Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Steve Davies' _publ_contact_author_address ;Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UK ; _publ_contact_author_email steve.davies@chem.ox.ac.uk _publ_contact_author_phone 01865275646 _publ_contact_author_fax 01865275633 loop_ _publ_author_name _publ_author_address J.E.Beddow ;Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UK ; S.G.Davies ;Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UK ; K.B.Ling ;Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UK ; P.M.Roberts ;Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UK ; A.J.Russell ;Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UK ; ; A.D.Smith ; ;Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UK ; J.E.Thomson ;Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UK ; _audit_creation_date 03-23-01 _audit_creation_method CRYSTALS_ver_12-03-99 # 1231146 pr9 # Check this file using the IUCr facility at: # http://www/iucr.ac.uk/iucr-top/journals/acta/c/services/checkcif.html #**************************************************************************** # The contents of this file between this point and the next #***** line # are held in the file REFCIF.DAT # This is a character file which you may edit to reflect local conditions # # Items which need looking at are represented by a '?' # Items for which there are choices are prefixed with 'choose from' # # 1. SUBMISSION DETAILS _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Org. Biomol. Chem. The figures have been sent by mail. ; _publ_requested_category CO # choose from: FI FM FO CI CM CO AD# _publ_requested_coeditor_name ' Dr Angela Russell ' _publ_section_title ; Asymmetric synthesis of beta2-amino acids: 2-substituted-3-aminopropanoic acids from N-acryloyl SuperQuat derivatives ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? #========================================================================== data_1 _database_code_depnum_ccdc_archive 'CCDC 616167' _chemical_name_systematic # IUPAC name, in full ? _chemical_melting_point 'not measured' # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment constr #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 14.1180(3) _cell_angle_alpha 90 _cell_length_b 6.1198(2) _cell_angle_beta 108.4415(11) _cell_length_c 14.4072(4) _cell_angle_gamma 90 _cell_volume 1180.85(6) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_int_tables_number 4 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration unk 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_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum 'C26 H34 N2 O3' _chemical_formula_moiety 'C26 H34 N2 O3' _chemical_compound_source ? _chemical_formula_weight 422.57 _cell_measurement_reflns_used 2362 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 190 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 456.000 _exptl_absorpt_coefficient_mu 0.077 # Sheldrick geometric definitions 0.98 0.98 _diffrn_measurement_device_type ; Enraf Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.98 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 190 _diffrn_reflns_number 4697 _reflns_number_total 2840 _diffrn_reflns_av_R_equivalents 0.01 # Number of reflections with Friedels Law is 2840 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2704 _diffrn_reflns_theta_min 5.163 _diffrn_reflns_theta_max 27.469 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.546 _diffrn_measured_fraction_theta_full 0.963 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _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 -18 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _refine_diff_density_min -0.14 _refine_diff_density_max 0.23 _refine_ls_number_reflns 2657 _refine_ls_number_parameters 280 #_refine_ls_R_factor_ref 0.0335 _refine_ls_wR_factor_ref 0.0354 _refine_ls_goodness_of_fit_ref 1.1739 #_reflns_number_all 2840 _refine_ls_R_factor_all 0.0360 _refine_ls_wR_factor_all 0.0370 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 2657 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_gt 0.0354 _refine_ls_shift/su_max 0.000468 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 1.30 -0.462E-01 0.623 ; _diffrn_radiation_probe ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 COLLECT Software, Nonius BV 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. 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 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_attached_hydrogens # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom N1 N -0.23471(9) -0.0713(2) -0.94356(9) 0.0259 1.0000 Uani . C2 C -0.2767(1) -0.1489(3) -1.0452(1) 0.0249 1.0000 Uani . C3 C -0.18363(11) -0.1263(3) -1.07850(12) 0.0344 1.0000 Uani . O4 O -0.13143(8) 0.0595(2) -1.01872(9) 0.0395 1.0000 Uani . C5 C -0.15436(11) 0.0686(3) -0.93496(11) 0.0318 1.0000 Uani . O6 O -0.10969(9) 0.1806(2) -0.86714(9) 0.0424 1.0000 Uani . C7 C -0.20086(15) -0.0661(4) -1.18471(14) 0.0501 1.0000 Uani . C8 C -0.11687(14) -0.3250(4) -1.04923(18) 0.0549 1.0000 Uani . C9 C -0.37058(11) -0.0193(3) -1.10247(11) 0.0310 1.0000 Uani . C10 C -0.36050(15) 0.2286(3) -1.08953(14) 0.0430 1.0000 Uani . C11 C -0.46203(13) -0.0998(4) -1.07711(17) 0.0513 1.0000 Uani . C12 C -0.26478(11) -0.1619(3) -0.86783(11) 0.0285 1.0000 Uani . C13 C -0.23213(11) -0.0514(3) -0.76832(11) 0.0281 1.0000 Uani . C14 C -0.25863(12) -0.2042(3) -0.69573(11) 0.0299 1.0000 Uani . N15 N -0.23779(9) -0.1056(2) -0.59842(9) 0.0292 1.0000 Uani . C16 C -0.13098(12) -0.1190(3) -0.54309(12) 0.0333 1.0000 Uani . C17 C -0.10141(11) 0.0223(3) -0.45240(12) 0.0309 1.0000 Uani . C18 C -0.02664(12) -0.0451(3) -0.36819(12) 0.0358 1.0000 Uani . C19 C 0.00365(13) 0.0877(4) -0.28605(13) 0.0412 1.0000 Uani . C20 C -0.04087(14) 0.2898(3) -0.28652(13) 0.0413 1.0000 Uani . C21 C -0.11537(13) 0.3586(3) -0.36955(14) 0.0405 1.0000 Uani . C22 C -0.14506(13) 0.2261(3) -0.45205(13) 