# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year 2012 _publ_contact_author 'Stephen G. Davies' _publ_contact_author_phone '+44 1865 275695' _publ_contact_author_fax '+44 1865 275633' _publ_contact_author_email steve.davies@chem.ox.ac.uk loop_ _publ_author_name _publ_author_address S.G.Davies ; Department of Chemistry Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA U.K. ; E.M.Foster ; Department of Chemistry Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA U.K. ; A.B.Frost ; Department of Chemistry Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA U.K. ; J.A.Lee ; Department of Chemistry Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA U.K. ; P.M.Roberts ; Department of Chemistry Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA U.K. ; ; J.E.Thomson ; ; Department of Chemistry Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA U.K. ; _journal_volume ? _journal_page_first ? _journal_page_last ? _ccdc_journal_depnumbers ? _publ_section_title ; The curious effects of double asymmetric induction in the conjugate additions of the antipodes of lithium N-benzyl-(N-\a-methylbenzyl)amide to enantiopure cis- and trans-dioxolane containing \a,\b-unsaturated esters ; _publ_section_abstract ; The effects of "matching" and "mismatching" in the doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-(N-\a-methylbenzyl)amide to enantiopure cis- and trans-dioxolane containing \a,\b-unsaturated esters have been investigated. The levels of substrate control were established first upon conjugate addition of achiral lithium N-benzyl-N-isopropylamide to both tert-butyl (S,S,E)-4,5-O-isopropylidene-hex-2-enoate and tert-butyl (4R,5S,E)-4,5-O-isopropylidene-hex-2-enoate. However, upon conjugate addition of lithium (R)-N-benzyl-(N-\a-methylbenzyl)amide and lithium (S)-N-benzyl-(N-\a-methylbenzyl)amide to these substrates, neither reaction pairing reinforced the apparent sense of substrate control. These reactions do not, therefore, not conform to the doubly diastereoselective "matching" or "mismatching" pattern usually exhibited by this class of reaction. ; #============================================================================== data_57 _database_code_depnum_ccdc_archive 'CCDC 846621' #TrackingRef 'CrystallographicData.cif' _ccdc_journal_depnumber ? #============================================================================== _cell_length_a 22.1832(6) _cell_length_b 5.8375(2) _cell_length_c 14.5119(4) _cell_angle_alpha 90 _cell_angle_beta 105.8953(12) _cell_angle_gamma 90 _cell_volume 1807.36(9) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,y+1/2,z -x,y,-z -x+1/2,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C16 H32 N1 O4 # Dc = 1.11 Fooo = 664.00 Mu = 0.78 M = 302.43 # Found Formula = C16 H31 N1 O4 # Dc = 1.11 FOOO = 664.00 Mu = 0.78 M = 301.43 _chemical_formula_sum 'C16 H31 N1 O4' _chemical_formula_moiety 'C16 H31 N1 O4' _chemical_compound_source . _chemical_formula_weight 301.43 _cell_measurement_reflns_used 2239 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.140 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_max 0.900 _exptl_crystal_density_diffrn 1.108 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.078 # Sheldrick geometric approximatio 0.99 0.99 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 4052 _reflns_number_total 2239 _diffrn_reflns_av_R_equivalents 0.030 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 2239 # Theoretical number of reflections is about 4112 _diffrn_reflns_theta_min 5.410 _diffrn_reflns_theta_max 27.404 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.856 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -28 _reflns_limit_h_max 27 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 3.20 _oxford_diffrn_Wilson_scale 1.70 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.21 _refine_diff_density_max 0.33 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 2239 _refine_ls_number_restraints 1 _refine_ls_number_parameters 190 _oxford_refine_ls_R_factor_ref 0.0494 _refine_ls_wR_factor_ref 0.1210 _refine_ls_goodness_of_fit_ref 0.9701 _refine_ls_shift/su_max 0.0003891 _refine_ls_shift/su_mean 0.0000463 # The values computed from all data _oxford_reflns_number_all 2239 _refine_ls_R_factor_all 0.0494 _refine_ls_wR_factor_all 0.1210 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2088 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_gt 0.1165 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration (S,S,S) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 76.2 128. 79.5 34.3 8.30 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.53794(8) 0.1053(3) 0.84920(10) 0.0395 1.0000 Uani . . . . . . C2 C 0.54481(9) 0.2899(4) 0.88785(12) 0.0292 1.0000 Uani . . . . . . O3 O 0.58874(6) 0.3382(3) 0.97051(9) 0.0316 1.0000 Uani . . . . . . C4 C 0.63335(9) 0.1606(4) 1.02166(13) 0.0363 1.0000 Uani . . . . . . C5 C 0.67583(10) 0.2988(5) 1.10280(15) 0.0447 1.0000 Uani . . . . . . C6 C 0.59795(13) -0.0210(5) 1.06073(16) 0.0469 1.0000 Uani . . . . . . C7 C 0.67053(12) 0.0621(6) 0.95705(17) 0.0568 1.0000 Uani . . . . . . C8 C 0.50393(9) 0.4960(4) 0.85210(12) 0.0315 1.0000 Uani . . . . . . C9 C 0.49271(8) 0.5416(4) 0.74349(12) 0.0289 1.0000 Uani . . . . . . N10 N 0.54363(7) 0.6632(3) 0.71811(12) 0.0321 1.0000 Uani . . . . . . C11 C 0.60247(9) 0.5382(4) 0.72968(14) 0.0352 1.0000 Uani . . . . . . C12 C 0.65077(10) 0.7044(4) 0.71040(17) 0.0421 1.0000 Uani . . . . . . C13 C 0.59369(12) 0.3364(5) 0.6613(2) 0.0493 1.0000 Uani . . . . . . C14 C 0.43286(8) 0.6817(4) 0.70635(12) 0.0288 1.0000 Uani . . . . . . O15 O 0.38164(6) 0.5476(3) 0.71822(10) 0.0420 1.0000 Uani . . . . . . C16 C 0.32629(9) 0.6098(4) 0.64421(13) 0.0331 1.0000 Uani . . . . . . O17 O 0.34697(7) 0.7397(4) 0.57590(11) 0.0556 1.0000 Uani . . . . . . C18 C 0.41394(9) 0.7307(4) 0.59845(13) 0.0333 1.0000 Uani . . . . . . C19 C 0.43578(11) 0.9557(5) 0.56869(16) 0.0438 1.0000 Uani . . . . . . C20 C 0.29381(14) 0.3936(5) 0.6015(2) 0.0549 1.0000 Uani . . . . . . C21 C 0.28471(14) 0.7612(6) 0.68480(18) 0.0584 1.0000 Uani . . . . . . H51 H 0.7095 0.2034 1.1461 0.0645 1.0000 Uiso R . . . . . H52 H 0.6498 0.3664 1.1379 0.0637 1.0000 Uiso R . . . . . H53 H 0.6941 0.4169 1.0741 0.0634 1.0000 Uiso R . . . . . H61 H 0.6281 -0.1117 1.1088 0.0713 1.0000 Uiso R . . . . . H62 H 0.5687 0.0565 1.0909 0.0713 1.0000 Uiso R . . . . . H63 H 0.5753 -0.1174 1.0118 0.0714 1.0000 Uiso R . . . . . H71 H 0.7076 -0.0198 0.9954 0.0875 1.0000 Uiso R . . . . . H72 H 0.6861 0.1842 0.9236 0.0864 1.0000 Uiso R . . . . . H73 H 0.6436 -0.0424 0.9123 0.0872 1.0000 Uiso R . . . . . H82 H 0.5218 0.6368 0.8839 0.0360 1.0000 Uiso R . . . . . H81 H 0.4653 0.4670 0.8687 0.0377 1.0000 Uiso R . . . . . H91 H 0.4860 0.3957 0.7125 0.0334 1.0000 Uiso R . . . . . H111 H 0.6172 0.4835 0.7964 0.0416 1.0000 Uiso R . . . . . H121 H 0.6920 0.6310 0.7267 0.0628 1.0000 Uiso R . . . . . H122 H 