1.387(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C16 1.550(3) 3_565 ? C8 C16 1.578(3) . ? C8 H8 0.9800 . ? C9 C10 1.370(3) . ? C9 C14 1.375(3) . ? C9 O1 1.377(2) . ? C10 C11 1.389(3) . ? C10 H10 0.9300 . ? C11 C12 1.374(3) . ? C11 H11 0.9300 . ? C12 C13 1.379(3) . ? C12 N1 1.425(2) . ? C13 C14 1.379(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 O2 1.234(2) . ? C15 N1 1.343(2) . ? C15 C16 1.502(3) . ? C16 C8 1.550(3) 3_565 ? C16 H16 0.9800 . ? N1 H1 0.8600 . ? O1 H1O 0.8200 . ? 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C7 117.4(2) . . ? C3 C2 C1 122.3(3) . . ? C7 C2 C1 120.3(3) . . ? C2 C3 C4 121.8(3) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C3 C4 C5 121.1(2) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 117.6(2) . . ? C4 C5 C8 119.8(2) . . ? C6 C5 C8 122.53(19) . . ? C5 C6 C7 120.5(2) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C2 C7 C6 121.6(3) . . ? C2 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C5 C8 C16 118.64(18) . 3_565 ? C5 C8 C16 118.34(17) . . ? C16 C8 C16 89.45(15) 3_565 . ? C5 C8 H8 109.6 . . ? C16 C8 H8 109.6 3_565 . ? C16 C8 H8 109.6 . . ? C10 C9 C14 119.2(2) . . ? C10 C9 O1 122.93(19) . . ? C14 C9 O1 117.84(19) . . ? C9 C10 C11 120.5(2) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 120.20(19) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 119.07(19) . . ? C11 C12 N1 123.55(19) . . ? C13 C12 N1 117.37(18) . . ? C14 C13 C12 120.5(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C9 C14 C13 120.4(2) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? O2 C15 N1 122.63(19) . . ? O2 C15 C16 123.01(19) . . ? N1 C15 C16 114.34(18) . . ? C15 C16 C8 116.70(17) . 3_565 ? C15 C16 C8 117.35(15) . . ? C8 C16 C8 90.55(15) 3_565 . ? C15 C16 H16 110.3 . . ? C8 C16 H16 110.3 3_565 . ? C8 C16 H16 110.3 . . ? C15 N1 C12 128.69(17) . . ? C15 N1 H1 115.7 . . ? C12 N1 H1 115.7 . . ? C9 O1 H1O 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 C2 C3 C4 -0.2(5) . . . . ? C1 C2 C3 C4 179.6(3) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C3 C4 C5 C8 -179.6(2) . . . . ? C4 C5 C6 C7 -0.3(4) . . . . ? C8 C5 C6 C7 179.6(2) . . . . ? C3 C2 C7 C6 0.2(5) . . . . ? C1 C2 C7 C6 -179.6(3) . . . . ? C5 C6 C7 C2 0.0(4) . . . . ? C4 C5 C8 C16 144.6(2) . . . 3_565 ? C6 C5 C8 C16 -35.4(3) . . . 3_565 ? C4 C5 C8 C16 -109.1(2) . . . . ? C6 C5 C8 C16 71.0(3) . . . . ? C14 C9 C10 C11 -0.7(4) . . . . ? O1 C9 C10 C11 179.5(2) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? C10 C11 C12 C13 0.0(3) . . . . ? C10 C11 C12 N1 -179.0(2) . . . . ? C11 C12 C13 C14 -0.2(4) . . . . ? N1 C12 C13 C14 178.9(2) . . . . ? C10 C9 C14 C13 0.5(4) . . . . ? O1 C9 C14 C13 -179.7(2) . . . . ? C12 C13 C14 C9 0.0(4) . . . . ? O2 C15 C16 C8 -2.6(3) . . . 3_565 ? N1 C15 C16 C8 176.03(16) . . . 3_565 ? O2 C15 C16 C8 -108.4(2) . . . . ? N1 C15 C16 C8 70.2(2) . . . . ? C5 C8 C16 C15 -1.9(3) . . . . ? C16 C8 C16 C15 120.7(2) 3_565 . . . ? C5 C8 C16 C8 -122.6(2) . . . 3_565 ? C16 C8 C16 C8 0.0 3_565 . . 3_565 ? O2 C15 N1 C12 7.8(3) . . . . ? C16 C15 N1 C12 -170.83(18) . . . . ? C11 C12 N1 C15 -37.5(3) . . . . ? C13 C12 N1 C15 143.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.213 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.041