Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Timothy Donohoe' 'Mark J. Bamford' 'Craig Banks' 'Jessica Y. K. Chiu' 'Richard Compton' 'Osamu Ichihara' 'Dale J. Johnson' 'Laura H Mace' 'Jason S. Rodrigues' 'Rhian E. Thomas' 'Peter Tomcik' _publ_contact_author_name 'Timothy Donohoe' _publ_contact_author_address ; Department of Chemistry University of Oxford Chemistry Research Laboratory Mansfield Road Oxford OX1 3TA UNITED KINGDOM ; _publ_contact_author_email TIMOTHY.DONOHOE@CHEM.OX.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; The Ammonia-Free Partial Reduction of Substituted Pyridinium Salts ; # Attachment '14cif.txt' data_arc722 _database_code_depnum_ccdc_archive 'CCDC 294438' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_special_details ; All hydrogen atoms were positioned geometrically, the preferred orientation of the N-methyl group having been previously determined by examination of a difference Fourier map ; #============================================================= _cell_length_a 7.1187(2) _cell_angle_alpha 90 _cell_length_b 12.4355(2) _cell_angle_beta 105.5450(8) _cell_length_c 10.6250(3) _cell_angle_gamma 90 _cell_volume 906.17(4) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 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 ' C9 H13 N1 O3 ' _chemical_formula_moiety ' C9 H13 N1 O3 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 183.21 _cell_measurement_reflns_used 12098 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.26 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 392.000 _exptl_absorpt_coefficient_mu 0.101 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.97 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 12098 _reflns_number_total 2070 #2169 unique data including absences _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_theta_min 5.160 _diffrn_reflns_theta_max 27.504 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.504 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -9 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _refine_diff_density_min -0.21 _refine_diff_density_max 0.27 _refine_ls_number_reflns 1581 _refine_ls_number_restraints 0 _refine_ls_number_parameters 118 #_refine_ls_R_factor_ref 0.0372 _refine_ls_wR_factor_ref 0.0459 _refine_ls_goodness_of_fit_ref 1.0774 #_reflns_number_all 2070 _refine_ls_R_factor_all 0.0502 _refine_ls_wR_factor_all 0.0539 # 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 1581 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_gt 0.0459 _refine_ls_shift/su_max 0.006516 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.731 0.432 0.389 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # 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 N1 N 0.44755(15) 0.09844(8) 0.1675(1) 