# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_C12H21NO3compound25 _database_code_depnum_ccdc_archive 'CCDC 726211' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common quinolizidine _chemical_melting_point '133-134 degree centigrade' _chemical_formula_moiety 'C12 H21 N O3' _chemical_formula_sum 'C12 H21 N O3' _chemical_formula_weight 227.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.7250(11) _cell_length_b 6.4790(7) _cell_length_c 20.325(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1280.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1004 _cell_measurement_theta_min 2.322 _cell_measurement_theta_max 17.494 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9833 _exptl_absorpt_correction_T_max 0.9990 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10685 _diffrn_reflns_av_R_equivalents 0.0745 _diffrn_reflns_av_sigmaI/netI 0.0671 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2250 _reflns_number_gt 1251 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, PyMOL and PLATON' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.5(18) _refine_ls_number_reflns 2250 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1121 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8765(2) 0.4920(4) 0.62078(10) 0.0771(7) Uani 1 1 d . . . C2 C 0.8435(4) 0.5802(6) 0.55755(17) 0.0884(11) Uani 1 1 d . . . O3 O 0.7887(2) 0.7825(4) 0.56891(10) 0.0913(8) Uani 1 1 d . . . C3A C 0.8155(3) 0.8266(5) 0.63636(13) 0.0667(9) Uani 1 1 d . . . H3A H 0.9095 0.8787 0.6412 0.080 Uiso 1 1 calc R . . C4 C 0.7162(3) 0.9730(5) 0.66944(14) 0.0723(9) Uani 1 1 d . . . H4A H 0.7242 1.1099 0.6505 0.087 Uiso 1 1 calc R . . H4B H 0.6225 0.9253 0.6636 0.087 Uiso 1 1 calc R . . N5 N 0.7515(2) 0.9783(4) 0.73980(11) 0.0566(6) Uani 1 1 d . . . C6 C 0.6537(3) 1.1152(5) 0.77323(16) 0.0742(10) Uani 1 1 d . . . H6A H 0.5619 1.0581 0.7693 0.089 Uiso 1 1 calc R . . H6B H 0.6541 1.2488 0.7517 0.089 Uiso 1 1 calc R . . C7 C 0.6879(3) 1.1432(6) 0.84488(16) 0.0823(10) Uani 1 1 d . . . H7A H 0.6197 1.2315 0.8653 0.099 Uiso 1 1 calc R . . H7B H 0.7769 1.2096 0.8490 0.099 Uiso 1 1 calc R . . C8 C 0.6909(4) 0.9372(6) 0.87955(16) 0.0879(11) Uani 1 1 d . . . H8A H 0.5994 0.8776 0.8800 0.106 Uiso 1 1 calc R . . H8B H 0.7206 0.9556 0.9247 0.106 Uiso 1 1 calc R . . C9 C 0.7896(3) 0.7930(5) 0.84386(13) 0.0681(9) Uani 1 1 d . . . H9B H 0.8825 0.8461 0.8478 0.082 Uiso 1 1 calc R . . H9C H 0.7870 0.6581 0.8645 0.082 Uiso 1 1 calc R . . C9A C 0.7533(3) 0.7718(4) 0.77212(13) 0.0534(7) Uani 1 1 d . . . H9A H 0.6604 0.7137 0.7693 0.064 Uiso 1 1 calc R . . C10 C 0.8523(3) 0.6234(4) 0.73643(14) 0.0576(8) Uani 1 1 d . . . H10 H 0.8462 0.4852 0.7558 0.069 Uiso 1 1 calc R . . C10A C 0.8050(3) 0.6185(5) 0.66639(14) 0.0599(8) Uani 1 1 d . . . H10A H 0.7080 0.5775 0.6660 0.072 Uiso 1 1 calc R . . O2 O 0.98896(17) 0.6998(3) 0.74178(10) 0.0624(6) Uani 1 1 d . . . H2 H 1.0420 0.6031 0.7476 