# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_publication_text _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name 'Lacour Jerome' _publ_contact_author_address ;Department of Organic Chemistry University of Geneva 30 quai Ernest Ansermet CH-1211 Gen\`eve 4 Switzerland ; _publ_contact_author_email jerome.lacour@unige.ch _publ_contact_author_phone '+41 22 379 60 62' _publ_contact_author_fax '+41 22 379 32 15' loop_ _publ_author_name _publ_author_address A.Sharma ;Department of Organic Chemistry University of Geneva 30 quai Ernest Ansermet CH-1211 Gen\`eve 4 Switzerland ; C.Besnard ;Laboratory of Crystallography University of Geneva 24 quai Ernest Ansermet CH-1211 Gen\`eve 4 Switzerland ; L.Guenee ;Laboratory of Crystallography University of Geneva 24 quai Ernest Ansermet CH-1211 Gen\`eve 4 Switzerland ; J.Lacour ;Department of Organic Chemistry University of Geneva 30 quai Ernest Ansermet CH-1211 Gen\`eve 4 Switzerland ; _publ_section_title ;General asymmetric synthesis of ethano-Tr\"oger bases using CuTC-catalyzed diazo decomposition reactions ; data_5a _database_code_depnum_ccdc_archive 'CCDC 840414' #TrackingRef '- CuTC_EthanoTrogerBases.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H26 N2 O' _chemical_formula_sum 'C26 H26 N2 O' _chemical_formula_weight 382.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.0172(3) _cell_length_b 8.60512(13) _cell_length_c 28.3901(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.4359(17) _cell_angle_gamma 90.00 _cell_volume 4156.01(12) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 12115 _cell_measurement_theta_min 3.1116 _cell_measurement_theta_max 74.0911 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2416 _exptl_crystal_size_mid 0.1364 _exptl_crystal_size_min 0.1012 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 0.578 _exptl_absorpt_correction_T_min 0.901 _exptl_absorpt_correction_T_max 0.952 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_detector_area_resol_mean 10.4679 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 22460 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 74.26 _reflns_number_total 4161 _reflns_number_gt 3666 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material SHELX_Acta _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^)+(0.0663P)^2^+1.5605P] 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 4161 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1174 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.01177(6) 0.55829(11) 0.11237(3) 0.0331(2) Uani 1 1 d . . . N2 N 0.07802(6) 0.70302(12) 0.19195(4) 0.0408(3) Uani 1 1 d . . . C18 C 0.09062(7) 0.54695(15) 0.20769(4) 0.0380(3) Uani 1 1 d . . . C13 C -0.11631(7) 0.68750(13) 0.12206(4) 0.0348(3) Uani 1 1 d . . . C9 C -0.00080(7) 0.42725(13) 0.14443(4) 0.0348(3) Uani 1 1 d . . . H9A H 0.0037 0.3297 0.1262 0.042 Uiso 1 1 calc R . . H9B H -0.0553 0.4332 0.1557 0.042 Uiso 1 1 calc R . . C12 C 0.05457(7) 0.41708(14) 0.18703(4) 0.0352(3) Uani 1 1 d . . . C3 C 0.09113(7) 0.56837(14) 0.09625(4) 0.0370(3) Uani 1 1 d . . . C20 C -0.16435(8) 0.78885(15) 0.14663(5) 0.0426(3) Uani 1 1 d . . . H20 H -0.1410 0.8676 0.1658 0.051 Uiso 1 1 calc R . . C1 C 0.10914(8) 0.47614(17) 0.05777(4) 0.0462(3) Uani 1 1 d . . . H1 H 0.0699 0.4099 0.0444 0.055 Uiso 1 1 calc R . . C10 C -0.02624(7) 0.70263(13) 0.12714(4) 0.0347(3) Uani 1 1 d . . . O22 O 0.00341(7) 0.96609(12) 0.10560(5) 0.0657(3) Uani 1 1 d . . . C19 C -0.15201(8) 0.57689(15) 0.09314(4) 0.0410(3) Uani 1 1 d . . . H19 H -0.1206 0.5083 0.0754 0.049 Uiso 1 1 calc R . . C6 C 0.14961(7) 0.66296(15) 0.11656(5) 0.0413(3) Uani 1 1 d . . . C17 C 0.07011(7) 0.27049(16) 0.20602(5) 0.0443(3) Uani 1 1 d . . . H17 H 0.0453 0.1823 0.1921 0.053 Uiso 1 1 calc R . . C3BA C -0.00209(7) 0.74525(14) 0.17849(4) 0.0393(3) Uani 1 1 d . . . H3BB H -0.0085 0.8587 0.1827 0.047 Uiso 1 1 calc R . . H3BA H -0.0384 0.6929 0.2001 0.047 Uiso 1 1 calc R . . C29 C -0.28024(8) 0.66459(16) 0.11552(5) 0.0473(3) Uani 1 1 d . . . H29 H -0.3359 0.6551 0.1137 0.057 Uiso 1 1 calc R . . C25 C -0.23348(8) 0.56571(16) 0.08997(5) 0.0470(3) Uani 1 1 d . . . H25 H -0.2572 0.4894 0.0701 0.056 Uiso 1 1 calc R . . C24 C 0.14305(8) 0.52535(19) 0.24577(5) 0.0490(3) Uani 1 1 d . . . H24 H 0.1691 0.6126 0.2595 0.059 Uiso 1 1 calc R . . C11 C 0.13805(8) 0.75955(16) 0.16057(5) 0.0470(3) Uani 1 1 d . . . H11B H 0.1887 0.7645 0.1784 0.056 Uiso 1 1 calc R . . H11A H 0.1242 0.8668 0.1509 0.056 Uiso 1 1 calc R . . C26 C -0.24549(8) 0.77698(17) 0.14365(5) 0.0480(3) Uani 1 1 d . . . H26 H -0.2772 0.8463 0.1610 0.058 Uiso 1 1 calc R . . C28 C 0.15757(8) 0.3788(2) 0.26375(5) 0.0569(4) Uani 1 1 d . . . H28 H 0.1935 0.3667 0.2897 0.068 Uiso 1 1 calc R . . C7 C 0.22352(8) 