# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef 'Piv-Pro-Aib-Oxazine.CIF_1(2).txt' #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'Sep 22 13:22:53 2010' _audit_creation_method 'PLATON option' _audit_update_record ; 2010-10-05 # Formatted by publCIF ; #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name "'Dr. Erode N. Prabhakaran'" _publ_contact_author_address ; Department of Organic Chemistry Indian Institute of Science Bangalore, 560 012 India ; _publ_contact_author_email eprabhak@orgchem.iisc.ernet.in _publ_contact_author_fax '(91) 80 2360 0529' _publ_contact_author_phone '(91) 80 2293 3380' _publ_requested_coeditor_name ? _publ_contact_letter ; The manuscript has passed the checkcif tests and generates an acceptable printcif output. Yours sincerely Dr. Erode N. Prabhakaran. ; # #=============================================================================== # 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ; _journal_techeditor_code ? _journal_techeditor_notes ; ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Title (type here to add) ; _publ_section_title_footnote . # The loop structure below should contain the names and adresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Damodara N. Reddy' ; Department of Organic Chemistry Indian Institute of Science Bangalore 560 012, Karnataka India ; E.N.Prabhakaran ; Department of Organic Chemistry Indian Institute of Science Bangalore 560 012, Karnataka India ; #=============================================================================== # 4. TEXT _publ_section_synopsis . _publ_section_abstract ; (type here to add abstract) ; # Insert blank lines between paragraphs _publ_section_comment ; (type here to add) ; _publ_section_exptl_prep ; (type here to add preparation details) ; _publ_section_exptl_refinement ; (type here to add refinement details) ; # Insert blank lines between references _publ_section_references ; Bruker (2004). SMART (Version 5.628) and SAINT (Version 6.45a). BrukerAXS Inc., Madison, Wisconsin, USA. Farrugia, L. J. (1999). J. Appl. Cryst.32, 837--838. Sheldrick, G. M. (1997). SHELXL97. University of G\"ottingen, Germany. Spek, A. L. (2003). J. Appl. Cryst.36, 7--13. Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England. ; _publ_section_acknowledgements ; We thank the Department of Science and Technology, India, for use of the CCD facility setup under the IRHPA-DST program at IISc. ; _publ_section_figure_captions ; Fig. 1. View of the molecular structure of (I) showing the atom labelling scheme. Displacement ellipsoids are showed at the 50% probability level. H atoms are shown as small spheres of arbitrary radii. ; #=============================================================================== data_damu541_0m _database_code_depnum_ccdc_archive 'CCDC 797013' #TrackingRef 'Piv-Pro-Aib-Oxazine.CIF_1(2).txt' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point 410-411 _chemical_formula_moiety 'C17 H29 N3 O3' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C17 H29 N3 O3' _chemical_formula_iupac ? _chemical_formula_weight 323.43 _chemical_compound_source synthesized loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z _cell_length_a 10.100(5) _cell_length_b 10.997(5) _cell_length_c 