# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1093 _database_code_depnum_ccdc_archive 'CCDC 799949' #TrackingRef '- 799949.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 N O2' _chemical_formula_sum 'C13 H15 N O2' _chemical_formula_weight 217.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 16.8344(14) _cell_length_b 12.0895(7) _cell_length_c 19.8772(13) _cell_angle_alpha 90.00 _cell_angle_beta 117.868(5) _cell_angle_gamma 90.00 _cell_volume 3576.2(5) _cell_formula_units_Z 12 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16274 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22887 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 25.03 _reflns_number_total 6320 _reflns_number_gt 4653 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0738P)^2^+2.0090P] 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 6320 _refine_ls_number_parameters 439 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1605 _refine_ls_wR_factor_gt 0.1459 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.079 _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 0.21620(11) 0.71888(13) 0.57101(10) 0.0422(4) Uani 1 1 d . . . O2 O 0.03743(14) 0.59863(15) 0.35600(11) 0.0590(5) Uani 1 1 d . . . N1 N 0.10872(14) 0.74801(17) 0.41609(11) 0.0433(5) Uani 1 1 d . . . H1 H 0.1485 0.7885 0.4535 0.052 Uiso 1 1 d R . . C1 C 0.21037(16) 0.55193(19) 0.63102(14) 0.0386(6) Uani 1 1 d . . . C2 C 0.26486(18) 0.5968(2) 0.70185(15) 0.0479(6) Uani 1 1 d . . . H2 H 0.2855 0.6708 0.7056 0.057 Uiso 1 1 calc R . . C3 C 0.2899(2) 0.5351(3) 0.76774(18) 0.0608(8) Uani 1 1 d . . . H3 H 0.3273 0.5672 0.8160 0.073 Uiso 1 1 calc R . . C4 C 0.2609(2) 0.4283(3) 0.76339(19) 0.0634(8) Uani 1 1 d . . . H4 H 0.2787 0.3860 0.8084 0.076 Uiso 1 1 calc R . . C5 C 0.2062(2) 0.3831(3) 0.6941(2) 0.0654(9) Uani 1 1 d . . . H5 H 0.1857 0.3092 0.6911 0.078 Uiso 1 1 calc R . . C6 C 0.18029(19) 0.4439(2) 0.62758(18) 0.0545(7) Uani 1 1 d . . . H6 H 0.1419 0.4114 0.5797 0.065 Uiso 1 1 calc R . . C7 C 0.18516(15) 0.62294(19) 0.56137(14) 0.0356(5) Uani 1 1 d . . . C8 C 0.12572(18) 0.5800(2) 0.48888(15) 0.0449(6) Uani 1 1 d . . . H8 H 0.1073 0.5050 0.4849 0.054 Uiso 1 1 calc R . . C9 C 0.09367(16) 0.6433(2) 0.42401(14) 0.0400(6) Uani 1 1 d . . . C10 C 0.05299(17) 0.7912(2) 0.33922(14) 0.0416(6) Uani 1 1 d . . . C11 C 0.01537(18) 0.6809(2) 0.29746(15) 0.0473(6) Uani 1 1 d . . . H11A H -0.0505 0.6858 0.2653 0.057 Uiso 1 1 calc R . . H11B H 0.0432 0.6622 0.2647 0.057 Uiso 1 1 calc R . . C12 C 0.1104(2) 0.8519(3) 0.31154(16) 0.0643(9) Uani 1 1 d . . . H12A H 0.1373 0.9170 0.3436 0.096 Uiso 1 1 calc R . . H12B H 0.0731 0.8755 0.2588 0.096 Uiso 1 1 calc R . . H12C H 0.1581 0.8028 0.3142 0.096 Uiso 1 1 calc R . . C13 C -0.0210(2) 0.8638(3) 0.33924(19) 0.0707(10) Uani 1 1 d . . . H13A H -0.0570 0.8205 0.3568 0.106 Uiso 1 1 calc R . . H13B H -0.0597 0.8907 0.2875 0.106 Uiso 1 1 calc R . . H13C H 0.0060 0.9269 0.3734 0.106 Uiso 1 1 calc R . . O1A O 0.36999(14) 0.30668(17) 0.40150(11) 0.0633(6) Uani 1 1 d . . . O2A O 0.34368(18) 0.4346(2) 0.58165(12) 0.0836(8) Uani 1 1 d . . . N1A N 0.41015(15) 0.30809(19) 0.54714(12) 0.0481(6) Uani 1 1 d . . . H1A H 0.4189 0.2628 0.5166 0.058 Uiso 1 1 d R . . C1A C 0.27954(15) 0.44544(19) 0.31595(13) 0.0359(5) Uani 1 1 d . . . C2A C 0.29143(18) 0.3997(2) 0.25732(14) 0.0471(6) Uani 1 1 d . . . H2A H 0.3244 0.3329 0.2659 0.057 Uiso 1 1 calc R . . C3A C 0.2561(2) 0.4497(3) 0.18658(16) 0.0558(7) Uani 1 1 d . . . H3A H 0.2645 0.4163 0.1471 0.067 Uiso 1 1 calc R . . C4A C 0.20889(19) 0.5474(2) 0.17289(16) 0.0503(7) Uani 1 1 d . . . H4A H 0.1854 0.5823 0.1245 0.060 Uiso 1 1 calc R . . C5A C 0.19627(19) 0.5937(2) 0.23055(16) 0.0514(7) Uani 1 1 d . . . H5A H 0.1636 0.6608 0.2217 0.062 Uiso 1 1 calc R . . C6A C 0.23058(17) 0.5435(2) 0.30093(15) 0.0446(6) Uani 1 1 d . . . H6A H 0.2207 0.5763 0.3398 0.054 Uiso 1 1 calc R . . C7A C 0.32212(15) 0.3906(2) 0.39223(14) 0.0381(5) Uani 1 1 d . . . C8A C 0.30711(18) 0.4328(2) 0.45094(14) 0.0448(6) Uani 1 1 d . . . H8A H 0.2651 0.4910 0.4405 0.054 Uiso 1 1 calc R . . C9A C 0.35244(18) 0.3910(2) 0.52321(15) 0.0462(6) Uani 1 1 d . . . C10A C 0.45808(17) 0.3000(2) 0.63046(14) 0.0458(6) Uani 1 1 d . . . C11A C 0.3934(3) 0.3644(4) 0.64806(19) 0.0904(13) Uani 1 1 d . . . H11C H 0.3522 0.3139 0.6559 0.109 Uiso 1 1 calc R . . H11D H 0.4262 0.4098 0.6944 0.109 Uiso 1 1 calc R . . C12A C 0.5489(3) 0.3528(4) 0.6604(2) 0.1035(15) Uani 1 1 d U . . H12D H 0.5831 0.3160 0.6383 0.155 Uiso 1 1 calc R . . H12E H 0.5811 0.3456 0.7159 0.155 Uiso 1 1 calc R . . H12F H 0.5418 0.4313 0.6466 0.155 Uiso 1 1 calc R . . C13A C 0.4672(3) 0.1803(3) 0.65630(18) 0.0783(10) Uani 1 1 d U . . H13D H 0.4073 0.1473 0.6371 0.117 Uiso 1 1 calc R . . H13E H 0.4983 0.1773 0.7120 0.117 Uiso 1 1 calc R . . H13F H 0.5018 0.1390 0.6364 0.117 Uiso 1 1 calc R . . O1B O 0.16889(11) 0.54651(12) -0.00064(9) 0.0372(4) Uani 1 1 d . . . O2B O 0.42188(12) 0.52481(15) 0.01326(12) 0.0525(5) Uani 1 1 d . . . N1B N 0.33599(14) 0.62979(17) 0.04251(14) 0.0505(6) Uani 1 1 d . . . H1B H 0.2904 0.6484 0.0503 0.061 Uiso 1 1 d R . . C1B C 0.13093(14) 0.36391(18) -0.04712(12) 0.0324(5) Uani 1 1 d . . . C2B C 0.05814(16) 0.3640(2) -0.03179(14) 0.0410(6) Uani 1 1 d . . . H2B H 0.0499 0.4245 -0.0052 0.049 Uiso 1 1 calc R . . C3B C -0.00229(17) 0.2767(2) -0.05491(16) 0.0478(6) Uani 1 1 d . . . H3B H -0.0515 0.2776 -0.0440 0.057 Uiso 1 1 calc R . . C4B C 0.00899(17) 0.1884(2) -0.09385(15) 0.0451(6) Uani 1 1 d . . . H4B H -0.0326 0.1287 -0.1101 0.054 Uiso 1 1 calc R . . C5B C 0.08105(17) 0.1876(2) -0.10897(15) 0.0439(6) Uani 1 1 d . . . H5B H 0.0891 0.1269 -0.1355 0.053 Uiso 1 1 calc R . . C6B C 0.14172(16) 0.27440(19) -0.08596(13) 0.0372(5) Uani 1 1 d . . . H6B H 0.1910 0.2728 -0.0968 0.045 Uiso 1 1 calc R . . C7B C 0.19410(15) 0.46018(18) -0.02034(12) 0.0314(5) Uani 1 1 d . . . C8B C 0.27939(16) 0.45095(19) -0.01740(15) 0.0399(6) Uani 1 1 d . . . H8B H 0.2941 0.3859 -0.0360 0.048 Uiso 1 1 calc R . . C9B C 0.34124(16) 0.5348(2) 0.01197(15) 0.0404(6) Uani 1 1 d . . . C10B C 0.41390(16) 0.7003(2) 0.06203(14) 0.0398(6) Uani 1 1 d . . . C11B C 0.4749(2) 0.6211(3) 0.0505(2) 0.0753(10) Uani 1 1 d U . . H11E H 0.4990 0.6553 0.0186 0.090 Uiso 1 1 calc R . . H11F H 0.5259 0.6004 0.1001 0.090 Uiso 1 1 calc R . . C12B C 0.4504(3) 0.7446(5) 0.1404(2) 0.1106(17) Uani 1 1 d U . . H12G H 0.4702 0.6831 0.1768 0.166 Uiso 1 1 calc R . . H12H H 0.4035 0.7867 0.1452 0.166 Uiso 1 1 calc R . . H12I H 0.5015 0.7931 0.1510 0.166 Uiso 1 1 calc R . . C13B C 0.3859(3) 0.7929(4) 0.0055(3) 0.1057(16) Uani 1 1 d U . . H13G H 0.3324 0.8292 0.0028 0.159 Uiso 1 1 calc R . . H13H H 0.3720 0.7634 -0.0447 0.159 Uiso 1 1 calc R . . H13I H 0.4348 0.8468 0.0213 0.159 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 0.0446(10) 0.0350(9) 0.0453(10) 0.0017(7) 0.0196(8) -0.0046(8) O2 0.0730(13) 0.0382(10) 0.0453(11) -0.0075(8) 0.0105(9) -0.0041(9) N1 0.0464(12) 0.0380(12) 0.0362(11) -0.0030(9) 0.0116(9) -0.0041(10) C1 0.0330(12) 0.0351(13) 0.0513(15) 0.0064(11) 0.0228(11) 0.0072(10) C2 0.0543(16) 0.0436(15) 0.0494(16) 0.0051(12) 0.0274(13) 0.0025(13) C3 0.0655(19) 0.066(2) 0.0514(17) 0.0114(15) 0.0278(15) 0.0046(16) C4 0.0580(18) 0.069(2) 0.069(2) 0.0288(17) 0.0348(16) 0.0095(16) C5 0.0556(17) 0.0519(18) 0.086(2) 0.0258(17) 0.0308(17) -0.0033(15) C6 0.0468(15) 0.0427(15) 0.0665(18) 0.0121(13) 0.0202(14) -0.0019(12) C7 0.0331(11) 0.0315(12) 0.0463(14) 0.0026(10) 0.0219(10) 0.0067(10) C8 0.0506(15) 0.0288(12) 0.0501(15) -0.0007(11) 0.0191(12) 0.0021(11) C9 0.0381(13) 0.0347(13) 0.0434(14) -0.0081(11) 0.0160(11) 0.0022(11) C10 0.0416(13) 0.0388(14) 0.0372(14) -0.0028(10) 0.0123(11) 0.0026(11) C11 0.0483(15) 0.0458(15) 0.0406(14) -0.0058(11) 0.0146(12) -0.0006(12) C12 0.080(2) 0.069(2) 0.0435(16) -0.0081(14) 0.0292(15) -0.0253(17) C13 0.0502(17) 0.063(2) 0.073(2) -0.0208(16) 0.0073(15) 0.0160(15) O1A 0.0742(14) 0.0685(13) 0.0419(11) 0.0016(9) 0.0228(10) 0.0369(11) O2A 0.117(2) 0.0938(17) 0.0571(13) 0.0169(12) 0.0545(14) 0.0567(15) N1A 0.0489(13) 0.0565(14) 0.0380(12) -0.0025(10) 0.0196(10) 0.0147(11) C1A 0.0298(11) 0.0362(13) 0.0397(13) -0.0046(10) 0.0146(10) -0.0037(10) C2A 0.0460(14) 0.0482(15) 0.0445(15) -0.0047(12) 0.0189(12) 0.0094(12) C3A 0.0594(17) 0.0671(19) 0.0454(16) 0.0002(14) 0.0281(13) 0.0143(15) C4A 0.0524(16) 0.0543(17) 0.0466(15) 0.0069(13) 0.0251(13) 0.0066(13) C5A 0.0578(16) 0.0463(15) 0.0525(16) 0.0071(13) 0.0278(13) 0.0113(13) C6A 0.0475(14) 0.0435(14) 0.0464(15) -0.0019(12) 0.0248(12) 0.0054(12) C7A 0.0318(12) 0.0355(13) 0.0435(14) -0.0054(10) 0.0147(10) -0.0006(10) C8A 0.0489(15) 0.0422(14) 0.0476(15) 0.0036(11) 0.0260(12) 0.0104(12) C9A 0.0538(15) 0.0470(15) 0.0487(15) -0.0020(12) 0.0331(13) 0.0070(13) C10A 0.0458(14) 0.0569(16) 0.0349(14) -0.0031(12) 0.0190(11) 0.0012(12) C11A 0.110(3) 0.118(3) 0.056(2) 0.027(2) 0.050(2) 0.061(3) C12A 0.077(2) 0.162(4) 0.064(2) -0.020(2) 0.0275(19) -0.051(3) C13A 0.098(3) 0.072(2) 0.0476(18) 0.0009(16) 0.0191(17) 0.005(2) O1B 0.0403(9) 0.0300(8) 0.0459(10) -0.0023(7) 0.0240(8) 0.0014(7) O2B 0.0401(10) 0.0417(10) 0.0866(14) -0.0179(9) 0.0386(10) -0.0090(8) N1B 0.0362(11) 0.0415(12) 0.0809(16) -0.0195(11) 0.0333(11) -0.0085(10) C1B 0.0308(11) 0.0290(11) 0.0355(12) 0.0056(9) 0.0140(9) 0.0023(9) C2B 0.0389(13) 0.0354(13) 0.0534(15) 0.0017(11) 0.0256(11) 0.0008(11) C3B 0.0378(13) 0.0446(15) 0.0638(18) 0.0078(13) 0.0261(13) -0.0028(11) C4B 0.0377(13) 0.0363(13) 0.0516(16) 0.0062(11) 0.0127(11) -0.0083(11) C5B 0.0472(14) 0.0341(13) 0.0453(15) -0.0037(11) 0.0173(12) -0.0039(11) C6B 0.0366(12) 0.0345(12) 0.0409(13) 0.0005(10) 0.0184(10) -0.0002(10) C7B 0.0328(11) 0.0294(11) 0.0329(12) 0.0042(9) 0.0161(9) 0.0013(9) C8B 0.0361(12) 0.0316(12) 0.0553(15) -0.0073(11) 0.0240(11) -0.0022(10) C9B 