data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Stephen G. 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 ' 01865 275646 ' _publ_contact_author_fax ' 01865 275633 ' loop_ _publ_author_name _publ_author_address S.G.Davies ;Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UK ; A.C.Garner ;Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UK ; E.C.Goddard ;Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UK ; D.Kruchinin ;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.D.Smith ; ;Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UK ; H.Rodriguez-Solla ;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 ; S.M.Toms ;Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UK ; # 1051654 pr60 # 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 Paul M. Roberts ' #============================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition ; #============================================================================== # 4. TEXT _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 # see also _refine_ls_hydrogen for refinement keywords. ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; #========================================================================== data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 629877' _audit_creation_date 05-05-01 _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 9.5595(2) _cell_angle_alpha 90 _cell_length_b 17.1047(5) _cell_angle_beta 98.2945(16) _cell_length_c 13.6097(3) _cell_angle_gamma 90 _cell_volume 2202.08(9) _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 4 _chemical_formula_sum ' C26 H28 N2 O1 ' _chemical_formula_moiety ' C26 H28 N2 O1 ' _chemical_compound_source ; ? ; _chemical_formula_weight 384.52 _cell_measurement_reflns_used 4221 _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 1.160 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 824.000 _exptl_absorpt_coefficient_mu 0.071 # 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 8467 _reflns_number_total 5060 _diffrn_reflns_av_R_equivalents 0.02 # Number of reflections with Friedels Law is 5060 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5047 _diffrn_reflns_theta_min 5.129 _diffrn_reflns_theta_max 27.485 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 24.393 _diffrn_measured_fraction_theta_full 0.985 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 22 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _refine_diff_density_min -0.16 _refine_diff_density_max 0.18 _refine_ls_number_reflns 4299 _refine_ls_number_parameters 523 #_refine_ls_R_factor_ref 0.0469 _refine_ls_wR_factor_ref 0.0580 _refine_ls_goodness_of_fit_ref 1.0904 #_reflns_number_all 5060 _refine_ls_R_factor_all 0.0583 _refine_ls_wR_factor_all 0.0748 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.50u(I) _reflns_number_gt 