Supplementary Material (ESI) 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 'S. Davies' _publ_contact_author_address ; Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road OXFORD OX1 3QY UNITED KINGDOM ; _publ_contact_author_email STEVE.DAVIES@CHEM.OX.AC.UK _publ_section_title ; Diastereoselective synthesis of quaternary alpha-amino acids from diketopiperazine templates ; loop_ _publ_author_name 'S. Davies' 'A. Christopher Garner' 'Jaqueline V. A. Ouzman' 'Paul M. Roberts' 'Andrew D. Smith' ; E.J.Snow ; 'Juan A. Tamayo' 'James Thomson' 'Richard J. Vickers' data_1 _database_code_depnum_ccdc_archive 'CCDC 292510' _audit_creation_date 03-13-05 _audit_creation_method CRYSTALS_ver_12-03-99 _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 9.3443(3) _cell_angle_alpha 90 _cell_length_b 9.8498(3) _cell_angle_beta 103.8663(15) _cell_length_c 15.9297(6) _cell_angle_gamma 90 _cell_volume 1423.43(8) _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 1 21 1 ' 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 ' C30 H37 N3 O5 ' _chemical_formula_moiety ' C30 H37 N3 O5 ' _chemical_compound_source ; ? ; _chemical_formula_weight 519.64 _cell_measurement_reflns_used 3124 _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 1.212 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 556.000 _exptl_absorpt_coefficient_mu 0.083 # 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 ; USER DEFINED STRUCTURE SOLUTION ; _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 5959 _reflns_number_total 3279 _diffrn_reflns_av_R_equivalents 0.02 # Number of reflections with Friedels Law is 3279 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3140 _diffrn_reflns_theta_min 5.128 _diffrn_reflns_theta_max 27.100 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.100 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _refine_diff_density_min -0.19 _refine_diff_density_max 0.18 _refine_ls_number_reflns 2832 _refine_ls_number_parameters 343 #_refine_ls_R_factor_ref 0.0518 _refine_ls_wR_factor_ref 0.0566 _refine_ls_goodness_of_fit_ref 1.0935 #_reflns_number_all 3279 _refine_ls_R_factor_all 0.0651 _refine_ls_wR_factor_all 0.0633 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.00u(I) _reflns_number_gt 2832 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_gt 0.0566 _refine_ls_shift/su_max 0.000149 _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 1.15 0.673 0.807 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; User-defined structure solution reference 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 -0.8348(2) -0.0400(2) -0.39708(14) 0.0318 1.0000 Uani . C2 C -0.6919(3) -0.1088(3) -0.37131(17) 0.0318 1.0000 Uani . C3 C -0.5702(3) -0.0051(3) -0.35597(17) 0.0318 1.0000 Uani . N4 N -0.5754(3) 0.1158(3) -0.38120(16) 0.0374 1.0000 Uani . C5 C -0.7162(3) 0.1716(3) -0.42748(18) 0.0366 1.0000 Uani . C6 C -0.8536(3) 0.0852(3) -0.43200(17) 0.0345 1.0000 Uani . O7 O -0.9759(2) 0.1340(3) -0.46317(16) 0.0508 1.0000 Uani . C8 C -0.7377(4) 0.3108(3) -0.38667(19) 0.0399 1.0000 Uani . C9 C -0.7527(3) 0.2961(3) -0.29496(19) 0.0381 1.0000 Uani . C10 C -0.8869(3) 0.3110(3) -0.26530(18) 0.0363 1.0000 Uani . C11 C -0.8523(3) 0.2855(3) -0.17516(18) 0.0359 1.0000 Uani . N12 N -0.7006(3) 0.2552(3) -0.15135(15) 0.0390 1.0000 Uani . C13 C -0.6445(3) 0.2626(3) -0.2253(2) 0.0412 1.0000 Uani . C14 C -0.6091(3) 0.2185(4) -0.07160(19) 0.0425 1.0000 Uani . O15 O -0.6838(2) 0.2206(3) -0.01030(12) 0.0443 1.0000 Uani . C16 C -0.6061(3) 0.1980(4) 0.08264(19) 0.0448 1.0000 Uani . C17 C -0.7314(4) 0.2113(5) 0.1272(2) 0.0603 1.0000 Uani . C18 C -0.4931(4) 0.3096(5) 0.1094(2) 0.0617 1.0000 Uani . C19 C -0.5413(5) 0.0572(5) 0.0933(3) 0.0680 1.0000 Uani . O20 O -0.4813(2) 0.1914(3) -0.06322(14) 0.0551 1.0000 Uani . C21 C -0.9586(3) 0.2908(3) -0.12718(19) 0.0372 1.0000 Uani . C22 C -1.1014(3) 0.3240(3) -0.1715(2) 0.0426 1.0000 Uani . C23 C -1.1365(4) 0.3507(4) -0.2599(2) 0.0482 1.0000 Uani . C24 C -1.0313(4) 