Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Steve Davies' _publ_contact_author_address ;Chemistry Research Laboraotory Mansfield Road Oxford OX1 3TA ; _publ_contact_author_email steve.davies@chemistry.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 ; P.M.Roberts ;Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA ; A.D.Smith ;Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA ; M.J.Sweet ;Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA ; ; J.E.Thomson ; ;Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA ; _publ_section_title ; Oxazinanones as Chiral Auxiliaries: Synthesis and Evaluation in Enolate Alkylations and Aldol Reactions ; data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 280051' _audit_creation_date 03-12-05 _audit_creation_method CRYSTALS_ver_12-03-99 _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 '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 5.9454(2) _cell_angle_alpha 90 _cell_length_b 8.1078(3) _cell_angle_beta 90 _cell_length_c 18.0676(6) _cell_angle_gamma 90 _cell_volume 870.93(5) _symmetry_cell_setting 'Orthorhombic ' _symmetry_space_group_name_H-M 'P 21 21 21 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C10 H11 N1 O2 ' _chemical_formula_moiety ' C10 H11 N1 O2 ' _chemical_compound_source ; ? ; _chemical_formula_weight 177.20 _cell_measurement_reflns_used 1136 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 190 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 376.000 _exptl_absorpt_coefficient_mu 0.095 # Sheldrick geometric definitions 0.99 1.00 _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 1.00 _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 1966 _reflns_number_total 1167 _diffrn_reflns_av_R_equivalents 0.01 # Number of reflections with Friedels Law is 1167 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 996 _diffrn_reflns_theta_min 5.167 _diffrn_reflns_theta_max 27.469 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.126 _diffrn_measured_fraction_theta_full 0.986 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min 0 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _refine_diff_density_min -0.13 _refine_diff_density_max 0.17 _refine_ls_number_reflns 1056 _refine_ls_number_parameters 118 #_refine_ls_R_factor_ref 0.0280 _refine_ls_wR_factor_ref 0.0326 _refine_ls_goodness_of_fit_ref 1.0885 #_reflns_number_all 1167 _refine_ls_R_factor_all 0.0317 _refine_ls_wR_factor_all 0.0361 # 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 1056 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_gt 0.0326 _refine_ls_shift/su_max 0.000493 _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 0.792 0.266 0.394 ; _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 -0.2353(2) 0.05836(17) -0.88061(8) 0.0232 1.0000 Uani . C2 C -0.2483(2) -0.12751(17) -0.89226(7) 0.0212 1.0000 Uani . C3 C -0.4451(3) -0.2081(2) -0.87064(8) 0.0274 1.0000 Uani . C4 C -0.4687(3) -0.37718(19) -0.88066(8) 0.0306 1.0000 Uani . C5 C -0.2952(3) -0.46739(18) -0.91205(8) 0.0302 1.0000 Uani . C6 C -0.0990(3) -0.38925(19) -0.93351(8) 0.0287 1.0000 Uani . C7 C -0.0755(3) -0.21851(17) -0.92382(8) 0.0245 1.0000 Uani . N8 N -0.0530(2) 0.13509(14) -0.92265(6) 0.0236 1.0000 Uani . C9 C 0.1398(2) 0.19503(17) -0.89593(8) 0.0236 1.0000 Uani . O10 O 0.18796(19) 0.17340(16) -0.82354(6) 0.0354 1.0000 Uani . C11 C 0.0373(3) 0.0758(2) -0.77831(8) 0.0345 1.0000 Uani . H11 H -0.3844 0.1017 -0.8999 0.0287 1.0000 Uiso . C12 C -0.2038(3) 0.1044(2) -0.79952(8) 0.0315 1.0000 Uani . O13 O 0.27914(19) 0.26922(14) -0.93345(6) 0.0335 1.0000 Uani . H31 H -0.5717 -0.1426 -0.8476 0.0349 1.0000 Uiso . H41 H -0.6099 -0.4338 -0.8646 0.0367 1.0000 Uiso . H51 H -0.3158 -0.5889 -0.9196 0.0381 1.0000 Uiso . H61 H 0.0270 -0.4544 -0.9566 0.0348 1.0000 Uiso . H71 H 0.0667 -0.1605 -0.9403 0.0300 1.0000 Uiso . H81 H -0.0805 0.1642 -0.9707 0.0500 1.0000 Uiso . H111 H 0.0731 -0.0447 -0.7852 0.0409 1.0000 Uiso . H112 H 0.0597 0.1046 -0.7247 0.0409 1.0000 Uiso . H121 H -0.2421 0.2253 -0.7920 0.0388 1.0000 Uiso . H122 H -0.3068 0.0372 -0.7676 0.0388 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 0.0192(6) 0.0231(6) 0.0273(6) 0.0009(5) 0.0008(5) 0.0002(6) C2 0.0219(7) 0.0225(6) 0.0192(6) 0.0014(5) -0.0018(5) -0.0003(5) C3 0.0234(7) 0.0307(7) 0.0282(7) -0.0020(6) 0.0020(6) -0.0016(6) C4 0.0309(8) 0.0314(8) 0.0295(7) 0.0031(6) -0.0011(6) -0.0106(7) C5 0.0410(9) 0.0234(6) 0.0264(6) -0.0005(5) -0.0071(7) -0.0023(7) C6 0.0334(8) 0.0265(7) 0.0263(7) -0.0015(6) -0.0008(6) 0.0061(6) C7 0.0230(7) 0.0268(7) 0.0237(6) 0.0015(5) 0.0004(6) 0.0018(6) N8 0.0269(6) 0.0235(5) 0.0203(5) 0.0031(4) -0.0003(5) -0.0032(5) C9 0.0244(7) 0.0218(6) 0.0246(6) 0.0008(6) 0.0008(6) 0.0016(6) O10 0.0308(6) 0.0490(7) 0.0265(5) 0.0059(5) -0.0064(5) -0.0102(6) C11 0.046(1) 0.0376(8) 0.0200(6) 0.0032(6) -0.0017(7) -0.0057(8) C12 0.0359(8) 0.0305(7) 0.0279(7) -0.0066(6) 0.0110(7) -0.0048(7) O13 0.0303(6) 0.0350(6) 0.0353(5) 0.0048(5) 0.0054(5) -0.0074(5) _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 . 1.5236(19) yes C1 . N8 . 1.4623(18) yes C1 . H11 . 1.016 no C1 . C12 . 1.524(2) yes C2 . C3 . 1.396(2) yes C2 . C7 . 1.387(2) yes C3 . C4 . 1.390(2) yes C3 . H31 . 1.011 no C4 . C5 . 1.386(2) yes C4 . H41 . 1.000 no C5 . C6 . 1.383(2) yes C5 . H51 . 1.002 no C6 . C7 . 1.402(2) yes C6 . H61 . 1.007 no C7 . H71 . 1.013 no N8 . C9 . 1.3355(19) yes N8 . H81 . 0.914 no C9 . O10 . 1.3504(17) yes C9 . O13 . 1.2277(17) yes O10 . C11 . 1.448(2) yes C11 . C12 . 1.502(3) yes C11 . H111 . 1.007 no C11 . H112 . 1.006 no C12 . H121 . 1.015 no C12 . H122 . 1.002 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 . N8 . 112.74(12) yes C2 . C1 . H11 . 104.528 no N8 . C1 . H11 . 108.740 no C2 . C1 . C12 . 112.44(11) yes N8 . C1 . C12 . 107.71(11) yes H11 . C1 . C12 . 110.643 no C1 . C2 . C3 . 117.82(13) yes C1 . C2 . C7 . 123.06(13) yes C3 . C2 . C7 . 119.12(13) yes C2 . C3 . C4 . 120.66(15) yes C2 . C3 . H31 . 119.564 no C4 . C3 . H31 . 119.779 no C3 . C4 . C5 . 119.91(15) yes C3 . C4 . H41 . 120.000 no C5 . C4 . H41 . 120.087 no C4 . C5 . C6 . 120.06(13) yes C4 . C5 . H51 . 118.891 no C6 . C5 . H51 . 121.041 no C5 . C6 . C7 . 120.07(15) yes C5 . C6 . H61 . 120.221 no C7 . C6 . H61 . 119.709 no C2 . C7 . C6 . 120.19(15) yes C2 . C7 . H71 . 119.470 no C6 . C7 . H71 . 120.335 no C1 . N8 . C9 . 127.10(12) yes C1 . N8 . H81 . 118.059 no C9 . N8 . H81 . 113.756 no N8 . C9 . O10 . 119.00(12) yes N8 . C9 . O13 . 123.91(13) yes O10 . C9 . O13 . 117.09(13) yes C9 . O10 . C11 . 119.12(12) yes O10 . C11 . C12 . 111.21(13) yes O10 . C11 . H111 . 109.275 no C12 . C11 . H111 . 108.656 no O10 . C11 . H112 . 109.576 no C12 . C11 . H112 . 109.635 no H111 . C11 . H112 . 108.436 no C1 . C12 . C11 . 108.94(13) yes C1 . C12 . H121 . 109.777 no C11 . C12 . H121 . 109.197 no C1 . C12 . H122 . 110.150 no C11 . C12 . H122 . 110.627 no H121 . C12 . H122 . 