Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Stephen G. Davies' 'Mark E. Bunnage' 'Ann M. Chippindale' 'Richard M. Parkin' 'Andrew D. Smith' 'Jonathan M. Withey' _publ_contact_author_name 'Prof Stephen G Davies' _publ_contact_author_address ; Dyson Perrins Laboratory University of Oxford South Parks Road Oxford Oxford Oxon OX1 3QY UNITED KINGDOM ; _publ_contact_author_email STEVE.DAVIES@CHEM.OX.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Asymmetric Synthesis of (1R,2S,3R)-3-methylcispentacin and (1S,2S,3R)-3-methyltranspentacin by kinetic resolution of tert-butyl (±)-3-methylcyclopentene-1-carboxylate ; data_CRYSTALS_cif_b _database_code_CSD 213043 _audit_creation_date 02-11-05 _audit_creation_method CRYSTALS # tert-butyl(1RS,2SR,3RS)-3-methyl- #2-(N,N-dibenzylamino)-cyclopentane-1-carboxylate #compound 168 # #================================================================= #============ ## -----------------REFERENCES ----------------------## _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. Carruthers, J.R. and Watkin, D.J. (1979), Acta Cryst, A35, 698-699. Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W. (1996) CRYSTALS Issue 10. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. (1994), RC93, Chemical Crystallography Laboratory, Oxford, UK. ; #================================================================= #======== # Diffractometer details #================================================================= #======== _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ' Enraf-Nonius CAD4 ' _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction ; RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994) ; _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' #================================================================= #======== # General computing #================================================================= #======== _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' #================================================================= #======== _chemical_name_systematic # IUPAC name, in full ; tert-butyl(1RS,2SR,3RS)-3-methyl-2-(N,N-dibenzylamino)- cyclopentane-1-carboxylate ; _chemical_melting_point 'not measured' _refine_ls_matrix_type full _atom_sites_solution_primary Direct_Methods _atom_sites_solution_hydrogens Geometric _refine_ls_hydrogen_treatment noref #***************************************************************** _cell_length_a 11.289(1) _cell_angle_alpha 96.03(1) _cell_length_b 11.4013(8) _cell_angle_beta 95.87(1) _cell_length_c 19.344(4) _cell_angle_gamma 112.820(7) _cell_volume 2254.06 _symmetry_cell_setting 'Triclinic ' _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0170 0.0090 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 'N ' 0.0290 0.0180 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 ' 0.0470 0.0320 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 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C50 H66 N2 O4 ' _chemical_formula_moiety ' C50 H66 N2 O4 ' _chemical_compound_source ; ? ; _chemical_formula_weight 759.09 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13 _cell_measurement_theta_max 27 _cell_measurement_temperature 293 _cell_formula_units_Z 2 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.18 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_max 0.60 _exptl_crystal_density_diffrn 1.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 824.0 _exptl_absorpt_coefficient_mu 0.541 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_process_details '\y scan' _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 1.00 _diffrn_standards_interval_time 3600 _diffrn_standards_number 3 _diffrn_ambient_temperature 293 _diffrn_reflns_number 8364 _reflns_number_total 7981 _diffrn_reflns_av_R_equivalents 0.019 _reflns_number_gt 4360 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 72.00 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -14 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _reflns_threshold_expression >3sigma(I) _refine_diff_density_min -0.31 _refine_diff_density_max 0.27 _refine_ls_number_reflns 4360 _refine_ls_number_parameters 506 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.0669 _refine_ls_goodness_of_fit_ref 1.0356 _refine_ls_shift/su_max 0.016594 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Caruthers and Watkin, 1979 2.27, 1.51, 1.50 ; #crystal faded at high theta, relections after [1 0 15] omitted #from data set. Hence low completeness #Asymmetric unit contains two moeities of formula C25 H33 N O2 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method 2\q/\w loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type O1 -0.1750(1) 0.5445(1) 0.81551(8) 0.0556 1.0000 Uani O2 0.2555(1) -0.1025(1) 0.71995(7) 0.0509 1.0000 Uani O3 