# Electronic Supplementary Material (ESI) for Chemical Communications # 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_jm0199j _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_absolute_configuration syn _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 O3,C6 H14 N' _chemical_formula_sum 'C20 H27 N O3' _chemical_formula_weight 329.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 15.9309(14) _cell_length_b 6.3941(6) _cell_length_c 18.8138(16) _cell_angle_alpha 90.00 _cell_angle_beta 107.606(3) _cell_angle_gamma 90.00 _cell_volume 1826.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.9650 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details sadbas _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II' _diffrn_measurement_method 'Phi-Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25915 _diffrn_reflns_av_R_equivalents 0.1153 _diffrn_reflns_av_sigmaI/netI 0.1761 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 28.35 _reflns_number_total 8305 _reflns_number_gt 3233 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 2.3' _computing_publication_material 'Shelxl 97' _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^)+(0.1000P)^2^+0.1065P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 8305 _refine_ls_number_parameters 439 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2234 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.2305 _refine_ls_wR_factor_gt 0.1413 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2965(4) 0.3633(12) 0.9430(4) 0.073(2) Uani 1 1 d . . . H1A H 0.3050 0.4728 0.9110 0.110 Uiso 1 1 calc R . . H1B H 0.3396 0.3759 0.9911 0.110 Uiso 1 1 calc R . . H1C H 0.2385 0.3746 0.9482 0.110 Uiso 1 1 calc R . . C2 C 0.3850(3) 0.1287(10) 0.9006(3) 0.0497(14) Uani 1 1 d . . . C3 C 0.3888(4) -0.0642(11) 0.8665(3) 0.0641(17) Uani 1 1 d . . . H3 H 0.3399 -0.1520 0.8543 0.077 Uiso 1 1 calc R . . C4 C 0.4633(4) -0.1240(9) 0.8512(3) 0.0584(16) Uani 1 1 d . . . H4 H 0.4649 -0.2528 0.8287 0.070 Uiso 1 1 calc R . . C5 C 0.5386(3) 0.0069(8) 0.8691(3) 0.0426(13) Uani 1 1 d . . . C6 C 0.5338(3) 0.2000(9) 0.9044(3) 0.0477(14) Uani 1 1 d . . . C7 C 0.4550(3) 0.2585(9) 0.9200(3) 0.0484(14) Uani 1 1 d . . . H7 H 0.4517 0.3850 0.9434 0.058 Uiso 1 1 calc R . . C8 C 0.6080(3) 0.3303(9) 0.9222(3) 0.0527(15) Uani 1 1 d . . . H8 H 0.6065 0.4576 0.9457 0.063 Uiso 1 1 calc R . . C9 C 0.6828(3) 0.2732(8) 0.9054(3) 0.0511(15) Uani 1 1 d . . . H9 H 0.7307 0.3637 0.9174 0.061 Uiso 1 1 calc R . . C10 C 0.6891(3) 0.0800(8) 0.8704(3) 0.0376(12) Uani 1 1 d . . . C11 C 0.6166(3) -0.0483(9) 0.8533(3) 0.0460(13) Uani 1 1 d . . . H11 H 0.6191 -0.1761 0.8305 0.055 Uiso 1 1 calc R . . C12 C 0.7741(3) 0.0229(8) 0.8538(3) 0.0387(12) Uani 1 1 d . . . H12 H 0.8036 0.1542 0.8489 0.046 Uiso 1 1 calc R . . C13 C 0.7589(4) -0.0975(10) 0.7804(3) 0.0601(17) Uani 1 1 d . . . H13A H 0.7373 -0.2352 0.7854 0.090 Uiso 1 1 calc R . . H13B H 0.8134 -0.1083 0.7687 0.090 Uiso 1 1 calc R . . H13C H 0.7164 -0.0245 0.7410 0.090 Uiso 1 1 calc R . . C14 C 0.8369(3) -0.0992(8) 0.9183(3) 0.0379(12) Uani 1 1 d . . . C15 C 0.3982(4) -0.1244(10) 0.3087(4) 0.081(2) Uani 1 1 d . . . H15A H 0.3816 -0.1760 0.3505 0.121 Uiso 1 1 calc R . . H15B H 0.4494 -0.1981 0.3055 0.121 Uiso 1 1 calc R . . H15C H 0.3506 -0.1458 0.2638 0.121 Uiso 1 1 calc R . . C16 C 0.4906(3) 0.1484(10) 0.3749(3) 0.0551(16) Uani 1 1 d . . . C17 C 0.5351(3) 0.0222(9) 0.4311(3) 0.0490(14) Uani 1 1 d . . . H17 H 0.5151 -0.1130 0.4346 0.059 Uiso 1 1 calc R . . C18 C 0.6126(3) 0.0967(8) 0.4848(3) 0.0404(13) Uani 1 1 d . . . C19 C 0.6409(3) 0.3018(8) 0.4790(3) 0.0432(13) Uani 1 1 d . . . C20 C 0.5903(3) 0.4300(9) 0.4197(3) 0.0557(15) Uani 1 1 d . . . H20 H 0.6074 0.5676 0.4161 0.067 Uiso 1 1 calc R . . C21 C 0.5179(4) 0.3542(9) 0.3689(3) 0.0595(16) Uani 1 1 d . . . H21 H 0.4860 0.4385 0.3297 0.071 Uiso 1 1 calc R . . C22 C 0.6637(3) -0.0309(9) 0.5423(3) 0.0446(13) Uani 1 1 d . . . H22 H 0.6443 -0.1646 0.5488 0.054 Uiso 1 1 calc R . . C23 C 0.7424(3) 0.0407(8) 0.5889(3) 0.0451(13) Uani 1 1 d . . . H23 H 0.7772 -0.0494 0.6246 0.054 Uiso 1 1 calc R . . C24 C 0.7718(3) 0.2449(8) 0.5844(3) 0.0386(12) Uani 1 1 d . . . C25 C 0.7198(3) 0.3751(8) 0.5295(3) 0.0434(13) Uani 1 1 d . . . H25 H 0.7374 0.5125 0.5260 0.052 Uiso 1 1 calc R . . C26 C 0.8582(3) 0.3231(8) 0.6384(3) 0.0439(13) Uani 1 1 d . . . H26 H 0.8937 0.2003 0.6599 0.053 Uiso 1 1 calc R . . C27 C 0.8420(4) 0.4469(11) 0.7025(3) 0.0659(17) Uani 1 1 d . . . H27A H 0.8157 0.3572 0.7307 0.099 Uiso 1 1 calc R . . H27B H 0.8032 0.5618 0.6827 0.099 Uiso 1 1 calc R . . H27C H 0.8970 0.4996 0.7343 0.099 Uiso 1 1 calc R . . C28 C 0.9097(3) 0.4494(10) 0.5964(3) 0.0465(13) Uani 1 1 d . . . C29 C 0.7266(5) 0.7804(12) 0.3241(4) 0.091(2) Uani 1 1 d . . . H29A H 0.7158 0.6511 0.2959 0.110 Uiso 1 1 calc R . . H29B H 0.6779 0.8025 0.3442 0.110 Uiso 1 1 calc R . . C30 C 0.7303(4) 0.9559(12) 0.2737(4) 0.0770(19) Uani 1 1 d . . . H30A H 0.6743 0.9679 0.2348 0.092 Uiso 1 1 calc R . . H30B H 0.7757 0.9293 0.2502 0.092 Uiso 1 1 calc R . . C31 C 0.7500(4) 1.1564(12) 0.3175(4) 0.078(2) Uani 1 1 d . . . H31A H 0.7014 1.1893 0.3365 0.094 Uiso 1 1 calc R . . H31B H 0.7553 1.2692 0.2846 0.094 Uiso 1 1 calc R . . C32 C 0.8339(4) 1.1426(10) 0.3819(3) 0.0685(18) Uani 1 1 d . . . H32A H 0.8423 1.2718 0.4102 0.082 Uiso 1 1 calc R . . H32B H 0.8836 1.1254 0.3627 0.082 Uiso 1 1 calc R . . C33 C 0.8311(3) 0.9612(9) 0.4327(3) 0.0492(14) Uani 1 1 d . . . H33 H 0.7830 0.9861 0.4539 0.059 Uiso 1 1 calc R . . C34 C 0.8119(5) 0.7605(9) 0.3883(4) 0.076(2) Uani 1 1 d . . . H34A H 0.8067 0.6462 0.4206 0.092 Uiso 1 1 calc R . . H34B H 0.8602 0.7291 0.3686 0.092 Uiso 1 1 calc R . . C35 C 0.0860(5) 0.7525(10) 0.7943(4) 0.074(2) Uani 1 1 d . . . H35A H 0.1495 0.7545 0.8050 0.089 Uiso 1 1 calc R . . H35B H 0.0635 0.6304 0.7639 0.089 Uiso 1 1 calc R . . C36 C 0.0477(4) 0.9456(11) 0.7521(3) 0.0708(18) Uani 1 1 d . . . H36A H -0.0161 0.9369 0.7371 0.085 Uiso 1 1 calc R . . H36B H 0.0656 0.9546 0.7073 0.085 Uiso 1 1 calc R . . C37 C 0.0770(5) 1.1390(10) 0.7981(4) 0.0698(18) Uani 1 1 d . . . H37A H 0.0480 1.2603 0.7704 0.084 Uiso 1 1 calc R . . H37B H 0.1400 1.1566 0.8084 0.084 Uiso 1 1 calc R . . C38 C 0.0549(4) 1.1240(9) 0.8714(3) 0.0587(16) Uani 1 1 d . . . H38A H 0.0781 1.2452 0.9020 0.070 Uiso 1 1 calc R . . H38B H -0.0085 1.1221 0.8614 0.070 Uiso 1 1 calc R . . C39 C 0.0942(3) 0.9282(9) 0.9121(3) 0.0451(13) Uani 1 1 d . . . H39 H 0.1583 0.9365 0.9231 0.054 Uiso 1 1 calc R . . C40 C 0.0632(4) 0.7370(8) 0.8669(3) 0.0582(16) Uani 1 1 d . . . H40A H 0.0000 0.7228 0.8563 0.070 Uiso 1 1 calc R . . H40B H 0.0911 0.6145 0.8945 0.070 Uiso 1 1 calc R . . O1 O 0.4172(3) 0.0910(7) 0.3182(3) 0.0800(14) Uani 1 1 d . . . O2 O 0.9091(3) 0.6417(6) 0.5990(2) 0.0620(11) Uani 1 1 d . . . O3 O 0.9492(3) 0.3437(7) 0.5598(2) 0.0691(12) Uani 1 1 d . . . O4 O 0.3056(2) 0.1662(7) 0.9115(2) 0.0676(12) Uani 1 1 d . . . O5 O 0.8943(2) 0.0038(5) 0.9666(2) 0.0522(10) Uani 1 1 d . . . O6 O 0.8280(3) -0.2892(6) 0.9204(2) 0.0641(12) Uani 1 1 d . . . N1 N 0.0735(3) 0.9173(7) 0.9854(2) 0.0468(11) Uani 1 1 d . . . H1D H 0.0877 0.7915 1.0056 0.070 Uiso 1 1 calc R . . H1E H 0.0162 0.9396 0.9774 0.070 Uiso 1 1 calc R . . H1F H 0.1043 1.0145 1.0163 0.070 Uiso 1 1 calc R . . N2 N 0.9153(3) 0.9485(7) 0.4957(2) 0.0493(11) Uani 1 1 d . . . H2A H 0.9601 0.9277 0.4774 0.074 Uiso 1 1 calc R . . H2B H 0.9122 0.8427 0.5255 0.074 Uiso 1 1 calc R . . H2C H 0.9236 1.0674 0.5214 0.074 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.052(4) 0.106(6) 0.064(4) -0.006(4) 0.023(3) 0.010(4) C2 0.036(3) 0.066(4) 0.046(3) 0.002(3) 0.011(3) 0.004(3) C3 0.043(3) 0.069(4) 0.079(4) -0.004(4) 0.015(3) -0.011(3) C4 0.053(4) 0.049(4) 0.069(4) -0.017(3) 0.013(3) -0.014(3) C5 0.042(3) 0.044(3) 