# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Steve Davies' _publ_contact_author_address ; Department of Organic Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road OXFORD OX1 3TA UNITED KINGDOM ; _publ_contact_author_email steve.davies@chem.ox.ac.uk _publ_contact_author_phone ' 01865 275 646' _publ_contact_author_fax ' 01865 275 633' loop_ _publ_author_name _publ_author_address S.G.Davies ;Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA ; A.C.Garner ;Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA ; E.C.Goddard ;Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA ; D.Kruchinin ;Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA ; P.M.Roberts ;Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA ; ; A.D.Smith ; ;Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA ; H.Rodriguez-Solla ;Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA ; _publ_section_title ; Lithium Amide Conjugate Addition for the Asymmetric Synthesis of 3-Aminopyrrolidines ; # 4281151 pr13 # 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_requested_category CO # choose from: FI FM FO CI CM CO AD# _publ_requested_coeditor_name 'Dr Paul Roberts' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 602326' _audit_creation_date 03-28-04 _audit_creation_method CRYSTALS_ver_12-03-99 #============================================================================== # 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 ; ? ; #========================================================================== _chemical_name_systematic # IUPAC name, in full ? _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment constr #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 17.1297(3) _cell_angle_alpha 90 _cell_length_b 8.2098(2) _cell_angle_beta 100.0736(8) _cell_length_c 19.4751(4) _cell_angle_gamma 90 _cell_volume 2696.6(1) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_int_tables_number 5 loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,y+1/2,z -x,y,-z -x+1/2,y+1/2,-z # 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 'C33 H34 N2 O1' _chemical_formula_moiety 'C33 H34 N2 O1' _chemical_compound_source ? _chemical_formula_weight 474.65 _cell_measurement_reflns_used 2964 _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 1.169 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1016.000 _exptl_absorpt_coefficient_mu 0.070 # 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 5704 _reflns_number_total 3244 _diffrn_reflns_av_R_equivalents 0.01 # Number of reflections with Friedels Law is 3244 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3070 _diffrn_reflns_theta_min 5.129 _diffrn_reflns_theta_max 27.424 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.218 _diffrn_measured_fraction_theta_full 0.984 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -22 _reflns_limit_h_max 21 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _refine_diff_density_min -0.12 _refine_diff_density_max 0.14 _refine_ls_number_reflns 2894 _refine_ls_number_parameters 325 #_refine_ls_R_factor_ref 0.0321 _refine_ls_wR_factor_ref 0.0325 _refine_ls_goodness_of_fit_ref 1.1889 #_reflns_number_all 3244 _refine_ls_R_factor_all 0.0373 _refine_ls_wR_factor_all 0.0350 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 2894 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_gt 0.0325 _refine_ls_shift/su_max 0.000475 _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 1.12 -0.692E-01 0.612 ; _diffrn_radiation_probe ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 COLLECT Software, Nonius BV 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_attached_hydrogens # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom C1 C 0.88581(8) 0.4025(2) 0.23901(7) 0.0270 1.0000 Uani . C2 C 0.81400(9) 0.2865(2) 0.22625(8) 0.0302 1.0000 Uani . C3 C 0.76738(9) 0.3216(2) 0.28392(8) 0.0326 1.0000 Uani . N4 N 0.80052(7) 0.44982(18) 0.32162(6) 0.0321 1.0000 Uani . C5 C 0.87012(9) 0.5188(2) 0.29845(8) 0.0322 1.0000 Uani . C6 C 0.7692(1) 0.5157(3) 0.38044(8) 0.0406 1.0000 Uani . C7 C 0.81670(9) 0.4711(2) 0.45124(8) 0.0349 1.0000 Uani . C8 C 0.86566(11) 0.3353(2) 0.46051(9) 0.0405 1.0000 Uani . C9 C 0.90476(12) 0.2921(3) 0.5268(1) 0.0512 1.0000 Uani . C10 C 0.89574(13) 0.3850(3) 0.58372(9) 0.0566 1.0000 Uani . C11 C 0.84790(14) 0.5211(3) 0.5752(1) 0.0589 1.0000 Uani . C12 C 0.80817(12) 0.5640(3) 0.50898(9) 0.0473 1.0000 Uani . O13 O 0.70803(7) 0.24845(18) 0.29368(7) 0.0464 1.0000 Uani . C14 C 0.8336(1) 0.1042(2) 0.22119(9) 0.0368 1.0000 Uani . C15 C 0.88386(11) 0.0333(2) 0.28598(9) 0.0370 1.0000 Uani . C16 C 0.96616(11) 0.0245(2) 0.2921(1) 0.0450 1.0000 Uani . C17 C 1.01270(13) -0.0470(3) 0.35000(12) 0.0562 1.0000 Uani . C18 C 0.97822(15) -0.1083(3) 0.40265(11) 0.0590 1.0000 Uani . C19 C 0.89743(15) -0.0978(3) 0.3993(1) 0.0573 1.0000 Uani . C20 C 0.84989(12) -0.0281(2) 0.3406(1) 0.0470 1.0000 Uani . N21 N 0.90010(7) 0.47554(17) 0.17354(6) 0.0275 1.0000 Uani . C22 C 0.98342(9) 0.5220(2) 0.17248(8) 0.0318 1.0000 Uani . C23 C 1.03335(9) 0.3684(2) 0.17447(8) 0.0309 1.0000 Uani . C24 C 1.10565(9) 0.3500(2) 0.21950(8) 0.0375 1.0000 Uani . C25 C 1.14853(11) 0.2052(3) 0.2198(1) 0.0483 1.0000 Uani . C26 C 1.12064(12) 0.0794(3) 0.17571(11) 