0.66395(17) 0.09606(5) 0.0509(4) Uani 1 1 d . . . H7 H 0.2634 0.7284 0.1096 0.061 Uiso 1 1 calc R . . C21 C -0.00945(10) 0.7976(2) 0.04004(6) 0.0608(4) Uani 1 1 d . . . H21B H 0.0443 0.7931 0.0286 0.091 Uiso 1 1 calc R . . H21C H -0.0389 0.8786 0.0229 0.091 Uiso 1 1 calc R . . H21A H -0.0352 0.6970 0.0349 0.091 Uiso 1 1 calc R . . C14 C -0.00729(7) 0.83501(15) 0.09187(5) 0.0460(3) Uani 1 1 d . . . C2 C 0.18314(9) 0.4790(2) 0.03858(5) 0.0563(4) Uani 1 1 d . . . H2 H 0.1942 0.4141 0.0125 0.068 Uiso 1 1 calc R . . C23 C 0.12061(8) 0.2492(2) 0.24459(5) 0.0546(4) Uani 1 1 d . . . C4 C 0.24128(8) 0.5758(2) 0.05715(5) 0.0569(4) Uani 1 1 d . . . C27 C 0.13410(11) 0.0903(2) 0.26534(8) 0.0842(7) Uani 1 1 d . . . H27C H 0.1066 0.0820 0.2951 0.126 Uiso 1 1 calc R . . H27B H 0.1905 0.0742 0.2711 0.126 Uiso 1 1 calc R . . H27A H 0.1140 0.0113 0.2433 0.126 Uiso 1 1 calc R . . C8 C 0.32209(10) 0.5840(3) 0.03630(7) 0.0835(7) Uani 1 1 d . . . H8A H 0.3314 0.4902 0.0177 0.125 Uiso 1 1 calc R . . H8C H 0.3619 0.5914 0.0617 0.125 Uiso 1 1 calc R . . H8B H 0.3253 0.6757 0.0160 0.125 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0312(5) 0.0351(5) 0.0332(5) 0.0025(4) 0.0048(4) 0.0038(4) N2 0.0334(5) 0.0431(6) 0.0457(6) -0.0071(4) -0.0009(4) 0.0023(4) C18 0.0304(6) 0.0506(7) 0.0333(6) -0.0010(5) 0.0044(5) 0.0069(5) C13 0.0321(6) 0.0365(6) 0.0359(6) 0.0075(4) 0.0035(4) 0.0032(4) C9 0.0344(6) 0.0346(6) 0.0357(6) 0.0010(4) 0.0026(5) 0.0006(4) C12 0.0285(5) 0.0434(6) 0.0339(6) 0.0051(5) 0.0072(4) 0.0048(4) C3 0.0332(6) 0.0417(6) 0.0364(6) 0.0090(5) 0.0054(5) 0.0075(5) C20 0.0366(6) 0.0416(6) 0.0499(7) -0.0003(5) 0.0048(5) 0.0056(5) C1 0.0439(7) 0.0586(8) 0.0365(6) 0.0052(6) 0.0065(5) 0.0134(6) C10 0.0316(6) 0.0337(6) 0.0391(6) 0.0028(4) 0.0051(5) 0.0037(4) O22 0.0615(7) 0.0408(6) 0.0946(9) 0.0161(5) -0.0029(6) -0.0043(5) C19 0.0381(6) 0.0457(7) 0.0391(6) 0.0017(5) 0.0002(5) 0.0037(5) C6 0.0333(6) 0.0419(6) 0.0489(7) 0.0121(5) 0.0038(5) 0.0040(5) C17 0.0306(6) 0.0509(7) 0.0519(7) 0.0156(6) 0.0108(5) 0.0065(5) C3BA 0.0342(6) 0.0383(6) 0.0455(7) -0.0064(5) 0.0019(5) 0.0044(5) C29 0.0320(6) 0.0529(7) 0.0572(8) 0.0178(6) 0.0032(5) 0.0005(5) C25 0.0409(7) 0.0496(7) 0.0502(7) 0.0071(6) -0.0059(6) -0.0035(6) C24 0.0340(6) 0.0755(10) 0.0375(7) -0.0047(6) 0.0004(5) 0.0089(6) C11 0.0335(6) 0.0436(7) 0.0640(8) -0.0008(6) -0.0009(6) -0.0039(5) C26 0.0368(7) 0.0512(7) 0.0564(8) 0.0081(6) 0.0107(6) 0.0099(6) C28 0.0342(7) 0.0967(12) 0.0399(7) 0.0172(7) 0.0025(5) 0.0171(7) C7 0.0342(7) 0.0567(8) 0.0620(9) 0.0236(7) 0.0054(6) 0.0054(6) C21 0.0571(9) 0.0707(10) 0.0552(9) 0.0304(7) 0.0173(7) 0.0159(7) C14 0.0317(6) 0.0440(7) 0.0626(8) 0.0155(6) 0.0065(6) 0.0038(5) C2 0.0497(8) 0.0808(10) 0.0391(7) 0.0112(7) 0.0124(6) 0.0250(8) C23 0.0331(7) 0.0744(10) 0.0568(8) 0.0295(8) 0.0105(6) 0.0128(7) C4 0.0384(7) 0.0808(11) 0.0521(8) 0.0289(7) 0.0134(6) 0.0199(7) C27 0.0533(10) 0.0951(14) 0.1041(15) 0.0609(12) 0.0030(9) 0.0137(9) C8 0.0428(9) 0.1341(19) 0.0747(12) 0.0344(12) 0.0215(8) 0.0241(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.4394(15) . ? N1 C10 1.4664(14) . ? N1 C9 1.4681(14) . ? N2 C18 1.4299(16) . ? N2 C3BA 1.4526(15) . ? N2 C11 1.4560(17) . ? C18 C24 1.3967(17) . ? C18 C12 1.3968(18) . ? C13 C19 1.3871(18) . ? C13 C20 1.3943(17) . ? C13 C10 1.5415(16) . ? C9 C12 1.5170(16) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C12 C17 1.3945(17) . ? C3 C1 1.3907(18) . ? C3 C6 1.3989(19) . ? C20 C26 1.3850(18) . ? C20 H20 0.9500 . ? C1 C2 1.3847(19) . ? C1 H1 0.9500 . ? C10 C3BA 1.5489(17) . ? C10 C14 1.5558(16) . ? O22 C14 1.2057(18) . ? C19 C25 1.3904(18) . ? C19 H19 0.9500 . ? C6 C7 1.3990(18) . ? C6 C11 1.5175(19) . ? C17 C23 1.387(2) . ? C17 H17 0.9500 . ? C3BA H3BB 0.9900 . ? C3BA H3BA 0.9900 . ? C29 C26 1.378(2) . ? C29 C25 1.383(2) . ? C29 H29 0.9500 . ? C25 H25 0.9500 . ? C24 C28 1.380(2) . ? C24 H24 0.9500 . ? C11 H11B 0.9900 . ? C11 H11A 0.9900 . ? C26 H26 0.9500 . ? C28 C23 1.385(2) . ? C28 H28 0.9500 . ? C7 C4 1.380(2) . ? C7 H7 0.9500 . ? C21 C14 1.506(2) . