# Electronic Supplementary Material (ESI) for Green 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 N2 O3' _chemical_formula_weight 330.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0629(11) _cell_length_b 11.2174(14) _cell_length_c 16.215(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.8350(10) _cell_angle_gamma 90.00 _cell_volume 1593.5(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 0.09 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.992 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10656 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 24.66 _reflns_number_total 2687 _reflns_number_gt 2238 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0874P)^2^+0.4205P] 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 0.0075(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2687 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 0.843 _refine_ls_restrained_S_all 0.843 _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 0.28084(13) 0.35602(9) 0.04623(7) 0.0568(3) Uani 1 1 d . . . O2 O 0.20885(16) 0.30727(10) 0.16144(8) 0.0703(4) Uani 1 1 d . . . O3 O 0.11964(13) 0.52781(9) 0.18626(7) 0.0564(3) Uani 1 1 d . . . N1 N -0.00210(19) 0.63697(15) 0.26199(10) 0.0645(4) Uani 1 1 d . . . H26 H -0.059(3) 0.698(2) 0.2717(15) 0.097 Uiso 1 1 d . . . H25 H 0.011(3) 0.571(2) 0.2954(15) 0.097 Uiso 1 1 d . . . N2 N -0.1069(2) 0.91072(14) 0.14283(10) 0.0774(5) Uani 1 1 d . . . C1 C 0.3531(2) 0.46940(18) -0.14743(12) 0.0727(5) Uani 1 1 d . . . H1 H 0.3933 0.4423 -0.1914 0.087 Uiso 1 1 calc R . . C2 C 0.2991(2) 0.58468(18) -0.14938(12) 0.0692(5) Uani 1 1 d . . . H2 H 0.3019 0.6343 -0.1949 0.083 Uiso 1 1 calc R . . C3 C 0.24120(19) 0.62643(15) -0.08440(10) 0.0581(4) Uani 1 1 d . . . H3 H 0.2061 0.7045 -0.0859 0.070 Uiso 1 1 calc R . . C4 C 0.23462(16) 0.55233(13) -0.01597(9) 0.0472(4) Uani 1 1 d . . . C5 C 0.17566(16) 0.58888(12) 0.05510(9) 0.0444(4) Uani 1 1 d . . . C6 C 0.11625(17) 0.71346(12) 0.06032(9) 0.0451(4) Uani 1 1 d . . . H6 H 0.0417 0.7310 0.0062 0.054 Uiso 1 1 calc R . . C7 C 0.23885(16) 0.80972(12) 0.07555(9) 0.0439(4) Uani 1 1 d . . . C8 C 0.2107(2) 0.91689(14) 0.03316(12) 0.0614(5) Uani 1 1 d . . . H8 H 0.1210 0.9269 -0.0096 0.074 Uiso 1 1 calc R . . C9 C 0.3133(2) 1.00962(15) 0.05313(13) 0.0685(5) Uani 1 1 d . . . H9 H 0.2906 1.0816 0.0242 0.082 Uiso 1 1 calc R . . C10 C 0.44847(18) 0.99831(14) 0.11483(11) 0.0550(4) Uani 1 1 d . . . C11 C 0.5578(2) 1.10110(17) 0.13626(16) 0.0798(6) Uani 1 1 d . . . H11A H 0.5681 1.1379 0.0846 0.120 Uiso 1 1 calc R . . H11B H 0.6556 1.0727 0.1683 0.120 Uiso 1 1 calc R . . H11C H 0.5197 1.1585 0.1696 0.120 Uiso 1 1 calc R . . C12 C 0.3483(2) 0.39450(16) -0.08153(12) 0.0644(5) Uani 1 1 d . . . H12 H 0.3845 0.3168 -0.0803 0.077 Uiso 1 1 calc R . . C13 C 0.28844(17) 0.43675(13) -0.01697(10) 0.0506(4) Uani 1 1 d . . . C14 C 0.22012(18) 0.38458(13) 0.11199(10) 0.0513(4) Uani 1 1 d . . . C15 C 0.17195(16) 0.50790(13) 0.11504(10) 0.0467(4) Uani 1 1 d . . . C16 C 0.04737(17) 0.63289(13) 0.19103(10) 0.0484(4) Uani 1 1 d . . . C17 C 0.03421(17) 0.71756(13) 0.13080(10) 0.0475(4) Uani 1 1 d . . . C18 C 0.47818(18) 0.89002(15) 0.15583(11) 0.0563(4) Uani 1 1 d . . . H18 H 0.5699 0.8791 0.1969 0.068 Uiso 1 1 calc R . . C19 C 0.37490(17) 0.79743(13) 0.13731(10) 0.0504(4) Uani 1 1 d . . . H19 H 0.3971 0.7258 0.1667 0.061 Uiso 1 1 calc R . . C20 C -0.04383(19) 0.82344(14) 0.13889(10) 0.0546(4) 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 O1 0.0686(7) 0.0428(6) 0.0657(7) -0.0057(5) 0.0297(6) -0.0003(5) O2 0.0983(9) 0.0450(6) 0.0777(8) 0.0077(6) 0.0409(7) 0.0043(6) O3 0.0758(8) 0.0464(6) 0.0546(7) 0.0029(5) 0.0308(6) 0.0085(5) N1 0.0835(10) 0.0598(9) 0.0600(9) 0.0010(7) 0.0360(8) 0.0113(8) N2 0.1070(13) 0.0631(9) 0.0682(10) 0.0027(7) 0.0336(9) 0.0285(9) C1 0.0833(13) 0.0782(13) 0.0690(12) -0.0182(10) 0.0422(10) -0.0120(10) C2 0.0845(13) 0.0724(12) 0.0588(11) -0.0039(9) 0.0333(9) -0.0146(10) C3 0.0687(10) 0.0551(9) 0.0553(10) -0.0039(7) 0.0242(8) -0.0085(8) C4 0.0474(8) 0.0462(8) 0.0499(9) -0.0088(6) 0.0157(7) -0.0108(6) C5 0.0444(8) 0.0413(8) 0.0483(8) -0.0061(6) 0.0133(6) -0.0061(6) C6 0.0474(8) 0.0434(8) 0.0441(8) -0.0004(6) 0.0108(6) -0.0014(6) C7 0.0477(8) 0.0416(7) 0.0443(8) -0.0022(6) 0.0153(6) -0.0002(6) C8 0.0617(10) 0.0491(9) 0.0647(10) 0.0091(7) 0.0000(8) -0.0042(7) C9 0.0763(12) 0.0454(9) 0.0788(12) 0.0108(8) 0.0107(10) -0.0084(8) C10 