4299 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_gt 0.0580 _refine_ls_shift/su_max 0.000191 _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 1.43 0.829 1.03 ; _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 C1 C 0.7451(3) 0.24468(16) -0.19753(18) 0.0454 1.0000 Uani . N2 N 0.8241(2) 0.17987(14) -0.14660(15) 0.0468 1.0000 Uani . C3 C 0.7469(3) 0.10495(18) -0.14822(19) 0.0524 1.0000 Uani . C4 C 0.7187(3) 0.07500(15) -0.25520(18) 0.0461 1.0000 Uani . C5 C 0.8322(3) 0.05983(17) -0.3049(2) 0.0555 1.0000 Uani . C6 C 0.8136(4) 0.03835(18) -0.4037(2) 0.0632 1.0000 Uani . C7 C 0.6777(4) 0.03198(19) -0.4554(2) 0.0667 1.0000 Uani . C8 C 0.5639(3) 0.04392(18) -0.4069(2) 0.0650 1.0000 Uani . C9 C 0.5825(3) 0.06539(16) -0.3068(2) 0.0537 1.0000 Uani . C10 C 0.6144(4) 0.1066(3) -0.0969(2) 0.0808 1.0000 Uani . C11 C 0.9067(3) 0.19924(19) -0.04990(19) 0.0540 1.0000 Uani . C12 C 1.0295(2) 0.14372(17) -0.02378(18) 0.0486 1.0000 Uani . C13 C 1.1263(3) 0.1334(2) -0.0898(2) 0.0576 1.0000 Uani . C14 C 1.2407(3) 0.0833(2) -0.0655(2) 0.0665 1.0000 Uani . C15 C 1.2596(3) 0.0443(2) 0.0237(3) 0.0684 1.0000 Uani . C16 C 1.1653(3) 0.0547(2) 0.0899(2) 0.0644 1.0000 Uani . C17 C 1.0503(3) 0.10465(18) 0.06628(19) 0.0536 1.0000 Uani . C18 C 0.8370(2) 0.30191(16) -0.24674(19) 0.0460 1.0000 Uani . C19 C 0.7409(3) 0.37311(16) -0.2646(2) 0.0499 1.0000 Uani . N20 N 0.6457(2) 0.36948(14) -0.20111(18) 0.0534 1.0000 Uani . C21 C 0.6586(3) 0.29999(19) -0.1388(2) 0.0562 1.0000 Uani . O22 O 0.7481(2) 0.42464(12) -0.32684(18) 0.0630 1.0000 Uani . C23 C 0.8908(3) 0.27137(16) -0.34087(18) 0.0481 1.0000 Uani . C24 C 1.0489(2) 0.27236(15) -0.33613(16) 0.0417 1.0000 Uani . C25 C 1.1225(3) 0.2039(2) -0.3505(2) 0.0625 1.0000 Uani . C26 C 1.2668(4) 0.2052(3) -0.3488(3) 0.0923 1.0000 Uani . C27 C 1.3402(4) 0.2732(5) -0.3325(3) 0.1131 1.0000 Uani . C28 C 1.2695(5) 0.3421(4) -0.3180(4) 0.1077 1.0000 Uani . C29 C 1.1248(4) 0.3415(2) -0.3198(3) 0.0697 1.0000 Uani . C30 C 0.4867(2) 0.19371(15) 0.29074(17) 0.0420 1.0000 Uani . N31 N 0.4148(2) 0.26441(13) 0.24900(16) 0.0464 1.0000 Uani . C32 C 0.4266(3) 0.33255(16) 0.3164(2) 0.0522 1.0000 Uani . C33 C 0.5764(3) 0.36585(15) 0.3231(2) 0.0526 1.0000 Uani . C34 C 0.6265(4) 0.38514(19) 0.2349(2) 0.0648 1.0000 Uani . C35 C 0.7604(5) 0.4168(2) 0.2364(4) 0.0905 1.0000 Uani . C36 C 0.8464(5) 0.4297(2) 0.3252(5) 0.1003 1.0000 Uani . C37 C 0.7977(5) 0.4115(2) 0.4132(4) 0.0926 1.0000 Uani . C38 C 0.6629(4) 0.37972(19) 0.4120(3) 0.0685 1.0000 Uani . C39 C 0.3792(4) 0.3167(2) 0.4173(3) 0.0683 1.0000 Uani . C40 C 0.2699(3) 0.25195(17) 0.1989(2) 0.0545 1.0000 Uani . C41 C 0.2278(3) 0.31153(18) 0.1184(2) 0.0546 1.0000 Uani . C42 C 0.1089(3) 0.3580(2) 0.1190(2) 0.0624 1.0000 Uani . C43 C 0.0685(4) 0.4114(2) 0.0428(3) 0.0742 1.0000 Uani . C44 C 