# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 ####################################################################### # # 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_fpbr-1 _database_code_depnum_ccdc_archive 'CCDC 765895' #TrackingRef 'FPBR-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 Br O' _chemical_formula_sum 'C17 H21 Br O' _chemical_formula_weight 321.24 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.7575(2) _cell_length_b 9.8672(4) _cell_length_c 16.6178(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.210(2) _cell_angle_gamma 90.00 _cell_volume 779.51(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2848 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 21.50 _exptl_crystal_description Flake _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 331.55 _exptl_absorpt_coefficient_mu 5.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.144 _exptl_absorpt_correction_T_max 0.273 _exptl_absorpt_process_details multi-scan _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_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5238 _diffrn_reflns_av_R_equivalents 0.1081 _diffrn_reflns_av_sigmaI/netI 0.0717 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 21.60 _reflns_number_total 1797 _reflns_number_gt 963 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.1000P)^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 constr _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 -0.04(2) _refine_ls_number_reflns 1797 _refine_ls_number_parameters 174 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1449 _refine_ls_wR_factor_gt 0.1308 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 Br1 Br 0.42959(16) 1.03756(12) -0.18834(4) 0.0794(4) Uani 1 1 d . . . C1 C 0.6123(12) 1.0416(11) -0.0853(4) 0.0495(16) Uani 1 1 d . . . C4 C 0.8830(11) 1.0452(10) 0.0654(3) 0.0407(15) Uani 1 1 d . . . C6 C 0.8103(16) 1.1407(8) -0.0678(4) 0.055(2) Uani 1 1 d . . . H6 H 0.8532 1.2057 -0.1059 0.066 Uiso 1 1 calc R . . C5 C 0.9426(16) 1.1415(8) 0.0070(5) 0.054(2) Uani 1 1 d . . . H5 H 1.0759 1.2080 0.0192 0.064 Uiso 1 1 calc R . . C3 C 0.6829(15) 0.9484(8) 0.0469(4) 0.0474(18) Uani 1 1 d . . . H3 H 0.6381 0.8840 0.0852 0.057 Uiso 1 1 calc R . . C2 C 0.5481(16) 0.9462(8) -0.0282(5) 0.054(2) Uani 1 1 d . . . H2 H 0.4137 0.8802 -0.0403 0.064 Uiso 1 1 calc R . . C10 C 1.1852(13) 1.0415(12) 0.3104(4) 0.0501(16) Uani 1 1 d . . . C8 C 0.9216(19) 1.1640(9) 0.2000(5) 0.053(2) Uani 1 1 d . . . H8A H 0.7192 1.1545 0.2027 0.064 Uiso 1 1 calc R . . H8B H 0.9602 1.2519 0.1768 0.064 Uiso 1 1 calc R . . C7 C 1.0339(13) 1.0540(9) 0.1465(4) 0.0435(17) Uani 1 1 d . . . H7 H 1.2334 1.0718 0.1383 0.052 Uiso 1 1 calc R . . C9 C 1.0547(17) 1.1568(9) 0.2848(4) 0.053(2) Uani 1 1 d . . . C11 C 1.3432(15) 1.0256(12) 0.3888(4) 0.065(2) Uani 1 1 d . . . H11A H 1.3186 1.1062 0.4212 0.078 Uiso 1 1 calc R . . H11B H 1.5422 1.0161 0.3793 0.078 Uiso 1 1 calc R . . C15 C 1.1869(15) 0.9187(8) 0.2585(4) 0.0460(19) Uani 1 1 d . . . H15 H 1.3802 0.9017 0.2428 0.055 Uiso 1 1 calc R . . C12 C 1.2410(18) 0.9008(8) 0.4350(4) 0.066(2) Uani 1 1 d . . . H12A H 1.3581 0.8889 0.4835 0.079 Uiso 1 1 calc R . . H12B H 1.0495 0.9161 0.4508 0.079 Uiso 1 1 calc R . . C14 C 1.0856(18) 0.7963(9) 0.3056(4) 0.048(2) Uani 1 1 d . . . H14A H 0.8886 0.8087 0.3168 0.057 Uiso 1 1 calc R . . H14B H 1.1007 0.7158 0.2725 0.057 Uiso 1 1 calc R . . C13 C 1.2513(14) 0.7740(8) 0.3848(4) 0.051(2) Uani 1 1 d . . . H13 H 1.4479 0.7570 0.3724 0.062 Uiso 1 1 calc R . . C16 C 1.033(3) 1.2833(11) 0.3344(7) 0.096(4) Uani 1 1 d . . . H16A H 0.8393 1.3007 0.3447 0.144 Uiso 1 1 calc R . . H16B H 1.1092 1.3584 0.3057 0.144 Uiso 1 1 calc R . . H16C H 1.1372 1.2716 0.3846 0.144 Uiso 1 1 calc R . . O1 O 1.0102(12) 0.9279(6) 0.1874(3) 0.0478(15) Uani 1 1 d . . . C17 C 1.141(2) 0.6506(10) 0.4277(5) 0.077(3) Uani 1 1 d . . . H17A H 1.2280 0.6451 0.4807 0.115 Uiso 1 1 calc R . . H17B H 1.1855 0.5705 0.3978 0.115 Uiso 1 1 calc R . . H17C H 0.9412 0.6578 0.4316 0.115 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 Br1 0.0887(6) 0.0923(7) 0.0557(6) 0.0094(6) -0.0190(4) -0.0093(7) C1 