0.0561(9) 0.0496(9) 0.0625(10) -0.0093(7) 0.0211(8) -0.0064(7) C11 0.0755(13) 0.0625(11) 0.1024(15) -0.0171(10) 0.0244(11) -0.0200(9) C12 0.0691(11) 0.0586(10) 0.0751(12) -0.0168(9) 0.0358(9) -0.0060(8) C13 0.0514(9) 0.0477(8) 0.0564(9) -0.0078(7) 0.0204(7) -0.0097(7) C14 0.0576(9) 0.0432(8) 0.0566(9) -0.0041(7) 0.0211(7) -0.0041(7) C15 0.0498(8) 0.0440(8) 0.0486(8) -0.0041(6) 0.0170(7) -0.0032(6) C16 0.0492(8) 0.0461(8) 0.0520(9) -0.0055(7) 0.0168(7) -0.0008(6) C17 0.0470(8) 0.0441(8) 0.0534(9) -0.0042(6) 0.0163(7) -0.0007(6) C18 0.0481(9) 0.0609(10) 0.0574(10) -0.0080(7) 0.0088(7) -0.0007(7) C19 0.0533(9) 0.0451(8) 0.0522(9) 0.0034(6) 0.0124(7) 0.0022(7) C20 0.0627(10) 0.0520(9) 0.0513(9) -0.0016(7) 0.0185(8) 0.0043(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C14 1.3576(19) . ? O1 C13 1.3823(19) . ? O2 C14 1.2032(19) . ? O3 C16 1.3603(18) . ? O3 C15 1.3742(18) . ? N1 C16 1.338(2) . ? N1 H26 0.90(3) . ? N1 H25 0.90(3) . ? N2 C20 1.144(2) . ? C1 C12 1.369(3) . ? C1 C2 1.380(3) . ? C1 H1 0.9300 . ? C2 C3 1.374(2) . ? C2 H2 0.9300 . ? C3 C4 1.400(2) . ? C3 H3 0.9300 . ? C4 C13 1.387(2) . ? C4 C5 1.448(2) . ? C5 C15 1.337(2) . ? C5 C6 1.508(2) . ? C6 C17 1.515(2) . ? C6 C7 1.524(2) . ? C6 H6 0.9800 . ? C7 C8 1.376(2) . ? C7 C19 1.382(2) . ? C8 C9 1.378(2) . ? C8 H8 0.9300 . ? C9 C10 1.375(3) . ? C9 H9 0.9300 . ? C10 C18 1.378(2) . ? C10 C11 1.502(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.380(2) . ? C12 H12 0.9300 . ? C14 C15 1.455(2) . ? C16 C17 1.346(2) . ? C17 C20 1.406(2) . ? C18 C19 1.379(2) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O1 C13 122.33(12) . . ? C16 O3 C15 117.60(12) . . ? C16 N1 H26 120.8(15) . . ? C16 N1 H25 117.6(15) . . ? H26 N1 H25 121(2) . . ? C12 C1 C2 120.71(16) . . ? C12 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C3 C2 C1 120.31(17) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.51(16) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C13 C4 C3 117.34(14) . . ? C13 C4 C5 118.46(14) . . ? C3 C4 C5 124.19(14) . . ? C15 C5 C4 117.98(13) . . ? C15 C5 C6 120.86(13) . . ? C4 C5 C6 121.13(13) . . ? C5 C6 C17 108.77(12) . . ? C5 C6 C7 114.20(12) . . ? C17 C6 C7 109.54(11) . . ? C5 C6 H6 108.0 . . ? C17 C6 H6 108.0 . . ? C7 C6 H6 108.0 . . ? C8 C7 C19 117.79(14) . . ? C8 C7 C6 120.26(14) . . ? C19 C7 C6 121.68(13) . . ? C7 C8 C9 120.97(16) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C8 121.57(16) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C9 C10 C18 117.40(15) . . ? C9 C10 C11 120.64(16) . . ? C18 C10 C11 121.96(17) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 C12 C13 118.61(17) . . ? C1 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C12 C13 O1 116.18(14) . . ? C12 C13 C4 122.51(15) . . ? O1 C13 C4 121.29(13) . . ? O2 C14 O1 118.30(14) . . ? O2 C14 C15 125.81(15) . . ? O1 C14 C15 115.88(13) . . ? C5 C15 O3 125.36(13) . . ? C5 C15 C14 123.88(14) . . ? O3 C15 C14 110.74(13) . . ? N1 C16 C17 127.80(14) . . ? N1 C16 O3 110.53(14) . . ? C17 C16 O3 121.66(13) . . ? C16 C17 C20 118.80(14) . . ? C16 C17 C6 123.82(13) . . ? C20 C17 C6 116.87(13) . . ? C10 C18 C19 121.41(15) . . ? C10 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C18 C19 C7 120.84(14) . . ? C18 C19 H19 119.6 . . ? C7 C19 H19 119.6 . . ? N2 C20 C17 177.70(18) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.66 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.184 _refine_diff_density_min -0.125 _refine_diff_density_rms 0.029 _database_code_depnum_ccdc_archive 'CCDC 946297' ####################################################################### # # 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_ppp _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H16 N2 O' _chemical_formula_weight 312.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.0929(3) _cell_length_b 6.3370(2) _cell_length_c 12.8314(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.1920(10) _cell_angle_gamma 90.00 _cell_volume 807.73(4) _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 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.984 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13705 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 33.40 _reflns_number_total 5814 _reflns_number_gt 5076 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1561P)^2^+0.0397P] 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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.031(9) _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 