# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Lin, Wenwei' _publ_contact_author_email wenweilin@ntnu.edu.tw _publ_section_title ; Organocatalytic Tandem Three-Component Reaction of Aldehyde, Alkyl Vinylketone, and Amide: One-Pot Syntheses of Highly Functional Alkenes ; loop_ _publ_author_name D.-W.Wang S.-e.Syu Y.-T.Hung P.-y.Chen C.-J.Lee K.-W.Chen ; Yu.Chen ; W.Lin data_10628 _database_code_depnum_ccdc_archive 'CCDC 769605' #TrackingRef '10628.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 F3 N1 O3' _chemical_formula_sum 'C20 H14 F3 N O3' _chemical_formula_weight 373.32 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' F F 0.0171 0.0103 '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 'P 21/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 8.7790(2) _cell_length_b 15.4270(4) _cell_length_c 12.6700(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.858(2) _cell_angle_gamma 90.00 _cell_volume 1709.78(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6851 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9293 _exptl_absorpt_correction_T_max 1.0165 _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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11613 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3027 _reflns_number_gt 2012 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.2000P)^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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3027 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.2306 _refine_ls_wR_factor_gt 0.1862 _refine_ls_goodness_of_fit_ref 0.863 _refine_ls_restrained_S_all 0.863 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.004 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 F1 F -0.2853(4) 0.35206(19) 0.1044(2) 0.1446(14) Uani 1 1 d . . . F2 F -0.3321(3) 0.40346(16) -0.0469(2) 0.1050(9) Uani 1 1 d . . . F3 F -0.1308(3) 0.43922(17) 0.0402(3) 0.1226(11) Uani 1 1 d . . . O1 O 0.3934(3) -0.06478(18) -0.1623(2) 0.0910(9) Uani 1 1 d . . . O2 O 0.1705(3) 0.07596(15) 0.15684(18) 0.0694(7) Uani 1 1 d . . . O3 O 0.4178(3) 0.24279(15) -0.07148(16) 0.0664(7) Uani 1 1 d . . . N1 N 0.2963(3) 0.14221(15) 0.02619(17) 0.0454(6) Uani 1 1 d . . . C1 C -0.2195(4) 0.3713(2) 0.0184(3) 0.0701(10) Uani 1 1 d . . . C2 C -0.1395(3) 0.2982(2) -0.0270(2) 0.0518(8) Uani 1 1 d . . . C3 C -0.1596(4) 0.2143(2) 0.0090(2) 0.0565(8) Uani 1 1 d . . . H3 H -0.2250 0.2040 0.0617 0.068 Uiso 1 1 calc R . . C4 C -0.0831(3) 0.1463(2) -0.0329(2) 0.0529(8) Uani 1 1 d . . . H4 H -0.0972 0.0903 -0.0082 0.064 Uiso 1 1 calc R . . C5 C 0.0150(3) 0.16029(18) -0.1120(2) 0.0458(7) Uani 1 1 d . . . C6 C 0.0306(3) 0.2438(2) -0.1498(2) 0.0530(8) Uani 1 1 d . . . H6 H 0.0924 0.2540 -0.2046 0.064 Uiso 1 1 calc R . . C7 C -0.0447(3) 0.3122(2) -0.1069(3) 0.0575(8) Uani 1 1 d . . . H7 H -0.0315 0.3681 -0.1320 0.069 Uiso 1 1 calc R . . C8 C 0.0912(3) 0.0856(2) -0.1598(2) 0.0508(7) Uani 1 1 d . . . H8 H 0.0398 0.0636 -0.2212 0.061 Uiso 1 1 calc R . . C9 C 0.2206(3) 0.04541(17) -0.1288(2) 0.0435(7) Uani 1 1 d . . . C10 C 0.2710(3) -0.0310(2) -0.1901(2) 0.0543(8) Uani 1 1 d . . . C11 C 0.1726(4) -0.0658(2) -0.2820(3) 0.0682(9) Uani 1 1 d . . . H11A H 0.2231 -0.1138 -0.3122 0.102 Uiso 1 1 calc R . . H11B H 0.1545 -0.0211 -0.3343 0.102 Uiso 1 1 calc R . . H11C H 0.0769 -0.0847 -0.2586 0.102 Uiso 1 1 calc R . . C12 C 0.3302(3) 0.06561(19) -0.0335(2) 0.0528(8) Uani 1 1 d . . . H12A H 0.3329 0.0162 0.0139 0.063 Uiso 1 1 calc R . . H12B H 0.4318 0.0721 -0.0573 0.063 Uiso 1 1 calc R . . C13 C 0.2187(3) 0.14100(19) 0.1175(2) 0.0456(7) Uani 1 1 d . . . C14 C 0.2093(3) 0.23240(19) 0.1517(2) 0.0450(7) Uani 1 1 d . . . C15 C 0.1385(4) 0.2689(2) 0.2337(2) 0.0591(8) Uani 1 1 d . . . H15 H 0.0868 0.2352 0.2799 0.071 Uiso 1 1 calc R . . C16 C 0.1477(4) 0.3575(3) 0.2444(3) 0.0671(10) Uani 1 1 d . . . H16 H 0.1004 0.3839 0.2990 0.081 Uiso 1 1 calc R . . C17 C 0.2240(4) 0.4084(2) 0.1774(3) 0.0669(10) Uani 1 1 d . . . H17 H 0.2276 0.4681 0.1874 0.080 Uiso 1 1 calc R . . C18 C 0.2961(4) 0.3713(2) 0.0946(2) 0.0566(8) Uani 1 1 d . . . H18 H 0.3489 0.4051 0.0490 0.068 Uiso 1 1 calc R . . C19 C 0.2861(3) 0.28333(19) 0.08317(19) 0.0441(7) Uani 1 1 d . . . C20 C 0.3447(3) 0.2252(2) 0.0021(2) 0.0452(7) 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 F1 0.224(4) 0.100(2) 0.124(2) 0.0055(16) 0.100(2) 0.066(2) F2 0.0820(15) 0.0827(17) 0.148(2) -0.0110(15) -0.0042(15) 0.0380(13) F3 0.0856(16) 0.0851(19) 0.196(3) -0.0717(19) 0.0041(17) 0.0046(13) O1 0.0840(19) 0.0820(19) 0.1044(19) -0.0369(15) -0.0065(15) 0.0381(15) O2 0.0822(16) 0.0562(14) 0.0714(14) 0.0197(11) 0.0156(12) -0.0061(12) O3 0.0751(15) 0.0701(16) 0.0585(13) -0.0027(11) 0.0325(11) -0.0100(12) N1 0.0475(13) 0.0431(14) 0.0463(13) -0.0017(10) 0.0072(10) 0.0015(10) C1 0.071(2) 0.057(2) 0.083(2) -0.0110(18) 0.010(2) 0.0112(18) C2 0.0462(16) 0.0496(18) 0.0594(17) -0.0036(14) 0.0025(13) 0.0087(13) C3 0.0554(18) 0.059(2) 0.0565(17) 0.0025(15) 0.0149(14) 0.0057(15) C4 0.0583(18) 0.0428(17) 0.0580(17) 0.0020(13) 0.0071(14) 0.0052(13) C5 0.0414(15) 0.0452(16) 0.0497(15) -0.0025(12) -0.0013(12) 