0.047(3) 0.040(4) 0.062(4) -0.007(6) -0.005(3) 0.003(5) C4 0.045(3) 0.040(4) 0.036(3) -0.009(5) 0.003(3) -0.002(5) C6 0.063(5) 0.053(5) 0.048(5) 0.004(4) -0.003(4) 0.007(4) C5 0.056(4) 0.044(5) 0.060(5) 0.002(4) -0.006(4) -0.014(4) C3 0.059(4) 0.043(5) 0.040(5) 0.006(4) 0.001(4) 0.000(4) C2 0.061(5) 0.043(5) 0.056(5) 0.005(4) 0.000(4) -0.009(4) C10 0.052(3) 0.049(5) 0.049(4) 0.013(6) -0.001(3) -0.011(6) C8 0.063(5) 0.037(5) 0.058(6) -0.002(4) -0.007(4) 0.001(4) C7 0.049(3) 0.041(5) 0.041(4) -0.007(5) 0.002(3) -0.004(4) C9 0.061(5) 0.055(6) 0.042(5) -0.008(4) 0.002(4) -0.005(5) C11 0.071(4) 0.065(6) 0.057(4) -0.010(6) -0.015(3) 0.001(6) C15 0.039(4) 0.049(5) 0.051(5) -0.001(4) -0.002(4) 0.006(4) C12 0.081(6) 0.074(6) 0.040(5) 0.004(5) -0.016(4) -0.002(5) C14 0.056(4) 0.045(5) 0.040(4) 0.002(4) -0.010(3) 0.010(4) C13 0.049(4) 0.054(5) 0.051(5) 0.007(4) -0.004(4) 0.007(4) C16 0.158(10) 0.042(6) 0.086(7) -0.014(6) -0.020(8) 0.012(7) O1 0.061(3) 0.040(3) 0.042(4) 0.000(2) -0.008(3) 0.003(2) C17 0.105(7) 0.067(6) 0.057(5) 0.009(5) -0.013(5) 0.001(5) _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 Br1 C1 1.891(6) . ? C1 C2 1.379(11) . ? C1 C6 1.381(12) . ? C4 C3 1.375(11) . ? C4 C5 1.394(11) . ? C4 C7 1.505(9) . ? C6 C5 1.371(11) . ? C3 C2 1.380(10) . ? C10 C9 1.357(14) . ? C10 C11 1.487(9) . ? C10 C15 1.488(14) . ? C8 C7 1.514(11) . ? C8 C9 1.523(11) . ? C7 O1 1.425(11) . ? C9 C16 1.502(14) . ? C11 C12 1.539(13) . ? C15 O1 1.427(9) . ? C15 C14 1.528(11) . ? C12 C13 1.505(11) . ? C14 C13 1.523(10) . ? C13 C17 1.514(11) . ? 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 C2 C1 C6 120.4(6) . . ? C2 C1 Br1 120.2(6) . . ? C6 C1 Br1 119.4(7) . . ? C3 C4 C5 118.4(6) . . ? C3 C4 C7 122.8(7) . . ? C5 C4 C7 118.8(7) . . ? C5 C6 C1 118.7(7) . . ? C6 C5 C4 121.9(7) . . ? C4 C3 C2 120.4(7) . . ? C1 C2 C3 120.2(7) . . ? C9 C10 C11 125.0(10) . . ? C9 C10 C15 120.9(6) . . ? C11 C10 C15 114.1(9) . . ? C7 C8 C9 111.5(7) . . ? O1 C7 C4 109.5(7) . . ? O1 C7 C8 108.0(5) . . ? C4 C7 C8 113.6(7) . . ? C10 C9 C16 124.3(8) . . ? C10 C9 C8 119.9(7) . . ? C16 C9 C8 115.7(8) . . ? C10 C11 C12 111.2(8) . . ? O1 C15 C10 114.3(6) . . ? O1 C15 C14 106.7(6) . . ? C10 C15 C14 109.8(6) . . ? C13 C12 C11 111.8(6) . . ? C13 C14 C15 113.2(7) . . ? C12 C13 C17 112.9(6) . . ? C12 C13 C14 109.4(6) . . ? C17 C13 C14 110.2(7) . . ? C7 O1 C15 113.3(6) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 21.60 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.463 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.115 data_ss-le _database_code_depnum_ccdc_archive 'CCDC 765896' #TrackingRef 'SS-Le.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H20 O4 S' _chemical_formula_sum 'C19 H20 O4 S' _chemical_formula_weight 344.41 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8247(5) _cell_length_b 11.1954(6) _cell_length_c 16.1562(9) _cell_angle_alpha 101.883(3) _cell_angle_beta 95.733(3) _cell_angle_gamma 91.650(3) _cell_volume 1728.04(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6956 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.97 _exptl_crystal_description Rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.207 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9219 _exptl_absorpt_correction_T_max 0.9501 _exptl_absorpt_process_details multi-scan _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_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18086 _diffrn_reflns_av_R_equivalents 0.1139 _diffrn_reflns_av_sigmaI/netI 0.0826 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 29.66 _reflns_number_total 9793 _reflns_number_gt 5131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0770P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8244 _refine_ls_number_parameters 437 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1578 _refine_ls_wR_factor_gt 0.1409 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.001 _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 S2 S 0.28461(5) 0.62319(4) 0.11906(3) 0.04944(15) Uani 1 1 d . . . S1 S 0.94062(5) 0.88095(5) 0.87060(3) 0.05230(16) Uani 1 1 d . . . C32 