0.094 Uiso 1 1 calc R . . C11 C 0.9755(5) 0.5919(7) 0.51835(17) 0.1450(19) Uani 1 1 d . . . H11A H 1.0370 0.6885 0.5388 0.218 Uiso 1 1 calc R . . H11B H 0.9555 0.6364 0.4743 0.218 Uiso 1 1 calc R . . H11C H 1.0179 0.4581 0.5171 0.218 Uiso 1 1 calc R . . C12 C 0.7326(4) 0.4504(7) 0.52468(17) 0.1214(15) Uani 1 1 d . . . H12A H 0.7658 0.3122 0.5186 0.182 Uiso 1 1 calc R . . H12B H 0.7100 0.5092 0.4827 0.182 Uiso 1 1 calc R . . H12C H 0.6521 0.4480 0.5520 0.182 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0870(16) 0.0763(16) 0.0680(14) -0.0097(13) -0.0086(11) 0.0083(14) C2 0.100(3) 0.101(3) 0.065(2) -0.005(2) -0.015(2) 0.002(2) O3 0.1134(19) 0.091(2) 0.0701(16) 0.0035(14) -0.0245(13) 0.0058(15) C3A 0.071(2) 0.073(3) 0.056(2) 0.0098(18) -0.0156(16) -0.0066(19) C4 0.0650(19) 0.062(2) 0.090(2) 0.0134(19) -0.0260(17) -0.0011(19) N5 0.0445(12) 0.0527(15) 0.0725(16) 0.0033(14) -0.0051(11) 0.0046(12) C6 0.0464(16) 0.064(2) 0.112(3) 0.0007(19) -0.0056(18) 0.0031(16) C7 0.069(2) 0.073(3) 0.105(3) -0.011(2) 0.0150(19) 0.0110(19) C8 0.083(2) 0.090(3) 0.091(2) 0.001(2) 0.0224(19) 0.005(2) C9 0.070(2) 0.061(2) 0.073(2) 0.0031(18) 0.0059(16) 0.0027(18) C9A 0.0431(15) 0.0461(19) 0.0711(19) 0.0078(15) -0.0038(14) -0.0053(14) C10 0.0481(15) 0.0495(18) 0.075(2) 0.0052(16) -0.0099(15) -0.0048(15) C10A 0.0546(18) 0.059(2) 0.066(2) -0.0012(18) -0.0069(15) -0.0019(16) O2 0.0454(10) 0.0580(12) 0.0839(13) 0.0021(12) -0.0094(10) 0.0050(10) C11 0.130(4) 0.216(6) 0.090(3) 0.028(3) 0.027(3) 0.027(4) C12 0.140(3) 0.123(4) 0.101(3) -0.037(3) -0.042(2) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10A 1.419(3) . ? O1 C2 1.443(4) . ? C2 O3 1.434(4) . ? C2 C11 1.513(5) . ? C2 C12 1.522(5) . ? O3 C3A 1.424(3) . ? C3A C10A 1.484(4) . ? C3A C4 1.511(4) . ? C3A H3A 0.9800 . ? C4 N5 1.471(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N5 C6 1.467(3) . ? N5 C9A 1.491(3) . ? C6 C7 1.505(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.509(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.523(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C9A 1.506(3) . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C9A C10 1.542(3) . ? C9A H9A 0.9800 . ? C10 O2 1.422(3) . ? C10 C10A 1.496(3) . ? C10 H10 0.9800 . ? C10A H10A 0.9800 . ? O2 H2 0.8200 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10A O1 C2 104.1(2) . . ? O3 C2 O1 107.5(3) . . ? O3 C2 C11 110.7(3) . . ? O1 C2 C11 107.5(3) . . ? O3 C2 C12 108.2(3) . . ? O1 C2 C12 109.3(3) . . ? C11 C2 C12 113.4(3) . . ? C3A O3 C2 105.7(2) . . ? O3 C3A C10A 101.6(3) . . ? O3 C3A C4 116.0(2) . . ? C10A C3A C4 110.1(3) . . ? O3 C3A H3A 109.6 . . ? C10A C3A H3A 109.6 . . ? C4 C3A H3A 109.6 . . ? N5 C4 C3A 107.4(2) . . ? N5 C4 H4A 110.2 . . ? C3A C4 H4A 110.2 . . ? N5 C4 H4B 110.2 . . ? C3A C4 H4B 110.2 . . ? H4A C4 H4B 108.5 . . ? C6 N5 C4 108.3(2) . . ? C6 N5 C9A 110.2(2) . . ? C4 N5 C9A 114.2(2) . . ? N5 C6 C7 112.2(2) . . ? N5 