0.0072(12) C6 0.0489(16) 0.055(2) 0.0564(16) 0.0030(14) 0.0109(14) -0.0004(14) C7 0.0558(18) 0.0410(16) 0.076(2) 0.0074(15) 0.0083(16) 0.0030(14) C8 0.0504(16) 0.0523(18) 0.0492(16) -0.0063(13) 0.0008(13) 0.0020(14) C9 0.0472(15) 0.0376(15) 0.0468(15) 0.0006(12) 0.0107(12) 0.0013(12) C10 0.0581(18) 0.0461(17) 0.0603(18) -0.0023(14) 0.0140(15) 0.0049(14) C11 0.078(2) 0.056(2) 0.072(2) -0.0193(16) 0.0163(18) -0.0027(17) C12 0.0518(17) 0.0454(17) 0.0612(17) -0.0042(14) 0.0059(14) 0.0117(13) C13 0.0455(15) 0.0475(17) 0.0439(15) 0.0062(12) 0.0044(12) -0.0004(13) C14 0.0439(15) 0.0540(18) 0.0370(13) 0.0013(12) 0.0039(11) -0.0016(13) C15 0.0590(18) 0.075(2) 0.0449(16) -0.0035(15) 0.0123(14) 0.0007(17) C16 0.066(2) 0.083(3) 0.0525(18) -0.0230(18) 0.0070(16) 0.0139(18) C17 0.078(2) 0.058(2) 0.064(2) -0.0176(17) -0.0040(18) 0.0067(17) C18 0.0645(19) 0.0494(19) 0.0555(17) -0.0038(14) 0.0019(15) -0.0088(14) C19 0.0458(15) 0.0501(18) 0.0361(14) -0.0040(12) 0.0021(11) -0.0024(12) C20 0.0419(15) 0.0530(18) 0.0414(14) -0.0005(12) 0.0072(12) -0.0020(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.311(4) . ? F2 C1 1.330(4) . ? F3 C1 1.321(4) . ? O1 C10 1.219(4) . ? O2 C13 1.212(3) . ? O3 C20 1.206(3) . ? N1 C20 1.392(4) . ? N1 C13 1.392(4) . ? N1 C12 1.448(3) . ? C1 C2 1.470(4) . ? C2 C3 1.389(4) . ? C2 C7 1.380(4) . ? C3 C4 1.376(4) . ? C3 H3 0.9300 . ? C4 C5 1.392(4) . ? C4 H4 0.9300 . ? C5 C6 1.386(4) . ? C5 C8 1.487(4) . ? C6 C7 1.380(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.324(4) . ? C8 H8 0.9300 . ? C9 C10 1.499(4) . ? C9 C12 1.511(4) . ? C10 C11 1.489(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.479(4) . ? C14 C19 1.388(4) . ? C14 C15 1.375(4) . ? C15 C16 1.375(5) . ? C15 H15 0.9300 . ? C16 C17 1.372(5) . ? C16 H16 0.9300 . ? C17 C18 1.393(4) . ? C17 H17 0.9300 . ? C18 C19 1.367(4) . ? C18 H18 0.9300 . ? C19 C20 1.488(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 C20 N1 C13 112.0(2) . . ? C20 N1 C12 123.8(2) . . ? C13 N1 C12 124.1(2) . . ? F2 C1 F3 103.2(3) . . ? F2 C1 F1 104.2(3) . . ? F3 C1 F1 107.4(3) . . ? F2 C1 C2 113.4(3) . . ? F3 C1 C2 113.4(3) . . ? F1 C1 C2 114.3(3) . . ? C3 C2 C7 119.1(3) . . ? C3 C2 C1 120.5(3) . . ? C7 C2 C1 120.3(3) . . ? C2 C3 C4 120.3(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 118.6(3) . . ? C4 C5 C8 120.0(3) . . ? C6 C5 C8 121.3(3) . . ? C7 C6 C5 120.6(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C2 120.6(3) . . ? C6 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? C9 C8 C5 130.2(3) . . ? C9 C8 H8 114.9 . . ? C5 C8 H8 114.9 . . ? C8 C9 C10 119.9(3) . . ? C8 C9 C12 127.8(2) . . ? C10 C9 C12 112.3(2) . . ? O1 C10 C9 118.6(3) . . ? O1 C10 C11 120.7(3) . . ? C9 C10 C11 120.7(3) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 C9 116.1(2) . . ? N1 C12 H12A 108.3 . . ? C9 C12 H12A 108.3 . . ? N1 C12 H12B 108.3 . . ? C9 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? O2 C13 N1 124.4(3) . . ? O2 C13 C14 129.7(3) . . ? N1 C13 C14 105.9(2) . . ? C19 C14 C15 121.0(3) . . ? C19 C14 C13 108.3(2) . . ? C15 C14 C13 130.7(3) . . ? C16 C15 C14 117.1(3) . . ? C16 C15 H15 121.4 . . ? C14 C15 H15 121.4 . . ? C15 C16 C17 122.4(3) . . ? C15 C16 H16 118.8 . . ? C17 C16 H16 118.8 . . ? C16 C17 C18 120.5(3) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C19 C18 C17 117.3(3) . . ? C19 C18 H18 121.4 . . ? C17 C18 H18 121.4 . . ? C14 C19 C18 121.7(3) . . ? C14 C19 C20 107.8(3) . . ? C18 C19 C20 130.4(3) . . ? O3 C20 N1 124.7(3) . . ? O3 C20 C19 129.5(3) . . ? N1 C20 C19 105.8(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.296 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.074 data_10633 _database_code_depnum_ccdc_archive 'CCDC 770519' #TrackingRef '10633.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 Br1 N2 O3' _chemical_formula_sum 'C15 H15 Br N2 O3' _chemical_formula_weight 351.20 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' Br Br -0.2901 2.4595 '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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8110(2) _cell_length_b 8.3322(2) _cell_length_c 12.4088(4) _cell_angle_alpha 70.7750(10) _cell_angle_beta 89.2880(10) _cell_angle_gamma 78.7200(10) _cell_volume 746.65(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5299 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 2.764 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3747 _exptl_absorpt_correction_T_max 0.436 _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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6500 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2612 _reflns_number_gt 2144 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0352P)^2^+1.4822P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2612 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 Br1 Br 0.3162 0.2842 0.4972 0.0710(2) Uani 1 1 d . . . O1 O 0.1972(5) -0.5045(5) 1.2186(3) 0.0777(11) Uani 1 1 d . . . O2 O -0.1033(4) -0.1770(4) 0.9054(3) 0.0620(8) Uani 1 1 d . . . O3 O 0.3757(5) -0.4642(5) 0.7838(3) 0.0805(11) Uani 1 1 d . . . N1 N 0.1541(4) -0.3368(4) 0.8737(3) 