108.132 no # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # Attachment 'CCDC280052.cif' data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 280052' _audit_creation_date 03-19-05 _audit_creation_method CRYSTALS_ver_12-03-99 _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 '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 9.2401(1) _cell_angle_alpha 90 _cell_length_b 10.5810(1) _cell_angle_beta 90 _cell_length_c 46.9695(5) _cell_angle_gamma 90 _cell_volume 4592.18(8) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 16 _chemical_formula_sum 'C12 H15 N1 O2' _chemical_formula_moiety 'C12 H15 N1 O2' _chemical_compound_source ? _chemical_formula_weight 205.26 _cell_measurement_reflns_used 5424 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 100 _exptl_crystal_description ' block ' _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1760.000 _exptl_absorpt_coefficient_mu 0.081 # Sheldrick geometric definitions 0.99 0.99 _diffrn_measurement_device_type ; Enraf Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; USER DEFINED STRUCTURE SOLUTION ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 190 _diffrn_reflns_number 9870 _reflns_number_total 5748 _diffrn_reflns_av_R_equivalents 0.02 # Number of reflections with Friedels Law is 5748 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5281 _diffrn_reflns_theta_min 5.119 _diffrn_reflns_theta_max 27.511 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 26.755 _diffrn_measured_fraction_theta_full 0.972 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -60 _diffrn_reflns_limit_l_max 61 _reflns_limit_h_min 0 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 60 _refine_diff_density_min -0.23 _refine_diff_density_max 0.21 _refine_ls_number_reflns 4682 _refine_ls_number_parameters 541 #_refine_ls_R_factor_ref 0.0667 _refine_ls_wR_factor_ref 0.0478 _refine_ls_goodness_of_fit_ref 1.0322 #_reflns_number_all 5748 _refine_ls_R_factor_all 0.0896 _refine_ls_wR_factor_all 0.0607 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>0.50u(I) _reflns_number_gt 4682 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_gt 0.0478 _refine_ls_shift/su_max 0.000563 _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 0.929 0.463 0.805 0.217 0.185 ; _diffrn_radiation_probe ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; User-defined structure solution reference COLLECT Software, Nonius BV 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_attached_hydrogens # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom C1 C -0.0854(3) -0.4011(3) -0.51401(6) 0.0405 1.0000 Uani . C2 C 0.0255(4) -0.3250(3) -0.53028(6) 0.0504 1.0000 Uani . C3 C 0.1664(4) -0.3707(4) -0.53371(8) 0.0689 1.0000 Uani . C4 C 0.2677(5) -0.3056(6) -0.5491(1) 0.0926 1.0000 Uani . C5 C 0.2322(7) -0.1938(7) -0.56168(9) 0.0972 1.0000 Uani . C6 C 0.0940(7) -0.1427(5) -0.55841(8) 0.0926 1.0000 Uani . C7 C -0.0115(5) -0.2100(4) -0.54238(7) 0.0663 1.0000 Uani . C8 C -0.1230(3) -0.5244(3) -0.52901(6) 0.0446 1.0000 Uani . C9 C -0.2125(3) -0.6096(3) -0.51023(6) 0.0450 1.0000 Uani . O10 O -0.1356(3) -0.6291(2) -0.48303(4) 0.0548 1.0000 Uani . C11 C -0.0574(3) -0.5358(3) -0.47119(6) 0.0407 1.0000 Uani . H11 H -0.1774 -0.3481 -0.5127 0.0537 1.0000 Uiso . N12 N -0.0301(3) -0.4314(2) -0.48594(5) 0.0404 1.0000 Uani . O13 O -0.0122(3) -0.5535(2) -0.44679(4) 0.0515 1.0000 Uani . C14 C -0.3600(4) -0.5539(4) -0.50360(8) 0.0631 1.0000 Uani . C15 C -0.2273(4) -0.7413(4) -0.52248(8) 0.0619 1.0000 Uani . C16 C 0.2367(3) -0.8719(3) -0.63292(6) 0.0439 1.0000 Uani . C17 C 0.2859(3) -0.9863(3) -0.64961(6) 0.0425 1.0000 Uani . C18 C 0.3699(4) -0.9761(3) -0.67396(7) 0.0496 1.0000 Uani . C19 C 0.4199(4) -1.0843(4) -0.68763(7) 0.0572 1.0000 Uani . C20 C 0.3869(4) -1.2029(4) -0.67723(9) 0.0613 1.0000 Uani . C21 C 0.3034(5) -1.2135(3) -0.65336(9) 0.0609 1.0000 Uani . C22 C 0.2516(4) -1.1062(3) -0.63964(7) 0.0550 1.0000 Uani . C23 C 0.3562(4) -0.8242(3) -0.61330(6) 0.0462 1.0000 Uani . C24 C 0.3143(4) -0.7013(3) -0.59904(6) 0.0501 1.0000 Uani . O25 O 0.2749(3) -0.6087(2) -0.62124(5) 0.0619 1.0000 Uani . C26 C 0.2071(4) -0.6442(4) -0.64525(6) 0.0528 1.0000 Uani . N27 N 0.1948(3) -0.7679(3) -0.65150(5) 0.0454 1.0000 Uani . O28 O 0.1625(3) -0.5603(2) -0.66098(4) 0.0630 1.0000 Uani . C29 C 0.4410(4) -0.6422(4) -0.58368(8) 0.0639 1.0000 Uani . C30 C 0.1852(4) -0.7132(4) -0.57922(7) 0.0679 1.0000 Uani . C31 C 0.6876(3) -1.1170(3) -0.61626(6) 0.0391 1.0000 Uani . H31 H 0.1934 -0.4583 -0.5245 0.0885 1.0000 Uiso . C32 C 0.7269(3) -0.9804(3) -0.62211(6) 0.0398 1.0000 Uani . C33 C 0.7370(4) -0.9437(3) -0.65061(6) 0.0483 1.0000 Uani . C34 C 0.7845(4) -0.8243(3) -0.65768(7) 0.0557 1.0000 Uani . C35 C 0.8200(4) -0.7391(3) -0.63695(8) 0.0574 1.0000 Uani . C36 C 0.8076(4) -0.7733(3) -0.60876(8) 0.0565 1.0000 Uani . C37 C 0.7626(4) -0.8941(3) -0.60120(7) 0.0465 1.0000 Uani . C38 C 0.8193(4) -1.2003(3) -0.62100(6) 0.0423 1.0000 Uani . C39 C 0.7909(4) -1.3367(3) -0.61306(6) 0.0429 1.0000 Uani . O40 O 0.7314(2) -1.3411(2) -0.58409(4) 0.0483 1.0000 Uani . C41 C 0.6584(3) -1.2444(3) -0.57230(6) 0.0420 1.0000 Uani . H41 H 0.3724 -0.3422 -0.5513 0.1167 1.0000 Uiso . N42 N 0.6392(3) -1.1378(2) -0.58700(5) 0.0417 1.0000 Uani . O43 O 0.6156(2) -1.2591(2) -0.54787(4) 0.0515 1.0000 Uani . C44 C 0.9309(4) -1.4105(3) -0.61140(7) 0.0542 1.0000 Uani . C45 C 0.6808(5) -1.3991(3) -0.63231(8) 0.0625 1.0000 Uani . C46 C 0.1750(3) -0.5258(3) -0.74007(6) 0.0411 1.0000 Uani . C47 C 0.3293(4) -0.4847(3) -0.73481(7) 0.0441 1.0000 Uani . C48 C 0.4204(4) -0.5434(4) -0.71575(8) 0.0568 1.0000 Uani . C49 C 0.5649(4) -0.5054(4) -0.7129(1) 0.0713 1.0000 Uani . C50 C 0.6177(5) -0.4090(5) -0.72940(12) 0.0810 1.0000 Uani . C51 C 0.5274(6) -0.3471(4) -0.74770(11) 0.0795 1.0000 Uani . H51 H 0.3061 -0.1452 -0.5723 0.1177 1.0000 Uiso . C52 C 0.3837(5) -0.3838(4) -0.75074(8) 0.0631 1.0000 Uani . C53 C 0.1575(3) -0.5820(3) -0.76959(6) 0.0452 1.0000 Uani . C54 C 0.0224(4) -0.6620(3) -0.77212(7) 0.0458 1.0000 Uani . O55 O 0.0350(2) -0.7639(2) -0.75092(4) 0.0434 1.0000 Uani . C56 C 0.0663(3) -0.7301(3) -0.72373(6) 0.0398 1.0000 Uani . N57 N 0.1270(3) -0.6182(2) -0.71905(5) 0.0425 1.0000 Uani . O58 O 0.0382(3) -0.8063(2) -0.70490(4) 0.0508 1.0000 Uani . C59 C 0.0143(5) -0.7304(4) -0.80050(7) 0.0651 1.0000 Uani . C60 C -0.1170(4) -0.5898(4) -0.76594(8) 0.0593 1.0000 Uani . H61 H 0.0711 -0.0598 -0.5679 0.1107 1.0000 Uiso . H71 H -0.1135 -0.1704 -0.5390 0.0849 1.0000 Uiso . H81 H -0.1773 -0.5045 -0.5471 0.0526 1.0000 Uiso . H82 H -0.0291 -0.5668 -0.5344 0.0526 1.0000 Uiso . H121 H 0.0225 -0.3584 -0.4790 0.0500 1.0000 Uiso . H141 H -0.4179 -0.6108 -0.4908 0.0792 1.0000 Uiso . H142 H -0.4167 -0.5382 -0.5215 0.0792 1.0000 Uiso . H143 H -0.3492 -0.4690 -0.4934 0.0792 1.0000 Uiso . H151 H -0.2857 -0.7975 -0.5097 0.0806 1.0000 Uiso . H152 H -0.2746 -0.7387 -0.5418 0.0806 1.0000 Uiso . H153 H -0.1280 -0.7819 -0.5250 0.0806 1.0000 Uiso . H161 H 0.1498 -0.8984 -0.6211 0.0559 1.0000 Uiso . H181 H 0.3959 -0.8899 -0.6816 0.0583 1.0000 Uiso . H191 H 0.4823 -1.0764 -0.7053 0.0718 1.0000 Uiso . H201 H 0.4199 -1.2799 -0.6880 0.0732 1.0000 Uiso . H211 H 0.2839 -1.3005 -0.6445 0.0727 1.0000 Uiso . H221 H 0.1857 -1.1158 -0.6220 0.0705 1.0000 Uiso . H231 H 0.4468 -0.8111 -0.6252 0.0587 1.0000 Uiso . H232 H 0.3787 -0.8906 -0.5986 0.0587 1.0000 Uiso . H271 H 0.1371 -0.7775 -0.6696 0.0500 1.0000 Uiso . H291 H 0.4141 -0.5623 -0.5742 0.0799 1.0000 Uiso . H292 H 0.5233 -0.6254 -0.5976 0.0799 1.0000 Uiso . H293 H 0.4807 -0.7032 -0.5687 0.0799 1.0000 Uiso . H301 H 0.1591 -0.6292 -0.5703 0.0837 1.0000 Uiso . H302 H 0.0954 -0.7425 -0.5903 0.0837 1.0000 Uiso . H303 H 0.2018 -0.7759 -0.5636 0.0837 1.0000 Uiso . H311 H 0.6053 -1.1413 -0.6294 0.0496 1.0000 Uiso . H331 H 0.7137 -1.0075 -0.6662 0.0621 1.0000 Uiso . H341 H 0.7882 -0.7985 -0.6787 0.0702 1.0000 Uiso . H351 H 0.8568 -0.6522 -0.6427 0.0756 1.0000 Uiso . H361 H 0.8343 -0.7115 -0.5931 0.0739 1.0000 Uiso . H371 H 0.7546 -0.9168 -0.5804 0.0545 1.0000 Uiso . H381 H 0.8498 -1.1946 -0.6416 0.0535 1.0000 Uiso . H382 H 0.9023 -1.1651 -0.6091 0.0535 1.0000 Uiso . H421 H 0.5636 -1.0675 -0.5819 0.0500 1.0000 Uiso . H441 H 0.9108 -1.5010 -0.6057 0.0638 1.0000 Uiso . H442 H 0.9819 -1.4097 -0.6299 0.0638 1.0000 Uiso . H443 H 0.9965 -1.3725 -0.5963 0.0638 1.0000 Uiso . H451 H 0.6601 -1.4883 -0.6264 0.0808 1.0000 Uiso . H452 H 0.7122 -1.3976 -0.6526 0.0808 1.0000 Uiso . H453 H 0.5837 -1.3508 -0.6312 0.0808 1.0000 Uiso . H461 H 0.1097 -0.4499 -0.7388 0.0499 1.0000 Uiso . H481 H 0.3829 -0.6188 -0.7034 0.0701 1.0000 Uiso . H491 H 0.6309 -0.5501 -0.6982 0.0910 1.0000 Uiso . H501 H 0.7227 -0.3817 -0.7279 0.0956 1.0000 Uiso . H511 H 0.5670 -0.2745 -0.7600 0.1016 1.0000 Uiso . H521 H 0.3157 -0.3337 -0.7643 0.0778 1.0000 Uiso . H531 H 0.1554 -0.5132 -0.7840 0.0590 1.0000 Uiso . H532 H 0.2444 -0.6382 -0.7735 0.0590 1.0000 Uiso . H571 H 0.1479 -0.5947 -0.7002 0.0500 1.0000 Uiso . H591 H -0.0779 -0.7837 -0.8016 0.0784 1.0000 Uiso . H592 H 0.0151 -0.6713 -0.8169 0.0784 1.0000 Uiso . H593 H 0.0986 -0.7915 -0.8025 0.0784 1.0000 Uiso . H601 H -0.2031 -0.6459 -0.7683 0.0736 1.0000 Uiso . H602 H -0.1270 -0.5166 -0.7800 0.0736 1.0000 Uiso . H603 H -0.1151 -0.5541 -0.7463 0.0736 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 0.0385(16) 0.0549(19) 0.0281(14) 0.0025(14) -0.0039(12) -0.0057(15) C2 0.054(2) 0.068(2) 0.0291(15) -0.0050(15) -0.0042(15) -0.0234(19) C3 0.055(2) 0.100(3) 0.052(2) -0.008(2) 0.0061(17) -0.025(2) C4 0.080(3) 0.133(5) 0.065(3) -0.016(3) 0.013(2) -0.052(3) C5 0.100(4) 0.145(5) 0.047(2) -0.016(3) 0.001(3) -0.078(4) C6 0.145(5) 0.095(3) 0.038(2) 0.015(2) -0.027(3) -0.064(4) C7 0.090(3) 0.063(2) 0.0452(19) 0.0078(18) -0.022(2) -0.034(2) C8 0.0420(17) 0.0550(19) 0.0368(16) -0.0001(14) -0.0034(14) -0.0041(16) C9 0.0449(17) 0.0553(19) 0.0348(15) -0.0041(14) -0.0107(14) -0.0047(16) O10 0.0674(15) 0.0555(14) 0.0415(12) 0.005(1) -0.0129(11) -0.0159(13) C11 0.0393(16) 0.0491(18) 0.0338(15) -0.0046(14) -0.0015(13) -0.0036(15) N12 0.0445(14) 0.0449(14) 0.0317(12) 0.0011(11) -0.0038(11) -0.0051(13) O13 0.0639(15) 0.0581(14) 0.0325(11) 0.004(1) -0.012(1) -0.0073(13) C14 0.047(2) 0.078(3) 0.064(2) -0.004(2) 0.0063(17) -0.009(2) C15 0.070(2) 0.059(2) 0.057(2) -0.0046(17) -0.0166(18) -0.009(2) C16 0.0409(17) 0.0543(19) 0.0365(15) 0.0043(14) -0.0014(14) 0.0046(16) C17 0.0404(17) 0.0493(19) 0.0376(16) -0.0028(14) -0.0058(14) 0.0049(16) C18 0.0469(19) 0.057(2) 0.0450(18) -0.0020(16) -0.0001(15) 0.0030(18) C19 0.051(2) 0.073(3) 0.049(2) -0.0152(18) -0.0051(16) 0.013(2) C20 0.060(2) 0.061(2) 0.063(2) -0.0184(19) -0.021(2) 0.016(2) C21 0.066(2) 0.048(2) 0.069(2) 0.0010(18) -0.025(2) 0.0044(19) C22 0.060(2) 0.059(2) 0.0464(18) 0.0087(17) -0.0092(17) -0.003(2) C23 0.0487(18) 0.0522(19) 0.0378(16) -0.0034(14) -0.0026(14) 0.0060(17) C24 0.055(2) 0.065(2) 0.0307(15) -0.0033(15) -0.0056(14) 0.0121(18) O25 0.0907(19) 0.0568(14) 0.0382(12) -0.0061(11) -0.0098(13) 0.0171(15) C26 0.061(2) 0.069(2) 0.0288(16) -0.0040(15) 0.0039(15) 0.017(2) N27 0.0501(16) 0.0502(17) 0.0358(13) -0.0020(12) -0.0089(12) 0.0082(14) O28 0.099(2) 0.0543(14) 0.0355(12) -0.0019(11) -0.0052(13) 0.0224(15) C29 0.067(2) 0.067(2) 0.058(2) -0.0165(19) -0.0146(18) 0.003(2) C30 0.067(2) 0.097(3) 0.0403(18) -0.0156(19) 0.0020(17) 0.014(2) C31 0.0409(16) 0.0422(17) 0.0341(15) -0.0034(13) 0.0014(13) -0.0039(14) C32 0.0321(15) 0.0451(17) 0.0421(16) -0.0038(14) 0.0047(13) 0.0024(14) C33 0.060(2) 0.0465(19) 0.0384(16) -0.0033(14) 0.0063(15) 0.0005(17) C34 0.065(2) 0.056(2) 0.0468(19) 0.0076(16) 0.0162(17) -0.0015(19) C35 0.060(2) 0.0456(19) 0.067(2) 0.0010(18) 0.0200(19) -0.0060(19) C36 0.058(2) 0.047(2) 0.064(2) -0.0140(17) 0.0063(18) -0.0100(18) C37 0.0482(18) 0.0495(19) 0.0417(16) -0.0050(15) 0.0032(15) -0.0014(17) C38 0.0488(18) 0.0415(17) 0.0366(15) -0.0077(13) 0.0060(14) -0.0014(15) C39 0.0510(19) 0.0456(18) 0.0321(15) -0.0060(13) 0.0036(14) 0.0019(16) O40 0.0557(14) 0.0471(13) 0.0422(11) 0.001(1) 0.011(1) 0.0082(12) C41 0.0354(16) 0.0497(19) 0.0408(17) -0.0009(15) 0.0020(13) 0.0023(15) N42 0.0452(14) 0.0446(14) 0.0354(13) 0.0052(11) 0.0081(11) 0.0071(13) O43 0.0543(13) 0.0622(15) 0.0379(12) 0.0081(11) 0.014(1) 0.0098(13) C44 0.058(2) 0.049(2) 0.056(2) -0.0084(16) 0.0105(16) 0.0078(18) C45 0.078(3) 0.049(2) 0.060(2) -0.0065(17) -0.006(2) -0.013(2) C46 0.0420(17) 0.0387(17) 0.0426(16) 0.0058(13) 0.0028(14) 0.0031(15) C47 0.0459(18) 0.0375(17) 0.0489(18) -0.0058(14) 0.0050(15) -0.0013(15) C48 0.048(2) 0.053(2) 0.070(2) -0.0039(18) -0.0053(18) -0.0029(17) C49 0.049(2) 0.067(3) 0.098(3) -0.024(2) -0.011(2) 0.004(2) C50 0.052(2) 0.078(3) 0.114(4) -0.035(3) 0.021(3) -0.018(2) C51 0.080(3) 0.071(3) 0.087(3) -0.010(2) 0.025(3) -0.032(3) C52 0.072(3) 0.052(2) 0.065(2) 0.0004(19) 0.008(2) -0.014(2) C53 0.0474(18) 0.0520(19) 0.0362(16) 0.0129(14) -0.0024(14) -0.0005(16) C54 0.0458(17) 0.0494(18) 0.0422(17) 0.0115(14) -0.0069(15) -0.0006(17) O55 0.0489(13) 0.0458(12) 0.035(1) 0.0056(9) -0.007(1) -0.0026(11) C56 0.0376(16) 0.0467(18) 0.0350(16) 0.0007(14) -0.0019(13) 0.0045(15) N57 0.0490(15) 0.0471(15) 0.0313(12) -0.0007(11) -0.0007(11) -0.0067(14) O58 0.0592(14) 0.0562(14) 0.0371(11) 0.012(1) 0.0007(11) -0.0098(12) C59 0.078(3) 0.084(3) 0.0335(17) 0.0078(17) -0.0134(17) -0.009(2) C60 0.0456(19) 0.065(2) 0.067(2) 0.0119(19) -0.0131(17) 0.001(2) _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 . 1.510(4) yes C1 . C8 . 1.523(4) yes C1 . H11 . 1.021 no C1 . N12 . 1.450(4) yes C2 . C3 . 1.399(5) yes C2 . C7 . 1.385(5) yes C3 . C4 . 1.369(6) yes C3 . H31 . 1.052 no C4 . C5 . 1.363(8) yes C4 . H41 . 1.047 no C5 . C6 . 1.395(8) yes C5 . H51 . 0.989 no C6 . C7 . 1.422(6) yes C6 . H61 . 1.007 no C7 . H71 . 1.044 no C8 . C9 . 1.509(4) yes C8 . H81 . 1.009 no C8 . H82 . 1.008 no C9 . O10 . 1.477(4) yes C9 . C14 . 1.517(5) yes C9 . C15 . 1.514(5) yes O10 . C11 . 1.343(4) yes C11 . N12 . 1.328(4) yes C11 . O13 . 1.234(3) yes N12 . H121 . 0.969 no C14 . H141 . 1.004 no C14 . H142 . 1.005 no C14 . H143 . 1.023 no C15 . H151 . 1.003 no C15 . H152 . 1.006 no C15 . H153 . 1.020 no C16 . C17 . 1.512(4) yes C16 . C23 . 1.524(4) yes C16 . N27 . 1.458(4) yes C16 . H161 . 1.015 no C17 . C18 . 1.387(4) yes C17 . C22 . 1.388(5) yes C18 . C19 . 1.391(5) yes C18 . H181 . 1.009 no C19 . C20 . 1.382(5) yes C19 . H191 . 1.015 no C20 . C21 . 1.365(6) yes C20 . H201 . 1.005 no C21 . C22 . 1.390(5) yes C21 . H211 . 1.027 no C22 . H221 . 1.033 no C23 . C24 . 1.513(5) yes C23 . H231 . 1.017 no C23 . H232 . 1.006 no C24 . O25 . 1.477(4) yes C24 . C29 . 1.511(5) yes C24 . C30 . 1.518(5) yes O25 . C26 . 1.344(4) yes C26 . N27 . 1.346(4) yes C26 . O28 . 1.226(4) yes N27 . H271 . 1.006 no C29 . H291 . 0.987 no C29 . H292 . 1.017 no C29 . H293 . 1.022 no C30 . H301 . 1.012 no C30 . H302 . 1.028 no C30 . H303 . 1.001 no C31 . C32 . 1.515(4) yes C31 . C38 . 1.519(4) yes C31 . N42 . 1.462(4) yes C31 . H311 . 1.013 no C32 . C33 . 1.397(4) yes C32 . C37 . 1.381(4) yes C33 . C34 . 1.378(5) yes C33 . H331 . 1.020 no C34 . C35 . 1.367(5) yes C34 . H341 . 1.027 no C35 . C36 . 1.378(5) yes C35 . H351 . 1.017 no C36 . C37 . 1.390(5) yes C36 . H361 . 1.016 no C37 . H371 . 1.010 no C38 . C39 . 1.513(4) yes C38 . H381 . 1.012 no C38 . H382 . 1.019 no C39 . O40 . 1.468(3) yes C39 . C44 . 1.514(5) yes C39 . C45 . 1.513(5) yes O40 . C41 . 1.346(4) yes C41 . N42 . 1.334(4) yes C41 . O43 . 1.224(3) yes N42 . H421 . 