0.0374 1.0000 Uani . C23 C -0.29751(12) -0.2126(3) -0.54453(11) 0.0317 1.0000 Uani . C24 C -0.40842(11) -0.1653(3) -0.5868(1) 0.0291 1.0000 Uani . C25 C -0.44275(12) 0.0402(3) -0.62400(12) 0.0338 1.0000 Uani . C26 C -0.54480(13) 0.0834(3) -0.65994(13) 0.0392 1.0000 Uani . C27 C -0.61319(13) -0.0778(4) -0.65841(13) 0.0412 1.0000 Uani . C28 C -0.57968(13) -0.2823(4) -0.62055(13) 0.0409 1.0000 Uani . C29 C -0.47788(13) -0.3252(3) -0.58553(11) 0.0352 1.0000 Uani . C30 C -0.28467(16) 0.1698(3) -0.77621(13) 0.0424 1.0000 Uani . O31 O -0.3188(1) -0.3204(2) -0.88602(9) 0.0456 1.0000 Uani . H21 H -0.3053 -0.3022 -1.0545 0.0309 1.0000 Uiso . H71 H -0.1378 -0.0519 -1.2001 0.0709 1.0000 Uiso . H72 H -0.2451 -0.1786 -1.2294 0.0709 1.0000 Uiso . H73 H -0.2384 0.0800 -1.2000 0.0709 1.0000 Uiso . H81 H -0.0566 -0.3085 -1.0709 0.0688 1.0000 Uiso . H82 H -0.1547 -0.4592 -1.0806 0.0688 1.0000 Uiso . H83 H -0.0949 -0.3437 -0.9763 0.0688 1.0000 Uiso . H91 H -0.3797 -0.0487 -1.1732 0.0388 1.0000 Uiso . H101 H -0.4229 0.3022 -1.1289 0.0539 1.0000 Uiso . H102 H -0.3033 0.2813 -1.1118 0.0539 1.0000 Uiso . H103 H -0.3453 0.2670 -1.0187 0.0539 1.0000 Uiso . H111 H -0.5225 -0.0146 -1.1141 0.0656 1.0000 Uiso . H112 H -0.4738 -0.2589 -1.0929 0.0656 1.0000 Uiso . H113 H -0.4505 -0.0796 -1.0046 0.0656 1.0000 Uiso . H131 H -0.1584 -0.0242 -0.7446 0.0347 1.0000 Uiso . H141 H -0.3315 -0.2401 -0.7222 0.0374 1.0000 Uiso . H142 H -0.2189 -0.3421 -0.6898 0.0374 1.0000 Uiso . H161 H -0.0908 -0.0722 -0.5858 0.0414 1.0000 Uiso . H162 H -0.1133 -0.2743 -0.5218 0.0414 1.0000 Uiso . H181 H 0.0061 -0.1927 -0.3677 0.0432 1.0000 Uiso . H191 H 0.0579 0.0382 -0.2253 0.0498 1.0000 Uiso . H201 H -0.0184 0.3861 -0.2270 0.0493 1.0000 Uiso . H211 H -0.1498 0.5027 -0.3696 0.0506 1.0000 Uiso . H221 H -0.1983 0.2780 -0.5127 0.0454 1.0000 Uiso . H231 H -0.2865 -0.3747 -0.5445 0.0411 1.0000 Uiso . H232 H -0.2733 -0.1596 -0.4744 0.0411 1.0000 Uiso . H251 H -0.3927 0.1582 -0.6242 0.0434 1.0000 Uiso . H261 H -0.5698 0.2315 -0.6892 0.0474 1.0000 Uiso . H271 H -0.6873 -0.0446 -0.6821 0.0516 1.0000 Uiso . H281 H -0.6293 -0.3992 -0.6198 0.0496 1.0000 Uiso . H291 H -0.4543 -0.4723 -0.5578 0.0436 1.0000 Uiso . H301 H -0.2646 0.2447 -0.7111 0.0571 1.0000 Uiso . H302 H -0.2678 0.2650 -0.8251 0.0571 1.0000 Uiso . H303 H -0.3596 0.1472 -0.7983 0.0571 1.0000 Uiso . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0227(5) 0.0275(7) 0.0254(6) -0.0003(5) 0.0044(4) -0.0045(5) C2 0.0205(6) 0.0264(7) 0.0274(7) -0.0020(6) 0.0070(5) -0.0016(6) C3 0.0249(7) 0.0404(9) 0.0401(8) -0.0037(8) 0.0134(6) -0.0043(7) O4 0.0297(5) 0.0505(8) 0.0391(6) -0.0023(6) 0.0121(5) -0.0166(6) C5 0.0253(7) 0.0346(9) 0.0325(8) 0.0052(7) 0.0047(6) -0.0069(7) O6 0.0400(6) 0.0455(8) 0.0359(6) -0.0011(6) 0.0037(5) -0.0201(6) C7 0.047(1) 0.0707(15) 0.0406(9) -0.008(1) 0.0250(8) -0.0163(11) C8 0.0328(9) 0.0604(14) 0.0741(14) -0.0042(12) 0.0207(9) 0.012(1) C9 0.0246(7) 0.0342(9) 0.0296(7) -0.0051(7) 0.0022(6) 0.0016(7) C10 0.048(1) 0.033(1) 0.0421(9) 0.0032(8) 0.0059(8) 0.0068(8) C11 0.0214(7) 0.0547(13) 0.0751(14) -0.0031(11) 0.0115(8) 0.0008(8) C12 0.0283(7) 0.0268(8) 0.0302(7) 0.0008(6) 0.0091(6) -0.0029(6) C13 0.0299(7) 0.0255(7) 0.0275(7) 0.0016(6) 0.0069(6) -0.0013(6) C14 0.0354(7) 0.0254(8) 0.0293(7) 0.0002(6) 0.0107(6) -0.0006(7) N15 0.0293(6) 0.0309(7) 0.0267(6) 0.0014(5) 0.0079(5) 0.0022(6) C16 0.0285(7) 0.0364(9) 0.0337(8) 0.0005(7) 0.0079(6) 0.0063(7) C17 0.0276(7) 0.0325(9) 0.0321(7) 0.0044(7) 0.0089(6) 0.0002(7) C18 0.0293(7) 0.0375(9) 0.0386(8) 0.0079(8) 0.0080(6) 0.0005(7) C19 0.0338(8) 0.0502(11) 0.0338(8) 0.0071(8) 0.0026(6) -0.0070(8) C20 0.0386(8) 0.0485(11) 0.0363(8) -0.0057(8) 0.0113(7) -0.0152(9) C21 0.0405(9) 0.0350(9) 0.0455(9) -0.0027(8) 0.0127(7) -0.0010(8) C22 0.0362(8) 0.0356(9) 0.0354(8) 0.0012(7) 0.0042(6) 0.0034(7) C23 0.0342(7) 0.0312(8) 0.0300(7) 0.0060(7) 0.0105(6) 0.0036(7) C24 0.0326(7) 0.0332(8) 0.0224(7) 0.0009(6) 0.0099(6) 0.0007(7) C25 0.0351(8) 0.0318(9) 0.0362(8) 0.0023(7) 0.0138(6) 0.0023(7) C26 0.0406(9) 0.041(1) 0.0359(8) 0.0031(8) 0.0112(7) 0.0084(8) C27 0.0320(8) 0.0566(12) 0.0330(8) -0.0019(8) 0.0074(6) 0.0017(8) C28 0.0395(9) 0.0473(11) 0.0343(8) -0.0024(8) 0.0094(7) -0.0116(8) C29 0.0415(8) 0.0343(9) 0.0283(7) 0.0016(7) 0.0088(6) -0.0040(8) C30 0.0607(11) 0.0277(9) 0.0402(9) 0.0044(8) 0.0180(8) 0.0082(9) O31 0.0590(8) 0.0438(8) 0.0368(6) -0.0063(6) 0.0192(6) -0.0265(7) _refine_ls_extinction_method None 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 N1 . C2 . 1.4741(19) yes N1 . C5 . 1.3951(19) yes N1 . C12 . 1.4040(19) yes C2 . C3 . 1.541(2) yes C2 . C9 . 1.541(2) yes C2 . H21 . 1.013 no C3 . O4 . 1.475(2) yes C3 . C7 . 1.517(3) yes C3 . C8 . 1.514(3) yes O4 . C5 . 1.346(2) yes C5 . O6 . 1.197(2) yes C7 . H71 . 0.987 no C7 . H72 . 1.012 no C7 . H73 . 1.027 no C8 . H81 . 1.001 no C8 . H82 . 1.006 no C8 . H83 . 1.004 no C9 . C10 . 1.530(3) yes C9 . C11 . 1.530(2) yes C9 . H91 . 1.003 no C10 . H101 . 0.992 no C10 . H102 . 1.012 no C10 . H103 . 1.003 no C11 . H111 . 0.998 no C11 . H112 . 1.002 no C11 . H113 . 1.013 no C12 . C13 . 1.519(2) yes C12 . O31 . 1.211(2) yes C13 . C14 . 1.535(2) yes C13 . C30 . 1.530(2) yes C13 . H131 . 1.001 no C14 . N15 . 1.468(2) yes C14 . H141 . 1.002 no C14 . H142 . 1.002 no N15 . C16 . 1.4682(19) yes N15 . C23 . 1.468(2) yes C16 . C17 . 1.511(2) yes C16 . H161 . 1.002 no C16 . H162 . 1.006 no C17 . C18 . 1.395(2) yes C17 . C22 . 1.392(2) yes C18 . C19 . 1.387(3) yes C18 . H181 . 1.014 no C19 . C20 . 1.386(3) yes C19 . H191 . 1.010 no C20 . C21 . 1.385(3) yes C20 . H201 . 1.005 no C21 . C22 . 1.390(3) yes C21 . H211 . 1.007 no C22 . H221 . 1.007 no C23 . C24 . 1.518(2) yes C23 . H231 . 1.004 no C23 . H232 . 1.012 no C24 . C25 . 1.393(2) yes C24 . C29 . 1.390(2) yes C25 . C26 . 1.393(2) yes C25 . H251 . 1.011 no C26 . C27 . 1.385(3) yes C26 . H261 . 1.014 no C27 . C28 . 1.387(3) yes C27 . H271 . 