# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Rich Carter' _publ_contact_author_email rich.carter@oregonstate.edu loop_ _publ_author_name M.McIntosh M.Naffziger B.Ashburn L.Zakharov R.Carter data_rc45a _database_code_depnum_ccdc_archive 'CCDC 880837' #TrackingRef 'rc45a(13b).cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 Cl N2 O3' _chemical_formula_weight 356.80 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 Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 13.6753(18) _cell_length_b 8.3473(11) _cell_length_c 15.493(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1768.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1415 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 21.21 _exptl_crystal_description block _exptl_crystal_colour cololress _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9499 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector Bruker apex' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9680 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3413 _reflns_number_gt 2618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0766P)^2^+0.2384P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.22(14) _refine_ls_number_reflns 3413 _refine_ls_number_parameters 244 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1484 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 1.2425(2) 0.6509(4) 1.0797(3) 0.0521(10) Uani 1 1 d . . . O1 O 1.18046(17) 0.7599(3) 1.03637(19) 0.0496(8) Uani 1 1 d . . . Cl1 Cl 1.00544(18) 0.6201(3) 0.89168(13) 0.0557(7) Uani 0.717(6) 1 d PD A 1 C1 C 0.9707(2) 0.8001(4) 0.9436(2) 0.0373(8) Uani 0.50 1 d PD A 1 C1A C 0.9707(2) 0.8001(4) 0.9436(2) 0.0373(8) Uani 0.50 1 d PD A 2 N2A N 0.9907(15) 0.6647(17) 0.8966(12) 0.042(6) Uiso 0.283(6) 1 d PD A 2 O2A O 0.9914(13) 0.538(2) 0.9374(14) 0.114(6) Uiso 0.283(6) 1 d PD A 2 O3A O 0.9937(15) 0.675(3) 0.8187(14) 0.153(9) Uiso 0.283(6) 1 d PD A 2 C2 C 0.9044(2) 0.9019(5) 0.9048(3) 0.0480(11) Uani 1 1 d . . . H2A H 0.8778 0.8762 0.8498 0.058 Uiso 1 1 calc R A 1 C3 C 0.8773(3) 1.0395(5) 0.9457(3) 0.0559(13) Uani 1 1 d . A . H3A H 0.8319 1.1097 0.9188 0.067 Uiso 1 1 calc R . . C4 C 0.9147(3) 1.0782(5) 1.0253(3) 0.0499(11) Uani 1 1 d . . . H4A H 0.8950 1.1736 1.0538 0.060 Uiso 1 1 calc R A 1 N2 N 1.0162(6) 1.0294(9) 1.1488(6) 0.039(2) Uani 0.717(6) 1 d PD A 1 O2 O 1.0834(4) 0.9456(6) 1.1815(3) 0.0699(15) Uani 0.717(6) 1 d PD A 1 O3 O 0.9779(4) 1.1335(5) 1.1843(3) 0.0727(16) Uani 0.717(6) 1 d PD A 1 C5 C 0.9816(2) 0.9761(4) 1.0633(3) 0.0346(8) Uani 0.50 1 d PD A 1 Cl1A Cl 1.0340(8) 1.0136(13) 1.1673(6) 0.058(3) Uiso 0.283(6) 1 d PD A 2 C5A C 0.9816(2) 0.9761(4) 1.0633(3) 0.0346(8) Uani 0.50 1 d PD A 2 C6 C 1.0125(2) 0.8338(4) 1.0232(2) 0.0295(7) Uani 1 1 d . . . C7 C 1.0875(2) 0.7273(4) 1.0613(2) 0.0284(7) Uani 1 1 d . A . C8 C 1.0844(2) 0.6037(4) 1.1154(2) 0.0310(7) Uani 1 1 d . . . C9 C 0.9978(3) 0.5284(6) 1.1562(4) 0.0759(19) Uani 1 1 d . A . H9A H 0.9383 0.5831 1.1367 0.114 Uiso 1 1 calc R . . H9B H 1.0030 0.5373 1.2191 0.114 Uiso 1 1 calc R . . H9C H 0.9946 0.4152 1.1399 0.114 Uiso 1 1 calc R . . C10 C 1.1854(2) 0.5609(4) 1.1265(2) 0.0292(7) Uani 1 1 d . A . C11 C 1.2278(2) 0.4368(4) 1.1838(2) 0.0285(7) Uani 1 1 d . . . C12 C 1.2555(2) 0.4763(4) 1.2674(3) 0.0340(8) Uani 1 1 d . A . C13 C 1.2994(2) 0.3607(4) 1.3191(2) 0.0356(8) Uani 1 1 d . . . H13A H 1.3188 0.3882 1.3761 0.043 Uiso 1 1 calc R A . C14 C 1.3157(2) 0.2056(4) 1.2894(2) 0.0301(7) Uani 1 1 d . A . C15 C 1.2844(2) 0.1681(4) 1.2063(2) 0.0315(7) Uani 1 1 d . . . H15A H 1.2931 0.0619 1.1857 0.038 Uiso 1 1 calc R A . C16 C 1.2410(2) 0.2805(4) 1.1526(2) 0.0282(7) Uani 1 1 d . A . C17 C 1.2393(4) 0.6431(5) 1.3023(3) 0.0590(12) Uani 1 1 d . . . H17A H 1.2084 0.7095 1.2578 0.089 Uiso 1 1 calc R A . H17B H 1.3022 0.6901 1.3186 0.089 Uiso 1 1 calc R . . H17C H 1.1966 0.6378 1.3530 0.089 Uiso 1 1 calc R . . C18 C 1.3655(3) 0.0839(5) 1.3460(3) 0.0433(9) Uani 1 1 d . . . H18A H 1.3705 -0.0182 1.3151 0.065 Uiso 1 1 calc R A . H18B H 1.3273 0.0687 1.3989 0.065 Uiso 1 1 calc R . . H18C H 1.4312 0.1220 1.3609 0.065 Uiso 1 1 calc R . . C19 C 1.2115(3) 0.2362(4) 1.0620(3) 0.0396(8) Uani 1 1 d . . . H19A H 1.2266 0.1231 1.0516 0.059 Uiso 1 1 calc R A . H19B H 1.2476 0.3028 1.0208 0.059 Uiso 1 1 calc R . . H19C H 1.1412 0.2540 1.0547 0.059 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 0.0213(14) 0.0539(19) 0.081(3) 0.0324(18) 0.0004(15) 0.0068(14) O1 0.0250(12) 0.0514(15) 0.072(2) 0.0307(15) 0.0080(12) 0.0035(11) Cl1 0.0636(13) 0.0567(13) 0.0467(11) -0.0140(10) -0.0070(7) 0.0068(11) C1 0.0278(17) 0.0444(19) 0.040(2) 0.0067(18) 0.0044(14) -0.0022(15) C1A 0.0278(17) 0.0444(19) 0.040(2) 0.0067(18) 0.0044(14) -0.0022(15) C2 0.0276(18) 0.071(3) 0.045(3) 0.025(2) -0.0056(16) -0.0061(18) C3 0.030(2) 0.057(3) 0.081(4) 0.038(3) 0.005(2) 0.0086(18) C4 0.040(2) 0.0366(19) 0.073(3) 0.014(2) 0.015(2) 0.0051(17) N2 0.039(4) 0.027(3) 0.051(5) 0.005(3) 0.008(3) 0.006(3) O2 0.080(3) 0.060(3) 0.070(3) -0.020(2) -0.035(3) 0.026(3) O3 0.102(4) 0.049(2) 0.067(3) -0.020(2) 0.013(3) 0.026(2) C5 0.0257(16) 0.0319(17) 0.046(2) 0.0050(16) 0.0058(15) 0.0008(14) C5A 0.0257(16) 0.0319(17) 0.046(2) 0.0050(16) 0.0058(15) 0.0008(14) C6 0.0244(15) 0.0286(15) 0.0356(18) 0.0092(14) 0.0057(14) 0.0011(13) C7 0.0207(14) 0.0295(15) 0.0350(18) 0.0015(15) 0.0016(13) -0.0001(12) C8 0.0196(16) 0.0312(16) 0.042(2) 0.0084(16) 0.0030(13) 0.0048(13) C9 0.035(2) 0.074(3) 0.119(5) 0.066(3) 0.022(3) 0.011(2) C10 0.0251(16) 0.0290(16) 0.0334(19) 0.0014(14) 0.0017(13) -0.0001(13) C11 0.0174(14) 0.0313(15) 0.0367(19) 0.0014(15) 0.0002(12) 0.0027(12) C12 0.0305(17) 0.0301(16) 0.041(2) -0.0038(16) -0.0045(14) 0.0039(14) C13 0.0360(17) 0.0406(19) 0.0302(19) -0.0031(15) -0.0062(14) 0.0027(15) C14 0.0239(15) 0.0358(18) 0.0307(18) 0.0028(15) 0.0007(13) 0.0037(13) C15 0.0245(16) 0.0326(16) 0.037(2) -0.0022(16) 0.0040(13) 0.0043(13) C16 0.0211(14) 0.0330(15) 0.0304(18) -0.0001(15) 0.0007(13) 0.0034(13) C17 0.078(3) 0.037(2) 0.062(3) -0.013(2) -0.024(2) 0.014(2) C18 0.039(2) 0.044(2) 0.048(2) 0.0050(18) -0.0019(17) 0.0147(17) C19 0.0415(19) 0.0408(19) 0.037(2) -0.0024(17) -0.0027(16) 0.0097(15) _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 C10 1.304(4) . ? N1 O1 1.414(4) . ? O1 C7 1.356(4) . ? Cl1 C1 1.769(4) . ? C1 C2 1.381(5) . ? C1 C6 1.387(5) . ? N2A O3A 1.210(17) . ? N2A O2A 1.235(17) . ? C2 C3 1.364(6) . ? C2 H2A 0.9500 . ? C3 C4 1.373(7) . ? C3 H3A 0.9500 . ? C4 C5 1.381(5) . ? C4 H4A 0.9500 . ? N2 O3 1.154(8) . ? N2 O2 1.261(10) . ? N2 C5 1.475(9) . ? C5 C6 1.405(5) . ? C6 C7 1.481(4) . ? C7 C8 1.330(4) . ? C8 C10 1.437(4) . ? C8 C9 1.483(5) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.483(4) . ? C11 C12 1.388(5) . ? C11 C16 1.403(4) . ? C12 C13 1.392(5) . ? C12 C17 1.510(5) . ? C13 C14 1.392(5) . ? C13 H13A 0.9500 . ? C14 C15 1.392(5) . ? C14 C18 1.505(5) . ? C15 C16 1.388(4) . ? C15 H15A 0.9500 . ? C16 C19 1.506(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 O1 106.0(3) . . ? C7 O1 N1 107.3(2) . . ? C2 C1 C6 122.2(3) . . ? C2 C1 Cl1 120.0(3) . . ? C6 C1 Cl1 117.8(3) . . ? O3A N2A O2A 125(2) . . ? C3 C2 C1 119.6(4) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? C2 C3 C4 121.0(4) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C3 