# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 #TrackingRef '10447_web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1333099354.peptide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 Br N3 O3' _chemical_formula_sum 'C20 H20 Br N3 O3' _chemical_formula_weight 430.30 _chemical_absolute_configuration syn 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.1418(8) _cell_length_b 7.1748(5) _cell_length_c 12.9148(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.5640(10) _cell_angle_gamma 90.00 _cell_volume 994.55(13) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2813 _cell_measurement_theta_min 2.148 _cell_measurement_theta_max 24.75 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 2.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5606 _exptl_absorpt_correction_T_max 0.7950 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5062 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2888 _reflns_number_gt 2627 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.008(8) _refine_ls_number_reflns 2888 _refine_ls_number_parameters 245 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0725 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 Br Br 0.35197(3) 0.37310(7) -0.20763(2) 0.08271(17) Uani 1 1 d . . . O1 O 1.0715(3) 0.1854(6) 0.54825(19) 0.1090(12) Uani 1 1 d . . . O2 O 1.16039(19) 0.1022(3) 0.11899(14) 0.0523(5) Uani 1 1 d . . . O3 O 0.90656(19) 0.0793(3) 0.15847(15) 0.0518(5) Uani 1 1 d . . . N1 N 1.0847(2) 0.1295(3) 0.37906(17) 0.0503(6) Uani 1 1 d . . . H1 H 1.0400 0.1059 0.3150 0.060 Uiso 1 1 calc R . . N2 N 1.11169(18) -0.1459(4) 0.20518(13) 0.0407(5) Uani 1 1 d . . . N3 N 0.82384(19) -0.0606(3) -0.00276(16) 0.0443(6) Uani 1 1 d . . . H3 H 0.8371 -0.1495 -0.0430 0.053 Uiso 1 1 calc R . . C1 C 1.0205(3) 0.1607(6) 0.4528(2) 0.0650(9) Uani 1 1 d . . . C2 C 1.2152(3) 0.1304(4) 0.3928(2) 0.0492(7) Uani 1 1 d . . . C3 C 1.2609(3) 0.0749(4) 0.3068(2) 0.0461(7) Uani 1 1 d . . . C4 C 1.3872(3) 0.0861(5) 0.3155(3) 0.0600(8) Uani 1 1 d . . . H4 H 1.4165 0.0531 0.2570 0.072 Uiso 1 1 calc R . . C5 C 1.4697(3) 0.1444(6) 0.4079(3) 0.0758(11) Uani 1 1 d . . . H5 H 1.5545 0.1498 0.4132 0.091 Uiso 1 1 calc R . . C6 C 1.4244(3) 0.1959(6) 0.4942(3) 0.0802(11) Uani 1 1 d . . . H6 H 1.4799 0.2354 0.5578 0.096 Uiso 1 1 calc R . . C7 C 1.2996(3) 0.1894(6) 0.4873(3) 0.0688(9) Uani 1 1 d . . . H7 H 1.2713 0.2244 0.5459 0.083 Uiso 1 1 calc R . . C8 C 1.1742(2) 0.0111(4) 0.2016(2) 0.0399(6) Uani 1 1 d . . . C9 C 1.0052(2) -0.1987(4) 0.1159(2) 0.0424(6) Uani 1 1 d . . . H9 H 1.0324 -0.2261 0.0514 0.051 Uiso 1 1 calc R . . C10 C 0.9549(3) -0.3762(5) 0.1570(3) 0.0606(9) Uani 1 1 d . . . H10A H 0.8857 -0.3467 0.1865 0.073 Uiso 1 1 calc R . . H10B H 0.9272 -0.4661 0.0995 0.073 Uiso 1 1 calc R . . C11 C 1.0646(3) -0.4516(5) 0.2438(3) 0.0656(9) Uani 1 1 d . . . H11A H 1.0363 -0.5236 0.2963 0.079 Uiso 1 1 calc R . . H11B H 1.1170 -0.5298 0.2129 0.079 Uiso 1 1 calc R . . C12 C 1.1335(3) -0.2807(5) 0.2941(2) 0.0556(8) Uani 1 1 d . . . H12A H 1.1009 -0.2347 0.3518 0.067 Uiso 1 1 calc R . . H12B H 1.2218 -0.3064 0.3225 0.067 Uiso 1 1 calc R . . C13 C 0.9086(2) -0.0425(4) 0.0937(2) 0.0410(6) Uani 1 1 d . . . C14 C 0.7161(2) 0.0483(4) -0.0459(2) 0.0436(6) Uani 1 1 d . . . C15 C 0.6335(3) -0.0186(5) -0.1378(3) 0.0635(9) Uani 1 1 d . . . H15 H 0.6510 -0.1297 -0.1679 0.076 Uiso 1 1 calc R . . C16 C 0.5253(3) 0.0765(6) -0.1858(3) 0.0692(10) Uani 1 1 d . . . H16 H 0.4700 0.0300 -0.2477 0.083 Uiso 1 1 calc R . . C17 C 0.5004(3) 0.2385(5) -0.1417(2) 0.0582(9) Uani 1 1 d . . . C18 C 0.5815(3) 0.3108(5) -0.0512(2) 0.0637(9) Uani 1 1 d . . . H18 H 0.5639 0.4231 -0.0225 0.076 Uiso 1 1 calc R . . C19 C 0.6901(3) 0.2144(5) -0.0032(2) 0.0563(8) Uani 1 1 d . . . H19 H 0.7456 0.2622 0.0582 0.068 Uiso 1 1 calc R . . C20 C 0.8824(3) 0.1657(7) 0.4082(3) 0.0777(11) Uani 1 1 d . . . H20A H 0.8455 0.0671 0.4395 0.117 Uiso 1 1 calc R . . H20B H 0.8616 0.1495 0.3316 0.117 Uiso 1 1 calc R . . H20C H 0.8512 0.2835 0.4247 0.117 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 Br 0.05307(18) 0.1196(4) 0.0742(2) 0.0089(3) 0.01500(14) 0.0308(2) O1 0.100(2) 0.179(4) 0.0512(15) -0.0364(19) 0.0257(14) -0.012(2) O2 0.0642(12) 0.0501(13) 0.0424(10) 0.0139(10) 0.0137(9) -0.0052(10) O3 0.0521(12) 0.0531(13) 0.0461(11) -0.0134(11) 0.0064(9) 0.0086(10) N1 0.0617(14) 0.0507(16) 0.0387(12) -0.0054(11) 0.0141(10) 0.0011(12) N2 0.0497(10) 0.0391(14) 0.0336(10) 0.0062(12) 0.0115(8) 0.0024(13) N3 0.0490(12) 0.0462(15) 0.0362(11) -0.0075(10) 0.0089(9) 0.0054(10) C1 0.087(2) 0.064(2) 0.0480(18) -0.0115(17) 0.0239(16) -0.0029(19) C2 0.0609(17) 0.0397(17) 0.0411(15) 0.0018(13) 0.0036(12) 0.0016(14) C3 0.0497(15) 0.0369(16) 0.0483(15) 0.0075(14) 0.0071(12) 0.0004(13) C4 0.0532(17) 0.060(2) 0.0651(18) 0.0103(18) 0.0123(14) 0.0047(15) C5 0.0517(18) 0.082(3) 0.081(2) 0.004(2) -0.0053(17) -0.0042(18) C6 0.073(2) 0.075(3) 0.072(2) -0.014(2) -0.0159(19) -0.004(2) C7 0.078(2) 0.066(2) 0.0535(18) -0.0122(18) 0.0019(16) -0.0005(19) C8 0.0431(14) 0.0390(16) 0.0383(14) 0.0051(13) 0.0124(11) 0.0048(12) C9 0.0507(15) 0.0411(16) 0.0363(12) -0.0010(12) 0.0132(11) -0.0007(12) C10 0.065(2) 0.0419(19) 0.075(2) 0.0038(17) 0.0180(16) -0.0071(16) C11 0.095(2) 0.044(2) 0.0583(19) 0.0075(17) 0.0219(17) -0.0036(18) C12 0.084(2) 0.0405(18) 0.0435(16) 0.0116(14) 0.0188(14) 0.0063(16) C13 0.0486(15) 0.0393(16) 0.0382(14) -0.0006(13) 0.0174(11) -0.0011(12) C14 0.0490(15) 0.0467(17) 0.0357(13) -0.0021(13) 0.0124(11) 0.0034(13) C15 0.0627(19) 0.070(2) 0.0523(17) -0.0160(16) 0.0058(14) 0.0117(17) C16 0.0592(19) 0.087(3) 0.0520(17) -0.012(2) -0.0006(14) 0.0084(18) C17 0.0457(15) 0.082(3) 0.0483(16) 0.0042(17) 0.0150(13) 0.0135(16) C18 0.0643(18) 0.068(3) 0.0559(17) -0.0082(17) 0.0110(14) 0.0165(17) C19 0.0590(18) 0.058(2) 0.0463(15) -0.0060(15) 0.0051(13) 0.0071(16) C20 0.072(2) 0.099(3) 0.071(2) -0.025(2) 0.0351(18) -0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br C17 1.907(3) . ? O1 C1 1.224(4) . ? O2 C8 1.226(3) . ? O3 C13 1.214(3) . ? N1 C1 1.354(4) . ? N1 C2 1.417(4) . ? N1 H1 0.8600 . ? N2 C8 1.332(4) . ? N2 C9 1.465(3) . ? N2 C12 1.472(4) . ? N3 C13 1.352(3) . ? N3 C14 1.415(3) . ? N3 H3 0.8600 . ? C1 C20 1.492(5) . ? C2 C7 1.392(4) . ? C2 C3 1.398(4) . ? C3 C4 1.384(4) . ? C3 C8 1.511(4) . ? C4 C5 1.362(5) . ? C4 H4 0.9300 . ? C5 C6 1.391(6) . ? C5 H5 0.9300 . ? C6 C7 1.370(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 C13 1.526(4) . ? C9 C10 1.542(4) . ? C9 H9 0.9800 . ? C10 C11 1.519(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.499(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 C19 1.376(4) . ? C14 C15 1.378(4) . ? C15 C16 1.379(5) . ? C15 H15 0.9300 . ? C16 C17 1.355(5) . ? C16 H16 0.9300 . ? C17 C18 1.374(4) . ? C18 C19 1.387(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 C2 129.0(2) . . ? C1 N1 H1 115.5 . . ? C2 N1 H1 115.5 . . ? C8 N2 C9 120.8(2) . . ? C8 N2 C12 127.2(2) . . ? C9 N2 C12 112.0(2) . . ? C13 N3 C14 128.2(2) . . ? C13 N3 H3 115.9 . . ? C14 N3 H3 115.9 . . ? O1 C1 N1 122.8(3) . . ? O1 C1 C20 122.5(3) . . ? N1 C1 C20 114.7(3) . . ? C7 C2 C3 118.6(3) . . ? C7 C2 N1 122.8(3) . . ? C3 C2 N1 118.6(2) . . ? C4 C3 C2 119.9(3) . . ? C4 C3 C8 118.8(3) . . ? C2 C3 C8 121.3(2) . . ? C5 C4 C3 121.4(3) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 118.6(3) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C7 C6 C5 121.2(3) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C2 120.2(3) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? O2 C8 N2 122.4(2) . . ? O2 C8 C3 121.5(3) . . ? N2 C8 C3 116.1(2) . . ? N2 C9 C13 109.9(2) . . ? N2 C9 C10 103.6(2) . . ? C13 C9 C10 111.6(2) . . ? N2 C9 H9 110.5 . . ? C13 C9 H9 110.5 . . ? C10 C9 H9 110.5 . . ? C11 C10 C9 104.7(3) . . ? C11 C10 H10A 110.8 . . ? C9 C10 H10A 110.8 . . ? C11 C10 H10B 110.8 . . ? C9 C10 H10B 110.8 . . ? H10A C10 H10B 108.9 . . ? C12 C11 C10 104.2(3) . . ? C12 C11 H11A 110.9 . . ? C10 C11 H11A 110.9 . . ? C12 C11 H11B 110.9 . . ? C10 C11 H11B 110.9 . . ? H11A C11 H11B 108.9 . . ? N2 C12 C11 103.9(2) . . ? N2 C12 H12A 111.0 . . ? C11 C12 H12A 111.0 . . ? N2 C12 H12B 111.0 . . ? C11 C12 H12B 111.0 . . ? H12A C12 H12B 109.0 . . ? O3 C13 N3 124.5(3) . . ? O3 C13 C9 122.8(2) . . ? N3 C13 C9 112.7(2) . . ? C19 C14 C15 118.9(3) . . ? C19 C14 N3 124.6(2) . . ? C15 C14 N3 116.5(3) . . ? C14 C15 C16 121.1(3) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 119.2(3) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 121.3(3) . . ? C16 C17 Br 119.9(2) . . ? C18 C17 Br 118.9(3) . . ? C17 C18 C19 119.3(3) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C14 C19 C18 120.3(3) . . ? C14 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C1 C20 H20A 109.5 . . ? C1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 -4.3(6) . . . . ? C2 N1 C1 C20 174.7(3) . . . . ? C1 N1 C2 C7 -8.5(5) . . . . ? C1 N1 C2 C3 173.4(3) . . . . ? C7 C2 C3 C4 -2.5(4) . . . . ? N1 C2 C3 C4 175.7(3) . . . . ? C7 C2 C3 C8 -179.4(3) . . . . ? N1 C2 C3 C8 -1.2(4) . . . . ? C2 C3 C4 C5 2.3(5) . . . . ? C8 C3 C4 C5 179.3(3) . . . . ? C3 C4 C5 C6 -0.9(6) . . . . ? C4 C5 C6 C7 -0.3(7) . . . . ? C5 C6 C7 C2 0.0(7) . . . . ? C3 C2 C7 C6 1.3(5) . . . . ? N1 C2 C7 C6 -176.8(4) . . . . ? C9 N2 C8 O2 -12.2(4) . . . . ? C12 N2 C8 O2 170.1(3) . . . . ? C9 N2 C8 C3 165.8(2) . . . . ? C12 N2 C8 C3 -11.9(4) . . . . ? C4 C3 C8 O2 -64.3(4) . . . . ? C2 C3 C8 O2 112.7(3) . . . . ? C4 C3 C8 N2 117.6(3) . . . . ? C2 C3 C8 N2 -65.4(4) . . . . ? C8 N2 C9 C13 -55.9(3) . . . . ? C12 N2 C9 C13 122.1(2) . . . . ? C8 N2 C9 C10 -175.3(2) . . . . ? C12 N2 C9 C10 2.7(3) . . . . ? N2 C9 C10 C11 -22.4(3) . . . . ? C13 C9 C10 C11 -140.5(3) . . . . ? C9 C10 C11 C12 33.8(3) . . . . ? C8 N2 C12 C11 -163.9(3) . . . . ? C9 N2 C12 C11 18.2(3) . . . . ? C10 C11 C12 N2 -31.6(3) . . . . ? C14 N3 C13 O3 -2.7(5) . . . . ? C14 N3 C13 C9 174.3(2) . . . . ? N2 C9 C13 O3 -18.3(4) . . . . ? C10 C9 C13 O3 96.0(3) . . . . ? N2 C9 C13 N3 164.6(2) . . . . ? C10 C9 C13 N3 -81.1(3) . . . . ? C13 N3 C14 C19 11.7(5) . . . . ? C13 N3 C14 C15 -169.0(3) . . . . ? C19 C14 C15 C16 -1.1(5) . . . . ? N3 C14 C15 C16 179.6(3) . . . . ? C14 C15 C16 C17 0.2(6) . . . . ? C15 C16 C17 C18 0.9(6) . . . . ? C15 C16 C17 Br 179.5(3) . . . . ? C16 C17 C18 C19 -1.0(5) . . . . ? Br C17 C18 C19 -179.6(2) . . . . ? C15 C14 C19 C18 1.0(5) . . . . ? N3 C14 C19 C18 -179.8(3) . . . . ? C17 C18 C19 C14 0.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.375 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 874039' ####################################################################### # # 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_Boc-Pro-Ant-Pro-NHMe _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Peptide _chemical_melting_point ? _chemical_formula_moiety 'C23 H32 N4 O5' _chemical_formula_sum 'C23 H32 N4 O5' _chemical_formula_weight 444.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.9732(8) _cell_length_b 10.4292(9) _cell_length_c 25.653(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2400.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1545 _cell_measurement_theta_min 2.405 _cell_measurement_theta_max 18.219 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9849 _exptl_absorpt_correction_T_max 0.9896 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12181 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4239 _reflns_number_gt 2463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL and PLATON' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.0000P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.4(18) _refine_ls_number_reflns 4239 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1041 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1394 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.2652(4) 0.2347(3) 0.31366(11) 0.1131(11) Uani 1 1 d . . . O2 O 0.1075(3) 0.1675(3) 0.24943(9) 0.0777(8) Uani 1 1 d . . . O3 O 0.3953(5) 0.0370(3) 0.18854(12) 0.1339(15) Uani 1 1 d . . . O4 O 0.1106(3) 0.0591(3) -0.01738(10) 0.0730(7) Uani 1 1 d . . . O5 O 0.1066(3) 0.2685(2) 0.06444(11) 0.0818(8) Uani 1 1 d . . . N1 N 0.3152(3) 0.2681(3) 0.22812(11) 0.0658(8) Uani 1 1 d . . . N2 N 0.2636(3) 0.0613(2) 0.11446(10) 0.0536(7) Uani 1 1 d . . . H2 H 0.2098 0.1159 0.0978 0.064 Uiso 1 1 calc R . . N3 N -0.0342(3) 0.0404(2) 0.05326(10) 0.0515(7) Uani 1 1 d . . . N4 N -0.0807(3) 0.3844(3) 0.03294(12) 0.0719(9) Uani 1 1 d . . . H4 H -0.1699 0.3836 0.0207 0.086 Uiso 1 1 calc R . . C1 C 0.2333(5) 0.2221(4) 0.26802(17) 0.0789(12) Uani 1 1 d . . . C2 C 0.2882(4) 0.2419(3) 0.17321(12) 0.0554(8) Uani 1 1 d . . . H2A H 0.1849 0.2626 0.1640 0.066 Uiso 1 1 calc R . . C3 C 0.3954(5) 0.3332(4) 0.14613(17) 0.0852(12) Uani 1 1 d . . . H3A H 0.4335 0.2955 0.1142 0.102 Uiso 1 1 calc R . . H3B H 0.3464 0.4135 0.1378 0.102 Uiso 1 1 calc R . . C4 C 0.5172(6) 0.3537(7) 0.1842(2) 0.162(3) Uani 1 1 d . . . H4A H 0.5542 0.4408 0.1814 0.194 Uiso 1 1 calc R . . H4B H 0.5988 0.2954 0.1769 0.194 Uiso 1 1 calc R . . C5 C 0.4591(4) 0.3304(5) 0.23766(19) 0.1008(16) Uani 1 1 d . . . H5A H 0.5253 0.2749 0.2572 0.121 Uiso 1 1 calc R . . H5B H 0.4464 0.4103 0.2565 0.121 Uiso 1 1 calc R . . C6 C 0.3228(4) 0.1029(3) 0.16023(14) 0.0626(10) Uani 1 1 d . . . C7 C 0.2793(4) -0.0600(3) 0.09097(12) 0.0491(8) Uani 1 1 d . . . C8 C 0.3834(4) -0.1506(3) 0.10807(13) 0.0589(9) Uani 1 1 d . . . H8 H 0.4443 -0.1323 0.1365 0.071 Uiso 1 1 calc R . . C9 C 0.3959(4) -0.2673(3) 0.08277(15) 0.0674(10) Uani 1 1 d . . . H9 H 0.4627 -0.3283 0.0952 0.081 Uiso 1 1 calc R . . C10 C 0.3117(4) -0.2942(3) 0.03997(16) 0.0733(11) Uani 1 1 d . . . H10 H 0.3240 -0.3717 0.0226 0.088 Uiso 1 1 calc R . . C11 C 0.2088(4) -0.2069(3) 0.02249(15) 0.0671(10) Uani 1 1 d . . . H11 H 0.1509 -0.2263 -0.0065 0.081 Uiso 1 1 calc R . . C12 C 0.1902(3) -0.0890(3) 0.04785(13) 0.0526(8) Uani 1 1 d . . . C13 C 0.0856(4) 0.0077(3) 0.02544(14) 0.0534(8) Uani 1 1 d . . . C14 C -0.0911(4) -0.0250(4) 0.09970(15) 0.0696(10) Uani 1 1 d . . . H14A H -0.0331 -0.0030 0.1303 0.084 Uiso 1 1 calc R . . H14B H -0.0901 -0.1173 0.0951 0.084 Uiso 1 1 calc R . . C15 C -0.2455(5) 0.0241(6) 0.10394(19) 0.1184(18) Uani 1 1 d . . . H15A H -0.3136 -0.0309 0.0849 0.142 Uiso 1 1 calc R . . H15B H -0.2764 0.0268 0.1402 0.142 Uiso 1 1 calc R . . C16 C -0.2457(4) 0.1539(4) 0.08155(17) 0.0861(12) Uani 1 1 d . . . H16A H -0.2286 0.2174 0.1085 0.103 Uiso 1 1 calc R . . H16B H -0.3405 0.1719 0.0649 0.103 Uiso 1 1 calc R . . C17 C -0.1197(3) 0.1566(3) 0.04150(13) 0.0551(8) Uani 1 1 d . . . H17 H -0.1606 0.1518 0.0061 0.066 Uiso 1 1 calc R . . C18 C -0.0208(4) 0.2749(3) 0.04703(14) 0.0582(9) Uani 1 1 d . . . C19 C -0.0045(4) 0.5063(3) 0.03700(17) 0.0822(12) Uani 1 1 d . . . H19A H -0.0598 0.5624 0.0595 0.123 Uiso 1 1 calc R . . H19B H 0.0036 0.5444 0.0030 0.123 Uiso 1 1 calc R . . H19C H 0.0934 0.4931 0.0511 0.123 Uiso 1 1 calc R . . C20 C 0.0023(5) 0.1034(4) 0.28464(17) 0.0813(12) Uani 1 1 d . . . C21 C -0.0635(6) 0.1980(5) 0.32293(19) 0.1155(17) Uani 1 1 d . . . H21A H 0.0125 0.2260 0.3467 0.173 Uiso 1 1 calc R . . H21B H -0.1424 0.1575 0.3421 0.173 Uiso 1 1 calc R . . H21C H -0.1024 0.2706 0.3043 0.173 Uiso 1 1 calc R . . C22 C 0.0761(7) -0.0094(4) 0.3108(2) 0.1210(17) Uani 1 1 d . . . H22A H 0.1241 -0.0618 0.2850 0.181 Uiso 1 1 calc R . . H22B H 0.0023 -0.0592 0.3288 0.181 Uiso 1 1 calc R . . H22C H 0.1489 0.0209 0.3353 0.181 Uiso 1 1 calc R . . C23 C -0.1159(5) 0.0566(5) 0.24703(19) 0.1116(16) Uani 1 1 d . . . H23A H -0.1665 0.1288 0.2321 0.167 Uiso 1 1 calc R . . H23B H -0.1863 0.0040 0.2654 0.167 Uiso 1 1 calc R . . H23C H -0.0697 0.0073 0.2199 0.167 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 0.143(3) 0.137(3) 0.0596(16) -0.0222(18) -0.0119(18) -0.026(2) O2 0.0884(18) 0.0797(17) 0.0649(15) -0.0070(15) 0.0069(16) -0.0232(16) O3 0.201(4) 0.099(2) 0.101(2) -0.0357(19) -0.083(3) 0.084(3) O4 0.0542(13) 0.1034(19) 0.0615(15) 0.0154(15) 0.0051(13) 0.0035(14) O5 0.0670(15) 0.0578(15) 0.121(2) 0.0124(15) -0.0413(16) 0.0001(14) N1 0.0561(17) 0.077(2) 0.0638(19) -0.0203(17) -0.0069(16) -0.0076(16) N2 0.0541(16) 0.0471(16) 0.0596(17) -0.0066(14) -0.0130(14) 0.0106(14) N3 0.0453(15) 0.0515(16) 0.0578(17) 0.0050(14) 0.0031(14) -0.0028(13) N4 0.0534(16) 0.065(2) 0.098(2) 0.0156(18) -0.0190(17) -0.0007(17) C1 0.094(3) 0.071(3) 0.072(3) -0.014(2) -0.006(3) -0.005(3) C2 0.0536(19) 0.051(2) 0.062(2) -0.0074(17) -0.0035(18) 0.0055(17) C3 0.075(3) 0.081(3) 0.100(3) -0.006(2) 0.006(3) -0.018(2) C4 0.112(4) 0.255(8) 0.117(5) -0.039(5) 0.012(4) -0.100(5) C5 0.067(3) 0.129(4) 0.106(4) -0.038(3) -0.014(3) -0.023(3) C6 