1.048 no C44 . H441 . 1.012 no C44 . H442 . 0.990 no C44 . H443 . 1.015 no C45 . H451 . 1.002 no C45 . H452 . 0.996 no C45 . H453 . 1.034 no C46 . C47 . 1.511(4) yes C46 . C53 . 1.517(4) yes C46 . N57 . 1.458(4) yes C46 . H461 . 1.006 no C47 . C48 . 1.377(5) yes C47 . C52 . 1.397(5) yes C48 . C49 . 1.401(5) yes C48 . H481 . 1.044 no C49 . C50 . 1.372(6) yes C49 . H491 . 1.033 no C50 . C51 . 1.365(7) yes C50 . H501 . 1.015 no C51 . C52 . 1.391(6) yes C51 . H511 . 1.030 no C52 . H521 . 1.040 no C53 . C54 . 1.512(5) yes C53 . H531 . 0.995 no C53 . H532 . 1.016 no C54 . O55 . 1.472(4) yes C54 . C59 . 1.519(5) yes C54 . C60 . 1.525(5) yes O55 . C56 . 1.357(3) yes C56 . N57 . 1.328(4) yes C56 . O58 . 1.225(3) yes N57 . H571 . 0.940 no C59 . H591 . 1.022 no C59 . H592 . 0.993 no C59 . H593 . 1.017 no C60 . H601 . 0.998 no C60 . H602 . 1.022 no C60 . H603 . 0.996 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 . C8 . 112.2(2) yes C2 . C1 . H11 . 107.666 no C8 . C1 . H11 . 107.995 no C2 . C1 . N12 . 109.8(2) yes C8 . C1 . N12 . 108.1(3) yes H11 . C1 . N12 . 111.081 no C1 . C2 . C3 . 120.4(3) yes C1 . C2 . C7 . 120.6(3) yes C3 . C2 . C7 . 119.1(4) yes C2 . C3 . C4 . 121.6(5) yes C2 . C3 . H31 . 118.586 no C4 . C3 . H31 . 119.816 no C3 . C4 . C5 . 120.1(5) yes C3 . C4 . H41 . 119.866 no C5 . C4 . H41 . 120.068 no C4 . C5 . C6 . 120.6(5) yes C4 . C5 . H51 . 120.187 no C6 . C5 . H51 . 119.122 no C5 . C6 . C7 . 119.5(5) yes C5 . C6 . H61 . 118.711 no C7 . C6 . H61 . 121.799 no C2 . C7 . C6 . 119.2(5) yes C2 . C7 . H71 . 120.903 no C6 . C7 . H71 . 119.842 no C1 . C8 . C9 . 111.5(3) yes C1 . C8 . H81 . 108.906 no C9 . C8 . H81 . 110.114 no C1 . C8 . H82 . 107.492 no C9 . C8 . H82 . 110.597 no H81 . C8 . H82 . 108.122 no C8 . C9 . O10 . 109.0(2) yes C8 . C9 . C14 . 112.4(3) yes O10 . C9 . C14 . 108.0(3) yes C8 . C9 . C15 . 112.2(3) yes O10 . C9 . C15 . 104.1(3) yes C14 . C9 . C15 . 110.7(3) yes C9 . O10 . C11 . 121.0(2) yes O10 . C11 . N12 . 119.8(3) yes O10 . C11 . O13 . 117.0(3) yes N12 . C11 . O13 . 123.1(3) yes C1 . N12 . C11 . 126.3(3) yes C1 . N12 . H121 . 107.876 no C11 . N12 . H121 . 125.569 no C9 . C14 . H141 . 111.619 no C9 . C14 . H142 . 111.133 no H141 . C14 . H142 . 108.814 no C9 . C14 . H143 . 110.398 no H141 . C14 . H143 . 107.383 no H142 . C14 . H143 . 107.323 no C9 . C15 . H151 . 111.476 no C9 . C15 . H152 . 110.878 no H151 . C15 . H152 . 108.793 no C9 . C15 . H153 . 110.464 no H151 . C15 . H153 . 107.649 no H152 . C15 . H153 . 107.436 no C17 . C16 . C23 . 111.2(3) yes C17 . C16 . N27 . 112.0(2) yes C23 . C16 . N27 . 107.7(3) yes C17 . C16 . H161 . 107.438 no C23 . C16 . H161 . 109.509 no N27 . C16 . H161 . 109.030 no C16 . C17 . C18 . 122.2(3) yes C16 . C17 . C22 . 119.2(3) yes C18 . C17 . C22 . 118.5(3) yes C17 . C18 . C19 . 120.2(3) yes C17 . C18 . H181 . 119.871 no C19 . C18 . H181 . 119.971 no C18 . C19 . C20 . 120.7(3) yes C18 . C19 . H191 . 119.964 no C20 . C19 . H191 . 119.292 no C19 . C20 . C21 . 119.3(3) yes C19 . C20 . H201 . 119.459 no C21 . C20 . H201 . 121.125 no C20 . C21 . C22 . 120.5(3) yes C20 . C21 . H211 . 120.454 no C22 . C21 . H211 . 118.873 no C17 . C22 . C21 . 120.7(3) yes C17 . C22 . H221 . 119.630 no C21 . C22 . H221 . 119.619 no C16 . C23 . C24 . 111.5(3) yes C16 . C23 . H231 . 107.995 no C24 . C23 . H231 . 109.679 no C16 . C23 . H232 . 109.447 no C24 . C23 . H232 . 110.463 no H231 . C23 . H232 . 107.598 no C23 . C24 . O25 . 108.7(2) yes C23 . C24 . C29 . 111.7(3) yes O25 . C24 . C29 . 104.7(3) yes C23 . C24 . C30 . 113.6(3) yes O25 . C24 . C30 . 107.1(3) yes C29 . C24 . C30 . 110.5(3) yes C24 . O25 . C26 . 121.5(3) yes O25 . C26 . N27 . 119.6(3) yes O25 . C26 . O28 . 117.4(3) yes N27 . C26 . O28 . 122.9(3) yes C16 . N27 . C26 . 125.6(3) yes C16 . N27 . H271 . 124.637 no C26 . N27 . H271 . 109.100 no C24 . C29 . H291 . 111.991 no C24 . C29 . H292 . 110.241 no H291 . C29 . H292 . 109.136 no C24 . C29 . H293 . 110.123 no H291 . C29 . H293 . 108.759 no H292 . C29 . H293 . 106.421 no C24 . C30 . H301 . 111.583 no C24 . C30 . H302 . 110.427 no H301 . C30 . H302 . 106.334 no C24 . C30 . H303 . 112.592 no H301 . C30 . H303 . 108.424 no H302 . C30 . H303 . 107.189 no C32 . C31 . C38 . 109.6(2) yes C32 . C31 . N42 . 112.8(2) yes C38 . C31 . N42 . 107.2(2) yes C32 . C31 . H311 . 108.119 no C38 . C31 . H311 . 111.392 no N42 . C31 . H311 . 107.767 no C31 . C32 . C33 . 117.1(3) yes C31 . C32 . C37 . 124.0(3) yes C33 . C32 . C37 . 118.8(3) yes C32 . C33 . C34 . 120.5(3) yes C32 . C33 . H331 . 119.342 no C34 . C33 . H331 . 120.128 no C33 . C34 . C35 . 120.6(3) yes C33 . C34 . H341 . 119.070 no C35 . C34 . H341 . 120.230 no C34 . C35 . C36 . 119.4(3) yes C34 . C35 . H351 . 119.080 no C36 . C35 . H351 . 121.494 no C35 . C36 . C37 . 120.8(3) yes C35 . C36 . H361 . 120.503 no C37 . C36 . H361 . 118.642 no C32 . C37 . C36 . 119.8(3) yes C32 . C37 . H371 . 120.931 no C36 . C37 . H371 . 119.212 no C31 . C38 . C39 . 112.2(3) yes C31 . C38 . H381 . 109.184 no C39 . C38 . H381 . 109.983 no C31 . C38 . H382 . 108.100 no C39 . C38 . H382 . 110.144 no H381 . C38 . H382 . 107.070 no C38 . C39 . O40 . 108.9(2) yes C38 . C39 . C44 . 110.8(3) yes O40 . C39 . C44 . 104.8(2) yes C38 . C39 . C45 . 112.7(3) yes O40 . C39 . C45 . 106.8(3) yes C44 . C39 . C45 . 112.3(3) yes C39 . O40 . C41 . 123.0(2) yes O40 . C41 . N42 . 119.8(3) yes O40 . C41 . O43 . 116.8(3) yes N42 . C41 . O43 . 123.4(3) yes C31 . N42 . C41 . 125.0(3) yes C31 . N42 . H421 . 108.145 no C41 . N42 . H421 . 124.803 no C39 . C44 . H441 . 110.155 no C39 . C44 . H442 . 110.892 no H441 . C44 . H442 . 109.277 no C39 . C44 . H443 . 110.002 no H441 . C44 . H443 . 107.356 no H442 . C44 . H443 . 109.081 no C39 . C45 . H451 . 111.951 no C39 . C45 . H452 . 111.658 no H451 . C45 . H452 . 109.578 no C39 . C45 . H453 . 109.685 no H451 . C45 . H453 . 106.641 no H452 . C45 . H453 . 107.090 no C47 . C46 . C53 . 111.3(2) yes C47 . C46 . N57 . 111.7(3) yes C53 . C46 . N57 . 108.9(3) yes C47 . C46 . H461 . 109.066 no C53 . C46 . H461 . 107.588 no N57 . C46 . H461 . 108.271 no C46 . C47 . C48 . 123.6(3) yes C46 . C47 . C52 . 118.2(3) yes C48 . C47 . C52 . 118.3(3) yes C47 . C48 . C49 . 121.1(4) yes C47 . C48 . H481 . 120.161 no C49 . C48 . H481 . 118.772 no C48 . C49 . C50 . 119.8(4) yes C48 . C49 . H491 . 119.719 no C50 . C49 . H491 . 120.461 no C49 . C50 . C51 . 119.7(4) yes C49 . C50 . H501 . 120.733 no C51 . C50 . H501 . 119.508 no C50 . C51 . C52 . 120.9(4) yes C50 . C51 . H511 . 119.706 no C52 . C51 . H511 . 119.320 no C47 . C52 . C51 . 120.1(4) yes C47 . C52 . H521 . 120.013 no C51 . C52 . H521 . 119.821 no C46 . C53 . C54 . 112.3(3) yes C46 . C53 . H531 . 109.778 no C54 . C53 . H531 . 109.838 no C46 . C53 . H532 . 108.183 no C54 . C53 . H532 . 108.102 no H531 . C53 . H532 . 108.574 no C53 . C54 . O55 . 106.9(2) yes C53 . C54 . C59 . 112.1(3) yes O55 . C54 . C59 . 104.4(3) yes C53 . C54 . C60 . 113.7(3) yes O55 . C54 . C60 . 107.7(3) yes C59 . C54 . C60 . 111.3(3) yes C54 . O55 . C56 . 117.4(2) yes O55 . C56 . N57 . 118.7(3) yes O55 . C56 . O58 . 117.4(3) yes N57 . C56 . O58 . 123.9(3) yes C46 . N57 . C56 . 127.9(2) yes C46 . N57 . H571 . 113.462 no C56 . N57 . H571 . 118.587 no C54 . C59 . H591 . 110.441 no C54 . C59 . H592 . 112.424 no H591 . C59 . H592 . 108.251 no C54 . C59 . H593 . 110.370 no H591 . C59 . H593 . 106.426 no H592 . C59 . H593 . 108.720 no C54 . C60 . H601 . 110.774 no C54 . C60 . H602 . 109.475 no H601 . C60 . H602 . 