C4 C5 119.0(4) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? O3 N2 O2 123.8(8) . . ? O3 N2 C5 120.7(7) . . ? O2 N2 C5 115.3(6) . . ? C4 C5 C6 122.1(4) . . ? C4 C5 N2 114.1(4) . . ? C6 C5 N2 123.8(4) . . ? C1 C6 C5 116.2(3) . . ? C1 C6 C7 121.2(3) . . ? C5 C6 C7 122.6(3) . . ? C8 C7 O1 111.4(3) . . ? C8 C7 C6 134.0(3) . . ? O1 C7 C6 114.5(3) . . ? C7 C8 C10 103.7(3) . . ? C7 C8 C9 128.5(3) . . ? C10 C8 C9 127.7(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 C8 111.5(3) . . ? N1 C10 C11 120.1(3) . . ? C8 C10 C11 128.4(3) . . ? C12 C11 C16 120.5(3) . . ? C12 C11 C10 119.9(3) . . ? C16 C11 C10 119.6(3) . . ? C11 C12 C13 119.4(3) . . ? C11 C12 C17 120.9(3) . . ? C13 C12 C17 119.7(3) . . ? C12 C13 C14 121.5(3) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C13 C14 C15 117.8(3) . . ? C13 C14 C18 120.5(3) . . ? C15 C14 C18 121.8(3) . . ? C16 C15 C14 122.3(3) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C15 C16 C11 118.5(3) . . ? C15 C16 C19 120.5(3) . . ? C11 C16 C19 121.0(3) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C10 N1 O1 C7 0.3(4) . . . . ? C6 C1 C2 C3 -1.0(5) . . . . ? Cl1 C1 C2 C3 179.3(3) . . . . ? C1 C2 C3 C4 -0.2(6) . . . . ? C2 C3 C4 C5 0.7(6) . . . . ? C3 C4 C5 C6 -0.1(5) . . . . ? C3 C4 C5 N2 -179.6(5) . . . . ? O3 N2 C5 C4 11.3(9) . . . . ? O2 N2 C5 C4 -174.2(5) . . . . ? O3 N2 C5 C6 -168.2(6) . . . . ? O2 N2 C5 C6 6.3(9) . . . . ? C2 C1 C6 C5 1.6(5) . . . . ? Cl1 C1 C6 C5 -178.7(2) . . . . ? C2 C1 C6 C7 -176.6(3) . . . . ? Cl1 C1 C6 C7 3.2(4) . . . . ? C4 C5 C6 C1 -1.0(5) . . . . ? N2 C5 C6 C1 178.4(5) . . . . ? C4 C5 C6 C7 177.0(3) . . . . ? N2 C5 C6 C7 -3.5(6) . . . . ? N1 O1 C7 C8 -1.6(4) . . . . ? N1 O1 C7 C6 178.7(3) . . . . ? C1 C6 C7 C8 -92.7(5) . . . . ? C5 C6 C7 C8 89.3(5) . . . . ? C1 C6 C7 O1 87.0(4) . . . . ? C5 C6 C7 O1 -91.0(4) . . . . ? O1 C7 C8 C10 2.0(4) . . . . ? C6 C7 C8 C10 -178.3(4) . . . . ? O1 C7 C8 C9 -178.8(5) . . . . ? C6 C7 C8 C9 0.9(7) . . . . ? O1 N1 C10 C8 0.9(4) . . . . ? O1 N1 C10 C11 -177.3(3) . . . . ? C7 C8 C10 N1 -1.9(4) . . . . ? C9 C8 C10 N1 179.0(5) . . . . ? C7 C8 C10 C11 176.2(3) . . . . ? C9 C8 C10 C11 -2.9(6) . . . . ? N1 C10 C11 C12 87.5(4) . . . . ? C8 C10 C11 C12 -90.4(4) . . . . ? N1 C10 C11 C16 -91.4(4) . . . . ? C8 C10 C11 C16 90.6(4) . . . . ? C16 C11 C12 C13 2.0(5) . . . . ? C10 C11 C12 C13 -177.0(3) . . . . ? C16 C11 C12 C17 -178.5(3) . . . . ? C10 C11 C12 C17 2.6(5) . . . . ? C11 C12 C13 C14 -0.5(5) . . . . ? C17 C12 C13 C14 -180.0(4) . . . . ? C12 C13 C14 C15 -1.5(5) . . . . ? C12 C13 C14 C18 178.6(3) . . . . ? C13 C14 C15 C16 1.9(5) . . . . ? C18 C14 C15 C16 -178.1(3) . . . . ? C14 C15 C16 C11 -0.5(5) . . . . ? C14 C15 C16 C19 177.8(3) . . . . ? C12 C11 C16 C15 -1.6(4) . . . . ? C10 C11 C16 C15 177.4(3) . . . . ? C12 C11 C16 C19 -179.8(3) . . . . ? C10 C11 C16 C19 -0.8(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.253 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.047 # Attachment 'rc46(13d).cif' data_rc46 _database_code_depnum_ccdc_archive 'CCDC 880838' #TrackingRef 'rc46(13d).cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 Br Cl N2 O3' _chemical_formula_weight 421.67 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' Br Br -0.2901 2.4595 '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 7.1538(6) _cell_length_b 8.3848(7) _cell_length_c 15.2827(13) _cell_angle_alpha 78.9380(10) _cell_angle_beta 87.6670(10) _cell_angle_gamma 75.9210(10) _cell_volume 872.63(13) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3126 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 25.04 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 2.528 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5821 _exptl_absorpt_correction_T_max 0.8840 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector Bruker Apex' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9826 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3785 _reflns_number_gt 3270 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.7260P] 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 3785 _refine_ls_number_parameters 243 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1128 _refine_ls_wR_factor_gt 0.1072 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.044 _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 0.55673(4) 0.28513(4) 0.24419(2) 0.03397(13) Uani 1 1 d . . . O1 O 0.0013(3) 0.3204(3) 0.31182(16) 0.0391(6) Uani 1 1 d . . . N1 N -0.0110(4) 0.2999(4) 0.22317(19) 0.0382(7) Uani 1 1 d . . . Cl1 Cl 0.20224(18) 0.66662(14) 0.33710(9) 0.0453(4) Uani 0.854(6) 1 d PD A 1 C1 C 0.2315(5) 0.5068(4) 0.4296(2) 0.0309(7) Uani 0.50 1 d PD A 1 C1A C 0.2315(5) 0.5068(4) 0.4296(2) 0.0309(7) Uani 0.50 1 d PD A 2 N2A N 0.209(4) 0.647(3) 0.3565(14) 0.18(4) Uiso 0.146(6) 1 d PD A 2 O2A O 0.102(3) 0.644(2) 0.2991(12) 0.042(5) Uiso 0.146(6) 1 d PD A 2 O3A O 0.301(4) 0.750(4) 0.358(2) 0.099(10) Uiso 0.146(6) 1 d PD A 2 C2 C 0.2614(5) 0.5413(5) 0.5123(2) 0.0366(8) Uani 1 1 d . . . H2A H 0.2644 0.6515 0.5181 0.044 Uiso 1 1 calc R A 1 C3 C 0.2867(5) 0.4151(5) 0.5857(2) 0.0392(8) Uani 1 1 d . A . H3A H 0.3070 0.4381 0.6426 0.047 Uiso 1 1 calc R . . C4 C 0.2827(5) 0.2544(5) 0.5775(2) 0.0382(8) Uani 1 1 d . . . H4A H 0.3014 0.1668 0.6283 0.046 Uiso 1 1 calc R A 1 C5 C 0.2514(5) 0.2233(4) 0.4947(2) 0.0324(7) Uani 0.50 1 d PD A 1 O2 O 0.2743(11) 0.0051(5) 0.4228(4) 0.120(3) Uani 0.854(6) 1 d PD A 1 O3 O 0.2288(12) -0.0426(6) 0.5546(3) 0.141(3) Uani 0.854(6) 1 d PD A 1 N2 N 0.2407(11) 0.0479(8) 0.4901(5) 0.0372(15) Uani 0.854(6) 1 d PD A 1 C5A C 0.2514(5) 0.2233(4) 0.4947(2) 0.0324(7) Uani 0.50 1 d PD A 2 Cl1A Cl 0.272(2) 0.0212(18) 0.4783(13) 0.051(4) Uiso 0.146(6) 1 d PD A 2 C6 C 0.2256(4) 0.3469(4) 0.4178(2) 0.0281(6) Uani 1 1 d . . . C7 C 0.1856(5) 0.3184(4) 0.3294(2) 0.0292(7) Uani 1 1 d . A . C8 C 0.2926(4) 0.2977(4) 0.2562(2) 0.0275(6) Uani 1 1 d . . . C9 C 0.1640(4) 0.2868(4) 0.1903(2) 0.0280(6) Uani 1 1 d . A . C10 C 0.2041(4) 0.2612(4) 0.0975(2) 0.0277(6) Uani 1 1 d . . . C11 C 0.2055(5) 0.1056(4) 0.0761(2) 0.0335(7) Uani 1 1 d . A . C12 C 0.2437(5) 0.0831(4) -0.0110(2) 0.0377(8) Uani 1 1 d . . . H12A H 0.2468 -0.0226 -0.0257 0.045 Uiso 1 1 calc R A . C13 C 0.2775(5) 0.2111(5) -0.0771(2) 0.0377(8) Uani 1 1 d . A . C14 C 0.2762(5) 0.3633(4) -0.0544(2) 0.0350(7) Uani 1 1 d . . . H14A H 0.3005 0.4513 -0.0992 0.042 Uiso 1 1 calc R A . C15 C 0.2403(4) 0.3912(4) 0.0320(2) 0.0296(7) Uani 1 1 d . A . C16 C 0.1667(7) -0.0370(5) 0.1462(3) 0.0490(10) Uani 1 1 d . . . H16A H 0.1736 -0.1349 0.1189 0.073 Uiso 1 1 calc R A . H16B H 0.0379 -0.0027 0.1711 0.073 Uiso 1 1 calc R . . H16D H 0.2633 -0.0655 0.1939 0.073 Uiso 1 1 calc R . . C17 C 0.3091(7) 0.1884(6) -0.1731(3) 0.0590(12) Uani 1 1 d . . . H17A H 0.3307 0.2917 -0.2097 0.088 Uiso 1 1 calc R A . H17C H 0.1951 0.1627 -0.1951 0.088 Uiso 1 1 calc R . . H17B H 0.4218 0.0961 -0.1764 0.088 Uiso 1 1 calc R . . C18 C 0.2374(5) 0.5606(4) 0.0528(3) 0.0381(8) Uani 1 1 d . . . H18A H 0.2663 0.6342 -0.0013 0.057 Uiso 1 1 calc R A . H18B H 0.3344 0.5481 0.0987 0.057 Uiso 1 1 calc R . . H18C H 0.1096 0.6095 0.0746 0.057 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 Br1 0.02594(18) 0.0479(2) 0.03074(19) -0.01027(14) 