0.1(12) _refine_ls_number_reflns 5814 _refine_ls_number_parameters 219 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1582 _refine_ls_wR_factor_gt 0.1422 _refine_ls_goodness_of_fit_ref 0.785 _refine_ls_restrained_S_all 0.784 _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 0.05727(11) 0.40889(18) 0.70460(8) 0.0455(2) Uani 1 1 d . . . C23 C 0.19129(10) 0.16350(18) 0.62071(7) 0.03115(19) Uani 1 1 d . . . C24 C 0.19601(11) 0.00391(17) 0.70859(8) 0.03073(18) Uani 1 1 d . . . H24 H 0.1640 -0.1308 0.6759 0.037 Uiso 1 1 calc R . . C1 C 0.3743(2) 0.0487(4) 0.35247(13) 0.0630(5) Uani 1 1 d . . . H1 H 0.4141 0.0232 0.2937 0.076 Uiso 1 1 calc R . . C2 C 0.38882(19) -0.0989(3) 0.43544(13) 0.0566(4) Uani 1 1 d . . . H2 H 0.4386 -0.2213 0.4315 0.068 Uiso 1 1 calc R . . C3 C 0.32966(14) -0.0630(2) 0.52254(10) 0.0429(3) Uani 1 1 d . . . H3 H 0.3397 -0.1621 0.5768 0.051 Uiso 1 1 calc R . . C4 C 0.25392(12) 0.1220(2) 0.53097(8) 0.0348(2) Uani 1 1 d . . . C5 C 0.33600(11) -0.03367(19) 0.77301(8) 0.0330(2) Uani 1 1 d . . . C6 C 0.43323(13) 0.1233(2) 0.79104(10) 0.0421(3) Uani 1 1 d . . . H6 H 0.4150 0.2557 0.7606 0.050 Uiso 1 1 calc R . . C7 C 0.55783(14) 0.0848(3) 0.85429(11) 0.0496(3) Uani 1 1 d . . . H7 H 0.6218 0.1919 0.8653 0.060 Uiso 1 1 calc R . . C8 C 0.58822(14) -0.1102(3) 0.90108(10) 0.0474(3) Uani 1 1 d . . . C9 C 0.72207(19) -0.1516(5) 0.97102(17) 0.0734(6) Uani 1 1 d . . . H9A H 0.7077 -0.1994 1.0391 0.110 Uiso 1 1 calc R . . H9B H 0.7740 -0.0239 0.9793 0.110 Uiso 1 1 calc R . . H9C H 0.7698 -0.2579 0.9392 0.110 Uiso 1 1 calc R . . C10 C 0.30170(19) 0.2302(3) 0.35755(11) 0.0577(4) Uani 1 1 d . . . H10 H 0.2929 0.3268 0.3022 0.069 Uiso 1 1 calc R . . C11 C 0.23982(14) 0.2718(2) 0.44664(9) 0.0419(3) Uani 1 1 d . . . C12 C 0.36645(14) -0.2313(2) 0.81910(10) 0.0423(3) Uani 1 1 d . . . H12 H 0.3030 -0.3391 0.8072 0.051 Uiso 1 1 calc R . . C13 C 0.49089(16) -0.2684(3) 0.88278(11) 0.0486(3) Uani 1 1 d . . . H13 H 0.5093 -0.4005 0.9135 0.058 Uiso 1 1 calc R . . C14 C 0.09903(11) 0.0695(2) 0.78073(8) 0.0346(2) Uani 1 1 d . . . C15 C 0.04089(12) 0.2627(2) 0.77829(9) 0.0377(2) Uani 1 1 d . . . C16 C 0.12164(12) 0.34916(19) 0.62206(8) 0.0348(2) Uani 1 1 d . . . C17 C 0.10684(14) 0.4980(2) 0.53921(9) 0.0422(3) Uani 1 1 d . . . H17 H 0.0582 0.6214 0.5434 0.051 Uiso 1 1 calc R . . C18 C 0.16462(15) 0.4587(2) 0.45294(10) 0.0457(3) Uani 1 1 d . . . H18 H 0.1546 0.5555 0.3976 0.055 Uiso 1 1 calc R . . N3 N -0.04056(14) 0.3356(3) 0.84305(11) 0.0546(3) Uani 1 1 d . . . H19A H -0.0742 0.4603 0.8340 0.066 Uiso 1 1 calc R . . H19B H -0.0589 0.2572 0.8934 0.066 Uiso 1 1 calc R . . C20 C 0.07227(14) -0.0744(2) 0.85800(10) 0.0438(3) Uani 1 1 d . . . N4 N 0.05044(19) -0.1943(3) 0.92038(13) 0.0657(4) 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 O1 0.0589(6) 0.0398(5) 0.0402(4) 0.0015(4) 0.0153(4) 0.0098(4) C23 0.0328(4) 0.0342(5) 0.0260(4) 0.0011(3) 0.0041(3) -0.0016(4) C24 0.0338(4) 0.0320(5) 0.0269(4) 0.0004(3) 0.0067(3) -0.0013(3) C1 0.0765(11) 0.0739(12) 0.0470(7) -0.0011(7) 0.0342(8) -0.0029(9) C2 0.0633(9) 0.0621(9) 0.0515(7) -0.0026(7) 0.0292(7) 0.0036(7) C3 0.0479(6) 0.0450(7) 0.0386(5) 0.0008(4) 0.0158(4) 0.0005(5) C4 0.0367(5) 0.0398(5) 0.0284(4) 0.0010(4) 0.0076(3) -0.0045(4) C5 0.0355(4) 0.0357(5) 0.0283(4) 0.0026(3) 0.0072(3) 0.0024(4) C6 0.0383(5) 0.0416(6) 0.0445(5) 0.0054(5) 0.0024(4) -0.0022(5) C7 0.0374(6) 0.0607(9) 0.0483(6) 0.0016(6) 0.0011(5) -0.0031(6) C8 0.0392(6) 0.0678(9) 0.0351(5) 0.0037(5) 0.0063(4) 0.0130(6) C9 0.0453(8) 0.1052(18) 0.0646(10) 0.0120(11) -0.0038(7) 0.0204(10) C10 0.0697(9) 0.0711(10) 0.0362(5) 0.0082(6) 0.0203(6) -0.0085(8) C11 0.0457(6) 0.0496(7) 0.0303(4) 0.0055(4) 0.0059(4) -0.0067(5) C12 0.0469(6) 0.0386(6) 0.0418(5) 0.0085(4) 0.0087(4) 0.0042(5) C13 0.0531(7) 0.0515(8) 0.0417(5) 0.0107(5) 0.0099(5) 0.0166(6) C14 0.0354(5) 0.0393(5) 0.0302(4) -0.0008(4) 0.0084(3) -0.0031(4) C15 0.0387(5) 0.0420(6) 0.0328(4) -0.0039(4) 0.0077(4) -0.0003(4) C16 0.0388(5) 0.0345(5) 0.0300(4) 0.0008(3) 0.0030(3) 0.0000(4) C17 0.0485(6) 0.0387(6) 0.0362(5) 0.0053(4) -0.0012(4) 0.0006(5) C18 0.0540(7) 0.0467(7) 0.0341(5) 0.0115(5) 0.0012(4) -0.0042(6) N3 0.0613(8) 0.0563(8) 0.0523(6) -0.0034(5) 0.0262(6) 0.0102(6) C20 0.0495(6) 0.0435(7) 0.0430(6) 0.0009(5) 0.0209(5) -0.0002(5) N4 0.0843(11) 0.0585(9) 0.0664(8) 0.0151(7) 0.0464(8) 