0.6537 0.8378 0.7495 0.0641 1.0000 Uiso R . . . . . H123 H 0.6414 0.7465 0.6448 0.0627 1.0000 Uiso R . . . . . H133 H 0.6348 0.2646 0.6697 0.0719 1.0000 Uiso R . . . . . H132 H 0.5631 0.2254 0.6660 0.0720 1.0000 Uiso R . . . . . H131 H 0.5802 0.4021 0.6012 0.0716 1.0000 Uiso R . . . . . H141 H 0.4380 0.8302 0.7430 0.0342 1.0000 Uiso R . . . . . H181 H 0.4254 0.6042 0.5626 0.0394 1.0000 Uiso R . . . . . H191 H 0.4182 0.9720 0.5034 0.0628 1.0000 Uiso R . . . . . H192 H 0.4808 0.9528 0.5818 0.0631 1.0000 Uiso R . . . . . H193 H 0.4229 1.0788 0.6031 0.0652 1.0000 Uiso R . . . . . H202 H 0.2551 0.4346 0.5560 0.0805 1.0000 Uiso R . . . . . H201 H 0.2872 0.2993 0.6521 0.0811 1.0000 Uiso R . . . . . H203 H 0.3207 0.3128 0.5708 0.0821 1.0000 Uiso R . . . . . H212 H 0.2505 0.8143 0.6315 0.0860 1.0000 Uiso R . . . . . H211 H 0.3076 0.8870 0.7179 0.0873 1.0000 Uiso R . . . . . H213 H 0.2684 0.6704 0.7263 0.0859 1.0000 Uiso R . . . . . H101 H 0.5546 0.7800 0.7585 0.0372 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0478(8) 0.0341(8) 0.0317(7) -0.0031(6) 0.0030(6) 0.0016(7) C2 0.0287(8) 0.0344(10) 0.0232(7) -0.0010(8) 0.0052(6) -0.0007(8) O3 0.0316(6) 0.0364(8) 0.0228(5) -0.0012(6) 0.0011(5) 0.0035(6) C4 0.0330(9) 0.0467(12) 0.0265(8) 0.0008(9) 0.0038(7) 0.0109(9) C5 0.0339(10) 0.0623(16) 0.0323(9) -0.0016(11) -0.0004(8) 0.0043(10) C6 0.0574(13) 0.0424(12) 0.0362(10) 0.0074(10) 0.0051(9) 0.0049(11) C7 0.0484(12) 0.082(2) 0.0400(11) -0.0016(13) 0.0116(9) 0.0301(15) C8 0.0305(9) 0.0392(11) 0.0227(7) 0.0002(7) 0.0035(6) 0.0045(8) C9 0.0278(8) 0.0327(9) 0.0246(7) -0.0029(8) 0.0044(6) -0.0019(8) N10 0.0287(8) 0.0322(8) 0.0357(8) -0.0033(7) 0.0093(6) -0.0013(7) C11 0.0310(9) 0.0415(11) 0.0329(9) 0.0012(9) 0.0082(7) 0.0038(9) C12 0.0358(10) 0.0449(13) 0.0470(11) -0.0015(10) 0.0136(8) -0.0003(10) C13 0.0499(13) 0.0398(12) 0.0634(14) -0.0125(12) 0.0245(11) 0.0024(11) C14 0.0263(8) 0.0338(9) 0.0238(7) 0.0019(7) 0.0029(6) -0.0020(8) O15 0.0263(7) 0.0599(11) 0.0346(7) 0.0190(8) -0.0001(5) -0.0049(7) C16 0.0265(8) 0.0400(11) 0.0289(8) 0.0065(8) 0.0011(7) -0.0032(8) O17 0.0309(7) 0.0899(16) 0.0384(7) 0.0314(10) -0.0032(6) -0.0095(9) C18 0.0322(9) 0.0410(12) 0.0238(8) 0.0031(8) 0.0028(7) -0.0034(9) C19 0.0433(11) 0.0482(14) 0.0370(10) 0.0108(10) 0.0060(8) -0.0047(10) C20 0.0559(14) 0.0425(13) 0.0558(14) -0.0040(12) -0.0024(11) -0.0080(12) C21 0.0656(16) 0.0653(18) 0.0388(11) 0.0033(13) 0.0049(11) 0.0279(15) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.748(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.205(3) yes C2 . O3 . 1.352(2) yes C2 . C8 . 1.511(3) yes O3 . C4 . 1.484(3) yes C4 . C5 . 1.522(3) yes C4 . C6 . 1.518(4) yes C4 . C7 . 1.521(3) yes C5 . H51 . 1.002 no C5 . H52 . 0.954 no C5 . H53 . 0.952 no C6 . H61 . 0.979 no C6 . H62 . 0.987 no C6 . H63 . 0.938 no C7 . H71 . 0.981 no C7 . H72 . 0.977 no C7 . H73 . 0.969 no C8 . C9 . 1.550(2) yes C8 . H82 . 0.972 no C8 . H81 . 0.967 no C9 . N10 . 1.464(2) yes C9 . C14 . 1.526(3) yes C9 . H91 . 0.955 no N10 . C11 . 1.464(3) yes N10 . H101 . 0.889 no C11 . C12 . 1.527(3) yes C11 . C13 . 1.518(3) yes C11 . H111 . 0.986 no C12 . H121 . 0.978 no C12 . H122 . 0.955 no C12 . H123 . 0.950 no C13 . H133 . 0.980 no C13 . H132 . 0.954 no C13 . H131 . 0.923 no C14 . O15 . 1.429(2) yes C14 . C18 . 1.533(2) yes C14 . H141 . 1.007 no O15 . C16 . 1.439(2) yes C16 . O17 . 1.420(3) yes C16 . C20 . 1.501(3) yes C16 . C21 . 1.509(3) yes O17 . C18 . 1.432(3) yes C18 . C19 . 1.504(3) yes C18 . H181 . 0.976 no C19 . H191 . 0.926 no C19 . H192 . 0.964 no C19 . H193 . 0.962 no C20 . H202 . 0.960 no C20 . H201 . 0.961 no C20 . H203 . 0.960 no C21 . H212 . 0.974 no C21 . H211 . 0.946 no C21 . H213 . 0.946 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . C2 . O3 . 124.60(18) yes O1 . C2 . C8 . 124.40(17) yes O3 . C2 . C8 . 110.97(17) yes C2 . O3 . C4 . 121.21(16) yes O3 . C4 . C5 . 101.74(19) yes O3 . C4 . C6 . 109.40(17) yes C5 . C4 . C6 . 110.79(17) yes O3 . C4 . C7 . 110.83(17) yes C5 . C4 . C7 . 110.60(19) yes C6 . C4 . C7 . 112.9(2) yes C4 . C5 . H51 . 112.8 no C4 . C5 . H52 . 107.2 no H51 . C5 . H52 . 110.5 no C4 . C5 . H53 . 107.0 no H51 . C5 . H53 . 110.1 no H52 . C5 . H53 . 109.1 no C4 . C6 . H61 . 108.7 no C4 . C6 . H62 . 108.4 no H61 . C6 . H62 . 109.6 no C4 . C6 . H63 . 111.2 no H61 . C6 . H63 . 109.6 no H62 . C6 . H63 . 109.3 no C4 . C7 . H71 . 110.2 no C4 . C7 . H72 . 110.8 no H71 . C7 . H72 . 106.4 no C4 . C7 . H73 . 108.1 no H71 . C7 . H73 . 110.0 no H72 . C7 . H73 . 111.4 no C2 . C8 . C9 . 113.58(16) yes C2 . C8 . H82 . 112.5 no C9 . C8 . H82 . 105.6 no C2 . C8 . H81 . 105.3 no C9 . C8 . H81 . 112.1 no H82 . C8 . H81 . 107.7 no C8 . C9 . N10 . 114.76(15) yes C8 . C9 . C14 . 109.45(14) yes N10 . C9 . C14 . 107.90(16) yes C8 . C9 . H91 . 106.6 no N10 . C9 . H91 . 110.3 no C14 . C9 . H91 . 107.6 no C9 . N10 . C11 . 117.01(17) yes C9 . N10 . H101 . 107.2 no C11 . N10 . H101 . 103.4 no N10 . C11 . C12 . 108.09(19) yes N10 . C11 . C13 . 111.17(18) yes C12 . C11 . C13 . 110.12(18) yes N10 . C11 . H111 . 108.7 no C12 . C11 . H111 . 108.9 no C13 . C11 . H111 . 109.8 no C11 . C12 . H121 . 109.5 no C11 . C12 . H122 . 110.3 no H121 . C12 . H122 . 107.9 no C11 . C12 . H123 . 112.1 no H121 . C12 . H123 . 106.8 no H122 . C12 . H123 . 110.2 no C11 . C13 . H133 . 107.5 no C11 . C13 . H132 . 116.5 no H133 . C13 . H132 . 110.9 no C11 . C13 . H131 . 104.2 no H133 . C13 . H131 . 110.2 no H132 . C13 . H131 . 107.3 no C9 . C14 . O15 . 107.89(16) yes C9 . C14 . C18 . 115.41(16) yes O15 . C14 . C18 . 102.77(14) yes C9 . C14 . H141 . 108.2 no O15 . C14 . H141 . 112.7 no C18 . C14 . H141 . 109.8 no C14 . O15 . C16 . 108.41(15) yes O15 . C16 . O17 . 106.45(15) yes O15 . C16 . C20 . 108.1(2) yes O17 . C16 . C20 . 111.77(19) yes O15 . C16 . C21 . 110.14(17) yes O17 . C16 . C21 . 108.0(2) yes C20 . C16 . C21 . 112.2(2) yes C16 . O17 . C18 . 109.52(15) yes C14 . C18 . O17 . 102.53(15) yes C14 . C18 . C19 . 115.89(18) yes O17 . C18 . C19 . 107.34(19) yes C14 . C18 . H181 . 111.4 no O17 . C18 . H181 . 108.1 no C19 . C18 . H181 . 110.9 no C18 . C19 . H191 . 107.8 no C18 . C19 . H192 . 109.0 no H191 . C19 . H192 . 109.1 no C18 . C19 . H193 . 109.8 no H191 . C19 . H193 . 110.6 no H192 . C19 . H193 . 110.5 no C16 . C20 . H202 . 108.2 no C16 . C20 . H201 . 108.8 no H202 . C20 . H201 . 111.9 no C16 . C20 . H203 . 108.4 no H202 . C20 . H203 . 110.9 no H201 . C20 . H203 . 108.5 no C16 . C21 . H212 . 107.6 no C16 . C21 . H211 . 110.6 no H212 . C21 . H211 . 110.4 no C16 . C21 . H213 . 107.6 no H212 . C21 . H213 . 109.5 no H211 . C21 . H213 . 