0.3761(2) 0.0889(1) 0.6906(1) 0.0678 1.0000 Uani O4 -0.3906(2) 0.4370(2) 0.8102(1) 0.0790 1.0000 Uani N3 0.2369(2) 0.1348(1) 0.85143(9) 0.0465 1.0000 Uani N4 -0.2742(2) 0.3813(1) 0.63870(9) 0.0497 1.0000 Uani C7 -0.3408(2) 0.4666(1) 0.6492(1) 0.0467 1.0000 Uani C8 0.3767(2) 0.1636(2) 0.8604(1) 0.0549 1.0000 Uani C9 0.1759(2) 0.1437(1) 0.7842(1) 0.0443 1.0000 Uani C10 0.0286(2) 0.0003(1) 0.8873(1) 0.0498 1.0000 Uani C11 -0.1332(2) 0.4516(2) 0.6411(1) 0.0535 1.0000 Uani C12 0.4425(2) 0.2062(2) 0.9356(1) 0.0536 1.0000 Uani C13 0.1604(2) 0.0476(1) 0.7156(1) 0.0482 1.0000 Uani C14 0.1645(2) 0.0148(2) 0.8778(1) 0.0530 1.0000 Uani C15 -0.1032(2) 0.5426(2) 0.5879(1) 0.0491 1.0000 Uani C16 -0.2986(2) 0.5065(2) 0.7861(1) 0.0523 1.0000 Uani C17 -0.1508(2) 0.4970(2) 0.5166(1) 0.0572 1.0000 Uani C18 -0.4899(2) 0.4025(2) 0.6353(1) 0.0550 1.0000 Uani C19 -0.3074(2) 0.5627(1) 0.7198(1) 0.0507 1.0000 Uani C20 -0.2785(2) 0.1632(2) 0.6461(1) 0.0584 1.0000 Uani C21 -0.3038(2) 0.2763(2) 0.6797(1) 0.0580 1.0000 Uani C22 0.4228(3) 0.2994(2) 0.9796(1) 0.0647 1.0000 Uani C23 -0.1218(2) 0.5797(2) 0.4678(1) 0.0639 1.0000 Uani C24 0.0099(2) 0.0962(2) 0.9295(1) 0.0640 1.0000 Uani C25 0.3772(3) -0.1632(2) 0.6347(1) 0.0814 1.0000 Uani C26 -0.1148(3) 0.0817(2) 0.9400(2) 0.0746 1.0000 Uani C27 -0.1363(3) 0.5121(2) 0.8840(1) 0.0656 1.0000 Uani C28 0.2778(2) 0.0172(2) 0.7077(1) 0.0482 1.0000 Uani C29 0.4736(3) -0.0892(2) 0.7634(2) 0.0736 1.0000 Uani C30 -0.0271(2) 0.6725(2) 0.6083(1) 0.0614 1.0000 Uani C31 0.5289(3) 0.1581(2) 0.9620(2) 0.0686 1.0000 Uani C32 0.4896(3) 0.3428(2) 1.0476(1) 0.0755 1.0000 Uani C33 -0.0784(3) -0.1092(2) 0.8577(1) 0.0659 1.0000 Uani C34 -0.2180(3) -0.0151(2) 0.6575(2) 0.0852 1.0000 Uani C35 -0.2466(3) -0.0530(2) 0.5861(2) 0.0868 1.0000 Uani C36 0.3512(2) -0.1599(2) 0.7104(1) 0.0596 1.0000 Uani C37 -0.0439(3) 0.7100(2) 0.4891(1) 0.0708 1.0000 Uani C38 0.0020(3) 0.7554(2) 0.5589(2) 0.0742 1.0000 Uani C39 -0.2328(2) 0.0945(2) 0.6879(2) 0.0711 1.0000 Uani C40 -0.5244(2) 0.5175(2) 0.6533(1) 0.0652 1.0000 Uani C41 -0.4213(3) 0.6064(2) 0.7137(1) 0.0656 1.0000 Uani C42 0.2291(2) 0.2771(2) 0.7612(1) 0.0568 1.0000 Uani C43 -0.2205(3) -0.0285(3) 0.9103(2) 0.0814 1.0000 Uani C44 -0.1967(4) 0.5600(3) 0.9412(1) 0.0914 1.0000 Uani C45 0.5955(4) 0.2014(3) 1.0297(2) 0.0794 1.0000 Uani C46 -0.5457(3) 0.3305(2) 0.5611(2) 0.0794 1.0000 Uani C47 -0.3074(3) 0.1232(2) 0.5736(1) 0.0755 1.0000 Uani C48 0.2174(4) 0.3805(2) 0.8121(2) 0.0838 1.0000 Uani C49 0.1505(3) 0.2518(2) 0.6891(1) 0.0644 1.0000 Uani C50 0.1350(3) 0.1190(2) 0.6555(1) 0.0617 1.0000 Uani C51 0.5767(4) 0.2949(3) 1.0723(2) 0.0818 1.0000 Uani C52 -0.2913(4) 0.0148(2) 0.5442(2) 0.0913 1.0000 Uani C53 0.0111(4) 0.5866(4) 0.8965(2) 0.1031 1.0000 Uani C54 0.2800(3) -0.2953(2) 0.7269(2) 0.0782 1.0000 Uani C55 -0.2025(3) -0.1235(2) 0.8693(2) 0.0802 1.0000 Uani C56 -0.1695(5) 0.3697(3) 0.8783(2) 0.0938 1.0000 Uani H71 -0.3005 0.5119 0.6106 0.0472 1.0000 Uiso H81 0.3885 0.0845 0.8414 0.0538 1.0000 Uiso H82 0.4197 0.2342 0.8329 0.0538 1.0000 Uiso H91 0.0928 0.1202 0.8041 0.0456 1.0000 Uiso H111 -0.0948 0.5022 0.6891 0.0505 1.0000 Uiso H112 -0.0942 0.3879 0.6309 0.0505 1.0000 Uiso H131 0.0918 -0.0401 0.7155 0.0498 1.0000 Uiso H141 0.2124 0.0151 0.9241 0.0500 1.0000 Uiso H142 0.1583 -0.0598 0.8433 0.0500 1.0000 Uiso H171 -0.2067 0.4037 0.5008 0.0505 1.0000 Uiso H181 -0.5286 0.3317 0.6632 0.0535 1.0000 Uiso H191 -0.2177 0.6326 0.7267 0.0511 1.0000 Uiso H211 -0.2482 0.3098 0.7270 0.0596 1.0000 Uiso H212 -0.3974 0.2446 0.6853 0.0596 1.0000 Uiso H221 0.3601 0.3356 0.9620 0.0538 1.0000 Uiso H231 -0.1564 0.5459 0.4167 0.0743 1.0000 Uiso H241 0.0863 0.1761 0.9522 0.0500 1.0000 Uiso H251 0.4422 -0.2021 0.6291 0.0913 1.0000 Uiso H252 0.4128 -0.0737 0.6236 0.0913 1.0000 Uiso H253 0.2945 -0.2166 0.6024 0.0913 1.0000 Uiso H261 -0.1270 0.1518 0.9696 0.0645 1.0000 Uiso H291 0.5370 -0.1290 0.7560 0.0781 1.0000 Uiso H292 0.4519 -0.0943 0.8119 0.0781 1.0000 Uiso H293 0.5132 0.0035 0.7567 0.0781 1.0000 Uiso H301 0.0075 0.7074 0.6593 0.0715 1.0000 Uiso H311 0.5434 0.0901 0.9316 0.0895 1.0000 Uiso H321 0.4741 0.4087 1.0788 0.0648 1.0000 Uiso H331 -0.0670 -0.1793 0.8272 0.0763 1.0000 Uiso H341 -0.1860 -0.0656 0.6880 0.0738 1.0000 Uiso H351 -0.2356 -0.1315 0.5646 0.0909 1.0000 Uiso H371 -0.0217 0.7696 0.4537 0.0660 1.0000 Uiso H381 0.0571 0.8489 0.5744 0.0599 1.0000 Uiso H391 -0.2101 0.1229 0.7400 0.0909 1.0000 Uiso H401 -0.6126 0.4881 0.6677 0.0535 1.0000 Uiso H402 -0.5235 0.5626 0.6116 0.0535 1.0000 Uiso H411 -0.4594 0.6009 0.7584 0.0511 1.0000 Uiso H412 -0.3901 0.6972 0.7041 0.0511 1.0000 Uiso H421 0.3250 0.3133 0.7605 0.0587 1.0000 Uiso H431 -0.3094 -0.0395 0.9186 0.0828 1.0000 Uiso H441 -0.1683 0.5375 0.9872 0.0992 1.0000 Uiso H442 -0.1649 0.6561 0.9457 0.0992 1.0000 Uiso H443 -0.2926 0.5194 0.9294 0.0992 