0.0339(12) 0.0363(13) 0.0547(15) -0.0029(11) 0.0238(11) -0.0006(11) C10B 0.0363(13) 0.0402(13) 0.0472(14) -0.0062(11) 0.0231(11) -0.0080(11) C11B 0.0511(16) 0.0531(17) 0.128(3) -0.0291(17) 0.0477(17) -0.0154(14) C12B 0.060(2) 0.208(5) 0.066(2) -0.052(3) 0.0310(18) -0.046(3) C13B 0.084(3) 0.097(3) 0.162(4) 0.067(3) 0.079(3) 0.017(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 C7 1.250(3) . ? O2 C9 1.349(3) . ? O2 C11 1.441(3) . ? N1 C9 1.315(3) . ? N1 C10 1.465(3) . ? N1 H1 0.8800 . ? C1 C2 1.382(4) . ? C1 C6 1.391(3) . ? C1 C7 1.511(3) . ? C2 C3 1.390(4) . ? C2 H2 0.9500 . ? C3 C4 1.368(4) . ? C3 H3 0.9500 . ? C4 C5 1.363(5) . ? C4 H4 0.9500 . ? C5 C6 1.392(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.414(3) . ? C8 C9 1.374(3) . ? C8 H8 0.9500 . ? C10 C12 1.508(4) . ? C10 C13 1.525(4) . ? C10 C11 1.541(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O1A C7A 1.255(3) . ? O2A C9A 1.345(3) . ? O2A C11A 1.460(4) . ? N1A C9A 1.320(3) . ? N1A C10A 1.468(3) . ? N1A H1A 0.8800 . ? C1A C2A 1.386(3) . ? C1A C6A 1.394(3) . ? C1A C7A 1.495(3) . ? C2A C3A 1.383(4) . ? C2A H2A 0.9500 . ? C3A C4A 1.378(4) . ? C3A H3A 0.9500 . ? C4A C5A 1.378(4) . ? C4A H4A 0.9500 . ? C5A C6A 1.380(4) . ? C5A H5A 0.9500 . ? C6A H6A 0.9500 . ? C7A C8A 1.401(3) . ? C8A C9A 1.370(4) . ? C8A H8A 0.9500 . ? C10A C12A 1.499(4) . ? C10A C11A 1.506(4) . ? C10A C13A 1.520(4) . ? C11A H11C 0.9900 . ? C11A H11D 0.9900 . ? C12A H12D 0.9800 . ? C12A H12E 0.9800 . ? C12A H12F 0.9800 . ? C13A H13D 0.9800 . ? C13A H13E 0.9800 . ? C13A H13F 0.9800 . ? O1B C7B 1.256(3) . ? O2B C9B 1.351(3) . ? O2B C11B 1.443(3) . ? N1B C9B 1.321(3) . ? N1B C10B 1.457(3) . ? N1B H1B 0.8800 . ? C1B C6B 1.390(3) . ? C1B C2B 1.394(3) . ? C1B C7B 1.496(3) . ? C2B C3B 1.386(4) . ? C2B H2B 0.9500 . ? C3B C4B 1.384(4) . ? C3B H3B 0.9500 . ? C4B C5B 1.379(4) . ? C4B H4B 0.9500 . ? C5B C6B 1.384(3) . ? C5B H5B 0.9500 . ? C6B H6B 0.9500 . ? C7B C8B 1.414(3) . ? C8B C9B 1.373(3) . ? C8B H8B 0.9500 . ? C10B C12B 1.482(4) . ? C10B C11B 1.497(4) . ? C10B C13B 1.498(4) . ? C11B H11E 0.9900 . ? C11B H11F 0.9900 . ? C12B H12G 0.9800 . ? C12B H12H 0.9800 . ? C12B H12I 0.9800 . ? C13B H13G 0.9800 . ? C13B H13H 0.9800 . ? C13B H13I 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 C9 O2 C11 109.16(19) . . ? C9 N1 C10 113.7(2) . . ? C9 N1 H1 123.2 . . ? C10 N1 H1 123.1 . . ? C2 C1 C6 118.1(2) . . ? C2 C1 C7 118.6(2) . . ? C6 C1 C7 123.3(2) . . ? C1 C2 C3 120.9(3) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 120.2(3) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? O1 C7 C8 122.9(2) . . ? O1 C7 C1 117.9(2) . . ? C8 C7 C1 119.2(2) . . ? C9 C8 C7 122.2(2) . . ? C9 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? N1 C9 O2 110.5(2) . . ? N1 C9 C8 129.4(2) . . ? O2 C9 C8 120.1(2) . . ? N1 C10 C12 110.3(2) . . ? N1 C10 C13 109.3(2) . . ? C12 C10 C13 112.5(3) . . ? N1 C10 C11 98.94(19) . . ? C12 C10 C11 113.4(2) . . ? C13 C10 C11 111.6(2) . . ? O2 C11 C10 106.03(19) . . ? O2 C11 H11A 110.5 . . ? C10 C11 H11A 110.5 . . ? O2 C11 H11B 110.5 . . ? C10 C11 H11B 110.5 . . ? H11A C11 H11B 108.7 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9A O2A C11A 107.7(2) . . ? C9A N1A C10A 112.4(2) . . ? C9A N1A H1A 123.8 . . ? C10A N1A H1A 123.8 . . ? C2A C1A C6A 117.5(2) . . ? C2A C1A C7A 119.1(2) . . ? C6A C1A C7A 123.3(2) . . ? C3A C2A C1A 121.2(2) . . ? C3A C2A H2A 119.4 . . ? C1A C2A H2A 119.4 . . ? C4A C3A C2A 120.6(3) . . ? C4A C3A H3A 119.7 . . ? C2A C3A H3A 119.7 . . ? C5A C4A C3A 118.8(3) . . ? C5A C4A H4A 120.6 . . ? C3A C4A H4A 120.6 . . ? C4A C5A C6A 120.7(3) . . ? C4A C5A H5A 119.6 . . ? C6A C5A H5A 119.6 . . ? C5A C6A C1A 121.1(2) . . ? C5A C6A H6A 119.5 . . ? C1A C6A H6A 119.5 . . ? O1A C7A C8A 121.7(2) . . ? O1A C7A C1A 118.6(2) . . ? C8A C7A C1A 119.7(2) . . ? C9A C8A C7A 120.7(2) . . ? C9A C8A H8A 119.7 . . ? C7A C8A H8A 119.7 . . ? N1A C9A O2A 110.2(2) . . ? N1A C9A C8A 127.8(2) . . ? O2A C9A C8A 121.9(2) . . ? N1A C10A C12A 109.9(2) . . ? N1A C10A C11A 98.8(2) . . ? C12A C10A C11A 113.7(3) . . ? N1A C10A C13A 111.1(2) . . ? C12A C10A C13A 110.4(3) . . ? C11A C10A C13A 112.5(3) . . ? O2A C11A C10A 105.2(2) . . ? O2A C11A H11C 110.7 . . ? C10A C11A H11C 110.7 . . ? O2A C11A H11D 110.7 . . ? C10A C11A H11D 110.7 . . ? H11C C11A H11D 108.8 . . ? C10A C12A H12D 109.5 . . ? C10A C12A H12E 109.5 . . ? H12D C12A H12E 109.5 . . ? C10A C12A H12F 109.5 . . ? H12D C12A H12F 109.5 . . ? H12E C12A H12F 109.5 . . ? C10A C13A H13D 109.5 . . ? C10A C13A H13E 109.5 . . ? H13D C13A H13E 109.5 . . ? C10A C13A H13F 109.5 . . ? H13D C13A H13F 109.5 . . ? H13E C13A H13F 109.5 . . ? C9B O2B C11B 108.2(2) . . ? C9B N1B C10B 112.7(2) . . ? C9B N1B H1B 123.6 . . ? C10B N1B H1B 123.6 . . ? C6B C1B C2B 118.6(2) . . ? C6B C1B C7B 123.2(2) . . ? C2B C1B C7B 118.2(2) . . ? C3B C2B C1B 120.7(2) . . ? C3B C2B H2B 119.6 . . ? C1B C2B H2B 119.6 . . ? C4B C3B C2B 120.1(2) . . ? C4B C3B H3B 119.9 . . ? C2B C3B H3B 119.9 . . ? C5B C4B C3B 119.4(2) . . ? C5B C4B H4B 120.3 . . ? C3B C4B H4B 120.3 . . ? C4B C5B C6B 120.7(2) . . ? C4B C5B H5B 119.6 . . ? C6B C5B H5B 119.6 . . ? C5B C6B C1B 120.4(2) . . ? C5B C6B H6B 119.8 . . ? C1B C6B H6B 119.8 . . ? O1B C7B C8B 122.5(2) . . ? O1B C7B C1B 118.00(19) . . ? C8B C7B C1B 119.5(2) . . ? C9B C8B C7B 120.9(2) . . ? C9B C8B H8B 119.6 . . ? C7B C8B H8B 119.6 . . ? N1B C9B O2B 110.6(2) . . ? N1B C9B C8B 129.6(2) . . ? O2B C9B C8B 119.8(2) . . ? N1B C10B C12B 111.7(2) . . ? N1B C10B C11B 100.5(2) . . ? C12B C10B C11B 114.5(3) . . ? N1B C10B C13B 108.0(2) . . ? C12B C10B C13B 110.5(4) . . ? C11B C10B C13B 111.2(3) . . ? O2B C11B C10B 106.9(2) . . ? O2B C11B H11E 110.3 . . ? C10B C11B H11E 110.3 . . ? O2B C11B H11F 110.3 . . ? C10B C11B H11F 110.3 . . ? H11E C11B H11F 108.6 . . ? C10B C12B H12G 109.5 . . ? C10B C12B H12H 109.5 . . ? H12G C12B H12H 109.5 . . ? C10B C12B H12I 109.5 . . ? H12G C12B H12I 109.5 . . ? H12H C12B H12I 109.5 . . ? C10B C13B H13G 109.5 . . ? C10B C13B H13H 109.5 . . ? H13G C13B H13H 109.5 . . ? C10B C13B H13I 109.5 . . ? H13G C13B H13I 109.5 . . ? H13H C13B H13I 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.8(4) . . . . ? C7 C1 C2 C3 179.8(2) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C2 C3 C4 C5 -0.9(5) . . . . ? C3 C4 C5 C6 0.6(5) . . . . ? C2 C1 C6 C5 -1.1(4) . . . . ? C7 C1 C6 C5 179.9(3) . . . . ? C4 C5 C6 C1 0.4(5) . . . . ? C2 C1 C7 O1 1.2(3) . . . . ? C6 C1 C7 O1 -179.8(2) . . . . ? C2 C1 C7 C8 -176.8(2) . . . . ? C6 C1 C7 C8 2.2(3) . . . . ? O1 C7 C8 C9 -3.8(4) . . . . ? C1 C7 C8 C9 174.0(2) . . . . ? C10 N1 C9 O2 7.3(3) . . . . ? C10 N1 C9 C8 -172.0(3) . . . . ? C11 O2 C9 N1 1.8(3) . . . . ? C11 O2 C9 C8 -178.8(2) . . . . ? C7 C8 C9 N1 -1.1(4) . . . . ? C7 C8 C9 O2 179.7(2) . . . . ? C9 N1 C10 C12 -131.2(2) . . . . ? C9 N1 C10 C13 104.6(3) . . . . ? C9 N1 C10 C11 -12.1(3) . . . . ? C9 O2 C11 C10 -9.3(3) . . . . ? N1 C10 C11 O2 12.1(3) . . . . ? C12 C10 C11 O2 128.9(3) . . . . ? C13 C10 C11 O2 -102.8(3) . . . . ? C6A C1A C2A C3A 0.1(4) . . . . ? C7A C1A C2A C3A -177.6(2) . . . . ? C1A C2A C3A C4A 0.8(4) . . . . ? C2A C3A C4A C5A -1.0(4) . . . . ? C3A C4A C5A C6A 0.3(4) . . . . ? C4A C5A C6A C1A 0.6(4) . . . . ? C2A C1A C6A C5A -0.8(4) . . . . ? C7A C1A C6A C5A 176.8(2) . . . . ? C2A C1A C7A O1A 2.4(3) . . . . ? C6A C1A C7A O1A -175.2(2) . . . . ? C2A C1A C7A C8A -176.9(2) . . . . ? C6A C1A C7A C8A 5.5(4) . . . . ? O1A C7A C8A C9A 7.3(4) . . . . ? C1A C7A C8A C9A -173.4(2) . . . . ? C10A N1A C9A O2A -9.5(3) . . . . ? C10A N1A C9A C8A 169.1(3) . . . . ? C11A O2A C9A N1A -6.9(4) . . . . ? C11A O2A C9A C8A 174.4(3) . . . . ? C7A C8A C9A N1A -2.8(5) . . . . ? C7A C8A C9A O2A 175.6(3) . . . . ? C9A N1A C10A C12A -98.8(3) . . . . ? C9A N1A C10A C11A 20.4(3) . . . . ? C9A N1A C10A C13A 138.8(3) . . . . ? C9A O2A C11A C10A 19.7(4) . . . . ? N1A C10A C11A O2A -22.8(4) . . . . ? C12A C10A C11A O2A 93.5(4) . . . . ? C13A C10A C11A O2A -140.1(3) . . . . ? C6B C1B C2B C3B -0.1(4) . . . . ? C7B C1B C2B C3B -179.7(2) . . . . ? C1B C2B C3B C4B -0.2(4) . . . . ? C2B C3B C4B C5B 0.4(4) . . . . ? C3B C4B C5B C6B -0.3(4) . . . . ? C4B C5B C6B C1B 0.0(4) . . . . ? C2B C1B C6B C5B 0.2(3) . . . . ? C7B C1B C6B C5B 179.7(2) . . . . ? C6B C1B C7B O1B 165.1(2) . . . . ? C2B C1B C7B O1B -15.4(3) . . . . ? C6B C1B C7B C8B -15.4(3) . . . . ? C2B C1B C7B C8B 164.1(2) . . . . ? O1B C7B C8B C9B 4.1(4) . . . . ? C1B C7B C8B C9B -175.3(2) . . . . ? C10B N1B C9B O2B 5.4(3) . . . . ? C10B N1B C9B C8B -175.8(3) . . . . ? C11B O2B C9B N1B 2.1(3) . . . . ? C11B O2B C9B C8B -176.9(3) . . . . ? C7B C8B C9B N1B 2.2(4) . . . . ? C7B C8B C9B O2B -179.1(2) . . . . ? C9B N1B C10B C12B -131.7(3) . . . . ? C9B N1B C10B C11B -9.9(3) . . . . ? C9B N1B C10B C13B 106.6(3) . . . . ? C9B O2B C11B C10B -8.3(4) . . . . ? N1B C10B C11B O2B 10.5(3) . . . . ? C12B C10B C11B O2B 130.3(3) . . . . ? C13B C10B C11B O2B -103.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1B 0.88 2.15 2.893(3) 141.3 4_576 N1 H1 O1 0.88 2.23 2.770(3) 119.3 . N1A H1A O1A 0.88 2.10 2.647(3) 119.1 . N1B H1B O1B 0.88 2.19 2.722(3) 118.6 . N1B H1B O1 0.88 2.19 2.967(3) 147.4 4_575 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.535 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.045 data_1178 _database_code_depnum_ccdc_archive 'CCDC 799950' #TrackingRef '- 799950.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N2 O4' _chemical_formula_sum 'C13 H14 N2 O4' _chemical_formula_weight 262.