0.0444(8) Uani 1 1 d . . . N2 N 0.1315(5) -0.2730(5) 0.6857(3) 0.0522(9) Uani 1 1 d . . . C1 C 0.3160(6) 0.1533(5) 0.6549(3) 0.0485(10) Uani 1 1 d . . . C2 C 0.4268(6) -0.0048(6) 0.6978(4) 0.0544(11) Uani 1 1 d . . . H2 H 0.5023 -0.0470 0.6503 0.065 Uiso 1 1 calc R . . C3 C 0.4259(6) -0.1016(6) 0.8121(4) 0.0522(10) Uani 1 1 d . . . H3 H 0.5025 -0.2082 0.8417 0.063 Uiso 1 1 calc R . . C4 C 0.3117(5) -0.0407(5) 0.8828(3) 0.0444(9) Uani 1 1 d . . . C5 C 0.2056(6) 0.1230(5) 0.8384(4) 0.0515(10) Uani 1 1 d . . . H5 H 0.1336 0.1683 0.8861 0.062 Uiso 1 1 calc R . . C6 C 0.2058(6) 0.2194(5) 0.7239(4) 0.0517(10) Uani 1 1 d . . . H6 H 0.1322 0.3277 0.6941 0.062 Uiso 1 1 calc R . . C7 C 0.2993(5) -0.1406(5) 1.0047(3) 0.0458(9) Uani 1 1 d . . . H7 H 0.3176 -0.0849 1.0560 0.055 Uiso 1 1 calc R . . C8 C 0.2657(5) -0.2993(5) 1.0516(3) 0.0446(9) Uani 1 1 d . . . C9 C 0.2504(5) -0.3707(5) 1.1773(4) 0.0498(10) Uani 1 1 d . . . C10 C 0.2984(7) -0.2783(6) 1.2539(4) 0.0596(12) Uani 1 1 d . . . H10A H 0.2812 -0.3423 1.3318 0.089 Uiso 1 1 calc R . . H10B H 0.2259 -0.1643 1.2329 0.089 Uiso 1 1 calc R . . H10C H 0.4188 -0.2690 1.2462 0.089 Uiso 1 1 calc R . . C11 C 0.2302(7) -0.4193(5) 0.9897(4) 0.0640(13) Uani 1 1 d . . . H11A H 0.3396 -0.4966 0.9877 0.077 Uiso 1 1 calc R . . H11B H 0.1524 -0.4902 1.0342 0.077 Uiso 1 1 calc R . . C12 C -0.0008(5) -0.2238(5) 0.8419(3) 0.0443(9) Uani 1 1 d . . . C13 C -0.0196(6) -0.1690(5) 0.7140(3) 0.0493(10) Uani 1 1 d . . . H13A H -0.1265 -0.1928 0.6893 0.059 Uiso 1 1 calc R . . H13B H -0.0197 -0.0463 0.6792 0.059 Uiso 1 1 calc R . . C14 C 0.1784(8) -0.2564(8) 0.5707(4) 0.0817(16) Uani 1 1 d . . . H14A H 0.0829 -0.1842 0.5182 0.123 Uiso 1 1 calc R . . H14B H 0.2041 -0.3692 0.5625 0.123 Uiso 1 1 calc R . . H14C H 0.2796 -0.2049 0.5546 0.123 Uiso 1 1 calc R . . C15 C 0.2368(6) -0.3686(6) 0.7789(4) 0.0536(11) 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 Br1 0.0949(4) 0.0740(4) 0.0448(3) -0.0132(2) 0.0143(2) -0.0310(3) O1 0.108(3) 0.072(2) 0.0533(19) -0.0042(17) 0.0015(19) -0.048(2) O2 0.0617(19) 0.068(2) 0.064(2) -0.0319(17) 0.0130(16) -0.0132(16) O3 0.059(2) 0.077(2) 0.110(3) -0.050(2) -0.006(2) 0.0106(19) N1 0.051(2) 0.0389(17) 0.0424(18) -0.0122(14) -0.0056(15) -0.0091(15) N2 0.053(2) 0.060(2) 0.046(2) -0.0220(17) 0.0032(16) -0.0100(18) C1 0.057(3) 0.051(2) 0.041(2) -0.0123(18) 0.0052(19) -0.026(2) C2 0.055(3) 0.057(3) 0.058(3) -0.025(2) 0.017(2) -0.018(2) C3 0.052(2) 0.045(2) 0.060(3) -0.014(2) 0.004(2) -0.0148(19) C4 0.049(2) 0.042(2) 0.045(2) -0.0142(18) 0.0008(18) -0.0173(19) C5 0.065(3) 0.045(2) 0.045(2) -0.0153(19) 0.011(2) -0.012(2) C6 0.055(3) 0.043(2) 0.052(2) -0.0109(19) 0.001(2) -0.0076(19) C7 0.048(2) 0.047(2) 0.044(2) -0.0156(18) -0.0003(18) -0.0129(18) C8 0.047(2) 0.040(2) 0.044(2) -0.0107(17) -0.0062(18) -0.0082(18) C9 0.047(2) 0.048(2) 0.048(2) -0.0078(19) -0.0016(19) -0.0091(19) C10 0.076(3) 0.054(3) 0.045(2) -0.014(2) -0.002(2) -0.007(2) C11 0.093(4) 0.038(2) 0.053(3) -0.0028(19) -0.028(2) -0.012(2) C12 0.048(2) 0.041(2) 0.048(2) -0.0156(18) 0.0038(19) -0.0150(18) C13 0.053(2) 0.047(2) 0.046(2) -0.0146(19) -0.0048(19) -0.0082(19) C14 0.089(4) 0.110(5) 0.059(3) -0.041(3) 0.022(3) -0.029(3) C15 0.050(3) 0.049(2) 0.068(3) -0.028(2) 0.001(2) -0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.901(4) . ? O1 C9 1.216(5) . ? O2 C12 1.216(5) . ? O3 C15 1.203(5) . ? N1 C12 1.352(5) . ? N1 C15 1.410(6) . ? N1 C11 1.452(5) . ? N2 C15 1.345(6) . ? N2 C13 1.434(5) . ? N2 C14 1.438(6) . ? C1 C2 1.368(6) . ? C1 C6 1.373(6) . ? C2 C3 1.382(6) . ? C2 H2 0.9300 . ? C3 C4 1.386(6) . ? C3 H3 0.9300 . ? C4 C5 1.387(6) . ? C4 C7 1.479(5) . ? C5 C6 1.383(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.334(5) . ? C7 H7 0.9300 . ? C8 C9 1.488(6) . ? C8 C11 1.511(6) . ? C9 C10 1.497(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.500(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 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 C12 N1 C15 111.6(3) . . ? C12 N1 C11 125.9(4) . . ? C15 N1 C11 122.5(4) . . ? C15 N2 C13 111.5(3) . . ? C15 N2 C14 123.8(4) . . ? C13 N2 C14 124.0(4) . . ? C2 C1 C6 121.1(4) . . ? C2 C1 Br1 119.3(3) . . ? C6 C1 Br1 119.5(3) . . ? C1 C2 C3 119.6(4) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 120.4(4) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 118.8(4) . . ? C5 C4 C7 118.0(4) . . ? C3 C4 C7 123.2(4) . . ? C6 C5 C4 120.7(4) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C1 C6 C5 119.2(4) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C8 C7 C4 129.4(4) . . ? C8 C7 H7 115.3 . . ? C4 C7 H7 115.3 . . ? C7 C8 C9 119.8(4) . . ? C7 C8 C11 127.0(4) . . ? C9 C8 C11 113.1(3) . . ? O1 C9 C8 120.0(4) . . ? O1 C9 C10 119.4(4) . . ? C8 C9 C10 120.6(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C8 116.3(3) . . ? N1 C11 H11A 108.2 . . ? C8 C11 H11A 108.2 . . ? N1 C11 H11B 108.2 . . ? C8 C11 H11B 108.2 . . ? H11A C11 H11B 107.4 . . ? O2 C12 N1 126.2(4) . . ? O2 C12 C13 127.4(4) . . ? N1 C12 C13 106.4(3) . . ? N2 C13 C12 103.3(3) . . ? N2 C13 H13A 111.1 . . ? C12 C13 H13A 111.1 . . ? N2 C13 H13B 111.1 . . ? C12 C13 H13B 111.1 . . ? H13A C13 H13B 109.1 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O3 C15 N2 128.0(4) . . ? O3 C15 N1 124.9(4) . . ? N2 C15 N1 107.0(4) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.059 _refine_diff_density_min -1.190 _refine_diff_density_rms 0.064 data_10802 _database_code_depnum_ccdc_archive 'CCDC 775300' #TrackingRef '10802.