0.3435(3) -0.30725(19) 0.0429 1.0000 Uani . O25 O -0.4429(2) -0.0623(2) -0.31055(14) 0.0433 1.0000 Uani . C26 C -0.3143(4) 0.0232(5) -0.2936(3) 0.0657 1.0000 Uani . C27 C -0.6728(3) -0.2169(3) -0.4389(2) 0.0454 1.0000 Uani . C28 C -0.6242(4) -0.1525(4) -0.5147(2) 0.0548 1.0000 Uani . C29 C -0.5683(5) -0.3302(4) -0.3977(3) 0.0701 1.0000 Uani . C30 C -0.9640(3) -0.1176(3) -0.38549(18) 0.0368 1.0000 Uani . C31 C -0.9429(3) -0.1601(3) -0.29150(19) 0.0346 1.0000 Uani . C32 C -0.9378(4) -0.2950(3) -0.2687(2) 0.0402 1.0000 Uani . C33 C -0.9144(4) -0.3350(3) -0.1821(2) 0.0424 1.0000 Uani . C34 C -0.8971(3) -0.2370(3) -0.11831(19) 0.0362 1.0000 Uani . C35 C -0.9025(3) -0.1001(3) -0.14073(19) 0.0377 1.0000 Uani . C36 C -0.9252(3) -0.0619(3) -0.2266(2) 0.0363 1.0000 Uani . O37 O -0.8731(3) -0.2635(2) -0.03175(13) 0.0470 1.0000 Uani . C38 C -0.8566(4) -0.4025(4) -0.0053(2) 0.0489 1.0000 Uani . H21 H -0.6831 -0.1603 -0.3152 0.0399 1.0000 Uiso . H51 H -0.7104 0.1760 -0.4898 0.0470 1.0000 Uiso . H81 H -0.8277 0.3574 -0.4225 0.0521 1.0000 Uiso . H82 H -0.6492 0.3707 -0.3872 0.0521 1.0000 Uiso . H131 H -0.5375 0.2445 -0.2264 0.0549 1.0000 Uiso . H171 H -0.6990 0.1997 0.1908 0.0805 1.0000 Uiso . H172 H -0.7784 0.3060 0.1153 0.0805 1.0000 Uiso . H173 H -0.8130 0.1437 0.1035 0.0805 1.0000 Uiso . H181 H -0.4376 0.2989 0.1715 0.0806 1.0000 Uiso . H182 H -0.5443 0.4011 0.1034 0.0806 1.0000 Uiso . H183 H -0.4204 0.3102 0.0721 0.0806 1.0000 Uiso . H191 H -0.4895 0.0386 0.1544 0.0873 1.0000 Uiso . H192 H -0.6235 -0.0131 0.0750 0.0873 1.0000 Uiso . H193 H -0.4709 0.0438 0.0551 0.0873 1.0000 Uiso . H211 H -0.9320 0.2698 -0.0634 0.0472 1.0000 Uiso . H221 H -1.1824 0.3289 -0.1384 0.0542 1.0000 Uiso . H231 H -1.2425 0.3770 -0.2899 0.0595 1.0000 Uiso . H241 H -1.0561 0.3606 -0.3717 0.0539 1.0000 Uiso . H261 H -0.2254 -0.0259 -0.2611 0.0785 1.0000 Uiso . H262 H -0.2943 0.0575 -0.3502 0.0785 1.0000 Uiso . H263 H -0.3303 0.1062 -0.2594 0.0785 1.0000 Uiso . H271 H -0.7739 -0.2575 -0.4627 0.0596 1.0000 Uiso . H281 H -0.6144 -0.2213 -0.5586 0.0700 1.0000 Uiso . H282 H -0.6978 -0.0805 -0.5442 0.0700 1.0000 Uiso . H283 H -0.5259 -0.1047 -0.4934 0.0700 1.0000 Uiso . H291 H -0.5578 -0.3985 -0.4413 0.0904 1.0000 Uiso . H292 H -0.6056 -0.3759 -0.3502 0.0904 1.0000 Uiso . H293 H -0.4680 -0.2902 -0.3704 0.0904 1.0000 Uiso . H301 H -1.0569 -0.0596 -0.4029 0.0489 1.0000 Uiso . H302 H -0.9802 -0.2005 -0.4240 0.0489 1.0000 Uiso . H321 H -0.9483 -0.3674 -0.3146 0.0485 1.0000 Uiso . H331 H -0.9126 -0.4341 -0.1659 0.0551 1.0000 Uiso . H351 H -0.8897 -0.0282 -0.0935 0.0476 1.0000 Uiso . H361 H -0.9287 0.0374 -0.2428 0.0443 1.0000 Uiso . H381 H -0.8382 -0.4091 0.0589 0.0646 1.0000 Uiso . H382 H -0.9430 -0.4569 -0.0338 0.0646 1.0000 Uiso . H383 H -0.7655 -0.4409 -0.0226 0.0646 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 0.0294(11) 0.0337(12) 0.0321(11) -0.001(1) 0.0071(9) -0.0027(9) C2 0.0298(13) 0.0324(13) 0.0332(13) 0.0029(11) 0.008(1) 0.0003(11) C3 0.0314(13) 0.0353(15) 0.0313(13) -0.0031(11) 0.013(1) -0.0018(11) N4 0.0372(13) 0.0389(14) 0.0387(13) 0.000(1) 0.014(1) -0.007(1) C5 0.0444(16) 0.0346(15) 0.0316(13) 0.0036(11) 0.0110(11) -0.0007(12) C6 0.0399(15) 0.0359(15) 0.0266(13) 0.0012(11) 0.0059(11) 0.0008(12) O7 0.0422(12) 0.0473(13) 0.0573(13) 0.0124(11) 0.001(1) 0.0052(11) C8 0.0521(16) 0.0317(15) 0.0376(15) 0.0040(12) 0.0139(13) -0.0007(13) C9 0.0480(15) 0.0305(14) 0.0363(14) -0.0042(12) 0.0111(12) 0.0000(12) C10 0.0442(15) 0.0286(15) 0.0358(14) -0.0042(12) 0.0089(12) -0.0016(12) C11 0.0413(15) 0.0289(14) 0.0368(14) -0.0024(12) 0.0079(12) 0.0017(12) N12 0.0397(13) 0.0456(15) 0.0329(11) -0.0042(11) 0.011(1) 0.0002(11) C13 0.0430(16) 0.0421(17) 0.0403(15) -0.0051(13) 0.0137(13) -0.0021(13) C14 0.0405(17) 0.0468(18) 0.0397(15) -0.0053(14) 0.0084(12) 0.0007(14) O15 0.036(1) 0.0627(15) 0.033(1) -0.001(1) 0.0057(8) 0.006(1) C16 0.0391(15) 0.062(2) 0.0315(14) 0.0011(14) 0.0043(11) 0.0052(15) C17 0.0539(19) 0.092(3) 0.0354(15) -0.0004(19) 