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.1245(3) _cell_length_b 14.0624(3) _cell_length_c 16.2235(4) _cell_angle_alpha 83.164(2) _cell_angle_beta 73.727(2) _cell_angle_gamma 69.797(2) _cell_volume 2491.16(11) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6094 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 35976 _diffrn_reflns_av_R_equivalents 0.0640 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.43 _reflns_number_total 11295 _reflns_number_gt 6852 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0605P)^2^+0.6843P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0065(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 11295 _refine_ls_number_parameters 709 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1043 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1510 _refine_ls_wR_factor_gt 0.1256 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.66141(16) 1.04603(11) 0.19897(11) 0.0470(4) Uani 1 1 d . . . O2 O 0.52108(13) 0.90232(10) 0.06375(9) 0.0348(3) Uani 1 1 d . . . O3 O 0.51231(16) 0.42215(12) 0.18374(12) 0.0524(5) Uani 1 1 d . . . O4 O 0.69791(15) 0.37697(11) 0.19132(11) 0.0463(4) Uani 1 1 d . . . N1 N 0.55797(15) 1.07038(12) 0.10191(11) 0.0300(4) Uani 1 1 d . . . H1 H 0.5239 1.0558 0.0660 0.036 Uiso 1 1 calc R A . N2 N 0.60396(17) 0.44167(13) 0.18199(11) 0.0335(4) Uani 1 1 d . . . C1 C 0.59221(17) 0.74627(14) 0.13612(12) 0.0255(4) Uani 1 1 d . . . C2 C 0.48781(18) 0.72049(15) 0.14575(13) 0.0289(4) Uani 1 1 d . . . H2 H 0.4141 0.7715 0.1410 0.035 Uiso 1 1 calc R . . C3 C 0.49159(18) 0.62071(15) 0.16215(13) 0.0298(4) Uani 1 1 d . . . H3 H 0.4208 0.6027 0.1691 0.036 Uiso 1 1 calc R . . C4 C 0.59997(18) 0.54776(14) 0.16820(12) 0.0267(4) Uani 1 1 d . . . C5 C 0.70417(18) 0.57089(15) 0.16088(14) 0.0313(5) Uani 1 1 d . . . H5 H 0.7773 0.5195 0.1663 0.038 Uiso 1 1 calc R . . C6 C 0.69916(18) 0.67094(14) 0.14543(14) 0.0303(5) Uani 1 1 d . . . H6 H 0.7695 0.6887 0.1411 0.036 Uiso 1 1 calc R . . C7 C 0.58461(17) 0.85491(14) 0.11402(13) 0.0269(4) Uani 1 1 d . A . C8 C 0.64351(19) 0.89827(15) 0.15486(14) 0.0329(5) Uani 1 1 d . . . H8 H 0.6985 0.8563 0.1865 0.039 Uiso 1 1 calc R A . C9 C 0.62141(19) 1.00201(15) 0.14901(13) 0.0318(5) Uani 1 1 d . A . C10 C 0.55091(18) 1.17381(14) 0.11662(13) 0.0305(4) Uani 1 1 d D A . C11 C 0.5916(3) 1.15442(19) 0.19923(19) 0.0376(7) Uani 0.813(5) 1 d P A 1 H11A H 0.6429 1.1957 0.2000 0.045 Uiso 0.813(5) 1 calc PR A 1 H11B H 0.5206 1.1708 0.2499 0.045 Uiso 0.813(5) 1 calc PR A 1 C12 C 0.4247(3) 1.2471(2) 0.1230(3) 0.0492(9) Uani 0.813(5) 1 d P A 1 H12A H 0.4026 1.2481 0.0691 0.074 Uiso 0.813(5) 1 calc PR A 1 H12B H 0.4223 1.3151 0.1334 0.074 Uiso 0.813(5) 1 calc PR A 1 H12C H 0.3670 1.2259 0.1705 0.074 Uiso 0.813(5) 1 calc PR A 1 C13 C 0.6452(3) 1.2039(2) 0.04386(16) 0.0399(8) Uani 0.813(5) 1 d PD A 1 H13A H 0.7263 1.1553 0.0424 0.060 Uiso 0.813(5) 1 calc PR A 1 H13B H 0.6434 1.2719 0.0536 0.060 Uiso 0.813(5) 1 calc PR A 1 H13C H 0.6263 1.2037 -0.0110 0.060 Uiso 0.813(5) 1 calc PR A 1 C11A C 0.6510(11) 1.1542(10) 0.1619(10) 0.045(4) Uiso 0.187(5) 1 d PD A 2 H11C H 0.6271 1.2032 0.2079 0.054 Uiso 0.187(5) 1 calc PR A 2 H11D H 0.7280 1.1565 0.1210 0.054 Uiso 0.187(5) 1 calc PR A 2 C12A C 0.4297(7) 1.2123(10) 0.1837(7) 0.048(4) Uiso 0.187(5) 1 d PD A 2 H12D H 0.3639 1.2107 0.1605 0.072 Uiso 0.187(5) 1 calc PR A 2 H12E H 0.4156 1.2820 0.1980 0.072 Uiso 0.187(5) 1 calc PR A 2 H12F H 0.4318 1.1689 0.2356 0.072 Uiso 0.187(5) 1 calc PR A 2 C13A C 0.5485(13) 1.2509(10) 0.0446(9) 0.046(4) Uiso 0.187(5) 1 d P A 2 H13D H 0.6236 1.2277 -0.0012 0.069 Uiso 0.187(5) 1 calc PR A 2 H13E H 0.5417 1.3156 0.0658 0.069 Uiso 0.187(5) 1 calc PR A 2 H13F H 0.4785 1.2598 0.0219 0.069 Uiso 0.187(5) 1 calc PR A 2 O21 O -0.01455(13) 0.69806(10) 0.09556(10) 0.0337(3) Uani 1 1 d . . . O22 O 0.19480(12) 0.83692(10) 0.16658(9) 0.0321(3) Uani 1 1 d . . . O23 O 0.15324(16) 1.32947(12) 0.05425(12) 0.0517(5) Uani 1 1 d . . . O24 O -0.04232(16) 1.37055(11) 0.09051(12) 0.0487(4) Uani 1 1 d . . . N21 N 0.13624(14) 0.67396(11) 0.15447(11) 0.0280(4) Uani 1 1 d . . . H21 H 0.1780 0.6886 0.1846 0.034 Uiso 1 1 calc R . . N22 N 0.05998(18) 1.30734(13) 0.07630(11) 0.0343(4) Uani 1 1 d . . . C21 C 0.09177(17) 0.99788(14) 0.11481(12) 0.0255(4) Uani 1 1 d . . . C22 C 0.19584(18) 1.02697(15) 0.09165(12) 0.0280(4) Uani 1 1 d . . . H22 H 0.2737 0.9771 0.0861 0.034 Uiso 1 1 calc R . . C23 C 0.18574(19) 1.12849(15) 0.07677(13) 0.0298(4) Uani 1 1 d . . . H23 H 0.2560 1.1489 0.0598 0.036 Uiso 1 1 calc R . . C24 C 0.07091(18) 1.19908(14) 0.08729(12) 0.0277(4) Uani 1 1 d . . . C25 C -0.03398(18) 1.17351(15) 0.10997(13) 0.0310(5) Uani 1 1 d . . . H25 H -0.1116 1.2241 0.1168 0.037 Uiso 1 1 calc R . . C26 C -0.02238(18) 1.07120(14) 0.12250(13) 0.0302(4) Uani 1 1 d . . . H26 H -0.0928 1.0512 0.1364 0.036 Uiso 1 1 calc R . . C27 C 0.10791(17) 0.88718(14) 0.13469(13) 0.0271(4) Uani 1 1 d . . . C28 C 0.02818(18) 0.84578(14) 0.11493(13) 0.0288(4) Uani 1 1 d . . . H28 H -0.0405 0.8887 0.0961 0.035 Uiso 1 1 calc R . . C29 C 0.05051(17) 0.74254(14) 0.12309(13) 0.0265(4) Uani 1 1 d . . . C30 C 0.15315(17) 0.57029(14) 0.13278(13) 0.0268(4) Uani 1 1 d . . . C31 C 0.02742(19) 0.59046(15) 0.11826(15) 0.0338(5) Uani 1 1 d . . . H31A H 0.0331 0.5488 0.0712 0.041 Uiso 1 1 calc R . . H31B H -0.0287 0.5746 0.1711 0.041 Uiso 1 1 calc R . . C32 C 0.17808(19) 0.49514(15) 0.20575(14) 0.0325(5) Uani 1 1 d . . . H32A H 0.2551 0.4913 0.2165 0.049 Uiso 1 1 calc R . . H32B H 0.1832 0.4282 0.1903 0.049 Uiso 1 1 calc R . . H32C H 0.1120 0.5173 0.2577 0.049 Uiso 1 1 calc R . . C33 C 0.2544(2) 0.53961(16) 0.05027(14) 0.0365(5) Uani 1 1 d . . . H33A H 0.2343 0.5885 0.0040 0.055 Uiso 1 1 calc R . . H33B H 0.2626 0.4720 0.0343 0.055 Uiso 1 1 calc R . . H33C H 0.3312 0.5387 0.0596 0.055 Uiso 1 1 calc R . . O41 O 0.23842(13) 0.55333(10) 0.65508(10) 0.0364(4) Uani 1 1 d . . . O42 O 0.03257(12) 0.41551(10) 0.58013(9) 0.0311(3) Uani 1 1 d . . . O43 O 0.06602(15) -0.07506(12) 0.67109(11) 0.0456(4) Uani 1 1 d . . . O44 O 0.25814(16) -0.11877(11) 0.66008(13) 0.0515(5) Uani 1 1 d . . . N41 N 0.09011(14) 0.57700(11) 0.59389(11) 0.0278(4) Uani 1 1 d . . . H41 H 0.0490 0.5620 0.5633 0.033 Uiso 1 1 calc R . . N42 N 0.15933(17) -0.05478(12) 0.66240(11) 0.0322(4) Uani 1 1 d . . . C41 C 0.13318(16) 0.25386(14) 0.63067(12) 0.0234(4) Uani 1 1 d . . . C42 C 0.02884(17) 0.22602(14) 0.64914(12) 0.0260(4) Uani 1 1 d . . . H42 H -0.0483 0.2767 0.6535 0.031 Uiso 1 1 calc R . . C43 C 0.03713(17) 0.12470(14) 0.66110(12) 0.0265(4) Uani 1 1 d . . . H43 H -0.0336 0.1052 0.6744 0.032 Uiso 1 1 calc R . . C44 C 0.15076(18) 0.05294(13) 0.65311(12) 0.0256(4) Uani 1 1 d . . . C45 C 0.25621(18) 0.07766(14) 0.63580(13) 0.0290(4) Uani 1 1 d . . . H45 H 0.3332 0.0265 0.6310 0.035 Uiso 1 1 calc R . . C46 C 0.24586(17) 0.17944(14) 0.62576(13) 0.0277(4) Uani 1 1 d . . . H46 H 0.3165 0.1986 0.6154 0.033 Uiso 1 1 calc R . . C47 C 0.11772(17) 0.36446(13) 0.61304(12) 0.0250(4) Uani 1 1 d . . . C48 C 0.19623(18) 0.40538(14) 0.63548(13) 0.0291(4) Uani 1 1 d . . . H48 H 0.2631 0.3626 0.6564 0.035 Uiso 1 1 calc R . . C49 C 0.17423(17) 0.50900(14) 0.62654(13) 0.0278(4) Uani 1 1 d . . . C50 C 0.07339(18) 0.68116(14) 0.61494(13) 0.0263(4) Uani 1 1 d . . . C51 C 0.1974(2) 0.66123(15) 0.63138(15) 0.0362(5) Uani 1 1 d . . . H51A H 0.2548 0.6765 0.5791 0.043 Uiso 1 1 calc R . . H51B H 0.1903 0.7033 0.6786 0.043 Uiso 1 1 calc R . . C52 C -0.0301(2) 0.71379(16) 0.69572(14) 0.0369(5) Uani 1 1 d . . . H52A H -0.1064 0.7158 0.6847 0.055 Uiso 1 1 calc R . . H52B H -0.0376 0.7813 0.7115 0.055 Uiso 1 1 calc R . . H52C H -0.0129 0.6652 0.7428 0.055 Uiso 1 1 calc R . . C53 C 0.05128(19) 0.75417(15) 0.54038(14) 0.0331(5) Uani 1 1 d . . . H53A H 0.1179 0.7300 0.4891 0.050 Uiso 1 1 calc R . . H53B H 0.0474 0.8213 0.5544 0.050 Uiso 1 1 calc R . . H53C H -0.0257 0.7585 0.5293 0.050 Uiso 1 1 calc R . . O61 O 0.46246(13) 0.80204(10) 0.40843(10) 0.0361(4) Uani 1 1 d . . . O62 O 0.26317(12) 0.65978(10) 0.33051(9) 0.0305(3) Uani 1 1 d . . . O63 O 0.30181(16) 0.16850(12) 0.41290(12) 0.0521(5) Uani 1 1 d . . . O64 O 0.47955(15) 0.12907(11) 0.43482(11) 0.0467(4) Uani 1 1 d . . . N61 N 0.32023(15) 0.82302(12) 0.34156(11) 0.0290(4) Uani 1 1 d . . . H61 H 0.2815 0.8066 0.3099 0.035 Uiso 1 1 calc R . . N62 N 0.38725(17) 0.19137(13) 0.42063(11) 0.0324(4) Uani 1 1 d . . . C61 C 0.35948(16) 0.50009(14) 0.38716(12) 0.0241(4) Uani 1 1 d . . . C62 C 0.25806(17) 0.47090(15) 0.39688(12) 0.0273(4) Uani 1 1 d . . . H62 H 0.1823 0.5208 0.3951 0.033 Uiso 1 1 calc R . . C63 C 0.26641(18) 0.36983(15) 0.40910(13) 0.0289(4) Uani 1 1 d . . . H63 H 0.1973 0.3497 0.4154 0.035 Uiso 1 1 calc R . . C64 C 0.37737(18) 0.29889(14) 0.41194(12) 0.0261(4) Uani 1 1 d . . . C65 C 0.47941(18) 0.32526(15) 0.40515(14) 0.0316(5) Uani 1 1 d . . . H65 H 0.5544 0.2751 0.4086 0.038 Uiso 1 1 calc R . . C66 C 0.46937(18) 0.42695(14) 0.39321(14) 0.0308(5) Uani 1 1 d . . . H66 H 0.5380 0.4470 0.3891 0.037 Uiso 1 1 calc R . . C67 C 0.34518(17) 0.61053(14) 0.36679(13) 0.0263(4) Uani 1 1 d . . . C68 C 0.42111(18) 0.65310(14) 0.39045(13) 0.0296(4) Uani 1 1 d . . . H68 H 0.4855 0.6114 0.4144 0.036 Uiso 1 1 calc R . . C69 C 0.40094(17) 0.75636(14) 0.37848(13) 0.0281(4) Uani 1 1 d . . . C70 C 0.30323(17) 0.92811(14) 0.36001(13) 0.0269(4) Uani 1 1 d . . . C71 C 0.42375(19) 0.90896(15) 0.38238(15) 0.0346(5) Uani 1 1 d . . . H71A H 0.4848 0.9230 0.3319 0.042 Uiso 1 1 calc R . . H71B H 0.4123 0.9525 0.4298 0.042 Uiso 1 1 calc R . . C72 C 0.1947(2) 0.96465(16) 0.43699(14) 0.0366(5) Uani 1 1 d . . . H72A H 0.1204 0.9675 0.4225 0.055 Uiso 1 1 calc R . . H72B H 0.1876 1.0323 0.4521 0.055 Uiso 1 1 calc R . . H72C H 0.2064 0.9176 0.4859 0.055 Uiso 1 1 calc R . . C73 C 0.2886(2) 0.99767(15) 0.28233(14) 0.0346(5) Uani 1 1 d . . . H73A H 0.3583 0.9708 0.2334 0.052 Uiso 1 1 calc R . . H73B H 0.2846 1.0654 0.2950 0.052 Uiso 1 1 calc R . . H73C H 0.2136 1.0019 0.2682 0.052 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 0.0728(12) 0.0293(8) 0.0539(11) 0.0037(7) -0.0410(9) -0.0169(8) O2 0.0406(8) 0.0294(8) 0.0385(9) 