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? N5 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C6 C7 C8 110.5(3) . . ? C6 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? C6 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C7 C8 C9 109.4(3) . . ? C7 C8 H8A 109.8 . . ? C9 C8 H8A 109.8 . . ? C7 C8 H8B 109.8 . . ? C9 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C9A C9 C8 111.7(3) . . ? C9A C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? C9A C9 H9C 109.3 . . ? C8 C9 H9C 109.3 . . ? H9B C9 H9C 107.9 . . ? N5 C9A C9 110.3(2) . . ? N5 C9A C10 111.1(2) . . ? C9 C9A C10 111.5(2) . . ? N5 C9A H9A 107.9 . . ? C9 C9A H9A 107.9 . . ? C10 C9A H9A 107.9 . . ? O2 C10 C10A 111.5(2) . . ? O2 C10 C9A 109.3(2) . . ? C10A C10 C9A 105.6(2) . . ? O2 C10 H10 110.1 . . ? C10A C10 H10 110.1 . . ? C9A C10 H10 110.1 . . ? O1 C10A C3A 102.9(2) . . ? O1 C10A C10 118.9(2) . . ? C3A C10A C10 110.6(2) . . ? O1 C10A H10A 108.0 . . ? C3A C10A H10A 108.0 . . ? C10 C10A H10A 108.0 . . ? C10 O2 H2 109.5 . . ? C2 C11 H11A 109.5 . . ? C2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C2 C12 H12A 109.5 . . ? C2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10A O1 C2 O3 16.0(3) . . . . ? C10A O1 C2 C11 135.3(3) . . . . ? C10A O1 C2 C12 -101.3(3) . . . . ? O1 C2 O3 C3A 11.3(4) . . . . ? C11 C2 O3 C3A -105.9(3) . . . . ? C12 C2 O3 C3A 129.2(3) . . . . ? C2 O3 C3A C10A -32.7(3) . . . . ? C2 O3 C3A C4 -152.0(3) . . . . ? O3 C3A C4 N5 173.3(2) . . . . ? C10A C3A C4 N5 58.7(3) . . . . ? C3A C4 N5 C6 -178.4(2) . . . . ? C3A C4 N5 C9A -55.2(3) . . . . ? C4 N5 C6 C7 -175.7(3) . . . . ? C9A N5 C6 C7 58.7(3) . . . . ? N5 C6 C7 C8 -57.7(3) . . . . ? C6 C7 C8 C9 54.6(4) . . . . ? C7 C8 C9 C9A -55.4(4) . . . . ? C6 N5 C9A C9 -57.6(3) . . . . ? C4 N5 C9A C9 -179.7(2) . . . . ? C6 N5 C9A C10 178.3(2) . . . . ? C4 N5 C9A C10 56.2(3) . . . . ? C8 C9 C9A N5 56.9(3) . . . . ? C8 C9 C9A C10 -179.2(2) . . . . ? N5 C9A C10 O2 64.0(3) . . . . ? C9 C9A C10 O2 -59.5(3) . . . . ? N5 C9A C10 C10A -56.1(3) . . . . ? C9 C9A C10 C10A -179.6(2) . . . . ? C2 O1 C10A C3A -35.9(3) . . . . ? C2 O1 C10A C10 -158.4(3) . . . . ? O3 C3A C10A O1 42.9(3) . . . . ? C4 C3A C10A O1 166.3(2) . . . . ? O3 C3A C10A C10 170.8(2) . . . . ? C4 C3A C10A C10 -65.7(3) . . . . ? O2 C10 C10A O1 61.9(3) . . . . ? C9A C10 C10A O1 -179.5(2) . . . . ? O2 C10 C10A C3A -56.8(3) . . . . ? C9A C10 C10A C3A 61.9(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.101 _refine_diff_density_min -0.101 _refine_diff_density_rms 0.027 data_C13H23NO4compound23 _database_code_depnum_ccdc_archive 'CCDC 726212' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common quinolizidine _chemical_melting_point '135-136 degree centigrade' _chemical_formula_moiety 'C13 H23 N O4' _chemical_formula_sum 'C13 H23 N O4' _chemical_formula_weight 257.