111.0 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N10 . H101 . O1 1_565 156 0.89 2.40 3.229(3) yes #============================================================================== data_67 _database_code_depnum_ccdc_archive 'CCDC 846622' #TrackingRef 'CrystallographicData.cif' _ccdc_journal_depnumber ? #============================================================================== _cell_length_a 5.7565(2) _cell_length_b 19.4300(8) _cell_length_c 8.1386(3) _cell_angle_alpha 90 _cell_angle_beta 96.168(2) _cell_angle_gamma 90 _cell_volume 905.02(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C16 H31 N1 O4 # Dc = 1.11 Fooo = 332.00 Mu = 0.78 M = 301.43 # Found Formula = C16 H31 N1 O4 # Dc = 1.11 FOOO = 332.00 Mu = 0.78 M = 301.43 _chemical_formula_sum 'C16 H31 N1 O4' _chemical_formula_moiety 'C16 H31 N1 O4' _chemical_compound_source . _chemical_formula_weight 301.43 _cell_measurement_reflns_used 2044 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.070 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_max 0.260 _exptl_crystal_density_diffrn 1.106 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.078 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 3857 _reflns_number_total 2122 _diffrn_reflns_av_R_equivalents 0.024 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 2122 # Theoretical number of reflections is about 3736 _diffrn_reflns_theta_min 5.148 _diffrn_reflns_theta_max 27.509 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.308 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 25 _reflns_limit_l_min 0 _reflns_limit_l_max 10 _oxford_diffrn_Wilson_B_factor 3.13 _oxford_diffrn_Wilson_scale 0.77 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.17 _refine_diff_density_max 0.20 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 1907 _refine_ls_number_restraints 1 _refine_ls_number_parameters 190 _oxford_refine_ls_R_factor_ref 0.0433 _refine_ls_wR_factor_ref 0.0936 _refine_ls_goodness_of_fit_ref 0.9192 _refine_ls_shift/su_max 0.0002656 _refine_ls_shift/su_mean 0.0000272 # The values computed from all data _oxford_reflns_number_all 1907 _refine_ls_R_factor_all 0.0433 _refine_ls_wR_factor_all 0.0936 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1693 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_gt 0.0839 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration (3R,4R,5S) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 29.8 49.0 30.1 13.2 3.35 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.7573(3) 0.65136(10) 0.70241(19) 0.0307 1.0000 Uani . . . . . . C2 C 0.7088(4) 0.71880(13) 0.7075(2) 0.0262 1.0000 Uani . . . . . . O3 O 0.5132(3) 0.74277(11) 0.69660(19) 0.0329 1.0000 Uani . . . . . . C4 C 0.9287(4) 0.76061(12) 0.7388(3) 0.0290 1.0000 Uani . . . . . . C5 C 0.9479(4) 0.82060(13) 0.6169(3) 0.0266 1.0000 Uani . . . . . . N6 N 1.1468(3) 0.86592(12) 0.6668(2) 0.0302 1.0000 Uani . . . . . . C7 C 1.1292(5) 0.90717(14) 0.8153(3) 0.0387 1.0000 Uani . . . . . . C8 C 0.9816(6) 0.97070(16) 0.7736(4) 0.0543 1.0000 Uani . . . . . . C9 C 1.3729(7) 0.92818(19) 0.8853(5) 0.0680 1.0000 Uani . . . . . . C10 C 0.9815(4) 0.79310(13) 0.4464(3) 0.0275 1.0000 Uani . . . . . . O11 O 0.7898(3) 0.74874(10) 0.39148(17) 0.0321 1.0000 Uani . . . . . . C12 C 0.7858(4) 0.74183(14) 0.2159(3) 0.0304 1.0000 Uani . . . . . . O13 O 0.9145(3) 0.79991(11) 0.16376(19) 0.0355 1.0000 Uani . . . . . . C14 C 0.9779(4) 0.84387(13) 0.3031(3) 0.0311 1.0000 Uani . . . . . . C15 C 0.8074(5) 0.90271(14) 0.3080(3) 0.0389 1.0000 Uani . . . . . . C16 C 0.9079(5) 0.67673(14) 0.1731(3) 0.0360 1.0000 Uani . . . . . . C17 C 0.5344(4) 0.74502(17) 0.1413(3) 0.0410 1.0000 Uani . . . . . . C18 C 0.5717(4) 0.59859(14) 0.6759(3) 0.0334 1.0000 Uani . . . . . . C19 C 0.4279(5) 0.59731(15) 0.8217(3) 0.0399 1.0000 Uani . . . . . . C20 C 0.7154(5) 0.53333(14) 0.6704(4) 0.0488 1.0000 Uani . . . . . . C21 C 0.4223(5) 0.61077(16) 0.5136(4) 0.0489 1.0000 Uani . . . . . . H41 H 1.0641 0.7308 0.7396 0.0349 1.0000 Uiso R . . . . . H42 H 0.9286 0.7802 0.8480 0.0341 1.0000 Uiso R . . . . . H51 H 0.7999 0.8476 0.6086 0.0317 1.0000 Uiso R . . . . . H71 H 1.0586 0.8799 0.8997 0.0451 1.0000 Uiso R . . . . . H83 H 0.9576 0.9946 0.8736 0.0809 1.0000 Uiso R . . . . . H82 H 0.8338 0.9569 0.7144 0.0813 1.0000 Uiso R . . . . . H81 H 1.0658 0.9993 0.7034 0.0819 1.0000 Uiso R . . . . . H91 H 1.3679 0.9541 0.9825 0.0962 1.0000 Uiso R . . . . . H93 H 1.4688 0.8880 0.9082 0.0963 1.0000 Uiso R . . . . . H92 H 1.4372 0.9577 0.8029 0.0956 1.0000 Uiso R . . . . . H101 H 1.1308 0.7671 0.4581 0.0335 1.0000 Uiso R . . . . . H141 H 1.1379 0.8609 0.2989 0.0357 1.0000 Uiso R . . . . . H152 H 0.7969 0.9274 0.2060 0.0549 1.0000 Uiso R . . . . . H151 H 0.6555 0.8860 0.3254 0.0557 1.0000 Uiso R . . . . . H153 H 0.8590 0.9344 0.3957 0.0546 1.0000 Uiso R . . . . . H161 H 0.9256 0.6763 0.0570 0.0536 1.0000 Uiso R . . . . . H163 H 0.8239 0.6375 0.2013 0.0532 1.0000 Uiso R . . . . . H162 H 1.0610 0.6752 0.2354 0.0530 1.0000 Uiso R . . . . . H171 H 0.5291 0.7455 0.0208 0.0593 1.0000 Uiso R . . . . . H173 H 0.4540 0.7045 0.1754 0.0595 1.0000 Uiso R . . . . . H172 H 0.4638 0.7865 0.1790 0.0586 1.0000 Uiso R . . . . . H191 H 0.3127 0.5612 0.8048 0.0579 1.0000 Uiso R . . . . . H192 H 0.5258 0.5889 0.9236 0.0575 1.0000 Uiso R . . . . . H193 H 0.3483 0.6403 0.8323 0.0576 1.0000 Uiso R . . . . . H202 H 0.6189 0.4950 0.6479 0.0750 1.0000 Uiso R . . . . . H201 H 0.8080 0.5262 0.7751 0.0748 1.0000 Uiso R . . . . . H203 H 0.8226 0.5371 0.5881 0.0752 1.0000 Uiso R . . . . . H212 H 0.3077 0.5754 0.4941 0.0751 1.0000 Uiso R . . . . . H211 H 0.5156 0.6112 0.4251 0.0746 1.0000 Uiso R . . . . . H213 H 0.3413 0.6543 0.5154 0.0752 1.0000 Uiso R . . . . . H61 H 1.2815 0.8453 0.6683 0.0357 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0312(8) 0.0230(7) 0.0378(8) -0.0004(6) 0.0027(6) -0.0021(6) C2 0.0310(11) 0.0259(10) 0.0217(9) 0.0019(8) 0.0029(8) -0.0006(9) O3 0.0295(8) 0.0314(8) 0.0382(8) 0.0004(7) 0.0054(6) 0.0014(7) C4 0.0336(11) 0.0261(11) 0.0269(10) 0.0014(8) 0.0011(8) -0.0015(8) C5 0.0282(10) 0.0265(10) 0.0252(10) -0.0002(8) 0.0035(8) -0.0022(8) N6 0.0299(10) 0.0285(9) 0.0322(10) -0.0029(8) 0.0038(7) -0.0031(8) C7 0.0511(14) 0.0316(12) 0.0338(12) -0.0049(10) 0.0056(10) -0.0075(11) C8 0.0639(18) 0.0406(15) 0.0598(17) -0.0166(13) 0.0126(14) 0.0018(14) C9 0.068(2) 0.058(2) 0.071(2) -0.0273(17) -0.0205(16) -0.0005(17) C10 0.0289(10) 0.0260(10) 0.0275(10) -0.0001(8) 0.0021(8) -0.0016(8) O11 0.0407(8) 0.0335(8) 0.0223(7) -0.0028(6) 0.0038(6) -0.0116(7) C12 0.0368(10) 0.0320(11) 0.0226(9) 0.0010(9) 0.0040(8) -0.0057(10) O13 0.0474(10) 0.0351(9) 0.0245(8) 0.0012(7) 0.0064(6) -0.0065(8) C14 0.0353(11) 0.0316(11) 0.0268(11) 0.0009(9) 0.0049(9) -0.0037(9) C15 0.0511(14) 0.0302(12) 0.0347(12) 0.0067(10) 0.0014(10) 0.0052(11) C16 0.0419(13) 0.0355(12) 0.0303(11) -0.0037(10) 0.0029(9) 0.0007(10) C17 0.0344(12) 0.0543(15) 0.0336(11) -0.0070(12) 0.0009(9) -0.0006(12) C18 0.0352(11) 0.0259(11) 0.0389(12) -0.0007(9) 0.0037(9) -0.0054(9) C19 0.0399(13) 0.0364(13) 0.0440(13) 0.0035(11) 0.0080(10) -0.0078(11) C20 0.0548(16) 0.0261(12) 0.0670(18) -0.0046(12) 0.0132(13) -0.0025(12) C21 0.0586(17) 0.0449(16) 0.0403(13) -0.0013(12) -0.0087(12) -0.0136(13) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.069(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.341(3) yes O1 . C18 . 