0.1449(5) 0.4188(3) -0.0337(3) 0.0842 1.0000 Uani . C45 C 0.2634(5) 0.3731(3) -0.0355(3) 0.0990 1.0000 Uani . C46 C 0.3053(4) 0.3200(3) 0.0398(3) 0.0796 1.0000 Uani . C47 C 0.5344(3) 0.14176(16) 0.20960(17) 0.0447 1.0000 Uani . C48 C 0.5084(2) 0.05855(15) 0.24018(17) 0.0442 1.0000 Uani . N49 N 0.4341(2) 0.05951(13) 0.31670(15) 0.0470 1.0000 Uani . C50 C 0.3997(3) 0.13721(16) 0.34973(19) 0.0497 1.0000 Uani . O51 O 0.54443(19) -0.00102(11) 0.19851(15) 0.0530 1.0000 Uani . C52 C 0.6837(3) 0.15633(17) 0.18453(18) 0.0503 1.0000 Uani . C53 C 0.8051(2) 0.14492(17) 0.26773(17) 0.0468 1.0000 Uani . C54 C 0.8654(3) 0.07132(18) 0.2861(2) 0.0542 1.0000 Uani . C55 C 0.9830(3) 0.0618(2) 0.3582(2) 0.0626 1.0000 Uani . C56 C 1.0394(3) 0.1247(2) 0.4133(2) 0.0630 1.0000 Uani . C57 C 0.9796(3) 0.1973(2) 0.3978(2) 0.0637 1.0000 Uani . C58 C 0.8634(3) 0.20799(19) 0.3241(2) 0.0562 1.0000 Uani . H11 H 0.6784 0.2117 -0.2459 0.0594 1.0000 Uiso . H31 H 0.8100 0.0652 -0.1090 0.0664 1.0000 Uiso . H51 H 0.9307 0.0646 -0.2671 0.0679 1.0000 Uiso . H61 H 0.8988 0.0273 -0.4385 0.0776 1.0000 Uiso . H71 H 0.6647 0.0201 -0.5290 0.0838 1.0000 Uiso . H81 H 0.4652 0.0364 -0.4438 0.0793 1.0000 Uiso . H91 H 0.4993 0.0741 -0.2713 0.0656 1.0000 Uiso . H101 H 0.5648 0.0548 -0.1007 0.1110 1.0000 Uiso . H102 H 0.6386 0.1220 -0.0251 0.1110 1.0000 Uiso . H103 H 0.5442 0.1471 -0.1300 0.1110 1.0000 Uiso . H111 H 0.9438 0.2542 -0.0517 0.0695 1.0000 Uiso . H112 H 0.8433 0.1964 0.0032 0.0695 1.0000 Uiso . H131 H 1.1118 0.1620 -0.1554 0.0719 1.0000 Uiso . H141 H 1.3113 0.0761 -0.1160 0.0829 1.0000 Uiso . H151 H 1.3453 0.0078 0.0397 0.0783 1.0000 Uiso . H161 H 1.1792 0.0263 0.1556 0.0772 1.0000 Uiso . H171 H 0.9804 0.1127 0.1149 0.0654 1.0000 Uiso . H181 H 0.9291 0.3131 -0.2027 0.0575 1.0000 Uiso . H211 H 0.7106 0.3112 -0.0685 0.0717 1.0000 Uiso . H212 H 0.5627 0.2775 -0.1287 0.0717 1.0000 Uiso . H231 H 0.8489 0.3055 -0.3985 0.0623 1.0000 Uiso . H232 H 0.8553 0.2167 -0.3539 0.0623 1.0000 Uiso . H251 H 1.0686 0.1536 -0.3626 0.0780 1.0000 Uiso . H261 H 1.3196 0.1550 -0.3587 0.1097 1.0000 Uiso . H271 H 1.4453 0.2748 -0.3330 0.1248 1.0000 Uiso . H281 H 1.3238 0.3928 -0.3058 0.1345 1.0000 Uiso . H291 H 1.0738 0.3914 -0.3105 0.0910 1.0000 Uiso . H301 H 0.5678 0.2152 0.3390 0.0548 1.0000 Uiso . H321 H 0.3573 0.3737 0.2862 0.0668 1.0000 Uiso . H341 H 0.5646 0.3752 0.1697 0.0821 1.0000 Uiso . H351 H 0.7957 0.4267 0.1699 0.1179 1.0000 Uiso . H361 H 0.9435 0.4545 0.3256 0.1226 1.0000 Uiso . H371 H 0.8579 0.4222 0.4797 0.1095 1.0000 Uiso . H381 H 0.6269 0.3661 0.4774 0.0818 1.0000 Uiso . H391 H 0.3905 0.3654 0.4597 0.0916 1.0000 Uiso . H392 H 0.4403 0.2744 0.4532 0.0916 1.0000 Uiso . H393 H 0.2786 0.2997 0.4093 0.0916 1.0000 Uiso . H401 H 0.2012 0.2549 0.2493 0.0685 1.0000 Uiso . H402 H 0.2616 0.1977 0.1690 0.0685 1.0000 Uiso . H421 