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H20 N2 O3' _chemical_formula_sum 'C21 H20 N2 O3' _chemical_formula_weight 348.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 9.8444(4) _cell_length_b 10.7537(4) _cell_length_c 17.1394(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.088(2) _cell_angle_gamma 90.00 _cell_volume 1786.39(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5003 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.35 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9303 _exptl_absorpt_correction_T_max 1.049 _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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9433 _diffrn_reflns_av_R_equivalents 0.0863 _diffrn_reflns_av_sigmaI/netI 0.1032 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.36 _reflns_number_total 3213 _reflns_number_gt 1647 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1349P)^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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3213 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1560 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.2440 _refine_ls_wR_factor_gt 0.1618 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 0.9640(3) 0.0967(3) 0.83213(18) 0.0688(10) Uani 1 1 d . . . O2 O 0.3726(3) -0.0817(3) 0.70827(19) 0.0753(11) Uani 1 1 d . . . O3 O 0.7838(3) -0.2031(2) 0.67232(16) 0.0518(8) Uani 1 1 d . . . N1 N 0.8307(3) 0.0636(3) 0.70998(17) 0.0404(8) Uani 1 1 d . . . N2 N 0.8449(3) 0.0542(3) 0.62863(18) 0.0424(9) Uani 1 1 d . . . C1 C 0.9547(4) 0.0862(4) 0.7613(3) 0.0521(12) Uani 1 1 d . . . C2 C 1.0634(4) 0.0889(5) 0.7098(3) 0.0631(14) Uani 1 1 d . . . H2A H 1.1451 0.0436 0.7342 0.076 Uiso 1 1 calc R . . H2B H 1.0891 0.1737 0.6997 0.076 Uiso 1 1 calc R . . C3 C 0.9945(4) 0.0262(4) 0.6346(3) 0.0576(12) Uani 1 1 d . . . H3A H 1.0292 0.0592 0.5892 0.069 Uiso 1 1 calc R . . H3B H 1.0106 -0.0628 0.6374 0.069 Uiso 1 1 calc R . . C4 C 0.7997(4) 0.1653(4) 0.5844(2) 0.0399(10) Uani 1 1 d . . . C5 C 0.7655(4) 0.2748(4) 0.6180(2) 0.0459(10) Uani 1 1 d . . . H5 H 0.7718 0.2809 0.6726 0.055 Uiso 1 1 calc R . . C6 C 0.7215(4) 0.3761(4) 0.5698(3) 0.0581(12) Uani 1 1 d . . . H6 H 0.6974 0.4497 0.5924 0.070 Uiso 1 1 calc R . . C7 C 0.7134(5) 0.3685(5) 0.4889(3) 0.0625(13) Uani 1 1 d . . . H7 H 0.6855 0.4372 0.4572 0.075 Uiso 1 1 calc R . . C8 C 0.7467(4) 0.2592(5) 0.4553(3) 0.0609(13) Uani 1 1 d . . . H8 H 0.7406 0.2538 0.4007 0.073 Uiso 1 1 calc R . . C9 C 0.7890(4) 0.1575(4) 0.5023(2) 0.0508(11) Uani 1 1 d . . . H9 H 0.8105 0.0835 0.4792 0.061 Uiso 1 1 calc R . . C10 C 0.7073(4) 0.0447(3) 0.7354(2) 0.0384(10) Uani 1 1 d . . . H10 H 0.7011 0.0762 0.7852 0.046 Uiso 1 1 calc R . . C11 C 0.5938(4) -0.0142(4) 0.6968(2) 0.0374(10) Uani 1 1 d . . . C12 C 0.4715(4) -0.0177(4) 0.7353(2) 0.0472(11) Uani 1 1 d . . . C13 C 0.4653(5) 0.0611(5) 0.8080(2) 0.0628(13) Uani 1 1 d . . . H13A H 0.3791 0.0471 0.8255 0.094 Uiso 1 1 calc R . . H13B H 0.4730 0.1474 0.7950 0.094 Uiso 1 1 calc R . . H13C H 0.5400 0.0387 0.8496 0.094 Uiso 1 1 calc R . . C14 C 0.5855(4) -0.0817(4) 0.6196(2) 0.0433(10) Uani 1 1 d . . . H14A H 0.5809 -0.0204 0.5776 0.052 Uiso 1 1 calc R . . H14B H 0.4999 -0.1285 0.6099 0.052 Uiso 1 1 calc R . . C15 C 0.7021(4) -0.1694(4) 0.6137(2) 0.0405(10) Uani 1 1 d . . . C16 C 0.7150(4) -0.2172(4) 0.5336(2) 0.0423(10) Uani 1 1 d . . . C17 C 0.8418(4) -0.2628(4) 0.5198(2) 0.0494(11) Uani 1 1 d . . . H17 H 0.9179 -0.2614 0.5604 0.059 Uiso 1 1 calc R . . C18 C 0.8551(5) -0.3092(4) 0.4475(3) 0.0581(13) Uani 1 1 d . . . H18 H 0.9400 -0.3392 0.4392 0.070 Uiso 1 1 calc R . . C19 C 0.7425(5) -0.3116(4) 0.3864(3) 0.0606(13) Uani 1 1 d . . . H19 H 0.7516 -0.3430 0.3370 0.073 Uiso 1 1 calc R . . C20 C 0.6181(5) -0.2678(4) 0.3991(3) 0.0594(12) Uani 1 1 d . . . H20 H 0.5422 -0.2702 0.3584 0.071 Uiso 1 1 calc R . . C21 C 0.6042(4) -0.2197(4) 0.4721(2) 0.0514(11) Uani 1 1 d . . . H21 H 0.5193 -0.1888 0.4797 0.062 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 0.056(2) 0.091(3) 0.052(2) 0.0057(18) -0.0116(14) -0.0083(18) O2 0.053(2) 0.094(3) 0.084(2) -0.036(2) 0.0253(17) -0.0310(19) O3 0.0577(18) 0.0443(18) 0.0526(18) 0.0076(14) 0.0078(14) 0.0079(14) N1 0.0304(18) 0.049(2) 0.0407(18) 0.0042(16) 0.0041(14) -0.0041(16) N2 0.0352(19) 0.046(2) 0.047(2) 0.0030(17) 0.0102(15) 0.0021(16) C1 0.036(2) 0.053(3) 0.063(3) 0.011(2) -0.004(2) -0.006(2) C2 0.036(2) 0.075(4) 0.076(3) 0.013(3) 0.003(2) -0.003(2) C3 0.041(3) 0.058(3) 0.078(3) 0.003(3) 0.023(2) 0.005(2) C4 0.034(2) 0.046(3) 0.040(2) -0.002(2) 0.0071(17) -0.0052(19) C5 0.051(2) 0.046(3) 0.039(2) -0.005(2) 0.0042(18) -0.003(2) C6 0.063(3) 0.047(3) 0.059(3) -0.001(2) -0.006(2) 0.000(2) C7 0.070(3) 0.060(3) 0.049(3) 