0.0065(6) -0.0201(7) -0.0110(6) O3 0.0517(11) 0.0399(9) 0.0773(13) -0.0007(8) -0.0201(9) -0.0267(8) O4 0.0483(10) 0.0250(8) 0.0651(12) 0.0008(7) -0.0207(9) -0.0072(7) N1 0.0364(9) 0.0225(8) 0.0350(10) -0.0024(7) -0.0155(8) -0.0088(7) N2 0.0406(10) 0.0285(9) 0.0332(10) -0.0033(7) -0.0090(8) -0.0133(8) C1 0.0264(10) 0.0242(10) 0.0243(10) -0.0015(7) -0.0065(8) -0.0059(8) C2 0.0254(10) 0.0292(10) 0.0304(11) 0.0000(8) -0.0084(8) -0.0061(8) C3 0.0267(10) 0.0335(11) 0.0312(11) -0.0020(8) -0.0072(8) -0.0119(9) C4 0.0328(11) 0.0232(10) 0.0240(10) -0.0030(7) -0.0062(8) -0.0092(8) C5 0.0267(10) 0.0251(10) 0.0404(12) -0.0012(8) -0.0100(9) -0.0050(8) C6 0.0248(10) 0.0267(10) 0.0412(12) -0.0010(8) -0.0108(9) -0.0086(8) C7 0.0242(10) 0.0240(10) 0.0284(11) -0.0003(8) -0.0040(8) -0.0051(8) C8 0.0369(12) 0.0251(10) 0.0394(12) 0.0037(8) -0.0181(10) -0.0086(9) C9 0.0373(11) 0.0309(11) 0.0304(11) -0.0003(8) -0.0141(9) -0.0112(9) C10 0.0365(11) 0.0217(10) 0.0364(12) -0.0026(8) -0.0119(9) -0.0109(9) C11 0.0565(19) 0.0260(14) 0.0318(15) -0.0025(11) -0.0142(15) -0.0124(13) C12 0.0370(16) 0.0285(15) 0.082(3) -0.0125(15) -0.0193(16) -0.0042(12) C13 0.0543(19) 0.0379(16) 0.0345(16) 0.0022(12) -0.0120(13) -0.0243(14) O21 0.0370(8) 0.0232(7) 0.0485(9) 0.0038(6) -0.0229(7) -0.0113(6) O22 0.0264(7) 0.0251(7) 0.0450(9) 0.0021(6) -0.0121(6) -0.0074(6) O23 0.0572(11) 0.0335(9) 0.0723(13) 0.0040(8) -0.0173(9) -0.0260(8) O24 0.0512(10) 0.0245(8) 0.0635(12) -0.0039(7) -0.0137(9) -0.0036(7) N21 0.0290(9) 0.0213(8) 0.0375(10) -0.0008(7) -0.0149(7) -0.0078(7) N22 0.0478(11) 0.0242(9) 0.0337(10) -0.0009(7) -0.0134(8) -0.0130(8) C21 0.0302(10) 0.0225(10) 0.0237(10) -0.0004(7) -0.0078(8) -0.0080(8) C22 0.0281(10) 0.0270(10) 0.0273(11) -0.0019(8) -0.0071(8) -0.0068(8) C23 0.0341(11) 0.0305(11) 0.0283(11) -0.0004(8) -0.0079(9) -0.0149(9) C24 0.0371(11) 0.0233(10) 0.0245(10) -0.0001(7) -0.0108(8) -0.0100(8) C25 0.0289(10) 0.0244(10) 0.0376(12) -0.0021(8) -0.0110(9) -0.0039(8) C26 0.0276(10) 0.0268(10) 0.0355(12) -0.0015(8) -0.0086(9) -0.0074(8) C27 0.0246(10) 0.0231(10) 0.0304(11) 0.0000(8) -0.0053(8) -0.0053(8) C28 0.0287(10) 0.0240(10) 0.0347(11) 0.0010(8) -0.0128(9) -0.0067(8) C29 0.0240(10) 0.0265(10) 0.0312(11) -0.0017(8) -0.0092(8) -0.0092(8) C30 0.0281(10) 0.0231(10) 0.0312(11) -0.0002(8) -0.0086(8) -0.0103(8) C31 0.0370(12) 0.0238(10) 0.0452(13) 0.0042(9) -0.0165(10) -0.0125(9) C32 0.0345(11) 0.0251(10) 0.0367(12) 0.0041(8) -0.0101(9) -0.0091(9) C33 0.0404(12) 0.0328(11) 0.0349(12) -0.0035(9) -0.0046(10) -0.0135(10) O41 0.0389(8) 0.0257(7) 0.0554(10) 0.0050(6) -0.0286(7) -0.0126(6) O42 0.0239(7) 0.0247(7) 0.0450(9) 0.0023(6) -0.0148(6) -0.0046(6) O43 0.0500(10) 0.0365(9) 0.0599(11) 0.0028(7) -0.0172(8) -0.0247(8) O44 0.0505(10) 0.0230(8) 0.0843(14) -0.0017(8) -0.0312(10) -0.0050(7) N41 0.0292(9) 0.0203(8) 0.0367(10) -0.0022(7) -0.0148(7) -0.0061(7) N42 0.0427(11) 0.0250(9) 0.0326(10) -0.0013(7) -0.0150(8) -0.0113(8) C41 0.0236(9) 0.0223(9) 0.0252(10) -0.0020(7) -0.0090(8) -0.0059(8) C42 0.0221(9) 0.0265(10) 0.0294(11) -0.0028(8) -0.0088(8) -0.0055(8) C43 0.0267(10) 0.0297(10) 0.0263(10) 0.0003(8) -0.0077(8) -0.0129(8) C44 0.0350(11) 0.0197(9) 0.0248(10) -0.0001(7) -0.0116(8) -0.0095(8) C45 0.0263(10) 0.0229(10) 0.0370(12) -0.0020(8) -0.0129(9) -0.0028(8) C46 0.0231(10) 0.0271(10) 0.0334(11) -0.0012(8) -0.0084(8) -0.0079(8) C47 0.0218(9) 0.0204(9) 0.0291(11) -0.0001(7) -0.0059(8) -0.0030(7) C48 0.0290(10) 0.0224(10) 0.0380(12) 0.0010(8) -0.0152(9) -0.0062(8) C49 0.0270(10) 0.0262(10) 0.0324(11) -0.0009(8) -0.0099(8) -0.0096(8) C50 0.0309(10) 0.0207(9) 0.0304(11) 0.0007(7) -0.0107(8) -0.0103(8) C51 0.0388(12) 0.0235(10) 0.0527(14) 0.0053(9) -0.0221(11) -0.0121(9) C52 0.0444(13) 0.0340(11) 0.0335(12) -0.0056(9) -0.0038(10) -0.0176(10) C53 0.0378(12) 0.0271(10) 0.0357(12) 0.0022(8) -0.0113(9) -0.0116(9) O61 0.0395(8) 0.0253(7) 0.0532(10) 0.0037(6) -0.0263(7) -0.0127(6) O62 0.0251(7) 0.0239(7) 0.0437(9) 0.0009(6) -0.0149(6) -0.0050(6) O63 0.0613(11) 0.0359(9) 0.0770(13) 0.0045(8) -0.0324(10) -0.0281(8) O64 0.0479(10) 0.0254(8) 0.0647(12) 0.0013(7) -0.0173(9) -0.0077(7) N61 0.0297(9) 0.0223(8) 0.0375(10) -0.0033(7) -0.0139(7) -0.0065(7) N62 0.0408(10) 0.0259(9) 0.0323(10) -0.0020(7) -0.0105(8) -0.0117(8) C61 0.0229(9) 0.0242(9) 0.0243(10) -0.0036(7) -0.0057(8) -0.0059(8) C62 0.0226(10) 0.0282(10) 0.0296(11) -0.0025(8) -0.0066(8) -0.0059(8) C63 0.0276(10) 0.0315(11) 0.0316(11) -0.0010(8) -0.0089(8) -0.0132(8) C64 0.0323(11) 0.0228(10) 0.0246(10) -0.0033(7) -0.0079(8) -0.0093(8) C65 0.0267(10) 0.0239(10) 0.0427(13) -0.0019(8) -0.0130(9) -0.0029(8) C66 0.0243(10) 0.0252(10) 0.0438(13) -0.0011(8) -0.0102(9) -0.0081(8) C67 0.0210(9) 0.0239(10) 0.0308(11) -0.0017(8) -0.0045(8) -0.0048(8) C68 0.0255(10) 0.0242(10) 0.0393(12) -0.0004(8) -0.0133(9) -0.0045(8) C69 0.0270(10) 0.0260(10) 0.0329(11) -0.0014(8) -0.0105(8) -0.0083(8) C70 0.0283(10) 0.0213(9) 0.0337(11) -0.0020(8) -0.0108(8) -0.0088(8) C71 0.0358(12) 0.0241(10) 0.0487(14) 0.0036(9) -0.0167(10) -0.0125(9) C72 0.0385(12) 0.0340(11) 0.0364(12) -0.0057(9) -0.0033(9) -0.0139(10) C73 0.0398(12) 0.0297(11) 0.0364(12) 0.0039(9) -0.0134(10) -0.0123(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.350(2) . ? O1 C11 1.466(3) . ? O1 C11A 1.544(14) . ? O2 C7 1.253(2) . ? O3 N2 1.226(2) . ? O4 N2 1.223(2) . ? N1 C9 1.321(3) . ? N1 C10 1.471(2) . ? N1 H1 0.8800 . ? N2 C4 1.468(2) . ? C1 C6 1.396(3) . ? C1 C2 1.397(3) . ? C1 C7 1.504(3) . ? C2 C3 1.384(3) . ? C2 H2 0.9500 . ? C3 C4 1.381(3) . ? C3 H3 0.9500 . ? C4 C5 1.381(3) . ? C5 C6 1.382(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.408(3) . ? C8 C9 1.386(3) . ? C8 H8 0.9500 . ? C10 C13A 1.496(13) . ? C10 C12 1.504(3) . ? C10 C11 1.518(3) . ? C10 C11A 1.519(3) . ? C10 C12A 1.527(3) . ? C10 C13 1.529(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C11A H11C 0.9900 . ? C11A H11D 0.9900 . ? C12A H12D 0.9800 . ? C12A H12E 0.9800 . ? C12A H12F 0.9800 . ? C13A H13D 0.9800 . ? C13A H13E 0.9800 . ? C13A H13F 0.9800 . ? O21 C29 1.348(2) . ? O21 C31 1.458(2) . ? O22 C27 1.257(2) . ? O23 N22 1.222(2) . ? O24 N22 1.228(2) . ? N21 C29 1.325(2) . ? N21 C30 1.472(2) . ? N21 H21 0.8800 . ? N22 C24 1.475(2) . ? C21 C26 1.394(3) . ? C21 C22 1.398(3) . ? C21 C27 1.507(3) . ? C22 C23 1.388(3) . ? C22 H22 0.9500 . ? C23 C24 1.380(3) . ? C23 H23 0.9500 . ? C24 C25 1.380(3) . ? C25 C26 1.392(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.408(3) . ? C28 C29 1.379(3) . ? C28 H28 0.9500 . ? C30 C32 1.514(3) . ? C30 C33 1.528(3) . ? C30 C31 1.532(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? O41 C49 1.347(2) . ? O41 C51 1.464(2) . ? O42 C47 1.254(2) . ? O43 N42 1.227(2) . ? O44 N42 1.219(2) . ? N41 C49 1.321(2) . ? N41 C50 1.476(2) . ? N41 H41 0.8800 . ? N42 C44 1.474(2) . ? C41 C46 1.393(3) . ? C41 C42 1.395(3) . ? C41 C47 1.503(2) . ? C42 C43 1.387(3) . ? C42 H42 0.9500 . ? C43 C44 1.380(3) . ? C43 H43 0.9500 . ? C44 C45 1.384(3) . ? C45 C46 1.387(3) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 C48 1.411(3) . ? C48 C49 1.385(3) . ? C48 H48 0.9500 . ? C50 C53 1.512(3) . ? C50 C51 1.525(3) . ? C50 C52 1.525(3) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? O61 C69 1.347(2) . ? O61 C71 1.460(2) . ? O62 C67 1.253(2) . ? O63 N62 1.227(2) . ? O64 N62 1.222(2) . ? N61 C69 1.325(2) . ? N61 C70 1.475(2) . ? N61 H61 0.8800 . ? N62 C64 1.468(2) . ? C61 C62 1.389(3) . ? C61 C66 1.395(3) . ? C61 C67 1.508(3) . ? C62 C63 1.384(3) . ? C62 H62 0.9500 . ? C63 C64 1.380(3) . ? C63 H63 0.9500 . ? C64 C65 1.383(3) . ? C65 C66 1.387(3) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? C67 C68 1.409(3) . ? C68 C69 1.386(3) . ? C68 H68 0.9500 . ? C70 C73 1.513(3) . ? C70 C72 1.523(3) . ? C70 C71 1.530(3) . ? C71 H71A 0.9900 . ? C71 H71B 0.9900 . ? C72 H72A 0.9800 . ? C72 H72B 0.9800 . ? C72 H72C 0.9800 . ? C73 H73A 0.9800 . ? C73 H73B 0.9800 . ? C73 H73C 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 C9 O1 C11 106.63(17) . . ? C9 O1 C11A 107.1(3) . . ? C9 N1 C10 112.04(17) . . ? C9 N1 H1 124.0 . . ? C10 N1 H1 124.0 . . ? O4 N2 O3 123.01(18) . . ? O4 N2 C4 118.85(17) . . ? O3 N2 C4 118.14(18) . . ? C6 C1 C2 119.36(18) . . ? C6 C1 C7 122.75(17) . . ? C2 C1 C7 117.88(17) . . ? C3 C2 C1 120.12(18) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 118.89(18) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 122.50(18) . . ? C3 C4 N2 118.30(18) . . ? C5 C4 N2 119.20(17) . . ? C4 C5 C6 118.17(18) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? C5 C6 C1 120.91(18) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? O2 C7 C8 124.30(18) . . ? O2 C7 C1 117.69(18) . . ? C8 C7 C1 117.90(17) . . ? C9 C8 C7 120.08(18) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? N1 C9 O1 111.13(17) . . ? N1 C9 C8 128.50(19) . . ? O1 C9 C8 120.28(18) . . ? N1 C10 C13A 120.2(6) . . ? N1 C10 C12 111.15(18) . . ? C13A C10 C12 68.4(6) . . ? N1 C10 C11 99.33(16) . . ? C13A C10 C11 136.7(6) . . ? C12 C10 C11 115.3(2) . . ? N1 C10 C11A 102.1(5) . . ? C13A C10 C11A 116.3(8) . . ? C12 C10 C11A 137.4(6) . . ? N1 C10 C12A 102.8(5) . . ? C13A C10 C12A 106.8(8) . . ? C11 C10 C12A 78.4(6) . . ? C11A C10 C12A 107.3(8) . . ? N1 C10 C13 108.39(17) . . ? C12 C10 C13 111.7(2) . . ? C11 C10 C13 110.1(2) . . ? C11A C10 C13 80.5(6) . . ? C12A C10 C13 145.5(6) . . ? O1 C11 C10 104.65(19) . . ? O1 C11 H11A 110.8 . . ? C10 C11 H11A 110.8 . . ? O1 C11 H11B 110.8 . . ? C10 C11 H11B 110.8 . . ? H11A C11 H11B 108.9 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? C10 C11A O1 100.9(6) . . ? C10 C11A H11C 111.6 . . ? O1 C11A H11C 111.6 . . ? C10 C11A H11D 111.6 . . ? O1 C11A H11D 111.6 . . ? H11C C11A H11D 109.4 . . ? C10 C12A H12D 109.5 . . ? C10 C12A H12E 109.5 . . ? H12D C12A H12E 109.5 . . ? C10 C12A H12F 109.5 . . ? H12D