0.062(2) 0.062(2) 0.064(2) -0.004(2) -0.020(2) 0.0177(19) C7 0.0482(19) 0.0421(18) 0.0569(19) -0.0007(16) 0.0053(17) 0.0015(16) C8 0.059(2) 0.053(2) 0.065(2) -0.0003(19) 0.0080(18) 0.0083(19) C9 0.061(2) 0.051(2) 0.090(3) 0.001(2) 0.012(2) 0.006(2) C10 0.067(2) 0.053(2) 0.100(3) -0.022(2) 0.025(3) -0.001(2) C11 0.058(2) 0.065(2) 0.079(2) -0.019(2) 0.005(2) -0.006(2) C12 0.0469(17) 0.051(2) 0.060(2) -0.0087(17) 0.0033(18) -0.0043(16) C13 0.0459(19) 0.058(2) 0.056(2) -0.0078(19) -0.0035(19) -0.0085(18) C14 0.066(2) 0.070(2) 0.073(2) 0.014(2) 0.007(2) 0.001(2) C15 0.078(3) 0.159(5) 0.118(4) 0.058(4) 0.035(3) 0.030(3) C16 0.069(2) 0.076(3) 0.113(3) 0.007(3) 0.030(2) 0.007(2) C17 0.0435(17) 0.060(2) 0.062(2) 0.0071(18) 0.0011(17) 0.0014(18) C18 0.049(2) 0.058(2) 0.067(2) 0.0105(19) -0.0060(19) 0.0044(19) C19 0.088(3) 0.057(2) 0.102(3) 0.011(2) -0.017(3) 0.002(2) C20 0.099(3) 0.063(3) 0.082(3) -0.007(2) 0.018(3) -0.008(2) C21 0.138(4) 0.096(3) 0.112(4) -0.023(3) 0.050(3) -0.005(3) C22 0.165(5) 0.078(3) 0.119(4) 0.016(3) 0.016(4) 0.006(4) C23 0.107(4) 0.120(4) 0.108(4) 0.007(3) 0.013(3) -0.043(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 C1 1.212(4) . ? O2 C1 1.351(5) . ? O2 C20 1.468(5) . ? O3 C6 1.193(4) . ? O4 C13 1.243(4) . ? O5 C18 1.230(4) . ? N1 C1 1.348(5) . ? N1 C2 1.455(4) . ? N1 C5 1.466(5) . ? N2 C6 1.360(4) . ? N2 C7 1.409(4) . ? N2 H2 0.8600 . ? N3 C13 1.335(4) . ? N3 C14 1.465(4) . ? N3 C17 1.465(4) . ? N4 C18 1.313(4) . ? N4 C19 1.448(4) . ? N4 H4 0.8600 . ? C2 C6 1.519(5) . ? C2 C3 1.521(5) . ? C2 H2A 0.9800 . ? C3 C4 1.480(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.488(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C7 C12 1.398(4) . ? C7 C8 1.399(4) . ? C8 C9 1.384(5) . ? C8 H8 0.9300 . ? C9 C10 1.362(5) . ? C9 H9 0.9300 . ? C10 C11 1.371(5) . ? C10 H10 0.9300 . ? C11 C12 1.402(4) . ? C11 H11 0.9300 . ? C12 C13 1.492(5) . ? C14 C15 1.481(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.470(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.528(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.527(5) . ? C17 H17 0.9800 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C22 1.509(6) . ? C20 C21 1.512(5) . ? C20 C23 1.514(6) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 O2 C20 120.8(3) . . ? C1 N1 C2 125.3(3) . . ? C1 N1 C5 120.7(3) . . ? C2 N1 C5 113.1(3) . . ? C6 N2 C7 128.1(3) . . ? C6 N2 H2 116.0 . . ? C7 N2 H2 116.0 . . ? C13 N3 C14 126.6(3) . . ? C13 N3 C17 121.6(3) . . ? C14 N3 C17 111.7(3) . . ? C18 N4 C19 123.4(3) . . ? C18 N4 H4 118.3 . . ? C19 N4 H4 118.3 . . ? O1 C1 N1 124.5(4) . . ? O1 C1 O2 125.7(4) . . ? N1 C1 O2 109.7(3) . . ? N1 C2 C6 110.9(3) . . ? N1 C2 C3 102.7(3) . . ? C6 C2 C3 111.6(3) . . ? N1 C2 H2A 110.5 . . ? C6 C2 H2A 110.5 . . ? C3 C2 H2A 110.5 . . ? C4 C3 C2 104.9(4) . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3A 110.8 . . ? C4 C3 H3B 110.8 . . ? C2 C3 H3B 110.8 . . ? H3A C3 H3B 108.9 . . ? C3 C4 C5 109.0(4) . . ? C3 C4 H4A 109.9 . . ? C5 C4 H4A 109.9 . . ? C3 C4 H4B 109.9 . . ? C5 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? N1 C5 C4 103.1(4) . . ? N1 C5 H5A 111.1 . . ? C4 C5 H5A 111.1 . . ? N1 C5 H5B 111.1 . . ? C4 C5 H5B 111.1 . . ? H5A C5 H5B 109.1 . . ? O3 C6 N2 123.7(3) . . ? O3 C6 C2 121.8(3) . . ? N2 C6 C2 114.4(3) . . ? C12 C7 C8 119.0(3) . . ? C12 C7 N2 118.4(3) . . ? C8 C7 N2 122.7(3) . . ? C9 C8 C7 120.1(3) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C10 C9 C8 120.9(4) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.0(3) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 120.7(3) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C7 C12 C11 119.2(3) . . ? C7 C12 C13 121.2(3) . . ? C11 C12 C13 119.3(3) . . ? O4 C13 N3 120.5(3) . . ? O4 C13 C12 121.3(3) . . ? N3 C13 C12 118.2(3) . . ? N3 C14 C15 103.0(3) . . ? N3 C14 H14A 111.2 . . ? C15 C14 H14A 111.2 . . ? N3 C14 H14B 111.2 . . ? C15 C14 H14B 111.2 . . ? H14A C14 H14B 109.1 . . ? C16 C15 C14 106.9(4) . . ? C16 C15 H15A 110.3 . . ? C14 C15 H15A 110.3 . . ? C16 C15 H15B 110.3 . . ? C14 C15 H15B 110.3 . . ? H15A C15 H15B 108.6 . . ? C15 C16 C17 106.2(3) . . ? C15 C16 H16A 110.5 . . ? C17 C16 H16A 110.5 . . ? C15 C16 H16B 110.5 . . ? C17 C16 H16B 110.5 . . ? H16A C16 H16B 108.7 . . ? N3 C17 C18 110.2(2) . . ? N3 C17 C16 103.5(3) . . ? C18 C17 C16 112.5(3) . . ? N3 C17 H17 110.2 . . ? C18 C17 H17 110.2 . . ? C16 C17 H17 110.2 . . ? O5 C18 N4 121.9(3) . . ? O5 C18 C17 122.0(3) . . ? N4 C18 C17 116.1(3) . . ? N4 C19 H19A 109.5 . . ? N4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 C20 C22 110.3(4) . . ? O2 C20 C21 110.7(3) . . ? C22 C20 C21 113.0(4) . . ? O2 C20 C23 101.8(3) . . ? C22 C20 C23 109.9(4) . . ? C21 C20 C23 110.5(4) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 172.7(4) . . . . ? C5 N1 C1 O1 4.7(6) . . . . ? C2 N1 C1 O2 -11.0(5) . . . . ? C5 N1 C1 O2 -178.9(3) . . . . ? C20 O2 C1 O1 -7.1(6) . . . . ? C20 O2 C1 N1 176.6(3) . . . . ? C1 N1 C2 C6 -69.4(4) . . . . ? C5 N1 C2 C6 99.4(4) . . . . ? C1 N1 C2 C3 171.3(4) . . . . ? C5 N1 C2 C3 -19.9(4) . . . . ? N1 C2 C3 C4 26.5(5) . . . . ? C6 C2 C3 C4 -92.4(4) . . . . ? C2 C3 C4 C5 -25.0(6) . . . . ? C1 N1 C5 C4 174.4(4) . . . . ? C2 N1 C5 C4 5.1(5) . . . . ? C3 C4 C5 N1 12.8(6) . . . . ? C7 N2 C6 O3 -2.7(6) . . . . ? C7 N2 C6 C2 177.8(3) . . . . ? N1 C2 C6 O3 -16.6(5) . . . . ? C3 C2 C6 O3 97.2(4) . . . . ? N1 C2 C6 N2 163.0(3) . . . . ? C3 C2 C6 N2 -83.2(4) . . . . ? C6 N2 C7 C12 170.2(3) . . . . ? C6 N2 C7 C8 -11.8(5) . . . . ? C12 C7 C8 C9 -0.7(5) . . . . ? N2 C7 C8 C9 -178.7(3) . . . . ? C7 C8 C9 C10 2.4(5) . . . . ? C8 C9 C10 C11 -2.4(5) . . . . ? C9 C10 C11 C12 0.8(5) . . . . ? C8 C7 C12 C11 -0.9(4) . . . . ? N2 C7 C12 C11 177.2(3) . . . . ? C8 C7 C12 C13 -175.3(3) . . . . ? N2 C7 C12 C13 2.8(4) . . . . ? C10 C11 C12 C7 0.9(5) . . . . ? C10 C11 C12 C13 175.4(3) . . . . ? C14 N3 C13 O4 169.5(3) . . . . ? C17 N3 C13 O4 -14.9(4) . . . . ? C14 N3 C13 C12 -12.3(4) . . . . ? C17 N3 C13 C12 163.4(3) . . . . ? C7 C12 C13 O4 108.7(4) . . . . ? C11 C12 C13 O4 -65.7(4) . . . . ? C7 C12 C13 N3 -69.6(4) . . . . ? C11 C12 C13 N3 116.1(3) . . . . ? C13 N3 C14 C15 -162.8(4) . . . . ? C17 N3 C14 C15 21.2(4) . . . . ? N3 C14 C15 C16 -29.5(5) . . . . ? C14 C15 C16 C17 27.3(5) . . . . ? C13 N3 C17 C18 -60.7(4) . . . . ? C14 N3 C17 C18 115.6(3) . . . . ? C13 N3 C17 C16 178.9(3) . . . . ? C14 N3 C17 C16 -4.9(4) . . . . ? C15 C16 C17 N3 -13.7(4) . . . . ? C15 C16 C17 C18 -132.6(4) . . . . ? C19 N4 C18 O5 -0.7(6) . . . . ? C19 N4 C18 C17 178.2(3) . . . . ? N3 C17 C18 O5 -7.1(5) . . . . ? C16 C17 C18 O5 107.9(4) . . . . ? N3 C17 C18 N4 174.0(3) . . . . ? C16 C17 C18 N4 -71.0(4) . . . . ? C1 O2 C20 C22 -62.4(5) . . . . ? C1 O2 C20 C21 63.4(5) . . . . ? C1 O2 C20 C23 -179.0(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.250 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.031 _database_code_depnum_ccdc_archive 'CCDC 699500' ####################################################################### # # 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_3 #TrackingRef '10447_web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1333099354.peptide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H22 Br N3 O4' _chemical_formula_sum 'C21 H22 Br N3 O4' _chemical_formula_weight 460.33 _chemical_absolute_configuration syn 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.1599(7) _cell_length_b 11.8460(11) _cell_length_c 25.160(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2134.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2359 _cell_measurement_theta_min 2.958 _cell_measurement_theta_max 28.175 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 1.958 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7473 _exptl_absorpt_correction_T_max 0.9675 _exptl_absorpt_process_details "Bruker's SADABS" _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17385 _diffrn_reflns_av_R_equivalents 0.0724 _diffrn_reflns_av_sigmaI/netI 0.0698 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3754 _reflns_number_gt 2768 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+0.0329P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.022(16) _refine_ls_number_reflns 3754 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1049 _refine_ls_R_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.1330 _refine_ls_wR_factor_gt 0.1234 _refine_ls_goodness_of_fit_ref 1.203 _refine_ls_restrained_S_all 1.203 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.36242(14) 0.82443(7) -0.10268(3) 0.0930(4) Uani 1 1 d . . . O1 O 0.2206(6) 0.4571(4) 0.19606(18) 0.0681(13) Uani 1 1 d . . . O2 O 0.3124(8) 0.3328(5) 0.25709(19) 0.0932(17) Uani 1 1 d . . . O3 O 0.1000(6) 0.1443(3) 0.05456(15) 0.0558(12) Uani 1 1 d . . . O4 O 0.0813(6) 0.3989(3) 0.07577(15) 0.0579(12) Uani 1 1 d . B . N1 N 0.1524(7) 0.2801(4) 0.18253(18) 0.0539(13) Uani 1 1 d . . . H1 H 0.1013 0.3088 0.1547 0.065 Uiso 1 1 calc R . . N2 N -0.1456(6) 0.2191(3) 0.09761(16) 0.0399(10) Uani 1 1 d . B . N3 N -0.0520(6) 0.4272(4) -0.00511(17) 0.0435(12) Uani 1 1 d . B . H3 H -0.1379 0.4011 -0.0256 0.052 Uiso 1 1 calc R . . C1 C 0.2363(9) 0.3536(6) 0.2164(3) 0.0536(18) Uani 1 1 d . . . C2 C 0.1400(9) 0.1614(6) 0.1879(2) 0.0520(15) Uani 1 1 d . . . C3 C 0.0680(8) 0.0988(5) 0.1460(2) 0.0445(15) Uani 1 1 d . . . C4 C 0.0581(9) -0.0170(6) 0.1505(3) 0.067(2) Uani 1 1 d . . . H4 H 0.0106 -0.0591 0.1224 0.080 Uiso 1 1 calc R . . C5 C 0.1160(12) -0.0707(7) 0.1951(4) 0.087(2) Uani 1 1 d . . . H5 H 0.1069 -0.1489 0.1972 0.104 Uiso 1 1 calc R . . C6 C 0.1869(12) -0.0119(8) 0.2364(4) 0.095(3) Uani 1 1 d . . . H6 H 0.2282 -0.0496 0.2666 0.114 Uiso 1 1 calc R . . C7 C 0.1979(9) 0.1054(8) 0.2336(3) 0.076(2) Uani 1 1 d . . . H7 H 0.2442 0.1462 0.2623 0.091 Uiso 1 1 calc R . . C8 C 0.0084(8) 0.1549(4) 0.0954(2) 0.0405(13) Uani 1 1 d . . . C9 C -0.1931(7) 0.2930(5) 0.0532(2) 0.0398(14) Uani 1 1 d . B . H9 H -0.2197 0.2484 0.0213 0.048 Uiso 1 1 calc R . . C10 C -0.3705(10) 0.3541(5) 0.0723(2) 0.0603(18) Uani 1 1 d . . . H10A H -0.3742 0.4309 0.0590 0.072 Uiso 1 1 calc R A 1 H10B H -0.4818 0.3146 0.0605 0.072 Uiso 1 1 calc R A 1 C11 C -0.357(2) 0.3528(12) 0.1299(6) 0.061(4) Uani 0.50 1 d P B 1 H11A H -0.4784 0.3627 0.1462 0.074 Uiso 0.50 1 calc PR B 1 H11B H -0.2736 0.4116 0.1425 0.074 Uiso 0.50 1 calc PR B 1 C11' C -0.4366(19) 0.2831(15) 0.1186(5) 0.063(4) Uani 0.50 1 d P B 2 H11C H -0.5003 0.3301 0.1445 0.076 Uiso 0.50 1 calc PR B 2 H11D H -0.5229 0.2256 0.1064 0.076 Uiso 0.50 1 calc PR B 2 C12 C -0.2743(9) 0.2311(6) 0.1425(2) 0.0558(18) Uani 1 1 d . . . H12A H -0.2093 0.2293 0.1763 0.067 Uiso 1 1 calc R B 1 H12B H -0.3706 0.1735 0.1422 0.067 Uiso 1 1 calc R B 1 C13 C -0.0377(8) 0.3772(5) 0.0423(2) 0.0405(14) Uani 1 1 d . . . C14 C 0.0548(9) 0.5175(5) -0.0265(2) 0.0415(15) Uani 1 1 d . . . C15 C 0.0109(9) 0.5543(5) -0.0769(2) 0.0569(17) Uani 1 1 d . B . H15 H -0.0822 0.5174 -0.0959 0.068 Uiso 1 1 calc R . . C16 C 0.1015(9) 0.6445(5) -0.0997(3) 0.0630(18) Uani 1 1 d . . . H16 H 0.0696 0.6684 -0.1337 0.076 Uiso 1 1 calc R B . C17 C 0.2380(10) 0.6983(5) -0.0721(2) 0.0576(18) Uani 1 1 d . B . C18 C 0.2864(10) 0.6618(6) -0.0226(3) 0.0641(19) Uani 1 1 d . . . H18 H 0.3813 0.6984 -0.0041 0.077 Uiso 1 1 calc R B . C19 C 0.1969(9) 0.5718(6) 0.0003(2) 0.0570(18) Uani 1 1 d . B . H19 H 0.2320 0.5473 0.0340 0.068 Uiso 1 1 calc R . . C20 C 0.3039(12) 0.5478(7) 0.2254(4) 0.101(3) Uani 1 1 d . . . H20A H 0.2176 0.5743 0.2524 0.121 Uiso 1 1 calc R . . H20B H 0.4162 0.5213 0.2431 0.121 Uiso 1 1 calc R . . C21 C 0.3489(17) 0.6371(7) 0.1904(4) 0.146(5) Uani 1 1 d . . . H21A H 0.3958 0.6067 0.1576 0.220 Uiso 1 1 calc R . . H21B H 0.4425 0.6843 0.2063 0.220 Uiso 1 1 calc R . . H21C H 0.2390 0.6811 0.1834 0.220 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1170(7) 0.0679(5) 0.0941(6) 0.0168(5) 0.0049(6) -0.0375(5) O1 0.073(3) 0.067(3) 0.064(3) -0.015(3) -0.007(2) -0.017(3) O2 0.099(4) 0.115(4) 0.065(3) -0.014(3) -0.033(3) 0.000(4) O3 0.052(3) 0.069(3) 0.046(2) -0.004(2) 0.014(2) 0.009(2) O4 0.059(3) 0.068(3) 0.047(2) 0.012(2) -0.023(2) -0.015(2) N1 0.055(3) 0.063(3) 0.043(3) 0.002(3) -0.020(3) -0.008(3) N2 0.039(3) 0.048(2) 0.032(2) -0.002(2) 0.009(3) -0.003(2) N3 0.045(3) 0.049(3) 0.037(3) 0.006(2) -0.010(2) -0.012(2) C1 0.045(4) 0.076(5) 0.040(4) -0.009(4) 0.008(3) -0.005(4) C2 0.039(3) 0.064(4) 0.053(4) 0.014(3) 0.001(3) -0.001(4) C3 0.039(4) 0.041(4) 0.053(4) 0.007(3) 0.011(3) -0.003(3) C4 0.062(5) 0.055(4) 0.085(5) 0.006(4) 0.014(4) 0.003(4) C5 0.069(6) 0.071(5) 0.121(7) 0.047(6) 0.008(5) 0.015(5) C6 0.074(7) 0.112(8) 0.100(7) 0.058(6) -0.014(5) -0.002(5) C7 0.056(5) 0.107(6) 0.065(5) 0.019(5) -0.014(4) -0.008(4) C8 0.040(3) 0.038(3) 0.043(3) 0.003(3) 0.007(3) -0.015(3) C9 0.035(4) 0.052(4) 0.032(3) -0.005(3) 0.002(3) -0.006(3) C10 0.051(4) 0.060(4) 0.070(5) 0.012(4) 0.014(4) 0.005(4) C11 0.030(8) 0.078(11) 0.077(11) -0.018(9) 0.016(8) -0.009(8) C11' 0.032(8) 0.110(13) 0.048(9) 0.010(9) 0.018(7) 0.021(8) C12 0.043(4) 0.085(5) 0.040(4) 0.005(4) 0.011(3) 0.000(4) C13 0.048(4) 0.044(3) 0.030(3) -0.003(3) -0.002(3) 0.006(3) C14 0.049(4) 0.044(3) 0.032(3) -0.002(3) -0.001(3) -0.009(3) C15 0.063(4) 0.053(4) 0.055(4) 0.002(3) -0.012(3) -0.016(4) C16 0.079(5) 0.059(4) 0.051(4) 0.015(4) -0.013(4) -0.008(4) C17 0.081(5) 0.044(4) 0.048(4) 0.002(3) 0.010(4) -0.010(3) C18 0.067(5) 0.065(5) 0.060(4) -0.007(4) -0.001(4) -0.021(4) C19 0.055(4) 0.070(4) 0.046(4) 0.007(3) -0.006(3) -0.013(4) C20 0.073(6) 0.097(7) 0.133(7) -0.057(6) 0.015(5) -0.039(5) C21 0.157(10) 0.057(5) 0.225(12) 0.015(7) -0.111(10) -0.026(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C17 1.903(6) . ? O1 C1 1.333(7) . ? O1 C20 1.434(8) . ? O2 C1 1.186(7) . ? O3 C8 1.225(6) . ? O4 C13 1.226(6) . ? N1 C1 1.359(7) . ? N1 C2 1.415(7) . ? N1 H1 0.8600 . ? N2 C8 1.340(7) . ? N2 C9 1.460(6) . ? N2 C12 1.465(7) . ? N3 C13 1.335(6) . ? N3 C14 1.420(7) . ? N3 H3 0.8600 . ? C2 C7 1.390(8) . ? C2 C3 1.390(8) . ? C3 C4 1.378(8) . ? C3 C8 1.498(8) . ? C4 C5 1.355(9) . ? C4 H4 0.9300 . ? C5 C6 1.351(11) . ? C5 H5 0.9300 . ? C6 C7 1.394(10) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 C13 1.519(8) . ? C9 C10 1.539(8) . ? C9 H9 0.9800 . ? C10 C11 1.454(15) . ? C10 C11' 1.514(15) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.590(15) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11' C12 1.446(13) . ? C11' H11C 0.9700 . ? C11' H11D 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 C15 1.377(7) . ? C14 C19 1.380(8) . ? C15 C16 1.375(8) . ? C15 H15 0.9300 . ? C16 C17 1.358(8) . ? C16 H16 0.9300 . ? C17 C18 1.363(8) . ? C18 C19 1.371(8) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.415(11) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 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 O1 C20 117.1(6) . . ? C1 N1 C2 127.2(6) . . ? C1 N1 H1 116.4 . . ? C2 N1 H1 116.4 . . ? C8 N2 C9 120.0(4) . . ? C8 N2 C12 127.2(5) . . ? C9 N2 C12 112.7(4) . . ? C13 N3 C14 129.1(5) . . ? C13 N3 H3 115.4 . . ? C14 N3 H3 115.4 . . ? O2 C1 O1 124.2(7) . . ? O2 C1 N1 127.7(7) . . ? O1 C1 N1 108.2(6) . . ? C7 C2 C3 118.9(6) . . ? C7 C2 N1 122.4(6) . . ? C3 C2 N1 118.7(5) . . ? C4 C3 C2 119.2(6) . . ? C4 C3 C8 119.8(6) . . ? C2 C3 C8 120.9(5) . . ? C5 C4 C3 121.3(7) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C6 C5 C4 120.7(8) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 119.7(8) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C2 C7 C6 120.1(8) . . ? C2 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? O3 C8 N2 122.3(5) . . ? O3 C8 C3 120.9(5) . . ? N2 C8 C3 116.8(5) . . ? N2 C9 C13 111.2(4) . . ? N2 C9 C10 103.7(4) . . ? C13 C9 C10 110.7(5) . . ? N2 C9 H9 110.4 . . ? C13 C9 H9 110.4 . . ? C10 C9 H9 110.4 . . ? C11 C10 C9 104.5(8) . . ? C11' C10 C9 103.7(7) . . ? C11 C10 H10A 110.9 . . ? C11' C10 H10A 141.1 . . ? C9 C10 H10A 110.9 . . ? C11 C10 H10B 110.9 . . ? C11' C10 H10B 73.2 . . ? C9 C10 H10B 110.9 . . ? H10A C10 H10B 108.9 . . ? C10 C11 C12 103.5(9) . . ? C10 C11 H11A 111.1 . . ? C12 C11 H11A 111.1 . . ? C10 C11 H11B 111.1 . . ? C12 C11 H11B 111.1 . . ? H11A C11 H11B 109.0 . . ? C12 C11' C10 107.8(9) . . ? C12 C11' H11C 110.1 . . ? C10 C11' H11C 110.1 . . ? C12 C11' H11D 110.1 . . ? C10 C11' H11D 110.1 . . ? H11C C11' H11D 108.5 . . ? C11' C12 N2 103.1(6) . . ? N2 C12 C11 99.6(6) . . ? C11' C12 H12A 139.4 . . ? N2 C12 H12A 111.8 . . ? C11 C12 H12A 111.8 . . ? C11' C12 H12B 74.0 . . ? N2 C12 H12B 111.8 . . ? C11 C12 H12B 111.8 . . ? H12A C12 H12B 109.6 . . ? O4 C13 N3 125.1(5) . . ? O4 C13 C9 121.4(5) . . ? N3 C13 C9 