0.016(3) -0.014(2) -0.013(3) C8 0.065(3) 0.077(4) 0.039(2) 0.010(3) 0.004(2) -0.018(3) C9 0.048(3) 0.060(3) 0.049(3) -0.009(2) 0.018(2) -0.010(2) C10 0.040(2) 0.036(2) 0.040(2) 0.0005(18) 0.0096(17) 0.0009(19) C11 0.031(2) 0.041(2) 0.039(2) -0.0016(18) 0.0043(16) -0.0001(18) C12 0.039(3) 0.050(3) 0.053(3) -0.006(2) 0.0101(19) -0.001(2) C13 0.053(3) 0.079(4) 0.060(3) -0.020(3) 0.022(2) -0.014(3) C14 0.035(2) 0.049(3) 0.045(2) -0.008(2) 0.0075(17) -0.004(2) C15 0.039(2) 0.032(2) 0.051(3) 0.002(2) 0.0111(19) -0.0048(19) C16 0.045(2) 0.040(2) 0.045(2) 0.002(2) 0.0156(19) -0.001(2) C17 0.047(3) 0.043(3) 0.059(3) 0.001(2) 0.015(2) 0.000(2) C18 0.052(3) 0.057(3) 0.072(3) -0.007(3) 0.030(2) 0.001(2) C19 0.073(3) 0.057(3) 0.057(3) -0.011(2) 0.026(2) -0.010(3) C20 0.056(3) 0.069(3) 0.053(3) -0.009(2) 0.008(2) -0.002(3) C21 0.047(3) 0.055(3) 0.054(3) -0.008(2) 0.014(2) 0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.206(5) . ? O2 C12 1.216(5) . ? O3 C15 1.226(4) . ? N1 C10 1.376(5) . ? N1 C1 1.396(5) . ? N1 N2 1.429(4) . ? N2 C4 1.443(5) . ? N2 C3 1.489(5) . ? C1 C2 1.502(6) . ? C2 C3 1.507(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.378(5) . ? C4 C9 1.395(5) . ? C5 C6 1.389(6) . ? C5 H5 0.9300 . ? C6 C7 1.377(6) . ? C6 H6 0.9300 . ? C7 C8 1.373(6) . ? C7 H7 0.9300 . ? C8 C9 1.378(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.353(5) . ? C10 H10 0.9300 . ? C11 C12 1.471(5) . ? C11 C14 1.499(5) . ? C12 C13 1.518(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.503(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.493(5) . ? C16 C21 1.378(5) . ? C16 C17 1.398(5) . ? C17 C18 1.363(5) . ? C17 H17 0.9300 . ? C18 C19 1.385(6) . ? C18 H18 0.9300 . ? C19 C20 1.365(6) . ? C19 H19 0.9300 . ? C20 C21 1.382(5) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 N1 C1 123.3(3) . . ? C10 N1 N2 122.8(3) . . ? C1 N1 N2 113.8(3) . . ? N1 N2 C4 112.4(3) . . ? N1 N2 C3 102.3(3) . . ? C4 N2 C3 114.4(3) . . ? O1 C1 N1 123.7(4) . . ? O1 C1 C2 130.8(4) . . ? N1 C1 C2 105.5(4) . . ? C1 C2 C3 103.5(3) . . ? C1 C2 H2A 111.1 . . ? C3 C2 H2A 111.1 . . ? C1 C2 H2B 111.1 . . ? C3 C2 H2B 111.1 . . ? H2A C2 H2B 109.0 . . ? N2 C3 C2 105.0(3) . . ? N2 C3 H3A 110.7 . . ? C2 C3 H3A 110.7 . . ? N2 C3 H3B 110.7 . . ? C2 C3 H3B 110.7 . . ? H3A C3 H3B 108.8 . . ? C5 C4 C9 119.5(4) . . ? C5 C4 N2 124.3(3) . . ? C9 C4 N2 116.2(4) . . ? C4 C5 C6 119.7(4) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 120.6(4) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C8 C7 C6 119.8(4) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.3(4) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C4 120.2(4) . . ? C8 C9 H9 119.9 . . ? C4 C9 H9 119.9 . . ? C11 C10 N1 127.8(4) . . ? C11 C10 H10 116.1 . . ? N1 C10 H10 116.1 . . ? C10 C11 C12 117.5(4) . . ? C10 C11 C14 124.9(3) . . ? C12 C11 C14 117.5(3) . . ? O2 C12 C11 120.5(4) . . ? O2 C12 C13 118.9(4) . . ? C11 C12 C13 120.5(4) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 C15 116.0(3) . . ? C11 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? C11 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? O3 C15 C16 120.2(4) . . ? O3 C15 C14 122.0(3) . . ? C16 C15 C14 117.8(3) . . ? C21 C16 C17 118.3(4) . . ? C21 C16 C15 121.8(4) . . ? C17 C16 C15 119.9(4) . . ? C18 C17 C16 120.9(4) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 120.1(4) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C20 C19 C18 119.6(4) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C21 120.5(4) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C16 C21 C20 120.5(4) . . ? C16 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.347 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.137 data_10837 _database_code_depnum_ccdc_archive 'CCDC 778973' #TrackingRef '10837.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 N2 O6' _chemical_formula_sum 'C19 H16 N2 O6' _chemical_formula_weight 368.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a b' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y, -z+1/2' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y, z-1/2' 'x-1/2, -y-1/2, z' _cell_length_a 11.2975(2) _cell_length_b 15.8036(3) _cell_length_c 20.1450(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3596.71(14) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11999 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8766 #_exptl_absorpt_correction_T_max 1.0703 _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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15674 _diffrn_reflns_av_R_equivalents 0.0766 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3178 _reflns_number_gt 2178 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1217P)^2^+0.1372P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3178 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0913 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1938 _refine_ls_wR_factor_gt 0.1566 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.003 _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 0.7636(3) 0.18431(18) 0.25766(13) 0.0516(7) Uani 1 1 d . . . C2 C 0.6701(3) 0.2402(2) 