C12A H12F 109.5 . . ? H12E C12A H12F 109.5 . . ? C10 C13A H13D 109.5 . . ? C10 C13A H13E 109.5 . . ? H13D C13A H13E 109.5 . . ? C10 C13A H13F 109.5 . . ? H13D C13A H13F 109.5 . . ? H13E C13A H13F 109.5 . . ? C29 O21 C31 107.49(15) . . ? C29 N21 C30 111.88(16) . . ? C29 N21 H21 124.1 . . ? C30 N21 H21 124.1 . . ? O23 N22 O24 123.41(18) . . ? O23 N22 C24 118.26(18) . . ? O24 N22 C24 118.33(18) . . ? C26 C21 C22 119.78(17) . . ? C26 C21 C27 122.34(17) . . ? C22 C21 C27 117.81(17) . . ? C23 C22 C21 120.24(18) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C24 C23 C22 118.26(18) . . ? C24 C23 H23 120.9 . . ? C22 C23 H23 120.9 . . ? C25 C24 C23 123.29(18) . . ? C25 C24 N22 118.53(18) . . ? C23 C24 N22 118.15(18) . . ? C24 C25 C26 117.87(18) . . ? C24 C25 H25 121.1 . . ? C26 C25 H25 121.1 . . ? C25 C26 C21 120.52(19) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? O22 C27 C28 124.08(17) . . ? O22 C27 C21 116.98(17) . . ? C28 C27 C21 118.92(17) . . ? C29 C28 C27 119.54(18) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? N21 C29 O21 110.82(16) . . ? N21 C29 C28 127.45(18) . . ? O21 C29 C28 121.69(17) . . ? N21 C30 C32 112.04(16) . . ? N21 C30 C33 109.63(16) . . ? C32 C30 C33 111.54(17) . . ? N21 C30 C31 97.91(14) . . ? C32 C30 C31 113.09(16) . . ? C33 C30 C31 111.90(17) . . ? O21 C31 C30 105.09(15) . . ? O21 C31 H31A 110.7 . . ? C30 C31 H31A 110.7 . . ? O21 C31 H31B 110.7 . . ? C30 C31 H31B 110.7 . . ? H31A C31 H31B 108.8 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C49 O41 C51 107.32(15) . . ? C49 N41 C50 111.76(16) . . ? C49 N41 H41 124.1 . . ? C50 N41 H41 124.1 . . ? O44 N42 O43 123.50(18) . . ? O44 N42 C44 118.71(17) . . ? O43 N42 C44 117.79(17) . . ? C46 C41 C42 119.64(17) . . ? C46 C41 C47 123.13(16) . . ? C42 C41 C47 117.17(16) . . ? C43 C42 C41 120.35(17) . . ? C43 C42 H42 119.8 . . ? C41 C42 H42 119.8 . . ? C44 C43 C42 118.33(17) . . ? C44 C43 H43 120.8 . . ? C42 C43 H43 120.8 . . ? C43 C44 C45 122.99(17) . . ? C43 C44 N42 118.00(17) . . ? C45 C44 N42 119.00(17) . . ? C44 C45 C46 117.85(17) . . ? C44 C45 H45 121.1 . . ? C46 C45 H45 121.1 . . ? C45 C46 C41 120.79(18) . . ? C45 C46 H46 119.6 . . ? C41 C46 H46 119.6 . . ? O42 C47 C48 123.88(17) . . ? O42 C47 C41 116.79(17) . . ? C48 C47 C41 119.32(16) . . ? C49 C48 C47 118.91(17) . . ? C49 C48 H48 120.5 . . ? C47 C48 H48 120.5 . . ? N41 C49 O41 111.09(16) . . ? N41 C49 C48 127.51(18) . . ? O41 C49 C48 121.36(17) . . ? N41 C50 C53 111.32(16) . . ? N41 C50 C51 98.17(14) . . ? C53 C50 C51 113.28(17) . . ? N41 C50 C52 109.72(16) . . ? C53 C50 C52 111.48(17) . . ? C51 C50 C52 112.15(18) . . ? O41 C51 C50 105.02(15) . . ? O41 C51 H51A 110.7 . . ? C50 C51 H51A 110.7 . . ? O41 C51 H51B 110.7 . . ? C50 C51 H51B 110.7 . . ? H51A C51 H51B 108.8 . . ? C50 C52 H52A 109.5 . . ? C50 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C50 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C50 C53 H53A 109.5 . . ? C50 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C50 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C69 O61 C71 107.65(15) . . ? C69 N61 C70 111.67(16) . . ? C69 N61 H61 124.2 . . ? C70 N61 H61 124.2 . . ? O64 N62 O63 123.13(18) . . ? O64 N62 C64 118.90(17) . . ? O63 N62 C64 117.96(17) . . ? C62 C61 C66 119.42(18) . . ? C62 C61 C67 117.26(16) . . ? C66 C61 C67 123.27(17) . . ? C63 C62 C61 120.63(18) . . ? C63 C62 H62 119.7 . . ? C61 C62 H62 119.7 . . ? C64 C63 C62 118.56(18) . . ? C64 C63 H63 120.7 . . ? C62 C63 H63 120.7 . . ? C63 C64 C65 122.50(18) . . ? C63 C64 N62 118.36(17) . . ? C65 C64 N62 119.13(17) . . ? C64 C65 C66 118.19(18) . . ? C64 C65 H65 120.9 . . ? C66 C65 H65 120.9 . . ? C65 C66 C61 120.64(18) . . ? C65 C66 H66 119.7 . . ? C61 C66 H66 119.7 . . ? O62 C67 C68 123.75(17) . . ? O62 C67 C61 116.81(17) . . ? C68 C67 C61 119.43(17) . . ? C69 C68 C67 119.34(18) . . ? C69 C68 H68 120.3 . . ? C67 C68 H68 120.3 . . ? N61 C69 O61 111.17(16) . . ? N61 C69 C68 127.42(18) . . ? O61 C69 C68 121.36(17) . . ? N61 C70 C73 111.45(16) . . ? N61 C70 C72 109.55(16) . . ? C73 C70 C72 111.48(17) . . ? N61 C70 C71 98.42(14) . . ? C73 C70 C71 113.43(17) . . ? C72 C70 C71 111.81(18) . . ? O61 C71 C70 105.14(15) . . ? O61 C71 H71A 110.7 . . ? C70 C71 H71A 110.7 . . ? O61 C71 H71B 110.7 . . ? C70 C71 H71B 110.7 . . ? H71A C71 H71B 108.8 . . ? C70 C72 H72A 109.5 . . ? C70 C72 H72B 109.5 . . ? H72A C72 H72B 109.5 . . ? C70 C72 H72C 109.5 . . ? H72A C72 H72C 109.5 . . ? H72B C72 H72C 109.5 . . ? C70 C73 H73A 109.5 . . ? C70 C73 H73B 109.5 . . ? H73A C73 H73B 109.5 . . ? C70 C73 H73C 109.5 . . ? H73A C73 H73C 109.5 . . ? H73B C73 H73C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.7(3) . . . . ? C7 C1 C2 C3 177.02(18) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C5 1.8(3) . . . . ? C2 C3 C4 N2 -177.46(18) . . . . ? O4 N2 C4 C3 -176.74(18) . . . . ? O3 N2 C4 C3 3.1(3) . . . . ? O4 N2 C4 C5 3.9(3) . . . . ? O3 N2 C4 C5 -176.2(2) . . . . ? C3 C4 C5 C6 -1.1(3) . . . . ? N2 C4 C5 C6 178.15(18) . . . . ? C4 C5 C6 C1 -1.0(3) . . . . ? C2 C1 C6 C5 2.4(3) . . . . ? C7 C1 C6 C5 -176.22(19) . . . . ? C6 C1 C7 O2 141.7(2) . . . . ? C2 C1 C7 O2 -37.0(3) . . . . ? C6 C1 C7 C8 -41.9(3) . . . . ? C2 C1 C7 C8 139.5(2) . . . . ? O2 C7 C8 C9 7.9(3) . . . . ? C1 C7 C8 C9 -168.30(19) . . . . ? C10 N1 C9 O1 0.8(3) . . . . ? C10 N1 C9 C8 177.3(2) . . . . ? C11 O1 C9 N1 15.2(3) . . . . ? C11A O1 C9 N1 -16.9(7) . . . . ? C11 O1 C9 C8 -161.6(2) . . . . ? C11A O1 C9 C8 166.3(6) . . . . ? C7 C8 C9 N1 -7.1(4) . . . . ? C7 C8 C9 O1 169.1(2) . . . . ? C9 N1 C10 C13A 146.1(7) . . . . ? C9 N1 C10 C12 -137.3(2) . . . . ? C9 N1 C10 C11 -15.4(2) . . . . ? C9 N1 C10 C11A 15.6(7) . . . . ? C9 N1 C10 C12A -95.5(6) . . . . ? C9 N1 C10 C13 99.5(2) . . . . ? C9 O1 C11 C10 -24.3(3) . . . . ? C11A O1 C11 C10 71.2(5) . . . . ? N1 C10 C11 O1 23.0(3) . . . . ? C13A C10 C11 O1 -133.5(8) . . . . ? C12 C10 C11 O1 141.8(2) . . . . ? C11A C10 C11 O1 -75.1(11) . . . . ? C12A C10 C11 O1 124.2(6) . . . . ? C13 C10 C11 O1 -90.6(3) . . . . ? N1 C10 C11A O1 -23.1(9) . . . . ? C13A C10 C11A O1 -155.9(8) . . . . ? C12 C10 C11A O1 118.1(7) . . . . ? C11 C10 C11A O1 64.7(9) . . . . ? C12A C10 C11A O1 84.6(10) . . . . ? C13 C10 C11A O1 -130.0(9) . . . . ? C9 O1 C11A C10 25.1(10) . . . . ? C11 O1 C11A C10 -68.8(5) . . . . ? C26 C21 C22 C23 0.3(3) . . . . ? C27 C21 C22 C23 -176.84(18) . . . . ? C21 C22 C23 C24 1.4(3) . . . . ? C22 C23 C24 C25 -1.5(3) . . . . ? C22 C23 C24 N22 176.54(17) . . . . ? O23 N22 C24 C25 -178.31(19) . . . . ? O24 N22 C24 C25 2.3(3) . . . . ? O23 N22 C24 C23 3.6(3) . . . . ? O24 N22 C24 C23 -175.82(19) . . . . ? C23 C24 C25 C26 -0.2(3) . . . . ? N22 C24 C25 C26 -178.20(18) . . . . ? C24 C25 C26 C21 2.0(3) . . . . ? C22 C21 C26 C25 -2.1(3) . . . . ? C27 C21 C26 C25 174.99(19) . . . . ? C26 C21 C27 O22 -146.07(19) . . . . ? C22 C21 C27 O22 31.0(3) . . . . ? C26 C21 C27 C28 35.5(3) . . . . ? C22 C21 C27 C28 -147.43(19) . . . . ? O22 C27 C28 C29 -6.1(3) . . . . ? C21 C27 C28 C29 172.26(18) . . . . ? C30 N21 C29 O21 12.7(2) . . . . ? C30 N21 C29 C28 -165.1(2) . . . . ? C31 O21 C29 N21 5.2(2) . . . . ? C31 O21 C29 C28 -176.78(19) . . . . ? C27 C28 C29 N21 5.6(3) . . . . ? C27 C28 C29 O21 -172.12(18) . . . . ? C29 N21 C30 C32 -142.18(17) . . . . ? C29 N21 C30 C33 93.4(2) . . . . ? C29 N21 C30 C31 -23.3(2) . . . . ? C29 O21 C31 C30 -19.8(2) . . . . ? N21 C30 C31 O21 24.67(19) . . . . ? C32 C30 C31 O21 142.77(17) . . . . ? C33 C30 C31 O21 -90.25(19) . . . . ? C46 C41 C42 C43 -1.1(3) . . . . ? C47 C41 C42 C43 176.21(17) . . . . ? C41 C42 C43 C44 -0.8(3) . . . . ? C42 C43 C44 C45 1.6(3) . . . . ? C42 C43 C44 N42 -177.54(17) . . . . ? O44 N42 C44 C43 -176.13(19) . . . . ? O43 N42 C44 C43 4.7(3) . . . . ? O44 N42 C44 C45 4.7(3) . . . . ? O43 N42 C44 C45 -174.48(18) . . . . ? C43 C44 C45 C46 -0.3(3) . . . . ? N42 C44 C45 C46 178.81(17) . . . . ? C44 C45 C46 C41 -1.7(3) . . . . ? C42 C41 C46 C45 2.5(3) . . . . ? C47 C41 C46 C45 -174.72(19) . . . . ? C46 C41 C47 O42 147.34(19) . . . . ? C42 C41 C47 O42 -29.9(3) . . . . ? C46 C41 C47 C48 -34.0(3) . . . . ? C42 C41 C47 C48 148.79(19) . . . . ? O42 C47 C48 C49 4.6(3) . . . . ? C41 C47 C48 C49 -173.96(18) . . . . ? C50 N41 C49 O41 -12.3(2) . . . . ? C50 N41 C49 C48 165.3(2) . . . . ? C51 O41 C49 N41 -5.3(2) . . . . ? C51 O41 C49 C48 176.87(19) . . . . ? C47 C48 C49 N41 -4.3(3) . . . . ? C47 C48 C49 O41 173.14(18) . . . . ? C49 N41 C50 C53 141.94(18) . . . . ? C49 N41 C50 C51 22.9(2) . . . . ? C49 N41 C50 C52 -94.2(2) . . . . ? C49 O41 C51 C50 19.7(2) . . . . ? N41 C50 C51 O41 -24.37(19) . . . . ? C53 C50 C51 O41 -141.87(17) . . . . ? C52 C50 C51 O41 90.87(19) . . . . ? C66 C61 C62 C63 -2.5(3) . . . . ? C67 C61 C62 C63 175.04(18) . . . . ? C61 C62 C63 C64 0.4(3) . . . . ? C62 C63 C64 C65 1.6(3) . . . . ? C62 C63 C64 N62 -177.02(18) . . . . ? O64 N62 C64 C63 -170.24(18) . . . . ? O63 N62 C64 C63 10.0(3) . . . . ? O64 N62 C64 C65 11.1(3) . . . . ? O63 N62 C64 C65 -168.7(2) . . . . ? C63 C64 C65 C66 -1.4(3) . . . . ? N62 C64 C65 C66 177.22(18) . . . . ? C64 C65 C66 C61 -0.8(3) . . . . ? C62 C61 C66 C65 2.7(3) . . . . ? C67 C61 C66 C65 -174.68(19) . . . . ? C62 C61 C67 O62 -24.9(3) . . . . ? C66 C61 C67 O62 152.57(19) . . . . ? C62 C61 C67 C68 153.81(19) . . . . ? C66 C61 C67 C68 -28.7(3) . . . . ? O62 C67 C68 C69 4.2(3) . . . . ? C61 C67 C68 C69 -174.42(18) . . . . ? C70 N61 C69 O61 -12.0(2) . . . . ? C70 N61 C69 C68 165.3(2) . . . . ? C71 O61 C69 N61 -4.7(2) . . . . ? C71 O61 C69 C68 177.78(19) . . . . ? C67 C68 C69 N61 -4.3(3) . . . . ? C67 C68 C69 O61 172.79(18) . . . . ? C69 N61 C70 C73 141.19(18) . . . . ? C69 N61 C70 C72 -95.0(2) . . . . ? C69 N61 C70 C71 21.8(2) . . . . ? C69 O61 C71 C70 18.4(2) . . . . ? N61 C70 C71 O61 -23.07(19) . . . . ? C73 C70 C71 O61 -140.91(17) . . . . ? C72 C70 C71 O61 91.99(19) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.268 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.045 data_k1050 _database_code_depnum_ccdc_archive 'CCDC 799951' #TrackingRef '- 799951.