0.0083(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C15 1.3544(16) . ? O1 C16 1.3894(14) . ? C23 C16 1.3722(16) . ? C23 C4 1.4325(14) . ? C23 C24 1.5091(14) . ? C24 C14 1.5194(14) . ? C24 C5 1.5241(15) . ? C24 H24 0.9800 . ? C1 C10 1.371(3) . ? C1 C2 1.405(3) . ? C1 H1 0.9300 . ? C2 C3 1.3762(17) . ? C2 H2 0.9300 . ? C3 C4 1.4141(19) . ? C3 H3 0.9300 . ? C4 C11 1.4274(15) . ? C5 C6 1.3878(17) . ? C5 C12 1.3958(16) . ? C6 C7 1.3924(17) . ? C6 H6 0.9300 . ? C7 C8 1.384(2) . ? C7 H7 0.9300 . ? C8 C13 1.394(3) . ? C8 C9 1.507(2) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.4209(18) . ? C10 H10 0.9300 . ? C11 C18 1.417(2) . ? C12 C13 1.3918(19) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.3560(18) . ? C14 C20 1.4077(17) . ? C15 N3 1.3495(16) . ? C16 C17 1.4092(16) . ? C17 C18 1.362(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? N3 H19A 0.8600 . ? N3 H19B 0.8600 . ? C20 N4 1.153(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O1 C16 118.50(11) . . ? C16 C23 C4 117.86(10) . . ? C16 C23 C24 120.91(9) . . ? C4 C23 C24 121.17(10) . . ? C23 C24 C14 109.47(9) . . ? C23 C24 C5 114.43(8) . . ? C14 C24 C5 110.34(8) . . ? C23 C24 H24 107.4 . . ? C14 C24 H24 107.4 . . ? C5 C24 H24 107.4 . . ? C10 C1 C2 120.50(13) . . ? C10 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C3 C2 C1 120.18(17) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 121.17(14) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C11 118.42(10) . . ? C3 C4 C23 122.34(10) . . ? C11 C4 C23 119.24(11) . . ? C6 C5 C12 118.45(11) . . ? C6 C5 C24 122.59(11) . . ? C12 C5 C24 118.91(11) . . ? C5 C6 C7 120.70(13) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 121.15(15) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C13 118.25(12) . . ? C7 C8 C9 121.35(18) . . ? C13 C8 C9 120.39(18) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C10 C11 120.56(15) . . ? C1 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C18 C11 C10 121.15(13) . . ? C18 C11 C4 119.68(11) . . ? C10 C11 C4 119.17(14) . . ? C13 C12 C5 120.57(13) . . ? C13 C12 H12 119.7 . . ? C5 C12 H12 119.7 . . ? C12 C13 C8 120.87(14) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? C15 C14 C20 117.71(10) . . ? C15 C14 C24 123.76(10) . . ? C20 C14 C24 118.47(11) . . ? N3 C15 O1 111.04(13) . . ? N3 C15 C14 127.08(12) . . ? O1 C15 C14 121.87(10) . . ? C23 C16 O1 123.57(10) . . ? C23 C16 C17 123.39(11) . . ? O1 C16 C17 113.04(11) . . ? C18 C17 C16 119.16(13) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C11 120.65(11) . . ? C17 C18 H18 119.7 . . ? C11 C18 H18 119.7 . . ? C15 N3 H19A 120.0 . . ? C15 N3 H19B 120.0 . . ? H19A N3 H19B 120.0 . . ? N4 C20 C14 179.10(16) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 33.40 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.336 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 946296' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H17 N O5' _chemical_formula_weight 423.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.937(5) _cell_length_b 11.638(9) _cell_length_c 13.019(10) _cell_angle_alpha 75.535(8) _cell_angle_beta 89.874(9) _cell_angle_gamma 76.165(8) _cell_volume 986.3(13) _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 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5391 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 24.10 _reflns_number_total 2995 _reflns_number_gt 1899 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1330P)^2^+0.4841P] 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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.030(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2995 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0998 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.2145 _refine_ls_wR_factor_gt 0.1788 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _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 -0.0536(8) 1.0095(4) 0.6188(4) 0.1328(17) Uani 1 1 d . . . O2 O -0.3101(9) 0.9407(4) 0.5975(4) 0.1366(19) Uani 1 1 d . . . O3 O -0.0949(3) 0.3918(2) 0.9546(2) 0.0544(7) Uani 1 1 d . . . H3 H -0.1820 0.3541 0.9634 0.082 Uiso 1 1 calc R . . O4 O 0.0425(3) 0.2915(2) 0.83508(18) 0.0523(7) Uani 1 1 d . . . O5 O 0.5898(4) 0.2877(3) 1.0013(2) 0.0774(10) Uani 1 1 d . . . C32 C 0.0795(5) 0.3172(3) 0.9344(3) 0.0445(9) Uani 1 1 d . . . N4 N -0.1420(10) 0.9278(4) 0.6290(4) 0.0989(15) Uani 1 1 d . . . C2 C -0.0285(8) 0.8028(4) 0.6831(3) 0.0706(13) Uani 1 1 d . . . C3 C -0.1167(7) 0.7085(4) 0.6940(3) 0.0707(12) Uani 1 1 d . . . H3A H -0.2485 0.7227 0.6699 0.085 Uiso 1 1 calc R . . C4 C -0.0082(6) 0.5917(4) 0.7411(3) 0.0612(11) Uani 1 1 d . . . H4 H -0.0672 0.5265 0.7481 0.073 Uiso 1 1 calc R . . C5 C 0.1861(5) 0.5695(3) 0.7782(3) 0.0487(9) Uani 1 1 d . . . C6 C 0.3108(5) 0.4420(3) 0.8259(3) 0.0460(9) Uani 1 1 d . . . H6 H 0.4468 0.4491 0.8365 0.055 Uiso 1 1 calc R . . C7 C 0.2492(5) 0.3803(3) 0.9339(3) 0.0463(9) Uani 1 1 d . . . H7 H 0.2114 0.4420 0.9744 0.056 Uiso 1 1 calc R . . C8 C 0.4208(5) 0.2794(4) 0.9956(3) 0.0512(10) Uani 1 1 d . . . C9 C 0.3458(5) 0.1748(3) 1.0468(3) 0.0500(9) Uani 1 1 d . . . C10 C 0.4457(6) 0.0669(4) 1.1176(3) 0.0687(12) Uani 1 1 d . . . H10 H 0.5793 0.0532 1.1382 0.082 Uiso 1 1 calc R . . C11 C 0.3409(7) -0.0188(4) 1.1563(4) 0.0719(13) Uani 1 1 d . . . H11 H 0.4034 -0.0923 1.2041 0.086 Uiso 1 1 calc R . . C12 C 0.1851(5) 0.2887(3) 0.7631(3) 0.0453(9) Uani 1 1 d . . . C13 C 0.1803(6) 0.2124(3) 0.6954(3) 0.0546(10) Uani 1 1 d . . . H13 H 0.0861 0.1664 0.7023 0.066 Uiso 1 1 calc R . . C14 C 0.3135(6) 0.2067(4) 0.6203(3) 0.0608(11) Uani 1 1 d . . . H14 H 0.3110 0.1553 0.5761 0.073 Uiso 1 1 calc R . . C15 C 0.4559(6) 0.2759(3) 0.6068(3) 0.0517(10) Uani 1 1 d . . . C16 C 0.5970(7) 0.2688(4) 0.5298(3) 0.0660(12) Uani 1 1 d . . . H16 H 0.5971 0.2163 0.4863 0.079 Uiso 1 1 calc R . . C17 C 0.7319(6) 0.3361(4) 0.5173(3) 0.0708(13) Uani 1 1 d . . . H17 H 0.8240 0.3301 0.4657 0.085 Uiso 1 1 calc R . . C18 C 0.7334(6) 0.4147(4) 0.5819(3) 0.0658(12) Uani 1 1 d . . . H18 H 0.8259 0.4620 0.5727 0.079 Uiso 1 1 calc R . . C19 C 0.6018(5) 0.4231(4) 0.6578(3) 0.0554(10) Uani 1 1 d . . . H19 H 0.6057 0.4758 0.7006 0.066 Uiso 1 1 calc R . . C20 C 0.4586(5) 0.3536(3) 0.6736(3) 0.0465(9) Uani 1 1 d . . . C21 C 0.3192(5) 0.3592(3) 0.7527(3) 0.0442(9) Uani 1 1 d . . . C22 C 0.1496(5) 0.1962(3) 1.0161(3) 0.0438(9) Uani 1 1 d . . . C23 C 0.0454(6) 0.1099(4) 1.0557(3) 0.0567(10) Uani 1 1 d . . . H23 H -0.0886 0.1237 1.0359 0.068 Uiso 1 1 calc R . . C24 C 0.1449(7) 0.0031(4) 1.1250(3) 0.0694(12) Uani 1 1 d . . . H24 H 0.0767 -0.0567 1.1518 0.083 Uiso 1 1 calc R . . C25 C 0.2678(7) 0.6689(4) 0.7670(3) 0.0648(12) Uani 1 1 d . . . H25 H 0.3984 0.6562 0.7924 0.078 Uiso 1 1 calc R . . C26 C 0.1618(8) 0.7853(4) 0.7195(4) 0.0755(13) Uani 1 1 d . . . H26 H 0.2191 0.8512 0.7124 0.091 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 0.202(5) 0.057(2) 0.127(3) -0.010(2) -0.009(3) -0.022(3) O2 0.171(5) 0.085(3) 0.127(4) -0.031(3) -0.055(4) 0.023(3) O3 0.0331(14) 0.0546(16) 0.0785(18) -0.0190(13) 0.0139(12) -0.0148(12) O4 0.0429(14) 0.0704(17) 0.0507(15) -0.0135(12) 0.0066(12) -0.0298(13) O5 0.0417(16) 0.099(2) 0.085(2) 0.0030(17) -0.0044(14) -0.0314(15) C32 0.0356(19) 0.057(2) 0.046(2) -0.0151(17) 0.0091(15) -0.0182(17) N4 0.146(5) 0.065(3) 0.076(3) -0.019(2) -0.013(3) -0.005(3) C2 0.107(4) 0.042(3) 0.055(3) -0.0114(19) 0.008(3) -0.006(2) C3 0.064(3) 0.066(3) 0.071(3) -0.011(2) 0.006(2) -0.002(2) C4 0.054(3) 0.055(3) 0.073(3) -0.009(2) 0.011(2) -0.018(2) C5 0.053(2) 0.049(2) 0.047(2) -0.0116(17) 0.0135(18) -0.0184(18) C6 0.0357(19) 0.057(2) 0.051(2) -0.0127(17) 0.0120(16) -0.0221(17) C7 0.041(2) 0.052(2) 0.049(2) -0.0116(17) 0.0108(16) -0.0191(17) C8 0.033(2) 0.071(3) 0.052(2) -0.0116(18) 0.0073(16) -0.0211(18) C9 0.042(2) 0.056(2) 0.051(2) -0.0074(18) 0.0037(17) -0.0144(18) C10 0.056(3) 0.069(3) 0.071(3) 0.000(2) -0.001(2) -0.014(2) C11 0.073(3) 0.061(3) 0.069(3) 0.008(2) -0.002(2) -0.018(2) C12 0.043(2) 0.051(2) 0.042(2) -0.0084(16) 0.0038(16) -0.0169(17) C13 0.059(2) 0.054(2) 0.053(2) -0.0102(18) 0.001(2) -0.0228(19) C14 0.078(3) 0.055(2) 0.051(2) -0.0148(19) 0.003(2) -0.017(2) C15 0.052(2) 0.052(2) 0.041(2) -0.0050(17) 0.0039(18) -0.0016(18) C16 0.074(3) 0.064(3) 0.049(2) -0.011(2) 0.011(2) -0.001(2) C17 0.060(3) 0.087(3) 0.051(2) -0.008(2) 0.019(2) -0.001(2) C18 0.048(2) 0.085(3) 0.058(2) -0.006(2) 0.018(2) -0.017(2) C19 0.049(2) 0.062(2) 0.052(2) -0.0088(18) 0.0125(19) -0.0131(19) C20 0.041(2) 0.048(2) 0.042(2) -0.0009(16) 0.0026(16) -0.0061(16) C21 0.042(2) 0.046(2) 0.0428(19) -0.0069(15) 0.0054(16) -0.0128(16) C22 0.039(2) 0.051(2) 0.0433(19) -0.0129(16) 0.0097(16) -0.0149(16) C23 0.050(2) 0.057(2) 0.063(2) -0.006(2) 0.0071(19) -0.0231(19) C24 0.080(3) 0.056(3) 0.071(3) -0.001(2) 0.010(2) -0.031(2) C25 0.080(3) 0.060(3) 