0.00103(12) -0.01180(14) O1 0.0303(12) 0.0626(16) 0.0317(13) -0.0177(12) 0.0058(10) -0.0193(11) N1 0.0345(15) 0.0565(19) 0.0297(15) -0.0156(13) -0.0009(12) -0.0168(14) Cl1 0.0615(8) 0.0336(6) 0.0414(7) 0.0017(5) -0.0024(5) -0.0190(5) C1 0.0318(17) 0.0303(17) 0.0300(17) -0.0027(13) 0.0022(13) -0.0093(13) C1A 0.0318(17) 0.0303(17) 0.0300(17) -0.0027(13) 0.0022(13) -0.0093(13) C2 0.0394(19) 0.0368(19) 0.0380(19) -0.0162(15) 0.0039(15) -0.0109(15) C3 0.0377(19) 0.053(2) 0.0292(18) -0.0159(16) 0.0012(14) -0.0090(16) C4 0.0409(19) 0.045(2) 0.0248(17) -0.0024(15) 0.0004(14) -0.0071(16) C5 0.0315(17) 0.0313(17) 0.0327(17) -0.0050(14) 0.0027(13) -0.0054(13) O2 0.265(8) 0.046(2) 0.062(3) -0.019(2) 0.013(4) -0.057(4) O3 0.325(10) 0.057(3) 0.054(3) 0.013(2) -0.041(4) -0.085(4) N2 0.046(3) 0.027(3) 0.033(3) 0.000(2) 0.003(2) -0.003(2) C5A 0.0315(17) 0.0313(17) 0.0327(17) -0.0050(14) 0.0027(13) -0.0054(13) C6 0.0270(15) 0.0333(17) 0.0241(15) -0.0055(12) 0.0044(12) -0.0080(13) C7 0.0282(16) 0.0336(17) 0.0280(16) -0.0066(13) 0.0008(12) -0.0111(13) C8 0.0252(15) 0.0318(17) 0.0267(15) -0.0054(13) 0.0007(12) -0.0093(13) C9 0.0286(16) 0.0288(16) 0.0285(16) -0.0059(13) 0.0005(12) -0.0103(13) C10 0.0271(15) 0.0323(17) 0.0249(15) -0.0039(13) -0.0026(12) -0.0102(13) C11 0.0425(19) 0.0310(17) 0.0274(16) -0.0015(13) -0.0068(14) -0.0112(14) C12 0.047(2) 0.0336(18) 0.0337(18) -0.0113(14) -0.0065(15) -0.0069(15) C13 0.0323(18) 0.050(2) 0.0285(17) -0.0097(15) 0.0009(14) -0.0045(15) C14 0.0316(17) 0.0411(19) 0.0296(17) 0.0041(14) -0.0008(13) -0.0119(14) C15 0.0245(15) 0.0301(17) 0.0341(17) -0.0022(13) -0.0046(13) -0.0088(13) C16 0.078(3) 0.035(2) 0.037(2) 0.0018(16) -0.0094(19) -0.025(2) C17 0.066(3) 0.078(3) 0.035(2) -0.020(2) 0.009(2) -0.016(2) C18 0.0376(19) 0.0298(17) 0.048(2) -0.0031(15) -0.0050(16) -0.0129(15) _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 C8 1.870(3) . ? O1 C7 1.352(4) . ? O1 N1 1.407(3) . ? N1 C9 1.317(4) . ? Cl1 C1 1.732(3) . ? C1 C2 1.386(5) . ? C1 C6 1.397(5) . ? N2A O2A 1.199(19) . ? N2A O3A 1.201(19) . ? C2 C3 1.370(5) . ? C2 H2A 0.9500 . ? C3 C4 1.384(5) . ? C3 H3A 0.9500 . ? C4 C5 1.377(5) . ? C4 H4A 0.9500 . ? C5 C6 1.396(4) . ? C5 N2 1.506(7) . ? O2 N2 1.150(8) . ? O3 N2 1.138(8) . ? C6 C7 1.467(4) . ? C7 C8 1.344(4) . ? C8 C9 1.422(4) . ? C9 C10 1.481(4) . ? C10 C15 1.398(4) . ? C10 C11 1.402(4) . ? C11 C12 1.388(5) . ? C11 C16 1.516(5) . ? C12 C13 1.386(5) . ? C12 H12A 0.9500 . ? C13 C14 1.384(5) . ? C13 C17 1.515(5) . ? C14 C15 1.388(5) . ? C14 H14A 0.9500 . ? C15 C18 1.509(5) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16D 0.9800 . ? C17 H17A 0.9800 . ? C17 H17C 0.9800 . ? C17 H17B 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 C7 O1 N1 108.7(2) . . ? C9 N1 O1 106.2(3) . . ? C2 C1 C6 122.4(3) . . ? C2 C1 Cl1 119.1(3) . . ? C6 C1 Cl1 118.5(2) . . ? O2A N2A O3A 128(2) . . ? C3 C2 C1 119.4(3) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C4 120.5(3) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 119.1(3) . . ? C5 C4 H4A 120.4 . . ? C3 C4 H4A 120.4 . . ? C4 C5 C6 122.8(3) . . ? C4 C5 N2 117.0(4) . . ? C6 C5 N2 120.2(4) . . ? O2 N2 O3 122.6(7) . . ? O2 N2 C5 117.5(5) . . ? O3 N2 C5 118.8(6) . . ? C5 C6 C1 115.8(3) . . ? C5 C6 C7 123.9(3) . . ? C1 C6 C7 120.3(3) . . ? C8 C7 O1 109.2(3) . . ? C8 C7 C6 133.9(3) . . ? O1 C7 C6 116.8(3) . . ? C7 C8 C9 105.9(3) . . ? C7 C8 Br1 126.8(2) . . ? C9 C8 Br1 127.3(2) . . ? N1 C9 C8 110.0(3) . . ? N1 C9 C10 120.7(3) . . ? C8 C9 C10 129.3(3) . . ? C15 C10 C11 120.5(3) . . ? C15 C10 C9 120.1(3) . . ? C11 C10 C9 119.4(3) . . ? C12 C11 C10 118.8(3) . . ? C12 C11 C16 119.9(3) . . ? C10 C11 C16 121.2(3) . . ? C13 C12 C11 121.6(3) . . ? C13 C12 H12A 119.2 . . ? C11 C12 H12A 119.2 . . ? C14 C13 C12 118.5(3) . . ? C14 C13 C17 120.1(3) . . ? C12 C13 C17 121.3(4) . . ? C13 C14 C15 121.9(3) . . ? C13 C14 H14A 119.0 . . ? C15 C14 H14A 119.0 . . ? C14 C15 C10 118.6(3) . . ? C14 C15 C18 119.7(3) . . ? C10 C15 C18 121.7(3) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16D 109.5 . . ? H16A C16 H16D 109.5 . . ? H16B C16 H16D 109.5 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? H17C C17 H17B 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 O1 N1 C9 -0.2(4) . . . . ? C6 C1 C2 C3 0.1(5) . . . . ? Cl1 C1 C2 C3 -179.4(3) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? C2 C3 C4 C5 -0.6(5) . . . . ? C3 C4 C5 C6 0.8(5) . . . . ? C3 C4 C5 N2 -177.7(4) . . . . ? C4 C5 N2 O2 -156.5(7) . . . . ? C6 C5 N2 O2 25.0(9) . . . . ? C4 C5 N2 O3 12.0(9) . . . . ? C6 C5 N2 O3 -166.6(7) . . . . ? C4 C5 C6 C1 -0.6(5) . . . . ? N2 C5 C6 C1 177.8(4) . . . . ? C4 C5 C6 C7 -177.9(3) . . . . ? N2 C5 C6 C7 0.6(6) . . . . ? C2 C1 C6 C5 0.1(5) . . . . ? Cl1 C1 C6 C5 179.6(2) . . . . ? C2 C1 C6 C7 177.5(3) . . . . ? Cl1 C1 C6 C7 -3.1(4) . . . . ? N1 O1 C7 C8 0.0(4) . . . . ? N1 O1 C7 C6 176.9(3) . . . . ? C5 C6 C7 C8 -103.3(5) . . . . ? C1 C6 C7 C8 79.6(5) . . . . ? C5 C6 C7 O1 80.8(4) . . . . ? C1 C6 C7 O1 -96.3(4) . . . . ? O1 C7 C8 C9 0.1(4) . . . . ? C6 C7 C8 C9 -176.0(4) . . . . ? O1 C7 C8 Br1 -179.7(2) . . . . ? C6 C7 C8 Br1 4.1(6) . . . . ? O1 N1 C9 C8 0.2(4) . . . . ? O1 N1 C9 C10 179.1(3) . . . . ? C7 C8 C9 N1 -0.2(4) . . . . ? Br1 C8 C9 N1 179.6(2) . . . . ? C7 C8 C9 C10 -179.0(3) . . . . ? Br1 C8 C9 C10 0.8(5) . . . . ? N1 C9 C10 C15 107.9(4) . . . . ? C8 C9 C10 C15 -73.5(5) . . . . ? N1 C9 C10 C11 -72.2(4) . . . . ? C8 C9 C10 C11 106.5(4) . . . . ? C15 C10 C11 C12 0.1(5) . . . . ? C9 C10 C11 C12 -179.9(3) . . . . ? C15 C10 C11 C16 180.0(3) . . . . ? C9 C10 C11 C16 0.0(5) . . . . ? C10 C11 C12 C13 -0.9(5) . . . . ? C16 C11 C12 C13 179.2(4) . . . . ? C11 C12 C13 C14 1.2(5) . . . . ? C11 C12 C13 C17 -176.8(4) . . . . ? C12 C13 C14 C15 -0.6(5) . . . . ? C17 C13 C14 C15 177.4(3) . . . . ? C13 C14 C15 C10 -0.2(5) . . . . ? C13 C14 C15 C18 -179.0(3) . . . . ? C11 C10 C15 C14 0.5(5) . . . . ? C9 C10 C15 C14 -179.6(3) . . . . ? C11 C10 C15 C18 179.2(3) . . . . ? C9 C10 C15 C18 -0.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.696 _refine_diff_density_min -0.598 _refine_diff_density_rms 0.088 # Attachment 'rc63(13h).cif' data_rc63 _database_code_depnum_ccdc_archive 'CCDC 880839' #TrackingRef 'rc63(13h).cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 N2 O3' _chemical_formula_weight 308.33 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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 19.125(5) _cell_length_b 7.3751(19) _cell_length_c 22.492(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3172.5(14) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5456 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 22.87 _exptl_crystal_description prizm _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9669 _exptl_absorpt_correction_T_max 0.9894 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22732 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5589 _reflns_number_gt 4950 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1030P)^2^+0.1702P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(13) _refine_ls_number_reflns 5589 _refine_ls_number_parameters 416 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1442 _refine_ls_wR_factor_gt 0.1346 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.34585(14) 