0.25791(15) 0.0647(9) Uani 1 1 d . . . H2 H 0.6542 0.2733 0.2950 0.078 Uiso 1 1 calc R . . C3 C 0.6009(3) 0.24590(19) 0.20192(14) 0.0602(8) Uani 1 1 d . . . H3 H 0.5371 0.2831 0.2013 0.072 Uiso 1 1 calc R . . C4 C 0.6250(2) 0.19675(15) 0.14632(12) 0.0416(6) Uani 1 1 d . . . C5 C 0.7193(2) 0.14142(18) 0.14831(14) 0.0523(7) Uani 1 1 d . . . H5 H 0.7361 0.1080 0.1115 0.063 Uiso 1 1 calc R . . C6 C 0.7891(3) 0.13504(19) 0.20437(15) 0.0571(8) Uani 1 1 d . . . H6 H 0.8526 0.0976 0.2056 0.069 Uiso 1 1 calc R . . C7 C 0.5521(2) 0.20626(17) 0.08385(13) 0.0450(7) Uani 1 1 d . . . H7 H 0.5967 0.1824 0.0466 0.054 Uiso 1 1 calc R . . C8 C 0.4316(2) 0.16311(16) 0.08712(12) 0.0423(6) Uani 1 1 d . . . H8 H 0.3862 0.1896 0.1230 0.051 Uiso 1 1 calc R . . C9 C 0.3622(2) 0.17385(17) 0.02305(13) 0.0468(7) Uani 1 1 d . . . C10 C 0.4223(3) 0.1663(2) -0.04264(14) 0.0637(9) Uani 1 1 d . . . H10A H 0.3655 0.1746 -0.0775 0.096 Uiso 1 1 calc R . . H10B H 0.4569 0.1110 -0.0467 0.096 Uiso 1 1 calc R . . H10C H 0.4832 0.2084 -0.0460 0.096 Uiso 1 1 calc R . . C11 C 0.4423(2) 0.06799(17) 0.10263(14) 0.0484(7) Uani 1 1 d . . . H11A H 0.4877 0.0406 0.0679 0.058 Uiso 1 1 calc R . . H11B H 0.4846 0.0606 0.1441 0.058 Uiso 1 1 calc R . . C12 C 0.2724(2) -0.01565(16) 0.05601(12) 0.0459(7) Uani 1 1 d . . . C13 C 0.1540(2) -0.04075(16) 0.08141(12) 0.0448(7) Uani 1 1 d . . . C14 C 0.0651(3) -0.0856(2) 0.05126(15) 0.0618(8) Uani 1 1 d . . . H14 H 0.0727 -0.1051 0.0079 0.074 Uiso 1 1 calc R . . C15 C -0.0361(3) -0.1005(2) 0.08795(17) 0.0701(9) Uani 1 1 d . . . H15 H -0.0983 -0.1302 0.0687 0.084 Uiso 1 1 calc R . . C16 C -0.0466(3) -0.0726(2) 0.15200(16) 0.0697(9) Uani 1 1 d . . . H16 H -0.1156 -0.0841 0.1755 0.084 Uiso 1 1 calc R . . C17 C 0.0431(3) -0.0276(2) 0.18252(14) 0.0598(8) Uani 1 1 d . . . H17 H 0.0355 -0.0084 0.2260 0.072 Uiso 1 1 calc R . . C18 C 0.1442(2) -0.01221(16) 0.14615(12) 0.0449(7) Uani 1 1 d . . . C19 C 0.2544(2) 0.03315(17) 0.16335(12) 0.0462(7) Uani 1 1 d . . . N1 N 0.8393(3) 0.1789(2) 0.31694(15) 0.0707(8) Uani 1 1 d . . . N2 N 0.32714(19) 0.02819(13) 0.10757(10) 0.0453(6) Uani 1 1 d . . . O1 O 0.9267(3) 0.13255(19) 0.31419(13) 0.0953(9) Uani 1 1 d . . . O2 O 0.8116(3) 0.2192(2) 0.36624(14) 0.1124(11) Uani 1 1 d . . . O3 O 0.52736(18) 0.29282(12) 0.06994(10) 0.0597(6) Uani 1 1 d . . . H3' H 0.5559 0.3226 0.0992 0.089 Uiso 1 1 calc R . . O4 O 0.25573(17) 0.18342(15) 0.02575(11) 0.0715(7) Uani 1 1 d . . . O5 O 0.31693(18) -0.02867(13) 0.00228(10) 0.0632(6) Uani 1 1 d . . . O6 O 0.28240(19) 0.06787(14) 0.21436(9) 0.0662(6) 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 0.0522(17) 0.0585(17) 0.0440(15) 0.0048(13) -0.0109(13) -0.0152(15) C2 0.065(2) 0.073(2) 0.0566(18) -0.0193(15) -0.0042(15) -0.0024(18) C3 0.0512(17) 0.0668(19) 0.0625(19) -0.0107(15) -0.0041(14) 0.0131(16) C4 0.0329(14) 0.0444(14) 0.0474(15) 0.0003(11) 0.0000(11) -0.0036(11) C5 0.0481(17) 0.0582(17) 0.0506(16) -0.0099(13) -0.0059(13) 0.0040(14) C6 0.0497(17) 0.0593(17) 0.0622(19) 0.0002(14) -0.0107(14) 0.0084(14) C7 0.0355(15) 0.0517(16) 0.0478(15) 0.0052(12) 0.0003(11) 0.0019(12) C8 0.0339(14) 0.0483(15) 0.0446(14) -0.0011(11) 0.0011(10) 0.0008(11) C9 0.0344(15) 0.0524(16) 0.0536(16) 0.0015(12) -0.0038(12) 0.0032(12) C10 0.0583(19) 0.091(2) 0.0417(16) 0.0030(14) -0.0004(13) 0.0014(17) C11 0.0381(15) 0.0522(16) 0.0548(16) 0.0017(12) -0.0051(12) -0.0033(12) C12 0.0471(16) 0.0469(15) 0.0436(14) -0.0054(12) 0.0056(12) -0.0011(12) C13 0.0430(15) 0.0467(14) 0.0446(15) -0.0062(11) 0.0030(12) -0.0034(12) C14 0.0566(19) 0.072(2) 0.0570(17) -0.0147(15) 0.0060(15) -0.0123(16) C15 0.0507(19) 0.081(2) 0.078(2) -0.0147(18) 0.0087(16) -0.0187(17) C16 0.0511(19) 0.080(2) 0.078(2) -0.0053(17) 0.0183(16) -0.0157(17) C17 0.0618(19) 0.0683(18) 0.0493(16) -0.0058(14) 0.0150(14) 0.0016(16) C18 0.0454(15) 0.0466(15) 0.0426(14) -0.0014(11) 0.0042(11) -0.0011(12) C19 0.0523(16) 0.0484(15) 0.0378(14) -0.0004(12) -0.0019(12) 0.0007(13) N1 0.070(2) 0.0787(19) 0.0633(18) 0.0100(15) -0.0221(15) -0.0211(17) N2 0.0413(13) 0.0510(13) 0.0436(12) 0.0004(10) -0.0003(10) -0.0082(10) O1 0.0875(19) 0.110(2) 0.0883(19) 0.0130(15) -0.0392(15) 0.0035(17) O2 0.117(2) 0.155(3) 0.0653(17) -0.0317(17) -0.0297(16) 0.001(2) O3 0.0539(12) 0.0533(12) 0.0717(13) 0.0143(9) -0.0090(10) -0.0017(9) O4 0.0381(12) 0.1029(18) 0.0735(14) -0.0056(13) -0.0068(10) 0.0159(11) O5 0.0594(13) 0.0771(14) 0.0531(12) -0.0176(10) 0.0172(10) -0.0092(11) O6 0.0768(15) 0.0791(15) 0.0427(11) -0.0106(10) -0.0051(10) -0.0105(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.357(4) . ? C1 C2 1.376(4) . ? C1 N1 1.472(4) . ? C2 C3 1.376(4) . ? C2 H2 0.9300 . ? C3 C4 1.390(4) . ? C3 H3 0.9300 . ? C4 C5 1.379(4) . ? C4 C7 1.511(3) . ? C5 C6 1.381(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O3 1.424(3) . ? C7 C8 1.524(4) . ? C7 H7 0.9800 . ? C8 C9 1.519(3) . ? C8 C11 1.540(4) . ? C8 H8 0.9800 . ? C9 O4 1.214(3) . ? C9 C10 1.492(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 N2 1.449(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O5 1.211(3) . ? C12 N2 1.393(3) . ? C12 C13 1.486(4) . ? C13 