16.768(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1862.4(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3668 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 26.00 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour 'color less' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.079 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Apex2 (Bruker)' _exptl_absorpt_correction_T_min 0.9766 _exptl_absorpt_correction_T_max 0.9843 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Brucker kappa apex2 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 15214 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3668 # number of observed reflections (> n sig(I)) _reflns_number_gt 2436 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker kappa Apex2' _computing_cell_refinement Apex2 _computing_data_reduction SAINT32 _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _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. ; _chemical_absolute_configuration rm _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^)+(0.0806P)^2^+0.0778P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 3668 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0883 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1541 _refine_ls_wR_factor_gt 0.1395 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.242 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.031 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 1.0299(3) 0.1382(3) 0.70322(17) 0.0560(8) Uani 1 1 d . . . H1 H 1.0617 0.2207 0.6923 0.067 Uiso 1 1 calc R . . C008 C 0.6756(3) 0.0455(3) 0.75944(16) 0.0520(7) Uani 1 1 d . . . C009 C 1.0733(3) 0.1698(3) 0.84367(19) 0.0616(8) Uani 1 1 d . . . C010 C 1.1287(4) 0.1328(4) 0.9258(2) 0.0839(8) Uani 1 1 d . . . C011 C 0.6587(3) -0.0350(3) 0.83213(17) 0.0536(7) Uani 1 1 d . . . C012 C 0.8808(3) 0.1373(3) 0.69895(16) 0.0527(7) Uani 1 1 d . . . C013 C 1.0888(4) 0.0506(3) 0.64103(19) 0.0695(9) Uani 1 1 d . . . H01A H 1.0256 -0.0123 0.6271 0.083 Uiso 1 1 calc R . . H01B H 1.1137 0.0941 0.5930 0.083 Uiso 1 1 calc R . . C014 C 1.1681(4) -0.0141(3) 0.76720(19) 0.0656(9) Uani 1 1 d . . . H01C H 1.1173 -0.0876 0.7766 0.079 Uiso 1 1 calc R . . H01D H 1.2448 -0.0137 0.8020 0.079 Uiso 1 1 calc R . . C015 C 1.2082(4) -0.0031(4) 0.6806(2) 0.0838(11) Uani 1 1 d . . . H01E H 1.2844 0.0497 0.6748 0.101 Uiso 1 1 calc R . . H01F H 1.2291 -0.0822 0.6583 0.101 Uiso 1 1 calc R . . C016 C 0.7301(4) -0.1396(4) 0.9469(2) 0.0855(12) Uani 1 1 d . . . H01G H 0.7324 -0.0889 0.9942 0.103 Uiso 1 1 calc R . . H01H H 0.8007 -0.1990 0.9514 0.103 Uiso 1 1 calc R . . C017 C 0.6009(4) 0.1639(3) 0.7726(2) 0.0812(10) Uani 1 1 d . . . H01I H 0.6309 0.2013 0.8210 0.122 Uiso 1 1 calc R . . H01J H 0.5078 0.1473 0.7764 0.122 Uiso 1 1 calc R . . H01K H 0.6169 0.2177 0.7286 0.122 Uiso 1 1 calc R . . C018 C 0.6255(4) -0.0215(4) 0.68477(19) 0.0807(11) Uani 1 1 d . . . H01L H 0.6387 0.0289 0.6387 0.121 Uiso 1 1 calc R . . H01M H 0.5330 -0.0391 0.6906 0.121 Uiso 1 1 calc R . . H01N H 0.6738 -0.0961 0.6784 0.121 Uiso 1 1 calc R . . C019 C 0.4945(4) -0.1296(4) 0.9137(2) 0.0861(12) Uani 1 1 d . . . H01O H 0.4182 -0.1810 0.9038 0.103 Uiso 1 1 calc R . . H01P H 0.4698 -0.0703 0.9539 0.103 Uiso 1 1 calc R . . C020 C 0.6023(5) -0.2039(4) 0.9442(3) 0.1038(14) Uani 1 1 d . . . H02A H 0.6114 -0.2754 0.9107 0.125 Uiso 1 1 calc R . . H02B H 0.5800 -0.2312 