1.013 no C28 . C29 . 1.389(3) yes C28 . H281 . 1.005 no C29 . H291 . 0.998 no C30 . H301 . 1.001 no C30 . H302 . 0.999 no C30 . H303 . 1.014 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 . N1 . C5 . 110.26(12) yes C2 . N1 . C12 . 121.30(12) yes C5 . N1 . C12 . 127.63(13) yes N1 . C2 . C3 . 99.53(11) yes N1 . C2 . C9 . 111.95(13) yes C3 . C2 . C9 . 117.47(13) yes N1 . C2 . H21 . 116.552 no C3 . C2 . H21 . 112.670 no C9 . C2 . H21 . 99.605 no C2 . C3 . O4 . 101.84(12) yes C2 . C3 . C7 . 117.08(14) yes O4 . C3 . C7 . 107.01(16) yes C2 . C3 . C8 . 111.01(16) yes O4 . C3 . C8 . 107.72(14) yes C7 . C3 . C8 . 111.29(17) yes C3 . O4 . C5 . 109.75(12) yes N1 . C5 . O4 . 108.32(13) yes N1 . C5 . O6 . 128.88(15) yes O4 . C5 . O6 . 122.80(14) yes C3 . C7 . H71 . 112.347 no C3 . C7 . H72 . 110.281 no H71 . C7 . H72 . 109.604 no C3 . C7 . H73 . 109.590 no H71 . C7 . H73 . 108.381 no H72 . C7 . H73 . 106.446 no C3 . C8 . H81 . 110.369 no C3 . C8 . H82 . 109.600 no H81 . C8 . H82 . 108.965 no C3 . C8 . H83 . 110.002 no H81 . C8 . H83 . 109.137 no H82 . C8 . H83 . 108.736 no C2 . C9 . C10 . 114.46(14) yes C2 . C9 . C11 . 110.76(15) yes C10 . C9 . C11 . 110.06(16) yes C2 . C9 . H91 . 105.309 no C10 . C9 . H91 . 106.186 no C11 . C9 . H91 . 109.800 no C9 . C10 . H101 . 110.394 no C9 . C10 . H102 . 109.276 no H101 . C10 . H102 . 109.152 no C9 . C10 . H103 . 109.740 no H101 . C10 . H103 . 109.916 no H102 . C10 . H103 . 108.325 no C9 . C11 . H111 . 110.373 no C9 . C11 . H112 . 110.522 no H111 . C11 . H112 . 109.464 no C9 . C11 . H113 . 109.524 no H111 . C11 . H113 . 108.595 no H112 . C11 . H113 . 108.312 no N1 . C12 . C13 . 118.80(13) yes N1 . C12 . O31 . 118.22(14) yes C13 . C12 . O31 . 122.92(14) yes C12 . C13 . C14 . 107.77(13) yes C12 . C13 . C30 . 109.17(13) yes C14 . C13 . C30 . 111.89(13) yes C12 . C13 . H131 . 111.605 no C14 . C13 . H131 . 108.641 no C30 . C13 . H131 . 107.802 no C13 . C14 . N15 . 112.44(13) yes C13 . C14 . H141 . 108.458 no N15 . C14 . H141 . 108.931 no C13 . C14 . H142 . 108.693 no N15 . C14 . H142 . 109.119 no H141 . C14 . H142 . 109.147 no C14 . N15 . C16 . 110.90(12) yes C14 . N15 . C23 . 110.29(13) yes C16 . N15 . C23 . 110.55(12) yes N15 . C16 . C17 . 113.14(13) yes N15 . C16 . H161 . 109.538 no C17 . C16 . H161 . 108.207 no N15 . C16 . H162 . 109.362 no C17 . C16 . H162 . 107.662 no H161 . C16 . H162 . 108.833 no C16 . C17 . C18 . 120.59(16) yes C16 . C17 . C22 . 120.95(14) yes C18 . C17 . C22 . 118.41(16) yes C17 . C18 . C19 . 120.88(18) yes C17 . C18 . H181 . 119.193 no C19 . C18 . H181 . 119.928 no C18 . C19 . C20 . 120.10(16) yes C18 . C19 . H191 . 120.584 no C20 . C19 . H191 . 119.316 no C19 . C20 . C21 . 119.66(17) yes C19 . C20 . H201 . 119.892 no C21 . C20 . H201 . 120.439 no C20 . C21 . C22 . 120.15(18) yes C20 . C21 . H211 . 120.094 no C22 . C21 . H211 . 119.726 no C17 . C22 . C21 . 120.80(16) yes C17 . C22 . H221 . 119.321 no C21 . C22 . H221 . 119.881 no N15 . C23 . C24 . 113.28(13) yes N15 . C23 . H231 . 109.038 no C24 . C23 . H231 . 109.185 no N15 . C23 . H232 . 108.441 no C24 . C23 . H232 . 108.571 no H231 . C23 . H232 . 108.202 no C23 . C24 . C25 . 121.05(15) yes C23 . C24 . C29 . 120.22(15) yes C25 . C24 . C29 . 118.68(15) yes C24 . C25 . C26 . 120.47(17) yes C24 . C25 . H251 . 119.187 no C26 . C25 . H251 . 120.339 no C25 . C26 . C27 . 120.20(18) yes C25 . C26 . H261 . 120.405 no C27 . C26 . H261 . 119.370 no C26 . C27 . C28 . 119.73(16) yes C26 . C27 . H271 . 120.178 no C28 . C27 . H271 . 120.042 no C27 . C28 . C29 . 119.90(17) yes C27 . C28 . H281 . 119.658 no C29 . C28 . H281 . 120.433 no C24 . C29 . C28 . 121.01(17) yes C24 . C29 . H291 . 119.546 no C28 . C29 . H291 . 119.434 no C13 . C30 . H301 . 110.381 no C13 . C30 . H302 . 110.477 no H301 . C30 . H302 . 109.510 no C13 . C30 . H303 . 109.613 no H301 . C30 . H303 . 108.316 no H302 . C30 . H303 . 108.492 no # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # Attachment 'CCDC616168.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 616168' _chemical_name_systematic # IUPAC name, in full ? _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment constr #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 8.6876(2) _cell_angle_alpha 90 _cell_length_b 14.8422(3) _cell_angle_beta 90 _cell_length_c 22.3552(4) _cell_angle_gamma 90 _cell_volume 2882.5(1) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 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 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration unk 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_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum 'C32 H38 N2 O4' _chemical_formula_moiety 'C32 H38 N2 O4' _chemical_compound_source ? _chemical_formula_weight 514.66 _cell_measurement_reflns_used 3585 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 190 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1104.000 _exptl_absorpt_coefficient_mu 0.078 # Sheldrick geometric definitions 0.99 0.99 _diffrn_measurement_device_type ; Enraf Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 190 _diffrn_reflns_number 6499 _reflns_number_total 3676 _diffrn_reflns_av_R_equivalents 0.01 # Number of reflections with Friedels Law is 3676 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3307 _diffrn_reflns_theta_min 5.128 _diffrn_reflns_theta_max 27.518 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.967 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _reflns_limit_h_min 0 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _refine_diff_density_min -0.14 _refine_diff_density_max 0.15 _refine_ls_number_reflns 2810 _refine_ls_number_parameters 343 #_refine_ls_R_factor_ref 0.0375 _refine_ls_wR_factor_ref 0.0433 _refine_ls_goodness_of_fit_ref 1.0991 #_reflns_number_all 3676 _refine_ls_R_factor_all 0.0528 _refine_ls_wR_factor_all 0.0560 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 2810 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_gt 0.0433 _refine_ls_shift/su_max 0.000540 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 1.00 0.451 0.609 ; _diffrn_radiation_probe ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 COLLECT Software, Nonius BV 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. 