H 0.0518 0.3523 0.1776 0.0801 1.0000 Uiso . H431 H -0.0209 0.4435 0.0433 0.0896 1.0000 Uiso . H441 H 0.1133 0.4586 -0.0886 0.1023 1.0000 Uiso . H451 H 0.3242 0.3803 -0.0900 0.1253 1.0000 Uiso . H461 H 0.3922 0.2859 0.0395 0.0958 1.0000 Uiso . H471 H 0.4769 0.1563 0.1439 0.0553 1.0000 Uiso . H501 H 0.4276 0.1433 0.4239 0.0637 1.0000 Uiso . H502 H 0.2952 0.1486 0.3338 0.0637 1.0000 Uiso . H521 H 0.6881 0.2107 0.1579 0.0627 1.0000 Uiso . H522 H 0.6986 0.1185 0.1288 0.0627 1.0000 Uiso . H541 H 0.8231 0.0244 0.2463 0.0708 1.0000 Uiso . H551 H 1.0282 0.0080 0.3696 0.0793 1.0000 Uiso . H561 H 1.1240 0.1167 0.4666 0.0773 1.0000 Uiso . H571 H 1.0192 0.2439 0.4381 0.0788 1.0000 Uiso . H581 H 0.8208 0.2616 0.3109 0.0681 1.0000 Uiso . H491 H 0.3794 0.0055 0.3255 0.0500 1.0000 Uiso . H201 H 0.5719 0.4046 -0.2052 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 0.0376(11) 0.0531(14) 0.0441(12) -0.000(1) 0.0008(9) 0.003(1) N2 0.039(1) 0.0577(13) 0.042(1) 0.0006(9) -0.0016(8) 0.0020(9) C3 0.0435(12) 0.0662(16) 0.0451(12) 0.0141(12) -0.002(1) -0.0056(12) C4 0.0461(12) 0.0417(12) 0.0478(12) 0.012(1) -0.002(1) -0.002(1) C5 0.0506(14) 0.0532(15) 0.0606(14) 0.0083(13) 0.0009(11) 0.0004(12) C6 0.0752(19) 0.0518(16) 0.0629(16) -0.0023(13) 0.0108(14) 0.0025(14) C7 0.089(2) 0.0497(15) 0.0574(16) -0.0018(13) -0.0039(15) 0.0007(15) C8 0.0676(18) 0.0536(16) 0.0647(16) 0.0037(14) -0.0219(14) -0.0047(14) C9 0.0496(13) 0.0460(14) 0.0620(15) 0.0091(12) -0.0045(11) -0.0007(11) C10 0.0625(18) 0.129(3) 0.0530(16) 0.0076(19) 0.0145(13) -0.022(2) C11 0.0467(13) 0.0737(18) 0.0396(12) -0.0029(12) -0.0005(9) 0.0075(13) C12 0.0368(11) 0.0627(15) 0.0436(12) -0.0031(12) -0.0028(9) -0.0016(11) C13 0.0432(12) 0.078(2) 0.0501(13) 0.0061(14) 0.003(1) -0.0005(13) C14 0.0409(13) 0.085(2) 0.0720(18) -0.0105(16) 0.0014(12) 0.0001(14) C15 0.0513(15) 0.0671(19) 0.0772(19) -0.0102(16) -0.0231(14) 0.0053(14) C16 0.0686(18) 0.0610(17) 0.0551(14) 0.0051(14) -0.0202(14) -0.0097(14) C17 0.0514(13) 0.0663(16) 0.0400(12) -0.0008(12) -0.004(1) -0.0163(13) C18 0.0366(11) 0.0513(14) 0.0496(12) -0.0097(11) 0.0043(9) -0.002(1) C19 0.0432(12) 0.0470(14) 0.0596(14) -0.0124(12) 0.0083(11) -0.004(1) N20 0.043(1) 0.0537(12) 0.0645(13) -0.0045(11) 0.010(1) 0.0049(9) C21 0.0471(13) 0.0714(18) 0.0513(13) -0.0006(13) 0.0112(11) 0.0107(13) O22 0.0673(12) 0.043(1) 0.0839(13) -0.003(1) 0.0279(11) -0.0017(9) C23 0.0436(12) 0.0539(15) 0.0464(12) -0.0090(11) 0.0052(9) -0.0015(11) C24 0.0400(11) 0.0486(13) 0.036(1) 0.0007(9) 0.0042(8) 0.003(1) C25 0.0689(18) 0.0690(19) 0.0515(14) 0.0070(14) 0.0147(13) 0.0246(15) C26 0.064(2) 0.156(4) 0.0566(18) -0.000(2) 0.0061(15) 0.052(3) C27 0.0428(15) 0.241(7) 0.0549(18) -0.037(3) 0.0052(13) -0.004(3) C28 0.076(2) 0.160(5) 0.093(3) -0.046(3) 0.032(2) -0.061(3) C29 0.0677(19) 0.073(2) 0.0724(19) -0.0158(16) 