0.9975 0.125 Uiso 1 1 calc R . . C021 C 1.0975(4) -0.0009(4) 0.9478(2) 0.0839(8) Uani 1 1 d . . . H02C H 1.1136 -0.0134 1.0036 0.126 Uiso 1 1 calc R . . H02D H 1.1532 -0.0541 0.9172 0.126 Uiso 1 1 calc R . . H02E H 1.0064 -0.0180 0.9361 0.126 Uiso 1 1 calc R . . C022 C 1.2791(4) 0.1467(4) 0.9267(3) 0.1024(15) Uani 1 1 d . . . H02F H 1.3021 0.2294 0.9147 0.154 Uiso 1 1 calc R . . H02G H 1.3174 0.0937 0.8874 0.154 Uiso 1 1 calc R . . H02H H 1.3124 0.1256 0.9785 0.154 Uiso 1 1 calc R . . C023 C 1.0718(7) 0.2174(8) 0.9873(3) 0.200(4) Uani 1 1 d . . . H02I H 0.9788 0.2276 0.9778 0.301 Uiso 1 1 calc R . . H02J H 1.1153 0.2948 0.9839 0.301 Uiso 1 1 calc R . . H02K H 1.0851 0.1836 1.0395 0.301 Uiso 1 1 calc R . . N3 N 0.8182(2) 0.0671(2) 0.75246(15) 0.0597(7) Uani 1 1 d . . . H3 H 0.8677 0.0305 0.7867 0.072 Uiso 1 1 calc R . . N004 N 1.0857(2) 0.0965(2) 0.77894(14) 0.0513(6) Uani 1 1 d . . . N005 N 0.7547(3) -0.0634(3) 0.87677(16) 0.0709(8) Uani 1 1 d . . . O001 O 0.5289(2) -0.0667(2) 0.84109(14) 0.0721(7) Uani 1 1 d . . . O002 O 0.8230(2) 0.1947(2) 0.64601(12) 0.0709(7) Uani 1 1 d . . . O003 O 1.0129(3) 0.2663(2) 0.83620(16) 0.0921(9) 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 0.066(2) 0.0515(16) 0.0502(15) 0.0099(13) -0.0015(14) -0.0057(15) C008 0.0494(16) 0.0620(16) 0.0445(15) 0.0045(13) -0.0007(13) 0.0024(14) C009 0.0594(19) 0.0623(19) 0.0631(18) -0.0005(16) -0.0013(15) 0.0067(15) C010 0.0809(19) 0.104(2) 0.0664(15) 0.0104(15) -0.0073(14) 0.0046(18) C011 0.0506(17) 0.0593(17) 0.0510(16) -0.0002(14) -0.0006(15) 0.0031(14) C012 0.0605(19) 0.0532(16) 0.0443(14) 0.0058(14) 0.0001(13) -0.0003(15) C013 0.076(2) 0.075(2) 0.0576(19) 0.0046(16) 0.0148(17) -0.0031(19) C014 0.074(2) 0.0559(17) 0.067(2) -0.0009(16) -0.0042(17) 0.0123(17) C015 0.080(3) 0.094(3) 0.078(2) -0.009(2) 0.011(2) 0.020(2) C016 0.078(3) 0.105(3) 0.074(2) 0.038(2) -0.0063(19) -0.002(2) C017 0.085(3) 0.076(2) 0.082(2) 0.007(2) 0.014(2) 0.020(2) C018 0.084(3) 0.104(3) 0.054(2) -0.0094(19) -0.0075(17) -0.017(2) C019 0.074(3) 0.102(3) 0.082(2) 0.031(2) 0.0132(19) -0.006(2) C020 0.112(4) 0.107(3) 0.092(3) 0.034(3) 0.016(3) -0.006(3) C021 0.0809(19) 0.104(2) 0.0664(15) 0.0104(15) -0.0073(14) 0.0046(18) C022 0.092(3) 0.108(3) 0.108(3) 0.022(3) -0.044(2) -0.030(3) C023 0.256(8) 0.278(9) 0.067(3) -0.054(4) -0.024(4) 0.177(8) N3 0.0511(15) 0.0729(16) 0.0553(14) 0.0187(13) -0.0042(12) 0.0015(13) N004 0.0512(14) 0.0496(12) 0.0530(13) 0.0052(11) 0.0000(11) 0.0047(11) N005 0.0627(18) 0.089(2) 0.0611(15) 0.0218(15) -0.0029(14) -0.0010(15) O001 0.0557(13) 0.0938(16) 0.0668(13) 0.0191(13) 0.0040(11) -0.0075(12) O002 0.0713(15) 0.0803(15) 0.0610(13) 0.0206(12) -0.0071(11) 0.0034(12) O003 0.124(2) 0.0704(14) 0.0822(16) -0.0126(13) -0.0207(16) 0.0451(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N004 1.463(4) . ? C1 C012 1.507(4) . ? C1 C013 1.539(5) . ? C1 H1 0.9800 . ? C008 N3 1.465(4) . ? C008 C011 1.516(4) . ? C008 C017 1.521(4) . ? C008 C018 1.538(4) . ? C009 O003 1.230(4) . ? C009 N004 1.358(4) . ? C009 C010 1.542(5) . ? C010 C023 1.502(6) . ? C010 C022 1.526(6) . ? C010 C021 1.548(6) . ? C011 N005 1.264(4) . ? C011 O001 1.365(4) . ? C012 O002 1.236(3) . ? C012 N3 1.342(4) . ? C013 C015 1.498(5) . ? C013 H01A 0.9700 . ? C013 H01B 0.9700 . ? C014 N004 1.487(4) . ? C014 C015 1.512(5) . ? C014 