0.6597(3) 0.42318(15) 0.0726(8) Uani 1 1 d . . . O2 O 0.28050(14) 0.4571(3) 0.46298(12) 0.0679(7) Uani 1 1 d . . . O3 O 0.22323(9) 0.2317(3) 0.37322(11) 0.0477(5) Uani 1 1 d . . . N1 N 0.32960(12) 0.5029(3) 0.43240(12) 0.0421(6) Uani 1 1 d . . . N2 N 0.15658(11) 0.1650(4) 0.38973(14) 0.0507(7) Uani 1 1 d . . . C1 C 0.37279(12) 0.3605(4) 0.40386(12) 0.0324(6) Uani 1 1 d . . . C2 C 0.44108(14) 0.4049(4) 0.39128(14) 0.0396(7) Uani 1 1 d . . . H2A H 0.4582 0.5229 0.3999 0.048 Uiso 1 1 calc R . . C3 C 0.48454(14) 0.2768(5) 0.36602(15) 0.0464(8) Uani 1 1 d . . . H3A H 0.5317 0.3059 0.3567 0.056 Uiso 1 1 calc R . . C4 C 0.45850(14) 0.1058(5) 0.35456(14) 0.0431(7) Uani 1 1 d . . . H4A H 0.4880 0.0171 0.3369 0.052 Uiso 1 1 calc R . . C5 C 0.38962(14) 0.0613(4) 0.36848(13) 0.0368(6) Uani 1 1 d . . . H5A H 0.3729 -0.0578 0.3610 0.044 Uiso 1 1 calc R . . C6 C 0.34509(12) 0.1898(4) 0.39321(11) 0.0295(6) Uani 1 1 d . . . C7 C 0.27137(13) 0.1387(4) 0.40407(12) 0.0314(6) Uani 1 1 d . . . C8 C 0.24060(13) 0.0150(4) 0.43883(13) 0.0330(6) Uani 1 1 d . . . H8A H 0.2626 -0.0695 0.4647 0.040 Uiso 1 1 calc R . . C9 C 0.16792(13) 0.0378(4) 0.42865(12) 0.0319(6) Uani 1 1 d . . . C10 C 0.10730(12) -0.0566(3) 0.45720(12) 0.0308(6) Uani 1 1 d . . . C11 C 0.08971(12) -0.2328(3) 0.43983(12) 0.0304(6) Uani 1 1 d . . . C12 C 0.03428(14) -0.3183(4) 0.46741(12) 0.0355(6) Uani 1 1 d . . . H12B H 0.0219 -0.4374 0.4553 0.043 Uiso 1 1 calc R . . C13 C -0.00385(13) -0.2358(4) 0.51225(14) 0.0366(7) Uani 1 1 d . . . C14 C 0.01388(14) -0.0609(4) 0.52909(13) 0.0374(6) Uani 1 1 d . . . H14B H -0.0124 -0.0023 0.5594 0.045 Uiso 1 1 calc R . . C15 C 0.06966(14) 0.0311(4) 0.50242(12) 0.0337(6) Uani 1 1 d . . . C16 C 0.12942(14) -0.3293(4) 0.39037(14) 0.0435(7) Uani 1 1 d . . . H16D H 0.1099 -0.4508 0.3846 0.065 Uiso 1 1 calc R . . H16E H 0.1789 -0.3391 0.4013 0.065 Uiso 1 1 calc R . . H16F H 0.1250 -0.2599 0.3534 0.065 Uiso 1 1 calc R . . C17 C -0.06358(16) -0.3350(5) 0.54240(16) 0.0529(8) Uani 1 1 d . . . H17D H -0.0687 -0.4559 0.5248 0.079 Uiso 1 1 calc R . . H17E H -0.1070 -0.2665 0.5369 0.079 Uiso 1 1 calc R . . H17F H -0.0537 -0.3466 0.5850 0.079 Uiso 1 1 calc R . . C18 C 0.09021(17) 0.2170(4) 0.52353(17) 0.0530(8) Uani 1 1 d . . . H18D H 0.0583 0.2560 0.5551 0.079 Uiso 1 1 calc R . . H18E H 0.0876 0.3026 0.4903 0.079 Uiso 1 1 calc R . . H18F H 0.1381 0.2137 0.5390 0.079 Uiso 1 1 calc R . . O1' O -0.10339(12) 0.3400(3) 0.21307(12) 0.0553(6) Uani 1 1 d . . . O2' O -0.05499(13) 0.5413(3) 0.15715(11) 0.0590(6) Uani 1 1 d . . . O3' O 0.01482(9) 0.7416(3) 0.24956(11) 0.0488(6) Uani 1 1 d . . . N1' N -0.09470(12) 0.4963(3) 0.19698(11) 0.0366(5) Uani 1 1 d . . . N2' N 0.08183(11) 0.8013(3) 0.23231(14) 0.0516(7) Uani 1 1 d . . . C1' C -0.13591(12) 0.6378(3) 0.22675(12) 0.0296(6) Uani 1 1 d . . . C2' C -0.20386(13) 0.5925(4) 0.24241(13) 0.0355(6) Uani 1 1 d . . . H2'A H -0.2215 0.4739 0.2358 0.043 Uiso 1 1 calc R . . C3' C -0.24544(12) 0.7263(4) 0.26818(14) 0.0397(7) Uani 1 1 d . . . H3'A H -0.2925 0.7001 0.2786 0.048 Uiso 1 1 calc R . . C4' C -0.21864(13) 0.8950(4) 0.27841(13) 0.0402(7) Uani 1 1 d . . . H4'A H -0.2474 0.9850 0.2962 0.048 Uiso 1 1 calc R . . C5' C -0.15045(14) 0.9373(4) 0.26333(13) 0.0342(6) Uani 1 1 d . . . H5'A H -0.1329 1.0555 0.2711 0.041 Uiso 1 1 calc R . . C6' C -0.10740(12) 0.8088(3) 0.23700(12) 0.0293(6) Uani 1 1 d . . . C7' C -0.03343(13) 0.8527(3) 0.22505(12) 0.0302(5) Uani 1 1 d . . . C8' C -0.00174(14) 0.9840(4) 0.19379(13) 0.0311(6) Uani 1 1 d . . . H8'A H -0.0230 1.0809 0.1726 0.037 Uiso 1 1 calc R . . C9' C 0.07121(13) 0.9452(3) 0.19949(12) 0.0307(6) Uani 1 1 d . . . C10' C 0.13208(13) 1.0402(3) 0.17242(12) 0.0304(6) Uani 1 1 d . . . C11' C 0.14904(13) 1.2157(4) 0.19115(13) 0.0323(6) Uani 1 1 d . . . C12' C 0.20705(14) 1.3002(4) 0.16535(13) 0.0379(6) Uani 1 1 d . . . H12A H 0.2193 1.4186 0.1783 0.046 Uiso 1 1 calc R . . C13' C 0.24719(14) 1.2192(5) 0.12185(14) 0.0426(7) Uani 1 1 d . . . C14' C 0.22857(16) 1.0462(4) 0.10387(14) 0.0439(7) Uani 1 1 d . . . H14A H 0.2558 0.9881 0.0741 0.053 Uiso 1 1 calc R . . C15' C 0.17119(14) 0.9533(4) 0.12788(13) 0.0386(6) Uani 1 1 d . . . C16' C 0.10788(15) 1.3108(4) 0.23801(14) 0.0430(7) Uani 1 1 d . . . H16A H 0.1280 1.4312 0.2450 0.065 Uiso 1 1 calc R . . H16B H 0.1093 1.2402 0.2749 0.065 Uiso 1 1 calc R . . H16C H 0.0593 1.3237 0.2249 0.065 Uiso 1 1 calc R . . C17' C 0.30891(17) 1.3149(6) 0.09409(17) 0.0624(10) Uani 1 1 d . . . H17A H 0.3142 1.4351 0.1121 0.094 Uiso 1 1 calc R . . H17B H 0.3011 1.3279 0.0512 0.094 Uiso 1 1 calc R . . H17C H 0.3514 1.2438 0.1009 0.094 Uiso 1 1 calc R . . C18' C 0.15297(18) 0.7670(4) 0.10433(19) 0.0572(9) Uani 1 1 d . . . H18A H 0.1119 0.7204 0.1255 0.086 Uiso 1 1 calc R . . H18B H 0.1926 0.6848 0.1105 0.086 Uiso 1 1 calc R . . H18C H 0.1426 0.7751 0.0617 0.086 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 0.0708(16) 0.0375(13) 0.109(2) -0.0060(13) 0.0068(16) 0.0037(11) O2 0.0658(16) 0.0623(15) 0.0755(18) -0.0130(13) 0.0372(15) 0.0056(12) O3 0.0260(9) 0.0616(13) 0.0554(13) 0.0313(11) -0.0031(9) -0.0052(9) N1 0.0403(14) 0.0424(14) 0.0436(15) -0.0075(11) -0.0049(12) 0.0033(11) N2 0.0209(11) 0.0667(17) 0.0644(17) 0.0351(14) -0.0031(11) -0.0056(11) C1 0.0271(13) 0.0420(15) 0.0281(14) 0.0005(12) -0.0038(11) 0.0062(11) C2 0.0325(14) 0.0453(16) 0.0409(16) -0.0021(13) -0.0083(13) -0.0090(12) C3 0.0231(13) 0.077(2) 0.0389(17) -0.0072(16) -0.0008(12) -0.0057(15) C4 0.0284(14) 0.0567(19) 0.0444(18) -0.0105(14) -0.0036(13) 0.0090(13) C5 0.0319(14) 0.0423(15) 0.0361(15) -0.0032(13) -0.0021(12) 0.0028(12) C6 0.0246(12) 0.0387(14) 0.0251(13) 0.0048(11) -0.0029(10) -0.0018(11) C7 0.0241(12) 0.0384(14) 0.0318(14) 0.0041(11) -0.0034(11) 0.0019(10) C8 0.0225(12) 0.0395(14) 0.0370(15) 0.0087(12) -0.0026(11) 0.0028(11) C9 0.0239(13) 0.0367(14) 0.0352(15) 0.0048(12) -0.0007(11) -0.0005(10) C10 0.0235(12) 0.0365(14) 0.0325(14) 0.0095(11) -0.0015(11) 0.0037(10) C11 0.0261(11) 0.0389(14) 0.0262(14) 0.0022(11) -0.0006(11) 0.0040(11) C12 0.0327(14) 0.0361(14) 0.0378(16) 0.0051(13) -0.0002(12) -0.0006(11) C13 0.0300(14) 0.0469(16) 0.0328(16) 0.0116(12) 0.0021(11) -0.0011(11) C14 0.0308(14) 0.0502(17) 0.0312(15) 0.0053(12) 0.0054(12) 0.0107(12) C15 0.0327(14) 0.0358(14) 0.0325(14) 0.0041(11) 0.0001(11) 0.0066(11) C16 0.0380(16) 0.0474(17) 0.0452(17) -0.0033(14) 0.0118(14) 0.0014(12) C17 0.0405(16) 0.065(2) 0.054(2) 0.0159(17) 0.0137(14) -0.0027(15) C18 0.0556(19) 0.0438(17) 0.060(2) -0.0078(16) 0.0006(17) 0.0087(15) O1' 0.0572(14) 0.0323(11) 0.0765(17) 0.0005(10) 0.0050(12) 0.0053(9) O2' 0.0625(15) 0.0540(13) 0.0605(15) -0.0019(12) 0.0285(13) 0.0090(11) O3' 0.0240(9) 0.0491(12) 0.0732(16) 0.0334(11) -0.0049(9) -0.0038(8) N1' 0.0334(12) 0.0336(12) 0.0427(14) -0.0033(10) -0.0004(11) 0.0043(10) N2' 0.0203(11) 0.0522(15) 0.083(2) 0.0334(15) 0.0007(12) -0.0042(10) C1' 0.0231(12) 0.0349(13) 0.0307(14) 0.0012(12) -0.0014(10) 0.0012(10) C2' 0.0265(12) 0.0398(14) 0.0401(15) -0.0062(13) -0.0021(12) -0.0101(11) C3' 0.0192(12) 0.0592(19) 0.0407(17) -0.0062(14) 0.0023(11) -0.0009(12) C4' 0.0291(14) 0.0533(18) 0.0382(16) -0.0096(13) 0.0007(13) 0.0104(12) C5' 0.0350(14) 0.0318(14) 0.0358(15) -0.0018(12) -0.0012(12) 0.0001(11) C6' 