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 trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_attached_hydrogens N1 N 0.3940(2) 0.42383(11) 0.77841(7) 0.0361 1.0000 Uani . C2 C 0.3968(2) 0.45556(14) 0.71564(8) 0.0362 1.0000 Uani . C3 C 0.2554(3) 0.40338(16) 0.6913(1) 0.0438 1.0000 Uani . O4 O 0.2490(2) 0.32338(11) 0.73071(7) 0.0504 1.0000 Uani . C5 C 0.3190(3) 0.34117(15) 0.78282(9) 0.0433 1.0000 Uani . O6 O 0.3167(3) 0.29027(11) 0.82480(8) 0.0595 1.0000 Uani . C7 C 0.2659(3) 0.3674(2) 0.62748(11) 0.0590 1.0000 Uani . C8 C 0.1089(3) 0.4567(2) 0.70074(12) 0.0584 1.0000 Uani . C9 C 0.5516(3) 0.44125(16) 0.68324(9) 0.0427 1.0000 Uani . C10 C 0.6683(3) 0.51573(19) 0.69419(11) 0.0528 1.0000 Uani . C11 C 0.6236(3) 0.35024(19) 0.69664(13) 0.0603 1.0000 Uani . C12 C 0.4443(2) 0.47799(14) 0.82530(9) 0.0353 1.0000 Uani . C13 C 0.4017(2) 0.45309(14) 0.88937(8) 0.0361 1.0000 Uani . C14 C 0.3168(2) 0.53620(14) 0.91583(9) 0.0373 1.0000 Uani . C15 C 0.1758(2) 0.56125(14) 0.87989(9) 0.0363 1.0000 Uani . C16 C 0.0500(3) 0.50346(16) 0.8762(1) 0.0439 1.0000 Uani . C17 C -0.0825(3) 0.52952(19) 0.84544(11) 0.0514 1.0000 Uani . C18 C -0.0911(3) 0.61266(18) 0.81891(12) 0.0545 1.0000 Uani . C19 C 0.0345(4) 0.66948(18) 0.82129(12) 0.0591 1.0000 Uani . C20 C 0.1675(3) 0.64383(15) 0.8513(1) 0.0476 1.0000 Uani . O21 O 0.26666(19) 0.51634(11) 0.97534(6) 0.0471 1.0000 Uani . C22 C 0.5515(2) 0.43087(15) 0.92331(9) 0.0391 1.0000 Uani . N23 N 0.5216(2) 0.41140(12) 0.98712(7) 0.0383 1.0000 Uani . C24 C 0.4604(3) 0.31968(15) 0.9959(1) 0.0460 1.0000 Uani . C25 C 0.3853(3) 0.30831(15) 1.0560(1) 0.0485 1.0000 Uani . C26 C 0.2395(3) 0.34432(16) 1.06639(11) 0.0525 1.0000 Uani . C27 C 0.1689(4) 0.3350(2) 1.12181(14) 0.0726 1.0000 Uani . C28 C 0.2435(6) 0.2909(2) 1.16735(14) 0.0873 1.0000 Uani . C29 C 0.3878(6) 0.2546(2) 1.15780(15) 0.0919 1.0000 Uani . C30 C 0.4588(4) 0.26323(19) 1.10247(13) 0.0679 1.0000 Uani . C31 C 0.6639(3) 0.42278(16) 1.0229(1) 0.0457 1.0000 Uani . C32 C 0.7201(2) 0.51857(16) 1.02466(9) 0.0406 1.0000 Uani . C33 C 0.8719(3) 0.53906(18) 1.0113(1) 0.0474 1.0000 Uani . C34 C 0.9232(3) 0.6274(2) 1.01273(11) 0.0571 1.0000 Uani . C35 C 0.8240(4) 0.6962(2) 1.02707(12) 0.0607 1.0000 Uani . C36 C 0.6709(3) 0.67646(19) 1.04188(12) 0.0584 1.0000 Uani . C37 C 0.6200(3) 0.58788(18) 1.04054(11) 0.0497 1.0000 Uani . O38 O 0.5139(2) 0.54681(11) 0.81433(7) 0.0494 1.0000 Uani . H21 H 0.3879 0.5243 0.7109 0.0441 1.0000 Uiso . H71 H 0.1693 0.3331 0.6167 0.0742 1.0000 Uiso . H72 H 0.3558 0.3242 0.6235 0.0742 1.0000 Uiso . H73 H 0.2802 0.4174 0.5982 0.0742 1.0000 Uiso . H81 H 0.0166 0.4232 0.6850 0.0718 1.0000 Uiso . H82 H 0.0912 0.4700 0.7444 0.0718 1.0000 Uiso . H83 H 0.1144 0.5167 0.6789 0.0718 1.0000 Uiso . H91 H 0.5218 0.4412 0.6401 0.0550 1.0000 Uiso . H101 H 0.7674 0.5024 0.6718 0.0647 1.0000 Uiso . H102 H 0.6928 0.5217 0.7376 0.0647 1.0000 Uiso . H103 H 0.6277 0.5752 0.6791 0.0647 1.0000 Uiso . H111 H 0.7243 0.3439 0.6740 0.0774 1.0000 Uiso . H112 H 0.6463 0.3443 0.7405 0.0774 1.0000 Uiso . H113 H 0.5538 0.3002 0.6840 0.0774 1.0000 Uiso . H131 H 0.3319 0.3990 0.8935 0.0436 1.0000 Uiso . H141 H 0.3933 0.5888 0.9141 0.0480 1.0000 Uiso . H161 H 0.0571 0.4415 0.8960 0.0540 1.0000 Uiso . H171 H -0.1731 0.4866 0.8429 0.0643 1.0000 Uiso . H181 H -0.1888 0.6336 0.7978 0.0666 1.0000 Uiso . H191 H 0.0296 0.7309 0.8007 0.0708 1.0000 Uiso . H201 H 0.2618 0.6846 0.8520 0.0593 1.0000 Uiso . H221 H 0.6258 0.4830 0.9196 0.0493 1.0000 Uiso . H222 H 0.6029 0.3762 0.9042 0.0493 1.0000 Uiso . H241 H 0.5456 0.2743 0.9920 0.0579 1.0000 Uiso . H242 H 0.3811 0.3062 0.9638 0.0579 1.0000 Uiso . H261 H 0.1819 0.3780 1.0324 0.0657 1.0000 Uiso . H271 H 0.0618 0.3620 1.1290 0.0870 1.0000 Uiso . H281 H 0.1968 0.2849 1.2083 0.1093 1.0000 Uiso . H291 H 0.4464 0.2211 1.1917 0.1098 1.0000 Uiso . H301 H 0.5670 0.2357 1.0947 0.0854 1.0000 Uiso . H311 H 0.6446 0.4010 1.0649 0.0577 1.0000 Uiso . H312 H 0.7469 0.3833 1.0047 0.0577 1.0000 Uiso . H331 H 0.9462 0.4888 1.0015 0.0601 1.0000 Uiso . H341 H 1.0329 0.6401 1.0023 0.0701 1.0000 Uiso . H351 H 0.8639 0.7618 1.0253 0.0737 1.0000 Uiso . H361 H 0.5960 0.7269 1.0532 0.0755 1.0000 Uiso . H371 H 0.5096 0.5718 1.0523 0.0594 1.0000 Uiso . H211 H 0.3557 0.4894 0.9974 0.0500 1.0000 Uiso . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0405(9) 0.0388(8) 0.0291(7) -0.0015(7) -0.0010(7) 0.0016(8) C2 0.034(1) 0.044(1) 0.0303(9) 0.0021(8) -0.0022(8) 0.0026(9) C3 0.0428(11) 0.0527(12) 0.036(1) -0.0000(9) -0.004(1) -0.0020(11) O4 0.062(1) 0.0494(8) 0.0397(8) -0.0036(7) -0.0054(8) -0.0134(9) C5 0.0525(13) 0.0408(11) 0.037(1) -0.0051(9) 0.002(1) -0.001(1) O6 0.0910(13) 0.0431(8) 0.0442(9) 0.0028(7) -0.0051(9) -0.0123(9) C7 0.0575(15) 0.0812(17) 0.0384(11) -0.0091(12) -0.0098(12) -0.0060(15) C8 0.0363(11) 0.0788(17) 0.0601(14) -0.0000(14) -0.0031(11) 0.0018(13) C9 0.0386(11) 0.0573(13) 0.032(1) -0.0010(9) 0.0011(9) 0.006(1) C10 0.0363(11) 0.0728(16) 0.0494(12) 0.0029(12) 0.004(1) -0.0035(12) C11 0.0562(15) 0.0624(15) 0.0623(14) -0.0036(13) 0.0125(13) 0.0164(13) C12 0.0299(9) 0.0435(11) 0.0325(9) -0.0053(8) 0.0032(8) 0.0013(9) C13 0.034(1) 0.044(1) 0.0314(9) -0.0028(8) 0.0011(8) -0.0009(9) C14 0.036(1) 0.0449(11) 0.0315(9) -0.0055(8) 0.0011(8) 0.0025(9) C15 0.034(1) 0.042(1) 0.0322(9) -0.0052(8) 0.0024(8) 0.0020(9) C16 0.0391(11) 0.0512(12) 0.0415(11) 0.001(1) 0.0032(9) -0.003(1) C17 0.0329(11) 0.0695(15) 0.0518(13) -0.0047(12) 0.002(1) -0.0052(12) C18 0.0468(13) 0.0659(15) 0.0508(13) -0.0077(12) -0.0097(11) 0.0172(13) C19 0.0702(17) 0.0520(13) 0.0550(14) 0.0021(12) -0.0123(13) 