0.0121(14) 0.005(2) C18 0.055(2) 0.086(3) 0.0393(17) -0.0090(19) 0.0019(14) -0.010(2) C19 0.078(3) 0.077(3) 0.054(2) 0.020(2) 0.024(2) 0.020(2) O20 0.0436(13) 0.0763(19) 0.0457(13) 0.0004(12) 0.011(1) 0.0106(12) C21 0.0404(15) 0.0310(15) 0.0388(14) -0.0026(12) 0.0067(12) -0.0002(12) C22 0.0439(16) 0.0405(17) 0.0438(16) -0.0020(13) 0.0115(13) -0.0015(14) C23 0.0445(17) 0.0490(19) 0.0483(18) -0.0011(15) 0.0054(14) 0.0050(15) C24 0.0519(17) 0.0386(16) 0.0372(15) -0.0003(13) 0.0087(13) 0.0007(14) O25 0.031(1) 0.0474(13) 0.0496(12) 0.003(1) 0.0068(9) -0.0015(9) C26 0.0340(17) 0.067(3) 0.090(3) 0.004(2) 0.0025(17) -0.0092(17) C27 0.0375(15) 0.0385(17) 0.0599(19) -0.0110(15) 0.0112(14) -0.0014(13) C28 0.060(2) 0.064(2) 0.0429(17) -0.0187(16) 0.0172(15) 0.0030(18) C29 0.079(3) 0.038(2) 0.096(3) -0.005(2) 0.026(2) 0.0133(19) C30 0.0330(14) 0.0373(15) 0.0397(14) -0.0010(12) 0.0080(11) -0.0050(12) C31 0.0279(13) 0.0376(15) 0.0390(14) -0.0027(12) 0.009(1) -0.0056(12) C32 0.0483(17) 0.0333(16) 0.0434(15) -0.0062(13) 0.0200(13) -0.0089(13) C33 0.0508(18) 0.0323(15) 0.0484(17) 0.0017(13) 0.0205(14) -0.0051(13) C34 0.0362(14) 0.0399(16) 0.0361(14) -0.0023(12) 0.0158(11) -0.0002(12) C35 0.0351(14) 0.0381(16) 0.0416(16) -0.0067(13) 0.0128(12) -0.0018(12) C36 0.0364(14) 0.0300(14) 0.0435(16) -0.0035(12) 0.0116(12) -0.0040(12) O37 0.0572(13) 0.0477(14) 0.0375(11) -0.001(1) 0.0144(9) -0.0021(11) C38 0.058(2) 0.049(2) 0.0398(16) 0.0062(15) 0.0130(14) 0.0030(16) _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 . 1.466(3) yes N1 . C6 . 1.347(4) yes N1 . C30 . 1.477(3) yes C2 . C3 . 1.504(4) yes C2 . C27 . 1.555(4) yes C2 . H21 . 1.014 no C3 . N4 . 1.255(4) yes C3 . O25 . 1.357(4) yes N4 . C5 . 1.453(4) yes C5 . C6 . 1.528(4) yes C5 . C8 . 1.551(4) yes C5 . H51 . 1.007 no C6 . O7 . 1.229(4) yes C8 . C9 . 1.508(4) yes C8 . H81 . 1.007 no C8 . H82 . 1.017 no C9 . C10 . 1.450(4) yes C9 . C13 . 1.351(4) yes C10 . C11 . 1.417(4) yes C10 . C24 . 1.392(4) yes C11 . N12 . 1.409(4) yes C11 . C21 . 1.392(4) yes N12 . C13 . 1.401(4) yes N12 . C14 . 1.398(4) yes C13 . H131 . 1.020 no C14 . O15 . 1.330(4) yes C14 . O20 . 1.200(4) yes O15 . C16 . 1.501(3) yes C16 . C17 . 1.514(5) yes C16 . C18 . 1.513(5) yes C16 . C19 . 1.506(6) yes C17 . H171 . 0.993 no C17 . H172 . 1.029 no C17 . H173 . 1.014 no C18 . H181 . 1.007 no C18 . H182 . 1.015 no C18 . H183 . 1.003 no C19 . H191 . 0.994 no C19 . H192 . 1.024 no C19 . H193 . 1.006 no C21 . C22 . 1.391(4) yes C21 . H211 . 1.007 no C22 . C23 . 1.392(5) yes C22 . H221 . 1.022 no C23 . C24 . 1.377(5) yes C23 . H231 . 1.025 no C24 . H241 . 1.011 no O25 . C26 . 1.439(4) yes C26 . H261 . 0.993 no C26 . H262 . 1.021 no C26 . H263 . 1.013 no C27 . C28 . 1.526(5) yes C27 . C29 . 1.524(6) yes C27 . H271 . 1.012 no C28 . H281 . 0.994 no C28 . H282 . 1.020 no C28 . H283 . 1.015 no C29 . H291 . 0.989 no C29 . H292 . 1.012 no C29 . H293 . 1.014 no C30 . C31 . 1.521(4) yes C30 . H301 . 1.020 no C30 . H302 . 1.011 no C31 . C32 . 1.375(4) yes C31 . C36 . 1.396(4) yes C32 . C33 . 1.399(4) yes C32 . H321 . 1.010 no C33 . C34 . 1.383(4) yes C33 . H331 . 1.009 no C34 . C35 . 1.393(4) yes C34 . O37 . 1.368(4) yes C35 . C36 . 1.385(4) yes C35 . H351 . 1.019 no C36 . H361 . 1.010 no O37 . C38 . 1.430(4) yes C38 . H381 . 0.998 no C38 . H382 . 0.984 no C38 . H383 . 1.028 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 . C6 . 124.0(2) yes C2 . N1 . C30 . 116.3(2) yes C6 . N1 . C30 . 119.7(2) yes N1 . C2 . C3 . 109.5(2) yes N1 . C2 . C27 . 111.8(2) yes C3 . C2 . C27 . 111.7(2) yes N1 . C2 . H21 . 110.717 no C3 . C2 . H21 . 107.340 no C27 . C2 . H21 . 105.675 no C2 . C3 . N4 . 128.5(3) yes C2 . C3 . O25 . 109.7(2) yes N4 . C3 . O25 . 121.8(3) yes C3 . N4 . C5 . 118.9(3) yes N4 . C5 . C6 . 117.5(2) yes N4 . C5 . C8 . 108.3(2) yes C6 . C5 . C8 . 108.7(2) yes N4 . C5 . H51 . 105.077 no C6 . C5 . H51 . 102.732 no C8 . C5 . H51 . 114.684 no N1 . C6 . C5 . 117.8(2) yes N1 . C6 . O7 . 122.8(3) yes C5 . C6 . O7 . 