0.042(3) 0.002(3) 0.013(2) 0.002(2) C6 0.047(3) 0.046(3) 0.044(3) -0.004(3) 0.005(3) -0.001(3) C7 0.041(3) 0.056(4) 0.050(4) -0.007(3) 0.018(3) 0.002(3) C8 0.045(3) 0.049(3) 0.064(4) -0.016(3) 0.018(3) -0.006(3) C9 0.047(3) 0.040(3) 0.062(4) -0.006(3) 0.010(3) -0.007(3) C10 0.039(3) 0.041(3) 0.031(3) 0.003(2) 0.008(2) 0.003(2) C11 0.053(3) 0.037(3) 0.042(3) -0.005(3) 0.005(2) -0.003(3) C12 0.045(3) 0.031(3) 0.038(3) 0.001(2) 0.008(2) 0.001(2) C13 0.059(3) 0.084(5) 0.036(3) -0.002(3) 0.012(3) 0.013(3) C14 0.037(3) 0.039(3) 0.036(3) 0.000(2) 0.009(2) 0.000(2) C15 0.077(4) 0.065(5) 0.083(5) -0.013(4) -0.001(4) -0.015(4) C16 0.046(3) 0.052(4) 0.057(4) -0.006(3) -0.001(3) 0.008(3) C17 0.047(3) 0.042(3) 0.057(4) 0.000(3) 0.014(3) -0.001(3) C18 0.045(3) 0.034(3) 0.042(3) 0.001(2) 0.013(3) -0.001(2) C19 0.044(3) 0.041(3) 0.046(3) -0.005(3) 0.015(3) 0.003(3) C20 0.052(3) 0.039(3) 0.068(4) 0.008(3) 0.005(3) 0.003(3) C21 0.056(4) 0.045(4) 0.065(4) 0.003(3) -0.001(3) 0.002(3) C22 0.052(3) 0.039(3) 0.045(3) 0.005(3) 0.018(3) -0.006(3) C23 0.056(3) 0.040(3) 0.041(3) 0.007(3) 0.017(3) 0.008(3) C24 0.043(3) 0.041(3) 0.034(3) 0.003(2) 0.015(2) 0.001(2) C25 0.048(3) 0.032(3) 0.049(3) 0.001(2) 0.014(3) 0.001(2) C26 0.049(3) 0.040(3) 0.042(3) 0.003(3) 0.014(3) 0.002(3) C27 0.073(4) 0.081(5) 0.046(3) -0.013(4) 0.023(3) -0.013(4) C28 0.053(3) 0.044(3) 0.042(3) -0.002(3) 0.012(3) -0.005(3) C29 0.097(5) 0.085(6) 0.076(5) -0.011(5) 0.002(4) -0.021(5) C30 0.088(5) 0.080(5) 0.059(4) 0.001(4) 0.016(3) -0.007(4) C31 0.089(5) 0.077(5) 0.061(4) 0.011(4) 0.012(4) 0.027(4) C32 0.106(5) 0.038(3) 0.061(4) 0.008(3) 0.026(4) 0.006(3) C33 0.053(3) 0.047(3) 0.050(3) 0.003(3) 0.019(3) 0.008(3) C34 0.121(6) 0.034(3) 0.076(5) 0.010(3) 0.031(4) -0.008(3) C35 0.118(6) 0.050(4) 0.061(4) 0.003(3) 0.037(4) 0.010(4) C36 0.094(5) 0.062(4) 0.059(4) 0.006(4) 0.026(3) 0.003(4) C37 0.097(5) 0.047(4) 0.063(4) 0.014(3) 0.021(4) -0.007(4) C38 0.072(4) 0.035(3) 0.062(4) 0.003(3) 0.009(3) 0.001(3) C39 0.049(3) 0.039(3) 0.044(3) -0.001(3) 0.008(2) 0.001(3) C40 0.081(4) 0.032(3) 0.058(4) -0.003(3) 0.016(3) 0.000(3) O1 0.065(3) 0.056(3) 0.091(3) 0.000(2) -0.019(2) 0.001(2) O2 0.085(3) 0.046(3) 0.059(3) 0.005(2) 0.028(2) -0.002(2) O3 0.069(3) 0.068(3) 0.087(3) -0.021(2) 0.048(2) -0.017(2) O4 0.047(2) 0.083(3) 0.078(3) -0.012(3) 0.025(2) -0.002(2) O5 0.048(2) 0.044(2) 0.055(2) -0.0065(19) 0.0010(18) 0.0013(18) O6 0.068(3) 0.035(2) 0.070(3) 0.011(2) -0.008(2) -0.0025(19) N1 0.046(2) 0.034(2) 0.052(3) -0.005(2) 0.004(2) 0.002(2) N2 0.062(3) 0.039(2) 0.051(3) 0.005(2) 0.022(2) 0.004(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 C1 O4 1.419(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C7 1.349(7) . ? C2 O4 1.361(6) . ? C2 C3 1.399(8) . ? C3 C4 1.358(8) . ? C3 H3 0.9300 . ? C4 C5 1.418(7) . ? C4 H4 0.9300 . ? C5 C11 1.406(7) . ? C5 C6 1.415(7) . ? C6 C8 1.402(7) . ? C6 C7 1.424(7) . ? C7 H7 0.9300 . ? C8 C9 1.371(7) . ? C8 H8 0.9300 . ? C9 C10 1.418(7) . ? C9 H9 0.9300 . ? C10 C11 1.374(7) . ? C10 C12 1.522(7) . ? C11 H11 0.9300 . ? C12 C14 1.532(6) . ? C12 C13 1.536(7) . ? C12 H12 0.9800 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 O6 1.225(6) . ? C14 O5 1.262(6) . ? C15 O1 1.410(8) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.348(7) . ? C16 O1 1.373(6) . ? C16 C21 1.401(8) . ? C17 C18 1.421(7) . ? C17 H17 0.9300 . ? C18 C19 1.402(7) . ? C18 C22 1.402(7) . ? C19 C25 1.407(7) . ? C19 C20 1.422(7) . ? C20 C21 1.346(7) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.373(7) . ? C22 H22 0.9300 . ? C23 C24 1.399(7) . ? C23 H23 0.9300 . ? C24 C25 1.389(7) . ? C24 C26 1.527(7) . ? C25 H25 0.9300 . ? C26 C27 1.528(7) . ? C26 C28 1.530(7) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 O2 1.231(7) 1 ? C28 O2 1.231(7) . ? C28 O3 1.261(6) . ? C29 C30 1.482(10) . ? C29 C34 1.525(9) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.504(10) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.511(9) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.512(8) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 N2 1.499(6) . ? C33 C34 1.511(8) . ? C33 H33 0.9800 . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.496(9) . ? C35 C40 1.518(9) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.501(9) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.525(9) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.502(7) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.486(8) . ? C39 N1 1.514(6) . ? C39 H39 0.9800 . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? O2 O2 0.000(11) 1 ? N1 H1D 0.8900 . ? N1 H1E 0.8900 . ? N1 H1F 0.8900 . ? N2 H2A 0.8900 . ? N2 H2B 0.8900 . ? N2 H2C 0.8900 . ? 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 C1 H1A 109.5 . . ? O4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 O4 125.4(5) . . ? C7 C2 C3 121.3(5) . . ? O4 C2 C3 113.3(5) . . ? C4 C3 C2 120.5(5) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 121.0(5) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C11 C5 C6 119.7(5) . . ? C11 C5 C4 122.7(5) . . ? C6 C5 C4 117.6(5) . . ? C8 C6 C5 118.0(5) . . ? C8 C6 C7 121.8(5) . . ? C5 C6 C7 120.2(5) . . ? C2 C7 C6 119.4(5) . . ? C2 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C9 C8 C6 121.1(5) . . ? C9 C8 H8 119.5 . . ? C6 C8 H8 119.5 . . ? C8 C9 C10 121.9(5) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C11 C10 C9 117.1(5) . . ? C11 C10 C12 123.1(5) . . ? C9 C10 C12 119.8(5) . . ? C10 C11 C5 122.4(5) . . ? C10 C11 H11 118.8 . . ? C5 C11 H11 118.8 . . ? C10 C12 C14 111.6(4) . . ? C10 C12 C13 113.4(4) . . ? C14 C12 C13 110.2(4) . . ? C10 C12 H12 107.1 . . ? C14 C12 H12 107.1 . . ? C13 C12 H12 107.1 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O6 C14 O5 124.1(5) . . ? O6 C14 C12 118.5(4) . . ? O5 C14 C12 117.4(4) . . ? O1 C15 H15A 109.5 . . ? O1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 O1 124.8(6) . . ? C17 C16 C21 121.6(5) . . ? O1 C16 C21 113.6(5) . . ? C16 C17 C18 119.6(5) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C19 C18 C22 118.6(5) . . ? C19 C18 C17 119.3(5) . . ? C22 C18 C17 122.1(5) . . ? C18 C19 C25 120.1(5) . . ? C18 C19 C20 118.7(5) . . ? C25 C19 C20 121.1(5) . . ? C21 C20 C19 120.7(6) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C16 120.1(5) . . ? C20 C21 H21 120.0 . . ? C16 C21 H21 120.0 . . ? C23 C22 C18 120.3(5) . . ? C23 C22 H22 119.8 . . ? C18 C22 H22 119.8 . . ? C22 C23 C24 122.0(5) . . ? C22 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C25 C24 C23 118.0(5) . . ? C25 C24 C26 120.9(5) . . ? C23 C24 C26 121.0(5) . . ? C24 C25 C19 120.8(5) . . ? C24 C25 H25 119.6 . . ? C19 C25 H25 119.6 . . ? C24 C26 C27 111.2(4) . . ? C24 C26 C28 110.1(4) . . ? C27 C26 C28 112.3(5) . . ? C24 C26 H26 107.7 . . ? C27 C26 H26 107.7 . . ? C28 C26 H26 107.7 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O2 C28 O2 0.0(4) 1 . ? O2 C28 O3 124.6(5) 1 . ? O2 C28 O3 124.6(5) . . ? O2 C28 C26 119.7(5) 1 . ? O2 C28 C26 119.7(5) . . ? O3 C28 C26 115.7(5) . . ? C30 C29 C34 111.8(6) . . ? C30 C29 H29A 109.3 . . ? C34 C29 H29A 109.3 . . ? C30 C29 H29B 109.3 . . ? C34 C29 H29B 109.3 . . ? H29A C29 H29B 107.9 . . ? C29 C30 C31 109.7(5) . . ? C29 C30 H30A 109.7 . . ? C31 C30 H30A 109.7 . . ? C29 C30 H30B 109.7 . . ? C31 C30 H30B 109.7 . . ? H30A C30 H30B 108.2 . . ? C30 C31 C32 112.1(6) . . ? C30 C31 H31A 109.2 . . ? C32 C31 H31A 109.2 . . ? C30 C31 H31B 109.2 . . ? C32 C31 H31B 109.2 . . ? H31A C31 H31B 107.9 . . ? C31 C32 C33 111.3(6) . . ? C31 C32 H32A 109.4 . . ? C33 C32 H32A 109.4 . . ? C31 C32 H32B 109.4 . . ? C33 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? N2 C33 C34 112.0(5) . . ? N2 C33 C32 110.6(5) . . ? C34 C33 C32 110.0(5) . . ? N2 C33 H33 108.1 . . ? C34 C33 H33 108.1 . . ? C32 C33 H33 108.1 . . ? C33 