113.4(5) . . ? C15 C14 C19 118.1(6) . . ? C15 C14 N3 117.7(5) . . ? C19 C14 N3 124.2(5) . . ? C16 C15 C14 121.5(6) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C17 C16 C15 119.4(6) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 120.2(6) . . ? C16 C17 Br1 119.9(5) . . ? C18 C17 Br1 120.0(5) . . ? C17 C18 C19 120.7(6) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C18 C19 C14 120.1(6) . . ? C18 C19 H19 119.9 . . ? C14 C19 H19 119.9 . . ? C21 C20 O1 109.5(7) . . ? C21 C20 H20A 109.8 . . ? O1 C20 H20A 109.8 . . ? C21 C20 H20B 109.8 . . ? O1 C20 H20B 109.8 . . ? H20A C20 H20B 108.2 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C20 O1 C1 O2 0.8(10) . . . . ? C20 O1 C1 N1 -178.8(5) . . . . ? C2 N1 C1 O2 -1.1(11) . . . . ? C2 N1 C1 O1 178.5(6) . . . . ? C1 N1 C2 C7 7.3(11) . . . . ? C1 N1 C2 C3 -172.3(6) . . . . ? C7 C2 C3 C4 -0.7(9) . . . . ? N1 C2 C3 C4 179.0(6) . . . . ? C7 C2 C3 C8 -178.4(6) . . . . ? N1 C2 C3 C8 1.3(9) . . . . ? C2 C3 C4 C5 0.3(10) . . . . ? C8 C3 C4 C5 178.0(6) . . . . ? C3 C4 C5 C6 -0.5(12) . . . . ? C4 C5 C6 C7 1.0(13) . . . . ? C3 C2 C7 C6 1.2(11) . . . . ? N1 C2 C7 C6 -178.4(7) . . . . ? C5 C6 C7 C2 -1.4(13) . . . . ? C9 N2 C8 O3 -9.7(8) . . . . ? C12 N2 C8 O3 174.6(5) . . . . ? C9 N2 C8 C3 168.5(4) . . . . ? C12 N2 C8 C3 -7.2(8) . . . . ? C4 C3 C8 O3 -69.5(7) . . . . ? C2 C3 C8 O3 108.2(7) . . . . ? C4 C3 C8 N2 112.3(6) . . . . ? C2 C3 C8 N2 -70.0(7) . . . . ? C8 N2 C9 C13 -58.7(6) . . . . ? C12 N2 C9 C13 117.5(5) . . . . ? C8 N2 C9 C10 -177.7(5) . . . . ? C12 N2 C9 C10 -1.4(6) . . . . ? N2 C9 C10 C11 26.2(8) . . . . ? C13 C9 C10 C11 -93.2(8) . . . . ? N2 C9 C10 C11' -16.3(9) . . . . ? C13 C9 C10 C11' -135.6(8) . . . . ? C11' C10 C11 C12 55.2(10) . . . . ? C9 C10 C11 C12 -39.2(10) . . . . ? C11 C10 C11' C12 -67.1(14) . . . . ? C9 C10 C11' C12 29.2(13) . . . . ? C10 C11' C12 N2 -29.6(12) . . . . ? C10 C11' C12 C11 59.8(12) . . . . ? C8 N2 C12 C11' -164.8(9) . . . . ? C9 N2 C12 C11' 19.3(10) . . . . ? C8 N2 C12 C11 154.7(7) . . . . ? C9 N2 C12 C11 -21.2(8) . . . . ? C10 C11 C12 C11' -61.8(12) . . . . ? C10 C11 C12 N2 37.1(10) . . . . ? C14 N3 C13 O4 -3.6(9) . . . . ? C14 N3 C13 C9 172.8(5) . . . . ? N2 C9 C13 O4 -19.1(7) . . . . ? C10 C9 C13 O4 95.6(6) . . . . ? N2 C9 C13 N3 164.3(4) . . . . ? C10 C9 C13 N3 -81.0(6) . . . . ? C13 N3 C14 C15 -179.7(6) . . . . ? C13 N3 C14 C19 -1.0(9) . . . . ? C19 C14 C15 C16 -1.8(9) . . . . ? N3 C14 C15 C16 177.1(6) . . . . ? C14 C15 C16 C17 0.3(10) . . . . ? C15 C16 C17 C18 1.1(10) . . . . ? C15 C16 C17 Br1 -179.2(5) . . . . ? C16 C17 C18 C19 -0.9(10) . . . . ? Br1 C17 C18 C19 179.3(5) . . . . ? C17 C18 C19 C14 -0.6(10) . . . . ? C15 C14 C19 C18 1.9(9) . . . . ? N3 C14 C19 C18 -176.8(6) . . . . ? C1 O1 C20 C21 154.3(8) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.535 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 874040' ####################################################################### # # 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_4 #TrackingRef '10447_web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1333099354.peptide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H17 Br F3 N3 O3' _chemical_formula_sum 'C20 H17 Br F3 N3 O3' _chemical_formula_weight 484.28 _chemical_absolute_configuration syn 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.016(5) _cell_length_b 7.612(3) _cell_length_c 12.920(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.130(7) _cell_angle_gamma 90.00 _cell_volume 1059.2(7) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1176 _cell_measurement_theta_min 2.206 _cell_measurement_theta_max 19.443 _exptl_crystal_description 'thin plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 1.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4493 _exptl_absorpt_correction_T_max 0.9707 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5304 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0870 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3444 _reflns_number_gt 2218 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0025P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.017(12) _refine_ls_number_reflns 3444 _refine_ls_number_parameters 316 _refine_ls_number_restraints 59 _refine_ls_R_factor_all 0.0887 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.36307(5) 1.02144(11) -0.20736(5) 0.0998(3) Uani 1 1 d . . . O1 O 1.0332(15) 0.9929(15) 0.5082(6) 0.099(4) Uani 0.70 1 d PDU A 1 O1' O 1.050(3) 0.901(4) 0.5181(11) 0.099(8) Uani 0.30 1 d PDU A 2 O2 O 1.1581(3) 0.7857(5) 0.1061(3) 0.0693(10) Uani 1 1 d . A . O3 O 0.9048(3) 0.7619(5) 0.1479(3) 0.0722(11) Uani 1 1 d . . . N1 N 1.0647(4) 0.8554(5) 0.3546(3) 0.0556(11) Uani 1 1 d . A . H1 H 1.0232 0.8184 0.2947 0.067 Uiso 1 1 calc R . . N2 N 1.1078(3) 0.5549(6) 0.1969(3) 0.0475(10) Uani 1 1 d . A . N3 N 0.8243(3) 0.6149(6) -0.0040(3) 0.0541(11) Uani 1 1 d . . . H3 H 0.8381 0.5271 -0.0419 0.065 Uiso 1 1 calc R . . C1 C 0.9992(5) 0.9138(8) 0.4241(5) 0.0706(17) Uani 1 1 d D . . C2 C 1.1954(5) 0.8489(7) 0.3706(4) 0.0550(13) Uani 1 1 d . . . C3 C 1.2482(5) 0.7737(7) 0.2913(4) 0.0532(13) Uani 1 1 d . A . C4 C 1.3757(5) 0.7692(8) 0.3038(5) 0.0713(16) Uani 1 1 d . . . H4 H 1.4106 0.7207 0.2508 0.086 Uiso 1 1 calc R A . C5 C 1.4507(6) 0.8345(10) 0.3921(6) 0.091(2) Uani 1 1 d . A . H5 H 1.5364 0.8293 0.3997 0.110 Uiso 1 1 calc R . . C6 C 1.4004(6) 0.9077(10) 0.4697(6) 0.098(2) Uani 1 1 d . . . H6 H 1.4525 0.9526 0.5300 0.118 Uiso 1 1 calc R A . C7 C 1.2742(5) 0.9161(8) 0.4602(5) 0.0796(17) Uani 1 1 d . A . H7 H 1.2413 0.9668 0.5137 0.096 Uiso 1 1 calc R . . C8 C 1.1692(4) 0.7046(7) 0.1910(4) 0.0517(13) Uani 1 1 d . . . C9 C 1.0075(4) 0.4960(7) 0.1118(3) 0.0473(12) Uani 1 1 d . . . H9 H 1.0395 0.4685 0.0484 0.057 Uiso 1 1 calc R A . C10 C 0.9605(5) 0.3293(7) 0.1564(5) 0.0680(17) Uani 1 1 d . A . H10A H 0.8851 0.3527 0.1815 0.082 Uiso 1 1 calc R B 1 H10B H 0.9440 0.2379 0.1030 0.082 Uiso 1 1 calc R B 1 C11 C 1.0638(9) 0.2755(13) 0.2465(7) 0.075(2) Uani 0.70 1 d P A 1 H11A H 1.0311 0.2130 0.3001 0.089 Uiso 0.70 1 calc PR A 1 H11B H 1.1225 0.2000 0.2214 0.089 Uiso 0.70 1 calc PR A 1 C11' C 0.9856(18) 0.349(3) 0.2652(16) 0.061(5) Uani 0.30 1 d P A 2 H11C H 0.9868 0.2370 0.3007 0.073 Uiso 0.30 1 calc PR A 2 H11D H 0.9249 0.4252 0.2873 0.073 Uiso 0.30 1 calc PR A 2 C12 C 1.1241(5) 0.4406(7) 0.2897(4) 0.0642(15) Uani 1 1 d . . . H12A H 1.0840 0.4896 0.3432 0.077 Uiso 1 1 calc R A 1 H12B H 1.2114 0.4223 0.3203 0.077 Uiso 1 1 calc R A 1 C13 C 0.9076(5) 0.6394(7) 0.0873(4) 0.0516(13) Uani 1 1 d . A . C14 C 0.7191(4) 0.7133(7) -0.0449(4) 0.0518(13) Uani 1 1 d . . . C15 C 0.6425(5) 0.6538(9) -0.1354(5) 0.0790(18) Uani 1 1 d . . . H15 H 0.6621 0.5491 -0.1652 0.095 Uiso 1 1 calc R . . C16 C 0.5365(5) 0.7446(10) -0.1842(5) 0.088(2) Uani 1 1 d . . . H16 H 0.4866 0.7016 -0.2461 0.106 Uiso 1 1 calc R . . C17 C 0.5068(5) 0.8954(9) -0.1411(5) 0.0684(16) Uani 1 1 d . . . C18 C 0.5824(5) 0.9618(8) -0.0519(4) 0.0768(18) Uani 1 1 d . . . H18 H 0.5623 1.0677 -0.0237 0.092 Uiso 1 1 calc R . . C19 C 0.6894(5) 0.8715(8) -0.0032(4) 0.0728(17) Uani 1 1 d . . . H19 H 0.7407 0.9174 0.0572 0.087 Uiso 1 1 calc R . . C20 C 0.8579(6) 0.9138(9) 0.3818(5) 0.091(2) Uani 1 1 d D A . F1 F 0.8193(4) 1.0093(10) 0.2945(4) 0.0891(14) Uani 0.70 1 d PDU A 1 F2 F 0.7956(7) 0.9672(18) 0.4541(6) 0.135(4) Uani 0.70 1 d PDU A 1 F3 F 0.8188(10) 0.7507(9) 0.3557(6) 0.108(3) Uani 0.70 1 d PDU A 1 F4 F 0.8231(18) 1.0729(17) 0.403(2) 0.150(6) Uani 0.30 1 d PDU A 2 F5 F 0.8157(14) 0.827(2) 0.4596(12) 0.097(4) Uani 0.30 1 d PDU A 2 F6 F 0.807(2) 0.799(2) 0.3093(13) 0.126(6) Uani 0.30 1 d PDU A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0624(3) 0.1285(6) 0.1086(5) 0.0263(5) 0.0182(3) 0.0340(5) O1 0.082(6) 0.135(11) 0.085(5) -0.070(6) 0.026(4) -0.019(9) O1' 0.084(11) 0.14(2) 0.072(11) -0.064(11) 0.025(8) -0.007(17) O2 0.089(3) 0.063(2) 0.055(2) 0.014(2) 0.014(2) -0.008(2) O3 0.071(2) 0.079(3) 0.062(3) -0.024(2) 0.0049(19) 0.022(2) N1 0.063(3) 0.056(3) 0.048(3) -0.010(2) 0.012(2) -0.010(2) N2 0.058(2) 0.047(3) 0.039(2) 0.010(2) 0.0135(18) -0.001(2) N3 0.057(2) 0.061(3) 0.041(3) -0.010(2) 0.002(2) 0.013(2) C1 0.081(4) 0.080(4) 0.053(4) -0.020(4) 0.017(3) -0.025(3) C2 0.060(3) 0.051(3) 0.053(3) -0.004(3) 0.009(3) -0.004(3) C3 0.061(3) 0.051(3) 0.044(3) 0.007(3) 0.005(3) -0.003(3) C4 0.064(4) 0.071(4) 0.078(4) 0.002(4) 0.014(3) 0.006(3) C5 0.058(4) 0.109(6) 0.098(5) 0.000(5) -0.003(4) -0.009(4) C6 0.076(5) 0.107(5) 0.097(5) -0.019(4) -0.014(4) -0.016(4) C7 0.071(4) 0.089(4) 0.071(4) -0.022(3) -0.001(3) -0.008(3) C8 0.058(3) 0.051(4) 0.049(4) 0.011(3) 0.017(3) 0.012(3) C9 0.059(3) 0.046(3) 0.039(3) -0.001(3) 0.014(2) 0.003(3) C10 0.080(4) 0.056(4) 0.072(5) 0.004(3) 0.024(4) -0.008(3) C11 0.098(7) 0.059(6) 0.067(6) 0.025(5) 0.017(6) 0.005(6) C11' 0.083(14) 0.036(11) 0.074(16) 0.028(11) 0.042(12) 0.005(10) C12 0.079(4) 0.059(4) 0.054(3) 0.015(3) 0.013(3) 0.001(3) C13 0.065(3) 0.048(3) 0.046(4) 0.000(3) 0.023(3) 0.004(3) C14 0.053(3) 0.054(4) 0.049(3) 0.000(3) 0.014(3) 0.012(3) C15 0.075(4) 0.079(4) 0.074(4) -0.021(4) -0.007(3) 0.021(3) C16 0.064(4) 0.108(6) 0.083(5) -0.018(4) -0.008(3) 0.010(4) C17 0.061(4) 0.076(5) 0.069(4) 0.008(3) 0.018(3) 0.014(3) C18 0.080(4) 0.075(5) 0.074(4) -0.008(3) 0.012(3) 0.022(3) C19 0.067(4) 0.081(5) 0.068(4) -0.015(3) 0.006(3) 0.019(3) C20 0.071(5) 0.118(7) 0.096(6) -0.054(6) 0.046(4) -0.032(5) F1 0.074(3) 0.109(4) 0.081(3) 0.010(4) 0.011(3) 0.011(4) F2 0.094(4) 0.220(10) 0.099(5) -0.062(7) 0.037(4) 0.009(7) F3 0.105(4) 0.108(5) 0.092(6) 0.014(4) -0.020(5) -0.049(4) F4 0.117(10) 0.146(13) 0.187(14) 0.012(12) 0.030(10) 0.030(10) F5 0.082(8) 0.116(11) 0.105(9) -0.001(9) 0.049(7) -0.020(8) F6 0.109(10) 0.187(13) 0.074(11) -0.014(11) -0.001(10) -0.010(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C17 1.895(5) . ? O1 C1 1.230(7) . ? O1' C1 1.232(10) . ? O2 C8 1.242(5) . ? O3 C13 1.222(6) . ? N1 C1 1.340(6) . ? N1 C2 1.412(6) . ? N1 H1 0.8600 . ? N2 C8 1.335(6) . ? N2 C9 1.457(5) . ? N2 C12 1.461(6) . ? N3 C13 1.347(6) . ? N3 C14 1.388(6) . ? N3 H3 0.8600 . ? C1 C20 1.537(9) . ? C2 C7 1.390(7) . ? C2 C3 1.401(6) . ? C3 C4 1.380(6) . ? C3 C8 1.497(7) . ? C4 C5 1.354(7) . ? C4 H4 0.9300 . ? C5 C6 1.362(8) . ? C5 H5 0.9300 . ? C6 C7 1.371(8) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 C10 1.528(7) . ? C9 C13 1.535(7) . ? C9 H9 0.9800 . ? C10 C11' 1.383(19) . ? C10 C11 1.503(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.476(10) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11' C12 1.645(18) . ? C11' H11C 0.9700 . ? C11' H11D 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 C15 1.367(7) . ? C14 C19 1.386(7) . ? C15 C16 1.389(8) . ? C15 H15 0.9300 . ? C16 C17 1.346(8) . ? C16 H16 0.9300 . ? C17 C18 1.369(7) . ? C18 C19 1.395(7) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 F4 1.316(8) . ? C20 F6 1.317(8) . ? C20 F2 1.334(6) . ? C20 F3 1.334(7) . ? C20 F1 1.335(6) . ? C20 F5 1.362(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 126.2(4) . . ? C1 N1 H1 116.9 . . ? C2 N1 H1 116.9 . . ? C8 N2 C9 122.2(4) . . ? C8 N2 C12 125.3(4) . . ? C9 N2 C12 112.3(4) . . ? C13 N3 C14 128.3(4) . . ? C13 N3 H3 115.9 . . ? C14 N3 H3 115.9 . . ? O1 C1 N1 130.3(9) . . ? O1' C1 N1 115.8(17) . . ? O1 C1 C20 114.3(9) . . ? O1' C1 C20 125(2) . . ? N1 C1 C20 114.2(5) . . ? C7 C2 C3 118.4(5) . . ? C7 C2 N1 123.2(5) . . ? C3 C2 N1 118.3(4) . . ? C4 C3 C2 119.5(5) . . ? C4 C3 C8 119.0(5) . . ? C2 C3 C8 121.4(4) . . ? C5 C4 C3 121.0(6) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 120.0(6) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C7 121.0(6) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C2 120.1(6) . . ? C6 C7 H7 120.0 . . ? C2 C7 H7 120.0 . . ? O2 C8 N2 121.2(5) . . ? O2 C8 C3 121.4(5) . . ? N2 C8 C3 117.4(5) . . ? N2 C9 C10 103.5(4) . . ? N2 C9 C13 109.5(4) . . ? C10 C9 C13 112.6(4) . . ? N2 C9 H9 110.4 . . ? C10 C9 H9 110.4 . . ? C13 C9 H9 110.4 . . ? C11' C10 C9 106.3(8) . . ? C11 C10 C9 104.9(5) . . ? C11' C10 H10A 69.1 . . ? C11 C10 H10A 110.8 . . ? C9 C10 H10A 110.8 . . ? C11' C10 H10B 140.4 . . ? C11 C10 H10B 110.8 . . ? C9 C10 H10B 110.8 . . ? H10A C10 H10B 108.8 . . ? C12 C11 C10 105.6(6) . . ? C12 C11 H11A 110.6 . . ? C10 C11 H11A 110.6 . . ? C12 C11 H11B 110.6 . . ? C10 C11 H11B 110.6 . . ? H11A C11 H11B 108.8 . . ? C10 C11' C12 102.8(11) . . ? C10 C11' H11C 111.2 . . ? C12 C11' H11C 111.2 . . ? C10 C11' H11D 111.2 . . ? C12 C11' H11D 111.2 . . ? H11C C11' H11D 109.1 . . ? N2 C12 C11 103.2(5) . . ? N2 C12 C11' 98.3(7) . . ? N2 C12 H12A 111.1 . . ? C11 C12 H12A 111.1 . . ? C11' C12 H12A 75.9 . . ? N2 C12 H12B 111.1 . . ? C11 C12 H12B 111.1 . . ? C11' C12 H12B 144.8 . . ? H12A C12 H12B 109.1 . . ? O3 C13 N3 124.2(5) . . ? O3 C13 C9 121.6(5) . . ? N3 C13 C9 114.1(5) . . ? C15 C14 C19 117.8(5) . . ? C15 C14 N3 117.5(5) . . ? C19 C14 N3 124.6(5) . . ? C14 C15 C16 122.1(6) . . ? C14 C15 H15 118.9 . . ? C16 C15 H15 118.9 . . ? C17 C16 C15 119.4(6) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 120.4(5) . . ? C16 C17 Br1 119.9(5) . . ? C18 C17 Br1 119.7(5) . . ? C17 C18 C19 120.3(6) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C14 C19 C18 119.9(5) . . ? C14 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? F4 C20 F6 131.4(17) . . ? F4 C20 F2 50.0(9) . . ? F6 C20 F2 119.8(14) . . ? F4 C20 F3 144.7(12) . . ? F2 C20 F3 105.9(9) . . ? F4 C20 F1 67.8(12) . . ? F6 C20 F1 75.3(11) . . ? F2 C20 F1 107.9(8) . . ? F3 C20 F1 105.3(7) . . ? F4 C20 F5 97.5(12) . . ? F6 C20 F5 92.6(13) . . ? F2 C20 F5 47.6(7) . . ? F3 C20 F5 66.1(10) . . ? F1 C20 F5 142.1(9) . . ? F4 C20 C1 104.1(11) . . ? F6 C20 C1 119.9(14) . . ? F2 C20 C1 112.5(6) . . ? F3 C20 C1 109.8(7) . . ? F1 C20 C1 114.8(5) . . ? F5 C20 C1 102.4(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 10.3(13) . . . . ? C2 N1 C1 O1' -27(2) . . . . ? C2 N1 C1 C20 176.9(5) . . . . ? C1 N1 C2 C7 -4.9(8) . . . . ? C1 N1 C2 C3 176.2(5) . . . . ? C7 C2 C3 C4 -0.4(7) . . . . ? N1 C2 C3 C4 178.6(5) . . . . ? C7 C2 C3 C8 -177.8(5) . . . . ? N1 C2 C3 C8 1.2(7) . . . . ? C2 C3 C4 C5 0.8(8) . . . . ? C8 C3 C4 C5 178.3(5) . . . . ? C3 C4 C5 C6 -0.7(10) . . . . ? C4 C5 C6 C7 0.2(11) . . . . ? C5 C6 C7 C2 0.2(10) . . . . ? C3 C2 C7 C6 -0.1(9) . . . . ? N1 C2 C7 C6 -179.0(6) . . . . ? C9 N2 C8 O2 -12.3(7) . . . . ? C12 N2 C8 O2 173.3(4) . . . . ? C9 N2 C8 C3 165.7(4) . . . . ? C12 N2 C8 C3 -8.7(7) . . . . ? C4 C3 C8 O2 -72.2(6) . . . . ? C2 C3 C8 O2 105.2(6) . . . . ? C4 C3 C8 N2 109.9(6) . . . . ? C2 C3 C8 N2 -72.7(6) . . . . ? C8 N2 C9 C10 -176.2(4) . . . . ? C12 N2 C9 C10 -1.1(5) . . . . ? C8 N2 C9 C13 -55.9(5) . . . . ? C12 N2 C9 C13 119.2(4) . . . . ? N2 C9 C10 C11' 27.9(10) . . . . ? C13 C9 C10 C11' -90.3(10) . . . . ? N2 C9 C10 C11 -18.4(7) . . . . ? C13 C9 C10 C11 -136.5(6) . . . . ? C11' C10 C11 C12 -66.8(12) . . . . ? C9 C10 C11 C12 31.4(8) . . . . ? C11 C10 C11' C12 54.5(10) . . . . ? C9 C10 C11' C12 -40.4(13) . . . . ? C8 N2 C12 C11 -164.8(6) . . . . ? C9 N2 C12 C11 20.4(7) . . . . ? C8 N2 C12 C11' 154.0(8) . . . . ? C9 N2 C12 C11' -20.8(9) . . . . ? C10 C11 C12 N2 -31.3(8) . . . . ? C10 C11 C12 C11' 56.0(11) . . . . ? C10 C11' C12 N2 37.7(12) . . . . ? C10 C11' C12 C11 -62.9(12) . . . . ? C14 N3 C13 O3 -3.2(8) . . . . ? C14 N3 C13 C9 175.4(4) . . . . ? N2 C9 C13 O3 -14.7(6) . . . . ? C10 C9 C13 O3 99.8(6) . . . . ? N2 C9 C13 N3 166.6(4) . . . . ? C10 C9 C13 N3 -78.8(5) . . . . ? C13 N3 C14 C15 -174.6(5) . . . . ? C13 N3 C14 C19 8.6(8) . . . . ? C19 C14 C15 C16 -1.3(9) . . . . ? N3 C14 C15 C16 -178.4(5) . . . . ? C14 C15 C16 C17 -0.6(10) . . . . ? C15 C16 C17 C18 2.1(9) . . . . ? C15 C16 C17 Br1 179.6(5) . . . . ? C16 C17 C18 C19 -1.7(9) . . . . ? Br1 C17 C18 C19 -179.1(4) . . . . ? C15 C14 C19 C18 1.8(8) . . . . ? N3 C14 C19 C18 178.6(5) . . . . ? C17 C18 C19 C14 -0.3(8) . . . . ? O1 C1 C20 F4 38.9(16) . . . . ? O1' C1 C20 F4 77(2) . . . . ? N1 C1 C20 F4 -129.9(13) . . . . ? O1 C1 C20 F6 -162.6(15) . . . . ? O1' C1 C20 F6 -125(2) . . . . ? N1 C1 C20 F6 28.6(15) . . . . ? O1 C1 C20 F2 -13.2(13) . . . . ? O1' C1 C20 F2 24.8(19) . . . . ? N1 C1 C20 F2 177.9(8) . . . . ? O1 C1 C20 F3 -131.0(10) . . . . ? O1' C1 C20 F3 -92.9(17) . . . . ? N1 C1 C20 F3 60.2(8) . . . . ? O1 C1 C20 F1 110.7(9) . . . . ? O1' C1 C20 F1 148.7(17) . . . . ? N1 C1 C20 F1 -58.2(7) . . . . ? O1 C1 C20 F5 -62.2(13) . . . . ? O1' C1 C20 F5 -24.2(19) . . . . ? N1 C1 C20 F5 129.0(10) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.414 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 874041' ####################################################################### # # 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_5 #TrackingRef '10447_web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1333099354.peptide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H26 Br N3 O4' _chemical_formula_sum 'C23 H26 Br N3 O4' _chemical_formula_weight 488.38 _chemical_absolute_configuration syn 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.8420(19) _cell_length_b 7.0231(10) _cell_length_c 13.3863(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.547(3) _cell_angle_gamma 90.00 _cell_volume 1207.