119.4(3) yes C5 . C8 . C9 . 111.9(2) yes C5 . C8 . H81 . 109.878 no C9 . C8 . H81 . 109.487 no C5 . C8 . H82 . 108.805 no C9 . C8 . H82 . 109.139 no H81 . C8 . H82 . 107.555 no C8 . C9 . C10 . 126.5(3) yes C8 . C9 . C13 . 126.5(3) yes C10 . C9 . C13 . 107.0(3) yes C9 . C10 . C11 . 107.9(2) yes C9 . C10 . C24 . 133.0(3) yes C11 . C10 . C24 . 119.1(3) yes C10 . C11 . N12 . 106.3(2) yes C10 . C11 . C21 . 122.0(3) yes N12 . C11 . C21 . 131.6(3) yes C11 . N12 . C13 . 108.5(2) yes C11 . N12 . C14 . 131.0(2) yes C13 . N12 . C14 . 120.4(2) yes C9 . C13 . N12 . 110.3(3) yes C9 . C13 . H131 . 124.872 no N12 . C13 . H131 . 124.865 no N12 . C14 . O15 . 110.4(2) yes N12 . C14 . O20 . 122.3(3) yes O15 . C14 . O20 . 127.3(3) yes C14 . O15 . C16 . 120.5(2) yes O15 . C16 . C17 . 101.7(2) yes O15 . C16 . C18 . 108.0(3) yes C17 . C16 . C18 . 111.8(3) yes O15 . C16 . C19 . 109.5(3) yes C17 . C16 . C19 . 111.2(3) yes C18 . C16 . C19 . 113.7(3) yes C16 . C17 . H171 . 112.811 no C16 . C17 . H172 . 109.667 no H171 . C17 . H172 . 107.697 no C16 . C17 . H173 . 111.434 no H171 . C17 . H173 . 108.853 no H172 . C17 . H173 . 106.093 no C16 . C18 . H181 . 111.160 no C16 . C18 . H182 . 109.721 no H181 . C18 . H182 . 107.772 no C16 . C18 . H183 . 111.350 no H181 . C18 . H183 . 108.672 no H182 . C18 . H183 . 108.046 no C16 . C19 . H191 . 111.595 no C16 . C19 . H192 . 109.670 no H191 . C19 . H192 . 108.031 no C16 . C19 . H193 . 110.855 no H191 . C19 . H193 . 109.430 no H192 . C19 . H193 . 107.117 no C11 . C21 . C22 . 117.0(3) yes C11 . C21 . H211 . 120.670 no C22 . C21 . H211 . 122.294 no C21 . C22 . C23 . 121.5(3) yes C21 . C22 . H221 . 119.264 no C23 . C22 . H221 . 119.243 no C22 . C23 . C24 . 121.2(3) yes C22 . C23 . H231 . 119.164 no C24 . C23 . H231 . 119.601 no C10 . C24 . C23 . 119.1(3) yes C10 . C24 . H241 . 119.074 no C23 . C24 . H241 . 121.870 no C3 . O25 . C26 . 116.3(3) yes O25 . C26 . H261 . 111.683 no O25 . C26 . H262 . 110.451 no H261 . C26 . H262 . 108.304 no O25 . C26 . H263 . 110.432 no H261 . C26 . H263 . 109.006 no H262 . C26 . H263 . 106.815 no C2 . C27 . C28 . 111.6(3) yes C2 . C27 . C29 . 111.8(3) yes C28 . C27 . C29 . 111.3(3) yes C2 . C27 . H271 . 106.157 no C28 . C27 . H271 . 107.204 no C29 . C27 . H271 . 108.469 no C27 . C28 . H281 . 111.617 no C27 . C28 . H282 . 110.964 no H281 . C28 . H282 . 108.390 no C27 . C28 . H283 . 110.244 no H281 . C28 . H283 . 108.748 no H282 . C28 . H283 . 106.721 no C27 . C29 . H291 . 110.946 no C27 . C29 . H292 . 110.364 no H291 . C29 . H292 . 109.425 no C27 . C29 . H293 . 109.377 no H291 . C29 . H293 . 109.214 no H292 . C29 . H293 . 107.439 no N1 . C30 . C31 . 110.4(2) yes N1 . C30 . H301 . 110.110 no C31 . C30 . H301 . 108.807 no N1 . C30 . H302 . 110.511 no C31 . C30 . H302 . 109.899 no H301 . C30 . H302 . 107.063 no C30 . C31 . C32 . 120.9(3) yes C30 . C31 . C36 . 120.2(3) yes C32 . C31 . C36 . 118.9(3) yes C31 . C32 . C33 . 121.3(3) yes C31 . C32 . H321 . 119.989 no C33 . C32 . H321 . 118.674 no C32 . C33 . C34 . 119.4(3) yes C32 . C33 . H331 . 120.974 no C34 . C33 . H331 . 119.622 no C33 . C34 . C35 . 119.8(3) yes C33 . C34 . O37 . 124.7(3) yes C35 . C34 . O37 . 115.5(3) yes C34 . C35 . C36 . 120.2(3) yes C34 . C35 . H351 . 119.522 no C36 . C35 . H351 . 120.243 no C31 . C36 . C35 . 120.4(3) yes C31 . C36 . H361 . 119.418 no C35 . C36 . H361 . 120.158 no C34 . O37 . C38 . 117.4(2) yes O37 . C38 . H381 . 110.141 no O37 . C38 . H382 . 111.582 no H381 . C38 . H382 . 110.913 no O37 . C38 . H383 . 108.155 no H381 . C38 . H383 . 107.418 no H382 . C38 . H383 . 108.486 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 'CCDC292511.