1.480(3) yes C2 . O3 . 1.213(3) yes C2 . C4 . 1.502(3) yes C4 . C5 . 1.542(3) yes C4 . H41 . 0.970 no C4 . H42 . 0.967 no C5 . N6 . 1.467(3) yes C5 . C10 . 1.518(3) yes C5 . H51 . 0.996 no N6 . C7 . 1.462(3) yes N6 . H61 . 0.872 no C7 . C8 . 1.516(4) yes C7 . C9 . 1.513(4) yes C7 . H71 . 0.988 no C8 . H83 . 0.961 no C8 . H82 . 0.969 no C8 . H81 . 0.964 no C9 . H91 . 0.941 no C9 . H93 . 0.962 no C9 . H92 . 0.984 no C10 . O11 . 1.433(3) yes C10 . C14 . 1.526(3) yes C10 . H101 . 0.993 no O11 . C12 . 1.433(2) yes C12 . O13 . 1.439(3) yes C12 . C16 . 1.506(3) yes C12 . C17 . 1.509(3) yes O13 . C14 . 1.435(3) yes C14 . C15 . 1.510(3) yes C14 . H141 . 0.983 no C15 . H152 . 0.955 no C15 . H151 . 0.958 no C15 . H153 . 0.965 no C16 . H161 . 0.962 no C16 . H163 . 0.944 no C16 . H162 . 0.969 no C17 . H171 . 0.978 no C17 . H173 . 0.970 no C17 . H172 . 0.967 no C18 . C19 . 1.518(4) yes C18 . C20 . 1.517(4) yes C18 . C21 . 1.515(4) yes C19 . H191 . 0.965 no C19 . H192 . 0.965 no C19 . H193 . 0.961 no C20 . H202 . 0.935 no C20 . H201 . 0.965 no C20 . H203 . 0.961 no C21 . H212 . 0.954 no C21 . H211 . 0.944 no C21 . H213 . 0.966 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C18 . 122.13(18) yes O1 . C2 . O3 . 124.6(2) yes O1 . C2 . C4 . 111.04(18) yes O3 . C2 . C4 . 124.3(2) yes C2 . C4 . C5 . 114.61(17) yes C2 . C4 . H41 . 109.9 no C5 . C4 . H41 . 110.0 no C2 . C4 . H42 . 106.6 no C5 . C4 . H42 . 107.5 no H41 . C4 . H42 . 108.0 no C4 . C5 . N6 . 112.54(17) yes C4 . C5 . C10 . 110.30(18) yes N6 . C5 . C10 . 106.98(17) yes C4 . C5 . H51 . 108.8 no N6 . C5 . H51 . 109.8 no C10 . C5 . H51 . 108.3 no C5 . N6 . C7 . 115.89(18) yes C5 . N6 . H61 . 113.2 no C7 . N6 . H61 . 112.4 no N6 . C7 . C8 . 110.4(2) yes N6 . C7 . C9 . 108.4(2) yes C8 . C7 . C9 . 109.8(2) yes N6 . C7 . H71 . 110.5 no C8 . C7 . H71 . 109.2 no C9 . C7 . H71 . 108.4 no C7 . C8 . H83 . 109.4 no C7 . C8 . H82 . 109.1 no H83 . C8 . H82 . 110.9 no C7 . C8 . H81 . 107.2 no H83 . C8 . H81 . 110.5 no H82 . C8 . H81 . 109.6 no C7 . C9 . H91 . 110.5 no C7 . C9 . H93 . 110.1 no H91 . C9 . H93 . 109.9 no C7 . C9 . H92 . 107.6 no H91 . C9 . H92 . 108.0 no H93 . C9 . H92 . 110.7 no C5 . C10 . O11 . 109.11(16) yes C5 . C10 . C14 . 118.58(19) yes O11 . C10 . C14 . 101.73(16) yes C5 . C10 . H101 . 106.6 no O11 . C10 . H101 . 110.7 no C14 . C10 . H101 . 110.0 no C10 . O11 . C12 . 107.28(15) yes O11 . C12 . O13 . 105.48(17) yes O11 . C12 . C16 . 110.57(18) yes O13 . C12 . C16 . 108.82(17) yes O11 . C12 . C17 . 108.04(17) yes O13 . C12 . C17 . 110.6(2) yes C16 . C12 . C17 . 113.1(2) yes C12 . O13 . C14 . 109.19(16) yes C10 . C14 . O13 . 101.58(18) yes C10 . C14 . C15 . 115.14(19) yes O13 . C14 . C15 . 111.15(19) yes C10 . C14 . H141 . 108.0 no O13 . C14 . H141 . 109.4 no C15 . C14 . H141 . 111.1 no C14 . C15 . H152 . 109.8 no C14 . C15 . H151 . 110.7 no H152 . C15 . H151 . 109.0 no C14 . C15 . H153 . 110.7 no H152 . C15 . H153 . 107.9 no H151 . C15 . H153 . 108.7 no C12 . C16 . H161 . 109.6 no C12 . C16 . H163 . 111.0 no H161 . C16 . H163 . 110.1 no C12 . C16 . H162 . 109.0 no H161 . C16 . H162 . 109.1 no H163 . C16 . H162 . 108.1 no C12 . C17 . H171 . 109.2 no C12 . C17 . H173 . 108.5 no H171 . C17 . H173 . 109.3 no C12 . C17 . H172 . 108.9 no H171 . C17 . H172 . 110.0 no H173 . C17 . H172 . 110.8 no O1 . C18 . C19 . 110.07(19) yes O1 . C18 . C20 . 101.30(19) yes C19 . C18 . C20 . 110.8(2) yes O1 . C18 . C21 . 110.62(19) yes C19 . C18 . C21 . 112.2(2) yes C20 . C18 . C21 . 111.4(2) yes C18 . C19 . H191 . 108.9 no C18 . C19 . H192 . 110.9 no H191 . C19 . H192 . 109.2 no C18 . C19 . H193 . 111.2 no H191 . C19 . H193 . 108.5 no H192 . C19 . H193 . 108.1 no C18 . C20 . H202 . 110.9 no C18 . C20 . H201 . 110.2 no H202 . C20 . H201 . 108.5 no C18 . C20 . H203 . 110.5 no H202 . C20 . H203 . 109.6 no H201 . C20 . H203 . 107.0 no C18 . C21 . H212 . 110.5 no C18 . C21 . H211 . 110.5 no H212 . C21 . H211 . 108.6 no C18 . C21 . H213 . 110.7 no H212 . C21 . H213 . 107.9 no H211 . C21 . H213 . 108.6 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N6 . H61 . O3 1_655 150 0.87 2.39 3.182(4) yes #============================================================================== data_68 _database_code_depnum_ccdc_archive 'CCDC 846623' #TrackingRef 'CrystallographicData.cif' _ccdc_journal_depnumber ? #============================================================================== _cell_length_a 7.9717(2) _cell_length_b 12.5518(3) _cell_length_c 13.0678(3) _cell_angle_alpha 90 _cell_angle_beta 95.5854(9) _cell_angle_gamma 90 _cell_volume 1301.35(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C28 H39 N1 O4 # Dc = 1.16 Fooo = 492.00 Mu = 0.76 M = 453.62 # Found Formula = C28 H39 N1 O4 # Dc = 1.16 FOOO = 492.00 Mu = 0.76 M = 453.62 _chemical_formula_sum 'C28 H39 N1 O4' _chemical_formula_moiety 'C28 H39 N1 O4' _chemical_compound_source . _chemical_formula_weight 453.62 _cell_measurement_reflns_used 3043 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.180 _exptl_crystal_size_mid 0.230 _exptl_crystal_size_max 0.270 _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 0.076 # Sheldrick geometric approximatio 0.98 0.99 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 5876 _reflns_number_total 3107 _diffrn_reflns_av_R_equivalents 0.020 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 3107 # Theoretical number of reflections is about 4906 _diffrn_reflns_theta_min 5.119 _diffrn_reflns_theta_max 27.553 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.002 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _oxford_diffrn_Wilson_B_factor 2.74 _oxford_diffrn_Wilson_scale 1.24 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.19 _refine_diff_density_max 0.26 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 2549 _refine_ls_number_restraints 1 _refine_ls_number_parameters 298 _oxford_refine_ls_R_factor_ref 0.0457 _refine_ls_wR_factor_ref 0.1173 _refine_ls_goodness_of_fit_ref 0.9837 _refine_ls_shift/su_max 0.0002039 _refine_ls_shift/su_mean 0.0000195 # The values computed from all data _oxford_reflns_number_all 2549 _refine_ls_R_factor_all 0.0457 _refine_ls_wR_factor_all 0.1173 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2422 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_gt 0.1153 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration (3R,4R,5S,\aR) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 31.2 50.4 29.9 12.4 3.13 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O 0.5026(2) 0.65327(18) 0.92745(14) 0.0284 1.0000 Uani . . . . . . . C2 C 0.6705(4) 0.6640(3) 0.9398(2) 0.0282 1.0000 Uani . . . . . . . O3 O 0.7479(3) 0.7142(2) 1.00758(18) 0.0420 1.0000 Uani . . . . . . . C4 C 0.7522(3) 0.5989(2) 0.8613(2) 0.0253 1.0000 Uani . . . . . . . C5 C 0.6829(3) 0.6205(2) 0.7494(2) 0.0232 1.0000 Uani . . . . . . . N6 N 0.7295(3) 0.7292(2) 