C34 C29 110.5(6) . . ? C33 C34 H34A 109.6 . . ? C29 C34 H34A 109.6 . . ? C33 C34 H34B 109.6 . . ? C29 C34 H34B 109.6 . . ? H34A C34 H34B 108.1 . . ? C36 C35 C40 111.2(5) . . ? C36 C35 H35A 109.4 . . ? C40 C35 H35A 109.4 . . ? C36 C35 H35B 109.4 . . ? C40 C35 H35B 109.4 . . ? H35A C35 H35B 108.0 . . ? C35 C36 C37 111.6(5) . . ? C35 C36 H36A 109.3 . . ? C37 C36 H36A 109.3 . . ? C35 C36 H36B 109.3 . . ? C37 C36 H36B 109.3 . . ? H36A C36 H36B 108.0 . . ? C36 C37 C38 110.7(5) . . ? C36 C37 H37A 109.5 . . ? C38 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? C38 C37 H37B 109.5 . . ? H37A C37 H37B 108.1 . . ? C39 C38 C37 109.8(5) . . ? C39 C38 H38A 109.7 . . ? C37 C38 H38A 109.7 . . ? C39 C38 H38B 109.7 . . ? C37 C38 H38B 109.7 . . ? H38A C38 H38B 108.2 . . ? C40 C39 C38 112.3(4) . . ? C40 C39 N1 110.9(5) . . ? C38 C39 N1 109.3(4) . . ? C40 C39 H39 108.1 . . ? C38 C39 H39 108.1 . . ? N1 C39 H39 108.1 . . ? C39 C40 C35 109.4(5) . . ? C39 C40 H40A 109.8 . . ? C35 C40 H40A 109.8 . . ? C39 C40 H40B 109.8 . . ? C35 C40 H40B 109.8 . . ? H40A C40 H40B 108.2 . . ? C16 O1 C15 117.4(5) . . ? O2 O2 C28 0(10) 1 . ? C2 O4 C1 115.9(5) . . ? C39 N1 H1D 109.5 . . ? C39 N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? C39 N1 H1F 109.5 . . ? H1D N1 H1F 109.5 . . ? H1E N1 H1F 109.5 . . ? C33 N2 H2A 109.5 . . ? C33 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C33 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? 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 H1D O5 0.89 1.91 2.791(5) 170.3 2_657 N1 H1E O5 0.89 1.93 2.823(5) 175.4 1_465 N1 H1F O6 0.89 1.84 2.728(5) 177.7 2_667 N2 H2A O3 0.89 1.87 2.749(6) 171.9 2_756 N2 H2B O2 0.89 1.90 2.785(6) 172.9 1 N2 H2C O3 0.89 1.91 2.782(6) 168.0 1_565 _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.244 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 944131' ####################################################################### # # 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_jmnpbs _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_absolute_configuration syn _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 O3, C7 H10 N' _chemical_formula_sum 'C21 H23 N O3' _chemical_formula_weight 337.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.632(4) _cell_length_b 5.9372(19) _cell_length_c 13.377(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.327(5) _cell_angle_gamma 90.00 _cell_volume 923.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9569 _exptl_absorpt_correction_T_max 0.9968 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II' _diffrn_measurement_method 'Phi-Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7466 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_sigmaI/netI 0.1472 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 27.36 _reflns_number_total 3685 _reflns_number_gt 1546 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 2.3' _computing_publication_material 'Shelxl 97' _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^)+(0.1000P)^2^+0.7826P] 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 3685 _refine_ls_number_parameters 229 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1908 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.2198 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 0.836 _refine_ls_restrained_S_all 0.836 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.2495(6) 0.4670(14) 0.5801(5) 0.078(2) Uani 1 1 d . . . H1A H -0.2202 0.5929 0.6173 0.117 Uiso 1 1 calc R . . H1B H -0.3319 0.4763 0.5765 0.117 Uiso 1 1 calc R . . H1C H -0.2185 0.4694 0.5138 0.117 Uiso 1 1 calc R . . C2 C -0.1022(6) 0.2197(11) 0.6422(4) 0.0553(16) Uani 1 1 d . . . C3 C -0.0785(6) 0.0147(11) 0.6921(4) 0.0609(17) Uani 1 1 d . . . H3 H -0.1389 -0.0772 0.7121 0.073 Uiso 1 1 calc R . . C4 C 0.0309(6) -0.0490(11) 0.7111(4) 0.0603(17) Uani 1 1 d . . . H4 H 0.0443 -0.1856 0.7431 0.072 Uiso 1 1 calc R . . C5 C 0.1262(5) 0.0874(10) 0.6835(4) 0.0488(15) Uani 1 1 d . . . C6 C 0.1025(5) 0.2919(9) 0.6337(4) 0.0468(15) Uani 1 1 d . . . C7 C -0.0132(5) 0.3536(11) 0.6121(4) 0.0566(17) Uani 1 1 d . . . H7 H -0.0284 0.4860 0.5773 0.068 Uiso 1 1 calc R . . C8 C 0.1969(5) 0.4301(11) 0.6096(4) 0.0585(17) Uani 1 1 d . . . H8 H 0.1837 0.5659 0.5768 0.070 Uiso 1 1 calc R . . C9 C 0.3062(6) 0.3709(10) 0.6330(4) 0.0549(16) Uani 1 1 d . . . H9 H 0.3662 0.4673 0.6164 0.066 Uiso 1 1 calc R . . C10 C 0.3314(5) 0.1647(9) 0.6823(4) 0.0441(14) Uani 1 1 d . . . C11 C 0.2411(5) 0.0299(10) 0.7058(4) 0.0493(15) Uani 1 1 d . . . H11 H 0.2558 -0.1061 0.7379 0.059 Uiso 1 1 calc R . . C12 C 0.4575(5) 0.1052(9) 0.7027(4) 0.0465(15) Uani 1 1 d . . . H12 H 0.4984 0.2444 0.7198 0.056 Uiso 1 1 calc R . . C13 C 0.5123(5) 0.0063(12) 0.6088(4) 0.0647(18) Uani 1 1 d . . . H13A H 0.4757 -0.1340 0.5925 0.097 Uiso 1 1 calc R . . H13B H 0.5927 -0.0189 0.6207 0.097 Uiso 1 1 calc R . . H13C H 0.5029 0.1096 0.5542 0.097 Uiso 1 1 calc R . . C14 C 0.4678(5) -0.0552(10) 0.7912(4) 0.0449(14) Uani 1 1 d . . . C15 C 0.2388(6) 0.3039(12) -0.0045(4) 0.0631(19) Uani 1 1 d . . . C16 C 0.2714(6) 0.2350(16) 0.0907(5) 0.083(2) Uani 1 1 d . . . H16 H 0.3289 0.3125 0.1248 0.100 Uiso 1 1 calc R . . C17 C 0.2193(7) 0.0536(15) 0.1345(5) 0.093(3) Uani 1 1 d . . . H17 H 0.2427 0.0055 0.1976 0.111 Uiso 1 1 calc R . . C18 C 0.1330(6) -0.0564(14) 0.0852(5) 0.079(2) Uani 1 1 d . . . H18 H 0.0967 -0.1779 0.1155 0.095 Uiso 1 1 calc R . . C19 C 0.0995(6) 0.0094(15) -0.0072(5) 0.085(2) Uani 1 1 d . . . H19 H 0.0406 -0.0668 -0.0401 0.102 Uiso 1 1 calc R . . C20 C 0.1524(6) 0.1889(14) -0.0524(5) 0.073(2) Uani 1 1 d . . . H20 H 0.1294 0.2329 -0.1161 0.088 Uiso 1 1 calc R . . C21 C 0.2957(6) 0.5005(13) -0.0567(5) 0.075(2) Uani 1 1 d . . . H21A H 0.2612 0.5205 -0.1222 0.090 Uiso 1 1 calc R . . H21B H 0.2827 0.6369 -0.0185 0.090 Uiso 1 1 calc R . . N1 N 0.4222(4) 0.4638(8) -0.0677(3) 0.0514(13) Uani 1 1 d . . . H1D H 0.4563 0.4760 -0.0083 0.077 Uiso 1 1 calc R . . H1E H 0.4508 0.5666 -0.1091 0.077 Uiso 1 1 calc R . . H1F H 0.4347 0.3268 -0.0924 0.077 Uiso 1 1 calc R . . O1 O -0.2171(4) 0.2628(8) 0.6287(3) 0.0698(13) Uani 1 1 d . . . O2 O 0.4749(4) -0.2600(7) 0.7766(3) 0.0639(12) Uani 1 1 d . . . O3 O 0.4696(4) 0.0330(6) 0.8785(3) 0.0582(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.080(5) 0.079(5) 0.075(4) 0.003(4) -0.015(4) 0.007(5) C2 0.062(5) 0.052(4) 0.052(4) -0.006(3) -0.006(3) -0.008(4) C3 0.061(5) 0.046(4) 0.075(4) 0.008(3) -0.003(3) -0.013(4) C4 0.065(5) 0.046(4) 0.070(4) 0.012(3) -0.002(3) -0.006(4) C5 0.058(4) 0.045(4) 0.044(3) -0.001(3) -0.003(3) -0.003(3) C6 0.058(4) 0.037(4) 0.045(3) 0.001(3) -0.007(3) -0.001(3) C7 0.071(5) 0.046(4) 0.052(3) 0.004(3) -0.004(3) 0.005(4) C8 0.071(5) 0.044(4) 0.061(4) 0.016(3) -0.005(3) -0.008(4) C9 0.062(4) 0.043(4) 0.059(3) 0.015(3) -0.002(3) -0.010(3) C10 0.054(4) 0.040(4) 0.038(3) 0.001(3) 0.000(3) -0.002(3) C11 0.061(4) 0.038(3) 0.049(3) 0.005(3) -0.004(3) -0.003(3) C12 0.059(4) 0.037(3) 0.044(3) 0.005(3) -0.004(3) -0.006(3) C13 0.076(4) 0.071(5) 0.047(3) 0.007(3) 0.006(3) 0.005(4) C14 0.054(4) 0.041(4) 0.040(3) 0.004(3) -0.002(2) 0.006(3) C15 0.059(4) 0.078(5) 0.052(4) 0.002(4) 0.012(3) 0.015(4) C16 0.079(5) 0.106(6) 0.064(4) 0.007(4) -0.011(4) -0.016(5) C17 0.096(6) 0.114(8) 0.068(4) 0.029(5) -0.004(4) -0.027(6) C18 0.067(5) 0.082(6) 0.089(5) 0.009(5) 0.023(4) -0.003(5) C19 0.087(6) 0.091(6) 0.076(5) -0.003(5) -0.010(4) -0.014(5) C20 0.068(5) 0.094(6) 0.058(4) 0.000(4) -0.009(3) 0.005(5) C21 0.070(5) 0.072(5) 0.083(4) 0.016(4) 0.009(4) 0.017(4) N1 0.078(4) 0.031(3) 0.045(2) -0.001(2) 0.000(2) 0.000(3) O1 0.062(3) 0.071(3) 0.076(3) 0.002(3) -0.009(2) -0.001(3) O2 0.104(3) 0.034(3) 0.053(2) 0.0014(19) -0.011(2) -0.003(2) O3 0.087(3) 0.044(2) 0.043(2) -0.0020(19) -0.0048(19) 