0.0212 1.0000 Uani C1 C 0.62925(18) 0.13547(11) 0.21936(12) 0.0232 1.0000 Uani C2 C 0.67515(18) 0.24003(11) 0.25504(13) 0.0246 1.0000 Uani C3 C 0.53155(18) 0.3228(1) 0.21865(12) 0.0220 1.0000 Uani C4 C 0.33430(18) 0.2843(1) 0.13741(12) 0.0217 1.0000 Uani C5 C 0.28606(17) 0.1702(1) 0.17249(11) 0.0192 1.0000 Uani C6 C 0.4130(2) -0.01633(11) 0.14109(15) 0.0302 1.0000 Uani O1 O 0.56255(15) 0.41977(8) 0.2420(1) 0.0306 1.0000 Uani C7 C 0.0923(2) 0.13270(11) 0.08001(13) 0.0284 1.0000 Uani C8 C 0.25433(16) 0.1713(1) 0.31059(11) 0.0192 1.0000 Uani O2 O 0.16254(15) 0.24052(8) 0.3469(1) 0.0309 1.0000 Uani O3 O 0.32733(13) 0.08507(7) 0.38147(9) 0.0242 1.0000 Uani C9 C 0.2718(2) 0.07333(12) 0.50252(14) 0.0296 1.0000 Uani H11 H 0.7390 0.0828 0.2329 0.0291 1.0000 Uiso H21 H 0.8104 0.2586 0.3070 0.0298 1.0000 Uiso H41 H 0.2319 0.3343 0.1517 0.0258 1.0000 Uiso H42 H 0.3337 0.2857 0.0432 0.0258 1.0000 Uiso H61 H 0.5386 -0.0524 0.1414 0.0380 1.0000 Uiso H62 H 0.3592 -0.0490 0.2101 0.0380 1.0000 Uiso H63 H 0.3175 -0.0260 0.0537 0.0380 1.0000 Uiso H71 H -0.0141 0.1834 0.0860 0.0325 1.0000 Uiso H72 H 0.1039 0.1315 -0.0117 0.0325 1.0000 Uiso H73 H 0.0608 0.0588 0.1055 0.0325 1.0000 Uiso H91 H 0.3330 0.0069 0.5488 0.0373 1.0000 Uiso H92 H 0.3174 0.1374 0.5593 0.0373 1.0000 Uiso H93 H 0.1267 0.0676 0.4828 0.0373 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 0.0273(5) 0.0158(5) 0.0231(5) -0.0005(4) 0.0111(4) 0.0015(4) C1 0.0244(6) 0.0258(6) 0.0224(6) 0.0042(5) 0.0115(5) 0.0039(5) C2 0.0215(6) 0.0279(7) 0.0252(6) 0.0002(5) 0.0078(5) -0.0028(5) C3 0.0273(6) 0.0214(6) 0.0202(6) -0.0005(5) 0.0115(5) -0.0045(5) C4 0.0260(6) 0.0171(6) 0.0213(6) 0.0018(4) 0.0053(5) 0.0006(5) C5 0.0209(5) 0.0174(5) 0.0192(5) 0.0005(4) 0.0053(4) 0.0010(4) C6 0.0436(8) 0.0168(6) 0.0346(7) -0.0029(5) 0.0181(6) -0.0008(5) O1 0.0382(5) 0.0209(5) 0.0353(5) -0.0045(4) 0.0142(4) -0.0077(4) C7 0.0285(7) 0.0268(7) 0.0260(7) -0.0002(5) 0.0006(5) -0.0046(5) C8 0.0172(5) 0.0179(6) 0.0224(6) -0.0006(4) 0.0052(4) -0.0017(4) O2 0.0361(5) 0.0271(5) 0.0338(5) 0.0012(4) 0.0169(4) 0.0093(4) O3 0.0311(5) 0.0232(5) 0.0219(5) 0.0048(3) 0.0132(4) 0.0061(4) C9 0.0388(7) 0.0319(7) 0.0224(6) 0.0040(5) 0.0156(5) 0.0026(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 . C1 . 1.3442(17) yes N1 . C5 . 1.4673(15) yes N1 . C6 . 1.4625(17) yes C1 . C2 . 1.3692(19) yes C1 . H11 . 1.000 no C2 . C3 . 1.4293(18) yes C2 . H21 . 1.000 no C3 . C4 . 1.5156(17) yes C3 . O1 . 1.2385(16) yes C4 . C5 . 1.5293(17) yes C4 . H41 . 1.000 no C4 . H42 . 1.000 no C5 . C7 . 1.5361(17) yes C5 . C8 . 1.5434(17) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C6 . H63 . 1.000 no C7 . H71 . 1.000 no C7 . H72 . 1.000 no C7 . H73 . 1.000 no C8 . O2 . 1.2051(16) yes C8 . O3 . 1.3327(15) yes O3 . C9 . 1.4506(16) yes C9 . H91 . 