0.0226(12) 0.0370(14) 0.0283(14) 0.0019(12) -0.0028(10) -0.0029(10) C7' 0.0252(12) 0.0315(12) 0.0339(14) 0.0048(11) -0.0022(11) 0.0023(10) C8' 0.0281(12) 0.0296(12) 0.0357(15) 0.0059(11) 0.0037(11) 0.0030(10) C9' 0.0256(13) 0.0311(12) 0.0354(14) 0.0086(12) -0.0010(11) -0.0008(10) C10' 0.0221(12) 0.0342(13) 0.0349(14) 0.0097(11) -0.0001(10) 0.0006(10) C11' 0.0275(13) 0.0364(13) 0.0330(14) 0.0098(12) -0.0014(11) 0.0011(11) C12' 0.0331(14) 0.0422(15) 0.0384(16) 0.0120(13) -0.0050(12) -0.0100(11) C13' 0.0310(14) 0.0635(19) 0.0332(16) 0.0158(14) 0.0000(12) -0.0006(13) C14' 0.0390(16) 0.0601(19) 0.0327(15) 0.0050(14) 0.0070(12) 0.0059(13) C15' 0.0348(15) 0.0426(15) 0.0383(15) 0.0055(13) 0.0024(12) 0.0030(12) C16' 0.0403(15) 0.0455(16) 0.0433(17) -0.0023(14) 0.0009(13) 0.0012(12) C17' 0.0440(17) 0.089(3) 0.054(2) 0.027(2) 0.0044(16) -0.0140(18) C18' 0.068(2) 0.0441(17) 0.060(2) -0.0033(16) 0.0072(18) 0.0044(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 O1 N1 1.215(3) . ? O2 N1 1.212(3) . ? O3 C7 1.341(3) . ? O3 N2 1.416(3) . ? N1 C1 1.482(4) . ? N2 C9 1.302(4) . ? C1 C2 1.376(4) . ? C1 C6 1.387(4) . ? C2 C3 1.381(4) . ? C2 H2A 0.9500 . ? C3 C4 1.380(5) . ? C3 H3A 0.9500 . ? C4 C5 1.393(4) . ? C4 H4A 0.9500 . ? C5 C6 1.390(4) . ? C5 H5A 0.9500 . ? C6 C7 1.480(3) . ? C7 C8 1.338(4) . ? C8 C9 1.419(4) . ? C8 H8A 0.9500 . ? C9 C10 1.497(3) . ? C10 C11 1.398(4) . ? C10 C15 1.404(4) . ? C11 C12 1.381(4) . ? C11 C16 1.523(4) . ? C12 C13 1.385(4) . ? C12 H12B 0.9500 . ? C13 C14 1.387(4) . ? C13 C17 1.516(4) . ? C14 C15 1.399(4) . ? C14 H14B 0.9500 . ? C15 C18 1.504(4) . ? C16 H16D 0.9800 . ? C16 H16E 0.9800 . ? C16 H16F 0.9800 . ? C17 H17D 0.9800 . ? C17 H17E 0.9800 . ? C17 H17F 0.9800 . ? C18 H18D 0.9800 . ? C18 H18E 0.9800 . ? C18 H18F 0.9800 . ? O1' N1' 1.220(3) . ? O2' N1' 1.220(3) . ? O3' C7' 1.351(3) . ? O3' N2' 1.410(3) . ? N1' C1' 1.469(3) . ? N2' C9' 1.308(3) . ? C1' C2' 1.387(4) . ? C1' C6' 1.393(3) . ? C2' C3' 1.393(4) . ? C2' H2'A 0.9500 . ? C3' C4' 1.365(4) . ? C3' H3'A 0.9500 . ? C4' C5' 1.383(4) . ? C4' H4'A 0.9500 . ? C5' C6' 1.388(4) . ? C5' H5'A 0.9500 . ? C6' C7' 1.476(3) . ? C7' C8' 1.342(4) . ? C8' C9' 1.430(4) . ? C8' H8'A 0.9500 . ? C9' C10' 1.489(4) . ? C10' C15' 1.405(4) . ? C10' C11' 1.399(4) . ? C11' C12' 1.399(4) . ? C11' C16' 1.491(4) . ? C12' C13' 1.380(5) . ? C12' H12A 0.9500 . ? C13' C14' 1.385(5) . ? C13' C17' 1.511(4) . ? C14' C15' 1.402(4) . ? C14' H14A 0.9500 . ? C15' C18' 1.513(4) . ? C16' H16A 0.9800 . ? C16' H16B 0.9800 . ? C16' H16C 0.9800 . ? C17' H17A 0.9800 . ? C17' H17B 0.9800 . ? C17' H17C 0.9800 . ? C18' H18A 0.9800 . ? C18' H18B 0.9800 . ? C18' H18C 0.9800 . ? 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 C7 O3 N2 107.7(2) . . ? O2 N1 O1 124.1(3) . . ? O2 N1 C1 118.7(3) . . ? O1 N1 C1 117.2(3) . . ? C9 N2 O3 106.1(2) . . ? C2 C1 C6 122.9(2) . . ? C2 C1 N1 116.7(3) . . ? C6 C1 N1 120.3(2) . . ? C1 C2 C3 119.5(3) . . ? C1 C2 H2A 120.2 . . ? C3 C2 H2A 120.2 . . ? C4 C3 C2 119.0(3) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 120.9(3) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C1 C6 C5 117.0(2) . . ? C1 C6 C7 124.5(2) . . ? C5 C6 C7 118.4(2) . . ? C8 C7 O3 110.4(2) . . ? C8 C7 C6 133.6(2) . . ? O3 C7 C6 116.0(2) . . ? C7 C8 C9 104.8(2) . . ? C7 C8 H8A 127.6 . . ? C9 C8 H8A 127.6 . . ? N2 C9 C8 110.9(2) . . ? N2 C9 C10 119.7(2) . . ? C8 C9 C10 129.4(2) . . ? C11 C10 C15 120.5(2) . . ? C11 C10 C9 119.9(2) . . ? C15 C10 C9 119.6(2) . . ? C12 C11 C10 118.9(2) . . ? C12 C11 C16 119.9(2) . . ? C10 C11 C16 121.2(2) . . ? C13 C12 C11 122.1(3) . . ? C13 C12 H12B 119.0 . . ? C11 C12 H12B 119.0 . . ? C12 C13 C14 118.6(2) . . ? C12 C13 C17 120.7(3) . . ? C14 C13 C17 120.7(3) . . ? C13 C14 C15 121.4(3) . . ? C13 C14 H14B 119.3 . . ? C15 C14 H14B 119.3 . . ? C14 C15 C10 118.6(2) . . ? C14 C15 C18 120.4(3) . . ? C10 C15 C18 121.0(3) . . ? C11 C16 H16D 109.5 . . ? C11 C16 H16E 109.5 . . ? H16D C16 H16E 109.5 . . ? C11 C16 H16F 109.5 . . ? H16D C16 H16F 109.5 . . ? H16E C16 H16F 109.5 . . ? C13 C17 H17D 109.5 . . ? C13 C17 H17E 109.5 . . ? H17D C17 H17E 109.5 . . ? C13 C17 H17F 109.5 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? C15 C18 H18D 109.5 . . ? C15 C18 H18E 109.5 . . ? H18D C18 H18E 109.5 . . ? C15 C18 H18F 109.5 . . ? H18D C18 H18F 109.5 . . ? H18E C18 H18F 109.5 . . ? C7' O3' N2' 108.61(19) . . ? O2' N1' O1' 124.0(2) . . ? O2' N1' C1' 118.4(2) . . ? O1' N1' C1' 117.6(2) . . ? C9' N2' O3' 105.52(19) . . ? C2' C1' C6' 122.9(2) . . ? C2' C1' N1' 116.6(2) . . ? C6' C1' N1' 120.5(2) . . ? C1' C2' C3' 118.0(2) . . ? C1' C2' H2'A 121.0 . . ? C3' C2' H2'A 121.0 . . ? C4' C3' C2' 120.1(2) . . ? C4' C3' H3'A 120.0 . . ? C2' C3' H3'A 120.0 . . ? C3' C4' C5' 121.2(3) . . ? C3' C4' H4'A 119.4 . . ? C5' C4' H4'A 119.4 . . ? C4' C5' C6' 120.7(3) . . ? C4' C5' H5'A 119.7 . . ? C6' C5' H5'A 119.7 . . ? C5' C6' C1' 117.2(2) . . ? C5' C6' C7' 119.8(2) . . ? C1' C6' C7' 122.9(2) . . ? C8' C7' O3' 110.1(2) . . ? C8' C7' C6' 133.4(2) . . ? O3' C7' C6' 116.6(2) . . ? C7' C8' C9' 104.4(2) . . ? C7' C8' H8'A 127.8 . . ? C9' C8' H8'A 127.8 . . ? N2' C9' C8' 111.4(2) . . ? N2' C9' C10' 119.4(2) . . ? C8' C9' C10' 129.2(2) . . ? C15' C10' C11' 120.9(2) . . ? C15' C10' C9' 119.6(2) . . ? C11' C10' C9' 119.6(2) . . ? C12' C11' C10' 118.1(3) . . ? C12' C11' C16' 120.1(3) . . ? C10' C11' C16' 121.7(2) . . ? C13' C12' C11' 122.8(3) . . ? C13' C12' H12A 118.6 . . ? C11' C12' H12A 118.6 . . ? C12' C13' C14' 117.6(3) . . ? C12' C13' C17' 121.7(3) . . ? C14' C13' C17' 120.7(3) . . ? C13' C14' C15' 122.6(3) . . ? C13' C14' H14A 118.7 . . ? C15' C14' H14A 118.7 . . ? C10' C15' C14' 117.9(3) . . ? C10' C15' C18' 122.8(3) . . ? C14' C15' C18' 119.3(3) . . ? C11' C16' H16A 109.5 . . ? C11' C16' H16B 109.5 . . ? H16A C16' H16B 109.5 . . ? C11' C16' H16C 109.5 . . ? H16A C16' H16C 109.5 . . ? H16B C16' H16C 109.5 . . ? C13' C17' H17A 109.5 . . ? C13' C17' H17B 109.5 . . ? H17A C17' H17B 109.5 . . ? C13' C17' H17C 109.5 . . ? H17A C17' H17C 109.5 . . ? H17B C17' H17C 109.5 . . ? C15' C18' H18A 109.5 . . ? C15' C18' H18B 109.5 . . ? H18A C18' H18B 109.5 . . ? C15' C18' H18C 109.5 . . ? H18A C18' H18C 109.5 . . ? H18B C18' H18C 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 O3 N2 C9 -0.2(4) . . . . ? O2 N1 C1 C2 -153.7(3) . . . . ? O1 N1 C1 C2 26.6(4) . . . . ? O2 N1 C1 C6 23.7(4) . . . . ? O1 N1 C1 C6 -156.0(3) . . . . ? C6 C1 C2 C3 1.1(5) . . . . ? N1 C1 C2 C3 178.4(3) . . . . ? C1 C2 C3 C4 -0.7(5) . . . . ? C2 C3 C4 C5 -0.4(5) . . . . ? C3 C4 C5 C6 1.3(5) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? N1 C1 C6 C5 -177.5(2) . . . . ? C2 C1 C6 C7 -177.7(3) . . . . ? N1 C1 C6 C7 5.1(4) . . . . ? C4 C5 C6 C1 -0.9(4) . . . . ? C4 C5 C6 C7 176.7(3) . . . . ? N2 O3 C7 C8 0.8(3) . . . . ? N2 O3 C7 C6 -179.6(2) . . . . ? C1 C6 C7 C8 -119.7(4) . . . . ? C5 C6 C7 C8 63.0(4) . . . . ? C1 C6 C7 O3 60.8(4) . . . . ? C5 C6 C7 O3 -116.6(3) . . . . ? O3 C7 C8 C9 -1.0(3) . . . . ? C6 C7 C8 C9 179.5(3) . . . . ? O3 N2 C9 C8 -0.4(4) . . . . ? O3 N2 C9 C10 177.5(2) . . . . ? C7 C8 C9 N2 0.9(4) . . . . ? C7 C8 C9 C10 -176.8(3) . . . . ? N2 C9 C10 C11 105.0(3) . . . . ? C8 C9 C10 C11 -77.5(4) . . . . ? N2 C9 C10 C15 -76.6(4) . . . . ? C8 C9 C10 