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C21 H21A 0.9800 . ? C2 C4 1.387(3) . ? C2 H2 0.9500 . ? C23 C27 1.503(2) . ? C4 C8 1.5123(19) . ? C27 H27C 0.9800 . ? C27 H27B 0.9800 . ? C27 H27A 0.9800 . ? C8 H8A 0.9800 . ? C8 H8C 0.9800 . ? C8 H8B 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C10 117.64(9) . . ? C3 N1 C9 113.32(9) . . ? C10 N1 C9 113.65(9) . . ? C18 N2 C3BA 116.71(10) . . ? C18 N2 C11 113.77(10) . . ? C3BA N2 C11 115.06(11) . . ? C24 C18 C12 118.94(12) . . ? C24 C18 N2 117.05(12) . . ? C12 C18 N2 124.01(11) . . ? C19 C13 C20 118.15(12) . . ? C19 C13 C10 122.22(11) . . ? C20 C13 C10 119.63(11) . . ? N1 C9 C12 116.19(9) . . ? N1 C9 H9A 108.2 . . ? C12 C9 H9A 108.2 . . ? N1 C9 H9B 108.2 . . ? C12 C9 H9B 108.2 . . ? H9A C9 H9B 107.4 . . ? C17 C12 C18 118.97(12) . . ? C17 C12 C9 117.93(11) . . ? C18 C12 C9 123.10(10) . . ? C1 C3 C6 119.17(12) . . ? C1 C3 N1 116.26(11) . . ? C6 C3 N1 124.57(11) . . ? C26 C20 C13 121.29(13) . . ? C26 C20 H20 119.4 . . ? C13 C20 H20 119.4 . . ? C2 C1 C3 121.29(14) . . ? C2 C1 H1 119.4 . . ? C3 C1 H1 119.4 . . ? N1 C10 C13 110.26(9) . . ? N1 C10 C3BA 111.17(9) . . ? C13 C10 C3BA 110.35(9) . . ? N1 C10 C14 109.65(10) . . ? C13 C10 C14 102.90(9) . . ? C3BA C10 C14 112.22(10) . . ? C13 C19 C25 120.47(12) . . ? C13 C19 H19 119.8 . . ? C25 C19 H19 119.8 . . ? C3 C6 C7 118.02(13) . . ? C3 C6 C11 123.54(11) . . ? C7 C6 C11 118.40(12) . . ? C23 C17 C12 122.19(14) . . ? C23 C17 H17 118.9 . . ? C12 C17 H17 118.9 . . ? N2 C3BA C10 114.42(10) . . ? N2 C3BA H3BB 108.7 . . ? C10 C3BA H3BB 108.7 . . ? N2 C3BA H3BA 108.7 . . ? C10 C3BA H3BA 108.7 . . ? H3BB C3BA H3BA 107.6 . . ? C26 C29 C25 119.44(12) . . ? C26 C29 H29 120.3 . . ? C25 C29 H29 120.3 . . ? C29 C25 C19 120.62(13) . . ? C29 C25 H25 119.7 . . ? C19 C25 H25 119.7 . . ? C28 C24 C18 120.85(14) . . ? C28 C24 H24 119.6 . . ? C18 C24 H24 119.6 . . ? N2 C11 C6 115.36(10) . . ? N2 C11 H11B 108.4 . . ? C6 C11 H11B 108.4 . . ? N2 C11 H11A 108.4 . . ? C6 C11 H11A 108.4 . . ? H11B C11 H11A 107.5 . . ? C29 C26 C20 119.99(13) . . ? C29 C26 H26 120.0 . . ? C20 C26 H26 120.0 . . ? C24 C28 C23 121.02(13) . . ? C24 C28 H28 119.5 . . ? C23 C28 H28 119.5 . . ? C4 C7 C6 123.16(15) . . ? C4 C7 H7 118.4 . . ? C6 C7 H7 118.4 . . ? C14 C21 H21B 109.5 . . ? C14 C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C14 C21 H21A 109.5 . . ? H21B C21 H21A 109.5 . . ? H21C C21 H21A 109.5 . . ? O22 C14 C21 121.03(13) . . ? O22 C14 C10 120.60(13) . . ? C21 C14 C10 118.18(12) . . ? C1 C2 C4 120.54(14) . . ? C1 C2 H2 119.7 . . ? C4 C2 H2 119.7 . . ? C28 C23 C17 117.99(13) . . ? C28 C23 C27 121.00(15) . . ? C17 C23 C27 121.00(17) . . ? C7 C4 C2 117.77(13) . . ? C7 C4 C8 120.47(17) . . ? C2 C4 C8 121.75(16) . . ? C23 C27 H27C 109.5 . . ? C23 C27 H27B 109.5 . . ? H27C C27 H27B 109.5 . . ? C23 C27 H27A 109.5 . . ? H27C C27 H27A 109.5 . . ? H27B C27 H27A 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? H8C C8 H8B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 74.26 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.197 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.034 #### END ##### data_5c _database_code_depnum_ccdc_archive 'CCDC 840415' #TrackingRef '- CuTC_EthanoTrogerBases.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; # End of 'script/refcif.dat' #end of refcif _cell_length_a 17.051(2) _cell_length_b 7.5405(6) _cell_length_c 28.226(4) _cell_angle_alpha 90 _cell_angle_beta 93.201(10) _cell_angle_gamma 90 _cell_volume 3623.3(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' _symmetry_space_group_name_Hall '-C 2yc' 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 -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C24 H1.25 N2 O3 # Dc = 1.34 Fooo = 1552.00 Mu = 0.91 M = 365.54 # Found Formula = C22 H24 N2 O3 # Dc = 1.34 FOOO = 1552.00 Mu = 0.89 M = 364.44 _chemical_formula_sum 'C22 H24 N2 O3' _chemical_formula_moiety 'C22 H24 N2 O3' _chemical_compound_source ? _chemical_formula_weight 364.44 _cell_measurement_reflns_used 15643 _cell_measurement_theta_min 1 _cell_measurement_theta_max 29 _cell_measurement_temperature 220 _exptl_crystal_description platelet _exptl_crystal_colour orange _exptl_crystal_size_min 0.050 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_max 0.500 _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.089 # Sheldrick geometric approximatio 0.96 1.00 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'IPDS (Stoe & Cie, 1996)' _computing_cell_refinement 'IPDS (Stoe & Cie, 1996)' _computing_data_reduction 'XRED (Stoe & Cie 1996)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 220 _diffrn_reflns_number 11824 _reflns_number_total 3385 _diffrn_reflns_av_R_equivalents 0.051 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 3385 # Theoretical number of reflections is about 6863 _diffrn_reflns_theta_min 1.445 _diffrn_reflns_theta_max 25.657 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.143 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _reflns_limit_h_min -20 _reflns_limit_h_max 20 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 34 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.28 _refine_diff_density_max 0.34 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 3373 _refine_ls_number_restraints 0 _refine_ls_number_parameters 244 _oxford_refine_ls_R_factor_ref 0.0721 _refine_ls_wR_factor_ref 0.1015 _refine_ls_goodness_of_fit_ref 1.1573 _refine_ls_shift/su_max 0.0002460 _refine_ls_shift/su_mean 0.0000379 # The values computed from all data _oxford_reflns_number_all 3373 _refine_ls_R_factor_all 0.0721 _refine_ls_wR_factor_all 0.1015 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3013 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_gt 0.1011 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 18.2 21.2 6.66 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Stoe & Cie (1996). IPDS Software. Stoe & Cie (1996). XRED V1.08. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O 1.14332(10) 0.2791(3) 0.64007(7) 0.0466 1.0000 Uani . . . . . . . C2 C 1.22673(15) 0.2605(5) 0.64186(11) 0.0522 1.0000 Uani . . . . . . . C5 C 1.10250(16) 0.1427(4) 0.62352(10) 0.0409 1.0000 Uani . . . . . . . O6 O 1.13088(12) 0.0103(3) 0.61057(9) 0.0623 1.0000 Uani . . . . . . . C7 C 1.01535(14) 0.1842(4) 0.62343(9) 0.0342 1.0000 Uani . . . . . . . N8 N 0.97061(12) 0.0278(3) 0.61283(7) 0.0347 1.0000 Uani . . . . . . . C9 C 0.89337(15) 0.0518(4) 0.59406(9) 0.0362 1.0000 Uani . . . . . . . C10 C 0.86934(17) -0.0586(4) 0.55722(10) 0.0488 1.0000 Uani . . . . . . . C11 C 0.79652(19) -0.0423(5) 0.53537(10) 0.0563 1.0000 Uani . . . . . . . C12 C 0.74532(18) 0.0829(5) 0.54925(11) 0.0525 1.0000 Uani . . . . . . . C13 C 0.66529(19) 0.1032(6) 0.52591(12) 0.0772 1.0000 Uani . . . . . . . C14 C 0.76822(16) 0.1901(4) 0.58642(10) 0.0456 1.0000 Uani . . . . . . . C15 C 0.84158(15) 0.1768(4) 0.60928(9) 0.0363 1.0000 Uani . . . . . . . C16 C 0.85982(15) 0.2967(4) 0.65042(9) 0.0380 1.0000 Uani . . . . . . . N17 N 0.91867(12) 0.2358(3) 0.68420(7) 0.0337 1.0000 Uani . . . . . . . C18 C 0.99756(14) 0.2645(4) 0.67157(9) 0.0369 1.0000 Uani . . . . . . . C19 C 0.97875(16) -0.1102(4) 0.64807(10) 0.0409 1.0000 Uani . . . . . . . C20 C 0.93033(15) -0.0888(4) 0.69046(9) 0.0355 1.0000 Uani . . . . . . . C21 C 0.90231(15) 0.0711(4) 0.70538(9) 0.0345 1.0000 Uani . . . . . . . C22 C 0.85477(15) 0.0734(4) 0.74294(9) 0.0401 1.0000 Uani . . . . . . . C23 C 0.83884(16) -0.0781(4) 0.76670(10) 0.0436 1.0000 Uani . . . . . . . C24 C 0.86921(16) -0.2372(4) 0.75402(10) 0.0426 1.0000 Uani . . . . . . . C25 C 0.91398(15) -0.2398(4) 0.71565(10) 0.0414 1.0000 Uani . . . . . . . C26 C 0.85589(18) -0.4008(4) 0.78138(12) 0.0589 1.0000 Uani . . . . . . . O4 O 0.98755(13) 0.4670(3) 0.58922(8) 0.0527 1.0000 Uani . . . . . . . C27 C 1.00276(16) 0.3164(4) 0.58255(10) 0.0415 1.0000 Uani . . . . . . . C28 C 1.01447(18) 0.2444(5) 0.53474(10) 0.0510 1.0000 Uani . . . . . . . H182 H 1.0330 0.2106 0.6963 0.0448 1.0000 Uiso R . . . . . . H181 H 1.0086 0.3916 0.6704 0.0449 1.0000 Uiso R . . . . . . H221 H 0.8328 0.1841 0.7519 0.0477 1.0000 Uiso R . . . . . . H162 H 0.8766 0.4118 0.6384 0.0456 1.0000 Uiso R . . . . . . H161 H 0.8119 0.3102 0.6664 0.0449 1.0000 Uiso R . . . . . . H101 H 0.9042 -0.1452 0.5468 0.0583 1.0000 Uiso R . . . . . . H111 H 0.7814 -0.1187 0.5102 0.0669 1.0000 Uiso R . . . . . . H141 H 0.7332 0.2790 0.5965 0.0544 1.0000 Uiso R . . . . . . H231 H 0.8080 -0.0723 0.7931 0.0532 1.0000 Uiso R . . . . . . H192 H 1.0328 -0.1161 0.6596 0.0488 1.0000 Uiso R . . . . . . H191 H 0.9618 -0.2267 0.6327 0.0481 1.0000 Uiso R . . . . . . H251 H 0.9340 -0.3509 0.7059 0.0495 1.0000 Uiso R . . . . . . H283 H 1.0558 0.1601 0.5360 0.0777 1.0000 Uiso R . . . . . . H282 H 1.0250 0.3383 0.5152 0.0782 1.0000 Uiso R . . . . . . H281 H 0.9661 0.1862 0.5242 0.0778 1.0000 Uiso R . . . . . . H263 H 0.8805 -0.5025 0.7677 0.0893 1.0000 Uiso R . . . . . . H262 H 0.8792 -0.3927 0.8124 0.0890 1.0000 Uiso R . . . . . . H261 H 0.8009 -0.4290 0.7826 0.0893 1.0000 Uiso R . . . . . . H133 H 0.6545 0.2224 0.5157 0.1165 1.0000 Uiso R . . . . . . H131 H 0.6245 0.0666 0.5462 0.1163 1.0000 Uiso R . . . . . . H132 H 0.6596 0.0267 0.4982 0.1165 1.0000 Uiso R . . . . . . H23 H 1.2502 0.3734 0.6488 0.0787 1.0000 Uiso R . . . . . . H22 H 1.2416 0.1749 0.6648 0.0786 1.0000 Uiso R . . . . . . H21 H 1.2404 0.2184 0.6122 0.0780 1.0000 Uiso 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 0.0297(10) 0.0469(13) 0.0641(13) -0.0075(11) 0.0101(9) -0.0044(9) C2 0.0283(14) 0.063(2) 0.065(2) 0.0073(18) 0.0068(13) -0.0030(15) C5 0.0374(15) 0.0456(18) 0.0405(16) -0.0031(14) 0.0088(12) 0.0000(14) O6 0.0405(12) 0.0552(15) 0.0927(18) -0.0258(13) 0.0169(12) 0.0057(11) C7 0.0301(13) 0.0356(15) 0.0373(14) -0.0075(12) 0.0060(11) 0.0003(12) N8 0.0341(12) 0.0326(13) 0.0379(12) -0.0078(10) 0.006(1) -0.0006(10) C9 0.0355(14) 0.0374(16) 0.0362(14) -0.0022(13) 0.0065(11) -0.0078(12) C10 0.0520(18) 0.051(2) 0.0443(17) -0.0110(15) 0.0123(14) -0.0149(16) C11 0.060(2) 0.067(2) 0.0408(17) -0.0043(17) -0.0008(15) -0.0348(19) C12 0.0425(17) 0.064(2) 0.0508(18) 0.0147(17) -0.0026(14) -0.0209(17) C13 0.056(2) 