1.0000 Uiso H451 0.6582 0.1650 1.0476 0.0739 1.0000 Uiso H461 -0.6425 0.2913 0.5556 0.0791 1.0000 Uiso H462 -0.5173 0.3923 0.5267 0.0791 1.0000 Uiso H463 -0.5128 0.2615 0.5518 0.0791 1.0000 Uiso H471 -0.3408 0.1722 0.5427 0.0952 1.0000 Uiso H481 0.2535 0.4647 0.7943 0.0880 1.0000 Uiso H482 0.2668 0.3879 0.8594 0.0880 1.0000 Uiso H483 0.1235 0.3575 0.8160 0.0880 1.0000 Uiso H491 0.0635 0.2529 0.6931 0.0661 1.0000 Uiso H492 0.1976 0.3178 0.6604 0.0661 1.0000 Uiso H501 0.0442 0.0700 0.6293 0.0498 1.0000 Uiso H502 0.1985 0.1269 0.6221 0.0498 1.0000 Uiso H511 0.6267 0.3274 1.1209 0.0895 1.0000 Uiso H521 -0.3122 -0.0134 0.4924 0.0781 1.0000 Uiso H531 0.0487 0.5719 0.9421 0.1090 1.0000 Uiso H532 0.0322 0.6809 0.8983 0.1090 1.0000 Uiso H533 0.0489 0.5569 0.8573 0.1090 1.0000 Uiso H541 0.3359 -0.3446 0.7219 0.0868 1.0000 Uiso H542 0.2598 -0.2901 0.7757 0.0868 1.0000 Uiso H543 0.1969 -0.3404 0.6927 0.0868 1.0000 Uiso H551 -0.2795 -0.2040 0.8473 0.0637 1.0000 Uiso H561 -0.1429 0.3494 0.9247 0.1036 1.0000 Uiso H562 -0.2659 0.3208 0.8635 0.1036 1.0000 Uiso H563 -0.1231 0.3437 0.8422 0.1036 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 O1 0.056(1) 0.0605(7) 0.053(1) 0.0079(6) 0.001(1) 0.0265(7) O2 0.0506(8) 0.0466(5) 0.0594(8) 0.0090(6) 0.0086(9) 0.0222(5) O3 0.0598(9) 0.0598(7) 0.096(1) 0.0231(8) 0.028(1) 0.0199(7) O4 0.068(1) 0.091(1) 0.078(1) 0.0219(9) 0.023(1) 0.0143(9) N3 0.044(1) 0.0468(6) 0.0491(9) 0.0114(6) 0.004(1) 0.0169(6) N4 0.0480(9) 0.0463(6) 0.057(1) 0.0088(7) 0.013(1) 0.0192(6) C7 0.043(1) 0.0456(7) 0.049(1) 0.0038(8) 0.005(1) 0.0159(7) C8 0.047(1) 0.066(1) 0.054(1) 0.0073(9) 0.003(1) 0.0242(9) C9 0.043(1) 0.0423(7) 0.050(1) 0.0121(7) 0.005(1) 0.0179(7) C10 0.056(1) 0.0453(7) 0.049(1) 0.0133(7) 0.009(1) 0.0168(8) C11 0.049(1) 0.0576(9) 0.056(1) 0.0096(9) 0.009(1) 0.0227(9) C12 0.048(1) 0.0530(9) 0.057(1) 0.0111(9) 0.001(1) 0.0164(8) C13 0.044(1) 0.0463(8) 0.055(1) 0.0087(8) 0.002(1) 0.0186(7) C14 0.058(1) 0.0487(8) 0.057(1) 0.0165(8) 0.010(1) 0.0222(8) C15 0.042(1) 0.0524(8) 0.055(1) 0.0077(8) 0.009(1) 0.0195(8) C16 0.051(1) 0.0492(8) 0.055(1) 0.0005(8) 0.007(1) 0.0190(8) C17 0.055(1) 0.0558(9) 0.057(1) 0.0025(9) 0.006(2) 0.0193(9) C18 0.044(1) 0.0541(9) 0.062(1) 0.0019(9) 0.003(1) 0.0154(9) C19 0.048(1) 0.0443(7) 0.059(1) 0.0014(8) -0.000(1) 0.0183(8) C20 0.056(1) 0.0463(8) 0.080(2) 0.010(1) 0.020(2) 0.0197(8) C21 0.073(1) 0.0486(8) 0.066(1) 0.0147(8) 0.022(1) 0.0283(9) C22 0.068(2) 0.068(1) 0.059(1) 0.003(1) -0.002(2) 0.030(1) C23 0.064(1) 0.077(1) 0.054(1) 0.011(1) 0.004(2) 0.029(1) C24 0.071(1) 0.0499(8) 0.073(2) 0.0059(9) 0.022(2) 0.0181(9) C25 0.100(2) 0.094(1) 0.076(2) -0.004(1) 0.022(2) 0.054(2) C26 0.088(2) 0.074(1) 0.083(2) 0.019(1) 0.034(2) 0.041(1) C27 0.086(2) 0.077(1) 0.052(1) 0.008(1) -0.004(2) 0.046(1) C28 0.050(1) 0.0458(7) 0.048(1) 0.0070(8) 0.006(1) 0.0186(8) C29 0.065(2) 0.079(1) 0.088(2) -0.001(1) 0.002(2) 0.038(1) C30 0.059(1) 0.0556(9) 0.062(1) 0.0016(9) 0.002(2) 0.0142(9) C31 0.077(2) 0.070(1) 0.073(2) 0.007(1) -0.011(2) 0.040(1) C32 0.087(2) 0.072(1) 0.064(2) 0.000(1) -0.003(2) 0.028(1) C33 0.067(2) 0.0531(9) 0.069(2) -0.001(1) 0.006(2) 0.013(1) C34 0.077(2) 0.065(1) 0.155(4) 0.014(2) 0.009(3) 0.041(1) C35 0.090(2) 0.061(1) 0.142(3) -0.013(2) 0.016(3) 0.038(1) C36 0.066(1) 0.0596(9) 0.066(1) 0.006(1) 0.013(2) 0.035(1) C37 0.072(2) 0.070(1) 0.075(2) 0.027(1) 0.010(2) 0.025(1) C38 0.079(2) 0.054(1) 0.085(2) 0.014(1) 0.007(2) 0.012(1) C39 0.061(1) 0.060(1) 0.103(2) 0.011(1) 0.012(2) 0.027(1) C40 0.055(1) 0.067(1) 0.081(2) 0.002(1) 0.004(2) 0.031(1) C41 0.074(2) 0.070(1) 0.075(2) -0.006(1) -0.010(2) 0.046(1) C42 0.065(1) 0.0444(8) 0.067(1) 0.0197(9) 0.007(2) 0.0191(9) C43 0.065(2) 0.094(2) 0.094(2) 0.026(2) 0.023(2) 0.030(1) C44 0.149(3) 0.120(2) 0.056(1) 0.004(1) 0.016(2) 0.081(2) C45 0.091(3) 0.087(2) 0.087(2) 0.014(2) -0.030(3) 0.044(2) C46 0.069(2) 0.085(1) 0.079(2) -0.016(1) -0.004(2) 0.023(1) C47 0.093(2) 0.058(1) 0.084(2) 0.001(1) 0.024(2) 0.029(1) C48 0.141(3) 0.054(1) 0.091(2) 0.012(1) 0.007(3) 0.047(2) C49 0.075(2) 0.059(1) 0.072(1) 0.027(1) 0.001(2) 0.028(1) C50 0.070(2) 0.075(1) 0.053(1) 0.011(1) -0.010(2) 0.034(1) C51 0.100(3) 0.075(1) 0.064(2) 0.005(1) -0.016(2) 0.015(2) C52 0.111(2) 0.064(1) 0.121(3) -0.014(2) 0.035(3) 0.031(1) C53 0.097(3) 0.130(3) 0.100(3) 0.013(2) -0.020(4) 0.053(2) C54 0.087(2) 0.058(1) 0.115(2) 0.015(1) 0.014(2) 0.040(1) C55 0.055(2) 0.079(1) 0.097(2) 0.003(1) 0.001(2) 0.009(1) C56 0.157(4) 0.084(2) 0.081(2) 0.018(1) 0.003(3) 0.066(2) _refine_ls_extinction_coef 235.5(355) _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 O1 . C16 . 1.332(3) yes O1 . C27 . 1.481(3) yes O2 . C28 . 1.340(2) yes O2 . C36 . 1.480(2) yes O3 . C28 . 1.198(2) yes O4 . C16 . 1.209(2) yes N3 . C8 . 1.469(3) yes N3 . C9 . 1.440(3) yes N3 . C14 . 1.471(2) yes N4 . C7 . 