C 0.10569(19) 0.61406(16) 0.11421(10) 0.0433(4) Uani 1 1 d . . . C37 C 0.0368(2) 0.50710(18) 0.11908(12) 0.0522(5) Uani 1 1 d . . . H37 H 0.0852 0.4394 0.1270 0.063 Uiso 1 1 calc R . . C35 C -0.1784(2) 0.6018(2) 0.10253(11) 0.0558(5) Uani 1 1 d . . . C33 C 0.0335(2) 0.71420(18) 0.10186(13) 0.0547(5) Uani 1 1 d . . . H33 H 0.0797 0.7855 0.0967 0.066 Uiso 1 1 calc R . . C36 C -0.1040(2) 0.5012(2) 0.11217(12) 0.0581(5) Uani 1 1 d . . . H36 H -0.1502 0.4283 0.1140 0.070 Uiso 1 1 calc R . . C34 C -0.1072(2) 0.7075(2) 0.09730(13) 0.0597(5) Uani 1 1 d . . . H34 H -0.1554 0.7758 0.0906 0.072 Uiso 1 1 calc R . . C38 C -0.3322(2) 0.5960(3) 0.09895(15) 0.0811(7) Uani 1 1 d . . . H38A H -0.3670 0.5139 0.0750 0.122 Uiso 1 1 calc R . . H38B H -0.3693 0.6498 0.0641 0.122 Uiso 1 1 calc R . . H38C H -0.3584 0.6208 0.1554 0.122 Uiso 1 1 calc R . . O15 O 0.32680(15) 0.67712(14) 0.05318(9) 0.0658(4) Uani 1 1 d . . . O13 O 0.33210(14) 0.72702(11) 0.20236(8) 0.0530(3) Uani 1 1 d . . . C29 C 0.3174(2) 0.70553(17) 0.28415(12) 0.0501(5) Uani 1 1 d . . . C30 C 0.2177(2) 0.76455(19) 0.32788(13) 0.0598(5) Uani 1 1 d . . . H30 H 0.1563 0.8106 0.3017 0.072 Uiso 1 1 calc R . . C26 C 0.2989(2) 0.6880(2) 0.45108(13) 0.0594(5) Uani 1 1 d . . . C27 C 0.3974(2) 0.6281(2) 0.40550(14) 0.0682(6) Uani 1 1 d . . . H27 H 0.4573 0.5802 0.4310 0.082 Uiso 1 1 calc R . . C28 C 0.4087(2) 0.6383(2) 0.32156(13) 0.0637(6) Uani 1 1 d . . . H28 H 0.4773 0.5999 0.2919 0.076 Uiso 1 1 calc R . . C31 C 0.2090(2) 0.7552(2) 0.41109(14) 0.0652(6) Uani 1 1 d . . . H31 H 0.1411 0.7951 0.4406 0.078 Uiso 1 1 calc R . . C24 C 0.2841(2) 0.6793(2) 0.54226(13) 0.0660(6) Uani 1 1 d . . . H24 H 0.2561 0.7584 0.5724 0.079 Uiso 1 1 calc R . . C22 C 0.1812(2) 0.55757(18) 0.63616(13) 0.0584(5) Uani 1 1 d . . . C23 C 0.1770(2) 0.58227(19) 0.54827(12) 0.0589(5) Uani 1 1 d . . . H23A H 0.0869 0.6086 0.5318 0.071 Uiso 1 1 calc R . . H23B H 0.1918 0.5072 0.5087 0.071 Uiso 1 1 calc R . . C25 C 0.0624(3) 0.4868(2) 0.65452(15) 0.0758(7) Uani 1 1 d . . . H25A H 0.0794 0.4707 0.7106 0.114 Uiso 1 1 calc R . . H25B H 0.0486 0.4109 0.6136 0.114 Uiso 1 1 calc R . . H25C H -0.0181 0.5331 0.6512 0.114 Uiso 1 1 calc R . . C20 C 0.4088(3) 0.6649(3) 0.67061(14) 0.0889(8) Uani 1 1 d . . . H20A H 0.4077 0.7502 0.6984 0.107 Uiso 1 1 calc R . . H20B H 0.4920 0.6327 0.6931 0.107 Uiso 1 1 calc R . . C21 C 0.2900(3) 0.5982(2) 0.69121(14) 0.0765(7) Uani 1 1 d . . . H21 H 0.2913 0.5837 0.7459 0.092 Uiso 1 1 calc R . . O12 O 0.41155(17) 0.65649(18) 0.58156(10) 0.0883(6) Uani 1 1 d . . . C13 C 0.76382(19) 0.88569(17) 0.87877(11) 0.0468(4) Uani 1 1 d . . . C16 C 0.4849(2) 0.8922(2) 0.89472(12) 0.0581(5) Uani 1 1 d . . . C10 C 0.9055(2) 0.78978(18) 0.70753(12) 0.0514(5) Uani 1 1 d . . . C14 C 0.6957(2) 0.98754(19) 0.86837(13) 0.0586(5) Uani 1 1 d . . . H14 H 0.7417 1.0539 0.8553 0.070 Uiso 1 1 calc R . . C18 C 0.6950(2) 0.78702(19) 0.89773(14) 0.0631(6) Uani 1 1 d . . . H18 H 0.7416 0.7184 0.9055 0.076 Uiso 1 1 calc R . . C9 C 0.7863(2) 0.7300(2) 0.66808(14) 0.0637(6) Uani 1 1 d . . . H9 H 0.7341 0.6841 0.6964 0.076 Uiso 1 1 calc R . . C4 C 0.6631(2) 0.9120(2) 0.45079(13) 0.0623(5) Uani 1 1 d . . . H4A H 0.5791 0.8835 0.4689 0.075 Uiso 1 1 calc R . . H4B H 0.6962 0.9869 0.4905 0.075 Uiso 1 1 calc R . . C15 C 0.5572(2) 0.9898(2) 0.87762(14) 0.0663(6) Uani 1 1 d . . . H15 H 0.5114 1.0598 0.8721 0.080 Uiso 1 1 calc R . . C3 C 0.6335(2) 0.9383(2) 0.36389(14) 0.0628(5) Uani 1 1 d . . . C7 C 0.8203(2) 0.8062(2) 0.54254(13) 0.0598(5) Uani 1 1 d . . . C11 C 0.9853(2) 0.8560(2) 0.66717(13) 0.0641(6) Uani 1 1 d . . . H11 H 1.0680 0.8939 0.6943 0.077 Uiso 1 1 calc R . . C5 C 0.7693(2) 0.8162(2) 0.45300(13) 0.0646(6) Uani 1 1 d . . . H5 H 0.7268 0.7368 0.4230 0.078 Uiso 1 1 calc R . . C8 C 0.7437(2) 0.7385(2) 0.58506(14) 0.0686(6) Uani 1 1 d . . . H8 H 0.6624 0.6981 0.5578 0.082 Uiso 1 1 calc R . . C12 C 0.9399(3) 0.8658(2) 0.58386(13) 0.0685(6) Uani 1 1 d . . . H12 H 0.9915 0.9132 0.5562 0.082 Uiso 1 1 calc R . . C2 C 0.7166(3) 0.8992(2) 0.30542(14) 0.0770(7) Uani 1 1 d . . . H2 H 0.6949 0.9134 0.2510 0.092 Uiso 1 1 calc R . . C17 C 0.5568(2) 