H01C 0.9700 . ? C014 H01D 0.9700 . ? C015 H01E 0.9700 . ? C015 H01F 0.9700 . ? C016 N005 1.465(4) . ? C016 C020 1.472(6) . ? C016 H01G 0.9700 . ? C016 H01H 0.9700 . ? C017 H01I 0.9600 . ? C017 H01J 0.9600 . ? C017 H01K 0.9600 . ? C018 H01L 0.9600 . ? C018 H01M 0.9600 . ? C018 H01N 0.9600 . ? C019 O001 1.443(4) . ? C019 C020 1.454(6) . ? C019 H01O 0.9700 . ? C019 H01P 0.9700 . ? C020 H02A 0.9700 . ? C020 H02B 0.9700 . ? C021 H02C 0.9600 . ? C021 H02D 0.9600 . ? C021 H02E 0.9600 . ? C022 H02F 0.9600 . ? C022 H02G 0.9600 . ? C022 H02H 0.9600 . ? C023 H02I 0.9600 . ? C023 H02J 0.9600 . ? C023 H02K 0.9600 . ? N3 H3 0.8600 . ? 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 N004 C1 C012 115.1(3) . . ? N004 C1 C013 104.1(3) . . ? C012 C1 C013 110.5(3) . . ? N004 C1 H1 109.0 . . ? C012 C1 H1 109.0 . . ? C013 C1 H1 109.0 . . ? N3 C008 C011 105.6(2) . . ? N3 C008 C017 111.1(3) . . ? C011 C008 C017 109.1(2) . . ? N3 C008 C018 109.6(3) . . ? C011 C008 C018 109.8(3) . . ? C017 C008 C018 111.4(3) . . ? O003 C009 N004 118.4(3) . . ? O003 C009 C010 119.9(3) . . ? N004 C009 C010 121.6(3) . . ? C023 C010 C022 108.2(5) . . ? C023 C010 C009 108.1(4) . . ? C022 C010 C009 110.1(3) . . ? C023 C010 C021 110.3(5) . . ? C022 C010 C021 107.2(4) . . ? C009 C010 C021 112.9(3) . . ? N005 C011 O001 127.5(3) . . ? N005 C011 C008 122.3(3) . . ? O001 C011 C008 110.2(2) . . ? O002 C012 N3 123.5(3) . . ? O002 C012 C1 120.2(3) . . ? N3 C012 C1 116.3(3) . . ? C015 C013 C1 104.9(3) . . ? C015 C013 H01A 110.8 . . ? C1 C013 H01A 110.8 . . ? C015 C013 H01B 110.8 . . ? C1 C013 H01B 110.8 . . ? H01A C013 H01B 108.8 . . ? N004 C014 C015 102.2(3) . . ? N004 C014 H01C 111.3 . . ? C015 C014 H01C 111.3 . . ? N004 C014 H01D 111.3 . . ? C015 C014 H01D 111.3 . . ? H01C C014 H01D 109.2 . . ? C013 C015 C014 104.0(3) . . ? C013 C015 H01E 111.0 . . ? C014 C015 H01E 111.0 . . ? C013 C015 H01F 111.0 . . ? C014 C015 H01F 111.0 . . ? H01E C015 H01F 109.0 . . ? N005 C016 C020 113.5(3) . . ? N005 C016 H01G 108.9 . . ? C020 C016 H01G 108.9 . . ? N005 C016 H01H 108.9 . . ? C020 C016 H01H 108.9 . . ? H01G C016 H01H 107.7 . . ? C008 C017 H01I 109.5 . . ? C008 C017 H01J 109.5 . . ? H01I C017 H01J 109.5 . . ? C008 C017 H01K 109.5 . . ? H01I C017 H01K 109.5 . . ? H01J C017 H01K 109.5 . . ? C008 C018 H01L 109.5 . . ? C008 C018 H01M 109.5 . . ? H01L C018 H01M 109.5 . . ? C008 C018 H01N 109.5 . . ? H01L C018 H01N 109.5 . . ? H01M C018 H01N 109.5 . . ? O001 C019 C020 112.7(3) . . ? O001 C019 H01O 109.1 . . ? C020 C019 H01O 109.1 . . ? O001 C019 H01P 109.1 . . ? C020 C019 H01P 109.1 . . ? H01O C019 H01P 107.8 . . ? C019 C020 C016 113.4(4) . . ? C019 C020 H02A 108.9 . . ? C016 C020 H02A 108.9 . . ? C019 C020 H02B 108.9 . . ? C016 C020 H02B 108.9 . . ? H02A C020 H02B 107.7 . . ? C010 C021 H02C 109.5 . . ? C010 C021 H02D 109.5 . . ? H02C C021 H02D 109.5 . . ? C010 C021 H02E 109.5 . . ? H02C C021 H02E 109.5 . . ? H02D C021 H02E 109.5 . . ? C010 C022 H02F 109.5 . . ? C010 C022 H02G 109.5 . . ? H02F C022 H02G 109.5 . . ? C010 C022 H02H 109.5 . . ? H02F C022 H02H 109.5 . . ? H02G C022 H02H 109.5 . . ? C010 C023 H02I 109.5 . . ? C010 C023 H02J 109.5 . . ? H02I C023 H02J 109.5 . . ? C010 C023 H02K 109.5 . . ? H02I C023 H02K 109.5 . . ? H02J C023 H02K 109.5 . . ? C012 N3 C008 127.6(3) . . ? C012 N3 H3 116.2 . . ? C008 N3 H3 116.2 . . ? C009 N004 C1 118.2(2) . . ? C009 N004 C014 130.0(2) . . ? C1 N004 C014 110.9(2) . . ? C011 N005 C016 119.1(3) . . ? C011 O001 C019 116.5(3) . . ? 