0.72070(19) 0.0246 1.0000 Uani . . . . . . . C7 C 0.9012(4) 0.7428(2) 0.6929(2) 0.0267 1.0000 Uani . . . . . . . C8 C 0.9675(4) 0.8538(2) 0.7204(2) 0.0279 1.0000 Uani . . . . . . . C9 C 1.0334(4) 0.9180(3) 0.6479(3) 0.0334 1.0000 Uani . . . . . . . C10 C 1.0984(4) 1.0185(3) 0.6750(3) 0.0407 1.0000 Uani . . . . . . . C11 C 1.0991(4) 1.0542(3) 0.7745(3) 0.0424 1.0000 Uani . . . . . . . C12 C 1.0323(5) 0.9911(3) 0.8473(3) 0.0434 1.0000 Uani . . . . . . . C13 C 0.9663(4) 0.8917(3) 0.8196(3) 0.0369 1.0000 Uani . . . . . . . C14 C 0.6011(4) 0.7917(2) 0.6561(2) 0.0289 1.0000 Uani . . . . . . . C15 C 0.5057(4) 0.7274(2) 0.5695(2) 0.0284 1.0000 Uani . . . . . . . C16 C 0.3521(4) 0.6795(3) 0.5804(2) 0.0335 1.0000 Uani . . . . . . . C17 C 0.2705(4) 0.6168(3) 0.5027(3) 0.0416 1.0000 Uani . . . . . . . C18 C 0.3435(5) 0.6008(3) 0.4122(3) 0.0427 1.0000 Uani . . . . . . . C19 C 0.4967(5) 0.6491(3) 0.3993(3) 0.0418 1.0000 Uani . . . . . . . C20 C 0.5750(4) 0.7120(3) 0.4774(2) 0.0337 1.0000 Uani . . . . . . . C21 C 0.4856(4) 0.8475(3) 0.7246(3) 0.0396 1.0000 Uani . . . . . . . C22 C 0.7341(3) 0.5314(2) 0.6777(2) 0.0236 1.0000 Uani . . . . . . . O23 O 0.9086(2) 0.50297(17) 0.70154(16) 0.0275 1.0000 Uani . . . . . . . C24 C 0.9218(4) 0.3929(2) 0.7318(2) 0.0271 1.0000 Uani . . . . . . . O25 O 0.7560(2) 0.36374(17) 0.75443(15) 0.0266 1.0000 Uani . . . . . . . C26 C 0.6423(4) 0.4237(2) 0.6849(2) 0.0258 1.0000 Uani . . . . . . . C27 C 0.4693(4) 0.4237(3) 0.7239(3) 0.0331 1.0000 Uani . . . . . . . C28 C 1.0392(4) 0.3814(3) 0.8289(2) 0.0360 1.0000 Uani . . . . . . . C29 C 0.9766(4) 0.3274(3) 0.6440(3) 0.0347 1.0000 Uani . . . . . . . C30 C 0.3936(4) 0.6994(3) 1.0024(2) 0.0330 1.0000 Uani . . . . . . . C31 C 0.4075(5) 0.8191(3) 1.0050(3) 0.0449 1.0000 Uani . . . . . . . C32 C 0.2191(4) 0.6649(4) 0.9560(3) 0.0483 1.0000 Uani . . . . . . . C33 C 0.4370(5) 0.6487(4) 1.1068(3) 0.0487 1.0000 Uani . . . . . . . H41 H 0.7373 0.5240 0.8749 0.0270 1.0000 Uiso R . . . . . . H42 H 0.8757 0.6125 0.8697 0.0277 1.0000 Uiso R . . . . . . H51 H 0.5594 0.6192 0.7449 0.0282 1.0000 Uiso R . . . . . . H71 H 0.9034 0.7333 0.6183 0.0306 1.0000 Uiso R . . . . . . H72 H 0.9706 0.6901 0.7315 0.0306 1.0000 Uiso R . . . . . . H91 H 1.0324 0.8933 0.5805 0.0388 1.0000 Uiso R . . . . . . H101 H 1.1414 1.0618 0.6272 0.0500 1.0000 Uiso R . . . . . . H111 H 1.1428 1.1210 0.7962 0.0458 1.0000 Uiso R . . . . . . H121 H 1.0308 1.0139 0.9168 0.0480 1.0000 Uiso R . . . . . . H131 H 0.9172 0.8514 0.8709 0.0421 1.0000 Uiso R . . . . . . H141 H 0.6638 0.8476 0.6223 0.0318 1.0000 Uiso R . . . . . . H161 H 0.3041 0.6901 0.6425 0.0377 1.0000 Uiso R . . . . . . H171 H 0.1664 0.5863 0.5124 0.0428 1.0000 Uiso R . . . . . . H181 H 0.2902 0.5572 0.3601 0.0509 1.0000 Uiso R . . . . . . H191 H 0.5472 0.6410 0.3381 0.0471 1.0000 Uiso R . . . . . . H201 H 0.6765 0.7447 0.4679 0.0389 1.0000 Uiso R . . . . . . H211 H 0.4032 0.8892 0.6821 0.0571 1.0000 Uiso R . . . . . . H212 H 0.4278 0.7943 0.7618 0.0574 1.0000 Uiso R . . . . . . H213 H 0.5515 0.8930 0.7738 0.0568 1.0000 Uiso R . . . . . . H221 H 0.7220 0.5574 0.6056 0.0250 1.0000 Uiso R . . . . . . H261 H 0.6305 0.3895 0.6161 0.0288 1.0000 Uiso R . . . . . . H273 H 0.4294 0.3513 0.7327 0.0481 1.0000 Uiso R . . . . . . H272 H 0.3897 0.4597 0.6743 0.0480 1.0000 Uiso R . . . . . . H271 H 0.4746 0.4587 0.7895 0.0481 1.0000 Uiso R . . . . . . H281 H 1.0644 0.3074 0.8382 0.0530 1.0000 Uiso R . . . . . . H282 H 1.1422 0.4184 0.8222 0.0526 1.0000 Uiso R . . . . . . H283 H 0.9858 0.4091 0.8878 0.0540 1.0000 Uiso R . . . . . . H291 H 0.9883 0.2541 0.6619 0.0489 1.0000 Uiso R . . . . . . H292 H 0.8938 0.3340 0.5852 0.0495 1.0000 Uiso R . . . . . . H293 H 1.0828 0.3549 0.6284 0.0492 1.0000 Uiso R . . . . . . H313 H 0.3199 0.8467 1.0434 0.0625 1.0000 Uiso R . . . . . . H312 H 0.3944 0.8463 0.9345 0.0631 1.0000 Uiso R . . . . . . H311 H 0.5142 0.8389 1.0399 0.0630 1.0000 Uiso R . . . . . . H321 H 0.1342 0.7005 0.9909 0.0706 1.0000 Uiso R . . . . . . H322 H 0.2059 0.5886 0.9640 0.0716 1.0000 Uiso R . . . . . . H323 H 0.2056 0.6818 0.8830 0.0712 1.0000 Uiso R . . . . . . H331 H 0.3589 0.6733 1.1549 0.0700 1.0000 Uiso R . . . . . . H332 H 0.4286 0.5727 1.0978 0.0698 1.0000 Uiso R . . . . . . H333 H 0.5491 0.6668 1.1314 0.0701 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0235(10) 0.0357(12) 0.0262(10) -0.0082(9) 0.0036(8) 0.0022(9) C2 0.0274(14) 0.0325(16) 0.0241(13) -0.0027(13) -0.0009(11) -0.0001(13) O3 0.0332(12) 0.0557(16) 0.0358(12) -0.0206(11) -0.0029(9) -0.0038(11) C4 0.0236(13) 0.0274(15) 0.0245(13) 0.0010(11) 0.0010(11) 0.0042(11) C5 0.0216(13) 0.0206(13) 0.0268(13) 0.0001(11) -0.0015(10) -0.0007(11) N6 0.0211(11) 0.0213(12) 0.0305(12) 0.0026(10) -0.0024(9) 0.0018(10) C7 0.0244(14) 0.0248(15) 0.0310(15) -0.0025(12) 0.0031(11) -0.0002(11) C8 0.0227(13) 0.0237(14) 0.0368(15) -0.0005(12) -0.0007(11) 0.0031(12) C9 0.0291(15) 0.0308(16) 0.0404(17) -0.0004(14) 0.0036(12) 0.0014(13) C10 0.0310(17) 0.0299(17) 0.061(2) 0.0085(17) 0.0032(15) -0.0037(14) C11 0.0314(16) 0.0250(16) 0.068(2) -0.0025(16) -0.0114(16) -0.0016(14) C12 0.049(2) 0.0345(19) 0.0444(19) -0.0087(16) -0.0089(16) -0.0036(16) C13 0.0390(17) 0.0330(17) 0.0372(17) -0.0016(14) -0.0029(13) -0.0038(14) C14 0.0292(15) 0.0237(14) 0.0323(15) 0.0031(12) -0.0041(12) 0.0055(12) C15 0.0280(14) 0.0236(15) 0.0320(15) 0.0043(12) -0.0048(11) 0.0050(12) C16 0.0300(15) 0.0377(17) 0.0322(15) 0.0032(13) -0.0005(12) 0.0025(13) C17 0.0339(16) 0.0407(19) 0.0467(19) 0.0028(16) -0.0138(14) -0.0031(15) C18 0.050(2) 0.0363(19) 0.0377(18) -0.0059(15) -0.0152(15) 0.0058(16) C19 0.0481(19) 0.048(2) 0.0282(15) -0.0023(15) -0.0048(13) 0.0142(17) C20 0.0351(16) 0.0346(18) 0.0306(15) 0.0067(14) -0.0016(12) 0.0048(14) C21 0.0384(18) 0.0359(18) 0.0427(18) -0.0065(15) -0.0055(14) 0.0137(15) C22 0.0246(13) 0.0225(14) 0.0233(13) 0.0015(11) 0.0005(10) 0.0024(11) O23 0.0237(10) 0.0216(10) 0.0375(11) 0.0015(9) 0.0044(8) 0.0031(8) C24 0.0270(14) 0.0222(14) 0.0320(15) 0.0018(12) 0.0023(11) 0.0036(11) O25 0.0259(10) 0.0251(11) 0.0288(10) 0.0062(8) 0.0029(8) 0.0024(8) C26 0.0268(14) 0.0231(14) 0.0268(13) -0.0004(12) -0.0016(10) 0.0003(12) C27 0.0259(14) 0.0316(16) 0.0410(17) 0.0026(14) -0.0010(12) -0.0028(13) C28 0.0330(16) 0.0410(18) 0.0336(16) 0.0008(15) 0.0010(12) 0.0100(14) C29 0.0411(18) 0.0266(15) 0.0372(16) -0.0031(13) 0.0085(14) 0.0048(13) C30 0.0309(16) 0.0425(19) 0.0261(14) -0.0066(13) 0.0056(12) 0.0070(13) C31 0.054(2) 0.043(2) 0.0389(18) -0.0080(16) 0.0105(16) 0.0098(17) C32 0.0287(16) 0.066(3) 0.051(2) -0.015(2) 0.0105(14) 0.0019(17) C33 0.052(2) 0.061(3) 0.0347(17) 0.0048(18) 0.0102(15) 0.013(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.877(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.339(4) yes O1 . C30 . 1.488(3) yes C2 . O3 . 1.207(4) yes C2 . C4 . 1.508(4) yes C4 . C5 . 1.536(4) yes C4 . H41 . 0.966 no C4 . H42 . 0.994 no C5 . N6 . 1.473(4) yes C5 . C22 . 