0.0519 1.0000 Uani . C27 C 1.04962(11) 0.0979(3) 0.12937(11) 0.0501 1.0000 Uani . C28 C 1.0069(1) 0.2415(2) 0.12869(9) 0.0413 1.0000 Uani . C29 C 1.01640(11) 0.6492(2) 0.22679(11) 0.0450 1.0000 Uani . C30 C 0.84321(9) 0.6014(2) 0.14422(8) 0.0351 1.0000 Uani . C31 C 0.84301(9) 0.6235(2) 0.06703(9) 0.0387 1.0000 Uani . C32 C 0.83329(12) 0.4909(3) 0.02218(9) 0.0492 1.0000 Uani . C33 C 0.83552(13) 0.5099(4) -0.0485(1) 0.0646 1.0000 Uani . C34 C 0.84651(13) 0.6615(4) -0.07455(11) 0.0710 1.0000 Uani . C35 C 0.85458(15) 0.7956(4) -0.03109(14) 0.0738 1.0000 Uani . C36 C 0.85315(13) 0.7762(3) 0.04027(11) 0.0551 1.0000 Uani . H11 H 0.9381 0.3458 0.2562 0.0355 1.0000 Uiso . H21 H 0.7819 0.3092 0.1785 0.0373 1.0000 Uiso . H51 H 0.9164 0.5225 0.3376 0.0424 1.0000 Uiso . H52 H 0.8583 0.6319 0.2799 0.0424 1.0000 Uiso . H61 H 0.7673 0.6373 0.3758 0.0511 1.0000 Uiso . H62 H 0.7131 0.4743 0.3777 0.0511 1.0000 Uiso . H81 H 0.8735 0.2673 0.4186 0.0529 1.0000 Uiso . H91 H 0.9414 0.1934 0.5330 0.0636 1.0000 Uiso . H101 H 0.9242 0.3514 0.6324 0.0695 1.0000 Uiso . H111 H 0.8413 0.5899 0.6171 0.0739 1.0000 Uiso . H121 H 0.7722 0.6636 0.5034 0.0614 1.0000 Uiso . H141 H 0.8612 0.0877 0.1805 0.0460 1.0000 Uiso . H142 H 0.7815 0.0416 0.2117 0.0460 1.0000 Uiso . H161 H 0.9921 0.0719 0.2531 0.0548 1.0000 Uiso . H171 H 1.0722 -0.0523 0.3526 0.0721 1.0000 Uiso . H181 H 1.0121 -0.1629 0.4447 0.0710 1.0000 Uiso . H191 H 0.8695 -0.1409 0.4380 0.0709 1.0000 Uiso . H201 H 0.7910 -0.0191 0.3377 0.0594 1.0000 Uiso . H221 H 0.9851 0.5771 0.1268 0.0424 1.0000 Uiso . H241 H 1.1267 0.4431 0.2516 0.0486 1.0000 Uiso . H251 H 1.2003 0.1929 0.2533 0.0605 1.0000 Uiso . H261 H 1.1524 -0.0262 0.1776 0.0656 1.0000 Uiso . H271 H 1.0291 0.0077 0.0951 0.0647 1.0000 Uiso . H281 H 0.9553 0.2557 0.0939 0.0509 1.0000 Uiso . H291 H 1.0728 0.6763 0.2247 0.0552 1.0000 Uiso . H292 H 1.0144 0.6065 0.2757 0.0552 1.0000 Uiso . H293 H 0.9839 0.7521 0.2204 0.0552 1.0000 Uiso . H301 H 0.8578 0.7071 0.1697 0.0457 1.0000 Uiso . H302 H 0.7886 0.5688 0.1523 0.0457 1.0000 Uiso . H321 H 0.8247 0.3791 0.0419 0.0610 1.0000 Uiso . H331 H 0.8283 0.4123 -0.0810 0.0808 1.0000 Uiso . H341 H 0.8498 0.6741 -0.1254 0.0845 1.0000 Uiso . H351 H 0.8623 0.9085 -0.0507 0.0917 1.0000 Uiso . H361 H 0.8605 0.8769 0.0735 0.0713 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 0.0285(7) 0.0274(7) 0.0249(6) 0.0010(6) 0.0037(5) 0.0010(6) C2 0.0303(7) 0.0319(8) 0.0273(7) 0.0007(6) 0.0018(5) -0.0019(6) C3 0.0268(7) 0.0376(9) 0.0322(7) 0.0084(7) 0.0019(6) 0.0024(7) N4 0.0303(6) 0.0382(8) 0.0286(6) 0.0008(6) 0.0076(5) 0.0025(6) C5 0.0353(8) 0.0327(8) 