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 292511' _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 9.4150(1) _cell_angle_alpha 90 _cell_length_b 33.8450(4) _cell_angle_beta 90 _cell_length_c 9.5680(2) _cell_angle_gamma 90 _cell_volume 3048.85(8) _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 'C31 H43 N3 O7' _chemical_formula_moiety 'C31 H43 N3 O7' _chemical_compound_source ? _chemical_formula_weight 569.70 _cell_measurement_reflns_used 5411 _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 1.241 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1224.000 _exptl_absorpt_coefficient_mu 0.088 # 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 ; USER DEFINED STRUCTURE SOLUTION ; _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 10838 _reflns_number_total 3860 _diffrn_reflns_av_R_equivalents 0.03 # Number of reflections with Friedels Law is 3860 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3492 _diffrn_reflns_theta_min 5.110 _diffrn_reflns_theta_max 27.472 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 22.939 _diffrn_measured_fraction_theta_full 0.977 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min 0 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 43 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _refine_diff_density_min -0.33 _refine_diff_density_max 0.33 _refine_ls_number_reflns 3329 _refine_ls_number_parameters 371 #_refine_ls_R_factor_ref 0.0718 _refine_ls_wR_factor_ref 0.0722 _refine_ls_goodness_of_fit_ref 0.9600 #_reflns_number_all 3860 _refine_ls_R_factor_all 0.0839 _refine_ls_wR_factor_all 0.0845 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.00u(I) _reflns_number_gt 3329 _refine_ls_R_factor_gt 0.0718 _refine_ls_wR_factor_gt 0.0722 _refine_ls_shift/su_max 0.000159 _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 1.87 0.953 1.33 ; _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 ; User-defined structure solution reference 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 C1 C -0.6732(3) -0.21534(9) -1.2187(3) 0.0247 1.0000 Uani . C2 C -0.5623(3) -0.2071(1) -1.1057(3) 0.0255 1.0000 Uani . N3 N -0.6055(3) -0.19579(8) -0.9776(3) 0.0266 1.0000 Uani . C4 C -0.7551(3) -0.1897(1) -0.9353(3) 0.0286 1.0000 Uani . C5 C -0.8519(3) -0.19642(9) -1.0588(3) 0.0243 1.0000 Uani . N6 N -0.8208(3) -0.20710(8) -1.1805(3) 0.0245 1.0000 Uani . O7 O -0.9872(2) -0.19019(8) -1.0185(3) 0.0331 1.0000 Uani . C8 C -1.0944(4) -0.19324(12) -1.1240(4) 0.0375 1.0000 Uani . C9 C -0.7736(4) -0.1485(1) -0.8657(4) 0.0319 1.0000 Uani . C10 C -0.8979(4) -0.14763(13) -0.7621(4) 0.0449 1.0000 Uani . C11 C -0.7831(5) -0.11571(12) -0.9737(4) 0.0441 1.0000 Uani . C12 C -0.5023(3) -0.1973(1) -0.8626(3) 0.0299 1.0000 Uani . C13 C -0.4201(3) -0.1596(1) -0.8326(4) 0.0297 1.0000 Uani . C14 C -0.3717(4) -0.13461(11) -0.9364(4) 0.0343 1.0000 Uani . C15 C -0.2886(4) -0.10197(12) -0.9067(4) 0.0377 1.0000 Uani . C16 C -0.2516(4) -0.09369(11) -0.7689(4) 0.0331 1.0000 Uani . C17 C -0.3013(4) -0.11750(12) -0.6634(4) 0.0408 1.0000 Uani . C18 C -0.3846(4) -0.15016(12) -0.6948(4) 0.0398 1.0000 Uani . O19 O -0.1692(3) -0.06078(8) -0.7499(3) 0.0464 1.0000 Uani . C20 C -0.1280(5) -0.05216(13) -0.6089(4) 0.0487 1.0000 Uani . O21 O -0.4345(2) -0.21277(7) -1.1320(3) 0.0324 1.0000 Uani . C22 C -0.6384(3) -0.1921(1) -1.3539(3) 0.0283 1.0000 Uani . C23 C -0.6459(3) -0.1482(1) -1.3377(3) 0.0283 1.0000 Uani . C24 C -0.5280(3) -0.1214(1) -1.3117(3) 0.0286 1.0000 Uani . C25 C -0.5828(4) -0.08320(11) -1.2925(3) 0.0307 1.0000 Uani . N26 N -0.7321(3) -0.08606(9) -1.3091(3) 0.0325 1.0000 Uani . C27 C -0.7653(4) -0.1257(1) -1.3385(4) 0.0305 1.0000 Uani . C28 C -0.8382(4) -0.05842(11) -1.2881(4) 0.0334 1.0000 Uani . O29 O -0.7855(3) -0.02480(7) -1.2416(3) 0.0391 1.0000 Uani . C30 C -0.8809(5) 0.00887(12) -1.2062(4) 0.0452 1.0000 Uani . C31 C -0.7767(6) 0.03989(13) -1.1561(5) 0.0545 1.0000 Uani . C32 C -0.9573(6) 0.02264(14) -1.3379(6) 0.0611 1.0000 Uani . C33 C -0.9810(6) -0.00295(18) -1.0906(6) 0.0684 1.0000 Uani . O34 O -0.9624(3) -0.06585(9) -1.3108(4) 0.0477 1.0000 Uani . C35 C -0.4965(4) -0.05097(11) -1.2673(4) 0.0376 1.0000 Uani . C36 C -0.3499(4) -0.05755(12) -1.2628(4) 0.0401 1.0000 Uani . C37 C -0.2930(4) -0.09522(12) -1.2808(4) 0.0370 1.0000 Uani . C38 C -0.3807(4) -0.12774(11) -1.3052(3) 0.0339 1.0000 