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.3743(4) _cell_length_b 10.2506(7) _cell_length_c 24.3106(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1339.27(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3392 _cell_measurement_theta_min 2.599 _cell_measurement_theta_max 25.246 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9793 _exptl_absorpt_correction_T_max 0.9990 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12741 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2369 _reflns_number_gt 2067 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, PyMOL and PLATON' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.0990P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(11) _refine_ls_number_reflns 2369 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0856 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7933(2) -0.16402(12) 0.07612(6) 0.0445(3) Uani 1 1 d . . . C2 C 0.6961(4) -0.28757(18) 0.09738(8) 0.0431(5) Uani 1 1 d . . . O3 O 0.5145(2) -0.25258(12) 0.13955(5) 0.0425(3) Uani 1 1 d . . . C3A C 0.4512(3) -0.11843(16) 0.12911(8) 0.0334(4) Uani 1 1 d . . . H3A H 0.3316 -0.1121 0.0988 0.040 Uiso 1 1 calc R . . C4 C 0.3598(3) -0.04334(18) 0.17843(7) 0.0373(4) Uani 1 1 d . . . H4A H 0.2035 -0.0793 0.1914 0.045 Uiso 1 1 calc R . . H4B H 0.4803 -0.0482 0.2081 0.045 Uiso 1 1 calc R . . N5 N 0.3254(3) 0.09389(14) 0.16083(6) 0.0323(3) Uani 1 1 d . . . C6 C 0.2430(4) 0.1704(2) 0.20986(7) 0.0438(5) Uani 1 1 d . . . H6A H 0.3708 0.1660 0.2380 0.053 Uiso 1 1 calc R . . H6B H 0.0930 0.1314 0.2247 0.053 Uiso 1 1 calc R . . C7 C 0.1918(4) 0.3132(2) 0.19610(8) 0.0485(5) Uani 1 1 d . . . H7A H 0.0527 0.3186 0.1708 0.058 Uiso 1 1 calc R . . H7B H 0.1469 0.3597 0.2294 0.058 Uiso 1 1 calc R . . C8 C 0.4190(4) 0.3769(2) 0.17034(8) 0.0467(5) Uani 1 1 d . . . H8A H 0.5517 0.3825 0.1973 0.056 Uiso 1 1 calc R . . H8B H 0.3779 0.4647 0.1585 0.056 Uiso 1 1 calc R . . C9 C 0.5058(3) 0.29610(17) 0.12083(7) 0.0382(4) Uani 1 1 d . . . H9B H 0.6554 0.3346 0.1056 0.046 Uiso 1 1 calc R . . H9C H 0.3782 0.2974 0.0926 0.046 Uiso 1 1 calc R . . C9A C 0.5591(3) 0.15412(17) 0.13763(7) 0.0309(4) Uani 1 1 d . . . H9A H 0.6804 0.1574 0.1677 0.037 Uiso 1 1 calc R . . C10 C 0.6833(3) 0.07373(17) 0.08952(7) 0.0306(4) Uani 1 1 d . . . C10A C 0.7008(3) -0.06430(17) 0.11190(7) 0.0333(4) Uani 1 1 d . . . H10A H 0.8078 -0.0621 0.1445 0.040 Uiso 1 1 calc R . . O2 O 0.9261(2) 0.12660(12) 0.07924(5) 0.0372(3) Uani 1 1 d . . . H2 H 1.0172 0.1108 0.1055 0.056 Uiso 1 1 calc R . . O4 O 0.6106(2) 0.19303(14) 0.00335(5) 0.0455(4) Uani 1 1 d . . . H4 H 0.4836 0.2299 -0.0070 0.068 Uiso 1 1 calc R . . C11 C 0.5456(3) 0.07945(17) 0.03395(7) 0.0333(4) Uani 1 1 d . . . H11A H 0.5864 0.0025 0.0126 0.040 Uiso 1 1 calc R . . H11B H 0.3676 0.0791 0.0405 0.040 Uiso 1 1 calc R . . C12 C 0.5718(5) -0.3589(2) 0.05020(9) 0.0584(6) Uani 1 1 d . . . H12A H 0.4303 -0.3098 0.0378 0.088 Uiso 1 1 calc R . . H12B H 0.5184 -0.4435 0.0624 0.088 Uiso 1 1 calc