0.0132(14) C20 0.0532(13) 0.0416(11) 0.0481(12) -0.0012(9) -0.0065(11) -0.0024(11) O21 0.0441(8) 0.067(1) 0.0299(7) -0.0030(7) 0.0024(6) 0.0155(8) C22 0.034(1) 0.0500(11) 0.0335(9) -0.0051(9) 0.0027(8) 0.004(1) N23 0.0385(9) 0.0441(9) 0.0324(8) -0.0005(7) -0.0011(7) 0.0039(8) C24 0.0542(13) 0.0408(11) 0.0429(11) -0.0051(9) 0.002(1) 0.0030(11) C25 0.0637(14) 0.0373(11) 0.0443(11) -0.0021(9) 0.0007(11) -0.0049(11) C26 0.0579(15) 0.0458(12) 0.0537(13) -0.009(1) 0.0097(12) -0.0113(12) C27 0.089(2) 0.0567(15) 0.0720(17) -0.0160(15) 0.0330(18) -0.0215(17) C28 0.146(4) 0.0592(16) 0.0562(17) 0.0023(14) 0.035(2) -0.021(2) C29 0.155(4) 0.0680(19) 0.0523(16) 0.0170(15) 0.007(2) -0.001(3) C30 0.094(2) 0.0552(15) 0.0546(15) 0.0121(12) -0.0003(15) 0.0087(16) C31 0.0410(11) 0.0548(12) 0.0412(11) -0.001(1) -0.006(1) 0.0107(11) C32 0.0374(11) 0.0554(12) 0.0291(9) -0.0041(9) -0.0044(8) 0.006(1) C33 0.0396(11) 0.0651(15) 0.038(1) -0.004(1) -0.0019(9) 0.0054(11) C34 0.0492(14) 0.0765(17) 0.0457(12) -0.0035(12) 0.0031(11) -0.0081(13) C35 0.0648(16) 0.0648(16) 0.0524(13) -0.0082(12) -0.0028(13) -0.0124(14) C36 0.0566(14) 0.0601(15) 0.0584(14) -0.0167(12) -0.0067(13) 0.0079(13) C37 0.0398(12) 0.0623(14) 0.0469(12) -0.0111(11) -0.001(1) 0.0010(11) O38 0.0525(9) 0.0559(9) 0.0397(8) -0.0039(7) 0.0064(7) -0.0179(8) _refine_ls_extinction_method None 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 N1 . C2 . 1.480(2) yes N1 . C5 . 1.393(3) yes N1 . C12 . 1.391(3) yes C2 . C3 . 1.551(3) yes C2 . C9 . 1.542(3) yes C2 . H21 . 1.029 no C3 . O4 . 1.479(3) yes C3 . C7 . 1.526(3) yes C3 . C8 . 1.514(4) yes O4 . C5 . 1.340(3) yes C5 . O6 . 1.205(3) yes C7 . H71 . 1.011 no C7 . H72 . 1.014 no C7 . H73 . 0.998 no C8 . H81 . 1.007 no C8 . H82 . 1.008 no C8 . H83 . 1.016 no C9 . C10 . 1.520(3) yes C9 . C11 . 1.518(4) yes C9 . H91 . 0.999 no C10 . H101 . 1.015 no C10 . H102 . 0.998 no C10 . H103 . 1.009 no C11 . H111 . 1.015 no C11 . H112 . 1.004 no C11 . H113 . 1.000 no C12 . C13 . 1.525(3) yes C12 . O38 . 1.212(3) yes C13 . C14 . 1.554(3) yes C13 . C22 . 1.542(3) yes C13 . H131 . 1.010 no C14 . C15 . 1.511(3) yes C14 . O21 . 1.430(2) yes C14 . H141 . 1.026 no C15 . C16 . 1.392(3) yes C15 . C20 . 1.384(3) yes C16 . C17 . 1.395(3) yes C16 . H161 . 1.022 no C17 . C18 . 1.371(4) yes C17 . H171 . 1.015 no C18 . C19 . 1.380(4) yes C18 . H181 . 1.019 no C19 . C20 . 1.390(4) yes C19 . H191 . 1.023 no C20 . H201 . 1.019 no O21 . H211 . 1.001 no C22 . N23 . 1.478(3) yes C22 . H221 . 1.011 no C22 . H222 . 1.019 no N23 . C24 . 1.475(3) yes N23 . C31 . 1.482(3) yes C24 . C25 . 1.502(3) yes C24 . H241 . 1.006 no C24 . H242 . 1.015 no C25 . C26 . 1.394(4) yes C25 . C30 . 1.392(4) yes C26 . C27 . 1.389(4) yes C26 . H261 . 1.038 no C27 . C28 . 1.373(5) yes C27 . H271 . 1.026 no C28 . C29 . 1.381(6) yes C28 . H281 . 1.006 no C29 . C30 . 1.388(5) yes C29 . H291 . 1.039 no C30 . H301 . 1.040 no C31 . C32 . 1.504(3) yes C31 . H311 . 1.006 no C31 . H312 . 1.014 no C32 . C33 . 1.386(3) yes C32 . C37 . 1.393(3) yes C33 . C34 . 1.385(4) yes C33 . H331 . 1.011 no C34 . C35 . 1.375(4) yes C34 . H341 . 0.999 no C35 . C36 . 1.401(4) yes C35 . H351 . 1.034 no C36 . C37 . 1.387(4) yes C36 . H361 . 1.024 no C37 . H371 . 1.023 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 . N1 . C5 . 110.79(16) yes C2 . N1 . C12 . 121.68(17) yes C5 . N1 . C12 . 127.05(17) yes N1 . C2 . C3 . 99.24(16) yes N1 . C2 . C9 . 114.58(17) yes C3 . C2 . C9 . 117.21(17) yes N1 . C2 . H21 . 114.363 no C3 . C2 . H21 . 113.513 no C9 . C2 . H21 . 98.850 no C2 . C3 . O4 . 102.82(16) yes C2 . C3 . C7 . 117.1(2) yes O4 . C3 . C7 . 106.15(19) yes C2 . C3 . C8 . 110.87(18) yes O4 . C3 . C8 . 107.8(2) yes C7 . C3 . C8 . 111.3(2) yes C3 . O4 . C5 . 110.02(16) yes N1 . C5 . O4 . 108.92(18) yes N1 . C5 . O6 . 128.0(2) yes O4 . C5 . O6 . 123.1(2) yes C3 . C7 . H71 . 110.484 no C3 . C7 . H72 . 110.369 no H71 . C7 . H72 . 107.471 no C3 . C7 . H73 . 111.188 no H71 . C7 . H73 . 108.717 no H72 . C7 . H73 . 108.507 no C3 . C8 . H81 . 111.254 no C3 . C8 . H82 . 111.389 no H81 . C8 . H82 . 108.279 no C3 . C8 . H83 . 110.599 no H81 . C8 . H83 . 107.590 no H82 . C8 . H83 . 107.569 no C2 . C9 . C10 . 113.95(19) yes C2 . C9 . C11 . 112.90(19) yes C10 . C9 . C11 . 109.9(2) yes C2 . C9 . H91 . 103.157 no C10 . C9 . H91 . 109.222 no C11 . C9 . H91 . 107.247 no C9 . C10 . H101 . 110.172 no C9 . C10 . H102 . 111.282 no H101 . C10 . H102 . 108.442 no C9 . C10 . H103 . 110.413 no H101 . C10 . H103 . 107.557 no H102 . C10 . H103 . 108.873 no C9 . C11 . H111 . 109.807 no C9 . C11 . H112 . 110.602 no H111 . C11 . H112 . 108.003 no C9 . C11 . H113 . 110.845 no H111 . C11 . H113 . 108.303 no H112 . C11 . H113 . 109.204 no N1 . C12 . C13 . 119.44(17) yes N1 . C12 . O38 . 119.41(18) yes C13 . C12 . O38 . 121.03(18) yes C12 . C13 . C14 . 106.28(16) yes C12 . C13 . C22 . 108.01(16) yes C14 . C13 . C22 . 112.52(16) yes C12 . C13 . H131 . 115.056 no C14 . C13 . H131 . 108.143 no C22 . C13 . H131 . 106.970 no C13 . C14 . C15 . 112.18(16) yes C13 . C14 . O21 . 109.57(16) yes C15 . C14 . O21 . 107.38(17) yes C13 . C14 . H141 . 106.370 no C15 . C14 . H141 . 108.580 no O21 . C14 . H141 . 112.847 no C14 . C15 . C16 . 121.09(18) yes C14 . C15 . C20 . 120.4(2) yes C16 . C15 . C20 . 118.5(2) yes C15 . C16 . C17 . 120.4(2) yes C15 . C16 . H161 . 118.730 no C17 . C16 . H161 . 120.845 no C16 . C17 . C18 . 120.5(2) yes C16 . C17 . H171 . 119.602 no C18 . C17 . H171 . 119.901 no C17 . C18 . C19 . 119.4(2) yes C17 . C18 . H181 . 121.289 no C19 . C18 . H181 . 119.350 no C18 . C19 . C20 . 120.6(2) yes C18 . C19 . H191 . 119.670 no C20 . C19 . H191 . 119.760 no C15 . C20 . C19 . 120.6(2) yes C15 . C20 . H201 . 118.501 no C19 . C20 . H201 . 120.877 no C14 . O21 . H211 . 107.743 no C13 . C22 . N23 . 111.63(17) yes C13 . C22 . H221 . 109.584 no N23 . C22 . H221 . 109.933 no C13 . C22 . H222 . 109.489 no N23 . C22 . H222 . 