C15 100.9(3) . . . . ? C15 C10 C11 C12 0.7(4) . . . . ? C9 C10 C11 C12 179.0(2) . . . . ? C15 C10 C11 C16 179.3(2) . . . . ? C9 C10 C11 C16 -2.4(4) . . . . ? C10 C11 C12 C13 -0.8(4) . . . . ? C16 C11 C12 C13 -179.4(3) . . . . ? C11 C12 C13 C14 1.0(4) . . . . ? C11 C12 C13 C17 -178.8(3) . . . . ? C12 C13 C14 C15 -1.0(4) . . . . ? C17 C13 C14 C15 178.8(3) . . . . ? C13 C14 C15 C10 0.9(4) . . . . ? C13 C14 C15 C18 -176.9(3) . . . . ? C11 C10 C15 C14 -0.7(4) . . . . ? C9 C10 C15 C14 -179.0(2) . . . . ? C11 C10 C15 C18 177.1(3) . . . . ? C9 C10 C15 C18 -1.3(4) . . . . ? C7' O3' N2' C9' 1.0(3) . . . . ? O2' N1' C1' C2' 142.2(3) . . . . ? O1' N1' C1' C2' -36.5(3) . . . . ? O2' N1' C1' C6' -36.4(4) . . . . ? O1' N1' C1' C6' 144.9(3) . . . . ? C6' C1' C2' C3' 1.6(4) . . . . ? N1' C1' C2' C3' -177.0(3) . . . . ? C1' C2' C3' C4' -1.3(4) . . . . ? C2' C3' C4' C5' 0.4(5) . . . . ? C3' C4' C5' C6' 0.3(4) . . . . ? C4' C5' C6' C1' 0.0(4) . . . . ? C4' C5' C6' C7' -175.8(3) . . . . ? C2' C1' C6' C5' -0.9(4) . . . . ? N1' C1' C6' C5' 177.6(2) . . . . ? C2' C1' C6' C7' 174.7(3) . . . . ? N1' C1' C6' C7' -6.8(4) . . . . ? N2' O3' C7' C8' -1.3(3) . . . . ? N2' O3' C7' C6' 178.6(3) . . . . ? C5' C6' C7' C8' -57.1(5) . . . . ? C1' C6' C7' C8' 127.4(3) . . . . ? C5' C6' C7' O3' 123.0(3) . . . . ? C1' C6' C7' O3' -52.5(4) . . . . ? O3' C7' C8' C9' 1.1(3) . . . . ? C6' C7' C8' C9' -178.8(3) . . . . ? O3' N2' C9' C8' -0.3(3) . . . . ? O3' N2' C9' C10' -178.4(3) . . . . ? C7' C8' C9' N2' -0.5(3) . . . . ? C7' C8' C9' C10' 177.4(3) . . . . ? N2' C9' C10' C15' 67.3(4) . . . . ? C8' C9' C10' C15' -110.4(3) . . . . ? N2' C9' C10' C11' -113.5(3) . . . . ? C8' C9' C10' C11' 68.8(4) . . . . ? C15' C10' C11' C12' -1.6(4) . . . . ? C9' C10' C11' C12' 179.2(2) . . . . ? C15' C10' C11' C16' 179.5(3) . . . . ? C9' C10' C11' C16' 0.3(4) . . . . ? C10' C11' C12' C13' 1.1(4) . . . . ? C16' C11' C12' C13' 180.0(3) . . . . ? C11' C12' C13' C14' -0.4(4) . . . . ? C11' C12' C13' C17' 179.0(3) . . . . ? C12' C13' C14' C15' 0.3(5) . . . . ? C17' C13' C14' C15' -179.2(3) . . . . ? C11' C10' C15' C14' 1.5(4) . . . . ? C9' C10' C15' C14' -179.4(2) . . . . ? C11' C10' C15' C18' -177.3(3) . . . . ? C9' C10' C15' C18' 1.9(4) . . . . ? C13' C14' C15' C10' -0.8(4) . . . . ? C13' C14' C15' C18' 178.0(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.349 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.055 # Attachment 'rc47(13g).cif' data_rc47 _database_code_depnum_ccdc_archive 'CCDC 880840' #TrackingRef 'rc47(13g).cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 Cl N2 O3' _chemical_formula_weight 356.80 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.8541(16) _cell_length_b 7.1382(7) _cell_length_c 16.7066(17) _cell_angle_alpha 90.00 _cell_angle_beta 114.406(2) _cell_angle_gamma 90.00 _cell_volume 1721.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5062 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 28.11 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9135 _exptl_absorpt_correction_T_max 0.9577 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector Bruker Apex' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18222 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3747 _reflns_number_gt 3488 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0739P)^2^+0.9255P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3747 _refine_ls_number_parameters 294 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 Cl1 Cl 0.21009(3) 0.54641(5) 0.41446(3) 0.03155(14) Uani 1 1 d . . . O1 O 0.27131(8) 0.01938(16) 0.43774(8) 0.0319(3) Uani 1 1 d . . . O2 O 0.39372(10) 0.2070(3) 0.60491(10) 0.0617(5) Uani 1 1 d . . . O3 O 0.53964(10) 0.1653(3) 0.65916(10) 0.0620(5) Uani 1 1 d . . . N1 N 0.17894(10) 0.0082(2) 0.42930(10) 0.0322(3) Uani 1 1 d . . . N2 N 0.46642(10) 0.1995(2) 0.59780(9) 0.0346(3) Uani 1 1 d . . . C1 C 0.30320(14) 0.2936(4) 0.27042(12) 0.0453(5) Uani 1 1 d . . . C2 C 0.38952(11) 0.2852(2) 0.35516(11) 0.0305(4) Uani 1 1 d . . . C3 C 0.47623(13) 0.3166(3) 0.35457(13) 0.0373(4) Uani 1 1 d . . . C4 C 0.55649(12) 0.3067(3) 0.43053(13) 0.0376(4) Uani 1 1 d . . . C5 C 0.55297(11) 0.2663(2) 0.51015(12) 0.0319(4) Uani 1 1 d . . . C6 C 0.46731(11) 0.2362(2) 0.51122(11) 0.0262(3) Uani 1 1 d . . . C7 C 0.38484(10) 0.2432(2) 0.43531(10) 0.0241(3) Uani 1 1 d . . . C8 C 0.29288(10) 0.2014(2) 0.43392(10) 0.0243(3) Uani 1 1 d . . . C9 C 0.21880(10) 0.3079(2) 0.42277(9) 0.0229(3) Uani 1 1 d . . . C10 C 0.14857(10) 0.1813(2) 0.42021(9) 0.0229(3) Uani 1 1 d . . . C11 C 0.05148(10) 0.2240(2) 0.40600(10) 0.0224(3) Uani 1 1 d . . . C12 C 0.02690(11) 0.2352(2) 0.47741(10) 0.0242(3) Uani 1 1 d . . . C13 C -0.06579(11) 0.2636(2) 0.46021(11) 0.0268(3) Uani 1 1 d . . . C14 C -0.13348(11) 0.2823(2) 0.37516(11) 0.0275(3) Uani 1 1 d . . . C15 C -0.10627(10) 0.2794(2) 0.30541(10) 0.0259(3) Uani 1 1 d . . . C16 C -0.01412(10) 0.2516(2) 0.31962(10) 0.0235(3) Uani 1 1 d . . . C17 C 0.09765(13) 0.2182(3) 0.57070(11) 0.0316(4) Uani 1 1 d . . . C18 C -0.23403(13) 0.3026(3) 0.35831(15) 0.0396(4) Uani 1 1 d . . . C19 C 0.01347(12) 0.2517(3) 0.24346(11) 0.0285(3) Uani 1 1 d . . . H1A H 0.267(2) 0.406(4) 0.270(2) 0.087(10) Uiso 1 1 d . . . H1B H 0.2651(19) 0.188(4) 0.2657(17) 0.061(7) Uiso 1 1 d . . . H1C H 0.3176(18) 0.310(4) 0.2215(18) 0.062(7) Uiso 1 1 d . . . H3 H 0.4776(14) 0.342(3) 0.3028(14) 0.040(5) Uiso 1 1 d . . . H4 H 0.6122(15) 0.333(3) 0.4262(14) 0.041(5) Uiso 1 1 d . . . H5 H 0.6088(15) 0.259(3) 0.5642(15) 0.039(6) Uiso 1 1 d . . . H13 H -0.0840(13) 0.271(3) 0.5093(13) 0.033(5) Uiso 1 1 d . . . H15 H -0.1514(14) 0.297(3) 0.2455(13) 0.034(5) Uiso 1 1 d . . . H17A H 0.099(2) 0.319(5) 0.600(2) 0.078(9) Uiso 1 1 d . . . H17B H 0.088(2) 0.110(4) 0.599(2) 0.081(9) Uiso 1 1 d . . . H17C H 0.157(2) 0.209(4) 0.5752(19) 0.078(9) Uiso 1 1 d . . . H18A H -0.246(2) 0.413(4) 0.3813(18) 0.068(8) Uiso 1 1 d . . . H18B H -0.2716(19) 0.313(4) 0.2987(19) 0.066(8) Uiso 1 1 d . . . H18C H -0.255(2) 0.197(4) 0.3850(19) 0.073(8) Uiso 1 1 d . . . H19A H 0.0406(17) 0.133(4) 0.2393(16) 0.058(7) Uiso 1 1 d . . . H19B H 0.0579(17) 0.351(4) 0.2512(15) 0.054(6) Uiso 1 1 d . . . H19C H -0.0369(15) 0.272(3) 0.1896(15) 0.040(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0259(2) 0.0219(2) 0.0472(3) 0.00084(14) 0.01542(18) -0.00025(13) O1 0.0235(6) 0.0248(6) 0.0496(7) 0.0013(5) 0.0173(5) 0.0026(4) O2 0.0343(8) 0.1186(15) 0.0361(7) 0.0128(8) 0.0182(6) 0.0041(8) O3 0.0387(8) 0.0948(13) 0.0386(8) 0.0195(8) 0.0020(6) 0.0076(8) N1 0.0255(7) 0.0277(7) 0.0462(8) 0.0021(6) 0.0176(6) -0.0027(6) N2 0.0303(7) 0.0385(8) 0.0307(7) 0.0042(6) 0.0082(6) 0.0012(6) C1 0.0353(10) 0.0732(15) 0.0274(9) -0.0027(9) 0.0129(8) -0.0035(10) C2 0.0271(8) 0.0362(9) 0.0309(8) -0.0058(6) 0.0145(7) -0.0018(6) C3 0.0367(9) 0.0457(10) 0.0392(9) -0.0065(8) 0.0254(8) -0.0043(8) C4 0.0254(8) 0.0412(10) 0.0530(11) -0.0098(8) 0.0229(8) -0.0048(7) C5 0.0203(7) 0.0301(8) 0.0427(9) -0.0048(7) 0.0104(7) 0.0012(6) C6 0.0223(7) 0.0234(7) 0.0323(8) -0.0008(6) 0.0107(6) 0.0017(6) C7 0.0191(7) 0.0251(7) 0.0294(7) -0.0026(6) 0.0114(6) 0.0009(5) C8 0.0210(7) 0.0248(7) 0.0271(7) -0.0004(6) 0.0099(6) -0.0009(6) C9 0.0200(7) 0.0237(7) 0.0259(7) -0.0013(5) 0.0104(6) -0.0011(5) C10 