C14 1.371(4) . ? C13 C18 1.385(3) . ? C14 C15 1.382(4) . ? C14 H14 0.9300 . ? C15 C16 1.369(4) . ? C15 H15 0.9300 . ? C16 C17 1.382(4) . ? C16 H16 0.9300 . ? C17 C18 1.378(4) . ? C17 H17 0.9300 . ? C18 C19 1.478(4) . ? C19 O6 1.207(3) . ? C19 N2 1.395(3) . ? N1 O2 1.221(4) . ? N1 O1 1.230(4) . ? O3 H3' 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 122.3(3) . . ? C6 C1 N1 119.0(3) . . ? C2 C1 N1 118.7(3) . . ? C3 C2 C1 118.4(3) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 120.8(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 118.8(2) . . ? C5 C4 C7 120.5(2) . . ? C3 C4 C7 120.6(2) . . ? C6 C5 C4 120.7(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C1 C6 C5 118.9(3) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? O3 C7 C4 111.5(2) . . ? O3 C7 C8 105.2(2) . . ? C4 C7 C8 114.0(2) . . ? O3 C7 H7 108.7 . . ? C4 C7 H7 108.7 . . ? C8 C7 H7 108.7 . . ? C9 C8 C7 112.0(2) . . ? C9 C8 C11 108.8(2) . . ? C7 C8 C11 112.0(2) . . ? C9 C8 H8 108.0 . . ? C7 C8 H8 108.0 . . ? C11 C8 H8 108.0 . . ? O4 C9 C10 120.0(2) . . ? O4 C9 C8 119.1(2) . . ? C10 C9 C8 120.7(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C8 111.5(2) . . ? N2 C11 H11A 109.3 . . ? C8 C11 H11A 109.3 . . ? N2 C11 H11B 109.3 . . ? C8 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? O5 C12 N2 124.5(3) . . ? O5 C12 C13 129.5(2) . . ? N2 C12 C13 106.0(2) . . ? C14 C13 C18 121.8(3) . . ? C14 C13 C12 130.1(2) . . ? C18 C13 C12 108.1(2) . . ? C13 C14 C15 117.2(3) . . ? C13 C14 H14 121.4 . . ? C15 C14 H14 121.4 . . ? C16 C15 C14 121.4(3) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 121.5(3) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C18 C17 C16 117.5(3) . . ? C18 C17 H17 121.3 . . ? C16 C17 H17 121.3 . . ? C17 C18 C13 120.7(3) . . ? C17 C18 C19 131.2(2) . . ? C13 C18 C19 108.1(2) . . ? O6 C19 N2 123.8(3) . . ? O6 C19 C18 129.9(3) . . ? N2 C19 C18 106.3(2) . . ? O2 N1 O1 123.6(3) . . ? O2 N1 C1 118.7(3) . . ? O1 N1 C1 117.7(3) . . ? C12 N2 C19 111.5(2) . . ? C12 N2 C11 124.3(2) . . ? C19 N2 C11 124.1(2) . . ? C7 O3 H3' 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.486 _refine_diff_density_min -0.543 _refine_diff_density_rms 0.161 # Attachment 'a10539.cif' data_a10539 _database_code_depnum_ccdc_archive 'CCDC 778974' #TrackingRef 'a10539.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 Cl N O4' _chemical_formula_sum 'C19 H16 Cl N O4' _chemical_formula_weight 357.78 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.8329(3) _cell_length_b 16.6085(6) _cell_length_c 13.2043(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.014(2) _cell_angle_gamma 90.00 _cell_volume 1686.14(11) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8683 _exptl_absorpt_correction_T_max 0.9241 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _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 10425 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 24.96 _reflns_number_total 2918 _reflns_number_gt 2423 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^+0.4627P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2918 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1432 _refine_ls_wR_factor_gt 0.1190 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4601(3) 0.67404(14) -0.05993(16) 0.0367(6) Uani 1 1 d . . . C2 C 0.5027(4) 0.59361(15) -0.06934(17) 0.0455(6) Uani 1 1 d . . . H2 H 0.4145 0.5536 -0.0775 0.055 Uiso 1 1 calc R . . C3 C 0.6731(4) 0.57220(15) -0.06672(18) 0.0483(7) Uani 1 1 d . . . H3 H 0.7034 0.5171 -0.0716 0.058 Uiso 1 1 calc R . . C4 C 0.7998(4) 0.63078(14) -0.05697(17) 0.0415(6) Uani 1 1 d . . . H4 H 0.9172 0.6163 -0.0569 0.050 Uiso 1 1 calc R . . C5 C 0.7556(3) 0.71124(13) -0.04723(16) 0.0324(5) Uani 1 1 d . . . H5 H 0.8440 0.7511 -0.0410 0.039 Uiso 1 1 calc R . . C6 C 0.5862(3) 0.73466(12) -0.04643(14) 0.0276(5) Uani 1 1 d . . . C7 C 0.5388(3) 0.82211(12) -0.03225(15) 0.0279(5) Uani 1 1 d . . . H7 H 0.4384 0.8366 -0.0881 0.033 Uiso 1 1 calc R . . C8 C 0.4850(3) 0.83754(12) 0.07425(15) 0.0287(5) Uani 1 1 d . . . H8 H 0.4033 0.7939 0.0865 0.034 Uiso 1 1 calc R . . C9 C 0.3897(3) 0.91772(13) 0.06886(15) 0.0325(5) Uani 1 1 d . . . C10 C 0.2057(3) 0.92032(16) 0.01128(19) 0.0458(6) Uani 1 1 d . . . H10A H 0.1601 0.9751 0.0134 0.069 Uiso 1 1 calc R . . H10B H 0.1347 0.8831 0.0433 0.069 Uiso 1 1 calc R . . H10C H 0.2018 0.9045 -0.0606 0.069 Uiso 1 1 calc R . . C11 C 0.6381(3) 0.83986(13) 0.16611(16) 0.0348(5) Uani 1 1 d . . . H11A H 0.7187 0.8833 0.1545 0.042 Uiso 1 1 calc R . . H11B H 0.5931 0.8535 0.2291 0.042 Uiso 1 1 calc R . . C12 C 0.6657(3) 0.69083(12) 0.20550(14) 0.0259(5) Uani 1 1 d . . . C13 C 0.8115(3) 0.63232(12) 0.21877(14) 0.0247(5) Uani 1 1 d . . . C14 C 0.8145(3) 0.55049(13) 0.23753(16) 0.0346(5) Uani 1 1 d . . . H14 H 0.7121 0.5223 0.2450 0.042 Uiso 1 1 calc R . . C15 C 0.9721(3) 0.51106(14) 0.24508(18) 0.0437(6) Uani 1 1 d . . . H15 H 0.9781 0.4547 0.2577 0.052 Uiso 1 1 calc R . . C16 C 1.1220(3) 0.55275(16) 0.23451(18) 0.0446(6) Uani 1 1 d . . . H16 H 1.2288 0.5243 0.2409 0.054 Uiso 1 1 calc R . . C17 C 1.1188(3) 0.63455(14) 0.21496(17) 0.0368(5) Uani 