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 C019 O001 C011 C008 -171.9(3) . . . . no C019 O001 C011 N005 6.7(5) . . . . no C011 O001 C019 C020 -30.8(4) . . . . no C009 N004 C1 C013 167.3(3) . . . . no C014 N004 C1 C012 117.9(3) . . . . no C1 N004 C014 C015 24.5(3) . . . . no C009 N004 C014 C015 -144.4(3) . . . . no C1 N004 C009 O003 1.8(4) . . . . no C009 N004 C1 C012 -71.7(4) . . . . no C1 N004 C009 C010 179.8(3) . . . . no C014 N004 C1 C013 -3.1(3) . . . . no C014 N004 C009 C010 -12.0(5) . . . . no C014 N004 C009 O003 170.1(3) . . . . no C016 N005 C011 O001 0.4(5) . . . . no C016 N005 C011 C008 178.8(3) . . . . no C011 N005 C016 C020 17.1(5) . . . . no C008 N3 C012 C1 -177.2(3) . . . . no C012 N3 C008 C017 -58.9(4) . . . . no C012 N3 C008 C018 64.7(4) . . . . no C012 N3 C008 C011 -177.1(3) . . . . no C008 N3 C012 O002 -0.5(5) . . . . no C012 C1 C013 C015 -144.0(3) . . . . no C013 C1 C012 N3 98.2(3) . . . . no N004 C1 C012 O002 164.0(3) . . . . no N004 C1 C013 C015 -20.0(3) . . . . no C013 C1 C012 O002 -78.6(4) . . . . no N004 C1 C012 N3 -19.2(4) . . . . no C018 C008 C011 O001 -58.2(3) . . . . no N3 C008 C011 O001 -176.3(2) . . . . no C017 C008 C011 N005 -114.5(4) . . . . no C017 C008 C011 O001 64.1(3) . . . . no C018 C008 C011 N005 123.2(3) . . . . no N3 C008 C011 N005 5.1(4) . . . . no N004 C009 C010 C023 -166.8(4) . . . . no O003 C009 C010 C023 11.1(5) . . . . no N004 C009 C010 C022 75.2(4) . . . . no N004 C009 C010 C021 -44.6(4) . . . . no O003 C009 C010 C021 133.4(3) . . . . no O003 C009 C010 C022 -106.9(4) . . . . no C1 C013 C015 C014 35.2(4) . . . . no N004 C014 C015 C013 -36.2(3) . . . . no N005 C016 C020 C019 -41.0(5) . . . . no O001 C019 C020 C016 47.8(5) . . . . no #===END # Attachment 'Piv-Pro-Aib-amidopropylalcohol.cif_1(2).txt' # CIF-file generated for damu531_0m in P2(1) #============================================================================== #=============================================================================== data_damu531_0m _database_code_depnum_ccdc_archive 'CCDC 797014' #TrackingRef 'Piv-Pro-Aib-amidopropylalcohol.cif_1(2).txt' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point 442-443 _chemical_formula_moiety 'C17 H31 N3 O4' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C17 H31 N3 O4' _chemical_formula_iupac ? _chemical_formula_weight 341.45 _chemical_compound_source synthesized loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z _cell_length_a 6.031(5) _cell_length_b 8.634(5) _cell_length_c 18.780(5) _cell_angle_alpha 90 _cell_angle_beta 94.933(5) _cell_angle_gamma 90 _cell_volume 974.3(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3746 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 25.99 _cell_special_details ; ; _exptl_crystal_description ' block' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.083 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Apex2 (Bruker)' _exptl_absorpt_correction_T_min 0.9756 _exptl_absorpt_correction_T_max 0.9836 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Brucker kappa apex2 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 6176 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3746 # number of observed reflections (> n sig(I)) _reflns_number_gt 3005 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker kappa Apex2' _computing_cell_refinement Apex2 _computing_data_reduction SAINT32 _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _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. ; _chemical_absolute_configuration rm _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^)+(0.0688P)^2^+0.2547P] 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 2.0(17) _refine_ls_number_reflns 3746 _refine_ls_number_parameters 223 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0730 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1503 _refine_ls_wR_factor_gt 0.1401 _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 _refine_diff_density_max 0.571 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.040 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.3726(5) 0.3824(4) 0.80758(14) 0.0413(6) Uani 1 1 d . . . H1 H 0.2553 0.4610 0.8015 0.050 Uiso 1 1 calc R . . C2 C 0.3013(6) 0.2511(4) 0.85583(17) 0.0589(9) Uani 1 1 d . . . H2A H 0.4278 0.2113 0.8857 0.071 Uiso 1 1 calc R . . H2B H 0.1895 0.2867 0.8862 0.071 Uiso 1 1 calc R . . C3 C 0.2071(7) 0.1286(4) 0.80430(19) 0.0653(9) Uani 1 1 d . . . H3A H 0.2124 0.0271 0.8265 0.078 Uiso 1 1 calc R . . H3B H 0.0545 0.1521 0.7871 0.078 Uiso 1 1 calc R . . C4 C 0.3587(7) 0.1364(4) 0.74443(19) 0.0599(9) Uani 1 1 d . . . H4A H 0.4960 0.0801 0.7565 0.072 Uiso 1 1 calc R . . H4B H 0.2864 0.0950 0.7003 0.072 Uiso 1 1 calc R . . C5 C 0.4605(4) 0.3900(4) 0.68434(14) 0.0375(6) Uani 1 1 d . . . C6 C 0.4945(5) 0.3172(4) 0.61098(15) 0.0456(7) Uani 1 1 d . . . C7 C 0.6578(6) 0.1791(4) 0.6182(2) 0.0675(10) Uani 1 1 d . . . H7A H 0.5877 0.0931 0.6396 0.101 Uiso 1 1 calc R . . H7B H 0.7889 0.2086 0.6478 0.101 Uiso 1 1 calc R . . H7C H 0.6984 0.1499 0.5718 0.101 Uiso 1 1 calc R . . C8 C 0.5942(8) 0.4401(5) 0.5650(2) 0.0806(12) Uani 1 1 d . . . H8A H 0.6239 0.3956 0.5200 0.121 Uiso 1 1 calc R . . H8B H 0.7305 0.4777 0.5891 0.121 Uiso 1 1 calc R . . H8C H 0.4911 0.5243 0.5571 0.121 Uiso 1 1 calc R . . C9 C 0.2710(6) 0.2663(6) 0.57399(19) 0.0801(13) Uani 1 1 d . . . H9A H 0.1698 0.3523 0.5713 0.120 Uiso 1 1 calc R . . H9B H 0.2107 0.1840 0.6008 0.120 Uiso 1 1 calc R . . H9C H 0.2918 0.2305 0.5266 0.120 Uiso 1 1 calc R . . C10 C 1.1055(6) 0.7885(5) 0.60076(17) 0.0611(9) Uani 1 1 d . . . H10A H 1.0862 0.6859 0.5801 0.073 Uiso 1 1 calc R . . H10B H 1.0612 0.8633 0.5637 0.073 Uiso 1 1 calc R . . C11 C 0.9564(6) 0.8050(7) 0.6601(2) 0.0831(13) Uani 1 1 d . . . H11A H 0.9609 0.9119 0.6761 0.100 Uiso 1 1 calc R . . H11B H 0.8049 0.7827 0.6414 0.100 Uiso 1 1 calc R . . C12 C 1.0125(6) 0.7062(7) 0.7209(2) 0.0843(14) Uani 1 1 d . . . H12A H 1.1615 0.7319 0.7410 0.101 Uiso 1 1 calc R . . H12B H 1.0148 0.5997 0.7045 0.101 Uiso 1 1 calc R . . C13 C 0.9325(4) 0.7116(4) 0.84633(16) 0.0468(7) Uani 1 1 d . . . C14 C 0.7563(4) 0.6839(4) 0.89979(15) 0.0444(7) Uani 1 1 d . . . C15 C 0.6708(6) 0.8428(4) 0.9203(2) 0.0692(11) Uani 1 1 d . . . H15A H 0.6013 0.8930 0.8786 0.104 Uiso 1 1 calc R . . H15B H 0.7931 0.9046 0.9402 0.104 Uiso 1 1 calc R . . H15C H 0.5643 0.8306 0.9551 0.104 Uiso 1 1 calc R . . C16 C 0.8630(6) 0.6018(5) 0.96594(17) 0.0682(10) Uani 1 1 d . . . H16A H 0.7519 0.5817 0.9984 0.102 Uiso 1 