0.7912(2) 0.90493(15) 0.0693(6) Uani 1 1 d . . . H17 H 0.5106 0.7242 0.9170 0.083 Uiso 1 1 calc R . . C19 C 0.3338(2) 0.8935(3) 0.90056(16) 0.0862(8) Uani 1 1 d . . . H19A H 0.3091 0.9757 0.9215 0.129 Uiso 1 1 calc R . . H19B H 0.3097 0.8430 0.9387 0.129 Uiso 1 1 calc R . . H19C H 0.2857 0.8627 0.8452 0.129 Uiso 1 1 calc R . . C1 C 0.8414(3) 0.8344(3) 0.32210(14) 0.0883(8) Uani 1 1 d . . . H1A H 0.8259 0.7489 0.2944 0.106 Uiso 1 1 calc R . . H1B H 0.9156 0.8679 0.2971 0.106 Uiso 1 1 calc R . . O4 O 0.88180(17) 0.84283(17) 0.41052(9) 0.0823(5) Uani 1 1 d . . . O9 O 0.95155(14) 0.77212(11) 0.78988(8) 0.0552(3) Uani 1 1 d . . . O11 O 1.00680(16) 0.83400(16) 0.93792(9) 0.0740(5) Uani 1 1 d . . . O14 O 0.33573(14) 0.51059(12) 0.13146(9) 0.0631(4) Uani 1 1 d . . . O10 O 0.98864(15) 0.99155(12) 0.85152(9) 0.0639(4) Uani 1 1 d . . . C6 C 0.5095(3) 1.0074(2) 0.34951(16) 0.0802(7) Uani 1 1 d . . . H6A H 0.5034 1.0238 0.2933 0.120 Uiso 1 1 calc R . . H6B H 0.5155 1.0832 0.3906 0.120 Uiso 1 1 calc R . . H6C H 0.4295 0.9599 0.3554 0.120 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 S2 0.0401(3) 0.0542(3) 0.0556(3) 0.0138(2) 0.0084(2) 0.0008(2) S1 0.0419(3) 0.0610(3) 0.0550(3) 0.0136(2) 0.0070(2) 0.0035(2) C32 0.0394(10) 0.0499(10) 0.0409(9) 0.0104(8) 0.0051(8) 0.0005(8) C37 0.0470(11) 0.0524(10) 0.0613(11) 0.0191(9) 0.0104(9) 0.0029(9) C35 0.0395(11) 0.0828(14) 0.0421(9) 0.0068(10) 0.0038(8) 0.0013(10) C33 0.0501(12) 0.0510(10) 0.0643(12) 0.0180(10) 0.0017(10) 0.0003(9) C36 0.0495(12) 0.0654(12) 0.0610(12) 0.0161(10) 0.0114(10) -0.0084(10) C34 0.0497(12) 0.0632(12) 0.0650(12) 0.0125(11) 0.0000(10) 0.0122(10) C38 0.0453(13) 0.118(2) 0.0757(15) 0.0101(15) 0.0094(11) 0.0031(13) O15 0.0536(9) 0.0884(10) 0.0615(8) 0.0258(8) 0.0173(7) -0.0053(8) O13 0.0500(8) 0.0534(7) 0.0559(7) 0.0157(6) 0.0016(6) -0.0087(6) C29 0.0446(11) 0.0531(10) 0.0521(10) 0.0134(9) 0.0006(9) -0.0095(9) C30 0.0457(12) 0.0667(13) 0.0669(13) 0.0159(11) 0.0020(10) 0.0009(10) C26 0.0497(13) 0.0712(13) 0.0546(11) 0.0110(11) 0.0022(10) -0.0144(10) C27 0.0585(14) 0.0866(15) 0.0618(12) 0.0244(12) -0.0021(11) 0.0079(12) C28 0.0524(13) 0.0786(14) 0.0618(12) 0.0171(11) 0.0071(10) 0.0109(11) C31 0.0520(13) 0.0779(14) 0.0652(13) 0.0113(12) 0.0129(11) -0.0005(11) C24 0.0568(14) 0.0826(15) 0.0564(12) 0.0124(12) 0.0040(11) -0.0081(12) C22 0.0623(14) 0.0576(12) 0.0539(11) 0.0088(10) 0.0065(10) 0.0011(10) C23 0.0539(13) 0.0662(12) 0.0540(11) 0.0105(10) 0.0005(10) -0.0052(10) C25 0.0822(18) 0.0807(15) 0.0673(14) 0.0236(13) 0.0074(13) -0.0076(13) C20 0.0756(19) 0.128(2) 0.0563(13) 0.0169(15) -0.0103(12) -0.0241(17) C21 0.0792(18) 0.0975(18) 0.0531(12) 0.0201(13) 0.0035(12) -0.0088(15) O12 0.0547(10) 0.1479(16) 0.0594(9) 0.0241(10) -0.0057(8) -0.0217(10) C13 0.0405(10) 0.0524(10) 0.0489(10) 0.0133(9) 0.0060(8) 0.0031(8) C16 0.0405(11) 0.0815(14) 0.0500(11) 0.0096(11) 0.0031(9) 0.0030(10) C10 0.0453(11) 0.0542(11) 0.0555(11) 0.0094(9) 0.0111(9) 0.0091(9) C14 0.0497(12) 0.0577(11) 0.0722(13) 0.0229(11) 0.0047(10) 0.0043(9) C18 0.0522(13) 0.0565(11) 0.0883(15) 0.0287(11) 0.0152(11) 0.0072(10) C9 0.0562(14) 0.0666(13) 0.0694(13) 0.0159(11) 0.0112(11) -0.0037(11) C4 0.0596(13) 0.0670(13) 0.0582(12) 0.0053(11) 0.0125(10) 0.0028(11) C15 0.0507(13) 0.0721(14) 0.0774(14) 0.0187(12) 0.0019(11) 0.0196(11) C3 0.0622(14) 0.0621(12) 0.0611(12) 0.0069(11) 0.0053(11) 0.0005(11) C7 0.0528(13) 0.0670(13) 0.0570(11) 0.0040(10) 0.0113(10) 0.0080(10) C11 0.0511(13) 0.0797(14) 0.0599(12) 0.0112(11) 0.0093(10) -0.0085(11) C5 0.0577(14) 0.0765(14) 0.0572(12) 0.0076(11) 0.0081(10) 0.0027(11) C8 0.0530(14) 0.0775(15) 0.0710(14) 0.0096(12) 0.0009(11) -0.0044(11) C12 0.0623(15) 0.0849(15) 0.0584(12) 0.0134(12) 0.0150(11) -0.0092(12) C2 0.0800(18) 0.0968(18) 0.0533(12) 0.0136(13) 0.0064(12) 0.0100(15) C17 0.0526(14) 0.0764(15) 0.0854(16) 0.0310(13) 0.0129(12) -0.0066(11) C19 0.0450(14) 0.137(2) 0.0755(15) 0.0202(16) 0.0071(12) 0.0092(15) C1 0.088(2) 0.122(2) 0.0543(13) 0.0112(14) 0.0178(13) 0.0221(17) O4 0.0658(11) 0.1259(14) 0.0560(8) 0.0138(9) 0.0168(8) 0.0190(10) O9 0.0543(8) 0.0539(7) 0.0594(8) 0.0128(7) 