107.875 no C54 . C60 . H603 . 110.566 no H601 . C60 . H603 . 109.981 no H602 . C60 . H603 . 108.088 no # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # Attachment 'CCDC280053.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 280053' _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 '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 17.9151(5) _cell_angle_alpha 90 _cell_length_b 9.5994(3) _cell_angle_beta 119.6642(13) _cell_length_c 12.1722(4) _cell_angle_gamma 90 _cell_volume 1819.0(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 'C19 H27 N1 O4' _chemical_formula_moiety 'C19 H27 N1 O4' _chemical_compound_source ? _chemical_formula_weight 333.43 _cell_measurement_reflns_used 2024 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 190 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 720.000 _exptl_absorpt_coefficient_mu 0.085 # 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 3934 _reflns_number_total 2192 _diffrn_reflns_av_R_equivalents 0.01 # Number of reflections with Friedels Law is 2192 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2083 _diffrn_reflns_theta_min 5.107 _diffrn_reflns_theta_max 27.472 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.511 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -22 _reflns_limit_h_max 20 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _refine_diff_density_min -0.13 _refine_diff_density_max 0.17 _refine_ls_number_reflns 1765 _refine_ls_number_parameters 217 #_refine_ls_R_factor_ref 0.0324 _refine_ls_wR_factor_ref 0.0365 _refine_ls_goodness_of_fit_ref 1.1371 #_reflns_number_all 2192 _refine_ls_R_factor_all 0.0424 _refine_ls_wR_factor_all 0.0465 # 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 1765 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_gt 0.0365 _refine_ls_shift/su_max 0.000389 _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 0.599 0.224 0.274 0.558E-01 ; _diffrn_radiation_probe ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 COLLECT Software, Nonius BV 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_attached_hydrogens # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom N1 N 0.9100(1) 0.22712(19) 0.20239(15) 0.0283 1.0000 Uani . C2 C 0.82720(11) 0.3044(2) 0.16086(18) 0.0288 1.0000 Uani . C3 C 0.82475(12) 0.4349(2) 0.08828(18) 0.0306 1.0000 Uani . C4 C 0.87441(11) 0.4168(2) 0.01792(18) 0.0297 1.0000 Uani . O5 O 0.96408(8) 0.38944(16) 0.11710(13) 0.0321 1.0000 Uani . C6 C 0.98168(11) 0.2948(2) 0.20682(18) 0.0286 1.0000 Uani . O7 O 1.05499(8) 0.26962(18) 0.28312(15) 0.0395 1.0000 Uani . C8 C 0.84283(13) 0.2990(3) -0.07766(19) 0.0388 1.0000 Uani . C9 C 0.87977(14) 0.5523(3) -0.0417(2) 0.0387 1.0000 Uani . C10 C 0.81482(14) 0.3339(3) 0.2754(2) 0.0385 1.0000 Uani . C11 C 0.72781(14) 0.4025(3) 0.2320(2) 0.0414 1.0000 Uani . C12 C 0.88683(16) 0.4231(5) 0.3766(2) 0.0701 1.0000 Uani . C13 C 0.91114(12) 0.0868(2) 0.23032(19) 0.0291 1.0000 Uani . C14 C 0.98907(11) -0.0027(2) 0.26157(18) 0.0278 1.0000 Uani . C15 C 0.98444(12) -0.1396(2) 0.32426(19) 0.0310 1.0000 Uani . C16 C 1.06871(12) -0.2178(2) 0.37967(18) 0.0291 1.0000 Uani . C17 C 1.07852(14) -0.3353(2) 0.3224(2) 0.0381 1.0000 Uani . C18 C 1.15727(16) -0.4022(3) 0.3729(2) 0.0444 1.0000 Uani . C19 C 1.22735(14) -0.3522(3) 0.4821(2) 0.0431 1.0000 Uani . C20 C 1.21798(13) -0.2352(3) 0.5414(2) 0.0384 1.0000 Uani . C21 C 1.13892(13) -0.1684(2) 0.4905(2) 0.0333 1.0000 Uani . H21 H 0.7778 0.2445 0.0999 0.0371 1.0000 Uiso . O22 O 0.91670(9) -0.22767(19) 0.23644(17) 0.0466 1.0000 Uani . C23 C 0.99367(16) -0.0283(3) 0.1402(2) 0.0425 1.0000 Uani . O24 O 0.84584(9) 0.03440(17) 0.22145(16) 0.0400 1.0000 Uani . H31 H 0.8502 0.5140 0.1505 0.0408 1.0000 Uiso . H32 H 0.7633 0.4579 0.0266 0.0408 1.0000 Uiso . H81 H 0.8781 0.2936 -0.1206 0.0496 1.0000 Uiso . H82 H 0.8462 0.2086 -0.0351 0.0496 1.0000 Uiso . H83 H 0.7810 0.3167 -0.1440 0.0496 1.0000 Uiso . H91 H 0.9126 0.5381 -0.0882 0.0497 1.0000 Uiso . H92 H 0.9090 0.6259 0.0240 0.0497 1.0000 Uiso . H93 H 0.8201 0.5855 -0.1045 0.0497 1.0000 Uiso . H101 H 0.8169 0.2394 0.3170 0.0517 1.0000 Uiso . H111 H 0.7185 0.4229 0.3046 0.0558 1.0000 Uiso . H112 H 0.7261 0.4948 0.1890 0.0558 1.0000 Uiso . H113 H 0.6797 0.3433 0.1687 0.0558 1.0000 Uiso . H121 H 0.8770 0.4381 0.4496 0.0820 1.0000 Uiso . H122 H 0.9439 0.3753 0.4076 0.0820 1.0000 Uiso . H123 H 0.8880 0.5147 0.3386 0.0820 1.0000 Uiso . H141 H 1.0437 0.0479 0.3234 0.0366 1.0000 Uiso . H151 H 0.9724 -0.1160 0.3951 0.0395 1.0000 Uiso . H171 H 1.0271 -0.3728 0.2436 0.0442 1.0000 Uiso . H181 H 1.1639 -0.4882 0.3298 0.0551 1.0000 Uiso . H191 H 1.2852 -0.3987 0.5187 0.0493 1.0000 Uiso . H201 H 1.2679 -0.1987 0.6207 0.0469 1.0000 Uiso . H211 H 1.1325 -0.0846 0.5346 0.0400 1.0000 Uiso . H221 H 0.8667 -0.1700 0.2212 0.0500 1.0000 Uiso . H231 H 1.0446 -0.0875 0.1583 0.0593 1.0000 Uiso . H232 H 0.9970 0.0614 0.1011 0.0593 1.0000 Uiso . H233 H 0.9399 -0.0797 0.0764 0.0593 1.0000 Uiso . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0196(7) 0.0334(9) 0.0310(8) 0.0039(7) 0.0118(6) 0.0038(7) C2 0.0196(8) 0.0352(11) 0.0307(9) 0.0022(9) 0.0117(7) 0.0043(8) C3 0.0257(9) 0.0357(11) 0.0304(9) 0.0029(9) 0.0139(7) 0.0050(9) C4 0.0192(8) 0.0389(12) 0.0284(9) 0.0042(9) 0.0096(7) 0.0037(8) O5 0.0197(6) 0.0381(8) 0.0345(7) 0.0064(7) 0.0104(5) 0.0006(6) C6 0.0209(8) 0.0304(11) 0.0315(9) -0.0015(9) 0.0106(7) -0.0014(8) O7 0.0190(6) 0.0405(9) 0.0463(8) 0.0081(7) 0.0066(6) -0.0012(6) C8 0.031(1) 0.0528(15) 0.032(1) -0.0050(11) 0.0155(8) -0.000(1) C9 0.028(1) 0.0462(12) 0.0412(11) 0.0125(11) 0.0170(9) 0.005(1) C10 0.0347(11) 0.0521(14) 0.033(1) 0.007(1) 0.0204(9) 0.012(1) C11 0.0349(11) 0.0518(15) 0.0445(11) 0.0001(11) 0.0250(9) 0.0075(11) C12 0.0398(13) 0.130(3) 0.0351(12) -0.0217(18) 0.015(1) 0.0052(18) C13 0.0224(9) 0.0353(11) 0.029(1) 0.0014(8) 0.0125(8) 0.0017(8) C14 0.0220(9) 0.033(1) 0.0298(9) 0.0010(9) 0.0136(7) 0.0004(8) C15 0.0245(9) 0.0350(11) 0.035(1) 0.0012(9) 0.0154(8) -0.0020(8) C16 0.0288(9) 0.030(1) 0.0301(9) 0.0063(9) 0.0159(7) -0.0007(9) C17 0.0383(11) 0.0334(11) 0.0348(11) 0.001(1) 0.0121(9) 0.002(1) C18 0.0487(13) 0.0352(12) 0.0473(12) 0.0023(11) 0.022(1) 0.0103(11) C19 0.0380(11) 0.0420(13) 0.0459(13) 0.0126(11) 0.018(1) 0.0111(11) C20 0.030(1) 0.0406(12) 0.037(1) 0.007(1) 0.0113(8) -0.001(1) C21 0.031(1) 0.0347(11) 0.034(1) 0.0022(9) 0.0159(8) -0.0009(9) O22 0.0264(7) 0.0398(9) 0.062(1) -0.0030(8) 0.0127(7) -0.0043(7) C23 0.0467(13) 0.0499(14) 0.0390(12) 0.011(1) 0.027(1) 0.0146(11) O24 0.0248(7) 0.0385(9) 0.059(1) 0.0072(8) 0.0221(7) 0.0004(6) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C2 . 1.505(2) yes N1 . C6 . 1.415(2) yes N1 . C13 . 1.387(3) yes C2 . C3 . 1.521(3) yes C2 . C10 . 1.542(3) yes C2 . H21 . 1.007 no C3 . C4 . 1.520(3) yes C3 . H31 . 1.008 no C3 . H32 . 1.004 no C4 . O5 . 1.479(2) yes C4 . C8 . 1.516(3) yes C4 . C9 . 1.516(3) yes O5 . C6 . 1.333(2) yes C6 . O7 . 1.199(2) yes C8 . H81 . 1.001 no C8 . H82 . 0.997 no C8 . H83 . 1.012 no C9 . H91 . 1.006 no C9 . H92 . 0.999 no C9 . H93 . 1.011 no C10 . C11 . 1.525(3) yes C10 . C12 . 1.531(4) yes C10 . H101 . 1.030 no C11 . H111 . 0.997 no C11 . H112 . 1.023 no C11 . H113 . 1.001 no C12 . H121 . 0.998 no C12 . H122 . 1.008 no C12 . H123 . 0.998 no C13 . C14 . 1.518(3) yes C13 . O24 . 1.228(2) yes C14 . C15 . 1.543(3) yes C14 . C23 . 1.540(3) yes C14 . H141 . 1.015 no C15 . C16 . 1.513(3) yes C15 . O22 . 1.430(3) yes C15 . H151 . 