0.0224(15) -0.0243(16) C30 0.0423(11) 0.0432(12) 0.039(1) 0.0070(9) 0.0014(9) -0.002(1) N31 0.045(1) 0.041(1) 0.0508(11) 0.0054(9) 0.0004(8) -0.0007(8) C32 0.0576(15) 0.0424(13) 0.0575(14) 0.0042(11) 0.0114(12) -0.0011(11) C33 0.0570(14) 0.0414(13) 0.0581(14) 0.0074(12) 0.0034(12) -0.0078(11) C34 0.0695(18) 0.0545(16) 0.0702(17) 0.0207(14) 0.0088(14) -0.0089(14) C35 0.081(2) 0.072(2) 0.123(3) 0.029(2) 0.030(2) -0.018(2) C36 0.082(3) 0.065(2) 0.150(5) 0.011(3) 0.005(3) -0.034(2) C37 0.086(3) 0.069(2) 0.113(3) -0.011(2) -0.021(2) -0.022(2) C38 0.081(2) 0.0514(16) 0.0679(18) -0.0009(14) -0.0056(15) -0.0078(15) C39 0.085(2) 0.0575(17) 0.0677(18) -0.0063(15) 0.0306(16) -0.0065(16) C40 0.0442(13) 0.0488(14) 0.0671(16) 0.0086(12) -0.0037(11) -0.0006(11) C41 0.0503(14) 0.0556(15) 0.0542(14) -0.0010(12) -0.0046(11) 0.0041(12) C42 0.0626(16) 0.0590(17) 0.0635(16) 0.0062(14) 0.0025(13) 0.0118(14) C43 0.077(2) 0.068(2) 0.074(2) 0.0076(16) -0.0031(16) 0.0229(16) C44 0.099(3) 0.091(3) 0.0576(17) 0.0159(18) -0.0037(17) 0.027(2) C45 0.110(3) 0.132(4) 0.0575(18) 0.026(2) 0.0195(19) 0.039(3) C46 0.079(2) 0.101(3) 0.0591(17) 0.0111(19) 0.0111(15) 0.034(2) C47 0.0469(12) 0.0493(13) 0.036(1) 0.005(1) 0.0006(9) 0.0006(11) C48 0.034(1) 0.0499(13) 0.0453(11) 0.0030(11) -0.0065(9) -0.004(1) N49 0.047(1) 0.0457(11) 0.048(1) 0.0049(9) 0.0042(8) -0.0042(9) C50 0.0517(13) 0.0471(13) 0.0517(13) 0.0080(11) 0.012(1) -0.0010(11) O51 0.0461(9) 0.050(1) 0.0621(11) -0.0039(9) 0.0036(8) 0.0010(8) C52 0.0510(13) 0.0628(16) 0.0383(11) 0.0028(11) 0.010(1) -0.0046(12) C53 0.0397(11) 0.0638(15) 0.0389(11) 0.0005(11) 0.0123(9) -0.0063(11) C54 0.0488(13) 0.0643(17) 0.0508(13) -0.0060(13) 0.0110(11) 0.0035(12) C55 0.0486(14) 0.083(2) 0.0563(15) 0.0013(15) 0.0063(11) 0.0117(14) C56 0.0401(12) 0.095(2) 0.0530(14) -0.0019(15) 0.0047(11) -0.0038(14) C57 0.0493(14) 0.081(2) 0.0604(16) -0.0086(16) 0.0047(12) -0.0159(15) C58 0.0488(13) 0.0633(17) 0.0565(14) -0.0016(13) 0.0081(11) -0.0121(12) _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 C1 . N2 . 1.459(3) yes C1 . C18 . 1.532(4) yes C1 . C21 . 1.552(4) yes C1 . H11 . 1.019 no N2 . C3 . 1.477(4) yes N2 . C11 . 1.471(3) yes C3 . C4 . 1.530(4) yes C3 . C10 . 1.532(4) yes C3 . H31 . 1.009 no C4 . C5 . 1.384(4) yes C4 . C9 . 1.397(3) yes C5 . C6 . 1.380(4) yes C5 . H51 . 1.008 no C6 . C7 . 1.390(5) yes C6 . H61 . 1.017 no C7 . C8 . 1.368(5) yes C7 . H71 . 1.011 no C8 . C9 . 1.397(4) yes C8 . H81 . 1.011 no C9 . H91 . 0.999 no C10 . H101 . 1.003 no C10 . H102 . 1.007 no C10 . H103 . 1.022 no C11 . C12 . 1.512(4) yes C11 . H111 . 1.006 no C11 . H112 . 1.009 no C12 . C13 . 1.391(4) yes C12 . C17 . 1.385(4) yes C13 . C14 . 1.391(4) yes C13 . H131 . 1.010 no C14 . C15 . 1.373(5) yes C14 . H141 . 1.038 no C15 . C16 . 1.375(5) yes C15 . H151 . 1.029 no C16 . C17 . 