0.0102(7) 0.0142(6) O11 0.0523(9) 0.1129(13) 0.0625(9) 0.0335(9) -0.0012(7) 0.0149(9) O14 0.0478(8) 0.0569(8) 0.0840(10) 0.0130(8) 0.0063(7) 0.0081(7) O10 0.0555(9) 0.0614(8) 0.0733(9) 0.0084(7) 0.0145(7) -0.0066(7) C6 0.0803(18) 0.0866(17) 0.0761(15) 0.0205(14) 0.0101(13) 0.0111(14) _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 S2 O14 1.4148(14) . ? S2 O15 1.4169(14) . ? S2 O13 1.6060(13) . ? S2 C32 1.7508(19) . ? S1 O11 1.4128(15) . ? S1 O10 1.4154(14) . ? S1 O9 1.6057(13) . ? S1 C13 1.7566(19) . ? C32 C37 1.379(3) . ? C32 C33 1.382(3) . ? C37 C36 1.375(3) . ? C35 C34 1.379(3) . ? C35 C36 1.387(3) . ? C35 C38 1.506(3) . ? C33 C34 1.377(3) . ? O13 C29 1.411(2) . ? C29 C28 1.362(3) . ? C29 C30 1.371(3) . ? C30 C31 1.380(3) . ? C26 C31 1.375(3) . ? C26 C27 1.380(3) . ? C26 C24 1.517(3) . ? C27 C28 1.399(3) . ? C24 O12 1.401(3) . ? C24 C23 1.514(3) . ? C22 C21 1.325(3) . ? C22 C25 1.480(3) . ? C22 C23 1.498(3) . ? C20 O12 1.425(3) . ? C20 C21 1.470(4) . ? C13 C14 1.370(3) . ? C13 C18 1.382(3) . ? C16 C15 1.377(3) . ? C16 C17 1.380(3) . ? C16 C19 1.497(3) . ? C10 C9 1.362(3) . ? C10 C11 1.363(3) . ? C10 O9 1.417(2) . ? C14 C15 1.384(3) . ? C18 C17 1.375(3) . ? C9 C8 1.388(3) . ? C4 C3 1.495(3) . ? C4 C5 1.521(3) . ? C3 C2 1.324(3) . ? C3 C6 1.486(3) . ? C7 C12 1.373(3) . ? C7 C8 1.377(3) . ? C7 C5 1.510(3) . ? C11 C12 1.402(3) . ? C5 O4 1.414(3) . ? C2 C1 1.473(4) . ? C1 O4 1.427(3) . ? 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 O14 S2 O15 120.45(9) . . ? O14 S2 O13 108.92(8) . . ? O15 S2 O13 102.12(8) . . ? O14 S2 C32 109.06(9) . . ? O15 S2 C32 110.57(9) . . ? O13 S2 C32 104.35(8) . . ? O11 S1 O10 121.25(10) . . ? O11 S1 O9 102.19(9) . . ? O10 S1 O9 108.56(8) . . ? O11 S1 C13 110.23(9) . . ? O10 S1 C13 109.34(9) . . ? O9 S1 C13 103.63(8) . . ? C37 C32 C33 120.14(18) . . ? C37 C32 S2 120.74(14) . . ? C33 C32 S2 119.06(14) . . ? C36 C37 C32 119.53(18) . . ? C34 C35 C36 118.07(19) . . ? C34 C35 C38 121.1(2) . . ? C36 C35 C38 120.9(2) . . ? C34 C33 C32 119.47(19) . . ? C37 C36 C35 121.3(2) . . ? C33 C34 C35 121.42(19) . . ? C29 O13 S2 120.41(11) . . ? C28 C29 C30 121.12(19) . . ? C28 C29 O13 120.58(18) . . ? C30 C29 O13 117.96(18) . . ? C29 C30 C31 119.6(2) . . ? C31 C26 C27 118.30(19) . . ? C31 C26 C24 119.2(2) . . ? C27 C26 C24 122.5(2) . . ? C26 C27 C28 121.2(2) . . ? C29 C28 C27 118.7(2) . . ? C26 C31 C30 121.1(2) . . ? O12 C24 C23 110.56(19) . . ? O12 C24 C26 109.08(18) . . ? C23 C24 C26 112.57(18) . . ? C21 C22 C25 124.7(2) . . ? C21 C22 C23 118.6(2) . . ? C25 C22 C23 116.69(19) . . ? C22 C23 C24 112.26(17) . . ? O12 C20 C21 113.2(2) . . ? C22 C21 C20 123.7(2) . . ? C24 O12 C20 111.67(19) . . ? C14 C13 C18 120.41(19) . . ? C14 C13 S1 120.17(15) . . ? C18 C13 S1 119.40(15) . . ? C15 C16 C17 117.35(19) . . ? C15 C16 C19 121.8(2) . . ? C17 C16 C19 120.8(2) . . ? C9 C10 C11 121.8(2) . . ? C9 C10 O9 117.85(18) . . ? C11 C10 O9 120.14(19) . . ? C13 C14 C15 118.8(2) . . ? C17 C18 C13 119.4(2) . . ? C10 C9 C8 119.1(2) . . ? C3 C4 C5 112.00(16) . . ? C16 C15 C14 122.3(2) . . ? C2 C3 C6 124.4(2) . . ? C2 C3 C4 119.2(2) . . ? C6 C3 C4 116.31(18) . . ? C12 C7 C8 118.8(2) . . ? C12 C7 C5 121.6(2) . . ? C8 C7 C5 119.5(2) . . ? C10 C11 C12 118.6(2) . . ? O4 C5 C7 109.21(18) . . ? O4 C5 C4 110.34(18) . . ? C7 C5 C4 112.57(16) . . ? C7 C8 C9 120.9(2) . . ? C7 C12 C11 120.8(2) . . ? C3 C2 C1 123.4(2) . . ? C18 C17 C16 121.7(2) . . ? O4 C1 C2 113.29(19) . . ? C5 O4 C1 111.05(19) . . ? C10 O9 S1 119.02(11) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 29.66 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.343 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.056 data_somu-231 _database_code_depnum_ccdc_archive 'CCDC 801332' #TrackingRef 'AKS-amidoTHP.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H20 N2 O4' _chemical_formula_sum 'C19 H20 N2 O4' _chemical_formula_weight 340.37 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.6207(12) _cell_length_b 19.274(2) _cell_length_c 16.3163(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.451(7) _cell_angle_gamma 90.00 _cell_volume 3593.