1.540(4) yes C5 . H51 . 0.981 no N6 . C7 . 1.460(4) yes N6 . C14 . 1.486(4) yes C7 . C8 . 1.520(4) yes C7 . H71 . 0.984 no C7 . H72 . 0.972 no C8 . C9 . 1.385(5) yes C8 . C13 . 1.383(5) yes C9 . C10 . 1.397(5) yes C9 . H91 . 0.934 no C10 . C11 . 1.375(6) yes C10 . H101 . 0.918 no C11 . C12 . 1.384(5) yes C11 . H111 . 0.941 no C12 . C13 . 1.388(5) yes C12 . H121 . 0.954 no C13 . H131 . 0.953 no C14 . C15 . 1.531(4) yes C14 . C21 . 1.517(5) yes C14 . H141 . 0.990 no C15 . C16 . 1.384(4) yes C15 . C20 . 1.386(4) yes C16 . C17 . 1.395(5) yes C16 . H161 . 0.940 no C17 . C18 . 1.383(5) yes C17 . H171 . 0.934 no C18 . C19 . 1.388(6) yes C18 . H181 . 0.942 no C19 . C20 . 1.389(5) yes C19 . H191 . 0.936 no C20 . H201 . 0.926 no C21 . H211 . 0.971 no C21 . H212 . 0.968 no C21 . H213 . 0.974 no C22 . O23 . 1.441(3) yes C22 . C26 . 1.544(4) yes C22 . H221 . 0.993 no O23 . C24 . 1.439(4) yes C24 . O25 . 1.429(4) yes C24 . C28 . 1.508(4) yes C24 . C29 . 1.511(4) yes O25 . C26 . 1.433(3) yes C26 . C27 . 1.516(4) yes C26 . H261 . 0.993 no C27 . H273 . 0.973 no C27 . H272 . 0.973 no C27 . H271 . 0.961 no C28 . H281 . 0.955 no C28 . H282 . 0.955 no C28 . H283 . 0.979 no C29 . H291 . 0.951 no C29 . H292 . 0.966 no C29 . H293 . 0.955 no C30 . C31 . 1.506(5) yes C30 . C32 . 1.525(5) yes C30 . C33 . 1.515(5) yes C31 . H313 . 0.964 no C31 . H312 . 0.978 no C31 . H311 . 0.958 no C32 . H321 . 0.961 no C32 . H322 . 0.970 no C32 . H323 . 0.973 no C33 . H331 . 0.977 no C33 . H332 . 0.963 no C33 . H333 . 0.948 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C30 . 121.5(2) yes O1 . C2 . O3 . 125.0(3) yes O1 . C2 . C4 . 110.9(2) yes O3 . C2 . C4 . 123.9(3) yes C2 . C4 . C5 . 114.4(2) yes C2 . C4 . H41 . 109.4 no C5 . C4 . H41 . 107.9 no C2 . C4 . H42 . 108.7 no C5 . C4 . H42 . 109.6 no H41 . C4 . H42 . 106.6 no C4 . C5 . N6 . 109.3(2) yes C4 . C5 . C22 . 111.1(2) yes N6 . C5 . C22 . 115.5(2) yes C4 . C5 . H51 . 108.7 no N6 . C5 . H51 . 106.0 no C22 . C5 . H51 . 106.0 no C5 . N6 . C7 . 115.9(2) yes C5 . N6 . C14 . 117.2(2) yes C7 . N6 . C14 . 114.1(2) yes N6 . C7 . C8 . 111.2(2) yes N6 . C7 . H71 . 109.9 no C8 . C7 . H71 . 107.8 no N6 . C7 . H72 . 107.0 no C8 . C7 . H72 . 109.5 no H71 . C7 . H72 . 111.5 no C7 . C8 . C9 . 121.2(3) yes C7 . C8 . C13 . 120.2(3) yes C9 . C8 . C13 . 118.6(3) yes C8 . C9 . C10 . 120.6(3) yes C8 . C9 . H91 . 118.9 no C10 . C9 . H91 . 120.5 no C9 . C10 . C11 . 120.1(3) yes C9 . C10 . H101 . 121.1 no C11 . C10 . H101 . 118.9 no C10 . C11 . C12 . 119.8(3) yes C10 . C11 . H111 . 122.8 no C12 . C11 . H111 . 117.3 no C11 . C12 . C13 . 119.8(3) yes C11 . C12 . H121 . 121.6 no C13 . C12 . H121 . 118.6 no C12 . C13 . C8 . 121.1(3) yes C12 . C13 . H131 . 117.7 no C8 . C13 . H131 . 121.2 no N6 . C14 . C15 . 114.0(2) yes N6 . C14 . C21 . 109.4(2) yes C15 . C14 . C21 . 113.2(3) yes N6 . C14 . H141 . 106.2 no C15 . C14 . H141 . 106.2 no C21 . C14 . H141 . 107.4 no C14 . C15 . C16 . 122.2(3) yes C14 . C15 . C20 . 120.3(3) yes C16 . C15 . C20 . 117.4(3) yes C15 . C16 . C17 . 121.6(3) yes C15 . C16 . H161 . 117.8 no C17 . C16 . H161 . 120.6 no C16 . C17 . C18 . 119.9(3) yes C16 . C17 . H171 . 119.4 no C18 . C17 . H171 . 120.7 no C17 . C18 . C19 . 119.3(3) yes C17 . C18 . H181 . 120.3 no C19 . C18 . H181 . 120.4 no C18 . C19 . C20 . 119.7(3) yes C18 . C19 . H191 . 120.9 no C20 . C19 . H191 . 119.3 no C19 . C20 . C15 . 121.9(3) yes C19 . C20 . H201 . 119.3 no C15 . C20 . H201 . 118.8 no C14 . C21 . H211 . 109.1 no C14 . C21 . H212 . 108.9 no H211 . C21 . H212 . 109.3 no C14 . C21 . H213 . 109.9 no H211 . C21 . H213 . 110.6 no H212 . C21 . H213 . 109.1 no C5 . C22 . O23 . 110.8(2) yes C5 . C22 . C26 . 116.3(2) yes O23 . C22 . C26 . 102.9(2) yes C5 . C22 . H221 . 109.4 no O23 . C22 . H221 . 106.8 no C26 . C22 . H221 . 110.1 no C22 . O23 . C24 . 109.9(2) yes O23 . C24 . O25 . 105.0(2) yes O23 . C24 . C28 . 110.2(3) yes O25 . C24 . C28 . 108.2(2) yes O23 . C24 . C29 . 109.4(2) yes O25 . C24 . C29 . 111.1(3) yes C28 . C24 . C29 . 112.7(3) yes C24 . O25 . C26 . 106.0(2) yes C22 . C26 . O25 . 102.9(2) yes C22 . C26 . C27 . 118.2(2) yes O25 . C26 . C27 . 109.1(2) yes C22 . C26 . H261 . 109.0 no O25 . C26 . H261 . 110.2 no C27 . C26 . H261 . 107.2 no C26 . C27 . H273 . 111.0 no C26 . C27 . H272 . 109.4 no H273 . C27 . H272 . 108.3 no C26 . C27 . H271 . 109.7 no H273 . C27 . H271 . 107.9 no H272 . C27 . H271 . 110.6 no C24 . C28 . H281 . 107.8 no C24 . C28 . H282 . 110.2 no H281 . C28 . H282 . 108.3 no C24 . C28 . H283 . 110.2 no H281 . C28 . H283 . 110.3 no H282 . C28 . H283 . 110.0 no C24 . C29 . H291 . 111.6 no C24 . C29 . H292 . 109.4 no H291 . C29 . H292 . 108.8 no C24 . C29 . H293 . 107.0 no H291 . C29 . H293 . 109.5 no H292 . C29 . H293 . 110.5 no O1 . C30 . C31 . 110.9(3) yes O1 . C30 . C32 . 101.3(2) yes C31 . C30 . C32 . 110.7(3) yes O1 . C30 . C33 . 109.4(3) yes C31 . C30 . C33 . 112.9(3) yes C32 . C30 . C33 . 111.0(3) yes C30 . C31 . H313 . 108.4 no C30 . C31 . H312 . 109.1 no H313 . C31 . H312 . 110.4 no C30 . C31 . H311 . 109.3 no H313 . C31 . H311 . 108.2 no H312 . C31 . H311 . 111.4 no C30 . C32 . H321 . 109.7 no C30 . C32 . H322 . 110.0 no H321 . C32 . H322 . 108.5 no C30 . C32 . H323 . 109.7 no H321 . C32 . H323 . 110.4 no H322 . C32 . H323 . 108.5 no C30 . C33 . H331 . 110.1 no C30 . C33 . H332 . 107.4 no H331 . C33 . H332 . 110.5 no C30 . C33 . H333 . 109.3 no H331 . C33 . H333 . 110.2 no H332 . C33 . H333 . 109.3 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C4 . H41 . O25 . 129 0.97 2.57 3.267(5) yes #============================================================================== data_69 _database_code_depnum_ccdc_archive 'CCDC 846624' #TrackingRef 'CrystallographicData.cif' _ccdc_journal_depnumber ? #============================================================================== _cell_length_a 9.3260(2) _cell_length_b 13.7383(3) _cell_length_c 20.3169(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2603.07(11) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C28 H39 N1 O4 # Dc = 1.16 Fooo = 984.00 Mu = 0.76 M = 453.62 # Found Formula = C28 H39 N1 O4 # Dc = 1.16 FOOO = 984.00 Mu = 0.76 M = 453.62 _chemical_formula_sum 'C28 H39 N1 O4' _chemical_formula_moiety 'C28 H39 N1 O4' _chemical_compound_source . _chemical_formula_weight 453.62 _cell_measurement_reflns_used 3213 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.120 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_max 0.160 _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.076 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 5803 _reflns_number_total 3316 _diffrn_reflns_av_R_equivalents 0.028 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 3316 # Theoretical number of reflections is about 4700 _diffrn_reflns_theta_min 5.233 _diffrn_reflns_theta_max 27.476 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.927 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min 0 