1.392(5) yes C16 . H161 . 1.010 no C17 . H171 . 1.015 no C18 . C19 . 1.524(4) yes C18 . C23 . 1.539(3) yes C18 . H181 . 1.010 no C19 . N20 . 1.343(3) yes C19 . O22 . 1.232(4) yes N20 . C21 . 1.455(4) yes N20 . H201 . 0.922 no C21 . H211 . 1.031 no C21 . H212 . 1.021 no C23 . C24 . 1.504(3) yes C23 . H231 . 1.013 no C23 . H232 . 1.002 no C24 . C25 . 1.394(4) yes C24 . C29 . 1.388(4) yes C25 . C26 . 1.377(5) yes C25 . H251 . 1.004 no C26 . C27 . 1.359(8) yes C26 . H261 . 1.015 no C27 . C28 . 1.388(9) yes C27 . H271 . 1.006 no C28 . C29 . 1.380(6) yes C28 . H281 . 1.011 no C29 . H291 . 1.000 no C30 . N31 . 1.464(3) yes C30 . C47 . 1.537(4) yes C30 . C50 . 1.569(3) yes C30 . H301 . 1.011 no N31 . C32 . 1.477(4) yes N31 . C40 . 1.469(3) yes C32 . C33 . 1.531(4) yes C32 . C39 . 1.531(4) yes C32 . H321 . 1.013 no C33 . C34 . 1.395(4) yes C33 . C38 . 1.384(4) yes C34 . C35 . 1.387(5) yes C34 . H341 . 1.007 no C35 . C36 . 1.378(7) yes C35 . H351 . 1.025 no C36 . C37 . 1.381(7) yes C36 . H361 . 1.021 no C37 . C38 . 1.397(6) yes C37 . H371 . 1.016 no C38 . H381 . 1.025 no C39 . H391 . 1.011 no C39 . H392 . 1.010 no C39 . H393 . 0.996 no C40 . C41 . 1.507(4) yes C40 . H401 . 1.017 no C40 . H402 . 1.012 no C41 . C42 . 1.388(4) yes C41 . C46 . 1.394(5) yes C42 . C43 . 1.395(5) yes C42 . H421 . 1.034 no C43 . C44 . 1.361(6) yes C43 . H431 . 1.017 no C44 . C45 . 1.380(6) yes C44 . H441 . 1.024 no C45 . C46 . 1.385(6) yes C45 . H451 . 1.014 no C46 . H461 . 1.015 no C47 . C48 . 1.514(4) yes C47 . C52 . 1.535(4) yes C47 . H471 . 1.011 no C48 . N49 . 1.343(3) yes C48 . O51 . 1.239(3) yes N49 . C50 . 1.456(4) yes N49 . H491 . 1.076 no C50 . H501 . 1.012 no C50 . H502 . 1.010 no C52 . C53 . 1.513(4) yes C52 . H521 . 1.001 no C52 . H522 . 1.023 no C53 . C54 . 1.392(4) yes C53 . C58 . 1.393(4) yes C54 . C55 . 1.391(4) yes C54 . H541 . 1.019 no C55 . C56 . 1.377(5) yes C55 . H551 . 1.019 no C56 . C57 . 1.371(5) yes C56 . H561 . 1.015 no C57 . C58 . 1.396(4) yes C57 . H571 . 1.009 no C58 . H581 . 1.010 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 N2 . C1 . C18 . 113.7(2) yes N2 . C1 . C21 . 119.8(2) yes C18 . C1 . C21 . 102.6(2) yes N2 . C1 . H11 . 96.835 no C18 . C1 . H11 . 114.619 no C21 . C1 . H11 . 109.876 no C1 . N2 . C3 . 115.37(19) yes C1 . N2 . C11 . 115.3(2) yes C3 . N2 . C11 . 114.3(2) yes N2 . C3 . C4 . 108.9(2) yes N2 . C3 . C10 . 114.9(3) yes C4 . C3 . C10 . 113.3(2) yes N2 . C3 . H31 . 108.507 no C4 . C3 . H31 . 106.718 no C10 . C3 . H31 . 103.975 no C3 . C4 . C5 . 119.0(2) yes C3 . C4 . C9 . 122.8(2) yes C5 . C4 . C9 . 118.2(2) yes C4 . C5 . C6 . 121.7(3) yes C4 . C5 . H51 . 118.383 no C6 . C5 . H51 . 119.874 no C5 . C6 . C7 . 119.6(3) yes C5 . C6 . H61 . 120.227 no C7 . C6 . H61 . 120.165 no C6 . C7 . C8 . 119.6(3) yes C6 . C7 . H71 . 119.348 no C8 . C7 . H71 . 