1 calc R . . H16B H 0.9775 0.6663 0.9889 0.102 Uiso 1 1 calc R . . H16C H 0.9269 0.5056 0.9521 0.102 Uiso 1 1 calc R . . C17 C 0.5896(5) 0.4559(4) 0.83636(14) 0.0425(6) Uani 1 1 d . . . N1 N 0.4003(4) 0.3047(3) 0.73839(11) 0.0426(5) Uani 1 1 d . . . N2 N 0.5680(4) 0.5966(3) 0.86659(11) 0.0402(5) Uani 1 1 d . . . H2 H 0.4372 0.6364 0.8662 0.048 Uiso 1 1 calc R . . N3 N 0.8597(4) 0.7176(4) 0.77766(14) 0.0598(8) Uani 1 1 d . . . H3 H 0.7195 0.7284 0.7660 0.072 Uiso 1 1 calc R . . O1 O 0.4856(3) 0.5315(2) 0.69293(11) 0.0449(5) Uani 1 1 d . . . O2 O 0.7689(4) 0.3918(3) 0.83316(12) 0.0606(6) Uani 1 1 d . . . O3 O 1.1275(3) 0.7338(3) 0.86819(13) 0.0634(6) Uani 1 1 d . . . O4 O 1.3328(4) 0.8108(3) 0.62329(13) 0.0609(6) Uani 1 1 d . . . H4 H 1.3799 0.7355 0.6465 0.091 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0472(15) 0.0432(16) 0.0338(14) 0.0021(13) 0.0059(12) 0.0019(13) C2 0.069(2) 0.064(2) 0.0454(17) 0.0108(15) 0.0127(15) -0.0047(17) C3 0.079(2) 0.056(2) 0.063(2) 0.0117(17) 0.0159(18) -0.0147(18) C4 0.081(2) 0.0382(17) 0.062(2) -0.0021(15) 0.0137(17) -0.0127(16) C5 0.0360(13) 0.0403(16) 0.0359(14) 0.0002(12) 0.0017(11) -0.0002(12) C6 0.0460(15) 0.0541(18) 0.0375(14) -0.0060(14) 0.0076(12) 0.0044(14) C7 0.069(2) 0.066(2) 0.070(2) -0.0067(19) 0.0194(18) 0.0185(18) C8 0.115(3) 0.079(3) 0.053(2) 0.0008(19) 0.034(2) 0.009(2) C9 0.061(2) 0.125(4) 0.053(2) -0.032(2) -0.0045(17) 0.007(2) C10 0.0572(19) 0.078(3) 0.0478(18) 0.0127(18) 0.0027(15) -0.0073(18) C11 0.051(2) 0.132(4) 0.066(2) 0.016(3) 0.0020(17) -0.006(2) C12 0.056(2) 0.135(4) 0.063(2) 0.014(3) 0.0118(17) -0.003(2) C13 0.0358(14) 0.0527(18) 0.0513(17) -0.0083(15) 0.0009(12) 0.0010(13) C14 0.0357(14) 0.0571(19) 0.0393(15) -0.0121(13) -0.0032(11) 0.0031(13) C15 0.0516(19) 0.068(3) 0.088(3) -0.039(2) 0.0017(18) 0.0064(17) C16 0.066(2) 0.093(3) 0.0434(18) -0.0038(19) -0.0077(15) 0.002(2) C17 0.0485(16) 0.0455(16) 0.0334(14) 0.0021(13) 0.0032(11) 0.0031(14) N1 0.0569(14) 0.0354(12) 0.0360(12) -0.0025(10) 0.0078(10) -0.0030(11) N2 0.0348(11) 0.0477(14) 0.0383(12) -0.0074(10) 0.0037(9) 0.0046(10) N3 0.0369(13) 0.095(2) 0.0475(15) 0.0059(15) 0.0045(11) -0.0126(14) O1 0.0542(12) 0.0398(12) 0.0415(11) 0.0013(9) 0.0081(9) -0.0005(9) O2 0.0492(12) 0.0640(14) 0.0680(15) -0.0147(12) 0.0013(10) 0.0153(11) O3 0.0343(11) 0.0858(17) 0.0692(15) -0.0154(13) -0.0013(10) -0.0025(11) O4 0.0519(12) 0.0614(14) 0.0706(16) 0.0148(12) 0.0117(10) -0.0065(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 C1 N1 1.485(4) . ? C1 C17 1.512(4) . ? C1 C2 1.536(4) . ? C1 H1 0.9800 . ? C2 C3 1.511(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.511(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N1 1.481(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 O1 1.240(4) . ? C5 N1 1.330(3) . ? C5 C6 1.544(4) . ? C6 C8 1.524(5) . ? C6 C9 1.527(5) . ? C6 C7 1.545(5) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 O4 1.413(4) . ? C10 C11 1.498(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.442(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N3 1.472(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O3 1.227(3) . ? C13 N3 1.327(4) . ? C13 C14 1.542(4) . ? C14 N2 1.458(4) . ? C14 C16 1.524(4) . ? C14 C15 1.527(5) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O2 1.221(4) . ? C17 N2 1.352(4) . ? N2 H2 0.8600 . ? N3 H3 0.8600 . ? O4 H4 0.8200 . ? 