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _oxford_diffrn_Wilson_B_factor 3.00 _oxford_diffrn_Wilson_scale 2.56 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.20 _refine_diff_density_max 0.19 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 2639 _refine_ls_number_restraints 0 _refine_ls_number_parameters 298 _oxford_refine_ls_R_factor_ref 0.0451 _refine_ls_wR_factor_ref 0.0984 _refine_ls_goodness_of_fit_ref 0.9590 _refine_ls_shift/su_max 0.0003663 _refine_ls_shift/su_mean 0.0000320 # The values computed from all data _oxford_reflns_number_all 2639 _refine_ls_R_factor_all 0.0451 _refine_ls_wR_factor_all 0.0984 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2305 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_gt 0.0890 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration (3S,4R,5S,\aR) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 20.9 31.6 16.3 4.67 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.25603(17) 0.89987(11) 0.59665(8) 0.0282 1.0000 Uani . . . . . . C2 C 0.1925(3) 0.82382(17) 0.56766(11) 0.0280 1.0000 Uani . . . . . . O3 O 0.07457(19) 0.82446(13) 0.54320(9) 0.0396 1.0000 Uani . . . . . . C4 C 0.2891(3) 0.73559(16) 0.56719(12) 0.0302 1.0000 Uani . . . . . . C5 C 0.2118(2) 0.64715(16) 0.59743(11) 0.0271 1.0000 Uani . . . . . . N6 N 0.1995(2) 0.65794(14) 0.66903(9) 0.0275 1.0000 Uani . . . . . . C7 C 0.0735(2) 0.60937(17) 0.69735(13) 0.0311 1.0000 Uani . . . . . . C8 C -0.0605(2) 0.66947(17) 0.68994(12) 0.0315 1.0000 Uani . . . . . . C9 C -0.1608(3) 0.6501(2) 0.64216(14) 0.0424 1.0000 Uani . . . . . . C10 C -0.2839(3) 0.7083(3) 0.63562(18) 0.0585 1.0000 Uani . . . . . . C11 C -0.3062(4) 0.7839(2) 0.67844(19) 0.0605 1.0000 Uani . . . . . . C12 C -0.2059(3) 0.8035(2) 0.72694(18) 0.0558 1.0000 Uani . . . . . . C13 C -0.0844(3) 0.74737(19) 0.73236(14) 0.0424 1.0000 Uani . . . . . . C14 C 0.3306(3) 0.65349(18) 0.70971(12) 0.0327 1.0000 Uani . . . . . . C15 C 0.3071(3) 0.72234(18) 0.76805(11) 0.0326 1.0000 Uani . . . . . . C16 C 0.3054(3) 0.82183(19) 0.75559(12) 0.0361 1.0000 Uani . . . . . . C17 C 0.2716(3) 0.8878(2) 0.80462(13) 0.0425 1.0000 Uani . . . . . . C18 C 0.2365(3) 0.8551(2) 0.86702(13) 0.0476 1.0000 Uani . . . . . . C19 C 0.2396(4) 0.7574(2) 0.88010(13) 0.0488 1.0000 Uani . . . . . . C20 C 0.2762(3) 0.6909(2) 0.83118(12) 0.0411 1.0000 Uani . . . . . . C21 C 0.3805(3) 0.5518(2) 0.73096(15) 0.0475 1.0000 Uani . . . . . . C22 C 0.2823(3) 0.55414(16) 0.57167(11) 0.0301 1.0000 Uani . . . . . . O23 O 0.21746(19) 0.47050(11) 0.60086(9) 0.0341 1.0000 Uani . . . . . . C24 C 0.2517(3) 0.38903(18) 0.55983(14) 0.0380 1.0000 Uani . . . . . . O25 O 0.2848(2) 0.42914(12) 0.49633(9) 0.0420 1.0000 Uani . . . . . . C26 C 0.2633(3) 0.53264(17) 0.49838(13) 0.0366 1.0000 Uani . . . . . . C27 C 0.1186(3) 0.5590(2) 0.46979(14) 0.0462 1.0000 Uani . . . . . . C28 C 0.1202(4) 0.3250(2) 0.55623(18) 0.0536 1.0000 Uani . . . . . . C29 C 0.3828(3) 0.3364(2) 0.58524(17) 0.0531 1.0000 Uani . . . . . . C30 C 0.1832(3) 0.99502(16) 0.60137(12) 0.0326 1.0000 Uani . . . . . . C31 C 0.2909(3) 1.05722(18) 0.63772(15) 0.0464 1.0000 Uani . . . . . . C32 C 0.0459(3) 0.9850(2) 0.64168(13) 0.0427 1.0000 Uani . . . . . . C33 C 0.1568(4) 1.03431(19) 0.53267(14) 0.0446 1.0000 Uani . . . . . . H41 H 0.3146 0.7149 0.5216 0.0357 1.0000 Uiso R . . . . . H42 H 0.3736 0.7492 0.5933 0.0335 1.0000 Uiso R . . . . . H51 H 0.1155 0.6474 0.5770 0.0325 1.0000 Uiso R . . . . . H71 H 0.0590 0.5473 0.6766 0.0373 1.0000 Uiso R . . . . . H72 H 0.0938 0.6019 0.7438 0.0367 1.0000 Uiso R . . . . . H91 H -0.1454 0.5971 0.6117 0.0518 1.0000 Uiso R . . . . . H101 H -0.3504 0.6962 0.6025 0.0669 1.0000 Uiso R . . . . . H111 H -0.3904 0.8208 0.6764 0.0657 1.0000 Uiso R . . . . . H121 H -0.2207 0.8552 0.7545 0.0645 1.0000 Uiso R . . . . . H131 H -0.0170 0.7601 0.7649 0.0465 1.0000 Uiso R . . . . . H141 H 0.4047 0.6816 0.6827 0.0347 1.0000 Uiso R . . . . . H161 H 0.3273 0.8474 0.7119 0.0401 1.0000 Uiso R . . . . . H171 H 0.2710 0.9529 0.7960 0.0473 1.0000 Uiso R . . . . . H181 H 0.2143 0.8978 0.9005 0.0560 1.0000 Uiso R . . . . . H191 H 0.2167 0.7338 0.9215 0.0547 1.0000 Uiso R . . . . . H201 H 0.2798 0.6235 0.8396 0.0487 1.0000 Uiso R . . . . . H211 H 0.4754 0.5570 0.7522 0.0654 1.0000 Uiso R . . . . . H212 H 0.3858 0.5103 0.6932 0.0650 1.0000 Uiso R . . . . . H213 H 0.3104 0.5256 0.7612 0.0633 1.0000 Uiso R . . . . . H221 H 0.3859 0.5560 0.5824 0.0369 1.0000 Uiso R . . . . . H261 H 0.3341 0.5677 0.4697 0.0402 1.0000 Uiso R . . . . . H273 H 0.1096 0.5310 0.4260 0.0637 1.0000 Uiso R . . . . . H272 H 0.0362 0.5369 0.4954 0.0628 1.0000 Uiso R . . . . . H271 H 0.1168 0.6280 0.4651 0.0632 1.0000 Uiso R . . . . . H281 H 0.1400 0.2682 0.5296 0.0756 1.0000 Uiso R . . . . . H282 H 0.0416 0.3624 0.5362 0.0766 1.0000 Uiso R . . . . . H283 H 0.0896 0.3034 0.5996 0.0762 1.0000 Uiso R . . . . . H291 H 0.4026 0.2780 0.5598 0.0772 1.0000 Uiso R . . . . . H292 H 0.3676 0.3169 0.6305 0.0778 1.0000 Uiso R . . . . . H293 H 0.4656 0.3777 0.5835 0.0771 1.0000 Uiso R . . . . . H313 H 0.2430 1.1181 0.6481 0.0653 1.0000 Uiso R . . . . . H312 H 0.3741 1.0700 0.6091 0.0648 1.0000 Uiso R . . . . . H311 H 0.3255 1.0261 0.6778 0.0636 1.0000 Uiso R . . . . . H321 H 0.0027 1.0475 0.6385 0.0664 1.0000 Uiso R . . . . . H322 H -0.0090 0.9336 0.6215 0.0654 1.0000 Uiso R . . . . . H323 H 0.0733 0.9687 0.6864 0.0662 1.0000 Uiso R . . . . . H331 H 0.1061 1.0960 0.5335 0.0710 1.0000 Uiso R . . . . . H332 H 0.0963 0.9909 0.5083 0.0705 1.0000 Uiso R . . . . . H333 H 0.2480 1.0425 0.5101 0.0712 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0301(8) 0.0232(7) 0.0312(7) 0.0002(6) -0.0016(7) 0.0007(7) C2 0.0295(11) 0.0256(11) 0.0290(11) 0.0017(9) 0.0018(10) -0.0025(10) O3 0.0363(10) 0.0338(9) 0.0488(10) -0.0015(8) -0.0105(8) 0.0007(8) C4 0.0280(11) 0.0249(11) 0.0377(12) 0.0003(10) 0.0057(10) -0.0015(10) C5 0.0237(10) 0.0245(10) 0.0332(11) -0.0003(9) 0.0017(10) 0.0010(9) N6 0.0234(9) 0.0285(9) 0.0305(9) 0.0006(8) 0.0028(8) -0.0011(8) C7 0.0287(11) 0.0290(11) 0.0356(12) 0.0019(10) 0.0051(10) -0.0016(10) C8 0.0277(11) 0.0298(12) 0.0369(12) 0.0046(10) 0.0103(10) -0.0037(10) C9 0.0280(12) 0.0516(16) 0.0477(15) 0.0022(13) 0.0035(12) -0.0033(12) C10 0.0283(14) 0.079(2) 0.068(2) 0.0179(19) 0.0000(14) 0.0000(15) C11 0.0354(15) 0.061(2) 0.085(2) 0.0231(19) 0.0171(16) 0.0144(15) C12 0.0481(17) 0.0404(15) 0.079(2) 0.0039(15) 0.0269(17) 0.0062(14) C13 0.0398(14) 0.0381(14) 0.0492(15) -0.0021(13) 0.0132(13) 0.0027(12) C14 0.0275(11) 0.0337(12) 0.0370(13) 0.0026(11) -0.0016(10) 0.0001(11) C15 0.0305(12) 0.0358(12) 0.0316(12) 0.0023(10) -0.0042(10) -0.0002(11) C16 0.0396(13) 0.0394(13) 0.0295(11) 0.0010(10) -0.0009(11) -0.0027(12) C17 0.0500(16) 0.0395(13) 0.0381(13) -0.0056(11) -0.0006(13) -0.0031(13) C18 0.0538(17) 0.0594(17) 0.0298(12) -0.0112(12) -0.0013(13) -0.0062(16) C19 0.0558(18) 0.0637(18) 0.0271(11) 0.0070(12) -0.0009(13) -0.0093(16) C20 0.0424(15) 0.0460(14) 0.0351(12) 