1.000 no C9 . H92 . 1.000 no C9 . H93 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C5 . 117.0(1) yes C1 . N1 . C6 . 120.46(11) yes C5 . N1 . C6 . 120.47(11) yes N1 . C1 . C2 . 124.81(12) yes N1 . C1 . H11 . 117.595 no C2 . C1 . H11 . 117.595 no C1 . C2 . C3 . 120.59(11) yes C1 . C2 . H21 . 119.703 no C3 . C2 . H21 . 119.703 no C2 . C3 . C4 . 114.36(11) yes C2 . C3 . O1 . 124.82(12) yes C4 . C3 . O1 . 120.66(12) yes C3 . C4 . C5 . 112.9(1) yes C3 . C4 . H41 . 108.611 no C5 . C4 . H41 . 108.611 no C3 . C4 . H42 . 108.612 no C5 . C4 . H42 . 108.611 no H41 . C4 . H42 . 109.466 no N1 . C5 . C4 . 109.0(1) yes N1 . C5 . C7 . 111.7(1) yes C4 . C5 . C7 . 110.3(1) yes N1 . C5 . C8 . 110.81(9) yes C4 . C5 . C8 . 108.9(1) yes C7 . C5 . C8 . 106.0(1) yes N1 . C6 . H61 . 109.467 no N1 . C6 . H62 . 109.467 no H61 . C6 . H62 . 109.476 no N1 . C6 . H63 . 109.466 no H61 . C6 . H63 . 109.475 no H62 . C6 . H63 . 109.476 no C5 . C7 . H71 . 109.466 no C5 . C7 . H72 . 109.467 no H71 . C7 . H72 . 109.475 no C5 . C7 . H73 . 109.467 no H71 . C7 . H73 . 109.475 no H72 . C7 . H73 . 109.476 no C5 . C8 . O2 . 122.69(11) yes C5 . C8 . O3 . 113.3(1) yes O2 . C8 . O3 . 123.84(12) yes C8 . O3 . C9 . 115.1(1) yes O3 . C9 . H91 . 109.467 no O3 . C9 . H92 . 109.467 no H91 . C9 . H92 . 109.475 no O3 . C9 . H93 . 109.467 no H91 . C9 . H93 . 109.475 no H92 . C9 . H93 . 109.476 no # Attachment '35cif.txt' data_ARC813 _database_code_depnum_ccdc_archive 'CCDC 294439' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref #============================================================= _cell_length_a 8.0683(2) _cell_angle_alpha 90 _cell_length_b 10.3413(2) _cell_angle_beta 100.6130(9) _cell_length_c 20.1216(4) _cell_angle_gamma 90 _cell_volume 1650.16(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 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 H23 N1 O4 ' _chemical_formula_moiety ' C19 H23 N1 O4 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 329.40 _cell_measurement_reflns_used 13884 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.32 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.093 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.97 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 13884 _reflns_number_total 3656 #3852 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_theta_min 5.142 _diffrn_reflns_theta_max 27.472 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.823 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _refine_diff_density_min -0.18 _refine_diff_density_max 0.29 _refine_ls_number_reflns 2772 _refine_ls_number_restraints 0 _refine_ls_number_parameters 217 #_refine_ls_R_factor_ref 0.0397 _refine_ls_wR_factor_ref 0.0463 _refine_ls_goodness_of_fit_ref 1.0912 #_reflns_number_all 3656 _refine_ls_R_factor_all 0.0560 _refine_ls_wR_factor_all 0.0521 # 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 2772 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_gt 0.0463 _refine_ls_shift/su_max 0.002929 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.12 0.303 0.655 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # 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 N1 N 0.37957(13) 0.55947(10) 0.10769(5) 0.0171 1.0000 Uani C1 C 0.49902(17) 0.48372(12) 0.08846(7) 0.0201 1.0000 Uani C2 C 0.66891(17) 0.50319(13) 0.10474(7) 0.0226 1.0000 Uani C3 C 0.73616(17) 0.60204(13) 0.15219(7) 0.0204 1.0000 Uani C4 C 0.60598(17) 0.67007(12) 0.18503(7) 0.0192 1.0000 Uani C5 C 0.57578(18) 0.59341(14) 0.24708(7) 0.0243 1.0000 Uani C6 C 0.4541(2) 0.66499(17) 0.28369(8) 0.0323 1.0000 Uani C7 C 0.28704(19) 0.69126(17) 0.23600(8) 0.0317 1.0000 Uani C8 C 0.31246(18) 0.75823(14) 0.17113(8) 0.0260 1.0000 Uani C9 C 0.43783(16) 0.68741(12) 0.13494(7) 0.0187 1.0000 Uani C10 C 0.20007(16) 0.53419(13) 0.07793(7) 0.0210 1.0000 Uani C11 C 0.15130(16) 0.39418(13) 0.08557(7) 0.0197 1.0000 Uani C12 C 0.10688(17) 0.35143(13) 0.14542(7) 0.0217 1.0000 Uani C13 C 0.06032(17) 0.22347(13) 0.15383(7) 0.0221 1.0000 Uani C14 C 0.05850(17) 0.13629(13) 0.10120(7) 0.0233 1.0000 Uani C15 C 0.1012(2) 0.17730(15) 0.04045(8) 0.0294 1.0000 Uani C16 C 0.14655(19) 0.30520(15) 0.03314(7) 0.0265 1.0000 Uani O1 O 0.01642(15) 0.00811(10) 0.10409(6) 0.0327 1.0000 Uani C17 C -0.0485(2) -0.03443(15) 0.16174(8) 0.0301 1.0000 Uani O2 O 0.88756(12) 0.62641(11) 0.17003(6) 0.0294 1.0000 Uani C18 C 0.46868(18) 0.77918(13) 0.07785(7) 0.0235 1.0000 Uani O3 O 0.55973(17) 0.87177(12) 0.08746(6) 0.0450 1.0000 Uani O4 O 0.37611(13) 0.74886(10) 0.01815(5) 0.0271 1.0000 Uani C19 C 0.3846(2) 0.84023(16) -0.03589(8) 0.0338 1.0000 Uani H11 H 0.4594 0.4068 0.0598 0.0242 1.0000 Uiso H21 H 0.7470 0.4483 0.0835 0.0276 1.0000 Uiso H41 H 0.6506 0.7579 0.1994 0.0230 1.0000 Uiso H51 H 0.6857 0.5813 0.2787 0.0289 1.0000 Uiso H52 H 0.5271 0.5070 0.2321 0.0289 1.0000 Uiso H61 H 0.5057 0.7491 0.3011 0.0392 1.0000 Uiso H62 H 0.4323 0.6111 0.3225 0.0392 1.0000 Uiso H71 H 0.2158 0.7478 0.2597 0.0393 1.0000 Uiso H72 H 0.2280 0.6071 0.2240 0.0393 1.0000 Uiso H81 H 0.3557 0.8476 0.1826 0.0315 1.0000 Uiso H82 H 0.2011 0.7632 0.1397 0.0315 1.0000 Uiso H101 H 0.1274 0.5903 0.1012 0.0247 1.0000 Uiso H102 H 0.1808 0.5562 0.0287 0.0247 1.0000 Uiso H121 H 0.1084 0.4140 0.1834 0.0263 1.0000 Uiso H131 H 0.0286 0.1948 0.1973 0.0270 1.0000 Uiso H151 H 0.0992 0.1148 0.0024 0.0355 1.0000 Uiso H161 H 0.1764 0.3342 -0.0106 0.0318 1.0000 Uiso H171 H -0.0739 -0.1290 0.1576 0.0366 1.0000 Uiso H172 H 0.0371 -0.0183 0.2036 0.0366 1.0000 Uiso H173 H -0.1542 0.0142 0.1644 0.0366 1.0000 Uiso H191 H 0.3114 0.8094 -0.0785 0.0399 1.0000 Uiso H192 H 0.3445 0.9269 -0.0234 0.0399 1.0000 Uiso H193 H 0.5037 0.8473 -0.0429 0.0399 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 0.0145(5) 0.0160(5) 0.0205(5) 0.0011(4) 0.0026(4) -0.0018(4) C1 0.0227(7) 0.0177(6) 0.0202(6) -0.0012(5) 0.0049(5) -0.0006(5) C2 0.0199(7) 0.0221(7) 0.0269(7) -0.0037(5) 0.0072(5) 0.0016(5) C3 0.0184(6) 0.0202(6) 0.0229(6) 0.0024(5) 0.0049(5) -0.0006(5) C4 0.0184(6) 0.0192(6) 0.0198(6) -0.0013(5) 0.0030(5) -0.0017(5) C5 0.0247(7) 0.0279(7) 0.0197(6) 0.0021(5) 0.0019(5) -0.0040(5) C6 0.0319(8) 0.0433(9) 0.0229(7) -0.0054(6) 0.0078(6) -0.0077(7) C7 0.0254(8) 0.0416(9) 0.0311(8) -0.0094(7) 0.0129(6) -0.0029(6) C8 0.0221(7) 0.0235(7) 0.0331(7) -0.0076(6) 0.0072(6) 0.0026(5) C9 0.0199(6) 0.0163(6) 0.0199(6) -0.0010(5) 0.0037(5) 0.0006(5) C10 0.0158(6) 0.0213(6) 0.0246(6) 0.0033(5) 0.0001(5) -0.0024(5) C11 0.0137(6) 0.0211(6) 0.0231(6) 0.0021(5) 0.0005(5) -0.0010(5) C12 0.0201(6) 0.0211(6) 0.0244(6) -0.0018(5) 0.0060(5) 0.0000(5) C13 0.0207(7) 0.0223(7) 0.0246(6) 0.0018(5) 0.0070(5) -0.0007(5) C14 0.0191(7) 0.0201(6) 0.0306(7) -0.0010(5) 0.0043(5) -0.0034(5) C15 0.0327(8) 0.0294(8) 0.0268(7) -0.0085(6) 0.0072(6) -0.0089(6) C16 0.0271(7) 0.0306(7) 0.0217(6) -0.0005(6) 0.0041(5) -0.0076(6) O1 0.0423(7) 0.0199(5) 0.0392(6) -0.0051(4) 0.0159(5) -0.0092(4) C17 0.0275(8) 0.0227(7) 0.0414(9) 0.0019(6) 0.0101(6) -0.0037(6) O2 0.0170(5) 0.0314(6) 0.0395(6) -0.0058(5) 0.0044(4) -0.0029(4) C18 0.0256(7) 0.0183(6) 0.0259(7) 0.0029(5) 0.0032(5) 0.0003(5) O3 0.0560(8) 0.0330(6) 0.0393(7) 0.0126(5) -0.0086(6) -0.0238(6) O4 0.0336(6) 0.0242(5) 0.0220(5) 0.0064(4) 0.0011(4) -0.0049(4) C19 0.0400(9) 0.0311(8) 0.0287(8) 0.0134(6) 0.0018(7) -0.0035(7) _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 . C1 . 1.3527(17) yes N1 . C9 . 1.4755(16) yes N1 . C10 . 1.4848(16) yes C1 . C2 . 1.3643(19) yes C1 . H11 . 1.000 no C2 . C3 . 1.4353(19) yes C2 . H21 . 1.000 no C3 . C4 . 1.5134(18) yes C3 . O2 . 1.2341(17) yes C4 . C5 . 1.5358(19) yes C4 . C9 . 1.5443(18) yes C4 . H41 . 1.000 no C5 . C6 . 1.524(2) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C6 . C7 . 1.528(2) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . C8 . 1.524(2) yes C7 . H71 . 1.000 no C7 . H72 . 1.000 no C8 . C9 . 1.5366(18) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no C9 . C18 . 1.5451(19) yes C10 . C11 . 1.5156(18) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C11 . C12 . 1.3903(19) yes C11 . C16 . 1.395(2) yes C12 . C13 . 1.3944(19) yes C12 . H121 . 1.000 no C13 . C14 . 1.389(2) yes C13 . H131 . 1.000 no C14 . C15 . 1.396(2) yes C14 . O1 . 1.3722(17) yes C15 . C16 . 1.387(2) yes C15 . H151 . 1.000 no C16 . H161 . 1.000 no O1 . C17 . 1.4273(19) yes C17 . H171 . 1.000 no C17 . H172 . 