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1395 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 13.12 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details multi-scan _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_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17415 _diffrn_reflns_av_R_equivalents 0.0857 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.77 _reflns_number_total 8475 _reflns_number_gt 6487 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0768P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8475 _refine_ls_number_parameters 453 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0988 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1411 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 C1 C -0.0283(6) 0.3607(4) 0.9258(4) 0.078(2) Uani 1 1 d . . . H1A H -0.0528 0.3259 0.9620 0.093 Uiso 1 1 calc R . . H1B H 0.0543 0.3697 0.9453 0.093 Uiso 1 1 calc R . . C2 C -0.0453(5) 0.3327(3) 0.8384(5) 0.072(2) Uani 1 1 d . . . H2A H -0.1267 0.3199 0.8204 0.087 Uiso 1 1 calc R . . H2B H 0.0019 0.2913 0.8376 0.087 Uiso 1 1 calc R . . C3 C -0.0110(7) 0.3860(3) 0.7777(4) 0.0574(17) Uani 1 1 d . . . C4 C -0.0778(5) 0.4531(3) 0.7900(4) 0.0607(18) Uani 1 1 d . . . H4A H -0.0519 0.4898 0.7569 0.073 Uiso 1 1 calc R . . H4B H -0.1607 0.4458 0.7698 0.073 Uiso 1 1 calc R . . C5 C -0.0593(5) 0.4759(4) 0.8808(4) 0.0565(18) Uani 1 1 d . . . H5 H 0.0240 0.4858 0.8995 0.068 Uiso 1 1 calc R . . C6 C -0.1279(7) 0.5403(5) 0.8928(5) 0.0541(18) Uani 1 1 d . . . C7 C -0.2173(8) 0.5425(4) 0.9382(4) 0.068(2) Uani 1 1 d . . . H7 H -0.2357 0.5030 0.9659 0.081 Uiso 1 1 calc R . . C8 C -0.2802(6) 0.6038(6) 0.9426(4) 0.075(2) Uani 1 1 d . . . H8 H -0.3421 0.6044 0.9717 0.090 Uiso 1 1 calc R . . C9 C -0.2512(8) 0.6629(4) 0.9044(5) 0.074(2) Uani 1 1 d . . . H9 H -0.2913 0.7042 0.9081 0.089 Uiso 1 1 calc R . . C10 C -0.1607(8) 0.6594(6) 0.8604(4) 0.067(2) Uani 1 1 d . . . C11 C -0.1004(6) 0.5995(6) 0.8534(4) 0.064(2) Uani 1 1 d . . . H11 H -0.0410 0.5988 0.8221 0.077 Uiso 1 1 calc R . . C12 C -0.0424(5) 0.3615(3) 0.6872(4) 0.087(2) Uani 1 1 d . . . H12A H -0.0239 0.3973 0.6508 0.131 Uiso 1 1 calc R . . H12B H -0.1246 0.3513 0.6740 0.131 Uiso 1 1 calc R . . H12C H 0.0015 0.3205 0.6800 0.131 Uiso 1 1 calc R . . C13 C 0.2040(8) 0.3567(5) 0.8047(3) 0.0571(19) Uani 1 1 d . . . C14 C 0.3234(8) 0.3886(5) 0.8160(4) 0.0529(18) Uani 1 1 d . . . C15 C 0.3503(9) 0.4540(6) 0.8473(4) 0.069(2) Uani 1 1 d . . . H15 H 0.2931 0.4805 0.8658 0.083 Uiso 1 1 calc R . . C16 C 0.4609(12) 0.4808(4) 0.8516(5) 0.087(2) Uani 1 1 d . . . H16 H 0.4785 0.5247 0.8741 0.105 Uiso 1 1 calc R . . C17 C 0.5455(7) 0.4428(6) 0.8228(5) 0.083(2) Uani 1 1 d . . . H17 H 0.6194 0.4617 0.8237 0.100 Uiso 1 1 calc R . . C18 C 0.5208(10) 0.3769(6) 0.7928(4) 0.084(2) Uani 1 1 d . . . H18 H 0.5782 0.3507 0.7744 0.100 Uiso 1 1 calc R . . C19 C 0.4111(11) 0.3500(4) 0.7901(4) 0.070(2) Uani 1 1 d . . . H19 H 0.3951 0.3051 0.7706 0.084 Uiso 1 1 calc R . . C20 C 0.3118(8) 0.6685(4) 0.5426(4) 0.093(2) Uani 1 1 d . . . H20A H 0.3366 0.7013 0.5041 0.111 Uiso 1 1 calc R . . H20B H 0.3602 0.6756 0.5970 0.111 Uiso 1 1 calc R . . C21 C 0.1848(7) 0.6820(3) 0.5480(4) 0.085(2) Uani 1 1 d . . . H21A H 0.1372 0.6779 0.4929 0.102 Uiso 1 1 calc R . . H21B H 0.1770 0.7290 0.5675 0.102 Uiso 1 1 calc R . . C22 C 0.1399(7) 0.6313(4) 0.6068(5) 0.0651(19) Uani 1 1 d . . . C23 C 0.1720(7) 0.5577(4) 0.5817(4) 0.077(2) Uani 1 1 d . . . H23A H 0.1565 0.5252 0.6238 0.092 Uiso 1 1 calc R . . H23B H 0.1216 0.5454 0.5296 0.092 Uiso 1 1 calc R . . C24 C 0.2964(8) 0.5500(4) 0.5716(5) 0.081(2) Uani 1 1 d . . . H24 H 0.3472 0.5559 0.6261 0.098 Uiso 1 1 calc R . . C25 C 0.3173(6) 0.4788(5) 0.5378(8) 0.088(2) Uani 1 1 d . . . C26 C 0.3191(9) 0.4214(8) 0.5870(6) 0.157(4) Uani 1 1 d . . . H26 H 0.3117 0.4274 0.6424 0.189 Uiso 1 1 calc R . . C27 C 0.3314(10) 0.3546(7) 0.5586(9) 0.179(5) Uani 1 1 d . . . H27 H 0.3296 0.3169 0.5939 0.214 Uiso 1 1 calc R . . C28 C 0.3460(8) 0.3447(5) 0.4790(10) 0.135(4) Uani 1 1 d . . . H28 H 0.3559 0.3006 0.4583 0.161 Uiso 1 1 calc R . . C29 C 0.3457(6) 0.4027(8) 0.4302(6) 