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1681 _cell_measurement_theta_min 2.208 _cell_measurement_theta_max 27.924 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 1.734 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4117 _exptl_absorpt_correction_T_max 0.8321 _exptl_absorpt_process_details "Bruker's sadabs" _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9259 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.1038 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4152 _reflns_number_gt 2476 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0373P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.050(17) _refine_ls_number_reflns 4152 _refine_ls_number_parameters 282 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1592 _refine_ls_R_factor_gt 0.1045 _refine_ls_wR_factor_ref 0.1533 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 1.203 _refine_ls_restrained_S_all 1.203 _refine_ls_shift/su_max 0.031 _refine_ls_shift/su_mean 0.001 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 Br Br 0.45382(9) 0.6993(2) 1.14003(8) 0.1429(6) Uani 1 1 d . . . O1 O 0.9758(5) 0.7790(9) 0.5028(4) 0.107(2) Uani 1 1 d . . . O2 O 1.1115(4) 0.9614(7) 0.9117(3) 0.0673(14) Uani 1 1 d . . . O3 O 0.8819(4) 0.9587(7) 0.8476(3) 0.0736(16) Uani 1 1 d . . . O4 O 0.8503(5) 0.8589(7) 0.6082(3) 0.0773(15) Uani 1 1 d . . . N1 N 1.0102(5) 0.8814(7) 0.6629(4) 0.0609(16) Uani 1 1 d . . . H1 H 0.9789 0.9081 0.7177 0.073 Uiso 1 1 calc R . . N2 N 1.0469(4) 1.1984(9) 0.8184(3) 0.0520(13) Uani 1 1 d . . . N3 N 0.8412(4) 1.1025(8) 0.9954(4) 0.0582(15) Uani 1 1 d . . . H3 H 0.8624 1.1891 1.0363 0.070 Uiso 1 1 calc R . . C1 C 0.9507(7) 0.8358(10) 0.5841(6) 0.065(2) Uani 1 1 d . . . C2 C 1.1192(6) 0.8897(10) 0.6642(5) 0.0609(19) Uani 1 1 d . . . C3 C 1.1694(6) 0.9764(9) 0.7435(5) 0.0555(18) Uani 1 1 d . . . C4 C 1.2749(7) 0.9889(12) 0.7485(6) 0.075(2) Uani 1 1 d . . . H4 H 1.3062 1.0481 0.8032 0.090 Uiso 1 1 calc R . . C5 C 1.3353(7) 0.9167(15) 0.6755(8) 0.100(3) Uani 1 1 d . . . H5 H 1.4074 0.9288 0.6782 0.120 Uiso 1 1 calc R . . C6 C 1.2856(9) 0.8230(13) 0.5957(7) 0.097(3) Uani 1 1 d . . . H6 H 1.3263 0.7700 0.5458 0.116 Uiso 1 1 calc R . . C7 C 1.1801(8) 0.8066(11) 0.5884(6) 0.085(3) Uani 1 1 d . . . H7 H 1.1491 0.7424 0.5352 0.103 Uiso 1 1 calc R . . C8 C 1.1075(6) 1.0444(9) 0.8305(5) 0.0523(19) Uani 1 1 d . . . C9 C 0.9693(5) 1.2496(9) 0.8927(4) 0.0528(18) Uani 1 1 d . . . H9 H 1.0035 1.2845 0.9559 0.063 Uiso 1 1 calc R . . C10 C 0.9150(7) 1.4230(10) 0.8468(5) 0.077(2) Uani 1 1 d . . . H10A H 0.8412 1.4229 0.8614 0.092 Uiso 1 1 calc R . . H10B H 0.9457 1.5406 0.8712 0.092 Uiso 1 1 calc R . . C11 C 0.9331(8) 1.3988(14) 0.7382(6) 0.110(3) Uani 1 1 d . . . H11A H 0.8832 1.3103 0.7094 0.132 Uiso 1 1 calc R . . H11B H 0.9269 1.5198 0.7037 0.132 Uiso 1 1 calc R . . C12 C 1.0396(7) 1.3236(10) 0.7303(5) 0.073(2) Uani 1 1 d . . . H12A H 1.0908 1.4249 0.7335 0.087 Uiso 1 1 calc R . . H12B H 1.0485 1.2525 0.6688 0.087 Uiso 1 1 calc R . . C13 C 0.8952(5) 1.0847(10) 0.9086(5) 0.0522(18) Uani 1 1 d . . . C14 C 0.7545(6) 0.9946(10) 1.0255(5) 0.0582(19) Uani 1 1 d . . . C15 C 0.7032(7) 1.0589(13) 1.1102(6) 0.088(3) Uani 1 1 d . . . H15 H 0.7297 1.1630 1.1449 0.106 Uiso 1 1 calc R . . C16 C 0.6146(7) 0.9723(15) 1.1433(6) 0.098(3) Uani 1 1 d . . . H16 H 0.5812 1.0194 1.1995 0.117 Uiso 1 1 calc R . . C17 C 0.5752(7) 0.8193(14) 1.0954(7) 0.089(3) Uani 1 1 d . . . C18 C 0.6282(7) 0.7484(12) 1.0136(7) 0.086(3) Uani 1 1 d . . . H18 H 0.6031 0.6406 0.9809 0.103 Uiso 1 1 calc R . . C19 C 0.7169(7) 0.8346(11) 0.9802(6) 0.070(2) Uani 1 1 d . . . H19 H 0.7519 0.7834 0.9260 0.083 Uiso 1 1 calc R . . C20 C 0.7726(8) 0.8098(13) 0.5365(6) 0.098(3) Uani 1 1 d . . . H20A H 0.7808 0.6783 0.5159 0.117 Uiso 1 1 calc R . . H20B H 0.7785 0.8904 0.4779 0.117 Uiso 1 1 calc R . . C21 C 0.6699(8) 0.837(2) 0.5833(8) 0.131(4) Uani 1 1 d . . . H21 H 0.6647 0.9682 0.6081 0.157 Uiso 1 1 calc R . . C22 C 0.6549(8) 0.704(3) 0.6668(10) 0.202(6) Uani 1 1 d . . . H22A H 0.6614 0.5757 0.6431 0.302 Uiso 1 1 calc R . . H22B H 0.5869 0.7222 0.6944 0.302 Uiso 1 1 calc R . . H22C H 0.7068 0.7275 0.7175 0.302 Uiso 1 1 calc R . . C23 C 0.5862(9) 0.804(2) 0.5027(11) 0.217(8) Uani 1 1 d . . . H23A H 0.5186 0.8073 0.5326 0.325 Uiso 1 1 calc R . . H23B H 0.5969 0.6827 0.4718 0.325 Uiso 1 1 calc R . . H23C H 0.5906 0.9027 0.4530 0.325 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 Br 0.0999(8) 0.1636(11) 0.1653(10) -0.0001(11) 0.0160(6) -0.0581(9) O1 0.131(5) 0.148(6) 0.044(3) -0.034(4) 0.011(3) -0.004(4) O2 0.097(4) 0.067(3) 0.038(2) 0.015(3) -0.002(2) 0.008(3) O3 0.102(4) 0.062(3) 0.057(3) -0.030(3) 0.010(3) -0.013(3) O4 0.084(4) 0.091(4) 0.057(3) -0.018(3) -0.006(3) -0.010(3) N1 0.090(5) 0.064(4) 0.028(3) -0.018(3) 0.002(3) -0.004(4) N2 0.088(4) 0.039(3) 0.028(3) 0.007(3) 0.008(3) -0.004(4) N3 0.069(4) 0.060(4) 0.045(3) -0.015(3) 0.006(3) -0.013(3) C1 0.092(7) 0.053(5) 0.051(5) 0.003(4) 0.008(5) -0.007(5) C2 0.062(5) 0.062(5) 0.059(5) 0.006(4) 0.010(4) 0.000(4) C3 0.077(6) 0.046(4) 0.044(4) 0.012(4) 0.014(4) -0.012(4) C4 0.080(6) 0.083(6) 0.062(5) 0.009(5) 0.021(5) -0.017(5) C5 0.076(7) 0.113(8) 0.111(7) 0.004(7) 0.004(6) -0.002(6) C6 0.096(8) 0.098(6) 0.098(7) 0.002(6) 0.059(6) 0.007(6) C7 0.093(7) 0.078(6) 0.086(6) -0.020(5) 0.032(6) -0.012(5) C8 0.081(6) 0.045(4) 0.031(4) 0.007(3) -0.014(4) -0.010(4) C9 0.082(5) 0.048(4) 0.028(3) -0.008(3) 0.000(4) 0.002(4) C10 0.115(7) 0.043(4) 0.071(6) 0.007(4) 0.002(5) 0.007(5) C11 0.163(10) 0.106(8) 0.062(6) 0.041(5) 0.011(6) 0.040(7) C12 0.118(7) 0.056(4) 0.045(4) 0.013(4) 0.009(5) 0.002(5) C13 0.061(5) 0.054(5) 0.042(4) 0.005(4) 0.002(4) 0.007(4) C14 0.076(5) 0.051(5) 0.048(4) 0.004(4) 0.001(4) 0.003(4) C15 0.088(7) 0.102(6) 0.074(6) -0.025(5) 0.014(5) -0.023(6) C16 0.089(7) 0.108(7) 0.097(7) -0.024(6) 0.035(6) -0.025(6) C17 0.092(7) 0.074(6) 0.102(7) 0.005(6) -0.003(6) -0.020(6) C18 0.093(6) 0.066(6) 0.099(6) -0.016(5) -0.013(5) -0.025(5) C19 0.085(6) 0.051(4) 0.072(5) -0.012(4) -0.002(4) -0.008(4) C20 0.114(8) 0.103(7) 0.075(5) -0.019(5) -0.026(6) -0.023(6) C21 0.066(7) 0.207(13) 0.119(9) -0.015(9) -0.015(7) -0.015(8) C22 0.106(9) 0.301(19) 0.199(12) 0.050(18) 0.051(8) -0.038(14) C23 0.111(10) 0.28(2) 0.264(15) -0.087(14) -0.023(11) 0.041(11) _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 Br C17 1.875(9) . ? O1 C1 1.206(8) . ? O2 C8 1.234(6) . ? O3 C13 1.215(7) . ? O4 C1 1.342(9) . ? O4 C20 1.421(8) . ? N1 C1 1.336(9) . ? N1 C2 1.401(8) . ? N1 H1 0.8600 . ? N2 C8 1.341(8) . ? N2 C9 1.460(8) . ? N2 C12 1.474(8) . ? N3 C13 1.365(7) . ? N3 C14 1.409(8) . ? N3 H3 0.8600 . ? C2 C3 1.378(9) . ? C2 C7 1.413(10) . ? C3 C4 1.358(9) . ? C3 C8 1.495(9) . ? C4 C5 1.351(11) . ? C4 H4 0.9300 . ? C5 C6 1.403(12) . ? C5 H5 0.9300 . ? C6 C7 1.362(11) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 C13 1.515(9) . ? C9 C10 1.529(9) . ? C9 H9 0.9800 . ? C10 C11 1.485(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.470(10) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 C19 1.363(9) . ? C14 C15 1.392(9) . ? C15 C16 1.368(10) . ? C15 H15 0.9300 . ? C16 C17 1.348(11) . ? C16 H16 0.9300 . ? C17 C18 1.388(11) . ? C18 C19 1.368(10) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.478(12) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.471(15) . ? C21 C23 1.535(13) . ? C21 H21 0.9800 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 O4 C20 118.6(6) . . ? C1 N1 C2 125.7(7) . . ? C1 N1 H1 117.2 . . ? C2 N1 H1 117.2 . . ? C8 N2 C9 121.0(5) . . ? C8 N2 C12 127.6(5) . . ? C9 N2 C12 111.1(6) . . ? C13 N3 C14 127.1(6) . . ? C13 N3 H3 116.5 . . ? C14 N3 H3 116.5 . . ? O1 C1 N1 129.5(9) . . ? O1 C1 O4 121.6(8) . . ? N1 C1 O4 108.9(7) . . ? C3 C2 N1 119.2(7) . . ? C3 C2 C7 118.5(7) . . ? N1 C2 C7 122.3(7) . . ? C4 C3 C2 121.7(7) . . ? C4 C3 C8 118.6(7) . . ? C2 C3 C8 119.5(7) . . ? C5 C4 C3 121.2(8) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 117.8(9) . . ? C4 C5 H5 121.1 . . ? C6 C5 H5 121.1 . . ? C7 C6 C5 122.6(9) . . ? C7 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? C6 C7 C2 118.1(8) . . ? C6 C7 H7 121.0 . . ? C2 C7 H7 121.0 . . ? O2 C8 N2 120.4(6) . . ? O2 C8 C3 121.2(6) . . ? N2 C8 C3 118.4(5) . . ? N2 C9 C13 109.9(5) . . ? N2 C9 C10 103.5(5) . . ? C13 C9 C10 112.4(6) . . ? N2 C9 H9 110.3 . . ? C13 C9 H9 110.3 . . ? C10 C9 H9 110.3 . . ? C11 C10 C9 103.1(6) . . ? C11 C10 H10A 111.1 . . ? C9 C10 H10A 111.1 . . ? C11 C10 H10B 111.1 . . ? C9 C10 H10B 111.1 . . ? H10A C10 H10B 109.1 . . ? C12 C11 C10 105.4(7) . . ? C12 C11 H11A 110.7 . . ? C10 C11 H11A 110.7 . . ? C12 C11 H11B 110.7 . . ? C10 C11 H11B 110.7 . . ? H11A C11 H11B 108.8 . . ? C11 C12 N2 102.1(6) . . ? C11 C12 H12A 111.4 . . ? N2 C12 H12A 111.4 . . ? C11 C12 H12B 111.4 . . ? N2 C12 H12B 111.4 . . ? H12A C12 H12B 109.2 . . ? O3 C13 N3 124.8(7) . . ? O3 C13 C9 123.1(6) . . ? N3 C13 C9 112.0(6) . . ? C19 C14 C15 117.5(8) . . ? C19 C14 N3 126.5(7) . . ? C15 C14 N3 116.1(7) . . ? C16 C15 C14 121.5(8) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C17 C16 C15 120.6(8) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 118.5(8) . . ? C16 C17 Br 121.1(8) . . ? C18 C17 Br 120.4(8) . . ? C19 C18 C17 121.0(8) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C14 C19 C18 120.8(8) . . ? C14 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? O4 C20 C21 107.7(7) . . ? O4 C20 H20A 110.2 . . ? C21 C20 H20A 110.2 . . ? O4 C20 H20B 110.2 . . ? C21 C20 H20B 110.2 . . ? H20A C20 H20B 108.5 . . ? C22 C21 C20 111.3(10) . . ? C22 C21 C23 110.1(12) . . ? C20 C21 C23 107.7(9) . . ? C22 C21 H21 109.3 . . ? C20 C21 H21 109.3 . . ? C23 C21 H21 109.3 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 6.6(12) . . . . ? C2 N1 C1 O4 -174.7(6) . . . . ? C20 O4 C1 O1 1.7(11) . . . . ? C20 O4 C1 N1 -177.2(6) . . . . ? C1 N1 C2 C3 166.5(6) . . . . ? C1 N1 C2 C7 -15.6(11) . . . . ? N1 C2 C3 C4 -179.9(6) . . . . ? C7 C2 C3 C4 2.2(10) . . . . ? N1 C2 C3 C8 5.3(9) . . . . ? C7 C2 C3 C8 -172.6(6) . . . . ? C2 C3 C4 C5 0.1(12) . . . . ? C8 C3 C4 C5 175.0(8) . . . . ? C3 C4 C5 C6 -2.0(13) . . . . ? C4 C5 C6 C7 1.5(14) . . . . ? C5 C6 C7 C2 0.8(13) . . . . ? C3 C2 C7 C6 -2.6(11) . . . . ? N1 C2 C7 C6 179.6(7) . . . . ? C9 N2 C8 O2 -12.4(9) . . . . ? C12 N2 C8 O2 174.2(6) . . . . ? C9 N2 C8 C3 167.6(6) . . . . ? C12 N2 C8 C3 -5.8(9) . . . . ? C4 C3 C8 O2 -66.9(9) . . . . ? C2 C3 C8 O2 108.0(8) . . . . ? C4 C3 C8 N2 113.1(7) . . . . ? C2 C3 C8 N2 -71.9(8) . . . . ? C8 N2 C9 C13 -56.5(7) . . . . ? C12 N2 C9 C13 117.9(6) . . . . ? C8 N2 C9 C10 -176.7(6) . . . . ? C12 N2 C9 C10 -2.3(7) . . . . ? N2 C9 C10 C11 24.2(8) . . . . ? C13 C9 C10 C11 -94.3(8) . . . . ? C9 C10 C11 C12 -38.1(9) . . . . ? C10 C11 C12 N2 36.1(8) . . . . ? C8 N2 C12 C11 153.3(7) . . . . ? C9 N2 C12 C11 -20.6(8) . . . . ? C14 N3 C13 O3 -7.3(10) . . . . ? C14 N3 C13 C9 168.5(6) . . . . ? N2 C9 C13 O3 -21.7(8) . . . . ? C10 C9 C13 O3 93.0(7) . . . . ? N2 C9 C13 N3 162.4(5) . . . . ? C10 C9 C13 N3 -82.8(7) . . . . ? C13 N3 C14 C19 9.9(11) . . . . ? C13 N3 C14 C15 -170.5(6) . . . . ? C19 C14 C15 C16 -4.0(12) . . . . ? N3 C14 C15 C16 176.3(7) . . . . ? C14 C15 C16 C17 1.0(14) . . . . ? C15 C16 C17 C18 1.9(13) . . . . ? C15 C16 C17 Br -180.0(7) . . . . ? C16 C17 C18 C19 -1.9(13) . . . . ? Br C17 C18 C19 180.0(6) . . . . ? C15 C14 C19 C18 4.0(11) . . . . ? N3 C14 C19 C18 -176.3(7) . . . . ? C17 C18 C19 C14 -1.2(12) . . . . ? C1 O4 C20 C21 176.6(8) . . . . ? O4 C20 C21 C22 -65.1(12) . . . . ? O4 C20 C21 C23 174.2(10) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.318 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 874042' ####################################################################### # # 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_6 #TrackingRef '10447_web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1333099354.peptide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 N2 O5' _chemical_formula_sum 'C18 H24 N2 O5' _chemical_formula_weight 348.39 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.547(5) _cell_length_b 9.694(5) _cell_length_c 22.943(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1900.9(18) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 6175 _cell_measurement_theta_min 2.282 _cell_measurement_theta_max 27.210 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 1.37 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.47 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8873 _exptl_absorpt_correction_T_max 0.9591 _exptl_absorpt_process_details "Bruker's SADABS" _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18354 _diffrn_reflns_av_R_equivalents 0.0905 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3348 _reflns_number_gt 3213 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0887P)^2^+0.1311P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(11) _refine_ls_number_reflns 3348 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2730(2) 1.05720(19) 0.55220(10) 0.0871(6) Uani 1 1 d . . . O2 O -0.09827(17) 0.81376(12) 0.68062(6) 0.0509(3) Uani 1 1 d . . . O3 O -0.41725(17) 0.74361(16) 0.75465(8) 0.0673(4) Uani 1 1 d . . . O4 O -0.22595(19) 0.59544(12) 0.77747(7) 0.0588(4) Uani 1 1 d . . . O5 O 0.29010(17) 0.83240(14) 0.57711(7) 0.0591(4) Uani 1 1 d . . . N1 N 0.07981(19) 0.94782(15) 0.60263(6) 0.0477(3) Uani 1 1 d . . . H1 H 0.0574 0.8700 0.6186 0.057 Uiso 1 1 calc R . . N2 N -0.17261(17) 0.95039(15) 0.75386(6) 0.0418(3) Uani 1 1 d . . . C1 C 0.2201(2) 0.9560(2) 0.57462(8) 0.0509(4) Uani 1 1 d . . . C2 C -0.0320(2) 1.05293(18) 0.60824(7) 0.0453(4) Uani 1 1 d . . . C3 C -0.13526(19) 1.05009(17) 0.65622(7) 0.0412(4) Uani 1 1 d . . . C4 C -0.2513(2) 1.1515(2) 0.66053(9) 0.0521(4) Uani 1 1 d . . . H4 H -0.3202 1.1503 0.6919 0.063 Uiso 1 1 calc R . . C5 C -0.2647(3) 1.2535(2) 0.61863(10) 0.0659(5) Uani 1 1 d . . . H5 H -0.3427 1.3200 0.6217 0.079 Uiso 1 1 calc R . . C6 C -0.1620(3) 1.2561(2) 0.57221(10) 0.0706(6) Uani 1 1 d . . . H6 H -0.1701 1.3253 0.5443 0.085 Uiso 1 1 calc R . . C7 C -0.0478(3) 1.1570(2) 0.56698(9) 0.0617(5) Uani 1 1 d . . . H7 H 0.0200 1.1596 0.5353 0.074 Uiso 1 1 calc R . . C8 C -0.13202(18) 0.93103(17) 0.69754(7) 0.0398(4) Uani 1 1 d . . . C9 C -0.1719(2) 0.82957(18) 0.79208(8) 0.0443(4) Uani 1 1 d . . . H9 H -0.0664 0.7900 0.7936 0.053 Uiso 1 1 calc R . . C10 C -0.2147(3) 0.8910(2) 0.85163(8) 0.0567(5) Uani 1 1 d . . . H10A H -0.3271 0.8992 0.8563 0.068 Uiso 1 1 calc R . . H10B H -0.1725 0.8362 0.8833 0.068 Uiso 1 1 calc R . . C11 C -0.1371(3) 1.0316(2) 0.84852(9) 0.0601(5) Uani 1 1 d . . . H11A H -0.1791 1.0936 0.8778 0.072 Uiso 1 1 calc R . . H11B H -0.0247 1.0244 0.8537 0.072 Uiso 1 1 calc R . . C12 C -0.1777(2) 1.07995(19) 0.78763(8) 0.0520(5) Uani 1 1 d . . . H12A H -0.2810 1.1213 0.7864 0.062 Uiso 1 1 calc R . . H12B H -0.1015 1.1459 0.7733 0.062 Uiso 1 1 calc R . . C13 C -0.2877(2) 0.72070(17) 0.77184(8) 0.0446(4) Uani 1 1 d . . . C14 C -0.3256(4) 0.4816(2) 0.76038(14) 0.0842(8) Uani 1 1 d . . . H14A H -0.3528 0.4907 0.7200 0.126 Uiso 1 1 calc R . . H14B H -0.4190 0.4823 0.7836 0.126 Uiso 1 1 calc R . . H14C H -0.2710 0.3962 0.7662 0.126 Uiso 1 1 calc R . . C15 C 0.4500(2) 0.8098(2) 0.55382(10) 0.0582(5) Uani 1 1 d . . . C16 C 0.5633(3) 0.8972(4) 0.58704(17) 0.1109(12) Uani 1 1 d . . . H16A H 0.5468 0.8847 0.6281 0.166 Uiso 1 1 calc R . . H16B H 0.5476 0.9924 0.5771 0.166 Uiso 1 1 calc R . . H16C H 0.6683 0.8706 0.5772 0.166 Uiso 1 1 calc R . . C17 C 0.4528(4) 0.8400(4) 0.48940(12) 0.0958(9) Uani 1 1 d . . . H17A H 0.5494 0.8077 0.4730 0.144 Uiso 1 1 calc R . . H17B H 0.4438 0.9376 0.4833 0.144 Uiso 1 1 calc R . . H17C H 0.3668 0.7938 0.4708 0.144 Uiso 1 1 calc R . . C18 C 0.4766(4) 0.6599(3) 0.5631(2) 0.1121(12) Uani 1 1 d . . . H18A H 0.4859 0.6417 0.6041 0.168 Uiso 1 1 calc R . . H18B H 0.5710 0.6323 0.5437 0.168 Uiso 1 1 calc R . . H18C H 0.3899 0.6087 0.5476 0.168 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 0.0846(12) 0.0697(10) 0.1071(13) 0.0224(10) 0.0422(11) 0.0005(9) O2 0.0634(8) 