1.453(2) yes N4 . C11 . 1.471(2) yes N4 . C21 . 1.455(2) yes C7 . C18 . 1.533(3) yes C7 . C19 . 1.571(2) yes C7 . H71 . 1.000 no C8 . C12 . 1.501(3) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no C9 . C13 . 1.578(2) yes C9 . C42 . 1.536(2) yes C9 . H91 . 1.000 no C10 . C14 . 1.510(3) yes C10 . C24 . 1.390(2) yes C10 . C33 . 1.373(3) yes C11 . C15 . 1.509(3) yes C11 . H111 . 1.000 no C11 . H112 . 1.000 no C12 . C22 . 1.392(3) yes C12 . C31 . 1.373(4) yes C13 . C28 . 1.512(3) yes C13 . C50 . 1.553(3) yes C13 . H131 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C15 . C17 . 1.393(3) yes C15 . C30 . 1.381(2) yes C16 . C19 . 1.505(3) yes C17 . C23 . 1.378(3) yes C17 . H171 . 1.000 no C18 . C40 . 1.522(3) yes C18 . C46 . 1.516(3) yes C18 . H181 . 1.000 no C19 . C41 . 1.547(3) yes C19 . H191 . 1.000 no C20 . C21 . 1.521(2) yes C20 . C39 . 1.376(4) yes C20 . C47 . 1.392(4) yes C21 . H211 . 1.000 no C21 . H212 . 1.000 no C22 . C32 . 1.384(4) yes C22 . H221 . 1.000 no C23 . C37 . 1.391(3) yes C23 . H231 . 1.000 no C24 . C26 . 1.391(3) yes C24 . H241 . 1.000 no C25 . C36 . 1.522(3) yes C25 . H251 . 1.000 no C25 . H252 . 1.000 no C25 . H253 . 1.000 no C26 . C43 . 1.370(4) yes C26 . H261 . 1.000 no C27 . C44 . 1.517(3) yes C27 . C53 . 1.525(5) yes C27 . C56 . 1.506(3) yes C29 . C36 . 1.511(4) yes C29 . H291 . 1.000 no C29 . H292 . 1.000 no C29 . H293 . 1.000 no C30 . C38 . 1.389(3) yes C30 . H301 . 1.000 no C31 . C45 . 1.378(5) yes C31 . H311 . 1.000 no C32 . C51 . 1.367(5) yes C32 . H321 . 1.000 no C33 . C55 . 1.391(4) yes C33 . H331 . 1.000 no C34 . C35 . 1.369(6) yes C34 . C39 . 1.402(3) yes C34 . H341 . 1.000 no C35 . C52 . 1.364(6) yes C35 . H351 . 1.000 no C36 . C54 . 1.525(3) yes C37 . C38 . 1.364(4) yes C37 . H371 . 1.000 no C38 . H381 . 1.000 no C39 . H391 . 1.000 no C40 . C41 . 1.519(4) yes C40 . H401 . 1.000 no C40 . H402 . 1.000 no C41 . H411 . 1.000 no C41 . H412 . 1.000 no C42 . C48 . 1.510(3) yes C42 . C49 . 1.511(4) yes C42 . H421 . 1.000 no C43 . C55 . 1.365(4) yes C43 . H431 . 1.000 no C44 . H441 . 1.000 no C44 . H442 . 1.000 no C44 . H443 . 0.990 no C45 . C51 . 1.373(4) yes C45 . H451 . 1.000 no C46 . H461 . 1.000 no C46 . H462 . 1.000 no C46 . H463 . 1.000 no C47 . C52 . 1.391(3) yes C47 . H471 . 1.000 no C48 . H481 . 1.000 no C48 . H482 . 1.000 no C48 . H483 . 1.000 no C49 . C50 . 1.519(3) yes C49 . H491 . 1.000 no C49 . H492 . 1.000 no C50 . H501 . 1.000 no C50 . H502 . 1.000 no C51 . H511 . 1.000 no C52 . H521 . 1.000 no C53 . H531 . 1.000 no C53 . H532 . 1.000 no C53 . H533 . 1.000 no C54 . H541 . 1.000 no C54 . H542 . 1.000 no C54 . H543 . 1.000 no C55 . H551 . 1.000 no C56 . H561 . 1.000 no C56 . H562 . 1.000 no C56 . H563 . 1.000 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 C16 . O1 . C27 . 123.1(2) no C28 . O2 . C36 . 121.8(1) no C8 . N3 . C9 . 117.9(1) no C8 . N3 . C14 . 110.9(2) no C9 . N3 . C14 . 113.3(2) no C7 . N4 . C11 . 112.8(1) no C7 . N4 . C21 . 117.1(1) no C11 . N4 . C21 . 111.9(2) no N4 . C7 . C18 . 116.1(1) no N4 . C7 . C19 . 120.9(2) no C18 . C7 . C19 . 104.4(1) no N4 . C7 . H71 . 89.45 no C18 . C7 . H71 . 114.47 no C19 . C7 . H71 . 111.44 no N3 . C8 . C12 . 113.7(1) no N3 . C8 . H81 . 108.72 no C12 . C8 . H81 . 108.42 no N3 . C8 . H82 . 108.37 no C12 . C8 . H82 . 108.31 no H81 . C8 . H82 . 109.29 no N3 . C9 . C13 . 121.7(1) no N3 . C9 . C42 . 115.8(2) no C13 . C9 . C42 . 104.0(1) no N3 . C9 . H91 . 87.82 no C13 . C9 . H91 . 111.69 no C42 . C9 . H91 . 115.71 no C14 . C10 . C24 . 120.2(2) no C14 . C10 . C33 . 121.4(2) no C24 . C10 . C33 . 118.3(2) no N4 . C11 . C15 . 111.8(2) no N4 . C11 . H111 . 108.70 no C15 . C11 . H111 . 108.88 no N4 . C11 . H112 . 108.71 no C15 . C11 . H112 . 108.88 no H111 . C11 . H112 . 109.86 no C8 . C12 . C22 . 121.4(2) no C8 . C12 . C31 . 120.7(2) no C22 . C12 . C31 . 117.9(2) no C9 . C13 . C28 . 114.8(2) no C9 . C13 . C50 . 103.1(1) no C28 . C13 . C50 . 110.4(1) no C9 . C13 . H131 . 112.05 no C28 . C13 . H131 . 101.36 no C50 . C13 . H131 . 115.62 no N3 . C14 . C10 . 112.2(2) no N3 . C14 . H141 . 108.84 no C10 . C14 . H141 . 108.71 no N3 . C14 . H142 . 108.69 no C10 . C14 . H142 . 108.69 no H141 . C14 . H142 . 109.69 no C11 . C15 . C17 . 120.5(2) no C11 . C15 . C30 . 121.1(2) no C17 . C15 . C30 . 118.4(2) no O1 . C16 . O4 . 124.1(2) no O1 . C16 . C19 . 110.8(1) no O4 . C16 . C19 . 125.1(2) no C15 . C17 . C23 . 120.6(2) no C15 . C17 . H171 . 119.67 no C23 . C17 . H171 . 119.72 no C7 . C18 . C40 . 101.4(1) no C7 . C18 . C46 . 113.7(2) no C40 . C18 . C46 . 114.1(2) no C7 . C18 . H181 . 114.21 no C40 . C18 . H181 . 113.52 no C46 . C18 . H181 . 100.56 no C7 . C19 . C16 . 115.6(1) no C7 . C19 . C41 . 101.9(2) no C16 . C19 . C41 . 111.2(2) no C7 . C19 . H191 . 112.99 no C16 . C19 . H191 . 99.58 no C41 . C19 . H191 . 116.30 no C21 . C20 . C39 . 