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H19 N O2' _chemical_formula_sum 'C11 H19 N O2' _chemical_formula_weight 197.27 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 b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 9.7809(3) _cell_length_b 11.4606(4) _cell_length_c 20.8757(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2340.12(13) _cell_formula_units_Z 8 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 7731 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.120 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.076 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.853 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 15839 _diffrn_reflns_av_R_equivalents 0.098 _diffrn_reflns_av_sigmaI/netI 0.068 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.0 _reflns_number_total 2062 _reflns_number_gt 1072 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.1368P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2062 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1395 _refine_ls_R_factor_gt 0.0691 _refine_ls_wR_factor_ref 0.2306 _refine_ls_wR_factor_gt 0.1759 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 O1 O 0.4581(2) 0.26170(19) 0.67443(11) 0.0386(7) Uani 1 1 d . . . O2 O 0.1474(2) 0.4965(2) 0.71971(11) 0.0461(7) Uani 1 1 d . . . N1 N 0.3320(3) 0.4130(2) 0.75942(13) 0.0367(7) Uani 1 1 d . . . H1N H 0.393(3) 0.350(3) 0.7627(16) 0.051(10) Uiso 1 1 d . . . C1 C 0.3586(3) 0.2791(3) 0.63769(15) 0.0321(8) Uani 1 1 d . . . C2 C 0.3553(3) 0.2205(3) 0.57134(15) 0.0354(9) Uani 1 1 d . . . C3 C 0.4751(3) 0.1373(3) 0.56485(16) 0.0483(10) Uani 1 1 d . . . H3A H 0.4664 0.0747 0.5966 0.072 Uiso 1 1 calc R . . H3B H 0.5606 0.1798 0.5721 0.072 Uiso 1 1 calc R . . H3C H 0.4755 0.1036 0.5217 0.072 Uiso 1 1 calc R . . C4 C 0.3641(4) 0.3153(3) 0.51995(16) 0.0482(10) Uani 1 1 d . . . H4A H 0.4476 0.3612 0.5263 0.072 Uiso 1 1 calc R . . H4B H 0.2842 0.3666 0.5231 0.072 Uiso 1 1 calc R . . H4C H 0.3663 0.2789 0.4775 0.072 Uiso 1 1 calc R . . C5 C 0.2216(3) 0.1525(3) 0.56317(16) 0.0474(10) Uani 1 1 d . . . H5A H 0.2140 0.0939 0.5971 0.071 Uiso 1 1 calc R . . H5B H 0.2212 0.1138 0.5213 0.071 Uiso 1 1 calc R . . H5C H 0.1441 0.2065 0.5658 0.071 Uiso 1 1 calc R . . C6 C 0.2488(3) 0.3547(3) 0.65405(15) 0.0394(9) Uani 1 1 d . . . H6A H 0.1746 0.3624 0.6250 0.047 Uiso 1 1 calc R . . C7 C 0.2456(3) 0.4167(3) 0.70989(15) 0.0366(8) Uani 1 1 d . . . C8 C 0.1827(3) 0.5618(3) 0.77696(16) 0.0459(10) Uani 1 1 d . . . H8A H 0.1001 0.5789 0.8027 0.055 Uiso 1 1 calc R . . H8B H 0.2280 0.6363 0.7657 0.055 Uiso 1 1 calc R . . C9 C 0.2806(3) 0.4820(3) 0.81394(16) 0.0405(9) Uani 1 1 d . . . C10 C 0.2069(4) 0.4021(4) 0.86046(18) 0.0621(12) Uani 1 1 d . . . H10A H 0.2702 0.3422 0.8759 0.093 Uiso 1 1 calc R . . H10B H 0.1297 0.3647 0.8387 0.093 Uiso 1 1 calc R . . H10C H 0.1731 0.4479 0.8968 0.093 Uiso 1 1 calc R . . C11 C 0.3951(4) 0.5481(4) 0.84595(19) 0.0615(12) Uani 1 1 d . . . H11A H 0.4600 0.4927 0.8647 0.092 Uiso 1 1 calc R . . H11B H 0.3574 0.5980 0.8798 0.092 Uiso 1 1 calc R . . H11C H 0.4421 0.5965 0.8142 0.092 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0411(13) 0.0374(14) 0.0372(14) -0.0023(11) -0.0073(11) 0.0040(10) O2 0.0500(14) 0.0515(15) 0.0368(14) -0.0067(11) -0.0050(11) 0.0192(12) N1 0.0423(15) 0.0350(17) 0.0327(17) -0.0023(13) -0.0043(13) 0.0089(14) C1 0.0402(18) 0.0266(18) 0.0295(18) 0.0054(14) 0.0005(16) -0.0030(14) C2 0.0426(18) 0.036(2) 0.0279(18) -0.0016(14) -0.0011(15) 0.0025(16) C3 0.056(2) 0.049(2) 0.040(2) -0.0155(18) -0.0052(17) 0.0100(18) C4 0.063(2) 0.049(2) 0.033(2) 0.0002(17) 0.0025(18) -0.0002(19) C5 0.053(2) 0.047(2) 0.042(2) -0.0051(17) -0.0077(17) -0.0068(18) C6 0.0376(17) 0.041(2) 0.039(2) -0.0060(16) -0.0027(16) 0.0079(16) C7 0.0367(17) 0.0352(19) 0.038(2) -0.0002(16) 0.0046(16) 0.0062(16) C8 0.055(2) 0.045(2) 0.037(2) -0.0048(17) -0.0036(17) 0.0138(18) C9 0.0479(19) 0.041(2) 0.0321(19) -0.0043(16) 0.0036(16) 0.0077(17) C10 0.076(3) 0.064(3) 0.045(2) 0.009(2) 0.010(2) 0.027(2) C11 0.069(2) 0.060(3) 0.056(3) -0.019(2) -0.011(2) 0.013(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 1.255(4) . ? O2 C7 1.343(4) . ? O2 C8 1.452(4) . ? N1 C7 1.336(4) . ? N1 C9 1.474(4) . ? C1 C6 1.422(4) . ? C1 C2 1.540(4) . ? C2 C3 1.517(4) . ? C2 C4 1.529(5) . ? C2 C5 1.532(4) . ? C6 C7 1.365(4) . ? C8 C9 1.533(4) . ? C9 C11 1.508(5) . ? C9 C10 1.517(5) . ? 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 O2 C8 107.8(2) . . ? C7 N1 C9 111.4(3) . . ? O1 C1 C6 122.4(3) . . ? O1 C1 C2 119.8(3) . . ? C6 C1 C2 117.8(3) . . ? C3 C2 C4 109.9(3) . . ? C3 C2 C5 109.2(3) . . ? C4 C2 C5 109.3(3) . . ? C3 C2 C1 109.8(2) . . ? C4 C2 C1 108.7(3) . . ? C5 C2 C1 109.9(2) . . ? C7 C6 C1 122.6(3) . . ? N1 C7 O2 110.8(3) . . ? N1 C7 C6 129.1(3) . . ? O2 C7 C6 120.1(3) . . ? O2 C8 C9 104.8(3) . . ? N1 C9 C11 111.0(3) . . ? N1 C9 C10 109.4(3) . . ? C11 C9 C10 111.9(3) . . ? N1 C9 C8 98.3(3) . . ? C11 C9 C8 112.8(3) . . ? C10 C9 C8 112.7(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.94(4) 2.20(4) 2.771(4) 118(3) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.361 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.065 data_k11192 _database_code_depnum_ccdc_archive 'CCDC 860691' #TrackingRef '- 860691.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H16 N O2, H O4 S' _chemical_formula_sum 'C13 H17 N O6 S' _chemical_formula_weight 315.34 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' S S 0.1246 0.1234 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0340(4) _cell_length_b 9.1042(5) _cell_length_c 11.2816(7) _cell_angle_alpha 70.084(3) _cell_angle_beta 70.430(3) _cell_angle_gamma 80.387(4) _cell_volume 729.70(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 6647 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.249 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.837 _exptl_absorpt_correction_T_max 0.924 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6647 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0686 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3295 _reflns_number_gt 2090 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0765P)^2^+0.4450P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3295 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1060 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1670 _refine_ls_wR_factor_gt 0.1347 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 -0.1017(3) 0.2681(2) 0.9929(2) 0.0414(6) Uani 1 1 d . . . O2 O -0.1391(3) 0.0976(2) 0.8152(2) 0.0323(5) Uani 1 1 d . . . N1 N 0.0857(3) 0.2333(3) 0.6751(2) 0.0281(6) Uani 1 1 d . . . C1 C -0.2508(4) 0.5196(3) 0.9638(3) 0.0282(6) Uani 1 1 d . . . C2 C -0.3176(4) 0.6498(3) 0.8801(3) 0.0332(7) Uani 1 1 d . . . H2A H -0.3124 0.6496 0.7948 0.040 Uiso 1 1 calc R . . C3 C -0.3914(4) 0.7794(4) 0.9218(3) 0.0375(7) Uani 1 1 d . . . H3A H -0.4343 0.8689 0.8640 0.045 Uiso 1 1 calc R . . C4 C -0.4031(4) 0.7791(4) 1.0465(3) 0.0368(7) Uani 1 1 d . . . H4A H -0.4550 0.8678 1.0749 0.044 Uiso 1 1 calc R . . C5 C -0.3388(4) 0.6491(4) 1.1307(3) 0.0398(8) Uani 1 1 d . . . H5A H -0.3476 0.6485 1.2170 0.048 Uiso 1 1 calc R . . C6 C -0.2623(4) 0.5208(3) 1.0894(3) 0.0329(7) Uani 1 1 d . . . H6A H -0.2171 0.4326 1.1469 0.040 Uiso 1 1 calc R . . C7 C -0.1689(4) 0.3783(3) 0.9228(3) 0.0296(7) Uani 1 1 d . . . C8 C -0.1689(4) 0.3758(3) 0.7890(3) 0.0310(7) Uani 1 1 d . . . H8A H -0.2924 0.3785 0.7886 0.037 Uiso 1 1 calc R . . H8B H -0.1140 0.4701 0.7198 0.037 Uiso 1 1 calc R . . C9 C -0.0704(4) 0.2342(3) 0.7583(3) 0.0299(6) Uani 1 1 d . . . C10 C -0.0196(4) -0.0122(3) 0.7492(3) 0.0338(7) Uani 1 1 d . . . H10A H -0.0728 -0.0376 0.6917 0.041 Uiso 1 1 calc R . . H10B H 0.0050 -0.1104 0.8153 0.041 Uiso 1 1 calc R . . C11 C 0.1513(4) 0.0738(3) 0.6667(3) 0.0284(6) Uani 1 1 d . . . C12 C 0.2130(4) 0.0775(4) 0.5231(3) 0.0383(7) Uani 1 1 d . . . H12A H 0.3194 0.1370 0.4760 0.057 Uiso 1 1 calc R . . H12B H 0.1194 0.1276 0.4823 0.057 Uiso 1 1 calc R . . H12C H 0.2402 -0.0297 0.5182 0.057 Uiso 1 1 calc R . . C13 C 0.2985(4) 0.0138(4) 0.7319(3) 0.0391(8) Uani 1 1 d . . . H13A H 0.3979 0.0817 0.6841 0.059 Uiso 1 1 calc R . . H13B H 0.3384 -0.0932 0.7294 0.059 Uiso 1 1 calc R . . H13C H 0.2537 0.0144 0.8239 0.059 Uiso 1 1 calc R . . O3 O 0.0990(3) 0.6661(3) 0.6208(2) 0.0446(6) Uani 1 1 d . . . O4 O 0.2919(3) 0.4787(2) 0.5204(2) 0.0362(5) Uani 1 1 d . . . O5 O 0.2982(3) 0.7522(2) 0.3977(2) 0.0412(6) Uani 1 1 d . . . O6 O 0.4074(3) 0.6557(3) 0.5881(2) 0.0371(5) Uani 1 1 d . . . S1 S 0.26458(9) 0.64061(8) 0.52706(7) 0.0314(2) Uani 1 1 d . . . H1N H 0.144(5) 0.319(5) 0.629(4) 0.065(13) Uiso 1 1 d . . . H1O H 0.507(7) 0.604(6) 0.553(5) 0.103(18) 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 0.0529(13) 0.0342(12) 0.0375(13) -0.0106(10) -0.0194(11) 0.0083(10) O2 0.0339(11) 0.0268(11) 0.0306(11) -0.0042(9) -0.0048(9) -0.0071(8) N1 0.0302(12) 0.0231(12) 0.0292(13) -0.0074(10) -0.0070(11) -0.0025(10) C1 0.0278(14) 0.0270(15) 0.0283(15) -0.0074(12) -0.0075(12) -0.0024(11) C2 0.0380(16) 0.0330(16) 0.0288(16) -0.0080(13) -0.0128(13) 0.0001(13) C3 0.0403(17) 0.0324(16) 0.0421(19) -0.0115(14) -0.0180(15) 0.0043(13) C4 0.0375(16) 0.0311(16) 0.045(2) -0.0174(14) -0.0109(14) -0.0008(13) C5 0.0453(18) 0.0430(19) 0.0345(18) -0.0184(15) -0.0113(14) 0.0011(15) C6 0.0391(16) 0.0302(15) 0.0313(16) -0.0096(13) -0.0138(13) 0.0000(13) C7 0.0302(15) 0.0272(15) 0.0279(15) -0.0042(12) -0.0078(12) -0.0035(12) C8 0.0351(15) 0.0268(15) 0.0276(16) -0.0062(12) -0.0071(12) -0.0018(12) C9 0.0351(15) 