0.014(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 C1 O1 1.425(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C7 1.368(8) . ? C2 O1 1.372(7) . ? C2 C3 1.415(9) . ? C3 C4 1.350(8) . ? C3 H3 0.9300 . ? C4 C5 1.423(8) . ? C4 H4 0.9300 . ? C5 C11 1.410(8) . ? C5 C6 1.411(7) . ? C6 C8 1.409(8) . ? C6 C7 1.423(8) . ? C7 H7 0.9300 . ? C8 C9 1.355(8) . ? C8 H8 0.9300 . ? C9 C10 1.420(8) . ? C9 H9 0.9300 . ? C10 C11 1.358(7) . ? C10 C12 1.531(8) . ? C11 H11 0.9300 . ? C12 C14 1.523(7) . ? C12 C13 1.530(7) . ? C12 H12 0.9800 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 O2 1.234(7) . ? C14 O3 1.281(6) . ? C15 C20 1.371(9) . ? C15 C16 1.388(8) . ? C15 C21 1.514(10) . ? C16 C17 1.370(11) . ? C16 H16 0.9300 . ? C17 C18 1.365(10) . ? C17 H17 0.9300 . ? C18 C19 1.351(9) . ? C18 H18 0.9300 . ? C19 C20 1.373(10) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 N1 1.495(7) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? N1 H1D 0.8900 . ? N1 H1E 0.8900 . ? N1 H1F 0.8900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 O1 126.2(6) . . ? C7 C2 C3 119.6(6) . . ? O1 C2 C3 114.2(6) . . ? C4 C3 C2 120.7(6) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 121.8(6) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C11 C5 C6 119.3(5) . . ? C11 C5 C4 123.1(5) . . ? C6 C5 C4 117.5(5) . . ? C8 C6 C5 117.3(5) . . ? C8 C6 C7 122.7(5) . . ? C5 C6 C7 119.9(5) . . ? C2 C7 C6 120.5(6) . . ? C2 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C9 C8 C6 121.8(6) . . ? C9 C8 H8 119.1 . . ? C6 C8 H8 119.1 . . ? C8 C9 C10 121.5(6) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C11 C10 C9 117.2(5) . . ? C11 C10 C12 124.3(5) . . ? C9 C10 C12 118.4(5) . . ? C10 C11 C5 122.8(5) . . ? C10 C11 H11 118.6 . . ? C5 C11 H11 118.6 . . ? C14 C12 C13 111.5(5) . . ? C14 C12 C10 110.7(4) . . ? C13 C12 C10 110.2(4) . . ? C14 C12 H12 108.1 . . ? C13 C12 H12 108.1 . . ? C10 C12 H12 108.1 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 O3 123.1(5) . . ? O2 C14 C12 119.9(5) . . ? O3 C14 C12 117.0(5) . . ? C20 C15 C16 118.5(7) . . ? C20 C15 C21 119.3(6) . . ? C16 C15 C21 122.1(7) . . ? C17 C16 C15 120.4(7) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C18 C17 C16 119.7(7) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C19 C18 C17 120.8(7) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 120.0(7) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C15 C20 C19 120.7(7) . . ? C15 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? N1 C21 C15 111.5(5) . . ? N1 C21 H21A 109.3 . . ? C15 C21 H21A 109.3 . . ? N1 C21 H21B 109.3 . . ? C15 C21 H21B 109.3 . . ? H21A C21 H21B 108.0 . . ? C21 N1 H1D 109.5 . . ? C21 N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? C21 N1 H1F 109.5 . . ? H1D N1 H1F 109.5 . . ? H1E N1 H1F 109.5 . . ? C2 O1 C1 118.3(5) . . ? 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 H1D O3 0.89 1.96 2.850(5) 174.8 2_656 N1 H1E O2 0.89 1.87 2.723(6) 161.2 1_564 N1 H1F O3 0.89 1.83 2.714(6) 170.1 1_554 _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.210 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.079 _database_code_depnum_ccdc_archive 'CCDC 947071' ####################################################################### # # 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_jm0198j_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration syn _chemical_formula_moiety 'C14 H13 O3, C14 H16 N' _chemical_formula_sum 'C28 H29 N O3' _chemical_formula_weight 427.52 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 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.7688(14) _cell_length_b 8.478(2) _cell_length_c 48.065(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2350.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.95 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9298 _exptl_absorpt_correction_T_max 0.9984 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II' _diffrn_measurement_method 'Phi-Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7900 _diffrn_reflns_av_R_equivalents 0.0663 _diffrn_reflns_av_sigmaI/netI 0.1134 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -54 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 0.85 _diffrn_reflns_theta_max 27.05 _reflns_number_total 2648 _reflns_number_gt 1358 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 2.3' _computing_publication_material 'Shelxl 97' _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^)+(0.1000P)^2^+0.7811P] 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 2648 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1564 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.2094 _refine_ls_wR_factor_gt 0.1512 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.496(2) -0.2591(13) 0.24729(19) 0.095(3) Uani 1 1 d . . . H1A H 0.4843 -0.3481 0.2350 0.142 Uiso 1 1 calc R . . H1B H 0.5127 -0.2955 0.2661 0.142 Uiso 1 1 calc R . . H1C H 0.6295 -0.1973 0.2423 0.142 Uiso 1 1 calc R . . C2 C 0.2590(14) -0.0872(11) 0.22068(19) 0.055(2) Uani 1 1 d . . . C3 C 0.0545(15) 0.0018(12) 0.2205(2) 0.073(3) Uani 1 1 d . . . H3 H -0.0388 0.0038 0.2363 0.087 Uiso 1 1 calc R . . C4 C -0.0092(13) 0.0846(11) 0.19776(19) 0.066(3) Uani 1 1 d . . . H4 H -0.1454 0.1432 0.1982 0.080 Uiso 1 1 calc R . . C5 C 0.1279(13) 0.0839(10) 0.17317(17) 0.050(2) Uani 1 1 d . . . C6 C 0.3385(12) -0.0030(10) 0.17371(16) 0.045(2) Uani 1 1 d . . . C7 C 0.3983(13) -0.0907(10) 0.19794(18) 0.053(2) Uani 1 1 d . . . H7 H 0.5333 -0.1506 0.1982 0.064 Uiso 1 1 calc R . . C8 C 0.4782(13) -0.0019(10) 0.14990(17) 0.055(2) Uani 1 1 d . . . H8 H 0.6170 -0.0577 0.1499 0.067 Uiso 1 1 calc R . . C9 C 0.4140(13) 0.0794(10) 0.12685(17) 0.056(2) Uani 1 1 d . . . H9 H 0.5123 0.0792 0.1115 0.068 Uiso 1 1 calc R . . C10 C 0.2050(13) 0.1640(9) 0.12522(16) 0.047(2) Uani 1 1 d . . . C11 C 0.0695(13) 0.1662(10) 0.14878(18) 0.057(2) Uani 1 1 d . . . H11 H -0.0668 0.2248 0.1486 0.068 Uiso 1 1 calc R . . C12 C 0.1270(13) 0.2481(10) 0.09930(16) 0.053(2) Uani 1 1 d . . . H12 H -0.0200 0.3002 0.1038 0.063 Uiso 1 1 calc R . . C13 C 0.0776(17) 0.1315(11) 0.07565(17) 0.090(3) Uani 1 1 d . . . H13A H 0.2180 0.0776 0.0707 0.135 Uiso 1 1 calc R . . H13B H 0.0197 0.1878 0.0598 0.135 Uiso 1 1 calc R . . H13C H -0.0360 0.0561 0.0817 0.135 Uiso 1 1 calc R . . C14 C 0.2971(16) 0.3787(14) 0.08982(16) 0.060(3) Uani 1 1 d . . . C15 C 0.5803(14) 0.5283(11) 0.14894(19) 0.068(3) Uani 1 1 d . . . H15 H 0.4454 0.5064 0.1391 0.082 Uiso 1 1 calc R . . C16 C 0.6088(15) 0.4654(12) 0.1754(2) 0.075(3) Uani 1 1 d . . . H16 H 0.4956 0.4005 0.1830 0.090 Uiso 1 1 calc R . . C17 C 0.8087(19) 0.5007(13) 0.19025(18) 0.077(3) Uani 1 1 d . . . H17 H 0.8295 0.4606 0.2081 0.093 Uiso 1 1 calc R . . C18 C 0.9755(17) 0.5951(13) 0.1785(2) 0.085(3) Uani 1 1 d . . . H18 H 1.1090 0.6188 0.1885 0.102 Uiso 1 1 calc R . . C19 C 0.9482(14) 0.6547(11) 0.1523(2) 0.069(3) Uani 1 1 d . . . H19 H 1.0644 0.7170 0.1446 0.083 Uiso 1 1 calc R . . C20 C 0.7491(14) 0.6235(10) 0.13688(17) 0.053(2) Uani 1 1 d . . . C21 C 0.7081(14) 0.6983(10) 0.10894(17) 0.064(2) Uani 1 1 d . . . H21A H 0.5447 0.7233 0.1072 0.077 Uiso 1 1 calc R . . H21B H 0.7939 0.7966 0.1080 0.077 Uiso 1 1 calc R . . C22 C 0.7503(15) 0.6821(10) 0.05802(17) 0.069(3) Uani 1 1 d . . . H22A H 0.5870 0.7041 0.0552 0.083 Uiso 1 1 calc R . . H22B H 0.8306 0.7824 0.0592 0.083 Uiso 1 1 calc R . . C23 C 0.8390(15) 0.5946(12) 0.03380(18) 0.058(2) Uani 1 1 d . . . C24 C 0.7100(16) 0.4797(12) 0.0211(2) 0.073(3) Uani 1 1 d . . . H24 H 0.5683 0.4508 0.0288 0.087 Uiso 1 1 calc R . . C25 C 0.786(2) 0.4056(13) -0.0029(2) 0.092(3) Uani 1 1 d . . . H25 H 0.6957 0.3265 -0.0108 0.110 Uiso 1 1 calc R . . C26 C 0.989(2) 0.4464(13) -0.0150(2) 0.089(3) Uani 1 1 d . . . H26 H 1.0342 0.4009 -0.0317 0.107 Uiso 1 1 calc R . . C27 C 1.1283(17) 