119.9(2) no C21 . C20 . C47 . 121.0(2) no C39 . C20 . C47 . 119.0(2) no N4 . C21 . C20 . 113.4(1) no N4 . C21 . H211 . 108.56 no C20 . C21 . H211 . 108.05 no N4 . C21 . H212 . 108.79 no C20 . C21 . H212 . 108.37 no H211 . C21 . H212 . 109.65 no C12 . C22 . C32 . 120.7(3) no C12 . C22 . H221 . 119.76 no C32 . C22 . H221 . 119.54 no C17 . C23 . C37 . 120.3(2) no C17 . C23 . H231 . 119.95 no C37 . C23 . H231 . 119.73 no C10 . C24 . C26 . 120.4(2) no C10 . C24 . H241 . 119.83 no C26 . C24 . H241 . 119.78 no C36 . C25 . H251 . 108.98 no C36 . C25 . H252 . 109.49 no H251 . C25 . H252 . 109.48 no C36 . C25 . H253 . 109.34 no H251 . C25 . H253 . 109.54 no H252 . C25 . H253 . 109.98 no C24 . C26 . C43 . 120.5(2) no C24 . C26 . H261 . 119.59 no C43 . C26 . H261 . 119.92 no O1 . C27 . C44 . 110.4(2) no O1 . C27 . C53 . 102.3(2) no C44 . C27 . C53 . 110.7(3) no O1 . C27 . C56 . 110.7(2) no C44 . C27 . C56 . 112.4(2) no C53 . C27 . C56 . 109.8(3) no O2 . C28 . O3 . 124.5(2) no O2 . C28 . C13 . 110.9(1) no O3 . C28 . C13 . 124.6(2) no C36 . C29 . H291 . 109.43 no C36 . C29 . H292 . 109.58 no H291 . C29 . H292 . 109.91 no C36 . C29 . H293 . 109.22 no H291 . C29 . H293 . 109.21 no H292 . C29 . H293 . 109.47 no C15 . C30 . C38 . 120.8(2) no C15 . C30 . H301 . 119.68 no C38 . C30 . H301 . 119.54 no C12 . C31 . C45 . 121.4(2) no C12 . C31 . H311 . 119.30 no C45 . C31 . H311 . 119.38 no C22 . C32 . C51 . 120.2(2) no C22 . C32 . H321 . 120.08 no C51 . C32 . H321 . 119.69 no C10 . C33 . C55 . 120.8(2) no C10 . C33 . H331 . 119.57 no C55 . C33 . H331 . 119.62 no C35 . C34 . C39 . 120.2(3) no C35 . C34 . H341 . 119.82 no C39 . C34 . H341 . 119.93 no C34 . C35 . C52 . 120.2(2) no C34 . C35 . H351 . 119.89 no C52 . C35 . H351 . 119.94 no O2 . C36 . C25 . 110.0(2) no O2 . C36 . C29 . 110.6(1) no C25 . C36 . C29 . 112.9(2) no O2 . C36 . C54 . 102.0(1) no C25 . C36 . C54 . 111.4(2) no C29 . C36 . C54 . 109.5(2) no C23 . C37 . C38 . 119.3(2) no C23 . C37 . H371 . 120.32 no C38 . C37 . H371 . 120.35 no C30 . C38 . C37 . 120.6(2) no C30 . C38 . H381 . 119.88 no C37 . C38 . H381 . 119.54 no C20 . C39 . C34 . 120.0(3) no C20 . C39 . H391 . 119.96 no C34 . C39 . H391 . 120.00 no C18 . C40 . C41 . 106.4(2) no C18 . C40 . H401 . 110.03 no C41 . C40 . H401 . 110.57 no C18 . C40 . H402 . 110.03 no C41 . C40 . H402 . 110.35 no H401 . C40 . H402 . 109.47 no C19 . C41 . C40 . 108.0(1) no C19 . C41 . H411 . 110.16 no C40 . C41 . H411 . 109.50 no C19 . C41 . H412 . 110.23 no C40 . C41 . H412 . 109.58 no H411 . C41 . H412 . 109.24 no C9 . C42 . C48 . 113.1(2) no C9 . C42 . C49 . 102.3(2) no C48 . C42 . C49 . 114.1(2) no C9 . C42 . H421 . 113.83 no C48 . C42 . H421 . 101.22 no C49 . C42 . H421 . 112.77 no C26 . C43 . C55 . 119.3(2) no C26 . C43 . H431 . 120.43 no C55 . C43 . H431 . 120.24 no C27 . C44 . H441 . 108.89 no C27 . C44 . H442 . 109.05 no H441 . C44 . H442 . 108.76 no C27 . C44 . H443 . 110.00 no H441 . C44 . H443 . 109.88 no H442 . C44 . H443 . 110.23 no C31 . C45 . C51 . 120.2(4) no C31 . C45 . H451 . 119.74 no C51 . C45 . H451 . 120.09 no C18 . C46 . H461 . 109.62 no C18 . C46 . H462 . 109.25 no H461 . C46 . H462 . 109.53 no C18 . C46 . H463 . 109.46 no H461 . C46 . H463 . 109.80 no H462 . C46 . H463 . 109.16 no C20 . C47 . C52 . 120.3(3) no C20 . C47 . H471 . 119.74 no C52 . C47 . H471 . 119.98 no C42 . C48 . H481 . 109.30 no C42 . C48 . H482 . 109.77 no H481 . C48 . H482 . 109.61 no C42 . C48 . H483 . 109.38 no H481 . C48 . H483 . 109.30 no H482 . C48 . H483 . 109.46 no C42 . C49 . C50 . 106.0(2) no C42 . C49 . H491 . 110.41 no C50 . C49 . H491 . 110.22 no C42 . C49 . H492 . 110.31 no C50 . C49 . H492 . 110.05 no H491 . C49 . H492 . 109.79 no C13 . C50 . C49 . 107.5(2) no C13 . C50 . H501 . 109.80 no C49 . C50 . H501 . 109.86 no C13 . C50 . H502 . 110.21 no C49 . C50 . H502 . 110.23 no H501 . C50 . H502 . 109.22 no C32 . C51 . C45 . 119.6(3) no C32 . C51 . H511 . 120.55 no C45 . C51 . H511 . 119.86 no C35 . C52 . C47 . 120.2(3) no C35 . C52 . H521 . 119.78 no C47 . C52 . H521 . 119.94 no C27 . C53 . H531 . 109.59 no C27 . C53 . H532 . 109.21 no H531 . C53 . H532 . 109.37 no C27 . C53 . H533 . 109.64 no H531 . C53 . H533 . 109.66 no H532 . C53 . H533 . 109.35 no C36 . C54 . H541 . 109.42 no C36 . C54 . H542 . 109.70 no H541 . C54 . H542 . 109.97 no C36 . C54 . H543 . 109.09 no H541 . C54 . H543 . 109.09 no H542 . C54 . H543 . 109.57 no C33 . C55 . C43 . 120.6(2) no C33 . C55 . H551 . 119.78 no C43 . C55 . H551 . 119.60 no C27 . C56 . H561 . 109.78 no C27 . C56 . H562 . 109.28 no H561 . C56 . H562 . 109.45 no C27 . C56 . H563 . 109.58 no H561 . C56 . H563 . 109.64 no H562 . C56 . H563 . 