0.092(3) Uani 1 1 d . . . C30 C 0.3305(6) 0.4690(5) 0.4572(8) 0.089(3) Uani 1 1 d . . . H30 H 0.3292 0.5066 0.4212 0.106 Uiso 1 1 calc R . . C31 C 0.0082(6) 0.6375(3) 0.6024(4) 0.096(2) Uani 1 1 d . . . H31A H -0.0166 0.6045 0.6398 0.144 Uiso 1 1 calc R . . H31B H -0.0313 0.6282 0.5465 0.144 Uiso 1 1 calc R . . H31C H -0.0105 0.6835 0.6182 0.144 Uiso 1 1 calc R . . C32 C 0.1961(6) 0.6121(4) 0.7622(5) 0.0543(19) Uani 1 1 d . . . C33 C 0.2684(8) 0.6393(4) 0.8400(5) 0.0498(17) Uani 1 1 d . . . C34 C 0.3700(9) 0.6769(4) 0.8408(5) 0.065(2) Uani 1 1 d . . . H34 H 0.3940 0.6874 0.7909 0.079 Uiso 1 1 calc R . . C35 C 0.4361(6) 0.6991(3) 0.9152(8) 0.078(2) Uani 1 1 d . . . H35 H 0.5042 0.7244 0.9149 0.093 Uiso 1 1 calc R . . C36 C 0.4017(9) 0.6840(4) 0.9901(5) 0.080(2) Uani 1 1 d . . . H36 H 0.4467 0.6982 1.0404 0.095 Uiso 1 1 calc R . . C37 C 0.2992(9) 0.6474(4) 0.9888(6) 0.079(2) Uani 1 1 d . . . H37 H 0.2737 0.6378 1.0385 0.094 Uiso 1 1 calc R . . C38 C 0.2359(6) 0.6255(3) 0.9158(7) 0.065(2) Uani 1 1 d . . . H38 H 0.1679 0.6002 0.9165 0.078 Uiso 1 1 calc R . . N1 N 0.1153(6) 0.4028(3) 0.7975(3) 0.0593(15) Uani 1 1 d . . . H1 H 0.1339 0.4459 0.8050 0.071 Uiso 1 1 calc R . . N2 N -0.1323(7) 0.7230(4) 0.8208(5) 0.108(2) Uani 1 1 d . . . N3 N 0.2011(4) 0.6475(2) 0.6919(4) 0.0579(15) Uani 1 1 d . . . H3 H 0.2451 0.6838 0.6972 0.069 Uiso 1 1 calc R . . N4 N 0.3629(7) 0.3932(4) 0.3433(6) 0.127(3) Uani 1 1 d . . . O1 O -0.0926(4) 0.4232(3) 0.9318(3) 0.0710(13) Uani 1 1 d . . . O2 O 0.1898(4) 0.2934(3) 0.8035(3) 0.0769(16) Uani 1 1 d . . . O3 O -0.1858(5) 0.7762(3) 0.8281(3) 0.118(2) Uani 1 1 d . . . O4 O -0.0513(7) 0.7213(3) 0.7843(4) 0.179(4) Uani 1 1 d . . . O5 O 0.3279(4) 0.5998(3) 0.5152(3) 0.0971(16) Uani 1 1 d . . . O6 O 0.1361(4) 0.5591(2) 0.7626(3) 0.0660(14) Uani 1 1 d . . . O7 O 0.3803(7) 0.3360(4) 0.3195(4) 0.180(3) Uani 1 1 d . . . O8 O 0.3546(7) 0.4417(4) 0.2980(4) 0.183(3) Uani 1 1 d . . . 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 0.099(6) 0.042(6) 0.097(7) 0.007(5) 0.032(5) -0.009(5) C2 0.080(5) 0.037(5) 0.104(6) -0.006(5) 0.024(5) -0.005(4) C3 0.069(6) 0.034(5) 0.071(6) -0.005(5) 0.018(4) -0.001(5) C4 0.065(5) 0.048(5) 0.071(6) -0.003(4) 0.018(4) -0.002(4) C5 0.075(5) 0.035(5) 0.063(6) 0.014(5) 0.022(4) -0.006(5) C6 0.071(6) 0.030(7) 0.061(5) 0.002(5) 0.012(5) 0.000(5) C7 0.071(6) 0.068(8) 0.071(5) 0.001(4) 0.032(5) -0.014(5) C8 0.062(5) 0.071(6) 0.099(6) -0.019(6) 0.032(4) 0.008(6) C9 0.081(7) 0.043(7) 0.100(6) -0.005(5) 0.019(5) -0.006(5) C10 0.073(6) 0.062(9) 0.076(6) -0.005(5) 0.046(5) -0.012(6) C11 0.071(5) 0.044(6) 0.085(5) -0.006(6) 0.038(4) 0.017(6) C12 0.097(6) 0.087(6) 0.076(5) -0.029(4) 0.012(4) -0.005(4) C13 0.066(7) 0.050(7) 0.057(5) 0.006(5) 0.017(4) 0.007(7) C14 0.063(7) 0.040(7) 0.060(5) -0.002(4) 0.023(5) 0.008(7) C15 0.065(8) 0.053(8) 0.088(5) -0.015(5) 0.012(4) 0.008(5) C16 0.076(7) 0.058(6) 0.123(7) -0.008(5) 0.006(6) -0.008(7) C17 0.071(7) 0.076(8) 0.104(6) 0.015(6) 0.019(5) -0.008(7) C18 0.085(9) 0.073(9) 0.097(6) -0.012(5) 0.026(5) 0.005(6) C19 0.084(7) 0.059(6) 0.066(5) -0.003(4) 0.014(5) 0.001(8) C20 0.152(9) 0.046(6) 0.087(6) 0.003(5) 0.041(5) -0.019(6) C21 0.128(8) 0.060(6) 0.064(5) 0.013(4) 0.008(5) 0.009(5) C22 0.091(7) 0.043(6) 0.058(6) 0.001(5) 0.004(5) 0.013(5) C23 0.110(7) 0.057(6) 0.065(5) 0.005(4) 0.021(5) -0.005(5) C24 0.121(8) 0.050(7) 0.077(6) 0.005(6) 0.027(5) 0.001(6) C25 0.138(7) 0.055(8) 0.073(8) 0.007(8) 0.029(5) 0.023(5) C26 0.315(13) 0.076(8) 0.093(8) 0.009(9) 0.069(7) 0.067(8) C27 0.356(15) 0.099(12) 0.091(9) 0.037(8) 0.067(9) 0.083(9) C28 0.230(11) 0.075(9) 0.099(10) 0.017(9) 0.032(7) 0.050(7) C29 0.122(7) 0.112(11) 0.043(8) -0.011(9) 0.018(4) 0.028(6) C30 0.126(7) 0.067(9) 0.075(9) -0.011(6) 0.025(5) 0.020(5) C31 0.085(6) 0.098(6) 0.097(6) -0.004(4) -0.004(4) 0.016(5) C32 0.061(6) 0.047(6) 0.058(7) 0.009(6) 0.019(6) 0.009(5) C33 0.051(6) 0.044(5) 0.052(8) 0.007(5) 0.003(5) -0.005(5) C34 0.074(7) 0.064(5) 0.055(7) 0.007(4) 0.006(5) -0.013(5) C35 0.069(6) 0.078(6) 0.087(6) 0.012(6) 0.016(7) -0.029(4) C36 0.090(7) 0.078(6) 0.068(7) 0.005(5) 0.005(5) -0.013(5) C37 0.091(7) 