0.0071(12) -0.0055(12) -0.0051(13) C21 0.0447(15) 0.0400(14) 0.0578(17) 0.0000(14) -0.0091(14) 0.0137(13) C22 0.0294(12) 0.0246(11) 0.0362(12) -0.0018(10) 0.0060(10) -0.0025(10) O23 0.0385(10) 0.0214(8) 0.0425(9) -0.0020(7) 0.0104(8) -0.0004(7) C24 0.0402(13) 0.0248(11) 0.0489(14) -0.0076(11) 0.0129(12) -0.0016(11) O25 0.0519(11) 0.0299(9) 0.0443(9) -0.0079(8) 0.0154(9) -0.0007(8) C26 0.0435(14) 0.0294(12) 0.0369(12) -0.0062(10) 0.0100(12) -0.0049(11) C27 0.0538(17) 0.0429(15) 0.0418(15) -0.0063(13) -0.0028(13) -0.0041(14) C28 0.0568(18) 0.0333(14) 0.071(2) -0.0088(14) 0.0174(16) -0.0121(14) C29 0.0518(17) 0.0378(16) 0.070(2) -0.0033(14) 0.0155(16) 0.0115(14) C30 0.0402(13) 0.0233(11) 0.0344(12) -0.0005(10) -0.0020(11) 0.0044(10) C31 0.0553(17) 0.0274(12) 0.0566(16) -0.0051(12) -0.0112(15) -0.0005(13) C32 0.0429(15) 0.0457(15) 0.0395(14) -0.0034(13) 0.0026(12) 0.0124(13) C33 0.0570(18) 0.0328(13) 0.0439(14) 0.0092(12) -0.0034(13) 0.0046(13) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.6285(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.338(3) yes O1 . C30 . 1.476(3) yes C2 . O3 . 1.207(3) yes C2 . C4 . 1.510(3) yes C4 . C5 . 1.541(3) yes C4 . H41 . 0.997 no C4 . H42 . 0.969 no C5 . N6 . 1.467(3) yes C5 . C22 . 1.530(3) yes C5 . H51 . 0.989 no N6 . C7 . 1.469(3) yes N6 . C14 . 1.477(3) yes C7 . C8 . 1.505(3) yes C7 . H71 . 0.960 no C7 . H72 . 0.968 no C8 . C9 . 1.374(4) yes C8 . C13 . 1.392(4) yes C9 . C10 . 1.405(4) yes C9 . H91 . 0.967 no C10 . C11 . 1.371(5) yes C10 . H101 . 0.930 no C11 . C12 . 1.385(5) yes C11 . H111 . 0.935 no C12 . C13 . 1.375(4) yes C12 . H121 . 0.914 no C13 . H131 . 0.930 no C14 . C15 . 1.532(3) yes C14 . C21 . 1.535(3) yes C14 . H141 . 0.963 no C15 . C16 . 1.390(3) yes C15 . C20 . 1.384(3) yes C16 . C17 . 1.383(4) yes C16 . H161 . 0.976 no C17 . C18 . 1.384(4) yes C17 . H171 . 0.911 no C18 . C19 . 1.369(4) yes C18 . H181 . 0.922 no C19 . C20 . 1.392(4) yes C19 . H191 . 0.926 no C20 . H201 . 0.942 no C21 . H211 . 0.987 no C21 . H212 . 0.956 no C21 . H213 . 0.967 no C22 . O23 . 1.428(3) yes C22 . C26 . 1.528(3) yes C22 . H221 . 0.990 no O23 . C24 . 1.432(3) yes C24 . O25 . 1.436(3) yes C24 . C28 . 1.511(4) yes C24 . C29 . 1.512(4) yes O25 . C26 . 1.437(3) yes C26 . C27 . 1.513(4) yes C26 . H261 . 1.003 no C27 . H273 . 0.972 no C27 . H272 . 0.977 no C27 . H271 . 0.953 no C28 . H281 . 0.967 no C28 . H282 . 0.984 no C28 . H283 . 0.972 no C29 . H291 . 0.971 no C29 . H292 . 0.969 no C29 . H293 . 0.959 no C30 . C31 . 1.511(4) yes C30 . C32 . 1.526(4) yes C30 . C33 . 1.517(4) yes C31 . H313 . 0.972 no C31 . H312 . 0.985 no C31 . H311 . 0.974 no C32 . H321 . 0.951 no C32 . H322 . 0.964 no C32 . H323 . 0.970 no C33 . H331 . 0.970 no C33 . H332 . 0.958 no C33 . H333 . 0.973 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C30 . 121.11(18) yes O1 . C2 . O3 . 125.4(2) yes O1 . C2 . C4 . 111.44(19) yes O3 . C2 . C4 . 123.1(2) yes C2 . C4 . C5 . 110.58(19) yes C2 . C4 . H41 . 112.2 no C5 . C4 . H41 . 104.9 no C2 . C4 . H42 . 109.1 no C5 . C4 . H42 . 108.4 no H41 . C4 . H42 . 111.7 no C4 . C5 . N6 . 110.63(19) yes C4 . C5 . C22 . 108.73(18) yes N6 . C5 . C22 . 117.22(19) yes C4 . C5 . H51 . 104.8 no N6 . C5 . H51 . 110.2 no C22 . C5 . H51 . 104.5 no C5 . N6 . C7 . 113.89(19) yes C5 . N6 . C14 . 119.10(18) yes C7 . N6 . C14 . 115.11(18) yes N6 . C7 . C8 . 112.09(18) yes N6 . C7 . H71 . 110.1 no C8 . C7 . H71 . 109.0 no N6 . C7 . H72 . 105.9 no C8 . C7 . H72 . 108.5 no H71 . C7 . H72 . 111.2 no C7 . C8 . C9 . 122.0(2) yes C7 . C8 . C13 . 119.5(2) yes C9 . C8 . C13 . 118.5(2) yes C8 . C9 . C10 . 120.9(3) yes C8 . C9 . H91 . 119.8 no C10 . C9 . H91 . 119.3 no C9 . C10 . C11 . 119.7(3) yes C9 . C10 . H101 . 120.8 no C11 . C10 . H101 . 119.5 no C10 . C11 . C12 . 119.7(3) yes C10 . C11 . H111 . 120.6 no C12 . C11 . H111 . 119.6 no C11 . C12 . C13 . 120.3(3) yes C11 . C12 . H121 . 119.0 no C13 . C12 . H121 . 120.7 no C8 . C13 . C12 . 120.9(3) yes C8 . C13 . H131 . 118.5 no C12 . C13 . H131 . 120.6 no N6 . C14 . C15 . 106.80(19) yes N6 . C14 . C21 . 116.5(2) yes C15 . C14 . C21 . 112.8(2) yes N6 . C14 . H141 . 105.0 no C15 . C14 . H141 . 107.2 no C21 . C14 . H141 . 107.9 no C14 . C15 . C16 . 117.9(2) yes C14 . C15 . C20 . 123.7(2) yes C16 . C15 . C20 . 118.2(2) yes C15 . C16 . C17 . 121.0(2) yes C15 . C16 . H161 . 121.2 no C17 . C16 . H161 . 117.8 no C16 . C17 . C18 . 120.1(3) yes C16 . C17 . H171 . 120.3 no C18 . C17 . H171 . 119.6 no C17 . C18 . C19 . 119.4(3) yes C17 . C18 . H181 . 121.5 no C19 . C18 . H181 . 119.1 no C18 . C19 . C20 . 120.7(2) yes C18 . C19 . H191 . 121.0 no C20 . C19 . H191 . 118.4 no C19 . C20 . C15 . 120.5(3) yes C19 . C20 . H201 . 121.6 no C15 . C20 . H201 . 117.9 no C14 . C21 . H211 . 109.1 no C14 . C21 . H212 . 109.4 no H211 . C21 . H212 . 110.4 no C14 . C21 . H213 . 108.2 no H211 . C21 . H213 . 110.8 no H212 . C21 . H213 . 108.9 no C5 . C22 . O23 . 110.36(18) yes C5 . C22 . C26 . 116.4(2) yes O23 . C22 . C26 . 101.53(18) yes C5 . C22 . H221 . 108.8 no O23 . C22 . H221 . 110.0 no C26 . C22 . H221 . 109.4 no C22 . O23 . C24 . 107.03(17) yes O23 . C24 . O25 . 105.73(18) yes O23 . C24 . C28 . 107.6(2) yes O25 . C24 . C28 . 110.8(2) yes O23 . C24 . C29 . 110.8(2) yes O25 . C24 . C29 . 108.4(2) yes C28 . C24 . C29 . 113.2(2) yes C24 . O25 . C26 . 108.88(18) yes C22 . C26 . O25 . 101.7(2) yes C22 . C26 . C27 . 115.6(2) yes O25 . C26 . C27 . 110.5(2) yes C22 . C26 . H261 . 113.4 no O25 . C26 . H261 . 111.5 no C27 . C26 . H261 . 104.4 no C26 . C27 . H273 . 109.5 no C26 . C27 . H272 . 115.0 no H273 . C27 . H272 . 107.2 no C26 . C27 . H271 . 107.0 no H273 . C27 . H271 . 107.5 no H272 . C27 . H271 . 110.4 no C24 . C28 . H281 . 110.0 no C24 . C28 . H282 . 108.7 no H281 . C28 . H282 . 109.5 no C24 . C28 . H283 . 111.8 no H281 . C28 . H283 . 108.4 no H282 . C28 . H283 . 108.4 no C24 . C29 . H291 . 111.6 no C24 . C29 . H292 . 109.8 no H291 . C29 . H292 . 107.7 no C24 . C29 . H293 . 110.8 no H291 . C29 . H293 . 108.3 no H292 . C29 . H293 . 108.5 no O1 . C30 . C31 . 103.1(2) yes O1 . C30 . C32 . 109.93(19) yes C31 . C30 . C32 . 110.3(2) yes O1 . C30 . C33 . 109.28(19) yes C31 . C30 . C33 . 110.9(2) yes C32 . C30 . C33 . 112.9(2) yes C30 . C31 . H313 . 106.7 no C30 . C31 . H312 . 109.6 no H313 . C31 . H312 . 109.7 no C30 . C31 . H311 . 112.3 no H313 . C31 . H311 . 110.5 no H312 . C31 . H311 . 108.1 no C30 . C32 . H321 . 103.7 no C30 . C32 . H322 . 106.5 no H321 . C32 . H322 . 114.0 no C30 . C32 . H323 . 107.6 no H321 . C32 . H323 . 112.6 no H322 . C32 . H323 . 111.7 no C30 . C33 . H331 . 112.0 no C30 . C33 . H332 . 110.4 no H331 . C33 . H332 . 105.4 no C30 . C33 . H333 . 109.4 no H331 . C33 . H333 . 109.4 no H332 . C33 . H333 . 110.1 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C7 . H71 . O23 . 126 0.96 2.38 3.047(4) yes C16 . H161 . O1 . 152 0.98 2.54 3.433(4) yes C21 . H212 . O23 . 134 0.96 2.51 3.247(4) yes C32 . H322 . O3 . 126 0.96 2.32 2.990(4) yes