0.0213(7) 0.0234(7) 0.0250(7) -0.0001(5) 0.0105(6) -0.0001(5) C11 0.0200(7) 0.0217(7) 0.0271(7) -0.0007(5) 0.0113(6) -0.0024(5) C12 0.0257(7) 0.0218(7) 0.0266(7) -0.0013(5) 0.0124(6) -0.0028(5) C13 0.0280(8) 0.0262(8) 0.0317(8) -0.0018(6) 0.0179(7) -0.0014(6) C14 0.0234(7) 0.0252(7) 0.0368(8) -0.0020(6) 0.0155(7) -0.0008(6) C15 0.0213(7) 0.0280(8) 0.0273(7) 0.0007(6) 0.0090(6) 0.0000(6) C16 0.0239(7) 0.0230(7) 0.0259(7) -0.0009(5) 0.0127(6) -0.0019(5) C17 0.0327(9) 0.0363(9) 0.0245(8) -0.0016(7) 0.0106(7) -0.0008(7) C18 0.0253(9) 0.0480(11) 0.0495(11) 0.0000(9) 0.0194(8) 0.0028(8) C19 0.0268(8) 0.0356(9) 0.0258(8) 0.0005(6) 0.0136(7) 0.0000(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 Cl1 C9 1.7088(16) . ? O1 C8 1.3517(19) . ? O1 N1 1.4143(18) . ? O2 N2 1.208(2) . ? O3 N2 1.2144(19) . ? N1 C10 1.312(2) . ? N2 C6 1.476(2) . ? C1 C2 1.510(2) . ? C1 H1A 0.98(3) . ? C1 H1B 0.95(3) . ? C1 H1C 0.94(3) . ? C2 C3 1.397(2) . ? C2 C7 1.404(2) . ? C3 C4 1.378(3) . ? C3 H3 0.89(2) . ? C4 C5 1.385(3) . ? C4 H4 0.93(2) . ? C5 C6 1.382(2) . ? C5 H5 0.97(2) . ? C6 C7 1.396(2) . ? C7 C8 1.479(2) . ? C8 C9 1.346(2) . ? C9 C10 1.421(2) . ? C10 C11 1.489(2) . ? C11 C16 1.401(2) . ? C11 C12 1.402(2) . ? C12 C13 1.391(2) . ? C12 C17 1.502(2) . ? C13 C14 1.389(2) . ? C13 H13 0.98(2) . ? C14 C15 1.400(2) . ? C14 C18 1.507(2) . ? C15 C16 1.394(2) . ? C15 H15 0.97(2) . ? C16 C19 1.507(2) . ? C17 H17A 0.86(3) . ? C17 H17B 0.95(3) . ? C17 H17C 0.92(3) . ? C18 H18A 0.93(3) . ? C18 H18B 0.93(3) . ? C18 H18C 1.00(3) . ? C19 H19A 0.97(3) . ? C19 H19B 0.97(3) . ? C19 H19C 0.94(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O1 N1 108.73(11) . . ? C10 N1 O1 105.91(12) . . ? O2 N2 O3 122.98(16) . . ? O2 N2 C6 118.97(14) . . ? O3 N2 C6 118.04(15) . . ? C2 C1 H1A 109.6(19) . . ? C2 C1 H1B 110.3(16) . . ? H1A C1 H1B 108(2) . . ? C2 C1 H1C 111.6(16) . . ? H1A C1 H1C 104(2) . . ? H1B C1 H1C 114(2) . . ? C3 C2 C7 118.75(15) . . ? C3 C2 C1 120.03(16) . . ? C7 C2 C1 121.21(15) . . ? C4 C3 C2 121.47(17) . . ? C4 C3 H3 121.3(13) . . ? C2 C3 H3 117.3(14) . . ? C3 C4 C5 120.46(16) . . ? C3 C4 H4 117.4(13) . . ? C5 C4 H4 122.1(13) . . ? C6 C5 C4 118.33(16) . . ? C6 C5 H5 120.2(13) . . ? C4 C5 H5 121.5(13) . . ? C5 C6 C7 122.61(15) . . ? C5 C6 N2 116.59(14) . . ? C7 C6 N2 120.79(14) . . ? C6 C7 C2 118.38(14) . . ? C6 C7 C8 123.65(14) . . ? C2 C7 C8 117.93(13) . . ? C9 C8 O1 109.05(13) . . ? C9 C8 C7 133.35(14) . . ? O1 C8 C7 117.39(13) . . ? C8 C9 C10 105.82(14) . . ? C8 C9 Cl1 127.65(12) . . ? C10 C9 Cl1 126.53(11) . . ? N1 C10 C9 110.49(13) . . ? N1 C10 C11 121.15(13) . . ? C9 C10 C11 128.32(13) . . ? C16 C11 C12 121.29(13) . . ? C16 C11 C10 118.16(13) . . ? C12 C11 C10 120.56(13) . . ? C13 C12 C11 118.29(14) . . ? C13 C12 C17 119.89(14) . . ? C11 C12 C17 121.82(14) . . ? C14 C13 C12 121.96(14) . . ? C14 C13 H13 118.8(12) . . ? C12 C13 H13 119.2(12) . . ? C13 C14 C15 118.46(14) . . ? C13 C14 C18 120.74(15) . . ? C15 C14 C18 120.79(16) . . ? C16 C15 C14 121.47(14) . . ? C16 C15 H15 118.0(11) . . ? C14 C15 H15 120.5(11) . . ? C15 C16 C11 118.38(13) . . ? C15 C16 C19 120.38(14) . . ? C11 C16 C19 121.25(13) . . ? C12 C17 H17A 111(2) . . ? C12 C17 H17B 112.6(18) . . ? H17A C17 H17B 111(3) . . ? C12 C17 H17C 113.1(19) . . ? H17A C17 H17C 103(3) . . ? H17B C17 H17C 106(2) . . ? C14 C18 H18A 112.8(18) . . ? C14 C18 H18B 111.6(16) . . ? H18A C18 H18B 103(2) . . ? C14 C18 H18C 111.1(16) . . ? H18A C18 H18C 107(2) . . ? H18B C18 H18C 111(2) . . ? C16 C19 H19A 110.7(15) . . ? C16 C19 H19B 109.7(14) . . ? H19A C19 H19B 109(2) . . ? C16 C19 H19C 112.4(13) . . ? H19A C19 H19C 107.3(19) . . ? H19B C19 H19C 107.4(19) . . ? 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 C8 O1 N1 C10 0.43(17) . . . . ? C7 C2 C3 C4 0.1(3) . . . . ? C1 C2 C3 C4 -178.83(19) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C4 C5 C6 C7 0.6(2) . . . . ? C4 C5 C6 N2 -178.13(15) . . . . ? O2 N2 C6 C5 166.30(18) . . . . ? O3 N2 C6 C5 -12.7(2) . . . . ? O2 N2 C6 C7 -12.5(2) . . . . ? O3 N2 C6 C7 168.47(17) . . . . ? C5 C6 C7 C2 -1.0(2) . . . . ? N2 C6 C7 C2 177.76(14) . . . . ? C5 C6 C7 C8 176.56(15) . . . . ? N2 C6 C7 C8 -4.7(2) . . . . ? C3 C2 C7 C6 0.6(2) . . . . ? C1 C2 C7 C6 179.50(17) . . . . ? C3 C2 C7 C8 -177.10(15) . . . . ? C1 C2 C7 C8 1.8(2) . . . . ? N1 O1 C8 C9 -0.46(17) . . . . ? N1 O1 C8 C7 -175.85(13) . . . . ? C6 C7 C8 C9 109.4(2) . . . . ? C2 C7 C8 C9 -73.0(2) . . . . ? C6 C7 C8 O1 -76.56(19) . . . . ? C2 C7 C8 O1 100.96(17) . . . . ? O1 C8 C9 C10 0.31(17) . . . . ? C7 C8 C9 C10 174.67(16) . . . . ? O1 C8 C9 Cl1 179.66(11) . . . . ? C7 C8 C9 Cl1 -6.0(3) . . . . ? O1 N1 C10 C9 -0.24(17) . . . . ? O1 N1 C10 C11 177.59(13) . . . . ? C8 C9 C10 N1 -0.03(17) . . . . ? Cl1 C9 C10 N1 -179.40(12) . . . . ? C8 C9 C10 C11 -177.66(14) . . . . ? Cl1 C9 C10 C11 3.0(2) . . . . ? N1 C10 C11 C16 -96.74(18) . . . . ? C9 C10 C11 C16 80.66(19) . . . . ? N1 C10 C11 C12 82.99(19) . . . . ? C9 C10 C11 C12 -99.61(18) . . . . ? C16 C11 C12 C13 3.7(2) . . . . ? C10 C11 C12 C13 -175.98(13) . . . . ? C16 C11 C12 C17 -175.99(14) . . . . ? C10 C11 C12 C17 4.3(2) . . . . ? C11 C12 C13 C14 -0.5(2) . . . . ? C17 C12 C13 C14 179.26(15) . . . . ? C12 C13 C14 C15 -2.5(2) . . . . ? C12 C13 C14 C18 176.68(16) . . . . ? C13 C14 C15 C16 2.3(2) . . . . ? C18 C14 C15 C16 -176.86(16) . . . . ? C14 C15 C16 C11 0.8(2) . . . . ? C14 C15 C16 C19 -179.19(15) . . . . ? C12 C11 C16 C15 -3.9(2) . . . . ? C10 C11 C16 C15 175.82(13) . . . . ? C12 C11 C16 C19 176.10(14) . . . . ? C10 C11 C16 C19 -4.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.783 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.061 # Attachment 'rc71a(11).cif' data_rc71a _database_code_depnum_ccdc_archive 'CCDC 904545' #TrackingRef 'rc71a(11).cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N2 O4' _chemical_formula_weight 298.29 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.238(4) _cell_length_b 8.006(3) _cell_length_c 28.867(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2828.3(17) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 1249 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 19.34 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9650 _exptl_absorpt_correction_T_max 0.9980 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Bruker Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18841 _diffrn_reflns_av_R_equivalents 0.0889 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2501 _reflns_number_gt 1531 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0944P)^2^+1.3864P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2501 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1151 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1919 _refine_ls_wR_factor_gt 0.1590 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0182(2) 1.0694(4) 0.44778(10) 0.0542(8) Uani 1 1 d . . . O2 O -0.0889(2) 0.9936(4) 0.38830(10) 0.0575(9) Uani 1 1 d . . . O3 O 0.1454(2) 0.7649(3) 0.19905(8) 0.0427(7) Uani 1 1 d . . . O4 O 0.6365(2) 1.0302(3) 0.42133(9) 0.0477(8) Uani 1 1 d . . . N1 N 0.1272(3) 1.0850(4) 0.45696(13) 0.0497(10) Uani 1 1 d . . . N2 N 0.0043(3) 1.0152(4) 0.40137(12) 0.0452(9) Uani 1 1 d . . . C1 C 0.1779(3) 1.0420(4) 0.41696(13) 0.0352(9) Uani 1 