0.5573(14) -0.0020(2) 0.082(3) Uani 1 1 d . . . H27 H 1.2742 0.5806 -0.0091 0.098 Uiso 1 1 calc R . . C28 C 1.0510(15) 0.6317(11) 0.0213(2) 0.069(3) Uani 1 1 d . . . H28 H 1.1424 0.7102 0.0291 0.083 Uiso 1 1 calc R . . N1 N 0.7784(9) 0.5963(8) 0.08498(12) 0.0545(19) Uani 1 1 d . . . H1D H 0.9274 0.5671 0.0870 0.065 Uiso 1 1 calc R . . H1E H 0.6907 0.5085 0.0848 0.065 Uiso 1 1 calc R . . O1 O 0.2972(10) -0.1668(8) 0.24504(12) 0.0760(19) Uani 1 1 d . . . O2 O 0.2283(9) 0.5187(8) 0.08800(11) 0.0675(19) Uani 1 1 d . . . O3 O 0.5005(9) 0.3344(7) 0.08359(11) 0.0692(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.098(7) 0.112(9) 0.075(7) 0.035(6) 0.006(6) 0.025(8) C2 0.059(6) 0.053(7) 0.053(6) -0.005(5) 0.003(5) 0.003(6) C3 0.065(6) 0.089(8) 0.063(7) 0.012(6) 0.019(5) 0.008(7) C4 0.054(5) 0.083(8) 0.063(6) 0.003(6) 0.022(5) 0.014(6) C5 0.047(5) 0.051(6) 0.052(6) -0.001(5) 0.007(5) -0.003(5) C6 0.048(5) 0.041(6) 0.046(6) -0.003(5) 0.005(4) -0.007(5) C7 0.045(4) 0.049(6) 0.065(6) -0.001(5) 0.001(5) 0.010(5) C8 0.053(5) 0.056(6) 0.057(6) 0.003(5) 0.012(5) 0.008(5) C9 0.047(5) 0.064(7) 0.057(6) 0.008(5) 0.016(4) 0.005(5) C10 0.043(4) 0.050(6) 0.048(6) 0.000(5) 0.006(5) -0.002(5) C11 0.045(5) 0.058(7) 0.067(6) 0.002(5) 0.003(5) -0.002(5) C12 0.041(4) 0.060(6) 0.057(6) 0.005(5) 0.007(4) 0.002(5) C13 0.107(7) 0.097(9) 0.066(6) -0.007(6) -0.013(6) -0.012(7) C14 0.050(6) 0.084(9) 0.046(6) 0.011(6) -0.008(4) -0.016(7) C15 0.061(6) 0.092(8) 0.052(7) -0.002(6) 0.001(5) 0.009(6) C16 0.061(6) 0.087(8) 0.077(8) -0.006(7) 0.020(6) -0.003(6) C17 0.085(7) 0.093(8) 0.053(6) -0.003(6) 0.009(6) 0.014(7) C18 0.073(6) 0.116(10) 0.067(8) -0.023(7) -0.010(6) 0.009(7) C19 0.048(5) 0.077(8) 0.082(8) -0.004(6) 0.010(5) 0.005(5) C20 0.052(5) 0.049(6) 0.057(6) -0.004(5) 0.008(5) 0.003(5) C21 0.071(6) 0.052(6) 0.068(6) -0.007(6) -0.001(5) -0.001(5) C22 0.085(6) 0.067(7) 0.056(6) 0.029(6) -0.012(6) -0.006(6) C23 0.059(6) 0.064(7) 0.050(6) 0.008(6) -0.008(5) 0.008(6) C24 0.072(6) 0.088(9) 0.058(7) 0.021(6) -0.004(6) -0.002(7) C25 0.107(9) 0.100(10) 0.068(8) 0.010(7) -0.003(7) -0.022(8) C26 0.105(8) 0.101(10) 0.061(7) 0.013(7) 0.025(7) 0.005(8) C27 0.062(6) 0.105(10) 0.078(8) 0.020(7) 0.014(6) 0.016(7) C28 0.056(6) 0.074(8) 0.077(8) 0.021(6) -0.008(5) -0.012(6) N1 0.045(4) 0.050(5) 0.069(5) 0.007(4) -0.003(4) -0.003(4) O1 0.079(4) 0.095(5) 0.054(4) 0.017(4) 0.009(4) 0.018(4) O2 0.048(3) 0.069(5) 0.086(5) 0.017(4) -0.002(3) -0.003(4) O3 0.046(3) 0.064(5) 0.098(5) 0.006(3) 0.015(3) 0.000(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.395(10) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C7 1.357(10) . ? C2 O1 1.370(9) . ? C2 C3 1.400(11) . ? C3 C4 1.350(10) . ? C3 H3 0.9300 . ? C4 C5 1.422(10) . ? C4 H4 0.9300 . ? C5 C11 1.405(10) . ? C5 C6 1.421(10) . ? C6 C8 1.400(9) . ? C6 C7 1.424(10) . ? C7 H7 0.9300 . ? C8 C9 1.356(10) . ? C8 H8 0.9300 . ? C9 C10 1.405(10) . ? C9 H9 0.9300 . ? C10 C11 1.376(10) . ? C10 C12 1.504(9) . ? C11 H11 0.9300 . ? C12 C13 1.533(11) . ? C12 C14 1.548(11) . ? C12 H12 0.9800 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 O2 1.254(10) . ? C14 O3 1.268(10) 1 ? C14 O3 1.268(10) . ? C15 C16 1.387(11) . ? C15 C20 1.391(10) . ? C15 H15 0.9300 . ? C16 C17 1.390(11) . ? C16 H16 0.9300 . ? C17 C18 1.373(12) . ? C17 H17 0.9300 . ? C18 C19 1.367(12) . ? C18 H18 0.9300 . ? C19 C20 1.391(10) . ? C19 H19 0.9300 . ? C20 C21 1.504(10) . ? C21 N1 1.496(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.472(11) . ? C22 N1 1.494(9) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.370(11) . ? C23 C28 1.399(11) . ? C24 C25 1.383(12) . ? C24 H24 0.9300 . ? C25 C26 1.353(12) . ? C25 H25 0.9300 . ? C26 C27 1.386(12) . ? C26 H26 0.9300 . ? C27 C28 1.357(11) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? N1 H1D 0.9000 . ? N1 H1E 0.9000 . ? O3 O3 0.000(19) 1 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 O1 125.6(8) . . ? C7 C2 C3 120.4(8) . . ? O1 C2 C3 114.0(8) . . ? C4 C3 C2 121.0(8) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 121.3(8) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C11 C5 C6 118.5(7) . . ? C11 C5 C4 123.9(8) . . ? C6 C5 C4 117.5(8) . . ? C8 C6 C5 118.3(8) . . ? C8 C6 C7 122.2(8) . . ? C5 C6 C7 119.5(7) . . ? C2 C7 C6 120.3(7) . . ? C2 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C6 121.0(7) . . ? C9 C8 H8 119.5 . . ? C6 C8 H8 119.5 . . ? C8 C9 C10 122.6(7) . . ? C8 C9 H9 118.7 . . ? C10 C9 H9 118.7 . . ? C11 C10 C9 116.6(7) . . ? C11 C10 C12 120.4(7) . . ? C9 C10 C12 123.0(7) . . ? C10 C11 C5 122.9(7) . . ? C10 C11 H11 118.5 . . ? C5 C11 H11 118.5 . . ? C10 C12 C13 111.3(7) . . ? C10 C12 C14 113.2(6) . . ? C13 C12 C14 111.2(7) . . ? C10 C12 H12 106.9 . . ? C13 C12 H12 106.9 . . ? C14 C12 H12 106.9 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 O3 123.8(8) . 1 ? O2 C14 O3 123.8(8) . . ? O3 C14 O3 0.0(7) 1 . ? O2 C14 C12 119.8(8) . . ? O3 C14 C12 116.4(10) 1 . ? O3 C14 C12 116.4(10) . . ? C16 C15 C20 121.4(8) . . ? C16 C15 H15 119.3 . . ? C20 C15 H15 119.3 . . ? C15 C16 C17 119.1(9) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C18 C17 C16 119.7(9) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C19 C18 C17 121.0(9) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C20 121.0(9) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C19 C20 C15 117.8(8) . . ? C19 C20 C21 121.6(8) . . ? C15 C20 C21 120.4(8) . . ? N1 C21 C20 113.7(7) . . ? N1 C21 H21A 108.8 . . ? C20 C21 H21A 108.8 . . ? N1 C21 H21B 108.8 . . ? C20 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C23 C22 N1 113.7(7) . . ? C23 C22 H22A 108.8 . . ? N1 C22 H22A 108.8 . . ? C23 C22 H22B 108.8 . . ? N1 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? C24 C23 C28 116.3(9) . . ? C24 C23 C22 121.5(8) . . ? C28 C23 C22 122.1(10) . . ? C23 C24 C25 121.5(9) . . ? C23 C24 H24 119.2 . . ? C25 C24 H24 119.2 . . ? C26 C25 C24 121.0(11) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 C27 118.8(10) . . ? C25 C26 H26 120.6 . . ? C27 C26 H26 120.6 . . ? C28 C27 C26 119.7(9) . . ? C28 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C27 C28 C23 122.5(10) . . ? C27 C28 H28 118.8 . . ? C23 C28 H28 118.8 . . ? C22 N1 C21 110.9(7) . . ? C22 N1 H1D 109.5 . . ? C21 N1 H1D 109.5 . . ? C22 N1 H1E 109.5 . . ? C21 N1 H1E 109.5 . . ? H1D N1 H1E 108.0 . . ? C2 O1 C1 118.4(7) . . ? O3 O3 C14 0(10) 1 . ? 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 H1D O2 0.90 1.78 2.682(8) 174.4 1_655 N1 H1E O3 0.90 1.84 2.739(8) 177.2 1 _diffrn_measured_fraction_theta_max 0.599 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.728 _refine_diff_density_max 0.251 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.087 # _vrf_PLAT029_jm0198j_0m ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.728. RESPONSE: The crystal was poorly diffracting at higher Bragg angles. The situation did not improve even after recrystallisation and fresh data collection. ; _vrf_PLAT340_jm0198j_0m ; PROBLM: Low Bond Precision on C-C Bonds ............... 0.0126 Ang. RESPONSE: The crystal was poorly diffracting at higher Bragg angles. The situation did not improve even after recrystallisation and fresh data collection. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 947072' ####################################################################### # # 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_jm117_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_absolute_configuration syn _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 N O4, C6 H14 N, H2 O' _chemical_formula_sum 'C23 H34 N2 O5' _chemical_formula_weight 418.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.3305(11) _cell_length_b 6.4425(8) _cell_length_c 19.573(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.120(3) _cell_angle_gamma 90.00 _cell_volume 1161.