0.0279(15) 0.0247(15) -0.0039(12) -0.0095(12) -0.0049(12) C10 0.0381(16) 0.0247(15) 0.0423(18) -0.0109(13) -0.0165(14) -0.0010(12) C11 0.0352(15) 0.0185(13) 0.0345(16) -0.0089(12) -0.0132(13) -0.0015(11) C12 0.0481(18) 0.0297(16) 0.0375(18) -0.0127(14) -0.0103(15) -0.0033(14) C13 0.0361(16) 0.0335(17) 0.048(2) -0.0071(15) -0.0194(15) -0.0019(13) O3 0.0328(12) 0.0451(13) 0.0486(14) -0.0182(11) -0.0010(10) 0.0016(10) O4 0.0347(11) 0.0249(11) 0.0477(13) -0.0113(10) -0.0102(10) -0.0027(8) O5 0.0560(14) 0.0292(11) 0.0364(13) -0.0028(9) -0.0186(11) -0.0031(10) O6 0.0392(12) 0.0408(13) 0.0372(13) -0.0162(10) -0.0152(10) -0.0007(10) S1 0.0330(4) 0.0261(4) 0.0338(4) -0.0071(3) -0.0109(3) -0.0010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.219(3) . ? O2 C9 1.308(3) . ? O2 C10 1.477(3) . ? N1 C9 1.291(4) . ? N1 C11 1.483(3) . ? N1 H1N 0.88(4) . ? C1 C6 1.392(4) . ? C1 C2 1.396(4) . ? C1 C7 1.491(4) . ? C2 C3 1.387(4) . ? C2 H2A 0.9500 . ? C3 C4 1.378(5) . ? C3 H3A 0.9500 . ? C4 C5 1.389(4) . ? C4 H4A 0.9500 . ? C5 C6 1.378(4) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.518(4) . ? C8 C9 1.479(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C10 C11 1.540(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.518(4) . ? C11 C13 1.527(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O3 S1 1.436(2) . ? O4 S1 1.478(2) . ? O5 S1 1.432(2) . ? O6 S1 1.567(2) . ? O6 H1O 0.90(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O2 C10 107.1(2) . . ? C9 N1 C11 112.0(2) . . ? C9 N1 H1N 123(3) . . ? C11 N1 H1N 125(3) . . ? C6 C1 C2 119.4(3) . . ? C6 C1 C7 119.0(2) . . ? C2 C1 C7 121.7(3) . . ? C3 C2 C1 119.8(3) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C6 C5 C4 120.1(3) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C5 C6 C1 120.4(3) . . ? C5 C6 H6A 119.8 . . ? C1 C6 H6A 119.8 . . ? O1 C7 C1 121.7(3) . . ? O1 C7 C8 120.4(3) . . ? C1 C7 C8 117.9(2) . . ? C9 C8 C7 111.3(2) . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? N1 C9 O2 114.7(3) . . ? N1 C9 C8 124.3(3) . . ? O2 C9 C8 121.0(3) . . ? O2 C10 C11 105.3(2) . . ? O2 C10 H10A 110.7 . . ? C11 C10 H10A 110.7 . . ? O2 C10 H10B 110.7 . . ? C11 C10 H10B 110.7 . . ? H10A C10 H10B 108.8 . . ? N1 C11 C12 109.4(2) . . ? N1 C11 C13 109.6(2) . . ? C12 C11 C13 112.1(3) . . ? N1 C11 C10 99.1(2) . . ? C12 C11 C10 113.9(3) . . ? C13 C11 C10 112.0(2) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? S1 O6 H1O 107(4) . . ? O5 S1 O3 115.47(13) . . ? O5 S1 O4 111.23(13) . . ? O3 S1 O4 112.22(13) . . ? O5 S1 O6 107.70(13) . . ? O3 S1 O6 104.14(14) . . ? O4 S1 O6 105.20(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O4 0.88(4) 1.85(4) 2.725(3) 171(4) . O6 H1O O4 0.90(5) 1.73(5) 2.624(3) 174(5) 2_666 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.318 _refine_diff_density_min -0.618 _refine_diff_density_rms 0.079 data_k1064 _database_code_depnum_ccdc_archive 'CCDC 915339' #TrackingRef 'web_deposit_cif_file_0_RobertA.Gossage_1355257656.k1064.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H15 N O2' _chemical_formula_sum 'C18 H15 N O2' _chemical_formula_weight 277.31 _chemical_absolute_configuration unk 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 'C 2' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 27.070(4) _cell_length_b 5.0325(4) _cell_length_c 10.3600(14) _cell_angle_alpha 90.00 _cell_angle_beta 103.134(4) _cell_angle_gamma 90.00 _cell_volume 1374.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 3875 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 25.1 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.088 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.870 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD' _diffrn_measurement_method '\f scnas and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 3875 _diffrn_reflns_av_R_equivalents 0.0793 _diffrn_reflns_av_sigmaI/netI 0.0751 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 25.08 _reflns_number_total 1357 _reflns_number_gt 947 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0624P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0065(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ #_refine_ls_abs_structure_details # 'Flack H D (1983), Acta Cryst. A39, 876-881' #_refine_ls_abs_structure_Flack 0(3) _refine_ls_number_reflns 1357 _refine_ls_number_parameters 195 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0837 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.44729(10) 0.6403(6) 0.0602(3) 0.0517(9) Uani 1 1 d . . . O2 O 0.49873(10) 0.0804(6) 0.3512(3) 0.0482(8) Uani 1 1 d . . . N1 N 0.51236(13) 0.2637(8) 0.1696(4) 0.0448(9) Uani 1 1 d . . . H1N H 0.5084(17) 0.387(11) 0.113(4) 0.056(15) Uiso 1 1 d . . . C1 C 0.42388(15) 0.6001(9) 0.1508(4) 0.0419(10) Uani 1 1 d . . . C2 C 0.37490(14) 0.7481(8) 0.1434(4) 0.0371(10) Uani 1 1 d . . . C3 C 0.36287(16) 0.9562(8) 0.0528(4) 0.0462(11) Uani 1 1 d . . . H3A H 0.3859 1.0037 -0.0002 0.055 Uiso 1 1 calc R . . C4 C 0.31797(16) 1.0936(9) 0.0396(4) 0.0470(11) Uani 1 1 d . . . H4A H 0.3103 1.2347 -0.0227 0.056 Uiso 1 1 calc R . . C5 C 0.28413(16) 1.0287(8) 0.1155(4) 0.0446(11) Uani 1 1 d . . . H5A H 0.2532 1.1236 0.1057 0.054 Uiso 1 1 calc R . . C6 C 0.29585(16) 0.8215(8) 0.2071(4) 0.0475(12) Uani 1 1 d . . . H6A H 0.2728 0.7749 0.2602 0.057 Uiso 1 1 calc R . . C7 C 0.34093(14) 0.6845(8) 0.2205(4) 0.0412(11) Uani 1 1 d . . . H7A H 0.3488 0.5446 0.2834 0.049 Uiso 1 1 calc R . . C8 C 0.44068(15) 0.4188(9) 0.2545(4) 0.0418(10) Uani 1 1 d . . . H8A H 0.4232 0.4035 0.3239 0.050 Uiso 1 1 calc R . . C9 C 0.48274(16) 0.2626(8) 0.2552(4) 0.0398(10) Uani 1 1 d . . . C10 C 0.54061(16) -0.0711(9) 0.3218(4) 0.0465(11) Uani 1 1 d . . . H10A H 0.5298 -0.2554 0.2922 0.056 Uiso 1 1 calc R . . C11 C 0.58553(15) -0.0742(9) 0.4403(4) 0.0459(11) Uani 1 1 d . . . H11A H 0.5748 -0.0285 0.5228 0.055 Uiso 1 1 calc R . . H11B H 0.6020 -0.2511 0.4510 0.055 Uiso 1 1 calc R . . C12 C 0.62092(16) 0.1333(8) 0.4081(4) 0.0415(11) Uani 1 1 d . . . C13 C 0.66485(15) 0.2353(9) 0.4873(4) 0.0459(11) Uani 1 1 d . . . H13A H 0.6766 0.1712 0.5752 0.055 Uiso 1 1 calc R . . C14 C 0.69199(16) 0.4330(9) 0.4382(5) 0.0515(12) Uani 1 1 d . . . H14A H 0.7222 0.5033 0.4928 0.062 Uiso 1 1 calc R . . C15 C 0.67505(17) 0.5258(9) 0.3109(4) 0.0495(11) Uani 1 1 d . . . H15A H 0.6935 0.6614 0.2785 0.059 Uiso 1 1 calc R . . C16 C 0.63110(16) 0.4226(9) 0.2288(4) 0.0454(11) Uani 1 1 d . . . H16A H 0.6196 0.4856 0.1406 0.054 Uiso 1 1 calc R . . C17 C 0.60422(14) 0.2241(9) 0.2788(4) 0.0392(10) Uani 1 1 d . . . C18 C 0.55609(15) 0.0898(8) 0.2094(4) 0.0435(11) Uani 1 1 d . . . H18A H 0.5611 -0.0266 0.1352 0.052 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 0.0448(17) 0.067(2) 0.0462(18) 0.0139(15) 0.0163(15) 0.0066(15) O2 0.0487(18) 0.0444(18) 0.0576(18) 0.0125(14) 0.0252(15) 0.0094(15) N1 0.048(2) 0.050(2) 0.038(2) 0.003(2) 0.0133(19) 0.0038(19) C1 0.041(2) 0.046(3) 0.042(2) -0.001(2) 0.015(2) -0.002(2) C2 0.039(2) 0.035(2) 0.038(2) -0.0027(19) 0.0099(19) -0.0062(19) C3 0.044(3) 0.045(3) 0.051(3) 0.006(2) 0.013(2) -0.002(2) C4 0.051(3) 0.038(2) 0.051(3) 0.007(2) 0.012(2) -0.001(2) C5 0.038(2) 0.041(3) 0.056(3) -0.005(2) 0.011(2) 0.001(2) C6 0.044(3) 0.052(3) 0.050(3) -0.003(2) 0.018(2) -0.005(2) C7 0.041(2) 0.043(3) 0.040(2) 0.0029(19) 0.010(2) 0.004(2) C8 0.043(3) 0.042(2) 0.044(3) 0.003(2) 0.018(2) 0.001(2) C9 0.045(2) 0.037(2) 0.038(2) -0.0004(19) 0.011(2) -0.004(2) C10 0.044(3) 0.034(2) 0.065(3) -0.003(2) 0.021(2) 0.003(2) C11 0.050(3) 0.036(2) 0.056(3) 0.003(2) 0.021(2) 0.007(2) C12 0.046(3) 0.032(2) 0.050(3) -0.0031(19) 0.019(2) 0.0047(19) C13 0.047(3) 0.044(3) 0.045(3) -0.002(2) 0.008(2) 0.009(2) C14 0.043(3) 0.045(3) 0.068(3) -0.012(3) 0.016(2) 0.002(2) C15 0.052(3) 0.039(2) 0.064(3) -0.004(2) 0.026(3) -0.001(2) C16 0.055(3) 0.042(2) 0.044(2) 0.001(2) 0.022(2) 0.005(2) C17 0.041(2) 0.037(2) 0.044(2) -0.004(2) 0.018(2) 0.0086(19) C18 0.042(2) 0.042(2) 0.048(3) -0.010(2) 0.014(2) 0.002(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 1.262(5) . ? O2 C9 1.349(5) . ? O2 C10 1.454(5) . ? N1 C9 1.325(5) . ? N1 C18 1.454(6) . ? C1 C8 1.404(6) . ? C1 C2 1.508(6) . ? C2 C7 1.385(5) . ? C2 C3 1.394(6) . ? C3 C4 1.378(6) . ? C4 C5 1.375(5) . ? C5 C6 1.398(6) . ? C6 C7 1.381(5) . ? C8 C9 1.382(6) . ? C10 C11 1.519(6) . ? C10 C18 1.552(6) . ? C11 C12 1.505(6) . ? C12 C13 1.381(6) . ? C12 C17 1.389(5) . ? C13 C14 1.400(6) . ? C14 C15 1.376(6) . ? C15 C16 1.396(6) . ? C16 C17 1.402(6) . ? C17 C18 1.499(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O2 C10 109.7(3) . . ? C9 N1 C18 112.7(4) . . ? O1 C1 C8 122.9(4) . . ? O1 C1 C2 117.9(4) . . ? C8 C1 C2 119.2(4) . . ? C7 C2 C3 118.5(4) . . ? C7 C2 C1 123.2(4) . . ? C3 C2 C1 118.3(3) . . ? C4 C3 C2 120.7(4) . . ? C5 C4 C3 120.7(4) . . ? C4 C5 C6 119.2(4) . . ? C7 C6 C5 120.0(4) . . ? C6 C7 C2 120.9(4) . . ? C9 C8 C1 119.8(4) . . ? N1 C9 O2 110.8(4) . . ? N1 C9 C8 128.1(4) . . ? O2 C9 C8 121.1(4) . . ? O2 C10 C11 110.8(3) . . ? O2 C10 C18 103.9(3) . . ? C11 C10 C18 108.0(3) . . ? C12 C11 C10 104.3(3) . . ? C13 C12 C17 119.9(4) . . ? C13 C12 C11 129.1(4) . . ? C17 C12 C11 111.0(4) . . ? C12 C13 C14 120.0(4) . . ? C15 C14 C13 120.1(4) . . ? C14 C15 C16 120.7(4) . . ? C15 C16 C17 118.8(4) . . ? C12 C17 C16 120.5(4) . . ? C12 C17 C18 111.8(4) . . ? C16 C17 C18 127.7(4) . . ? N1 C18 C17 115.3(3) . . ? N1 C18 C10 100.7(3) . . ? C17 C18 C10 103.2(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.84(5) 2.06(5) 2.659(5) 127(4) . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.172 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.046 data_k09122 _database_code_depnum_ccdc_archive 'CCDC 915340' #TrackingRef 'web_deposit_cif_file_1_RobertA.Gossage_1355257656.k09122.