109.09 no data_CRYSTALS_cif _database_code_CSD 213044 _audit_creation_date 02-11-05 _audit_creation_method CRYSTALS #tert-butyl(1R,2S,3R,aS)-3-methyl-2-(N-benzyl)-N-a- #methylbenzylaminocyclopentane-1-carboxylate ## -----------------REFERENCES ----------------------## _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. Carruthers, J.R. and Watkin, D.J. (1979), Acta Cryst, A35, 698-699. Larsen, A. C. (1967), Acta Cryst. 23, 440-449. North, A.C.T., Phillips, D.C. and Mathews, F.S., (1968), Acta Cryst, A24, 351-359. Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W. (1996) CRYSTALS Issue 10. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. (1994), RC93, Chemical Crystallography Laboratory, Oxford, UK. ; #============================================================ #============= # Diffractometer details #============================================================ #============= _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ' Enraf-Nonius CAD4 ' _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction ; RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994) ; _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' #============================================================ #============= # General computing #============================================================ #============= _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' #============================================================ #============= _chemical_name_systematic # IUPAC name, in full ; tert-butyl(1R,2S,3R,aS)-3-methyl-2-(N-benzylamino)- cyclopentane-1-carboxylate ; _chemical_melting_point 'not measured' _refine_ls_matrix_type full _atom_sites_solution_primary Direct_Methods _atom_sites_solution_hydrogens Geometric _refine_ls_hydrogen_treatment noref #************************************************************ _cell_length_a 9.9698(8) _cell_angle_alpha 90 _cell_length_b 10.8697(9) _cell_angle_beta 90 _cell_length_c 21.974(4) _cell_angle_gamma 90 _cell_volume 2381.28 _symmetry_cell_setting 'Orthorhombic ' _symmetry_space_group_name_H-M 'P 21 2 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ac' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y,-z+1/2 -x,y,-z -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 ' 0.0170 0.0090 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 'N ' 0.0290 0.0180 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 ' 0.0470 0.0320 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 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C26 H35 N1 O2 ' _chemical_formula_moiety ' C26 H35 N1 O2 ' _chemical_compound_source ; see paper ; _chemical_formula_weight 393.55 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 28 _cell_measurement_temperature 293 _cell_formula_units_Z 4.00 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.17 _exptl_crystal_size_mid 0.80 _exptl_crystal_size_max 1.00 _exptl_crystal_density_diffrn 1.098 _exptl_crystal_density_meas ? _exptl_crystal_F_000 856.00 _exptl_absorpt_coefficient_mu 0.528 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_process_details '\y scan' _exptl_absorpt_correction_T_min 0.632 _exptl_absorpt_correction_T_max 0.914 _diffrn_standards_interval_time 3600 _diffrn_standards_interval_count ? _diffrn_standards_number 3 _diffrn_standards_decay_% 2.92 _diffrn_ambient_temperature 293 _diffrn_reflns_number 6749 _reflns_number_total 4600 _diffrn_reflns_av_R_equivalents 0.018 _reflns_number_gt 4273 # number of reflections with Friedals Law is 4600 # number of reflections without Friedals Law is 0 #Theoretical number of reflections is about 2671 _diffrn_measured_fraction_theta_max 0.95 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 72.00 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 27 _reflns_threshold_expression >3.00\s(I) _refine_diff_density_min -0.263 _refine_diff_density_max 0.269 _refine_ls_number_reflns 4273 _refine_ls_number_parameters 264 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.0508 _refine_ls_goodness_of_fit_ref 1.0059 _refine_ls_shift/su_max 0.018190 _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_abs_structure_details 'Flack, 1929 Friedal pairs' _chemical_absolute_configuration ad _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers and Watkin, 1979) 2.27, 1.51, 1.50 ; _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method 2\q/\w loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type O1 0.3339(1) 0.06520(9) 0.09638(5) 0.0570 1.0000 Uani O2 0.5116(1) -0.0065(1) 0.14781(6) 0.0707 1.0000 Uani N3 0.5057(1) 0.3162(1) 0.20022(5) 0.0504 1.0000 Uani C4 0.5241(1) 0.1906(1) 0.09788(6) 0.0485 1.0000 Uani C5 0.4302(1) 0.2216(1) 0.23247(6) 0.0539 1.0000 Uani C6 0.4579(1) 0.0729(1) 0.11859(6) 0.0494 1.0000 Uani C7 0.3986(2) 0.2536(1) 0.29831(6) 0.0537 1.0000 Uani C8 0.4791(2) 0.3280(2) 0.33318(7) 0.0669 1.0000 Uani C9 0.5858(1) 0.2735(1) 0.14870(6) 0.0488 1.0000 Uani C10 0.4334(2) 0.4336(1) 0.19148(7) 0.0593 1.0000 