0.101(3) 0.072(2) 0.027(2) -0.0197(18) -0.032(2) C14 0.0375(15) 0.0507(19) 0.0489(17) 0.0119(15) 0.0047(13) -0.0065(14) C15 0.0346(14) 0.0364(16) 0.0383(15) 0.0023(12) 0.0053(11) -0.0054(12) C16 0.0339(14) 0.0361(16) 0.0445(16) -0.0010(13) 0.0072(12) 0.0046(12) N17 0.0305(11) 0.0314(12) 0.0396(12) -0.0062(10) 0.0061(9) 0.0000(10) C18 0.0336(14) 0.0359(15) 0.0417(15) -0.0109(13) 0.0066(11) -0.0028(12) C19 0.0397(15) 0.0345(16) 0.0491(17) -0.0061(14) 0.0072(13) 0.0061(13) C20 0.0299(13) 0.0355(15) 0.0411(15) -0.0030(13) 0.0028(11) 0.0025(12) C21 0.0308(13) 0.0367(15) 0.0362(14) -0.0031(12) 0.0024(11) 0.0008(12) C22 0.0368(15) 0.0427(17) 0.0416(16) -0.0064(14) 0.0087(12) -0.0006(13) C23 0.0384(15) 0.0505(19) 0.0424(16) 0.0024(15) 0.0057(13) -0.0045(14) C24 0.0349(15) 0.0450(17) 0.0474(17) 0.0062(15) -0.0027(12) -0.0056(14) C25 0.0350(14) 0.0351(16) 0.0536(18) -0.0003(14) -0.0017(13) 0.0039(13) C26 0.0498(19) 0.055(2) 0.072(2) 0.0215(19) 0.0023(16) -0.0046(17) O4 0.0617(14) 0.0387(13) 0.0590(13) 0.0033(11) 0.0150(11) 0.0053(11) C27 0.0320(15) 0.0447(18) 0.0485(17) -0.0060(14) 0.0073(12) -0.0038(13) C28 0.0555(18) 0.059(2) 0.0394(16) 0.0004(16) 0.0115(14) -0.0044(17) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4684(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.427(3) yes O1 . C5 . 1.313(3) yes C2 . H23 . 0.956 no C2 . H22 . 0.940 no C2 . H21 . 0.937 no C5 . O6 . 1.176(3) yes C5 . C7 . 1.518(4) yes C7 . N8 . 1.427(3) yes C7 . C18 . 1.534(3) yes C7 . C27 . 1.531(4) yes N8 . C9 . 1.404(3) yes N8 . C19 . 1.441(3) yes C9 . C10 . 1.377(4) yes C9 . C15 . 1.376(4) yes C10 . C11 . 1.361(4) yes C10 . H101 . 0.941 no C11 . C12 . 1.358(5) yes C11 . H111 . 0.939 no C12 . C13 . 1.489(4) yes C12 . C14 . 1.364(4) yes C13 . H133 . 0.959 no C13 . H131 . 0.965 no C13 . H132 . 0.973 no C14 . C15 . 1.379(4) yes C14 . H141 . 0.952 no C15 . C16 . 1.491(4) yes C16 . N17 . 1.421(3) yes C16 . H162 . 0.980 no C16 . H161 . 0.962 no N17 . C18 . 1.427(3) yes N17 . C21 . 1.413(3) yes C18 . H182 . 0.985 no C18 . H181 . 0.978 no C19 . C20 . 1.500(3) yes C19 . H192 . 0.961 no C19 . H191 . 1.015 no C20 . C21 . 1.371(4) yes C20 . C25 . 1.379(4) yes C21 . C22 . 1.370(3) yes C22 . C23 . 1.360(4) yes C22 . H221 . 0.955 no C23 . C24 . 1.362(4) yes C23 . H231 . 0.938 no C24 . C25 . 1.360(4) yes C24 . C26 . 1.480(4) yes C25 . H251 . 0.952 no C26 . H263 . 0.965 no C26 . H262 . 0.942 no C26 . H261 . 0.964 no O4 . C27 . 1.182(3) yes C27 . C28 . 1.479(4) yes C28 . H283 . 0.949 no C28 . H282 . 0.921 no C28 . H281 . 0.966 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C5 . 116.3(2) yes O1 . C2 . H23 . 108.9 no O1 . C2 . H22 . 108.8 no H23 . C2 . H22 . 112.2 no O1 . C2 . H21 . 107.4 no H23 . C2 . H21 . 111.3 no H22 . C2 . H21 . 108.2 no O1 . C5 . O6 . 123.8(3) yes O1 . C5 . C7 . 109.8(2) yes O6 . C5 . C7 . 126.4(3) yes C5 . C7 . N8 . 110.0(2) yes C5 . C7 . C18 . 108.8(2) yes N8 . C7 . C18 . 112.5(2) yes C5 . C7 . C27 . 103.4(2) yes N8 . C7 . C27 . 109.2(2) yes C18 . C7 . C27 . 112.6(2) yes C7 . N8 . C9 . 116.9(2) yes C7 . N8 . C19 . 115.0(2) yes C9 . N8 . C19 . 113.9(2) yes N8 . C9 . C10 . 116.1(3) yes N8 . C9 . C15 . 125.1(2) yes C10 . C9 . C15 . 118.7(3) yes C9 . C10 . C11 . 120.9(3) yes C9 . C10 . H101 . 119.2 no C11 . C10 . H101 . 119.9 no C10 . C11 . C12 . 121.1(3) yes C10 . C11 . H111 . 119.5 no C12 . C11 . H111 . 119.4 no C11 . C12 . C13 . 122.1(3) yes C11 . C12 . C14 . 118.2(3) yes C13 . C12 . C14 . 119.7(3) yes C12 . C13 . H133 . 112.7 no C12 . C13 . H131 . 112.4 no H133 . C13 . H131 . 108.3 no C12 . C13 . H132 . 110.0 no H133 . C13 . H132 . 107.7 no H131 . C13 . H132 . 105.4 no C12 . C14 . C15 . 122.0(3) yes C12 . C14 . H141 . 119.3 no C15 . C14 . H141 . 118.7 no C14 . C15 . C9 . 119.0(3) yes C14 . C15 . C16 . 117.7(3) yes C9 . C15 . C16 . 123.3(2) yes C15 . C16 . N17 . 115.8(2) yes C15 . C16 . H162 . 108.7 no N17 . C16 . H162 . 108.0 no C15 . C16 . H161 . 106.5 no N17 . C16 . H161 . 107.8 no H162 . C16 . H161 . 110.0 no C16 . N17 . C18 . 115.0(2) yes C16 . N17 . C21 . 114.8(2) yes C18 . N17 . C21 . 116.8(2) yes C7 . C18 . N17 . 113.4(2) yes C7 . C18 . H182 . 108.7 no N17 . C18 . H182 . 108.1 no C7 . C18 . H181 . 108.0 no N17 . C18 . H181 . 110.1 no H182 . C18 . H181 . 108.5 no N8 . C19 . C20 . 115.9(2) yes N8 . C19 . H192 . 108.8 no C20 . C19 . H192 . 107.1 no N8 . C19 . H191 . 108.5 no C20 . C19 . H191 . 106.1 no H192 . C19 . H191 . 110.5 no C19 . C20 . C21 . 123.8(3) yes C19 . C20 . C25 . 117.3(2) yes C21 . C20 . C25 . 118.9(2) yes N17 . C21 . C20 . 124.2(2) yes N17 . C21 . C22 . 117.1(2) yes C20 . C21 . C22 . 118.7(3) yes C21 . C22 . C23 . 120.9(3) yes C21 . C22 . H221 . 118.3 no C23 . C22 . H221 . 120.8 no C22 . C23 . C24 . 121.4(3) yes C22 . C23 . H231 . 