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H28 Cu N2 O4' _chemical_formula_sum 'C26 H28 Cu N2 O4' _chemical_formula_weight 496.04 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' Cu Cu 0.3201 1.2651 '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' _symmetry_space_group_name_Hall '-P 2ybc' 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 12.8657(4) _cell_length_b 13.4020(5) _cell_length_c 14.1823(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.6720(19) _cell_angle_gamma 90.00 _cell_volume 2403.10(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 16014 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1036 _exptl_absorpt_coefficient_mu 0.943 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.834 _exptl_absorpt_correction_T_max 0.934 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16014 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0626 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 27.54 _reflns_number_total 5459 _reflns_number_gt 3872 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0406P)^2^+1.1873P] 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 5459 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Cu1 Cu 0.16621(2) 0.12598(2) 0.736737(19) 0.01991(10) Uani 1 1 d . . . O1 O 0.32541(14) -0.07665(13) 0.92725(12) 0.0265(4) Uani 1 1 d . . . O2 O 0.01888(14) 0.21299(15) 0.46787(12) 0.0318(5) Uani 1 1 d . . . O3 O 0.29991(13) 0.19366(13) 0.77131(11) 0.0248(4) Uani 1 1 d . . . O4 O 0.02107(13) 0.11860(12) 0.75118(11) 0.0217(4) Uani 1 1 d . . . N1 N 0.21086(15) 0.01580(15) 0.82435(13) 0.0201(4) Uani 1 1 d . . . N2 N 0.12898(16) 0.17941(16) 0.60698(14) 0.0225(5) Uani 1 1 d . . . C1 C 0.38002(19) 0.16848(19) 0.83685(17) 0.0212(5) Uani 1 1 d . . . C2 C 0.46968(19) 0.24056(19) 0.85149(18) 0.0229(6) Uani 1 1 d . . . C3 C 0.4905(2) 0.2969(2) 0.7745(2) 0.0307(6) Uani 1 1 d . . . H3A H 0.4480 0.2881 0.7127 0.037 Uiso 1 1 calc R . . C4 C 0.5728(2) 0.3658(2) 0.7872(2) 0.0392(7) Uani 1 1 d . . . H4A H 0.5868 0.4034 0.7342 0.047 Uiso 1 1 calc R . . C5 C 0.6341(2) 0.3796(2) 0.8768(3) 0.0435(8) Uani 1 1 d . . . H5A H 0.6903 0.4266 0.8856 0.052 Uiso 1 1 calc R . . C6 C 0.6137(2) 0.3250(2) 0.9534(2) 0.0381(7) Uani 1 1 d . . . H6A H 0.6552 0.3355 1.0153 0.046 Uiso 1 1 calc R . . C7 C 0.5331(2) 0.2549(2) 0.94126(19) 0.0286(6) Uani 1 1 d . . . H7A H 0.5211 0.2164 0.9945 0.034 Uiso 1 1 calc R . . C8 C 0.38690(19) 0.08176(19) 0.88954(17) 0.0218(5) Uani 1 1 d . . . H8A H 0.4492 0.0695 0.9356 0.026 Uiso 1 1 calc R . . C9 C 0.30458(19) 0.01002(18) 0.87776(16) 0.0209(5) Uani 1 1 d . . . C10 C 0.2390(2) -0.14403(19) 0.88894(19) 0.0287(6) Uani 1 1 d . . . H10A H 0.2172 -0.1836 0.9409 0.034 Uiso 1 1 calc R . . H10B H 0.2600 -0.1902 0.8413 0.034 Uiso 1 1 calc R . . C11 C 0.1497(2) -0.07513(18) 0.84171(17) 0.0234(6) Uani 1 1 d . . . C12 C 0.0761(2) -0.0500(2) 0.91185(19) 0.0310(6) Uani 1 1 d . . . H12A H 0.0233 -0.0010 0.8824 0.046 Uiso 1 1 calc R . . H12B H 0.1177 -0.0220 0.9708 0.046 Uiso 1 1 calc R . . H12C H 0.0403 -0.1108 0.9272 0.046 Uiso 1 1 calc R . . C13 C 0.0889(2) -0.1180(2) 0.74839(19) 0.0315(6) Uani 1 1 d . . . H13A H 0.1380 -0.1323 0.7050 0.047 Uiso 1 1 calc R . . H13B H 0.0359 -0.0696 0.7183 0.047 Uiso 1 1 calc R . . H13C H 0.0535 -0.1797 0.7618 0.047 Uiso 1 1 calc R . . C14 C -0.06111(19) 0.11818(17) 0.68307(17) 0.0200(5) Uani 1 1 d . . . C15 C -0.16305(19) 0.09147(18) 0.71330(17) 0.0224(6) Uani 1 1 d . . . C16 C -0.1818(2) 0.12180(19) 0.80227(19) 0.0263(6) Uani 1 1 d . . . H16A H -0.1287 0.1569 0.8450 0.032 Uiso 1 1 calc R . . C17 C -0.2782(2) 0.1009(2) 0.8291(2) 0.0318(7) Uani 1 1 d . . . H17A H -0.2913 0.1233 0.8893 0.038 Uiso 1 1 calc R . . C18 C -0.3551(2) 0.0477(2) 0.7681(2) 0.0353(7) Uani 1 1 d . . . H18A H -0.4209 0.0336 0.7865 0.042 Uiso 1 1 calc R . . C19 C -0.3359(2) 0.0151(2) 0.6810(2) 0.0361(7) Uani 1 1 d . . . H19A H -0.3880 -0.0226 0.6396 0.043 Uiso 1 1 calc R . . C20 C -0.2407(2) 0.0373(2) 0.65355(18) 0.0283(6) Uani 1 1 d . . . H20A H -0.2283 0.0152 0.5930 0.034 Uiso 1 1 calc R . . C21 C -0.0601(2) 0.14215(19) 0.58903(17) 0.0237(6) Uani 1 1 d . . . H21A H -0.1235 0.1356 0.5430 0.028 Uiso 1 1 calc R . . C22 C 0.0324(2) 0.17626(19) 0.55875(17) 0.0236(6) Uani 1 1 d . . . C23 C 0.1237(2) 0.2346(2) 0.44905(19) 0.0362(7) Uani 1 1 d . . . H23A H 0.1253 0.3012 0.4192 0.043 Uiso 1 1 calc R . . H23B H 0.1451 0.1839 0.4056 0.043 Uiso 1 1 calc R . . C24 C 0.1974(2) 0.2317(2) 0.54771(17) 0.0264(6) Uani 1 1 d . . . C25 C 0.2972(2) 0.1716(2) 0.54481(19) 0.0332(7) Uani 1 1 d . . . H25A H 0.3421 0.1714 0.6086 0.050 Uiso 1 1 calc R . . H25B H 0.3358 0.2019 0.4986 0.050 Uiso 1 1 calc R . . H25C H 0.2778 0.1030 0.5253 0.050 Uiso 1 1 calc R . . C26 C 0.2228(2) 0.3363(2) 0.5883(2) 0.0330(7) Uani 1 1 d . . . H26A H 0.2601 0.3313 0.6550 0.049 Uiso 1 1 calc R . . H26B H 0.1569 0.3737 0.5860 0.049 Uiso 1 1 calc R . . H26C H 0.2677 0.3710 0.5500 0.049 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 Cu1 0.01972(17) 0.02011(17) 0.01956(16) 0.00261(13) 0.00272(12) -0.00122(13) O1 0.0275(10) 0.0183(10) 0.0316(10) 0.0065(8) 0.0000(8) -0.0015(8) O2 0.0309(11) 0.0429(12) 0.0200(9) 0.0091(8) 0.0006(8) 0.0013(9) O3 0.0217(9) 0.0262(10) 0.0252(9) 0.0061(8) 0.0009(7) -0.0038(8) O4 0.0208(9) 0.0245(10) 0.0193(8) 0.0011(7) 0.0025(7) 0.0004(8) N1 0.0207(11) 0.0185(11) 0.0215(10) 0.0005(9) 0.0045(8) -0.0028(9) N2 0.0250(12) 0.0231(12) 0.0201(10) 0.0026(9) 0.0058(9) -0.0020(9) C1 0.0195(13) 0.0236(14) 0.0215(12) -0.0031(11) 0.0062(10) 0.0011(11) C2 0.0177(13) 0.0189(13) 0.0331(14) -0.0011(11) 0.0072(11) 0.0030(10) C3 0.0229(14) 0.0297(16) 0.0415(16) 0.0018(13) 0.0113(12) 0.0001(12) C4 0.0307(16) 0.0305(17) 0.061(2) 0.0115(15) 0.0194(15) -0.0018(13) C5 0.0238(16) 0.0287(17) 0.078(2) -0.0023(16) 0.0091(16) -0.0073(13) C6 0.0251(15) 0.0298(17) 0.0547(19) -0.0083(15) -0.0049(13) -0.0008(13) C7 0.0223(14) 0.0254(15) 0.0368(15) -0.0018(12) 0.0023(11) 0.0028(12) C8 0.0186(13) 0.0224(14) 0.0236(13) -0.0006(11) 0.0015(10) -0.0004(11) C9 0.0264(14) 0.0176(13) 0.0201(12) 0.0017(10) 0.0086(10) 0.0044(11) C10 0.0298(15) 0.0207(15) 0.0341(14) 0.0040(11) 0.0022(12) -0.0036(11) C11 0.0270(14) 0.0155(13) 0.0271(13) 0.0026(11) 0.0033(11) -0.0023(11) C12 0.0290(15) 0.0283(15) 0.0370(15) 0.0066(12) 0.0102(12) -0.0048(12) C13 0.0351(16) 0.0210(14) 0.0347(15) -0.0017(12) -0.0034(12) -0.0061(12) C14 0.0238(13) 0.0134(12) 0.0229(12) -0.0022(10) 0.0043(10) 0.0029(10) C15 0.0204(13) 0.0166(13) 0.0294(14) 0.0061(11) 0.0022(11) 0.0038(10) C16 0.0248(14) 0.0212(14) 0.0319(14) -0.0008(12) 0.0025(11) 0.0011(11) C17 0.0322(16) 0.0333(16) 0.0330(15) 0.0003(13) 0.0142(12) 0.0032(13) C18 0.0226(15) 0.0411(18) 0.0436(16) 0.0063(14) 0.0102(13) -0.0032(13) C19 0.0292(16) 0.0376(18) 0.0393(17) -0.0004(14) 0.0008(13) -0.0095(13) C20 0.0281(15) 0.0294(15) 0.0267(13) -0.0023(12) 0.0027(11) -0.0039(12) C21 0.0212(13) 0.0263(15) 0.0218(12) -0.0011(11) -0.0004(10) -0.0007(11) C22 0.0311(15) 0.0205(14) 0.0189(12) 0.0010(11) 0.0040(11) 0.0027(11) C23 0.0338(16) 0.0489(19) 0.0266(14) 0.0102(13) 0.0070(12) -0.0011(14) C24 0.0291(15) 0.0296(15) 0.0219(12) 0.0060(11) 0.0087(11) -0.0009(12) C25 0.0321(16) 0.0406(17) 0.0292(14) 0.0001(13) 0.0117(12) 0.0006(13) C26 0.0322(16) 0.0279(15) 0.0396(16) 0.0105(13) 0.0090(13) -0.0002(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.9184(16) . ? Cu1 O3 1.9261(17) . ? Cu1 N1 1.947(2) . ? Cu1 N2 1.9499(19) . ? O1 C9 1.358(3) . ? O1 C10 1.457(3) . ? O2 C22 1.360(3) . ? O2 C23 1.451(3) . ? O3 C1 1.298(3) . ? O4 C14 1.293(3) . ? N1 C9 1.302(3) . ? N1 C11 1.496(3) . ? N2 C22 1.304(3) . ? N2 C24 1.499(3) . ? C1 C8 1.376(4) . ? C1 C2 1.489(3) . ? C2 C7 1.392(3) . ? C2 C3 1.394(4) . ? C3 C4 1.392(4) . ? C4 C5 1.378(5) . ? C5 C6 1.375(4) . ? C6 C7 1.386(4) . ? C8 C9 1.417(3) . ? C10 C11 1.529(4) . ? C11 C13 1.520(3) . ? C11 C12 1.532(3) . ? C14 C21 1.374(3) . ? C14 C15 1.497(3) . ? C15 C16 1.389(4) . ? C15 C20 1.389(3) . ? C16 C17 1.390(4) . ? C17 C18 1.385(4) . ? C18 C19 1.376(4) . ? C19 C20 1.384(4) . ? C21 C22 1.414(3) . ? C23 C24 1.539(4) . ? C24 C25 1.522(4) . ? C24 C26 1.528(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 O4 Cu1 O3 146.95(7) . . ? O4 Cu1 N1 94.06(8) . . ? O3 Cu1 N1 92.90(8) . . ? O4 Cu1 N2 92.63(8) . . ? O3 Cu1 N2 96.83(8) . . ? N1 Cu1 N2 150.79(9) . . ? C9 O1 C10 105.88(18) . . ? C22 O2 C23 106.65(19) . . ? C1 O3 Cu1 127.81(16) . . ? C14 O4 Cu1 126.71(15) . . ? C9 N1 C11 108.3(2) . . ? C9 N1 Cu1 123.26(16) . . ? C11 N1 Cu1 128.39(15) . . ? C22 N2 C24 108.8(2) . . ? C22 N2 Cu1 121.80(16) . . ? C24 N2 Cu1 129.33(16) . . ? O3 C1 C8 124.8(2) . . ? O3 C1 C2 115.0(2) . . ? C8 C1 C2 120.1(2) . . ? C7 C2 C3 118.5(2) . . ? C7 C2 C1 121.6(2) . . ? C3 C2 C1 119.9(2) . . ? C4 C3 C2 120.6(3) . . ? C5 C4 C3 120.0(3) . . ? C6 C5 C4 119.8(3) . . ? C5 C6 C7 120.7(3) . . ? C6 C7 C2 120.4(3) . . ? C1 C8 C9 122.5(2) . . ? N1 C9 O1 115.1(2) . . ? N1 C9 C8 128.3(2) . . ? O1 C9 C8 116.6(2) . . ? O1 C10 C11 104.40(19) . . ? N1 C11 C13 111.49(19) . . ? N1 C11 C10 100.86(19) . . ? C13 C11 C10 112.2(2) . . ? N1 C11 C12 109.6(2) . . ? C13 C11 C12 111.6(2) . . ? C10 C11 C12 110.7(2) . . ? O4 C14 C21 124.8(2) . . ? O4 C14 C15 115.2(2) . . ? C21 C14 C15 120.0(2) . . ? C16 C15 C20 118.7(2) . . ? C16 C15 C14 120.0(2) . . ? C20 C15 C14 121.3(2) . . ? C15 C16 C17 120.2(3) . . ? C18 C17 C16 120.2(3) . . ? C19 C18 C17 119.9(3) . . ? C18 C19 C20 119.9(3) . . ? C19 C20 C15 121.0(2) . . ? C14 C21 C22 122.0(2) . . ? N2 C22 O2 115.3(2) . . ? N2 C22 C21 128.7(2) . . ? O2 C22 C21 116.0(2) . . ? O2 C23 C24 105.4(2) . . ? N2 C24 C25 110.7(2) . . ? N2 C24 C26 108.9(2) . . ? C25 C24 C26 111.9(2) . . ? N2 C24 C23 101.2(2) . . ? C25 C24 C23 111.7(2) . . ? C26 C24 C23 111.9(2) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.567 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.080