0.061(3) -0.015(2) 0.006(2) -0.032(2) C26 0.114(4) 0.050(3) 0.067(3) -0.014(2) 0.003(3) -0.030(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 N4 1.231(6) . ? O2 N4 1.200(6) . ? O3 C32 1.377(4) . ? O3 H3 0.8200 . ? O4 C12 1.362(4) . ? O4 C32 1.435(4) . ? O5 C8 1.204(4) . ? C32 C22 1.509(5) . ? C32 C7 1.529(5) . ? N4 C2 1.474(6) . ? C2 C26 1.354(7) . ? C2 C3 1.357(6) . ? C3 C4 1.374(6) . ? C3 H3A 0.9300 . ? C4 C5 1.374(5) . ? C4 H4 0.9300 . ? C5 C25 1.381(5) . ? C5 C6 1.505(5) . ? C6 C21 1.507(5) . ? C6 C7 1.521(5) . ? C6 H6 0.9800 . ? C7 C8 1.518(5) . ? C7 H7 0.9800 . ? C8 C9 1.447(5) . ? C9 C22 1.365(5) . ? C9 C10 1.384(5) . ? C10 C11 1.368(6) . ? C10 H10 0.9300 . ? C11 C24 1.366(6) . ? C11 H11 0.9300 . ? C12 C21 1.366(5) . ? C12 C13 1.404(5) . ? C13 C14 1.346(5) . ? C13 H13 0.9300 . ? C14 C15 1.402(6) . ? C14 H14 0.9300 . ? C15 C16 1.403(5) . ? C15 C20 1.405(5) . ? C16 C17 1.342(6) . ? C16 H16 0.9300 . ? C17 C18 1.390(6) . ? C17 H17 0.9300 . ? C18 C19 1.350(5) . ? C18 H18 0.9300 . ? C19 C20 1.408(5) . ? C19 H19 0.9300 . ? C20 C21 1.414(5) . ? C22 C23 1.373(5) . ? C23 C24 1.367(6) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.365(6) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C32 O3 H3 109.5 . . ? C12 O4 C32 120.0(2) . . ? O3 C32 O4 106.3(3) . . ? O3 C32 C22 115.3(3) . . ? O4 C32 C22 107.5(3) . . ? O3 C32 C7 109.7(3) . . ? O4 C32 C7 113.7(3) . . ? C22 C32 C7 104.5(3) . . ? O2 N4 O1 125.8(5) . . ? O2 N4 C2 117.6(5) . . ? O1 N4 C2 116.6(6) . . ? C26 C2 C3 121.9(4) . . ? C26 C2 N4 119.0(5) . . ? C3 C2 N4 119.2(5) . . ? C2 C3 C4 119.0(4) . . ? C2 C3 H3A 120.5 . . ? C4 C3 H3A 120.5 . . ? C3 C4 C5 121.1(4) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C25 117.7(4) . . ? C4 C5 C6 122.1(3) . . ? C25 C5 C6 120.1(4) . . ? C5 C6 C21 112.6(3) . . ? C5 C6 C7 114.3(3) . . ? C21 C6 C7 109.1(3) . . ? C5 C6 H6 106.8 . . ? C21 C6 H6 106.8 . . ? C7 C6 H6 106.8 . . ? C8 C7 C6 111.0(3) . . ? C8 C7 C32 104.0(3) . . ? C6 C7 C32 116.9(3) . . ? C8 C7 H7 108.2 . . ? C6 C7 H7 108.2 . . ? C32 C7 H7 108.2 . . ? O5 C8 C9 126.5(4) . . ? O5 C8 C7 124.7(3) . . ? C9 C8 C7 108.8(3) . . ? C22 C9 C10 121.8(3) . . ? C22 C9 C8 109.6(3) . . ? C10 C9 C8 128.6(3) . . ? C11 C10 C9 117.6(4) . . ? C11 C10 H10 121.2 . . ? C9 C10 H10 121.2 . . ? C24 C11 C10 120.3(4) . . ? C24 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? O4 C12 C21 123.0(3) . . ? O4 C12 C13 115.6(3) . . ? C21 C12 C13 121.3(3) . . ? C14 C13 C12 119.3(3) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 121.9(4) . . ? C13 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? C14 C15 C16 122.1(4) . . ? C14 C15 C20 118.8(3) . . ? C16 C15 C20 119.1(4) . . ? C17 C16 C15 121.5(4) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C17 C18 119.7(4) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C19 C18 C17 120.6(4) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 121.3(4) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C15 C20 C19 117.7(3) . . ? C15 C20 C21 119.3(3) . . ? C19 C20 C21 122.9(3) . . ? C12 C21 C20 119.4(3) . . ? C12 C21 C6 118.3(3) . . ? C20 C21 C6 122.3(3) . . ? C9 C22 C23 120.2(3) . . ? C9 C22 C32 111.3(3) . . ? C23 C22 C32 128.5(3) . . ? C24 C23 C22 117.9(4) . . ? C24 C23 H23 121.1 . . ? C22 C23 H23 121.1 . . ? C11 C24 C23 122.3(4) . . ? C11 C24 H24 118.9 . . ? C23 C24 H24 118.9 . . ? C26 C25 C5 121.7(4) . . ? C26 C25 H25 119.2 . . ? C5 C25 H25 119.2 . . ? C2 C26 C25 118.7(4) . . ? C2 C26 H26 120.7 . . ? C25 C26 H26 120.7 . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 24.10 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.288 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 946298' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H27 N3 O3' _chemical_formula_weight 381.