119.4 no C24 . C23 . H231 . 119.2 no C23 . C24 . C25 . 117.4(3) yes C23 . C24 . C26 . 121.7(3) yes C25 . C24 . C26 . 120.8(3) yes C20 . C25 . C24 . 122.5(3) yes C20 . C25 . H251 . 119.5 no C24 . C25 . H251 . 118.1 no C24 . C26 . H263 . 111.8 no C24 . C26 . H262 . 111.2 no H263 . C26 . H262 . 104.7 no C24 . C26 . H261 . 112.4 no H263 . C26 . H261 . 106.5 no H262 . C26 . H261 . 109.9 no C7 . C27 . O4 . 121.9(3) yes C7 . C27 . C28 . 115.3(3) yes O4 . C27 . C28 . 122.7(3) yes C27 . C28 . H283 . 110.4 no C27 . C28 . H282 . 107.8 no H283 . C28 . H282 . 111.6 no C27 . C28 . H281 . 106.9 no H283 . C28 . H281 . 109.1 no H282 . C28 . H281 . 111.0 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C16 . H162 . O4 . 127 0.98 2.44 3.130(4) yes C14 . H141 . O6 3_455 171 0.95 2.51 3.458(4) yes ##### END ###### data_5i _database_code_depnum_ccdc_archive 'CCDC 840416' #TrackingRef '- CuTC_EthanoTrogerBases.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; # End of 'script/refcif.dat' #end of refcif _cell_length_a 14.113(6) _cell_length_b 14.919(5) _cell_length_c 19.801(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4169(2) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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 x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C24 H18 N2 O0.25 # Dc = 1.08 Fooo = 1680.00 Mu = 0.64 M = 338.42 # Found Formula = C24 H28 N2 O3 # Dc = 1.25 FOOO = 1680.00 Mu = 0.83 M = 392.50 _chemical_formula_sum 'C24 H28 N2 O3' _chemical_formula_moiety 'C24 H28 N2 O3' _chemical_compound_source ? _chemical_formula_weight 392.50 _cell_measurement_reflns_used 25096 _cell_measurement_theta_min 5 _cell_measurement_theta_max 26 _cell_measurement_temperature 200 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_max 0.400 _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.083 # Sheldrick geometric approximatio 0.97 0.99 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'IPDS (Stoe & Cie, 1996)' _computing_cell_refinement 'IPDS (Stoe & Cie, 1996)' _computing_data_reduction 'XRED (Stoe & Cie 1996)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 29403 _reflns_number_total 4240 _diffrn_reflns_av_R_equivalents 0.031 # Number of reflections without Friedels Law is 11007 # Number of reflections with Friedels Law is 4240 # Theoretical number of reflections is about 4267 _diffrn_reflns_theta_min 4.943 _diffrn_reflns_theta_max 26.380 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.852 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min 0 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.26 _refine_diff_density_max 0.31 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 4237 _refine_ls_number_restraints 0 _refine_ls_number_parameters 262 _oxford_refine_ls_R_factor_ref 0.0576 _refine_ls_wR_factor_ref 0.1193 _refine_ls_goodness_of_fit_ref 0.9975 _refine_ls_shift/su_max 0.0022807 _refine_ls_shift/su_mean 0.0005391 # The values computed from all data _oxford_reflns_number_all 4237 _refine_ls_R_factor_all 0.0576 _refine_ls_wR_factor_all 0.1193 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4110 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_gt 0.1189 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.72 2.10 0.462 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Stoe & Cie (1996). IPDS Software. Stoe & Cie (1996). XRED V1.08. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O 0.62608(8) 0.79323(7) 0.39101(7) 0.0435 1.0000 Uani . . . . . . . C2 C 0.65039(13) 0.88851(10) 0.40144(9) 0.0439 1.0000 Uani . . . . . . . C3 C 0.68007(15) 0.92703(13) 0.33500(11) 0.0547 1.0000 Uani . . . . . . . H33 H 0.7036 0.9880 0.3396 0.0815 1.0000 Uiso R . . . . . . H32 H 0.7290 0.8892 0.3149 0.0814 1.0000 Uiso R . . . . . . H31 H 0.6262 0.9272 0.3025 0.0824 1.0000 Uiso R . . . . . . C4 C 0.7283(2) 0.88978(14) 0.45334(12) 0.0763 1.0000 Uani . . . . . . . H43 H 0.7471 0.9494 0.4619 0.1144 1.0000 Uiso R . . . . . . H42 H 0.7084 0.8630 0.4943 0.1159 1.0000 Uiso R . . . . . . H41 H 0.7840 0.8572 0.4362 0.1154 1.0000 Uiso R . . . . . . H21 H 0.5919 0.9183 0.4180 0.0520 1.0000 Uiso R . . . . . . C5 C 0.53624(11) 0.77475(10) 0.37276(8) 0.0363 1.0000 Uani . . . . . . . O6 O 0.47307(9) 0.82821(8) 0.37097(7) 0.0481 1.0000 Uani . . . . . . . C7 C 0.53111(10) 0.67476(10) 0.35313(8) 0.0335 1.0000 Uani . . . . . . . N8 N 0.43497(8) 0.65185(8) 0.33164(6) 0.0296 1.0000 Uani . . . . . . . C9 C 0.40199(10) 0.69512(10) 0.26961(8) 0.0317 1.0000 Uani . . . . . . . C10 C 0.43719(11) 0.65674(10) 0.20288(8) 0.0341 1.0000 Uani . . . . . . . C11 C 0.38238(12) 0.67405(11) 0.14518(8) 0.0399 1.0000 Uani . . . . . . . C12 C 0.40584(14) 0.64050(12) 0.08192(9) 0.0474 1.0000 Uani . . . . . . . C13 C 0.34254(18) 