120.994 no C7 . C8 . C9 . 120.8(3) yes C7 . C8 . H81 . 119.413 no C9 . C8 . H81 . 119.804 no C4 . C9 . C8 . 120.0(3) yes C4 . C9 . H91 . 119.277 no C8 . C9 . H91 . 120.747 no C3 . C10 . H101 . 112.151 no C3 . C10 . H102 . 111.024 no H101 . C10 . H102 . 108.662 no C3 . C10 . H103 . 110.198 no H101 . C10 . H103 . 107.460 no H102 . C10 . H103 . 107.155 no N2 . C11 . C12 . 111.5(2) yes N2 . C11 . H111 . 109.524 no C12 . C11 . H111 . 109.092 no N2 . C11 . H112 . 109.252 no C12 . C11 . H112 . 109.136 no H111 . C11 . H112 . 108.255 no C11 . C12 . C13 . 119.6(2) yes C11 . C12 . C17 . 121.2(2) yes C13 . C12 . C17 . 119.1(3) yes C12 . C13 . C14 . 119.8(3) yes C12 . C13 . H131 . 119.371 no C14 . C13 . H131 . 120.790 no C13 . C14 . C15 . 120.5(3) yes C13 . C14 . H141 . 118.666 no C15 . C14 . H141 . 120.806 no C14 . C15 . C16 . 120.1(3) yes C14 . C15 . H151 . 118.786 no C16 . C15 . H151 . 121.129 no C15 . C16 . C17 . 119.9(3) yes C15 . C16 . H161 . 120.183 no C17 . C16 . H161 . 119.919 no C12 . C17 . C16 . 120.5(3) yes C12 . C17 . H171 . 119.202 no C16 . C17 . H171 . 120.281 no C1 . C18 . C19 . 102.1(2) yes C1 . C18 . C23 . 115.4(2) yes C19 . C18 . C23 . 113.9(2) yes C1 . C18 . H181 . 111.552 no C19 . C18 . H181 . 113.421 no C23 . C18 . H181 . 100.978 no C18 . C19 . N20 . 108.0(2) yes C18 . C19 . O22 . 126.1(2) yes N20 . C19 . O22 . 125.9(3) yes C19 . N20 . C21 . 113.8(2) yes C19 . N20 . H201 . 120.922 no C21 . N20 . H201 . 124.594 no C1 . C21 . N20 . 101.8(2) yes C1 . C21 . H211 . 111.698 no N20 . C21 . H211 . 112.229 no C1 . C21 . H212 . 113.280 no N20 . C21 . H212 . 112.585 no H211 . C21 . H212 . 105.465 no C18 . C23 . C24 . 114.54(19) yes C18 . C23 . H231 . 107.871 no C24 . C23 . H231 . 108.032 no C18 . C23 . H232 . 108.570 no C24 . C23 . H232 . 109.349 no H231 . C23 . H232 . 108.305 no C23 . C24 . C25 . 120.6(3) yes C23 . C24 . C29 . 121.0(2) yes C25 . C24 . C29 . 118.4(3) yes C24 . C25 . C26 . 120.5(4) yes C24 . C25 . H251 . 119.070 no C26 . C25 . H251 . 120.404 no C25 . C26 . C27 . 120.6(4) yes C25 . C26 . H261 . 119.991 no C27 . C26 . H261 . 119.398 no C26 . C27 . C28 . 120.0(3) yes C26 . C27 . H271 . 120.942 no C28 . C27 . H271 . 119.039 no C27 . C28 . C29 . 119.9(4) yes C27 . C28 . H281 . 120.161 no C29 . C28 . H281 . 119.979 no C24 . C29 . C28 . 120.6(4) yes C24 . C29 . H291 . 119.631 no C28 . C29 . H291 . 119.740 no N31 . C30 . C47 . 111.72(19) yes N31 . C30 . C50 . 117.0(2) yes C47 . C30 . C50 . 104.2(2) yes N31 . C30 . H301 . 102.988 no C47 . C30 . H301 . 113.461 no C50 . C30 . H301 . 107.748 no C30 . N31 . C32 . 114.89(19) yes C30 . N31 . C40 . 114.8(2) yes C32 . N31 . C40 . 112.7(2) yes N31 . C32 . C33 . 108.5(2) yes N31 . C32 . C39 . 114.2(2) yes C33 . C32 . C39 . 114.1(3) yes N31 . C32 . H321 . 107.984 no C33 . C32 . H321 . 108.517 no C39 . C32 . H321 . 