1.012 no C16 . C17 . 1.382(3) yes C16 . C21 . 1.395(3) yes C17 . C18 . 1.387(3) yes C17 . H171 . 1.012 no C18 . C19 . 1.387(4) yes C18 . H181 . 1.015 no C19 . C20 . 1.388(4) yes C19 . H191 . 1.008 no C20 . C21 . 1.390(3) yes C20 . H201 . 1.000 no C21 . H211 . 1.004 no O22 . H221 . 0.990 no C23 . H231 . 1.003 no C23 . H232 . 1.000 no C23 . H233 . 1.017 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C6 . 120.77(16) yes C2 . N1 . C13 . 116.92(16) yes C6 . N1 . C13 . 122.25(16) yes N1 . C2 . C3 . 109.93(15) yes N1 . C2 . C10 . 110.24(15) yes C3 . C2 . C10 . 113.45(18) yes N1 . C2 . H21 . 109.159 no C3 . C2 . H21 . 106.259 no C10 . C2 . H21 . 107.625 no C2 . C3 . C4 . 112.12(17) yes C2 . C3 . H31 . 108.171 no C4 . C3 . H31 . 109.638 no C2 . C3 . H32 . 108.753 no C4 . C3 . H32 . 109.585 no H31 . C3 . H32 . 108.495 no C3 . C4 . O5 . 105.23(14) yes C3 . C4 . C8 . 114.67(17) yes O5 . C4 . C8 . 109.64(17) yes C3 . C4 . C9 . 111.43(18) yes O5 . C4 . C9 . 104.03(16) yes C8 . C4 . C9 . 111.11(17) yes C4 . O5 . C6 . 120.70(15) yes N1 . C6 . O5 . 116.05(15) yes N1 . C6 . O7 . 124.19(19) yes O5 . C6 . O7 . 119.73(17) yes C4 . C8 . H81 . 110.300 no C4 . C8 . H82 . 110.304 no H81 . C8 . H82 . 109.570 no C4 . C8 . H83 . 109.435 no H81 . C8 . H83 . 108.435 no H82 . C8 . H83 . 108.756 no C4 . C9 . H91 . 110.287 no C4 . C9 . H92 . 110.833 no H91 . C9 . H92 . 109.018 no C4 . C9 . H93 . 109.833 no H91 . C9 . H93 . 108.119 no H92 . C9 . H93 . 108.689 no C2 . C10 . C11 . 110.22(16) yes C2 . C10 . C12 . 112.92(19) yes C11 . C10 . C12 . 110.3(2) yes C2 . C10 . H101 . 107.216 no C11 . C10 . H101 . 109.394 no C12 . C10 . H101 . 106.637 no C10 . C11 . H111 . 111.599 no C10 . C11 . H112 . 108.522 no H111 . C11 . H112 . 107.940 no C10 . C11 . H113 . 111.375 no H111 . C11 . H113 . 109.656 no H112 . C11 . H113 . 107.598 no C10 . C12 . H121 . 110.358 no C10 . C12 . H122 . 109.927 no H121 . C12 . H122 . 108.983 no C10 . C12 . H123 . 108.793 no H121 . C12 . H123 . 109.811 no H122 . C12 . H123 . 108.949 no N1 . C13 . C14 . 120.68(17) yes N1 . C13 . O24 . 118.60(18) yes C14 . C13 . O24 . 120.56(19) yes C13 . C14 . C15 . 109.74(16) yes C13 . C14 . C23 . 109.23(16) yes C15 . C14 . C23 . 112.33(18) yes C13 . C14 . H141 . 110.219 no C15 . C14 . H141 . 107.987 no C23 . C14 . H141 . 107.300 no C14 . C15 . C16 . 110.91(16) yes C14 . C15 . O22 . 111.56(16) yes C16 . C15 . O22 . 109.30(18) yes C14 . C15 . H151 . 108.439 no C16 . C15 . H151 . 108.490 no O22 . C15 . H151 . 108.044 no C15 . C16 . C17 . 121.85(18) yes C15 . C16 . C21 . 119.06(19) yes C17 . C16 . C21 . 119.08(19) yes C16 . C17 . C18 . 120.7(2) yes C16 . C17 . H171 . 119.027 no C18 . C17 . H171 . 120.298 no C17 . C18 . C19 . 120.3(2) yes C17 . C18 . H181 . 120.051 no C19 . C18 . H181 . 119.672 no C18 . C19 . C20 . 119.6(2) yes C18 . C19 . H191 . 121.016 no C20 . C19 . H191 . 119.420 no C19 . C20 . C21 . 120.0(2) yes C19 . C20 . H201 . 120.289 no C21 . C20 . H201 . 119.692 no C16 . C21 . C20 . 120.4(2) yes C16 . C21 . H211 . 120.127 no C20 . C21 . H211 . 119.486 no C15 . O22 . H221 . 99.437 no C14 . C23 . H231 . 110.796 no C14 . C23 . H232 . 111.293 no H231 . C23 . H232 . 109.258 no C14 . C23 . H233 . 109.303 no H231 . C23 . H233 . 107.938 no H232 . C23 . H233 . 108.156 no # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # Attachment 'CCDC280054.cif' data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 280054' _audit_creation_date 04-18-08 _audit_creation_method CRYSTALS_ver_12-03-99 _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 8.8735(2) _cell_angle_alpha 89.749(2) _cell_length_b 9.7635(3) _cell_angle_beta 79.982(2) _cell_length_c 11.2480(3) _cell_angle_gamma 64.9723(11) _cell_volume 866.90(4) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_int_tables_number 1 loop_ _symmetry_equiv_pos_as_xyz x,y,z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum 'C16 H29 N1 O4' _chemical_formula_moiety 'C16 H29 N1 O4' _chemical_compound_source ? _chemical_formula_weight 299.41 _cell_measurement_reflns_used 3610 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 190 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 1.147 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 328.000 _exptl_absorpt_coefficient_mu 0.081 # Sheldrick geometric definitions 1.00 1.00 _diffrn_measurement_device_type ; Enraf Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; USER DEFINED STRUCTURE SOLUTION ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 1.00 _exptl_absorpt_correction_T_max 1.00 _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 7230 _reflns_number_total 3878 _diffrn_reflns_av_R_equivalents 0.01 # Number of reflections with Friedels Law is 3878 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3943 _diffrn_reflns_theta_min 5.109 _diffrn_reflns_theta_max 27.408 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 24.873 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _refine_diff_density_min -0.17 _refine_diff_density_max 0.16 _refine_ls_number_reflns 3145 _refine_ls_number_parameters 379 #_refine_ls_R_factor_ref 0.0369 _refine_ls_wR_factor_ref 0.0380 _refine_ls_goodness_of_fit_ref 1.1334 #_reflns_number_all 3878 _refine_ls_R_factor_all 0.0497 _refine_ls_wR_factor_all 0.0482 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 3145 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_gt 0.0380 _refine_ls_shift/su_max 0.000145 _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 0.647 0.842E-01 0.320 ; _diffrn_radiation_probe ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; User-defined structure solution reference COLLECT Software, Nonius BV 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_attached_hydrogens N1 N -0.4664(2) -0.16285(19) -0.13616(16) 0.0295 1.0000 Uani . C2 C -0.5454(3) -0.0222(2) -0.05057(19) 0.0311 1.0000 Uani . C3 C -0.7325(3) 0.0660(2) -0.0548(2) 0.0349 1.0000 Uani . C4 C -0.8096(3) -0.0371(3) -0.0852(2) 0.0344 1.0000 Uani . O5 O -0.7145(2) -0.11136(18) -0.20663(15) 0.0365 1.0000 Uani . C6 C -0.5457(3) -0.1768(2) -0.22916(19) 0.0312 1.0000 Uani . O7 O -0.4732(2) -0.2427(2) -0.32761(14) 0.0434 1.0000 Uani . C8 C -0.8004(3) -0.1567(3) 0.0040(2) 0.0426 1.0000 Uani . C9 C -0.9907(3) 0.0514(3) -0.1047(3) 0.0481 1.0000 Uani . C10 C -0.4409(3) 0.0707(3) -0.0789(2) 0.0404 1.0000 Uani . C11 C -0.4238(4) 0.1097(4) -0.2098(3) 0.0606 1.0000 Uani . C12 C -0.5175(4) 0.2150(3) 0.0059(3) 0.0563 1.0000 Uani . C13 C -0.3168(3) -0.2785(2) -0.1101(2) 0.0326 1.0000 Uani . C14 C -0.2240(3) -0.4259(2) -0.1900(2) 0.0334 1.0000 Uani . C15 C -0.0334(3) -0.4926(2) -0.18732(19) 0.0303 1.0000 Uani . C16 C 0.0514(3) -0.3892(3) -0.2336(2) 0.0380 1.0000 Uani . C17 C 0.0259(4) -0.3398(3) -0.3606(3) 0.0536 1.0000 Uani . C18 C 0.2390(3) -0.4650(3) -0.2286(3) 0.0523 1.0000 Uani . O19 O 0.0518(2) -0.64025(16) -0.25084(14) 0.0347 1.0000 Uani . C20 C -0.3017(3) -0.5338(3) -0.1411(3) 0.0534 1.0000 Uani . O21 O -0.2708(2) -0.2610(2) -0.01867(16) 0.0479 1.0000 Uani . H21 H -0.5430 -0.0503 0.0361 0.0384 1.0000 Uiso . N22 N -0.1148(2) -0.6490(2) -0.64835(17) 0.0360 1.0000 Uani . C23 C -0.1808(3) -0.4794(3) -0.6453(2) 0.0381 1.0000 Uani . C24 C -0.3394(3) -0.4114(3) -0.7010(3) 0.0467 1.0000 Uani . C25 C -0.4339(3) -0.5091(3) -0.6889(3) 0.0507 1.0000 Uani . O26 O -0.3147(2) -0.6578(2) -0.75320(19) 0.0536 1.0000 Uani . C27 C -0.1586(3) -0.7274(3) -0.7306(2) 0.0428 1.0000 Uani . O28 O -0.0645(3) -0.8512(2) -0.77974(18) 0.0585 