Uani C11 0.2608(2) 0.2189(2) 0.38733(8) 0.0764 1.0000 Uani C12 0.3456(2) 0.4354(1) 0.13451(7) 0.0585 1.0000 Uani C13 0.2873(2) 0.1994(2) 0.32577(8) 0.0673 1.0000 Uani C14 0.2233(2) 0.3750(2) 0.1343(1) 0.0752 1.0000 Uani C15 0.3858(2) 0.4914(2) 0.08076(9) 0.0756 1.0000 Uani C16 0.2490(2) -0.0440(2) 0.10690(8) 0.0684 1.0000 Uani C17 0.1909(3) 0.4207(3) 0.0289(1) 0.0926 1.0000 Uani C18 0.5302(3) 0.5410(2) 0.1953(1) 0.0801 1.0000 Uani C19 0.4525(3) 0.3464(2) 0.39445(8) 0.0773 1.0000 Uani C20 0.6502(2) 0.1565(2) 0.06111(7) 0.0637 1.0000 Uani C21 0.3132(3) -0.1568(2) 0.0817(1) 0.0962 1.0000 Uani C22 0.3084(3) 0.4834(3) 0.02869(9) 0.0867 1.0000 Uani C23 0.3445(2) 0.2920(2) 0.42089(8) 0.0760 1.0000 Uani C24 0.7165(1) 0.2082(2) 0.16626(7) 0.0613 1.0000 Uani C25 0.8152(2) 0.2918(3) 0.1985(1) 0.0914 1.0000 Uani C26 0.1472(2) 0.3660(2) 0.0816(1) 0.0939 1.0000 Uani C27 0.2194(4) -0.0548(3) 0.1736(1) 0.1049 1.0000 Uani C28 0.7673(2) 0.1566(2) 0.10526(9) 0.0738 1.0000 Uani C29 0.1254(2) -0.0154(3) 0.0693(2) 0.1111 1.0000 Uani H41 0.4489 0.2333 0.0764 0.0485 1.0000 Uiso H51 0.4839 0.1439 0.2320 0.0544 1.0000 Uiso H52 0.3437 0.2081 0.2105 0.0544 1.0000 Uiso H81 0.5581 0.3695 0.3141 0.0785 1.0000 Uiso H91 0.5949 0.3600 0.1337 0.0491 1.0000 Uiso H101 0.3694 0.4402 0.2264 0.0606 1.0000 Uiso H111 0.1809 0.1796 0.4069 0.0677 1.0000 Uiso H131 0.2260 0.1462 0.3012 0.0805 1.0000 Uiso H141 0.1893 0.3373 0.1729 0.0964 1.0000 Uiso H151 0.4720 0.5383 0.0797 0.0614 1.0000 Uiso H171 0.1363 0.4144 -0.0092 0.0964 1.0000 Uiso H181 0.4802 0.6197 0.1893 0.0817 1.0000 Uiso H182 0.5744 0.5414 0.2361 0.0817 1.0000 Uiso H183 0.6001 0.5325 0.1629 0.0817 1.0000 Uiso H191 0.5130 0.3999 0.4193 0.0673 1.0000 Uiso H201 0.6657 0.2184 0.0282 0.0485 1.0000 Uiso H202 0.6393 0.0730 0.0426 0.0485 1.0000 Uiso H211 0.2540 -0.2295 0.0893 0.1010 1.0000 Uiso H212 0.4019 -0.1702 0.1018 0.1010 1.0000 Uiso H213 0.3267 -0.1467 0.0368 0.1010 1.0000 Uiso H221 0.3396 0.5242 -0.0096 0.0797 1.0000 Uiso H231 0.3262 0.3056 0.4651 0.0805 1.0000 Uiso H241 0.7037 0.1424 0.1976 0.0617 1.0000 Uiso H251 0.8981 0.2444 0.2088 0.0957 1.0000 Uiso H252 0.8390 0.3622 0.1713 0.0957 1.0000 Uiso H253 0.7736 0.3239 0.2368 0.0957 1.0000 Uiso H261 0.0605 0.3198 0.0820 0.0772 1.0000 Uiso H271 0.1620 -0.1287 0.1810 0.1306 1.0000 Uiso H272 0.3055 -0.0636 0.1967 0.1306 1.0000 Uiso H273 0.1713 0.0206 0.1878 0.1306 1.0000 Uiso H281 0.8412 0.2095 0.0891 0.0617 1.0000 Uiso H282 0.8011 0.0708 0.1110 0.0617 1.0000 Uiso H291 0.0597 -0.0844 0.0731 0.1180 1.0000 Uiso H292 0.0835 0.0625 0.0844 0.1180 1.0000 Uiso H293 0.1516 -0.0052 0.0257 0.1180 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 O1 0.0531(5) 0.0585(5) 0.0609(6) 0.0045(4) -0.0032(4) -0.0066(4) O2 0.0845(8) 0.0555(6) 0.0822(7) 0.0097(5) -0.0211(6) -0.0019(5) N3 0.0619(6) 0.0475(5) 0.0447(5) -0.0024(4) 0.0080(5) -0.0019(5) C4 0.0522(6) 0.0524(6) 0.0418(5) -0.0011(5) 0.0008(5) -0.0003(5) C5 0.0643(8) 0.0515(7) 0.0479(6) -0.0037(5) 0.0030(6) -0.0035(6) C6 0.0555(7) 0.0487(6) 0.0448(6) -0.0008(5) -0.0017(5) 0.0012(5) C7 0.0701(8) 0.0502(6) 0.0456(7) -0.0013(5) 0.0052(6) 0.0090(6) C8 0.082(1) 0.0618(8) 0.0604(8) -0.0040(7) 0.0037(8) -0.0078(8) C9 0.0545(7) 0.0485(6) 0.0448(6) -0.0025(5) 0.0043(5) -0.0044(5) C10 0.083(1) 0.0480(7) 0.0561(8) -0.0014(6) 0.0160(7) 0.0042(7) C11 0.097(1) 0.080(1) 0.067(1) 0.0040(9) 0.0302(9) -0.001(1) C12 0.0721(9) 0.0512(7) 0.0626(8) 0.0051(6) 0.0157(7) 0.0176(7) C13 0.0757(9) 0.0647(8) 0.0634(9) -0.0029(7) 0.0085(8) -0.0041(8) C14 0.071(1) 0.073(1) 0.089(1) 0.0141(9) 0.0087(9) 0.0142(8) C15 0.081(1) 0.083(1) 0.075(1) 0.0200(9) 0.0185(9) 0.0194(9) C16 0.071(1) 0.0701(9) 0.070(1) -0.0004(8) -0.0006(8) -0.0212(8) C17 0.098(2) 0.125(2) 0.082(1) -0.005(1) -0.011(1) 0.050(2) C18 0.117(2) 0.0516(8) 0.090(1) -0.0117(8) 0.009(1) -0.0120(9) C19 0.125(2) 0.0674(9) 0.0576(9) -0.0118(8) -0.007(1) -0.005(1) C20 0.0689(9) 0.081(1) 0.0513(8) -0.0107(7) 0.0158(7) -0.0039(8) C21 0.115(2) 0.077(1) 0.115(2) -0.023(1) -0.006(1) -0.024(1) C22 0.102(2) 0.132(2) 0.066(1) 0.024(1) 0.016(1) 0.053(2) C23 0.127(2) 0.071(1) 0.0533(8) -0.0076(8) 0.021(1) 0.008(1) C24 0.0506(7) 0.0767(9) 0.0604(8) -0.0068(7) -0.0038(6) -0.0021(7) C25 0.065(1) 0.122(2) 0.110(2) -0.027(1) -0.016(1) -0.014(1) C26 0.070(1) 0.095(1) 0.134(2) 0.005(1) -0.012(1) 0.020(1) C27 0.178(3) 0.154(2) 0.082(1) -0.022(2) 0.047(2) -0.103(2) C28 0.0574(8) 0.094(1) 0.080(1) -0.0101(9) 0.0121(8) 0.0069(8) C29 0.070(1) 0.123(2) 0.191(3) 0.023(2) -0.026(2) -0.031(1) _refine_ls_extinction_coef 612.9(404) _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 O1 . C6 . 1.332(2) yes O1 . C16 . 1.476(2) yes O2 . C6 . 1.202(2) yes N3 . C5 . 1.458(2) yes N3 . C9 . 1.461(2) yes N3 . C10 . 1.479(2) yes C4 . C6 . 1.510(2) yes C4 . C9 . 1.561(2) yes C4 . C20 . 1.540(2) yes C4 . H41 . 