0.0377(6) 0.0515(7) -0.0017(5) 0.0127(6) 0.0046(6) O3 0.0476(7) 0.0539(8) 0.1005(12) 0.0086(8) -0.0042(8) -0.0030(6) O4 0.0695(9) 0.0371(6) 0.0698(9) 0.0021(6) -0.0087(7) 0.0001(6) O5 0.0516(7) 0.0577(8) 0.0682(8) 0.0009(7) 0.0176(6) -0.0014(6) N1 0.0526(8) 0.0454(8) 0.0452(7) 0.0019(6) 0.0090(6) -0.0018(7) N2 0.0461(7) 0.0348(7) 0.0445(7) -0.0033(6) 0.0068(6) -0.0018(6) C1 0.0574(10) 0.0518(10) 0.0435(9) -0.0032(8) 0.0079(8) -0.0065(9) C2 0.0504(9) 0.0447(9) 0.0409(8) -0.0007(7) -0.0029(7) -0.0050(7) C3 0.0428(9) 0.0363(8) 0.0445(8) -0.0017(6) -0.0024(7) -0.0039(7) C4 0.0494(10) 0.0474(10) 0.0595(10) -0.0020(8) -0.0061(8) 0.0042(8) C5 0.0703(13) 0.0526(11) 0.0749(13) 0.0071(10) -0.0088(11) 0.0134(10) C6 0.0872(16) 0.0577(13) 0.0669(13) 0.0179(10) -0.0144(12) 0.0065(11) C7 0.0761(14) 0.0622(12) 0.0466(10) 0.0119(9) 0.0007(9) -0.0029(11) C8 0.0345(8) 0.0384(8) 0.0465(8) -0.0022(7) 0.0035(6) -0.0010(6) C9 0.0433(8) 0.0428(9) 0.0470(8) 0.0016(7) 0.0039(7) 0.0029(7) C10 0.0696(12) 0.0565(11) 0.0441(9) 0.0004(8) 0.0050(9) 0.0053(10) C11 0.0679(13) 0.0623(12) 0.0502(10) -0.0151(9) -0.0009(9) -0.0006(10) C12 0.0592(11) 0.0416(9) 0.0550(10) -0.0096(8) 0.0070(8) -0.0069(8) C13 0.0467(9) 0.0390(8) 0.0482(8) 0.0058(7) 0.0054(7) -0.0014(7) C14 0.111(2) 0.0417(12) 0.0997(18) -0.0050(11) -0.0123(16) -0.0124(12) C15 0.0447(10) 0.0703(13) 0.0596(11) -0.0080(10) 0.0107(9) -0.0039(9) C16 0.0597(15) 0.151(3) 0.122(3) -0.052(2) -0.0058(16) -0.0130(17) C17 0.0890(19) 0.136(3) 0.0626(14) -0.0091(16) 0.0237(13) 0.0252(19) C18 0.0760(18) 0.099(2) 0.162(3) 0.030(2) 0.048(2) 0.0244(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.197(2) . ? O2 C8 1.235(2) . ? O3 C13 1.196(3) . ? O4 C13 1.330(2) . ? O4 C14 1.448(3) . ? O5 C1 1.340(3) . ? O5 C15 1.484(2) . ? N1 C1 1.362(3) . ? N1 C2 1.403(2) . ? N1 H1 0.8600 . ? N2 C8 1.351(2) . ? N2 C9 1.463(2) . ? N2 C12 1.476(2) . ? C2 C7 1.390(3) . ? C2 C3 1.411(3) . ? C3 C4 1.400(3) . ? C3 C8 1.494(2) . ? C4 C5 1.384(3) . ? C4 H4 0.9300 . ? C5 C6 1.380(4) . ? C5 H5 0.9300 . ? C6 C7 1.375(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 C13 1.519(3) . ? C9 C10 1.535(3) . ? C9 H9 0.9800 . ? C10 C11 1.518(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.514(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C18 1.486(4) . ? C15 C16 1.496(4) . ? C15 C17 1.507(4) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 C13 O4 C14 115.87(19) . . ? C1 O5 C15 121.89(15) . . ? C1 N1 C2 126.91(15) . . ? C1 N1 H1 116.5 . . ? C2 N1 H1 116.5 . . ? C8 N2 C9 117.45(14) . . ? C8 N2 C12 128.88(15) . . ? C9 N2 C12 111.51(14) . . ? O1 C1 O5 125.61(18) . . ? O1 C1 N1 125.65(18) . . ? O5 C1 N1 108.73(15) . . ? C7 C2 N1 122.06(17) . . ? C7 C2 C3 118.99(18) . . ? N1 C2 C3 118.91(16) . . ? C4 C3 C2 118.98(17) . . ? C4 C3 C8 120.72(16) . . ? C2 C3 C8 119.90(15) . . ? C5 C4 C3 120.8(2) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 119.7(2) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C7 C6 C5 120.4(2) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C2 121.1(2) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? O2 C8 N2 119.23(15) . . ? O2 C8 C3 121.06(15) . . ? N2 C8 C3 119.66(15) . . ? N2 C9 C13 111.73(14) . . ? N2 C9 C10 102.81(14) . . ? C13 C9 C10 112.75(16) . . ? N2 C9 H9 109.8 . . ? C13 C9 H9 109.8 . . ? C10 C9 H9 109.8 . . ? C11 C10 C9 101.69(15) . . ? C11 C10 H10A 111.4 . . ? C9 C10 H10A 111.4 . . ? C11 C10 H10B 111.4 . . ? C9 C10 H10B 111.4 . . ? H10A C10 H10B 109.3 . . ? C12 C11 C10 102.77(16) . . ? C12 C11 H11A 111.2 . . ? C10 C11 H11A 111.2 . . ? C12 C11 H11B 111.2 . . ? C10 C11 H11B 111.2 . . ? H11A C11 H11B 109.1 . . ? N2 C12 C11 102.38(16) . . ? N2 C12 H12A 111.3 . . ? C11 C12 H12A 111.3 . . ? N2 C12 H12B 111.3 . . ? C11 C12 H12B 111.3 . . ? H12A C12 H12B 109.2 . . ? O3 C13 O4 124.65(17) . . ? O3 C13 C9 125.08(16) . . ? O4 C13 C9 110.25(16) . . ? O4 C14 H14A 109.5 . . ? O4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O5 C15 C18 103.50(19) . . ? O5 C15 C16 109.21(19) . . ? C18 C15 C16 112.4(3) . . ? O5 C15 C17 109.8(2) . . ? C18 C15 C17 109.2(3) . . ? C16 C15 C17 112.3(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 O5 C1 O1 3.1(3) . . . . ? C15 O5 C1 N1 -175.95(16) . . . . ? C2 N1 C1 O1 3.3(3) . . . . ? C2 N1 C1 O5 -177.68(16) . . . . ? C1 N1 C2 C7 28.3(3) . . . . ? C1 N1 C2 C3 -153.99(17) . . . . ? C7 C2 C3 C4 0.5(3) . . . . ? N1 C2 C3 C4 -177.24(15) . . . . ? C7 C2 C3 C8 173.32(16) . . . . ? N1 C2 C3 C8 -4.5(2) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C8 C3 C4 C5 -172.96(18) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C4 C5 C6 C7 0.8(4) . . . . ? C5 C6 C7 C2 -0.5(4) . . . . ? N1 C2 C7 C6 177.5(2) . . . . ? C3 C2 C7 C6 -0.2(3) . . . . ? C9 N2 C8 O2 0.8(2) . . . . ? C12 N2 C8 O2 162.55(18) . . . . ? C9 N2 C8 C3 178.23(14) . . . . ? C12 N2 C8 C3 -20.1(3) . . . . ? C4 C3 C8 O2 140.74(17) . . . . ? C2 C3 C8 O2 -31.9(2) . . . . ? C4 C3 C8 N2 -36.6(2) . . . . ? C2 C3 C8 N2 150.75(16) . . . . ? C8 N2 C9 C13 -61.59(19) . . . . ? C12 N2 C9 C13 133.64(16) . . . . ? C8 N2 C9 C10 177.25(16) . . . . ? C12 N2 C9 C10 12.47(19) . . . . ? N2 C9 C10 C11 -34.13(19) . . . . ? C13 C9 C10 C11 -154.60(16) . . . . ? C9 C10 C11 C12 43.6(2) . . . . ? C8 N2 C12 C11 -148.20(19) . . . . ? C9 N2 C12 C11 14.38(19) . . . . ? C10 C11 C12 N2 -35.67(19) . . . . ? C14 O4 C13 O3 0.9(3) . . . . ? C14 O4 C13 C9 179.16(19) . . . . ? N2 C9 C13 O3 -42.3(2) . . . . ? C10 C9 C13 O3 72.9(2) . . . . ? N2 C9 C13 O4 139.48(15) . . . . ? C10 C9 C13 O4 -105.32(18) . . . . ? C1 O5 C15 C18 -177.5(2) . . . . ? C1 O5 C15 C16 62.6(3) . . . . ? C1 O5 C15 C17 -61.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.160 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 874043' ####################################################################### # # 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_7 #TrackingRef '10447_web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1333099354.peptide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Peptide _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 N2 O5' _chemical_formula_sum 'C24 H28 N2 O5' _chemical_formula_weight 424.48 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.6231(7) _cell_length_b 10.9569(7) _cell_length_c 19.5280(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2273.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3486 _cell_measurement_theta_min 2.183 _cell_measurement_theta_max 21.684 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9632 _exptl_absorpt_correction_T_max 0.9882 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11578 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4004 _reflns_number_gt 3349 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.0449P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(10) _refine_ls_number_reflns 4004 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 1.00708(12) 0.47531(12) 0.18830(6) 0.0530(3) Uani 1 1 d . . . O2 O 0.93968(17) 0.30014(14) 0.13877(8) 0.0746(5) Uani 1 1 d . . . O3 O 0.75680(15) 0.71682(12) 0.09675(6) 0.0581(4) Uani 1 1 d . . . O4 O 0.54896(14) 0.89549(14) 0.01084(8) 0.0669(4) Uani 1 1 d . . . O5 O 0.65649(14) 1.03310(12) 0.07170(7) 0.0581(4) Uani 1 1 d . . . N1 N 0.87217(14) 0.48677(14) 0.10408(7) 0.0494(4) Uani 1 1 d . . . H1 H 0.8818 0.5632 0.1128 0.059 Uiso 1 1 calc R . . N2 N 0.76952(14) 0.76876(13) -0.01387(7) 0.0453(4) Uani 1 1 d . . . C1 C 0.94004(18) 0.40947(18) 0.14321(9) 0.0465(4) Uani 1 1 d . . . C2 C 0.78796(17) 0.45853(16) 0.05108(9) 0.0436(4) Uani 1 1 d . . . C3 C 0.7576(2) 0.33974(17) 0.03256(10) 0.0545(5) Uani 1 1 d . . . H3 H 0.7965 0.2744 0.0543 0.065 Uiso 1 1 calc R . . C4 C 0.6699(2) 0.3187(2) -0.01807(11) 0.0650(6) Uani 1 1 d . . . H4 H 0.6505 0.2387 -0.0301 0.078 Uiso 1 1 calc R . . C5 C 0.6106(2) 0.4127(2) -0.05108(11) 0.0642(6) Uani 1 1 d . . . H5 H 0.5501 0.3972 -0.0844 0.077 Uiso 1 1 calc R . . C6 C 0.6424(2) 0.5310(2) -0.03397(9) 0.0550(5) Uani 1 1 d . . . H6 H 0.6032 0.5954 -0.0565 0.066 Uiso 1 1 calc R . . C7 C 0.73137(17) 0.55586(16) 0.01594(9) 0.0421(4) Uani 1 1 d . . . C8 C 0.75561(17) 0.68560(16) 0.03577(9) 0.0442(4) Uani 1 1 d . . . C9 C 0.8005(2) 0.7503(2) -0.08638(9) 0.0579(5) Uani 1 1 d . . . H9A H 0.7250 0.7469 -0.1143 0.070 Uiso 1 1 calc R . . H9B H 0.8485 0.6760 -0.0930 0.070 Uiso 1 1 calc R . . C10 C 0.8781(2) 0.8616(2) -0.10290(12) 0.0699(6) Uani 1 1 d . . . H10A H 0.8760 0.8795 -0.1515 0.084 Uiso 1 1 calc R . . H10B H 0.9649 0.8510 -0.0886 0.084 Uiso 1 1 calc R . . C11 C 0.8138(2) 0.9611(2) -0.06182(11) 0.0675(6) Uani 1 1 d . . . H11A H 0.7412 0.9929 -0.0861 0.081 Uiso 1 1 calc R . . H11B H 0.8714 1.0278 -0.0524 0.081 Uiso 1 1 calc R . . C12 C 0.77417(18) 0.89699(16) 0.00454(9) 0.0481(5) Uani 1 1 d . . . H12 H 0.8373 0.9105 0.0404 0.058 Uiso 1 1 calc R . . C13 C 0.64662(19) 0.93827(16) 0.02875(10) 0.0474(4) Uani 1 1 d . . . C14 C 0.5402(2) 1.0862(2) 0.09546(12) 0.0720(7) Uani 1 1 d . . . H14A H 0.4791 1.0841 0.0585 0.086 Uiso 1 1 calc R . . H14B H 0.5549 1.1711 0.1071 0.086 Uiso 1 1 calc R . . C15 C 0.48586(19) 1.02197(19) 0.15688(10) 0.0535(5) Uani 1 1 d . . . C16 C 0.3810(2) 1.0737(2) 0.18741(14) 0.0773(7) Uani 1 1 d . . . H16 H 0.3465 1.1446 0.1692 0.093 Uiso 1 1 calc R . . C17 C 0.3279(3) 1.0220(3) 0.24367(17) 0.1037(10) Uani 1 1 d . . . H17 H 0.2588 1.0589 0.2643 0.124 Uiso 1 1 calc R . . C18 C 0.3752(3) 0.9163(3) 0.27012(16) 0.0965(9) Uani 1 1 d . . . H18 H 0.3388 0.8815 0.3088 0.116 Uiso 1 1 calc R . . C19 C 0.4766(2) 0.8614(3) 0.23953(13) 0.0817(8) Uani 1 1 d . . . H19 H 0.5078 0.7883 0.2567 0.098 Uiso 1 1 calc R . . C20 C 0.5323(2) 0.9153(2) 0.18303(11) 0.0654(6) Uani 1 1 d . . . H20 H 0.6019 0.8787 0.1627 0.079 Uiso 1 1 calc R . . C21 C 1.07500(19) 0.41567(18) 0.24509(9) 0.0520(5) Uani 1 1 d . . . C22 C 1.1339(3) 0.5235(2) 0.28127(12) 0.0781(7) Uani 1 1 d . . . H22A H 1.1911 0.5641 0.2507 0.117 Uiso 1 1 calc R . . H22B H 1.1789 0.4956 0.3209 0.117 Uiso 1 1 calc R . . H22C H 1.0691 0.5794 0.2951 0.117 Uiso 1 1 calc R . . C23 C 0.9825(3) 0.3517(3) 0.29117(12) 0.0774(7) Uani 1 1 d . . . H23A H 0.9205 0.4091 0.3068 0.116 Uiso 1 1 calc R . . H23B H 1.0262 0.3180 0.3298 0.116 Uiso 1 1 calc R . . H23C H 0.9417 0.2873 0.2663 0.116 Uiso 1 1 calc R . . C24 C 1.1742(2) 0.3300(2) 0.21839(12) 0.0734(7) Uani 1 1 d . . . H24A H 1.1345 0.2616 0.1965 0.110 Uiso 1 1 calc R . . H24B H 1.2251 0.3016 0.2558 0.110 Uiso 1 1 calc R . . H24C H 1.2263 0.3720 0.1859 0.110 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 0.0619(8) 0.0478(8) 0.0494(7) 0.0016(6) -0.0158(7) 0.0093(6) O2 0.1040(13) 0.0454(9) 0.0745(10) -0.0028(7) -0.0331(9) 0.0186(8) O3 0.0842(10) 0.0507(8) 0.0393(7) -0.0004(6) -0.0068(7) 0.0080(7) O4 0.0508(8) 0.0731(10) 0.0768(10) -0.0096(8) -0.0122(8) 0.0077(8) O5 0.0626(8) 0.0464(8) 0.0652(8) -0.0074(7) 0.0070(7) 0.0014(7) N1 0.0596(9) 0.0386(8) 0.0499(9) 0.0052(7) -0.0149(8) 0.0000(8) N2 0.0527(9) 0.0425(8) 0.0407(7) 0.0013(7) 0.0008(7) 0.0080(7) C1 0.0560(11) 0.0440(12) 0.0395(10) 0.0036(9) 0.0024(9) 0.0085(9) C2 0.0456(10) 0.0467(11) 0.0387(9) 0.0020(8) 0.0021(8) 0.0023(8) C3 0.0691(13) 0.0426(11) 0.0519(11) 0.0035(9) -0.0030(10) 0.0004(10) C4 0.0855(15) 0.0502(12) 0.0594(13) -0.0042(11) -0.0073(13) -0.0137(11) C5 0.0736(14) 0.0661(15) 0.0528(12) -0.0029(11) -0.0167(11) -0.0128(12) C6 0.0590(12) 0.0578(12) 0.0481(11) 0.0039(9) -0.0100(10) 0.0033(10) C7 0.0432(9) 0.0462(10) 0.0370(8) 0.0016(8) 0.0003(8) 0.0034(8) C8 0.0456(10) 0.0447(10) 0.0423(10) 0.0011(8) -0.0066(8) 0.0090(8) C9 0.0686(13) 0.0609(13) 0.0442(10) 0.0016(10) 0.0043(10) 0.0062(11) C10 0.0744(15) 0.0729(15) 0.0623(14) 0.0085(11) 0.0168(12) 0.0009(13) C11 0.0757(15) 0.0539(13) 0.0730(14) 0.0117(12) 0.0117(12) -0.0019(11) C12 0.0481(10) 0.0443(10) 0.0520(11) 0.0009(8) -0.0060(9) 0.0042(8) C13 0.0534(11) 0.0393(10) 0.0496(11) 0.0028(8) -0.0060(10) 0.0039(9) C14 0.0817(16) 0.0553(13) 0.0790(15) -0.0046(12) 0.0127(14) 0.0233(12) C15 0.0500(11) 0.0472(11) 0.0631(12) -0.0134(10) -0.0018(10) -0.0008(9) C16 0.0669(15) 0.0554(14) 0.110(2) -0.0029(13) 0.0191(15) 0.0092(12) C17 0.0812(18) 0.087(2) 0.143(3) 0.005(2) 0.056(2) 0.0112(17) C18 0.0795(18) 0.107(2) 0.103(2) 0.0193(17) 0.0364(17) 0.0084(17) C19 0.0691(16) 0.094(2) 0.0818(17) 0.0199(15) 0.0029(14) 0.0109(15) C20 0.0549(12) 0.0790(16) 0.0624(13) 0.0001(12) -0.0009(11) 0.0158(11) C21 0.0622(12) 0.0524(12) 0.0415(10) 0.0016(9) -0.0079(9) 0.0174(10) C22 0.0922(18) 0.0676(15) 0.0744(15) -0.0087(12) -0.0315(14) 0.0129(14) C23 0.0894(18) 0.0879(18) 0.0548(13) 0.0102(13) 0.0055(13) 0.0073(15) C24 0.0703(14) 0.0831(16) 0.0669(13) -0.0060(12) -0.0101(12) 0.0293(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.343(2) . ? O1 C21 1.476(2) . ? O2 C1 1.201(2) . ? O3 C8 1.239(2) . ? O4 C13 1.191(2) . ? O5 C13 1.340(2) . ? O5 C14 1.443(3) . ? N1 C1 1.349(2) . ? N1 C2 1.403(2) . ? N1 H1 0.8600 . ? N2 C8 1.339(2) . ? N2 C12 1.451(2) . ? N2 C9 1.468(2) . ? C2 C3 1.389(3) . ? C2 C7 1.403(2) . ? C3 C4 1.378(3) . ? C3 H3 0.9300 . ? C4 C5 1.368(3) . ? C4 H4 0.9300 . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? C6 C7 1.385(3) . ? C6 H6 0.9300 . ? C7 C8 1.496(3) . ? C9 C10 1.507(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.517(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.533(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.505(3) . ? C12 H12 0.9800 . ? C14 C15 1.506(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C20 1.367(3) . ? C15 C16 1.385(3) . ? C16 C17 1.359(4) . ? C16 H16 0.9300 . ? C17 C18 1.364(4) . ? C17 H17 0.9300 . ? C18 C19 1.370(4) . ? C18 H18 0.9300 . ? C19 C20 1.384(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C24 1.505(3) . ? C21 C23 1.506(3) . ? C21 C22 1.513(3) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 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 O1 C21 120.95(15) . . ? C13 O5 C14 116.58(17) . . ? C1 N1 C2 128.32(16) . . ? C1 N1 H1 115.8 . . ? C2 N1 H1 115.8 . . ? C8 N2 C12 118.91(14) . . ? C8 N2 C9 129.02(15) . . ? C12 N2 C9 111.40(15) . . ? O2 C1 O1 125.80(18) . . ? O2 C1 N1 125.69(19) . . ? O1 C1 N1 108.51(16) . . ? C3 C2 N1 123.17(16) . . ? C3 C2 C7 119.03(16) . . ? N1 C2 C7 117.80(16) . . ? C4 C3 C2 120.06(19) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 121.52(19) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C4 C5 C6 118.71(19) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C5 C6 C7 121.47(19) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C6 C7 C2 119.14(17) . . ? C6 C7 C8 119.13(16) . . ? C2 C7 C8 121.46(15) . . ? O3 C8 N2 120.46(16) . . ? O3 C8 C7 120.86(16) . . ? N2 C8 C7 118.58(15) . . ? N2 C9 C10 102.57(16) . . ? N2 C9 H9A 111.3 . . ? C10 C9 H9A 111.3 . . ? N2 C9 H9B 111.3 . . ? C10 C9 H9B 111.3 . . ? H9A C9 H9B 109.2 . . ? C9 C10 C11 102.85(17) . . ? C9 C10 H10A 111.2 . . ? C11 C10 H10A 111.2 . . ? C9 C10 H10B 111.2 . . ? C11 C10 H10B 111.2 . . ? H10A C10 H10B 109.1 . . ? C10 C11 C12 103.94(17) . . ? C10 C11 H11A 111.0 . . ? C12 C11 H11A 111.0 . . ? C10 C11 H11B 111.0 . . ? C12 C11 H11B 111.0 . . ? H11A C11 H11B 109.0 . . ? N2 C12 C13 109.76(16) . . ? N2 C12 C11 104.12(15) . . ? C13 C12 C11 112.04(16) . . ? N2 C12 H12 110.3 . . ? C13 C12 H12 110.3 . . ? C11 C12 H12 110.3 . . ? O4 C13 O5 123.87(19) . . ? O4 C13 C12 125.03(17) . . ? O5 C13 C12 111.06(17) . . ? O5 C14 C15 113.30(18) . . ? O5 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? O5 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C20 C15 C16 118.6(2) . . ? C20 C15 C14 123.98(19) . . ? C16 C15 C14 117.4(2) . . ? C17 C16 C15 120.7(2) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 120.5(3) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C19 119.8(3) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C20 119.8(3) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C15 C20 C19 120.5(2) . . ? C15 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? O1 C21 C24 111.00(16) . . ? O1 C21 C23 109.64(17) . . ? C24 C21 C23 112.0(2) . . ? O1 C21 C22 101.96(16) . . ? C24 C21 C22 111.08(19) . . ? C23 C21 C22 110.78(19) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 O1 C1 O2 -9.2(3) . . . . ? C21 O1 C1 N1 170.22(15) . . . . ? C2 N1 C1 O2 0.2(3) . . . . ? C2 N1 C1 O1 -179.22(16) . . . . ? C1 N1 C2 C3 2.9(3) . . . . ? C1 N1 C2 C7 -177.80(17) . . . . ? N1 C2 C3 C4 177.17(18) . . . . ? C7 C2 C3 C4 -2.2(3) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 1.6(4) . . . . ? C4 C5 C6 C7 -0.6(3) . . . . ? C5 C6 C7 C2 -1.7(3) . . . . ? C5 C6 C7 C8 -175.8(2) . . . . ? C3 C2 C7 C6 3.1(3) . . . . ? N1 C2 C7 C6 -176.33(17) . . . . ? C3 C2 C7 C8 177.03(17) . . . . ? N1 C2 C7 C8 -2.3(3) . . . . ? C12 N2 C8 O3 -5.7(3) . . . . ? C9 N2 C8 O3 164.04(19) . . . . ? C12 N2 C8 C7 170.87(16) . . . . ? C9 N2 C8 C7 -19.4(3) . . . . ? C6 C7 C8 O3 130.61(19) . . . . ? C2 C7 C8 O3 -43.4(3) . . . . ? C6 C7 C8 N2 -45.9(3) . . . . ? C2 C7 C8 N2 140.07(17) . . . . ? C8 N2 C9 C10 -146.1(2) . . . . ? C12 N2 C9 C10 24.3(2) . . . . ? N2 C9 C10 C11 -37.1(2) . . . . ? C9 C10 C11 C12 37.0(2) . . . . ? C8 N2 C12 C13 -69.7(2) . . . . ? C9 N2 C12 C13 118.85(18) . . . . ? C8 N2 C12 C11 170.20(17) . . . . ? C9 N2 C12 C11 -1.2(2) . . . . ? C10 C11 C12 N2 -22.3(2) . . . . ? C10 C11 C12 C13 -140.82(18) . . . . ? C14 O5 C13 O4 -1.5(3) . . . . ? C14 O5 C13 C12 176.36(16) . . . . ? N2 C12 C13 O4 -28.5(3) . . . . ? C11 C12 C13 O4 86.7(2) . . . . ? N2 C12 C13 O5 153.70(14) . . . . ? C11 C12 C13 O5 -91.1(2) . . . . ? C13 O5 C14 C15 85.1(2) . . . . ? O5 C14 C15 C20 -7.6(3) . . . . ? O5 C14 C15 C16 173.79(19) . . . . ? C20 C15 C16 C17 2.3(4) . . . . ? C14 C15 C16 C17 -179.0(3) . . . . ? C15 C16 C17 C18 -1.7(5) . . . . ? C16 C17 C18 C19 -0.3(5) . . . . ? C17 C18 C19 C20 1.6(5) . . . . ? C16 C15 C20 C19 -1.0(3) . . . . ? C14 C15 C20 C19 -179.6(2) . . . . ? C18 C19 C20 C15 -0.9(4) . . . . ? C1 O1 C21 C24 62.0(2) . . . . ? C1 O1 C21 C23 -62.2(2) . . . . ? C1 O1 C21 C22 -179.58(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.151 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 679454' ####################################################################### # # 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_8 #TrackingRef '10447_web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1333099354.peptide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 N2 O5' _chemical_formula_sum 'C16 H20 N2 O5' _chemical_formula_weight 320.34 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 8.111(2) _cell_length_b 9.756(2) _cell_length_c 20.126(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1592.