1.000 no C17 . H173 . 1.000 no C18 . O3 . 1.2007(18) yes C18 . O4 . 1.3301(17) yes O4 . C19 . 1.4516(17) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C9 . 115.50(10) yes C1 . N1 . C10 . 118.43(11) yes C9 . N1 . C10 . 121.87(10) yes N1 . C1 . C2 . 125.67(12) yes N1 . C1 . H11 . 117.164 no C2 . C1 . H11 . 117.164 no C1 . C2 . C3 . 120.32(12) yes C1 . C2 . H21 . 119.839 no C3 . C2 . H21 . 119.839 no C2 . C3 . C4 . 114.44(11) yes C2 . C3 . O2 . 124.87(12) yes C4 . C3 . O2 . 120.49(12) yes C3 . C4 . C5 . 109.99(11) yes C3 . C4 . C9 . 111.47(11) yes C5 . C4 . C9 . 109.79(11) yes C3 . C4 . H41 . 107.867 no C5 . C4 . H41 . 109.606 no C9 . C4 . H41 . 108.069 no C4 . C5 . C6 . 110.81(12) yes C4 . C5 . H51 . 109.138 no C6 . C5 . H51 . 109.138 no C4 . C5 . H52 . 109.138 no C6 . C5 . H52 . 109.138 no H51 . C5 . H52 . 109.467 no C5 . C6 . C7 . 110.81(12) yes C5 . C6 . H61 . 109.137 no C7 . C6 . H61 . 109.138 no C5 . C6 . H62 . 109.137 no C7 . C6 . H62 . 109.138 no H61 . C6 . H62 . 109.467 no C6 . C7 . C8 . 112.11(12) yes C6 . C7 . H71 . 108.810 no C8 . C7 . H71 . 108.809 no C6 . C7 . H72 . 108.810 no C8 . C7 . H72 . 108.810 no H71 . C7 . H72 . 109.467 no C7 . C8 . C9 . 113.16(12) yes C7 . C8 . H81 . 108.542 no C9 . C8 . H81 . 108.542 no C7 . C8 . H82 . 108.542 no C9 . C8 . H82 . 108.542 no H81 . C8 . H82 . 109.467 no N1 . C9 . C4 . 108.65(10) yes N1 . C9 . C8 . 114.27(11) yes C4 . C9 . C8 . 108.78(11) yes N1 . C9 . C18 . 111.00(10) yes C4 . C9 . C18 . 108.30(11) yes C8 . C9 . C18 . 105.65(11) yes N1 . C10 . C11 . 112.30(11) yes N1 . C10 . H101 . 108.761 no C11 . C10 . H101 . 108.760 no N1 . C10 . H102 . 108.760 no C11 . C10 . H102 . 108.760 no H101 . C10 . H102 . 109.467 no C10 . C11 . C12 . 120.32(12) yes C10 . C11 . C16 . 121.66(12) yes C12 . C11 . C16 . 118.01(12) yes C11 . C12 . C13 . 121.68(12) yes C11 . C12 . H121 . 119.162 no C13 . C12 . H121 . 119.162 no C12 . C13 . C14 . 119.26(12) yes C12 . C13 . H131 . 120.370 no C14 . C13 . H131 . 120.371 no C13 . C14 . C15 . 120.06(13) yes C13 . C14 . O1 . 124.25(13) yes C15 . C14 . O1 . 115.69(13) yes C14 . C15 . C16 . 119.66(13) yes C14 . C15 . H151 . 120.169 no C16 . C15 . H151 . 120.169 no C11 . C16 . C15 . 121.32(13) yes C11 . C16 . H161 . 119.339 no C15 . C16 . H161 . 119.339 no C14 . O1 . C17 . 117.57(11) yes O1 . C17 . H171 . 109.467 no O1 . C17 . H172 . 109.467 no H171 . C17 . H172 . 109.476 no O1 . C17 . H173 . 109.467 no H171 . C17 . H173 . 109.476 no H172 . C17 . H173 . 109.476 no C9 . C18 . O3 . 123.21(13) yes C9 . C18 . O4 . 112.72(11) yes O3 . C18 . O4 . 123.95(13) yes C18 . O4 . C19 . 115.28(11) yes O4 . C19 . H191 . 109.467 no O4 . C19 . H192 . 109.467 no H191 . C19 . H192 . 109.476 no O4 . C19 . H193 . 109.467 no H191 . C19 . H193 . 109.476 no H192 . C19 . H193 . 109.476 no