108.985 no H221 . C22 . H222 . 107.113 no C22 . N23 . C24 . 111.88(17) yes C22 . N23 . C31 . 110.63(17) yes C24 . N23 . C31 . 109.51(18) yes N23 . C24 . C25 . 112.32(17) yes N23 . C24 . H241 . 109.952 no C25 . C24 . H241 . 108.869 no N23 . C24 . H242 . 109.379 no C25 . C24 . H242 . 108.387 no H241 . C24 . H242 . 107.821 no C24 . C25 . C26 . 120.1(2) yes C24 . C25 . C30 . 121.5(3) yes C26 . C25 . C30 . 118.5(3) yes C25 . C26 . C27 . 120.8(3) yes C25 . C26 . H261 . 120.007 no C27 . C26 . H261 . 119.219 no C26 . C27 . C28 . 120.0(3) yes C26 . C27 . H271 . 120.018 no C28 . C27 . H271 . 119.927 no C27 . C28 . C29 . 120.0(3) yes C27 . C28 . H281 . 121.834 no C29 . C28 . H281 . 118.167 no C28 . C29 . C30 . 120.3(3) yes C28 . C29 . H291 . 121.217 no C30 . C29 . H291 . 118.459 no C25 . C30 . C29 . 120.4(3) yes C25 . C30 . H301 . 118.636 no C29 . C30 . H301 . 120.955 no N23 . C31 . C32 . 113.10(18) yes N23 . C31 . H311 . 109.139 no C32 . C31 . H311 . 109.502 no N23 . C31 . H312 . 108.070 no C32 . C31 . H312 . 109.058 no H311 . C31 . H312 . 107.827 no C31 . C32 . C33 . 120.7(2) yes C31 . C32 . C37 . 120.2(2) yes C33 . C32 . C37 . 119.1(2) yes C32 . C33 . C34 . 120.6(2) yes C32 . C33 . H331 . 119.527 no C34 . C33 . H331 . 119.827 no C33 . C34 . C35 . 120.4(2) yes C33 . C34 . H341 . 118.741 no C35 . C34 . H341 . 120.804 no C34 . C35 . C36 . 119.6(3) yes C34 . C35 . H351 . 118.742 no C36 . C35 . H351 . 121.605 no C35 . C36 . C37 . 119.7(3) yes C35 . C36 . H361 . 120.565 no C37 . C36 . H361 . 119.699 no C32 . C37 . C36 . 120.4(2) yes C32 . C37 . H371 . 118.563 no C36 . C37 . H371 . 120.983 no # Attachment 'CCDC616169.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 616169' _audit_creation_date 05-02-04 _audit_creation_method CRYSTALS_ver_12.50 _oxford_structure_analysis_title '2041103 pr67' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 11.5661(2) _cell_length_b 12.0490(2) _cell_length_c 20.5677(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2866.31(9) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 _symmetry_space_group_name_Hall ? 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 = C29 H40 N2 O4 # Dc = 1.11 Fooo = 1040.00 Mu = 0.74 M = 480.65 # Found Formula = C29 H40 N2 O4 # Dc = 1.11 FOOO = 1040.00 Mu = 0.74 M = 480.65 _chemical_formula_sum 'C29 H40 N2 O4' _chemical_formula_moiety 'C29 H40 N2 O4' _chemical_compound_source ? _chemical_formula_weight 480.65 _cell_measurement_reflns_used 3637 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 190 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.114 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.074 # 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 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _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 190 _diffrn_reflns_number 6489 _reflns_number_total 3648 _diffrn_reflns_av_R_equivalents 0.015 # Number of reflections with Friedels Law is 3648 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3275 _diffrn_reflns_theta_min 5.172 _diffrn_reflns_theta_max 27.479 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.929 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min 0 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.16 _refine_diff_density_max 0.16 _refine_ls_number_reflns 2582 _refine_ls_number_restraints 0 _refine_ls_number_parameters 316 #_refine_ls_R_factor_ref 0.0426 _refine_ls_wR_factor_ref 0.0502 _refine_ls_goodness_of_fit_ref 1.0963 #_reflns_number_all 3648 _refine_ls_R_factor_all 0.0676 _refine_ls_wR_factor_all 0.0661 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 2582 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_gt 0.0502 _refine_ls_shift/su_max 0.000087 # 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 unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # 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: 0.779 0.630 0.494 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Freidel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, (1997-2001) 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 atoms attached 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 N1 N 0.27444(17) 0.08474(15) 0.07919(8) 0.0328 1.0000 Uani . . . . . . C2 C 0.2212(2) 0.1082(2) 0.14331(10) 0.0378 1.0000 Uani . . . . . . C3 C 0.2041(3) 0.2345(2) 0.13688(12) 0.0449 1.0000 Uani . . . . . . O4 O 0.30173(17) 0.26587(14) 0.09440(8) 0.0447 1.0000 Uani . . . . . . C5 C 0.3342(2) 0.1793(2) 0.05800(11) 0.0379 1.0000 Uani . . . . . . O6 O 0.40554(17) 0.18595(16) 0.01560(8) 0.0491 1.0000 Uani . . . . . . C7 C 0.2129(3) 0.3026(3) 0.19854(15) 0.0636 1.0000 Uani . . . . . . C8 C 0.0933(3) 0.2606(3) 0.09957(17) 0.0652 1.0000 Uani . . . . . . C9 C 0.2981(3) 0.0674(2) 0.19950(12) 0.0501 1.0000 Uani . . . . . . C10 C 0.2945(4) -0.0593(3) 0.20471(15) 0.0685 1.0000 Uani . . . . . . C11 C 0.4238(3) 0.1073(3) 0.19574(15) 0.0640 1.0000 Uani . . . . . . C12 C 0.2435(2) -0.0089(2) 0.04375(10) 0.0349 1.0000 Uani . . . . . . C13 C 0.2928(2) -0.02594(19) -0.02406(10) 0.0354 1.0000 Uani . . . . . . C14 C 0.1924(2) -0.0401(2) -0.07342(11) 0.0378 1.0000 Uani . . . . . . C15 C 0.1054(3) 0.0556(2) -0.07502(12) 0.0475 1.0000 Uani . . . . . . C16 C 0.1585(3) 0.1656(2) -0.09636(15) 0.0608 1.0000 Uani . . . . . . C17 C 0.0035(3) 0.0244(3) -0.11879(15) 0.0641 1.0000 Uani . . . . . . O18 O 0.23824(16) -0.05214(15) -0.13714(8) 0.0436 1.0000 Uani . . . . . . C19 C 0.3654(2) -0.1329(2) -0.02008(11) 0.0391 1.0000 Uani . . . . . . N20 N 0.41954(17) -0.16107(16) -0.08281(10) 0.0369 1.0000 Uani . . . . . . C21 C 0.5259(2) -0.0946(2) -0.09159(13) 0.0475 1.0000 Uani . . . . . . C22 C 0.5723(2) -0.0971(2) -0.16002(13) 0.0475 1.0000 Uani . . . . . . C23 C 0.5146(3) -0.0424(3) -0.20958(15) 0.0590 1.0000 Uani . . . . . . C24 C 0.5604(4) -0.0407(4) -0.27267(17) 0.0790 1.0000 Uani . . . . . . C25 C 0.6624(5) -0.0928(4) -0.2858(2) 0.0904 1.0000 Uani . . . . . . C26 