1.000 no C5 . C7 . 1.521(2) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C7 . C8 . 1.373(2) yes C7 . C13 . 1.394(2) yes C8 . C19 . 1.387(2) yes C8 . H81 . 1.000 no C9 . C24 . 1.533(2) yes C9 . H91 . 1.000 no C10 . C12 . 1.527(2) yes C10 . C18 . 1.517(3) yes C10 . H101 . 1.000 no C11 . C13 . 1.395(2) yes C11 . C23 . 1.369(3) yes C11 . H111 . 1.000 no C12 . C14 . 1.385(3) yes C12 . C15 . 1.388(2) yes C13 . H131 . 1.000 no C14 . C26 . 1.389(4) yes C14 . H141 . 1.000 no C15 . C22 . 1.382(3) yes C15 . H151 . 1.000 no C16 . C21 . 1.491(3) yes C16 . C27 . 1.501(3) yes C16 . C29 . 1.515(3) yes C17 . C22 . 1.356(4) yes C17 . C26 . 1.373(4) yes C17 . H171 . 1.000 no C18 . H181 . 1.000 no C18 . H182 . 1.000 no C18 . H183 . 1.000 no C19 . C23 . 1.358(3) yes C19 . H191 . 1.000 no C20 . C28 . 1.518(3) yes C20 . H201 . 1.000 no C20 . H202 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no C22 . H221 . 1.000 no C23 . H231 . 1.000 no C24 . C25 . 1.516(3) yes C24 . C28 . 1.539(2) yes C24 . H241 . 1.000 no C25 . H251 . 1.000 no C25 . H252 . 1.000 no C25 . H253 . 1.000 no C26 . H261 . 1.000 no C27 . H271 . 1.000 no C27 . H272 . 1.000 no C27 . H273 . 1.000 no C28 . H281 . 1.000 no C28 . H282 . 1.000 no C29 . H291 . 1.000 no C29 . H292 . 1.000 no C29 . H293 . 1.000 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 C6 . O1 . C16 . 121.7(1) no C5 . N3 . C9 . 115.8(1) no C5 . N3 . C10 . 114.8(1) no C9 . N3 . C10 . 116.1(1) no C6 . C4 . C9 . 116.5(1) no C6 . C4 . C20 . 108.1(1) no C9 . C4 . C20 . 101.1(1) no C6 . C4 . H41 . 101.99 no C9 . C4 . H41 . 111.41 no C20 . C4 . H41 . 118.43 no N3 . C5 . C7 . 114.1(1) no N3 . C5 . H51 . 108.31 no C7 . C5 . H51 . 108.29 no N3 . C5 . H52 . 108.32 no C7 . C5 . H52 . 108.33 no H51 . C5 . H52 . 109.45 no O1 . C6 . O2 . 124.4(1) no O1 . C6 . C4 . 110.4(1) no O2 . C6 . C4 . 125.1(1) no C5 . C7 . C8 . 123.0(1) no C5 . C7 . C13 . 118.7(1) no C8 . C7 . C13 . 118.2(1) no C7 . C8 . C19 . 121.0(2) no C7 . C8 . H81 . 119.48 no C19 . C8 . H81 . 119.52 no N3 . C9 . C4 . 121.5(1) no N3 . C9 . C24 . 114.6(1) no C4 . C9 . C24 . 104.3(1) no N3 . C9 . H91 . 90.36 no C4 . C9 . H91 . 110.03 no C24 . C9 . H91 . 116.16 no N3 . C10 . C12 . 113.4(1) no N3 . C10 . C18 . 110.3(2) no C12 . C10 . C18 . 113.6(1) no N3 . C10 . H101 . 105.86 no C12 . C10 . H101 . 105.20 no C18 . C10 . H101 . 107.94 no C13 . C11 . C23 . 119.7(2) no C13 . C11 . H111 . 120.18 no C23 . C11 . H111 . 120.11 no C10 . C12 . C14 . 120.0(1) no C10 . C12 . C15 . 122.5(2) no C14 . C12 . C15 . 117.4(2) no C7 . C13 . C11 . 120.4(2) no C7 . C13 . H131 . 119.83 no C11 . C13 . H131 . 119.74 no C12 . C14 . C26 . 121.1(2) no C12 . C14 . H141 . 119.30 no C26 . C14 . H141 . 119.54 no C12 . C15 . C22 . 121.1(2) no C12 . C15 . H151 . 119.46 no C22 . C15 . H151 . 119.51 no O1 . C16 . C21 . 110.9(2) no O1 . C16 . C27 . 109.2(1) no C21 . C16 . C27 . 112.6(2) no O1 . C16 . C29 . 102.5(2) no C21 . C16 . C29 . 108.4(2) no C27 . C16 . C29 . 112.9(3) no C22 . C17 . C26 . 119.6(2) no C22 . C17 . H171 . 120.11 no C26 . C17 . H171 . 120.22 no C10 . C18 . H181 . 109.53 no C10 . C18 . H182 . 109.49 no H181 . C18 . H182 . 109.57 no C10 . C18 . H183 . 109.43 no H181 . C18 . H183 . 109.44 no H182 . C18 . H183 . 109.38 no C8 . C19 . C23 . 120.3(2) no C8 . C19 . H191 . 119.91 no C23 . C19 . H191 . 119.83 no C4 . C20 . C28 . 107.0(1) no C4 . C20 . H201 . 110.11 no C28 . C20 . H201 . 110.06 no C4 . C20 . H202 . 110.06 no C28 . C20 . H202 . 110.12 no H201 . C20 . H202 . 109.47 no C16 . C21 . H211 . 109.55 no C16 . C21 . H212 . 109.63 no H211 . C21 . H212 . 109.47 no C16 . C21 . H213 . 109.49 no H211 . C21 . H213 . 109.28 no H212 . C21 . H213 . 109.42 no C15 . C22 . C17 . 120.7(2) no C15 . C22 . H221 . 119.63 no C17 . C22 . H221 . 119.63 no C11 . C23 . C19 . 120.4(2) no C11 . C23 . H231 . 119.90 no C19 . C23 . H231 . 119.73 no C9 . C24 . C25 . 113.1(2) no C9 . C24 . C28 . 103.3(1) no C25 . C24 . C28 . 114.4(2) no C9 . C24 . H241 . 113.30 no C25 . C24 . H241 . 100.93 no C28 . C24 . H241 . 112.38 no C24 . C25 . H251 . 109.49 no C24 . C25 . H252 . 109.49 no H251 . C25 . H252 . 109.49 no C24 . C25 . H253 . 109.45 no H251 . C25 . H253 . 109.38 no H252 . C25 . H253 . 109.53 no C14 . C26 . C17 . 120.0(2) no C14 . C26 . H261 . 120.05 no C17 . C26 . H261 . 119.96 no C16 . C27 . H271 . 109.54 no C16 . C27 . H272 . 109.51 no H271 . C27 . H272 . 109.35 no C16 . C27 . H273 . 109.59 no H271 . C27 . H273 . 109.48 no H272 . C27 . H273 . 109.34 no C20 . C28 . C24 . 107.7(1) no C20 . C28 . H281 . 109.89 no C24 . C28 . H281 . 110.02 no C20 . C28 . H282 . 109.83 no C24 . C28 . H282 . 109.94 no H281 . C28 . H282 . 109.45 no C16 . C29 . H291 . 109.48 no C16 . C29 . H292 . 109.40 no H291 . C29 . H292 . 109.49 no C16 . C29 . H293 . 109.44 no H291 . C29 . H293 . 109.56 no H292 . C29 . H293 . 109.46 no