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6867(5) _cell_length_b 11.0032(7) _cell_length_c 12.0059(7) _cell_angle_alpha 70.060(2) _cell_angle_beta 84.209(2) _cell_angle_gamma 76.001(2) _cell_volume 1046.50(11) _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 yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10726 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 23.97 _reflns_number_total 3236 _reflns_number_gt 2623 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1288P)^2^+0.3624P] 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 0.024(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3236 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1864 _refine_ls_wR_factor_gt 0.1683 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _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 0.7800(2) 0.7461(2) -0.05727(15) 0.0684(6) Uani 1 1 d . . . O1S O 0.7046(3) 0.8110(2) -0.2996(2) 0.1017(8) Uani 1 1 d . . . O2 O 0.50304(18) 0.51328(19) 0.30615(16) 0.0644(5) Uani 1 1 d . . . N1 N 0.5619(3) 0.9795(2) 0.2836(2) 0.0650(6) Uani 1 1 d . . . N2 N 1.0523(2) 0.48711(17) 0.29417(16) 0.0439(5) Uani 1 1 d . . . N3 N 1.1955(2) 0.4294(2) 0.36089(18) 0.0549(5) Uani 1 1 d . . . H31 H 1.250(4) 0.353(3) 0.334(3) 0.082 Uiso 1 1 d . . . H32 H 1.264(4) 0.495(3) 0.339(3) 0.082 Uiso 1 1 d . . . C1 C 0.5249(3) 0.9676(3) 0.1847(2) 0.0684(8) Uani 1 1 d . . . H1 H 0.4544 1.0381 0.1346 0.082 Uiso 1 1 calc R . . C2 C 0.5841(3) 0.8571(2) 0.1506(2) 0.0584(7) Uani 1 1 d . . . H2 H 0.5540 0.8551 0.0792 0.070 Uiso 1 1 calc R . . C3 C 0.6875(2) 0.7502(2) 0.22240(19) 0.0428(5) Uani 1 1 d . . . C4 C 0.7533(2) 0.6253(2) 0.18935(19) 0.0416(5) Uani 1 1 d . . . H4 H 0.6767 0.6188 0.1382 0.050 Uiso 1 1 calc R . . C5 C 0.7747(2) 0.5029(2) 0.29708(19) 0.0401(5) Uani 1 1 d . . . C6 C 0.9172(2) 0.4433(2) 0.34819(19) 0.0397(5) Uani 1 1 d . . . C7 C 0.9392(3) 0.3298(2) 0.4623(2) 0.0502(6) Uani 1 1 d . . . H7A H 0.9461 0.3635 0.5261 0.060 Uiso 1 1 calc R . . H7B H 1.0393 0.2688 0.4579 0.060 Uiso 1 1 calc R . . C8 C 0.8065(3) 0.2532(2) 0.4928(2) 0.0511(6) Uani 1 1 d . . . C9 C 0.8199(4) 0.1658(3) 0.6225(2) 0.0779(9) Uani 1 1 d . . . H9A H 0.9245 0.1100 0.6361 0.117 Uiso 1 1 calc R . . H9B H 0.7430 0.1118 0.6410 0.117 Uiso 1 1 calc R . . H9C H 0.8007 0.2207 0.6720 0.117 Uiso 1 1 calc R . . C10 C 0.6595(3) 0.8763(3) 0.3535(3) 0.0693(8) Uani 1 1 d . . . H10 H 0.6862 0.8814 0.4246 0.083 Uiso 1 1 calc R . . C11 C 0.7242(3) 0.7613(3) 0.3278(3) 0.0642(7) Uani 1 1 d . . . H11 H 0.7921 0.6916 0.3807 0.077 Uiso 1 1 calc R . . C12 C 0.6321(3) 0.4582(2) 0.3528(2) 0.0462(6) Uani 1 1 d . . . C13 C 0.6466(3) 0.3522(3) 0.4716(2) 0.0595(7) Uani 1 1 d . . . H13A H 0.5638 0.3040 0.4803 0.071 Uiso 1 1 calc R . . H13B H 0.6283 0.3940 0.5324 0.071 Uiso 1 1 calc R . . C14 C 1.0509(2) 0.5679(2) 0.17692(19) 0.0412(5) Uani 1 1 d . . . C15 C 1.2082(3) 0.5781(2) 0.1134(2) 0.0520(6) Uani 1 1 d . . . H15A H 1.2504 0.4986 0.0924 0.062 Uiso 1 1 calc R . . H15B H 1.2817 0.5820 0.1672 0.062 Uiso 1 1 calc R . . C16 C 1.1987(3) 0.6990(2) 0.0013(2) 0.0493(6) Uani 1 1 d . . . C17 C 1.0619(3) 0.7053(2) -0.0724(2) 0.0529(6) Uani 1 1 d . . . H17A H 1.0470 0.7874 -0.1388 0.063 Uiso 1 1 calc R . . H17B H 1.0907 0.6327 -0.1043 0.063 Uiso 1 1 calc R . . C18 C 0.9072(3) 0.6980(2) -0.0045(2) 0.0474(6) Uani 1 1 d . . . C19 C 0.9099(2) 0.6297(2) 0.12149(19) 0.0408(5) Uani 1 1 d . . . C20 C 1.1711(4) 0.8256(3) 0.0334(3) 0.0722(8) Uani 1 1 d . . . H20A H 1.2565 0.8201 0.0810 0.108 Uiso 1 1 calc R . . H20B H 1.0727 0.8360 0.0770 0.108 Uiso 1 1 calc R . . H20C H 1.1667 0.9005 -0.0378 0.108 Uiso 1 1 calc R . . C21 C 1.3553(3) 0.6835(3) -0.0690(2) 0.0646(7) Uani 1 1 d . . . H21A H 1.3492 0.7575 -0.1410 0.097 Uiso 1 1 calc R . . H21B H 1.3743 0.6029 -0.0876 0.097 Uiso 1 1 calc R . . H21C H 1.4406 0.6803 -0.0223 0.097 Uiso 1 1 calc R . . C22 C 0.8225(4) 0.1666(3) 0.4146(3) 0.0790(9) Uani 1 1 d . . . H22A H 0.8040 0.2220 0.3337 0.118 Uiso 1 1 calc R . . H22B H 0.7462 0.1119 0.4400 0.118 Uiso 1 1 calc R . . H22C H 0.9275 0.1113 0.4210 0.118 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 0.0519(11) 0.0936(13) 0.0446(10) -0.0111(9) -0.0128(8) -0.0007(9) O1S 0.1197(19) 0.0906(16) 0.0819(16) -0.0416(13) -0.0116(13) 0.0236(14) O2 0.0328(9) 0.0901(13) 0.0674(12) -0.0192(10) -0.0021(8) -0.0174(8) N1 0.0693(14) 0.0483(12) 0.0695(15) -0.0169(11) -0.0017(12) -0.0020(10) N2 0.0305(9) 0.0489(10) 0.0445(11) -0.0048(8) -0.0051(7) -0.0081(7) N3 0.0373(11) 0.0666(13) 0.0540(13) -0.0111(10) -0.0090(9) -0.0084(9) C1 0.0722(18) 0.0528(14) 0.0548(17) -0.0032(12) -0.0033(13) 0.0126(13) C2 0.0591(15) 0.0597(14) 0.0417(14) -0.0088(11) -0.0064(11) 0.0045(12) C3 0.0324(11) 0.0452(11) 0.0461(13) -0.0087(9) -0.0019(9) -0.0086(9) C4 0.0296(11) 0.0478(11) 0.0460(13) -0.0130(9) -0.0049(9) -0.0077(9) C5 0.0345(11) 0.0426(11) 0.0435(12) -0.0153(9) 0.0005(9) -0.0079(9) C6 0.0324(11) 0.0418(11) 0.0438(12) -0.0132(9) 0.0018(9) -0.0087(8) C7 0.0459(13) 0.0519(13) 0.0448(13) -0.0088(10) 0.0014(10) -0.0077(10) C8 0.0540(14) 0.0489(12) 0.0470(14) -0.0109(10) 