0.0294(7) -0.0027(7) 0.0079(6) -0.0027(7) C6 0.0375(8) 0.0507(11) 0.0357(8) 0.0009(8) 0.0125(6) 0.0137(8) C7 0.0339(7) 0.0412(9) 0.0323(7) 0.0001(7) 0.0137(6) -0.0001(7) C8 0.0475(9) 0.042(1) 0.0334(8) -0.0004(8) 0.0110(7) 0.0071(8) C9 0.0538(11) 0.0593(13) 0.0406(9) 0.008(1) 0.0088(8) 0.009(1) C10 0.0559(11) 0.0826(16) 0.0310(9) 0.004(1) 0.0067(8) 0.0032(12) C11 0.0686(13) 0.0780(16) 0.0331(9) -0.013(1) 0.0174(9) 0.0022(13) C12 0.052(1) 0.0530(12) 0.0410(9) -0.0047(9) 0.0196(8) 0.0097(9) O13 0.0322(6) 0.0551(9) 0.0530(7) 0.0084(7) 0.0107(5) -0.0079(6) C14 0.0445(9) 0.0300(8) 0.0345(8) -0.0046(7) 0.0030(7) -0.0043(7) C15 0.0514(9) 0.0218(7) 0.0365(8) -0.0055(7) 0.0039(7) -0.0015(7) C16 0.051(1) 0.0349(9) 0.049(1) -0.0040(9) 0.0070(8) 0.0029(8) C17 0.0543(11) 0.0490(12) 0.0600(12) -0.0052(11) -0.0046(9) 0.007(1) C18 0.0760(15) 0.0469(12) 0.0466(11) -0.004(1) -0.010(1) 0.0067(11) C19 0.0881(16) 0.0409(11) 0.043(1) 0.0024(9) 0.012(1) -0.0027(11) C20 0.0621(11) 0.0325(9) 0.047(1) 0.0012(9) 0.0113(8) -0.0030(9) N21 0.0264(6) 0.0303(7) 0.0265(6) 0.0049(5) 0.0066(5) 0.0053(5) C22 0.0297(7) 0.0326(8) 0.0345(7) 0.0030(7) 0.0092(6) 0.0017(7) C23 0.0277(7) 0.0374(9) 0.0291(7) 0.0028(7) 0.0091(6) 0.0040(6) C24 0.0327(8) 0.050(1) 0.0305(7) -0.0011(8) 0.0064(6) 0.0065(8) C25 0.0370(9) 0.0676(13) 0.0394(9) 0.0031(9) 0.0042(7) 0.0199(9) C26 0.048(1) 0.0570(12) 0.0535(11) 0.001(1) 0.0153(8) 0.025(1) C27 0.045(1) 0.0507(11) 0.0561(11) -0.019(1) 0.0129(8) 0.0102(9) C28 0.0336(8) 0.0485(11) 0.0408(9) -0.0072(8) 0.0040(7) 0.0076(8) C29 0.0384(9) 0.034(1) 0.0630(11) -0.0065(9) 0.0112(8) -0.0049(8) C30 0.0344(8) 0.0363(9) 0.0359(8) 0.0081(7) 0.0096(6) 0.0098(7) C31 0.0272(7) 0.0518(11) 0.0374(8) 0.0156(8) 0.0068(6) 0.0083(7) C32 0.048(1) 0.0613(14) 0.0370(9) 0.0064(9) 0.0058(7) 0.005(1) C33 0.0536(11) 0.102(2) 0.037(1) 0.0052(12) 0.0043(8) 0.0158(13) C34 0.0531(12) 0.121(3) 0.0416(11) 0.0316(15) 0.0147(9) 0.0229(14) C35 0.0685(14) 0.090(2) 0.0665(15) 0.0475(15) 0.0234(12) 0.0112(14) C36 0.0547(11) 0.0582(13) 0.0545(11) 0.0234(11) 0.0152(9) 0.006(1) _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 . C2 . 1.541(2) yes C1 . C5 . 1.560(2) yes C1 . N21 . 1.4678(18) yes C1 . H11 . 1.013 no C2 . C3 . 1.515(2) yes C2 . C14 . 1.541(2) yes C2 . H21 . 1.012 no C3 . N4 . 1.350(2) yes C3 . O13 . 1.224(2) yes N4 . C5 . 1.461(2) yes N4 . C6 . 1.452(2) yes C5 . H51 . 1.000 no C5 . H52 . 1.004 no C6 . C7 . 1.518(2) yes C6 . H61 . 1.003 no C6 . H62 . 1.012 no C7 . C8 . 1.388(3) yes C7 . C12 . 1.387(2) yes C8 . C9 . 1.392(3) yes C8 . H81 . 1.018 no C9 . C10 . 1.377(3) yes C9 . H91 . 1.020 no C10 . C11 . 