0.083(6) 0.064(8) 0.001(5) 0.018(6) -0.018(5) C38 0.081(6) 0.058(5) 0.058(6) 0.001(5) 0.018(7) -0.012(4) N1 0.064(5) 0.039(4) 0.078(4) -0.011(3) 0.020(3) -0.006(4) N2 0.153(8) 0.050(7) 0.146(6) 0.005(6) 0.093(5) -0.001(6) N3 0.077(4) 0.041(4) 0.056(4) 0.004(4) 0.013(4) -0.010(3) N4 0.217(8) 0.057(8) 0.102(10) 0.001(7) 0.018(6) 0.037(6) O1 0.094(4) 0.043(3) 0.083(3) 0.009(3) 0.038(3) 0.009(3) O2 0.088(4) 0.034(3) 0.112(4) 0.001(3) 0.026(3) 0.002(3) O3 0.149(5) 0.056(4) 0.161(5) 0.011(4) 0.064(4) 0.027(4) O4 0.243(8) 0.066(4) 0.285(8) 0.045(4) 0.199(7) 0.032(5) O5 0.147(4) 0.063(4) 0.093(4) 0.002(4) 0.052(3) -0.002(3) O6 0.076(3) 0.047(3) 0.077(3) 0.003(3) 0.018(3) -0.012(3) O7 0.328(9) 0.097(6) 0.113(5) -0.017(5) 0.036(5) 0.074(6) O8 0.357(10) 0.103(6) 0.109(6) -0.004(4) 0.096(6) 0.028(6) _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 C1 O1 1.430(6) . ? C1 C2 1.504(7) . ? C2 C3 1.528(7) . ? C3 N1 1.481(7) . ? C3 C12 1.530(7) . ? C3 C4 1.540(7) . ? C4 C5 1.523(7) . ? C5 O1 1.412(6) . ? C5 C6 1.507(7) . ? C6 C11 1.375(7) . ? C6 C7 1.382(8) . ? C7 C8 1.398(8) . ? C8 C9 1.371(8) . ? C9 C10 1.378(8) . ? C10 C11 1.365(8) . ? C10 N2 1.451(9) . ? C13 O2 1.229(7) . ? C13 N1 1.351(7) . ? C13 C14 1.498(9) . ? C14 C15 1.376(8) . ? C14 C19 1.388(8) . ? C16 C17 1.375(8) . ? C17 C18 1.373(8) . ? C20 O5 1.421(6) . ? C20 C21 1.517(8) . ? C21 C22 1.526(8) . ? C22 N3 1.474(7) . ? C22 C31 1.524(7) . ? C22 C23 1.542(7) . ? C23 C24 1.492(8) . ? C24 O5 1.424(7) . ? C24 C25 1.515(9) . ? C25 C26 1.365(9) . ? C26 C27 1.384(10) . ? C27 C28 1.353(10) . ? C28 C29 1.372(10) . ? C29 C30 1.375(9) . ? C29 N4 1.478(10) . ? C32 O6 1.238(7) . ? C32 N3 1.345(7) . ? C32 C33 1.486(8) . ? C33 C38 1.383(7) . ? C33 C34 1.384(8) . ? C34 C35 1.381(7) . ? C35 C36 1.385(8) . ? C36 C37 1.382(8) . ? C37 C38 1.349(7) . ? N2 O4 1.203(6) . ? N2 O3 1.216(6) . ? N4 O8 1.185(7) . ? N4 O7 1.197(7) . ? 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 O1 C1 C2 112.8(5) . . ? C1 C2 C3 111.6(5) . . ? N1 C3 C2 111.8(5) . . ? N1 C3 C12 109.4(5) . . ? C2 C3 C12 111.9(6) . . ? N1 C3 C4 106.9(6) . . ? C2 C3 C4 106.5(5) . . ? C12 C3 C4 110.3(6) . . ? C5 C4 C3 112.6(5) . . ? O1 C5 C6 108.0(6) . . ? O1 C5 C4 111.1(5) . . ? C6 C5 C4 112.4(6) . . ? C11 C6 C7 119.1(6) . . ? C11 C6 C5 116.7(9) . . ? C7 C6 C5 124.1(9) . . ? C6 C7 C8 120.3(6) . . ? C9 C8 C7 120.3(7) . . ? C8 C9 C10 118.0(7) . . ? C11 C10 C9 122.5(8) . . ? C11 C10 N2 121.0(9) . . ? C9 C10 N2 116.5(10) . . ? C10 C11 C6 119.7(7) . . ? O2 C13 N1 123.6(7) . . ? O2 C13 C14 121.8(8) . . ? N1 C13 C14 114.5(7) . . ? C15 C14 C19 118.3(7) . . ? C15 C14 C13 124.4(9) . . ? C19 C14 C13 117.2(10) . . ? C16 C15 C14 120.7(7) . . ? C15 C16 C17 120.2(7) . . ? C18 C17 C16 119.9(8) . . ? C19 C18 C17 119.7(7) . . ? C18 C19 C14 121.2(7) . . ? O5 C20 C21 111.3(6) . . ? C20 C21 C22 112.0(6) . . ? N3 C22 C31 109.7(6) . . ? N3 C22 C21 107.2(6) . . ? C31 C22 C21 112.1(6) . . ? N3 C22 C23 110.3(5) . . ? C31 C22 C23 110.3(6) . . ? C21 C22 C23 107.2(6) . . ? C24 C23 C22 114.0(6) . . ? O5 C24 C23 111.9(6) . . ? O5 C24 C25 107.3(7) . . ? C23 C24 C25 110.6(7) . . ? C30 C25 C26 117.6(8) . . ? C30 C25 C24 121.9(10) . . ? C26 C25 C24 120.4(11) . . ? C25 C26 C27 123.2(9) . . ? C28 C27 C26 119.4(9) . . ? C27 C28 C29 117.1(9) . . ? C28 C29 C30 123.9(8) . . ? C28 C29 N4 118.0(12) . . ? C30 C29 N4 118.1(12) . . ? C25 C30 C29 118.7(8) . . ? O6 C32 N3 122.4(7) . . ? O6 C32 C33 121.2(7) . . ? N3 C32 C33 116.4(7) . . ? C38 C33 C34 117.6(7) . . ? C38 C33 C32 119.5(9) . . ? C34 C33 C32 122.9(9) . . ? C35 C34 C33 120.6(7) . . ? C34 C35 C36 120.5(7) . . ? C37 C36 C35 118.7(7) . . ? C38 C37 C36 120.3(7) . . ? C37 C38 C33 122.3(7) . . ? C13 N1 C3 125.8(6) . . ? O4 N2 O3 122.0(8) . . ? O4 N2 C10 117.4(8) . . ? O3 N2 C10 120.6(8) . . ? C32 N3 C22 127.4(6) . . ? O8 N4 O7 121.5(10) . . ? O8 N4 C29 119.3(10) . . ? O7 N4 C29 119.1(9) . . ? C5 O1 C1 111.3(5) . . ? C20 O5 C24 111.1(5) . . ? _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 27.77 _diffrn_measured_fraction_theta_full 1.00 _refine_diff_density_max 0.146 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.035