1.0000 Uani . C29 C -0.4973(4) -0.5303(4) -0.5593(3) 0.0640 1.0000 Uani . C30 C -0.5773(4) -0.4534(4) -0.7602(4) 0.0754 1.0000 Uani . C31 C -0.0371(3) -0.4371(3) -0.7050(2) 0.0427 1.0000 Uani . H31 H -0.7947 0.1246 0.0247 0.0439 1.0000 Uiso . C32 C 0.0290(4) -0.4955(4) -0.8373(3) 0.0559 1.0000 Uani . H32 H -0.7435 0.1394 -0.1198 0.0439 1.0000 Uiso . C33 C -0.0932(4) -0.2674(3) -0.6896(3) 0.0598 1.0000 Uani . C34 C -0.0227(3) -0.7178(3) -0.5599(2) 0.0360 1.0000 Uani . C35 C 0.0455(3) -0.8875(3) -0.5487(2) 0.0398 1.0000 Uani . C36 C 0.2133(3) -0.9455(3) -0.5038(2) 0.0385 1.0000 Uani . C37 C 0.3468(4) -0.9071(3) -0.5839(3) 0.0555 1.0000 Uani . C38 C 0.5047(5) -0.9543(5) -0.5292(4) 0.0761 1.0000 Uani . C39 C 0.3884(4) -0.9768(5) -0.7135(3) 0.0775 1.0000 Uani . O40 O 0.2710(3) -1.10624(19) -0.50097(17) 0.0507 1.0000 Uani . C41 C -0.0907(4) -0.9124(4) -0.4585(4) 0.0688 1.0000 Uani . O42 O -0.0062(3) -0.6366(2) -0.48609(16) 0.0515 1.0000 Uani . H81 H -0.8544 -0.2202 -0.0242 0.0564 1.0000 Uiso . H82 H -0.8597 -0.1089 0.0859 0.0564 1.0000 Uiso . H83 H -0.6783 -0.2248 0.0045 0.0564 1.0000 Uiso . H91 H -1.0402 -0.0194 -0.1234 0.0605 1.0000 Uiso . H92 H -1.0644 0.1192 -0.0301 0.0605 1.0000 Uiso . H93 H -0.9921 0.1167 -0.1743 0.0605 1.0000 Uiso . H101 H -0.3229 0.0026 -0.0644 0.0536 1.0000 Uiso . H111 H -0.3557 0.1694 -0.2262 0.0748 1.0000 Uiso . H112 H -0.5405 0.1726 -0.2291 0.0748 1.0000 Uiso . H113 H -0.3687 0.0151 -0.2673 0.0748 1.0000 Uiso . H121 H -0.4488 0.2750 -0.0119 0.0742 1.0000 Uiso . H122 H -0.6366 0.2802 -0.0042 0.0742 1.0000 Uiso . H123 H -0.5202 0.1903 0.0936 0.0742 1.0000 Uiso . H141 H -0.2353 -0.4083 -0.2780 0.0410 1.0000 Uiso . H151 H -0.0237 -0.5045 -0.0996 0.0360 1.0000 Uiso . H161 H -0.0045 -0.2923 -0.1792 0.0483 1.0000 Uiso . H171 H 0.0833 -0.2714 -0.3862 0.0695 1.0000 Uiso . H172 H 0.0747 -0.4301 -0.4202 0.0695 1.0000 Uiso . H173 H -0.0983 -0.2817 -0.3614 0.0695 1.0000 Uiso . H181 H 0.2958 -0.3990 -0.2579 0.0688 1.0000 Uiso . H182 H 0.2954 -0.5641 -0.2798 0.0688 1.0000 Uiso . H183 H 0.2538 -0.4873 -0.1423 0.0688 1.0000 Uiso . H191 H 0.0382 -0.6328 -0.3353 0.0500 1.0000 Uiso . H201 H -0.2442 -0.6331 -0.1917 0.0718 1.0000 Uiso . H202 H -0.4258 -0.4879 -0.1439 0.0718 1.0000 Uiso . H203 H -0.2868 -0.5521 -0.0556 0.0718 1.0000 Uiso . H231 H -0.2183 -0.4342 -0.5573 0.0416 1.0000 Uiso . H241 H -0.3037 -0.4019 -0.7903 0.0541 1.0000 Uiso . H242 H -0.4165 -0.3068 -0.6621 0.0541 1.0000 Uiso . H291 H -0.5564 -0.6002 -0.5571 0.0746 1.0000 Uiso . H292 H -0.5754 -0.4333 -0.5138 0.0746 1.0000 Uiso . H293 H -0.3969 -0.5827 -0.5168 0.0746 1.0000 Uiso . H301 H -0.6411 -0.5162 -0.7521 0.0933 1.0000 Uiso . H302 H -0.5305 -0.4528 -0.8488 0.0933 1.0000 Uiso . H303 H -0.6595 -0.3442 -0.7303 0.0933 1.0000 Uiso . H311 H 0.0618 -0.4903 -0.6629 0.0555 1.0000 Uiso . H321 H 0.1219 -0.4684 -0.8728 0.0665 1.0000 Uiso . H322 H -0.0657 -0.4528 -0.8835 0.0665 1.0000 Uiso . H323 H 0.0736 -0.6106 -0.8444 0.0665 1.0000 Uiso . H331 H 0.0011 -0.2410 -0.7309 0.0771 1.0000 Uiso . H332 H -0.1941 -0.2132 -0.7296 0.0771 1.0000 Uiso . H333 H -0.1238 -0.2310 -0.6028 0.0771 1.0000 Uiso . H351 H 0.0718 -0.9464 -0.6299 0.0521 1.0000 Uiso . H361 H 0.1973 -0.8970 -0.4210 0.0448 1.0000 Uiso . H371 H 0.2956 -0.7919 -0.5902 0.0700 1.0000 Uiso . H381 H 0.5925 -0.9302 -0.5800 0.1035 1.0000 Uiso . H382 H 0.5543 -1.0685 -0.5220 0.1035 1.0000 Uiso . H383 H 0.4758 -0.9040 -0.4453 0.1035 1.0000 Uiso . H391 H 0.4748 -0.9456 -0.7625 0.0851 1.0000 Uiso . H392 H 0.4386 -1.0878 -0.7115 0.0851 1.0000 Uiso . H393 H 0.2852 -0.9384 -0.7485 0.0851 1.0000 Uiso . H401 H 0.3479 -1.1500 -0.4444 0.0500 1.0000 Uiso . H411 H -0.0554 -1.0216 -0.4473 0.0951 1.0000 Uiso . H412 H -0.2007 -0.8710 -0.4904 0.0951 1.0000 Uiso . H413 H -0.1117 -0.8554 -0.3789 0.0951 1.0000 Uiso . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0309(9) 0.0238(8) 0.0307(9) -0.0000(7) -0.0064(7) -0.0086(7) C2 0.0326(11) 0.025(1) 0.0321(11) -0.0016(8) -0.0045(9) -0.0096(9) C3 0.0335(11) 0.025(1) 0.0428(13) 0.0043(9) -0.005(1) -0.0096(9) C4 0.0298(11) 0.0320(11) 0.0380(12) 0.0019(9) -0.0062(9) -0.0101(9) O5 0.0351(8) 0.0360(9) 0.0376(8) 0.0020(7) -0.0112(7) -0.0128(7) C6 0.0378(12) 0.027(1) 0.0302(11) 0.0047(9) -0.0104(9) -0.0134(9) O7 0.046(1) 0.045(1) 0.0318(9) -0.0006(7) -0.0119(7) -0.0109(8) C8 0.0444(14) 0.0379(13) 0.0461(14) 0.005(1) -0.0027(11) -0.0204(11) C9 0.0324(13) 0.0451(14) 0.0631(17) 0.0034(12) -0.0127(12) -0.0118(11) C10 0.0365(12) 0.0344(12) 0.0502(14) -0.004(1) -0.002(1) -0.018(1) C11 0.076(2) 0.0485(16) 0.0550(17) -0.0062(13) 0.0182(15) -0.0355(15) C12 0.072(2) 0.0446(15) 0.0585(17) -0.0103(13) 0.0012(15) -0.0356(15) C13 0.0305(11) 0.0296(11) 0.0324(11) -0.0006(9) -0.0062(9) -0.0078(9) C14 0.0348(12) 0.025(1) 0.0377(12) 0.0010(9) -0.0094(9) -0.0091(9) C15 0.0340(11) 0.022(1) 0.0300(11) -0.0018(8) -0.0083(9) -0.0067(8) C16 0.0357(12) 0.0258(11) 0.0493(13) -0.0028(9) -0.008(1) -0.0102(9) C17 0.0616(17) 0.0454(15) 0.0611(17) 0.0198(13) -0.0145(14) -0.0289(13) C18 0.0401(14) 0.0462(15) 0.0727(19) 0.0008(13) -0.0128(13) -0.0195(12) O19 0.0408(9) 0.0212(7) 0.0354(8) 0.0003(6) -0.0077(7) -0.0067(6) C20 0.0420(15) 0.0357(14) 0.084(2) 0.0039(13) -0.0069(14) -0.0201(12) O21 0.045(1) 0.044(1) 0.0398(9) -0.0081(7) -0.0188(8) -0.0002(8) N22 0.037(1) 0.032(1) 0.033(1) -0.0016(8) -0.0083(8) -0.0085(8) C23 0.0364(12) 0.0330(12) 0.0380(12) 0.0016(9) -0.008(1) -0.008(1) C24 0.0339(13) 0.0424(14) 0.0548(16) 0.0067(12) -0.0111(11) -0.0067(11) C25 0.0330(13) 0.0445(15) 0.0654(18) -0.0057(13) -0.0075(12) -0.0084(11) O26 0.040(1) 0.0497(11) 0.0624(12) -0.0131(9) -0.0199(9) -0.0070(8) C27 0.0417(13) 0.0427(14) 0.0375(12) -0.005(1) -0.0130(11) -0.0097(11) O28 0.0577(12) 0.0481(11) 0.0505(11) -0.0172(9) -0.0212(9) -0.0002(9) C29 0.0445(16) 0.0578(18) 0.078(2) -0.0042(16) 0.0089(15) -0.0186(14) C30 0.0434(17) 0.069(2) 0.108(3) -0.002(2) -0.0305(18) -0.0119(15) C31 0.0352(12) 0.0436(13) 0.0456(13) 0.0100(11) -0.012(1) -0.0119(11) C32 0.0430(15) 0.071(2) 0.0450(15) 0.0062(14) -0.0019(12) -0.0180(14) C33 0.0570(18) 0.0466(16) 0.076(2) 0.0121(15) -0.0130(15) -0.0220(14) C34 0.0371(12) 0.0370(12) 0.0294(11) 0.0005(9) -0.0083(9) -0.011(1) C35 0.0461(14) 0.0333(12) 0.0402(13) 0.003(1) -0.0128(11) -0.015(1) C36 0.0475(14) 0.0316(11) 0.0338(12) 0.0033(9) -0.013(1) -0.012(1) C37 0.0499(16) 0.0545(17) 0.0569(17) 0.0175(14) -0.0130(13) -0.0166(13) C38 0.057(2) 0.082(3) 0.092(3) 0.016(2) -0.0243(19) -0.0291(18) C39 0.0568(19) 0.098(3) 0.0444(16) 0.0197(18) -0.0031(14) -0.0044(18) O40 0.0683(13) 0.0324(9) 0.049(1) 0.0079(8) -0.0281(9) -0.0129(9) C41 0.0562(19) 0.065(2) 0.091(3) 0.0287(18) -0.0158(18) -0.0309(16) O42 0.0741(13) 0.0364(9) 0.041(1) -0.0016(8) -0.0255(9) -0.0155(9) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C2 . 1.505(3) yes N1 . C6 . 1.395(3) yes N1 . C13 . 1.410(3) yes C2 . C3 . 1.523(3) yes C2 . C10 . 1.546(3) yes C2 . H21 . 1.013 no C3 . C4 . 1.505(3) yes C3 . H31 . 0.998 no C3 . H32 . 1.010 no C4 . O5 . 1.481(3) yes C4 . C8 . 1.521(3) yes C4 . C9 . 1.524(3) yes O5 . C6 . 1.333(3) yes C6 . O7 . 1.209(3) yes C8 . H81 . 1.011 no C8 . H82 . 0.986 no C8 . H83 . 1.005 no C9 . H91 . 1.003 no C9 . H92 . 1.008 no C9 . H93 . 1.006 no C10 . C11 . 1.517(4) yes C10 . C12 . 1.528(4) yes C10 . H101 . 1.017 no C11 . H111 . 0.998 no C11 . H112 . 1.018 no C11 . H113 . 1.011 no C12 . H121 . 1.007 no C12 . H122 . 1.003 no C12 . H123 . 1.013 no C13 . C14 . 1.519(3) yes C13 . O21 . 