1.378(4) yes C10 . H101 . 1.024 no C11 . C12 . 1.393(3) yes C11 . H111 . 1.015 no C12 . H121 . 1.018 no C14 . C15 . 1.514(2) yes C14 . H141 . 1.001 no C14 . H142 . 1.018 no C15 . C16 . 1.396(3) yes C15 . C20 . 1.392(3) yes C16 . C17 . 1.391(3) yes C16 . H161 . 1.023 no C17 . C18 . 1.366(3) yes C17 . H171 . 1.013 no C18 . C19 . 1.377(3) yes C18 . H181 . 1.021 no C19 . C20 . 1.404(3) yes C19 . H191 . 1.024 no C20 . H201 . 1.003 no N21 . C22 . 1.4810(19) yes N21 . C30 . 1.466(2) yes C22 . C23 . 1.520(2) yes C22 . C29 . 1.523(2) yes C22 . H221 . 1.004 no C23 . C24 . 1.395(2) yes C23 . C28 . 1.394(2) yes C24 . C25 . 1.397(3) yes C24 . H241 . 1.013 no C25 . C26 . 1.374(3) yes C25 . H251 . 1.010 no C26 . C27 . 1.390(3) yes C26 . H261 . 1.020 no C27 . C28 . 1.387(3) yes C27 . H271 . 1.018 no C28 . H281 . 1.022 no C29 . H291 . 0.999 no C29 . H292 . 1.022 no C29 . H293 . 1.007 no C30 . C31 . 1.514(2) yes C30 . H301 . 1.009 no C30 . H302 . 1.011 no C31 . C32 . 1.387(3) yes C31 . C36 . 1.380(3) yes C32 . C33 . 1.393(3) yes C32 . H321 . 1.016 no C33 . C34 . 1.369(4) yes C33 . H331 . 1.015 no C34 . C35 . 1.380(4) yes C34 . H341 . 1.007 no C35 . C36 . 1.403(3) yes C35 . H351 . 1.020 no C36 . H361 . 1.044 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 . C5 . 105.17(11) yes C2 . C1 . N21 . 111.22(11) yes C5 . C1 . N21 . 118.11(13) yes C2 . C1 . H11 . 113.827 no C5 . C1 . H11 . 107.008 no N21 . C1 . H11 . 101.747 no C1 . C2 . C3 . 105.80(12) yes C1 . C2 . C14 . 115.70(13) yes C3 . C2 . C14 . 112.40(13) yes C1 . C2 . H21 . 108.950 no C3 . C2 . H21 . 111.993 no C14 . C2 . H21 . 102.096 no C2 . C3 . N4 . 108.98(13) yes C2 . C3 . O13 . 125.55(16) yes N4 . C3 . O13 . 125.44(15) yes C3 . N4 . C5 . 114.99(13) yes C3 . N4 . C6 . 122.73(14) yes C5 . N4 . C6 . 122.27(14) yes C1 . C5 . N4 . 104.35(12) yes C1 . C5 . H51 . 111.619 no N4 . C5 . H51 . 110.930 no C1 . C5 . H52 . 110.461 no N4 . C5 . H52 . 110.243 no H51 . C5 . H52 . 109.178 no N4 . C6 . C7 . 114.41(13) yes N4 . C6 . H61 . 108.039 no C7 . C6 . H61 . 109.010 no N4 . C6 . H62 . 108.241 no C7 . C6 . H62 . 108.666 no H61 . C6 . H62 . 108.322 no C6 . C7 . C8 . 121.82(15) yes C6 . C7 . C12 . 119.21(16) yes C8 . C7 . C12 . 118.90(16) yes C7 . C8 . C9 . 120.46(17) yes C7 . C8 . H81 . 119.886 no C9 . C8 . H81 . 119.652 no C8 . C9 . C10 . 120.1(2) yes C8 . C9 . H91 . 119.906 no C10 . C9 . H91 . 119.936 no C9 . C10 . C11 . 120.00(18) yes C9 . C10 . H101 . 119.529 no C11 . C10 . H101 . 120.469 no C10 . C11 . C12 . 120.06(18) yes C10 . C11 . H111 . 120.057 no C12 . C11 . H111 . 119.887 no C7 . C12 . C11 . 120.46(19) yes C7 . C12 . H121 . 