Uani . C39 C -0.6630(3) -0.25996(9) -1.2511(4) 0.0302 1.0000 Uani . O40 O -0.2805(3) -0.2402(1) -1.3699(3) 0.0519 1.0000 Uani . O41 O -0.9787(3) -0.23082(12) -1.4345(3) 0.0600 1.0000 Uani . H41 H -0.7836 -0.2099 -0.8623 0.0363 1.0000 Uiso . H81 H -1.1907 -0.1873 -1.0840 0.0519 1.0000 Uiso . H82 H -1.0939 -0.2197 -1.1674 0.0519 1.0000 Uiso . H83 H -1.0747 -0.1726 -1.1999 0.0519 1.0000 Uiso . H91 H -0.6843 -0.1429 -0.8103 0.0406 1.0000 Uiso . H101 H -0.9063 -0.1207 -0.7197 0.0579 1.0000 Uiso . H102 H -0.9879 -0.1543 -0.8122 0.0579 1.0000 Uiso . H103 H -0.8812 -0.1675 -0.6861 0.0579 1.0000 Uiso . H111 H -0.7929 -0.0891 -0.9297 0.0567 1.0000 Uiso . H112 H -0.8659 -0.1201 -1.0389 0.0567 1.0000 Uiso . H113 H -0.6934 -0.1151 -1.0351 0.0567 1.0000 Uiso . H121 H -0.4316 -0.2188 -0.8832 0.0409 1.0000 Uiso . H122 H -0.5553 -0.2051 -0.7738 0.0409 1.0000 Uiso . H141 H -0.3953 -0.1419 -1.0377 0.0399 1.0000 Uiso . H151 H -0.2562 -0.0833 -0.9866 0.0461 1.0000 Uiso . H171 H -0.2799 -0.1114 -0.5617 0.0498 1.0000 Uiso . H181 H -0.4200 -0.1686 -0.6166 0.0462 1.0000 Uiso . H201 H -0.0682 -0.0280 -0.6013 0.0680 1.0000 Uiso . H202 H -0.0705 -0.0753 -0.5683 0.0680 1.0000 Uiso . H203 H -0.2142 -0.0490 -0.5467 0.0680 1.0000 Uiso . H221 H -0.7045 -0.2006 -1.4284 0.0353 1.0000 Uiso . H222 H -0.5376 -0.1993 -1.3824 0.0353 1.0000 Uiso . H271 H -0.8644 -0.1360 -1.3541 0.0361 1.0000 Uiso . H311 H -0.8285 0.0651 -1.1287 0.0780 1.0000 Uiso . H312 H -0.7058 0.0465 -1.2299 0.0780 1.0000 Uiso . H313 H -0.7253 0.0299 -1.0708 0.0780 1.0000 Uiso . H321 H -1.0233 0.0452 -1.3156 0.0695 1.0000 Uiso . H322 H -1.0145 0.0006 -1.3799 0.0695 1.0000 Uiso . H323 H -0.8860 0.0319 -1.4088 0.0695 1.0000 Uiso . H331 H -1.0498 0.0193 -1.0652 0.0881 1.0000 Uiso . H332 H -1.0406 -0.0268 -1.1147 0.0881 1.0000 Uiso . H333 H -0.9262 -0.0095 -1.0022 0.0881 1.0000 Uiso . H351 H -0.5400 -0.0237 -1.2553 0.0490 1.0000 Uiso . H361 H -0.2830 -0.0349 -1.2465 0.0508 1.0000 Uiso . H371 H -0.1897 -0.0991 -1.2752 0.0432 1.0000 Uiso . H381 H -0.3386 -0.1558 -1.3160 0.0408 1.0000 Uiso . H391 H -0.7329 -0.2680 -1.3220 0.0361 1.0000 Uiso . H392 H -0.5645 -0.2671 -1.2812 0.0361 1.0000 Uiso . H393 H -0.6836 -0.2755 -1.1605 0.0361 1.0000 Uiso . H401 H -0.3345 -0.2305 -1.2863 0.0620 1.0000 Uiso . H402 H -0.3564 -0.2478 -1.4366 0.0500 1.0000 Uiso . H411 H -0.9343 -0.2246 -1.3341 0.0500 1.0000 Uiso . H412 H -1.0782 -0.2252 -1.4034 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 C1 0.0190(14) 0.0304(15) 0.0247(14) -0.0049(12) 0.0021(12) -0.0037(12) C2 0.0198(14) 0.0291(15) 0.0276(15) -0.0033(12) -0.0021(12) -0.0021(11) N3 0.0154(11) 0.0364(15) 0.0281(13) -0.0031(11) -0.003(1) -0.0003(11) C4 0.0167(13) 0.0384(17) 0.0307(15) 0.0001(13) 0.0023(12) 0.0016(12) C5 0.0170(13) 0.0272(14) 0.0288(15) -0.0023(12) 0.0017(12) -0.0001(12) N6 0.0150(11) 0.0277(13) 0.0309(13) -0.0044(11) 0.0013(11) 0.000(1) O7 0.015(1) 0.0494(14) 0.0350(12) -0.0075(11) -0.0012(9) 0.003(1) C8 0.0181(14) 0.059(2) 0.0359(17) -0.0068(17) -0.0003(14) 0.0052(15) C9 0.0275(15) 0.0371(18) 0.0309(16) -0.0075(14) 0.0006(14) 0.0000(14) C10 0.0380(19) 0.057(2) 0.0393(19) -0.0146(18) 0.0106(17) 0.0023(17) C11 0.053(2) 0.0385(19) 0.041(2) -0.0029(16) -0.0028(19) 0.0019(18) C12 0.0245(15) 0.0368(18) 0.0285(15) -0.0023(13) -0.0093(13) 0.0011(13) C13 0.0236(15) 0.0369(17) 0.0285(15) -0.0052(13) -0.0029(13) 0.0033(13) C14 0.0348(18) 0.0419(19) 0.0262(15) -0.0018(13) -0.0024(14) -0.0003(15) C15 0.0389(19) 0.046(2) 0.0281(16) -0.0016(15) 0.0004(15) -0.0037(17) C16 0.0305(16) 0.0393(18) 0.0294(15) -0.0040(14) -0.0028(14) -0.0044(14) C17 0.045(2) 0.050(2) 0.0272(16) -0.0036(15) -0.0031(16) -0.0161(17) C18 0.042(2) 0.053(2) 0.0240(15) 0.0041(15) -0.0008(14) -0.0168(17) O19 0.0498(16) 0.0518(16) 0.0377(14) -0.0050(12) -0.0033(13) -0.0220(13) C20 0.050(2) 0.057(2) 0.039(2) -0.0111(18) -0.0056(18) -0.019(2) O21 0.018(1) 0.0453(14) 0.0345(12) -0.010(1) 0.0016(9) 0.0012(9) C22 0.0226(14) 0.0394(17) 0.0229(14) -0.0038(12) 