C 0.7200(5) -0.1476(4) -0.2377(3) 0.1012 1.0000 Uani . . . . . . C27 C 0.6755(3) -0.1496(3) -0.1743(2) 0.0770 1.0000 Uani . . . . . . C28 C 0.4486(2) -0.2806(2) -0.08601(14) 0.0457 1.0000 Uani . . . . . . C29 C 0.3456(2) -0.35590(19) -0.08051(12) 0.0397 1.0000 Uani . . . . . . C30 C 0.2439(3) -0.3390(2) -0.11497(13) 0.0463 1.0000 Uani . . . . . . C31 C 0.1507(3) -0.4112(2) -0.10782(16) 0.0554 1.0000 Uani . . . . . . C32 C 0.1589(3) -0.5023(3) -0.06742(16) 0.0618 1.0000 Uani . . . . . . C33 C 0.2592(4) -0.5204(2) -0.03408(15) 0.0653 1.0000 Uani . . . . . . C34 C 0.3512(3) -0.4483(3) -0.04005(15) 0.0568 1.0000 Uani . . . . . . O35 O 0.17856(18) -0.07582(15) 0.06758(8) 0.0508 1.0000 Uani . . . . . . H21 H 0.1424 0.0700 0.1456 0.0475 1.0000 Uiso . . . . . . H71 H 0.2023 0.3827 0.1900 0.0826 1.0000 Uiso . . . . . . H72 H 0.2921 0.2911 0.2196 0.0826 1.0000 Uiso . . . . . . H73 H 0.1532 0.2772 0.2314 0.0826 1.0000 Uiso . . . . . . H81 H 0.0819 0.3419 0.0951 0.0799 1.0000 Uiso . . . . . . H82 H 0.0242 0.2277 0.1230 0.0799 1.0000 Uiso . . . . . . H83 H 0.0964 0.2260 0.0548 0.0799 1.0000 Uiso . . . . . . H91 H 0.2638 0.0984 0.2409 0.0628 1.0000 Uiso . . . . . . H101 H 0.3461 -0.0850 0.2421 0.0880 1.0000 Uiso . . . . . . H102 H 0.3254 -0.0944 0.1637 0.0880 1.0000 Uiso . . . . . . H103 H 0.2148 -0.0877 0.2130 0.0880 1.0000 Uiso . . . . . . H111 H 0.4709 0.0786 0.2324 0.0798 1.0000 Uiso . . . . . . H112 H 0.4289 0.1901 0.1938 0.0798 1.0000 Uiso . . . . . . H113 H 0.4607 0.0777 0.1532 0.0798 1.0000 Uiso . . . . . . H131 H 0.3444 0.0386 -0.0367 0.0443 1.0000 Uiso . . . . . . H141 H 0.1489 -0.1112 -0.0618 0.0470 1.0000 Uiso . . . . . . H151 H 0.0744 0.0663 -0.0297 0.0607 1.0000 Uiso . . . . . . H161 H 0.1004 0.2266 -0.0965 0.0771 1.0000 Uiso . . . . . . H162 H 0.1928 0.1585 -0.1414 0.0771 1.0000 Uiso . . . . . . H163 H 0.2242 0.1876 -0.0659 0.0771 1.0000 Uiso . . . . . . H171 H -0.0545 0.0862 -0.1216 0.0854 1.0000 Uiso . . . . . . H172 H 0.0320 0.0085 -0.1649 0.0854 1.0000 Uiso . . . . . . H173 H -0.0366 -0.0443 -0.1027 0.0854 1.0000 Uiso . . . . . . H181 H 0.3081 -0.1007 -0.1372 0.0500 1.0000 Uiso . . . . . . H191 H 0.4252 -0.1252 0.0150 0.0497 1.0000 Uiso . . . . . . H192 H 0.3108 -0.1957 -0.0065 0.0497 1.0000 Uiso . . . . . . H211 H 0.5881 -0.1253 -0.0611 0.0590 1.0000 Uiso . . . . . . H212 H 0.5110 -0.0155 -0.0782 0.0590 1.0000 Uiso . . . . . . H231 H 0.4378 -0.0005 -0.2000 0.0740 1.0000 Uiso . . . . . . H241 H 0.5192 -0.0051 -0.3100 0.1002 1.0000 Uiso . . . . . . H251 H 0.6990 -0.0928 -0.3304 0.1206 1.0000 Uiso . . . . . . H261 H 0.7975 -0.1886 -0.2463 0.1148 1.0000 Uiso . . . . . . H271 H 0.7209 -0.1865 -0.1370 0.0940 1.0000 Uiso . . . . . . H281 H 0.4905 -0.2965 -0.1287 0.0631 1.0000 Uiso . . . . . . H282 H 0.5062 -0.2987 -0.0498 0.0631 1.0000 Uiso . . . . . . H301 H 0.2372 -0.2727 -0.1456 0.0578 1.0000 Uiso . . . . . . H311 H 0.0776 -0.3983 -0.1339 0.0698 1.0000 Uiso . . . . . . H321 H 0.0923 -0.5561 -0.0616 0.0814 1.0000 Uiso . . . . . . H331 H 0.2696 -0.5889 -0.0053 0.0771 1.0000 Uiso . . . . . . H341 H 0.4242 -0.4614 -0.0133 0.0698 1.0000 Uiso . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0400(11) 0.0342(9) 0.0241(8) -0.0014(7) 0.0050(8) -0.0036(8) C2 0.0461(14) 0.0387(12) 0.0287(10) -0.0038(9) 0.0093(10) 0.0003(12) C3 0.0553(16) 0.0428(13) 0.0365(11) -0.0025(11) 0.0052(12) 0.0066(13) O4 0.0609(11) 0.0334(8) 0.0398(8) -0.0043(7) 0.0041(9) -0.0022(8) C5 0.0456(14) 0.0361(11) 0.0320(11) -0.0004(9) -0.0028(11) -0.0058(11) O6 0.0545(11) 0.0527(11) 0.0402(9) -0.0045(8) 0.0117(9) -0.0203(9) C7 0.091(2) 0.0509(16) 0.0494(15) -0.0169(13) 0.0091(17) 0.0122(18) C8 0.064(2) 0.0606(19) 0.0705(19) 0.0001(16) 0.0010(17) 0.0217(17) C9 0.0766(19) 0.0461(14) 0.0275(10) -0.0002(10) 0.0015(13) 0.0036(15) C10 0.114(3) 0.0509(17) 0.0410(14) 0.0091(12) -0.0090(18) 0.009(2) C11 0.074(2) 0.070(2) 0.0483(15) 0.0033(15) -0.0187(16) 0.0017(18) C12 0.0393(12) 0.0369(12) 0.0284(10) -0.0011(9) 0.0027(10) -0.0045(11) C13 0.0448(13) 0.0349(11) 0.0264(10) -0.0035(8) 0.0024(10) -0.0052(11) C14 0.0455(14) 0.0410(12) 0.0269(10) -0.0040(9) -0.0001(10) 0.0010(11) C15 0.0539(16) 0.0537(15) 0.0348(12) -0.0084(11) 0.0033(12) 0.0146(13) C16 0.080(2) 0.0448(15) 0.0572(17) -0.0007(13) -0.0073(16) 0.0180(16) C17 0.0550(18) 0.084(2) 0.0535(16) -0.0140(16) -0.0054(14) 0.0203(18) O18 0.0535(11) 0.0511(10) 0.0263(7) -0.0055(7) 0.0000(7) 0.0122(9) C19 0.0440(14) 0.0439(13) 0.0294(11) -0.0010(10) -0.0018(10) 0.0000(11) N20 0.0370(11) 0.0375(10) 0.0361(10) -0.0030(8) 0.0016(9) -0.0011(9) C21 0.0419(14) 0.0529(15) 0.0477(14) -0.0088(13) 0.0022(12) -0.0103(12) C22 0.0464(15) 0.0440(14) 0.0521(14) -0.0067(12) 0.0092(12) -0.0134(13) C23 0.0521(17) 0.071(2) 0.0540(16) -0.0008(15) -0.0007(14) -0.0254(16) C24 0.088(3) 0.095(3) 0.0542(17) 0.0000(19) -0.0001(19) -0.049(2) C25 0.128(4) 0.072(2) 0.071(2) -0.012(2) 0.045(3) -0.041(3) C26 0.115(4) 0.071(2) 0.118(4) 0.003(2) 0.076(3) 0.012(3) C27 0.075(2) 0.063(2) 0.094(3) 0.0133(18) 0.042(2) 0.0095(19) C28 0.0409(13) 0.0393(13) 0.0569(15) -0.0015(12) 0.0023(12) 0.0072(11) C29 0.0483(14) 0.0305(11) 0.0404(12) -0.0041(10) 0.0064(11) 0.0064(11) C30 0.0560(16) 0.0369(12) 0.0460(13) -0.0005(11) -0.0005(13) 0.0001(12) C31 0.0534(17) 0.0466(15) 0.0663(17) -0.0107(14) 0.0003(14) -0.0053(14) C32 0.078(2) 0.0477(15) 0.0601(17) -0.0082(14) 0.0229(17) -0.0160(16) C33 0.100(3) 0.0401(15) 0.0554(17) 0.0094(12) 0.0129(18) -0.0070(18) C34 0.070(2) 0.0458(15) 0.0544(16) 0.0072(13) -0.0019(15) 0.0103(16) O35 0.0650(12) 0.0500(10) 0.0373(9) -0.0049(8) 0.0118(9) -0.0240(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4866(12) 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 N1 . C2 . 1.483(3) yes N1 . C5 . 1.402(3) yes N1 . C12 . 1.390(3) yes C2 . C3 . 1.540(3) yes C2 . C9 . 1.539(4) yes C2 . H21 . 1.022 no C3 . O4 . 1.477(3) yes C3 . C7 . 1.514(4) yes C3 . C8 . 1.527(5) yes O4 . C5 . 