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9592 _exptl_absorpt_correction_T_max 0.9933 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II' _diffrn_measurement_method 'Phi-Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7339 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.05 _diffrn_reflns_theta_max 20.76 _reflns_number_total 2288 _reflns_number_gt 1984 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury 2.3' _computing_publication_material 'Shelxl 97' _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^)+(0.1000P)^2^+0.1739P] 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 2288 _refine_ls_number_parameters 286 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 0.816 _refine_ls_restrained_S_all 0.815 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0730(5) 1.0874(8) 0.3791(2) 0.0820(15) Uani 1 1 d . . . H1A H -0.1097 1.0914 0.4222 0.123 Uiso 1 1 calc R . . H1B H -0.1527 1.0828 0.3416 0.123 Uiso 1 1 calc R . . H1C H -0.0158 1.2093 0.3749 0.123 Uiso 1 1 calc R . . C2 C 0.1263(4) 0.8789(7) 0.4316(2) 0.0593(11) Uani 1 1 d . . . C3 C 0.2055(5) 0.6939(7) 0.4280(2) 0.0700(12) Uani 1 1 d . . . H3 H 0.1824 0.6059 0.3902 0.084 Uiso 1 1 calc R . . C4 C 0.3148(4) 0.6437(7) 0.4793(2) 0.0646(11) Uani 1 1 d . . . H4 H 0.3664 0.5216 0.4760 0.077 Uiso 1 1 calc R . . C5 C 0.3524(4) 0.7715(6) 0.53755(18) 0.0501(10) Uani 1 1 d . . . C6 C 0.2755(4) 0.9593(6) 0.53995(18) 0.0530(10) Uani 1 1 d . . . C7 C 0.1610(4) 1.0105(7) 0.4852(2) 0.0629(11) Uani 1 1 d . . . H7 H 0.1105 1.1345 0.4864 0.075 Uiso 1 1 calc R . . C8 C 0.3133(5) 1.0885(7) 0.5978(2) 0.0690(12) Uani 1 1 d . . . H8 H 0.2666 1.2154 0.5997 0.083 Uiso 1 1 calc R . . C9 C 0.4171(4) 1.0302(7) 0.6509(2) 0.0655(11) Uani 1 1 d . . . H9 H 0.4405 1.1187 0.6885 0.079 Uiso 1 1 calc R . . C10 C 0.4898(4) 0.8401(6) 0.6505(2) 0.0537(10) Uani 1 1 d . . . C11 C 0.4585(4) 0.7163(6) 0.59391(18) 0.0536(10) Uani 1 1 d . . . H11 H 0.5084 0.5919 0.5924 0.064 Uiso 1 1 calc R . . C12 C 0.5981(4) 0.7838(7) 0.71421(19) 0.0619(11) Uani 1 1 d . . . H12 H 0.6412 0.9128 0.7346 0.074 Uiso 1 1 calc R . . C13 C 0.7217(5) 0.6423(10) 0.6996(2) 0.0953(16) Uani 1 1 d . . . H13A H 0.6834 0.5081 0.6853 0.143 Uiso 1 1 calc R . . H13B H 0.7920 0.6283 0.7408 0.143 Uiso 1 1 calc R . . H13C H 0.7672 0.7018 0.6635 0.143 Uiso 1 1 calc R . . C14 C 0.5205(4) 0.6775(7) 0.76793(19) 0.0555(10) Uani 1 1 d . . . C15 C 0.4653(3) 0.7021(6) 0.88652(17) 0.0543(10) Uani 1 1 d . . . H15A H 0.4474 0.5541 0.8818 0.065 Uiso 1 1 calc R . . H15B H 0.3736 0.7705 0.8888 0.065 Uiso 1 1 calc R . . C16 C 0.5701(3) 0.7441(6) 0.95239(17) 0.0522(10) Uani 1 1 d . . . H16A H 0.5231 0.7098 0.9917 0.063 Uiso 1 1 calc R . . H16B H 0.5926 0.8911 0.9549 0.063 Uiso 1 1 calc R . . C17 C 0.7107(4) 0.6224(7) 0.95765(15) 0.0422(9) Uani 1 1 d . . . C18 C -0.0425(4) 0.1462(6) 0.87337(17) 0.0491(9) Uani 1 1 d . . . H18 H -0.1319 0.1444 0.8395 0.059 Uiso 1 1 calc R . . C19 C 0.0503(5) -0.0368(7) 0.8597(2) 0.0768(13) Uani 1 1 d . . . H19A H -0.0040 -0.1644 0.8617 0.092 Uiso 1 1 calc R . . H19B H 0.1358 -0.0431 0.8950 0.092 Uiso 1 1 calc R . . C20 C 0.0961(6) -0.0162(8) 0.7890(2) 0.0854(15) Uani 1 1 d . . . H20A H 0.1615 -0.1291 0.7826 0.102 Uiso 1 1 calc R . . H20B H 0.0110 -0.0286 0.7537 0.102 Uiso 1 1 calc R . . C21 C 0.1692(5) 0.1841(8) 0.7801(2) 0.0827(14) Uani 1 1 d . . . H21A H 0.1881 0.1945 0.7329 0.099 Uiso 1 1 calc R . . H21B H 0.2618 0.1875 0.8107 0.099 Uiso 1 1 calc R . . C22 C 0.0799(6) 0.3662(8) 0.7955(3) 0.0884(15) Uani 1 1 d . . . H22A H -0.0064 0.3748 0.7607 0.106 Uiso 1 1 calc R . . H22B H 0.1353 0.4927 0.7932 0.106 Uiso 1 1 calc R . . C23 C 0.0358(5) 0.3482(7) 0.8663(2) 0.0723(13) Uani 1 1 d . . . H23A H 0.1215 0.3555 0.9014 0.087 Uiso 1 1 calc R . . H23B H -0.0271 0.4634 0.8735 0.087 Uiso 1 1 calc R . . N1 N -0.0820(3) 0.1309(5) 0.94482(13) 0.0487(8) Uani 1 1 d . . . H1D H -0.0023 0.1445 0.9762 0.073 Uiso 1 1 calc R . . H1E H -0.1225 0.0079 0.9499 0.073 Uiso 1 1 calc R . . H1F H -0.1445 0.2312 0.9507 0.073 Uiso 1 1 calc R . . N2 N 0.5242(3) 0.7774(6) 0.82700(15) 0.0519(8) Uani 1 1 d . . . O1 O 0.0148(3) 0.9076(5) 0.37711(13) 0.0749(9) Uani 1 1 d . . . O2 O 0.4631(4) 0.5066(5) 0.75633(14) 0.0846(9) Uani 1 1 d . . . O3 O 0.7050(2) 0.4294(4) 0.95598(12) 0.0542(7) Uani 1 1 d . . . O4 O 0.8276(3) 0.7236(4) 0.96501(12) 0.0584(7) Uani 1 1 d . . . O5 O 0.5887(4) 0.2010(5) 0.8419(2) 0.1020(12) Uani 1 1 d . . . H25 H 0.565(3) 0.923(7) 0.8325(16) 0.049(10) Uiso 1 1 d . . . H26 H 0.545(5) 0.311(10) 0.803(3) 0.118(18) Uiso 1 1 d . . . H27 H 0.603(5) 0.275(8) 0.881(2) 0.085(16) 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 C1 0.066(3) 0.108(4) 0.072(3) 0.006(3) 0.013(2) 0.018(3) C2 0.054(2) 0.078(3) 0.049(2) 0.002(2) 0.014(2) -0.001(2) C3 0.081(3) 0.068(3) 0.063(3) -0.014(2) 0.016(2) 0.008(3) C4 0.066(3) 0.064(3) 0.065(3) -0.008(2) 0.016(2) 0.014(2) C5 0.054(2) 0.052(3) 0.048(2) -0.002(2) 0.0180(19) -0.004(2) C6 0.060(2) 0.051(3) 0.053(2) -0.001(2) 0.023(2) 0.005(2) C7 0.070(3) 0.063(3) 0.059(3) 0.000(2) 0.020(2) 0.010(2) C8 0.083(3) 0.057(3) 0.067(3) -0.010(2) 0.014(3) 0.018(2) C9 0.073(3) 0.070(3) 0.053(2) -0.010(2) 0.008(2) 0.006(3) C10 0.051(2) 0.055(3) 0.059(3) 0.004(2) 0.0211(19) 0.001(2) C11 0.054(2) 0.055(2) 0.055(2) -0.002(2) 0.019(2) 0.003(2) C12 0.060(2) 0.068(3) 0.060(2) 0.002(2) 0.015(2) 0.000(2) C13 0.066(3) 0.130(5) 0.090(3) 0.001(3) 0.013(2) 0.030(3) C14 0.060(2) 0.045(3) 0.059(3) 0.001(2) 0.0015(19) 0.005(2) C15 0.0421(19) 0.062(3) 0.059(2) 0.005(2) 0.0093(18) 0.008(2) C16 0.050(2) 0.054(2) 0.056(2) -0.0029(19) 0.0203(18) 0.0102(19) C17 0.044(2) 0.047(3) 0.036(2) -0.0040(18) 0.0082(16) 0.002(2) C18 0.0432(19) 0.054(2) 0.051(2) 0.0009(19) 0.0086(16) 0.003(2) C19 0.102(3) 0.049(3) 0.088(3) -0.007(2) 0.041(3) 0.004(2) C20 0.096(4) 0.083(4) 0.085(3) -0.018(3) 0.035(3) 0.013(3) C21 0.078(3) 0.097(4) 0.080(3) 0.010(3) 0.034(2) 0.007(3) C22 0.121(4) 0.067(3) 0.088(3) 0.016(3) 0.053(3) 0.008(3) C23 0.101(3) 0.049(3) 0.075(3) 0.005(2) 0.037(3) 0.003(2) N1 0.0408(16) 0.0435(18) 0.0625(19) -0.0019(15) 0.0104(14) -0.0003(15) N2 0.0517(19) 0.051(2) 0.051(2) -0.0003(17) 0.0041(15) -0.0007(17) O1 0.0670(18) 0.098(2) 0.0590(18) -0.0030(16) 0.0059(15) 0.0119(18) O2 0.122(2) 0.060(2) 0.0706(19) -0.0077(16) 0.0118(16) -0.029(2) O3 0.0434(15) 0.0426(19) 0.0771(18) -0.0023(14) 0.0106(12) 0.0021(13) O4 0.0444(14) 0.0538(17) 0.0744(17) 0.0067(13) 0.0018(12) -0.0051(14) O5 0.115(3) 0.052(2) 0.121(3) -0.017(2) -0.034(2) 0.0074(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.423(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C7 1.347(6) . ? C2 O1 1.380(4) . ? C2 C3 1.410(6) . ? C3 C4 1.353(5) . ? C3 H3 0.9300 . ? C4 C5 1.405(5) . ? C4 H4 0.9300 . ? C5 C11 1.406(5) . ? C5 C6 1.411(5) . ? C6 C8 1.404(5) . ? C6 C7 1.427(5) . ? C7 H7 0.9300 . ? C8 C9 1.356(5) . ? C8 H8 0.9300 . ? C9 C10 1.400(6) . ? C9 H9 0.9300 . ? C10 C11 1.359(5) . ? C10 C12 1.519(5) . ? C11 H11 0.9300 . ? C12 C14 1.530(5) . ? C12 C13 1.532(6) . ? C12 H12 0.9800 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 O2 1.229(5) 1 ? C14 O2 1.229(5) . ? C14 N2 1.319(5) . ? C15 N2 1.448(4) . ? C15 C16 1.514(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.518(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O3 1.244(4) . ? C17 O4 1.260(4) . ? C18 N1 1.505(4) . ? C18 C23 1.510(6) . ? C18 C19 1.512(5) . ? C18 H18 0.9800 . ? C19 C20 1.516(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.483(7) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.496(7) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.512(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? N1 H1D 0.8900 . ? N1 H1E 0.8900 . ? N1 H1F 0.8900 . ? N2 H25 1.01(4) . ? O2 O2 0.000(9) 1 ? O5 H26 1.07(6) . ? O5 H27 0.89(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 O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 O1 125.2(4) . . ? C7 C2 C3 120.5(4) . . ? O1 C2 C3 114.3(4) . . ? C4 C3 C2 120.3(4) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 121.6(4) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C4 C5 C11 122.8(4) . . ? C4 C5 C6 117.8(3) . . ? C11 C5 C6 119.3(3) . . ? C8 C6 C5 118.1(3) . . ? C8 C6 C7 122.1(4) . . ? C5 C6 C7 119.8(3) . . ? C2 C7 C6 119.9(4) . . ? C2 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C6 120.7(4) . . ? C9 C8 H8 119.6 . . ? C6 C8 H8 119.6 . . ? C8 C9 C10 121.7(4) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C11 C10 C9 118.4(4) . . ? C11 C10 C12 123.9(4) . . ? C9 C10 C12 117.7(4) . . ? C10 C11 C5 121.7(4) . . ? C10 C11 H11 119.2 . . ? C5 C11 H11 119.2 . . ? C10 C12 C14 110.2(3) . . ? C10 C12 C13 114.3(3) . . ? C14 C12 C13 108.3(4) . . ? C10 C12 H12 108.0 . . ? C14 C12 H12 108.0 . . ? C13 C12 H12 108.