0.65556(16) 0.02132(10) 0.0655 1.0000 Uani . . . . . . . H131 H 0.3784 0.6507 -0.0207 0.1012 1.0000 Uiso R . . . . . . H133 H 0.3132 0.7145 0.0227 0.1012 1.0000 Uiso R . . . . . . H132 H 0.2933 0.6120 0.0185 0.1000 1.0000 Uiso R . . . . . . C14 C 0.48741(15) 0.58897(13) 0.07708(9) 0.0557 1.0000 Uani . . . . . . . C15 C 0.54227(13) 0.57134(12) 0.13248(10) 0.0506 1.0000 Uani . . . . . . . C16 C 0.51885(11) 0.60510(10) 0.19689(8) 0.0378 1.0000 Uani . . . . . . . N17 N 0.58157(9) 0.58529(9) 0.25138(8) 0.0402 1.0000 Uani . . . . . . . C18 C 0.60558(11) 0.65836(11) 0.29653(9) 0.0413 1.0000 Uani . . . . . . . H181 H 0.6634 0.6442 0.3200 0.0500 1.0000 Uiso R . . . . . . H182 H 0.6121 0.7146 0.2700 0.0494 1.0000 Uiso R . . . . . . C19 C 0.56563(11) 0.49933(11) 0.28471(10) 0.0437 1.0000 Uani . . . . . . . C20 C 0.47025(10) 0.48741(10) 0.31979(8) 0.0333 1.0000 Uani . . . . . . . C21 C 0.40982(10) 0.55825(9) 0.33682(7) 0.0300 1.0000 Uani . . . . . . . C22 C 0.31949(11) 0.53945(10) 0.36139(9) 0.0379 1.0000 Uani . . . . . . . C23 C 0.29063(12) 0.45236(11) 0.37242(9) 0.0437 1.0000 Uani . . . . . . . C24 C 0.35177(12) 0.38067(10) 0.36078(8) 0.0368 1.0000 Uani . . . . . . . C25 C 0.44001(11) 0.39954(10) 0.33398(8) 0.0363 1.0000 Uani . . . . . . . H251 H 0.4834 0.3526 0.3267 0.0451 1.0000 Uiso R . . . . . . C26 C 0.32108(16) 0.28627(11) 0.37747(10) 0.0554 1.0000 Uani . . . . . . . H261 H 0.3601 0.2411 0.3565 0.0842 1.0000 Uiso R . . . . . . H263 H 0.3248 0.2743 0.4257 0.0865 1.0000 Uiso R . . . . . . H262 H 0.2569 0.2759 0.3669 0.0865 1.0000 Uiso R . . . . . . H231 H 0.2281 0.4384 0.3883 0.0531 1.0000 Uiso R . . . . . . H221 H 0.2775 0.5871 0.3721 0.0465 1.0000 Uiso R . . . . . . H192 H 0.6154 0.4879 0.3172 0.0519 1.0000 Uiso R . . . . . . H191 H 0.5709 0.4513 0.2480 0.0516 1.0000 Uiso R . . . . . . H151 H 0.5950 0.5365 0.1323 0.0598 1.0000 Uiso R . . . . . . H141 H 0.5038 0.5660 0.0356 0.0685 1.0000 Uiso R . . . . . . H111 H 0.3254 0.7114 0.1494 0.0493 1.0000 Uiso R . . . . . . H92 H 0.4181 0.7583 0.2730 0.0386 1.0000 Uiso R . . . . . . H91 H 0.3331 0.6885 0.2676 0.0397 1.0000 Uiso R . . . . . . C27 C 0.55321(13) 0.62368(10) 0.42001(9) 0.0444 1.0000 Uani . . . . . . . O28 O 0.62684(10) 0.58238(9) 0.42586(9) 0.0640 1.0000 Uani . . . . . . . C29 C 0.48370(17) 0.63217(14) 0.47598(10) 0.0604 1.0000 Uani . . . . . . . H292 H 0.4313 0.6671 0.4649 0.0903 1.0000 Uiso R . . . . . . H291 H 0.5141 0.6581 0.5117 0.0937 1.0000 Uiso R . . . . . . H293 H 0.4618 0.5737 0.4889 0.0931 1.0000 Uiso 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 0.0441(6) 0.0237(5) 0.0627(7) -0.0056(5) -0.0133(5) -0.0038(4) C2 0.0524(10) 0.0236(7) 0.0556(10) -0.0041(6) -0.0099(8) -0.0053(7) C3 0.0607(11) 0.0406(9) 0.0628(11) 0.0028(8) -0.0024(9) -0.0060(8) C4 0.1076(19) 0.0409(10) 0.0804(15) 0.0026(10) -0.0504(14) -0.0229(11) C5 0.0394(8) 0.0272(7) 0.0424(8) -0.0042(6) -0.0021(6) -0.0003(6) O6 0.0452(7) 0.0320(6) 0.0671(8) -0.0124(5) -0.0027(6) 0.0065(5) C7 0.0309(7) 0.0255(7) 0.0440(8) -0.0059(6) -0.0038(6) 0.0006(5) N8 0.0280(6) 0.0255(6) 0.0354(6) -0.0023(5) 0.0008(5) 0.0015(4) C9 0.0295(7) 0.0284(7) 0.0371(7) -0.0007(5) 0.0034(5) 0.0033(5) C10 0.0346(7) 0.0293(7) 0.0384(7) -0.0044(6) 0.0076(6) -0.0100(6) C11 0.0455(9) 0.0368(8) 0.0375(8) -0.0006(6) 0.0072(7) -0.0121(7) C12 0.0609(11) 0.0431(9) 0.0381(8) -0.0055(7) 0.0093(8) -0.0228(8) C13 0.0902(16) 0.0678(13) 0.0385(9) -0.0021(9) -0.0035(10) -0.0313(12) C14 0.0694(12) 0.0547(11) 0.0431(9) -0.0219(8) 0.0207(9) -0.0272(10) C15 0.0428(9) 0.0434(9) 0.0657(12) -0.0212(8) 0.0232(8) -0.0109(7) C16 0.0341(7) 0.0320(7) 0.0475(9) -0.0104(6) 0.0120(7) -0.0106(6) N17 0.0268(6) 0.0322(6) 0.0615(9) -0.0141(6) 0.0107(6) -0.0015(5) C18 0.0262(7) 0.0360(8) 0.0617(10) -0.0115(7) 0.0010(7) -0.0015(6) C19 0.0283(8) 0.0329(8) 0.0699(11) -0.0110(8) 0.0035(7) 0.0053(6) C20 0.0291(7) 0.0291(7) 0.0415(8) -0.0047(6) -0.0036(6) 0.0045(5) C21 0.0294(7) 0.0264(7) 0.0343(7) -0.0027(5) -0.0012(5) 0.0036(5) C22 0.0355(8) 0.0299(7) 0.0484(9) 0.0011(6) 0.0091(6) 0.0050(6) C23 0.0427(9) 0.0353(8) 0.0531(10) 0.0039(7) 0.0127(7) 0.0005(7) C24 0.0482(9) 0.0274(7) 0.0349(7) 0.0005(6) 0.0010(6) -0.0006(6) C25 0.0403(8) 0.0272(7) 0.0413(8) -0.0050(6) -0.0050(6) 0.0053(6) C26 0.0763(13) 0.0292(8) 0.0606(11) 0.0041(7) 0.0144(10) -0.0058(8) C27 0.0504(9) 0.0263(7) 0.0567(10) -0.0026(7) -0.0205(8) -0.0005(7) O28 0.0566(8) 0.0425(7) 0.0929(11) -0.0005(7) -0.0331(8) 0.0108(6) C29 0.0859(15) 0.0530(11) 0.0422(10) 0.0049(8) -0.0101(9) 0.0060(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.12281(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.4767(18) yes O1 . C5 . 1.3469(19) yes C2 . C3 . 1.495(3) yes C2 . C4 . 1.506(3) yes C2 . H21 . 0.993 no C3 . H33 . 