103.070 no C32 . C33 . C34 . 118.1(3) yes C32 . C33 . C38 . 123.4(3) yes C34 . C33 . C38 . 118.4(3) yes C33 . C34 . C35 . 120.7(3) yes C33 . C34 . H341 . 119.087 no C35 . C34 . H341 . 120.230 no C34 . C35 . C36 . 120.5(4) yes C34 . C35 . H351 . 118.163 no C36 . C35 . H351 . 121.167 no C35 . C36 . C37 . 119.5(4) yes C35 . C36 . H361 . 119.890 no C37 . C36 . H361 . 120.606 no C36 . C37 . C38 . 120.2(4) yes C36 . C37 . H371 . 120.870 no C38 . C37 . H371 . 118.901 no C33 . C38 . C37 . 120.7(4) yes C33 . C38 . H381 . 119.110 no C37 . C38 . H381 . 120.195 no C32 . C39 . H391 . 110.215 no C32 . C39 . H392 . 109.621 no H391 . C39 . H392 . 107.829 no C32 . C39 . H393 . 111.163 no H391 . C39 . H393 . 108.939 no H392 . C39 . H393 . 109.000 no N31 . C40 . C41 . 112.0(2) yes N31 . C40 . H401 . 109.726 no C41 . C40 . H401 . 108.978 no N31 . C40 . H402 . 109.467 no C41 . C40 . H402 . 109.345 no H401 . C40 . H402 . 107.211 no C40 . C41 . C42 . 121.1(3) yes C40 . C41 . C46 . 120.8(3) yes C42 . C41 . C46 . 118.1(3) yes C41 . C42 . C43 . 120.7(3) yes C41 . C42 . H421 . 118.360 no C43 . C42 . H421 . 120.952 no C42 . C43 . C44 . 120.5(3) yes C42 . C43 . H431 . 119.511 no C44 . C43 . H431 . 119.916 no C43 . C44 . C45 . 119.6(3) yes C43 . C44 . H441 . 119.081 no C45 . C44 . H441 . 121.339 no C44 . C45 . C46 . 120.6(4) yes C44 . C45 . H451 . 120.215 no C46 . C45 . H451 . 119.088 no C41 . C46 . C45 . 120.5(3) yes C41 . C46 . H461 . 118.033 no C45 . C46 . H461 . 121.479 no C30 . C47 . C48 . 105.57(19) yes C30 . C47 . C52 . 116.6(2) yes C48 . C47 . C52 . 114.1(2) yes C30 . C47 . H471 . 108.219 no C48 . C47 . H471 . 112.643 no C52 . C47 . H471 . 99.679 no C47 . C48 . N49 . 109.1(2) yes C47 . C48 . O51 . 125.5(2) yes N49 . C48 . O51 . 125.3(2) yes C48 . N49 . C50 . 114.8(2) yes C48 . N49 . H491 . 113.289 no C50 . N49 . H491 . 127.870 no C30 . C50 . N49 . 104.14(19) yes C30 . C50 . H501 . 111.367 no N49 . C50 . H501 . 111.310 no C30 . C50 . H502 . 110.599 no N49 . C50 . H502 . 111.710 no H501 . C50 . H502 . 107.753 no C47 . C52 . C53 . 116.76(19) yes C47 . C52 . H521 . 108.639 no C53 . C52 . H521 . 108.859 no C47 . C52 . H522 . 107.188 no C53 . C52 . H522 . 107.480 no H521 . C52 . H522 . 107.558 no C52 . C53 . C54 . 120.3(2) yes C52 . C53 . C58 . 121.0(3) yes C54 . C53 . C58 . 118.6(2) yes C53 . C54 . C55 . 120.3(3) yes C53 . C54 . H541 . 119.650 no C55 . C54 . H541 . 120.056 no C54 . C55 . C56 . 120.4(3) yes C54 . C55 . H551 . 119.692 no C56 . C55 . H551 . 119.927 no C55 . C56 . C57 . 120.2(3) yes C55 . C56 . H561 . 119.581 no C57 . C56 . H561 . 120.223 no C56 . C57 . C58 . 120.0(3) yes C56 . C57 . H571 . 121.050 no C58 . C57 . H571 . 118.986 no C53 . C58 . C57 . 120.5(3) yes C53 . C58 . H581 . 119.124 no C57 . C58 . H581 . 120.339 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