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 O2 0.0(3) 1 . ? O2 C14 N2 123.3(4) 1 . ? O2 C14 N2 123.3(4) . . ? O2 C14 C12 120.9(4) 1 . ? O2 C14 C12 120.9(4) . . ? N2 C14 C12 115.8(4) . . ? N2 C15 C16 110.4(3) . . ? N2 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? N2 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C17 113.6(3) . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16B 108.9 . . ? C17 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? O3 C17 O4 123.6(3) . . ? O3 C17 C16 118.8(3) . . ? O4 C17 C16 117.6(4) . . ? N1 C18 C23 109.6(3) . . ? N1 C18 C19 110.2(3) . . ? C23 C18 C19 110.9(3) . . ? N1 C18 H18 108.7 . . ? C23 C18 H18 108.7 . . ? C19 C18 H18 108.7 . . ? C18 C19 C20 110.2(4) . . ? C18 C19 H19A 109.6 . . ? C20 C19 H19A 109.6 . . ? C18 C19 H19B 109.6 . . ? C20 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? C21 C20 C19 112.6(4) . . ? C21 C20 H20A 109.1 . . ? C19 C20 H20A 109.1 . . ? C21 C20 H20B 109.1 . . ? C19 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? C20 C21 C22 112.2(4) . . ? C20 C21 H21A 109.2 . . ? C22 C21 H21A 109.2 . . ? C20 C21 H21B 109.2 . . ? C22 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? C21 C22 C23 111.4(4) . . ? C21 C22 H22A 109.3 . . ? C23 C22 H22A 109.3 . . ? C21 C22 H22B 109.3 . . ? C23 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? C18 C23 C22 110.9(4) . . ? C18 C23 H23A 109.5 . . ? C22 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C18 N1 H1D 109.5 . . ? C18 N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? C18 N1 H1F 109.5 . . ? H1D N1 H1F 109.5 . . ? H1E N1 H1F 109.5 . . ? C14 N2 C15 125.5(4) . . ? C14 N2 H25 120.1(18) . . ? C15 N2 H25 114.3(18) . . ? C2 O1 C1 117.0(3) . . ? O2 O2 C14 0(10) 1 . ? H26 O5 H27 104(5) . . ? 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 O5 H26 O2 1.07(6) 1.67(7) 2.726(5) 167(5) 1 N2 H25 O5 1.01(4) 1.81(4) 2.800(5) 165(3) 1_565 N1 H1F O3 0.89 1.91 2.799(4) 173.4 1_455 N1 H1E O4 0.89 1.92 2.803(4) 169.0 1_445 N1 H1D O4 0.89 1.91 2.789(3) 169.0 2_647 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 20.76 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.115 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.029 # _vrf_THETM01_jm117_0m ; PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550 Calculated sin(theta_max)/wavelength = 0.4987. RESPONSE: The crystal was poorly diffracting at higher Bragg angles. The situation did not improve even after recrystallisation and fresh data collection. ; _vrf_PLAT089_jm117_0m ; PROBLM: Poor Data / Parameter Ratio (Zmax < 18) ..... 4.74 RESPONSE: The crystal was poorly diffracting at higher Bragg angles. The situation did not improve even after recrystallisation and fresh data collection. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 947177' ####################################################################### # # 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_jm01102r _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_absolute_configuration syn _chemical_melting_point ? _chemical_formula_moiety '2(C16 H16 N O2), C14 H16 N, 1.02(O2), 2(C), 1.96(O)' _chemical_formula_sum 'C48 H48 N3 O8' _chemical_formula_weight 794.89 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 C2 _symmetry_space_group_name_Hall C2Y 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 23.570(4) _cell_length_b 4.8479(8) _cell_length_c 18.554(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.115(9) _cell_angle_gamma 90.00 _cell_volume 2120.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 842 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9305 _exptl_absorpt_correction_T_max 0.9850 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II' _diffrn_measurement_method 'Phi-Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14773 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_max 28.20 _reflns_number_total 4381 _reflns_number_gt 2624 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 2.3' _computing_publication_material 'Shelxl 97' _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^)+(0.1000P)^2^+0.3072P] 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 4381 _refine_ls_number_parameters 277 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1171 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.2047 _refine_ls_wR_factor_gt 0.1533 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.144 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4258(3) 1.0629(17) 0.5228(3) 0.118(2) Uani 1 1 d . . . H1A H 0.4409 0.8843 0.5343 0.177 Uiso 1 1 calc R . . H1B H 0.3882 1.0793 0.5421 0.177 Uiso 1 1 calc R . . H1C H 0.4497 1.2030 0.5433 0.177 Uiso 1 1 calc R . . C2 C 0.37505(16) 1.0214(9) 0.3375(2) 0.0588(10) Uani 1 1 d . . . H2 H 0.3981 1.1564 0.3174 0.071 Uiso 1 1 calc R . . C3 C 0.33460(15) 0.8958(9) 0.29635(19) 0.0520(10) Uani 1 1 d . . . H3 H 0.3305 0.9463 0.2483 0.062 Uiso 1 1 calc R . . C4 C 0.29873(14) 0.6906(8) 0.32539(17) 0.0437(8) Uani 1 1 d . . . C5 C 0.30702(14) 0.6145(8) 0.39827(17) 0.0436(8) Uani 1 1 d . . . C6 C 0.34944(16) 0.7473(9) 0.43973(18) 0.0520(9) Uani 1 1 d . . . H6 H 0.3550 0.6965 0.4876 0.062 Uiso 1 1 calc R . . C7 C 0.38203(15) 0.9475(10) 0.4104(2) 0.0560(10) Uani 1 1 d . . . C8 C 0.25561(15) 0.5598(8) 0.28459(17) 0.0447(8) Uani 1 1 d . . . H8 H 0.2501 0.6113 0.2368 0.054 Uiso 1 1 calc R . . C9 C 0.22200(15) 0.3601(7) 0.31370(16) 0.0444(8) Uani 1 1 d . . . C10 C 0.23137(16) 0.2829(8) 0.38624(18) 0.0521(9) Uani 1 1 d . . . H10 H 0.2092 0.1444 0.4064 0.063 Uiso 1 1 calc R . . C11 C 0.27185(16) 0.4058(8) 0.42709(18) 0.0509(9) Uani 1 1 d . . . H11 H 0.2766 0.3519 0.4748 0.061 Uiso 1 1 calc R . . C12 C 0.17636(15) 0.2112(8) 0.27253(19) 0.0528(9) Uani 1 1 d . . . H12 H 0.1782 0.0158 0.2858 0.063 Uiso 1 1 calc R . . C13 C 0.1814(2) 0.2303(14) 0.1899(2) 0.0880(17) Uani 1 1 d . . . H13A H 0.2178 0.1621 0.1752 0.132 Uiso 1 1 calc R . . H13B H 0.1775 0.4192 0.1751 0.132 Uiso 1 1 calc R . . H13C H 0.1521 0.1216 0.1679 0.132 Uiso 1 1 calc R . . C14 C 0.11736(16) 0.3187(8) 0.29313(19) 0.0480(9) Uani 1 1 d . . . C15 C 0.01759(17) 0.1919(9) 0.3064(2) 0.0479(9) Uani 1 1 d . . . C16A C -0.0103(3) 0.2250(18) 0.2305(4) 0.0541(17) Uiso 0.52 1 d P . . C16B C -0.0125(3) 0.0372(16) 0.2492(3) 0.0422(16) Uiso 0.48 1 d P . . C17B C -0.0019(3) -0.0233(17) 0.1873(3) 0.0466(16) Uiso 0.54 1 d P . . C17A C 0.0095(3) 0.0914(18) 0.1723(4) 0.0406(17) Uiso 0.46 1 d P . . C18 C 0.19133(18) 1.0031(12) 0.9318(3) 0.0785(14) Uani 1 1 d . . . H18 H 0.2215 1.1159 0.9188 0.094 Uiso 1 1 calc R . . C19 C 0.16025(18) 0.8692(11) 0.8803(2) 0.0724(13) Uani 1 1 d . . . H19 H 0.1690 0.8944 0.8319 0.087 Uiso 1 1 calc R . . C20 C 0.11657(18) 0.6994(10) 0.8988(2) 0.0620(11) Uani 1 1 d . . . H20 H 0.0961 0.6092 0.8629 0.074 Uiso 1 1 calc R . . C21 C 0.10215(15) 0.6591(8) 0.97065(19) 0.0502(9) Uani 1 1 d . . . C22 C 0.13354(19) 0.7957(12) 1.0218(2) 0.0710(12) Uani 1 1 d . . . H22 H 0.1251 0.7713 1.0703 0.085 Uiso 1 1 calc R . . C23 C 0.1777(2) 0.9695(13) 1.0022(3) 0.0829(15) Uani 1 1 d . . . H23 H 0.1979 1.0635 1.0375 0.099 Uiso 1 1 calc R . . C24 C 0.05279(17) 0.4781(9) 0.9905(2) 0.0600(11) Uani 1 1 d . . . H24A H 0.0468 0.3421 0.9529 0.072 Uiso 1 1 calc R . . H24B H 0.0613 0.3809 1.0349 0.072 Uiso 1 1 calc R . . N1 N 0.0000 0.6459(9) 1.0000 0.0447(9) Uani 1 2 d S . . H1D H 0.0044 0.7555 1.0388 0.054 Uiso 0.50 1 calc PR . . H1E H -0.0044 0.7555 0.9612 0.054 Uiso 0.50 1 calc PR . . N2 N 0.07748(14) 0.1307(7) 0.30363(17) 0.0456(8) Uani 1 1 d . . . O1 O 0.42385(12) 1.0958(8) 0.44635(16) 0.0810(10) Uani 1 1 d . . . O2 O 0.10777(13) 0.5662(6) 0.29587(19) 0.0790(10) Uani 1 1 d . . . O3A O 0.0147(2) 0.3342(13) 0.1509(3) 0.0622(14) Uiso 0.49 1 d P . . O3B O 0.0102(3) -0.0230(14) 0.1212(3) 0.0532(16) Uiso 0.51 1 d P . . O4A O 0.0222(3) -0.1072(15) 0.1344(3) 0.0621(18) Uiso 0.51 1 d P . . O4B O -0.0118(2) -0.2596(11) 0.2199(3) 0.0516(12) Uiso 0.49 1 d P . . H1 H 0.0843(18) -0.006(11) 0.300(2) 0.057(14) Uiso 1 1 d . . . H3A H 0.0027(16) 0.110(9) 0.340(2) 0.054(12) Uiso 1 1 d . . . H2A H 0.0128(17) 0.381(11) 0.321(2) 0.063(12) 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 C1 0.125(5) 0.153(7) 0.075(3) 0.006(4) -0.030(3) -0.051(5) C2 0.048(2) 0.059(3) 0.070(2) 0.006(2) 0.0169(18) -0.004(2) C3 0.050(2) 0.057(3) 0.0488(18) 0.0092(17) 0.0097(16) 0.0059(19) C4 0.0409(18) 0.044(2) 0.0463(17) 0.0039(16) 0.0094(14) 0.0084(16) C5 0.0431(18) 0.045(2) 0.0429(17) -0.0001(14) 0.0074(14) 0.0075(17) C6 0.052(2) 0.060(3) 0.0441(17) 0.0051(17) 0.0033(15) 0.0017(19) C7 0.044(2) 0.063(3) 0.061(2) -0.006(2) 0.0041(16) 0.001(2) C8 0.051(2) 0.0401(19) 0.0425(17) 0.0021(14) 0.0063(14) 0.0092(17) C9 0.048(2) 0.039(2) 0.0456(18) -0.0067(15) 0.0070(15) 0.0070(16) C10 0.061(2) 0.045(2) 0.0511(19) 0.0012(17) 0.0174(17) 0.001(2) C11 0.062(2) 0.050(2) 0.0404(16) 0.0043(16) 0.0076(16) 0.001(2) C12 0.057(2) 0.039(2) 0.062(2) -0.0090(17) 0.0013(17) 0.0084(18) C13 0.079(3) 0.123(5) 0.062(2) -0.030(3) 0.004(2) -0.017(3) C14 0.057(2) 0.0273(19) 0.059(2) -0.0014(15) -0.0022(16) 0.0051(17) C15 0.056(2) 0.041(2) 0.0470(19) -0.0034(17) 0.0034(17) 0.0021(18) C18 0.060(3) 0.086(4) 0.089(3) -0.019(3) 0.018(2) -0.018(3) C19 0.074(3) 0.078(3) 0.065(2) -0.003(2) 0.021(2) -0.010(3) C20 0.065(2) 0.068(3) 0.053(2) -0.009(2) 0.0127(17) -0.009(2) C21 0.055(2) 0.044(2) 0.0523(19) -0.0055(17) 0.0104(16) 0.0092(19) C22 0.072(3) 0.086(3) 0.055(2) -0.006(2) 0.0022(19) 0.011(3) C23 0.065(3) 0.102(4) 0.081(3) -0.031(3) -0.002(2) -0.006(3) C24 0.075(3) 0.042(2) 0.063(2) 0.0022(18) 0.0229(19) 0.011(2) N1 0.055(2) 0.038(2) 0.0410(19) 0.000 0.0077(17) 0.000 N2 0.0548(19) 0.0256(16) 0.0563(18) -0.0010(14) -0.0022(13) 0.0055(15) O1 0.0611(17) 0.100(3) 0.0825(19) -0.0015(18) -0.0076(14) -0.0231(19) O2 0.0688(18) 0.0237(15) 0.145(3) -0.0034(16) -0.0034(18) 0.0082(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 C1 O1 1.427(6) . ? C2 C3 1.364(5) . ? C2 C7 1.407(5) . ? C3 C4 1.413(5) . ? C4 C5 1.415(4) . ? C4 C8 1.416(5) . ? C5 C11 1.413(5) . ? C5 C6 1.415(5) . ? C6 C7 1.353(6) . ? C7 O1 1.390(5) . ? C8 C9 1.363(5) . ? C9 C10 1.414(5) . ? C9 C12 1.503(5) . ? C10 C11 1.355(5) . ? C12 C14 1.534(5) . ? C12 C13 1.541(5) . ? C14 O2 1.222(5) . ? C14 N2 1.324(5) . ? C15 N2 1.444(5) . ? C15 C16B 1.479(8) . ? C15 C16A 1.560(8) . ? C16A C16B 0.976(10) . ? C16A C17A 1.343(10) . ? C16A C17B 1.459(11) . ? C16A O3A 1.676(9) . ? C16B C17B 1.212(9) . ? C16B O4B 1.539(10) . ? C16B C17A 1.542(10) . ? C17B C17A 0.678(9) . ? C17B O4A 1.205(9) . ? C17B O3B 1.261(8) . ? C17B O4B 1.316(10) . ? C17B O3A 1.901(11) . ? C17A O3B 1.100(8) . ? C17A O4A 1.229(10) . ? C17A O3A 1.248(11) . ? C18 C23 1.355(6) . ? C18 C19 1.368(6) . ? C19 C20 1.363(6) . ? C20 C21 1.390(5) . ? C21 C22 1.372(6) . ? C21 C24 1.503(6) . ? C22 C23 1.388(7) . ? C24 N1 1.497(4) . ? N1 C24 1.497(4) 2_557 ? O3B O4A 0.553(8) . ? 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 C3 C2 C7 120.3(4) . . ? C2 C3 C4 121.2(3) . . ? C3 C4 C5 117.8(3) . . ? C3 C4 C8 122.7(3) . . ? C5 C4 C8 119.4(3) . . ? C11 C5 C4 117.9(3) . . ? C11 C5 C6 122.3(3) . . ? C4 C5 C6 119.8(3) . . ? C7 C6 C5 120.6(3) . . ? C6 C7 O1 125.5(4) . . ? C6 C7 C2 120.3(4) . . ? O1 C7 C2 114.3(4) . . ? C9 C8 C4 121.6(3) . . ? C8 C9 C10 118.4(3) . . ? C8 C9 C12 123.8(3) . . ? C10 C9 C12 117.8(3) . . ? C11 C10 C9 121.6(3) . . ? C10 C11 C5 121.0(3) . . ? C9 C12 C14 111.0(3) . . ? C9 C12 C13 114.8(3) . . ? C14 C12 C13 107.4(3) . . ? O2 C14 N2 122.6(4) . . ? O2 C14 C12 120.8(4) . . ? N2 C14 C12 116.6(3) . . ? N2 C15 C16B 109.8(4) . . ? N2 C15 C16A 113.5(4) . . ? C16B C15 C16A 37.3(4) . . ? C16B C16A C17A 81.7(8) . . ? C16B C16A C17B 55.5(6) . . ? C17A C16A C17B 27.6(4) . . ? C16B C16A C15 66.8(6) . . ? C17A C16A C15 122.0(6) . . ? C17B C16A C15 110.7(6) . . ? C16B C16A O3A 128.9(8) . . ? C17A C16A O3A 47.3(5) . . ? C17B C16A O3A 74.3(5) . . ? C15 C16A O3A 132.8(6) . . ? C16A C16B C17B 83.0(8) . . ? C16A C16B C15 75.8(7) . . ? C17B C16B C15 134.6(7) . . ? C16A C16B O4B 138.3(7) . . ? C17B C16B O4B 55.7(5) . . ? C15 C16B O4B 136.2(6) . . ? C16A C16B C17A 59.5(7) . . ? C17B C16B C17A 25.0(4) . . ? C15 C16B C17A 114.5(6) . . ? O4B C16B C17A 80.1(5) . . ? C17A C17B O4A 75.8(10) . . ? C17A C17B C16B 105.9(11) . . ? O4A C17B C16B 162.1(8) . . ? C17A C17B O3B 60.6(9) . . ? O4A C17B O3B 25.8(4) . . ? C16B C17B O3B 165.9(9) . . ? C17A C17B O4B 166.7(12) . . ? O4A C17B O4B 99.4(7) . . ? C16B C17B O4B 74.9(6) . . ? O3B C17B O4B 119.2(7) . . ? C17A C17B C16A 66.6(10) . . ? O4A C17B C16A 142.1(8) . . ? C16B C17B C16A 41.6(5) . . ? O3B C17B C16A 124.4(8) . . ? O4B C17B C16A 116.2(6) . . ? C17A C17B O3A 12.6(8) . . ? O4A C17B O3A 85.5(6) . . ? C16B C17B O3A 99.1(6) . . ? O3B C17B O3A 66.8(5) . . ? O4B C17B O3A 173.4(5) . . ? C16A C17B O3A 58.1(4) . . ? C17B C17A O3B 87.0(11) . . ? C17B C17A O4A 71.9(10) . . ? O3B C17A O4A 26.8(4) . . ? C17B C17A O3A 160.5(13) . . ? O3B C17A O3A 101.5(7) . . ? O4A C17A O3A 122.2(7) . . ? C17B C17A C16A 85.8(10) . . ? O3B C17A C16A 160.5(8) . . ? O4A C17A C16A 157.3(9) . . ? O3A C17A C16A 80.5(6) . . ? C17B C17A C16B 49.1(9) . . ? O3B C17A C16B 135.9(9) . . ? O4A C17A C16B 118.6(8) . . ? O3A C17A C16B 119.2(7) . . ? C16A C17A C16B 38.8(4) . . ? C23 C18 C19 119.3(4) . . ? C20 C19 C18 120.9(4) . . ? C19 C20 C21 120.8(4) . . ? C22 C21 C20 117.6(4) . . ? C22 C21 C24 121.9(4) . . ? C20 C21 C24 120.5(3) . . ? C21 C22 C23 121.0(4) . . ? C18 C23 C22 120.3(4) . . ? N1 C24 C21 110.8(3) . . ? C24 N1 C24 114.2(4) 2_557 . ? C14 N2 C15 123.9(4) . . ? C7 O1 C1 116.2(4) . . ? C17A O3A C16A 52.2(5) . . ? C17A O3A C17B 6.8(4) . . ? C16A O3A C17B 47.7(4) . . ? O4A O3B C17A 89.8(11) . . ? O4A O3B C17B 71.5(11) . . ? C17A O3B C17B 32.5(5) . . ? O3B O4A C17B 82.7(12) . . ? O3B O4A C17A 63.4(11) . . ? C17B O4A C17A 32.3(4) . . ? C17B O4B C16B 49.5(4) . . ? 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 N2 H1 O2 0.68(5) 2.15(5) 2.832(4) 176(5) 1_545 N1 H1E O4A 0.90 1.94 2.814(6) 163.3 2_566 N1 H1E O3B 0.90 1.87 2.772(6) 177.2 2_566 N1 H1D O4A 0.90 1.94 2.814(6) 163.3 1_566 N1 H1D O3B 0.90 1.87 2.772(6) 177.2 1_566 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 28.20 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.270 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.084 # _vrf_PLAT201_jm01102r ; PROBLM: Isotropic non-H Atoms in Main Residue(s) ....... 1 RESPONSE: The non-hydrogen atoms C16, C17, O3 and O4 were refined with isotropic displacement parameters only in the main residue because of minor disorder modelling. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 955413'