0.973 no C3 . H32 . 0.977 no C3 . H31 . 0.996 no C4 . H43 . 0.944 no C4 . H42 . 0.946 no C4 . H41 . 0.985 no C5 . O6 . 1.1967(19) yes C5 . C7 . 1.543(2) yes C7 . N8 . 1.4625(19) yes C7 . C18 . 1.556(2) yes C7 . C27 . 1.559(2) yes N8 . C9 . 1.4637(19) yes N8 . C21 . 1.4444(18) yes C9 . C10 . 1.523(2) yes C9 . H92 . 0.971 no C9 . H91 . 0.978 no C10 . C11 . 1.404(2) yes C10 . C16 . 1.391(2) yes C11 . C12 . 1.389(2) yes C11 . H111 . 0.981 no C12 . C13 . 1.513(3) yes C12 . C14 . 1.388(3) yes C13 . H131 . 0.976 no C13 . H133 . 0.973 no C13 . H132 . 0.953 no C14 . C15 . 1.368(3) yes C14 . H141 . 0.920 no C15 . C16 . 1.411(2) yes C15 . H151 . 0.907 no C16 . N17 . 1.427(2) yes N17 . C18 . 1.450(2) yes N17 . C19 . 1.460(2) yes C18 . H181 . 0.963 no C18 . H182 . 0.995 no C19 . C20 . 1.525(2) yes C19 . H192 . 0.968 no C19 . H191 . 1.023 no C20 . C21 . 1.3994(19) yes C20 . C25 . 1.407(2) yes C21 . C22 . 1.393(2) yes C22 . C23 . 1.379(2) yes C22 . H221 . 0.950 no C23 . C24 . 1.393(2) yes C23 . H231 . 0.960 no C24 . C25 . 1.383(2) yes C24 . C26 . 1.510(2) yes C25 . H251 . 0.941 no C26 . H261 . 0.964 no C26 . H263 . 0.974 no C26 . H262 . 0.942 no C27 . O28 . 1.214(2) yes C27 . C29 . 1.486(3) yes C29 . H292 . 0.931 no C29 . H291 . 0.914 no C29 . H293 . 0.960 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C5 . 116.95(12) yes O1 . C2 . C3 . 108.18(14) yes O1 . C2 . C4 . 106.11(14) yes C3 . C2 . C4 . 113.01(17) yes O1 . C2 . H21 . 106.5 no C3 . C2 . H21 . 110.5 no C4 . C2 . H21 . 112.1 no C2 . C3 . H33 . 111.9 no C2 . C3 . H32 . 109.6 no H33 . C3 . H32 . 109.7 no C2 . C3 . H31 . 110.9 no H33 . C3 . H31 . 108.5 no H32 . C3 . H31 . 106.1 no C2 . C4 . H43 . 109.8 no C2 . C4 . H42 . 111.2 no H43 . C4 . H42 . 109.1 no C2 . C4 . H41 . 109.9 no H43 . C4 . H41 . 107.7 no H42 . C4 . H41 . 109.0 no O1 . C5 . O6 . 124.94(14) yes O1 . C5 . C7 . 108.04(12) yes O6 . C5 . C7 . 127.00(14) yes C5 . C7 . N8 . 110.04(12) yes C5 . C7 . C18 . 107.56(12) yes N8 . C7 . C18 . 112.37(12) yes C5 . C7 . C27 . 104.42(12) yes N8 . C7 . C27 . 108.56(13) yes C18 . C7 . C27 . 113.57(13) yes C7 . N8 . C9 . 115.85(12) yes C7 . N8 . C21 . 115.67(11) yes C9 . N8 . C21 . 114.07(11) yes N8 . C9 . C10 . 117.29(12) yes N8 . C9 . H92 . 107.2 no C10 . C9 . H92 . 110.4 no N8 . C9 . H91 . 107.8 no C10 . C9 . H91 . 104.6 no H92 . C9 . H91 . 109.5 no C9 . C10 . C11 . 117.21(14) yes C9 . C10 . C16 . 123.52(14) yes C11 . C10 . C16 . 119.27(14) yes C10 . C11 . C12 . 122.44(17) yes C10 . C11 . H111 . 119.1 no C12 . C11 . H111 . 118.5 no C11 . C12 . C13 . 121.40(19) yes C11 . C12 . C14 . 117.37(18) yes C13 . C12 . C14 . 121.15(17) yes C12 . C13 . H131 . 111.0 no C12 . C13 . H133 . 111.3 no H131 . C13 . H133 . 108.2 no C12 . C13 . H132 . 112.1 no H131 . C13 . H132 . 106.1 no H133 . C13 . H132 . 108.0 no C12 . C14 . C15 . 121.37(16) yes C12 . C14 . H141 . 118.5 no C15 . C14 . H141 . 120.1 no C14 . C15 . C16 . 121.58(17) yes C14 . C15 . H151 . 124.8 no C16 . C15 . H151 . 113.6 no C15 . C16 . C10 . 117.97(16) yes C15 . C16 . N17 . 117.68(15) yes C10 . C16 . N17 . 124.35(14) yes C16 . N17 . C18 . 117.10(13) yes C16 . N17 . C19 . 115.36(13) yes C18 . N17 . C19 . 114.70(15) yes C7 . C18 . N17 . 113.85(13) yes C7 . C18 . H181 . 105.1 no N17 . C18 . H181 . 109.3 no C7 . C18 . H182 . 108.1 no N17 . C18 . H182 . 109.3 no H181 . C18 . H182 . 111.2 no N17 . C19 . C20 . 116.38(13) yes N17 . C19 . H192 . 110.0 no C20 . C19 . H192 . 108.5 no N17 . C19 . H191 . 106.5 no C20 . C19 . H191 . 107.8 no H192 . C19 . H191 . 107.2 no C19 . C20 . C21 . 124.03(14) yes C19 . C20 . C25 . 117.86(13) yes C21 . C20 . C25 . 118.08(14) yes N8 . C21 . C20 . 124.28(13) yes N8 . C21 . C22 . 116.38(12) yes C20 . C21 . C22 . 119.33(14) yes C21 . C22 . C23 . 121.01(14) yes C21 . C22 . H221 . 119.9 no C23 . C22 . H221 . 119.1 no C22 . C23 . C24 . 120.94(15) yes C22 . C23 . H231 . 121.9 no C24 . C23 . H231 . 117.2 no C23 . C24 . C25 . 117.71(14) yes C23 . C24 . C26 . 120.13(16) yes C25 . C24 . C26 . 122.16(15) yes C20 . C25 . C24 . 122.66(14) yes C20 . C25 . H251 . 117.7 no C24 . C25 . H251 . 119.5 no C24 . C26 . H261 . 113.1 no C24 . C26 . H263 . 111.8 no H261 . C26 . H263 . 105.3 no C24 . C26 . H262 . 112.3 no H261 . C26 . H262 . 109.8 no H263 . C26 . H262 . 103.9 no C7 . C27 . O28 . 120.02(18) yes C7 . C27 . C29 . 117.38(14) yes O28 . C27 . C29 . 122.52(18) yes C27 . C29 . H292 . 113.3 no C27 . C29 . H291 . 107.7 no H292 . C29 . H291 . 108.5 no C27 . C29 . H293 . 109.5 no H292 . C29 . H293 . 108.4 no H291 . C29 . H293 . 109.3 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C13 . H131 . O6 5_564 169 0.98 2.55 3.509(2) yes C19 . H192 . O28 . 120 0.97 2.58 3.177(2) yes C9 . H92 . O6 . 125 0.97 2.34 2.996(2) yes ###### END ######