1 d . . . C2 C 0.1024(3) 0.9984(4) 0.38171(13) 0.0352(9) Uani 1 1 d . . . C3 C 0.1139(3) 0.9432(4) 0.33317(13) 0.0351(9) Uani 1 1 d . . . C4 C 0.1899(3) 1.0164(5) 0.30376(13) 0.0361(9) Uani 1 1 d . . . C5 C 0.2026(3) 0.9610(5) 0.25864(14) 0.0370(9) Uani 1 1 d . . . C6 C 0.1384(3) 0.8320(5) 0.24234(12) 0.0319(8) Uani 1 1 d . . . C7 C 0.0595(3) 0.7601(5) 0.27143(14) 0.0391(10) Uani 1 1 d . . . C8 C 0.0480(3) 0.8143(5) 0.31590(14) 0.0375(9) Uani 1 1 d . . . C9 C 0.2333(4) 0.8226(7) 0.17019(16) 0.0470(11) Uani 1 1 d . . . C10 C 0.2977(3) 1.0437(4) 0.41693(12) 0.0334(9) Uani 1 1 d . . . C11 C 0.3586(3) 0.9407(5) 0.38770(14) 0.0349(9) Uani 1 1 d . . . C12 C 0.4715(3) 0.9376(5) 0.39032(13) 0.0372(9) Uani 1 1 d . . . C13 C 0.5260(3) 1.0402(4) 0.42178(12) 0.0354(9) Uani 1 1 d . . . C14 C 0.4668(3) 1.1441(5) 0.45107(14) 0.0383(9) Uani 1 1 d . . . C15 C 0.3538(3) 1.1448(5) 0.44824(13) 0.0367(9) Uani 1 1 d . . . C16 C 0.6956(4) 1.1370(6) 0.45220(16) 0.0467(11) Uani 1 1 d . . . H4 H 0.232(3) 1.108(5) 0.3161(12) 0.038(10) Uiso 1 1 d . . . H5 H 0.253(3) 1.012(4) 0.2388(12) 0.041(10) Uiso 1 1 d . . . H7 H 0.020(3) 0.673(4) 0.2601(10) 0.023(9) Uiso 1 1 d . . . H8 H -0.001(3) 0.758(5) 0.3364(13) 0.049(11) Uiso 1 1 d . . . H9A H 0.314(4) 0.809(6) 0.1864(15) 0.082(15) Uiso 1 1 d . . . H9B H 0.222(3) 0.940(6) 0.1633(13) 0.055(12) Uiso 1 1 d . . . H9C H 0.227(3) 0.758(5) 0.1443(14) 0.048(12) Uiso 1 1 d . . . H11 H 0.328(3) 0.873(5) 0.3663(12) 0.039(11) Uiso 1 1 d . . . H12 H 0.516(3) 0.866(5) 0.3694(14) 0.057(12) Uiso 1 1 d . . . H14 H 0.500(3) 1.217(5) 0.4741(13) 0.046(11) Uiso 1 1 d . . . H15 H 0.315(3) 1.216(5) 0.4701(12) 0.044(11) Uiso 1 1 d . . . H16A H 0.767(5) 1.100(6) 0.4463(17) 0.086(17) Uiso 1 1 d . . . H16B H 0.687(3) 1.254(5) 0.4447(12) 0.039(10) Uiso 1 1 d . . . H16C H 0.678(3) 1.112(4) 0.4849(13) 0.036(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.063(2) 0.0542(18) 0.0457(17) -0.0031(14) 0.0165(14) 0.0040(15) O2 0.0456(19) 0.066(2) 0.061(2) -0.0044(16) 0.0007(15) -0.0009(15) O3 0.0363(16) 0.0486(16) 0.0433(16) 0.0028(13) -0.0009(12) -0.0047(13) O4 0.0373(17) 0.0523(18) 0.0534(17) -0.0135(14) -0.0011(13) 0.0039(13) N1 0.0286(19) 0.0384(19) 0.082(3) 0.0125(18) 0.0051(18) -0.0008(15) N2 0.033(2) 0.0361(19) 0.066(2) 0.0092(17) -0.0018(17) 0.0012(15) C1 0.036(2) 0.028(2) 0.041(2) 0.0045(17) 0.0155(18) 0.0044(16) C2 0.028(2) 0.031(2) 0.046(2) 0.0077(17) 0.0131(17) 0.0047(16) C3 0.032(2) 0.029(2) 0.045(2) 0.0075(17) 0.0044(17) 0.0028(16) C4 0.031(2) 0.033(2) 0.044(2) 0.0007(18) 0.0017(17) -0.0021(17) C5 0.031(2) 0.033(2) 0.047(2) 0.0114(19) 0.0044(18) 0.0001(17) C6 0.0298(19) 0.034(2) 0.032(2) 0.0038(16) -0.0038(15) 0.0051(16) C7 0.026(2) 0.036(2) 0.055(3) 0.003(2) -0.0007(18) -0.0068(17) C8 0.027(2) 0.036(2) 0.050(3) 0.006(2) 0.0067(18) 0.0001(16) C9 0.044(3) 0.052(3) 0.045(3) 0.003(2) 0.006(2) 0.000(2) C10 0.038(2) 0.0273(19) 0.035(2) 0.0053(17) 0.0068(16) 0.0027(16) C11 0.040(2) 0.027(2) 0.038(2) -0.0009(18) 0.0026(18) 0.0014(17) C12 0.041(2) 0.032(2) 0.039(2) -0.0015(18) 0.0042(18) 0.0029(18) C13 0.037(2) 0.032(2) 0.038(2) 0.0020(17) 0.0030(17) 0.0026(17) C14 0.043(2) 0.033(2) 0.039(2) -0.0009(19) 0.0031(18) -0.0005(18) C15 0.042(2) 0.030(2) 0.038(2) 0.0017(18) 0.0076(18) 0.0052(18) C16 0.051(3) 0.046(3) 0.043(3) -0.004(2) 0.000(2) -0.003(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 N1 1.366(4) . ? O1 N2 1.418(4) . ? O2 N2 1.214(4) . ? O3 C6 1.363(4) . ? O3 C9 1.437(5) . ? O4 C13 1.355(4) . ? O4 C16 1.431(5) . ? N1 C1 1.355(5) . ? N2 C2 1.334(5) . ? C1 C2 1.418(5) . ? C1 C10 1.467(5) . ? C2 C3 1.476(5) . ? C3 C4 1.389(5) . ? C3 C8 1.401(5) . ? C4 C5 1.385(5) . ? C4 H4 0.97(4) . ? C5 C6 1.380(5) . ? C5 H5 0.93(4) . ? C6 C7 1.403(5) . ? C7 C8 1.362(5) . ? C7 H7 0.91(3) . ? C8 H8 0.96(4) . ? C9 H9A 1.10(5) . ? C9 H9B 0.98(4) . ? C9 H9C 0.92(4) . ? C10 C15 1.394(5) . ? C10 C11 1.395(5) . ? C11 C12 1.384(5) . ? C11 H11 0.91(4) . ? C12 C13 1.394(5) . ? C12 H12 1.00(4) . ? C13 C14 1.390(5) . ? C14 C15 1.385(5) . ? C14 H14 0.97(4) . ? C15 H15 0.97(4) . ? C16 H16A 0.94(6) . ? C16 H16B 0.97(4) . ? C16 H16C 0.99(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 N1 O1 N2 109.1(3) . . ? C6 O3 C9 116.9(3) . . ? C13 O4 C16 117.6(3) . . ? C1 N1 O1 105.0(3) . . ? O2 N2 C2 134.3(4) . . ? O2 N2 O1 116.7(3) . . ? C2 N2 O1 109.0(3) . . ? N1 C1 C2 112.1(3) . . ? N1 C1 C10 117.1(3) . . ? C2 C1 C10 130.8(3) . . ? N2 C2 C1 104.8(3) . . ? N2 C2 C3 121.3(4) . . ? C1 C2 C3 133.8(3) . . ? C4 C3 C8 118.6(4) . . ? C4 C3 C2 121.2(3) . . ? C8 C3 C2 120.2(3) . . ? C5 C4 C3 121.0(4) . . ? C5 C4 H4 122(2) . . ? C3 C4 H4 117(2) . . ? C6 C5 C4 119.8(4) . . ? C6 C5 H5 120(2) . . ? C4 C5 H5 121(2) . . ? O3 C6 C5 124.9(3) . . ? O3 C6 C7 115.5(3) . . ? C5 C6 C7 119.7(4) . . ? C8 C7 C6 120.3(4) . . ? C8 C7 H7 122(2) . . ? C6 C7 H7 118(2) . . ? C7 C8 C3 120.7(4) . . ? C7 C8 H8 120(2) . . ? C3 C8 H8 119(2) . . ? O3 C9 H9A 113(2) . . ? O3 C9 H9B 109(2) . . ? H9A C9 H9B 108(4) . . ? O3 C9 H9C 103(3) . . ? H9A C9 H9C 112(3) . . ? H9B C9 H9C 112(3) . . ? C15 C10 C11 118.1(3) . . ? C15 C10 C1 119.8(3) . . ? C11 C10 C1 122.0(3) . . ? C12 C11 C10 120.7(4) . . ? C12 C11 H11 116(2) . . ? C10 C11 H11 123(2) . . ? C11 C12 C13 120.2(4) . . ? C11 C12 H12 122(2) . . ? C13 C12 H12 118(2) . . ? O4 C13 C14 124.2(3) . . ? O4 C13 C12 115.9(3) . . ? C14 C13 C12 119.9(4) . . ? C15 C14 C13 119.2(4) . . ? C15 C14 H14 117(2) . . ? C13 C14 H14 124(2) . . ? C14 C15 C10 121.8(4) . . ? C14 C15 H15 117(2) . . ? C10 C15 H15 121(2) . . ? O4 C16 H16A 100(3) . . ? O4 C16 H16B 112(2) . . ? H16A C16 H16B 112(4) . . ? O4 C16 H16C 111(2) . . ? H16A C16 H16C 108(4) . . ? H16B C16 H16C 113(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 N2 O1 N1 C1 0.3(4) . . . . ? N1 O1 N2 O2 179.1(3) . . . . ? N1 O1 N2 C2 -0.5(4) . . . . ? O1 N1 C1 C2 0.0(4) . . . . ? O1 N1 C1 C10 -178.7(3) . . . . ? O2 N2 C2 C1 -179.0(4) . . . . ? O1 N2 C2 C1 0.5(4) . . . . ? O2 N2 C2 C3 0.5(6) . . . . ? O1 N2 C2 C3 179.9(3) . . . . ? N1 C1 C2 N2 -0.3(4) . . . . ? C10 C1 C2 N2 178.1(4) . . . . ? N1 C1 C2 C3 -179.7(4) . . . . ? C10 C1 C2 C3 -1.2(7) . . . . ? N2 C2 C3 C4 138.9(4) . . . . ? C1 C2 C3 C4 -41.8(6) . . . . ? N2 C2 C3 C8 -41.4(5) . . . . ? C1 C2 C3 C8 137.9(4) . . . . ? C8 C3 C4 C5 -1.6(5) . . . . ? C2 C3 C4 C5 178.2(3) . . . . ? C3 C4 C5 C6 0.6(5) . . . . ? C9 O3 C6 C5 6.3(5) . . . . ? C9 O3 C6 C7 -173.1(3) . . . . ? C4 C5 C6 O3 -178.4(3) . . . . ? C4 C5 C6 C7 1.0(5) . . . . ? O3 C6 C7 C8 178.0(3) . . . . ? C5 C6 C7 C8 -1.5(5) . . . . ? C6 C7 C8 C3 0.4(6) . . . . ? C4 C3 C8 C7 1.1(6) . . . . ? C2 C3 C8 C7 -178.7(3) . . . . ? N1 C1 C10 C15 -24.7(5) . . . . ? C2 C1 C10 C15 156.9(4) . . . . ? N1 C1 C10 C11 152.3(3) . . . . ? C2 C1 C10 C11 -26.1(6) . . . . ? C15 C10 C11 C12 1.0(5) . . . . ? C1 C10 C11 C12 -176.1(3) . . . . ? C10 C11 C12 C13 -1.3(5) . . . . ? C16 O4 C13 C14 -1.7(5) . . . . ? C16 O4 C13 C12 178.3(3) . . . . ? C11 C12 C13 O4 -179.0(3) . . . . ? C11 C12 C13 C14 1.0(5) . . . . ? O4 C13 C14 C15 179.6(3) . . . . ? C12 C13 C14 C15 -0.5(5) . . . . ? C13 C14 C15 C10 0.2(5) . . . . ? C11 C10 C15 C14 -0.5(5) . . . . ? C1 C10 C15 C14 176.7(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.611 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.054