1 1 d . . . H17 H 1.2208 0.6629 0.2070 0.044 Uiso 1 1 calc R . . C18 C 0.9606(3) 0.67331(12) 0.20745(15) 0.0263(5) Uani 1 1 d . . . C19 C 0.9140(3) 0.75906(13) 0.18597(15) 0.0293(5) Uani 1 1 d . . . Cl1 Cl 0.24102(8) 0.69825(5) -0.06709(6) 0.0591(3) Uani 1 1 d . . . N1 N 0.7354(2) 0.76443(10) 0.18376(12) 0.0262(4) Uani 1 1 d . . . O1 O 0.6825(2) 0.87097(9) -0.04328(12) 0.0363(4) Uani 1 1 d . . . H1 H 0.6576 0.9196 -0.0361 0.054 Uiso 1 1 calc R . . O2 O 0.4614(2) 0.97735(9) 0.11115(13) 0.0435(4) Uani 1 1 d . . . O3 O 0.51493(19) 0.67990(10) 0.21124(12) 0.0410(4) Uani 1 1 d . . . O4 O 1.0071(2) 0.81461(9) 0.17248(13) 0.0454(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 0.0447(13) 0.0376(13) 0.0275(11) -0.0014(9) 0.0058(9) -0.0069(10) C2 0.0737(19) 0.0308(13) 0.0341(12) -0.0050(10) 0.0156(12) -0.0165(12) C3 0.088(2) 0.0267(12) 0.0361(13) -0.0019(10) 0.0256(13) 0.0047(13) C4 0.0584(15) 0.0345(13) 0.0358(12) 0.0000(10) 0.0195(11) 0.0132(12) C5 0.0400(13) 0.0309(12) 0.0276(11) -0.0021(9) 0.0097(9) 0.0024(9) C6 0.0359(12) 0.0261(11) 0.0206(9) -0.0001(8) 0.0054(8) -0.0013(9) C7 0.0299(11) 0.0268(11) 0.0271(10) 0.0033(8) 0.0057(8) 0.0033(9) C8 0.0351(12) 0.0240(11) 0.0271(10) 0.0023(8) 0.0064(9) 0.0066(9) C9 0.0391(13) 0.0324(12) 0.0295(11) 0.0084(9) 0.0153(9) 0.0108(10) C10 0.0407(14) 0.0486(15) 0.0492(14) 0.0118(12) 0.0112(11) 0.0197(12) C11 0.0456(13) 0.0260(11) 0.0305(11) -0.0024(9) 0.0014(9) 0.0104(10) C12 0.0242(11) 0.0312(11) 0.0220(10) 0.0009(8) 0.0038(8) 0.0014(9) C13 0.0266(10) 0.0254(10) 0.0216(9) 0.0004(8) 0.0032(8) 0.0007(8) C14 0.0446(13) 0.0279(11) 0.0315(11) 0.0018(9) 0.0078(9) -0.0044(10) C15 0.0638(17) 0.0290(12) 0.0378(13) 0.0024(10) 0.0085(11) 0.0153(12) C16 0.0466(15) 0.0507(15) 0.0374(12) 0.0016(11) 0.0101(11) 0.0248(12) C17 0.0265(11) 0.0483(14) 0.0359(12) 0.0019(10) 0.0065(9) 0.0058(10) C18 0.0242(10) 0.0299(11) 0.0244(10) 0.0009(8) 0.0035(8) 0.0001(8) C19 0.0302(11) 0.0286(11) 0.0272(10) -0.0008(8) 0.0004(9) -0.0042(9) Cl1 0.0368(4) 0.0670(5) 0.0697(5) -0.0036(3) 0.0004(3) -0.0141(3) N1 0.0287(9) 0.0228(9) 0.0264(9) 0.0007(7) 0.0035(7) 0.0039(7) O1 0.0412(9) 0.0229(8) 0.0477(9) 0.0019(6) 0.0159(7) 0.0004(6) O2 0.0512(10) 0.0285(9) 0.0523(10) 0.0020(7) 0.0139(8) 0.0108(7) O3 0.0239(8) 0.0538(10) 0.0466(9) 0.0133(8) 0.0101(7) 0.0026(7) O4 0.0404(9) 0.0362(9) 0.0560(10) 0.0074(8) 0.0004(8) -0.0158(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 C2 1.388(3) . ? C1 C6 1.397(3) . ? C1 Cl1 1.748(3) . ? C2 C3 1.376(4) . ? C2 H2 0.9500 . ? C3 C4 1.378(4) . ? C3 H3 0.9500 . ? C4 C5 1.393(3) . ? C4 H4 0.9500 . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.519(3) . ? C7 O1 1.417(3) . ? C7 C8 1.564(3) . ? C7 H7 1.0000 . ? C8 C9 1.522(3) . ? C8 C11 1.534(3) . ? C8 H8 1.0000 . ? C9 O2 1.220(3) . ? C9 C10 1.496(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N1 1.462(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O3 1.211(2) . ? C12 N1 1.391(3) . ? C12 C13 1.485(3) . ? C13 C14 1.381(3) . ? C13 C18 1.384(3) . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 C16 1.393(4) . ? C15 H15 0.9500 . ? C16 C17 1.382(4) . ? C16 H16 0.9500 . ? C17 C18 1.383(3) . ? C17 H17 0.9500 . ? C18 C19 1.484(3) . ? C19 O4 1.210(3) . ? C19 N1 1.397(3) . ? O1 H1 0.8400 . ? 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 C6 121.9(2) . . ? C2 C1 Cl1 117.82(19) . . ? C6 C1 Cl1 120.24(18) . . ? C3 C2 C1 119.7(2) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 119.9(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 119.9(2) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 121.7(2) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C6 C1 116.8(2) . . ? C5 C6 C7 121.73(19) . . ? C1 C6 C7 121.4(2) . . ? O1 C7 C6 108.52(16) . . ? O1 C7 C8 110.74(16) . . ? C6 C7 C8 112.42(16) . . ? O1 C7 H7 108.4 . . ? C6 C7 H7 108.4 . . ? C8 C7 H7 108.4 . . ? C9 C8 C11 108.50(17) . . ? C9 C8 C7 108.38(16) . . ? C11 C8 C7 114.25(18) . . ? C9 C8 H8 108.5 . . ? C11 C8 H8 108.5 . . ? C7 C8 H8 108.5 . . ? O2 C9 C10 121.6(2) . . ? O2 C9 C8 120.68(19) . . ? C10 C9 C8 117.7(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C8 114.16(17) . . ? N1 C11 H11A 108.7 . . ? C8 C11 H11A 108.7 . . ? N1 C11 H11B 108.7 . . ? C8 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? O3 C12 N1 124.77(19) . . ? O3 C12 C13 129.20(19) . . ? N1 C12 C13 106.03(16) . . ? C14 C13 C18 121.2(2) . . ? C14 C13 C12 130.6(2) . . ? C18 C13 C12 108.14(17) . . ? C13 C14 C15 117.6(2) . . ? C13 C14 H14 121.2 . . ? C15 C14 H14 121.2 . . ? C14 C15 C16 121.0(2) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 121.4(2) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C18 C17 C16 117.1(2) . . ? C18 C17 H17 121.5 . . ? C16 C17 H17 121.5 . . ? C17 C18 C13 121.7(2) . . ? C17 C18 C19 130.1(2) . . ? C13 C18 C19 108.13(17) . . ? O4 C19 N1 125.27(19) . . ? O4 C19 C18 128.8(2) . . ? N1 C19 C18 105.90(17) . . ? C12 N1 C19 111.75(16) . . ? C12 N1 C11 124.96(17) . . ? C19 N1 C11 123.21(18) . . ? C7 O1 H1 109.5 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.412 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.138