1.338(3) yes C5 . O6 . 1.203(3) yes C7 . H71 . 0.989 no C7 . H72 . 1.022 no C7 . H73 . 1.014 no C8 . H81 . 0.992 no C8 . H82 . 1.014 no C8 . H83 . 1.012 no C9 . C10 . 1.531(4) yes C9 . C11 . 1.533(5) yes C9 . H91 . 1.012 no C10 . H101 . 1.022 no C10 . H102 . 1.009 no C10 . H103 . 0.997 no C11 . H111 . 0.992 no C11 . H112 . 1.000 no C11 . H113 . 1.037 no C12 . C13 . 1.521(3) yes C12 . O35 . 1.206(3) yes C13 . C14 . 1.552(3) yes C13 . C19 . 1.541(4) yes C13 . H131 . 1.014 no C14 . C15 . 1.530(4) yes C14 . O18 . 1.421(3) yes C14 . H141 . 1.022 no C15 . C16 . 1.525(4) yes C15 . C17 . 1.530(4) yes C15 . H151 . 1.007 no C16 . H161 . 0.996 no C16 . H162 . 1.011 no C16 . H163 . 1.020 no C17 . H171 . 1.004 no C17 . H172 . 1.021 no C17 . H173 . 1.005 no O18 . H181 . 0.998 no C19 . N20 . 1.474(3) yes C19 . H191 . 1.004 no C19 . H192 . 1.024 no N20 . C21 . 1.479(3) yes N20 . C28 . 1.480(3) yes C21 . C22 . 1.507(4) yes C21 . H211 . 1.023 no C21 . H212 . 1.007 no C22 . C23 . 1.385(4) yes C22 . C27 . 1.383(5) yes C23 . C24 . 1.402(5) yes C23 . H231 . 1.041 no C24 . C25 . 1.363(7) yes C24 . H241 . 1.001 no C25 . C26 . 1.363(7) yes C25 . H251 . 1.010 no C26 . C27 . 1.402(5) yes C26 . H261 . 1.039 no C27 . H271 . 1.030 no C28 . C29 . 1.501(4) yes C28 . H281 . 1.022 no C28 . H282 . 1.023 no C29 . C30 . 1.388(4) yes C29 . C34 . 1.391(4) yes C30 . C31 . 1.393(4) yes C30 . H301 . 1.020 no C31 . C32 . 1.379(5) yes C31 . H311 . 1.013 no C32 . C33 . 1.366(5) yes C32 . H321 . 1.014 no C33 . C34 . 1.379(5) yes C33 . H331 . 1.021 no C34 . H341 . 1.021 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 . N1 . C5 . 109.06(18) yes C2 . N1 . C12 . 120.95(19) yes C5 . N1 . C12 . 128.55(18) yes N1 . C2 . C3 . 99.51(18) yes N1 . C2 . C9 . 111.5(2) yes C3 . C2 . C9 . 117.0(2) yes N1 . C2 . H21 . 108.994 no C3 . C2 . H21 . 109.515 no C9 . C2 . H21 . 109.728 no C2 . C3 . O4 . 101.9(2) yes C2 . C3 . C7 . 117.1(2) yes O4 . C3 . C7 . 107.8(2) yes C2 . C3 . C8 . 110.8(2) yes O4 . C3 . C8 . 106.9(2) yes C7 . C3 . C8 . 111.4(3) yes C3 . O4 . C5 . 110.24(18) yes N1 . C5 . O4 . 108.72(19) yes N1 . C5 . O6 . 128.2(2) yes O4 . C5 . O6 . 123.1(2) yes C3 . C7 . H71 . 111.824 no C3 . C7 . H72 . 109.943 no H71 . C7 . H72 . 108.537 no C3 . C7 . H73 . 110.489 no H71 . C7 . H73 . 109.223 no H72 . C7 . H73 . 106.670 no C3 . C8 . H81 . 111.196 no C3 . C8 . H82 . 110.014 no H81 . C8 . H82 . 108.950 no C3 . C8 . H83 . 110.031 no H81 . C8 . H83 . 109.141 no H82 . C8 . H83 . 107.422 no C2 . C9 . C10 . 110.8(3) yes C2 . C9 . C11 . 114.2(2) yes C10 . C9 . C11 . 110.0(3) yes C2 . C9 . H91 . 106.751 no C10 . C9 . H91 . 107.362 no C11 . C9 . H91 . 107.376 no C9 . C10 . H101 . 109.779 no C9 . C10 . H102 . 110.494 no H101 . C10 . H102 . 107.080 no C9 . C10 . H103 . 112.351 no H101 . C10 . H103 . 107.951 no H102 . C10 . H103 . 109.014 no C9 . C11 . H111 . 111.941 no C9 . C11 . H112 . 111.780 no H111 . C11 . H112 . 110.168 no C9 . C11 . H113 . 108.970 no H111 . C11 . H113 . 107.175 no H112 . C11 . H113 . 106.546 no N1 . C12 . C13 . 119.63(19) yes N1 . C12 . O35 . 119.3(2) yes C13 . C12 . O35 . 121.0(2) yes C12 . C13 . C14 . 109.5(2) yes C12 . C13 . C19 . 105.59(19) yes C14 . C13 . C19 . 110.52(19) yes C12 . C13 . H131 . 110.595 no C14 . C13 . H131 . 110.966 no C19 . C13 . H131 . 109.502 no C13 . C14 . C15 . 115.0(2) yes C13 . C14 . O18 . 109.6(2) yes C15 . C14 . O18 . 107.60(19) yes C13 . C14 . H141 . 107.911 no C15 . C14 . H141 . 108.259 no O18 . C14 . H141 . 108.262 no C14 . C15 . C16 . 113.3(2) yes C14 . C15 . C17 . 109.5(2) yes C16 . C15 . C17 . 110.7(3) yes C14 . C15 . H151 . 108.104 no C16 . C15 . H151 . 107.366 no C17 . C15 . H151 . 107.564 no C15 . C16 . H161 . 111.723 no C15 . C16 . H162 . 110.432 no H161 . C16 . H162 . 108.916 no C15 . C16 . H163 . 110.409 no H161 . C16 . H163 . 108.173 no H162 . C16 . H163 . 107.043 no C15 . C17 . H171 . 111.561 no C15 . C17 . H172 . 110.122 no H171 . C17 . H172 . 107.487 no C15 . C17 . H173 . 111.366 no H171 . C17 . H173 . 108.740 no H172 . C17 . H173 . 107.396 no C14 . O18 . H181 . 111.297 no C13 . C19 . N20 . 112.18(19) yes C13 . C19 . H191 . 109.657 no N20 . C19 . H191 . 110.914 no C13 . C19 . H192 . 107.291 no N20 . C19 . H192 . 109.355 no H191 . C19 . H192 . 107.252 no C19 . N20 . C21 . 109.62(19) yes C19 . N20 . C28 . 111.0(2) yes C21 . N20 . C28 . 109.5(2) yes N20 . C21 . C22 . 113.5(2) yes N20 . C21 . H211 . 108.337 no C22 . C21 . H211 . 108.298 no N20 . C21 . H212 . 109.721 no C22 . C21 . H212 . 109.614 no H211 . C21 . H212 . 107.118 no C21 . C22 . C23 . 120.4(3) yes C21 . C22 . C27 . 121.0(3) yes C23 . C22 . C27 . 118.5(3) yes C22 . C23 . C24 . 120.4(4) yes C22 . C23 . H231 . 120.169 no C24 . C23 . H231 . 119.413 no C23 . C24 . C25 . 120.2(4) yes C23 . C24 . H241 . 122.430 no C25 . C24 . H241 . 117.260 no C24 . C25 . C26 . 120.1(3) yes C24 . C25 . H251 . 122.806 no C26 . C25 . H251 . 117.067 no C25 . C26 . C27 . 120.3(4) yes C25 . C26 . H261 . 121.914 no C27 . C26 . H261 . 117.787 no C26 . C27 . C22 . 120.4(4) yes C26 . C27 . H271 . 120.846 no C22 . C27 . H271 . 118.685 no N20 . C28 . C29 . 113.9(2) yes N20 . C28 . H281 . 109.132 no C29 . C28 . H281 . 109.200 no N20 . C28 . H282 . 108.854 no C29 . C28 . H282 . 109.469 no H281 . C28 . H282 . 106.010 no C28 . C29 . C30 . 123.0(2) yes C28 . C29 . C34 . 119.4(3) yes C30 . C29 . C34 . 117.5(3) yes C29 . C30 . C31 . 120.7(2) yes C29 . C30 . H301 . 119.630 no C31 . C30 . H301 . 119.704 no C30 . C31 . C32 . 120.5(3) yes C30 . C31 . H311 . 119.581 no C32 . C31 . H311 . 119.892 no C31 . C32 . C33 . 119.2(3) yes C31 . C32 . H321 . 121.848 no C33 . C32 . H321 . 118.918 no C32 . C33 . C34 . 120.6(3) yes C32 . C33 . H331 . 121.307 no C34 . C33 . H331 . 118.026 no C29 . C34 . C33 . 121.4(3) yes C29 . C34 . H341 . 119.055 no C33 . C34 . H341 . 119.481 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_publ_flag O18 . H181 . N20 . 142.35(11) 1.00 1.86 yes