120.143 no C11 . C12 . H121 . 119.397 no C2 . C14 . C15 . 114.75(14) yes C2 . C14 . H141 . 108.671 no C15 . C14 . H141 . 109.228 no C2 . C14 . H142 . 107.950 no C15 . C14 . H142 . 108.080 no H141 . C14 . H142 . 107.956 no C14 . C15 . C16 . 120.68(16) yes C14 . C15 . C20 . 121.52(17) yes C16 . C15 . C20 . 117.79(17) yes C15 . C16 . C17 . 121.25(18) yes C15 . C16 . H161 . 118.690 no C17 . C16 . H161 . 120.060 no C16 . C17 . C18 . 120.1(2) yes C16 . C17 . H171 . 119.206 no C18 . C17 . H171 . 120.679 no C17 . C18 . C19 . 120.3(2) yes C17 . C18 . H181 . 120.334 no C19 . C18 . H181 . 119.389 no C18 . C19 . C20 . 119.95(19) yes C18 . C19 . H191 . 122.615 no C20 . C19 . H191 . 117.431 no C15 . C20 . C19 . 120.59(19) yes C15 . C20 . H201 . 118.782 no C19 . C20 . H201 . 120.613 no C1 . N21 . C22 . 115.14(11) yes C1 . N21 . C30 . 115.21(11) yes C22 . N21 . C30 . 112.94(13) yes N21 . C22 . C23 . 108.99(13) yes N21 . C22 . C29 . 114.08(13) yes C23 . C22 . C29 . 114.36(13) yes N21 . C22 . H221 . 107.832 no C23 . C22 . H221 . 107.040 no C29 . C22 . H221 . 103.995 no C22 . C23 . C24 . 122.65(15) yes C22 . C23 . C28 . 119.00(14) yes C24 . C23 . C28 . 118.33(15) yes C23 . C24 . C25 . 120.22(17) yes C23 . C24 . H241 . 119.199 no C25 . C24 . H241 . 120.584 no C24 . C25 . C26 . 120.78(16) yes C24 . C25 . H251 . 119.317 no C26 . C25 . H251 . 119.894 no C25 . C26 . C27 . 119.51(18) yes C25 . C26 . H261 . 119.400 no C27 . C26 . H261 . 121.085 no C26 . C27 . C28 . 119.97(19) yes C26 . C27 . H271 . 120.634 no C28 . C27 . H271 . 119.388 no C23 . C28 . C27 . 121.14(15) yes C23 . C28 . H281 . 118.999 no C27 . C28 . H281 . 119.863 no C22 . C29 . H291 . 111.567 no C22 . C29 . H292 . 110.086 no H291 . C29 . H292 . 107.837 no C22 . C29 . H293 . 111.018 no H291 . C29 . H293 . 109.004 no H292 . C29 . H293 . 107.177 no N21 . C30 . C31 . 110.93(13) yes N21 . C30 . H301 . 108.938 no C31 . C30 . H301 . 110.044 no N21 . C30 . H302 . 108.793 no C31 . C30 . H302 . 110.194 no H301 . C30 . H302 . 107.873 no C30 . C31 . C32 . 120.70(17) yes C30 . C31 . C36 . 120.34(18) yes C32 . C31 . C36 . 118.96(17) yes C31 . C32 . C33 . 120.9(2) yes C31 . C32 . H321 . 118.711 no C33 . C32 . H321 . 120.389 no C32 . C33 . C34 . 119.8(3) yes C32 . C33 . H331 . 120.368 no C34 . C33 . H331 . 119.836 no C33 . C34 . C35 . 120.22(19) yes C33 . C34 . H341 . 119.474 no C35 . C34 . H341 . 120.294 no C34 . C35 . C36 . 120.0(2) yes C34 . C35 . H351 . 120.075 no C36 . C35 . H351 . 119.943 no C31 . C36 . C35 . 120.1(2) yes C31 . C36 . H361 . 119.692 no C35 . C36 . H361 . 120.169 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