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 N1 C1 C17 110.1(2) . . ? N1 C1 C2 103.9(2) . . ? C17 C1 C2 112.1(2) . . ? N1 C1 H1 110.2 . . ? C17 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? C3 C2 C1 104.4(2) . . ? C3 C2 H2A 110.9 . . ? C1 C2 H2A 110.9 . . ? C3 C2 H2B 110.9 . . ? C1 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? C4 C3 C2 103.1(3) . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3B 111.1 . . ? C2 C3 H3B 111.1 . . ? H3A C3 H3B 109.1 . . ? N1 C4 C3 102.6(3) . . ? N1 C4 H4A 111.2 . . ? C3 C4 H4A 111.2 . . ? N1 C4 H4B 111.2 . . ? C3 C4 H4B 111.2 . . ? H4A C4 H4B 109.2 . . ? O1 C5 N1 119.0(3) . . ? O1 C5 C6 119.6(3) . . ? N1 C5 C6 121.4(3) . . ? C8 C6 C9 108.6(3) . . ? C8 C6 C5 108.1(3) . . ? C9 C6 C5 110.1(2) . . ? C8 C6 C7 107.9(3) . . ? C9 C6 C7 110.5(3) . . ? C5 C6 C7 111.6(3) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O4 C10 C11 113.2(3) . . ? O4 C10 H10A 108.9 . . ? C11 C10 H10A 108.9 . . ? O4 C10 H10B 108.9 . . ? C11 C10 H10B 108.9 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 114.7(4) . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11B 108.6 . . ? C10 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C11 C12 N3 114.5(4) . . ? C11 C12 H12A 108.6 . . ? N3 C12 H12A 108.6 . . ? C11 C12 H12B 108.6 . . ? N3 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? O3 C13 N3 123.1(3) . . ? O3 C13 C14 120.0(3) . . ? N3 C13 C14 116.7(2) . . ? N2 C14 C16 111.5(3) . . ? N2 C14 C15 107.7(2) . . ? C16 C14 C15 109.9(3) . . ? N2 C14 C13 110.9(2) . . ? C16 C14 C13 109.7(3) . . ? C15 C14 C13 106.9(3) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 N2 123.1(3) . . ? O2 C17 C1 122.4(3) . . ? N2 C17 C1 114.6(2) . . ? C5 N1 C4 131.4(3) . . ? C5 N1 C1 118.5(2) . . ? C4 N1 C1 110.1(2) . . ? C17 N2 C14 123.0(2) . . ? C17 N2 H2 118.5 . . ? C14 N2 H2 118.5 . . ? C13 N3 C12 121.7(3) . . ? C13 N3 H3 119.1 . . ? C12 N3 H3 119.1 . . ? C10 O4 H4 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 N1 C1 C2 C3 -21.9(3) . . . . ? C17 C1 C2 C3 -140.8(3) . . . . ? C1 C2 C3 C4 37.7(4) . . . . ? C2 C3 C4 N1 -38.5(4) . . . . ? O1 C5 C6 C8 9.4(4) . . . . ? N1 C5 C6 C8 -171.9(3) . . . . ? O1 C5 C6 C9 -109.0(4) . . . . ? N1 C5 C6 C9 69.6(4) . . . . ? O1 C5 C6 C7 127.9(3) . . . . ? N1 C5 C6 C7 -53.4(4) . . . . ? O4 C10 C11 C12 -55.2(6) . . . . ? C10 C11 C12 N3 -177.4(4) . . . . ? O3 C13 C14 N2 -155.2(3) . . . . ? N3 C13 C14 N2 28.0(4) . . . . ? O3 C13 C14 C16 -31.6(4) . . . . ? N3 C13 C14 C16 151.6(3) . . . . ? O3 C13 C14 C15 87.5(4) . . . . ? N3 C13 C14 C15 -89.2(3) . . . . ? N1 C1 C17 O2 -41.0(4) . . . . ? C2 C1 C17 O2 74.2(3) . . . . ? N1 C1 C17 N2 139.9(2) . . . . ? C2 C1 C17 N2 -104.9(3) . . . . ? O1 C5 N1 C4 -179.8(3) . . . . ? C6 C5 N1 C4 1.5(5) . . . . ? O1 C5 N1 C1 -1.9(4) . . . . ? C6 C5 N1 C1 179.5(2) . . . . ? C3 C4 N1 C5 -156.5(3) . . . . ? C3 C4 N1 C1 25.5(4) . . . . ? C17 C1 N1 C5 -60.4(3) . . . . ? C2 C1 N1 C5 179.3(3) . . . . ? C17 C1 N1 C4 118.0(3) . . . . ? C2 C1 N1 C4 -2.3(3) . . . . ? O2 C17 N2 C14 -1.5(4) . . . . ? C1 C17 N2 C14 177.7(2) . . . . ? C16 C14 N2 C17 -65.4(3) . . . . ? C15 C14 N2 C17 173.9(3) . . . . ? C13 C14 N2 C17 57.2(3) . . . . ? O3 C13 N3 C12 18.1(6) . . . . ? C14 C13 N3 C12 -165.2(3) . . . . ? C11 C12 N3 C13 -142.0(4) . . . . ? #===END