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4943 _cell_measurement_theta_min 2.318 _cell_measurement_theta_max 28.349 _exptl_crystal_description 'thick plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9517 _exptl_absorpt_correction_T_max 0.9778 _exptl_absorpt_process_details "Beuker's SADABS" _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'BRUKER SMART APEX' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8457 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -8 _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 26 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.41 _reflns_number_total 3901 _reflns_number_gt 3560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.2629P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(8) _refine_ls_number_reflns 3901 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0823 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.31817(15) 1.02741(11) 0.55090(7) 0.0470(3) Uani 1 1 d . . . O2 O 0.90451(13) 0.77090(9) 0.67600(5) 0.0287(2) Uani 1 1 d . . . O3 O 0.57247(12) 0.69965(10) 0.75677(5) 0.0327(2) Uani 1 1 d . . . O4 O 0.77888(13) 0.55701(9) 0.78108(5) 0.0293(2) Uani 1 1 d . . . O5 O 1.33832(13) 0.80375(10) 0.57751(5) 0.0336(2) Uani 1 1 d . . . N1 N 1.10033(15) 0.90519(11) 0.59067(5) 0.0258(2) Uani 1 1 d . . . H1 H 1.0698 0.8217 0.6017 0.031 Uiso 1 1 calc R . . N2 N 0.82282(14) 0.90911(10) 0.75766(6) 0.0232(2) Uani 1 1 d . . . C1 C 1.25772(19) 0.92288(14) 0.57089(7) 0.0287(3) Uani 1 1 d . . . C2 C 0.98145(18) 1.00887(13) 0.59512(6) 0.0249(3) Uani 1 1 d . . . C3 C 0.86430(17) 1.00404(13) 0.64624(6) 0.0238(3) Uani 1 1 d . . . C4 C 0.74207(19) 1.10310(15) 0.64843(7) 0.0311(3) Uani 1 1 d . . . H4 H 0.6603 1.0990 0.6822 0.037 Uiso 1 1 calc R . . C5 C 0.7375(2) 1.20800(16) 0.60213(8) 0.0377(4) Uani 1 1 d . . . H5 H 0.6533 1.2756 0.6043 0.045 Uiso 1 1 calc R . . C6 C 0.8549(2) 1.21406(15) 0.55310(7) 0.0363(4) Uani 1 1 d . . . H6 H 0.8527 1.2868 0.5217 0.044 Uiso 1 1 calc R . . C7 C 0.9760(2) 1.11512(14) 0.54919(7) 0.0312(3) Uani 1 1 d . . . H7 H 1.0563 1.1197 0.5149 0.037 Uiso 1 1 calc R . . C8 C 0.86684(17) 0.88753(13) 0.69433(6) 0.0229(3) Uani 1 1 d . . . C9 C 0.82212(17) 0.79060(13) 0.80265(7) 0.0237(3) Uani 1 1 d . . . H9 H 0.9365 0.7539 0.8079 0.028 Uiso 1 1 calc R . . C10 C 0.7634(2) 0.85368(14) 0.86798(7) 0.0307(3) Uani 1 1 d . . . H10A H 0.6416 0.8596 0.8697 0.037 Uiso 1 1 calc R . . H10B H 0.8033 0.8005 0.9067 0.037 Uiso 1 1 calc R . . C11 C 0.8415(2) 0.99539(14) 0.86573(7) 0.0328(3) Uani 1 1 d . . . H11A H 0.7881 1.0584 0.8977 0.039 Uiso 1 1 calc R . . H11B H 0.9611 0.9910 0.8754 0.039 Uiso 1 1 calc R . . C12 C 0.81000(19) 1.03982(13) 0.79462(7) 0.0288(3) Uani 1 1 d . . . H12A H 0.6991 1.0809 0.7897 0.035 Uiso 1 1 calc R . . H12B H 0.8940 1.1065 0.7794 0.035 Uiso 1 1 calc R . . C13 C 0.70897(17) 0.67984(13) 0.77660(6) 0.0236(3) Uani 1 1 d . . . C14 C 0.6799(2) 0.44335(15) 0.75837(9) 0.0419(4) Uani 1 1 d . . . H14A H 0.6487 0.4581 0.7119 0.063 Uiso 1 1 calc R . . H14B H 0.5802 0.4365 0.7857 0.063 Uiso 1 1 calc R . . H14C H 0.7435 0.3583 0.7621 0.063 Uiso 1 1 calc R . . C15 C 1.5102(2) 0.80531(18) 0.55864(9) 0.0443(4) Uani 1 1 d . . . H15A H 1.5685 0.8815 0.5811 0.053 Uiso 1 1 calc R . . H15B H 1.5213 0.8172 0.5100 0.053 Uiso 1 1 calc R . . C16 C 1.5804(2) 0.67125(19) 0.57958(9) 0.0470(4) Uani 1 1 d . . . H16A H 1.5239 0.5970 0.5560 0.070 Uiso 1 1 calc R . . H16B H 1.5653 0.6596 0.6276 0.070 Uiso 1 1 calc R . . H16C H 1.6983 0.6688 0.5690 0.070 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 0.0424(7) 0.0344(6) 0.0642(8) 0.0144(6) 0.0146(6) -0.0056(5) O2 0.0335(6) 0.0202(4) 0.0322(5) 0.0008(4) 0.0083(4) 0.0003(4) O3 0.0242(5) 0.0283(5) 0.0455(6) 0.0047(4) -0.0020(4) -0.0020(4) O4 0.0350(6) 0.0176(4) 0.0354(5) 0.0009(4) -0.0058(4) -0.0005(4) O5 0.0292(6) 0.0283(5) 0.0432(6) -0.0010(4) 0.0086(5) 0.0001(4) N1 0.0306(6) 0.0193(5) 0.0273(5) 0.0011(4) 0.0058(5) -0.0018(5) N2 0.0249(6) 0.0163(5) 0.0285(5) 0.0021(4) 0.0021(4) -0.0012(4) C1 0.0329(8) 0.0268(7) 0.0263(6) 0.0000(5) 0.0040(6) -0.0025(6) C2 0.0298(7) 0.0215(6) 0.0235(6) -0.0008(5) -0.0034(5) -0.0026(6) C3 0.0239(7) 0.0212(6) 0.0262(6) 0.0018(5) -0.0032(5) -0.0019(5) C4 0.0290(8) 0.0291(7) 0.0352(7) 0.0024(6) -0.0010(6) 0.0032(6) C5 0.0396(9) 0.0313(7) 0.0421(8) 0.0051(6) -0.0075(7) 0.0110(7) C6 0.0482(10) 0.0294(7) 0.0312(7) 0.0092(6) -0.0094(7) 0.0022(7) C7 0.0395(9) 0.0288(7) 0.0253(7) 0.0050(6) -0.0008(6) -0.0017(7) C8 0.0189(6) 0.0215(6) 0.0284(6) 0.0013(5) 0.0022(5) -0.0025(5) C9 0.0236(7) 0.0197(6) 0.0279(6) 0.0024(5) 0.0009(5) -0.0003(5) C10 0.0375(9) 0.0276(7) 0.0271(7) 0.0017(5) 0.0031(6) 0.0021(6) C11 0.0377(9) 0.0278(7) 0.0330(7) -0.0059(6) -0.0011(6) -0.0008(6) C12 0.0344(8) 0.0185(6) 0.0336(7) -0.0020(5) 0.0011(6) -0.0013(6) C13 0.0262(7) 0.0216(6) 0.0231(6) 0.0045(5) 0.0031(5) -0.0016(5) C14 0.0539(11) 0.0210(6) 0.0507(9) -0.0020(6) -0.0140(8) -0.0052(7) C15 0.0312(9) 0.0486(9) 0.0532(10) -0.0060(8) 0.0102(7) -0.0002(8) C16 0.0368(9) 0.0638(12) 0.0403(9) -0.0066(8) 0.0008(7) 0.0125(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2009(17) . ? O2 C8 1.2346(16) . ? O3 C13 1.1926(17) . ? O4 C13 1.3288(15) . ? O4 C14 1.4432(17) . ? O5 C1 1.3402(17) . ? O5 C15 1.445(2) . ? N1 C1 1.3482(19) . ? N1 C2 1.4003(17) . ? N1 H1 0.8800 . ? N2 C8 1.3403(18) . ? N2 C9 1.4686(16) . ? N2 C12 1.4800(17) . ? C2 C7 1.3895(18) . ? C2 C3 1.401(2) . ? C3 C4 1.385(2) . ? C3 C8 1.4930(17) . ? C4 C5 1.385(2) . ? C4 H4 0.9500 . ? C5 C6 1.372(2) . ? C5 H5 0.9500 . ? C6 C7 1.380(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C9 C13 1.5115(19) . ? C9 C10 1.5279(19) . ? C9 H9 1.0000 . ? C10 C11 1.521(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.517(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.488(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 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 C13 O4 C14 115.73(11) . . ? C1 O5 C15 115.81(12) . . ? C1 N1 C2 125.33(12) . . ? C1 N1 H1 117.3 . . ? C2 N1 H1 117.3 . . ? C8 N2 C9 117.63(11) . . ? C8 N2 C12 129.20(11) . . ? C9 N2 C12 111.60(11) . . ? O1 C1 O5 124.79(14) . . ? O1 C1 N1 126.46(14) . . ? O5 C1 N1 108.76(12) . . ? C7 C2 N1 121.20(13) . . ? C7 C2 C3 119.48(13) . . ? N1 C2 C3 119.31(11) . . ? C4 C3 C2 119.02(12) . . ? C4 C3 C8 121.36(12) . . ? C2 C3 C8 119.49(12) . . ? C5 C4 C3 120.90(15) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 119.81(15) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 120.33(13) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C2 120.43(14) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? O2 C8 N2 119.66(11) . . ? O2 C8 C3 120.76(12) . . ? N2 C8 C3 119.55(11) . . ? N2 C9 C13 110.57(11) . . ? N2 C9 C10 102.40(10) . . ? C13 C9 C10 113.41(12) . . ? N2 C9 H9 110.1 . . ? C13 C9 H9 110.1 . . ? C10 C9 H9 110.1 . . ? C11 C10 C9 102.16(11) . . ? C11 C10 H10A 111.3 . . ? C9 C10 H10A 111.3 . . ? C11 C10 H10B 111.3 . . ? C9 C10 H10B 111.3 . . ? H10A C10 H10B 109.2 . . ? C12 C11 C10 102.56(11) . . ? C12 C11 H11A 111.3 . . ? C10 C11 H11A 111.3 . . ? C12 C11 H11B 111.3 . . ? C10 C11 H11B 111.3 . . ? H11A C11 H11B 109.2 . . ? N2 C12 C11 102.49(11) . . ? N2 C12 H12A 111.3 . . ? C11 C12 H12A 111.3 . . ? N2 C12 H12B 111.3 . . ? C11 C12 H12B 111.3 . . ? H12A C12 H12B 109.2 . . ? O3 C13 O4 124.39(13) . . ? O3 C13 C9 124.32(12) . . ? O4 C13 C9 111.24(12) . . ? O4 C14 H14A 109.5 . . ? O4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O5 C15 C16 106.60(14) . . ? O5 C15 H15A 110.4 . . ? C16 C15 H15A 110.4 . . ? O5 C15 H15B 110.4 . . ? C16 C15 H15B 110.4 . . ? H15A C15 H15B 108.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 O5 C1 O1 -0.1(2) . . . . ? C15 O5 C1 N1 -179.66(13) . . . . ? C2 N1 C1 O1 -4.1(2) . . . . ? C2 N1 C1 O5 175.47(12) . . . . ? C1 N1 C2 C7 36.41(19) . . . . ? C1 N1 C2 C3 -144.62(14) . . . . ? C7 C2 C3 C4 2.2(2) . . . . ? N1 C2 C3 C4 -176.81(12) . . . . ? C7 C2 C3 C8 178.09(12) . . . . ? N1 C2 C3 C8 -0.90(19) . . . . ? C2 C3 C4 C5 -1.8(2) . . . . ? C8 C3 C4 C5 -177.67(14) . . . . ? C3 C4 C5 C6 0.3(2) . . . . ? C4 C5 C6 C7 0.9(2) . . . . ? C5 C6 C7 C2 -0.5(2) . . . . ? N1 C2 C7 C6 177.95(13) . . . . ? C3 C2 C7 C6 -1.0(2) . . . . ? C9 N2 C8 O2 0.1(2) . . . . ? C12 N2 C8 O2 164.51(14) . . . . ? C9 N2 C8 C3 178.09(12) . . . . ? C12 N2 C8 C3 -17.5(2) . . . . ? C4 C3 C8 O2 140.17(14) . . . . ? C2 C3 C8 O2 -35.6(2) . . . . ? C4 C3 C8 N2 -37.8(2) . . . . ? C2 C3 C8 N2 146.41(13) . . . . ? C8 N2 C9 C13 -57.69(16) . . . . ? C12 N2 C9 C13 135.26(12) . . . . ? C8 N2 C9 C10 -178.82(12) . . . . ? C12 N2 C9 C10 14.13(15) . . . . ? N2 C9 C10 C11 -35.16(14) . . . . ? C13 C9 C10 C11 -154.31(12) . . . . ? C9 C10 C11 C12 43.68(15) . . . . ? C8 N2 C12 C11 -152.43(14) . . . . ? C9 N2 C12 C11 12.72(15) . . . . ? C10 C11 C12 N2 -34.46(15) . . . . ? C14 O4 C13 O3 1.5(2) . . . . ? C14 O4 C13 C9 179.11(12) . . . . ? N2 C9 C13 O3 -46.89(18) . . . . ? C10 C9 C13 O3 67.46(17) . . . . ? N2 C9 C13 O4 135.54(11) . . . . ? C10 C9 C13 O4 -110.10(13) . . . . ? C1 O5 C15 C16 171.44(13) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.177 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 874044' ####################################################################### # # 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_9 #TrackingRef '10447_web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1333099354.peptide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H34 N2 O5' _chemical_formula_sum 'C25 H34 N2 O5' _chemical_formula_weight 442.54 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 7.4115(4) _cell_length_b 16.5480(9) _cell_length_c 19.3577(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2374.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8545 _cell_measurement_theta_min 2.437 _cell_measurement_theta_max 30.608 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.59 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9486 _exptl_absorpt_correction_T_max 0.9772 _exptl_absorpt_process_details "Bruker's SADABS" _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17494 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4176 _reflns_number_gt 3999 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+1.1915P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0049(10) _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 -0.2(11) _refine_ls_number_reflns 4176 _refine_ls_number_parameters 331 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1054 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8146(3) 0.99019(14) 0.86180(15) 0.0378(6) Uani 1 1 d . . . C2 C 0.5785(3) 0.94182(14) 0.94216(13) 0.0317(5) Uani 1 1 d . . . C3 C 0.4656(3) 0.87577(13) 0.95835(12) 0.0255(5) Uani 1 1 d . . . C4 C 0.3371(3) 0.88365(13) 1.01078(12) 0.0275(5) Uani 1 1 d . . . H4 H 0.2625 0.8389 1.0222 0.033 Uiso 1 1 calc R . . C5 C 0.3168(3) 0.95555(14) 1.04632(14) 0.0348(6) Uani 1 1 d . . . H5 H 0.2311 0.9600 1.0826 0.042 Uiso 1 1 calc R . . C6 C 0.4229(3) 1.02069(14) 1.02820(16) 0.0430(7) Uani 1 1 d . . . H6 H 0.4069 1.0707 1.0514 0.052 Uiso 1 1 calc R . . C7 C 0.5522(3) 1.01462(15) 0.97694(17) 0.0451(7) Uani 1 1 d . . . H7 H 0.6235 1.0604 0.9654 0.054 Uiso 1 1 calc R . . C8 C 0.4938(3) 0.79626(12) 0.92382(11) 0.0233(5) Uani 1 1 d . . . C9 C 0.3858(3) 0.66964(12) 0.87890(11) 0.0228(5) Uani 1 1 d . . . H9 H 0.4461 0.6351 0.9144 0.027 Uiso 1 1 calc R . . C10 C 0.1952(3) 0.63664(14) 0.86434(13) 0.0307(5) Uani 1 1 d . . . H10A H 0.1952 0.6008 0.8234 0.037 Uiso 1 1 calc R . . H10B H 0.1481 0.6063 0.9046 0.037 Uiso 1 1 calc R . . C11 C 0.0835(3) 0.71268(14) 0.85107(12) 0.0305(5) Uani 1 1 d . . . H11A H 0.1007 0.7325 0.8033 0.037 Uiso 1 1 calc R . . H11B H -0.0465 0.7024 0.8590 0.037 Uiso 1 1 calc R . . C12 C 0.1573(3) 0.77250(13) 0.90326(12) 0.0263(5) Uani 1 1 d . . . H12A H 0.1430 0.8288 0.8868 0.032 Uiso 1 1 calc R . . H12B H 0.0964 0.7667 0.9485 0.032 Uiso 1 1 calc R . . C13 C 0.4993(3) 0.67091(12) 0.81366(10) 0.0212(4) Uani 1 1 d . . . C14 C 0.5332(3) 0.73390(14) 0.70447(11) 0.0265(5) Uani 1 1 d . . . H14 H 0.5348 0.6789 0.6830 0.032 Uiso 1 1 calc R A 1 C15 C 0.7324(10) 0.7729(5) 0.7107(5) 0.051(2) Uani 0.60 1 d P B 1 H15A H 0.7585 0.7904 0.7586 0.061 Uiso 0.60 1 calc PR B 1 H15B H 0.8266 0.7345 0.6954 0.061 Uiso 0.60 1 calc PR B 1 C16 C 0.7171(11) 0.8457(6) 0.6613(6) 0.045(3) Uani 0.50 1 d P B 1 H16 H 0.8352 0.8647 0.6423 0.054 Uiso 0.50 1 calc PR B 1 C17 C 0.6117(14) 0.9113(6) 0.7021(6) 0.065(3) Uani 0.50 1 d P B 1 H17A H 0.6512 0.9150 0.7509 0.078 Uiso 0.50 1 calc PR B 1 H17B H 0.6193 0.9651 0.6800 0.078 Uiso 0.50 1 calc PR B 1 C15' C 0.7280(17) 0.7466(6) 0.6901(5) 0.025(2) Uani 0.40 1 d P B 2 H15C H 0.7837 0.6976 0.6699 0.030 Uiso 0.40 1 calc PR B 2 H15D H 0.7943 0.7618 0.7326 0.030 Uiso 0.40 1 calc PR B 2 C16' C 0.7243(12) 0.8165(5) 0.6379(4) 0.0292(17) Uani 0.50 1 d P B 2 H16' H 0.8369 0.8216 0.6098 0.035 Uiso 0.50 1 calc PR B 2 C17' C 0.6716(14) 0.8938(6) 0.6766(4) 0.047(3) Uani 0.50 1 d P B 2 H17C H 0.6875 0.9422 0.6471 0.056 Uiso 0.50 1 calc PR B 2 H17D H 0.7438 0.9004 0.7193 0.056 Uiso 0.50 1 calc PR B 2 C18 C 0.4444(5) 0.87761(16) 0.69576(17) 0.0574(9) Uani 1 1 d . . . H18A H 0.3668 0.9159 0.6701 0.069 Uiso 1 1 calc R B 1 H18B H 0.3924 0.8717 0.7426 0.069 Uiso 1 1 calc R B 1 C19 C 0.4342(3) 0.79604(13) 0.65994(12) 0.0250(5) Uani 1 1 d . B . C20 C 0.5708(4) 0.80638(17) 0.59945(15) 0.0486(8) Uani 1 1 d D . . C21 C 0.5179(4) 0.87191(19) 0.54692(16) 0.0543(8) Uani 1 1 d . B . H21A H 0.4029 0.8575 0.5252 0.082 Uiso 1 1 calc R . . H21B H 0.6116 0.8761 0.5114 0.082 Uiso 1 1 calc R . . H21C H 0.5054 0.9239 0.5707 0.082 Uiso 1 1 calc R . . C22 C 0.6684(12) 0.7398(6) 0.5629(5) 0.071(4) Uani 0.40 1 d PD B 1 H22A H 0.7698 0.7624 0.5368 0.106 Uiso 0.40 1 calc PR B 1 H22B H 0.5855 0.7125 0.5311 0.106 Uiso 0.40 1 calc PR B 1 H22C H 0.7139 0.7009 0.5969 0.106 Uiso 0.40 1 calc PR B 1 C22' C 0.5758(9) 0.7260(3) 0.5564(3) 0.0516(17) Uani 0.60 1 d PD B 2 H22D H 0.6469 0.7345 0.5143 0.077 Uiso 0.60 1 calc PR B 2 H22E H 0.4526 0.7103 0.5439 0.077 Uiso 0.60 1 calc PR B 2 H22F H 0.6312 0.6831 0.5840 0.077 Uiso 0.60 1 calc PR B 2 C23 C 0.2446(4) 0.7704(2) 0.64118(17) 0.0566(9) Uani 1 1 d . . . H23A H 0.1706 0.7677 0.6831 0.085 Uiso 1 1 calc R B . H23B H 0.2480 0.7170 0.6192 0.085 Uiso 1 1 calc R . . H23C H 0.1923 0.8097 0.6091 0.085 Uiso 1 1 calc R . . C24 C 1.0721(3) 1.00640(16) 0.78979(14) 0.0395(6) Uani 1 1 d . . . H24A H 1.0166 1.0596 0.7802 0.047 Uiso 1 1 calc R . . H24B H 1.1126 0.9829 0.7454 0.047 Uiso 1 1 calc R . . C25 C 1.2305(4) 1.01691(17) 0.83695(16) 0.0454(7) Uani 1 1 d . . . H25A H 1.2795 0.9638 0.8492 0.068 Uiso 1 1 calc R . . H25B