0.0046(12) -0.0012(13) C23 0.0242(14) 0.0368(17) 0.0238(14) -0.0004(13) 0.0006(12) -0.0030(13) C24 0.0243(14) 0.0401(18) 0.0214(14) -0.0001(12) 0.0053(12) -0.0049(13) C25 0.0246(15) 0.0407(19) 0.0269(15) 0.0045(13) -0.0050(13) -0.0065(13) N26 0.0243(13) 0.0331(15) 0.0399(16) 0.0041(12) -0.0045(12) -0.0044(11) C27 0.0244(15) 0.0311(17) 0.0360(17) 0.0001(14) -0.0037(13) -0.0069(13) C28 0.0259(16) 0.0408(19) 0.0334(17) 0.0021(14) -0.0013(14) -0.0049(14) O29 0.0331(12) 0.0360(13) 0.0481(15) -0.0011(11) -0.0057(12) -0.0002(11) C30 0.050(2) 0.042(2) 0.044(2) -0.0114(16) -0.0086(18) 0.0111(18) C31 0.059(3) 0.045(2) 0.059(3) -0.013(2) -0.013(2) 0.008(2) C32 0.068(3) 0.051(3) 0.064(3) -0.007(2) -0.024(3) 0.020(2) C33 0.055(3) 0.092(4) 0.058(3) -0.023(3) 0.015(3) -0.004(3) O34 0.0266(12) 0.0526(17) 0.0639(19) -0.0060(15) -0.0070(13) 0.0003(12) C35 0.0304(17) 0.0408(19) 0.0416(19) 0.0014(16) -0.0035(16) -0.0077(14) C36 0.0327(18) 0.049(2) 0.0390(19) 0.0062(17) -0.0041(16) -0.0166(16) C37 0.0199(14) 0.055(2) 0.0363(18) 0.0037(16) -0.0014(14) -0.0069(15) C38 0.0267(16) 0.048(2) 0.0273(16) 0.0077(15) 0.0030(13) -0.0044(14) C39 0.0217(13) 0.0316(16) 0.0374(17) -0.0043(14) -0.0012(14) -0.0003(12) O40 0.0265(12) 0.086(2) 0.0437(16) -0.0193(15) 0.0017(12) 0.0003(14) O41 0.0294(13) 0.113(3) 0.0380(15) -0.0219(16) -0.0020(12) 0.0023(16) _refine_ls_extinction_coef 1073.3(2290) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' 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 C1 . C2 . 1.529(4) yes C1 . N6 . 1.464(4) yes C1 . C22 . 1.549(4) yes C1 . C39 . 1.545(4) yes C2 . N3 . 1.346(4) yes C2 . O21 . 1.245(4) yes N3 . C4 . 1.480(4) yes N3 . C12 . 1.469(4) yes C4 . C5 . 1.510(4) yes C4 . C9 . 1.555(5) yes C4 . H41 . 1.014 no C5 . N6 . 1.254(4) yes C5 . O7 . 1.347(4) yes O7 . C8 . 1.432(4) yes C8 . H81 . 1.003 no C8 . H82 . 0.988 no C8 . H83 . 1.024 no C9 . C10 . 1.535(5) yes C9 . C11 . 1.518(6) yes C9 . H91 . 1.012 no C10 . H101 . 1.001 no C10 . H102 . 0.999 no C10 . H103 . 1.002 no C11 . H111 . 1.000 no C11 . H112 . 1.009 no C11 . H113 . 1.028 no C12 . C13 . 1.520(5) yes C12 . H121 . 1.007 no C12 . H122 . 1.020 no C13 . C14 . 1.381(5) yes C13 . C18 . 1.397(5) yes C14 . C15 . 1.383(5) yes C14 . H141 . 1.025 no C15 . C16 . 1.392(5) yes C15 . H151 . 1.038 no C16 . C17 . 1.374(5) yes C16 . O19 . 1.370(4) yes C17 . C18 . 1.388(5) yes C17 . H171 . 1.015 no C18 . H181 . 1.030 no O19 . C20 . 1.434(5) yes C20 . H201 . 0.996 no C20 . H202 . 1.028 no C20 . H203 . 1.012 no C22 . C23 . 1.495(5) yes C22 . H221 . 0.989 no C22 . H222 . 1.017 no C23 . C24 . 1.455(4) yes C23 . C27 . 1.357(5) yes C24 . C25 . 1.405(5) yes C24 . C38 . 1.404(5) yes C25 . N26 . 1.418(4) yes C25 . C35 . 1.381(5) yes N26 . C27 . 1.406(5) yes N26 . C28 . 1.383(5) yes C27 . H271 . 1.008 no C28 . O29 . 1.319(4) yes C28 . O34 . 1.216(4) yes O29 . C30 . 1.490(5) yes C30 . C31 . 1.515(6) yes C30 . C32 . 1.523(6) yes C30 . C33 . 1.507(7) yes C31 . H311 . 1.017 no C31 . H312 . 0.998 no C31 . H313 . 1.006 no C32 . H321 . 1.007 no C32 . H322 . 1.005 no C32 . H323 . 1.005 no C33 . H331 . 1.022 no C33 . H332 . 1.011 no C33 . H333 . 1.015 no C35 . C36 . 1.399(5) yes C35 . H351 . 1.015 no C36 . C37 . 1.394(6) yes C36 . H361 . 1.004 no C37 . C38 . 1.396(5) yes C37 . H371 . 0.982 no C38 . H381 . 1.034 no C39 . H391 . 0.983 no C39 . H392 . 1.001 no C39 . H393 . 1.031 no O40 . H401 . 1.002 no O40 . H402 . 0.992 no O41 . H411 . 1.069 no O41 . H412 . 1.001 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 . C1 . N6 . 115.9(3) yes C2 . C1 . C22 . 110.7(2) yes N6 . C1 . C22 . 108.2(3) yes C2 . C1 . C39 . 106.2(3) yes N6 . C1 . C39 . 107.2(2) yes C22 . C1 . C39 . 108.4(3) yes C1 . C2 . N3 . 119.3(3) yes C1 . C2 . O21 . 119.2(3) yes N3 . C2 . O21 . 121.4(3) yes C2 . N3 . C4 . 125.2(3) yes C2 . N3 . C12 . 118.2(3) yes C4 . N3 . C12 . 115.4(3) yes N3 . C4 . C5 . 109.8(3) yes N3 . C4 . C9 . 110.4(3) yes C5 . C4 . C9 . 113.8(3) yes N3 . C4 . H41 . 110.228 no C5 . C4 . H41 . 