R . . H12C H 0.6878 -0.3686 0.0205 0.088 Uiso 1 1 calc R . . C13 C 0.9007(4) -0.3640(2) 0.12507(10) 0.0574(6) Uani 1 1 d . . . H13A H 1.0163 -0.3944 0.0979 0.086 Uiso 1 1 calc R . . H13B H 0.8301 -0.4372 0.1441 0.086 Uiso 1 1 calc R . . H13C H 0.9857 -0.3089 0.1509 0.086 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0454(7) 0.0318(7) 0.0564(8) 0.0077(6) 0.0174(7) 0.0046(6) C2 0.0400(11) 0.0337(10) 0.0557(11) 0.0096(9) 0.0058(10) 0.0007(9) O3 0.0400(8) 0.0341(7) 0.0533(8) 0.0130(6) 0.0096(6) 0.0000(6) C3A 0.0290(9) 0.0334(10) 0.0378(9) 0.0098(8) 0.0018(8) -0.0005(8) C4 0.0309(10) 0.0446(11) 0.0364(10) 0.0129(8) 0.0022(8) -0.0037(8) N5 0.0267(7) 0.0379(8) 0.0325(7) 0.0026(6) 0.0028(6) -0.0007(7) C6 0.0369(11) 0.0582(13) 0.0363(10) -0.0032(9) 0.0049(8) -0.0038(9) C7 0.0434(11) 0.0518(12) 0.0503(12) -0.0149(10) 0.0054(10) 0.0012(10) C8 0.0440(11) 0.0443(12) 0.0518(12) -0.0108(9) -0.0031(10) -0.0007(9) C9 0.0378(10) 0.0353(10) 0.0416(10) -0.0019(8) -0.0009(8) -0.0024(8) C9A 0.0248(8) 0.0378(10) 0.0301(8) 0.0015(8) -0.0043(7) -0.0039(8) C10 0.0222(8) 0.0345(9) 0.0352(9) 0.0054(8) 0.0035(7) -0.0019(8) C10A 0.0278(9) 0.0369(10) 0.0353(9) 0.0073(8) 0.0013(8) 0.0022(8) O2 0.0240(6) 0.0448(7) 0.0426(7) 0.0126(6) -0.0012(6) -0.0050(6) O4 0.0371(7) 0.0520(9) 0.0475(8) 0.0232(7) -0.0003(6) 0.0040(6) C11 0.0317(9) 0.0356(10) 0.0325(9) 0.0036(8) 0.0009(8) 0.0014(8) C12 0.0602(13) 0.0528(13) 0.0622(14) 0.0006(11) 0.0031(12) -0.0028(12) C13 0.0396(11) 0.0476(12) 0.0851(16) 0.0174(12) 0.0017(12) 0.0072(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10A 1.431(2) . ? O1 C2 1.464(2) . ? C2 O3 1.460(2) . ? C2 C13 1.508(3) . ? C2 C12 1.516(3) . ? O3 C3A 1.439(2) . ? C3A C4 1.507(3) . ? C3A C10A 1.511(2) . ? C3A H3A 0.9800 . ? C4 N5 1.482(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N5 C6 1.494(2) . ? N5 C9A 1.509(2) . ? C6 C7 1.526(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.520(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.534(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C9A 1.539(2) . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C9A C10 1.579(2) . ? C9A H9A 0.9800 . ? C10 O2 1.4349(19) . ? C10 C10A 1.519(2) . ? C10 C11 1.541(2) . ? C10A H10A 0.9800 . ? O2 H2 0.8200 . ? O4 C11 1.425(2) . ? O4 H4 0.8200 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10A O1 C2 106.21(13) . . ? O3 C2 O1 105.90(13) . . ? O3 C2 C13 107.55(16) . . ? O1 C2 C13 110.27(16) . . ? O3 C2 C12 110.80(16) . . ? O1 C2 C12 107.90(16) . . ? C13 C2 C12 114.11(18) . . ? C3A O3 C2 105.58(13) . . ? O3 C3A C4 115.12(15) . . ? O3 C3A C10A 100.96(13) . . ? C4 C3A C10A 108.81(15) . . ? O3 C3A H3A 110.5 . . ? C4 C3A H3A 110.5 . . ? C10A C3A H3A 110.5 . . ? N5 C4 C3A 107.19(14) . . ? N5 C4 H4A 110.3 . . ? C3A C4 H4A 110.3 . . ? N5 C4 H4B 110.3 . . ? C3A C4 H4B 110.3 . . ? H4A C4 H4B 108.5 . . ? C4 N5 C6 107.76(13) . . ? C4 N5 C9A 113.11(13) . . ? C6 N5 C9A 109.26(13) . . ? N5 C6 C7 112.46(15) . . ? N5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? N5 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 110.96(17) . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C7 C8 C9 109.60(16) . . ? C7 C8 H8A 109.8 . . ? C9 C8 H8A 109.8 . . ? C7 C8 H8B 109.8 . . ? C9 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C8 C9 C9A 111.06(15) . . ? C8 C9 H9B 109.4 . . ? C9A C9 H9B 109.4 . . ? C8 C9 H9C 109.4 . . ? C9A C9 H9C 109.4 . . ? H9B C9 H9C 108.0 . . ? N5 C9A C9 109.35(14) . . ? N5 C9A C10 114.53(13) . . ? C9 C9A C10 112.07(14) . . ? N5 C9A H9A 106.8 . . ? C9 C9A H9A 106.8 . . ? C10 C9A H9A 106.8 . . ? O2 C10 C10A 110.96(13) . . ? O2 C10 C11 105.63(13) . . ? C10A C10 C11 112.29(14) . . ? O2 C10 C9A 108.44(13) . . ? C10A C10 C9A 104.31(13) . . ? C11 C10 C9A 115.25(13) . . ? O1 C10A C3A 102.38(14) . . ? O1 C10A C10 117.98(14) . . ? C3A C10A C10 112.71(14) . . ? O1 C10A H10A 107.8 . . ? C3A C10A H10A 107.8 . . ? C10 C10A H10A 107.8 . . ? C10 O2 H2 109.5 . . ? C11 O4 H4 109.5 . . ? O4 C11 C10 111.78(14) . . ? O4 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? O4 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C2 C12 H12A 109.5 . . ? C2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10A O1 C2 O3 9.55(18) . . . . ? C10A O1 C2 C13 -106.52(18) . . . . ? C10A O1 C2 C12 128.24(17) . . . . ? O1 C2 O3 C3A 18.58(18) . . . . ? C13 C2 O3 C3A 136.48(16) . . . . ? C12 C2 O3 C3A -98.17(17) . . . . ? C2 O3 C3A C4 -154.60(15) . . . . ? C2 O3 C3A C10A -37.64(17) . . . . ? O3 C3A C4 N5 175.25(13) . . . . ? C10A C3A C4 N5 62.82(18) . . . . ? C3A C4 N5 C6 -178.09(14) . . . . ? C3A C4 N5 C9A -57.21(18) . . . . ? C4 N5 C6 C7 -177.82(15) . . . . ? C9A N5 C6 C7 58.9(2) . . . . ? N5 C6 C7 C8 -56.4(2) . . . . ? C6 C7 C8 C9 53.7(2) . . . . ? C7 C8 C9 C9A -56.4(2) . . . . ? C4 N5 C9A C9 -179.72(14) . . . . ? C6 N5 C9A C9 -59.70(17) . . . . ? C4 N5 C9A C10 53.55(18) . . . . ? C6 N5 C9A C10 173.57(14) . . . . ? C8 C9 C9A N5 59.69(19) . . . . ? C8 C9 C9A C10 -172.20(14) . . . . ? N5 C9A C10 O2 -168.37(12) . . . . ? C9 C9A C10 O2 66.32(17) . . . . ? N5 C9A C10 C10A -50.06(17) . . . . ? C9 C9A C10 C10A -175.38(14) . . . . ? N5 C9A C10 C11 73.51(17) . . . . ? C9 C9A C10 C11 -51.80(19) . . . . ? C2 O1 C10A C3A -32.37(17) . . . . ? C2 O1 C10A C10 -156.73(15) . . . . ? O3 C3A C10A O1 43.29(16) . . . . ? C4 C3A C10A O1 164.81(13) . . . . ? O3 C3A C10A C10 171.07(14) . . . . ? C4 C3A C10A C10 -67.41(19) . . . . ? O2 C10 C10A O1 -67.2(2) . . . . ? C11 C10 C10A O1 50.8(2) . . . . ? C9A C10 C10A O1 176.25(14) . . . . ? O2 C10 C10A C3A 173.76(14) . . . . ? C11 C10 C10A C3A -68.28(19) . . . . ? C9A C10 C10A C3A 57.20(18) . . . . ? O2 C10 C11 O4 -36.13(18) . . . . ? C10A C10 C11 O4 -157.21(14) . . . . ? C9A C10 C11 O4 83.54(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.153 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.052