H 1.1920 1.0450 0.8790 0.068 Uiso 1 1 calc R . . H25C H 1.3236 1.0488 0.8136 0.068 Uiso 1 1 calc R . . N1 N 0.7147(3) 0.93124(12) 0.89283(12) 0.0376(5) Uani 1 1 d . . . H1 H 0.7384 0.8812 0.8805 0.045 Uiso 1 1 calc R . . N2 N 0.3511(2) 0.74974(10) 0.90795(9) 0.0220(4) Uani 1 1 d . . . O1 O 0.7968(3) 1.06191(10) 0.86821(12) 0.0539(6) Uani 1 1 d . . . O2 O 0.64943(19) 0.77155(9) 0.91164(8) 0.0258(3) Uani 1 1 d . . . O3 O 0.6038(2) 0.61832(10) 0.79847(8) 0.0293(4) Uani 1 1 d . . . O4 O 0.45626(19) 0.73363(8) 0.77338(7) 0.0235(3) Uani 1 1 d . B . O5 O 0.9403(2) 0.95358(10) 0.82168(10) 0.0382(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 C1 0.0203(12) 0.0246(13) 0.0685(18) -0.0036(12) -0.0024(12) -0.0048(10) C2 0.0158(11) 0.0218(11) 0.0576(15) -0.0076(10) -0.0036(11) -0.0013(9) C3 0.0186(11) 0.0206(11) 0.0374(12) -0.0028(9) -0.0065(9) -0.0005(9) C4 0.0232(11) 0.0212(11) 0.0380(12) -0.0029(10) -0.0067(10) -0.0021(10) C5 0.0219(12) 0.0264(12) 0.0561(16) -0.0118(11) -0.0013(11) 0.0037(10) C6 0.0255(12) 0.0243(12) 0.0792(19) -0.0223(13) 0.0011(13) -0.0001(11) C7 0.0207(12) 0.0223(12) 0.092(2) -0.0175(13) 0.0020(13) -0.0056(10) C8 0.0196(11) 0.0182(11) 0.0319(11) -0.0013(8) -0.0022(9) -0.0028(8) C9 0.0236(11) 0.0150(9) 0.0298(11) -0.0002(8) -0.0015(9) -0.0045(8) C10 0.0250(12) 0.0264(12) 0.0408(13) -0.0103(10) 0.0033(10) -0.0082(10) C11 0.0178(11) 0.0334(13) 0.0403(12) -0.0070(10) 0.0008(10) -0.0053(10) C12 0.0175(10) 0.0234(11) 0.0381(12) -0.0007(10) -0.0014(9) -0.0024(9) C13 0.0171(10) 0.0167(10) 0.0299(11) -0.0025(8) -0.0068(9) -0.0025(9) C14 0.0221(11) 0.0264(11) 0.0312(11) 0.0062(9) 0.0057(9) 0.0083(9) C15 0.008(2) 0.074(6) 0.071(6) 0.022(4) -0.004(3) 0.010(4) C16 0.017(3) 0.038(6) 0.079(8) 0.004(4) -0.015(5) -0.017(4) C17 0.065(6) 0.036(4) 0.095(8) 0.004(6) -0.014(6) -0.015(4) C15' 0.024(4) 0.034(5) 0.017(4) 0.009(3) -0.011(3) -0.004(4) C16' 0.023(3) 0.033(4) 0.032(4) 0.004(3) 0.004(3) -0.007(3) C17' 0.077(8) 0.039(6) 0.023(3) -0.006(3) -0.001(3) -0.041(6) C18 0.090(3) 0.0207(13) 0.0620(18) 0.0036(13) -0.0065(18) 0.0069(15) C19 0.0164(10) 0.0196(11) 0.0388(12) 0.0070(9) -0.0001(9) 0.0025(9) C20 0.0323(14) 0.0536(17) 0.0598(17) 0.0345(14) 0.0184(13) 0.0194(13) C21 0.0325(15) 0.0594(18) 0.071(2) 0.0400(16) 0.0160(14) 0.0105(14) C22 0.032(5) 0.107(8) 0.072(6) 0.060(6) 0.025(5) 0.042(6) C22' 0.058(4) 0.054(3) 0.043(3) 0.025(2) 0.030(3) 0.046(3) C23 0.0345(15) 0.0650(19) 0.0704(19) 0.0456(17) -0.0233(14) -0.0184(14) C24 0.0275(13) 0.0362(14) 0.0549(16) 0.0102(12) 0.0004(12) -0.0105(11) C25 0.0300(14) 0.0433(16) 0.0628(17) 0.0097(14) -0.0027(13) -0.0201(12) N1 0.0215(10) 0.0186(9) 0.0727(15) -0.0116(10) 0.0064(10) -0.0052(8) N2 0.0194(9) 0.0161(8) 0.0305(9) -0.0038(7) -0.0014(7) -0.0002(7) O1 0.0433(11) 0.0204(9) 0.0980(16) 0.0019(10) 0.0112(12) -0.0044(8) O2 0.0184(8) 0.0201(7) 0.0390(9) -0.0044(7) -0.0020(6) 0.0002(6) O3 0.0258(8) 0.0273(8) 0.0349(8) 0.0029(7) 0.0002(7) 0.0098(7) O4 0.0223(8) 0.0189(7) 0.0293(7) -0.0006(6) -0.0010(6) 0.0032(6) O5 0.0209(8) 0.0291(9) 0.0646(11) -0.0028(8) 0.0036(8) -0.0109(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.201(3) . ? C1 O5 1.356(3) . ? C1 N1 1.364(3) . ? C2 C7 1.394(3) . ? C2 N1 1.400(3) . ? C2 C3 1.412(3) . ? C3 C4 1.398(3) . ? C3 C8 1.491(3) . ? C4 C5 1.383(3) . ? C4 H4 0.9500 . ? C5 C6 1.380(4) . ? C5 H5 0.9500 . ? C6 C7 1.383(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 O2 1.246(3) . ? C8 N2 1.344(3) . ? C9 N2 1.462(3) . ? C9 C13 1.518(3) . ? C9 C10 1.541(3) . ? C9 H9 1.0000 . ? C10 C11 1.528(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.516(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N2 1.488(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O3 1.201(3) . ? C13 O4 1.337(2) . ? C14 O4 1.451(3) . ? C14 C15' 1.485(13) . ? C14 C19 1.529(3) . ? C14 C15 1.615(8) . ? C14 H14 1.0000 . ? C15 C16 1.544(13) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.553(12) . ? C16 C20 1.742(9) . ? C16 H16 1.0000 . ? C17 C18 1.365(11) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C15' C16' 1.537(14) . ? C15' H15C 0.9900 . ? C15' H15D 0.9900 . ? C16' C20 1.370(9) . ? C16' C17' 1.534(10) . ? C16' H16' 1.0000 . ? C17' C18 1.745(10) . ? C17' H17C 0.9900 . ? C17' H17D 0.9900 . ? C18 C19 1.519(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C23 1.513(3) . ? C19 C20 1.557(3) . ? C20 C22 1.496(8) . ? C20 C21 1.537(3) . ? C20 C22' 1.570(6) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C22' H22D 0.9800 . ? C22' H22E 0.9800 . ? C22' H22F 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 O5 1.449(3) . ? C24 C25 1.497(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? N1 H1 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O5 125.2(2) . . ? O1 C1 N1 127.0(3) . . ? O5 C1 N1 107.8(2) . . ? C7 C2 N1 122.6(2) . . ? C7 C2 C3 118.6(2) . . ? N1 C2 C3 118.8(2) . . ? C4 C3 C2 119.5(2) . . ? C4 C3 C8 120.22(19) . . ? C2 C3 C8 120.0(2) . . ? C5 C4 C3 121.0(2) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 118.9(2) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 121.4(2) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C6 C7 C2 120.4(2) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? O2 C8 N2 119.82(19) . . ? O2 C8 C3 120.28(18) . . ? N2 C8 C3 119.86(18) . . ? N2 C9 C13 113.88(17) . . ? N2 C9 C10 103.32(17) . . ? C13 C9 C10 111.16(18) . . ? N2 C9 H9 109.4 . . ? C13 C9 H9 109.4 . . ? C10 C9 H9 109.4 . . ? C11 C10 C9 103.63(18) . . ? C11 C10 H10A 111.0 . . ? C9 C10 H10A 111.0 . . ? C11 C10 H10B 111.0 . . ? C9 C10 H10B 111.0 . . ? H10A C10 H10B 109.0 . . ? C12 C11 C10 103.30(18) . . ? C12 C11 H11A 111.1 . . ? C10 C11 H11A 111.1 . . ? C12 C11 H11B 111.1 . . ? C10 C11 H11B 111.1 . . ? H11A C11 H11B 109.1 . . ? N2 C12 C11 102.93(17) . . ? N2 C12 H12A 111.2 . . ? C11 C12 H12A 111.2 . . ? N2 C12 H12B 111.2 . . ? C11 C12 H12B 111.2 . . ? H12A C12 H12B 109.1 . . ? O3 C13 O4 125.00(19) . . ? O3 C13 C9 123.44(19) . . ? O4 C13 C9 111.32(17) . . ? O4 C14 C15' 123.7(4) . . ? O4 C14 C19 109.39(16) . . ? C15' C14 C19 105.4(4) . . ? O4 C14 C15 106.9(4) . . ? C19 C14 C15 102.3(3) . . ? O4 C14 H14 112.5 . . ? C15' C14 H14 92.3 . . ? C19 C14 H14 112.5 . . ? C15 C14 H14 112.5 . . ? C16 C15 C14 101.4(5) . . ? C16 C15 H15A 111.5 . . ? C14 C15 H15A 111.5 . . ? C16 C15 H15B 111.5 . . ? C14 C15 H15B 111.5 . . ? H15A C15 H15B 109.3 . . ? C15 C16 C17 105.5(8) . . ? C15 C16 C20 100.4(5) . . ? C17 C16 C20 107.3(6) . . ? C15 C16 H16 114.1 . . ? C17 C16 H16 114.2 . . ? C20 C16 H16 114.2 . . ? C18 C17 C16 97.3(7) . . ? C18 C17 H17A 112.3 . . ? C16 C17 H17A 112.3 . . ? C18 C17 H17B 112.3 . . ? C16 C17 H17B 112.3 . . ? H17A C17 H17B 109.9 . . ? C14 C15' C16' 102.2(8) . . ? C14 C15' H15C 111.3 . . ? C16' C15' H15C 111.3 . . ? C14 C15' H15D 111.3 . . ? C16' C15' H15D 111.3 . . ? H15C C15' H15D 109.2 . . ? C20 C16' C15' 106.3(7) . . ? C20 C16' C17' 99.0(7) . . ? C15' C16' C17' 108.2(7) . . ? C20 C16' H16' 114.0 . . ? C15' C16' H16' 114.0 . . ? C17' C16' H16' 114.0 . . ? C16' C17' C18 102.8(6) . . ? C16' C17' H17C 111.2 . . ? C18 C17' H17C 111.2 . . ? C16' C17' H17D 111.2 . . ? C18 C17' H17D 111.2 . . ? H17C C17' H17D 109.1 . . ? C17 C18 C19 116.7(5) . . ? C19 C18 C17' 95.0(4) . . ? C17 C18 H18A 108.1 . . ? C19 C18 H18A 108.1 . . ? C17' C18 H18A 110.8 . . ? C17 C18 H18B 108.1 . . ? C19 C18 H18B 108.1 . . ? C17' C18 H18B 125.8 . . ? H18A C18 H18B 107.3 . . ? C23 C19 C18 113.9(2) . . ? C23 C19 C14 113.09(19) . . ? C18 C19 C14 108.4(2) . . ? C23 C19 C20 117.0(2) . . ? C18 C19 C20 102.3(2) . . ? C14 C19 C20 100.72(17) . . ? C16' C20 C22 86.8(6) . . ? C16' C20 C21 119.0(4) . . ? C22 C20 C21 109.3(5) . . ? C16' C20 C19 98.3(4) . . ? C22 C20 C19 126.1(5) . . ? C21 C20 C19 114.2(2) . . ? C16' C20 C22' 111.8(4) . . ? C21 C20 C22' 104.6(3) . . ? C19 C20 C22' 108.8(3) . . ? C22 C20 C16 107.4(6) . . ? C21 C20 C16 110.5(4) . . ? C19 C20 C16 85.9(4) . . ? C22' C20 C16 131.8(4) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? C20 C22' H22D 109.5 . . ? C20 C22' H22E 109.5 . . ? H22D C22' H22E 109.5 . . ? C20 C22' H22F 109.5 . . ? H22D C22' H22F 109.5 . . ? H22E C22' H22F 109.5 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O5 C24 C25 109.8(2) . . ? O5 C24 H24A 109.7 . . ? C25 C24 H24A 109.7 . . ? O5 C24 H24B 109.7 . . ? C25 C24 H24B 109.7 . . ? H24A C24 H24B 108.2 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C1 N1 C2 127.0(2) . . ? C1 N1 H1 116.5 . . ? C2 N1 H1 116.5 . . ? C8 N2 C9 117.96(17) . . ? C8 N2 C12 128.96(17) . . ? C9 N2 C12 112.07(16) . . ? C13 O4 C14 116.41(16) . . ? C1 O5 C24 115.96(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 C2 C3 C4 -3.1(3) . . . . ? N1 C2 C3 C4 175.7(2) . . . . ? C7 C2 C3 C8 -178.0(2) . . . . ? N1 C2 C3 C8 0.8(3) . . . . ? C2 C3 C4 C5 1.1(3) . . . . ? C8 C3 C4 C5 175.9(2) . . . . ? C3 C4 C5 C6 1.5(4) . . . . ? C4 C5 C6 C7 -2.0(4) . . . . ? C5 C6 C7 C2 -0.1(4) . . . . ? N1 C2 C7 C6 -176.1(3) . . . . ? C3 C2 C7 C6 2.7(4) . . . . ? C4 C3 C8 O2 -136.9(2) . . . . ? C2 C3 C8 O2 38.0(3) . . . . ? C4 C3 C8 N2 40.8(3) . . . . ? C2 C3 C8 N2 -144.4(2) . . . . ? N2 C9 C10 C11 28.5(2) . . . . ? C13 C9 C10 C11 -94.1(2) . . . . ? C9 C10 C11 C12 -38.7(2) . . . . ? C10 C11 C12 N2 33.2(2) . . . . ? N2 C9 C13 O3 147.1(2) . . . . ? C10 C9 C13 O3 -96.7(2) . . . . ? N2 C9 C13 O4 -38.3(2) . . . . ? C10 C9 C13 O4 77.9(2) . . . . ? O4 C14 C15 C16 -121.2(6) . . . . ? C15' C14 C15 C16 95(2) . . . . ? C19 C14 C15 C16 -6.3(6) . . . . ? C14 C15 C16 C17 78.0(7) . . . . ? C14 C15 C16 C20 -33.3(7) . . . . ? C15 C16 C17 C18 -76.1(8) . . . . ? C20 C16 C17 C18 30.3(8) . . . . ? O4 C14 C15' C16' -126.4(4) . . . . ? C19 C14 C15' C16' 0.3(6) . . . . ? C15 C14 C15' C16' -84.0(19) . . . . ? C14 C15' C16' C20 -33.5(7) . . . . ? C14 C15' C16' C17' 72.0(8) . . . . ? C20 C16' C17' C18 39.9(6) . . . . ? C15' C16' C17' C18 -70.6(8) . . . . ? C16 C17 C18 C19 3.9(8) . . . . ? C16 C17 C18 C17' -17.5(15) . . . . ? C16' C17' C18 C17 159(2) . . . . ? C16' C17' C18 C19 -1.6(6) . . . . ? C17 C18 C19 C23 -167.8(6) . . . . ? C17' C18 C19 C23 -159.6(3) . . . . ? C17 C18 C19 C14 65.3(6) . . . . ? C17' C18 C19 C14 73.6(4) . . . . ? C17 C18 C19 C20 -40.6(6) . . . . ? C17' C18 C19 C20 -32.3(4) . . . . ? O4 C14 C19 C23 -71.5(3) . . . . ? C15' C14 C19 C23 153.5(4) . . . . ? C15 C14 C19 C23 175.4(4) . . . . ? O4 C14 C19 C18 55.8(3) . . . . ? C15' C14 C19 C18 -79.1(4) . . . . ? C15 C14 C19 C18 -57.3(4) . . . . ? O4 C14 C19 C20 162.8(2) . . . . ? C15' C14 C19 C20 27.9(4) . . . . ? C15 C14 C19 C20 49.7(4) . . . . ? C15' C16' C20 C22 -75.7(7) . . . . ? C17' C16' C20 C22 172.3(7) . . . . ? C15' C16' C20 C21 174.0(5) . . . . ? C17' C16' C20 C21 62.0(6) . . . . ? C15' C16' C20 C19 50.3(6) . . . . ? C17' C16' C20 C19 -61.7(5) . . . . ? C15' C16' C20 C22' -63.8(7) . . . . ? C17' C16' C20 C22' -175.8(5) . . . . ? C15' C16' C20 C16 103.9(16) . . . . ? C17' C16' C20 C16 -8.1(12) . . . . ? C23 C19 C20 C16' -171.1(4) . . . . ? C18 C19 C20 C16' 63.7(4) . . . . ? C14 C19 C20 C16' -48.1(4) . . . . ? C23 C19 C20 C22 -78.9(6) . . . . ? C18 C19 C20 C22 155.8(6) . . . . ? C14 C19 C20 C22 44.1(6) . . . . ? C23 C19 C20 C21 61.9(3) . . . . ? C18 C19 C20 C21 -63.4(3) . . . . ? C14 C19 C20 C21 -175.2(3) . . . . ? C23 C19 C20 C22' -54.5(4) . . . . ? C18 C19 C20 C22' -179.8(3) . . . . ? C14 C19 C20 C22' 68.5(3) . . . . ? C23 C19 C20 C16 172.5(4) . . . . ? C18 C19 C20 C16 47.3(4) . . . . ? C14 C19 C20 C16 -64.5(3) . . . . ? C15 C16 C20 C16' -67.1(14) . . . . ? C17 C16 C20 C16' -177.0(19) . . . . ? C15 C16 C20 C22 -66.7(7) . . . . ? C17 C16 C20 C22 -176.6(7) . . . . ? C15 C16 C20 C21 174.2(5) . . . . ? C17 C16 C20 C21 64.3(7) . . . . ? C15 C16 C20 C19 59.9(6) . . . . ? C17 C16 C20 C19 -50.0(6) . . . . ? C15 C16 C20 C22' -51.8(8) . . . . ? C17 C16 C20 C22' -161.7(6) . . . . ? O1 C1 N1 C2 -4.6(5) . . . . ? O5 C1 N1 C2 175.3(2) . . . . ? C7 C2 N1 C1 -13.8(4) . . . . ? C3 C2 N1 C1 167.5(2) . . . . ? O2 C8 N2 C9 2.2(3) . . . . ? C3 C8 N2 C9 -175.46(18) . . . . ? O2 C8 N2 C12 -165.3(2) . . . . ? C3 C8 N2 C12 17.1(3) . . . . ? C13 C9 N2 C8 -56.7(2) . . . . ? C10 C9 N2 C8 -177.37(19) . . . . ? C13 C9 N2 C12 112.8(2) . . . . ? C10 C9 N2 C12 -7.9(2) . . . . ? C11 C12 N2 C8 152.1(2) . . . . ? C11 C12 N2 C9 -16.0(2) . . . . ? O3 C13 O4 C14 4.6(3) . . . . ? C9 C13 O4 C14 -169.88(17) . . . . ? C15' C14 O4 C13 -69.6(6) . . . . ? C19 C14 O4 C13 165.45(17) . . . . ? C15 C14 O4 C13 -84.5(4) . . . . ? O1 C1 O5 C24 6.0(4) . . . . ? N1 C1 O5 C24 -173.9(2) . . . . ? C25 C24 O5 C1 89.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.195 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 874045' ####################################################################### # # 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_10 #TrackingRef '10447_web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1333099354.peptide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 N2 O5' _chemical_formula_sum 'C18 H24 N2 O5' _chemical_formula_weight 348.39 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.3515(8) _cell_length_b 9.6398(9) _cell_length_c 22.979(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1850.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2758 _cell_measurement_theta_min 2.594 _cell_measurement_theta_max 22.041 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9608 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details "Bruker's SADABS" _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9400 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3251 _reflns_number_gt 2755 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.1371P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.9(13) _refine_ls_number_reflns 3251 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1861(2) 1.1077(2) 0.92159(9) 0.0847(6) Uani 1 1 d . . . O2 O 0.5965(2) 0.83649(14) 0.82142(7) 0.0552(4) Uani 1 1 d . . . O3 O 0.9204(2) 0.76259(17) 0.74818(8) 0.0669(5) Uani 1 1 d . . . O4 O 0.7173(2) 0.62080(14) 0.72741(7) 0.0530(4) Uani 1 1 d . . . O5 O 0.1578(2) 0.88172(18) 0.89767(8) 0.0680(5) Uani 1 1 d . . . N1 N 0.3984(2) 0.9753(2) 0.89446(8) 0.0534(5) Uani 1 1 d . . . H1 H 0.4262 0.8911 0.8873 0.064 Uiso 1 1 calc R . . N2 N 0.67790(19) 0.97692(16) 0.75026(8) 0.0438(4) Uani 1 1 d . . . C1 C 0.2421(3) 0.9997(3) 0.90646(10) 0.0570(6) Uani 1 1 d . . . C2 C 0.5185(3) 1.0776(2) 0.89278(9) 0.0486(5) Uani 1 1 d . . . C3 C 0.6344(3) 1.0725(2) 0.84828(9) 0.0451(5) Uani 1 1 d . . . C4 C 0.7559(3) 1.1711(2) 0.84807(11) 0.0565(6) Uani 1 1 d . . . H4 H 0.8337 1.1685 0.8191 0.068 Uiso 1 1 calc R . . C5 C 0.7626(4) 1.2729(3) 0.89042(13) 0.0722(8) Uani 1 1 d . . . H5 H 0.8439 1.3388 0.8896 0.087 Uiso 1 1 calc R . . C6 C 0.6496(4) 1.2767(3) 0.93337(12) 0.0740(8) Uani 1 1 d . . . H6 H 0.6551 1.3445 0.9621 0.089 Uiso 1 1 calc R . . C7 C 0.5273(4) 1.1802(3) 0.93440(11) 0.0651(7) Uani 1 1 d . . . H7 H 0.4501 1.1845 0.9635 0.078 Uiso 1 1 calc R . . C8 C 0.6332(2) 0.9552(2) 0.80546(9) 0.0438(5) Uani 1 1 d . . . C9 C 0.6770(3) 0.8583(2) 0.70995(9) 0.0456(5) Uani 1 1 d . . . H9 H 0.5677 0.8226 0.7060 0.055 Uiso 1 1 calc R . . C10 C 0.7305(3) 0.9229(2) 0.65281(10) 0.0587(6) Uani 1 1 d . . . H10A H 0.8463 0.9264 0.6501 0.070 Uiso 1 1 calc R . . H10B H 0.6885 0.8719 0.6198 0.070 Uiso 1 1 calc R . . C11 C 0.6592(4) 1.0672(2) 0.65612(10) 0.0622(7) Uani 1 1 d . . . H11A H 0.5452 1.0655 0.6482 0.075 Uiso 1 1 calc R . . H11B H 0.7110 1.1295 0.6288 0.075 Uiso 1 1 calc R . . C12 C 0.6925(3) 1.1099(2) 0.71846(10) 0.0536(6) Uani 1 1 d . . . H12A H 0.7990 1.1488 0.7225 0.064 Uiso 1 1 calc R . . H12B H 0.6144 1.1770 0.7321 0.064 Uiso 1 1 calc R . . C13 C 0.7863(3) 0.7443(2) 0.73142(9) 0.0456(5) Uani 1 1 d . . . C14 C 0.8102(3) 0.5050(2) 0.74742(13) 0.0735(7) Uani 1 1 d . . . H14A H 0.8222 0.5103 0.7889 0.110 Uiso 1 1 calc R . . H14B H 0.9139 0.5071 0.7294 0.110 Uiso 1 1 calc R . . H14C H 0.7567 0.4202 0.7373 0.110 Uiso 1 1 calc R . . C15 C -0.0167(3) 0.8915(4) 0.89846(15) 0.0853(9) Uani 1 1 d . . . H15A H -0.0584 0.8640 0.8608 0.102 Uiso 1 1 calc R . . H15B H -0.0477 0.9872 0.9052 0.102 Uiso 1 1 calc R . . C16 C -0.0884(5) 0.8027(4) 0.94405(14) 0.0915(10) Uani 1 1 d . . . H16 H -0.2043 0.8124 0.9388 0.110 Uiso 1 1 calc R . . C17 C -0.0575(7) 0.8553(5) 1.00174(18) 0.161(2) Uani 1 1 d . . . H17A H -0.0792 0.9531 1.0027 0.242 Uiso 1 1 calc R . . H17B H 0.0526 0.8393 1.0117 0.242 Uiso 1 1 calc R . . H17C H -0.1254 0.8086 1.0292 0.242 Uiso 1 1 calc R . . C18 C -0.0565(7) 0.6545(4) 0.9361(2) 0.1415(18) Uani 1 1 d . . . H18A H -0.1334 0.6015 0.9577 0.212 Uiso 1 1 calc R . . H18B H 0.0493 0.6334 0.9498 0.212 Uiso 1 1 