106.092 no C9 . C4 . H41 . 106.269 no C4 . C5 . N6 . 129.0(3) yes C4 . C5 . O7 . 108.8(3) yes N6 . C5 . O7 . 122.2(3) yes C1 . N6 . C5 . 120.6(3) yes C5 . O7 . C8 . 117.0(3) yes O7 . C8 . H81 . 110.745 no O7 . C8 . H82 . 111.007 no H81 . C8 . H82 . 110.209 no O7 . C8 . H83 . 108.833 no H81 . C8 . H83 . 107.387 no H82 . C8 . H83 . 108.552 no C4 . C9 . C10 . 112.2(3) yes C4 . C9 . C11 . 111.7(3) yes C10 . C9 . C11 . 112.4(3) yes C4 . C9 . H91 . 107.377 no C10 . C9 . H91 . 106.919 no C11 . C9 . H91 . 105.688 no C9 . C10 . H101 . 109.828 no C9 . C10 . H102 . 109.373 no H101 . C10 . H102 . 109.428 no C9 . C10 . H103 . 109.688 no H101 . C10 . H103 . 109.210 no H102 . C10 . H103 . 109.300 no C9 . C11 . H111 . 112.164 no C9 . C11 . H112 . 111.039 no H111 . C11 . H112 . 108.738 no C9 . C11 . H113 . 110.834 no H111 . C11 . H113 . 107.295 no H112 . C11 . H113 . 106.536 no N3 . C12 . C13 . 116.7(3) yes N3 . C12 . H121 . 108.430 no C13 . C12 . H121 . 107.904 no N3 . C12 . H122 . 108.005 no C13 . C12 . H122 . 108.037 no H121 . C12 . H122 . 107.372 no C12 . C13 . C14 . 123.1(3) yes C12 . C13 . C18 . 119.5(3) yes C14 . C13 . C18 . 117.4(3) yes C13 . C14 . C15 . 121.9(3) yes C13 . C14 . H141 . 117.450 no C15 . C14 . H141 . 120.619 no C14 . C15 . C16 . 119.8(3) yes C14 . C15 . H151 . 120.148 no C16 . C15 . H151 . 120.060 no C15 . C16 . C17 . 119.5(3) yes C15 . C16 . O19 . 115.5(3) yes C17 . C16 . O19 . 124.9(3) yes C16 . C17 . C18 . 120.0(3) yes C16 . C17 . H171 . 121.175 no C18 . C17 . H171 . 118.798 no C13 . C18 . C17 . 121.4(3) yes C13 . C18 . H181 . 118.097 no C17 . C18 . H181 . 120.460 no C16 . O19 . C20 . 116.3(3) yes O19 . C20 . H201 . 112.850 no O19 . C20 . H202 . 110.048 no H201 . C20 . H202 . 107.549 no O19 . C20 . H203 . 110.956 no H201 . C20 . H203 . 108.813 no H202 . C20 . H203 . 106.362 no C1 . C22 . C23 . 114.1(2) yes C1 . C22 . H221 . 108.663 no C23 . C22 . H221 . 109.629 no C1 . C22 . H222 . 107.368 no C23 . C22 . H222 . 108.096 no H221 . C22 . H222 . 108.880 no C22 . C23 . C24 . 126.9(3) yes C22 . C23 . C27 . 126.6(3) yes C24 . C23 . C27 . 106.4(3) yes C23 . C24 . C25 . 108.4(3) yes C23 . C24 . C38 . 131.8(3) yes C25 . C24 . C38 . 119.8(3) yes C24 . C25 . N26 . 106.7(3) yes C24 . C25 . C35 . 122.3(3) yes N26 . C25 . C35 . 131.0(4) yes C25 . N26 . C27 . 107.9(3) yes C25 . N26 . C28 . 130.8(3) yes C27 . N26 . C28 . 120.9(3) yes C23 . C27 . N26 . 110.5(3) yes C23 . C27 . H271 . 124.987 no N26 . C27 . H271 . 124.442 no N26 . C28 . O29 . 111.2(3) yes N26 . C28 . O34 . 121.9(3) yes O29 . C28 . O34 . 126.9(4) yes C28 . O29 . C30 . 120.6(3) yes O29 . C30 . C31 . 102.2(3) yes O29 . C30 . C32 . 109.3(3) yes C31 . C30 . C32 . 110.8(4) yes O29 . C30 . C33 . 109.9(4) yes C31 . C30 . C33 . 110.9(4) yes C32 . C30 . C33 . 113.2(4) yes C30 . C31 . H311 . 110.644 no C30 . C31 . H312 . 111.396 no H311 . C31 . H312 . 108.322 no C30 . C31 . H313 . 109.642 no H311 . C31 . H313 . 107.590 no H312 . C31 . H313 . 109.152 no C30 . C32 . H321 . 110.347 no C30 . C32 . H322 . 110.853 no H321 . C32 . H322 . 108.534 no C30 . C32 . H323 . 109.805 no H321 . C32 . H323 . 108.551 no H322 . C32 . H323 . 108.695 no C30 . C33 . H331 . 112.033 no C30 . C33 . H332 . 113.025 no H331 . C33 . H332 . 106.898 no C30 . C33 . H333 . 110.573 no H331 . C33 . H333 . 106.549 no H332 . C33 . H333 . 107.421 no C25 . C35 . C36 . 117.4(4) yes C25 . C35 . H351 . 119.985 no C36 . C35 . H351 . 122.603 no C35 . C36 . C37 . 121.4(3) yes C35 . C36 . H361 . 120.138 no C37 . C36 . H361 . 118.456 no C36 . C37 . C38 . 121.0(3) yes C36 . C37 . H371 . 119.736 no C38 . C37 . H371 . 119.294 no C24 . C38 . C37 . 118.2(4) yes C24 . C38 . H381 . 120.921 no C37 . C38 . H381 . 120.906 no C1 . C39 . H391 . 111.435 no C1 . C39 . H392 . 110.660 no H391 . C39 . H392 . 110.767 no C1 . C39 . H393 . 108.508 no H391 . C39 . H393 . 108.281 no H392 . C39 . H393 . 107.032 no H401 . O40 . H402 . 103.414 no H411 . O41 . H412 . 93.566 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