1.208(3) yes C14 . C15 . 1.540(3) yes C14 . C20 . 1.537(4) yes C14 . H141 . 1.019 no C15 . C16 . 1.536(3) yes C15 . O19 . 1.435(2) yes C15 . H151 . 1.008 no C16 . C17 . 1.528(4) yes C16 . C18 . 1.521(4) yes C16 . H161 . 1.009 no C17 . H171 . 1.012 no C17 . H172 . 0.998 no C17 . H173 . 1.006 no C18 . H181 . 0.997 no C18 . H182 . 1.006 no C18 . H183 . 1.013 no O19 . H191 . 0.977 no C20 . H201 . 1.005 no C20 . H202 . 1.005 no C20 . H203 . 0.998 no N22 . C23 . 1.503(3) yes N22 . C27 . 1.406(3) yes N22 . C34 . 1.387(3) yes C23 . C24 . 1.525(3) yes C23 . C31 . 1.546(4) yes C23 . H231 . 1.024 no C24 . C25 . 1.506(4) yes C24 . H241 . 1.015 no C24 . H242 . 1.006 no C25 . O26 . 1.481(3) yes C25 . C29 . 1.514(5) yes C25 . C30 . 1.525(4) yes O26 . C27 . 1.330(3) yes C27 . O28 . 1.205(3) yes C29 . H291 . 1.019 no C29 . H292 . 0.983 no C29 . H293 . 1.023 no C30 . H301 . 0.990 no C30 . H302 . 1.012 no C30 . H303 . 1.021 no C31 . C32 . 1.519(4) yes C31 . C33 . 1.516(4) yes C31 . H311 . 1.010 no C32 . H321 . 0.990 no C32 . H322 . 1.002 no C32 . H323 . 1.019 no C33 . H331 . 1.014 no C33 . H332 . 1.010 no C33 . H333 . 0.991 no C34 . C35 . 1.518(3) yes C34 . O42 . 1.219(3) yes C35 . C36 . 1.529(3) yes C35 . C41 . 1.538(4) yes C35 . H351 . 1.018 no C36 . C37 . 1.535(4) yes C36 . O40 . 1.432(3) yes C36 . H361 . 1.006 no C37 . C38 . 1.519(5) yes C37 . C39 . 1.528(5) yes C37 . H371 . 1.027 no C38 . H381 . 0.994 no C38 . H382 . 1.020 no C38 . H383 . 1.005 no C39 . H391 . 1.017 no C39 . H392 . 0.984 no C39 . H393 . 0.983 no O40 . H401 . 0.977 no C41 . H411 . 0.991 no C41 . H412 . 1.016 no C41 . H413 . 1.002 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C6 . 120.50(17) yes C2 . N1 . C13 . 115.38(17) yes C6 . N1 . C13 . 123.99(17) yes N1 . C2 . C3 . 110.78(17) yes N1 . C2 . C10 . 108.89(17) yes C3 . C2 . C10 . 114.07(18) yes N1 . C2 . H21 . 110.377 no C3 . C2 . H21 . 104.839 no C10 . C2 . H21 . 107.777 no C2 . C3 . C4 . 111.67(18) yes C2 . C3 . H31 . 109.731 no C4 . C3 . H31 . 109.976 no C2 . C3 . H32 . 108.343 no C4 . C3 . H32 . 108.241 no H31 . C3 . H32 . 108.812 no C3 . C4 . O5 . 105.37(18) yes C3 . C4 . C8 . 114.6(2) yes O5 . C4 . C8 . 109.84(18) yes C3 . C4 . C9 . 112.0(2) yes O5 . C4 . C9 . 103.76(19) yes C8 . C4 . C9 . 110.6(2) yes C4 . O5 . C6 . 120.35(16) yes N1 . C6 . O5 . 116.74(18) yes N1 . C6 . O7 . 125.1(2) yes O5 . C6 . O7 . 118.14(19) yes C4 . C8 . H81 . 108.722 no C4 . C8 . H82 . 110.746 no H81 . C8 . H82 . 109.764 no C4 . C8 . H83 . 109.029 no H81 . C8 . H83 . 108.240 no H82 . C8 . H83 . 110.284 no C4 . C9 . H91 . 110.680 no C4 . C9 . H92 . 110.678 no H91 . C9 . H92 . 108.573 no C4 . C9 . H93 . 109.783 no H91 . C9 . H93 . 108.754 no H92 . C9 . H93 . 108.311 no C2 . C10 . C11 . 112.8(2) yes C2 . C10 . C12 . 110.5(2) yes C11 . C10 . C12 . 110.1(2) yes C2 . C10 . H101 . 105.757 no C11 . C10 . H101 . 107.661 no C12 . C10 . H101 . 109.752 no C10 . C11 . H111 . 111.529 no C10 . C11 . H112 . 109.837 no H111 . C11 . H112 . 108.182 no C10 . C11 . H113 . 111.261 no H111 . C11 . H113 . 108.725 no H112 . C11 . H113 . 107.158 no C10 . C12 . H121 . 110.587 no C10 . C12 . H122 . 110.398 no H121 . C12 . H122 . 108.647 no C10 . C12 . H123 . 111.063 no H121 . C12 . H123 . 107.888 no H122 . C12 . H123 . 108.166 no N1 . C13 . C14 . 120.59(19) yes N1 . C13 . O21 . 118.20(19) yes C14 . C13 . O21 . 121.04(19) yes C13 . C14 . C15 . 109.69(18) yes C13 . C14 . C20 . 107.3(2) yes C15 . C14 . C20 . 111.55(19) yes C13 . C14 . H141 . 111.193 no C15 . C14 . H141 . 106.638 no C20 . C14 . H141 . 110.507 no C14 . C15 . C16 . 114.11(17) yes C14 . C15 . O19 . 109.94(16) yes C16 . C15 . O19 . 111.61(18) yes C14 . C15 . H151 . 106.196 no C16 . C15 . H151 . 106.490 no O19 . C15 . H151 . 108.121 no C15 . C16 . C17 . 113.7(2) yes C15 . C16 . C18 . 110.3(2) yes C17 . C16 . C18 . 110.5(2) yes C15 . C16 . H161 . 107.974 no C17 . C16 . H161 . 105.184 no C18 . C16 . H161 . 108.989 no C16 . C17 . H171 . 110.390 no C16 . C17 . H172 . 110.396 no H171 . C17 . H172 . 108.681 no C16 . C17 . H173 . 110.078 no H171 . C17 . H173 . 108.031 no H172 . C17 . H173 . 109.212 no C16 . C18 . H181 . 111.278 no C16 . C18 . H182 . 109.833 no H181 . C18 . H182 . 109.273 no C16 . C18 . H183 . 109.729 no H181 . C18 . H183 . 108.670 no H182 . C18 . H183 . 107.988 no C15 . O19 . H191 . 109.823 no C14 . C20 . H201 . 110.074 no C14 . C20 . H202 . 110.004 no H201 . C20 . H202 . 108.723 no C14 . C20 . H203 . 109.515 no H201 . C20 . H203 . 109.241 no H202 . C20 . H203 . 109.263 no C23 . N22 . C27 . 120.4(2) yes C23 . N22 . C34 . 115.79(18) yes C27 . N22 . C34 . 123.6(2) yes N22 . C23 . C24 . 110.5(2) yes N22 . C23 . C31 . 109.50(18) yes C24 . C23 . C31 . 114.1(2) yes N22 . C23 . H231 . 109.790 no C24 . C23 . H231 . 105.572 no C31 . C23 . H231 . 107.214 no C23 . C24 . C25 . 111.8(2) yes C23 . C24 . H241 . 108.321 no C25 . C24 . H241 . 108.875 no C23 . C24 . H242 . 110.285 no C25 . C24 . H242 . 109.610 no H241 . C24 . H242 . 107.799 no C24 . C25 . O26 . 106.2(2) yes C24 . C25 . C29 . 114.3(3) yes O26 . C25 . C29 . 110.0(2) yes C24 . C25 . C30 . 111.7(3) yes O26 . C25 . C30 . 103.1(2) yes C29 . C25 . C30 . 110.9(3) yes C25 . O26 . C27 . 120.0(2) yes N22 . C27 . O26 . 116.3(2) yes N22 . C27 . O28 . 124.1(2) yes O26 . C27 . O28 . 119.7(2) yes C25 . C29 . H291 . 110.557 no C25 . C29 . H292 . 111.922 no H291 . C29 . H292 . 109.340 no C25 . C29 . H293 . 109.634 no H291 . C29 . H293 . 106.234 no H292 . C29 . H293 . 108.980 no C25 . C30 . H301 . 112.419 no C25 . C30 . H302 . 109.948 no H301 . C30 . H302 . 109.325 no C25 . C30 . H303 . 109.532 no H301 . C30 . H303 . 108.556 no H302 . C30 . H303 . 106.897 no C23 . C31 . C32 . 112.7(2) yes C23 . C31 . C33 . 110.8(2) yes C32 . C31 . C33 . 111.1(2) yes C23 . C31 . H311 . 107.279 no C32 . C31 . H311 . 105.536 no C33 . C31 . H311 . 109.165 no C31 . C32 . H321 . 110.973 no C31 . C32 . H322 . 109.687 no H321 . C32 . H322 . 110.154 no C31 . C32 . H323 . 109.411 no H321 . C32 . H323 . 108.739 no H322 . C32 . H323 . 107.811 no C31 . C33 . H331 . 110.001 no C31 . C33 . H332 . 109.634 no H331 . C33 . H332 . 107.563 no C31 . C33 . H333 . 111.141 no H331 . C33 . H333 . 109.067 no H332 . C33 . H333 . 109.359 no N22 . C34 . C35 . 121.6(2) yes N22 . C34 . O42 . 117.9(2) yes C35 . C34 . O42 . 120.4(2) yes C34 . C35 . C36 . 110.0(2) yes C34 . C35 . C41 . 106.3(2) yes C36 . C35 . C41 . 111.5(2) yes C34 . C35 . H351 . 112.144 no C36 . C35 . H351 . 105.678 no C41 . C35 . H351 . 111.285 no C35 . C36 . C37 . 113.2(2) yes C35 . C36 . O40 . 106.07(19) yes C37 . C36 . O40 . 110.8(2) yes C35 . C36 . H361 . 110.969 no C37 . C36 . H361 . 104.988 no O40 . C36 . H361 . 110.873 no C36 . C37 . C38 . 111.0(3) yes C36 . C37 . C39 . 111.4(3) yes C38 . C37 . C39 . 111.7(3) yes C36 . C37 . H371 . 108.177 no C38 . C37 . H371 . 108.928 no C39 . C37 . H371 . 105.461 no C37 . C38 . H381 . 111.954 no C37 . C38 . H382 . 108.667 no H381 . C38 . H382 . 108.383 no C37 . C38 . H383 . 110.589 no H381 . C38 . H383 . 109.598 no H382 . C38 . H383 . 107.518 no C37 . C39 . H391 . 107.815 no C37 . C39 . H392 . 108.069 no H391 . C39 . H392 . 109.394 no C37 . C39 . H393 . 109.761 no H391 . C39 . H393 . 109.467 no H392 . C39 . H393 . 112.226 no C36 . O40 . H401 . 113.211 no C35 . C41 . H411 . 110.966 no C35 . C41 . H412 . 109.315 no H411 . C41 . H412 . 108.923 no C35 . C41 . H413 . 109.456 no H411 . C41 . H413 . 110.044 no H412 . C41 . H413 . 108.080 no