calc R . . H18C H -0.0644 0.6316 0.8955 0.212 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 0.0733(14) 0.0698(13) 0.1110(16) -0.0161(11) 0.0232(12) 0.0090(11) O2 0.0664(11) 0.0349(7) 0.0644(9) -0.0007(7) 0.0114(8) -0.0046(7) O3 0.0458(9) 0.0504(9) 0.1044(13) -0.0092(9) -0.0093(10) 0.0039(8) O4 0.0609(10) 0.0309(7) 0.0673(9) -0.0030(7) -0.0077(8) 0.0006(7) O5 0.0570(11) 0.0625(11) 0.0846(12) 0.0077(9) 0.0103(9) -0.0049(9) N1 0.0520(12) 0.0481(10) 0.0602(11) 0.0005(9) 0.0055(9) 0.0038(9) N2 0.0458(10) 0.0302(8) 0.0553(10) -0.0012(7) 0.0051(8) 0.0029(8) C1 0.0631(15) 0.0560(14) 0.0519(13) 0.0053(11) 0.0123(11) 0.0067(13) C2 0.0540(14) 0.0437(11) 0.0482(11) 0.0009(10) -0.0034(10) 0.0040(10) C3 0.0461(13) 0.0367(10) 0.0524(12) -0.0003(9) -0.0047(10) 0.0053(9) C4 0.0503(14) 0.0484(12) 0.0708(15) -0.0039(12) -0.0025(12) -0.0038(11) C5 0.0713(18) 0.0555(15) 0.090(2) -0.0158(14) -0.0172(16) -0.0121(14) C6 0.092(2) 0.0653(17) 0.0644(16) -0.0223(13) -0.0099(15) -0.0012(16) C7 0.0741(19) 0.0666(16) 0.0548(14) -0.0119(13) -0.0016(12) 0.0016(15) C8 0.0355(11) 0.0374(11) 0.0586(13) -0.0012(9) 0.0011(9) 0.0003(9) C9 0.0446(13) 0.0350(10) 0.0572(13) -0.0043(9) -0.0013(10) -0.0007(9) C10 0.0721(17) 0.0470(12) 0.0570(14) -0.0052(10) 0.0054(12) -0.0008(12) C11 0.0760(18) 0.0490(13) 0.0617(15) 0.0108(11) 0.0005(13) 0.0008(12) C12 0.0593(16) 0.0349(10) 0.0667(14) 0.0052(10) 0.0057(12) 0.0045(11) C13 0.0446(13) 0.0380(11) 0.0541(12) -0.0075(9) 0.0045(10) 0.0003(10) C14 0.096(2) 0.0394(13) 0.0856(18) 0.0036(12) -0.0143(16) 0.0107(14) C15 0.0559(18) 0.101(2) 0.100(2) 0.011(2) 0.0077(15) -0.0068(17) C16 0.093(2) 0.093(2) 0.088(2) -0.0034(18) 0.0340(18) -0.016(2) C17 0.227(6) 0.161(4) 0.096(3) -0.011(3) 0.043(3) -0.050(5) C18 0.162(5) 0.084(3) 0.179(4) -0.004(3) 0.061(4) -0.026(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 C1 1.193(3) . ? O2 C8 1.240(2) . ? O3 C13 1.198(3) . ? O4 C13 1.326(2) . ? O4 C14 1.435(3) . ? O5 C1 1.352(3) . ? O5 C15 1.461(3) . ? N1 C1 1.354(3) . ? N1 C2 1.408(3) . ? N1 H1 0.8600 . ? N2 C8 1.339(3) . ? N2 C9 1.471(2) . ? N2 C12 1.481(3) . ? C2 C7 1.377(3) . ? C2 C3 1.409(3) . ? C3 C4 1.390(3) . ? C3 C8 1.499(3) . ? C4 C5 1.384(3) . ? C4 H4 0.9300 . ? C5 C6 1.366(4) . ? C5 H5 0.9300 . ? C6 C7 1.382(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 C13 1.511(3) . ? C9 C10 1.520(3) . ? C9 H9 0.9800 . ? C10 C11 1.515(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.516(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.479(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.442(5) . ? C16 C18 1.465(5) . ? C16 H16 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 C13 O4 C14 116.16(18) . . ? C1 O5 C15 117.6(2) . . ? C1 N1 C2 124.8(2) . . ? C1 N1 H1 117.6 . . ? C2 N1 H1 117.6 . . ? C8 N2 C9 118.28(16) . . ? C8 N2 C12 128.75(17) . . ? C9 N2 C12 111.24(17) . . ? O1 C1 O5 124.9(3) . . ? O1 C1 N1 126.1(3) . . ? O5 C1 N1 109.0(2) . . ? C7 C2 N1 121.4(2) . . ? C7 C2 C3 119.5(2) . . ? N1 C2 C3 119.00(19) . . ? C4 C3 C2 118.7(2) . . ? C4 C3 C8 121.2(2) . . ? C2 C3 C8 119.9(2) . . ? C5 C4 C3 120.8(2) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 120.0(3) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 120.3(2) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C2 C7 C6 120.7(3) . . ? C2 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? O2 C8 N2 119.56(18) . . ? O2 C8 C3 120.2(2) . . ? N2 C8 C3 120.16(18) . . ? N2 C9 C13 110.90(17) . . ? N2 C9 C10 102.96(16) . . ? C13 C9 C10 113.75(19) . . ? N2 C9 H9 109.7 . . ? C13 C9 H9 109.7 . . ? C10 C9 H9 109.7 . . ? C11 C10 C9 102.55(18) . . ? C11 C10 H10A 111.3 . . ? C9 C10 H10A 111.3 . . ? C11 C10 H10B 111.3 . . ? C9 C10 H10B 111.3 . . ? H10A C10 H10B 109.2 . . ? C10 C11 C12 103.00(19) . . ? C10 C11 H11A 111.2 . . ? C12 C11 H11A 111.2 . . ? C10 C11 H11B 111.2 . . ? C12 C11 H11B 111.2 . . ? H11A C11 H11B 109.1 . . ? N2 C12 C11 102.48(17) . . ? N2 C12 H12A 111.3 . . ? C11 C12 H12A 111.3 . . ? N2 C12 H12B 111.3 . . ? C11 C12 H12B 111.3 . . ? H12A C12 H12B 109.2 . . ? O3 C13 O4 124.1(2) . . ? O3 C13 C9 124.2(2) . . ? O4 C13 C9 111.61(19) . . ? O4 C14 H14A 109.5 . . ? O4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O5 C15 C16 112.0(3) . . ? O5 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? O5 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C18 115.2(4) . . ? C17 C16 C15 112.1(3) . . ? C18 C16 C15 113.7(3) . . ? C17 C16 H16 104.9 . . ? C18 C16 H16 104.9 . . ? C15 C16 H16 104.9 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 O5 C1 O1 9.4(4) . . . . ? C15 O5 C1 N1 -169.7(2) . . . . ? C2 N1 C1 O1 -6.2(4) . . . . ? C2 N1 C1 O5 172.9(2) . . . . ? C1 N1 C2 C7 43.0(3) . . . . ? C1 N1 C2 C3 -138.7(2) . . . . ? C7 C2 C3 C4 0.6(3) . . . . ? N1 C2 C3 C4 -177.81(19) . . . . ? C7 C2 C3 C8 175.4(2) . . . . ? N1 C2 C3 C8 -3.0(3) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C8 C3 C4 C5 -175.2(2) . . . . ? C3 C4 C5 C6 0.6(4) . . . . ? C4 C5 C6 C7 -0.8(4) . . . . ? N1 C2 C7 C6 177.5(2) . . . . ? C3 C2 C7 C6 -0.9(4) . . . . ? C5 C6 C7 C2 1.0(4) . . . . ? C9 N2 C8 O2 1.8(3) . . . . ? C12 N2 C8 O2 165.4(2) . . . . ? C9 N2 C8 C3 179.15(19) . . . . ? C12 N2 C8 C3 -17.2(3) . . . . ? C4 C3 C8 O2 138.3(2) . . . . ? C2 C3 C8 O2 -36.4(3) . . . . ? C4 C3 C8 N2 -39.1(3) . . . . ? C2 C3 C8 N2 146.3(2) . . . . ? C8 N2 C9 C13 -59.0(2) . . . . ? C12 N2 C9 C13 134.67(19) . . . . ? C8 N2 C9 C10 178.99(19) . . . . ? C12 N2 C9 C10 12.6(2) . . . . ? N2 C9 C10 C11 -33.6(2) . . . . ? C13 C9 C10 C11 -153.7(2) . . . . ? C9 C10 C11 C12 42.6(3) . . . . ? C8 N2 C12 C11 -151.1(2) . . . . ? C9 N2 C12 C11 13.4(2) . . . . ? C10 C11 C12 N2 -34.2(3) . . . . ? C14 O4 C13 O3 3.1(3) . . . . ? C14 O4 C13 C9 -179.22(19) . . . . ? N2 C9 C13 O3 -47.5(3) . . . . ? C10 C9 C13 O3 68.0(3) . . . . ? N2 C9 C13 O4 134.81(19) . . . . ? C10 C9 C13 O4 -109.7(2) . . . . ? C1 O5 C15 C16 -120.5(3) . . . . ? O5 C15 C16 C17 70.6(5) . . . . ? O5 C15 C16 C18 -62.1(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.314 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.034 _database_code_depnum_ccdc_archive 'CCDC 874046' ####################################################################### # # 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_11 #TrackingRef '10447_web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1333099354.peptide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H40 N4 O8' _chemical_formula_sum 'C40 H40 N4 O8' _chemical_formula_weight 704.76 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.173(5) _cell_length_b 13.001(8) _cell_length_c 17.350(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1843.5(19) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2147 _cell_measurement_theta_min 2.342 _cell_measurement_theta_max 21.001 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9787 _exptl_absorpt_correction_T_max 0.9978 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10075 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3616 _reflns_number_gt 2860 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.0085P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(15) _refine_ls_number_reflns 3616 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _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 0.8178(2) 0.94792(15) 0.61442(10) 0.0741(6) Uani 1 1 d . . . O2 O 0.4932(2) 0.74048(12) 0.80076(9) 0.0614(5) Uani 1 1 d . . . O3 O 0.8055(2) 0.68791(15) 0.89304(10) 0.0760(6) Uani 1 1 d . . . O4 O 0.6276(3) 0.67691(18) 0.99093(10) 0.0939(7) Uani 1 1 d . . . N1 N 0.7144(2) 0.82787(14) 0.69653(10) 0.0502(5) Uani 1 1 d . . . H1 H 0.7009 0.8154 0.7448 0.060 Uiso 1 1 calc R . . N2 N 0.5815(2) 0.57755(14) 0.80074(10) 0.0433(4) Uani 1 1 d . . . C1 C 0.7949(3) 0.91661(18) 0.67999(13) 0.0474(6) Uani 1 1 d . . . C2 C 0.6498(3) 0.75337(17) 0.64611(12) 0.0438(5) Uani 1 1 d . . . C3 C 0.5656(3) 0.67061(18) 0.67921(12) 0.0433(5) Uani 1 1 d . . . C4 C 0.4972(3) 0.5966(2) 0.63150(14) 0.0584(7) Uani 1 1 d . . . H4 H 0.4412 0.5414 0.6532 0.070 Uiso 1 1 calc R . . C5 C 0.5109(4) 0.6033(2) 0.55267(14) 0.0657(7) Uani 1 1 d . . . H5 H 0.4626 0.5540 0.5212 0.079 Uiso 1 1 calc R . . C6 C 0.5964(3) 0.6835(2) 0.52121(13) 0.0607(7) Uani 1 1 d . . . H6 H 0.6073 0.6876 0.4679 0.073 Uiso 1 1 calc R . . C7 C 0.6668(3) 0.75831(19) 0.56673(13) 0.0531(6) Uani 1 1 d . . . H7 H 0.7255 0.8118 0.5443 0.064 Uiso 1 1 calc R . . C8 C 0.5432(3) 0.66552(18) 0.76454(12) 0.0447(6) Uani 1 1 d . . . C9 C 0.5712(3) 0.57549(17) 0.88477(12) 0.0450(5) Uani 1 1 d . . . H9 H 0.4580 0.5869 0.9014 0.054 Uiso 1 1 calc R . . C10 C 0.6255(3) 0.46653(19) 0.90544(14) 0.0581(7) Uani 1 1 d . . . H10A H 0.6810 0.4654 0.9549 0.070 Uiso 1 1 calc R . . H10B H 0.5327 0.4201 0.9074 0.070 Uiso 1 1 calc R . . C11 C 0.7414(4) 0.4373(2) 0.84085(14) 0.0688(8) Uani 1 1 d . . . H11A H 0.8503 0.4640 0.8504 0.083 Uiso 1 1 calc R . . H11B H 0.7476 0.3632 0.8352 0.083 Uiso 1 1 calc R . . C12 C 0.6671(3) 0.48634(18) 0.76992(13) 0.0545(6) Uani 1 1 d . . . H12A H 0.7512 0.5061 0.7334 0.065 Uiso 1 1 calc R . . H12B H 0.5911 0.4398 0.7448 0.065 Uiso 1 1 calc R . . C13 C 0.6823(3) 0.6538(2) 0.92088(13) 0.0558(7) Uani 1 1 d . . . C14 C 0.7264(6) 0.7458(4) 1.0372(2) 0.168(2) Uani 1 1 d . . . H14A H 0.7338 0.8114 1.0122 0.253 Uiso 1 1 calc R . . H14B H 0.8341 0.7174 1.0432 0.253 Uiso 1 1 calc R . . H14C H 0.6769 0.7541 1.0870 0.253 Uiso 1 1 calc R . . C15 C 0.8529(3) 0.97652(18) 0.74840(13) 0.0468(6) Uani 1 1 d . . . C16 C 0.8812(3) 0.93299(19) 0.81981(13) 0.0567(7) Uani 1 1 d . . . H16 H 0.8607 0.8633 0.8273 0.068 Uiso 1 1 calc R . . C17 C 0.9395(3) 0.9915(2) 0.88006(16) 0.0727(8) Uani 1 1 d . . . H17 H 0.9586 0.9610 0.9277 0.087 Uiso 1 1 calc R . . C18 C 0.9694(3) 1.0946(2) 0.87010(18) 0.0711(8) Uani 1 1 d . . . H18 H 1.0082 1.1341 0.9109 0.085 Uiso 1 1 calc R . . C19 C 0.9417(3) 1.1386(2) 0.79970(19) 0.0732(8) Uani 1 1 d . . . H19 H 0.9618 1.2084 0.7928 0.088 Uiso 1 1 calc R . . C20 C 0.8845(3) 1.0808(2) 0.73898(16) 0.0611(7) Uani 1 1 d . . . H20 H 0.8668 1.1117 0.6914 0.073 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 0.0911(13) 0.0854(14) 0.0459(10) 0.0094(9) 0.0058(10) -0.0276(11) O2 0.0871(13) 0.0495(10) 0.0476(9) -0.0035(8) 0.0140(9) 0.0110(10) O3 0.0729(12) 0.0892(14) 0.0660(12) -0.0109(11) 0.0080(10) -0.0343(12) O4 0.1056(16) 0.1244(18) 0.0517(11) -0.0328(12) 0.0187(11) -0.0498(15) N1 0.0657(13) 0.0509(12) 0.0338(9) 0.0009(9) 0.0050(9) -0.0054(11) N2 0.0477(10) 0.0449(10) 0.0371(9) -0.0026(9) 0.0020(8) -0.0013(9) C1 0.0454(13) 0.0520(14) 0.0447(13) 0.0033(11) 0.0042(10) 0.0024(12) C2 0.0469(12) 0.0463(13) 0.0382(12) -0.0030(11) -0.0007(10) 0.0130(12) C3 0.0437(13) 0.0488(13) 0.0373(12) -0.0029(10) -0.0036(10) 0.0069(11) C4 0.0620(16) 0.0658(16) 0.0475(14) -0.0050(13) -0.0071(13) -0.0064(15) C5 0.0832(19) 0.0669(18) 0.0469(15) -0.0109(14) -0.0167(14) 0.0052(17) C6 0.0810(19) 0.0681(17) 0.0331(13) -0.0082(13) -0.0032(13) 0.0222(16) C7 0.0627(15) 0.0554(15) 0.0411(13) 0.0021(11) 0.0043(12) 0.0164(13) C8 0.0469(14) 0.0472(14) 0.0402(13) -0.0022(11) 0.0007(10) -0.0036(11) C9 0.0442(13) 0.0521(14) 0.0387(12) -0.0004(10) 0.0023(10) -0.0078(11) C10 0.0634(16) 0.0553(15) 0.0555(15) 0.0099(12) -0.0010(13) -0.0060(13) C11 0.0749(18) 0.0663(18) 0.0653(17) 0.0068(14) 0.0054(15) 0.0161(15) C12 0.0602(15) 0.0489(14) 0.0543(15) -0.0060(12) 0.0080(12) 0.0024(13) C13 0.0612(16) 0.0623(16) 0.0438(14) -0.0020(12) 0.0038(12) -0.0136(14) C14 0.187(5) 0.228(5) 0.090(3) -0.082(3) 0.021(3) -0.121(4) C15 0.0426(13) 0.0461(13) 0.0517(14) 0.0023(11) 0.0035(10) 0.0012(11) C16 0.0685(17) 0.0503(14) 0.0514(15) 0.0036(12) -0.0065(12) -0.0088(13) C17 0.089(2) 0.0695(19) 0.0602(17) -0.0026(15) -0.0166(15) -0.0103(17) C18 0.0702(18) 0.071(2) 0.0720(19) -0.0170(16) -0.0064(15) -0.0059(16) C19 0.076(2) 0.0510(16) 0.092(2) -0.0064(16) 0.0066(17) -0.0145(15) C20 0.0627(17) 0.0553(16) 0.0654(17) 0.0085(14) 0.0063(14) -0.0047(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.223(3) . ? O2 C8 1.230(3) . ? O3 C13 1.201(3) . ? O4 C13 1.329(3) . ? O4 C14 1.449(4) . ? N1 C1 1.359(3) . ? N1 C2 1.408(3) . ? N1 H1 0.8600 . ? N2 C8 1.342(3) . ? N2 C9 1.461(3) . ? N2 C12 1.477(3) . ? C1 C15 1.497(3) . ? C2 C7 1.386(3) . ? C2 C3 1.400(3) . ? C3 C4 1.387(3) . ? C3 C8 1.493(3) . ? C4 C5 1.375(3) . ? C4 H4 0.9300 . ? C5 C6 1.369(4) . ? C5 H5 0.9300 . ? C6 C7 1.379(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 C13 1.501(3) . ? C9 C10 1.527(3) . ? C9 H9 0.9800 . ? C10 C11 1.515(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.513(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.382(3) . ? C15 C20 1.390(3) . ? C16 C17 1.377(3) . ? C16 H16 0.9300 . ? C17 C18 1.374(4) . ? C17 H17 0.9300 . ? C18 C19 1.367(4) . ? C18 H18 0.9300 . ? C19 C20 1.376(4) . ? C19 H19 0.9300 . ? C20 H20 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 C13 O4 C14 117.3(3) . . ? C1 N1 C2 129.39(19) . . ? C1 N1 H1 115.3 . . ? C2 N1 H1 115.3 . . ? C8 N2 C9 117.99(19) . . ? C8 N2 C12 128.72(18) . . ? C9 N2 C12 111.97(18) . . ? O1 C1 N1 123.6(2) . . ? O1 C1 C15 121.1(2) . . ? N1 C1 C15 115.3(2) . . ? C7 C2 C3 119.5(2) . . ? C7 C2 N1 123.2(2) . . ? C3 C2 N1 117.26(19) . . ? C4 C3 C2 119.1(2) . . ? C4 C3 C8 120.7(2) . . ? C2 C3 C8 120.08(19) . . ? C5 C4 C3 121.1(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 119.1(3) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C7 121.5(2) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C6 C7 C2 119.6(2) . . ? C6 C7 H7 120.2 . . ? C2 C7 H7 120.2 . . ? O2 C8 N2 120.9(2) . . ? O2 C8 C3 120.8(2) . . ? N2 C8 C3 118.2(2) . . ? N2 C9 C13 111.65(19) . . ? N2 C9 C10 103.56(18) . . ? C13 C9 C10 110.8(2) . . ? N2 C9 H9 110.2 . . ? C13 C9 H9 110.2 . . ? C10 C9 H9 110.2 . . ? C11 C10 C9 103.9(2) . . ? C11 C10 H10A 111.0 . . ? C9 C10 H10A 111.0 . . ? C11 C10 H10B 111.0 . . ? C9 C10 H10B 111.0 . . ? H10A C10 H10B 109.0 . . ? C12 C11 C10 104.2(2) . . ? C12 C11 H11A 110.9 . . ? C10 C11 H11A 110.9 . . ? C12 C11 H11B 110.9 . . ? C10 C11 H11B 110.9 . . ? H11A C11 H11B 108.9 . . ? N2 C12 C11 103.52(18) . . ? N2 C12 H12A 111.1 . . ? C11 C12 H12A 111.1 . . ? N2 C12 H12B 111.1 . . ? C11 C12 H12B 111.1 . . ? H12A C12 H12B 109.0 . . ? O3 C13 O4 124.5(2) . . ? O3 C13 C9 126.1(2) . . ? O4 C13 C9 109.3(2) . . ? O4 C14 H14A 109.5 . . ? O4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 118.3(2) . . ? C16 C15 C1 123.4(2) . . ? C20 C15 C1 118.2(2) . . ? C17 C16 C15 120.8(2) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C18 C17 C16 120.3(3) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C19 C18 C17 119.4(3) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 120.8(3) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C19 C20 C15 120.4(3) . . ? C19 C20 H20 119.8 . . ? C15 C20 H20 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 3.3(4) . . . . ? C2 N1 C1 C15 -177.8(2) . . . . ? C1 N1 C2 C7 3.1(4) . . . . ? C1 N1 C2 C3 -177.3(2) . . . . ? C7 C2 C3 C4 -1.7(3) . . . . ? N1 C2 C3 C4 178.7(2) . . . . ? C7 C2 C3 C8 -178.7(2) . . . . ? N1 C2 C3 C8 1.8(3) . . . . ? C2 C3 C4 C5 0.0(4) . . . . ? C8 C3 C4 C5 176.9(2) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? C4 C5 C6 C7 -1.0(4) . . . . ? C5 C6 C7 C2 -0.7(4) . . . . ? C3 C2 C7 C6 2.0(3) . . . . ? N1 C2 C7 C6 -178.4(2) . . . . ? C9 N2 C8 O2 -3.5(3) . . . . ? C12 N2 C8 O2 -169.2(2) . . . . ? C9 N2 C8 C3 175.43(19) . . . . ? C12 N2 C8 C3 9.7(3) . . . . ? C4 C3 C8 O2 -128.5(3) . . . . ? C2 C3 C8 O2 48.4(3) . . . . ? C4 C3 C8 N2 52.6(3) . . . . ? C2 C3 C8 N2 -130.5(2) . . . . ? C8 N2 C9 C13 -59.7(3) . . . . ? C12 N2 C9 C13 108.3(2) . . . . ? C8 N2 C9 C10 -178.94(19) . . . . ? C12 N2 C9 C10 -10.9(3) . . . . ? N2 C9 C10 C11 28.9(2) . . . . ? C13 C9 C10 C11 -91.0(2) . . . . ? C9 C10 C11 C12 -36.4(3) . . . . ? C8 N2 C12 C11 155.0(2) . . . . ? C9 N2 C12 C11 -11.4(3) . . . . ? C10 C11 C12 N2 29.3(3) . . . . ? C14 O4 C13 O3 -1.8(5) . . . . ? C14 O4 C13 C9 175.4(3) . . . . ? N2 C9 C13 O3 -26.1(4) . . . . ? C10 C9 C13 O3 88.8(3) . . . . ? N2 C9 C13 O4 156.7(2) . . . . ? C10 C9 C13 O4 -88.4(3) . . . . ? O1 C1 C15 C16 -157.6(3) . . . . ? N1 C1 C15 C16 23.5(3) . . . . ? O1 C1 C15 C20 20.5(4) . . . . ? N1 C1 C15 C20 -158.4(2) . . . . ? C20 C15 C16 C17 -0.1(4) . . . . ? C1 C15 C16 C17 178.0(2) . . . . ? C15 C16 C17 C18 0.4(4) . . . . ? C16 C17 C18 C19 -0.3(5) . . . . ? C17 C18 C19 C20 -0.1(4) . . . . ? C18 C19 C20 C15 0.4(4) . . . . ? C16 C15 C20 C19 -0.3(4) . . . . ? C1 C15 C20 C19 -178.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.152 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.028 #===END _database_code_depnum_ccdc_archive 'CCDC 874047'