0.0088(10) -0.0159(10) C9 0.086(2) 0.0790(19) 0.0547(17) -0.0001(14) 0.0099(15) -0.0295(16) C10 0.0722(18) 0.0597(15) 0.0798(19) -0.0314(14) -0.0227(15) -0.0011(13) C11 0.0602(16) 0.0560(14) 0.0741(18) -0.0221(13) -0.0285(13) 0.0032(12) C12 0.0362(12) 0.0557(13) 0.0522(14) -0.0241(11) 0.0060(10) -0.0137(10) C13 0.0473(14) 0.0715(16) 0.0572(16) -0.0164(13) 0.0117(11) -0.0210(12) C14 0.0364(12) 0.0437(11) 0.0418(13) -0.0110(9) -0.0014(9) -0.0099(9) C15 0.0360(12) 0.0639(14) 0.0509(14) -0.0114(11) 0.0018(10) -0.0134(10) C16 0.0468(13) 0.0534(13) 0.0453(13) -0.0121(10) 0.0053(10) -0.0150(10) C17 0.0510(14) 0.0610(14) 0.0416(13) -0.0137(11) 0.0019(10) -0.0091(11) C18 0.0465(13) 0.0507(12) 0.0435(13) -0.0159(10) -0.0067(10) -0.0050(10) C19 0.0360(11) 0.0436(11) 0.0413(12) -0.0118(9) -0.0029(9) -0.0082(9) C20 0.0786(19) 0.0706(17) 0.0778(19) -0.0300(15) 0.0146(15) -0.0340(15) C21 0.0534(15) 0.0790(17) 0.0568(16) -0.0151(13) 0.0121(12) -0.0220(13) C22 0.108(2) 0.0543(15) 0.077(2) -0.0234(14) 0.0027(17) -0.0216(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C18 1.237(3) . ? O2 C12 1.227(3) . ? N1 C1 1.317(4) . ? N1 C10 1.319(3) . ? N2 C14 1.384(3) . ? N2 C6 1.392(3) . ? N2 N3 1.437(2) . ? N3 H31 1.00(3) . ? N3 H32 1.00(3) . ? C1 C2 1.380(4) . ? C1 H1 0.9300 . ? C2 C3 1.374(3) . ? C2 H2 0.9300 . ? C3 C11 1.387(3) . ? C3 C4 1.523(3) . ? C4 C5 1.503(3) . ? C4 C19 1.516(3) . ? C4 H4 0.9800 . ? C5 C6 1.351(3) . ? C5 C12 1.458(3) . ? C6 C7 1.498(3) . ? C7 C8 1.532(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.525(3) . ? C8 C13 1.526(3) . ? C8 C22 1.526(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.378(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.497(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C19 1.363(3) . ? C14 C15 1.505(3) . ? C15 C16 1.529(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C20 1.527(4) . ? C16 C17 1.527(3) . ? C16 C21 1.531(3) . ? C17 C18 1.504(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.441(3) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C10 116.1(2) . . ? C14 N2 C6 120.72(17) . . ? C14 N2 N3 122.47(17) . . ? C6 N2 N3 116.25(17) . . ? N2 N3 H31 105.5(18) . . ? N2 N3 H32 109.1(17) . . ? H31 N3 H32 108(3) . . ? N1 C1 C2 124.2(2) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C3 C2 C1 119.8(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C11 116.1(2) . . ? C2 C3 C4 121.6(2) . . ? C11 C3 C4 122.26(19) . . ? C5 C4 C19 109.19(16) . . ? C5 C4 C3 111.49(17) . . ? C19 C4 C3 111.92(16) . . ? C5 C4 H4 108.0 . . ? C19 C4 H4 108.0 . . ? C3 C4 H4 108.0 . . ? C6 C5 C12 120.41(19) . . ? C6 C5 C4 122.01(18) . . ? C12 C5 C4 117.27(18) . . ? C5 C6 N2 119.80(18) . . ? C5 C6 C7 123.17(19) . . ? N2 C6 C7 117.03(18) . . ? C6 C7 C8 114.21(19) . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C13 110.4(2) . . ? C9 C8 C22 109.5(2) . . ? C13 C8 C22 109.4(2) . . ? C9 C8 C7 108.6(2) . . ? C13 C8 C7 108.91(18) . . ? C22 C8 C7 110.0(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 C11 124.1(3) . . ? N1 C10 H10 118.0 . . ? C11 C10 H10 118.0 . . ? C10 C11 C3 119.6(2) . . ? C10 C11 H11 120.2 . . ? C3 C11 H11 120.2 . . ? O2 C12 C5 120.0(2) . . ? O2 C12 C13 121.59(19) . . ? C5 C12 C13 118.2(2) . . ? C12 C13 C8 114.72(19) . . ? C12 C13 H13A 108.6 . . ? C8 C13 H13A 108.6 . . ? C12 C13 H13B 108.6 . . ? C8 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C19 C14 N2 119.79(18) . . ? C19 C14 C15 122.4(2) . . ? N2 C14 C15 117.79(18) . . ? C14 C15 C16 113.69(19) . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15B 108.8 . . ? C16 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C20 C16 C17 110.0(2) . . ? C20 C16 C15 110.4(2) . . ? C17 C16 C15 108.29(19) . . ? C20 C16 C21 109.3(2) . . ? C17 C16 C21 110.0(2) . . ? C15 C16 C21 108.8(2) . . ? C18 C17 C16 114.07(19) . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17B 108.7 . . ? C16 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? O1 C18 C19 120.8(2) . . ? O1 C18 C17 120.2(2) . . ? C19 C18 C17 119.04(19) . . ? C14 C19 C18 120.15(19) . . ? C14 C19 C4 121.25(19) . . ? C18 C19 C4 118.58(18) . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C8 C22 H22A 109.5 . . ? C8 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C8 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 23.97 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.368 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 946299'